# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_x _database_code_depnum_ccdc_archive 'CCDC 910889' #TrackingRef 'ANPyO.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2.50 H2.50 N2.50 O2.50' _chemical_formula_weight 107.57 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.740(3) _cell_length_b 7.2920(15) _cell_length_c 7.5740(15) _cell_angle_alpha 90.00 _cell_angle_beta 111.61(3) _cell_angle_gamma 90.00 _cell_volume 756.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 14 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.888 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9668 _exptl_absorpt_correction_T_max 0.9832 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius cad4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 1653 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 26.95 _reflns_number_total 831 _reflns_number_gt 658 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 EXPRESS(Enraf-Nonius,1994)' _computing_cell_refinement 'CAD4 EXPRESS' _computing_data_reduction 'XCAD4(Harms & Wocadlo,1995)' _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^+0.4500P] 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 831 _refine_ls_number_parameters 70 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1625 _refine_ls_wR_factor_gt 0.1482 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.010 _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 O1 O 1.0000 0.7280(3) 0.2500 0.0577(7) Uani 1 2 d SU . . C1 C 1.0000 0.1717(4) 0.2500 0.0299(6) Uani 1 2 d S . . H1A H 1.0000 0.0441 0.2500 0.036 Uiso 1 2 calc SR . . N1 N 1.0000 0.5487(3) 0.2500 0.0289(6) Uani 1 2 d SU . . N2 N 0.85694(12) 0.1642(3) -0.0388(2) 0.0376(5) Uani 1 1 d . . . C2 C 0.92865(12) 0.2663(3) 0.1097(2) 0.0296(5) Uani 1 1 d . . . O2 O 0.86367(13) -0.0017(2) -0.0403(3) 0.0618(6) Uani 1 1 d . . . N3 N 0.86128(11) 0.5704(3) -0.0085(2) 0.0380(5) Uani 1 1 d . . . H3A H 0.8675 0.6874 0.0050 0.046 Uiso 1 1 calc R . . H3B H 0.8126 0.5248 -0.1001 0.046 Uiso 1 1 calc R . . C3 C 0.92629(12) 0.4612(3) 0.1110(2) 0.0278(5) Uani 1 1 d . . . O3 O 0.79085(12) 0.2471(2) -0.1617(2) 0.0513(5) 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 O1 0.0666(16) 0.0382(13) 0.0594(16) 0.000 0.0128(13) 0.000 C1 0.0315(13) 0.0262(12) 0.0296(12) 0.000 0.0085(10) 0.000 N1 0.0324(11) 0.0250(11) 0.0261(11) 0.000 0.0071(9) 0.000 N2 0.0330(9) 0.0413(10) 0.0314(9) -0.0070(7) 0.0037(7) -0.0036(7) C2 0.0265(9) 0.0318(10) 0.0249(10) -0.0024(7) 0.0030(8) -0.0024(7) O2 0.0639(12) 0.0320(9) 0.0640(13) -0.0124(8) -0.0064(9) -0.0078(8) N3 0.0363(9) 0.0355(9) 0.0328(9) 0.0062(7) 0.0016(7) 0.0064(7) C3 0.0268(9) 0.0311(10) 0.0236(9) 0.0030(6) 0.0070(7) 0.0033(6) O3 0.0398(9) 0.0576(11) 0.0357(9) -0.0040(7) -0.0105(7) 0.0008(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 O1 N1 1.308(3) . ? C1 C2 1.374(2) 2_755 ? C1 C2 1.374(2) . ? C1 H1A 0.9300 . ? N1 C3 1.362(2) . ? N1 C3 1.362(2) 2_755 ? N2 O2 1.214(3) . ? N2 O3 1.230(2) . ? N2 C2 1.436(2) . ? C2 C3 1.421(3) . ? N3 C3 1.316(2) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? 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 C2 119.7(3) 2_755 . ? C2 C1 H1A 120.2 2_755 . ? C2 C1 H1A 120.2 . . ? O1 N1 C3 117.97(11) . . ? O1 N1 C3 117.97(11) . 2_755 ? C3 N1 C3 124.1(2) . 2_755 ? O2 N2 O3 121.83(17) . . ? O2 N2 C2 119.01(17) . . ? O3 N2 C2 119.16(18) . . ? C1 C2 C3 120.69(18) . . ? C1 C2 N2 118.57(19) . . ? C3 C2 N2 120.74(16) . . ? C3 N3 H3A 120.0 . . ? C3 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? N3 C3 N1 114.79(18) . . ? N3 C3 C2 127.84(17) . . ? N1 C3 C2 117.36(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C2 C3 -1.74(13) 2_755 . . . ? C2 C1 C2 N2 177.87(19) 2_755 . . . ? O2 N2 C2 C1 -2.9(3) . . . . ? O3 N2 C2 C1 177.61(17) . . . . ? O2 N2 C2 C3 176.73(19) . . . . ? O3 N2 C2 C3 -2.8(3) . . . . ? O1 N1 C3 N3 -0.93(18) . . . . ? C3 N1 C3 N3 179.07(18) 2_755 . . . ? O1 N1 C3 C2 178.34(12) . . . . ? C3 N1 C3 C2 -1.66(12) 2_755 . . . ? C1 C2 C3 N3 -177.42(16) . . . . ? N2 C2 C3 N3 3.0(3) . . . . ? C1 C2 C3 N1 3.4(2) . . . . ? N2 C2 C3 N1 -176.18(14) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.95 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.254 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.062 data_x2 _database_code_depnum_ccdc_archive 'CCDC 910890' #TrackingRef 'Co.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H33 Co N18 O18' _chemical_formula_weight 920.61 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.808(2) _cell_length_b 12.955(3) _cell_length_c 14.764(3) _cell_angle_alpha 114.50(3) _cell_angle_beta 93.46(3) _cell_angle_gamma 109.00(3) _cell_volume 1892.4(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 13 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 948 _exptl_absorpt_coefficient_mu 0.554 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9467 _exptl_absorpt_correction_T_max 0.9467 _exptl_absorpt_process_details 'SADABS,2000; Bruker' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius cad4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 7322 _diffrn_reflns_av_R_equivalents 0.0627 _diffrn_reflns_av_sigmaI/netI 0.1315 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.37 _reflns_number_total 6957 _reflns_number_gt 3432 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 EXPRESS(Enraf-Nonius,1994)' _computing_cell_refinement 'CAD4 EXPRESS' _computing_data_reduction 'XCAD4(Harms & Wocadlo,1995)' _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^)+(0.0640P)^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_number_reflns 6957 _refine_ls_number_parameters 550 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1599 _refine_ls_R_factor_gt 0.0780 _refine_ls_wR_factor_ref 0.1739 _refine_ls_wR_factor_gt 0.1462 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 