# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_CCDC888198 _database_code_depnum_ccdc_archive 'CCDC 888198' #TrackingRef '17090_web_deposit_cif_file_0_YanmeiChen_1358857669.CCDC 888198.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C49 H32 Cl4 Co2 N12, 2(C2 H6 O)' _chemical_formula_sum 'C53 H44 Cl4 Co2 N12 O2' _chemical_formula_weight 1140.66 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' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.935(3) _cell_length_b 14.5352(15) _cell_length_c 17.7035(19) _cell_angle_alpha 90.00 _cell_angle_beta 131.687(2) _cell_angle_gamma 90.00 _cell_volume 4791.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2827 _cell_measurement_theta_min 3.198 _cell_measurement_theta_max 25.055 _exptl_crystal_description rod _exptl_crystal_colour brown _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2336 _exptl_absorpt_coefficient_mu 0.974 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7928 _exptl_absorpt_correction_T_max 0.8757 _exptl_absorpt_process_details 'SADABS (Bruker, 2005)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15882 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4194 _reflns_number_gt 3265 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX-II (Bruker, 2005)' _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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. During the refinement, the command 'omit -2 50' was used to omit the weak reflections above 50 degree. The large residual electron density is colsed to Cl2 atom. ; _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^)+(0.0722P)^2^+23.0914P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4194 _refine_ls_number_parameters 333 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0709 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1439 _refine_ls_wR_factor_gt 0.1319 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.036 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 1.0000 0.53325(5) 0.2500 0.0189(2) Uani 1 2 d S . . N3 N 0.93869(17) 0.3708(2) 0.0093(2) 0.0180(7) Uani 1 1 d . . . Co2 Co 1.0000 0.01715(5) 0.2500 0.0267(2) Uani 1 2 d S . . N2 N 0.96822(17) 0.4246(2) 0.1496(2) 0.0178(7) Uani 1 1 d . . . Cl1 Cl 0.88743(5) 0.57122(7) 0.20482(7) 0.0267(3) Uani 1 1 d . . . N5 N 0.92600(17) 0.1259(2) 0.1902(2) 0.0197(7) Uani 1 1 d . . . Cl2 Cl 0.97706(7) -0.02486(8) 0.09852(10) 0.0419(3) Uani 1 1 d . . . C13 C 1.0000 0.2747(3) 0.2500 0.0164(11) Uani 1 2 d S . . C25 C 0.9335(2) 0.2180(3) 0.2075(3) 0.0183(8) Uani 1 1 d . . . N1 N 0.95170(18) 0.6008(2) 0.1057(3) 0.0220(7) Uani 1 1 d . . . C11 C 0.9613(2) 0.2957(3) 0.0744(3) 0.0180(8) Uani 1 1 d . . . C10 C 0.9609(2) 0.2069(3) 0.0425(3) 0.0218(9) Uani 1 1 d . . . H10 H 0.9754 0.1567 0.0848 0.026 Uiso 1 1 calc R . . C12 C 0.9793(2) 0.3323(3) 0.1614(3) 0.0171(8) Uani 1 1 d . . . C8 C 0.9169(2) 0.2722(3) -0.1144(3) 0.0273(10) Uani 1 1 d . . . H8 H 0.9017 0.2632 -0.1781 0.033 Uiso 1 1 calc R . . N6 N 0.82153(18) 0.1786(2) 0.1324(2) 0.0224(7) Uani 1 1 d . . . C6 C 0.9447(2) 0.4482(3) 0.0593(3) 0.0185(8) Uani 1 1 d . . . C23 C 0.8435(2) 0.3423(3) 0.1678(3) 0.0246(9) Uani 1 1 d . . . H23 H 0.8736 0.3932 0.1922 0.030 Uiso 1 1 calc R . . C1 C 0.9307(2) 0.5449(3) 0.0288(3) 0.0217(9) Uani 1 1 d . . . C5 C 0.9426(2) 0.6914(3) 0.0892(3) 0.0268(9) Uani 1 1 d . . . H5 H 0.9575 0.7295 0.1424 0.032 Uiso 1 1 calc R . . C7 C 0.9170(2) 0.3579(3) -0.0857(3) 0.0229(9) Uani 1 1 d . . . H7 H 0.9030 0.4077 -0.1284 0.028 Uiso 1 1 calc R . . C2 C 0.8983(3) 0.5807(3) -0.0663(3) 0.0309(10) Uani 1 1 d . . . H2 H 0.8829 0.5419 -0.1192 0.037 Uiso 1 1 calc R . . C9 C 0.9392(2) 0.1948(3) -0.0502(3) 0.0270(9) Uani 1 1 d . . . H9 H 0.9390 0.1364 -0.0717 0.032 Uiso 1 1 calc R . . N4 N 1.1052(2) -0.0494(3) 0.3236(3) 0.0329(9) Uani 1 1 d . . . C19 C 0.8591(2) 0.1026(3) 0.1448(3) 0.0227(9) Uani 1 1 d . . . C4 C 0.9123(2) 0.7317(3) -0.0019(3) 0.0310(10) Uani 1 1 d . . . H4 H 0.9074 0.7952 -0.0099 0.037 Uiso 1 1 calc R . . C24 C 0.8694(2) 0.2538(3) 0.1729(3) 0.0210(8) Uani 1 1 d . . . O1 O 0.6224(2) 0.5891(3) 0.1650(4) 0.0641(12) Uani 1 1 d . . . H1 H 0.5858 0.5593 0.1387 0.096 Uiso 1 1 calc R . . C15 C 1.2330(3) -0.0266(3) 0.4388(4) 0.0399(12) Uani 1 1 d . . . H15 H 1.2720 0.0132 0.4776 0.048 Uiso 1 1 calc R . . C20 C 0.7523(2) 0.1904(3) 0.0944(3) 0.0310(10) Uani 1 1 d . . . H20 H 0.7217 0.1402 0.0703 0.037 Uiso 1 1 calc R . . C3 C 0.8895(3) 0.6754(3) -0.0805(3) 0.0343(11) Uani 1 1 d . . . H3 H 0.8682 0.7006 -0.1433 0.041 Uiso 1 1 calc R . . C22 C 0.7748(2) 0.3528(3) 0.1272(4) 0.0324(10) Uani 1 1 d . . . H22 H 0.7573 0.4111 0.1220 0.039 Uiso 1 1 calc R . . C18 C 1.1166(3) -0.1400(3) 0.3285(4) 0.0358(11) Uani 1 1 d . . . H18 H 1.0771 -0.1791 0.2920 0.043 Uiso 1 1 calc R . . C17 C 1.1841(3) -0.1783(3) 0.3850(4) 0.0438(13) Uani 1 1 d . . . H17 H 1.1896 -0.2415 0.3846 0.053 Uiso 1 1 calc R . . C16 C 1.2427(3) -0.1216(3) 0.4417(4) 0.0444(13) Uani 1 1 d . . . H16 H 1.2887 -0.1462 0.4819 0.053 Uiso 1 1 calc R . . C21 C 0.7297(3) 0.2747(3) 0.0925(4) 0.0362(11) Uani 1 1 d . . . H21 H 0.6834 0.2822 0.0680 0.043 Uiso 1 1 calc R . . C14 C 1.1634(2) 0.0061(3) 0.3764(3) 0.0275(10) Uani 1 1 d . . . C26 C 0.6721(3) 0.5343(5) 0.1715(5) 0.0627(17) Uani 1 1 d . . . H26A H 0.6474 0.5006 0.1088 0.075 Uiso 1 1 calc R . . H26B H 0.6937 0.4899 0.2258 0.075 Uiso 1 1 calc R . . C27 C 0.7280(4) 0.5912(5) 0.1905(7) 0.088(3) Uani 1 1 d . . . H27A H 0.7108 0.6173 0.1280 0.132 Uiso 1 1 calc R . . H27B H 0.7696 0.5543 0.2196 0.132 Uiso 1 1 calc R . . H27C H 0.7404 0.6398 0.2365 0.132 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 Co1 0.0230(4) 0.0151(4) 0.0193(4) 0.000 0.0145(4) 0.000 N3 0.0187(17) 0.0193(17) 0.0181(16) -0.0015(13) 0.0130(15) -0.0014(13) Co2 0.0294(5) 0.0134(4) 0.0254(4) 0.000 0.0133(4) 0.000 N2 0.0202(17) 0.0171(16) 0.0179(16) 0.0009(13) 0.0135(15) -0.0001(13) Cl1 0.0249(5) 0.0281(6) 0.0261(5) -0.0021(4) 0.0165(5) 0.0032(4) N5 0.0205(17) 0.0173(17) 0.0196(16) 0.0000(13) 0.0126(15) -0.0026(13) Cl2 0.0516(8) 0.0361(7) 0.0424(7) -0.0067(5) 0.0331(7) 0.0011(5) C13 0.021(3) 0.012(3) 0.020(3) 0.000 0.015(2) 0.000 C25 0.022(2) 0.0151(19) 0.0199(19) 0.0004(15) 0.0148(18) -0.0019(16) N1 0.0220(18) 0.0203(17) 0.0236(17) 0.0026(14) 0.0151(16) 0.0004(14) C11 0.0175(19) 0.019(2) 0.0190(19) 0.0001(15) 0.0128(17) 0.0004(15) C10 0.024(2) 0.021(2) 0.029(2) -0.0036(17) 0.0204(19) -0.0022(16) C12 0.0177(19) 0.0168(19) 0.0203(19) 0.0001(15) 0.0141(17) -0.0021(15) C8 0.031(2) 0.032(2) 0.023(2) -0.0046(18) 0.020(2) 0.0007(19) N6 0.0192(17) 0.0231(18) 0.0244(18) 0.0008(14) 0.0142(16) -0.0020(14) C6 0.019(2) 0.0160(19) 0.0202(19) -0.0005(16) 0.0130(18) -0.0004(15) C23 0.026(2) 0.022(2) 0.027(2) -0.0002(17) 0.019(2) 0.0010(17) C1 0.022(2) 0.022(2) 0.022(2) 0.0007(16) 0.0153(19) -0.0011(16) C5 0.031(2) 0.020(2) 0.028(2) 0.0007(17) 0.019(2) 0.0000(18) C7 0.025(2) 0.029(2) 0.020(2) 0.0028(17) 0.0167(19) 0.0031(17) C2 0.038(3) 0.027(2) 0.024(2) 0.0017(18) 0.019(2) -0.0004(19) C9 0.033(2) 0.026(2) 0.033(2) -0.0064(18) 0.026(2) 0.0004(18) N4 0.038(2) 0.025(2) 0.035(2) 0.0020(16) 0.0235(19) 0.0011(17) C19 0.021(2) 0.021(2) 0.021(2) 0.0007(16) 0.0125(18) -0.0025(17) C4 0.035(3) 0.020(2) 0.036(2) 0.0062(19) 0.023(2) 0.0036(19) C24 0.024(2) 0.021(2) 0.021(2) -0.0017(16) 0.0161(19) -0.0032(16) O1 0.052(3) 0.075(3) 0.066(3) -0.008(2) 0.040(2) -0.002(2) C15 0.041(3) 0.027(2) 0.043(3) 0.000(2) 0.024(3) 0.004(2) C20 0.021(2) 0.035(3) 0.032(2) 0.000(2) 0.015(2) -0.0051(19) C3 0.037(3) 0.028(2) 0.025(2) 0.0103(19) 0.015(2) 0.002(2) C22 0.033(2) 0.028(2) 0.041(3) -0.001(2) 0.026(2) 0.004(2) C18 0.040(3) 0.023(2) 0.037(3) -0.001(2) 0.023(2) 0.002(2) C17 0.051(3) 0.021(2) 0.041(3) 0.003(2) 0.023(3) 0.009(2) C16 0.041(3) 0.031(3) 0.046(3) 0.008(2) 0.023(3) 0.013(2) C21 0.026(2) 0.038(3) 0.045(3) 0.002(2) 0.023(2) 0.001(2) C14 0.027(2) 0.019(2) 0.035(2) -0.0023(18) 0.020(2) 0.0007(18) C26 0.055(4) 0.068(4) 0.057(4) 0.004(3) 0.034(3) 0.015(3) C27 0.048(4) 0.085(5) 0.127(7) -0.035(5) 0.057(5) -0.005(4) _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 N2 2.100(3) . ? Co1 N2 2.100(3) 2_755 ? Co1 N1 2.203(3) 2_755 ? Co1 N1 2.203(3) . ? Co1 Cl1 2.4161(11) 2_755 ? Co1 Cl1 2.4161(11) . ? N3 C6 1.377(5) . ? N3 C7 1.395(5) . ? N3 C11 1.405(5) . ? Co2 N5 2.103(3) 2_755 ? Co2 N5 2.103(3) . ? Co2 N4 2.229(4) 2_755 ? Co2 N4 2.229(4) . ? Co2 Cl2 2.4189(13) . ? Co2 Cl2 2.4189(13) 2_755 ? N2 C6 1.329(5) . ? N2 C12 1.357(5) . ? N5 C19 1.328(5) . ? N5 C25 1.359(5) . ? C13 C25 1.528(5) . ? C13 C25 1.528(5) 2_755 ? C13 C12 1.534(4) 2_755 ? C13 C12 1.534(4) . ? C25 C24 1.377(6) . ? N1 C5 1.335(5) . ? N1 C1 1.356(5) . ? C11 C12 1.390(5) . ? C11 C10 1.406(5) . ? C10 C9 1.356(6) . ? C10 H10 0.9300 . ? C8 C7 1.345(6) . ? C8 C9 1.422(6) . ? C8 H8 0.9300 . ? N6 C19 1.367(5) . ? N6 C20 1.385(5) . ? N6 C24 1.414(5) . ? C6 C1 1.463(5) . ? C23 C22 1.355(6) . ? C23 C24 1.415(6) . ? C23 H23 0.9300 . ? C1 C2 1.396(6) . ? C5 C4 1.377(6) . ? C5 H5 0.9300 . ? C7 H7 0.9300 . ? C2 C3 1.391(6) . ? C2 H2 0.9300 . ? C9 H9 0.9300 . ? N4 C18 1.338(6) . ? N4 C14 1.352(6) . ? C19 C14 1.465(6) 2_755 ? C4 C3 1.370(7) . ? C4 H4 0.9300 . ? O1 C26 1.413(7) . ? O1 H1 0.8200 . ? C15 C14 1.380(7) . ? C15 C16 1.397(7) . ? C15 H15 0.9300 . ? C20 C21 1.340(7) . ? C20 H20 0.9300 . ? C3 H3 0.9300 . ? C22 C21 1.418(7) . ? C22 H22 0.9300 . ? C18 C17 1.380(7) . ? C18 H18 0.9300 . ? C17 C16 1.367(8) . ? C17 H17 0.9300 . ? C16 H16 0.9300 . ? C21 H21 0.9300 . ? C14 C19 1.465(6) 2_755 ? C26 C27 1.454(10) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 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 N2 Co1 N2 82.45(17) . 2_755 ? N2 Co1 N1 157.66(13) . 2_755 ? N2 Co1 N1 75.28(12) 2_755 2_755 ? N2 Co1 N1 75.28(12) . . ? N2 Co1 N1 157.66(13) 2_755 . ? N1 Co1 N1 127.03(18) 2_755 . ? N2 Co1 Cl1 98.81(9) . 2_755 ? N2 Co1 Cl1 100.98(9) 2_755 2_755 ? N1 Co1 Cl1 84.01(9) 2_755 2_755 ? N1 Co1 Cl1 84.30(9) . 2_755 ? N2 Co1 Cl1 100.98(9) . . ? N2 Co1 Cl1 98.81(9) 2_755 . ? N1 Co1 Cl1 84.30(9) 2_755 . ? N1 Co1 Cl1 84.01(9) . . ? Cl1 Co1 Cl1 153.59(6) 2_755 . ? C6 N3 C7 132.4(3) . . ? C6 N3 C11 107.1(3) . . ? C7 N3 C11 120.5(3) . . ? N5 Co2 N5 82.60(17) 2_755 . ? N5 Co2 N4 156.57(13) 2_755 2_755 ? N5 Co2 N4 74.59(13) . 2_755 ? N5 Co2 N4 74.59(13) 2_755 . ? N5 Co2 N4 156.57(13) . . ? N4 Co2 N4 128.6(2) 2_755 . ? N5 Co2 Cl2 103.27(10) 2_755 . ? N5 Co2 Cl2 98.61(9) . . ? N4 Co2 Cl2 85.64(11) 2_755 . ? N4 Co2 Cl2 81.77(11) . . ? N5 Co2 Cl2 98.61(9) 2_755 2_755 ? N5 Co2 Cl2 103.27(10) . 2_755 ? N4 Co2 Cl2 81.77(11) 2_755 2_755 ? N4 Co2 Cl2 85.64(11) . 2_755 ? Cl2 Co2 Cl2 150.75(7) . 2_755 ? C6 N2 C12 108.8(3) . . ? C6 N2 Co1 116.1(3) . . ? C12 N2 Co1 133.6(3) . . ? C19 N5 C25 108.4(3) . . ? C19 N5 Co2 116.3(3) . . ? C25 N5 Co2 133.1(3) . . ? C25 C13 C25 114.7(4) . 2_755 ? C25 C13 C12 108.3(2) . 