# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Mahammad, Ali' _publ_contact_author_email 'm ali2062@yahoo.com' _publ_author_name 'Ali Mahammad' data_in92 _database_code_depnum_ccdc_archive 'CCDC 821582' #TrackingRef '- In92.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H34 Cl2 Cu2 N8 O10' _chemical_formula_sum 'C22 H34 Cl2 Cu2 N8 O10' _chemical_formula_weight 768.57 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 'P 21/n' #_symmetry_group_name_hall '-P2yn' 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 8.9150(5) _cell_length_b 18.9641(14) _cell_length_c 9.7505(5) _cell_angle_alpha 90.00 _cell_angle_beta 112.112(6) _cell_angle_gamma 90.00 _cell_volume 1527.22(16) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Rod-shape _exptl_crystal_colour Greenish-blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 1.633 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.683 _exptl_absorpt_correction_T_max 0.783 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10545 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2695 _reflns_number_gt 2344 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+2.0000P] 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 2695 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0300 _refine_ls_R_factor_gt 0.0238 _refine_ls_wR_factor_ref 0.0633 _refine_ls_wR_factor_gt 0.0603 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _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 0.00565(3) 0.041516(13) 0.36936(3) 0.01527(9) Uani 1 1 d . . . Cl Cl 0.32299(6) -0.07728(3) 0.45348(6) 0.01882(13) Uani 1 1 d . . . O1 O -0.08976(18) -0.04089(8) 0.41645(16) 0.0185(3) Uani 1 1 d . . . O2 O 0.25332(18) -0.01158(8) 0.38079(17) 0.0205(3) Uani 1 1 d . . . O3 O 0.2011(2) -0.13076(9) 0.41413(19) 0.0288(4) Uani 1 1 d . . . O4 O 0.4502(2) -0.09750(9) 0.4044(2) 0.0301(4) Uani 1 1 d . . . O5 O 0.3887(2) -0.06742(9) 0.61080(18) 0.0370(5) Uani 1 1 d . . . C2 C -0.2094(3) -0.07615(13) 0.3067(2) 0.0250(5) Uani 1 1 d . . . H2A H -0.3116 -0.0745 0.3245 0.030 Uiso 1 1 calc R . . H2B H -0.1786 -0.1262 0.3043 0.030 Uiso 1 1 calc R . . N3 N -0.2310(2) -0.04133(9) 0.1650(2) 0.0179(4) Uani 1 1 d . . . N4 N -0.1365(2) 0.01559(9) 0.1663(2) 0.0177(4) Uani 1 1 d . . . C5 C -0.1786(3) 0.03480(12) 0.0244(2) 0.0182(5) Uani 1 1 d . . . C6 C -0.3005(3) -0.00941(12) -0.0663(2) 0.0214(5) Uani 1 1 d . . . H6 H -0.3523 -0.0070 -0.1710 0.026 Uiso 1 1 calc R . . C7 C -0.3310(3) -0.05739(12) 0.0264(2) 0.0203(5) Uani 1 1 d . . . C8 C -0.0996(3) 0.09557(12) -0.0197(3) 0.0226(5) Uani 1 1 d . . . H8A H -0.1591 0.1390 -0.0196 0.034 Uiso 1 1 calc R . . H8B H -0.1002 0.0873 -0.1191 0.034 Uiso 1 