# 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_l #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H4 Mn O4' _chemical_formula_weight 219.05 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 4.664(2) _cell_length_b 13.625(6) _cell_length_c 6.339(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.82(3) _cell_angle_gamma 90.00 _cell_volume 362.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description strip _exptl_crystal_colour pink _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.006 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 218 _exptl_absorpt_coefficient_mu 1.790 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.630 _exptl_absorpt_correction_T_max 0.699 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2341 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 24.99 _reflns_number_total 642 _reflns_number_gt 627 _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^)+(0.0694P)^2^+0.5648P] 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 geom _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.044(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 642 _refine_ls_number_parameters 63 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1199 _refine_ls_wR_factor_gt 0.1193 _refine_ls_goodness_of_fit_ref 1.218 _refine_ls_restrained_S_all 1.218 _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 Mn1 Mn 0.0000 0.44717(5) 0.7500 0.0146(4) Uani 1 2 d S . . O1 O 0.1976(6) 0.42976(17) 0.4867(4) 0.0159(6) Uani 1 1 d . . . O2 O 0.6362(6) 0.34852(18) 0.5431(5) 0.0228(7) Uani 1 1 d . . . C1 C 0.3412(8) 0.3542(2) 0.4611(6) 0.0160(8) Uani 1 1 d . . . C2 C 0.1561(8) 0.2648(3) 0.3407(7) 0.0184(8) Uani 1 1 d . . . C3 C 0.3050(9) 0.1757(3) 0.4243(8) 0.0289(10) Uani 1 1 d . . . H3A H 0.5127 0.1753 0.5418 0.034(12) Uiso 1 1 d R . . C4 C 0.1526(11) 0.0876(3) 0.3390(9) 0.0401(12) Uani 1 1 d . . . H4A H 0.2554 0.0287 0.4006 0.038(13) 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 Mn1 0.0106(5) 0.0212(5) 0.0107(5) 0.000 0.0034(4) 0.000 O1 0.0152(13) 0.0207(12) 0.0124(13) 0.0006(9) 0.0066(11) 0.0023(9) O2 0.0125(13) 0.0277(14) 0.0247(16) -0.0068(11) 0.0049(12) -0.0014(10) C1 0.0143(17) 0.0216(17) 0.0098(18) 0.0018(13) 0.0031(14) 0.0007(12) C2 0.0128(17) 0.0246(18) 0.0171(18) -0.0001(14) 0.0059(15) 0.0001(14) C3 0.0166(19) 0.028(2) 0.031(2) 0.0008(16) 0.0005(17) 0.0034(15) C4 0.028(2) 0.023(2) 0.056(3) 0.005(2) 0.005(2) 0.0055(18) _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 Mn1 O2 2.114(3) 1_455 ? Mn1 O2 2.114(3) 2_656 ? Mn1 O1 2.170(3) 4_566 ? Mn1 O1 2.170(3) 3_566 ? Mn1 O1 2.243(3) . ? Mn1 O1 2.243(3) 2_556 ? Mn1 Mn1 3.4812(11) 3_567 ? Mn1 Mn1 3.4812(11) 3_566 ? O1 C1 1.276(4) . ? O1 Mn1 2.170(3) 3_566 ? O2 C1 1.243(4) . ? O2 Mn1 2.114(3) 1_655 ? C1 C2 1.496(5) . ? C2 C3 1.384(5) . ? C2 C2 1.408(7) 2 ? C3 C4 1.379(6) . ? C3 H3A 0.9300 . ? C4 C4 1.378(9) 2 ? C4 H4A 0.9301 . ? 