Co Co 0.29991(7) 0.14100(7) 0.84502(6) 0.0321(2) Uani 1 1 d . . . O1 O 0.2468(3) 0.1878(4) 0.7501(3) 0.0404(11) Uani 1 1 d . . . N1 N 0.3469(4) 0.0408(4) 0.7337(4) 0.0377(13) Uani 1 1 d . . . H1A H 0.3899 0.0008 0.7400 0.045 Uiso 1 1 calc R . . C1 C 0.3107(5) 0.0355(5) 0.6464(5) 0.0351(14) Uani 1 1 d . . . N2 N 0.2458(4) 0.1087(4) 0.6536(4) 0.0362(12) Uani 1 1 d . . . C2 C 0.1785(5) 0.1088(6) 0.5740(5) 0.0422(16) Uani 1 1 d . . . O2 O 0.0508(6) 0.0767(5) 0.3985(4) 0.0878(19) Uani 1 1 d . . . C3 C 0.1857(6) 0.0317(6) 0.4761(5) 0.0504(18) Uani 1 1 d . . . N3 N 0.1197(4) 0.1834(5) 0.6005(4) 0.0519(15) Uani 1 1 d . . . H3A H 0.1247 0.2280 0.6641 0.062 Uiso 1 1 calc R . . H3B H 0.0761 0.1876 0.5543 0.062 Uiso 1 1 calc R . . O3 O 0.1311(6) -0.0420(7) 0.3038(4) 0.110(2) Uani 1 1 d . . . O4 O 0.4143(5) -0.1513(5) 0.4411(4) 0.0850(18) Uani 1 1 d . . . N4 N 0.1196(6) 0.0228(7) 0.3880(5) 0.0650(18) Uani 1 1 d . . . C4 C 0.2585(6) -0.0339(6) 0.4644(5) 0.0488(18) Uani 1 1 d . . . H4A H 0.2662 -0.0800 0.3990 0.059 Uiso 1 1 calc R . . N5 N 0.3962(5) -0.1021(6) 0.5286(5) 0.0625(17) Uani 1 1 d . . . C5 C 0.3210(6) -0.0340(6) 0.5459(5) 0.0465(17) Uani 1 1 d . . . O5 O 0.4462(5) -0.1068(5) 0.6021(4) 0.0870(19) Uani 1 1 d . . . O6 O 0.4545(3) 0.2758(3) 0.8943(3) 0.0354(10) Uani 1 1 d . . . N6 N 0.3684(4) 0.1055(4) 0.9395(3) 0.0328(12) Uani 1 1 d . . . H6A H 0.3368 0.0352 0.9389 0.039 Uiso 1 1 calc R . . C6 C 0.4666(5) 0.1930(5) 1.0065(4) 0.0323(14) Uani 1 1 d . . . N7 N 0.5130(4) 0.2888(4) 0.9839(3) 0.0316(11) Uani 1 1 d . . . O7 O 0.8175(4) 0.5959(4) 1.1773(4) 0.0662(14) Uani 1 1 d . . . C7 C 0.6107(5) 0.3975(5) 1.0434(4) 0.0322(14) Uani 1 1 d . . . N8 N 0.6365(4) 0.4788(4) 1.0092(4) 0.0455(14) Uani 1 1 d . . . H8A H 0.5932 0.4624 0.9524 0.055 Uiso 1 1 calc R . . H8B H 0.6969 0.5487 1.0434 0.055 Uiso 1 1 calc R . . C8 C 0.6698(5) 0.4055(5) 1.1342(5) 0.0384(15) Uani 1 1 d . . . O8 O 0.8101(5) 0.5244(4) 1.2873(4) 0.0802(18) Uani 1 1 d . . . C9 C 0.6301(5) 0.3110(5) 1.1581(5) 0.0403(16) Uani 1 1 d . . . H9A H 0.6717 0.3193 1.2178 0.048 Uiso 1 1 calc R . . N9 N 0.7716(5) 0.5146(5) 1.2035(5) 0.0531(15) Uani 1 1 d . . . O9 O 0.5505(4) 0.1271(4) 1.2086(4) 0.0685(15) Uani 1 1 d . . . C10 C 0.5309(5) 0.2036(5) 1.0975(4) 0.0354(14) Uani 1 1 d . . . O10 O 0.4076(4) 0.0122(4) 1.0693(3) 0.0505(12) Uani 1 1 d . . . N10 N 0.4951(5) 0.1109(5) 1.1267(4) 0.0463(14) Uani 1 1 d . . . N11 N 0.1404(4) 0.0240(4) 0.8179(4) 0.0410(13) Uani 1 1 d . . . H11A H 0.1141 -0.0498 0.7690 0.049 Uiso 1 1 calc R . . O11 O 0.2445(3) 0.2456(3) 0.9467(3) 0.0395(10) Uani 1 1 d . . . C11 C 0.0746(5) 0.0643(6) 0.8789(5) 0.0348(14) Uani 1 1 d . . . C12 C 0.0845(5) 0.2452(6) 1.0303(5) 0.0396(15) Uani 1 1 d . . . N12 N 0.1301(4) 0.1828(4) 0.9528(4) 0.0400(13) Uani 1 1 d . . . O12 O -0.0454(5) 0.3472(5) 1.1649(4) 0.0816(17) Uani 1 1 d . . . N13 N 0.1598(5) 0.3575(4) 1.0958(4) 0.0524(15) Uani 1 1 d . . . H13A H 0.2330 0.3871 1.0880 0.063 Uiso 1 1 calc R . . H13B H 0.1359 0.4014 1.1465 0.063 Uiso 1 1 calc R . . C13 C -0.0366(5) 0.1812(6) 1.0298(5) 0.0408(15) Uani 1 1 d . . . O13 O -0.1965(4) 0.1724(4) 1.1121(4) 0.0687(15) Uani 1 1 d . . . C14 C -0.1032(5) 0.0607(6) 0.9548(5) 0.0441(17) Uani 1 1 d . . . H14A H -0.1844 0.0205 0.9547 0.053 Uiso 1 1 calc R . . O14 O -0.0719(4) -0.1846(4) 0.7536(4) 0.0664(15) Uani 1 1 d . . . N14 N -0.0964(5) 0.2362(6) 1.1056(5) 0.0601(17) Uani 1 1 d . . . C15 C -0.0514(5) 0.0032(5) 0.8834(5) 0.0378(15) Uani 1 1 d . . . O16 O 0.0477(6) -0.2536(7) 0.4890(6) 0.123(3) Uani 1 1 d . . . N16 N 0.1373(6) -0.3685(6) 0.5069(6) 0.0742(19) Uani 1 1 d . . . N15 N -0.1225(5) -0.1216(5) 0.8098(5) 0.0550(16) Uani 1 1 d . . . O15 O -0.2332(4) -0.1636(5) 0.8064(5) 0.102(2) Uani 1 1 d . . . C16 C 0.1865(11) -0.4594(11) 0.4603(10) 0.172(6) Uani 1 1 d . . . H16A H 0.1677 -0.4898 0.3875 0.259 Uiso 1 1 calc R . . H16B H 0.1510 -0.5259 0.4764 0.259 Uiso 1 1 calc R . . H16C H 0.2741 -0.4238 0.4855 0.259 Uiso 1 1 calc R . . C17 C 0.1559(10) -0.3138(9) 0.6137(7) 0.150(5) Uani 1 1 d . . . H17A H 0.1192 -0.2539 0.6358 0.225 Uiso 1 1 calc R . . H17B H 0.2425 -0.2742 0.6439 0.225 Uiso 1 1 calc R . . H17C H 0.1186 -0.3758 0.6344 0.225 Uiso 1 1 calc R . . C18 C 0.0848(8) -0.3328(9) 0.4529(7) 0.080(3) Uani 1 1 d . . . H18A H 0.0758 -0.3712 0.3824 0.096 Uiso 1 1 calc R . . O17 O 0.7854(7) 0.4024(5) 0.7543(4) 0.104(2) Uani 1 1 d . . . N17 N 0.7843(6) 0.2830(6) 0.8300(5) 0.0660(18) Uani 1 1 d . . . C19 C 0.9127(8) 0.3343(10) 0.8674(10) 0.159(6) Uani 1 1 d . . . H19A H 0.9495 0.3982 0.8486 0.239 Uiso 1 1 calc R . . H19B H 0.9449 0.2716 0.8387 0.239 Uiso 1 1 calc R . . H19C H 0.9311 0.3682 0.9406 0.239 Uiso 1 1 calc R . . C20 C 0.7100(7) 0.1828(7) 0.8496(7) 0.088(3) Uani 1 1 d . . . H20A H 0.6249 0.1566 0.8195 0.133 Uiso 1 1 calc R . . H20B H 0.7208 0.2109 0.9220 0.133 Uiso 1 1 calc R . . H20C H 0.7356 0.1151 0.8201 0.133 Uiso 1 1 calc R . . C21 C 0.7310(8) 0.3215(7) 0.7763(6) 0.074(2) Uani 1 1 d . . . H21A H 0.6459 0.2841 0.7536 0.089 Uiso 1 1 calc R . . O18 O 0.5661(4) 0.5109(5) 0.8391(4) 0.0671(14) Uani 1 1 d . . . N18 N 0.4973(5) 0.4523(6) 0.6728(5) 0.0641(18) Uani 1 1 d . . . C22 C 0.4282(8) 0.3542(8) 0.5733(7) 0.117(4) Uani 1 1 d . . . H22A H 0.3889 0.2799 0.5783 0.176 Uiso 1 1 calc R . . H22B H 0.4827 0.3423 0.5277 0.176 Uiso 1 1 calc R . . H22C H 0.3669 0.3751 0.5475 0.176 Uiso 1 1 calc R . . C23 C 0.5643(9) 0.5690(8) 0.6787(7) 0.120(4) Uani 1 1 d . . . H23A H 0.6059 0.6270 0.7483 0.180 Uiso 1 1 calc R . . H23B H 0.5086 0.5968 0.6545 0.180 Uiso 1 1 calc R . . H23C H 0.6236 0.5619 0.6371 0.180 Uiso 1 1 calc R . . C24 C 0.5072(7) 0.4342(8) 0.7522(7) 0.070(2) Uani 1 1 d . . . H24A H 0.4653 0.3545 0.7423 0.083 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 Co 0.0223(4) 0.0344(5) 0.0336(5) 0.0168(4) -0.0002(3) 