1 calc R . . H8C H 0.0124 0.1002 0.0509 0.034 Uiso 1 1 calc R . . C9 C -0.4448(3) -0.11814(13) -0.0058(3) 0.0287(6) Uani 1 1 d . . . H9A H -0.3849 -0.1621 0.0003 0.043 Uiso 1 1 calc R . . H9B H -0.5276 -0.1131 -0.1056 0.043 Uiso 1 1 calc R . . H9C H -0.4968 -0.1192 0.0666 0.043 Uiso 1 1 calc R . . N10 N 0.0922(2) 0.13309(9) 0.3421(2) 0.0177(4) Uani 1 1 d . . . N11 N 0.2487(2) 0.14242(9) 0.3579(2) 0.0182(4) Uani 1 1 d . . . H11 H 0.3229 0.1091 0.3863 0.022 Uiso 1 1 calc R . . C12 C 0.2769(3) 0.20887(11) 0.3247(2) 0.0191(5) Uani 1 1 d . . . C13 C 0.1309(3) 0.24387(12) 0.2843(2) 0.0203(5) Uani 1 1 d . . . H13 H 0.1103 0.2916 0.2537 0.024 Uiso 1 1 calc R . . C14 C 0.0194(3) 0.19520(11) 0.2971(2) 0.0188(5) Uani 1 1 d . . . C15 C 0.4405(3) 0.23334(12) 0.3369(3) 0.0247(5) Uani 1 1 d . . . H15A H 0.5045 0.2462 0.4398 0.037 Uiso 1 1 calc R . . H15B H 0.4292 0.2745 0.2731 0.037 Uiso 1 1 calc R . . H15C H 0.4954 0.1954 0.3059 0.037 Uiso 1 1 calc R . . C16 C -0.1566(3) 0.20419(13) 0.2677(3) 0.0274(5) Uani 1 1 d . . . H16A H -0.2107 0.1583 0.2447 0.041 Uiso 1 1 calc R . . H16B H -0.2053 0.2361 0.1836 0.041 Uiso 1 1 calc R . . H16C H -0.1692 0.2241 0.3556 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.02010(15) 0.01202(15) 0.01123(14) 0.00147(10) 0.00310(11) -0.00252(10) Cl 0.0228(3) 0.0132(3) 0.0163(3) 0.0003(2) 0.0027(2) 0.0006(2) O1 0.0240(8) 0.0170(8) 0.0117(7) 0.0003(6) 0.0034(6) -0.0068(6) O2 0.0246(8) 0.0155(8) 0.0213(8) 0.0047(6) 0.0085(7) 0.0039(7) O3 0.0304(9) 0.0192(8) 0.0346(10) 0.0008(7) 0.0099(8) -0.0058(7) O4 0.0256(9) 0.0229(9) 0.0430(11) 0.0034(8) 0.0143(8) 0.0061(7) O5 0.0592(13) 0.0228(9) 0.0162(9) 0.0004(7) -0.0004(8) 0.0049(9) C2 0.0334(13) 0.0233(12) 0.0139(11) 0.0001(9) 0.0040(10) -0.0111(10) N3 0.0221(10) 0.0164(9) 0.0131(9) -0.0004(7) 0.0043(8) -0.0039(8) N4 0.0217(10) 0.0143(9) 0.0155(9) 0.0007(7) 0.0053(8) -0.0030(7) C5 0.0217(11) 0.0179(11) 0.0143(11) 0.0023(9) 0.0058(9) 0.0029(9) C6 0.0252(12) 0.0225(12) 0.0127(11) 0.0000(9) 0.0027(9) -0.0008(10) C7 0.0218(11) 0.0210(12) 0.0152(11) -0.0020(9) 0.0038(9) -0.0006(9) C8 0.0295(12) 0.0203(12) 0.0171(11) 0.0028(9) 0.0079(10) -0.0012(10) C9 0.0331(14) 0.0274(13) 0.0200(12) -0.0042(10) 0.0037(11) -0.0098(11) N10 0.0197(9) 0.0146(9) 0.0155(9) 0.0013(7) 0.0029(8) -0.0018(7) N11 0.0178(9) 0.0128(9) 0.0210(10) 0.0029(7) 0.0039(8) 0.0014(7) C12 0.0248(12) 0.0140(11) 0.0170(11) 0.0001(9) 0.0061(9) -0.0038(9) C13 0.0269(12) 0.0113(10) 0.0212(12) 0.0014(9) 0.0072(10) -0.0008(9) C14 0.0226(11) 0.0154(11) 0.0158(11) -0.0012(9) 0.0044(9) -0.0004(9) C15 0.0271(12) 0.0165(11) 0.0303(13) 0.0022(10) 0.0108(10) -0.0005(10) C16 0.0248(13) 0.0206(12) 0.0358(14) 