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 Mn1 O2 101.03(15) 1_455 2_656 ? O2 Mn1 O1 154.82(10) 1_455 4_566 ? O2 Mn1 O1 94.47(10) 2_656 4_566 ? O2 Mn1 O1 94.47(10) 1_455 3_566 ? O2 Mn1 O1 154.82(10) 2_656 3_566 ? O1 Mn1 O1 78.78(13) 4_566 3_566 ? O2 Mn1 O1 87.13(10) 1_455 . ? O2 Mn1 O1 85.16(10) 2_656 . ? O1 Mn1 O1 114.08(10) 4_566 . ? O1 Mn1 O1 75.85(10) 3_566 . ? O2 Mn1 O1 85.16(10) 1_455 2_556 ? O2 Mn1 O1 87.13(10) 2_656 2_556 ? O1 Mn1 O1 75.85(10) 4_566 2_556 ? O1 Mn1 O1 114.08(10) 3_566 2_556 ? O1 Mn1 O1 167.86(13) . 2_556 ? O2 Mn1 Mn1 120.64(8) 1_455 3_567 ? O2 Mn1 Mn1 90.93(8) 2_656 3_567 ? O1 Mn1 Mn1 38.66(7) 4_566 3_567 ? O1 Mn1 Mn1 98.14(7) 3_566 3_567 ? O1 Mn1 Mn1 152.15(7) . 3_567 ? O1 Mn1 Mn1 37.18(6) 2_556 3_567 ? O2 Mn1 Mn1 90.93(8) 1_455 3_566 ? O2 Mn1 Mn1 120.64(8) 2_656 3_566 ? O1 Mn1 Mn1 98.14(7) 4_566 3_566 ? O1 Mn1 Mn1 38.66(7) 3_566 3_566 ? O1 Mn1 Mn1 37.18(6) . 3_566 ? O1 Mn1 Mn1 152.15(7) 2_556 3_566 ? Mn1 Mn1 Mn1 131.14(5) 3_567 3_566 ? C1 O1 Mn1 128.6(2) . 3_566 ? C1 O1 Mn1 126.1(2) . . ? Mn1 O1 Mn1 104.15(10) 3_566 . ? C1 O2 Mn1 131.5(2) . 1_655 ? O2 C1 O1 123.0(3) . . ? O2 C1 C2 116.7(3) . . ? O1 C1 C2 120.2(3) . . ? C3 C2 C2 118.7(2) . 2 ? C3 C2 C1 115.9(3) . . ? C2 C2 C1 125.32(18) 2 . ? C4 C3 C2 121.7(4) . . ? C4 C3 H3A 119.2 . . ? C2 C3 H3A 119.1 . . ? C4 C4 C3 119.5(2) 2 . ? C4 C4 H4A 120.3 2 . ? C3 C4 H4A 120.2 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.162 _refine_diff_density_min -0.487 _refine_diff_density_rms 0.132 _database_code_depnum_ccdc_archive 'CCDC 913354' ####################################################################### # # 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 #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H4 Cu N0 O4' _chemical_formula_weight 227.65 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' Cu Cu 0.3201 1.2651 '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 13.171(5) _cell_length_b 5.1292(18) _cell_length_c 11.719(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.745(6) _cell_angle_gamma 90.00 _cell_volume 740.