Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Hideo Takagi' 'Sumitaka Itoh' 'Nobuyuki Kishikawa' 'Takayoshi Suzuki' _publ_contact_author_name 'Dr Hideo Takagi' _publ_contact_author_address ; Department of Chemistry Nagoya University Furo-cho Chikusa Nagoya Aichi 464-8602 JAPAN ; _publ_contact_author_email HTAKAGI@CHEM.NAGOYA-U.AC.JP _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Syntheses, Structural Analyses, and Redox Kinetics of Four-coordinate [CuL2]2+ and Five-coordinate [CuL2(solvent)]2+ Complexes (L = 6,6'-dimethyl-2,2'-bipyridine or 2,9-dimethyl-1,10-phenanthroline): Completely Gated Reduction Reaction of [Cu(dmp)2]2+ in Nitromethane ; data_CudmbpH2O _database_code_depnum_ccdc_archive 'CCDC 251495' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Aquobis(6,6'-dimethyl-2,2'-bipyridine)copper(II) perchlorate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H26 Cu N4 O 2+, 2(Cl O4 1-)' _chemical_formula_sum 'C24 H26 Cl2 Cu N4 O9' _chemical_formula_weight 648.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 14.007(6) _cell_length_b 10.951(5) _cell_length_c 18.099(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.57(3) _cell_angle_gamma 90.00 _cell_volume 2720.0(18) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 12348 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1332 _exptl_absorpt_coefficient_mu 1.061 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.809 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis-rapid' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21731 _diffrn_reflns_av_R_equivalents 0.0865 _diffrn_reflns_av_sigmaI/netI 0.0798 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5915 _reflns_number_gt 3928 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'teXsan ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ORTEP _computing_publication_material SHELXL-97 _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^)+(0.0670P)^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 5915 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1389 _refine_ls_wR_factor_gt 0.1321 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 0.35505(3) 0.02793(4) 0.23844(2) 0.02414(13) Uani 1 1 d . . . Cl1 Cl 0.31646(8) -0.36903(11) 0.37160(6) 0.0407(3) Uani 1 1 d . . . Cl2 Cl 0.36332(7) -0.30014(9) 0.05793(5) 0.0343(2) Uani 1 1 d . . . O1 O 0.3049(2) -0.1487(3) 0.22388(16) 0.0361(6) Uani 1 1 d . . . O11 O 0.2962(4) -0.2420(4) 0.3659(2) 0.0892(15) Uani 1 1 d . . . O12 O 0.3952(4) -0.3910(5) 0.4307(2) 0.0962(16) Uani 1 1 d . . . O13 O 0.3382(3) -0.4094(4) 0.3022(2) 0.0717(12) Uani 1 1 d . . . O14 O 0.2349(3) -0.4336(5) 0.3847(3) 0.0989(17) Uani 1 1 d . . . O21 O 0.3619(3) -0.1733(3) 0.0440(2) 0.0655(11) Uani 1 1 d . . . O22 O 0.4517(3) -0.3515(4) 0.0447(2) 0.0716(11) Uani 1 1 d . . . O23 O 0.3600(3) -0.3228(3) 0.13572(17) 0.0581(10) Uani 1 1 d . . . O24 O 0.2838(2) -0.3596(3) 0.01152(19) 0.0548(9) Uani 1 1 d . . . N1 N 0.2291(2) 0.0465(3) 0.27201(19) 0.0334(8) Uani 1 1 d . . . N2 N 0.4068(3) 0.0890(3) 0.35161(18) 0.0378(8) Uani 1 1 d . . . N3 N 0.3634(2) 0.1807(3) 0.17392(16) 0.0264(6) Uani 1 1 d . . . N4 N 0.4700(2) -0.0186(3) 0.19696(16) 0.0264(6) Uani 1 1 d . . . C1 C 0.1379(4) 0.0201(5) 0.1441(3) 0.0568(13) Uani 1 1 d . . . H1A H 0.1598 0.0982 0.1269 0.069 Uiso 1 1 calc R . . H1B H 0.0708 0.0041 0.1179 0.069 Uiso 1 1 calc R . . H1C H 0.1804 -0.0456 0.1329 0.069 Uiso 1 1 calc R . . C2 C 0.1421(3) 0.0254(4) 0.2267(3) 0.0448(10) Uani 1 1 d . . . C3 C 0.0609(4) 0.0101(5) 0.2576(4) 0.0706(18) Uani 1 1 d . . . H3 H -0.0011 -0.0030 0.2260 0.084 Uiso 1 1 calc R . . C4 C 0.0698(5) 0.0137(5) 0.3349(5) 0.082(2) Uani 1 1 d . . . H4 H 0.0144 -0.0005 0.3566 0.100 Uiso 1 1 calc R . . C5 C 0.1561(6) 0.0372(5) 0.3794(4) 0.075(2) Uani 1 1 d . . . H5 H 0.1621 0.0416 0.4325 0.091 Uiso 1 1 calc R . . C6 C 0.2372(4) 0.0552(4) 0.3470(3) 0.0440(12) Uani 1 1 d . . . C7 C 0.3340(4) 0.0885(5) 0.3908(2) 0.0520(13) Uani 1 1 d . . . C8 C 0.3499(7) 0.1287(8) 0.4647(3) 0.099(3) Uani 1 1 d . . . H8 H 0.2989 0.1272 0.4922 0.119 Uiso 1 1 calc R . . C9 C 0.4406(8) 0.1705(9) 0.4974(4) 0.122(4) Uani 1 1 d . . . H9 H 0.4527 0.1982 0.5482 0.149 Uiso 1 1 calc R . . C10 C 0.5120(6) 0.1728(7) 0.4587(3) 0.095(2) Uani 1 1 d . . . H10 H 0.5746 0.2023 0.4820 0.114 Uiso 1 1 calc R . . C11 C 0.4956(4) 0.1325(5) 0.3845(3) 0.0554(14) Uani 1 1 d . . . C12 C 0.5720(4) 0.1393(5) 0.3393(3) 0.0597(14) Uani 1 1 d . . . H12A H 0.5845 0.0574 0.3215 0.072 Uiso 1 1 calc R . . H12B H 0.6320 0.1720 0.3703 0.072 Uiso 1 1 calc R . . H12C H 0.5503 0.1930 0.2958 0.072 Uiso 1 1 calc R . . C13 C 0.2559(4) 0.3139(4) 0.2285(3) 0.0513(12) Uani 1 1 d . . . H13A H 0.2051 0.2516 0.2258 0.063 Uiso 1 1 calc R . . H13B H 0.2255 0.3945 0.2188 0.063 Uiso 1 1 calc R . . H13C H 0.2978 0.3131 0.2789 0.063 Uiso 1 1 calc R . . C14 C 0.3155(3) 0.2877(4) 0.1712(2) 0.0360(9) Uani 1 1 d . . . C15 C 0.3237(3) 0.3737(4) 0.1163(3) 0.0486(12) Uani 1 1 d . . . H15 H 0.2896 0.4490 0.1142 0.059 Uiso 1 1 calc R . . C16 C 0.3812(4) 0.3493(5) 0.0655(3) 0.0528(13) Uani 1 1 d . . . H16 H 0.3859 0.4071 0.0272 0.064 Uiso 1 1 calc R . . C17 C 0.4316(3) 0.2434(4) 0.0694(2) 0.0438(11) Uani 1 1 d . . . H17 H 0.4723 0.2266 0.0345 0.052 Uiso 1 1 calc R . . C18 C 0.4228(3) 0.1604(4) 0.1247(2) 0.0284(8) Uani 1 1 d . . . C19 C 0.4822(3) 0.0494(4) 0.1381(2) 0.0290(8) Uani 1 1 d . . . C20 C 0.5513(3) 0.0184(5) 0.0960(2) 0.0403(10) Uani 1 1 d . . . H20 H 0.5599 0.0673 0.0545 0.050 Uiso 1 1 calc R . . C21 C 0.6068(3) -0.0838(5) 0.1154(3) 0.0499(13) Uani 1 1 d . . . H21 H 0.6525 -0.1087 0.0861 0.059 Uiso 1 1 calc R . . C22 C 0.5960(3) -0.1496(5) 0.1771(3) 0.0459(11) Uani 1 1 d . . . H22 H 0.6361 -0.2189 0.1919 0.055 Uiso 1 1 calc R . . C23 C 0.5275(3) -0.1163(4) 0.2181(2) 0.0348(9) Uani 1 1 d . . . C24 C 0.5190(3) -0.1853(4) 0.2872(2) 0.0441(11) Uani 1 1 d . . . H24A H 0.4527 -0.2178 0.2818 0.054 Uiso 1 1 calc R . . H24B H 0.5328 -0.1307 0.3310 0.054 Uiso 1 1 calc R . . H24C H 0.5657 -0.2529 0.2946 0.054 Uiso 1 1 calc R . . H01A H 0.3263 -0.2007 0.1985 0.047 Uiso 1 1 d . . . H01B H 0.3030 -0.1862 0.2672 0.047 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0221(2) 0.0242(2) 0.0275(2) 0.00073(18) 0.00829(15) -0.00009(19) Cl1 0.0377(6) 0.0477(7) 0.0392(6) 0.0011(4) 0.0134(4) -0.0051(5) Cl2 0.0335(6) 0.0352(6) 0.0352(5) 0.0034(4) 0.0094(4) -0.0080(4) O1 0.0342(17) 0.0276(16) 0.0499(17) -0.0033(12) 0.0166(12) -0.0033(12) O11 0.138(4) 0.057(3) 0.086(3) 0.001(2) 0.052(3) 0.015(3) O12 0.089(4) 0.104(4) 0.075(3) -0.022(3) -0.033(2) 0.017(3) O13 0.096(3) 0.072(3) 0.055(2) -0.0112(19) 0.037(2) -0.014(2) O14 0.067(3) 0.118(4) 0.127(4) 0.002(3) 0.056(3) -0.036(3) O21 0.075(3) 0.044(2) 0.070(2) 0.0201(17) -0.0030(18) -0.0184(18) O22 0.039(2) 0.095(3) 0.087(3) 0.010(2) 0.0293(19) 0.002(2) O23 0.101(3) 0.041(2) 0.0389(18) -0.0004(14) 0.0280(17) -0.0042(18) O24 0.044(2) 0.055(2) 0.059(2) -0.0009(16) -0.0047(15) -0.0125(16) N1 0.032(2) 0.025(2) 0.048(2) 0.0003(13) 0.0186(14) -0.0012(13) N2 0.049(2) 0.034(2) 0.0296(18) -0.0034(14) 0.0044(15) -0.0010(16) N3 0.0221(17) 0.0248(18) 0.0322(16) 0.0028(12) 0.0055(11) -0.0032(12) N4 0.0211(16) 0.0283(17) 0.0297(15) -0.0043(13) 0.0051(11) 0.0000(13) C1 0.032(3) 0.050(3) 0.080(4) 0.006(3) -0.008(2) -0.003(2) C2 0.026(2) 0.031(2) 0.080(3) 0.001(2) 0.016(2) 0.0008(19) C3 0.038(3) 0.041(4) 0.141(6) 0.005(3) 0.038(3) -0.003(2) C4 0.070(5) 0.042(3) 0.161(7) 0.005(4) 0.087(5) -0.002(3) C5 0.106(6) 0.040(3) 0.109(5) -0.001(3) 0.090(5) -0.001(3) C6 0.063(3) 0.027(2) 0.052(3) 0.0042(17) 0.037(2) 0.006(2) C7 0.088(4) 0.040(3) 0.032(2) -0.0014(19) 0.022(2) 0.000(3) C8 0.145(8) 0.124(7) 0.036(3) -0.023(3) 0.039(4) -0.013(5) C9 0.176(10) 0.157(9) 0.026(3) -0.032(4) 0.008(4) -0.038(7) C10 0.128(7) 0.099(6) 0.044(4) -0.028(3) -0.015(4) -0.018(5) C11 0.070(4) 0.044(3) 0.042(3) -0.010(2) -0.012(2) -0.002(2) C12 0.041(3) 0.050(3) 0.080(4) -0.016(3) -0.006(2) -0.012(2) C13 0.050(3) 0.028(3) 0.082(4) 0.001(2) 0.028(2) 0.010(2) C14 0.027(2) 0.027(2) 0.051(2) 0.0055(17) 0.0007(16) -0.0026(16) C15 0.036(3) 0.035(3) 0.069(3) 0.017(2) -0.003(2) -0.0061(19) C16 0.058(3) 0.049(3) 0.049(3) 0.021(2) 0.005(2) -0.015(2) C17 0.047(3) 0.047(3) 0.037(2) 0.0081(19) 0.0084(18) -0.018(2) C18 0.026(2) 0.030(2) 0.0285(19) 0.0005(14) 0.0038(14) -0.0118(15) C19 0.024(2) 0.036(2) 0.0282(19) -0.0046(14) 0.0070(14) -0.0064(15) C20 0.027(2) 0.055(3) 0.042(2) -0.014(2) 0.0159(17) -0.015(2) C21 0.025(2) 0.063(3) 0.064(3) -0.032(3) 0.015(2) -0.004(2) C22 0.026(2) 0.047(3) 0.064(3) -0.021(2) 0.0082(19) 0.0035(19) C23 0.023(2) 0.026(2) 0.052(2) -0.0090(17) 0.0013(16) 0.0004(15) C24 0.041(3) 0.034(3) 0.053(3) 0.0046(19) -0.0014(19) 0.0089(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 1.975(3) . ? Cu1 N1 1.989(3) . ? Cu1 O1 2.057(3) . ? Cu1 N3 2.057(3) . ? Cu1 N2 2.138(3) . ? Cl1 O12 1.394(4) . ? Cl1 O14 1.403(4) . ? Cl1 O11 1.419(5) . ? Cl1 O13 1.420(4) . ? Cl2 O21 1.411(4) . ? Cl2 O24 1.412(3) . ? Cl2 O22 1.424(4) . ? Cl2 O23 1.439(3) . ? O1 H01A 0.824(3) . ? O1 H01B 0.890(3) . ? N1 C6 1.342(6) . ? N1 C2 1.345(6) . ? N2 C11 1.354(6) . ? N2 C7 1.354(6) . ? N3 C14 1.346(5) . ? N3 C18 1.353(5) . ? N4 C19 1.338(5) . ? N4 C23 1.347(5) . ? C1 C2 1.486(7) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.375(7) . ? C3 C4 1.379(10) . ? C3 H3 0.9500 . ? C4 C5 1.335(10) . ? C4 H4 0.9500 . ? C5 C6 1.393(6) . ? C5 H5 0.9500 . ? C6 C7 1.473(8) . ? C7 C8 1.382(7) . ? C8 C9 1.368(12) . ? C8 H8 0.9500 . ? C9 C10 1.332(11) . ? C9 H9 0.9500 . ? C10 C11 1.387(7) . ? C10 H10 0.9500 . ? C11 C12 