Electronic Supplementary Material for CrystengComm This journal is (c) The Royal Society of Chemistry 2007 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_Compound-1 _database_code_depnum_ccdc_archive 'CCDC 649820' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 Cl Cu F N3 O7' _chemical_formula_weight 553.38 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' F F 0.0171 0.0103 '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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4640(5) _cell_length_b 11.7638(8) _cell_length_c 13.5851(9) _cell_angle_alpha 81.1320(10) _cell_angle_beta 79.1240(10) _cell_angle_gamma 73.0270(10) _cell_volume 1114.14(13) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 5109 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 30.96 _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 1.650 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 562 _exptl_absorpt_coefficient_mu 1.160 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.7158 _exptl_absorpt_correction_T_max 0.9141 _exptl_absorpt_process_details 'SHELXTL V 6.12 (Sheldrick, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX AXS CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_decay_% . _diffrn_reflns_number 9162 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0460 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3914 _reflns_number_gt 3148 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625 (Bruker, 1999)' _computing_cell_refinement 'SMART V 5.625 (Bruker, 1999)' _computing_data_reduction 'SAINT V 6.23C (Bruker, 1999)' _computing_structure_solution 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V 6.12 (Sheldrick, 2000)' _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^)+(0.0440P)^2^] 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 SHELXL _refine_ls_extinction_coef 0.0035(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3914 _refine_ls_number_parameters 370 _refine_ls_number_restraints 142 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0811 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 1.187 _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 Cu Cu 0.68347(5) -0.01716(3) 0.74215(3) 0.03990(16) Uani 1 1 d . . . O1 O 0.7106(3) 0.08224(19) 0.83428(16) 0.0433(5) Uani 1 1 d . . . O2 O 1.0124(3) 0.0594(2) 0.76962(18) 0.0611(7) Uani 1 1 d . . . O3 O 0.3712(4) 0.0845(2) 0.7599(2) 0.0604(8) Uani 1 1 d . . . H3A H 0.361(6) 0.148(4) 0.754(3) 0.072 Uiso 1 1 d . . . H3B H 0.270(6) 0.073(4) 0.772(3) 0.072 Uiso 1 1 d . . . N3 N 0.7278(4) 0.0798(3) 0.60667(19) 0.0439(7) Uani 1 1 d . . . N2 N 0.7052(4) -0.1343(2) 0.6521(2) 0.0437(7) Uani 1 1 d . . . N1 N 0.6637(3) -0.1585(2) 0.8437(2) 0.0422(6) Uani 1 1 d . . . C2 C 0.6375(5) -0.1609(3) 0.9443(2) 0.0462(8) Uani 1 1 d . . . H2 H 0.6371 -0.0932 0.9719 0.055 Uiso 1 1 calc R . . C3 C 0.6115(5) -0.2585(3) 1.0080(3) 0.0520(9) Uani 1 1 d . . . H3 H 0.5920 -0.2568 1.0775 0.062 Uiso 1 1 calc R . . C4 C 0.6148(5) -0.3592(3) 0.9672(3) 0.0617(10) Uani 1 1 d . . . H4 H 0.5989 -0.4271 1.0091 0.074 Uiso 1 1 calc R . . C5 C 0.6418(5) -0.3590(3) 0.8639(3) 0.0592(10) Uani 1 1 d . . . H5 H 0.6434 -0.4264 0.8356 0.071 Uiso 1 1 calc R . . C6 C 0.6663(4) -0.2580(3) 0.8034(3) 0.0455(8) Uani 1 1 d . . . C7 C 0.6954(5) -0.2443(3) 0.6921(3) 0.0493(9) Uani 1 1 d . . . C8 C 0.7110(6) -0.3300(4) 0.6294(3) 0.0682(11) Uani 1 1 d . . . H8 H 0.7044 -0.4066 0.6561 0.082 Uiso 1 1 calc R . . C9 C 0.7361(6) -0.3000(4) 0.5276(3) 0.0740(13) Uani 1 1 d . . . H9 H 0.7444 -0.3564 0.4847 0.089 Uiso 1 1 calc R . . C10 C 0.7496(5) -0.1872(4) 0.4872(3) 0.0667(12) Uani 1 1 d . . . H10 H 0.7686 -0.1676 0.4178 0.080 Uiso 1 1 calc R . . C11 C 0.7342(5) -0.1038(3) 0.5521(3) 0.0502(9) Uani 1 1 d . . . C12 C 0.7449(4) 0.0209(3) 0.5258(2) 0.0465(8) Uani 1 1 d . . . C13 C 0.7716(5) 0.0752(4) 0.4293(3) 0.0615(11) Uani 1 1 d . . . H13 H 0.7868 0.0329 0.3744 0.074 Uiso 1 1 calc R . . C14 C 0.7756(5) 0.1922(4) 0.4146(3) 0.0694(12) Uani 1 1 d . . . H14 H 0.7929 0.2301 0.3496 0.083 Uiso 1 1 calc R . . C15 C 0.7540(5) 0.2532(4) 0.4959(3) 0.0641(11) Uani 1 1 d . . . H15 H 0.7543 0.3331 0.4871 0.077 Uiso 1 1 calc R . . C16 C 0.7320(5) 0.1939(3) 0.5907(3) 0.0536(9) Uani 1 1 d . . . H16 H 0.7196 0.2349 0.6460 0.064 Uiso 1 1 calc R . . C17 C 0.8817(4) 0.1786(3) 0.9051(3) 0.0404(8) Uani 1 1 d . A . C19 C 0.8524(5) 0.2202(4) 1.0768(3) 0.0687(12) Uani 1 1 d . A . H19 H 0.8280 0.1979 1.1456 0.082 Uiso 1 1 calc R . . C20 C 0.9004(6) 0.3249(5) 1.0425(4) 0.0808(16) Uani 1 1 d . . . H20 H 0.9056 0.3746 1.0883 0.097 Uiso 1 1 calc R . . C21 C 0.9407(6) 0.3566(4) 0.9415(4) 0.0771(14) Uani 1 1 d . A . H21 H 0.9729 0.4279 0.9189 0.093 Uiso 1 1 calc R . . C23 C 0.8714(5) 0.1003(3) 0.8302(2) 0.0393(7) Uani 1 1 d . . . C18 C 0.8406(4) 0.1478(3) 1.0085(2) 0.0491(9) Uani 1 1 d DU . . F1 F 0.7868(4) 0.0496(2) 1.03915(18) 0.0600(10) Uani 0.743(5) 1 d PDU A 1 H18 H 0.7937 0.0830 1.0380 0.072 Uiso 0.257(5) 1 d PRD A 2 C22 C 0.9339(5) 0.2834(3) 0.8727(3) 0.0576(10) Uani 1 1 d DU . . H22 H 0.9307 0.3192 0.8034 0.069 Uiso 0.743(5) 1 d PRD A 1 F1A F 0.9451(14) 0.3098(8) 0.7699(7) 0.087(3) Uani 0.257(5) 1 d PDU A 2 Cl Cl 0.65801(18) 0.54727(9) 0.28811(7) 0.0701(3) Uani 1 1 d DU . . O4 O 0.690(2) 0.6596(7) 0.2877(9) 0.096(3) Uani 0.638(12) 1 d PDU B 1 O5 O 0.5791(14) 0.5172(12) 0.3872(6) 0.107(3) Uani 0.638(12) 1 d PDU B 1 O6 O 0.8265(15) 0.4578(7) 0.2612(8) 0.149(3) Uani 0.638(12) 1 d PDU B 1 O7 O 0.5272(19) 0.5612(10) 0.2224(7) 0.156(4) Uani 0.638(12) 1 d PDU B 1 O4A O 0.650(4) 0.6647(13) 0.2545(16) 0.109(5) Uani 0.362(12) 1 d PDU B 2 O5A O 0.510(3) 0.533(2) 0.3653(14) 0.123(6) Uani 0.362(12) 1 d PDU B 2 O6A O 0.832(2) 0.4911(16) 0.3259(16) 0.148(5) Uani 0.362(12) 1 d PDU B 2 O7A O 0.649(3) 0.4898(16) 0.2122(10) 0.138(5) Uani 0.362(12) 1 d PDU B 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 Cu 0.0410(3) 0.0457(3) 0.0368(2) -0.01289(18) -0.00591(17) -0.01317(18) O1 0.0402(12) 0.0542(14) 0.0427(13) -0.0178(11) -0.0035(10) -0.0191(11) O2 0.0394(14) 0.094(2) 0.0561(15) -0.0429(15) 0.0007(12) -0.0151(13) O3 0.0355(13) 0.0545(17) 0.092(2) -0.0114(16) -0.0084(14) -0.0123(14) N3 0.0376(15) 0.0565(19) 0.0380(15) -0.0091(13) -0.0046(12) -0.0117(13) N2 0.0417(16) 0.0503(18) 0.0424(16) -0.0156(14) -0.0116(13) -0.0088(13) N1 0.0366(15) 0.0416(16) 0.0488(17) -0.0110(13) -0.0088(13) -0.0067(12) C2 0.0426(19) 0.051(2) 0.044(2) -0.0098(17) -0.0092(16) -0.0068(16) C3 0.045(2) 0.055(2) 0.050(2) -0.0014(18) -0.0075(17) -0.0059(17) C4 0.051(2) 0.053(2) 0.076(3) 0.005(2) -0.011(2) -0.0114(18) C5 0.058(2) 0.044(2) 0.079(3) -0.011(2) -0.017(2) -0.0125(18) C6 0.0390(18) 0.042(2) 0.058(2) -0.0124(17) -0.0138(16) -0.0065(15) C7 0.043(2) 0.050(2) 0.060(2) -0.0193(18) -0.0149(17) -0.0084(16) C8 0.075(3) 0.058(3) 0.082(3) -0.030(2) -0.028(2) -0.013(2) C9 0.086(3) 0.074(3) 0.073(3) -0.043(3) -0.024(2) -0.011(2) C10 0.066(3) 0.085(3) 0.053(2) -0.033(2) -0.017(2) -0.007(2) C11 0.0384(19) 0.067(3) 0.045(2) -0.0209(18) -0.0112(16) -0.0029(17) C12 0.0347(18) 0.064(2) 0.039(2) -0.0143(17) -0.0064(15) -0.0061(16) C13 0.055(2) 0.083(3) 0.038(2) -0.014(2) -0.0055(18) -0.003(2) C14 0.060(3) 0.093(3) 0.045(2) 0.007(2) -0.006(2) -0.013(2) C15 0.064(3) 0.067(3) 0.057(3) 0.004(2) -0.007(2) -0.017(2) C16 0.054(2) 0.059(2) 0.048(2) -0.0064(18) -0.0075(18) -0.0167(18) C17 0.0294(16) 0.0423(19) 0.051(2) -0.0162(16) -0.0088(15) -0.0052(14) C19 0.047(2) 0.100(4) 0.061(3) -0.043(2) -0.0152(19) 0.000(2) C20 0.050(2) 0.085(4) 0.119(4) -0.070(3) -0.024(3) 0.000(2) C21 0.054(3) 0.051(3) 0.135(4) -0.037(3) -0.023(3) -0.0090(19) C23 0.0415(19) 0.0420(19) 0.0364(18) -0.0059(15) -0.0103(16) -0.0108(15) C18 0.0372(19) 0.059(2) 0.052(2) -0.0205(18) -0.0085(16) -0.0063(17) F1 0.0631(19) 0.074(2) 0.0447(16) -0.0015(14) -0.0080(13) -0.0239(15) C22 0.052(2) 0.048(2) 0.077(3) -0.014(2) -0.016(2) -0.0109(18) F1A 0.105(7) 0.068(6) 0.092(5) 0.007(5) -0.007(6) -0.043(5) Cl 0.1145(9) 0.0535(6) 0.0464(6) -0.0064(5) -0.0042(6) -0.0337(6) O4 0.132(6) 0.066(3) 0.103(7) -0.014(4) -0.005(5) -0.050(4) O5 0.159(7) 0.089(5) 0.057(3) 0.017(3) 0.000(3) -0.032(5) O6 0.189(6) 0.096(4) 0.119(7) -0.039(4) 0.018(5) 0.018(4) O7 0.244(9) 0.147(8) 0.128(6) 0.019(5) -0.109(6) -0.098(6) O4A 0.164(12) 0.066(5) 0.089(11) 0.025(5) 0.000(8) -0.046(6) O5A 0.157(9) 0.094(10) 0.111(10) -0.011(8) 0.052(8) -0.066(9) O6A 0.136(7) 0.138(10) 0.162(12) 0.023(9) -0.064(8) -0.018(7) O7A 0.191(11) 0.139(9) 0.096(7) -0.075(7) -0.015(7) -0.038(9) _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 Cu O1 1.913(2) . ? Cu N2 1.933(3) . ? Cu N1 2.012(3) . ? Cu N3 2.035(3) . ? Cu O3 2.274(3) . ? Cu O2 2.952(2) . ? O1 C23 1.268(4) . ? O2 C23 1.231(4) . ? O3 H3A 0.72(4) . ? O3 H3B 0.79(4) . ? N3 C16 1.335(4) . ? N3 C12 1.354(4) . ? N2 C7 1.341(4) . ? N2 C11 1.343(4) . ? N1 C2 1.340(4) . ? N1 C6 1.360(4) . ? C2 C3 1.365(5) . ? C2 H2 0.9300 . ? C3 C4 1.375(5) . ? C3 H3 0.9300 . ? C4 C5 1.379(5) . ? C4 H4 0.9300 . ? C5 C6 1.375(5) . ? C5 H5 0.9300 . ? C6 C7 1.477(5) . ? C7 C8 1.383(5) . ? C8 C9 1.365(6) . ? C8 H8 0.9300 . ? C9 C10 1.379(6) . ? C9 H9 0.9300 . ? C10 C11 1.384(5) . ? C10 H10 0.9300 . ? C11 C12 1.477(5) . ? C12 C13 1.373(5) . ? C13 C14 1.369(6) . ? C13 H13 0.9300 . ? C14 C15 1.367(5) . ? C14 H14 0.9300 . ? C15 C16 1.371(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C22 1.383(5) . ? C17 C18 1.395(4) . ? C17 C23 1.499(4) . ? C19 C20 1.372(6) . ? C19 C18 1.382(5) . ? C19 H19 0.9300 . ? C20 C21 1.365(7) . ? C20 H20 0.9300 . ? C21 C22 1.383(5) . ? C21 H21 0.9300 . ? C18 F1 1.3153(14) . ? C18 H18 0.9340 . ? C22 F1A 1.374(10) . ? C22 H22 0.9719 . ? Cl O7A 1.339(10) . ? Cl O4A 1.374(12) . ? Cl O5A 1.399(12) . ? Cl O5 1.400(7) . ? Cl O7 1.403(7) . ? Cl O4 1.408(7) . ? Cl O6 1.413(7) . ? Cl O6A 1.425(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 O1 Cu N2 169.05(10) . . ? O1 Cu N1 96.72(10) . . ? N2 Cu N1 80.27(11) . . ? O1 Cu N3 102.25(10) . . ? N2 Cu N3 79.79(11) . . ? N1 Cu N3 159.78(11) . . ? O1 Cu O3 86.91(10) . . ? N2 Cu O3 103.91(10) . . ? N1 Cu O3 98.21(10) . . ? N3 Cu O3 89.79(11) . . ? O1 Cu O2 48.48(7) . . ? N2 Cu O2 122.30(9) . . ? N1 Cu O2 108.16(9) . . ? N3 Cu O2 80.05(9) . . ? O3 Cu O2 129.41(8) . . ? C23 O1 Cu 118.5(2) . . ? C23 O2 Cu 68.62(17) . . ? Cu O3 H3A 110(4) . . ? Cu O3 H3B 141(3) . . ? H3A O3 H3B 109(5) . . ? C16 N3 C12 118.4(3) . . ? C16 N3 Cu 127.1(2) . . ? C12 N3 Cu 114.5(2) . . ? C7 N2 C11 122.4(3) . . ? C7 N2 Cu 118.5(2) . . ? C11 N2 Cu 119.0(2) . . ? C2 N1 C6 118.6(3) . . ? C2 N1 Cu 126.7(2) . . ? C6 N1 Cu 114.6(2) . . ? N1 C2 C3 