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description strip _exptl_crystal_colour green _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.042 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 2.920 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.618 _exptl_absorpt_correction_T_max 0.792 _exptl_absorpt_process_details ? _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 '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 3523 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1293 _reflns_number_gt 1112 _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^)+(0.0653P)^2^+0.5533P] 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 geom _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1293 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1106 _refine_ls_wR_factor_gt 0.1070 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 Cu1 Cu 0.53790(4) 1.21454(10) 0.56114(5) 0.0192(2) Uani 1 1 d . . . O2 O 0.6456(3) 1.1999(6) 0.4839(3) 0.0291(8) Uani 1 1 d . . . O1 O 0.4217(3) 1.1603(6) 0.6258(3) 0.0269(8) Uani 1 1 d . . . O4 O 0.4313(2) 1.3654(6) 0.4039(3) 0.0234(7) Uani 1 1 d . . . O3 O 0.6391(3) 1.0044(6) 0.6915(3) 0.0258(8) Uani 1 1 d . . . C1 C 0.7352(4) 0.6121(9) 0.7600(4) 0.0208(10) Uani 1 1 d . . . C6 C 0.7381(4) 0.4724(9) 0.8633(4) 0.0225(10) Uani 1 1 d . . . C4 C 0.9162(4) 0.3112(11) 0.8853(5) 0.0395(14) Uani 1 1 d . . . H4A H 0.9766 0.2104 0.9271 0.047 Uiso 1 1 calc R . . C5 C 0.8294(4) 0.3195(10) 0.9243(5) 0.0317(12) Uani 1 1 d . . . H5A H 0.8313 0.2224 0.9920 0.038 Uiso 1 1 calc R . . C2 C 0.8238(4) 0.6020(10) 0.7223(5) 0.0317(12) Uani 1 1 d . . . H2A H 0.8225 0.6977 0.6544 0.038 Uiso 1 1 calc R . . C3 C 0.9138(4) 0.4531(11) 0.7835(5) 0.0405(14) Uani 1 1 d . . . H3A H 0.9724 0.4478 0.7568 0.049 Uiso 1 1 calc R . . C8 C 0.6395(4) 0.7626(8) 0.6795(4) 0.0209(10) Uani 1 1 d . . . C7 C 0.3534(4) 0.9774(9) 0.5907(4) 0.0212(10) 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 Cu1 0.0275(4) 0.0112(3) 0.0171(4) -0.0006(2) 0.0057(3) -0.0009(2) O2 0.034(2) 0.0258(19) 0.029(2) -0.0078(15) 0.0129(16) -0.0029(14) O1 0.0334(19) 0.0239(19) 0.0251(19) -0.0048(15) 0.0127(15) -0.0055(15) O4 0.0306(18) 0.0162(17) 0.0179(17) -0.0019(13) 0.0017(14) -0.0029(13) O3 0.0326(19) 0.0169(19) 0.0210(18) 0.0000(14) 0.0009(15) -0.0005(13) C1 0.027(3) 0.016(2) 0.015(2) -0.0054(18) 0.0029(19) -0.0039(18) C6 0.028(3) 0.019(2) 0.019(2) -0.0010(19) 0.006(2) -0.0013(18) C4 0.032(3) 0.040(3) 0.041(3) 0.013(3) 0.007(3) 0.014(2) C5 0.036(3) 0.032(3) 0.025(3) 0.014(2) 0.008(2) 0.006(2) C2 0.035(3) 0.036(3) 0.028(3) 0.006(2) 0.015(2) 0.000(2) C3 0.029(3) 0.047(4) 0.048(4) 0.009(3) 0.017(3) 0.006(2) C8 0.027(3) 0.018(3) 0.020(3) -0.0009(19) 0.011(2) -0.0039(18) C7 0.025(2) 0.022(3) 0.013(2) 0.0025(19) 0.0022(19) 0.0038(18) _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 Cu1 O2 1.935(3) . ? Cu1 O1 1.953(3) . ? Cu1 O3 1.957(3) . ? Cu1 O4 2.033(3) . ? Cu1 O4 