# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H24 Cl0.54 Mn4 N30.38 O4' _chemical_formula_weight 1281.19 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 22.368(10) _cell_length_b 15.690(7) _cell_length_c 14.069(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.503(7) _cell_angle_gamma 90.00 _cell_volume 4937(4) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 7358 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 26.1 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.724 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2567 _exptl_absorpt_coefficient_mu 1.109 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.756 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% none _diffrn_reflns_number 20874 _diffrn_reflns_av_R_equivalents 0.0850 _diffrn_reflns_av_sigmaI/netI 0.0721 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4081 _reflns_number_gt 3772 _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^)+(0.0980P)^2^+151.1413P] 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 SHELXL _refine_ls_extinction_coef 0.0020(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4081 _refine_ls_number_parameters 390 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1272 _refine_ls_R_factor_gt 0.1204 _refine_ls_wR_factor_ref 0.2903 _refine_ls_wR_factor_gt 0.2856 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _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 Mn1 Mn 0.80534(6) 0.32487(9) -0.00921(11) 0.0236(5) Uani 1 1 d . . . Mn2 Mn 0.80811(6) 0.18476(9) 0.17979(11) 0.0256(5) Uani 1 1 d . . . N7 N 0.7101(3) 0.1802(6) 0.1619(6) 0.030(2) Uani 1 1 d . . . N4 N 0.7975(4) 0.1806(5) 0.0109(7) 0.034(2) Uani 1 1 d . . . N13 N 0.8150(3) 0.4727(5) 0.0013(6) 0.0248(17) Uani 1 1 d . . . N16 N 0.8088(4) 0.0342(5) 0.1830(6) 0.0273(18) Uani 1 1 d . A . N8 N 0.6744(4) 0.1636(5) 0.2209(6) 0.0279(19) Uani 1 1 d . . . C19 C 0.8692(4) 0.4942(7) -0.0328(7) 0.028(2) Uani 1 1 d . . . N14 N 0.9050(3) 0.3455(5) -0.0557(6) 0.0264(18) Uani 1 1 d . . . C21 C 0.8014(4) 0.6257(7) 0.0174(8) 0.032(2) Uani 1 1 d . . . H21A H 0.7772 0.6706 0.0366 0.039 Uiso 1 1 d R . . N2 N 0.8504(4) 0.3705(6) 0.1863(6) 0.035(2) Uani 1 1 d . . . N15 N 0.9065(4) 0.1527(6) 0.1514(7) 0.034(2) Uani 1 1 d . A . C23 C 0.8914(4) 0.5743(7) -0.0476(7) 0.028(2) Uani 1 1 d . . . C34 C 0.8637(5) 0.0093(7) 0.1666(8) 0.034(2) Uani 1 1 d . . . N5 N 0.8267(4) 0.1307(7) -0.0374(7) 0.039(2) Uani 1 1 d . . . C16 C 1.0095(5) 0.4212(8) -0.1342(7) 0.037(3) Uani 1 1 d . . . H16A H 1.0434 0.4461 -0.1600 0.044 Uiso 1 1 d R . . C20 C 0.7821(4) 0.5407(7) 0.0261(8) 0.032(2) Uani 1 1 d . . . H20A H 0.7442 0.5311 0.0508 0.038 Uiso 1 1 d R . . N3 N 0.8733(4) 0.4256(6) 0.2288(7) 0.043(2) Uani 1 1 d . A . N1 N 0.8258(4) 0.3172(6) 0.1425(7) 0.035(2) Uani 1 1 d . A . C33 C 0.7701(5) -0.0307(9) 0.1978(9) 0.048(3) Uani 1 1 d . . . H33A H 0.7309 -0.0165 0.2126 0.058 Uiso 1 1 d R A . N9 N 0.6388(4) 0.1474(7) 0.2805(7) 0.039(2) Uani 1 1 d . A . C35 C 0.9134(4) 0.0686(6) 0.1503(8) 0.027(2) Uani 1 1 d . A . C15 C 1.0031(4) 0.3340(7) -0.1274(7) 0.031(2) Uani 1 1 d . . . H15A H 1.0340 0.2988 -0.1475 0.037 Uiso 1 1 d R . . C17 C 0.9618(4) 0.4703(7) -0.0999(7) 0.033(2) Uani 1 1 d . . . C18 C 0.9124(4) 0.4291(6) -0.0642(7) 0.026(2) Uani 1 1 d . . . C22 C 0.8562(5) 0.6407(7) -0.0203(8) 0.032(2) Uani 1 1 d . . . H22A H 0.8698 0.6964 -0.0273 0.038 Uiso 1 1 d R . . C28 C 0.9645(5) 0.0234(7) 0.1331(10) 0.047(3) Uani 1 1 d . . . C25 C 0.9578(5) 0.1943(7) 0.1359(9) 0.040(3) Uani 1 1 d . . . H25A H 0.9568 0.2535 0.1367 0.048 Uiso 1 1 d R A . N6 N 0.8562(5) 0.0874(7) -0.0783(10) 0.059(3) Uani 1 1 d . A . C26 C 1.0125(5) 0.1553(8) 0.1195(10) 0.047(3) Uani 1 1 d . A . H26A H 1.0461 0.1892 0.1102 0.057 Uiso 1 1 d R . . C14 C 0.9501(5) 0.2967(7) -0.0900(7) 0.031(2) Uani 1 1 d . . . H14A H 0.9462 0.2376 -0.0894 0.038 Uiso 1 1 d R . . C27 C 1.0185(6) 0.0659(9) 0.1157(10) 0.055(4) Uani 1 1 d . A . H27A H 1.0544 0.0382 0.1034 0.066 Uiso 1 1 d R . . C29 C 0.9489(6) -0.0737(7) 0.1417(11) 0.051(3) Uani 1 1 d . A . O1 O 0.9864(3) 0.6218(5) -0.1129(6) 0.0420(19) Uani 1 1 d . . . C31 C 0.8424(6) -0.1384(8) 0.1758(11) 0.051(3) Uani 1 1 d . . . H31A H 0.8535 -0.1955 0.1737 0.061 Uiso 1 1 d R A . C24 C 0.9522(4) 0.5620(8) -0.0927(7) 0.035(2) Uani 1 1 d . . . C32 C 0.7837(6) -0.1139(8) 0.1925(10) 0.051(3) Uani 1 1 d . A . H32A H 0.7541 -0.1549 0.2000 0.061 Uiso 1 1 d R . . O2 O 0.9837(5) -0.1301(7) 0.1318(12) 0.100(5) Uani 1 1 d . . . C30 C 0.8844(5) -0.0727(7) 0.1621(10) 0.045(3) Uani 1 1 d . A . N10 N 0.8087(13) 0.201(2) 0.327(2) 0.036(7) Uani 0.73(4) 1 d P A 1 N12 N 0.8543(7) 0.1296(11) 0.4567(12) 0.055(6) Uani 0.73(4) 1 d P A 1 N11 N 0.8307(10) 0.1661(15) 0.387(3) 0.029(6) Uani 0.73(4) 1 d P A 1 Cl1 Cl 0.8241(10) 0.1852(15) 0.3504(14) 0.030(8) Uani 0.27(4) 1 d P A 2 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 Mn1 0.0172(8) 0.0207(8) 0.0331(9) 0.0006(6) 0.0024(6) -0.0014(5) Mn2 0.0184(8) 0.0218(8) 0.0366(9) 0.0013(6) 0.0034(6) -0.0009(6) N7 0.011(4) 0.045(5) 0.036(5) 0.000(4) 0.010(3) -0.001(3) N4 0.042(5) 0.022(4) 0.037(5) -0.001(4) 0.005(4) 0.009(4) N13 0.020(4) 0.017(4) 0.037(5) 0.001(3) 0.005(3) -0.006(3) N16 0.025(4) 0.024(4) 0.032(4) 0.004(3) 0.000(3) 0.004(3) N8 0.022(4) 0.019(4) 0.042(5) -0.003(4) -0.006(4) 0.007(3) C19 0.016(4) 0.032(5) 0.035(5) 0.003(4) 0.001(4) -0.004(4) N14 0.019(4) 0.022(4) 0.038(5) -0.003(3) 0.009(3) 0.007(3) C21 0.018(5) 0.028(5) 0.050(7) -0.002(5) -0.002(4) 0.010(4) N2 0.036(5) 0.036(5) 0.031(5) 0.006(4) 0.008(4) 0.003(4) N15 0.024(4) 0.034(5) 0.044(5) 0.004(4) 0.001(4) -0.006(4) C23 0.026(5) 0.032(5) 0.026(5) 0.000(4) 0.002(4) -0.003(4) C34 0.032(5) 0.028(5) 0.041(6) 0.003(5) 0.001(4) 0.001(4) N5 0.028(5) 0.047(6) 0.044(5) 0.008(5) 0.006(4) -0.004(5) C16 0.028(5) 0.057(7) 0.026(5) 0.001(5) 0.009(4) -0.003(5) C20 0.016(4) 0.031(5) 0.048(6) 0.007(5) 0.014(4) 0.002(4) N3 0.042(5) 0.039(6) 0.048(6) -0.016(5) -0.005(4) 0.010(5) N1 0.037(5) 0.028(5) 0.038(5) -0.005(4) 0.000(4) -0.010(4) C33 0.033(6) 0.056(8) 0.056(8) 0.002(6) 0.006(5) -0.012(6) N9 0.017(4) 0.065(7) 0.035(5) 0.005(5) 0.002(4) -0.009(4) C35 0.021(5) 0.011(4) 0.050(6) 0.007(4) 0.002(4) -0.003(4) C15 0.012(4) 0.043(6) 0.037(6) -0.003(5) -0.010(4) 0.008(4) C17 0.023(5) 0.047(6) 0.029(5) -0.001(5) 0.005(4) -0.002(4) C18 0.017(4) 0.030(5) 0.032(5) 0.001(4) 0.007(4) -0.002(4) C22 0.029(5) 0.023(5) 0.043(6) 0.000(4) 0.009(4) -0.005(4) C28 0.028(6) 0.028(6) 0.084(9) 0.020(6) 0.014(6) 0.010(5) C25 0.033(6) 0.032(6) 0.055(7) 0.013(5) -0.007(5) -0.002(5) N6 0.053(7) 0.043(6) 0.083(9) -0.015(6) 0.021(6) 0.017(5) C26 0.027(6) 0.040(7) 0.075(9) 0.019(6) 0.006(6) -0.001(5) C14 0.027(5) 0.034(5) 0.034(6) 0.002(4) -0.004(4) 0.006(4) C27 0.038(7) 0.060(8) 0.067(9) 0.015(7) 0.016(6) 0.026(6) C29 0.050(7) 0.024(6) 0.078(10) 0.007(6) 0.008(7) 0.018(5) O1 0.038(4) 0.040(5) 0.047(5) 0.008(4) 0.001(4) -0.014(4) C31 0.049(7) 0.021(5) 0.083(10) 0.000(6) 0.001(7) 0.001(5) C24 0.024(5) 0.051(7) 0.030(5) 0.001(5) -0.002(4) -0.014(5) C32 0.058(8) 0.031(6) 0.064(8) 0.012(6) 0.002(6) -0.007(6) O2 0.067(7) 0.043(6) 0.190(15) 0.038(8) 0.046(8) 0.026(5) C30 0.037(6) 0.032(6) 0.067(8) 0.004(6) 0.012(6) 0.006(5) N10 0.037(14) 0.042(12) 0.030(16) -0.016(10) -0.013(9) -0.001(10) N12 0.050(10) 0.071(12) 0.044(10) 0.020(8) 0.000(7) 0.005(8) N11 0.014(8) 0.025(10) 0.049(16) -0.021(11) 0.006(12) -0.002(7) Cl1 0.022(11) 0.052(15) 0.017(15) 0.003(10) -0.010(10) -0.013(10) _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 Mn1 N7 2.174(9) 7_655 ? Mn1 N1 2.182(10) . ? Mn1 N4 2.288(8) . ? Mn1 N4 2.302(10) 7_655 ? Mn1 N13 2.333(8) . ? Mn1 N14 2.352(8) . ? Mn2 N10 2.09(3) . ? Mn2 N1 