data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Li, Zuo-Xi' _publ_contact_author_name 'Dr Li, Zuo-Xi' _publ_contact_author_email Lizx@nwu.edu.cn _publ_section_title ; Benzoate Acid-Dependent Formation of a Series of Interpenetrating Metal-Organic Frameworks Based on the Cobalt[?]1,4-Bis(imidazolyl)benzene Coordination Substrate ; # Attachment '- crystallographic data.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 801489' #TrackingRef '- crystallographic data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C58 H0 Co2 N0 O0' _chemical_formula_weight 814.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8571(16) _cell_length_b 10.889(2) _cell_length_c 11.869(2) _cell_angle_alpha 69.57(3) _cell_angle_beta 75.68(3) _cell_angle_gamma 70.86(3) _cell_volume 888.8(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 402 _exptl_absorpt_coefficient_mu 0.977 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 7822 _diffrn_reflns_av_R_equivalents 0.0634 _diffrn_reflns_av_sigmaI/netI 0.0779 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3132 _reflns_number_gt 2581 _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^)+(0.0620P)^2^+3.4625P] 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 3132 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0823 _refine_ls_R_factor_gt 0.0668 _refine_ls_wR_factor_ref 0.1864 _refine_ls_wR_factor_gt 0.1783 _refine_ls_goodness_of_fit_ref 1.168 _refine_ls_restrained_S_all 1.168 _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 0.59716(10) 0.12143(8) 0.65260(7) 0.0222(3) Uani 1 1 d . . . O1 O 0.3262(6) 0.1836(4) 0.6341(4) 0.0330(10) Uani 1 1 d . . . O3 O 0.8097(6) 0.1249(4) 0.7178(4) 0.0333(10) Uani 1 1 d . . . O2 O 0.4454(5) 0.3501(4) 0.6076(4) 0.0306(10) Uani 1 1 d . . . O4 O 0.5789(5) 0.1048(4) 0.8660(4) 0.0334(10) Uani 1 1 d . . . N1 N 0.7072(7) 0.1620(5) 0.4680(4) 0.0272(11) Uani 1 1 d . . . N3 N 0.6966(7) 0.7020(5) -0.1609(4) 0.0283(12) Uani 1 1 d . . . C4 C 0.7452(9) 0.3845(6) 0.1646(5) 0.0289(14) Uani 1 1 d . . . C1 C 0.6664(9) 0.2817(6) 0.3861(5) 0.0297(14) Uani 1 1 d . . . H1A H 0.5847 0.3594 0.4026 0.036 Uiso 1 1 calc R . . N2 N 0.7590(7) 0.2761(5) 0.2755(4) 0.0285(11) Uani 1 1 d . . . C15 C 0.1550(8) 0.5405(6) 0.4844(5) 0.0279(13) Uani 1 1 d . . . H15A H 0.2594 0.5683 0.4737 0.033 Uiso 1 1 calc R . . N4 N 0.6394(7) -0.0904(5) 0.7137(4) 0.0281(11) Uani 1 1 d . . . C14 C 0.1514(7) 0.4086(6) 0.5511(5) 0.0219(12) Uani 1 1 d . . . C17 C 0.7447(8) 0.0994(6) 0.8302(5) 0.0256(13) Uani 1 1 d . . . C20 C 0.8279(8) -0.0221(6) 1.0382(5) 0.0276(13) Uani 1 1 d . . . H20A H 0.7130 -0.0376 1.0639 0.033 Uiso 1 1 calc R . . C9 C 0.7912(12) 0.3560(7) 0.0555(6) 0.051(2) Uani 1 1 d . . . H9A H 0.8316 0.2663 0.0535 0.062 Uiso 1 1 calc R . . C18 C 0.8741(8) 0.0524(6) 0.9194(5) 0.0224(12) Uani 1 1 d . . . C13 C 0.3174(8) 0.3093(6) 0.6024(5) 0.0256(13) Uani 1 1 d . . . C7 C 0.7144(9) 0.5926(6) -0.0503(5) 0.0290(14) Uani 1 1 d . . . C19 C 1.0475(8) 0.0734(6) 0.8814(5) 0.0286(14) Uani 1 1 d . . . H19A H 1.0797 0.1223 0.8014 0.034 Uiso 1 1 calc R . . C5 C 0.6812(12) 0.5160(7) 0.1662(6) 0.050(2) Uani 1 1 d . . . H5A H 0.6472 0.5358 0.2401 0.060 Uiso 1 1 calc R . . C6 C 0.6664(12) 0.6200(7) 0.0592(6) 0.053(2) Uani 1 1 d . . . H6A H 0.6233 0.7097 0.0612 0.064 Uiso 1 1 calc R . . C16 C -0.0052(8) 0.3692(6) 0.5663(5) 0.0287(14) Uani 1 1 d . . . H16A H -0.0093 0.2809 0.6113 0.034 Uiso 1 1 calc R . . C12 C 0.7315(12) 0.6909(7) -0.2763(6) 0.049(2) Uani 1 1 d . . . H12A H 0.7725 0.6110 -0.2986 0.058 Uiso 1 1 calc R . . C3 C 0.8669(10) 0.1456(6) 0.2894(6) 0.0407(17) Uani 1 1 d . . . H3B H 0.9473 0.1114 0.2286 0.049 Uiso 1 1 calc R . . C2 C 0.8346(9) 0.0768(6) 0.4067(6) 0.0363(16) Uani 1 1 d . . . H2A H 0.8896 -0.0144 0.4414 0.044 Uiso 1 1 calc R . . C10 C 0.6945(11) -0.1809(7) 0.6487(6) 0.0464(19) Uani 1 1 d . . . H10A H 0.7052 -0.1579 0.5645 0.056 Uiso 1 1 calc R . . C8 C 0.7774(12) 0.4612(7) -0.0515(6) 0.052(2) Uani 1 1 d . . . H8A H 0.8118 0.4417 -0.1255 0.063 Uiso 1 1 calc R . . C11 C 0.6410(8) 0.8356(6) -0.1719(6) 0.0294(14) Uiso 1 1 d . . . H11A H 0.6076 0.8714 -0.1067 0.035 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 0.0199(4) 0.0215(4) 0.0200(4) 0.0019(3) -0.0088(3) -0.0030(3) O1 0.032(2) 0.020(2) 0.034(2) 0.0044(19) -0.0094(19) 0.0003(18) O3 0.034(2) 0.040(3) 0.024(2) 0.0019(19) -0.0127(18) -0.012(2) O2 0.023(2) 