# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1-CH3OH _audit_creation_method SHELXL-2013 _chemical_name_systematic ; bis(\m~2~-4-(E)-(4-chlorobenzylidene)amino-4H-1,2,4-triazole)-bis((E)-4-(chlor obenzylidene)amino-4H-1,2,4-triazole)-di-copper(i) diperchlorate methanol 5.24-solvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H28 Cl4 Cu2 N16, 2(Cl O4), 5.24(C H4 O)' _chemical_formula_sum 'C41.23 H48.96 Cl6 Cu2 N16 O13.22' _chemical_formula_weight 1320.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.955(2) _cell_length_b 18.182(3) _cell_length_c 22.181(3) _cell_angle_alpha 90 _cell_angle_beta 95.31(3) _cell_angle_gamma 90 _cell_volume 2792.9(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11139 _cell_measurement_theta_min 2.8973 _cell_measurement_theta_max 36.8768 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.570 _exptl_crystal_F_000 1348 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_absorpt_coefficient_mu 1.123 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 50448 _diffrn_reflns_av_unetI/netI 0.1429 _diffrn_reflns_av_R_equivalents 0.0875 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.902 _diffrn_reflns_theta_max 36.937 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.937 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.937 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.937 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 13242 _reflns_number_gt 5024 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) ; _computing_structure_solution ; SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.) ; _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0708P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 13242 _refine_ls_number_parameters 454 _refine_ls_number_restraints 248 _refine_ls_R_factor_all 0.1709 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1521 _refine_ls_wR_factor_gt 0.1287 _refine_ls_goodness_of_fit_ref 0.868 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0.004 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu -0.04075(4) 0.57272(2) 0.54951(2) 0.02990(9) Uani 1 1 d . . . . . Cl5 Cl 0.39002(9) 0.87992(4) 0.09805(3) 0.04143(18) Uani 1 1 d . . . . . Cl15 Cl -0.42196(9) 0.93459(4) 0.96036(3) 0.03748(16) Uani 1 1 d . . . . . N1 N 0.0777(3) 0.52908(12) 0.42783(9) 0.0291(5) Uani 1 1 d . . . . . N2 N 0.0683(3) 0.58637(12) 0.46907(9) 0.0288(5) Uani 1 1 d . . . . . N3 N 0.1472(3) 0.63142(12) 0.38339(9) 0.0290(5) Uani 1 1 d . . . . . N4 N 0.1933(3) 0.68729(12) 0.34380(9) 0.0310(5) Uani 1 1 d . . . . . N11 N -0.1116(3) 0.66548(13) 0.58373(9) 0.0342(5) Uani 1 1 d . . . . . N12 N -0.1341(5) 0.72878(16) 0.54924(11) 0.0577(8) Uani 1 1 d . . . . . N13 N -0.1920(3) 0.75405(14) 0.64229(10) 0.0387(6) Uani 1 1 d . . . . . N14 N -0.2387(3) 0.79965(14) 0.68985(10) 0.0406(6) Uani 1 1 d . . . . . C1 C 0.2025(4) 0.66702(16) 0.28855(11) 0.0328(6) Uani 1 1 d . . . . . H1A H 0.1798 0.6182 0.2775 0.039 Uiso 1 1 calc R U . . . C2 C 0.2490(3) 0.72111(16) 0.24294(10) 0.0317(6) Uani 1 1 d . . . . . C3 C 0.2832(4) 0.79517(16) 0.25690(11) 0.0366(6) Uani 1 1 d . . . . . H3A H 0.2753 0.8116 0.2963 0.044 Uiso 1 1 calc R U . . . C4 C 0.3285(4) 0.84428(17) 0.21285(12) 0.0399(6) Uani 1 1 d . . . . . H4A H 0.3520 0.8935 0.2222 0.048 Uiso 1 1 calc R U . . . C5 C 0.3381(4) 0.81860(16) 0.15447(11) 0.0344(6) Uani 1 1 d . . . . . C6 C 0.3044(4) 0.74581(17) 0.13910(11) 0.0370(6) Uani 1 1 d . . . . . H6A H 0.3111 0.7298 0.0995 0.044 Uiso 1 1 calc R U . . . C7 C 0.2602(4) 0.69696(17) 0.18398(12) 0.0370(6) Uani 1 1 d . . . . . H7A H 0.2379 0.6477 0.1745 0.044 Uiso 1 1 calc R U . . . C8 C 0.1262(4) 0.55787(15) 0.37672(11) 0.0314(6) Uani 1 1 d . . . . . H8A H 0.1432 0.5316 0.3416 0.038 Uiso 1 1 calc R U . . . C9 C 0.1110(4) 0.64638(15) 0.44142(11) 0.0305(5) Uani 1 1 d . . . . . H9A H 0.1160 0.6930 0.4588 0.037 Uiso 1 1 calc R U . . . C11 C -0.2453(4) 0.76810(18) 0.74068(12) 0.0394(7) Uani 1 1 d . . . . . H11A H -0.2213 0.7179 0.7444 0.047 Uiso 1 1 calc R U . . . C12 C -0.2910(4) 0.81096(17) 0.79361(12) 0.0372(7) Uani 1 1 d . . . . . C13 C -0.3296(4) 0.88553(17) 0.79040(12) 0.0402(7) Uani 1 1 d . . . . . H13A H -0.3284 0.9101 0.7536 0.048 Uiso 1 1 calc R U . . . C14 C -0.3700(4) 0.92373(17) 0.84156(12) 0.0393(6) Uani 1 1 d . . . . . H14A H -0.3960 0.9739 0.8395 0.047 Uiso 1 1 calc R U . . . C15 C -0.3715(3) 0.88680(17) 0.89568(11) 0.0349(6) Uani 1 1 d . . . . . C16 C -0.3338(4) 0.81290(18) 0.90051(13) 0.0418(7) Uani 1 1 d . . . . . H16A H -0.3348 0.7890 0.9375 0.050 Uiso 1 1 calc R U . . . C17 C -0.2938(4) 0.77437(19) 0.84862(12) 0.0416(7) Uani 1 1 d . . . . . H17A H -0.2690 0.7241 0.8509 0.050 Uiso 1 1 calc R U . . . C18 C -0.1482(4) 0.68142(16) 0.63915(12) 0.0342(6) Uani 1 1 d . . . . . H18A H -0.1447 0.6483 0.6712 0.041 Uiso 1 1 calc R U . . . C19 C -0.1818(6) 0.7803(2) 0.58618(13) 0.0621(10) Uani 1 1 d . . . . . H19A H -0.2056 0.8290 0.5750 0.075 Uiso 1 1 calc R U . . . Cl1 Cl 0.17317(14) 0.46034(5) 0.21734(4) 0.0577(2) Uani 1 1 d D . . . . O1 O 0.1078(7) 0.39353(18) 0.1900(2) 0.0623(16) Uani 0.530(6) 1 d D U P A 1 O2 O 0.0041(6) 0.4984(3) 0.2331(3) 0.111(3) Uani 0.530(6) 1 d D U P A 1 O3 O 0.2758(6) 0.4412(3) 0.27469(16) 0.0578(14) Uani 0.530(6) 1 d D U P A 1 O4 O 0.2821(9) 0.5019(3) 0.1834(2) 0.134(3) Uani 0.530(6) 1 d D U P A 1 O11 O 0.2573(12) 0.4067(3) 0.1832(3) 0.153(4) Uani 0.470(6) 1 d D U P A 2 O12 O 0.0215(8) 0.4330(5) 0.2465(3) 0.185(5) Uani 0.470(6) 1 d D U P A 2 O13 O 0.3173(7) 0.4899(3) 0.2602(3) 0.095(3) Uani 0.470(6) 1 d D U P A 2 O14 O 0.1075(8) 0.5196(2) 0.1786(2) 0.0650(18) Uani 0.470(6) 1 d D U P A 2 O41 O 0.2148(10) 0.8118(3) 0.4886(3) 0.070(2) Uiso 0.486(8) 1 d D U P B 1 C41 C 0.3911(16) 0.8349(7) 0.4562(6) 0.112(3) Uiso 0.486(8) 1 d D U P B 1 O42 O -0.047(2) 0.9383(10) 0.4543(8) 0.090(4) Uiso 0.207(8) 1 d D U P C 2 C42 C 0.152(3) 0.9369(16) 0.4909(13) 0.108(5) Uiso 0.207(8) 1 d D U P C 2 O43 O -0.0005(16) 0.9271(6) 0.5078(5) 0.082(3) Uiso 0.296(8) 1 d D U P D 4 C43 C -0.129(3) 0.8982(12) 0.4525(7) 0.100(4) Uiso 0.296(8) 1 d D U P D 4 O44 O -0.128(5) 0.9603(17) 0.5895(12) 0.089(5) Uiso 0.113(7) 1 d D U P E 5 C44 C -0.153(7) 0.951(2) 0.5201(13) 0.087(4) Uiso 0.113(7) 1 d D U P E 5 O51 O -0.325(2) 0.9429(6) 0.5622(5) 0.085(3) Uiso 0.326(10) 1 d D U P F 6 C51 C -0.340(3) 0.9897(10) 0.6194(6) 0.089(4) Uiso 0.326(10) 1 d D U P F 6 O52 O -0.648(4) 0.9855(17) 0.5554(14) 0.077(6) Uiso 0.095(6) 1 d D U P G 7 C52 C -0.451(7) 0.946(4) 0.565(3) 0.085(4) Uiso 0.095(6) 1 d D U P G 7 O53 O -0.248(2) 0.9582(8) 0.5520(8) 0.083(3) Uiso 0.239(9) 1 d D U P H 8 C53 C -0.423(3) 0.9106(11) 0.5285(11) 0.090(4) Uiso 0.239(9) 1 d D U P H 8 O55 O -0.397(4) 0.9611(15) 0.6171(11) 0.083(4) Uiso 0.149(9) 1 d D U P I 9 C55 C -0.504(5) 0.909(2) 0.5700(15) 0.086(5) Uiso 0.149(9) 1 d D U P I 9 O54 O -0.455(4) 0.9623(18) 0.5901(17) 0.088(4) Uiso 0.127(9) 1 d D U P J 10 C54 C -0.238(4) 0.962(2) 0.612(2) 0.085(4) Uiso 0.127(9) 1 d D U P J 10 O61 O 0.115(3) 0.8572(12) 0.4589(10) 0.104(3) Uiso 0.191(8) 1 d D U P K 11 C61 C 0.301(4) 0.8174(16) 0.4847(13) 0.085(4) Uiso 0.191(8) 1 d D U P K 11 O62 O 0.356(2) 0.8695(8) 0.5111(7) 0.106(4) Uiso 0.250(7) 1 d D U P L 12 C62 C 0.454(3) 0.9253(10) 0.4713(8) 0.087(5) Uiso 0.250(7) 1 d D U P L 12 O63 O 0.009(4) 0.8489(15) 0.4536(12) 0.093(4) Uiso 0.136(7) 1 d D U P M 13 C63 C 0.216(4) 0.853(2) 0.434(2) 0.103(4) Uiso 0.136(7) 1 d D U P M 13 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 0.03016(16) 0.04110(19) 0.01911(14) -0.00250(13) 0.00577(11) 0.00187(14) Cl5 0.0349(3) 0.0586(5) 0.0310(3) 0.0142(3) 0.0044(3) 0.0010(3) Cl15 0.0300(3) 0.0577(4) 0.0254(3) -0.0162(3) 0.0060(2) 0.0008(3) N1 0.0283(10) 0.0415(13) 0.0179(9) -0.0044(8) 0.0039(8) 0.0049(9) N2 0.0259(10) 0.0395(13) 0.0215(9) -0.0039(8) 0.0040(8) 0.0039(9) N3 0.0276(10) 0.0395(13) 0.0204(9) 0.0016(8) 0.0048(8) 0.0043(9) N4 0.0295(11) 0.0403(13) 0.0238(10) 0.0042(9) 0.0060(8) 0.0047(9) N11 0.0292(11) 0.0488(14) 0.0245(10) -0.0088(9) 0.0022(8) 0.0010(10) N12 0.090(2) 0.0580(18) 0.0239(11) -0.0053(11) 0.0018(12) 0.0335(16) N13 0.0340(12) 0.0574(16) 0.0245(10) -0.0160(10) 0.0019(9) 0.0050(11) N14 0.0337(12) 0.0577(16) 0.0307(12) -0.0212(11) 0.0056(9) 0.0020(11) C1 0.0292(13) 0.0433(16) 0.0263(12) 0.0035(11) 0.0047(10) 0.0057(11) C2 0.0261(12) 0.0496(16) 0.0198(11) 0.0061(10) 0.0045(9) 0.0049(11) C3 0.0376(14) 0.0514(18) 0.0210(12) 0.0018(11) 0.0039(10) 0.0047(12) C4 0.0425(16) 0.0448(17) 0.0320(14) 0.0053(12) 0.0010(12) 0.0052(13) C5 0.0245(12) 0.0521(18) 0.0268(12) 0.0106(11) 0.0037(10) 0.0043(11) C6 0.0333(13) 0.0583(19) 0.0205(11) 0.0013(11) 0.0079(10) 0.0075(13) C7 0.0356(14) 0.0468(17) 0.0292(13) 0.0019(11) 0.0058(11) 0.0054(12) C8 0.0300(12) 0.0442(17) 0.0205(11) -0.0003(10) 0.0045(9) 0.0081(11) C9 0.0313(12) 0.0387(15) 0.0220(11) -0.0006(10) 0.0052(9) 0.0030(11) C11 0.0264(13) 0.0597(19) 0.0317(14) -0.0190(13) 0.0005(11) 0.0012(12) C12 0.0216(12) 0.0593(19) 0.0310(13) -0.0200(12) 0.0042(10) -0.0027(12) C13 0.0379(15) 0.0559(19) 0.0284(13) -0.0150(12) 0.0122(11) -0.0138(13) C14 0.0377(14) 0.0493(17) 0.0321(13) -0.0158(12) 0.0099(11) -0.0121(13) C15 0.0226(12) 0.0559(19) 0.0265(12) -0.0172(12) 0.0036(10) -0.0028(11) C16 0.0338(14) 0.062(2) 0.0295(13) -0.0116(13) 0.0011(11) 0.0091(13) C17 0.0318(14) 0.063(2) 0.0297(13) -0.0153(13) -0.0010(11) 0.0086(13) C18 0.0284(13) 0.0495(17) 0.0257(12) -0.0130(11) 0.0075(10) -0.0060(12) C19 0.095(3) 0.066(2) 0.0238(14) -0.0072(14) 0.0004(16) 0.037(2) Cl1 0.0782(6) 0.0543(5) 0.0391(4) -0.0019(4) -0.0030(4) -0.0084(4) O1 0.071(3) 0.034(2) 0.079(3) -0.015(2) -0.011(3) -0.001(2) O2 0.078(4) 0.104(5) 0.143(6) -0.077(4) -0.035(4) 0.033(3) O3 0.062(3) 0.063(3) 0.048(3) -0.004(2) 0.002(2) 0.000(2) O4 0.178(7) 0.136(6) 0.097(5) 0.015(4) 0.055(5) -0.073(5) O11 0.219(9) 0.110(6) 0.118(6) -0.046(5) -0.040(6) 0.084(6) O12 0.128(7) 0.232(9) 0.195(8) 0.114(7) 0.024(6) -0.062(6) O13 0.072(4) 0.110(6) 0.098(5) -0.059(4) -0.029(4) 0.029(4) O14 0.075(4) 0.051(3) 0.070(4) 0.010(3) 0.011(3) -0.009(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N11 1.932(2) . ? Cu1 N1 1.941(2) 3_566 ? Cu1 N2 2.017(2) . ? Cl5 C5 1.739(3) . ? Cl15 C15 1.741(2) . ? N1 C8 1.320(3) . ? N1 N2 1.392(3) . ? N1 Cu1 1.941(2) 3_566 ? N2 C9 1.299(3) . ? N3 C8 1.352(3) . ? N3 C9 1.362(3) . ? N3 N4 1.399(3) . ? N4 C1 1.287(3) . ? N11 C18 1.311(3) . ? N11 N12 1.383(4) . ? N12 C19 1.307(4) . ? N13 C19 1.341(4) . ? N13 C18 1.359(4) . ? N13 N14 1.403(3) . ? N14 C11 1.270(4) . ? C1 C2 1.468(4) . ? C1 H1A 0.9300 . ? C2 C7 1.389(4) . ? C2 C3 1.397(4) . ? C3 C4 1.381(4) . ? C3 H3A 0.9300 . ? C4 C5 1.384(4) . ? C4 H4A 0.9300 . ? C5 C6 1.381(4) . ? C6 C7 1.390(4) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? C9 H9A 0.9300 . ? C11 C12 1.468(3) . ? C11 H11A 0.9300 . ? C12 C13 1.383(4) . ? C12 C17 1.391(4) . ? C13 C14 1.381(4) . ? C13 H13A 0.9300 . ? C14 C15 1.376(4) . ? C14 H14A 0.9300 . ? C15 C16 1.371(4) . ? C16 C17 1.397(4) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? Cl1 O4 1.348(3) . ? Cl1 O12 1.381(4) . ? Cl1 O11 1.395(4) . ? Cl1 O1 1.414(3) . ? Cl1 O13 1.421(3) . ? Cl1 O14 1.427(3) . ? Cl1 O2 1.435(3) . ? Cl1 O3 1.443(3) . ? O41 C41 1.536(9) . ? O42 C42 1.542(9) . ? O43 C43 1.540(9) . ? O44 C44 1.541(9) . ? O51 C51 1.538(9) . ? O52 C52 1.542(10) . ? O53 C53 1.543(9) . ? O55 C55 1.543(9) . ? O54 C54 1.541(9) . ? O61 C61 1.543(9) . ? O62 C62 1.544(9) . ? O63 C63 1.542(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cu1 N1 133.31(9) . 3_566 ? N11 Cu1 N2 111.74(9) . . ? N1 Cu1 N2 114.57(8) 3_566 . ? C8 N1 N2 107.4(2) . . ? C8 N1 Cu1 130.59(18) . 3_566 ? N2 N1 Cu1 121.86(15) . 3_566 ? C9 N2 N1 106.9(2) . . ? C9 N2 Cu1 129.92(18) . . ? N1 N2 Cu1 122.25(16) . . ? C8 N3 C9 105.9(2) . . ? C8 N3 N4 132.7(2) . . ? C9 N3 N4 121.4(2) . . ? C1 N4 N3 115.1(2) . . ? C18 N11 N12 108.2(2) . . ? C18 N11 Cu1 129.8(2) . . ? N12 N11 Cu1 121.95(16) . . ? C19 N12 N11 105.8(2) . . ? C19 N13 C18 105.5(2) . . ? C19 N13 N14 121.6(3) . . ? C18 N13 N14 133.0(2) . . ? C11 N14 N13 115.5(3) . . ? N4 C1 C2 119.9(3) . . ? N4 C1 H1A 120.1 . . ? C2 C1 H1A 120.1 . . ? C7 C2 C3 119.4(2) . . ? C7 C2 C1 118.2(3) . . ? C3 C2 C1 122.5(2) . . ? C4 C3 C2 120.8(3) . . ? C4 C3 H3A 119.6 . . ? C2 C3 H3A 119.6 . . ? C3 C4 C5 118.5(3) . . ? C3 C4 H4A 120.7 . . ? C5 C4 H4A 120.7 . . ? C6 C5 C4 122.2(3) . . ? C6 C5 Cl5 118.6(2) . . ? C4 C5 Cl5 119.2(2) . . ? C5 C6 C7 118.6(2) . . ? C5 C6 H6A 120.7 . . ? C7 C6 H6A 120.7 . . ? C2 C7 C6 120.5(3) . . ? C2 C7 H7A 119.7 . . ? C6 C7 H7A 119.7 . . ? N1 C8 N3 109.4(2) . . ? N1 C8 H8A 125.3 . . ? N3 C8 H8A 125.3 . . ? N2 C9 N3 110.4(2) . . ? N2 C9 H9A 124.8 . . ? N3 C9 H9A 124.8 . . ? N14 C11 C12 119.9(3) . . ? N14 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C13 C12 C17 119.7(2) . . ? C13 C12 C11 122.3(3) . . ? C17 C12 C11 118.0(3) . . ? C14 C13 C12 120.3(3) . . ? C14 C13 H13A 119.9 . . ? C12 C13 H13A 119.9 . . ? C15 C14 C13 119.3(3) . . ? C15 C14 H14A 120.3 . . ? C13 C14 H14A 120.3 . . ? C16 C15 C14 122.0(2) . . ? C16 C15 Cl15 118.5(2) . . ? C14 C15 Cl15 119.6(2) . . ? C15 C16 C17 118.6(3) . . ? C15 C16 H16A 120.7 . . ? C17 C16 H16A 120.7 . . ? C12 C17 C16 120.2(3) . . ? C12 C17 H17A 119.9 . . ? C16 C17 H17A 119.9 . . ? N11 C18 N13 109.1(3) . . ? N11 C18 H18A 125.5 . . ? N13 C18 H18A 125.5 . . ? N12 C19 N13 111.4(3) . . ? N12 C19 H19A 124.3 . . ? N13 C19 H19A 124.3 . . ? O12 Cl1 O11 112.3(3) . . ? O4 Cl1 O1 114.7(2) . . ? O12 Cl1 O13 110.2(3) . . ? O11 Cl1 O13 108.7(3) . . ? O12 Cl1 O14 109.8(3) . . ? O11 Cl1 O14 109.2(3) . . ? O13 Cl1 O14 106.5(2) . . ? O4 Cl1 O2 112.4(3) . . ? O1 Cl1 O2 106.3(2) . . ? O4 Cl1 O3 111.7(2) . . ? O1 Cl1 O3 106.5(2) . . ? O2 Cl1 O3 104.6(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 N2 C9 0.0(3) . . . . ? Cu1 N1 N2 C9 176.01(16) 3_566 . . . ? C8 N1 N2 Cu1 170.19(16) . . . . ? Cu1 N1 N2 Cu1 -13.8(2) 3_566 . . . ? C8 N3 N4 C1 6.8(4) . . . . ? C9 N3 N4 C1 -172.4(2) . . . . ? C18 N11 N12 C19 0.6(4) . . . . ? Cu1 N11 N12 C19 179.9(2) . . . . ? C19 N13 N14 C11 179.4(3) . . . . ? C18 N13 N14 C11 -1.2(4) . . . . ? N3 N4 C1 C2 179.7(2) . . . . ? N4 C1 C2 C7 179.2(2) . . . . ? N4 C1 C2 C3 -0.4(4) . . . . ? C7 C2 C3 C4 -0.2(4) . . . . ? C1 C2 C3 C4 179.3(2) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C3 C4 C5 Cl5 178.7(2) . . . . ? C4 C5 C6 C7 -0.3(4) . . . . ? Cl5 C5 C6 C7 -179.1(2) . . . . ? C3 C2 C7 C6 -0.2(4) . . . . ? C1 C2 C7 C6 -179.7(2) . . . . ? C5 C6 C7 C2 0.4(4) . . . . ? N2 N1 C8 N3 -0.3(3) . . . . ? Cu1 N1 C8 N3 -175.89(16) 3_566 . . . ? C9 N3 C8 N1 0.5(3) . . . . ? N4 N3 C8 N1 -178.8(2) . . . . ? N1 N2 C9 N3 0.4(3) . . . . ? Cu1 N2 C9 N3 -168.83(16) . . . . ? C8 N3 C9 N2 -0.6(3) . . . . ? N4 N3 C9 N2 178.82(19) . . . . ? N13 N14 C11 C12 179.4(2) . . . . ? N14 C11 C12 C13 0.6(4) . . . . ? N14 C11 C12 C17 -179.1(2) . . . . ? C17 C12 C13 C14 0.3(4) . . . . ? C11 C12 C13 C14 -179.4(2) . . . . ? C12 C13 C14 C15 0.0(4) . . . . ? C13 C14 C15 C16 0.1(4) . . . . ? C13 C14 C15 Cl15 179.9(2) . . . . ? C14 C15 C16 C17 -0.3(4) . . . . ? Cl15 C15 C16 C17 179.8(2) . . . . ? C13 C12 C17 C16 -0.6(4) . . . . ? C11 C12 C17 C16 179.1(2) . . . . ? C15 C16 C17 C12 0.6(4) . . . . ? N12 N11 C18 N13 -0.8(3) . . . . ? Cu1 N11 C18 N13 -179.98(17) . . . . ? C19 N13 C18 N11 0.6(3) . . . . ? N14 N13 C18 N11 -178.8(2) . . . . ? N11 N12 C19 N13 -0.2(4) . . . . ? C18 N13 C19 N12 -0.3(4) . . . . ? N14 N13 C19 N12 179.2(3) . . . . ? _refine_diff_density_max 0.803 _refine_diff_density_min -0.613 _refine_diff_density_rms 0.094 _database_code_depnum_ccdc_archive 'CCDC 949080' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1-CCl4 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; bis(\m~2~-4-(E)-(4-chlorobenzylidene)amino-4H-1,2,4-triazole)-bis((E)-4-(chlor obenzylidene)amino-4H-1,2,4-triazole)-di-copper(i) diperchlorate tetrachloromethane disolvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H28 Cl4 Cu2 N16, 2(Cl O4), 2(C Cl4)' _chemical_formula_sum 'C38 H28 Cl14 Cu2 N16 O8' _chemical_formula_weight 1460.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.971(2) _cell_length_b 17.912(3) _cell_length_c 22.289(3) _cell_angle_alpha 90 _cell_angle_beta 95.64(3) _cell_angle_gamma 90 _cell_volume 2769.6(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 838 _cell_measurement_theta_min 2.7494 _cell_measurement_theta_max 27.3419 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.751 _exptl_crystal_F_000 1456 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_absorpt_coefficient_mu 1.508 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11580 _diffrn_reflns_av_unetI/netI 0.3718 _diffrn_reflns_av_R_equivalents 0.1637 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.923 _diffrn_reflns_theta_max 27.403 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.862 _diffrn_measured_fraction_theta_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.862 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.862 _diffrn_reflns_point_group_measured_fraction_full 0.987 _reflns_number_total 5417 _reflns_number_gt 1847 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_structure_solution ; SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.) ; _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0213P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 5417 _refine_ls_number_parameters 352 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.2930 _refine_ls_R_factor_gt 0.1050 _refine_ls_wR_factor_ref 0.1983 _refine_ls_wR_factor_gt 0.1311 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.945 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.4490(2) 0.57501(9) 0.04781(6) 0.0226(4) Uani 1 1 d . . . . . Cl5 Cl 0.1278(5) 0.12139(19) 0.40603(12) 0.0339(9) Uani 1 1 d . U . . . Cl15 Cl 0.0636(4) 0.93303(18) 0.45957(11) 0.0255(8) Uani 1 1 d . U . . . N1 N 0.4313(13) 0.4715(5) 0.0733(3) 0.017(2) Uani 1 1 d . . . . . N2 N 0.4463(12) 0.4133(5) 0.0337(3) 0.017(2) Uani 1 1 d . U . . . N3 N 0.3691(13) 0.3675(6) 0.1184(4) 0.023(2) Uani 1 1 d . U . . . N4 N 0.3287(13) 0.3111(5) 0.1595(3) 0.018(3) Uani 1 1 d . . . . . N11 N 0.3715(13) 0.6693(5) 0.0805(4) 0.020(3) Uani 1 1 d . . . . . N12 N 0.3566(14) 0.7351(6) 0.0464(4) 0.028(3) Uani 1 1 d . U . . . N13 N 0.2891(14) 0.7590(6) 0.1396(4) 0.026(3) Uani 1 1 d . U . . . N14 N 0.2398(14) 0.8044(5) 0.1861(4) 0.023(3) Uani 1 1 d . . . . . C1 C 0.3189(16) 0.3337(7) 0.2140(5) 0.021(3) Uani 1 1 d . U . . . H1A H 0.3397 0.3847 0.2244 0.025 Uiso 1 1 calc R U . . . C2 C 0.2746(16) 0.2787(7) 0.2600(5) 0.017(3) Uani 1 1 d . U . . . C3 C 0.2425(16) 0.2040(7) 0.2470(5) 0.024(3) Uani 1 1 d . . . . . H3A H 0.2505 0.1858 0.2072 0.029 Uiso 1 1 calc R U . . . C4 C 0.1988(15) 0.1561(7) 0.2920(5) 0.020(3) Uani 1 1 d . . . . . H4A H 0.1790 0.1046 0.2836 0.024 Uiso 1 1 calc R U . . . C5 C 0.1837(18) 0.1831(8) 0.3495(5) 0.031(3) Uani 1 1 d . U . . . C6 C 0.2117(17) 0.2572(7) 0.3635(5) 0.024(3) Uani 1 1 d . . . . . H6A H 0.2020 0.2749 0.4033 0.029 Uiso 1 1 calc R U . . . C7 C 0.2546(16) 0.3057(7) 0.3178(4) 0.021(3) Uani 1 1 d . . . . . H7A H 0.2704 0.3575 0.3260 0.025 Uiso 1 1 calc R U . . . C8 C 0.3868(16) 0.4421(7) 0.1240(4) 0.020(3) Uani 1 1 d . U . . . H8A H 0.3696 0.4695 0.1595 0.024 Uiso 1 1 calc R U . . . C9 C 0.4092(16) 0.3527(7) 0.0622(4) 0.022(3) Uani 1 1 d . U . . . H9A H 0.4104 0.3040 0.0453 0.026 Uiso 1 1 calc R U . . . C11 C 0.2327(15) 0.7709(7) 0.2377(4) 0.019(3) Uani 1 1 d . . . . . H11A H 0.2582 0.7188 0.2409 0.022 Uiso 1 1 calc R U . . . C12 C 0.1863(16) 0.8123(8) 0.2899(4) 0.025(4) Uani 1 1 d . . . . . C13 C 0.1452(17) 0.8884(7) 0.2875(5) 0.024(3) Uani 1 1 d . . . . . H13A H 0.1441 0.9150 0.2506 0.029 Uiso 1 1 calc R U . . . C14 C 0.1061(15) 0.9247(7) 0.3399(4) 0.021(3) Uani 1 1 d . U . . . H14A H 0.0754 0.9764 0.3387 0.025 Uiso 1 1 calc R U . . . C15 C 0.1114(16) 0.8859(7) 0.3945(4) 0.021(2) Uani 1 1 d . U . . . C16 C 0.1526(16) 0.8112(7) 0.3974(5) 0.019(3) Uani 1 1 d . U . . . H16A H 0.1548 0.7852 0.4347 0.023 Uiso 1 1 calc R U . . . C17 C 0.1914(15) 0.7736(8) 0.3451(5) 0.031(4) Uani 1 1 d . . . . . H17A H 0.2213 0.7219 0.3467 0.037 Uiso 1 1 calc R U . . . C18 C 0.3280(18) 0.6850(8) 0.1350(5) 0.027(3) Uani 1 1 d . . . . . H18A H 0.3243 0.6497 0.1667 0.032 Uiso 1 1 calc R U . . . C19 C 0.3077(17) 0.7874(7) 0.0840(4) 0.027(3) Uani 1 1 d . U . . . H19A H 0.2881 0.8384 0.0734 0.033 Uiso 1 1 calc R U . . . Cl1 Cl 0.3238(5) 0.5409(2) 0.28057(13) 0.0332(9) Uani 1 1 d . . . . . O1 O 0.2115(11) 0.5513(5) 0.2225(3) 0.035(2) Uani 1 1 d . . . . . O2 O 0.4902(14) 0.4960(6) 0.2711(4) 0.061(3) Uani 1 1 d . . . . . O3 O 0.3855(13) 0.6114(5) 0.3043(3) 0.046(3) Uani 1 1 d . . . . . O4 