Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'M. Hardie' _publ_contact_author_address ; School of Chemistry University of Leeds Woodhouse Lane Leeds LS2 9JT UNITED KINGDOM ; _publ_contact_author_email M.J.HARDIE@LEEDS.AC.UK _publ_section_title ; Coordination and hydrogen bonded network structures of Cu(II) with mixed ligands: a hybrid hydrogen bonded material, an infinite sandwich arrangement, and a 3-D net. ; loop_ _publ_author_name 'M. Hardie' 'Maria D. Stephenson' # Attachment 'allcomplexes_revised.cif' data_complex_1 _database_code_depnum_ccdc_archive 'CCDC 265315' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tetrachlorobis(1,10-phenanthroline-5,6-dione)dicopper(II) acetonitrile clathrate ; _chemical_name_common ;tetrachlorobis(1,10-phenanthroline-5,6-dione)dicopper(ii) acetonitrile clathrate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H9 Cl2 Cu N3 O2' _chemical_formula_weight 385.68 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' Cl Cl 0.1484 0.1585 '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 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 8.3147(1) _cell_length_b 13.5527(2) _cell_length_c 13.4095(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.696(1) _cell_angle_gamma 90.00 _cell_volume 1468.10(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.745 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 1.860 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.4626 _exptl_absorpt_correction_T_max 0.9127 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _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 21813 _diffrn_reflns_av_R_equivalents 0.0849 _diffrn_reflns_av_sigmaI/netI 0.0569 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3362 _reflns_number_gt 2571 _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^)+(0.0549P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3362 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0866 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 Cu1 Cu 0.18975(3) 0.49194(2) 0.97903(2) 0.02116(12) Uani 1 1 d . . . Cl1 Cl -0.00472(7) 0.60817(4) 0.91818(5) 0.02603(16) Uani 1 1 d . . . O1 O 0.8200(2) 0.36785(13) 1.34073(14) 0.0352(5) Uani 1 1 d . . . N1 N 0.3794(2) 0.39998(14) 1.04217(15) 0.0217(4) Uani 1 1 d . . . Cl2 Cl 0.13755(7) 0.41284(5) 0.82801(4) 0.02817(17) Uani 1 1 d . . . O2 O 0.7505(2) 0.55422(14) 1.39902(13) 0.0319(4) Uani 1 1 d . . . C2 C 0.4078(3) 0.31036(18) 1.0079(2) 0.0281(6) Uani 1 1 d . . . H2 H 0.3402 0.2878 0.9447 0.034 Uiso 1 1 calc R . . C3 C 0.5323(3) 0.24950(19) 1.0616(2) 0.0301(6) Uani 1 1 d . . . H3 H 0.5495 0.1862 1.0356 0.036 Uiso 1 1 calc R . . C4 C 0.6312(3) 0.28203(18) 1.15362(19) 0.0281(6) Uani 1 1 d . . . H4 H 0.7172 0.2413 1.1916 0.034 Uiso 1 1 calc R . . C5 C 0.7067(3) 0.41422(19) 1.28810(19) 0.0269(6) Uani 1 1 d . . . C6 C 0.6655(3) 0.51786(19) 1.3224(2) 0.0258(6) Uani 1 1 d . . . C7 C 0.4634(3) 0.65905(19) 1.2898(2) 0.0294(6) Uani 1 1 d . . . H7 H 0.5190 0.6885 1.3528 0.035 Uiso 1 1 calc R . . C8 C 0.3277(3) 0.70461(19) 1.2276(2) 0.0313(6) Uani 1 1 d . . . H8 H 0.2890 0.7659 1.2471 0.038 Uiso 1 1 calc R . . C9 C 0.2484(3) 0.65939(18) 1.1358(2) 0.0275(6) Uani 1 1 d . . . H9 H 0.1556 0.6913 1.0930 0.033 Uiso 1 1 calc R . . N10 N 0.2978(2) 0.57298(14) 1.10593(15) 0.0225(4) Uani 1 1 d . . . C11 C 0.4310(3) 0.52860(17) 1.16714(19) 0.0213(5) Uani 1 1 d . . . C12 C 0.4745(3) 0.43204(17) 1.13214(18) 0.0216(5) Uani 1 1 d . . . C13 C 0.5176(3) 0.56966(18) 1.25901(18) 0.0233(5) Uani 1 1 d . . . C14 C 0.6034(3) 0.37499(18) 1.18978(19) 0.0234(5) Uani 1 1 d . . . N20 N 0.4361(4) 0.3857(2) 1.4039(3) 0.0583(8) Uani 1 1 d . . . C21 C 0.3232(4) 0.4349(3) 1.3939(2) 0.0449(8) Uani 1 1 d . . . C22 C 0.1799(4) 0.4993(3) 1.3774(3) 0.0664(13) Uani 1 1 d . . . H22C H 0.2110 0.5617 1.4137 0.104(19) Uiso 1 1 calc R . . H22A H 0.0924 0.4675 1.4036 0.085(13) Uiso 1 1 calc R . . H22B H 0.1396 0.5121 1.3038 0.077(13) Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02016(18) 0.02095(18) 0.02122(18) 0.00007(11) 0.00262(13) 0.00164(11) Cl1 0.0248(3) 0.0233(3) 0.0292(3) 0.0067(2) 0.0048(3) 0.0034(2) O1 0.0318(10) 0.0324(10) 0.0354(11) 0.0075(8) -0.0040(8) 0.0021(9) N1 0.0221(10) 0.0220(11) 0.0205(10) -0.0005(8) 0.0040(8) -0.0008(9) Cl2 0.0280(3) 0.0334(4) 0.0218(3) -0.0029(2) 0.0034(3) 0.0016(3) O2 0.0325(10) 0.0386(11) 0.0219(9) -0.0019(8) 0.0011(8) -0.0086(9) C2 0.0276(13) 0.0269(14) 0.0280(14) -0.0049(11) 0.0032(11) 0.0015(11) C3 0.0344(14) 0.0202(13) 0.0350(15) -0.0021(11) 0.0070(12) 0.0060(11) C4 0.0279(13) 0.0229(13) 0.0319(14) 0.0048(11) 0.0038(11) 0.0043(11) C5 0.0243(12) 0.0284(14) 0.0265(13) 0.0046(11) 0.0032(11) -0.0023(11) C6 0.0246(13) 0.0296(14) 0.0238(14) 0.0035(11) 0.0070(11) -0.0069(11) C7 0.0293(13) 0.0275(14) 0.0309(14) -0.0076(11) 0.0064(11) -0.0058(11) C8 0.0341(14) 0.0213(13) 0.0379(15) -0.0062(11) 0.0073(12) 0.0011(11) C9 0.0266(13) 0.0208(12) 0.0345(15) -0.0009(11) 0.0057(11) 0.0004(11) N10 0.0222(10) 0.0191(10) 0.0251(11) 0.0011(8) 0.0035(8) 0.0008(8) C11 0.0215(12) 0.0200(12) 0.0238(13) 0.0004(10) 0.0079(10) -0.0013(10) C12 0.0196(11) 0.0212(12) 0.0250(13) 0.0007(10) 0.0076(10) -0.0014(10) C13 0.0247(12) 0.0229(13) 0.0228(12) 0.0002(10) 0.0066(10) -0.0047(10) C14 0.0210(12) 0.0242(13) 0.0245(13) 0.0034(10) 0.0046(10) -0.0006(10) N20 0.0643(19) 0.0443(17) 0.075(2) -0.0065(16) 0.0344(17) -0.0136(16) C21 0.0481(19) 0.056(2) 0.0300(16) 0.0022(15) 0.0076(14) -0.0234(18) C22 0.0370(19) 0.109(4) 0.051(2) 0.045(2) 0.0045(16) 0.0018(19) _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 N1 2.031(2) . ? Cu1 N10 2.046(2) . ? Cu1 Cl2 2.2411(6) . ? Cu1 Cl1 2.2665(6) . ? Cu1 Cl1 2.6668(7) 3_567 ? Cl1 Cu1 2.6668(7) 3_567 ? O1 C5 1.211(3) . ? N1 C2 1.339(3) . ? N1 C12 1.348(3) . ? O2 C6 1.206(3) . ? C2 C3 1.385(3) . ? C3 C4 1.383(3) . ? C4 C14 1.389(3) . ? C5 C14 1.491(3) . ? C5 C6 1.542(4) . ? C6 C13 1.494(4) . ? C7 C8 1.380(4) . ? C7 C13 1.389(3) . ? C8 C9 1.393(4) . ? C9 N10 1.334(3) . ? N10 C11 1.353(3) . ? C11 C13 1.388(3) . ? C11 C12 1.464(3) . ? C12 C14 1.397(3) . ? N20 C21 1.133(4) . ? C21 C22 1.451(5) . ? 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 N1 Cu1 N10 80.68(8) . . ? N1 Cu1 Cl2 92.77(6) . . ? N10 Cu1 Cl2 164.03(6) . . ? N1 Cu1 Cl1 173.68(6) . . ? N10 Cu1 Cl1 93.53(6) . . ? Cl2 Cu1 Cl1 92.18(2) . . ? N1 Cu1 Cl1 87.62(6) . 3_567 ? N10 Cu1 Cl1 92.10(6) . 3_567 ? Cl2 Cu1 Cl1 102.22(2) . 3_567 ? Cl1 Cu1 Cl1 95.16(2) . 3_567 ? Cu1 Cl1 Cu1 84.84(2) . 3_567 ? C2 N1 C12 119.1(2) . . ? C2 N1 Cu1 126.58(17) . . ? C12 N1 Cu1 114.10(15) . . ? N1 C2 C3 122.2(2) . . ? C4 C3 C2 119.2(2) . . ? C3 C4 C14 119.2(2) . . ? O1 C5 C14 122.4(2) . . ? O1 C5 C6 119.8(2) . . ? C14 C5 C6 117.8(2) . . ? O2 C6 C13 122.0(2) . . ? O2 C6 C5 120.0(2) . . ? C13 C6 C5 118.0(2) . . ? C8 C7 C13 119.1(2) . . ? C7 C8 C9 119.0(2) . . ? N10 C9 C8 122.5(2) . . ? C9 N10 C11 118.3(2) . . ? C9 N10 Cu1 128.00(17) . . ? C11 N10 Cu1 113.64(16) . . ? N10 C11 C13 122.6(2) . . ? N10 C11 C12 115.6(2) . . ? C13 C11 C12 121.8(2) . . ? N1 C12 C14 121.8(2) . . ? N1 C12 C11 116.0(2) . . ? C14 C12 C11 122.2(2) . . ? C11 C13 C7 118.5(2) . . ? C11 C13 C6 120.0(2) . . ? C7 C13 C6 121.5(2) . . ? C4 C14 C12 118.6(2) . . ? C4 C14 C5 121.6(2) . . ? C12 C14 C5 119.9(2) . . ? N20 C21 C22 177.8(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.469 _refine_diff_density_min -0.690 _refine_diff_density_rms 0.143 #===END data_complex_2 _database_code_depnum_ccdc_archive 'CCDC 265316' _audit_creation_method SHELXL-97 _chemical_name_systematic ; nitrobis(1,10-phenanthroline-5,6-dione)copper(II) nitrate acetonitrile clathrate ; _chemical_name_common ;nitrobis(1,10-phenanthroline-5,6-dione)copper(ii) nitrate acetonitrile clathrate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H15 Cu N7 O10' _chemical_formula_weight 648.99 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 Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 15.158(3) _cell_length_b 12.213(2) _cell_length_c 14.874(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2753.