# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email pcheng@nankai.edu.cn _publ_contact_author_name 'Peng Cheng' _publ_author_name 'Peng Cheng' data_1 _database_code_depnum_ccdc_archive 'CCDC 776487' #TrackingRef '- crystal_data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H28 Cl Co0.50 N12 O6' _chemical_formula_weight 645.50 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.2749(17) _cell_length_b 11.868(2) _cell_length_c 15.649(3) _cell_angle_alpha 72.52(3) _cell_angle_beta 78.69(3) _cell_angle_gamma 81.16(3) _cell_volume 1430.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11910 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 25.01 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 669 _exptl_absorpt_coefficient_mu 0.476 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9766 _exptl_absorpt_correction_T_max 0.9905 _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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11910 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5026 _reflns_number_gt 4153 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+1.9005P] 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 5026 _refine_ls_number_parameters 409 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1378 _refine_ls_wR_factor_gt 0.1281 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.0000 1.0000 0.5000 0.02797(18) Uani 1 2 d S . . C1 C 0.3371(4) 0.9609(4) 0.3747(3) 0.0519(10) Uani 1 1 d . . . H1 H 0.2904 0.9989 0.3227 0.062 Uiso 1 1 calc R . . N2 N 0.5196(4) 0.8680(3) 0.4603(2) 0.0599(9) Uani 1 1 d . . . C3 C 0.6204(4) 0.9056(4) 0.2964(3) 0.0505(9) Uani 1 1 d . . . H3A H 0.7158 0.8538 0.3175 0.061 Uiso 1 1 calc R . . H3B H 0.6559 0.9833 0.2634 0.061 Uiso 1 1 calc R . . C4 C 0.5509(4) 0.8562(3) 0.2350(2) 0.0434(8) Uani 1 1 d . . . C5 C 0.5197(5) 0.7378(3) 0.2631(3) 0.0537(10) Uani 1 1 d . . . H5 H 0.5545 0.6876 0.3158 0.064 Uiso 1 1 calc R . . C6 C 0.4375(5) 0.6947(4) 0.2133(3) 0.0583(10) Uani 1 1 d . . . H6 H 0.4187 0.6151 0.2323 0.070 Uiso 1 1 calc R . . C7 C 0.3824(5) 0.7681(3) 0.1353(2) 0.0489(9) Uani 1 1 d . . . C8 C 0.4183(5) 0.8836(3) 0.1063(2) 0.0507(9) Uani 1 1 d . . . H8 H 0.3851 0.9335 0.0530 0.061 Uiso 1 1 calc R . . C9 C 0.5035(5) 0.9272(3) 0.1554(3) 0.0504(9) Uani 1 1 d . . . H9 H 0.5289 1.0055 0.1340 0.060 Uiso 1 1 calc R . . C10 C 0.2804(6) 0.7227(4) 0.0850(3) 0.0646(12) Uani 1 1 d . . . H10A H 0.2266 0.7895 0.0437 0.078 Uiso 1 1 calc R . . H10B H 0.3526 0.6751 0.0494 0.078 Uiso 1 1 calc R . . C12 C 0.1473(6) 0.5358(4) 0.1711(3) 0.0569(10) Uani 1 1 d . . . H12 H 0.2210 0.4831 0.1454 0.068 Uiso 1 1 calc R . . N5 N 0.0309(4) 0.7018(3) 0.1983(2) 0.0607(9) Uani 1 1 d . . . C13 C -0.1546(4) 0.7571(3) 0.5564(2) 0.0337(7) Uani 1 1 d . . . H13 H -0.2046 0.7687 0.6122 0.040 Uiso 1 1 calc R . . N8 N -0.0795(4) 0.6745(3) 0.44529(19) 0.0438(7) Uani 1 1 d . . . C15 C -0.2463(4) 0.5555(3) 0.5818(2) 0.0388(8) Uani 1 1 d . . . H15A H -0.2967 0.5637 0.6413 0.047 Uiso 1 1 calc R . . H15B H -0.1617 0.4885 0.5903 0.047 Uiso 1 1 calc R . . C16 C -0.3772(4) 0.5286(3) 0.5376(2) 0.0339(7) Uani 1 1 d . . . C17 C -0.3370(4) 0.4602(3) 0.4775(2) 0.0419(8) Uani 1 1 d . . . H17 H -0.2271 0.4324 0.4620 0.050 Uiso 1 1 calc R . . C18 C -0.5413(4) 0.5672(3) 0.5598(2) 0.0412(8) Uani 1 1 d . . . H18 H -0.5708 0.6125 0.6008 0.049 Uiso 1 1 calc R . . C19 C 0.1215(5) 0.1405(3) 0.1527(2) 0.0498(9) Uani 1 1 d . . . H19 H 0.1670 0.1824 0.1822 0.060 Uiso 1 1 calc R . . N11 N 0.0460(4) 0.0919(3) 0.0440(2) 0.0532(8) Uani 1 1 d . . . C21 C 0.1868(5) 0.2732(3) -0.0055(2) 0.0470(9) Uani 1 1 d . . . H21A H 0.1872 0.2625 -0.0646 0.056 Uiso 1 1 calc R . . H21B H 0.3004 0.2769 0.0000 0.056 Uiso 1 1 calc R . . C22 C 0.0877(4) 0.3892(3) -0.0003(2) 0.0384(8) Uani 1 1 d . . . C23 C -0.0717(4) 0.3973(3) 0.0465(2) 0.0436(8) Uani 1 1 d . . . H23 H -0.1213 0.3282 0.0782 0.052 Uiso 1 1 calc R . . C24 C 0.1585(4) 0.4938(3) -0.0470(2) 0.0433(8) Uani 1 1 d . . . H24 H 0.2656 0.4905 -0.0789 0.052 Uiso 1 1 calc R . . Cl1 Cl 0.50438(12) 0.28211(10) 0.19426(7) 0.0569(3) Uani 1 1 d . . . H1A H 0.068(6) 0.8486(14) 0.649(2) 0.085 Uiso 1 1 d D . . H6A H 0.929(5) 0.354(3) 0.281(3) 0.11(2) Uiso 1 1 d D . . H1B H 0.002(5) 0.955(3) 0.6762(17) 0.057(12) Uiso 1 1 d D . . H6B H 0.779(4) 0.308(4) 0.277(3) 0.075(16) Uiso 1 1 d D . . N1 N 0.2565(3) 0.9468(2) 0.45702(18) 0.0356(6) Uani 1 1 d . . . C2 C 0.3743(5) 0.8903(4) 0.5067(3) 0.0586(11) Uani 1 1 d . . . H2 H 0.3545 0.8684 0.5698 0.070 Uiso 1 1 calc R . . N3 N 0.4925(3) 0.9150(2) 0.37404(19) 0.0407(7) Uani 1 1 d . . . C11 C -0.0448(5) 0.6095(4) 0.2496(3) 0.0588(11) Uani 1 1 d . . . H11 H -0.1380 0.6163 0.2926 0.071 Uiso 1 1 calc R . . N4 N 0.0212(5) 0.5050(3) 0.2359(2) 0.0603(9) Uani 1 1 d . . . N6 N 0.1553(4) 0.6512(3) 0.1477(2) 0.0486(8) Uani 1 1 d . . . N7 N -0.0621(3) 0.8321(2) 0.49301(17) 0.0334(6) Uani 1 1 d . . . C14 C -0.0200(4) 0.7770(3) 0.4262(2) 0.0410(8) Uani 1 1 d . . . H14 H 0.0458 0.8093 0.3713 0.049 Uiso 1 1 calc R . . N9 N -0.1667(3) 0.6635(2) 0.52990(17) 0.0323(6) Uani 1 1 d . . . N10 N 0.0475(4) 0.0436(3) 0.19390(19) 0.0503(8) Uani 1 1 d . . . C20 C 0.0045(5) 0.0178(3) 0.1236(3) 0.0540(10) Uani 1 1 d . . . H20 H -0.0506 -0.0481 0.1312 0.065 Uiso 1 1 calc R . . N12 N 0.1231(4) 0.1706(2) 0.06448(18) 0.0396(7) Uani 1 1 d . . . O1 O 0.0298(3) 0.9217(2) 0.63380(15) 0.0441(6) Uani 1 1 d D . . O2 O 0.5367(5) 0.3775(4) 0.2220(3) 0.1056(13) Uani 1 1 d . . . O3 O 0.6492(6) 0.2057(4) 0.1898(4) 0.153(2) Uani 1 1 d . . . O4 O 0.4689(6) 0.3278(6) 0.1062(3) 0.146(2) Uani 1 1 d . . . O5 O 0.3680(5) 0.2302(5) 0.2492(3) 0.1321(19) Uani 1 1 d . . . O6 O 0.8598(4) 0.3027(2) 0.3046(2) 0.0598(7) Uani 1 1 d 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 0.0309(3) 0.0263(3) 0.0277(3) -0.0076(2) -0.0039(2) -0.0066(2) C1 0.0328(19) 0.072(3) 0.041(2) -0.0057(19) -0.0049(16) 0.0042(18) N2 0.0442(19) 0.073(2) 0.053(2) -0.0067(17) -0.0105(16) 0.0056(16) C3 0.0300(18) 0.064(2) 0.057(2) -0.022(2) 0.0050(17) -0.0068(17) C4 0.0284(17) 0.047(2) 0.050(2) -0.0134(17) 0.0057(15) -0.0029(15) C5 0.052(2) 0.049(2) 0.052(2) -0.0007(18) -0.0091(19) -0.0069(18) C6 0.065(3) 0.047(2) 0.062(3) -0.008(2) -0.008(2) -0.020(2) C7 0.046(2) 0.057(2) 0.0387(19) -0.0106(18) 0.0048(16) -0.0119(18) C8 0.052(2) 0.055(2) 0.0362(19) -0.0016(17) -0.0012(17) -0.0077(18) C9 0.050(2) 0.042(2) 0.051(2) -0.0060(18) 0.0024(18) -0.0069(17) C10 0.065(3) 0.087(3) 0.045(2) -0.020(2) 0.003(2) -0.027(2) C12 0.068(3) 0.053(3) 0.059(2) -0.026(2) -0.020(2) -0.001(2) N5 0.064(2) 0.054(2) 0.058(2) -0.0171(17) 0.0065(18) -0.0097(17) C13 0.0355(17) 0.0353(17) 0.0344(17) -0.0145(14) -0.0028(14) -0.0093(14) N8 0.0524(18) 0.0434(17) 0.0407(16) -0.0194(13) 0.0015(14) -0.0154(14) C15 0.046(2) 0.0290(17) 0.0429(19) -0.0033(14) -0.0135(16) -0.0136(14) C16 0.0414(19) 0.0257(16) 0.0366(17) -0.0055(13) -0.0086(14) -0.0127(14) C17 0.0332(18) 0.046(2) 0.051(2) -0.0210(17) -0.0033(16) -0.0058(15) C18 0.045(2) 0.0386(19) 0.049(2) -0.0242(16) -0.0054(16) -0.0093(15) C19 0.068(3) 0.048(2) 0.0385(19) -0.0145(17) -0.0137(18) -0.0094(19) N11 0.079(2) 0.0461(18) 0.0411(17) -0.0155(15) -0.0098(16) -0.0195(17) C21 0.055(2) 0.044(2) 0.0392(19) -0.0109(16) 0.0021(17) -0.0104(17) C22 0.047(2) 0.0377(18) 0.0309(16) -0.0075(14) -0.0063(15) -0.0102(15) C23 0.048(2) 0.041(2) 0.0394(19) -0.0051(15) 0.0015(16) -0.0184(16) C24 0.0400(19) 0.047(2) 0.0386(19) -0.0077(16) 0.0036(15) -0.0127(16) Cl1 0.0488(6) 0.0685(7) 0.0569(6) -0.0213(5) 0.0022(5) -0.0224(5) N1 0.0328(15) 0.0344(15) 0.0402(15) -0.0101(12) -0.0057(13) -0.0056(12) C2 0.046(2) 0.078(3) 0.041(2) -0.007(2) -0.0075(18) 0.004(2) N3 0.0322(15) 0.0450(17) 0.0436(16) -0.0109(14) -0.0048(13) -0.0043(13) C11 0.053(2) 0.067(3) 0.054(2) -0.013(2) 0.000(2) -0.016(2) N4 0.076(3) 0.055(2) 0.054(2) -0.0076(17) -0.0210(19) -0.0209(19) N6 0.0540(19) 0.053(2) 0.0419(17) -0.0169(15) -0.0025(15) -0.0144(15) N7 0.0362(15) 0.0318(14) 0.0340(14) -0.0096(12) -0.0063(12) -0.0074(11) C14 0.044(2) 0.0413(19) 0.0392(18) -0.0137(15) 0.0017(15) -0.0142(16) N9 0.0351(14) 0.0307(14) 0.0343(14) -0.0094(11) -0.0075(12) -0.0097(11) N10 0.070(2) 0.0423(18) 0.0365(16) -0.0098(14) -0.0058(15) -0.0060(16) C20 0.075(3) 0.043(2) 0.048(2) -0.0164(18) -0.002(2) -0.0183(19) N12 0.0531(18) 0.0332(15) 0.0341(15) -0.0110(12) -0.0060(13) -0.0070(13) O1 0.0651(17) 0.0347(13) 0.0306(12) -0.0074(11) -0.0105(12) 0.0011(12) O2 0.115(3) 0.103(3) 0.123(3) -0.058(3) -0.009(3) -0.043(2) O3 0.093(3) 0.080(3) 0.258(7) -0.029(3) 0.001(4) 0.004(2) O4 0.137(4) 0.246(6) 0.059(2) -0.043(3) -0.011(2) -0.040(4) O5 0.119(3) 0.208(5) 0.091(3) -0.068(3) 0.050(2) -0.117(4) O6 0.0632(19) 0.0422(16) 0.0697(19) -0.0011(13) -0.0211(16) -0.0080(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.067(2) . ? Co1 O1 2.067(2) 2_576 ? Co1 N1 2.154(3) 2_576 ? Co1 N1 2.154(3) . ? Co1 N7 2.171(3) . ? Co1 N7 2.171(3) 2_576 ? C1 N1 1.304(4) . ? C1 N3 1.317(4) . ? C1 H1 0.9300 . ? N2 C2 1.311(5) . ? N2 N3 1.346(4) . ? C3 N3 1.467(4) . ? C3 C4 1.502(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C9 1.369(5) . ? C4 C5 1.390(5) . ? C5 C6 1.373(6) . ? C5 H5 0.9300 . ? C6 C7 1.383(5) . ? C6 H6 0.9300 . ? C7 C8 1.369(5) . ? C7 C10 1.509(6) . ? C8 C9 1.385(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 N6 1.457(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 N4 1.315(5) . ? C12 N6 1.316(5) . ? C12 H12 0.9300 . ? N5 C11 1.312(5) . ? N5 N6 1.351(4) . ? C13 N7 1.321(4) . ? C13 N9 1.321(4) . ? C13 H13 0.9300 . ? N8 C14 1.311(4) . ? N8 N9 1.357(4) . ? C15 N9 1.470(4) . ? C15 C16 1.512(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C18 1.377(5) . ? C16 C17 1.381(5) . ? C17 C18 1.380(5) 2_466 ? C17 H17 0.9300 . ? C18 C17 1.380(5) 2_466 ? C18 H18 0.9300 . ? C19 N12 1.317(4) . ? C19 N10 1.315(5) . ? C19 H19 0.9300 . ? N11 C20 1.308(5) . ? N11 N12 1.352(4) . ? C21 N12 1.459(4) . ? C21 C22 1.506(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C24 1.389(5) . ? C22 C23 1.383(5) . ? C23 C24 1.380(5) 2_565 ? C23 H23 0.9300 . ? C24 C23 1.380(5) 2_565 ? C24 H24 0.9300 . ? Cl1 O5 1.381(3) . ? Cl1 O3 1.391(4) . ? Cl1 O4 1.393(4) . ? Cl1 O2 1.405(4) . ? N1 C2 1.337(5) . ? C2 H2 0.9300 . ? C11 N4 1.337(5) . ? C11 H11 0.9300 . ? N7 C14 1.356(4) . ? C14 H14 0.9300 . ? N10 C20 1.349(5) . ? C20 H20 0.9300 . ? O1 H1A 0.854(10) . ? O1 H1B 0.847(10) . ? O6 H6A 0.851(10) . ? O6 H6B 0.847(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O1 180.0 . 2_576 ? O1 Co1 N1 90.06(11) . 2_576 ? O1 Co1 N1 89.94(11) 2_576 2_576 ? O1 Co1 N1 89.94(11) . . ? O1 Co1 N1 90.06(11) 2_576 . ? N1 Co1 N1 180.0 2_576 . ? O1 Co1 N7 89.31(10) . . ? O1 Co1 N7 90.69(10) 2_576 . ? N1 Co1 N7 91.08(10) 2_576 . ? N1 Co1 N7 88.93(10) . . ? O1 Co1 N7 90.69(10) . 