# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1# _database_code_depnum_ccdc_archive 'CCDC 821493' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 Co N5 O4' _chemical_formula_weight 428.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2705(5) _cell_length_b 9.7701(5) _cell_length_c 11.4534(6) _cell_angle_alpha 72.8870(10) _cell_angle_beta 80.2130(9) _cell_angle_gamma 64.0520(10) _cell_volume 890.48(8) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3741 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 28.26 _exptl_crystal_description Block _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 442 _exptl_absorpt_coefficient_mu 1.001 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8249 _exptl_absorpt_correction_T_max 0.8249 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4606 _diffrn_reflns_av_R_equivalents 0.0103 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3101 _reflns_number_gt 2916 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0603P)^2^+0.8868P] 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 3101 _refine_ls_number_parameters 253 _refine_ls_number_restraints 631 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0950 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.1562(3) 0.2867(3) 0.2761(2) 0.0219(5) Uani 1 1 d U . . C2 C 0.2938(3) 1.1524(3) 0.3175(2) 0.0217(4) Uani 1 1 d U . . H2 H 0.3127 1.1146 0.4006 0.026 Uiso 1 1 calc R . . C3 C 0.4022(3) 1.0755(3) 0.2337(2) 0.0225(4) Uani 1 1 d U . . C4 C 0.3746(3) 1.1323(3) 0.1095(2) 0.0237(5) Uani 1 1 d U . . H4 H 0.4477 1.0805 0.0539 0.028 Uiso 1 1 calc R . . C5 C 0.2381(3) 1.2664(3) 0.06848(19) 0.0234(4) Uani 1 1 d U . . C7 C 1.0419(3) 0.3766(3) 0.36503(19) 0.0211(4) Uani 1 1 d U . . C8 C 0.5512(3) 0.9314(3) 0.2778(2) 0.0258(5) Uani 1 1 d U . . C9 C 0.6891(3) 0.4500(3) 0.5692(2) 0.0341(5) Uani 1 1 d U . . C6 C 0.1285(3) 1.3432(3) 0.1519(2) 0.0245(5) Uani 1 1 d U . . H6 H 0.0365 1.4325 0.1246 0.029 Uiso 1 1 calc R . . H9 H 0.7758 0.3653 0.5469 0.029 Uiso 1 1 d R . . C10 C 0.5736(3) 0.4377(3) 0.6564(2) 0.0373(6) Uani 1 1 d U . . H10 H 0.5668 0.3456 0.7047 0.045 Uiso 1 1 calc R . . C11 C 0.5235(3) 0.6853(3) 0.5751(2) 0.0315(5) Uani 1 1 d U . . H11 H 0.4737 0.7943 0.5589 0.038 Uiso 1 1 calc R . . C12 C 0.3307(3) 0.6326(4) 0.7461(3) 0.0430(6) Uani 1 1 d U . . H12A H 0.3067 0.5420 0.7857 0.052 Uiso 1 1 calc R . . H12B H 0.2376 0.7135 0.7020 0.052 Uiso 1 1 calc R . . C13 C 0.3624(4) 0.6918(4) 0.8408(3) 0.0481(7) Uani 1 1 d U . . H13A H 0.3681 0.7920 0.8022 0.058 Uiso 1 1 calc R . . H13B H 0.4660 0.6188 0.8740 0.058 Uiso 1 1 calc R . . C14 C 0.2348(3) 0.7124(4) 0.9456(3) 0.0431(7) Uani 1 1 d U . . H14A H 0.1290 0.7633 0.9126 0.052 Uiso 1 1 calc R . . H14B H 0.2474 0.6100 0.9978 0.052 Uiso 1 1 calc R . . C15 C 1.2483(4) 0.8082(4) 0.0192(3) 0.0477(7) Uani 1 1 d U . . H15A H 1.3557 0.7581 0.0493 0.057 Uiso 1 1 calc R . . H15B H 1.2345 0.9105 -0.0337 0.057 Uiso 1 1 calc R . . C16 C 1.0349(3) 0.7554(3) 0.1710(2) 0.0324(5) Uani 1 1 d U . . H16 H 1.0291 0.6810 0.1389 0.039 Uiso 1 1 calc R . . C17 C 0.9957(3) 0.9079(3) 0.2843(2) 0.0373(6) Uani 1 1 d U . . H17 H 0.9559 0.9599 0.3468 0.045 Uiso 1 1 calc R . . C18 C 1.1070(4) 0.9280(3) 0.1968(3) 0.0411(6) Uani 1 1 d U . . H18 H 1.1573 0.9948 0.1878 0.049 Uiso 1 1 calc R . . Co1 Co 0.80389(3) 0.69759(3) 0.38927(2) 0.02080(13) Uani 1 1 d U . . N1 N 0.6574(2) 0.6057(2) 0.51803(18) 0.0277(4) Uani 1 1 d U . . N2 N 0.4690(3) 0.5883(3) 0.65912(19) 0.0332(5) Uani 1 1 d U . . N3 N 1.1314(3) 0.8305(3) 0.1239(2) 0.0339(5) Uani 1 1 d U . . N4 N 0.9498(2) 0.7999(2) 0.26768(18) 0.0279(4) Uani 1 1 d U . . O1 O 0.92669(19) 0.50310(18) 0.32100(14) 0.0267(4) Uani 1 1 d U . . O2 O 0.93319(19) 0.6804(2) 0.52332(14) 0.0283(4) Uani 1 1 d U . . O3 O 0.6105(2) 0.8241(2) 0.22160(18) 0.0400(5) Uani 1 1 d U . . O4 O 0.61212(19) 0.9217(2) 0.37155(15) 0.0334(4) Uani 1 1 d U . . N5 N 0.2069(2) 1.3282(2) -0.05292(15) 0.0242(4) Uani 1 1 d U . . H5A H 0.2694 1.2600 -0.0871 0.029 Uiso 1 1 d R . . H5B H 0.2086 1.4153 -0.0683 0.029 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 C1 0.0192(11) 0.0226(11) 0.0213(11) -0.0087(9) 0.0007(8) -0.0045(9) C2 0.0195(10) 0.0198(10) 0.0201(10) -0.0063(8) 0.0002(8) -0.0025(9) C3 0.0194(10) 0.0190(10) 0.0270(11) -0.0078(9) 0.0000(9) -0.0052(9) C4 0.0211(11) 0.0233(11) 0.0240(11) -0.0124(9) 0.0054(9) -0.0051(9) C5 0.0264(11) 0.0243(11) 0.0154(8) -0.0062(8) -0.0021(8) -0.0056(9) C7 0.0179(10) 0.0231(10) 0.0202(10) -0.0089(8) 0.0019(8) -0.0055(9) C8 0.0184(10) 0.0215(11) 0.0282(11) -0.0051(9) 0.0069(9) -0.0034(9) C9 0.0307(12) 0.0324(12) 0.0337(12) -0.0085(10) 0.0023(10) -0.0092(10) C6 0.0218(11) 0.0216(11) 0.0227(11) -0.0084(9) -0.0028(9) 0.0001(9) C10 0.0391(14) 0.0394(14) 0.0327(13) -0.0064(11) 0.0040(11) -0.0193(12) C11 0.0310(12) 0.0340(12) 0.0297(12) -0.0129(10) 0.0083(10) -0.0138(10) C12 0.0358(14) 0.0593(16) 0.0377(14) -0.0205(12) 0.0168(11) -0.0243(12) C13 0.0417(15) 0.0713(19) 0.0406(15) -0.0270(14) 0.0180(12) -0.0306(14) C14 0.0398(15) 0.0588(18) 0.0352(14) -0.0184(13) 0.0155(12) -0.0261(14) C15 0.0457(16) 0.0658(18) 0.0401(15) -0.0217(13) 0.0206(12) -0.0331(14) C16 0.0332(12) 0.0419(13) 0.0277(12) -0.0150(10) 0.0087(10) -0.0199(11) C17 0.0437(14) 0.0355(13) 0.0341(13) -0.0162(10) 0.0087(11) -0.0165(11) C18 0.0476(15) 0.0418(14) 0.0434(15) -0.0175(12) 0.0098(12) -0.0268(12) Co1 0.01710(18) 0.02072(19) 0.01760(18) -0.00732(12) 0.00266(12) -0.00115(13) N1 0.0255(10) 0.0309(10) 0.0248(9) -0.0102(8) 0.0051(8) -0.0100(8) N2 0.0324(11) 0.0446(12) 0.0286(10) -0.0161(9) 0.0112(9) -0.0214(10) N3 0.0332(11) 0.0429(12) 0.0299(11) -0.0134(9) 0.0106(9) -0.0209(10) N4 0.0259(10) 0.0311(10) 0.0232(9) -0.0082(8) 0.0037(8) -0.0094(8) O1 0.0228(8) 0.0237(8) 0.0234(8) -0.0104(6) 0.0009(6) 0.0019(6) O2 0.0236(8) 0.0361(9) 0.0189(8) -0.0087(7) 0.0000(6) -0.0057(7) O3 0.0352(10) 0.0246(9) 0.0465(11) -0.0155(8) 0.0085(8) 0.0005(8) O4 0.0222(8) 0.0329(9) 0.0294(9) -0.0049(7) -0.0022(7) 0.0012(7) N5 0.0273(10) 0.0206(9) 0.0104(8) -0.0054(7) -0.0048(7) 0.0054(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.390(3) 1_645 ? C1 C2 1.396(3) 1_645 ? C1 C7 1.509(3) . ? C2 C3 1.390(3) . ? C2 C1 1.396(3) 1_465 ? C2 H2 0.9300 . ? C3 C4 1.389(3) . ? C3 C8 1.504(3) . ? C4 C5 1.388(3) . ? C4 H4 0.9300 . ? C5 N5 1.368(3) . ? C5 C6 1.390(3) . ? C7 O2 1.252(3) 2_766 ? C7 O1 1.259(3) . ? C8 O4 1.257(3) . ? C8 O3 1.260(3) . ? C9 C10 1.355(4) . ? C9 N1 1.374(3) . ? C9 H9 0.9318 . ? C6 C1 1.390(3) 1_465 ? C6 H6 0.9300 . ? C10 N2 1.369(4) . ? C10 H10 0.9300 . ? C11 N1 1.323(3) . ? C11 N2 1.340(3) . ? C11 H11 0.9300 . ? C12 N2 1.469(3) . ? C12 C13 1.491(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.527(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.485(4) 1_456 ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N3 1.471(3) . ? C15 C14 1.485(4) 1_654 ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N4 1.313(3) . ? C16 N3 1.344(3) . ? C16 H16 0.9300 . ? C17 C18 1.348(4) . ? C17 N4 1.367(3) . ? C17 H17 0.9300 . ? C18 N3 1.368(3) . ? C18 H18 0.9300 . ? Co1 O2 2.0296(16) . ? Co1 O1 2.0487(15) . ? Co1 N1 2.1054(19) . ? Co1 O4 2.1096(17) . ? Co1 N4 2.120(2) . ? O2 C7 1.252(3) 2_766 ? N5 H5A 0.8195 . ? N5 H5B 0.8235 . ? 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 C6 C1 C2 120.2(2) 1_645 1_645 ? C6 C1 C7 119.62(19) 1_645 . ? C2 C1 C7 120.12(19) 1_645 . ? C3 C2 C1 119.5(2) . 