122.8(3) . . ? N1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C2 C3 C4 118.6(3) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C3 C4 C5 119.6(4) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 119.3(3) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? N1 C6 C5 121.1(3) . . ? N1 C6 C7 113.5(3) . . ? C5 C6 C7 125.3(3) . . ? N2 C7 C8 119.7(4) . . ? N2 C7 C6 112.9(3) . . ? C8 C7 C6 127.3(4) . . ? C9 C8 C7 118.8(4) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C10 121.0(4) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 C11 118.7(4) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? N2 C11 C10 119.3(4) . . ? N2 C11 C12 112.8(3) . . ? C10 C11 C12 127.8(4) . . ? N3 C12 C13 121.3(4) . . ? N3 C12 C11 113.9(3) . . ? C13 C12 C11 124.8(3) . . ? C14 C13 C12 119.3(4) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C15 C14 C13 119.8(4) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 118.6(4) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? N3 C16 C15 122.6(4) . . ? N3 C16 H16 118.7 . . ? C15 C16 H16 118.7 . . ? C22 C17 C18 118.3(3) . . ? C22 C17 C23 120.4(3) . . ? C18 C17 C23 121.3(3) . . ? C20 C19 C18 119.7(4) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C21 C20 C19 120.4(4) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 120.4(4) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? O2 C23 O1 124.4(3) . . ? O2 C23 C17 120.2(3) . . ? O1 C23 C17 115.4(3) . . ? F1 C18 C19 121.0(3) . . ? F1 C18 C17 118.2(3) . . ? C19 C18 C17 120.7(3) . . ? C19 C18 H18 114.0 . . ? C17 C18 H18 125.0 . . ? F1A C22 C21 127.2(6) . . ? F1A C22 C17 111.6(5) . . ? C21 C22 C17 120.5(4) . . ? C21 C22 H22 116.4 . . ? C17 C22 H22 120.8 . . ? O5 Cl O7 110.2(6) . . ? O5 Cl O4 105.6(8) . . ? O7 Cl O4 107.6(5) . . ? O5 Cl O6 109.1(6) . . ? O7 Cl O6 111.4(5) . . ? O4 Cl O6 112.8(7) . . ? O7A Cl O6A 108.9(9) . . ? O4A Cl O6A 109.5(11) . . ? O5A Cl O6A 107.6(10) . . ? O7A Cl O4A 110.0(10) . . ? O7A Cl O5A 107.5(12) . . ? O4A Cl O5A 113.3(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3B O2 0.79(4) 1.98(4) 2.756(3) 167(4) 1_455 O3 H3A O4 0.72(4) 2.19(4) 2.898(8) 170(5) 2_666 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.360 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.057 data_Compound-2 _database_code_depnum_ccdc_archive 'CCDC 649821' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 Cl Cu F N3 O7' _chemical_formula_weight 553.38 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' F F 0.0171 0.0103 '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 'P 21/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 8.4714(7) _cell_length_b 20.2757(17) _cell_length_c 13.3148(11) _cell_angle_alpha 90.00 _cell_angle_beta 100.051(2) _cell_angle_gamma 90.00 _cell_volume 2251.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 3850 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 30.89 _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1124 _exptl_absorpt_coefficient_mu 1.147 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.6964 _exptl_absorpt_correction_T_max 0.9038 _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX AXS CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 0.65 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% . _diffrn_reflns_number 18210 _diffrn_reflns_av_R_equivalents 0.0869 _diffrn_reflns_av_sigmaI/netI 0.1210 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3963 _reflns_number_gt 2046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625' _computing_cell_refinement 'SMART V 5.625' _computing_data_reduction 'SAINTPLUS V 7.01' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V 6.10' _computing_publication_material 'SHELXTL V 6.10' _exptl_absorpt_process_details 'Shelxtl v 6.10' _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^)+(0.0400P)^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 3963 _refine_ls_number_parameters 335 _refine_ls_number_restraints 192 _refine_ls_R_factor_all 0.1111 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1146 _refine_ls_goodness_of_fit_ref 0.946 _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 Cu Cu 0.30240(9) 0.23090(4) 0.12695(6) 0.0392(3) Uani 1 1 d . . . O1 O 0.2823(5) 0.32213(19) 0.0958(3) 0.0490(12) Uani 1 1 d . . . O2 O 0.1029(6) 0.3037(2) -0.0417(3) 0.0580(13) Uani 1 1 d . . . O3 O 0.4528(6) 0.2583(2) 0.2814(4) 0.0585(16) Uani 1 1 d . . . H3A H 0.497(8) 0.238(3) 0.328(5) 0.070 Uiso 1 1 d . . . H3B H 0.468(9) 0.294(3) 0.278(6) 0.070 Uiso 1 1 d . . . F1 F 0.2179(6) 0.61035(19) -0.0672(3) 0.0954(15) Uani 1 1 d . . . N1 N 0.4961(6) 0.2107(3) 0.0614(4) 0.0418(14) Uani 1 1 d . . . N2 N 0.3115(6) 0.1364(2) 0.1425(3) 0.0349(12) Uani 1 1 d . . . N3 N 0.1019(6) 0.2160(3) 0.1872(4) 0.0417(14) Uani 1 1 d . . . C2 C 0.1997(7) 0.4133(3) -0.0077(4) 0.0394(16) Uani 1 1 d . . . C3 C 0.0992(8) 0.4405(3) -0.0905(5) 0.0511(18) Uani 1 1 d . . . H3 H 0.0254 0.4141 -0.1323 0.061 Uiso 1 1 calc R . . C4 C 0.1092(9) 0.5069(4) -0.1109(5) 0.064(2) Uani 1 1 d . . . H4 H 0.0444 0.5251 -0.1677 0.077 Uiso 1 1 calc R . . C5 C 0.2119(9) 0.5449(3) -0.0490(6) 0.060(2) Uani 1 1 d . . . C6 C 0.3145(9) 0.5195(3) 0.0327(6) 0.063(2) Uani 1 1 d . . . H6 H 0.3882 0.5465 0.0733 0.076 Uiso 1 1 calc R . . C7 C 0.3069(7) 0.4539(3) 0.0534(5) 0.0524(18) Uani 1 1 d . . . H7 H 0.3747 0.4363 0.1095 0.063 Uiso 1 1 calc R . . C8 C 0.1919(8) 0.3405(3) 0.0151(5) 0.0395(16) Uani 1 1 d . . . C9 C 0.5841(8) 0.2549(3) 0.0225(5) 0.0536(19) Uani 1 1 d . . . H9 H 0.5540 0.2990 0.0207 0.064 Uiso 1 1 calc R . . C10 C 0.7200(8) 0.2366(4) -0.0157(5) 0.062(2) Uani 1 1 d . . . H10 H 0.7798 0.2680 -0.0436 0.075 Uiso 1 1 calc R . . C11 C 0.7646(8) 0.1717(4) -0.0115(5) 0.063(2) Uani 1 1 d . . . H11 H 0.8555 0.1587 -0.0366 0.076 Uiso 1 1 calc R . . C12 C 0.6745(8) 0.1256(4) 0.0298(5) 0.0532(19) Uani 1 1 d . . . H12 H 0.7037 0.0814 0.0335 0.064 Uiso 1 1 calc R . . C13 C 0.5404(7) 0.1470(3) 0.0655(4) 0.0393(16) Uani 1 1 d . . . C14 C 0.4315(7) 0.1036(3) 0.1116(4) 0.0346(15) Uani 1 1 d . . . C15 C 0.4405(8) 0.0363(3) 0.1215(5) 0.0471(18) Uani 1 1 d . . . H15 H 0.5247 0.0129 0.1020 0.057 Uiso 1 1 calc R . . C16 C 0.3218(9) 0.0039(3) 0.1611(4) 0.0511(19) Uani 1 1 d . . . H16 H 0.3265 -0.0417 0.1682 0.061 Uiso 1 1 calc R . . C17 C 0.1963(8) 0.0379(3) 0.1903(4) 0.0437(17) Uani 1 1 d . . . H17 H 0.1151 0.0158 0.2153 0.052 Uiso 1 1 calc R . . C18 C 0.1950(7) 0.1059(3) 0.1811(4) 0.0376(16) Uani 1 1 d . . . C19 C 0.0749(7) 0.1523(3) 0.2083(5) 0.0387(16) Uani 1 1 d . . . C20 C -0.0546(8) 0.1349(3) 0.2513(5) 0.0498(18) Uani 1 1 d . . . H20 H -0.0728 0.0909 0.2653 0.060 Uiso 1 1 calc R . . C21 C -0.1562(8) 0.1824(4) 0.2733(5) 0.059(2) Uani 1 1 d . . . H21 H -0.2451 0.1709 0.3018 0.070 Uiso 1 1 calc R . . C22 C -0.1284(8) 0.2466(4) 0.2537(5) 0.061(2) Uani 1 1 d . . . H22 H -0.1960 0.2796 0.2697 0.074 Uiso 1 1 calc R . . C23 C 0.0023(7) 0.2616(3) 0.2096(5) 0.0519(18) Uani 1 1 d . . . H23 H 0.0212 0.3055 0.1950 0.062 Uiso 1 1 calc R . . Cl Cl 0.3293(2) 0.58078(9) 0.64912(14) 0.0695(6) Uani 1 1 d DU . . O4 O 0.1706(7) 0.5958(4) 0.6633(6) 0.0970(18) Uani 0.562(5) 1 d PDU A 1 O5 O 0.4303(10) 0.5855(5) 0.7425(5) 0.0931(14) Uani 0.562(5) 1 d PDU A 1 O6 O 0.3276(9) 0.5167(3) 0.6107(7) 0.0899(16) Uani 0.562(5) 1 d PDU A 1 O7 O 0.3670(9) 0.6251(4) 0.5759(6) 0.0951(17) Uani 0.562(5) 1 d PDU A 1 O4A O 0.1776(8) 0.6105(5) 0.6293(8) 0.0970(18) Uani 0.438(5) 1 d PDU A 2 O5A O 0.3877(11) 0.5689(7) 0.5573(5) 0.0931(14) Uani 0.438(5) 1 d PDU A 2 O6A O 0.4407(10) 0.6197(4) 0.7153(7) 0.0899(16) Uani 0.438(5) 1 d PDU A 2 O7A O 0.3218(12) 0.5170(4) 0.6912(10) 0.0951(17) Uani 0.438(5) 1 d PDU 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 Cu 0.0351(4) 0.0375(5) 0.0451(5) 0.0031(4) 0.0068(3) 0.0019(4) O1 0.052(3) 0.040(3) 0.051(3) 0.009(2) -0.005(2) 0.005(2) O2 0.074(4) 0.042(3) 0.053(3) -0.005(2) -0.004(3) -0.009(3) O3 0.064(3) 0.054(4) 0.049(3) 0.000(3) -0.011(2) -0.002(3) F1 0.151(4) 0.036(3) 0.096(3) 0.009(2) 0.014(3) 0.001(3) N1 0.037(3) 0.053(4) 0.036(3) -0.002(3) 0.009(3) -0.007(3) N2 0.035(3) 0.038(3) 0.029(3) 0.000(2) 0.001(2) 0.002(3) N3 0.034(3) 0.041(4) 0.050(3) -0.002(3) 0.005(3) -0.002(3) C2 0.045(4) 0.038(4) 0.035(4) -0.003(3) 0.007(3) 0.002(3) C3 0.073(5) 0.038(4) 0.038(4) -0.006(3) -0.004(4) 0.002(4) C4 0.086(6) 0.051(5) 0.047(5) 0.013(4) -0.009(4) 0.004(4) C5 0.084(6) 0.038(5) 0.058(5) 0.005(4) 0.015(5) 0.003(4) C6 0.071(5) 0.043(5) 0.070(6) -0.005(4) -0.002(4) -0.012(4) C7 0.049(4) 0.047(5) 0.058(5) 0.003(4) 0.001(4) -0.003(4) C8 0.043(4) 0.041(4) 0.037(4) -0.001(3) 0.014(3) 0.002(3) C9 0.053(5) 0.066(5) 0.043(4) 0.003(4) 0.013(4) -0.003(4) C10 0.052(5) 0.082(6) 0.057(5) -0.002(4) 0.020(4) -0.012(5) C11 0.044(5) 0.094(7) 0.055(5) -0.015(5) 0.016(4) 0.001(5) C12 0.046(5) 0.063(5) 0.051(5) -0.010(4) 0.009(4) 0.009(4) C13 0.030(4) 0.047(5) 0.039(4) -0.007(3) 0.001(3) 0.005(3) C14 0.032(4) 0.042(4) 0.027(4) -0.007(3) -0.002(3) 0.006(3) C15 0.052(5) 0.039(4) 0.046(4) -0.004(3) -0.002(3) 0.012(4) C16 0.073(5) 0.028(4) 0.049(5) -0.003(3) 0.000(4) 0.003(4) C17 0.046(4) 0.042(4) 0.042(4) 0.001(3) 0.005(3) -0.009(4) C18 0.040(4) 0.039(4) 0.031(4) 0.004(3) -0.002(3) -0.005(3) C19 0.028(4) 0.044(4) 0.042(4) -0.001(3) 0.004(3) -0.001(3) C20 0.044(4) 0.058(5) 0.047(5) 0.003(4) 0.008(4) -0.004(4) C21 0.032(4) 0.095(7) 0.054(5) 0.001(5) 0.021(4) 0.000(5) C22 0.052(5) 0.070(6) 0.065(5) -0.011(4) 0.017(4) 0.020(4) C23 0.040(4) 0.047(4) 0.070(5) -0.004(4) 0.012(4) 0.008(4) Cl 0.0712(12) 0.0531(11) 0.0750(14) -0.0029(10) -0.0123(10) -0.0103(11) O4 0.083(2) 0.085(4) 0.114(5) 0.009(3) -0.009(2) 0.009(3) O5 0.097(3) 0.091(4) 0.080(2) -0.004(2) -0.0161(18) 0.005(3) O6 0.099(3) 0.050(2) 0.104(3) -0.004(2) -0.029(3) -0.008(3) O7 0.102(4) 0.062(3) 0.110(4) 0.018(3) -0.014(3) -0.020(3) O4A 0.083(2) 0.085(4) 0.114(5) 0.009(3) -0.009(2) 0.009(3) O5A 0.097(3) 0.091(4) 0.080(2) -0.004(2) -0.0161(18) 0.005(3) O6A 0.099(3) 0.050(2) 0.104(3) -0.004(2) -0.029(3) -0.008(3) O7A 0.102(4) 0.062(3) 0.110(4) 0.018(3) -0.014(3) -0.020(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 Cu O1 1.897(4) . ? Cu N2 1.927(4) . ? Cu N3 2.023(5) . ? Cu N1 2.030(5) . ? Cu O3 2.290(5) . ? O1 C8 1.262(7) . ? O2 C8 1.224(7) . ? O3 H3A 0.79(6) . ? O3 H3B 0.74(6) . ? F1 C5 1.352(7) . ? N1 C9 1.327(7) . ? N1 C13 1.344(7) . ? N2 C14 1.339(6) . ? N2 C18 1.340(7) . ? N3 C23 1.321(7) . ? N3 C19 1.350(7) . ? C2 C7 1.382(8) . ? C2 C3 1.385(8) . ? C2 C8 1.510(8) . ? C3 C4 1.379(8) . ? C3 H3 0.9300 . ? C4 C5 1.334(9) . ? C4 H4 0.9300 . ? C5 C6 1.369(9) . ? C6 C7 1.362(8) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 C10 1.387(8) . ? C9 