Supplementary Material (ESI) for CrystEngComm This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Fabrizia Grepioni' 'Dario Braga' 'Lucia Maini' 'Michele Mazzotti' 'Katia Rubini' _publ_contact_author_name 'Prof Fabrizia Grepioni' _publ_contact_author_address ; Dipartimento di Chimica University of Sassari Via Vienna 2 Sassari 07100 ITALY ; _publ_contact_author_email GREPIONI@SSMAIN.UNISS.IT _publ_section_title ; Reversible gas-solid reactions between the organometallic zwitterion [CoIII(h5-C5H4COOH)(h5-C5H4COO)] and vapours of difluoro and chloro acetic acids ; data_2-[HCF2COO] _database_code_CSD 204245 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 Co F2 O6' _chemical_formula_weight 372.16 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' F F 0.0171 0.0103 '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 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 12.588(3) _cell_length_b 11.726(2) _cell_length_c 8.9870(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1326.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.863 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 1.350 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min 0.7243 _exptl_absorpt_correction_T_max 1.0000 _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 2103 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2012 _reflns_number_gt 1368 _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^)+(0.0914P)^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 2012 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1311 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.16956(3) 0.2500 0.50014(5) 0.02036(15) Uani 1 2 d S . . C1 C 0.21340(19) 0.1097(2) 0.6197(3) 0.0271(4) Uani 1 1 d . . . H1A H 0.2511 0.1099 0.7151 0.033 Uiso 1 1 calc R . . C2 C 0.1018(2) 0.1120(2) 0.5998(3) 0.0322(5) Uani 1 1 d . . . H2A H 0.0488 0.1145 0.6797 0.039 Uiso 1 1 calc R . . C3 C 0.07965(19) 0.1112(2) 0.4454(3) 0.0325(5) Uani 1 1 d . . . H3A H 0.0089 0.1129 0.3999 0.039 Uiso 1 1 calc R . . C4 C 0.17793(18) 0.1086(2) 0.3682(3) 0.0291(5) Uani 1 1 d . . . H4A H 0.1871 0.1081 0.2599 0.035 Uiso 1 1 calc R . . C5 C 0.26102(18) 0.10766(19) 0.4758(3) 0.0242(4) Uani 1 1 d . . . C6 C 0.37636(18) 0.1118(2) 0.4382(3) 0.0301(5) Uani 1 1 d . . . C7 C 0.6789(3) 0.2500 0.5089(4) 0.0283(7) Uani 1 2 d S . . C8 C 0.7997(3) 0.2500 0.4898(4) 0.0309(7) Uani 1 2 d S . . H8A H 0.8175 0.2500 0.3836 0.037 Uiso 1 2 calc SR . . O1 O 0.43649(15) 0.11659(19) 0.5569(2) 0.0407(5) Uani 1 1 d . . . O2 O 0.40555(17) 0.1111(2) 0.3115(2) 0.0508(6) Uani 1 1 d . . . O3 O 0.63674(18) 0.1546(2) 0.5135(3) 0.0491(6) Uani 1 1 d . . . F1 F 0.84346(14) 0.15811(19) 0.5560(3) 0.0613(6) Uani 1 1 d . . . H100 H 0.501(3) 0.122(3) 0.528(3) 0.044(9) Uiso 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 0.0188(2) 0.0171(2) 0.0251(2) 0.000 -0.00063(15) 0.000 C1 0.0322(11) 0.0233(10) 0.0259(10) 0.0050(9) -0.0012(8) 0.0010(9) C2 0.0295(10) 0.0264(10) 0.0406(12) 0.0080(10) 0.0062(10) -0.0036(9) C3 0.0271(11) 0.0216(10) 0.0487(14) -0.0008(11) -0.0064(10) -0.0049(9) C4 0.0356(12) 0.0212(10) 0.0304(11) -0.0026(9) -0.0053(9) -0.0014(9) C5 0.0242(10) 0.0167(8) 