2_576 ? O1 Co1 N7 89.31(10) 2_576 2_576 ? N1 Co1 N7 88.93(10) 2_576 2_576 ? N1 Co1 N7 91.07(10) . 2_576 ? N7 Co1 N7 179.999(1) . 2_576 ? N1 C1 N3 111.9(3) . . ? N1 C1 H1 124.0 . . ? N3 C1 H1 124.0 . . ? C2 N2 N3 102.3(3) . . ? N3 C3 C4 109.2(3) . . ? N3 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? N3 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.3 . . ? C9 C4 C5 118.6(4) . . ? C9 C4 C3 121.7(3) . . ? C5 C4 C3 119.4(4) . . ? C6 C5 C4 120.3(4) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 121.0(4) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C8 C7 C6 118.5(4) . . ? C8 C7 C10 120.7(4) . . ? C6 C7 C10 120.7(4) . . ? C7 C8 C9 120.7(4) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C4 C9 C8 120.7(4) . . ? C4 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? N6 C10 C7 111.1(3) . . ? N6 C10 H10A 109.4 . . ? C7 C10 H10A 109.4 . . ? N6 C10 H10B 109.4 . . ? C7 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? N4 C12 N6 111.0(4) . . ? N4 C12 H12 124.5 . . ? N6 C12 H12 124.5 . . ? C11 N5 N6 101.8(3) . . ? N7 C13 N9 110.9(3) . . ? N7 C13 H13 124.6 . . ? N9 C13 H13 124.6 . . ? C14 N8 N9 102.6(3) . . ? N9 C15 C16 114.2(3) . . ? N9 C15 H15A 108.7 . . ? C16 C15 H15A 108.7 . . ? N9 C15 H15B 108.7 . . ? C16 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C18 C16 C17 118.2(3) . . ? C18 C16 C15 120.5(3) . . ? C17 C16 C15 121.2(3) . . ? C16 C17 C18 120.6(3) . 2_466 ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 2_466 . ? C16 C18 C17 121.2(3) . 2_466 ? C16 C18 H18 119.4 . . ? C17 C18 H18 119.4 2_466 . ? N12 C19 N10 111.4(3) . . ? N12 C19 H19 124.3 . . ? N10 C19 H19 124.3 . . ? C20 N11 N12 102.3(3) . . ? N12 C21 C22 113.5(3) . . ? N12 C21 H21A 108.9 . . ? C22 C21 H21A 108.9 . . ? N12 C21 H21B 108.9 . . ? C22 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? C24 C22 C23 118.2(3) . . ? C24 C22 C21 118.3(3) . . ? C23 C22 C21 123.5(3) . . ? C24 C23 C22 121.0(3) 2_565 . ? C24 C23 H23 119.5 2_565 . ? C22 C23 H23 119.5 . . ? C23 C24 C22 120.8(3) 2_565 . ? C23 C24 H24 119.6 2_565 . ? C22 C24 H24 119.6 . . ? O5 Cl1 O3 115.0(3) . . ? O5 Cl1 O4 108.3(3) . . ? O3 Cl1 O4 106.9(4) . . ? O5 Cl1 O2 110.7(3) . . ? O3 Cl1 O2 108.1(3) . . ? O4 Cl1 O2 107.5(3) . . ? C1 N1 C2 101.7(3) . . ? C1 N1 Co1 128.6(2) . . ? C2 N1 Co1 129.7(2) . . ? N2 C2 N1 115.3(3) . . ? N2 C2 H2 122.3 . . ? N1 C2 H2 122.3 . . ? C1 N3 N2 108.8(3) . . ? C1 N3 C3 129.0(3) . . ? N2 N3 C3 122.2(3) . . ? N5 C11 N4 115.5(4) . . ? N5 C11 H11 122.2 . . ? N4 C11 H11 122.2 . . ? C12 N4 C11 102.0(3) . . ? N5 N6 C12 109.6(3) . . ? N5 N6 C10 120.1(3) . . ? C12 N6 C10 130.0(4) . . ? C13 N7 C14 102.3(3) . . ? C13 N7 Co1 126.7(2) . . ? C14 N7 Co1 130.9(2) . . ? N8 C14 N7 114.7(3) . . ? N8 C14 H14 122.7 . . ? N7 C14 H14 122.7 . . ? C13 N9 N8 109.5(3) . . ? C13 N9 C15 128.6(3) . . ? N8 N9 C15 121.7(3) . . ? C19 N10 C20 101.7(3) . . ? N11 C20 N10 115.2(3) . . ? N11 C20 H20 122.4 . . ? N10 C20 H20 122.4 . . ? C19 N12 N11 109.3(3) . . ? C19 N12 C21 129.3(3) . . ? N11 N12 C21 121.3(3) . . ? Co1 O1 H1A 118(2) . . ? Co1 O1 H1B 125(2) . . ? H1A O1 H1B 116.1(18) . . ? H6A O6 H6B 117.0(19) . . ? 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 N3 C3 C4 C9 103.3(4) . . . . ? N3 C3 C4 C5 -70.8(4) . . . . ? C9 C4 C5 C6 -2.3(6) . . . . ? C3 C4 C5 C6 171.9(3) . . . . ? C4 C5 C6 C7 -0.9(6) . . . . ? C5 C6 C7 C8 3.1(6) . . . . ? C5 C6 C7 C10 -175.1(4) . . . . ? C6 C7 C8 C9 -2.0(6) . . . . ? C10 C7 C8 C9 176.2(4) . . . . ? C5 C4 C9 C8 3.4(5) . . . . ? C3 C4 C9 C8 -170.7(3) . . . . ? C7 C8 C9 C4 -1.3(6) . . . . ? C8 C7 C10 N6 -135.3(4) . . . . ? C6 C7 C10 N6 42.8(5) . . . . ? N9 C15 C16 C18 -93.8(4) . . . . ? N9 C15 C16 C17 89.3(4) . . . . ? C18 C16 C17 C18 0.7(6) . . . 2_466 ? C15 C16 C17 C18 177.7(3) . . . 2_466 ? C17 C16 C18 C17 -0.7(6) . . . 2_466 ? C15 C16 C18 C17 -177.7(3) . . . 2_466 ? N12 C21 C22 C24 163.7(3) . . . . ? N12 C21 C22 C23 -18.1(5) . . . . ? C24 C22 C23 C24 0.0(6) . . . 2_565 ? C21 C22 C23 C24 -178.2(3) . . . 2_565 ? C23 C22 C24 C23 0.0(6) . . . 2_565 ? C21 C22 C24 C23 178.3(3) . . . 2_565 ? N3 C1 N1 C2 0.8(4) . . . . ? N3 C1 N1 Co1 -178.8(2) . . . . ? O1 Co1 N1 C1 176.9(3) . . . . ? O1 Co1 N1 C1 -3.1(3) 2_576 . . . ? N1 Co1 N1 C1 -83(45) 2_576 . . . ? N7 Co1 N1 C1 87.6(3) . . . . ? N7 Co1 N1 C1 -92.4(3) 2_576 . . . ? O1 Co1 N1 C2 -2.6(3) . . . . ? O1 Co1 N1 C2 177.4(3) 2_576 . . . ? N1 Co1 N1 C2 98(45) 2_576 . . . ? N7 Co1 N1 C2 -91.9(3) . . . . ? N7 Co1 N1 C2 88.1(3) 2_576 . . . ? N3 N2 C2 N1 0.6(5) . . . . ? C1 N1 C2 N2 -0.9(5) . . . . ? Co1 N1 C2 N2 178.7(3) . . . . ? N1 C1 N3 N2 -0.5(5) . . . . ? N1 C1 N3 C3 175.8(3) . . . . ? C2 N2 N3 C1 0.0(4) . . . . ? C2 N2 N3 C3 -176.6(3) . . . . ? C4 C3 N3 C1 -48.2(5) . . . . ? C4 C3 N3 N2 127.7(4) . . . . ? N6 N5 C11 N4 0.1(5) . . . . ? N6 C12 N4 C11 -0.2(4) . . . . ? N5 C11 N4 C12 0.1(5) . . . . ? C11 N5 N6 C12 -0.2(4) . . . . ? C11 N5 N6 C10 -175.1(3) . . . . ? N4 C12 N6 N5 0.3(5) . . . . ? N4 C12 N6 C10 174.4(4) . . . . ? C7 C10 N6 N5 65.5(5) . . . . ? C7 C10 N6 C12 -108.1(5) . . . . ? N9 C13 N7 C14 0.3(4) . . . . ? N9 C13 N7 Co1 -179.8(2) . . . . ? O1 Co1 N7 C13 40.3(3) . . . . ? O1 Co1 N7 C13 -139.7(3) 2_576 . . . ? N1 Co1 N7 C13 -49.7(3) 2_576 . . . ? N1 Co1 N7 C13 130.3(3) . . . . ? N7 Co1 N7 C13 -179(17) 2_576 . . . ? O1 Co1 N7 C14 -139.9(3) . . . . ? O1 Co1 N7 C14 40.1(3) 2_576 . . . ? N1 Co1 N7 C14 130.1(3) 2_576 . . . ? N1 Co1 N7 C14 -49.9(3) . . . . ? N7 Co1 N7 C14 0(17) 2_576 . . . ? N9 N8 C14 N7 0.4(4) . . . . ? C13 N7 C14 N8 -0.5(4) . . . . ? Co1 N7 C14 N8 179.7(2) . . . . ? N7 C13 N9 N8 -0.1(4) . . . . ? N7 C13 N9 C15 174.8(3) . . . . ? C14 N8 N9 C13 -0.2(4) . . . . ? C14 N8 N9 C15 -175.5(3) . . . . ? C16 C15 N9 C13 124.2(3) . . . . ? C16 C15 N9 N8 -61.5(4) . . . . ? N12 C19 N10 C20 0.0(4) . . . . ? N12 N11 C20 N10 0.7(5) . . . . ? C19 N10 C20 N11 -0.4(5) . . . . ? N10 C19 N12 N11 0.5(5) . . . . ? N10 C19 N12 C21 177.6(3) . . . . ? C20 N11 N12 C19 -0.7(4) . . . . ? C20 N11 N12 C21 -178.1(3) . . . . ? C22 C21 N12 C19 -68.6(5) . . . . ? C22 C21 N12 N11 108.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.593 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.053 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 776488' #TrackingRef '- crystal_data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H28 B Co0.50 F4 N12 O2' _chemical_formula_weight 632.86 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1660(18) _cell_length_b 11.812(3) _cell_length_c 15.559(4) _cell_angle_alpha 72.592(4) _cell_angle_beta 78.814(4) _cell_angle_gamma 82.024(5) _cell_volume 1399.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6324 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 27.48 _exptl_crystal_description Plate _exptl_crystal_colour Red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 653 _exptl_absorpt_coefficient_mu 0.402 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9240 _exptl_absorpt_correction_T_max 0.9802 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mini' _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10680 _diffrn_reflns_av_R_equivalents 0.0736 _diffrn_reflns_av_sigmaI/netI 0.2156 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6324 _reflns_number_gt 2652 _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^)+(0.0556P)^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 6324 _refine_ls_number_parameters 394 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1623 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1603 _refine_ls_wR_factor_gt 0.1404 _refine_ls_goodness_of_fit_ref 0.880 _refine_ls_restrained_S_all 0.880 _refine_ls_shift/su_max 0.007 _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 0.5000 0.5000 0.0000 0.0280(2) Uani 1 2 d S . . O1 O 0.4696(3) 0.5773(2) -0.13564(17) 0.0415(8) Uani 1 1 d . . . O2 O 0.3560(4) 0.7997(3) 0.8021(2) 0.0573(9) Uani 1 1 d . . . H2A H 0.4014 0.8826 0.7827 0.069 Uiso 1 1 d R . . H2B H 0.2756 0.7994 0.7658 0.069 Uiso 1 1 d R . . N1 N 0.2406(4) 0.5491(3) 0.0436(2) 0.0320(8) Uani 1 1 d . . . N2 N -0.0173(5) 0.6354(4) 0.0420(3) 0.0624(12) Uani 1 1 d . . . N3 N 0.0043(4) 0.5772(3) 0.1268(2) 0.0368(9) Uani 1 1 d . . . N4 N 0.3406(5) 0.8500(4) 0.3504(2) 0.0483(10) Uani 1 1 d . . . N5 N 0.4674(5) 0.7992(4) 0.3011(3) 0.0594(12) Uani 1 1 d . . . N6 N 0.4836(6) 0.9986(4) 0.2634(3) 0.0573(11) Uani 1 1 d . . . N7 N 0.4405(4) 0.3318(3) -0.0060(2) 0.0298(8) Uani 1 1 d . . . N8 N 0.4252(4) 0.1742(3) -0.0537(2) 0.0410(9) Uani 1 1 d . . . N9 N 0.3365(4) 0.1621(3) 0.0313(2) 0.0321(8) Uani 1 1 d . . . C1 C 0.5490(7) 0.8930(5) 0.2514(3) 0.0619(15) Uani 1 1 d . . . H1 H 0.6464 0.8857 0.2103 0.074 Uiso 1 1 calc R . . C2 C 0.3524(7) 0.9654(5) 0.3263(3) 0.0552(14) Uani 1 1 d . . . H2 H 0.2763 1.0181 0.3509 0.066 Uiso 1 1 calc R . . C3 C 0.2164(6) 0.7797(5) 0.4133(3) 0.0633(15) Uani 1 1 d . . . H3A H 0.1421 0.8283 0.4474 0.076 Uiso 1 1 calc R . . H3B H 0.2702 0.7148 0.4562 0.076 Uiso 1 1 calc R . . C4 C 0.1164(6) 0.7301(5) 0.3635(3) 0.0494(13) Uani 1 1 d . . . C5 C 0.0755(6) 0.6145(4) 0.3935(3) 0.0514(13) Uani 1 1 d . . . H5 H 0.1040 0.5663 0.4487 0.062 Uiso 1 1 calc R . . C6 C -0.0047(6) 0.5687(4) 0.3456(3) 0.0472(12) Uani 1 1 d . . . H6 H -0.0265 0.4890 0.3671 0.057 Uiso 1 1 calc R . . C7 C -0.0546(5) 0.6372(4) 0.2658(3) 0.0400(11) Uani 1 1 d . . . C8 C -0.0252(6) 0.7535(4) 0.2357(3) 0.0541(13) Uani 1 1 d . . . H8 H -0.0614 0.8018 0.1825 0.065 Uiso 1 1 calc R . . C9 C 0.0598(7) 0.8007(4) 0.2850(3) 0.0606(14) Uani 1 1 d . . . H9 H 0.0786 0.8810 0.2646 0.073 Uiso 1 1 calc R . . C10 C -0.1236(5) 0.5841(4) 0.2064(3) 0.0514(13) Uani 1 1 d . . . H10A H -0.1559 0.5050 0.2404 0.062 Uiso 1 1 calc R . . H10B H -0.2224 0.6327 0.1862 0.062 Uiso 1 1 calc R . . C11 C 0.1564(5) 0.5276(4) 0.1253(3) 0.0459(12) Uani 1 1 d . . . H11 H 0.1999 0.4819 0.1771 0.055 Uiso 1 1 calc R . . C12 C 0.1270(6) 0.6146(5) -0.0051(3) 0.0600(15) Uani 1 1 d . . . H12 H 0.1491 0.6435 -0.0683 0.072 Uiso 1 1 calc R . . C13 C 0.3504(5) 0.2572(3) 0.0576(3) 0.0323(10) Uani 1 1 d . . . H13 H 0.3020 0.2684 0.1140 0.039 Uiso 1 1 calc R . . C14 C 0.4823(5) 0.2769(4) -0.0725(3) 0.0385(11) Uani 1 1 d . . . H14 H 0.5477 0.3105 -0.1281 0.046 Uiso 1 1 calc R . . C15 C 0.2539(5) 0.0528(4) 0.0830(3) 0.0379(11) Uani 1 1 d . . . H15A H 0.3383 -0.0142 0.0914 0.045 Uiso 1 1 calc R . . H15B H 0.2025 0.0602 0.1430 0.045 Uiso 1 1 calc R . . C16 C 0.1253(5) 0.0278(3) 0.0387(3) 0.0295(10) Uani 1 1 d . . . C17 C 0.1654(5) -0.0369(4) -0.0237(3) 0.0393(11) Uani 1 1 d . . . H17 