O 0.2096(15) 0.5036(6) 0.3201(4) 0.066(3) Uani 1 1 d . . . . . C21 C 0.261(2) 0.4108(10) 0.5333(6) 0.064(5) Uani 1 1 d . . . . . Cl21 Cl 0.0764(8) 0.3470(4) 0.5373(2) 0.123(2) Uani 1 1 d . . . . . Cl22 Cl 0.2570(7) 0.4780(3) 0.59076(17) 0.0858(17) Uani 1 1 d . . . . . Cl23 Cl 0.2423(7) 0.4543(3) 0.46320(17) 0.0837(16) Uani 1 1 d . . . . . Cl24 Cl 0.4808(7) 0.3636(3) 0.54434(19) 0.0855(16) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0318(11) 0.0222(10) 0.0148(7) -0.0010(7) 0.0078(6) -0.0023(9) Cl5 0.036(2) 0.037(2) 0.0292(17) 0.0162(16) 0.0078(14) -0.0008(19) Cl15 0.028(2) 0.032(2) 0.0175(15) -0.0055(14) 0.0071(12) 0.0043(18) N1 0.036(7) 0.007(6) 0.009(5) 0.001(4) 0.004(4) -0.002(5) N2 0.016(5) 0.027(6) 0.008(5) 0.001(4) 0.003(4) 0.015(5) N3 0.024(5) 0.030(6) 0.014(4) 0.001(4) 0.005(4) -0.004(5) N4 0.025(7) 0.025(7) 0.004(5) 0.007(4) 0.000(4) 0.007(5) N11 0.030(7) 0.022(7) 0.008(5) -0.002(4) 0.004(4) -0.012(6) N12 0.038(7) 0.024(7) 0.021(5) -0.001(5) 0.003(4) -0.006(5) N13 0.031(7) 0.033(7) 0.014(5) 0.000(5) 0.006(4) -0.005(6) N14 0.036(8) 0.025(7) 0.009(5) -0.011(5) 0.007(4) -0.006(6) C1 0.025(7) 0.012(7) 0.027(6) 0.006(5) 0.004(5) 0.006(6) C2 0.016(7) 0.009(7) 0.026(6) 0.011(5) 0.008(5) 0.007(6) C3 0.017(9) 0.041(10) 0.014(6) 0.005(6) 0.002(5) 0.012(7) C4 0.020(8) 0.011(8) 0.028(7) -0.001(6) 0.003(6) 0.000(7) C5 0.027(7) 0.036(7) 0.029(6) 0.012(6) 0.007(5) -0.006(6) C6 0.027(9) 0.026(9) 0.021(7) 0.010(6) 0.010(6) 0.010(7) C7 0.026(9) 0.012(8) 0.025(7) 0.003(6) 0.003(6) 0.016(7) C8 0.028(7) 0.022(7) 0.011(5) -0.001(5) 0.002(4) 0.002(6) C9 0.024(6) 0.027(6) 0.013(5) 0.003(5) 0.000(4) 0.000(5) C11 0.013(8) 0.022(9) 0.021(7) -0.002(6) 0.006(5) 0.006(7) C12 0.010(8) 0.056(11) 0.008(6) -0.003(6) -0.001(5) -0.008(7) C13 0.035(9) 0.015(9) 0.023(7) 0.005(6) 0.008(6) 0.010(7) C14 0.026(7) 0.025(7) 0.011(5) 0.003(5) -0.004(4) -0.003(6) C15 0.023(5) 0.027(5) 0.013(4) -0.006(4) 0.005(4) 0.007(5) C16 0.018(7) 0.022(7) 0.016(5) 0.008(5) -0.002(5) 0.007(6) C17 0.010(8) 0.056(11) 0.026(7) -0.004(7) -0.001(5) 0.009(8) C18 0.037(10) 0.033(10) 0.010(6) 0.005(6) -0.002(5) -0.008(8) C19 0.041(7) 0.030(7) 0.011(5) 0.004(5) 0.001(5) -0.005(6) Cl1 0.050(3) 0.027(2) 0.0221(18) -0.0027(16) 0.0058(16) 0.000(2) O1 0.027(6) 0.048(7) 0.028(5) 0.000(4) 0.000(4) -0.004(5) O2 0.057(8) 0.057(8) 0.064(6) -0.020(6) -0.026(5) 0.019(7) O3 0.055(7) 0.035(7) 0.044(5) -0.011(5) -0.012(5) -0.004(6) O4 0.113(10) 0.056(8) 0.034(5) 0.009(5) 0.026(6) -0.022(7) C21 0.047(12) 0.091(16) 0.053(9) 0.009(10) 0.005(8) 0.033(11) Cl21 0.124(6) 0.131(6) 0.113(4) 0.025(4) 0.004(4) -0.067(4) Cl22 0.113(4) 0.075(4) 0.070(3) -0.024(3) 0.015(3) 0.014(3) Cl23 0.112(4) 0.083(4) 0.053(2) 0.019(3) -0.004(2) -0.016(3) Cl24 0.116(5) 0.065(4) 0.078(3) 0.006(3) 0.024(3) 0.026(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N11 1.936(9) . ? Cu1 N1 1.947(9) . ? Cu1 N2 2.033(7) 3_665 ? Cl5 C5 1.748(12) . ? Cl15 C15 1.739(10) . ? N1 C8 1.310(11) . ? N1 N2 1.377(11) . ? N2 C9 1.297(13) . ? N2 Cu1 2.033(7) 3_665 ? N3 C9 1.337(11) . ? N3 C8 1.346(14) . ? N3 N4 1.410(11) . ? N4 C1 1.288(11) . ? N11 C18 1.312(12) . ? N11 N12 1.400(12) . ? N12 C19 1.324(13) . ? N13 C19 1.357(12) . ? N13 C18 1.359(15) . ? N13 N14 1.388(11) . ? N14 C11 1.301(12) . ? C1 C2 1.476(13) . ? C1 H1A 0.9500 . ? C2 C3 1.383(15) . ? C2 C7 1.396(13) . ? C3 C4 1.377(14) . ? C3 H3A 0.9500 . ? C4 C5 1.383(14) . ? C4 H4A 0.9500 . ? C5 C6 1.373(17) . ? C6 C7 1.394(14) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C11 C12 1.445(14) . ? C11 H11A 0.9500 . ? C12 C13 1.393(16) . ? C12 C17 1.408(15) . ? C13 C14 1.386(13) . ? C13 H13A 0.9500 . ? C14 C15 1.399(13) . ? C14 H14A 0.9500 . ? C15 C16 1.369(15) . ? C16 C17 1.396(14) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? Cl1 O4 1.411(8) . ? Cl1 O3 1.419(9) . ? Cl1 O2 1.444(9) . ? Cl1 O1 1.457(8) . ? C21 Cl21 1.729(17) . ? C21 Cl23 1.741(14) . ? C21 Cl24 1.747(15) . ? C21 Cl22 1.759(16) . ? 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 N11 Cu1 N1 133.9(3) . . ? N11 Cu1 N2 112.6(4) . 3_665 ? N1 Cu1 N2 113.4(3) . 3_665 ? C8 N1 N2 106.8(9) . . ? C8 N1 Cu1 131.4(8) . . ? N2 N1 Cu1 121.5(6) . . ? C9 N2 N1 106.7(8) . . ? C9 N2 Cu1 129.1(8) . 3_665 ? N1 N2 Cu1 123.5(7) . 3_665 ? C9 N3 C8 104.9(9) . . ? C9 N3 N4 122.7(10) . . ? C8 N3 N4 132.4(9) . . ? C1 N4 N3 114.8(9) . . ? C18 N11 N12 108.1(10) . . ? C18 N11 Cu1 129.3(9) . . ? N12 N11 Cu1 122.6(6) . . ? C19 N12 N11 105.3(8) . . ? C19 N13 C18 105.0(9) . . ? C19 N13 N14 121.0(10) . . ? C18 N13 N14 133.9(9) . . ? C11 N14 N13 115.0(10) . . ? N4 C1 C2 118.6(11) . . ? N4 C1 H1A 120.7 . . ? C2 C1 H1A 120.7 . . ? C3 C2 C7 120.0(10) . . ? C3 C2 C1 122.8(10) . . ? C7 C2 C1 117.1(11) . . ? C4 C3 C2 119.5(10) . . ? C4 C3 H3A 120.3 . . ? C2 C3 H3A 120.3 . . ? C3 C4 C5 120.1(11) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C6 C5 C4 121.7(11) . . ? C6 C5 Cl5 119.0(9) . . ? C4 C5 Cl5 119.3(10) . . ? C5 C6 C7 118.2(10) . . ? C5 C6 H6A 120.9 . . ? C7 C6 H6A 120.9 . . ? C6 C7 C2 120.5(11) . . ? C6 C7 H7A 119.8 . . ? C2 C7 H7A 119.8 . . ? N1 C8 N3 110.3(9) . . ? N1 C8 H8A 124.8 . . ? N3 C8 H8A 124.8 . . ? N2 C9 N3 111.3(11) . . ? N2 C9 H9A 124.3 . . ? N3 C9 H9A 124.3 . . ? N14 C11 C12 120.4(11) . . ? N14 C11 H11A 119.8 . . ? C12 C11 H11A 119.8 . . ? C13 C12 C17 120.1(11) . . ? C13 C12 C11 122.2(10) . . ? C17 C12 C11 117.6(12) . . ? C14 C13 C12 118.9(10) . . ? C14 C13 H13A 120.6 . . ? C12 C13 H13A 120.6 . . ? C13 C14 C15 120.6(11) . . ? C13 C14 H14A 119.7 . . ? C15 C14 H14A 119.7 . . ? C16 C15 C14 121.0(10) . . ? C16 C15 Cl15 119.4(8) . . ? C14 C15 Cl15 119.6(9) . . ? C15 C16 C17 119.2(10) . . ? C15 C16 H16A 120.4 . . ? C17 C16 H16A 120.4 . . ? C16 C17 C12 120.2(12) . . ? C16 C17 H17A 119.9 . . ? C12 C17 H17A 119.9 . . ? N11 C18 N13 110.2(10) . . ? N11 C18 H18A 124.9 . . ? N13 C18 H18A 124.9 . . ? N12 C19 N13 111.4(11) . . ? N12 C19 H19A 124.3 . . ? N13 C19 H19A 124.3 . . ? O4 Cl1 O3 111.0(5) . . ? O4 Cl1 O2 109.8(6) . . ? O3 Cl1 O2 109.3(6) . . ? O4 Cl1 O1 109.1(6) . . ? O3 Cl1 O1 109.5(5) . . ? O2 Cl1 O1 108.1(5) . . ? Cl21 C21 Cl23 110.6(9) . . ? Cl21 C21 Cl24 108.7(10) . . ? Cl23 C21 Cl24 109.2(7) . . ? Cl21 C21 Cl22 110.5(7) . . ? Cl23 C21 Cl22 110.0(10) . . ? Cl24 C21 Cl22 107.8(8) . . ? 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 C8 N1 N2 C9 0.4(12) . . . . ? Cu1 N1 N2 C9 -173.6(8) . . . . ? C8 N1 N2 Cu1 -170.6(7) . . . 3_665 ? Cu1 N1 N2 Cu1 15.4(11) . . . 3_665 ? C9 N3 N4 C1 171.0(10) . . . . ? C8 N3 N4 C1 -5.3(17) . . . . ? C18 N11 N12 C19 1.2(12) . . . . ? Cu1 N11 N12 C19 -177.8(8) . . . . ? C19 N13 N14 C11 -177.9(10) . . . . ? C18 N13 N14 C11 2.0(18) . . . . ? N3 N4 C1 C2 179.2(9) . . . . ? N4 C1 C2 C3 -0.2(17) . . . . ? N4 C1 C2 C7 -176.6(11) . . . . ? C7 C2 C3 C4 -2.7(17) . . . . ? C1 C2 C3 C4 -178.9(10) . . . . ? C2 C3 C4 C5 1.2(17) . . . . ? C3 C4 C5 C6 -0.1(19) . . . . ? C3 C4 C5 Cl5 179.9(9) . . . . ? C4 C5 C6 C7 0.5(19) . . . . ? Cl5 C5 C6 C7 -179.5(9) . . . . ? C5 C6 C7 C2 -2.1(18) . . . . ? C3 C2 C7 C6 3.2(18) . . . . ? C1 C2 C7 C6 179.6(10) . . . . ? N2 N1 C8 N3 -1.1(12) . . . . ? Cu1 N1 C8 N3 172.1(8) . . . . ? C9 N3 C8 N1 1.4(13) . . . . ? N4 N3 C8 N1 178.1(10) . . . . ? N1 N2 C9 N3 0.5(12) . . . . ? Cu1 N2 C9 N3 170.8(7) 3_665 . . . ? C8 N3 C9 N2 -1.1(13) . . . . ? N4 N3 C9 N2 -178.3(9) . . . . ? N13 N14 C11 C12 178.9(9) . . . . ? N14 C11 C12 C13 0.9(17) . . . . ? N14 C11 C12 C17 -176.5(11) . . . . ? C17 C12 C13 C14 -1.3(18) . . . . ? C11 C12 C13 C14 -178.6(10) . . . . ? C12 C13 C14 C15 1.2(17) . . . . ? C13 C14 C15 C16 -0.9(18) . . . . ? C13 C14 C15 Cl15 179.5(9) . . . . ? C14 C15 C16 C17 0.5(18) . . . . ? Cl15 C15 C16 C17 -179.8(8) . . . . ? C15 C16 C17 C12 -0.6(17) . . . . ? C13 C12 C17 C16 0.9(18) . . . . ? C11 C12 C17 C16 178.4(10) . . . . ? N12 N11 C18 N13 -1.5(13) . . . . ? Cu1 N11 C18 N13 177.4(8) . . . . ? C19 N13 C18 N11 1.2(14) . . . . ? N14 N13 C18 N11 -178.8(11) . . . . ? N11 N12 C19 N13 -0.5(13) . . . . ? C18 N13 C19 N12 -0.4(13) . . . . ? N14 N13 C19 N12 179.5(10) . . . . ? _refine_diff_density_max 0.614 _refine_diff_density_min -0.637 _refine_diff_density_rms 0.138 _database_code_depnum_ccdc_archive 'CCDC 949081' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1-C7H8 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; bis(\m~2~-4-(E)-(4-chlorobenzylidene)amino-4H-1,2,4-triazole)-bis((E)-4-(chlor obenzylidene)amino-4H-1,2,4-triazole)-di-copper(i) diperchlorate toluene disolvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H28 Cl4 Cu2 N16, 2(Cl O4), 2(C7 H8)' _chemical_formula_sum 'C50 H44 Cl6 Cu2 N16 O8' _chemical_formula_weight 1336.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.999(2) _cell_length_b 17.994(3) _cell_length_c 22.019(3) _cell_angle_alpha 90 _cell_angle_beta 95.67(3) _cell_angle_gamma 90 _cell_volume 2759.5(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2153 _cell_measurement_theta_min 2.9167 _cell_measurement_theta_max 28.8335 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.609 _exptl_crystal_F_000 1360 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_absorpt_coefficient_mu 1.131 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18490 _diffrn_reflns_av_unetI/netI 0.3463 _diffrn_reflns_av_R_equivalents 0.2296 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.925 _diffrn_reflns_theta_max 26.999 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.985 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.985 _diffrn_reflns_point_group_measured_fraction_full 0.992 _reflns_number_total 5926 _reflns_number_gt 1938 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_structure_solution ; SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.) ; _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0174P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 5926 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2272 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1046 _refine_ls_wR_factor_gt 0.0753 _refine_ls_goodness_of_fit_ref 0.777 _refine_ls_restrained_S_all 0.777 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.02856(10) 0.42812(5) 0.44996(3) 0.0238(2) Uani 1 1 d . . . . . Cl1 Cl 0.1506(3) 0.46206(12) 0.21301(8) 0.0392(5) Uani 1 1 d . . . . . O1 O 0.2981(7) 0.4812(3) 0.2594(2) 0.090(2) Uani 1 1 d . . . . . O2 O 0.0723(7) 0.5261(3) 0.1828(2) 0.0569(15) Uani 1 1 d . . . . . O3 O 0.2293(9) 0.4149(3) 0.1713(2) 0.097(2) Uani 1 1 d . . . . . O4 O 0.0089(7) 0.4256(5) 0.2412(3) 0.145(3) Uani 1 1 d . . . . . N1 N 0.0932(6) 0.5286(3) 0.4289(2) 0.0166(13) Uani 1 1 d . . . . . N2 N 0.0846(6) 0.5859(3) 0.4708(2) 0.0169(13) Uani 1 1 d . . . . . N3 N 0.1753(7) 0.6310(3) 0.3857(2) 0.0210(14) Uani 1 1 d . . . . . N4 N 0.2251(7) 0.6877(3) 0.3459(2) 0.0219(13) Uani 1 1 d . . . . . C1 C 0.2453(8) 0.6659(4) 0.2917(3) 0.0204(17) Uani 1 1 d . . . . . H1A H 0.2277 0.6150 0.2808 0.024 Uiso 1 1 calc R U . . . C2 C 0.2960(8) 0.7203(4) 0.2465(3) 0.0203(16) Uani 1 1 d . . . . . C3 C 0.3250(8) 0.7947(4) 0.2596(3) 0.0226(17) Uani 1 1 d . . . . . H3A H 0.3115 0.8126 0.2995 0.027 Uiso 1 1 calc R U . . . C4 C 0.3732(8) 0.8431(4) 0.2154(3) 0.0280(18) Uani 1 1 d . . . . . H4A H 0.3968 0.8939 0.2250 0.034 Uiso 1 1 calc R U . . . C5 C 0.3872(8) 0.8174(4) 0.1569(3) 0.0278(18) Uani 1 1 d . . . . . Cl5 Cl 0.4373(2) 0.87803(10) 0.09946(8) 0.0332(5) Uani 1 1 d . . . . . C6 C 0.3595(8) 0.7434(4) 0.1429(3) 0.0215(17) Uani 1 1 d . . . . . H6A H 0.3725 0.7262 0.1027 0.026 Uiso 1 1 calc R U . . . C7 C 0.3124(8) 0.6938(4) 0.1874(3) 0.0209(17) Uani 1 1 d . . . . . H7A H 0.2917 0.6427 0.1779 0.025 Uiso 1 1 calc R U . . . C8 C 0.1487(7) 0.5572(4) 0.3792(3) 0.0184(16) Uani 1 1 d . . . . . H8A H 0.1676 0.5298 0.3434 0.022 Uiso 1 1 calc R U . . . C9 C 0.1337(8) 0.6462(4) 0.4436(3) 0.0234(17) Uani 1 1 d . . . . . H9A H 0.1397 0.6942 0.4616 0.028 Uiso 1 1 calc R U . . . N11 N 0.0657(7) 0.3331(3) 0.4123(2) 0.0209(14) Uani 1 1 d . . . . . N12 N 0.0628(8) 0.2671(3) 0.4449(2) 0.0302(15) Uani 1 1 d . . . . . N13 N 0.1340(7) 0.2449(3) 0.3514(2) 0.0224(14) Uani 1 1 d . . . . . N14 N 0.1824(7) 0.2010(3) 0.3031(2) 0.0235(14) Uani 1 1 d . . . . . C11 C 0.1962(8) 0.2326(4) 0.2516(3) 0.0219(17) Uani 1 1 d . . . . . H11A H 0.1700 0.2842 0.2473 0.026 Uiso 1 1 calc R U . . . C12 C 0.2502(8) 0.1915(4) 0.2007(3) 0.0202(16) Uani 1 1 d . . . . . C13 C 0.2860(8) 0.1153(4) 0.2049(3) 0.0294(19) Uani 1 1 d . . . . . H13A H 0.2777 0.0900 0.2425 0.035 Uiso 1 1 calc R U . . . C14 C 0.3342(7) 0.0762(4) 0.1538(3) 0.0258(16) Uani 1 1 d . . . . . H14A H 0.3590 0.0243 0.1557 0.031 Uiso 1 1 calc R U . . . C15 C 0.3448(8) 0.1152(4) 0.1002(3) 0.0219(17) Uani 1 1 d . . . . . Cl15 Cl 0.40362(19) 0.06501(10) 0.03634(6) 0.0262(4) Uani 1 1 d . . . . . C16 C 0.3103(8) 0.1889(4) 0.0944(3) 0.0220(17) Uani 1 1 d . . . . . H16A H 0.3191 0.2137 0.0566 0.026 Uiso 1 1 calc R U . . . C17 C 0.2614(8) 0.2271(4) 0.1455(3) 0.0271(18) Uani 1 1 d . . . . . H17A H 0.2351 0.2789 0.1424 0.033 Uiso 1 1 calc R U . . . C18 C 0.1064(8) 0.3179(4) 0.3570(3) 0.0220(17) Uani 1 1 d . . . . . H18A H 0.1150 0.3534 0.3254 0.026 Uiso 1 1 calc R U . . . C19 C 0.1030(8) 0.2148(4) 0.4067(3) 0.0269(18) Uani 1 1 d . . . . . H19A H 0.1097 0.1633 0.4161 0.032 Uiso 1 1 calc R U . . . C21 C 0.4270(9) 0.5816(4) 0.0408(3) 0.0331(19) Uani 1 1 d . . . . . C22 C 0.2310(10) 0.5667(5) 0.0373(3) 0.045(2) Uani 1 1 d . . . . . H22A H 0.1806 0.5381 0.0683 0.054 Uiso 1 1 calc R U . . . C23 C 0.1084(10) 0.5936(4) -0.0114(4) 0.050(2) Uani 1 1 d . . . . . H23A H -0.0248 0.5823 -0.0142 0.060 Uiso 1 1 calc R U . . . C24 C 0.1808(11) 0.6369(4) -0.0559(4) 0.047(2) Uani 1 1 d . . . . . H24A H 0.0968 0.6566 -0.0885 0.057 Uiso 1 1 calc R U . . . C25 C 0.3710(11) 0.6511(4) -0.0527(3) 0.046(2) Uani 1 1 d . . . . . H25A H 0.4206 0.6800 -0.0837 0.055 Uiso 1 1 calc R U . . . C26 C 0.4949(10) 0.6239(4) -0.0049(3) 0.041(2) Uani 1 1 d . . . . . H26A H 0.6282 0.6346 -0.0034 0.050 Uiso 1 1 calc R U . . . C27 C 0.5627(9) 0.5507(4) 0.0923(3) 0.042(2) Uani 1 1 d . . . . . H27A H 0.6941 0.5666 0.0871 0.063 Uiso 1 1 calc R U . . . H27B H 0.5561 0.4963 0.0918 0.063 Uiso 1 1 calc R U . . . H27C H 0.5260 0.5693 0.1313 0.063 Uiso 1 1 calc R U . . . 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 0.0254(4) 0.0257(5) 0.0212(5) -0.0003(5) 0.0066(4) -0.0005(5) Cl1 0.0473(13) 0.0373(13) 0.0323(12) 0.0032(10) 0.0007(10) -0.0045(11) O1 0.062(4) 0.111(6) 0.086(4) -0.066(4) -0.046(4) 0.047(4) O2 0.061(4) 0.029(3) 0.079(4) 0.018(3) 0.000(3) 0.010(3) O3 0.143(5) 0.080(5) 0.063(4) -0.038(4) -0.017(4) 0.054(5) O4 0.065(4) 0.185(8) 0.187(7) 0.136(7) 0.024(4) -0.024(5) N1 0.013(3) 0.020(3) 0.017(3) -0.001(3) 0.004(2) -0.001(3) N2 0.019(3) 0.019(4) 0.014(3) -0.009(3) 0.003(2) 0.000(3) N3 0.021(3) 0.026(4) 0.017(3) 0.000(3) 0.005(3) 0.000(3) N4 0.018(3) 0.022(4) 0.026(3) 0.006(3) 0.005(3) 0.000(3) C1 0.018(4) 0.025(5) 0.018(4) 0.004(3) 0.004(3) 0.002(3) C2 0.010(4) 0.023(5) 0.028(4) -0.004(4) -0.001(3) 0.005(3) C3 0.029(4) 0.021(5) 0.017(4) -0.005(3) 0.001(3) 0.003(4) C4 0.026(4) 0.029(5) 0.029(4) 0.000(4) 0.006(4) -0.001(4) C5 0.019(4) 0.031(5) 0.035(5) 0.014(4) 0.006(3) -0.001(4) Cl5 0.0314(10) 0.0373(13) 0.0315(10) 0.0153(9) 0.0065(8) -0.0019(9) C6 0.015(4) 0.037(5) 0.014(4) 0.006(4) 0.003(3) 0.001(4) C7 0.018(4) 0.025(4) 0.021(4) -0.003(3) 0.009(3) -0.005(3) C8 0.011(3) 0.023(5) 0.023(4) -0.003(3) 0.008(3) 0.003(3) C9 0.018(4) 0.030(5) 0.021(4) 0.003(4) 0.000(3) 0.001(4) N11 0.020(3) 0.016(4) 0.028(4) -0.006(3) 0.004(3) -0.006(3) N12 0.045(4) 0.024(4) 0.023(3) -0.003(3) 0.008(3) 0.008(3) N13 0.021(3) 0.025(4) 0.023(4) -0.004(3) 0.007(3) 0.001(3) N14 0.025(3) 0.026(4) 0.021(3) -0.008(3) 0.006(3) -0.001(3) C11 0.011(4) 0.025(5) 0.030(4) -0.003(4) 0.004(3) -0.001(3) C12 0.012(4) 0.020(5) 0.028(4) -0.004(4) 0.002(3) 0.000(3) C13 0.032(4) 0.047(6) 0.009(4) -0.003(4) 0.000(3) -0.008(4) C14 0.025(4) 0.031(5) 0.020(4) 0.003(4) 0.000(3) -0.004(4) C15 0.015(4) 0.037(5) 0.014(4) -0.009(4) 0.005(3) -0.001(4) Cl15 0.0222(9) 0.0339(11) 0.0236(9) -0.0068(9) 0.0070(7) 0.0014(9) C16 0.016(4) 0.025(5) 0.027(4) -0.001(4) 0.006(3) -0.003(3) C17 0.023(4) 0.028(5) 0.031(5) 0.004(4) 0.005(3) -0.005(4) C18 0.021(4) 0.027(5) 0.019(4) -0.003(4) 0.005(3) 0.004(4) C19 0.022(4) 0.027(5) 0.032(5) 0.007(4) 0.001(4) 0.000(4) C21 0.035(4) 0.031(5) 0.034(5) -0.001(4) 0.010(4) 0.006(4) C22 0.045(5) 0.054(6) 0.039(5) -0.003(5) 0.017(4) -0.012(5) C23 0.038(5) 0.058(7) 0.055(6) -0.015(5) 0.010(5) -0.006(5) C24 0.048(6) 0.040(6) 0.053(6) 0.002(5) 0.003(5) 0.007(5) C25 0.048(6) 0.043(6) 0.047(5) 0.004(4) 0.008(5) -0.009(5) C26 0.036(5) 0.046(6) 0.041(5) -0.007(4) -0.002(4) -0.005(4) C27 0.059(5) 0.027(5) 0.041(5) 0.005(4) 0.006(4) 0.002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N11 1.929(5) . ? Cu N1 1.931(5) . ? Cu N2 2.002(5) 3_566 ? Cl1 O4 1.386(5) . ? Cl1 O3 1.403(5) . ? Cl1 O2 1.413(5) . ? Cl1 O1 1.420(5) . ? N1 C8 1.304(6) . ? N1 N2 1.389(6) . ? N2 C9 1.301(7) . ? N2 Cu 2.002(5) 3_566 ? N3 C8 1.347(8) . ? N3 C9 1.363(7) . ? N3 N4 1.411(6) . ? N4 C1 1.278(7) . ? C1 C2 1.465(8) . ? C1 H1A 0.9500 . ? C2 C3 1.379(8) . ? C2 C7 1.403(8) . ? C3 C4 1.372(8) . ? C3 H3A 0.9500 . ? C4 C5 1.381(8) . ? C4 H4A 0.9500 . ? C5 C6 1.376(8) . ? C5 Cl5 1.732(6) . ? C6 C7 1.388(8) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? N11 C18 1.307(7) . ? N11 N12 1.389(6) . ? N12 C19 1.311(7) . ? N13 C18 1.336(7) . ? N13 C19 1.369(7) . ? N13 N14 1.393(6) . ? N14 C11 1.280(7) . ? C11 C12 1.425(8) . ? C11 H11A 0.9500 . ? C12 C17 1.385(8) . ? C12 C13 1.395(8) . ? C13 C14 1.398(8) . ? C13 H13A 0.9500 . ? C14 C15 1.380(8) . ? C14 H14A 0.9500 . ? C15 C16 1.351(8) . ? C15 Cl15 1.755(6) . ? C16 C17 1.390(8) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C21 C26 1.383(9) . ? C21 C22 1.392(8) . ? C21 C27 1.511(8) . ? C22 C23 1.393(9) . ? C22 H22A 0.9500 . ? C23 C24 1.386(9) . ? C23 H23A 0.9500 . ? C24 C25 1.351(9) . ? C24 H24A 0.9500 . ? C25 C26 1.386(8) . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 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 N11 Cu N1 133.0(2) . . ? N11 Cu N2 110.2(2) . 3_566 ? N1 Cu N2 116.71(18) . 3_566 ? O4 Cl1 O3 110.6(5) . . ? O4 Cl1 O2 109.6(4) . . ? O3 Cl1 O2 110.1(3) . . ? O4 Cl1 O1 107.1(4) . . ? O3 Cl1 O1 108.2(3) . . ? O2 Cl1 O1 111.1(4) . . ? C8 N1 N2 107.5(5) . . ? C8 N1 Cu 131.9(5) . . ? N2 N1 Cu 120.7(4) . . ? C9 N2 N1 106.5(5) . . ? C9 N2 Cu 130.6(4) . 3_566 ? N1 N2 Cu 122.1(4) . 3_566 ? C8 N3 C9 104.9(5) . . ? C8 N3 N4 133.4(5) . . ? C9 N3 N4 121.6(6) . . ? C1 N4 N3 114.5(5) . . ? N4 C1 C2 119.0(6) . . ? N4 C1 H1A 120.5 . . ? C2 C1 H1A 120.5 . . ? C3 C2 C7 120.0(6) . . ? C3 C2 C1 123.3(6) . . ? C7 C2 C1 116.7(6) . . ? C4 C3 C2 120.6(6) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C3 C4 C5 119.6(7) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C6 C5 C4 120.7(6) . . ? C6 C5 Cl5 118.8(6) . . ? C4 C5 Cl5 120.5(6) . . ? C5 C6 C7 120.2(6) . . ? C5 C6 H6A 119.9 . . ? C7 C6 H6A 119.9 . . ? C6 C7 C2 118.8(6) . . ? C6 C7 H7A 120.6 . . ? C2 C7 H7A 120.6 . . ? N1 C8 N3 110.4(6) . . ? N1 C8 H8A 124.8 . . ? N3 C8 H8A 124.8 . . ? N2 C9 N3 110.7(6) . . ? N2 C9 H9A 124.6 . . ? N3 C9 H9A 124.6 . . ? C18 N11 N12 108.6(5) . . ? C18 N11 Cu 129.6(5) . . ? N12 N11 Cu 121.7(4) . . ? C19 N12 N11 105.5(5) . . ? C18 N13 C19 105.7(5) . . ? C18 N13 N14 132.4(6) . . ? C19 N13 N14 121.9(6) . . ? C11 N14 N13 118.1(6) . . ? N14 C11 C12 121.0(6) . . ? N14 C11 H11A 119.5 . . ? C12 C11 H11A 119.5 . . ? C17 C12 C13 119.2(6) . . ? C17 C12 C11 119.5(6) . . ? C13 C12 C11 121.2(6) . . ? C12 C13 C14 119.8(6) . . ? C12 C13 H13A 120.1 . . ? C14 C13 H13A 120.1 . . ? C15 C14 C13 118.0(7) . . ? C15 C14 H14A 121.0 . . ? C13 C14 H14A 121.0 . . ? C16 C15 C14 123.9(6) . . ? C16 C15 Cl15 118.8(5) . . ? C14 C15 Cl15 117.3(6) . . ? C15 C16 C17 117.7(6) . . ? C15 C16 H16A 121.2 . . ? C17 C16 H16A 121.2 . . ? C12 C17 C16 121.4(7) . . ? C12 C17 H17A 119.3 . . ? C16 C17 H17A 119.3 . . ? N11 C18 N13 109.7(6) . . ? N11 C18 H18A 125.1 . . ? N13 C18 H18A 125.1 . . ? N12 C19 N13 110.5(6) . . ? N12 C19 H19A 124.8 . . ? N13 C19 H19A 124.8 . . ? C26 C21 C22 118.2(6) . . ? C26 C21 C27 120.8(6) . . ? C22 C21 C27 121.0(7) . . ? C21 C22 C23 120.3(7) . . ? C21 C22 H22A 119.8 . . ? C23 C22 H22A 119.8 . . ? C24 C23 C22 120.0(7) . . ? C24 C23 H23A 120.0 . . ? C22 C23 H23A 120.0 . . ? C25 C24 C23 119.8(7) . . ? C25 C24 H24A 120.1 . . ? C23 C24 H24A 120.1 . . ? C24 C25 C26 120.8(7) . . ? C24 C25 H25A 119.6 . . ? C26 C25 H25A 119.6 . . ? C21 C26 C25 120.9(6) . . ? C21 C26 H26A 119.6 . . ? C25 C26 H26A 119.6 . . ? C21 C27 H27A 109.5 . . ? C21 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C21 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 N2 C9 0.6(6) . . . . ? Cu N1 N2 C9 -179.4(4) . . . . ? C8 N1 N2 Cu 171.3(3) . . . 