2_755 ? C25 C13 C12 105.90(19) 2_755 2_755 ? C25 C13 C12 105.90(19) . . ? C25 C13 C12 108.3(2) 2_755 . ? C12 C13 C12 113.9(4) 2_755 . ? N5 C25 C24 109.1(3) . . ? N5 C25 C13 125.7(3) . . ? C24 C25 C13 125.0(4) . . ? C5 N1 C1 118.5(4) . . ? C5 N1 Co1 125.1(3) . . ? C1 N1 Co1 116.4(3) . . ? C12 C11 C10 135.0(4) . . ? C12 C11 N3 105.6(3) . . ? C10 C11 N3 119.4(3) . . ? C9 C10 C11 119.8(4) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? N2 C12 C11 109.0(3) . . ? N2 C12 C13 126.3(3) . . ? C11 C12 C13 124.4(3) . . ? C7 C8 C9 122.0(4) . . ? C7 C8 H8 119.0 . . ? C9 C8 H8 119.0 . . ? C19 N6 C20 132.6(4) . . ? C19 N6 C24 106.6(3) . . ? C20 N6 C24 120.7(4) . . ? N2 C6 N3 109.5(3) . . ? N2 C6 C1 119.9(3) . . ? N3 C6 C1 130.6(4) . . ? C22 C23 C24 119.9(4) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? N1 C1 C2 121.0(4) . . ? N1 C1 C6 111.5(3) . . ? C2 C1 C6 127.5(4) . . ? N1 C5 C4 123.8(4) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C8 C7 N3 118.8(4) . . ? C8 C7 H7 120.6 . . ? N3 C7 H7 120.6 . . ? C3 C2 C1 118.8(4) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C10 C9 C8 119.6(4) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C18 N4 C14 117.2(4) . . ? C18 N4 Co2 125.6(3) . . ? C14 N4 Co2 116.8(3) . . ? N5 C19 N6 110.1(3) . . ? N5 C19 C14 120.8(4) . 2_755 ? N6 C19 C14 128.9(4) . 2_755 ? C3 C4 C5 118.1(4) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? C25 C24 N6 105.8(3) . . ? C25 C24 C23 135.8(4) . . ? N6 C24 C23 118.3(4) . . ? C26 O1 H1 109.5 . . ? C14 C15 C16 117.7(5) . . ? C14 C15 H15 121.2 . . ? C16 C15 H15 121.2 . . ? C21 C20 N6 119.6(4) . . ? C21 C20 H20 120.2 . . ? N6 C20 H20 120.2 . . ? C4 C3 C2 119.9(4) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C23 C22 C21 119.9(4) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? N4 C18 C17 123.3(5) . . ? N4 C18 H18 118.4 . . ? C17 C18 H18 118.4 . . ? C16 C17 C18 118.8(4) . . ? C16 C17 H17 120.6 . . ? C18 C17 H17 120.6 . . ? C17 C16 C15 119.6(5) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C20 C21 C22 121.4(4) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? N4 C14 C15 123.3(4) . . ? N4 C14 C19 110.0(4) . 2_755 ? C15 C14 C19 126.7(4) . 2_755 ? O1 C26 C27 110.5(6) . . ? O1 C26 H26A 109.5 . . ? C27 C26 H26A 109.5 . . ? O1 C26 H26B 109.5 . . ? C27 C26 H26B 109.5 . . ? H26A C26 H26B 108.1 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? 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 N2 Co1 N2 C6 -174.2(3) 2_755 . . . ? N1 Co1 N2 C6 -169.9(3) 2_755 . . . ? N1 Co1 N2 C6 7.5(3) . . . . ? Cl1 Co1 N2 C6 -74.2(3) 2_755 . . . ? Cl1 Co1 N2 C6 88.2(3) . . . . ? N2 Co1 N2 C12 -10.3(3) 2_755 . . . ? N1 Co1 N2 C12 -6.0(6) 2_755 . . . ? N1 Co1 N2 C12 171.4(4) . . . . ? Cl1 Co1 N2 C12 89.7(3) 2_755 . . . ? Cl1 Co1 N2 C12 -107.9(3) . . . . ? N5 Co2 N5 C19 -172.5(4) 2_755 . . . ? N4 Co2 N5 C19 2.1(3) 2_755 . . . ? N4 Co2 N5 C19 174.3(3) . . . . ? Cl2 Co2 N5 C19 85.1(3) . . . . ? Cl2 Co2 N5 C19 -75.4(3) 2_755 . . . ? N5 Co2 N5 C25 -11.5(3) 2_755 . . . ? N4 Co2 N5 C25 163.1(4) 2_755 . . . ? N4 Co2 N5 C25 -24.7(6) . . . . ? Cl2 Co2 N5 C25 -113.9(3) . . . . ? Cl2 Co2 N5 C25 85.6(4) 2_755 . . . ? C19 N5 C25 C24 0.6(4) . . . . ? Co2 N5 C25 C24 -161.5(3) . . . . ? C19 N5 C25 C13 -174.5(3) . . . . ? Co2 N5 C25 C13 23.4(6) . . . . ? C25 C13 C25 N5 -11.2(3) 2_755 . . . ? C12 C13 C25 N5 -129.2(4) 2_755 . . . ? C12 C13 C25 N5 108.3(4) . . . . ? C25 C13 C25 C24 174.5(4) 2_755 . . . ? C12 C13 C25 C24 56.5(4) 2_755 . . . ? C12 C13 C25 C24 -66.0(4) . . . . ? N2 Co1 N1 C5 176.6(4) . . . . ? N2 Co1 N1 C5 172.2(3) 2_755 . . . ? N1 Co1 N1 C5 -4.6(3) 2_755 . . . ? Cl1 Co1 N1 C5 -82.7(3) 2_755 . . . ? Cl1 Co1 N1 C5 73.6(3) . . . . ? N2 Co1 N1 C1 -4.1(3) . . . . ? N2 Co1 N1 C1 -8.6(5) 2_755 . . . ? N1 Co1 N1 C1 174.6(3) 2_755 . . . ? Cl1 Co1 N1 C1 96.6(3) 2_755 . . . ? Cl1 Co1 N1 C1 -107.2(3) . . . . ? C6 N3 C11 C12 0.6(4) . . . . ? C7 N3 C11 C12 179.5(3) . . . . ? C6 N3 C11 C10 -179.8(3) . . . . ? C7 N3 C11 C10 -0.9(5) . . . . ? C12 C11 C10 C9 179.8(4) . . . . ? N3 C11 C10 C9 0.4(6) . . . . ? C6 N2 C12 C11 -0.7(4) . . . . ? Co1 N2 C12 C11 -165.5(3) . . . . ? C6 N2 C12 C13 -174.2(3) . . . . ? Co1 N2 C12 C13 21.0(6) . . . . ? C10 C11 C12 N2 -179.4(4) . . . . ? N3 C11 C12 N2 0.1(4) . . . . ? C10 C11 C12 C13 -5.8(7) . . . . ? N3 C11 C12 C13 173.7(3) . . . . ? C25 C13 C12 N2 108.9(4) . . . . ? C25 C13 C12 N2 -127.5(4) 2_755 . . . ? C12 C13 C12 N2 -10.0(3) 2_755 . . . ? C25 C13 C12 C11 -63.6(4) . . . . ? C25 C13 C12 C11 59.9(4) 2_755 . . . ? C12 C13 C12 C11 177.5(4) 2_755 . . . ? C12 N2 C6 N3 1.1(4) . . . . ? Co1 N2 C6 N3 168.9(2) . . . . ? C12 N2 C6 C1 -178.0(3) . . . . ? Co1 N2 C6 C1 -10.3(5) . . . . ? C7 N3 C6 N2 -179.8(4) . . . . ? C11 N3 C6 N2 -1.0(4) . . . . ? C7 N3 C6 C1 -0.8(7) . . . . ? C11 N3 C6 C1 177.9(4) . . . . ? C5 N1 C1 C2 -1.9(6) . . . . ? Co1 N1 C1 C2 178.8(3) . . . . ? C5 N1 C1 C6 179.8(4) . . . . ? Co1 N1 C1 C6 0.5(4) . . . . ? N2 C6 C1 N1 6.3(5) . . . . ? N3 C6 C1 N1 -172.5(4) . . . . ? N2 C6 C1 C2 -171.9(4) . . . . ? N3 C6 C1 C2 9.2(7) . . . . ? C1 N1 C5 C4 0.7(7) . . . . ? Co1 N1 C5 C4 179.9(3) . . . . ? C9 C8 C7 N3 -1.1(6) . . . . ? C6 N3 C7 C8 179.9(4) . . . . ? C11 N3 C7 C8 1.2(6) . . . . ? N1 C1 C2 C3 1.7(7) . . . . ? C6 C1 C2 C3 179.8(4) . . . . ? C11 C10 C9 C8 -0.2(6) . . . . ? C7 C8 C9 C10 0.6(7) . . . . ? N5 Co2 N4 C18 178.8(4) 2_755 . . . ? N5 Co2 N4 C18 -167.6(3) . . . . ? N4 Co2 N4 C18 2.8(4) 2_755 . . . ? Cl2 Co2 N4 C18 -74.9(4) . . . . ? Cl2 Co2 N4 C18 78.6(4) 2_755 . . . ? N5 Co2 N4 C14 6.0(3) 2_755 . . . ? N5 Co2 N4 C14 19.6(6) . . . . ? N4 Co2 N4 C14 -170.0(4) 2_755 . . . ? Cl2 Co2 N4 C14 112.3(3) . . . . ? Cl2 Co2 N4 C14 -94.1(3) 2_755 . . . ? C25 N5 C19 N6 -0.6(5) . . . . ? Co2 N5 C19 N6 164.9(2) . . . . ? C25 N5 C19 C14 -175.3(4) . . . 2_755 ? Co2 N5 C19 C14 -9.8(5) . . . 2_755 ? C20 N6 C19 N5 -176.6(4) . . . . ? C24 N6 C19 N5 0.4(4) . . . . ? C20 N6 C19 C14 -2.4(8) . . . 2_755 ? C24 N6 C19 C14 174.5(4) . . . 2_755 ? N1 C5 C4 C3 0.7(7) . . . . ? N5 C25 C24 N6 -0.4(4) . . . . ? C13 C25 C24 N6 174.8(3) . . . . ? N5 C25 C24 C23 -178.8(4) . . . . ? C13 C25 C24 C23 -3.7(7) . . . . ? C19 N6 C24 C25 0.0(4) . . . . ? C20 N6 C24 C25 177.4(4) . . . . ? C19 N6 C24 C23 178.7(4) . . . . ? C20 N6 C24 C23 -3.9(6) . . . . ? C22 C23 C24 C25 179.9(5) . . . . ? C22 C23 C24 N6 1.7(6) . . . . ? C19 N6 C20 C21 179.1(4) . . . . ? C24 N6 C20 C21 2.5(6) . . . . ? C5 C4 C3 C2 -0.9(7) . . . . ? C1 C2 C3 C4 -0.3(7) . . . . ? C24 C23 C22 C21 1.8(7) . . . . ? C14 N4 C18 C17 0.7(7) . . . . ? Co2 N4 C18 C17 -172.1(4) . . . . ? N4 C18 C17 C16 2.2(8) . . . . ? C18 C17 C16 C15 -1.9(8) . . . . ? C14 C15 C16 C17 -1.1(8) . . . . ? N6 C20 C21 C22 1.1(7) . . . . ? C23 C22 C21 C20 -3.3(7) . . . . ? C18 N4 C14 C15 -4.0(7) . . . . ? Co2 N4 C14 C15 169.4(4) . . . . ? C18 N4 C14 C19 174.8(4) . . . 2_755 ? Co2 N4 C14 C19 -11.8(5) . . . 2_755 ? C16 C15 C14 N4 4.2(8) . . . . ? C16 C15 C14 C19 -174.3(5) . . . 2_755 ? 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 O1 H1 Cl2 0.82 2.61 3.404(5) 165.1 3_455 C10 H10 Cl2 0.93 2.65 3.459(4) 146.1 . C23 H23 Cl1 0.93 2.60 3.427(4) 148.4 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.665 _refine_diff_density_min -0.846 _refine_diff_density_rms 0.095 data_1(ccdc888199) _database_code_depnum_ccdc_archive 'CCDC 888199' #TrackingRef '17091_web_deposit_cif_file_0_YanmeiChen_1358858065.CCDC 888199.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C49 H32 Cl2 Cu2 N12, Cl4 Cu2, 2(C2 H6 O)' _chemical_formula_sum 'C53 H44 Cl6 Cu4 N12 O2' _chemical_formula_weight 1347.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/c' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 12.4628(18) _cell_length_b 10.8337(15) _cell_length_c 20.597(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.875(3) _cell_angle_gamma 90.00 _cell_volume 2674.9(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4291 _cell_measurement_theta_min 2.531 _cell_measurement_theta_max 23.275 _exptl_crystal_description platy _exptl_crystal_colour dark-green _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.673 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 1.923 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6660 _exptl_absorpt_correction_T_max 0.7114 _exptl_absorpt_process_details 'SADABS (Bruker, 2005)' _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 'Bruker APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18969 _diffrn_reflns_av_R_equivalents 0.0704 _diffrn_reflns_av_sigmaI/netI 0.0852 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.68 _reflns_number_total 5028 _reflns_number_gt 3927 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX-II (Bruker, 2005)' _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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. The disorder of ethanol molecule was solved. DFIX restraints were used for reas SADI restraint was used for reasonable 1,3 distances between O1 C27 and O1B C27B. OMIT restrains were used to omit the weak reflections. Thermal motion of C26, C27, C26B, C27B, O1 and O1B are restrained by commond 'SIMU'. The R factors for this structure are relatively high, we have tried to use comments OMIT, SIMU and DFIX to reduce the R value, but it's hard to do that. The ring atoms in the organic ligand haven't modeled as disorderde. ; _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^)+(0.0000P)^2^+36.5375P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5028 _refine_ls_number_parameters 386 _refine_ls_number_restraints 95 _refine_ls_R_factor_all 0.1474 _refine_ls_R_factor_gt 0.1288 _refine_ls_wR_factor_ref 0.3017 _refine_ls_wR_factor_gt 0.2922 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.120 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.27914(11) 0.16641(13) 0.09278(6) 0.0545(4) Uani 1 1 d . . . Cl1 Cl 0.3426(3) 0.3204(3) 0.01974(15) 0.0834(11) Uani 1 1 d . . . N2 N 0.3099(7) 0.2542(8) 0.1785(4) 0.048(2) Uani 1 1 d . . . N1 N 0.1334(9) 0.2593(11) 0.0780(5) 0.071(3) Uani 1 1 d . . . C1 C 0.1315(10) 0.3384(11) 0.1291(6) 0.065(3) Uani 1 1 d . . . C2 C 0.0405(10) 0.4158(16) 0.1214(7) 0.087(5) Uani 1 1 d . . . H2 H 0.0393 0.4707 0.1558 0.104 Uiso 1 1 calc R . . C3 C -0.0460(15) 0.4142(18) 0.0656(10) 0.104(5) Uani 1 1 d . . . H3 H -0.1059 0.4675 0.0621 0.125 Uiso 1 1 calc R . . C4 C -0.0465(15) 0.338(2) 0.0160(9) 0.117(7) Uani 1 1 d . . . H4 H -0.1066 0.3346 -0.0225 0.140 Uiso 1 1 calc R . . C5 C 0.0456(14) 0.2614(16) 0.0230(8) 0.103(6) Uani 1 1 d . . . H5 H 0.0465 0.2087 -0.0125 0.124 Uiso 1 1 calc R . . N5 N 0.4179(8) 0.0773(8) 0.1344(4) 0.050(2) Uani 1 1 d . . . C6 C 0.2315(9) 0.3291(10) 0.1851(5) 0.054(3) Uani 1 1 d . . . N3 N 0.2616(8) 0.3829(8) 0.2473(5) 0.055(2) Uani 1 1 d . . . C7 C 0.2090(13) 0.4666(13) 0.2794(8) 0.085(4) Uani 1 1 d . . . H7 H 0.1383 0.4963 0.2575 0.102 Uiso 1 1 calc R . . C8 C 0.2593(13) 0.5037(13) 0.3409(8) 0.085(5) Uani 1 1 d . . . H8 H 0.2237 0.5597 0.3623 0.102 Uiso 1 1 calc R . . C9 C 0.3664(15) 0.4600(13) 0.3751(8) 0.091(5) Uani 1 1 d . . . H9 H 0.4008 0.4891 0.4183 0.109 Uiso 1 1 calc R . . C10 C 0.4211(11) 0.3755(12) 0.3459(6) 0.068(3) Uani 1 1 d . . . H10 H 0.4906 0.3443 0.3690 0.081 Uiso 1 1 calc R . . C11 C 0.3682(9) 0.3388(9) 0.2807(6) 0.052(2) Uani 1 1 d . . . C12 C 0.3972(8) 0.2559(8) 0.2355(5) 0.040(2) Uani 1 1 d . . . C13 C 0.5000 0.1743(11) 0.2500 0.039(3) Uani 1 2 d S . . N4 N 0.2655(8) 0.0275(10) 0.0225(5) 0.070(3) Uani 1 1 d . . . C14 C 0.3604(11) -0.0428(10) 0.0331(6) 0.060(3) Uani 1 1 d . . . C15 C 0.3680(15) -0.1352(13) -0.0118(7) 0.089(5) Uani 1 1 d . . . H15 H 0.4331 -0.1812 -0.0052 0.107 Uiso 1 1 calc R . . C16 C 0.2793(19) -0.1580(19) -0.0656(9) 0.121(7) Uani 1 1 d . . . H16 H 0.2832 -0.2195 -0.0963 0.145 Uiso 1 1 calc R . . C17 C 0.1848(18) -0.090(2) -0.0742(10) 0.132(8) Uani 1 1 d . . . H17 H 0.1227 -0.1087 -0.1097 0.158 Uiso 1 1 calc R . . C18 C 0.1798(12) 0.0038(19) -0.0314(9) 0.113(7) Uani 1 1 d . . . H18 H 0.1160 0.0524 -0.0397 0.135 Uiso 1 1 calc R . . C19 C 