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1316 _exptl_absorpt_coefficient_mu 0.864 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.8670 _exptl_absorpt_correction_T_max 0.8705 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 _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 11667 _diffrn_reflns_av_R_equivalents 0.0936 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 22.50 _reflns_number_total 1796 _reflns_number_gt 1533 _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^)+(0.1363P)^2^+7.0456P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1796 _refine_ls_number_parameters 227 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0878 _refine_ls_R_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.2383 _refine_ls_wR_factor_gt 0.2260 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.168 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.79176(9) 0.2500 0.0435(6) Uani 1 2 d S . . O3 O 0.4219(14) 1.4899(9) 0.4985(7) 0.200(7) Uani 1 1 d . . . O5 O 0.7394(4) 0.6718(5) -0.0948(4) 0.0754(16) Uani 1 1 d . . . O6 O 0.8073(3) 0.5359(4) 0.0332(4) 0.0719(16) Uani 1 1 d . . . O21 O 0.5654(4) 0.9574(8) 0.2702(5) 0.109(3) Uani 1 1 d . . . O22 O 0.4639(8) 1.1098(8) 0.2524(7) 0.067(4) Uani 0.50 1 d P . . O31 O 0.4963(9) 1.5093(18) 0.3979(17) 0.131(7) Uani 0.50 1 d P . . N1 N 0.5261(4) 0.7944(4) 0.1184(4) 0.0462(14) Uani 1 1 d . . . N10 N 0.6108(4) 0.6910(5) 0.2491(3) 0.0477(15) Uani 1 1 d . . . N20 N 0.5000 1.0135(7) 0.2500 0.062(3) Uani 1 2 d S . . N30 N 0.4799(11) 1.5051(18) 0.4627(15) 0.083(6) Uani 0.50 1 d P . . N40 N 0.3186(6) 1.3107(7) 0.4091(6) 0.0244(19) Uani 0.50 1 d PD . . C2 C 0.4802(5) 0.8483(6) 0.0561(5) 0.0516(18) Uani 1 1 d . . . H2 H 0.4276 0.8852 0.0730 0.062 Uiso 1 1 calc R . . C3 C 0.5074(5) 0.8518(6) -0.0330(5) 0.057(2) Uani 1 1 d . . . H3 H 0.4746 0.8925 -0.0759 0.069 Uiso 1 1 calc R . . C4 C 0.5815(5) 0.7963(6) -0.0586(5) 0.0558(19) Uani 1 1 d . . . H4 H 0.6007 0.7980 -0.1194 0.067 Uiso 1 1 calc R . . C5 C 0.7071(5) 0.6711(6) -0.0186(5) 0.0596(19) Uani 1 1 d . . . C6 C 0.7483(5) 0.5978(6) 0.0527(5) 0.0588(19) Uani 1 1 d . . . C7 C 0.7518(5) 0.5512(6) 0.2181(6) 0.061(2) Uani 1 1 d . . . H7 H 0.7991 0.5017 0.2078 0.073 Uiso 1 1 calc R . . C8 C 0.7205(5) 0.5662(6) 0.3030(6) 0.063(2) Uani 1 1 d . . . H8 H 0.7466 0.5287 0.3523 0.076 Uiso 1 1 calc R . . C9 C 0.6499(5) 0.6373(6) 0.3168(5) 0.0575(19) Uani 1 1 d . . . H9 H 0.6287 0.6481 0.3762 0.069 Uiso 1 1 calc R . . C11 C 0.5989(4) 0.7380(5) 0.0933(4) 0.0467(16) Uani 1 1 d . . . C12 C 0.6433(4) 0.6776(5) 0.1654(4) 0.0464(16) Uani 1 1 d . . . C13 C 0.6285(5) 0.7371(6) 0.0055(5) 0.0508(17) Uani 1 1 d . . . C14 C 0.7148(4) 0.6078(5) 0.1464(5) 0.0502(17) Uani 1 1 d . . . C41 C 0.3623(10) 1.3260(13) 0.3473(15) 0.108(9) Uani 0.50 1 d PD . . C42 C 0.4363(14) 1.3749(16) 0.3031(14) 0.108(8) Uani 0.50 1 d PD . . H42A H 0.4363 1.3537 0.2396 0.162 Uiso 0.50 1 calc PR . . H42B H 0.4909 1.3498 0.3316 0.162 Uiso 0.50 1 calc PR . . H42C H 0.4322 1.4548 0.3079 0.162 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 Cu1 0.0422(8) 0.0501(8) 0.0383(8) 0.000 -0.0009(4) 0.000 O3 0.39(2) 0.123(8) 0.086(8) 0.014(6) -0.010(11) 0.037(12) O5 0.082(4) 0.074(4) 0.070(4) 0.001(3) 0.028(3) 0.009(3) O6 0.060(3) 0.058(3) 0.097(4) -0.002(3) 0.024(3) 0.010(3) O21 0.043(3) 0.204(9) 0.079(4) 0.063(5) 0.000(3) -0.004(5) O22 0.106(10) 0.048(6) 0.048(6) 0.002(5) -0.010(8) -0.005(5) O31 0.069(9) 0.172(17) 0.151(19) 0.082(15) 0.036(10) -0.015(9) N1 0.045(3) 0.055(3) 0.038(3) -0.003(2) 0.000(3) 0.008(3) N10 0.047(3) 0.048(3) 0.048(4) 0.006(3) -0.003(2) 0.000(3) N20 0.098(8) 0.045(6) 0.042(5) 0.000 -0.005(5) 0.000 N30 0.054(9) 0.149(16) 0.047(9) 0.011(10) 0.008(7) -0.052(10) N40 0.020(4) 0.016(4) 0.037(5) -0.001(4) 0.007(4) -0.008(4) C2 0.056(4) 0.057(4) 0.041(4) -0.002(3) -0.007(3) 0.012(3) C3 0.071(5) 0.057(5) 0.044(4) 0.005(3) -0.008(3) 0.004(4) C4 0.064(5) 0.059(4) 0.044(4) 0.004(3) 0.006(3) 0.004(4) C5 0.064(5) 0.053(4) 0.062(5) -0.003(4) 0.014(4) -0.001(4) C6 0.046(4) 0.049(4) 0.081(5) 0.000(4) 0.009(4) 0.001(3) C7 0.051(4) 0.051(4) 0.081(6) 0.011(4) -0.002(4) 0.006(3) C8 0.057(4) 0.064(5) 0.068(5) 0.015(4) -0.015(4) 0.005(4) C9 0.062(4) 0.057(4) 0.053(4) 0.017(4) -0.003(4) -0.010(4) C11 0.050(4) 0.047(4) 0.043(4) -0.001(3) -0.002(3) 0.003(3) C12 0.040(4) 0.051(4) 0.049(4) 0.007(3) 0.000(3) 0.000(3) C13 0.058(4) 0.050(4) 0.045(4) -0.001(3) 0.009(3) -0.002(3) C14 0.044(4) 0.040(3) 0.066(5) 0.004(3) 0.005(3) 0.001(3) C41 0.047(10) 0.049(10) 0.23(3) 0.078(14) -0.002(14) 0.022(8) C42 0.15(2) 0.091(14) 0.079(14) -0.021(11) -0.009(13) 0.047(15) _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 N1 1.997(6) 4_655 ? Cu1 N1 1.997(6) . ? Cu1 N10 2.082(6) 4_655 ? Cu1 N10 2.082(6) . ? Cu1 O21 2.273(9) . ? Cu1 O21 2.273(9) 4_655 ? O3 N30 1.04(2) . ? O3 N30 1.60(2) 5_686 ? O5 C5 1.234(9) . ? O6 C6 1.208(8) . ? O21 N20 1.242(8) . ? O22 O22 1.10(2) 4_655 ? O22 N20 1.298(13) . ? O31 N30 1.00(2) . ? N1 C2 1.333(9) . ? N1 C11 1.353(9) . ? N10 C9 1.340(8) . ? N10 C12 1.348(8) . ? N20 O21 1.242(8) 4_655 ? N20 O22 1.298(13) 4_655 ? N30 N30 1.27(4) 5_686 ? N30 O3 1.60(2) 5_686 ? N40 C41 1.148(16) . ? C2 C3 1.388(11) . ? C3 C4 1.366(11) . ? C4 C13 1.393(10) . ? C5 C13 1.483(10) . ? C5 C6 1.522(11) . ? C6 C14 1.488(10) . ? C7 C8 1.362(12) . ? C7 C14 1.390(10) . ? C8 C9 1.394(11) . ? C11 C13 1.381(10) . ? C11 C12 1.465(9) . ? C12 C14 1.408(9) . ? C41 C42 1.431(17) . ? 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 N1 Cu1 N1 178.2(3) 4_655 . ? N1 Cu1 N10 81.0(2) 4_655 4_655 ? N1 Cu1 N10 100.1(2) . 4_655 ? N1 Cu1 N10 100.1(2) 4_655 . ? N1 Cu1 N10 81.0(2) . . ? N10 Cu1 N10 107.6(3) 4_655 . ? N1 Cu1 O21 86.7(2) 4_655 . ? N1 Cu1 O21 91.7(2) . . ? N10 Cu1 O21 151.3(3) 4_655 . ? N10 Cu1 O21 100.1(2) . . ? N1 Cu1 O21 91.7(2) 4_655 4_655 ? N1 Cu1 O21 86.7(2) . 4_655 ? N10 Cu1 O21 100.1(2) 4_655 4_655 ? N10 Cu1 O21 151.3(3) . 4_655 ? O21 Cu1 O21 54.3(3) . 4_655 ? N30 O3 N30 53(2) . 5_686 ? N20 O21 Cu1 96.3(5) . . ? O22 O22 N20 65.0(5) 4_655 . ? C2 N1 C11 119.0(6) . . ? C2 N1 Cu1 125.9(5) . . ? C11 N1 Cu1 115.1(4) . . ? C9 N10 C12 118.2(6) . . ? C9 N10 Cu1 129.8(5) . . ? C12 N10 Cu1 111.9(4) . . ? O21 N20 O21 113.1(11) 4_655 . ? O21 N20 O22 146.1(8) 4_655 4_655 ? O21 N20 O22 99.7(7) . 4_655 ? O21 N20 O22 99.7(7) 4_655 . ? O21 N20 O22 146.1(8) . . ? O22 N20 O22 50.1(10) 4_655 . ? O31 N30 O3 135(2) . . ? O31 N30 N30 137(3) . 5_686 ? O3 N30 N30 87(2) . 5_686 ? O31 N30 O3 96.6(18) . 5_686 ? O3 N30 O3 127(2) . 5_686 ? N30 N30 O3 40.7(10) 5_686 5_686 ? N1 C2 C3 121.6(7) . . ? C4 C3 C2 119.7(7) . . ? C3 C4 C13 119.1(7) . . ? O5 C5 C13 122.5(7) . . ? O5 C5 C6 118.8(7) . . ? C13 C5 C6 118.7(6) . . ? O6 C6 C14 122.0(7) . . ? O6 C6 C5 120.3(7) . . ? C14 C6 C5 117.7(6) . . ? C8 C7 C14 120.3(7) . . ? C7 C8 C9 119.2(7) . . ? N10 C9 C8 122.3(7) . . ? N1 C11 C13 122.0(6) . . ? N1 C11 C12 115.4(6) . . ? C13 C11 C12 122.6(6) . . ? N10 C12 C14 122.7(6) . . ? N10 C12 C11 116.5(6) . . ? C14 C12 C11 120.8(6) . . ? C11 C13 C4 118.6(6) . . ? C11 C13 C5 119.6(6) . . ? C4 C13 C5 121.8(6) . . ? C7 C14 C12 117.3(7) . . ? C7 C14 C6 122.7(6) . . ? C12 C14 C6 120.0(6) . . ? N40 C41 C42 153(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.160 _refine_diff_density_min -0.798 _refine_diff_density_rms 0.197 #===END data_complex_3 _database_code_depnum_ccdc_archive 'CCDC 265317' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bromobis(1,10-phenanthroline-5,6-dione)copper(II) bromide ethanol clathrate ; _chemical_name_common ;bromobis(1,10-phenanthroline-5,6-dione)copper(ii) bromide ethanol clathrate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H20 Br2 Cu N4 O6' _chemical_formula_weight 707.82 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 14.4198(4) _cell_length_b 12.2319(3) _cell_length_c 14.9169(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2631.07(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.787 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1404 _exptl_absorpt_coefficient_mu 3.917 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 _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 15900 _diffrn_reflns_av_R_equivalents 0.0745 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3000 _reflns_number_gt 1974 _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^)+(0.1000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3000 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0888 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1693 _refine_ls_wR_factor_gt 0.1480 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.008 _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 Br1 Br 0.0000 0.50759(5) 0.2500 0.0328(2) Uani 1 2 d S . . Br2 Br 0.02956(9) -0.01486(10) 