2.180(9) . ? Mn2 N7 2.205(8) . ? Mn2 N15 2.296(9) . ? Mn2 N16 2.363(8) . ? Mn2 N4 2.387(9) . ? Mn2 Cl1 2.424(19) . ? N7 N8 1.186(12) . ? N7 Mn1 2.174(9) 7_655 ? N4 N5 1.228(13) . ? N4 Mn1 2.302(10) 7_655 ? N13 C20 1.345(12) . ? N13 C19 1.352(12) . ? N16 C34 1.310(13) . ? N16 C33 1.355(14) . ? N8 N9 1.188(12) . ? C19 C23 1.367(14) . ? C19 C18 1.475(14) . ? N14 C18 1.327(13) . ? N14 C14 1.358(13) . ? C21 C22 1.361(14) . ? C21 C20 1.408(14) . ? N2 N3 1.167(14) . ? N2 N1 1.173(13) . ? N15 C35 1.328(13) . ? N15 C25 1.340(14) . ? C23 C22 1.363(14) . ? C23 C24 1.518(14) . ? C34 C30 1.369(16) . ? C34 C35 1.469(14) . ? N5 N6 1.112(14) . ? C16 C15 1.380(16) . ? C16 C17 1.405(15) . ? C33 C32 1.341(18) . ? C35 C28 1.369(14) . ? C15 C14 1.428(15) . ? C17 C18 1.380(14) . ? C17 C24 1.458(16) . ? C28 C27 1.402(17) . ? C28 C29 1.569(16) . ? C25 C26 1.390(17) . ? C26 C27 1.410(19) . ? C29 O2 1.189(15) . ? C29 C30 1.474(17) . ? O1 C24 1.245(13) . ? C31 C32 1.390(19) . ? C31 C30 1.408(17) . ? N10 N11 1.12(5) . ? N12 N11 1.25(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N7 Mn1 N1 173.9(3) 7_655 . ? N7 Mn1 N4 94.3(3) 7_655 . ? N1 Mn1 N4 80.8(3) . . ? N7 Mn1 N4 80.7(3) 7_655 7_655 ? N1 Mn1 N4 102.1(3) . 7_655 ? N4 Mn1 N4 83.5(3) . 7_655 ? N7 Mn1 N13 96.5(3) 7_655 . ? N1 Mn1 N13 88.5(3) . . ? N4 Mn1 N13 169.2(3) . . ? N4 Mn1 N13 97.4(3) 7_655 . ? N7 Mn1 N14 82.7(3) 7_655 . ? N1 Mn1 N14 95.0(3) . . ? N4 Mn1 N14 104.1(3) . . ? N4 Mn1 N14 162.2(3) 7_655 . ? N13 Mn1 N14 78.1(3) . . ? N10 Mn2 N1 97.2(9) . . ? N10 Mn2 N7 96.6(9) . . ? N1 Mn2 N7 100.7(3) . . ? N10 Mn2 N15 101.6(8) . . ? N1 Mn2 N15 89.5(3) . . ? N7 Mn2 N15 157.9(3) . . ? N10 Mn2 N16 95.8(9) . . ? N1 Mn2 N16 163.0(3) . . ? N7 Mn2 N16 88.6(3) . . ? N15 Mn2 N16 77.1(3) . . ? N10 Mn2 N4 172.5(8) . . ? N1 Mn2 N4 78.6(3) . . ? N7 Mn2 N4 78.2(3) . . ? N15 Mn2 N4 84.7(3) . . ? N16 Mn2 N4 89.6(3) . . ? N10 Mn2 Cl1 10.5(11) . . ? N1 Mn2 Cl1 102.1(6) . . ? N7 Mn2 Cl1 104.5(6) . . ? N15 Mn2 Cl1 92.3(6) . . ? N16 Mn2 Cl1 89.0(6) . . ? N4 Mn2 Cl1 176.9(6) . . ? N8 N7 Mn1 125.5(7) . 7_655 ? N8 N7 Mn2 127.0(7) . . ? Mn1 N7 Mn2 105.3(3) 7_655 . ? N5 N4 Mn1 121.5(7) . . ? N5 N4 Mn1 120.4(7) . 7_655 ? Mn1 N4 Mn1 96.5(3) . 7_655 ? N5 N4 Mn2 121.3(7) . . ? Mn1 N4 Mn2 95.1(3) . . ? Mn1 N4 Mn2 95.8(3) 7_655 . ? C20 N13 C19 112.8(8) . . ? C20 N13 Mn1 139.1(6) . . ? C19 N13 Mn1 108.0(6) . . ? C34 N16 C33 113.8(9) . . ? C34 N16 Mn2 107.5(7) . . ? C33 N16 Mn2 138.7(8) . . ? N7 N8 N9 179.4(12) . . ? N13 C19 C23 127.7(9) . . ? N13 C19 C18 121.6(9) . . ? C23 C19 C18 110.6(8) . . ? C18 N14 C14 115.7(8) . . ? C18 N14 Mn1 106.2(6) . . ? C14 N14 Mn1 136.8(7) . . ? C22 C21 C20 118.4(9) . . ? N3 N2 N1 177.5(12) . . ? C35 N15 C25 112.4(9) . . ? C35 N15 Mn2 109.4(6) . . ? C25 N15 Mn2 138.2(8) . . ? C22 C23 C19 116.7(9) . . ? C22 C23 C24 137.4(10) . . ? C19 C23 C24 106.0(9) . . ? N16 C34 C30 127.3(10) . . ? N16 C34 C35 123.3(9) . . ? C30 C34 C35 109.4(9) . . ? N6 N5 N4 175.6(13) . . ? C15 C16 C17 116.1(10) . . ? N13 C20 C21 124.1(8) . . ? N2 N1 Mn2 129.7(8) . . ? N2 N1 Mn1 124.6(8) . . ? Mn2 N1 Mn1 104.6(4) . . ? C32 C33 N16 125.2(12) . . ? N15 C35 C28 127.9(9) . . ? N15 C35 C34 122.6(9) . . ? C28 C35 C34 109.5(9) . . ? C16 C15 C14 121.3(9) . . ? C18 C17 C16 118.8(10) . . ? C18 C17 C24 108.6(9) . . ? C16 C17 C24 132.6(10) . . ? N14 C18 C17 126.6(9) . . ? N14 C18 C19 125.1(8) . . ? C17 C18 C19 108.2(9) . . ? C21 C22 C23 120.1(10) . . ? C35 C28 C27 120.5(10) . . ? C35 C28 C29 107.5(9) . . ? C27 C28 C29 131.9(10) . . ? N15 C25 C26 124.7(11) . . ? C25 C26 C27 121.9(11) . . ? N14 C14 C15 121.4(10) . . ? C28 C27 C26 112.6(10) . . ? O2 C29 C30 132.4(13) . . ? O2 C29 C28 124.6(12) . . ? C30 C29 C28 103.0(9) . . ? C32 C31 C30 116.9(11) . . ? O1 C24 C17 129.5(10) . . ? O1 C24 C23 123.7(11) . . ? C17 C24 C23 106.7(9) . . ? C33 C32 C31 119.6(12) . . ? C34 C30 C31 117.1(10) . . ? C34 C30 C29 110.5(10) . . ? C31 C30 C29 132.4(11) . . ? N11 N10 Mn2 134(3) . . ? N10 N11 N12 178(3) . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 1.848 _refine_diff_density_min -0.700 _refine_diff_density_rms 0.164 _database_code_depnum_ccdc_archive 'CCDC 927367' ####################################################################### # # 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 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H24 Co4 N32 O4' _chemical_formula_weight 1300.67 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 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 22.553(5) _cell_length_b 15.665(3) _cell_length_c 14.048(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.12(3) _cell_angle_gamma 90.00 _cell_volume 4962.9(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22575 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.741 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2608 _exptl_absorpt_coefficient_mu 1.396 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% none _diffrn_reflns_number 20478 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4248 _reflns_number_gt 3828 _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^)+(0.0301P)^2^+126.0132P] 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_number_reflns 4248 _refine_ls_number_parameters 411 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1027 _refine_ls_R_factor_gt 0.0953 _refine_ls_wR_factor_ref 0.2051 _refine_ls_wR_factor_gt 0.2019 _refine_ls_goodness_of_fit_ref 1.225 _refine_ls_restrained_S_all 1.225 _refine_ls_shift/su_max 0.015 _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 0.30286(5) 0.17602(7) 0.51239(8) 0.0281(3) Uani 1 1 d . . . Co2 Co 0.19365(5) 0.18952(7) 0.67116(8) 0.0289(3) Uani 1 1 d . . . N1 N 0.2873(3) 0.1895(5) 0.6580(5) 0.0330(16) Uani 1 1 d . . . N4 N 0.2048(3) 0.1836(4) 0.5110(5) 0.0354(17) Uani 1 1 d . . . N15 N 0.1943(3) 0.0438(4) 0.6867(6) 0.0348(17) Uani 1 1 d . . . N11 N 0.1692(3) 0.1699(5) 0.8745(6) 0.0383(18) Uani 1 1 d . . . N14 N 0.3114(3) 0.0348(5) 0.5075(5) 0.0336(17) Uani 1 1 d . . . N7 N 0.3175(4) 0.1803(5) 0.3677(6) 0.0411(19) Uani 1 1 d . . . N16 N 0.0983(3) 0.1610(5) 0.6525(6) 0.0384(18) Uani 1 1 d . . . N8 N 0.3476(4) 0.1284(5) 0.3241(6) 0.0403(19) Uani 1 1 d . . . N13 N 0.4010(3) 0.1619(5) 0.5571(6) 0.0380(18) Uani 1 1 d . . . N2 N 0.3217(3) 0.1677(5) 0.7192(6) 0.0399(18) Uani 1 1 d . . . N5 N 0.1736(4) 0.1352(5) 0.4627(6) 0.047(2) Uani 1 1 d . . . O1 O 0.4844(4) -0.1150(5) 0.6152(6) 0.066(2) Uani 1 1 d . . . C11 C 0.4099(4) 0.0772(6) 0.5676(6) 0.0338(19) Uani 1 1 d . . . C6 C 0.3878(4) -0.0680(6) 0.5522(7) 0.037(2) Uani 1 1 d . . . C2 C 0.5004(4) 0.1745(7) 0.6257(8) 0.047(2) Uani 1 1 d . . . N10 N 0.1933(4) 0.2119(6) 0.8137(6) 0.051(2) Uani 1 1 d . . . C10 C 0.3660(4) 0.0137(5) 0.5393(6) 0.0317(19) Uani 1 1 d . . . C4 C 0.4604(4) 0.0364(6) 0.6012(7) 0.040(2) Uani 1 1 d . . . C7 C 0.3530(5) -0.1353(6) 0.5242(8) 0.042(2) Uani 1 1 d . . . C12 C 0.2331(5) -0.0197(7) 0.7025(8) 0.053(3) Uani 1 1 d . . . H12A H 0.2721 -0.0054 0.7167 0.063 Uiso 1 1 calc R . . C22 C 0.1392(4) 0.0171(5) 0.6699(6) 0.0332(19) Uani 1 1 d . . . C9 C 0.2779(4) -0.0325(6) 0.4808(8) 0.042(2) Uani 1 1 d . . . C13 C 0.2181(5) -0.1048(7) 0.6989(8) 0.057(3) Uani 1 1 d . . . H13A H 0.2469 -0.1460 0.7105 0.069 Uiso 1 1 calc R . . C8 C 0.2977(4) -0.1170(6) 0.4886(8) 0.045(2) Uani 1 1 d . . . C14 C 0.1601(6) -0.1299(7) 0.6780(9) 0.056(3) Uani 1 1 d . . . C3 C 0.5076(4) 0.0872(6) 0.6322(7) 0.040(2) Uani 1 1 d . . . H3A H 0.5423 0.0632 0.6560 0.048 Uiso 1 1 calc R . . N12 N 0.1479(5) 0.1355(8) 0.9392(8) 0.071(3) Uani 1 1 d . . . N9 N 0.3745(5) 0.0779(6) 0.2835(8) 0.064(3) Uani 1 1 d . . . C15 C 0.1185(5) -0.0653(6) 0.6636(7) 0.045(2) Uani 1 1 d . . . C1 C 0.4477(4) 0.2102(7) 