0.0317(12) 0.0003(8) 0.0004(8) 0.0023(8) C6 0.0255(11) 0.0213(9) 0.0436(13) 0.0013(11) 0.0008(10) 0.0031(9) C7 0.0197(14) 0.0375(18) 0.0276(16) 0.000 0.0002(12) 0.000 C8 0.0231(15) 0.0340(17) 0.0354(18) 0.000 0.0030(13) 0.000 O1 0.0239(8) 0.0487(11) 0.0496(12) -0.0038(11) -0.0010(8) 0.0001(8) O2 0.0415(11) 0.0654(14) 0.0456(11) 0.0043(11) 0.0160(9) 0.0093(11) O3 0.0277(9) 0.0369(10) 0.0826(17) 0.0001(10) 0.0006(9) -0.0049(9) F1 0.0317(9) 0.0562(12) 0.0961(16) 0.0307(13) 0.0075(9) 0.0128(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 C2 2.037(2) 7_565 ? Co1 C2 2.037(2) . ? Co1 C5 2.039(2) 7_565 ? Co1 C5 2.039(2) . ? Co1 C4 2.041(2) 7_565 ? Co1 C4 2.041(2) . ? Co1 C1 2.041(2) 7_565 ? Co1 C1 2.041(2) . ? Co1 C3 2.042(2) . ? Co1 C3 2.042(2) 7_565 ? C1 C2 1.416(3) . ? C1 C5 1.425(3) . ? C1 H1A 0.9800 . ? C2 C3 1.415(4) . ? C2 H2A 0.9800 . ? C3 C4 1.419(3) . ? C3 H3A 0.9800 . ? C4 C5 1.424(3) . ? C4 H4A 0.9800 . ? C5 C6 1.492(3) . ? C6 O2 1.196(3) . ? C6 O1 1.309(3) . ? C7 O3 1.239(3) 7_565 ? C7 O3 1.239(3) . ? C7 C8 1.530(5) . ? C8 F1 1.349(3) 7_565 ? C8 F1 1.349(3) . ? C8 H8A 0.9800 . ? O1 H100 0.85(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 C2 Co1 C2 105.19(15) 7_565 . ? C2 Co1 C5 68.50(10) 7_565 7_565 ? C2 Co1 C5 159.02(10) . 7_565 ? C2 Co1 C5 159.02(10) 7_565 . ? C2 Co1 C5 68.50(10) . . ? C5 Co1 C5 109.85(13) 7_565 . ? C2 Co1 C4 68.40(11) 7_565 7_565 ? C2 Co1 C4 157.30(10) . 7_565 ? C5 Co1 C4 40.87(9) 7_565 7_565 ? C5 Co1 C4 124.99(10) . 7_565 ? C2 Co1 C4 157.30(10) 7_565 . ? C2 Co1 C4 68.40(11) . . ? C5 Co1 C4 124.99(10) 7_565 . ? C5 Co1 C4 40.87(9) . . ? C4 Co1 C4 108.66(14) 7_565 . ? C2 Co1 C1 40.66(10) 7_565 7_565 ? C2 Co1 C1 121.47(10) . 7_565 ? C5 Co1 C1 40.89(9) 7_565 7_565 ? C5 Co1 C1 124.29(9) . 7_565 ? C4 Co1 C1 68.71(10) 7_565 7_565 ? C4 Co1 C1 161.19(10) . 7_565 ? C2 Co1 C1 121.47(10) 7_565 . ? C2 Co1 C1 40.66(10) . . ? C5 Co1 C1 124.29(9) 7_565 . ? C5 Co1 C1 40.89(9) . . ? C4 Co1 C1 161.19(10) 7_565 . ? C4 Co1 C1 68.71(10) . . ? C1 Co1 C1 107.43(13) 7_565 . ? C2 Co1 C3 120.45(10) 7_565 . ? C2 Co1 C3 40.61(11) . . ? C5 Co1 C3 159.92(11) 7_565 . ? C5 Co1 C3 68.59(10) . . ? C4 Co1 C3 122.42(10) 7_565 . ? C4 Co1 C3 40.66(10) . . ? C1 Co1 C3 156.77(11) 7_565 . ? C1 Co1 C3 68.55(10) . . ? C2 Co1 C3 40.61(11) 7_565 7_565 ? C2 Co1 C3 120.45(10) . 7_565 ? C5 Co1 C3 68.59(10) 7_565 7_565 ? C5 Co1 C3 159.92(11) . 7_565 ? C4 Co1 C3 40.66(10) 7_565 7_565 ? C4 Co1 C3 122.42(10) . 7_565 ? C1 Co1 C3 68.55(10) 7_565 7_565 ? C1 Co1 C3 156.77(11) . 7_565 ? C3 Co1 C3 105.66(14) . 7_565 ? C2 C1 C5 107.7(2) . . ? C2 C1 Co1 69.52(14) . . ? C5 C1 Co1 69.51(12) . . ? C2 C1 H1A 126.2 . . ? C5 C1 H1A 126.2 . . ? Co1 C1 H1A 126.2 . . ? C3 C2 C1 108.6(2) . . ? C3 C2 Co1 69.90(13) . . ? C1 C2 Co1 69.82(14) . . ? C3 C2 H2A 125.7 . . ? C1 C2 H2A 125.7 . . ? Co1 C2 H2A 125.7 . . ? C2 C3 C4 107.9(2) . . ? C2 C3 Co1 69.49(14) . . ? C4 C3 Co1 69.62(13) . . ? C2 C3 H3A 126.0 . . ? C4 C3 H3A 126.0 . . ? Co1 C3 H3A 126.0 . . ? C3 C4 C5 108.0(2) . . ? C3 C4 Co1 69.72(14) . . ? C5 C4 Co1 69.52(13) . . ? C3 C4 H4A 126.0 . . ? C5 C4 H4A 126.0 . . ? Co1 C4 H4A 126.0 . . ? C4 C5 C1 107.9(2) . . ? C4 C5 C6 124.1(2) . . ? C1 