3_566 ? Cu N1 N2 Cu -8.7(5) . . . 3_566 ? C8 N3 N4 C1 2.0(9) . . . . ? C9 N3 N4 C1 -174.7(5) . . . . ? N3 N4 C1 C2 179.7(5) . . . . ? N4 C1 C2 C3 0.6(9) . . . . ? N4 C1 C2 C7 -178.7(5) . . . . ? C7 C2 C3 C4 -1.1(9) . . . . ? C1 C2 C3 C4 179.7(5) . . . . ? C2 C3 C4 C5 1.9(9) . . . . ? C3 C4 C5 C6 -2.1(9) . . . . ? C3 C4 C5 Cl5 177.1(5) . . . . ? C4 C5 C6 C7 1.5(9) . . . . ? Cl5 C5 C6 C7 -177.7(4) . . . . ? C5 C6 C7 C2 -0.7(9) . . . . ? C3 C2 C7 C6 0.5(9) . . . . ? C1 C2 C7 C6 179.8(5) . . . . ? N2 N1 C8 N3 -0.7(6) . . . . ? Cu N1 C8 N3 179.3(4) . . . . ? C9 N3 C8 N1 0.5(6) . . . . ? N4 N3 C8 N1 -176.7(5) . . . . ? N1 N2 C9 N3 -0.3(6) . . . . ? Cu N2 C9 N3 -169.9(3) 3_566 . . . ? C8 N3 C9 N2 -0.1(6) . . . . ? N4 N3 C9 N2 177.5(5) . . . . ? C18 N11 N12 C19 0.1(7) . . . . ? Cu N11 N12 C19 -176.5(4) . . . . ? C18 N13 N14 C11 -4.1(9) . . . . ? C19 N13 N14 C11 175.3(5) . . . . ? N13 N14 C11 C12 178.3(5) . . . . ? N14 C11 C12 C17 179.2(5) . . . . ? N14 C11 C12 C13 1.3(9) . . . . ? C17 C12 C13 C14 0.6(9) . . . . ? C11 C12 C13 C14 178.4(5) . . . . ? C12 C13 C14 C15 0.0(9) . . . . ? C13 C14 C15 C16 -0.4(9) . . . . ? C13 C14 C15 Cl15 -179.5(4) . . . . ? C14 C15 C16 C17 0.0(9) . . . . ? Cl15 C15 C16 C17 179.1(4) . . . . ? C13 C12 C17 C16 -1.0(9) . . . . ? C11 C12 C17 C16 -178.8(5) . . . . ? C15 C16 C17 C12 0.7(9) . . . . ? N12 N11 C18 N13 -1.1(7) . . . . ? Cu N11 C18 N13 175.3(4) . . . . ? C19 N13 C18 N11 1.5(7) . . . . ? N14 N13 C18 N11 -179.0(5) . . . . ? N11 N12 C19 N13 0.8(7) . . . . ? C18 N13 C19 N12 -1.4(7) . . . . ? N14 N13 C19 N12 179.0(5) . . . . ? C26 C21 C22 C23 0.6(11) . . . . ? C27 C21 C22 C23 -178.1(7) . . . . ? C21 C22 C23 C24 -1.6(12) . . . . ? C22 C23 C24 C25 1.9(12) . . . . ? C23 C24 C25 C26 -1.2(11) . . . . ? C22 C21 C26 C25 0.1(11) . . . . ? C27 C21 C26 C25 178.8(6) . . . . ? C24 C25 C26 C21 0.2(11) . . . . ? _refine_diff_density_max 0.446 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.109 _database_code_depnum_ccdc_archive 'CCDC 949082' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1-o-C8H10 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; bis(\m~2~-4-(E)-(4-chlorobenzylidene)amino-4H-1,2,4-triazole)-bis((E)-4-(chlor obenzylidene)amino-4H-1,2,4-triazole)-di-copper(i) diperchlorate o-xylene disolvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H28 Cl4 Cu2 N16, 2(Cl O4), 2(C8 H10) ' _chemical_formula_sum 'C52 H48 Cl6 Cu2 N16 O8' _chemical_formula_weight 1364.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.183(3) _cell_length_b 18.048(3) _cell_length_c 22.365(4) _cell_angle_alpha 90 _cell_angle_beta 95.08(3) _cell_angle_gamma 90 _cell_volume 5702.4(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9157 _cell_measurement_theta_min 2.8642 _cell_measurement_theta_max 28.7248 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.590 _exptl_crystal_F_000 2784 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_absorpt_coefficient_mu 1.096 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_T_min 0.792 _exptl_absorpt_correction_T_max 0.911 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 37162 _diffrn_reflns_av_unetI/netI 0.0992 _diffrn_reflns_av_R_equivalents 0.0644 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.871 _diffrn_reflns_theta_max 27.000 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_point_group_measured_fraction_full 0.995 _reflns_number_total 12342 _reflns_number_gt 6587 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_structure_solution ; SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.) ; _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0352P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 12342 _refine_ls_number_parameters 785 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1009 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.0831 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 0.813 _refine_ls_restrained_S_all 0.813 _refine_ls_shift/su_max 0.005 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.23558(3) 0.41553(2) 0.05155(2) 0.02109(10) Uani 1 1 d . . . . . Cu2 Cu 0.27032(3) 0.55899(2) -0.05126(2) 0.01998(10) Uani 1 1 d . . . . . Cl1 Cl 0.19319(7) 0.46354(5) 0.27663(4) 0.0336(2) Uani 1 1 d . . . . . O1 O 0.1759(2) 0.52235(13) 0.31535(11) 0.0552(8) Uani 1 1 d . . . . . O2 O 0.2185(4) 0.39728(16) 0.31154(15) 0.0418(14) Uani 0.848(12) 1 d . . P A 1 O3 O 0.1176(3) 0.4467(4) 0.23303(16) 0.0496(15) Uani 0.848(12) 1 d . . P A 1 O4 O 0.2752(3) 0.4845(3) 0.2446(2) 0.0397(12) Uani 0.848(12) 1 d . . P A 1 O21 O 0.154(2) 0.4009(11) 0.3050(9) 0.046(7) Uani 0.152(12) 1 d . U P A 2 O31 O 0.0906(14) 0.4886(13) 0.2399(8) 0.027(6) Uani 0.152(12) 1 d . U P A 2 O41 O 0.2486(19) 0.4582(14) 0.2335(11) 0.029(6) Uani 0.152(12) 1 d . U P A 2 Cl2 Cl 0.33074(6) 0.98634(4) 0.22029(4) 0.0270(2) Uani 1 1 d . . . . . O5 O 0.25446(17) 0.96783(14) 0.25575(11) 0.0504(7) Uani 1 1 d . . . . . O6 O 0.36025(19) 0.92209(12) 0.18919(11) 0.0474(7) Uani 1 1 d . . . . . O7 O 0.30029(16) 1.04324(12) 0.17840(10) 0.0348(6) Uani 1 1 d . . . . . O8 O 0.40940(16) 1.01283(13) 0.26002(10) 0.0378(6) Uani 1 1 d . . . . . N1 N 0.20502(17) 0.51707(13) 0.06939(11) 0.0205(6) Uani 1 1 d . . . . . N2 N 0.21441(17) 0.57429(13) 0.02785(11) 0.0205(6) Uani 1 1 d . . . . . N3 N 0.16964(17) 0.62216(13) 0.11051(11) 0.0186(6) Uani 1 1 d . . . . . N4 N 0.14531(17) 0.67932(14) 0.14863(12) 0.0220(6) Uani 1 1 d . . . . . C1 C 0.1296(2) 0.66047(17) 0.20175(14) 0.0224(7) Uani 1 1 d . . . . . H1A H 0.1339 0.6098 0.2132 0.027 Uiso 1 1 calc R U . . . C2 C 0.1049(2) 0.71595(17) 0.24519(14) 0.0208(7) Uani 1 1 d . . . . . C3 C 0.0991(2) 0.79149(17) 0.23194(14) 0.0231(8) Uani 1 1 d . . . . . H3A H 0.1108 0.8084 0.1930 0.028 Uiso 1 1 calc R U . . . C4 C 0.0766(2) 0.84159(17) 0.27468(15) 0.0262(8) Uani 1 1 d . . . . . H4A H 0.0734 0.8930 0.2657 0.031 Uiso 1 1 calc R U . . . C5 C 0.0587(2) 0.81649(18) 0.33092(15) 0.0238(8) Uani 1 1 d . . . . . Cl5 Cl 0.03289(6) 0.87887(5) 0.38689(4) 0.0321(2) Uani 1 1 d . . . . . C6 C 0.0625(2) 0.74228(18) 0.34506(15) 0.0263(8) Uani 1 1 d . . . . . H6A H 0.0494 0.7258 0.3838 0.032 Uiso 1 1 calc R U . . . C7 C 0.0859(2) 0.69180(18) 0.30184(15) 0.0255(8) Uani 1 1 d . . . . . H7A H 0.0888 0.6404 0.3111 0.031 Uiso 1 1 calc R U . . . C8 C 0.1777(2) 0.54721(17) 0.11829(14) 0.0214(7) Uani 1 1 d . . . . . H8A H 0.1654 0.5211 0.1536 0.026 Uiso 1 1 calc R U . . . C9 C 0.1925(2) 0.63597(17) 0.05406(13) 0.0200(7) Uani 1 1 d . . . . . H9A H 0.1925 0.6836 0.0360 0.024 Uiso 1 1 calc R U . . . N11 N 0.30212(17) 0.45716(13) -0.06826(11) 0.0180(6) Uani 1 1 d . . . . . N12 N 0.29306(17) 0.40078(13) -0.02649(11) 0.0196(6) Uani 1 1 d . . . . . N13 N 0.33899(17) 0.35203(13) -0.10850(11) 0.0174(6) Uani 1 1 d . . . . . N14 N 0.36286(17) 0.29363(13) -0.14601(11) 0.0192(6) Uani 1 1 d . . . . . C11 C 0.3764(2) 0.31254(16) -0.19957(14) 0.0194(7) Uani 1 1 d . . . . . H11A H 0.3699 0.3632 -0.2108 0.023 Uiso 1 1 calc R U . . . C12 C 0.4015(2) 0.25850(16) -0.24386(14) 0.0182(7) Uani 1 1 d . . . . . C13 C 0.4116(2) 0.18282(16) -0.23173(14) 0.0220(7) Uani 1 1 d . . . . . H13A H 0.4024 0.1646 -0.1928 0.026 Uiso 1 1 calc R U . . . C14 C 0.4349(2) 0.13429(17) -0.27581(14) 0.0224(7) Uani 1 1 d . . . . . H14A H 0.4432 0.0830 -0.2674 0.027 Uiso 1 1 calc R U . . . C15 C 0.4458(2) 0.16197(16) -0.33282(14) 0.0206(7) Uani 1 1 d . . . . . Cl15 Cl 0.47012(6) 0.10092(4) -0.38972(4) 0.0274(2) Uani 1 1 d . . . . . C16 C 0.4371(2) 0.23664(16) -0.34601(14) 0.0195(7) Uani 1 1 d . . . . . H16A H 0.4464 0.2545 -0.3850 0.023 Uiso 1 1 calc R U . . . C17 C 0.4146(2) 0.28485(17) -0.30122(14) 0.0225(8) Uani 1 1 d . . . . . H17A H 0.4081 0.3363 -0.3096 0.027 Uiso 1 1 calc R U . . . C18 C 0.3297(2) 0.42597(16) -0.11701(14) 0.0194(7) Uani 1 1 d . . . . . H18A H 0.3413 0.4515 -0.1528 0.023 Uiso 1 1 calc R U . . . C19 C 0.3158(2) 0.33873(17) -0.05219(13) 0.0186(7) Uani 1 1 d . . . . . H19A H 0.3158 0.2913 -0.0338 0.022 Uiso 1 1 calc R U . . . N21 N 0.21841(17) 0.32179(13) 0.09120(12) 0.0217(6) Uani 1 1 d . . . . . N22 N 0.22891(19) 0.25268(14) 0.06400(12) 0.0259(7) Uani 1 1 d . . . . . N23 N 0.18780(18) 0.23720(14) 0.15592(11) 0.0222(6) Uani 1 1 d . . . . . N24 N 0.16319(18) 0.19579(14) 0.20491(12) 0.0246(6) Uani 1 1 d . . . . . C21 C 0.1517(2) 0.23218(17) 0.25274(15) 0.0228(8) Uani 1 1 d . . . . . H21A H 0.1609 0.2843 0.2539 0.027 Uiso 1 1 calc R U . . . C22 C 0.1245(2) 0.19301(17) 0.30524(14) 0.0208(7) Uani 1 1 d . . . . . C23 C 0.1116(2) 0.11632(17) 0.30441(15) 0.0254(8) Uani 1 1 d . . . . . H23A H 0.1206 0.0890 0.2691 0.031 Uiso 1 1 calc R U . . . C24 C 0.0857(2) 0.08010(18) 0.35493(15) 0.0272(8) Uani 1 1 d . . . . . H24A H 0.0762 0.0280 0.3545 0.033 Uiso 1 1 calc R U . . . C25 C 0.0740(2) 0.12081(18) 0.40611(14) 0.0245(8) Uani 1 1 d . . . . . Cl25 Cl 0.04279(6) 0.07479(5) 0.46978(4) 0.0319(2) Uani 1 1 d . . . . . C26 C 0.0861(2) 0.19680(18) 0.40812(15) 0.0253(8) Uani 1 1 d . . . . . H26A H 0.0769 0.2238 0.4436 0.030 Uiso 1 1 calc R U . . . C27 C 0.1119(2) 0.23269(18) 0.35739(15) 0.0264(8) Uani 1 1 d . . . . . H27A H 0.1212 0.2848 0.3581 0.032 Uiso 1 1 calc R U . . . C28 C 0.1943(2) 0.31120(16) 0.14566(15) 0.0216(7) Uani 1 1 d . . . . . H28A H 0.1832 0.3492 0.1736 0.026 Uiso 1 1 calc R U . . . C29 C 0.2094(2) 0.20372(18) 0.10438(14) 0.0253(8) Uani 1 1 d . . . . . H29A H 0.2102 0.1516 0.0984 0.030 Uiso 1 1 calc R U . . . N31 N 0.28439(17) 0.65227(13) -0.09274(11) 0.0191(6) Uani 1 1 d . . . . . N32 N 0.29002(19) 0.71837(14) -0.06089(12) 0.0271(7) Uani 1 1 d . . . . . N33 N 0.31732(17) 0.73907(13) -0.15484(11) 0.0195(6) Uani 1 1 d . . . . . N34 N 0.33948(18) 0.78346(13) -0.20298(11) 0.0204(6) Uani 1 1 d . . . . . C31 C 0.3485(2) 0.75001(16) -0.25254(14) 0.0188(7) Uani 1 1 d . . . . . H31A H 0.3395 0.6979 -0.2556 0.023 Uiso 1 1 calc R U . . . C32 C 0.3728(2) 0.79282(16) -0.30447(14) 0.0176(7) Uani 1 1 d . . . . . C33 C 0.3887(2) 0.86894(16) -0.30114(13) 0.0206(7) Uani 1 1 d . . . . . H33A H 0.3827 0.8942 -0.2644 0.025 Uiso 1 1 calc R U . . . C34 C 0.4129(2) 0.90829(16) -0.35042(14) 0.0205(7) Uani 1 1 d . . . . . H34A H 0.4236 0.9602 -0.3479 0.025 Uiso 1 1 calc R U . . . C35 C 0.4212(2) 0.87070(17) -0.40369(13) 0.0197(7) Uani 1 1 d . . . . . Cl35 Cl 0.45308(5) 0.91984(4) -0.46609(3) 0.02388(19) Uani 1 1 d . . . . . C36 C 0.4064(2) 0.79521(16) -0.40847(14) 0.0209(7) Uani 1 1 d . . . . . H36A H 0.4126 0.7703 -0.4454 0.025 Uiso 1 1 calc R U . . . C37 C 0.3824(2) 0.75654(16) -0.35878(14) 0.0202(7) Uani 1 1 d . . . . . H37A H 0.3723 0.7046 -0.3615 0.024 Uiso 1 1 calc R U . . . C38 C 0.3001(2) 0.66578(16) -0.14840(14) 0.0202(7) Uani 1 1 d . . . . . H38A H 0.2994 0.6299 -0.1795 0.024 Uiso 1 1 calc R U . . . C39 C 0.3109(2) 0.76894(18) -0.09961(15) 0.0278(8) Uani 1 1 d . . . . . H39A H 0.3203 0.8199 -0.0903 0.033 Uiso 1 1 calc R U . . . C41 C 0.4051(2) 0.56716(17) 0.47255(16) 0.0288(8) Uani 1 1 d . . . . . C42 C 0.4660(2) 0.56890(17) 0.42585(15) 0.0288(8) Uani 1 1 d . . . . . C43 C 0.5541(3) 0.60273(18) 0.43627(16) 0.0348(9) Uani 1 1 d . . . . . H43A H 0.5958 0.6030 0.4053 0.042 Uiso 1 1 calc R U . . . C44 C 0.5825(3) 0.63646(18) 0.49148(16) 0.0360(9) Uani 1 1 d . . . . . H44A H 0.6423 0.6603 0.4977 0.043 Uiso 1 1 calc R U . . . C45 C 0.5225(3) 0.63438(19) 0.53631(16) 0.0372(9) Uani 1 1 d . . . . . H45A H 0.5407 0.6573 0.5738 0.045 Uiso 1 1 calc R U . . . C46 C 0.4360(3) 0.59932(18) 0.52738(16) 0.0333(9) Uani 1 1 d . . . . . H46A H 0.3965 0.5971 0.5595 0.040 Uiso 1 1 calc R U . . . C47 C 0.3101(2) 0.52993(19) 0.46314(16) 0.0400(10) Uani 1 1 d . . . . . H47A H 0.2773 0.5342 0.4998 0.060 Uiso 1 1 calc R U . . . H47B H 0.3188 0.4775 0.4538 0.060 Uiso 1 1 calc R U . . . H47C H 0.2722 0.5538 0.4298 0.060 Uiso 1 1 calc R U . . . C48 C 0.4368(3) 0.53384(19) 0.36618(15) 0.0400(9) Uani 1 1 d . . . . . H48A H 0.4874 0.5401 0.3395 0.060 Uiso 1 1 calc R U . . . H48B H 0.3789 0.5577 0.3483 0.060 Uiso 1 1 calc R U . . . H48C H 0.4250 0.4809 0.3718 0.060 Uiso 1 1 calc R U . . . C51 C -0.0065(2) 0.9033(2) 0.04503(16) 0.0358(9) Uani 1 1 d . . . . . C52 C 0.0665(3) 0.9309(2) 0.08545(16) 0.0365(9) Uani 1 1 d . . . . . C53 C 0.1567(3) 0.9004(2) 0.08571(16) 0.0375(9) Uani 1 1 d . . . . . H53A H 0.2062 0.9184 0.1133 0.045 Uiso 1 1 calc R U . . . C54 C 0.1757(3) 0.84367(19) 0.04612(16) 0.0373(9) Uani 1 1 d . . . . . H54A H 0.2373 0.8229 0.0470 0.045 Uiso 1 1 calc R U . . . C55 C 0.1042(3) 0.8182(2) 0.00592(16) 0.0399(10) Uani 1 1 d . . . . . H55A H 0.1164 0.7806 -0.0222 0.048 Uiso 1 1 calc R U . . . C56 C 0.0148(3) 0.8476(2) 0.00678(17) 0.0398(10) Uani 1 1 d . . . . . H56A H -0.0344 0.8284 -0.0204 0.048 Uiso 1 1 calc R U . . . C57 C -0.1049(3) 0.9350(2) 0.04334(18) 0.0537(12) Uani 1 1 d . . . . . H57A H -0.1461 0.9096 0.0123 0.081 Uiso 1 1 calc R U . . . H57B H -0.1030 0.9880 0.0341 0.081 Uiso 1 1 calc R U . . . H57C H -0.1297 0.9280 0.0825 0.081 Uiso 1 1 calc R U . . . C58 C 0.0497(3) 0.9944(2) 0.12805(18) 0.0569(12) Uani 1 1 d . . . . . H58A H 0.1085 1.0054 0.1528 0.085 Uiso 1 1 calc R U . . . H58B H 0.0005 0.9803 0.1540 0.085 Uiso 1 1 calc R U . . . H58C H 0.0293 1.0384 0.1048 0.085 Uiso 1 1 calc R U . . . 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 0.0274(2) 0.0196(2) 0.0169(2) 0.00116(17) 0.00581(18) 0.00010(18) Cu2 0.0251(2) 0.0181(2) 0.0173(2) 0.00085(17) 0.00481(17) -0.00054(17) Cl1 0.0494(6) 0.0284(5) 0.0230(5) -0.0001(4) 0.0037(4) -0.0068(4) O1 0.087(2) 0.0385(16) 0.0400(17) -0.0088(13) 0.0045(15) 0.0245(15) O2 0.059(4) 0.0215(17) 0.047(2) 0.0149(14) 0.016(2) 0.0027(17) O3 0.039(2) 0.073(4) 0.036(2) -0.002(2) -0.0065(17) -0.020(2) O4 0.036(2) 0.042(3) 0.043(3) 0.009(2) 0.0126(19) -0.0110(19) O21 0.054(12) 0.040(9) 0.043(9) 0.013(7) 0.011(8) -0.011(8) O31 0.028(8) 0.028(9) 0.024(8) 0.012(7) 0.004(6) -0.010(7) O41 0.038(10) 0.033(10) 0.019(8) 0.015(7) 0.010(7) 0.005(7) Cl2 0.0367(5) 0.0197(4) 0.0242(5) 0.0001(4) 0.0010(4) 0.0010(4) O5 0.0394(16) 0.0628(18) 0.0508(18) 0.0248(14) 0.0139(14) -0.0031(14) O6 0.0674(19) 0.0240(13) 0.0487(18) -0.0176(12) -0.0065(14) 0.0128(13) O7 0.0395(15) 0.0265(13) 0.0372(15) 0.0149(11) -0.0033(12) 0.0027(11) O8 0.0378(15) 0.0415(15) 0.0322(15) -0.0166(12) -0.0079(12) 0.0067(12) N1 0.0241(15) 0.0201(14) 0.0177(15) 0.0021(12) 0.0041(12) -0.0012(11) N2 0.0217(15) 0.0214(15) 0.0186(15) 0.0009(12) 0.0027(12) -0.0029(12) N3 0.0202(15) 0.0184(15) 0.0172(15) -0.0045(12) 0.0016(12) -0.0014(11) N4 0.0219(15) 0.0255(15) 0.0189(16) -0.0060(12) 0.0040(12) 0.0004(12) C1 0.0222(19) 0.0240(18) 0.0206(19) -0.0066(15) -0.0002(15) 0.0003(14) C2 0.0188(18) 0.0246(18) 0.0188(19) -0.0059(14) 0.0014(14) 0.0011(14) C3 0.0216(18) 0.029(2) 0.0195(19) -0.0007(15) 0.0027(15) -0.0006(15) C4 0.030(2) 0.0186(18) 0.030(2) -0.0033(15) 0.0037(16) -0.0013(15) C5 0.0209(19) 0.029(2) 0.022(2) -0.0100(15) 0.0028(15) -0.0028(15) Cl5 0.0347(5) 0.0327(5) 0.0301(5) -0.0141(4) 0.0097(4) -0.0008(4) C6 0.027(2) 0.033(2) 0.019(2) -0.0009(15) 0.0058(15) 0.0003(16) C7 0.027(2) 0.0242(19) 0.026(2) -0.0027(15) 0.0055(16) 0.0033(15) C8 0.0225(18) 0.0235(19) 0.0189(19) 0.0001(15) 0.0055(14) -0.0047(14) C9 0.0222(18) 0.0211(18) 0.0169(18) -0.0002(14) 0.0033(14) -0.0024(14) N11 0.0212(15) 0.0166(14) 0.0164(15) 0.0022(11) 0.0034(12) -0.0011(11) N12 0.0218(15) 0.0182(14) 0.0197(15) 0.0025(12) 0.0063(12) -0.0001(11) N13 0.0205(15) 0.0141(14) 0.0182(15) -0.0008(11) 0.0043(12) -0.0001(11) N14 0.0233(15) 0.0173(14) 0.0171(15) -0.0054(12) 0.0017(12) 0.0021(11) C11 0.0204(18) 0.0160(16) 0.0219(19) 0.0007(14) 0.0019(15) -0.0001(13) C12 0.0148(17) 0.0188(17) 0.0210(19) -0.0035(14) 0.0018(14) 0.0009(13) C13 0.0278(19) 0.0208(18) 0.0174(19) 0.0024(14) 0.0032(15) 0.0001(14) C14 0.0293(19) 0.0176(17) 0.0210(19) -0.0018(14) 0.0049(15) 0.0002(14) C15 0.0201(18) 0.0212(18) 0.0206(19) -0.0077(14) 0.0031(15) -0.0042(14) Cl15 0.0365(5) 0.0230(4) 0.0238(5) -0.0070(3) 0.0088(4) -0.0003(4) C16 0.0209(18) 0.0228(18) 0.0151(18) 0.0002(14) 0.0033(14) -0.0025(14) C17 0.0234(19) 0.0184(17) 0.025(2) 0.0004(14) 0.0001(15) -0.0005(14) C18 0.0242(18) 0.0230(18) 0.0112(17) -0.0012(14) 0.0016(14) 0.0007(14) C19 0.0225(18) 0.0201(17) 0.0132(17) 0.0002(13) 0.0016(14) -0.0021(14) N21 0.0227(15) 0.0202(15) 0.0229(17) 0.0028(12) 0.0060(13) 0.0022(12) N22 0.0315(17) 0.0197(15) 0.0262(17) -0.0021(12) 0.0009(13) -0.0011(13) N23 0.0237(16) 0.0241(15) 0.0195(16) 0.0031(12) 0.0049(12) 0.0017(12) N24 0.0248(16) 0.0284(16) 0.0213(17) 0.0120(13) 0.0066(13) -0.0010(12) C21 0.0212(19) 0.0219(18) 0.025(2) 0.0053(15) 0.0025(15) -0.0020(14) C22 0.0155(17) 0.0250(18) 0.022(2) 0.0064(14) 0.0003(14) -0.0003(14) C23 0.029(2) 0.0231(18) 0.024(2) 0.0053(15) 0.0065(16) 0.0022(15) C24 0.030(2) 0.0225(18) 0.030(2) 0.0077(16) 0.0084(16) 0.0031(15) C25 0.0150(18) 0.032(2) 0.027(2) 0.0155(16) 0.0037(15) 0.0004(14) Cl25 0.0262(5) 0.0444(5) 0.0255(5) 0.0163(4) 0.0039(4) -0.0021(4) C26 0.025(2) 0.032(2) 0.0186(19) 0.0040(15) 0.0012(15) -0.0014(15) C27 0.029(2) 0.0245(19) 0.025(2) 0.0028(15) -0.0009(16) 0.0010(15) C28 0.0248(19) 0.0161(17) 0.025(2) 0.0022(14) 0.0076(15) 0.0018(14) C29 0.031(2) 0.0243(19) 0.0204(19) 0.0010(15) 0.0025(16) -0.0066(15) N31 0.0218(15) 0.0172(14) 0.0185(15) -0.0009(12) 0.0026(12) -0.0008(11) N32 0.0409(19) 0.0179(15) 0.0235(17) -0.0029(12) 0.0092(14) -0.0040(13) N33 0.0234(15) 0.0165(14) 0.0189(16) 0.0010(12) 0.0045(12) -0.0015(11) N34 0.0270(16) 0.0154(14) 0.0190(16) 0.0039(12) 0.0034(12) -0.0004(11) C31 0.0201(18) 0.0153(16) 0.0203(19) 0.0036(14) -0.0021(14) -0.0010(13) C32 0.0160(17) 0.0177(16) 0.0192(19) 0.0008(14) 0.0017(14) 0.0004(13) C33 0.0248(19) 0.0234(18) 0.0140(18) -0.0025(14) 0.0038(14) 0.0020(14) C34 0.0232(18) 0.0171(17) 0.0211(19) 0.0003(14) 0.0004(15) -0.0008(14) C35 0.0177(17) 0.0246(18) 0.0169(18) 0.0072(14) 0.0021(14) 0.0010(14) Cl35 0.0248(5) 0.0297(4) 0.0174(4) 0.0070(3) 0.0034(4) -0.0019(4) C36 0.0240(19) 0.0217(18) 0.0171(19) -0.0013(14) 0.0017(15) 0.0019(14) C37 0.0201(18) 0.0164(16) 0.024(2) 0.0011(14) 0.0013(15) -0.0010(13) C38 0.0214(18) 0.0192(17) 0.0204(19) 0.0005(14) 0.0041(14) 0.0020(14) C39 0.045(2) 0.0173(18) 0.022(2) -0.0030(15) 0.0045(17) -0.0013(16) C41 0.030(2) 0.0190(18) 0.037(2) 0.0050(15) 0.0010(17) 0.0080(15) C42 0.037(2) 0.0197(18) 0.030(2) 0.0043(15) 0.0046(17) 0.0073(15) C43 0.040(2) 0.029(2) 0.036(2) 0.0105(17) 0.0044(19) -0.0007(17) C44 0.040(2) 0.026(2) 0.041(2) 0.0053(17) 0.0010(19) 0.0019(17) C45 0.050(3) 0.026(2) 0.034(2) -0.0104(17) 0.001(2) 0.0047(18) C46 0.040(2) 0.030(2) 0.030(2) -0.0006(16) 0.0027(18) 0.0093(17) C47 0.038(2) 0.034(2) 0.049(3) 0.0025(18) 0.0049(19) -0.0002(18) C48 0.050(2) 0.039(2) 0.032(2) -0.0013(18) 0.0072(19) 0.0005(19) C51 0.032(2) 0.047(2) 0.028(2) 0.0040(18) 0.0028(18) 0.0024(18) C52 0.036(2) 0.043(2) 0.032(2) 0.0018(18) 0.0053(18) -0.0001(18) C53 0.035(2) 0.044(2) 0.033(2) 0.0007(18) -0.0004(18) -0.0048(18) C54 0.033(2) 0.038(2) 0.040(2) 0.0062(18) -0.0002(18) 0.0041(18) C55 0.039(2) 0.043(2) 0.036(2) -0.0049(18) -0.0071(19) 0.0067(19) C56 0.034(2) 0.045(2) 0.039(2) -0.0027(19) -0.0033(19) -0.0062(19) C57 0.039(2) 0.077(3) 0.045(3) -0.004(2) 0.002(2) 0.002(2) C58 0.048(3) 0.075(3) 0.047(3) -0.018(2) 0.001(2) 0.004(2) _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 N1 1.933(2) . ? Cu1 N21 1.935(2) . ? Cu1 N12 2.008(2) . ? Cu2 N11 1.938(2) . ? Cu2 N31 1.941(2) . ? Cu2 N2 2.021(3) . ? Cl1 O41 1.30(2) . ? Cl1 O1 1.405(2) . ? Cl1 O3 1.416(3) . ? Cl1 O21 1.430(19) . ? Cl1 O2 1.456(3) . ? Cl1 O4 1.469(4) . ? Cl1 O31 1.67(2) . ? Cl2 O7 1.431(2) . ? Cl2 O6 1.434(2) . ? Cl2 O5 1.436(2) . ? Cl2 O8 1.445(2) . ? N1 C8 1.310(4) . ? N1 N2 1.403(3) . ? N2 C9 1.308(4) . ? N3 C9 1.354(3) . ? N3 C8 1.367(4) . ? N3 N4 1.401(3) . ? N4 C1 1.274(4) . ? C1 C2 1.459(4) . ? C1 H1A 0.9500 . ? C2 C7 1.389(4) . ? C2 C3 1.396(4) . ? C3 C4 1.374(4) . ? C3 H3A 0.9500 . ? C4 C5 1.382(4) . ? C4 H4A 0.9500 . ? C5 C6 1.376(4) . ? C5 Cl5 1.746(3) . ? C6 C7 1.390(4) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? N11 C18 1.317(4) . ? N11 N12 1.395(3) . ? N12 C19 1.312(4) . ? N13 C19 1.351(3) . ? N13 C18 1.353(3) . ? N13 N14 1.407(3) . ? N14 C11 1.276(4) . ? C11 C12 1.457(4) . ? C11 H11A 0.9500 . ? C12 C17 1.396(4) . ? C12 C13 1.397(4) . ? C13 C14 1.380(4) . ? C13 H13A 0.9500 . ? C14 C15 1.391(4) . ? C14 H14A 0.9500 . ? C15 C16 1.383(4) . ? C15 Cl15 1.741(3) . ? C16 C17 1.385(4) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? N21 C28 1.308(4) . ? N21 N22 1.402(3) . ? N22 C29 1.311(4) . ? N23 C28 1.360(4) . ? N23 C29 1.360(4) . ? N23 N24 1.396(3) . ? N24 C21 