0.00257(9) 0.0555(4) Uani 0.50 1 d P . . Cu1 Cu 0.0000 0.30883(6) 0.2500 0.0280(2) Uani 1 2 d S . . O15 O 0.2378(2) 0.1650(3) -0.0952(2) 0.0487(9) Uani 1 1 d . . . O16 O 0.3028(2) 0.0221(3) 0.0307(3) 0.0493(9) Uani 1 1 d . . . O20 O 0.3311(4) 0.3109(4) 0.0892(3) 0.0859(14) Uani 1 1 d . . . H20 H 0.3577 0.3516 0.0519 0.103 Uiso 1 1 calc R . . N1 N 0.0246(2) 0.3038(3) 0.1194(2) 0.0288(8) Uani 1 1 d . . . N10 N 0.1135(2) 0.1987(3) 0.2487(2) 0.0300(8) Uani 1 1 d . . . C2 C -0.0218(3) 0.3604(4) 0.0574(3) 0.0316(9) Uani 1 1 d . . . H2 H -0.0742 0.4022 0.0752 0.038 Uiso 1 1 calc R . . C3 C 0.0041(3) 0.3602(4) -0.0320(3) 0.0342(10) Uani 1 1 d . . . H3 H -0.0302 0.4012 -0.0747 0.041 Uiso 1 1 calc R . . C4 C 0.0799(3) 0.3000(3) -0.0582(3) 0.0359(10) Uani 1 1 d . . . H4 H 0.0996 0.3008 -0.1190 0.043 Uiso 1 1 calc R . . C5 C 0.2057(3) 0.1660(4) -0.0206(3) 0.0375(10) Uani 1 1 d . . . C6 C 0.2453(3) 0.0898(4) 0.0521(3) 0.0384(11) Uani 1 1 d . . . C7 C 0.2532(3) 0.0483(4) 0.2172(3) 0.0399(11) Uani 1 1 d . . . H7 H 0.3007 -0.0039 0.2065 0.048 Uiso 1 1 calc R . . C8 C 0.2232(3) 0.0683(4) 0.3031(3) 0.0408(11) Uani 1 1 d . . . H8 H 0.2502 0.0312 0.3526 0.049 Uiso 1 1 calc R . . C9 C 0.1527(3) 0.1438(4) 0.3160(3) 0.0368(10) Uani 1 1 d . . . H9 H 0.1315 0.1569 0.3753 0.044 Uiso 1 1 calc R . . C11 C 0.0976(3) 0.2423(3) 0.0937(3) 0.0286(9) Uani 1 1 d . . . C12 C 0.1434(3) 0.1800(3) 0.1647(3) 0.0302(9) Uani 1 1 d . . . C13 C 0.1272(3) 0.2384(3) 0.0047(3) 0.0315(9) Uani 1 1 d . . . C14 C 0.2135(3) 0.1052(3) 0.1460(3) 0.0348(10) Uani 1 1 d . . . C21 C 0.3776(7) 0.3183(7) 0.1741(6) 0.131(4) Uani 1 1 d . . . H21A H 0.4277 0.3722 0.1701 0.197 Uiso 1 1 calc R . . H21B H 0.4036 0.2468 0.1899 0.197 Uiso 1 1 calc R . . H21C H 0.3333 0.3410 0.2203 0.197 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0445(4) 0.0334(4) 0.0204(3) 0.000 0.0017(2) 0.000 Br2 0.0830(11) 0.0372(7) 0.0462(6) -0.0020(5) -0.0062(8) -0.0116(7) Cu1 0.0335(4) 0.0333(5) 0.0173(4) 0.000 -0.0002(3) 0.000 O15 0.061(2) 0.052(2) 0.0337(18) -0.0035(16) 0.0224(16) 0.0017(16) O16 0.050(2) 0.0407(19) 0.057(2) -0.0014(17) 0.0203(17) 0.0063(15) O20 0.101(4) 0.068(3) 0.088(4) 0.004(3) 0.022(3) 0.021(2) N1 0.0336(17) 0.034(2) 0.0191(17) 0.0020(14) -0.0015(14) 0.0005(14) N10 0.0308(18) 0.032(2) 0.0273(18) 0.0001(15) -0.0022(14) -0.0001(14) C2 0.033(2) 0.036(2) 0.026(2) 0.0011(19) -0.0036(17) 0.0008(18) C3 0.041(2) 0.037(3) 0.024(2) 0.0017(19) -0.0040(18) -0.0026(19) C4 0.049(3) 0.038(2) 0.021(2) -0.0025(18) 0.0037(19) -0.009(2) C5 0.041(3) 0.032(2) 0.040(3) -0.004(2) 0.014(2) -0.0024(19) C6 0.037(3) 0.034(2) 0.044(3) -0.003(2) 0.013(2) -0.0009(18) C7 0.034(2) 0.034(3) 0.052(3) 0.008(2) 0.001(2) 0.0007(19) C8 0.041(3) 0.040(3) 0.041(3) 0.011(2) -0.007(2) 0.001(2) C9 0.041(2) 0.040(3) 0.030(2) 0.005(2) -0.0036(19) -0.0056(19) C11 0.032(2) 0.029(2) 0.024(2) -0.0030(16) 0.0014(17) -0.0012(17) C12 0.032(2) 0.032(2) 0.027(2) -0.0012(17) -0.0025(17) -0.0025(17) C13 0.041(2) 0.029(2) 0.025(2) -0.0024(17) 0.0029(17) -0.0041(18) C14 0.035(2) 0.033(2) 0.037(2) 0.0037(19) 0.010(2) 0.0016(17) C21 0.143(8) 0.118(8) 0.133(8) -0.043(6) 0.027(7) 0.058(6) _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 Br1 Cu1 2.4312(9) . ? Br2 Br2 0.930(2) 5 ? Cu1 N1 1.981(3) 4 ? Cu1 N1 1.981(3) . ? Cu1 N10 2.119(4) 4 ? Cu1 N10 2.119(4) . ? O15 C5 1.206(5) . ? O16 C6 1.215(5) . ? O20 C21 1.437(10) . ? N1 C2 1.336(5) . ? N1 C11 1.349(5) . ? N10 C9 1.335(5) . ? N10 C12 1.345(5) . ? C2 C3 1.385(6) . ? C3 C4 1.374(6) . ? C4 C13 1.384(6) . ? C5 C13 1.485(6) . ? C5 C6 1.540(6) . ? C6 C14 1.487(6) . ? C7 C8 1.374(7) . ? C7 C14 1.392(6) . ? C8 C9 1.386(6) . ? C11 C13 1.395(5) . ? C11 C12 1.463(6) . ? C12 C14 1.392(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 N1 Cu1 N1 176.4(2) 4 . ? N1 Cu1 N10 80.39(13) 4 4 ? N1 Cu1 N10 97.33(13) . 4 ? N1 Cu1 N10 97.33(13) 4 . ? N1 Cu1 N10 80.39(13) . . ? N10 Cu1 N10 101.07(19) 4 . ? N1 Cu1 Br1 91.78(10) 4 . ? N1 Cu1 Br1 91.78(10) . . ? N10 Cu1 Br1 129.46(10) 4 . ? N10 Cu1 Br1 129.46(10) . . ? C2 N1 C11 118.9(4) . . ? C2 N1 Cu1 125.1(3) . . ? C11 N1 Cu1 115.9(3) . . ? C9 N10 C12 118.6(4) . . ? C9 N10 Cu1 129.9(3) . . ? C12 N10 Cu1 111.4(3) . . ? N1 C2 C3 122.0(4) . . ? C4 C3 C2 119.4(4) . . ? C3 C4 C13 119.4(4) . . ? O15 C5 C13 122.2(4) . . ? O15 C5 C6 120.1(4) . . ? C13 C5 C6 117.7(4) . . ? O16 C6 C14 123.0(4) . . ? O16 C6 C5 118.8(4) . . ? C14 C6 C5 118.2(4) . . ? C8 C7 C14 119.6(4) . . ? C7 C8 C9 118.6(4) . . ? N10 C9 C8 122.8(4) . . ? N1 C11 C13 121.9(4) . . ? N1 C11 C12 115.9(3) . . ? C13 C11 C12 122.2(4) . . ? N10 C12 C14 122.2(4) . . ? N10 C12 C11 116.1(4) . . ? C14 C12 C11 121.7(4) . . ? C4 C13 C11 118.4(4) . . ? C4 C13 C5 121.9(4) . . ? C11 C13 C5 119.7(4) . . ? C7 C14 C12 118.3(4) . . ? C7 C14 C6 122.0(4) . . ? C12 C14 C6 119.7(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.444 _refine_diff_density_min -1.361 _refine_diff_density_rms 0.181 #===END data_complex_4 _database_code_depnum_ccdc_archive 'CCDC 265318' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dibromobis(1,10-phenanthroline-5,6-dione)copper(II) ; _chemical_name_common dibromobis(1,10-phenanthroline-5,6-dione)copper(ii) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H12 Br2 Cu N4 O4' _chemical_formula_weight 643.74 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+1/4, -y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+1/4, -y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+3/4, -y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' _cell_length_a 41.330(5) _cell_length_b 8.3836(19) _cell_length_c 12.939(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4483.4(15) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow-brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.907 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2520 _exptl_absorpt_coefficient_mu 4.581 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.3403 _exptl_absorpt_correction_T_max 0.9730 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _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 2305 _diffrn_reflns_av_R_equivalents 0.0687 _diffrn_reflns_av_sigmaI/netI 0.1033 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 20.06 _reflns_number_total 894 _reflns_number_gt 641 _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^)+(0.1530P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(6) _refine_ls_number_reflns 894 _refine_ls_number_parameters 79 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1036 _refine_ls_R_factor_gt 0.0862 _refine_ls_wR_factor_ref 0.2163 _refine_ls_wR_factor_gt 0.2072 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.981 _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 Br1 Br 0.21373(8) 0.0949(4) 0.7395(2) 0.0931(14) Uani 1 1 d . . . Cu1 Cu 0.2500 0.2500 0.8885(2) 0.0587(14) Uani 1 2 d S . . O15 O 0.3785(7) 0.183(4) 1.177(2) 0.145(10) Uiso 1 1 d . . . O16 O 0.3739(8) -0.111(4) 1.084(2) 0.154(10) Uiso 1 1 d . . . N1 N 0.2836(4) 0.338(3) 1.0022(14) 0.062(5) Uiso 1 1 d . . . N10 N 0.2820(4) 0.063(3) 0.9031(13) 0.055(5) Uiso 1 1 d . . . C2 C 0.2840(6) 0.489(4) 1.0555(17) 0.073(7) Uiso 1 1 d . . . H2 H 0.2677 0.5624 1.0425 0.088 Uiso 1 1 calc R . . C3 C 0.3062(6) 0.523(4) 1.1203(19) 0.078(7) Uiso 1 1 d . . . H3 H 0.3053 0.6210 1.1535 0.094 Uiso 1 1 calc R . . C4 C 0.3304(6) 0.427(3) 1.1426(18) 0.076(7) Uiso 1 1 d . . . H4 H 0.3462 0.4597 1.1890 0.091 Uiso 1 1 calc R . . C5 C 0.3566(6) 0.154(4) 1.1131(17) 0.072(7) Uiso 1 1 d . . . C6 C 0.3549(7) 0.000(4) 1.0676(19) 0.077(8) Uiso 1 1 d . . . C7 C 0.3273(5) -0.171(3) 0.9347(16) 0.058(6) Uiso 1 1 d . . . H7 H 0.3433 -0.2481 0.9435 0.069 Uiso 1 1 calc R . . C8 C 0.3026(6) -0.197(4) 0.8714(19) 0.080(7) Uiso 1 1 d . . . H8 H 0.3004 -0.2950 0.8389 0.095 Uiso 1 1 calc R . . C9 C 0.2798(6) -0.077(3) 0.8533(18) 0.065(6) Uiso 1 1 d . . . H9 H 0.2631 -0.0945 0.8066 0.078 Uiso 1 1 calc R . . C11 C 0.3074(5) 0.240(3) 1.0206(15) 0.055(6) Uiso 1 1 d . . . C12 C 0.3069(5) 0.083(3) 0.9695(13) 0.042(5) Uiso 1 1 d . . . C13 C 0.3322(5) 0.274(3) 1.0958(16) 0.058(6) Uiso 1 1 d . . . C14 C 0.3287(5) -0.027(3) 0.9879(15) 0.051(5) 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 Br1 0.141(3) 0.049(2) 0.0889(18) 0.0183(16) 0.0074(17) 0.039(2) Cu1 0.055(2) 0.058(3) 0.064(2) 0.000 0.000 0.020(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 Br1 Cu1 2.766(4) . ? Cu1 N10 2.06(2) 14 ? Cu1 N10 2.06(2) . ? Cu1 N1 2.153(18) 14 ? Cu1 N1 2.153(19) . ? Cu1 Br1 2.766(4) 14 ? O15 C5 1.25(3) . ? O16 C6 1.23(4) . ? N1 C11 1.30(3) . ? N1 C2 1.44(4) . ? N10 C9 1.34(3) . ? N10 C12 1.35(3) . ? C2 C3 1.28(3) . ? C3 C4 1.31(3) . ? C4 C13 1.42(4) . ? C5 C6 1.42(4) . ? C5 C13 1.44(4) . ? C6 C14 1.51(3) . ? C7 C8 1.33(3) . ? C7 C14 1.40(3) . ? C8 C9 1.39(4) . ? C11 C13 1.44(3) . ? C11 C12 1.47(3) . ? C12 C14 1.31(3) . ? 