1.474(8) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.485(6) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.390(6) . ? C15 C16 1.364(7) . ? C15 H15 0.9500 . ? C16 C17 1.352(7) . ? C16 H16 0.9500 . ? C17 C18 1.377(5) . ? C17 H17 0.9500 . ? C18 C19 1.465(6) . ? C19 C20 1.389(5) . ? C20 C21 1.368(7) . ? C20 H20 0.9500 . ? C21 C22 1.362(7) . ? C21 H21 0.9500 . ? C22 C23 1.375(6) . ? C22 H22 0.9500 . ? C23 C24 1.487(6) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 N4 Cu1 N1 169.60(14) . . ? N4 Cu1 O1 89.52(12) . . ? N1 Cu1 O1 80.48(12) . . ? N4 Cu1 N3 81.41(13) . . ? N1 Cu1 N3 104.19(13) . . ? O1 Cu1 N3 138.52(12) . . ? N4 Cu1 N2 107.42(13) . . ? N1 Cu1 N2 80.00(15) . . ? O1 Cu1 N2 117.29(13) . . ? N3 Cu1 N2 104.02(13) . . ? O12 Cl1 O14 109.2(3) . . ? O12 Cl1 O11 109.9(3) . . ? O14 Cl1 O11 110.4(3) . . ? O12 Cl1 O13 110.3(3) . . ? O14 Cl1 O13 108.5(3) . . ? O11 Cl1 O13 108.4(2) . . ? O21 Cl2 O24 111.5(2) . . ? O21 Cl2 O22 109.9(2) . . ? O24 Cl2 O22 109.1(2) . . ? O21 Cl2 O23 110.0(2) . . ? O24 Cl2 O23 109.0(2) . . ? O22 Cl2 O23 107.2(2) . . ? Cu1 O1 H01A 124.6(2) . . ? Cu1 O1 H01B 113.0(2) . . ? H01A O1 H01B 104.5(3) . . ? C6 N1 C2 120.8(4) . . ? C6 N1 Cu1 114.6(3) . . ? C2 N1 Cu1 123.1(3) . . ? C11 N2 C7 119.5(4) . . ? C11 N2 Cu1 129.5(3) . . ? C7 N2 Cu1 110.8(3) . . ? C14 N3 C18 119.1(3) . . ? C14 N3 Cu1 130.1(3) . . ? C18 N3 Cu1 110.6(2) . . ? C19 N4 C23 120.3(3) . . ? C19 N4 Cu1 113.7(3) . . ? C23 N4 Cu1 125.7(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 119.6(5) . . ? N1 C2 C1 117.9(4) . . ? C3 C2 C1 122.4(5) . . ? C2 C3 C4 119.7(6) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 120.2(5) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.3(6) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? N1 C6 C5 120.3(6) . . ? N1 C6 C7 116.4(4) . . ? C5 C6 C7 123.3(5) . . ? N2 C7 C8 120.9(6) . . ? N2 C7 C6 115.3(4) . . ? C8 C7 C6 123.5(6) . . ? C9 C8 C7 118.7(7) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C10 C9 C8 120.6(6) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 120.5(7) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? N2 C11 C10 119.8(6) . . ? N2 C11 C12 118.6(4) . . ? C10 C11 C12 121.6(6) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 C15 120.2(4) . . ? N3 C14 C13 119.3(4) . . ? C15 C14 C13 120.5(4) . . ? C16 C15 C14 119.6(5) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C17 C16 C15 120.4(4) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 118.8(4) . . ? C16 C17 H17 120.6 . . ? C18 C17 H17 120.6 . . ? N3 C18 C17 121.8(4) . . ? N3 C18 C19 115.5(3) . . ? C17 C18 C19 122.5(4) . . ? N4 C19 C20 120.9(4) . . ? N4 C19 C18 115.8(3) . . ? C20 C19 C18 123.2(4) . . ? C21 C20 C19 118.8(4) . . ? C21 C20 H20 120.6 . . ? C19 C20 H20 120.6 . . ? C22 C21 C20 119.5(4) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C21 C22 C23 120.4(5) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? N4 C23 C22 119.9(4) . . ? N4 C23 C24 119.9(4) . . ? C22 C23 C24 120.1(4) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 N4 Cu1 N1 C6 120.6(7) . . . . ? O1 Cu1 N1 C6 104.4(3) . . . . ? N3 Cu1 N1 C6 -117.8(3) . . . . ? N2 Cu1 N1 C6 -15.7(3) . . . . ? N4 Cu1 N1 C2 -45.3(9) . . . . ? O1 Cu1 N1 C2 -61.5(3) . . . . ? N3 Cu1 N1 C2 76.3(3) . . . . ? N2 Cu1 N1 C2 178.4(4) . . . . ? N4 Cu1 N2 C11 22.5(4) . . . . ? N1 Cu1 N2 C11 -165.0(4) . . . . ? O1 Cu1 N2 C11 121.2(4) . . . . ? N3 Cu1 N2 C11 -62.8(4) . . . . ? N4 Cu1 N2 C7 -162.1(3) . . . . ? N1 Cu1 N2 C7 10.4(3) . . . . ? O1 Cu1 N2 C7 -63.3(3) . . . . ? N3 Cu1 N2 C7 112.7(3) . . . . ? N4 Cu1 N3 C14 -170.2(4) . . . . ? N1 Cu1 N3 C14 18.7(4) . . . . ? O1 Cu1 N3 C14 110.4(3) . . . . ? N2 Cu1 N3 C14 -64.3(4) . . . . ? N4 Cu1 N3 C18 14.6(2) . . . . ? N1 Cu1 N3 C18 -156.4(2) . . . . ? O1 Cu1 N3 C18 -64.8(3) . . . . ? N2 Cu1 N3 C18 120.6(3) . . . . ? N1 Cu1 N4 C19 108.6(8) . . . . ? O1 Cu1 N4 C19 124.6(3) . . . . ? N3 Cu1 N4 C19 -14.8(3) . . . . ? N2 Cu1 N4 C19 -116.8(3) . . . . ? N1 Cu1 N4 C23 -64.7(8) . . . . ? O1 Cu1 N4 C23 -48.7(3) . . . . ? N3 Cu1 N4 C23 171.9(3) . . . . ? N2 Cu1 N4 C23 69.9(3) . . . . ? C6 N1 C2 C3 -1.3(7) . . . . ? Cu1 N1 C2 C3 163.7(4) . . . . ? C6 N1 C2 C1 178.4(4) . . . . ? Cu1 N1 C2 C1 -16.5(6) . . . . ? N1 C2 C3 C4 -1.5(8) . . . . ? C1 C2 C3 C4 178.8(5) . . . . ? C2 C3 C4 C5 2.8(9) . . . . ? C3 C4 C5 C6 -1.4(9) . . . . ? C2 N1 C6 C5 2.8(6) . . . . ? Cu1 N1 C6 C5 -163.5(4) . . . . ? C2 N1 C6 C7 -175.2(4) . . . . ? Cu1 N1 C6 C7 18.6(5) . . . . ? C4 C5 C6 N1 -1.4(8) . . . . ? C4 C5 C6 C7 176.4(5) . . . . ? C11 N2 C7 C8 -1.8(8) . . . . ? Cu1 N2 C7 C8 -177.7(5) . . . . ? C11 N2 C7 C6 172.1(4) . . . . ? Cu1 N2 C7 C6 -3.9(5) . . . . ? N1 C6 C7 N2 -9.2(6) . . . . ? C5 C6 C7 N2 172.9(4) . . . . ? N1 C6 C7 C8 164.4(6) . . . . ? C5 C6 C7 C8 -13.4(9) . . . . ? N2 C7 C8 C9 0.8(11) . . . . ? C6 C7 C8 C9 -172.5(7) . . . . ? C7 C8 C9 C10 0.2(14) . . . . ? C8 C9 C10 C11 -0.1(14) . . . . ? C7 N2 C11 C10 1.8(8) . . . . ? Cu1 N2 C11 C10 176.9(5) . . . . ? C7 N2 C11 C12 -176.3(5) . . . . ? Cu1 N2 C11 C12 -1.2(7) . . . . ? C9 C10 C11 N2 -0.9(11) . . . . ? C9 C10 C11 C12 177.1(7) . . . . ? C18 N3 C14 C15 2.8(6) . . . . ? Cu1 N3 C14 C15 -172.0(3) . . . . ? C18 N3 C14 C13 -175.6(4) . . . . ? Cu1 N3 C14 C13 9.6(6) . . . . ? N3 C14 C15 C16 -0.4(7) . . . . ? C13 C14 C15 C16 178.0(5) . . . . ? C14 C15 C16 C17 -1.4(7) . . . . ? C15 C16 C17 C18 0.8(7) . . . . ? C14 N3 C18 C17 -3.4(6) . . . . ? Cu1 N3 C18 C17 172.3(3) . . . . ? C14 N3 C18 C19 172.0(3) . . . . ? Cu1 N3 C18 C19 -12.3(4) . . . . ? C16 C17 C18 N3 1.7(6) . . . . ? C16 C17 C18 C19 -173.4(4) . . . . ? C23 N4 C19 C20 2.6(6) . . . . ? Cu1 N4 C19 C20 -171.1(3) . . . . ? C23 N4 C19 C18 -174.0(3) . . . . ? Cu1 N4 C19 C18 12.3(4) . . . . ? N3 C18 C19 N4 0.5(5) . . . . ? C17 C18 C19 N4 175.9(4) . . . . ? N3 C18 C19 C20 -175.9(4) . . . . ? C17 C18 C19 C20 -0.6(6) . . . . ? N4 C19 C20 C21 0.3(6) . . . . ? C18 C19 C20 C21 176.6(4) . . . . ? C19 C20 C21 C22 -2.7(7) . . . . ? C20 C21 C22 C23 2.3(7) . . . . ? C19 N4 C23 C22 -3.0(6) . . . . ? Cu1 N4 C23 C22 169.9(3) . . . . ? C19 N4 C23 C24 174.9(4) . . . . ? Cu1 N4 C23 C24 -12.2(5) . . . . ? C21 C22 C23 N4 0.6(7) . . . . ? C21 C22 C23 C24 -177.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.472 _refine_diff_density_min -0.541 _refine_diff_density_rms 0.096 data_Cudmbp _database_code_depnum_ccdc_archive 'CCDC 251496' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(6,6'-dimethyl-2,2'-bipyridine)copper(II) perchlorate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 Cu N4 2+, 2(Cl O4, 1-)' _chemical_formula_sum 'C24 H24 Cl2 Cu N4 O8' _chemical_formula_weight 630.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 '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' O O 0.0106 0.0060 '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' 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.939(8) _cell_length_b 14.511(11) _cell_length_c 19.074(17) _cell_angle_alpha 74.06(8) _cell_angle_beta 86.30(7) _cell_angle_gamma 78.02(7) _cell_volume 2587(4) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 19025 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description columnar _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1292 _exptl_absorpt_coefficient_mu 1.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.642 _exptl_absorpt_correction_T_max 0.801 _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_special_details none _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22771 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.49 _reflns_number_total 10610 _reflns_number_gt 7911 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ORTEP _computing_publication_material SHELXL-97 _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^)+(0.0591P)^2^+0.5201P] 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 10610 _refine_ls_number_parameters 703 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.0998 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.62483(3) 0.06226(2) 0.712922(19) 0.03563(10) Uani 1 1 d . . . Cu2 Cu 0.96990(4) 0.46009(2) 0.79475(2) 0.03807(10) Uani 1 1 d . . . Cl1 Cl 0.31238(8) -0.10845(5) 0.85134(4) 0.04036(17) Uani 1 1 d . . . Cl2 Cl 0.87759(8) 0.17003(5) 0.54646(4) 0.04018(17) Uani 1 1 d . . . Cl3 Cl 0.64197(8) 0.59543(5) 0.60633(4) 0.04157(17) Uani 1 1 d . . . Cl4 Cl 1.25150(7) 0.36134(5) 0.95989(4) 0.03675(16) Uani 1 1 d . . . O1 O 0.3068(4) -0.01012(19) 0.84997(17) 0.1016(12) Uani 1 1 d . . . O2 O 0.3643(3) -0.1254(2) 0.78409(14) 0.0772(8) Uani 1 1 d . . . O3 O 0.3962(2) -0.17061(19) 0.91047(13) 0.0619(7) Uani 1 1 d . . . O4 O 0.1781(3) -0.1308(2) 0.86187(16) 0.0811(9) Uani 1 1 d . . . O5 O 0.8284(3) 0.0983(2) 0.52369(13) 0.0680(8) Uani 1 1 d . . . O6 O 0.8109(3) 0.17889(18) 0.61475(13) 0.0677(7) Uani 1 1 d . . . O7 O 0.8470(3) 0.26169(18) 0.49360(15) 0.0776(8) Uani 1 1 d . . . O8 O 1.0201(3) 0.1422(2) 0.55715(19) 0.0908(10) Uani 1 1 d . . . O9 O 0.6422(3) 0.5281(2) 0.56383(14) 0.0784(9) Uani 1 1 d . . . O10 O 0.6446(4) 0.5453(2) 0.68209(14) 0.0921(11) Uani 1 1 d . . . O11 O 0.5205(3) 0.6680(2) 0.5920(2) 0.0964(11) Uani 1 1 d . . . O12 O 0.7558(3) 0.6426(2) 0.58656(15) 0.0690(8) Uani 1 1 d . . . O13 O 1.1433(3) 0.3108(2) 0.98939(14) 0.0620(7) Uani 1 1 d . . . O14 O 1.2564(3) 0.43375(18) 0.99714(14) 0.0660(7) Uani 1 1 d . . . O15 O 1.2282(3) 0.40744(16) 0.88366(12) 0.0626(7) Uani 1 1 d . . . O16 O 1.3790(3) 0.29301(19) 0.96930(15) 0.0734(8) Uani 1 1 d . . . N1 N 0.5263(2) 0.01219(16) 0.64611(11) 0.0294(5) Uani 1 1 d . . . N2 N 0.7850(2) -0.02803(15) 0.68919(12) 0.0299(5) Uani 1 1 d . . . N3 N 0.6328(2) 0.03593(15) 0.82133(12) 0.0278(5) Uani 1 1 d . . . N4 N 0.5465(2) 0.19814(15) 