# Electronic Supplementary Material (ESI) for ChemComm. # This journal is © The Royal Society of Chemistry 2017 ####################################################################### # # 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_mm524 _database_code_depnum_ccdc_archive 'CCDC 1553992' _audit_update_record ; 2017-06-03 deposited with the CCDC. 2017-07-07 downloaded from the CCDC. ; _audit_creation_method SHELXL-2014/7 _shelx_SHELXL_version_number 2014/7 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H63 Cl7 N16 Ni4 O8.50' _chemical_formula_weight 1314.99 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 2/c' _space_group_name_Hall '-C 2yc' _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+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.7191(4) _cell_length_b 23.4564(7) _cell_length_c 21.6135(7) _cell_angle_alpha 90 _cell_angle_beta 91.4944(14) _cell_angle_gamma 90 _cell_volume 5939.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9922 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 28.30 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_density_meas n/a _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_F_000 2712 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.100 _exptl_absorpt_coefficient_mu 1.619 _shelx_estimated_absorpt_T_min 0.793 _shelx_estimated_absorpt_T_max 0.855 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5723 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS, Bruker (2003)' _exptl_absorpt_special_details ? _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 26465 _diffrn_reflns_av_unetI/netI 0.0205 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.736 _diffrn_reflns_theta_max 28.306 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_point_group_measured_fraction_full 0.989 _reflns_number_total 7335 _reflns_number_gt 5410 _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-2014/7 (Sheldrick, 2014)' _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^)+(0.0670P)^2^+6.2894P] 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 7335 _refine_ls_number_parameters 318 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.034 _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 Ni1 Ni 0.62912(2) 0.11905(2) 0.06051(2) 0.02912(10) Uani 1 1 d . . . . . Ni2 Ni 0.38047(2) 0.12221(2) -0.05836(2) 0.02939(10) Uani 1 1 d . . . . . Cl1 Cl 0.50911(5) 0.18269(2) 0.00071(2) 0.03741(14) Uani 1 1 d . . . . . Cl2 Cl 0.73781(5) 0.18696(3) 0.11469(3) 0.04618(16) Uani 1 1 d . . . . . Cl3 Cl 0.27562(5) 