# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2016 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_mm421 _database_code_depnum_ccdc_archive 'CCDC 1426599' _audit_update_record ; 2015-09-22 deposited with the CCDC. 2016-06-07 downloaded from the CCDC. ; _audit_creation_method SHELXL-2013 _chemical_name_systematic 1 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H60 Gd2 N6 O14' _chemical_formula_weight 1139.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.3263(3) _cell_length_b 8.3727(2) _cell_length_c 20.7908(5) _cell_angle_alpha 90 _cell_angle_beta 102.8720(11) _cell_angle_gamma 90 _cell_volume 2261.48(9) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9832 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 28.31 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_density_meas n/a _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.673 _exptl_crystal_F_000 1140 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.160 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.100 _exptl_absorpt_coefficient_mu 2.976 _shelx_estimated_absorpt_T_min 0.647 _shelx_estimated_absorpt_T_max 0.755 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5149 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS, Bruker (2003)' _exptl_special_details ; Data collection is performed with three batch runs at phi = 0.00 deg (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg (650 frames). Frame width = 0.30 deg in omega. Data is merged, corrected for decay (if any), and treated with multi-scan absorption corrections (if required). All symmetry-equivalent reflections are merged for centrosymmetric data. Friedel pairs are not merged for noncentrosymmetric data. ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 29945 _diffrn_reflns_av_unetI/netI 0.0205 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.257 _diffrn_reflns_theta_max 28.312 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_Laue_measured_fraction_full 0.988 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_point_group_measured_fraction_full 0.988 _reflns_number_total 5567 _reflns_number_gt 5333 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'APEX II, Bruker (2009)' _computing_cell_refinement 'APEX II, Bruker (2009)' _computing_data_reduction 'XPREP, Bruker (2009)' _computing_structure_solution 'SHELXS-03 (Sheldrick, 2003)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'SHELXTL, Bruker (2004)' _computing_publication_material 'SHELXTL, Bruker (2004)' _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0239P)^2^+3.1676P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 5567 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0214 _refine_ls_R_factor_gt 0.0200 _refine_ls_wR_factor_ref 0.0510 _refine_ls_wR_factor_gt 0.0503 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Gd1 Gd 0.36428(2) 0.97262(2) 0.52477(2) 0.01453(4) Uani 1 1 d . . . . . O1 O 0.29553(12) 0.97438(18) 0.61706(8) 0.0205(3) Uani 1 1 d . . . . . O2 O 0.14453(14) 1.0779(2) 0.66750(9) 0.0310(4) Uani 1 1 d . . . . . O3 O 0.53240(11) 0.87113(17) 0.53510(7) 0.0163(3) Uani 1 1 d . . . . . O4 O 0.19487(12) 0.8863(2) 0.48856(8) 0.0271(4) Uani 1 1 d . . . . . O5 O 0.34984(12) 0.8238(2) 0.42427(7) 0.0225(3) Uani 1 1 d . . . . . O6 O 0.45700(13) 1.1690(2) 0.59674(8) 0.0248(3) Uani 1 1 d . . . . . H6A H 0.4429 1.2118 0.6364 0.037 Uiso 1 1 d R U . . . H6B H 0.5314 1.1850 0.5960 0.037 Uiso 1 1 d R U . . . N4 N 0.40141(14) 0.7116(2) 0.58180(9) 0.0184(3) Uani 1 1 d . . . . . N5 N 0.49056(14) 0.6273(2) 0.57511(9) 0.0213(4) Uani 1 1 d . . . . . N6 N 0.72319(14) 0.7685(2) 0.53227(9) 0.0228(4) Uani 1 1 d . . . . . C1 C 0.23678(16) 0.8653(3) 0.63475(10) 0.0191(4) Uani 1 1 d . . . . . C2 C 0.15162(17) 0.9152(3) 0.66167(10) 0.0232(4) Uani 1 1 d . . . . . C3 C 0.08531(19) 0.8061(3) 0.67967(13) 0.0318(5) Uani 1 1 d . . . . . H3A H 0.0276 0.8424 0.6954 0.038 Uiso 1 1 calc R U . . . C4 C 0.1026(2) 0.6427(4) 0.67489(15) 0.0385(6) Uani 1 1 d . . . . . H4A H 0.0564 0.5678 0.6869 0.046 Uiso 1 1 calc R U . . . C5 C 0.1866(2) 0.5904(3) 0.65278(13) 0.0319(5) Uani 1 1 d . . . . . H5A H 0.1997 0.4790 0.6513 0.038 Uiso 1 1 calc R U . . . C6 C 0.25388(17) 0.6997(3) 0.63212(11) 0.0221(4) Uani 1 1 d . . . . . C7 C 0.0752(2) 1.1361(4) 0.70515(15) 0.0400(6) Uani 1 1 d . . . . . H7A H 0.0765 1.2531 0.7055 0.060 Uiso 1 1 calc R U . . . H7B H 0.0960 1.0962 0.7505 0.060 Uiso 1 1 calc R U . . . H7C H 0.0054 1.0990 0.6854 0.060 Uiso 1 1 calc R U . . . C8 C 0.34468(17) 0.6337(3) 0.61373(11) 0.0224(4) Uani 1 1 d . . . . . H8A H 0.3632 0.5266 0.6260 0.027 Uiso 1 1 calc R U . . . C9 C 0.54906(16) 0.7201(3) 0.54928(10) 0.0180(4) Uani 1 1 d . . . . . C10 C 0.64280(17) 0.6479(3) 0.53130(12) 0.0232(4) Uani 1 1 d . . . . . H10A H 0.6702 0.5616 0.5629 0.028 Uiso 1 1 calc R U . . . H10B H 0.6230 0.6001 0.4867 0.028 Uiso 1 1 calc R U . . . C11 C 0.7745(2) 0.8064(4) 0.60093(13) 0.0370(6) Uani 1 1 d . . . . . H11A H 0.7236 0.8474 0.6243 0.055 Uiso 1 1 calc R U . . . H11B H 0.8276 0.8874 0.6012 0.055 Uiso 1 1 calc R U . . . H11C H 0.8063 0.7095 0.6229 0.055 Uiso 1 1 calc R U . . . C12 C 0.7991(2) 0.7084(4) 0.49646(16) 0.0410(7) Uani 1 1 d . . . . . H12A H 0.7645 0.6837 0.4508 0.062 Uiso 1 1 calc R U . . . H12B H 0.8315 0.6115 0.5181 0.062 Uiso 1 1 calc R U . . . H12C H 0.8519 0.7900 0.4966 0.062 Uiso 1 1 calc R U . . . C13 C 0.14611(17) 0.7835(3) 0.44940(12) 0.0258(5) Uani 1 1 d . . . . . C14 C 0.18285(18) 0.7135(3) 0.39795(12) 0.0278(5) Uani 1 1 d . . . . . H14A H 0.1383 0.6437 0.3687 0.033 Uiso 1 1 calc R U . . . C15 C 0.28107(17) 0.7402(3) 0.38705(10) 0.0214(4) Uani 1 1 d . . . . . C16 C 0.0417(2) 0.7387(4) 0.45990(15) 0.0433(7) Uani 1 1 d . . . . . H16A H 0.0474 0.7100 0.5063 0.065 Uiso 1 1 calc R U . . . H16B H 0.0150 0.6473 0.4318 0.065 Uiso 1 1 calc R U . . . H16C H -0.0053 0.8295 0.4485 0.065 Uiso 1 1 calc R U . . . C17 C 0.3109(2) 0.6630(3) 0.32829(12) 0.0330(5) Uani 1 1 d . . . . . H17A H 0.3735 0.5996 0.3433 0.050 Uiso 1 1 calc R U . . . H17B H 0.3235 0.7460 0.2978 0.050 Uiso 1 1 calc R U . . . H17C H 0.2549 0.5934 0.3057 0.050 Uiso 1 1 calc R U . . . O7 O 0.35148(15) 1.2514(2) 0.68483(9) 0.0335(4) Uani 1 1 d . . . . . H7D H 0.3224 1.1647 0.6717 0.049(10) Uiso 1 1 calc R . . . . C18 C 0.3685(3) 1.2600(4) 0.75446(14) 0.0471(8) Uani 1 1 d . . . . . H18A H 0.4029 1.1613 0.7742 0.057 Uiso 1 1 calc R U . . . H18B H 0.3016 1.2689 0.7675 0.057 Uiso 1 1 calc R U . . . C19 C 0.4330(3) 1.3993(4) 0.77918(16) 0.0553(9) Uani 1 1 d . . . . . H19A H 0.4447 1.4034 0.8274 0.083 Uiso 1 1 calc R U . . . H19B H 0.3980 1.4971 0.7603 0.083 Uiso 1 1 calc R U . . . H19C H 0.4991 1.3900 0.7663 0.083 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Gd1 0.01098(6) 0.01925(6) 0.01491(5) 0.00080(3) 0.00618(4) -0.00001(3) O1 0.0196(8) 0.0240(8) 0.0212(7) -0.0011(6) 0.0118(6) -0.0024(6) O2 0.0275(9) 0.0317(9) 0.0406(10) -0.0001(8) 0.0220(8) 0.0048(7) O3 0.0143(7) 0.0177(7) 0.0189(6) 0.0024(5) 0.0083(5) 0.0005(5) O4 0.0157(8) 0.0413(10) 0.0257(8) -0.0015(7) 0.0076(6) -0.0038(7) O5 0.0169(7) 0.0304(9) 0.0215(7) -0.0045(6) 0.0070(6) -0.0040(6) O6 0.0220(8) 0.0328(9) 0.0220(7) -0.0074(6) 0.0102(6) -0.0071(7) N4 0.0166(8) 0.0191(8) 0.0215(8) 0.0019(7) 0.0090(7) 0.0009(7) N5 0.0196(9) 0.0189(9) 0.0290(9) 0.0037(7) 0.0129(7) 0.0039(7) N6 0.0151(9) 0.0278(10) 0.0287(9) 0.0065(7) 0.0116(7) 0.0046(7) C1 0.0148(9) 0.0296(11) 0.0144(8) 0.0003(8) 0.0068(7) -0.0020(8) C2 0.0196(10) 0.0313(11) 0.0208(9) 0.0007(9) 0.0090(8) 0.0008(9) C3 0.0215(12) 0.0440(15) 0.0363(13) 0.0006(11) 0.0197(10) -0.0010(10) C4 0.0317(14) 0.0412(15) 0.0520(16) 0.0011(12) 0.0290(13) -0.0104(11) C5 0.0324(13) 0.0275(12) 0.0426(14) 0.0025(10) 0.0229(11) -0.0036(10) C6 0.0205(11) 0.0269(11) 0.0221(10) 0.0012(8) 0.0119(8) -0.0024(8) C7 0.0376(15) 0.0448(16) 0.0457(15) 0.0001(12) 0.0264(13) 0.0116(12) C8 0.0228(11) 0.0216(10) 0.0260(10) 0.0011(8) 0.0122(9) -0.0013(8) C9 0.0158(10) 0.0212(10) 0.0186(9) -0.0001(7) 0.0074(7) 0.0019(7) C10 0.0203(10) 0.0202(10) 0.0330(11) 0.0047(9) 0.0144(9) 0.0042(8) C11 0.0259(13) 0.0486(16) 0.0319(13) 0.0142(11) -0.0032(10) -0.0008(11) C12 0.0281(14) 0.0408(15) 0.0644(19) 0.0117(13) 0.0320(13) 0.0127(11) C13 0.0124(10) 0.0360(13) 0.0280(11) 0.0062(9) 0.0020(8) -0.0020(9) C14 0.0170(11) 0.0307(12) 0.0334(12) -0.0043(9) 0.0007(9) -0.0059(9) C15 0.0194(10) 0.0229(11) 0.0204(10) 0.0008(8) 0.0016(8) 0.0005(8) C16 0.0181(12) 0.068(2) 0.0457(16) -0.0021(14) 0.0106(11) -0.0118(12) C17 0.0332(14) 0.0394(15) 0.0263(11) -0.0112(10) 0.0062(10) -0.0040(11) O7 0.0440(11) 0.0330(10) 0.0297(9) -0.0113(7) 0.0212(8) -0.0107(8) C18 0.066(2) 0.0509(18) 0.0279(13) -0.0045(12) 0.0177(13) -0.0165(16) C19 0.073(2) 0.051(2) 0.0340(15) -0.0039(14) -0.0039(15) -0.0150(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Gd1 O1 2.3032(14) . ? Gd1 O4 2.3300(16) . ? Gd1 O3 2.3608(14) . ? Gd1 O6 2.3758(16) . ? Gd1 O5 2.4035(15) . ? Gd1 O3 2.4333(14) 3_676 ? Gd1 N4 2.4831(18) . ? Gd1 N6 2.6166(19) 3_676 ? Gd1 Gd1 4.0021(2) 3_676 ? O1 C1 1.308(3) . ? O2 C2 1.373(3) . ? O2 C7 1.423(3) . ? O3 C9 1.306(3) . ? O3 Gd1 2.4333(13) 3_676 ? O4 C13 1.261(3) . ? O5 C15 1.270(3) . ? N4 C8 1.289(3) . ? N4 N5 1.415(2) . ? N5 C9 1.299(3) . ? N6 C10 1.469(3) . ? N6 C12 1.472(3) . ? N6 C11 1.473(3) . ? N6 Gd1 2.6166(19) 3_676 ? C1 C6 1.408(3) . ? C1 C2 1.435(3) . ? C2 C3 1.379(3) . ? C3 C4 1.395(4) . ? C4 C5 1.373(3) . ? C5 C6 1.414(3) . ? C6 C8 1.457(3) . ? C9 C10 1.508(3) . ? C13 C14 1.400(3) . ? C13 C16 1.503(3) . ? C14 C15 1.395(3) . ? C15 C17 1.511(3) . ? O7 C18 1.416(3) . ? C18 C19 1.471(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Gd1 O4 74.61(6) . . ? O1 Gd1 O3 118.17(5) . . ? O4 Gd1 O3 138.53(6) . . ? O1 Gd1 O6 73.65(5) . . ? O4 Gd1 O6 138.48(6) . . ? O3 Gd1 O6 80.90(5) . . ? O1 Gd1 O5 139.28(5) . . ? O4 Gd1 O5 70.98(5) . . ? O3 Gd1 O5 77.47(5) . . ? O6 Gd1 O5 146.72(5) . . ? O1 Gd1 O3 142.96(5) . 