H 0.2768 -0.0620 -0.0409 0.047 Uiso 1 1 calc R . . C18 C -0.0408(6) 0.0650(4) 0.0614(3) 0.0429(12) Uani 1 1 d . . . H18 H -0.0701 0.1100 0.1029 0.051 Uiso 1 1 calc R . . N10 N 0.3724(4) 0.3259(3) 0.4375(2) 0.0407(9) Uani 1 1 d . . . N11 N 0.4524(5) 0.4074(3) 0.4576(2) 0.0536(11) Uani 1 1 d . . . N12 N 0.4517(5) 0.4555(3) 0.3072(2) 0.0510(11) Uani 1 1 d . . . C19 C 0.4963(6) 0.4830(4) 0.3776(3) 0.0517(13) Uani 1 1 d . . . H19 H 0.5529 0.5493 0.3699 0.062 Uiso 1 1 calc R . . C20 C 0.3713(6) 0.3559(4) 0.3484(3) 0.0499(13) Uani 1 1 d . . . H20 H 0.3227 0.3147 0.3188 0.060 Uiso 1 1 calc R . . C21 C 0.3083(6) 0.2237(4) 0.5066(3) 0.0446(12) Uani 1 1 d . . . H21A H 0.1938 0.2184 0.5006 0.053 Uiso 1 1 calc R . . H21B H 0.3068 0.2343 0.5662 0.053 Uiso 1 1 calc R . . C22 C 0.4103(5) 0.1092(4) 0.5007(3) 0.0369(11) Uani 1 1 d . . . C23 C 0.3426(5) 0.0051(4) 0.5461(3) 0.0414(12) Uani 1 1 d . . . H23 H 0.2340 0.0066 0.5781 0.050 Uiso 1 1 calc R . . C24 C 0.5690(6) 0.1031(4) 0.4543(3) 0.0424(12) Uani 1 1 d . . . H24 H 0.6187 0.1731 0.4222 0.051 Uiso 1 1 calc R . . F2 F 0.1413(5) 0.2560(4) 0.2538(2) 0.1195(14) Uani 1 1 d . . . F3 F -0.0299(5) 0.1177(4) 0.2827(3) 0.1249(15) Uani 1 1 d . . . F4 F -0.1342(6) 0.2847(4) 0.3030(4) 0.169(2) Uani 1 1 d . . . F5 F 0.0273(6) 0.1696(5) 0.3916(3) 0.166(2) Uani 1 1 d . . . B1 B 0.0016(8) 0.2089(7) 0.3057(4) 0.0594(18) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0325(5) 0.0292(5) 0.0218(5) -0.0054(3) -0.0040(3) -0.0055(4) O1 0.0538(19) 0.043(2) 0.0239(16) -0.0029(13) -0.0112(13) 0.0015(16) O2 0.069(2) 0.042(2) 0.056(2) 0.0008(16) -0.0229(17) -0.0039(18) N1 0.0327(19) 0.032(2) 0.030(2) -0.0055(16) -0.0072(16) -0.0025(17) N2 0.044(3) 0.082(4) 0.046(3) -0.002(2) -0.007(2) 0.010(2) N3 0.0257(19) 0.047(3) 0.035(2) -0.0100(18) -0.0021(16) -0.0004(18) N4 0.056(3) 0.056(3) 0.037(2) -0.016(2) -0.008(2) -0.013(2) N5 0.063(3) 0.057(3) 0.050(3) -0.013(2) 0.006(2) -0.004(3) N6 0.068(3) 0.058(3) 0.049(3) -0.008(2) -0.020(2) -0.016(3) N7 0.0300(19) 0.031(2) 0.031(2) -0.0095(17) -0.0056(15) -0.0082(16) N8 0.052(2) 0.040(2) 0.033(2) -0.0158(18) 0.0010(17) -0.006(2) N9 0.037(2) 0.032(2) 0.029(2) -0.0052(16) -0.0099(15) -0.0056(17) C1 0.060(3) 0.078(5) 0.044(3) -0.008(3) -0.006(3) -0.013(3) C2 0.069(4) 0.056(4) 0.051(3) -0.026(3) -0.025(3) 0.010(3) C3 0.063(3) 0.090(4) 0.038(3) -0.014(3) 0.003(3) -0.037(3) C4 0.049(3) 0.065(4) 0.029(3) -0.010(2) 0.004(2) -0.008(3) C5 0.060(3) 0.052(3) 0.031(3) 0.002(2) -0.003(2) -0.003(3) C6 0.050(3) 0.042(3) 0.044(3) -0.006(2) 0.001(2) -0.009(2) C7 0.028(2) 0.051(3) 0.038(3) -0.009(2) 0.000(2) -0.007(2) C8 0.057(3) 0.056(4) 0.042(3) 0.001(3) -0.008(2) -0.011(3) C9 0.079(4) 0.040(3) 0.055(3) -0.002(3) -0.005(3) -0.014(3) C10 0.034(3) 0.064(4) 0.049(3) -0.013(3) 0.003(2) 0.001(3) C11 0.030(3) 0.064(4) 0.037(3) -0.007(2) -0.007(2) 0.004(2) C12 0.041(3) 0.087(4) 0.037(3) 0.000(3) -0.002(2) -0.001(3) C13 0.032(2) 0.035(3) 0.033(2) -0.014(2) -0.0047(19) -0.008(2) C14 0.045(3) 0.036(3) 0.033(3) -0.006(2) 0.002(2) -0.017(2) C15 0.042(3) 0.036(3) 0.036(3) -0.002(2) -0.013(2) -0.013(2) C16 0.034(2) 0.023(3) 0.033(2) -0.0042(18) -0.0100(18) -0.008(2) C17 0.031(2) 0.044(3) 0.046(3) -0.015(2) -0.009(2) -0.004(2) C18 0.055(3) 0.040(3) 0.037(3) -0.017(2) -0.005(2) -0.006(3) N10 0.052(2) 0.041(2) 0.030(2) -0.0109(17) -0.0089(17) -0.005(2) N11 0.082(3) 0.046(3) 0.038(2) -0.014(2) -0.012(2) -0.012(2) N12 0.075(3) 0.045(3) 0.032(2) -0.0122(19) -0.003(2) -0.004(2) C19 0.072(4) 0.042(3) 0.043(3) -0.014(2) -0.002(3) -0.016(3) C20 0.065(3) 0.057(4) 0.032(3) -0.015(2) -0.011(2) -0.007(3) C21 0.052(3) 0.039(3) 0.037(3) -0.003(2) 0.002(2) -0.015(3) C22 0.041(3) 0.043(3) 0.027(2) -0.006(2) -0.0044(19) -0.014(2) C23 0.038(3) 0.048(3) 0.033(3) -0.007(2) 0.002(2) -0.010(3) C24 0.046(3) 0.043(3) 0.033(3) 0.000(2) -0.003(2) -0.017(3) F2 0.119(3) 0.168(4) 0.078(3) -0.041(2) 0.032(2) -0.087(3) F3 0.120(3) 0.135(3) 0.148(4) -0.071(3) 0.002(3) -0.067(3) F4 0.098(3) 0.093(4) 0.288(6) -0.026(4) -0.022(4) 0.007(3) F5 0.137(4) 0.301(7) 0.062(3) -0.045(3) -0.007(3) -0.045(4) B1 0.044(4) 0.078(6) 0.057(4) -0.016(4) -0.006(3) -0.015(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 Co1 O1 2.082(2) . ? Co1 O1 2.082(2) 2_665 ? Co1 N7 2.142(3) . ? Co1 N7 2.142(3) 2_665 ? Co1 N1 2.150(3) . ? Co1 N1 2.150(3) 2_665 ? O2 H2A 1.0330 . ? O2 H2B 0.9466 . ? N1 C11 1.293(5) . ? N1 C12 1.325(5) . ? N2 C12 1.295(6) . ? N2 N3 1.326(4) . ? N3 C11 1.297(5) . ? N3 C10 1.471(5) . ? N4 C2 1.313(6) . ? N4 N5 1.347(5) . ? N4 C3 1.428(5) . ? N5 C1 1.328(6) . ? N6 C2 1.318(6) . ? N6 C1 1.339(6) . ? N7 C13 1.294(4) . ? N7 C14 1.345(5) . ? N8 C14 1.291(5) . ? N8 N9 1.355(4) . ? N9 C13 1.330(4) . ? N9 C15 1.476(5) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C4 1.503(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.371(6) . ? C4 C9 1.380(6) . ? C5 C6 1.343(6) . ? C5 H5 0.9300 . ? C6 C7 1.366(6) . ? C6 H6 0.9300 . ? C7 C8 1.352(6) . ? C7 C10 1.487(6) . ? C8 C9 1.397(6) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.468(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.372(5) . ? C16 C18 1.378(5) . ? C17 C18 1.390(5) 2 ? C17 H17 0.9300 . ? C18 C17 1.390(5) 2 ? C18 H18 0.9300 . ? N10 C20 1.325(5) . ? N10 N11 1.374(5) . ? N10 C21 1.437(5) . ? N11 C19 1.314(5) . ? N12 C20 1.352(5) . ? N12 C19 1.355(5) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.505(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.354(5) . ? C22 C24 1.360(6) . ? C23 C24 1.378(6) 2_656 ? C23 H23 0.9300 . ? C24 C23 1.378(6) 2_656 ? C24 H24 0.9300 . ? F2 B1 1.347(6) . ? F3 B1 1.303(7) . ? F4 B1 1.324(7) . ? F5 B1 1.324(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O1 180.00(18) . 2_665 ? O1 Co1 N7 90.71(11) . . ? O1 Co1 N7 89.29(11) 2_665 . ? O1 Co1 N7 89.29(11) . 2_665 ? O1 Co1 N7 90.71(11) 2_665 2_665 ? N7 Co1 N7 180.00(16) . 2_665 ? O1 Co1 N1 90.14(11) . . ? O1 Co1 N1 89.86(11) 2_665 . ? N7 Co1 N1 91.09(12) . . ? N7 Co1 N1 88.91(12) 2_665 . ? O1 Co1 N1 89.86(11) . 2_665 ? O1 Co1 N1 90.14(11) 2_665 2_665 ? N7 Co1 N1 88.91(12) . 2_665 ? N7 Co1 N1 91.09(12) 2_665 2_665 ? N1 Co1 N1 180.0 . 2_665 ? H2A O2 H2B 109.9 . . ? C11 N1 C12 101.4(4) . . ? C11 N1 Co1 129.0(3) . . ? C12 N1 Co1 129.5(3) . . ? C12 N2 N3 102.7(4) . . ? C11 N3 N2 108.6(3) . . ? C11 N3 C10 128.6(4) . . ? N2 N3 C10 122.5(4) . . ? C2 N4 N5 109.1(4) . . ? C2 N4 C3 130.4(5) . . ? N5 N4 C3 120.5(4) . . ? C1 N5 N4 101.3(4) . . ? C2 N6 C1 100.2(4) . . ? C13 N7 C14 102.8(3) . . ? C13 N7 Co1 126.1(3) . . ? C14 N7 Co1 131.1(3) . . ? C14 N8 N9 102.4(3) . . ? C13 N9 N8 108.8(3) . . ? C13 N9 C15 129.4(3) . . ? N8 N9 C15 121.6(3) . . ? N5 C1 N6 116.5(5) . . ? N5 C1 H1 121.8 . . ? N6 C1 H1 121.8 . . ? N4 C2 N6 112.9(5) . . ? N4 C2 H2 123.6 . . ? N6 C2 H2 123.6 . . ? N4 C3 C4 110.5(4) . . ? N4 C3 H3A 109.6 . . ? C4 C3 H3A 109.5 . . ? N4 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C9 116.8(5) . . ? C5 C4 C3 122.4(4) . . ? C9 C4 C3 120.8(5) . . ? C6 C5 C4 122.0(4) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C7 121.2(4) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C8 C7 C6 119.1(5) . . ? C8 C7 C10 119.1(4) . . ? C6 C7 C10 121.5(4) . . ? C7 C8 C9 119.7(4) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C4 C9 C8 121.0(5) . . ? C4 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? N3 C10 C7 109.4(4) . . ? N3 C10 H10A 109.8 . . ? C7 C10 H10A 109.8 . . ? N3 C10 H10B 109.8 . . ? C7 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? N1 C11 N3 112.2(4) . . ? N1 C11 H11 123.9 . . ? N3 C11 H11 123.9 . . ? N2 C12 N1 115.0(4) . . ? N2 C12 H12 122.5 . . ? N1 C12 H12 122.5 . . ? N7 C13 N9 110.7(3) . . ? N7 C13 H13 124.6 . . ? N9 C13 H13 124.6 . . ? N8 C14 N7 115.2(4) . . ? N8 C14 H14 122.4 . . ? N7 C14 H14 122.4 . . ? C16 C15 N9 113.7(3) . . ? C16 C15 H15A 108.8 . . ? N9 C15 H15A 108.8 . . ? C16 C15 H15B 108.8 . . ? N9 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C18 118.1(4) . . ? C17 C16 C15 121.3(4) . . ? C18 C16 C15 120.6(4) . . ? C16 C17 C18 120.5(4) . 2 ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 2 . ? C16 C18 C17 121.4(4) . 2 ? C16 C18 H18 119.3 . . ? C17 C18 H18 119.3 2 . ? C20 N10 N11 109.6(4) . . ? C20 N10 C21 128.4(4) . . ? N11 N10 C21 121.9(3) . . ? C19 N11 N10 103.5(4) . . ? C20 N12 C19 103.4(4) . . ? N11 C19 N12 114.0(4) . . ? N11 C19 H19 123.0 . . ? N12 C19 H19 123.0 . . ? N10 C20 N12 109.5(4) . . ? N10 C20 H20 125.2 . . ? N12 C20 H20 125.2 . . ? N10 C21 C22 112.8(3) . . ? N10 C21 H21A 109.0 . . ? C22 C21 H21A 109.0 . . ? N10 C21 H21B 109.0 . . ? C22 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? C23 C22 C24 117.4(4) . . ? C23 C22 C21 118.5(4) . . ? C24 C22 C21 124.0(4) . . ? C22 C23 C24 121.5(4) . 2_656 ? C22 C23 H23 119.3 . . ? C24 C23 H23 119.3 2_656 . ? C22 C24 C23 121.1(4) . 2_656 ? C22 C24 H24 119.4 . . ? C23 C24 H24 119.5 2_656 . ? F3 B1 F5 107.1(6) . . ? F3 B1 F4 108.0(6) . . ? F5 B1 F4 107.7(6) . . ? F3 B1 F2 111.1(5) . . ? F5 B1 F2 108.2(5) . . ? F4 B1 F2 114.4(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 O1 Co1 N1 C11 178.0(4) . . . . ? O1 Co1 N1 C11 -2.0(4) 2_665 . . . ? N7 Co1 N1 C11 87.3(4) . . . . ? N7 Co1 N1 C11 -92.7(4) 2_665 . . . ? N1 Co1 N1 C11 -50(100) 2_665 . . . ? O1 Co1 N1 C12 -6.1(4) . . . . ? O1 Co1 N1 C12 173.9(4) 2_665 . . . ? N7 Co1 N1 C12 -96.8(4) . . . . ? N7 Co1 N1 C12 83.2(4) 2_665 . . . ? N1 Co1 N1 C12 126(100) 2_665 . . . ? C12 N2 N3 C11 0.6(6) . . . . ? C12 N2 N3 C10 174.3(4) . . . . ? C2 N4 N5 C1 1.4(5) . . . . ? C3 N4 N5 C1 178.5(4) . . . . ? O1 Co1 N7 C13 -140.3(3) . . . . ? O1 Co1 N7 C13 39.7(3) 2_665 . . . ? N7 Co1 N7 C13 77(100) 2_665 . . . ? N1 Co1 N7 C13 -50.2(3) . . . . ? N1 Co1 N7 C13 129.8(3) 2_665 . . . ? O1 Co1 N7 C14 39.4(4) . . . . ? O1 Co1 N7 C14 -140.6(4) 2_665 . . . ? N7 Co1 N7 C14 -104(100) 2_665 . . . ? N1 Co1 N7 C14 129.6(4) . . . . ? N1 Co1 N7 C14 -50.4(4) 2_665 . . . ? C14 N8 N9 C13 -1.4(4) . . . . ? C14 N8 N9 C15 -177.0(4) . . . . ? N4 N5 C1 N6 -1.3(6) . . . . ? C2 N6 C1 N5 0.6(6) . . . . ? N5 N4 C2 N6 -1.2(6) . . . . ? C3 N4 C2 N6 -178.0(4) . . . . ? C1 N6 C2 N4 0.4(5) . . . . ? C2 N4 C3 C4 111.1(5) . . . . ? N5 N4 C3 C4 -65.3(6) . . . . ? N4 C3 C4 C5 136.4(5) . . . . ? N4 C3 C4 C9 -44.2(6) . . . . ? C9 C4 C5 C6 5.0(7) . . . . ? C3 C4 C5 C6 -175.7(4) . . . . ? C4 C5 C6 C7 -2.4(7) . . . . ? C5 C6 C7 C8 -1.2(7) . . . . ? C5 C6 C7 C10 172.1(4) . . . . ? C6 C7 C8 C9 1.9(7) . . . . ? C10 C7 C8 C9 -171.5(4) . . . . ? C5 C4 C9 C8 -4.2(7) . . . . ? C3 C4 C9 C8 176.5(4) . . . . ? C7 C8 C9 C4 0.8(8) . . . . ? C11 N3 C10 C7 54.5(6) . . . . ? N2 N3 C10 C7 -117.8(5) . . . . ? C8 C7 C10 N3 69.1(5) . . . . ? C6 C7 C10 N3 -104.2(5) . . . . ? C12 N1 C11 N3 -0.8(5) . . . . ? Co1 N1 C11 N3 176.0(3) . . . . ? N2 N3 C11 N1 0.1(6) . . . . ? C10 N3 C11 N1 -173.0(4) . . . . ? N3 N2 C12 N1 -1.2(6) . . . . ? C11 N1 C12 N2 1.2(6) . . . . ? Co1 N1 C12 N2 -175.5(3) . . . . ? C14 N7 C13 N9 -0.5(4) . . . . ? Co1 N7 C13 N9 179.3(2) . . . . ? N8 N9 C13 N7 1.3(5) . . . . ? C15 N9 C13 N7 176.4(3) . . . . ? N9 N8 C14 N7 1.2(5) . . . . ? C13 N7 C14 N8 -0.5(5) . . . . ? Co1 N7 C14 N8 179.8(3) . . . . ? C13 N9 C15 C16 123.8(4) . . . . ? N8 N9 C15 C16 -61.6(5) . . . . ? N9 C15 C16 C17 87.9(5) . . . . ? N9 C15 C16 C18 -94.6(5) . . . . ? C18 C16 C17 C18 -0.9(7) . . . 