0.19340(3) -0.10781(3) 0.04587(16) Uani 1 1 d . . . . . Cl4 Cl 0.5000 0.39615(5) 0.2500 0.0563(3) Uani 1 2 d S T P . . O1 O 0.74795(15) 0.10920(7) -0.00726(8) 0.0401(4) Uani 1 1 d . . . . . O2 O 0.51132(14) 0.11187(7) 0.13005(8) 0.0389(4) Uani 1 1 d . . . . . O3 O 0.49402(14) 0.11174(7) -0.12922(8) 0.0387(4) Uani 1 1 d . . . . . O4 O 0.26417(15) 0.11242(7) 0.01151(8) 0.0421(4) Uani 1 1 d . . . . . O5 O 0.0000 -0.1037(4) -0.2500 0.081(2) Uani 0.5 2 d S T P . . H5B H -0.0728 -0.1108 -0.2320 0.121 Uiso 0.25 1 d R U P . . H5C H 0.0258 -0.0636 -0.2388 0.121 Uiso 0.25 1 d R U P . . N1 N 0.54664(14) 0.05008(8) 0.02166(8) 0.0270(4) Uani 1 1 d . . . . . N2 N 0.45784(14) 0.05135(8) -0.02110(8) 0.0279(4) Uani 1 1 d . . . . . N3 N 0.28679(14) 0.05368(8) -0.10339(8) 0.0300(4) Uani 1 1 d . . . . . N4 N 0.28398(15) -0.04783(8) -0.10481(8) 0.0303(4) Uani 1 1 d . . . . . N5 N 0.88683(18) 0.13946(9) -0.06899(10) 0.0399(5) Uani 1 1 d . . . . . N6 N 0.3811(2) 0.14946(16) 0.19242(11) 0.0792(10) Uani 1 1 d . U . . . N7 N 0.6350(2) 0.13938(13) -0.19097(10) 0.0537(6) Uani 1 1 d . . . . . N8 N 0.11612(18) 0.13838(10) 0.06922(10) 0.0438(5) Uani 1 1 d . . . . . C1 C 0.41842(18) 0.00114(8) -0.03905(10) 0.0263(4) Uani 1 1 d . . . . . C2 C 0.32358(18) 0.00230(9) -0.08547(10) 0.0280(4) Uani 1 1 d . . . . . C3 C 0.20109(18) 0.05459(11) -0.14556(10) 0.0361(5) Uani 1 1 d . . . . . H3A H 0.1717 0.0901 -0.1598 0.043 Uiso 1 1 calc R U . . . C4 C 0.1548(2) 0.00453(10) -0.16874(12) 0.0402(6) Uani 1 1 d . . . . . H4A H 0.0945 0.0053 -0.1990 0.048 Uiso 1 1 calc R U . . . C5 C 0.19816(19) -0.04672(11) -0.14693(11) 0.0378(5) Uani 1 1 d . . . . . H5A H 0.1667 -0.0815 -0.1620 0.045 Uiso 1 1 calc R U . . . C6 C 0.80190(19) 0.14802(10) -0.03175(10) 0.0352(5) Uani 1 1 d . . . . . H6A H 0.7807 0.1862 -0.0231 0.042 Uiso 1 1 calc R U . . . C7 C 0.9239(3) 0.08216(13) -0.08282(18) 0.0743(11) Uani 1 1 d . . . . . H7A H 0.9877 0.0837 -0.1112 0.111 Uiso 1 1 calc R U . . . H7B H 0.9485 0.0631 -0.0444 0.111 Uiso 1 1 calc R U . . . H7C H 0.8605 0.0609 -0.1022 0.111 Uiso 1 1 calc R U . . . C8 C 0.9531(3) 0.18573(13) -0.09514(15) 0.0572(7) Uani 1 1 d . . . . . H8A H 0.9833 0.1737 -0.1349 0.086 Uiso 1 1 calc R U . . . H8B H 1.0165 0.1955 -0.0666 0.086 Uiso 1 1 calc R U . . . H8C H 0.9040 0.2192 -0.1015 0.086 Uiso 1 1 calc R U . . . C9 C 0.4596(3) 0.15264(13) 0.14987(12) 0.0557(8) Uani 1 1 d . U . . . H9A H 0.4769 0.1892 0.1337 0.067 Uiso 1 1 calc R U . . . C10 C 0.3487(3) 0.0959(2) 0.21784(18) 0.0962(14) Uani 1 1 d . U . . . H10A H 