0.5897(7) 0.042(2) Uani 1 1 d . . . C20 C 0.0469(5) 0.2079(7) 0.6367(9) 0.054(3) Uani 1 1 d . . . C5 C 0.4496(4) -0.0578(7) 0.5942(7) 0.042(2) Uani 1 1 d . . . N3 N 0.3552(4) 0.1489(7) 0.7789(7) 0.064(3) Uani 1 1 d . . . O2 O 0.0190(4) -0.1206(6) 0.6318(8) 0.092(3) Uani 1 1 d . . . C21 C 0.0906(4) 0.0776(5) 0.6513(6) 0.0304(19) Uani 1 1 d . . . N6 N 0.1419(5) 0.0900(7) 0.4197(8) 0.076(3) Uani 1 1 d . . . C17 C 0.0377(5) 0.0333(7) 0.6345(8) 0.051(3) Uani 1 1 d . . . C16 C 0.0540(5) -0.0618(7) 0.6414(9) 0.058(3) Uani 1 1 d . . . C18 C -0.0133(5) 0.0798(8) 0.6171(9) 0.060(3) Uani 1 1 d . . . C19 C -0.0074(4) 0.1679(8) 0.6204(8) 0.055(3) Uani 1 1 d . . . H19A H -0.0409 0.2016 0.6115 0.066 Uiso 1 1 calc R . . H8 H 0.237(3) -0.014(4) 0.470(5) 0.010(17) Uiso 1 1 d . . . H4 H 0.437(4) 0.275(6) 0.585(6) 0.03(2) Uiso 1 1 d . . . H3 H 0.049(3) 0.271(5) 0.633(5) 0.015(18) Uiso 1 1 d . . . H2 H -0.055(5) 0.053(6) 0.602(7) 0.05(3) Uiso 1 1 d . . . H5 H 0.546(5) 0.195(7) 0.635(7) 0.05(3) Uiso 1 1 d . . . H6 H 0.359(4) -0.190(6) 0.545(7) 0.04(3) Uiso 1 1 d . . . H1 H 0.152(4) -0.189(7) 0.681(7) 0.04(3) Uiso 1 1 d . . . H7 H 0.276(6) -0.167(9) 0.452(10) 0.09(4) 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 0.0259(6) 0.0240(6) 0.0345(6) 0.0038(5) -0.0029(5) 0.0019(5) Co2 0.0245(6) 0.0259(6) 0.0363(7) 0.0032(5) -0.0019(5) -0.0007(4) N1 0.030(4) 0.037(4) 0.032(4) 0.006(3) -0.005(3) 0.000(3) N4 0.044(4) 0.022(4) 0.041(4) -0.004(3) -0.012(3) -0.006(3) N15 0.030(4) 0.029(4) 0.045(4) 0.003(3) 0.001(3) -0.004(3) N11 0.029(4) 0.047(5) 0.038(4) 0.002(4) -0.008(3) 0.002(4) N14 0.029(4) 0.036(4) 0.036(4) 0.009(3) -0.007(3) 0.001(3) N7 0.051(5) 0.030(4) 0.042(5) 0.003(4) 0.009(4) 0.006(4) N16 0.027(4) 0.033(4) 0.055(5) 0.003(4) -0.005(3) 0.005(3) N8 0.039(4) 0.039(5) 0.043(5) 0.005(4) -0.004(4) -0.003(4) N13 0.032(4) 0.028(4) 0.054(5) 0.000(3) -0.007(3) -0.006(3) N2 0.040(4) 0.041(4) 0.038(4) -0.002(4) -0.010(4) -0.003(4) N5 0.043(5) 0.047(5) 0.050(5) 0.009(4) -0.002(4) 0.008(4) O1 0.058(5) 0.054(5) 0.084(6) 0.012(4) -0.012(4) 0.024(4) C11 0.026(4) 0.036(5) 0.039(5) 0.001(4) -0.002(4) 0.002(4) C6 0.033(5) 0.042(5) 0.036(5) 0.002(4) -0.003(4) -0.001(4) C2 0.031(5) 0.055(6) 0.055(6) -0.014(5) 0.007(4) -0.016(5) N10 0.068(6) 0.044(5) 0.042(5) 0.000(4) 0.006(4) -0.021(4) C10 0.024(4) 0.033(5) 0.039(5) 0.001(4) -0.004(4) -0.005(3) C4 0.036(5) 0.045(5) 0.038(5) -0.001(4) -0.001(4) 0.006(4) C7 0.047(6) 0.027(5) 0.053(6) 0.004(4) 0.008(5) 0.002(4) C12 0.035(5) 0.060(7) 0.062(7) 0.005(6) -0.013(5) 0.014(5) C22 0.036(5) 0.026(4) 0.038(5) -0.004(4) -0.002(4) 0.003(4) C9 0.026(5) 0.041(5) 0.060(6) 0.002(5) -0.009(4) -0.006(4) C13 0.067(8) 0.043(6) 0.061(7) 0.008(5) -0.001(6) 0.025(6) C8 0.033(5) 0.037(5) 0.063(7) -0.001(5) -0.001(5) -0.007(4) C14 0.067(8) 0.031(6) 0.068(8) 0.005(5) -0.003(6) 0.005(5) C3 0.026(5) 0.053(6) 0.042(5) -0.005(4) -0.006(4) 0.000(4) N12 0.056(6) 0.092(8) 0.065(7) 0.031(6) 0.008(5) -0.005(6) N9 0.063(6) 0.054(6) 0.076(7) -0.021(5) 0.028(5) -0.003(5) C15 0.051(6) 0.032(5) 0.051(6) 0.008(4) -0.009(5) -0.004(4) C1 0.040(5) 0.040(5) 0.047(6) -0.003(4) 0.001(4) -0.005(4) C20 0.039(6) 0.041(6) 0.082(8) 0.013(6) 0.005(5) 0.007(5) C5 0.037(5) 0.050(6) 0.040(5) 0.006(4) 0.001(4) 0.019(4) N3 0.050(6) 0.093(8) 0.048(6) 0.015(5) -0.006(5) 0.012(5) O2 0.079(7) 0.057(6) 0.139(10) 0.013(6) -0.028(6) -0.028(5) C21 0.025(4) 0.021(4) 0.044(5) 0.003(4) -0.003(4) 0.001(3) N6 0.069(7) 0.080(8) 0.081(8) -0.026(6) -0.034(6) -0.017(6) C17 0.049(6) 0.045(6) 0.058(7) 0.007(5) -0.007(5) -0.014(5) C16 0.058(7) 0.049(6) 0.067(8) 0.001(5) -0.008(6) -0.022(6) C18 0.030(6) 0.068(8) 0.082(9) 0.015(7) -0.005(5) -0.007(5) C19 0.028(5) 0.068(8) 0.070(7) 0.014(6) -0.005(5) 0.015(5) _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 N7 2.061(8) . ? Co1 N1 2.087(7) . ? Co1 N4 