C5 C6 127.9(2) . . ? C4 C5 Co1 69.62(13) . . ? C1 C5 Co1 69.60(13) . . ? C6 C5 Co1 123.16(16) . . ? O2 C6 O1 126.7(2) . . ? O2 C6 C5 120.9(2) . . ? O1 C6 C5 112.3(2) . . ? O3 C7 O3 129.1(3) 7_565 . ? O3 C7 C8 115.44(17) 7_565 . ? O3 C7 C8 115.44(17) . . ? F1 C8 F1 106.0(3) 7_565 . ? F1 C8 C7 110.9(2) 7_565 . ? F1 C8 C7 110.9(2) . . ? F1 C8 H8A 109.7 7_565 . ? F1 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? C6 O1 H100 108(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.98 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.009 _refine_diff_density_min -0.762 _refine_diff_density_rms 0.114 data_2-[H2CFCOO] _database_code_CSD 204246 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Co F O6' _chemical_formula_weight 354.17 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.8330(16) _cell_length_b 11.696(2) _cell_length_c 14.435(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.13(3) _cell_angle_gamma 90.00 _cell_volume 1301.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.807 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 1.360 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min 0.7904 _exptl_absorpt_correction_T_max 1.0000 _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 2369 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2277 _reflns_number_gt 1621 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0930P)^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 2277 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1264 _refine_ls_wR_factor_gt 0.1115 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.001 _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 0.01082(5) 0.74846(4) 0.83915(3) 0.0211(2) Uani 1 1 d . . . C1 C -0.0343(3) 0.8944(2) 0.90784(13) 0.0295(8) Uani 1 1 d G . . H1A H -0.0702 0.8988 0.9694 0.035 Uiso 1 1 calc R . . C2 C -0.1466(2) 0.8890(2) 0.81928(17) 0.0341(8) Uani 1 1 d G . . H2A H -0.2736 0.8886 0.8090 0.041 Uiso 1 1 calc R . . C3 C -0.0424(3) 0.8833(2) 0.74821(12) 0.0377(9) Uani 1 1 d G . . H3A H -0.0850 0.8781 0.6803 0.045 Uiso 1 1 calc R . . C4 C 0.1342(3) 0.8852(2) 0.79285(15) 0.0326(8) Uani 1 1 d G . . H4A H 0.2349 0.8818 0.7612 0.039 Uiso 1 1 calc R . . C5 C 0.1393(2) 0.8920(2) 0.89151(14) 0.0258(7) Uani 1 1 d G . . C6 C 0.2935(5) 0.8886(3) 0.9686(3) 0.0301(8) Uani 1 1 d . . . O1 O 0.2772(3) 0.8936(3) 1.04954(18) 0.0416(7) Uani 1 1 d . . . O2 O 0.4383(3) 0.8779(2) 0.9364(2) 0.0375(7) Uani 1 1 d . . . C7 C 0.0264(3) 0.6124(2) 0.92860(11) 0.0275(7) Uani 1 1 d G . . H7A H 0.0431 0.6164 0.9974 0.033 Uiso 1 1 calc R . . C8 C -0.1355(2) 0.6119(2) 0.86624(16) 0.0338(8) Uani 1 1 d G . . H8A H -0.2501 0.6156 0.8845 0.041 Uiso 1 1 calc R . . C9 C -0.1021(2) 0.6062(2) 0.77280(13) 0.0310(8) Uani 1 1 d G . . H9A H -0.1896 0.6052 0.7152 0.037 Uiso 1 1 calc R . . C10 C 0.0805(3) 0.6031(2) 0.77742(13) 0.0284(8) Uani 1 1 d G . . H10A H 0.1411 0.5995 0.7236 0.034 Uiso 1 1 calc R . . C11 C 0.1598(2) 0.6070(2) 0.87371(15) 0.0248(7) Uani 1 1 d G . . C12 C 0.3497(4) 0.6116(3) 0.9085(2) 0.0266(8) Uani 1 1 d . . . O3 O 0.4524(3) 0.6064(2) 0.85505(19) 0.0402(7) Uani 1 1 d . . . O4 O 0.3887(3) 0.6241(2) 0.99958(18) 0.0369(7) Uani 