0.2897 0.1019 0.2485 0.144 Uiso 1 1 calc R U . . . H10B H 0.3185 0.0712 0.1847 0.144 Uiso 1 1 calc R U . . . H10C H 0.4154 0.0777 0.2378 0.144 Uiso 1 1 calc R U . . . C11 C 0.3260(5) 0.2001(3) 0.2156(2) 0.161(3) Uani 1 1 d . U . . . H11A H 0.2706 0.1892 0.2467 0.242 Uiso 1 1 calc R U . . . H11B H 0.3835 0.2254 0.2344 0.242 Uiso 1 1 calc R U . . . H11C H 0.2865 0.2199 0.1813 0.242 Uiso 1 1 calc R U . . . C12 C 0.5566(2) 0.14889(12) -0.14938(11) 0.0444(6) Uani 1 1 d . . . . . H12A H 0.5482 0.1866 -0.1342 0.053 Uiso 1 1 calc R U . . . C13 C 0.6538(3) 0.08396(17) -0.21584(18) 0.0786(11) Uani 1 1 d . . . . . H13A H 0.7151 0.0857 -0.2458 0.118 Uiso 1 1 calc R U . . . H13B H 0.6756 0.0577 -0.1823 0.118 Uiso 1 1 calc R U . . . H13C H 0.5836 0.0703 -0.2366 0.118 Uiso 1 1 calc R U . . . C14 C 0.7025(4) 0.18539(19) -0.21634(17) 0.0917(14) Uani 1 1 d . . . . . H14A H 0.7556 0.1698 -0.2463 0.137 Uiso 1 1 calc R U . . . H14B H 0.6518 0.2130 -0.2371 0.137 Uiso 1 1 calc R U . . . H14C H 0.7457 0.2043 -0.1828 0.137 Uiso 1 1 calc R U . . . C15 C 0.20354(19) 0.14973(10) 0.03369(11) 0.0359(5) Uani 1 1 d . . . . . H15A H 0.2203 0.1885 0.0249 0.043 Uiso 1 1 calc R U . . . C16 C 0.0434(3) 0.18327(15) 0.09313(18) 0.0701(9) Uani 1 1 d . . . . . H16A H -0.0161 0.1663 0.1183 0.105 Uiso 1 1 calc R U . . . H16B H 0.0895 0.2095 0.1187 0.105 Uiso 1 1 calc R U . . . H16C H 0.0078 0.2043 0.0585 0.105 Uiso 1 1 calc R U . . . C17 C 0.0869(4) 0.08039(14) 0.0834(2) 0.0850(13) Uani 1 1 d . . . . . H17A H 0.0205 0.0799 0.1101 0.128 Uiso 1 1 calc R U . . . H17B H 0.0686 0.0598 0.0450 0.128 Uiso 1 1 calc R U . . . H17C H 0.1516 0.0619 0.1049 0.128 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 Ni1 0.02877(16) 0.03039(17) 0.02849(16) -0.00478(10) 0.00635(11) -0.00145(11) Ni2 0.02974(16) 0.03040(17) 0.02830(16) 0.00374(10) 0.00568(11) 0.00360(11) Cl1 0.0487(3) 0.0284(3) 0.0352(3) -0.0010(2) 0.0020(2) 0.0015(2) Cl2 0.0437(3) 0.0453(3) 0.0497(3) -0.0188(3) 0.0045(3) -0.0082(3) Cl3 0.0481(3) 0.0421(3) 0.0473(3) 0.0138(3) -0.0001(3) 0.0096(3) Cl4 0.0519(5) 0.0749(7) 0.0413(5) 0.000 -0.0104(4) 0.000 O1 0.0433(9) 0.0375(9) 0.0405(9) -0.0070(7) 0.0194(7) -0.0032(7) O2 0.0391(9) 0.0448(10) 0.0333(8) 0.0007(7) 0.0119(7) 0.0027(7) O3 0.0401(9) 0.0416(9) 0.0351(9) -0.0025(7) 0.0137(7) -0.0031(7) O4 0.0426(9) 0.0432(9) 0.0415(9) 0.0077(7) 0.0178(7) 0.0078(7) O5 0.081(5) 0.116(6) 0.045(3) 0.000 -0.010(3) 0.000 N1 0.0261(8) 0.0280(9) 0.0271(9) -0.0005(7) 0.0024(7) 0.0026(7) N2 0.0266(8) 0.0297(9) 0.0274(9) 0.0002(7) 