3_676 ? O4 Gd1 O3 128.28(5) . 3_676 ? O3 Gd1 O3 66.82(6) . 3_676 ? O6 Gd1 O3 71.10(5) . 3_676 ? O5 Gd1 O3 77.22(5) . 3_676 ? O1 Gd1 N4 71.45(6) . . ? O4 Gd1 N4 87.53(6) . . ? O3 Gd1 N4 63.61(5) . . ? O6 Gd1 N4 106.74(6) . . ? O5 Gd1 N4 85.84(6) . . ? O3 Gd1 N4 129.96(5) 3_676 . ? O1 Gd1 N6 98.78(6) . 3_676 ? O4 Gd1 N6 78.97(6) . 3_676 ? O3 Gd1 N6 131.09(5) . 3_676 ? O6 Gd1 N6 80.15(6) . 3_676 ? O5 Gd1 N6 95.40(6) . 3_676 ? O3 Gd1 N6 64.44(5) 3_676 3_676 ? N4 Gd1 N6 165.18(6) . 3_676 ? O1 Gd1 Gd1 139.80(4) . 3_676 ? O4 Gd1 Gd1 144.95(4) . 3_676 ? O3 Gd1 Gd1 33.98(3) . 3_676 ? O6 Gd1 Gd1 73.13(4) . 3_676 ? O5 Gd1 Gd1 74.78(4) . 3_676 ? O3 Gd1 Gd1 32.84(3) 3_676 3_676 ? N4 Gd1 Gd1 97.37(4) . 3_676 ? N6 Gd1 Gd1 97.20(4) 3_676 3_676 ? C1 O1 Gd1 127.15(13) . . ? C2 O2 C7 117.0(2) . . ? C9 O3 Gd1 118.64(12) . . ? C9 O3 Gd1 123.29(12) . 3_676 ? Gd1 O3 Gd1 113.18(6) . 3_676 ? C13 O4 Gd1 138.00(15) . . ? C15 O5 Gd1 136.27(14) . . ? C8 N4 N5 113.56(18) . . ? C8 N4 Gd1 127.88(15) . . ? N5 N4 Gd1 118.32(12) . . ? C9 N5 N4 109.66(17) . . ? C10 N6 C12 109.8(2) . . ? C10 N6 C11 109.90(18) . . ? C12 N6 C11 109.9(2) . . ? C10 N6 Gd1 108.27(13) . 3_676 ? C12 N6 Gd1 109.93(15) . 3_676 ? C11 N6 Gd1 108.94(16) . 3_676 ? O1 C1 C6 124.38(19) . . ? O1 C1 C2 118.8(2) . . ? C6 C1 C2 116.79(19) . . ? O2 C2 C3 124.9(2) . . ? O2 C2 C1 113.55(19) . . ? C3 C2 C1 121.5(2) . . ? C2 C3 C4 120.3(2) . . ? C5 C4 C3 119.8(2) . . ? C4 C5 C6 121.0(2) . . ? C1 C6 C5 120.4(2) . . ? C1 C6 C8 122.34(19) . . ? C5 C6 C8 117.0(2) . . ? N4 C8 C6 124.0(2) . . ? N5 C9 O3 125.82(19) . . ? N5 C9 C10 117.96(19) . . ? O3 C9 C10 116.18(18) . . ? N6 C10 C9 111.25(18) . . ? O4 C13 C14 124.1(2) . . ? O4 C13 C16 115.9(2) . . ? C14 C13 C16 119.9(2) . . ? C15 C14 C13 123.9(2) . . ? O5 C15 C14 124.4(2) . . ? O5 C15 C17 116.4(2) . . ? C14 C15 C17 119.2(2) . . ? O7 C18 C19 110.2(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N4 N5 C9 -172.7(2) . . . . ? Gd1 N4 N5 C9 12.4(2) . . . . ? Gd1 O1 C1 C6 43.5(3) . . . . ? Gd1 O1 C1 C2 -139.61(16) . . . . ? C7 O2 C2 C3 11.5(4) . . . . ? C7 O2 C2 C1 -168.2(2) . . . . ? O1 C1 C2 O2 -2.0(3) . . . . ? C6 C1 C2 O2 175.14(19) . . . . ? O1 C1 C2 C3 178.3(2) . . . . ? C6 C1 C2 C3 -4.5(3) . . . . ? O2 C2 C3 C4 -176.6(2) . . . . ? C1 C2 C3 C4 3.0(4) . . . . ? C2 C3 C4 C5 0.7(4) . . . . ? C3 C4 C5 C6 -2.6(4) . . . . ? O1 C1 C6 C5 179.5(2) . . . . ? C2 C1 C6 C5 2.6(3) . . . . ? O1 C1 C6 C8 4.8(3) . . . . ? C2 C1 C6 C8 -172.2(2) . . . . ? C4 C5 C6 C1 0.9(4) . . . . ? C4 C5 C6 C8 175.9(3) . . . . ? N5 N4 C8 C6 174.4(2) . . . . ? Gd1 N4 C8 C6 -11.3(3) . . . . ? C1 C6 C8 N4 -19.7(4) . . . . ? C5 C6 C8 N4 165.4(2) . . . . ? N4 N5 C9 O3 3.9(3) . . . . ? N4 N5 C9 C10 -173.61(18) . . . . ? Gd1 O3 C9 N5 -19.2(3) . . . . ? Gd1 O3 C9 N5 -172.67(17) 3_676 . . . ? Gd1 O3 C9 C10 158.36(14) . . . . ? Gd1 O3 C9 C10 4.9(2) 3_676 . . . ? C12 N6 C10 C9 -163.4(2) . . . . ? C11 N6 C10 C9 75.5(2) . . . . ? Gd1 N6 C10 C9 -43.4(2) 3_676 . . . ? N5 C9 C10 N6 -153.8(2) . . . . ? O3 C9 C10 N6 28.4(3) . . . . ? Gd1 O4 C13 C14 -20.4(4) . . . . ? Gd1 O4 C13 C16 160.5(2) . . . . ? O4 C13 C14 C15 5.1(4) . . . . ? C16 C13 C14 C15 -175.9(2) . . . . ? Gd1 O5 C15 C14 0.6(4) . . . . ? Gd1 O5 C15 C17 -177.88(16) . . . . ? C13 C14 C15 O5 3.9(4) . . . . ? C13 C14 C15 C17 -177.7(2) . . . . ? _refine_diff_density_max 1.141 _refine_diff_density_min -0.583 _refine_diff_density_rms 0.076 _shelxl_version_number 2013-4 _shelx_res_file ; TITL mm421 in P2(1)/c CELL 0.71073 13.32630 8.37270 20.79080 90.0000 102.8720 90.0000 ZERR 2.00 0.00030 0.00020 0.00050 0.0000 0.0011 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O GD UNIT 76 120 12 28 4 TEMP -73.150 SIZE 0.10 0.11 0.16 L.S. 80 ACTA CONF LIST 0 BOND FMAP 2 PLAN 5 OMIT -5 1 14 OMIT -8 8 6 OMIT -9 6 2 OMIT -4 3 9 OMIT 4 1 13 OMIT -6 1 6 OMIT -5 1 4 OMIT -6 3 2 OMIT -4 1 7 OMIT 8 1 8 OMIT 0 1 18 OMIT 5 5 8 OMIT 2 1 12 OMIT -4 1 2 OMIT 4 5 2 OMIT -12 1 14 OMIT -6 2 27 OMIT -2 6 20 OMIT -11 1 4 OMIT -5 2 6 OMIT -7 4 3 OMIT -12 8 2 OMIT 0 1 12 OMIT -12 7 5 OMIT -6 2 23 OMIT 6 9 5 OMIT -6 1 4 OMIT 9 6 2 OMIT 1 1 12 OMIT -10 4 5 OMIT -8 1 18 OMIT -9 1 1 OMIT 3 3 7 OMIT -2 7 19 OMIT -7 1 24 OMIT -5 2 9 OMIT -12 5 5 OMIT -9 7 1 OMIT -4 2 7 OMIT -7 1 20 OMIT -9 2 7 OMIT -4 2 1 OMIT -4 1 20 OMIT 7 3 9 OMIT -8 2 17 OMIT -9 1 6 OMIT 4 8 12 OMIT -9 8 2 OMIT 4 7 2 OMIT -4 2 17 WGHT 0.023900 3.167600 FVAR 0.10477 GD1 5 0.364278 0.972621 0.524774 11.00000 0.01098 0.01925 = 0.01491 0.00080 0.00618 -0.00001 O1 4 0.295526 0.974382 0.617064 11.00000 0.01962 0.02396 = 0.02122 -0.00113 0.01177 -0.00240 O2 4 0.144528 1.077886 0.667503 11.00000 0.02747 0.03172 = 0.04058 -0.00014 0.02200 0.00481 O3 4 0.532398 0.871130 0.535104 11.00000 0.01433 0.01772 = 0.01890 0.00236 0.00830 0.00051 O4 4 0.194866 0.886301 0.488562 11.00000 0.01570 0.04132 = 0.02567 -0.00154 0.00758 -0.00380 O5 4 0.349844 0.823780 0.424272 11.00000 0.01687 0.03036 = 0.02145 -0.00450 0.00698 -0.00398 O6 4 0.456998 1.168973 0.596743 11.00000 0.02204 0.03282 = 0.02200 -0.00744 0.01018 -0.00707 AFIX 3 H6A 2 0.442896 1.211754 0.636404 11.00000 -1.50000 H6B 2 0.531426 1.184977 0.596025 11.00000 -1.50000 AFIX 0 N4 3 0.401412 0.711580 0.581797 11.00000 0.01664 0.01912 = 0.02154 0.00186 0.00900 0.00087 N5 3 0.490558 0.627289 0.575106 11.00000 0.01963 0.01888 = 0.02903 0.00374 0.01289 0.00393 N6 3 0.723187 0.768517 0.532266 11.00000 0.01506 0.02777 = 0.02870 0.00650 0.01163 0.00460 C1 1 0.236782 0.865284 0.634750 11.00000 0.01482 0.02960 = 0.01444 0.00031 0.00681 -0.00204 C2 1 0.151618 0.915201 0.661667 11.00000 0.01959 0.03125 = 0.02084 0.00068 0.00902 0.00081 C3 1 0.085309 0.806110 0.679665 11.00000 0.02153 0.04397 = 0.03627 0.00065 0.01974 -0.00100 AFIX 43 H3A 2 0.027615 0.842450 0.695387 11.00000 -1.20000 AFIX 0 C4 1 0.102584 0.642661 0.674887 11.00000 0.03170 0.04119 = 0.05198 0.00108 0.02900 -0.01044 AFIX 43 H4A 2 0.056391 0.567796 0.686886 11.00000 -1.20000 AFIX 0 C5 1 0.186577 0.590357 0.652782 11.00000 0.03236 0.02752 = 0.04261 0.00245 0.02292 -0.00357 AFIX 43 H5A 2 0.199665 0.479027 0.651348 11.00000 -1.20000 AFIX 0 C6 1 0.253877 0.699697 0.632122 11.00000 0.02053 0.02687 = 0.02212 0.00120 0.01192 -0.00238 C7 1 0.075206 1.136086 0.705150 11.00000 0.03763 0.04483 = 0.04567 0.00007 0.02641 0.01161 AFIX 33 H7A 2 0.076518 1.253114 0.705475 11.00000 -1.50000 H7B 2 0.095985 1.096197 0.750487 11.00000 -1.50000 H7C 2 0.005383 1.099018 0.685412 11.00000 -1.50000 AFIX 0 C8 1 0.344684 0.633664 0.613733 11.00000 0.02280 0.02161 = 0.02600 0.00111 0.01216 -0.00127 AFIX 43 H8A 2 0.363237 0.526564 0.626039 11.00000 -1.20000 AFIX 0 C9 1 0.549063 0.720145 0.549280 11.00000 0.01579 0.02121 = 0.01860 -0.00014 0.00739 0.00185 C10 1 0.642797 0.647867 0.531297 11.00000 0.02028 0.02022 = 0.03303 0.00467 0.01435 0.00423 AFIX 23 H10A 2 0.670244 0.561640 0.562919 11.00000 -1.20000 H10B 2 0.623017 0.600084 0.486707 11.00000 -1.20000 AFIX 0 C11 1 0.774459 0.806361 0.600932 11.00000 0.02593 0.04856 = 0.03190 0.01422 -0.00323 -0.00080 AFIX 33 H11A 2 0.723601 0.847378 0.624314 11.00000 -1.50000 H11B 2 0.827624 0.887391 0.601217 11.00000 -1.50000 H11C 2 0.806256 0.709485 0.622938 11.00000 -1.50000 AFIX 0 C12 1 0.799110 0.708416 0.496456 11.00000 0.02809 0.04078 = 0.06441 0.01170 0.03195 0.01275 AFIX 33 H12A 2 0.764497 0.683745 0.450827 11.00000 -1.50000 H12B 2 0.831486 0.611473 0.518061 11.00000 -1.50000 H12C 2 0.851892 0.790019 0.496638 11.00000 -1.50000 AFIX 0 C13 1 0.146106 0.783477 0.449404 11.00000 0.01236 0.03603 = 0.02796 0.00625 0.00197 -0.00203 C14 1 0.182854 0.713500 0.397950 11.00000 0.01695 0.03072 = 0.03343 -0.00428 0.00072 -0.00591 AFIX 43 H14A 2 0.138280 0.643693 0.368742 11.00000 -1.20000 AFIX 0 C15 1 0.281066 0.740246 0.387046 11.00000 0.01942 0.02295 = 0.02041 0.00079 0.00164 0.00051 C16 1 0.041731 0.738684 0.459900 11.00000 0.01811 0.06778 = 0.04568 -0.00208 0.01055 -0.01179 AFIX 137 H16A 2 0.047375 0.709998 0.506268 11.00000 -1.50000 H16B 2 0.015009 0.647343 0.431795 11.00000 -1.50000 H16C 2 -0.005258 0.829499 0.448481 11.00000 -1.50000 AFIX 0 C17 1 0.310874 0.663014 0.328292 11.00000 0.03315 0.03945 = 0.02630 -0.01122 0.00620 -0.00398 AFIX 137 H17A 2 0.373521 0.599571 0.343294 11.00000 -1.50000 H17B 2 0.323498 0.746001 0.297804 11.00000 -1.50000 H17C 2 0.254931 0.593393 0.305683 11.00000 -1.50000 AFIX 0 O7 4 0.351478 1.251442 0.684827 11.00000 0.04397 0.03297 = 0.02971 -0.01128 0.02120 -0.01066 AFIX 83 H7D 2 0.322400 1.164654 0.671692 11.00000 0.04865 AFIX 0 C18 1 0.368457 1.260039 0.754460 11.00000 0.06610 0.05085 = 0.02788 -0.00451 0.01769 -0.01655 AFIX 23 H18A 2 0.402933 1.161255 0.774240 11.00000 -1.20000 H18B 2 0.301640 1.268936 0.767533 11.00000 -1.20000 AFIX 0 C19 1 0.432970 1.399258 0.779178 11.00000 0.07313 0.05147 = 0.03404 -0.00392 -0.00387 -0.01499 AFIX 33 H19A 2 0.444740 1.403425 0.827387 11.00000 -1.50000 H19B 2 0.397993 1.497065 0.760300 11.00000 -1.50000 H19C 2 0.499144 1.390008 0.766308 11.00000 -1.50000 AFIX 0 HKLF 4 REM mm421 in P2(1)/c REM R1 = 0.0200 for 5333 Fo > 4sig(Fo) and 0.0214 for all 5567 data REM 274 parameters refined using 0 restraints END WGHT 0.0099 2.3797 REM Highest difference peak 1.141, deepest hole -0.583, 1-sigma level 0.076 Q1 1 0.3647 0.8705 0.5278 11.00000 0.05 1.14 Q2 1 0.0942 0.9227 0.5765 11.00000 0.05 0.79 Q3 1 0.3463 1.0661 0.5199 11.00000 0.05 0.65 Q4 1 0.6997 0.8617 0.5222 11.00000 0.05 0.52 Q5 1 0.3492 0.9710 0.4805 11.00000 0.05 0.49 ; _shelx_res_checksum 59642 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_mm300 _database_code_depnum_ccdc_archive 'CCDC 1426600' _audit_update_record ; 2015-09-22 deposited with the CCDC. 2016-06-07 downloaded from the CCDC. ; _audit_creation_method SHELXL-2013 _chemical_name_systematic 2 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H60 Dy2 N6 O14' _chemical_formula_weight 1149.