1_465 ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 1_465 . ? C4 C3 C2 120.3(2) . . ? C4 C3 C8 120.0(2) . . ? C2 C3 C8 119.7(2) . . ? C5 C4 C3 120.1(2) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? N5 C5 C4 122.2(2) . . ? N5 C5 C6 117.9(2) . . ? C4 C5 C6 119.9(2) . . ? O2 C7 O1 124.8(2) 2_766 . ? O2 C7 C1 118.08(19) 2_766 . ? O1 C7 C1 117.14(19) . . ? O4 C8 O3 121.9(2) . . ? O4 C8 C3 118.2(2) . . ? O3 C8 C3 119.9(2) . . ? C10 C9 N1 109.6(2) . . ? C10 C9 H9 124.9 . . ? N1 C9 H9 125.5 . . ? C1 C6 C5 120.1(2) 1_465 . ? C1 C6 H6 120.0 1_465 . ? C5 C6 H6 120.0 . . ? C9 C10 N2 106.1(2) . . ? C9 C10 H10 126.9 . . ? N2 C10 H10 126.9 . . ? N1 C11 N2 111.2(2) . . ? N1 C11 H11 124.4 . . ? N2 C11 H11 124.4 . . ? N2 C12 C13 111.6(2) . . ? N2 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? N2 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C12 C13 C14 113.5(2) . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C15 C14 C13 111.1(2) 1_456 . ? C15 C14 H14A 109.4 1_456 . ? C13 C14 H14A 109.4 . . ? C15 C14 H14B 109.4 1_456 . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? N3 C15 C14 114.4(2) . 1_654 ? N3 C15 H15A 108.7 . . ? C14 C15 H15A 108.7 1_654 . ? N3 C15 H15B 108.7 . . ? C14 C15 H15B 108.7 1_654 . ? H15A C15 H15B 107.6 . . ? N4 C16 N3 111.8(2) . . ? N4 C16 H16 124.1 . . ? N3 C16 H16 124.1 . . ? C18 C17 N4 109.9(2) . . ? C18 C17 H17 125.1 . . ? N4 C17 H17 125.1 . . ? C17 C18 N3 106.4(2) . . ? C17 C18 H18 126.8 . . ? N3 C18 H18 126.8 . . ? O2 Co1 O1 107.91(6) . . ? O2 Co1 N1 91.56(7) . . ? O1 Co1 N1 96.17(7) . . ? O2 Co1 O4 104.03(7) . . ? O1 Co1 O4 147.62(7) . . ? N1 Co1 O4 88.04(7) . . ? O2 Co1 N4 85.60(7) . . ? O1 Co1 N4 87.34(7) . . ? N1 Co1 N4 176.04(7) . . ? O4 Co1 N4 89.97(7) . . ? C11 N1 C9 105.6(2) . . ? C11 N1 Co1 127.08(17) . . ? C9 N1 Co1 127.06(16) . . ? C11 N2 C10 107.5(2) . . ? C11 N2 C12 126.9(2) . . ? C10 N2 C12 125.5(2) . . ? C16 N3 C18 106.5(2) . . ? C16 N3 C15 127.9(2) . . ? C18 N3 C15 125.5(2) . . ? C16 N4 C17 105.3(2) . . ? C16 N4 Co1 126.94(17) . . ? C17 N4 Co1 126.95(16) . . ? C7 O1 Co1 129.05(14) . . ? C7 O2 Co1 143.05(16) 2_766 . ? C8 O4 Co1 100.01(14) . . ? C5 N5 H5A 105.4 . . ? C5 N5 H5B 104.2 . . ? H5A N5 H5B 122.2 . . ? 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 C1 C2 C3 C4 0.4(3) 1_465 . . . ? C1 C2 C3 C8 179.5(2) 1_465 . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C8 C3 C4 C5 -179.2(2) . . . . ? C3 C4 C5 N5 179.0(2) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C6 C1 C7 O2 177.4(2) 1_645 . . 2_766 ? C2 C1 C7 O2 -6.2(3) 1_645 . . 2_766 ? C6 C1 C7 O1 -1.7(3) 1_645 . . . ? C2 C1 C7 O1 174.8(2) 1_645 . . . ? C4 C3 C8 O4 148.1(2) . . . . ? C2 C3 C8 O4 -31.0(3) . . . . ? C4 C3 C8 O3 -32.6(3) . . . . ? C2 C3 C8 O3 148.3(2) . . . . ? N5 C5 C6 C1 -178.9(2) . . . 1_465 ? C4 C5 C6 C1 0.6(4) . . . 1_465 ? N1 C9 C10 N2 -0.1(3) . . . . ? N2 C12 C13 C14 -170.0(3) . . . . ? C12 C13 C14 C15 -165.5(3) . . . 1_456 ? N4 C17 C18 N3 0.0(3) . . . . ? N2 C11 N1 C9 -0.1(3) . . . . ? N2 C11 N1 Co1 -174.32(16) . . . . ? C10 C9 N1 C11 0.1(3) . . . . ? C10 C9 N1 Co1 174.30(17) . . . . ? O2 Co1 N1 C11 88.5(2) . . . . ? O1 Co1 N1 C11 -163.3(2) . . . . ? O4 Co1 N1 C11 -15.5(2) . . . . ? O2 Co1 N1 C9 -84.5(2) . . . . ? O1 Co1 N1 C9 23.7(2) . . . . ? O4 Co1 N1 C9 171.6(2) . . . . ? N1 C11 N2 C10 0.1(3) . . . . ? N1 C11 N2 C12 175.3(2) . . . . ? C9 C10 N2 C11 0.0(3) . . . . ? C9 C10 N2 C12 -175.4(2) . . . . ? C13 C12 N2 C11 -69.2(4) . . . . ? C13 C12 N2 C10 105.2(3) . . . . ? N4 C16 N3 C18 0.8(3) . . . . ? N4 C16 N3 C15 177.5(3) . . . . ? C17 C18 N3 C16 -0.4(3) . . . . ? C17 C18 N3 C15 -177.2(3) . . . . ? C14 C15 N3 C16 11.8(5) 1_654 . . . ? C14 C15 N3 C18 -172.1(3) 1_654 . . . ? N3 C16 N4 C17 -0.7(3) . . . . ? N3 C16 N4 Co1 -171.17(17) . . . . ? C18 C17 N4 C16 0.5(3) . . . . ? C18 C17 N4 Co1 170.88(19) . . . . ? O2 Co1 N4 C16 126.1(2) . . . . ? O1 Co1 N4 C16 17.9(2) . . . . ? O4 Co1 N4 C16 -129.8(2) . . . . ? O2 Co1 N4 C17 -42.3(2) . . . . ? O1 Co1 N4 C17 -150.5(2) . . . . ? O4 Co1 N4 C17 61.8(2) . . . . ? O2 C7 O1 Co1 28.3(3) 2_766 . . . ? C1 C7 O1 Co1 -152.71(15) . . . . ? O2 Co1 O1 C7 14.3(2) . . . . ? N1 Co1 O1 C7 -79.34(19) . . . . ? O4 Co1 O1 C7 -175.44(17) . . . . ? N4 Co1 O1 C7 98.82(19) . . . . ? O1 Co1 O2 C7 -85.6(2) . . . 2_766 ? N1 Co1 O2 C7 11.3(3) . . . 2_766 ? O4 Co1 O2 C7 99.7(2) . . . 2_766 ? N4 Co1 O2 C7 -171.4(3) . . . 2_766 ? O3 C8 O4 Co1 -1.5(3) . . . . ? C3 C8 O4 Co1 177.77(16) . . . . ? O2 Co1 O4 C8 171.78(14) . . . . ? O1 Co1 O4 C8 1.3(2) . . . . ? N1 Co1 O4 C8 -97.10(15) . . . . ? N4 Co1 O4 C8 86.33(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5A O3 0.82 1.91 2.681(2) 156.3 2_675 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.871 _refine_diff_density_min -0.676 _refine_diff_density_rms 0.064 data_2# _database_code_depnum_ccdc_archive 'CCDC 821494' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H12 Co N3 O4' _chemical_formula_weight 333.19 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' 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 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 11.0663(5) _cell_length_b 7.6170(3) _cell_length_c 16.0392(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.7540(10) _cell_angle_gamma 90.00 _cell_volume 1351.34(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5235 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 27.91 _exptl_crystal_description Block _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.638 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 1.289 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7825 _exptl_absorpt_correction_T_max 0.7825 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6460 _diffrn_reflns_av_R_equivalents 0.0148 _diffrn_reflns_av_sigmaI/netI 0.0139 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2361 _reflns_number_gt 2127 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0566P)^2^+1.2514P] 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 2361 _refine_ls_number_parameters 190 _refine_ls_number_restraints 120 _refine_ls_R_factor_all 0.0328 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0892 _refine_ls_wR_factor_gt 0.0857 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6761(2) 0.2692(3) 0.14128(13) 0.0240(5) Uani 1 1 d U . . C2 C 0.64808(19) 0.4443(3) 0.10377(13) 0.0208(4) Uani 1 1 d U . . C3 C 0.60578(19) 0.5800(3) 0.15289(13) 0.0217(4) Uani 1 1 d U . . H3 H 0.5979 0.5634 0.2099 0.026 Uiso 1 1 calc R . . C4 C 0.57538(19) 0.7402(3) 0.11687(12) 0.0203(4) Uani 1 1 d U . . C5 C 0.59102(19) 0.7679(3) 0.03277(13) 0.0220(4) Uani 1 1 d U . . H5 H 0.5726 0.8766 0.0092 0.026 Uiso 1 1 calc R . . C6 C 0.63449(19) 0.6327(3) -0.01672(13) 0.0206(4) Uani 1 1 d U . . C7 C 0.66151(19) 0.4708(3) 0.01877(14) 0.0212(5) Uani 1 1 d U . . H7 H 0.6887 0.3797 -0.0144 0.025 Uiso 1 1 calc R . . C8 C 0.64650(19) 0.6608(3) -0.10918(13) 0.0234(5) Uani 1 1 d U . . C9 C 0.8812(3) -0.2928(4) 0.24186(17) 0.0475(7) Uani 1 1 d U . . H9 H 0.8559 -0.3329 0.2932 0.057 Uiso 1 1 calc R . . C10 C 0.9721(3) -0.3614(5) 0.1985(2) 0.0672(10) Uani 1 1 d U . . H10 H 1.0210 -0.4557 0.2143 0.081 Uiso 1 1 calc R . . C11 C 0.8926(2) -0.1444(4) 0.12907(16) 0.0413(6) Uani 1 1 d U . . H11 H 0.8771 -0.0626 0.0870 0.050 Uiso 1 1 calc R . . C12 C 1.0637(3) -0.2942(7) 0.0595(2) 0.0795(12) Uani 1 1 d U . . H12A H 1.1358 -0.3512 0.0823 0.095 Uiso 1 1 calc R . . H12B H 1.0875 -0.1811 0.0375 0.095 Uiso 1 1 calc R . . C13 C 1.0111(4) -0.4052(6) -0.0112(2) 0.0806(14) Uani 1 1 d U . . H13A H 0.9352 -0.3533 -0.0305 0.097 Uiso 1 1 calc R . . H13B H 1.0659 -0.4016 -0.0573 0.097 Uiso 1 1 calc R . . Co1 Co 0.68702(3) -0.01034(4) 0.229913(17) 0.02218(13) Uani 1 1 d . . . N1 N 0.83221(18) -0.1547(3) 0.19821(12) 0.0300(4) Uani 1 1 d U . . N2 N 0.9786(2) -0.2660(4) 0.12700(15) 0.0575(7) Uani 1 1 d U . . N3 N 0.53466(17) 0.8789(2) 0.17004(11) 0.0231(4) Uani 1 1 d U . . H3A H 0.5196 0.9812 0.1496 0.028 Uiso 1 1 calc R . . H3B H 0.5254 0.8595 0.2223 0.028 Uiso 1 1 calc R . . O1 O 0.70788(17) 0.1446(2) 0.09723(11) 0.0365(4) Uani 1 1 d U . . O2 O 0.66469(15) 0.2492(2) 0.22009(9) 0.0291(4) Uani 1 1 d U . . O3 O 0.68916(17) 0.5301(2) -0.14869(10) 0.0307(4) Uani 1 1 d U . . O4 O 0.61592(17) 0.8009(2) -0.14168(10) 0.0381(4) Uani 1 1 d U . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0285(11) 0.0190(11) 0.0247(11) 0.0022(9) 0.0041(9) 0.0006(9) C2 0.0250(10) 0.0174(10) 0.0201(10) 0.0010(8) 0.0023(8) -0.0008(8) C3 0.0304(11) 0.0184(11) 0.0167(10) 0.0002(8) 0.0048(8) -0.0024(9) C4 0.0261(11) 0.0169(10) 0.0182(10) -0.0035(8) 0.0028(8) -0.0003(8) C5 0.0293(11) 0.0173(10) 0.0195(10) 0.0021(8) 0.0014(8) 0.0012(9) C6 0.0248(10) 0.0207(11) 0.0165(10) -0.0007(8) 0.0021(8) -0.0006(8) C7 0.0235(11) 0.0181(10) 0.0221(11) -0.0031(8) 0.0042(8) 0.0012(8) C8 0.0270(11) 0.0251(11) 0.0182(10) -0.0006(9) 0.0013(8) -0.0005(9) C9 0.0585(17) 0.0498(17) 0.0344(14) 0.0063(12) 0.0019(12) 0.0236(14) C10 0.073(2) 0.080(2) 0.0482(18) 0.0097(16) 0.0039(15) 0.0504(19) C11 0.0407(15) 0.0477(16) 0.0359(14) 0.0037(12) 0.0086(11) 0.0123(12) C12 0.060(2) 0.118(3) 0.062(2) 0.004(2) 0.0285(17) 0.043(2) C13 0.073(2) 0.123(4) 0.0475(19) 0.010(2) 0.0247(17) 0.057(3) Co1 0.0340(2) 0.01678(19) 0.0159(2) 0.00050(10) 0.00363(13) 0.00370(11) N1 0.0335(11) 0.0297(11) 0.0268(10) -0.0013(8) 0.0020(8) 0.0050(8) N2 0.0471(14) 0.0810(19) 0.0450(14) 0.0053(13) 0.0137(11) 0.0345(13) N3 0.0377(11) 0.0159(9) 0.0161(8) -0.0009(7) 0.0059(7) 0.0041(7) O1 0.0572(11) 0.0195(8) 0.0332(9) 0.0013(7) 0.0107(8) 0.0105(8) O2 0.0457(10) 0.0200(8) 0.0217(8) 0.0047(6) 0.0038(7) 0.0031(7) O3 0.0470(10) 0.0289(9) 0.0164(8) -0.0034(6) 0.0055(7) 0.0075(7) O4 0.0648(12) 0.0289(9) 0.0209(8) 0.0072(7) 0.0069(8) 0.0125(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.241(3) . ? C1 O2 1.283(3) . ? C1 C2 1.492(3) . ? C2 C3 1.390(3) . ? C2 C7 1.391(3) . ? C3 C4 1.387(3) . ? C3 H3 0.9300 . ? C4 C5 1.382(3) . ? C4 N3 1.439(3) . ? C5 C6 1.395(3) . ? C5 H5 0.9300 . ? C6 C7 1.387(3) . ? C6 C8 1.508(3) . ? C7 H7 0.9300 . ? C8 O4 1.230(3) . ? C8 O3 1.279(3) . ? C9 C10 1.346(4) . ? C9 N1 1.366(3) . ? C9 H9 0.9300 . ? C10 N2 1.361(4) . ? C10 H10 0.9300 . ? C11 N1 1.314(3) . ? C11 N2 1.329(4) . ? C11 H11 0.9300 . ? C12 N2 1.473(4) . ? C12 C13 1.517(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C13 1.511(10) 3_745 ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? Co1 O3 1.9524(16) 4_566 ? Co1 O2 1.9978(16) . ? Co1 N1 2.0249(19) . ? Co1 N3 2.0923(19) 1_545 ? N3 Co1 2.0923(19) 1_565 ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? O3 Co1 1.9524(16) 4_565 ? 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 C1 O2 120.5(2) . . ? O1 C1 C2 120.87(19) . . ? O2 C1 C2 118.57(19) . . ? C3 C2 C7 119.7(2) . . ? C3 C2 C1 120.38(19) . . ? C7 C2 C1 119.89(19) . . ? C4 C3 C2 120.00(19) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.34(19) . . ? C5 C4 N3 121.15(19) . . ? C3 C4 N3 118.40(18) . . ? C4 C5 C6 119.89(19) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 119.79(19) . . ? C7 C6 C8 120.37(19) . . ? C5 C6 C8 119.79(19) . . ? C6 C7 C2 120.2(2) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? O4 C8 O3 124.5(2) . . ? O4 C8 C6 120.56(19) . . ? O3 C8 C6 114.93(19) . . ? C10 C9 N1 108.9(3) . . ? C10 C9 H9 125.5 . . ? N1 C9 H9 125.5 . . ? C9 C10 N2 106.7(3) . . ? C9 C10 H10 126.6 . . ? N2 C10 H10 126.6 . . ? N1 C11 N2 111.2(2) . . ? N1 C11 H11 124.4 . . ? N2 C11 H11 124.4 . . ? N2 C12 C13 113.1(3) . . ? N2 C12 H12A 109.0 . . ? C13 C12 H12A 109.0 . . ? N2 C12 H12B 109.0 . . ? C13 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C13 C13 C12 114.6(4) 3_745 . ? C13 C13 H13A 108.6 3_745 . ? C12 C13 H13A 108.6 . . ? C13 C13 H13B 108.6 3_745 . ? C12 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? O3 Co1 O2 98.78(7) 4_566 . ? O3 Co1 N1 102.89(8) 4_566 . ? O2 Co1 N1 127.94(8) . . ? O3 Co1 N3 114.31(7) 4_566 1_545 ? O2 Co1 N3 105.47(7) . 1_545 ? N1 Co1 N3 107.47(7) . 1_545 ? C11 N1 C9 105.9(2) . . ? C11 N1 Co1 127.37(17) . . ? C9 N1 Co1 126.50(17) . . ? C11 N2 C10 107.1(2) . . ? C11 N2 C12 126.5(3) . . ? C10 N2 C12 126.4(3) . . ? C4 N3 Co1 107.79(13) . 1_565 ? C4 N3 H3A 120.0 . . ? Co1 N3 H3A 87.3 1_565 . ? C4 N3 H3B 120.0 . . ? Co1 N3 H3B 75.0 1_565 . ? H3A N3 H3B 120.0 . . ? C1 O2 Co1 100.35(13) . . ? C8 O3 Co1 124.11(15) . 4_565 ? 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 C1 C2 C3 176.3(2) . . . . ? O2 C1 C2 C3 -2.7(3) . . . . ? O1 C1 C2 C7 -2.2(3) . . . . ? O2 C1 C2 C7 178.9(2) . . . . ? C7 C2 C3 C4 1.0(3) . . . . ? C1 C2 C3 C4 -177.41(19) . . . . ? C2 C3 C4 C5 -2.3(3) . . . . ? C2 C3 C4 N3 -178.54(19) . . . . ? C3 C4 C5 C6 1.8(3) . . . . ? N3 C4 C5 C6 177.84(19) . . . . ? C4 C5 C6 C7 0.2(3) . . . . ? C4 C5 C6 C8 177.42(19) . . . . ? C5 C6 C7 C2 -1.5(3) . . . . ? C8 C6 C7 C2 -178.74(19) . . . . ? C3 C2 C7 C6 0.9(3) . . . . ? C1 C2 C7 C6 179.34(19) . . . . ? C7 C6 C8 O4 175.7(2) . . . . ? C5 C6 C8 O4 -1.5(3) . . . . ? C7 C6 C8 O3 -4.0(3) . . . . ? C5 C6 C8 O3 178.8(2) . . . . ? N1 C9 C10 N2 -0.6(4) . . . . ? N2 C12 C13 C13 -68.1(5) . . . 3_745 ? N2 C11 N1 C9 -1.1(3) . . . . ? N2 C11 N1 Co1 -176.4(2) . . . . ? C10 C9 N1 C11 1.0(4) . . . . ? C10 C9 N1 Co1 176.3(2) . . . . ? O3 Co1 N1 C11 -158.3(2) 4_566 . . . ? O2 Co1 N1 C11 -46.1(3) . . . . ? N3 Co1 N1 C11 80.7(2) 1_545 . . . ? O3 Co1 N1 C9 27.4(2) 4_566 . . . ? O2 Co1 N1 C9 139.6(2) . . . . ? N3 Co1 N1 C9 -93.6(2) 1_545 . . . ? N1 C11 N2 C10 0.8(4) . . . . ? N1 C11 N2 C12 179.9(3) . . . . ? C9 C10 N2 C11 -0.1(4) . . . . ? C9 C10 N2 C12 -179.2(4) . . . . ? C13 C12 N2 C11 -83.4(5) . . . . ? C13 C12 N2 C10 95.5(4) . . . . ? C5 C4 N3 Co1 -97.4(2) . . . 1_565 ? C3 C4 N3 Co1 78.7(2) . . . 1_565 ? O1 C1 O2 Co1 -7.5(2) . . . . ? C2 C1 O2 Co1 171.37(16) . . . . ? O3 Co1 O2 C1 173.32(14) 4_566 . . . ? N1 Co1 O2 C1 59.32(16) . . . . ? N3 Co1 O2 C1 -68.32(14) 1_545 . . . ? O4 C8 O3 Co1 -11.6(3) . . . 4_565 ? C6 C8 O3 Co1 168.05(14) . . . 4_565 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3B O2 0.86 2.47 3.031(2) 123.5 2_655 N3 H3A O4 0.86 2.24 2.981(2) 144.6 3_675 N3 H3A O1 0.86 2.59 3.045(3) 114.3 1_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.911 _refine_diff_density_min -0.531 _refine_diff_density_rms 0.061 data_3# _database_code_depnum_ccdc_archive 'CCDC 821495' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H21 Co N5 O5' _chemical_formula_weight 494.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.195(2) _cell_length_b 10.242(5) _cell_length_c 12.011(2) _cell_angle_alpha 100.37(4) _cell_angle_beta 95.68(3) _cell_angle_gamma 115.82(2) _cell_volume 1088.