0.0014(7) 0.0019(7) N3 0.0242(8) 0.0367(10) 0.0293(9) 0.0038(7) 0.0051(7) 0.0021(7) N4 0.0266(8) 0.0367(10) 0.0281(9) -0.0043(7) 0.0060(7) -0.0003(7) N5 0.0423(11) 0.0367(11) 0.0414(11) -0.0012(9) 0.0145(9) -0.0001(9) N6 0.0748(19) 0.124(3) 0.0401(14) 0.0207(15) 0.0247(13) 0.0566(17) N7 0.0517(14) 0.0691(17) 0.0411(13) -0.0072(11) 0.0177(10) -0.0190(12) N8 0.0385(11) 0.0394(12) 0.0543(13) 0.0002(10) 0.0185(9) -0.0037(9) C1 0.0233(9) 0.0309(10) 0.0248(10) -0.0006(8) 0.0050(7) 0.0016(7) C2 0.0222(9) 0.0352(11) 0.0269(10) -0.0002(8) 0.0052(7) 0.0026(8) C3 0.0267(10) 0.0484(14) 0.0334(11) 0.0064(10) 0.0019(8) 0.0053(9) C4 0.0306(11) 0.0533(15) 0.0365(13) 0.0004(10) -0.0030(9) 0.0023(10) C5 0.0294(11) 0.0487(14) 0.0352(12) -0.0060(10) 0.0011(9) -0.0039(10) C6 0.0365(11) 0.0331(11) 0.0365(12) -0.0045(9) 0.0089(9) 0.0003(9) C7 0.095(3) 0.0439(17) 0.087(2) 0.0043(16) 0.056(2) 0.0171(16) C8 0.0583(17) 0.0498(16) 0.0647(18) -0.0025(14) 0.0236(14) -0.0148(13) C9 0.0759(19) 0.0573(17) 0.0351(13) 0.0105(12) 0.0215(12) 0.0313(15) C10 0.065(2) 0.162(4) 0.063(2) 0.013(2) 0.0270(18) -0.018(2) C11 0.228(6) 0.190(5) 0.068(3) 0.045(3) 0.072(3) 0.166(5) C12 0.0553(15) 0.0447(14) 0.0336(12) -0.0041(11) 0.0117(11) -0.0109(12) C13 0.071(2) 0.090(3) 0.076(2) -0.018(2) 0.0368(19) 0.0063(19) C14 0.107(3) 0.104(3) 0.066(2) -0.009(2) 0.035(2) -0.059(3) C15 0.0330(11) 0.0336(11) 0.0417(12) 0.0030(10) 0.0099(9) 0.0005(9) C16 0.0580(18) 0.064(2) 0.090(2) -0.0061(18) 0.0324(17) 0.0124(15) C17 0.101(3) 0.0518(19) 0.106(3) 0.0026(19) 0.064(2) -0.0132(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 Ni1 N1 2.0530(17) . ? Ni1 O1 2.0602(16) . ? Ni1 O2 2.0740(16) . ? Ni1 N4 2.1667(19) 5_655 ? Ni1 Cl2 2.3352(6) . ? Ni1 Cl1 2.4044(6) . ? Ni2 N2 2.0481(17) . ? Ni2 O3 2.0695(16) . ? Ni2 O4 2.0731(16) . ? Ni2 N3 2.1635(19) . ? Ni2 Cl3 2.3179(6) . ? Ni2 Cl1 2.4115(6) . ? O1 C6 1.236(3) . ? O2 C9 1.216(3) . ? O3 C12 1.226(3) . ? O4 C15 1.232(3) . ? N1 C1 1.321(3) 5_655 ? N1 N2 1.374(2) . ? N2 C1 1.320(3) . ? N3 C2 1.334(3) . ? N3 C3 1.339(3) . ? N4 C2 1.328(3) . ? N4 C5 1.339(3) . ? N4 Ni1 2.1667(19) 5_655 ? N5 C6 1.312(3) . ? N5 C7 1.446(3) . ? N5 C8 1.457(3) . ? N6 C9 1.320(3) . ? N6 C10 1.428(6) . ? N6 C11 1.448(5) . ? N7 C12 1.321(3) . ? N7 C13 1.426(4) . ? N7 C14 1.454(4) . ? N8 C15 1.323(3) . ? N8 C17 1.438(4) . ? N8 C16 1.458(4) . ? C1 N1 1.321(3) 5_655 ? C1 C2 1.478(3) . ? C3 C4 1.382(3) . ? C4 C5 1.383(3) . ? 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 N1 Ni1 O1 86.59(7) . . ? N1 Ni1 O2 85.25(7) . . ? O1 Ni1 O2 168.85(7) . . ? N1 Ni1 N4 77.52(7) . 