H9 0.9300 . ? C10 C11 1.367(9) . ? C10 H10 0.9300 . ? C11 C12 1.380(8) . ? C11 H11 0.9300 . ? C12 C13 1.376(7) . ? C12 H12 0.9300 . ? C13 C14 1.483(8) . ? C14 C15 1.373(7) . ? C15 C16 1.380(8) . ? C15 H15 0.9300 . ? C16 C17 1.379(8) . ? C16 H16 0.9300 . ? C17 C18 1.383(8) . ? C17 H17 0.9300 . ? C18 C19 1.477(8) . ? C19 C20 1.369(8) . ? C20 C21 1.357(8) . ? C20 H20 0.9300 . ? C21 C22 1.356(9) . ? C21 H21 0.9300 . ? C22 C23 1.375(8) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? Cl O5 1.384(5) . ? Cl O6 1.396(5) . ? Cl O4A 1.402(6) . ? Cl O7 1.403(5) . ? Cl O6A 1.414(6) . ? Cl O7A 1.415(6) . ? Cl O5A 1.417(6) . ? Cl O4 1.423(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 O1 Cu N2 173.39(19) . . ? O1 Cu N3 100.5(2) . . ? N2 Cu N3 80.2(2) . . ? O1 Cu N1 98.7(2) . . ? N2 Cu N1 80.0(2) . . ? N3 Cu N1 159.7(2) . . ? O1 Cu O3 88.55(17) . . ? N2 Cu O3 97.99(17) . . ? N3 Cu O3 93.09(19) . . ? N1 Cu O3 94.04(19) . . ? C8 O1 Cu 119.5(4) . . ? Cu O3 H3A 134(5) . . ? Cu O3 H3B 105(6) . . ? H3A O3 H3B 121(8) . . ? C9 N1 C13 119.5(6) . . ? C9 N1 Cu 125.7(5) . . ? C13 N1 Cu 114.6(4) . . ? C14 N2 C18 122.5(5) . . ? C14 N2 Cu 118.6(4) . . ? C18 N2 Cu 118.8(4) . . ? C23 N3 C19 119.0(6) . . ? C23 N3 Cu 126.8(5) . . ? C19 N3 Cu 114.2(4) . . ? C7 C2 C3 118.7(6) . . ? C7 C2 C8 120.8(6) . . ? C3 C2 C8 120.5(6) . . ? C4 C3 C2 119.7(6) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 119.9(7) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 F1 119.8(7) . . ? C4 C5 C6 121.9(7) . . ? F1 C5 C6 118.3(7) . . ? C7 C6 C5 118.9(7) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C7 C2 120.8(6) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? O2 C8 O1 124.2(6) . . ? O2 C8 C2 121.0(6) . . ? O1 C8 C2 114.8(6) . . ? N1 C9 C10 121.5(7) . . ? N1 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C11 C10 C9 118.9(7) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C10 C11 C12 120.0(7) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 118.2(7) . . ? C13 C12 H12 120.9 . . ? C11 C12 H12 120.9 . . ? N1 C13 C12 122.0(6) . . ? N1 C13 C14 113.4(5) . . ? C12 C13 C14 124.6(6) . . ? N2 C14 C15 119.8(6) . . ? N2 C14 C13 113.2(5) . . ? C15 C14 C13 127.0(6) . . ? C14 C15 C16 118.5(6) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C17 C16 C15 121.3(6) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C18 117.9(6) . . ? C16 C17 H17 121.1 . . ? C18 C17 H17 121.1 . . ? N2 C18 C17 120.0(6) . . ? N2 C18 C19 112.6(6) . . ? C17 C18 C19 127.5(6) . . ? N3 C19 C20 120.7(6) . . ? N3 C19 C18 114.2(6) . . ? C20 C19 C18 125.1(6) . . ? C21 C20 C19 119.5(7) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C22 C21 C20 120.1(7) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 118.3(6) . . ? C21 C22 H22 120.8 . . ? C23 C22 H22 120.8 . . ? N3 C23 C22 122.4(6) . . ? N3 C23 H23 118.8 . . ? C22 C23 H23 118.8 . . ? O5 Cl O6 111.0(3) . . ? O5 Cl O4A 122.8(6) . . ? O6 Cl O4A 112.4(6) . . ? O5 Cl O7 113.6(6) . . ? O6 Cl O7 109.3(3) . . ? O4A Cl O7 84.6(5) . . ? O5 Cl O6A 32.9(5) . . ? O6 Cl O6A 135.3(5) . . ? O4A Cl O6A 111.6(3) . . ? O7 Cl O6A 82.4(5) . . ? O5 Cl O7A 76.8(5) . . ? O6 Cl O7A 45.2(5) . . ? O4A Cl O7A 111.3(3) . . ? O7 Cl O7A 153.1(6) . . ? O6A Cl O7A 109.5(3) . . ? O5 Cl O5A 122.2(6) . . ? O6 Cl O5A 60.6(5) . . ? O4A Cl O5A 110.9(3) . . ? O7 Cl O5A 49.7(5) . . ? O6A Cl O5A 109.7(3) . . ? O7A Cl O5A 103.5(7) . . ? O5 Cl O4 108.4(3) . . ? O6 Cl O4 107.4(3) . . ? O4A Cl O4 22.6(5) . . ? O7 Cl O4 106.9(3) . . ? O6A Cl O4 109.9(6) . . ? O7A Cl O4 92.0(6) . . ? O5A Cl O4 129.1(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3A O2 0.79(6) 1.99(6) 2.775(6) 172(7) 4_666 O3 H3B O6A 0.74(6) 1.91(7) 2.632(9) 166(8) 3_666 O3 H3B O5 0.74(6) 2.62(7) 3.351(11) 170(8) 3_666 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.755 _refine_diff_density_min -0.715 _refine_diff_density_rms 0.074 data_Compound-3 _database_code_depnum_ccdc_archive 'CCDC 649822' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [aqua(4,5-dichlorophthalato-O)(2,2':6',2"-terpyridine-N,N'N")copper(II)] three hydrate ; _chemical_name_common ; (aqua(4,5-dichlorophthalato-O)(2,2':6',2''-terpyridine- N,N'N'')copper(ii)) three hydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C23 H15 Cl2 Cu N3 O5, 3(H2 O)' _chemical_formula_sum 'C23 H21 Cl2 Cu N3 O8' _chemical_formula_weight 601.87 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3590(10) _cell_length_b 12.3480(10) _cell_length_c 13.870(2) _cell_angle_alpha 87.080(10) _cell_angle_beta 81.660(10) _cell_angle_gamma 78.550(10) _cell_volume 1221.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 5.00 _cell_measurement_theta_max 12.50 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 614 _exptl_absorpt_coefficient_mu 1.167 _exptl_absorpt_correction_type Psi-scan _exptl_absorpt_correction_T_min 0.5626 _exptl_absorpt_correction_T_max 0.8256 _exptl_absorpt_process_details 'XSCANS ver 2.1 1993' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Siemens P4/PC diffractometer' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 4327 _diffrn_reflns_av_R_equivalents 0.0644 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3998 _reflns_number_gt 3243 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS ver 2.1 1993' _computing_cell_refinement 'XSCANS ver 2.1 1993' _computing_data_reduction 'XSCANS ver 2.1 1993' _computing_structure_solution 'SHELXTL V 6.10 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL V 6.10 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL V 6.10 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V 6.10 (Sheldrick, 2000)' _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^)+(0.0424P)^2^+0.5649P] 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 SHELXL _refine_ls_extinction_coef 0.0176(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3998 _refine_ls_number_parameters 359 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0922 _refine_ls_wR_factor_gt 0.0847 _refine_ls_goodness_of_fit_ref 1.033 _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 Cu Cu 0.43025(5) 0.48844(3) 0.77056(3) 0.02659(14) Uani 1 1 d . . . Cl1 Cl 1.23724(15) 0.10639(10) 0.35306(7) 0.0585(3) Uani 1 1 d . . . Cl2 Cl 1.08628(13) 0.36665(9) 0.33479(6) 0.0449(2) Uani 1 1 d . . . O1 O 0.6199(3) 0.3915(2) 0.68705(16) 0.0332(5) Uani 1 1 d . . . O2 O 0.8667(3) 0.3908(2) 0.76326(16) 0.0366(6) Uani 1 1 d . . . O3 O 0.2437(3) 0.3946(2) 0.7132(2) 0.0453(6) Uani 1 1 d D . . H3A H 0.130(3) 0.395(4) 0.726(4) 0.068 Uiso 1 1 d D . . H3B H 0.303(5) 0.328(2) 0.713(4) 0.068 Uiso 1 1 d D . . O4 O 0.8016(4) 0.1389(2) 0.7661(2) 0.0495(7) Uani 1 1 d . . . O5 O 1.1070(4) 0.0607(2) 0.74530(19) 0.0479(7) Uani 1 1 d . . . O6 O 0.4320(5) 0.1738(3) 0.6920(3) 0.0585(8) Uani 1 1 d D . . H6A H 0.374(6) 0.120(3) 0.700(4) 0.088 Uiso 1 1 d D . . H6B H 0.537(4) 0.155(4) 0.713(4) 0.088 Uiso 1 1 d D . . O7 O 0.6868(6) -0.0209(3) 0.8895(3) 0.0743(10) Uani 1 1 d D . . H7A H 0.739(8) 0.025(4) 0.854(4) 0.111 Uiso 1 1 d D . . H7B H 0.723(9) -0.014(6) 0.944(2) 0.111 Uiso 1 1 d D . . O8 O 1.2930(6) 0.0193(4) 0.9118(3) 0.0828(11) Uani 1 1 d D . . H8A H 1.238(8) 0.051(5) 0.865(3) 0.124 Uiso 1 1 d D . . H8B H 1.392(6) -0.019(6) 0.883(4) 0.124 Uiso 1 1 d D . . N1 N 0.4160(4) 0.6184(2) 0.67471(19) 0.0301(6) Uani 1 1 d . . . N2 N 0.2764(3) 0.6046(2) 0.85341(18) 0.0266(5) Uani 1 1 d . . . N3 N 0.4133(4) 0.4058(2) 0.90138(19) 0.0291(6) Uani 1 1 d . . . C2 C 0.3121(4) 0.7149(3) 0.7106(2) 0.0304(7) Uani 1 1 d . . . C3 C 0.2936(5) 0.8119(3) 0.6542(3) 0.0393(8) Uani 1 1 d . . . H3 H 0.2251 0.8779 0.6805 0.047 Uiso 1 1 calc R . . C4 C 0.3788(5) 0.8085(3) 0.5583(3) 0.0454(9) Uani 1 1 d . . . H4 H 0.3670 0.8721 0.5190 0.055 Uiso 1 1 calc R . . C5 C 0.4817(5) 0.7095(3) 0.5216(3) 0.0422(8) Uani 1 1 d . . . H5 H 0.5396 0.7056 0.4573 0.051 Uiso 1 1 calc R . . C6 C 0.4974(5) 0.6166(3) 0.5816(2) 0.0362(8) Uani 1 1 d . . . H6 H 0.5671 0.5503 0.5567 0.043 Uiso 1 1 calc R . . C8 C 0.2290(4) 0.7064(3) 0.8144(2) 0.0309(7) Uani 1 1 d . . . C9 C 0.1157(5) 0.7910(3) 0.8703(3) 0.0393(8) Uani 1 1 d . . . H9 H 0.0788 0.8611 0.8435 0.047 Uiso 1 1 calc R . . C10 C 0.0601(5) 0.7670(3) 0.9672(3) 0.0442(9) Uani 1 1 d . . . H10 H -0.0159 0.8221 1.0061 0.053 Uiso 1 1 calc R . . C11 C 0.1148(5) 0.6624(3) 1.0082(3) 0.0389(8) Uani 1 1 d . . . H11 H 0.0791 0.6475 1.0738 0.047 Uiso 1 1 calc R . . C12 C 0.2251(4) 0.5803(3) 0.9476(2) 0.0296(7) Uani 1 1 d . . . C14 C 0.3013(4) 0.4648(3) 0.9754(2) 0.0282(7) Uani 1 1 d . . . C15 C 0.2666(5) 0.4186(3) 1.0674(2) 0.0362(7) Uani 1 1 d . . . H15 H 0.1923 0.4605 1.1175 0.043 Uiso 1 1 calc R . . C16 C 0.3448(5) 0.3083(3) 1.0835(3) 0.0395(8) Uani 1 1 d . . . H16 H 0.3215 0.2753 1.1447 0.047 Uiso 1 1 calc R . . C17 C 0.4574(5) 0.2480(3) 1.0085(3) 0.0413(8) Uani 1 1 d . . . H17 H 0.5107 0.1741 1.0183 0.050 Uiso 1 1 calc R . . C18 C 0.4892(5) 0.2997(3) 0.9186(3) 0.0357(7) Uani 1 1 d . . . H18 H 0.5661 0.2594 0.8682 0.043 Uiso 1 1 calc R . . C19 C 0.9107(4) 0.2971(3) 0.6131(2) 0.0240(6) Uani 1 1 d . . . C20 C 0.9909(4) 0.1857(3) 0.6242(2) 0.0286(7) Uani 1 1 d . . . C21 C 1.0945(5) 0.1290(3) 0.5427(2) 0.0355(7) Uani 1 1 d . . . H21 H 1.1473 0.0545 0.5491 0.043 Uiso 1 1 calc R . . C22 C 1.1193(4) 0.1820(3) 0.4529(2) 0.0351(8) Uani 1 1 d . . . C23 C 1.0475(4) 0.2940(3) 0.4440(2) 0.0302(7) Uani 1 1 d . . . C24 C 0.9410(4) 0.3509(3) 0.5232(2) 0.0283(6) Uani 1 1 d . . . H24 H 0.8895 0.4256 0.5162 0.034 Uiso 1 1 calc R . . C25 C 0.7927(4) 0.3644(2) 0.6965(2) 0.0239(6) Uani 1 1 d . . . C26 C 0.9646(5) 0.1231(3) 0.7202(2) 0.0344(7) 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 Cu 0.0250(2) 0.0253(2) 0.0268(2) -0.00502(15) 0.00049(13) -0.00024(14) Cl1 0.0627(6) 0.0604(7) 0.0447(5) -0.0283(5) 0.0146(4) -0.0024(5) Cl2 0.0450(5) 0.0611(6) 0.0274(4) 0.0052(4) 0.0028(3) -0.0148(4) O1 0.0249(11) 0.0366(14) 0.0346(12) -0.0098(10) 0.0001(9) 0.0019(9) O2 0.0304(11) 0.0499(16) 0.0300(11) -0.0128(11) -0.0009(9) -0.0082(10) O3 0.0258(12) 0.0448(16) 0.0667(17) -0.0166(14) -0.0060(12) -0.0069(11) O4 0.0487(15) 0.0423(16) 0.0471(15) 0.0116(12) 0.0111(12) -0.0001(12) O5 0.0479(15) 0.0449(17) 0.0475(15) 0.0080(13) -0.0112(12) 0.0005(12) O6 0.0582(18) 0.0455(18) 0.072(2) 0.0117(16) -0.0120(15) -0.0125(14) O7 0.090(3) 0.061(2) 0.064(2) 0.0168(18) 0.0144(19) -0.0187(19) O8 0.090(3) 0.098(3) 0.065(2) 0.011(2) -0.028(2) -0.021(2) N1 0.0284(13) 0.0309(15) 0.0309(13) -0.0027(11) -0.0025(10) -0.0063(11) N2 0.0258(12) 0.0253(14) 0.0280(13) -0.0061(11) -0.0022(10) -0.0032(10) N3 0.0290(13) 0.0282(15) 0.0288(13) -0.0032(11) -0.0011(10) -0.0038(11) C2 0.0267(15) 0.0282(17) 