2.204(3) 3_686 ? Cu1 Cu1 2.6229(12) 3_676 ? O2 C7 1.265(5) 3_676 ? O1 C7 1.264(5) . ? O4 C8 1.269(6) 3_676 ? O4 Cu1 2.204(3) 3_686 ? O3 C8 1.248(5) . ? C1 C2 1.387(6) . ? C1 C6 1.395(6) . ? C1 C8 1.495(6) . ? C6 C5 1.401(7) . ? C6 C7 1.485(6) 2_646 ? C4 C5 1.374(7) . ? C4 C3 1.388(8) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C2 C3 1.378(7) . ? C2 H2A 0.9300 . ? C3 H3A 0.9300 . ? C8 O4 1.269(6) 3_676 ? C7 O2 1.265(5) 3_676 ? C7 C6 1.485(6) 2_656 ? 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 Cu1 O1 168.68(14) . . ? O2 Cu1 O3 86.24(14) . . ? O1 Cu1 O3 91.67(14) . . ? O2 Cu1 O4 88.61(14) . . ? O1 Cu1 O4 91.25(13) . . ? O3 Cu1 O4 167.96(13) . . ? O2 Cu1 O4 90.46(13) . 3_686 ? O1 Cu1 O4 100.65(13) . 3_686 ? O3 Cu1 O4 111.33(12) . 3_686 ? O4 Cu1 O4 79.56(13) . 3_686 ? O2 Cu1 Cu1 84.96(10) . 3_676 ? O1 Cu1 Cu1 83.89(10) . 3_676 ? O3 Cu1 Cu1 89.23(9) . 3_676 ? O4 Cu1 Cu1 79.48(9) . 3_676 ? O4 Cu1 Cu1 158.63(9) 3_686 3_676 ? C7 O2 Cu1 122.7(3) 3_676 . ? C7 O1 Cu1 123.0(3) . . ? C8 O4 Cu1 125.7(3) 3_676 . ? C8 O4 Cu1 133.3(3) 3_676 3_686 ? Cu1 O4 Cu1 100.44(13) . 3_686 ? C8 O3 Cu1 119.2(3) . . ? C2 C1 C6 119.3(4) . . ? C2 C1 C8 115.8(4) . . ? C6 C1 C8 124.8(4) . . ? C1 C6 C5 119.0(4) . . ? C1 C6 C7 122.0(4) . 2_646 ? C5 C6 C7 119.0(4) . 2_646 ? C5 C4 C3 120.1(5) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? C4 C5 C6 120.8(5) . . ? C4 C5 H5A 119.6 . . ? C6 C5 H5A 119.6 . . ? C3 C2 C1 121.3(5) . . ? C3 C2 H2A 119.3 . . ? C1 C2 H2A 119.3 . . ? C2 C3 C4 119.4(5) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? O3 C8 O4 124.7(4) . 3_676 ? O3 C8 C1 118.6(4) . . ? O4 C8 C1 116.4(4) 3_676 . ? O1 C7 O2 125.3(4) . 3_676 ? O1 C7 C6 118.1(4) . 2_656 ? O2 C7 C6 116.6(4) 3_676 2_656 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.357 _refine_diff_density_min -0.781 _refine_diff_density_rms 0.116 _database_code_depnum_ccdc_archive 'CCDC 913355' ####################################################################### # # 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_3 #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H10 Co3 O10' _chemical_formula_weight 539.03 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' 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 11.648(2) _cell_length_b 12.091(3) _cell_length_c 11.846(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.245(4) _cell_angle_gamma 90.00 _cell_volume 1624.