0.71780(13) 0.0314(5) Uani 1 1 d . . . N5 N 0.7891(2) 0.50388(16) 0.84025(12) 0.0304(5) Uani 1 1 d . . . N6 N 0.9526(2) 0.32957(15) 0.85790(12) 0.0308(5) Uani 1 1 d . . . N7 N 1.0206(2) 0.44466(15) 0.69605(12) 0.0290(5) Uani 1 1 d . . . N8 N 1.0805(2) 0.56293(14) 0.76725(12) 0.0270(4) Uani 1 1 d . . . C1 C 0.2966(3) 0.1066(2) 0.66115(18) 0.0452(7) Uani 1 1 d . . . H1A H 0.3215 0.1705 0.6406 0.055 Uiso 1 1 calc R . . H1B H 0.3045 0.0884 0.7144 0.055 Uiso 1 1 calc R . . H1C H 0.2016 0.1098 0.6480 0.055 Uiso 1 1 calc R . . C2 C 0.3912(3) 0.0317(2) 0.63137(15) 0.0348(6) Uani 1 1 d . . . C3 C 0.3388(3) -0.0200(2) 0.59100(16) 0.0417(7) Uani 1 1 d . . . H3 H 0.2442 -0.0036 0.5785 0.051 Uiso 1 1 calc R . . C4 C 0.4253(4) -0.0945(2) 0.56960(17) 0.0485(8) Uani 1 1 d . . . H4 H 0.3901 -0.1312 0.5433 0.058 Uiso 1 1 calc R . . C5 C 0.5629(3) -0.1160(2) 0.58628(17) 0.0425(7) Uani 1 1 d . . . H5 H 0.6233 -0.1680 0.5723 0.051 Uiso 1 1 calc R . . C6 C 0.6118(3) -0.06082(19) 0.62373(14) 0.0317(6) Uani 1 1 d . . . C7 C 0.7581(3) -0.07761(18) 0.64360(14) 0.0304(6) Uani 1 1 d . . . C8 C 0.8620(3) -0.1393(2) 0.61702(16) 0.0414(7) Uani 1 1 d . . . H8 H 0.8422 -0.1742 0.5848 0.049 Uiso 1 1 calc R . . C9 C 0.9957(3) -0.1485(2) 0.63882(18) 0.0485(8) Uani 1 1 d . . . H9 H 1.0688 -0.1911 0.6221 0.057 Uiso 1 1 calc R . . C10 C 1.0225(3) -0.0962(2) 0.68458(18) 0.0439(7) Uani 1 1 d . . . H10 H 1.1142 -0.1025 0.6994 0.053 Uiso 1 1 calc R . . C11 C 0.9165(3) -0.0344(2) 0.70917(15) 0.0350(6) Uani 1 1 d . . . C12 C 0.9428(3) 0.0257(2) 0.75701(18) 0.0458(7) Uani 1 1 d . . . H12A H 0.9109 -0.0013 0.8067 0.056 Uiso 1 1 calc R . . H12B H 0.8932 0.0932 0.7382 0.056 Uiso 1 1 calc R . . H12C H 1.0416 0.0247 0.7575 0.056 Uiso 1 1 calc R . . C13 C 0.7048(3) -0.1424(2) 0.84557(17) 0.0418(7) Uani 1 1 d . . . H13A H 0.6440 -0.1361 0.8053 0.052 Uiso 1 1 calc R . . H13B H 0.6915 -0.1984 0.8860 0.052 Uiso 1 1 calc R . . H13C H 0.8007 -0.1524 0.8289 0.052 Uiso 1 1 calc R . . C14 C 0.6713(3) -0.05124(19) 0.87077(15) 0.0319(6) Uani 1 1 d . . . C15 C 0.6796(3) -0.0562(2) 0.94428(16) 0.0394(7) Uani 1 1 d . . . H15 H 0.7104 -0.1174 0.9784 0.047 Uiso 1 1 calc R . . C16 C 0.6435(3) 0.0266(2) 0.96748(16) 0.0414(7) Uani 1 1 d . . . H16 H 0.6499 0.0234 1.0176 0.049 Uiso 1 1 calc R . . C17 C 0.5974(3) 0.1152(2) 0.91726(16) 0.0382(7) Uani 1 1 d . . . H17 H 0.5687 0.1734 0.9325 0.046 Uiso 1 1 calc R . . C18 C 0.5939(3) 0.11753(19) 0.84455(15) 0.0297(6) Uani 1 1 d . . . C19 C 0.5496(2) 0.20867(19) 0.78613(16) 0.0307(6) Uani 1 1 d . . . C20 C 0.5134(3) 0.2990(2) 0.80037(19) 0.0423(7) Uani 1 1 d . . . H20 H 0.5135 0.3045 0.8489 0.052 Uiso 1 1 calc R . . C21 C 0.4770(3) 0.3813(2) 0.7430(2) 0.0495(8) Uani 1 1 d . . . H21 H 0.4521 0.4442 0.7514 0.061 Uiso 1 1 calc R . . C22 C 0.4773(3) 0.3709(2) 0.6741(2) 0.0488(8) Uani 1 1 d . . . H22 H 0.4540 0.4273 0.6342 0.057 Uiso 1 1 calc R . . C23 C 0.5117(3) 0.2783(2) 0.66132(17) 0.0396(7) Uani 1 1 d . . . C24 C 0.5109(4) 0.2685(3) 0.58562(18) 0.0562(9) Uani 1 1 d . . . H24A H 0.4460 0.2272 0.5829 0.069 Uiso 1 1 calc R . . H24B H 0.6033 0.2386 0.5724 0.069 Uiso 1 1 calc R . . H24C H 0.4827 0.3333 0.5518 0.069 Uiso 1 1 calc R . . C25 C 0.7539(3) 0.6715(2) 0.76181(17) 0.0408(7) Uani 1 1 d . . . H25A H 0.8188 0.6983 0.7832 0.049 Uiso 1 1 calc R . . H25B H 0.6750 0.7234 0.7421 0.049 Uiso 1 1 calc R . . H25C H 0.7997 0.6449 0.7225 0.049 Uiso 1 1 calc R . . C26 C 0.7054(3) 0.5920(2) 0.81899(15) 0.0353(6) Uani 1 1 d . . . C27 C 0.5737(3) 0.6071(3) 0.84914(17) 0.0449(8) Uani 1 1 d . . . H27 H 0.5151 0.6697 0.8351 0.053 Uiso 1 1 calc R . . C28 C 0.5290(3) 0.5316(3) 0.89909(18) 0.0506(9) Uani 1 1 d . . . H28 H 0.4391 0.5417 0.9194 0.060 Uiso 1 1 calc R . . C29 C 0.6147(3) 0.4410(3) 0.91980(16) 0.0425(7) Uani 1 1 d . . . H29 H 0.5847 0.3880 0.9541 0.053 Uiso 1 1 calc R . . C30 C 0.7459(3) 0.4292(2) 0.88925(14) 0.0330(6) Uani 1 1 d . . . C31 C 0.8433(3) 0.3341(2) 0.90417(15) 0.0338(6) Uani 1 1 d . . . C32 C 0.8252(4) 0.2532(2) 0.95979(17) 0.0474(8) Uani 1 1 d . . . H32 H 0.7504 0.2577 0.9931 0.058 Uiso 1 1 calc R . . C33 C 0.9171(4) 0.1665(2) 0.9662(2) 0.0574(9) Uani 1 1 d . . . H33 H 0.9057 0.1102 1.0039 0.070 Uiso 1 1 calc R . . C34 C 1.0248(4) 0.1612(2) 0.91815(19) 0.0493(8) Uani 1 1 d . . . H34 H 1.0867 0.1008 0.9214 0.059 Uiso 1 1 calc R . . C35 C 1.0436(3) 0.24458(19) 0.86459(16) 0.0362(6) Uani 1 1 d . . . C36 C 1.1654(3) 0.2415(2) 0.81459(19) 0.0476(8) Uani 1 1 d . . . H36A H 1.2073 0.2980 0.8111 0.059 Uiso 1 1 calc R . . H36B H 1.1361 0.2432 0.7661 0.059 Uiso 1 1 calc R . . H36C H 1.2328 0.1812 0.8337 0.059 Uiso 1 1 calc R . . C37 C 0.8614(4) 0.3346(3) 0.6995(2) 0.0545(9) Uani 1 1 d . . . H37A H 0.7990 0.3751 0.7262 0.066 Uiso 1 1 calc R . . H37B H 0.9039 0.2731 0.7337 0.066 Uiso 1 1 calc R . . H37C H 0.8095 0.3206 0.6629 0.066 Uiso 1 1 calc R . . C38 C 0.9707(3) 0.3880(2) 0.66243(16) 0.0390(7) Uani 1 1 d . . . C39 C 1.0212(4) 0.3809(2) 0.59438(18) 0.0490(8) Uani 1 1 d . . . H39 H 0.9900 0.3387 0.5716 0.058 Uiso 1 1 calc R . . C40 C 1.1157(4) 0.4345(3) 0.56008(17) 0.0517(9) Uani 1 1 d . . . H40 H 1.1520 0.4283 0.5139 0.061 Uiso 1 1 calc R . . C41 C 1.1590(3) 0.4980(2) 0.59225(15) 0.0416(7) Uani 1 1 d . . . H41 H 1.2208 0.5383 0.5675 0.050 Uiso 1 1 calc R . . C42 C 1.1099(3) 0.50129(19) 0.66139(14) 0.0299(6) Uani 1 1 d . . . C43 C 1.1480(2) 0.56452(18) 0.70265(14) 0.0284(5) Uani 1 1 d . . . C44 C 1.2487(3) 0.6202(2) 0.67846(17) 0.0390(7) Uani 1 1 d . . . H44 H 1.2952 0.6203 0.6334 0.047 Uiso 1 1 calc R . . C45 C 1.2788(3) 0.6747(2) 0.7213(2) 0.0478(8) Uani 1 1 d . . . H45 H 1.3471 0.7134 0.7059 0.058 Uiso 1 1 calc R . . C46 C 1.2111(3) 0.6738(2) 0.7862(2) 0.0474(8) Uani 1 1 d . . . H46 H 1.2319 0.7124 0.8154 0.057 Uiso 1 1 calc R . . C47 C 1.1113(3) 0.61619(18) 0.80978(16) 0.0349(6) Uani 1 1 d . . . C48 C 1.0396(3) 0.6130(2) 0.88099(17) 0.0463(8) Uani 1 1 d . . . H48A H 0.9399 0.6303 0.8734 0.057 Uiso 1 1 calc R . . H48B H 1.0678 0.6596 0.9029 0.057 Uiso 1 1 calc R . . H48C H 1.0637 0.5469 0.9136 0.057 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 0.03488(19) 0.03694(18) 0.03307(19) -0.01621(15) -0.01037(14) 0.00967(14) Cu2 0.0554(2) 0.02551(16) 0.0382(2) -0.01498(15) 0.02631(16) -0.01845(15) Cl1 0.0524(4) 0.0382(4) 0.0302(4) -0.0087(3) -0.0034(3) -0.0080(3) Cl2 0.0495(4) 0.0325(3) 0.0394(4) -0.0066(3) -0.0138(3) -0.0099(3) Cl3 0.0550(4) 0.0427(4) 0.0323(4) -0.0116(3) 0.0090(3) -0.0221(3) Cl4 0.0449(4) 0.0322(3) 0.0306(3) -0.0072(3) -0.0021(3) -0.0031(3) O1 0.202(4) 0.0406(14) 0.066(2) -0.0127(14) -0.032(2) -0.0255(19) O2 0.116(2) 0.0786(19) 0.0374(14) -0.0181(14) 0.0161(14) -0.0210(17) O3 0.0520(14) 0.0723(16) 0.0426(14) 0.0076(12) -0.0024(11) -0.0006(12) O4 0.0554(17) 0.118(3) 0.0640(18) -0.0116(18) -0.0085(14) -0.0197(16) O5 0.105(2) 0.0709(16) 0.0477(14) -0.0224(13) -0.0017(14) -0.0526(16) O6 0.112(2) 0.0474(13) 0.0418(14) -0.0145(12) -0.0052(14) -0.0078(14) O7 0.110(2) 0.0460(14) 0.0573(17) 0.0135(13) -0.0040(16) -0.0077(14) O8 0.0552(17) 0.104(2) 0.113(3) -0.027(2) -0.0303(17) -0.0081(16) O9 0.132(3) 0.0772(18) 0.0528(16) -0.0345(15) 0.0176(16) -0.0624(18) O10 0.175(3) 0.081(2) 0.0364(14) -0.0050(14) -0.0044(17) -0.075(2) O11 0.0593(18) 0.099(2) 0.124(3) -0.030(2) 0.0203(18) -0.0050(16) O12 0.0674(16) 0.0847(19) 0.0782(19) -0.0470(16) 0.0347(14) -0.0436(14) O13 0.0595(15) 0.0797(18) 0.0554(15) -0.0178(14) 0.0031(12) -0.0343(13) O14 0.098(2) 0.0575(15) 0.0532(15) -0.0252(13) -0.0189(14) -0.0201(14) O15 0.110(2) 0.0379(12) 0.0320(12) -0.0042(10) -0.0056(12) -0.0018(12) O16 0.0577(15) 0.0635(16) 0.0681(18) 0.0094(14) 0.0117(13) 0.0166(12) N1 0.0310(12) 0.0328(11) 0.0229(11) -0.0050(9) -0.0003(9) -0.0065(9) N2 0.0307(12) 0.0278(11) 0.0271(12) -0.0041(9) 0.0023(9) -0.0020(9) N3 0.0272(11) 0.0268(10) 0.0297(12) -0.0095(9) -0.0007(9) -0.0030(8) N4 0.0225(11) 0.0297(11) 0.0374(13) -0.0048(10) 0.0003(9) -0.0005(8) N5 0.0356(12) 0.0347(12) 0.0258(11) -0.0138(10) 0.0074(9) -0.0129(9) N6 0.0376(12) 0.0300(11) 0.0291(12) -0.0089(10) 0.0063(10) -0.0168(9) N7 0.0311(12) 0.0292(11) 0.0279(11) -0.0106(9) 0.0040(9) -0.0058(9) N8 0.0299(11) 0.0210(10) 0.0284(11) -0.0035(9) -0.0006(9) -0.0053(8) C1 0.0280(15) 0.061(2) 0.0451(18) -0.0143(16) -0.0026(13) -0.0044(13) C2 0.0341(15) 0.0447(16) 0.0233(13) -0.0026(12) -0.0009(11) -0.0115(12) C3 0.0415(17) 0.0541(18) 0.0304(15) -0.0041(14) -0.0050(13) -0.0193(14) C4 0.065(2) 0.0528(19) 0.0367(17) -0.0150(15) -0.0023(15) -0.0266(16) C5 0.0540(19) 0.0397(16) 0.0366(16) -0.0131(14) -0.0011(14) -0.0115(13) C6 0.0423(15) 0.0309(13) 0.0212(13) -0.0047(11) 0.0043(11) -0.0096(11) C7 0.0359(14) 0.0245(12) 0.0252(13) -0.0004(11) 0.0038(11) -0.0029(10) C8 0.0513(18) 0.0324(14) 0.0349(16) -0.0091(13) 0.0077(13) 0.0016(13) C9 0.0413(18) 0.0444(17) 0.0449(18) -0.0036(15) 0.0095(14) 0.0105(13) C10 0.0319(15) 0.0434(16) 0.0458(18) -0.0018(14) 0.0027(13) 0.0013(12) C11 0.0301(14) 0.0329(14) 0.0335(15) 0.0029(12) -0.0008(12) -0.0034(11) C12 0.0354(16) 0.0512(18) 0.0504(19) -0.0118(16) -0.0099(14) -0.0073(13) C13 0.0567(19) 0.0275(13) 0.0384(17) -0.0076(13) 0.0040(14) -0.0049(12) C14 0.0353(14) 0.0286(13) 0.0315(14) -0.0074(11) 0.0007(11) -0.0067(11) C15 0.0456(17) 0.0384(15) 0.0315(15) -0.0052(13) -0.0018(13) -0.0073(13) C16 0.0486(18) 0.0494(17) 0.0301(15) -0.0143(14) -0.0020(13) -0.0127(14) C17 0.0420(16) 0.0396(15) 0.0398(16) -0.0225(14) 0.0016(13) -0.0079(12) C18 0.0245(13) 0.0309(13) 0.0357(15) -0.0126(12) 0.0010(11) -0.0050(10) C19 0.0224(12) 0.0287(13) 0.0415(16) -0.0115(12) 0.0034(11) -0.0045(10) C20 0.0350(15) 0.0334(15) 0.061(2) -0.0196(15) 0.0023(14) -0.0029(12) C21 