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 2680 _cell_measurement_theta_min 1.7592 _cell_measurement_theta_max 25.9748 _exptl_crystal_description Block _exptl_crystal_colour Purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.509 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 510 _exptl_absorpt_coefficient_mu 0.834 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8509 _exptl_absorpt_correction_T_max 0.8509 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8687 _diffrn_reflns_av_R_equivalents 0.0686 _diffrn_reflns_av_sigmaI/netI 0.1278 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.94 _reflns_number_total 4219 _reflns_number_gt 2265 _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^)+(0.1056P)^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 SHELXL _refine_ls_extinction_coef 0.034(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4219 _refine_ls_number_parameters 299 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1126 _refine_ls_R_factor_gt 0.0742 _refine_ls_wR_factor_ref 0.2094 _refine_ls_wR_factor_gt 0.1900 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9535(7) 0.8001(7) 0.6013(6) 0.0387(15) Uani 1 1 d . . . H1 H 1.0373 0.8781 0.5850 0.046 Uiso 1 1 calc R . . C2 C 0.8080(7) 0.6493(7) 0.6936(7) 0.0500(18) Uani 1 1 d . . . H2 H 0.7694 0.5996 0.7513 0.060 Uiso 1 1 calc R . . C3 C 0.7364(7) 0.6184(6) 0.5834(6) 0.0422(16) Uani 1 1 d . . . H3 H 0.6369 0.5435 0.5518 0.051 Uiso 1 1 calc R . . C4 C 1.0695(7) 0.8390(8) 0.8067(6) 0.0575(19) Uani 1 1 d . . . H4A H 1.1598 0.9109 0.7854 0.069 Uiso 1 1 calc R . . H4B H 1.0914 0.7623 0.8315 0.069 Uiso 1 1 calc R . . C5 C 1.0313(7) 0.9215(7) 0.9068(6) 0.0446(16) Uani 1 1 d . . . C6 C 1.0006(9) 1.0372(9) 0.8963(7) 0.065(2) Uani 1 1 d . . . H6 H 1.0017 1.0653 0.8250 0.078 Uiso 1 1 calc R . . C7 C 1.0323(9) 0.8855(9) 1.0110(7) 0.064(2) Uani 1 1 d . . . H7 H 1.0555 0.8074 1.0207 0.077 Uiso 1 1 calc R . . C8 C 0.5942(8) 0.4628(7) 0.1642(7) 0.0553(18) Uani 1 1 d . . . H8 H 0.5138 0.4359 0.2039 0.066 Uiso 1 1 calc R . . C9 C 0.7164(13) 0.4645(9) 0.0276(8) 0.108(4) Uani 1 1 d . . . H9 H 0.7422 0.4444 -0.0451 0.129 Uiso 1 1 calc R . . C10 C 0.8072(11) 0.5691(9) 0.1230(8) 0.099(4) Uani 1 1 d . . . H10 H 0.9103 0.6327 0.1301 0.119 Uiso 1 1 calc R . . C11 C 0.4537(10) 0.2563(8) -0.0184(8) 0.085(3) Uani 1 1 d . . . H11A H 0.4418 0.2626 -0.0997 0.102 Uiso 1 1 calc R . . H11B H 0.3622 0.2458 0.0093 0.102 Uiso 1 1 calc R . . C12 C 0.4770(8) 0.1227(7) -0.0107(6) 0.0544(19) Uani 1 1 d . . . C13 C 0.4099(9) 0.0380(8) 0.0625(7) 0.065(2) Uani 1 1 d . . . H13 H 0.3475 0.0627 0.1062 0.078 Uiso 1 1 calc R . . C14 C 0.5680(9) 0.0836(8) -0.0736(7) 0.064(2) Uani 1 1 d . . . H14 H 0.6155 0.1413 -0.1248 0.077 Uiso 1 1 calc R . . C15 C 0.5981(6) 0.8049(6) 0.3535(5) 0.0326(13) Uani 1 1 d . . . C16 C 0.5004(6) 0.8792(6) 0.3555(5) 0.0305(13) Uani 1 1 d . . . C17 C 0.3510(6) 0.7980(6) 0.3560(5) 0.0322(13) Uani 1 1 d . . . H17 H 0.3104 0.6953 0.3565 0.039 Uiso 1 1 calc R . . C18 C 0.2593(6) 0.8685(6) 0.3556(5) 0.0309(13) Uani 1 1 d . . . C19 C 0.3188(6) 1.0168(6) 0.3550(5) 0.0327(13) Uani 1 1 d . . . H19 H 0.2567 1.0641 0.3544 0.039 Uiso 1 1 calc R . . C20 C 0.4696(6) 1.0991(6) 0.3552(5) 0.0368(14) Uani 1 1 d . . . C21 C 0.5594(6) 1.0303(6) 0.3576(5) 0.0335(14) Uani 1 1 d . . . H21 H 0.6629 1.0869 0.3608 0.040 Uiso 1 1 calc R . . C22 C 0.0979(6) 0.7808(6) 0.3601(5) 0.0359(14) Uani 1 1 d . . . Co1 Co 0.80421(8) 0.72985(8) 0.36132(7) 0.0325(3) Uani 1 1 d . . . N1 N 0.8272(5) 0.7098(5) 0.5247(4) 0.0326(11) Uani 1 1 d . . . N2 N 0.9472(5) 0.7666(6) 0.7055(5) 0.0429(13) Uani 1 1 d . . . N3 N 0.5842(8) 0.3946(6) 0.0537(5) 0.0622(17) Uani 1 1 d . . . N4 N 0.7279(6) 0.5697(5) 0.2088(5) 0.0452(14) Uani 1 1 d . . . N5 N 0.5313(4) 1.2572(4) 0.3548(4) 0.0217(9) Uani 1 1 d U . . H5C H 0.6268 1.3096 0.3561 0.026 Uiso 1 1 calc R . . H5D H 0.4730 1.3001 0.3532 0.026 Uiso 1 1 calc R . . O1 O 0.5497(4) 0.6721(4) 0.3574(4) 0.0444(11) Uani 1 1 d . . . O2 O 0.7344(4) 0.8827(4) 0.3477(4) 0.0380(10) Uani 1 1 d . . . O3 O 0.0514(5) 0.6503(5) 0.3748(5) 0.0566(14) Uani 1 1 d . . . O4 O 0.0163(4) 0.8447(4) 0.3504(4) 0.0384(10) Uani 1 1 d . . . O5 O 0.8265(5) 0.3760(5) 0.4002(5) 0.0663(15) Uani 1 1 d . . . H5A H 0.8789 0.4511 0.3742 0.080 Uiso 1 1 d R . . H5B H 0.8776 0.3549 0.4477 0.080 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 C1 0.037(3) 0.041(3) 0.044(4) 0.011(3) 0.015(3) 0.022(3) C2 0.042(4) 0.050(4) 0.055(5) 0.019(3) 0.017(4) 0.015(3) C3 0.033(3) 0.035(3) 0.053(5) 0.010(3) 0.014(3) 0.010(3) C4 0.045(4) 0.081(5) 0.040(5) 0.005(4) 0.006(4) 0.028(4) C5 0.040(4) 0.059(4) 0.029(4) 0.007(3) 0.006(3) 0.020(3) C6 0.093(6) 0.081(5) 0.033(5) 0.025(4) 0.016(4) 0.046(5) C7 0.083(6) 0.074(5) 0.046(5) 0.022(4) 0.016(4) 0.042(5) C8 0.057(5) 0.045(4) 0.059(5) 0.005(4) -0.001(4) 0.024(4) C9 0.150(10) 0.065(5) 0.060(7) -0.007(5) 0.054(7) 0.009(6) C10 0.101(7) 0.059(5) 0.076(7) -0.012(4) 0.049(6) -0.012(5) C11 0.099(7) 0.058(5) 0.071(6) -0.009(4) -0.041(5) 0.036(5) C12 0.063(5) 0.032(3) 0.049(5) -0.005(3) -0.018(4) 0.016(3) C13 0.065(5) 0.056(4) 0.062(6) -0.006(4) 0.012(4) 0.024(4) C14 0.083(6) 0.051(4) 0.050(5) 0.009(4) 0.008(4) 0.026(4) C15 0.027(3) 0.037(3) 0.038(4) 0.014(3) 0.012(3) 0.016(2) C16 0.027(3) 0.040(3) 0.033(3) 0.010(3) 0.010(3) 0.022(3) C17 0.022(3) 0.034(3) 0.042(4) 0.010(3) 0.009(3) 0.013(2) C18 0.024(3) 0.036(3) 0.039(4) 0.012(3) 0.009(3) 0.018(2) C19 0.026(3) 0.040(3) 0.040(4) 0.013(3) 0.007(3) 0.020(3) C20 0.031(3) 0.034(3) 0.047(4) 0.006(3) 0.009(3) 0.018(3) C21 0.021(3) 0.028(3) 0.050(4) 0.007(3) 0.009(3) 0.010(2) C22 0.027(3) 0.040(3) 0.045(4) 0.014(3) 0.010(3) 0.016(3) Co1 0.0251(5) 0.0337(5) 0.0404(6) 0.0071(4) 0.0076(4) 0.0158(3) N1 0.023(2) 0.030(2) 0.046(3) 0.008(2) 0.007(2) 0.014(2) N2 0.040(3) 0.053(3) 0.034(3) 0.005(3) 0.009(3) 0.022(3) N3 0.090(5) 0.038(3) 0.048(4) -0.002(3) -0.006(4) 0.028(3) N4 0.045(3) 0.036(3) 0.047(4) 0.002(2) 0.011(3) 0.014(2) N5 0.0208(12) 0.0222(12) 0.0257(13) 0.0046(9) 0.0041(9) 0.0139(9) O1 0.032(2) 0.035(2) 0.074(3) 0.020(2) 0.019(2) 0.0182(18) O2 0.022(2) 0.038(2) 0.058(3) 0.014(2) 0.013(2) 0.0158(17) O3 0.036(2) 0.046(3) 0.096(4) 0.030(3) 0.025(3) 0.020(2) O4 0.030(2) 0.044(2) 0.052(3) 0.016(2) 0.013(2) 0.0249(19) O5 0.044(3) 0.045(3) 0.102(5) 0.022(3) 0.011(3) 0.013(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.335(7) . ? C1 N2 1.356(7) . ? C1 H1 0.9500 . ? C2 C3 1.357(9) . ? C2 N2 1.375(7) . ? C2 H2 0.9500 . ? C3 N1 1.357(6) . ? C3 H3 0.9500 . ? C4 N2 1.467(8) . ? C4 C5 1.525(9) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C7 1.367(9) . ? C5 C6 1.373(9) . ? C6 C7 1.402(10) 2_777 ? C6 H6 0.9500 . ? C7 C6 1.402(10) 2_777 ? C7 H7 0.9500 . ? C8 N4 1.299(8) . ? C8 N3 1.356(9) . ? C8 H8 0.9500 . ? C9 N3 1.323(11) . ? C9 C10 1.343(12) . ? C9 H9 0.9500 . ? C10 N4 1.372(9) . ? C10 H10 0.9500 . ? C11 N3 1.488(9) . ? C11 C12 1.503(10) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.368(10) . ? C12 C14 1.395(11) . ? C13 C14 1.385(10) 2_655 ? C13 H13 0.9500 . ? C14 C13 1.385(10) 2_655 ? C14 H14 0.9500 . ? C15 O1 1.240(6) . ? C15 O2 1.282(6) . ? C15 C16 1.494(7) . ? C16 C17 1.383(7) . ? C16 C21 1.389(7) . ? C17 C18 1.409(7) . ? C17 H17 0.9500 . ? C18 C19 1.370(7) . ? C18 C22 1.504(7) . ? C19 C20 1.394(7) . ? C19 H19 0.9500 . ? C20 C21 1.379(8) . ? C20 N5 1.461(6) . ? C21 H21 0.9500 . ? C22 O3 1.262(6) . ? C22 O4 1.272(6) . ? Co1 O4 1.993(4) 1_655 ? Co1 O2 2.006(4) . ? Co1 N1 2.011(5) . ? Co1 N4 2.044(5) . ? Co1 O1 2.390(4) . ? N5 H5C 0.8800 . ? N5 H5D 0.8800 . ? O4 Co1 1.993(4) 1_455 ? O5 H5A 0.8583 . ? O5 H5B 0.8539 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 N2 111.6(5) . . ? N1 C1 H1 124.2 . . ? N2 C1 H1 124.2 . . ? C3 C2 N2 106.8(5) . . ? C3 C2 H2 126.6 . . ? N2 C2 H2 126.6 . . ? N1 C3 C2 110.3(6) . . ? N1 C3 H3 124.8 . . ? C2 C3 H3 124.8 . . ? N2 C4 C5 111.6(5) . . ? N2 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N2 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C7 C5 C6 118.3(6) . . ? C7 C5 C4 120.5(7) . . ? C6 C5 C4 121.1(6) . . ? C5 C6 C7 121.0(7) . 