Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 186 loop_ _publ_author_name 'Yu-Bin Dong' 'Ru-Qi Huang' 'Jian-Ping Ma' 'Mark D. Smith' 'Jin-shan Wang' 'Hans-Conrad zur Loye' _publ_contact_author_name 'Prof Yu-Bin Dong' _publ_contact_author_address ; Department of Chemistry Shandong Normal University Jinan 250014 CHINA ; _publ_contact_author_email 'YUBINDONG@SDNU.EDU.CN' _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Synthesis and Characterization of New Coordination Polymers Generated from Oxadiazole-Containing Ligand and Inorganic M(II) (M = Cu(II), Co(II)) Salts ; data_ybd3s _database_code_CSD 193468 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Cu N4 O8 S' _chemical_formula_weight 437.87 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.5067(3) _cell_length_b 10.5119(5) _cell_length_c 28.1794(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1631.19(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8102 _cell_measurement_theta_min 2.415 _cell_measurement_theta_max 28.276 _exptl_crystal_description bar _exptl_crystal_colour blue _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.783 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 892 _exptl_absorpt_coefficient_mu 1.520 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7826 _exptl_absorpt_correction_T_max 0.9350 _exptl_absorpt_process_details '(SADABS, Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD diffractometer' _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 12672 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4065 _reflns_number_gt 3704 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART NT V5.624 (Bruker, 2000)' _computing_cell_refinement 'SAINT+ NT V6.02a (Bruker, 1998)' _computing_data_reduction 'SAINT+ NT V6.02a' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V5.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL V5.1' _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^)+(0.0523P)^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 SHELXL _refine_ls_extinction_coef 0.0015(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.020(13) _refine_ls_number_reflns 4065 _refine_ls_number_parameters 262 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0859 _refine_ls_wR_factor_gt 0.0844 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _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 0.76643(6) 0.51906(3) 0.240513(11) 0.02090(10) Uani 1 1 d . . . S S 0.33983(13) 0.71037(7) 0.21255(2) 0.01952(15) Uani 1 1 d . . . C1 C 0.5191(6) 0.4056(3) 0.16075(10) 0.0251(6) Uani 1 1 d . . . H1 H 0.4218 0.3748 0.1852 0.030 Uiso 1 1 calc R . . C2 C 0.4485(5) 0.3839(3) 0.11476(10) 0.0253(6) Uani 1 1 d . . . H2 H 0.3054 0.3402 0.1083 0.030 Uiso 1 1 calc R . . C3 C 0.5934(6) 0.4278(3) 0.07792(10) 0.0244(6) Uani 1 1 d . . . C4 C 0.8075(6) 0.4890(3) 0.08931(10) 0.0297(7) Uani 1 1 d . . . H4 H 0.9120 0.5164 0.0655 0.036 Uiso 1 1 calc R . . C5 C 0.8648(6) 0.5091(3) 0.13628(11) 0.0287(7) Uani 1 1 d . . . H5 H 1.0079 0.5518 0.1436 0.034 Uiso 1 1 calc R . . C6 C 0.5081(6) 0.4040(3) 0.02965(10) 0.0261(6) Uani 1 1 d . . . C7 C 0.5066(6) 0.3942(3) -0.04482(10) 0.0250(6) Uani 1 1 d . . . C8 C 0.4903(6) 0.3719(3) -0.17556(10) 0.0282(7) Uani 1 1 d . . . H8 H 0.3855 0.3390 -0.1984 0.034 Uiso 1 1 calc R . . C9 C 0.4323(6) 0.3567(3) -0.12878(10) 0.0279(7) Uani 1 1 d . . . H9 H 0.2914 0.3138 -0.1201 0.033 Uiso 1 1 calc R . . C10 C 0.5861(6) 0.4059(3) -0.09448(10) 0.0235(6) Uani 1 1 d . . . C11 C 0.7993(6) 0.4631(3) -0.10859(10) 0.0269(6) Uani 1 1 d . . . H11 H 0.9095 0.4934 -0.0863 0.032 Uiso 1 1 calc R . . C12 C 0.8460(5) 0.4745(3) -0.15659(10) 0.0271(6) Uani 1 1 d . . . H12 H 0.9899 0.5130 -0.1662 0.033 Uiso 1 1 calc R . . N1 N 0.7217(4) 0.4693(2) 0.17209(8) 0.0226(5) Uani 1 1 d . . . N2 N 0.3021(5) 0.3569(3) 0.01835(8) 0.0351(7) Uani 1 1 d . . . N3 N 0.3006(5) 0.3500(3) -0.03115(9) 0.0359(7) Uani 1 1 d . . . N4 N 0.6916(4) 0.4321(2) -0.19007(8) 0.0233(5) Uani 1 1 d . . . O1 O 0.6514(4) 0.4317(2) -0.00846(7) 0.0264(5) Uani 1 1 d . . . O2 O 1.0723(4) 0.4203(2) 0.24185(8) 0.0259(4) Uani 1 1 d D . . H2A H 1.210(3) 0.451(4) 0.2467(14) 0.055(12) Uiso 1 1 d D . . H2B H 1.061(6) 0.357(2) 0.2596(10) 0.028(9) Uiso 1 1 d D . . O3 O 0.4428(3) 0.59870(19) 0.23986(7) 0.0227(4) Uani 1 1 d . . . O4 O 0.4266(4) 0.8270(2) 0.23520(8) 0.0273(5) Uani 1 1 d . . . O5 O 0.0726(4) 0.6996(2) 0.21687(8) 0.0287(5) Uani 1 1 d . . . O6 O 0.4134(5) 0.7027(2) 0.16333(8) 0.0375(6) Uani 1 1 d . . . O1W O 0.8141(11) 0.8263(5) 0.1208(2) 0.154(2) Uani 1 1 d . A 1 O2WA O 0.839(6) 0.812(3) 0.0164(12) 0.142(11) Uani 0.25 1 d P B 2 O2WB O 0.656(8) 0.818(3) 0.0270(11) 0.171(17) Uani 0.25 1 d P C 3 O3W O 0.7188(19) 0.7762(9) -0.0707(4) 0.116(3) Uani 0.50 1 d P D 4 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 0.02303(17) 0.02614(17) 0.01354(15) -0.00308(12) -0.00191(13) 0.00568(14) S 0.0241(3) 0.0194(3) 0.0151(3) -0.0005(3) -0.0013(3) 0.0026(3) C1 0.0286(15) 0.0294(16) 0.0173(13) -0.0022(12) 0.0037(12) 0.0013(13) C2 0.0272(15) 0.0295(16) 0.0192(14) -0.0023(12) -0.0007(12) -0.0020(13) C3 0.0288(16) 0.0282(15) 0.0160(13) -0.0016(11) 0.0001(11) 0.0032(13) C4 0.0325(15) 0.0379(17) 0.0188(13) 0.0012(12) 0.0057(12) -0.0057(14) C5 0.0271(14) 0.0356(18) 0.0234(14) -0.0059(13) -0.0008(11) -0.0017(14) C6 0.0319(16) 0.0308(16) 0.0158(13) -0.0012(12) 0.0018(12) -0.0006(13) C7 0.0317(15) 0.0292(16) 0.0142(13) -0.0015(11) -0.0036(12) -0.0002(12) C8 0.0288(16) 0.0381(18) 0.0177(14) -0.0014(12) -0.0048(12) -0.0074(14) C9 0.0272(15) 0.0391(18) 0.0173(13) 0.0015(13) 0.0000(11) -0.0094(14) C10 0.0298(15) 0.0263(15) 0.0143(12) -0.0002(11) 0.0001(11) 0.0022(12) C11 0.0292(15) 0.0333(16) 0.0182(12) 0.0006(11) -0.0075(11) -0.0028(13) C12 0.0242(13) 0.0331(16) 0.0240(14) 0.0060(13) -0.0001(11) 0.0014(13) N1 0.0260(12) 0.0270(12) 0.0148(10) -0.0027(8) 0.0000(9) 0.0061(12) N2 0.0330(15) 0.0578(18) 0.0144(11) -0.0031(11) 0.0033(11) -0.0098(14) N3 0.0324(15) 0.0596(19) 0.0158(11) -0.0029(12) 0.0005(11) -0.0122(15) N4 0.0255(12) 0.0291(12) 0.0153(10) 0.0014(9) 0.0004(10) 0.0020(10) O1 0.0320(11) 0.0347(12) 0.0125(9) -0.0011(8) -0.0016(8) -0.0048(9) O2 0.0200(10) 0.0276(11) 0.0301(11) 0.0021(10) -0.0004(10) -0.0010(8) O3 0.0235(9) 0.0234(10) 0.0213(10) 0.0033(9) 0.0022(9) 0.0061(8) O4 0.0266(10) 0.0244(11) 0.0309(12) -0.0041(9) -0.0015(9) -0.0004(8) O5 0.0243(10) 0.0295(12) 0.0324(12) -0.0038(10) -0.0069(9) 0.0018(10) O6 0.0595(16) 0.0343(13) 0.0188(10) 0.0026(9) 0.0070(10) 0.0081(12) O1W 0.141(4) 0.070(3) 0.251(7) 0.000(4) 0.085(5) -0.021(3) O2WA 0.17(3) 0.10(2) 0.15(3) 0.016(18) 0.014(19) -0.05(2) O2WB 0.28(4) 0.11(2) 0.13(2) 0.017(15) 0.10(3) 0.02(3) O3W 0.128(8) 0.105(7) 0.115(7) 0.003(5) 0.048(7) 0.032(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 Cu O3 1.9690(18) . ? Cu O2 1.979(2) . ? Cu N1 2.013(2) . ? Cu N4 2.036(2) 2_665 ? Cu O4 2.382(2) 3_645 ? S O6 1.447(2) . ? S O4 1.462(2) . ? S O5 1.481(2) . ? S O3 1.514(2) . ? C1 N1 1.340(4) . ? C1 C2 1.372(4) . ? C2 C3 1.388(4) . ? C3 C4 1.381(4) . ? C3 C6 1.461(4) . ? C4 C5 1.377(4) . ? C5 N1 1.347(4) . ? C6 N2 1.278(4) . ? C6 O1 1.364(4) . ? C7 N3 1.285(4) . ? C7 O1 1.357(4) . ? C7 C10 1.471(4) . ? C8 N4 1.340(4) . ? C8 C9 1.366(4) . ? C9 C10 1.385(4) . ? C10 C11 1.378(4) . ? C11 C12 1.382(4) . ? C12 N4 1.346(4) . ? N2 N3 1.397(3) . ? N4 Cu 2.036(2) 2_664 ? O4 Cu 2.382(2) 3_655 ? 