0.0409(17) 0.0299(15) 0.075(3) -0.0118(16) 0.0033(16) -0.0053(12) C22 0.0306(15) 0.0296(14) 0.072(2) 0.0085(15) -0.0011(15) -0.0035(11) C23 0.0247(14) 0.0401(15) 0.0457(18) 0.0007(14) 0.0014(12) -0.0047(11) C24 0.051(2) 0.061(2) 0.0418(19) 0.0054(17) 0.0003(15) -0.0051(16) C25 0.0458(17) 0.0338(14) 0.0435(17) -0.0134(13) -0.0032(14) -0.0045(12) C26 0.0397(15) 0.0398(15) 0.0324(15) -0.0208(13) -0.0023(12) -0.0059(12) C27 0.0326(15) 0.063(2) 0.0435(18) -0.0276(16) -0.0023(13) -0.0009(14) C28 0.0332(16) 0.084(3) 0.0462(19) -0.0370(19) 0.0079(14) -0.0129(16) C29 0.0399(17) 0.066(2) 0.0330(16) -0.0241(15) 0.0116(13) -0.0257(15) C30 0.0390(15) 0.0433(15) 0.0243(13) -0.0162(12) 0.0072(11) -0.0177(12) C31 0.0401(15) 0.0387(14) 0.0286(14) -0.0110(12) 0.0044(12) -0.0202(12) C32 0.057(2) 0.0538(19) 0.0337(17) -0.0025(15) 0.0106(14) -0.0318(16) C33 0.078(3) 0.0420(18) 0.047(2) 0.0099(16) -0.0033(18) -0.0299(17) C34 0.061(2) 0.0311(15) 0.055(2) -0.0029(14) -0.0089(17) -0.0154(14) C35 0.0435(16) 0.0281(13) 0.0404(16) -0.0087(12) -0.0039(13) -0.0140(12) C36 0.0465(18) 0.0339(15) 0.062(2) -0.0152(15) 0.0046(16) -0.0049(13) C37 0.060(2) 0.054(2) 0.062(2) -0.0243(18) -0.0041(17) -0.0280(17) C38 0.0435(17) 0.0378(15) 0.0384(16) -0.0154(13) -0.0053(13) -0.0052(12) C39 0.060(2) 0.0504(18) 0.0403(18) -0.0233(16) -0.0047(15) -0.0027(16) C40 0.056(2) 0.068(2) 0.0265(15) -0.0203(16) -0.0020(14) 0.0091(17) C41 0.0349(16) 0.0514(17) 0.0275(15) -0.0006(14) 0.0072(12) 0.0001(13) C42 0.0256(13) 0.0331(13) 0.0257(13) -0.0035(11) 0.0019(10) -0.0002(10) C43 0.0247(13) 0.0248(12) 0.0293(14) 0.0029(11) -0.0009(10) -0.0039(10) C44 0.0292(14) 0.0344(14) 0.0453(18) 0.0043(13) -0.0019(13) -0.0080(11) C45 0.0366(16) 0.0337(15) 0.067(2) 0.0043(15) -0.0092(16) -0.0142(12) C46 0.0467(18) 0.0282(14) 0.069(2) -0.0115(15) -0.0262(17) -0.0041(13) C47 0.0372(15) 0.0243(12) 0.0415(16) -0.0094(12) -0.0119(12) 0.0020(11) C48 0.0564(19) 0.0444(17) 0.0396(17) -0.0230(14) -0.0115(15) 0.0058(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.955(3) . ? Cu1 N4 1.989(3) . ? Cu1 N3 2.001(3) . ? Cu1 N1 2.019(3) . ? Cu2 N8 1.972(3) . ? Cu2 N7 1.978(3) . ? Cu2 N6 1.981(3) . ? Cu2 N5 2.003(3) . ? Cl1 O1 1.409(3) . ? Cl1 O2 1.417(3) . ? Cl1 O3 1.425(3) . ? Cl1 O4 1.427(3) . ? Cl2 O8 1.402(3) . ? Cl2 O5 1.414(2) . ? Cl2 O7 1.419(3) . ? Cl2 O6 1.448(3) . ? Cl3 O11 1.414(3) . ? Cl3 O12 1.420(3) . ? Cl3 O10 1.427(3) . ? Cl3 O9 1.431(3) . ? Cl4 O16 1.425(3) . ? Cl4 O13 1.426(3) . ? Cl4 O14 1.431(3) . ? Cl4 O15 1.435(3) . ? N1 C2 1.346(4) . ? N1 C6 1.361(3) . ? N2 C7 1.341(4) . ? N2 C11 1.362(4) . ? N3 C18 1.350(3) . ? N3 C14 1.352(4) . ? N4 C23 1.351(4) . ? N4 C19 1.356(4) . ? N5 C26 1.345(4) . ? N5 C30 1.348(4) . ? N6 C35 1.350(4) . ? N6 C31 1.357(4) . ? N7 C42 1.352(4) . ? N7 C38 1.354(4) . ? N8 C47 1.350(3) . ? N8 C43 1.361(3) . ? C1 C2 1.495(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.398(4) . ? C3 C4 1.374(5) . ? C3 H3 0.9500 . ? C4 C5 1.376(5) . ? C4 H4 0.9500 . ? C5 C6 1.382(4) . ? C5 H5 0.9500 . ? C6 C7 1.480(4) . ? C7 C8 1.386(4) . ? C8 C9 1.387(5) . ? C8 H8 0.9500 . ? C9 C10 1.374(5) . ? C9 H9 0.9500 . ? C10 C11 1.381(4) . ? C10 H10 0.9500 . ? C11 C12 1.492(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.496(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.391(4) . ? C15 C16 1.364(4) . ? C15 H15 0.9500 . ? C16 C17 1.385(5) . ? C16 H16 0.9500 . ? C17 C18 1.381(4) . ? C17 H17 0.9500 . ? C18 C19 1.482(4) . ? C19 C20 1.382(4) . ? C20 C21 1.381(5) . ? C20 H20 0.9500 . ? C21 C22 1.363(5) . ? C21 H21 0.9500 . ? C22 C23 1.401(4) . ? C22 H22 0.9500 . ? C23 C24 1.490(5) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.491(4) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.395(4) . ? C27 C28 1.371(5) . ? C27 H27 0.9500 . ? C28 C29 1.379(5) . ? C28 H28 0.9500 . ? C29 C30 1.391(4) . ? C29 H29 0.9500 . ? C30 C31 1.479(4) . ? C31 C32 1.384(4) . ? C32 C33 1.373(5) . ? C32 H32 0.9500 . ? C33 C34 1.368(5) . ? C33 H33 0.9500 . ? C34 C35 1.390(4) . ? C34 H34 0.9500 . ? C35 C36 1.493(4) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 C38 1.493(5) . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 C39 1.384(4) . ? C39 C40 1.364(5) . ? C39 H39 0.9500 . ? C40 C41 1.386(5) . ? C40 H40 0.9500 . ? C41 C42 1.386(4) . ? C41 H41 0.9500 . ? C42 C43 1.478(4) . ? C43 C44 1.392(4) . ? C44 C45 1.366(5) . ? C44 H44 0.9500 . ? C45 C46 1.369(5) . ? C45 H45 0.9500 . ? C46 C47 1.402(4) . ? C46 H46 0.9500 . ? C47 C48 1.486(4) . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? 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 N4 146.61(10) . . ? N2 Cu1 N3 103.96(12) . . ? N4 Cu1 N3 83.10(12) . . ? N2 Cu1 N1 83.56(11) . . ? N4 Cu1 N1 115.41(11) . . ? N3 Cu1 N1 133.60(10) . . ? N8 Cu2 N7 83.79(11) . . ? N8 Cu2 N6 146.99(10) . . ? N7 Cu2 N6 107.15(11) . . ? N8 Cu2 N5 112.44(11) . . ? N7 Cu2 N5 132.31(11) . . ? N6 Cu2 N5 83.57(12) . . ? O1 Cl1 O2 110.1(2) . . ? O1 Cl1 O3 109.28(19) . . ? O2 Cl1 O3 111.03(18) . . ? O1 Cl1 O4 110.4(2) . . ? O2 Cl1 O4 107.72(19) . . ? O3 Cl1 O4 108.22(18) . . ? O8 Cl2 O5 110.1(2) . . ? O8 Cl2 O7 109.6(2) . . ? O5 Cl2 O7 110.37(19) . . ? O8 Cl2 O6 108.9(2) . . ? O5 Cl2 O6 108.69(17) . . ? O7 Cl2 O6 109.17(18) . . ? O11 Cl3 O12 107.9(2) . . ? O11 Cl3 O10 108.6(2) . . ? O12 Cl3 O10 111.1(2) . . ? O11 Cl3 O9 109.2(2) . . ? O12 Cl3 O9 110.15(17) . . ? O10 Cl3 O9 109.86(18) . . ? O16 Cl4 O13 108.99(18) . . ? O16 Cl4 O14 109.16(19) . . ? O13 Cl4 O14 109.87(17) . . ? O16 Cl4 O15 109.63(18) . . ? O13 Cl4 O15 109.55(18) . . ? O14 Cl4 O15 109.62(16) . . ? C2 N1 C6 119.6(2) . . ? C2 N1 Cu1 128.71(18) . . ? C6 N1 Cu1 110.95(18) . . ? C7 N2 C11 120.9(2) . . ? C7 N2 Cu1 113.98(19) . . ? C11 N2 Cu1 124.78(19) . . ? C18 N3 C14 119.3(2) . . ? C18 N3 Cu1 113.09(18) . . ? C14 N3 Cu1 127.64(18) . . ? C23 N4 C19 119.5(2) . . ? C23 N4 Cu1 127.3(2) . . ? C19 N4 Cu1 112.46(18) . . ? C26 N5 C30 120.6(2) . . ? C26 N5 Cu2 126.5(2) . . ? C30 N5 Cu2 112.07(19) . . ? C35 N6 C31 120.0(3) . . ? C35 N6 Cu2 127.2(2) . . ? C31 N6 Cu2 112.26(19) . . ? C42 N7 C38 120.9(2) . . ? C42 N7 Cu2 112.85(18) . . ? C38 N7 Cu2 126.2(2) . . ? C47 N8 C43 119.8(2) . . ? C47 N8 Cu2 127.0(2) . . ? C43 N8 Cu2 112.16(17) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 120.6(3) . . ? N1 C2 C1 119.2(3) . . ? C3 C2 C1 120.2(3) . . ? C4 C3 C2 119.4(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 119.9(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 118.9(3) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? N1 C6 C5 121.5(3) . . ? N1 C6 C7 115.5(2) . . ? C5 C6 C7 123.0(3) . . ? N2 C7 C8 121.4(3) . . ? N2 C7 C6 115.4(2) . . ? C8 C7 C6 123.2(3) . . ? C7 C8 C9 118.2(3) . . ? C7 C8 H8 120.9 . . ? C9 C8 H8 120.9 . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.1(3) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? N2 C11 C10 119.4(3) . . ? N2 C11 C12 119.2(2) . . ? C10 C11 C12 121.4(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 C15 120.4(2) . . ? N3 C14 C13 119.2(2) . . ? C15 C14 C13 120.3(3) . . ? C16 C15 C14 120.2(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 119.3(3) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C18 C17 C16 118.8(3) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? N3 C18 C17 121.9(3) . . ? N3 C18 C19 114.9(2) . . ? C17 C18 C19 123.2(2) . . ? N4 C19 C20 121.9(3) . . ? N4 C19 C18 116.0(2) . . ? C20 C19 C18 122.1(3) . . ? C21 C20 C19 119.0(3) . . ? C21 C20 H20 120.5 . . ? C19 C20 H20 120.5 . . ? C22 C21 C20 119.1(3) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C21 C22 C23 120.8(3) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? N4 C23 C22 119.7(3) . . ? N4 C23 C24 120.3(3) . . ? C22 C23 C24 119.9(3) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N5 C26 C27 119.8(3) . . ? N5 C26 C25 119.2(3) . . ? C27 C26 C25 120.9(3) . . ? C28 C27 C26 119.9(3) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C29 119.9(3) . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? C28 C29 C30 118.4(3) . . ? C28 C29 H29 120.8 . . ? C30 C29 H29 120.8 . . ? N5 C30 C29 121.3(3) . . ? N5 C30 C31 115.6(2) . . ? C29 C30 C31 123.0(3) . . ? N6 C31 C32 121.0(3) . . ? N6 C31 C30 115.4(3) . . ? C32 C31 C30 123.6(3) . . ? C33 C32 C31 119.0(3) . . ? C33 C32 H32 120.5 . . ? C31 C32 H32 120.5 . . ? C34 C33 C32 119.9(3) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C33 C34 C35 119.8(3) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? N6 C35 C34 120.2(3) . . ? N6 C35 C36 119.3(3) . . ? C34 C35 C36 120.5(3) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C38 C37 H37A 109.5 . . ? C38 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C38 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? N7 C38 C39 119.6(3) . . ? N7 C38 C37 119.2(3) . . ? C39 C38 C37 121.2(3) . . ? C40 C39 C38 120.0(3) . . ? C40 C39 H39 120.0 . . ? C38 C39 H39 120.0 . . ? C39 C40 C41 120.3(3) . . ? C39 C40 H40 119.8 . . ? C41 C40 H40 119.8 . . ? C40 C41 C42 118.3(3) . . ? C40 C41 H41 120.8 . . ? C42 C41 H41 120.8 . . ? N7 C42 C41 120.7(3) . . ? N7 C42 C43 115.0(2) . . ? C41 C42 C43 124.4(3) . . ? N8 C43 C44 121.8(3) . . ? N8 C43 C42 115.5(2) . . ? C44 C43 C42 122.6(3) . . ? C45 C44 C43 118.3(3) . . ? C45 C44 H44 120.8 . . ? C43 C44 H44 120.8 . . ? C44 C45 C46 120.2(3) . . ? C44 C45 H45 119.9 . . ? C46 C45 H45 119.9 . . ? C45 C46 C47 120.4(3) . . ? C45 C46 H46 119.8 . . ? C47 C46 H46 119.8 . . ? N8 C47 C46 119.4(3) . . ? N8 C47 C48 119.8(3) . . ? C46 C47 C48 120.7(3) . . ? C47 C48 H48A 109.5 . . ? C47 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C47 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 