2_777 ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 2_777 . ? C5 C7 C6 120.6(7) . 2_777 ? C5 C7 H7 119.7 . . ? C6 C7 H7 119.7 2_777 . ? N4 C8 N3 111.2(7) . . ? N4 C8 H8 124.4 . . ? N3 C8 H8 124.4 . . ? N3 C9 C10 107.3(8) . . ? N3 C9 H9 126.4 . . ? C10 C9 H9 126.4 . . ? C9 C10 N4 109.3(8) . . ? C9 C10 H10 125.3 . . ? N4 C10 H10 125.3 . . ? N3 C11 C12 109.3(6) . . ? N3 C11 H11A 109.8 . . ? C12 C11 H11A 109.8 . . ? N3 C11 H11B 109.8 . . ? C12 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? C13 C12 C14 118.4(7) . . ? C13 C12 C11 119.2(8) . . ? C14 C12 C11 122.4(8) . . ? C12 C13 C14 120.6(7) . 2_655 ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 2_655 . ? C13 C14 C12 121.0(7) 2_655 . ? C13 C14 H14 119.5 2_655 . ? C12 C14 H14 119.5 . . ? O1 C15 O2 120.7(5) . . ? O1 C15 C16 121.4(5) . . ? O2 C15 C16 117.9(5) . . ? C17 C16 C21 119.7(5) . . ? C17 C16 C15 120.1(5) . . ? C21 C16 C15 120.2(5) . . ? C16 C17 C18 119.6(5) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C19 C18 C17 119.8(5) . . ? C19 C18 C22 120.9(5) . . ? C17 C18 C22 119.3(5) . . ? C18 C19 C20 120.7(5) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C21 C20 C19 119.3(5) . . ? C21 C20 N5 120.7(5) . . ? C19 C20 N5 120.0(5) . . ? C20 C21 C16 120.8(5) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? O3 C22 O4 123.6(5) . . ? O3 C22 C18 119.0(5) . . ? O4 C22 C18 117.3(5) . . ? O4 Co1 O2 99.91(14) 1_655 . ? O4 Co1 N1 100.87(18) 1_655 . ? O2 Co1 N1 111.05(18) . . ? O4 Co1 N4 99.86(19) 1_655 . ? O2 Co1 N4 109.5(2) . . ? N1 Co1 N4 129.93(19) . . ? O4 Co1 O1 158.79(14) 1_655 . ? O2 Co1 O1 59.06(14) . . ? N1 Co1 O1 90.45(17) . . ? N4 Co1 O1 86.03(19) . . ? C1 N1 C3 105.3(5) . . ? C1 N1 Co1 120.8(4) . . ? C3 N1 Co1 133.9(4) . . ? C1 N2 C2 106.0(5) . . ? C1 N2 C4 125.5(5) . . ? C2 N2 C4 128.4(6) . . ? C9 N3 C8 107.1(7) . . ? C9 N3 C11 126.9(8) . . ? C8 N3 C11 125.6(7) . . ? C8 N4 C10 105.0(6) . . ? C8 N4 Co1 129.4(5) . . ? C10 N4 Co1 124.9(5) . . ? C20 N5 H5C 120.0 . . ? C20 N5 H5D 120.0 . . ? H5C N5 H5D 120.0 . . ? C15 O1 Co1 81.8(3) . . ? C15 O2 Co1 98.3(3) . . ? C22 O4 Co1 117.0(3) . 1_455 ? H5A O5 H5B 113.8 . . ? 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 N2 C2 C3 N1 1.5(7) . . . . ? N2 C4 C5 C7 121.5(7) . . . . ? N2 C4 C5 C6 -61.0(9) . . . . ? C7 C5 C6 C7 -1.5(13) . . . 2_777 ? C4 C5 C6 C7 -179.0(7) . . . 2_777 ? C6 C5 C7 C6 1.5(13) . . . 2_777 ? C4 C5 C7 C6 179.0(7) . . . 2_777 ? N3 C9 C10 N4 -3.3(12) . . . . ? N3 C11 C12 C13 99.3(9) . . . . ? N3 C11 C12 C14 -79.1(9) . . . . ? C14 C12 C13 C14 0.0(12) . . . 2_655 ? C11 C12 C13 C14 -178.5(7) . . . 2_655 ? C13 C12 C14 C13 0.0(12) . . . 2_655 ? C11 C12 C14 C13 178.4(7) . . . 2_655 ? O1 C15 C16 C17 -3.2(9) . . . . ? O2 C15 C16 C17 176.8(5) . . . . ? O1 C15 C16 C21 176.4(6) . . . . ? O2 C15 C16 C21 -3.6(9) . . . . ? C21 C16 C17 C18 1.6(9) . . . . ? C15 C16 C17 C18 -178.8(5) . . . . ? C16 C17 C18 C19 -0.1(9) . . . . ? C16 C17 C18 C22 -178.0(5) . . . . ? C17 C18 C19 C20 -0.3(9) . . . . ? C22 C18 C19 C20 177.6(6) . . . . ? C18 C19 C20 C21 -0.9(9) . . . . ? C18 C19 C20 N5 -179.9(5) . . . . ? C19 C20 C21 C16 2.5(9) . . . . ? N5 C20 C21 C16 -178.6(5) . . . . ? C17 C16 C21 C20 -2.8(9) . . . . ? C15 C16 C21 C20 177.6(6) . . . . ? C19 C18 C22 O3 -171.3(6) . . . . ? C17 C18 C22 O3 6.5(9) . . . . ? C19 C18 C22 O4 7.5(9) . . . . ? C17 C18 C22 O4 -174.6(5) . . . . ? N2 C1 N1 C3 1.6(6) . . . . ? N2 C1 N1 Co1 -178.9(3) . . . . ? C2 C3 N1 C1 -1.9(7) . . . . ? C2 C3 N1 Co1 178.7(4) . . . . ? O4 Co1 N1 C1 18.8(4) 1_655 . . . ? O2 Co1 N1 C1 -86.4(4) . . . . ? N4 Co1 N1 C1 131.6(4) . . . . ? O1 Co1 N1 C1 -143.2(4) . . . . ? O4 Co1 N1 C3 -161.9(5) 1_655 . . . ? O2 Co1 N1 C3 93.0(5) . . . . ? N4 Co1 N1 C3 -49.0(6) . . . . ? O1 Co1 N1 C3 36.2(5) . . . . ? N1 C1 N2 C2 -0.7(6) . . . . ? N1 C1 N2 C4 176.8(5) . . . . ? C3 C2 N2 C1 -0.5(7) . . . . ? C3 C2 N2 C4 -177.9(6) . . . . ? C5 C4 N2 C1 116.6(7) . . . . ? C5 C4 N2 C2 -66.5(9) . . . . ? C10 C9 N3 C8 2.9(11) . . . . ? C10 C9 N3 C11 -170.5(8) . . . . ? N4 C8 N3 C9 -1.6(9) . . . . ? N4 C8 N3 C11 171.9(6) . . . . ? C12 C11 N3 C9 76.9(11) . . . . ? C12 C11 N3 C8 -95.3(10) . . . . ? N3 C8 N4 C10 -0.4(8) . . . . ? N3 C8 N4 Co1 170.4(4) . . . . ? C9 C10 N4 C8 2.3(11) . . . . ? C9 C10 N4 Co1 -169.1(7) . . . . ? O4 Co1 N4 C8 -177.7(6) 1_655 . . . ? O2 Co1 N4 C8 -73.4(6) . . . . ? N1 Co1 N4 C8 69.0(6) . . . . ? O1 Co1 N4 C8 -18.2(6) . . . . ? O4 Co1 N4 C10 -8.5(7) 1_655 . . . ? O2 Co1 N4 C10 95.8(7) . . . . ? N1 Co1 N4 C10 -121.7(7) . . . . ? O1 Co1 N4 C10 151.0(7) . . . . ? O2 C15 O1 Co1 3.7(5) . . . . ? C16 C15 O1 Co1 -176.3(5) . . . . ? O4 Co1 O1 C15 -10.7(7) 1_655 . . . ? O2 Co1 O1 C15 -2.3(3) . . . . ? N1 Co1 O1 C15 112.1(4) . . . . ? N4 Co1 O1 C15 -117.9(4) . . . . ? O1 C15 O2 Co1 -4.4(6) . . . . ? C16 C15 O2 Co1 175.6(4) . . . . ? O4 Co1 O2 C15 179.2(4) 1_655 . . . ? N1 Co1 O2 C15 -75.0(4) . . . . ? N4 Co1 O2 C15 75.0(4) . . . . ? O1 Co1 O2 C15 2.3(3) . . . . ? O3 C22 O4 Co1 0.6(8) . . . 1_455 ? C18 C22 O4 Co1 -178.2(4) . . . 1_455 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5B O3 0.85 2.20 2.969(7) 149.9 2_666 O5 H5A O3 0.86 2.03 2.842(6) 157.6 1_655 N5 H5C O5 0.88 1.83 2.661(6) 157.3 1_565 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.94 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.264 _refine_diff_density_min -0.799 _refine_diff_density_rms 0.142 data_4# _database_code_depnum_ccdc_archive 'CCDC 821496' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H31 Co2 N8 O8' _chemical_formula_weight 833.56 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 10.7631(4) _cell_length_b 11.1927(4) _cell_length_c 15.5583(6) _cell_angle_alpha 107.1090(10) _cell_angle_beta 95.3050(9) _cell_angle_gamma 99.1550(10) _cell_volume 1749.15(11) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7990 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 27.85 _exptl_crystal_description Block _exptl_crystal_colour Purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 854 _exptl_absorpt_coefficient_mu 1.016 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8227 _exptl_absorpt_correction_T_max 0.8227 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8952 _diffrn_reflns_av_R_equivalents 0.0095 _diffrn_reflns_av_sigmaI/netI 0.0164 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6118 _reflns_number_gt 5603 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0543P)^2^+1.4690P] 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 6118 _refine_ls_number_parameters 514 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0957 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3374(2) 0.2327(2) -0.07770(14) 0.0260(4) Uani 1 1 d . . . C2 C 0.3091(2) 0.3188(2) -0.00088(14) 0.0274(4) Uani 1 1 d . . . H2 H 0.3498 0.4039 0.0177 0.033 Uiso 1 1 calc R . . C3 C 0.2191(2) 0.2763(2) 0.04796(14) 0.0273(4) Uani 1 1 d . . . C4 C 0.1571(2) 0.1501(2) 0.01913(14) 0.0282(5) Uani 1 1 d . . . H4 H 0.0988 0.1216 0.0528 0.034 Uiso 1 1 calc R . . C5 C 0.1816(2) 0.0658(2) -0.05984(15) 0.0273(4) Uani 1 1 d U . . C6 C 0.2726(2) 0.1071(2) -0.10783(14) 0.0278(5) Uani 1 1 d . . . H6 H 0.2901 0.0505 -0.1603 0.033 Uiso 1 1 calc R . . C7 C 0.4401(2) 0.2757(2) -0.12710(14) 0.0275(5) Uani 1 1 d . . . C8 C 0.1880(2) 0.3664(2) 0.13180(15) 0.0298(5) Uani 1 1 d . A . C9 C -0.1864(2) 0.2209(2) 0.39449(15) 0.0296(5) Uani 1 1 d . . . C10 C 0.1989(2) 0.6957(2) 0.52259(15) 0.0299(5) Uani 1 1 d . . . H10 H 0.1432 0.6175 0.4983 0.036 Uiso 1 1 calc R . . C11 C 0.2958(2) 0.7301(2) 0.47578(14) 0.0290(5) Uani 1 1 d . . . C12 C 0.3791(2) 0.8460(2) 0.51185(15) 0.0339(5) Uani 1 1 d . . . H12 H 0.4432 0.8686 0.4802 0.041 Uiso 1 1 calc R . . C13 C 0.3667(2) 0.9283(2) 0.59547(16) 0.0351(5) Uani 1 1 d U . . C14 C -0.2699(2) 0.1046(2) 0.35839(15) 0.0350(5) Uani 1 1 d . . . H14 H -0.2607 0.0486 0.3029 0.042 Uiso 1 1 calc R . . C15 C -0.0883(2) 0.2582(2) 0.33990(16) 0.0349(5) Uani 1 1 d . A . C16 C 0.3086(2) 0.6413(2) 0.38507(15) 0.0297(5) Uani 1 1 d . A . C17 C 0.2653(3) 0.8628(3) 0.23444(18) 0.0453(6) Uani 1 1 d . . . H17 H 0.3174 0.9036 0.2899 0.054 Uiso 1 1 calc R . . C18 C 0.1787(3) 0.7251(3) 0.10767(19) 0.0477(6) Uani 1 1 d . . . H18 H 0.1598 0.6508 0.0582 0.057 Uiso 1 1 calc R . . C19 C 0.1211(3) 0.8251(3) 0.1173(2) 0.0573(8) Uani 1 1 d . . . H19 H 0.0562 0.8328 0.0766 0.069 Uiso 1 1 calc R . . C20 C 0.1774(8) 1.0605(8) 0.2368(6) 0.054(2) Uani 0.50 1 d PU . 1 H20A H 0.2514 1.1080 0.2220 0.065 Uiso 0.50 1 calc PR . 1 H20B H 0.1020 1.0797 0.2087 0.065 Uiso 0.50 1 calc PR . 1 C21 C -0.1806(4) 0.9013(3) 0.6650(2) 0.0645(10) Uani 1 1 d . . . C22 C -0.2616(5) 0.7893(5) 0.6292(4) 0.0978(15) Uani 1 1 d . . . H22 H -0.2994 0.7497 0.6677 0.117 Uiso 1 1 calc R . . C23 C -0.2896(4) 0.7326(4) 0.5379(4) 0.0938(14) Uani 1 1 d . A . H23 H -0.3472 0.6554 0.5153 0.113 Uiso 1 1 calc R . . C24 C -0.2357(3) 0.7856(3) 0.4781(2) 0.0576(8) Uani 1 1 d . . . C25 C -0.1535(4) 0.8995(4) 0.5141(2) 0.0758(11) Uani 1 1 d . A . H25 H -0.1161 0.9395 0.4757 0.091 Uiso 1 1 calc R . . C26 C -0.1252(4) 0.9564(4) 0.6073(2) 0.0793(11) Uani 1 1 d . . . H26 H -0.0675 1.0334 0.6308 0.095 Uiso 1 1 calc R A . C27 C -0.2849(10) 0.7085(11) 0.3857(7) 0.056(3) Uani 0.50 1 d PU A 1 H27A H -0.3330 0.7555 0.3562 0.067 Uiso 0.50 1 calc PR A 1 H27B H -0.3419 0.6320 0.3855 0.067 Uiso 0.50 1 calc PR A 1 C28 C -0.1075(3) 0.5870(3) 0.3506(2) 0.0571(8) Uani 1 1 d . A . H28 H -0.1160 0.5589 0.4008 0.069 Uiso 1 1 calc R . . C29 C -0.0482(4) 0.6135(5) 0.2304(3) 0.0826(12) Uani 1 1 d . A . H29 H -0.0063 0.6076 0.1801 0.099 Uiso 1 1 calc R . . C30 C -0.1332(4) 0.6855(5) 0.2534(3) 0.0909(13) Uani 1 1 d . A . H30 H -0.1619 0.7376 0.2223 0.109 Uiso 1 1 calc R . . C31 C 0.5553(2) 0.4231(2) 0.14890(17) 0.0357(5) Uani 1 1 d . . . H31 H 0.5652 0.4417 0.0952 0.043 Uiso 1 1 calc R . . C32 C 0.5027(3) 0.4278(3) 0.27908(18) 0.0465(6) Uani 1 1 d . . . H32 H 0.4682 0.4510 0.3328 0.056 Uiso 1 1 calc R . . C33 C 0.5678(3) 0.3331(3) 0.2549(2) 0.0552(8) Uani 1 1 d . . . H33 H 0.5869 0.2800 0.2883 0.066 Uiso 1 1 calc R . . C34 C 0.6639(3) 0.2377(3) 0.1128(2) 0.0560(8) Uani 1 1 d . . . H34A H 0.7277 0.2160 0.1507 0.067 Uiso 1 1 calc R . . H34B H 0.7076 0.2776 0.0735 0.067 Uiso 1 1 calc R . . C35 C 0.5753(3) 0.1167(2) 0.05462(19) 0.0430(6) Uani 1 1 d . . . C36 C 0.4796(3) 0.0531(3) 0.0872(2) 0.0563(8) Uani 1 1 d . . . H36 H 0.4645 0.0881 0.1464 0.068 Uiso 1 1 calc R . . C37 C 0.4056(3) -0.0619(3) 0.0330(2) 0.0535(7) Uani 1 1 d . . . H37 H 0.3415 -0.1029 0.0565 0.064 Uiso 1 1 calc R . . C20' C 0.1176(9) 1.0202(9) 0.2315(6) 0.061(2) Uani 0.50 1 d PU . 2 H20C H 0.0270 0.9913 0.2290 0.073 Uiso 0.50 1 calc PR . 2 H20D H 0.1289 1.0751 0.1937 0.073 Uiso 0.50 1 calc PR . 2 C27' C -0.2564(11) 0.7448(11) 0.3683(7) 0.057(3) Uani 0.50 1 d PU A 2 H27C H -0.3427 0.6978 0.3449 0.068 Uiso 0.50 1 calc PR A 2 H27D H -0.2458 0.8210 0.3499 0.068 Uiso 0.50 1 calc PR A 2 Co1 Co 0.38613(3) 0.62323(3) 0.201238(18) 0.02610(10) Uani 1 1 d . . . Co2 Co 0.08704(3) 0.42630(3) 0.29489(2) 0.03552(11) Uani 1 1 d . A . N1 N 0.49466(19) 0.48523(18) 0.21234(13) 0.0343(4) Uani 1 1 d . . . N2 N 0.6006(2) 0.3302(2) 0.17132(15) 0.0435(5) Uani 1 1 d . . . N3 N 0.26897(19) 0.74841(19) 0.18106(13) 0.0344(4) Uani 1 1 d . . . N4 N 0.1762(3) 0.9131(3) 0.19826(16) 0.0568(7) Uani 1 1 d . . . N5 N -0.1711(3) 0.6698(3) 0.33030(18) 0.0612(7) Uani 1 1 d . . . N6 N -0.0307(2) 0.5492(2) 0.29101(16) 0.0473(5) Uani 1 1 d . . . N7 N 0.11410(15) -0.05813(16) -0.08576(11) 0.0227(4) Uani 1 1 d U . . H7A H 0.1272 -0.0983 -0.0477 0.027 Uiso 1 1 d R . . H7B H 0.1133 -0.0888 -0.1402 0.027 Uiso 1 1 d R . . N8 N 0.4531(2) 1.04127(18) 0.62913(13) 0.0388(5) Uani 1 1 d U . . H8A H 0.4376 1.0804 0.6795 0.047 Uiso 1 1 d R . . H8B H 0.5097 1.0041 0.6452 0.047 Uiso 1 1 d R . . O1 O 0.52687(15) 0.36950(15) -0.08431(10) 0.0333(4) Uani 1 1 d . . . O2 O 0.43729(16) 0.21997(16) -0.21066(10) 0.0362(4) Uani 1 1 d . . . O3 O 0.12155(18) 0.31653(16) 0.18004(11) 0.0439(5) Uani 1 1 d . . . O4 O 0.22402(16) 0.48317(15) 0.14997(11) 0.0358(4) Uani 1 1 d . . . O5 O -0.00082(18) 0.35335(17) 0.37939(13) 0.0460(5) Uani 1 1 d . . . O6 O -0.0987(2) 0.1975(2) 0.25811(12) 0.0614(6) Uani 1 1 d . . . O7 O 0.38038(16) 0.68420(15) 0.33802(10) 0.0362(4) Uani 1 1 d . . . O8 O 0.24918(17) 0.52803(16) 0.36345(11) 0.0409(4) 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 C1 0.0265(10) 0.0315(11) 0.0213(10) 0.0085(9) 0.0098(8) 0.0050(9) C2 0.0297(11) 0.0271(11) 0.0236(10) 0.0051(9) 0.0107(8) 0.0020(9) C3 0.0285(11) 0.0303(11) 0.0208(10) 0.0041(9) 0.0087(8) 0.0035(9) C4 0.0282(11) 0.0314(12) 0.0233(10) 0.0063(9) 0.0116(8) 0.0011(9) C5 0.0266(10) 0.0240(9) 0.0268(11) 0.0032(8) 0.0070(8) -0.0006(8) C6 0.0308(11) 0.0302(11) 0.0197(10) 0.0019(8) 0.0086(8) 0.0066(9) C7 0.0317(11) 0.0283(11) 0.0253(11) 0.0085(9) 0.0137(9) 0.0080(9) C8 0.0291(11) 0.0298(12) 0.0263(11) 0.0030(9) 0.0123(9) 0.0004(9) C9 0.0319(11) 0.0336(12) 0.0241(11) 0.0087(9) 0.0124(9) 0.0043(9) C10 0.0326(11) 0.0286(11) 0.0256(11) 0.0054(9) 0.0107(9) -0.0004(9) C11 0.0354(12) 0.0276(11) 0.0223(10) 0.0043(9) 0.0119(9) 0.0035(9) C12 0.0373(12) 0.0321(12) 0.0283(11) 0.0045(9) 0.0180(10) -0.0023(10) C13 0.0401(13) 0.0260(11) 0.0299(12) 0.0004(9) 0.0122(10) -0.0083(9) C14 0.0449(13) 0.0327(12) 0.0223(11) 0.0003(9) 0.0147(10) 0.0033(10) C15 0.0362(13) 0.0379(13) 0.0345(13) 0.0130(11) 0.0170(10) 0.0080(11) C16 0.0331(11) 0.0280(11) 0.0251(11) 0.0042(9) 0.0100(9) 0.0017(9) C17 0.0585(17) 0.0466(15) 0.0351(13) 0.0099(12) 0.0088(12) 0.0274(13) C18 0.0478(15) 0.0518(16) 0.0392(14) 0.0125(12) 0.0040(12) 0.0027(13) C19 0.0514(17) 0.085(2) 0.0436(16) 0.0264(16) 0.0069(13) 0.0257(16) C20 0.066(5) 0.052(5) 0.057(4) 0.020(4) 0.017(4) 0.035(4) C21 0.095(3) 0.067(2) 0.0530(18) 0.0233(16) 0.0265(17) 0.059(2) C22 0.127(4) 0.079(3) 0.109(4) 0.047(3) 0.059(3) 0.027(3) C23 0.090(3) 0.057(2) 0.120(4) 0.014(2) 0.025(3) -0.005(2) C24 0.0469(16) 0.0523(18) 0.0621(19) -0.0047(15) -0.0003(14) 0.0249(14) C25 0.088(3) 0.078(3) 0.0476(18) 0.0075(17) 0.0191(17) -0.007(2) C26 0.088(3) 0.069(2) 0.056(2) -0.0045(17) 0.0093(19) -0.010(2) C27 0.048(5) 0.061(6) 0.053(5) 0.001(4) 0.007(3) 0.026(4) C28 0.072(2) 0.0625(19) 0.0444(16) 0.0141(14) 0.0215(15) 0.0333(17) C29 0.077(3) 0.121(4) 0.077(3) 0.061(3) 0.029(2) 0.030(2) C30 0.089(3) 0.108(3) 0.102(3) 0.066(3) 0.011(3) 0.032(3) C31 0.0392(13) 0.0318(12) 0.0340(12) 0.0052(10) 0.0087(10) 0.0091(10) C32 0.0652(18) 0.0437(15) 0.0346(13) 0.0129(12) 0.0144(12) 0.0171(13) C33 0.078(2) 0.0487(17) 0.0469(16) 0.0193(14) 0.0084(15) 0.0263(15) C34 0.0472(16) 0.0438(16) 0.071(2) 0.0007(14) 