# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_2 _database_code_depnum_ccdc_archive 'CCDC 886479' #TrackingRef 'D-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 Co N12 O4 S' _chemical_formula_weight 557.43 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M I4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' _cell_length_a 12.7419(4) _cell_length_b 12.7419(4) _cell_length_c 14.2617(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2315.47(18) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1140 _exptl_absorpt_coefficient_mu 0.885 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7184 _exptl_absorpt_correction_T_max 0.8090 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4464 _diffrn_reflns_av_R_equivalents 0.0155 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.98 _reflns_number_total 2133 _reflns_number_gt 2018 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+0.0369P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.002(11) _refine_ls_number_reflns 2133 _refine_ls_number_parameters 172 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0245 _refine_ls_R_factor_gt 0.0229 _refine_ls_wR_factor_ref 0.0583 _refine_ls_wR_factor_gt 0.0575 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 1.0000 1.0000 0.95147(2) 0.02560(11) Uani 1 2 d S . . N3 N 1.09055(13) 0.91438(13) 1.05314(10) 0.0253(3) Uani 1 1 d . . . N4 N 1.22835(13) 0.91359(12) 1.14706(11) 0.0259(4) Uani 1 1 d . . . H4A H 1.2872 0.9330 1.1742 0.031 Uiso 1 1 calc R . . N2 N 0.70667(14) 0.88212(13) 1.03222(11) 0.0276(4) Uani 1 1 d . . . H2A H 0.6508 0.8943 1.0668 0.033 Uiso 1 1 calc R . . N6 N 1.03444(13) 0.88042(13) 0.68087(10) 0.0300(4) Uani 1 1 d . . . H6A H 1.0243 0.8940 0.6210 0.036 Uiso 1 1 calc R . . N1 N 0.86330(13) 0.90167(13) 0.96813(11) 0.0287(4) Uani 1 1 d . . . C2 C 1.16941(16) 0.82612(16) 1.16791(13) 0.0294(4) Uani 1 1 d . . . H2B H 1.1849 0.7746 1.2140 0.035 Uiso 1 1 calc R . . C4 C 0.81702(18) 0.81207(16) 0.93264(14) 0.0354(5) Uani 1 1 d . . . H4B H 0.8477 0.7663 0.8878 0.042 Uiso 1 1 calc R . . C8 C 1.02001(15) 0.94679(16) 0.75258(13) 0.0271(4) Uani 1 1 d . . . C3 C 1.17827(14) 0.96355(15) 1.07700(12) 0.0234(4) Uani 1 1 d . . . C1 C 1.08508(16) 0.82768(17) 1.11000(14) 0.0293(4) Uani 1 1 d . . . H1A H 1.0307 0.7767 1.1089 0.035 Uiso 1 1 calc R . . C6 C 0.79429(16) 0.94077(15) 1.02850(13) 0.0256(4) Uani 1 1 d . . . C7 C 1.07334(17) 0.80223(17) 0.81257(15) 0.0326(5) Uani 1 1 d . . . N5 N 1.04370(14) 0.90311(13) 0.83425(12) 0.0298(4) Uani 1 1 d . . . C9 C 1.06796(18) 0.78753(17) 0.71848(15) 0.0336(5) Uani 1 1 d . . . C5 C 0.72101(18) 0.79982(16) 0.97192(14) 0.0337(5) Uani 1 1 d . . . H5A H 0.6728 0.7446 0.9599 0.040 Uiso 1 1 calc R . . S1 S 0.5000 0.0000 0.17889(4) 0.03082(19) Uani 1 2 d S . . O1 O 0.40821(11) -0.02343(12) 0.23885(9) 0.0341(3) Uani 1 1 d . . . O2 O 0.47841(14) 0.09096(14) 0.11995(12) 0.0543(5) Uani 1 1 d . . . H7A H 1.0927(16) 0.7532(17) 0.8634(16) 0.030(6) Uiso 1 1 d . . . H9A H 1.0766(18) 0.735(2) 0.6811(17) 0.041(7) Uiso 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 Co1 0.0267(2) 0.0291(2) 0.02105(18) 0.000 0.000 0.00658(16) N3 0.0269(9) 0.0264(9) 0.0225(7) 0.0012(6) 0.0015(6) 0.0026(7) N4 0.0248(9) 0.0271(9) 0.0258(8) 0.0023(7) 0.0001(7) -0.0013(7) N2 0.0306(9) 0.0295(9) 0.0227(7) -0.0009(6) -0.0042(6) -0.0029(7) N6 0.0333(9) 0.0330(9) 0.0238(8) -0.0025(7) 0.0030(7) 0.0060(7) N1 0.0317(9) 0.0296(9) 0.0249(8) -0.0043(7) -0.0038(7) 0.0052(7) C2 0.0295(11) 0.0275(10) 0.0312(10) 0.0076(8) 0.0000(8) -0.0022(9) C4 0.0457(13) 0.0307(11) 0.0298(10) -0.0089(9) -0.0072(9) 0.0045(9) C8 0.0290(11) 0.0282(11) 0.0240(9) -0.0002(8) 0.0022(7) 0.0052(9) C3 0.0250(10) 0.0262(10) 0.0189(7) -0.0020(7) 0.0022(7) 0.0035(8) C1 0.0284(11) 0.0279(11) 0.0315(9) 0.0041(8) 0.0007(8) -0.0028(9) C6 0.0302(11) 0.0253(10) 0.0213(8) 0.0012(7) -0.0057(7) 0.0025(8) C7 0.0335(12) 0.0277(11) 0.0366(11) 0.0030(9) -0.0003(9) 0.0096(9) N5 0.0324(9) 0.0308(9) 0.0262(8) 0.0017(7) 0.0001(7) 0.0093(7) C9 0.0348(12) 0.0290(11) 0.0371(11) -0.0059(9) 0.0024(8) 0.0054(9) C5 0.0441(13) 0.0284(11) 0.0285(9) -0.0063(8) -0.0115(9) -0.0021(9) S1 0.0327(4) 0.0374(4) 0.0224(4) 0.000 0.000 -0.0127(3) O1 0.0272(8) 0.0484(9) 0.0267(7) -0.0050(6) -0.0001(6) -0.0098(7) O2 0.0563(11) 0.0553(11) 0.0513(10) 0.0225(9) -0.0236(8) -0.0286(9) _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 Co1 N3 2.1503(16) . ? Co1 N3 2.1503(16) 6_664 ? Co1 N5 2.1515(17) 6_664 ? Co1 N5 2.1515(17) . ? Co1 N1 2.1588(17) 6_664 ? Co1 N1 2.1588(17) . ? N3 C3 1.326(3) . ? N3 C1 1.372(2) . ? N4 C3 1.346(2) . ? N4 C2 1.377(2) . ? N4 H4A 0.8800 . ? N2 C6 1.345(3) . ? N2 C5 1.368(3) . ? N2 H2A 0.8800 . ? N6 C8 1.340(2) . ? N6 C9 1.368(3) . ? N6 H6A 0.8800 . ? N1 C6 1.328(3) . ? N1 C4 1.381(3) . ? C2 C1 1.355(3) . ? C2 H2B 0.9500 . ? C4 C5 1.355(3) . ? C4 H4B 0.9500 . ? C8 N5 1.326(3) . ? C8 C8 1.449(4) 6_664 ? C3 C6 1.445(3) 6_664 ? C1 H1A 0.9500 . ? C6 C3 1.445(3) 6_664 ? C7 C9 1.357(3) . ? C7 N5 1.375(3) . ? C7 H7A 0.99(2) . ? C9 H9A 0.87(3) . ? C5 H5A 0.9500 . ? S1 O2 1.4579(16) 6_544 ? S1 O2 1.4579(16) . ? S1 O1 1.4794(14) 6_544 ? S1 O1 1.4794(14) . ? 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 N3 Co1 N3 95.20(8) . 6_664 ? N3 Co1 N5 162.54(6) . 6_664 ? N3 Co1 N5 95.39(6) 6_664 6_664 ? N3 Co1 N5 95.39(6) . . ? N3 Co1 N5 162.54(6) 6_664 . ? N5 Co1 N5 78.03(9) 6_664 . ? N3 Co1 N1 77.72(6) . 6_664 ? N3 Co1 N1 93.68(6) 6_664 6_664 ? N5 Co1 N1 87.78(6) 6_664 6_664 ? N5 Co1 N1 102.11(7) . 6_664 ? N3 Co1 N1 93.68(6) . . ? N3 Co1 N1 77.72(6) 6_664 . ? N5 Co1 N1 102.11(7) 6_664 . ? N5 Co1 N1 87.78(6) . . ? N1 Co1 N1 167.36(8) 6_664 . ? C3 N3 C1 105.75(16) . . ? C3 N3 Co1 112.69(12) . . ? C1 N3 Co1 141.24(14) . . ? C3 N4 C2 106.54(17) . . ? C3 N4 H4A 126.7 . . ? C2 N4 H4A 126.7 . . ? C6 N2 C5 106.87(18) . . ? C6 N2 H2A 126.6 . . ? C5 N2 H2A 126.6 . . ? C8 N6 C9 106.84(17) . . ? C8 N6 H6A 126.6 . . ? C9 N6 H6A 126.6 . . ? C6 N1 C4 105.38(17) . . ? C6 N1 Co1 112.83(13) . . ? C4 N1 Co1 141.62(14) . . ? C1 C2 N4 106.80(18) . . ? C1 C2 H2B 126.6 . . ? N4 C2 H2B 126.6 . . ? C5 C4 N1 109.22(18) . . ? C5 C4 H4B 125.4 . . ? N1 C4 H4B 125.4 . . ? N5 C8 N6 111.99(17) . . ? N5 C8 C8 118.24(11) . 6_664 ? N6 C8 C8 129.73(11) . 6_664 ? N3 C3 N4 111.52(17) . . ? N3 C3 C6 118.68(17) . 6_664 ? N4 C3 C6 129.79(18) . 6_664 ? C2 C1 N3 109.37(19) . . ? C2 C1 H1A 125.3 . . ? N3 C1 H1A 125.3 . . ? N1 C6 N2 111.53(17) . . ? N1 C6 C3 117.84(18) . 6_664 ? N2 C6 C3 130.62(18) . 6_664 ? C9 C7 N5 109.74(19) . . ? C9 C7 H7A 130.6(12) . . ? N5 C7 H7A 119.6(12) . . ? C8 N5 C7 104.92(18) . . ? C8 N5 Co1 112.50(12) . . ? C7 N5 Co1 141.47(14) . . ? C7 C9 N6 106.51(18) . . ? C7 C9 H9A 135.3(16) . . ? N6 C9 H9A 118.0(16) . . ? C4 C5 N2 106.99(19) . . ? C4 C5 H5A 126.5 . . ? N2 C5 H5A 126.5 . . ? O2 S1 O2 109.59(16) 6_544 . ? O2 S1 O1 110.15(10) 6_544 6_544 ? O2 S1 O1 108.79(8) . 6_544 ? O2 S1 O1 108.79(8) 6_544 . ? O2 S1 O1 110.15(10) . . ? O1 S1 O1 109.37(11) 6_544 . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.151 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.041 data_ybh-tyh512-2 _database_code_depnum_ccdc_archive 'CCDC 886480' #TrackingRef 'D-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N12 Ni O4 S' _chemical_formula_weight 557.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M I4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' _cell_length_a 12.6811(4) _cell_length_b 12.6811(4) _cell_length_c 14.2077(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2284.74(16) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 2.565 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6279 _exptl_absorpt_correction_T_max 0.6279 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3510 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.67 _diffrn_reflns_theta_max 62.51 _reflns_number_total 1636 _reflns_number_gt 1533 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0390P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment contr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(3) _refine_ls_number_reflns 1636 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0741 _refine_ls_wR_factor_gt 0.0703 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.0000 0.0000 0.01688(4) 0.0230(2) Uani 1 2 d S . . C1 C 0.0528(2) -0.0222(2) 0.2137(2) 0.0236(6) Uani 1 1 d . . . C2 C 0.2126(2) -0.0722(3) 0.2470(2) 0.0307(7) Uani 1 1 d . . . H2 H 0.2742 -0.0892 0.2791 0.037 Uiso 1 1 calc R . . C3 C 0.1961(2) -0.0784(3) 0.1525(2) 0.0295(7) Uani 1 1 d . . . H3 H 0.2460 -0.1001 0.1085 0.035 Uiso 1 1 calc R . . C4 C -0.1695(3) 0.0798(3) -0.1437(2) 0.0283(7) Uani 1 1 d . . . H4 H -0.2186 0.0253 -0.1435 0.034 Uiso 1 1 calc R . . N4 N -0.0850(2) 0.2248(2) -0.17943(18) 0.0252(6) Uani 1 1 d . . . H4A H -0.0666 0.2831 -0.2056 0.030 Uiso 1 1 calc R . . C6 C -0.0347(2) 0.1754(2) -0.1090(2) 0.0220(6) Uani 1 1 d . . . C7 C 0.0597(2) 0.2036(2) -0.0583(2) 0.0222(6) Uani 1 1 d . . . C8 C 0.1863(2) 0.1807(3) 0.0401(2) 0.0303(7) Uani 1 1 d . . . H8 H 0.2302 0.1505 0.0850 0.036 Uiso 1 1 calc R . . C9 C 0.2003(2) 0.2770(3) 0.0000(2) 0.0307(7) Uani 1 1 d . . . H9 H 0.2548 0.3240 0.0125 0.037 Uiso 1 1 calc R . . N1 N 0.0950(2) -0.0479(2) 0.13188(19) 0.0259(5) Uani 1 1 d . . . N2 N 0.1205(2) -0.0360(2) 0.28530(19) 0.0279(6) Uani 1 1 d . . . H2A H 0.1083 -0.0243 0.3439 0.033 Uiso 1 1 calc R . . N3 N -0.0843(2) 0.0865(2) -0.08532(18) 0.0247(6) Uani 1 1 d . . . C5 C -0.1718(3) 0.1643(3) -0.2020(2) 0.0299(7) Uani 1 1 d . . . H5 H -0.2219 0.1787 -0.2480 0.036 Uiso 1 1 calc R . . N5 N 0.0969(2) 0.1349(2) 0.00356(18) 0.0265(6) Uani 1 1 d . . . N6 N 0.1190(2) 0.2918(2) -0.06219(19) 0.0252(6) Uani 1 1 d . . . H6 H 0.1081 0.3464 -0.0968 0.030 Uiso 1 1 calc R . . O1 O -0.02383(18) 0.40756(16) 0.72852(15) 0.0324(5) Uani 1 1 d . . . O2 O 0.0915(2) 0.4771(2) 0.84778(19) 0.0452(7) Uani 1 1 d . . . S1 S 0.0000 0.5000 0.78913(7) 0.0266(3) Uani 1 2 d S . . 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 0.0258(4) 0.0227(4) 0.0204(4) 0.000 0.000 0.0028(3) C1 0.0239(16) 0.0233(15) 0.0237(17) 0.0007(12) 0.0011(13) 0.0006(13) C2 0.0259(16) 0.0301(17) 0.0362(18) 0.0012(14) -0.0031(14) 0.0000(13) C3 0.0210(15) 0.0307(17) 0.0367(19) 0.0025(14) 0.0040(14) 0.0047(13) C4 0.0286(17) 0.0314(17) 0.0247(16) -0.0003(13) -0.0058(13) -0.0031(15) N4 0.0288(13) 0.0244(13) 0.0224(13) 0.0033(11) -0.0035(11) -0.0001(11) C6 0.0260(15) 0.0227(14) 0.0173(14) -0.0031(12) 0.0003(12) 0.0036(12) C7 0.0239(15) 0.0262(16) 0.0164(15) -0.0051(12) 0.0017(12) 0.0024(13) C8 0.0280(16) 0.0366(18) 0.0262(17) -0.0043(14) -0.0072(14) 0.0005(13) C9 0.0290(17) 0.0344(18) 0.0286(17) -0.0101(14) -0.0016(13) -0.0042(14) N1 0.0261(13) 0.0251(13) 0.0266(13) 0.0018(11) -0.0002(11) 0.0051(11) N2 0.0269(13) 0.0325(13) 0.0242(14) 0.0016(12) -0.0017(11) 0.0029(11) N3 0.0272(13) 0.0237(13) 0.0232(13) -0.0007(10) -0.0002(11) 0.0029(11) C5 0.0310(17) 0.0309(17) 0.0278(19) -0.0027(13) -0.0104(13) -0.0025(14) N5 0.0288(14) 0.0282(13) 0.0225(14) -0.0029(11) -0.0018(10) 0.0028(12) N6 0.0302(13) 0.0248(13) 0.0206(13) -0.0048(11) -0.0030(11) -0.0038(11) O1 0.0462(14) 0.0231(12) 0.0280(12) -0.0026(9) 0.0036(10) -0.0046(11) O2 0.0460(15) 0.0438(15) 0.0457(15) 0.0166(12) -0.0168(12) -0.0158(13) S1 0.0306(5) 0.0267(5) 0.0224(7) 0.000 0.000 -0.0057(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 Ni1 N3 2.111(3) 6_444 ? Ni1 N3 2.111(3) . ? Ni1 N5 2.115(3) 6_444 ? Ni1 N5 2.115(3) . ? Ni1 N1 2.119(3) . ? Ni1 N1 2.119(3) 6_444 ? C1 N1 1.320(4) . ? C1 N2 1.343(4) . ? C1 C1 1.453(6) 6_444 ? C2 C3 1.361(5) . ? C2 N2 1.368(4) . ? C3 N1 1.371(4) . ? C4 C5 1.355(5) . ? C4 N3 1.364(4) . ? N4 C6 1.341(4) . ? N4 C5 1.379(4) . ? C6 N3 1.334(4) . ? C6 C7 1.443(4) . ? C7 N5 1.324(4) . ? C7 N6 1.349(4) . ? C8 C9 1.359(5) . ? C8 N5 1.375(4) . ? C9 N6 1.370(4) . ? O1 S1 1.486(2) . ? O2 S1 1.457(2) . ? S1 O2 1.457(2) 6_454 ? S1 O1 1.486(2) 6_454 ? 