0.4441(10) -0.0082(10) 0.0950(5) 0.055(3) Uani 1 1 d . . . N6 N 0.5489(9) -0.0515(8) 0.1256(4) 0.060(3) Uani 1 1 d . . . C20 C 0.6127(13) -0.1379(12) 0.1044(6) 0.077(4) Uani 1 1 d . . . H20 H 0.5846 -0.1807 0.0642 0.093 Uiso 1 1 calc R . . C21 C 0.7144(18) -0.1586(17) 0.1425(8) 0.130(9) Uani 1 1 d . . . H21 H 0.7596 -0.2145 0.1280 0.156 Uiso 1 1 calc R . . C22 C 0.7566(18) -0.0976(19) 0.2050(8) 0.139(9) Uani 1 1 d . . . H22 H 0.8287 -0.1133 0.2315 0.167 Uiso 1 1 calc R . . C23 C 0.6908(16) -0.0165(16) 0.2257(6) 0.113(7) Uani 1 1 d . . . H23 H 0.7178 0.0234 0.2669 0.136 Uiso 1 1 calc R . . C24 C 0.5825(11) 0.0086(10) 0.1859(5) 0.060(3) Uani 1 1 d . . . C25 C 0.5017(9) 0.0917(8) 0.1909(4) 0.045(2) Uani 1 1 d . . . O1 O 0.324(4) 0.603(3) 0.067(2) 0.220(15) Uani 0.59(3) 1 d PDU A 1 H1 H 0.3591 0.5481 0.0546 0.330 Uiso 0.59(3) 1 calc PR A 1 C26 C 0.368(4) 0.624(4) 0.134(2) 0.182(15) Uani 0.59(3) 1 d PDU A 1 H26C H 0.4469 0.6400 0.1399 0.218 Uiso 0.59(3) 1 calc PR A 1 H26D H 0.3638 0.5459 0.1562 0.218 Uiso 0.59(3) 1 calc PR A 1 C27 C 0.327(4) 0.721(3) 0.173(2) 0.188(15) Uani 0.59(3) 1 d PDU A 1 H27D H 0.3897 0.7602 0.2035 0.283 Uiso 0.59(3) 1 calc PR A 1 H27E H 0.2808 0.6835 0.1975 0.283 Uiso 0.59(3) 1 calc PR A 1 H27F H 0.2848 0.7812 0.1421 0.283 Uiso 0.59(3) 1 calc PR A 1 O1B O 0.283(5) 0.543(3) 0.099(3) 0.202(15) Uani 0.41(3) 1 d PDU A 2 H1B H 0.3254 0.5375 0.0756 0.303 Uiso 0.41(3) 1 calc PR A 2 C26B C 0.299(6) 0.652(4) 0.132(4) 0.203(17) Uani 0.41(3) 1 d PDU A 2 H26A H 0.2329 0.6664 0.1478 0.243 Uiso 0.41(3) 1 calc PR A 2 H26B H 0.2977 0.7148 0.0983 0.243 Uiso 0.41(3) 1 calc PR A 2 C27B C 0.397(5) 0.680(5) 0.191(3) 0.179(16) Uani 0.41(3) 1 d PDU A 2 H27A H 0.4620 0.6920 0.1747 0.269 Uiso 0.41(3) 1 calc PR A 2 H27B H 0.4097 0.6128 0.2220 0.269 Uiso 0.41(3) 1 calc PR A 2 H27C H 0.3830 0.7541 0.2127 0.269 Uiso 0.41(3) 1 calc PR A 2 Cu2 Cu 0.0490(3) 1.0839(4) 0.19544(17) 0.0812(10) Uani 0.50 1 d P . . Cu3 Cu 0.0507(3) 0.8021(4) 0.1691(2) 0.0988(13) Uani 0.50 1 d P . . Cl2 Cl 0.1014(5) 0.9506(6) 0.1208(3) 0.148(2) Uani 1 1 d . . . Cl3 Cl 0.0000 1.2117(6) 0.2500 0.1097(19) Uani 1 2 d S . . Cl4 Cl 0.0000 0.6883(7) 0.2500 0.227(7) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0570(8) 0.0620(8) 0.0479(7) -0.0122(6) 0.0204(6) -0.0048(7) Cl1 0.124(3) 0.082(2) 0.0515(15) -0.0090(16) 0.0362(17) -0.026(2) N2 0.054(5) 0.050(5) 0.045(4) -0.005(4) 0.025(4) 0.002(4) N1 0.066(7) 0.088(8) 0.054(5) 0.005(5) 0.009(5) 0.003(6) C1 0.065(7) 0.061(7) 0.077(8) 0.016(6) 0.033(6) 0.016(6) C2 0.046(7) 0.132(13) 0.082(9) 0.028(9) 0.018(7) 0.032(8) C3 0.088(12) 0.117(14) 0.120(14) 0.015(12) 0.050(11) 0.031(10) C4 0.085(11) 0.165(19) 0.083(11) 0.019(12) -0.005(9) 0.039(13) C5 0.104(12) 0.110(13) 0.069(9) 0.006(9) -0.022(8) 0.010(10) N5 0.065(6) 0.045(5) 0.053(5) -0.003(4) 0.035(4) 0.005(4) C6 0.059(6) 0.055(6) 0.054(6) 0.004(5) 0.025(5) -0.001(5) N3 0.057(6) 0.048(5) 0.068(6) -0.014(4) 0.032(5) -0.003(4) C7 0.080(9) 0.082(10) 0.108(11) -0.029(9) 0.052(8) 0.011(8) C8 0.080(10) 0.077(9) 0.114(12) -0.053(9) 0.052(9) -0.011(8) C9 0.109(13) 0.078(9) 0.101(11) -0.050(8) 0.054(10) -0.011(9) C10 0.074(8) 0.072(8) 0.068(7) -0.021(6) 0.038(6) -0.012(7) C11 0.058(6) 0.040(5) 0.070(7) -0.012(5) 0.037(5) -0.001(5) C12 0.045(5) 0.040(5) 0.042(5) 0.001(4) 0.024(4) -0.001(4) C13 0.052(8) 0.031(6) 0.044(7) 0.000 0.028(6) 0.000 N4 0.054(6) 0.091(8) 0.070(6) -0.037(6) 0.027(5) -0.023(6) C14 0.082(8) 0.053(6) 0.057(6) -0.018(5) 0.040(6) -0.031(6) C15 0.123(13) 0.068(9) 0.090(10) -0.041(8) 0.052(9) -0.025(8) C16 0.139(17) 0.129(16) 0.113(13) -0.081(12) 0.067(13) -0.061(14) C17 0.103(14) 0.18(2) 0.119(14) -0.095(15) 0.043(12) -0.068(14) C18 0.055(8) 0.161(16) 0.115(12) -0.080(12) 0.012(8) -0.024(10) C19 0.081(8) 0.051(6) 0.043(5) -0.015(5) 0.036(5) -0.018(6) N6 0.099(8) 0.047(5) 0.042(5) 0.008(4) 0.033(5) 0.027(5) C20 0.111(11) 0.071(8) 0.053(6) -0.006(6) 0.029(7) 0.045(8) C21 0.19(2) 0.127(14) 0.067(9) 0.003(9) 0.029(11) 0.119(15) C22 0.163(18) 0.168(18) 0.072(10) -0.009(11) 0.010(10) 0.125(16) C23 0.154(15) 0.129(13) 0.048(7) -0.001(8) 0.014(8) 0.107(13) C24 0.090(9) 0.055(6) 0.042(5) 0.011(5) 0.028(5) 0.037(6) C25 0.070(7) 0.038(5) 0.034(5) 0.008(4) 0.026(5) 0.014(5) O1 0.28(3) 0.12(2) 0.30(4) 0.05(2) 0.15(3) 0.09(2) C26 0.24(3) 0.10(2) 0.27(4) 0.00(2) 0.18(3) 0.07(2) C27 0.26(3) 0.07(2) 0.29(4) 0.01(2) 0.17(3) 0.05(2) O1B 0.27(3) 0.08(2) 0.32(4) 0.02(2) 0.19(3) 0.02(2) C26B 0.27(4) 0.11(3) 0.28(4) 0.01(3) 0.16(3) 0.05(3) C27B 0.24(4) 0.08(3) 0.28(4) 0.02(3) 0.19(3) 0.02(3) Cu2 0.067(2) 0.105(3) 0.0656(19) -0.0013(19) 0.0080(15) -0.0047(19) Cu3 0.080(2) 0.101(3) 0.108(3) -0.006(2) 0.013(2) -0.003(2) Cl2 0.122(4) 0.194(6) 0.097(3) 0.033(4) -0.022(3) -0.046(4) Cl3 0.110(5) 0.103(4) 0.121(5) 0.000 0.040(4) 0.000 Cl4 0.100(5) 0.075(4) 0.55(2) 0.000 0.162(9) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.949(8) . ? Cu1 N5 1.962(9) . ? Cu1 N1 2.025(11) . ? Cu1 N4 2.062(9) . ? Cu1 Cl1 2.515(3) . ? N2 C6 1.306(13) . ? N2 C12 1.366(12) . ? N1 C5 1.344(16) . ? N1 C1 1.362(16) . ? C1 C2 1.384(17) . ? C1 C6 1.452(16) . ? C2 C3 1.34(2) . ? C2 H2 0.9300 . ? C3 C4 1.31(2) . ? C3 H3 0.9300 . ? C4 C5 1.39(2) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? N5 C19 1.329(12) . ? N5 C25 1.343(13) . ? C6 N3 1.363(13) . ? N3 C7 1.389(14) . ? N3 C11 1.402(14) . ? C7 C8 1.31(2) . ? C7 H7 0.9300 . ? C8 C9 1.41(2) . ? C8 H8 0.9300 . ? C9 C10 1.375(17) . ? C9 H9 0.9300 . ? C10 C11 1.383(16) . ? C10 H10 0.9300 . ? C11 C12 1.409(13) . ? C12 C13 1.518(12) . ? C13 C25 1.516(11) 2_655 ? C13 C25 1.516(11) . ? C13 C12 1.518(12) 2_655 ? N4 C18 1.338(16) . ? N4 C14 1.374(16) . ? C14 C15 1.383(15) . ? C14 C19 1.459(16) . ? C15 C16 1.36(2) . ? C15 H15 0.9300 . ? C16 C17 1.36(3) . ? C16 H16 0.9300 . ? C17 C18 1.36(2) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 N6 1.369(15) . ? N6 C24 1.364(14) . ? N6 C20 1.374(14) . ? C20 C21 1.31(2) . ? C20 H20 0.9300 . ? C21 C22 1.41(2) . ? C21 H21 0.9300 . ? C22 C23 1.347(18) . ? C22 H22 0.9300 . ? C23 C24 1.401(19) . ? C23 H23 0.9300 . ? C24 C25 1.375(14) . ? O1 C26 1.350(10) . ? O1 H1 0.8200 . ? C26 C27 1.497(10) . ? C26 H26C 0.9700 . ? C26 H26D 0.9700 . ? C27 H27D 0.9600 . ? C27 H27E 0.9600 . ? C27 H27F 0.9600 . ? O1B C26B 1.349(10) . ? O1B H1B 0.8200 . ? C26B C27B 1.498(10) . ? C26B H26A 0.9700 . ? C26B H26B 0.9700 . ? C27B H27A 0.9600 . ? C27B H27B 0.9600 . ? C27B H27C 0.9600 . ? Cu2 Cl3 1.983(6) . ? Cu2 Cl2 2.329(8) . ? Cu2 Cu2 2.837(7) 2 ? Cu3 Cl2 2.079(7) . ? Cu3 Cl4 2.296(6) . ? Cl3 Cu2 1.983(6) 2 ? Cl4 Cu3 2.296(6) 2 ? 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 N2 Cu1 N5 85.0(3) . . ? N2 Cu1 N1 80.8(4) . . ? N5 Cu1 N1 163.2(4) . . ? N2 Cu1 N4 161.7(4) . . ? N5 Cu1 N4 80.9(4) . . ? N1 Cu1 N4 111.0(4) . . ? N2 Cu1 Cl1 101.7(3) . . ? N5 Cu1 Cl1 101.8(3) . . ? N1 Cu1 Cl1 89.8(3) . . ? N4 Cu1 Cl1 92.5(3) . . ? C6 N2 C12 110.2(8) . . ? C6 N2 Cu1 115.5(7) . . ? C12 N2 Cu1 134.3(7) . . ? C5 N1 C1 117.3(13) . . ? C5 N1 Cu1 128.7(11) . . ? C1 N1 Cu1 113.7(8) . . ? N1 C1 C2 118.6(13) . . ? N1 C1 C6 112.2(10) . . ? C2 C1 C6 129.2(13) . . ? C3 C2 C1 122.1(16) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C4 C3 C2 120.3(16) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 117.8(16) . . ? C3 C4 H4 121.1 . . ? C5 C4 H4 121.1 . . ? N1 C5 C4 123.9(17) . . ? N1 C5 H5 118.1 . . ? C4 C5 H5 118.1 . . ? C19 N5 C25 110.3(9) . . ? C19 N5 Cu1 114.2(8) . . ? C25 N5 Cu1 134.9(7) . . ? N2 C6 N3 110.0(9) . . ? N2 C6 C1 117.6(10) . . ? N3 C6 C1 132.3(10) . . ? C6 N3 C7 133.0(11) . . ? C6 N3 C11 107.2(8) . . ? C7 N3 C11 119.8(10) . . ? C8 C7 N3 119.8(14) . . ? C8 C7 H7 120.1 . . ? N3 C7 H7 120.1 . . ? C7 C8 C9 121.1(12) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C10 C9 C8 121.4(14) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C11 117.0(13) . . ? C9 C10 H10 121.5 . . ? C11 C10 H10 121.5 . . ? C10 C11 N3 121.0(9) . . ? C10 C11 C12 133.1(11) . . ? N3 C11 C12 105.9(9) . . ? N2 C12 C11 106.7(9) . . ? N2 C12 C13 126.3(8) . . ? C11 C12 C13 126.7(8) . . ? C25 C13 C25 107.6(10) 2_655 . ? C25 C13 C12 112.5(5) 2_655 2_655 ? C25 C13 C12 107.8(5) . 2_655 ? C25 C13 C12 107.8(5) 2_655 . ? C25 C13 C12 112.5(5) . . ? C12 C13 C12 108.8(10) 2_655 . ? C18 N4 C14 118.8(11) . . ? C18 N4 Cu1 128.1(11) . . ? C14 N4 Cu1 113.1(7) . . ? N4 C14 C15 120.6(12) . . ? N4 C14 C19 112.0(9) . . ? C15 C14 C19 127.4(14) . . ? C16 C15 C14 119.2(17) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C17 C16 C15 119.5(15) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 120.8(17) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? N4 C18 C17 121.0(18) . . ? N4 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? N5 C19 N6 108.7(9) . . ? N5 C19 C14 118.5(11) . . ? N6 C19 C14 132.7(10) . . ? C24 N6 C19 105.8(8) . . ? C24 N6 C20 123.7(11) . . ? C19 N6 C20 130.5(10) . . ? C21 C20 N6 118.3(12) . . ? C21 C20 H20 120.9 . . ? N6 C20 H20 120.8 . . ? C20 C21 C22 121.4(13) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C23 C22 C21 119.0(16) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? C22 C23 C24 121.0(14) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? N6 C24 C25 109.4(10) . . ? N6 C24 C23 116.5(10) . . ? C25 C24 C23 133.8(11) . . ? N5 C25 C24 105.8(9) . . ? N5 C25 C13 125.9(8) . . ? C24 C25 C13 128.1(9) . . ? C26 O1 H1 109.5 . . ? O1 C26 C27 124(3) . . ? O1 C26 H26C 106.4 . . ? C27 C26 H26C 106.4 . . ? O1 C26 H26D 106.4 . . ? C27 C26 H26D 106.4 . . ? H26C C26 H26D 106.4 . . ? C26 C27 H27D 109.5 . . ? C26 C27 H27E 109.5 . . ? H27D C27 H27E 109.5 . . ? C26 C27 H27F 109.5 . . ? H27D C27 H27F 109.5 . . ? H27E C27 H27F 109.5 . . ? C26B O1B H1B 109.5 . . ? O1B C26B C27B 124(3) . . ? O1B C26B H26A 106.4 . . ? C27B C26B H26A 106.4 . . ? O1B C26B H26B 106.4 . . ? C27B C26B H26B 106.4 . . ? H26A C26B H26B 106.4 . . ? C26B C27B H27A 109.5 . . ? C26B C27B H27B 109.5 . . ? H27A C27B H27B 109.5 . . ? C26B C27B H27C 109.5 . . ? H27A C27B H27C 109.5 . . ? H27B C27B H27C 109.5 . . ? Cl3 Cu2 Cl2 173.2(3) . . ? Cl3 Cu2 Cu2 44.32(18) . 2 ? Cl2 Cu2 Cu2 141.48(17) . 2 ? Cl2 Cu3 Cl4 160.6(3) . . ? Cu3 Cl2 Cu2 89.2(3) . . ? Cu2 Cl3 Cu2 91.4(4) . 2 ? Cu3 Cl4 Cu3 115.0(4) 2 . ? 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 N5 Cu1 N2 C6 -173.5(8) . . . . ? N1 Cu1 N2 C6 -2.4(8) . . . . ? N4 Cu1 N2 C6 -134.3(12) . . . . ? Cl1 Cu1 N2 C6 85.4(7) . . . . ? N5 Cu1 N2 C12 6.3(9) . . . . ? N1 Cu1 N2 C12 177.4(10) . . . . ? N4 Cu1 N2 C12 45.6(17) . . . . ? Cl1 Cu1 N2 C12 -94.7(9) . . . . ? N2 Cu1 N1 C5 177.3(14) . . . . ? N5 Cu1 N1 C5 -150.5(14) . . . . ? N4 Cu1 N1 C5 -17.2(15) . . . . ? Cl1 Cu1 N1 C5 75.4(13) . . . . ? N2 Cu1 N1 C1 4.3(8) . . . . ? N5 Cu1 N1 C1 37(2) . . . . ? N4 Cu1 N1 C1 169.8(8) . . . . ? Cl1 Cu1 N1 C1 -97.6(8) . . . . ? C5 N1 C1 C2 -0.3(19) . . . . ? Cu1 N1 C1 C2 173.6(10) . . . . ? C5 N1 C1 C6 -179.0(12) . . . . ? Cu1 N1 C1 C6 -5.2(13) . . . . ? N1 C1 C2 C3 1(2) . . . . ? C6 C1 C2 C3 179.3(14) . . . . ? C1 C2 C3 C4 0(3) . . . . ? C2 C3 C4 C5 -1(3) . . . . ? C1 N1 C5 C4 -1(3) . . . . ? Cu1 N1 C5 C4 -173.8(15) . . . . ? C3 C4 C5 N1 2(3) . . . . ? N2 Cu1 N5 C19 179.2(8) . . . . ? N1 Cu1 N5 C19 147.3(13) . . . . ? N4 Cu1 N5 C19 10.8(7) . . . . ? Cl1 Cu1 N5 C19 -79.9(7) . . . . ? N2 Cu1 N5 C25 -10.9(10) . . . . ? N1 Cu1 N5 C25 -43(2) . . . . ? N4 Cu1 N5 C25 -179.4(10) . . . . ? Cl1 Cu1 N5 C25 90.0(9) . . . . ? C12 N2 C6 N3 -1.0(12) . . . . ? Cu1 N2 C6 N3 178.9(7) . . . . ? C12 N2 C6 C1 -179.6(9) . . . . ? Cu1 N2 C6 C1 0.3(13) . . . . ? N1 C1 C6 N2 3.4(15) . . . . ? C2 C1 C6 N2 -175.2(13) . . . . ? N1 C1 C6 N3 -174.9(11) . . . . ? C2 C1 C6 N3 7(2) . . . . ? N2 C6 N3 C7 -179.1(12) . . . . ? C1 C6 N3 C7 -1(2) . . . . ? N2 C6 N3 C11 1.2(12) . . . . ? C1 C6 N3 C11 179.6(12) . . . . ? C6 N3 C7 C8 -179.8(13) . . . . ? C11 N3 C7 C8 0(2) . . . . ? N3 C7 C8 C9 0(2) . . . . ? C7 C8 C9 C10 -1(2) . . . . ? C8 C9 C10 C11 2(2) . . . . ? C9 C10 C11 N3 -2.4(17) . . . . ? C9 C10 C11 C12 -179.8(12) . . . . ? C6 N3 C11 C10 -178.9(10) . . . . ? C7 N3 C11 C10 1.3(16) . . . . ? C6 N3 C11 C12 -1.0(11) . . . . ? C7 N3 C11 C12 179.3(10) . . . . ? C6 N2 C12 C11 0.4(11) . . . . ? Cu1 N2 C12 C11 -179.5(7) . . . . ? C6 N2 C12 C13 174.7(9) . . . . ? Cu1 N2 C12 C13 -5.1(15) . . . . ? C10 C11 C12 N2 178.0(12) . . . . ? N3 C11 C12 N2 0.4(11) . . . . ? C10 C11 C12 C13 3.7(19) . . . . ? N3 C11 C12 C13 -173.9(9) . . . . ? N2 C12 C13 C25 -114.6(9) . . . 