0.0127(14) 0.0217(13) C35 0.0441(14) 0.0351(13) 0.0531(16) 0.0108(12) 0.0118(12) 0.0205(11) C36 0.0645(19) 0.0534(18) 0.0471(16) 0.0050(14) 0.0223(14) 0.0127(15) C37 0.0597(18) 0.0478(17) 0.0542(17) 0.0129(14) 0.0258(14) 0.0093(14) C20' 0.079(5) 0.061(5) 0.047(4) 0.008(4) 0.002(4) 0.044(4) C27' 0.054(5) 0.058(5) 0.050(5) 0.002(4) 0.003(4) 0.019(4) Co1 0.03269(17) 0.02326(16) 0.02224(16) 0.00439(12) 0.01486(12) 0.00420(12) Co2 0.03886(19) 0.03102(19) 0.02906(18) -0.00191(13) 0.02104(14) -0.00263(14) N1 0.0429(11) 0.0295(10) 0.0303(10) 0.0059(8) 0.0107(8) 0.0095(9) N2 0.0458(12) 0.0378(12) 0.0451(12) 0.0050(10) 0.0086(10) 0.0171(10) N3 0.0371(11) 0.0344(11) 0.0335(10) 0.0100(9) 0.0127(8) 0.0091(9) N4 0.0754(17) 0.0707(17) 0.0415(13) 0.0217(12) 0.0196(12) 0.0500(15) N5 0.0633(16) 0.0557(16) 0.0528(15) -0.0035(12) -0.0065(13) 0.0260(13) N6 0.0533(14) 0.0492(13) 0.0410(12) 0.0123(10) 0.0186(10) 0.0111(11) N7 0.0249(9) 0.0204(8) 0.0182(8) 0.0004(6) 0.0130(7) -0.0034(6) N8 0.0462(12) 0.0223(9) 0.0310(10) -0.0118(8) 0.0241(9) -0.0134(8) O1 0.0353(9) 0.0318(9) 0.0308(8) 0.0059(7) 0.0171(7) 0.0012(7) O2 0.0432(9) 0.0401(9) 0.0240(8) 0.0060(7) 0.0178(7) 0.0045(7) O3 0.0580(11) 0.0341(9) 0.0321(9) -0.0008(7) 0.0303(8) -0.0052(8) O4 0.0397(9) 0.0271(8) 0.0354(9) 0.0018(7) 0.0152(7) 0.0015(7) O5 0.0485(10) 0.0383(10) 0.0491(11) 0.0090(8) 0.0297(9) -0.0016(8) O6 0.0619(13) 0.0838(16) 0.0286(10) 0.0055(10) 0.0265(9) -0.0029(11) O7 0.0466(10) 0.0327(9) 0.0247(8) 0.0021(7) 0.0198(7) -0.0006(7) O8 0.0475(10) 0.0293(9) 0.0355(9) -0.0010(7) 0.0139(8) -0.0053(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.387(3) . ? C1 C2 1.390(3) . ? C1 C7 1.500(3) . ? C2 C3 1.394(3) . ? C2 H2 0.9300 . ? C3 C4 1.383(3) . ? C3 C8 1.498(3) . ? C4 C5 1.388(3) . ? C4 H4 0.9300 . ? C5 N7 1.382(3) . ? C5 C6 1.387(3) . ? C6 H6 0.9300 . ? C7 O1 1.257(3) . ? C7 O2 1.261(3) . ? C8 O4 1.241(3) . ? C8 O3 1.267(3) . ? C9 C10 1.384(3) 2_566 ? C9 C14 1.386(3) . ? C9 C15 1.499(3) . ? C10 C9 1.384(3) 2_566 ? C10 C11 1.394(3) . ? C10 H10 0.9300 . ? C11 C12 1.382(3) . ? C11 C16 1.501(3) . ? C12 C13 1.388(3) . ? C12 H12 0.9300 . ? C13 N8 1.372(3) . ? C13 C14 1.382(3) 2_566 ? C14 C13 1.382(3) 2_566 ? C14 H14 0.9300 . ? C15 O6 1.239(3) . ? C15 O5 1.260(3) . ? C16 O7 1.248(3) . ? C16 O8 1.257(3) . ? C17 N3 1.314(3) . ? C17 N4 1.346(3) . ? C17 H17 0.9300 . ? C18 C19 1.342(4) . ? C18 N3 1.362(3) . ? C18 H18 0.9300 . ? C19 N4 1.362(4) . ? C19 H19 0.9300 . ? C20 C21 1.457(10) 2_576 ? C20 N4 1.579(9) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.339(6) . ? C21 C26 1.360(5) . ? C21 C20 1.457(10) 2_576 ? C21 C20' 1.613(9) 2_576 ? C22 C23 1.357(7) . ? C22 H22 0.9300 . ? C23 C24 1.367(6) . ? C23 H23 0.9300 . ? C24 C25 1.360(5) . ? C24 C27 1.441(11) . ? C24 C27' 1.618(11) . ? C25 C26 1.384(5) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 N5 1.605(11) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 N6 1.320(4) . ? C28 N5 1.327(4) . ? C28 H28 0.9300 . ? C29 C30 1.319(6) . ? C29 N6 1.361(4) . ? C29 H29 0.9300 . ? C30 N5 1.349(5) . ? C30 H30 0.9300 . ? C31 N1 1.320(3) . ? C31 N2 1.336(3) . ? C31 H31 0.9300 . ? C32 C33 1.345(4) . ? C32 N1 1.376(3) . ? C32 H32 0.9300 . ? C33 N2 1.371(4) . ? C33 H33 0.9300 . ? C34 N2 1.466(3) . ? C34 C35 1.507(4) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C37 1.370(4) 2_655 ? C35 C36 1.378(4) . ? C36 C37 1.383(4) . ? C36 H36 0.9300 . ? C37 C35 1.370(4) 2_655 ? C37 H37 0.9300 . ? C20' N4 1.428(9) . ? C20' C21 1.613(9) 2_576 ? C20' H20C 0.9700 . ? C20' H20D 0.9700 . ? C27' N5 1.397(12) . ? C27' H27C 0.9700 . ? C27' H27D 0.9700 . ? Co1 O7 2.0448(15) . ? Co1 O4 2.0675(16) . ? Co1 N3 2.097(2) . ? Co1 N1 2.115(2) . ? Co1 O1 2.1380(15) 2_665 ? Co1 O2 2.3345(17) 2_665 ? Co2 O8 1.9464(17) . ? Co2 O3 1.9537(16) . ? Co2 O5 1.9761(17) . ? Co2 N6 2.023(2) . ? N7 H7A 0.8569 . ? N7 H7B 0.8140 . ? N8 H8A 0.8243 . ? N8 H8B 0.8491 . ? O1 Co1 2.1380(15) 2_665 ? O2 Co1 2.3345(16) 2_665 ? 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 C6 C1 C2 120.32(19) . . ? C6 C1 C7 120.01(19) . . ? C2 C1 C7 119.67(19) . . ? C1 C2 C3 119.3(2) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 120.18(19) . . ? C4 C3 C8 119.23(19) . . ? C2 C3 C8 120.59(19) . . ? C3 C4 C5 120.22(19) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N7 C5 C6 123.05(19) . . ? N7 C5 C4 117.13(19) . . ? C6 C5 C4 119.8(2) . . ? C1 C6 C5 120.05(19) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? O1 C7 O2 120.85(19) . . ? O1 C7 C1 118.92(18) . . ? O2 C7 C1 120.2(2) . . ? O4 C8 O3 123.2(2) . . ? O4 C8 C3 120.40(19) . . ? O3 C8 C3 116.35(19) . . ? C10 C9 C14 120.2(2) 2_566 . ? C10 C9 C15 120.7(2) 2_566 . ? C14 C9 C15 119.1(2) . . ? C9 C10 C11 119.4(2) 2_566 . ? C9 C10 H10 120.3 2_566 . ? C11 C10 H10 120.3 . . ? C12 C11 C10 120.5(2) . . ? C12 C11 C16 119.81(19) . . ? C10 C11 C16 119.7(2) . . ? C11 C12 C13 119.8(2) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? N8 C13 C14 122.4(2) . 2_566 ? N8 C13 C12 117.6(2) . . ? C14 C13 C12 120.0(2) 2_566 . ? C13 C14 C9 120.2(2) 2_566 . ? C13 C14 H14 119.9 2_566 . ? C9 C14 H14 119.9 . . ? O6 C15 O5 123.1(2) . . ? O6 C15 C9 119.1(2) . . ? O5 C15 C9 117.8(2) . . ? O7 C16 O8 124.9(2) . . ? O7 C16 C11 117.65(19) . . ? O8 C16 C11 117.43(19) . . ? N3 C17 N4 111.1(2) . . ? N3 C17 H17 124.5 . . ? N4 C17 H17 124.5 . . ? C19 C18 N3 109.9(3) . . ? C19 C18 H18 125.0 . . ? N3 C18 H18 125.0 . . ? C18 C19 N4 106.5(3) . . ? C18 C19 H19 126.7 . . ? N4 C19 H19 126.7 . . ? C21 C20 N4 110.1(6) 2_576 . ? C21 C20 H20A 109.6 2_576 . ? N4 C20 H20A 109.6 . . ? C21 C20 H20B 109.6 2_576 . ? N4 C20 H20B 109.6 . . ? H20A C20 H20B 108.2 . . ? C22 C21 C26 118.2(4) . . ? C22 C21 C20 107.7(5) . 2_576 ? C26 C21 C20 134.0(5) . 2_576 ? C22 C21 C20' 131.5(5) . 2_576 ? C26 C21 C20' 109.7(5) . 2_576 ? C21 C22 C23 121.3(4) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C22 C23 C24 121.9(4) . . ? C22 C23 H23 119.0 . . ? C24 C23 H23 119.0 . . ? C25 C24 C23 117.0(3) . . ? C25 C24 C27 132.3(5) . . ? C23 C24 C27 110.6(5) . . ? C25 C24 C27' 110.2(5) . . ? C23 C24 C27' 132.6(5) . . ? C24 C25 C26 120.6(4) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C21 C26 C25 120.9(4) . . ? C21 C26 H26 119.5 . . ? C25 C26 H26 119.6 . . ? C24 C27 N5 110.6(7) . . ? C24 C27 H27A 109.5 . . ? N5 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? N5 C27 H27B 109.5 . . ? H27A C27 H27B 108.1 . . ? N6 C28 N5 111.9(3) . . ? N6 C28 H28 124.1 . . ? N5 C28 H28 124.1 . . ? C30 C29 N6 110.1(3) . . ? C30 C29 H29 125.0 . . ? N6 C29 H29 125.0 . . ? C29 C30 N5 107.5(3) . . ? C29 C30 H30 126.2 . . ? N5 C30 H30 126.2 . . ? N1 C31 N2 111.7(2) . . ? N1 C31 H31 124.2 . . ? N2 C31 H31 124.2 . . ? C33 C32 N1 109.8(2) . . ? C33 C32 H32 125.1 . . ? N1 C32 H32 125.1 . . ? C32 C33 N2 106.4(2) . . ? C32 C33 H33 126.8 . . ? N2 C33 H33 126.8 . . ? N2 C34 C35 114.1(2) . . ? N2 C34 H34A 108.7 . . ? C35 C34 H34A 108.7 . . ? N2 C34 H34B 108.7 . . ? C35 C34 H34B 108.7 . . ? H34A C34 H34B 107.6 . . ? C37 C35 C36 117.7(3) 2_655 . ? C37 C35 C34 119.3(3) 2_655 . ? C36 C35 C34 122.9(3) . . ? C35 C36 C37 121.0(3) . . ? C35 C36 H36 119.5 . . ? C37 C36 H36 119.5 . . ? C35 C37 C36 121.4(3) 2_655 . ? C35 C37 H37 119.3 2_655 . ? C36 C37 H37 119.3 . . ? N4 C20' C21 109.7(6) . 