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description strip _exptl_crystal_colour purple _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1068 _exptl_absorpt_coefficient_mu 3.090 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.430 _exptl_absorpt_correction_T_max 0.857 _exptl_absorpt_process_details ? _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 '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 7928 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0515 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2846 _reflns_number_gt 2074 _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^)+(0.0722P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2846 _refine_ls_number_parameters 272 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.1045 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _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 0.00015(7) 0.25035(4) 0.37968(5) 0.02118(19) Uani 1 1 d . . . Co2 Co -0.08571(5) -0.00031(4) 0.23099(5) 0.01822(19) Uani 1 1 d . . . Co3 Co 0.0000 0.5000 0.5000 0.0185(2) Uani 1 2 d S . . Co4 Co 0.0000 0.0000 0.5000 0.0193(2) Uani 1 2 d S . . O1 O 0.1265(3) -0.1946(3) 0.2607(3) 0.0313(8) Uani 1 1 d . . . O2 O 0.0572(3) -0.0627(2) 0.3577(2) 0.0231(7) Uani 1 1 d . . . O3 O 0.1075(3) -0.3589(2) 0.5170(3) 0.0241(7) Uani 1 1 d . . . O4 O 0.2099(3) -0.4045(2) 0.3856(3) 0.0253(7) Uani 1 1 d . . . O5 O 0.0574(3) 0.0616(2) 0.1692(2) 0.0220(7) Uani 1 1 d . . . O6 O 0.1247(3) 0.1968(3) 0.2935(3) 0.0328(8) Uani 1 1 d . . . O7 O 0.2122(3) 0.4052(2) 0.2096(3) 0.0255(7) Uani 1 1 d . . . O8 O 0.1106(3) 0.3590(2) 0.0322(3) 0.0269(8) Uani 1 1 d . . . O9 O 0.0877(3) 0.3943(2) 0.4084(2) 0.0197(7) Uani 1 1 d D . . H9 H 0.1599(14) 0.388(4) 0.442(4) 0.024 Uiso 1 1 d D . . O10 O -0.0865(3) 0.1061(2) 0.3696(2) 0.0192(7) Uani 1 1 d D . . H10 H -0.1589(13) 0.116(3) 0.368(4) 0.017(13) Uiso 1 1 d D . . C1 C 0.1337(4) -0.1343(3) 0.3454(4) 0.0197(10) Uani 1 1 d . . . C2 C 0.2404(4) -0.1441(3) 0.4433(3) 0.0190(10) Uani 1 1 d . . . C3 C 0.3093(4) -0.0523(4) 0.4824(4) 0.0274(11) Uani 1 1 d . . . H3A H 0.2910 0.0156 0.4459 0.033 Uiso 1 1 calc R . . C4 C 0.4049(5) -0.0614(4) 0.5749(4) 0.0355(13) Uani 1 1 d . . . H4A H 0.4527 -0.0003 0.5994 0.043 Uiso 1 1 calc R . . C5 C 0.4294(5) -0.1613(4) 0.6308(4) 0.0390(13) Uani 1 1 d . . . H5A H 0.4943 -0.1676 0.6929 0.047 Uiso 1 1 calc R . . C6 C 0.3594(5) -0.2510(4) 0.5961(4) 0.0301(12) Uani 1 1 d . . . H6A H 0.3750 -0.3169 0.6371 0.036 Uiso 1 1 calc R . . C7 C 0.2655(4) -0.2452(3) 0.5005(4) 0.0173(10) Uani 1 1 d . . . C8 C 0.1897(4) -0.3431(4) 0.4632(4) 0.0214(10) Uani 1 1 d . . . C9 C 0.1324(4) 0.1346(4) 0.2131(4) 0.0221(10) Uani 1 1 d . . . C10 C 0.2391(4) 0.1440(3) 0.1646(4) 0.0202(10) Uani 1 1 d . . . C11 C 0.3068(4) 0.0505(4) 0.1562(4) 0.0248(11) Uani 1 1 d . . . H11A H 0.2868 -0.0173 0.1833 0.030 Uiso 1 1 calc R . . C12 