2_655 ? C11 C12 C13 C25 58.6(12) . . . 2_655 ? N2 C12 C13 C25 3.9(13) . . . . ? C11 C12 C13 C25 177.1(9) . . . . ? N2 C12 C13 C12 123.2(10) . . . 2_655 ? C11 C12 C13 C12 -63.6(9) . . . 2_655 ? N2 Cu1 N4 C18 135.1(16) . . . . ? N5 Cu1 N4 C18 174.8(15) . . . . ? N1 Cu1 N4 C18 7.1(15) . . . . ? Cl1 Cu1 N4 C18 -83.7(14) . . . . ? N2 Cu1 N4 C14 -48.3(16) . . . . ? N5 Cu1 N4 C14 -8.6(8) . . . . ? N1 Cu1 N4 C14 -176.4(8) . . . . ? Cl1 Cu1 N4 C14 92.9(8) . . . . ? C18 N4 C14 C15 0.9(19) . . . . ? Cu1 N4 C14 C15 -176.0(9) . . . . ? C18 N4 C14 C19 -178.0(13) . . . . ? Cu1 N4 C14 C19 5.1(12) . . . . ? N4 C14 C15 C16 -2(2) . . . . ? C19 C14 C15 C16 177.0(14) . . . . ? C14 C15 C16 C17 0(3) . . . . ? C15 C16 C17 C18 3(3) . . . . ? C14 N4 C18 C17 2(3) . . . . ? Cu1 N4 C18 C17 178.4(14) . . . . ? C16 C17 C18 N4 -4(3) . . . . ? C25 N5 C19 N6 -0.7(12) . . . . ? Cu1 N5 C19 N6 171.7(7) . . . . ? C25 N5 C19 C14 176.1(9) . . . . ? Cu1 N5 C19 C14 -11.5(12) . . . . ? N4 C14 C19 N5 4.0(14) . . . . ? C15 C14 C19 N5 -174.8(11) . . . . ? N4 C14 C19 N6 179.8(11) . . . . ? C15 C14 C19 N6 1(2) . . . . ? N5 C19 N6 C24 2.1(12) . . . . ? C14 C19 N6 C24 -174.0(11) . . . . ? N5 C19 N6 C20 -178.8(12) . . . . ? C14 C19 N6 C20 5(2) . . . . ? C24 N6 C20 C21 -4(2) . . . . ? C19 N6 C20 C21 176.7(15) . . . . ? N6 C20 C21 C22 2(3) . . . . ? C20 C21 C22 C23 0(3) . . . . ? C21 C22 C23 C24 -1(3) . . . . ? C19 N6 C24 C25 -2.8(13) . . . . ? C20 N6 C24 C25 178.0(11) . . . . ? C19 N6 C24 C23 -177.2(13) . . . . ? C20 N6 C24 C23 3.6(19) . . . . ? C22 C23 C24 N6 -1(3) . . . . ? C22 C23 C24 C25 -173.8(17) . . . . ? C19 N5 C25 C24 -1.1(12) . . . . ? Cu1 N5 C25 C24 -171.2(8) . . . . ? C19 N5 C25 C13 -175.7(9) . . . . ? Cu1 N5 C25 C13 14.2(15) . . . . ? N6 C24 C25 N5 2.4(12) . . . . ? C23 C24 C25 N5 175.5(16) . . . . ? N6 C24 C25 C13 176.9(9) . . . . ? C23 C24 C25 C13 -10(2) . . . . ? C25 C13 C25 N5 110.6(11) 2_655 . . . ? C12 C13 C25 N5 -127.9(9) 2_655 . . . ? C12 C13 C25 N5 -8.0(13) . . . . ? C25 C13 C25 C24 -62.8(10) 2_655 . . . ? C12 C13 C25 C24 58.7(13) 2_655 . . . ? C12 C13 C25 C24 178.6(10) . . . . ? Cl4 Cu3 Cl2 Cu2 -18.1(9) . . . . ? Cl3 Cu2 Cl2 Cu3 -148.1(19) . . . . ? Cu2 Cu2 Cl2 Cu3 -2.4(4) 2 . . . ? Cl2 Cu2 Cl3 Cu2 150(2) . . . 2 ? Cl2 Cu3 Cl4 Cu3 17.7(8) . . . 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 C4 H4 O1 0.93 2.70 3.47(4) 141.2 3_565 O1 H1 Cl1 0.82 2.56 3.24(3) 141.0 . O1B H1B Cl1 0.82 2.65 3.12(4) 117.9 . C4 H4 O1B 0.93 2.68 3.48(6) 145.5 3_565 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.944 _refine_diff_density_min -1.008 _refine_diff_density_rms 0.121 data_t _database_code_depnum_ccdc_archive 'CCDC 889293' #TrackingRef 'Cu2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C50 H34 Cl2 Cu2 N12' _chemical_formula_sum 'C50 H34 Cl2 Cu2 N12' _chemical_formula_weight 1000.87 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' 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_space_group_name_Hall '-P 2yn' 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 10.271(4) _cell_length_b 17.067(6) _cell_length_c 12.280(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.220(9) _cell_angle_gamma 90.00 _cell_volume 2152.3(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 311 _cell_measurement_theta_min 2.307 _cell_measurement_theta_max 16.098 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1020 _exptl_absorpt_coefficient_mu 1.166 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8445 _exptl_absorpt_correction_T_max 0.8727 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12598 _diffrn_reflns_av_R_equivalents 0.0911 _diffrn_reflns_av_sigmaI/netI 0.1041 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4225 _reflns_number_gt 2062 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4225 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1336 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1279 _refine_ls_wR_factor_gt 0.0973 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.72971(6) 0.10419(3) 0.56936(5) 0.0505(2) Uani 1 1 d . . . Cl1 Cl 0.70510(16) 0.22835(7) 0.55841(11) 0.0733(5) Uani 1 1 d . . . C2 C 1.0023(5) 0.1087(3) 0.4395(4) 0.0527(13) Uani 1 1 d . . . H2 H 0.9672 0.1085 0.5087 0.063 Uiso 1 1 calc R . . C22 C 0.4281(6) -0.1742(3) 0.8255(4) 0.0760(18) Uani 1 1 d . . . H22 H 0.3737 -0.2176 0.8306 0.091 Uiso 1 1 calc R . . C17 C 0.8924(6) 0.1497(3) 1.0025(5) 0.0724(17) Uani 1 1 d . . . H17 H 0.9438 0.1773 1.0525 0.087 Uiso 1 1 calc R . . N3 N 0.8031(4) -0.0546(2) 0.3168(3) 0.0413(9) Uani 1 1 d . . . N2 N 0.7573(4) 0.0200(2) 0.4571(3) 0.0416(9) Uani 1 1 d . . . N5 N 0.6557(3) 0.0278(2) 0.6803(3) 0.0396(9) Uani 1 1 d . . . N6 N 0.5913(4) -0.0462(2) 0.8160(3) 0.0416(10) Uani 1 1 d . . . N1 N 1.0059(4) 0.0563(2) 0.2593(3) 0.0510(11) Uani 1 1 d . . . N4 N 0.7731(5) 0.0343(3) 0.9581(3) 0.0784(15) Uani 1 1 d . . . C19 C 0.6633(4) 0.0173(3) 0.7880(4) 0.0412(11) Uani 1 1 d . . . C24 C 0.5341(4) -0.0759(3) 0.7204(3) 0.0417(11) Uani 1 1 d . . . C6 C 0.8421(4) 0.0091(3) 0.3776(4) 0.0406(11) Uani 1 1 d . . . C13 C 0.5462(4) -0.0346(3) 0.5188(3) 0.0398(11) Uani 1 1 d . . . H13 H 0.4989 -0.0838 0.5063 0.048 Uiso 1 1 calc R . . C7 C 0.8562(5) -0.0895(3) 0.2264(4) 0.0541(14) Uani 1 1 d . . . H7 H 0.9339 -0.0711 0.1985 0.065 Uiso 1 1 calc R . . C12 C 0.6644(4) -0.0357(3) 0.4485(3) 0.0375(11) Uani 1 1 d . . . C16 C 0.8608(5) 0.1810(3) 0.9054(4) 0.0616(15) Uani 1 1 d . . . H16 H 0.8906 0.2306 0.8867 0.074 Uiso 1 1 calc R . . C1 C 0.9539(4) 0.0591(3) 0.3585(4) 0.0428(12) Uani 1 1 d . . . C9 C 0.6759(5) -0.1799(3) 0.2201(4) 0.0611(15) Uani 1 1 d . . . H9 H 0.6340 -0.2216 0.1854 0.073 Uiso 1 1 calc R . . C23 C 0.4499(5) -0.1405(3) 0.7271(4) 0.0539(13) Uani 1 1 d . . . H23 H 0.4092 -0.1602 0.6645 0.065 Uiso 1 1 calc R . . C25 C 0.5779(4) -0.0293(3) 0.6377(3) 0.0396(11) Uani 1 1 d . . . C14 C 0.7420(4) 0.0656(3) 0.8628(4) 0.0419(11) Uani 1 1 d . . . C11 C 0.6875(4) -0.0831(3) 0.3607(4) 0.0435(12) Uani 1 1 d . . . C21 C 0.4891(6) -0.1424(3) 0.9199(4) 0.0745(18) Uani 1 1 d . . . H21 H 0.4728 -0.1651 0.9871 0.089 Uiso 1 1 calc R . . C10 C 0.6244(5) -0.1469(3) 0.3103(4) 0.0521(13) Uani 1 1 d . . . H10 H 0.5477 -0.1666 0.3385 0.062 Uiso 1 1 calc R . . C4 C 1.1539(5) 0.1570(3) 0.3126(5) 0.0597(15) Uani 1 1 d . . . H4 H 1.2217 0.1904 0.2946 0.072 Uiso 1 1 calc R . . C20 C 0.5690(5) -0.0810(3) 0.9163(4) 0.0594(15) Uani 1 1 d . . . H20 H 0.6091 -0.0619 0.9795 0.071 Uiso 1 1 calc R . . C8 C 0.7941(6) -0.1500(3) 0.1795(4) 0.0659(16) Uani 1 1 d . . . H8 H 0.8297 -0.1732 0.1184 0.079 Uiso 1 1 calc R . . C15 C 0.7837(5) 0.1386(3) 0.8337(4) 0.0597(15) Uani 1 1 d . . . H15 H 0.7602 0.1594 0.7662 0.072 Uiso 1 1 calc R . . C5 C 1.1024(5) 0.1060(3) 0.2386(4) 0.0562(13) Uani 1 1 d . . . H5 H 1.1366 0.1057 0.1690 0.067 Uiso 1 1 calc R . . C3 C 1.1029(5) 0.1578(3) 0.4146(4) 0.0590(15) Uani 1 1 d . . . H3 H 1.1366 0.1918 0.4673 0.071 Uiso 1 1 calc R . . C18 C 0.8477(7) 0.0766(4) 1.0266(5) 0.095(2) Uani 1 1 d . . . H18 H 0.8702 0.0552 1.0940 0.114 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0546(4) 0.0425(4) 0.0542(4) -0.0040(3) -0.0050(3) -0.0023(3) Cl1 0.1138(13) 0.0419(8) 0.0642(9) 0.0085(7) 0.0038(8) 0.0032(8) C2 0.050(3) 0.054(3) 0.054(3) -0.004(3) 0.000(2) 0.002(3) C22 0.101(5) 0.070(4) 0.057(4) 0.010(3) 0.007(3) -0.037(4) C17 0.082(4) 0.075(4) 0.059(4) -0.010(3) -0.032(3) -0.005(4) N3 0.044(2) 0.041(2) 0.039(2) -0.0094(19) 0.0018(19) 0.003(2) N2 0.042(2) 0.044(2) 0.038(2) -0.0017(18) -0.0041(19) 0.001(2) N5 0.042(2) 0.046(2) 0.031(2) 0.0003(17) -0.0074(17) -0.0023(19) N6 0.048(2) 0.043(2) 0.034(2) 0.0008(18) -0.0020(19) -0.001(2) N1 0.048(3) 0.060(3) 0.044(3) 0.003(2) 0.001(2) -0.002(2) N4 0.111(4) 0.072(3) 0.051(3) 0.007(2) -0.033(3) -0.027(3) C19 0.041(3) 0.044(3) 0.038(3) 0.002(2) -0.005(2) -0.002(2) C24 0.042(3) 0.045(3) 0.038(3) 0.002(2) -0.002(2) -0.001(2) C6 0.038(3) 0.042(3) 0.042(3) 0.000(2) -0.001(2) 0.002(2) C13 0.038(3) 0.045(3) 0.037(3) 0.001(2) -0.006(2) 0.000(2) C7 0.060(3) 0.053(3) 0.049(3) -0.011(3) 0.012(3) 0.000(3) C12 0.036(3) 0.039(3) 0.037(3) -0.002(2) -0.009(2) 0.000(2) C16 0.074(4) 0.044(3) 0.066(4) -0.006(3) -0.015(3) -0.010(3) C1 0.044(3) 0.037(3) 0.047(3) -0.001(2) -0.006(2) 0.008(2) C9 0.070(4) 0.048(3) 0.065(4) -0.019(3) 0.002(3) -0.009(3) C23 0.062(4) 0.053(3) 0.047(3) -0.005(3) -0.002(3) -0.011(3) C25 0.035(3) 0.046(3) 0.038(3) 0.005(2) -0.006(2) 0.002(2) C14 0.048(3) 0.037(3) 0.040(3) -0.001(2) -0.008(2) 0.003(2) C11 0.041(3) 0.047(3) 0.042(3) -0.002(2) -0.003(2) 0.006(2) C21 0.101(5) 0.076(4) 0.046(4) 0.006(3) 0.007(3) -0.027(4) C10 0.057(3) 0.051(3) 0.048(3) -0.008(2) -0.006(3) -0.002(3) C4 0.040(3) 0.063(4) 0.075(4) 0.006(3) -0.003(3) -0.007(3) C20 0.080(4) 0.062(4) 0.036(3) 0.007(3) -0.001(3) -0.012(3) C8 0.078(4) 0.066(4) 0.055(3) -0.018(3) 0.012(3) 0.000(3) C15 0.073(4) 0.055(3) 0.050(3) 0.000(3) -0.017(3) -0.006(3) C5 0.047(3) 0.065(4) 0.057(3) 0.013(3) 0.002(3) 0.003(3) C3 0.054(3) 0.056(4) 0.067(4) -0.012(3) -0.005(3) -0.002(3) C18 0.140(6) 0.077(5) 0.065(4) 0.017(3) -0.055(4) -0.034(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 2.016(4) . ? Cu1 N5 2.043(3) . ? Cu1 Cl1 2.1379(16) . ? C2 C3 1.370(6) . ? C2 C1 1.390(6) . ? C22 C23 1.361(6) . ? C22 C21 1.415(7) . ? C17 C16 1.340(7) . ? C17 C18 1.363(7) . ? N3 C6 1.373(5) . ? N3 C7 1.382(5) . ? N3 C11 1.401(5) . ? N2 C6 1.335(5) . ? N2 C12 1.349(5) . ? N5 C19 1.336(5) . ? N5 C25 1.358(5) . ? N6 C19 1.362(5) . ? N6 C20 1.391(5) . ? N6 C24 1.397(5) . ? N1 C5 1.334(6) . ? N1 C1 1.340(5) . ? N4 C14 1.320(5) . ? N4 C18 1.338(6) . ? C19 C14 1.464(6) . ? C24 C25 1.373(6) . ? C24 C23 1.405(6) . ? C6 C1 1.455(6) . ? C13 C25 1.492(5) . ? C13 C12 1.505(6) . ? C13 C13 1.578(8) 3_656 ? C7 C8 1.337(7) . ? C12 C11 1.372(6) . ? C16 C15 1.377(6) . ? C9 C10 1.359(6) . ? C9 C8 1.418(7) . ? C14 C15 1.367(6) . ? C11 C10 1.405(6) . ? C21 C20 1.332(7) . ? C4 C5 1.359(7) . ? C4 C3 1.368(7) . ? 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 N2 Cu1 N5 93.48(15) . . ? N2 Cu1 Cl1 132.98(11) . . ? N5 Cu1 Cl1 128.97(11) . . ? C3 C2 C1 118.2(5) . . ? C23 C22 C21 119.1(5) . . ? C16 C17 C18 118.8(5) . . ? C6 N3 C7 131.5(4) . . ? C6 N3 C11 107.7(4) . . ? C7 N3 C11 120.8(4) . . ? C6 N2 C12 108.4(4) . . ? C6 N2 Cu1 134.7(3) . . ? C12 N2 Cu1 116.5(3) . . ? C19 N5 C25 107.9(4) . . ? C19 N5 Cu1 137.0(3) . . ? C25 N5 Cu1 115.2(3) . . ? C19 N6 C20 131.7(4) . . ? C19 N6 C24 107.3(3) . . ? C20 N6 C24 121.1(4) . . ? C5 N1 C1 117.6(4) . . ? C14 N4 C18 117.6(5) . . ? N5 C19 N6 109.7(4) . . ? N5 C19 C14 124.5(4) . . ? N6 C19 C14 125.8(4) . . ? C25 C24 N6 105.9(4) . . ? C25 C24 C23 135.2(4) . . ? N6 C24 C23 118.9(4) . . ? N2 C6 N3 108.7(4) . . ? N2 C6 C1 124.5(4) . . ? N3 C6 C1 126.8(4) . . ? C25 C13 C12 113.6(4) . . ? C25 C13 C13 110.9(4) . 