1 1 d . . . C13 C 0.7723(4) 0.7528(3) 1.0882(2) 0.0261(8) Uani 1 1 d . . . C14 C 0.9509(5) 0.7606(3) 1.1493(3) 0.0348(9) Uani 1 1 d . . . H14A H 1.0276 0.8034 1.1161 0.042 Uiso 1 1 calc R . . H14B H 0.9425 0.8014 1.2068 0.042 Uiso 1 1 calc R . . O5 O 0.7092(3) 0.8489(2) 1.0626(2) 0.0406(7) Uani 1 1 d . . . O6 O 0.7066(3) 0.6573(2) 1.07005(19) 0.0396(7) Uani 1 1 d . . . F1 F 1.0198(3) 0.6536(2) 1.1714(2) 0.0654(8) Uani 1 1 d . . . H400 H 0.487(6) 0.629(4) 1.013(3) 0.046(14) Uiso 1 1 d . . . H200 H 0.518(6) 0.876(4) 0.986(3) 0.048(13) Uiso 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 0.0189(3) 0.0205(3) 0.0229(3) 0.00006(18) 0.00105(19) 0.00051(17) C1 0.0274(17) 0.0264(19) 0.0350(19) -0.0070(16) 0.0061(15) 0.0031(15) C2 0.0275(17) 0.0259(19) 0.045(2) -0.0005(18) -0.0042(16) 0.0091(16) C3 0.050(2) 0.027(2) 0.0310(19) 0.0078(17) -0.0052(17) 0.0026(18) C4 0.041(2) 0.0282(19) 0.0299(19) 0.0018(17) 0.0100(16) -0.0056(17) C5 0.0300(17) 0.0163(17) 0.0306(18) -0.0002(14) 0.0043(15) -0.0010(14) C6 0.0294(17) 0.0234(19) 0.037(2) -0.0042(16) 0.0057(15) -0.0016(15) O1 0.0378(15) 0.0581(19) 0.0276(14) -0.0059(13) 0.0024(11) 0.0008(13) O2 0.0247(13) 0.0450(16) 0.0426(16) -0.0015(14) 0.0060(12) -0.0032(12) C7 0.0287(17) 0.0244(18) 0.0316(18) 0.0026(16) 0.0111(14) -0.0010(15) C8 0.0253(17) 0.030(2) 0.048(2) 0.0026(18) 0.0109(16) -0.0054(15) C9 0.0332(19) 0.0224(18) 0.0337(19) -0.0044(16) -0.0044(15) -0.0036(16) C10 0.0338(19) 0.0217(18) 0.0303(18) -0.0031(15) 0.0076(15) 0.0000(15) C11 0.0219(16) 0.0206(18) 0.0318(18) 0.0011(15) 0.0048(14) 0.0027(14) C12 0.0269(17) 0.0232(19) 0.0299(19) 0.0028(15) 0.0053(15) 0.0037(14) O3 0.0250(12) 0.0576(18) 0.0412(15) -0.0023(14) 0.0143(12) 0.0039(13) O4 0.0249(14) 0.0498(17) 0.0336(15) -0.0003(13) -0.0012(12) -0.0003(13) C13 0.0207(18) 0.034(2) 0.0240(18) 0.0010(16) 0.0039(15) 0.0001(15) C14 0.0242(18) 0.045(3) 0.0322(19) -0.0012(17) -0.0034(15) -0.0014(15) O5 0.0279(13) 0.0399(17) 0.0509(17) 0.0013(13) -0.0014(12) 0.0034(12) O6 0.0290(13) 0.0390(17) 0.0468(16) -0.0004(13) -0.0042(12) -0.0031(12) F1 0.0518(15) 0.0536(17) 0.0775(19) 0.0047(14) -0.0249(13) 0.0134(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 C5 2.033(2) . ? Co1 C1 2.036(2) . ? Co1 C11 2.036(2) . ? Co1 C10 2.038(2) . ? Co1 C7 2.039(2) . ? Co1 C4 2.041(2) . ? Co1 C9 2.042(2) . ? Co1 C8 2.043(2) . ? Co1 C2 2.045(2) . ? Co1 C3 2.048(3) . ? C1 C2 1.4200 . ? C1 C5 1.4200 . ? C1 H1A 0.9800 . ? C2 C3 1.4200 . ? C2 H2A 0.9800 . ? C3 C4 1.4200 . ? C3 H3A 0.9800 . ? C4 C5 1.4200 . ? C4 H4A 0.9800 . ? C5 C6 1.492(4) . ? C6 O1 1.198(4) . ? C6 O2 1.306(4) . ? O2 H200 0.86(5) . ? C7 C8 1.4200 . ? C7 C11 1.4200 . ? C7 H7A 0.9800 . ? C8 C9 1.4200 . ? C8 H8A 0.9800 . ? C9 C10 1.4200 . ? C9 H9A 0.9800 . ? C10 C11 1.4200 . ? C10 H10A 0.9800 . ? C11 C12 1.485(4) . ? C12 O3 1.210(4) . ? C12 O4 1.304(4) . ? O4 H400 0.76(5) . ? C13 O6 1.238(4) . ? C13 O5 1.257(4) . ? C13 C14 1.519(5) . ? C14 F1 1.377(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? 