1.278(4) . ? C21 C22 1.452(4) . ? C21 H21A 0.9500 . ? C22 C27 1.394(4) . ? C22 C23 1.396(4) . ? C23 C24 1.383(4) . ? C23 H23A 0.9500 . ? C24 C25 1.383(4) . ? C24 H24A 0.9500 . ? C25 C26 1.382(4) . ? C25 Cl25 1.739(3) . ? C26 C27 1.384(4) . ? C26 H26A 0.9500 . ? C27 H27A 0.9500 . ? C28 H28A 0.9500 . ? C29 H29A 0.9500 . ? N31 C38 1.307(4) . ? N31 N32 1.388(3) . ? N32 C39 1.310(4) . ? N33 C38 1.355(4) . ? N33 C39 1.358(4) . ? N33 N34 1.400(3) . ? N34 C31 1.278(4) . ? C31 C32 1.461(4) . ? C31 H31A 0.9500 . ? C32 C33 1.393(4) . ? C32 C37 1.397(4) . ? C33 C34 1.380(4) . ? C33 H33A 0.9500 . ? C34 C35 1.385(4) . ? C34 H34A 0.9500 . ? C35 C36 1.381(4) . ? C35 Cl35 1.746(3) . ? C36 C37 1.380(4) . ? C36 H36A 0.9500 . ? C37 H37A 0.9500 . ? C38 H38A 0.9500 . ? C39 H39A 0.9500 . ? C41 C46 1.392(5) . ? C41 C42 1.414(4) . ? C41 C47 1.503(4) . ? C42 C43 1.391(5) . ? C42 C48 1.502(4) . ? C43 C44 1.404(5) . ? C43 H43A 0.9500 . ? C44 C45 1.372(5) . ? C44 H44A 0.9500 . ? C45 C46 1.379(5) . ? C45 H45A 0.9500 . ? C46 H46A 0.9500 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? C51 C56 1.371(5) . ? C51 C52 1.404(5) . ? C51 C57 1.506(5) . ? C52 C53 1.393(5) . ? C52 C58 1.523(5) . ? C53 C54 1.395(5) . ? C53 H53A 0.9500 . ? C54 C55 1.373(5) . ? C54 H54A 0.9500 . ? C55 C56 1.376(5) . ? C55 H55A 0.9500 . ? C56 H56A 0.9500 . ? C57 H57A 0.9800 . ? C57 H57B 0.9800 . ? C57 H57C 0.9800 . ? C58 H58A 0.9800 . ? C58 H58B 0.9800 . ? C58 H58C 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 N1 Cu1 N21 133.99(11) . . ? N1 Cu1 N12 114.88(10) . . ? N21 Cu1 N12 111.07(10) . . ? N11 Cu2 N31 133.89(10) . . ? N11 Cu2 N2 114.68(10) . . ? N31 Cu2 N2 111.40(10) . . ? O41 Cl1 O1 131.5(12) . . ? O1 Cl1 O3 115.0(3) . . ? O41 Cl1 O21 123.5(12) . . ? O1 Cl1 O21 103.2(9) . . ? O1 Cl1 O2 109.77(17) . . ? O3 Cl1 O2 109.2(2) . . ? O1 Cl1 O4 107.2(3) . . ? O3 Cl1 O4 107.6(2) . . ? O2 Cl1 O4 107.8(3) . . ? O41 Cl1 O31 102.3(12) . . ? O1 Cl1 O31 84.6(9) . . ? O21 Cl1 O31 94.6(13) . . ? O7 Cl2 O6 110.31(15) . . ? O7 Cl2 O5 109.27(15) . . ? O6 Cl2 O5 110.26(16) . . ? O7 Cl2 O8 109.70(14) . . ? O6 Cl2 O8 108.87(15) . . ? O5 Cl2 O8 108.41(15) . . ? C8 N1 N2 107.4(2) . . ? C8 N1 Cu1 130.9(2) . . ? N2 N1 Cu1 121.66(19) . . ? C9 N2 N1 106.8(2) . . ? C9 N2 Cu2 129.5(2) . . ? N1 N2 Cu2 123.14(18) . . ? C9 N3 C8 106.1(2) . . ? C9 N3 N4 121.6(2) . . ? C8 N3 N4 132.3(3) . . ? C1 N4 N3 116.3(3) . . ? N4 C1 C2 120.6(3) . . ? N4 C1 H1A 119.7 . . ? C2 C1 H1A 119.7 . . ? C7 C2 C3 119.2(3) . . ? C7 C2 C1 118.0(3) . . ? C3 C2 C1 122.8(3) . . ? C4 C3 C2 120.5(3) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C3 C4 C5 119.4(3) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? C6 C5 C4 121.4(3) . . ? C6 C5 Cl5 118.0(3) . . ? C4 C5 Cl5 120.6(2) . . ? C5 C6 C7 119.0(3) . . ? C5 C6 H6A 120.5 . . ? C7 C6 H6A 120.5 . . ? C2 C7 C6 120.4(3) . . ? C2 C7 H7A 119.8 . . ? C6 C7 H7A 119.8 . . ? N1 C8 N3 109.4(3) . . ? N1 C8 H8A 125.3 . . ? N3 C8 H8A 125.3 . . ? N2 C9 N3 110.3(3) . . ? N2 C9 H9A 124.8 . . ? N3 C9 H9A 124.8 . . ? C18 N11 N12 107.1(2) . . ? C18 N11 Cu2 131.2(2) . . ? N12 N11 Cu2 121.56(18) . . ? C19 N12 N11 106.8(2) . . ? C19 N12 Cu1 128.9(2) . . ? N11 N12 Cu1 123.64(18) . . ? C19 N13 C18 106.1(2) . . ? C19 N13 N14 120.9(2) . . ? C18 N13 N14 132.9(3) . . ? C11 N14 N13 115.0(2) . . ? N14 C11 C12 121.7(3) . . ? N14 C11 H11A 119.2 . . ? C12 C11 H11A 119.2 . . ? C17 C12 C13 119.4(3) . . ? C17 C12 C11 117.2(3) . . ? C13 C12 C11 123.3(3) . . ? C14 C13 C12 120.6(3) . . ? C14 C13 H13A 119.7 . . ? C12 C13 H13A 119.7 . . ? C13 C14 C15 118.7(3) . . ? C13 C14 H14A 120.7 . . ? C15 C14 H14A 120.7 . . ? C16 C15 C14 122.1(3) . . ? C16 C15 Cl15 118.7(2) . . ? C14 C15 Cl15 119.2(2) . . ? C15 C16 C17 118.7(3) . . ? C15 C16 H16A 120.7 . . ? C17 C16 H16A 120.7 . . ? C16 C17 C12 120.6(3) . . ? C16 C17 H17A 119.7 . . ? C12 C17 H17A 119.7 . . ? N11 C18 N13 109.7(3) . . ? N11 C18 H18A 125.1 . . ? N13 C18 H18A 125.1 . . ? N12 C19 N13 110.3(3) . . ? N12 C19 H19A 124.9 . . ? N13 C19 H19A 124.9 . . ? C28 N21 N22 108.7(2) . . ? C28 N21 Cu1 127.5(2) . . ? N22 N21 Cu1 123.8(2) . . ? C29 N22 N21 105.3(3) . . ? C28 N23 C29 105.6(3) . . ? C28 N23 N24 133.1(3) . . ? C29 N23 N24 121.2(3) . . ? C21 N24 N23 116.2(3) . . ? N24 C21 C22 119.3(3) . . ? N24 C21 H21A 120.3 . . ? C22 C21 H21A 120.3 . . ? C27 C22 C23 119.6(3) . . ? C27 C22 C21 119.3(3) . . ? C23 C22 C21 121.0(3) . . ? C24 C23 C22 120.1(3) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 119.9 . . ? C23 C24 C25 119.0(3) . . ? C23 C24 H24A 120.5 . . ? C25 C24 H24A 120.5 . . ? C26 C25 C24 122.0(3) . . ? C26 C25 Cl25 119.1(3) . . ? C24 C25 Cl25 118.8(2) . . ? C25 C26 C27 118.6(3) . . ? C25 C26 H26A 120.7 . . ? C27 C26 H26A 120.7 . . ? C26 C27 C22 120.6(3) . . ? C26 C27 H27A 119.7 . . ? C22 C27 H27A 119.7 . . ? N21 C28 N23 109.2(3) . . ? N21 C28 H28A 125.4 . . ? N23 C28 H28A 125.4 . . ? N22 C29 N23 111.2(3) . . ? N22 C29 H29A 124.4 . . ? N23 C29 H29A 124.4 . . ? C38 N31 N32 108.8(2) . . ? C38 N31 Cu2 130.6(2) . . ? N32 N31 Cu2 120.26(19) . . ? C39 N32 N31 105.4(3) . . ? C38 N33 C39 105.3(3) . . ? C38 N33 N34 134.1(3) . . ? C39 N33 N34 120.7(2) . . ? C31 N34 N33 116.3(2) . . ? N34 C31 C32 119.2(3) . . ? N34 C31 H31A 120.4 . . ? C32 C31 H31A 120.4 . . ? C33 C32 C37 118.7(3) . . ? C33 C32 C31 121.8(3) . . ? C37 C32 C31 119.4(3) . . ? C34 C33 C32 121.0(3) . . ? C34 C33 H33A 119.5 . . ? C32 C33 H33A 119.5 . . ? C33 C34 C35 118.8(3) . . ? C33 C34 H34A 120.6 . . ? C35 C34 H34A 120.6 . . ? C36 C35 C34 121.7(3) . . ? C36 C35 Cl35 119.2(2) . . ? C34 C35 Cl35 119.1(2) . . ? C37 C36 C35 118.9(3) . . ? C37 C36 H36A 120.6 . . ? C35 C36 H36A 120.6 . . ? C36 C37 C32 120.9(3) . . ? C36 C37 H37A 119.6 . . ? C32 C37 H37A 119.6 . . ? N31 C38 N33 109.3(3) . . ? N31 C38 H38A 125.3 . . ? N33 C38 H38A 125.3 . . ? N32 C39 N33 111.2(3) . . ? N32 C39 H39A 124.4 . . ? N33 C39 H39A 124.4 . . ? C46 C41 C42 118.4(3) . . ? C46 C41 C47 121.2(3) . . ? C42 C41 C47 120.4(3) . . ? C43 C42 C41 119.0(3) . . ? C43 C42 C48 120.5(3) . . ? C41 C42 C48 120.5(3) . . ? C42 C43 C44 121.5(3) . . ? C42 C43 H43A 119.3 . . ? C44 C43 H43A 119.3 . . ? C45 C44 C43 118.8(3) . . ? C45 C44 H44A 120.6 . . ? C43 C44 H44A 120.6 . . ? C44 C45 C46 120.6(3) . . ? C44 C45 H45A 119.7 . . ? C46 C45 H45A 119.7 . . ? C45 C46 C41 121.7(3) . . ? C45 C46 H46A 119.1 . . ? C41 C46 H46A 119.1 . . ? C41 C47 H47A 109.5 . . ? C41 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C41 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C42 C48 H48A 109.5 . . ? C42 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C42 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C56 C51 C52 118.1(3) . . ? C56 C51 C57 121.2(3) . . ? C52 C51 C57 120.7(3) . . ? C53 C52 C51 119.2(3) . . ? C53 C52 C58 119.3(3) . . ? C51 C52 C58 121.5(3) . . ? C52 C53 C54 121.1(3) . . ? C52 C53 H53A 119.5 . . ? C54 C53 H53A 119.5 . . ? C55 C54 C53 119.3(3) . . ? C55 C54 H54A 120.4 . . ? C53 C54 H54A 120.4 . . ? C54 C55 C56 119.3(4) . . ? C54 C55 H55A 120.4 . . ? C56 C55 H55A 120.4 . . ? C51 C56 C55 123.1(4) . . ? C51 C56 H56A 118.5 . . ? C55 C56 H56A 118.5 . . ? C51 C57 H57A 109.5 . . ? C51 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? C51 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? C52 C58 H58A 109.5 . . ? C52 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C52 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 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 C8 N1 N2 C9 0.2(3) . . . . ? Cu1 N1 N2 C9 -177.3(2) . . . . ? C8 N1 N2 Cu2 172.27(19) . . . . ? Cu1 N1 N2 Cu2 -5.2(3) . . . . ? C9 N3 N4 C1 -176.7(3) . . . . ? C8 N3 N4 C1 2.2(5) . . . . ? N3 N4 C1 C2 179.2(3) . . . . ? N4 C1 C2 C7 178.1(3) . . . . ? N4 C1 C2 C3 -1.3(5) . . . . ? C7 C2 C3 C4 1.3(5) . . . . ? C1 C2 C3 C4 -179.3(3) . . . . ? C2 C3 C4 C5 -0.7(5) . . . . ? C3 C4 C5 C6 -0.2(5) . . . . ? C3 C4 C5 Cl5 178.3(2) . . . . ? C4 C5 C6 C7 0.6(5) . . . . ? Cl5 C5 C6 C7 -178.0(2) . . . . ? C3 C2 C7 C6 -0.9(5) . . . . ? C1 C2 C7 C6 179.7(3) . . . . ? C5 C6 C7 C2 -0.1(5) . . . . ? N2 N1 C8 N3 -0.5(3) . . . . ? Cu1 N1 C8 N3 176.6(2) . . . . ? C9 N3 C8 N1 0.7(3) . . . . ? N4 N3 C8 N1 -178.4(3) . . . . ? N1 N2 C9 N3 0.3(3) . . . . ? Cu2 N2 C9 N3 -171.17(19) . . . . ? C8 N3 C9 N2 -0.6(3) . . . . ? N4 N3 C9 N2 178.6(2) . . . . ? C18 N11 N12 C19 0.1(3) . . . . ? Cu2 N11 N12 C19 177.25(19) . . . . ? C18 N11 N12 Cu1 -171.16(19) . . . . ? Cu2 N11 N12 Cu1 6.0(3) . . . . ? C19 N13 N14 C11 174.9(3) . . . . ? C18 N13 N14 C11 -2.2(5) . . . . ? N13 N14 C11 C12 -179.9(2) . . . . ? N14 C11 C12 C17 179.9(3) . . . . ? N14 C11 C12 C13 0.7(5) . . . . ? C17 C12 C13 C14 0.3(5) . . . . ? C11 C12 C13 C14 179.5(3) . . . . ? C12 C13 C14 C15 -1.5(5) . . . . ? C13 C14 C15 C16 2.2(5) . . . . ? C13 C14 C15 Cl15 -177.3(2) . . . . ? C14 C15 C16 C17 -1.6(5) . . . . ? Cl15 C15 C16 C17 177.9(2) . . . . ? C15 C16 C17 C12 0.3(5) . . . . ? C13 C12 C17 C16 0.3(5) . . . . ? C11 C12 C17 C16 -179.0(3) . . . . ? N12 N11 C18 N13 -0.1(3) . . . . ? Cu2 N11 C18 N13 -176.89(19) . . . . ? C19 N13 C18 N11 0.1(3) . . . . ? N14 N13 C18 N11 177.5(3) . . . . ? N11 N12 C19 N13 0.0(3) . . . . ? Cu1 N12 C19 N13 170.61(19) . . . . ? C18 N13 C19 N12 0.0(3) . . . . ? N14 N13 C19 N12 -177.8(2) . . . . ? C28 N21 N22 C29 0.5(3) . . . . ? Cu1 N21 N22 C29 -178.5(2) . . . . ? C28 N23 N24 C21 -7.2(5) . . . . ? C29 N23 N24 C21 174.5(3) . . . . ? N23 N24 C21 C22 179.0(3) . . . . ? N24 C21 C22 C27 -180.0(3) . . . . ? N24 C21 C22 C23 0.6(5) . . . . ? C27 C22 C23 C24 0.6(5) . . . . ? C21 C22 C23 C24 180.0(3) . . . . ? C22 C23 C24 C25 -0.7(5) . . . . ? C23 C24 C25 C26 0.9(5) . . . . ? C23 C24 C25 Cl25 -179.2(2) . . . . ? C24 C25 C26 C27 -0.8(5) . . . . ? Cl25 C25 C26 C27 179.3(2) . . . . ? C25 C26 C27 C22 0.6(5) . . . . ? C23 C22 C27 C26 -0.5(5) . . . . ? C21 C22 C27 C26 -179.9(3) . . . . ? N22 N21 C28 N23 -0.3(3) . . . . ? Cu1 N21 C28 N23 178.6(2) . . . . ? C29 N23 C28 N21 0.0(3) . . . . ? N24 N23 C28 N21 -178.5(3) . . . . ? N21 N22 C29 N23 -0.5(4) . . . . ? C28 N23 C29 N22 0.3(4) . . . . ? N24 N23 C29 N22 179.0(3) . . . . ? C38 N31 N32 C39 -1.2(3) . . . . ? Cu2 N31 N32 C39 172.3(2) . . . . ? C38 N33 N34 C31 -2.0(5) . . . . ? C39 N33 N34 C31 176.7(3) . . . . ? N33 N34 C31 C32 -179.2(2) . . . . ? N34 C31 C32 C33 1.6(4) . . . . ? N34 C31 C32 C37 -179.8(3) . . . . ? C37 C32 C33 C34 0.4(5) . . . . ? C31 C32 C33 C34 179.0(3) . . . . ? C32 C33 C34 C35 0.0(5) . . . . ? C33 C34 C35 C36 -0.3(5) . . . . ? C33 C34 C35 Cl35 -179.3(2) . . . . ? C34 C35 C36 C37 0.2(5) . . . . ? Cl35 C35 C36 C37 179.2(2) . . . . ? C35 C36 C37 C32 0.3(5) . . . . ? C33 C32 C37 C36 -0.6(4) . . . . ? C31 C32 C37 C36 -179.2(3) . . . . ? N32 N31 C38 N33 0.8(3) . . . . ? Cu2 N31 C38 N33 -171.8(2) . . . . ? C39 N33 C38 N31 -0.1(3) . . . . ? N34 N33 C38 N31 178.8(3) . . . . ? N31 N32 C39 N33 1.1(4) . . . . ? C38 N33 C39 N32 -0.6(4) . . . . ? N34 N33 C39 N32 -179.7(3) . . . . ? C46 C41 C42 C43 -0.2(4) . . . . ? C47 C41 C42 C43 -179.0(3) . . . . ? C46 C41 C42 C48 178.9(3) . . . . ? C47 C41 C42 C48 0.2(5) . . . . ? C41 C42 C43 C44 -1.4(5) . . . . ? C48 C42 C43 C44 179.4(3) . . . . ? C42 C43 C44 C45 1.4(5) . . . . ? C43 C44 C45 C46 0.4(5) . . . . ? C44 C45 C46 C41 -2.2(5) . . . . ? C42 C41 C46 C45 2.0(5) . . . . ? C47 C41 C46 C45 -179.2(3) . . . . ? C56 C51 C52 C53 -0.8(5) . . . . ? C57 C51 C52 C53 -179.9(3) . . . . ? C56 C51 C52 C58 177.9(3) . . . . ? C57 C51 C52 C58 -1.2(5) . . . . ? C51 C52 C53 C54 0.7(5) . . . . ? C58 C52 C53 C54 -178.0(3) . . . . ? C52 C53 C54 C55 0.6(5) . . . . ? C53 C54 C55 C56 -1.9(5) . . . . ? C52 C51 C56 C55 -0.6(6) . . . . ? C57 C51 C56 C55 178.5(3) . . . . ? C54 C55 C56 C51 1.9(6) . . . . ? _refine_diff_density_max 0.491 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 949083' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1-m-C8H10 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; bis(\m~2~-4-(E)-(4-chlorobenzylidene)amino-4H-1,2,4-triazole)-bis((E)-4-(chlor obenzylidene)amino-4H-1,2,4-triazole)-di-copper(i) diperchlorate m-xylene disolvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H28 Cl4 Cu2 N16, 2(Cl O4), 2(C8 H10)' _chemical_formula_sum 'C52 H48 Cl6 Cu2 N16 O8' _chemical_formula_weight 1364.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.987(2) _cell_length_b 18.534(3) _cell_length_c 22.097(4) _cell_angle_alpha 90 _cell_angle_beta 94.78(3) _cell_angle_gamma 90 _cell_volume 2851.5(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12938 _cell_measurement_theta_min 2.7706 _cell_measurement_theta_max 36.9286 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.590 _exptl_crystal_F_000 1392 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.09 _exptl_absorpt_coefficient_mu 1.096 _exptl_absorpt_correction_T_min 0.790 _exptl_absorpt_correction_T_max 0.920 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 47177 _diffrn_reflns_av_unetI/netI 0.0960 _diffrn_reflns_av_R_equivalents 0.0690 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.873 _diffrn_reflns_theta_max 33.997 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 11425 _reflns_number_gt 6544 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_structure_solution ; SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.) ; _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0371P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 11425 _refine_ls_number_parameters 380 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0950 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.0814 _refine_ls_wR_factor_gt 0.0736 _refine_ls_goodness_of_fit_ref 0.844 _refine_ls_restrained_S_all 0.844 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.46523(3) 0.43015(2) 0.55175(2) 0.01523(5) Uani 1 1 d . . . . . Cl1 Cl 0.35456(8) 0.46649(2) 0.77781(2) 0.02852(11) Uani 1 1 d . . . . . O1 O 0.3243(4) 0.40272(9) 0.81102(8) 0.0715(6) Uani 1 1 d . . . . . O2 O 0.5142(2) 0.45708(10) 0.74125(7) 0.0502(4) Uani 1 1 d . . . . . O3 O 0.1864(2) 0.48203(10) 0.73713(7) 0.0470(4) Uani 1 1 d . . . . . O4 O 0.3898(2) 0.52577(8) 0.81782(7) 0.0429(4) Uani 1 1 d . . . . . N1 N 0.4071(2) 0.52937(7) 0.57093(6) 0.0147(3) Uani 1 1 d . . . . . N2 N 0.4230(2) 0.58486(7) 0.52880(6) 0.0141(3) Uani 1 1 d . . . . . N3 N 0.3352(2) 0.63087(7) 0.61334(6) 0.0143(3) Uani 1 1 d . . . . . N4 N 0.2863(2) 0.68674(7) 0.65218(6) 0.0160(3) Uani 1 1 d . . . . . C1 C 0.2686(2) 0.66839(9) 0.70721(7) 0.0167(3) Uani 1 1 d . . . . . H1A H 0.2872 0.6195 0.7191 0.020 Uiso 1 1 calc R U . . . C2 C 0.2198(2) 0.72209(9) 0.75215(7) 0.0156(3) Uani 1 1 d . . . . . C3 C 0.1885(2) 0.79498(9) 0.73698(8) 0.0185(3) Uani 1 1 d . . . . . H3A H 0.1995 0.8108 0.6965 0.022 Uiso 1 1 calc R U . . . C4 C 0.1417(3) 0.84391(9) 0.78074(8) 0.0197(4) Uani 1 1 d . . . . . H4A H 0.1184 0.8931 0.7706 0.024 Uiso 1 1 calc R U . . . C5 C 0.1293(2) 0.81972(9) 0.83985(8) 0.0189(3) Uani 1 1 d . . . . . Cl5 Cl 0.07727(7) 0.88134(3) 0.89573(2) 0.02596(10) Uani 1 1 d . . . . . C6 C 0.1586(2) 0.74793(10) 0.85588(8) 0.0193(4) Uani 1 1 d . . . . . H6A H 0.1478 0.7324 0.8964 0.023 Uiso 1 1 calc R U . . . C7 C 0.2040(2) 0.69922(9) 0.81170(8) 0.0181(3) Uani 1 1 d . . . . . H7A H 0.2245 0.6499 0.8220 0.022 Uiso 1 1 calc R U . . . C8 C 0.3535(2) 0.55812(8) 0.62091(7) 0.0161(3) Uani 1 1 d . . . . . H8A H 0.3309 0.5324 0.6568 0.019 Uiso 1 1 calc R U . . . C9 C 0.3792(2) 0.64484(9) 0.55587(7) 0.0152(3) Uani 1 1 d . . . . . H9A H 0.3784 0.6914 0.5378 0.018 Uiso 1 1 calc R U . . . N11 N 0.4199(2) 0.33819(7) 0.58953(6) 0.0158(3) Uani 1 1 d . . . . . N12 N 0.3964(2) 0.27563(8) 0.55457(6) 0.0214(3) Uani 1 1 d . . . . . N13 N 0.3404(2) 0.25148(7) 0.64884(6) 0.0150(3) Uani 1 1 d . . . . . N14 N 0.2951(2) 0.20694(7) 0.69660(6) 0.0167(3) Uani 1 1 d . . . . . C11 C 0.2869(2) 0.23723(9) 0.74825(7) 0.0166(3) Uani 1 1 d . . . . . H11A H 0.3113 0.2874 0.7528 0.020 Uiso 1 1 calc R U . . . C12 C 0.2396(2) 0.19376(9) 0.80035(7) 0.0151(3) Uani 1 1 d . . . . . C13 C 0.2075(3) 0.11926(9) 0.79581(7) 0.0185(3) Uani 1 1 d . . . . . H13A H 0.2167 0.0954 0.7581 0.022 Uiso 1 1 calc R U . . . C14 C 0.1623(3) 0.08042(9) 0.84625(8) 0.0187(3) Uani 1 1 d . . . . . H14A H 0.1413 0.0298 0.8435 0.022 Uiso 1 1 calc R U . . . C15 C 0.1481(2) 0.11622(9) 0.90062(7) 0.0160(3) Uani 1 1 d . . . . . Cl15 Cl 0.09040(6) 0.06720(2) 0.96397(2) 0.02036(9) Uani 1 1 d . . . . . C16 C 0.1796(2) 0.18986(9) 0.90668(7) 0.0184(3) Uani 1 1 d . . . . . H16A H 0.1698 0.2133 0.9445 0.022 Uiso 1 1 calc R U . . . C17 C 0.2257(2) 0.22837(9) 0.85606(7) 0.0175(3) Uani 1 1 d . . . . . H17A H 0.2481 0.2788 0.8593 0.021 Uiso 1 1 calc R U . . . C18 C 0.3865(2) 0.32268(8) 0.64568(7) 0.0151(3) Uani 1 1 d . . . . . H18A H 0.3932 0.3557 0.6787 0.018 Uiso 1 1 calc R U . . . C19 C 0.3488(3) 0.22522(9) 0.59178(8) 0.0216(4) Uani 1 1 d . . . . . H19A H 0.3233 0.1765 0.5804 0.026 Uiso 1 1 calc R U . . . C21 C -0.0159(3) 0.38328(10) -0.00555(9) 0.0282(4) Uani 1 1 d . . . . . C22 C -0.0319(3) 0.41578(10) 0.05065(9) 0.0257(4) Uani 1 1 d . . . . . H22A H -0.1506 0.4124 0.0685 0.031 Uiso 1 1 calc R U . . . C23 C 0.1187(3) 0.45283(10) 0.08156(9) 0.0264(4) Uani 1 1 d . . . . . C24 C 0.2920(3) 0.45786(10) 0.05464(10) 0.0301(4) Uani 1 1 d . . . . . H24A H 0.3977 0.4827 0.0750 0.036 Uiso 1 1 calc R U . . . C25 C 0.3104(3) 0.42680(11) -0.00159(10) 0.0328(5) Uani 1 1 d . . . . . H25A H 0.4286 0.4307 -0.0198 0.039 Uiso 1 1 calc R U . . . C26 C 0.1581(3) 0.39011(10) -0.03153(9) 0.0325(5) Uani 1 1 d . . . . . H26A H 0.1724 0.3694 -0.0702 0.039 Uiso 1 1 calc R U . . . C27 C -0.1833(3) 0.34504(12) -0.03847(11) 0.0417(6) Uani 1 1 d . . . . . H27A H -0.2928 0.3457 -0.0135 0.063 Uiso 1 1 calc R U . . . H27B H -0.1477 0.2950 -0.0463 0.063 Uiso 1 1 calc R U . . . H27C H -0.2187 0.3695 -0.0771 0.063 Uiso 1 1 calc R U . . . C28 C 0.0950(3) 0.48819(12) 0.14178(9) 0.0353(5) Uani 1 1 d . . . . . H28A H -0.0345 0.4787 0.1538 0.053 Uiso 0.27(3) 1 calc R U P A 1 H28B H 0.1141 0.5404 0.1382 0.053 Uiso 0.27(3) 1 calc R U P A 1 H28C H 0.1900 0.4685 0.1725 0.053 Uiso 0.27(3) 1 calc R U P A 1 H28D H 0.2199 0.5057 0.1593 0.053 Uiso 0.73(3) 1 calc R U P A 2 H28E H 0.0438 0.4530 0.1694 0.053 Uiso 0.73(3) 1 calc R U P A 2 H28F H 0.0058 0.5289 0.1359 0.053 Uiso 0.73(3) 1 calc R U P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.02189(11) 0.01171(9) 0.01254(9) 0.00055(8) 0.00404(7) -0.00042(9) Cl1 0.0478(3) 0.0181(2) 0.0191(2) -0.00116(17) -0.0010(2) -0.0003(2) O1 0.140(2) 0.0242(8) 0.0521(11) 0.0182(8) 0.0185(12) 0.0028(10) O2 0.0475(10) 0.0648(11) 0.0388(9) -0.0126(8) 0.0074(8) 0.0133(9) O3 0.0379(9) 0.0746(12) 0.0272(8) 0.0105(8) -0.0049(7) -0.0217(8) O4 0.0440(9) 0.0315(8) 0.0509(10) -0.0231(7) -0.0094(7) 0.0075(7) N1 0.0194(7) 0.0137(6) 0.0113(6) 0.0007(5) 0.0029(5) -0.0014(5) N2 0.0186(7) 0.0117(6) 0.0124(6) 0.0021(5) 0.0031(5) -0.0011(5) N3 0.0177(7) 0.0124(6) 0.0131(6) -0.0017(5) 0.0030(5) -0.0006(5) N4 0.0190(7) 0.0139(7) 0.0156(7) -0.0039(5) 0.0041(5) 0.0001(6) C1 0.0183(8) 0.0155(8) 0.0165(8) -0.0024(6) 0.0019(6) 0.0001(6) C2 0.0149(8) 0.0173(8) 0.0148(8) -0.0049(6) 0.0023(6) -0.0008(6) C3 0.0220(9) 0.0171(8) 0.0166(8) -0.0020(6) 0.0020(7) 0.0006(7) C4 0.0224(9) 0.0156(8) 0.0210(9) -0.0023(7) 0.0011(7) 0.0011(7) C5 0.0167(8) 0.0216(8) 0.0185(8) -0.0102(7) 0.0028(6) 0.0000(7) Cl5 0.0279(2) 0.0276(2) 0.0230(2) -0.01318(18) 0.00510(18) 0.00171(19) C6 0.0187(9) 0.0252(9) 0.0144(8) -0.0028(7) 0.0033(7) -0.0006(7) C7 0.0200(9) 0.0179(8) 0.0168(8) -0.0020(6) 0.0037(7) -0.0003(7) C8 0.0207(9) 0.0145(8) 0.0134(8) 0.0008(6) 0.0028(6) -0.0010(6) C9 0.0188(8) 0.0136(7) 0.0135(8) -0.0002(6) 0.0031(6) -0.0001(6) N11 0.0191(7) 0.0138(6) 0.0148(7) -0.0004(5) 0.0027(5) -0.0004(5) N12 0.0355(9) 0.0147(7) 0.0142(7) -0.0016(6) 0.0040(6) -0.0059(6) N13 0.0193(7) 0.0130(6) 0.0128(7) 0.0020(5) 0.0021(5) -0.0020(5) N14 0.0207(7) 0.0158(7) 0.0138(7) 0.0051(5) 0.0023(5) -0.0026(6) C11 0.0173(8) 0.0158(8) 0.0169(8) 0.0032(6) 0.0018(6) 0.0000(7) C12 0.0155(8) 0.0167(8) 0.0131(7) 0.0025(6) 0.0015(6) 0.0017(6) C13 0.0260(9) 0.0168(8) 0.0129(8) 0.0010(6) 0.0025(7) 0.0002(7) C14 0.0240(9) 0.0157(8) 0.0165(8) 0.0020(6) 0.0018(7) -0.0009(7) C15 0.0141(8) 0.0192(8) 0.0146(8) 0.0069(6) 0.0018(6) 0.0000(6) Cl15 0.0215(2) 0.0253(2) 0.01456(18) 0.00714(16) 0.00344(15) -0.00221(18) C16 0.0212(9) 0.0210(8) 0.0131(8) 0.0010(6) 0.0018(6) 0.0007(7) C17 0.0207(9) 0.0144(8) 0.0174(8) 0.0018(6) 0.0005(7) 0.0005(7) C18 0.0182(8) 0.0122(7) 0.0154(8) 0.0011(6) 0.0037(6) -0.0003(6) C19 0.0346(11) 0.0158(8) 0.0148(8) -0.0002(6) 0.0037(7) -0.0046(7) C21 0.0389(12) 0.0166(9) 0.0292(10) 0.0044(8) 0.0029(8) 0.0060(8) C22 0.0293(10) 0.0216(9) 0.0270(9) 0.0060(8) 0.0068(8) 0.0056(8) C23 0.0326(11) 0.0199(9) 0.0269(10) 0.0082(7) 0.0039(8) 0.0056(8) C24 0.0320(11) 0.0203(9) 0.0385(12) 0.0084(8) 0.0057(9) 0.0022(8) C25 0.0360(12) 0.0233(10) 0.0414(12) 0.0115(9) 0.0168(9) 0.0081(9) C26 0.0499(14) 0.0211(10) 0.0279(10) 0.0031(8) 0.0118(9) 0.0101(9) C27 0.0509(15) 0.0307(11) 0.0430(13) -0.0047(10) 0.0009(11) 0.0000(10) C28 0.0418(13) 0.0367(12) 0.0271(11) 0.0037(9) 0.0012(9) 0.0039(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N11 1.9356(14) . ? Cu N1 1.9379(14) . ? Cu N2 2.0215(14) 3_666 ? Cl1 O1 1.4163(17) . ? Cl1 O4 1.4188(15) . ? Cl1 O2 1.4414(17) . ? Cl1 O3 1.4474(17) . ? N1 C8 1.309(2) . ? N1 N2 1.3979(18) . ? N2 C9 1.311(2) . ? N2 Cu 2.0214(14) 3_666 ? N3 C9 1.356(2) . ? N3 C8 1.363(2) . ? N3 N4 1.4052(18) . ? N4 C1 1.279(2) . ? C1 C2 1.466(2) . ? C1 H1A 0.9500 . ? C2 C7 1.395(2) . ? C2 C3 1.405(2) . ? C3 C4 1.385(2) . ? C3 H3A 0.9500 . ? C4 C5 1.391(2) . ? C4 H4A 0.9500 . ? C5 C6 1.388(2) . ? C5 Cl5 1.7423(16) . ? C6 C7 1.386(2) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? N11 C18 1.313(2) . ? N11 N12 1.3954(19) . ? N12 C19 1.306(2) . ? N13 C19 1.357(2) . ? N13 C18 1.361(2) . ? N13 N14 1.3970(18) . ? N14 C11 1.277(2) . ? C11 C12 1.465(2) . ? C11 H11A 0.9500 . ? C12 C17 1.399(2) . ? C12 C13 1.401(2) . ? C13 C14 1.385(2) . ? C13 H13A 0.9500 . ? C14 C15 1.383(2) . ? C14 H14A 0.9500 . ? C15 C16 1.387(2) . ? C15 Cl15 1.7441(16) . ? C16 C17 1.387(2) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C21 C22 1.393(3) . ? C21 C26 1.393(3) . ? C21 C27 1.503(3) . ? C22 C23 1.388(3) . ? C22 H22A 0.9500 . ? C23 C24 1.396(3) . ? C23 C28 1.505(3) . ? C24 C25 1.385(3) . ? C24 H24A 0.9500 . ? C25 C26 1.384(3) . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C28 H28D 0.9800 . ? C28 H28E 0.9800 . ? C28 H28F 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 N11 Cu N1 134.14(6) . . ? N11 Cu N2 110.34(6) . 3_666 ? N1 Cu N2 115.26(5) . 3_666 ? O1 Cl1 O4 110.43(11) . . ? O1 Cl1 O2 110.20(12) . . ? O4 Cl1 O2 109.94(11) . . ? O1 Cl1 O3 109.85(12) . . ? O4 Cl1 O3 108.81(10) . . ? O2 Cl1 O3 107.56(10) . . ? C8 N1 N2 107.87(13) . . ? C8 N1 Cu 130.61(11) . . ? N2 N1 Cu 121.51(10) . . ? C9 N2 N1 106.58(13) . . ? C9 N2 Cu 129.84(11) . 3_666 ? N1 N2 Cu 122.90(10) . 3_666 ? C9 N3 C8 106.12(13) . . ? C9 N3 N4 121.11(13) . . ? C8 N3 N4 132.76(13) . . ? C1 N4 N3 115.63(14) . . ? N4 C1 C2 120.66(15) . . ? N4 C1 H1A 119.7 . . ? C2 C1 H1A 119.7 . . ? C7 C2 C3 119.62(15) . . ? C7 C2 C1 118.26(15) . . ? C3 C2 C1 122.13(15) . . ? C4 C3 C2 120.30(16) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C3 C4 C5 118.80(16) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? C6 C5 C4 121.96(15) . . ? C6 C5 Cl5 118.87(13) . . ? C4 C5 Cl5 119.17(13) . . ? C7 C6 C5 118.85(16) . . ? C7 C6 H6A 120.6 . . ? C5 C6 H6A 120.6 . . ? C6 C7 C2 120.47(16) . . ? C6 C7 H7A 119.8 . . ? C2 C7 H7A 119.8 . . ? N1 C8 N3 109.24(14) . . ? N1 C8 H8A 125.4 . . ? N3 C8 H8A 125.4 . . ? N2 C9 N3 110.19(14) . . ? N2 C9 H9A 124.9 . . ? N3 C9 H9A 124.9 . . ? C18 N11 N12 108.61(13) . . ? C18 N11 Cu 130.44(11) . . ? N12 N11 Cu 120.58(10) . . ? C19 N12 N11 105.68(13) . . ? C19 N13 C18 105.75(13) . . ? C19 N13 N14 121.32(13) . . ? C18 N13 N14 132.92(13) . . ? C11 N14 N13 116.43(14) . . ? N14 C11 C12 119.35(15) . . ? N14 C11 H11A 120.3 . . ? C12 C11 H11A 120.3 . . ? C17 C12 C13 119.51(15) . . ? C17 C12 C11 118.43(15) . . ? C13 C12 C11 122.06(15) . . ? C14 C13 C12 120.02(15) . . ? C14 C13 H13A 120.0 . . ? C12 C13 H13A 120.0 . . ? C15 C14 C13 119.16(15) . . ? C15 C14 H14A 120.4 . . ? C13 C14 H14A 120.4 . . ? C14 C15 C16 122.24(15) . . ? C14 C15 Cl15 119.04(13) . . ? C16 C15 Cl15 118.72(13) . . ? C15 C16 C17 118.30(15) . . ? C15 C16 H16A 120.9 . . ? C17 C16 H16A 120.9 . . ? C16 C17 C12 120.77(16) . . ? C16 C17 H17A 119.6 . . ? C12 C17 H17A 119.6 . . ? N11 C18 N13 108.79(14) . . ? N11 C18 H18A 125.6 . . ? N13 C18 H18A 125.6 . . ? N12 C19 N13 111.18(15) . . ? N12 C19 H19A 124.4 . . ? N13 C19 H19A 124.4 . . ? C22 C21 C26 117.7(2) . . ? C22 C21 C27 121.24(19) . . ? C26 C21 C27 120.96(19) . . ? C23 C22 C21 122.61(19) . . ? C23 C22 H22A 118.7 . . ? C21 C22 H22A 118.7 . . ? C22 C23 C24 118.20(19) . . ? C22 C23 C28 121.06(18) . . ? C24 C23 C28 120.72(19) . . ? C25 C24 C23 120.2(2) . . ? C25 C24 H24A 119.9 . . ? C23 C24 H24A 119.9 . . ? C26 C25 C24 120.51(19) . . ? C26 C25 H25A 119.7 . . ? C24 C25 H25A 119.7 . . ? C25 C26 C21 120.71(19) . . ? C25 C26 H26A 119.6 . . ? C21 C26 H26A 119.6 . . ? C21 C27 H27A 109.5 . . ? C21 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C21 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C23 C28 H28A 109.5 . . ? C23 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C23 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C23 C28 H28D 109.5 . . ? C23 C28 H28E 109.5 . . ? H28D C28 H28E 109.5 . . ? C23 C28 H28F 109.5 . . ? H28D C28 H28F 109.5 . . ? H28E C28 H28F 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 C8 N1 N2 C9 0.44(18) . . . . ? Cu N1 N2 C9 -178.36(11) . . . . ? C8 N1 N2 Cu 171.86(11) . . . 3_666 ? Cu N1 N2 Cu -6.95(17) . . . 3_666 ? C9 N3 N4 C1 -172.49(15) . . . . ? C8 N3 N4 C1 6.2(3) . . . . ? N3 N4 C1 C2 179.42(14) . . . . ? N4 C1 C2 C7 -179.40(16) . . . . ? N4 C1 C2 C3 0.7(3) . . . . ? C7 C2 C3 C4 -0.2(3) . . . . ? C1 C2 C3 C4 179.66(16) . . . . ? C2 C3 C4 C5 1.0(3) . . . . ? C3 C4 C5 C6 -1.3(3) . . . . ? C3 C4 C5 Cl5 178.16(13) . . . . ? C4 C5 C6 C7 0.8(3) . . . . ? Cl5 C5 C6 C7 -178.63(13) . . . . ? C5 C6 C7 C2 0.0(3) . . . . ? C3 C2 C7 C6 -0.3(2) . . . . ? C1 C2 C7 C6 179.86(16) . . . . ? N2 N1 C8 N3 -0.54(18) . . . . ? Cu N1 C8 N3 178.12(11) . . . . ? C9 N3 C8 N1 0.43(18) . . . . ? N4 N3 C8 N1 -178.44(15) . . . . ? N1 N2 C9 N3 -0.18(18) . . . . ? Cu N2 C9 N3 -170.78(11) 3_666 . . . ? C8 N3 C9 N2 -0.14(18) . . . . ? N4 N3 C9 N2 178.89(14) . . . . ? C18 N11 N12 C19 0.25(19) . . . . ? Cu N11 N12 C19 -173.50(12) . . . . ? C19 N13 N14 C11 -178.54(16) . . . . ? C18 N13 N14 C11 2.8(3) . . . . ? N13 N14 C11 C12 179.87(14) . . . . ? N14 C11 C12 C17 -178.09(16) . . . . ? N14 C11 C12 C13 1.6(2) . . . . ? C17 C12 C13 C14 0.0(3) . . . . ? C11 C12 C13 C14 -179.71(16) . . . . ? C12 C13 C14 C15 0.5(3) . . . . ? C13 C14 C15 C16 -0.7(3) . . . . ? C13 C14 C15 Cl15 179.78(13) . . . . ? C14 C15 C16 C17 0.3(3) . . . . ? Cl15 C15 C16 C17 179.91(13) . . . . ? C15 C16 C17 C12 0.1(3) . . . . ? C13 C12 C17 C16 -0.3(3) . . . . ? C11 C12 C17 C16 179.41(16) . . . . ? N12 N11 C18 N13 -0.28(18) . . . . ? Cu N11 C18 N13 172.64(11) . . . . ? C19 N13 C18 N11 0.21(19) . . . . ? N14 N13 C18 N11 178.97(15) . . . . ? N11 N12 C19 N13 -0.1(2) . . . . ? C18 N13 C19 N12 0.0(2) . . . . ? N14 N13 C19 N12 -178.99(15) . . . . ? C26 C21 C22 C23 -1.3(3) . . . . ? C27 C21 C22 C23 -178.55(18) . . . . ? C21 C22 C23 C24 0.5(3) . . . . ? C21 C22 C23 C28 179.08(17) . . . . ? C22 C23 C24 C25 0.4(3) . . . . ? C28 C23 C24 C25 -178.21(18) . . . . ? C23 C24 C25 C26 -0.4(3) . . . . ? C24 C25 C26 C21 -0.5(3) . . . . ? C22 C21 C26 C25 1.3(3) . . . . ? C27 C21 C26 C25 178.53(19) . . . . ? _refine_diff_density_max 0.651 _refine_diff_density_min -0.494 _refine_diff_density_rms 0.084 _database_code_depnum_ccdc_archive 'CCDC 949084' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1-p-C8H10 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; bis(\m~2~-4-(E)-(4-chlorobenzylidene)amino-4H-1,2,4-triazole)-bis((E)-4-(chlor obenzylidene)amino-4H-1,2,4-triazole)-di-copper(i) diperchlorate p-xylene disolvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H28 Cl4 Cu2 N16, 2(Cl O4), 2(C8 H10)' _chemical_formula_sum 'C52 H48 Cl6 Cu2 N16 O8' _chemical_formula_weight 1364.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.946(2) _cell_length_b 18.278(3) _cell_length_c 22.450(4) _cell_angle_alpha 90 _cell_angle_beta 91.75(3) _cell_angle_gamma 90 _cell_volume 2848.9(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6479 _cell_measurement_theta_min 2.8672 _cell_measurement_theta_max 28.7776 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.591 _exptl_crystal_F_000 1392 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_absorpt_coefficient_mu 1.097 _exptl_absorpt_correction_T_min 0.849 _exptl_absorpt_correction_T_max 0.940 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24142 _diffrn_reflns_av_unetI/netI 0.1033 _diffrn_reflns_av_R_equivalents 0.0836 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.875 _diffrn_reflns_theta_max 26.998 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 6207 _reflns_number_gt 3370 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_structure_solution ; SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.) ; _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0315P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 6207 _refine_ls_number_parameters 408 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1048 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0768 _refine_ls_wR_factor_gt 0.0652 _refine_ls_goodness_of_fit_ref 0.847 _refine_ls_restrained_S_all 0.849 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.46468(5) 0.92811(2) 0.04981(2) 0.02658(11) Uani 1 1 d . . . . . Cl1 Cl 0.32456(13) 0.95646(5) 0.27809(4) 0.0422(2) Uani 1 1 d . . . . . O1 O 0.3986(4) 1.02139(12) 0.30429(11) 0.0604(7) Uani 1 1 d . . . . . O2 O 0.2004(8) 0.9654(4) 0.2263(2) 0.0553(16) Uani 0.723(10) 1 d . U P A 1 O3 O 0.2115(8) 0.9165(3) 0.32308(19) 0.0449(13) Uani 0.723(10) 1 d . U P A 1 O4 O 0.4788(6) 0.9092(3) 0.2624(3) 0.0649(19) Uani 0.723(10) 1 d . . P A 1 O21 O 0.1629(18) 0.9947(7) 0.2486(6) 0.040(3) Uani 0.277(10) 1 d . U P A 2 O31 O 0.297(2) 0.8992(7) 0.3074(7) 0.055(3) Uani 0.277(10) 1 d . U P A 2 O41 O 0.4698(16) 0.9472(7) 0.2285(6) 0.062(4) Uani 0.277(10) 1 d . U P A 2 N1 N 0.3944(3) 1.02683(12) 0.06986(10) 0.0237(6) Uani 1 1 d . . . . . N2 N 0.4088(3) 1.08455(12) 0.02912(10) 0.0238(6) Uani 1 1 d . . . . . N3 N 0.3108(3) 1.12846(12) 0.11375(10) 0.0231(6) Uani 1 1 d . . . . . N4 N 0.2591(3) 1.18350(12) 0.15379(10) 0.0252(6) Uani 1 1 d . . . . . C1 C 0.2355(4) 1.16256(16) 0.20745(13) 0.0263(7) Uani 1 1 d . . . . . H1 H 0.2489 1.1122 0.2172 0.032 Uiso 1 1 calc R U . . . C2 C 0.1883(4) 1.21500(16) 0.25395(13) 0.0244(7) Uani 1 1 d . . . . . C3 C 0.1666(4) 1.28959(16) 0.24184(13) 0.0291(7) Uani 1 1 d . . . . . H3 H 0.1785 1.3071 0.2023 0.035 Uiso 1 1 calc R U . . . C4 C 0.1280(4) 1.33798(17) 0.28712(14) 0.0324(8) Uani 1 1 d . . . . . H4 H 0.1146 1.3888 0.2791 0.039 Uiso 1 1 calc R U . . . C5 C 0.1093(4) 1.31125(18) 0.34438(13) 0.0312(8) Uani 1 1 d . . . . . Cl5 Cl 0.06670(12) 1.37240(5) 0.40197(4) 0.0411(2) Uani 1 1 d . . . . . C6 C 0.1251(4) 1.23765(17) 0.35747(14) 0.0313(8) Uani 1 1 d . . . . . H6 H 0.1094 1.2201 0.3969 0.038 Uiso 1 1 calc R U . . . C7 C 0.1647(4) 1.19015(17) 0.31136(13) 0.0283(7) Uani 1 1 d . . . . . H7 H 0.1758 1.1393 0.3194 0.034 Uiso 1 1 calc R U . . . C8 C 0.3348(4) 1.05493(15) 0.11995(13) 0.0249(7) Uani 1 1 d . . . . . H8 H 0.3118 1.0279 0.1552 0.030 Uiso 1 1 calc R U . . . C9 C 0.3579(4) 1.14410(16) 0.05722(13) 0.0252(7) Uani 1 1 d . . . . . H9 H 0.3547 1.1917 0.0402 0.030 Uiso 1 1 calc R U . . . N11 N 0.4357(3) 0.83396(13) 0.08708(10) 0.0258(6) Uani 1 1 d . . . . . N12 N 0.4602(4) 0.76819(13) 0.05610(11) 0.0330(6) Uani 1 1 d . . . . . N13 N 0.3817(3) 0.74455(13) 0.14842(10) 0.0258(6) Uani 1 1 d . . . . . N14 N 0.3356(3) 0.69985(13) 0.19622(11) 0.0273(6) Uani 1 1 d . . . . . C11 C 0.3146(4) 0.73140(16) 0.24606(13) 0.0273(7) Uani 1 1 d . . . . . H11 H 0.3321 0.7828 0.2495 0.033 Uiso 1 1 calc R U . . . C12 C 0.2636(4) 0.68825(16) 0.29819(13) 0.0248(7) Uani 1 1 d . . . . . C13 C 0.2395(4) 0.61279(16) 0.29524(13) 0.0277(7) Uani 1 1 d . . . . . H13 H 0.2567 0.5879 0.2587 0.033 Uiso 1 1 calc R U . . . C14 C 0.1907(4) 0.57409(17) 0.34518(13) 0.0272(7) Uani 1 1 d . . . . . H14 H 0.1730 0.5226 0.3432 0.033 Uiso 1 1 calc R U . . . C15 C 0.1677(4) 0.61115(17) 0.39832(13) 0.0266(7) Uani 1 1 d . . . . . Cl15 Cl 0.10630(10) 0.56228(4) 0.46149(3) 0.03061(19) Uani 1 1 d . . . . . C16 C 0.1909(4) 0.68591(16) 0.40263(13) 0.0269(7) Uani 1 1 d . . . . . H16 H 0.1740 0.7106 0.4393 0.032 Uiso 1 1 calc R U . . . C17 C 0.2395(4) 0.72399(16) 0.35200(13) 0.0275(7) Uani 1 1 d . . . . . H17 H 0.2568 0.7755 0.3541 0.033 Uiso 1 1 calc R U . . . C18 C 0.3911(4) 0.81828(16) 0.14155(13) 0.0273(7) Uani 1 1 d . . . . . H18 H 0.3685 0.8532 0.1719 0.033 Uiso 1 1 calc R U . . . C19 C 0.4270(4) 0.71691(17) 0.09478(13) 0.0335(8) Uani 1 1 d . . . . . H19 H 0.4339 0.6661 0.0863 0.040 Uiso 1 1 calc R U . . . C21 C 0.0064(5) 1.07066(17) 0.44143(14) 0.0362(8) Uani 1 1 d . . . . . C22 C -0.0472(5) 1.11442(19) 0.48832(16) 0.0460(9) Uani 1 1 d . . . . . H22 H -0.1785 1.1281 0.4911 0.055 Uiso 1 1 calc R U . . . C23 C 0.0841(5) 1.13880(18) 0.53120(16) 0.0453(9) Uani 1 1 d . . . . . H23 H 0.0413 1.1685 0.5629 0.054 Uiso 1 1 calc R U . . . C24 C 0.2758(5) 1.12081(18) 0.52889(15) 0.0421(9) Uani 1 1 d . . . . . C25 C 0.3315(5) 1.07680(17) 0.48199(15) 0.0385(8) Uani 1 1 d . . . . . H25 H 0.4629 1.0631 0.4793 0.046 Uiso 1 1 calc R U . . . C26 C 0.2001(5) 1.05260(16) 0.43925(15) 0.0395(9) Uani 1 1 d . . . . . H26 H 0.2430 1.0229 0.4076 0.047 Uiso 1 1 calc R U . . . C27 C -0.1351(5) 1.04387(18) 0.39411(15) 0.0481(10) Uani 1 1 d . . . . . H27A H -0.1726 1.0846 0.3678 0.072 Uiso 1 1 calc R U . . . H27B H -0.2496 1.0243 0.4130 0.072 Uiso 1 1 calc R U . . . H27C H -0.0752 1.0053 0.3707 0.072 Uiso 1 1 calc R U . . . C28 C 0.4214(5) 1.1453(2) 0.57589(16) 0.0599(11) Uani 1 1 d . . . . . H28A H 0.3575 1.1755 0.6054 0.090 Uiso 1 1 calc R U . . . H28B H 0.5225 1.1739 0.5572 0.090 Uiso 1 1 calc R U . . . H28C H 0.4788 1.1023 0.5956 0.090 Uiso 1 1 calc R U . . . 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 0.0314(2) 0.0234(2) 0.0251(2) 0.00031(18) 0.00438(16) 0.00001(19) Cl1 0.0560(6) 0.0387(5) 0.0316(5) -0.0039(4) -0.0024(4) 0.0054(5) O1 0.077(2) 0.0376(15) 0.0673(18) -0.0179(13) 0.0162(15) -0.0159(14) O2 0.059(3) 0.074(4) 0.033(3) 0.023(2) -0.010(2) -0.024(3) O3 0.066(3) 0.039(3) 0.030(2) 0.0096(18) 0.013(2) -0.001(2) O4 0.060(3) 0.056(3) 0.080(4) -0.030(3) 0.015(3) 0.016(2) O21 0.039(5) 0.041(6) 0.041(6) 0.010(4) -0.002(5) 0.003(4) O31 0.080(7) 0.036(5) 0.049(6) 0.025(5) -0.004(5) -0.009(5) O41 0.072(6) 0.052(7) 0.062(7) -0.006(5) 0.003(5) 0.012(5) N1 0.0258(15) 0.0235(14) 0.0222(14) 0.0024(11) 0.0062(11) 0.0018(11) N2 0.0254(14) 0.0196(14) 0.0264(14) 0.0025(11) 0.0010(11) -0.0012(11) N3 0.0263(14) 0.0229(15) 0.0203(14) -0.0021(11) 0.0022(11) -0.0007(11) N4 0.0283(15) 0.0247(14) 0.0228(15) -0.0072(11) 0.0048(11) -0.0002(11) C1 0.0250(18) 0.0257(18) 0.0281(19) -0.0020(14) 0.0012(14) -0.0006(14) C2 0.0180(17) 0.0289(18) 0.0263(18) -0.0031(14) 0.0009(13) 0.0006(14) C3 0.0327(19) 0.0297(19) 0.0253(18) -0.0022(14) 0.0050(15) 0.0006(15) C4 0.035(2) 0.0256(18) 0.036(2) -0.0086(15) 0.0011(16) -0.0008(15) C5 0.0266(19) 0.036(2) 0.031(2) -0.0128(15) 0.0016(15) -0.0023(15) Cl5 0.0386(5) 0.0445(5) 0.0405(5) -0.0202(4) 0.0044(4) 0.0013(4) C6 0.0296(19) 0.039(2) 0.0253(18) -0.0027(15) 0.0036(15) -0.0030(15) C7 0.0256(18) 0.0306(18) 0.0290(19) -0.0020(15) 0.0043(14) 0.0032(14) C8 0.0264(17) 0.0252(19) 0.0235(17) 0.0010(13) 0.0040(14) -0.0024(14) C9 0.0241(17) 0.0256(18) 0.0258(18) -0.0016(14) 0.0022(14) -0.0009(14) N11 0.0296(15) 0.0256(15) 0.0225(15) -0.0003(11) 0.0059(12) 0.0033(11) N12 0.0456(17) 0.0260(15) 0.0276(15) -0.0013(13) 0.0058(13) -0.0015(14) N13 0.0270(15) 0.0266(15) 0.0239(15) 0.0034(12) 0.0044(12) -0.0027(12) N14 0.0310(16) 0.0264(15) 0.0248(15) 0.0067(12) 0.0036(12) -0.0018(12) C11 0.0244(18) 0.0284(18) 0.0292(19) 0.0032(15) -0.0002(14) -0.0001(14) C12 0.0230(17) 0.0268(18) 0.0245(18) 0.0041(14) 0.0001(13) 0.0006(14) C13 0.0307(19) 0.0263(18) 0.0263(18) 0.0008(14) 0.0020(14) 0.0019(14) C14 0.0301(18) 0.0195(16) 0.0318(18) 0.0013(15) -0.0003(14) -0.0001(15) C15 0.0214(17) 0.0307(19) 0.0278(18) 0.0073(14) 0.0019(14) 0.0002(14) Cl15 0.0320(4) 0.0324(5) 0.0276(4) 0.0076(3) 0.0035(3) -0.0015(4) C16 0.0268(18) 0.0286(18) 0.0252(18) 0.0000(14) 0.0016(14) 0.0005(14) C17 0.0235(18) 0.0271(18) 0.0319(19) 0.0034(15) -0.0018(14) 0.0010(14) C18 0.0308(19) 0.0258(18) 0.0256(18) 0.0012(14) 0.0037(14) 0.0026(14) C19 0.050(2) 0.0219(18) 0.0288(19) -0.0012(15) 0.0066(16) -0.0048(16) C21 0.044(2) 0.0302(18) 0.035(2) 0.0078(16) 0.0059(16) 0.0054(18) C22 0.047(2) 0.048(2) 0.043(2) 0.0051(18) 0.0100(19) 0.0186(19) C23 0.057(3) 0.038(2) 0.041(2) -0.0031(17) 0.003(2) 0.0180(19) C24 0.053(2) 0.031(2) 0.042(2) 0.0037(17) 0.0036(19) 0.0054(18) C25 0.039(2) 0.035(2) 0.043(2) 0.0069(17) 0.0100(17) 0.0046(17) C26 0.050(2) 0.031(2) 0.038(2) 0.0035(16) 0.0131(18) 0.0024(17) C27 0.055(2) 0.043(2) 0.047(2) 0.0053(18) 0.0024(19) 0.0056(18) C28 0.068(3) 0.048(2) 0.062(3) -0.005(2) -0.011(2) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N1 1.926(2) . ? Cu N11 1.927(2) . ? Cu N2 2.015(2) 3_675 ? Cl1 O31 1.254(12) . ? Cl1 O1 1.414(2) . ? Cl1 O4 1.428(4) . ? Cl1 O2 1.436(5) . ? Cl1 O21 1.464(12) . ? Cl1 O3 1.489(5) . ? Cl1 O41 1.535(12) . ? N1 C8 1.315(3) . ? N1 N2 1.402(3) . ? N2 C9 1.312(3) . ? N2 Cu 2.015(2) 3_675 ? N3 C9 1.351(3) . ? N3 C8 1.361(3) . ? N3 N4 1.403(3) . ? N4 C1 1.279(3) . ? C1 C2 1.462(4) . ? C1 H1 0.9500 . ? C2 C7 1.381(4) . ? C2 C3 1.397(4) . ? C3 C4 1.380(4) . ? C3 H3 0.9500 . ? C4 C5 1.385(4) . ? C4 H4 0.9500 . ? C5 C6 1.381(4) . ? C5 Cl5 1.741(3) . ? C6 C7 1.385(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? N11 C18 1.303(3) . ? N11 N12 1.402(3) . ? N12 C19 1.303(3) . ? N13 C19 1.352(3) . ? N13 C18 1.358(3) . ? N13 N14 1.394(3) . ? N14 C11 1.271(3) . ? C11 C12 1.464(4) . ? C11 H11 0.9500 . ? C12 C17 1.388(4) . ? C12 C13 1.391(4) . ? C13 C14 1.377(4) . ? C13 H13 0.9500 . ? C14 C15 1.385(4) . ? C14 H14 0.9500 . ? C15 C16 1.379(4) . ? C15 Cl15 1.740(3) . ? C16 C17 1.384(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C21 C22 1.382(4) . ? C21 C26 1.387(4) . ? C21 C27 1.507(4) . ? C22 C23 1.380(4) . ? C22 H22 0.9500 . ? C23 C24 1.374(4) . ? C23 H23 0.9500 . ? C24 C25 1.389(4) . ? C24 C28 1.507(5) . ? C25 C26 1.377(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 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 N1 Cu N11 134.80(10) . . ? N1 Cu N2 115.69(9) . 3_675 ? N11 Cu N2 109.48(9) . 3_675 ? O31 Cl1 O1 122.8(7) . . ? O1 Cl1 O4 110.1(2) . . ? O1 Cl1 O2 116.3(3) . . ? O4 Cl1 O2 107.8(3) . . ? O31 Cl1 O21 120.5(9) . . ? O1 Cl1 O21 92.9(6) . . ? O1 Cl1 O3 108.8(2) . . ? O4 Cl1 O3 106.6(3) . . ? O2 Cl1 O3 106.8(3) . . ? O31 Cl1 O41 113.8(7) . . ? O1 Cl1 O41 99.0(4) . . ? O21 Cl1 O41 103.7(6) . . ? C8 N1 N2 107.1(2) . . ? C8 N1 Cu 130.9(2) . . ? N2 N1 Cu 121.93(18) . . ? C9 N2 N1 106.6(2) . . ? C9 N2 Cu 130.5(2) . 3_675 ? N1 N2 Cu 121.93(17) . 3_675 ? C9 N3 C8 105.8(2) . . ? C9 N3 N4 121.6(2) . . ? C8 N3 N4 132.5(2) . . ? C1 N4 N3 115.6(2) . . ? N4 C1 C2 120.9(3) . . ? N4 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C7 C2 C3 119.2(3) . . ? C7 C2 C1 119.1(3) . . ? C3 C2 C1 121.7(3) . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 118.9(3) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 122.2(3) . . ? C6 C5 Cl5 118.8(2) . . ? C4 C5 Cl5 119.1(3) . . ? C5 C6 C7 117.9(3) . . ? C5 C6 H6 121.1 . . ? C7 C6 H6 121.1 . . ? C2 C7 C6 121.6(3) . . ? C2 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? N1 C8 N3 109.8(2) . . ? N1 C8 H8 125.1 . . ? N3 C8 H8 125.1 . . ? N2 C9 N3 110.6(3) . . ? N2 C9 H9 124.7 . . ? N3 C9 H9 124.7 . . ? C18 N11 N12 108.3(2) . . ? C18 N11 Cu 129.4(2) . . ? N12 N11 Cu 122.31(17) . . ? C19 N12 N11 105.0(2) . . ? C19 N13 C18 104.9(2) . . ? C19 N13 N14 122.1(2) . . ? C18 N13 N14 133.0(2) . . ? C11 N14 N13 116.5(2) . . ? N14 C11 C12 119.8(3) . . ? N14 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C17 C12 C13 119.4(3) . . ? C17 C12 C11 118.7(3) . . ? C13 C12 C11 121.9(3) . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 119.2(3) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C16 C15 C14 121.9(3) . . ? C16 C15 Cl15 118.8(2) . . ? C14 C15 Cl15 119.2(2) . . ? C15 C16 C17 118.2(3) . . ? C15 C16 H16 120.9 . . ? C17 C16 H16 120.9 . . ? C16 C17 C12 121.1(3) . . ? C16 C17 H17 119.4 . . ? C12 C17 H17 119.4 . . ? N11 C18 N13 109.8(3) . . ? N11 C18 H18 125.1 . . ? N13 C18 H18 125.1 . . ? N12 C19 N13 112.1(3) . . ? N12 C19 H19 124.0 . . ? N13 C19 H19 124.0 . . ? C22 C21 C26 116.7(3) . . ? C22 C21 C27 122.7(3) . . ? C26 C21 C27 120.7(3) . . ? C23 C22 C21 122.0(3) . . ? C23 C22 H22 119.0 . . ? C21 C22 H22 119.0 . . ? C24 C23 C22 121.1(3) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C23 C24 C25 117.4(3) . . ? C23 C24 C28 122.2(3) . . ? C25 C24 C28 120.4(3) . . ? C26 C25 C24 121.4(3) . . ? C26 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? C25 C26 C21 121.4(3) . . ? C25 C26 H26 119.3 . . ? C21 C26 H26 119.3 . . ? C21 C27 H27A 109.5 . . ? C21 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C21 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 C8 N1 N2 C9 0.3(3) . . . . ? Cu N1 N2 C9 -177.54(18) . . . . ? C8 N1 N2 Cu 169.91(18) . . . 