3_656 ? C12 C13 C13 109.2(4) . 3_656 ? C8 C7 N3 119.1(5) . . ? N2 C12 C11 110.0(4) . . ? N2 C12 C13 121.6(4) . . ? C11 C12 C13 127.9(4) . . ? C17 C16 C15 118.9(5) . . ? N1 C1 C2 121.9(4) . . ? N1 C1 C6 117.2(4) . . ? C2 C1 C6 120.9(4) . . ? C10 C9 C8 119.2(5) . . ? C22 C23 C24 119.8(5) . . ? N5 C25 C24 109.3(4) . . ? N5 C25 C13 122.3(4) . . ? C24 C25 C13 128.3(4) . . ? N4 C14 C15 122.0(4) . . ? N4 C14 C19 116.6(4) . . ? C15 C14 C19 121.4(4) . . ? C12 C11 N3 105.1(4) . . ? C12 C11 C10 135.8(5) . . ? N3 C11 C10 119.1(4) . . ? C20 C21 C22 122.5(5) . . ? C9 C10 C11 119.8(5) . . ? C5 C4 C3 117.9(5) . . ? C21 C20 N6 118.5(5) . . ? C7 C8 C9 122.1(5) . . ? C14 C15 C16 119.4(5) . . ? N1 C5 C4 124.1(5) . . ? C4 C3 C2 120.2(5) . . ? N4 C18 C17 123.3(5) . . ? 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 N5 Cu1 N2 C6 -149.8(4) . . . . ? Cl1 Cu1 N2 C6 53.6(5) . . . . ? N5 Cu1 N2 C12 38.7(3) . . . . ? Cl1 Cu1 N2 C12 -117.9(3) . . . . ? N2 Cu1 N5 C19 141.2(4) . . . . ? Cl1 Cu1 N5 C19 -60.7(5) . . . . ? N2 Cu1 N5 C25 -38.1(3) . . . . ? Cl1 Cu1 N5 C25 120.0(3) . . . . ? C25 N5 C19 N6 0.1(5) . . . . ? Cu1 N5 C19 N6 -179.3(3) . . . . ? C25 N5 C19 C14 177.9(4) . . . . ? Cu1 N5 C19 C14 -1.5(7) . . . . ? C20 N6 C19 N5 179.5(4) . . . . ? C24 N6 C19 N5 -1.1(5) . . . . ? C20 N6 C19 C14 1.8(8) . . . . ? C24 N6 C19 C14 -178.8(4) . . . . ? C19 N6 C24 C25 1.6(5) . . . . ? C20 N6 C24 C25 -178.9(4) . . . . ? C19 N6 C24 C23 -177.6(4) . . . . ? C20 N6 C24 C23 1.9(6) . . . . ? C12 N2 C6 N3 0.1(5) . . . . ? Cu1 N2 C6 N3 -171.9(3) . . . . ? C12 N2 C6 C1 178.2(4) . . . . ? Cu1 N2 C6 C1 6.2(7) . . . . ? C7 N3 C6 N2 179.6(4) . . . . ? C11 N3 C6 N2 0.9(5) . . . . ? C7 N3 C6 C1 1.6(8) . . . . ? C11 N3 C6 C1 -177.1(4) . . . . ? C6 N3 C7 C8 -177.1(5) . . . . ? C11 N3 C7 C8 1.5(7) . . . . ? C6 N2 C12 C11 -1.0(5) . . . . ? Cu1 N2 C12 C11 172.6(3) . . . . ? C6 N2 C12 C13 -173.4(4) . . . . ? Cu1 N2 C12 C13 0.3(5) . . . . ? C25 C13 C12 N2 -53.1(6) . . . . ? C13 C13 C12 N2 71.4(6) 3_656 . . . ? C25 C13 C12 C11 136.1(5) . . . . ? C13 C13 C12 C11 -99.5(6) 3_656 . . . ? C18 C17 C16 C15 0.5(9) . . . . ? C5 N1 C1 C2 -3.4(7) . . . . ? C5 N1 C1 C6 175.3(4) . . . . ? C3 C2 C1 N1 2.4(7) . . . . ? C3 C2 C1 C6 -176.1(4) . . . . ? N2 C6 C1 N1 -160.0(4) . . . . ? N3 C6 C1 N1 17.8(7) . . . . ? N2 C6 C1 C2 18.6(7) . . . . ? N3 C6 C1 C2 -163.6(4) . . . . ? C21 C22 C23 C24 1.2(8) . . . . ? C25 C24 C23 C22 179.4(5) . . . . ? N6 C24 C23 C22 -1.6(7) . . . . ? C19 N5 C25 C24 0.9(5) . . . . ? Cu1 N5 C25 C24 -179.5(3) . . . . ? C19 N5 C25 C13 179.1(4) . . . . ? Cu1 N5 C25 C13 -1.4(5) . . . . ? N6 C24 C25 N5 -1.5(5) . . . . ? C23 C24 C25 N5 177.5(5) . . . . ? N6 C24 C25 C13 -179.5(4) . . . . ? C23 C24 C25 C13 -0.5(9) . . . . ? C12 C13 C25 N5 53.5(6) . . . . ? C13 C13 C25 N5 -70.0(6) 3_656 . . . ? C12 C13 C25 C24 -128.7(5) . . . . ? C13 C13 C25 C24 107.8(6) 3_656 . . . ? C18 N4 C14 C15 0.0(8) . . . . ? C18 N4 C14 C19 178.3(5) . . . . ? N5 C19 C14 N4 -158.8(5) . . . . ? N6 C19 C14 N4 18.5(7) . . . . ? N5 C19 C14 C15 19.6(7) . . . . ? N6 C19 C14 C15 -163.1(5) . . . . ? N2 C12 C11 N3 1.6(5) . . . . ? C13 C12 C11 N3 173.3(4) . . . . ? N2 C12 C11 C10 -177.4(5) . . . . ? C13 C12 C11 C10 -5.6(9) . . . . ? C6 N3 C11 C12 -1.5(5) . . . . ? C7 N3 C11 C12 179.6(4) . . . . ? C6 N3 C11 C10 177.6(4) . . . . ? C7 N3 C11 C10 -1.2(6) . . . . ? C23 C22 C21 C20 -1.0(10) . . . . ? C8 C9 C10 C11 1.1(8) . . . . ? C12 C11 C10 C9 178.7(5) . . . . ? N3 C11 C10 C9 -0.1(7) . . . . ? C22 C21 C20 N6 1.2(9) . . . . ? C19 N6 C20 C21 177.7(5) . . . . ? C24 N6 C20 C21 -1.6(7) . . . . ? N3 C7 C8 C9 -0.4(8) . . . . ? C10 C9 C8 C7 -0.9(9) . . . . ? N4 C14 C15 C16 0.3(8) . . . . ? C19 C14 C15 C16 -178.0(5) . . . . ? C17 C16 C15 C14 -0.5(8) . . . . ? C1 N1 C5 C4 2.4(7) . . . . ? C3 C4 C5 N1 -0.5(8) . . . . ? C5 C4 C3 C2 -0.6(7) . . . . ? C1 C2 C3 C4 -0.4(7) . . . . ? C14 N4 C18 C17 0.0(10) . . . . ? C16 C17 C18 N4 -0.2(11) . . . . ? 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 C7 H7 N1 0.93 2.41 2.948(7) 116.8 . C18 H18 N1 0.93 2.44 3.276(7) 149.9 1_556 C20 H20 N4 0.93 2.37 2.912(7) 117.0 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.355 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.069 data_CCDC915885 _database_code_depnum_ccdc_archive 'CCDC 915885' #TrackingRef '17092_web_deposit_cif_file_0_YanmeiChen_1358858309.CCDC 915885.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H18 Cl2 N6 Zn' _chemical_formula_sum 'C25 H18 Cl2 N6 Zn' _chemical_formula_weight 538.72 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8615(6) _cell_length_b 10.7668(8) _cell_length_c 14.0784(10) _cell_angle_alpha 73.4730(10) _cell_angle_beta 84.730(2) _cell_angle_gamma 89.3540(10) _cell_volume 1137.44(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3196 _cell_measurement_theta_min 2.602 _cell_measurement_theta_max 26.883 _exptl_crystal_description bolck _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 1.342 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7050 _exptl_absorpt_correction_T_max 0.7751 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6233 _diffrn_reflns_av_R_equivalents 0.0144 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3923 _reflns_number_gt 3424 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. During the refinement, the command 'omit -2 50' was used to omit the weak reflections above 50 degree. ; _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^)+(0.0569P)^2^+0.7031P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3923 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.1106 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.005 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 Zn1 Zn 0.33242(5) 0.16889(3) 0.64042(2) 0.04415(14) Uani 1 1 d . . . Cl1 Cl 0.17459(14) -0.00312(9) 0.65904(9) 0.0778(3) Uani 1 1 d . . . Cl2 Cl 0.55267(14) 0.14756(10) 0.73017(7) 0.0726(3) Uani 1 1 d . . . C18 C 0.3929(5) 0.6957(4) 1.0775(3) 0.0573(9) Uani 1 1 d . . . H18 H 0.4456 0.6897 1.1352 0.069 Uiso 1 1 calc R . . N2 N 0.2149(3) 0.3407(2) 0.63079(17) 0.0371(5) Uani 1 1 d . . . C23 C 0.1489(4) 0.1389(3) 1.0111(3) 0.0555(8) Uani 1 1 d . . . H23 H 0.1140 0.0830 0.9767 0.067 Uiso 1 1 calc R . . N4 N 0.3400(4) 0.5853(3) 1.0624(2) 0.0503(6) Uani 1 1 d . . . N3 N 0.1768(3) 0.5425(2) 0.54502(18) 0.0395(5) Uani 1 1 d . . . N6 N 0.2148(3) 0.3540(2) 1.01830(18) 0.0423(6) Uani 1 1 d . . . C14 C 0.2635(4) 0.5962(3) 0.9792(2) 0.0416(7) Uani 1 1 d . . . N5 N 0.1500(3) 0.4801(3) 0.87152(18) 0.0472(6) Uani 1 1 d . . . C19 C 0.2087(4) 0.4791(3) 0.9575(2) 0.0416(7) Uani 1 1 d . . . C24 C 0.1561(4) 0.2731(3) 0.9646(2) 0.0432(7) Uani 1 1 d . . . N1 N 0.4056(3) 0.2680(2) 0.49228(17) 0.0407(5) Uani 1 1 d . . . C13 C 0.0429(5) 0.3191(4) 0.7927(2) 0.0580(9) Uani 1 1 d . . . H13A H 0.0615 0.2277 0.8004 0.070 Uiso 1 1 calc R . . H13B H -0.0795 0.3318 0.7992 0.070 Uiso 1 1 calc R . . C5 C 0.4974(4) 0.2201(3) 0.4264(2) 0.0527(8) Uani 1 1 d . . . H5 H 0.5296 0.1339 0.4466 0.063 Uiso 1 1 calc R . . C6 C 0.2531(3) 0.4292(3) 0.5425(2) 0.0351(6) Uani 1 1 d . . . C10 C -0.0021(4) 0.6271(4) 0.6613(3) 0.0585(9) Uani 1 1 d . . . H10 H -0.0604 0.6156 0.7238 0.070 Uiso 1 1 calc R . . C25 C 0.1192(4) 0.3549(3) 0.8755(2) 0.0474(7) Uani 1 1 d . . . C11 C 0.0870(4) 0.5225(3) 0.6384(2) 0.0445(7) Uani 1 1 d . . . C7 C 0.1774(4) 0.6633(3) 0.4751(3) 0.0518(8) Uani 1 1 d . . . H7 H 0.2375 0.6773 0.4129 0.062 Uiso 1 1 calc R . . C1 C 0.3584(3) 0.3931(3) 0.4638(2) 0.0355(6) Uani 1 1 d . . . C9 C -0.0020(5) 0.7423(4) 0.5928(4) 0.0698(12) Uani 1 1 d . . . H9 H -0.0623 0.8105 0.6072 0.084 Uiso 1 1 calc R . . C21 C 0.2487(5) 0.1749(4) 1.1558(3) 0.0650(10) Uani 1 1 d . . . H21 H 0.2781 0.1408 1.2205 0.078 Uiso 1 1 calc R . . C15 C 0.2365(4) 0.7154(3) 0.9112(2) 0.0489(7) Uani 1 1 d . . . H15 H 0.1805 0.7202 0.8549 0.059 Uiso 1 1 calc R . . C12 C 0.1132(4) 0.3945(3) 0.6900(2) 0.0402(6) Uani 1 1 d . . . C2 C 0.4083(4) 0.4713(3) 0.3687(2) 0.0463(7) Uani 1 1 d . . . H2 H 0.3786 0.5582 0.3498 0.056 Uiso 1 1 calc R . . C3 C 0.5028(4) 0.4182(4) 0.3026(2) 0.0575(9) Uani 1 1 d . . . H3 H 0.5366 0.4693 0.2385 0.069 Uiso 1 1 calc R . . C4 C 0.5464(5) 0.2914(4) 0.3312(3) 0.0600(9) Uani 1 1 d . . . H4 H 0.6080 0.2541 0.2870 0.072 Uiso 1 1 calc R . . C20 C 0.2614(4) 0.3034(3) 1.1140(2) 0.0518(8) Uani 1 1 d . . . H20 H 0.3008 0.3574 1.1486 0.062 Uiso 1 1 calc R . . C17 C 0.3746(5) 0.8159(4) 1.0142(3) 0.0587(9) Uani 1 1 d . . . H17 H 0.4152 0.8891 1.0280 0.070 Uiso 1 1 calc R . . C8 C 0.0884(5) 0.7603(3) 0.4997(3) 0.0659(11) Uani 1 1 d . . . H8 H 0.0877 0.8412 0.4530 0.079 Uiso 1 1 calc R . . C22 C 0.1921(5) 0.0900(4) 1.1050(3) 0.0654(10) Uani 1 1 d . . . H22 H 0.1846 0.0013 1.1358 0.078 Uiso 1 1 calc R . . C16 C 0.2949(5) 0.8267(3) 0.9293(3) 0.0603(9) Uani 1 1 d . . . H16 H 0.2804 0.9076 0.8847 0.072 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 Zn1 0.0580(2) 0.0358(2) 0.0384(2) -0.00946(15) -0.00685(16) 0.00045(15) Cl1 0.0865(7) 0.0394(5) 0.1055(8) -0.0109(5) -0.0286(6) -0.0090(4) Cl2 0.0827(7) 0.0680(6) 0.0632(6) -0.0044(5) -0.0329(5) 0.0008(5) C18 0.060(2) 0.060(2) 0.059(2) -0.0301(18) -0.0018(17) -0.0025(17) N2 0.0422(13) 0.0383(13) 0.0336(12) -0.0138(10) -0.0062(10) -0.0019(10) C23 0.0527(19) 0.0476(19) 0.070(2) -0.0253(17) 0.0037(17) -0.0040(15) N4 0.0569(16) 0.0482(15) 0.0497(15) -0.0210(13) -0.0017(13) -0.0010(12) N3 0.0368(12) 0.0376(13) 0.0492(14) -0.0175(11) -0.0132(11) 0.0017(10) N6 0.0423(13) 0.0456(14) 0.0413(13) -0.0186(11) 0.0035(11) 0.0025(11) C14 0.0404(15) 0.0458(17) 0.0407(16) -0.0190(13) 0.0062(13) 0.0011(13) N5 0.0499(15) 0.0564(16) 0.0374(13) -0.0183(12) 0.0018(11) -0.0049(12) C19 0.0412(16) 0.0493(17) 0.0365(15) -0.0181(13) 0.0041(12) -0.0001(13) C24 0.0393(15) 0.0470(17) 0.0455(16) -0.0202(14) 0.0081(13) -0.0043(13) N1 0.0444(13) 0.0426(14) 0.0365(12) -0.0139(11) -0.0033(10) 0.0046(11) C13 0.057(2) 0.072(2) 0.0515(19) -0.0325(18) 0.0106(16) -0.0194(17) C5 0.061(2) 0.0555(19) 0.0458(18) -0.0210(15) -0.0066(15) 0.0152(16) C6 0.0380(14) 0.0360(14) 0.0337(14) -0.0121(12) -0.0088(11) -0.0008(11) C10 0.0448(18) 0.069(2) 0.079(2) -0.046(2) -0.0166(17) 0.0100(16) C25 0.0459(17) 0.058(2) 0.0425(17) -0.0248(15) 0.0068(13) -0.0091(14) C11 0.0364(15) 0.0519(18) 0.0548(18) -0.0292(15) -0.0087(13) 0.0004(13) C7 0.0550(19) 0.0392(17) 0.062(2) -0.0098(15) -0.0260(16) 0.0027(14) C1 0.0344(14) 0.0395(15) 0.0345(14) -0.0120(12) -0.0070(11) -0.0043(11) C9 0.052(2) 0.064(2) 0.117(4) -0.055(3) -0.036(2) 0.0203(18) C21 0.076(3) 0.054(2) 0.061(2) -0.0109(18) -0.0065(19) 0.0076(18) C15 0.0526(18) 0.0487(18) 0.0443(17) -0.0137(14) 0.0024(14) 0.0040(14) C12 0.0399(15) 0.0486(17) 0.0377(15) -0.0213(13) -0.0036(12) -0.0054(13) C2 0.0495(17) 0.0457(17) 0.0399(16) -0.0047(13) -0.0081(13) -0.0048(14) C3 0.053(2) 0.080(3) 0.0346(16) -0.0110(16) 0.0016(14) -0.0072(18) C4 0.056(2) 0.083(3) 0.0455(19) -0.0283(18) -0.0001(16) 0.0098(18) C20 0.060(2) 0.0513(19) 0.0445(17) -0.0141(15) -0.0061(15) 0.0070(15) C17 0.062(2) 0.052(2) 0.068(2) -0.0284(18) 0.0027(18) -0.0054(16) C8 0.064(2) 0.0426(19) 0.099(3) -0.024(2) -0.036(2) 0.0118(17) C22 