0.0036(3) O1 0.033(2) 0.044(3) 0.039(3) 0.020(2) 0.000(2) 0.009(2) N1 0.027(3) 0.041(3) 0.042(3) 0.020(3) -0.007(2) 0.012(2) C1 0.023(3) 0.041(4) 0.038(4) 0.018(3) 0.000(3) 0.009(3) N2 0.029(3) 0.043(3) 0.036(3) 0.024(3) 0.000(2) 0.007(2) C2 0.034(4) 0.049(4) 0.040(4) 0.028(3) 0.000(3) 0.003(3) O2 0.102(5) 0.092(4) 0.066(4) 0.029(3) -0.009(3) 0.048(4) C3 0.043(4) 0.063(5) 0.039(4) 0.030(4) -0.003(3) 0.007(4) N3 0.036(3) 0.045(3) 0.064(4) 0.026(3) -0.010(3) 0.006(3) O3 0.141(6) 0.161(6) 0.041(3) 0.041(4) 0.012(4) 0.082(5) O4 0.095(4) 0.100(4) 0.050(3) 0.015(3) 0.022(3) 0.050(4) N4 0.058(4) 0.085(5) 0.058(5) 0.043(4) 0.007(4) 0.023(4) C4 0.039(4) 0.060(5) 0.038(4) 0.020(3) -0.002(3) 0.013(4) N5 0.050(4) 0.070(4) 0.060(4) 0.025(4) 0.012(3) 0.021(3) C5 0.034(4) 0.042(4) 0.048(4) 0.012(3) 0.004(3) 0.007(3) O5 0.107(5) 0.115(5) 0.057(4) 0.034(3) 0.008(3) 0.074(4) O6 0.030(2) 0.042(2) 0.036(2) 0.027(2) -0.0010(19) 0.0060(19) N6 0.023(3) 0.022(2) 0.041(3) 0.016(2) 0.001(2) -0.007(2) C6 0.019(3) 0.040(4) 0.034(3) 0.015(3) 0.003(3) 0.010(3) N7 0.022(3) 0.037(3) 0.034(3) 0.017(2) 0.004(2) 0.008(2) O7 0.048(3) 0.050(3) 0.075(4) 0.024(3) -0.008(3) -0.001(2) C7 0.025(3) 0.035(3) 0.037(4) 0.018(3) 0.007(3) 0.009(3) N8 0.037(3) 0.042(3) 0.048(3) 0.024(3) -0.001(3) 0.001(3) C8 0.023(3) 0.039(4) 0.043(4) 0.015(3) -0.012(3) 0.009(3) O8 0.073(4) 0.048(3) 0.075(4) 0.013(3) -0.041(3) 0.001(3) C9 0.032(4) 0.047(4) 0.043(4) 0.020(3) -0.005(3) 0.020(3) N9 0.042(4) 0.042(3) 0.061(4) 0.017(3) -0.010(3) 0.011(3) O9 0.071(3) 0.069(3) 0.057(3) 0.040(3) -0.015(3) 0.007(3) C10 0.032(3) 0.037(3) 0.038(4) 0.020(3) 0.003(3) 0.011(3) O10 0.040(3) 0.052(3) 0.063(3) 0.037(3) 0.002(2) 0.010(2) N10 0.036(3) 0.044(3) 0.051(4) 0.022(3) 0.003(3) 0.007(3) N11 0.037(3) 0.034(3) 0.038(3) 0.011(2) -0.003(3) 0.006(2) O11 0.027(2) 0.035(2) 0.041(2) 0.015(2) 0.0044(19) -0.0033(19) C11 0.024(3) 0.046(4) 0.039(4) 0.026(3) 0.002(3) 0.011(3) C12 0.026(3) 0.039(4) 0.051(4) 0.028(3) 0.003(3) 0.001(3) N12 0.029(3) 0.036(3) 0.044(3) 0.018(3) 0.004(3) 0.001(2) O12 0.061(3) 0.063(4) 0.093(4) 0.017(3) 0.037(3) 0.013(3) N13 0.042(3) 0.043(3) 0.051(4) 0.009(3) 0.015(3) 0.007(3) C13 0.030(3) 0.041(4) 0.051(4) 0.022(3) 0.013(3) 0.011(3) O13 0.041(3) 0.063(3) 0.094(4) 0.036(3) 0.027(3) 0.009(3) C14 0.024(3) 0.051(4) 0.063(5) 0.037(4) 0.011(3) 0.007(3) O14 0.052(3) 0.047(3) 0.066(4) 0.013(3) -0.001(3) -0.003(3) N14 0.047(4) 0.060(4) 0.069(4) 0.033(4) 0.011(3) 0.012(3) C15 0.028(3) 0.036(4) 0.043(4) 0.020(3) 0.000(3) 0.003(3) O16 0.102(6) 0.111(6) 0.163(7) 0.070(6) -0.016(5) 0.047(5) N16 0.056(4) 0.078(5) 0.096(6) 0.049(5) 0.008(4) 0.027(4) N15 0.033(3) 0.040(4) 0.067(4) 0.022(3) 0.003(3) -0.009(3) O15 0.035(3) 0.064(4) 0.129(5) 0.007(4) 0.012(3) -0.021(3) C16 0.166(13) 0.178(13) 0.267(18) 0.134(13) 0.110(12) 0.125(12) C17 0.179(12) 0.119(9) 0.082(8) 0.051(7) -0.057(8) -0.015(8) C18 0.072(6) 0.084(7) 0.089(7) 0.051(6) 0.005(5) 0.025(5) O17 0.170(7) 0.060(4) 0.078(4) 0.032(3) 0.040(4) 0.036(4) N17 0.054(4) 0.068(4) 0.082(5) 0.042(4) 0.017(4) 0.021(4) C19 0.053(7) 0.167(11) 0.264(16) 0.144(12) -0.006(8) -0.002(7) C20 0.083(6) 0.086(6) 0.115(8) 0.063(6) 0.039(6) 0.031(5) C21 0.088(7) 0.055(5) 0.068(6) 0.021(5) 0.021(5) 0.023(5) O18 0.055(3) 0.070(4) 0.068(4) 0.035(3) 0.011(3) 0.010(3) N18 0.053(4) 0.077(5) 0.056(4) 0.038(4) 0.005(3) 0.010(3) C22 0.100(8) 0.104(8) 0.094(8) 0.045(7) 0.000(6) -0.020(6) C23 0.134(9) 0.074(7) 0.132(9) 0.061(7) 0.042(7) -0.003(6) C24 0.050(5) 0.070(6) 0.079(6) 0.038(5) 0.004(5) 0.009(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 Co N6 1.858(4) . ? Co N1 1.872(5) . ? Co O11 1.877(4) . ? Co N11 1.885(5) . ? Co O1 1.889(4) . ? Co O6 1.903(4) . ? O1 N2 1.364(6) . ? N1 C1 1.300(7) . ? N1 H1A 0.8600 . ? C1 N2 1.377(7) . ? C1 C5 1.419(8) . ? N2 C2 1.379(7) . ? C2 N3 1.314(8) . ? C2 C3 1.402(9) . ? O2 N4 1.212(7) . ? C3 C4 1.365(9) . ? C3 N4 1.418(8) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? O3 N4 1.225(8) . ? O4 N5 1.248(7) . ? C4 C5 1.373(8) . ? C4 H4A 0.9300 . ? N5 O5 1.238(7) . ? N5 C5 1.408(8) . ? O6 N7 1.372(5) . ? N6 C6 1.297(6) . ? N6 H6A 0.8600 . ? C6 N7 1.370(7) . ? C6 C10 1.433(7) . ? N7 C7 1.371(7) . ? O7 N9 1.243(6) . ? C7 N8 1.308(7) . ? C7 C8 1.421(7) . ? N8 H8A 0.8600 . ? N8 H8B 0.8600 . ? C8 C9 1.360(8) . ? C8 N9 1.426(7) . ? O8 N9 1.231(7) . ? C9 C10 1.374(7) . ? C9 H9A 0.9300 . ? O9 N10 1.240(6) . ? C10 N10 1.390(7) . ? O10 N10 1.247(6) . ? N11 C11 1.282(7) . ? N11 H11A 0.8600 . ? O11 N12 1.362(5) . ? C11 N12 1.358(7) . ? C11 C15 1.461(8) . ? C12 N13 1.315(7) . ? C12 N12 1.358(8) . ? C12 C13 1.398(8) . ? O12 N14 1.235(7) . ? N13 H13A 0.8600 . ? N13 H13B 0.8600 . ? C13 C14 1.394(8) . ? C13 N14 1.422(8) . ? O13 N14 1.238(6) . ? C14 C15 1.329(8) . ? C14 H14A 0.9300 . ? O14 N15 1.236(7) . ? C15 N15 1.431(7) . ? O16 C18 1.182(10) . ? N16 C18 1.290(10) . ? N16 C17 1.402(11) . ? N16 C16 1.421(11) . ? N15 O15 1.231(6) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9300 . ? O17 C21 1.219(9) . ? N17 C21 1.321(9) . ? N17 C19 1.408(9) . ? N17 C20 1.463(9) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9300 . ? O18 C24 1.225(8) . ? N18 C24 1.294(9) . ? N18 C23 1.422(9) . ? N18 C22 1.439(9) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 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 N6 Co N1 95.8(2) . . ? N6 Co O11 90.46(19) . . ? N1 Co O11 173.74(19) . . ? N6 Co N11 94.73(19) . . ? N1 Co N11 95.9(2) . . ? O11 Co N11 83.4(2) . . ? N6 Co O1 174.13(18) . . ? N1 Co O1 82.94(19) . . ? O11 Co O1 90.86(18) . . ? N11 Co O1 91.11(18) . . ? N6 Co O6 82.81(17) . . ? N1 Co O6 94.10(19) . . ? O11 Co O6 86.83(17) . . ? N11 Co O6 169.9(2) . . ? O1 Co O6 91.55(16) . . ? N2 O1 Co 110.0(3) . . ? C1 N1 Co 115.8(4) . . ? C1 N1 H1A 122.1 . . ? Co N1 H1A 122.1 . . ? N1 C1 N2 112.8(6) . . ? N1 