# Electronic Supplementary Material (ESI) for Dalton Transactions. # This journal is © The Royal Society of Chemistry 2015 ####################################################################### # # 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_mm399 _database_code_depnum_ccdc_archive 'CCDC 1048781' _audit_update_record ; 2015-02-10 deposited with the CCDC. 2015-10-19 downloaded from the CCDC. ; _audit_creation_method SHELXL-2013 _chemical_name_systematic Gd-EDTA _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H28 Gd N2 Na O16' _chemical_formula_weight 612.58 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' Na Na 0.0362 0.0249 '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 9 _space_group_name_H-M_alt 'C 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' _cell_length_a 12.0641(4) _cell_length_b 19.3270(6) _cell_length_c 18.6758(6) _cell_angle_alpha 90 _cell_angle_beta 108.7327(13) _cell_angle_gamma 90 _cell_volume 4123.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9158 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 28.34 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_density_meas n/a _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.973 _exptl_crystal_F_000 2440 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.190 _exptl_crystal_size_min 0.160 _exptl_absorpt_coefficient_mu 3.319 _shelx_estimated_absorpt_T_min 0.503 _shelx_estimated_absorpt_T_max 0.619 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6143 _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 29817 _diffrn_reflns_av_unetI/netI 0.0267 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.071 _diffrn_reflns_theta_max 28.344 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.959 _diffrn_reflns_point_group_measured_fraction_full 0.956 _reflns_number_total 9608 _reflns_number_gt 9577 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.918 _reflns_Friedel_fraction_max 0.919 _reflns_Friedel_fraction_full 0.915 _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 ; 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^)+(0.0371P)^2^+7.0108P] 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_abs_structure_details ; Flack x determined using 4416 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.577(4) _chemical_absolute_configuration ? _refine_ls_number_reflns 9608 _refine_ls_number_parameters 542 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0217 _refine_ls_R_factor_gt 0.0216 _refine_ls_wR_factor_ref 0.0577 _refine_ls_wR_factor_gt 0.0576 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Gd1 Gd 0.06729(3) 0.54123(2) 0.72037(2) 0.00912(12) Uani 1 1 d . . . . . Gd2 Gd 0.38201(2) 0.29342(2) 0.84122(2) 0.00909(12) Uani 1 1 d . . . . . Na1 Na 0.3985(4) 0.4830(2) 0.7588(3) 0.0220(9) Uani 1 1 d . . . . . Na2 Na 0.6703(4) 0.2412(2) 0.7913(3) 0.0254(10) Uani 1 1 d . . . . . O1 O -0.1068(6) 0.6067(3) 0.7023(4) 0.0127(14) Uani 1 1 d . . . . . O2 O -0.2959(7) 0.6155(4) 0.6905(6) 0.0246(19) Uani 1 1 d . . . . . O3 O 0.0854(6) 0.4198(3) 0.6918(4) 0.0136(13) Uani 1 1 d . . . . . O4 O 0.0199(7) 0.3116(4) 0.6792(6) 0.0261(18) Uani 1 1 d . . . . . O5 O 0.1276(7) 0.6531(4) 0.6915(5) 0.0176(14) Uani 1 1 d . . . . . O6 O 0.1666(8) 0.7238(5) 0.6083(6) 0.036(2) Uani 1 1 d . . . . . O7 O 0.2212(6) 0.5267(4) 0.6638(5) 0.0145(13) Uani 1 1 d . . . . . O8 O 0.2822(7) 0.5176(6) 0.5628(5) 0.032(2) Uani 1 1 d . . . . . O9 O -0.0100(7) 0.4879(4) 0.8111(5) 0.0183(16) Uani 1 1 d . . . . . H9C H 0.0402 0.4532 0.8410 0.027 Uiso 1 1 d R U . . . H9D H -0.0491 0.5147 0.8425 0.027 Uiso 1 1 d R U . . . O10 O 0.2392(6) 0.4935(3) 0.8160(4) 0.0131(14) Uani 1 1 d . . . . . H10A H 0.2331 0.4452 0.8251 0.020 Uiso 1 1 d R U . . . H10B H 0.2772 0.5186 0.8649 0.020 Uiso 1 1 d R U . . . O11 O 0.1141(6) 0.6224(3) 0.8317(5) 0.0153(14) Uani 1 1 d . . . . . H11C H 0.0483 0.6419 0.8425 0.023 Uiso 1 1 d R U . . . H11D H 0.1692 0.6008 0.8786 0.023 Uiso 1 1 d R U . . . O12 O 0.4291(7) 0.1730(4) 0.8697(5) 0.0196(16) Uani 1 1 d . . . . . O13 O 0.3818(7) 0.0651(4) 0.8897(6) 0.0241(16) Uani 1 1 d . . . . . O14 O 0.2261(6) 0.3584(4) 0.8590(5) 0.0167(16) Uani 1 1 d . . . . . O15 O 0.0483(8) 0.3640(4) 0.8727(6) 0.0234(18) Uani 1 1 d . . . . . O16 O 0.5918(7) 0.2806(4) 0.8938(5) 0.0173(15) Uani 1 1 d . . . . . O17 O 0.7538(7) 0.2722(5) 0.9907(5) 0.0242(17) Uani 1 1 d . . . . . O18 O 0.4645(6) 