2.216(8) . ? Co1 N14 2.222(7) . ? Co1 N4 2.229(7) 7_556 ? Co1 N13 2.310(7) . ? Co2 N10 2.033(9) . ? Co2 N1 2.120(7) . ? Co2 N7 2.125(8) 7_556 ? Co2 N16 2.211(7) . ? Co2 N4 2.267(8) . ? Co2 N15 2.293(7) . ? N1 N2 1.207(10) . ? N4 N5 1.236(11) . ? N4 Co1 2.229(7) 7_556 ? N15 C22 1.333(11) . ? N15 C12 1.343(12) . ? N11 N12 1.161(12) . ? N11 N10 1.208(11) . ? N14 C9 1.349(12) . ? N14 C10 1.350(11) . ? N7 N8 1.225(11) . ? N7 Co2 2.125(8) 7_556 ? N16 C21 1.318(11) . ? N16 C20 1.390(12) . ? N8 N9 1.148(12) . ? N13 C11 1.351(11) . ? N13 C1 1.374(12) . ? N2 N3 1.164(11) . ? N5 N6 1.174(12) . ? O1 C5 1.228(11) . ? C11 C4 1.387(12) . ? C11 C10 1.458(12) . ? C6 C7 1.372(13) . ? C6 C10 1.383(13) . ? C6 C5 1.521(13) . ? C2 C3 1.381(15) . ? C2 C1 1.406(15) . ? C2 H5 1.09(11) . ? C4 C3 1.398(13) . ? C4 C5 1.497(14) . ? C7 C8 1.374(14) . ? C7 H6 0.92(10) . ? C12 C13 1.376(16) . ? C12 H12A 0.9300 . ? C22 C15 1.374(13) . ? C22 C21 1.471(11) . ? C9 C8 1.401(14) . ? C9 H8 0.98(7) . ? C13 C14 1.398(17) . ? C13 H13A 0.9300 . ? C8 H7 1.05(14) . ? C14 C15 1.394(15) . ? C14 H1 0.95(10) . ? C3 H3A 0.9300 . ? C15 C16 1.489(15) . ? C1 H4 1.04(9) . ? C20 C19 1.394(15) . ? C20 H3 0.99(8) . ? O2 C16 1.219(13) . ? C21 C17 1.402(13) . ? C17 C18 1.382(15) . ? C17 C16 1.538(16) . ? C18 C19 1.388(17) . ? C18 H2 1.04(10) . ? C19 H19A 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 N7 Co1 N1 172.3(3) . . ? N7 Co1 N4 98.7(3) . . ? N1 Co1 N4 80.4(3) . . ? N7 Co1 N14 89.3(3) . . ? N1 Co1 N14 98.4(3) . . ? N4 Co1 N14 98.0(3) . . ? N7 Co1 N4 80.5(3) . 7_556 ? N1 Co1 N4 91.8(3) . 7_556 ? N4 Co1 N4 82.5(3) . 7_556 ? N14 Co1 N4 169.8(3) . 7_556 ? N7 Co1 N13 96.7(3) . . ? N1 Co1 N13 84.6(3) . . ? N4 Co1 N13 164.5(3) . . ? N14 Co1 N13 80.2(3) . . ? N4 Co1 N13 102.0(3) 7_556 . ? N10 Co2 N1 95.3(3) . . ? N10 Co2 N7 95.0(3) . 7_556 ? N1 Co2 N7 95.4(3) . 7_556 ? N10 Co2 N16 98.4(3) . . ? N1 Co2 N16 163.4(3) . . ? N7 Co2 N16 92.8(3) 7_556 . ? N10 Co2 N4 170.3(3) . . ? N1 Co2 N4 78.5(3) . . ? N7 Co2 N4 78.3(3) 7_556 . ? N16 Co2 N4 89.1(3) . . ? N10 Co2 N15 94.5(3) . . ? N1 Co2 N15 90.1(3) . . ? N7 Co2 N15 168.6(3) 7_556 . ? N16 Co2 N15 79.4(3) . . ? N4 Co2 N15 93.1(3) . . ? N2 N1 Co1 124.1(6) . . ? N2 N1 Co2 125.2(6) . . ? Co1 N1 Co2 104.8(3) . . ? N5 N4 Co1 122.6(6) . . ? N5 N4 Co1 118.8(6) . 7_556 ? Co1 N4 Co1 97.5(3) . 7_556 ? N5 N4 Co2 120.4(6) . . ? Co1 N4 Co2 96.1(3) . . ? Co1 N4 Co2 95.6(3) 7_556 . ? C22 N15 C12 113.8(8) . . ? C22 N15 Co2 106.9(5) . . ? C12 N15 Co2 139.2(7) . . ? N12 N11 N10 173.3(11) . . ? C9 N14 C10 114.2(8) . . ? C9 N14 Co1 137.6(6) . . ? C10 N14 Co1 108.2(6) . . ? N8 N7 Co1 124.1(6) . . ? N8 N7 Co2 125.0(6) . 7_556 ? Co1 N7 Co2 105.4(3) . 7_556 ? C21 N16 C20 114.4(8) . . ? C21 N16 Co2 109.2(5) . . ? C20 N16 Co2 136.2(7) . . ? N9 N8 N7 177.8(10) . . ? C11 N13 C1 113.0(8) . . ? C11 N13 Co1 105.4(5) . . ? C1 N13 Co1 140.4(6) . . ? N3 N2 N1 178.2(10) . . ? N6 N5 N4 176.9(11) . . ? N13 C11 C4 127.8(8) . . ? N13 C11 C10 122.6(8) . . ? C4 C11 C10 109.6(8) . . ? C7 C6 C10 118.1(8) . . ? C7 C6 C5 135.6(9) . . ? C10 C6 C5 106.2(8) . . ? C3 C2 C1 121.1(9) . . ? C3 C2 H5 100(6) . . ? C1 C2 H5 137(6) . . ? N11 N10 Co2 127.3(7) . . ? N14 C10 C6 126.4(8) . . ? N14 C10 C11 122.9(8) . . ? C6 C10 C11 110.7(7) . . ? C11 C4 C3 117.8(9) . . ? C11 C4 C5 107.4(8) . . ? C3 C4 C5 134.8(9) . . ? C6 C7 C8 117.5(9) . . ? C6 C7 H6 124(6) . . ? C8 C7 H6 116(6) . . ? N15 C12 C13 123.5(10) . . ? N15 C12 H12A 118.3 . . ? C13 C12 H12A 118.3 . . ? N15 C22 C15 128.5(8) . . ? N15 C22 C21 121.5(8) . . ? C15 C22 C21 110.0(8) . . ? N14 C9 C8 122.6(8) . . ? N14 C9 H8 110(4) . . ? C8 C9 H8 126(4) . . ? C12 C13 C14 120.7(10) . . ? C12 C13 H13A 119.7 . . ? C14 C13 H13A 119.7 . . ? C7 C8 C9 121.0(9) . . ? C7 C8 H7 116(7) . . ? C9 C8 H7 121(7) . . ? C15 C14 C13 117.1(10) . . ? C15 C14 H1 126(6) . . ? C13 C14 H1 