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 C5 Co1 C1 40.8 . . ? C5 Co1 C11 110.80(9) . . ? C1 Co1 C11 134.68(9) . . ? C5 Co1 C10 134.29(9) . . ? C1 Co1 C10 174.34(9) . . ? C11 Co1 C10 40.8 . . ? C5 Co1 C7 116.00(9) . . ? C1 Co1 C7 110.00(9) . . ? C11 Co1 C7 40.8 . . ? C10 Co1 C7 68.61(5) . . ? C5 Co1 C4 40.8 . . ? C1 Co1 C4 68.61(6) . . ? C11 Co1 C4 115.65(9) . . ? C10 Co1 C4 109.37(9) . . ? C7 Co1 C4 147.11(10) . . ? C5 Co1 C9 172.86(10) . . ? C1 Co1 C9 144.47(9) . . ? C11 Co1 C9 68.59(6) . . ? C10 Co1 C9 40.7 . . ? C7 Co1 C9 68.52(6) . . ? C4 Co1 C9 132.52(10) . . ? C5 Co1 C8 146.28(9) . . ? C1 Co1 C8 114.27(9) . . ? C11 Co1 C8 68.57(6) . . ? C10 Co1 C8 68.53(6) . . ? C7 Co1 C8 40.7 . . ? C4 Co1 C8 171.50(10) . . ? C9 Co1 C8 40.7 . . ? C5 Co1 C2 68.58(6) . . ? C1 Co1 C2 40.7 . . ? C11 Co1 C2 173.46(10) . . ? C10 Co1 C2 144.16(9) . . ? C7 Co1 C2 133.13(10) . . ? C4 Co1 C2 68.44(6) . . ? C9 Co1 C2 112.89(9) . . ? C8 Co1 C2 108.11(9) . . ? C5 Co1 C3 68.52(6) . . ? C1 Co1 C3 68.48(6) . . ? C11 Co1 C3 145.75(10) . . ? C10 Co1 C3 113.72(9) . . ? C7 Co1 C3 171.79(10) . . ? C4 Co1 C3 40.6 . . ? C9 Co1 C3 107.73(9) . . ? C8 Co1 C3 131.83(10) . . ? C2 Co1 C3 40.6 . . ? C2 C1 C5 108.0 . . ? C2 C1 Co1 69.97(9) . . ? C5 C1 Co1 69.49(9) . . ? C2 C1 H1A 126.0 . . ? C5 C1 H1A 126.0 . . ? Co1 C1 H1A 126.0 . . ? C1 C2 C3 108.0 . . ? C1 C2 Co1 69.30(9) . . ? C3 C2 Co1 69.81(10) . . ? C1 C2 H2A 126.0 . . ? C3 C2 H2A 126.0 . . ? Co1 C2 H2A 126.0 . . ? C4 C3 C2 108.0 . . ? C4 C3 Co1 69.42(9) . . ? C2 C3 Co1 69.58(9) . . ? C4 C3 H3A 126.0 . . ? C2 C3 H3A 126.0 . . ? Co1 C3 H3A 126.0 . . ? C5 C4 C3 108.0 . . ? C5 C4 Co1 69.33(10) . . ? C3 C4 Co1 69.94(9) . . ? C5 C4 H4A 126.0 . . ? C3 C4 H4A 126.0 . . ? Co1 C4 H4A 126.0 . . ? C4 C5 C1 108.0 . . ? C4 C5 C6 128.5(2) . . ? C1 C5 C6 123.3(2) . . ? C4 C5 Co1 69.88(10) . . ? C1 C5 Co1 69.66(9) . . ? C6 C5 Co1 122.6(2) . . ? O1 C6 O2 126.8(4) . . ? O1 C6 C5 121.0(3) . . ? O2 C6 C5 112.2(3) . . ? C6 O2 H200 105(3) . . ? C8 C7 C11 108.0 . . ? C8 C7 Co1 69.80(9) . . ? C11 C7 Co1 69.47(9) . . ? C8 C7 H7A 126.0 . . ? C11 C7 H7A 126.0 . . ? Co1 C7 H7A 126.0 . . ? C7 C8 C9 108.0 . . ? C7 C8 Co1 69.49(9) . . ? C9 C8 Co1 69.62(9) . . ? C7 C8 H8A 126.0 . . ? C9 C8 H8A 126.0 . . ? Co1 C8 H8A 126.0 . . ? C10 C9 C8 108.0 . . ? C10 C9 Co1 69.45(9) . . ? C8 C9 Co1 69.70(9) . . ? C10 C9 H9A 126.0 . . ? C8 C9 H9A 126.0 . . ? Co1 C9 H9A 126.0 . . ? C11 C10 C9 108.0 . . ? C11 C10 Co1 69.52(9) . . ? C9 C10 Co1 69.81(9) . . ? C11 C10 H10A 126.0 . . ? C9 C10 H10A 126.0 . . ? Co1 C10 H10A 126.0 . . ? C10 C11 C7 108.0 . . ? C10 C11 C12 124.9(2) . . ? C7 C11 C12 127.0(2) . . ? C10 C11 Co1 69.67(9) . . ? C7 C11 Co1 69.74(9) . . ? C12 C11 Co1 123.41(19) . . ? O3 C12 O4 125.7(3) . . ? O3 C12 C11 121.4(3) . . ? O4 C12 C11 112.9(3) . . ? C12 O4 H400 108(3) . . ? O6 C13 O5 128.1(3) . . ? O6 C13 C14 118.9(3) . . ? O5 C13 C14 113.0(3) . . ? F1 C14 C13 111.3(3) . . ? F1 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? F1 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.990 _refine_diff_density_min -0.752 _refine_diff_density_rms 0.109 data_2-[H2CClCOO] _database_code_CSD 204247 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Cl Co O6' _chemical_formula_weight 370.62 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' Cl Cl 0.1484 0.1585 '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' 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(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.452(3) _cell_length_b 12.949(3) _cell_length_c 14.886(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.36(3) _cell_angle_gamma 90.00 _cell_volume 1403.