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 N3 Ni1 N3 93.06(14) 6_444 . ? N3 Ni1 N5 79.18(10) 6_444 6_444 ? N3 Ni1 N5 93.70(10) . 6_444 ? N3 Ni1 N5 93.70(10) 6_444 . ? N3 Ni1 N5 79.18(10) . . ? N5 Ni1 N5 169.74(14) 6_444 . ? N3 Ni1 N1 95.36(10) 6_444 . ? N3 Ni1 N1 165.36(10) . . ? N5 Ni1 N1 99.63(10) 6_444 . ? N5 Ni1 N1 88.32(10) . . ? N3 Ni1 N1 165.36(10) 6_444 6_444 ? N3 Ni1 N1 95.36(10) . 6_444 ? N5 Ni1 N1 88.32(10) 6_444 6_444 ? N5 Ni1 N1 99.63(10) . 6_444 ? N1 Ni1 N1 79.10(14) . 6_444 ? N1 C1 N2 112.1(3) . . ? N1 C1 C1 117.98(18) . 6_444 ? N2 C1 C1 129.75(18) . 6_444 ? C3 C2 N2 106.3(3) . . ? C2 C3 N1 109.7(3) . . ? C5 C4 N3 109.8(3) . . ? C6 N4 C5 107.0(3) . . ? N3 C6 N4 111.1(3) . . ? N3 C6 C7 118.3(3) . . ? N4 C6 C7 130.6(3) . . ? N5 C7 N6 112.0(3) . . ? N5 C7 C6 117.7(3) . . ? N6 C7 C6 130.4(3) . . ? C9 C8 N5 109.2(3) . . ? C8 C9 N6 107.2(3) . . ? C1 N1 C3 105.1(3) . . ? C1 N1 Ni1 112.2(2) . . ? C3 N1 Ni1 141.0(2) . . ? C1 N2 C2 106.7(3) . . ? C6 N3 C4 105.8(3) . . ? C6 N3 Ni1 112.0(2) . . ? C4 N3 Ni1 141.8(2) . . ? C4 C5 N4 106.3(3) . . ? C7 N5 C8 105.4(3) . . ? C7 N5 Ni1 112.6(2) . . ? C8 N5 Ni1 141.9(2) . . ? C7 N6 C9 106.2(3) . . ? O2 S1 O2 110.3(2) . 6_454 ? O2 S1 O1 109.63(14) . . ? O2 S1 O1 109.08(13) 6_454 . ? O2 S1 O1 109.08(13) . 6_454 ? O2 S1 O1 109.63(14) 6_454 6_454 ? O1 S1 O1 109.15(18) . 6_454 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 62.51 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.191 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.045 data_D-4 _database_code_depnum_ccdc_archive 'CCDC 886481' #TrackingRef 'D-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 Mn N12 O4 S' _chemical_formula_weight 553.44 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' Mn Mn 0.3368 0.7283 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M I41 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x+1/2, z+1/4' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-y+1/2, x+1, z+3/4' '-x+1, -y+1, z+1' 'y+1, -x+1/2, z+5/4' _cell_length_a 12.8487(16) _cell_length_b 12.8487(16) _cell_length_c 14.526(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2398.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1132 _exptl_absorpt_coefficient_mu 0.690 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7466 _exptl_absorpt_correction_T_max 0.8744 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4667 _diffrn_reflns_av_R_equivalents 0.1536 _diffrn_reflns_av_sigmaI/netI 0.1343 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2162 _reflns_number_gt 1884 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1021P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.11(3) _refine_ls_number_reflns 2162 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1625 _refine_ls_wR_factor_gt 0.1581 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.002 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.1734(4) 0.0942(4) 0.1068(3) 0.0479(10) Uani 1 1 d . . . H1 H -0.2250 0.0412 0.1077 0.057 Uiso 1 1 calc R . . C2 C -0.1732(4) 0.1773(4) 0.0498(3) 0.0487(10) Uani 1 1 d . . . H2A H -0.2238 0.1934 0.0044 0.058 Uiso 1 1 calc R . . C3 C -0.0371(3) 0.1843(3) 0.1394(3) 0.0390(8) Uani 1 1 d . . . C4 C 0.0588(3) 0.2108(4) 0.1856(3) 0.0427(9) Uani 1 1 d . . . C5 C 0.1902(4) 0.1896(4) 0.2767(4) 0.0590(13) Uani 1 1 d . . . H5 H 0.2374 0.1600 0.3197 0.071 Uiso 1 1 calc R . . C6 C 0.1995(4) 0.2844(5) 0.2375(3) 0.0570(12) Uani 1 1 d . . . H6A H 0.2539 0.3330 0.2481 0.068 Uiso 1 1 calc R . . C7 C 0.0537(4) -0.0179(3) 0.4682(3) 0.0431(9) Uani 1 1 d . . . C8 C 0.2113(4) -0.0630(4) 0.5057(4) 0.0566(12) Uani 1 1 d . . . H8 H 0.2722 -0.0789 0.5401 0.068 Uiso 1 1 calc R . . C9 C 0.1995(4) -0.0668(4) 0.4124(4) 0.0568(12) Uani 1 1 d . . . H9 H 0.2526 -0.0858 0.3702 0.068 Uiso 1 1 calc R . . Mn1 Mn 0.0000 0.0000 0.26549(6) 0.0456(3) Uani 1 2 d S . . N1 N -0.0880(3) 0.0980(3) 0.1632(3) 0.0450(8) Uani 1 1 d . . . N2 N -0.0857(3) 0.2338(3) 0.0703(3) 0.0430(8) Uani 1 1 d . . . H3A H -0.0653 0.2916 0.0433 0.052 Uiso 1 1 calc R . . N3 N 0.1005(3) 0.1425(3) 0.2438(3) 0.0514(9) Uani 1 1 d . . . N4 N 0.1167(3) 0.2978(3) 0.1801(2) 0.0461(8) Uani 1 1 d . . . H4 H 0.1037 0.3528 0.1459 0.055 Uiso 1 1 calc R . . N5 N 0.1004(3) -0.0393(3) 0.3884(3) 0.0534(9) Uani 1 1 d . . . N6 N 0.1170(3) -0.0315(3) 0.5391(3) 0.0480(9) Uani 1 1 d . . . H6 H 0.1011 -0.0220 0.5974 0.058 Uiso 1 1 calc R . . O1 O 0.0882(4) 0.4798(4) 0.0945(3) 0.0958(18) Uani 1 1 d . . . O2 O -0.0233(3) 0.4097(3) -0.0224(2) 0.0568(9) Uani 1 1 d . . . S3 S 0.0000 0.5000 0.03578(11) 0.0503(5) Uani 1 2 d S . . 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 C1 0.051(2) 0.045(2) 0.048(2) 0.0017(19) -0.0068(19) -0.002(2) C2 0.049(2) 0.047(2) 0.051(3) 0.0015(19) -0.0142(19) -0.0067(19) C3 0.043(2) 0.040(2) 0.034(2) -0.0060(16) 0.0023(16) 0.0020(16) C4 0.045(2) 0.050(2) 0.033(2) -0.0083(17) 0.0022(17) 0.0057(18) C5 0.057(3) 0.071(3) 0.049(3) -0.009(2) -0.017(2) 0.004(2) C6 0.057(3) 0.068(3) 0.046(2) -0.013(2) -0.011(2) -0.008(2) C7 0.044(2) 0.043(2) 0.043(2) 0.0029(17) 0.0020(17) 0.0085(17) C8 0.044(2) 0.064(3) 0.062(3) 0.007(2) -0.006(2) 0.010(2) C9 0.048(3) 0.060(3) 0.062(3) 0.005(2) 0.004(2) 0.019(2) Mn1 0.0533(6) 0.0445(5) 0.0392(6) 0.000 0.000 0.0098(4) N1 0.048(2) 0.046(2) 0.0415(19) 0.0000(15) -0.0024(15) 0.0035(15) N2 0.048(2) 0.0425(19) 0.0388(18) -0.0007(16) -0.0044(15) -0.0019(14) N3 0.053(2) 0.055(2) 0.046(2) -0.0060(17) -0.0107(16) 0.0065(18) N4 0.047(2) 0.054(2) 0.0365(18) -0.0083(15) -0.0007(15) -0.0065(16) N5 0.057(2) 0.054(2) 0.049(2) 0.0039(17) 0.0051(19) 0.0159(18) N6 0.049(2) 0.051(2) 0.044(2) 0.0048(16) -0.0039(16) 0.0051(15) O1 0.093(3) 0.098(3) 0.096(3) 0.049(3) -0.044(3) -0.048(3) O2 0.082(2) 0.0461(18) 0.0426(18) 0.0015(14) 0.0075(16) -0.0096(16) S3 0.0554(9) 0.0540(9) 0.0415(11) 0.000 0.000 -0.0155(6) _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 C1 C2 1.350(6) . ? C1 N1 1.371(6) . ? C1 H1 0.9500 . ? C2 N2 1.371(6) . ? C2 H2A 0.9500 . ? C3 N1 1.332(6) . ? C3 N2 1.342(6) . ? C3 C4 1.444(6) . ? C4 N3 1.332(6) . ? C4 N4 1.346(6) . ? C5 C6 1.350(8) . ? C5 N3 1.387(7) . ? C5 H5 0.9500 . ? C6 N4 1.363(6) . ? C6 H6A 0.9500 . ? C7 N6 1.323(6) . ? C7 N5 1.334(6) . ? C7 C7 1.454(9) 7_444 ? C8 N6 1.367(6) . ? C8 C9 1.364(8) . ? C8 H8 0.9500 . ? C9 N5 1.367(7) . ? C9 H9 0.9500 . ? Mn1 N1 2.252(4) 7_444 ? Mn1 N1 2.252(4) . ? Mn1 N3 2.262(4) 7_444 ? Mn1 N3 2.262(4) . ? Mn1 N5 2.260(5) . ? Mn1 N5 2.260(5) 7_444 ? N2 H3A 0.8800 . ? N4 H4 0.8800 . ? N6 H6 0.8800 . ? O1 S3 1.443(5) . ? O2 S3 1.466(4) . ? S3 O1 1.443(5) 7_454 ? S3 O2 1.466(4) 7_454 ? 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 C2 C1 N1 109.7(4) . . ? C2 C1 H1 125.2 . . ? N1 C1 H1 125.2 . . ? N2 C2 C1 106.7(4) . . ? N2 C2 H2A 126.6 . . ? C1 C2 H2A 126.6 . . ? N1 C3 N2 111.2(4) . . ? N1 C3 C4 119.6(4) . . ? N2 C3 C4 129.2(4) . . ? N3 C4 N4 111.3(4) . . ? N3 C4 C3 118.9(4) . . ? N4 C4 C3 129.8(4) . . ? C6 C5 N3 108.8(4) . . ? C6 C5 H5 125.6 . . ? N3 C5 H5 125.6 . . ? C5 C6 N4 107.6(4) . . ? C5 C6 H6A 126.2 . . ? N4 C6 H6A 126.2 . . ? N6 C7 N5 111.8(4) . . ? N6 C7 C7 128.7(3) . 7_444 ? N5 C7 C7 119.5(3) . 7_444 ? N6 C8 C9 105.3(4) . . ? N6 C8 H8 127.3 . . ? C9 C8 H8 127.3 . . ? N5 C9 C8 110.4(4) . . ? N5 C9 H9 124.8 . . ? C8 C9 H9 124.8 . . ? N1 Mn1 N1 97.4(2) 7_444 . ? N1 Mn1 N3 75.05(13) 7_444 7_444 ? N1 Mn1 N3 94.24(14) . 7_444 ? N1 Mn1 N3 94.24(14) 7_444 . ? N1 Mn1 N3 75.05(13) . . ? N3 Mn1 N3 164.0(2) 7_444 . ? N1 Mn1 N5 96.31(14) 7_444 . ? N1 Mn1 N5 158.86(14) . . ? N3 Mn1 N5 104.79(15) 7_444 . ? N3 Mn1 N5 88.00(15) . . ? N1 Mn1 N5 158.86(14) 7_444 7_444 ? N1 Mn1 N5 96.31(14) . 7_444 ? N3 Mn1 N5 88.00(15) 7_444 7_444 ? N3 Mn1 N5 104.79(15) . 7_444 ? N5 Mn1 N5 75.6(2) . 7_444 ? C3 N1 C1 105.5(4) . . ? C3 N1 Mn1 113.0(3) . . ? C1 N1 Mn1 140.9(3) . . ? C3 N2 C2 107.0(4) . . ? C3 N2 H3A 126.5 . . ? C2 N2 H3A 126.5 . . ? C4 N3 C5 105.4(4) . . ? C4 N3 Mn1 113.1(3) . . ? C5 N3 Mn1 141.2(3) . . ? C4 N4 C6 106.9(4) . . ? C4 N4 H4 126.6 . . ? C6 N4 H4 126.6 . . ? C7 N5 C9 104.5(4) . . ? C7 N5 Mn1 112.6(3) . . ? C9 N5 Mn1 142.3(3) . . ? C7 N6 C8 108.0(4) . . ? C7 N6 H6 126.0 . . ? C8 N6 H6 126.0 . . ? O1 S3 O1 107.4(5) . 7_454 ? O1 S3 O2 111.0(3) . . ? O1 S3 O2 108.9(2) 7_454 . ? O1 S3 O2 108.9(2) . 7_454 ? O1 S3 O2 111.0(3) 7_454 7_454 ? O2 S3 O2 109.6(3) . 7_454 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.246 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.077 data_D-5 _database_code_depnum_ccdc_archive 'CCDC 886482' #TrackingRef 'D-5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 Fe N12 O4 S' _chemical_formula_weight 554.35 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M I4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' _cell_length_a 12.8660(3) _cell_length_b 12.8660(3) _cell_length_c 14.3888(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2381.83(11) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.773 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8011 _exptl_absorpt_correction_T_max 0.8607 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11774 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.38 _reflns_number_total 2614 _reflns_number_gt 2424 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+1.0088P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.034(17) _refine_ls_number_reflns 2614 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0790 _refine_ls_wR_factor_gt 0.0767 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.027 _refine_ls_shift/su_mean 0.004 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.5000 0.5000 0.00911(3) 0.04378(13) Uani 1 2 d S . . C1 C 0.4300(2) 0.69810(19) -0.1343(2) 0.0576(7) Uani 1 1 d . . . H1 H 0.4109 0.7494 -0.0921 0.069 Uiso 1 1 calc R . . C2 C 0.4345(2) 0.71071(19) -0.2274(2) 0.0621(7) Uani 1 1 d . . . H2 H 0.4184 0.7707 -0.2604 0.075 Uiso 1 1 calc R . . C3 C 0.48064(18) 0.55272(18) -0.19121(16) 0.0446(5) Uani 1 1 d . . . C4 C 0.41039(19) 0.6718(2) 0.1677(2) 0.0532(6) Uani 1 1 d . . . H4 H 0.4623 0.7221 0.1666 0.064 Uiso 1 1 calc R . . C5 C 0.3275(2) 0.6724(2) 0.22487(19) 0.0565(6) Uani 1 1 d . . . H5 H 0.3122 0.7221 0.2699 0.068 Uiso 1 1 calc R . . C6 C 0.31942(16) 0.53643(17) 0.13468(16) 0.0400(4) Uani 1 1 d . . . C7 C 0.29244(18) 0.44050(17) 0.08673(16) 0.0418(4) Uani 1 1 d . . . C8 C 0.2187(2) 0.3012(2) 0.03267(19) 0.0592(7) Uani 1 1 d . . . H6 H 0.1710 0.2483 0.0212 0.071 Uiso 1 1 calc R . . C9 C 0.3151(2) 0.3117(2) -0.0062(2) 0.0619(7) Uani 1 1 d . . . H9 H 0.3446 0.2660 -0.0488 0.074 Uiso 1 1 calc R . . N1 N 0.45797(17) 0.59792(15) -0.11091(16) 0.0509(5) Uani 1 1 d . . . N2 N 0.46716(17) 0.61805(15) -0.26360(14) 0.0518(5) Uani 1 1 d . . . H2A H 0.4772 0.6041 -0.3214 0.062 Uiso 1 1 calc R . . N3 N 0.40672(15) 0.58556(16) 0.11099(14) 0.0456(4) Uani 1 1 d . . . N4 N 0.26955(15) 0.58540(16) 0.20388(15) 0.0472(4) Uani 1 1 d . . . H4A H 0.2126 0.5662 0.2300 0.057 Uiso 1 1 calc R . . N5 N 0.36183(16) 0.40076(16) 0.02751(14) 0.0502(5) Uani 1 1 d . . . N6 N 0.20609(16) 0.38322(16) 0.09146(14) 0.0477(4) Uani 1 1 d . . . H8 H 0.1525 0.3958 0.1253 0.057 Uiso 1 1 calc R . . O1 O 1.0221(2) 0.4111(2) 0.17801(19) 0.0926(9) Uani 1 1 d . . . O2 O 0.90983(13) 0.47454(18) 0.29597(13) 0.0636(5) Uani 1 1 d . . . S1 S 1.0000 0.5000 0.23698(5) 0.0501(2) Uani 1 2 d S . . 