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 Cu1 N1 C2 174.5(2) . . . . ? N4 Cu1 N1 C2 -34.2(3) . . . . ? N3 Cu1 N1 C2 71.4(3) . . . . ? N2 Cu1 N1 C6 4.75(17) . . . . ? N4 Cu1 N1 C6 155.99(17) . . . . ? N3 Cu1 N1 C6 -98.4(2) . . . . ? N4 Cu1 N2 C7 -128.0(2) . . . . ? N3 Cu1 N2 C7 133.21(19) . . . . ? N1 Cu1 N2 C7 -0.18(18) . . . . ? N4 Cu1 N2 C11 44.9(3) . . . . ? N3 Cu1 N2 C11 -53.9(2) . . . . ? N1 Cu1 N2 C11 172.7(2) . . . . ? N2 Cu1 N3 C18 142.53(18) . . . . ? N4 Cu1 N3 C18 -4.25(17) . . . . ? N1 Cu1 N3 C18 -123.04(18) . . . . ? N2 Cu1 N3 C14 -37.5(2) . . . . ? N4 Cu1 N3 C14 175.7(2) . . . . ? N1 Cu1 N3 C14 56.9(3) . . . . ? N2 Cu1 N4 C23 71.2(3) . . . . ? N3 Cu1 N4 C23 176.1(2) . . . . ? N1 Cu1 N4 C23 -48.5(3) . . . . ? N2 Cu1 N4 C19 -98.9(2) . . . . ? N3 Cu1 N4 C19 6.09(18) . . . . ? N1 Cu1 N4 C19 141.45(18) . . . . ? N8 Cu2 N5 C26 40.8(2) . . . . ? N7 Cu2 N5 C26 -61.8(3) . . . . ? N6 Cu2 N5 C26 -169.1(2) . . . . ? N8 Cu2 N5 C30 -149.34(17) . . . . ? N7 Cu2 N5 C30 108.1(2) . . . . ? N6 Cu2 N5 C30 0.71(18) . . . . ? N8 Cu2 N6 C35 -56.1(3) . . . . ? N7 Cu2 N6 C35 49.4(3) . . . . ? N5 Cu2 N6 C35 -178.2(2) . . . . ? N8 Cu2 N6 C31 115.4(2) . . . . ? N7 Cu2 N6 C31 -139.11(19) . . . . ? N5 Cu2 N6 C31 -6.73(19) . . . . ? N8 Cu2 N7 C42 5.07(17) . . . . ? N6 Cu2 N7 C42 -143.06(18) . . . . ? N5 Cu2 N7 C42 119.91(19) . . . . ? N8 Cu2 N7 C38 -172.3(2) . . . . ? N6 Cu2 N7 C38 39.6(2) . . . . ? N5 Cu2 N7 C38 -57.4(3) . . . . ? N7 Cu2 N8 C47 -176.0(2) . . . . ? N6 Cu2 N8 C47 -63.9(3) . . . . ? N5 Cu2 N8 C47 50.5(2) . . . . ? N7 Cu2 N8 C43 -7.64(17) . . . . ? N6 Cu2 N8 C43 104.5(2) . . . . ? N5 Cu2 N8 C43 -141.08(17) . . . . ? C6 N1 C2 C3 -2.4(4) . . . . ? Cu1 N1 C2 C3 -171.4(2) . . . . ? C6 N1 C2 C1 175.3(2) . . . . ? Cu1 N1 C2 C1 6.2(4) . . . . ? N1 C2 C3 C4 3.4(4) . . . . ? C1 C2 C3 C4 -174.2(3) . . . . ? C2 C3 C4 C5 -1.8(5) . . . . ? C3 C4 C5 C6 -0.8(5) . . . . ? C2 N1 C6 C5 -0.3(4) . . . . ? Cu1 N1 C6 C5 170.6(2) . . . . ? C2 N1 C6 C7 -179.0(2) . . . . ? Cu1 N1 C6 C7 -8.2(3) . . . . ? C4 C5 C6 N1 1.9(4) . . . . ? C4 C5 C6 C7 -179.4(3) . . . . ? C11 N2 C7 C8 2.0(4) . . . . ? Cu1 N2 C7 C8 175.2(2) . . . . ? C11 N2 C7 C6 -177.4(2) . . . . ? Cu1 N2 C7 C6 -4.2(3) . . . . ? N1 C6 C7 N2 8.5(3) . . . . ? C5 C6 C7 N2 -170.3(3) . . . . ? N1 C6 C7 C8 -170.9(2) . . . . ? C5 C6 C7 C8 10.3(4) . . . . ? N2 C7 C8 C9 0.0(4) . . . . ? C6 C7 C8 C9 179.3(3) . . . . ? C7 C8 C9 C10 -1.0(5) . . . . ? C8 C9 C10 C11 0.2(5) . . . . ? C7 N2 C11 C10 -2.8(4) . . . . ? Cu1 N2 C11 C10 -175.3(2) . . . . ? C7 N2 C11 C12 177.0(3) . . . . ? Cu1 N2 C11 C12 4.5(4) . . . . ? C9 C10 C11 N2 1.7(4) . . . . ? C9 C10 C11 C12 -178.1(3) . . . . ? C18 N3 C14 C15 -4.2(4) . . . . ? Cu1 N3 C14 C15 175.8(2) . . . . ? C18 N3 C14 C13 175.7(2) . . . . ? Cu1 N3 C14 C13 -4.3(4) . . . . ? N3 C14 C15 C16 2.6(4) . . . . ? C13 C14 C15 C16 -177.2(3) . . . . ? C14 C15 C16 C17 0.6(5) . . . . ? C15 C16 C17 C18 -2.2(4) . . . . ? C14 N3 C18 C17 2.6(4) . . . . ? Cu1 N3 C18 C17 -177.4(2) . . . . ? C14 N3 C18 C19 -178.2(2) . . . . ? Cu1 N3 C18 C19 1.7(3) . . . . ? C16 C17 C18 N3 0.6(4) . . . . ? C16 C17 C18 C19 -178.5(3) . . . . ? C23 N4 C19 C20 2.4(4) . . . . ? Cu1 N4 C19 C20 173.3(2) . . . . ? C23 N4 C19 C18 -177.8(2) . . . . ? Cu1 N4 C19 C18 -6.9(3) . . . . ? N3 C18 C19 N4 3.5(3) . . . . ? C17 C18 C19 N4 -177.4(2) . . . . ? N3 C18 C19 C20 -176.7(2) . . . . ? C17 C18 C19 C20 2.5(4) . . . . ? N4 C19 C20 C21 -2.0(4) . . . . ? C18 C19 C20 C21 178.1(3) . . . . ? C19 C20 C21 C22 0.3(4) . . . . ? C20 C21 C22 C23 1.1(5) . . . . ? C19 N4 C23 C22 -1.0(4) . . . . ? Cu1 N4 C23 C22 -170.4(2) . . . . ? C19 N4 C23 C24 178.6(3) . . . . ? Cu1 N4 C23 C24 9.1(4) . . . . ? C21 C22 C23 N4 -0.8(4) . . . . ? C21 C22 C23 C24 179.7(3) . . . . ? C30 N5 C26 C27 1.6(4) . . . . ? Cu2 N5 C26 C27 170.6(2) . . . . ? C30 N5 C26 C25 -176.8(2) . . . . ? Cu2 N5 C26 C25 -7.7(4) . . . . ? N5 C26 C27 C28 -1.5(4) . . . . ? C25 C26 C27 C28 176.9(3) . . . . ? C26 C27 C28 C29 0.5(5) . . . . ? C27 C28 C29 C30 0.4(4) . . . . ? C26 N5 C30 C29 -0.7(4) . . . . ? Cu2 N5 C30 C29 -171.2(2) . . . . ? C26 N5 C30 C31 175.6(2) . . . . ? Cu2 N5 C30 C31 5.1(3) . . . . ? C28 C29 C30 N5 -0.3(4) . . . . ? C28 C29 C30 C31 -176.3(3) . . . . ? C35 N6 C31 C32 1.7(4) . . . . ? Cu2 N6 C31 C32 -170.4(2) . . . . ? C35 N6 C31 C30 -176.6(2) . . . . ? Cu2 N6 C31 C30 11.2(3) . . . . ? N5 C30 C31 N6 -11.1(3) . . . . ? C29 C30 C31 N6 165.1(3) . . . . ? N5 C30 C31 C32 170.6(3) . . . . ? C29 C30 C31 C32 -13.2(4) . . . . ? N6 C31 C32 C33 -2.4(5) . . . . ? C30 C31 C32 C33 175.8(3) . . . . ? C31 C32 C33 C34 0.4(5) . . . . ? C32 C33 C34 C35 2.2(5) . . . . ? C31 N6 C35 C34 0.9(4) . . . . ? Cu2 N6 C35 C34 171.7(2) . . . . ? C31 N6 C35 C36 -178.3(3) . . . . ? Cu2 N6 C35 C36 -7.4(4) . . . . ? C33 C34 C35 N6 -2.8(5) . . . . ? C33 C34 C35 C36 176.3(3) . . . . ? C42 N7 C38 C39 6.0(4) . . . . ? Cu2 N7 C38 C39 -176.8(2) . . . . ? C42 N7 C38 C37 -173.7(3) . . . . ? Cu2 N7 C38 C37 3.5(4) . . . . ? N7 C38 C39 C40 -3.2(5) . . . . ? C37 C38 C39 C40 176.5(3) . . . . ? C38 C39 C40 C41 -1.6(5) . . . . ? C39 C40 C41 C42 3.6(5) . . . . ? C38 N7 C42 C41 -4.0(4) . . . . ? Cu2 N7 C42 C41 178.47(19) . . . . ? C38 N7 C42 C43 175.8(2) . . . . ? Cu2 N7 C42 C43 -1.7(3) . . . . ? C40 C41 C42 N7 -0.8(4) . . . . ? C40 C41 C42 C43 179.4(3) . . . . ? C47 N8 C43 C44 -0.2(4) . . . . ? Cu2 N8 C43 C44 -169.5(2) . . . . ? C47 N8 C43 C42 178.1(2) . . . . ? Cu2 N8 C43 C42 8.8(3) . . . . ? N7 C42 C43 N8 -4.8(3) . . . . ? C41 C42 C43 N8 175.0(2) . . . . ? N7 C42 C43 C44 173.5(2) . . . . ? C41 C42 C43 C44 -6.7(4) . . . . ? N8 C43 C44 C45 -0.3(4) . . . . ? C42 C43 C44 C45 -178.5(3) . . . . ? C43 C44 C45 C46 0.1(4) . . . . ? C44 C45 C46 C47 0.7(4) . . . . ? C43 N8 C47 C46 1.0(4) . . . . ? Cu2 N8 C47 C46 168.58(19) . . . . ? C43 N8 C47 C48 -178.8(2) . . . . ? Cu2 N8 C47 C48 -11.2(4) . . . . ? C45 C46 C47 N8 -1.2(4) . . . . ? C45 C46 C47 C48 178.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.895 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.895 _refine_diff_density_max 0.535 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.059 data_Cudmp2 _database_code_depnum_ccdc_archive 'CCDC 251497' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(2,9-dimethylphenanthroline)copper(II) perchlorate nitromethane solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 Cu N4 2+. 2(Cl O4 1-), 2(C H3 N O2)' _chemical_formula_sum 'C30 H30 Cl2 Cu N6 O12' _chemical_formula_weight 801.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 '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' O O 0.0106 0.0060 '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' 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.456(4) _cell_length_b 13.476(5) _cell_length_c 14.730(6) _cell_angle_alpha 102.72(3) _cell_angle_beta 91.32(3) _cell_angle_gamma 92.46(3) _cell_volume 1635.0(11) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 12053 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description prismatic _exptl_crystal_colour red_brown _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 822 _exptl_absorpt_coefficient_mu 0.906 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15010 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0846 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7210 _reflns_number_gt 5053 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'teXsan ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ORTEP _computing_publication_material SHELXL-97 _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^)+(0.1060P)^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 7210 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.1694 _refine_ls_wR_factor_gt 0.1584 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.80136(6) 0.15698(3) 0.26207(3) 0.03420(16) Uani 1 1 d . . . Cl1 Cl 0.75562(12) -0.37096(7) 0.14514(6) 0.0410(2) Uani 1 1 d . . . Cl2 Cl 0.36841(11) 0.15172(7) 0.32139(6) 0.0376(2) Uani 1 1 d . . . O1 O 0.7375(6) -0.2801(3) 0.2086(3) 0.0993(15) Uani 1 1 d . . . O2 O 0.8342(5) -0.3457(3) 0.0678(3) 0.0785(11) Uani 1 1 d . . . O3 O 0.8440(6) -0.4358(3) 0.1861(3) 0.1016(16) Uani 1 1 d . . . O4 O 0.6074(5) -0.4170(3) 0.1129(3) 0.0903(14) Uani 1 1 d . . . O5 O 0.2716(5) 0.0634(3) 0.3100(3) 0.0916(14) Uani 1 1 d . . . O6 O 0.5215(4) 0.1237(4) 0.2991(4) 0.113(2) Uani 1 1 d . . . O7 O 0.3202(4) 0.2114(3) 0.2588(3) 0.0685(10) Uani 1 1 d . . . O8 O 0.3570(9) 0.2045(4) 0.4125(3) 0.137(2) Uani 1 1 d . . . O9 O 0.5154(6) -0.4217(3) 0.4279(4) 0.1186(18) Uani 1 1 d . . . O10 O 0.3079(4) -0.3486(3) 0.4710(3) 0.0651(9) Uani 1 1 d . . . O11 O 1.7725(6) 0.2780(3) 0.8040(3) 0.0879(13) Uani 1 1 d . . . O12 O 1.7354(5) 0.4218(3) 0.7701(3) 0.0850(12) Uani 1 1 d . . . N1 N 0.9627(3) 0.2638(2) 0.32454(19) 0.0282(6) Uani 1 1 d . . . N2 N 0.8306(3) 0.1041(2) 0.37634(19) 0.0295(6) Uani 1 1 d . . . N3 N 0.8112(3) 0.04950(19) 0.13975(18) 0.0267(6) Uani 1 1 d . . . N4 N 0.6840(3) 0.2313(2) 0.18449(19) 0.0280(6) Uani 1 1 d . . . N5 N 0.4300(5) -0.3532(3) 0.4329(3) 0.0536(9) Uani 1 1 d . . . N6 N 1.7637(5) 0.3691(3) 0.8251(3) 0.0614(10) Uani 1 1 d . . . C1 C 1.0279(5) 0.3377(3) 0.1925(3) 0.0419(9) Uani 1 1 d . . . H1A H 1.0747 0.2761 0.1575 0.051 Uiso 1 1 calc R . . H1B H 1.0865 0.3980 0.1813 0.051 Uiso 1 1 calc R . . H1C H 0.9170 0.3384 0.1721 0.051 Uiso 1 1 calc R . . C2 C 1.0366(4) 0.3385(3) 0.2933(3) 0.0339(8) Uani 1 1 d . . . C3 C 1.1249(5) 0.4165(3) 0.3556(3) 0.0434(9) Uani 1 1 d . . . H3 H 1.1755 0.4702 0.3329 0.054 Uiso 1 1 calc R . . C4 C 1.1387(5) 0.4162(3) 0.4469(3) 0.0432(9) Uani 1 1 d . . . H4 H 1.1959 0.4704 0.4886 0.051 Uiso 1 1 calc