data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18.40 Co2 N2 O10.20' _chemical_formula_weight 567.83 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 9.8886(19) _cell_length_b 11.102(2) _cell_length_c 11.914(2) _cell_angle_alpha 64.317(3) _cell_angle_beta 78.159(3) _cell_angle_gamma 68.485(3) _cell_volume 1094.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 759 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 22.83 _exptl_crystal_description block _exptl_crystal_colour violet _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.722 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 1.577 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7300 _exptl_absorpt_correction_T_max 0.8896 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _diffrn_ambient_temperature 173(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 SMART APEX CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5863 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.1023 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3936 _reflns_number_gt 2693 _reflns_threshold_expression >2\s(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_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^)+(0.0879P)^2^+1.7873P] 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 3936 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1049 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.1890 _refine_ls_wR_factor_gt 0.1661 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.004 _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 0.17536(10) 0.94416(10) 0.48263(9) 0.0160(3) Uani 1 1 d . . . Co2 Co -0.06762(11) 1.00893(10) 0.27518(9) 0.0186(3) Uani 1 1 d . . . O1 O 0.1709(5) 0.7827(5) 0.4434(5) 0.0201(12) Uani 1 1 d . . . O2 O 0.0885(6) 0.6491(5) 0.6263(5) 0.0257(13) Uani 1 1 d . . . O3 O 0.4830(6) 0.4650(5) 0.2425(5) 0.0273(13) Uani 1 1 d . . . O4 O 0.6736(5) 0.2089(5) 0.3799(5) 0.0238(12) Uani 1 1 d . . . O5 O 0.7528(6) 0.1638(5) 0.2062(5) 0.0251(12) Uani 1 1 d . . . O6 O 0.2133(6) 0.1098(5) 0.4981(5) 0.0261(13) Uani 1 1 d . . . O7 O 0.1055(5) 0.1725(5) 0.6567(5) 0.0201(12) Uani 1 1 d . . . O8 O -0.0020(5) 1.0757(5) 0.3751(4) 0.0175(11) Uani 1 1 d . . . H8 H -0.0172 1.1648 0.3351 0.021 Uiso 1 1 d R . . N1 N 0.0745(7) 1.0061(6) 0.1276(6) 0.0204(14) Uani 1 1 d . . . N2 N 0.6572(6) 1.0348(6) -0.3370(6) 0.0199(14) Uani 1 1 d . . . C1 C 0.1540(8) 0.6679(8) 0.5215(7) 0.0194(16) Uani 1 1 d . . . C2 C 0.2165(7) 0.5466(7) 0.4803(7) 0.0159(15) Uani 1 1 d . . . C3 C 0.3228(8) 0.5533(7) 0.3823(7) 0.0195(16) Uani 1 1 d . . . H3 H 0.3564 0.6329 0.3442 0.023 Uiso 1 1 calc R . . C4 C 0.3800(8) 0.4444(7) 0.3399(7) 0.0182(16) Uani 1 1 d . . . C5 C 0.3309(8) 0.3281(8) 0.3946(7) 0.0232(17) Uani 1 1 d . . . H5 H 0.3678 0.2550 0.3645 0.028 Uiso 1 1 calc R . . C6 C 0.2273(7) 