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 Fe1 0.0414(2) 0.0499(3) 0.0401(3) 0.000 0.000 0.00611(19) C1 0.0633(15) 0.0410(12) 0.0684(18) -0.0080(11) -0.0053(12) 0.0132(11) C2 0.0729(17) 0.0420(12) 0.0715(19) 0.0081(12) -0.0081(14) 0.0093(12) C3 0.0483(12) 0.0427(11) 0.0428(12) 0.0007(9) -0.0019(9) 0.0045(10) C4 0.0487(13) 0.0504(13) 0.0603(15) -0.0120(11) 0.0028(11) -0.0091(11) C5 0.0540(14) 0.0572(14) 0.0581(16) -0.0196(11) 0.0058(11) -0.0085(12) C6 0.0382(10) 0.0456(11) 0.0362(10) -0.0007(8) -0.0038(8) 0.0019(9) C7 0.0435(11) 0.0448(11) 0.0372(11) -0.0004(9) -0.0067(8) 0.0031(9) C8 0.0652(16) 0.0570(15) 0.0555(15) -0.0136(11) -0.0143(12) -0.0086(13) C9 0.0652(15) 0.0603(14) 0.0600(16) -0.0230(13) -0.0063(13) -0.0013(12) N1 0.0583(12) 0.0451(10) 0.0493(11) -0.0034(9) -0.0015(9) 0.0117(9) N2 0.0626(12) 0.0466(10) 0.0461(12) 0.0055(8) -0.0036(9) 0.0051(9) N3 0.0432(10) 0.0491(10) 0.0445(10) -0.0059(8) 0.0010(8) 0.0001(8) N4 0.0430(10) 0.0522(11) 0.0464(11) -0.0069(9) 0.0021(8) -0.0036(8) N5 0.0522(10) 0.0537(11) 0.0449(11) -0.0098(8) -0.0042(8) 0.0029(9) N6 0.0482(10) 0.0534(11) 0.0416(10) -0.0025(8) -0.0059(8) -0.0084(9) O1 0.0937(17) 0.0857(16) 0.0985(19) -0.0358(14) 0.0424(14) -0.0348(13) O2 0.0415(9) 0.1020(15) 0.0472(10) -0.0093(10) 0.0010(7) -0.0131(10) S1 0.0482(4) 0.0579(5) 0.0443(6) 0.000 0.000 -0.0124(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 Fe1 N3 2.191(2) 6_554 ? Fe1 N3 2.191(2) . ? Fe1 N1 2.205(2) . ? Fe1 N1 2.205(2) 6_554 ? Fe1 N5 2.205(2) 6_554 ? Fe1 N5 2.205(2) . ? C1 C2 1.350(4) . ? C1 N1 1.380(3) . ? C2 N2 1.368(4) . ? C3 N1 1.326(3) . ? C3 N2 1.350(3) . ? C3 C3 1.445(5) 6_554 ? C4 C5 1.348(4) . ? C4 N3 1.378(3) . ? C5 N4 1.379(3) . ? C6 N3 1.333(3) . ? C6 N4 1.342(3) . ? C6 C7 1.456(3) . ? C7 N5 1.336(3) . ? C7 N6 1.335(3) . ? C8 N6 1.362(3) . ? C8 C9 1.367(4) . ? C9 N5 1.383(3) . ? O1 S1 1.452(2) . ? O2 S1 1.4743(18) . ? S1 O1 1.452(2) 6_654 ? S1 O2 1.4742(18) 6_654 ? 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 N3 Fe1 N3 96.02(11) 6_554 . ? N3 Fe1 N1 160.97(7) 6_554 . ? N3 Fe1 N1 95.89(8) . . ? N3 Fe1 N1 95.89(8) 6_554 6_554 ? N3 Fe1 N1 160.97(7) . 6_554 ? N1 Fe1 N1 76.89(11) . 6_554 ? N3 Fe1 N5 76.64(7) 6_554 6_554 ? N3 Fe1 N5 94.03(8) . 6_554 ? N1 Fe1 N5 87.76(8) . 6_554 ? N1 Fe1 N5 103.13(8) 6_554 6_554 ? N3 Fe1 N5 94.03(8) 6_554 . ? N3 Fe1 N5 76.64(7) . . ? N1 Fe1 N5 103.13(8) . . ? N1 Fe1 N5 87.76(8) 6_554 . ? N5 Fe1 N5 166.20(11) 6_554 . ? C2 C1 N1 110.1(2) . . ? C1 C2 N2 106.6(2) . . ? N1 C3 N2 111.8(2) . . ? N1 C3 C3 119.18(13) . 6_554 ? N2 C3 C3 128.97(14) . 6_554 ? C5 C4 N3 109.8(2) . . ? C4 C5 N4 106.8(2) . . ? N3 C6 N4 111.7(2) . . ? N3 C6 C7 118.8(2) . . ? N4 C6 C7 129.5(2) . . ? N5 C7 N6 112.2(2) . . ? N5 C7 C6 117.9(2) . . ? N6 C7 C6 130.0(2) . . ? N6 C8 C9 106.6(2) . . ? C8 C9 N5 109.4(2) . . ? C3 N1 C1 104.8(2) . . ? C3 N1 Fe1 112.21(15) . . ? C1 N1 Fe1 142.05(18) . . ? C3 N2 C2 106.8(2) . . ? C6 N3 C4 105.03(19) . . ? C6 N3 Fe1 113.22(15) . . ? C4 N3 Fe1 141.43(16) . . ? C6 N4 C5 106.6(2) . . ? C7 N5 C9 104.5(2) . . ? C7 N5 Fe1 113.20(15) . . ? C9 N5 Fe1 142.08(18) . . ? C7 N6 C8 107.3(2) . . ? O1 S1 O1 108.5(3) . 6_654 ? O1 S1 O2 110.93(14) . 6_654 ? O1 S1 O2 108.40(12) 6_654 6_654 ? O1 S1 O2 108.40(12) . . ? O1 S1 O2 110.93(14) 6_654 . ? O2 S1 O2 109.70(15) 6_654 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.38 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.181 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.042 data_D-6 _database_code_depnum_ccdc_archive 'CCDC 886483' #TrackingRef 'D-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N12 O4 S Zn' _chemical_formula_weight 563.87 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M I4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' _cell_length_a 12.783(2) _cell_length_b 12.783(2) _cell_length_c 14.358(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2346.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 1.189 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7168 _exptl_absorpt_correction_T_max 0.8903 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4400 _diffrn_reflns_av_R_equivalents 0.0604 _diffrn_reflns_av_sigmaI/netI 0.0793 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.97 _reflns_number_total 1663 _reflns_number_gt 1134 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment costr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(3) _refine_ls_number_reflns 1663 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0816 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1063 _refine_ls_wR_factor_gt 0.0915 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.974 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 0.5000 0.02200(7) 0.0443(3) Uani 1 2 d S . . N3 N 0.5854(4) 0.4081(4) -0.0790(4) 0.0439(14) Uani 1 1 d . . . N4 N 0.5854(4) 0.2700(4) -0.1723(4) 0.0397(13) Uani 1 1 d . . . H4A H 0.5661 0.2111 -0.1989 0.048 Uiso 1 1 calc R . . N2 N 0.3822(4) 0.2060(4) -0.0588(4) 0.0419(14) Uani 1 1 d . . . H2A H 0.3952 0.1503 -0.0930 0.050 Uiso 1 1 calc R . . N1 N 0.4001(4) 0.3622(4) 0.0045(4) 0.0435(14) Uani 1 1 d . . . N6 N 0.6192(4) 0.4662(4) 0.2924(4) 0.0445(14) Uani 1 1 d . . . H6A H 0.6050 0.4764 0.3517 0.053 Uiso 1 1 calc R . . C9 C 0.5523(5) 0.4803(5) 0.2207(5) 0.0434(17) Uani 1 1 d . . . N5 N 0.5975(4) 0.4569(4) 0.1402(4) 0.0456(14) Uani 1 1 d . . . C6 C 0.6725(5) 0.4130(5) -0.1358(5) 0.0457(18) Uani 1 1 d . . . H6B H 0.7238 0.4667 -0.1348 0.055 Uiso 1 1 calc R . . C1 C 0.3103(5) 0.3151(5) 0.0386(6) 0.0534(19) Uani 1 1 d . . . H1A H 0.2637 0.3456 0.0824 0.064 Uiso 1 1 calc R . . C5 C 0.6731(5) 0.3285(5) -0.1931(5) 0.0481(18) Uani 1 1 d . . . H5A H 0.7243 0.3127 -0.2390 0.058 Uiso 1 1 calc R . . C2 C 0.2989(5) 0.2191(6) 0.0003(5) 0.0512(19) Uani 1 1 d . . . H2B H 0.2443 0.1705 0.0121 0.061 Uiso 1 1 calc R . . C3 C 0.4393(5) 0.2919(5) -0.0554(5) 0.0388(16) Uani 1 1 d . . . C4 C 0.5354(5) 0.3206(5) -0.1034(5) 0.0379(15) Uani 1 1 d . . . C7 C 0.6972(6) 0.4282(5) 0.1628(5) 0.0502(19) Uani 1 1 d . . . H7A H 0.7488 0.4073 0.1190 0.060 Uiso 1 1 calc R . . C8 C 0.7127(5) 0.4333(5) 0.2570(6) 0.0526(19) Uani 1 1 d . . . H8A H 0.7748 0.4175 0.2904 0.063 Uiso 1 1 calc R . . S1 S 0.0000 0.0000 0.04388(19) 0.0488(8) Uani 1 2 d S . . O2 O 0.0916(3) -0.0224(4) -0.0158(3) 0.0517(13) Uani 1 1 d . . . O1 O 0.0216(4) 0.0910(4) 0.1030(4) 0.0788(18) 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 Zn1 0.0511(8) 0.0447(7) 0.0371(7) 0.000 0.000 0.0066(6) N3 0.041(3) 0.049(4) 0.041(4) 0.004(3) 0.003(3) 0.005(3) N4 0.046(3) 0.033(3) 0.040(3) -0.005(3) 0.002(3) -0.005(2) N2 0.053(4) 0.043(3) 0.029(3) 0.004(3) 0.000(3) -0.005(3) N1 0.049(3) 0.044(3) 0.037(4) 0.005(3) 0.008(3) 0.009(3) N6 0.047(3) 0.052(3) 0.034(4) 0.006(3) -0.002(3) 0.004(3) C9 0.040(4) 0.047(4) 0.043(5) 0.002(3) -0.001(3) 0.004(3) N5 0.037(3) 0.052(4) 0.049(4) -0.004(3) 0.006(3) 0.010(3) C6 0.043(4) 0.046(4) 0.049(5) -0.002(4) 0.006(3) -0.003(4) C1 0.056(4) 0.057(5) 0.047(5) 0.008(4) 0.015(4) 0.004(4) C5 0.048(4) 0.048(4) 0.048(5) -0.003(3) 0.005(3) -0.001(3) C2 0.049(4) 0.055(5) 0.050(5) 0.011(4) 0.008(4) -0.001(3) C3 0.047(4) 0.039(4) 0.031(4) 0.006(3) -0.001(3) 0.001(3) C4 0.045(4) 0.033(4) 0.035(4) 0.005(3) 0.000(3) 0.001(3) C7 0.045(5) 0.057(5) 0.048(5) 0.002(4) 0.006(4) 0.008(4) C8 0.038(4) 0.059(4) 0.061(6) 0.008(4) -0.003(4) 0.008(3) S1 0.0464(15) 0.0513(16) 0.049(2) 0.000 0.000 0.0106(13) O2 0.039(3) 0.074(3) 0.042(3) 0.004(3) 0.000(2) 0.010(2) O1 0.093(4) 0.071(4) 0.072(4) -0.028(3) -0.030(3) 0.028(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 Zn1 N3 2.162(6) . ? Zn1 N3 2.162(6) 6_554 ? Zn1 N5 2.176(6) . ? Zn1 N5 2.176(6) 6_554 ? Zn1 N1 2.190(5) . ? Zn1 N1 2.190(5) 6_554 ? N3 C4 1.334(8) . ? N3 C6 1.382(8) . ? N4 C4 1.344(8) . ? N4 C5 1.380(8) . ? N4 H4A 0.8800 . ? N2 C3 1.319(8) . ? N2 C2 1.372(8) . ? N2 H2A 0.8800 . ? N1 C3 1.341(8) . ? N1 C1 1.385(8) . ? N6 C9 1.351(8) . ? N6 C8 1.365(8) . ? N6 H6A 0.8800 . ? C9 N5 1.327(9) . ? C9 C9 1.429(12) 6_554 ? N5 C7 1.365(8) . ? C6 C5 1.358(9) . ? C6 H6B 0.9500 . ? C1 C2 1.352(9) . ? C1 H1A 0.9500 . ? C5 H5A 0.9500 . ? C2 H2B 0.9500 . ? C3 C4 1.456(9) . ? C7 C8 1.368(11) . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? S1 O1 1.466(6) . ? S1 O1 1.466(6) 6_444 ? S1 O2 1.479(5) 6_444 ? S1 O2 1.479(5) . ? 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 N3 Zn1 N3 95.8(3) . 6_554 ? N3 Zn1 N5 95.5(2) . . ? N3 Zn1 N5 161.7(2) 6_554 . ? N3 Zn1 N5 161.7(2) . 6_554 ? N3 Zn1 N5 95.5(2) 6_554 6_554 ? N5 Zn1 N5 77.6(3) . 6_554 ? N3 Zn1 N1 77.3(2) . . ? N3 Zn1 N1 93.8(2) 6_554 . ? N5 Zn1 N1 102.7(2) . . ? N5 Zn1 N1 87.7(2) 6_554 . ? N3 Zn1 N1 93.8(2) . 6_554 ? N3 Zn1 N1 77.3(2) 6_554 6_554 ? N5 Zn1 N1 87.7(2) . 6_554 ? N5 Zn1 N1 102.7(2) 6_554 6_554 ? N1 Zn1 N1 166.8(3) . 6_554 ? C4 N3 C6 105.6(6) . . ? C4 N3 Zn1 112.9(4) . . ? C6 N3 Zn1 141.1(5) . . ? C4 N4 C5 106.6(5) . . ? C4 N4 H4A 126.7 . . ? C5 N4 H4A 126.7 . . ? C3 N2 C2 107.7(6) . . ? C3 N2 H2A 126.1 . . ? C2 N2 H2A 126.1 . . ? C3 N1 C1 104.2(6) . . ? C3 N1 Zn1 113.2(4) . . ? C1 N1 Zn1 142.4(5) . . ? C9 N6 C8 108.1(6) . . ? C9 N6 H6A 125.9 . . ? C8 N6 H6A 125.9 . . ? N5 C9 N6 111.0(6) . . ? N5 C9 C9 119.2(4) . 6_554 ? N6 C9 C9 129.7(4) . 6_554 ? C9 N5 C7 105.0(6) . . ? C9 N5 Zn1 111.9(4) . . ? C7 N5 Zn1 142.1(5) . . ? C5 C6 N3 109.0(6) . . ? C5 C6 H6B 125.5 . . ? N3 C6 H6B 125.5 . . ? C2 C1 N1 109.9(6) . . ? C2 C1 H1A 125.0 . . ? N1 C1 H1A 125.0 . . ? C6 C5 N4 107.1(6) . . ? C6 C5 H5A 126.4 . . ? N4 C5 H5A 126.4 . . ? C1 C2 N2 106.2(6) . . ? C1 C2 H2B 126.9 . . ? N2 C2 H2B 126.9 . . ? N2 C3 N1 112.0(6) . . ? N2 C3 C4 131.2(6) . . ? N1 C3 C4 116.7(6) . . ? N3 C4 N4 111.6(6) . . ? N3 C4 C3 119.4(6) . . ? N4 C4 C3 129.0(6) . . ? N5 C7 C8 111.0(7) . . ? N5 C7 H7A 124.5 . . ? C8 C7 H7A 124.5 . . ? N6 C8 C7 104.9(6) . . ? N6 C8 H8A 127.6 . . ? C7 C8 H8A 127.6 . . ? O1 S1 O1 109.2(5) . 6_444 ? O1 S1 O2 109.3(3) . 6_444 ? O1 S1 O2 109.9(3) 6_444 6_444 ? O1 S1 O2 109.9(3) . . ? O1 S1 O2 109.3(3) 6_444 . ? O2 S1 O2 109.2(4) 6_444 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N6 H6A O2 0.88 1.91 2.780(7) 169.3 5 N2 H2A O1 0.88 1.83 2.697(8) 169.3 7_544 N4 H4A O2 0.88 1.89 2.766(7) 175.0 7_544 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.430 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.071 data_L-1 _database_code_depnum_ccdc_archive 'CCDC 886484' #TrackingRef 'L-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N12 O4 Ru S' _chemical_formula_weight 599.57 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M I4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' _cell_length_a 12.5812(8) _cell_length_b 12.5812(8) _cell_length_c 14.2715(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2259.