# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C13 H9 Co N O5' _chemical_formula_sum 'C13 H9 Co N O5' _chemical_formula_weight 318.14 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 Orthorhombic _symmetry_space_group_name_H-M Imma _symmetry_space_group_name_Hall '-I 2b 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z' '-x, y+1/2, -z' 'x, -y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1, z+1/2' '-x+1/2, y+1, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x, y-1/2, -z' 'x, -y-1/2, z' '-x, y, z' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y, -z+1/2' 'x+1/2, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 19.392(12) _cell_length_b 7.228(5) _cell_length_c 9.387(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1315.9(14) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 755 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 26.58 _exptl_crystal_description needle _exptl_crystal_colour pink _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 1.321 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7516 _exptl_absorpt_correction_T_max 0.8315 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 3229 _diffrn_reflns_av_R_equivalents 0.0606 _diffrn_reflns_av_sigmaI/netI 0.0509 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 26.58 _reflns_number_total 755 _reflns_number_gt 651 _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 SHELXP-97 _computing_publication_material 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^)+(0.0730P)^2^+9.2976P] 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 755 _refine_ls_number_parameters 59 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1620 _refine_ls_wR_factor_gt 0.1593 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _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 0.5000 0.0000 0.5000 0.0177(4) Uani 1 4 d S . . O1 O 0.5000 0.2500 0.3859(6) 0.0273(14) Uani 1 4 d S . . O2 O 0.42160(16) 0.0954(4) 0.6325(3) 0.0327(8) Uani 1 1 d . . . N1 N 0.5000 0.2500 0.2423(7) 0.0246(15) Uani 1 4 d S . . C6 C 0.3937(3) 0.2500 0.6497(6) 0.0249(13) Uani 1 2 d S . . C7 C 0.3185(3) 0.2500 0.7025(6) 0.0262(13) Uani 1 2 d S . . C3 C 0.4385(4) 0.2500 0.1725(7) 0.0417(18) Uani 1 2 d S . . H3 H 0.3973 0.2500 0.2232 0.080 Uiso 1 2 calc S . . C8 C 0.2845(3) 0.0894(7) 0.7253(9) 0.062(2) Uani 1 1 d . . . H8 H 0.3067 -0.0225 0.7084 0.080 Uiso 1 1 calc . . . C4 C 0.4382(5) 0.2500 0.0249(8) 0.053(2) Uani 1 2 d S . . H4 H 0.3965 0.2500 -0.0243 0.080 Uiso 1 2 calc S . . C5 C 0.5000 0.2500 -0.0493(12) 0.054(3) Uani 1 4 d S . . H5 H 0.5000 0.2500 -0.1483 0.080 Uiso 1 4 calc S . . 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 0.0150(6) 0.0191(6) 0.0191(6) 0.0002(4) 0.000 0.000 O1 0.043(4) 0.022(3) 0.017(3) 0.000 0.000 0.000 O2 0.0260(16) 0.0292(18) 0.0430(18) 0.0025(14) 0.0139(13) 0.0069(14) N1 0.030(4) 0.024(4) 0.020(3) 0.000 0.000 0.000 C6 0.014(3) 0.036(3) 0.026(3) 0.000 0.005(2) 0.000 C7 0.023(3) 0.028(3) 0.028(3) 0.000 0.012(2) 0.000 C3 0.039(4) 0.056(5) 0.030(3) 0.000 -0.006(3) 0.000 C8 0.034(3) 0.028(3) 0.126(6) -0.008(3) 0.035(3) 0.006(2) C4 0.056(5) 0.077(6) 0.027(4) 0.000 -0.011(3) 0.000 C5 0.060(8) 0.075(9) 0.025(5) 0.000 0.000 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O2 2.082(3) 12_655 ? Co1 O2 2.082(3) 4_556 ? Co1 O2 2.082(3) 9_656 ? Co1 O2 2.082(3) . ? Co1 O1 