0.0364(17) -0.0031(14) -0.0053(12) -0.0037(13) C3 0.0419(19) 0.0286(18) 0.046(2) 0.0006(15) -0.0075(15) -0.0015(15) C4 0.053(2) 0.038(2) 0.045(2) 0.0120(17) -0.0092(17) -0.0105(17) C5 0.046(2) 0.048(2) 0.0333(18) 0.0067(16) -0.0047(15) -0.0140(17) C6 0.0340(17) 0.039(2) 0.0342(17) -0.0044(15) -0.0024(13) -0.0036(14) C8 0.0276(15) 0.0282(17) 0.0369(17) -0.0058(14) -0.0071(13) -0.0025(13) C9 0.0367(18) 0.0306(19) 0.047(2) -0.0089(16) -0.0060(15) 0.0053(14) C10 0.0417(19) 0.038(2) 0.046(2) -0.0171(17) 0.0003(16) 0.0073(16) C11 0.0365(17) 0.043(2) 0.0339(17) -0.0125(16) 0.0003(14) -0.0005(15) C12 0.0266(15) 0.0313(17) 0.0298(15) -0.0056(13) -0.0012(12) -0.0035(12) C14 0.0263(15) 0.0325(18) 0.0270(15) -0.0069(13) -0.0019(12) -0.0088(13) C15 0.0392(17) 0.039(2) 0.0309(17) -0.0066(15) 0.0022(13) -0.0115(15) C16 0.0443(19) 0.043(2) 0.0334(17) 0.0027(16) -0.0022(14) -0.0173(16) C17 0.047(2) 0.032(2) 0.0430(19) 0.0007(16) -0.0051(16) -0.0066(16) C18 0.0396(18) 0.0281(18) 0.0378(18) -0.0045(14) -0.0033(14) -0.0033(14) C19 0.0193(13) 0.0242(16) 0.0279(15) -0.0039(12) -0.0009(11) -0.0035(11) C20 0.0268(15) 0.0265(17) 0.0313(16) -0.0034(13) -0.0025(12) -0.0029(12) C21 0.0360(17) 0.0276(18) 0.0384(17) -0.0049(14) 0.0007(14) 0.0014(14) C22 0.0297(16) 0.039(2) 0.0355(17) -0.0147(15) 0.0025(13) -0.0044(14) C23 0.0278(15) 0.0403(19) 0.0223(14) -0.0022(13) 0.0010(11) -0.0090(13) C24 0.0243(14) 0.0300(17) 0.0282(15) -0.0006(13) -0.0005(11) -0.0020(12) C25 0.0237(14) 0.0197(15) 0.0257(14) 0.0018(12) 0.0036(11) -0.0037(11) C26 0.0407(18) 0.0247(17) 0.0358(17) -0.0025(14) -0.0039(14) -0.0025(14) _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 Cu O1 1.931(2) . ? Cu N2 1.951(3) . ? Cu N1 2.027(3) . ? Cu N3 2.036(3) . ? Cu O3 2.214(3) . ? Cu O2 3.187(2) . ? Cl1 C22 1.734(3) . ? Cl2 C23 1.737(3) . ? O1 C25 1.273(4) . ? O2 C25 1.228(4) . ? O4 C26 1.256(4) . ? O5 C26 1.254(4) . ? N1 C6 1.342(4) . ? N1 C2 1.357(4) . ? N2 C12 1.342(4) . ? N2 C8 1.343(4) . ? N3 C18 1.342(4) . ? N3 C14 1.362(4) . ? C2 C3 1.392(5) . ? C2 C8 1.487(5) . ? C3 C4 1.385(5) . ? C4 C5 1.383(6) . ? C5 C6 1.378(5) . ? C8 C9 1.392(5) . ? C9 C10 1.382(5) . ? C10 C11 1.392(6) . ? C11 C12 1.398(5) . ? C12 C14 1.479(5) . ? C14 C15 1.382(5) . ? C15 C16 1.389(5) . ? C16 C17 1.381(5) . ? C17 C18 1.382(5) . ? C19 C24 1.393(4) . ? C19 C20 1.396(4) . ? C19 C25 1.518(4) . ? C20 C21 1.403(4) . ? C20 C26 1.514(5) . ? C21 C22 1.383(5) . ? C22 C23 1.385(5) . ? C23 C24 1.387(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu N2 168.57(10) . . ? O1 Cu N1 94.73(11) . . ? N2 Cu N1 79.81(11) . . ? O1 Cu N3 104.26(10) . . ? N2 Cu N3 79.71(11) . . ? N1 Cu N3 158.55(11) . . ? O1 Cu O3 82.14(10) . . ? N2 Cu O3 108.60(10) . . ? N1 Cu O3 100.00(11) . . ? N3 Cu O3 92.49(11) . . ? O1 Cu O2 43.55(8) . . ? N2 Cu O2 127.92(8) . . ? N1 Cu O2 104.64(9) . . ? N3 Cu O2 83.22(8) . . ? O3 Cu O2 121.03(8) . . ? C25 O1 Cu 126.2(2) . . ? C25 O2 Cu 64.17(16) . . ? C6 N1 C2 118.7(3) . . ? C6 N1 Cu 126.3(2) . . ? C2 N1 Cu 115.0(2) . . ? C12 N2 C8 122.5(3) . . ? C12 N2 Cu 118.7(2) . . ? C8 N2 Cu 118.7(2) . . ? C18 N3 C14 118.8(3) . . ? C18 N3 Cu 126.6(2) . . ? C14 N3 Cu 114.5(2) . . ? N1 C2 C3 121.5(3) . . ? N1 C2 C8 113.7(3) . . ? C3 C2 C8 124.7(3) . . ? C4 C3 C2 118.9(3) . . ? C5 C4 C3 119.3(4) . . ? C6 C5 C4 119.0(3) . . ? N1 C6 C5 122.5(3) . . ? N2 C8 C9 120.6(3) . . ? N2 C8 C2 112.7(3) . . ? C9 C8 C2 126.7(3) . . ? C10 C9 C8 117.5(3) . . ? C9 C10 C11 121.7(3) . . ? C10 C11 C12 118.0(3) . . ? N2 C12 C11 119.7(3) . . ? N2 C12 C14 113.1(3) . . ? C11 C12 C14 127.3(3) . . ? N3 C14 C15 121.7(3) . . ? N3 C14 C12 113.9(3) . . ? C15 C14 C12 124.5(3) . . ? C14 C15 C16 118.7(3) . . ? C17 C16 C15 119.8(3) . . ? C16 C17 C18 118.6(4) . . ? N3 C18 C17 122.4(3) . . ? C24 C19 C20 119.8(3) . . ? C24 C19 C25 117.6(3) . . ? C20 C19 C25 122.5(3) . . ? C19 C20 C21 118.8(3) . . ? C19 C20 C26 122.2(3) . . ? C21 C20 C26 118.9(3) . . ? C22 C21 C20 121.0(3) . . ? C21 C22 C23 119.6(3) . . ? C21 C22 Cl1 119.2(3) . . ? C23 C22 Cl1 121.2(3) . . ? C22 C23 C24 120.2(3) . . ? C22 C23 Cl2 121.5(2) . . ? C24 C23 Cl2 118.3(3) . . ? C23 C24 C19 120.4(3) . . ? O2 C25 O1 126.0(3) . . ? O2 C25 C19 120.2(3) . . ? O1 C25 C19 113.8(3) . . ? O5 C26 O4 127.0(3) . . ? O5 C26 C20 116.7(3) . . ? O4 C26 C20 116.3(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3A O2 0.830(19) 1.94(2) 2.770(3) 176(5) 1_455 O3 H3B O6 0.848(19) 1.97(2) 2.811(4) 171(5) . O6 H6A O5 0.846(19) 2.23(3) 2.987(4) 149(5) 1_455 O6 H6B O4 0.853(19) 2.15(2) 2.991(4) 170(5) . O7 H7A O4 0.85(2) 1.89(2) 2.728(4) 167(6) . O7 H7B O8 0.85(2) 1.98(3) 2.783(5) 156(6) 2_757 O8 H8A O5 0.85(2) 2.03(4) 2.825(4) 156(7) . O8 H8B O7 0.85(2) 2.18(6) 2.815(6) 131(7) 1_655 _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.927 _refine_diff_density_max 0.284 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.059 data_Compound-4 _database_code_depnum_ccdc_archive 'CCDC 649823' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H21 Cl4 Cu N3 O10' _chemical_formula_weight 800.85 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3808(6) _cell_length_b 32.937(3) _cell_length_c 13.1837(11) _cell_angle_alpha 90.00 _cell_angle_beta 99.534(2) _cell_angle_gamma 90.00 _cell_volume 3160.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4983 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 30.94 _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 1.683 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1620 _exptl_absorpt_coefficient_mu 1.094 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.7805 _exptl_absorpt_correction_T_max 0.9481 _exptl_absorpt_process_details '(Sheldrick, 1997)' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25681 _diffrn_reflns_av_R_equivalents 0.1027 _diffrn_reflns_av_sigmaI/netI 0.1389 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5553 _reflns_number_gt 2844 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0200P)^2^] 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 5553 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1091 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.0914 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 0.817 _refine_ls_restrained_S_all 0.817 _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 0.65359(8) 0.176705(17) 0.33772(4) 0.03262(19) Uani 1 1 d . . . Cl1 Cl 1.4135(2) 0.06054(4) 0.57206(11) 0.0605(5) Uani 1 1 d . . . Cl2 Cl 1.2344(2) 0.03351(4) 0.34659(11) 0.0535(4) Uani 1 1 d . . . Cl3 Cl 0.1624(2) -0.08768(4) 0.95977(12) 0.0612(5) Uani 1 1 d . . . Cl4 Cl 0.3664(2) -0.05255(4) 1.17291(11) 0.0658(5) Uani 1 1 d . . . O1 O 0.8744(4) 0.18508(9) 0.2498(2) 0.0399(9) Uani 1 1 d . . . O2 O 1.1439(5) 0.19528(10) 0.2007(3) 0.0441(10) Uani 1 1 d . . . O3 O 1.1363(6) 0.23315(11) 0.4142(3) 0.0587(13) Uani 1 1 d . . . H3A H 1.135(8) 0.2528(16) 0.441(4) 0.070 Uiso 1 1 d . . . O4 O 1.3218(6) 0.21772(11) 0.5588(3) 0.0741(14) Uani 1 1 d . . . O5 O 0.4807(5) 0.17019(10) 0.2111(3) 0.0393(10) Uani 1 1 d . . . H5A H 0.339(6) 0.1801(13) 0.213(3) 0.047 Uiso 1 1 d . . . H5B H 0.469(7) 0.1501(14) 0.178(4) 0.047 Uiso 1 1 d . . . O6 O 0.2691(6) 0.11924(12) 0.9655(3) 0.0661(14) Uani 1 1 d . . . H6 H 0.217(8) 0.1116(17) 0.905(4) 0.079 Uiso 1 1 d . . . O7 O 0.3962(6) 0.09851(11) 1.1160(3) 0.0705(13) Uani 1 1 d . . . O8 O 0.1361(6) 0.09304(12) 0.8007(3) 0.0745(14) Uani 1 1 d . . . O9 O 0.0719(6) 0.03451(11) 0.7261(3) 0.0676(13) Uani 1 1 d . . . O10 O 0.1085(8) 0.30408(13) 0.4895(4) 0.0637(15) Uani 1 1 d . . . H10A H 0.113(9) 0.3019(18) 0.548(4) 0.076 Uiso 1 1 d . . . H10B H 0.149(9) 0.3214(18) 0.475(5) 0.076 Uiso 1 1 d . . . N1 N 0.7131(5) 0.11816(12) 0.3796(3) 0.0350(11) Uani 1 1 d . . . N2 N 0.7572(5) 0.18419(13) 0.4817(3) 0.0350(10) Uani 1 1 d . . . N3 N 0.6000(5) 0.23665(11) 0.3556(3) 0.0368(11) Uani 1 1 d . . . C1 C 0.6799(7) 0.08478(16) 0.3212(4) 0.0451(15) Uani 1 1 d . . . H1 H 0.6178 0.0877 0.2542 0.054 Uiso 1 1 calc R . . C2 C 0.7334(8) 0.04622(16) 0.3556(5) 0.0533(17) Uani 1 1 d . . . H2 H 0.7096 0.0236 0.3132 0.064 Uiso 1 1 calc R . . C3 C 0.8227(8) 0.04292(18) 0.4546(5) 0.0616(19) Uani 1 1 d . . . H3 H 0.8600 0.0174 0.4803 0.074 Uiso 1 1 calc R . . C4 C 0.8586(7) 0.07569(19) 0.5163(4) 0.0545(17) Uani 1 1 d . . . H4 H 0.9214 0.0730 0.5832 0.065 Uiso 1 1 calc R . . C5 C 0.7997(7) 0.11345(17) 0.4779(4) 0.0376(14) Uani 1 1 d . . . C6 C 0.8245(7) 0.15165(17) 0.5353(4) 0.0435(15) Uani 1 1 d . . . C7 C 0.9034(8) 0.15578(19) 0.6389(4) 0.0587(18) Uani 1 1 d . . . H7 H 0.9486 0.1335 0.6784 0.070 Uiso 1 1 calc R . . C8 C 0.9110(8) 0.1944(2) 0.6799(4) 0.070(2) Uani 1 1 d . . . H8 H 0.9663 0.1982 0.7479 0.084 Uiso 1 1 calc R . . C9 C 0.8393(8) 0.22749(19) 0.6231(4) 0.0560(17) Uani 1 1 d . . . H9 H 0.8446 0.2533 0.6520 0.067 Uiso 1 1 calc R . . C10 C 0.7600(7) 0.22129(16) 0.5229(4) 0.0377(14) Uani 1 1 d . . . C11 C 0.6698(7) 0.25133(16) 0.4490(4) 0.0428(14) Uani 1 1 d . . . C12 C 0.6540(8) 0.29222(18) 0.4731(5) 0.0577(17) Uani 1 1 d . . . H12 H 0.7031 0.3022 0.5379 0.069 Uiso 1 1 calc R . . C13 C 0.5632(9) 0.31741(18) 0.3981(6) 0.073(2) Uani 1 1 d . . . H13 H 0.5522 0.3449 0.4117 0.088 Uiso 1 1 calc R . . C14 C 0.4890(8) 0.30218(17) 0.3034(5) 0.0664(19) Uani 1 1 d . . . H14 H 0.4250 0.3189 0.2529 0.080 Uiso 1 1 calc R . . C15 C 0.5115(7) 0.26194(16) 0.2853(4) 0.0490(16) Uani 1 1 d . . . H15 H 0.4628 0.2516 0.2209 0.059 Uiso 1 1 calc R . . C16 C 1.1399(6) 0.15337(14) 0.3430(4) 0.0280(12) Uani 1 1 d . . . C17 C 1.2256(6) 0.16450(14) 0.4405(4) 0.0310(13) Uani 1 1 d . . . C18 C 1.3096(6) 0.13577(16) 0.5086(4) 0.0376(14) Uani 1 1 d . . . H18 H 1.3654 0.1439 0.5738 0.045 Uiso 1 1 calc R . . C19 C 1.3131(7) 0.09531(16) 0.4826(4) 0.0384(14) Uani 1 1 d . . . C20 C 1.2344(6) 0.08344(15) 0.3855(4) 0.0348(13) Uani 1 1 d . . . C21 C 1.1473(6) 0.11206(15) 0.3164(3) 0.0353(13) Uani 1 1 d . . . H21 H 1.0927 0.1037 0.2511 0.042 Uiso 1 1 calc R . . C22 C 1.0432(7) 0.18070(15) 0.2594(4) 0.0319(12) Uani 1 1 d . . . C23 C 1.2321(7) 0.20788(17) 0.4788(4) 0.0407(15) Uani 1 1 d . . . C24 C 0.2765(6) 0.04712(15) 0.9981(4) 0.0335(13) Uani 1 1 d . . . C25 C 0.1906(6) 0.03132(14) 0.9044(4) 0.0313(13) Uani 1 1 d . . . C26 C 0.1581(6) -0.00971(15) 0.8960(4) 0.0387(14) Uani 1 1 d . . . H26 H 0.0982 -0.0199 0.8336 0.046 Uiso 1 1 calc R . . C27 C 0.2108(7) -0.03650(15) 0.9766(4) 0.0359(13) Uani 1 1 d . . . C28 C 0.2957(7) -0.02122(15) 1.0687(4) 0.0352(13) Uani 1 1 d . . . C29 C 0.3270(6) 0.01963(16) 1.0791(4) 0.0406(14) Uani 1 1 d . . . H29 H 0.3841 0.0296 1.1425 0.049 Uiso 1 1 calc R . . C30 C 0.3192(8) 0.09139(17) 1.0298(4) 0.0427(15) Uani 1 1 d . . . C31 C 0.1281(8) 0.05385(17) 0.8029(4) 0.0452(15) 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 0.0354(4) 0.0316(4) 0.0293(4) 0.0006(3) 0.0010(3) 0.0021(3) Cl1 0.0681(11) 0.0599(10) 0.0498(10) 0.0229(8) -0.0010(8) 0.0094(9) Cl2 0.0747(11) 0.0330(8) 0.0535(9) 0.0017(7) 0.0129(8) 0.0021(8) Cl3 0.0750(11) 0.0318(9) 0.0742(11) 0.0016(8) 0.0051(9) -0.0016(8) Cl4 0.0815(12) 0.0643(11) 0.0490(10) 0.0244(9) 0.0032(9) 0.0083(9) O1 0.029(2) 0.044(2) 0.046(2) 0.0088(18) 0.0041(18) 0.0019(19) O2 0.031(2) 0.049(2) 0.053(2) 0.017(2) 0.0107(19) 0.0072(19) O3 0.083(3) 0.035(3) 0.053(3) -0.010(2) -0.004(2) 0.001(3) O4 0.096(4) 0.059(3) 0.054(3) -0.017(2) -0.027(3) -0.001(2) O5 0.033(2) 0.043(3) 0.039(2) -0.0068(18) -0.0029(19) -0.001(2) O6 0.106(4) 0.037(3) 0.052(3) -0.006(2) 0.004(3) -0.014(2) O7 0.087(3) 0.053(3) 0.061(3) -0.018(2) -0.018(3) -0.009(2) O8 0.124(4) 0.037(3) 0.053(3) 0.008(2) -0.014(3) 0.008(3) O9 0.102(4) 0.057(3) 0.034(2) 0.002(2) -0.016(2) -0.003(2) O10 0.093(4) 0.045(3) 0.052(3) -0.003(3) 0.008(3) -0.004(3) N1 0.035(3) 0.035(3) 0.035(3) 0.007(2) 0.007(2) -0.001(2) N2 0.031(3) 0.050(3) 0.023(2) -0.001(2) 0.001(2) -0.003(2) N3 0.043(3) 0.028(3) 0.039(3) -0.004(2) 0.005(2) 0.002(2) C1 0.049(4) 0.039(4) 0.046(4) 0.001(3) 0.006(3) -0.004(3) C2 0.070(5) 0.034(4) 0.058(4) 0.007(3) 0.015(4) 0.006(3) C3 0.048(4) 0.048(4) 0.094(6) 0.033(4) 0.027(4) 0.013(3) C4 0.050(4) 0.062(4) 0.050(4) 0.022(4) 0.007(3) 0.009(4) C5 0.031(3) 0.048(4) 0.035(3) 0.013(3) 0.006(3) 0.003(3) C6 0.042(4) 0.056(4) 0.031(3) 0.014(3) 0.004(3) 0.002(3) C7 0.059(4) 0.078(5) 0.036(4) 0.009(4) 0.000(3) 0.004(4) C8 0.066(5) 0.099(6) 0.037(4) -0.009(4) -0.010(3) -0.001(4) C9 0.055(4) 0.065(5) 0.046(4) -0.018(4) 0.002(3) -0.010(4) C10 0.037(4) 0.040(4) 0.036(4) -0.007(3) 0.005(3) -0.010(3) C11 0.038(4) 0.039(4) 0.053(4) -0.013(3) 0.011(3) -0.006(3) C12 0.067(5) 0.045(4) 0.063(4) -0.017(4) 0.017(4) -0.002(4) C13 0.076(5) 0.037(4) 0.111(6) -0.012(4) 0.031(5) 0.003(4) C14 0.082(5) 0.038(4) 0.079(5) 0.001(4) 0.011(4) 0.014(4) C15 0.058(4) 0.037(4) 0.052(4) -0.002(3) 0.006(3) 0.000(3) C16 0.026(3) 0.039(3) 0.020(3) -0.002(3) 0.006(2) 0.004(3) C17 0.031(3) 0.030(3) 0.032(3) 0.002(3) 0.005(3) -0.004(2) C18 0.035(3) 0.053(4) 0.024(3) 0.003(3) 0.001(3) -0.007(3) C19 0.040(4) 0.042(4) 0.032(3) 0.010(3) 0.002(3) 0.007(3) C20 0.030(3) 0.035(3) 0.040(3) 0.006(3) 0.009(3) 0.001(3) C21 0.031(3) 0.052(4) 0.023(3) -0.003(3) 0.003(3) -0.007(3) C22 0.025(3) 0.031(3) 0.040(3) -0.002(3) 0.004(3) -0.005(3) C23 0.034(4) 0.042(4) 0.046(4) -0.001(3) 0.004(3) -0.006(3) C24 0.031(3) 0.036(3) 0.034(3) -0.002(3) 0.006(3) 0.000(3) C25 0.037(3) 0.026(3) 0.030(3) -0.001(3) 0.001(3) 0.002(3) C26 0.036(3) 0.044(4) 0.033(3) -0.007(3) -0.005(3) -0.002(3) C27 0.035(3) 0.036(3) 0.037(3) -0.006(3) 0.008(3) 0.001(3) C28 0.035(3) 0.037(3) 0.033(3) 0.010(3) 0.005(3) 0.003(3) C29 0.042(4) 0.055(4) 0.024(3) -0.008(3) 0.002(3) 0.002(3) C30 0.058(4) 0.033(4) 0.036(4) 0.002(3) 0.006(3) 0.002(3) C31 0.056(4) 0.042(4) 0.036(4) 0.005(3) 0.002(3) 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 O5 1.938(3) . ? Cu1 N2 1.941(4) . ? Cu1 N1 2.033(4) . ? Cu1 N3 2.035(4) . ? Cu1 O1 2.168(3) . ? Cl1 C19 1.721(5) . ? Cl2 C20 1.723(5) . ? Cl3 C27 1.730(5) . ? Cl4 C28 1.728(5) . ? O1 C22 1.240(5) . ? O2 C22 1.253(5) . ? O3 C23 1.311(6) . ? O3 H3A 0.74(5) . ? O4 C23 1.193(6) . ? O5 H5A 1.10(4) . ? O5 H5B 0.79(4) . ? O6 C30 1.262(6) . ? O6 H6 0.86(6) . ? O7 C30 1.206(6) . ? O8 C31 1.293(6) . ? O9 C31 1.210(5) . ? O10 H10A 0.78(5) . ? O10 H10B 0.68(6) . ? N1 C1 1.341(5) . ? N1 C5 1.355(5) . ? N2 C6 1.334(6) . ? N2 C10 1.336(5) . ? N3 C15 1.333(6) . ? N3 C11 1.344(6) . ? C1 C2 1.384(6) . ? C1 H1 0.9300 . ? C2 C3 1.366(7) . ? C2 H2 0.9300 . ? C3 C4 1.351(7) . ? C3 H3 0.9300 . ? C4 C5 1.385(6) . ? C4 H4 0.9300 . ? C5 C6 1.464(7) . ? C6 C7 1.400(7) . ? C7 C8 1.380(7) . ? C7 H7 0.9300 . ? C8 C9 1.377(7) . ? C8 H8 0.9300 . ? C9 C10 1.368(6) . ? C9 H9 0.9300 . ? C10 C11 1.468(7) . ? C11 C12 1.393(6) . ? C12 C13 1.377(7) . ? C12 H12 0.9300 . ? C13 C14 1.373(7) . ? C13 H13 0.9300 . ? C14 C15 1.362(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.384(6) . ? C16 C21 1.408(6) . ? C16 C22 1.508(6) . ? C17 C18 1.379(6) . ? C17 C23 1.514(6) . ? C18 C19 1.377(6) . ? C18 H18 0.9300 . ? C19 C20 1.372(6) . ? C20 C21 1.392(6) . ? C21 H21 0.9300 . ? C24 C25 1.392(6) . ? C24 C29 1.403(6) . ? C24 C30 1.535(6) . ? C25 C26 1.374(6) . ? C25 C31 1.533(6) . ? C26 C27 1.387(6) . ? C26 H26 0.9300 . ? C27 C28 1.366(6) . ? C28 C29 1.368(6) . ? C29 H29 0.9300 . ? 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 O5 Cu1 N2 162.39(16) . . ? O5 Cu1 N1 102.16(16) . . ? N2 Cu1 N1 79.79(17) . . ? O5 Cu1 N3 95.42(16) . . ? N2 Cu1 N3 79.40(17) . . ? N1 Cu1 N3 157.81(16) . . ? O5 Cu1 O1 89.94(14) . . ? N2 Cu1 O1 107.30(13) . . ? N1 Cu1 O1 96.78(13) . . ? N3 Cu1 O1 96.68(14) . . ? C22 O1 Cu1 139.6(3) . . ? C23 O3 H3A 107(5) . . ? Cu1 O5 H5A 116(2) . . ? Cu1 O5 H5B 124(4) . . ? H5A O5 H5B 104(4) . . ? C30 O6 H6 116(4) . . ? H10A O10 H10B 114(8) . . ? C1 N1 C5 117.8(4) . . ? C1 N1 Cu1 127.6(3) . . ? C5 N1 Cu1 114.5(3) . . ? C6 N2 C10 122.7(4) . . ? C6 N2 Cu1 117.9(4) . . ? C10 N2 Cu1 119.4(4) . . ? C15 N3 C11 118.8(5) . . ? C15 N3 Cu1 127.4(4) . . ? C11 N3 Cu1 113.8(4) . . ? N1 C1 C2 123.3(5) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 116.9(5) . . ? C3 C2 H2 121.6 . . ? C1 C2 H2 121.6 . . ? C4 C3 C2 121.8(6) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 118.6(6) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? N1 C5 C4 121.5(5) . . ? N1 C5 C6 113.2(5) . . ? C4 C5 C6 125.3(5) . . ? N2 C6 C7 119.8(5) . . ? N2 C6 C5 114.4(5) . . ? C7 C6 C5 125.7(5) . . ? C8 C7 C6 117.1(6) . . ? C8 C7 H7 121.5 . . ? C6 C7 H7 121.5 . . ? C9 C8 C7 122.0(5) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C10 C9 C8 118.1(5) . . ? C10 C9 H9 120.9 . . ? C8 C9 H9 120.9 . . ? N2 C10 C9 120.3(5) . . ? N2 C10 C11 111.8(5) . . ? C9 C10 C11 127.9(5) . . ? N3 C11 C12 121.5(5) . . ? N3 C11 C10 115.4(5) . . ? C12 C11 C10 123.1(5) . . ? C13 C12 C11 117.9(6) . . ? C13 C12 H12 121.1 . . ? C11 C12 H12 121.1 . . ? C14 C13 C12 120.4(6) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 118.2(6) . . ? C15 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? N3 C15 C14 123.1(5) . . ? N3 C15 H15 118.4 . . ? C14 C15 H15 118.4 . . ? C17 C16 C21 117.1(4) . . ? C17 C16 C22 127.5(4) . . ? C21 C16 C22 115.4(4) . . ? C18 C17 C16 120.6(5) . . ? C18 C17 C23 116.4(5) . . ? C16 C17 C23 123.0(5) . . ? C19 C18 C17 121.8(5) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? C20 C19 C18 119.0(5) . . ? C20 C19 Cl1 121.2(4) . . ? C18 C19 Cl1 119.8(4) . . ? C19 C20 C21 119.7(5) . . ? C19 C20 Cl2 121.9(4) . . ? C21 C20 Cl2 118.3(4) . . ? C20 C21 C16 121.6(4) . . ? C20 C21 H21 119.2 . . ? C16 C21 H21 119.2 . . ? O1 C22 O2 125.5(5) . . ? O1 C22 C16 119.4(5) . . ? O2 C22 C16 115.0(4) . . ? O4 C23 O3 124.2(5) . . ? O4 C23 C17 122.3(5) . . ? O3 C23 C17 113.5(5) . . ? C25 C24 C29 117.3(4) . . ? C25 C24 C30 129.7(5) . . ? C29 C24 C30 112.9(5) . . ? C26 C25 C24 119.1(5) . . ? C26 C25 C31 112.5(5) . . ? C24 C25 C31 128.4(5) . . ? C25 C26 C27 122.7(5) . . ? C25 C26 H26 118.6 . . ? C27 C26 H26 118.6 . . ? C28 C27 C26 118.4(5) . . ? C28 C27 Cl3 121.8(4) . . ? C26 C27 Cl3 119.7(4) . . ? C27 C28 C29 119.8(5) . . ? C27 C28 Cl4 121.3(4) . . ? C29 C28 Cl4 118.9(4) . . ? C28 C29 C24 122.6(5) . . ? C28 C29 H29 118.7 . . ? C24 C29 H29 118.7 . . ? O7 C30 O6 122.1(5) . . ? O7 C30 C24 119.0(5) . . ? O6 C30 C24 118.9(5) . . ? O9 C31 O8 121.2(5) . . ? O9 C31 C25 119.2(5) . . ? O8 C31 C25 119.6(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3A O10 0.74(5) 1.83(5) 2.559(6) 171(7) 1_655 O5 H5A O2 1.10(4) 1.51(4) 2.602(5) 172(4) 1_455 O5 H5B O7 0.79(4) 1.93(4) 2.697(5) 167(5) 1_554 O6 H6 O8 0.86(6) 1.53(6) 2.392(5) 173(6) . O10 H10A O2 0.78(5) 1.98(5) 2.754(6) 171(6) 4_466 O10 H10B O6 0.68(6) 2.16(6) 2.830(6) 167(8) 4_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.669 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.069 data_Compound-5 _database_code_depnum_ccdc_archive 'CCDC 649824' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H33 Cl Cu2 F8 N6 O18' _chemical_formula_weight 1272.31 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' F F 0.0171 0.0103 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.6704(4) _cell_length_b 25.4797(13) _cell_length_c 12.4630(7) _cell_angle_alpha 90.00 _cell_angle_beta 96.488(1) _cell_angle_gamma 90.00 _cell_volume 2420.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 8466 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 30.92 _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 1.746 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1284 _exptl_absorpt_coefficient_mu 1.050 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.7721 _exptl_absorpt_correction_T_max 0.9419 _exptl_absorpt_process_details 'SHELXTL V 6.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX AXS CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19951 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0722 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8524 _reflns_number_gt 6760 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625' _computing_cell_refinement 'SMART V 5.625' _computing_data_reduction 'SAINT V 6.23C' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V 6.10' _computing_publication_material 'SHELXTL V 6.10' _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^)+(0.0289P)^2^] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 8524 _refine_ls_number_parameters 763 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.0725 _refine_ls_wR_factor_gt 0.0700 _refine_ls_goodness_of_fit_ref 0.850 _refine_ls_restrained_S_all 0.850 _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 0.34227(7) 0.221550(19) 0.28160(4) 0.03464(15) Uani 1 1 d . . . Cu2 Cu 0.36981(6) 0.483052(19) 0.79431(4) 0.03289(14) Uani 1 1 d . . . Cl1 Cl 0.33685(18) 0.48591(7) 0.21118(10) 0.0638(4) Uani 1 1 d . . . F1 F 1.0260(4) 0.29643(11) 0.7257(2) 0.0629(8) Uani 1 1 d . . . F2 F 0.9686(4) 0.39981(12) 0.7088(2) 0.0698(9) Uani 1 1 d . . . F3 F 0.7585(4) 0.43890(10) 0.5380(3) 0.0765(10) Uani 1 1 d . . . F4 F 0.6067(3) 0.37431(10) 0.3854(2) 0.0599(8) Uani 1 1 d . . . F5 F 0.8648(4) 0.28825(11) 1.1349(2) 0.0636(8) Uani 1 1 d . . . F6 F 0.9559(4) 0.35172(12) 1.2999(2) 0.0692(9) Uani 1 1 d . . . F7 F 0.9143(4) 0.45695(12) 1.2786(2) 0.0691(9) Uani 1 1 d . . . F8 F 0.8025(4) 0.49849(11) 1.0851(2) 0.0551(8) Uani 1 1 d . . . N1 N 0.3047(5) 0.27055(15) 