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 N10 Cu1 N10 169.4(10) 14 . ? N10 Cu1 N1 77.4(8) 14 14 ? N10 Cu1 N1 95.3(8) . 14 ? N10 Cu1 N1 95.3(8) 14 . ? N10 Cu1 N1 77.4(8) . . ? N1 Cu1 N1 93.8(9) 14 . ? N10 Cu1 Br1 94.2(5) 14 . ? N10 Cu1 Br1 93.1(5) . . ? N1 Cu1 Br1 88.1(5) 14 . ? N1 Cu1 Br1 170.5(6) . . ? N10 Cu1 Br1 93.1(5) 14 14 ? N10 Cu1 Br1 94.2(5) . 14 ? N1 Cu1 Br1 170.5(6) 14 14 ? N1 Cu1 Br1 88.1(5) . 14 ? Br1 Cu1 Br1 91.68(16) . 14 ? C11 N1 C2 117(2) . . ? C11 N1 Cu1 113.4(16) . . ? C2 N1 Cu1 129.3(16) . . ? C9 N10 C12 118(2) . . ? C9 N10 Cu1 125.4(15) . . ? C12 N10 Cu1 116.9(16) . . ? C3 C2 N1 121(3) . . ? C2 C3 C4 124(3) . . ? C3 C4 C13 120(2) . . ? O15 C5 C6 119(3) . . ? O15 C5 C13 118(3) . . ? C6 C5 C13 123(2) . . ? O16 C6 C5 126(3) . . ? O16 C6 C14 118(3) . . ? C5 C6 C14 117(3) . . ? C8 C7 C14 118(3) . . ? C7 C8 C9 121(3) . . ? N10 C9 C8 120(2) . . ? N1 C11 C13 122(2) . . ? N1 C11 C12 117.8(19) . . ? C13 C11 C12 120(2) . . ? C14 C12 N10 123(2) . . ? C14 C12 C11 122.2(18) . . ? N10 C12 C11 114(2) . . ? C4 C13 C11 115(2) . . ? C4 C13 C5 127(2) . . ? C11 C13 C5 118(2) . . ? C12 C14 C7 119(2) . . ? C12 C14 C6 121(2) . . ? C7 C14 C6 120(2) . . ? _diffrn_measured_fraction_theta_max 0.883 _diffrn_reflns_theta_full 20.06 _diffrn_measured_fraction_theta_full 0.883 _refine_diff_density_max 0.727 _refine_diff_density_min -0.585 _refine_diff_density_rms 0.154 #===END data_complex_5 _database_code_depnum_ccdc_archive 'CCDC 265319' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(1,10-phenanthroline-5,6-dione)bis(benzene-1-carboxylate-2,3-carboxylic acid) copper(II) 1,3,5-benzene-1,3,5-tricarboxylic acid 2,2,2-trifluoroethanol water clathrate ; _chemical_name_common ; bis(1,10-phenanthroline-5,6-dione)bis(benzene-1-carboxylate- 2,3-carboxylic acid) copper(ii) 1,3,5-benzene-1,3,5-tricarboxylic acid 2,2,2-trifluoroethanol water clathrate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C63.30 H48.95 Cu F4.95 N4 O32.15' _chemical_formula_weight 1537.60 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 14.1807(4) _cell_length_b 16.4770(3) _cell_length_c 16.5025(4) _cell_angle_alpha 60.993(1) _cell_angle_beta 68.484(1) _cell_angle_gamma 81.329(2) _cell_volume 3135.49(13) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour 'pale green' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1575 _exptl_absorpt_coefficient_mu 0.467 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.9124 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 _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 26509 _diffrn_reflns_av_R_equivalents 0.1006 _diffrn_reflns_av_sigmaI/netI 0.0781 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 22.45 _reflns_number_total 7962 _reflns_number_gt 6293 _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^)+(0.1534P)^2^+34.6381P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7962 _refine_ls_number_parameters 916 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1390 _refine_ls_R_factor_gt 0.1176 _refine_ls_wR_factor_ref 0.3370 _refine_ls_wR_factor_gt 0.3207 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.002 _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 0.32003(10) 0.26422(9) 0.23517(9) 0.0366(4) Uani 1 1 d . . . N1 N 0.1696(7) 0.2771(6) 0.2920(6) 0.039(2) Uani 1 1 d . . . C2 C 0.1011(9) 0.2925(8) 0.2470(8) 0.043(3) Uani 1 1 d . . . H2 H 0.1244 0.3004 0.1817 0.052 Uiso 1 1 calc R . . C3 C 0.0008(9) 0.2970(9) 0.2917(9) 0.050(3) Uani 1 1 d . . . H3 H -0.0444 0.3134 0.2559 0.060 Uiso 1 1 calc R . . C5 C -0.0030(9) 0.2250(8) 0.5462(8) 0.041(3) Uani 1 1 d . . . C6 C 0.0766(9) 0.2072(7) 0.5939(9) 0.045(3) Uani 1 1 d . . . C7 C 0.2633(9) 0.1971(7) 0.5711(9) 0.044(3) Uani 1 1 d . . . H7 H 0.2485 0.1828 0.6378 0.053 Uiso 1 1 calc R . . C8 C 0.3611(10) 0.2010(9) 0.5109(10) 0.055(3) Uani 1 1 d . . . H8 H 0.4156 0.1909 0.5348 0.066 Uiso 1 1 calc R . . C9 C 0.3803(9) 0.2197(8) 0.4152(9) 0.045(3) Uani 1 1 d . . . H9 H 0.4484 0.2195 0.3752 0.054 Uiso 1 1 calc R . . N10 N 0.3075(6) 0.2378(6) 0.3768(7) 0.040(2) Uani 1 1 d . . . N21 N 0.2960(7) 0.1170(7) 0.2726(6) 0.046(2) Uani 1 1 d . . . C11 C 0.1340(8) 0.2589(7) 0.3873(8) 0.037(3) Uani 1 1 d . . . C22 C 0.2126(9) 0.0703(9) 0.2989(9) 0.054(3) Uani 1 1 d . . . H22 H 0.1511 0.1027 0.2997 0.065 Uiso 1 1 calc R . . C12 C 0.2132(7) 0.2368(7) 0.4328(7) 0.032(2) Uani 1 1 d . . . C23 C 0.2101(12) -0.0240(10) 0.3257(10) 0.067(4) Uani 1 1 d . . . H23 H 0.1491 -0.0548 0.3425 0.081 Uiso 1 1 calc R . . C13 C 0.0313(8) 0.2572(8) 0.4384(8) 0.040(3) Uani 1 1 d . . . C24 C 0.2999(11) -0.0710(9) 0.3269(9) 0.059(3) Uani 1 1 d . . . H24 H 0.3009 -0.1359 0.3482 0.071 Uiso 1 1 calc R . . C14 C 0.1862(8) 0.2148(7) 0.5322(8) 0.040(3) Uani 1 1 d . . . O5 O -0.0918(6) 0.2119(6) 0.5959(7) 0.059(2) Uani 1 1 d . . . C25 C 0.4856(9) -0.0704(9) 0.2975(8) 0.049(3) Uani 1 1 d . . . O6 O 0.0509(7) 0.1868(6) 0.6806(6) 0.058(2) Uani 1 1 d . . . C26 C 0.5811(10) -0.0123(9) 0.2540(8) 0.054(3) Uani 1 1 d . . . C27 C 0.6573(9) 0.1484(9) 0.1717(8) 0.051(3) Uani 1 1 d . . . H27 H 0.7232 0.1239 0.1610 0.061 Uiso 1 1 calc R . . C28 C 0.6440(9) 0.2424(9) 0.1429(8) 0.053(3) Uani 1 1 d . . . H28 H 0.7013 0.2836 0.1107 0.063 Uiso 1 1 calc R . . C29 C 0.5476(8) 0.2755(8) 0.1611(8) 0.046(3) Uani 1 1 d . . . H29 H 0.5393 0.3394 0.1442 0.055 Uiso 1 1 calc R . . N30 N 0.4637(7) 0.2201(6) 0.2024(6) 0.040(2) Uani 1 1 d . . . C31 C 0.3843(8) 0.0718(8) 0.2683(8) 0.039(3) Uiso 1 1 d . . . C32 C 0.4752(8) 0.1288(8) 0.2297(7) 0.041(3) Uani 1 1 d . . . C33 C 0.3884(9) -0.0217(8) 0.2965(8) 0.045(3) Uani 1 1 d . . . C34 C 0.5708(9) 0.0908(8) 0.2171(8) 0.047(3) Uani 1 1 d . . . O25 O 0.4904(8) -0.1542(6) 0.3327(7) 0.070(3) Uani 1 1 d . . . O26 O 0.6633(7) -0.0483(6) 0.2528(6) 0.059(2) Uani 1 1 d . . . C51 C 0.3467(8) 0.3615(7) 0.0074(7) 0.032(2) Uani 1 1 d . . . O51 O 0.3148(6) 0.3086(5) 0.0994(5) 0.0438(19) Uani 1 1 d . . . C52 C 0.3585(7) 0.3170(7) -0.0563(7) 0.029(2) Uani 1 1 d . . . O52 O 0.3685(6) 0.4464(5) -0.0347(5) 0.0430(19) Uani 1 1 d . . . C53 C 0.3573(7) 0.2198(7) -0.0124(7) 0.030(2) Uani 1 1 d . . . H53 H 0.3491 0.1847 0.0556 0.035 Uiso 1 1 calc R . . O56 O 0.3708(6) 0.0314(5) 0.0692(5) 0.047(2) Uani 1 1 d . . . C54 C 0.3680(7) 0.1740(6) -0.0675(7) 0.027(2) Uani 1 1 d . . . O55 O 0.3805(6) 0.0289(5) -0.0680(5) 0.0410(18) Uani 1 1 d . . . H55 H 0.3818 -0.0285 -0.0319 0.049 Uiso 1 1 calc R . . C56 C 0.3733(7) 0.2244(7) -0.1650(7) 0.028(2) Uani 1 1 d . . . H56 H 0.3782 0.1938 -0.2025 0.034 Uiso 1 1 calc R . . O58 O 0.3667(6) 0.3284(5) -0.3518(5) 0.0407(18) Uani 1 1 d . . . H58 H 0.3696 0.3633 -0.4103 0.049 Uiso 1 1 calc R . . C57 C 0.3714(7) 0.3214(7) -0.2071(7) 0.026(2) Uani 1 1 d . . . O59 O 0.3852(6) 0.4625(5) -0.3556(5) 0.0396(18) Uani 1 1 d . . . C59 C 0.3659(7) 0.3675(7) -0.1539(7) 0.027(2) Uani 1 1 d . . . H59 H 0.3673 0.4334 -0.1846 0.033 Uiso 1 1 calc R . . C55 C 0.3723(8) 0.0719(7) -0.0190(7) 0.034(2) Uani 1 1 d . . . C58 C 0.3757(7) 0.3786(7) -0.3131(7) 0.030(2) Uani 1 1 d . . . C41 C 0.3783(8) 0.4950(7) 0.1348(7) 0.032(2) Uani 1 1 d . . . O41 O 0.3814(6) 0.4108(5) 0.1825(5) 0.0394(18) Uani 1 1 d . . . C42 C 0.3832(7) 0.5559(7) 0.1769(7) 0.029(2) Uani 1 1 d . . . O40 O 0.3714(6) 0.5373(5) 0.0479(5) 0.0395(18) Uani 1 1 d . . . C43 C 0.3850(7) 0.6520(7) 0.1253(7) 0.028(2) Uani 1 1 d . . . H43 H 0.3871 0.6815 0.0589 0.034 Uiso 1 1 calc R . . O46 O 0.3859(5) 0.8461(5) 0.0271(5) 0.0375(17) Uani 1 1 d . . . C44 C 0.3837(7) 0.7059(6) 0.1702(7) 0.028(2) Uani 1 1 d . . . O45 O 0.3789(6) 0.8525(5) 0.1615(5) 0.0405(18) Uani 1 1 d . . . H45 H 0.3783 0.9096 0.1240 0.049 Uiso 1 1 calc R . . C46 C 0.3817(7) 0.6622(7) 0.2678(7) 0.028(2) Uani 1 1 d . . . H46 H 0.3810 0.6983 0.2986 0.034 Uiso 1 1 calc R . . O48 O 0.3831(6) 0.5668(5) 0.4613(5) 0.0398(18) Uani 1 1 d . . . H48 H 0.3803 0.5332 0.5201 0.048 Uiso 1 1 calc R . . C47 C 0.3808(7) 0.5650(7) 0.3200(7) 0.028(2) Uani 1 1 d . . . O21 O 0.3717(7) 0.4298(5) 0.4679(5) 