2.101(3) . ? Co1 O1 2.101(3) 9_656 ? O1 N1 1.348(9) . ? O1 Co1 2.101(3) 2_655 ? O2 C6 1.253(4) . ? N1 C3 1.361(8) . ? N1 C3 1.361(8) 2_655 ? C6 O2 1.253(4) 11_565 ? C6 C7 1.539(8) . ? C7 C8 1.352(6) . ? C7 C8 1.352(6) 11_565 ? C3 C4 1.385(10) . ? C8 C8 1.416(10) 7_546 ? C4 C5 1.387(11) . ? C5 C4 1.387(11) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Co1 O2 180.00(11) 12_655 4_556 ? O2 Co1 O2 86.16(19) 12_655 9_656 ? O2 Co1 O2 93.84(19) 4_556 9_656 ? O2 Co1 O2 93.84(19) 12_655 . ? O2 Co1 O2 86.16(19) 4_556 . ? O2 Co1 O2 180.00(11) 9_656 . ? O2 Co1 O1 91.13(13) 12_655 . ? O2 Co1 O1 88.87(13) 4_556 . ? O2 Co1 O1 88.87(13) 9_656 . ? O2 Co1 O1 91.13(13) . . ? O2 Co1 O1 88.87(13) 12_655 9_656 ? O2 Co1 O1 91.13(13) 4_556 9_656 ? O2 Co1 O1 91.13(13) 9_656 9_656 ? O2 Co1 O1 88.87(13) . 9_656 ? O1 Co1 O1 180.0 . 9_656 ? N1 O1 Co1 120.65(13) . 2_655 ? N1 O1 Co1 120.65(13) . . ? Co1 O1 Co1 118.7(3) 2_655 . ? C6 O2 Co1 133.5(3) . . ? O1 N1 C3 118.8(4) . . ? O1 N1 C3 118.8(4) . 2_655 ? C3 N1 C3 122.4(8) . 2_655 ? O2 C6 O2 126.4(5) 11_565 . ? O2 C6 C7 116.8(3) 11_565 . ? O2 C6 C7 116.8(3) . . ? C8 C7 C8 118.3(6) . 11_565 ? C8 C7 C6 120.9(3) . . ? C8 C7 C6 120.9(3) 11_565 . ? N1 C3 C4 119.1(7) . . ? C7 C8 C8 120.9(3) . 7_546 ? C3 C4 C5 119.9(8) . . ? C4 C5 C4 119.7(10) 2_655 . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.58 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.513 _refine_diff_density_min -0.679 _refine_diff_density_rms 0.125 _database_code_depnum_ccdc_archive 'CCDC 958327' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C14 H11 Co N O5' _chemical_formula_sum 'C14 H11 Co N O5' _chemical_formula_weight 332.17 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 Orthorhombic _symmetry_space_group_name_H-M Pnma _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 7.1654(3) _cell_length_b 18.5414(8) _cell_length_c 10.8922(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1447.10(11) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1326 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 25.05 _exptl_crystal_description needle _exptl_crystal_colour pink _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 1.205 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8362 _exptl_absorpt_correction_T_max 0.8761 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 6850 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1326 _reflns_number_gt 1215 _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 SHELXP-97 _computing_publication_material 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^)+(0.0302P)^2^+1.2345P] 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 1326 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0276 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0656 _refine_ls_wR_factor_gt 0.0647 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 0.22535(5) 0.7500 0.24301(3) 0.01030(13) Uani 1 2 d S . . O1 O 0.31892(19) 0.66876(7) 0.12741(12) 0.0204(3) Uani 1 1 d . . . O2 O -0.0296(2) 0.7500 0.15224(16) 0.0174(4) Uani 1 2 d S . . O3 O 0.63157(19) 0.66918(7) 0.14328(12) 0.0214(3) Uani 1 1 d . . . N1 N -0.0385(3) 0.7500 0.0297(2) 0.0183(5) Uani 1 2 d S . . C1 C 0.4784(3) 0.64181(10) 0.11379(17) 0.0166(4) Uani 1 1 d . . . C2 C 0.4885(3) 0.56812(11) 0.05468(19) 0.0197(4) Uani 1 1 d . . . C3 C 0.6473(3) 0.52638(12) 0.0679(2) 0.0337(6) Uani 