0.0006(11) 0.0104(11) 0.0002(10) _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 1.9159(15) . ? Cu O1 1.9352(15) 3_556 ? Cu N10 1.9584(18) . ? Cu N4 1.9695(18) . ? Cu O2 2.3909(15) . ? Cu Cu 3.0287(5) 3_556 ? Cl O3 1.4295(17) . ? Cl O5 1.4334(17) . ? Cl O4 1.4388(18) . ? Cl O2 1.4522(16) . ? O1 C2 1.368(3) . ? O1 Cu 1.9352(15) 3_556 ? C2 N3 1.478(3) . ? N3 C7 1.344(3) . ? N3 N4 1.366(2) . ? N4 C5 1.341(3) . ? C5 C6 1.394(3) . ? C5 C8 1.496(3) . ? C6 C7 1.379(3) . ? C7 C9 1.488(3) . ? N10 C14 1.337(3) . ? N10 N11 1.357(3) . ? N11 C12 1.348(3) . ? C12 C13 1.379(3) . ? C12 C15 1.493(3) . ? C13 C14 1.397(3) . ? C14 C16 1.495(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu O1 76.29(7) . 3_556 ? O1 Cu N10 171.44(7) . . ? O1 Cu N10 98.02(7) 3_556 . ? O1 Cu N4 82.03(7) . . ? O1 Cu N4 157.61(7) 3_556 . ? N10 Cu N4 102.85(7) . . ? O1 Cu O2 97.52(6) . . ? O1 Cu O2 88.35(6) 3_556 . ? N10 Cu O2 88.61(7) . . ? N4 Cu O2 100.10(7) . . ? O1 Cu Cu 38.37(4) . 3_556 ? O1 Cu Cu 37.92(4) 3_556 3_556 ? N10 Cu Cu 135.61(5) . 3_556 ? N4 Cu Cu 120.21(5) . 3_556 ? O2 Cu Cu 93.69(4) . 3_556 ? O3 Cl O5 110.06(11) . . ? O3 Cl O4 109.66(10) . . ? O5 Cl O4 109.55(12) . . ? O3 Cl O2 109.60(10) . . ? O5 Cl O2 109.75(10) . . ? O4 Cl O2 108.20(10) . . ? C2 O1 Cu 119.82(13) . . ? C2 O1 Cu 135.43(14) . 3_556 ? Cu O1 Cu 103.71(7) . 3_556 ? Cl O2 Cu 127.00(9) . . ? O1 C2 N3 107.56(18) . . ? C7 N3 N4 111.22(18) . . ? C7 N3 C2 129.99(19) . . ? N4 N3 C2 118.78(17) . . ? C5 N4 N3 105.84(17) . . ? C5 N4 Cu 142.54(16) . . ? N3 N4 Cu 111.60(13) . . ? N4 C5 C6 109.9(2) . . ? N4 C5 C8 121.80(19) . . ? C6 C5 C8 128.4(2) . . ? C7 C6 C5 106.3(2) . . ? N3 C7 C6 106.81(19) . . ? N3 C7 C9 121.9(2) . . ? C6 C7 C9 131.2(2) . . ? C14 N10 N11 105.89(17) . . ? C14 N10 Cu 131.19(15) . . ? N11 N10 Cu 122.76(14) . . ? C12 N11 N10 111.79(18) . . ? N11 C12 C13 106.13(19) . . ? N11 C12 C15 122.4(2) . . ? C13 C12 C15 131.4(2) . . ? C12 C13 C14 106.45(19) . . ? N10 C14 C13 109.7(2) . . ? N10 C14 C16 120.6(2) . . ? C13 C14 C16 129.7(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.321 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.059 # Attachment '- Py-Cu2.cif' data_cu2_1_0m _database_code_depnum_ccdc_archive 'CCDC 821585' #TrackingRef '- Py-Cu2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H28 Cl2 Cu2 N14 O8, CH4O' _chemical_formula_sum 'C21 H32 Cl2 Cu2 N14 O9' _chemical_formula_weight 822.61 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 10.5249(11) _cell_length_b 11.8458(13) _cell_length_c 14.1564(15) _cell_angle_alpha 92.248(4) _cell_angle_beta 96.654(3) _cell_angle_gamma 94.316(3) _cell_volume 1746.