0.4052(4) 0.8632(5) 0.0173(14) Uani 1 1 d . . . . . O19 O 0.5860(9) 0.4771(6) 0.9429(6) 0.040(2) Uani 1 1 d . . . . . O20 O 0.2115(7) 0.2390(4) 0.7541(5) 0.0189(16) Uani 1 1 d . . . . . H20A H 0.2216 0.2009 0.7241 0.028 Uiso 1 1 d R U . . . H20B H 0.1448 0.2690 0.7242 0.028 Uiso 1 1 d R U . . . O21 O 0.4519(6) 0.2425(3) 0.7418(5) 0.0157(15) Uani 1 1 d . . . . . H21A H 0.4259 0.1960 0.7289 0.023 Uiso 1 1 d R U . . . H21B H 0.4412 0.2706 0.6948 0.023 Uiso 1 1 d R U . . . O22 O 0.3064(6) 0.3698(3) 0.7246(6) 0.0154(12) Uani 1 1 d . . . . . H22A H 0.2265 0.3841 0.7095 0.023 Uiso 1 1 d R U . . . H22B H 0.3273 0.3523 0.6798 0.023 Uiso 1 1 d R U . . . O23 O 0.4913(10) 0.4878(8) 0.6644(8) 0.076(4) Uani 1 1 d . . . . . H23A H 0.5182 0.5344 0.6646 0.114 Uiso 1 1 d R U . . . H23B H 0.5372 0.4559 0.6420 0.114 Uiso 1 1 d R U . . . O24 O 0.4816(10) 0.5918(5) 0.7892(8) 0.075(4) Uani 1 1 d . . . . . H24A H 0.5451 0.5872 0.8353 0.112 Uiso 1 1 d R U . . . H24B H 0.4798 0.6398 0.7682 0.112 Uiso 1 1 d R U . . . O25 O 0.6548(11) 0.3562(4) 0.7486(5) 0.052(2) Uani 1 1 d . . . . . H25A H 0.6222 0.3694 0.6967 0.079 Uiso 1 1 d R U . . . H25B H 0.6589 0.3973 0.7824 0.079 Uiso 1 1 d R U . . . O26 O 0.8589(7) 0.2605(5) 0.8848(5) 0.0315(17) Uani 1 1 d . . . . . H26A H 0.8258 0.2770 0.9218 0.047 Uiso 1 1 d R U . . . H26B H 0.9418 0.2770 0.8969 0.047 Uiso 1 1 d R U . . . O27 O 0.5764(8) 0.3563(5) 0.5817(6) 0.050(2) Uani 1 1 d . . . . . H27A H 0.5776 0.3498 0.5260 0.075 Uiso 1 1 d R U . . . H27B H 0.6132 0.3126 0.6079 0.075 Uiso 1 1 d R U . . . O28 O -0.1123(12) 0.2138(5) 0.7251(8) 0.056(3) Uani 1 1 d . . . . . H28A H -0.1849 0.2243 0.6873 0.085 Uiso 1 1 d R U . . . H28B H -0.0603 0.2557 0.7363 0.085 Uiso 1 1 d R U . . . O29 O 0.8715(7) 0.1879(4) 1.1094(5) 0.0272(17) Uani 1 1 d . . . . . H29A H 0.8240 0.2138 1.0671 0.041 Uiso 1 1 d R U . . . H29B H 0.9352 0.1631 1.0957 0.041 Uiso 1 1 d R U . . . O30 O 0.1771(11) -0.0142(6) 0.8274(7) 0.052(3) Uani 1 1 d . . . . . H30A H 0.2469 0.0127 0.8376 0.078 Uiso 1 1 d R U . . . H30B H 0.1532 -0.0182 0.8742 0.078 Uiso 1 1 d R U . . . O31 O 0.2834(7) 0.5615(4) 0.9459(5) 0.0234(16) Uani 1 1 d . . . . . H31A H 0.2794 0.5352 0.9885 0.035 Uiso 1 1 d R U . . . H31B H 0.3619 0.5844 0.9576 0.035 Uiso 1 1 d R U . . . O32 O 0.4674(7) 0.6338(4) 0.9312(6) 0.0451(18) Uani 1 1 d . . . . . H32A H 0.4266 0.6767 0.9174 0.068 Uiso 1 1 d R U . . . H32B H 0.5038 0.6196 0.8919 0.068 Uiso 1 1 d R U . . . N1 N -0.1299(8) 0.4744(5) 0.6462(6) 0.0137(16) Uani 1 1 d . . . . . N2 N 0.0006(7) 0.5671(4) 0.5734(5) 0.0152(17) Uani 1 1 d . . . . . N3 N 0.2651(8) 0.2276(5) 0.9209(6) 0.0134(17) Uani 1 1 d . . . . . N4 N 0.4617(7) 0.3231(4) 0.9854(5) 0.0145(16) Uani 1 1 d . . . . . C1 C -0.1463(8) 0.4755(5) 0.5641(6) 0.0167(18) Uani 1 1 d . . . . . H1A H -0.0931 0.4412 0.5530 0.020 Uiso 1 1 calc R U . . . H1B H -0.2276 0.4615 0.5359 0.020 Uiso 1 1 calc R U . . . C2 C -0.1231(10) 0.5448(5) 0.5370(8) 0.019(2) Uani 1 1 d . . . . . H2A H -0.1761 0.5792 0.5482 0.023 Uiso 1 1 calc R U . . . H2B H -0.1405 0.5433 0.4815 0.023 Uiso 1 1 calc R U . . . C3 C -0.2274(9) 0.5080(5) 0.6632(7) 0.017(2) Uani 1 1 d . . . . . H3A H -0.2445 0.4816 0.7039 0.021 Uiso 1 1 calc R U . . . H3B H -0.2976 0.5054 0.6177 0.021 Uiso 1 1 calc R U . . . C4 C -0.2070(8) 0.5823(5) 0.6873(6) 0.0129(18) Uani 1 1 d . . . . . C5 C -0.1169(9) 0.4016(5) 0.6722(7) 0.017(2) Uani 1 1 d . . . . . H5A H -0.1750 0.3725 0.6348 0.021 Uiso 1 1 calc R U . . . H5B H -0.1327 0.3982 0.7209 0.021 Uiso 1 1 calc R U . . . C6 C 0.0052(8) 0.3750(4) 0.6819(6) 0.0137(18) Uani 1 1 d . . . . . C7 C 0.0121(10) 0.6422(5) 0.5631(6) 0.0193(19) Uani 1 1 d . . . . . H7A H -0.0621 0.6652 0.5612 0.023 Uiso 1 1 calc R U . . . H7B H 0.0251 0.6503 0.5140 0.023 Uiso 1 1 calc R U . . . C8 C 0.1122(9) 0.6746(5) 0.6260(7) 0.018(2) Uani 1 1 d . . . . . C9 C 0.0794(12) 0.5298(8) 0.5409(9) 0.025(3) Uani 1 1 d . . . . . H9A H 0.0780 0.5530 0.4934 0.030 Uiso 1 1 calc R U . . . H9B H 0.0493 0.4822 0.5280 0.030 Uiso 1 1 calc R U . . . C10 C 0.2038(8) 0.5258(5) 0.5922(7) 0.0151(17) Uani 1 1 d . . . . . C11 C 0.3316(9) 0.2311(5) 1.0019(6) 0.0181(19) Uani 1 1 d . . . . . H11A H 0.3962 0.1971 1.0134 0.022 Uiso 1 1 calc R U . . . H11B H 0.2795 0.2180 1.0312 0.022 Uiso 1 1 calc R U . . . C12 C 0.3817(10) 0.3014(5) 1.0270(7) 0.014(2) Uani 1 1 d . . . . . H12A H 0.3173 0.3354 1.0181 0.017 Uiso 1 1 calc