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 O3 Cu O2 173.49(9) . . ? O3 Cu N1 89.47(9) . . ? O2 Cu N1 89.20(9) . . ? O3 Cu N4 90.26(9) . 2_665 ? O2 Cu N4 90.99(10) . 2_665 ? N1 Cu N4 179.32(11) . 2_665 ? O3 Cu O4 87.66(8) . 3_645 ? O2 Cu O4 85.97(8) . 3_645 ? N1 Cu O4 90.03(9) . 3_645 ? N4 Cu O4 89.33(9) 2_665 3_645 ? O6 S O4 111.92(14) . . ? O6 S O5 110.65(14) . . ? O4 S O5 110.67(14) . . ? O6 S O3 109.83(13) . . ? O4 S O3 107.81(12) . . ? O5 S O3 105.73(13) . . ? N1 C1 C2 123.0(3) . . ? C1 C2 C3 119.2(3) . . ? C4 C3 C2 118.2(3) . . ? C4 C3 C6 124.8(3) . . ? C2 C3 C6 117.1(3) . . ? C5 C4 C3 119.4(3) . . ? N1 C5 C4 122.6(3) . . ? N2 C6 O1 113.6(2) . . ? N2 C6 C3 125.7(3) . . ? O1 C6 C3 120.7(3) . . ? N3 C7 O1 113.4(3) . . ? N3 C7 C10 125.3(3) . . ? O1 C7 C10 121.3(3) . . ? N4 C8 C9 122.9(3) . . ? C8 C9 C10 119.1(3) . . ? C11 C10 C9 118.9(3) . . ? C11 C10 C7 124.4(3) . . ? C9 C10 C7 116.8(3) . . ? C10 C11 C12 118.6(3) . . ? N4 C12 C11 122.7(3) . . ? C1 N1 C5 117.6(2) . . ? C1 N1 Cu 117.40(19) . . ? C5 N1 Cu 124.4(2) . . ? C6 N2 N3 105.9(2) . . ? C7 N3 N2 106.0(2) . . ? C8 N4 C12 117.7(2) . . ? C8 N4 Cu 120.41(19) . 2_664 ? C12 N4 Cu 121.2(2) . 2_664 ? C7 O1 C6 101.1(2) . . ? S O3 Cu 132.33(12) . . ? S O4 Cu 133.64(12) . 3_655 ? 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 O2 H2B O5 0.837(5) 1.925(15) 2.715(3) 157(3) 3_645 O2 H2A O4 0.838(5) 2.44(3) 2.999(3) 125(3) 3_745 O2 H2A O3 0.838(5) 2.02(2) 2.772(3) 149(4) 1_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.513 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.104 data_compound_2 _database_code_CSD 193469 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; [Co (C12H8N4O) (CH3OH)2 (SO4)] CH3OH 3.5(H2O) ; _chemical_formula_sum 'C15 H27 Co N4 O11.50 S' _chemical_formula_weight 538.40 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Co' 'Co' 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 24.1596(18) _cell_length_b 12.5832(9) _cell_length_c 14.9739(11) _cell_angle_alpha 90.00 _cell_angle_beta 91.791(2) _cell_angle_gamma 90.00 _cell_volume 4549.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 190(2) _cell_measurement_reflns_used 3454 _cell_measurement_theta_min 2.678 _cell_measurement_theta_max 26.382 _exptl_crystal_description bar _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2240 _exptl_absorpt_coefficient_mu 0.911 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 190(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 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 12243 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0956 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 26.39 _reflns_number_total 4657 _reflns_number_gt 2635 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART NT V5.624 (Bruker, 2000)' _computing_cell_refinement 'SAINT+ NT V6.02a (Bruker, 1998)' _computing_data_reduction 'SAINT+ NT V6.02a' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V5.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL V5.1' _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^)+(0.0202P)^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 4657 _refine_ls_number_parameters 325 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0922 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0894 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.5000 0.0000 0.5000 0.0183(2) Uani 1 2 d S . . Co2 Co 0.5000 0.5000 0.5000 0.01741(19) Uani 1 2 d S . . C1 C 0.39041(17) 0.0032(3) 0.3857(2) 0.0253(10) Uani 1 1 d . . . H1 H 0.4069 -0.0577 0.3600 0.030 Uiso 1 1 calc R . . C2 C 0.33862(17) 0.0334(3) 0.3537(3) 0.0239(10) Uani 1 1 d . . . H2 H 0.3198 -0.0064 0.3082 0.029 Uiso 1 1 calc R . . C3 C 0.31476(16) 0.1232(3) 0.3897(2) 0.0199(9) Uani 1 1 d . . . C4 C 0.34384(16) 0.1781(3) 0.4573(2) 0.0221(10) Uani 1 1 d . . . H4 H 0.3286 0.2400 0.4833 0.027 Uiso 1 1 calc R . . C5 C 0.39488(16) 0.1408(3) 0.4852(3) 0.0243(10) Uani 1 1 d . . . H5 H 0.4142 0.1782 0.5316 0.029 Uiso 1 1 calc R . . C6 C 0.26036(16) 0.1620(3) 0.3583(2) 0.0206(9) Uani 1 1 d . . . C7 C 0.18382(16) 0.1612(3) 0.2837(2) 0.0211(9) Uani 1 1 d . . . C8 C 0.05352(16) 0.1438(3) 0.1443(2) 0.0217(9) Uani 1 1 d . . . H8 H 0.0200 0.1825 0.1354 0.026 Uiso 1 1 calc R . . C9 C 0.09204(16) 0.1798(3) 0.2082(2) 0.0231(10) Uani 1 1 d . . . H9 H 0.0850 0.2413 0.2428 0.028 Uiso 1 1 calc R . . C10 C 0.14126(16) 0.1234(3) 0.2203(2) 0.0197(9) Uani 1 1 d . . . C11 C 0.14988(17) 0.0338(3) 0.1689(2) 0.0245(10) Uani 1 1 d . . . H11 H 0.1833 -0.0056 0.1754 0.029 Uiso 1 1 calc R . . C12 C 0.10891(16) 0.0029(3) 0.1079(3) 0.0240(10) Uani 1 1 d . . . H12 H 0.1146 -0.0596 0.0737 0.029 Uiso 1 1 calc R . . C13 C 0.4792(2) -0.0659(4) 0.6995(3) 0.0419(13) Uani 1 1 d . . . H13A H 0.4839 -0.1354 0.6711 0.063 Uiso 1 1 calc R . . H13B H 0.4462 -0.0672 0.7358 0.063 Uiso 1 1 calc R . . H13C H 0.5118 -0.0500 0.7377 0.063 Uiso 1 1 calc R . . C14 C 0.39954(18) 0.4316(3) 0.6154(3) 0.0358(12) Uani 1 1 d . . . H14A H 0.4130 0.3629 0.5941 0.054 Uiso 1 1 calc R . . H14B H 0.3634 0.4470 0.5869 0.054 Uiso 1 1 calc R . . H14C H 0.3959 0.4289 0.6804 0.054 Uiso 1 1 calc R . . C22 C 0.6738(3) 0.1098(5) 0.4114(4) 0.095(2) Uani 1 1 d . . . H22B H 0.6997 0.0970 0.4621 0.143 Uiso 1 1 calc R . . H22C H 0.6932 0.1010 0.3554 0.143 Uiso 1 1 calc R . . H22D H 0.6432 0.0588 0.4133 0.143 Uiso 1 1 calc R . . N1 N 0.41912(13) 0.0543(3) 0.4509(2) 0.0214(8) Uani 1 1 d . . . N2 N 0.23682(12) 0.2512(3) 0.37556(19) 0.0252(7) Uani 1 1 d . . . N3 N 0.18622(12) 0.2506(3) 0.32654(19) 0.0262(8) Uani 1 1 d . . . N4 N 0.06160(13) 0.0566(2) 0.0947(2) 0.0196(8) Uani 1 1 d . . . O1 O 0.22955(11) 0.0999(2) 0.30080(16) 0.0222(7) Uani 1 1 d . . . O2 O 0.47284(11) 0.0155(2) 0.63100(17) 0.0243(7) Uani 1 1 d D . . H2A H 0.4843(16) 0.0798(19) 0.646(2) 0.036 Uiso 1 1 d D . . O3 O 0.43820(11) 0.5136(2) 0.59313(18) 0.0257(7) Uani 1 1 d D . . H3A H 0.4326(17) 0.570(2) 0.623(2) 0.039 Uiso 1 1 d D . . S1 S 0.53598(4) 0.24264(9) 0.56721(7) 0.0252(2) Uani 1 1 d . . . O11 O 0.59631(12) 0.2559(3) 0.5732(2) 0.0581(10) Uani 1 1 d . . . O12 O 0.51011(11) 0.3410(2) 0.53496(17) 0.0280(7) Uani 1 1 d . . . O13 O 0.52351(11) 0.1574(2) 0.50126(17) 0.0264(7) Uani 1 1 d . . . O14 O 0.51381(15) 0.2127(2) 0.65292(18) 0.0483(10) Uani 1 1 d . . . O21 O 0.41242(17) 0.6686(3) 0.6999(2) 0.0511(10) Uani 1 1 d D . . H21A H 0.3870(17) 0.713(3) 0.674(3) 0.077 Uiso 1 1 d D . . H21B H 0.4267(19) 0.693(4) 0.751(2) 