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.754 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 1.440 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min 0.7813 _exptl_absorpt_correction_T_max 1.0000 _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 3160 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0113 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 26.98 _reflns_number_total 3048 _reflns_number_gt 2755 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0637P)^2^+1.0429P] 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 3048 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1085 _refine_ls_wR_factor_gt 0.1051 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 0.10078(4) 0.19655(2) 0.36247(2) 0.02999(13) Uani 1 1 d . . . C1 C -0.0482(3) 0.18106(14) 0.23149(11) 0.0430(6) Uani 1 1 d G . . H1A H 0.0018 0.1722 0.1762 0.052 Uiso 1 1 calc R . . C2 C -0.0900(3) 0.27662(11) 0.26911(14) 0.0470(6) Uani 1 1 d G . . H2A H -0.0732 0.3453 0.2446 0.056 Uiso 1 1 calc R . . C3 C -0.1583(3) 0.25519(12) 0.34918(13) 0.0470(6) Uani 1 1 d G . . H3A H -0.1969 0.3065 0.3896 0.056 Uiso 1 1 calc R . . C4 C -0.1587(3) 0.14639(12) 0.36106(12) 0.0406(6) Uani 1 1 d G . . H4A H -0.1984 0.1094 0.4109 0.049 Uiso 1 1 calc R . . C5 C -0.0907(2) 0.10057(10) 0.28832(12) 0.0366(5) Uani 1 1 d G . . C6 C -0.0568(3) -0.0111(2) 0.27584(19) 0.0419(6) Uani 1 1 d . . . O1 O -0.0059(5) -0.0422(2) 0.2092(2) 0.0807(8) Uani 1 1 d . . . O2 O -0.0868(3) -0.06750(15) 0.34289(16) 0.0511(5) Uani 1 1 d . . . C7 C 0.3723(3) 0.20019(14) 0.35768(11) 0.0412(6) Uani 1 1 d G . . H7A H 0.4223 0.1962 0.3020 0.049 Uiso 1 1 calc R . . C8 C 0.3232(3) 0.29197(10) 0.39880(13) 0.0456(6) Uani 1 1 d G . . H8A H 0.3330 0.3625 0.3764 0.055 Uiso 1 1 calc R . . C9 C 0.2554(3) 0.26359(12) 0.47750(12) 0.0448(6) Uani 1 1 d G . . H9A H 0.2104 0.3111 0.5190 0.054 Uiso 1 1 calc R . . C10 C 0.2625(3) 0.15427(12) 0.48502(11) 0.0393(5) Uani 1 1 d G . . H10A H 0.2240 0.1131 0.5328 0.047 Uiso 1 1 calc R . . C11 C 0.3348(2) 0.11510(10) 0.41097(12) 0.0359(5) Uani 1 1 d G . . C12 C 0.3610(4) 0.0049(2) 0.38979(18) 0.0419(6) Uani 1 1 d . . . O3 O 0.4269(4) -0.0201(2) 0.32577(18) 0.0774(8) Uani 1 1 d . . . O4 O 0.3096(3) -0.05754(15) 0.44788(14) 0.0493(5) Uani 1 1 d . . . C13 C 0.1619(6) -0.4129(3) 0.3972(3) 0.0557(8) Uani 1 1 d . . . C14 C 0.1509(4) -0.2953(2) 0.39093(19) 0.0407(6) Uani 1 1 d . A . O5 O 0.0030(3) -0.25688(17) 0.3533(2) 0.0649(6) Uani 1 1 d . . . O6 O 0.2971(3) -0.24911(17) 0.4216(2) 0.0677(7) Uani 1 1 d . . . Cl1 Cl -0.0478(2) -0.47473(9) 0.38255(10) 0.0602(3) Uani 0.60 1 d P A 1 H13A H 0.236(10) -0.463(6) 0.478(6) 0.072 Uiso 0.60 1 d P B 1 H13B H 0.238(10) -0.450(6) 0.366(6) 0.072 Uiso 0.60 1 d P C 1 H13A' H 0.179(18) -0.427(11) 0.368(10) 0.072 Uiso 0.40 1 d P D 2 H13B' H 0.241(13) -0.479(8) 0.520(7) 0.072 