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.763 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.842 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8841 _exptl_absorpt_correction_T_max 0.9591 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4338 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.97 _reflns_number_total 1488 _reflns_number_gt 1393 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0912P)^2^+52.2218P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment contr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(15) _refine_ls_number_reflns 1488 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0706 _refine_ls_wR_factor_ref 0.1932 _refine_ls_wR_factor_gt 0.1910 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.128 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ru1 Ru 0.5000 0.5000 0.11440(8) 0.0188(2) Uani 1 2 d S . . C1 C 0.4228(9) 0.3344(9) 0.2757(9) 0.037(3) Uani 1 1 d . . . H1 H 0.4778 0.2827 0.2729 0.045 Uiso 1 1 calc R . . C2 C 0.3404(9) 0.3326(9) 0.3352(9) 0.038(3) Uani 1 1 d . . . H2 H 0.3281 0.2810 0.3826 0.045 Uiso 1 1 calc R . . C3 C 0.3239(8) 0.4684(11) 0.2440(8) 0.038(3) Uani 1 1 d . . . C4 C 0.2960(9) 0.5581(9) 0.1931(9) 0.034(3) Uani 1 1 d . . . C5 C 0.2221(9) 0.7003(9) 0.1316(8) 0.036(3) Uani 1 1 d . . . H5 H 0.1748 0.7573 0.1186 0.043 Uiso 1 1 calc R . . C6 C 0.3192(8) 0.6813(8) 0.0895(9) 0.037(3) Uani 1 1 d . . . H6 H 0.3490 0.7239 0.0411 0.044 Uiso 1 1 calc R . . C7 C 0.4185(9) 0.3068(9) -0.0162(10) 0.038(3) Uani 1 1 d . . . H7 H 0.4007 0.2565 0.0309 0.046 Uiso 1 1 calc R . . C8 C 0.4215(7) 0.2849(8) -0.1047(9) 0.032(3) Uani 1 1 d . . . H8 H 0.4017 0.2196 -0.1334 0.038 Uiso 1 1 calc R . . C9 C 0.4782(10) 0.4499(9) -0.0817(8) 0.038(3) Uani 1 1 d . . . N1 N 0.4154(7) 0.4223(8) 0.2195(7) 0.030(2) Uani 1 1 d . . . N2 N 0.2799(6) 0.4146(7) 0.3164(7) 0.029(2) Uani 1 1 d . . . H3 H 0.2208 0.4317 0.3458 0.034 Uiso 1 1 calc R . . N3 N 0.3665(7) 0.5936(8) 0.1265(8) 0.040(2) Uani 1 1 d . . . N4 N 0.2080(7) 0.6231(8) 0.1935(7) 0.034(2) Uani 1 1 d . . . H4 H 0.1516 0.6148 0.2292 0.040 Uiso 1 1 calc R . . N5 N 0.4436(7) 0.4095(8) 0.0019(8) 0.035(2) Uani 1 1 d . . . N6 N 0.4608(8) 0.3785(7) -0.1514(8) 0.041(3) Uani 1 1 d . . . H9 H 0.4712 0.3875 -0.2119 0.050 Uiso 1 1 calc R . . O1 O 0.5177(8) 0.5944(7) 0.6556(6) 0.046(2) Uani 1 1 d . . . O2 O 0.4068(6) 0.5207(8) 0.5352(7) 0.050(3) Uani 1 1 d . . . S1 S 0.5000 0.5000 0.5951(2) 0.0254(12) Uani 1 2 d S . . 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 Ru1 0.0194(5) 0.0206(5) 0.0163(4) 0.000 0.000 -0.0017(5) C1 0.045(6) 0.026(5) 0.041(7) 0.000(5) 0.008(6) 0.004(5) C2 0.042(6) 0.031(5) 0.040(7) 0.010(5) 0.000(5) 0.001(5) C3 0.021(5) 0.075(8) 0.019(5) -0.016(6) -0.003(4) 0.003(5) C4 0.031(5) 0.042(6) 0.030(6) -0.005(5) -0.013(5) -0.001(5) C5 0.040(5) 0.040(6) 0.028(6) 0.001(5) -0.015(5) 0.012(5) C6 0.029(5) 0.028(5) 0.054(8) 0.013(5) -0.019(5) -0.006(4) C7 0.050(6) 0.028(5) 0.038(7) 0.007(5) -0.011(6) 0.011(5) C8 0.019(4) 0.017(4) 0.059(8) -0.011(5) -0.005(5) -0.001(4) C9 0.062(7) 0.030(5) 0.023(6) -0.001(5) 0.002(6) -0.005(6) N1 0.023(4) 0.044(5) 0.022(4) 0.001(4) -0.004(4) -0.015(4) N2 0.019(4) 0.030(4) 0.038(5) 0.004(4) 0.000(4) -0.002(3) N3 0.039(5) 0.049(5) 0.031(6) -0.008(5) -0.010(5) 0.014(4) N4 0.020(4) 0.053(6) 0.027(5) 0.001(5) 0.002(4) -0.004(4) N5 0.035(5) 0.037(5) 0.034(5) 0.009(4) -0.007(4) -0.004(4) N6 0.045(5) 0.042(5) 0.038(6) -0.009(5) -0.007(5) 0.000(4) O1 0.075(6) 0.041(5) 0.022(4) -0.001(4) -0.017(4) 0.004(4) O2 0.026(4) 0.081(7) 0.044(5) 0.016(5) -0.013(4) -0.013(4) S1 0.0252(15) 0.0272(16) 0.024(3) 0.000 0.000 -0.0029(14) _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 Ru1 N3 2.059(9) 6_554 ? Ru1 N3 2.059(9) . ? Ru1 N1 2.083(9) 6_554 ? Ru1 N1 2.083(9) . ? Ru1 N5 2.092(11) . ? Ru1 N5 2.092(11) 6_554 ? C1 C2 1.340(17) . ? C1 N1 1.369(15) . ? C2 N2 1.310(14) . ? C3 N1 1.335(14) . ? C3 N2 1.354(15) . ? C3 C4 1.388(18) . ? C4 N3 1.374(16) . ? C4 N4 1.377(15) . ? C5 N4 1.325(15) . ? C5 C6 1.383(16) . ? C6 N3 1.360(14) . ? C7 C8 1.295(19) . ? C7 N5 1.355(15) . ? C8 N6 1.441(15) . ? C9 N6 1.358(15) . ? C9 N5 1.368(16) . ? C9 C9 1.37(2) 6_554 ? O1 S1 1.485(9) . ? O2 S1 1.475(9) . ? S1 O2 1.475(9) 6_554 ? S1 O1 1.485(9) 6_554 ? 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 N3 Ru1 N3 170.4(6) 6_554 . ? N3 Ru1 N1 77.9(4) 6_554 6_554 ? N3 Ru1 N1 95.0(4) . 6_554 ? N3 Ru1 N1 95.0(4) 6_554 . ? N3 Ru1 N1 77.9(4) . . ? N1 Ru1 N1 87.9(5) 6_554 . ? N3 Ru1 N5 91.7(4) 6_554 . ? N3 Ru1 N5 95.7(4) . . ? N1 Ru1 N5 168.9(4) 6_554 . ? N1 Ru1 N5 97.1(4) . . ? N3 Ru1 N5 95.7(4) 6_554 6_554 ? N3 Ru1 N5 91.7(4) . 6_554 ? N1 Ru1 N5 97.1(4) 6_554 6_554 ? N1 Ru1 N5 168.9(4) . 6_554 ? N5 Ru1 N5 79.8(5) . 6_554 ? C2 C1 N1 109.4(10) . . ? N2 C2 C1 107.9(10) . . ? N1 C3 N2 109.6(11) . . ? N1 C3 C4 115.7(11) . . ? N2 C3 C4 134.7(10) . . ? N3 C4 N4 109.2(10) . . ? N3 C4 C3 117.6(10) . . ? N4 C4 C3 133.2(11) . . ? N4 C5 C6 106.3(9) . . ? N3 C6 C5 110.9(10) . . ? C8 C7 N5 112.5(11) . . ? C7 C8 N6 106.7(10) . . ? N6 C9 N5 110.0(10) . . ? N6 C9 C9 132.1(7) . 6_554 ? N5 C9 C9 117.9(7) . 6_554 ? C3 N1 C1 104.9(10) . . ? C3 N1 Ru1 115.2(8) . . ? C1 N1 Ru1 139.9(8) . . ? C2 N2 C3 108.2(9) . . ? C6 N3 C4 104.5(9) . . ? C6 N3 Ru1 142.0(9) . . ? C4 N3 Ru1 113.5(8) . . ? C5 N4 C4 109.0(10) . . ? C7 N5 C9 105.2(11) . . ? C7 N5 Ru1 138.1(9) . . ? C9 N5 Ru1 111.1(7) . . ? C9 N6 C8 104.9(10) . . ? O2 S1 O2 109.1(8) . 6_554 ? O2 S1 O1 111.0(6) . 6_554 ? O2 S1 O1 108.4(6) 6_554 6_554 ? O2 S1 O1 108.4(6) . . ? O2 S1 O1 111.0(6) 6_554 . ? O1 S1 O1 109.0(7) 6_554 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H3 O1 0.88 1.91 2.791(12) 174.7 4_464 N4 H4 O2 0.88 1.85 2.722(14) 170.2 4_464 N6 H9 O1 0.88 1.91 2.788(14) 175.6 6_553 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.122 _refine_diff_density_min -0.660 _refine_diff_density_rms 0.178 data_L-2 _database_code_depnum_ccdc_archive 'CCDC 886485' #TrackingRef 'L-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 Co N12 O4 S' _chemical_formula_weight 557.43 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' Co Co 0.3494 0.9721 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M I4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x+1/2, z+1/4' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-y+1/2, x+1, z+3/4' '-x+1, -y+1, z+1' 'y+1, -x+1/2, z+5/4' _cell_length_a 12.7455(4) _cell_length_b 12.7455(4) _cell_length_c 14.2641(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2317.17(18) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.598 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1140 _exptl_absorpt_coefficient_mu 0.885 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6660 _exptl_absorpt_correction_T_max 0.7772 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4511 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1987 _reflns_number_gt 1890 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.024(15) _refine_ls_number_reflns 1987 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0795 _refine_ls_wR_factor_gt 0.0774 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1977(2) 0.4267(2) -0.0792(2) 0.0339(6) Uani 1 1 d . . . H1A H 0.2492 0.4056 -0.0349 0.041 Uiso 1 1 calc R . . C2 C 0.2130(2) 0.4320(2) -0.1734(2) 0.0336(6) Uani 1 1 d . . . H2A H 0.2754 0.4154 -0.2066 0.040 Uiso 1 1 calc R . . C3 C 0.0535(2) 0.47971(19) -0.13942(18) 0.0306(6) Uani 1 1 d . . . C4 C 0.19996(19) 0.7790(2) 0.08070(19) 0.0358(6) Uani 1 1 d . . . H4A H 0.2551 0.8272 0.0687 0.043 Uiso 1 1 calc R . . C5 C 0.1883(2) 0.6828(2) 0.0412(2) 0.0369(6) Uani 1 1 d . . . H5 H 0.2343 0.6521 -0.0034 0.044 Uiso 1 1 calc R . . C6 C 0.05901(18) 0.7056(2) 0.13679(18) 0.0255(5) Uani 1 1 d . . . C7 C -0.03658(18) 0.67843(18) 0.18537(17) 0.0230(5) Uani 1 1 d . . . C8 C -0.17405(19) 0.66945(19) 0.27635(18) 0.0275(5) Uani 1 1 d . . . H8 H -0.2254 0.6849 0.3226 0.033 Uiso 1 1 calc R . . C9 C -0.1725(2) 0.58517(19) 0.21852(19) 0.0273(5) Uani 1 1 d . . . H9 H -0.2235 0.5308 0.2176 0.033 Uiso 1 1 calc R . . Co1 Co 0.0000 0.5000 0.05984(3) 0.02730(15) Uani 1 2 d S . . N1 N 0.09683(17) 0.45648(18) -0.05721(17) 0.0327(5) Uani 1 1 d . . . N2 N 0.11964(17) 0.46598(17) -0.21096(15) 0.0323(5) Uani 1 1 d . . . H2 H 0.1061 0.4767 -0.2707 0.039 Uiso 1 1 d R . . N3 N 0.09837(16) 0.63688(16) 0.07650(16) 0.0306(5) Uani 1 1 d . . . N4 N 0.11800(16) 0.79356(18) 0.14077(15) 0.0289(5) Uani 1 1 d . . . H4 H 0.1059 0.8494 0.1754 0.035 Uiso 1 1 calc R . . N5 N -0.08570(16) 0.59035(16) 0.16129(15) 0.0253(4) Uani 1 1 d . . . N6 N -0.08654(14) 0.72831(15) 0.25502(15) 0.0244(4) Uani 1 1 d . . . H6 H -0.0672 0.7873 0.2820 0.029 Uiso 1 1 calc R . . O1 O 0.09093(19) -0.02167(19) 0.22809(17) 0.0640(8) Uani 1 1 d . . . O2 O 0.02358(15) 0.09189(14) 0.34718(13) 0.0344(4) Uani 1 1 d . . . S1 S 0.0000 0.0000 0.28715(6) 0.0354(3) Uani 1 2 d S . . 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 C1 0.0324(14) 0.0359(14) 0.0334(16) 0.0026(11) -0.0013(12) 0.0159(11) C2 0.0355(14) 0.0347(14) 0.0307(15) 0.0011(11) 0.0041(12) 0.0094(10) C3 0.0334(14) 0.0342(14) 0.0242(13) -0.0036(10) 0.0009(11) 0.0130(11) C4 0.0262(13) 0.0537(17) 0.0277(13) 0.0159(13) 0.0045(11) 0.0003(11) C5 0.0304(13) 0.0528(17) 0.0276(14) 0.0107(13) 0.0093(12) 0.0090(11) C6 0.0236(12) 0.0327(13) 0.0202(12) 0.0074(10) -0.0010(10) 0.0056(9) C7 0.0258(12) 0.0262(12) 0.0171(11) 0.0026(9) -0.0025(9) 0.0044(9) C8 0.0256(12) 0.0275(12) 0.0293(14) -0.0006(10) 0.0085(10) -0.0019(9) C9 0.0298(13) 0.0231(12) 0.0292(13) 0.0016(10) 0.0035(11) -0.0007(10) Co1 0.0318(3) 0.0307(3) 0.0194(3) 0.000 0.000 0.01109(19) N1 0.0369(12) 0.0377(12) 0.0236(11) 0.0016(9) -0.0008(10) 0.0164(10) N2 0.0398(12) 0.0356(12) 0.0216(12) -0.0008(9) 0.0036(10) 0.0119(9) N3 0.0305(11) 0.0365(11) 0.0248(11) 0.0058(9) 0.0060(9) 0.0093(9) N4 0.0287(11) 0.0372(12) 0.0208(10) 0.0060(9) 0.0001(9) -0.0030(9) N5 0.0270(10) 0.0264(11) 0.0225(10) 0.0016(8) 0.0014(8) 0.0039(8) N6 0.0268(10) 0.0226(10) 0.0239(11) 0.0009(9) 0.0013(9) 0.0003(8) O1 0.0742(17) 0.0683(16) 0.0496(15) -0.0297(13) 0.0302(13) -0.0486(13) O2 0.0478(11) 0.0307(10) 0.0246(10) 0.0025(8) 0.0033(8) -0.0122(8) S1 0.0459(5) 0.0407(5) 0.0197(6) 0.000 0.000 -0.0236(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 C1 C2 1.359(4) . ? C1 N1 1.377(3) . ? C1 H1A 0.9500 . ? C2 N2 1.375(3) . ? C2 H2A 0.9500 . ? C3 N1 1.330(3) . ? C3 N2 1.335(3) . ? C3 C3 1.458(5) 7_454 ? C4 C5 1.358(4) . ? C4 N4 1.364(3) . ? C4 H4A 0.9500 . ? C5 N3 1.381(3) . ? C5 H5 0.9500 . ? C6 N3 1.326(3) . ? C6 N4 1.351(3) . ? C6 C7 1.444(3) . ? C7 N5 1.331(3) . ? C7 N6 1.340(3) . ? C8 C9 1.354(4) . ? C8 N6 1.378(3) . ? C8 H8 0.9500 . ? C9 N5 1.376(3) . ? C9 H9 0.9500 . ? Co1 N5 2.148(2) . ? Co1 N5 2.148(2) 7_454 ? Co1 N1 2.149(2) 7_454 ? Co1 N1 2.149(2) . ? Co1 N3 2.161(2) . ? Co1 N3 2.161(2) 7_454 ? N2 H2 0.8801 . ? N4 H4 0.8800 . ? N6 H6 0.8800 . ? O1 S1 1.459(2) . ? O2 S1 1.4816(19) . ? S1 O1 1.459(2) 7_444 ? S1 O2 1.4816(19) 7_444 ? 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 C2 C1 N1 110.2(2) . . ? C2 C1 H1A 124.9 . . ? N1 C1 H1A 124.9 . . ? C1 C2 N2 106.1(2) . . ? C1 C2 H2A 127.0 . . ? N2 C2 H2A 127.0 . . ? N1 C3 N2 112.5(2) . . ? N1 C3 C3 117.86(15) . 7_454 ? N2 C3 C3 129.56(14) . 7_454 ? C5 C4 N4 107.5(2) . . ? C5 C4 H4A 126.3 . . ? N4 C4 H4A 126.3 . . ? C4 C5 N3 108.8(2) . . ? C4 C5 H5 125.6 . . ? N3 C5 H5 125.6 . . ? N3 C6 N4 111.4(2) . . ? N3 C6 C7 118.2(2) . . ? N4 C6 C7 130.4(2) . . ? N5 C7 N6 111.6(2) . . ? N5 C7 C6 118.4(2) . . ? N6 C7 C6 130.0(2) . . ? C9 C8 N6 106.6(2) . . ? C9 C8 H8 126.7 . . ? N6 C8 H8 126.7 . . ? C8 C9 N5 109.6(2) . . ? C8 C9 H9 125.2 . . ? N5 C9 H9 125.2 . . ? N5 Co1 N5 95.29(11) . 7_454 ? N5 Co1 N1 95.33(8) . 7_454 ? N5 Co1 N1 162.53(8) 7_454 7_454 ? N5 Co1 N1 162.53(8) . . ? N5 Co1 N1 95.33(8) 7_454 . ? N1 Co1 N1 78.04(12) 7_454 . ? N5 Co1 N3 77.77(8) . . ? N5 Co1 N3 93.65(8) 7_454 . ? N1 Co1 N3 102.13(9) 7_454 . ? N1 Co1 N3 87.74(8) . . ? N5 Co1 N3 93.65(8) . 7_454 ? N5 Co1 N3 77.77(8) 7_454 7_454 ? N1 Co1 N3 87.74(8) 7_454 7_454 ? N1 Co1 N3 102.13(9) . 7_454 ? N3 Co1 N3 167.38(12) . 7_454 ? C3 N1 C1 104.4(2) . . ? C3 N1 Co1 112.90(16) . . ? C1 N1 Co1 141.7(2) . . ? C3 N2 C2 106.8(2) . . ? C3 N2 H2 126.6 . . ? C2 N2 H2 126.6 . . ? C6 N3 C5 105.7(2) . . ? C6 N3 Co1 112.65(16) . . ? C5 N3 Co1 141.51(19) . . ? C6 N4 C4 106.7(2) . . ? C6 N4 H4 126.7 . . ? C4 N4 H4 126.7 . . ? C7 N5 C9 105.4(2) . . ? C7 N5 Co1 112.77(16) . . ? C9 N5 Co1 141.50(17) . . ? C7 N6 C8 106.9(2) . . ? C7 N6 H6 126.6 . . ? C8 N6 H6 126.6 . . ? O1 S1 O1 109.5(2) 7_444 . ? O1 S1 O2 110.19(13) 7_444 . ? O1 S1 O2 108.80(10) . . ? O1 S1 O2 108.80(10) 7_444 7_444 ? O1 S1 O2 110.19(13) . 7_444 ? O2 S1 O2 109.39(15) . 