0.077 Uiso 1 1 d D . . O22 O 0.6526(2) 0.2148(4) 0.4165(3) 0.1050(17) Uani 1 1 d . . . H22A H 0.6346 0.2222 0.4743 0.157 Uiso 1 1 d R . . O23 O 0.6994(4) 0.2564(7) 0.6723(6) 0.269(4) Uani 1 1 d . . . O24 O 0.7328(11) 0.4477(17) 0.4894(16) 0.272(17) Uani 0.50 1 d P . . O25 O 0.7304(7) 0.3978(13) 0.4064(19) 0.261(11) Uani 0.50 1 d P . . O26 O 0.7361(6) 0.3452(11) 0.3005(9) 0.153(5) Uani 0.50 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0187(4) 0.0152(5) 0.0206(4) -0.0008(4) -0.0043(4) -0.0001(4) Co2 0.0185(4) 0.0136(4) 0.0198(4) 0.0000(4) -0.0052(3) -0.0003(4) C1 0.027(3) 0.022(3) 0.027(2) -0.002(2) -0.005(2) 0.007(2) C2 0.029(3) 0.019(3) 0.024(2) -0.0036(19) -0.006(2) -0.0013(19) C3 0.021(2) 0.018(2) 0.021(2) 0.0041(18) -0.0020(18) -0.0036(18) C4 0.022(2) 0.019(2) 0.024(2) -0.0034(19) -0.0062(19) 0.0033(18) C5 0.024(2) 0.024(3) 0.024(2) -0.007(2) -0.0056(19) 0.001(2) C6 0.022(2) 0.021(2) 0.018(2) -0.0016(19) -0.0035(18) -0.0031(19) C7 0.019(2) 0.023(3) 0.022(2) 0.0023(19) -0.0024(18) 0.0022(19) C8 0.020(2) 0.019(2) 0.026(2) -0.0038(19) -0.0028(18) 0.0027(18) C9 0.023(2) 0.022(2) 0.024(2) -0.0062(19) -0.0054(19) 0.0041(19) C10 0.019(2) 0.020(2) 0.020(2) 0.0023(18) -0.0011(18) -0.0037(18) C11 0.020(2) 0.022(3) 0.031(2) 0.002(2) -0.005(2) 0.0036(18) C12 0.025(3) 0.018(2) 0.029(2) -0.003(2) -0.004(2) 0.003(2) C13 0.054(3) 0.040(3) 0.032(3) 0.001(2) 0.005(2) -0.001(3) C14 0.037(3) 0.034(3) 0.037(3) 0.002(2) 0.007(2) -0.012(2) C22 0.119(7) 0.056(5) 0.113(6) 0.005(4) 0.045(5) 0.030(4) N1 0.0199(19) 0.019(2) 0.0246(18) -0.0008(16) -0.0048(16) 0.0020(15) N2 0.0221(17) 0.026(2) 0.0270(17) -0.0036(19) -0.0088(14) 0.0046(19) N3 0.0220(18) 0.031(2) 0.0252(17) -0.0070(19) -0.0078(14) 0.003(2) N4 0.022(2) 0.015(2) 0.0212(17) 0.0006(15) -0.0032(15) -0.0018(15) O1 0.0190(16) 0.0201(17) 0.0269(15) -0.0028(13) -0.0094(13) 0.0015(12) O2 0.0337(18) 0.0139(17) 0.0251(15) -0.0002(14) -0.0001(13) -0.0014(14) O3 0.0297(17) 0.0171(17) 0.0304(16) -0.0045(14) 0.0037(14) -0.0069(14) S1 0.0299(6) 0.0134(6) 0.0315(5) 0.0001(6) -0.0132(4) 0.0003(6) O11 0.0368(19) 0.0266(19) 0.109(3) -0.007(2) -0.0307(19) 0.0016(18) O12 0.0340(19) 0.0156(17) 0.0340(16) 0.0037(13) -0.0064(14) 0.0028(13) O13 0.0359(18) 0.0160(17) 0.0274(15) -0.0043(13) 0.0020(14) -0.0038(13) O14 0.100(3) 0.0209(19) 0.0235(16) -0.0032(14) -0.0007(18) -0.0050(17) O21 0.065(3) 0.049(2) 0.039(2) -0.0160(19) -0.0064(19) 0.0103(19) O22 0.121(4) 0.108(4) 0.087(3) 0.001(3) 0.027(3) 0.038(3) O23 0.255(10) 0.163(8) 0.386(13) -0.011(8) -0.060(9) 0.032(7) O24 0.20(3) 0.47(3) 0.147(16) -0.13(2) -0.022(15) 0.17(2) O25 0.141(16) 0.128(15) 0.51(4) 0.06(2) -0.01(3) -0.032(11) O26 0.160(14) 0.123(12) 0.175(12) 0.059(10) 0.000(11) -0.027(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 Co1 O13 2.061(3) . ? Co1 O13 2.061(3) 5_656 ? Co1 O2 2.097(3) . ? Co1 O2 2.097(3) 5_656 ? Co1 N1 2.176(3) . ? Co1 N1 2.176(3) 5_656 ? Co2 O12 2.081(3) 5_666 ? Co2 O12 2.081(3) . ? Co2 O3 2.082(3) . ? Co2 O3 2.082(3) 5_666 ? Co2 N4 2.145(3) 3 ? Co2 N4 2.145(3) 7 ? C1 N1 1.344(5) . ? C1 C2 1.379(5) . ? C2 C3 1.386(5) . ? C3 C4 1.396(5) . ? C3 C6 1.465(5) . ? C4 C5 1.373(5) . ? C5 N1 1.344(5) . ? C6 N2 1.289(5) . ? C6 O1 1.366(4) . ? C7 N3 1.295(5) . ? C7 O1 1.365(4) . ? C7 C10 1.458(5) . ? C8 N4 1.342(4) . ? C8 C9 1.389(5) . ? C9 C10 1.392(5) . ? C10 C11 1.384(5) . ? C11 C12 1.382(5) . ? C12 N4 1.338(5) . ? C13 O2 1.454(5) . ? C14 O3 1.439(5) . ? C22 O22 1.421(6) . ? N2 N3 1.406(4) . ? N4 Co2 2.145(3) 3_444 ? S1 O14 1.456(3) . ? S1 O12 1.461(3) . ? S1 O11 1.467(3) . ? S1 O13 1.482(3) . ? O24 O24 0.88(5) 2_656 ? O24 O25 1.39(3) . ? O25 O26 1.73(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 O13 Co1 O13 180.0 . 5_656 ? O13 Co1 O2 89.80(10) . . ? O13 Co1 O2 90.20(10) 5_656 . ? O13 Co1 O2 90.20(10) . 5_656 ? O13 Co1 O2 89.80(10) 5_656 5_656 ? O2 Co1 O2 180.0 . 5_656 ? O13 Co1 N1 86.87(11) . . ? O13 Co1 N1 93.13(11) 5_656 . ? O2 Co1 N1 89.02(11) . . ? O2 Co1 N1 90.98(11) 5_656 . ? O13 Co1 N1 93.13(11) . 5_656 ? O13 Co1 N1 86.87(11) 5_656 5_656 ? O2 Co1 N1 90.98(11) . 5_656 ? O2 Co1 N1 89.02(11) 5_656 5_656 ? N1 Co1 N1 180.0 . 5_656 ? O12 Co2 O12 180.00(14) 5_666 . ? O12 Co2 O3 90.47(11) 5_666 . ? O12 Co2 O3 89.53(11) . . ? O12 Co2 O3 89.53(11) 5_666 5_666 ? O12 Co2 O3 90.47(11) . 5_666 ? O3 Co2 O3 180.0 . 5_666 ? O12 Co2 N4 85.43(11) 5_666 3 ? O12 Co2 N4 94.57(11) . 3 ? O3 Co2 N4 91.55(11) . 3 ? O3 Co2 N4 88.45(11) 5_666 3 ? O12 Co2 N4 94.57(11) 5_666 7 ? O12 Co2 N4 85.43(11) . 7 ? O3 Co2 N4 88.45(11) . 7 ? O3 Co2 N4 91.55(11) 5_666 7 ? N4 Co2 N4 180.000(1) 3 7 ? N1 C1 C2 124.2(4) . . ? C1 C2 C3 118.3(4) . . ? C2 C3 C4 118.6(4) . . ? C2 C3 C6 121.8(4) . . ? C4 C3 C6 119.6(4) . . ? C5 C4 C3 118.6(4) . . ? N1 C5 C4 124.0(4) . . ? N2 C6 O1 112.9(3) . . ? N2 C6 C3 128.5(4) . . ? O1 C6 C3 118.6(3) . . ? N3 C7 O1 112.0(3) . . ? N3 C7 C10 128.8(4) . . ? O1 C7 C10 119.2(4) . . ? N4 C8 C9 122.8(4) . . ? C8 C9 C10 118.3(4) . . ? C11 C10 C9 119.1(4) . . ? C11 C10 C7 120.8(4) . . ? C9 C10 C7 120.0(4) . . ? C12 C11 C10 118.7(4) . . ? N4 C12 C11 123.1(4) . . ? C1 N1 C5 116.3(3) . . ? C1 N1 Co1 122.2(3) . . ? C5 N1 Co1 121.5(3) . . ? C6 N2 N3 105.8(3) . . ? C7 N3 N2 106.8(3) . . ? C12 N4 C8 118.0(3) . . ? C12 N4 Co2 120.1(3) . 3_444 ? C8 N4 Co2 121.8(3) . 3_444 ? C7 O1 C6 102.6(3) . . ? C13 O2 Co1 124.4(2) . . ? C14 O3 Co2 125.5(2) . . ? O14 S1 O12 110.20(18) . . ? O14 S1 O11 111.6(2) . . ? O12 S1 O11 109.73(18) . . ? O14 S1 O13 109.11(16) . . ? O12 S1 O13 108.44(16) . . ? O11 S1 O13 107.67(18) . . ? S1 O12 Co2 160.55(19) . . ? S1 O13 Co1 138.74(16) . . ? O24 O24 O25 109(3) 2_656 . ? O24 O25 O26 171.9(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 1.2(6) . . . . ? C1 C2 C3 C4 -0.8(6) . . . . ? C1 C2 C3 C6 178.8(4) . . . . ? C2 C3 C4 C5 0.0(6) . . . . ? C6 C3 C4 C5 -179.6(4) . . . . ? C3 C4 C5 N1 0.6(6) . . . . ? C2 C3 C6 N2 -168.8(4) . . . . ? C4 C3 C6 N2 10.8(6) . . . . ? C2 C3 C6 O1 8.8(5) . . . . ? C4 C3 C6 O1 -171.6(3) . . . . ? N4 C8 C9 C10 0.7(6) . . . . ? C8 C9 C10 C11 -0.4(6) . . . . ? C8 C9 C10 C7 177.2(3) . . . . ? N3 C7 C10 C11 168.6(4) . . . . ? O1 C7 C10 C11 -8.6(5) . . . . ? N3 C7 C10 C9 -8.9(6) . . . . ? O1 C7 C10 C9 173.9(3) . . . . ? C9 C10 C11 C12 -0.6(6) . . . . ? C7 C10 C11 C12 -178.2(3) . . . . ? C10 C11 C12 N4 1.4(6) . . . . ? C2 C1 N1 C5 -0.6(6) . . . . ? C2 C1 N1 Co1 178.6(3) . . . . ? C4 C5 N1 C1 -0.2(6) . . . . ? C4 C5 N1 Co1 -179.5(3) . . . . ? O13 Co1 N1 C1 138.4(3) . . . . ? O13 Co1 N1 C1 -41.6(3) 5_656 . . . ? O2 Co1 N1 C1 -131.8(3) . . . . ? O2 Co1 N1 C1 48.2(3) 5_656 . . . ? N1 Co1 N1 C1 -14(100) 5_656 . . . ? O13 Co1 N1 C5 -42.4(3) . . . . ? O13 Co1 N1 C5 137.6(3) 5_656 . . . ? O2 Co1 N1 C5 47.5(3) . . . . ? O2 Co1 N1 C5 -132.5(3) 5_656 . . . ? N1 Co1 N1 C5 165(100) 5_656 . . . ? O1 C6 N2 N3 0.1(4) . . . . ? C3 C6 N2 N3 177.8(4) . . . . ? O1 C7 N3 N2 0.5(4) . . . . ? C10 C7 N3 N2 -176.9(4) . . . . ? C6 N2 N3 C7 -0.3(4) . . . . ? C11 C12 N4 C8 -1.1(6) . . . . ? C11 C12 N4 Co2 -178.9(3) . . . 