Uiso 0.40 1 d P E 2 Cl2 Cl 0.3218(5) -0.45701(17) 0.4881(2) 0.0912(11) Uani 0.40 1 d P A 2 H200 H -0.0540 -0.1278 0.3402 0.059 Uiso 1 1 d . . . H400 H 0.2903 -0.1286 0.4244 0.074 Uiso 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 0.02886(19) 0.03139(19) 0.02991(19) 0.00296(11) 0.00673(13) 0.00068(11) C1 0.0356(12) 0.0543(15) 0.0355(13) 0.0077(11) -0.0003(10) -0.0010(11) C2 0.0367(13) 0.0431(14) 0.0565(17) 0.0138(12) -0.0006(12) 0.0046(11) C3 0.0343(12) 0.0434(14) 0.0633(18) -0.0008(13) 0.0106(12) 0.0077(11) C4 0.0301(11) 0.0428(13) 0.0521(15) 0.0005(11) 0.0158(10) 0.0001(10) C5 0.0293(10) 0.0408(13) 0.0382(12) 0.0002(10) 0.0040(9) -0.0015(9) C6 0.0354(12) 0.0426(13) 0.0474(14) -0.0077(11) 0.0080(11) -0.0030(10) O1 0.124(2) 0.0577(14) 0.0722(17) -0.0134(13) 0.0476(17) 0.0078(15) O2 0.0532(11) 0.0364(9) 0.0660(13) 0.0025(9) 0.0177(10) 0.0006(8) C7 0.0291(11) 0.0549(16) 0.0392(13) 0.0050(11) 0.0063(10) -0.0014(10) C8 0.0397(13) 0.0404(13) 0.0546(16) 0.0029(11) 0.0052(12) -0.0095(11) C9 0.0478(14) 0.0441(14) 0.0399(14) -0.0090(11) 0.0033(11) -0.0024(11) C10 0.0431(13) 0.0452(14) 0.0283(11) 0.0005(10) 0.0046(10) 0.0025(11) C11 0.0303(10) 0.0444(13) 0.0307(11) 0.0030(10) 0.0017(9) 0.0045(9) C12 0.0402(12) 0.0464(14) 0.0355(12) 0.0002(11) 0.0000(10) 0.0126(11) O3 0.116(2) 0.0637(15) 0.0617(14) 0.0003(12) 0.0400(15) 0.0321(15) O4 0.0532(11) 0.0410(10) 0.0514(12) -0.0007(8) 0.0062(9) -0.0004(8) C13 0.075(2) 0.0357(14) 0.057(2) -0.0028(14) 0.0167(18) 0.0016(14) C14 0.0530(15) 0.0354(13) 0.0362(13) -0.0001(10) 0.0152(11) 0.0020(11) O5 0.0549(13) 0.0393(11) 0.0968(19) 0.0050(11) 0.0079(12) 0.0028(10) O6 0.0613(14) 0.0406(11) 0.0929(18) -0.0038(12) -0.0023(13) -0.0013(10) Cl1 0.0720(8) 0.0404(6) 0.0699(8) -0.0001(5) 0.0188(7) -0.0103(6) Cl2 0.141(3) 0.0389(10) 0.0687(15) -0.0009(10) -0.0325(17) 0.0195(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 C5 2.0307(18) . ? Co1 C11 2.0337(18) . ? Co1 C10 2.0345(19) . ? Co1 C4 2.0356(19) . ? Co1 C1 2.037(2) . ? Co1 C7 2.040(2) . ? Co1 C9 2.042(2) . ? Co1 C3 2.0445(19) . ? Co1 C2 2.0452(19) . ? Co1 C8 2.0452(19) . ? C1 C5 1.4200 . ? C1 C2 1.4200 . ? C1 H1A 0.9800 . ? C2 C3 1.4200 . ? C2 H2A 0.9800 . ? C3 C4 1.4200 . ? C3 H3A 0.9800 . ? C4 C5 1.4200 . ? C4 H4A 0.9800 . ? C5 C6 1.487(3) . ? C6 O1 1.204(4) . ? C6 O2 1.294(3) . ? O2 H200 0.8215 . ? C7 C8 1.4200 . ? C7 C11 1.4200 . ? C7 H7A 0.9800 . ? C8 C9 1.4200 . ? C8 H8A 0.9800 . ? C9 C10 1.4200 . ? C9 H9A 0.9800 . ? C10 C11 1.4200 . ? C10 H10A 0.9800 . ? C11 C12 1.483(3) . ? C12 O3 1.206(4) . ? C12 O4 1.300(4) . ? O4 H400 0.9838 . ? C13 C14 1.526(4) . ? C13 Cl2 1.700(5) . ? C13 Cl1 1.727(4) . ? C13 H13A 1.37(9) . ? C13 H13B 0.94(8) . ? C13 H13A 0.52(14) . ? C14 O5 1.229(4) . ? C14 O6 1.241(4) . ? Cl2 H13A 0.63(7) . ? Cl2 H13B 1.79(9) . ? Cl2 H13B 0.89(11) . ? 