0.048(2) Uani 1 1 d . . . C49 C 0.3819(7) 0.5134(6) 0.2743(7) 0.026(2) Uani 1 1 d . . . H49 H 0.3817 0.4476 0.3096 0.031 Uiso 1 1 calc R . . C48 C 0.3778(8) 0.5145(8) 0.4239(7) 0.034(2) Uani 1 1 d . . . C45 C 0.3824(7) 0.8078(7) 0.1167(7) 0.032(2) Uani 1 1 d . . . C71 C 0.8749(7) 0.4331(7) -0.3711(7) 0.031(2) Uani 1 1 d . . . O72 O 0.8748(7) 0.3931(5) -0.4180(5) 0.051(2) Uani 1 1 d . . . C72 C 0.8703(7) 0.3793(7) -0.2677(7) 0.030(2) Uani 1 1 d . . . O71 O 0.8765(6) 0.5229(5) -0.4080(5) 0.0415(18) Uani 1 1 d . . . H71 H 0.8790 0.5473 -0.4668 0.050 Uiso 1 1 calc R . . C73 C 0.8673(7) 0.2817(7) -0.2221(7) 0.026(2) Uani 1 1 d . . . H73 H 0.8681 0.2500 -0.2576 0.031 Uiso 1 1 calc R . . O75 O 0.8516(6) 0.0887(5) -0.1204(5) 0.0378(17) Uani 1 1 d . . . H75 H 0.8507 0.0308 -0.0861 0.045 Uiso 1 1 calc R . . C74 C 0.8631(7) 0.2322(7) -0.1247(7) 0.027(2) Uani 1 1 d . . . O76 O 0.8681(6) 0.0870(5) 0.0100(5) 0.047(2) Uani 1 1 d . . . C76 C 0.8626(7) 0.2786(7) -0.0728(7) 0.026(2) Uani 1 1 d . . . H76 H 0.8609 0.2443 -0.0064 0.032 Uiso 1 1 calc R . . O79 O 0.8647(5) 0.3789(5) 0.0240(5) 0.0382(17) Uani 1 1 d . . . C77 C 0.8648(7) 0.3754(7) -0.1186(7) 0.027(2) Uani 1 1 d . . . O78 O 0.8717(6) 0.5118(5) -0.1113(5) 0.049(2) Uani 1 1 d . . . H78 H 0.8723 0.5343 -0.0754 0.059 Uiso 1 1 calc R . . C79 C 0.8688(7) 0.4257(7) -0.2157(7) 0.028(2) Uani 1 1 d . . . H89 H 0.8706 0.4917 -0.2467 0.033 Uiso 1 1 calc R . . C78 C 0.8670(7) 0.4247(7) -0.0633(7) 0.029(2) Uani 1 1 d . . . C75 C 0.8613(7) 0.1288(7) -0.0724(7) 0.029(2) Uani 1 1 d . . . C61 C 0.1148(8) 0.4389(7) -0.0618(7) 0.032(2) Uani 1 1 d . . . O62 O 0.1193(6) 0.3957(5) 0.0233(5) 0.0405(18) Uani 1 1 d . . . C62 C 0.1147(7) 0.3858(6) -0.1137(7) 0.025(2) Uani 1 1 d . . . O61 O 0.1112(6) 0.5259(5) -0.1083(5) 0.0457(19) Uani 1 1 d . . . H61 H 0.1113 0.5492 -0.0730 0.055 Uiso 1 1 calc R . . C69 C 0.1157(7) 0.2885(7) -0.0652(7) 0.028(2) Uani 1 1 d . . . H69 H 0.1145 0.2566 0.0010 0.034 Uiso 1 1 calc R . . O65 O 0.1217(6) 0.5229(5) -0.4003(5) 0.049(2) Uani 1 1 d . . . H65 H 0.1228 0.5464 -0.4586 0.058 Uiso 1 1 calc R . . C67 C 0.1184(7) 0.2390(6) -0.1140(7) 0.026(2) Uani 1 1 d . . . O66 O 0.1222(6) 0.3911(5) -0.4084(5) 0.0404(18) Uani 1 1 d . . . C66 C 0.1194(7) 0.2857(7) -0.2114(7) 0.028(2) Uani 1 1 d . . . H66 H 0.1197 0.2517 -0.2443 0.034 Uiso 1 1 calc R . . O69 O 0.1351(5) 0.0954(4) 0.0178(5) 0.0358(17) Uani 1 1 d . . . C64 C 0.1199(7) 0.3839(7) -0.2604(6) 0.026(2) Uani 1 1 d . . . O68 O 0.1192(6) 0.0960(5) -0.1130(5) 0.046(2) Uani 1 1 d . . . H68 H 0.1232 0.0384 -0.0805 0.055 Uiso 1 1 calc R . . C63 C 0.1182(7) 0.4329(7) -0.2114(7) 0.027(2) Uani 1 1 d . . . H63 H 0.1195 0.4989 -0.2445 0.032 Uiso 1 1 calc R . . C68 C 0.1244(7) 0.1361(7) -0.0636(7) 0.030(2) Uani 1 1 d . . . C65 C 0.1218(7) 0.4322(7) -0.3623(7) 0.031(2) Uani 1 1 d . . . F5B F -0.086(2) 0.132(2) 0.153(2) 0.104(5) Uiso 0.40 1 d P A 2 F4A F 0.0080(15) 0.0785(14) 0.2352(14) 0.105(3) Uiso 0.60 1 d P A 1 C90 C -0.0776(15) 0.0847(14) 0.2368(14) 0.094(5) Uiso 1 1 d . . . C91 C -0.1603(18) 0.0525(17) 0.3318(18) 0.126(7) Uiso 0.50 1 d PD A 1 H91A H -0.1506 -0.0125 0.3771 0.151 Uiso 0.50 1 calc PR A 1 H91B H -0.2264 0.0558 0.3229 0.151 Uiso 0.50 1 calc PR A 1 C4 C -0.0363(9) 0.2777(9) 0.3895(9) 0.050(3) Uani 1 1 d . . . H4 H -0.1070 0.2786 0.4222 0.060 Uiso 1 1 calc R . . F2 F -0.3937(14) 0.3647(13) 0.2975(13) 0.117(5) Uiso 0.65 1 d P . . F1 F -0.2598(12) 0.3042(11) 0.2590(12) 0.100(4) Uiso 0.65 1 d P . . F3 F -0.2662(14) 0.3754(13) 0.3367(14) 0.121(6) Uiso 0.65 1 d P . . C80 C -0.3205(17) 0.3234(16) 0.3281(16) 0.064(5) Uiso 0.65 1 d P . . C81 C -0.353(2) 0.252(2) 0.423(2) 0.094(8) Uiso 0.65 1 d P . . H81A H -0.4057 0.2736 0.4664 0.112 Uiso 0.65 1 calc PR . . H81B H -0.3833 0.2005 0.4241 0.112 Uiso 0.65 1 calc PR . . O90 O -0.1025(14) -0.0363(13) 0.4047(14) 0.065(5) Uiso 0.50 1 d P A 2 H90 H -0.0413 -0.0369 0.3717 0.078 Uiso 0.50 1 calc PR A 2 O91 O -0.1567(16) 0.1183(15) 0.3736(16) 0.079(6) Uiso 0.50 1 d PD A 1 H91 H -0.0969 0.1387 0.3520 0.095 Uiso 0.50 1 calc PR A 1 O81 O -0.2735(19) 0.2223(18) 0.4534(19) 0.129(7) Uiso 0.65 1 d P . . H81 H -0.2370 0.1908 0.4266 0.154 Uiso 0.65 1 calc PR . . F4B F 0.009(2) 0.126(2) 0.231(2) 0.104(5) Uiso 0.40 1 d P A 2 F5A F -0.0963(14) 0.1699(14) 0.1689(14) 0.105(3) Uiso 0.60 1 d P A 1 F6A F -0.0988(14) 0.0372(13) 0.1928(13) 0.105(3) Uiso 0.60 1 d P A 1 O101 O -0.0226(9) 0.0660(9) 0.4586(9) 0.031(3) Uiso 0.50 1 d P . . O102 O 0.4790(10) -0.0147(10) 0.4444(10) 0.035(3) Uiso 0.50 1 d P B 1 F6B F -0.020(2) 0.0148(19) 0.206(2) 0.104(5) Uiso 0.40 1 d P A 2 O104 O 0.5742(14) 0.0886(13) 0.4046(14) 0.068(5) Uiso 0.50 1 d P C 1 O103 O 0.5139(15) 0.0191(14) 0.4566(13) 0.069(5) Uiso 0.50 1 d P . 2 O100 O -0.0581(15) -0.0616(14) 0.4615(15) 0.071(5) Uiso 0.50 1 d P D 1 C91A C -0.1603(18) 0.0525(17) 0.3318(18) 0.126(7) Uiso 0.50 1 d P A 2 H91C H -0.2204 0.0302 0.3304 0.151 Uiso 0.50 1 calc PR A 2 H91D H -0.1802 0.1014 0.3529 0.151 Uiso 0.50 1 calc PR A 2 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 0.0438(8) 0.0351(8) 0.0275(7) -0.0138(6) -0.0115(6) 0.0054(6) N1 0.049(6) 0.036(5) 0.028(5) -0.011(4) -0.017(4) 0.007(4) C2 0.049(7) 0.043(7) 0.038(6) -0.018(5) -0.020(6) 0.007(5) C3 0.053(8) 0.054(8) 0.050(7) -0.022(6) -0.032(6) 0.010(6) C5 0.041(7) 0.047(7) 0.042(6) -0.031(6) -0.004(5) -0.002(5) C6 0.063(8) 0.027(6) 0.042(7) -0.017(5) -0.012(6) -0.001(5) C7 0.053(8) 0.035(6) 0.051(7) -0.022(6) -0.027(6) 0.013(5) C8 0.063(9) 0.055(8) 0.068(9) -0.034(7) -0.040(7) 0.013(6) C9 0.039(7) 0.036(6) 0.053(8) -0.018(6) -0.012(6) 0.002(5) N10 0.032(5) 0.043(6) 0.047(5) -0.017(5) -0.020(5) 0.003(4) N21 0.048(6) 0.046(6) 0.035(5) -0.016(5) -0.010(4) 0.006(5) C11 0.048(7) 0.030(6) 0.036(6) -0.015(5) -0.018(5) 0.006(5) C22 0.041(7) 0.056(8) 0.056(8) -0.021(7) -0.013(6) -0.003(6) C12 0.034(6) 0.028(6) 0.036(6) -0.017(5) -0.011(5) -0.001(4) C23 0.073(10) 0.055(9) 0.062(9) -0.021(7) -0.018(7) -0.003(7) C13 0.032(6) 0.040(6) 0.054(7) -0.029(6) -0.012(5) 0.003(5) C24 0.082(10) 0.044(8) 0.055(8) -0.025(7) -0.024(7) 0.003(7) C14 0.053(7) 0.027(6) 0.047(7) -0.018(5) -0.022(6) 0.000(5) O5 0.050(6) 0.070(6) 0.069(6) -0.048(5) -0.010(5) -0.001(4) C25 0.063(8) 0.045(8) 0.034(6) -0.019(6) -0.015(6) 0.013(6) O6 0.077(6) 0.058(6) 0.038(5) -0.030(4) -0.012(4) 0.010(4) C26 0.067(9) 0.055(8) 0.029(6) -0.015(6) -0.017(6) 0.015(7) C27 0.049(7) 0.058(8) 0.035(6) -0.020(6) -0.011(6) 0.011(6) C28 0.041(7) 0.060(9) 0.035(6) -0.013(6) 0.000(5) -0.006(6) C29 0.043(7) 0.040(7) 0.039(6) -0.012(6) -0.005(5) -0.002(6) N30 0.055(6) 0.036(6) 0.022(4) -0.012(4) -0.010(4) 0.009(5) C32 0.041(7) 0.047(7) 0.024(5) -0.013(5) -0.011(5) 0.013(5) C33 0.059(8) 0.039(7) 0.029(6) -0.014(5) -0.012(5) 0.006(6) C34 0.055(8) 0.051(8) 0.028(6) -0.017(6) -0.011(5) 0.003(6) O25 0.089(7) 0.046(6) 0.056(6) -0.021(5) -0.016(5) 0.019(5) O26 0.066(6) 0.056(5) 0.057(5) -0.032(5) -0.026(4) 0.030(5) C51 0.040(6) 0.037(7) 0.023(6) -0.016(5) -0.012(4) 0.003(5) O51 0.058(5) 0.050(5) 0.033(5) -0.027(4) -0.015(4) 0.002(4) C52 0.032(5) 0.033(6) 0.025(5) -0.013(5) -0.013(4) -0.001(4) O52 0.065(5) 0.037(5) 0.039(4) -0.026(4) -0.017(4) -0.002(4) C53 0.033(6) 0.033(6) 0.025(5) -0.013(5) -0.014(4) 0.004(4) O56 0.078(6) 0.032(4) 0.037(5) -0.012(4) -0.032(4) 0.000(4) C54 0.030(5) 0.025(5) 0.026(5) -0.013(4) -0.011(4) 0.004(4) O55 0.070(5) 0.024(4) 0.034(4) -0.016(3) -0.020(4) 0.005(3) C56 0.032(5) 0.032(6) 0.027(5) -0.017(5) -0.014(4) 0.005(4) O58 0.065(5) 0.035(4) 0.026(4) -0.013(3) -0.022(3) 0.005(4) C57 0.025(5) 0.031(6) 0.025(5) -0.013(4) -0.010(4) 0.000(4) O59 0.064(5) 0.022(4) 0.027(4) -0.004(3) -0.020(3) 0.000(3) C59 0.025(5) 0.031(6) 0.029(5) -0.013(5) -0.012(4) 0.001(4) C55 0.048(6) 0.030(6) 0.027(6) -0.012(5) -0.018(5) 0.001(5) C58 0.031(6) 0.036(7) 0.022(5) -0.014(5) -0.011(4) 0.007(4) C41 0.038(6) 0.029(6) 0.029(6) -0.015(5) -0.012(5) 0.005(4) O41 0.063(5) 0.029(5) 0.039(4) -0.018(4) -0.028(4) 0.004(3) C42 0.029(5) 0.028(6) 0.031(5) -0.012(5) -0.015(4) 0.003(4) O40 0.061(5) 0.033(4) 0.030(4) -0.017(3) -0.020(3) 0.007(3) C43 0.027(5) 0.036(6) 0.026(5) -0.015(5) -0.013(4) 0.003(4) O46 0.056(5) 0.033(4) 0.025(4) -0.010(3) -0.020(3) 0.001(3) C44 0.031(5) 0.025(5) 0.028(5) -0.012(5) -0.012(4) 0.003(4) O45 0.070(5) 0.026(4) 0.038(4) -0.018(3) -0.031(4) 0.010(3) C46 0.027(5) 0.034(6) 0.026(5) -0.016(5) -0.010(4) 0.003(4) O48 0.063(5) 0.039(4) 