2_576 ? N4 C20' H20C 109.7 . . ? C21 C20' H20C 109.7 2_576 . ? N4 C20' H20D 109.7 . . ? C21 C20' H20D 109.7 2_576 . ? H20C C20' H20D 108.2 . . ? N5 C27' C24 112.3(8) . . ? N5 C27' H27C 109.2 . . ? C24 C27' H27C 109.2 . . ? N5 C27' H27D 109.2 . . ? C24 C27' H27D 109.2 . . ? H27C C27' H27D 107.9 . . ? O7 Co1 O4 103.75(6) . . ? O7 Co1 N3 90.68(7) . . ? O4 Co1 N3 85.12(7) . . ? O7 Co1 N1 92.61(7) . . ? O4 Co1 N1 90.80(7) . . ? N3 Co1 N1 175.27(8) . . ? O7 Co1 O1 151.86(6) . 2_665 ? O4 Co1 O1 104.39(6) . 2_665 ? N3 Co1 O1 91.48(7) . 2_665 ? N1 Co1 O1 87.22(7) . 2_665 ? O7 Co1 O2 93.58(6) . 2_665 ? O4 Co1 O2 161.60(6) . 2_665 ? N3 Co1 O2 88.61(7) . 2_665 ? N1 Co1 O2 94.57(7) . 2_665 ? O1 Co1 O2 58.43(6) 2_665 2_665 ? O8 Co2 O3 107.56(8) . . ? O8 Co2 O5 106.35(8) . . ? O3 Co2 O5 121.02(7) . . ? O8 Co2 N6 106.81(9) . . ? O3 Co2 N6 118.54(9) . . ? O5 Co2 N6 95.16(9) . . ? C31 N1 C32 105.1(2) . . ? C31 N1 Co1 125.92(17) . . ? C32 N1 Co1 128.33(17) . . ? C31 N2 C33 107.0(2) . . ? C31 N2 C34 125.3(2) . . ? C33 N2 C34 127.6(2) . . ? C17 N3 C18 105.7(2) . . ? C17 N3 Co1 128.60(18) . . ? C18 N3 Co1 125.70(18) . . ? C17 N4 C19 106.8(2) . . ? C17 N4 C20' 134.8(4) . . ? C19 N4 C20' 117.4(4) . . ? C17 N4 C20 119.8(4) . . ? C19 N4 C20 131.0(4) . . ? C28 N5 C30 106.2(3) . . ? C28 N5 C27' 137.9(5) . . ? C30 N5 C27' 115.8(5) . . ? C28 N5 C27 118.6(5) . . ? C30 N5 C27 134.2(5) . . ? C28 N6 C29 104.3(3) . . ? C28 N6 Co2 126.1(2) . . ? C29 N6 Co2 129.6(2) . . ? C5 N7 H7A 114.7 . . ? C5 N7 H7B 107.5 . . ? H7A N7 H7B 123.3 . . ? C13 N8 H8A 108.6 . . ? C13 N8 H8B 91.5 . . ? H8A N8 H8B 99.7 . . ? C7 O1 Co1 94.83(12) . 2_665 ? C7 O2 Co1 85.75(13) . 2_665 ? C8 O3 Co2 118.86(15) . . ? C8 O4 Co1 140.50(16) . . ? C15 O5 Co2 113.55(16) . . ? C16 O7 Co1 130.80(15) . . ? C16 O8 Co2 138.16(17) . . ? 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 C6 C1 C2 C3 3.0(3) . . . . ? C7 C1 C2 C3 -176.0(2) . . . . ? C1 C2 C3 C4 -1.2(3) . . . . ? C1 C2 C3 C8 179.1(2) . . . . ? C2 C3 C4 C5 -1.6(3) . . . . ? C8 C3 C4 C5 178.1(2) . . . . ? C3 C4 C5 N7 -178.5(2) . . . . ? C3 C4 C5 C6 2.7(3) . . . . ? C2 C1 C6 C5 -1.9(3) . . . . ? C7 C1 C6 C5 177.1(2) . . . . ? N7 C5 C6 C1 -179.6(2) . . . . ? C4 C5 C6 C1 -0.9(3) . . . . ? C6 C1 C7 O1 -154.2(2) . . . . ? C2 C1 C7 O1 24.8(3) . . . . ? C6 C1 C7 O2 27.3(3) . . . . ? C2 C1 C7 O2 -153.7(2) . . . . ? C4 C3 C8 O4 -166.8(2) . . . . ? C2 C3 C8 O4 12.9(3) . . . . ? C4 C3 C8 O3 11.4(3) . . . . ? C2 C3 C8 O3 -168.9(2) . . . . ? C9 C10 C11 C12 0.3(4) 2_566 . . . ? C9 C10 C11 C16 -179.0(2) 2_566 . . . ? C10 C11 C12 C13 0.4(4) . . . . ? C16 C11 C12 C13 179.7(2) . . . . ? C11 C12 C13 N8 178.9(2) . . . . ? C11 C12 C13 C14 -1.2(4) . . . 2_566 ? C10 C9 C14 C13 0.6(4) 2_566 . . 2_566 ? C15 C9 C14 C13 -175.6(2) . . . 2_566 ? C10 C9 C15 O6 -162.4(2) 2_566 . . . ? C14 C9 C15 O6 13.8(4) . . . . ? C10 C9 C15 O5 15.3(4) 2_566 . . . ? C14 C9 C15 O5 -168.5(2) . . . . ? C12 C11 C16 O7 -12.1(3) . . . . ? C10 C11 C16 O7 167.2(2) . . . . ? C12 C11 C16 O8 165.8(2) . . . . ? C10 C11 C16 O8 -14.9(3) . . . . ? N3 C18 C19 N4 0.0(3) . . . . ? C26 C21 C22 C23 -1.0(7) . . . . ? C20 C21 C22 C23 176.5(5) 2_576 . . . ? C20' C21 C22 C23 -171.1(6) 2_576 . . . ? C21 C22 C23 C24 0.9(8) . . . . ? C22 C23 C24 C25 -1.0(7) . . . . ? C22 C23 C24 C27 -178.0(6) . . . . ? C22 C23 C24 C27' -176.0(7) . . . . ? C23 C24 C25 C26 1.2(6) . . . . ? C27 C24 C25 C26 177.5(7) . . . . ? C27' C24 C25 C26 177.3(6) . . . . ? C22 C21 C26 C25 1.2(6) . . . . ? C20 C21 C26 C25 -175.5(6) 2_576 . . . ? C20' C21 C26 C25 173.4(5) 2_576 . . . ? C24 C25 C26 C21 -1.4(7) . . . . ? C25 C24 C27 N5 58.9(10) . . . . ? C23 C24 C27 N5 -124.6(6) . . . . ? C27' C24 C27 N5 59.4(19) . . . . ? N6 C29 C30 N5 0.7(6) . . . . ? N1 C32 C33 N2 -0.4(4) . . . . ? N2 C34 C35 C37 140.8(3) . . . 2_655 ? N2 C34 C35 C36 -43.4(4) . . . . ? C37 C35 C36 C37 0.0(5) 2_655 . . . ? C34 C35 C36 C37 -175.9(3) . . . . ? C35 C36 C37 C35 0.0(5) . . . 2_655 ? C25 C24 C27' N5 91.7(7) . . . . ? C23 C24 C27' N5 -93.0(8) . . . . ? C27 C24 C27' N5 -88(2) . . . . ? N2 C31 N1 C32 0.1(3) . . . . ? N2 C31 N1 Co1 -171.47(16) . . . . ? C33 C32 N1 C31 0.2(3) . . . . ? C33 C32 N1 Co1 171.5(2) . . . . ? O7 Co1 N1 C31 -166.2(2) . . . . ? O4 Co1 N1 C31 89.9(2) . . . . ? O1 Co1 N1 C31 -14.4(2) 2_665 . . . ? O2 Co1 N1 C31 -72.4(2) 2_665 . . . ? O7 Co1 N1 C32 24.1(2) . . . . ? O4 Co1 N1 C32 -79.7(2) . . . . ? O1 Co1 N1 C32 175.9(2) 2_665 . . . ? O2 Co1 N1 C32 117.9(2) 2_665 . . . ? N1 C31 N2 C33 -0.4(3) . . . . ? N1 C31 N2 C34 175.2(2) . . . . ? C32 C33 N2 C31 0.5(3) . . . . ? C32 C33 N2 C34 -174.9(3) . . . . ? C35 C34 N2 C31 -91.3(3) . . . . ? C35 C34 N2 C33 83.4(4) . . . . ? N4 C17 N3 C18 0.2(3) . . . . ? N4 C17 N3 Co1 -179.46(18) . . . . ? C19 C18 N3 C17 -0.1(3) . . . . ? C19 C18 N3 Co1 179.54(19) . . . . ? O7 Co1 N3 C17 34.8(2) . . . . ? O4 Co1 N3 C17 138.5(2) . . . . ? O1 Co1 N3 C17 -117.2(2) 2_665 . . . ? O2 Co1 N3 C17 -58.8(2) 2_665 . . . ? O7 Co1 N3 C18 -144.8(2) . . . . ? O4 Co1 N3 C18 -41.1(2) . . . . ? O1 Co1 N3 C18 63.2(2) 2_665 . . . ? O2 Co1 N3 C18 121.6(2) 2_665 . . . ? N3 C17 N4 C19 -0.2(4) . . . . ? N3 C17 N4 C20' 167.3(7) . . . . ? N3 C17 N4 C20 -164.6(4) . . . . ? C18 C19 N4 C17 0.1(4) . . . . ? C18 C19 N4 C20' -170.0(5) . . . . ? C18 C19 N4 C20 162.1(5) . . . . ? C21 C20' N4 C17 3.2(11) 2_576 . . . ? C21 C20' N4 C19 169.8(4) 2_576 . . . ? C21 C20' N4 C20 -62.3(12) 2_576 . . . ? C21 C20 N4 C17 -52.5(7) 2_576 . . . ? C21 C20 N4 C19 147.4(4) 2_576 . . . ? C21 C20 N4 C20' 79.3(14) 2_576 . . . ? N6 C28 N5 C30 0.2(4) . . . . ? N6 C28 N5 C27' -175.7(7) . . . . ? N6 C28 N5 C27 170.2(5) . . . . ? C29 C30 N5 C28 -0.6(5) . . . . ? C29 C30 N5 C27' 176.4(6) . . . . ? C29 C30 N5 C27 -168.3(6) . . . . ? C24 C27' N5 C28 29.1(11) . . . . ? C24 C27' N5 C30 -146.5(5) . . . . ? C24 C27' N5 C27 63.6(19) . . . . ? C24 C27 N5 C28 70.4(8) . . . . ? C24 C27 N5 C30 -123.1(7) . . . . ? C24 C27 N5 C27' -84(2) . . . . ? N5 C28 N6 C29 0.2(4) . . . . ? N5 C28 N6 Co2 178.9(2) . . . . ? C30 C29 N6 C28 -0.6(5) . . . . ? C30 C29 N6 Co2 -179.2(3) . . . . ? O8 Co2 N6 C28 -90.4(3) . . . . ? O3 Co2 N6 C28 148.1(3) . . . . ? O5 Co2 N6 C28 18.4(3) . . . . ? O8 Co2 N6 C29 88.0(3) . . . . ? O3 Co2 N6 C29 -33.6(4) . . . . ? O5 Co2 N6 C29 -163.2(3) . . . . ? O2 C7 O1 Co1 3.9(2) . . . 2_665 ? C1 C7 O1 Co1 -174.59(17) . . . 2_665 ? O1 C7 O2 Co1 -3.6(2) . . . 2_665 ? C1 C7 O2 Co1 174.90(19) . . . 2_665 ? O4 C8 O3 Co2 -6.1(3) . . . . ? C3 C8 O3 Co2 175.71(15) . . . . ? O8 Co2 O3 C8 -51.4(2) . . . . ? O5 Co2 O3 C8 -173.73(18) . . . . ? N6 Co2 O3 C8 69.8(2) . . . . ? O3 C8 O4 Co1 105.3(3) . . . . ? C3 C8 O4 Co1 -76.6(3) . . . . ? O7 Co1 O4 C8 -90.9(2) . . . . ? N3 Co1 O4 C8 179.6(2) . . . . ? N1 Co1 O4 C8 2.0(2) . . . . ? O1 Co1 O4 C8 89.3(2) 2_665 . . . ? O2 Co1 O4 C8 109.1(3) 2_665 . . . ? O6 C15 O5 Co2 16.4(3) . . . . ? C9 C15 O5 Co2 -161.15(17) . . . . ? O8 Co2 O5 C15 -160.79(17) . . . . ? O3 Co2 O5 C15 -37.9(2) . . . . ? N6 Co2 O5 C15 89.99(19) . . . . ? O8 C16 O7 Co1 23.9(4) . . . . ? C11 C16 O7 Co1 -158.37(16) . . . . ? O4 Co1 O7 C16 8.2(2) . . . . ? N3 Co1 O7 C16 93.4(2) . . . . ? N1 Co1 O7 C16 -83.2(2) . . . . ? O1 Co1 O7 C16 -172.22(18) 2_665 . . . ? O2 Co1 O7 C16 -178.0(2) 2_665 . . . ? O7 C16 O8 Co2 -87.5(3) . . . . ? C11 C16 O8 Co2 94.7(3) . . . . ? O3 Co2 O8 C16 106.2(2) . . . . ? O5 Co2 O8 C16 -122.8(2) . . . . ? N6 Co2 O8 C16 -22.0(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N8 H8A O2 0.82 1.95 2.738(2) 160.4 1_566 N7 H7B O6 0.81 1.86 2.651(2) 165.3 2 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.818 _refine_diff_density_min -0.693 _refine_diff_density_rms 0.059