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 0.747 _cell_measurement_theta_max 0.806 _exptl_crystal_description Rod-shape _exptl_crystal_colour Yellowish-brown _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 1.437 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10511 _diffrn_reflns_av_R_equivalents 0.0903 _diffrn_reflns_av_sigmaI/netI 0.0724 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 18.51 _reflns_number_total 2610 _reflns_number_gt 1839 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0444P)^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 2610 _refine_ls_number_parameters 443 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.0976 _refine_ls_wR_factor_gt 0.0843 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 O1S O 0.9302(10) 0.7182(9) 0.4967(7) 0.148(4) Uani 1 1 d . . . H1S H 0.9108 0.6773 0.5391 0.222 Uiso 1 1 calc R . . C1S C 0.9540(16) 0.6533(14) 0.4211(12) 0.201(9) Uani 1 1 d . . . H1S1 H 0.9816 0.7011 0.3730 0.301 Uiso 1 1 calc R . . H1S2 H 0.8772 0.6080 0.3959 0.301 Uiso 1 1 calc R . . H1S3 H 1.0201 0.6047 0.4408 0.301 Uiso 1 1 calc R . . Cu1 Cu 0.51464(10) 0.62625(8) 0.53388(7) 0.0395(4) Uani 1 1 d . . . Cu2 Cu 0.95081(10) 0.87214(8) 0.99537(7) 0.0439(4) Uani 1 1 d . . . Cl3 Cl 0.7880(3) 0.5568(2) 0.6838(2) 0.0556(8) Uani 1 1 d . . . Cl4 Cl 0.9177(3) 0.8986(2) 0.7487(2) 0.0514(7) Uani 1 1 d . . . N1 N 1.0455(7) 0.6672(8) 0.9103(6) 0.046(2) Uani 1 1 d . . . N2 N 1.0470(7) 0.7328(6) 0.9910(7) 0.046(2) Uani 1 1 d . . . C1 C 1.1213(11) 0.6886(10) 1.0599(8) 0.057(3) Uani 1 1 d . . . C2 C 1.1185(10) 0.5798(9) 0.9284(9) 0.047(3) Uani 1 1 d . . . C3 C 1.1688(9) 0.5920(9) 1.0222(9) 0.052(3) Uani 1 1 d . . . H3 H 1.2240 0.5450 1.0546 0.062 Uiso 1 1 calc R . . C4 C 1.1385(9) 0.4920(8) 0.8546(7) 0.075(3) Uani 1 1 d . . . H4A H 1.0585 0.4702 0.8162 0.112 Uiso 1 1 calc R . . H4B H 1.1702 0.4269 0.8850 0.112 Uiso 1 1 calc R . . H4C H 1.1997 0.5222 0.8151 0.112 Uiso 1 1 calc R . . O1 O 0.8805(6) 0.8386(5) 0.8281(4) 0.0635(19) Uani 1 1 d . . . O2 O 1.0275(8) 0.8542(7) 0.7218(7) 0.140(4) Uani 1 1 d . . . O4 O 0.8150(8) 0.8845(6) 0.6764(5) 0.101(3) Uani 1 1 d . . . O3 O 0.9460(7) 1.0135(6) 0.7741(5) 0.101(3) Uani 1 1 d . . . O8 O 0.7207(6) 0.6321(5) 0.6227(4) 0.068(2) Uani 1 1 d . . . O7 O 0.9210(8) 0.5821(7) 0.6829(6) 0.124(3) Uani 1 1 d . . . O6 O 0.7600(9) 0.5756(7) 0.7764(5) 0.127(3) Uani 1 1 d . . . O5 O 0.7518(8) 0.4440(6) 0.6530(6) 0.110(3) Uani 1 1 d . . . N3 N 0.5718(10) 0.7659(6) 0.4716(5) 0.041(2) Uani 1 1 d . . . N4 N 0.6957(8) 0.8057(8) 0.4758(5) 0.048(2) Uani 1 1 d . . . N5 N 0.4592(9) 0.7161(6) 0.6418(5) 0.042(2) Uani 1 1 d . . . N6 N 0.5473(7) 0.7911(7) 0.6952(6) 0.043(2) Uani 1 1 d . . . C5 C 0.3452(10) 0.7296(8) 0.6698(7) 0.037(2) Uani 1 1 d . . . C9 C 0.5096(9) 0.6083(8) 0.9041(7) 0.076(3) Uani 1 1 d . . . H9A H 0.4452 0.6535 0.8752 0.114 Uiso 1 1 calc R . . H9B H 0.4700 0.5505 0.9392 0.114 Uiso 1 1 calc R . . H9C H 0.5521 0.5735 0.8554 0.114 Uiso 1 1 calc R . . C11 C 0.6017(11) 0.7217(9) 1.0607(9) 0.056(3) Uani 1 1 d . . . H11 H 0.5356 0.7079 1.0980 0.067 Uiso 1 1 calc R . . C8 C 0.2257(8) 0.6646(7) 0.6238(7) 0.067(3) Uani 1 1 d . . . H8A H 0.2385 0.6379 0.5609 0.100 Uiso 1 1 calc R . . H8B H 0.1562 0.7129 0.6197 0.100 Uiso 1 1 calc R . . H8C H 0.2054 0.6011 0.6610 0.100 Uiso 1 1 calc R . . C10 C 0.6045(11) 0.6811(8) 0.9694(9) 0.050(3) Uani 1 1 d . . . C6 C 0.3564(11) 0.8135(8) 0.7411(7) 0.045(3) Uani 1 1 d . . . H6 H 0.2908 0.8405 0.7721 0.053 Uiso 1 1 calc R . . C7 C 0.4846(12) 0.8490(8) 0.7569(7) 0.045(3) Uani 1 1 d . . . C12 C 0.7132(13) 0.7858(8) 1.0869(8) 0.055(3) Uani 1 1 d . . . N7 N 0.7867(7) 0.7894(6) 1.0139(7) 0.045(2) Uani 1 1 d . . . N8 N 0.7166(9) 0.7231(7) 0.9426(5) 0.048(2) Uani 1 1 d . . . N9 N 0.4467(7) 0.4770(6) 0.5699(6) 0.045(2) Uani 1 1 d . . . N12 N 1.1058(8) 0.9725(6) 0.9898(5) 0.046(2) Uani 1 1 d . . . N10 N 0.4258(8) 0.4457(6) 0.6477(8) 0.057(2) Uani 1 1 d . . . N13 N 1.2135(11) 0.9446(7) 0.9821(5) 0.052(2) Uani 1 1 d . . . N14 N 1.3112(10) 0.9141(8) 0.9745(8) 0.091(4) Uani 1 1 d . . . N11 N 0.4020(11) 0.4181(8) 0.7198(7) 0.102(4) Uani 1 1 d . . . C18 C 0.5800(14) 0.9306(9) 0.4079(7) 0.065(3) Uani 1 1 d . . . H18 H 0.5551 0.9953 0.3780 0.078 Uiso 1 1 calc R . . C19 C 0.4987(11) 0.8418(10) 0.4292(7) 0.047(3) Uani 1 1 d . . . C17 C 0.7029(12) 0.9087(10) 0.4377(7) 0.057(3) Uani 1 1 d . . . C20 C 0.5553(9) 0.9386(8) 0.8245(7) 0.071(3) Uani 1 1 d . . . H20A H 0.6456 0.9390 0.8200 0.106 Uiso 1 1 calc R . . H20B H 0.5393 0.9231 0.8883 0.106 Uiso 1 1 calc R . . H20C H 0.5263 1.0112 0.8086 0.106 Uiso 1 1 calc R . . C21 C 1.1450(11) 0.7412(9) 1.1590(7) 0.093(4) Uani 1 1 d . . . H21A H 1.2286 0.7814 1.1686 0.140 Uiso 1 1 calc R . . H21B H 1.1407 0.6830 1.2041 0.140 Uiso 1 1 calc R . . H21C H 1.0811 0.7931 1.1679 0.140 Uiso 1 1 calc R . . C22 C 0.3572(11) 0.8251(8) 0.4115(7) 0.080(3) Uani 1 1 d . . . H22A H 0.3327 0.7583 0.3709 0.120 Uiso 1 1 calc R . . H22B H 0.3242 0.8897 0.3811 0.120 Uiso 1 1 calc R . . H22C H 0.3227 0.8165 0.4709 0.120 Uiso 1 1 calc R . . C23 C 0.8288(10) 0.9716(9) 0.4346(7) 0.086(4) Uani 1 1 d . . . H23A H 0.8640 0.9981 0.4979 0.128 Uiso 1 1 calc R . . H23B H 0.8183 1.0351 0.3951 0.128 Uiso 1 1 calc R . . H23C H 0.8860 0.9224 0.4088 0.128 Uiso 1 1 calc R . . C24 C 0.7597(10) 0.8473(8) 1.1810(7) 0.081(3) Uani 1 1 d . . . H24A H 0.7245 0.8077 1.2311 