3_675 ? Cu N1 N2 Cu -8.0(3) . . . 3_675 ? C9 N3 N4 C1 -173.6(3) . . . . ? C8 N3 N4 C1 2.9(4) . . . . ? N3 N4 C1 C2 177.8(2) . . . . ? N4 C1 C2 C7 -179.8(3) . . . . ? N4 C1 C2 C3 0.2(4) . . . . ? C7 C2 C3 C4 2.0(4) . . . . ? C1 C2 C3 C4 -177.9(3) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C3 C4 C5 C6 -1.0(5) . . . . ? C3 C4 C5 Cl5 178.4(2) . . . . ? C4 C5 C6 C7 1.2(4) . . . . ? Cl5 C5 C6 C7 -178.1(2) . . . . ? C3 C2 C7 C6 -1.8(4) . . . . ? C1 C2 C7 C6 178.2(3) . . . . ? C5 C6 C7 C2 0.2(4) . . . . ? N2 N1 C8 N3 -0.4(3) . . . . ? Cu N1 C8 N3 177.24(18) . . . . ? C9 N3 C8 N1 0.3(3) . . . . ? N4 N3 C8 N1 -176.6(3) . . . . ? N1 N2 C9 N3 -0.2(3) . . . . ? Cu N2 C9 N3 -168.53(18) 3_675 . . . ? C8 N3 C9 N2 0.0(3) . . . . ? N4 N3 C9 N2 177.3(2) . . . . ? C18 N11 N12 C19 0.3(3) . . . . ? Cu N11 N12 C19 -179.1(2) . . . . ? C19 N13 N14 C11 173.1(3) . . . . ? C18 N13 N14 C11 -8.0(4) . . . . ? N13 N14 C11 C12 179.2(2) . . . . ? N14 C11 C12 C17 -179.4(3) . . . . ? N14 C11 C12 C13 0.9(4) . . . . ? C17 C12 C13 C14 0.5(4) . . . . ? C11 C12 C13 C14 -179.7(3) . . . . ? C12 C13 C14 C15 -0.6(4) . . . . ? C13 C14 C15 C16 0.5(4) . . . . ? C13 C14 C15 Cl15 -179.9(2) . . . . ? C14 C15 C16 C17 -0.3(4) . . . . ? Cl15 C15 C16 C17 -180.0(2) . . . . ? C15 C16 C17 C12 0.3(4) . . . . ? C13 C12 C17 C16 -0.4(4) . . . . ? C11 C12 C17 C16 179.9(3) . . . . ? N12 N11 C18 N13 -0.9(3) . . . . ? Cu N11 C18 N13 178.49(18) . . . . ? C19 N13 C18 N11 1.1(3) . . . . ? N14 N13 C18 N11 -178.0(3) . . . . ? N11 N12 C19 N13 0.4(3) . . . . ? C18 N13 C19 N12 -0.9(3) . . . . ? N14 N13 C19 N12 178.3(2) . . . . ? C26 C21 C22 C23 -0.4(5) . . . . ? C27 C21 C22 C23 -179.7(3) . . . . ? C21 C22 C23 C24 0.4(5) . . . . ? C22 C23 C24 C25 -0.4(5) . . . . ? C22 C23 C24 C28 -178.6(3) . . . . ? C23 C24 C25 C26 0.5(5) . . . . ? C28 C24 C25 C26 178.6(3) . . . . ? C24 C25 C26 C21 -0.5(5) . . . . ? C22 C21 C26 C25 0.4(5) . . . . ? C27 C21 C26 C25 179.8(3) . . . . ? _refine_diff_density_max 0.425 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 949085' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1-C10H8 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; bis(\m~2~-4-(E)-(4-chlorobenzylidene)amino-4H-1,2,4-triazole)-bis((E)-4-(chlor obenzylidene)amino-4H-1,2,4-triazole)-di-copper(i) diperchlorate naphthalene clathrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H28 Cl4 Cu2 N16, 2(Cl O4), 2(C10 H8)' _chemical_formula_sum 'C56 H44 Cl6 Cu2 N16 O8' _chemical_formula_weight 1408.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.023(2) _cell_length_b 18.472(3) _cell_length_c 22.101(4) _cell_angle_alpha 90 _cell_angle_beta 95.36(3) _cell_angle_gamma 90 _cell_volume 2854.6(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2156 _cell_measurement_theta_min 2.8719 _cell_measurement_theta_max 28.7013 _cell_oxdiff_twin_number 2 loop_ _cell_oxdiff_twin_id _cell_oxdiff_twin_matrix_11 _cell_oxdiff_twin_matrix_12 _cell_oxdiff_twin_matrix_13 _cell_oxdiff_twin_matrix_21 _cell_oxdiff_twin_matrix_22 _cell_oxdiff_twin_matrix_23 _cell_oxdiff_twin_matrix_31 _cell_oxdiff_twin_matrix_32 _cell_oxdiff_twin_matrix_33 1 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000 2 1.0003 -0.0002 -0.0001 -0.0033 -0.9995 -0.0008 -0.5795 -0.0004 -0.9985 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.639 _exptl_crystal_F_000 1432 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_absorpt_coefficient_mu 1.098 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13567 _diffrn_reflns_av_unetI/netI 0.4632 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.880 _diffrn_reflns_theta_max 28.810 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.957 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.957 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.957 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 13567 _reflns_number_gt 4762 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . loop_ _diffrn_oxdiff_twin_id _diffrn_oxdiff_twin_ratio _diffrn_oxdiff_twin_reflns_isolated _diffrn_oxdiff_twin_reflns_overlapped 1 0.5665 1362 22416 2 0.4335 1361 22416 _reflns_special_details ; _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_structure_solution ; SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.) ; _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refined as a 2-component twin. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0680P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 13567 _refine_ls_number_parameters 398 _refine_ls_number_restraints 78 _refine_ls_R_factor_all 0.2903 _refine_ls_R_factor_gt 0.1199 _refine_ls_wR_factor_ref 0.2289 _refine_ls_wR_factor_gt 0.1754 _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_restrained_S_all 0.928 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5377(2) 0.06918(9) 0.94827(7) 0.0174(4) Uani 1 1 d . . . . . Cl5 Cl 0.9052(6) -0.39007(19) 0.60954(14) 0.0265(10) Uani 1 1 d . . . . . Cl25 Cl 0.9185(5) 0.4284(2) 0.53552(13) 0.0236(9) Uani 1 1 d . . . . . N1 N 0.5832(15) -0.0317(5) 0.9293(4) 0.013(2) Uani 1 1 d . U . . . N2 N 0.5704(15) -0.0862(5) 0.9721(4) 0.015(2) Uani 1 1 d . U . . . N3 N 0.6539(15) -0.1337(6) 0.8876(5) 0.016(3) Uani 1 1 d . . . . . N4 N 0.7013(16) -0.1904(5) 0.8486(4) 0.017(3) Uani 1 1 d . U . . . N11 N 0.5997(15) 0.1578(5) 0.9096(4) 0.013(3) Uani 1 1 d . . . . . N12 N 0.6283(15) 0.2223(5) 0.9441(5) 0.018(3) Uani 1 1 d . . . . . N13 N 0.6757(15) 0.2440(5) 0.8488(4) 0.012(3) Uani 1 1 d . . . . . N14 N 0.7199(15) 0.2866(6) 0.8001(5) 0.016(3) Uani 1 1 d . . . . . C1 C 0.719(2) -0.1745(7) 0.7942(5) 0.016(3) Uani 1 1 d . U . . . H1A H 0.6997 -0.1256 0.7817 0.020 Uiso 1 1 calc R U . . . C2 C 0.7673(19) -0.2268(7) 0.7495(6) 0.016(3) Uani 1 1 d . U . . . C3 C 0.7983(18) -0.2988(7) 0.7665(5) 0.017(3) Uani 1 1 d . . . . . H3A H 0.7883 -0.3132 0.8074 0.021 Uiso 1 1 calc R U . . . C4 C 0.8448(19) -0.3503(7) 0.7229(5) 0.018(3) Uani 1 1 d . . . . . H4A H 0.8686 -0.3994 0.7341 0.022 Uiso 1 1 calc R U . . . C5 C 0.8548(19) -0.3281(8) 0.6649(6) 0.024(4) Uani 1 1 d . . . . . C6 C 0.820(2) -0.2567(7) 0.6476(5) 0.018(3) Uani 1 1 d . U . . . H6A H 0.8230 -0.2426 0.6063 0.022 Uiso 1 1 calc R U . . . C7 C 0.7815(18) -0.2068(7) 0.6905(5) 0.016(3) Uani 1 1 d . U . . . H7A H 0.7642 -0.1574 0.6792 0.019 Uiso 1 1 calc R U . . . C8 C 0.6316(17) -0.0619(7) 0.8793(5) 0.015(3) Uani 1 1 d . U . . . H8A H 0.6484 -0.0369 0.8426 0.018 Uiso 1 1 calc R U . . . C9 C 0.6151(16) -0.1451(7) 0.9447(5) 0.012(3) Uani 1 1 d . . . . . H9A H 0.6198 -0.1915 0.9634 0.014 Uiso 1 1 calc R U . . . C11 C 0.7251(19) 0.2559(7) 0.7490(5) 0.012(3) Uani 1 1 d . U . . . H11A H 0.7005 0.2055 0.7443 0.014 Uiso 1 1 calc R U . . . C12 C 0.7695(18) 0.2998(7) 0.6975(5) 0.014(3) Uani 1 1 d . U . . . C13 C 0.808(2) 0.3729(6) 0.7031(5) 0.018(3) Uani 1 1 d . . . . . H13A H 0.8054 0.3959 0.7415 0.021 Uiso 1 1 calc R U . . . C14 C 0.8503(17) 0.4135(7) 0.6527(5) 0.014(3) Uani 1 1 d . U . . . H14A H 0.8706 0.4642 0.6561 0.017 Uiso 1 1 calc R U . . . C15 C 0.8619(17) 0.3792(7) 0.5989(5) 0.011(2) Uani 1 1 d . U . . . C16 C 0.8302(17) 0.3063(7) 0.5915(5) 0.013(3) Uani 1 1 d . U . . . H16A H 0.8405 0.2834 0.5534 0.015 Uiso 1 1 calc R U . . . C17 C 0.782(2) 0.2668(7) 0.6416(5) 0.019(3) Uani 1 1 d . . . . . H17A H 0.7577 0.2164 0.6374 0.023 Uiso 1 1 calc R U . . . C18 C 0.6266(19) 0.1744(7) 0.8538(6) 0.022(4) Uani 1 1 d . . . . . H18A H 0.6130 0.1413 0.8208 0.026 Uiso 1 1 calc R U . . . C19 C 0.676(2) 0.2707(7) 0.9055(6) 0.025(4) Uani 1 1 d . . . . . H19A H 0.7084 0.3193 0.9162 0.030 Uiso 1 1 calc R U . . . C41 C 0.258(2) 0.1221(8) 0.4570(6) 0.032(4) Uani 1 1 d . . . . . H41A H 0.3321 0.1200 0.4232 0.039 Uiso 1 1 calc R U . . . C42 C 0.333(2) 0.1514(7) 0.5105(6) 0.036(5) Uani 1 1 d . . . . . H42A H 0.4604 0.1689 0.5142 0.044 Uiso 1 1 calc R U . . . C43 C 0.225(3) 0.1563(8) 0.5597(7) 0.044(4) Uani 1 1 d . U . . . H43A H 0.2758 0.1804 0.5956 0.053 Uiso 1 1 calc R U . . . C44 C 0.045(2) 0.1268(7) 0.5575(7) 0.039(4) Uani 1 1 d . U . . . H44A H -0.0225 0.1262 0.5928 0.047 Uiso 1 1 calc R U . . . C45 C -0.226(3) 0.0661(8) 0.4999(8) 0.048(5) Uani 1 1 d . . . . . H45A H -0.2957 0.0664 0.5346 0.057 Uiso 1 1 calc R U . . . C46 C -0.303(2) 0.0364(8) 0.4483(8) 0.038(4) Uani 1 1 d . . . . . H46A H -0.4271 0.0158 0.4467 0.045 Uiso 1 1 calc R U . . . C47 C -0.203(3) 0.0352(8) 0.3968(7) 0.042(5) Uani 1 1 d . . . . . H47A H -0.2616 0.0147 0.3603 0.050 Uiso 1 1 calc R U . . . C48 C -0.022(2) 0.0629(8) 0.3977(7) 0.044(5) Uani 1 1 d . . . . . H48A H 0.0456 0.0615 0.3625 0.053 Uiso 1 1 calc R U . . . C49 C 0.060(3) 0.0934(8) 0.4520(7) 0.040(4) Uani 1 1 d . . . . . C50 C -0.037(3) 0.0978(8) 0.5037(7) 0.035(4) Uani 1 1 d . . . . . Cl1 Cl 0.6816(6) 0.4699(2) 0.21717(16) 0.0312(10) Uani 1 1 d . . . . . O1 O 0.737(2) 0.4136(6) 0.1822(5) 0.088(5) Uani 1 1 d . . . . . O2 O 0.523(2) 0.4483(8) 0.2494(6) 0.115(6) Uani 1 1 d . . . . . O3 O 0.828(2) 0.4897(7) 0.2617(5) 0.092(5) Uani 1 1 d . . . . . O4 O 0.6218(16) 0.5289(6) 0.1808(5) 0.058(3) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0227(10) 0.0142(9) 0.0160(8) 0.0011(8) 0.0051(8) -0.0012(10) Cl5 0.037(3) 0.021(2) 0.0233(19) -0.0084(16) 0.0083(18) 0.0021(19) Cl25 0.022(2) 0.030(2) 0.0195(18) 0.0090(16) 0.0042(15) -0.005(2) N1 0.012(5) 0.010(5) 0.017(4) -0.006(4) 0.002(4) -0.005(4) N2 0.013(5) 0.011(5) 0.023(5) 0.001(4) 0.004(4) -0.007(5) N3 0.008(7) 0.020(7) 0.021(6) -0.009(5) -0.001(5) 0.003(5) N4 0.028(7) 0.010(6) 0.013(5) -0.003(5) -0.001(5) -0.001(6) N11 0.022(7) 0.011(6) 0.007(5) -0.004(5) -0.002(5) -0.007(5) N12 0.024(7) 0.007(6) 0.025(6) 0.004(5) 0.008(6) -0.001(5) N13 0.005(6) 0.012(6) 0.019(6) 0.002(5) 0.007(5) -0.001(5) N14 0.019(7) 0.011(6) 0.018(6) 0.011(5) 0.001(5) -0.003(6) C1 0.023(7) 0.006(6) 0.020(6) -0.001(5) -0.007(6) 0.006(6) C2 0.014(5) 0.014(5) 0.019(5) 0.003(4) -0.002(4) -0.006(5) C3 0.011(8) 0.023(8) 0.019(7) 0.001(6) 0.001(6) 0.011(7) C4 0.017(9) 0.019(8) 0.019(7) -0.002(6) 0.000(7) -0.008(7) C5 0.017(9) 0.031(10) 0.023(8) -0.015(7) 0.001(7) 0.007(8) C6 0.016(7) 0.025(8) 0.013(7) 0.002(6) 0.002(6) 0.000(7) C7 0.015(7) 0.016(6) 0.017(6) 0.010(5) -0.002(5) 0.000(6) C8 0.020(6) 0.010(6) 0.015(5) -0.002(5) 0.000(5) -0.004(5) C9 0.002(7) 0.018(8) 0.014(7) 0.006(6) -0.002(6) -0.001(6) C11 0.010(6) 0.006(6) 0.019(6) 0.004(5) -0.002(5) -0.002(5) C12 0.012(5) 0.008(5) 0.019(5) 0.004(4) -0.003(4) -0.001(4) C13 0.028(9) 0.008(8) 0.017(7) 0.003(6) 0.002(7) -0.001(7) C14 0.012(6) 0.016(6) 0.013(5) 0.008(5) -0.003(5) -0.001(5) C15 0.009(4) 0.015(4) 0.009(4) 0.008(4) 0.000(4) 0.000(4) C16 0.008(6) 0.019(6) 0.011(5) 0.005(5) 0.001(5) 0.001(5) C17 0.015(8) 0.014(8) 0.028(8) -0.002(6) -0.003(7) -0.004(7) C18 0.021(9) 0.018(9) 0.025(8) 0.002(7) -0.010(7) 0.002(7) C19 0.024(10) 0.013(8) 0.037(9) 0.000(7) -0.004(8) -0.003(7) C41 0.047(11) 0.030(10) 0.025(9) 0.016(7) 0.026(9) 0.013(9) C42 0.051(13) 0.018(9) 0.045(10) 0.014(8) 0.031(9) 0.016(8) C43 0.082(12) 0.020(8) 0.035(8) -0.010(7) 0.035(9) -0.008(8) C44 0.071(12) 0.009(8) 0.044(8) 0.003(7) 0.041(9) -0.003(7) C45 0.062(14) 0.027(9) 0.057(11) 0.021(10) 0.025(10) 0.007(12) C46 0.028(11) 0.024(9) 0.065(11) 0.021(9) 0.025(10) 0.012(8) C47 0.051(13) 0.025(10) 0.046(10) 0.009(8) -0.016(10) -0.009(9) C48 0.048(12) 0.029(10) 0.057(11) 0.021(9) 0.014(9) 0.006(10) C49 0.056(12) 0.028(9) 0.038(10) 0.012(8) 0.005(10) 0.017(10) C50 0.044(12) 0.016(9) 0.048(11) 0.005(8) 0.017(9) 0.004(9) Cl1 0.044(3) 0.025(2) 0.025(2) 0.0040(18) 0.000(2) -0.001(2) O1 0.149(15) 0.041(9) 0.068(8) -0.031(6) -0.017(9) 0.033(9) O2 0.067(11) 0.144(14) 0.140(12) 0.101(11) 0.035(10) 0.004(11) O3 0.072(10) 0.125(12) 0.069(8) -0.064(8) -0.046(8) 0.052(10) O4 0.035(8) 0.044(8) 0.093(8) 0.036(7) 0.002(7) 0.003(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N11 1.915(10) . ? Cu1 N1 1.943(10) . ? Cu1 N2 2.005(10) 3_657 ? Cl5 C5 1.737(13) . ? Cl25 C15 1.747(11) . ? N1 C8 1.311(13) . ? N1 N2 1.391(12) . ? N2 C9 1.298(13) . ? N2 Cu1 2.005(10) 3_657 ? N3 C9 1.331(13) . ? N3 C8 1.346(15) . ? N3 N4 1.416(13) . ? N4 C1 1.256(13) . ? N11 C18 1.302(14) . ? N11 N12 1.419(12) . ? N12 C19 1.300(14) . ? N13 C18 1.337(14) . ? N13 C19 1.348(14) . ? N13 N14 1.391(12) . ? N14 C11 1.268(14) . ? C1 C2 1.444(16) . ? C1 H1A 0.9500 . ? C2 C7 1.368(15) . ? C2 C3 1.393(16) . ? C3 C4 1.414(16) . ? C3 H3A 0.9500 . ? C4 C5 1.354(16) . ? C4 H4A 0.9500 . ? C5 C6 1.389(17) . ? C6 C7 1.368(15) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C11 C12 1.453(16) . ? C11 H11A 0.9500 . ? C12 C13 1.381(15) . ? C12 C17 1.389(15) . ? C13 C14 1.397(14) . ? C13 H13A 0.9500 . ? C14 C15 1.357(15) . ? C14 H14A 0.9500 . ? C15 C16 1.373(15) . ? C16 C17 1.394(15) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C41 C42 1.360(18) . ? C41 C49 1.48(2) . ? C41 H41A 0.9500 . ? C42 C43 1.387(17) . ? C42 H42A 0.9500 . ? C43 C44 1.37(2) . ? C43 H43A 0.9500 . ? C44 C50 1.381(19) . ? C44 H44A 0.9500 . ? C45 C46 1.335(19) . ? C45 C50 1.44(2) . ? C45 H45A 0.9500 . ? C46 C47 1.391(19) . ? C46 H46A 0.9500 . ? C47 C48 1.37(2) . ? C47 H47A 0.9500 . ? C48 C49 1.40(2) . ? C48 H48A 0.9500 . ? C49 C50 1.389(19) . ? Cl1 O1 1.376(10) . ? Cl1 O4 1.394(10) . ? Cl1 O3 1.403(11) . ? Cl1 O2 1.432(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N11 Cu1 N1 132.4(4) . . ? N11 Cu1 N2 112.2(4) . 3_657 ? N1 Cu1 N2 115.0(4) . 3_657 ? C8 N1 N2 107.7(10) . . ? C8 N1 Cu1 130.6(9) . . ? N2 N1 Cu1 121.7(7) . . ? C9 N2 N1 104.8(9) . . ? C9 N2 Cu1 132.0(8) . 3_657 ? N1 N2 Cu1 122.5(7) . 3_657 ? C9 N3 C8 104.7(10) . . ? C9 N3 N4 122.7(11) . . ? C8 N3 N4 132.5(10) . . ? C1 N4 N3 117.4(10) . . ? C18 N11 N12 106.5(10) . . ? C18 N11 Cu1 133.1(9) . . ? N12 N11 Cu1 120.4(7) . . ? C19 N12 N11 104.9(10) . . ? C18 N13 C19 104.6(11) . . ? C18 N13 N14 133.3(11) . . ? C19 N13 N14 122.1(11) . . ? C11 N14 N13 117.6(11) . . ? N4 C1 C2 123.3(12) . . ? N4 C1 H1A 118.3 . . ? C2 C1 H1A 118.3 . . ? C7 C2 C3 119.5(12) . . ? C7 C2 C1 120.8(12) . . ? C3 C2 C1 119.6(11) . . ? C2 C3 C4 119.9(12) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C5 C4 C3 118.5(13) . . ? C5 C4 H4A 120.8 . . ? C3 C4 H4A 120.8 . . ? C4 C5 C6 121.7(12) . . ? C4 C5 Cl5 120.0(11) . . ? C6 C5 Cl5 118.3(10) . . ? C7 C6 C5 119.4(12) . . ? C7 C6 H6A 120.3 . . ? C5 C6 H6A 120.3 . . ? C2 C7 C6 121.0(12) . . ? C2 C7 H7A 119.5 . . ? C6 C7 H7A 119.5 . . ? N1 C8 N3 109.8(11) . . ? N1 C8 H8A 125.1 . . ? N3 C8 H8A 125.1 . . ? N2 C9 N3 113.0(11) . . ? N2 C9 H9A 123.5 . . ? N3 C9 H9A 123.5 . . ? N14 C11 C12 118.3(12) . . ? N14 C11 H11A 120.9 . . ? C12 C11 H11A 120.9 . . ? C13 C12 C17 118.7(12) . . ? C13 C12 C11 122.1(12) . . ? C17 C12 C11 119.2(12) . . ? C12 C13 C14 120.6(12) . . ? C12 C13 H13A 119.7 . . ? C14 C13 H13A 119.7 . . ? C15 C14 C13 118.9(12) . . ? C15 C14 H14A 120.6 . . ? C13 C14 H14A 120.6 . . ? C14 C15 C16 122.8(11) . . ? C14 C15 Cl25 119.7(10) . . ? C16 C15 Cl25 117.5(9) . . ? C15 C16 C17 117.8(11) . . ? C15 C16 H16A 121.1 . . ? C17 C16 H16A 121.1 . . ? C12 C17 C16 121.2(12) . . ? C12 C17 H17A 119.4 . . ? C16 C17 H17A 119.4 . . ? N11 C18 N13 111.6(12) . . ? N11 C18 H18A 124.2 . . ? N13 C18 H18A 124.2 . . ? N12 C19 N13 112.3(12) . . ? N12 C19 H19A 123.8 . . ? N13 C19 H19A 123.8 . . ? C42 C41 C49 119.3(14) . . ? C42 C41 H41A 120.3 . . ? C49 C41 H41A 120.3 . . ? C41 C42 C43 120.9(16) . . ? C41 C42 H42A 119.6 . . ? C43 C42 H42A 119.6 . . ? C44 C43 C42 121.0(15) . . ? C44 C43 H43A 119.5 . . ? C42 C43 H43A 119.5 . . ? C43 C44 C50 119.7(14) . . ? C43 C44 H44A 120.2 . . ? C50 C44 H44A 120.2 . . ? C46 C45 C50 120.9(16) . . ? C46 C45 H45A 119.5 . . ? C50 C45 H45A 119.5 . . ? C45 C46 C47 120.7(16) . . ? C45 C46 H46A 119.7 . . ? C47 C46 H46A 119.7 . . ? C48 C47 C46 121.4(16) . . ? C48 C47 H47A 119.3 . . ? C46 C47 H47A 119.3 . . ? C47 C48 C49 118.2(16) . . ? C47 C48 H48A 120.9 . . ? C49 C48 H48A 120.9 . . ? C50 C49 C48 122.0(17) . . ? C50 C49 C41 116.8(15) . . ? C48 C49 C41 121.2(15) . . ? C44 C50 C49 122.1(17) . . ? C44 C50 C45 121.0(16) . . ? C49 C50 C45 116.8(15) . . ? O1 Cl1 O4 110.7(7) . . ? O1 Cl1 O3 111.3(8) . . ? O4 Cl1 O3 111.3(8) . . ? O1 Cl1 O2 110.1(9) . . ? O4 Cl1 O2 107.4(8) . . ? O3 Cl1 O2 105.9(8) . . ? 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 C8 N1 N2 C9 0.9(13) . . . . ? Cu1 N1 N2 C9 -178.0(8) . . . . ? C8 N1 N2 Cu1 -170.5(8) . . . 3_657 ? Cu1 N1 N2 Cu1 10.5(13) . . . 3_657 ? C9 N3 N4 C1 174.0(13) . . . . ? C8 N3 N4 C1 -4(2) . . . . ? C18 N11 N12 C19 -2.3(14) . . . . ? Cu1 N11 N12 C19 177.0(9) . . . . ? C18 N13 N14 C11 -4(2) . . . . ? C19 N13 N14 C11 176.5(13) . . . . ? N3 N4 C1 C2 179.8(11) . . . . ? N4 C1 C2 C7 178.8(14) . . . . ? N4 C1 C2 C3 -1(2) . . . . ? C7 C2 C3 C4 0.3(19) . . . . ? C1 C2 C3 C4 179.7(13) . . . . ? C2 C3 C4 C5 -1.1(19) . . . . ? C3 C4 C5 C6 0(2) . . . . ? C3 C4 C5 Cl5 -178.3(10) . . . . ? C4 C5 C6 C7 2(2) . . . . ? Cl5 C5 C6 C7 -179.5(11) . . . . ? C3 C2 C7 C6 2(2) . . . . ? C1 C2 C7 C6 -177.5(13) . . . . ? C5 C6 C7 C2 -3(2) . . . . ? N2 N1 C8 N3 -0.9(14) . . . . ? Cu1 N1 C8 N3 177.9(9) . . . . ? C9 N3 C8 N1 0.5(14) . . . . ? N4 N3 C8 N1 178.7(12) . . . . ? N1 N2 C9 N3 -0.7(14) . . . . ? Cu1 N2 C9 N3 169.7(8) 3_657 . . . ? C8 N3 C9 N2 0.1(14) . . . . ? N4 N3 C9 N2 -178.3(11) . . . . ? N13 N14 C11 C12 179.5(11) . . . . ? N14 C11 C12 C13 1(2) . . . . ? N14 C11 C12 C17 177.9(13) . . . . ? C17 C12 C13 C14 3(2) . . . . ? C11 C12 C13 C14 179.9(12) . . . . ? C12 C13 C14 C15 -3(2) . . . . ? C13 C14 C15 C16 1(2) . . . . ? C13 C14 C15 Cl25 -179.0(10) . . . . ? C14 C15 C16 C17 0.7(19) . . . . ? Cl25 C15 C16 C17 -179.1(10) . . . . ? C13 C12 C17 C16 -1(2) . . . . ? C11 C12 C17 C16 -178.0(12) . . . . ? C15 C16 C17 C12 -0.9(19) . . . . ? N12 N11 C18 N13 1.8(15) . . . . ? Cu1 N11 C18 N13 -177.4(9) . . . . ? C19 N13 C18 N11 -0.6(16) . . . . ? N14 N13 C18 N11 179.5(12) . . . . ? N11 N12 C19 N13 2.0(15) . . . . ? C18 N13 C19 N12 -1.0(16) . . . . ? N14 N13 C19 N12 179.0(11) . . . . ? C49 C41 C42 C43 -1(2) . . . . ? C41 C42 C43 C44 5(2) . . . . ? C42 C43 C44 C50 -6(2) . . . . ? C50 C45 C46 C47 0(2) . . . . ? C45 C46 C47 C48 1(2) . . . . ? C46 C47 C48 C49 -1(2) . . . . ? C47 C48 C49 C50 -2(2) . . . . ? C47 C48 C49 C41 177.8(13) . . . . ? C42 C41 C49 C50 -1(2) . . . . ? C42 C41 C49 C48 179.8(13) . . . . ? C43 C44 C50 C49 4(2) . . . . ? C43 C44 C50 C45 179.7(14) . . . . ? C48 C49 C50 C44 178.9(14) . . . . ? C41 C49 C50 C44 -1(2) . . . . ? C48 C49 C50 C45 3(2) . . . . ? C41 C49 C50 C45 -176.5(13) . . . . ? C46 C45 C50 C44 -178.1(13) . . . . ? C46 C45 C50 C49 -2(2) . . . . ? _refine_diff_density_max 0.751 _refine_diff_density_min -1.024 _refine_diff_density_rms 0.176 #====== END # start Validation Reply Form _vrf_PLAT021_1-C10H8 ; PROBLEM: Ratio Unique / Expected Reflections too High ... 1.819 RESPONSE: The structure was refined as two component twin, BASF 0.41 ; _database_code_depnum_ccdc_archive 'CCDC 949086' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1-C8H10 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; bis(\m~2~-4-(E)-(4-chlorobenzylidene)amino-4H-1,2,4-triazole)-bis((E)-4-(chlor obenzylidene)amino-4H-1,2,4-triazole)-di-copper(i) diperchlorate xylene disolvate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H28 Cl4 Cu2 N16, 2(Cl O4), 2(C8 H10)' _chemical_formula_sum 'C52 H48 Cl6 Cu2 N16 O8' _chemical_formula_weight 1364.