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.3404(5) _cell_length_b 8.3937(3) _cell_length_c 20.8588(8) _cell_angle_alpha 90 _cell_angle_beta 102.218(2) _cell_angle_gamma 90 _cell_volume 2282.77(15) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9982 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 28.22 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_density_meas n/a _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.673 _exptl_crystal_F_000 1148 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_min 0.060 _exptl_absorpt_coefficient_mu 3.316 _shelx_estimated_absorpt_T_min 0.692 _shelx_estimated_absorpt_T_max 0.826 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6100 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS, Bruker (2003)' _exptl_special_details ; Data collection is performed with three batch runs at phi = 0.00 deg (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg (650 frames). Frame width = 0.30 deg in omega. Data is merged, corrected for decay (if any), and treated with multi-scan absorption corrections (if required). All symmetry-equivalent reflections are merged for centrosymmetric data. Friedel pairs are not merged for noncentrosymmetric data. ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 35453 _diffrn_reflns_av_unetI/netI 0.0534 _diffrn_reflns_av_R_equivalents 0.0653 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.562 _diffrn_reflns_theta_max 28.407 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_Laue_measured_fraction_max 0.986 _diffrn_reflns_Laue_measured_fraction_full 0.988 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_point_group_measured_fraction_full 0.988 _reflns_number_total 5642 _reflns_number_gt 4290 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'APEX II, Bruker (2009)' _computing_cell_refinement 'APEX II, Bruker (2009)' _computing_data_reduction 'XPREP, Bruker (2009)' _computing_structure_solution 'SHELXS-03 (Sheldrick, 2003)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'SHELXTL, Bruker (2004)' _computing_publication_material 'SHELXTL, Bruker (2004)' _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+6.8197P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 5642 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0765 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1132 _refine_ls_wR_factor_gt 0.1028 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Dy1 Dy 0.36511(2) 0.97254(3) 0.52486(2) 0.02302(9) Uani 1 1 d . . . . . O1 O 0.2954(3) 0.9770(5) 0.6152(2) 0.0309(10) Uani 1 1 d . . . . . O2 O 0.1453(4) 1.0824(6) 0.6668(3) 0.0481(13) Uani 1 1 d . . . . . O3 O 0.5317(3) 0.8731(4) 0.5341(2) 0.0233(9) Uani 1 1 d . . . . . O4 O 0.1984(3) 0.8881(6) 0.4902(2) 0.0383(11) Uani 1 1 d . . . . . O5 O 0.3512(3) 0.8262(6) 0.4254(2) 0.0336(10) Uani 1 1 d . . . . . O6 O 0.4557(3) 1.1633(5) 0.5966(2) 0.0358(11) Uani 1 1 d . . . . . H6A H 0.5253 1.1733 0.5921 0.054 Uiso 1 1 d R U . . . H6B H 0.4489 1.1979 0.6415 0.054 Uiso 1 1 d R U . . . O7 O 0.3516(4) 1.2532(6) 0.6849(3) 0.0535(15) Uani 1 1 d . . . . . H7D H 0.3175 1.1706 0.6722 0.064 Uiso 1 1 calc R U . . . N1 N 0.4001(4) 0.7155(6) 0.5804(3) 0.0267(11) Uani 1 1 d . . . . . N2 N 0.4893(4) 0.6303(6) 0.5734(3) 0.0313(12) Uani 1 1 d . . . . . N3 N 0.7217(4) 0.7709(6) 0.5305(3) 0.0319(13) Uani 1 1 d . . . . . C1 C 0.2369(4) 0.8690(7) 0.6341(3) 0.0272(13) Uani 1 1 d . . . . . C2 C 0.1518(5) 0.9190(9) 0.6614(4) 0.0354(15) Uani 1 1 d . . . . . C3 C 0.0866(5) 0.8111(10) 0.6794(4) 0.050(2) Uani 1 1 d . . . . . H3A H 0.0295 0.8475 0.6959 0.060 Uiso 1 1 calc R U . . . C4 C 0.1023(6) 0.6498(10) 0.6742(4) 0.055(2) Uani 1 1 d . . . . . H4A H 0.0550 0.5761 0.6857 0.066 Uiso 1 1 calc R U . . . C5 C 0.1856(6) 0.5960(9) 0.6524(4) 0.048(2) Uani 1 1 d . . . . . H5A H 0.1985 0.4848 0.6515 0.058 Uiso 1 1 calc R U . . . C6 C 0.2532(5) 0.7056(8) 0.6312(3) 0.0316(15) Uani 1 1 d . . . . . C7 C 0.0772(7) 1.1413(11) 0.7056(5) 0.062(2) Uani 1 1 d . . . . . H7A H 0.0785 1.2581 0.7056 0.093 Uiso 1 1 calc R U . . . H7B H 0.0988 1.1022 0.7506 0.093 Uiso 1 1 calc R U . . . H7C H 0.0074 1.1043 0.6871 0.093 Uiso 1 1 calc R U . . . C8 C 0.3434(5) 0.6376(8) 0.6122(3) 0.0325(14) Uani 1 1 d . . . . . H8A H 0.3610 0.5303 0.6240 0.039 Uiso 1 1 calc R U . . . C9 C 0.5480(4) 0.7220(7) 0.5479(3) 0.0250(12) Uani 1 1 d . . . . . C10 C 0.6416(5) 0.6509(7) 0.5301(4) 0.0327(15) Uani 1 1 d . . . . . H10A H 0.6688 0.5655 0.5617 0.039 Uiso 1 1 calc R U . . . H10B H 0.6226 0.6025 0.4859 0.039 Uiso 1 1 calc R U . . . C11 C 0.7977(6) 0.7139(10) 0.4944(5) 0.058(2) Uani 1 1 d . . . . . H11A H 0.7635 0.6886 0.4492 0.087 Uiso 1 1 calc R U . . . H11B H 0.8312 0.6181 0.5157 0.087 Uiso 1 1 calc R U . . . H11C H 0.8492 0.7970 0.4941 0.087 Uiso 1 1 calc R U . . . C12 C 0.7728(6) 0.8084(10) 0.5991(4) 0.051(2) Uani 1 1 d . . . . . H12A H 0.7216 0.8462 0.6231 0.077 Uiso 1 1 calc R U . . . H12B H 0.8244 0.8916 0.5993 0.077 Uiso 1 1 calc R U . . . H12C H 0.8061 0.7124 0.6204 0.077 Uiso 1 1 calc R U . . . C13 C 0.1497(5) 0.7870(9) 0.4515(4) 0.0370(16) Uani 1 1 d . . . . . C14 C 0.1856(5) 0.7167(9) 0.4008(4) 0.0396(17) Uani 1 1 d . . . . . H14A H 0.1411 0.6467 0.3722 0.048 Uiso 1 1 calc R U . . . C15 C 0.2837(5) 0.7428(8) 0.3892(3) 0.0317(14) Uani 1 1 d . . . . . C16 C 0.0448(6) 0.7434(12) 0.4628(5) 0.062(2) Uani 1 1 d . . . . . H16A H 0.0313 0.8029 0.5005 0.093 Uiso 1 1 calc R U . . . H16B H 0.0424 0.6289 0.4714 0.093 Uiso 1 1 calc R U . . . H16C H -0.0074 0.7702 0.4236 0.093 Uiso 1 1 calc R U . . . C17 C 0.3133(6) 0.6679(10) 0.3301(4) 0.049(2) Uani 1 1 d . . . . . H17A H 0.3840 0.6972 0.3291 0.073 Uiso 1 1 calc R U . . . H17B H 0.2671 0.7062 0.2901 0.073 Uiso 1 1 calc R U . . . H17C H 0.3078 0.5518 0.3328 0.073 Uiso 1 1 calc R U . . . C18 C 0.3699(9) 1.2627(12) 0.7538(5) 0.075(3) Uani 1 1 d . . . . . H18A H 0.4028 1.1629 0.7730 0.090 Uiso 1 1 calc R U . . . H18B H 0.3037 1.2741 0.7677 0.090 Uiso 1 1 calc R U . . . C19 C 0.4349(10) 1.3956(13) 0.7779(6) 0.093(4) Uani 1 1 d . . . . . H19A H 0.4476 1.3978 0.8259 0.140 Uiso 1 1 calc R U . . . H19B H 0.4012 1.4948 0.7603 0.140 Uiso 1 1 calc R U . . . H19C H 0.5002 1.3849 0.7639 0.140 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Dy1 0.01818(13) 0.02607(14) 0.02675(16) 0.00072(13) 0.00915(10) -0.00055(12) O1 0.030(2) 0.029(2) 0.038(3) -0.0019(19) 0.0171(19) -0.0038(18) O2 0.046(3) 0.041(3) 0.066(4) -0.005(3) 0.032(3) 0.004(2) O3 0.023(2) 0.021(2) 0.028(2) 0.0040(16) 0.0110(17) 0.0004(15) O4 0.024(2) 0.051(3) 0.042(3) -0.003(2) 0.011(2) -0.006(2) O5 0.022(2) 0.049(3) 0.031(3) -0.009(2) 0.0075(19) -0.0055(19) O6 0.028(2) 0.045(3) 0.038(3) -0.013(2) 0.015(2) -0.0112(19) O7 0.071(4) 0.049(3) 0.048(4) -0.017(3) 0.029(3) -0.018(3) N1 0.029(3) 0.023(3) 0.032(3) 0.001(2) 0.014(2) -0.001(2) N2 0.026(3) 0.025(3) 0.048(4) 0.005(2) 0.019(2) 0.003(2) N3 0.022(3) 0.032(3) 0.045(4) 0.011(2) 0.016(2) 0.006(2) C1 0.023(3) 0.034(3) 0.026(3) 0.001(3) 0.009(2) -0.002(2) C2 0.028(3) 0.040(4) 0.042(4) -0.001(3) 0.015(3) 0.003(3) C3 0.032(4) 0.065(6) 0.063(6) 0.007(4) 0.033(4) 0.002(3) C4 0.049(5) 0.051(5) 0.078(6) 0.003(4) 0.043(5) -0.013(4) C5 0.047(4) 0.036(4) 0.070(6) 0.007(4) 0.032(4) -0.007(3) C6 0.022(3) 0.039(4) 0.038(4) 0.000(3) 0.017(3) -0.004(2) C7 0.052(5) 0.063(6) 0.083(7) 0.003(5) 0.039(5) 0.016(4) C8 0.034(3) 0.030(3) 0.038(4) 0.001(3) 0.016(3) -0.002(3) C9 0.023(3) 0.025(3) 0.028(4) 0.000(2) 0.009(2) -0.001(2) C10 0.029(3) 0.024(3) 0.049(4) 0.005(3) 0.017(3) 0.004(2) C11 0.039(4) 0.054(5) 0.091(7) 0.017(5) 0.039(5) 0.018(4) C12 0.030(4) 0.061(5) 0.058(6) 0.014(4) 0.000(4) 0.003(3) C13 0.016(3) 0.047(4) 0.049(5) 0.008(3) 0.009(3) -0.002(3) C14 0.022(3) 0.044(4) 0.049(5) -0.008(3) -0.002(3) -0.007(3) C15 0.028(3) 0.034(4) 0.030(4) -0.002(3) -0.001(3) -0.001(3) C16 0.030(4) 0.091(7) 0.065(6) 0.000(5) 0.012(4) -0.014(4) C17 0.047(4) 0.061(5) 0.037(5) -0.019(4) 0.007(3) -0.013(4) C18 0.113(9) 0.067(7) 0.050(6) -0.006(5) 0.030(6) -0.029(6) C19 0.130(11) 0.074(8) 0.070(8) -0.009(6) 0.006(7) -0.033(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Dy1 O1 2.271(4) . ? Dy1 O4 2.301(4) . ? Dy1 O3 2.344(4) . ? Dy1 O6 2.345(4) . ? Dy1 O3 2.408(4) 3_676 ? Dy1 O5 2.385(4) . ? Dy1 N1 2.446(5) . ? Dy1 N3 2.597(5) 3_676 ? Dy1 Dy1 3.9775(5) 3_676 ? O1 C1 1.311(7) . ? O2 C2 1.380(9) . ? O2 C7 1.427(8) . ? O3 C9 1.308(7) . ? O3 Dy1 2.408(4) 3_676 ? O4 C13 1.253(9) . ? O5 C15 1.258(7) . ? O7 C18 1.408(10) . ? N1 C8 1.286(7) . ? N1 N2 1.422(7) . ? N2 C9 1.290(7) . ? N3 C10 1.467(8) . ? N3 C11 1.465(8) . ? N3 C12 1.484(9) . ? N3 Dy1 2.597(5) 3_676 ? C1 C6 1.392(9) . ? C1 C2 1.437(8) . ? C2 C3 1.363(9) . ? C3 C4 1.377(11) . ? C4 C5 1.363(10) . ? C5 C6 1.423(9) . ? C6 C8 1.460(8) . ? C9 C10 1.501(8) . ? C13 C14 1.384(10) . ? C13 C16 1.512(9) . ? C14 C15 1.397(9) . ? C15 C17 1.508(9) . ? C18 C19 1.437(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Dy1 O4 74.18(16) . . ? O1 Dy1 O3 119.03(15) . . ? O4 Dy1 O3 138.87(16) . . ? O1 Dy1 O6 72.90(15) . . ? O4 Dy1 O6 138.13(16) . . ? O3 Dy1 O6 80.72(15) . . ? O1 Dy1 O3 142.50(15) . 3_676 ? O4 Dy1 O3 128.62(16) . 