2 ? C15 C16 C17 C18 176.6(3) . . . 2 ? C17 C16 C18 C17 0.9(7) . . . 2 ? C15 C16 C18 C17 -176.6(3) . . . 2 ? C20 N10 N11 C19 -0.3(5) . . . . ? C21 N10 N11 C19 177.8(4) . . . . ? N10 N11 C19 N12 -0.5(5) . . . . ? C20 N12 C19 N11 1.1(5) . . . . ? N11 N10 C20 N12 1.0(5) . . . . ? C21 N10 C20 N12 -176.9(4) . . . . ? C19 N12 C20 N10 -1.2(5) . . . . ? C20 N10 C21 C22 70.1(6) . . . . ? N11 N10 C21 C22 -107.6(4) . . . . ? N10 C21 C22 C23 -164.0(4) . . . . ? N10 C21 C22 C24 17.6(6) . . . . ? C24 C22 C23 C24 0.4(7) . . . 2_656 ? C21 C22 C23 C24 -178.1(4) . . . 2_656 ? C23 C22 C24 C23 -0.4(7) . . . 2_656 ? C21 C22 C24 C23 178.0(4) . . . 2_656 ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.507 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.070 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 776489' #TrackingRef '- crystal_data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 Co0.50 N7 O5' _chemical_formula_weight 367.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 9.0519(10) _cell_length_b 9.4026(9) _cell_length_c 10.5990(12) _cell_angle_alpha 81.697(4) _cell_angle_beta 75.627(3) _cell_angle_gamma 62.257(8) _cell_volume 772.97(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2719 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 25.01 _exptl_crystal_description Prism _exptl_crystal_colour Red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.580 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 381 _exptl_absorpt_coefficient_mu 0.635 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8836 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mini' _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6571 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2719 _reflns_number_gt 2400 _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^)+(0.0456P)^2^+0.3579P] 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 2719 _refine_ls_number_parameters 223 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1031 _refine_ls_wR_factor_gt 0.0991 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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 Co1 Co 1.0000 0.0000 0.0000 0.03055(17) Uani 1 2 d S . . O1 O 1.0585(2) -0.0033(2) 0.18040(18) 0.0470(5) Uani 1 1 d . . . H1A H 1.1497 -0.0031 0.1966 0.056 Uiso 1 1 d R . . H1B H 0.9827 -0.0109 0.2643 0.056 Uiso 1 1 d R . . N6 N 0.5593(3) 0.4004(3) 0.1781(2) 0.0367(5) Uani 1 1 d . . . N1 N 0.9347(3) -0.1936(3) 0.0757(2) 0.0352(5) Uani 1 1 d . . . N3 N 0.9619(3) -0.4159(3) 0.1839(2) 0.0369(5) Uani 1 1 d . . . N4 N 0.7459(3) 0.1841(3) 0.0746(2) 0.0358(5) Uani 1 1 d . . . N2 N 0.8337(3) -0.3768(3) 0.1207(2) 0.0461(6) Uani 1 1 d . . . C7 C 0.3565(3) 0.5372(3) 0.3783(2) 0.0335(6) Uani 1 1 d . . . C10 C 0.1206(3) 0.5451(3) 0.6083(2) 0.0339(6) Uani 1 1 d . . . C2 C 0.8235(3) -0.2435(3) 0.0572(3) 0.0410(7) Uani 1 1 d . . . H2 H 0.7458 -0.1872 0.0034 0.049 Uiso 1 1 calc R . . C5 C 0.7219(3) 0.2985(3) 0.1482(3) 0.0388(6) Uani 1 1 d . . . H5 H 0.8084 0.3057 0.1751 0.047 Uiso 1 1 calc R . . N5 N 0.4667(3) 0.3570(3) 0.1233(2) 0.0495(6) Uani 1 1 d . . . C1 C 1.0191(3) -0.3071(3) 0.1562(3) 0.0396(6) Uani 1 1 d . . . H1 H 1.1068 -0.3096 0.1887 0.047 Uiso 1 1 calc R . . C4 C 0.5853(3) 0.2264(4) 0.0625(3) 0.0426(7) Uani 1 1 d . . . H4 H 0.5604 0.1676 0.0148 0.051 Uiso 1 1 calc R . . C11 C 0.1240(4) 0.6846(3) 0.5494(3) 0.0447(7) Uani 1 1 d . . . H11 H 0.0472 0.7827 0.5871 0.054 Uiso 1 1 calc R . . C8 C 0.3568(4) 0.3963(3) 0.4385(3) 0.0441(7) Uani 1 1 d . . . H8 H 0.4367 0.2979 0.4028 0.053 Uiso 1 1 calc R . . C12 C 0.2396(4) 0.6809(3) 0.4357(3) 0.0447(7) Uani 1 1 d . . . H12 H 0.2387 0.7766 0.3971 0.054 Uiso 1 1 calc R . . C6 C 0.4803(4) 0.5430(3) 0.2554(3) 0.0434(7) Uani 1 1 d . . . H6A H 0.4207 0.6359 0.2023 0.052 Uiso 1 1 calc R . . H6B H 0.5693 0.5578 0.2785 0.052 Uiso 1 1 calc R . . C3 C 1.0154(4) -0.5573(3) 0.2709(3) 0.0427(7) Uani 1 1 d . . . H3A H 1.1172 -0.5722 0.2971 0.051 Uiso 1 1 calc R . . H3B H 1.0446 -0.6512 0.2240 0.051 Uiso 1 1 calc R . . C9 C 0.2385(4) 0.4013(3) 0.5518(3) 0.0446(7) Uani 1 1 d . . . H9 H 0.2387 0.3059 0.5903 0.053 Uiso 1 1 calc R . . N7 N 0.3936(3) 0.0031(3) 0.2769(2) 0.0392(5) Uani 1 1 d . . . O4 O 0.3949(4) -0.0177(4) 0.1656(2) 0.0898(9) Uani 1 1 d . . . O2 O 0.5148(4) -0.0120(4) 0.3118(4) 0.1119(12) Uani 1 1 d . . . O3 O 0.2551(3) 0.0416(4) 0.3521(3) 0.0962(10) Uani 1 1 d . . . O5 O 0.7991(3) 0.9931(3) 0.3714(2) 0.0697(7) Uani 1 1 d . . . H5A H 0.7263 1.0090 0.3401 0.084 Uiso 1 1 d R . . H5B H 0.7925 0.9727 0.4518 0.084 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0267(3) 0.0412(3) 0.0274(3) -0.0028(2) -0.00257(19) -0.0193(2) O1 0.0419(11) 0.0768(14) 0.0342(10) -0.0038(9) -0.0096(8) -0.0352(11) N6 0.0302(12) 0.0452(13) 0.0344(12) -0.0063(10) -0.0017(9) -0.0178(10) N1 0.0321(12) 0.0448(13) 0.0333(12) 0.0012(10) -0.0044(9) -0.0228(10) N3 0.0353(12) 0.0473(13) 0.0328(12) 0.0006(10) -0.0047(10) -0.0240(11) N4 0.0303(12) 0.0468(13) 0.0335(12) -0.0044(10) -0.0016(9) -0.0215(10) N2 0.0461(14) 0.0580(15) 0.0486(14) 0.0076(12) -0.0175(11) -0.0339(13) C7 0.0320(14) 0.0358(14) 0.0335(14) -0.0036(11) -0.0073(11) -0.0150(12) C10 0.0340(14) 0.0379(14) 0.0310(13) 0.0010(11) -0.0085(11) -0.0169(12) C2 0.0355(15) 0.0556(18) 0.0379(15) 0.0050(13) -0.0113(12) -0.0253(14) C5 0.0297(14) 0.0486(16) 0.0422(15) -0.0085(12) -0.0039(12) -0.0207(13) N5 0.0323(13) 0.0664(17) 0.0520(15) -0.0136(13) -0.0081(11) -0.0211(12) C1 0.0358(15) 0.0510(17) 0.0397(15) 0.0026(13) -0.0097(12) -0.0261(13) C4 0.0345(15) 0.0602(18) 0.0403(15) -0.0123(13) -0.0047(12) -0.0257(14) C11 0.0464(17) 0.0303(14) 0.0432(16) -0.0041(12) 0.0014(13) -0.0099(13) C8 0.0466(17) 0.0315(14) 0.0434(16) -0.0060(12) -0.0009(13) -0.0113(13) C12 0.0510(17) 0.0314(14) 0.0445(16) 0.0021(12) -0.0017(13) -0.0174(13) C6 0.0403(16) 0.0414(15) 0.0459(16) -0.0081(12) 0.0022(13) -0.0197(13) C3 0.0394(15) 0.0458(16) 0.0385(15) 0.0048(12) -0.0053(12) -0.0185(13) C9 0.0555(18) 0.0331(15) 0.0430(16) 0.0011(12) -0.0043(14) -0.0216(14) N7 0.0374(13) 0.0436(13) 0.0394(13) -0.0023(10) -0.0093(11) -0.0194(11) O4 0.113(2) 0.111(2) 0.0487(15) -0.0191(15) -0.0223(15) -0.0455(19) O2 0.088(2) 0.133(3) 0.155(3) 0.017(2) -0.082(2) -0.061(2) O3 0.0652(18) 0.109(2) 0.081(2) -0.0050(17) 0.0196(15) -0.0274(16) O5 0.0619(15) 0.117(2) 0.0461(13) -0.0025(13) -0.0063(11) -0.0557(15) _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 O1 2.0991(18) . ? Co1 O1 2.0991(18) 2_755 ? Co1 N1 2.157(2) 2_755 ? Co1 N1 2.157(2) . ? Co1 N4 2.168(2) . ? Co1 N4 2.168(2) 2_755 ? O1 H1A 0.8857 . ? O1 H1B 0.9947 . ? N6 C5 1.314(3) . ? N6 N5 1.355(3) . ? N6 C6 1.454(3) . ? N1 C1 1.324(3) . ? N1 C2 1.355(3) . ? N3 C1 1.316(3) . ? N3 N2 1.360(3) . ? N3 C3 1.456(3) . ? N4 C5 1.324(3) . ? N4 C4 1.352(3) . ? N2 C2 1.309(4) . ? C7 C12 1.379(4) . ? C7 C8 1.384(4) . ? C7 C6 1.506(4) . ? C10 C9 1.378(4) . ? C10 C11 1.380(4) . ? C10 C3 1.515(4) 2_656 ? C2 H2 0.9300 . ? C5 H5 0.9300 . ? N5 C4 1.316(4) . ? C1 H1 0.9300 . ? C4 H4 0.9300 . ? C11 C12 1.379(4) . ? C11 H11 0.9300 . ? C8 C9 1.386(4) . ? C8 H8 0.9300 . ? C12 H12 0.9300 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C3 C10 1.515(4) 2_656 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C9 H9 0.9300 . ? N7 O2 1.185(3) . ? N7 O4 1.219(3) . ? N7 O3 1.226(3) . ? O5 H5A 0.7547 . ? O5 H5B 0.8396 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O1 180.00(2) . 2_755 ? O1 Co1 N1 92.00(8) . 2_755 ? O1 Co1 N1 88.00(8) 2_755 2_755 ? O1 Co1 N1 88.00(8) . . ? O1 Co1 N1 92.00(8) 2_755 . ? N1 Co1 N1 180.00(16) 2_755 . ? O1 Co1 N4 87.64(8) . . ? O1 Co1 N4 92.36(8) 2_755 . ? N1 Co1 N4 86.75(8) 2_755 . ? N1 Co1 N4 93.25(8) . . ? O1 Co1 N4 92.36(8) . 2_755 ? O1 Co1 N4 87.64(8) 2_755 2_755 ? N1 Co1 N4 93.25(8) 2_755 2_755 ? N1 Co1 N4 86.75(8) . 2_755 ? N4 Co1 N4 180.00(10) . 2_755 ? Co1 O1 H1A 128.9 . . ? Co1 O1 H1B 121.8 . . ? H1A O1 H1B 109.3 . . ? C5 N6 N5 110.1(2) . . ? C5 N6 C6 128.1(2) . . ? N5 N6 C6 121.8(2) . . ? C1 N1 C2 102.3(2) . . ? C1 N1 Co1 121.72(17) . . ? C2 N1 Co1 135.90(18) . . ? C1 N3 N2 109.9(2) . . ? C1 N3 C3 128.5(2) . . ? N2 N3 C3 121.6(2) . . ? C5 N4 C4 102.1(2) . . ? C5 N4 Co1 121.08(17) . . ? C4 N4 Co1 136.75(18) . . ? C2 N2 N3 102.3(2) . . ? C12 C7 C8 118.5(2) . . ? C12 C7 C6 117.7(2) . . ? C8 C7 C6 123.8(2) . . ? C9 C10 C11 118.1(2) . . ? C9 C10 C3 123.2(2) . 2_656 ? C11 C10 C3 118.7(2) . 2_656 ? N2 C2 N1 114.9(2) . . ? N2 C2 H2 122.5 . . ? N1 C2 H2 122.5 . . ? N6 C5 N4 110.8(2) . . ? N6 C5 H5 124.6 . . ? N4 C5 H5 124.6 . . ? C4 N5 N6 102.0(2) . . ? N3 C1 N1 110.7(2) . . ? N3 C1 H1 124.7 . . ? N1 C1 H1 124.7 . . ? N5 C4 N4 115.0(2) . . ? N5 C4 H4 122.5 . . ? N4 C4 H4 122.5 . . ? C12 C11 C10 121.0(2) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C7 C8 C9 120.3(2) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C11 C12 C7 120.9(3) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? N6 C6 C7 114.3(2) . . ? N6 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? N6 C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? N3 C3 C10 112.9(2) . 2_656 ? N3 C3 H3A 109.0 . . ? C10 C3 H3A 109.0 2_656 . ? N3 C3 H3B 109.0 . . ? C10 C3 H3B 109.0 2_656 . ? H3A C3 H3B 107.8 . . ? C10 C9 C8 121.2(3) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? O2 N7 O4 123.8(3) . . ? O2 N7 O3 121.5(3) . . ? O4 N7 O3 114.7(3) . . ? H5A O5 H5B 120.7 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.326 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.049 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 776490' #TrackingRef '- crystal_data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 Cl Co0.50 N6' _chemical_formula_sum 'C12 H12 Cl Co0.50 N6' _chemical_formula_weight 305.19 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.4760(15) _cell_length_b 21.945(4) _cell_length_c 8.6629(17) _cell_angle_alpha 90.00 _cell_angle_beta 108.28(3) _cell_angle_gamma 90.00 _cell_volume 1349.