C1 C5 132.5(6) . . ? N2 C1 C5 114.6(5) . . ? O1 N2 C2 116.9(5) . . ? O1 N2 C1 116.1(5) . . ? C2 N2 C1 127.0(6) . . ? N3 C2 N2 115.6(6) . . ? N3 C2 C3 129.2(6) . . ? N2 C2 C3 115.2(6) . . ? C4 C3 C2 120.5(6) . . ? C4 C3 N4 119.0(7) . . ? C2 C3 N4 120.5(7) . . ? C2 N3 H3A 120.0 . . ? C2 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? O2 N4 O3 122.2(7) . . ? O2 N4 C3 118.8(7) . . ? O3 N4 C3 118.9(7) . . ? C3 C4 C5 122.3(7) . . ? C3 C4 H4A 118.9 . . ? C5 C4 H4A 118.9 . . ? O5 N5 O4 122.3(7) . . ? O5 N5 C5 118.4(7) . . ? O4 N5 C5 119.3(7) . . ? C4 C5 N5 119.3(7) . . ? C4 C5 C1 119.9(6) . . ? N5 C5 C1 120.7(6) . . ? N7 O6 Co 108.8(3) . . ? C6 N6 Co 116.1(4) . . ? C6 N6 H6A 122.0 . . ? Co N6 H6A 122.0 . . ? N6 C6 N7 112.5(5) . . ? N6 C6 C10 130.4(5) . . ? N7 C6 C10 117.1(5) . . ? C7 N7 O6 117.0(4) . . ? C7 N7 C6 126.0(5) . . ? O6 N7 C6 116.9(4) . . ? N8 C7 N7 116.0(5) . . ? N8 C7 C8 129.1(5) . . ? N7 C7 C8 114.9(5) . . ? C7 N8 H8A 120.0 . . ? C7 N8 H8B 120.0 . . ? H8A N8 H8B 120.0 . . ? C9 C8 C7 121.2(5) . . ? C9 C8 N9 118.4(5) . . ? C7 C8 N9 120.4(5) . . ? C8 C9 C10 122.6(5) . . ? C8 C9 H9A 118.7 . . ? C10 C9 H9A 118.7 . . ? O8 N9 O7 122.7(6) . . ? O8 N9 C8 118.4(6) . . ? O7 N9 C8 118.9(6) . . ? C9 C10 N10 119.5(5) . . ? C9 C10 C6 118.1(5) . . ? N10 C10 C6 122.4(5) . . ? O9 N10 O10 121.3(5) . . ? O9 N10 C10 119.8(5) . . ? O10 N10 C10 118.9(5) . . ? C11 N11 Co 114.1(4) . . ? C11 N11 H11A 123.0 . . ? Co N11 H11A 123.0 . . ? N12 O11 Co 111.1(3) . . ? N11 C11 N12 115.8(5) . . ? N11 C11 C15 130.7(6) . . ? N12 C11 C15 113.6(6) . . ? N13 C12 N12 115.9(5) . . ? N13 C12 C13 128.6(6) . . ? N12 C12 C13 115.5(6) . . ? C12 N12 O11 116.9(5) . . ? C12 N12 C11 127.8(5) . . ? O11 N12 C11 115.3(5) . . ? C12 N13 H13A 120.0 . . ? C12 N13 H13B 120.0 . . ? H13A N13 H13B 120.0 . . ? C14 C13 C12 121.1(6) . . ? C14 C13 N14 117.5(6) . . ? C12 C13 N14 121.4(6) . . ? C15 C14 C13 120.4(6) . . ? C15 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? O12 N14 O13 121.6(7) . . ? O12 N14 C13 118.6(6) . . ? O13 N14 C13 119.8(6) . . ? C14 C15 N15 118.2(6) . . ? C14 C15 C11 121.6(6) . . ? N15 C15 C11 120.2(6) . . ? C18 N16 C17 121.8(9) . . ? C18 N16 C16 120.7(9) . . ? C17 N16 C16 117.4(9) . . ? O15 N15 O14 122.0(6) . . ? O15 N15 C15 118.0(6) . . ? O14 N15 C15 120.0(6) . . ? N16 C16 H16A 109.5 . . ? N16 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N16 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N16 C17 H17A 109.5 . . ? N16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O16 C18 N16 123.0(10) . . ? O16 C18 H18A 118.5 . . ? N16 C18 H18A 118.5 . . ? C21 N17 C19 121.5(8) . . ? C21 N17 C20 120.0(7) . . ? C19 N17 C20 118.5(7) . . ? N17 C19 H19A 109.5 . . ? N17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N17 C20 H20A 109.5 . . ? N17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O17 C21 N17 124.7(9) . . ? O17 C21 H21A 117.6 . . ? N17 C21 H21A 117.6 . . ? C24 N18 C23 120.8(7) . . ? C24 N18 C22 122.1(7) . . ? C23 N18 C22 116.8(7) . . ? N18 C22 H22A 109.5 . . ? N18 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N18 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N18 C23 H23A 109.5 . . ? N18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O18 C24 N18 126.8(8) . . ? O18 C24 H24A 116.6 . . ? N18 C24 H24A 116.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N6 Co O1 N2 91(2) . . . . ? N1 Co O1 N2 13.0(3) . . . . ? O11 Co O1 N2 -166.2(3) . . . . ? N11 Co O1 N2 -82.9(3) . . . . ? O6 Co O1 N2 106.9(3) . . . . ? N6 Co N1 C1 177.4(4) . . . . ? O11 Co N1 C1 -1.1(19) . . . . ? N11 Co N1 C1 82.0(4) . . . . ? O1 Co N1 C1 -8.4(4) . . . . ? O6 Co N1 C1 -99.4(4) . . . . ? Co N1 C1 N2 1.5(6) . . . . ? Co N1 C1 C5 -175.7(5) . . . . ? Co O1 N2 C2 162.6(4) . . . . ? Co O1 N2 C1 -16.2(5) . . . . ? N1 C1 N2 O1 10.0(7) . . . . ? C5 C1 N2 O1 -172.3(4) . . . . ? N1 C1 N2 C2 -168.7(5) . . . . ? C5 C1 N2 C2 9.1(8) . . . . ? O1 N2 C2 N3 -1.8(7) . . . . ? C1 N2 C2 N3 176.8(5) . . . . ? O1 N2 C2 C3 176.4(5) . . . . ? C1 N2 C2 C3 -5.0(8) . . . . ? N3 C2 C3 C4 175.8(6) . . . . ? N2 C2 C3 C4 -2.1(9) . . . . ? N3 C2 C3 N4 -2.7(10) . . . . ? N2 C2 C3 N4 179.4(5) . . . . ? C4 C3 N4 O2 176.7(6) . . . . ? C2 C3 N4 O2 -4.7(10) . . . . ? C4 C3 N4 O3 -1.1(10) . . . . ? C2 C3 N4 O3 177.4(7) . . . . ? C2 C3 C4 C5 4.3(10) . . . . ? N4 C3 C4 C5 -177.1(6) . . . . ? C3 C4 C5 N5 -179.0(6) . . . . ? C3 C4 C5 C1 0.1(10) . . . . ? O5 N5 C5 C4 -175.9(6) . . . . ? O4 N5 C5 C4 6.9(9) . . . . ? O5 N5 C5 C1 5.0(9) . . . . ? O4 N5 C5 C1 -172.2(6) . . . . ? N1 C1 C5 C4 170.9(6) . . . . ? N2 C1 C5 C4 -6.3(8) . . . . ? N1 C1 C5 N5 -10.0(10) . . . . ? N2 C1 C5 N5 172.8(5) . . . . ? N6 Co O6 N7 -14.8(3) . . . . ? N1 Co O6 N7 -110.2(3) . . . . ? O11 Co O6 N7 76.0(3) . . . . ? N11 Co O6 N7 61.7(12) . . . . ? O1 Co O6 N7 166.8(3) . . . . ? N1 Co N6 C6 108.0(4) . . . . ? O11 Co N6 C6 -72.1(4) . . . . ? N11 Co N6 C6 -155.5(4) . . . . ? O1 Co N6 C6 31(2) . . . . ? O6 Co N6 C6 14.6(4) . . . . ? Co N6 C6 N7 -10.2(6) . . . . ? Co N6 C6 C10 169.5(5) . . . . ? Co O6 N7 C7 -164.5(4) . . . . ? Co O6 N7 C6 14.1(5) . . . . ? N6 C6 N7 C7 175.3(5) . . . . ? C10 C6 N7 C7 -4.4(8) . . . . ? N6 C6 N7 O6 -3.1(7) . . . . ? C10 C6 N7 O6 177.1(5) . . . . ? O6 N7 C7 N8 1.2(7) . . . . ? C6 N7 C7 N8 -177.3(5) . . . . ? O6 N7 C7 C8 -178.7(5) . . . . ? C6 N7 C7 C8 2.8(8) . . . . ? N8 C7 C8 C9 180.0(6) . . . . ? N7 C7 C8 C9 -0.1(9) . . . . ? N8 C7 C8 N9 1.0(10) . . . . ? N7 C7 C8 N9 -179.1(5) . . . . ? C7 C8 C9 C10 -0.7(10) . . . . ? N9 C8 C9 C10 178.3(6) . . . . ? C9 C8 N9 O8 -8.3(9) . . . . ? C7 C8 N9 O8 170.7(6) . . . . ? C9 C8 N9 O7 171.9(6) . . . . ? C7 C8 N9 O7 -9.1(9) . . . . ? C8 C9 C10 N10 -179.8(6) . . . . ? C8 C9 C10 C6 -0.9(9) . . . . ? N6 C6 C10 C9 -176.4(6) . . . . ? N7 C6 C10 C9 3.3(8) . . . . ? N6 C6 C10 N10 2.4(10) . . . . ? N7 