R . . C5 C 1.0686(5) 0.3358(3) 0.4802(3) 0.0368(8) Uani 1 1 d . . . C6 C 0.9819(4) 0.2608(2) 0.4155(2) 0.0293(7) Uani 1 1 d . . . C7 C 0.9111(4) 0.1752(3) 0.4432(2) 0.0301(7) Uani 1 1 d . . . C8 C 0.9252(5) 0.1682(3) 0.5359(2) 0.0365(8) Uani 1 1 d . . . C9 C 0.8502(5) 0.0828(3) 0.5592(3) 0.0425(9) Uani 1 1 d . . . H9 H 0.8558 0.0744 0.6216 0.052 Uiso 1 1 calc R . . C10 C 0.7695(5) 0.0122(3) 0.4921(3) 0.0425(9) Uani 1 1 d . . . H10 H 0.7187 -0.0456 0.5080 0.051 Uiso 1 1 calc R . . C11 C 0.7603(4) 0.0235(2) 0.3998(2) 0.0331(8) Uani 1 1 d . . . C12 C 0.6676(5) -0.0549(3) 0.3287(3) 0.0415(9) Uani 1 1 d . . . H12A H 0.7371 -0.0851 0.2788 0.052 Uiso 1 1 calc R . . H12B H 0.5808 -0.0229 0.3027 0.052 Uiso 1 1 calc R . . H12C H 0.6241 -0.1083 0.3581 0.052 Uiso 1 1 calc R . . C13 C 1.0789(5) 0.3273(3) 0.5744(3) 0.0459(10) Uani 1 1 d . . . H13 H 1.1350 0.3791 0.6192 0.054 Uiso 1 1 calc R . . C14 C 1.0103(5) 0.2470(3) 0.6012(3) 0.0458(10) Uani 1 1 d . . . H14 H 1.0188 0.2428 0.6646 0.054 Uiso 1 1 calc R . . C15 C 0.9802(4) -0.0710(3) 0.1898(3) 0.0366(8) Uani 1 1 d . . . H15A H 1.0234 -0.1370 0.1633 0.045 Uiso 1 1 calc R . . H15B H 0.9154 -0.0768 0.2429 0.045 Uiso 1 1 calc R . . H15C H 1.0673 -0.0201 0.2107 0.045 Uiso 1 1 calc R . . C16 C 0.8813(4) -0.0393(2) 0.1184(2) 0.0296(7) Uani 1 1 d . . . C17 C 0.8648(5) -0.1002(3) 0.0281(3) 0.0381(8) Uani 1 1 d . . . H17 H 0.9137 -0.1637 0.0144 0.046 Uiso 1 1 calc R . . C18 C 0.7809(5) -0.0708(3) -0.0400(3) 0.0404(9) Uani 1 1 d . . . H18 H 0.7705 -0.1133 -0.1008 0.048 Uiso 1 1 calc R . . C19 C 0.7093(4) 0.0236(3) -0.0198(2) 0.0340(8) Uani 1 1 d . . . C20 C 0.7281(4) 0.0806(2) 0.0709(2) 0.0282(7) Uani 1 1 d . . . C21 C 0.6592(4) 0.1773(2) 0.0951(2) 0.0274(7) Uani 1 1 d . . . C22 C 0.5701(4) 0.2125(3) 0.0293(3) 0.0365(8) Uani 1 1 d . . . C23 C 0.5018(5) 0.3074(3) 0.0589(3) 0.0440(10) Uani 1 1 d . . . H23 H 0.4395 0.3345 0.0164 0.053 Uiso 1 1 calc R . . C24 C 0.5256(5) 0.3594(3) 0.1478(3) 0.0438(9) Uani 1 1 d . . . H24 H 0.4804 0.4236 0.1678 0.053 Uiso 1 1 calc R . . C25 C 0.6164(4) 0.3196(3) 0.2111(3) 0.0355(8) Uani 1 1 d . . . C26 C 0.6379(5) 0.3777(3) 0.3090(3) 0.0469(10) Uani 1 1 d . . . H26A H 0.5809 0.4407 0.3172 0.057 Uiso 1 1 calc R . . H26B H 0.7508 0.3944 0.3236 0.057 Uiso 1 1 calc R . . H26C H 0.5960 0.3363 0.3509 0.057 Uiso 1 1 calc R . . C27 C 0.6197(5) 0.0619(3) -0.0866(3) 0.0430(9) Uani 1 1 d . . . H27 H 0.6077 0.0232 -0.1488 0.052 Uiso 1 1 calc R . . C28 C 0.5522(5) 0.1517(3) -0.0631(3) 0.0416(9) Uani 1 1 d . . . H28 H 0.4915 0.1752 -0.1085 0.051 Uiso 1 1 calc R . . C29 C 0.4844(7) -0.2684(4) 0.3913(4) 0.0742(15) Uani 1 1 d . . . H29A H 0.5845 -0.2379 0.4220 0.093 Uiso 1 1 calc R . . H29B H 0.4046 -0.2168 0.3996 0.093 Uiso 1 1 calc R . . H29C H 0.5002 -0.2939 0.3247 0.093 Uiso 1 1 calc R . . C30 C 1.7909(6) 0.4196(4) 0.9210(4) 0.0679(14) Uani 1 1 d . . . H30A H 1.8824 0.4679 0.9266 0.082 Uiso 1 1 calc R . . H30B H 1.8117 0.3690 0.9579 0.082 Uiso 1 1 calc R . . H30C H 1.6971 0.4563 0.9439 0.082 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0548(3) 0.0207(2) 0.0261(2) 0.00511(16) -0.01075(19) -0.00158(18) Cl1 0.0497(6) 0.0338(4) 0.0368(5) 0.0033(4) -0.0104(4) 0.0035(4) Cl2 0.0351(5) 0.0427(5) 0.0314(4) 0.0012(4) 0.0011(4) -0.0034(4) O1 0.136(4) 0.062(2) 0.080(3) -0.026(2) 0.008(3) 0.006(3) O2 0.080(3) 0.092(3) 0.069(2) 0.026(2) 0.013(2) 0.008(2) O3 0.109(4) 0.095(3) 0.117(4) 0.054(3) -0.022(3) 0.033(3) O4 0.087(3) 0.088(3) 0.103(3) 0.050(2) -0.044(3) -0.042(2) O5 0.104(3) 0.099(3) 0.068(2) 0.023(2) -0.003(2) -0.062(3) O6 0.041(2) 0.125(4) 0.221(6) 0.132(4) 0.036(3) 0.025(2) O7 0.053(2) 0.086(2) 0.076(2) 0.036(2) 0.0021(17) 0.0183(18) O8 0.247(7) 0.106(4) 0.042(2) -0.019(2) -0.001(3) 0.001(4) O9 0.106(4) 0.061(2) 0.182(5) 0.006(3) 0.026(4) 0.032(3) O10 0.052(2) 0.072(2) 0.071(2) 0.0146(19) 0.0170(18) 0.0009(17) O11 0.100(3) 0.051(2) 0.110(3) 0.010(2) 0.019(3) 0.003(2) O12 0.107(3) 0.085(3) 0.073(3) 0.042(2) 0.005(2) -0.009(2) N1 0.0303(15) 0.0246(13) 0.0296(14) 0.0055(11) 0.0009(12) 0.0032(11) N2 0.0351(16) 0.0242(13) 0.0292(14) 0.0064(11) -0.0015(12) 0.0005(12) N3 0.0307(15) 0.0244(12) 0.0245(13) 0.0049(11) 0.0014(11) -0.0024(11) N4 0.0308(15) 0.0241(13) 0.0301(14) 0.0089(11) 0.0006(12) -0.0021(11) N5 0.053(2) 0.0424(19) 0.061(2) 0.0003(18) 0.0030(19) 0.0051(18) N6 0.065(3) 0.059(2) 0.064(3) 0.021(2) 0.013(2) 0.000(2) C1 0.044(2) 0.042(2) 0.044(2) 0.0172(17) 0.0056(18) 0.0005(17) C2 0.0344(19) 0.0299(16) 0.0378(19) 0.0071(15) 0.0047(15) 0.0061(15) C3 0.041(2) 0.0296(18) 0.059(3) 0.0091(18) 0.0044(19) -0.0020(16) C4 0.043(2) 0.0321(18) 0.048(2) -0.0039(17) -0.0025(18) -0.0045(17) C5 0.038(2) 0.0315(17) 0.0368(19) -0.0014(15) -0.0020(16) 0.0025(15) C6 0.0297(18) 0.0282(15) 0.0289(16) 0.0036(13) 0.0014(14) 0.0034(14) C7 0.0314(18) 0.0309(16) 0.0285(16) 0.0068(14) -0.0029(14) 0.0058(14) C8 0.038(2) 0.044(2) 0.0290(17) 0.0099(16) 0.0014(15) 0.0086(16) C9 0.049(2) 0.051(2) 0.0330(19) 0.0209(18) 0.0022(17) 0.0072(19) C10 0.047(2) 0.040(2) 0.047(2) 0.0226(18) 0.0083(18) 0.0019(17) C11 0.0348(19) 0.0275(16) 0.0390(19) 0.0109(15) 0.0037(15) 0.0047(14) C12 0.047(2) 0.0283(17) 0.049(2) 0.0066(16) 0.0067(18) -0.0008(16) C13 0.047(2) 0.048(2) 0.037(2) -0.0031(18) -0.0087(18) -0.0001(19) C14 0.049(2) 0.058(2) 0.0285(18) 0.0042(18) -0.0092(17) 0.007(2) C15 0.036(2) 0.0337(18) 0.041(2) 0.0099(16) 0.0063(16) 0.0064(15) C16 0.0279(17) 0.0248(15) 0.0356(18) 0.0059(14) 0.0083(14) -0.0027(13) C17 0.042(2) 0.0281(16) 0.040(2) -0.0026(15) 0.0119(17) -0.0041(15) C18 0.045(2) 0.0397(19) 0.0298(18) -0.0066(16) 0.0074(16) -0.0089(17) C19 0.0344(19) 0.0399(18) 0.0263(17) 0.0065(15) 0.0045(14) -0.0121(16) C20 0.0311(18) 0.0300(16) 0.0229(15) 0.0059(13) 0.0019(13) -0.0055(14) C21 0.0269(17) 0.0282(15) 0.0284(16) 0.0099(13) 0.0029(13) -0.0050(13) C22 0.035(2) 0.045(2) 0.0346(18) 0.0198(17) -0.0029(16) -0.0053(16) C23 0.040(2) 0.045(2) 0.056(2) 0.031(2) -0.0045(19) 0.0015(17) C24 0.041(2) 0.0358(19) 0.060(3) 0.0218(19) 0.0032(19) 0.0058(17) C25 0.0335(19) 0.0287(16) 0.045(2) 0.0105(15) 0.0036(16) -0.0037(15) C26 0.050(2) 0.0335(18) 0.052(2) -0.0032(17) 0.0027(19) 0.0091(18) C27 0.040(2) 0.064(3) 0.0253(17) 0.0119(18) -0.0026(16) -0.0103(19) C28 0.039(2) 0.059(2) 0.0314(18) 0.0221(18) -0.0059(16) -0.0056(18) C29 0.073(4) 0.079(4) 0.074(4) 0.029(3) 0.005(3) -0.020(3) C30 0.059(3) 0.084(4) 0.061(3) 0.014(3) 0.008(2) 0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N4 1.957(3) . ? Cu N2 1.982(3) . ? Cu N1 1.993(3) . ? Cu N3 2.054(3) . ? Cl1 O1 1.384(4) . ? Cl1 O3 1.398(4) . ? Cl1 O4 1.399(4) . ? Cl1 O2 1.429(4) . ? Cl2 O8 1.381(4) . ? Cl2 O6 1.390(4) . ? Cl2 O5 1.391(4) . ? Cl2 O7 1.414(3) . ? O9 N5 1.187(5) . ? O10 N5 1.184(5) . ? O11 N6 1.205(5) . ? O12 N6 1.215(5) . ? N1 C2 1.333(5) . ? N1 C6 1.356(4) . ? N2 C11 1.332(4) . ? N2 C7 1.360(4) . ? N3 C16 1.337(4) . ? N3 C20 1.370(4) . ? N4 C25 1.327(4) . ? N4 C21 1.363(4) . ? N5 C29 1.473(6) . ? N6 C30 1.435(6) . ? C1 C2 1.483(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.407(5) . ? C3 C4 1.349(6) . ? C3 H3 0.9500 . ? C4 C5 1.399(6) . ? C4 H4 0.9500 . ? C5 C6 1.395(5) . ? C5 C13 1.419(5) . ? C6 C7 1.419(5) . ? C7 C8 1.393(5) . ? C8 C9 1.402(6) . ? C8 C14 1.422(5) . ? C9 C10 1.359(6) . ? C9 H9 0.9500 . ? C10 C11 1.402(5) . ? C10 H10 0.9500 . ? C11 C12 1.494(5) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.344(6) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.475(5) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.400(5) . ? C17 C18 1.355(5) . ? C17 H17 0.9500 . ? C18 C19 1.407(5) . ? C18 H18 0.9500 . ? C19 C20 1.388(5) . ? C19 C27 1.426(5) . ? C20 C21 1.427(5) . ? C21 C22 1.390(5) . ? C22 C23 1.410(6) . ? C22 C28 1.426(5) . ? C23 C24 1.349(6) . ? C23 H23 0.9500 . ? C24 C25 1.404(5) . ? C24 H24 0.9500 . ? C25 C26 1.485(5) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.339(6) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? 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 N4 Cu N2 152.16(13) . . ? N4 Cu N1 101.02(11) . . ? N2 Cu N1 83.62(12) . . ? N4 Cu N3 83.50(11) . . ? N2 Cu N3 114.69(11) . . ? N1 Cu N3 130.00(12) . . ? O1 Cl1 O3 110.0(3) . . ? O1 Cl1 O4 110.2(3) . . ? O3 Cl1 O4 110.7(3) . . ? O1 Cl1 O2 106.6(3) . . ? O3 Cl1 O2 111.4(3) . . ? O4 Cl1 O2 107.9(2) . . ? O8 Cl2 O6 113.1(4) . . ? O8 Cl2 O5 107.2(3) . . ? O6 Cl2 O5 108.2(3) . . ? O8 Cl2 O7 110.8(3) . . ? O6 Cl2 O7 107.0(2) . . ? O5 Cl2 O7 110.6(2) . . ? C2 N1 C6 119.1(3) . . ? C2 N1 Cu 130.5(2) . . ? C6 N1 Cu 110.1(2) . . ? C11 N2 C7 119.1(3) . . ? C11 N2 Cu 129.6(2) . . ? C7 N2 Cu 109.9(2) . . ? C16 N3 C20 118.5(3) . . ? C16 N3 Cu 132.1(2) . . ? C20 N3 Cu 109.4(2) . . ? C25 N4 C21 119.0(3) . . ? C25 N4 Cu 127.9(2) . . ? C21 N4 Cu 112.8(2) . . ? O10 N5 O9 123.9(5) . . ? O10 N5 C29 119.2(4) . . ? O9 N5 C29 116.9(5) . . ? O11 N6 O12 124.3(5) . . ? O11 N6 C30 118.3(5) . . ? O12 N6 C30 117.4(5) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 120.1(3) . . ? N1 C2 C1 119.6(3) . . ? C3 C2 C1 120.2(3) . . ? C4 C3 C2 120.9(4) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.8(4) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 116.8(3) . . ? C6 C5 C13 119.0(4) . . ? C4 C5 C13 124.2(4) . . ? N1 C6 C5 123.1(3) . . ? N1 C6 C7 116.7(3) . . ? C5 C6 C7 120.2(3) . . ? N2 C7 C8 123.3(3) . . ? N2 C7 C6 117.2(3) . . ? C8 C7 C6 119.4(3) . . ? C7 C8 C9 116.7(3) . . ? C7 C8 C14 119.3(4) . . ? C9 C8 C14 123.9(3) . . ? C10 C9 C8 119.6(3) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 120.9(4) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? N2 C11 C10 120.3(3) . . ? N2 C11 C12 120.5(3) . . ? C10 C11 