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 626 _exptl_absorpt_coefficient_mu 0.873 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7233 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details crystalclear _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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12483 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3094 _reflns_number_gt 2618 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0249P)^2^+0.7380P] 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 3094 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.0848 _refine_ls_wR_factor_gt 0.0808 _refine_ls_goodness_of_fit_ref 1.177 _refine_ls_restrained_S_all 1.177 _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 N4 N 0.9115(3) 0.08230(8) 0.5827(2) 0.0278(4) Uani 1 1 d . . . C12 C 1.0066(3) 0.13518(11) 0.6214(3) 0.0348(6) Uani 1 1 d . . . H12 H 1.1184 0.1425 0.5989 0.042 Uiso 1 1 calc R . . N6 N 0.9302(3) 0.17553(10) 0.6933(3) 0.0387(5) Uani 1 1 d . . . N5 N 0.7732(3) 0.14601(9) 0.6991(2) 0.0300(4) Uani 1 1 d . . . C10 C 0.6515(4) 0.17180(12) 0.7860(3) 0.0433(7) Uani 1 1 d . . . H10A H 0.7240 0.1768 0.8997 0.052 Uiso 1 1 calc R . . H10B H 0.5499 0.1435 0.7800 0.052 Uiso 1 1 calc R . . Co1 Co 0.0000 0.5000 1.0000 0.02368(12) Uani 1 2 d S . . Cl1 Cl 0.33781(8) 0.47792(3) 1.16060(7) 0.03284(15) Uani 1 1 d . . . N2 N 0.1796(3) 0.42328(8) 0.6200(2) 0.0286(4) Uani 1 1 d . . . N1 N 0.0438(3) 0.45489(9) 0.7933(2) 0.0295(4) Uani 1 1 d . . . C4 C 0.4087(3) 0.34483(11) 0.6013(3) 0.0305(5) Uani 1 1 d . . . C7 C 0.5687(3) 0.23258(11) 0.7179(3) 0.0337(6) Uani 1 1 d . . . C11 C 0.7652(3) 0.09123(11) 0.6348(3) 0.0301(5) Uani 1 1 d . . . H11 H 0.6702 0.0629 0.6271 0.036 Uiso 1 1 calc R . . C2 C 0.2067(3) 0.44281(11) 0.7700(3) 0.0307(5) Uani 1 1 d . . . H2 H 0.3240 0.4474 0.8482 0.037 Uiso 1 1 calc R . . C5 C 0.5684(4) 0.34148(12) 0.7328(3) 0.0429(7) Uani 1 1 d . . . H5 H 0.6240 0.3771 0.7839 0.052 Uiso 1 1 calc R . . C8 C 0.4107(4) 0.23595(12) 0.5833(3) 0.0395(6) Uani 1 1 d . . . H8 H 0.3576 0.2004 0.5302 0.047 Uiso 1 1 calc R . . N3 N -0.0071(3) 0.42248(11) 0.5376(3) 0.0473(6) Uani 1 1 d . . . C9 C 0.3302(4) 0.29143(11) 0.5263(3) 0.0391(6) Uani 1 1 d . . . H9 H 0.2221 0.2928 0.4365 0.047 Uiso 1 1 calc R . . C3 C 0.3211(4) 0.40604(11) 0.5431(3) 0.0368(6) Uani 1 1 d . . . H3A H 0.4192 0.4368 0.5670 0.044 Uiso 1 1 calc R . . H3B H 0.2625 0.4047 0.4262 0.044 Uiso 1 1 calc R . . C6 C 0.6478(4) 0.28586(13) 0.7906(3) 0.0465(7) Uani 1 1 d . . . H6 H 0.7563 0.2845 0.8800 0.056 Uiso 1 1 calc R . . C1 C -0.0808(4) 0.44194(13) 0.6470(3) 0.0416(7) Uani 1 1 d . . . H1 H -0.2100 0.4465 0.6253 0.050 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 N4 0.0233(10) 0.0302(11) 0.0313(11) -0.0012(8) 0.0103(8) 0.0006(8) C12 0.0259(13) 0.0336(14) 0.0470(16) 0.0025(11) 0.0143(11) 0.0003(10) N6 0.0315(12) 0.0344(12) 0.0490(14) -0.0027(10) 0.0109(10) -0.0012(9) N5 0.0298(11) 0.0300(11) 0.0312(11) 0.0028(8) 0.0111(9) 0.0071(8) C10 0.0560(18) 0.0420(16) 0.0409(16) 0.0068(12) 0.0282(13) 0.0182(13) Co1 0.0221(2) 0.0263(2) 0.0254(2) -0.00113(18) 0.01142(17) -0.00013(17) Cl1 0.0233(3) 0.0428(3) 0.0331(3) 0.0017(2) 0.0099(2) 0.0029(2) N2 0.0312(11) 0.0271(11) 0.0294(11) -0.0015(8) 0.0121(9) 0.0061(8) N1 0.0286(11) 0.0300(11) 0.0319(12) -0.0045(8) 0.0124(9) 0.0010(8) C4 0.0338(13) 0.0320(13) 0.0309(14) -0.0016(10) 0.0176(10) 0.0064(10) C7 0.0372(14) 0.0360(14) 0.0335(14) 0.0006(10) 0.0190(11) 0.0113(10) C11 0.0268(12) 0.0296(13) 0.0357(14) 0.0022(10) 0.0124(10) 0.0014(9) C2 0.0270(13) 0.0367(14) 0.0282(13) -0.0049(10) 0.0085(10) 0.0039(10) C5 0.0477(17) 0.0346(15) 0.0418(16) -0.0125(12) 0.0073(13) 0.0012(12) C8 0.0361(15) 0.0304(14) 0.0507(17) -0.0077(11) 0.0118(12) -0.0045(10) N3 0.0371(13) 0.0651(16) 0.0379(14) -0.0180(11) 0.0091(10) 0.0029(11) C9 0.0319(14) 0.0377(15) 0.0430(17) -0.0033(11) 0.0049(12) 0.0031(11) C3 0.0471(16) 0.0364(14) 0.0346(15) 0.0016(11) 0.0240(12) 0.0088(11) C6 0.0463(17) 0.0475(17) 0.0361(16) -0.0079(12) -0.0010(12) 0.0104(12) C1 0.0248(13) 0.0582(18) 0.0414(16) -0.0166(13) 0.0097(11) -0.0029(11) _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 N4 C11 1.323(3) . ? N4 C12 1.347(3) . ? N4 Co1 2.1236(19) 2_646 ? C12 N6 1.312(3) . ? C12 H12 0.9300 . ? N6 N5 1.356(3) . ? N5 C11 1.319(3) . ? N5 C10 1.464(3) . ? C10 C7 1.510(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? Co1 N4 2.1236(19) 4_466 ? Co1 N4 2.1236(19) 2_656 ? Co1 N1 2.1589(19) . ? Co1 N1 2.1589(19) 3_567 ? Co1 Cl1 2.5189(10) . ? Co1 Cl1 2.5189(10) 3_567 ? N2 C2 1.323(3) . ? N2 N3 1.353(3) . ? N2 C3 1.466(3) . ? N1 C2 1.322(3) . ? N1 C1 1.347(3) . ? C4 C5 1.370(4) . ? C4 C9 1.379(3) . ? C4 C3 1.510(3) . ? C7 C6 1.371(4) . ? C7 C8 1.377(4) . ? C11 H11 0.9300 . ? C2 H2 0.9300 . ? C5 C6 1.381(4) . ? C5 H5 0.9300 . ? C8 C9 1.379(4) . ? C8 H8 0.9300 . ? N3 C1 1.308(3) . ? C9 H9 0.9300 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C6 H6 0.9300 . ? C1 H1 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 C11 N4 C12 102.46(19) . . ? C11 N4 Co1 128.28(16) . 2_646 ? C12 N4 Co1 128.38(15) . 2_646 ? N6 C12 N4 115.2(2) . . ? N6 C12 H12 122.4 . . ? N4 C12 H12 122.4 . . ? C12 N6 N5 101.9(2) . . ? C11 N5 N6 110.17(19) . . ? C11 N5 C10 128.1(2) . . ? N6 N5 C10 121.3(2) . . ? N5 C10 C7 112.7(2) . . ? N5 C10 H10A 109.1 . . ? C7 C10 H10A 109.1 . . ? N5 C10 H10B 109.1 . . ? C7 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? N4 Co1 N4 180.00(5) 4_466 2_656 ? N4 Co1 N1 91.95(7) 4_466 . ? N4 Co1 N1 88.05(7) 2_656 . ? N4 Co1 N1 88.05(7) 4_466 3_567 ? N4 Co1 N1 91.95(7) 2_656 3_567 ? N1 Co1 N1 180.000(1) . 3_567 ? N4 Co1 Cl1 90.82(5) 4_466 . ? N4 Co1 Cl1 89.18(5) 2_656 . ? N1 Co1 Cl1 89.04(6) . . ? N1 Co1 Cl1 90.96(6) 3_567 . ? N4 Co1 Cl1 89.18(5) 4_466 3_567 ? N4 Co1 Cl1 90.82(5) 2_656 3_567 ? N1 Co1 Cl1 90.96(6) . 3_567 ? N1 Co1 Cl1 89.04(6) 3_567 3_567 ? Cl1 Co1 Cl1 180.0 . 3_567 ? C2 N2 N3 109.73(19) . . ? C2 N2 C3 128.3(2) . . ? N3 N2 C3 121.9(2) . . ? C2 N1 C1 102.3(2) . . ? C2 N1 Co1 127.24(16) . . ? C1 N1 Co1 129.56(16) . . ? C5 C4 C9 118.5(2) . . ? C5 C4 C3 119.9(2) . . ? C9 C4 C3 121.5(2) . . ? C6 C7 C8 118.3(2) . . ? C6 C7 C10 120.6(2) . . ? C8 C7 C10 121.1(2) . . ? N5 C11 N4 110.3(2) . . ? N5 C11 H11 124.9 . . ? N4 C11 H11 124.9 . . ? N1 C2 N2 110.5(2) . . ? N1 C2 H2 124.7 . . ? N2 C2 H2 124.7 . . ? C4 C5 C6 120.8(2) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C8 C9 120.9(2) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C1 N3 N2 102.3(2) . . ? C4 C9 C8 120.5(2) . . ? C4 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? N2 C3 C4 112.17(19) . . ? N2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C7 C6 C5 120.9(3) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? N3 C1 N1 115.2(2) . . ? N3 C1 H1 122.4 . . ? N1 C1 H1 122.4 . . ? 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 C11 N4 C12 N6 0.2(3) . . . . ? Co1 N4 C12 N6 -169.72(17) 2_646 . . . ? N4 C12 N6 N5 -0.6(3) . . . . ? C12 N6 N5 C11 0.8(3) . . . . ? C12 N6 N5 C10 173.6(2) . . . . ? C11 N5 C10 C7 -127.6(3) . . . . ? N6 N5 C10 C7 60.9(3) . . . . ? N4 Co1 N1 C2 -109.0(2) 4_466 . . . ? N4 Co1 N1 C2 71.0(2) 2_656 . . . ? N1 Co1 N1 C2 -131(100) 3_567 . . . ? Cl1 Co1 N1 C2 -18.2(2) . . . . ? Cl1 Co1 N1 C2 161.8(2) 3_567 . . . ? N4 Co1 N1 C1 84.0(2) 4_466 . . . ? N4 Co1 N1 C1 -96.0(2) 2_656 . . . ? N1 Co1 N1 C1 62(100) 3_567 . . . ? Cl1 Co1 N1 C1 174.8(2) . . . . ? Cl1 Co1 N1 C1 -5.2(2) 3_567 . . . ? N5 C10 C7 C6 -98.8(3) . . . . ? N5 C10 C7 C8 82.2(3) . . . . ? N6 N5 C11 N4 -0.7(3) . . . . ? C10 N5 C11 N4 -172.9(2) . . . . ? C12 N4 C11 N5 0.4(3) . . . . ? Co1 N4 C11 N5 170.24(15) 2_646 . . . ? C1 N1 C2 N2 -0.7(3) . . . . ? Co1 N1 C2 N2 -170.45(15) . . . . ? N3 N2 C2 N1 0.6(3) . . . . ? C3 N2 C2 N1 178.8(2) . . . . ? C9 C4 C5 C6 -0.9(4) . . . . ? C3 C4 C5 C6 178.3(2) . . . . ? C6 C7 C8 C9 -2.2(4) . . . . ? C10 C7 C8 C9 176.8(2) . . . . ? C2 N2 N3 C1 -0.2(3) . . . . ? C3 N2 N3 C1 -178.5(2) . . . . ? C5 C4 C9 C8 0.3(4) . . . . ? C3 C4 C9 C8 -178.8(2) . . . . ? C7 C8 C9 C4 1.2(4) . . . . ? C2 N2 C3 C4 74.8(3) . . . . ? N3 N2 C3 C4 -107.2(3) . . . . ? C5 C4 C3 N2 -90.9(3) . . . . ? C9 C4 C3 N2 88.2(3) . . . . ? C8 C7 C6 C5 1.6(4) . . . . ? C10 C7 C6 C5 -177.4(3) . . . . ? C4 C5 C6 C7 -0.1(4) . . . . ? N2 N3 C1 N1 -0.3(3) . . . . ? C2 N1 C1 N3 0.6(3) . . . . ? Co1 N1 C1 N3 170.04(19) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.301 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.055 #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 776491' #TrackingRef '- crystal_data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H19 Co0.50 N3 O5' _chemical_formula_weight 410.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.6365(13) _cell_length_b 5.4996(6) _cell_length_c 24.163(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.089(7) _cell_angle_gamma 90.00 _cell_volume 1925.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Red _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 854 _exptl_absorpt_coefficient_mu 0.513 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9505 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9764 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0485 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3381 _reflns_number_gt 2815 _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^)+(0.0798P)^2^+4.1604P] 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 3381 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1528 _refine_ls_wR_factor_gt 0.1417 _refine_ls_goodness_of_fit_ref 0.928 _refine_ls_restrained_S_all 0.928 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.5000 0.5000 0.0000 0.0248(2) Uani 1 2 d S . . O2 O 0.54566(16) 0.2899(4) 0.07138(10) 0.0318(6) Uani 1 1 d . . . O3 O 0.65761(19) 0.5261(5) 0.11246(11) 0.0442(7) Uani 1 1 d . . . O1 O 0.42672(16) 0.1870(4) -0.03182(10) 0.0346(6) Uani 1 1 d . . . H1A H 0.3892 0.2488 -0.0584 0.054(14) Uiso 1 1 d R . . H1B H 0.4508 0.0378 -0.0483 0.070(15) Uiso 1 1 d R . . N1 N 0.62082(19) 0.4111(6) -0.03532(12) 0.0330(7) Uani 1 1 d . . . C9 C 0.5495(3) 0.0018(7) 0.16606(17) 0.0436(9) Uani 1 1 d . . . H9 H 0.5034 -0.0263 0.1361 0.052 Uiso 1 1 calc R . . N2 N 0.7573(2) 0.2920(6) -0.04741(14) 0.0388(8) Uani 1 1 d . . . C8 C 0.6108(2) 0.1911(7) 0.16379(14) 0.0321(8) Uani 1 1 d . . . C7 C 0.6050(2) 0.3474(6) 0.11271(14) 0.0295(8) Uani 1 1 d . . . C2 C 0.6481(3) 0.5124(10) -0.0809(2) 0.0636(14) Uani 1 1 d . . . H2 H 0.6114 0.6199 -0.1040 0.076 Uiso 1 1 calc R . . C6 C 1.0133(3) 0.2979(7) -0.03033(16) 0.0399(9) Uani 1 1 d . . . H6 H 1.0229 0.1598 -0.0510 0.048 Uiso 1 1 calc R . . C5 C 0.9131(3) 0.5572(7) 0.01117(17) 0.0410(10) Uani 1 1 d . . . H5 H 0.8546 0.5977 0.0191 0.049 Uiso 1 1 calc R . . C1 C 0.6913(2) 0.2753(7) -0.01558(17) 0.0369(9) Uani 1 1 d . . . H1 H 0.6944 0.1802 0.0165 0.044 Uiso 1 1 calc R . . C4 C 0.9247(2) 0.3509(7) -0.01992(16) 0.0354(9) Uani 1 1 d . . . C13 C 0.6770(3) 0.2327(8) 0.20962(17) 0.0479(11) Uani 1 1 d . . . H13 H 0.7182 0.3612 0.2090 0.057 Uiso 1 1 calc R . . N3 N 0.7309(3) 0.4466(9) -0.09011(17) 0.0703(13) Uani 1 1 d . . . C12 C 0.6824(3) 0.0860(10) 0.25596(19) 0.0614(13) Uani 1 1 d . . . H12 H 0.7267 0.1173 0.2867 0.074 Uiso 1 1 calc R . . C10 C 0.5566(3) -0.1466(8) 0.21290(19) 0.0564(12) Uani 1 1 d . . . H10 H 0.5157 -0.2752 0.2141 0.068 Uiso 1 1 calc R . . C11 C 0.6235(4) -0.1047(10) 0.25737(19) 0.0596(13) Uani 1 1 d . . . H11 H 0.6287 -0.2061 0.2885 0.072 Uiso 1 1 calc R . . C3 C 0.8479(3) 0.1791(8) -0.0399(2) 0.0488(11) Uani 1 1 d . . . H3A H 0.8590 0.1092 -0.0752 0.059 Uiso 1 1 calc R . . H3B H 0.8483 0.0474 -0.0132 0.059 Uiso 1 1 calc R . . O4 O 0.2047(2) 0.4851(6) 0.40683(14) 0.0674(10) Uani 1 1 d . . . O5 O 0.1875(2) 0.2111(6) 0.33879(14) 0.0623(9) Uani 1 1 d . . . H5A H 0.2365 0.1593 0.3553 0.094 Uiso 1 1 calc R . . C15 C 0.0640(3) 0.4736(7) 0.34435(16) 0.0396(9) Uani 1 1 d . . . C20 C 0.0290(4) 0.6864(8) 0.36421(19) 0.0560(12) Uani 1 1 d . . . H20 H 0.0668 0.7863 0.3887 0.067 Uiso 1 1 calc R . . C19 C -0.0620(4) 0.7491(9) 0.3475(2) 0.0691(15) Uani 1 1 d . . . H19 H -0.0858 0.8901 0.3613 0.083 Uiso 1 1 calc R . . C16 C 0.0078(3) 0.3320(8) 0.30711(17) 0.0460(10) Uani 1 1 d . . . H16 H 0.0312 0.1917 0.2928 0.055 Uiso 1 1 calc R . . C18 C -0.1177(4) 0.6036(11) 0.3106(2) 0.0693(15) Uani 1 1 d . . . H18 H -0.1789 0.6467 0.2992 0.083 Uiso 1 1 calc R . . C14 C 0.1594(3) 0.3953(8) 0.36669(17) 0.0440(10) Uani 1 1 d . . . C17 C -0.0828(3) 0.3960(10) 0.2908(2) 0.0626(13) Uani 1 1 d . . . H17 H -0.1206 0.2972 0.2660 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0220(3) 0.0228(3) 0.0289(4) 0.0014(3) 0.0013(2) -0.0006(3) O2 0.0304(13) 0.0285(12) 0.0339(13) 0.0019(11) -0.0051(11) -0.0011(11) O3 0.0429(15) 0.0383(15) 0.0463(16) 0.0081(13) -0.0115(13) -0.0120(13) O1 0.0339(14) 0.0264(13) 0.0400(14) 0.0002(11) -0.0070(12) -0.0025(11) N1 0.0251(15) 0.0385(16) 0.0355(17) 0.0059(14) 0.0043(13) 0.0036(14) C9 0.051(2) 0.042(2) 0.038(2) 0.0036(19) 0.0092(18) 0.001(2) N2 0.0263(16) 0.0460(19) 0.0448(18) 0.0055(16) 0.0074(14) 0.0092(15) C8 0.0317(19) 0.0331(19) 0.0312(19) 0.0027(16) 0.0032(15) 0.0091(17) C7 0.0275(18) 0.0254(18) 0.0343(19) -0.0007(15) 0.0002(15) 0.0040(16) C2 0.043(2) 0.096(4) 0.054(3) 0.037(3) 0.016(2) 0.027(3) C6 0.035(2) 0.040(2) 0.048(2) -0.0050(19) 0.0157(18) 0.0091(19) C5 0.0283(19) 0.044(2) 0.054(2) -0.0006(19) 0.0166(18) 0.0118(18) C1 0.031(2) 0.035(2) 0.046(2) 0.0083(17) 0.0091(17) 0.0032(17) C4 0.0285(19) 0.038(2) 0.041(2) 0.0033(17) 0.0100(16) 0.0068(17) C13 0.042(2) 0.057(3) 0.042(2) 0.011(2) -0.0029(19) -0.001(2) N3 0.045(2) 0.115(4) 0.054(2) 0.033(2) 0.0213(19) 0.028(2) C12 0.055(3) 0.085(4) 0.041(2) 0.018(2) -0.004(2) 0.010(3) C10 0.075(3) 0.046(3) 0.053(3) 0.011(2) 0.025(3) -0.004(2) C11 0.070(3) 0.068(3) 0.043(3) 0.022(2) 0.016(2) 0.021(3) C3 0.030(2) 0.046(2) 0.072(3) -0.007(2) 0.012(2) 0.010(2) O4 0.063(2) 0.077(2) 0.057(2) -0.0208(18) -0.0110(17) -0.0089(19) O5 0.0470(18) 0.072(2) 0.061(2) -0.0206(18) -0.0179(15) 0.0205(17) C15 0.048(2) 0.036(2) 0.036(2) 0.0047(17) 0.0085(18) 0.0011(19) C20 0.078(3) 0.041(2) 0.050(3) 0.003(2) 0.014(2) 0.007(3) C19 0.088(4) 0.052(3) 0.074(4) 0.015(3) 0.033(3) 0.032(3) C16 0.042(2) 0.046(2) 0.050(2) 0.001(2) 0.0054(19) 0.006(2) C18 0.052(3) 0.080(4) 0.078(4) 0.027(3) 0.016(3) 0.027(3) C14 0.046(2) 0.043(2) 0.042(2) 0.004(2) 0.003(2) -0.003(2) C17 0.043(3) 0.073(3) 0.071(3) 0.010(3) 0.001(2) 0.010(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 Co1 O2 2.105(2) 3_665 ? Co1 O2 2.105(2) . ? Co1 O1 2.115(2) . ? Co1 O1 2.115(2) 3_665 ? Co1 N1 2.126(3) . ? Co1 N1 2.126(3) 3_665 ? O2 C7 1.268(4) . ? O3 C7 1.249(4) . ? O1 H1A 0.8541 . ? O1 H1B 0.9976 . ? N1 C1 1.308(5) . ? N1 C2 1.345(5) . ? C9 C8 1.380(5) . ? C9 C10 1.388(6) . ? C9 H9 0.9300 . ? N2 C1 1.320(5) . ? N2 N3 1.351(5) . ? N2 C3 1.452(5) . ? C8 C13 1.384(5) . ? C8 C7 1.497(5) . ? C2 N3 1.314(6) . ? C2 H2 0.9300 . ? C6 C5 1.368(6) 3_765 ? C6 C4 1.386(5) . ? C6 H6 0.9300 . ? C5 C4 1.385(5) . ? C5 C6 1.368(6) 3_765 ? C5 H5 0.9300 . ? C1 H1 0.9300 . ? C4 C3 1.496(5) . ? C13 C12 1.373(6) . ? C13 H13 0.9300 . ? C12 C11 1.361(7) . ? C12 H12 0.9300 . ? C10 C11 1.367(7) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? O4 C14 1.201(5) . ? O5 C14 1.314(5) . ? O5 H5A 0.8200 . ? C15 C16 1.373(6) . ? C15 C20 1.390(6) . ? C15 C14 1.488(6) . ? C20 C19 1.381(7) . ? C20 H20 0.9300 . ? C19 C18 1.377(8) . ? C19 H19 0.9300 . ? C16 C17 1.375(6) . ? C16 H16 0.9300 . ? C18 C17 1.365(8) . ? C18 H18 0.9300 . ? C17 H17 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 O2 Co1 O2 180.00(13) 3_665 . ? O2 Co1 O1 93.59(9) 3_665 . ? O2 Co1 O1 86.41(9) . . ? O2 Co1 O1 86.41(9) 3_665 3_665 ? O2 Co1 O1 93.59(9) . 3_665 ? O1 Co1 O1 180.00(13) . 3_665 ? O2 Co1 N1 89.05(10) 3_665 . ? O2 Co1 N1 90.95(10) . . ? O1 Co1 N1 94.30(11) . . ? O1 Co1 N1 85.70(11) 3_665 . ? O2 Co1 N1 90.95(10) 3_665 3_665 ? O2 Co1 N1 89.05(10) . 3_665 ? O1 Co1 N1 85.70(11) . 3_665 ? O1 Co1 N1 94.30(11) 3_665 3_665 ? N1 Co1 N1 180.0(2) . 3_665 ? C7 O2 Co1 127.7(2) . . ? Co1 O1 H1A 100.9 . . ? Co1 O1 H1B 128.6 . . ? H1A O1 H1B 104.7 . . ? C1 N1 C2 103.1(3) . . ? C1 N1 Co1 130.0(3) . . ? C2 N1 Co1 126.4(3) . . ? C8 C9 C10 120.1(4) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C1 N2 N3 109.6(3) . . ? C1 N2 C3 128.9(3) . . ? N3 N2 C3 121.5(3) . . ? C9 C8 C13 118.6(4) . . ? C9 C8 C7 120.3(3) . . ? C13 C8 C7 121.1(3) . . ? O3 C7 O2 123.2(3) . . ? O3 C7 C8 119.5(3) . . ? O2 C7 C8 117.3(3) . . ? N3 C2 N1 114.3(4) . . ? N3 C2 H2 122.9 . . ? N1 C2 H2 122.9 . . ? C5 C6 C4 121.9(4) 3_765 . ? C5 C6 H6 119.0 3_765 . ? C4 C6 H6 119.0 . . ? C4 C5 C6 120.6(3) . 3_765 ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 3_765 . ? N1 C1 N2 110.6(3) . . ? N1 C1 H1 124.7 . . ? N2 C1 H1 124.7 . . ? C5 C4 C6 117.4(4) . . ? C5 C4 C3 123.2(3) . . ? C6 C4 C3 119.3(3) . . ? C12 C13 C8 120.6(4) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? C2 N3 N2 102.5(3) . . ? C11 C12 C13 120.6(4) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C11 C10 C9 120.3(4) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 119.7(4) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? N2 C3 C4 113.7(3) . . ? N2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? N2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C14 O5 H5A 109.5 . . ? C16 C15 C20 119.2(4) . . ? C16 C15 C14 121.3(4) . . ? C20 C15 C14 119.4(4) . . ? C15 C20 C19 119.8(5) . . ? C15 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C18 C19 C20 120.2(5) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C15 C16 C17 120.5(4) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C17 C18 C19 119.8(5) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? O4 C14 O5 123.7(4) . . ? O4 C14 C15 123.8(4) . . ? O5 C14 C15 112.5(4) . . ? C18 C17 C16 120.4(5) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.208 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.058 #===END data_6 _database_code_depnum_ccdc_archive 'CCDC 776492' #TrackingRef '- crystal_data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 Co N6 O4' _chemical_formula_weight 463.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.8872(13) _cell_length_b 10.1085(14) _cell_length_c 11.8161(14) _cell_angle_alpha 89.748(4) _cell_angle_beta 68.606(8) _cell_angle_gamma 76.373(3) _cell_volume 956.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4290 _cell_measurement_theta_min 3.64 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Red _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 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 474 _exptl_absorpt_coefficient_mu 0.940 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8342 _exptl_absorpt_correction_T_max 0.9118 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mini' _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7360 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4290 _reflns_number_gt 3810 _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^)+(0.0518P)^2^+1.3858P] 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 4290 _refine_ls_number_parameters 280 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1217 _refine_ls_wR_factor_gt 0.1177 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.116 _refine_ls_shift/su_max 0.024 _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 C20 C -0.0867(6) 1.5594(5) 0.9316(4) 0.0562(11) Uani 1 1 d . . . H20 H -0.1454 1.6008 0.8845 0.067 Uiso 1 1 calc R . . C14 C 0.9328(5) 0.9619(4) -0.0790(3) 0.0396(8) Uani 1 1 d . . . H14 H 0.8881 0.9362 -0.1329 0.047 Uiso 1 1 calc R . . Co1 Co 0.13962(5) 1.14047(4) 0.52637(4) 0.02061(13) Uani 1 1 d . . . O1 O 0.2188(3) 0.9469(2) 0.5672(2) 0.0275(5) Uani 1 1 d . . . N4 N 0.3438(3) 1.0969(2) 0.3534(2) 0.0253(5) Uani 1 1 d . . . O4 O 0.2814(3) 0.2324(2) 0.6156(2) 0.0309(5) Uani 1 1 d . . . O3 O 0.1465(3) 0.3497(2) 0.5103(2) 0.0327(5) Uani 1 1 d . . . O2 O 0.0094(3) 0.8625(2) 0.5687(2) 0.0320(5) Uani 1 1 d . . . N1 N -0.0733(4) 1.2077(3) 0.6943(3) 0.0333(6) Uani 1 1 d . . . C6 C 0.2728(4) 0.4711(3) 0.6066(3) 0.0218(6) Uani 1 1 d . . . C2 C 0.2339(3) 0.7156(3) 0.6052(2) 0.0185(5) Uani 1 1 d . . . N5 N 0.5506(3) 1.0053(3) 0.1856(3) 0.0336(6) Uani 1 1 d . . . C8 C 0.2323(4) 0.3436(3) 0.5750(3) 0.0246(6) Uani 1 1 d . . . C1 C 0.1468(3) 0.8514(3) 0.5779(2) 0.0186(5) Uani 1 1 d . . . C7 C 0.1906(4) 0.5969(3) 0.5831(3) 0.0213(6) Uani 1 1 d . . . H7 H 0.1068 0.6019 0.5527 0.026 Uiso 1 1 calc R . . C19 C -0.0456(6) 1.3939(4) 1.0654(4) 0.0540(11) Uani 1 1 d . . . H19 H -0.0752 1.3219 1.1103 0.065 Uiso 1 1 calc R . . C3 C 0.3604(4) 0.7061(3) 0.6503(3) 0.0244(6) Uani 1 1 d . . . H3 H 0.3929 0.7842 0.6623 0.029 Uiso 1 1 calc R . . C4 C 0.4385(4) 0.5806(3) 0.6776(3) 0.0267(6) Uani 1 1 d . . . H4 H 0.5204 0.5754 0.7101 0.032 Uiso 1 1 calc R . . N2 N -0.2220(5) 1.3220(4) 0.8701(3) 0.0550(7) Uani 1 1 d U . . C9 C 0.4781(4) 0.9951(3) 0.3045(3) 0.0268(6) Uani 1 1 d . . . H9 H 0.5165 0.9262 0.3470 0.032 Uiso 1 1 calc R . . C5 C 0.3940(4) 0.4638(3) 0.6561(3) 0.0263(6) Uani 1 1 d . . . H5 H 0.4455 0.3801 0.6748 0.032 Uiso 1 1 calc R . . C18 C -0.1339(5) 1.4534(5) 0.9965(3) 0.0492(10) Uani 1 1 d . . . N6 N 0.4628(4) 1.1189(3) 0.1532(3) 0.0457(8) Uani 1 1 d . . . C16 C -0.2366(5) 1.2132(5) 0.7277(4) 0.0532(11) Uani 1 1 d . . . H16 H -0.2780 1.1718 