0.023(4) -0.017(3) -0.017(3) 0.003(3) C47 0.032(5) 0.027(6) 0.024(5) -0.012(5) -0.011(4) 0.004(4) O21 0.089(6) 0.026(5) 0.031(4) -0.006(4) -0.029(4) -0.002(4) C49 0.036(6) 0.016(5) 0.025(5) -0.006(4) -0.013(4) 0.000(4) C48 0.037(6) 0.039(7) 0.028(5) -0.015(5) -0.014(5) 0.004(5) C45 0.031(6) 0.029(6) 0.026(6) -0.006(5) -0.009(4) 0.001(4) C71 0.033(6) 0.034(6) 0.028(5) -0.015(5) -0.009(4) -0.002(4) O72 0.095(6) 0.040(5) 0.034(4) -0.021(4) -0.035(4) 0.005(4) C72 0.026(5) 0.040(6) 0.033(6) -0.023(5) -0.013(4) 0.003(4) O71 0.068(5) 0.031(4) 0.028(4) -0.012(3) -0.019(4) -0.003(4) C73 0.023(5) 0.033(6) 0.026(5) -0.016(5) -0.010(4) 0.003(4) O75 0.060(5) 0.025(4) 0.033(4) -0.012(3) -0.023(3) 0.001(3) C74 0.022(5) 0.030(6) 0.031(5) -0.013(5) -0.013(4) 0.003(4) O76 0.084(6) 0.031(4) 0.039(5) -0.020(4) -0.034(4) 0.012(4) C76 0.023(5) 0.037(6) 0.023(5) -0.019(5) -0.004(4) -0.002(4) O79 0.056(5) 0.039(4) 0.025(4) -0.018(3) -0.016(3) 0.004(3) C77 0.029(5) 0.031(6) 0.025(5) -0.016(5) -0.009(4) 0.003(4) O78 0.090(6) 0.031(5) 0.030(4) -0.015(4) -0.019(4) -0.010(4) C79 0.032(5) 0.025(5) 0.026(5) -0.011(4) -0.012(4) 0.000(4) C78 0.028(5) 0.036(7) 0.030(6) -0.020(5) -0.009(4) 0.002(4) C75 0.031(5) 0.034(6) 0.031(6) -0.021(5) -0.013(4) 0.006(4) C61 0.040(6) 0.028(6) 0.031(6) -0.015(5) -0.014(5) 0.004(4) O62 0.074(5) 0.030(4) 0.029(4) -0.017(3) -0.026(4) 0.006(4) C62 0.029(5) 0.031(6) 0.027(5) -0.020(5) -0.013(4) 0.004(4) O61 0.079(6) 0.034(5) 0.040(4) -0.021(4) -0.034(4) 0.007(4) C69 0.025(5) 0.036(6) 0.028(5) -0.018(5) -0.011(4) 0.002(4) O65 0.087(6) 0.038(5) 0.034(4) -0.020(4) -0.032(4) 0.007(4) C67 0.026(5) 0.026(5) 0.028(5) -0.013(4) -0.011(4) 0.002(4) O66 0.072(5) 0.028(4) 0.027(4) -0.016(3) -0.018(4) 0.001(3) C66 0.028(5) 0.038(6) 0.026(5) -0.020(5) -0.008(4) -0.001(4) O69 0.054(5) 0.023(4) 0.034(4) -0.012(3) -0.022(3) 0.001(3) C64 0.027(5) 0.036(6) 0.022(5) -0.017(5) -0.010(4) -0.001(4) O68 0.086(6) 0.026(4) 0.037(4) -0.016(3) -0.034(4) 0.007(4) C63 0.029(5) 0.024(5) 0.033(6) -0.014(5) -0.016(4) 0.003(4) C68 0.033(6) 0.033(6) 0.032(6) -0.019(5) -0.016(4) 0.008(4) C65 0.030(6) 0.029(6) 0.039(6) -0.020(5) -0.011(4) 0.003(4) C4 0.037(7) 0.065(8) 0.059(8) -0.039(7) -0.015(6) 0.009(6) _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 N1 2.016(9) . ? Cu1 O51 2.019(7) . ? Cu1 N30 2.025(9) . ? Cu1 N10 2.101(9) . ? Cu1 N21 2.241(10) . ? Cu1 O41 2.321(7) . ? N1 C11 1.351(13) . ? N1 C2 1.353(14) . ? C2 C3 1.351(16) . ? C3 C4 1.384(17) . ? C5 O5 1.207(13) . ? C5 C13 1.488(16) . ? C5 C6 1.519(17) . ? C6 O6 1.216(13) . ? C6 C14 1.497(16) . ? C7 C8 1.367(17) . ? C7 C14 1.390(15) . ? C8 C9 1.378(17) . ? C9 N10 1.326(14) . ? N10 C12 1.315(13) . ? N21 C22 1.325(15) . ? N21 C31 1.353(14) . ? C11 C13 1.386(15) . ? C11 C12 1.480(14) . ? C22 C23 1.396(19) . ? C12 C14 1.405(15) . ? C23 C24 1.389(19) . ? C13 C4 1.374(16) . ? C24 C33 1.392(18) . ? C25 O25 1.213(14) . ? C25 C33 1.488(17) . ? C25 C26 1.509(19) . ? C26 O26 1.224(14) . ? C26 C34 1.504(18) . ? C27 C28 1.386(18) . ? C27 C34 1.398(17) . ? C28 C29 1.376(16) . ? C29 N30 1.357(14) . ? N30 C32 1.346(14) . ? C31 C33 1.375(16) . ? C31 C32 1.460(16) . ? C32 C34 1.393(16) . ? C51 O52 1.251(12) . ? C51 O51 1.264(12) . ? C51 C52 1.502(14) . ? C52 C59 1.378(13) . ? C52 C53 1.402(14) . ? C53 C54 1.395(13) . ? O56 C55 1.267(12) . ? C54 C56 1.385(13) . ? C54 C55 1.475(14) . ? O55 C55 1.277(12) . ? C56 C57 1.401(14) . ? O58 C58 1.307(12) . ? C57 C59 1.391(13) . ? C57 C58 1.514(13) . ? O59 C58 1.212(12) . ? C41 O41 1.223(12) . ? C41 O40 1.291(12) . ? C41 C42 1.491(14) . ? C42 C43 1.386(14) . ? C42 C49 1.401(13) . ? C43 C44 1.401(13) . ? O46 C45 1.279(12) . ? C44 C46 1.401(13) . ? C44 C45 1.471(14) . ? O45 C45 1.258(12) . ? C46 C47 1.402(14) . ? O48 C48 1.304(12) . ? C47 C49 1.378(13) . ? C47 C48 1.486(14) . ? O21 C48 1.219(12) . ? C71 O72 1.236(12) . ? C71 O71 1.299(12) . ? C71 C72 1.474(14) . ? C72 C79 1.394(13) . ? C72 C73 1.406(14) . ? C73 C74 1.388(13) . ? O75 C75 1.304(11) . ? C74 C76 1.397(13) . ? C74 C75 1.489(14) . ? O76 C75 1.224(12) . ? C76 C77 1.395(14) . ? O79 C78 1.250(12) . ? C77 C79 1.384(13) . ? C77 C78 1.496(13) . ? O78 C78 1.257(12) . ? C61 O62 1.252(12) . ? C61 O61 1.258(12) . ? C61 C62 1.492(13) . ? C62 C63 1.394(13) . ? C62 C69 1.404(14) . ? C69 C67 1.385(13) . ? O65 C65 1.311(12) . ? C67 C66 1.401(13) . ? C67 C68 1.489(14) . ? O66 C65 1.238(11) . ? C66 C64 1.414(14) . ? O69 C68 1.233(11) . ? C64 C63 1.386(13) . ? C64 C65 1.461(14) . ? O68 C68 1.299(12) . ? F5B C90 1.26(3) . ? F4A C90 1.19(2) . ? C90 F5A 1.37(3) . ? C90 F6A 1.42(2) . ? C90 F4B 1.44(3) . ? C90 C91 1.47(3) . ? C90 F6B 1.50(3) . ? C91 O91 1.56(3) . ? F2 C80 1.28(2) . ? F1 C80 1.30(2) . ? F3 C80 1.32(3) . ? C80 C81 1.37(3) . ? C81 O81 1.34(3) . ? O103 O103 1.18(3) 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 N1 Cu1 O51 92.8(3) . . ? N1 Cu1 N30 166.6(4) . . ? O51 Cu1 N30 94.2(3) . . ? N1 Cu1 N10 79.6(3) . . ? O51 Cu1 N10 169.6(3) . . ? N30 Cu1 N10 94.7(3) . . ? N1 Cu1 N21 91.0(4) . . ? O51 Cu1 N21 90.3(3) . . ? N30 Cu1 N21 77.6(4) . . ? N10 Cu1 N21 96.9(3) . . ? N1 Cu1 O41 101.3(3) . . ? O51 Cu1 O41 88.9(3) . . ? N30 Cu1 O41 90.2(3) . . ? N10 Cu1 O41 85.7(3) . . ? N21 Cu1 O41 167.6(3) . . ? C11 N1 C2 117.8(9) . . ? C11 N1 Cu1 115.9(7) . . ? C2 N1 Cu1 125.9(7) . . ? C3 C2 N1 122.3(10) . . ? C2 C3 C4 120.1(10) . . ? O5 C5 C13 121.5(10) . . ? O5 C5 C6 120.0(10) . . ? C13 C5 C6 118.5(10) . . ? O6 C6 C14 121.3(11) . . ? O6 C6 C5 120.1(11) . . ? C14 C6 C5 118.6(10) . . ? C8 C7 C14 118.1(11) . . ? C7 C8 C9 119.7(11) . . ? N10 C9 C8 122.7(11) . . ? C12 N10 C9 118.4(9) . . ? C12 N10 Cu1 112.9(6) . . ? C9 N10 Cu1 128.7(8) . . ? C22 N21 C31 118.3(10) . . ? C22 N21 Cu1 131.0(8) . . ? C31 N21 Cu1 110.7(7) . . ? N1 C11 C13 122.2(10) . . ? N1 C11 C12 114.3(9) . . ? C13 C11 C12 123.5(9) . . ? N21 C22 C23 123.5(12) . . ? N10 C12 C14 122.8(9) . . ? N10 C12 C11 117.2(9) . . ? C14 C12 C11 120.1(9) . . ? C24 C23 C22 117.6(13) . . ? C4 C13 C11 118.9(10) . . ? C4 C13 C5 121.9(10) . . ? C11 C13 C5 119.0(10) . . ? C23 C24 C33 119.1(12) . . ? C7 C14 C12 118.1(10) . . ? C7 C14 C6 122.0(10) . . ? C12 C14 C6 119.9(10) . . ? O25 C25 C33 122.7(12) . . ? O25 C25 C26 119.3(11) . . ? C33 C25 C26 118.0(11) . . ? O26 C26 C34 121.2(12) . . ? O26 C26 C25 121.0(12) . . ? C34 C26 C25 117.7(11) . . ? C28 C27 C34 118.1(11) . . ? C29 C28 C27 119.6(11) . . ? N30 C29 C28 122.3(11) . . ? C32 N30 C29 118.9(10) . . ? C32 N30 Cu1 117.1(7) . . ? C29 N30 Cu1 123.9(8) . . ? N21 C31 C33 122.1(10) . . ? N21 C31 C32 115.9(10) . . ? C33 C31 C32 122.1(10) . . ? N30 C32 C34 121.3(11) . . ? N30 C32 C31 117.7(9) . . ? C34 C32 C31 120.9(11) . . ? C31 C33 C24 119.2(11) . . ? C31 C33 C25 120.5(11) . . ? C24 C33 C25 120.2(11) . . ? C32 C34 C27 119.8(11) . . ? C32 C34 C26 120.2(11) . . ? C27 C34 C26 120.1(11) . . ? O52 C51 O51 126.4(9) . . ? O52 C51 C52 117.6(8) . . ? O51 C51 C52 116.0(9) . . ? C51 O51 Cu1 150.8(7) . . ? C59 C52 C53 119.4(9) . . ? C59 C52 C51 122.7(9) . . ? C53 C52 C51 117.8(8) . . ? C54 C53 C52 120.7(9) . . ? C56 C54 C53 120.0(9) . . ? C56 C54 C55 121.5(8) . . ? C53 C54 C55 118.4(8) . . ? C54 C56 C57 118.5(8) . . ? C59 C57 C56 121.6(8) . . ? C59 C57 C58 118.4(9) . . ? C56 C57 C58 120.0(8) . . ? C52 C59 C57 119.6(9) . . ? O56 C55 O55 123.2(9) . . ? O56 C55 C54 117.6(9) . . ? O55 C55 C54 119.1(8) . . ? O59 C58 O58 124.7(9) . . ? O59 C58 C57 122.0(9) . . ? O58 C58 C57 113.2(9) . . ? O41 C41 O40 124.6(9) . . ? O41 C41 C42 119.7(9) . . ? O40 C41 C42 115.8(9) . . ? C41 O41 Cu1 148.4(7) . . ? C43 C42 C49 119.0(9) . . ? C43 C42 C41 122.8(8) . . ? C49 C42 C41 118.1(8) . . ? C42 C43 C44 120.6(9) . . ? C43 C44 C46 119.6(9) . . ? C43 C44 C45 120.8(8) . . ? C46 C44 C45 119.6(9) . . ? C44 C46 C47 120.0(9) . . ? C49 C47 C46 119.4(8) . . ? C49 C47 C48 118.0(9) . . ? C46 C47 C48 122.6(9) . . ? C47 C49 C42 121.5(9) . . ? O21 C48 O48 124.4(9) . . ? O21 C48 C47 120.3(9) . . ? O48 C48 C47 115.3(9) . . ? O45 C45 O46 123.6(9) . . ? O45 C45 C44 118.0(8) . . ? O46 C45 C44 118.4(9) . . ? O72 C71 O71 123.0(9) . . ? O72 C71 C72 120.4(9) . . ? O71 C71 C72 116.5(8) . . ? C79 C72 C73 120.5(9) . . ? C79 C72 C71 119.6(9) . . ? C73 C72 C71 120.0(8) . . ? C74 C73 C72 119.2(9) . . ? C73 C74 C76 120.5(9) . . ? C73 C74 C75 122.0(8) . . ? C76 C74 C75 117.5(8) . . ? C77 C76 C74 119.8(8) . . ? C79 C77 C76 120.4(8) . . ? C79 C77 C78 120.1(9) . . ? C76 C77 C78 119.5(8) . . ? C77 