C12 119.1(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C5 120.9(4) . . ? C14 C13 H13 119.5 . . ? C5 C13 H13 119.5 . . ? C13 C14 C8 121.0(4) . . ? C13 C14 H14 119.5 . . ? C8 C14 H14 119.5 . . ? C16 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C16 C17 120.2(3) . . ? N3 C16 C15 119.4(3) . . ? C17 C16 C15 120.4(3) . . ? C18 C17 C16 121.7(3) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C17 C18 C19 119.2(3) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C20 C19 C18 116.8(3) . . ? C20 C19 C27 119.5(4) . . ? C18 C19 C27 123.6(3) . . ? N3 C20 C19 123.6(3) . . ? N3 C20 C21 117.2(3) . . ? C19 C20 C21 119.2(3) . . ? N4 C21 C22 122.7(3) . . ? N4 C21 C20 117.0(3) . . ? C22 C21 C20 120.3(3) . . ? C21 C22 C23 117.2(3) . . ? C21 C22 C28 119.0(3) . . ? C23 C22 C28 123.8(3) . . ? C24 C23 C22 119.5(3) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C23 C24 C25 120.6(4) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? N4 C25 C24 121.0(4) . . ? N4 C25 C26 119.7(3) . . ? C24 C25 C26 119.4(3) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 C19 121.0(4) . . ? C28 C27 H27 119.5 . . ? C19 C27 H27 119.5 . . ? C27 C28 C22 120.8(3) . . ? C27 C28 H28 119.6 . . ? C22 C28 H28 119.6 . . ? N5 C29 H29A 109.5 . . ? N5 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? N5 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N6 C30 H30A 109.5 . . ? N6 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? N6 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 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 N4 Cu N1 C2 -34.2(3) . . . . ? N2 Cu N1 C2 173.6(3) . . . . ? N3 Cu N1 C2 56.6(3) . . . . ? N4 Cu N1 C6 138.7(2) . . . . ? N2 Cu N1 C6 -13.5(2) . . . . ? N3 Cu N1 C6 -130.5(2) . . . . ? N4 Cu N2 C11 77.8(4) . . . . ? N1 Cu N2 C11 179.4(3) . . . . ? N3 Cu N2 C11 -49.3(3) . . . . ? N4 Cu N2 C7 -88.1(3) . . . . ? N1 Cu N2 C7 13.4(2) . . . . ? N3 Cu N2 C7 144.8(2) . . . . ? N4 Cu N3 C16 176.8(3) . . . . ? N2 Cu N3 C16 -25.2(3) . . . . ? N1 Cu N3 C16 77.9(3) . . . . ? N4 Cu N3 C20 -2.9(2) . . . . ? N2 Cu N3 C20 155.1(2) . . . . ? N1 Cu N3 C20 -101.8(2) . . . . ? N2 Cu N4 C25 43.3(4) . . . . ? N1 Cu N4 C25 -54.0(3) . . . . ? N3 Cu N4 C25 176.5(3) . . . . ? N2 Cu N4 C21 -129.7(3) . . . . ? N1 Cu N4 C21 133.0(2) . . . . ? N3 Cu N4 C21 3.4(2) . . . . ? C6 N1 C2 C3 -4.0(5) . . . . ? Cu N1 C2 C3 168.3(3) . . . . ? C6 N1 C2 C1 174.7(3) . . . . ? Cu N1 C2 C1 -13.0(5) . . . . ? N1 C2 C3 C4 1.2(6) . . . . ? C1 C2 C3 C4 -177.5(4) . . . . ? C2 C3 C4 C5 2.0(6) . . . . ? C3 C4 C5 C6 -2.1(6) . . . . ? C3 C4 C5 C13 178.7(4) . . . . ? C2 N1 C6 C5 3.9(5) . . . . ? Cu N1 C6 C5 -169.9(3) . . . . ? C2 N1 C6 C7 -175.0(3) . . . . ? Cu N1 C6 C7 11.2(4) . . . . ? C4 C5 C6 N1 -0.8(5) . . . . ? C13 C5 C6 N1 178.5(3) . . . . ? C4 C5 C6 C7 178.1(3) . . . . ? C13 C5 C6 C7 -2.7(5) . . . . ? C11 N2 C7 C8 0.4(5) . . . . ? Cu N2 C7 C8 168.1(3) . . . . ? C11 N2 C7 C6 -178.9(3) . . . . ? Cu N2 C7 C6 -11.3(4) . . . . ? N1 C6 C7 N2 0.0(5) . . . . ? C5 C6 C7 N2 -178.9(3) . . . . ? N1 C6 C7 C8 -179.3(3) . . . . ? C5 C6 C7 C8 1.7(5) . . . . ? N2 C7 C8 C9 -0.5(5) . . . . ? C6 C7 C8 C9 178.8(3) . . . . ? N2 C7 C8 C14 -179.3(3) . . . . ? C6 C7 C8 C14 0.0(5) . . . . ? C7 C8 C9 C10 0.2(6) . . . . ? C14 C8 C9 C10 179.0(4) . . . . ? C8 C9 C10 C11 0.0(6) . . . . ? C7 N2 C11 C10 -0.1(5) . . . . ? Cu N2 C11 C10 -165.0(3) . . . . ? C7 N2 C11 C12 178.5(3) . . . . ? Cu N2 C11 C12 13.7(5) . . . . ? C9 C10 C11 N2 -0.1(6) . . . . ? C9 C10 C11 C12 -178.8(4) . . . . ? C6 C5 C13 C14 1.8(6) . . . . ? C4 C5 C13 C14 -179.0(4) . . . . ? C5 C13 C14 C8 -0.1(6) . . . . ? C7 C8 C14 C13 -0.9(6) . . . . ? C9 C8 C14 C13 -179.6(4) . . . . ? C20 N3 C16 C17 -2.2(5) . . . . ? Cu N3 C16 C17 178.1(3) . . . . ? C20 N3 C16 C15 175.9(3) . . . . ? Cu N3 C16 C15 -3.7(5) . . . . ? N3 C16 C17 C18 1.2(6) . . . . ? C15 C16 C17 C18 -176.9(4) . . . . ? C16 C17 C18 C19 0.4(6) . . . . ? C17 C18 C19 C20 -0.9(5) . . . . ? C17 C18 C19 C27 179.5(4) . . . . ? C16 N3 C20 C19 1.7(5) . . . . ? Cu N3 C20 C19 -178.6(3) . . . . ? C16 N3 C20 C21 -177.9(3) . . . . ? Cu N3 C20 C21 1.9(4) . . . . ? C18 C19 C20 N3 -0.1(5) . . . . ? C27 C19 C20 N3 179.5(3) . . . . ? C18 C19 C20 C21 179.4(3) . . . . ? C27 C19 C20 C21 -0.9(5) . . . . ? C25 N4 C21 C22 2.2(5) . . . . ? Cu N4 C21 C22 175.9(3) . . . . ? C25 N4 C21 C20 -177.2(3) . . . . ? Cu N4 C21 C20 -3.4(4) . . . . ? N3 C20 C21 N4 0.9(5) . . . . ? C19 C20 C21 N4 -178.6(3) . . . . ? N3 C20 C21 C22 -178.4(3) . . . . ? C19 C20 C21 C22 2.0(5) . . . . ? N4 C21 C22 C23 -1.1(5) . . . . ? C20 C21 C22 C23 178.2(3) . . . . ? N4 C21 C22 C28 179.1(3) . . . . ? C20 C21 C22 C28 -1.6(5) . . . . ? C21 C22 C23 C24 0.3(6) . . . . ? C28 C22 C23 C24 -179.9(4) . . . . ? C22 C23 C24 C25 -0.5(6) . . . . ? C21 N4 C25 C24 -2.4(5) . . . . ? Cu N4 C25 C24 -175.0(3) . . . . ? C21 N4 C25 C26 178.0(3) . . . . ? Cu N4 C25 C26 5.3(5) . . . . ? C23 C24 C25 N4 1.6(6) . . . . ? C23 C24 C25 C26 -178.8(4) . . . . ? C20 C19 C27 C28 -0.6(6) . . . . ? C18 C19 C27 C28 179.0(4) . . . . ? C19 C27 C28 C22 1.0(6) . . . . ? C21 C22 C28 C27 0.1(6) . . . . ? C23 C22 C28 C27 -179.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.774 _refine_diff_density_min -0.516 _refine_diff_density_rms 0.104 data_Cu(I)dmbp200K _database_code_depnum_ccdc_archive 'CCDC 251498' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(6,6'-dimethyl-2,2'-bipyridine)copper(I) perchlorate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 Cu N4 1+, Cl O4 1-' _chemical_formula_sum 'C24 H24 Cl Cu N4 O4' _chemical_formula_weight 531.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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 1 21/a 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 8.833(5) _cell_length_b 21.684(12) _cell_length_c 12.384(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.68(4) _cell_angle_gamma 90.00 _cell_volume 2361(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 17609 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 1.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.535 _exptl_absorpt_correction_T_max 0.806 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis-rapid' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22552 _diffrn_reflns_av_R_equivalents 0.0939 _diffrn_reflns_av_sigmaI/netI 0.0770 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5403 _reflns_number_gt 3664 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction 'teXsan ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ORTEP _computing_publication_material SHELXL-97 _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^)+(0.0500P)^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 SHELXL _refine_ls_extinction_coef 0.0017(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5403 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.41388(4) 0.374085(14) 0.79051(3) 0.02935(11) Uani 1 1 d . . . Cl1 Cl 0.07495(9) 0.62974(3) 0.70247(6) 0.04196(18) Uani 1 1 d . . . O11 O -0.0803(4) 0.64977(17) 0.6879(3) 0.0975(11) Uani 1 1 d . . . O12 O 0.1671(3) 0.68283(12) 0.6925(2) 0.0705(8) Uani 1 1 d . . . O13 O 0.0999(5) 0.58887(14) 0.6187(3) 0.0971(12) Uani 1 1 d . . . O14 O 0.1018(5) 0.6029(2) 0.8050(3) 0.1211(15) Uani 1 1 d . . . N1 N 0.5239(3) 0.44327(9) 0.71748(17) 0.0268(5) Uani 1 1 d . . . N2 N 0.4851(2) 0.32560(9) 0.66567(17) 0.0260(4) Uani 1 1 d . . . N3 N 0.4262(3) 0.34794(9) 0.94842(18) 0.0269(5) Uani 1 1 d . . . N4 N 0.1961(2) 0.39554(9) 0.81949(18) 0.0286(5) Uani 1 1 d . . . C1 C 0.4642(4) 0.52056(14) 0.8488(3) 0.0497(9) Uani 1 1 d . . . H1A H 0.4798 0.5647 0.8627 0.061 Uiso 1 1 calc R . . H1B H 0.5108 0.4969 0.9109 0.061 Uiso 1 1 calc R . . H1C H 0.3550 0.5117 0.8384 0.061 Uiso 1 1 calc R . . C2 C 0.5363(3) 0.50272(12) 0.7487(2) 0.0321(6) Uani 1 1 d . . . C3 C 0.6135(4) 0.54526(12) 0.6907(2) 0.0369(7) Uani 1 1 d . . . H3 H 0.6218 0.5870 0.7141 0.044 Uiso 1 1 calc R . . C4 C 0.6777(4) 0.52680(13) 0.5995(2) 0.0382(7) Uani 1 1 d . . . H4 H 0.7316 0.5555 0.5597 0.045 Uiso 1 1 calc R . . C5 C 0.6630(3) 0.46602(12) 0.5662(2) 0.0321(6) Uani 1 1 d . . . H5 H 0.7063 0.4523 0.5032 0.038 Uiso 1 1 calc R . . C6 C 0.5840(3) 0.42546(11) 0.6264(2) 0.0253(5) Uani 1 1 d . . . C7 C 0.5597(3) 0.35987(11) 0.5960(2) 0.0265(5) Uani 1 1 d . . . C8 C 0.6097(3) 0.33475(13) 0.5031(2) 0.0355(6) Uani 1 1 d . . . H8 H 0.6620 0.3595 0.4556 0.042 Uiso 1 1 calc R . . C9 C 0.5825(4) 0.27327(14) 0.4806(3) 0.0429(7) Uani 1 1 d . . . H9 H 0.6146 0.2552 0.4168 0.050 Uiso 1 1 calc R . . C10 C 0.5079(4) 0.23833(13) 0.5517(3) 0.0400(7) Uani 1 1 d . . . H10 H 0.4887 0.1958 0.5375 0.047 Uiso 1 1 calc R . . C11 C 0.4611(3) 0.26543(12) 0.6442(2) 0.0304(6) Uani 1 1 d . . . C12 C 0.3826(4) 0.22962(13) 0.7254(3) 0.0398(7) Uani 1 1 d . . . H12A H 0.3708 0.1866 0.7015 0.048 Uiso 1 1 calc R . . H12B H 0.2821 0.2476 0.7319 0.048 Uiso 1 1 calc R . . H12C H 0.4433 0.2311 0.7960 0.048 Uiso 1 1 calc R . . C13 C 0.6868(4) 0.31325(16) 0.9556(3) 0.0491(8) Uani 1 1 d . . . H13A H 0.7628 0.2927 1.0063 0.058 Uiso 1 1 calc R . . H13B H 0.7247 0.3540 0.9370 0.058 Uiso 1 1 calc R . . H13C H 0.6679 0.2884 0.8895 0.058 Uiso 1 1 calc R . . C14 C 0.5430(3) 0.32039(12) 1.0071(2) 0.0339(6) Uani 1 1 d . . . C15 C 0.5291(4) 0.29964(13) 1.1122(2) 0.0438(8) Uani 1 1 d . . . H15 H 0.6133 0.2808 1.1533 0.052 Uiso 1 1 calc R . . C16 C 0.3935(4) 0.30650(13) 1.1560(2) 0.0449(8) Uani 1 1 d . . . H16 H 0.3822 0.2914 1.2267 0.052 Uiso 1 1 calc R . . C17 C 0.2739(4) 0.33535(13) 1.0969(2) 0.0381(7) Uani 1 1 d . . . H17 H 0.1800 0.3413 1.1267 0.045 Uiso 1 1 calc R . . C18 C 0.2930(3) 0.35565(11) 0.9929(2) 0.0287(6) Uani 1 1 d . . . C19 