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 C5 Co1 C11 108.95(7) . . ? C5 Co1 C10 122.36(7) . . ? C11 Co1 C10 40.9 . . ? C5 Co1 C4 40.9 . . ? C11 Co1 C4 125.36(7) . . ? C10 Co1 C4 107.61(7) . . ? C5 Co1 C1 40.9 . . ? C11 Co1 C1 122.63(7) . . ? C10 Co1 C1 158.26(7) . . ? C4 Co1 C1 68.7 . . ? C5 Co1 C7 125.57(7) . . ? C11 Co1 C7 40.8 . . ? C10 Co1 C7 68.6 . . ? C4 Co1 C7 162.54(7) . . ? C1 Co1 C7 108.08(7) . . ? C5 Co1 C9 157.03(7) . . ? C11 Co1 C9 68.6 . . ? C10 Co1 C9 40.8 . . ? C4 Co1 C9 120.57(7) . . ? C1 Co1 C9 159.87(8) . . ? C7 Co1 C9 68.5 . . ? C5 Co1 C3 68.6 . . ? C11 Co1 C3 161.31(7) . . ? C10 Co1 C3 123.55(8) . . ? C4 Co1 C3 40.7 . . ? C1 Co1 C3 68.5 . . ? C7 Co1 C3 155.65(7) . . ? C9 Co1 C3 105.96(7) . . ? C5 Co1 C2 68.6 . . ? C11 Co1 C2 157.34(7) . . ? C10 Co1 C2 159.73(8) . . ? C4 Co1 C2 68.5 . . ? C1 Co1 C2 40.7 . . ? C7 Co1 C2 121.00(7) . . ? C9 Co1 C2 122.67(8) . . ? C3 Co1 C2 40.6 . . ? C5 Co1 C8 161.57(7) . . ? C11 Co1 C8 68.6 . . ? C10 Co1 C8 68.6 . . ? C4 Co1 C8 155.48(7) . . ? C1 Co1 C8 123.89(7) . . ? C7 Co1 C8 40.7 . . ? C9 Co1 C8 40.7 . . ? C3 Co1 C8 119.76(7) . . ? C2 Co1 C8 106.24(7) . . ? C5 C1 C2 108.0 . . ? C5 C1 Co1 69.34(7) . . ? C2 C1 Co1 69.96(7) . . ? C5 C1 H1A 126.0 . . ? C2 C1 H1A 126.0 . . ? Co1 C1 H1A 126.0 . . ? C3 C2 C1 108.0 . . ? C3 C2 Co1 69.66(7) . . ? C1 C2 Co1 69.32(7) . . ? C3 C2 H2A 126.0 . . ? C1 C2 H2A 126.0 . . ? Co1 C2 H2A 126.0 . . ? C2 C3 C4 108.0 . . ? C2 C3 Co1 69.71(7) . . ? C4 C3 Co1 69.30(6) . . ? C2 C3 H3A 126.0 . . ? C4 C3 H3A 126.0 . . ? Co1 C3 H3A 126.0 . . ? C3 C4 C5 108.0 . . ? C3 C4 Co1 69.97(7) . . ? C5 C4 Co1 69.38(7) . . ? C3 C4 H4A 126.0 . . ? C5 C4 H4A 126.0 . . ? Co1 C4 H4A 126.0 . . ? C4 C5 C1 108.0 . . ? C4 C5 C6 126.85(16) . . ? C1 C5 C6 125.04(16) . . ? C4 C5 Co1 69.75(7) . . ? C1 C5 Co1 69.79(7) . . ? C6 C5 Co1 123.02(15) . . ? O1 C6 O2 125.7(3) . . ? O1 C6 C5 121.3(3) . . ? O2 C6 C5 113.0(2) . . ? C6 O2 H200 113.4 . . ? C8 C7 C11 108.0 . . ? C8 C7 Co1 69.85(7) . . ? C11 C7 Co1 69.35(7) . . ? C8 C7 H7A 126.0 . . ? C11 C7 H7A 126.0 . . ? Co1 C7 H7A 126.0 . . ? C9 C8 C7 108.0 . . ? C9 C8 Co1 69.53(7) . . ? C7 C8 Co1 69.48(7) . . ? C9 C8 H8A 126.0 . . ? C7 C8 H8A 126.0 . . ? Co1 C8 H8A 126.0 . . ? C8 C9 C10 108.0 . . ? C8 C9 Co1 69.81(7) . . ? C10 C9 Co1 69.34(7) . . ? C8 C9 H9A 126.0 . . ? C10 C9 H9A 126.0 . . ? Co1 C9 H9A 126.0 . . ? C9 C10 C11 108.0 . . ? C9 C10 Co1 69.88(7) . . ? C11 C10 Co1 69.54(7) . . ? C9 C10 H10A 126.0 . . ? C11 C10 H10A 126.0 . . ? Co1 C10 H10A 126.0 . . ? C10 C11 C7 108.0 . . ? C10 C11 C12 126.71(16) . . ? C7 C11 C12 125.25(16) . . ? C10 C11 Co1 69.60(7) . . ? C7 C11 Co1 69.85(7) . . ? C12 C11 Co1 124.44(15) . . ? O3 C12 O4 125.9(3) . . ? O3 C12 C11 121.4(3) . . ? O4 C12 C11 112.7(2) . . ? C12 O4 H400 112.8 . . ? C14 C13 Cl2 113.8(3) . . ? C14 C13 Cl1 114.8(3) . . ? Cl2 C13 Cl1 113.9(3) . . ? C14 C13 H13A 122(3) . . ? Cl2 C13 H13A 20(3) . . ? Cl1 C13 H13A 94(3) . . ? C14 C13 H13B 121(5) . . ? Cl2 C13 H13B 80(5) . . ? Cl1 C13 H13B 109(5) . . ? H13A C13 H13B 90(5) . . ? C14 C13 H13A 108(10) . . ? Cl2 C13 H13A 107(10) . . ? Cl1 C13 H13A 97(10) . . ? H13A C13 H13A 117(10) . . ? H13B C13 H13A 28(10) . . ? O5 C14 O6 127.1(3) . . ? O5 C14 C13 117.6(3) . . ? O6 C14 C13 115.3(3) . . ? C13 Cl2 H13A 49(8) . . ? C13 Cl2 H13B 31(2) . . ? H13A Cl2 H13B 69(8) . . ? C13 Cl2 H13B 95(6) . . ? H13A Cl2 H13B 47(9) . . ? H13B Cl2 H13B 115(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.092 _refine_diff_density_min -0.602 _refine_diff_density_rms 0.076