3_676 ? O3 Dy1 O3 66.37(16) . 3_676 ? O6 Dy1 O3 71.66(15) . 3_676 ? O1 Dy1 O5 139.48(15) . . ? O4 Dy1 O5 71.07(15) . . ? O3 Dy1 O5 77.66(14) . . ? O6 Dy1 O5 147.32(14) . . ? O3 Dy1 O5 77.32(14) 3_676 . ? O1 Dy1 N1 72.09(16) . . ? O4 Dy1 N1 87.23(17) . . ? O3 Dy1 N1 64.19(14) . . ? O6 Dy1 N1 106.24(17) . . ? O3 Dy1 N1 130.07(14) 3_676 . ? O5 Dy1 N1 85.95(17) . . ? O1 Dy1 N3 97.63(16) . 3_676 ? O4 Dy1 N3 78.77(17) . 3_676 ? O3 Dy1 N3 131.12(14) . 3_676 ? O6 Dy1 N3 80.70(18) . 3_676 ? O3 Dy1 N3 64.93(14) 3_676 3_676 ? O5 Dy1 N3 95.45(17) . 3_676 ? N1 Dy1 N3 164.59(16) . 3_676 ? O1 Dy1 Dy1 140.03(11) . 3_676 ? O4 Dy1 Dy1 145.27(12) . 3_676 ? O3 Dy1 Dy1 33.69(9) . 3_676 ? O6 Dy1 Dy1 73.41(10) . 3_676 ? O3 Dy1 Dy1 32.68(9) 3_676 3_676 ? O5 Dy1 Dy1 75.00(10) . 3_676 ? N1 Dy1 Dy1 97.66(11) . 3_676 ? N3 Dy1 Dy1 97.53(11) 3_676 3_676 ? C1 O1 Dy1 127.8(4) . . ? C2 O2 C7 116.7(6) . . ? C9 O3 Dy1 118.2(3) . . ? C9 O3 Dy1 123.2(3) . 3_676 ? Dy1 O3 Dy1 113.63(15) . 3_676 ? C13 O4 Dy1 138.3(4) . . ? C15 O5 Dy1 136.3(4) . . ? C8 N1 N2 113.2(5) . . ? C8 N1 Dy1 128.2(4) . . ? N2 N1 Dy1 118.3(3) . . ? C9 N2 N1 109.6(5) . . ? C10 N3 C11 110.8(6) . . ? C10 N3 C12 109.7(5) . . ? C11 N3 C12 109.8(6) . . ? C10 N3 Dy1 108.1(4) . 3_676 ? C11 N3 Dy1 109.5(4) . 3_676 ? C12 N3 Dy1 108.9(4) . 3_676 ? O1 C1 C6 124.1(5) . . ? O1 C1 C2 119.2(6) . . ? C6 C1 C2 116.7(5) . . ? C3 C2 O2 125.7(6) . . ? C3 C2 C1 121.2(6) . . ? O2 C2 C1 113.0(5) . . ? C2 C3 C4 121.0(6) . . ? C5 C4 C3 120.1(7) . . ? C4 C5 C6 120.3(7) . . ? C1 C6 C5 120.5(6) . . ? C1 C6 C8 122.9(5) . . ? C5 C6 C8 116.4(6) . . ? N1 C8 C6 123.4(6) . . ? N2 C9 O3 125.6(5) . . ? N2 C9 C10 118.3(5) . . ? O3 C9 C10 116.0(5) . . ? N3 C10 C9 111.7(5) . . ? O4 C13 C14 124.4(6) . . ? O4 C13 C16 115.8(7) . . ? C14 C13 C16 119.8(7) . . ? C13 C14 C15 123.6(6) . . ? O5 C15 C14 124.1(6) . . ? O5 C15 C17 116.4(6) . . ? C14 C15 C17 119.5(6) . . ? O7 C18 C19 111.2(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 N2 C9 -172.6(6) . . . . ? Dy1 N1 N2 C9 12.4(7) . . . . ? Dy1 O1 C1 C6 41.3(9) . . . . ? Dy1 O1 C1 C2 -140.4(5) . . . . ? C7 O2 C2 C3 12.5(11) . . . . ? C7 O2 C2 C1 -167.3(7) . . . . ? O1 C1 C2 C3 177.5(7) . . . . ? C6 C1 C2 C3 -4.1(11) . . . . ? O1 C1 C2 O2 -2.7(9) . . . . ? C6 C1 C2 O2 175.7(6) . . . . ? O2 C2 C3 C4 -177.6(8) . . . . ? C1 C2 C3 C4 2.2(13) . . . . ? C2 C3 C4 C5 1.9(14) . . . . ? C3 C4 C5 C6 -4.0(14) . . . . ? O1 C1 C6 C5 -179.6(7) . . . . ? C2 C1 C6 C5 2.0(10) . . . . ? O1 C1 C6 C8 5.9(11) . . . . ? C2 C1 C6 C8 -172.4(6) . . . . ? C4 C5 C6 C1 1.9(12) . . . . ? C4 C5 C6 C8 176.7(8) . . . . ? N2 N1 C8 C6 173.9(6) . . . . ? Dy1 N1 C8 C6 -11.8(10) . . . . ? C1 C6 C8 N1 -19.4(11) . . . . ? C5 C6 C8 N1 166.0(7) . . . . ? N1 N2 C9 O3 3.9(9) . . . . ? N1 N2 C9 C10 -174.1(6) . . . . ? Dy1 O3 C9 N2 -19.1(8) . . . . ? Dy1 O3 C9 N2 -172.6(5) 3_676 . . . ? Dy1 O3 C9 C10 158.9(4) . . . . ? Dy1 O3 C9 C10 5.4(7) 3_676 . . . ? C11 N3 C10 C9 -162.6(6) . . . . ? C12 N3 C10 C9 76.1(7) . . . . ? Dy1 N3 C10 C9 -42.5(6) 3_676 . . . ? N2 C9 C10 N3 -154.2(6) . . . . ? O3 C9 C10 N3 27.6(8) . . . . ? Dy1 O4 C13 C14 -19.5(12) . . . . ? Dy1 O4 C13 C16 160.9(6) . . . . ? O4 C13 C14 C15 4.3(12) . . . . ? C16 C13 C14 C15 -176.1(7) . . . . ? Dy1 O5 C15 C14 1.7(11) . . . . ? Dy1 O5 C15 C17 -178.2(5) . . . . ? C13 C14 C15 O5 3.7(12) . . . . ? C13 C14 C15 C17 -176.4(7) . . . . ? _refine_diff_density_max 2.207 _refine_diff_density_min -1.308 _refine_diff_density_rms 0.151 _shelxl_version_number 2013-4 _shelx_res_file ; TITL mm300 in P2(1)/c CELL 0.71073 13.34040 8.39370 20.85880 90.0000 102.2178 90.0000 ZERR 2.00 0.00050 0.00030 0.00080 0.0000 0.0022 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O DY UNIT 76 120 12 28 4 TEMP -73.15C SIZE 0.06 0.08 0.12 L.S. 80 LIST 0 ACTA CONF BOND FMAP 2 PLAN 5 OMIT -11 1 4 OMIT -6 1 6 OMIT -10 2 5 OMIT -14 1 4 OMIT 2 8 2 OMIT -9 6 2 OMIT -10 1 6 OMIT -17 1 8 OMIT -11 1 2 OMIT 2 8 0 OMIT -13 1 6 OMIT -14 1 2 OMIT -11 2 3 OMIT -14 2 5 OMIT -10 1 4 OMIT -10 2 7 OMIT -14 1 8 OMIT -17 1 6 OMIT -4 1 2 OMIT -5 8 2 OMIT -9 5 3 OMIT -9 2 9 OMIT -11 3 4 OMIT -1 9 1 OMIT -10 4 5 OMIT -13 1 8 OMIT -8 3 7 OMIT -11 3 2 OMIT 1 1 2 OMIT -13 1 10 OMIT 2 7 1 OMIT -9 7 1 OMIT 6 1 12 OMIT -5 5 3 OMIT -14 2 7 OMIT 11 1 2 OMIT -9 8 4 OMIT -13 2 9 OMIT -1 9 3 OMIT -15 1 4 OMIT -10 3 6 OMIT 6 9 3 OMIT -1 3 3 OMIT -7 3 2 OMIT -10 5 4 OMIT -2 9 1 OMIT -7 2 3 OMIT -1 8 2 OMIT -14 3 6 OMIT -14 1 6 WGHT 0.052900 6.819700 FVAR 0.08751 DY1 5 0.365112 0.972542 0.524861 11.00000 0.01818 0.02607 = 0.02675 0.00072 0.00915 -0.00055 O1 4 0.295396 0.976985 0.615207 11.00000 0.03035 0.02892 = 0.03785 -0.00194 0.01711 -0.00381 O2 4 0.145313 1.082419 0.666817 11.00000 0.04641 0.04082 = 0.06600 -0.00462 0.03228 0.00425 O3 4 0.531748 0.873131 0.534111 11.00000 0.02323 0.02077 = 0.02832 0.00401 0.01099 0.00037 O4 4 0.198357 0.888072 0.490195 11.00000 0.02398 0.05100 = 0.04182 -0.00339 0.01124 -0.00563 O5 4 0.351155 0.826173 0.425370 11.00000 0.02174 0.04884 = 0.03119 -0.00865 0.00753 -0.00554 O6 4 0.455721 1.163326 0.596564 11.00000 0.02796 0.04466 = 0.03831 -0.01258 0.01510 -0.01117 AFIX 3 H6A 2 0.525258 1.173265 0.592110 11.00000 -1.50000 H6B 2 0.448877 1.197930 0.641528 11.00000 -1.50000 AFIX 0 O7 4 0.351578 1.253168 0.684893 11.00000 0.07108 0.04937 = 0.04761 -0.01683 0.02945 -0.01845 AFIX 83 H7D 2 0.317546 1.170590 0.672224 11.00000 -1.20000 AFIX 0 N1 3 0.400061 0.715474 0.580354 11.00000 0.02881 0.02273 = 0.03216 0.00147 0.01436 -0.00132 N2 3 0.489288 0.630281 0.573356 11.00000 0.02635 0.02478 = 0.04751 0.00471 0.01860 0.00291 N3 3 0.721689 0.770930 0.530477 11.00000 0.02223 0.03198 = 0.04507 0.01071 0.01555 0.00570 C1 1 0.236905 0.868954 0.634143 11.00000 0.02320 0.03441 = 0.02591 0.00062 0.00930 -0.00237 C2 1 0.151753 0.919044 0.661415 11.00000 0.02800 0.03965 = 0.04203 -0.00082 0.01510 0.00350 C3 1 0.086574 0.811070 0.679434 11.00000 0.03180 0.06524 = 0.06336 0.00660 0.03326 0.00156 AFIX 43 H3A 2 0.029458 0.847544 0.695875 11.00000 -1.20000 AFIX 0 C4 1 0.102274 0.649836 0.674164 11.00000 0.04916 0.05066 = 0.07799 0.00277 0.04290 -0.01286 AFIX 43 H4A 2 0.055004 0.576112 0.685687 11.00000 -1.20000 AFIX 0 C5 1 0.185559 0.595970 0.652434 11.00000 0.04729 0.03582 = 0.06984 0.00684 0.03179 -0.00684 AFIX 43 H5A 2 0.198541 0.484807 0.651468 11.00000 -1.20000 AFIX 0 C6 1 0.253171 0.705609 0.631181 11.00000 0.02242 0.03944 = 0.03770 0.00031 0.01688 -0.00398 C7 1 0.077151 1.141346 0.705560 11.00000 0.05187 0.06252 = 0.08292 0.00327 0.03875 0.01587 AFIX 33 H7A 2 0.078473 1.258081 0.705583 11.00000 -1.50000 H7B 2 0.098797 1.102177 0.750631 11.00000 -1.50000 H7C 2 0.007363 1.104254 0.687078 11.00000 -1.50000 AFIX 0 C8 1 0.343354 0.637598 0.612203 11.00000 0.03359 0.02973 = 0.03783 0.00137 0.01564 -0.00246 AFIX 43 H8A 2 0.361049 0.530314 0.623986 11.00000 -1.20000 AFIX 0 C9 1 0.547953 0.722013 0.547862 11.00000 0.02314 0.02505 = 0.02812 -0.00041 0.00863 -0.00149 C10 1 0.641638 0.650945 0.530077 11.00000 0.02946 0.02352 = 0.04927 0.00550 0.01736 0.00354 AFIX 23 H10A 2 0.668821 0.565452 0.561691 11.00000 -1.20000 H10B 2 0.622594 0.602520 0.485891 11.00000 -1.20000 AFIX 0 C11 1 0.797681 0.713919 0.494409 11.00000 0.03919 0.05381 = 0.09134 0.01690 0.03931 0.01796 AFIX 33 H11A 2 0.763488 0.688554 0.449205 11.00000 -1.50000 H11B 2 0.831168 0.618100 0.515749 11.00000 -1.50000 H11C 2 0.849229 0.796961 0.494141 11.00000 -1.50000 AFIX 0 C12 1 0.772777 0.808448 0.599144 11.00000 0.03027 0.06148 = 0.05800 0.01444 0.00003 0.00288 AFIX 33 H12A 2 0.721593 0.846178 0.623091 11.00000 -1.50000 H12B 2 0.824420 0.891566 0.599305 11.00000 -1.50000 H12C 2 0.806057 0.712378 0.620384 11.00000 -1.50000 AFIX 0 C13 1 0.149656 0.787012 0.451549 11.00000 0.01627 0.04692 = 0.04866 0.00755 0.00893 -0.00241 C14 1 0.185616 0.716659 0.400767 11.00000 0.02195 0.04421 = 0.04857 -0.00843 -0.00194 -0.00728 AFIX 43 H14A 2 0.141130 0.646714 0.372188 11.00000 -1.20000 AFIX 0 C15 1 0.283686 0.742791 0.389204 11.00000 0.02820 0.03366 = 0.03025 -0.00220 -0.00052 -0.00072 C16 1 0.044774 0.743402 0.462758 11.00000 0.03008 0.09086 = 0.06541 -0.00026 0.01192 -0.01382 AFIX 33 H16A 2 0.031341 0.802900 0.500483 11.00000 -1.50000 H16B 2 0.042387 0.628862 0.471418 11.00000 -1.50000 H16C 2 -0.007406 0.770170 0.423641 11.00000 -1.50000 AFIX 0 C17 1 0.313256 0.667918 0.330142 11.00000 0.04724 0.06110 = 0.03710 -0.01909 0.00659 -0.01265 AFIX 33 H17A 2 0.384015 0.697163 0.329107 11.00000 -1.50000 H17B 2 0.267134 0.706162 0.290144 11.00000 -1.50000 H17C 2 0.307835 0.551772 0.332792 11.00000 -1.50000 AFIX 0 C18 1 0.369868 1.262685 0.753762 11.00000 0.11287 0.06749 = 0.04953 -0.00648 0.02991 -0.02942 AFIX 23 H18A 2 0.402765 1.162936 0.772999 11.00000 -1.20000 H18B 2 0.303734 1.274089 0.767674 11.00000 -1.20000 AFIX 0 C19 1 0.434900 1.395624 0.777851 11.00000 0.12960 0.07372 = 0.06967 -0.00858 0.00624 -0.03302 AFIX 33 H19A 2 0.447646 1.397833 0.825870 11.00000 -1.50000 H19B 2 0.401176 1.494814 0.760255 11.00000 -1.50000 H19C 2 0.500220 1.384871 0.763855 11.00000 -1.50000 REM ##### AFIX 0 HKLF 4 REM mm300 in P2(1)/c REM R1 = 0.0492 for 4290 Fo > 4sig(Fo) and 0.0765 for all 5642 data REM 271 parameters refined using 0 restraints END WGHT 0.0316 7.9540 REM Highest difference peak 2.207, deepest hole -1.308, 1-sigma level 0.151 Q1 1 0.0935 0.9188 0.5739 11.00000 0.05 2.21 Q2 1 0.4050 1.0764 0.5269 11.00000 0.05 1.34 Q3 1 0.3741 0.8655 0.5479 11.00000 0.05 1.24 Q4 1 0.3160 1.0082 0.5403 11.00000 0.05 1.22 Q5 1 0.3706 0.9783 0.5757 11.00000 0.05 1.19 ; _shelx_res_checksum 85735 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_mm424 _database_code_depnum_ccdc_archive 'CCDC 1426601' _audit_update_record ; 2015-09-22 deposited with the CCDC. 2016-06-07 downloaded from the CCDC. ; _audit_creation_method SHELXL-2013 _chemical_name_systematic 3 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H60 Ho2 N6 O14' _chemical_formula_weight 1154.