7_444 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.317 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.045 data_L-3 _database_code_depnum_ccdc_archive 'CCDC 886486' #TrackingRef 'L-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 N10 Ni O4 S' _chemical_formula_weight 553.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M I4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x+1/2, z+1/4' '-x, -y, z' 'y, -x+1/2, z+1/4' 'x+1/2, y+1/2, z+1/2' '-y+1/2, x+1, z+3/4' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1, z+3/4' _cell_length_a 12.6871(3) _cell_length_b 12.6871(3) _cell_length_c 14.2044(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2286.37(10) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 2.534 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6312 _exptl_absorpt_correction_T_max 0.6312 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5083 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.67 _diffrn_reflns_theta_max 60.90 _reflns_number_total 1715 _reflns_number_gt 1632 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.10(5) _refine_ls_number_reflns 1715 _refine_ls_number_parameters 192 _refine_ls_number_restraints 115 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1355 _refine_ls_wR_factor_gt 0.1322 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.089 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 1.0000 0.5000 0.25220(7) 0.0212(3) Uani 1 2 d SU . . C1 C 0.8037(3) 0.5783(3) 0.1171(4) 0.0280(10) Uani 1 1 d U . . H1 H 0.7539 0.5994 0.1613 0.034 Uiso 1 1 calc R . . C2 C 0.7873(4) 0.5727(4) 0.0224(4) 0.0290(10) Uani 1 1 d U . . C3 C 0.9466(4) 0.5221(3) 0.0554(3) 0.0217(9) Uani 1 1 d U . . C4 C 0.8297(4) 0.5796(4) 0.4123(3) 0.0252(10) Uani 1 1 d U . . C5 C 0.8281(4) 0.6643(4) 0.4705(3) 0.0274(10) Uani 1 1 d U . . C6 C 0.9646(3) 0.6759(3) 0.3779(3) 0.0215(9) Uani 1 1 d U . . C7 C 1.0595(3) 0.7041(3) 0.3273(3) 0.0211(9) Uani 1 1 d U . . C8 C 1.1997(4) 0.7776(4) 0.2690(3) 0.0283(11) Uani 1 1 d U . . C9 C 1.1865(4) 0.6813(4) 0.2285(3) 0.0286(10) Uani 1 1 d U . . H2 H 0.732(4) 0.582(4) -0.016(4) 0.023(12) Uiso 1 1 d . . . H3 H 0.897(4) 0.524(4) -0.080(4) 0.037(15) Uiso 1 1 d . . . H4 H 0.779(4) 0.518(4) 0.411(3) 0.016(11) Uiso 1 1 d . . . H5 H 0.785(5) 0.685(5) 0.521(5) 0.047(18) Uiso 1 1 d . . . H7 H 1.111(5) 0.852(5) 0.358(5) 0.05(2) Uiso 1 1 d . . . H8 H 1.250(4) 0.830(4) 0.266(4) 0.025(13) Uiso 1 1 d . . . H9 H 1.226(4) 0.645(4) 0.184(4) 0.024(12) Uiso 1 1 d . . . N1 N 0.9052(3) 0.5479(3) 0.1372(3) 0.0251(8) Uani 1 1 d U . . N2 N 0.8793(3) 0.5363(3) -0.0164(3) 0.0250(8) Uani 1 1 d U . . N3 N 0.9161(3) 0.5866(3) 0.3539(3) 0.0223(8) Uani 1 1 d U . . N4 N 0.9150(3) 0.7250(3) 0.4485(3) 0.0231(8) Uani 1 1 d U . . H6 H 0.9335 0.7830 0.4750 0.028 Uiso 1 1 calc R . . N5 N 1.0968(3) 0.6344(3) 0.2658(3) 0.0245(8) Uani 1 1 d U . . N6 N 1.1191(3) 0.7915(3) 0.3313(3) 0.0246(9) Uani 1 1 d U . . O1 O 1.0228(3) 0.5913(3) 0.6712(3) 0.0433(10) Uani 1 1 d U . . O2 O 0.9075(2) 0.5236(3) 0.7907(2) 0.0312(8) Uani 1 1 d U . . S1 S 1.0000 0.5000 0.72997(11) 0.0247(4) Uani 1 2 d SU . . 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 0.0247(6) 0.0212(5) 0.0177(6) 0.000 0.000 0.0024(4) C1 0.019(2) 0.027(2) 0.037(3) 0.001(2) 0.003(2) 0.0060(17) C2 0.025(2) 0.029(2) 0.033(3) 0.001(2) -0.003(2) 0.0033(19) C3 0.022(2) 0.022(2) 0.021(3) 0.0011(17) -0.0001(19) 0.0005(17) C4 0.025(2) 0.027(2) 0.024(2) 0.0000(18) 0.0050(18) -0.003(2) C5 0.027(2) 0.028(2) 0.028(3) -0.0013(18) 0.008(2) -0.0016(18) C6 0.025(2) 0.025(2) 0.014(2) 0.0027(18) 0.0005(17) 0.0010(17) C7 0.022(2) 0.026(2) 0.015(2) 0.0045(18) -0.0028(17) 0.0007(17) C8 0.027(2) 0.032(3) 0.025(3) 0.008(2) 0.0018(19) -0.007(2) C9 0.025(2) 0.036(3) 0.025(2) 0.006(2) 0.007(2) 0.0030(19) N1 0.028(2) 0.0230(19) 0.025(2) 0.0006(16) 0.0030(17) 0.0044(15) N2 0.0252(19) 0.028(2) 0.022(2) 0.0031(16) -0.0019(17) 0.0015(15) N3 0.0247(19) 0.0223(19) 0.0199(19) 0.0030(15) 0.0020(15) 0.0001(15) N4 0.0263(19) 0.0225(18) 0.020(2) -0.0034(16) 0.0009(16) -0.0023(14) N5 0.027(2) 0.0236(19) 0.023(2) 0.0016(15) 0.0032(15) 0.0030(16) N6 0.029(2) 0.026(2) 0.019(2) 0.0043(17) 0.0004(15) -0.0029(16) O1 0.045(2) 0.043(2) 0.041(2) 0.0156(18) 0.0178(17) 0.0157(17) O2 0.0221(17) 0.047(2) 0.0247(18) 0.0044(15) 0.0034(13) 0.0058(15) S1 0.0245(8) 0.0305(8) 0.0191(11) 0.000 0.000 0.0060(6) _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 N3 2.104(4) 3_765 ? Ni1 N3 2.104(4) . ? Ni1 N5 2.111(4) . ? Ni1 N5 2.111(4) 3_765 ? Ni1 N1 2.118(4) . ? Ni1 N1 2.118(4) 3_765 ? C1 C2 1.363(8) . ? C1 N1 1.373(6) . ? C2 N2 1.371(6) . ? C3 N1 1.317(6) . ? C3 N2 1.342(6) . ? C3 C3 1.466(9) 3_765 ? C4 C5 1.356(7) . ? C4 N3 1.377(6) . ? C5 N4 1.380(6) . ? C6 N3 1.333(6) . ? C6 N4 1.338(6) . ? C6 C7 1.448(6) . ? C7 N5 1.330(6) . ? C7 N6 1.342(6) . ? C8 C9 1.361(8) . ? C8 N6 1.364(6) . ? C9 N5 1.389(6) . ? O1 S1 1.458(4) . ? O2 S1 1.486(3) . ? S1 O1 1.458(4) 3_765 ? S1 O2 1.486(3) 3_765 ? 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 N3 Ni1 N3 93.3(2) 3_765 . ? N3 Ni1 N5 93.70(14) 3_765 . ? N3 Ni1 N5 79.04(14) . . ? N3 Ni1 N5 79.04(14) 3_765 3_765 ? N3 Ni1 N5 93.70(14) . 3_765 ? N5 Ni1 N5 169.5(2) . 3_765 ? N3 Ni1 N1 165.20(14) 3_765 . ? N3 Ni1 N1 95.30(14) . . ? N5 Ni1 N1 99.76(14) . . ? N5 Ni1 N1 88.37(14) 3_765 . ? N3 Ni1 N1 95.30(14) 3_765 3_765 ? N3 Ni1 N1 165.20(14) . 3_765 ? N5 Ni1 N1 88.37(14) . 3_765 ? N5 Ni1 N1 99.76(14) 3_765 3_765 ? N1 Ni1 N1 79.1(2) . 3_765 ? C2 C1 N1 109.5(4) . . ? C1 C2 N2 106.5(4) . . ? N1 C3 N2 112.5(4) . . ? N1 C3 C3 117.7(3) . 3_765 ? N2 C3 C3 129.7(3) . 3_765 ? C5 C4 N3 109.2(4) . . ? C4 C5 N4 107.0(4) . . ? N3 C6 N4 111.7(4) . . ? N3 C6 C7 117.9(4) . . ? N4 C6 C7 130.4(4) . . ? N5 C7 N6 112.1(4) . . ? N5 C7 C6 117.2(4) . . ? N6 C7 C6 130.6(4) . . ? C9 C8 N6 107.4(4) . . ? C8 C9 N5 108.9(4) . . ? C3 N1 C1 105.1(4) . . ? C3 N1 Ni1 112.5(3) . . ? C1 N1 Ni1 140.6(3) . . ? C3 N2 C2 106.4(4) . . ? C6 N3 C4 105.5(3) . . ? C6 N3 Ni1 112.7(3) . . ? C4 N3 Ni1 141.5(3) . . ? C6 N4 C5 106.6(4) . . ? C7 N5 C9 104.9(4) . . ? C7 N5 Ni1 113.0(3) . . ? C9 N5 Ni1 142.0(3) . . ? C7 N6 C8 106.7(4) . . ? O1 S1 O1 110.1(3) 3_765 . ? O1 S1 O2 109.19(19) 3_765 3_765 ? O1 S1 O2 109.6(2) . 3_765 ? O1 S1 O2 109.6(2) 3_765 . ? O1 S1 O2 109.19(19) . . ? O2 S1 O2 109.1(3) 3_765 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 60.90 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.169 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.065 data_L-4 _database_code_depnum_ccdc_archive 'CCDC 886487' #TrackingRef 'L-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 Mn N12 O4 S' _chemical_formula_weight 553.44 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M I4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' _cell_length_a 12.8656(6) _cell_length_b 12.8656(6) _cell_length_c 14.5185(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2403.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1132 _exptl_absorpt_coefficient_mu 0.688 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8746 _exptl_absorpt_correction_T_max 0.9344 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4678 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.95 _reflns_number_total 1547 _reflns_number_gt 1415 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+1.0126P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(3) _refine_ls_number_reflns 1547 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0880 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.049 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3105(3) 0.8109(3) 0.2094(3) 0.0603(12) Uani 1 1 d . . . H1 H 0.2626 0.8408 0.1672 0.072 Uiso 1 1 calc R . . C2 C 0.3011(3) 0.7151(4) 0.2478(3) 0.0536(10) Uani 1 1 d . . . H2 H 0.2472 0.6661 0.2371 0.064 Uiso 1 1 calc R . . C3 C 0.4402(3) 0.7895(3) 0.2995(3) 0.0403(8) Uani 1 1 d . . . C4 C 0.5371(3) 0.8154(3) 0.3465(3) 0.0379(8) Uani 1 1 d . . . C5 C 0.6731(3) 0.8228(3) 0.4355(3) 0.0488(10) Uani 1 1 d . . . H5 H 0.7231 0.8069 0.4815 0.059 Uiso 1 1 calc R . . C6 C 0.6739(3) 0.9055(3) 0.3781(3) 0.0452(9) Uani 1 1 d . . . H6 H 0.7262 0.9577 0.3766 0.054 Uiso 1 1 calc R . . C7 C 0.3017(3) 1.0676(3) 0.0726(3) 0.0546(11) Uani 1 1 d . . . H7 H 0.2490 1.0873 0.1150 0.066 Uiso 1 1 calc R . . C8 C 0.2889(3) 1.0637(3) -0.0202(3) 0.0559(11) Uani 1 1 d . . . H8 H 0.2280 1.0799 -0.0543 0.067 Uiso 1 1 calc R . . C9 C 0.4478(3) 1.0186(3) 0.0171(3) 0.0443(9) Uani 1 1 d . . . Mn1 Mn 0.5000 1.0000 0.21981(5) 0.0444(2) Uani 1 2 d S . . N1 N 0.3998(2) 0.8581(3) 0.2406(2) 0.0500(8) Uani 1 1 d . . . N2 N 0.3838(2) 0.7034(3) 0.3047(2) 0.0449(8) Uani 1 1 d . . . H2A H 0.3901 0.6625 0.3328 0.054 Uiso 1 1 d R . . N3 N 0.5872(2) 0.9026(2) 0.3217(2) 0.0430(7) Uani 1 1 d . . . H3 H 0.4007 1.0439 -0.1026 0.052 Uiso 1 1 d R . . N4 N 0.5858(2) 0.7665(2) 0.4144(2) 0.0408(7) Uani 1 1 d . . . H4 H 0.5644 0.7282 0.4388 0.049 Uiso 1 1 d R . . N5 N 0.4001(3) 1.0394(3) 0.0968(3) 0.0512(8) Uani 1 1 d . . . N6 N 0.3829(2) 1.0313(2) -0.0541(2) 0.0495(8) Uani 1 1 d . . . O1 O 0.5229(2) 0.5902(2) 0.5080(2) 0.0582(8) Uani 1 1 d . . . O2 O 0.5885(3) 0.4797(3) 0.3908(3) 0.0950(15) Uani 1 1 d . . . S1 S 0.5000 0.5000 0.44923(10) 0.0506(4) Uani 1 2 d S . . 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 C1 0.059(2) 0.066(3) 0.056(3) -0.015(2) -0.025(2) 0.010(2) C2 0.050(2) 0.066(3) 0.045(2) -0.015(2) -0.0108(19) -0.006(2) C3 0.0416(19) 0.047(2) 0.033(2) -0.0085(16) -0.0006(16) 0.0078(16) C4 0.0386(18) 0.0412(19) 0.0340(19) -0.0061(16) 0.0001(15) 0.0023(15) C5 0.051(2) 0.047(2) 0.049(3) 0.0016(18) -0.0110(18) -0.0051(17) C6 0.047(2) 0.041(2) 0.047(2) 0.0001(17) -0.0043(18) -0.0019(18) C7 0.047(2) 0.060(3) 0.056(3) 0.005(2) 0.006(2) 0.017(2) C8 0.046(2) 0.063(2) 0.059(3) 0.007(2) -0.007(2) 0.0104(18) C9 0.048(2) 0.048(2) 0.037(2) 0.0023(17) 0.0003(17) 0.0094(17) Mn1 0.0541(5) 0.0431(4) 0.0358(5) 0.000 0.000 0.0121(4) N1 0.0525(19) 0.0554(18) 0.042(2) -0.0066(15) -0.0112(15) 0.0068(15) N2 0.0450(17) 0.054(2) 0.0359(17) -0.0053(14) -0.0026(14) -0.0053(15) N3 0.0469(18) 0.0413(17) 0.0410(18) -0.0013(14) -0.0034(14) 0.0023(14) N4 0.0453(17) 0.0417(17) 0.0354(17) 0.0002(14) -0.0011(14) -0.0044(13) N5 0.0495(19) 0.061(2) 0.0434(19) 0.0039(16) 0.0044(16) 0.0182(16) N6 0.0512(19) 0.0543(18) 0.043(2) 0.0077(15) -0.0010(16) 0.0085(14) O1 0.091(2) 0.0432(15) 0.0406(17) 0.0036(13) 0.0023(16) -0.0115(14) O2 0.086(2) 0.104(3) 0.095(3) -0.054(2) 0.042(2) -0.050(2) S1 0.0596(8) 0.0546(8) 0.0375(10) 0.000 0.000 -0.0207(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 C1 C2 1.358(7) . ? C1 N1 1.377(5) . ? C2 N2 1.355(5) . ? C3 N2 1.326(5) . ? C3 N1 1.335(5) . ? C3 C4 1.461(5) . ? C4 N4 1.326(5) . ? C4 N3 1.343(5) . ? C5 C6 1.352(5) . ? C5 N4 1.371(5) . ? C6 N3 1.384(5) . ? C7 C8 1.358(7) . ? C7 N5 1.363(6) . ? C8 N6 1.370(5) . ? C9 N5 1.338(5) . ? C9 N6 1.339(5) . ? C9 C9 1.426(8) 6_564 ? Mn1 N3 2.240(3) 6_564 ? Mn1 N3 2.240(3) . ? Mn1 N1 2.254(3) 6_564 ? Mn1 N1 2.254(3) . ? Mn1 N5 2.258(4) . ? Mn1 N5 2.258(4) 6_564 ? O1 S1 1.471(3) . ? O2 S1 1.443(4) . ? S1 O2 1.443(4) 6_554 ? S1 O1 1.471(3) 6_554 ? 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 C2 C1 N1 109.8(4) . . ? N2 C2 C1 106.3(4) . . ? N2 C3 N1 112.1(3) . . ? N2 C3 C4 129.1(3) . . ? N1 C3 C4 118.7(3) . . ? N4 C4 N3 111.7(3) . . ? N4 C4 C3 129.9(3) . . ? N3 C4 C3 118.3(3) . . ? C6 C5 N4 106.6(4) . . ? C5 C6 N3 109.7(3) . . ? C8 C7 N5 111.0(4) . . ? C7 C8 N6 105.1(4) . . ? N5 C9 N6 111.0(3) . . ? N5 C9 C9 120.0(2) . 6_564 ? N6 C9 C9 128.9(2) . 6_564 ? N3 Mn1 N3 97.35(17) 6_564 . ? N3 Mn1 N1 75.23(12) 6_564 6_564 ? N3 Mn1 N1 94.49(12) . 6_564 ? N3 Mn1 N1 94.49(12) 6_564 . ? N3 Mn1 N1 75.23(12) . . ? N1 Mn1 N1 164.63(18) 6_564 . ? N3 Mn1 N5 96.38(12) 6_564 . ? N3 Mn1 N5 158.92(12) . . ? N1 Mn1 N5 104.44(13) 6_564 . ? N1 Mn1 N5 87.83(12) . . ? N3 Mn1 N5 158.92(12) 6_564 6_564 ? N3 Mn1 N5 96.38(12) . 