R U . . . H12B H 0.4250 0.3004 1.0819 0.017 Uiso 1 1 calc R U . . . C13 C 0.2529(9) 0.1547(5) 0.8974(6) 0.0131(17) Uani 1 1 d . . . . . H13A H 0.1876 0.1500 0.8494 0.016 Uiso 1 1 calc R U . . . H13B H 0.2341 0.1265 0.9363 0.016 Uiso 1 1 calc R U . . . C14 C 0.3645(9) 0.1281(5) 0.8868(7) 0.016(2) Uani 1 1 d . . . . . C15 C 0.1474(10) 0.2586(5) 0.9055(7) 0.019(2) Uani 1 1 d . . . . . H15A H 0.1259 0.2569 0.9523 0.022 Uiso 1 1 calc R U . . . H15B H 0.0898 0.2303 0.8669 0.022 Uiso 1 1 calc R U . . . C16 C 0.1391(10) 0.3338(5) 0.8776(6) 0.0162(19) Uani 1 1 d . . . . . C17 C 0.5770(12) 0.2859(6) 1.0182(9) 0.020(3) Uani 1 1 d . . . . . H17A H 0.5620 0.2389 1.0341 0.024 Uiso 1 1 calc R U . . . H17B H 0.6253 0.3110 1.0637 0.024 Uiso 1 1 calc R U . . . C18 C 0.6457(8) 0.2799(5) 0.9620(7) 0.0162(19) Uani 1 1 d . . . . . C19 C 0.4812(11) 0.3984(5) 0.9926(7) 0.024(2) Uani 1 1 d . . . . . H19A H 0.5434 0.4081 1.0410 0.029 Uiso 1 1 calc R U . . . H19B H 0.4086 0.4211 0.9945 0.029 Uiso 1 1 calc R U . . . C20 C 0.5158(9) 0.4297(5) 0.9291(7) 0.020(2) Uani 1 1 d . . . . . 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 0.0082(3) 0.00912(18) 0.0095(2) 0.00002(14) 0.00203(19) 0.00082(15) Gd2 0.0075(3) 0.00908(18) 0.0100(3) 0.00016(14) 0.00187(19) 0.00093(15) Na1 0.0224(19) 0.0207(18) 0.022(2) 0.0044(14) 0.0064(16) 0.0005(14) Na2 0.023(2) 0.026(2) 0.023(2) -0.0046(16) 0.0025(17) -0.0009(15) O1 0.010(3) 0.013(3) 0.014(4) 0.001(3) 0.003(3) 0.002(2) O2 0.013(4) 0.019(3) 0.039(6) -0.006(3) 0.005(4) 0.007(3) O3 0.013(3) 0.011(3) 0.015(3) -0.002(2) 0.002(3) 0.003(2) O4 0.016(3) 0.011(3) 0.043(5) -0.002(3) -0.003(3) 0.000(3) O5 0.025(3) 0.014(3) 0.016(3) -0.003(2) 0.009(3) -0.003(3) O6 0.034(4) 0.040(4) 0.033(5) 0.015(4) 0.009(4) -0.015(4) O7 0.008(3) 0.022(3) 0.013(4) 0.000(3) 0.003(3) 0.000(3) O8 0.017(3) 0.062(6) 0.017(4) -0.008(4) 0.007(3) 0.006(3) O9 0.027(4) 0.015(3) 0.017(4) 0.003(3) 0.013(3) 0.010(3) O10 0.013(3) 0.014(3) 0.011(3) -0.001(2) 0.003(3) 0.002(2) O11 0.016(3) 0.018(2) 0.012(4) 0.001(2) 0.005(3) 0.005(2) O12 0.015(3) 0.016(3) 0.033(5) 0.005(3) 0.015(3) 0.001(2) O13 0.025(3) 0.012(3) 0.043(5) 0.004(3) 0.022(3) 0.007(3) O14 0.015(3) 0.011(3) 0.027(5) 0.004(3) 0.012(3) 0.002(2) O15 0.020(4) 0.019(3) 0.036(5) 0.009(3) 0.016(4) 0.009(3) O16 0.016(3) 0.021(3) 0.012(4) -0.002(3) 0.001(3) 0.004(3) O17 0.011(3) 0.042(4) 0.017(4) 0.006(3) 0.001(3) 0.002(3) O18 0.014(3) 0.018(3) 0.019(4) -0.002(3) 0.003(3) -0.004(2) O19 0.045(5) 0.045(5) 0.029(5) -0.012(4) 0.011(4) -0.028(4) O20 0.015(3) 0.014(3) 0.025(4) -0.003(3) 0.003(3) -0.002(3) O21 0.019(4) 0.012(3) 0.017(4) -0.003(2) 0.007(3) 0.002(3) O22 0.015(3) 0.016(2) 0.015(4) 0.002(2) 0.004(3) 0.005(2) O23 0.039(6) 0.133(12) 0.060(8) 0.021(8) 0.023(5) 0.029(7) O24 0.059(6) 0.041(5) 0.097(10) -0.011(5) -0.014(6) -0.018(5) O25 0.093(8) 0.034(4) 0.032(4) 0.004(3) 0.023(5) -0.006(4) O26 0.021(3) 0.045(4) 0.031(4) -0.004(3) 0.012(3) -0.003(3) O27 0.042(4) 0.056(5) 0.053(5) 0.003(4) 0.016(4) 0.000(4) O28 0.071(7) 0.053(6) 0.038(6) 0.008(4) 0.007(5) -0.030(5) O29 0.028(4) 0.038(4) 0.012(4) 0.002(3) 0.002(3) -0.001(3) O30 0.058(6) 0.067(7) 0.033(5) -0.011(5) 0.019(4) -0.026(5) O31 0.020(3) 0.025(3) 0.022(4) 0.001(3) 0.001(3) -0.005(3) O32 0.039(4) 0.035(4) 0.061(5) 0.005(4) 0.016(4) -0.005(3) N1 0.010(4) 0.019(4) 0.011(4) -0.002(3) 0.001(3) 0.001(3) N2 0.017(4) 0.011(3) 0.015(4) 0.000(3) 0.002(3) 0.000(3) N3 0.013(4) 0.004(3) 0.025(5) 0.001(3) 0.009(3) 0.005(3) N4 0.008(3) 0.023(4) 0.012(4) 0.001(3) 0.003(3) 0.006(3) C1 0.013(4) 0.013(4) 0.021(5) -0.003(3) 0.000(4) -0.002(3) C2 0.010(5) 0.029(6) 0.013(5) 0.002(4) -0.005(4) -0.003(3) C3 0.007(4) 0.019(4) 0.026(5) -0.007(3) 0.005(4) 0.001(3) C4 0.007(4) 0.014(4) 0.015(5) -0.001(3) -0.001(3) 0.007(3) C5 0.011(4) 0.008(4) 0.036(6) 0.002(3) 0.012(4) 0.001(3) C6 0.009(4) 0.013(4) 0.016(4) -0.001(3) -0.001(3) 0.002(3) C7 0.017(4) 0.023(4) 0.012(4) 0.006(3) -0.003(4) 0.000(4) C8 0.016(4) 0.014(4) 0.026(6) 0.006(3) 0.010(4) 0.003(3) C9 0.016(5) 0.044(6) 0.015(6) -0.005(5) 0.006(4) 0.003(5) C10 0.015(4) 0.018(4) 0.014(5) -0.003(3) 0.008(3) 0.001(3) C11 0.020(4) 0.024(5) 0.013(4) 0.007(4) 0.009(4) 0.006(4) C12 0.011(4) 0.016(4) 0.015(5) 0.000(3) 0.002(4) 0.004(3) C13 0.015(4) 0.012(4) 0.015(4) 0.003(3) 0.007(3) 0.001(3) C14 0.018(4) 0.016(4) 0.015(4) 0.003(3) 0.006(3) 0.004(3) C15 0.020(5) 0.012(4) 0.028(5) 0.006(3) 