C 0.4037(5) 0.0584(4) 0.1075(4) 0.0349(13) Uani 1 1 d . . . H12A H 0.4497 -0.0038 0.1040 0.042 Uiso 1 1 calc R . . C13 C 0.4320(5) 0.1567(4) 0.0649(5) 0.0421(14) Uani 1 1 d . . . H13A H 0.4968 0.1616 0.0315 0.050 Uiso 1 1 calc R . . C14 C 0.3645(5) 0.2486(4) 0.0713(5) 0.0334(13) Uani 1 1 d . . . H14A H 0.3839 0.3151 0.0410 0.040 Uiso 1 1 calc R . . C15 C 0.2685(4) 0.2449(3) 0.1215(4) 0.0200(10) Uani 1 1 d . . . C16 C 0.1920(4) 0.3443(4) 0.1226(4) 0.0226(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0335(4) 0.0155(3) 0.0160(3) -0.0007(2) 0.0088(3) -0.0028(3) Co2 0.0307(4) 0.0171(3) 0.0085(3) -0.0001(2) 0.0077(2) 0.0000(3) Co3 0.0308(5) 0.0157(4) 0.0107(4) -0.0007(3) 0.0084(4) -0.0008(4) Co4 0.0338(5) 0.0153(4) 0.0101(4) 0.0011(3) 0.0074(4) -0.0010(4) O1 0.045(2) 0.0248(18) 0.0205(18) -0.0065(15) 0.0005(15) 0.0073(16) O2 0.0319(19) 0.0266(18) 0.0117(15) 0.0003(14) 0.0068(13) 0.0074(15) O3 0.038(2) 0.0223(16) 0.0154(16) -0.0038(13) 0.0134(14) -0.0063(14) O4 0.036(2) 0.0244(17) 0.0166(17) -0.0064(14) 0.0092(14) -0.0046(15) O5 0.0290(19) 0.0260(18) 0.0131(16) -0.0024(14) 0.0090(13) -0.0072(14) O6 0.051(2) 0.0242(18) 0.031(2) -0.0123(16) 0.0254(17) -0.0115(16) O7 0.035(2) 0.0268(18) 0.0159(17) -0.0029(14) 0.0080(14) 0.0047(15) O8 0.041(2) 0.0246(17) 0.0146(17) -0.0027(14) 0.0061(14) 0.0070(15) O9 0.0278(18) 0.0180(15) 0.0141(16) -0.0012(13) 0.0062(13) 0.0008(14) O10 0.0240(19) 0.0204(16) 0.0162(16) -0.0005(13) 0.0106(13) -0.0005(14) C1 0.032(3) 0.018(2) 0.012(2) 0.0048(18) 0.0097(19) -0.0038(19) C2 0.025(3) 0.022(2) 0.011(2) -0.0009(18) 0.0067(18) -0.0024(19) C3 0.037(3) 0.018(2) 0.028(3) 0.001(2) 0.009(2) -0.003(2) C4 0.045(3) 0.025(3) 0.035(3) -0.008(2) 0.004(2) -0.012(2) C5 0.040(3) 0.038(3) 0.031(3) -0.001(2) -0.009(2) -0.005(3) C6 0.036(3) 0.023(3) 0.028(3) 0.005(2) 0.001(2) 0.002(2) C7 0.023(3) 0.019(2) 0.011(2) 0.0004(17) 0.0057(18) -0.0008(18) C8 0.034(3) 0.019(2) 0.010(2) 0.0017(19) 0.0032(19) 0.001(2) C9 0.034(3) 0.021(2) 0.014(2) 0.0017(19) 0.010(2) 0.001(2) C10 0.027(3) 0.022(2) 0.011(2) -0.0038(18) 0.0045(18) 0.0004(19) C11 0.032(3) 0.020(2) 0.023(3) -0.001(2) 0.007(2) -0.002(2) C12 0.045(3) 0.025(3) 0.039(3) -0.003(2) 0.018(3) 0.008(2) C13 0.051(4) 0.037(3) 0.048(4) 0.001(3) 0.032(3) 0.002(3) C14 0.043(4) 0.021(3) 0.045(3) 0.004(2) 0.027(3) 0.000(2) C15 0.028(3) 0.020(2) 0.013(2) -0.0016(18) 0.0082(19) -0.0009(18) C16 0.034(3) 0.019(2) 0.018(3) 0.004(2) 0.013(2) 0.001(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 Co1 O10 2.005(3) . ? Co1 O9 2.007(3) . ? Co1 O6 2.060(3) . ? Co1 O1 2.064(3) 2 ? Co1 O3 2.345(3) 3_556 ? Co1 O8 2.367(3) 4_566 ? Co2 O9 2.082(3) 