C6 C10 N10 -177.9(5) . . . . ? C9 C10 N10 O9 2.2(9) . . . . ? C6 C10 N10 O9 -176.6(6) . . . . ? C9 C10 N10 O10 -177.6(5) . . . . ? C6 C10 N10 O10 3.6(9) . . . . ? N6 Co N11 C11 87.2(4) . . . . ? N1 Co N11 C11 -176.4(4) . . . . ? O11 Co N11 C11 -2.7(4) . . . . ? O1 Co N11 C11 -93.4(4) . . . . ? O6 Co N11 C11 11.8(13) . . . . ? N6 Co O11 N12 -89.4(3) . . . . ? N1 Co O11 N12 89.1(17) . . . . ? N11 Co O11 N12 5.3(3) . . . . ? O1 Co O11 N12 96.3(3) . . . . ? O6 Co O11 N12 -172.2(3) . . . . ? Co N11 C11 N12 -0.6(6) . . . . ? Co N11 C11 C15 -179.7(5) . . . . ? N13 C12 N12 O11 -4.7(8) . . . . ? C13 C12 N12 O11 175.3(5) . . . . ? N13 C12 N12 C11 176.0(5) . . . . ? C13 C12 N12 C11 -4.0(9) . . . . ? Co O11 N12 C12 173.5(4) . . . . ? Co O11 N12 C11 -7.1(5) . . . . ? N11 C11 N12 C12 -175.5(5) . . . . ? C15 C11 N12 C12 3.7(8) . . . . ? N11 C11 N12 O11 5.2(7) . . . . ? C15 C11 N12 O11 -175.5(4) . . . . ? N13 C12 C13 C14 -179.0(6) . . . . ? N12 C12 C13 C14 1.0(9) . . . . ? N13 C12 C13 N14 1.1(10) . . . . ? N12 C12 C13 N14 -179.0(5) . . . . ? C12 C13 C14 C15 1.8(9) . . . . ? N14 C13 C14 C15 -178.3(6) . . . . ? C14 C13 N14 O12 -170.9(6) . . . . ? C12 C13 N14 O12 9.1(10) . . . . ? C14 C13 N14 O13 10.4(9) . . . . ? C12 C13 N14 O13 -169.7(6) . . . . ? C13 C14 C15 N15 178.2(5) . . . . ? C13 C14 C15 C11 -1.9(9) . . . . ? N11 C11 C15 C14 178.5(6) . . . . ? N12 C11 C15 C14 -0.6(8) . . . . ? N11 C11 C15 N15 -1.6(10) . . . . ? N12 C11 C15 N15 179.3(5) . . . . ? C14 C15 N15 O15 10.8(9) . . . . ? C11 C15 N15 O15 -169.1(6) . . . . ? C14 C15 N15 O14 -167.6(6) . . . . ? C11 C15 N15 O14 12.5(9) . . . . ? C17 N16 C18 O16 -1.0(14) . . . . ? C16 N16 C18 O16 -176.4(10) . . . . ? C19 N17 C21 O17 0.0(14) . . . . ? C20 N17 C21 O17 -178.4(7) . . . . ? C23 N18 C24 O18 4.1(14) . . . . ? C22 N18 C24 O18 178.2(8) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.382 _refine_diff_density_min -0.512 _refine_diff_density_rms 0.086 data_q _database_code_depnum_ccdc_archive 'CCDC 910891' #TrackingRef 'Fe.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H34 Fe N18 O18.50' _chemical_formula_weight 926.54 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.715(2) _cell_length_b 12.900(3) _cell_length_c 14.978(3) _cell_angle_alpha 68.45(3) _cell_angle_beta 89.43(3) _cell_angle_gamma 73.76(3) _cell_volume 2010.4(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 12 _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 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 956 _exptl_absorpt_coefficient_mu 0.472 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9116 _exptl_absorpt_correction_T_max 0.9543 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 7728 _diffrn_reflns_av_R_equivalents 0.0729 _diffrn_reflns_av_sigmaI/netI 0.1204 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.37 _reflns_number_total 7338 _reflns_number_gt 3601 _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^)+(0.0580P)^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_number_reflns 7338 _refine_ls_number_parameters 559 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1680 _refine_ls_R_factor_gt 0.0763 _refine_ls_wR_factor_ref 0.1669 _refine_ls_wR_factor_gt 0.1336 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.002 _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 Fe Fe 0.18752(6) -0.04374(6) 0.62902(5) 0.0428(2) Uani 1 1 d U . . N1 N 0.0352(4) 0.1873(4) 0.5947(3) 0.0552(12) Uani 1 1 d . . . C1 C -0.0458(7) 0.2824(5) 0.5424(5) 0.090(2) Uani 1 1 d . . . O1 O -0.2000(9) 0.5107(8) 0.4405(7) 0.204(4) Uani 1 1 d . . . N2 N -0.1282(5) 0.2784(4) 0.4848(3) 0.092(2) Uani 1 1 d . . . H2A H -0.1279 0.2128 0.4823 0.111 Uiso 1 1 calc R . . H2B H -0.1821 0.3415 0.4500 0.111 Uiso 1 1 calc R . . O2 O -0.1277(9) 0.5792(8) 0.5325(7) 0.223(4) Uani 1 1 d . . . C2 C -0.0502(7) 0.3813(7) 0.5633(5) 0.088(2) Uani 1 1 d U . . C3 C 0.0253(6) 0.3747(6) 0.6396(5) 0.087(2) Uani 1 1 d . . . H3A H 0.0215 0.4404 0.6531 0.104 Uiso 1 1 calc R . . O3 O 0.1680(7) 0.3464(5) 0.7890(4) 0.166(3) Uani 1 1 d . . . N3 N -0.1295(11) 0.4932(11) 0.5111(9) 0.169(4) Uani 1 1 d U . . O4 O 0.2513(5) 0.1683(5) 0.8182(3) 0.0963(17) Uani 1 1 d . . . N4 N 0.1805(6) 0.2584(6) 0.7706(4) 0.0873(19) Uani 1 1 d . . . C4 C 0.1050(7) 0.2671(6) 0.6936(5) 0.085(2) Uani 1 1 d . . . O5 O 0.6122(4) -0.1633(4) 0.6201(3) 0.0772(13) Uani 1 1 d . . . N5 N 0.2895(4) -0.0722(4) 0.4613(3) 0.0520(11) Uani 1 1 d . . . C5 C 0.1162(5) 0.1683(5) 0.6677(4) 0.0526(14) Uani 1 1 d . . . O6 O 0.7074(3) -0.2034(3) 0.5079(3) 0.0701(12) Uani 1 1 d . . . C6 C 0.3906(5) -0.0995(4) 0.5211(4) 0.0453(12) Uani 1 1 d . . . N6 N 0.1789(4) -0.0340(4) 0.3231(3) 0.0687(14) Uani 1 1 d . . . H6A H 0.1167 -0.0144 0.3511 0.082 Uiso 1 1 calc R . . H6B H 0.1710 -0.0303 0.2649 0.082 Uiso 1 1 calc R . . O7 O 0.5067(5) -0.1585(5) 0.2222(3) 0.1112(19) Uani 1 1 d . . . C7 C 0.4977(5) -0.1352(5) 0.4866(4) 0.0542(14) Uani 1 1 d . . . N7 N 0.4043(6) -0.1152(6) 0.2432(4) 0.0873(19) Uani 1 1 d . . . N8 N 0.6127(4) -0.1708(4) 0.5389(4) 0.0647(14) Uani 1 1 d . . . O8 O 0.3147(5) -0.0785(6) 0.1903(4) 0.122(2) Uani 1 1 d . . . C8 C 0.5017(5) -0.1398(5) 0.3947(4) 0.0690(17) Uani 1 1 d . . . H8A H 0.5749 -0.1657 0.3731 0.083 Uiso 1 1 calc R . . N9 N 0.0785(4) -0.2252(4) 0.7202(3) 0.0477(11) Uani 1 1 d . . . O9 O 0.3477(4) -0.3404(4) 0.9387(3) 0.0961(17) Uani 1 1 d . . . C9 C 0.3985(5) -0.1062(5) 0.3368(4) 0.0524(14) Uani 1 1 d . . . N10 N -0.0899(4) -0.2373(4) 0.6554(3) 0.0708(15) Uani 1 1 d . . . H10A H -0.0914 -0.1729 0.6090 0.085 Uiso 1 1 calc R . . H10B H -0.1444 -0.2700 0.6548 0.085 Uiso 1 1 calc R . . C10 C 0.2865(5) -0.0695(4) 0.3693(3) 0.0478(13) Uani 1 1 d . . . O10 O 0.3032(5) -0.4979(5) 1.0058(4) 0.138(2) Uani 1 1 d . . . C11 C 0.1719(4) -0.2545(4) 0.7870(3) 0.0453(12) Uani 1 1 d . . . N11 N -0.0686(5) -0.4536(5) 0.8251(4) 0.0799(16) Uani 1 1 d . . . O11 O -0.0468(5) -0.5434(4) 0.9036(3) 0.1156(19) Uani 1 1 d . . . N12 N 0.2882(5) -0.4056(5) 0.9402(4) 0.0800(17) Uani 1 1 d . . . C12 C 0.1885(6) -0.3565(5) 0.8670(4) 0.0647(17) Uani 1 1 d . . . O12 O -0.1475(4) -0.4304(4) 0.7657(4) 0.1014(18) Uani 1 1 d . . . O13 O 0.0463(3) 0.0988(3) 0.5655(3) 0.0593(10) Uani 1 1 d U . . N13 N 0.2004(4) 0.0707(4) 0.6925(3) 0.0562(12) Uani 1 1 d . . . H13A H 0.2597 0.0539 0.7339 0.067 Uiso 1 1 calc R . . C13 C 0.1097(6) -0.4243(5) 0.8796(4) 0.0643(16) Uani 1 1 d . . . H13B H 0.1209 -0.4929 0.9336 0.077 Uiso 1 1 calc R . . O14 O 0.1813(3) -0.0372(3) 0.4931(2) 0.0592(10) Uani 1 1 d . . . N14 N 0.3660(4) -0.0866(3) 0.6018(3) 0.0493(11) Uani 1 1 d . . . H14A H 0.4220 -0.0956 0.6431 0.059 Uiso 1 1 calc R . . C14 C 0.0173(5) -0.3868(5) 0.8111(4) 0.0597(15) Uani 1 1 d . . . O15 O 0.0600(3) -0.1237(3) 0.6419(2) 0.0610(10) Uani 1 1 d . . . N15 N 0.2345(4) -0.1807(4) 0.7604(3) 0.0545(12) Uani 1 1 d . . . H15A H 0.2948 -0.1893 0.7976 0.065 Uiso 1 1 calc R . . C15 C -0.0027(5) -0.2864(5) 0.7283(4) 0.0590(15) Uani 1 1 d . . . O16 O 0.5541(5) 0.1111(5) 0.1969(3) 0.1104(18) Uani 1 1 d . . . N16 N 0.3941(5) 0.1688(6) 0.0907(4) 0.0836(18) Uani 1 1 d . . . C16 C 0.4993(12) 0.1197(12) 0.1167(11) 0.335(14) Uani 1 1 d . . . H16B H 0.5445 0.0858 0.0777 0.402 Uiso 1 1 calc R . . C17 C 0.3144(13) 0.2224(10) 0.1443(13) 0.290(10) Uani 1 1 d . . . H17A H 0.3573 0.2128 0.2025 0.435 Uiso 1 1 calc R . . H17B H 0.2515 0.1865 0.1603 0.435 Uiso 1 1 calc R . . H17C H 0.2807 0.3041 0.1062 0.435 Uiso 1 1 calc R . . C18 C 0.3205(12) 0.1870(12) 0.0116(9) 0.232(6) Uani 1 1 d . . . H18A H 0.3664 0.1534 -0.0297 0.348 Uiso 1 1 calc R . . H18B H 0.2854 0.2693 -0.0232 0.348 Uiso 1 1 calc R . . H18C H 0.2584 0.1510 0.0329 0.348 Uiso 1 1 calc R . . O17 O 0.6707(7) 0.3760(6) 0.3531(5) 0.174(3) Uani 1 1 d . . . N17 N 0.5382(6) 0.5013(6) 0.2293(5) 0.111(2) Uani 1 1 d . . . C19 C 0.6321(9) 0.4742(9) 0.2850(7) 0.141(4) Uani 1 1 d . . . H19A H 0.6737 0.5286 0.2752 0.170 Uiso 1 1 calc R . . C20 C 0.4937(10) 0.6175(7) 0.1593(7) 0.189(6) Uani 1 1 d . . . H20A H 0.5413 0.6638 0.1672 0.284 Uiso 1 1 calc R . . H20B H 0.4122 0.6507 0.1679 0.284 Uiso 1 1 calc R . . H20C H 0.4978 0.6162 0.0956 0.284 Uiso 1 1 calc R . . C21 C 0.4769(9) 0.4150(10) 0.2389(8) 0.187(5) Uani 1 1 d . . . H21A H 0.5147 0.3448 0.2933 0.280 Uiso 1 1 calc R . . H21B H 0.4805 0.3982 0.1814 0.280 Uiso 1 1 calc R . . H21C H 0.3949 0.4448 0.2483 0.280 Uiso 1 1 calc R . . O18 O 1.0357(7) 0.0753(8) 0.1357(5) 0.194(4) Uani 1 1 d . . . N18 N 0.9082(6) 0.1396(7) 0.0076(5) 0.097(2) Uani 1 1 d . . . C22 C 1.0021(12) 0.1510(11) 0.0447(10) 0.187(5) Uani 1 1 d . . . H22A H 1.0410 0.2054 0.0117 0.224 Uiso 1 1 calc R . . C23 C 0.8872(11) 0.2212(10) -0.0903(9) 0.235(7) Uani 1 1 d . . . H23A H 0.9460 0.2625 -0.1025 0.352 Uiso 1 1 calc R . . H23B H 0.8089 0.2757 -0.1012 0.352 Uiso 1 1 calc R . . H23C H 0.8928 0.1801 -0.1330 0.352 Uiso 1 1 calc R . . C24 C 0.8267(13) 0.0783(8) 0.0384(8) 0.216(7) Uani 1 1 d . . . H24A H 0.8466 0.0304 0.1058 0.324 Uiso 1 1 calc R . . H24B H 0.8287 0.0298 0.0024 0.324 Uiso 1 1 calc R . . H24C H 0.7481 0.1321 0.0285 0.324 Uiso 1 1 calc R . . OW O 0.277(2) 0.689(2) 0.3294(17) 0.385(15) Uani 0.50 1 d P . . HWB H 0.2260 0.7013 0.3682 0.462 Uiso 0.50 1 d PR . . HWA H 0.3269 0.7253 0.3305 0.462 Uiso 0.50 1 d PR . . 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 Fe 0.0406(4) 0.0515(5) 0.0377(4) -0.0165(3) -0.0052(3) -0.0161(3) N1 0.053(3) 0.065(3) 0.053(3) -0.029(3) -0.005(2) -0.019(2) C1 0.123(6) 0.044(4) 0.082(5) -0.021(4) -0.051(4) 0.006(4) O1 0.225(10) 0.173(8) 0.176(9) -0.049(7) -0.018(7) -0.026(7) N2 0.120(5) 0.069(4) 0.080(4) -0.040(3) -0.048(3) 0.001(3) O2 0.238(10) 0.181(9) 0.247(10) -0.096(8) 0.014(8) -0.039(8) C2 0.095(6) 0.090(6) 0.088(6) -0.046(5) 0.002(4) -0.025(4) C3 0.095(6) 0.080(5) 0.092(5) -0.044(4) -0.001(4) -0.018(4) O3 0.301(9) 0.112(5) 0.114(4) -0.058(4) -0.067(5) -0.081(5) N3 0.193(12) 0.135(8) 0.167(11) -0.065(8) -0.003(8) -0.018(7) O4 0.092(4) 0.132(5) 0.079(3) -0.054(3) -0.024(3) -0.033(3) N4 0.117(5) 0.105(5) 0.071(4) -0.060(4) -0.013(3) -0.044(4) C4 0.124(6) 0.065(4) 0.083(5) -0.048(4) -0.015(4) -0.028(4) O5 0.064(3) 0.097(3) 0.061(3) -0.020(3) -0.015(2) -0.023(2) N5 0.060(3) 0.054(3) 0.039(2) -0.008(2) -0.008(2) -0.025(2) C5 0.076(4) 0.049(3) 0.049(3) -0.030(3) -0.011(3) -0.028(3) O6 0.045(2) 0.078(3) 0.078(3) -0.028(2) -0.001(2) -0.007(2) C6 0.055(3) 0.044(3) 0.039(3) -0.009(2) 0.002(3) -0.027(3) N6 0.059(3) 0.099(4) 0.049(3) -0.033(3) 0.001(2) -0.017(3) O7 0.103(4) 0.185(6) 0.081(3) -0.089(4) 0.028(3) -0.043(4) C7 0.050(3) 0.066(4) 0.055(3) -0.022(3) -0.005(3) -0.031(3) N7 0.078(4) 0.143(6) 0.072(4) -0.070(4) 0.019(4) -0.042(4) N8 0.048(3) 0.060(3) 0.073(4) -0.003(3) -0.008(3) -0.025(3) O8 0.102(4) 0.219(7) 0.089(4) -0.102(4) 0.012(3) -0.055(4) C8 0.064(4) 0.086(5) 0.072(4) -0.034(4) 0.018(3) -0.040(4) N9 0.056(3) 0.055(3) 0.037(2) -0.015(2) -0.007(2) -0.027(2) O9 0.092(4) 0.103(4) 0.068(3) 0.007(3) -0.042(3) -0.043(3) C9 0.057(3) 0.055(3) 0.050(3) -0.029(3) 0.016(3) -0.013(3) N10 0.061(3) 0.076(3) 0.070(3) -0.008(3) -0.024(3) -0.037(3) C10 0.060(3) 0.055(3) 0.027(3) -0.012(2) 0.002(2) -0.021(3) O10 0.112(4) 0.123(5) 0.086(4) 0.058(3) -0.046(3) -0.027(3) C11 0.046(3) 0.051(3) 0.040(3) -0.015(3) 0.012(2) -0.018(2) N11 0.091(5) 0.080(4) 0.076(4) -0.021(3) 0.021(3) -0.047(4) O11 0.153(5) 0.101(4) 0.079(3) 0.013(3) 0.008(3) -0.080(4) N12 0.070(4) 0.089(5) 0.064(4) -0.012(3) -0.020(3) -0.020(3) C12 0.088(5) 0.056(4) 0.031(3) 0.000(3) -0.019(3) -0.014(3) O12 0.098(4) 0.108(4) 0.100(4) -0.012(3) -0.012(3) -0.068(3) O13 0.072(3) 0.058(2) 0.064(2) -0.039(2) -0.014(2) -0.0212(19) N13 0.063(3) 0.066(3) 0.048(3) -0.018(2) -0.009(2) -0.035(3) C13 