0.013(4) 0.004(3) C16 0.021(5) 0.013(4) 0.013(4) 0.000(3) 0.004(4) -0.003(4) C17 0.015(5) 0.029(6) 0.013(6) 0.005(4) 0.003(4) 0.010(4) C18 0.018(4) 0.020(4) 0.013(5) 0.005(4) 0.007(4) 0.000(3) C19 0.028(5) 0.019(4) 0.023(5) -0.008(4) 0.005(4) -0.007(4) C20 0.015(4) 0.019(4) 0.021(5) -0.003(3) 0.000(4) -0.002(3) _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 2.381(6) . ? Gd1 O5 2.397(7) . ? Gd1 O9 2.411(8) . ? Gd1 O7 2.430(7) . ? Gd1 O3 2.432(6) . ? Gd1 O10 2.442(7) . ? Gd1 O11 2.520(8) . ? Gd1 N2 2.649(10) . ? Gd1 N1 2.670(9) . ? Gd1 Na1 3.988(5) . ? Gd1 Na2 4.144(4) 3_455 ? Gd2 O18 2.358(7) . ? Gd2 O14 2.372(7) . ? Gd2 O20 2.415(8) . ? Gd2 O12 2.414(7) . ? Gd2 O16 2.416(8) . ? Gd2 O21 2.476(7) . ? Gd2 O22 2.545(9) . ? Gd2 N4 2.616(9) . ? Gd2 N3 2.678(10) . ? Gd2 Na1 4.004(4) . ? Gd2 Na2 4.008(5) . ? Na1 O24 2.320(10) . ? Na1 O23 2.374(14) . ? Na1 O18 2.388(9) . ? Na1 O22 2.444(8) . ? Na1 O7 2.450(9) . ? Na1 O10 2.489(9) . ? Na2 O25 2.349(9) . ? Na2 O26 2.410(10) . ? Na2 O5 2.454(9) 3_545 ? Na2 O21 2.497(9) . ? Na2 O16 2.510(10) . ? Na2 O11 2.575(8) 3_545 ? Na2 Gd1 4.144(4) 3_545 ? O1 C4 1.243(12) . ? O2 C4 1.266(12) . ? O3 C6 1.268(11) . ? O4 C6 1.242(11) . ? O5 C8 1.249(14) . ? O5 Na2 2.454(9) 3_455 ? O6 C8 1.259(13) . ? O7 C10 1.285(14) . ? O8 C10 1.246(13) . ? O11 Na2 2.575(8) 3_455 ? O12 C14 1.273(12) . ? O13 C14 1.235(11) . ? O14 C16 1.296(13) . ? O15 C16 1.219(14) . ? O16 C18 1.231(15) . ? O17 C18 1.249(13) . ? O18 C20 1.278(15) . ? O19 C20 1.219(14) . ? N1 C3 1.465(13) . ? N1 C5 1.479(13) . ? N1 C1 1.483(15) . ? N2 C9 1.470(15) . ? N2 C7 1.475(12) . ? N2 C2 1.492(14) . ? N3 C11 1.469(15) . ? N3 C13 1.468(12) . ? N3 C15 1.482(13) . ? N4 C19 1.473(11) . ? N4 C12 1.480(14) . ? N4 C17 1.510(14) . ? C1 C2 1.490(14) . ? C3 C4 1.502(14) . ? C5 C6 1.516(13) . ? C7 C8 1.524(15) . ? C9 C10 1.501(17) . ? C11 C12 1.498(15) . ? C13 C14 1.512(14) . ? C15 C16 1.536(13) . ? C17 C18 1.536(17) . ? C19 C20 1.504(17) . ? 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 O5 78.9(3) . . ? O1 Gd1 O9 78.7(3) . . ? O5 Gd1 O9 139.2(3) . . ? O1 Gd1 O7 139.7(3) . . ? O5 Gd1 O7 71.1(3) . . ? O9 Gd1 O7 141.1(3) . . ? O1 Gd1 O3 128.2(2) . . ? O5 Gd1 O3 139.9(3) . . ? O9 Gd1 O3 79.9(3) . . ? O7 Gd1 O3 70.0(3) . . ? O1 Gd1 O10 143.8(2) . . ? O5 Gd1 O10 104.9(3) . . ? O9 Gd1 O10 75.7(3) . . ? O7 Gd1 O10 71.7(3) . . ? O3 Gd1 O10 71.4(2) . . ? O1 Gd1 O11 74.9(2) . . ? O5 Gd1 O11 67.7(3) . . ? O9 Gd1 O11 73.8(3) . . ? O7 Gd1 O11 115.5(3) . . ? O3 Gd1 O11 140.3(2) . . ? O10 Gd1 O11 73.7(2) . . ? O1 Gd1 N2 78.0(3) . . ? O5 Gd1 N2 67.0(3) . . ? O9 Gd1 N2 138.7(3) . . ? O7 Gd1 N2 65.8(3) . . ? O3 Gd1 N2 88.5(2) . . ? O10 Gd1 N2 137.2(3) . . ? O11 Gd1 N2 130.6(2) . . ? O1 Gd1 N1 65.5(3) . . ? O5 Gd1 N1 127.2(3) . . ? O9 Gd1 N1 71.1(3) . . ? O7 Gd1 N1 113.3(3) . . ? O3 Gd1 N1 63.1(3) . . ? O10 Gd1 N1 127.0(3) . . ? O11 Gd1 N1 130.9(3) . . ? N2 Gd1 N1 68.3(3) . . ? O1 Gd1 Na1 164.26(18) . . ? O5 Gd1 Na1 86.3(2) . . ? O9 Gd1 Na1 110.1(2) . . ? O7 Gd1 Na1 35.4(2) . . ? O3 Gd1 Na1 67.15(18) . . ? O10 Gd1 Na1 36.43(18) . . ? O11 Gd1 Na1 94.65(18) . . ? N2 Gd1 Na1 101.1(2) . . ? N1 Gd1 Na1 129.1(2) . . ? O1 Gd1 Na2 73.15(18) . 3_455 ? O5 Gd1 Na2 31.7(2) . 3_455 ? O9 Gd1 Na2 108.5(2) . 3_455 ? O7 Gd1 Na2 93.1(2) . 3_455 ? O3 Gd1 Na2 158.59(18) . 3_455 ? O10 Gd1 Na2 91.20(18) . 3_455 ? O11 Gd1 Na2 36.01(18) . 3_455 ? N2 Gd1 Na2 96.62(17) . 3_455 ? N1 Gd1 Na2 138.0(2) . 3_455 ? Na1 Gd1 Na2 91.44(9) . 3_455 ? O18 Gd2 O14 78.5(3) . . ? O18 Gd2 O20 137.4(3) . . ? O14 Gd2 O20 77.4(3) . . ? O18 Gd2 O12 142.0(3) . . ? O14 Gd2 O12 128.3(2) . . ? O20 Gd2 O12 79.5(3) . . ? O18 Gd2 O16 72.2(3) . . ? O14 Gd2 O16 140.5(3) . . ? O20 Gd2 O16 141.6(3) . . ? O12 Gd2 O16 70.7(3) . . ? O18 Gd2 O21 105.6(3) . . ? O14 Gd2 O21 142.4(3) . . ? O20 Gd2 O21 75.1(3) . . ? O12 Gd2 O21 70.7(3) . . ? O16 Gd2 O21 72.5(3) . . ? O18 Gd2 O22 68.5(3) . . ? O14 Gd2 O22 74.4(3) . . ? O20 Gd2 O22 71.5(3) . . ? O12 Gd2 O22 137.9(3) . . ? O16 Gd2 O22 116.6(3) . . ? O21 Gd2 O22 72.8(2) . . ? O18 Gd2 N4 67.9(3) . . ? O14 Gd2 N4 77.6(3) . . ? O20 Gd2 N4 137.8(3) . . ? O12 Gd2 N4 90.1(3) . . ? O16 Gd2 N4 67.3(3) . . ? O21 Gd2 N4 139.3(3) . . ? O22 Gd2 N4 131.7(2) . . ? O18 Gd2 N3 127.3(3) . . ? O14 Gd2 N3 65.8(3) . . ? O20 Gd2 N3 71.4(3) . . ? O12 Gd2 N3 63.1(3) . . ? O16 Gd2 N3 113.3(3) . . ? O21 Gd2 N3 126.5(3) . . ? O22 Gd2 N3 130.0(3) . . ? N4 