3_444 ? C9 C8 N4 C12 0.0(6) . . . . ? C9 C8 N4 Co2 177.7(3) . . . 3_444 ? N3 C7 O1 C6 -0.4(4) . . . . ? C10 C7 O1 C6 177.2(3) . . . . ? N2 C6 O1 C7 0.2(4) . . . . ? C3 C6 O1 C7 -177.8(3) . . . . ? O13 Co1 O2 C13 -141.9(3) . . . . ? O13 Co1 O2 C13 38.1(3) 5_656 . . . ? O2 Co1 O2 C13 13(100) 5_656 . . . ? N1 Co1 O2 C13 131.2(3) . . . . ? N1 Co1 O2 C13 -48.8(3) 5_656 . . . ? O12 Co2 O3 C14 145.6(3) 5_666 . . . ? O12 Co2 O3 C14 -34.4(3) . . . . ? O3 Co2 O3 C14 -138(100) 5_666 . . . ? N4 Co2 O3 C14 -128.9(3) 3 . . . ? N4 Co2 O3 C14 51.1(3) 7 . . . ? O14 S1 O12 Co2 109.0(5) . . . . ? O11 S1 O12 Co2 -14.3(6) . . . . ? O13 S1 O12 Co2 -131.7(5) . . . . ? O12 Co2 O12 S1 44(100) 5_666 . . . ? O3 Co2 O12 S1 -119.6(5) . . . . ? O3 Co2 O12 S1 60.4(5) 5_666 . . . ? N4 Co2 O12 S1 -28.1(5) 3 . . . ? N4 Co2 O12 S1 151.9(5) 7 . . . ? O14 S1 O13 Co1 -17.0(3) . . . . ? O12 S1 O13 Co1 -137.1(2) . . . . ? O11 S1 O13 Co1 104.3(3) . . . . ? O13 Co1 O13 S1 -108.1(3) 5_656 . . . ? O2 Co1 O13 S1 18.7(3) . . . . ? O2 Co1 O13 S1 -161.3(3) 5_656 . . . ? N1 Co1 O13 S1 107.7(3) . . . . ? N1 Co1 O13 S1 -72.3(3) 5_656 . . . ? O24 O24 O25 O26 -40(15) 2_656 . . . ? 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 O22 H22A O11 0.99 1.82 2.797(5) 170.4 . O21 H21B O14 0.880(19) 2.02(2) 2.846(5) 156(5) 4_556 O21 H21A O22 0.908(19) 1.87(2) 2.736(6) 159(4) 5_666 O3 H3A O21 0.858(18) 1.76(2) 2.609(4) 168(4) . O2 H2A O14 0.882(18) 1.82(2) 2.688(4) 168(4) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.966 _refine_diff_density_min -0.640 _refine_diff_density_rms 0.080 data_compound_3 _database_code_CSD 193470 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C49 H42 Cl2 Cu N16 O16' _chemical_formula_weight 1245.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.4658(7) _cell_length_b 12.1314(7) _cell_length_c 17.8301(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.1820(10) _cell_angle_gamma 90.00 _cell_volume 2653.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150.0(2) _cell_measurement_reflns_used 5612 _cell_measurement_theta_min 2.187 _cell_measurement_theta_max 26.373 _exptl_crystal_description bar _exptl_crystal_colour 'deep blue' _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1278 _exptl_absorpt_coefficient_mu 0.600 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4833 _exptl_absorpt_correction_T_max 0.8943 _exptl_absorpt_process_details '(SADABS, Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(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 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 17222 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0547 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 26.38 _reflns_number_total 5421 _reflns_number_gt 4147 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART NT V5.625 (Bruker, 2000)' _computing_cell_refinement 'SAINT+ NT V6.02a (Bruker, 1998)' _computing_data_reduction 'SAINT+ NT V6.02a' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V5.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL V5.1' _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^)+(0.0603P)^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 5421 _refine_ls_number_parameters 405 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1137 _refine_ls_wR_factor_gt 0.1109 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _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 0.0000 0.0000 0.5000 0.01968(12) Uani 1 2 d S . . C1 C -0.10183(17) 0.13553(18) 0.36575(12) 0.0188(5) Uani 1 1 d . . . H1 H -0.1683 0.1045 0.3750 0.023 Uiso 1 1 calc R . . C2 C -0.10450(18) 0.20208(18) 0.30237(13) 0.0198(5) Uani 1 1 d . . . H2 H -0.1715 0.2180 0.2696 0.024 Uiso 1 1 calc R . . C3 C -0.00671(18) 0.24522(18) 0.28769(13) 0.0192(5) Uani 1 1 d . . . C4 C 0.08796(18) 0.22740(19) 0.34045(13) 0.0229(5) Uani 1 1 d . . . H4 H 0.1550 0.2596 0.3335 0.027 Uiso 1 1 calc R . . C5 C 0.08286(19) 0.16221(19) 0.40298(13) 0.0236(5) Uani 1 1 d . . . H5 H 0.1475 0.1517 0.4394 0.028 Uiso 1 1 calc R . . C6 C 0.00046(18) 0.30396(19) 0.21692(13) 0.0201(5) Uani 1 1 d . . . C7 C 0.08189(18) 0.36709(19) 0.13180(13) 0.0205(5) Uani 1 1 d . . . C8 C 0.36390(19) 0.3710(2) 0.08796(14) 0.0245(5) Uani 1 1 d . . . H8 H 0.4326 0.3382 0.1068 0.029 Uiso 1 1 calc R . . C9 C 0.27703(19) 0.3442(2) 0.12266(14) 0.0250(5) Uani 1 1 d . . . H9 H 0.2860 0.2946 0.1646 0.030 Uiso 1 1 calc R . . C10 C 0.17592(18) 0.39111(19) 0.09512(13) 0.0213(5) Uani 1 1 d . . . C11 C 0.16572(18) 0.46065(19) 0.03215(13) 0.0213(5) Uani 1 1 d . . . H11 H 0.0971 0.4919 0.0110 0.026 Uiso 1 1 calc R . . C12 C 0.25695(18) 0.48338(19) 0.00098(13) 0.0213(5) Uani 1 1 d . . . H12 H 0.2496 0.5308 -0.0420 0.026 Uiso 1 1 calc R . . N1 N -0.00948(14) 0.11260(15) 0.41499(10) 0.0190(4) Uani 1 1 d . . . N2 N -0.07428(16) 0.34789(17) 0.16637(11) 0.0250(5) Uani 1 1 d . . . N3 N -0.01994(16) 0.39069(17) 0.10965(11) 0.0257(5) Uani 1 1 d . . . N4 N 0.35681(14) 0.44097(15) 0.02909(10) 0.0196(4) Uani 1 1 d . . . O1 O 0.10147(12) 0.31228(13) 0.19896(9) 0.0222(4) Uani 1 1 d . . . C13 C 0.4410(2) 0.5564(2) 0.73016(15) 0.0329(6) Uani 1 1 d . . . H13 H 0.5078 0.5878 0.7548 0.039 Uiso 1 1 calc R . . C14 C 0.4425(2) 0.4928(2) 0.66596(14) 0.0283(6) Uani 1 1 d . . . H14 H 0.5083 0.4809 0.6472 0.034 Uiso 1 1 calc R . . C15 C 0.34414(19) 0.4466(2) 0.62934(14) 0.0264(5) Uani 1 1 d . . . C16 C 0.2497(2) 0.4674(2) 0.65832(15) 0.0317(6) Uani 1 1 d . . . H16 H 0.1816 0.4382 0.6342 0.038 Uiso 1 1 calc R . . C17 C 0.2574(2) 0.5316(2) 0.72320(15) 0.0343(6) Uani 1 1 d . . . H17 H 0.1928 0.5449 0.7432 0.041 Uiso 1 1 calc R . . C18 C 0.34192(19) 0.3759(2) 0.56302(14) 0.0253(5) Uani 1 1 d . . . C19 C 0.40513(19) 0.2926(2) 0.47527(13) 0.0248(5) Uani 1 1 d . . . C20 C 0.6677(2) 0.2548(2) 0.40534(15) 0.0288(6) Uani 1 1 d . . . H20 H 0.7415 0.2778 0.4189 0.035 Uiso 1 1 calc R . . C21 C 0.59418(19) 0.2927(2) 0.44942(14) 0.0256(5) Uani 1 1 d . . . H21 H 0.6168 0.3401 0.4917 0.031 Uiso 1 1 calc R . . C22 C 0.48624(18) 0.25920(19) 0.42963(14) 0.0238(5) Uani 1 1 d . . . C23 C 0.4567(2) 0.1920(2) 0.36611(14) 0.0290(6) Uani 1 1 d . . . H23 H 0.3832 0.1695 0.3504 0.035 Uiso 1 1 calc R . . C24 C 0.5369(2) 0.1586(2) 0.32634(15) 0.0312(6) Uani 1 1 d . . . H24 H 0.5163 0.1121 0.2833 0.037 Uiso 1 1 calc R . . N5 N 0.35161(19) 0.57639(18) 0.75973(12) 0.0359(5) Uani 1 1 d . . . N6 N 0.26430(17) 0.31345(19) 0.52906(13) 0.0350(5) Uani 1 1 d . . . N7 N 0.30631(16) 0.25847(19) 0.47081(12) 0.0335(5) Uani 1 1 d . . . N8 N 0.64207(17) 0.18791(18) 0.34494(12) 0.0310(5) Uani 1 1 d . . . O2 O 0.43441(13) 0.36713(13) 0.53241(9) 0.0255(4) Uani 1 1 d . . . O3 O 0.11153(14) 0.13634(16) 0.58594(10) 0.0277(4) Uani 1 1 d D . . H3A H 0.127(2) 0.131(3) 0.6327(10) 0.051(10) Uiso 1 1 d D . . H3B H 0.130(3) 0.199(2) 0.574(2) 0.107(17) Uiso 1 1 d D . . Cl