0.121 Uiso 1 1 calc R . . H24B H 0.7325 0.9229 1.1803 0.121 Uiso 1 1 calc R . . H24C H 0.8517 0.8505 1.1915 0.121 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1S 0.114(8) 0.215(11) 0.130(9) 0.061(8) 0.026(7) 0.074(8) C1S 0.184(17) 0.24(2) 0.177(17) -0.124(15) -0.005(14) 0.094(15) Cu1 0.0464(8) 0.0331(7) 0.0402(8) 0.0030(5) 0.0094(6) 0.0033(6) Cu2 0.0453(8) 0.0337(7) 0.0532(8) 0.0044(6) 0.0070(6) 0.0047(6) Cl3 0.055(2) 0.048(2) 0.062(2) 0.0024(16) -0.0012(16) 0.0102(16) Cl4 0.053(2) 0.046(2) 0.056(2) 0.0075(16) 0.0088(18) -0.0023(16) N1 0.044(6) 0.033(5) 0.065(7) 0.000(5) 0.023(5) 0.013(5) N2 0.059(6) 0.033(5) 0.050(6) 0.004(6) 0.012(5) 0.019(4) C1 0.066(8) 0.057(9) 0.050(9) 0.025(8) 0.004(7) 0.011(7) C2 0.045(7) 0.045(8) 0.049(9) -0.006(7) 0.003(6) 0.008(6) C3 0.049(7) 0.035(8) 0.074(10) 0.015(6) 0.010(7) 0.018(6) C4 0.090(9) 0.066(8) 0.071(8) -0.003(7) 0.005(7) 0.036(7) O1 0.077(5) 0.059(4) 0.054(4) 0.022(4) 0.010(4) -0.012(4) O2 0.112(7) 0.144(8) 0.197(10) 0.052(7) 0.109(7) 0.056(7) O4 0.111(6) 0.101(6) 0.076(5) 0.033(4) -0.041(5) -0.029(5) O3 0.146(8) 0.040(5) 0.104(6) 0.002(4) -0.014(5) -0.025(5) O8 0.066(5) 0.057(4) 0.079(5) 0.020(4) -0.014(4) 0.006(4) O7 0.055(6) 0.121(7) 0.199(9) 0.054(6) 0.009(6) 0.018(5) O6 0.213(10) 0.128(7) 0.046(5) 0.009(5) 0.032(6) 0.025(7) O5 0.144(8) 0.034(5) 0.147(7) -0.005(5) -0.009(6) 0.018(5) N3 0.062(7) 0.029(5) 0.034(5) 0.007(4) 0.003(5) 0.014(6) N4 0.035(7) 0.048(7) 0.062(6) 0.002(5) 0.015(5) -0.016(5) N5 0.045(6) 0.040(5) 0.044(5) 0.001(4) 0.015(5) 0.012(5) N6 0.065(6) 0.032(5) 0.028(5) -0.013(4) 0.001(5) 0.002(5) C5 0.031(8) 0.034(7) 0.052(7) 0.012(6) 0.016(6) 0.015(6) C9 0.068(8) 0.082(8) 0.074(8) 0.021(7) -0.001(7) -0.015(7) C11 0.053(9) 0.056(7) 0.057(9) 0.008(6) 0.014(7) -0.018(7) C8 0.046(8) 0.061(7) 0.091(8) -0.005(6) 0.003(7) -0.003(6) C10 0.049(9) 0.035(7) 0.058(9) 0.008(6) -0.021(8) -0.013(6) C6 0.052(9) 0.037(7) 0.047(7) -0.004(6) 0.015(6) 0.013(6) C7 0.057(9) 0.038(7) 0.036(7) -0.005(6) -0.013(7) 0.000(7) C12 0.071(10) 0.037(7) 0.056(9) 0.001(6) 0.009(8) -0.005(7) N7 0.038(6) 0.049(6) 0.050(6) 0.006(5) 0.008(6) 0.002(5) N8 0.040(6) 0.034(5) 0.063(7) 0.006(5) -0.011(6) -0.016(4) N9 0.066(6) 0.038(5) 0.035(6) 0.008(4) 0.024(5) 0.003(4) N12 0.027(6) 0.040(5) 0.074(6) 0.001(4) 0.012(5) 0.007(5) N10 0.076(7) 0.036(6) 0.058(8) -0.005(6) 0.017(7) -0.004(5) N13 0.055(8) 0.045(6) 0.053(6) -0.006(4) 0.007(7) -0.010(6) N14 0.051(8) 0.086(8) 0.136(9) -0.023(6) 0.016(7) 0.012(7) N11 0.163(11) 0.084(8) 0.064(8) 0.012(6) 0.049(8) -0.015(7) C18 0.069(10) 0.050(9) 0.073(8) 0.025(6) -0.001(7) -0.002(8) C19 0.045(9) 0.048(8) 0.043(7) 0.001(6) -0.004(6) -0.008(8) C17 