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.2891(8) _cell_length_b 8.3607(6) _cell_length_c 20.7052(15) _cell_angle_alpha 90 _cell_angle_beta 102.908(4) _cell_angle_gamma 90 _cell_volume 2242.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 7947 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 28.38 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_density_meas n/a _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.710 _exptl_crystal_F_000 1152 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.110 _exptl_crystal_size_mid 0.030 _exptl_crystal_size_min 0.010 _exptl_absorpt_coefficient_mu 3.572 _shelx_estimated_absorpt_T_min 0.695 _shelx_estimated_absorpt_T_max 0.965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4817 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS, Bruker (2003)' _exptl_special_details ; Data collection is performed with three batch runs at phi = 0.00 deg (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg (650 frames). Frame width = 0.30 deg in omega. Data is merged, corrected for decay (if any), and treated with multi-scan absorption corrections (if required). All symmetry-equivalent reflections are merged for centrosymmetric data. Friedel pairs are not merged for noncentrosymmetric data. ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 29357 _diffrn_reflns_av_unetI/netI 0.0935 _diffrn_reflns_av_R_equivalents 0.1324 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.572 _diffrn_reflns_theta_max 28.389 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.974 _diffrn_measured_fraction_theta_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.974 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.974 _diffrn_reflns_point_group_measured_fraction_full 0.987 _reflns_number_total 5476 _reflns_number_gt 3951 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'APEX II, Bruker (2009)' _computing_cell_refinement 'APEX II, Bruker (2009)' _computing_data_reduction 'XPREP, Bruker (2009)' _computing_structure_solution 'SHELXS-03 (Sheldrick, 2003)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'SHELXTL, Bruker (2004)' _computing_publication_material 'SHELXTL, Bruker (2004)' _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0478P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 5476 _refine_ls_number_parameters 271 _refine_ls_number_restraints 408 _refine_ls_R_factor_all 0.0849 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1116 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ho1 Ho 0.36536(2) 0.97187(3) 0.52461(2) 0.01608(9) Uani 1 1 d . U . . . O1 O 0.2957(3) 0.9775(5) 0.6154(2) 0.0217(9) Uani 1 1 d . U . . . O2 O 0.1457(4) 1.0823(6) 0.6667(2) 0.0321(11) Uani 1 1 d . U . . . O3 O 0.5326(3) 0.8747(5) 0.5352(2) 0.0188(9) Uani 1 1 d . U . . . O4 O 0.3515(3) 0.8259(5) 0.4253(2) 0.0239(10) Uani 1 1 d . U . . . O5 O 0.1984(3) 0.8861(6) 0.4899(2) 0.0287(10) Uani 1 1 d . U . . . O6 O 0.4559(3) 1.1650(5) 0.5957(2) 0.0249(10) Uani 1 1 d . U . . . H6A H 0.4775 1.1772 0.6427 0.037 Uiso 1 1 d R U . . . H6B H 0.5044 1.2232 0.5730 0.037 Uiso 1 1 d R U . . . O7 O 0.3522(4) 1.2537(5) 0.6845(2) 0.0331(12) Uani 1 1 d . U . . . H7D H 0.3112 1.1785 0.6704 0.040 Uiso 1 1 calc R U . . . N1 N 0.4002(4) 0.7145(6) 0.5805(3) 0.0208(11) Uani 1 1 d . U . . . N2 N 0.4898(4) 0.6294(6) 0.5734(3) 0.0222(11) Uani 1 1 d . U . . . N3 N 0.7238(4) 0.7743(6) 0.5320(3) 0.0238(11) Uani 1 1 d . U . . . C1 C 0.2366(4) 0.8687(7) 0.6339(3) 0.0194(12) Uani 1 1 d . U . . . C2 C 0.1523(5) 0.9207(8) 0.6611(3) 0.0258(14) Uani 1 1 d . U . . . C3 C 0.0860(5) 0.8125(9) 0.6793(4) 0.0339(17) Uani 1 1 d . U . . . H3A H 0.0282 0.8498 0.6950 0.041 Uiso 1 1 calc R U . . . C4 C 0.1026(6) 0.6481(9) 0.6750(4) 0.0415(19) Uani 1 1 d . U . . . H4A H 0.0563 0.5743 0.6879 0.050 Uiso 1 1 calc R U . . . C5 C 0.1850(5) 0.5937(9) 0.6524(4) 0.0333(17) Uani 1 1 d . U . . . H5A H 0.1976 0.4820 0.6510 0.040 Uiso 1 1 calc R U . . . C6 C 0.2521(5) 0.7037(7) 0.6307(3) 0.0208(13) Uani 1 1 d . U . . . C7 C 0.0767(6) 1.1430(10) 0.7050(4) 0.043(2) Uani 1 1 d . U . . . H7A H 0.0783 1.2601 0.7048 0.064 Uiso 1 1 calc R U . . . H7B H 0.0982 1.1041 0.7507 0.064 Uiso 1 1 calc R U . . . H7C H 0.0064 1.1060 0.6858 0.064 Uiso 1 1 calc R U . . . C8 C 0.3442(5) 0.6366(8) 0.6129(3) 0.0224(13) Uani 1 1 d . U . . . H8A H 0.3635 0.5300 0.6261 0.027 Uiso 1 1 calc R U . . . C9 C 0.5493(4) 0.7229(7) 0.5490(3) 0.0185(12) Uani 1 1 d . U . . . C10 C 0.6438(5) 0.6508(7) 0.5309(3) 0.0231(13) Uani 1 1 d . U . . . H10A H 0.6719 0.5649 0.5628 0.028 Uiso 1 1 calc R U . . . H10B H 0.6243 0.6026 0.4862 0.028 Uiso 1 1 calc R U . . . C11 C 0.7753(5) 0.8103(9) 0.6012(4) 0.0367(16) Uani 1 1 d . U . . . H11A H 0.7241 0.8494 0.6249 0.055 Uiso 1 1 calc R U . . . H11B H 0.8281 0.8925 0.6019 0.055 Uiso 1 1 calc R U . . . H11C H 0.8077 0.7130 0.6226 0.055 Uiso 1 1 calc R U . . . C12 C 0.8002(5) 0.7152(9) 0.4960(4) 0.0371(18) Uani 1 1 d . U . . . H12A H 0.7657 0.6917 0.4500 0.056 Uiso 1 1 calc R U . . . H12B H 0.8325 0.6176 0.5173 0.056 Uiso 1 1 calc R U . . . H12C H 0.8532 0.7970 0.4967 0.056 Uiso 1 1 calc R U . . . C13 C 0.2835(5) 0.7411(7) 0.3880(3) 0.0241(13) Uani 1 1 d . U . . . C14 C 0.1859(5) 0.7129(8) 0.3991(3) 0.0273(14) Uani 1 1 d . U . . . H14A H 0.1417 0.6413 0.3702 0.033 Uiso 1 1 calc R U . . . C15 C 0.1490(5) 0.7840(8) 0.4504(4) 0.0278(14) Uani 1 1 d . U . . . C16 C 0.3141(6) 0.6622(9) 0.3295(3) 0.0340(16) Uani 1 1 d . U . . . H16A H 0.3847 0.6935 0.3283 0.051 Uiso 1 1 calc R U . . . H16B H 0.2667 0.6962 0.2884 0.051 Uiso 1 1 calc R U . . . H16C H 0.3106 0.5457 0.3338 0.051 Uiso 1 1 calc R U . . . C17 C 0.0448(6) 0.7381(10) 0.4615(4) 0.043(2) Uani 1 1 d . U . . . H17A H 0.0305 0.7996 0.4987 0.064 Uiso 1 1 calc R U . . . H17B H 0.0441 0.6236 0.4714 0.064 Uiso 1 1 calc R U . . . H17C H -0.0082 0.7614 0.4214 0.064 Uiso 1 1 calc R U . . . C18 C 0.3680(7) 1.2630(10) 0.7534(4) 0.047(2) Uani 1 1 d . U . . . H18A H 0.4001 1.1628 0.7736 0.056 Uiso 1 1 calc R U . . . H18B H 0.3007 1.2757 0.7659 0.056 Uiso 1 1 calc R U . . . C19 C 0.4353(7) 1.3997(11) 0.7788(4) 0.056(2) Uani 1 1 d . U . . . H19A H 0.4469 1.4033 0.8273 0.083 Uiso 1 1 calc R U . . . H19B H 0.4022 1.4992 0.7601 0.083 Uiso 1 1 calc R U . . . H19C H 0.5016 1.3874 0.7661 0.083 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ho1 0.01211(14) 0.01739(14) 0.02198(16) 0.00065(12) 0.01070(10) -0.00005(12) O1 0.020(2) 0.017(2) 0.033(2) -0.0014(17) 0.0172(18) -0.0012(16) O2 0.032(3) 0.033(2) 0.039(3) -0.0012(19) 0.024(2) 0.003(2) O3 0.016(2) 0.019(2) 0.024(2) -0.0010(15) 0.0118(17) -0.0007(15) O4 0.017(2) 0.029(2) 0.029(2) -0.0009(17) 0.0108(18) -0.0046(17) O5 0.018(2) 0.040(3) 0.032(3) -0.0022(19) 0.0135(19) -0.0023(18) O6 0.019(2) 0.035(3) 0.025(3) -0.0070(18) 0.0132(19) -0.0089(18) O7 0.041(3) 0.031(3) 0.035(3) -0.0105(19) 0.022(2) -0.013(2) N1 0.018(2) 0.022(3) 0.027(3) 0.0018(19) 0.015(2) 0.0003(18) N2 0.019(2) 0.020(3) 0.033(3) -0.001(2) 0.016(2) 0.0010(18) N3 0.012(2) 0.025(3) 0.038(3) 0.007(2) 0.013(2) 0.0018(19) C1 0.012(3) 0.026(3) 0.023(3) 0.001(2) 0.008(2) -0.001(2) C2 0.023(3) 0.031(3) 0.026(4) 0.002(2) 0.012(3) 0.004(2) C3 0.028(4) 0.038(3) 0.045(5) 0.003(3) 0.026(3) -0.001(3) C4 0.039(4) 0.037(4) 0.062(5) 0.005(3) 0.039(4) -0.004(3) C5 0.034(4) 0.026(3) 0.049(5) 0.001(3) 0.029(3) -0.008(3) C6 0.016(3) 0.023(3) 0.027(3) 0.002(2) 0.013(3) -0.002(2) C7 0.035(4) 0.047(5) 0.056(5) -0.001(4) 0.032(4) 0.009(3) C8 0.021(3) 0.023(3) 0.028(3) 0.003(2) 0.015(3) 0.002(2) C9 0.015(3) 0.019(3) 0.023(3) 0.000(2) 0.008(2) 0.001(2) C10 0.019(3) 0.015(3) 0.040(4) 0.004(2) 0.017(3) 0.003(2) C11 0.023(4) 0.042(4) 0.045(4) 0.012(3) 0.007(3) 0.000(3) C12 0.026(4) 0.035(4) 0.059(5) 0.011(3) 0.027(4) 0.011(3) C13 0.019(3) 0.023(3) 0.030(3) 0.001(2) 0.005(2) 0.001(2) C14 0.017(3) 0.030(4) 0.035(4) -0.003(3) 0.005(3) -0.005(2) C15 0.016(3) 0.035(4) 0.032(3) 0.006(2) 0.006(2) 0.001(2) C16 0.034(4) 0.037(4) 0.032(4) -0.010(3) 0.010(3) -0.004(3) C17 0.025(3) 0.055(5) 0.052(5) 0.002(4) 0.015(3) -0.009(3) C18 0.061(5) 0.047(5) 0.037(4) -0.006(3) 0.022(4) -0.012(4) C19 0.076(6) 0.045(5) 0.041(5) -0.007(4) 0.004(4) -0.015(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ho1 O1 2.274(4) . ? Ho1 O5 2.290(4) . ? Ho1 O3 2.330(4) . ? Ho1 O6 2.331(4) . ? Ho1 O4 2.363(4) . ? Ho1 O3 2.402(4) 3_676 ? Ho1 N1 2.438(5) . ? Ho1 N3 2.580(5) 3_676 ? Ho1 Ho1 3.9618(5) 3_676 ? O1 C1 1.313(7) . ? O2 C2 1.360(9) . ? O2 C7 1.434(7) . ? O3 C9 1.308(7) . ? O3 Ho1 2.402(4) 3_676 ? O4 C13 1.266(8) . ? O5 C15 1.261(8) . ? O7 C18 1.397(9) . ? N1 C8 1.286(7) . ? N1 N2 1.422(6) . ? N2 C9 1.294(7) . ? N3 C12 1.472(7) . ? N3 C11 1.474(9) . ? N3 C10 1.479(7) . ? N3 Ho1 2.580(5) 3_676 ? C1 C6 1.398(8) . ? C1 C2 1.430(8) . ? C2 C3 1.373(9) . ? C3 C4 1.398(10) . ? C4 C5 1.362(9) . ? C5 C6 1.422(8) . ? C6 C8 1.466(8) . ? C9 C10 1.513(8) . ? C13 C14 1.387(8) . ? C13 C16 1.514(9) . ? C14 C15 1.399(9) . ? C15 C17 1.503(9) . ? C18 C19 1.474(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ho1 O5 73.79(15) . . ? O1 Ho1 O3 119.04(15) . . ? O5 Ho1 O3 139.24(16) . . ? O1 Ho1 O6 73.22(14) . . ? O5 Ho1 O6 137.95(15) . . ? O3 Ho1 O6 80.53(14) . . ? O1 Ho1 O4 139.75(14) . . ? O5 Ho1 O4 71.55(14) . . ? O3 Ho1 O4 77.82(14) . . ? O6 Ho1 O4 146.78(13) . . ? O1 Ho1 O3 142.76(14) . 3_676 ? O5 Ho1 O3 128.67(16) . 