0.035(2) 0.037(2) -0.013(2) -0.0149(18) -0.0013(18) O4 0.021(2) 0.035(2) 0.043(3) -0.011(2) -0.0132(19) -0.0010(18) N1 0.031(3) 0.026(3) 0.020(2) -0.001(2) -0.007(2) -0.007(2) N3 0.043(3) 0.020(3) 0.019(2) 0.000(2) -0.008(2) -0.008(2) C4 0.041(4) 0.020(3) 0.020(3) -0.002(2) -0.006(3) -0.005(3) C1 0.039(4) 0.025(3) 0.018(3) -0.002(3) -0.006(3) -0.003(3) N2 0.036(3) 0.020(3) 0.019(2) 0.000(2) -0.004(2) -0.001(2) C15 0.020(3) 0.030(3) 0.036(3) -0.005(3) -0.009(3) -0.010(2) N4 0.031(3) 0.025(3) 0.026(3) 0.002(2) -0.010(2) -0.009(2) C14 0.017(3) 0.022(3) 0.024(3) -0.005(2) -0.008(2) 0.000(2) C17 0.028(3) 0.018(3) 0.032(3) -0.005(3) -0.013(3) -0.005(2) C20 0.021(3) 0.031(3) 0.029(3) -0.007(3) -0.001(2) -0.008(2) C9 0.098(6) 0.020(3) 0.021(3) -0.006(3) -0.004(4) -0.001(4) C18 0.027(3) 0.020(3) 0.019(3) -0.005(2) -0.006(2) -0.003(2) C13 0.023(3) 0.031(3) 0.017(3) -0.004(3) -0.005(2) -0.002(3) C7 0.042(4) 0.022(3) 0.019(3) 0.000(3) -0.005(3) -0.011(3) C19 0.031(3) 0.035(3) 0.018(3) -0.003(3) -0.004(2) -0.011(3) C5 0.091(6) 0.025(4) 0.021(3) -0.007(3) -0.002(4) -0.004(4) C6 0.106(7) 0.017(3) 0.025(4) -0.004(3) -0.009(4) -0.004(4) C16 0.029(3) 0.018(3) 0.031(3) 0.003(3) -0.008(3) -0.003(2) C12 0.098(6) 0.024(3) 0.025(3) -0.004(3) -0.014(4) -0.018(4) C3 0.048(4) 0.027(3) 0.028(3) -0.006(3) 0.002(3) 0.006(3) C2 0.041(4) 0.025(3) 0.029(3) -0.001(3) -0.006(3) 0.001(3) C10 0.087(6) 0.033(4) 0.024(3) -0.001(3) -0.017(4) -0.023(4) C8 0.098(7) 0.027(4) 0.018(3) -0.006(3) -0.005(4) -0.002(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 O3 2.023(4) . ? Co1 O1 2.054(4) . ? Co1 N1 2.093(5) . ? Co1 N4 2.099(5) . ? Co1 O2 2.312(4) . ? O1 C13 1.270(7) . ? O3 C17 1.271(7) . ? O2 C13 1.246(7) . ? O4 C17 1.255(7) . ? N1 C1 1.320(7) . ? N1 C2 1.376(8) . ? N3 C11 1.342(8) . ? N3 C12 1.369(8) . ? N3 C7 1.432(7) . ? C4 C5 1.358(9) . ? C4 C9 1.371(9) . ? C4 N2 1.429(7) . ? C1 N2 1.345(8) . ? C1 H1A 0.9300 . ? N2 C3 1.371(8) . ? C15 C16 1.376(8) 2_566 ? C15 C14 1.383(8) . ? C15 H15A 0.9300 . ? N4 C11 1.315(7) 1_546 ? N4 C10 1.357(9) . ? C14 C16 1.382(8) . ? C14 C13 1.500(7) . ? C17 C18 1.493(8) . ? C20 C19 1.383(8) 2_757 ? C20 C18 1.385(8) . ? C20 H20A 0.9300 . ? C9 C8 1.381(9) . ? C9 H9A 0.9300 . ? C18 C19 1.393(8) . ? C7 C8 1.356(9) . ? C7 C6 1.369(9) . ? C19 C20 1.383(8) 2_757 ? C19 H19A 0.9300 . ? C5 C6 1.376(9) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C16 C15 1.376(8) 2_566 ? C16 H16A 0.9300 . ? C12 C10 1.349(9) 1_564 ? C12 H12A 0.9300 . ? C3 C2 1.336(9) . ? C3 H3B 0.9300 . ? C2 H2A 0.9300 . ? C10 C12 1.349(9) 1_546 ? C10 H10A 0.9300 . ? C8 H8A 0.9300 . ? C11 N4 1.315(7) 1_564 ? C11 H11A 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 O3 Co1 O1 152.13(19) . . ? O3 Co1 N1 98.57(18) . . ? O1 Co1 N1 98.33(18) . . ? O3 Co1 N4 96.52(18) . . ? O1 Co1 N4 100.62(18) . . ? N1 Co1 N4 104.2(2) . . ? O3 Co1 O2 99.16(17) . . ? O1 Co1 O2 60.10(16) . . ? N1 Co1 O2 86.25(18) . . ? N4 Co1 O2 159.65(17) . . ? C13 O1 Co1 94.3(4) . . ? C17 O3 Co1 99.1(4) . . ? C13 O2 Co1 83.2(3) . . ? C1 N1 C2 105.8(5) . . ? C1 N1 Co1 124.7(4) . . ? C2 N1 Co1 129.5(4) . . ? C11 N3 C12 106.4(5) . . ? C11 N3 C7 126.9(5) . . ? C12 N3 C7 126.7(5) . . ? C5 C4 C9 119.5(6) . . ? C5 C4 N2 120.6(5) . . ? C9 C4 N2 119.9(5) . . ? N1 C1 N2 110.9(5) . . ? N1 C1 H1A 124.5 . . ? N2 C1 H1A 124.5 . . ? C1 N2 C3 106.8(5) . . ? C1 N2 C4 126.6(5) . . ? C3 N2 C4 126.6(5) . . ? C16 C15 C14 120.4(5) 2_566 . ? C16 C15 H15A 119.8 2_566 . ? C14 C15 H15A 119.8 . . ? C11 N4 C10 105.4(5) 1_546 . ? C11 N4 Co1 124.6(4) 1_546 . ? C10 N4 Co1 129.4(4) . . ? C16 C14 C15 119.0(5) . . ? C16 C14 C13 120.9(5) . . ? C15 C14 C13 120.1(5) . . ? O4 C17 O3 121.3(5) . . ? O4 C17 C18 120.6(5) . . ? O3 C17 C18 117.9(5) . . ? C19 C20 C18 120.1(5) 2_757 . ? C19 C20 H20A 119.9 2_757 . ? C18 C20 H20A 119.9 . . ? C4 C9 C8 119.7(6) . . ? C4 C9 H9A 120.2 . . ? C8 C9 H9A 120.2 . . ? C20 C18 C19 119.4(5) . . ? C20 C18 C17 120.1(5) . . ? C19 C18 C17 120.2(5) . . ? O2 C13 O1 121.7(5) . . ? O2 C13 C14 120.4(5) . . ? O1 C13 C14 117.8(5) . . ? C8 C7 C6 118.9(6) . . ? C8 C7 N3 121.3(5) . . ? C6 C7 N3 119.9(5) . . ? C20 C19 C18 120.4(5) 2_757 . ? C20 C19 H19A 119.8 2_757 . ? C18 C19 H19A 119.8 . . ? C4 C5 C6 120.4(6) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C7 C6 C5 120.6(6) . . ? C7 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? C15 C16 C14 120.7(5) 2_566 . ? C15 C16 H16A 119.7 2_566 . ? C14 C16 H16A 119.7 . . ? C10 C12 N3 106.2(6) 1_564 . ? C10 C12 H12A 126.9 1_564 . ? N3 C12 H12A 126.9 . . ? C2 C3 N2 107.0(6) . . ? C2 C3 H3B 126.5 . . ? N2 C3 H3B 126.5 . . ? C3 C2 N1 109.4(5) . . ? C3 C2 H2A 125.3 . . ? N1 C2 H2A 125.3 . . ? C12 C10 N4 110.2(6) 1_546 . ? C12 C10 H10A 124.9 1_546 . ? N4 C10 H10A 124.9 . . ? C7 C8 C9 121.0(6) . . ? C7 C8 H8A 119.5 . . ? C9 C8 H8A 119.5 . . ? N4 C11 N3 111.8(5) 1_564 . ? N4 C11 H11A 124.1 1_564 . ? N3 C11 H11A 124.1 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.767 _refine_diff_density_min -0.641 _refine_diff_density_rms 0.132 data_2 _database_code_depnum_ccdc_archive 'CCDC 801490' #TrackingRef '- crystallographic data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H34 Co3 N8 O16' _chemical_formula_weight 1083.56 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.028(5) _cell_length_b 10.493(2) _cell_length_c 17.871(4) _cell_angle_alpha 90.00 _cell_angle_beta 120.32(3) _cell_angle_gamma 90.00 _cell_volume 4374.8(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 21276 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2204 _exptl_absorpt_coefficient_mu 1.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.747 _exptl_absorpt_correction_T_max 0.785 _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 'CCD area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18623 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3867 _reflns_number_gt 3577 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _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^)+(0.0284P)^2^+6.6713P] 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 3867 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0711 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.126 _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 O5 O 0.20451(7) -0.22897(16) 0.21129(10) 0.0355(4) Uani 1 1 d . . . C21 C 0.23284(10) -0.1667(2) 0.28072(14) 0.0285(5) Uani 1 1 d . . . Co1 Co 0.0000 -0.48432(4) 0.2500 0.02389(11) Uani 1 2 d S . . Co2 Co 0.243673(13) 0.17974(3) 0.645327(18) 0.02525(10) Uani 1 1 d . . . N4 N 0.50876(8) 0.90838(18) 1.16404(12) 0.0302(4) Uani 1 1 d . . . C12 C 0.55245(11) 0.9218(3) 1.14569(17) 0.0439(7) Uani 1 1 d . . . H12 H 0.5841 0.9749 1.1752 0.053 Uiso 1 1 calc R . . O1 O 0.21738(7) -0.00137(15) 0.59784(10) 0.0334(4) Uani 1 1 d . . . O1W O 0.18781(7) 0.28441(16) 0.53774(10) 0.0338(4) Uani 1 1 d . . . O2 O 0.26956(7) 0.09116(15) 0.55186(10) 0.0348(4) Uani 1 1 d . . . O3 O 0.06992(7) -0.38722(18) 0.29359(10) 0.0429(4) Uani 1 1 d . . . O6 O 0.27502(8) -0.10129(18) 0.29454(11) 0.0450(5) Uani 1 1 d . . . N1 N 0.31648(8) 0.28848(19) 0.70036(12) 0.0323(4) Uani 1 1 d . . . C7 C 0.46384(10) 0.6933(2) 0.98595(15) 0.0309(5) Uani 1 1 d . . . C14 C 0.17109(9) -0.1758(2) 0.45912(13) 0.0254(5) Uani 1 1 d . . . H14 H 0.1579 -0.1786 0.4981 0.030 Uiso 1 1 calc R . . C18 C 0.23525(9) -0.0905(2) 0.41613(13) 0.0254(5) Uani 1 1 d . . . H18 H 0.2647 -0.0350 0.4256 0.031 Uiso 1 1 calc R . . C16 C 0.16807(9) -0.2536(2) 0.33059(13) 0.0262(5) Uani 1 1 d . . . H16 H 0.1522 -0.3073 0.2826 0.031 Uiso 1 1 calc R . . N2 N 0.38132(8) 0.42746(19) 0.78638(12) 0.0326(4) Uani 1 1 d . . . O4 O 0.08325(8) -0.35372(18) 0.42536(11) 0.0455(5) Uani 1 1 d . . . N3 N 0.49154(8) 0.78463(18) 1.05444(12) 0.0317(4) Uani 1 1 d . . . C15 C 0.14718(9) -0.2559(2) 0.38756(13) 0.0250(5) Uani 1 1 d . . . C20 C 0.09689(10) -0.3385(2) 0.36954(14) 0.0294(5) Uani 1 1 d . . . C13 C 0.21458(9) -0.0914(2) 0.47314(13) 0.0242(4) Uani 1 1 d . . . C19 C 0.23591(9) 0.0036(2) 0.54558(13) 0.0266(5) Uani 1 1 d . . . C17 C 0.21242(9) -0.1719(2) 0.34493(13) 0.0249(5) Uani 1 1 d . . . C4 C 0.41065(9) 0.5178(2) 0.85504(14) 0.0298(5) Uani 1 1 d . . . C1 C 0.33260(10) 0.3657(2) 0.76685(14) 0.0313(5) Uani 1 1 d . . . H1 H 0.3128 0.3763 0.7965 0.038 Uiso 1 1 calc R . . C9 C 0.40878(11) 0.5030(2) 0.93018(15) 0.0367(6) Uani 1 1 d . . . H9 H 0.3897 0.4338 0.9365 0.044 Uiso 1 1 calc R . . C10 C 0.47307(10) 0.8253(2) 1.10742(15) 0.0329(5) Uani 1 1 d . . . H10 H 0.4394 0.7982 1.1044 0.039 Uiso 1 1 calc R . . C8 C 0.43534(11) 0.5914(2) 0.99599(16) 0.0376(6) Uani 1 1 d . . . H8 H 0.4341 0.5824 1.0468 0.045 Uiso 1 1 calc R . . C5 C 0.43972(10) 0.6189(2) 0.84546(15) 0.0357(6) Uani 1 1 d . . . H5 H 0.4413 0.6274 0.7949 0.043 Uiso 1 1 calc R . . C6 C 0.46654(11) 0.7076(2) 