0.060(10) 0.049(9) 0.061(8) -0.002(6) 0.017(7) -0.012(8) C20 0.066(8) 0.074(8) 0.072(8) -0.012(7) -0.002(7) 0.024(7) C21 0.135(11) 0.084(9) 0.056(9) 0.000(7) -0.017(8) 0.023(8) C22 0.092(11) 0.046(7) 0.098(9) 0.023(6) -0.016(8) 0.012(7) C23 0.073(9) 0.086(9) 0.099(9) 0.018(7) 0.024(7) -0.021(8) C24 0.098(9) 0.076(8) 0.068(9) -0.003(7) 0.023(7) -0.012(7) _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 O1S C1S 1.350(12) . ? O1S H1S 0.8200 . ? C1S H1S1 0.9600 . ? C1S H1S2 0.9600 . ? C1S H1S3 0.9600 . ? Cu1 N9 1.966(7) . ? Cu1 N9 1.972(7) 2_666 ? Cu1 N3 1.991(7) . ? Cu1 N5 1.995(7) . ? Cu1 O8 2.372(6) . ? Cu2 N12 1.956(8) . ? Cu2 N7 1.971(8) . ? Cu2 N12 1.988(8) 2_777 ? Cu2 N2 2.003(7) . ? Cu2 O1 2.406(6) . ? Cl3 O6 1.390(7) . ? Cl3 O5 1.399(7) . ? Cl3 O7 1.411(8) . ? Cl3 O8 1.436(6) . ? Cl4 O2 1.391(8) . ? Cl4 O4 1.395(7) . ? Cl4 O3 1.395(6) . ? Cl4 O1 1.430(6) . ? N1 C2 1.350(10) . ? N1 N2 1.355(8) . ? N2 C1 1.327(11) . ? C1 C3 1.394(12) . ? C1 C21 1.500(12) . ? C2 C3 1.369(11) . ? C2 C4 1.488(12) . ? C3 H3 0.9300 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? N3 C19 1.341(10) . ? N3 N4 1.346(9) . ? N4 C17 1.354(11) . ? N5 C5 1.325(9) . ? N5 N6 1.371(8) . ? N6 C7 1.350(11) . ? C5 C6 1.377(11) . ? C5 C8 1.492(11) . ? C9 C10 1.480(12) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C11 C12 1.354(12) . ? C11 C10 1.366(12) . ? C11 H11 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C10 N8 1.348(11) . ? C6 C7 1.373(11) . ? C6 H6 0.9300 . ? C7 C20 1.493(11) . ? C12 N7 1.361(11) . ? C12 C24 1.504(12) . ? N7 N8 1.363(9) . ? N9 N10 1.215(10) . ? N9 Cu1 1.972(7) 2_666 ? N12 N13 1.219(10) . ? N12 Cu2 1.988(8) 2_777 ? N10 N11 1.134(10) . ? N13 N14 1.131(10) . ? C18 C17 1.361(12) . ? C18 C19 1.371(12) . ? C18 H18 0.9300 . ? C19 C22 1.479(12) . ? C17 C23 1.477(12) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? 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 C1S O1S H1S 109.5 . . ? O1S C1S H1S1 109.5 . . ? O1S C1S H1S2 109.5 . . ? H1S1 C1S H1S2 109.5 . . ? O1S C1S H1S3 109.5 . . ? H1S1 C1S H1S3 109.5 . . ? H1S2 C1S H1S3 109.5 . . ? N9 Cu1 N9 76.8(4) . 2_666 ? N9 Cu1 N3 168.8(3) . . ? N9 Cu1 N3 94.1(3) 2_666 . ? N9 Cu1 N5 96.8(3) . . ? N9 Cu1 N5 173.0(3) 2_666 . ? N3 Cu1 N5 92.0(3) . . ? N9 Cu1 O8 98.4(3) . . ? N9 Cu1 O8 95.8(3) 2_666 . ? N3 Cu1 O8 88.9(3) . . ? N5 Cu1 O8 87.5(3) . . ? N12 Cu2 N7 171.2(4) . . ? N12 Cu2 N12 75.5(4) . 2_777 ? N7 Cu2 N12 97.0(3) . 