2_545 ? Co2 O10 2.088(3) . ? Co2 O4 2.104(3) 2 ? Co2 O5 2.106(3) . ? Co2 O7 2.109(3) 2_545 ? Co2 O2 2.109(3) . ? Co3 O9 2.088(3) 3_566 ? Co3 O9 2.088(3) . ? Co3 O5 2.098(3) 2 ? Co3 O5 2.098(3) 4_566 ? Co3 O3 2.099(3) 1_565 ? Co3 O3 2.099(3) 3_556 ? Co4 O10 2.082(3) . ? Co4 O10 2.082(3) 3_556 ? Co4 O2 2.091(3) 3_556 ? Co4 O2 2.091(3) . ? Co4 O8 2.118(3) 4_566 ? Co4 O8 2.118(3) 2_545 ? O1 C1 1.228(5) . ? O1 Co1 2.064(3) 2_545 ? O2 C1 1.275(5) . ? O3 C8 1.280(5) . ? O3 Co3 2.099(3) 1_545 ? O3 Co1 2.345(3) 3_556 ? O4 C8 1.245(5) . ? O4 Co2 2.104(3) 2_545 ? O5 C9 1.267(5) . ? O5 Co3 2.098(3) 2_545 ? O6 C9 1.233(5) . ? O7 C16 1.244(5) . ? O7 Co2 2.109(3) 2 ? O8 C16 1.269(5) . ? O8 Co4 2.118(3) 2 ? O8 Co1 2.367(3) 4_565 ? O9 Co2 2.082(3) 2 ? O9 H9 0.849(10) . ? O10 H10 0.848(10) . ? C1 C2 1.498(6) . ? C2 C3 1.385(6) . ? C2 C7 1.396(6) . ? C3 C4 1.376(7) . ? C3 H3A 0.9300 . ? C4 C5 1.376(7) . ? C4 H4A 0.9300 . ? C5 C6 1.362(7) . ? C5 H5A 0.9300 . ? C6 C7 1.384(7) . ? C6 H6A 0.9300 . ? C7 C8 1.482(6) . ? C9 C10 1.489(6) . ? C10 C11 1.395(6) . ? C10 C15 1.395(6) . ? C11 C12 1.383(7) . ? C11 H11A 0.9300 . ? C12 C13 1.361(7) . ? C12 H12A 0.9300 . ? C13 C14 1.373(7) . ? C13 H13A 0.9300 . ? C14 C15 1.383(7) . ? C14 H14A 0.9300 . ? C15 C16 1.498(6) . ? 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 O10 Co1 O9 173.73(12) . . ? O10 Co1 O6 95.72(12) . . ? O9 Co1 O6 88.19(12) . . ? O10 Co1 O1 88.58(13) . 2 ? O9 Co1 O1 95.66(13) . 2 ? O6 Co1 O1 99.01(14) . 2 ? O10 Co1 O3 101.28(11) . 3_556 ? O9 Co1 O3 74.79(11) . 3_556 ? O6 Co1 O3 162.97(12) . 3_556 ? O1 Co1 O3 82.59(13) 2 3_556 ? O10 Co1 O8 74.81(12) . 4_566 ? O9 Co1 O8 100.88(12) . 4_566 ? O6 Co1 O8 83.18(13) . 4_566 ? O1 Co1 O8 163.38(12) 2 4_566 ? O3 Co1 O8 100.17(11) 3_556 4_566 ? O9 Co2 O10 179.07(12) 2_545 . ? O9 Co2 O4 86.27(12) 2_545 2 ? O10 Co2 O4 92.91(12) . 2 ? O9 Co2 O5 78.87(11) 2_545 . ? O10 Co2 O5 101.61(11) . . ? O4 Co2 O5 93.22(12) 2 . ? O9 Co2 O7 92.99(12) 2_545 2_545 ? O10 Co2 O7 86.66(12) . 2_545 ? O4 Co2 O7 95.13(12) 2 2_545 ? O5 Co2 O7 167.93(12) . 2_545 ? O9 Co2 O2 102.09(12) 2_545 . ? O10 Co2 O2 78.79(12) . . ? O4 Co2 O2 167.42(12) 2 . ? O5 Co2 O2 79.39(12) . . ? O7 Co2 O2 93.81(12) 2_545 . ? O9 Co3 O9 180.00(12) 3_566 . ? O9 Co3 O5 101.08(11) 3_566 2 ? O9 Co3 O5 78.92(11) . 2 ? O9 Co3 O5 78.92(11) 3_566 4_566 ? O9 Co3 O5 101.08(11) . 4_566 ? O5 Co3 O5 180.0 2 4_566 ? O9 Co3 O3 78.76(12) 3_566 1_565 ? O9 Co3 O3 101.24(12) . 1_565 ? O5 Co3 O3 81.72(12) 2 1_565 ? O5 Co3 O3 98.28(12) 4_566 1_565 ? O9 Co3 O3 101.24(12) 3_566 3_556 ? O9 Co3 O3 78.76(12) . 3_556 ? O5 Co3 O3 98.28(12) 2 3_556 ? O5 Co3 O3 81.72(12) 4_566 3_556 ? O3 Co3 O3 180.0 1_565 3_556 ? O10 Co4 O10 180.00(13) . 