0.071(2) 0.049(2) 0.072(3) -0.0109(18) -0.005(2) 0.0027(18) C16 0.069(2) 0.0416(18) 0.065(2) -0.0116(16) 0.0091(18) 0.0038(16) _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 Zn1 N2 2.034(2) . ? Zn1 N1 2.085(2) . ? Zn1 Cl1 2.1804(10) . ? Zn1 Cl2 2.2080(10) . ? C18 N4 1.343(4) . ? C18 C17 1.361(5) . ? C18 H18 0.9300 . ? N2 C6 1.344(4) . ? N2 C12 1.346(4) . ? C23 C22 1.350(5) . ? C23 C24 1.406(5) . ? C23 H23 0.9300 . ? N4 C14 1.340(4) . ? N3 C6 1.362(4) . ? N3 C7 1.389(4) . ? N3 C11 1.394(4) . ? N6 C19 1.378(4) . ? N6 C20 1.384(4) . ? N6 C24 1.411(4) . ? C14 C15 1.393(4) . ? C14 C19 1.457(4) . ? N5 C19 1.332(4) . ? N5 C25 1.357(4) . ? C24 C25 1.366(5) . ? N1 C5 1.336(4) . ? N1 C1 1.350(4) . ? C13 C12 1.500(4) . ? C13 C25 1.502(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C5 C4 1.364(5) . ? C5 H5 0.9300 . ? C6 C1 1.461(4) . ? C10 C9 1.338(6) . ? C10 C11 1.418(5) . ? C10 H10 0.9300 . ? C11 C12 1.387(4) . ? C7 C8 1.359(5) . ? C7 H7 0.9300 . ? C1 C2 1.387(4) . ? C9 C8 1.396(6) . ? C9 H9 0.9300 . ? C21 C20 1.341(5) . ? C21 C22 1.409(6) . ? C21 H21 0.9300 . ? C15 C16 1.385(5) . ? C15 H15 0.9300 . ? C2 C3 1.383(5) . ? C2 H2 0.9300 . ? C3 C4 1.359(5) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C20 H20 0.9300 . ? C17 C16 1.375(5) . ? C17 H17 0.9300 . ? C8 H8 0.9300 . ? C22 H22 0.9300 . ? C16 H16 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Zn1 N1 79.71(9) . . ? N2 Zn1 Cl1 118.56(7) . . ? N1 Zn1 Cl1 113.78(8) . . ? N2 Zn1 Cl2 111.04(7) . . ? N1 Zn1 Cl2 110.48(7) . . ? Cl1 Zn1 Cl2 117.33(4) . . ? N4 C18 C17 124.3(3) . . ? N4 C18 H18 117.8 . . ? C17 C18 H18 117.8 . . ? C6 N2 C12 109.2(2) . . ? C6 N2 Zn1 112.83(18) . . ? C12 N2 Zn1 137.9(2) . . ? C22 C23 C24 120.8(3) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C14 N4 C18 116.9(3) . . ? C6 N3 C7 132.0(3) . . ? C6 N3 C11 107.7(2) . . ? C7 N3 C11 120.3(3) . . ? C19 N6 C20 132.3(3) . . ? C19 N6 C24 106.4(2) . . ? C20 N6 C24 121.2(3) . . ? N4 C14 C15 122.6(3) . . ? N4 C14 C19 119.1(3) . . ? C15 C14 C19 118.3(3) . . ? C19 N5 C25 106.9(3) . . ? N5 C19 N6 110.4(3) . . ? N5 C19 C14 123.0(3) . . ? N6 C19 C14 126.6(3) . . ? C25 C24 C23 137.0(3) . . ? C25 C24 N6 105.3(3) . . ? C23 C24 N6 117.7(3) . . ? C5 N1 C1 118.8(3) . . ? C5 N1 Zn1 126.1(2) . . ? C1 N1 Zn1 115.10(18) . . ? C12 C13 C25 114.8(3) . . ? C12 C13 H13A 108.6 . . ? C25 C13 H13A 108.6 . . ? C12 C13 H13B 108.6 . . ? C25 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? N1 C5 C4 123.3(3) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? N2 C6 N3 108.6(2) . . ? N2 C6 C1 119.8(2) . . ? N3 C6 C1 131.6(3) . . ? C9 C10 C11 119.8(4) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? N5 C25 C24 111.0(3) . . ? N5 C25 C13 121.8(3) . . ? C24 C25 C13 127.1(3) . . ? C12 C11 N3 106.1(2) . . ? C12 C11 C10 134.7(3) . . ? N3 C11 C10 119.2(3) . . ? C8 C7 N3 118.6(4) . . ? C8 C7 H7 120.7 . . ? N3 C7 H7 120.7 . . ? N1 C1 C2 120.5(3) . . ? N1 C1 C6 112.2(2) . . ? C2 C1 C6 127.3(3) . . ? C10 C9 C8 120.2(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C20 C21 C22 122.2(4) . . ? C20 C21 H21 118.9 . . ? C22 C21 H21 118.9 . . ? C16 C15 C14 118.6(3) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? N2 C12 C11 108.4(3) . . ? N2 C12 C13 122.3(3) . . ? C11 C12 C13 129.3(3) . . ? C1 C2 C3 119.0(3) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 120.1(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 118.3(3) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? C21 C20 N6 118.7(3) . . ? C21 C20 H20 120.6 . . ? N6 C20 H20 120.6 . . ? C18 C17 C16 118.6(3) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? C7 C8 C9 122.0(4) . . ? C7 C8 H8 119.0 . . ? C9 C8 H8 119.0 . . ? C23 C22 C21 119.3(4) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C17 C16 C15 119.0(3) . . ? C17 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.496 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.068 data_CCDC915886 _database_code_depnum_ccdc_archive 'CCDC 915886' #TrackingRef '17093_web_deposit_cif_file_0_YanmeiChen_1358858515.CCDC 915886.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H18 N6' _chemical_formula_sum 'C25 H18 N6' _chemical_formula_weight 402.45 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/c' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 12.8398(18) _cell_length_b 5.1086(7) _cell_length_c 15.192(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.007(3) _cell_angle_gamma 90.00 _cell_volume 962.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1901 _cell_measurement_theta_min 2.776 _cell_measurement_theta_max 28.13 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9695 _exptl_absorpt_correction_T_max 0.9787 _exptl_absorpt_process_details 'SADABS (Bruker, 2005)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6416 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 28.31 _reflns_number_total 2378 _reflns_number_gt 1770 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX-II (Bruker, 2005)' _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0577P)^2^+0.0664P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2378 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.26306(8) 0.44953(18) 0.37281(6) 0.0368(2) Uani 1 1 d . . . C1 C 0.21756(9) 0.0878(2) 0.46986(8) 0.0384(3) Uani 1 1 d . . . N3 N 0.08935(8) 0.3623(2) 0.35895(7) 0.0451(3) Uani 1 1 d . . . N4 N 0.32139(8) 0.0495(2) 0.51305(7) 0.0463(3) Uani 1 1 d . . . C7 C 0.37455(10) 0.4582(3) 0.39619(9) 0.0446(3) Uani 1 1 d . . . H7 H 0.4145 0.3396 0.4380 0.054 Uiso 1 1 calc R . . C6 C 0.19056(9) 0.2939(2) 0.40134(8) 0.0379(3) Uani 1 1 d . . . C11 C 0.20204(10) 0.6246(2) 0.30872(7) 0.0398(3) Uani 1 1 d . . . C10 C 0.25607(11) 0.8139(3) 0.26968(9) 0.0485(3) Uani 1 1 d . . . H10 H 0.2170 0.9325 0.2274 0.058 Uiso 1 1 calc R . . C12 C 0.09540(10) 0.5637(2) 0.30249(8) 0.0444(3) Uani 1 1 d . . . C3 C 0.16107(13) -0.2571(3) 0.55328(10) 0.0588(4) Uani 1 1 d . . . H3 H 0.1073 -0.3586 0.5671 0.071 Uiso 1 1 calc R . . C5 C 0.34373(12) -0.1428(3) 0.57497(9) 0.0529(4) Uani 1 1 d . . . H5 H 0.4156 -0.1724 0.6049 0.063 Uiso 1 1 calc R . . C2 C 0.13516(11) -0.0621(3) 0.48842(9) 0.0497(3) Uani 1 1 d . . . H2 H 0.0637 -0.0312 0.4575 0.060 Uiso 1 1 calc R . . C9 C 0.36515(12) 0.8227(3) 0.29389(9) 0.0526(4) Uani 1 1 d . . . H9 H 0.4011 0.9484 0.2687 0.063 Uiso 1 1 calc R . . C4 C 0.26727(13) -0.2988(3) 0.59699(10) 0.0576(4) Uani 1 1 d . . . H4 H 0.2871 -0.4299 0.6406 0.069 Uiso 1 1 calc R . . C13 C 0.0000 0.7166(4) 0.2500 0.0616(6) Uani 1 2 d S . . H13A H -0.0237 0.8292 0.2925 0.074 Uiso 0.50 1 calc PR . . H13B H 0.0237 0.8292 0.2075 0.074 Uiso 0.50 1 calc PR . . C8 C 0.42440(11) 0.6402(3) 0.35768(10) 0.0525(3) Uani 1 1 d . . . H8 H 0.4993 0.6462 0.3733 0.063 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 N1 0.0335(5) 0.0377(5) 0.0367(5) -0.0018(4) 0.0047(4) 0.0013(4) C1 0.0393(6) 0.0371(6) 0.0378(6) -0.0044(5) 0.0084(5) 0.0007(5) N3 0.0344(5) 0.0434(6) 0.0512(6) -0.0031(5) -0.0002(4) -0.0020(4) N4 0.0420(6) 0.0450(6) 0.0489(6) 0.0041(5) 0.0065(5) 0.0043(5) C7 0.0332(6) 0.0491(7) 0.0499(7) 0.0013(6) 0.0078(5) 0.0029(5) C6 0.0322(6) 0.0379(6) 0.0411(6) -0.0044(5) 0.0047(5) -0.0009(5) C11 0.0414(7) 0.0392(6) 0.0338(6) -0.0038(5) 0.0006(5) 0.0011(5) C10 0.0594(8) 0.0432(7) 0.0387(6) 0.0016(5) 0.0052(6) -0.0017(6) C12 0.0397(7) 0.0391(6) 0.0448(7) -0.0031(5) -0.0064(5) -0.0003(5) C3 0.0687(10) 0.0529(8) 0.0587(8) 0.0007(7) 0.0232(7) -0.0111(7) C5 0.0556(8) 0.0492(8) 0.0496(7) 0.0042(6) 0.0061(6) 0.0108(6) C2 0.0458(7) 0.0525(8) 0.0511(7) -0.0011(6) 0.0131(6) -0.0042(6) C9 0.0579(9) 0.0493(8) 0.0522(8) 0.0024(6) 0.0174(7) -0.0087(6) C4 0.0802(11) 0.0445(7) 0.0488(7) 0.0060(6) 0.0176(7) 0.0058(7) C13 0.0464(11) 0.0477(11) 0.0727(13) 0.000 -0.0172(10) 0.000 C8 0.0400(7) 0.0576(8) 0.0611(8) 0.0009(7) 0.0151(6) -0.0033(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.3768(15) . ? N1 C7 1.3835(15) . ? N1 C11 1.4023(15) . ? C1 N4 1.3390(15) . ? C1 C2 1.3928(18) . ? C1 C6 1.4578(17) . ? N3 C6 1.3387(15) . ? N3 C12 1.3545(17) . ? N4 C5 1.3390(17) . ? C7 C8 1.3455(18) . ? C7 H7 0.9300 . ? C11 C12 1.3833(17) . ? C11 C10 1.4076(18) . ? C10 C9 1.354(2) . ? C10 H10 0.9300 . ? C12 C13 1.4970(16) . ? C3 C4 1.370(2) . ? C3 C2 1.380(2) . ? C3 H3 0.9300 . ? C5 C4 1.371(2) . ? C5 H5 0.9300 . ? C2 H2 0.9300 . ? C9 C8 1.416(2) . ? C9 H9 0.9300 . ? C4 H4 0.9300 . ? C13 C12 1.4970(16) 2 ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C8 H8 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C7 132.57(10) . . ? C6 N1 C11 106.57(10) . . ? C7 N1 C11 120.86(10) . . ? N4 C1 C2 122.18(12) . . ? N4 C1 C6 118.55(11) . . ? C2 C1 C6 119.27(11) . . ? C6 N3 C12 107.17(10) . . ? C1 N4 C5 117.16(12) . . ? C8 C7 N1 119.17(12) . . ? C8 C7 H7 120.4 . . ? N1 C7 H7 120.4 . . ? N3 C6 N1 110.43(10) . . ? N3 C6 C1 123.63(11) . . ? N1 C6 C1 125.92(10) . . ? C12 C11 N1 105.61(10) . . ? C12 C11 C10 135.47(12) . . ? N1 C11 C10 118.88(11) . . ? C9 C10 C11 119.76(12) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? N3 C12 C11 110.22(10) . . ? N3 C12 C13 124.10(11) . . ? C11 C12 C13 125.30(12) . . ? C4 C3 C2 118.94(14) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? N4 C5 C4 124.13(14) . . ? N4 C5 H5 117.9 . . ? C4 C5 H5 117.9 . . ? C3 C2 C1 119.10(13) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C10 C9 C8 119.93(12) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C3 C4 C5 118.49(13) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? C12 C13 C12 117.07(16) 2 . ? C12 C13 H13A 108.0 2 . ? C12 C13 H13A 108.0 . . ? C12 C13 H13B 108.0 2 . ? C12 C13 H13B 108.0 . . ? H13A C13 H13B 107.3 . . ? C7 C8 C9 121.38(13) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.180 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.036 data_ccdc_917330 _database_code_depnum_ccdc_archive 'CCDC 917330' #TrackingRef '17094_web_deposit_cif_file_0_YanmeiChen_1358858656.ccdc 917330.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C74 H50 Cu3 N18, 3(Cl2 Cu), 2(C2 H6 O)' _chemical_formula_sum 'C78 H62 Cl6 Cu6 N18 O2' _chemical_formula_weight 1877.40 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' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.8960(10) _cell_length_b 16.5030(10) _cell_length_c 27.4254(16) _cell_angle_alpha 90.00 _cell_angle_beta 101.0700(10) _cell_angle_gamma 90.00 _cell_volume 7504.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 6221 _cell_measurement_theta_min 2.438 _cell_measurement_theta_max 25.326 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3792 _exptl_absorpt_coefficient_mu 1.945 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6023 _exptl_absorpt_correction_T_max 0.6419 _exptl_absorpt_process_details 'SADABS (Bruker, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD apexII detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20149 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6548 _reflns_number_gt 5266 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX-II (Bruker, 2005)' _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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. During the refinement, the command 'omit -2 50' was used to omit the weak reflections above 50 degree. 