0.6793 0.064 Uiso 1 1 calc R . . C13 C 0.9179(5) 1.0002(4) 0.1241(3) 0.0385(8) Uani 1 1 d . . . H13 H 0.8632 1.0006 0.2079 0.046 Uiso 1 1 calc R . . C12 C 0.8491(4) 0.9617(4) 0.0453(3) 0.0345(7) Uani 1 1 d . . . C10 C 0.3412(4) 1.1693(4) 0.2573(3) 0.0365(8) Uani 1 1 d . . . H10 H 0.2591 1.2489 0.2646 0.044 Uiso 1 1 calc R . . C11 C 0.6923(5) 0.9096(4) 0.0931(4) 0.0446(9) Uani 1 1 d . . . H11A H 0.6611 0.8914 0.0253 0.054 Uiso 1 1 calc R . . H11B H 0.7167 0.8239 0.1280 0.054 Uiso 1 1 calc R . . N3 N -0.3333(4) 1.2815(5) 0.8339(4) 0.0680(12) Uani 1 1 d . . . C15 C -0.0698(4) 1.2769(4) 0.7871(3) 0.0408(9) Uani 1 1 d . . . H15 H 0.0263 1.2919 0.7934 0.049 Uiso 1 1 calc R . . C17 C -0.2733(6) 1.3987(5) 0.9887(4) 0.0597(8) Uani 1 1 d U . . H17A H -0.3050 1.3393 1.0533 0.072 Uiso 1 1 calc R . . H17B H -0.3697 1.4739 1.0000 0.072 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 C20 0.060(3) 0.064(3) 0.040(2) -0.003(2) -0.025(2) 0.003(2) C14 0.041(2) 0.049(2) 0.0277(17) -0.0047(15) -0.0138(15) -0.0084(16) Co1 0.0253(2) 0.01293(19) 0.0271(2) 0.00141(14) -0.01340(16) -0.00540(14) O1 0.0333(12) 0.0156(9) 0.0385(12) 0.0071(9) -0.0179(10) -0.0082(8) N4 0.0254(13) 0.0240(12) 0.0287(13) 0.0041(10) -0.0125(11) -0.0066(10) O4 0.0369(12) 0.0133(9) 0.0475(14) 0.0058(9) -0.0212(11) -0.0066(9) O3 0.0401(13) 0.0192(10) 0.0502(14) 0.0016(9) -0.0289(11) -0.0093(9) O2 0.0340(12) 0.0249(11) 0.0485(14) 0.0071(10) -0.0276(11) -0.0089(9) N1 0.0357(15) 0.0318(14) 0.0332(15) -0.0022(12) -0.0120(12) -0.0112(12) C6 0.0260(14) 0.0157(13) 0.0245(14) 0.0024(10) -0.0092(12) -0.0071(11) C2 0.0210(13) 0.0150(12) 0.0203(13) 0.0015(10) -0.0082(11) -0.0054(10) N5 0.0312(14) 0.0345(15) 0.0320(15) -0.0003(12) -0.0100(12) -0.0054(12) C8 0.0229(14) 0.0145(12) 0.0341(16) -0.0010(11) -0.0091(12) -0.0030(11) C1 0.0249(14) 0.0155(12) 0.0163(12) -0.0002(10) -0.0087(11) -0.0053(10) C7 0.0238(14) 0.0184(13) 0.0249(14) 0.0014(11) -0.0119(12) -0.0068(11) C19 0.068(3) 0.043(2) 0.042(2) -0.0010(18) -0.012(2) -0.014(2) C3 0.0282(15) 0.0195(13) 0.0309(16) 0.0014(11) -0.0150(13) -0.0100(11) C4 0.0291(15) 0.0236(14) 0.0367(17) 0.0054(12) -0.0222(14) -0.0082(12) N2 0.0516(12) 0.0639(13) 0.0519(13) -0.0098(11) -0.0182(11) -0.0203(11) C9 0.0289(15) 0.0241(14) 0.0309(16) 0.0042(12) -0.0146(13) -0.0080(12) C5 0.0279(15) 0.0201(14) 0.0326(16) 0.0059(12) -0.0143(13) -0.0042(12) C18 0.044(2) 0.061(3) 0.0332(19) -0.0233(18) -0.0037(17) -0.0107(19) N6 0.0481(19) 0.0525(19) 0.0329(16) 0.0116(14) -0.0163(15) -0.0044(15) C16 0.043(2) 0.080(3) 0.042(2) -0.008(2) -0.0103(18) -0.033(2) C13 0.042(2) 0.046(2) 0.0203(15) -0.0026(14) -0.0056(14) -0.0073(16) C12 0.0305(17) 0.0365(18) 0.0288(17) -0.0051(13) -0.0062(14) -0.0017(14) C10 0.0374(19) 0.0366(18) 0.0336(18) 0.0097(14) -0.0154(15) -0.0024(15) C11 0.0369(19) 0.046(2) 0.040(2) -0.0131(16) -0.0029(16) -0.0082(16) N3 0.0377(19) 0.112(4) 0.052(2) -0.023(2) -0.0065(17) -0.031(2) C15 0.0280(17) 0.054(2) 0.0356(19) -0.0125(16) -0.0064(15) -0.0092(16) C17 0.0567(11) 0.0644(11) 0.0567(11) -0.0059(8) -0.0182(8) -0.0179(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C20 C18 1.371(7) . ? C20 C19 1.377(7) 2_587 ? C20 H20 0.9300 . ? C14 C13 1.383(5) 2_775 ? C14 C12 1.384(5) . ? C14 H14 0.9300 . ? Co1 O2 2.030(2) 2_576 ? Co1 O1 2.036(2) . ? Co1 O3 2.136(2) 1_565 ? Co1 N4 2.143(3) . ? Co1 N1 2.155(3) . ? Co1 O4 2.257(2) 1_565 ? O1 C1 1.260(3) . ? N4 C9 1.319(4) . ? N4 C10 1.352(4) . ? O4 C8 1.266(4) . ? O4 Co1 2.257(2) 1_545 ? O3 C8 1.254(4) . ? O3 Co1 2.136(2) 1_545 ? O2 C1 1.244(3) . ? O2 Co1 2.030(2) 2_576 ? N1 C15 1.318(4) . ? N1 C16 1.345(5) . ? C6 C5 1.389(4) . ? C6 C7 1.391(4) . ? C6 C8 1.500(4) . ? C2 C3 1.394(4) . ? C2 C7 1.397(4) . ? C2 C1 1.505(4) . ? N5 C9 1.330(4) . ? N5 N6 1.366(4) . ? N5 C11 1.465(4) . ? C7 H7 0.9300 . ? C19 C18 1.372(6) . ? C19 C20 1.377(7) 2_587 ? C19 H19 0.9300 . ? C3 C4 1.393(4) . ? C3 H3 0.9300 . ? C4 C5 1.382(4) . ? C4 H4 0.9300 . ? N2 C15 1.321(5) . ? N2 N3 1.352(5) . ? N2 C17 1.466(5) . ? C9 H9 0.9300 . ? C5 H5 0.9300 . ? C18 C17 1.502(6) . ? N6 C10 1.310(5) . ? C16 N3 1.317(5) . ? C16 H16 0.9300 . ? C13 C14 1.383(5) 2_775 ? C13 C12 1.386(5) . ? C13 H13 0.9300 . ? C12 C11 1.519(5) . ? C10 H10 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C15 H15 0.9300 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? 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 C18 C20 C19 121.6(4) . 2_587 ? C18 C20 H20 119.2 . . ? C19 C20 H20 119.2 2_587 . ? C13 C14 C12 120.7(3) 2_775 . ? C13 C14 H14 119.6 2_775 . ? C12 C14 H14 119.6 . . ? O2 Co1 O1 108.67(9) 2_576 . ? O2 Co1 O3 97.08(8) 2_576 1_565 ? O1 Co1 O3 153.60(9) . 1_565 ? O2 Co1 N4 86.35(10) 2_576 . ? O1 Co1 N4 89.29(9) . . ? O3 Co1 N4 86.56(10) 1_565 . ? O2 Co1 N1 91.68(10) 2_576 . ? O1 Co1 N1 97.30(10) . . ? O3 Co1 N1 87.44(10) 1_565 . ? N4 Co1 N1 173.40(10) . . ? O2 Co1 O4 156.78(8) 2_576 1_565 ? O1 Co1 O4 94.53(8) . 1_565 ? O3 Co1 O4 59.74(8) 1_565 1_565 ? N4 Co1 O4 93.12(9) . 1_565 ? N1 Co1 O4 86.20(10) . 1_565 ? C1 O1 Co1 127.16(19) . . ? C9 N4 C10 102.9(3) . . ? C9 N4 Co1 134.3(2) . . ? C10 N4 Co1 121.9(2) . . ? C8 O4 Co1 86.81(18) . 1_545 ? C8 O3 Co1 92.63(17) . 1_545 ? C1 O2 Co1 153.6(2) . 2_576 ? C15 N1 C16 102.6(3) . . ? C15 N1 Co1 123.3(2) . . ? C16 N1 Co1 133.3(2) . . ? C5 C6 C7 120.1(3) . . ? C5 C6 C8 120.6(3) . . ? C7 C6 C8 119.4(3) . . ? C3 C2 C7 119.2(3) . . ? C3 C2 C1 120.7(2) . . ? C7 C2 C1 120.0(2) . . ? C9 N5 N6 109.6(3) . . ? C9 N5 C11 129.3(3) . . ? N6 N5 C11 120.8(3) . . ? O3 C8 O4 120.8(3) . . ? O3 C8 C6 119.1(3) . . ? O4 C8 C6 120.1(3) . . ? O2 C1 O1 124.6(3) . . ? O2 C1 C2 118.5(2) . . ? O1 C1 C2 116.9(2) . . ? C6 C7 C2 120.1(3) . . ? C6 C7 H7 120.0 . . ? C2 C7 H7 120.0 . . ? C18 C19 C20 120.1(4) . 2_587 ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 2_587 . ? C4 C3 C2 120.5(3) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 119.7(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C15 N2 N3 110.0(3) . . ? C15 N2 C17 128.2(4) . . ? N3 N2 C17 121.7(4) . . ? N4 C9 N5 110.2(3) . . ? N4 C9 H9 124.9 . . ? N5 C9 H9 124.9 . . ? C4 C5 C6 120.3(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C20 C18 C19 118.2(4) . . ? C20 C18 C17 121.5(4) . . ? C19 C18 C17 120.2(4) . . ? C10 N6 N5 102.2(3) . . ? N3 C16 N1 115.0(3) . . ? N3 C16 H16 122.5 . . ? N1 C16 H16 122.5 . . ? C14 C13 C12 120.5(3) 2_775 . ? C14 C13 H13 119.7 2_775 . ? C12 C13 H13 119.7 . . ? C14 C12 C13 118.7(3) . . ? C14 C12 C11 120.2(3) . . ? C13 C12 C11 120.9(3) . . ? N6 C10 N4 115.0(3) . . ? N6 C10 H10 122.5 . . ? N4 C10 H10 122.5 . . ? N5 C11 C12 113.4(3) . . ? N5 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? N5 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C16 N3 N2 102.0(3) . . ? N1 C15 N2 110.4(3) . . ? N1 C15 H15 124.8 . . ? N2 C15 H15 124.8 . . ? N2 C17 C18 110.8(4) . . ? N2 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 1.278 _refine_diff_density_min -1.027 _refine_diff_density_rms 0.077 #===END data_7 _database_code_depnum_ccdc_archive 'CCDC 776493' #TrackingRef '- crystal_data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H23 Co1.50 N9 O7' _chemical_formula_weight 673.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.9581(13) _cell_length_b 10.0119(12) _cell_length_c 28.536(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.002(4) _cell_angle_gamma 90.00 _cell_volume 2705.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6043 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 27.49 _exptl_crystal_description Block _exptl_crystal_colour Red _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 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1378 _exptl_absorpt_coefficient_mu 0.997 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9069 _exptl_absorpt_correction_T_max 0.9069 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mini' _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17868 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_sigmaI/netI 0.0840 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6043 _reflns_number_gt 4295 _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^)+(0.0393P)^2^+2.6498P] 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 6043 _refine_ls_number_parameters 403 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1086 _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _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 O3 O 0.3770(4) -0.6091(3) 0.93706(14) 0.0602(12) Uani 1 1 d . . . Co1 Co 0.14943(6) 0.14141(5) 0.836322(18) 0.02046(15) Uani 1 1 d . . . Co2 Co 0.5000 0.0000 1.0000 0.0248(2) Uani 1 2 d S . . O1 O 0.2830(3) -0.0003(2) 0.87830(9) 0.0282(7) Uani 1 1 d . . . C5 C 0.1784(4) -0.2342(4) 0.82192(13) 0.0189(8) Uani 1 1 d . . . H5 H 0.1602 -0.1539 0.8047 0.023 Uiso 1 1 calc R . . O2 O 0.4246(3) -0.1226(3) 0.93732(10) 0.0353(8) Uani 1 1 d . . . O5 O 0.0069(3) -0.2509(3) 0.72175(9) 0.0329(7) Uani 1 1 d . . . C3 C 0.2990(4) -0.3577(4) 0.89500(13) 0.0214(8) Uani 1 1 d . . . H3 H 0.3617 -0.3599 0.9268 0.026 Uiso 1 1 calc R . . O6 O -0.0509(3) -0.4547(3) 0.73213(9) 0.0296(7) Uani 1 1 d . . . O4 O 0.1934(3) -0.7029(3) 0.88352(9) 0.0285(7) Uani 1 1 d . . . N5 N 0.6595(4) 0.0865(3) 0.97495(13) 0.0335(9) Uani 1 1 d . . . N2 N 0.3188(4) 0.2007(3) 0.81009(12) 0.0275(8) Uani 1 1 d . . . C6 C 0.1166(4) -0.3512(4) 0.79955(13) 0.0188(8) Uani 1 1 d . . . C8 C 0.0189(4) -0.3522(4) 0.74833(14) 0.0225(9) Uani 1 1 d . . . N1 N -0.0140(4) 0.0576(3) 0.86176(12) 0.0290(8) Uani 1 1 d . . . C7 C 0.1439(4) -0.4704(4) 0.82528(13) 0.0193(8) Uani 1 1 d . . . H7 H 0.0993 -0.5483 0.8107 0.023 Uiso 1 1 calc R . . N3 N 0.4559(4) 0.3118(3) 0.77844(13) 0.0303(8) Uani 1 1 d . . . N9 N -0.1359(4) -0.0940(3) 0.88379(13) 0.0313(9) Uani 1 1 d . . . C21 C 0.4546(5) 0.1593(4) 0.82744(16) 0.0341(10) Uani 1 1 d . . . H21 H 0.4833 0.0904 0.8502 0.041 Uiso 1 1 calc R . . C4 C 0.2681(4) -0.2368(4) 0.87037(13) 0.0176(8) Uani 1 1 d . . . N6 N 0.7781(5) 0.2209(4) 0.94411(14) 0.0446(11) Uani 1 1 d . . . C22 C -0.1549(5) 0.0771(5) 0.84152(18) 0.0398(12) Uani 1 1 d . . . H22 H -0.1926 0.1478 0.8204 0.048 Uiso 1 1 calc R . . C2 C 0.2381(4) -0.4746(4) 0.87302(14) 0.0216(9) Uani 1 1 d . . . C20 C 0.3262(5) 0.2961(4) 0.77950(15) 0.0302(10) Uani 1 1 d . . . H20 H 0.2495 0.3462 0.7610 0.036 Uiso 1 1 calc R . . C11 C 0.6548(6) 0.1976(4) 0.94983(16) 0.0416(12) Uani 1 1 d . . . H11 H 0.5756 0.2516 0.9379 0.050 Uiso 1 1 calc R . . C23 C -0.0086(5) -0.0511(4) 0.88792(15) 0.0300(10) Uani 1 1 d . . . H23 H 0.0743 -0.0921 0.9068 0.036 Uiso 1 1 calc R . . N4 N 0.5428(4) 0.2244(4) 0.80954(14) 0.0396(10) Uani 1 1 d . . . C10 C 0.7957(5) 0.0475(5) 