6_564 ? N1 Mn1 N5 87.83(12) 6_564 6_564 ? N1 Mn1 N5 104.44(13) . 6_564 ? N5 Mn1 N5 75.50(17) . 6_564 ? C3 N1 C1 104.1(3) . . ? C3 N1 Mn1 113.5(2) . . ? C1 N1 Mn1 142.2(3) . . ? C3 N2 C2 107.6(4) . . ? C4 N3 C6 104.5(3) . . ? C4 N3 Mn1 113.9(2) . . ? C6 N3 Mn1 141.2(3) . . ? C4 N4 C5 107.6(3) . . ? C9 N5 C7 104.8(4) . . ? C9 N5 Mn1 112.2(2) . . ? C7 N5 Mn1 142.5(3) . . ? C9 N6 C8 108.1(4) . . ? O2 S1 O2 108.1(4) . 6_554 ? O2 S1 O1 108.99(17) . . ? O2 S1 O1 110.8(2) 6_554 . ? O2 S1 O1 110.8(2) . 6_554 ? O2 S1 O1 108.99(17) 6_554 6_554 ? O1 S1 O1 109.1(2) . 6_554 ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.95 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.209 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.049 data_L-5 _database_code_depnum_ccdc_archive 'CCDC 886488' #TrackingRef 'L-5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 Fe N12 O4 S' _chemical_formula_weight 554.35 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M I4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' _cell_length_a 12.8616(4) _cell_length_b 12.8616(4) _cell_length_c 14.3830(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2379.25(14) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.774 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8300 _exptl_absorpt_correction_T_max 0.8605 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9367 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.39 _reflns_number_total 2406 _reflns_number_gt 2014 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0444P)^2^+0.8456P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.020(19) _refine_ls_number_reflns 2406 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0858 _refine_ls_wR_factor_gt 0.0764 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 1.0000 0.5000 0.23190(4) 0.04473(16) Uani 1 2 d S . . C1 C 0.9109(2) 0.6717(2) 0.0728(2) 0.0540(7) Uani 1 1 d . . . H1 H 0.9634 0.7214 0.0732 0.065 Uiso 1 1 calc R . . C2 C 0.8273(2) 0.6726(2) 0.0162(2) 0.0555(7) Uani 1 1 d . . . H2A H 0.8116 0.7224 -0.0285 0.067 Uiso 1 1 calc R . . C3 C 0.81960(18) 0.5362(2) 0.1060(2) 0.0410(5) Uani 1 1 d . . . C4 C 0.7929(2) 0.4410(2) 0.1540(2) 0.0422(6) Uani 1 1 d . . . C5 C 0.7191(2) 0.3011(2) 0.2089(2) 0.0593(8) Uani 1 1 d . . . H5 H 0.6716 0.2481 0.2204 0.071 Uiso 1 1 calc R . . C6 C 0.8148(2) 0.3120(2) 0.2477(3) 0.0622(8) Uani 1 1 d . . . H6 H 0.8443 0.2666 0.2906 0.075 Uiso 1 1 calc R . . C7 C 0.98053(19) 0.5532(2) 0.4324(2) 0.0435(6) Uani 1 1 d . . . C8 C 0.9350(3) 0.7112(2) 0.4684(3) 0.0618(8) Uani 1 1 d . . . H8 H 0.9194 0.7714 0.5013 0.074 Uiso 1 1 calc R . . C9 C 0.9301(2) 0.6981(2) 0.3756(2) 0.0580(8) Uani 1 1 d . . . H9 H 0.9107 0.7493 0.3334 0.070 Uiso 1 1 calc R . . N1 N 0.90670(16) 0.58593(17) 0.12984(17) 0.0449(5) Uani 1 1 d . . . N2 N 0.76942(17) 0.58539(17) 0.03726(18) 0.0472(6) Uani 1 1 d . . . H2 H 0.7123 0.5663 0.0113 0.057 Uiso 1 1 calc R . . N3 N 0.86163(17) 0.40106(18) 0.21352(18) 0.0496(6) Uani 1 1 d . . . N4 N 0.70607(18) 0.38304(18) 0.14971(18) 0.0483(5) Uani 1 1 d . . . H4 H 0.6523 0.3953 0.1159 0.058 Uiso 1 1 calc R . . N5 N 0.95803(18) 0.59770(17) 0.35172(19) 0.0493(5) Uani 1 1 d . . . N6 N 0.96768(18) 0.61790(17) 0.50463(18) 0.0510(6) Uani 1 1 d . . . H6A H 0.9779 0.6038 0.5623 0.061 Uiso 1 1 calc R . . O1 O 0.40977(15) 0.47478(18) -0.05477(16) 0.0622(6) Uani 1 1 d . . . O2 O 0.5226(2) 0.4114(2) 0.0630(2) 0.0923(10) Uani 1 1 d . . . S1 S 0.5000 0.5000 0.00408(7) 0.0510(3) Uani 1 2 d S . . 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 Fe1 0.0426(3) 0.0513(3) 0.0403(4) 0.000 0.000 0.0059(2) C1 0.0494(16) 0.0521(16) 0.060(2) 0.0095(14) 0.0000(14) -0.0094(12) C2 0.0553(16) 0.0563(16) 0.055(2) 0.0182(14) -0.0043(13) -0.0062(12) C3 0.0404(12) 0.0460(13) 0.0367(14) 0.0002(11) 0.0033(11) 0.0016(9) C4 0.0426(13) 0.0450(13) 0.0391(16) 0.0007(11) 0.0076(11) 0.0011(10) C5 0.0657(19) 0.0561(17) 0.056(2) 0.0123(15) 0.0118(15) -0.0096(14) C6 0.0702(19) 0.0611(17) 0.055(2) 0.0202(16) 0.0045(17) 0.0001(14) C7 0.0477(14) 0.0415(13) 0.0415(16) -0.0013(12) 0.0026(11) 0.0048(10) C8 0.0730(19) 0.0432(15) 0.069(3) -0.0046(15) 0.0068(17) 0.0096(13) C9 0.0677(19) 0.0424(15) 0.064(2) 0.0083(14) 0.0065(16) 0.0170(13) N1 0.0429(11) 0.0474(12) 0.0445(14) 0.0067(10) -0.0021(10) 0.0000(9) N2 0.0419(12) 0.0544(13) 0.0454(15) 0.0073(11) -0.0042(11) -0.0042(9) N3 0.0508(12) 0.0538(13) 0.0442(15) 0.0100(10) 0.0016(10) 0.0023(10) N4 0.0474(12) 0.0544(13) 0.0431(14) 0.0024(11) 0.0045(10) -0.0067(9) N5 0.0566(13) 0.0468(12) 0.0446(14) 0.0020(11) 0.0027(11) 0.0125(10) N6 0.0634(14) 0.0473(12) 0.0423(16) -0.0044(10) 0.0039(11) 0.0048(9) O1 0.0424(11) 0.0952(15) 0.0489(14) 0.0080(12) -0.0037(9) -0.0121(10) O2 0.0980(19) 0.0861(18) 0.093(2) 0.0364(16) -0.0436(17) -0.0342(14) S1 0.0489(5) 0.0582(6) 0.0459(8) 0.000 0.000 -0.0116(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 Fe1 N1 2.195(2) 6_654 ? Fe1 N1 2.195(2) . ? Fe1 N5 2.200(3) . ? Fe1 N5 2.200(3) 6_654 ? Fe1 N3 2.204(2) . ? Fe1 N3 2.204(2) 6_654 ? C1 C2 1.350(4) . ? C1 N1 1.375(4) . ? C2 N2 1.379(3) . ? C3 N2 1.340(4) . ? C3 N1 1.335(3) . ? C3 C4 1.446(4) . ? C4 N3 1.334(4) . ? C4 N4 1.344(4) . ? C5 C6 1.360(5) . ? C5 N4 1.365(4) . ? C6 N3 1.385(4) . ? C7 N5 1.326(4) . ? C7 N6 1.341(4) . ? C7 C7 1.458(5) 6_654 ? C8 C9 1.347(5) . ? C8 N6 1.374(4) . ? C9 N5 1.383(4) . ? O1 S1 1.473(2) . ? O2 S1 1.449(3) . ? S1 O2 1.449(3) 6_554 ? S1 O1 1.473(2) 6_554 ? 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 Fe1 N1 96.04(13) 6_654 . ? N1 Fe1 N5 161.04(8) 6_654 . ? N1 Fe1 N5 95.86(9) . . ? N1 Fe1 N5 95.86(9) 6_654 6_654 ? N1 Fe1 N5 161.04(8) . 6_654 ? N5 Fe1 N5 76.87(12) . 6_654 ? N1 Fe1 N3 94.04(9) 6_654 . ? N1 Fe1 N3 76.65(8) . . ? N5 Fe1 N3 103.04(9) . . ? N5 Fe1 N3 87.84(9) 6_654 . ? N1 Fe1 N3 76.65(8) 6_654 6_654 ? N1 Fe1 N3 94.04(9) . 6_654 ? N5 Fe1 N3 87.84(9) . 6_654 ? N5 Fe1 N3 103.04(9) 6_654 6_654 ? N3 Fe1 N3 166.22(13) . 6_654 ? C2 C1 N1 109.6(2) . . ? C1 C2 N2 106.9(3) . . ? N2 C3 N1 111.5(2) . . ? N2 C3 C4 129.6(2) . . ? N1 C3 C4 118.9(2) . . ? N3 C4 N4 111.5(2) . . ? N3 C4 C3 118.3(2) . . ? N4 C4 C3 130.2(3) . . ? C6 C5 N4 106.7(3) . . ? C5 C6 N3 109.4(3) . . ? N5 C7 N6 112.6(2) . . ? N5 C7 C7 118.69(15) . 6_654 ? N6 C7 C7 128.67(16) . 6_654 ? C9 C8 N6 106.3(3) . . ? C8 C9 N5 110.5(3) . . ? C3 N1 C1 105.4(2) . . ? C3 N1 Fe1 112.89(17) . . ? C1 N1 Fe1 141.35(18) . . ? C3 N2 C2 106.6(2) . . ? C4 N3 C6 105.0(2) . . ? C4 N3 Fe1 112.95(17) . . ? C6 N3 Fe1 141.8(2) . . ? C4 N4 C5 107.3(3) . . ? C7 N5 C9 104.0(3) . . ? C7 N5 Fe1 112.69(16) . . ? C9 N5 Fe1 142.3(2) . . ? C7 N6 C8 106.6(3) . . ? O2 S1 O2 108.4(3) . 6_554 ? O2 S1 O1 108.72(13) . . ? O2 S1 O1 110.57(15) 6_554 . ? O2 S1 O1 110.57(15) . 6_554 ? O2 S1 O1 108.72(13) 6_554 6_554 ? O1 S1 O1 109.83(19) . 6_554 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.86 1.91 2.768(3) 175.9 6_554 N4 H4 O2 0.86 1.85 2.694(3) 168.8 . N6 H6A O1 0.86 1.92 2.766(3) 167.7 4_565 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.39 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.167 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.056 data_L-6 _database_code_depnum_ccdc_archive 'CCDC 886489' #TrackingRef 'L-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N12 O4 S Zn' _chemical_formula_weight 563.87 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M I4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' _cell_length_a 12.8115(14) _cell_length_b 12.8115(14) _cell_length_c 14.325(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2351.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 1.187 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6482 _exptl_absorpt_correction_T_max 0.8906 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4533 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.96 _reflns_number_total 1880 _reflns_number_gt 1565 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment contr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.004(15) _refine_ls_number_reflns 1880 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0866 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.5000 1.0000 0.23539(4) 0.0557(2) Uani 1 2 d S . . S1 S 0.5000 1.0000 0.75796(9) 0.0588(4) Uani 1 2 d S . . N3 N 0.4073(2) 1.0855(2) 0.1348(2) 0.0532(7) Uani 1 1 d . . . N6 N 0.5326(2) 0.8815(2) 0.5073(2) 0.0597(8) Uani 1 1 d . . . H6B H 0.5105 0.8915 0.5662 0.089 Uiso 1 1 d R . . N2 N 0.2055(3) 0.8822(2) 0.1544(2) 0.0576(8) Uani 1 1 d . . . H2B H 0.1483 0.8815 0.1095 0.086 Uiso 1 1 d R . . C7 C 0.5696(3) 0.8021(3) 0.3770(3) 0.0677(11) Uani 1 1 d . . . H7A H 0.5893 0.7503 0.3340 0.081 Uiso 1 1 calc R . . N4 N 0.2700(2) 1.0848(2) 0.0419(2) 0.0554(8) Uani 1 1 d . . . H4B H 0.2087 1.0650 0.0069 0.083 Uiso 1 1 d R . . C1 C 0.3156(3) 0.8100(3) 0.2513(3) 0.0699(11) Uani 1 1 d . . . H1A H 0.3459 0.7637 0.2943 0.084 Uiso 1 1 calc R . . N1 N 0.3615(2) 0.8997(2) 0.2175(2) 0.0586(8) Uani 1 1 d . . . O2 O 0.5239(2) 0.9092(2) 0.6986(2) 0.0697(8) Uani 1 1 d . . . C4 C 0.3200(3) 1.0354(3) 0.1113(3) 0.0478(8) Uani 1 1 d . . . C6 C 0.3274(3) 1.1725(3) 0.0208(3) 0.0643(10) Uani 1 1 d . . . H6A H 0.3115 1.2232 -0.0245 0.077 Uiso 1 1 calc R . . C3 C 0.2932(3) 0.9393(3) 0.1589(3) 0.0508(8) Uani 1 1 d . . . C8 C 0.5642(3) 0.7884(3) 0.4712(3) 0.0708(11) Uani 1 1 d . . . H8A H 0.5793 0.7271 0.5045 0.085 Uiso 1 1 calc R . . N5 N 0.5419(2) 0.9022(2) 0.3542(2) 0.0596(8) Uani 1 1 d . . . C5 C 0.4115(3) 1.1713(3) 0.0787(3) 0.0600(9) Uani 1 1 d . . . H5A H 0.4646 1.2219 0.0798 0.072 Uiso 1 1 calc R . . C9 C 0.5193(3) 0.9472(3) 0.4356(3) 0.0541(9) Uani 1 1 d . . . C2 C 0.2201(3) 0.7994(3) 0.2127(3) 0.0685(11) Uani 1 1 d . . . H2A H 0.1724 0.7450 0.2239 0.082 Uiso 1 1 calc R . . O1 O 0.5891(3) 1.0219(3) 0.8176(3) 0.1004(12) 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 Zn1 0.0547(4) 0.0639(4) 0.0485(4) 0.000 0.000 0.0074(3) S1 0.0669(8) 0.0577(8) 0.0518(12) 0.000 0.000 0.0125(6) N3 0.0559(18) 0.0575(18) 0.0461(17) 0.0015(14) 0.0014(14) 0.0012(14) N6 0.0673(19) 0.0603(18) 0.051(2) 0.0062(15) -0.0003(15) 0.0038(14) N2 0.0619(19) 0.0648(19) 0.0461(18) 0.0013(15) 0.0084(14) -0.0093(15) C7 0.073(3) 0.056(2) 0.074(3) -0.011(2) -0.001(2) 0.010(2) N4 0.0513(17) 0.0638(19) 0.0510(18) 0.0029(15) -0.0005(15) -0.0033(15) C1 0.082(3) 0.070(2) 0.057(3) 0.018(2) 0.008(2) 0.003(2) N1 0.0615(17) 0.0655(19) 0.0490(19) 0.0091(15) 0.0087(15) 0.0013(15) O2 0.101(2) 0.0492(15) 0.0588(18) 0.0004(13) -0.0102(16) 0.0082(14) C4 0.0454(18) 0.058(2) 0.0397(18) -0.0022(15) 0.0029(15) 0.0033(16) C6 0.063(2) 0.063(2) 0.066(3) 0.0140(19) 0.000(2) -0.0024(19) C3 0.054(2) 0.055(2) 0.043(2) -0.0012(16) 0.0097(16) 0.0020(17) C8 0.078(3) 0.058(2) 0.077(3) 0.008(2) -0.002(2) 0.007(2) N5 0.0648(19) 0.0589(18) 0.0550(19) -0.0034(16) -0.0004(15) 0.0108(15) C5 0.056(2) 0.061(2) 0.063(2) 0.0080(19) -0.0012(19) -0.0060(19) C9 0.060(2) 0.0507(19) 0.051(2) 0.0002(18) -0.0029(16) 0.0062(17) C2 0.074(3) 0.069(3) 0.063(3) 0.013(2) 0.016(2) -0.007(2) O1 0.091(2) 0.105(3) 0.105(3) -0.036(2) -0.036(2) 0.0378(19) _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 Zn1 N3 2.165(3) 6_564 ? Zn1 N3 2.165(3) . ? Zn1 N5 2.181(3) . ? Zn1 N5 2.181(3) 6_564 ? Zn1 N1 2.205(3) 6_564 ? Zn1 N1 2.205(3) . ? S1 O1 1.453(3) . ? S1 O1 1.453(3) 6_564 ? S1 O2 1.472(3) . ? S1 O2 1.472(3) 6_564 ? N3 C4 1.333(5) . ? N3 C5 1.363(5) . ? N6 C9 1.338(5) . ? N6 C8 1.362(5) . ? N2 C3 1.342(5) . ? N2 C2 1.363(5) . ? C7 C8 1.362(6) . ? C7 N5 1.370(5) . ? N4 C4 1.341(5) . ? N4 C6 1.375(5) . ? C1 C2 1.349(6) . ? C1 N1 1.380(5) . ? N1 C3 1.315(5) . ? C4 C3 1.449(5) . ? C6 C5 1.361(5) . ? N5 C9 1.333(5) . ? C9 C9 1.441(7) 6_564 ? 