3_556 ? O10 Co4 O2 100.67(11) . 3_556 ? O10 Co4 O2 79.33(11) 3_556 3_556 ? O10 Co4 O2 79.33(11) . . ? O10 Co4 O2 100.67(11) 3_556 . ? O2 Co4 O2 180.00(8) 3_556 . ? O10 Co4 O8 78.96(12) . 4_566 ? O10 Co4 O8 101.04(12) 3_556 4_566 ? O2 Co4 O8 81.73(12) 3_556 4_566 ? O2 Co4 O8 98.27(12) . 4_566 ? O10 Co4 O8 101.04(12) . 2_545 ? O10 Co4 O8 78.96(12) 3_556 2_545 ? O2 Co4 O8 98.27(12) 3_556 2_545 ? O2 Co4 O8 81.73(12) . 2_545 ? O8 Co4 O8 180.00(9) 4_566 2_545 ? C1 O1 Co1 138.8(3) . 2_545 ? C1 O2 Co4 134.3(3) . . ? C1 O2 Co2 128.3(3) . . ? Co4 O2 Co2 95.68(12) . . ? C8 O3 Co3 124.8(3) . 1_545 ? C8 O3 Co1 136.6(3) . 3_556 ? Co3 O3 Co1 97.25(12) 1_545 3_556 ? C8 O4 Co2 126.5(3) . 2_545 ? C9 O5 Co3 132.8(3) . 2_545 ? C9 O5 Co2 129.1(3) . . ? Co3 O5 Co2 95.83(12) 2_545 . ? C9 O6 Co1 139.3(3) . . ? C16 O7 Co2 125.6(3) . 2 ? C16 O8 Co4 124.7(3) . 2 ? C16 O8 Co1 137.4(3) . 4_565 ? Co4 O8 Co1 96.34(13) 2 4_565 ? Co1 O9 Co2 118.90(14) . 2 ? Co1 O9 Co3 109.21(14) . . ? Co2 O9 Co3 96.90(12) 2 . ? Co1 O9 H9 114(3) . . ? Co2 O9 H9 105(3) 2 . ? Co3 O9 H9 111(3) . . ? Co1 O10 Co4 109.90(14) . . ? Co1 O10 Co2 119.34(14) . . ? Co4 O10 Co2 96.60(12) . . ? Co1 O10 H10 111(3) . . ? Co4 O10 H10 115(3) . . ? Co2 O10 H10 105(3) . . ? O1 C1 O2 125.4(4) . . ? O1 C1 C2 118.4(4) . . ? O2 C1 C2 116.3(4) . . ? C3 C2 C7 119.9(4) . . ? C3 C2 C1 120.7(4) . . ? C7 C2 C1 119.2(4) . . ? C4 C3 C2 120.3(4) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C5 C4 C3 119.6(5) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C6 C5 C4 120.7(5) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C5 C6 C7 120.8(4) . . ? C5 C6 H6A 119.6 . . ? C7 C6 H6A 119.6 . . ? C6 C7 C2 118.7(4) . . ? C6 C7 C8 120.6(4) . . ? C2 C7 C8 120.7(4) . . ? O4 C8 O3 124.6(4) . . ? O4 C8 C7 119.8(4) . . ? O3 C8 C7 115.6(4) . . ? O6 C9 O5 125.3(4) . . ? O6 C9 C10 117.8(4) . . ? O5 C9 C10 116.9(4) . . ? C11 C10 C15 119.5(4) . . ? C11 C10 C9 120.1(4) . . ? C15 C10 C9 120.3(4) . . ? C12 C11 C10 120.2(4) . . ? C12 C11 H11A 119.9 . . ? C10 C11 H11A 119.9 . . ? C13 C12 C11 120.3(5) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C12 C13 C14 119.7(5) . . ? C12 C13 H13A 120.1 . . ? C14 C13 H13A 120.1 . . ? C13 C14 C15 121.9(4) . . ? C13 C14 H14A 119.1 . . ? C15 C14 H14A 119.1 . . ? C14 C15 C10 118.4(4) . . ? C14 C15 C16 121.3(4) . . ? C10 C15 C16 120.1(4) . . ? O7 C16 O8 125.4(4) . . ? O7 C16 C15 118.8(4) . . ? O8 C16 C15 115.8(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.394 _refine_diff_density_min -0.757 _refine_diff_density_rms 0.136 _database_code_depnum_ccdc_archive 'CCDC 913356'