Cl 0.75991(6) 0.48290(6) 0.67467(4) 0.0436(2) Uani 1 1 d . . . O11 O 0.7495(2) 0.4052(2) 0.73171(19) 0.1016(11) Uani 1 1 d . . . O12 O 0.7121(3) 0.4385(3) 0.60447(19) 0.1192(14) Uani 1 1 d . . . O13 O 0.87379(19) 0.50343(19) 0.67856(17) 0.0670(7) Uani 1 1 d . . . O14 O 0.70601(17) 0.58322(18) 0.68735(15) 0.0618(7) Uani 1 1 d . . . O1S O 0.9823(6) 0.4967(6) 0.5505(4) 0.107(2) Uani 0.50 1 d PD A -1 H1S H 0.9676 0.4964 0.5947 0.160 Uiso 0.50 1 calc PR A -1 C1S C 0.9453(8) 0.3943(6) 0.5122(5) 0.075(2) Uani 0.50 1 d PD A -1 H1S1 H 0.9648 0.3324 0.5473 0.112 Uiso 0.50 1 calc PR A -1 H1S2 H 0.9802 0.3847 0.4675 0.112 Uiso 0.50 1 calc PR A -1 H1S3 H 0.8660 0.3966 0.4961 0.112 Uiso 0.50 1 calc PR A -1 O2S O 1.0023(5) 0.3608(5) 0.5748(4) 0.097(2) Uani 0.50 1 d P B -2 H2SA H 0.9680 0.3991 0.6027 0.146 Uiso 0.50 1 d PR B -2 H2SB H 0.9641 0.3325 0.5366 0.146 Uiso 0.50 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 0.0180(2) 0.0223(2) 0.0212(2) 0.00661(16) 0.01043(15) 0.00202(16) C1 0.0182(11) 0.0189(12) 0.0212(12) -0.0016(9) 0.0086(9) 0.0000(9) C2 0.0186(11) 0.0209(13) 0.0210(12) 0.0006(9) 0.0065(9) 0.0020(9) C3 0.0228(12) 0.0168(12) 0.0195(12) 0.0002(9) 0.0075(9) 0.0011(9) C4 0.0190(11) 0.0237(13) 0.0273(13) 0.0045(10) 0.0079(9) -0.0041(10) C5 0.0209(12) 0.0260(14) 0.0241(13) 0.0036(10) 0.0051(9) -0.0031(10) C6 0.0200(11) 0.0198(13) 0.0227(12) 0.0005(9) 0.0094(9) -0.0017(9) C7 0.0232(12) 0.0204(13) 0.0195(12) 0.0024(9) 0.0081(9) -0.0013(9) C8 0.0227(12) 0.0254(14) 0.0261(13) 0.0000(10) 0.0063(10) 0.0022(10) C9 0.0261(13) 0.0266(14) 0.0239(13) 0.0054(10) 0.0089(10) 0.0004(10) C10 0.0225(12) 0.0226(13) 0.0204(12) -0.0010(9) 0.0084(9) -0.0016(9) C11 0.0181(11) 0.0257(13) 0.0211(12) 0.0011(9) 0.0059(9) 0.0000(9) C12 0.0231(12) 0.0232(13) 0.0187(12) 0.0002(9) 0.0069(9) 0.0002(9) N1 0.0196(10) 0.0190(10) 0.0199(10) 0.0020(8) 0.0073(8) 0.0002(8) N2 0.0247(11) 0.0301(12) 0.0222(11) 0.0089(8) 0.0097(8) -0.0007(9) N3 0.0243(11) 0.0313(12) 0.0237(11) 0.0085(9) 0.0103(8) -0.0011(9) N4 0.0207(10) 0.0204(11) 0.0197(10) -0.0032(8) 0.0090(7) -0.0011(8) O1 0.0198(8) 0.0273(9) 0.0213(9) 0.0070(7) 0.0085(6) 0.0005(7) C13 0.0423(16) 0.0297(15) 0.0263(14) 0.0028(11) 0.0052(11) -0.0018(12) C14 0.0310(14) 0.0280(14) 0.0263(13) 0.0019(10) 0.0063(10) -0.0013(11) C15 0.0301(13) 0.0245(14) 0.0255(13) 0.0043(10) 0.0075(10) 0.0025(10) C16 0.0314(14) 0.0322(15) 0.0328(15) 0.0036(11) 0.0093(11) 0.0048(11) C17 0.0432(16) 0.0324(15) 0.0314(15) 0.0037(11) 0.0174(12) 0.0098(12) C18 0.0214(12) 0.0284(15) 0.0273(14) 0.0033(10) 0.0075(10) 0.0027(10) C19 0.0256(13) 0.0260(14) 0.0228(13) -0.0002(10) 0.0041(10) -0.0002(10) C20 0.0224(13) 0.0293(15) 0.0358(15) 0.0059(11) 0.0084(10) 0.0012(10) C21 0.0254(13) 0.0225(13) 0.0292(14) 0.0032(10) 0.0057(10) -0.0001(10) C22 0.0247(12) 0.0213(13) 0.0266(13) 0.0037(10) 0.0080(10) 0.0021(10) C23 0.0252(13) 0.0297(15) 0.0323(15) -0.0011(11) 0.0055(10) -0.0016(10) C24 0.0357(15) 0.0288(15) 0.0302(15) -0.0057(11) 0.0092(11) 0.0002(11) N5 0.0535(15) 0.0298(13) 0.0262(12) 0.0021(9) 0.0121(10) 0.0040(11) N6 0.0269(12) 0.0452(15) 0.0342(13) -0.0111(10) 0.0091(9) -0.0019(10) N7 0.0244(11) 0.0447(15) 0.0332(13) -0.0123(10) 0.0095(9) -0.0029(10) N8 0.0290(12) 0.0310(13) 0.0353(13) -0.0002(9) 0.0122(9) 0.0022(9) O2 0.0244(9) 0.0267(10) 0.0269(9) -0.0036(7) 0.0085(7) -0.0025(7) O3 0.0289(10) 0.0321(11) 0.0237(10) -0.0003(8) 0.0092(8) -0.0002(8) Cl 0.0430(4) 0.0346(4) 0.0491(5) 0.0015(3) -0.0025(3) -0.0057(3) O11 0.106(2) 0.078(2) 0.122(3) 0.0556(19) 0.023(2) -0.0007(17) O12 0.106(2) 0.136(3) 0.096(3) -0.066(2) -0.032(2) 0.014(2) O13 0.0483(15) 0.0577(17) 0.095(2) -0.0101(13) 0.0129(13) 0.0044(11) O14 0.0423(13) 0.0414(14) 0.099(2) -0.0004(12) 0.0061(12) 0.0030(10) O1S 0.085(5) 0.156(7) 0.088(5) 0.002(4) 0.038(4) -0.009(4) C1S 0.123(7) 0.045(5) 0.055(5) -0.006(4) 0.012(5) 0.003(5) O2S 0.079(4) 0.068(4) 0.138(6) 0.043(4) 0.002(4) -0.029(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 N1 2.0282(18) . ? Cu N1 2.0282(18) 3_556 ? Cu N4 2.0726(18) 2_545 ? Cu N4 2.0726(18) 4_566 ? Cu O3 2.5027(18) . ? C1 N1 1.348(3) . ? C1 C2 1.384(3) . ? C2 C3 1.393(3) . ? C3 C4 1.390(3) . ? C3 C6 1.466(3) . ? C4 C5 1.378(3) . ? C5 N1 1.349(3) . ? C6 N2 1.291(3) . ? C6 O1 1.357(3) . ? C7 N3 1.293(3) . ? C7 O1 1.354(3) . ? C7 C10 1.469(3) . ? C8 N4 1.340(3) . ? C8 C9 1.378(3) . ? C9 C10 1.391(3) . ? C10 C11 1.392(3) . ? C11 C12 1.379(3) . ? C12 N4 1.358(3) . ? N2 N3 1.412(3) . ? N4 Cu 2.0726(18) 2 ? C13 N5 1.337(3) . ? C13 C14 1.383(4) . ? C14 C15 1.400(3) . ? C15 C16 1.390(3) . ? C15 C18 1.457(3) . ? C16 C17 1.384(4) . ? C17 N5 1.352(3) . ? C18 N6 1.292(3) . ? C18 O2 1.364(3) . ? C19 N7 1.289(3) . ? C19 O2 1.363(3) . ? C19 C22 1.463(3) . ? C20 N8 1.341(3) . ? C20 C21 1.387(3) . ? C21 C22 1.390(3) . ? C22 C23 1.391(3) . ? C23 C24 1.384(3) . ? C24 N8 1.342(3) . ? N6 N7 1.411(3) . ? Cl O12 1.396(3) . ? Cl O11 1.409(3) . ? Cl O14 1.427(2) . ? Cl O13 1.431(2) . ? O1S C1S 1.452(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu N1 180.0 . 3_556 ? N1 Cu N4 89.12(7) . 2_545 ? N1 Cu N4 90.88(7) 3_556 2_545 ? N1 Cu N4 90.88(7) . 4_566 ? N1 Cu N4 89.12(7) 3_556 4_566 ? N4 Cu N4 180.0 2_545 4_566 ? N1 Cu O3 88.00(7) . . ? N1 Cu O3 92.00(7) 3_556 . ? N4 Cu O3 88.38(7) 2_545 . ? N4 Cu O3 91.62(7) 4_566 . ? N1 C1 C2 123.1(2) . . ? C1 C2 C3 118.5(2) . . ? C4 C3 C2 118.7(2) . . ? C4 C3 C6 119.0(2) . . ? C2 C3 C6 122.2(2) . . ? C5 C4 C3 118.8(2) . . ? N1 C5 C4 123.2(2) . . ? N2 C6 O1 112.9(2) . . ? N2 C6 C3 130.9(2) . . ? O1 C6 C3 116.09(19) . . ? N3 C7 O1 113.12(19) . . ? N3 C7 C10 129.6(2) . . ? O1 C7 C10 117.26(19) . . ? N4 C8 C9 123.6(2) . . ? C8 C9 C10 118.7(2) . . ? C9 C10 C11 118.7(2) . . ? C9 C10 C7 120.4(2) . . ? C11 C10 C7 120.9(2) . . ? C12 C11 C10 118.8(2) . . ? N4 C12 C11 122.9(2) . . ? C1 N1 C5 117.32(19) . . ? C1 N1 Cu 123.79(15) . . ? C5 N1 Cu 118.71(15) . . ? C6 N2 N3 105.87(18) . . ? C7 N3 N2 105.62(18) . . ? C8 N4 C12 117.26(19) . . ? C8 N4 Cu 118.31(15) . 2 ? C12 N4 Cu 123.39(15) . 