5_655 ? O1 Ni1 N4 84.78(7) . 5_655 ? O2 Ni1 N4 86.05(7) . 5_655 ? N1 Ni1 Cl2 170.93(5) . . ? O1 Ni1 Cl2 93.62(5) . . ? O2 Ni1 Cl2 93.25(5) . . ? N4 Ni1 Cl2 93.46(5) 5_655 . ? N1 Ni1 Cl1 90.39(5) . . ? O1 Ni1 Cl1 94.83(5) . . ? O2 Ni1 Cl1 92.80(5) . . ? N4 Ni1 Cl1 167.91(5) 5_655 . ? Cl2 Ni1 Cl1 98.62(2) . . ? N2 Ni2 O3 84.72(7) . . ? N2 Ni2 O4 85.21(7) . . ? O3 Ni2 O4 166.79(7) . . ? N2 Ni2 N3 77.77(7) . . ? O3 Ni2 N3 84.69(7) . . ? O4 Ni2 N3 84.83(7) . . ? N2 Ni2 Cl3 171.85(5) . . ? O3 Ni2 Cl3 95.02(5) . . ? O4 Ni2 Cl3 93.73(5) . . ? N3 Ni2 Cl3 94.08(5) . . ? N2 Ni2 Cl1 90.28(5) . . ? O3 Ni2 Cl1 93.23(5) . . ? O4 Ni2 Cl1 95.35(5) . . ? N3 Ni2 Cl1 168.01(5) . . ? Cl3 Ni2 Cl1 97.86(2) . . ? Ni1 Cl1 Ni2 105.56(2) . . ? C6 O1 Ni1 125.78(15) . . ? C9 O2 Ni1 122.59(18) . . ? C12 O3 Ni2 125.50(17) . . ? C15 O4 Ni2 126.97(16) . . ? C1 N1 N2 115.78(16) 5_655 . ? C1 N1 Ni1 117.47(14) 5_655 . ? N2 N1 Ni1 126.75(12) . . ? C1 N2 N1 115.56(16) . . ? C1 N2 Ni2 117.43(14) . . ? N1 N2 Ni2 127.00(12) . . ? C2 N3 C3 116.3(2) . . ? C2 N3 Ni2 112.60(14) . . ? C3 N3 Ni2 131.09(16) . . ? C2 N4 C5 116.6(2) . . ? C2 N4 Ni1 112.79(14) . 5_655 ? C5 N4 Ni1 130.65(16) . 5_655 ? C6 N5 C7 120.4(2) . . ? C6 N5 C8 123.0(2) . . ? C7 N5 C8 116.5(2) . . ? C9 N6 C10 121.0(3) . . ? C9 N6 C11 121.3(4) . . ? C10 N6 C11 117.6(3) . . ? C12 N7 C13 121.8(3) . . ? C12 N7 C14 121.8(3) . . ? C13 N7 C14 116.3(3) . . ? C15 N8 C17 120.4(2) . . ? C15 N8 C16 121.9(2) . . ? C17 N8 C16 117.6(2) . . ? N2 C1 N1 128.7(2) . 5_655 ? N2 C1 C2 115.75(18) . . ? N1 C1 C2 115.59(18) 5_655 . ? N4 C2 N3 126.9(2) . . ? N4 C2 C1 116.62(18) . . ? N3 C2 C1 116.44(18) . . ? N3 C3 C4 120.9(2) . . ? C3 C4 C5 118.5(2) . . ? N4 C5 C4 120.8(2) . . ? O1 C6 N5 123.7(2) . . ? O2 C9 N6 124.3(3) . . ? O3 C12 N7 123.7(3) . . ? O4 C15 N8 123.1(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 C1 N1 N2 C1 0.4(3) 5_655 . . . ? Ni1 N1 N2 C1 -179.68(13) . . . . ? C1 N1 N2 Ni2 179.55(13) 5_655 . . . ? Ni1 N1 N2 Ni2 -0.5(3) . . . . ? N1 N2 C1 N1 -0.4(4) . . . 5_655 ? Ni2 N2 C1 N1 -179.70(18) . . . 5_655 ? N1 N2 C1 C2 -179.46(17) . . . . ? Ni2 N2 C1 C2 1.3(3) . . . . ? C5 N4 C2 N3 0.2(3) . . . . ? Ni1 N4 C2 N3 -179.09(17) 5_655 . . . ? C5 N4 C2 C1 -179.92(19) . . . . ? Ni1 N4 C2 C1 0.8(2) 5_655 . . . ? C3 N3 C2 N4 -0.3(3) . . . . ? Ni2 N3 C2 N4 -179.67(17) . . . . ? C3 N3 C2 C1 179.83(18) . . . . ? Ni2 N3 C2 C1 0.4(2) . . . . ? N2 C1 C2 N4 178.97(17) . . . . ? N1 C1 C2 N4 -0.2(3) 5_655 . . . ? N2 C1 C2 N3 -1.1(3) . . . . ? N1 C1 C2 N3 179.71(17) 5_655 . . . ? C2 N3 C3 C4 -0.2(3) . . . . ? Ni2 N3 C3 C4 179.09(17) . . . . ? N3 C3 C4 C5 0.6(4) . . . . ? C2 N4 C5 C4 0.3(3) . . . . ? Ni1 N4 C5 C4 179.47(17) 5_655 . . . ? C3 C4 C5 N4 -0.7(4) . . . . ? Ni1 O1 C6 N5 171.09(18) . . . . ? C7 N5 C6 O1 -1.1(4) . . . . ? C8 N5 C6 O1 -177.0(3) . . . . ? Ni1 O2 C9 N6 177.4(2) . . . . ? C10 N6 C9 O2 -1.5(5) . . . . ? C11 N6 C9 O2 177.6(4) . . . . ? Ni2 O3 C12 N7 173.9(2) . . . . ? C13 N7 C12 O3 -0.4(5) . . . . ? C14 N7 C12 O3 176.2(3) . . . . ? Ni2 O4 C15 N8 166.28(18) . . . . ? C17 N8 C15 O4 -0.5(4) . . . . ? C16 N8 C15 O4 -177.9(3) . . . . ? _refine_diff_density_max 0.756 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.079 _shelx_res_file ; mm524.res created by SHELXL-2014/7 TITL mm524 in C2/c CELL 0.71073 11.71910 23.45640 21.61350 90.0000 91.4944 90.0000 ZERR 4.00 0.00040 0.00070 0.00070 0.0000 0.0014 0.0000 LATT 7 SYMM -X, Y, 0.5-Z SFAC C H N O CL NI UNIT 136 252 64 34 28 16 TEMP -73.150 SIZE 0.10 0.12 0.15 L.S. 80 ACTA CONF LIST 0 BOND FMAP 2 PLAN 5 SIMU C9 N6 C10 C11 RIGU C9 N6 C10 C11 OMIT -4 2 10 OMIT 2 0 10 OMIT -1 7 2 OMIT -2 10 4 OMIT -2 2 8 OMIT -4 0 2 OMIT 0 2 2 OMIT -1 1 8 OMIT 0 0 8 OMIT 2 2 0 OMIT 3 5 6 OMIT -4 6 2 OMIT -4 6 8 OMIT -2 2 2 OMIT -2 4 2 OMIT 1 9 10 OMIT -3 9 4 OMIT -1 11 4 OMIT 5 11 4 OMIT -6 8 5 OMIT 0 2 4 OMIT -8 0 8 OMIT -3 11 2 OMIT -7 21 5 OMIT 4 0 4 OMIT -10 8 11 OMIT -2 2 16 OMIT -4 2 2 OMIT -1 9 6 OMIT -4 6 6 OMIT 4 0 6 OMIT -3 1 5 OMIT 0 0 14 OMIT 8 6 0 OMIT -6 2 8 OMIT -2 0 14 OMIT -12 12 1 OMIT -4 4 5 OMIT -3 17 5 OMIT -1 1 6 OMIT 0 6 12 OMIT 0 18 8 OMIT 7 5 25 OMIT -3 11 3 OMIT 3 7 0 OMIT -2 18 4 OMIT 4 4 7 OMIT -6 2 12 OMIT -4 10 2 OMIT 3 21 1 WGHT 0.067000 6.289400 FVAR 0.03681 NI1 6 0.629125 0.119055 0.060508 11.00000 0.02877 0.03039 = 0.02849 -0.00478 0.00635 -0.00145 NI2 6 0.380466 0.122206 -0.058358 11.00000 0.02974 0.03040 = 0.02830 0.00374 0.00568 0.00360 CL1 5 0.509114 0.182688 0.000714 11.00000 0.04868 0.02842 = 0.03519 -0.00105 0.00198 0.00153 CL2 5 0.737813 0.186965 0.114688 11.00000 0.04371 0.04530 = 0.04969 -0.01881 0.00446 -0.00816 CL3 5 0.275624 0.193404 -0.107812 11.00000 0.04808 0.04214 = 0.04732 0.01378 -0.00011 0.00964 CL4 5 0.500000 0.396148 0.250000 10.50000 0.05193 0.07488 = 0.04134 0.00000 -0.01037 0.00000 O1 4 0.747949 0.109195 -0.007260 11.00000 0.04330 0.03755 = 0.04047 -0.00698 0.01943 -0.00315 O2 4 0.511320 0.111870 0.130048 11.00000 0.03905 0.04480 = 0.03334 0.00072 0.01189 0.00269 O3 4 0.494019 0.111739 -0.129218 