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 N3 Zn1 N3 96.55(17) 6_564 . ? N3 Zn1 N5 95.38(11) 6_564 . ? N3 Zn1 N5 160.96(11) . . ? N3 Zn1 N5 160.96(11) 6_564 6_564 ? N3 Zn1 N5 95.38(11) . 6_564 ? N5 Zn1 N5 77.39(17) . 6_564 ? N3 Zn1 N1 77.03(11) 6_564 6_564 ? N3 Zn1 N1 93.97(12) . 6_564 ? N5 Zn1 N1 103.15(12) . 6_564 ? N5 Zn1 N1 87.38(12) 6_564 6_564 ? N3 Zn1 N1 93.97(12) 6_564 . ? N3 Zn1 N1 77.03(11) . . ? N5 Zn1 N1 87.38(12) . . ? N5 Zn1 N1 103.15(12) 6_564 . ? N1 Zn1 N1 166.62(16) 6_564 . ? O1 S1 O1 108.0(3) . 6_564 ? O1 S1 O2 109.17(16) . . ? O1 S1 O2 110.49(19) 6_564 . ? O1 S1 O2 110.49(19) . 6_564 ? O1 S1 O2 109.17(16) 6_564 6_564 ? O2 S1 O2 109.5(2) . 6_564 ? C4 N3 C5 105.8(3) . . ? C4 N3 Zn1 112.7(2) . . ? C5 N3 Zn1 141.1(3) . . ? C9 N6 C8 107.3(3) . . ? C3 N2 C2 106.3(3) . . ? C8 C7 N5 110.1(4) . . ? C4 N4 C6 107.1(3) . . ? C2 C1 N1 109.1(4) . . ? C3 N1 C1 105.1(3) . . ? C3 N1 Zn1 112.7(2) . . ? C1 N1 Zn1 142.0(3) . . ? N3 C4 N4 111.1(3) . . ? N3 C4 C3 119.3(3) . . ? N4 C4 C3 129.6(3) . . ? C5 C6 N4 106.3(4) . . ? N1 C3 N2 112.2(3) . . ? N1 C3 C4 118.0(3) . . ? N2 C3 C4 129.7(3) . . ? N6 C8 C7 106.2(4) . . ? C9 N5 C7 104.6(4) . . ? C9 N5 Zn1 112.4(2) . . ? C7 N5 Zn1 142.0(3) . . ? C6 C5 N3 109.7(4) . . ? N5 C9 N6 111.8(3) . . ? N5 C9 C9 118.7(2) . 6_564 ? N6 C9 C9 129.4(2) . 6_564 ? C1 C2 N2 107.3(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.96 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.210 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.054 data_rac-2 _database_code_depnum_ccdc_archive 'CCDC 886490' #TrackingRef 'rac-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H18 Co N12 O4 S' _chemical_formula_sum 'C18 H18 Co N12 O4 S' _chemical_formula_weight 557.43 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.561(3) _cell_length_b 20.722(4) _cell_length_c 23.556(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.26(3) _cell_angle_gamma 90.00 _cell_volume 6052(2) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelpied _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2280 _exptl_absorpt_coefficient_mu 0.678 _exptl_absorpt_correction_type 'multi-scan ' _exptl_absorpt_correction_T_min 0.8226 _exptl_absorpt_correction_T_max 0.8764 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 34413 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 28.11 _reflns_number_total 13476 _reflns_number_gt 9990 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1137P)^2^+2.3517P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13476 _refine_ls_number_parameters 649 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1893 _refine_ls_wR_factor_gt 0.1782 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 1.18247(3) 0.20431(2) -0.231846(17) 0.02416(12) Uani 1 1 d . . . Co2 Co 1.59370(3) 0.26815(2) 0.093506(17) 0.02509(13) Uani 1 1 d . . . S1 S 1.06044(6) 0.28048(5) -0.02859(3) 0.0349(2) Uani 1 1 d . . . S2 S 1.71539(6) 0.18444(4) -0.11150(3) 0.02807(18) Uani 1 1 d . . . O1 O 1.1477(2) 0.26111(15) -0.05833(12) 0.0497(7) Uani 1 1 d . . . O2 O 0.96104(19) 0.29289(13) -0.06998(10) 0.0386(6) Uani 1 1 d . . . O3 O 1.0406(2) 0.22556(17) 0.01047(13) 0.0598(8) Uani 1 1 d . . . O4 O 1.0912(2) 0.33712(17) 0.00685(13) 0.0588(8) Uani 1 1 d . . . O5 O 1.62415(19) 0.19276(13) -0.08047(10) 0.0380(6) Uani 1 1 d . . . O6 O 1.81444(18) 0.16925(12) -0.07154(9) 0.0337(5) Uani 1 1 d . . . O7 O 1.73034(18) 0.24379(12) -0.14440(10) 0.0335(5) Uani 1 1 d . . . O8 O 1.69058(19) 0.13064(12) -0.15355(10) 0.0360(5) Uani 1 1 d . . . N1 N 1.2817(2) 0.25251(12) -0.17633(11) 0.0264(5) Uani 1 1 d . . . N2 N 1.4425(2) 0.26029(13) -0.12356(11) 0.0286(6) Uani 1 1 d . . . H2A H 1.5076 0.2513 -0.1082 0.034 Uiso 1 1 calc R . . N3 N 1.3048(2) 0.14794(12) -0.22998(11) 0.0251(5) Uani 1 1 d . . . N4 N 1.4719(2) 0.12371(13) -0.19318(12) 0.0308(6) Uani 1 1 d . . . H4A H 1.5346 0.1250 -0.1722 0.037 Uiso 1 1 calc R . . N5 N 1.1289(2) 0.15719(13) -0.17170(11) 0.0271(5) Uani 1 1 d . . . N6 N 1.0044(2) 0.14671(15) -0.11643(12) 0.0356(6) Uani 1 1 d . . . H6A H 0.9469 0.1528 -0.1017 0.043 Uiso 1 1 calc R . . N7 N 1.0591(2) 0.25819(12) -0.22759(11) 0.0262(5) Uani 1 1 d . . . N8 N 0.9071(2) 0.27270(13) -0.19429(12) 0.0300(6) Uani 1 1 d . . . H8A H 0.8558 0.2674 -0.1746 0.036 Uiso 1 1 calc R . . N9 N 1.1006(2) 0.15374(13) -0.29224(11) 0.0271(5) Uani 1 1 d . . . N10 N 1.0491(2) 0.13690(14) -0.38471(12) 0.0325(6) Uani 1 1 d . . . H10A H 1.0398 0.1424 -0.4214 0.039 Uiso 1 1 calc R . . N11 N 1.2140(2) 0.25510(13) -0.29563(11) 0.0282(6) Uani 1 1 d . . . N12 N 1.1692(2) 0.28055(14) -0.38702(12) 0.0334(6) Uani 1 1 d . . . H12A H 1.1410 0.2785 -0.4227 0.040 Uiso 1 1 calc R . . N13 N 1.7141(2) 0.21150(13) 0.09212(11) 0.0271(5) Uani 1 1 d . . . N14 N 1.8622(2) 0.18862(14) 0.05778(12) 0.0337(6) Uani 1 1 d . . . H14B H 1.9125 0.1902 0.0370 0.040 Uiso 1 1 calc R . . N15 N 1.6468(2) 0.30801(13) 0.02979(11) 0.0269(5) Uani 1 1 d . . . N16 N 1.7717(2) 0.31324(14) -0.02521(11) 0.0304(6) Uani 1 1 d . . . H16A H 1.8289 0.3051 -0.0397 0.036 Uiso 1 1 calc R . . N17 N 1.5631(2) 0.22652(13) 0.16249(11) 0.0271(6) Uani 1 1 d . . . N18 N 1.6016(2) 0.21890(14) 0.25671(12) 0.0334(6) Uani 1 1 d . . . H18B H 1.6273 0.2276 0.2919 0.040 Uiso 1 1 calc R . . N19 N 1.6771(2) 0.32529(13) 0.14762(11) 0.0282(6) Uani 1 1 d . . . N20 N 1.7236(2) 0.35784(14) 0.23668(12) 0.0327(6) Uani 1 1 d . . . H20A H 1.7301 0.3591 0.2736 0.039 Uiso 1 1 calc R . . N21 N 1.4721(2) 0.32573(13) 0.08656(11) 0.0289(6) Uani 1 1 d . . . N22 N 1.3074(2) 0.35027(14) 0.04620(12) 0.0330(6) Uani 1 1 d . . . H22A H 1.2444 0.3475 0.0257 0.040 Uiso 1 1 calc R . . N23 N 1.4928(2) 0.21501(13) 0.04363(11) 0.0269(5) Uani 1 1 d . . . N24 N 1.3320(2) 0.20370(14) -0.00863(12) 0.0320(6) Uani 1 1 d . . . H24A H 1.2669 0.2118 -0.0246 0.038 Uiso 1 1 calc R . . C1 C 1.3782(2) 0.22398(15) -0.16175(13) 0.0264(6) Uani 1 1 d . . . C2 C 1.3855(3) 0.31461(16) -0.11344(14) 0.0304(7) Uani 1 1 d . . . H2B H 1.4104 0.3486 -0.0891 0.037 Uiso 1 1 calc R . . C3 C 1.2850(3) 0.30922(15) -0.14610(13) 0.0284(7) Uani 1 1 d . . . H3A H 1.2289 0.3388 -0.1475 0.034 Uiso 1 1 calc R . . C4 C 1.3911(2) 0.16560(15) -0.19207(13) 0.0271(6) Uani 1 1 d . . . C5 C 1.3323(3) 0.09389(16) -0.25659(14) 0.0314(7) Uani 1 1 d . . . H5A H 1.2879 0.0714 -0.2853 0.038 Uiso 1 1 calc R . . C6 C 1.4354(3) 0.07806(16) -0.23423(15) 0.0337(7) Uani 1 1 d . . . H6B H 1.4742 0.0430 -0.2447 0.040 Uiso 1 1 calc R . . C7 C 1.0357(3) 0.18087(16) -0.15916(14) 0.0284(7) Uani 1 1 d . . . C8 C 1.1579(3) 0.10692(16) -0.13509(14) 0.0331(7) Uani 1 1 d . . . H8B H 1.2193 0.0817 -0.1340 0.040 Uiso 1 1 calc R . . C9 C 1.0817(3) 0.09990(18) -0.10045(16) 0.0384(8) Uani 1 1 d . . . H9A H 1.0818 0.0694 -0.0715 0.046 Uiso 1 1 calc R . . C10 C 0.9967(2) 0.23643(15) -0.19145(13) 0.0265(6) Uani 1 1 d . . . C11 C 1.0079(3) 0.31066(16) -0.25502(14) 0.0314(7) Uani 1 1 d . . . H11A H 1.0333 0.3357 -0.2827 0.038 Uiso 1 1 calc R . . C12 C 0.9133(3) 0.31973(16) -0.23471(14) 0.0334(7) Uani 1 1 d . . . H12B H 0.8625 0.3518 -0.2461 0.040 Uiso 1 1 calc R . . C13 C 1.1019(3) 0.17702(16) -0.34460(14) 0.0295(7) Uani 1 1 d . . . C14 C 1.0453(2) 0.09619(16) -0.29855(15) 0.0310(7) Uani 1 1 d . . . H14A H 1.0320 0.0690 -0.2691 0.037 Uiso 1 1 calc R . . C15 C 1.0134(3) 0.08634(17) -0.35643(16) 0.0376(8) Uani 1 1 d . . . H15A H 0.9743 0.0512 -0.3732 0.045 Uiso 1 1 calc R . . C16 C 1.1606(3) 0.23615(16) -0.34631(13) 0.0280(7) Uani 1 1 d . . . C17 C 1.2577(3) 0.31421(16) -0.30425(14) 0.0317(7) Uani 1 1 d . . . H17A H 1.2984 0.3394 -0.2761 0.038 Uiso 1 1 calc R . . C18 C 1.2316(3) 0.32979(18) -0.36068(15) 0.0376(8) Uani 1 1 d . . . H18A H 1.2521 0.3669 -0.3783 0.045 Uiso 1 1 calc R . . C19 C 1.7765(2) 0.22779(16) 0.05356(13) 0.0277(6) Uani 1 1 d . . . C20 C 1.7629(3) 0.15930(17) 0.12221(15) 0.0347(7) Uani 1 1 d . . . H20B H 1.7372 0.1373 0.1517 0.042 Uiso 1 1 calc R . . C21 C 1.8553(3) 0.14580(18) 0.10104(16) 0.0402(8) Uani 1 1 d . . . H21A H 1.9046 0.1134 0.1138 0.048 Uiso 1 1 calc R . . C22 C 1.7387(2) 0.28151(16) 0.01850(13) 0.0271(6) Uani 1 1 d . . . C23 C 1.6211(3) 0.35760(15) -0.00800(13) 0.0296(7) Uani 1 1 d . . . H23A H 1.5614 0.3845 -0.0098 0.036 Uiso 1 1 calc R . . C24 C 1.6984(3) 0.36087(16) -0.04273(14) 0.0314(7) Uani 1 1 d . . . H24B H 1.7006 0.3899 -0.0726 0.038 Uiso 1 1 calc R . . C25 C 1.6128(3) 0.25472(16) 0.21078(14) 0.0295(7) Uani 1 1 d . . . C26 C 1.5417(3) 0.16602(18) 0.23735(15) 0.0364(8) Uani 1 1 d . . . H26A H 1.5206 0.1330 0.2598 0.044 Uiso 1 1 calc R . . C27 C 1.5187(3) 0.17064(16) 0.17907(15) 0.0326(7) Uani 1 1 d . . . H27A H 1.4794 0.1409 0.1546 0.039 Uiso 1 1 calc R . . C28 C 1.6726(2) 0.31242(16) 0.20202(13) 0.0278(6) Uani 1 1 d . . . C29 C 1.7344(3) 0.38194(16) 0.14698(15) 0.0323(7) Uani 1 1 d . . . H29A H 1.7504 0.4028 0.1144 0.039 Uiso 1 1 calc R . . C30 C 1.7635(3) 0.40183(17) 0.20224(15) 0.0352(7) Uani 1 1 d . . . H30A H 1.8032 0.4386 0.2144 0.042 Uiso 1 1 calc R . . C31 C 1.3858(3) 0.30590(15) 0.05020(13) 0.0275(6) Uani 1 1 d . . . C32 C 1.4483(3) 0.38617(16) 0.10565(15) 0.0335(7) Uani 1 1 d . . . H32A H 1.4941 0.4121 0.1310 0.040 Uiso 1 1 calc R . . C33 C 1.3460(3) 0.40095(17) 0.08081(15) 0.0357(8) Uani 1 1 d . . . H33A H 1.3089 0.4387 0.0863 0.043 Uiso 1 1 calc R . . C34 C 1.3970(2) 0.24326(15) 0.02644(13) 0.0270(6) Uani 1 1 d . . . C35 C 1.4877(3) 0.15517(16) 0.01840(15) 0.0348(7) Uani 1 1 d . . . H35A H 1.5426 0.1246 0.0228 0.042 Uiso 1 1 calc R . . C36 C 1.3878(3) 0.14831(17) -0.01433(15) 0.0368(8) Uani 1 1 d . . . H36A H 1.3628 0.1125 -0.0363 0.044 Uiso 1 1 calc R . . 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 Co1 0.0213(2) 0.0265(2) 0.0240(2) -0.00296(16) 0.00155(16) -0.00069(16) Co2 0.0221(2) 0.0288(2) 0.0239(2) 0.00134(16) 0.00194(16) -0.00210(16) S1 0.0210(4) 0.0583(6) 0.0241(4) -0.0007(4) 0.0003(3) 0.0012(4) S2 0.0211(4) 0.0382(4) 0.0239(4) 0.0012(3) 0.0008(3) 0.0031(3) O1 0.0320(14) 0.074(2) 0.0421(15) -0.0041(13) 0.0018(11) 0.0114(13) O2 0.0246(12) 0.0584(16) 0.0304(12) -0.0010(11) -0.0029(10) 0.0051(11) O3 0.0363(15) 0.093(2) 0.0474(17) 0.0249(16) -0.0003(13) -0.0032(15) O4 0.0412(16) 0.079(2) 0.0524(17) -0.0159(16) -0.0035(13) 0.0019(15) O5 0.0258(12) 0.0552(15) 0.0339(13) 0.0016(11) 0.0073(10) 0.0050(11) O6 0.0260(12) 0.0463(14) 0.0276(11) 0.0034(10) 0.0009(9) 0.0076(10) O7 0.0275(12) 0.0413(13) 0.0301(12) 0.0024(10) 0.0000(9) 0.0033(10) O8 0.0343(13) 0.0423(14) 0.0300(12) -0.0028(10) 0.0013(10) -0.0016(10) N1 0.0262(13) 0.0248(13) 0.0276(13) -0.0020(10) 0.0028(11) 0.0004(10) N2 0.0249(13) 0.0334(14) 0.0265(13) -0.0040(11) 0.0008(11) -0.0010(11) N3 0.0219(13) 0.0269(13) 0.0263(13) -0.0043(10) 0.0031(10) -0.0027(10) N4 0.0257(14) 0.0294(14) 0.0359(15) -0.0064(11) 0.0010(11) 0.0021(11) N5 0.0236(13) 0.0312(13) 0.0267(13) -0.0014(10) 0.0044(10) 0.0031(10) N6 0.0288(15) 0.0440(17) 0.0349(15) 0.0103(13) 0.0079(12) 0.0062(12) N7 0.0230(13) 0.0291(13) 0.0254(13) -0.0029(10) 0.0000(10) 0.0018(10) N8 0.0236(13) 0.0361(15) 0.0304(14) 0.0001(11) 0.0045(11) 0.0059(11) N9 0.0214(13) 0.0310(14) 0.0281(13) -0.0023(11) 0.0020(10) -0.0021(10) N10 0.0312(15) 0.0376(15) 0.0264(14) -0.0034(11) -0.0030(11) -0.0024(12) N11 0.0271(14) 0.0329(14) 0.0244(13) -0.0058(11) 0.0038(11) -0.0042(11) N12 0.0354(16) 0.0384(16) 0.0254(14) 0.0008(11) 0.0024(12) -0.0022(12) N13 0.0240(13) 0.0309(14) 0.0255(13) 0.0024(10) 0.0016(10) -0.0005(10) N14 0.0247(14) 0.0430(16) 0.0320(15) 0.0033(12) -0.0001(11) 0.0090(12) N15 0.0224(13) 0.0325(14) 0.0253(13) 0.0018(11) 0.0024(10) -0.0004(11) N16 0.0248(14) 0.0391(15) 0.0280(14) 0.0054(11) 0.0065(11) 0.0017(11) N17 0.0229(13) 0.0313(14) 0.0266(13) -0.0008(11) 