0.082(4) 0.059(4) 0.047(3) -0.019(3) 0.010(3) -0.015(3) O14 0.043(2) 0.085(3) 0.059(2) -0.033(2) 0.0017(18) -0.025(2) N14 0.054(3) 0.048(3) 0.041(2) -0.009(2) -0.012(2) -0.018(2) C14 0.063(4) 0.049(3) 0.060(4) -0.009(3) -0.005(3) -0.022(3) O15 0.071(3) 0.061(2) 0.047(2) -0.0071(19) -0.0124(19) -0.031(2) N15 0.050(3) 0.075(3) 0.045(3) -0.023(2) -0.003(2) -0.029(2) C15 0.056(4) 0.071(4) 0.049(3) -0.018(3) -0.002(3) -0.025(3) O16 0.110(4) 0.127(4) 0.085(4) -0.031(3) -0.041(3) -0.031(3) N16 0.058(4) 0.116(5) 0.075(4) -0.035(4) -0.018(3) -0.025(3) C16 0.185(13) 0.295(18) 0.32(2) 0.185(16) -0.155(14) -0.168(14) C17 0.260(17) 0.148(11) 0.53(3) -0.152(16) 0.21(2) -0.136(12) C18 0.246(15) 0.267(17) 0.183(13) -0.073(12) -0.029(12) -0.092(13) O17 0.201(7) 0.123(6) 0.170(7) -0.072(5) -0.082(6) 0.018(5) N17 0.092(5) 0.094(5) 0.117(5) -0.017(4) -0.064(4) -0.009(4) C19 0.133(8) 0.156(10) 0.136(9) -0.085(8) -0.063(7) -0.001(7) C20 0.296(15) 0.081(7) 0.128(8) -0.020(6) -0.071(9) 0.017(8) C21 0.120(9) 0.234(13) 0.234(13) -0.103(11) 0.015(8) -0.076(9) O18 0.183(7) 0.269(9) 0.082(4) -0.083(5) -0.029(5) 0.031(7) N18 0.093(5) 0.110(6) 0.097(5) -0.046(4) -0.016(4) -0.036(4) C22 0.170(13) 0.204(14) 0.192(14) -0.087(12) 0.002(11) -0.046(11) C23 0.241(15) 0.171(12) 0.199(13) -0.012(10) 0.133(12) -0.001(10) C24 0.39(2) 0.113(9) 0.190(12) -0.085(8) 0.147(13) -0.101(11) OW 0.39(4) 0.44(4) 0.36(3) -0.19(3) 0.02(3) -0.13(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 Fe O14 2.007(3) . ? Fe O15 2.011(4) . ? Fe O13 2.017(4) . ? Fe N15 2.055(4) . ? Fe N13 2.065(4) . ? Fe N14 2.084(4) . ? N1 C1 1.295(7) . ? N1 O13 1.340(5) . ? N1 C5 1.360(6) . ? C1 N2 1.325(7) . ? C1 C2 1.410(9) . ? O1 N3 1.262(11) . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? O2 N3 1.269(11) . ? C2 N3 1.411(12) . ? C2 C3 1.415(8) . ? C3 C4 1.385(8) . ? C3 H3A 0.9300 . ? O3 N4 1.235(7) . ? O4 N4 1.188(6) . ? N4 C4 1.411(7) . ? C4 C5 1.436(7) . ? O5 N8 1.255(6) . ? N5 O14 1.365(5) . ? N5 C10 1.366(6) . ? N5 C6 1.373(6) . ? C5 N13 1.291(6) . ? O6 N8 1.223(6) . ? C6 N14 1.299(6) . ? C6 C7 1.376(7) . ? N6 C10 1.318(6) . ? N6 H6A 0.8600 . ? N6 H6B 0.8600 . ? O7 N7 1.263(6) . ? C7 C8 1.400(7) . ? C7 N8 1.432(6) . ? N7 O8 1.191(6) . ? N7 C9 1.448(7) . ? C8 C9 1.361(7) . ? C8 H8A 0.9300 . ? N9 C11 1.361(6) . ? N9 O15 1.362(5) . ? N9 C15 1.376(6) . ? O9 N12 1.228(6) . ? C9 C10 1.412(7) . ? N10 C15 1.338(6) . ? N10 H10A 0.8600 . ? N10 H10B 0.8600 . ? O10 N12 1.200(6) . ? C11 N15 1.308(6) . ? C11 C12 1.381(7) . ? N11 O12 1.185(6) . ? N11 O11 1.276(6) . ? N11 C14 1.465(7) . ? N12 C12 1.439(6) . ? C12 C13 1.407(8) . ? N13 H13A 0.8600 . ? C13 C14 1.351(7) . ? C13 H13B 0.9300 . ? N14 H14A 0.8600 . ? C14 C15 1.388(7) . ? N15 H15A 0.8600 . ? O16 C16 1.321(15) . ? N16 C16 1.210(12) . ? N16 C18 1.380(11) . ? N16 C17 1.423(14) . ? C16 H16B 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O17 C19 1.261(10) . ? N17 C19 1.273(8) . ? N17 C20 1.428(9) . ? N17 C21 1.450(10) . ? C19 H19A 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? O18 C22 1.335(13) . ? N18 C22 1.305(13) . ? N18 C24 1.376(12) . ? N18 C23 1.431(11) . ? C22 H22A 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? OW HWB 0.8499 . ? OW HWA 0.8500 . ? 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 O14 Fe O15 84.00(14) . . ? O14 Fe O13 79.08(15) . . ? O15 Fe O13 81.46(15) . . ? O14 Fe N15 132.35(16) . . ? O15 Fe N15 75.14(15) . . ? O13 Fe N15 136.84(17) . . ? O14 Fe N13 134.91(16) . . ? O15 Fe N13 126.92(17) . . ? O13 Fe N13 75.22(16) . . ? N15 Fe N13 90.55(16) . . ? O14 Fe N14 75.48(15) . . ? O15 Fe N14 133.39(16) . . ? O13 Fe N14 132.71(16) . . ? N15 Fe N14 88.51(16) . . ? N13 Fe N14 95.89(17) . . ? C1 N1 O13 113.7(4) . . ? C1 N1 C5 129.6(5) . . ? O13 N1 C5 116.4(4) . . ? N1 C1 N2 119.9(6) . . ? N1 C1 C2 115.4(6) . . ? N2 C1 C2 123.9(6) . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C1 C2 N3 123.2(8) . . ? C1 C2 C3 121.7(7) . . ? N3 C2 C3 115.1(8) . . ? C4 C3 C2 117.8(7) . . ? C4 C3 H3A 121.1 . . ? C2 C3 H3A 121.1 . . ? O1 N3 O2 118.7(13) . . ? O1 N3 C2 121.1(12) . . ? O2 N3 C2 120.2(12) . . ? O4 N4 O3 120.9(6) . . ? O4 N4 C4 121.1(6) . . ? O3 N4 C4 117.9(7) . . ? C3 C4 N4 118.7(6) . . ? C3 C4 C5 120.5(6) . . ? N4 C4 C5 120.6(6) . . ? O14 N5 C10 116.0(4) . . ? O14 N5 C6 118.0(4) . . ? C10 N5 C6 125.9(5) . . ? N13 C5 N1 114.3(4) . . ? N13 C5 C4 130.2(5) . . ? N1 C5 C4 114.6(5) . . ? N14 C6 N5 112.3(5) . . ? N14 C6 C7 131.6(5) . . ? N5 C6 C7 116.1(5) . . ? C10 N6 H6A 120.0 . . ? C10 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? C6 C7 C8 121.2(5) . . ? C6 C7 N8 124.7(5) . . ? C8 C7 N8 114.2(5) . . ? O8 N7 O7 124.4(6) . . ? O8 N7 C9 118.9(6) . . ? O7 N7 C9 116.7(6) . . ? O6 N8 O5 120.2(5) . . ? O6 N8 C7 124.1(6) . . ? O5 N8 C7 115.6(5) . . ? C9 C8 C7 120.0(6) . . ? C9 C8 H8A 120.0 . . ? C7 C8 H8A 120.0 . . ? C11 N9 O15 117.4(4) . . ? C11 N9 C15 125.1(4) . . ? O15 N9 C15 117.3(4) . . ? C8 C9 C10 120.7(5) . . ? C8 C9 N7 119.2(5) . . ? C10 C9 N7 120.0(5) . . ? C15 N10 H10A 120.0 . . ? C15 N10 H10B 120.0 . . ? H10A N10 H10B 120.0 . . ? N6 C10 N5 115.5(5) . . ? N6 C10 C9 128.6(5) . . ? N5 C10 C9 115.9(5) . . ? N15 C11 N9 112.0(4) . . ? N15 C11 C12 131.0(5) . . ? N9 C11 C12 116.9(5) . . ? O12 N11 O11 122.5(6) . . ? O12 N11 C14 122.7(6) . . ? O11 N11 C14 114.7(6) . . ? O10 N12 O9 121.6(6) . . ? O10 N12 C12 122.3(6) . . ? O9 N12 C12 115.4(6) . . ? C11 C12 C13 121.1(5) . . ? C11 C12 N12 124.2(6) . . ? C13 C12 N12 114.6(5) . . ? N1 O13 Fe 116.2(3) . . ? C5 N13 Fe 117.5(3) . . ? C5 N13 H13A 121.2 . . ? Fe N13 H13A 121.2 . . ? C14 C13 C12 118.0(6) . . ? C14 C13 H13B 121.0 . . ? C12 C13 H13B 121.0 . . ? N5 O14 Fe 115.4(3) . . ? C6 N14 Fe 118.4(3) . . ? C6 N14 H14A 120.8 . . ? Fe N14 H14A 120.8 . . ? C13 C14 C15 123.6(6) . . ? C13 C14 N11 