C79 C72 119.7(9) . . ? O79 C78 O78 125.0(9) . . ? O79 C78 C77 119.9(9) . . ? O78 C78 C77 115.1(8) . . ? O76 C75 O75 124.2(9) . . ? O76 C75 C74 120.7(8) . . ? O75 C75 C74 115.1(8) . . ? O62 C61 O61 124.2(9) . . ? O62 C61 C62 119.1(9) . . ? O61 C61 C62 116.7(9) . . ? C63 C62 C69 120.2(8) . . ? C63 C62 C61 120.1(9) . . ? C69 C62 C61 119.7(8) . . ? C67 C69 C62 119.9(9) . . ? C69 C67 C66 120.3(9) . . ? C69 C67 C68 119.5(8) . . ? C66 C67 C68 120.2(8) . . ? C67 C66 C64 119.6(8) . . ? C63 C64 C66 119.8(8) . . ? C63 C64 C65 120.9(9) . . ? C66 C64 C65 119.3(8) . . ? C64 C63 C62 120.2(9) . . ? O69 C68 O68 125.0(9) . . ? O69 C68 C67 120.6(8) . . ? O68 C68 C67 114.5(8) . . ? O66 C65 O65 122.8(9) . . ? O66 C65 C64 123.1(9) . . ? O65 C65 C64 114.1(8) . . ? F4A C90 F5B 113(2) . . ? F4A C90 F5A 112.8(19) . . ? F5B C90 F5A 33.7(14) . . ? F4A C90 F6A 113.5(19) . . ? F5B C90 F6A 61.6(17) . . ? F5A C90 F6A 93.3(17) . . ? F4A C90 F4B 31.5(14) . . ? F5B C90 F4B 105(2) . . ? F5A C90 F4B 88.9(18) . . ? F6A C90 F4B 138(2) . . ? F4A C90 C91 119(2) . . ? F5B C90 C91 127(2) . . ? F5A C90 C91 111.5(19) . . ? F6A C90 C91 103.2(17) . . ? F4B C90 C91 115(2) . . ? F4A C90 F6B 66.7(17) . . ? F5B C90 F6B 89(2) . . ? F5A C90 F6B 121(2) . . ? F6A C90 F6B 47.9(12) . . ? F4B C90 F6B 96(2) . . ? C91 C90 F6B 119.0(19) . . ? C90 C91 O91 106.0(18) . . ? C13 C4 C3 118.6(11) . . ? F2 C80 F1 104.7(19) . . ? F2 C80 F3 115(2) . . ? F1 C80 F3 105.8(19) . . ? F2 C80 C81 113(2) . . ? F1 C80 C81 118(2) . . ? F3 C80 C81 101(2) . . ? O81 C81 C80 108(2) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 22.45 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 2.584 _refine_diff_density_min -0.877 _refine_diff_density_rms 0.144 #===END data_complex_6 _database_code_depnum_ccdc_archive 'CCDC 265320' _audit_creation_method SHELXL-97 _chemical_name_systematic ; tetra(benzene-1-carboxylate-3,5-carboxylic acid)bis(1,10-phenanthroline) dicopper(II)benzene-1,3,5-carboxylic acid ; _chemical_name_common ; tetra(benzene-1-carboxylate-3,5-carboxylic acid)bis(1,10- phenanthroline) dicopper(ii)benzene-1,3,5-carboxylic acid ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H24 Cu N2 O18' _chemical_formula_weight 872.14 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.814(2) _cell_length_b 13.632(3) _cell_length_c 15.322(3) _cell_angle_alpha 68.78(3) _cell_angle_beta 79.24(3) _cell_angle_gamma 76.93(3) _cell_volume 2225.7(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 890 _exptl_absorpt_coefficient_mu 0.563 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.8957 _exptl_absorpt_correction_T_max 0.9153 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 _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 26730 _diffrn_reflns_av_R_equivalents 0.1590 _diffrn_reflns_av_sigmaI/netI 0.1235 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7746 _reflns_number_gt 5182 _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. Data was subjected to the SQUEEZE routine. ; _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^)+(0.1736P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7746 _refine_ls_number_parameters 541 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1208 _refine_ls_R_factor_gt 0.0938 _refine_ls_wR_factor_ref 0.2707 _refine_ls_wR_factor_gt 0.2506 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 0.42948(5) 0.62801(5) 0.36507(4) 0.0531(3) Uani 1 1 d . . . N1 N 0.2806(4) 0.7363(3) 0.3350(3) 0.0544(11) Uani 1 1 d . . . C2 C 0.1726(5) 0.7183(5) 0.3388(4) 0.0605(15) Uani 1 1 d . . . H2 H 0.1590 0.6467 0.3613 0.073 Uiso 1 1 calc R . . C3 C 0.0795(5) 0.8017(5) 0.3108(4) 0.0643(16) Uani 1 1 d . . . H3 H 0.0035 0.7867 0.3153 0.077 Uiso 1 1 calc R . . C4 C 0.0978(6) 0.9052(5) 0.2767(4) 0.0653(16) Uani 1 1 d . . . H4 H 0.0348 0.9624 0.2572 0.078 Uiso 1 1 calc R . . C5 C 0.2404(6) 1.0315(5) 0.2354(4) 0.0732(18) Uani 1 1 d . . . H5 H 0.1815 1.0920 0.2139 0.088 Uiso 1 1 calc R . . C6 C 0.3535(7) 1.0460(5) 0.2323(4) 0.0739(19) Uani 1 1 d . . . H6 H 0.3714 1.1161 0.2086 0.089 Uiso 1 1 calc R . . C7 C 0.5614(7) 0.9612(5) 0.2653(4) 0.0741(18) Uani 1 1 d . . . H7 H 0.5853 1.0290 0.2429 0.089 Uiso 1 1 calc R . . C8 C 0.6417(6) 0.8714(5) 0.2974(4) 0.0696(17) Uani 1 1 d . . . H8 H 0.7202 0.8760 0.2993 0.084 Uiso 1 1 calc R . . C9 C 0.6060(6) 0.7725(5) 0.3273(4) 0.0657(16) Uani 1 1 d . . . H9 H 0.6621 0.7095 0.3481 0.079 Uiso 1 1 calc R . . N10 N 0.4967(4) 0.7632(3) 0.3278(3) 0.0515(11) Uani 1 1 d . . . C11 C 0.2982(5) 0.8389(4) 0.3014(3) 0.0553(14) Uani 1 1 d . . . C12 C 0.4181(5) 0.8533(4) 0.2991(4) 0.0575(14) Uani 1 1 d . . . C13 C 0.2107(6) 0.9262(5) 0.2707(4) 0.0651(17) Uani 1 1 d . . . C14 C 0.4439(6) 0.9561(5) 0.2646(4) 0.0632(15) Uani 1 1 d . . . C20 C 0.4546(4) 0.3508(4) 0.3576(3) 0.0501(12) Uani 1 1 d . . . C21 C 0.4968(5) 0.3944(4) 0.2620(3) 0.0525(13) Uani 1 1 d . . . H21 H 0.4655 0.4653 0.2260 0.063 Uiso 1 1 calc R . . C22 C 0.5850(5) 0.3326(4) 0.2207(3) 0.0517(13) Uani 1 1 d . . . C23 C 0.6315(5) 0.2292(4) 0.2734(3) 0.0510(13) Uani 1 1 d . . . H23 H 0.6919 0.1876 0.2448 0.061 Uiso 1 1 calc R . . C24 C 0.5898(5) 0.1869(4) 0.3674(4) 0.0511(13) Uani 1 1 d . . . C25 C 0.5001(4) 0.2469(4) 0.4081(3) 0.0495(12) Uani 1 1 d . . . H25 H 0.4692 0.2162 0.4718 0.059 Uiso 1 1 calc R . . O26A O 0.3057(3) 0.3714(3) 0.4783(2) 0.0557(10) Uani 1 1 d . . . O26B O 0.3466(3) 0.5184(3) 0.3645(2) 0.0543(9) Uani 1 1 d . . . C26 C 0.3635(4) 0.4177(4) 0.4048(4) 0.0493(12) Uani 1 1 d . . . O27A O 0.5895(4) 0.4743(3) 0.0747(3) 0.0693(12) Uani 1 1 d . . . H27A H 0.6243 0.4926 0.0198 0.083 Uiso 1 1 calc R . . O27B O 0.7233(4) 0.3253(3) 0.0894(3) 0.0692(12) Uani 1 1 d . . . C27 C 0.6358(5) 0.3791(4) 0.1211(3) 0.0540(14) Uani 1 1 d . . . O28A O 0.6056(3) 0.0466(3) 0.5131(2) 0.0582(10) Uani 1 1 d . . . H28A H 0.6419 -0.0146 0.5402 0.070 Uiso 1 1 calc R . . O28B O 0.7302(3) 0.0267(3) 0.3884(2) 0.0558(9) Uani 1 1 d . . . C28 C 0.6472(5) 0.0788(4) 0.4238(4) 0.0493(12) Uani 1 1 d . . . O29A O 1.0174(4) 0.3858(3) 0.0924(3) 0.0692(12) Uani 1 1 d . . . O29B O 0.8795(4) 0.5298(3) 0.0759(3) 0.0705(12) Uani 1 1 d . . . H29B H 0.9165 0.5491 0.0218 0.085 Uiso 1 1 calc R . . C30 C 0.7354(4) 0.4021(4) 0.3557(3) 0.0494(12) Uani 1 1 d . . . C31 C 0.7819(4) 0.4470(4) 0.2621(3) 0.0496(12) Uani 1 1 d . . . H31 H 0.7498 0.5176 0.2262 0.060 Uiso 1 1 calc R . . C32 C 0.8755(4) 0.3887(4) 0.2210(3) 0.0518(13) Uani 1 1 d . . . C33 C 0.9249(4) 0.2861(4) 0.2732(3) 0.0489(12) Uani 1 1 d . . . H33 H 0.9895 0.2466 0.2461 0.059 Uiso 1 1 calc R . . C34 C 0.8768(4) 0.2425(4) 0.3666(3) 0.0497(13) Uani 1 1 d . . . C35 C 0.7843(4) 0.2995(4) 0.4061(3) 0.0501(13) Uani 1 1 d . . . H35 H 0.7531 0.2677 0.4696 0.060 Uiso 1 1 calc R . . O36A O 0.5895(3) 0.4104(3) 0.4813(2) 0.0550(10) Uani 1 1 d . . . O36B O 0.5850(3) 0.5503(3) 0.3461(3) 0.0562(10) Uani 1 1 d . . . C36 C 0.6288(5) 0.4589(4) 0.3996(4) 0.0511(13) Uani 1 1 d . . . C37 C 0.9281(5) 0.4371(4) 0.1235(4) 0.0536(13) Uani 1 1 d . . . O38A O 0.8802(3) 0.0950(3) 0.5080(2) 0.0599(10) Uani 1 1 d . . . O38B O 1.0183(3) 0.0848(3) 0.3889(2) 0.0598(10) Uani 1 1 d . . . H38B H 1.0393 0.0243 0.4280 0.072 Uiso 1 1 calc R . . C38 C 0.9307(5) 0.1312(4) 0.4239(3) 0.0515(13) Uani 1 1 d . . . C40 C 1.0173(4) 0.4753(4) 0.3529(3) 0.0494(12) Uani 1 1 d . . . C41 C 1.0715(5) 0.5150(4) 0.2615(3) 0.0522(13) Uani 1 1 d . . . H41 H 1.0441 0.5858 0.2231 0.063 Uiso 1 1 calc R . . C42 C 1.1653(4) 0.4525(4) 0.2253(3) 0.0521(13) Uani 1 1 d . . . C43 C 1.2031(5) 0.3487(5) 0.2813(4) 0.0537(13) Uani 1 1 d . . . H43 H 1.2647 0.3043 0.2566 0.064 Uiso 1 1 calc R . . C44 C 1.1516(4) 0.3093(4) 0.3733(3) 0.0500(13) Uani 1 1 d . . . C45 C 1.0589(5) 0.3706(4) 0.4087(3) 0.0513(13) Uani 1 1 d . . . H45 H 1.0230 0.3421 0.4712 0.062 Uiso 1 1 calc R . . O46A O 0.8857(4) 0.6384(3) 0.3374(3) 0.0693(12) Uani 1 1 d . . . O46B O 0.8656(3) 0.5011(3) 0.4705(2) 0.0549(9) Uani 1 1 d . . . H46B H 0.8104 0.5458 0.4846 0.066 Uiso 1 1 calc R . . C46 C 0.9181(5) 0.5460(4) 0.3866(4) 0.0558(13) Uani 1 1 d . . . O47A O 1.1747(4) 0.5895(3) 0.0799(3) 0.0708(12) Uani 1 1 d . . . H47A H 1.2116 0.6080 0.0257 0.085 Uiso 1 1 calc R . . O47B O 1.3096(3) 0.4415(3) 0.0978(2) 0.0655(11) Uani 1 1 d . . . C47 C 1.2213(5) 0.4968(4) 0.1271(4) 0.0560(14) Uani 1 1 d . . . O48A O 1.1505(3) 0.1636(3) 0.5178(2) 0.0602(10) Uani 1 1 d . . . H48A H 1.1833 0.1013 0.5459 0.072 Uiso 1 1 calc R . . O48B O 1.2879(3) 