0.3195(8) 0.4938(7) 0.0169(16) Uani 1 1 d . . . C7 C 0.1709(7) 0.4261(7) 0.5388(7) 0.0183(16) Uani 1 1 d . . . H7 H 0.1024 0.4176 0.6083 0.022 Uiso 1 1 calc R . . C8 C 0.5494(8) 0.3618(8) 0.1901(7) 0.0233(18) Uani 1 1 d . . . H8A H 0.5926 0.4061 0.1060 0.028 Uiso 1 1 calc R . . H8B H 0.4734 0.3292 0.1805 0.028 Uiso 1 1 calc R . . C9 C 0.6682(8) 0.2339(8) 0.2689(7) 0.0220(18) Uani 1 1 d . . . C10 C 0.1774(7) 0.1917(7) 0.5538(7) 0.0175(16) Uani 1 1 d . . . C11 C 0.1794(9) 0.8893(8) 0.1276(7) 0.0278(19) Uani 1 1 d . . . H11 H 0.1745 0.8019 0.1916 0.033 Uiso 1 1 calc R . . C12 C 0.2950(9) 0.8875(8) 0.0400(8) 0.031(2) Uani 1 1 d . . . H12 H 0.3679 0.8010 0.0457 0.037 Uiso 1 1 calc R . . C13 C 0.3041(8) 1.0134(8) -0.0566(7) 0.0219(17) Uani 1 1 d . . . C14 C 0.1927(10) 1.1345(9) -0.0594(9) 0.047(3) Uani 1 1 d . . . H14 H 0.1922 1.2231 -0.1242 0.056 Uiso 1 1 calc R . . C15 C 0.0809(11) 1.1249(9) 0.0342(9) 0.045(3) Uani 1 1 d . . . H15 H 0.0048 1.2091 0.0304 0.054 Uiso 1 1 calc R . . C16 C 0.4272(8) 1.0193(8) -0.1519(7) 0.0188(16) Uani 1 1 d . . . C17 C 0.5507(9) 0.9026(9) -0.1444(8) 0.031(2) Uani 1 1 d . . . H17 H 0.5591 0.8151 -0.0755 0.037 Uiso 1 1 calc R . . C18 C 0.6604(9) 0.9150(8) -0.2380(7) 0.0290(19) Uani 1 1 d . . . H18 H 0.7424 0.8340 -0.2313 0.035 Uiso 1 1 calc R . . C19 C 0.5405(8) 1.1469(8) -0.3428(7) 0.0218(17) Uani 1 1 d . . . H19 H 0.5367 1.2334 -0.4118 0.026 Uiso 1 1 calc R . . C20 C 0.4248(8) 1.1446(8) -0.2545(7) 0.0234(17) Uani 1 1 d . . . H20 H 0.3445 1.2276 -0.2639 0.028 Uiso 1 1 calc R . . O1W O 0.2751(10) 0.4351(8) 0.8091(8) 0.082(3) Uani 1 1 d . . . H1A H 0.2040 0.5047 0.7675 0.098 Uiso 1 1 d R . . H1B H 0.3506 0.4644 0.7911 0.098 Uiso 1 1 d R . . O2W O -0.0644(15) 0.4604(15) 0.8040(14) 0.059(4) Uani 0.50 1 d P . . O3W O 0.2453(16) 0.4249(14) 1.0468(12) 0.053(4) Uani 0.50 1 d P . . O4W O 0.052(5) 0.473(4) 0.867(4) 0.077(12) Uiso 0.20 1 d P . . 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 0.0171(5) 0.0146(5) 0.0202(6) -0.0111(5) 0.0087(4) -0.0093(4) Co2 0.0212(6) 0.0178(6) 0.0218(6) -0.0128(5) 0.0108(4) -0.0118(4) O1 0.026(3) 0.015(3) 0.023(3) -0.011(2) 0.004(2) -0.009(2) O2 0.033(3) 0.019(3) 0.027(3) -0.013(2) 0.012(3) -0.013(2) O3 0.028(3) 0.022(3) 0.036(3) -0.017(3) 0.017(3) -0.015(2) O4 0.019(3) 0.028(3) 0.025(3) -0.014(3) 0.006(2) -0.007(2) O5 0.028(3) 0.025(3) 0.024(3) -0.014(2) 0.003(2) -0.007(2) O6 0.029(3) 0.023(3) 0.037(3) -0.020(3) 0.012(3) -0.018(3) O7 0.023(3) 0.015(3) 0.023(3) -0.008(2) 0.007(2) -0.011(2) O8 0.022(3) 0.011(3) 0.019(3) -0.006(2) 0.006(2) -0.007(2) N1 0.025(3) 0.018(3) 0.018(3) -0.007(3) 0.008(3) -0.012(3) N2 0.020(3) 0.020(3) 0.023(4) -0.011(3) 0.007(3) -0.011(3) C1 0.018(4) 0.022(4) 0.026(4) -0.014(4) 0.003(3) -0.012(3) C2 0.013(4) 0.013(4) 0.026(4) -0.009(3) -0.002(3) -0.007(3) C3 0.020(4) 