3_676 ? O3 Ho1 O3 66.31(17) . 3_676 ? O6 Ho1 O3 71.59(14) . 3_676 ? O4 Ho1 O3 76.73(14) . 3_676 ? O1 Ho1 N1 72.26(15) . . ? O5 Ho1 N1 86.60(17) . . ? O3 Ho1 N1 64.62(14) . . ? O6 Ho1 N1 107.17(17) . . ? O4 Ho1 N1 85.81(16) . . ? O3 Ho1 N1 130.29(14) 3_676 . ? O1 Ho1 N3 97.33(15) . 3_676 ? O5 Ho1 N3 78.48(16) . 3_676 ? O3 Ho1 N3 131.39(14) . 3_676 ? O6 Ho1 N3 80.61(17) . 3_676 ? O4 Ho1 N3 95.22(17) . 3_676 ? O3 Ho1 N3 65.28(14) 3_676 3_676 ? N1 Ho1 N3 163.84(15) . 3_676 ? O1 Ho1 Ho1 140.19(11) . 3_676 ? O5 Ho1 Ho1 145.52(11) . 3_676 ? O3 Ho1 Ho1 33.73(9) . 3_676 ? O6 Ho1 Ho1 73.25(9) . 3_676 ? O4 Ho1 Ho1 74.74(9) . 3_676 ? O3 Ho1 Ho1 32.59(10) 3_676 3_676 ? N1 Ho1 Ho1 98.05(11) . 3_676 ? N3 Ho1 Ho1 97.77(10) 3_676 3_676 ? C1 O1 Ho1 127.4(4) . . ? C2 O2 C7 117.3(5) . . ? C9 O3 Ho1 118.1(3) . . ? C9 O3 Ho1 122.8(3) . 3_676 ? Ho1 O3 Ho1 113.69(17) . 3_676 ? C13 O4 Ho1 136.6(4) . . ? C15 O5 Ho1 138.0(4) . . ? C8 N1 N2 113.3(5) . . ? C8 N1 Ho1 128.6(4) . . ? N2 N1 Ho1 117.9(3) . . ? C9 N2 N1 109.7(5) . . ? C12 N3 C11 109.8(5) . . ? C12 N3 C10 109.4(5) . . ? C11 N3 C10 109.4(5) . . ? C12 N3 Ho1 110.2(4) . 3_676 ? C11 N3 Ho1 109.9(4) . 3_676 ? C10 N3 Ho1 108.2(4) . 3_676 ? O1 C1 C6 124.4(5) . . ? O1 C1 C2 118.5(5) . . ? C6 C1 C2 117.1(5) . . ? O2 C2 C3 125.0(5) . . ? O2 C2 C1 114.0(5) . . ? C3 C2 C1 121.0(6) . . ? C2 C3 C4 120.7(6) . . ? C5 C4 C3 120.0(6) . . ? C4 C5 C6 120.1(7) . . ? C1 C6 C5 120.9(5) . . ? C1 C6 C8 122.0(5) . . ? C5 C6 C8 116.7(6) . . ? N1 C8 C6 123.4(6) . . ? N2 C9 O3 125.6(5) . . ? N2 C9 C10 118.0(5) . . ? O3 C9 C10 116.3(5) . . ? N3 C10 C9 110.6(5) . . ? O4 C13 C14 124.1(6) . . ? O4 C13 C16 116.7(5) . . ? C14 C13 C16 119.1(6) . . ? C13 C14 C15 123.6(6) . . ? O5 C15 C14 124.1(6) . . ? O5 C15 C17 116.0(6) . . ? C14 C15 C17 119.9(7) . . ? O7 C18 C19 110.4(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 N2 C9 -170.9(6) . . . . ? Ho1 N1 N2 C9 13.6(6) . . . . ? Ho1 O1 C1 C6 41.0(8) . . . . ? Ho1 O1 C1 C2 -140.9(5) . . . . ? C7 O2 C2 C3 11.9(10) . . . . ? C7 O2 C2 C1 -168.1(6) . . . . ? O1 C1 C2 O2 -2.1(9) . . . . ? C6 C1 C2 O2 176.0(6) . . . . ? O1 C1 C2 C3 177.9(6) . . . . ? C6 C1 C2 C3 -4.0(10) . . . . ? O2 C2 C3 C4 -176.5(7) . . . . ? C1 C2 C3 C4 3.5(11) . . . . ? C2 C3 C4 C5 -0.2(12) . . . . ? C3 C4 C5 C6 -2.3(12) . . . . ? O1 C1 C6 C5 179.4(6) . . . . ? C2 C1 C6 C5 1.4(10) . . . . ? O1 C1 C6 C8 7.1(10) . . . . ? C2 C1 C6 C8 -171.0(6) . . . . ? C4 C5 C6 C1 1.7(11) . . . . ? C4 C5 C6 C8 174.5(7) . . . . ? N2 N1 C8 C6 175.5(6) . . . . ? Ho1 N1 C8 C6 -9.6(10) . . . . ? C1 C6 C8 N1 -21.7(10) . . . . ? C5 C6 C8 N1 165.6(7) . . . . ? N1 N2 C9 O3 2.6(9) . . . . ? N1 N2 C9 C10 -173.9(5) . . . . ? Ho1 O3 C9 N2 -18.4(8) . . . . ? Ho1 O3 C9 N2 -170.8(5) 3_676 . . . ? Ho1 O3 C9 C10 158.1(4) . . . . ? Ho1 O3 C9 C10 5.7(7) 3_676 . . . ? C12 N3 C10 C9 -163.3(6) . . . . ? C11 N3 C10 C9 76.4(6) . . . . ? Ho1 N3 C10 C9 -43.2(6) 3_676 . . . ? N2 C9 C10 N3 -155.5(6) . . . . ? O3 C9 C10 N3 27.7(8) . . . . ? Ho1 O4 C13 C14 1.0(11) . . . . ? Ho1 O4 C13 C16 -176.7(4) . . . . ? O4 C13 C14 C15 4.5(11) . . . . ? C16 C13 C14 C15 -177.8(7) . . . . ? Ho1 O5 C15 C14 -18.5(12) . . . . ? Ho1 O5 C15 C17 160.8(5) . . . . ? C13 C14 C15 O5 3.4(11) . . . . ? C13 C14 C15 C17 -176.0(7) . . . . ? _refine_diff_density_max 3.222 _refine_diff_density_min -1.352 _refine_diff_density_rms 0.219 _shelxl_version_number 2013-4 _shelx_res_file ; TITL mm424 in P2(1)/c CELL 0.71073 13.28910 8.36070 20.70520 90.0000 102.9084 90.0000 ZERR 2.00 0.00080 0.00060 0.00150 0.0000 0.0035 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O Ho UNIT 76 120 12 28 4 TEMP -73.150 SIZE 0.01 0.03 0.11 L.S. 80 ACTA CONF BOND FMAP 2 PLAN 5 LIST 0 SIMU RIGU OMIT -15 2 3 OMIT -14 4 5 OMIT -14 3 8 OMIT -14 3 4 OMIT -14 3 6 OMIT -17 3 8 OMIT 14 3 10 OMIT -14 1 6 OMIT -14 4 7 OMIT -15 1 4 OMIT -15 1 6 OMIT -17 2 9 OMIT -17 2 7 OMIT -15 2 5 OMIT -14 1 4 OMIT -14 3 10 OMIT -16 2 9 OMIT -15 2 7 OMIT 11 3 13 OMIT -17 1 10 OMIT 11 3 12 OMIT -17 2 5 OMIT -14 3 2 OMIT -16 1 10 OMIT -14 2 9 OMIT 3 0 24 OMIT -15 3 11 OMIT 2 0 24 OMIT -15 3 2 OMIT -14 2 7 OMIT -14 2 5 OMIT -15 4 8 OMIT -17 1 6 OMIT -15 5 9 OMIT -15 3 4 OMIT 11 3 11 OMIT -16 1 12 OMIT 1 1 26 OMIT -17 3 6 OMIT 2 0 22 OMIT -17 1 8 OMIT 3 1 25 OMIT -15 3 9 OMIT 11 3 14 OMIT -15 5 7 OMIT 13 7 1 OMIT -15 5 2 OMIT -15 3 6 OMIT -15 4 1 OMIT -17 1 4 WGHT 0.047800 FVAR 0.08642 HO1 5 0.365360 0.971866 0.524613 11.00000 0.01211 0.01739 = 0.02198 0.00065 0.01070 -0.00005 O1 4 0.295685 0.977508 0.615422 11.00000 0.02002 0.01736 = 0.03289 -0.00140 0.01717 -0.00119 O2 4 0.145712 1.082304 0.666664 11.00000 0.03197 0.03337 = 0.03864 -0.00116 0.02410 0.00265 O3 4 0.532563 0.874653 0.535188 11.00000 0.01624 0.01925 = 0.02434 -0.00098 0.01177 -0.00070 O4 4 0.351491 0.825932 0.425291 11.00000 0.01662 0.02886 = 0.02894 -0.00086 0.01078 -0.00456 O5 4 0.198368 0.886125 0.489909 11.00000 0.01755 0.03997 = 0.03228 -0.00216 0.01350 -0.00225 O6 4 0.455892 1.165046 0.595730 11.00000 0.01914 0.03464 = 0.02476 -0.00703 0.01323 -0.00886 AFIX 3 H6A 2 0.477452 1.177164 0.642672 11.00000 -1.50000 H6B 2 0.504366 1.223200 0.572990 11.00000 -1.50000 AFIX 0 O7 4 0.352247 1.253672 0.684494 11.00000 0.04051 0.03075 = 0.03467 -0.01051 0.02246 -0.01251 AFIX 83 H7D 2 0.311234 1.178535 0.670426 11.00000 -1.20000 AFIX 0 N1 3 0.400230 0.714519 0.580485 11.00000 0.01810 0.02216 = 0.02664 0.00177 0.01461 0.00027 N2 3 0.489760 0.629381 0.573423 11.00000 0.01855 0.01963 = 0.03314 -0.00086 0.01567 0.00103 N3 3 0.723826 0.774339 0.531951 11.00000 0.01185 0.02537 = 0.03766 0.00682 0.01278 0.00178 C1 1 0.236632 0.868730 0.633921 11.00000 0.01192 0.02588 = 0.02253 0.00109 0.00822 -0.00061 C2 1 0.152323 0.920733 0.661130 11.00000 0.02322 0.03129 = 0.02590 0.00219 0.01174 0.00366 C3 1 0.085969 0.812545 0.679336 11.00000 0.02795 0.03752 = 0.04468 0.00288 0.02622 -0.00130 AFIX 43 H3A 2 0.028227 0.849800 0.695014 11.00000 -1.20000 AFIX 0 C4 1 0.102553 0.648091 0.675029 11.00000 0.03853 0.03694 = 0.06183 0.00456 0.03867 -0.00437 AFIX 43 H4A 2 0.056332 0.574278 0.687912 11.00000 -1.20000 AFIX 0 C5 1 0.184956 0.593696 0.652367 11.00000 0.03376 0.02628 = 0.04923 0.00105 0.02890 -0.00793 AFIX 43 H5A 2 0.197581 0.482040 0.651015 11.00000 -1.20000 AFIX 0 C6 1 0.252120 0.703743 0.630728 11.00000 0.01579 0.02320 = 0.02720 0.00249 0.01298 -0.00214 C7 1 0.076686 1.142956 0.705044 11.00000 0.03536 0.04745 = 0.05611 -0.00086 0.03224 0.00906 AFIX 33 H7A 2 0.078343 1.260138 0.704834 11.00000 -1.50000 H7B 2 0.098153 1.104142 0.750716 11.00000 -1.50000 H7C 2 0.006384 1.106045 0.685815 11.00000 -1.50000 AFIX 0 C8 1 0.344200 0.636580 0.612948 11.00000 0.02085 0.02305 = 0.02775 0.00308 0.01497 0.00156 AFIX 43 H8A 2 0.363476 0.529997 0.626080 11.00000 -1.20000 AFIX 0 C9 1 0.549303 0.722910 0.548950 11.00000 0.01499 0.01936 = 0.02309 -0.00033 0.00848 0.00063 C10 1 0.643831 0.650768 0.530942 11.00000 0.01931 0.01514 = 0.03952 0.00437 0.01655 0.00328 AFIX 23 H10A 2 0.671901 0.564947 0.562840 11.00000 -1.20000 H10B 2 0.624322 0.602630 0.486200 11.00000 -1.20000 AFIX 0 C11 1 0.775261 0.810317 0.601159 11.00000 0.02325 0.04158 = 0.04527 0.01172 0.00741 -0.00020 AFIX 33 H11A 2 0.724122 0.849382 0.624937 11.00000 -1.50000 H11B 2 0.828102 0.892482 0.601905 11.00000 -1.50000 H11C 2 0.807749 0.713003 0.622640 11.00000 -1.50000 AFIX 0 C12 1 0.800182 0.715237 0.495971 11.00000 0.02646 0.03459 = 0.05876 0.01150 0.02734 0.01089 AFIX 33 H12A 2 0.765683 0.691710 0.449986 11.00000 -1.50000 H12B 2 0.832461 0.617626 0.517299 11.00000 -1.50000 H12C 2 0.853241 0.797025 0.496672 11.00000 -1.50000 AFIX 0 C13 1 0.283538 0.741112 0.388045 11.00000 0.01926 0.02281 = 0.02984 0.00075 0.00487 0.00101 C14 1 0.185910 0.712866 0.399091 11.00000 0.01700 0.02991 = 0.03452 -0.00314 0.00487 -0.00455 AFIX 43 H14A 2 0.141732 0.641350 0.370231 11.00000 -1.20000 AFIX 0 C15 1 0.148968 0.783955 0.450410 11.00000 0.01622 0.03524 = 0.03239 0.00573 0.00649 0.00120 C16 1 0.314083 0.662182 0.329473 11.00000 0.03409 0.03746 = 0.03161 -0.00984 0.00973 -0.00406 AFIX 33 H16A 2 0.384707 0.693515 0.328284 11.00000 -1.50000 H16B 2 0.266747 0.696221 0.288418 11.00000 -1.50000 H16C 2 0.310571 0.545704 0.333795 11.00000 -1.50000 AFIX 0 C17 1 0.044771 0.738141 0.461458 11.00000 0.02469 0.05510 = 0.05166 0.00215 0.01515 -0.00857 AFIX 33 H17A 2 0.030498 0.799551 0.498726 11.00000 -1.50000 H17B 2 0.044094 0.623618 0.471439 11.00000 -1.50000 H17C 2 -0.008236 0.761373 0.421415 11.00000 -1.50000 AFIX 0 C18 1 0.367962 1.263019 0.753398 11.00000 0.06135 0.04738 = 0.03724 -0.00609 0.02237 -0.01248 AFIX 23 H18A 2 0.400149 1.162751 0.773551 11.00000 -1.20000 H18B 2 0.300711 1.275709 0.765887 11.00000 -1.20000 AFIX 0 C19 1 0.435314 1.399683 0.778845 11.00000 0.07650 0.04492 = 0.04128 -0.00699 0.00434 -0.01493 AFIX 33 H19A 2 0.446879 1.403287 0.827256 11.00000 -1.50000 H19B 2 0.402205 1.499197 0.760081 11.00000 -1.50000 H19C 2 0.501628 1.387409 0.766115 11.00000 -1.50000 AFIX 0 HKLF 4 REM mm424 in P2(1)/c REM R1 = 0.0528 for 3951 Fo > 4sig(Fo) and 0.0849 for all 5476 data REM 271 parameters refined using 408 restraints END WGHT 0.0554 0.0000 REM Highest difference peak 3.222, deepest hole -1.352, 1-sigma level 0.219 Q1 1 0.3350 0.9758 0.4816 11.00000 0.05 3.22 Q2 1 0.3944 0.9782 0.5690 11.00000 0.05 3.10 Q3 1 0.3203 0.9730 0.5513 11.00000 0.05 2.53 Q4 1 0.4113 0.9715 0.4996 11.00000 0.05 2.52 Q5 1 0.3971 1.0861 0.5252 11.00000 0.05 1.78 ; _shelx_res_checksum 35260 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_mm377_5 _database_code_depnum_ccdc_archive 'CCDC 1426602' _audit_update_record ; 2015-09-22 deposited with the CCDC. 2016-06-07 downloaded from the CCDC. ; _audit_creation_method SHELXL-2013 _chemical_name_systematic 4 _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H30 Er N3 O7' _chemical_formula_weight 579.