0.1529(3) 0.0360(10) Uani 1 1 d . . . N2 N 0.2410(5) 0.17282(15) 0.1725(3) 0.0339(10) Uani 1 1 d . . . N3 N 0.3701(5) 0.15331(15) 0.3645(3) 0.0360(10) Uani 1 1 d . . . N4 N 0.3873(5) 0.55515(14) 0.8667(3) 0.0338(9) Uani 1 1 d . . . N5 N 0.2539(5) 0.52575(15) 0.6793(3) 0.0319(9) Uani 1 1 d . . . N6 N 0.3366(5) 0.42903(15) 0.6757(3) 0.0378(10) Uani 1 1 d . . . C1 C 0.7308(6) 0.29975(16) 0.4784(3) 0.0314(10) Uani 1 1 d . . . C2 C 0.8440(5) 0.27980(17) 0.5642(3) 0.0337(11) Uani 1 1 d . . . C3 C 0.9179(6) 0.3145(2) 0.6415(3) 0.0432(12) Uani 1 1 d . . . C4 C 0.8905(6) 0.3673(2) 0.6335(4) 0.0425(13) Uani 1 1 d . . . C5 C 0.7838(6) 0.38676(19) 0.5467(4) 0.0480(13) Uani 1 1 d . . . C6 C 0.7062(6) 0.35349(19) 0.4717(4) 0.0417(12) Uani 1 1 d . . . C7 C 0.6400(6) 0.26350(18) 0.3934(3) 0.0336(11) Uani 1 1 d . . . C8 C 0.8879(6) 0.2224(2) 0.5806(3) 0.0403(11) Uani 1 1 d . . . C9 C 0.2243(6) 0.2467(2) 0.0618(4) 0.0376(12) Uani 1 1 d . . . C10 C 0.1877(7) 0.2756(2) -0.0317(4) 0.0520(15) Uani 1 1 d . . . H10 H 0.1330 0.2596 -0.0936 0.062 Uiso 1 1 calc R . . C11 C 0.2308(7) 0.3273(2) -0.0340(4) 0.0602(15) Uani 1 1 d . . . H11 H 0.2035 0.3465 -0.0971 0.072 Uiso 1 1 calc R . . C12 C 0.3140(7) 0.3511(2) 0.0559(4) 0.0554(15) Uani 1 1 d . . . H12 H 0.3460 0.3863 0.0550 0.066 Uiso 1 1 calc R . . C13 C 0.3487(6) 0.3209(2) 0.1482(4) 0.0478(13) Uani 1 1 d . . . H13 H 0.4055 0.3366 0.2098 0.057 Uiso 1 1 calc R . . C14 C 0.1833(6) 0.19209(19) 0.0741(4) 0.0368(12) Uani 1 1 d . . . C15 C 0.0959(6) 0.1590(2) -0.0020(4) 0.0507(14) Uani 1 1 d . . . H15 H 0.0534 0.1715 -0.0700 0.061 Uiso 1 1 calc R . . C16 C 0.0731(7) 0.1073(2) 0.0244(4) 0.0518(14) Uani 1 1 d . . . H16 H 0.0147 0.0847 -0.0262 0.062 Uiso 1 1 calc R . . C17 C 0.1363(6) 0.0885(2) 0.1259(4) 0.0463(14) Uani 1 1 d . . . H17 H 0.1218 0.0534 0.1438 0.056 Uiso 1 1 calc R . . C18 C 0.2207(6) 0.12271(18) 0.1994(4) 0.0337(12) Uani 1 1 d . . . C19 C 0.2996(6) 0.11124(18) 0.3104(4) 0.0356(12) Uani 1 1 d . . . C20 C 0.3103(6) 0.0616(2) 0.3564(4) 0.0457(13) Uani 1 1 d . . . H20 H 0.2654 0.0327 0.3167 0.055 Uiso 1 1 calc R . . C21 C 0.3865(7) 0.0552(2) 0.4595(4) 0.0536(15) Uani 1 1 d . . . H21 H 0.3922 0.0222 0.4916 0.064 Uiso 1 1 calc R . . C22 C 0.4545(7) 0.0982(2) 0.5149(4) 0.0550(15) Uani 1 1 d . . . H22 H 0.5081 0.0948 0.5853 0.066 Uiso 1 1 calc R . . C23 C 0.4427(6) 0.1459(2) 0.4660(4) 0.0478(14) Uani 1 1 d . . . H23 H 0.4875 0.1750 0.5051 0.057 Uiso 1 1 calc R . . C24 C 0.7597(5) 0.41430(18) 1.0077(3) 0.0308(11) Uani 1 1 d . . . C25 C 0.7733(5) 0.36018(18) 1.0188(4) 0.0361(11) Uani 1 1 d . . . C26 C 0.8415(6) 0.3399(2) 1.1194(4) 0.0440(13) Uani 1 1 d . . . C27 C 0.8928(6) 0.3725(2) 1.2042(4) 0.0457(12) Uani 1 1 d . . . C28 C 0.8755(6) 0.4253(2) 1.1945(4) 0.0431(12) Uani 1 1 d . . . C29 C 0.8135(6) 0.44583(19) 1.0946(4) 0.0404(12) Uani 1 1 d . . . C30 C 0.6752(6) 0.44256(17) 0.9067(4) 0.0318(11) Uani 1 1 d . . . C31 C 0.7205(6) 0.32665(19) 0.9217(4) 0.0418(12) Uani 1 1 d . . . C32 C 0.3077(6) 0.59418(18) 0.8045(4) 0.0330(11) Uani 1 1 d . . . C33 C 0.2998(6) 0.64447(19) 0.8426(4) 0.0427(12) Uani 1 1 d . . . H33 H 0.2467 0.6708 0.7988 0.051 Uiso 1 1 calc R . . C34 C 0.3711(7) 0.6555(2) 0.9460(5) 0.0560(15) Uani 1 1 d . . . H34 H 0.3669 0.6895 0.9728 0.067 Uiso 1 1 calc R . . C35 C 0.4486(7) 0.6162(2) 1.0097(4) 0.0502(14) Uani 1 1 d . . . H35 H 0.4949 0.6230 1.0805 0.060 Uiso 1 1 calc R . . C36 C 0.4570(6) 0.5658(2) 0.9666(4) 0.0448(13) Uani 1 1 d . . . H36 H 0.5124 0.5393 1.0088 0.054 Uiso 1 1 calc R . . C37 C 0.2329(6) 0.57656(19) 0.6958(4) 0.0345(11) Uani 1 1 d . . . C38 C 0.1437(6) 0.60781(19) 0.6164(4) 0.0433(13) Uani 1 1 d . . . H38 H 0.1266 0.6434 0.6275 0.052 Uiso 1 1 calc R . . C39 C 0.0816(6) 0.5839(2) 0.5204(4) 0.0505(14) Uani 1 1 d . . . H39 H 0.0203 0.6038 0.4661 0.061 Uiso 1 1 calc R . . C40 C 0.1078(6) 0.5320(2) 0.5034(4) 0.0440(13) Uani 1 1 d . . . H40 H 0.0647 0.5164 0.4383 0.053 Uiso 1 1 calc R . . C41 C 0.1996(6) 0.50254(19) 0.5844(4) 0.0343(12) Uani 1 1 d . . . C42 C 0.2489(6) 0.44630(18) 0.5826(4) 0.0324(11) Uani 1 1 d . . . C43 C 0.2115(6) 0.4137(2) 0.4951(3) 0.0409(12) Uani 1 1 d . . . H43 H 0.1513 0.4263 0.4314 0.049 Uiso 1 1 calc R . . C44 C 0.2643(6) 0.3620(2) 0.5030(4) 0.0498(14) Uani 1 1 d . . . H44 H 0.2430 0.3396 0.4442 0.060 Uiso 1 1 calc R . . C45 C 0.3477(6) 0.3446(2) 0.5979(4) 0.0481(13) Uani 1 1 d . . . H45 H 0.3807 0.3095 0.6060 0.058 Uiso 1 1 calc R . . C46 C 0.3831(6) 0.37918(19) 0.6818(4) 0.0416(12) Uani 1 1 d . . . H46 H 0.4427 0.3669 0.7461 0.050 Uiso 1 1 calc R . . O1 O 0.4742(4) 0.26748(12) 0.3835(2) 0.0385(8) Uani 1 1 d . . . O2 O 0.7270(4) 0.23426(14) 0.3431(3) 0.0545(10) Uani 1 1 d . . . O3 O 0.7812(5) 0.19513(14) 0.6220(3) 0.0615(10) Uani 1 1 d . . . O4 O 1.0311(5) 0.20782(13) 0.5542(3) 0.0572(9) Uani 1 1 d . . . O5 O 0.1007(5) 0.24111(16) 0.3556(3) 0.0554(11) Uani 1 1 d . . . H5A H -0.005(7) 0.239(2) 0.332(4) 0.083 Uiso 1 1 d . . . H5B H 0.109(8) 0.229(3) 0.415(4) 0.083 Uiso 1 1 d . . . O6 O 0.5086(4) 0.44188(11) 0.9001(2) 0.0362(8) Uani 1 1 d . . . O7 O 0.7655(4) 0.46620(12) 0.8469(2) 0.0415(8) Uani 1 1 d . . . O8 O 0.7126(5) 0.34394(13) 0.8337(2) 0.0544(9) Uani 1 1 d . . . O9 O 0.6812(7) 0.27832(14) 0.9438(3) 0.0795(14) Uani 1 1 d . . . H9 H 0.641(9) 0.261(3) 0.894(5) 0.119 Uiso 1 1 d . . . O10 O 0.1355(4) 0.46425(17) 0.8879(3) 0.0531(11) Uani 1 1 d . . . H10A H 0.023(7) 0.461(2) 0.875(4) 0.080 Uiso 1 1 d . . . H10B H 0.158(7) 0.472(3) 0.945(4) 0.080 Uiso 1 1 d . . . O11 O 0.3178(9) 0.5184(2) 0.2927(4) 0.158(3) Uani 1 1 d . . . O12 O 0.2883(8) 0.4350(2) 0.2501(4) 0.135(2) Uani 1 1 d . . . O13 O 0.5057(6) 0.4817(3) 0.1855(4) 0.153(2) Uani 1 1 d . . . O14 O 0.2185(5) 0.49711(17) 0.1198(3) 0.0907(14) Uani 1 1 d . . . O15 O 0.0888(7) 0.6110(2) 0.2378(4) 0.1130(18) Uani 1 1 d D . . H15A H 0.121(10) 0.639(2) 0.292(5) 0.169 Uiso 1 1 d D . . H15B H 0.164(9) 0.5787(18) 0.242(6) 0.169 Uiso 1 1 d D . . O16 O 0.5753(7) 0.2241(2) 0.7801(4) 0.1218(19) Uani 1 1 d D . . H16A H 0.660(8) 0.220(4) 0.726(5) 0.183 Uiso 1 1 d D . . H16B H 0.540(13) 0.258(2) 0.742(7) 0.183 Uiso 1 1 d D . . O17 O 0.2627(7) 0.1811(3) 0.7366(4) 0.1078(19) Uani 1 1 d . . . H17B H 0.375(10) 0.166(3) 0.713(6) 0.162 Uiso 1 1 d . . . H17A H 0.207(12) 0.190(4) 0.684(7) 0.162 Uiso 1 1 d . . . O18 O 0.2411(10) 0.0781(3) 0.7370(6) 0.184(3) 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 0.0376(3) 0.0308(3) 0.0338(3) -0.0013(3) -0.0031(2) -0.0022(3) Cu2 0.0369(3) 0.0330(3) 0.0274(3) 0.0015(3) -0.0020(2) 0.0008(3) Cl1 0.0659(9) 0.0783(10) 0.0487(7) -0.0065(8) 0.0130(7) -0.0004(9) F1 0.0699(19) 0.072(2) 0.0411(16) -0.0060(15) -0.0181(15) -0.0030(16) F2 0.069(2) 0.072(2) 0.069(2) -0.0382(18) 0.0080(16) -0.0242(17) F3 0.089(2) 0.0308(18) 0.109(3) -0.0142(17) 0.008(2) 0.0010(16) F4 0.0578(18) 0.0414(17) 0.076(2) 0.0090(15) -0.0125(16) 0.0059(14) F5 0.085(2) 0.0473(18) 0.0568(19) 0.0206(15) 0.0024(16) 0.0163(16) F6 0.080(2) 0.082(2) 0.0404(16) 0.0222(16) -0.0147(15) 0.0105(18) F7 0.081(2) 0.079(2) 0.0414(16) -0.0120(15) -0.0199(15) -0.0006(17) F8 0.0625(19) 0.0443(19) 0.0542(18) -0.0001(14) -0.0120(15) -0.0029(15) N1 0.043(2) 0.033(2) 0.032(2) 0.0047(18) 0.0043(19) -0.0026(19) N2 0.031(2) 0.034(2) 0.037(2) -0.0052(19) 0.0036(19) -0.0009(18) N3 0.035(2) 0.039(3) 0.033(2) 0.0007(19) -0.0001(18) 0.0025(19) N4 0.039(2) 0.030(2) 0.033(2) -0.0030(18) 0.0033(18) -0.0005(18) N5 0.036(2) 0.032(2) 0.027(2) 0.0020(17) 0.0011(19) 0.0048(18) N6 0.036(2) 0.040(3) 0.035(2) 0.0015(18) -0.0043(19) 0.0056(19) C1 0.036(3) 0.029(3) 0.029(2) -0.004(2) 0.003(2) 0.001(2) C2 0.034(3) 0.033(3) 0.034(3) -0.007(2) 0.005(2) 0.000(2) C3 0.042(3) 0.057(3) 0.029(3) -0.008(2) -0.002(2) -0.007(2) C4 0.046(3) 0.040(3) 0.042(3) -0.018(3) 0.008(2) -0.019(3) C5 0.044(3) 0.035(3) 0.068(4) -0.014(3) 0.016(3) -0.004(2) C6 0.034(3) 0.045(3) 0.045(3) -0.001(2) 0.000(2) 0.007(2) C7 0.041(3) 0.029(3) 0.027(3) 0.003(2) -0.009(2) -0.002(2) C8 0.048(3) 0.046(3) 0.026(2) 0.002(3) 0.002(2) 0.001(3) C9 0.040(3) 0.043(3) 0.029(3) -0.004(2) -0.002(2) -0.003(2) C10 0.072(4) 0.049(4) 0.032(3) -0.001(2) -0.010(3) -0.002(3) C11 0.075(4) 0.062(4) 0.042(3) 0.021(3) 0.000(3) 0.003(3) C12 0.061(4) 0.051(3) 0.054(4) 0.013(3) 0.005(3) -0.001(3) C13 0.048(3) 0.046(3) 0.047(3) -0.002(3) -0.004(2) 0.003(3) C14 0.039(3) 0.035(3) 0.036(3) -0.006(2) 0.005(2) -0.001(2) C15 0.051(3) 0.056(4) 0.042(3) -0.009(3) -0.008(3) 0.000(3) C16 0.049(3) 0.047(3) 0.057(3) -0.015(3) -0.004(3) -0.002(3) C17 0.048(3) 0.041(3) 0.049(3) -0.013(3) -0.003(3) -0.005(3) C18 0.033(3) 0.028(3) 0.040(3) -0.007(2) 0.006(2) 0.004(2) C19 0.032(3) 0.033(3) 0.042(3) -0.002(2) 0.004(2) 0.002(2) C20 0.049(3) 0.035(3) 0.053(3) 0.000(3) 0.002(3) 0.003(3) C21 0.063(4) 0.039(3) 0.058(4) 0.017(3) 0.009(3) 0.000(3) C22 0.064(4) 0.055(4) 0.044(3) 0.016(3) -0.007(3) 0.004(3) C23 0.043(3) 0.053(4) 0.045(3) 0.005(3) -0.005(3) -0.007(3) C24 0.026(2) 0.035(3) 0.031(3) 0.004(2) 0.001(2) -0.005(2) C25 0.031(2) 0.043(3) 0.034(3) 0.005(2) -0.001(2) -0.002(2) C26 0.039(3) 0.046(3) 0.047(3) 0.014(3) 0.002(2) 0.006(2) C27 0.040(3) 0.060(4) 0.035(3) 0.013(3) -0.006(2) 0.006(3) C28 0.036(3) 0.059(3) 0.032(3) -0.006(2) -0.006(2) 0.002(2) C29 0.036(3) 0.045(3) 0.039(3) 0.005(2) -0.001(2) 0.007(2) C30 0.036(3) 0.029(3) 0.029(3) -0.004(2) -0.001(2) 0.007(2) C31 0.045(3) 0.034(3) 0.046(3) 0.004(2) 0.004(3) 0.000(2) C32 0.033(3) 0.031(3) 0.035(3) 0.007(2) 0.007(2) -0.006(2) C33 0.054(3) 0.032(3) 0.042(3) 0.001(2) 0.007(3) 0.000(2) C34 0.064(4) 0.040(3) 0.066(4) -0.014(3) 0.016(3) -0.006(3) C35 0.065(4) 0.050(4) 0.035(3) -0.015(3) 0.000(3) -0.005(3) C36 0.053(3) 0.047(3) 0.033(3) -0.002(2) -0.002(2) -0.007(3) C37 0.038(3) 0.030(3) 0.036(3) 0.004(2) 0.006(2) -0.001(2) C38 0.055(3) 0.028(3) 0.045(3) 0.008(2) -0.002(3) 0.003(2) C39 0.052(3) 0.056(4) 0.040(3) 0.018(3) -0.007(3) -0.002(3) C40 0.055(3) 0.041(3) 0.034(3) 0.007(2) -0.003(3) -0.002(3) C41 0.029(2) 0.051(3) 0.021(2) 0.004(2) 0.000(2) -0.005(2) C42 0.034(3) 0.035(3) 0.029(3) 0.001(2) 0.007(2) -0.003(2) C43 0.044(3) 0.052(3) 0.025(2) -0.004(2) -0.004(2) 0.004(3) C44 0.051(3) 0.051(3) 0.048(3) -0.019(3) 0.008(3) 0.000(3) C45 0.049(3) 0.040(3) 0.054(3) -0.013(3) -0.001(3) 0.002(2) C46 0.044(3) 0.039(3) 0.041(3) -0.003(2) 0.001(2) 0.006(2) O1 0.0288(18) 0.043(2) 0.0417(19) -0.0098(15) -0.0058(15) -0.0017(15) O2 0.0373(18) 0.067(3) 0.059(2) -0.033(2) 0.0064(17) 0.0027(17) O3 0.063(2) 0.053(2) 0.069(2) 0.002(2) 0.011(2) -0.0065(19) O4 0.063(2) 0.056(2) 0.054(2) 0.0101(17) 0.0114(18) 0.0134(18) O5 0.042(2) 0.076(3) 0.049(2) 0.012(2) 0.0056(19) 0.011(2) O6 0.0329(18) 0.039(2) 