1 1 d . . . H3 H 0.7472 0.5437 0.1139 0.080 Uiso 1 1 calc . . . C4 C 0.3413(3) 0.54103(12) -0.0132(2) 0.0339(6) Uani 1 1 d . . . H4 H 0.2333 0.5683 -0.0222 0.080 Uiso 1 1 calc . . . C5 C -0.0432(3) 0.68691(12) -0.03028(19) 0.0261(5) Uani 1 1 d . . . H5 H -0.0432 0.6438 0.0132 0.080 Uiso 1 1 calc . . . C6 C -0.0480(3) 0.68630(14) -0.1566(2) 0.0336(6) Uani 1 1 d . . . H6 H -0.0506 0.6425 -0.1981 0.080 Uiso 1 1 calc . . . C7 C -0.0490(5) 0.7500 -0.2228(3) 0.0348(8) Uani 1 2 d S . . C8 C -0.0513(6) 0.7500 -0.3607(3) 0.0536(12) Uani 1 2 d S . . H8A H -0.0516 0.7012 -0.3900 0.080 Uiso 0.50 1 calc PR . . H8B H 0.0574 0.7745 -0.3908 0.080 Uiso 0.50 1 calc PR . . H8C H -0.1614 0.7743 -0.3892 0.080 Uiso 0.50 1 calc PR . . 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 0.0113(2) 0.00905(19) 0.01058(19) 0.000 0.00077(13) 0.000 O1 0.0191(7) 0.0177(7) 0.0244(7) -0.0089(6) 0.0004(6) 0.0028(6) O2 0.0142(10) 0.0300(11) 0.0080(9) 0.000 -0.0004(7) 0.000 O3 0.0188(7) 0.0191(7) 0.0264(7) -0.0112(6) -0.0002(6) -0.0028(6) N1 0.0146(12) 0.0278(13) 0.0125(11) 0.000 0.0002(9) 0.000 C1 0.0202(10) 0.0144(10) 0.0150(9) -0.0028(8) 0.0006(8) -0.0004(8) C2 0.0172(10) 0.0170(10) 0.0249(10) -0.0084(8) 0.0002(8) -0.0006(8) C3 0.0219(11) 0.0270(11) 0.0523(14) -0.0191(11) -0.0131(11) 0.0030(10) C4 0.0202(11) 0.0266(12) 0.0549(15) -0.0186(11) -0.0099(11) 0.0070(9) C5 0.0266(12) 0.0295(12) 0.0221(11) -0.0054(9) 0.0007(9) 0.0046(9) C6 0.0328(13) 0.0457(15) 0.0223(11) -0.0120(11) -0.0002(10) 0.0030(11) C7 0.0231(17) 0.065(2) 0.0161(15) 0.000 -0.0012(13) 0.000 C8 0.043(2) 0.102(4) 0.0154(17) 0.000 0.0000(16) 0.000 _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 2.0569(13) 4_465 ? Co1 O3 2.0569(13) 6_556 ? Co1 O1 2.0745(13) 7_575 ? Co1 O1 2.0745(13) . ? Co1 O2 2.0775(18) . ? Co1 O2 2.0938(18) 6_656 ? O1 C1 1.256(2) . ? O2 N1 1.336(3) . ? O2 Co1 2.0938(18) 6_556 ? O3 C1 1.251(2) . ? O3 Co1 2.0569(13) 6_656 ? N1 C5 1.340(2) 7_575 ? N1 C5 1.340(2) . ? C1 C2 1.512(3) . ? C2 C4 1.382(3) . ? C2 C3 1.384(3) . ? C3 C4 1.387(3) 5_665 ? C4 C3 1.387(3) 5_665 ? C5 C6 1.377(3) . ? C6 C7 1.383(3) . ? C7 C6 1.383(3) 7_575 ? C7 C8 1.502(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 O3 Co1 O3 93.52(8) 4_465 6_556 ? O3 Co1 O1 86.68(5) 4_465 7_575 ? O3 Co1 O1 179.63(6) 6_556 7_575 ? O3 Co1 O1 179.63(6) 4_465 . ? O3 Co1 O1 86.68(5) 6_556 . ? O1 Co1 O1 93.11(8) 7_575 . ? O3 Co1 O2 89.96(5) 4_465 . ? O3 Co1 O2 89.96(5) 6_556 . ? O1 Co1 O2 89.73(5) 7_575 . ? O1 Co1 O2 89.73(5) . . ? O3 Co1 O2 86.89(5) 4_465 6_656 ? O3 Co1 O2 86.89(5) 6_556 6_656 ? O1 Co1 O2 93.43(5) 7_575 6_656 ? O1 Co1 O2 93.43(5) . 6_656 ? O2 Co1 O2 175.40(5) . 6_656 ? C1 O1 Co1 130.90(12) . . ? N1 O2 Co1 121.16(15) . . ? N1 O2 Co1 120.28(15) . 6_556 ? Co1 O2 Co1 118.56(8) . 6_556 ? C1 O3 Co1 137.45(12) . 6_656 ? O2 N1 C5 119.23(12) . 7_575 ? O2 N1 C5 119.23(12) . . ? C5 N1 C5 121.5(2) 7_575 . ? O3 C1 O1 127.32(17) . . ? O3 C1 C2 115.71(16) . . ? O1 C1 C2 116.97(16) . . ? C4 C2 C3 118.69(19) . . ? C4 C2 C1 121.30(18) . . ? C3 C2 C1 120.01(18) . . ? C2 C3 C4 120.49(19) . 5_665 ? C2 C4 C3 120.8(2) . 5_665 ? N1 C5 C6 119.7(2) . . ? C5 C6 C7 120.9(2) . . ? C6 C7 C6 117.2(3) 7_575 . ? C6 C7 C8 121.38(14) 7_575 . ? C6 C7 C8 121.38(14) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.390 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 958326'