0.012(4) 0.027(4) -0.009(3) 0.004(3) -0.008(3) C4 0.016(4) 0.017(4) 0.023(4) -0.012(3) 0.003(3) -0.004(3) C5 0.027(4) 0.014(4) 0.032(5) -0.013(4) 0.001(3) -0.007(3) C6 0.013(4) 0.019(4) 0.023(4) -0.013(3) 0.000(3) -0.006(3) C7 0.015(4) 0.017(4) 0.022(4) -0.009(3) 0.004(3) -0.005(3) C8 0.024(4) 0.020(4) 0.028(4) -0.014(4) 0.010(3) -0.009(3) C9 0.024(4) 0.024(4) 0.028(5) -0.016(4) 0.015(3) -0.020(4) C10 0.016(4) 0.014(4) 0.023(4) -0.007(3) -0.002(3) -0.004(3) C11 0.031(5) 0.011(4) 0.025(5) -0.001(3) 0.009(4) -0.003(4) C12 0.027(5) 0.015(4) 0.035(5) -0.009(4) 0.011(4) 0.004(3) C13 0.023(4) 0.027(4) 0.021(4) -0.015(4) 0.008(3) -0.012(3) C14 0.043(6) 0.027(5) 0.049(6) -0.011(5) 0.031(5) -0.009(4) C15 0.052(6) 0.024(5) 0.045(6) -0.017(5) 0.027(5) -0.010(4) C16 0.025(4) 0.023(4) 0.016(4) -0.013(3) 0.008(3) -0.013(3) C17 0.031(5) 0.026(5) 0.037(5) -0.017(4) 0.019(4) -0.015(4) C18 0.040(5) 0.022(4) 0.029(5) -0.012(4) 0.009(4) -0.018(4) C19 0.023(4) 0.022(4) 0.019(4) -0.009(3) 0.003(3) -0.007(3) C20 0.025(4) 0.024(4) 0.019(4) -0.008(4) 0.001(3) -0.007(3) O1W 0.088(7) 0.058(5) 0.098(7) -0.018(5) -0.011(5) -0.036(5) O2W 0.050(9) 0.052(9) 0.065(10) -0.015(8) -0.001(8) -0.016(7) O3W 0.067(10) 0.041(8) 0.032(8) 0.001(6) -0.013(7) -0.012(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 Co1 O1 2.056(5) . ? Co1 O8 2.067(5) . ? Co1 O6 2.094(5) 1_565 ? Co1 O4 2.129(5) 2_666 ? Co1 N2 2.135(6) 2_675 ? Co1 O8 2.149(5) 2_576 ? Co2 O8 1.956(5) . ? Co2 O7 1.967(5) 2_566 ? Co2 O5 1.980(5) 1_465 ? Co2 N1 2.017(6) . ? O1 C1 1.257(8) . ? O2 C1 1.251(9) . ? O3 C4 1.376(8) . ? O3 C8 1.426(8) . ? O4 C9 1.237(9) . ? O4 Co1 2.129(5) 2_666 ? O5 C9 1.277(9) . ? O5 Co2 1.980(5) 1_645 ? O6 C10 1.258(8) . ? O6 Co1 2.094(5) 1_545 ? O7 C10 1.257(8) . ? O7 Co2 1.967(5) 2_566 ? O8 Co1 2.149(5) 2_576 ? O8 H8 0.8600 . ? N1 C15 1.320(10) . ? N1 C11 1.331(9) . ? N2 C18 1.337(10) . ? N2 C19 1.337(9) . ? N2 Co1 2.135(6) 2_675 ? C1 C2 1.509(10) . ? C2 C3 1.397(10) . ? C2 C7 1.408(9) . ? C3 C4 1.396(10) . ? C3 H3 0.9500 . ? C4 C5 1.388(10) . ? C5 C6 1.390(10) . ? C5 H5 0.9500 . ? C6 C7 1.393(10) . ? C6 C10 1.503(9) . ? C7 H7 0.9500 . ? C8 C9 1.533(11) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C11 C12 1.381(10) . ? C11 H11 0.9500 . ? C12 C13 1.394(11) . ? C12 H12 0.9500 . ? C13 C14 1.382(11) . ? C13 C16 1.484(9) . ? C14 C15 1.399(11) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C17 1.401(11) . ? C16 C20 1.394(10) . ? C17 C18 1.385(10) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.386(10) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? O1W H1A 0.8656 . ? O1W H1B 0.8721 . ? O2W O4W 1.57(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O8 89.10(19) . . ? O1 Co1 O6 169.2(2) . 1_565 ? O8 Co1 O6 93.4(2) . 1_565 ? O1 Co1 O4 87.7(2) . 2_666 ? O8 Co1 O4 168.33(18) . 