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5864(6) _cell_length_b 10.3618(8) _cell_length_c 13.2646(9) _cell_angle_alpha 74.961(3) _cell_angle_beta 86.219(3) _cell_angle_gamma 78.632(3) _cell_volume 1117.24(14) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9988 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 28.31 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_density_meas n/a _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.723 _exptl_crystal_F_000 578 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.160 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.080 _exptl_absorpt_coefficient_mu 3.799 _shelx_estimated_absorpt_T_min 0.582 _shelx_estimated_absorpt_T_max 0.751 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.495207 _exptl_absorpt_correction_T_max 0.745688 _exptl_absorpt_process_details 'SADABS, Bruker (2003)' _exptl_special_details ; Data collection is performed with four batch runs at phi = 0.00 deg (600 frames), at phi = 90.00 deg (600 frames), at phi = 180.00 deg (600 frames), and at phi = 270.00 deg (600 frames). A fifth batch run is collected at phi = 0.00 deg (50 frames) to monitor crystal and diffractometer stability. Frame width = 0.30 deg in omega. Data is merged, corrected for decay (if any), and treated with multi-scan absorption corrections (if required). All symmetry-equivalent reflections are merged for centrosymmetric data. Friedel pairs are not merged for noncentrosymmetric data. ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8337 _diffrn_reflns_av_unetI/netI 0.0441 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.072 _diffrn_reflns_theta_max 28.307 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.971 _diffrn_measured_fraction_theta_full 0.986 _diffrn_reflns_Laue_measured_fraction_max 0.971 _diffrn_reflns_Laue_measured_fraction_full 0.986 _diffrn_reflns_point_group_measured_fraction_max 0.971 _diffrn_reflns_point_group_measured_fraction_full 0.986 _reflns_number_total 5396 _reflns_number_gt 5125 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'APEX II, Bruker (2009)' _computing_cell_refinement 'APEX II, Bruker (2009)' _computing_data_reduction 'XPREP, Bruker (2009)' _computing_structure_solution 'SHELXS-03 (Sheldrick, 2003)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'SHELXTL, Bruker (2004)' _computing_publication_material 'SHELXTL, Bruker (2004)' _refine_special_details ; Refined as a 2-component twin. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0504P)^2^+4.5175P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 5396 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0987 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Er1 Er 0.45118(3) 0.54272(2) 0.13576(2) 0.01733(8) Uani 1 1 d . . . . . O1 O 0.4063(5) 0.7231(4) 0.2052(3) 0.0233(8) Uani 1 1 d . . . . . O2 O 0.4769(6) 0.8259(5) 0.3512(4) 0.0361(11) Uani 1 1 d . . . . . O3 O 0.3629(4) 0.5690(4) -0.0306(3) 0.0196(7) Uani 1 1 d . . . . . O4 O 0.3816(5) 0.4622(4) 0.3063(3) 0.0286(9) Uani 1 1 d . . . . . O5 O 0.3512(5) 0.3419(4) 0.1512(3) 0.0247(8) Uani 1 1 d . . . . . O6 O 0.5954(5) 0.7011(4) 0.0386(3) 0.0299(9) Uani 1 1 d . . . . . H6A H 0.6313 0.6874 -0.0282 0.045 Uiso 1 1 d R U . . . H6B H 0.5615 0.8008 0.0342 0.045 Uiso 1 1 d R U . . . O7 O 0.6671(6) 0.8517(6) 0.1566(5) 0.0461(13) Uani 1 1 d . . . . . H7D H 0.7462 0.8181 0.1248 0.069 Uiso 1 1 calc R U . . . N1 N 0.1740(5) 0.6480(5) 0.1062(4) 0.0229(9) Uani 1 1 d . . . . . N2 N 0.1010(5) 0.6336(5) 0.0188(4) 0.0228(9) Uani 1 1 d . . . . . N3 N 0.2805(6) 0.5705(5) -0.2221(4) 0.0257(10) Uani 1 1 d . . . . . C1 C 0.2889(7) 0.7588(5) 0.2649(4) 0.0217(10) Uani 1 1 d . . . . . C2 C 0.3191(7) 0.8154(6) 0.3472(5) 0.0261(11) Uani 1 1 d . . . . . C3 C 0.2017(8) 0.8573(7) 0.4140(5) 0.0361(14) Uani 1 1 d . . . . . H3A H 0.2272 0.8919 0.4693 0.043 Uiso 1 1 calc R U . . . C4 C 0.0444(8) 0.8482(7) 0.3996(6) 0.0365(15) Uani 1 1 d . . . . . H4A H -0.0373 0.8764 0.4455 0.044 Uiso 1 1 calc R U . . . C5 C 0.0083(7) 0.7990(7) 0.3196(5) 0.0310(13) Uani 1 1 d . . . . . H5A H -0.0991 0.7951 0.3097 0.037 Uiso 1 1 calc R U . . . C6 C 0.1279(7) 0.7537(6) 0.2511(4) 0.0238(11) Uani 1 1 d . . . . . C7 C 0.5134(9) 0.9019(9) 0.4191(7) 0.0449(18) Uani 1 1 d . . . . . H7A H 0.6278 0.9015 0.4159 0.067 Uiso 1 1 calc R U . . . H7B H 0.4820 0.8607 0.4908 0.067 Uiso 1 1 calc R U . . . H7C H 0.4554 0.9958 0.3973 0.067 Uiso 1 1 calc R U . . . C8 C 0.0783(7) 0.7125(6) 0.1633(5) 0.0244(11) Uani 1 1 d . . . . . H8A H -0.0314 0.7346 0.1471 0.029 Uiso 1 1 calc R U . . . C9 C 0.2090(6) 0.5908(5) -0.0445(4) 0.0196(10) Uani 1 1 d . . . . . C10 C 0.1567(6) 0.5565(6) -0.1391(5) 0.0257(11) Uani 1 1 d . . . . . H10A H 0.1372 0.4620 -0.1198 0.031 Uiso 1 1 calc R U . . . H10B H 0.0562 0.6183 -0.1652 0.031 Uiso 1 1 calc R U . . . C11 C 0.2812(9) 0.7157(7) -0.2687(6) 0.0369(14) Uani 1 1 d . . . . . H11A H 0.3634 0.7250 -0.3235 0.055 Uiso 1 1 calc R U . . . H11B H 0.3035 0.7582 -0.2146 0.055 Uiso 1 1 calc R U . . . H11C H 0.1772 0.7604 -0.2988 0.055 Uiso 1 1 calc R U . . . C12 C 0.2460(8) 0.5056(8) -0.3033(6) 0.0396(16) Uani 1 1 d . . . . . H12A H 0.3283 0.5138 -0.3581 0.059 Uiso 1 1 calc R U . . . H12B H 0.1422 0.5508 -0.3336 0.059 Uiso 1 1 calc R U . . . H12C H 0.2445 0.4092 -0.2717 0.059 Uiso 1 1 calc R U . . . C13 C 0.2836(7) 0.3909(6) 0.3550(5) 0.0263(11) Uani 1 1 d . . . . . C14 C 0.2270(7) 0.2957(6) 0.3164(5) 0.0289(12) Uani 1 1 d . . . . . H14A H 0.1578 0.2432 0.3600 0.035 Uiso 1 1 calc R U . . . C15 C 0.2659(7) 0.2729(6) 0.2177(5) 0.0244(11) Uani 1 1 d . . . . . C16 C 0.2285(10) 0.4127(8) 0.4599(6) 0.0437(17) Uani 1 1 d . . . . . H16A H 0.2789 0.4827 0.4747 0.066 Uiso 1 1 calc R U . . . H16B H 0.2577 0.3274 0.5136 0.066 Uiso 1 1 calc R U . . . H16C H 0.1128 0.4422 0.4601 0.066 Uiso 1 1 calc R U . . . C17 C 0.2042(8) 0.1641(6) 0.1851(5) 0.0320(13) Uani 1 1 d . . . . . H17A H 0.2404 0.1632 0.1137 0.048 Uiso 1 1 calc R U . . . H17B H 0.0878 0.1828 0.1881 0.048 Uiso 1 1 calc R U . . . H17C H 0.2441 0.0755 0.2324 0.048 Uiso 1 1 calc R U . . . C18 C 0.6533(12) 0.9928(8) 0.1321(8) 0.059(2) Uani 1 1 d . . . . . H18A H 0.6610 1.0219 0.1967 0.071 Uiso 1 1 calc R U . . . H18B H 0.5477 1.0363 0.1017 0.071 Uiso 1 1 calc R U . . . C19 C 0.7777(13) 1.0384(9) 0.0576(9) 0.065(3) Uani 1 1 d . . . . . H19A H 0.7656 1.1375 0.0428 0.097 Uiso 1 1 calc R U . . . H19B H 0.7682 1.0123 -0.0073 0.097 Uiso 1 1 calc R U . . . H19C H 0.8823 0.9957 0.0876 0.097 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Er1 0.01561(11) 0.02237(12) 0.01659(12) -0.00868(9) 0.00138(8) -0.00514(7) O1 0.0197(18) 0.035(2) 0.0201(19) -0.0140(16) 0.0044(14) -0.0080(16) O2 0.032(2) 0.046(3) 0.042(3) -0.030(2) -0.002(2) -0.010(2) O3 0.0133(16) 0.0281(18) 0.0200(19) -0.0103(15) 0.0031(13) -0.0057(14) O4 0.031(2) 0.033(2) 0.024(2) -0.0104(17) 0.0008(17) -0.0091(17) O5 0.028(2) 0.0255(19) 0.023(2) -0.0077(16) 0.0079(16) -0.0122(15) O6 0.041(2) 0.031(2) 0.025(2) -0.0122(17) 0.0133(18) -0.0199(18) O7 0.036(3) 0.051(3) 0.062(4) -0.029(3) 0.010(2) -0.016(2) N1 0.018(2) 0.027(2) 0.025(2) -0.0095(18) -0.0001(17) -0.0041(17) N2 0.019(2) 0.032(2) 0.023(2) -0.0147(19) -0.0005(17) -0.0060(18) N3 0.024(2) 0.035(3) 0.019(2) -0.012(2) 0.0007(18) -0.0037(19) C1 0.026(3) 0.023(2) 0.018(3) -0.007(2) 0.005(2) -0.009(2) C2 0.027(3) 0.030(3) 0.026(3) -0.015(2) 0.002(2) -0.004(2) C3 0.042(4) 0.048(4) 0.027(3) -0.022(3) 0.005(3) -0.012(3) C4 0.033(3) 0.048(4) 0.038(4) -0.028(3) 0.015(3) -0.010(3) C5 0.028(3) 0.038(3) 0.033(3) -0.020(3) 0.011(2) -0.008(2) C6 0.022(3) 0.029(3) 0.022(3) -0.010(2) 0.006(2) -0.005(2) C7 0.043(4) 0.061(5) 0.045(4) -0.034(4) -0.002(3) -0.013(3) C8 0.019(2) 0.034(3) 0.025(3) -0.014(2) 0.004(2) -0.009(2) C9 0.017(2) 0.024(2) 0.022(3) -0.011(2) -0.0003(19) -0.0073(19) C10 0.019(2) 0.039(3) 0.023(3) -0.014(2) 0.000(2) -0.007(2) C11 0.037(3) 0.032(3) 0.037(4) -0.005(3) 0.005(3) -0.004(3) C12 0.036(3) 0.063(4) 0.028(3) -0.027(3) -0.003(3) -0.006(3) C13 0.025(3) 0.033(3) 0.018(3) -0.005(2) 0.003(2) -0.002(2) C14 0.027(3) 0.035(3) 0.025(3) -0.006(2) 0.008(2) -0.011(2) C15 0.021(2) 0.025(3) 0.026(3) -0.005(2) 0.000(2) -0.004(2) C16 0.058(5) 0.052(4) 0.024(3) -0.013(3) 0.017(3) -0.018(4) C17 0.034(3) 0.029(3) 0.038(4) -0.011(3) 0.006(3) -0.014(2) C18 0.067(6) 0.038(4) 0.068(6) -0.017(4) 0.021(5) -0.003(4) C19 0.073(6) 0.035(4) 0.082(7) -0.007(4) 0.018(5) -0.016(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Er1 O1 2.248(4) . ? Er1 O4 2.282(4) . ? Er1 O3 2.312(4) . ? Er1 O6 2.319(4) . ? Er1 O5 2.360(4) . ? Er1 O3 2.376(4) 2_665 ? Er1 N1 2.426(5) . ? Er1 N3 2.566(5) 2_665 ? Er1 Er1 3.9270(5) 2_665 ? O1 C1 1.296(7) . ? O2 C2 1.385(7) . ? O2 C7 1.426(8) . ? O3 C9 1.313(6) . ? O3 Er1 2.376(4) 2_665 ? O4 C13 1.264(7) . ? O5 C15 1.272(7) . ? O7 C18 1.396(9) . ? N1 C8 1.289(7) . ? N1 N2 1.407(6) . ? N2 C9 1.300(7) . ? N3 C11 1.472(8) . ? N3 C10 1.479(7) . ? N3 C12 1.481(8) . ? N3 Er1 2.566(5) 2_665 ? C1 C6 1.419(8) . ? C1 C2 1.426(8) . ? C2 C3 1.378(8) . ? C3 C4 1.401(10) . ? C4 C5 1.367(9) . ? C5 C6 1.418(8) . ? C6 C8 1.454(8) . ? C9 C10 1.507(8) . ? C13 C14 1.398(9) . ? C13 C16 1.499(9) . ? C14 C15 1.398(8) . ? C15 C17 1.502(8) . ? C18 C19 1.469(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Er1 O4 74.16(15) . . ? O1 Er1 O3 119.09(14) . . ? O4 Er1 O3 140.34(14) . . ? O1 Er1 O6 72.01(15) . . ? O4 Er1 O6 138.14(15) . . ? O3 Er1 O6 78.97(15) . . ? O1 Er1 O5 138.66(14) . . ? O4 Er1 O5 71.62(15) . . ? O3 Er1 O5 77.11(14) . . ? O6 Er1 O5 148.27(14) . . ? O1 Er1 O3 141.95(13) . 