C 0.1709(3) 0.38823(11) 0.9249(2) 0.0308(6) Uani 1 1 d . . . C20 C 0.0419(4) 0.41146(15) 0.9643(3) 0.0477(8) Uani 1 1 d . . . H20 H 0.0256 0.4056 1.0382 0.056 Uiso 1 1 calc R . . C21 C -0.0627(4) 0.44305(18) 0.8964(4) 0.0584(10) Uani 1 1 d . . . H21 H -0.1516 0.4595 0.9228 0.070 Uiso 1 1 calc R . . C22 C -0.0372(4) 0.45056(16) 0.7901(3) 0.0511(9) Uani 1 1 d . . . H22 H -0.1085 0.4724 0.7419 0.062 Uiso 1 1 calc R . . C23 C 0.0934(3) 0.42616(12) 0.7528(3) 0.0367(6) Uani 1 1 d . . . C24 C 0.1254(4) 0.43350(16) 0.6375(3) 0.0487(8) Uani 1 1 d . . . H24A H 0.1348 0.3927 0.6046 0.058 Uiso 1 1 calc R . . H24B H 0.2206 0.4564 0.6346 0.058 Uiso 1 1 calc R . . H24C H 0.0418 0.4562 0.5975 0.058 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 0.03487(18) 0.03060(16) 0.02461(16) 0.00193(14) 0.01308(13) 0.00063(15) Cl1 0.0563(4) 0.0410(3) 0.0318(3) 0.0003(3) 0.0205(3) -0.0013(3) O11 0.0624(19) 0.117(3) 0.119(3) 0.030(2) 0.037(2) 0.0063(18) O12 0.081(2) 0.0640(16) 0.0692(19) -0.0169(14) 0.0206(16) -0.0243(15) O13 0.147(3) 0.0662(17) 0.091(2) -0.0388(16) 0.075(2) -0.0302(19) O14 0.147(4) 0.164(4) 0.058(2) 0.058(2) 0.038(2) 0.034(3) N1 0.0340(12) 0.0258(10) 0.0215(10) 0.0000(8) 0.0071(9) -0.0010(9) N2 0.0274(11) 0.0274(10) 0.0243(11) -0.0012(8) 0.0079(9) -0.0007(9) N3 0.0333(12) 0.0230(9) 0.0249(11) 0.0004(8) 0.0057(10) -0.0011(9) N4 0.0282(11) 0.0282(10) 0.0303(11) -0.0012(9) 0.0075(10) -0.0017(9) C1 0.072(2) 0.0378(15) 0.0436(19) -0.0112(14) 0.0264(18) -0.0109(15) C2 0.0419(15) 0.0291(13) 0.0257(13) -0.0016(10) 0.0056(12) -0.0015(11) C3 0.0509(18) 0.0259(12) 0.0336(15) 0.0001(11) 0.0024(14) -0.0060(12) C4 0.0491(18) 0.0349(14) 0.0309(15) 0.0080(12) 0.0054(14) -0.0107(13) C5 0.0384(15) 0.0356(13) 0.0238(13) 0.0009(11) 0.0102(12) -0.0037(12) C6 0.0289(12) 0.0262(12) 0.0207(11) 0.0018(9) 0.0029(10) 0.0001(10) C7 0.0274(12) 0.0302(13) 0.0220(12) 0.0005(10) 0.0035(11) -0.0002(10) C8 0.0407(16) 0.0382(14) 0.0296(14) -0.0029(11) 0.0137(13) -0.0027(12) C9 0.0523(19) 0.0451(16) 0.0341(16) -0.0141(13) 0.0175(15) -0.0002(14) C10 0.0470(18) 0.0311(14) 0.0432(17) -0.0103(12) 0.0110(15) -0.0028(12) C11 0.0298(14) 0.0296(12) 0.0320(14) -0.0017(11) 0.0042(12) -0.0013(10) C12 0.0466(17) 0.0306(13) 0.0439(17) 0.0004(12) 0.0131(15) -0.0083(12) C13 0.0402(18) 0.0570(19) 0.050(2) 0.0105(16) 0.0042(16) 0.0101(15) C14 0.0441(16) 0.0266(12) 0.0306(14) -0.0001(11) 0.0025(13) 0.0011(12) C15 0.072(2) 0.0282(13) 0.0295(15) 0.0025(11) -0.0043(16) 0.0035(14) C16 0.081(2) 0.0315(14) 0.0237(14) 0.0011(11) 0.0131(16) -0.0088(15) C17 0.0542(18) 0.0364(14) 0.0264(14) -0.0024(11) 0.0173(14) -0.0129(13) C18 0.0385(14) 0.0235(11) 0.0255(13) -0.0040(10) 0.0109(12) -0.0074(10) C19 0.0324(14) 0.0292(13) 0.0328(14) -0.0041(10) 0.0129(12) -0.0054(10) C20 0.0438(18) 0.0555(18) 0.0478(19) -0.0087(15) 0.0245(16) -0.0016(15) C21 0.0330(17) 0.066(2) 0.078(3) -0.015(2) 0.0132(19) 0.0102(16) C22 0.0363(17) 0.0495(18) 0.066(2) -0.0065(17) -0.0040(18) 0.0096(14) C23 0.0382(16) 0.0300(13) 0.0412(16) -0.0006(12) 0.0000(14) -0.0010(12) C24 0.055(2) 0.0505(18) 0.0392(18) 0.0099(14) -0.0032(16) 0.0040(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 2.021(2) . ? Cu1 N3 2.029(2) . ? Cu1 N4 2.045(2) . ? Cu1 N1 2.047(2) . ? Cl1 O14 1.395(3) . ? Cl1 O13 1.399(3) . ? Cl1 O12 1.422(3) . ? Cl1 O11 1.433(3) . ? N1 C2 1.347(3) . ? N1 C6 1.349(3) . ? N2 C11 1.344(3) . ? N2 C7 1.358(3) . ? N3 C14 1.342(4) . ? N3 C18 1.358(4) . ? N4 C23 1.340(4) . ? N4 C19 1.355(3) . ? C1 C2 1.499(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.389(4) . ? C3 C4 1.373(4) . ? C3 H3 0.9500 . ? C4 C5 1.383(4) . ? C4 H4 0.9500 . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.482(3) . ? C7 C8 1.384(4) . ? C8 C9 1.378(4) . ? C8 H8 0.9500 . ? C9 C10 1.378(4) . ? C9 H9 0.9500 . ? C10 C11 1.386(4) . ? C10 H10 0.9500 . ? C11 C12 1.495(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.485(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.394(4) . ? C15 C16 1.371(5) . ? C15 H15 0.9500 . ? C16 C17 1.375(5) . ? C16 H16 0.9500 . ? C17 C18 1.387(4) . ? C17 H17 0.9500 . ? C18 C19 1.480(4) . ? C19 C20 1.379(4) . ? C20 C21 1.369(5) . ? C20 H20 0.9500 . ? C21 C22 1.368(5) . ? C21 H21 0.9500 . ? C22 C23 1.389(4) . ? C22 H22 0.9500 . ? C23 C24 1.492(5) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? 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 N3 126.94(9) . . ? N2 Cu1 N4 128.48(9) . . ? N3 Cu1 N4 81.72(10) . . ? N2 Cu1 N1 81.13(9) . . ? N3 Cu1 N1 130.42(9) . . ? N4 Cu1 N1 114.02(9) . . ? O14 Cl1 O13 112.7(3) . . ? O14 Cl1 O12 111.7(2) . . ? O13 Cl1 O12 108.34(18) . . ? O14 Cl1 O11 108.4(2) . . ? O13 Cl1 O11 108.5(3) . . ? O12 Cl1 O11 107.0(2) . . ? C2 N1 C6 119.1(2) . . ? C2 N1 Cu1 127.09(19) . . ? C6 N1 Cu1 113.75(16) . . ? C11 N2 C7 118.8(2) . . ? C11 N2 Cu1 126.97(18) . . ? C7 N2 Cu1 114.14(16) . . ? C14 N3 C18 119.1(2) . . ? C14 N3 Cu1 127.68(19) . . ? C18 N3 Cu1 112.98(18) . . ? C23 N4 C19 119.1(2) . . ? C23 N4 Cu1 126.5(2) . . ? C19 N4 Cu1 112.91(19) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 121.1(3) . . ? N1 C2 C1 117.1(2) . . ? C3 C2 C1 121.8(3) . . ? C4 C3 C2 119.7(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 119.3(3) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C4 C5 C6 118.8(3) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? N1 C6 C5 121.9(2) . . ? N1 C6 C7 115.4(2) . . ? C5 C6 C7 122.7(2) . . ? N2 C7 C8 121.9(2) . . ? N2 C7 C6 115.5(2) . . ? C8 C7 C6 122.6(2) . . ? C9 C8 C7 119.0(3) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C10 C9 C8 119.2(3) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C9 C10 C11 119.7(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? N2 C11 C10 121.4(2) . . ? N2 C11 C12 116.5(2) . . ? C10 C11 C12 122.1(2) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 C15 121.0(3) . . ? N3 C14 C13 117.3(3) . . ? C15 C14 C13 121.7(3) . . ? C16 C15 C14 119.7(3) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 119.6(3) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C16 C17 C18 118.8(3) . . ? C16 C17 H17 120.6 . . ? C18 C17 H17 120.6 . . ? N3 C18 C17 121.8(3) . . ? N3 C18 C19 116.1(2) . . ? C17 C18 C19 122.1(3) . . ? N4 C19 C20 121.2(3) . . ? N4 C19 C18 115.1(2) . . ? C20 C19 C18 123.7(3) . . ? C21 C20 C19 119.8(3) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C22 C21 C20 119.0(3) . . ? C22 C21 H21 120.5 . . ? C20 C21 H21 120.5 . . ? C21 C22 C23 119.7(3) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? N4 C23 C22 121.2(3) . . ? N4 C23 C24 117.5(3) . . ? C22 C23 C24 121.3(3) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 Cu1 N1 C2 178.9(2) . . . . ? N3 Cu1 N1 C2 -49.4(3) . . . . ? N4 Cu1 N1 C2 50.6(3) . . . . ? N2 Cu1 N1 C6 1.37(18) . . . . ? N3 Cu1 N1 C6 133.13(17) . . . . ? N4 Cu1 N1 C6 -126.94(18) . . . . ? N3 Cu1 N2 C11 45.3(3) . . . . ? N4 Cu1 N2 C11 -66.3(3) . . . . ? N1 Cu1 N2 C11 180.0(2) . . . . ? N3 Cu1 N2 C7 -137.40(17) . . . . ? N4 Cu1 N2 C7 111.05(18) . . . . ? N1 Cu1 N2 C7 -2.67(18) . . . . ? N2 Cu1 N3 C14 42.6(3) . . . . ? N4 Cu1 N3 C14 175.2(2) . . . . ? N1 Cu1 N3 C14 -70.2(2) . . . . ? N2 Cu1 N3 C18 -131.50(16) . . . . ? N4 Cu1 N3 C18 1.13(16) . . . . ? N1 Cu1 N3 C18 115.73(18) . . . . ? N2 Cu1 N4 C23 -57.2(3) . . . . ? N3 Cu1 N4 C23 171.5(2) . . . . ? N1 Cu1 N4 C23 40.8(2) . . . . ? N2 Cu1 N4 C19 136.97(17) . . . . ? N3 Cu1 N4 C19 5.66(17) . . . . ? N1 Cu1 N4 C19 -125.07(17) . . . . ? C6 N1 C2 C3 -2.0(4) . . . . ? Cu1 N1 C2 C3 -179.3(2) . . . . ? C6 N1 C2 C1 178.5(3) . . . . ? Cu1 N1 C2 C1 1.1(4) . . . . ? N1 C2 C3 C4 0.4(5) . . . . ? C1 C2 C3 C4 180.0(3) . . . . ? C2 C3 C4 C5 0.7(5) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C2 N1 C6 C5 2.4(4) . . . . ? Cu1 N1 C6 C5 -179.8(2) . . . . ? C2 N1 C6 C7 -177.7(2) . . . . ? Cu1 N1 C6 C7 0.1(3) . . . . ? C4 C5 C6 N1 -1.3(4) . . . . ? C4 C5 C6 C7 178.8(3) . . . . ? C11 N2 C7 C8 0.8(4) . . . . ? Cu1 N2 C7 C8 -176.8(2) . . . . ? C11 N2 C7 C6 -179.0(2) . . . . ? Cu1 N2 C7 C6 3.5(3) . . . . ? N1 C6 C7 N2 -2.3(3) . . . . ? C5 C6 C7 N2 177.6(2) . . . . ? N1 C6 C7 C8 177.9(2) . . . . ? C5 C6 C7 C8 -2.2(4) . . . . ? N2 C7 C8 C9 0.3(4) . . . . ? C6 C7 C8 C9 -180.0(3) . . . . ? C7 C8 C9 C10 -0.8(5) . . . . ? C8 C9 C10 C11 0.3(5) . . . . ? C7 N2 C11 C10 -1.4(4) . . . . ? Cu1 N2 C11 C10 175.9(2) . . . . ? C7 N2 C11 C12 178.3(2) . . . . ? Cu1 N2 C11 C12 -4.5(4) . . . . ? C9 C10 C11 N2 0.8(5) . . . . ? C9 C10 C11 C12 -178.8(3) . . . . ? C18 N3 C14 C15 0.2(4) . . . . ? Cu1 N3 C14 C15 -173.6(2) . . . . ? C18 N3 C14 C13 -179.6(2) . . . . ? Cu1 N3 C14 C13 6.6(4) . . . . ? N3 C14 C15 C16 1.0(4) . . . . ? C13 C14 C15 C16 -179.2(3) . . . . ? C14 C15 C16 C17 -1.8(4) . . . . ? C15 C16 C17 C18 1.4(4) . . . . ? C14 N3 C18 C17 -0.6(4) . . . . ? Cu1 N3 C18 C17 174.1(2) . . . . ? C14 N3 C18 C19 178.0(2) . . . . ? Cu1 N3 C18 C19 -7.3(3) . . . . ? C16 C17 C18 N3 -0.2(4) . . . . ? C16 C17 C18 C19 -178.7(2) . . . . ? C23 N4 C19 C20 0.2(4) . . . . ? Cu1 N4 C19 C20 167.3(2) . . . . ? C23 N4 C19 C18 -178.0(2) . . . . ? Cu1 N4 C19 C18 -11.0(3) . . . . ? N3 C18 C19 N4 12.5(3) . . . . ? C17 C18 C19 N4 -168.9(2) . . . . ? N3 C18 C19 C20 -165.8(3) . . . . ? C17 C18 C19 C20 12.8(4) . . . . ? N4 C19 C20 C21 -0.6(5) . . . . ? C18 C19 C20 C21 177.5(3) . . . . ? C19 C20 C21 C22 0.5(5) . . . . ? C20 C21 C22 C23 0.0(6) . . . . ? C19 N4 C23 C22 0.3(4) . . . . ? Cu1 N4 C23 C22 -164.8(2) . . . . ? C19 N4 C23 C24 179.7(3) . . . . ? Cu1 N4 C23 C24 14.7(4) . . . . ? C21 C22 C23 N4 -0.4(5) . . . . ? C21 C22 C23 C24 -179.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.406 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.075