118.7(6) . . ? C15 C14 N11 117.7(5) . . ? N9 O15 Fe 115.6(3) . . ? C11 N15 Fe 119.4(3) . . ? C11 N15 H15A 120.3 . . ? Fe N15 H15A 120.3 . . ? N10 C15 N9 114.1(5) . . ? N10 C15 C14 130.7(5) . . ? N9 C15 C14 115.2(5) . . ? C16 N16 C18 133.5(13) . . ? C16 N16 C17 123.6(12) . . ? C18 N16 C17 102.9(9) . . ? N16 C16 O16 124.3(19) . . ? N16 C16 H16B 117.9 . . ? O16 C16 H16B 117.9 . . ? N16 C17 H17A 109.5 . . ? N16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N16 C18 H18A 109.5 . . ? N16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C19 N17 C20 119.0(9) . . ? C19 N17 C21 119.8(9) . . ? C20 N17 C21 121.2(7) . . ? O17 C19 N17 122.1(11) . . ? O17 C19 H19A 119.0 . . ? N17 C19 H19A 119.0 . . ? N17 C20 H20A 109.5 . . ? N17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N17 C21 H21A 109.5 . . ? N17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C22 N18 C24 137.7(11) . . ? C22 N18 C23 105.5(10) . . ? C24 N18 C23 116.7(9) . . ? N18 C22 O18 112.1(13) . . ? N18 C22 H22A 124.0 . . ? O18 C22 H22A 124.0 . . ? N18 C23 H23A 109.5 . . ? N18 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N18 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N18 C24 H24A 109.5 . . ? N18 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N18 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? HWB OW HWA 107.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O13 N1 C1 N2 17.4(10) . . . . ? C5 N1 C1 N2 -169.4(6) . . . . ? O13 N1 C1 C2 -172.5(6) . . . . ? C5 N1 C1 C2 0.7(12) . . . . ? N1 C1 C2 N3 177.4(9) . . . . ? N2 C1 C2 N3 -13.0(14) . . . . ? N1 C1 C2 C3 -2.9(12) . . . . ? N2 C1 C2 C3 166.7(7) . . . . ? C1 C2 C3 C4 0.2(12) . . . . ? N3 C2 C3 C4 179.9(8) . . . . ? C1 C2 N3 O1 -1.4(18) . . . . ? C3 C2 N3 O1 178.9(11) . . . . ? C1 C2 N3 O2 -178.8(11) . . . . ? C3 C2 N3 O2 1.5(16) . . . . ? C2 C3 C4 N4 -179.5(7) . . . . ? C2 C3 C4 C5 4.6(11) . . . . ? O4 N4 C4 C3 -179.1(7) . . . . ? O3 N4 C4 C3 3.3(11) . . . . ? O4 N4 C4 C5 -3.3(11) . . . . ? O3 N4 C4 C5 179.1(7) . . . . ? C1 N1 C5 N13 -166.6(6) . . . . ? O13 N1 C5 N13 6.5(7) . . . . ? C1 N1 C5 C4 3.9(10) . . . . ? O13 N1 C5 C4 177.0(5) . . . . ? C3 C4 C5 N13 162.1(7) . . . . ? N4 C4 C5 N13 -13.6(11) . . . . ? C3 C4 C5 N1 -6.5(10) . . . . ? N4 C4 C5 N1 177.7(6) . . . . ? O14 N5 C6 N14 -0.3(6) . . . . ? C10 N5 C6 N14 175.3(5) . . . . ? O14 N5 C6 C7 179.5(4) . . . . ? C10 N5 C6 C7 -4.9(7) . . . . ? N14 C6 C7 C8 -178.6(5) . . . . ? N5 C6 C7 C8 1.7(8) . . . . ? N14 C6 C7 N8 1.7(9) . . . . ? N5 C6 C7 N8 -178.0(5) . . . . ? C6 C7 N8 O6 179.3(5) . . . . ? C8 C7 N8 O6 -0.4(8) . . . . ? C6 C7 N8 O5 -3.0(8) . . . . ? C8 C7 N8 O5 177.3(5) . . . . ? C6 C7 C8 C9 1.4(9) . . . . ? N8 C7 C8 C9 -178.9(5) . . . . ? C7 C8 C9 C10 -1.7(9) . . . . ? C7 C8 C9 N7 -178.0(5) . . . . ? O8 N7 C9 C8 -175.0(6) . . . . ? O7 N7 C9 C8 2.6(9) . . . . ? O8 N7 C9 C10 8.6(10) . . . . ? O7 N7 C9 C10 -173.8(6) . . . . ? O14 N5 C10 N6 -0.4(7) . . . . ? C6 N5 C10 N6 -176.0(5) . . . . ? O14 N5 C10 C9 -179.7(4) . . . . ? C6 N5 C10 C9 4.7(7) . . . . ? C8 C9 C10 N6 179.7(6) . . . . ? N7 C9 C10 N6 -4.0(9) . . . . ? C8 C9 C10 N5 -1.1(8) . . . . ? N7 C9 C10 N5 175.2(5) . . . . ? O15 N9 C11 N15 -4.0(6) . . . . ? C15 N9 C11 N15 180.0(5) . . . . ? O15 N9 C11 C12 178.9(5) . . . . ? C15 N9 C11 C12 2.8(8) . . . . ? N15 C11 C12 C13 -178.5(5) . . . . ? N9 C11 C12 C13 -2.0(8) . . . . ? N15 C11 C12 N12 -2.1(10) . . . . ? N9 C11 C12 N12 174.4(5) . . . . ? O10 N12 C12 C11 -175.7(7) . . . . ? O9 N12 C12 C11 13.8(9) . . . . ? O10 N12 C12 C13 1.0(10) . . . . ? O9 N12 C12 C13 -169.5(6) . . . . ? C1 N1 O13 Fe 170.4(5) . . . . ? C5 N1 O13 Fe -3.7(6) . . . . ? O14 Fe O13 N1 -142.3(4) . . . . ? O15 Fe O13 N1 132.2(4) . . . . ? N15 Fe O13 N1 74.8(4) . . . . ? N13 Fe O13 N1 0.3(3) . . . . ? N14 Fe O13 N1 -84.0(4) . . . . ? N1 C5 N13 Fe -6.3(6) . . . . ? C4 C5 N13 Fe -175.0(6) . . . . ? O14 Fe N13 C5 60.7(5) . . . . ? O15 Fe N13 C5 -63.7(5) . . . . ? O13 Fe N13 C5 3.4(4) . . . . ? N15 Fe N13 C5 -135.4(4) . . . . ? N14 Fe N13 C5 136.0(4) . . . . ? C11 C12 C13 C14 0.2(9) . . . . ? N12 C12 C13 C14 -176.6(5) . . . . ? C10 N5 O14 Fe 179.3(3) . . . . ? C6 N5 O14 Fe -4.8(5) . . . . ? O15 Fe O14 N5 -132.4(3) . . . . ? O13 Fe O14 N5 145.2(3) . . . . ? N15 Fe O14 N5 -68.8(4) . . . . ? N13 Fe O14 N5 89.2(4) . . . . ? N14 Fe O14 N5 5.4(3) . . . . ? N5 C6 N14 Fe 5.1(5) . . . . ? C7 C6 N14 Fe -174.6(5) . . . . ? O14 Fe N14 C6 -6.0(4) . . . . ? O15 Fe N14 C6 60.9(4) . . . . ? O13 Fe N14 C6 -65.6(4) . . . . ? N15 Fe N14 C6 128.7(4) . . . . ? N13 Fe N14 C6 -140.9(4) . . . . ? C12 C13 C14 C15 1.1(9) . . . . ? C12 C13 C14 N11 -177.4(5) . . . . ? O12 N11 C14 C13 -175.3(6) . . . . ? O11 N11 C14 C13 0.2(9) . . . . ? O12 N11 C14 C15 6.1(10) . . . . ? O11 N11 C14 C15 -178.4(6) . . . . ? C11 N9 O15 Fe 7.8(5) . . . . ? C15 N9 O15 Fe -175.9(4) . . . . ? O14 Fe O15 N9 130.6(3) . . . . ? O13 Fe O15 N9 -149.6(3) . . . . ? N15 Fe O15 N9 -6.2(3) . . . . ? N13 Fe O15 N9 -85.4(4) . . . . ? N14 Fe O15 N9 67.1(4) . . . . ? N9 C11 N15 Fe -1.6(6) . . . . ? C12 C11 N15 Fe 175.1(5) . . . . ? O14 Fe N15 C11 -62.8(5) . . . . ? O15 Fe N15 C11 4.3(4) . . . . ? O13 Fe N15 C11 63.8(5) . . . . ? N13 Fe N15 C11 132.6(4) . . . . ? N14 Fe N15 C11 -131.5(4) . . . . ? C11 N9 C15 N10 177.0(5) . . . . ? O15 N9 C15 N10 1.0(7) . . . . ? C11 N9 C15 C14 -1.6(8) . . . . ? O15 N9 C15 C14 -177.7(5) . . . . ? C13 C14 C15 N10 -178.8(6) . . . . ? N11 C14 C15 N10 -0.3(10) . . . . ? C13 C14 C15 N9 -0.5(9) . . . . ? N11 C14 C15 N9 178.1(5) . . . . ? C18 N16 C16 O16 -179.6(10) . . . . ? C17 N16 C16 O16 -1.2(16) . . . . ? C20 N17 C19 O17 174.4(9) . . . . ? C21 N17 C19 O17 -4.4(16) . . . . ? C24 N18 C22 O18 7.6(19) . . . . ? C23 N18 C22 O18 -177.1(9) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.404 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.067