2_777 ? N12 Cu2 N2 92.6(3) . . ? N7 Cu2 N2 94.6(3) . . ? N12 Cu2 N2 167.1(3) 2_777 . ? N12 Cu2 O1 100.1(3) . . ? N7 Cu2 O1 85.1(3) . . ? N12 Cu2 O1 98.1(3) 2_777 . ? N2 Cu2 O1 88.7(3) . . ? O6 Cl3 O5 110.0(5) . . ? O6 Cl3 O7 108.1(6) . . ? O5 Cl3 O7 110.9(5) . . ? O6 Cl3 O8 109.2(5) . . ? O5 Cl3 O8 110.2(4) . . ? O7 Cl3 O8 108.5(4) . . ? O2 Cl4 O4 112.3(6) . . ? O2 Cl4 O3 108.7(5) . . ? O4 Cl4 O3 110.0(5) . . ? O2 Cl4 O1 108.0(5) . . ? O4 Cl4 O1 107.4(4) . . ? O3 Cl4 O1 110.4(4) . . ? C2 N1 N2 109.4(8) . . ? C1 N2 N1 108.2(8) . . ? C1 N2 Cu2 129.4(9) . . ? N1 N2 Cu2 122.4(8) . . ? N2 C1 C3 108.4(9) . . ? N2 C1 C21 122.2(12) . . ? C3 C1 C21 129.5(12) . . ? N1 C2 C3 107.3(8) . . ? N1 C2 C4 123.2(11) . . ? C3 C2 C4 129.5(12) . . ? C2 C3 C1 106.8(9) . . ? C2 C3 H3 126.6 . . ? C1 C3 H3 126.6 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? Cl4 O1 Cu2 129.8(3) . . ? Cl3 O8 Cu1 135.4(4) . . ? C19 N3 N4 108.4(7) . . ? C19 N3 Cu1 127.9(9) . . ? N4 N3 Cu1 123.2(8) . . ? N3 N4 C17 109.5(8) . . ? C5 N5 N6 107.9(7) . . ? C5 N5 Cu1 132.6(8) . . ? N6 N5 Cu1 119.0(7) . . ? C7 N6 N5 107.9(7) . . ? N5 C5 C6 109.8(8) . . ? N5 C5 C8 122.3(10) . . ? C6 C5 C8 127.8(11) . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C12 C11 C10 107.3(9) . . ? C12 C11 H11 126.3 . . ? C10 C11 H11 126.3 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N8 C10 C11 106.5(8) . . ? N8 C10 C9 122.0(12) . . ? C11 C10 C9 131.5(13) . . ? C7 C6 C5 105.7(8) . . ? C7 C6 H6 127.1 . . ? C5 C6 H6 127.1 . . ? N6 C7 C6 108.7(8) . . ? N6 C7 C20 120.5(11) . . ? C6 C7 C20 130.8(12) . . ? C11 C12 N7 110.5(9) . . ? C11 C12 C24 128.8(13) . . ? N7 C12 C24 120.7(11) . . ? C12 N7 N8 104.4(7) . . ? C12 N7 Cu2 133.8(9) . . ? N8 N7 Cu2 121.7(8) . . ? C10 N8 N7 111.3(8) . . ? N10 N9 Cu1 129.3(6) . . ? N10 N9 Cu1 123.5(6) . 2_666 ? Cu1 N9 Cu1 103.2(4) . 2_666 ? N13 N12 Cu2 127.1(6) . . ? N13 N12 Cu2 128.3(6) . 2_777 ? Cu2 N12 Cu2 104.5(4) . 2_777 ? N11 N10 N9 177.4(11) . . ? N14 N13 N12 177.1(10) . . ? C17 C18 C19 108.9(9) . . ? C17 C18 H18 125.6 . . ? C19 C18 H18 125.6 . . ? N3 C19 C18 107.1(9) . . ? N3 C19 C22 123.2(11) . . ? C18 C19 C22 129.7(12) . . ? N4 C17 C18 106.1(9) . . ? N4 C17 C23 120.3(12) . . ? C18 C17 C23 133.6(13) . . ? C7 C20 H20A 109.5 . . ? C7 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C7 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C1 C21 H21A 109.5 . . ? C1 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C1 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C17 C23 H23A 109.5 . . ? C17 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C17 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C12 C24 H24A 109.5 . . ? C12 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C12 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 18.51 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.313 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.066