0.91139(15) 0.0367(6) Uani 1 1 d . . . H6 H 0.4862 0.7760 0.9055 0.044 Uiso 1 1 calc R . . C3 C 0.39667(12) 0.3870(3) 0.72816(18) 0.0529(8) Uani 1 1 d . . . H3 H 0.4286 0.4127 0.7253 0.064 Uiso 1 1 calc R . . C2 C 0.35666(12) 0.3029(3) 0.67598(18) 0.0503(8) Uani 1 1 d . . . H2 H 0.3563 0.2606 0.6300 0.060 Uiso 1 1 calc R . . C11 C 0.54198(12) 0.8463(3) 1.07859(18) 0.0468(7) Uani 1 1 d . . . H11 H 0.5647 0.8377 1.0534 0.056 Uiso 1 1 calc R . . O2W O 0.13524(8) 0.4732(2) 0.56848(13) 0.0565(5) Uani 1 1 d . . . H1A H 0.1686 0.3396 0.5472 0.085 Uiso 1 1 d R . . H1B H 0.2032 0.3224 0.5125 0.085 Uiso 1 1 d R . . H2A H 0.1478 0.4370 0.6173 0.085 Uiso 1 1 d R . . H2B H 0.1243 0.5276 0.5279 0.085 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 O5 0.0468(10) 0.0441(10) 0.0242(8) -0.0058(7) 0.0243(8) -0.0064(8) C21 0.0394(13) 0.0269(11) 0.0278(12) 0.0023(9) 0.0233(11) 0.0024(10) Co1 0.0267(2) 0.0232(2) 0.0230(2) 0.000 0.01346(18) 0.000 Co2 0.03234(17) 0.02661(17) 0.02121(16) -0.00647(12) 0.01676(13) -0.00611(12) N4 0.0307(10) 0.0307(10) 0.0313(10) -0.0066(8) 0.0172(9) -0.0024(8) C12 0.0423(14) 0.0485(16) 0.0508(16) -0.0252(13) 0.0310(13) -0.0225(12) O1 0.0491(10) 0.0324(9) 0.0309(8) -0.0109(7) 0.0292(8) -0.0100(7) O1W 0.0405(9) 0.0377(9) 0.0277(8) 0.0004(7) 0.0206(8) -0.0013(7) O2 0.0426(9) 0.0351(9) 0.0361(9) -0.0156(7) 0.0268(8) -0.0161(8) O3 0.0459(10) 0.0538(11) 0.0330(9) -0.0164(8) 0.0228(8) -0.0254(9) O6 0.0576(11) 0.0484(11) 0.0480(11) -0.0122(9) 0.0406(10) -0.0182(9) N1 0.0329(10) 0.0364(11) 0.0279(10) -0.0099(8) 0.0155(9) -0.0069(9) C7 0.0287(12) 0.0321(12) 0.0305(12) -0.0093(10) 0.0140(10) -0.0039(10) C14 0.0320(12) 0.0281(11) 0.0234(11) -0.0032(9) 0.0193(10) -0.0014(9) C18 0.0299(11) 0.0236(11) 0.0280(11) -0.0036(9) 0.0185(10) -0.0031(9) C16 0.0331(12) 0.0264(11) 0.0197(10) -0.0040(9) 0.0138(9) -0.0019(9) N2 0.0303(10) 0.0390(11) 0.0279(10) -0.0105(9) 0.0143(9) -0.0078(9) O4 0.0520(11) 0.0569(12) 0.0436(10) -0.0111(9) 0.0358(9) -0.0206(9) N3 0.0325(10) 0.0335(11) 0.0333(10) -0.0120(8) 0.0198(9) -0.0088(8) C15 0.0294(11) 0.0260(11) 0.0224(11) -0.0022(9) 0.0151(9) -0.0028(9) C20 0.0325(12) 0.0284(12) 0.0290(12) -0.0042(10) 0.0169(10) -0.0044(10) C13 0.0292(11) 0.0233(11) 0.0221(11) -0.0044(9) 0.0144(9) -0.0024(9) C19 0.0314(12) 0.0266(11) 0.0235(11) -0.0044(9) 0.0152(10) -0.0016(9) C17 0.0317(11) 0.0258(11) 0.0230(11) 0.0003(9) 0.0180(9) 0.0011(9) C4 0.0251(11) 0.0325(12) 0.0270(11) -0.0072(9) 0.0095(10) -0.0025(9) C1 0.0315(12) 0.0344(13) 0.0290(12) -0.0060(10) 0.0160(10) -0.0055(10) C9 0.0407(14) 0.0384(14) 0.0379(13) -0.0107(11) 0.0248(12) -0.0158(11) C10 0.0288(12) 0.0369(13) 0.0374(13) -0.0107(11) 0.0201(11) -0.0065(10) C8 0.0441(14) 0.0441(15) 0.0323(13) -0.0108(11) 0.0250(12) -0.0150(12) C5 0.0416(14) 0.0406(14) 0.0249(12) -0.0029(10) 0.0167(11) -0.0070(11) C6 0.0438(14) 0.0339(13) 0.0335(13) -0.0030(10) 0.0202(12) -0.0111(11) C3 0.0416(15) 0.078(2) 0.0507(16) -0.0308(15) 0.0320(14) -0.0245(15) C2 0.0455(15) 0.071(2) 0.0453(16) -0.0327(14) 0.0310(14) -0.0216(14) C11 0.0473(15) 0.0541(17) 0.0567(17) -0.0279(14) 0.0395(14) -0.0260(13) O2W 0.0514(12) 0.0612(13) 0.0624(13) -0.0014(10) 0.0328(11) 0.0111(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O5 C21 1.262(3) . ? O5 Co2 2.0090(16) 6 ? C21 O6 1.244(3) . ? C21 C17 1.505(3) . ? Co1 O3 1.9312(17) . ? Co1 O3 1.9312(17) 2 ? Co1 N4 2.0126(18) 3_434 ? Co1 N4 2.0126(18) 4_536 ? Co2 O5 2.0090(16) 6_556 ? Co2 N1 2.046(2) . ? Co2 O1 2.0561(16) . ? Co2 O1W 2.0619(18) . ? Co2 O2 2.3072(15) . ? Co2 C19 2.502(2) . ? N4 C10 1.315(3) . ? N4 C12 1.383(3) . ? N4 Co1 2.0126(18) 3_566 ? C12 C11 1.343(3) . ? C12 H12 0.9300 . ? O1 C19 1.264(3) . ? O1W H1A 0.8497 . ? O1W H1B 0.8499 . ? O2 C19 1.257(3) . ? O3 C20 1.279(3) . ? N1 C1 1.318(3) . ? N1 C2 1.367(3) . ? C7 C6 1.379(3) . ? C7 C8 1.381(3) . ? C7 N3 1.433(3) . ? C14 C15 1.388(3) . ? C14 C13 1.390(3) . ? C14 H14 0.9300 . ? C18 C13 1.388(3) . ? C18 C17 1.391(3) . ? C18 H18 0.9300 . ? C16 C17 1.389(3) . ? C16 C15 1.391(3) . ? C16 H16 0.9300 . ? N2 C1 1.346(3) . ? N2 C3 1.368(3) . ? N2 C4 1.432(3) . ? O4 C20 1.236(3) . ? N3 C10 1.344(3) . ? N3 C11 1.368(3) . ? C15 C20 1.504(3) . ? C13 C19 1.499(3) . ? C4 C9 1.378(3) . ? C4 C5 1.381(3) . ? C1 H1 0.9300 . ? C9 C8 1.381(3) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C8 H8 0.9300 . ? C5 C6 1.384(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C3 C2 1.341(4) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? C11 H11 0.9300 . ? O2W H2A 0.8501 . ? O2W H2B 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 O5 Co2 101.87(14) . 