'DFIX' and 'DANG' restraints were used for reasonable the bond distances between O1 C38, O1 C38A, C38 C39, C38A C39A, C39 O1 and C39A O1. Thermal motion of C38 c39, C38a c39a are restrained by commond 'DELU' and 'SIMU'. The ethanol molecular is dissolved as a disorder molecular, use 'part 1', 'part 2' and 'part 0' to split carbon atoms into c38 c38a c39 c39a. ; _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^)+(0.0522P)^2^+8.2587P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6548 _refine_ls_number_parameters 508 _refine_ls_number_restraints 38 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.48470(2) 0.44276(2) 0.163368(13) 0.03641(11) Uani 1 1 d . . . Cu2 Cu 0.5000 0.20307(3) 0.2500 0.04049(14) Uani 1 2 d S . . Cu3 Cu 0.0000 0.37953(4) 0.2500 0.06287(19) Uani 1 2 d S . . Cu4 Cu 0.19866(3) 0.43048(3) 0.497828(17) 0.06435(15) Uani 1 1 d . . . Cl3 Cl 0.09559(8) 0.35973(6) 0.48219(4) 0.0797(3) Uani 1 1 d . . . Cl2 Cl 0.30264(7) 0.50079(8) 0.50807(4) 0.0841(3) Uani 1 1 d . . . Cl1 Cl 0.12026(6) 0.37754(6) 0.24258(5) 0.0808(3) Uani 1 1 d . . . N5 N 0.42440(13) 0.48164(12) 0.28463(7) 0.0273(5) Uani 1 1 d . . . N9 N 0.61516(13) 0.26063(13) 0.13805(8) 0.0303(5) Uani 1 1 d . . . C24 C 0.33059(16) 0.51603(16) 0.21989(10) 0.0315(6) Uani 1 1 d . . . N6 N 0.36858(13) 0.58633(13) 0.24080(8) 0.0299(5) Uani 1 1 d . . . N2 N 0.39958(12) 0.35903(12) 0.16268(7) 0.0275(5) Uani 1 1 d . . . N7 N 0.47814(15) 0.12648(14) 0.18812(9) 0.0405(6) Uani 1 1 d . . . C12 C 0.35496(15) 0.32663(15) 0.19365(9) 0.0278(5) Uani 1 1 d . . . N8 N 0.42523(13) 0.25254(13) 0.28989(8) 0.0300(5) Uani 1 1 d . . . N3 N 0.33843(13) 0.25091(13) 0.12567(8) 0.0306(5) Uani 1 1 d . . . N1 N 0.48394(13) 0.39431(13) 0.09326(8) 0.0311(5) Uani 1 1 d . . . C13 C 0.34206(15) 0.36485(15) 0.24166(9) 0.0284(6) Uani 1 1 d . . . H13 H 0.2834 0.3659 0.2390 0.034 Uiso 1 1 calc R . . N4 N 0.52936(14) 0.56745(14) 0.34887(8) 0.0330(5) Uani 1 1 d . . . C33 C 0.6842(2) 0.2994(2) 0.07504(11) 0.0505(8) Uani 1 1 d . . . H33 H 0.6951 0.2919 0.0434 0.061 Uiso 1 1 calc R . . C25 C 0.36750(15) 0.45221(15) 0.24786(9) 0.0280(6) Uani 1 1 d . . . C1 C 0.42856(16) 0.33549(16) 0.08033(9) 0.0309(6) Uani 1 1 d . . . C36 C 0.65429(16) 0.32184(16) 0.16881(9) 0.0304(6) Uani 1 1 d . . . C19 C 0.42468(16) 0.56285(15) 0.28054(10) 0.0293(6) Uani 1 1 d . . . C37 C 0.37277(15) 0.31437(15) 0.28707(9) 0.0271(5) Uani 1 1 d . . . C11 C 0.31628(16) 0.25867(16) 0.17203(10) 0.0326(6) Uani 1 1 d . . . C21 C 0.29157(19) 0.66549(19) 0.17821(12) 0.0457(8) Uani 1 1 d . . . H21 H 0.2788 0.7154 0.1631 0.055 Uiso 1 1 calc R . . C32 C 0.62987(19) 0.25145(18) 0.09049(10) 0.0405(7) Uani 1 1 d . . . H32 H 0.6023 0.2124 0.0694 0.049 Uiso 1 1 calc R . . C20 C 0.34970(18) 0.66137(17) 0.21831(11) 0.0370(6) Uani 1 1 d . . . H20 H 0.3773 0.7078 0.2311 0.044 Uiso 1 1 calc R . . C6 C 0.38917(16) 0.31343(16) 0.12136(9) 0.0296(6) Uani 1 1 d . . . C10 C 0.26425(19) 0.20095(19) 0.18652(12) 0.0468(8) Uani 1 1 d . . . H10 H 0.2494 0.2049 0.2174 0.056 Uiso 1 1 calc R . . C7 C 0.30917(19) 0.18713(18) 0.09439(11) 0.0425(7) Uani 1 1 d . . . H7 H 0.3245 0.1817 0.0637 0.051 Uiso 1 1 calc R . . C31 C 0.56716(16) 0.21967(16) 0.16465(10) 0.0312(6) Uani 1 1 d . . . C18 C 0.57584(19) 0.60452(19) 0.38700(11) 0.0431(7) Uani 1 1 d . . . H18 H 0.6135 0.5737 0.4084 0.052 Uiso 1 1 calc R . . C15 C 0.46717(19) 0.69515(18) 0.32564(12) 0.0435(7) Uani 1 1 d . . . H15 H 0.4289 0.7253 0.3042 0.052 Uiso 1 1 calc R . . C5 C 0.52266(17) 0.42185(18) 0.05850(11) 0.0383(7) Uani 1 1 d . . . H5 H 0.5604 0.4629 0.0671 0.046 Uiso 1 1 calc R . . C34 C 0.7253(2) 0.3608(2) 0.10569(12) 0.0520(8) Uani 1 1 d . . . H34 H 0.7630 0.3931 0.0943 0.062 Uiso 1 1 calc R . . C8 C 0.2587(2) 0.1336(2) 0.10864(13) 0.0538(9) Uani 1 1 d . . . H8 H 0.2383 0.0915 0.0873 0.065 Uiso 1 1 calc R . . C14 C 0.47499(16) 0.61274(16) 0.31825(10) 0.0305(6) Uani 1 1 d . . . C35 C 0.70975(18) 0.37250(18) 0.15149(11) 0.0402(7) Uani 1 1 d . . . H35 H 0.7355 0.4138 0.1715 0.048 Uiso 1 1 calc R . . C23 C 0.26865(19) 0.52256(19) 0.17826(11) 0.0459(7) Uani 1 1 d . . . H23 H 0.2413 0.4765 0.1646 0.055 Uiso 1 1 calc R . . C9 C 0.2358(2) 0.1396(2) 0.15533(14) 0.0572(9) Uani 1 1 d . . . H9 H 0.2012 0.1013 0.1647 0.069 Uiso 1 1 calc R . . C30 C 0.4360(2) 0.0575(2) 0.18318(14) 0.0538(8) Uani 1 1 d . . . H30 H 0.4087 0.0427 0.2082 0.065 Uiso 1 1 calc R . . C2 C 0.4117(2) 0.3048(2) 0.03265(11) 0.0463(8) Uani 1 1 d . . . H2 H 0.3723 0.2652 0.0240 0.056 Uiso 1 1 calc R . . C28 C 0.4689(2) 0.0297(2) 0.10577(16) 0.0701(11) Uani 1 1 d . . . H28 H 0.4646 -0.0026 0.0776 0.084 Uiso 1 1 calc R . . C17 C 0.5711(2) 0.6859(2) 0.39631(12) 0.0521(8) Uani 1 1 d . . . H17 H 0.6046 0.7093 0.4236 0.063 Uiso 1 1 calc R . . C29 C 0.4315(2) 0.0079(2) 0.14301(16) 0.0642(10) Uani 1 1 d . . . H29 H 0.4029 -0.0405 0.1413 0.077 Uiso 1 1 calc R . . C4 C 0.5098(2) 0.3930(2) 0.01108(11) 0.0474(8) Uani 1 1 d . . . H4 H 0.5386 0.4134 -0.0119 0.057 Uiso 1 1 calc R . . C22 C 0.2486(2) 0.5958(2) 0.15798(12) 0.0542(9) Uani 1 1 d . . . H22 H 0.2067 0.6006 0.1307 0.065 Uiso 1 1 calc R . . C27 C 0.5138(2) 0.1003(2) 0.10965(14) 0.0558(9) Uani 1 1 d . . . H27 H 0.5404 0.1158 0.0844 0.067 Uiso 1 1 calc R . . C16 C 0.5168(2) 0.7317(2) 0.36506(13) 0.0516(8) Uani 1 1 d . . . H16 H 0.5133 0.7872 0.3703 0.062 Uiso 1 1 calc R . . C26 C 0.51840(17) 0.14751(17) 0.15192(11) 0.0364(6) Uani 1 1 d . . . C3 C 0.4538(2) 0.3336(2) -0.00176(12) 0.0539(9) Uani 1 1 d . . . H3 H 0.4441 0.3126 -0.0338 0.065 Uiso 1 1 calc R . . O1 O 0.3017(3) 0.1541(2) -0.02586(15) 0.1289(15) Uani 1 1 d D . . H1 H 0.2628 0.1221 -0.0244 0.193 Uiso 1 1 d R A . C38 C 0.3673(5) 0.1176(7) -0.0445(3) 0.147(3) Uani 0.570(8) 1 d PDU A 1 H38A H 0.3644 0.0591 -0.0424 0.176 Uiso 0.570(8) 1 calc PR A 1 H38B H 0.4185 0.1353 -0.0250 0.176 Uiso 0.570(8) 1 calc PR A 1 C39 C 0.3607(7) 0.1429(8) -0.0969(3) 0.147(3) Uani 0.570(8) 1 d PDU A 1 H39A H 0.3093 0.1265 -0.1157 0.220 Uiso 0.570(8) 1 calc PR A 1 H39B H 0.4030 0.1179 -0.1105 0.220 Uiso 0.570(8) 1 calc PR A 1 H39C H 0.3656 0.2008 -0.0984 0.220 Uiso 0.570(8) 1 calc PR A 1 C38A C 0.3176(9) 0.1441(9) -0.0752(2) 0.146(3) Uiso 0.430(8) 1 d PDU A 2 H38C H 0.3371 0.1945 -0.0868 0.176 Uiso 0.430(8) 1 calc PR A 2 H38D H 0.2686 0.1286 -0.0979 0.176 Uiso 0.430(8) 1 calc PR A 2 C39A C 0.3793(9) 0.0799(9) -0.0733(5) 0.147(3) Uiso 0.430(8) 1 d PDU A 2 H39D H 0.4123 0.0782 -0.0407 0.220 Uiso 0.430(8) 1 calc PR A 2 H39E H 0.4124 0.0915 -0.0973 0.220 Uiso 0.430(8) 1 calc PR A 2 H39F H 0.3532 0.0285 -0.0808 0.220 Uiso 0.430(8) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0398(2) 0.0339(2) 0.03384(19) -0.00542(14) 0.00292(15) -0.00862(15) Cu2 0.0458(3) 0.0430(3) 0.0360(3) 0.000 0.0162(2) 0.000 Cu3 0.0477(3) 0.0507(4) 0.0871(5) 0.000 0.0051(3) 0.000 Cu4 0.0814(3) 0.0633(3) 0.0474(3) 0.0023(2) 0.0100(2) 0.0101(2) Cl3 0.1122(9) 0.0661(6) 0.0557(6) 0.0153(5) 0.0037(6) -0.0111(6) Cl2 0.0718(7) 0.0909(8) 0.0832(8) 0.0091(6) -0.0012(6) 0.0098(6) Cl1 0.0508(5) 0.0641(6) 0.1268(10) -0.0193(6) 0.0149(6) -0.0007(5) N5 0.0313(12) 0.0262(11) 0.0251(11) 0.0015(9) 0.0070(9) 0.0027(9) N9 0.0362(12) 0.0305(12) 0.0239(11) -0.0009(9) 0.0050(9) 0.0072(10) C24 0.0339(14) 0.0320(14) 0.0283(14) 0.0009(11) 0.0050(12) 0.0046(12) N6 0.0344(12) 0.0267(11) 0.0294(12) 0.0021(9) 0.0084(10) 0.0063(9) N2 0.0297(11) 0.0293(11) 0.0232(11) -0.0002(9) 0.0043(9) -0.0029(9) N7 0.0404(14) 0.0340(13) 0.0455(15) -0.0037(11) 0.0043(12) -0.0040(11) C12 0.0292(13) 0.0292(13) 0.0243(13) 0.0022(10) 0.0031(11) 0.0002(11) N8 0.0331(12) 0.0291(12) 0.0286(12) 0.0028(9) 0.0083(9) -0.0025(10) N3 0.0336(12) 0.0329(12) 0.0256(11) -0.0032(9) 0.0059(9) -0.0061(10) N1 0.0334(12) 0.0323(12) 0.0280(12) 0.0010(9) 0.0072(10) -0.0009(10) C13 0.0284(13) 0.0317(14) 0.0248(13) -0.0002(11) 0.0045(11) 0.0001(11) N4 0.0360(12) 0.0349(13) 0.0286(12) -0.0003(9) 0.0074(10) -0.0049(10) C33 0.070(2) 0.059(2) 0.0274(15) 0.0036(14) 0.0207(15) 0.0082(17) C25 0.0315(14) 0.0290(14) 0.0239(13) 0.0006(10) 0.0063(11) 0.0027(11) C1 0.0358(15) 0.0313(14) 0.0253(13) -0.0004(11) 0.0054(11) 0.0019(12) C36 0.0358(15) 0.0288(14) 0.0262(13) 0.0012(11) 0.0051(11) 0.0059(11) C19 0.0312(14) 0.0281(14) 0.0297(14) 0.0020(11) 0.0091(11) 0.0056(11) C37 0.0307(13) 0.0251(13) 0.0251(13) -0.0004(10) 0.0042(11) -0.0035(11) C11 0.0346(15) 0.0353(15) 0.0286(14) -0.0031(11) 0.0080(12) -0.0038(12) C21 0.0531(19) 0.0382(17) 0.0450(18) 0.0116(14) 0.0077(15) 0.0178(15) C32 0.0537(18) 0.0423(17) 0.0254(14) -0.0021(12) 0.0074(13) 0.0081(14) C20 0.0457(17) 0.0289(14) 0.0390(16) 0.0050(12) 0.0149(14) 0.0105(12) C6 0.0335(14) 0.0307(14) 0.0235(13) -0.0008(11) 0.0025(11) -0.0025(11) C10 0.0517(19) 0.0475(18) 0.0459(18) -0.0045(14) 0.0215(15) -0.0161(15) C7 0.0488(18) 0.0435(17) 0.0345(15) -0.0130(13) 0.0060(13) -0.0105(14) C31 0.0350(15) 0.0310(14) 0.0275(14) -0.0020(11) 0.0060(11) 0.0027(11) C18 0.0443(17) 0.0493(19) 0.0343(16) 0.0011(13) 0.0039(14) -0.0048(14) C15 0.0501(18) 0.0326(16) 0.0471(18) -0.0017(13) 0.0075(15) 0.0017(13) C5 0.0385(16) 0.0399(16) 0.0372(16) 0.0057(13) 0.0093(13) -0.0023(13) C34 0.062(2) 0.059(2) 0.0400(18) 0.0099(15) 0.0208(16) -0.0051(17) C8 0.063(2) 0.0474(19) 0.053(2) -0.0176(16) 0.0167(17) -0.0216(17) C14 0.0333(14) 0.0307(14) 0.0289(14) 0.0009(11) 0.0097(11) -0.0008(11) C35 0.0489(17) 0.0383(16) 0.0342(15) 0.0055(12) 0.0099(13) -0.0019(13) C23 0.0475(18) 0.0425(18) 0.0420(17) 0.0004(14) -0.0055(14) 0.0056(14) C9 0.060(2) 0.054(2) 0.063(2) -0.0130(17) 0.0250(18) -0.0278(17) C30 0.053(2) 0.0442(19) 0.063(2) -0.0031(16) 0.0104(17) -0.0106(16) C2 0.059(2) 0.0498(18) 0.0312(16) -0.0066(13) 0.0121(14) -0.0147(16) C28 0.072(3) 0.063(2) 0.073(3) -0.038(2) 0.008(2) -0.015(2) C17 0.058(2) 0.056(2) 0.0414(18) -0.0139(15) 0.0056(16) -0.0158(17) C29 0.062(2) 0.047(2) 0.080(3) -0.0156(19) 0.006(2) -0.0175(17) C4 0.059(2) 0.053(2) 0.0347(17) 0.0097(14) 0.0207(15) 0.0011(16) C22 0.057(2) 0.056(2) 0.0429(18) 0.0068(15) -0.0097(16) 0.0171(17) C27 0.056(2) 0.060(2) 0.053(2) -0.0238(17) 0.0138(17) -0.0100(17) C16 0.066(2) 0.0351(17) 0.055(2) -0.0120(15) 0.0147(17) -0.0096(16) C26 0.0346(15) 0.0368(16) 0.0368(15) -0.0054(12) 0.0047(13) 0.0036(12) C3 0.072(2) 0.063(2) 0.0295(16) -0.0071(15) 0.0178(16) -0.0101(18) O1 0.155(4) 0.124(3) 0.122(3) -0.048(3) 0.063(3) -0.051(3) C38 0.147(3) 0.147(3) 0.147(3) -0.0003(8) 0.0287(10) 0.0001(8) C39 0.147(3) 0.147(3) 0.147(3) -0.0001(7) 0.0282(8) 0.0001(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 Cu1 N5 1.991(2) 2_655 ? Cu1 N2 1.992(2) . ? Cu1 N1 2.080(2) . ? Cu1 N4 2.091(2) 2_655 ? Cu2 N8 1.998(2) 2_655 ? Cu2 N8 1.998(2) . ? Cu2 N7 2.091(2) . ? Cu2 N7 2.091(2) 2_655 ? Cu3 Cl1 2.0809(10) 2 ? Cu3 Cl1 2.0809(10) . ? Cu4 Cl3 2.0720(13) . ? Cu4 Cl2 2.0790(14) . ? N5 C19 1.345(3) . ? N5 C25 1.343(3) . ? N5 Cu1 1.991(2) 2_655 ? N9 C31 1.369(3) . ? N9 C32 1.382(3) . ? N9 C36 1.398(3) . ? C24 C25 1.379(4) . ? C24 N6 1.395(3) . ? C24 C23 1.397(4) . ? N6 C19 1.356(3) . ? N6 C20 1.393(3) . ? N2 C6 1.343(3) . ? N2 C12 1.350(3) . ? N7 C30 1.336(4) . ? N7 C26 1.352(4) . ? C12 C11 1.374(4) . ? C12 C13 1.513(4) . ? N8 C31 1.343(3) 2_655 ? N8 C37 1.344(3) . ? N3 C6 1.361(3) . ? N3 C7 1.388(3) . ? N3 C11 1.399(3) . ? N1 C5 1.335(4) . ? N1 C1 1.348(3) . ? C13 C37 1.505(3) . ? C13 C25 1.505(4) . ? C13 H13 0.9800 . ? N4 C18 1.330(4) . ? N4 C14 1.346(3) . ? N4 Cu1 2.091(2) 2_655 ? C33 C32 1.341(5) . ? C33 C34 1.411(5) . ? C33 H33 0.9300 . ? C1 C2 1.380(4) . ? C1 C6 1.459(4) . ? C36 C37 1.379(4) 2_655 ? C36 C35 1.405(4) . ? C19 C14 1.460(4) . ? C37 C36 1.379(4) 2_655 ? C11 C10 1.404(4) . ? C21 C20 1.328(4) . ? C21 C22 1.415(5) . ? C21 H21 0.9300 . ? C32 H32 0.9300 . ? C20 H20 0.9300 . ? C10 C9 1.353(5) . ? C10 H10 0.9300 . ? C7 C8 1.337(4) . ? C7 H7 0.9300 . ? C31 N8 1.343(3) 2_655 ? C31 C26 1.452(4) . ? C18 C17 1.372(5) . ? C18 H18 0.9300 . ? C15 C16 1.374(4) . ? C15 C14 1.385(4) . ? C15 H15 0.9300 . ? C5 C4 1.362(4) . ? C5 H5 0.9300 . ? C34 C35 1.346(4) . ? C34 H34 0.9300 . ? C8 C9 1.411(5) . ? C8 H8 0.9300 . ? C35 H35 0.9300 . ? C23 C22 1.346(4) . ? C23 H23 0.9300 . ? C9 H9 0.9300 . ? C30 C29 1.363(5) . ? C30 H30 0.9300 . ? C2 C3 1.372(4) . ? C2 H2 0.9300 . ? C28 C29 1.350(6) . ? C28 C27 1.383(5) . ? C28 H28 0.9300 . ? C17 C16 1.360(5) . ? C17 H17 0.9300 . ? C29 H29 0.9300 . ? C4 C3 1.361(5) . ? C4 H4 0.9300 . ? C22 H22 0.9300 . ? C27 C26 1.386(4) . ? C27 H27 0.9300 . ? C16 H16 0.9300 . ? C3 H3 0.9300 . ? O1 C38A 1.4395(10) . ? O1 C38 1.4397(10) . ? O1 H1 0.8500 . ? C38 C39 1.4796(10) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C38A C39A 1.4794(10) . ? C38A H38C 0.9700 . ? C38A H38D 0.9700 . ? C39A H39D 0.9600 . ? C39A H39E 0.9600 . ? C39A H39F 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 N5 Cu1 N2 133.36(8) 2_655 . ? N5 Cu1 N1 130.77(9) 2_655 . ? N2 Cu1 N1 81.28(8) . . ? N5 Cu1 N4 81.15(9) 2_655 2_655 ? N2 Cu1 N4 128.43(9) . 