0.0347(18) 0.0018(15) -0.0056(15) 0.0016(15) O7 0.0466(18) 0.039(2) 0.0390(18) 0.0105(16) 0.0067(16) -0.0014(16) O8 0.080(3) 0.049(2) 0.0334(19) 0.0022(17) 0.0025(18) 0.0035(19) O9 0.144(4) 0.037(2) 0.056(3) -0.0012(19) 0.003(3) -0.021(2) O10 0.0352(19) 0.083(3) 0.041(2) -0.003(2) 0.0012(18) -0.0115(19) O11 0.184(6) 0.172(6) 0.110(5) -0.085(4) -0.025(4) 0.037(5) O12 0.182(6) 0.107(4) 0.118(4) 0.038(3) 0.029(4) -0.021(4) O13 0.076(3) 0.250(7) 0.140(4) 0.039(6) 0.048(3) 0.022(5) O14 0.096(3) 0.112(4) 0.059(3) 0.009(3) -0.011(2) -0.002(3) O15 0.134(5) 0.107(4) 0.088(3) -0.026(3) -0.026(3) 0.032(4) O16 0.135(4) 0.134(4) 0.104(4) -0.077(4) 0.045(3) -0.050(4) O17 0.080(4) 0.138(5) 0.101(4) 0.024(4) -0.014(3) 0.006(3) O18 0.202(7) 0.178(7) 0.173(6) 0.055(5) 0.035(5) -0.012(5) _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 O1 1.928(3) . ? Cu1 N2 1.937(4) . ? Cu1 N3 2.022(4) . ? Cu1 N1 2.027(4) . ? Cu1 O5 2.218(4) . ? Cu2 O6 1.912(3) . ? Cu2 N5 1.934(3) . ? Cu2 N6 2.015(4) . ? Cu2 N4 2.044(4) . ? Cu2 O10 2.301(4) . ? Cl1 O11 1.332(5) . ? Cl1 O13 1.373(4) . ? Cl1 O14 1.404(4) . ? Cl1 O12 1.447(5) . ? F1 C3 1.344(5) . ? F2 C4 1.340(5) . ? F3 C5 1.345(5) . ? F4 C6 1.355(5) . ? F5 C26 1.338(5) . ? F6 C27 1.344(5) . ? F7 C28 1.330(5) . ? F8 C29 1.349(5) . ? N1 C13 1.330(6) . ? N1 C9 1.371(5) . ? N2 C18 1.334(6) . ? N2 C14 1.349(6) . ? N3 C23 1.336(5) . ? N3 C19 1.347(5) . ? N4 C36 1.327(5) . ? N4 C32 1.362(5) . ? N5 C37 1.324(6) . ? N5 C41 1.345(5) . ? N6 C46 1.319(5) . ? N6 C42 1.348(5) . ? C1 C6 1.384(6) . ? C1 C2 1.394(5) . ? C1 C7 1.515(6) . ? C2 C3 1.381(6) . ? C2 C8 1.509(7) . ? C3 C4 1.365(7) . ? C4 C5 1.374(7) . ? C5 C6 1.349(6) . ? C7 O2 1.220(5) . ? C7 O1 1.268(5) . ? C8 O3 1.230(5) . ? C8 O4 1.239(5) . ? C9 C10 1.380(6) . ? C9 C14 1.439(6) . ? C10 C11 1.358(7) . ? C10 H10 0.9300 . ? C11 C12 1.368(7) . ? C11 H11 0.9300 . ? C12 C13 1.385(6) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.385(6) . ? C15 C16 1.373(7) . ? C15 H15 0.9300 . ? C16 C17 1.389(7) . ? C16 H16 0.9300 . ? C17 C18 1.373(6) . ? C17 H17 0.9300 . ? C18 C19 1.475(6) . ? C19 C20 1.387(6) . ? C20 C21 1.360(6) . ? C20 H20 0.9300 . ? C21 C22 1.368(7) . ? C21 H21 0.9300 . ? C22 C23 1.359(7) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C29 1.373(6) . ? C24 C25 1.389(6) . ? C24 C30 1.530(6) . ? C25 C26 1.402(6) . ? C25 C31 1.499(6) . ? C26 C27 1.367(6) . ? C27 C28 1.355(6) . ? C28 C29 1.385(6) . ? C30 O7 1.230(5) . ? C30 O6 1.271(5) . ? C31 O8 1.178(5) . ? C31 O9 1.305(6) . ? C32 C33 1.370(6) . ? C32 C37 1.480(6) . ? C33 C34 1.371(7) . ? C33 H33 0.9300 . ? C34 C35 1.372(7) . ? C34 H34 0.9300 . ? C35 C36 1.394(6) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 C38 1.388(6) . ? C38 C39 1.378(6) . ? C38 H38 0.9300 . ? C39 C40 1.358(7) . ? C39 H39 0.9300 . ? C40 C41 1.385(6) . ? C40 H40 0.9300 . ? C41 C42 1.483(6) . ? C42 C43 1.375(6) . ? C43 C44 1.376(6) . ? C43 H43 0.9300 . ? C44 C45 1.355(6) . ? C44 H44 0.9300 . ? C45 C46 1.372(6) . ? C45 H45 0.9300 . ? C46 H46 0.9300 . ? O5 H5A 0.84(5) . ? O5 H5B 0.80(5) . ? O9 H9 0.79(6) . ? O10 H10A 0.87(5) . ? O10 H10B 0.74(5) . ? O15 H15A 1.001(10) . ? O15 H15B 1.006(10) . ? O16 H16A 0.993(10) . ? O16 H16B 0.997(10) . ? O17 H17B 1.02(7) . ? O17 H17A 0.78(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N2 171.98(14) . . ? O1 Cu1 N3 99.68(14) . . ? N2 Cu1 N3 79.53(16) . . ? O1 Cu1 N1 99.47(15) . . ? N2 Cu1 N1 80.20(15) . . ? N3 Cu1 N1 158.67(15) . . ? O1 Cu1 O5 89.46(14) . . ? N2 Cu1 O5 98.53(15) . . ? N3 Cu1 O5 91.46(15) . . ? N1 Cu1 O5 98.04(15) . . ? O6 Cu2 N5 173.34(15) . . ? O6 Cu2 N6 98.36(14) . . ? N5 Cu2 N6 80.26(15) . . ? O6 Cu2 N4 100.68(14) . . ? N5 Cu2 N4 79.83(15) . . ? N6 Cu2 N4 159.09(15) . . ? O6 Cu2 O10 86.69(13) . . ? N5 Cu2 O10 99.96(15) . . ? N6 Cu2 O10 100.86(15) . . ? N4 Cu2 O10 88.84(15) . . ? O11 Cl1 O13 114.5(4) . . ? O11 Cl1 O14 112.1(3) . . ? O13 Cl1 O14 111.6(3) . . ? O11 Cl1 O12 104.3(4) . . ? O13 Cl1 O12 107.0(4) . . ? O14 Cl1 O12 106.7(3) . . ? C13 N1 C9 118.9(4) . . ? C13 N1 Cu1 128.0(3) . . ? C9 N1 Cu1 113.1(3) . . ? C18 N2 C14 122.7(4) . . ? C18 N2 Cu1 119.1(3) . . ? C14 N2 Cu1 118.0(3) . . ? C23 N3 C19 117.6(4) . . ? C23 N3 Cu1 127.8(4) . . ? C19 N3 Cu1 114.5(3) . . ? C36 N4 C32 119.4(4) . . ? C36 N4 Cu2 126.7(3) . . ? C32 N4 Cu2 113.7(3) . . ? C37 N5 C41 122.4(4) . . ? C37 N5 Cu2 119.3(3) . . ? C41 N5 Cu2 118.4(3) . . ? C46 N6 C42 118.0(4) . . ? C46 N6 Cu2 127.2(3) . . ? C42 N6 Cu2 114.7(3) . . ? C6 C1 C2 118.5(4) . . ? C6 C1 C7 120.8(4) . . ? C2 C1 C7 120.7(4) . . ? C3 C2 C1 118.2(4) . . ? C3 C2 C8 117.2(4) . . ? C1 C2 C8 124.6(4) . . ? F1 C3 C4 118.1(4) . . ? F1 C3 C2 119.6(4) . . ? C4 C3 C2 122.2(4) . . ? F2 C4 C3 120.4(5) . . ? F2 C4 C5 120.6(5) . . ? C3 C4 C5 119.1(4) . . ? F3 C5 C6 121.1(5) . . ? F3 C5 C4 119.1(4) . . ? C6 C5 C4 119.8(5) . . ? C5 C6 F4 118.0(5) . . ? C5 C6 C1 122.2(5) . . ? F4 C6 C1 119.8(4) . . ? O2 C7 O1 126.9(4) . . ? O2 C7 C1 119.8(4) . . ? O1 C7 C1 113.3(4) . . ? O3 C8 O4 126.4(5) . . ? O3 C8 C2 117.1(5) . . ? O4 C8 C2 116.5(4) . . ? N1 C9 C10 119.5(5) . . ? N1 C9 C14 115.1(4) . . ? C10 C9 C14 125.4(5) . . ? C11 C10 C9 120.6(5) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.4(5) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C13 117.4(5) . . ? C11 C12 H12 121.3 . . ? C13 C12 H12 121.3 . . ? N1 C13 C12 123.2(5) . . ? N1 C13 H13 118.4 . . ? C12 C13 H13 118.4 . . ? N2 C14 C15 119.0(5) . . ? N2 C14 C9 113.3(4) . . ? C15 C14 C9 127.7(5) . . ? C16 C15 C14 119.0(5) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C17 120.6(5) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C18 C17 C16 118.5(5) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? N2 C18 C17 120.1(4) . . ? N2 C18 C19 112.2(4) . . ? C17 C18 C19 127.7(5) . . ? N3 C19 C20 121.1(4) . . ? N3 C19 C18 114.3(4) . . ? C20 C19 C18 124.5(4) . . ? C21 C20 C19 119.9(5) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C22 118.6(5) . . ? C20 C21 H21 120.7 . . ? C22 C21 H21 120.7 . . ? C23 C22 C21 119.3(5) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? N3 C23 C22 123.3(5) . . ? N3 C23 H23 118.3 . . ? C22 C23 H23 118.3 . . ? C29 C24 C25 119.3(4) . . ? C29 C24 C30 115.8(4) . . ? C25 C24 C30 124.7(4) . . ? C24 C25 C26 118.1(4) . . ? C24 C25 C31 118.4(4) . . ? C26 C25 C31 123.5(4) . . ? F5 C26 C27 117.7(4) . . ? F5 C26 C25 121.5(4) . . ? C27 C26 C25 120.8(5) . . ? F6 C27 C28 119.5(4) . . ? F6 C27 C26 119.3(5) . . ? C28 C27 C26 121.2(4) . . ? F7 C28 C27 121.4(4) . . ? F7 C28 C29 120.2(5) . . ? C27 C28 C29 118.4(4) . . ? F8 C29 C24 120.2(4) . . ? F8 C29 C28 117.8(4) . . ? C24 C29 C28 122.0(5) . . ? O7 C30 O6 126.7(4) . . ? O7 C30 C24 120.9(4) . . ? O6 C30 C24 112.1(4) . . ? O8 C31 O9 124.2(5) . . ? O8 C31 C25 121.3(5) . . ? O9 C31 C25 114.5(4) . . ? N4 C32 C33 121.3(4) . . ? N4 C32 C37 113.7(4) . . ? C33 C32 C37 125.0(4) . . ? C32 C33 C34 119.3(5) . . ? C32 C33 H33 120.3 . . ? C34 C33 H33 120.3 . . ? C33 C34 C35 119.6(5) . . ? C33 C34 H34 120.2 . . ? C35 C34 H34 120.2 . . ? C34 C35 C36 119.0(5) . . ? C34 C35 H35 120.5 . . ? C36 C35 H35 120.5 . . ? N4 C36 C35 121.2(5) . . ? N4 C36 H36 119.4 . . ? C35 C36 H36 119.4 . . ? N5 C37 C38 120.6(4) . . ? N5 C37 C32 113.4(4) . . ? C38 C37 C32 126.0(4) . . ? C39 C38 C37 117.3(5) . . ? C39 C38 H38 121.3 . . ? C37 C38 H38 121.3 . . ? C40 C39 C38 121.5(5) . . ? C40 C39 H39 119.2 . . ? C38 C39 H39 119.2 . . ? C39 C40 C41 119.1(5) . . ? C39 C40 H40 120.5 . . ? C41 C40 H40 120.5 . . ? N5 C41 C40 118.9(5) . . ? N5 C41 C42 112.6(4) . . ? C40 C41 C42 128.5(5) . . ? N6 C42 C43 121.6(4) . . ? N6 C42 C41 113.9(4) . . ? C43 C42 C41 124.5(4) . . ? C42 C43 C44 119.2(4) . . ? C42 C43 H43 120.4 . . ? C44 C43 H43 120.4 . . ? C45 C44 C43 118.8(5) . . ? C45 C44 H44 120.6 . . ? C43 C44 H44 120.6 . . ? C44 C45 C46 119.2(5) . . ? C44 C45 H45 120.4 . . ? C46 C45 H45 120.4 . . ? N6 C46 C45 123.1(5) . . ? N6 C46 H46 118.4 . . ? C45 C46 H46 118.4 . . ? C7 O1 Cu1 117.5(3) . . ? Cu1 O5 H5A 131(4) . . ? Cu1 O5 H5B 108(4) . . ? H5A O5 H5B 106(6) . . ? C30 O6 Cu2 121.0(3) . . ? C31 O9 H9 116(5) . . ? Cu2 O10 H10A 139(4) . . ? Cu2 O10 H10B 109(5) . . ? H10A O10 H10B 109(5) . . ? H15A O15 H15B 118(6) . . ? H16A O16 H16B 86(7) . . ? H17B O17 H17A 106(8) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5A O2 0.84(5) 2.08(5) 2.858(5) 155(5) 1_455 O5 H5B O4 0.80(5) 1.97(5) 2.725(5) 157(6) 1_455 O9 H9 O16 0.79(6) 1.74(6) 2.521(6) 174(8) . O10 H10A O7 0.87(5) 1.97(5) 2.827(4) 170(6) 1_455 O10 H10B O14 0.74(5) 2.27(5) 3.007(5) 178(6) 1_556 O15 H15A O3 1.001(10) 1.88(2) 2.872(6) 168(7) 2_656 O15 H15B O11 1.006(10) 1.99(2) 2.975(8) 164(7) . O15 H15B O14 1.006(10) 2.64(5) 3.451(7) 138(6) . O15 H15B Cl1 1.006(10) 2.756(19) 3.747(5) 168(6) . O16 H16A O3 0.993(10) 1.80(3) 2.762(6) 163(8) . O17 H17A O4 0.78(8) 2.04(8) 2.806(6) 171(10) 1_455 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.691 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.057 data_Compound-6 _database_code_depnum_ccdc_archive 'CCDC 649825' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H19 Cu N3 O5, 0.6(C H4 O), 2(H2 O), 0.4(H2 O)' _chemical_formula_sum 'C27.60 H26.20 Cu N3 O8' _chemical_formula_weight 591.46 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0320(10) _cell_length_b 12.785(2) _cell_length_c 14.381(2) _cell_angle_alpha 86.590(10) _cell_angle_beta 85.08(2) _cell_angle_gamma 84.950(10) _cell_volume 1281.