2 ? C7 O1 C6 102.45(17) . . ? N5 C13 C14 124.2(2) . . ? C13 C14 C15 118.1(2) . . ? C16 C15 C14 118.9(2) . . ? C16 C15 C18 120.9(2) . . ? C14 C15 C18 120.3(2) . . ? C17 C16 C15 118.4(2) . . ? N5 C17 C16 123.7(2) . . ? N6 C18 O2 112.5(2) . . ? N6 C18 C15 129.1(2) . . ? O2 C18 C15 118.3(2) . . ? N7 C19 O2 112.7(2) . . ? N7 C19 C22 128.6(2) . . ? O2 C19 C22 118.7(2) . . ? N8 C20 C21 124.6(2) . . ? C20 C21 C22 117.8(2) . . ? C21 C22 C23 118.9(2) . . ? C21 C22 C19 120.7(2) . . ? C23 C22 C19 120.4(2) . . ? C24 C23 C22 118.5(2) . . ? N8 C24 C23 123.9(2) . . ? C13 N5 C17 116.8(2) . . ? C18 N6 N7 106.1(2) . . ? C19 N7 N6 106.1(2) . . ? C20 N8 C24 116.3(2) . . ? C19 O2 C18 102.54(18) . . ? O12 Cl O11 108.1(2) . . ? O12 Cl O14 109.45(17) . . ? O11 Cl O14 110.48(18) . . ? O12 Cl O13 111.9(2) . . ? O11 Cl O13 107.37(17) . . ? O14 Cl O13 109.55(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 1.7(3) . . . . ? C1 C2 C3 C4 -5.3(3) . . . . ? C1 C2 C3 C6 171.7(2) . . . . ? C2 C3 C4 C5 3.9(3) . . . . ? C6 C3 C4 C5 -173.2(2) . . . . ? C3 C4 C5 N1 1.4(4) . . . . ? C4 C3 C6 N2 -165.8(2) . . . . ? C2 C3 C6 N2 17.2(4) . . . . ? C4 C3 C6 O1 16.2(3) . . . . ? C2 C3 C6 O1 -160.7(2) . . . . ? N4 C8 C9 C10 0.5(4) . . . . ? C8 C9 C10 C11 1.9(4) . . . . ? C8 C9 C10 C7 -178.3(2) . . . . ? N3 C7 C10 C9 -170.4(2) . . . . ? O1 C7 C10 C9 9.7(3) . . . . ? N3 C7 C10 C11 9.4(4) . . . . ? O1 C7 C10 C11 -170.5(2) . . . . ? C9 C10 C11 C12 -2.2(3) . . . . ? C7 C10 C11 C12 178.1(2) . . . . ? C10 C11 C12 N4 -0.1(3) . . . . ? C2 C1 N1 C5 3.4(3) . . . . ? C2 C1 N1 Cu -171.64(16) . . . . ? C4 C5 N1 C1 -5.0(3) . . . . ? C4 C5 N1 Cu 170.33(18) . . . . ? N1 Cu N1 C1 106(100) 3_556 . . . ? N4 Cu N1 C1 135.34(18) 2_545 . . . ? N4 Cu N1 C1 -44.66(18) 4_566 . . . ? O3 Cu N1 C1 -136.25(18) . . . . ? N1 Cu N1 C5 -69(100) 3_556 . . . ? N4 Cu N1 C5 -39.68(17) 2_545 . . . ? N4 Cu N1 C5 140.32(17) 4_566 . . . ? O3 Cu N1 C5 48.73(17) . . . . ? O1 C6 N2 N3 -0.6(3) . . . . ? C3 C6 N2 N3 -178.6(2) . . . . ? O1 C7 N3 N2 -0.3(3) . . . . ? C10 C7 N3 N2 179.8(2) . . . . ? C6 N2 N3 C7 0.5(3) . . . . ? C9 C8 N4 C12 -2.7(3) . . . . ? C9 C8 N4 Cu 166.03(19) . . . 2 ? C11 C12 N4 C8 2.5(3) . . . . ? C11 C12 N4 Cu -165.65(17) . . . 2 ? N3 C7 O1 C6 -0.1(3) . . . . ? C10 C7 O1 C6 179.8(2) . . . . ? N2 C6 O1 C7 0.5(2) . . . . ? C3 C6 O1 C7 178.78(19) . . . . ? N5 C13 C14 C15 0.2(4) . . . . ? C13 C14 C15 C16 0.7(4) . . . . ? C13 C14 C15 C18 -177.9(2) . . . . ? C14 C15 C16 C17 -1.1(4) . . . . ? C18 C15 C16 C17 177.5(2) . . . . ? C15 C16 C17 N5 0.7(4) . . . . ? C16 C15 C18 N6 -10.0(4) . . . . ? C14 C15 C18 N6 168.6(3) . . . . ? C16 C15 C18 O2 173.5(2) . . . . ? C14 C15 C18 O2 -7.9(3) . . . . ? N8 C20 C21 C22 0.0(4) . . . . ? C20 C21 C22 C23 -1.5(3) . . . . ? C20 C21 C22 C19 177.7(2) . . . . ? N7 C19 C22 C21 -170.5(3) . . . . ? O2 C19 C22 C21 7.2(3) . . . . ? N7 C19 C22 C23 8.6(4) . . . . ? O2 C19 C22 C23 -173.6(2) . . . . ? C21 C22 C23 C24 1.8(4) . . . . ? C19 C22 C23 C24 -177.4(2) . . . . ? C22 C23 C24 N8 -0.6(4) . . . . ? C14 C13 N5 C17 -0.6(4) . . . . ? C16 C17 N5 C13 0.1(4) . . . . ? O2 C18 N6 N7 -0.3(3) . . . . ? C15 C18 N6 N7 -176.9(2) . . . . ? O2 C19 N7 N6 0.1(3) . . . . ? C22 C19 N7 N6 178.0(2) . . . . ? C18 N6 N7 C19 0.2(3) . . . . ? C21 C20 N8 C24 1.2(4) . . . . ? C23 C24 N8 C20 -0.9(4) . . . . ? N7 C19 O2 C18 -0.2(3) . . . . ? C22 C19 O2 C18 -178.4(2) . . . . ? N6 C18 O2 C19 0.3(3) . . . . ? C15 C18 O2 C19 177.3(2) . . . . ? 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 N5 0.824(18) 2.002(19) 2.804(3) 164(3) 2_546 O3 H3B O2S 0.827(19) 2.53(4) 3.035(7) 120(3) 1_455 O3 H3B N6 0.827(19) 2.42(3) 3.155(3) 148(4) . O1S H1S O13 0.84 2.06 2.854(7) 158.2 . O2S H2SA O13 0.85 2.32 3.167(8) 179.7 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.589 _refine_diff_density_min -1.123 _refine_diff_density_rms 0.081 data_Compound_4 _database_code_CSD 193471 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H24 Cl2 Cu N8 O14' _chemical_formula_weight 782.95 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3841(3) _cell_length_b 11.0490(5) _cell_length_c 20.2981(9) _cell_angle_alpha 94.2320(10) _cell_angle_beta 91.4680(10) _cell_angle_gamma 109.0700(10) _cell_volume 1558.73(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150.0(2) _cell_measurement_reflns_used 9426 _cell_measurement_theta_min 2.278 _cell_measurement_theta_max 26.410 _exptl_crystal_description block _exptl_crystal_colour cyan _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.668 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 798 _exptl_absorpt_coefficient_mu 0.954 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5541 _exptl_absorpt_correction_T_max 0.8677 _exptl_absorpt_process_details '(SADABS, Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(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 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 14436 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0556 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.41 _reflns_number_total 6350 _reflns_number_gt 5008 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART NT V5.625 (Bruker, 2000)' _computing_cell_refinement 'SAINT+ NT V6.02a (Bruker, 1998)' _computing_data_reduction 'SAINT+ NT V6.02a' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V5.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL V5.1' _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^)+(0.0391P)^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 6350 _refine_ls_number_parameters 511 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.0913 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.41674(4) 0.41599(3) 0.240215(15) 0.02102(10) Uani 1 1 d . . . C1 C 0.2440(4) 0.2111(2) 0.32714(14) 0.0298(6) Uani 1 1 d . . . H1 H 0.1981 0.2746 0.3477 0.036 Uiso 1 1 calc R . . C2 C 0.2112(4) 0.0979(2) 0.35589(13) 0.0279(6) Uani 1 1 d . . . H2 H 0.1469 0.0845 0.3960 0.034 Uiso 1 1 calc R . . C3 C 0.2736(4) 0.0037(2) 0.32544(12) 0.0217(5) Uani 1 1 d . . . C4 C 0.3662(4) 0.0272(2) 0.26675(13) 0.0265(6) Uani 1 1 d . . . H4 H 0.4084 -0.0364 0.2442 0.032 Uiso 1 1 calc R . . C5 C 0.3958(4) 0.1444(2) 0.24185(13) 0.0267(6) Uani 1 1 d . . . H5 H 0.4605 0.1606 0.2019 0.032 Uiso 1 1 calc R . . C6 C 0.2492(4) -0.1163(2) 0.35590(12) 0.0210(5) Uani 1 1 d . . . C7 C 0.2271(3) -0.2379(2) 0.43271(12) 0.0203(5) Uani 1 1 d . . . C8 C 0.2372(4) -0.2214(3) 0.61617(14) 0.0338(7) Uani 1 1 d . . . H8 H 0.2435 -0.1600 0.6522 0.041 Uiso 1 1 calc R . . C9 C 0.2359(4) -0.1841(3) 0.55319(13) 0.0285(6) Uani 1 1 d . . . H9 H 0.2409 -0.0991 0.5460 0.034 Uiso 1 1 calc R . . C10 C 0.2273(3) -0.2726(2) 0.50057(12) 0.0219(5) Uani 1 1 d . . . C11 C 0.2199(4) -0.3955(3) 0.51313(14) 0.0273(6) Uani 1 1 d . . . H11 H 0.2147 -0.4585 0.4780 0.033 Uiso 1 1 calc R . . C12 C 0.2204(4) -0.4240(3) 0.57825(14) 0.0312(7) Uani 1 1 d . . . H12 H 0.2135 -0.5087 0.5869 0.037 Uiso 1 1 calc R . . N1 N 0.3375(3) 0.23640(19) 0.27145(10) 0.0221(5) Uani 1 1 d . . . N2 N 0.2219(3) -0.2298(2) 0.32686(10) 0.0263(5) Uani 1 1 d . . . N3 N 0.2060(3) -0.3100(2) 0.37807(11) 0.0257(5) Uani 1 1 d . . . N4 N 0.2299(3) -0.3393(2) 0.62945(11) 0.0323(6) Uani 1 1 d . . . O1 O 0.2541(2) -0.11357(15) 0.42225(8) 0.0198(4) Uani 1 1 d . . . C13 C 0.8530(4) 1.1618(3) -0.09567(14) 0.0327(7) Uani 1 1 d . . . H13 H 0.7851 1.1159 -0.1351 0.039 Uiso 1 1 calc R . . C14 C 0.8247(4) 1.1005(3) -0.03837(13) 0.0292(6) Uani 1 1 d . . . H14 H 0.7392 1.0150 -0.0382 0.035 Uiso 1 1 calc R . . C15 C 0.9239(4) 1.1667(2) 0.01896(12) 0.0230(6) Uani 1 1 d . . . C16 C 1.0493(4) 1.2904(3) 0.01629(14) 0.0300(6) Uani 1 1 d . . . H16 H 1.1220 1.3375 0.0547 0.036 Uiso 1 1 calc R . . C17 C 1.0660(4) 1.3436(3) -0.04382(14) 0.0330(7) Uani 1 1 d . . . H17 H 1.1508 1.4289 -0.0455 0.040 Uiso 1 1 calc R . . C18 C 