11.00000 0.04006 0.04157 = 0.03511 -0.00255 0.01372 -0.00312 O4 4 0.264169 0.112420 0.011509 11.00000 0.04257 0.04317 = 0.04150 0.00768 0.01777 0.00781 O5 4 0.000000 -0.103704 -0.250000 10.25000 0.08142 0.11583 = 0.04462 0.00000 -0.01019 0.00000 AFIX 3 H5B 2 -0.072773 -0.110781 -0.232025 10.25000 -1.50000 H5C 2 0.025832 -0.063641 -0.238798 10.25000 -1.50000 AFIX 0 N1 3 0.546645 0.050079 0.021658 11.00000 0.02615 0.02800 = 0.02707 -0.00051 0.00239 0.00258 N2 3 0.457842 0.051351 -0.021102 11.00000 0.02664 0.02969 = 0.02736 0.00025 0.00141 0.00190 N3 3 0.286792 0.053676 -0.103391 11.00000 0.02423 0.03674 = 0.02928 0.00377 0.00514 0.00214 N4 3 0.283981 -0.047829 -0.104815 11.00000 0.02657 0.03666 = 0.02809 -0.00428 0.00597 -0.00026 N5 3 0.886835 0.139464 -0.068991 11.00000 0.04233 0.03667 = 0.04145 -0.00119 0.01452 -0.00014 N6 3 0.381139 0.149456 0.192418 11.00000 0.07484 0.12393 = 0.04007 0.02066 0.02472 0.05658 N7 3 0.634977 0.139378 -0.190967 11.00000 0.05174 0.06910 = 0.04112 -0.00719 0.01773 -0.01903 N8 3 0.116123 0.138381 0.069223 11.00000 0.03854 0.03935 = 0.05429 0.00023 0.01851 -0.00373 C1 1 0.418419 0.001142 -0.039046 11.00000 0.02329 0.03089 = 0.02481 -0.00061 0.00497 0.00163 C2 1 0.323577 0.002298 -0.085470 11.00000 0.02218 0.03521 = 0.02688 -0.00019 0.00522 0.00258 C3 1 0.201094 0.054588 -0.145564 11.00000 0.02666 0.04840 = 0.03339 0.00644 0.00193 0.00526 AFIX 43 H3A 2 0.171710 0.090138 -0.159757 11.00000 -1.20000 AFIX 0 C4 1 0.154771 0.004526 -0.168744 11.00000 0.03056 0.05326 = 0.03649 0.00045 -0.00301 0.00228 AFIX 43 H4A 2 0.094485 0.005296 -0.198982 11.00000 -1.20000 AFIX 0 C5 1 0.198157 -0.046716 -0.146928 11.00000 0.02943 0.04875 = 0.03520 -0.00597 0.00115 -0.00385 AFIX 43 H5A 2 0.166699 -0.081528 -0.161997 11.00000 -1.20000 AFIX 0 C6 1 0.801898 0.148019 -0.031749 11.00000 0.03653 0.03313 = 0.03648 -0.00452 0.00885 0.00034 AFIX 43 H6A 2 0.780663 0.186230 -0.023118 11.00000 -1.20000 AFIX 0 C7 1 0.923889 0.082164 -0.082822 11.00000 0.09489 0.04393 = 0.08699 0.00432 0.05618 0.01708 AFIX 33 H7A 2 0.987729 0.083701 -0.111173 11.00000 -1.50000 H7B 2 0.948538 0.063063 -0.044425 11.00000 -1.50000 H7C 2 0.860512 0.060897 -0.102242 11.00000 -1.50000 AFIX 0 C8 1 0.953093 0.185731 -0.095138 11.00000 0.05826 0.04981 = 0.06470 -0.00247 0.02361 -0.01477 AFIX 137 H8A 2 0.983312 0.173654 -0.134908 11.00000 -1.50000 H8B 2 1.016516 0.195491 -0.066638 11.00000 -1.50000 H8C 2 0.904016 0.219166 -0.101453 11.00000 -1.50000 AFIX 0 C9 1 0.459622 0.152642 0.149871 11.00000 0.07588 