0.1463(3) 0.3998(2) 0.0575(10) Uani 1 1 d . . . C48 C 1.2035(5) 0.1978(4) 0.4306(4) 0.0557(14) 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 0.0552(4) 0.0411(4) 0.0464(4) -0.0020(3) -0.0042(3) 0.0019(3) N1 0.062(3) 0.043(2) 0.042(2) 0.0013(18) -0.006(2) -0.003(2) C2 0.062(3) 0.055(3) 0.050(3) -0.005(3) -0.006(3) -0.004(3) C3 0.060(3) 0.066(4) 0.050(3) -0.005(3) -0.008(3) 0.000(3) C4 0.073(4) 0.057(4) 0.058(3) -0.016(3) -0.016(3) 0.006(3) C5 0.084(5) 0.051(3) 0.068(4) -0.009(3) -0.009(3) 0.005(3) C6 0.114(6) 0.039(3) 0.062(4) -0.014(3) -0.013(4) -0.004(3) C7 0.107(5) 0.057(4) 0.052(3) -0.006(3) -0.005(3) -0.026(4) C8 0.078(4) 0.066(4) 0.061(3) -0.009(3) -0.004(3) -0.027(3) C9 0.079(4) 0.064(4) 0.045(3) -0.004(3) -0.012(3) -0.016(3) N10 0.061(3) 0.042(2) 0.041(2) -0.0032(18) -0.0072(19) -0.006(2) C11 0.071(4) 0.043(3) 0.039(3) -0.006(2) -0.005(2) 0.001(2) C12 0.069(3) 0.046(3) 0.046(3) -0.004(2) -0.008(3) -0.003(3) C13 0.079(4) 0.049(3) 0.045(3) -0.001(2) -0.001(3) 0.005(3) C14 0.085(4) 0.054(3) 0.043(3) -0.003(2) -0.011(3) -0.015(3) C20 0.052(3) 0.050(3) 0.045(3) -0.013(2) -0.007(2) -0.007(2) C21 0.057(3) 0.050(3) 0.040(3) 0.000(2) -0.012(2) -0.010(2) C22 0.054(3) 0.052(3) 0.037(2) -0.003(2) -0.001(2) -0.008(2) C23 0.052(3) 0.052(3) 0.041(3) -0.006(2) -0.005(2) -0.010(2) C24 0.058(3) 0.047(3) 0.045(3) -0.011(2) -0.006(2) -0.007(2) C25 0.051(3) 0.048(3) 0.042(3) -0.007(2) -0.004(2) -0.009(2) O26A 0.057(2) 0.050(2) 0.0459(19) -0.0060(16) -0.0029(17) -0.0001(17) O26B 0.058(2) 0.050(2) 0.0488(19) -0.0103(17) -0.0066(16) -0.0057(16) C26 0.052(3) 0.042(3) 0.047(3) -0.006(2) -0.014(2) -0.001(2) O27A 0.078(3) 0.066(3) 0.0397(19) 0.0027(18) -0.0021(18) -0.002(2) O27B 0.076(3) 0.068(3) 0.044(2) -0.0064(19) 0.0039(19) -0.003(2) C27 0.061(3) 0.052(3) 0.035(2) -0.001(2) -0.009(2) -0.003(3) O28A 0.066(2) 0.045(2) 0.0404(18) 0.0018(15) 0.0002(16) 0.0037(17) O28B 0.065(2) 0.045(2) 0.0435(19) -0.0040(16) -0.0041(17) -0.0016(17) C28 0.057(3) 0.037(3) 0.047(3) -0.004(2) -0.011(2) -0.007(2) O29A 0.071(3) 0.061(2) 0.048(2) 0.0000(18) 0.0034(19) 0.001(2) O29B 0.079(3) 0.055(2) 0.042(2) 0.0112(17) 0.0018(18) 0.005(2) C30 0.051(3) 0.042(3) 0.045(3) -0.006(2) -0.007(2) -0.003(2) C31 0.056(3) 0.039(3) 0.042(3) 0.000(2) -0.010(2) -0.002(2) C32 0.050(3) 0.049(3) 0.042(3) 0.001(2) -0.006(2) -0.006(2) C33 0.051(3) 0.046(3) 0.041(3) -0.007(2) -0.003(2) -0.006(2) C34 0.052(3) 0.040(3) 0.043(3) 0.000(2) -0.006(2) -0.003(2) C35 0.049(3) 0.048(3) 0.041(3) -0.003(2) -0.004(2) -0.006(2) O36A 0.057(2) 0.053(2) 0.0391(18) -0.0049(16) -0.0022(16) 0.0032(17) O36B 0.056(2) 0.042(2) 0.054(2) -0.0018(16) -0.0054(17) -0.0017(16) C36 0.051(3) 0.041(3) 0.056(3) -0.010(2) -0.011(2) -0.005(2) C37 0.061(3) 0.048(3) 0.044(3) -0.007(2) -0.006(2) -0.010(3) O38A 0.060(2) 0.048(2) 0.044(2) 0.0063(16) 0.0004(17) 0.0023(17) O38B 0.069(2) 0.043(2) 0.0459(19) -0.0015(16) -0.0024(18) 0.0070(18) C38 0.061(3) 0.042(3) 0.038(3) -0.003(2) -0.002(2) -0.004(2) C40 0.052(3) 0.047(3) 0.042(3) -0.007(2) -0.006(2) -0.007(2) C41 0.058(3) 0.045(3) 0.044(3) -0.001(2) -0.015(2) -0.004(2) C42 0.052(3) 0.051(3) 0.037(2) 0.002(2) -0.009(2) -0.002(2) C43 0.048(3) 0.056(3) 0.048(3) -0.008(2) -0.009(2) -0.004(2) C44 0.050(3) 0.043(3) 0.043(3) -0.002(2) -0.007(2) -0.002(2) C45 0.063(3) 0.051(3) 0.037(2) -0.008(2) -0.008(2) -0.012(2) O46A 0.080(3) 0.042(2) 0.060(2) 0.0007(18) 0.008(2) -0.0009(18) O46B 0.056(2) 0.050(2) 0.0448(19) -0.0080(16) 0.0013(16) -0.0016(16) C46 0.061(3) 0.050(3) 0.049(3) -0.009(2) -0.008(2) -0.007(3) O47A 0.080(3) 0.062(3) 0.0388(19) 0.0061(18) 0.0059(18) 0.002(2) O47B 0.062(2) 0.066(3) 0.044(2) -0.0020(18) 0.0033(17) 0.002(2) C47 0.065(3) 0.050(3) 0.041(3) -0.002(2) -0.006(2) -0.008(3) O48A 0.065(2) 0.049(2) 0.0417(19) 0.0054(16) -0.0038(17) 0.0021(17) O48B 0.060(2) 0.047(2) 0.0457(19) -0.0032(16) -0.0009(17) 0.0066(17) C48 0.061(3) 0.048(3) 0.042(3) -0.001(2) -0.002(2) -0.006(3) _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 O36B 1.930(4) . ? Cu1 O26B 1.966(4) . ? Cu1 N10 2.021(5) . ? Cu1 N1 2.030(4) . ? Cu1 O36A 2.198(3) 2_666 ? N1 C2 1.340(7) . ? N1 C11 1.355(7) . ? C2 C3 1.393(8) . ? C3 C4 1.369(9) . ? C4 C13 1.406(9) . ? C5 C6 1.384(10) . ? C5 C13 1.439(9) . ? C6 C14 1.433(9) . ? C7 C8 1.361(10) . ? C7 C14 1.408(10) . ? C8 C9 1.394(9) . ? C9 N10 1.324(8) . ? N10 C12 1.345(7) . ? C11 C13 1.388(8) . ? C11 C12 1.465(9) . ? C12 C14 1.391(8) . ? C20 C25 1.382(7) . ? C20 C21 1.407(7) . ? C20 C26 1.502(7) . ? C21 C22 1.393(7) . ? C22 C23 1.390(7) . ? C22 C27 1.490(7) . ? C23 C24 1.383(7) . ? C24 C25 1.382(7) . ? C24 C28 1.490(7) . ? O26A C26 1.236(6) . ? O26B C26 1.270(6) . ? O27A C27 1.282(6) . ? O27B C27 1.253(6) . ? O28A C28 1.311(6) . ? O28B C28 1.236(6) . ? O29A C37 1.245(7) . ? O29B C37 1.273(6) . ? C30 C35 1.381(7) . ? C30 C31 1.398(7) . ? C30 C36 1.503(7) . ? C31 C32 1.398(7) . ? C32 C33 1.390(7) . ? C32 C37 1.476(7) . ? C33 C34 1.400(7) . ? C34 C35 1.368(7) . ? C34 C38 1.512(7) . ? O36A C36 1.242(6) . ? O36A Cu1 2.198(3) 2_666 ? O36B C36 1.272(6) . ? O38A C38 1.283(6) . ? O38B C38 1.226(6) . ? C40 C41 1.392(7) . ? C40 C45 1.402(7) . ? C40 C46 1.481(7) . ? C41 C42 1.395(8) . ? C42 C43 1.384(7) . ? C42 C47 1.489(7) . ? C43 C44 1.387(7) . ? C44 C45 1.373(7) . ? C44 C48 1.506(7) . ? O46A C46 1.226(6) . ? O46B C46 1.311(6) . ? O47A C47 1.263(6) . ? O47B C47 1.254(7) . ? O48A C48 1.328(6) . ? O48B C48 1.208(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 O36B Cu1 O26B 95.88(16) . . ? O36B Cu1 N10 89.51(17) . . ? O26B Cu1 N10 162.87(16) . . ? O36B Cu1 N1 159.43(16) . . ? O26B Cu1 N1 88.29(18) . . ? N10 Cu1 N1 81.22(19) . . ? O36B Cu1 O36A 99.95(15) . 2_666 ? O26B Cu1 O36A 97.01(15) . 2_666 ? N10 Cu1 O36A 98.05(16) . 2_666 ? N1 Cu1 O36A 99.52(15) . 2_666 ? C2 N1 C11 118.1(5) . . ? C2 N1 Cu1 128.4(4) . . ? C11 N1 Cu1 113.4(4) . . ? N1 C2 C3 121.8(6) . . ? C4 C3 C2 119.9(6) . . ? C3 C4 C13 119.4(5) . . ? C6 C5 C13 121.0(6) . . ? C5 C6 C14 120.6(6) . . ? C8 C7 C14 121.6(6) . . ? C7 C8 C9 118.4(6) . . ? N10 C9 C8 122.4(6) . . ? C9 N10 C12 118.0(5) . . ? C9 N10 Cu1 128.2(4) . . ? C12 N10 Cu1 113.8(4) . . ? N1 C11 C13 123.7(6) . . ? N1 C11 C12 115.4(5) . . ? C13 C11 C12 120.9(5) . . ? N10 C12 C14 124.8(6) . . ? N10 C12 C11 116.0(5) . . ? C14 C12 C11 119.1(5) . . ? C11 C13 C4 117.1(6) . . ? C11 C13 C5 118.6(6) . . ? C4 C13 C5 124.3(6) . . ? C12 C14 C7 114.6(6) . . ? C12 C14 C6 119.8(6) . . ? C7 C14 C6 125.6(6) . . ? C25 C20 C21 119.3(5) . . ? C25 C20 C26 120.5(4) . . ? C21 C20 C26 120.2(5) . . ? C22 C21 C20 119.2(5) . . ? C23 C22 C21 120.5(4) . . ? C23 C22 C27 119.2(5) . . ? C21 C22 C27 120.2(5) . . ? C24 C23 C22 120.0(5) . . ? C25 C24 C23 119.8(5) . . ? C25 C24 C28 121.4(4) . . ? C23 C24 C28 118.7(5) . . ? C20 C25 C24 121.2(5) . . ? C26 O26B Cu1 131.2(4) . . ? O26A C26 O26B 123.7(5) . . ? O26A C26 C20 118.1(4) . . ? O26B C26 C20 118.1(4) . . ? O27B C27 O27A 124.3(5) . . ? O27B C27 C22 118.4(4) . . ? O27A C27 C22 117.2(5) . . ? O28B C28 O28A 123.5(4) . . ? O28B C28 C24 121.6(4) . . ? O28A C28 C24 114.8(5) . . ? C35 C30 C31 118.5(5) . . ? C35 C30 C36 119.6(4) . . ? C31 C30 C36 121.8(4) . . ? C32 C31 C30 120.4(4) . . ? C33 C32 C31 120.5(4) . . ? C33 C32 C37 118.7(5) . . ? C31 C32 C37 120.7(4) . . ? C32 C33 C34 118.2(5) . . ? C35 C34 C33 121.1(4) . . ? C35 C34 C38 120.4(4) . . ? C33 C34 C38 118.4(5) . . ? C34 C35 C30 121.4(5) . . ? C36 O36A Cu1 152.9(4) . 2_666 ? C36 O36B Cu1 126.5(3) . . ? O36A C36 O36B 127.0(5) . . ? O36A C36 C30 117.4(4) . . ? O36B C36 C30 115.4(4) . . ? O29A C37 O29B 123.5(5) . . ? O29A C37 C32 118.6(5) . . ? O29B C37 C32 117.8(5) . . ? O38B C38 O38A 125.7(5) . . ? O38B C38 C34 119.1(4) . . ? O38A C38 C34 115.2(4) . . ? C41 C40 C45 118.7(5) . . ? C41 C40 C46 118.2(5) . . ? C45 C40 C46 123.1(4) . . ? C40 C41 C42 121.2(5) . . ? C43 C42 C41 119.0(4) . . ? C43 C42 C47 121.0(5) . . ? C41 C42 C47 120.0(4) . . ? C42 C43 C44 120.3(5) . . ? C45 C44 C43 120.6(5) . . ? C45 C44 C48 122.9(4) . . ? C43 C44 C48 116.5(5) . . ? C44 C45 C40 120.2(5) . . ? O46A C46 O46B 123.2(5) . . ? O46A C46 C40 121.8(5) . . ? O46B C46 C40 115.0(4) . . ? O47B C47 O47A 125.1(5) . . ? O47B C47 C42 119.0(4) . . ? O47A C47 C42 115.9(5) . . ? O48B C48 O48A 123.7(5) . . ? O48B C48 C44 122.2(4) . . ? O48A C48 C44 114.1(5) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.122 _refine_diff_density_min -0.867 _refine_diff_density_rms 0.108