6 ? O6 C21 O5 121.4(2) . . ? O6 C21 C17 121.4(2) . . ? O5 C21 C17 117.2(2) . . ? O3 Co1 O3 116.31(12) . 2 ? O3 Co1 N4 97.74(8) . 3_434 ? O3 Co1 N4 117.10(8) 2 3_434 ? O3 Co1 N4 117.10(8) . 4_536 ? O3 Co1 N4 97.74(8) 2 4_536 ? N4 Co1 N4 111.97(11) 3_434 4_536 ? O5 Co2 N1 103.79(8) 6_556 . ? O5 Co2 O1 107.76(7) 6_556 . ? N1 Co2 O1 139.63(7) . . ? O5 Co2 O1W 93.18(7) 6_556 . ? N1 Co2 O1W 103.00(8) . . ? O1 Co2 O1W 99.77(7) . . ? O5 Co2 O2 166.04(6) 6_556 . ? N1 Co2 O2 90.17(7) . . ? O1 Co2 O2 59.79(6) . . ? O1W Co2 O2 83.48(6) . . ? O5 Co2 C19 136.76(7) 6_556 . ? N1 Co2 C19 117.95(8) . . ? O1 Co2 C19 30.24(6) . . ? O1W Co2 C19 88.32(7) . . ? O2 Co2 C19 29.96(6) . . ? C10 N4 C12 105.53(19) . . ? C10 N4 Co1 129.42(16) . 3_566 ? C12 N4 Co1 124.56(16) . 3_566 ? C11 C12 N4 109.3(2) . . ? C11 C12 H12 125.3 . . ? N4 C12 H12 125.3 . . ? C19 O1 Co2 94.78(13) . . ? Co2 O1W H1A 114.2 . . ? Co2 O1W H1B 114.8 . . ? H1A O1W H1B 107.2 . . ? C19 O2 Co2 83.62(12) . . ? C20 O3 Co1 123.80(15) . . ? C1 N1 C2 105.4(2) . . ? C1 N1 Co2 125.21(16) . . ? C2 N1 Co2 129.36(16) . . ? C6 C7 C8 121.0(2) . . ? C6 C7 N3 119.5(2) . . ? C8 C7 N3 119.5(2) . . ? C15 C14 C13 120.68(19) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C13 C18 C17 120.69(19) . . ? C13 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C17 C16 C15 120.46(19) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C1 N2 C3 106.62(19) . . ? C1 N2 C4 125.93(19) . . ? C3 N2 C4 127.4(2) . . ? C10 N3 C11 107.04(19) . . ? C10 N3 C7 126.51(19) . . ? C11 N3 C7 126.45(19) . . ? C14 C15 C16 119.4(2) . . ? C14 C15 C20 119.78(18) . . ? C16 C15 C20 120.67(19) . . ? O4 C20 O3 124.2(2) . . ? O4 C20 C15 120.5(2) . . ? O3 C20 C15 115.28(19) . . ? C18 C13 C14 119.29(19) . . ? C18 C13 C19 120.51(19) . . ? C14 C13 C19 120.06(18) . . ? O2 C19 O1 120.19(19) . . ? O2 C19 C13 120.56(18) . . ? O1 C19 C13 119.16(19) . . ? O2 C19 Co2 66.42(11) . . ? O1 C19 Co2 54.98(10) . . ? C13 C19 Co2 164.48(16) . . ? C16 C17 C18 119.40(19) . . ? C16 C17 C21 119.77(19) . . ? C18 C17 C21 120.73(19) . . ? C9 C4 C5 120.7(2) . . ? C9 C4 N2 118.9(2) . . ? C5 C4 N2 120.4(2) . . ? N1 C1 N2 111.4(2) . . ? N1 C1 H1 124.3 . . ? N2 C1 H1 124.3 . . ? C4 C9 C8 119.7(2) . . ? C4 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? N4 C10 N3 111.3(2) . . ? N4 C10 H10 124.3 . . ? N3 C10 H10 124.3 . . ? C9 C8 C7 119.6(2) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C4 C5 C6 119.8(2) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 119.3(2) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C2 C3 N2 106.6(2) . . ? C2 C3 H3 126.7 . . ? N2 C3 H3 126.7 . . ? C3 C2 N1 110.0(2) . . ? C3 C2 H2 125.0 . . ? N1 C2 H2 125.0 . . ? C12 C11 N3 106.7(2) . . ? C12 C11 H11 126.6 . . ? N3 C11 H11 126.6 . . ? H2A O2W H2B 164.4 . . ? 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 Co2 O5 C21 O6 -3.0(3) 6 . . . ? Co2 O5 C21 C17 175.25(16) 6 . . . ? C10 N4 C12 C11 -0.1(3) . . . . ? Co1 N4 C12 C11 -172.75(19) 3_566 . . . ? O5 Co2 O1 C19 165.80(13) 6_556 . . . ? N1 Co2 O1 C19 -54.47(18) . . . . ? O1W Co2 O1 C19 69.24(14) . . . . ? O2 Co2 O1 C19 -7.26(12) . . . . ? O5 Co2 O2 C19 -21.2(3) 6_556 . . . ? N1 Co2 O2 C19 158.94(14) . . . . ? O1 Co2 O2 C19 7.32(13) . . . . ? O1W Co2 O2 C19 -97.99(14) . . . . ? O3 Co1 O3 C20 81.37(19) 2 . . . ? N4 Co1 O3 C20 -153.2(2) 3_434 . . . ? N4 Co1 O3 C20 -33.6(2) 4_536 . . . ? O5 Co2 N1 C1 3.3(2) 6_556 . . . ? O1 Co2 N1 C1 -137.41(18) . . . . ? O1W Co2 N1 C1 99.9(2) . . . . ? O2 Co2 N1 C1 -176.8(2) . . . . ? C19 Co2 N1 C1 -165.05(18) . . . . ? O5 Co2 N1 C2 -173.3(2) 6_556 . . . ? O1 Co2 N1 C2 46.0(3) . . . . ? O1W Co2 N1 C2 -76.7(2) . . . . ? O2 Co2 N1 C2 6.6(2) . . . . ? C19 Co2 N1 C2 18.4(3) . . . . ? C6 C7 N3 C10 145.0(3) . . . . ? C8 C7 N3 C10 -35.7(4) . . . . ? C6 C7 N3 C11 -35.4(4) . . . . ? C8 C7 N3 C11 143.9(3) . . . . ? C13 C14 C15 C16 1.6(3) . . . . ? C13 C14 C15 C20 -174.9(2) . . . . ? C17 C16 C15 C14 -0.1(3) . . . . ? C17 C16 C15 C20 176.3(2) . . . . ? Co1 O3 C20 O4 4.2(4) . . . . ? Co1 O3 C20 C15 -174.31(15) . . . . ? C14 C15 C20 O4 -13.4(3) . . . . ? C16 C15 C20 O4 170.2(2) . . . . ? C14 C15 C20 O3 165.2(2) . . . . ? C16 C15 