2_666 ? O6 Co1 O4 91.7(2) 1_565 2_666 ? O1 Co1 N2 85.0(2) . 2_675 ? O8 Co1 N2 98.4(2) . 2_675 ? O6 Co1 N2 84.3(2) 1_565 2_675 ? O4 Co1 N2 92.5(2) 2_666 2_675 ? O1 Co1 O8 94.05(19) . 2_576 ? O8 Co1 O8 80.0(2) . 2_576 ? O6 Co1 O8 96.68(19) 1_565 2_576 ? O4 Co1 O8 89.05(19) 2_666 2_576 ? N2 Co1 O8 178.1(2) 2_675 2_576 ? O8 Co2 O7 123.3(2) . 2_566 ? O8 Co2 O5 102.7(2) . 1_465 ? O7 Co2 O5 109.5(2) 2_566 1_465 ? O8 Co2 N1 109.3(2) . . ? O7 Co2 N1 105.1(2) 2_566 . ? O5 Co2 N1 105.9(2) 1_465 . ? C1 O1 Co1 126.3(5) . . ? C4 O3 C8 120.2(5) . . ? C9 O4 Co1 132.7(5) . 2_666 ? C9 O5 Co2 121.6(5) . 1_645 ? C10 O6 Co1 146.1(5) . 1_545 ? C10 O7 Co2 111.0(4) . 2_566 ? Co2 O8 Co1 119.1(2) . . ? Co2 O8 Co1 96.31(19) . 2_576 ? Co1 O8 Co1 100.0(2) . 2_576 ? Co2 O8 H8 108.0 . . ? Co1 O8 H8 122.7 . . ? Co1 O8 H8 105.4 2_576 . ? C15 N1 C11 116.6(7) . . ? C15 N1 Co2 120.4(5) . . ? C11 N1 Co2 122.2(5) . . ? C18 N2 C19 116.5(7) . . ? C18 N2 Co1 124.1(5) . 2_675 ? C19 N2 Co1 119.3(5) . 2_675 ? O2 C1 O1 125.4(7) . . ? O2 C1 C2 119.2(6) . . ? O1 C1 C2 115.4(6) . . ? C3 C2 C7 119.2(6) . . ? C3 C2 C1 119.3(6) . . ? C7 C2 C1 121.6(6) . . ? C4 C3 C2 120.6(6) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? O3 C4 C5 125.3(6) . . ? O3 C4 C3 114.6(6) . . ? C5 C4 C3 120.1(7) . . ? C6 C5 C4 119.5(7) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C7 121.2(6) . . ? C5 C6 C10 118.9(6) . . ? C7 C6 C10 119.9(6) . . ? C6 C7 C2 119.4(6) . . ? C6 C7 H7 120.3 . . ? C2 C7 H7 120.3 . . ? O3 C8 C9 113.5(6) . . ? O3 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? O3 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? O4 C9 O5 127.6(8) . . ? O4 C9 C8 120.2(7) . . ? O5 C9 C8 112.2(7) . . ? O7 C10 O6 124.6(6) . . ? O7 C10 C6 118.1(6) . . ? O6 C10 C6 117.3(6) . . ? N1 C11 C12 123.9(7) . . ? N1 C11 H11 118.1 . . ? C12 C11 H11 118.1 . . ? C11 C12 C13 119.6(7) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 116.7(7) . . ? C14 C13 C16 120.9(7) . . ? C12 C13 C16 122.3(7) . . ? C13 C14 C15 119.2(8) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? N1 C15 C14 124.0(8) . . ? N1 C15 H15 118.0 . . ? C14 C15 H15 118.0 . . ? C17 C16 C20 116.5(7) . . ? C17 C16 C13 122.9(7) . . ? C20 C16 C13 120.6(7) . . ? C18 C17 C16 119.8(8) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? N2 C18 C17 123.6(8) . . ? N2 C18 H18 118.2 . . ? C17 C18 H18 118.2 . . ? N2 C19 C20 124.1(7) . . ? N2 C19 H19 117.9 . . ? C20 C19 H19 117.9 . . ? C19 C20 C16 119.4(7) . . ? C19 C20 H20 120.3 . . ? C16 C20 H20 120.3 . . ? H1A O1W H1B 107.4 . . ? 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 O8 H8 O2 0.86 2.14 2.847(7) 139 2_576 O1W H1A O2 0.87 1.95 2.782(10) 160 . O1W H1B O3 0.87 1.97 2.843(10) 177 2_666 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.040 _refine_diff_density_min -0.740 _refine_diff_density_rms 0.143