0.8951(4) 1.1096(2) 0.08236(13) 0.0236(6) Uani 1 1 d . . . C19 C 0.7857(4) 0.9654(2) 0.14781(12) 0.0234(6) Uani 1 1 d . . . C20 C 0.4813(4) 0.6210(2) 0.14709(13) 0.0242(6) Uani 1 1 d . . . H20 H 0.3999 0.5543 0.1170 0.029 Uiso 1 1 calc R . . C21 C 0.5641(4) 0.7406(2) 0.12502(13) 0.0245(6) Uani 1 1 d . . . H21 H 0.5399 0.7560 0.0808 0.029 Uiso 1 1 calc R . . C22 C 0.6834(4) 0.8381(2) 0.16869(12) 0.0220(6) Uani 1 1 d . . . C23 C 0.7110(4) 0.8129(2) 0.23328(13) 0.0266(6) Uani 1 1 d . . . H23 H 0.7886 0.8788 0.2646 0.032 Uiso 1 1 calc R . . C24 C 0.6233(4) 0.6902(2) 0.25126(13) 0.0267(6) Uani 1 1 d . . . H24 H 0.6437 0.6726 0.2954 0.032 Uiso 1 1 calc R . . N5 N 0.9704(3) 1.2821(2) -0.09923(11) 0.0312(5) Uani 1 1 d . . . N6 N 0.9616(3) 1.1606(2) 0.14046(11) 0.0276(5) Uani 1 1 d . . . N7 N 0.8898(3) 1.0661(2) 0.18421(11) 0.0294(5) Uani 1 1 d . . . N8 N 0.5101(3) 0.59438(19) 0.20894(10) 0.0217(5) Uani 1 1 d . . . O2 O 0.7808(2) 0.98483(16) 0.08258(8) 0.0229(4) Uani 1 1 d . . . O3 O 0.3701(3) 0.49662(19) 0.34715(10) 0.0331(5) Uani 1 1 d D . . H3A H 0.298(4) 0.541(3) 0.3528(17) 0.063(12) Uiso 1 1 d D . . H3B H 0.455(4) 0.531(3) 0.3767(13) 0.058(12) Uiso 1 1 d D . . O4 O 0.6826(3) 0.43179(19) 0.26174(10) 0.0278(4) Uani 1 1 d D . . H4A H 0.719(4) 0.405(3) 0.2957(11) 0.047(10) Uiso 1 1 d D . . H4B H 0.778(3) 0.469(3) 0.2418(14) 0.045(10) Uiso 1 1 d D . . O5 O 0.1495(3) 0.39279(18) 0.21503(10) 0.0286(4) Uani 1 1 d D . . H5A H 0.099(5) 0.331(2) 0.1879(14) 0.060(12) Uiso 1 1 d D . . H5B H 0.103(5) 0.448(3) 0.2071(16) 0.056(11) Uiso 1 1 d D . . Cl1 Cl 0.57234(10) 0.30810(6) 0.08538(3) 0.02923(16) Uani 1 1 d . . . O11 O 0.4240(3) 0.32809(17) 0.12548(9) 0.0298(4) Uani 1 1 d . . . O12 O 0.5430(3) 0.17245(19) 0.07838(13) 0.0558(7) Uani 1 1 d . . . O13 O 0.7568(3) 0.37463(18) 0.11710(9) 0.0347(5) Uani 1 1 d . . . O14 O 0.5605(4) 0.3552(3) 0.02274(10) 0.0631(7) Uani 1 1 d . . . Cl2A Cl 0.74503(10) -0.20202(7) 0.43676(4) 0.03890(19) Uani 0.623(11) 1 d P A 2 O21A O 0.8567(9) -0.2393(6) 0.3846(3) 0.0456(15) Uani 0.623(11) 1 d P A 2 O22A O 0.6328(6) -0.1344(4) 0.4020(4) 0.0528(18) Uani 0.623(11) 1 d P A 2 O23A O 0.8685(7) -0.1197(7) 0.4843(3) 0.0605(19) Uani 0.623(11) 1 d P A 2 O24A O 0.619(2) -0.3182(14) 0.4565(7) 0.068(3) Uani 0.623(11) 1 d P A 2 Cl2B Cl 0.74503(10) -0.20202(7) 0.43676(4) 0.03890(19) Uani 0.377(11) 1 d P A 1 O21B O 0.8519(15) -0.1710(17) 0.3861(5) 0.073(4) Uani 0.377(11) 1 d P A 1 O22B O 0.6295(9) -0.1268(6) 0.4581(8) 0.061(4) Uani 0.377(11) 1 d P A 1 O23B O 0.8737(10) -0.1968(12) 0.4989(3) 0.049(3) Uani 0.377(11) 1 d P A 1 O24B O 0.621(4) -0.3306(19) 0.4332(11) 0.063(6) Uani 0.377(11) 1 d P A 1 O6 O 1.0195(3) -0.40643(17) 0.21513(10) 0.0244(4) Uani 1 1 d D . . H6A H 1.073(4) -0.353(2) 0.2447(11) 0.037(9) Uiso 1 1 d D . . H6B H 1.023(4) -0.377(3) 0.1791(10) 0.045(10) Uiso 1 1 d 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 0.02369(18) 0.01322(16) 0.02547(18) 0.00674(12) 0.00026(13) 0.00416(13) C1 0.0355(16) 0.0196(14) 0.0383(16) 0.0087(12) 0.0120(13) 0.0124(12) C2 0.0348(16) 0.0232(14) 0.0288(15) 0.0087(12) 0.0115(12) 0.0116(12) C3 0.0229(14) 0.0155(12) 0.0257(14) 0.0052(10) -0.0006(11) 0.0044(11) C4 0.0371(16) 0.0202(13) 0.0251(14) 0.0026(11) 0.0039(12) 0.0129(12) C5 0.0365(16) 0.0229(14) 0.0218(14) 0.0069(11) 0.0068(12) 0.0097(12) C6 0.0204(13) 0.0182(13) 0.0238(14) 0.0053(10) 0.0004(10) 0.0049(11) C7 0.0190(13) 0.0169(12) 0.0268(14) 0.0075(11) 0.0001(11) 0.0071(10) C8 0.0351(17) 0.0362(17) 0.0286(16) 0.0028(13) -0.0022(13) 0.0101(14) C9 0.0319(16) 0.0258(14) 0.0287(15) 0.0070(12) -0.0007(12) 0.0098(12) C10 0.0154(13) 0.0237(13) 0.0265(14) 0.0079(11) 0.0000(10) 0.0051(11) C11 0.0272(15) 0.0234(14) 0.0326(15) 0.0091(12) 0.0038(12) 0.0085(12) C12 0.0275(15) 0.0306(16) 0.0382(17) 0.0176(13) 0.0014(13) 0.0100(13) N1 0.0257(12) 0.0159(11) 0.0253(12) 0.0057(9) 0.0015(9) 0.0068(9) N2 0.0363(13) 0.0182(11) 0.0252(12) 0.0080(9) 0.0001(10) 0.0091(10) N3 0.0344(13) 0.0186(11) 0.0258(12) 0.0081(9) -0.0008(10) 0.0098(10) N4 0.0301(13) 0.0371(14) 0.0296(13) 0.0146(11) 0.0002(10) 0.0086(11) O1 0.0223(9) 0.0150(8) 0.0219(9) 0.0053(7) 0.0007(7) 0.0050(7) C13 0.0370(17) 0.0302(16) 0.0272(15) 0.0038(12) -0.0035(13) 0.0063(13) C14 0.0300(16) 0.0244(14) 0.0305(15) 0.0053(12) -0.0007(12) 0.0049(12) C15 0.0240(14) 0.0216(13) 0.0246(14) 0.0070(11) 0.0028(11) 0.0078(11) C16 0.0314(16) 0.0260(14) 0.0270(15) 0.0053(12) -0.0030(12) 0.0015(12) C17 0.0350(17) 0.0256(15) 0.0336(16) 0.0115(13) 0.0023(13) 0.0015(13) C18 0.0224(14) 0.0159(12) 0.0303(15) 0.0069(11) 0.0024(11) 0.0021(11) C19 0.0272(14) 0.0202(13) 0.0222(14) 0.0044(11) 0.0005(11) 0.0065(11) C20 0.0260(14) 0.0171(13) 0.0280(15) 0.0032(11) -0.0044(11) 0.0053(11) C21 0.0295(15) 0.0203(13) 0.0228(14) 0.0058(11) -0.0022(11) 0.0063(11) C22 0.0231(14) 0.0160(12) 0.0270(14) 0.0045(11) 0.0023(11) 0.0061(11) C23 0.0323(15) 0.0163(13) 0.0269(14) 0.0014(11) -0.0031(12) 0.0026(12) C24 0.0331(16) 0.0187(13) 0.0267(15) 0.0070(11) 0.0000(12) 0.0054(12) N5 0.0342(14) 0.0306(13) 0.0292(13) 0.0117(11) 0.0030(11) 0.0093(11) N6 0.0336(13) 0.0174(11) 0.0272(13) 0.0097(10) 0.0005(10) 0.0006(10) N7 0.0375(14) 0.0179(11) 0.0283(13) 0.0081(10) -0.0003(10) 0.0020(10) N8 0.0234(11) 0.0148(10) 0.0265(12) 0.0038(9) -0.0008(9) 0.0056(9) O2 0.0271(10) 0.0151(9) 0.0237(10) 0.0055(7) 0.0011(8) 0.0023(8) O3 0.0429(13) 0.0260(11) 0.0340(12) 0.0044(9) 0.0062(11) 0.0156(10) O4 0.0232(11) 0.0315(11) 0.0294(11) 0.0166(9) 0.0017(9) 0.0069(9) O5 0.0249(11) 0.0163(10) 0.0433(13) -0.0005(9) -0.0043(9) 0.0063(9) Cl1 0.0338(4) 0.0226(3) 0.0250(3) -0.0002(3) 0.0046(3) 0.0009(3) O11 0.0343(11) 0.0284(10) 0.0291(10) 0.0028(8) 0.0014(8) 0.0136(9) O12 0.0411(13) 0.0214(11) 0.0966(19) -0.0149(12) 0.0202(13) 0.0022(10) O13 0.0303(11) 0.0314(11) 0.0347(11) 0.0019(9) 0.0003(9) -0.0001(9) O14 0.0606(16) 0.0851(19) 0.0228(12) 0.0128(12) -0.0036(11) -0.0054(14) Cl2A 0.0233(4) 0.0354(4) 0.0551(5) -0.0084(4) -0.0009(3) 0.0086(3) O21A 0.032(2) 0.062(4) 0.041(3) -0.017(3) -0.0067(18) 0.019(3) O22A 0.037(2) 0.036(2) 0.087(5) 0.001(2) -0.007(2) 0.0155(18) O23A 0.056(3) 0.079(4) 0.039(3) -0.031(3) -0.009(2) 0.021(3) O24A 0.043(4) 0.074(8) 0.089(8) 0.038(6) 0.012(5) 0.014(5) Cl2B 0.0233(4) 0.0354(4) 0.0551(5) -0.0084(4) -0.0009(3) 0.0086(3) O21B 0.031(4) 0.142(12) 0.041(5) 0.030(7) 0.012(3) 0.016(7) O22B 0.030(4) 0.026(3) 0.131(12) 0.000(4) 0.010(4) 0.014(3) O23B 0.033(4) 0.082(7) 0.034(4) 0.003(4) -0.006(3) 0.025(4) O24B 0.062(8) 0.020(5) 0.095(15) -0.014(8) -0.013(10) 0.003(5) O6 0.0310(11) 0.0186(10) 0.0217(11) 0.0049(9) -0.0026(9) 0.0051(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O4 1.9487(19) . ? Cu O5 1.954(2) . ? Cu N8 2.020(2) . ? Cu N1 2.032(2) . ? Cu O3 2.362(2) . ? Cu O11 2.4651(18) . ? C1 N1 1.339(3) . ? C1 C2 1.371(3) . ? C2 C3 1.381(3) . ? C3 C4 1.388(4) . ? C3 C6 1.465(3) . ? C4 C5 1.378(3) . ? C5 N1 1.337(3) . ? C6 N2 1.297(3) . ? C6 