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.993(2) _cell_length_b 18.663(3) _cell_length_c 22.010(4) _cell_angle_alpha 90 _cell_angle_beta 95.07(3) _cell_angle_gamma 90 _cell_volume 2861.3(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5133 _cell_measurement_theta_min 2.7792 _cell_measurement_theta_max 36.8569 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_F_000 1392 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_absorpt_coefficient_mu 1.092 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 50499 _diffrn_reflns_av_unetI/netI 0.1944 _diffrn_reflns_av_R_equivalents 0.1569 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.867 _diffrn_reflns_theta_max 36.962 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.936 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.936 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.936 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 13575 _reflns_number_gt 5558 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET) (compiled Aug 14 2012,18:12:40) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET) (compiled Aug 14 2012,18:12:40) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET) (compiled Aug 14 2012,18:12:40) ; _computing_structure_solution ; SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.) ; _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Ratio of particular components of the disordered xylene molecules were refined assuming that sum of all the components is equal to 1 ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+4.7914P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 13575 _refine_ls_number_parameters 528 _refine_ls_number_restraints 688 _refine_ls_R_factor_all 0.2566 _refine_ls_R_factor_gt 0.1132 _refine_ls_wR_factor_ref 0.2269 _refine_ls_wR_factor_gt 0.1762 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.010 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.45931(8) -0.06906(3) 0.05192(2) 0.02446(14) Uani 1 1 d . . . . . Cl5 Cl 0.09754(19) 0.38631(7) 0.39442(6) 0.0421(3) Uani 1 1 d . . . . . Cl15 Cl 0.07853(16) -0.43095(7) 0.46328(5) 0.0314(2) Uani 1 1 d . . . . . N1 N 0.4162(5) 0.03037(19) 0.07198(15) 0.0236(7) Uani 1 1 d . . . . . N2 N 0.4331(5) 0.08488(18) 0.02947(16) 0.0242(7) Uani 1 1 d . . . . . N3 N 0.3508(5) 0.13165(19) 0.11404(15) 0.0238(7) Uani 1 1 d . . . . . N4 N 0.3041(5) 0.1881(2) 0.15273(16) 0.0267(8) Uani 1 1 d . . . . . N11 N 0.4033(5) -0.1606(2) 0.08829(16) 0.0268(8) Uani 1 1 d . . . . . N12 N 0.3894(6) -0.2225(2) 0.05378(17) 0.0331(9) Uani 1 1 d . . . . . N13 N 0.3250(5) -0.2468(2) 0.14730(16) 0.0268(8) Uani 1 1 d . . . . . N14 N 0.2798(6) -0.2919(2) 0.19486(17) 0.0305(9) Uani 1 1 d . . . . . C1 C 0.2838(6) 0.1709(3) 0.2076(2) 0.0288(10) Uani 1 1 d . . . . . H1A H 0.2984 0.1223 0.2199 0.035 Uiso 1 1 calc R U . . . C2 C 0.2378(6) 0.2254(3) 0.2524(2) 0.0302(10) Uani 1 1 d . . . . . C3 C 0.2139(7) 0.2975(3) 0.2370(2) 0.0348(11) Uani 1 1 d . . . . . H3A H 0.2292 0.3126 0.1965 0.042 Uiso 1 1 calc R U . . . C4 C 0.1678(8) 0.3473(3) 0.2801(2) 0.0371(11) Uani 1 1 d . . . . . H4A H 0.1498 0.3963 0.2694 0.044 Uiso 1 1 calc R U . . . C5 C 0.1486(7) 0.3241(3) 0.3391(2) 0.0354(11) Uani 1 1 d . . . . . C6 C 0.1716(7) 0.2528(3) 0.3554(2) 0.0341(11) Uani 1 1 d . . . . . H6A H 0.1568 0.2379 0.3960 0.041 Uiso 1 1 calc R U . . . C7 C 0.2166(7) 0.2032(3) 0.3117(2) 0.0321(10) Uani 1 1 d . . . . . H7A H 0.2328 0.1541 0.3224 0.039 Uiso 1 1 calc R U . . . C8 C 0.3650(6) 0.0599(2) 0.12244(19) 0.0256(9) Uani 1 1 d . . . . . H8A H 0.3418 0.0350 0.1587 0.031 Uiso 1 1 calc R U . . . C9 C 0.3930(6) 0.1448(2) 0.05607(19) 0.0260(9) Uani 1 1 d . . . . . H9A H 0.3933 0.1908 0.0376 0.031 Uiso 1 1 calc R U . . . C11 C 0.2673(6) -0.2617(2) 0.2463(2) 0.0276(9) Uani 1 1 d . . . . . H11A H 0.2878 -0.2116 0.2505 0.033 Uiso 1 1 calc R U . . . C12 C 0.2210(6) -0.3046(2) 0.2988(2) 0.0276(9) Uani 1 1 d . . . . . C13 C 0.1872(7) -0.3781(3) 0.2944(2) 0.0316(10) Uani 1 1 d . . . . . H13A H 0.1942 -0.4018 0.2564 0.038 Uiso 1 1 calc R U . . . C14 C 0.1434(7) -0.4168(2) 0.3450(2) 0.0301(10) Uani 1 1 d . . . . . H14A H 0.1205 -0.4669 0.3420 0.036 Uiso 1 1 calc R U . . . C15 C 0.1334(6) -0.3819(2) 0.39969(19) 0.0252(9) Uani 1 1 d . . . . . C16 C 0.1659(7) -0.3090(3) 0.4057(2) 0.0310(10) Uani 1 1 d . . . . . H16A H 0.1589 -0.2858 0.4438 0.037 Uiso 1 1 calc R U . . . C17 C 0.2091(7) -0.2705(3) 0.3546(2) 0.0315(10) Uani 1 1 d . . . . . H17A H 0.2307 -0.2203 0.3579 0.038 Uiso 1 1 calc R U . . . C18 C 0.3659(6) -0.1760(2) 0.1440(2) 0.0271(9) Uani 1 1 d . . . . . H18A H 0.3671 -0.1429 0.1768 0.033 Uiso 1 1 calc R U . . . C19 C 0.3418(7) -0.2731(3) 0.0902(2) 0.0345(11) Uani 1 1 d . . . . . H19A H 0.3216 -0.3218 0.0787 0.041 Uiso 1 1 calc R U . . . Cl1 Cl 0.3384(5) -0.03208(11) 0.28019(8) 0.0435(8) Uani 0.794(9) 1 d D U P . . O1 O 0.2936(11) -0.0984(3) 0.3083(3) 0.074(2) Uani 0.595(3) 1 d D U P A . O2 O 0.1735(8) -0.0092(4) 0.2405(3) 0.0619(17) Uani 0.595(3) 1 d D U P A . O3 O 0.3795(10) 0.0216(3) 0.3260(3) 0.0594(18) Uani 0.595(3) 1 d D U P A . O4 O 0.4979(8) -0.0407(4) 0.2445(3) 0.0678(19) Uani 0.595(3) 1 d D U P A . O21 O 0.386(3) -0.0956(9) 0.3172(8) 0.066(3) Uani 0.212(3) 1 d D U P A . O22 O 0.198(2) -0.0507(10) 0.2300(7) 0.054(3) Uani 0.212(3) 1 d D U P A . O23 O 0.261(3) 0.0231(8) 0.3178(8) 0.066(3) Uani 0.212(3) 1 d D U P A . O24 O 0.512(2) -0.0055(9) 0.2557(7) 0.061(3) Uani 0.212(3) 1 d D U P A . Cl11 Cl 0.2622(15) -0.0409(5) 0.2821(4) 0.0600(18) Uani 0.206(9) 1 d D U P A 3 O31 O 0.400(3) -0.0970(11) 0.3005(10) 0.067(3) Uani 0.193(3) 1 d D U P A 3 O32 O 0.213(3) -0.0448(11) 0.2166(8) 0.051(3) Uani 0.193(3) 1 d D U P A 3 O33 O 0.347(3) 0.0286(10) 0.2976(9) 0.058(3) Uani 0.193(3) 1 d D U P A 3 O34 O 0.090(3) -0.0505(10) 0.3137(8) 0.075(3) Uani 0.193(3) 1 d D U P A 3 C21 C 0.131(2) 0.5504(7) 0.0784(6) 0.083(2) Uani 0.715(7) 1 d D U P B 1 C22 C -0.0286(18) 0.5862(6) 0.0523(5) 0.075(2) Uani 0.715(7) 1 d . U P B 1 H22A H -0.1386 0.5889 0.0746 0.090 Uiso 0.715(7) 1 calc R U P B 1 C23 C -0.0378(18) 0.6185(6) -0.0047(6) 0.085(2) Uani 0.715(7) 1 d D U P B 1 C24 C 0.130(2) 0.6111(7) -0.0365(6) 0.085(2) Uani 0.715(7) 1 d . U P B 1 H24A H 0.1286 0.6317 -0.0760 0.102 Uiso 0.715(7) 1 calc R U P B 1 C25 C 0.2845(19) 0.5779(6) -0.0145(6) 0.084(2) Uani 0.715(7) 1 d . U P B 1 H25A H 0.3922 0.5759 -0.0379 0.100 Uiso 0.715(7) 1 calc R U P B 1 C26 C 0.2945(19) 0.5469(6) 0.0398(6) 0.083(2) Uani 0.715(7) 1 d . U P B 1 H26 H 0.4080 0.5220 0.0543 0.100 Uiso 0.715(7) 1 calc R U P B 1 C27 C 0.128(2) 0.5156(6) 0.1360(5) 0.092(3) Uani 0.715(7) 1 d D U P B 1 H27A H 0.0057 0.5249 0.1529 0.137 Uiso 0.715(7) 1 calc R U P B 1 H27B H 0.2336 0.5341 0.1640 0.137 Uiso 0.715(7) 1 calc R U P B 1 H27C H 0.1445 0.4639 0.1307 0.137 Uiso 0.715(7) 1 calc R U P B 1 C28 C -0.2091(19) 0.6556(7) -0.0260(7) 0.098(3) Uani 0.715(7) 1 d D U P B 1 H28A H -0.1951 0.6753 -0.0666 0.147 Uiso 0.715(7) 1 calc R U P B 1 H28B H -0.2319 0.6948 0.0022 0.147 Uiso 0.715(7) 1 calc R U P B 1 H28C H -0.3179 0.6224 -0.0281 0.147 Uiso 0.715(7) 1 calc R U P B 1 C31 C 0.106(3) 0.5611(13) 0.0626(9) 0.085(3) Uani 0.285(7) 1 d DG U P B 2 C32 C -0.078(3) 0.5807(13) 0.0760(8) 0.084(3) Uani 0.285(7) 1 d G U P B 2 H32A H -0.1195 0.5698 0.1149 0.101 Uiso 0.285(7) 1 calc R U P B 2 C33 C -0.199(2) 0.6162(11) 0.0327(10) 0.086(3) Uani 0.285(7) 1 d G U P B 2 H33A H -0.3247 0.6296 0.0419 0.103 Uiso 0.285(7) 1 calc R U P B 2 C34 C -0.138(3) 0.6322(13) -0.0241(9) 0.090(3) Uani 0.285(7) 1 d DG U P B 2 C35 C 0.045(3) 0.6127(13) -0.0376(8) 0.086(3) Uani 0.285(7) 1 d G U P B 2 H35A H 0.0873 0.6236 -0.0764 0.103 Uiso 0.285(7) 1 calc R U P B 2 C36 C 0.167(2) 0.5771(12) 0.0057(10) 0.083(2) Uani 0.285(7) 1 d G U P B 2 H36A H 0.2925 0.5637 -0.0035 0.100 Uiso 0.285(7) 1 calc R U P B 2 C37 C 0.273(3) 0.5315(16) 0.0947(14) 0.089(3) Uani 0.285(7) 1 d D U P B 2 H37A H 0.2451 0.5181 0.1360 0.134 Uiso 0.285(7) 1 calc R U P B 2 H37B H 0.3769 0.5670 0.0969 0.134 Uiso 0.285(7) 1 calc R U P B 2 H37C H 0.3136 0.4888 0.0731 0.134 Uiso 0.285(7) 1 calc R U P B 2 C38 C -0.306(4) 0.6569(18) -0.0591(15) 0.101(4) Uani 0.285(7) 1 d D U P B 2 H38A H -0.2745 0.6696 -0.1002 0.152 Uiso 0.285(7) 1 calc R U P B 2 H38B H -0.3567 0.6992 -0.0394 0.152 Uiso 0.285(7) 1 calc R U P B 2 H38C H -0.4036 0.6190 -0.0617 0.152 Uiso 0.285(7) 1 calc R U P B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0289(3) 0.0254(3) 0.0199(2) 0.0006(2) 0.00719(19) -0.0008(2) Cl5 0.0417(7) 0.0480(8) 0.0378(7) -0.0210(6) 0.0106(5) 0.0016(6) Cl15 0.0298(6) 0.0402(6) 0.0250(5) 0.0098(5) 0.0075(4) -0.0021(5) N1 0.0262(19) 0.0262(19) 0.0189(17) 0.0021(14) 0.0046(14) -0.0027(15) N2 0.0259(19) 0.0240(19) 0.0233(17) 0.0017(14) 0.0063(14) -0.0040(14) N3 0.0242(18) 0.0265(19) 0.0214(17) -0.0028(14) 0.0069(13) -0.0012(14) N4 0.028(2) 0.028(2) 0.0251(19) -0.0060(15) 0.0055(14) -0.0022(15) N11 0.027(2) 0.029(2) 0.0256(19) 0.0023(15) 0.0080(15) 0.0012(15) N12 0.044(2) 0.033(2) 0.0229(19) 0.0015(16) 0.0052(16) -0.0079(18) N13 0.0275(19) 0.031(2) 0.0223(18) 0.0044(15) 0.0051(14) -0.0035(15) N14 0.037(2) 0.029(2) 0.0263(19) 0.0090(16) 0.0098(16) -0.0030(17) C1 0.024(2) 0.031(2) 0.032(2) -0.0052(19) 0.0063(18) -0.0009(18) C2 0.027(2) 0.041(3) 0.024(2) -0.0094(19) 0.0079(17) -0.003(2) C3 0.038(3) 0.039(3) 0.028(2) -0.005(2) 0.004(2) -0.007(2) C4 0.046(3) 0.034(3) 0.032(3) -0.008(2) 0.006(2) -0.001(2) C5 0.033(3) 0.040(3) 0.034(3) -0.020(2) 0.009(2) -0.004(2) C6 0.031(3) 0.042(3) 0.030(2) -0.007(2) 0.0055(19) -0.003(2) C7 0.031(2) 0.040(3) 0.026(2) -0.008(2) 0.0079(18) 0.002(2) C8 0.029(2) 0.027(2) 0.021(2) -0.0008(17) 0.0027(16) -0.0027(18) C9 0.023(2) 0.029(2) 0.026(2) -0.0011(18) 0.0027(16) -0.0013(17) C11 0.025(2) 0.029(2) 0.030(2) 0.0078(18) 0.0062(18) -0.0015(18) C12 0.023(2) 0.029(2) 0.032(2) 0.0055(18) 0.0074(17) 0.0023(17) C13 0.038(3) 0.032(2) 0.027(2) 0.0019(19) 0.0107(19) 0.003(2) C14 0.033(2) 0.028(2) 0.031(2) 0.0084(18) 0.0134(18) 0.0033(18) C15 0.015(2) 0.038(3) 0.023(2) 0.0081(18) 0.0037(15) -0.0010(17) C16 0.030(2) 0.035(3) 0.028(2) -0.0007(19) 0.0034(18) -0.0020(19) C17 0.031(2) 0.036(3) 0.028(2) 0.0055(19) 0.0067(18) 0.002(2) C18 0.031(2) 0.025(2) 0.027(2) -0.0010(17) 0.0094(18) -0.0004(18) C19 0.049(3) 0.033(3) 0.022(2) -0.0002(19) 0.004(2) -0.010(2) Cl1 0.073(2) 0.0302(10) 0.0278(8) -0.0002(7) 0.0070(9) 0.0023(10) O1 0.093(5) 0.056(3) 0.073(4) 0.015(3) 0.005(4) -0.008(4) O2 0.066(3) 0.062(3) 0.057(3) 0.011(3) 0.001(3) -0.008(3) O3 0.062(4) 0.055(3) 0.061(4) -0.019(3) 0.001(3) 0.006(3) O4 0.075(4) 0.071(4) 0.059(4) -0.013(3) 0.016(3) 0.021(3) O21 0.075(6) 0.055(5) 0.068(5) 0.008(5) 0.006(5) -0.007(5) O22 0.062(5) 0.052(5) 0.048(5) 0.002(5) 0.008(5) 0.001(5) O23 0.074(5) 0.064(4) 0.061(4) -0.004(4) 0.008(4) 0.000(4) O24 0.067(5) 0.056(5) 0.062(5) 0.000(5) 0.007(5) 0.001(5) Cl11 0.073(3) 0.053(3) 0.055(3) 0.007(3) 0.011(3) -0.002(3) O31 0.074(5) 0.059(5) 0.068(5) 0.002(4) 0.008(5) 0.000(5) O32 0.059(5) 0.049(5) 0.046(5) 0.006(5) 0.013(5) -0.001(5) O33 0.062(5) 0.055(4) 0.057(5) -0.004(4) 0.006(4) -0.001(4) O34 0.083(5) 0.073(5) 0.069(5) 0.003(4) 0.010(5) -0.007(5) C21 0.096(4) 0.067(4) 0.085(4) -0.015(3) 0.008(4) -0.020(3) C22 0.087(4) 0.061(3) 0.081(4) -0.019(3) 0.021(3) -0.018(3) C23 0.094(4) 0.070(3) 0.093(4) -0.020(3) 0.012(3) -0.011(3) C24 0.096(4) 0.069(4) 0.090(4) -0.018(4) 0.012(4) -0.015(4) C25 0.090(5) 0.071(4) 0.093(4) -0.025(4) 0.027(4) -0.016(4) C26 0.094(4) 0.063(4) 0.092(4) -0.017(4) 0.008(4) -0.010(4) C27 0.105(5) 0.080(5) 0.089(5) -0.019(4) 0.008(4) -0.016(4) C28 0.104(5) 0.082(4) 0.105(4) -0.016(4) -0.006(4) 0.001(4) C31 0.097(4) 0.071(4) 0.088(4) -0.017(4) 0.010(4) -0.017(4) C32 0.096(5) 0.070(5) 0.088(5) -0.018(4) 0.013(4) -0.014(4) C33 0.095(5) 0.072(5) 0.090(5) -0.020(4) 0.011(4) -0.010(4) C34 0.097(5) 0.077(4) 0.095(4) -0.018(4) 0.007(4) -0.006(4) C35 0.094(5) 0.073(4) 0.093(4) -0.019(4) 0.014(4) -0.011(4) C36 0.093(4) 0.070(4) 0.089(4) -0.018(4) 0.014(4) -0.015(4) C37 0.098(5) 0.076(5) 0.093(5) -0.017(5) 0.008(5) -0.014(5) C38 0.107(7) 0.091(7) 0.104(7) -0.010(6) 0.000(6) -0.001(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.937(4) . ? Cu1 N11 1.941(4) . ? Cu1 N2 2.025(3) 3_655 ? Cl5 C5 1.742(5) . ? Cl15 C15 1.743(4) . ? N1 C8 1.318(5) . ? N1 N2 1.394(5) . ? N2 C9 1.304(6) . ? N2 Cu1 2.025(3) 3_655 ? N3 C8 1.354(5) . ? N3 C9 1.357(5) . ? N3 N4 1.410(5) . ? N4 C1 1.270(6) . ? N11 C18 1.307(5) . ? N11 N12 1.381(5) . ? N12 C19 1.302(6) . ? N13 C18 1.355(6) . ? N13 C19 1.364(6) . ? N13 N14 1.401(5) . ? N14 C11 1.274(6) . ? C1 C2 1.472(6) . ? C1 H1A 0.9500 . ? C2 C7 1.390(6) . ? C2 C3 1.393(7) . ? C3 C4 1.386(7) . ? C3 H3A 0.9500 . ? C4 C5 1.386(7) . ? C4 H4A 0.9500 . ? C5 C6 1.385(7) . ? C6 C7 1.391(6) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C11 C12 1.467(6) . ? C11 H11A 0.9500 . ? C12 C17 1.393(6) . ? C12 C13 1.394(6) . ? C13 C14 1.384(6) . ? C13 H13A 0.9500 . ? C14 C15 1.377(6) . ? C14 H14A 0.9500 . ? C15 C16 1.384(7) . ? C16 C17 1.389(6) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? Cl1 Cl11 0.563(9) . ? Cl1 O33 1.196(18) . ? Cl1 O31 1.348(18) . ? Cl1 O4 1.429(5) . ? Cl1 O1 1.431(5) . ? Cl1 O3 1.432(5) . ? Cl1 O2 1.448(5) . ? Cl1 O23 1.454(14) . ? Cl1 O22 1.455(14) . ? Cl1 O21 1.459(14) . ? Cl1 O24 1.461(14) . ? Cl1 O32 1.601(18) . ? O1 O21 0.658(18) . ? O1 O31 0.779(19) . ? O1 Cl11 1.228(11) . ? O1 O34 1.69(2) . ? O2 O22 0.830(19) . ? O2 O32 0.91(2) . ? O2 Cl11 1.214(11) . ? O2 O33 1.811(19) . ? O3 O33 0.66(2) . ? O3 O23 0.830(17) . ? O3 Cl11 1.681(12) . ? O4 O24 0.706(16) . ? O4 O31 1.80(2) . ? O4 Cl11 1.908(11) . ? O21 Cl11 1.504(19) . ? O22 Cl11 1.209(18) . ? O23 O33 0.78(2) . ? O23 Cl11 1.430(17) . ? O23 O34 1.82(2) . ? O24 O33 1.67(3) . ? O24 Cl11 2.004(16) . ? Cl11 O34 1.452(14) . ? Cl11 O32 1.453(14) . ? Cl11 O33 1.455(14) . ? Cl11 O31 1.455(14) . ? C21 C22 1.379(17) . ? C21 C27 1.425(11) . ? C21 C26 1.488(18) . ? C22 C23 1.388(16) . ? C22 H22A 0.9500 . ? C23 C24 1.423(17) . ? C23 C28 1.427(12) . ? C24 C25 1.303(17) . ? C24 H24A 0.9500 . ? C25 C26 1.324(17) . ? C25 H25A 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C31 C32 1.3900 . ? C31 C36 1.3900 . ? C31 C37 1.427(12) . ? C32 C33 1.3900 . ? C32 H32A 0.9500 . ? C33 C34 1.3900 . ? C33 H33A 0.9500 . ? C34 C35 1.3900 . ? C34 C38 1.425(12) . ? C35 C36 1.3900 . ? C35 H35A 0.9500 . ? C36 H36A 0.9500 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 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 N1 Cu1 N11 135.06(15) . . ? N1 Cu1 N2 114.75(14) . 3_655 ? N11 Cu1 N2 109.93(15) . 3_655 ? C8 N1 N2 107.8(3) . . ? C8 N1 Cu1 130.7(3) . . ? N2 N1 Cu1 121.5(3) . . ? C9 N2 N1 106.9(3) . . ? C9 N2 Cu1 129.3(3) . 3_655 ? N1 N2 Cu1 123.2(3) . 3_655 ? C8 N3 C9 106.7(3) . . ? C8 N3 N4 132.3(3) . . ? C9 N3 N4 120.9(4) . . ? C1 N4 N3 115.9(4) . . ? C18 N11 N12 108.7(4) . . ? C18 N11 Cu1 130.1(3) . . ? N12 N11 Cu1 121.1(3) . . ? C19 N12 N11 106.1(4) . . ? C18 N13 C19 105.4(4) . . ? C18 N13 N14 133.6(4) . . ? C19 N13 N14 121.0(4) . . ? C11 N14 N13 115.8(4) . . ? N4 C1 C2 120.8(4) . . ? N4 C1 H1A 119.6 . . ? C2 C1 H1A 119.6 . . ? C7 C2 C3 119.8(4) . . ? C7 C2 C1 118.0(4) . . ? C3 C2 C1 122.2(4) . . ? C4 C3 C2 120.7(5) . . ? C4 C3 H3A 119.6 . . ? C2 C3 H3A 119.6 . . ? C5 C4 C3 118.7(5) . . ? C5 C4 H4A 120.7 . . ? C3 C4 H4A 120.7 . . ? C6 C5 C4 121.6(4) . . ? C6 C5 Cl5 119.0(4) . . ? C4 C5 Cl5 119.4(4) . . ? C5 C6 C7 119.2(5) . . ? C5 C6 H6A 120.4 . . ? C7 C6 H6A 120.4 . . ? C2 C7 C6 120.0(5) . . ? C2 C7 H7A 120.0 . . ? C6 C7 H7A 120.0 . . ? N1 C8 N3 108.7(4) . . ? N1 C8 H8A 125.6 . . ? N3 C8 H8A 125.6 . . ? N2 C9 N3 109.9(4) . . ? N2 C9 H9A 125.0 . . ? N3 C9 H9A 125.0 . . ? N14 C11 C12 119.7(4) . . ? N14 C11 H11A 120.1 . . ? C12 C11 H11A 120.1 . . ? C17 C12 C13 119.3(4) . . ? C17 C12 C11 118.7(4) . . ? C13 C12 C11 122.0(4) . . ? C14 C13 C12 120.4(4) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C15 C14 C13 119.3(4) . . ? C15 C14 H14A 120.4 . . ? C13 C14 H14A 120.4 . . ? C14 C15 C16 121.9(4) . . ? C14 C15 Cl15 119.1(4) . . ? C16 C15 Cl15 119.1(3) . . ? C15 C16 C17 118.5(4) . . ? C15 C16 H16A 120.7 . . ? C17 C16 H16A 120.7 . . ? C16 C17 C12 120.7(5) . . ? C16 C17 H17A 119.6 . . ? C12 C17 H17A 119.6 . . ? N11 C18 N13 109.0(4) . . ? N11 C18 H18A 125.5 . . ? N13 C18 H18A 125.5 . . ? N12 C19 N13 110.7(4) . . ? N12 C19 H19A 124.7 . . ? N13 C19 H19A 124.7 . . ? Cl11 Cl1 O33 105.9(16) . . ? Cl11 Cl1 O31 89.4(14) . . ? O33 Cl1 O31 137.7(11) . . ? Cl11 Cl1 O4 142.9(11) . . ? O33 Cl1 O4 105.3(10) . . ? O31 Cl1 O4 80.7(9) . . ? Cl11 Cl1 O1 58.0(11) . . ? O33 Cl1 O1 133.4(10) . . ? O31 Cl1 O1 32.4(8) . . ? O4 Cl1 O1 110.6(3) . . ? Cl11 Cl1 O3 106.5(11) . . ? O33 Cl1 O3 27.2(10) . . ? O31 Cl1 O3 111.0(10) . . ? O4 Cl1 O3 110.4(3) . . ? O1 Cl1 O3 109.8(3) . . ? Cl11 Cl1 O2 54.8(11) . . ? O33 Cl1 O2 85.9(10) . . ? O31 Cl1 O2 132.7(10) . . ? O4 Cl1 O2 108.7(3) . . ? O1 Cl1 O2 108.8(3) . . ? O3 Cl1 O2 108.5(3) . . ? Cl11 Cl1 O23 76.4(13) . . ? O33 Cl1 O23 32.5(11) . . ? O31 Cl1 O23 124.9(13) . . ? O4 Cl1 O23 137.7(7) . . ? O1 Cl1 O23 105.1(8) . . ? O3 Cl1 O23 33.4(7) . . ? O2 Cl1 O23 79.6(7) . . ? Cl11 Cl1 O22 53.5(13) . . ? O33 Cl1 O22 118.7(15) . . ? O31 Cl1 O22 102.2(15) . . ? O4 Cl1 O22 93.6(7) . . ? O1 Cl1 O22 87.9(8) . . ? O3 Cl1 O22 141.4(7) . . ? O2 Cl1 O22 33.2(7) . . ? O23 Cl1 O22 110.0(3) . . ? Cl11 Cl1 O21 83.7(14) . . ? O33 Cl1 O21 126.0(14) . . ? O31 Cl1 O21 15.4(13) . . ? O4 Cl1 O21 93.8(7) . . ? O1 Cl1 O21 26.3(7) . . ? O3 Cl1 O21 98.9(8) . . ? O2 Cl1 O21 134.8(7) . . ? O23 Cl1 O21 109.5(3) . . ? O22 Cl1 O21 109.5(3) . . ? Cl11 Cl1 O24 162.2(13) . . ? O33 Cl1 O24 77.1(11) . . ? O31 Cl1 O24 100.1(11) . . ? O4 Cl1 O24 28.3(6) . . ? O1 Cl1 O24 132.5(7) . . ? O3 Cl1 O24 84.3(7) . . ? O2 Cl1 O24 108.8(7) . . ? O23 Cl1 O24 109.4(3) . . ? O22 Cl1 O24 109.3(3) . . ? O21 Cl1 O24 109.1(3) . . ? Cl11 Cl1 O32 64.8(12) . . ? O33 Cl1 O32 115.4(9) . . ? O31 Cl1 O32 106.8(8) . . ? O4 Cl1 O32 84.0(7) . . ? O1 Cl1 O32 97.2(8) . . ? O3 Cl1 O32 141.2(8) . . ? O2 Cl1 O32 34.1(8) . . ? O23 Cl1 O32 113.7(13) . . ? O22 Cl1 O32 11.5(10) . . ? O21 Cl1 O32 116.5(13) . . ? O24 Cl1 O32 97.9(10) . . ? O21 O1 O31 30(3) . . ? O21 O1 Cl11 101.5(15) . . ? O31 O1 Cl11 90.1(15) . . ? O21 O1 Cl1 79.3(14) . . ? O31 O1 Cl1 68.0(14) . . ? Cl11 O1 Cl1 22.9(5) . . ? O21 O1 O34 138(2) . . ? O31 O1 O34 145.4(17) . . ? Cl11 O1 O34 57.0(7) . . ? Cl1 O1 O34 78.0(7) . . ? O22 O2 O32 22.0(18) . . ? O22 O2 Cl11 69.6(13) . . ? O32 O2 Cl11 85.2(14) . . ? O22 O2 Cl1 73.9(11) . . ? O32 O2 Cl1 82.2(13) . . ? Cl11 O2 Cl1 22.3(5) . . ? O22 O2 O33 114.6(14) . . ? O32 O2 O33 117.9(15) . . ? Cl11 O2 O33 53.1(7) . . ? Cl1 O2 O33 41.2(7) . . ? O33 O3 O23 62(2) . . ? O33 O3 Cl1 56.0(17) . . ? O23 O3 Cl1 74.7(11) . . ? O33 O3 Cl11 58.9(16) . . ? O23 O3 Cl11 58.2(11) . . ? Cl1 O3 Cl11 18.7(3) . . ? O24 O4 Cl1 78.4(13) . . ? O24 O4 O31 110.9(15) . . ? Cl1 O4 O31 47.7(6) . . ? O24 O4 Cl11 87.4(13) . . ? Cl1 O4 Cl11 10.2(3) . . ? O31 O4 Cl11 46.1(5) . . ? O1 O21 Cl1 74.5(14) . . ? O1 O21 Cl11 53.1(12) . . ? Cl1 O21 Cl11 21.8(4) . . ? O2 O22 Cl11 70.3(13) . . ? O2 O22 Cl1 72.9(11) . . ? Cl11 O22 Cl1 22.0(5) . . ? O33 O23 O3 48.1(19) . . ? O33 O23 Cl11 76.0(18) . . ? O3 O23 Cl11 92.2(13) . . ? O33 O23 Cl1 55.3(16) . . ? O3 O23 Cl1 71.8(11) . . ? Cl11 O23 Cl1 22.5(4) . . ? O33 O23 O34 127(2) . . ? O3 O23 O34 128.6(17) . . ? Cl11 O23 O34 51.4(8) . . ? Cl1 O23 O34 73.3(9) . . ? O4 O24 Cl1 73.3(13) . . ? O4 O24 O33 117.5(18) . . ? Cl1 O24 O33 44.3(8) . . ? O4 O24 Cl11 72.0(12) . . ? Cl1 O24 Cl11 4.9(4) . . ? O33 O24 Cl11 45.5(7) . . ? Cl1 Cl11 O22 104.5(15) . . ? Cl1 Cl11 O2 103.0(13) . . ? O22 Cl11 O2 40.1(10) . . ? Cl1 Cl11 O1 99.2(13) . . ? O22 Cl11 O1 110.5(13) . . ? O2 Cl11 O1 147.0(10) . . ? Cl1 Cl11 O23 81.2(13) . . ? O22 Cl11 O23 128.9(11) . . ? O2 Cl11 O23 88.9(9) . . ? O1 Cl11 O23 118.7(11) . . ? Cl1 Cl11 O34 154.3(13) . . ? O22 Cl11 O34 100.4(12) . . ? O2 Cl11 O34 91.8(8) . . ? O1 Cl11 O34 77.8(9) . . ? O23 Cl11 O34 78.3(9) . . ? Cl1 Cl11 O32 94.7(13) . . ? O22 Cl11 O32 10.2(12) . . ? O2 Cl11 O32 38.4(9) . . ? O1 Cl11 O32 116.0(10) . . ? O23 Cl11 O32 125.1(13) . . ? O34 Cl11 O32 109.6(3) . . ? Cl1 Cl11 O33 52.3(13) . . ? O22 Cl11 O33 117.9(15) . . ? O2 Cl11 O33 85.0(9) . . ? O1 Cl11 O33 128.1(10) . . ? O23 Cl11 O33 31.5(9) . . ? O34 Cl11 O33 109.6(3) . . ? O32 Cl11 O33 109.5(3) . . ? Cl1 Cl11 O31 67.9(13) . . ? O22 Cl11 O31 109.7(16) . . ? O2 Cl11 O31 147.3(9) . . ? O1 Cl11 O31 32.4(8) . . ? O23 Cl11 O31 118.9(13) . . ? O34 Cl11 O31 109.5(3) . . ? O32 Cl11 O31 109.3(3) . . ? O33 Cl11 O31 109.3(3) . . ? Cl1 Cl11 O21 74.5(13) . . ? O22 Cl11 O21 122.3(11) . . ? O2 Cl11 O21 161.7(11) . . ? O1 Cl11 O21 25.4(7) . . ? O23 Cl11 O21 108.3(9) . . ? O34 Cl11 O21 97.6(11) . . ? O32 Cl11 O21 123.3(13) . . ? O33 Cl11 O21 106.4(14) . . ? O31 Cl11 O21 15.1(12) . . ? Cl1 Cl11 O3 54.7(10) . . ? O22 Cl11 O3 140.5(13) . . ? O2 Cl11 O3 106.6(7) . . ? O1 Cl11 O3 106.2(7) . . ? O23 Cl11 O3 29.6(7) . . ? O34 Cl11 O3 101.2(8) . . ? O32 Cl11 O3 131.7(8) . . ? O33 Cl11 O3 22.8(8) . . ? O31 Cl11 O3 93.6(9) . . ? O21 Cl11 O3 87.0(9) . . ? Cl1 Cl11 O4 26.8(9) . . ? O22 Cl11 O4 81.5(10) . . ? O2 Cl11 O4 94.3(6) . . ? O1 Cl11 O4 94.6(6) . . ? O23 Cl11 O4 106.4(8) . . ? O34 Cl11 O4 172.3(8) . . ? O32 Cl11 O4 73.0(8) . . ? O33 Cl11 O4 75.6(8) . . ? O31 Cl11 O4 63.0(8) . . ? O21 Cl11 O4 75.3(8) . . ? O3 Cl11 O4 81.5(5) . . ? O1 O31 Cl1 79.6(14) . . ? O1 O31 Cl11 57.6(12) . . ? Cl1 O31 Cl11 22.8(5) . . ? O1 O31 O4 126.9(19) . . ? Cl1 O31 O4 51.6(7) . . ? Cl11 O31 O4 70.9(8) . . ? O2 O32 Cl11 56.3(10) . . ? O2 O32 Cl1 63.7(11) . . ? Cl11 O32 Cl1 20.5(4) . . ? O3 O33 O23 70(2) . . ? O3 O33 Cl1 97(2) . . ? O23 O33 Cl1 92(2) . . ? O3 O33 Cl11 98.3(19) . . ? O23 O33 Cl11 72.5(18) . . ? Cl1 O33 Cl11 21.9(5) . . ? O3 O33 O24 104(2) . . ? O23 O33 O24 150(2) . . ? Cl1 O33 O24 58.6(9) . . ? Cl11 O33 O24 79.5(10) . . ? O3 O33 O2 137(2) . . ? O23 O33 O2 81(2) . . ? Cl1 O33 O2 52.9(7) . . ? Cl11 O33 O2 41.9(6) . . ? O24 O33 O2 85.5(10) . . ? Cl11 O34 O1 45.2(6) . . ? Cl11 O34 O23 50.3(7) . . ? O1 O34 O23 81.3(10) . . ? Cl11 O34 Cl1 7.1(4) . . ? O1 O34 Cl1 45.1(5) . . ? O23 O34 Cl1 44.8(7) . . ? C22 C21 C27 121.4(13) . . ? C22 C21 C26 114.6(12) . . ? C27 C21 C26 123.8(13) . . ? C21 C22 C23 124.0(13) . . ? C21 C22 H22A 118.0 . . ? C23 C22 H22A 118.0 . . ? C22 C23 C24 115.3(12) . . ? C22 C23 C28 118.6(12) . . ? C24 C23 C28 126.1(13) . . ? C25 C24 C23 123.8(13) . . ? C25 C24 H24A 118.1 . . ? C23 C24 H24A 118.1 . . ? C24 C25 C26 121.2(13) . . ? C24 C25 H25A 119.4 . . ? C26 C25 H25A 119.4 . . ? C25 C26 C21 121.0(13) . . ? C25 C26 H26 119.5 . . ? C21 C26 H26 119.5 . . ? C21 C27 H27A 109.5 . . ? C21 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C21 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C23 C28 H28A 109.5 . . ? C23 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C23 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C32 C31 C36 120.0 . . ? C32 C31 C37 137(2) . . ? C36 C31 C37 103(2) . . ? C31 C32 C33 120.0 . . ? C31 C32 H32A 120.0 . . ? C33 C32 H32A 120.0 . . ? C34 C33 C32 120.0 . . ? C34 C33 H33A 120.0 . . ? C32 C33 H33A 120.0 . . ? C33 C34 C35 120.0 . . ? C33 C34 C38 104(2) . . ? C35 C34 C38 135(2) . . ? C34 C35 C36 120.0 . . ? C34 C35 H35A 120.0 . . ? C36 C35 H35A 120.0 . . ? C35 C36 C31 120.0 . . ? C35 C36 H36A 120.0 . . ? C31 C36 H36A 120.0 . . ? C31 C37 H37A 109.5 . . ? C31 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C31 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C34 C38 H38A 109.5 . . ? C34 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C34 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 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 C8 N1 N2 C9 0.5(5) . . . . ? Cu1 N1 N2 C9 179.1(3) . . . . ? C8 N1 N2 Cu1 172.1(3) . . . 