117(6) . . ? C2 C3 C4 117.0(9) . . ? C2 C3 H3A 121.5 . . ? C4 C3 H3A 121.5 . . ? C22 C15 C14 116.4(9) . . ? C22 C15 C16 108.1(9) . . ? C14 C15 C16 135.5(10) . . ? N13 C1 C2 123.2(9) . . ? N13 C1 H4 110(5) . . ? C2 C1 H4 127(5) . . ? N16 C20 C19 121.3(10) . . ? N16 C20 H3 119(4) . . ? C19 C20 H3 119(4) . . ? O1 C5 C4 126.9(10) . . ? O1 C5 C6 127.0(10) . . ? C4 C5 C6 106.1(7) . . ? N16 C21 C17 127.2(8) . . ? N16 C21 C22 122.6(8) . . ? C17 C21 C22 110.1(8) . . ? C18 C17 C21 118.5(10) . . ? C18 C17 C16 136.2(10) . . ? C21 C17 C16 105.4(9) . . ? O2 C16 C15 128.9(11) . . ? O2 C16 C17 124.6(11) . . ? C15 C16 C17 106.4(8) . . ? C17 C18 C19 116.0(10) . . ? C17 C18 H2 124(6) . . ? C19 C18 H2 120(6) . . ? C18 C19 C20 122.5(10) . . ? C18 C19 H19A 118.7 . . ? C20 C19 H19A 118.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N7 Co1 N1 N2 -119(2) . . . . ? N4 Co1 N1 N2 157.7(8) . . . . ? N14 Co1 N1 N2 60.9(8) . . . . ? N4 Co1 N1 N2 -120.2(7) 7_556 . . . ? N13 Co1 N1 N2 -18.4(7) . . . . ? N7 Co1 N1 Co2 87(2) . . . . ? N4 Co1 N1 Co2 3.7(3) . . . . ? N14 Co1 N1 Co2 -93.1(3) . . . . ? N4 Co1 N1 Co2 85.8(3) 7_556 . . . ? N13 Co1 N1 Co2 -172.4(3) . . . . ? N10 Co2 N1 N2 30.3(8) . . . . ? N7 Co2 N1 N2 125.9(8) 7_556 . . . ? N16 Co2 N1 N2 -114.8(11) . . . . ? N4 Co2 N1 N2 -157.3(8) . . . . ? N15 Co2 N1 N2 -64.2(8) . . . . ? N10 Co2 N1 Co1 -176.1(4) . . . . ? N7 Co2 N1 Co1 -80.5(3) 7_556 . . . ? N16 Co2 N1 Co1 38.8(11) . . . . ? N4 Co2 N1 Co1 -3.6(3) . . . . ? N15 Co2 N1 Co1 89.5(3) . . . . ? N7 Co1 N4 N5 52.2(7) . . . . ? N1 Co1 N4 N5 -135.6(7) . . . . ? N14 Co1 N4 N5 -38.4(7) . . . . ? N4 Co1 N4 N5 131.3(8) 7_556 . . . ? N13 Co1 N4 N5 -120.7(10) . . . . ? N7 Co1 N4 Co1 -79.1(3) . . . 7_556 ? N1 Co1 N4 Co1 93.1(3) . . . 7_556 ? N14 Co1 N4 Co1 -169.7(3) . . . 7_556 ? N4 Co1 N4 Co1 0.0 7_556 . . 7_556 ? N13 Co1 N4 Co1 107.9(9) . . . 7_556 ? N7 Co1 N4 Co2 -175.6(3) . . . . ? N1 Co1 N4 Co2 -3.4(3) . . . . ? N14 Co1 N4 Co2 93.8(3) . . . . ? N4 Co1 N4 Co2 -96.5(3) 7_556 . . . ? N13 Co1 N4 Co2 11.4(11) . . . . ? N10 Co2 N4 N5 -171.9(19) . . . . ? N1 Co2 N4 N5 137.0(7) . . . . ? N7 Co2 N4 N5 -125.0(7) 7_556 . . . ? N16 Co2 N4 N5 -31.9(7) . . . . ? N15 Co2 N4 N5 47.5(7) . . . . ? N10 Co2 N4 Co1 54(2) . . . . ? N1 Co2 N4 Co1 3.3(3) . . . . ? N7 Co2 N4 Co1 101.4(3) 7_556 . . . ? N16 Co2 N4 Co1 -165.5(3) . . . . ? N15 Co2 N4 Co1 -86.2(3) . . . . ? N10 Co2 N4 Co1 -44(2) . . . 7_556 ? N1 Co2 N4 Co1 -94.9(3) . . . 7_556 ? N7 Co2 N4 Co1 3.2(3) 7_556 . . 7_556 ? N16 Co2 N4 Co1 96.3(3) . . . 7_556 ? N15 Co2 N4 Co1 175.6(3) . . . 7_556 ? N10 Co2 N15 C22 102.2(6) . . . . ? N1 Co2 N15 C22 -162.5(6) . . . . ? N7 Co2 N15 C22 -43.4(17) 7_556 . . . ? N16 Co2 N15 C22 4.5(6) . . . . ? N4 Co2 N15 C22 -84.0(6) . . . . ? N10 Co2 N15 C12 -82.1(11) . . . . ? N1 Co2 N15 C12 13.2(11) . . . . ? N7 Co2 N15 C12 132.4(15) 7_556 . . . ? N16 Co2 N15 C12 -179.8(11) . . . . ? N4 Co2 N15 C12 91.8(11) . . . . ? N7 Co1 N14 C9 -77.1(10) . . . . ? N1 Co1 N14 C9 103.0(10) . . . . ? N4 Co1 N14 C9 21.6(10) . . . . ? N4 Co1 N14 C9 -70.4(19) 7_556 . . . ? N13 Co1 N14 C9 -174.0(10) . . . . ? N7 Co1 N14 C10 101.6(6) . . . . ? N1 Co1 N14 C10 -78.4(6) . . . . ? N4 Co1 N14 C10 -159.8(6) . . . . ? N4 Co1 N14 C10 108.3(15) 7_556 . . . ? N13 Co1 N14 C10 4.7(6) . . . . ? N1 Co1 N7 N8 150(2) . . . . ? N4 Co1 N7 N8 -127.8(8) . . . . ? N14 Co1 N7 N8 -29.8(8) . . . . ? N4 Co1 N7 N8 151.4(8) 7_556 . . . ? N13 Co1 N7 N8 50.3(8) . . . . ? N1 Co1 N7 Co2 -5(3) . . . 7_556 ? N4 Co1 N7 Co2 77.2(4) . . . 7_556 ? N14 Co1 N7 Co2 175.2(4) . . . 7_556 ? N4 Co1 N7 Co2 -3.6(3) 7_556 . . 7_556 ? N13 Co1 N7 Co2 -104.7(3) . . . 