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 5.00 _cell_measurement_theta_max 12.50 _exptl_crystal_description prism _exptl_crystal_colour 'emerald green' _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 0.910 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.72933 _exptl_absorpt_correction_T_max 0.77312 _exptl_absorpt_process_details '(Sheldrick, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Siemens P4/PC diffractometer' _diffrn_measurement_method \w:2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3 _diffrn_reflns_number 4907 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4504 _reflns_number_gt 3786 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS ver 2.1 1993' _computing_cell_refinement 'XSCANS ver 2.1 1993' _computing_data_reduction 'XSCANS ver 2.1 1993' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V 6.10' _computing_publication_material 'SHELXTL V 6.10' _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^)+(0.0510P)^2^+2.6878P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4504 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1354 _refine_ls_wR_factor_gt 0.1198 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 Cu Cu 0.32262(7) 0.52568(4) 0.73610(3) 0.03327(16) Uani 1 1 d . . . O1 O 0.2942(4) 0.3964(2) 0.6790(2) 0.0391(6) Uani 1 1 d . . . O2 O 0.0000(4) 0.4566(2) 0.6480(2) 0.0457(7) Uani 1 1 d . . . O3 O 0.6381(4) 0.4769(3) 0.7445(2) 0.0485(7) Uani 1 1 d . . . H3A H 0.7255 0.4943 0.7046 0.073 Uiso 1 1 d R . . H3B H 0.6585 0.4152 0.7671 0.073 Uiso 1 1 d R . . O4 O 0.3508(6) 0.0923(3) 0.7181(3) 0.0674(10) Uani 1 1 d . . . O5 O 0.0986(5) 0.1946(3) 0.7730(2) 0.0545(8) Uani 1 1 d . . . O6 O -0.2686(6) 0.2791(3) 0.8113(3) 0.0752(12) Uani 1 1 d . . . H6A H -0.3391 0.2390 0.7863 0.113 Uiso 1 1 d R . . H6B H -0.1532 0.2564 0.7951 0.113 Uiso 1 1 d R . . O7 O 0.5335(6) 0.0976(3) 0.8753(3) 0.0754(11) Uani 1 1 d . . . H7A H 0.4659 0.0926 0.8296 0.113 Uiso 1 1 d R . . H7B H 0.4732 0.0847 0.9268 0.113 Uiso 1 1 d R . . N1 N 0.2679(5) 0.4738(3) 0.8722(2) 0.0370(7) Uani 1 1 d . . . N2 N 0.3219(5) 0.6573(2) 0.7980(2) 0.0343(7) Uani 1 1 d . . . N3 N 0.3428(5) 0.6298(3) 0.6228(2) 0.0380(8) Uani 1 1 d . . . C2 C 0.2689(6) 0.5491(3) 0.9344(3) 0.0366(8) Uani 1 1 d . . . C3 C 0.2487(6) 0.5257(4) 1.0305(3) 0.0450(10) Uani 1 1 d . . . H3 H 0.2515 0.5797 1.0738 0.054 Uiso 1 1 d R . . C4 C 0.2259(7) 0.4217(4) 1.0621(3) 0.0546(12) Uani 1 1 d . . . H4 H 0.2097 0.4032 1.1277 0.066 Uiso 1 1 d R . . C5 C 0.2246(7) 0.3456(4) 0.9980(3) 0.0533(12) Uani 1 1 d . . . H5 H 0.2107 0.2736 1.0183 0.064 Uiso 1 1 d R . . C6 C 0.2442(7) 0.3749(3) 0.9031(3) 0.0459(10) Uani 1 1 d . . . H6 H 0.2410 0.3222 0.8585 0.055 Uiso 1 1 d R . . C8 C 0.2952(6) 0.6555(3) 0.8920(3) 0.0384(9) Uani 1 1 d . . . C9 C 0.2942(7) 0.7469(4) 0.9386(3) 0.0521(11) Uani 1 1 d . . . H9 H 0.2745 0.7466 1.0055 0.062 Uiso 1 1 d R . . C10 C 0.3235(8) 0.8385(4) 0.8853(4) 0.0595(13) Uani 1 1 d . . . H10 H 0.3249 0.9028 0.9163 0.071 Uiso 1 1 d R . . C11 C 0.3497(7) 0.8405(3) 0.7889(4) 0.0508(11) Uani 1 1 d . . . H11 H 0.3688 0.9048 0.7527 0.061 Uiso 1 1 d R . . C12 C 0.3467(6) 0.7460(3) 0.7465(3) 0.0390(9) Uani 1 1 d . . . C14 C 0.3602(6) 0.7306(3) 0.6448(3) 0.0392(9) Uani 1 1 d . . . C15 C 0.3800(6) 0.8103(3) 0.5762(3) 0.0461(10) Uani 1 1 d . . . H15 H 0.3946 0.8807 0.5925 0.055 Uiso 1 1 d R . . C16 C 0.3809(6) 0.7876(4) 0.4840(3) 0.0513(12) Uani 1 1 d . . . H16 H 0.3936 0.8425 0.4359 0.062 Uiso 1 1 d R . . C17 C 0.3602(6) 0.6864(4) 0.4601(3) 0.0496(11) Uani 1 1 d . . . H17 H 0.3590 0.6695 0.3959 0.060 Uiso 1 1 d R . . C18 C 0.3418(6) 0.6099(4) 0.5325(3) 0.0430(10) Uani 1 1 d . . . H18 H 0.3280 0.5390 0.5173 0.052 Uiso 1 1 d R . . C19 C 0.1167(5) 0.3266(3) 0.4848(3) 0.0328(8) Uani 1 1 d . . . H19 H 0.0947 0.3994 0.4650 0.039 Uiso 1 1 d R . . C20 C 0.1379(5) 0.3005(3) 0.5778(3) 0.0307(8) Uani 1 1 d . . . C21 C 0.1746(5) 0.1927(3) 0.6077(3) 0.0348(8) Uani 1 1 d . . . C22 C 0.1786(6) 0.1173(3) 0.5436(3) 0.0425(10) Uani 1 1 d . . . H22 H 0.1971 0.0447 0.5648 0.051 Uiso 1 1 d R . . C23 C 0.1639(7) 0.0638(4) 0.3806(4) 0.0533(12) Uani 1 1 d . . . H23 H 0.1812 -0.0091 0.4007 0.064 Uiso 1 1 d R . . C24 C 0.1509(8) 0.0911(4) 0.2878(4) 0.0575(13) Uani 1 1 d . . . H24 H 0.1558 0.0377 0.2433 0.069 Uiso 1 1 d R . . C25 C 0.1279(7) 0.1985(4) 0.2579(3) 0.0522(11) Uani 1 1 d . . . H25 H 0.1234 0.2178 0.1926 0.063 Uiso 1 1 d R . . C26 C 0.1148(6) 0.2751(3) 0.3209(3) 0.0407(9) Uani 1 1 d . . . H26 H 0.0944 0.3476 0.2999 0.049 Uiso 1 1 d R . . C27 C 0.1284(5) 0.2492(3) 0.4174(3) 0.0340(8) Uani 1 1 d . . . C28 C 0.1535(6) 0.1413(3) 0.4483(3) 0.0400(9) Uani 1 1 d . . . C29 C 0.1384(5) 0.3899(3) 0.6411(3) 0.0305(8) Uani 1 1 d . . . C30 C 0.2101(7) 0.1577(3) 0.7080(3) 0.0428(10) Uani 1 1 d . . . O8 O -0.0489(13) 0.0608(6) 0.9160(5) 0.052(2) Uani 0.40 1 d P A 1 H8A H -0.1308 0.0595 0.8769 0.078 Uiso 0.40 1 d PR A 1 H8B H -0.0350 0.1222 0.9292 0.078 Uiso 0.40 1 d PR A 1 C31 C 0.2561(13) 0.0746(6) 1.0364(6) 0.0532(19) Uani 0.60 1 d P B 2 H31A H 0.3636 0.1139 1.0435 0.080 Uiso 0.60 1 d PR B 2 H31B H 0.2996 0.0019 1.0293 0.080 Uiso 0.60 1 d PR B 2 H31C H 0.1674 0.0806 1.0908 0.080 Uiso 0.60 1 d PR B 2 O9 O 0.1600(16) 0.1136(7) 0.9583(7) 0.119(3) Uani 0.60 1 d P B 2 H9A H 0.1412 0.1375 0.9031 0.179 Uiso 0.60 1 d PR B 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 Cu 0.0369(3) 0.0279(2) 0.0339(3) -0.00287(17) 0.00093(18) 0.00100(18) O1 0.0423(16) 0.0325(14) 0.0428(15) -0.0092(12) -0.0065(13) 0.0027(12) O2 0.0393(16) 0.0362(15) 0.0583(19) -0.0046(13) 0.0051(14) 0.0085(12) O3 0.0360(16) 0.0517(18) 0.0557(19) -0.0002(15) 0.0022(14) 0.0013(14) O4 0.079(3) 0.060(2) 0.056(2) 0.0120(17) -0.0078(19) 0.0251(19) O5 0.060(2) 0.0532(19) 0.0448(18) 0.0095(15) 0.0083(15) 0.0052(16) O6 0.062(2) 0.057(2) 0.102(3) 0.000(2) 0.010(2) 0.0067(18) O7 0.078(3) 0.080(3) 0.070(3) 0.001(2) -0.018(2) -0.010(2) N1 0.0370(18) 0.0367(18) 0.0350(17) -0.0010(14) 0.0031(14) 0.0028(14) N2 0.0334(16) 0.0273(16) 0.0419(18) -0.0050(13) -0.0029(14) 0.0014(13) N3 0.0361(17) 0.0353(17) 0.0390(18) 0.0020(14) 0.0045(14) 0.0064(14) C2 0.0320(19) 0.040(2) 0.037(2) -0.0033(16) -0.0028(16) 0.0046(16) C3 0.043(2) 0.056(3) 0.035(2) -0.0058(19) -0.0018(18) 0.000(2) C4 0.060(3) 0.066(3) 0.036(2) 0.007(2) 0.000(2) -0.004(2) C5 0.061(3) 0.046(3) 0.051(3) 0.010(2) 0.003(2) -0.005(2) C6 0.053(3) 0.040(2) 0.042(2) -0.0002(18) 0.003(2) 0.0023(19) C8 0.037(2) 0.042(2) 0.037(2) -0.0073(17) -0.0046(16) 0.0003(17) C9 0.063(3) 0.045(3) 0.049(3) -0.015(2) -0.008(2) 0.000(2) C10 0.071(3) 0.040(2) 0.069(3) -0.019(2) -0.008(3) 0.000(2) C11 0.054(3) 0.032(2) 0.067(3) -0.008(2) -0.004(2) -0.0008(19) C12 0.034(2) 0.0282(19) 0.054(2) 0.0010(17) -0.0060(18) 0.0035(15) C14 0.0291(19) 0.035(2) 0.051(2) 0.0038(17) 0.0018(17) 0.0031(16) C15 0.038(2) 0.035(2) 0.062(3) 0.0066(19) -0.001(2) 0.0016(17) C16 0.039(2) 0.053(3) 0.057(3) 0.019(2) 0.004(2) 0.002(2) C17 0.038(2) 0.065(3) 0.040(2) 0.005(2) 0.0078(19) 0.008(2) C18 0.038(2) 0.047(2) 0.041(2) -0.0022(18) 0.0076(18) 0.0015(18) C19 0.0307(18) 0.0263(17) 0.040(2) 0.0027(15) -0.0033(16) 0.0020(14) C20 0.0242(17) 0.0269(18) 0.040(2) 0.0022(15) 0.0006(15) 0.0005(14) C21 0.0329(19) 0.0282(18) 0.041(2) 0.0045(15) 0.0025(16) -0.0002(15) C22 0.045(2) 0.0233(18) 0.058(3) 0.0015(17) -0.004(2) 0.0007(16) C23 0.059(3) 0.036(2) 0.066(3) -0.011(2) -0.006(2) 0.001(2) C24 0.061(3) 0.053(3) 0.060(3) -0.020(2) -0.003(2) 0.004(2) C25 0.052(3) 0.062(3) 0.042(2) -0.008(2) -0.002(2) -0.002(2) C26 0.036(2) 0.043(2) 0.043(2) -0.0006(18) -0.0033(17) -0.0004(17) C27 0.0285(18) 0.0309(19) 0.043(2) -0.0030(16) -0.0040(16) -0.0007(15) C28 0.037(2) 0.0301(19) 0.053(2) -0.0052(17) -0.0023(18) -0.0030(16) C29 0.036(2) 0.0238(17) 0.0298(18) 0.0034(14) 0.0044(15) -0.0031(15) C30 0.052(3) 0.0294(19) 0.044(2) 0.0116(17) -0.003(2) 0.0006(18) O8 0.070(5) 0.049(4) 0.036(4) 0.016(3) -0.010(4) -0.006(4) C31 0.065(5) 0.047(4) 0.047(4) -0.002(3) -0.011(4) 0.006(4) O9 0.150(9) 0.092(6) 0.106(7) 0.023(5) 0.016(6) -0.002(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 Cu O1 1.922(3) . ? Cu N2 1.950(3) . ? Cu N1 2.044(3) . ? Cu N3 2.046(3) . ? Cu O3 2.262(3) . ? Cu O2 2.917(3) . ? O1 C29 1.276(5) . ? O2 C29 1.237(5) . ? O4 C30 1.251(5) . ? O5 C30 1.254(5) . ? N1 C6 1.335(6) . ? N1 C2 1.353(5) . ? N2 C12 1.333(5) . ? N2 C8 1.348(5) . ? N3 C18 1.339(6) . ? N3 C14 1.363(5) . ? C2 C3 1.394(6) . ? C2 C8 1.477(6) . ? C3 C4 1.397(7) . ? C4 C5 1.380(7) . ? C5 C6 1.393(6) . ? C8 C9 1.380(6) . ? C9 C10 1.381(7) . ? C10 C11 1.381(7) . ? C11 C12 1.389(6) . ? C12 C14 1.482(6) . ? C14 C15 1.383(6) . ? C15 C16 1.372(7) . ? C16 C17 1.382(7) . ? C17 C18 1.392(6) . ? C19 C20 1.376(5) . ? C19 C27 1.418(5) . ? C20 C21 1.427(5) . ? C20 C29 1.504(5) . ? C21 C22 1.370(6) . ? C21 C30 1.520(6) . ? C22 C28 1.409(6) . ? C23 C24 1.367(7) . ? C23 C28 1.424(6) . ? C24 C25 1.413(7) . ? C25 C26 1.365(6) . ? C26 C27 1.418(6) . ? C27 C28 1.424(5) . ? C31 O9 1.405(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu N2 173.82(13) . . ? O1 Cu N1 97.83(13) . . ? N2 Cu N1 79.84(14) . . ? O1 Cu N3 102.06(13) . . ? N2 Cu N3 79.47(14) . . ? N1 Cu N3 158.20(13) . . ? O1 Cu O3 89.51(12) . . ? N2 Cu O3 96.20(13) . . ? N1 Cu O3 90.27(13) . . ? N3 Cu O3 98.68(13) . . ? O1 Cu O2 49.40(10) . . ? N2 Cu O2 125.28(11) . . ? N1 Cu O2 102.11(12) . . ? N3 Cu O2 84.46(12) . . ? O3 Cu O2 138.01(10) . . ? C29 O1 Cu 116.9(2) . . ? C29 O2 Cu 69.7(2) . . ? C6 N1 C2 119.5(4) . . ? C6 N1 Cu 126.3(3) . . ? C2 N1 Cu 114.0(3) . . ? C12 N2 C8 122.2(4) . . ? C12 N2 Cu 119.3(3) . . ? C8 N2 Cu 118.6(3) . . ? C18 N3 C14 118.2(4) . . ? C18 N3 Cu 127.8(3) . . ? C14 N3 Cu 114.0(3) . . ? N1 C2 C3 121.6(4) . . ? N1 C2 C8 114.6(3) . . ? C3 C2 C8 123.8(4) . . ? C2 C3 C4 118.4(4) . . ? C5 C4 C3 119.6(4) . . ? C4 C5 C6 118.9(4) . . ? N1 C6 C5 122.0(4) . . ? N2 C8 C9 120.4(4) . . ? N2 C8 C2 112.8(3) . . ? C9 C8 C2 126.8(4) . . ? C8 C9 C10 117.5(5) . . ? C11 C10 C9 122.2(4) . . ? C10 C11 C12 117.4(4) . . ? N2 C12 C11 120.4(4) . . ? N2 C12 C14 112.8(4) . . ? C11 C12 C14 126.7(4) . . ? N3 C14 C15 121.4(4) . . ? N3 C14 C12 114.1(4) . . ? C15 C14 C12 124.5(4) . . ? C16 C15 C14 119.4(4) . . ? C15 C16 C17 120.3(4) . . ? C16 C17 C18 117.3(4) . . ? N3 C18 C17 123.4(4) . . ? C20 C19 C27 121.9(3) . . ? C19 C20 C21 119.4(4) . . ? C19 C20 C29 116.9(3) . . ? C21 C20 C29 123.4(3) . . ? C22 C21 C20 118.9(4) . . ? C22 C21 C30 118.3(3) . . ? C20 C21 C30 122.7(4) . . ? C21 C22 C28 122.9(4) . . ? C24 C23 C28 121.4(4) . . ? C23 C24 C25 119.7(4) . . ? C26 C25 C24 120.7(4) . . ? C25 C26 C27 120.9(4) . . ? C26 C27 C19 122.5(4) . . ? C26 C27 C28 118.9(4) . . ? C19 C27 C28 118.6(4) . . ? C22 C28 C23 123.4(4) . . ? C22 C28 C27 118.1(4) . . ? C23 C28 C27 118.4(4) . . ? O2 C29 O1 123.7(4) . . ? O2 C29 C20 120.3(4) . . ? O1 C29 C20 115.7(3) . . ? O4 C30 O5 125.4(4) . . ? O4 C30 C21 115.6(4) . . ? O5 C30 C21 118.9(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3A O2 0.84 2.06 2.792(4) 145.7 1_655 O3 H3B O6 0.84 1.86 2.697(5) 173.7 1_655 O6 H6A O7 0.86 2.35 2.875(6) 119.9 1_455 O6 H6B O5 0.85 1.88 2.733(5) 172.8 . O7 H7A O4 0.85 1.86 2.701(6) 170.5 . O7 H7B O9 0.84 2.21 2.786(12) 125.8 . O8 H8A O7 0.84 2.37 3.034(10) 136.4 1_455 O8 H8B O5 0.83 2.52 2.786(8) 100.2 . O9 H9A O5 0.85 2.00 2.854(11) 179.5 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.425 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.081 ############################################################################# ### end cif file Compound 6 ############################################################################# ############################################################################# ### end cif file for Compound 1-6 #############################################################################