2_665 ? O4 Er1 O3 128.18(15) . 2_665 ? O3 Er1 O3 66.24(15) . 2_665 ? O6 Er1 O3 72.56(14) . 2_665 ? O5 Er1 O3 78.86(13) . 2_665 ? O1 Er1 N1 73.26(15) . . ? O4 Er1 N1 87.19(16) . . ? O3 Er1 N1 64.79(15) . . ? O6 Er1 N1 105.64(17) . . ? O5 Er1 N1 82.52(15) . . ? O3 Er1 N1 130.27(15) 2_665 . ? O1 Er1 N3 96.97(15) . 2_665 ? O4 Er1 N3 77.01(16) . 2_665 ? O3 Er1 N3 131.55(14) . 2_665 ? O6 Er1 N3 83.34(17) . 2_665 ? O5 Er1 N3 97.26(16) . 2_665 ? O3 Er1 N3 65.47(14) 2_665 2_665 ? N1 Er1 N3 163.33(16) . 2_665 ? O1 Er1 Er1 139.71(11) . 2_665 ? O4 Er1 Er1 145.83(11) . 2_665 ? O3 Er1 Er1 33.63(9) . 2_665 ? O6 Er1 Er1 72.90(10) . 2_665 ? O5 Er1 Er1 75.62(10) . 2_665 ? O3 Er1 Er1 32.61(9) 2_665 2_665 ? N1 Er1 Er1 98.07(12) . 2_665 ? N3 Er1 Er1 98.01(11) 2_665 2_665 ? C1 O1 Er1 128.1(3) . . ? C2 O2 C7 116.9(5) . . ? C9 O3 Er1 118.0(3) . . ? C9 O3 Er1 122.3(3) . 2_665 ? Er1 O3 Er1 113.76(15) . 2_665 ? C13 O4 Er1 136.2(4) . . ? C15 O5 Er1 135.6(4) . . ? C8 N1 N2 113.4(5) . . ? C8 N1 Er1 128.5(4) . . ? N2 N1 Er1 118.0(3) . . ? C9 N2 N1 109.7(4) . . ? C11 N3 C10 109.4(5) . . ? C11 N3 C12 109.8(6) . . ? C10 N3 C12 109.2(5) . . ? C11 N3 Er1 109.1(4) . 2_665 ? C10 N3 Er1 107.3(3) . 2_665 ? C12 N3 Er1 112.0(4) . 2_665 ? O1 C1 C6 124.9(5) . . ? O1 C1 C2 118.7(5) . . ? C6 C1 C2 116.3(5) . . ? C3 C2 O2 124.1(5) . . ? C3 C2 C1 122.8(6) . . ? O2 C2 C1 113.0(5) . . ? C2 C3 C4 119.3(6) . . ? C5 C4 C3 120.1(6) . . ? C4 C5 C6 121.3(6) . . ? C5 C6 C1 120.0(5) . . ? C5 C6 C8 117.9(5) . . ? C1 C6 C8 121.9(5) . . ? N1 C8 C6 124.1(5) . . ? N2 C9 O3 125.0(5) . . ? N2 C9 C10 118.7(5) . . ? O3 C9 C10 116.2(5) . . ? N3 C10 C9 110.1(4) . . ? O4 C13 C14 123.7(6) . . ? O4 C13 C16 116.2(6) . . ? C14 C13 C16 120.1(6) . . ? C15 C14 C13 124.1(5) . . ? O5 C15 C14 123.1(5) . . ? O5 C15 C17 116.9(5) . . ? C14 C15 C17 120.0(5) . . ? O7 C18 C19 111.5(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 N2 C9 168.3(5) . . . . ? Er1 N1 N2 C9 -14.7(6) . . . . ? Er1 O1 C1 C6 -41.3(8) . . . . ? Er1 O1 C1 C2 142.7(4) . . . . ? C7 O2 C2 C3 -9.1(10) . . . . ? C7 O2 C2 C1 169.7(6) . . . . ? O1 C1 C2 C3 179.5(6) . . . . ? C6 C1 C2 C3 3.1(9) . . . . ? O1 C1 C2 O2 0.6(8) . . . . ? C6 C1 C2 O2 -175.7(5) . . . . ? O2 C2 C3 C4 176.8(7) . . . . ? C1 C2 C3 C4 -1.9(11) . . . . ? C2 C3 C4 C5 -0.3(11) . . . . ? C3 C4 C5 C6 1.3(11) . . . . ? C4 C5 C6 C1 0.0(10) . . . . ? C4 C5 C6 C8 -175.4(6) . . . . ? O1 C1 C6 C5 -178.2(6) . . . . ? C2 C1 C6 C5 -2.1(8) . . . . ? O1 C1 C6 C8 -3.0(9) . . . . ? C2 C1 C6 C8 173.1(5) . . . . ? N2 N1 C8 C6 -173.0(5) . . . . ? Er1 N1 C8 C6 10.4(9) . . . . ? C5 C6 C8 N1 -167.5(6) . . . . ? C1 C6 C8 N1 17.1(9) . . . . ? N1 N2 C9 O3 -2.1(8) . . . . ? N1 N2 C9 C10 174.7(5) . . . . ? Er1 O3 C9 N2 18.7(7) . . . . ? Er1 O3 C9 N2 169.8(4) 2_665 . . . ? Er1 O3 C9 C10 -158.1(4) . . . . ? Er1 O3 C9 C10 -7.1(6) 2_665 . . . ? C11 N3 C10 C9 -73.3(6) . . . . ? C12 N3 C10 C9 166.5(5) . . . . ? Er1 N3 C10 C9 44.9(5) 2_665 . . . ? N2 C9 C10 N3 154.7(5) . . . . ? O3 C9 C10 N3 -28.2(7) . . . . ? Er1 O4 C13 C14 26.1(9) . . . . ? Er1 O4 C13 C16 -154.0(5) . . . . ? O4 C13 C14 C15 -3.2(10) . . . . ? C16 C13 C14 C15 176.9(6) . . . . ? Er1 O5 C15 C14 -10.7(9) . . . . ? Er1 O5 C15 C17 168.3(4) . . . . ? C13 C14 C15 O5 -3.5(10) . . . . ? C13 C14 C15 C17 177.5(6) . . . . ? _refine_diff_density_max 2.124 _refine_diff_density_min -1.847 _refine_diff_density_rms 0.170 _shelxl_version_number 2013-4 _shelx_res_file ; TITL mm377_4 in P-1 CELL 0.71073 8.58640 10.36180 13.26460 74.9611 86.2190 78.6325 ZERR 2.00 0.00060 0.00080 0.00090 0.0027 0.0027 0.0029 LATT 1 SFAC C H N O ER UNIT 38 60 6 14 2 TEMP -73.150 SIZE 0.08 0.10 0.16 L.S. 80 ACTA CONF LIST 0 BOND FMAP 2 PLAN 5 OMIT 0 4 8 OMIT 1 4 1 OMIT -1 2 1 OMIT -1 2 5 OMIT -3 -2 2 OMIT 2 9 9 OMIT 0 4 4 OMIT -5 -7 10 OMIT -1 -5 3 OMIT 3 2 2 OMIT -4 -9 7 OMIT 1 5 4 OMIT 10 4 4 OMIT -5 -7 9 OMIT -2 -6 12 OMIT -2 -6 13 OMIT 8 10 8 OMIT 5 -3 8 OMIT 10 7 3 OMIT -2 -3 11 OMIT -8 -7 7 OMIT 1 5 1 OMIT 3 9 15 OMIT 4 12 7 OMIT 6 -3 5 OMIT 1 11 3 OMIT 3 -2 14 OMIT -2 -3 10 OMIT 0 7 7 OMIT -2 -3 12 OMIT -3 8 9 OMIT -3 -7 10 OMIT 9 4 8 OMIT -2 -3 8 OMIT -2 -3 9 OMIT 2 9 10 OMIT -7 -5 8 OMIT 6 -2 13 OMIT 2 0 0 OMIT 3 9 8 OMIT -4 -10 7 OMIT -6 -10 3 OMIT -6 4 2 OMIT 0 -2 6 OMIT 8 6 3 OMIT 4 -1 11 OMIT 8 -3 2 OMIT -6 -10 6 OMIT -5 -6 2 OMIT -2 -10 8 WGHT 0.050400 4.517500 BASF 0.17869 FVAR 0.43009 ER1 5 0.451184 0.542719 0.135755 11.00000 0.01561 0.02237 = 0.01659 -0.00868 0.00138 -0.00514 O1 4 0.406327 0.723119 0.205170 11.00000 0.01969 0.03479 = 0.02013 -0.01400 0.00443 -0.00802 O2 4 0.476870 0.825886 0.351201 11.00000 0.03161 0.04625 = 0.04240 -0.02982 -0.00209 -0.01024 O3 4 0.362948 0.568957 -0.030623 11.00000 0.01329 0.02808 = 0.02000 -0.01027 0.00310 -0.00572 O4 4 0.381648 0.462192 0.306264 11.00000 0.03131 0.03311 = 0.02441 -0.01042 0.00079 -0.00911 O5 4 0.351156 0.341926 0.151236 11.00000 0.02827 0.02548 = 0.02311 -0.00768 0.00790 -0.01218 O6 4 0.595444 0.701064 0.038626 11.00000 0.04100 0.03059 = 0.02488 -0.01224 0.01334 -0.01988 AFIX 3 H6A 2 0.631266 0.687380 -0.028203 11.00000 -1.50000 H6B 2 0.561461 0.800795 0.034236 11.00000 -1.50000 AFIX 0 O7 4 0.667140 0.851662 0.156604 11.00000 0.03585 0.05060 = 0.06210 -0.02871 0.01009 -0.01644 AFIX 143 H7D 2 0.746167 0.818055 0.124752 11.00000 -1.50000 AFIX 0 N1 3 0.174001 0.648018 0.106153 11.00000 0.01831 0.02703 = 0.02495 -0.00954 -0.00006 -0.00408 N2 3 0.101005 0.633555 0.018829 11.00000 0.01864 0.03207 = 0.02278 -0.01471 -0.00054 -0.00599 N3 3 0.280486 0.570455 -0.222140 11.00000 0.02448 0.03532 = 0.01944 -0.01228 0.00065 -0.00365 C1 1 0.288862 0.758805 0.264859 11.00000 0.02627 0.02292 = 0.01808 -0.00692 0.00471 -0.00885 C2 1 0.319143 0.815410 0.347194 11.00000 0.02699 0.02985 = 0.02551 -0.01531 0.00201 -0.00449 C3 1 0.201699 0.857269 0.414006 11.00000 0.04169 0.04761 = 0.02684 -0.02236 0.00522 -0.01158 AFIX 43 H3A 2 0.227155 0.891889 0.469277 11.00000 -1.20000 AFIX 0 C4 1 0.044378 0.848242 0.399579 11.00000 0.03266 0.04793 = 0.03762 -0.02820 0.01545 -0.00969 AFIX 43 H4A 2 -0.037315 0.876374 0.445457 11.00000 -1.20000 AFIX 0 C5 1 0.008277 0.799035 0.319617 11.00000 0.02778 0.03811 = 0.03250 -0.01996 0.01089 -0.00785 AFIX 43 H5A 2 -0.099113 0.795130 0.309731 11.00000 -1.20000 AFIX 0 C6 1 0.127934 0.753701 0.251126 11.00000 0.02236 0.02889 = 0.02165 -0.01042 0.00586 -0.00497 C7 1 0.513373 0.901901 0.419104 11.00000 0.04259 0.06068 = 0.04502 -0.03431 -0.00183 -0.01341 AFIX 33 H7A 2 0.627821 0.901481 0.415856 11.00000 -1.50000 H7B 2 0.482015 0.860662 0.490808 11.00000 -1.50000 H7C 2 0.455373 0.995810 0.397322 11.00000 -1.50000 AFIX 0 C8 1 0.078346 0.712546 0.163305 11.00000 0.01904 0.03373 = 0.02535 -0.01405 0.00438 -0.00900 AFIX 43 H8A 2 -0.031370 0.734599 0.147059 11.00000 -1.20000 AFIX 0 C9 1 0.209006 0.590837 -0.044544 11.00000 0.01674 0.02417 = 0.02224 -0.01070 -0.00032 -0.00733 C10 1 0.156691 0.556484 -0.139145 11.00000 0.01937 0.03893 = 0.02268 -0.01376 0.00012 -0.00658 AFIX 23 H10A 2 0.137174 0.462049 -0.119837 11.00000 -1.20000 H10B 2 0.056212 0.618254 -0.165169 11.00000 -1.20000 AFIX 0 C11 1 0.281229 0.715656 -0.268655 11.00000 0.03724 0.03245 = 0.03674 -0.00460 0.00520 -0.00367 AFIX 33 H11A 2 0.363446 0.725047 -0.323541 11.00000 -1.50000 H11B 2 0.303520 0.758169 -0.214584 11.00000 -1.50000 H11C 2 0.177217 0.760440 -0.298814 11.00000 -1.50000 AFIX 0 C12 1 0.245970 0.505570 -0.303251 11.00000 0.03576 0.06260 = 0.02821 -0.02680 -0.00253 -0.00629 AFIX 33 H12A 2 0.328331 0.513844 -0.358096 11.00000 -1.50000 H12B 2 0.142200 0.550771 -0.333613 11.00000 -1.50000 H12C 2 0.244540 0.409160 -0.271714 11.00000 -1.50000 AFIX 0 C13 1 0.283646 0.390866 0.355024 11.00000 0.02518 0.03335 = 0.01797 -0.00534 0.00265 -0.00212 C14 1 0.227022 0.295692 0.316417 11.00000 0.02738 0.03472 = 0.02457 -0.00569 0.00799 -0.01078 AFIX 43 H14A 2 0.157769 0.243234 0.360022 11.00000 -1.20000 AFIX 0 C15 1 0.265904 0.272872 0.217689 11.00000 0.02060 0.02537 = 0.02604 -0.00522 0.00003 -0.00351 C16 1 0.228484 0.412694 0.459920 11.00000 0.05791 0.05222 = 0.02360 -0.01284 0.01710 -0.01806 AFIX 33 H16A 2 0.278897 0.482709 0.474652 11.00000 -1.50000 H16B 2 0.257672 0.327419 0.513608 11.00000 -1.50000 H16C 2 0.112810 0.442227 0.460100 11.00000 -1.50000 AFIX 0 C17 1 0.204169 0.164141 0.185143 11.00000 0.03372 0.02877 = 0.03756 -0.01105 0.00602 -0.01392 AFIX 33 H17A 2 0.240354 0.163177 0.113666 11.00000 -1.50000 H17B 2 0.087770 0.182823 0.188090 11.00000 -1.50000 H17C 2 0.244092 0.075461 0.232432 11.00000 -1.50000 AFIX 0 C18 1 0.653310 0.992822 0.132078 11.00000 0.06729 0.03761 = 0.06778 -0.01700 0.02132 -0.00331 AFIX 23 H18A 2 0.661029 1.021865 0.196746 11.00000 -1.20000 H18B 2 0.547733 1.036291 0.101696 11.00000 -1.20000 AFIX 0 C19 1 0.777693 1.038371 0.057599 11.00000 0.07332 0.03493 = 0.08191 -0.00689 0.01787 -0.01611 AFIX 33 H19A 2 0.765576 1.137503 0.042801 11.00000 -1.50000 H19B 2 0.768169 1.012262 -0.007324 11.00000 -1.50000 H19C 2 0.882331 0.995742 0.087621 11.00000 -1.50000 AFIX 0 HKLF 5 REM mm377_4 in P-1 REM R1 = 0.0381 for 5125 Fo > 4sig(Fo) and 0.0421 for all 5396 data REM 272 parameters refined using 0 restraints END WGHT 0.0437 4.7488 REM Highest difference peak 2.124, deepest hole -1.847, 1-sigma level 0.170 Q1 1 0.4509 0.5813 0.0673 11.00000 0.05 2.12 Q2 1 0.4496 0.5125 0.2015 11.00000 0.05 1.94 Q3 1 0.5062 0.2154 0.1389 11.00000 0.05 1.89 Q4 1 0.3931 0.8638 0.1371 11.00000 0.05 1.73 Q5 1 0.4953 0.4507 0.1543 11.00000 0.05 1.67 ; _shelx_res_checksum 98140