C20 O3 -11.2(3) . . . . ? C17 C18 C13 C14 0.8(3) . . . . ? C17 C18 C13 C19 -175.0(2) . . . . ? C15 C14 C13 C18 -1.9(3) . . . . ? C15 C14 C13 C19 173.9(2) . . . . ? Co2 O2 C19 O1 -12.0(2) . . . . ? Co2 O2 C19 C13 164.40(19) . . . . ? Co2 O1 C19 O2 13.4(2) . . . . ? Co2 O1 C19 C13 -163.00(17) . . . . ? C18 C13 C19 O2 5.3(3) . . . . ? C14 C13 C19 O2 -170.4(2) . . . . ? C18 C13 C19 O1 -178.3(2) . . . . ? C14 C13 C19 O1 6.0(3) . . . . ? C18 C13 C19 Co2 118.3(5) . . . . ? C14 C13 C19 Co2 -57.5(6) . . . . ? O5 Co2 C19 O2 172.69(12) 6_556 . . . ? N1 Co2 C19 O2 -24.00(16) . . . . ? O1 Co2 C19 O2 -167.4(2) . . . . ? O1W Co2 C19 O2 79.84(13) . . . . ? O5 Co2 C19 O1 -19.94(18) 6_556 . . . ? N1 Co2 C19 O1 143.37(13) . . . . ? O1W Co2 C19 O1 -112.79(14) . . . . ? O2 Co2 C19 O1 167.4(2) . . . . ? O5 Co2 C19 C13 52.6(6) 6_556 . . . ? N1 Co2 C19 C13 -144.1(6) . . . . ? O1 Co2 C19 C13 72.6(6) . . . . ? O1W Co2 C19 C13 -40.2(6) . . . . ? O2 Co2 C19 C13 -120.1(6) . . . . ? C15 C16 C17 C18 -1.0(3) . . . . ? C15 C16 C17 C21 -177.5(2) . . . . ? C13 C18 C17 C16 0.7(3) . . . . ? C13 C18 C17 C21 177.1(2) . . . . ? O6 C21 C17 C16 -174.9(2) . . . . ? O5 C21 C17 C16 6.8(3) . . . . ? O6 C21 C17 C18 8.7(3) . . . . ? O5 C21 C17 C18 -169.6(2) . . . . ? C1 N2 C4 C9 32.5(3) . . . . ? C3 N2 C4 C9 -147.6(3) . . . . ? C1 N2 C4 C5 -146.7(2) . . . . ? C3 N2 C4 C5 33.2(4) . . . . ? C2 N1 C1 N2 -0.6(3) . . . . ? Co2 N1 C1 N2 -177.88(15) . . . . ? C3 N2 C1 N1 0.4(3) . . . . ? C4 N2 C1 N1 -179.7(2) . . . . ? C5 C4 C9 C8 1.2(4) . . . . ? N2 C4 C9 C8 -178.0(2) . . . . ? C12 N4 C10 N3 0.3(3) . . . . ? Co1 N4 C10 N3 172.46(16) 3_566 . . . ? C11 N3 C10 N4 -0.4(3) . . . . ? C7 N3 C10 N4 179.3(2) . . . . ? C4 C9 C8 C7 -0.4(4) . . . . ? C6 C7 C8 C9 -0.5(4) . . . . ? N3 C7 C8 C9 -179.8(2) . . . . ? C9 C4 C5 C6 -1.0(4) . . . . ? N2 C4 C5 C6 178.2(2) . . . . ? C8 C7 C6 C5 0.7(4) . . . . ? N3 C7 C6 C5 180.0(2) . . . . ? C4 C5 C6 C7 0.1(4) . . . . ? C1 N2 C3 C2 0.1(3) . . . . ? C4 N2 C3 C2 -179.8(3) . . . . ? N2 C3 C2 N1 -0.5(4) . . . . ? C1 N1 C2 C3 0.7(3) . . . . ? Co2 N1 C2 C3 177.8(2) . . . . ? N4 C12 C11 N3 -0.1(3) . . . . ? C10 N3 C11 C12 0.3(3) . . . . ? C7 N3 C11 C12 -179.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.342 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.048 data_3 _database_code_depnum_ccdc_archive 'CCDC 801491' #TrackingRef '- crystallographic data.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H13 Co N4 O5' _chemical_formula_weight 412.24 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 9.5455(19) _cell_length_b 10.271(2) _cell_length_c 10.628(2) _cell_angle_alpha 62.03(3) _cell_angle_beta 68.68(3) _cell_angle_gamma 83.38(3) _cell_volume 855.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12849 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 28.2 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 1.042 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.795 _exptl_absorpt_correction_T_max 0.829 _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 'CCD area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7317 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3019 _reflns_number_gt 2517 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _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^)+(0.0425P)^2^+0.2545P] 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 3019 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.0953 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.61763(4) -0.00751(4) 0.22461(4) 0.01745(14) Uani 1 1 d . . . O2 O 0.9182(2) 0.0004(2) 0.1891(2) 0.0298(5) Uani 1 1 d . . . O3 O 0.5971(2) -0.0193(2) 0.6946(2) 0.0276(5) Uani 1 1 d . . . O1 O 0.7021(2) -0.0029(3) 0.3633(2) 0.0306(6) Uani 1 1 d . . . O4 O 0.6602(2) 0.2037(2) 0.4949(3) 0.0340(6) Uani 1 1 d . . . N3 N 0.6736(3) 0.1769(3) 0.0248(3) 0.0289(7) Uani 1 1 d . . . C17 C 0.6898(3) 0.0792(3) 0.5716(3) 0.0212(7) Uani 1 1 d . . . N1 N 0.6600(3) -0.1924(3) 0.2018(3) 0.0286(6) Uani 1 1 d . . . C13 C 0.8494(3) 0.0344(3) 0.5313(3) 0.0192(7) Uani 1 1 d . . . C14 C 0.9228(3) 0.0045(3) 0.4089(3) 0.0188(7) Uani 1 1 d . . . C16 C 0.8455(3) 0.0018(3) 0.3110(3) 0.0216(7) Uani 1 1 d . . . N4 N 0.7885(3) 0.3514(3) -0.2057(3) 0.0318(7) Uani 1 1 d . . . C10 C 0.8965(4) 0.4269(4) -0.3550(4) 0.0305(8) Uani 1 1 d . . . C1 C 0.7789(4) -0.2191(4) 0.1075(4) 0.0305(8) Uani 1 1 d . . . H1 H 