7_556 ? N10 Co2 N16 C21 -98.3(7) . . . . ? N1 Co2 N16 C21 46.6(13) . . . . ? N7 Co2 N16 C21 166.3(7) 7_556 . . . ? N4 Co2 N16 C21 88.0(7) . . . . ? N15 Co2 N16 C21 -5.3(6) . . . . ? N10 Co2 N16 C20 86.3(11) . . . . ? N1 Co2 N16 C20 -128.8(12) . . . . ? N7 Co2 N16 C20 -9.2(11) 7_556 . . . ? N4 Co2 N16 C20 -87.4(11) . . . . ? N15 Co2 N16 C20 179.3(11) . . . . ? Co1 N7 N8 N9 75(29) . . . . ? Co2 N7 N8 N9 -135(29) 7_556 . . . ? N7 Co1 N13 C11 -95.1(6) . . . . ? N1 Co1 N13 C11 92.6(6) . . . . ? N4 Co1 N13 C11 77.9(12) . . . . ? N14 Co1 N13 C11 -6.9(6) . . . . ? N4 Co1 N13 C11 -176.7(6) 7_556 . . . ? N7 Co1 N13 C1 98.8(11) . . . . ? N1 Co1 N13 C1 -73.5(11) . . . . ? N4 Co1 N13 C1 -88.2(14) . . . . ? N14 Co1 N13 C1 -173.0(11) . . . . ? N4 Co1 N13 C1 17.2(11) 7_556 . . . ? Co1 N1 N2 N3 110(32) . . . . ? Co2 N1 N2 N3 -101(32) . . . . ? Co1 N4 N5 N6 157(19) . . . . ? Co1 N4 N5 N6 -81(20) 7_556 . . . ? Co2 N4 N5 N6 36(20) . . . . ? C1 N13 C11 C4 -3.8(14) . . . . ? Co1 N13 C11 C4 -174.2(8) . . . . ? C1 N13 C11 C10 179.0(9) . . . . ? Co1 N13 C11 C10 8.6(11) . . . . ? N12 N11 N10 Co2 -177(100) . . . . ? N1 Co2 N10 N11 -125.1(10) . . . . ? N7 Co2 N10 N11 139.0(10) 7_556 . . . ? N16 Co2 N10 N11 45.4(10) . . . . ? N4 Co2 N10 N11 -175.1(15) . . . . ? N15 Co2 N10 N11 -34.5(10) . . . . ? C9 N14 C10 C6 -4.6(14) . . . . ? Co1 N14 C10 C6 176.4(8) . . . . ? C9 N14 C10 C11 177.1(9) . . . . ? Co1 N14 C10 C11 -1.9(10) . . . . ? C7 C6 C10 N14 5.0(15) . . . . ? C5 C6 C10 N14 -176.9(9) . . . . ? C7 C6 C10 C11 -176.5(9) . . . . ? C5 C6 C10 C11 1.6(10) . . . . ? N13 C11 C10 N14 -5.3(14) . . . . ? C4 C11 C10 N14 177.1(8) . . . . ? N13 C11 C10 C6 176.2(9) . . . . ? C4 C11 C10 C6 -1.4(11) . . . . ? N13 C11 C4 C3 2.8(15) . . . . ? C10 C11 C4 C3 -179.8(8) . . . . ? N13 C11 C4 C5 -176.9(9) . . . . ? C10 C11 C4 C5 0.5(11) . . . . ? C10 C6 C7 C8 -2.6(14) . . . . ? C5 C6 C7 C8 179.9(10) . . . . ? C22 N15 C12 C13 1.9(15) . . . . ? Co2 N15 C12 C13 -173.7(8) . . . . ? C12 N15 C22 C15 -2.5(15) . . . . ? Co2 N15 C22 C15 174.5(9) . . . . ? C12 N15 C22 C21 179.8(9) . . . . ? Co2 N15 C22 C21 -3.2(10) . . . . ? C10 N14 C9 C8 2.1(14) . . . . ? Co1 N14 C9 C8 -179.2(8) . . . . ? N15 C12 C13 C14 0.0(19) . . . . ? C6 C7 C8 C9 0.5(16) . . . . ? N14 C9 C8 C7 -0.3(17) . . . . ? C12 C13 C14 C15 -1.5(18) . . . . ? C1 C2 C3 C4 0.1(15) . . . . ? C11 C4 C3 C2 -0.7(14) . . . . ? C5 C4 C3 C2 178.9(10) . . . . ? N15 C22 C15 C14 1.1(16) . . . . ? C21 C22 C15 C14 179.0(9) . . . . ? N15 C22 C15 C16 -178.7(10) . . . . ? C21 C22 C15 C16 -0.7(12) . . . . ? C13 C14 C15 C22 1.0(16) . . . . ? C13 C14 C15 C16 -179.3(12) . . . . ? C11 N13 C1 C2 3.0(14) . . . . ? Co1 N13 C1 C2 168.4(8) . . . . ? C3 C2 C1 N13 -1.4(16) . . . . ? C21 N16 C20 C19 -0.5(16) . . . . ? Co2 N16 C20 C19 174.8(8) . . . . ? C11 C4 C5 O1 178.2(10) . . . . ? C3 C4 C5 O1 -1.4(19) . . . . ? C11 C4 C5 C6 0.4(10) . . . . ? C3 C4 C5 C6 -179.2(11) . . . . ? C7 C6 C5 O1 -1.4(19) . . . . ? C10 C6 C5 O1 -179.0(10) . . . . ? C7 C6 C5 C4 176.4(11) . . . . ? C10 C6 C5 C4 -1.2(10) . . . . ? C20 N16 C21 C17 1.3(15) . . . . ? Co2 N16 C21 C17 -175.3(9) . . . . ? C20 N16 C21 C22 -177.8(9) . . . . ? Co2 N16 C21 C22 5.6(11) . . . . ? N15 C22 C21 N16 -1.6(14) . . . . ? C15 C22 C21 N16 -179.7(9) . . . . ? N15 C22 C21 C17 179.1(9) . . . . ? C15 C22 C21 C17 1.1(12) . . . . ? N16 C21 C17 C18 -0.2(17) . . . . ? C22 C21 C17 C18 179.0(10) . . . . ? N16 C21 C17 C16 179.9(10) . . . . ? C22 C21 C17 C16 -0.9(12) . . . . ? C22 C15 C16 O2 -178.4(13) . . . . ? C14 C15 C16 O2 2(2) . . . . ? C22 C15 C16 C17 0.2(12) . . . . ? C14 C15 C16 C17 -179.5(13) . . . . ? C18 C17 C16 O2 -1(2) . . . . ? C21 C17 C16 O2 179.1(13) . . . . ? C18 C17 C16 C15 -179.4(14) . . . . ? C21 C17 C16 C15 0.4(12) . . . . ? C21 C17 C18 C19 -1.6(17) . . . . ? C16 C17 C18 C19 178.2(13) . . . . ? C17 C18 C19 C20 2.4(19) . . . . ? N16 C20 C19 C18 -1.4(19) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 1.316 _refine_diff_density_min -1.339 _refine_diff_density_rms 0.130 _database_code_depnum_ccdc_archive 'CCDC 829020'