0.05726 = 0.03510 0.01052 0.02150 0.03128 AFIX 43 H9A 2 0.476872 0.189195 0.133658 11.00000 -1.20000 AFIX 0 C10 1 0.348661 0.095862 0.217842 11.00000 0.06483 0.16237 = 0.06282 0.01338 0.02698 -0.01783 AFIX 33 H10A 2 0.289742 0.101876 0.248527 11.00000 -1.50000 H10B 2 0.318543 0.071176 0.184680 11.00000 -1.50000 H10C 2 0.415405 0.077742 0.237772 11.00000 -1.50000 AFIX 0 C11 1 0.325990 0.200080 0.215584 11.00000 0.22827 0.19024 = 0.06845 0.04484 0.07169 0.16598 AFIX 33 H11A 2 0.270642 0.189210 0.246687 11.00000 -1.50000 H11B 2 0.383527 0.225449 0.234432 11.00000 -1.50000 H11C 2 0.286463 0.219853 0.181314 11.00000 -1.50000 AFIX 0 C12 1 0.556583 0.148889 -0.149376 11.00000 0.05526 0.04470 = 0.03365 -0.00413 0.01165 -0.01085 AFIX 43 H12A 2 0.548207 0.186638 -0.134230 11.00000 -1.20000 AFIX 0 C13 1 0.653771 0.083965 -0.215839 11.00000 0.07129 0.09022 = 0.07601 -0.01756 0.03678 0.00634 AFIX 33 H13A 2 0.715059 0.085736 -0.245773 11.00000 -1.50000 H13B 2 0.675615 0.057731 -0.182287 11.00000 -1.50000 H13C 2 0.583556 0.070343 -0.236553 11.00000 -1.50000 AFIX 0 C14 1 0.702523 0.185391 -0.216340 11.00000 0.10675 0.10353 = 0.06637 -0.00910 0.03450 -0.05936 AFIX 33 H14A 2 0.755619 0.169806 -0.246274 11.00000 -1.50000 H14B 2 0.651774 0.213024 -0.237054 11.00000 -1.50000 H14C 2 0.745695 0.204350 -0.182791 11.00000 -1.50000 AFIX 0 C15 1 0.203539 0.149732 0.033689 11.00000 0.03300 0.03358 = 0.04168 0.00299 0.00991 0.00053 AFIX 43 H15A 2 0.220339 0.188464 0.024866 11.00000 -1.20000 AFIX 0 C16 1 0.043363 0.183273 0.093134 11.00000 0.05804 0.06373 = 0.09024 -0.00612 0.03240 0.01239 AFIX 33 H16A 2 -0.016114 0.166253 0.118281 11.00000 -1.50000 H16B 2 0.089548 0.209483 0.118689 11.00000 -1.50000 H16C 2 0.007752 0.204257 0.058502 11.00000 -1.50000 AFIX 0 C17 1 0.086896 0.080387 0.083443 11.00000 0.10055 0.05178 = 0.10603 0.00263 0.06448 -0.01323 AFIX 33 H17A 2 0.020500 0.079920 0.110080 11.00000 -1.50000 H17B 2 0.068630 0.059782 0.045003 11.00000 -1.50000 H17C 2 0.151638 0.061935 0.104936 11.00000 -1.50000 AFIX 0 HKLF 4 REM mm524 in C2/c REM R1 = 0.0406 for 5410 Fo > 4sig(Fo) and 0.0586 for all 7335 data REM 318 parameters refined using 36 restraints END WGHT 0.0668 6.4795 REM Highest difference peak 0.756, deepest hole -0.496, 1-sigma level 0.079 Q1 1 0.6775 0.2049 0.1146 11.00000 0.05 0.49 Q2 1 0.5034 0.0535 -0.0018 11.00000 0.05 0.42 Q3 1 0.0534 0.1773 0.1380 11.00000 0.05 0.40 Q4 1 0.3702 -0.0015 -0.0586 11.00000 0.05 0.37 Q5 1 0.6407 0.2195 -0.2162 11.00000 0.05 0.36 ; _shelx_res_checksum 87700