0.8533 -0.1479 0.0265 0.037 Uiso 1 1 calc R . . N2 N 0.7784(3) -0.3622(3) 0.1437(3) 0.0375(8) Uani 1 1 d . . . C6 C 0.9281(5) -0.5705(4) 0.1552(4) 0.0601(14) Uani 1 1 d . . . H6 H 0.8790 -0.6193 0.2601 0.072 Uiso 1 1 calc R . . C7 C 0.7928(4) 0.2144(3) -0.0993(3) 0.0289(8) Uani 1 1 d . . . H7 H 0.8708 0.1533 -0.1118 0.035 Uiso 1 1 calc R . . C3 C 0.6530(5) -0.4317(4) 0.2695(5) 0.0635(15) Uani 1 1 d . . . H3 H 0.6239 -0.5320 0.3214 0.076 Uiso 1 1 calc R . . C9 C 0.6570(5) 0.4039(4) -0.1437(4) 0.0607(14) Uani 1 1 d . . . H9 H 0.6223 0.4965 -0.1905 0.073 Uiso 1 1 calc R . . C5 C 0.9614(5) -0.3632(4) -0.0828(4) 0.0565(13) Uani 1 1 d . . . H5 H 0.9342 -0.2699 -0.1396 0.068 Uiso 1 1 calc R . . C2 C 0.5801(4) -0.3256(4) 0.3031(5) 0.0508(12) Uani 1 1 d . . . H2 H 0.4895 -0.3404 0.3828 0.061 Uiso 1 1 calc R . . C8 C 0.5885(5) 0.2970(4) -0.0038(4) 0.0561(13) Uani 1 1 d . . . H8 H 0.4966 0.3030 0.0642 0.067 Uiso 1 1 calc R . . C4 C 0.8921(4) -0.4332(4) 0.0707(4) 0.0390(9) Uani 1 1 d . . . C12 C 0.8582(4) 0.5502(4) -0.4626(4) 0.0424(10) Uani 1 1 d . . . H12 H 0.7624 0.5844 -0.4381 0.051 Uiso 1 1 calc R . . C11 C 1.0367(4) 0.3770(4) -0.3925(4) 0.0411(10) Uani 1 1 d . . . H11 H 1.0619 0.2929 -0.3195 0.049 Uiso 1 1 calc R . . O1W O 0.4508(3) 0.2776(3) 0.3445(3) 0.0477(7) Uani 1 1 d . . . C15 C 0.9283(3) 0.0292(3) 0.6195(3) 0.0217(7) Uani 1 1 d . . . H15 H 0.8792 0.0491 0.7012 0.026 Uiso 1 1 calc R . . H1A H 0.5138 0.2413 0.3900 0.033 Uiso 1 1 d R . . H1B H 0.3873 0.2028 0.3944 0.033 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 0.0152(2) 0.0186(2) 0.0156(2) -0.00753(17) -0.00310(16) 0.00199(16) O2 0.0269(13) 0.0443(15) 0.0224(12) -0.0194(11) -0.0086(10) 0.0055(10) O3 0.0131(11) 0.0350(14) 0.0259(12) -0.0115(11) -0.0015(9) 0.0028(10) O1 0.0177(12) 0.0506(16) 0.0272(13) -0.0198(12) -0.0089(10) 0.0007(10) O4 0.0277(13) 0.0292(14) 0.0377(14) -0.0121(11) -0.0109(11) 0.0119(11) N3 0.0267(15) 0.0269(16) 0.0179(14) -0.0034(12) -0.0029(12) 0.0070(12) C17 0.0159(16) 0.0291(19) 0.0246(17) -0.0183(16) -0.0064(13) 0.0044(14) N1 0.0247(15) 0.0243(15) 0.0313(16) -0.0157(13) 0.0002(12) 0.0000(12) C13 0.0141(15) 0.0210(17) 0.0189(16) -0.0080(13) -0.0036(12) 0.0004(12) C14 0.0132(15) 0.0203(16) 0.0178(16) -0.0063(13) -0.0029(12) -0.0004(12) C16 0.0190(17) 0.0188(17) 0.0220(17) -0.0051(14) -0.0077(13) 0.0007(13) N4 0.0327(17) 0.0235(16) 0.0196(14) -0.0024(12) -0.0001(12) 0.0058(12) C10 0.032(2) 0.0248(18) 0.0198(17) -0.0044(14) -0.0015(14) 0.0019(15) C1 0.033(2) 0.0206(18) 0.0276(19) -0.0116(15) 0.0020(15) -0.0003(14) N2 0.0385(18) 0.0253(16) 0.0335(17) -0.0175(14) 0.0095(13) -0.0010(13) C6 0.078(3) 0.032(2) 0.032(2) -0.0100(18) 0.014(2) 0.010(2) C7 0.0272(18) 0.0246(19) 0.0220(18) -0.0060(15) -0.0025(14) 0.0048(14) C3 0.058(3) 0.031(2) 0.066(3) -0.029(2) 0.031(2) -0.017(2) C9 0.056(3) 0.039(2) 0.037(2) 0.0010(19) 0.006(2) 0.025(2) C5 0.072(3) 0.026(2) 0.039(2) -0.0114(19) 0.007(2) 0.012(2) C2 0.040(2) 0.034(2) 0.053(3) -0.026(2) 0.0220(19) -0.0118(18) C8 0.044(2) 0.048(3) 0.030(2) -0.0006(19) 0.0067(18) 0.023(2) C4 0.041(2) 0.0228(19) 0.035(2) -0.0140(17) 0.0083(17) -0.0034(16) C12 0.031(2) 0.038(2) 0.0262(19) 0.0018(17) -0.0010(16) 0.0100(16) C11 0.036(2) 0.035(2) 0.0221(19) 0.0042(16) -0.0039(16) 0.0086(17) O1W 0.0539(17) 0.0277(14) 0.0541(17) -0.0062(13) -0.0284(14) 0.0022(12) C15 0.0196(16) 0.0262(18) 0.0199(16) -0.0146(14) -0.0032(13) 0.0048(13) _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 1.940(2) . ? Co1 O3 1.956(2) 2_656 ? Co1 N1 2.003(3) . ? Co1 N3 2.004(3) . ? O2 C16 1.233(4) . ? O3 C17 1.280(4) . ? O3 Co1 1.956(2) 2_656 ? O1 C16 1.273(3) . ? O4 C17 1.219(4) . ? N3 C7 1.310(4) . ? N3 C8 1.368(4) . ? C17 C13 1.505(4) . ? N1 C1 1.314(4) . ? N1 C2 1.369(4) . ? C13 C15 1.380(4) . ? C13 C14 1.394(4) . ? C14 C15 1.380(4) 2_756 ? C14 C16 1.489(4) . ? N4 C7 1.337(4) . ? N4 C9 1.369(4) . ? N4 C10 1.423(4) . ? C10 C11 1.363(5) . ? C10 C12 1.372(5) . ? C1 N2 1.333(4) . ? C1 H1 0.9300 . ? N2 C3 1.367(4) . ? N2 C4 1.431(4) . ? C6 C4 1.356(5) . ? C6 C5 1.380(5) 2_745 ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C3 C2 1.345(5) . ? C3 H3 0.9300 . ? C9 C8 1.331(5) . ? C9 H9 0.9300 . ? C5 C4 1.356(5) . ? C5 C6 1.380(5) 2_745 ? C5 H5 0.9300 . ? C2 H2 0.9300 . ? C8 H8 0.9300 . ? C12 C11 1.382(5) 2_764 ? C12 H12 0.9300 . ? C11 C12 1.382(5) 2_764 ? C11 H11 0.9300 . ? O1W H1A 0.8517 . ? O1W H1B 0.8543 . ? C15 C14 1.380(4) 2_756 ? C15 H15 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 O1 Co1 O3 105.25(9) . 