Gd2 N3 67.5(3) . . ? O18 Gd2 Na1 32.7(2) . . ? O14 Gd2 Na1 73.10(19) . . ? O20 Gd2 Na1 106.0(2) . . ? O12 Gd2 Na1 158.4(2) . . ? O16 Gd2 Na1 94.3(2) . . ? O21 Gd2 Na1 90.27(18) . . ? O22 Gd2 Na1 35.77(19) . . ? N4 Gd2 Na1 98.49(18) . . ? N3 Gd2 Na1 138.5(2) . . ? O18 Gd2 Na2 85.53(19) . . ? O14 Gd2 Na2 162.25(18) . . ? O20 Gd2 Na2 110.4(2) . . ? O12 Gd2 Na2 69.38(19) . . ? O16 Gd2 Na2 36.3(2) . . ? O21 Gd2 Na2 36.47(19) . . ? O22 Gd2 Na2 92.69(17) . . ? N4 Gd2 Na2 103.60(19) . . ? N3 Gd2 Na2 131.3(2) . . ? Na1 Gd2 Na2 89.27(10) . . ? O24 Na1 O23 82.9(6) . . ? O24 Na1 O18 111.5(4) . . ? O23 Na1 O18 121.2(4) . . ? O24 Na1 O22 178.5(4) . . ? O23 Na1 O22 97.2(5) . . ? O18 Na1 O22 69.7(3) . . ? O24 Na1 O7 94.2(4) . . ? O23 Na1 O7 87.6(4) . . ? O18 Na1 O7 142.5(3) . . ? O22 Na1 O7 84.3(3) . . ? O24 Na1 O10 98.8(4) . . ? O23 Na1 O10 158.2(4) . . ? O18 Na1 O10 78.6(3) . . ? O22 Na1 O10 80.6(3) . . ? O7 Na1 O10 70.6(3) . . ? O24 Na1 Gd1 96.8(3) . . ? O23 Na1 Gd1 122.6(3) . . ? O18 Na1 Gd1 112.1(2) . . ? O22 Na1 Gd1 81.96(19) . . ? O7 Na1 Gd1 35.02(19) . . ? O10 Na1 Gd1 35.63(18) . . ? O24 Na1 Gd2 143.7(4) . . ? O23 Na1 Gd2 114.5(4) . . ? O18 Na1 Gd2 32.25(19) . . ? O22 Na1 Gd2 37.5(2) . . ? O7 Na1 Gd2 117.0(2) . . ? O10 Na1 Gd2 76.65(19) . . ? Gd1 Na1 Gd2 99.02(10) . . ? O25 Na2 O26 93.0(4) . . ? O25 Na2 O5 115.1(4) . 3_545 ? O26 Na2 O5 125.2(4) . 3_545 ? O25 Na2 O21 84.5(4) . . ? O26 Na2 O21 154.8(4) . . ? O5 Na2 O21 77.7(3) 3_545 . ? O25 Na2 O16 87.9(3) . . ? O26 Na2 O16 84.3(3) . . ? O5 Na2 O16 138.7(3) 3_545 . ? O21 Na2 O16 70.6(3) . . ? O25 Na2 O11 160.7(4) . 3_545 ? O26 Na2 O11 101.7(3) . 3_545 ? O5 Na2 O11 66.0(3) 3_545 3_545 ? O21 Na2 O11 76.8(3) . 3_545 ? O16 Na2 O11 81.3(3) . 3_545 ? O25 Na2 Gd2 82.0(3) . . ? O26 Na2 Gd2 118.7(3) . . ? O5 Na2 Gd2 111.4(2) 3_545 . ? O21 Na2 Gd2 36.11(19) . . ? O16 Na2 Gd2 34.77(19) . . ? O11 Na2 Gd2 80.01(19) 3_545 . ? O25 Na2 Gd1 142.2(3) . 3_545 ? O26 Na2 Gd1 119.5(3) . 3_545 ? O5 Na2 Gd1 30.90(19) 3_545 3_545 ? O21 Na2 Gd1 73.66(18) . 3_545 ? O16 Na2 Gd1 112.3(2) . 3_545 ? O11 Na2 Gd1 35.1(2) 3_545 3_545 ? Gd2 Na2 Gd1 96.65(10) . 3_545 ? C4 O1 Gd1 125.5(6) . . ? C6 O3 Gd1 125.0(6) . . ? C8 O5 Gd1 124.1(7) . . ? C8 O5 Na2 116.3(6) . 3_455 ? Gd1 O5 Na2 117.4(3) . 3_455 ? C10 O7 Gd1 124.2(6) . . ? C10 O7 Na1 124.1(6) . . ? Gd1 O7 Na1 109.6(3) . . ? Gd1 O10 Na1 107.9(3) . . ? Gd1 O11 Na2 108.9(3) . 3_455 ? C14 O12 Gd2 126.3(6) . . ? C16 O14 Gd2 126.1(6) . . ? C18 O16 Gd2 123.9(7) . . ? C18 O16 Na2 125.6(7) . . ? Gd2 O16 Na2 108.9(3) . . ? C20 O18 Gd2 123.6(7) . . ? C20 O18 Na1 119.0(7) . . ? Gd2 O18 Na1 115.0(3) . . ? Gd2 O21 Na2 107.4(3) . . ? Na1 O22 Gd2 106.7(4) . . ? C3 N1 C5 111.0(9) . . ? C3 N1 C1 111.6(9) . . ? C5 N1 C1 108.5(9) . . ? C3 N1 Gd1 108.5(6) . . ? C5 N1 Gd1 107.9(6) . . ? C1 N1 Gd1 109.3(6) . . ? C9 N2 C7 109.2(10) . . ? C9 N2 C2 110.8(9) . . ? C7 N2 C2 110.3(8) . . ? C9 N2 Gd1 108.3(7) . . ? C7 N2 Gd1 108.1(6) . . ? C2 N2 Gd1 110.1(7) . . ? C11 N3 C13 108.8(8) . . ? C11 N3 C15 110.7(9) . . ? C13 N3 C15 109.4(8) . . ? C11 N3 Gd2 109.8(6) . . ? C13 N3 Gd2 108.1(6) . . ? C15 N3 Gd2 110.0(6) . . ? C19 N4 C12 110.2(8) . . ? C19 N4 C17 109.5(9) . . ? C12 N4 C17 108.8(9) . . ? C19 N4 Gd2 107.8(7) . . ? C12 N4 Gd2 113.0(6) . . ? C17 N4 Gd2 107.4(7) . . ? C2 C1 N1 112.7(9) . . ? C1 C2 N2 112.1(9) . . ? N1 C3 C4 115.0(9) . . ? O1 C4 O2 125.1(9) . . ? O1 C4 C3 118.9(8) . . ? O2 C4 C3 116.0(9) . . ? N1 C5 C6 111.0(8) . . ? O4 C6 O3 124.6(9) . . ? O4 C6 C5 118.4(9) . . ? O3 C6 C5 116.9(8) . . ? N2 C7 C8 112.8(8) . . ? O5 C8 O6 125.7(11) . . ? O5 C8 C7 116.8(9) . . ? O6 C8 C7 117.3(10) . . ? N2 C9 C10 114.1(11) . . ? O8 C10 O7 124.5(10) . . ? O8 C10 C9 118.1(11) . . ? O7 C10 C9 117.3(9) . . ? N3 C11 C12 113.3(9) . . ? N4 C12 C11 111.1(9) . . ? N3 C13 C14 110.9(8) . . ? O13 C14 O12 125.0(10) . . ? O13 C14 C13 118.3(9) . . ? O12 C14 C13 116.4(8) . . ? N3 C15 C16 113.7(9) . . ? O15 C16 O14 126.1(9) . . ? O15 C16 C15 116.0(10) . . ? O14 C16 C15 117.9(9) . . ? N4 C17 C18 112.9(10) . . ? O16 C18 O17 125.2(10) . . ? O16 C18 C17 119.0(9) . . ? O17 C18 C17 115.7(11) . . ? N4 C19 C20 113.7(9) . . ? O19 C20 O18 124.8(12) . . ? O19 C20 C19 119.1(11) . . ? O18 C20 C19 116.1(9) . . ? 