0.0028(10) -0.0075(11) N18 0.0312(15) 0.0429(16) 0.0261(14) 0.0044(12) 0.0044(11) -0.0039(12) N19 0.0262(14) 0.0312(14) 0.0266(13) 0.0035(11) 0.0023(11) -0.0012(11) N20 0.0313(15) 0.0376(15) 0.0279(14) -0.0015(11) 0.0009(11) -0.0043(12) N21 0.0260(14) 0.0296(14) 0.0311(14) 0.0001(11) 0.0045(11) -0.0021(11) N22 0.0222(13) 0.0356(15) 0.0406(16) -0.0003(12) 0.0034(12) -0.0002(11) N23 0.0238(13) 0.0305(14) 0.0257(13) 0.0000(10) 0.0017(10) -0.0013(10) N24 0.0255(14) 0.0359(15) 0.0323(15) -0.0031(11) -0.0022(11) -0.0031(11) C1 0.0243(15) 0.0294(15) 0.0254(15) -0.0023(12) 0.0034(12) -0.0010(12) C2 0.0298(17) 0.0303(16) 0.0303(16) -0.0068(13) 0.0023(13) -0.0023(13) C3 0.0280(16) 0.0269(15) 0.0288(16) -0.0042(12) 0.0004(13) 0.0039(12) C4 0.0209(15) 0.0324(16) 0.0270(15) -0.0008(12) 0.0010(12) -0.0007(12) C5 0.0302(17) 0.0291(16) 0.0343(17) -0.0077(13) 0.0040(13) -0.0040(13) C6 0.0311(17) 0.0279(16) 0.0416(19) -0.0097(14) 0.0040(14) 0.0032(13) C7 0.0243(15) 0.0323(17) 0.0289(16) -0.0014(13) 0.0050(12) 0.0034(12) C8 0.0304(17) 0.0328(17) 0.0359(18) 0.0014(14) 0.0043(14) 0.0033(13) C9 0.0374(19) 0.0396(19) 0.0380(19) 0.0128(15) 0.0058(15) 0.0087(15) C10 0.0218(15) 0.0326(16) 0.0234(15) -0.0010(12) -0.0017(12) 0.0010(12) C11 0.0341(18) 0.0294(16) 0.0290(16) 0.0051(13) -0.0005(13) 0.0013(13) C12 0.0326(18) 0.0319(17) 0.0336(17) 0.0037(13) -0.0009(14) 0.0084(14) C13 0.0261(16) 0.0333(17) 0.0283(16) -0.0035(13) 0.0016(13) -0.0002(13) C14 0.0226(15) 0.0296(16) 0.0392(18) -0.0009(13) 0.0001(13) -0.0041(12) C15 0.0320(18) 0.0328(17) 0.045(2) -0.0057(15) -0.0023(15) -0.0078(14) C16 0.0248(16) 0.0350(17) 0.0239(15) -0.0011(12) 0.0031(12) 0.0012(13) C17 0.0304(17) 0.0322(17) 0.0323(17) -0.0036(13) 0.0044(13) -0.0067(13) C18 0.0380(19) 0.0372(19) 0.0383(19) 0.0048(15) 0.0079(15) -0.0054(15) C19 0.0216(15) 0.0363(17) 0.0239(15) -0.0009(12) -0.0004(12) 0.0002(12) C20 0.0359(18) 0.0334(18) 0.0336(18) 0.0066(14) 0.0020(14) 0.0020(14) C21 0.0354(19) 0.044(2) 0.040(2) 0.0083(16) 0.0009(15) 0.0101(16) C22 0.0228(15) 0.0353(17) 0.0225(15) 0.0012(12) 0.0015(12) -0.0008(12) C23 0.0300(17) 0.0307(16) 0.0268(15) 0.0032(13) 0.0003(13) 0.0026(13) C24 0.0341(17) 0.0308(17) 0.0287(16) 0.0048(13) 0.0036(13) -0.0019(13) C25 0.0230(15) 0.0371(17) 0.0278(16) 0.0018(13) 0.0024(12) -0.0027(13) C26 0.0308(18) 0.0396(19) 0.0397(19) 0.0080(15) 0.0090(15) -0.0068(14) C27 0.0281(17) 0.0336(17) 0.0368(18) 0.0036(14) 0.0076(14) -0.0070(13) C28 0.0227(15) 0.0327(16) 0.0275(15) 0.0006(12) 0.0023(12) -0.0031(12) C29 0.0257(16) 0.0334(17) 0.0377(18) 0.0027(14) 0.0051(13) -0.0089(13) C30 0.0329(18) 0.0337(18) 0.0378(18) -0.0020(14) 0.0019(14) -0.0080(14) C31 0.0235(15) 0.0310(16) 0.0284(16) 0.0021(12) 0.0050(12) -0.0008(12) C32 0.0319(17) 0.0326(17) 0.0371(18) -0.0070(14) 0.0086(14) -0.0032(14) C33 0.0299(17) 0.0333(18) 0.045(2) -0.0044(15) 0.0105(15) 0.0016(14) C34 0.0223(15) 0.0328(16) 0.0252(15) 0.0011(12) 0.0016(12) -0.0020(12) C35 0.0351(18) 0.0270(16) 0.0399(19) -0.0019(14) -0.0011(15) 0.0010(14) C36 0.0391(19) 0.0312(17) 0.0375(19) -0.0051(14) -0.0018(15) -0.0020(14) _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 Co1 N3 1.925(3) . ? Co1 N9 1.926(3) . ? Co1 N7 1.926(3) . ? Co1 N11 1.927(3) . ? Co1 N5 1.929(3) . ? Co1 N1 1.933(3) . ? Co2 N13 1.919(3) . ? Co2 N19 1.922(3) . ? Co2 N15 1.924(3) . ? Co2 N21 1.925(3) . ? Co2 N23 1.929(3) . ? Co2 N17 1.932(3) . ? S1 O1 1.449(3) . ? S1 O4 1.456(3) . ? S1 O2 1.478(2) . ? S1 O3 1.509(3) . ? S2 O5 1.465(2) . ? S2 O6 1.468(2) . ? S2 O7 1.482(2) . ? S2 O8 1.491(2) . ? N1 C1 1.342(4) . ? N1 C3 1.371(4) . ? N2 C1 1.339(4) . ? N2 C2 1.375(4) . ? N2 H2A 0.8600 . ? N3 C4 1.340(4) . ? N3 C5 1.355(4) . ? N4 C4 1.339(4) . ? N4 C6 1.377(4) . ? N4 H4A 0.8600 . ? N5 C7 1.345(4) . ? N5 C8 1.364(4) . ? N6 C7 1.340(4) . ? N6 C9 1.381(4) . ? N6 H6A 0.8600 . ? N7 C10 1.325(4) . ? N7 C11 1.371(4) . ? N8 C10 1.347(4) . ? N8 C12 1.374(4) . ? N8 H8A 0.8600 . ? N9 C13 1.327(4) . ? N9 C14 1.376(4) . ? N10 C13 1.350(4) . ? N10 C15 1.356(4) . ? N10 H10A 0.8600 . ? N11 C16 1.331(4) . ? N11 C17 1.371(4) . ? N12 C16 1.346(4) . ? N12 C18 1.372(5) . ? N12 H12A 0.8600 . ? N13 C19 1.335(4) . ? N13 C20 1.381(4) . ? N14 C19 1.339(4) . ? N14 C21 1.364(5) . ? N14 H14B 0.8600 . ? N15 C22 1.343(4) . ? N15 C23 1.364(4) . ? N16 C22 1.342(4) . ? N16 C24 1.368(4) . ? N16 H16A 0.8600 . ? N17 C25 1.341(4) . ? N17 C27 1.369(4) . ? N18 C25 1.338(4) . ? N18 C26 1.365(5) . ? N18 H18B 0.8600 . ? N19 C28 1.319(4) . ? N19 C29 1.379(4) . ? N20 C28 1.340(4) . ? N20 C30 1.368(4) . ? N20 H20A 0.8600 . ? N21 C31 1.334(4) . ? N21 C32 1.380(4) . ? N22 C31 1.339(4) . ? N22 C33 1.370(4) . ? N22 H22A 0.8600 . ? N23 C34 1.341(4) . ? N23 C35 1.372(4) . ? N24 C34 1.343(4) . ? N24 C36 1.363(4) . ? N24 H24A 0.8600 . ? C1 C4 1.427(4) . ? C2 C3 1.374(4) . ? C2 H2B 0.9300 . ? C3 H3A 0.9300 . ? C5 C6 1.358(5) . ? C5 H5A 0.9300 . ? C6 H6B 0.9300 . ? C7 C10 1.423(4) . ? C8 C9 1.361(5) . ? C8 H8B 0.9300 . ? C9 H9A 0.9300 . ? C11 C12 1.363(5) . ? C11 H11A 0.9300 . ? C12 H12B 0.9300 . ? C13 C16 1.434(5) . ? C14 C15 1.373(5) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C17 C18 1.356(5) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 C22 1.421(4) . ? C20 C21 1.364(5) . ? C20 H20B 0.9300 . ? C21 H21A 0.9300 . ? C23 C24 1.368(5) . ? C23 H23A 0.9300 . ? C24 H24B 0.9300 . ? C25 C28 1.444(4) . ? C26 C27 1.360(5) . ? C26 H26A 0.9300 . ? C27 H27A 0.9300 . ? C29 C30 1.358(5) . ? C29 H29A 0.9300 . ? C30 H30A 0.9300 . ? C31 C34 1.429(4) . ? C32 C33 1.359(5) . ? C32 H32A 0.9300 . ? C33 H33A 0.9300 . ? C35 C36 1.370(5) . ? C35 H35A 0.9300 . ? C36 H36A 0.9300 . ? 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 N3 Co1 N9 90.92(11) . . ? N3 Co1 N7 175.36(11) . . ? N9 Co1 N7 90.87(11) . . ? N3 Co1 N11 94.94(11) . . ? N9 Co1 N11 82.72(11) . . ? N7 Co1 N11 89.53(11) . . ? N3 Co1 N5 92.73(11) . . ? N9 Co1 N5 93.39(11) . . ? N7 Co1 N5 82.90(11) . . ? N11 Co1 N5 171.45(11) . . ? N3 Co1 N1 82.68(11) . . ? N9 Co1 N1 172.07(11) . . ? N7 Co1 N1 95.87(11) . . ? N11 Co1 N1 93.12(11) . . ? N5 Co1 N1 91.60(11) . . ? N13 Co2 N19 92.37(11) . . ? N13 Co2 N15 82.89(11) . . ? N19 Co2 N15 91.87(11) . . ? N13 Co2 N21 174.18(11) . . ? N19 Co2 N21 90.84(11) . . ? N15 Co2 N21 92.16(11) . . ? N13 Co2 N23 94.77(11) . . ? N19 Co2 N23 171.97(11) . . ? N15 Co2 N23 92.66(11) . . ? N21 Co2 N23 82.37(11) . . ? N13 Co2 N17 90.30(11) . . ? N19 Co2 N17 83.00(11) . . ? N15 Co2 N17 171.31(11) . . ? N21 Co2 N17 94.92(11) . . ? N23 Co2 N17 93.27(11) . . ? O1 S1 O4 110.43(18) . . ? O1 S1 O2 110.71(15) . . ? O4 S1 O2 110.87(17) . . ? O1 S1 O3 107.31(19) . . ? O4 S1 O3 108.2(2) . . ? O2 S1 O3 109.18(16) . . ? O5 S2 O6 110.82(14) . . ? O5 S2 O7 109.78(14) . . ? O6 S2 O7 110.35(14) . . ? O5 S2 O8 108.84(15) . . ? O6 S2 O8 109.31(14) . . ? O7 S2 O8 107.68(14) . . ? C1 N1 C3 107.1(3) . . ? C1 N1 Co1 113.8(2) . . ? C3 N1 Co1 139.1(2) . . ? C1 N2 C2 107.6(3) . . ? C1 N2 H2A 126.2 . . ? C2 N2 H2A 126.2 . . ? C4 N3 C5 107.2(3) . . ? C4 N3 Co1 114.0(2) . . ? C5 N3 Co1 138.8(2) . . ? C4 N4 C6 106.9(3) . . ? C4 N4 H4A 126.5 . . ? C6 N4 H4A 126.5 . . ? C7 N5 C8 107.0(3) . . ? C7 N5 Co1 113.3(2) . . ? C8 N5 Co1 139.6(2) . . ? C7 N6 C9 107.3(3) . . ? C7 N6 H6A 126.3 . . ? C9 N6 H6A 126.3 . . ? C10 N7 C11 107.0(3) . . ? C10 N7 Co1 113.6(2) . . ? C11 N7 Co1 139.1(2) . . ? C10 N8 C12 106.8(3) . . ? C10 N8 H8A 126.6 . . ? C12 N8 H8A 126.6 . . ? C13 N9 C14 107.2(3) . . ? C13 N9 Co1 113.8(2) . . ? C14 N9 Co1 138.7(2) . . ? C13 N10 C15 107.2(3) . . ? C13 N10 H10A 126.4 . . ? C15 N10 H10A 126.4 . . ? C16 N11 C17 106.7(3) . . ? C16 N11 Co1 113.7(2) . . ? C17 N11 Co1 137.8(2) . . ? C16 N12 C18 106.9(3) . . ? C16 N12 H12A 126.5 . . ? C18 N12 H12A 126.5 . . ? C19 N13 C20 106.7(3) . . ? C19 N13 Co2 114.0(2) . . ? C20 N13 Co2 139.1(2) . . ? C19 N14 C21 107.6(3) . . ? C19 N14 H14B 126.2 . . ? C21 N14 H14B 126.2 . . ? C22 N15 C23 107.4(3) . . ? C22 N15 Co2 113.3(2) . . ? C23 N15 Co2 139.2(2) . . ? C22 N16 C24 108.0(3) . . ? C22 N16 H16A 126.0 . . ? C24 N16 H16A 126.0 . . ? C25 N17 C27 106.4(3) . . ? C25 N17 Co2 113.0(2) . . ? C27 N17 Co2 139.7(2) . . ? C25 N18 C26 107.4(3) . . ? C25 N18 H18B 126.3 . . ? C26 N18 H18B 126.3 . . ? C28 N19 C29 106.7(3) . . ? C28 N19 Co2 114.6(2) . . ? C29 N19 Co2 138.3(2) . . ? C28 N20 C30 107.0(3) . . ? C28 N20 H20A 126.5 . . ? C30 N20 H20A 126.5 . . ? C31 N21 C32 107.0(3) . . ? C31 N21 Co2 114.6(2) . . ? C32 N21 Co2 138.2(2) . . ? C31 N22 C33 107.4(3) . . ? C31 N22 H22A 126.3 . . ? C33 N22 H22A 126.3 . . ? C34 N23 C35 106.7(3) . . ? C34 N23 Co2 113.9(2) . . ? C35 N23 Co2 139.4(2) . . ? C34 N24 C36 107.7(3) . . ? C34 N24 H24A 126.2 . . ? C36 N24 H24A 126.2 . . ? N2 C1 N1 110.3(3) . . ? N2 C1 C4 135.0(3) . . ? N1 C1 C4 114.6(3) . . ? C3 C2 N2 107.1(3) . . ? C3 C2 H2B 126.5 . . ? N2 C2 H2B 126.5 . . ? N1 C3 C2 107.9(3) . . ? N1 C3 H3A 126.0 . . ? C2 C3 H3A 126.0 . . ? N4 C4 N3 110.2(3) . . ? N4 C4 C1 135.0(3) . . ? N3 C4 C1 114.8(3) . . ? N3 C5 C6 108.6(3) . . ? N3 C5 H5A 125.7 . . ? C6 C5 H5A 125.7 . . ? C5 C6 N4 107.2(3) . . ? C5 C6 H6B 126.4 . . ? N4 C6 H6B 126.4 . . ? N6 C7 N5 110.1(3) . . ? N6 C7 C10 135.4(3) . . ? N5 C7 C10 114.5(3) . . ? C9 C8 N5 108.6(3) . . ? C9 C8 H8B 125.7 . . ? N5 C8 H8B 125.7 . . ? C8 C9 N6 107.0(3) . . ? C8 C9 H9A 126.5 . . ? N6 C9 H9A 126.5 . . ? N7 C10 N8 110.7(3) . . ? N7 C10 C7 115.5(3) . . ? N8 C10 C7 133.7(3) . . ? C12 C11 N7 108.3(3) . . ? C12 C11 H11A 125.9 . . ? N7 C11 H11A 125.9 . . ? C11 C12 N8 107.2(3) . . ? C11 C12 H12B 126.4 . . ? N8 C12 H12B 126.4 . . ? N9 C13 N10 110.4(3) . . ? N9 C13 C16 114.8(3) . . ? N10 C13 C16 134.7(3) . . ? C15 C14 N9 107.3(3) . . ? C15 C14 H14A 126.3 . . ? N9 C14 H14A 126.3 . . ? N10 C15 C14 107.8(3) . . ? N10 C15 H15A 126.1 . . ? C14 C15 H15A 126.1 . . ? N11 C16 N12 110.6(3) . . ? N11 C16 C13 114.4(3) . . ? N12 C16 C13 134.8(3) . . ? C18 C17 N11 108.6(3) . . ? C18 C17 H17A 125.7 . . ? N11 C17 H17A 125.7 . . ? C17 C18 N12 107.3(3) . . ? C17 C18 H18A 126.4 . . ? N12 C18 H18A 126.4 . . ? N13 C19 N14 110.4(3) . . ? N13 C19 C22 114.6(3) . . ? N14 C19 C22 135.0(3) . . ? C21 C20 N13 107.8(3) . . ? C21 C20 H20B 126.1 . . ? N13 C20 H20B 126.1 . . ? C20 C21 N14 107.5(3) . . ? C20 C21 H21A 126.3 . . ? N14 C21 H21A 126.3 . . ? N16 C22 N15 109.4(3) . . ? N16 C22 C19 135.6(3) . . ? N15 C22 C19 115.0(3) . . ? N15 C23 C24 108.2(3) . . ? N15 C23 H23A 125.9 . . ? C24 C23 H23A 125.9 . . ? N16 C24 C23 107.0(3) . . ? N16 C24 H24B 126.5 . . ? C23 C24 H24B 126.5 . . ? N18 C25 N17 110.4(3) . . ? N18 C25 C28 134.4(3) . . ? N17 C25 C28 114.9(3) . . ? C27 C26 N18 107.3(3) . . ? C27 C26 H26A 126.4 . . ? N18 C26 H26A 126.4 . . ? C26 C27 N17 108.5(3) . . ? C26 C27 H27A 125.8 . . ? N17 C27 H27A 125.8 . . ? N19 C28 N20 111.0(3) . . ? N19 C28 C25 114.2(3) . . ? N20 C28 C25 134.7(3) . . ? C30 C29 N19 108.0(3) . . ? C30 C29 H29A 126.0 . . ? N19 C29 H29A 126.0 . . ? C29 C30 N20 107.4(3) . . ? C29 C30 H30A 126.3 . . ? N20 C30 H30A 126.3 . . ? N21 C31 N22 110.3(3) . . ? N21 C31 C34 114.2(3) . . ? N22 C31 C34 135.5(3) . . ? C33 C32 N21 107.7(3) . . ? C33 C32 H32A 126.2 . . ? N21 C32 H32A 126.2 . . ? C32 C33 N22 107.7(3) . . ? C32 C33 H33A 126.2 . . ? N22 C33 H33A 126.2 . . ? N23 C34 N24 110.3(3) . . ? N23 C34 C31 114.7(3) . . ? N24 C34 C31 135.0(3) . . ? C36 C35 N23 108.2(3) . . ? C36 C35 H35A 125.9 . . ? N23 C35 H35A 125.9 . . ? N24 C36 C35 107.2(3) . . ? N24 C36 H36A 126.4 . . ? C35 C36 H36A 126.4 . . ? _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.391 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.108 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.009 0.000 -0.006 1114 254 ' ' 2 -0.026 0.500 0.846 1114 254 ' ' _platon_squeeze_details ; ;