0.98405(17) 0.0389(12) Uani 1 1 d . . . H10 H 0.8316 -0.0297 1.0016 0.047 Uiso 1 1 calc R . . C1 C 0.2732(5) -0.6056(4) 0.89939(15) 0.0282(10) Uani 1 1 d . . . C19 C 0.5173(5) 0.4148(4) 0.75542(17) 0.0398(12) Uani 1 1 d . . . H19A H 0.4430 0.4609 0.7305 0.048 Uiso 1 1 calc R . . H19B H 0.5802 0.3741 0.7395 0.048 Uiso 1 1 calc R . . C9 C 0.3297(4) -0.1102(4) 0.89705(13) 0.0177(8) Uani 1 1 d . . . C24 C -0.1792(5) -0.2121(5) 0.90539(17) 0.0434(12) Uani 1 1 d . . . H24A H -0.2394 -0.1854 0.9247 0.052 Uiso 1 1 calc R . . H24B H -0.0963 -0.2555 0.9273 0.052 Uiso 1 1 calc R . . C25 C -0.2572(5) -0.3088(4) 0.86627(17) 0.0345(11) Uani 1 1 d . . . N7 N 0.8725(5) 0.1264(4) 0.96641(16) 0.0482(11) Uani 1 1 d . . . C17 C 0.5980(5) 0.5129(4) 0.79357(16) 0.0337(11) Uani 1 1 d . . . C26 C -0.1861(5) -0.3867(5) 0.84226(18) 0.0417(12) Uani 1 1 d . . . H26 H -0.0885 -0.3799 0.8503 0.050 Uiso 1 1 calc R . . C16 C 0.7416(5) 0.5248(5) 0.80613(17) 0.0392(12) Uani 1 1 d . . . H16 H 0.7912 0.4726 0.7901 0.047 Uiso 1 1 calc R . . N8 N -0.2335(4) -0.0121(4) 0.85422(16) 0.0469(11) Uani 1 1 d . . . C12 C 0.8220(7) 0.3376(5) 0.92221(19) 0.0581(16) Uani 1 1 d . . . H12A H 0.7395 0.3876 0.9034 0.070 Uiso 1 1 calc R . . H12B H 0.8730 0.3095 0.8999 0.070 Uiso 1 1 calc R . . C13 C 0.9146(6) 0.4245(5) 0.96168(18) 0.0454(13) Uani 1 1 d . . . C15 C 1.0573(7) 0.4187(5) 0.9733(2) 0.0594(17) Uani 1 1 d . . . H15 H 1.0978 0.3630 0.9553 0.071 Uiso 1 1 calc R . . C18 C 0.5282(5) 0.5924(5) 0.8177(2) 0.0492(14) Uani 1 1 d . . . H18 H 0.4304 0.5873 0.8093 0.059 Uiso 1 1 calc R . . C27 C -0.4004(6) -0.3209(5) 0.8540(2) 0.0504(14) Uani 1 1 d . . . H27 H -0.4499 -0.2699 0.8703 0.060 Uiso 1 1 calc R . . C14 C 0.8575(6) 0.5068(5) 0.9891(2) 0.0576(15) Uani 1 1 d . . . H14 H 0.7600 0.5117 0.9820 0.069 Uiso 1 1 calc R . . O7 O 0.6465(3) -0.1499(3) 1.02990(11) 0.0391(8) 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 O3 0.058(3) 0.0263(18) 0.062(2) 0.0170(17) -0.0308(19) -0.0031(16) Co1 0.0265(3) 0.0145(3) 0.0156(3) 0.0009(2) -0.0005(2) -0.0014(2) Co2 0.0344(5) 0.0147(4) 0.0176(4) 0.0016(3) -0.0033(3) -0.0022(3) O1 0.0352(18) 0.0120(14) 0.0262(15) 0.0023(12) -0.0070(13) 0.0007(12) C5 0.023(2) 0.0146(19) 0.0157(18) 0.0011(15) 0.0005(16) -0.0011(15) O2 0.047(2) 0.0193(15) 0.0229(15) -0.0013(12) -0.0142(14) 0.0011(13) O5 0.050(2) 0.0159(15) 0.0202(15) 0.0029(12) -0.0075(13) -0.0041(13) C3 0.025(2) 0.018(2) 0.0176(19) -0.0008(16) 0.0027(16) -0.0011(17) O6 0.038(2) 0.0226(15) 0.0172(14) 0.0001(12) -0.0081(13) -0.0070(13) O4 0.046(2) 0.0160(14) 0.0209(14) -0.0009(12) 0.0060(13) -0.0059(13) N5 0.040(3) 0.026(2) 0.030(2) 0.0030(16) 0.0043(18) -0.0057(17) N2 0.028(2) 0.0268(19) 0.0256(18) 0.0011(15) 0.0053(16) -0.0001(15) C6 0.019(2) 0.0167(19) 0.0183(18) -0.0028(16) 0.0017(15) -0.0008(15) C8 0.028(2) 0.018(2) 0.0192(19) -0.0010(17) 0.0036(17) 0.0001(17) N1 0.036(2) 0.0222(19) 0.0288(19) 0.0019(15) 0.0102(17) -0.0032(16) C7 0.022(2) 0.0151(19) 0.0203(19) -0.0034(15) 0.0056(16) 0.0021(15) N3 0.030(2) 0.025(2) 0.032(2) 0.0035(16) 0.0049(17) -0.0022(16) N9 0.029(2) 0.028(2) 0.037(2) 0.0008(16) 0.0097(18) -0.0070(17) C21 0.034(3) 0.029(2) 0.037(2) 0.007(2) 0.008(2) 0.001(2) C4 0.018(2) 0.0155(19) 0.0177(19) -0.0010(15) 0.0036(16) -0.0019(15) N6 0.059(3) 0.037(2) 0.038(2) 0.0019(19) 0.016(2) -0.015(2) C22 0.034(3) 0.034(3) 0.048(3) 0.006(2) 0.008(2) -0.002(2) C2 0.028(3) 0.015(2) 0.019(2) 0.0020(16) 0.0037(17) 0.0012(16) C20 0.031(3) 0.026(2) 0.029(2) 0.0025(19) 0.0035(19) -0.0006(19) C11 0.054(4) 0.028(3) 0.035(3) 0.005(2) 0.002(2) -0.007(2) C23 0.029(3) 0.031(2) 0.029(2) -0.0021(19) 0.008(2) -0.0010(19) N4 0.032(3) 0.037(2) 0.048(2) 0.0082(19) 0.0099(19) -0.0021(18) C10 0.046(3) 0.031(3) 0.038(3) 0.000(2) 0.011(2) -0.004(2) C1 0.033(3) 0.017(2) 0.026(2) 0.0011(17) -0.0030(19) 0.0003(18) C19 0.046(3) 0.034(3) 0.041(3) 0.005(2) 0.017(2) -0.010(2) C9 0.022(2) 0.016(2) 0.0142(18) 0.0000(15) 0.0032(16) -0.0013(15) C24 0.050(3) 0.041(3) 0.044(3) 0.005(2) 0.021(2) -0.014(2) C25 0.039(3) 0.027(2) 0.041(3) 0.003(2) 0.019(2) -0.008(2) N7 0.052(3) 0.040(3) 0.055(3) 0.003(2) 0.021(2) -0.005(2) C17 0.038(3) 0.029(2) 0.037(3) 0.006(2) 0.016(2) -0.006(2) C26 0.028(3) 0.050(3) 0.053(3) 0.000(2) 0.022(2) -0.006(2) C16 0.046(3) 0.038(3) 0.043(3) -0.002(2) 0.027(2) -0.006(2) N8 0.032(3) 0.045(3) 0.060(3) 0.007(2) 0.008(2) -0.006(2) C12 0.091(5) 0.040(3) 0.048(3) 0.006(3) 0.028(3) -0.023(3) C13 0.066(4) 0.034(3) 0.046(3) 0.001(2) 0.031(3) -0.017(3) C15 0.080(5) 0.046(3) 0.074(4) -0.021(3) 0.055(4) -0.015(3) C18 0.023(3) 0.048(3) 0.079(4) -0.015(3) 0.018(3) -0.005(2) C27 0.041(3) 0.040(3) 0.080(4) -0.020(3) 0.034(3) -0.006(2) C14 0.058(4) 0.047(3) 0.081(4) -0.007(3) 0.040(3) -0.010(3) O7 0.045(2) 0.0283(17) 0.0339(17) 0.0124(14) -0.0027(15) 0.0065(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C1 1.240(5) . ? Co1 O4 2.017(3) 1_565 ? Co1 O1 2.057(3) . ? Co1 O6 2.126(3) 2_556 ? Co1 N2 2.130(3) . ? Co1 N1 2.147(4) . ? Co1 O5 2.176(3) 2_556 ? Co2 O7 2.083(3) . ? Co2 O7 2.083(3) 3_657 ? Co2 O2 2.107(3) . ? Co2 O2 2.107(3) 3_657 ? Co2 N5 2.117(4) 3_657 ? Co2 N5 2.117(4) . ? O1 C9 1.249(4) . ? C5 C6 1.384(5) . ? C5 C4 1.395(5) . ? C5 H5 0.9300 . ? O2 C9 1.248(4) . ? O5 C8 1.250(4) . ? O5 Co1 2.176(3) 2_546 ? C3 C2 1.377(5) . ? C3 C4 1.386(5) . ? C3 H3 0.9300 . ? O6 C8 1.245(5) . ? O6 Co1 2.126(3) 2_546 ? O4 C1 1.251(5) . ? O4 Co1 2.017(3) 1_545 ? N5 C11 1.316(5) . ? N5 C10 1.357(6) . ? N2 C20 1.312(5) . ? N2 C21 1.353(5) . ? C6 C7 1.384(5) . ? C6 C8 1.484(5) . ? N1 C23 1.311(5) . ? N1 C22 1.357(6) . ? C7 C2 1.396(5) . ? C7 H7 0.9300 . ? N3 C20 1.310(5) . ? N3 N4 1.352(5) . ? N3 C19 1.455(5) . ? N9 C23 1.309(5) . ? N9 N8 1.350(5) . ? N9 C24 1.459(5) . ? C21 N4 1.317(5) . ? C21 H21 0.9300 . ? C4 C9 1.508(5) . ? N6 C11 1.308(6) . ? N6 N7 1.347(6) . ? N6 C12 1.454(6) . ? C22 N8 1.310(6) . ? C22 H22 0.9300 . ? C2 C1 1.498(5) . ? C20 H20 0.9300 . ? C11 H11 0.9300 . ? C23 H23 0.9300 . ? C10 N7 1.303(6) . ? C10 H10 0.9300 . ? C19 C17 1.501(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C24 C25 1.500(6) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C27 1.365(7) . ? C25 C26 1.371(6) . ? C17 C16 1.367(6) . ? C17 C18 1.375(6) . ? C26 C16 1.381(6) 1_445 ? C26 H26 0.9300 . ? C16 C26 1.381(6) 1_665 ? C16 H16 0.9300 . ? C12 C13 1.495(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C15 1.357(8) . ? C13 C14 1.374(7) . ? C15 C14 1.366(8) 3_767 ? C15 H15 0.9300 . ? C18 C27 1.368(7) 1_665 ? C18 H18 0.9300 . ? C27 C18 1.368(7) 1_445 ? C27 H27 0.9300 . ? C14 C15 1.366(8) 3_767 ? C14 H14 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 O4 Co1 O1 100.14(11) 1_565 . ? O4 Co1 O6 155.00(11) 1_565 2_556 ? O1 Co1 O6 104.78(10) . 2_556 ? O4 Co1 N2 89.28(12) 1_565 . ? O1 Co1 N2 87.54(12) . . ? O6 Co1 N2 89.65(12) 2_556 . ? O4 Co1 N1 96.14(12) 1_565 . ? O1 Co1 N1 87.41(13) . . ? O6 Co1 N1 87.19(12) 2_556 . ? N2 Co1 N1 173.17(13) . . ? O4 Co1 O5 94.72(11) 1_565 2_556 ? O1 Co1 O5 165.14(10) . 2_556 ? O6 Co1 O5 60.39(10) 2_556 2_556 ? N2 Co1 O5 92.99(12) . 2_556 ? N1 Co1 O5 90.72(13) . 2_556 ? O7 Co2 O7 180.00(16) . 3_657 ? O7 Co2 O2 87.06(11) . . ? O7 Co2 O2 92.94(11) 3_657 . ? O7 Co2 O2 92.94(11) . 3_657 ? O7 Co2 O2 87.06(11) 3_657 3_657 ? O2 Co2 O2 180.000(1) . 3_657 ? O7 Co2 N5 94.04(14) . 3_657 ? O7 Co2 N5 85.96(14) 3_657 3_657 ? O2 Co2 N5 86.61(13) . 3_657 ? O2 Co2 N5 93.39(13) 3_657 3_657 ? O7 Co2 N5 85.96(14) . . ? O7 Co2 N5 94.04(14) 3_657 . ? O2 Co2 N5 93.39(13) . . ? O2 Co2 N5 86.61(13) 3_657 . ? N5 Co2 N5 180.000(1) 3_657 . ? C9 O1 Co1 160.9(3) . . ? C6 C5 C4 119.9(3) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C9 O2 Co2 133.9(2) . . ? C8 O5 Co1 88.4(2) . 2_546 ? C2 C3 C4 120.9(3) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C8 O6 Co1 90.8(2) . 2_546 ? C1 O4 Co1 145.7(3) . 1_545 ? C11 N5 C10 102.2(4) . . ? C11 N5 Co2 128.7(4) . . ? C10 N5 Co2 128.9(3) . . ? C20 N2 C21 102.2(4) . . ? C20 N2 Co1 130.6(3) . . ? C21 N2 Co1 126.6(3) . . ? C7 C6 C5 119.9(3) . . ? C7 C6 C8 118.6(3) . . ? C5 C6 C8 121.5(3) . . ? O6 C8 O5 120.4(4) . . ? O6 C8 C6 119.5(3) . . ? O5 C8 C6 120.2(3) . . ? C23 N1 C22 102.5(4) . . ? C23 N1 Co1 127.9(3) . . ? C22 N1 Co1 126.3(3) . . ? C6 C7 C2 120.4(3) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? C20 N3 N4 110.0(3) . . ? C20 N3 C19 130.5(4) . . ? N4 N3 C19 118.8(4) . . ? C23 N9 N8 110.3(4) . . ? C23 N9 C24 129.2(4) . . ? N8 N9 C24 120.5(4) . . ? N4 C21 N2 114.7(4) . . ? N4 C21 H21 122.7 . . ? N2 C21 H21 122.7 . . ? C3 C4 C5 119.5(3) . . ? C3 C4 C9 119.1(3) . . ? C5 C4 C9 121.4(3) . . ? C11 N6 N7 111.1(4) . . ? C11 N6 C12 128.0(5) . . ? N7 N6 C12 120.6(5) . . ? N8 C22 N1 114.3(4) . . ? N8 C22 H22 122.8 . . ? N1 C22 H22 122.8 . . ? C3 C2 C7 119.2(3) . . ? C3 C2 C1 120.9(4) . . ? C7 C2 C1 119.9(3) . . ? N3 C20 N2 111.2(4) . . ? N3 C20 H20 124.4 . . ? N2 C20 H20 124.4 . . ? N6 C11 N5 110.0(5) . . ? N6 C11 H11 125.0 . . ? N5 C11 H11 125.0 . . ? N9 C23 N1 110.7(4) . . ? N9 C23 H23 124.7 . . ? N1 C23 H23 124.7 . . ? C21 N4 N3 101.9(4) . . ? N7 C10 N5 115.0(4) . . ? N7 C10 H10 122.5 . . ? N5 C10 H10 122.5 . . ? O3 C1 O4 123.9(4) . . ? O3 C1 C2 117.6(4) . . ? O4 C1 C2 118.5(4) . . ? N3 C19 C17 110.0(4) . . ? N3 C19 H19A 109.7 . . ? C17 C19 H19A 109.7 . . ? N3 C19 H19B 109.7 . . ? C17 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? O2 C9 O1 123.9(3) . . ? O2 C9 C4 117.1(3) . . ? O1 C9 C4 119.0(3) . . ? N9 C24 C25 111.2(4) . . ? N9 C24 H24A 109.4 . . ? C25 C24 H24A 109.4 . . ? N9 C24 H24B 109.4 . . ? C25 C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? C27 C25 C26 118.7(4) . . ? C27 C25 C24 120.6(4) . . ? C26 C25 C24 120.7(5) . . ? C10 N7 N6 101.6(4) . . ? C16 C17 C18 117.9(4) . . ? C16 C17 C19 122.0(4) . . ? C18 C17 C19 120.2(4) . . ? C25 C26 C16 120.5(5) . 1_445 ? C25 C26 H26 119.7 . . ? C16 C26 H26 119.7 1_445 . ? C17 C16 C26 120.9(4) . 1_665 ? C17 C16 H16 119.6 . . ? C26 C16 H16 119.6 1_665 . ? C22 N8 N9 102.1(4) . . ? N6 C12 C13 110.0(4) . . ? N6 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? N6 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C15 C13 C14 118.2(5) . . ? C15 C13 C12 120.9(5) . . ? C14 C13 C12 120.7(6) . . ? C13 C15 C14 121.2(5) . 3_767 ? C13 C15 H15 119.4 . . ? C14 C15 H15 119.4 3_767 . ? C27 C18 C17 121.4(5) 1_665 . ? C27 C18 H18 119.3 1_665 . ? C17 C18 H18 119.3 . . ? C25 C27 C18 120.6(4) . 1_445 ? C25 C27 H27 119.7 . . ? C18 C27 H27 119.7 1_445 . ? C15 C14 C13 120.6(6) 3_767 . ? C15 C14 H14 119.7 3_767 . ? C13 C14 H14 119.7 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.814 _refine_diff_density_min -0.518 _refine_diff_density_rms 0.088 #===END