O1 1.344(3) . ? C7 N3 1.292(3) . ? C7 O1 1.355(3) . ? C7 C10 1.457(3) . ? C8 N4 1.334(4) . ? C8 C9 1.372(4) . ? C9 C10 1.380(4) . ? C10 C11 1.384(3) . ? C11 C12 1.381(4) . ? C12 N4 1.330(4) . ? N2 N3 1.397(3) . ? C13 N5 1.338(3) . ? C13 C14 1.375(4) . ? C14 C15 1.381(4) . ? C15 C16 1.384(4) . ? C15 C18 1.465(3) . ? C16 C17 1.384(4) . ? C17 N5 1.326(3) . ? C18 N6 1.281(3) . ? C18 O2 1.361(3) . ? C19 N7 1.291(3) . ? C19 O2 1.358(3) . ? C19 C22 1.462(3) . ? C20 N8 1.338(3) . ? C20 C21 1.376(3) . ? C21 C22 1.386(3) . ? C22 C23 1.384(3) . ? C23 C24 1.379(3) . ? C24 N8 1.344(3) . ? N6 N7 1.400(3) . ? Cl1 O14 1.420(2) . ? Cl1 O13 1.4287(19) . ? Cl1 O12 1.438(2) . ? Cl1 O11 1.4451(19) . ? Cl2A O23A 1.369(4) . ? Cl2A O24A 1.411(15) . ? Cl2A O21A 1.475(6) . ? Cl2A O22A 1.481(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 O4 Cu O5 176.94(9) . . ? O4 Cu N8 88.75(8) . . ? O5 Cu N8 92.52(8) . . ? O4 Cu N1 88.28(8) . . ? O5 Cu N1 90.41(8) . . ? N8 Cu N1 176.91(8) . . ? O4 Cu O3 93.57(8) . . ? O5 Cu O3 89.17(8) . . ? N8 Cu O3 91.88(8) . . ? N1 Cu O3 89.15(8) . . ? O4 Cu O11 93.39(7) . . ? O5 Cu O11 83.87(8) . . ? N8 Cu O11 88.61(7) . . ? N1 Cu O11 90.72(7) . . ? O3 Cu O11 173.04(7) . . ? N1 C1 C2 123.2(2) . . ? C1 C2 C3 118.8(2) . . ? C2 C3 C4 118.7(2) . . ? C2 C3 C6 120.6(2) . . ? C4 C3 C6 120.7(2) . . ? C5 C4 C3 118.7(2) . . ? N1 C5 C4 122.8(2) . . ? N2 C6 O1 113.3(2) . . ? N2 C6 C3 128.2(2) . . ? O1 C6 C3 118.5(2) . . ? N3 C7 O1 112.3(2) . . ? N3 C7 C10 129.0(2) . . ? O1 C7 C10 118.7(2) . . ? N4 C8 C9 123.5(3) . . ? C8 C9 C10 118.6(3) . . ? C9 C10 C11 118.9(2) . . ? C9 C10 C7 120.9(2) . . ? C11 C10 C7 120.2(2) . . ? C12 C11 C10 118.1(3) . . ? N4 C12 C11 123.6(3) . . ? C5 N1 C1 117.7(2) . . ? C5 N1 Cu 121.32(17) . . ? C1 N1 Cu 120.51(17) . . ? C6 N2 N3 105.3(2) . . ? C7 N3 N2 106.6(2) . . ? C12 N4 C8 117.3(2) . . ? C6 O1 C7 102.62(19) . . ? N5 C13 C14 123.9(3) . . ? C13 C14 C15 118.2(3) . . ? C14 C15 C16 119.0(2) . . ? C14 C15 C18 121.2(2) . . ? C16 C15 C18 119.8(2) . . ? C15 C16 C17 118.2(3) . . ? N5 C17 C16 123.7(3) . . ? N6 C18 O2 112.4(2) . . ? N6 C18 C15 129.3(2) . . ? O2 C18 C15 118.3(2) . . ? N7 C19 O2 112.9(2) . . ? N7 C19 C22 127.8(2) . . ? O2 C19 C22 119.2(2) . . ? N8 C20 C21 123.0(2) . . ? C20 C21 C22 118.6(2) . . ? C23 C22 C21 119.0(2) . . ? C23 C22 C19 119.2(2) . . ? C21 C22 C19 121.8(2) . . ? C24 C23 C22 118.6(2) . . ? N8 C24 C23 122.8(2) . . ? C17 N5 C13 116.9(2) . . ? C18 N6 N7 106.9(2) . . ? C19 N7 N6 105.5(2) . . ? C20 N8 C24 117.9(2) . . ? C20 N8 Cu 124.10(17) . . ? C24 N8 Cu 117.74(17) . . ? C19 O2 C18 102.26(19) . . ? O14 Cl1 O13 109.47(13) . . ? O14 Cl1 O12 110.92(16) . . ? O13 Cl1 O12 109.39(13) . . ? O14 Cl1 O11 109.21(14) . . ? O13 Cl1 O11 109.99(11) . . ? O12 Cl1 O11 107.84(12) . . ? Cl1 O11 Cu 134.36(11) . . ? O23A Cl2A O24A 117.6(6) . . ? O23A Cl2A O21A 109.2(3) . . ? O24A Cl2A O21A 105.8(6) . . ? O23A Cl2A O22A 110.2(3) . . ? O24A Cl2A O22A 109.1(7) . . ? O21A Cl2A O22A 104.0(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -1.5(4) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C1 C2 C3 C6 177.3(3) . . . . ? C2 C3 C4 C5 1.3(4) . . . . ? C6 C3 C4 C5 -176.3(2) . . . . ? C3 C4 C5 N1 -0.7(4) . . . . ? C2 C3 C6 N2 148.6(3) . . . . ? C4 C3 C6 N2 -33.9(4) . . . . ? C2 C3 C6 O1 -31.2(4) . . . . ? C4 C3 C6 O1 146.3(2) . . . . ? N4 C8 C9 C10 -0.2(4) . . . . ? C8 C9 C10 C11 0.1(4) . . . . ? C8 C9 C10 C7 -179.5(2) . . . . ? N3 C7 C10 C9 -174.5(3) . . . . ? O1 C7 C10 C9 6.3(4) . . . . ? N3 C7 C10 C11 5.8(4) . . . . ? O1 C7 C10 C11 -173.4(2) . . . . ? C9 C10 C11 C12 0.4(4) . . . . ? C7 C10 C11 C12 -180.0(2) . . . . ? C10 C11 C12 N4 -0.9(4) . . . . ? C4 C5 N1 C1 -1.0(4) . . . . ? C4 C5 N1 Cu 171.3(2) . . . . ? C2 C1 N1 C5 2.1(4) . . . . ? C2 C1 N1 Cu -170.3(2) . . . . ? O4 Cu N1 C5 -61.6(2) . . . . ? O5 Cu N1 C5 115.6(2) . . . . ? N8 Cu N1 C5 -45.8(16) . . . . ? O3 Cu N1 C5 -155.2(2) . . . . ? O11 Cu N1 C5 31.8(2) . . . . ? O4 Cu N1 C1 110.5(2) . . . . ? O5 Cu N1 C1 -72.3(2) . . . . ? N8 Cu N1 C1 126.4(15) . . . . ? O3 Cu N1 C1 16.9(2) . . . . ? O11 Cu N1 C1 -156.1(2) . . . . ? O1 C6 N2 N3 0.4(3) . . . . ? C3 C6 N2 N3 -179.4(2) . . . . ? O1 C7 N3 N2 0.7(3) . . . . ? C10 C7 N3 N2 -178.5(2) . . . . ? C6 N2 N3 C7 -0.7(3) . . . . ? C11 C12 N4 C8 0.8(4) . . . . ? C9 C8 N4 C12 -0.2(4) . . . . ? N2 C6 O1 C7 0.0(3) . . . . ? C3 C6 O1 C7 179.9(2) . . . . ? N3 C7 O1 C6 -0.5(3) . . . . ? C10 C7 O1 C6 178.8(2) . . . . ? N5 C13 C14 C15 -0.3(4) . . . . ? C13 C14 C15 C16 -1.0(4) . . . . ? C13 C14 C15 C18 177.5(2) . . . . ? C14 C15 C16 C17 1.6(4) . . . . ? C18 C15 C16 C17 -176.9(3) . . . . ? C15 C16 C17 N5 -0.9(4) . . . . ? C14 C15 C18 N6 -173.4(3) . . . . ? C16 C15 C18 N6 5.1(4) . . . . ? C14 C15 C18 O2 5.9(4) . . . . ? C16 C15 C18 O2 -175.6(2) . . . . ? N8 C20 C21 C22 0.2(4) . . . . ? C20 C21 C22 C23 -1.8(4) . . . . ? C20 C21 C22 C19 176.2(2) . . . . ? N7 C19 C22 C23 -7.1(4) . . . . ? O2 C19 C22 C23 170.6(2) . . . . ? N7 C19 C22 C21 174.9(3) . . . . ? O2 C19 C22 C21 -7.4(4) . . . . ? C21 C22 C23 C24 2.1(4) . . . . ? C19 C22 C23 C24 -176.0(2) . . . . ? C22 C23 C24 N8 -0.9(4) . . . . ? C16 C17 N5 C13 -0.4(4) . . . . ? C14 C13 N5 C17 1.1(4) . . . . ? O2 C18 N6 N7 0.0(3) . . . . ? C15 C18 N6 N7 179.3(3) . . . . ? O2 C19 N7 N6 -0.3(3) . . . . ? C22 C19 N7 N6 177.5(2) . . . . ? C18 N6 N7 C19 0.2(3) . . . . ? C21 C20 N8 C24 1.0(4) . . . . ? C21 C20 N8 Cu -172.58(19) . . . . ? C23 C24 N8 C20 -0.7(4) . . . . ? C23 C24 N8 Cu 173.3(2) . . . . ? O4 Cu N8 C20 119.2(2) . . . . ? O5 Cu N8 C20 -58.0(2) . . . . ? N1 Cu N8 C20 103.3(15) . . . . ? O3 Cu N8 C20 -147.3(2) . . . . ? O11 Cu N8 C20 25.8(2) . . . . ? O4 Cu N8 C24 -54.42(19) . . . . ? O5 Cu N8 C24 128.36(19) . . . . ? N1 Cu N8 C24 -70.3(16) . . . . ? O3 Cu N8 C24 39.1(2) . . . . ? O11 Cu N8 C24 -147.84(19) . . . . ? N7 C19 O2 C18 0.3(3) . . . . ? C22 C19 O2 C18 -177.7(2) . . . . ? N6 C18 O2 C19 -0.2(3) . . . . ? C15 C18 O2 C19 -179.5(2) . . . . ? O14 Cl1 O11 Cu -132.70(16) . . . . ? O13 Cl1 O11 Cu -12.55(19) . . . . ? O12 Cl1 O11 Cu 106.68(17) . . . . ? O4 Cu O11 Cl1 -6.15(16) . . . . ? O5 Cu O11 Cl1 175.20(16) . . . . ? N8 Cu O11 Cl1 82.51(16) . . . . ? N1 Cu O11 Cl1 -94.47(16) . . . . ? O3 Cu O11 Cl1 176.6(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 O4 H4B O13 0.822(14) 2.65(3) 3.058(3) 113(3) . O3 H3A N3 0.836(14) 2.016(19) 2.821(3) 161(4) 1_565 O3 H3B O24B 0.829(14) 1.90(3) 2.68(2) 156(4) 1_565 O3 H3B O24A 0.829(14) 2.25(2) 3.024(14) 156(3) 1_565 O4 H4B O6 0.822(14) 1.982(17) 2.782(3) 164(3) 1_565 O4 H4A N4 0.840(14) 1.815(15) 2.651(3) 173(3) 2_656 O5 H5A N6 0.822(14) 1.984(17) 2.791(3) 167(3) 1_445 O5 H5B O6 0.815(14) 1.899(17) 2.690(3) 163(3) 1_465 O6 H6A N2 0.807(14) 2.105(15) 2.907(3) 173(3) 1_655 O6 H6B N5 0.823(14) 1.984(15) 2.801(3) 172(3) 2_765 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.740 _refine_diff_density_min -0.614 _refine_diff_density_rms 0.077