2_655 ? N1 Cu1 N4 104.45(9) . 2_655 ? N8 Cu2 N8 131.75(12) 2_655 . ? N8 Cu2 N7 80.46(9) 2_655 . ? N8 Cu2 N7 131.28(9) . . ? N8 Cu2 N7 131.28(9) 2_655 2_655 ? N8 Cu2 N7 80.46(9) . 2_655 ? N7 Cu2 N7 105.63(14) . 2_655 ? Cl1 Cu3 Cl1 178.19(7) 2 . ? Cl3 Cu4 Cl2 175.80(5) . . ? C19 N5 C25 108.1(2) . . ? C19 N5 Cu1 111.49(17) . 2_655 ? C25 N5 Cu1 139.80(18) . 2_655 ? C31 N9 C32 132.9(2) . . ? C31 N9 C36 107.2(2) . . ? C32 N9 C36 119.9(2) . . ? C25 C24 N6 106.5(2) . . ? C25 C24 C23 134.5(3) . . ? N6 C24 C23 119.0(2) . . ? C19 N6 C24 106.7(2) . . ? C19 N6 C20 132.5(2) . . ? C24 N6 C20 120.6(2) . . ? C6 N2 C12 108.1(2) . . ? C6 N2 Cu1 111.96(17) . . ? C12 N2 Cu1 139.32(17) . . ? C30 N7 C26 118.5(3) . . ? C30 N7 Cu2 127.2(2) . . ? C26 N7 Cu2 113.92(18) . . ? N2 C12 C11 109.2(2) . . ? N2 C12 C13 125.0(2) . . ? C11 C12 C13 125.4(2) . . ? C31 N8 C37 107.7(2) 2_655 . ? C31 N8 Cu2 112.67(18) 2_655 . ? C37 N8 Cu2 139.31(17) . . ? C6 N3 C7 132.6(2) . . ? C6 N3 C11 107.0(2) . . ? C7 N3 C11 120.4(2) . . ? C5 N1 C1 117.9(2) . . ? C5 N1 Cu1 127.75(19) . . ? C1 N1 Cu1 113.62(17) . . ? C37 C13 C25 113.0(2) . . ? C37 C13 C12 113.9(2) . . ? C25 C13 C12 114.3(2) . . ? C37 C13 H13 104.8 . . ? C25 C13 H13 104.8 . . ? C12 C13 H13 104.8 . . ? C18 N4 C14 117.7(2) . . ? C18 N4 Cu1 127.6(2) . 2_655 ? C14 N4 Cu1 113.79(17) . 2_655 ? C32 C33 C34 121.6(3) . . ? C32 C33 H33 119.2 . . ? C34 C33 H33 119.2 . . ? N5 C25 C24 108.9(2) . . ? N5 C25 C13 125.4(2) . . ? C24 C25 C13 125.4(2) . . ? N1 C1 C2 121.3(3) . . ? N1 C1 C6 111.9(2) . . ? C2 C1 C6 126.7(3) . . ? C37 C36 N9 105.5(2) 2_655 . ? C37 C36 C35 134.8(3) 2_655 . ? N9 C36 C35 119.6(2) . . ? N5 C19 N6 109.8(2) . . ? N5 C19 C14 120.9(2) . . ? N6 C19 C14 129.0(2) . . ? N8 C37 C36 110.1(2) . 2_655 ? N8 C37 C13 125.9(2) . . ? C36 C37 C13 123.8(2) 2_655 . ? C12 C11 N3 106.2(2) . . ? C12 C11 C10 134.7(3) . . ? N3 C11 C10 119.1(2) . . ? C20 C21 C22 121.7(3) . . ? C20 C21 H21 119.2 . . ? C22 C21 H21 119.2 . . ? C33 C32 N9 119.5(3) . . ? C33 C32 H32 120.3 . . ? N9 C32 H32 120.3 . . ? C21 C20 N6 118.8(3) . . ? C21 C20 H20 120.6 . . ? N6 C20 H20 120.6 . . ? N2 C6 N3 109.5(2) . . ? N2 C6 C1 120.4(2) . . ? N3 C6 C1 130.1(2) . . ? C9 C10 C11 119.6(3) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C8 C7 N3 119.5(3) . . ? C8 C7 H7 120.3 . . ? N3 C7 H7 120.3 . . ? N8 C31 N9 109.5(2) 2_655 . ? N8 C31 C26 120.2(2) 2_655 . ? N9 C31 C26 130.1(2) . . ? N4 C18 C17 123.3(3) . . ? N4 C18 H18 118.3 . . ? C17 C18 H18 118.3 . . ? C16 C15 C14 119.1(3) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? N1 C5 C4 123.6(3) . . ? N1 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? C35 C34 C33 119.9(3) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? C7 C8 C9 121.4(3) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? N4 C14 C15 121.8(3) . . ? N4 C14 C19 111.3(2) . . ? C15 C14 C19 126.8(3) . . ? C34 C35 C36 119.5(3) . . ? C34 C35 H35 120.2 . . ? C36 C35 H35 120.2 . . ? C22 C23 C24 119.7(3) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? N7 C30 C29 122.7(4) . . ? N7 C30 H30 118.6 . . ? C29 C30 H30 118.6 . . ? C3 C2 C1 119.0(3) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C29 C28 C27 119.8(3) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C16 C17 C18 119.0(3) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C28 C29 C30 119.3(3) . . ? C28 C29 H29 120.4 . . ? C30 C29 H29 120.4 . . ? C5 C4 C3 118.3(3) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? C23 C22 C21 119.9(3) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C28 C27 C26 118.6(3) . . ? C28 C27 H27 120.7 . . ? C26 C27 H27 120.7 . . ? C17 C16 C15 119.2(3) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? N7 C26 C27 121.0(3) . . ? N7 C26 C31 112.1(2) . . ? C27 C26 C31 126.9(3) . . ? C4 C3 C2 119.9(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C38A O1 C38 47.3(5) . . ? C38A O1 H1 104.9 . . ? C38 O1 H1 114.3 . . ? O1 C38 C39 107.86(10) . . ? O1 C38 H38A 110.1 . . ? C39 C38 H38A 110.1 . . ? O1 C38 H38B 110.1 . . ? C39 C38 H38B 110.1 . . ? H38A C38 H38B 108.4 . . ? O1 C38A C39A 107.90(11) . . ? O1 C38A H38C 110.1 . . ? C39A C38A H38C 110.1 . . ? O1 C38A H38D 110.1 . . ? C39A C38A H38D 110.1 . . ? H38C C38A H38D 108.4 . . ? C38A C39A H39D 109.5 . . ? C38A C39A H39E 109.5 . . ? H39D C39A H39E 109.5 . . ? C38A C39A H39F 109.5 . . ? H39D C39A H39F 109.5 . . ? H39E C39A H39F 109.5 . . ? 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 C25 C24 N6 C19 -1.3(3) . . . . ? C23 C24 N6 C19 179.2(3) . . . . ? C25 C24 N6 C20 174.4(2) . . . . ? C23 C24 N6 C20 -5.1(4) . . . . ? N5 Cu1 N2 C6 -136.13(17) 2_655 . . . ? N1 Cu1 N2 C6 3.67(17) . . . . ? N4 Cu1 N2 C6 105.24(19) 2_655 . . . ? N5 Cu1 N2 C12 33.2(3) 2_655 . . . ? N1 Cu1 N2 C12 173.0(3) . . . . ? N4 Cu1 N2 C12 -85.5(3) 2_655 . . . ? N8 Cu2 N7 C30 170.2(3) 2_655 . . . ? N8 Cu2 N7 C30 -51.1(3) . . . . ? N7 Cu2 N7 C30 39.9(2) 2_655 . . . ? N8 Cu2 N7 C26 -3.18(19) 2_655 . . . ? N8 Cu2 N7 C26 135.50(19) . . . . ? N7 Cu2 N7 C26 -133.5(2) 2_655 . . . ? C6 N2 C12 C11 0.8(3) . . . . ? Cu1 N2 C12 C11 -168.8(2) . . . . ? C6 N2 C12 C13 -172.6(2) . . . . ? Cu1 N2 C12 C13 17.9(4) . . . . ? N8 Cu2 N8 C31 -131.82(19) 2_655 . . 2_655 ? N7 Cu2 N8 C31 108.97(19) . . . 2_655 ? N7 Cu2 N8 C31 6.49(18) 2_655 . . 2_655 ? N8 Cu2 N8 C37 41.0(2) 2_655 . . . ? N7 Cu2 N8 C37 -78.2(3) . . . . ? N7 Cu2 N8 C37 179.3(3) 2_655 . . . ? N5 Cu1 N1 C5 -46.2(3) 2_655 . . . ? N2 Cu1 N1 C5 172.1(2) . . . . ? N4 Cu1 N1 C5 44.5(2) 2_655 . . . ? N5 Cu1 N1 C1 143.82(17) 2_655 . . . ? N2 Cu1 N1 C1 2.10(18) . . . . ? N4 Cu1 N1 C1 -125.48(18) 2_655 . . . ? N2 C12 C13 C37 -118.9(3) . . . . ? C11 C12 C13 C37 68.8(3) . . . . ? N2 C12 C13 C25 13.1(4) . . . . ? C11 C12 C13 C25 -159.2(3) . . . . ? C19 N5 C25 C24 -0.2(3) . . . . ? Cu1 N5 C25 C24 -170.0(2) 2_655 . . . ? C19 N5 C25 C13 -174.0(2) . . . . ? Cu1 N5 C25 C13 16.1(4) 2_655 . . . ? N6 C24 C25 N5 1.0(3) . . . . ? C23 C24 C25 N5 -179.6(3) . . . . ? N6 C24 C25 C13 174.8(2) . . . . ? C23 C24 C25 C13 -5.8(5) . . . . ? C37 C13 C25 N5 13.2(4) . . . . ? C12 C13 C25 N5 -119.3(3) . . . . ? C37 C13 C25 C24 -159.6(2) . . . . ? C12 C13 C25 C24 67.9(3) . . . . ? C5 N1 C1 C2 -0.5(4) . . . . ? Cu1 N1 C1 C2 170.6(2) . . . . ? C5 N1 C1 C6 -178.0(2) . . . . ? Cu1 N1 C1 C6 -6.9(3) . . . . ? C31 N9 C36 C37 -0.1(3) . . . 2_655 ? C32 N9 C36 C37 -179.7(2) . . . 2_655 ? C31 N9 C36 C35 178.2(2) . . . . ? C32 N9 C36 C35 -1.4(4) . . . . ? C25 N5 C19 N6 -0.7(3) . . . . ? Cu1 N5 C19 N6 172.30(16) 2_655 . . . ? C25 N5 C19 C14 174.0(2) . . . . ? Cu1 N5 C19 C14 -13.0(3) 2_655 . . . ? C24 N6 C19 N5 1.2(3) . . . . ? C20 N6 C19 N5 -173.8(3) . . . . ? C24 N6 C19 C14 -172.9(3) . . . . ? C20 N6 C19 C14 12.1(5) . . . . ? C31 N8 C37 C36 -0.1(3) 2_655 . . 2_655 ? Cu2 N8 C37 C36 -173.1(2) . . . 2_655 ? C31 N8 C37 C13 -175.7(2) 2_655 . . . ? Cu2 N8 C37 C13 11.3(4) . . . . ? C25 C13 C37 N8 -115.5(3) . . . . ? C12 C13 C37 N8 17.2(4) . . . . ? C25 C13 C37 C36 69.6(3) . . . 2_655 ? C12 C13 C37 C36 -157.8(2) . . . 2_655 ? N2 C12 C11 N3 -0.7(3) . . . . ? C13 C12 C11 N3 172.7(2) . . . . ? N2 C12 C11 C10 178.9(3) . . . . ? C13 C12 C11 C10 -7.8(5) . . . . ? C6 N3 C11 C12 0.3(3) . . . . ? C7 N3 C11 C12 179.8(2) . . . . ? C6 N3 C11 C10 -179.3(3) . . . . ? C7 N3 C11 C10 0.2(4) . . . . ? C34 C33 C32 N9 -1.9(5) . . . . ? C31 N9 C32 C33 -176.7(3) . . . . ? C36 N9 C32 C33 2.8(4) . . . . ? C22 C21 C20 N6 0.0(5) . . . . ? C19 N6 C20 C21 178.3(3) . . . . ? C24 N6 C20 C21 3.9(4) . . . . ? C12 N2 C6 N3 -0.6(3) . . . . ? Cu1 N2 C6 N3 172.08(16) . . . . ? C12 N2 C6 C1 178.2(2) . . . . ? Cu1 N2 C6 C1 -9.1(3) . . . . ? C7 N3 C6 N2 -179.2(3) . . . . ? C11 N3 C6 N2 0.2(3) . . . . ? C7 N3 C6 C1 2.1(5) . . . . ? C11 N3 C6 C1 -178.5(3) . . . . ? N1 C1 C6 N2 10.9(3) . . . . ? C2 C1 C6 N2 -166.4(3) . . . . ? N1 C1 C6 N3 -170.5(3) . . . . ? C2 C1 C6 N3 12.1(5) . . . . ? C12 C11 C10 C9 179.8(3) . . . . ? N3 C11 C10 C9 -0.7(5) . . . . ? C6 N3 C7 C8 -179.8(3) . . . . ? C11 N3 C7 C8 0.8(4) . . . . ? C32 N9 C31 N8 179.5(3) . . . 2_655 ? C36 N9 C31 N8 0.0(3) . . . 2_655 ? C32 N9 C31 C26 4.6(5) . . . . ? C36 N9 C31 C26 -175.0(3) . . . . ? C14 N4 C18 C17 -0.2(4) . . . . ? Cu1 N4 C18 C17 -168.6(2) 2_655 . . . ? C1 N1 C5 C4 -0.8(4) . . . . ? Cu1 N1 C5 C4 -170.4(2) . . . . ? C32 C33 C34 C35 -0.4(5) . . . . ? N3 C7 C8 C9 -1.3(5) . . . . ? C18 N4 C14 C15 0.2(4) . . . . ? Cu1 N4 C14 C15 170.1(2) 2_655 . . . ? C18 N4 C14 C19 -175.8(2) . . . . ? Cu1 N4 C14 C19 -5.9(3) 2_655 . . . ? C16 C15 C14 N4 0.6(4) . . . . ? C16 C15 C14 C19 175.9(3) . . . . ? N5 C19 C14 N4 12.9(3) . . . . ? N6 C19 C14 N4 -173.6(2) . . . . ? N5 C19 C14 C15 -162.9(3) . . . . ? N6 C19 C14 C15 10.7(5) . . . . ? C33 C34 C35 C36 1.7(5) . . . . ? C37 C36 C35 C34 176.8(3) 2_655 . . . ? N9 C36 C35 C34 -0.8(4) . . . . ? C25 C24 C23 C22 -176.9(3) . . . . ? N6 C24 C23 C22 2.4(4) . . . . ? C11 C10 C9 C8 0.3(6) . . . . ? C7 C8 C9 C10 0.8(6) . . . . ? C26 N7 C30 C29 -0.6(5) . . . . ? Cu2 N7 C30 C29 -173.7(3) . . . . ? N1 C1 C2 C3 1.7(5) . . . . ? C6 C1 C2 C3 178.8(3) . . . . ? N4 C18 C17 C16 -0.5(5) . . . . ? C27 C28 C29 C30 2.4(6) . . . . ? N7 C30 C29 C28 -1.9(6) . . . . ? N1 C5 C4 C3 0.8(5) . . . . ? C24 C23 C22 C21 1.4(5) . . . . ? C20 C21 C22 C23 -2.7(5) . . . . ? C29 C28 C27 C26 -0.6(6) . . . . ? C18 C17 C16 C15 1.2(5) . . . . ? C14 C15 C16 C17 -1.3(5) . . . . ? C30 N7 C26 C27 2.4(4) . . . . ? Cu2 N7 C26 C27 176.4(2) . . . . ? C30 N7 C26 C31 -174.6(3) . . . . ? Cu2 N7 C26 C31 -0.6(3) . . . . ? C28 C27 C26 N7 -1.8(5) . . . . ? C28 C27 C26 C31 174.7(3) . . . . ? N8 C31 C26 N7 6.6(4) 2_655 . . . ? N9 C31 C26 N7 -178.9(3) . . . . ? N8 C31 C26 C27 -170.2(3) 2_655 . . . ? N9 C31 C26 C27 4.3(5) . . . . ? C5 C4 C3 C2 0.4(5) . . . . ? C1 C2 C3 C4 -1.6(5) . . . . ? C38A O1 C38 C39 13.8(12) . . . . ? C38 O1 C38A C39A 18.2(12) . . . . ? 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 O1 H1 Cl2 0.85 2.37 3.175(4) 157.9 4_545 C2 H2 O1 0.93 2.45 3.327(5) 156.1 . C7 H7 O1 0.93 2.46 3.321(5) 154.8 . C13 H13 Cl1 0.98 2.78 3.758(3) 173.1 . C18 H18 Cl2 0.93 2.74 3.640(3) 162.6 5_666 C32 H32 Cl3 0.93 2.65 3.444(3) 143.3 8 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.458 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.060