2_656 ? O1 Co1 N1 112.19(11) . . ? O3 Co1 N1 113.89(11) 2_656 . ? O1 Co1 N3 112.77(11) . . ? O3 Co1 N3 98.64(11) 2_656 . ? N1 Co1 N3 113.14(11) . . ? C17 O3 Co1 123.4(2) . 2_656 ? C16 O1 Co1 111.14(19) . . ? C7 N3 C8 105.4(3) . . ? C7 N3 Co1 130.9(2) . . ? C8 N3 Co1 123.6(2) . . ? O4 C17 O3 125.6(3) . . ? O4 C17 C13 120.0(3) . . ? O3 C17 C13 114.2(3) . . ? C1 N1 C2 106.1(3) . . ? C1 N1 Co1 128.5(2) . . ? C2 N1 Co1 124.5(2) . . ? C15 C13 C14 118.8(3) . . ? C15 C13 C17 116.7(3) . . ? C14 C13 C17 124.5(3) . . ? C15 C14 C13 118.6(3) 2_756 . ? C15 C14 C16 118.7(3) 2_756 . ? C13 C14 C16 122.7(3) . . ? O2 C16 O1 123.2(3) . . ? O2 C16 C14 120.9(3) . . ? O1 C16 C14 115.8(3) . . ? C7 N4 C9 106.3(3) . . ? C7 N4 C10 127.1(3) . . ? C9 N4 C10 126.5(3) . . ? C11 C10 C12 119.9(3) . . ? C11 C10 N4 120.6(3) . . ? C12 C10 N4 119.5(3) . . ? N1 C1 N2 110.8(3) . . ? N1 C1 H1 124.6 . . ? N2 C1 H1 124.6 . . ? C1 N2 C3 107.6(3) . . ? C1 N2 C4 126.7(3) . . ? C3 N2 C4 125.6(3) . . ? C4 C6 C5 118.9(4) . 2_745 ? C4 C6 H6 120.6 . . ? C5 C6 H6 120.6 2_745 . ? N3 C7 N4 111.7(3) . . ? N3 C7 H7 124.2 . . ? N4 C7 H7 124.2 . . ? C2 C3 N2 106.1(3) . . ? C2 C3 H3 126.9 . . ? N2 C3 H3 126.9 . . ? C8 C9 N4 106.8(3) . . ? C8 C9 H9 126.6 . . ? N4 C9 H9 126.6 . . ? C4 C5 C6 120.5(4) . 2_745 ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 2_745 . ? C3 C2 N1 109.4(3) . . ? C3 C2 H2 125.3 . . ? N1 C2 H2 125.3 . . ? C9 C8 N3 109.8(3) . . ? C9 C8 H8 125.1 . . ? N3 C8 H8 125.1 . . ? C6 C4 C5 120.6(3) . . ? C6 C4 N2 119.8(3) . . ? C5 C4 N2 119.6(3) . . ? C10 C12 C11 119.3(3) . 2_764 ? C10 C12 H12 120.3 . . ? C11 C12 H12 120.3 2_764 . ? C10 C11 C12 120.8(3) . 2_764 ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 2_764 . ? H1A O1W H1B 98.4 . . ? C14 C15 C13 122.6(3) 2_756 . ? C14 C15 H15 118.7 2_756 . ? C13 C15 H15 118.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Co1 O1 C16 -170.7(2) 2_656 . . . ? N1 Co1 O1 C16 64.9(2) . . . . ? N3 Co1 O1 C16 -64.2(2) . . . . ? O1 Co1 N3 C7 85.5(3) . . . . ? O3 Co1 N3 C7 -163.9(3) 2_656 . . . ? N1 Co1 N3 C7 -43.2(3) . . . . ? O1 Co1 N3 C8 -91.3(3) . . . . ? O3 Co1 N3 C8 19.4(3) 2_656 . . . ? N1 Co1 N3 C8 140.1(3) . . . . ? Co1 O3 C17 O4 5.0(4) 2_656 . . . ? Co1 O3 C17 C13 -179.92(18) 2_656 . . . ? O1 Co1 N1 C1 -86.7(3) . . . . ? O3 Co1 N1 C1 153.9(3) 2_656 . . . ? N3 Co1 N1 C1 42.3(3) . . . . ? O1 Co1 N1 C2 80.6(3) . . . . ? O3 Co1 N1 C2 -38.8(3) 2_656 . . . ? N3 Co1 N1 C2 -150.4(3) . . . . ? O4 C17 C13 C15 102.9(3) . . . . ? O3 C17 C13 C15 -72.4(4) . . . . ? O4 C17 C13 C14 -74.3(4) . . . . ? O3 C17 C13 C14 110.3(3) . . . . ? C15 C13 C14 C15 0.0(5) . . . 2_756 ? C17 C13 C14 C15 177.2(3) . . . 2_756 ? C15 C13 C14 C16 177.6(3) . . . . ? C17 C13 C14 C16 -5.2(5) . . . . ? Co1 O1 C16 O2 -1.3(4) . . . . ? Co1 O1 C16 C14 -179.54(19) . . . . ? C15 C14 C16 O2 -15.0(4) 2_756 . . . ? C13 C14 C16 O2 167.4(3) . . . . ? C15 C14 C16 O1 163.2(3) 2_756 . . . ? C13 C14 C16 O1 -14.4(4) . . . . ? C7 N4 C10 C11 -16.0(6) . . . . ? C9 N4 C10 C11 165.8(4) . . . . ? C7 N4 C10 C12 163.4(4) . . . . ? C9 N4 C10 C12 -14.8(6) . . . . ? C2 N1 C1 N2 0.1(4) . . . . ? Co1 N1 C1 N2 169.2(2) . . . . ? N1 C1 N2 C3 -0.7(5) . . . . ? N1 C1 N2 C4 -177.4(3) . . . . ? C8 N3 C7 N4 -0.2(4) . . . . ? Co1 N3 C7 N4 -177.4(2) . . . . ? C9 N4 C7 N3 0.1(4) . . . . ? C10 N4 C7 N3 -178.3(3) . . . . ? C1 N2 C3 C2 1.1(5) . . . . ? C4 N2 C3 C2 177.8(4) . . . . ? C7 N4 C9 C8 0.0(5) . . . . ? C10 N4 C9 C8 178.5(4) . . . . ? N2 C3 C2 N1 -1.1(6) . . . . ? C1 N1 C2 C3 0.7(5) . . . . ? Co1 N1 C2 C3 -169.0(3) . . . . ? N4 C9 C8 N3 -0.1(6) . . . . ? C7 N3 C8 C9 0.2(5) . . . . ? Co1 N3 C8 C9 177.7(3) . . . . ? C5 C6 C4 C5 1.3(8) 2_745 . . . ? C5 C6 C4 N2 -179.6(4) 2_745 . . . ? C6 C5 C4 C6 -1.4(8) 2_745 . . . ? C6 C5 C4 N2 179.6(4) 2_745 . . . ? C1 N2 C4 C6 142.4(4) . . . . ? C3 N2 C4 C6 -33.7(6) . . . . ? C1 N2 C4 C5 -38.6(6) . . . . ? C3 N2 C4 C5 145.3(5) . . . . ? C11 C10 C12 C11 -0.6(7) . . . 2_764 ? N4 C10 C12 C11 -179.9(3) . . . 2_764 ? C12 C10 C11 C12 0.6(7) . . . 2_764 ? N4 C10 C11 C12 179.9(3) . . . 2_764 ? C14 C13 C15 C14 0.0(5) . . . 2_756 ? C17 C13 C15 C14 -177.4(3) . . . 2_756 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.295 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.075