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 C3 N1 C1 C2 75.4(11) . . . . ? C5 N1 C1 C2 -162.0(9) . . . . ? Gd1 N1 C1 C2 -44.6(10) . . . . ? N1 C1 C2 N2 62.6(12) . . . . ? C9 N2 C2 C1 75.4(13) . . . . ? C7 N2 C2 C1 -163.6(10) . . . . ? Gd1 N2 C2 C1 -44.4(11) . . . . ? C5 N1 C3 C4 142.4(10) . . . . ? C1 N1 C3 C4 -96.5(11) . . . . ? Gd1 N1 C3 C4 24.0(12) . . . . ? Gd1 O1 C4 O2 167.2(9) . . . . ? Gd1 O1 C4 C3 -12.9(14) . . . . ? N1 C3 C4 O1 -10.9(16) . . . . ? N1 C3 C4 O2 169.1(10) . . . . ? C3 N1 C5 C6 -158.9(9) . . . . ? C1 N1 C5 C6 78.1(11) . . . . ? Gd1 N1 C5 C6 -40.2(10) . . . . ? Gd1 O3 C6 O4 -168.1(9) . . . . ? Gd1 O3 C6 C5 12.6(13) . . . . ? N1 C5 C6 O4 -156.9(10) . . . . ? N1 C5 C6 O3 22.4(14) . . . . ? C9 N2 C7 C8 -85.7(11) . . . . ? C2 N2 C7 C8 152.3(10) . . . . ? Gd1 N2 C7 C8 31.9(10) . . . . ? Gd1 O5 C8 O6 -160.8(9) . . . . ? Na2 O5 C8 O6 36.9(14) 3_455 . . . ? Gd1 O5 C8 C7 24.5(12) . . . . ? Na2 O5 C8 C7 -137.8(7) 3_455 . . . ? N2 C7 C8 O5 -39.0(13) . . . . ? N2 C7 C8 O6 145.9(10) . . . . ? C7 N2 C9 C10 82.2(13) . . . . ? C2 N2 C9 C10 -156.1(11) . . . . ? Gd1 N2 C9 C10 -35.3(13) . . . . ? Gd1 O7 C10 O8 -179.1(9) . . . . ? Na1 O7 C10 O8 -16.8(16) . . . . ? Gd1 O7 C10 C9 -3.8(14) . . . . ? Na1 O7 C10 C9 158.5(9) . . . . ? N2 C9 C10 O8 -155.7(11) . . . . ? N2 C9 C10 O7 28.6(17) . . . . ? C13 N3 C11 C12 161.9(9) . . . . ? C15 N3 C11 C12 -77.9(10) . . . . ? Gd2 N3 C11 C12 43.8(10) . . . . ? C19 N4 C12 C11 162.6(9) . . . . ? C17 N4 C12 C11 -77.3(11) . . . . ? Gd2 N4 C12 C11 41.9(9) . . . . ? N3 C11 C12 N4 -59.3(11) . . . . ? C11 N3 C13 C14 -78.4(11) . . . . ? C15 N3 C13 C14 160.6(9) . . . . ? Gd2 N3 C13 C14 40.8(10) . . . . ? Gd2 O12 C14 O13 168.2(9) . . . . ? Gd2 O12 C14 C13 -6.3(15) . . . . ? N3 C13 C14 O13 158.5(10) . . . . ? N3 C13 C14 O12 -26.7(14) . . . . ? C11 N3 C15 C16 97.8(11) . . . . ? C13 N3 C15 C16 -142.3(10) . . . . ? Gd2 N3 C15 C16 -23.7(12) . . . . ? Gd2 O14 C16 O15 -164.8(9) . . . . ? Gd2 O14 C16 C15 12.4(15) . . . . ? N3 C15 C16 O15 -171.7(10) . . . . ? N3 C15 C16 O14 10.8(16) . . . . ? C19 N4 C17 C18 -83.5(12) . . . . ? C12 N4 C17 C18 156.0(9) . . . . ? Gd2 N4 C17 C18 33.3(11) . . . . ? Gd2 O16 C18 O17 178.8(8) . . . . ? Na2 O16 C18 O17 14.7(16) . . . . ? Gd2 O16 C18 C17 1.3(14) . . . . ? Na2 O16 C18 C17 -162.9(7) . . . . ? N4 C17 C18 O16 -26.0(15) . . . . ? N4 C17 C18 O17 156.3(10) . . . . ? C12 N4 C19 C20 -155.3(10) . . . . ? C17 N4 C19 C20 84.9(12) . . . . ? Gd2 N4 C19 C20 -31.6(11) . . . . ? Gd2 O18 C20 O19 158.4(10) . . . . ? Na1 O18 C20 O19 -39.9(15) . . . . ? Gd2 O18 C20 C19 -24.1(13) . . . . ? Na1 O18 C20 C19 137.6(8) . . . . ? N4 C19 C20 O19 -143.9(12) . . . . ? N4 C19 C20 O18 38.4(14) . . . . ? _refine_diff_density_max 0.601 _refine_diff_density_min -0.844 _refine_diff_density_rms 0.076 _shelxl_version_number 2013-4 _shelx_res_file ; TITL mm399 in Cc CELL 0.71073 12.06410 19.32700 18.67580 90.0000 108.7327 90.0000 ZERR 8.00 0.00040 0.00060 0.00060 0.0000 0.0013 0.0000 LATT -7 SYMM X, -Y, 0.5+Z SFAC C H N O NA GD UNIT 80 224 16 128 8 8 TEMP -73.150 SIZE 0.16 0.19 0.24 L.S. 80 ACTA CONF BOND FMAP 2 PLAN 5 LIST 0 TWIN -1 0 0 0 -1 0 1 0 1 OMIT 0 8 -3 OMIT 0 2 0 OMIT 0 8 3 OMIT 0 20 -5 OMIT 4 2 -5 OMIT -6 4 -6 OMIT 4 10 5 OMIT -1 5 -2 OMIT 0 4 0 OMIT -3 13 -4 OMIT 8 14 -11 OMIT 1 5 -3 OMIT 0 14 1 OMIT 6 10 10 OMIT 2 4 -8 OMIT -4 14 3 OMIT -4 4 -11 OMIT -1 15 -1 OMIT -4 4 -8 OMIT 10 2 0 OMIT -8 10 3 OMIT -1 1 -4 OMIT 3 9 -3 OMIT -12 4 0 OMIT -11 11 8 OMIT -6 12 -14 OMIT 2 12 8 OMIT 1 3 -12 OMIT 1 5 -11 OMIT -9 9 6 OMIT -7 7 -4 OMIT 0 6 -9 OMIT 0 10 13 OMIT 0 2 -7 OMIT 13 3 -16 OMIT 10 14 -18 OMIT 2 6 2 OMIT -7 7 9 OMIT 0 8 0 OMIT 0 8 -2 OMIT -6 18 -8 OMIT 4 4 -2 OMIT -2 18 14 OMIT -2 16 -8 OMIT 2 6 -4 OMIT 7 7 -9 OMIT -4 8 -16 OMIT -2 12 7 OMIT 8 10 -20 OMIT -5 19 -8 WGHT 0.037100 7.010800 BASF 0.42114 FVAR 0.06698 GD1 6 0.067288 0.541233 0.720369 11.00000 0.00816 0.00912 = 0.00949 0.00002 0.00203 0.00082 GD2 6 0.382008 0.293416 0.841219 11.00000 0.00747 0.00908 = 0.01003 0.00016 0.00187 0.00093 NA1 5 0.398518 0.483021 0.758814 11.00000 0.02244 0.02072 = 0.02239 0.00438 0.00637 0.00050 NA2 5 0.670318 0.241163 0.791348 11.00000 0.02282 0.02635 = 0.02338 -0.00459 0.00251 -0.00095 O1 4 -0.106784 0.606685 0.702336 11.00000 0.00990 0.01330 = 0.01439 0.00084 0.00339 0.00249 O2 4 -0.295884 0.615464 0.690454 11.00000 0.01316 0.01911 = 0.03922 -0.00639 0.00502 0.00714 O3 4 0.085433 0.419832 0.691756 11.00000 0.01276 0.01108 = 0.01495 -0.00231 0.00164 0.00319 O4 4 0.019896 0.311565 0.679167 11.00000 0.01597 0.01070 = 0.04275 -0.00214 -0.00286 0.00035 O5 4 0.127650 0.653068 0.691535 11.00000 0.02478 0.01398 = 0.01605 -0.00266 0.00918 -0.00272 O6 4 0.166583 0.723806 0.608254 11.00000 0.03358 0.03994 = 0.03333 0.01523 0.00880 -0.01500 O7 4 0.221156 0.526733 0.663751 11.00000 0.00828 0.02206 = 0.01304 -0.00027 0.00325 -0.00006 O8 4 0.282166 0.517581 0.562837 11.00000 0.01699 0.06189 = 0.01721 -0.00809 0.00742 0.00637 O9 4 -0.009951 0.487940 0.811073 11.00000 0.02666 0.01509 = 0.01738 0.00316 0.01317 0.00973 AFIX 3 H9C 2 0.040192 0.453219 0.841020 11.00000 -1.50000 H9D 2 -0.049055 0.514673 0.842544 11.00000 -1.50000 AFIX 0 O10 4 0.239209 0.493534 0.816043 11.00000 0.01319 0.01403 = 0.01123 -0.00132 0.00274 0.00154 AFIX 3 H10A 2 0.233107 0.445219 0.825141 11.00000 -1.50000 H10B 2 0.277163 0.518559 0.864949 11.00000 -1.50000 AFIX 0 O11 4 0.114062 0.622364 0.831739 11.00000 0.01598 0.01776 = 0.01228 0.00094 0.00459 0.00514 AFIX 3 H11C 2 0.048316 0.641942 0.842459 11.00000 -1.50000 H11D 2 0.169181 0.600774 0.878550 11.00000 -1.50000 AFIX 0 O12 4 0.429150 0.173001 0.869727 11.00000 0.01535 0.01556 = 0.03286 0.00487 0.01456 0.00066 O13 4 0.381849 0.065075 0.889731 11.00000 0.02490 0.01249 = 0.04304 0.00378 0.02213 0.00701 O14 4 0.226053 0.358355 0.859044 11.00000 0.01540 0.01136 = 0.02726 0.00369 0.01224 0.00184 O15 4 0.048264 0.363976 0.872725 11.00000 0.02033 0.01861 = 0.03606 0.00944 0.01577 0.00868 O16 4 0.591850 0.280593 0.893760 11.00000 0.01557 0.02137 = 0.01220 -0.00170 0.00078 0.00412 O17 4 0.753843 0.272250 0.990730 11.00000 0.01125 0.04187 = 0.01708 0.00602 0.00124 0.00219 O18 4 0.464527 0.405172 0.863233 11.00000 0.01364 0.01792 = 0.01874 -0.00196 0.00294 -0.00388 O19 4 0.586026 0.477131 0.942867 11.00000 0.04456 0.04493 = 0.02948 -0.01156 0.01137 -0.02829 O20 4 0.211484 0.239015 0.754139 11.00000 0.01464 0.01420 = 0.02513 -0.00307 0.00258 -0.00234 AFIX 3 H20A 2 0.221633 0.200905 0.724132 11.00000 -1.50000 H20B 2 0.144759 0.268961 0.724200 11.00000 -1.50000 AFIX 0 O21 4 0.451881 0.242494 0.741842 11.00000 0.01942 0.01215 = 0.01653 -0.00291 0.00732 0.00186 AFIX 3 H21A 2 0.425918 0.196046 0.728949 11.00000 -1.50000 H21B 2 0.441160 0.270642 0.694794 11.00000 -1.50000 AFIX 0 O22 4 0.306378 0.369822 0.724639 11.00000 0.01458 0.01605 = 0.01509 0.00182 0.00394 0.00472 AFIX 3 H22A 2 0.226482 0.384145 0.709457 11.00000 -1.50000 H22B 2 0.327280 0.352257 0.679850 11.00000 -1.50000 AFIX 0 O23 4 0.491326 0.487830 0.664429 11.00000 0.03908 0.13346 = 0.05961 0.02087 0.02279 0.02885 AFIX 3 H23A 2 0.518242 0.534373 0.664643 11.00000 -1.50000 H23B 2 0.537212 0.455910 0.641971 11.00000 -1.50000 AFIX 0 O24 4 0.481608 0.591812 0.789245 11.00000 0.05861 0.04062 = 0.09721 -0.01055 -0.01357 -0.01776 AFIX 3 H24A 2 0.545109 0.587230 0.835251 11.00000 -1.50000 H24B 2 0.479819 0.639820 0.768189 11.00000 -1.50000 AFIX 0 O25 4 0.654759 0.356196 0.748580 11.00000 0.09339 0.03418 = 0.03205 0.00358 0.02316 -0.00614 AFIX 3 H25A 2 0.622238 0.369354 0.696682 11.00000 -1.50000 H25B 2 0.658885 0.397264 0.782401 11.00000 -1.50000 AFIX 0 O26 4 0.858894 0.260509 0.884782 11.00000 0.02072 0.04536 = 0.03105 -0.00440 0.01198 -0.00289 AFIX 3 H26A 2 0.825765 0.276988 0.921830 11.00000 -1.50000 H26B 2 0.941780 0.276951 0.896883 11.00000 -1.50000 AFIX 0 O27 4 0.576365 0.356250 0.581747 11.00000 0.04207 0.05552 = 0.05348 0.00306 0.01594 -0.00036 AFIX 3 H27A 2 0.577554 0.349836 0.525952 11.00000 -1.50000 H27B 2 0.613173 0.312577 0.607899 11.00000 -1.50000 AFIX 0 O28 4 -0.112258 0.213767 0.725067 11.00000 0.07077 0.05289 = 0.03823 0.00756 0.00709 -0.03043 AFIX 3 H28A 2 -0.184877 0.224321 0.687319 11.00000 -1.50000 H28B 2 -0.060312 0.255685 0.736340 11.00000 -1.50000 AFIX 0 O29 4 0.871506 0.187854 1.109385 11.00000 0.02847 0.03757 = 0.01220 0.00230 0.00173 -0.00092 AFIX 3 H29A 2 0.823981 0.213794 1.067143 11.00000 -1.50000 H29B 2 0.935226 0.163131 1.095688 11.00000 -1.50000 AFIX 0 O30 4 0.177050 -0.014169 0.827400 11.00000 0.05845 0.06688 = 0.03323 -0.01088 0.01894 -0.02603 AFIX 3 H30A 2 0.246859 0.012667 0.837552 11.00000 -1.50000 H30B 2 0.153210 -0.018199 0.874209 11.00000 -1.50000 AFIX 0 O31 4 0.283425 0.561490 0.945941 11.00000 0.01964 0.02452 = 0.02202 0.00086 0.00091 -0.00450 AFIX 3 H31A 2 0.279352 0.535180 0.988453 11.00000 -1.50000 H31B 2 0.361925 0.584356 0.957602 11.00000 -1.50000 AFIX 0 O32 4 0.467371 0.633834 0.931179 11.00000 0.03896 0.03483 = 0.06148 0.00548 0.01592 -0.00547 AFIX 3 H32A 2 0.426598 0.676682 0.917366 11.00000 -1.50000 H32B 2 0.503843 0.619625 0.891907 11.00000 -1.50000 AFIX 0 N1 3 -0.129867 0.474359 0.646212 11.00000 0.00959 0.01915 = 0.01093 -0.00177 0.00113 0.00051 N2 3 0.000649 0.567135 0.573373 11.00000 0.01676 0.01098 = 0.01542 0.00025 0.00155 0.00039 N3 3 0.265091 0.227576 0.920904 11.00000 0.01340 0.00417 = 0.02460 0.00100 0.00891 0.00519 N4 3 0.461697 0.323126 0.985419 11.00000 0.00794 0.02292 = 0.01246 0.00128 0.00297 0.00575 C1 1 -0.146312 0.475459 0.564063 11.00000 0.01306 0.01274 = 0.02065 -0.00255 0.00030 -0.00190 AFIX 23 H1A 2 -0.093062 0.441165 0.552992 11.00000 -1.20000 H1B 2 -0.227634 0.461542 0.535897 11.00000 -1.20000 AFIX 0 C2 1 -0.123111 0.544791 0.537048 11.00000 0.00954 0.02922 = 0.01290 0.00201 -0.00491 -0.00255 AFIX 23 H2A 2 -0.176052 0.579214 0.548248 11.00000 -1.20000 H2B 2 -0.140453 0.543287 0.481536 11.00000 -1.20000 AFIX 0 C3 1 -0.227402 0.507972 0.663203 11.00000 0.00672 0.01889 = 0.02567 -0.00670 0.00504 0.00121 AFIX 23 H3A 2 -0.244509 0.481583 0.703867 11.00000 -1.20000 H3B 2 -0.297639 0.505416 0.617699 11.00000 -1.20000 AFIX 0 C4 1 -0.207022 0.582325 0.687293 11.00000 0.00698 0.01411 = 0.01472 -0.00147 -0.00061 0.00736 C5 1 -0.116937 0.401605 0.672153 11.00000 0.01062 0.00795 = 0.03631 0.00220 0.01173 0.00131 AFIX 23 H5A 2 -0.175000 0.372506 0.634779 11.00000 -1.20000 H5B 2 -0.132671 0.398221 0.720900 11.00000 -1.20000 AFIX 0 C6 1 0.005229 0.374997 0.681949 11.00000 0.00922 0.01284 = 0.01566 -0.00115 -0.00065 0.00194 C7 1 0.012080 0.642181 0.563052 11.00000 0.01719 0.02313 = 0.01231 0.00587 -0.00274 0.00014 AFIX 23 H7A 2 -0.062081 0.665249 0.561152 11.00000 -1.20000 H7B 2 0.025136 0.650308 0.514035 11.00000 -1.20000 AFIX 0 C8 1 0.112221 0.674580 0.626001 11.00000 0.01579 0.01422 = 0.02575 0.00619 0.00985 0.00339 C9 1 0.079425 0.529811 0.540934 11.00000 0.01562 0.04439 = 0.01507 -0.00464 0.00637 0.00306 AFIX 23 H9A 2 0.078022 0.552972 0.493369 11.00000 -1.20000 H9B 2 0.049317 0.482209 0.528050 11.00000 -1.20000 AFIX 0 C10 1 0.203841 0.525817 0.592186 11.00000 0.01474 0.01805 = 0.01440 -0.00271 0.00751 0.00121 C11 1 0.331577 0.231149 1.001921 11.00000 0.01995 0.02405 = 0.01261 0.00727 0.00852 0.00556 AFIX 23 H11A 2 0.396193 0.197068 1.013446 11.00000 -1.20000 H11B 2 0.279487 0.218020 1.031239 11.00000 -1.20000 AFIX 0 C12 1 0.381720 0.301365 1.026954 11.00000 0.01105 0.01550 = 0.01517 -0.00033 0.00202 0.00364 AFIX 23 H12A 2 0.317322 0.335362 1.018091 11.00000 -1.20000 H12B 2 0.424967 0.300439 1.081851 11.00000 -1.20000 AFIX 0 C13 1 0.252942 0.154693 0.897441 11.00000 0.01453 0.01155 = 0.01464 0.00308 0.00659 0.00141 AFIX 23 H13A 2 0.187590 0.149959 0.849420 11.00000 -1.20000 H13B 2 0.234126 0.126530 0.936293 11.00000 -1.20000 AFIX 0 C14 1 0.364489 0.128147 0.886797 11.00000 0.01767 0.01565 = 0.01540 0.00285 0.00554 0.00394 C15 1 0.147390 0.258577 0.905491 11.00000 0.01961 0.01230 = 0.02774 0.00616 0.01339 0.00394 AFIX 23 H15A 2 0.125855 0.256948 0.952342 11.00000 -1.20000 H15B 2 0.089799 0.230255 0.866902 11.00000 -1.20000 AFIX 0 C16 1 0.139139 0.333756 0.877640 11.00000 0.02135 0.01335 = 0.01302 0.00010 0.00418 -0.00332 C17 1 0.576976 0.285885 1.018163 11.00000 0.01529 0.02936 = 0.01335 0.00548 0.00323 0.00951 AFIX 23 H17A 2 0.562005 0.238895 1.034069 11.00000 -1.20000 H17B 2 0.625275 0.310991 1.063707 11.00000 -1.20000 AFIX 0 C18 1 0.645727 0.279856 0.962036 11.00000 0.01760 0.01985 = 0.01293 0.00533 0.00733 0.00034 C19 1 0.481209 0.398408 0.992595 11.00000 0.02791 0.01911 = 0.02264 -0.00839 0.00510 -0.00718 AFIX 23 H19A 2 0.543429 0.408126 1.041001 11.00000 -1.20000 H19B 2 0.408593 0.421058 0.994475 11.00000 -1.20000 AFIX 0 C20 1 0.515764 0.429692 0.929134 11.00000 0.01518 0.01888 = 0.02136 -0.00291 0.00044 -0.00223 HKLF 4 REM mm399 in Cc REM R1 = 0.0216 for 9577 Fo > 4sig(Fo) and 0.0217 for all 9608 data REM 542 parameters refined using 2 restraints END WGHT 0.0338 10.3488 REM Highest difference peak 0.601, deepest hole -0.844, 1-sigma level 0.076 Q1 1 0.0577 0.5400 0.7423 11.00000 0.05 0.60 Q2 1 0.3656 0.2908 0.8699 11.00000 0.05 0.53 Q3 1 0.2941 0.2823 0.8058 11.00000 0.05 0.43 Q4 1 0.3789 0.3325 0.8431 11.00000 0.05 0.43 Q5 1 0.0817 0.5417 0.6790 11.00000 0.05 0.40 ; _shelx_res_checksum 19463 _exptl_crystal_preparation 'Magnetic properties'