3_655 ? Cu1 N1 N2 Cu1 -9.4(4) . . . 3_655 ? C8 N3 N4 C1 5.9(7) . . . . ? C9 N3 N4 C1 -174.0(4) . . . . ? C18 N11 N12 C19 0.6(5) . . . . ? Cu1 N11 N12 C19 -176.9(3) . . . . ? C18 N13 N14 C11 2.6(7) . . . . ? C19 N13 N14 C11 -179.9(4) . . . . ? N3 N4 C1 C2 179.1(4) . . . . ? N4 C1 C2 C7 179.7(4) . . . . ? N4 C1 C2 C3 0.3(7) . . . . ? C7 C2 C3 C4 -0.4(7) . . . . ? C1 C2 C3 C4 179.0(5) . . . . ? C2 C3 C4 C5 0.9(7) . . . . ? C3 C4 C5 C6 -0.9(8) . . . . ? C3 C4 C5 Cl5 178.2(4) . . . . ? C4 C5 C6 C7 0.5(7) . . . . ? Cl5 C5 C6 C7 -178.6(4) . . . . ? C3 C2 C7 C6 0.0(7) . . . . ? C1 C2 C7 C6 -179.5(4) . . . . ? C5 C6 C7 C2 -0.1(7) . . . . ? N2 N1 C8 N3 -0.8(5) . . . . ? Cu1 N1 C8 N3 -179.2(3) . . . . ? C9 N3 C8 N1 0.8(5) . . . . ? N4 N3 C8 N1 -179.1(4) . . . . ? N1 N2 C9 N3 0.0(5) . . . . ? Cu1 N2 C9 N3 -170.9(3) 3_655 . . . ? C8 N3 C9 N2 -0.5(5) . . . . ? N4 N3 C9 N2 179.4(3) . . . . ? N13 N14 C11 C12 -179.8(4) . . . . ? N14 C11 C12 C17 179.7(4) . . . . ? N14 C11 C12 C13 -0.9(7) . . . . ? C17 C12 C13 C14 -0.4(7) . . . . ? C11 C12 C13 C14 -179.8(4) . . . . ? C12 C13 C14 C15 0.1(7) . . . . ? C13 C14 C15 C16 0.0(7) . . . . ? C13 C14 C15 Cl15 -179.9(4) . . . . ? C14 C15 C16 C17 0.2(7) . . . . ? Cl15 C15 C16 C17 -179.8(3) . . . . ? C15 C16 C17 C12 -0.6(7) . . . . ? C13 C12 C17 C16 0.7(7) . . . . ? C11 C12 C17 C16 -179.9(4) . . . . ? N12 N11 C18 N13 -0.7(5) . . . . ? Cu1 N11 C18 N13 176.5(3) . . . . ? C19 N13 C18 N11 0.5(5) . . . . ? N14 N13 C18 N11 178.3(4) . . . . ? N11 N12 C19 N13 -0.3(6) . . . . ? C18 N13 C19 N12 -0.1(6) . . . . ? N14 N13 C19 N12 -178.3(4) . . . . ? Cl11 Cl1 O1 O21 -167(2) . . . . ? O33 Cl1 O1 O21 -85(3) . . . . ? O31 Cl1 O1 O21 29(3) . . . . ? O4 Cl1 O1 O21 53.1(19) . . . . ? O3 Cl1 O1 O21 -69.0(18) . . . . ? O2 Cl1 O1 O21 172.4(18) . . . . ? O23 Cl1 O1 O21 -103.7(16) . . . . ? O22 Cl1 O1 O21 146.2(16) . . . . ? O24 Cl1 O1 O21 32(2) . . . . ? O32 Cl1 O1 O21 139(2) . . . . ? Cl11 Cl1 O1 O31 164(3) . . . . ? O33 Cl1 O1 O31 -114.2(18) . . . . ? O4 Cl1 O1 O31 24(2) . . . . ? O3 Cl1 O1 O31 -98(2) . . . . ? O2 Cl1 O1 O31 143.2(19) . . . . ? O23 Cl1 O1 O31 -133(2) . . . . ? O22 Cl1 O1 O31 117(2) . . . . ? O21 Cl1 O1 O31 -29(3) . . . . ? O24 Cl1 O1 O31 3(2) . . . . ? O32 Cl1 O1 O31 110.2(16) . . . . ? O33 Cl1 O1 Cl11 81.5(19) . . . . ? O31 Cl1 O1 Cl11 -164(3) . . . . ? O4 Cl1 O1 Cl11 -140.4(13) . . . . ? O3 Cl1 O1 Cl11 97.6(13) . . . . ? O2 Cl1 O1 Cl11 -21.1(13) . . . . ? O23 Cl1 O1 Cl11 62.8(15) . . . . ? O22 Cl1 O1 Cl11 -47.3(15) . . . . ? O21 Cl1 O1 Cl11 167(2) . . . . ? O24 Cl1 O1 Cl11 -161.7(16) . . . . ? O32 Cl1 O1 Cl11 -54.1(14) . . . . ? Cl11 Cl1 O1 O34 -22.0(12) . . . . ? O33 Cl1 O1 O34 59.5(13) . . . . ? O31 Cl1 O1 O34 174(2) . . . . ? O4 Cl1 O1 O34 -162.4(7) . . . . ? O3 Cl1 O1 O34 75.5(8) . . . . ? O2 Cl1 O1 O34 -43.1(8) . . . . ? O23 Cl1 O1 O34 40.8(11) . . . . ? O22 Cl1 O1 O34 -69.3(10) . . . . ? O21 Cl1 O1 O34 144(2) . . . . ? O24 Cl1 O1 O34 176.2(11) . . . . ? O32 Cl1 O1 O34 -76.1(7) . . . . ? Cl11 Cl1 O2 O22 -75.6(19) . . . . ? O33 Cl1 O2 O22 171.7(16) . . . . ? O31 Cl1 O2 O22 -27.7(18) . . . . ? O4 Cl1 O2 O22 66.9(13) . . . . ? O1 Cl1 O2 O22 -53.6(13) . . . . ? O3 Cl1 O2 O22 -173.1(13) . . . . ? O23 Cl1 O2 O22 -156.1(13) . . . . ? O21 Cl1 O2 O22 -48.9(17) . . . . ? O24 Cl1 O2 O22 96.7(11) . . . . ? O32 Cl1 O2 O22 20.9(18) . . . . ? Cl11 Cl1 O2 O32 -96.4(19) . . . . ? O33 Cl1 O2 O32 150.8(14) . . . . ? O31 Cl1 O2 O32 -48.6(16) . . . . ? O4 Cl1 O2 O32 46.0(13) . . . . ? O1 Cl1 O2 O32 -74.5(13) . . . . ? O3 Cl1 O2 O32 166.0(12) . . . . ? O23 Cl1 O2 O32 -177.0(15) . . . . ? O22 Cl1 O2 O32 -20.9(18) . . . . ? O21 Cl1 O2 O32 -69.7(18) . . . . ? O24 Cl1 O2 O32 75.9(14) . . . . ? O33 Cl1 O2 Cl11 -112.8(18) . . . . ? O31 Cl1 O2 Cl11 47.8(14) . . . . ? O4 Cl1 O2 Cl11 142.4(14) . . . . ? O1 Cl1 O2 Cl11 21.9(14) . . . . ? O3 Cl1 O2 Cl11 -97.5(14) . . . . ? O23 Cl1 O2 Cl11 -80.6(15) . . . . ? O22 Cl1 O2 Cl11 75.6(19) . . . . ? O21 Cl1 O2 Cl11 26.7(17) . . . . ? O24 Cl1 O2 Cl11 172.3(15) . . . . ? O32 Cl1 O2 Cl11 96.4(19) . . . . ? Cl11 Cl1 O2 O33 112.8(18) . . . . ? O31 Cl1 O2 O33 160.6(16) . . . . ? O4 Cl1 O2 O33 -104.8(10) . . . . ? O1 Cl1 O2 O33 134.7(10) . . . . ? O3 Cl1 O2 O33 15.2(10) . . . . ? O23 Cl1 O2 O33 32.2(11) . . . . ? O22 Cl1 O2 O33 -171.7(16) . . . . ? O21 Cl1 O2 O33 139.5(14) . . . . ? O24 Cl1 O2 O33 -74.9(11) . . . . ? O32 Cl1 O2 O33 -150.8(14) . . . . ? Cl11 Cl1 O3 O33 -93(3) . . . . ? O31 Cl1 O3 O33 172(2) . . . . ? O4 Cl1 O3 O33 84(2) . . . . ? O1 Cl1 O3 O33 -154(2) . . . . ? O2 Cl1 O3 O33 -35(2) . . . . ? O23 Cl1 O3 O33 -66(2) . . . . ? O22 Cl1 O3 O33 -41(3) . . . . ? O21 Cl1 O3 O33 -179(2) . . . . ? O24 Cl1 O3 O33 73(2) . . . . ? O32 Cl1 O3 O33 -23(3) . . . . ? Cl11 Cl1 O3 O23 -26.2(18) . . . . ? O33 Cl1 O3 O23 66(2) . . . . ? O31 Cl1 O3 O23 -122.1(16) . . . . ? O4 Cl1 O3 O23 150.4(14) . . . . ? O1 Cl1 O3 O23 -87.5(14) . . . . ? O2 Cl1 O3 O23 31.4(14) . . . . ? O22 Cl1 O3 O23 25(2) . . . . ? O21 Cl1 O3 O23 -112.2(12) . . . . ? O24 Cl1 O3 O23 139.3(13) . . . . ? O32 Cl1 O3 O23 43.8(18) . . . . ? O33 Cl1 O3 Cl11 93(3) . . . . ? O31 Cl1 O3 Cl11 -95.8(15) . . . . ? O4 Cl1 O3 Cl11 176.6(12) . . . . ? O1 Cl1 O3 Cl11 -61.2(12) . . . . ? O2 Cl1 O3 Cl11 57.6(12) . . . . ? O23 Cl1 O3 Cl11 26.2(18) . . . . ? O22 Cl1 O3 Cl11 51.6(16) . . . . ? O21 Cl1 O3 Cl11 -86.0(14) . . . . ? O24 Cl1 O3 Cl11 165.5(14) . . . . ? O32 Cl1 O3 Cl11 70.1(14) . . . . ? Cl11 Cl1 O4 O24 151(2) . . . . ? O33 Cl1 O4 O24 4(2) . . . . ? O31 Cl1 O4 O24 -133(2) . . . . ? O1 Cl1 O4 O24 -145.5(15) . . . . ? O3 Cl1 O4 O24 -23.8(16) . . . . ? O2 Cl1 O4 O24 95.1(16) . . . . ? O23 Cl1 O4 O24 0(2) . . . . ? O22 Cl1 O4 O24 125.4(14) . . . . ? O21 Cl1 O4 O24 -124.7(14) . . . . ? O32 Cl1 O4 O24 119.0(18) . . . . ? Cl11 Cl1 O4 O31 -76(2) . . . . ? O33 Cl1 O4 O31 137.1(10) . . . . ? O1 Cl1 O4 O31 -12.7(11) . . . . ? O3 Cl1 O4 O31 109.0(10) . . . . ? O2 Cl1 O4 O31 -132.1(10) . . . . ? O23 Cl1 O4 O31 132.9(17) . . . . ? O22 Cl1 O4 O31 -101.8(15) . . . . ? O21 Cl1 O4 O31 8.1(15) . . . . ? O24 Cl1 O4 O31 133(2) . . . . ? O32 Cl1 O4 O31 -108.2(9) . . . . ? O33 Cl1 O4 Cl11 -146(2) . . . . ? O31 Cl1 O4 Cl11 76(2) . . . . ? O1 Cl1 O4 Cl11 63.7(19) . . . . ? O3 Cl1 O4 Cl11 -175(2) . . . . ? O2 Cl1 O4 Cl11 -55.7(19) . . . . ? O23 Cl1 O4 Cl11 -151(2) . . . . ? O22 Cl1 O4 Cl11 -25(2) . . . . ? O21 Cl1 O4 Cl11 85(2) . . . . ? O24 Cl1 O4 Cl11 -151(2) . . . . ? O32 Cl1 O4 Cl11 -31.8(17) . . . . ? O31 O1 O21 Cl1 64(4) . . . . ? Cl11 O1 O21 Cl1 -5.3(9) . . . . ? O34 O1 O21 Cl1 -58(2) . . . . ? O31 O1 O21 Cl11 70(5) . . . . ? Cl1 O1 O21 Cl11 5.3(9) . . . . ? O34 O1 O21 Cl11 -52.8(17) . . . . ? Cl11 Cl1 O21 O1 11(2) . . . . ? O33 Cl1 O21 O1 116(2) . . . . ? O31 Cl1 O21 O1 -100(6) . . . . ? O4 Cl1 O21 O1 -131.4(16) . . . . ? O3 Cl1 O21 O1 117.3(16) . . . . ? O2 Cl1 O21 O1 -10(2) . . . . ? O23 Cl1 O21 O1 84.5(18) . . . . ? O22 Cl1 O21 O1 -36.2(18) . . . . ? O24 Cl1 O21 O1 -155.7(17) . . . . ? O32 Cl1 O21 O1 -46(2) . . . . ? O33 Cl1 O21 Cl11 105.0(18) . . . . ? O31 Cl1 O21 Cl11 -111(5) . . . . ? O4 Cl1 O21 Cl11 -142.9(12) . . . . ? O1 Cl1 O21 Cl11 -11(2) . . . . ? O3 Cl1 O21 Cl11 105.8(11) . . . . ? O2 Cl1 O21 Cl11 -21.7(13) . . . . ? O23 Cl1 O21 Cl11 73.1(13) . . . . ? O22 Cl1 O21 Cl11 -47.6(13) . . . . ? O24 Cl1 O21 Cl11 -167.2(13) . . . . ? O32 Cl1 O21 Cl11 -57.7(12) . . . . ? O32 O2 O22 Cl11 133(5) . . . . ? Cl1 O2 O22 Cl11 23.0(5) . . . . ? O33 O2 O22 Cl11 29.1(12) . . . . ? O32 O2 O22 Cl1 110(5) . . . . ? Cl11 O2 O22 Cl1 -23.0(5) . . . . ? O33 O2 O22 Cl1 6.0(11) . . . . ? Cl11 Cl1 O22 O2 79.5(19) . . . . ? O33 Cl1 O22 O2 -9.5(18) . . . . ? O31 Cl1 O22 O2 159.5(13) . . . . ? O4 Cl1 O22 O2 -119.2(11) . . . . ? O1 Cl1 O22 O2 130.3(11) . . . . ? O3 Cl1 O22 O2 10.5(19) . . . . ? O23 Cl1 O22 O2 25.0(14) . . . . ? O21 Cl1 O22 O2 145.5(13) . . . . ? O24 Cl1 O22 O2 -95.1(13) . . . . ? O32 Cl1 O22 O2 -86(7) . . . . ? O33 Cl1 O22 Cl11 -89(2) . . . . ? O31 Cl1 O22 Cl11 80.0(18) . . . . ? O4 Cl1 O22 Cl11 161.3(16) . . . . ? O1 Cl1 O22 Cl11 50.7(16) . . . . ? O3 Cl1 O22 Cl11 -69(2) . . . . ? O2 Cl1 O22 Cl11 -79.5(19) . . . . ? O23 Cl1 O22 Cl11 -54.5(17) . . . . ? O21 Cl1 O22 Cl11 65.9(17) . . . . ? O24 Cl1 O22 Cl11 -174.6(17) . . . . ? O32 Cl1 O22 Cl11 -165(8) . . . . ? Cl1 O3 O23 O33 -59.3(19) . . . . ? Cl11 O3 O23 O33 -69(2) . . . . ? O33 O3 O23 Cl11 69(2) . . . . ? Cl1 O3 O23 Cl11 9.6(6) . . . . ? O33 O3 O23 Cl1 59.3(19) . . . . ? Cl11 O3 O23 Cl1 -9.6(6) . . . . ? O33 O3 O23 O34 109(3) . . . . ? Cl1 O3 O23 O34 49.5(19) . . . . ? Cl11 O3 O23 O34 39.9(15) . . . . ? Cl11 Cl1 O23 O33 -155(3) . . . . ? O31 Cl1 O23 O33 126(2) . . . . ? O4 Cl1 O23 O33 8(3) . . . . ? O1 Cl1 O23 O33 154(2) . . . . ? O3 Cl1 O23 O33 51(2) . . . . ? O2 Cl1 O23 O33 -99(3) . . . . ? O22 Cl1 O23 O33 -112(3) . . . . ? O21 Cl1 O23 O33 127(3) . . . . ? O24 Cl1 O23 O33 8(3) . . . . ? O32 Cl1 O23 O33 -101(2) . . . . ? Cl11 Cl1 O23 O3 154.1(18) . . . . ? O33 Cl1 O23 O3 -51(2) . . . . ? O31 Cl1 O23 O3 74.7(17) . . . . ? O4 Cl1 O23 O3 -43.5(19) . . . . ? O1 Cl1 O23 O3 103.2(11) . . . . ? O2 Cl1 O23 O3 -149.9(13) . . . . ? O22 Cl1 O23 O3 -163.5(14) . . . . ? O21 Cl1 O23 O3 76.1(14) . . . . ? O24 Cl1 O23 O3 -43.5(14) . . . . ? O32 Cl1 O23 O3 -151.7(11) . . . . ? O33 Cl1 O23 Cl11 155(3) . . . . ? O31 Cl1 O23 Cl11 -79.5(16) . . . . ? O4 Cl1 O23 Cl11 162.3(14) . . . . ? O1 Cl1 O23 Cl11 -50.9(12) . . . . ? O3 Cl1 O23 Cl11 -154.1(18) . . . . ? O2 Cl1 O23 Cl11 56.0(11) . . . . ? O22 Cl1 O23 Cl11 42.4(14) . . . . ? O21 Cl1 O23 Cl11 -78.1(14) . . . . ? O24 Cl1 O23 Cl11 162.4(14) . . . . ? O32 Cl1 O23 Cl11 54.2(12) . . . . ? Cl11 Cl1 O23 O34 12.6(10) . . . . ? O33 Cl1 O23 O34 167(3) . . . . ? O31 Cl1 O23 O34 -66.9(14) . . . . ? O4 Cl1 O23 O34 174.9(8) . . . . ? O1 Cl1 O23 O34 -38.3(9) . . . . ? O3 Cl1 O23 O34 -141.6(17) . . . . ? O2 Cl1 O23 O34 68.5(8) . . . . ? O22 Cl1 O23 O34 54.9(11) . . . . ? O21 Cl1 O23 O34 -65.5(11) . . . . ? O24 Cl1 O23 O34 174.9(11) . . . . ? O32 Cl1 O23 O34 66.7(10) . . . . ? O31 O4 O24 Cl1 -35.5(11) . . . . ? Cl11 O4 O24 Cl1 5.0(4) . . . . ? Cl1 O4 O24 O33 -3.4(16) . . . . ? O31 O4 O24 O33 -39(2) . . . . ? Cl11 O4 O24 O33 1.6(17) . . . . ? Cl1 O4 O24 Cl11 -5.0(4) . . . . ? O31 O4 O24 Cl11 -40.5(9) . . . . ? Cl11 Cl1 O24 O4 -74(5) . . . . ? O33 Cl1 O24 O4 -176(2) . . . . ? O31 Cl1 O24 O4 47.3(19) . . . . ? O1 Cl1 O24 O4 46.0(18) . . . . ? O3 Cl1 O24 O4 157.7(15) . . . . ? O2 Cl1 O24 O4 -94.7(14) . . . . ? O23 Cl1 O24 O4 -179.9(15) . . . . ? O22 Cl1 O24 O4 -59.5(16) . . . . ? O21 Cl1 O24 O4 60.2(16) . . . . ? O32 Cl1 O24 O4 -61.4(17) . . . . ? Cl11 Cl1 O24 O33 102(4) . . . . ? O31 Cl1 O24 O33 -136.9(11) . . . . ? O4 Cl1 O24 O33 176(2) . . . . ? O1 Cl1 O24 O33 -138.3(12) . . . . ? O3 Cl1 O24 O33 -26.6(10) . . . . ? O2 Cl1 O24 O33 81.1(11) . . . . ? O23 Cl1 O24 O33 -4.2(15) . . . . ? O22 Cl1 O24 O33 116.2(15) . . . . ? O21 Cl1 O24 O33 -124.0(15) . . . . ? O32 Cl1 O24 O33 114.4(10) . . . . ? O33 Cl1 O24 Cl11 -102(4) . . . . ? O31 Cl1 O24 Cl11 121(5) . . . . ? O4 Cl1 O24 Cl11 74(5) . . . . ? O1 Cl1 O24 Cl11 120(4) . . . . ? O3 Cl1 O24 Cl11 -129(4) . . . . ? O2 Cl1 O24 Cl11 -21(4) . . . . ? O23 Cl1 O24 Cl11 -106(4) . . . . ? O22 Cl1 O24 Cl11 14(4) . . . . ? O21 Cl1 O24 Cl11 134(4) . . . . ? O32 Cl1 O24 Cl11 12(4) . . . . ? O33 Cl1 Cl11 O22 114.2(18) . . . . ? O31 Cl1 Cl11 O22 -105.7(18) . . . . ? O4 Cl1 Cl11 O22 -32(3) . . . . ? O1 Cl1 Cl11 O22 -114.1(17) . . . . ? O3 Cl1 Cl11 O22 142.5(12) . . . . ? O2 Cl1 Cl11 O22 41.3(11) . . . . ? O23 Cl1 Cl11 O22 128.0(13) . . . . ? O21 Cl1 Cl11 O22 -120.0(12) . . . . ? O24 Cl1 Cl11 O22 17(5) . . . . ? O32 Cl1 Cl11 O22 3.2(17) . . . . ? O33 Cl1 Cl11 O2 73.0(15) . . . . ? O31 Cl1 Cl11 O2 -147.0(10) . . . . ? O4 Cl1 Cl11 O2 -73.4(19) . . . . ? O1 Cl1 Cl11 O2 -155.4(15) . . . . ? O3 Cl1 Cl11 O2 101.3(8) . . . . ? O23 Cl1 Cl11 O2 86.8(11) . . . . ? O22 Cl1 Cl11 O2 -41.3(11) . . . . ? O21 Cl1 Cl11 O2 -161.3(11) . . . . ? O24 Cl1 Cl11 O2 -24(5) . . . . ? O32 Cl1 Cl11 O2 -38.0(10) . . . . ? O33 Cl1 Cl11 O1 -131.7(12) . . . . ? O31 Cl1 Cl11 O1 8.4(15) . . . . ? O4 Cl1 Cl11 O1 82.0(18) . . . . ? O3 Cl1 Cl11 O1 -103.4(8) . . . . ? O2 Cl1 Cl11 O1 155.4(15) . . . . ? O23 Cl1 Cl11 O1 -117.9(12) . . . . ? O22 Cl1 Cl11 O1 114.1(17) . . . . ? O21 Cl1 Cl11 O1 -6.0(10) . . . . ? O24 Cl1 Cl11 O1 131(4) . . . . ? O32 Cl1 Cl11 O1 117.3(12) . . . . ? O33 Cl1 Cl11 O23 -13.8(16) . . . . ? O31 Cl1 Cl11 O23 126.2(14) . . . . ? O4 Cl1 Cl11 O23 -160.2(16) . . . . ? O1 Cl1 Cl11 O23 117.9(12) . . . . ? O3 Cl1 Cl11 O23 14.5(10) . . . . ? O2 Cl1 Cl11 O23 -86.8(11) . . . . ? O22 Cl1 Cl11 O23 -128.0(13) . . . . ? O21 Cl1 Cl11 O23 111.9(5) . . . . ? O24 Cl1 Cl11 O23 -111(4) . . . . ? O32 Cl1 Cl11 O23 -124.8(13) . . . . ? O33 Cl1 Cl11 O34 -51(3) . . . . ? O31 Cl1 Cl11 O34 89(3) . . . . ? O4 Cl1 Cl11 O34 162.8(19) . . . . ? O1 Cl1 Cl11 O34 81(3) . . . . ? O3 Cl1 Cl11 O34 -22(3) . . . . ? O2 Cl1 Cl11 O34 -124(3) . . . . ? O23 Cl1 Cl11 O34 -37(3) . . . . ? O22 Cl1 Cl11 O34 -165(4) . . . . ? O21 Cl1 Cl11 O34 75(3) . . . . ? O24 Cl1 Cl11 O34 -148(3) . . . . ? O32 Cl1 Cl11 O34 -162(3) . . . . ? O33 Cl1 Cl11 O32 111.0(10) . . . . ? O31 Cl1 Cl11 O32 -109.0(6) . . . . ? O4 Cl1 Cl11 O32 -35.4(18) . . . . ? O1 Cl1 Cl11 O32 -117.3(12) . . . . ? O3 Cl1 Cl11 O32 139.3(9) . . . . ? O2 Cl1 Cl11 O32 38.0(10) . . . . ? O23 Cl1 Cl11 O32 124.8(13) . . . . ? O22 Cl1 Cl11 O32 -3.2(17) . . . . ? O21 Cl1 Cl11 O32 -123.3(13) . . . . ? O24 Cl1 Cl11 O32 14(4) . . . . ? O31 Cl1 Cl11 O33 140.0(14) . . . . ? O4 Cl1 Cl11 O33 -146(2) . . . . ? O1 Cl1 Cl11 O33 131.7(12) . . . . ? O3 Cl1 Cl11 O33 28.3(10) . . . . ? O2 Cl1 Cl11 O33 -73.0(15) . . . . ? O23 Cl1 Cl11 O33 13.8(16) . . . . ? O22 Cl1 Cl11 O33 -114.2(18) . . . . ? O21 Cl1 Cl11 O33 125.7(15) . . . . ? O24 Cl1 Cl11 O33 -97(4) . . . . ? O32 Cl1 Cl11 O33 -111.0(10) . . . . ? O33 Cl1 Cl11 O31 -140.0(14) . . . . ? O4 Cl1 Cl11 O31 73.6(17) . . . . ? O1 Cl1 Cl11 O31 -8.4(15) . . . . ? O3 Cl1 Cl11 O31 -111.7(11) . . . . ? O2 Cl1 Cl11 O31 147.0(10) . . . . ? O23 Cl1 Cl11 O31 -126.2(14) . . . . ? O22 Cl1 Cl11 O31 105.7(18) . . . . ? O21 Cl1 Cl11 O31 -14.3(15) . . . . ? O24 Cl1 Cl11 O31 123(4) . . . . ? O32 Cl1 Cl11 O31 109.0(6) . . . . ? O33 Cl1 Cl11 O21 -125.7(15) . . . . ? O31 Cl1 Cl11 O21 14.3(15) . . . . ? O4 Cl1 Cl11 O21 87.9(18) . . . . ? O1 Cl1 Cl11 O21 6.0(10) . . . . ? O3 Cl1 Cl11 O21 -97.4(9) . . . . ? O2 Cl1 Cl11 O21 161.3(11) . . . . ? O23 Cl1 Cl11 O21 -111.9(5) . . . . ? O22 Cl1 Cl11 O21 120.0(12) . . . . ? O24 Cl1 Cl11 O21 137(4) . . . . ? O32 Cl1 Cl11 O21 123.3(13) . . . . ? O33 Cl1 Cl11 O3 -28.3(10) . . . . ? O31 Cl1 Cl11 O3 111.7(11) . . . . ? O4 Cl1 Cl11 O3 -174.7(19) . . . . ? O1 Cl1 Cl11 O3 103.4(7) . . . . ? O2 Cl1 Cl11 O3 -101.3(8) . . . . ? O23 Cl1 Cl11 O3 -14.5(10) . . . . ? O22 Cl1 Cl11 O3 -142.5(12) . . . . ? O21 Cl1 Cl11 O3 97.4(9) . . . . ? O24 Cl1 Cl11 O3 -126(4) . . . . ? O32 Cl1 Cl11 O3 -139.3(9) . . . . ? O33 Cl1 Cl11 O4 146(2) . . . . ? O31 Cl1 Cl11 O4 -73.6(17) . . . . ? O1 Cl1 Cl11 O4 -82.0(18) . . . . ? O3 Cl1 Cl11 O4 174.7(19) . . . . ? O2 Cl1 Cl11 O4 73.4(19) . . . . ? O23 Cl1 Cl11 O4 160.2(16) . . . . ? O22 Cl1 Cl11 O4 32(3) . . . . ? O21 Cl1 Cl11 O4 -87.9(18) . . . . ? O24 Cl1 Cl11 O4 49(4) . . . . ? O32 Cl1 Cl11 O4 35.4(18) . . . . ? O2 O22 Cl11 Cl1 -93.1(17) . . . . ? Cl1 O22 Cl11 O2 93.1(17) . . . . ? O2 O22 Cl11 O1 161.1(12) . . . . ? Cl1 O22 Cl11 O1 -105.8(18) . . . . ? O2 O22 Cl11 O23 -2.9(18) . . . . ? Cl1 O22 Cl11 O23 90.2(19) . . . . ? O2 O22 Cl11 O34 80.4(13) . . . . ? Cl1 O22 Cl11 O34 173.5(17) . . . . ? O2 O22 Cl11 O32 -75(9) . . . . ? Cl1 O22 Cl11 O32 18(10) . . . . ? O2 O22 Cl11 O33 -38.4(17) . . . . ? Cl1 O22 Cl11 O33 54.7(15) . . . . ? O2 O22 Cl11 O31 -164.4(11) . . . . ? Cl1 O22 Cl11 O31 -71.3(15) . . . . ? O2 O22 Cl11 O21 -173.7(14) . . . . ? Cl1 O22 Cl11 O21 -80.6(17) . . . . ? O2 O22 Cl11 O3 -42(2) . . . . ? Cl1 O22 Cl11 O3 51.3(13) . . . . ? O2 O22 Cl11 O4 -107.1(11) . . . . ? Cl1 O22 Cl11 O4 -14.0(12) . . . . ? O22 O2 Cl11 Cl1 97.1(18) . . . . ? O32 O2 Cl11 Cl1 81.1(18) . . . . ? O33 O2 Cl11 Cl1 -49.4(15) . . . . ? O32 O2 Cl11 O22 -16.0(19) . . . . ? Cl1 O2 Cl11 O22 -97.1(18) . . . . ? O33 O2 Cl11 O22 -146.5(15) . . . . ? O22 O2 Cl11 O1 -34(2) . . . . ? O32 O2 Cl11 O1 -50(2) . . . . ? Cl1 O2 Cl11 O1 -131(3) . . . . ? O33 O2 Cl11 O1 179.6(18) . . . . ? O22 O2 Cl11 O23 177.8(14) . . . . ? O32 O2 Cl11 O23 161.8(13) . . . . ? Cl1 O2 Cl11 O23 80.7(14) . . . . ? O33 O2 Cl11 O23 31.3(9) . . . . ? O22 O2 Cl11 O34 -104.0(15) . . . . ? O32 O2 Cl11 O34 -120.0(11) . . . . ? Cl1 O2 Cl11 O34 158.9(15) . . . . ? O33 O2 Cl11 O34 109.5(3) . . . . ? O22 O2 Cl11 O32 16.0(19) . . . . ? Cl1 O2 Cl11 O32 -81.1(19) . . . . ? O33 O2 Cl11 O32 -130.5(12) . . . . ? O22 O2 Cl11 O33 146.5(15) . . . . ? O32 O2 Cl11 O33 130.5(12) . . . . ? Cl1 O2 Cl11 O33 49.4(15) . . . . ? O22 O2 Cl11 O31 28(2) . . . . ? O32 O2 Cl11 O31 12(2) . . . . ? Cl1 O2 Cl11 O31 -69.1(19) . . . . ? O33 O2 Cl11 O31 -118.5(14) . . . . ? O22 O2 Cl11 O21 17(4) . . . . ? O32 O2 Cl11 O21 1(4) . . . . ? Cl1 O2 Cl11 O21 -80(4) . . . . ? O33 O2 Cl11 O21 -129(4) . . . . ? O22 O2 Cl11 O3 153.8(14) . . . . ? O32 O2 Cl11 O3 137.8(12) . . . . ? Cl1 O2 Cl11 O3 56.7(11) . . . . ? O33 O2 Cl11 O3 7.3(9) . . . . ? O22 O2 Cl11 O4 71.4(13) . . . . ? O32 O2 Cl11 O4 55.4(14) . . . . ? Cl1 O2 Cl11 O4 -25.7(10) . . . . ? O33 O2 Cl11 O4 -75.1(8) . . . . ? O21 O1 Cl11 Cl1 13(2) . . . . ? O31 O1 Cl11 Cl1 -15(3) . . . . ? O34 O1 Cl11 Cl1 154.0(14) . . . . ? O21 O1 Cl11 O22 123(2) . . . . ? O31 O1 Cl11 O22 95(2) . . . . ? Cl1 O1 Cl11 O22 109.3(18) . . . . ? O34 O1 Cl11 O22 -96.6(14) . . . . ? O21 O1 Cl11 O2 145(2) . . . . ? O31 O1 Cl11 O2 117(2) . . . . ? Cl1 O1 Cl11 O2 132(3) . . . . ? O34 O1 Cl11 O2 -74.1(18) . . . . ? O21 O1 Cl11 O23 -71(2) . . . . ? O31 O1 Cl11 O23 -99(2) . . . . ? Cl1 O1 Cl11 O23 -84.9(15) . . . . ? O34 O1 Cl11 O23 69.2(12) . . . . ? O21 O1 Cl11 O34 -141(2) . . . . ? O31 O1 Cl11 O34 -168.6(18) . . . . ? Cl1 O1 Cl11 O34 -154.0(14) . . . . ? O21 O1 Cl11 O32 113(2) . . . . ? O31 O1 Cl11 O32 85.3(17) . . . . ? Cl1 O1 Cl11 O32 99.9(15) . . . . ? O34 O1 Cl11 O32 -106.0(5) . . . . ? O21 O1 Cl11 O33 -35(2) . . . . ? O31 O1 Cl11 O33 -63(2) . . . . ? Cl1 O1 Cl11 O33 -48.6(13) . . . . ? O34 O1 Cl11 O33 105.4(7) . . . . ? O21 O1 Cl11 O31 28(3) . . . . ? Cl1 O1 Cl11 O31 15(3) . . . . ? O34 O1 Cl11 O31 168.6(18) . . . . ? O31 O1 Cl11 O21 -28(3) . . . . ? Cl1 O1 Cl11 O21 -13(2) . . . . ? O34 O1 Cl11 O21 141(2) . . . . ? O21 O1 Cl11 O3 -42.3(19) . . . . ? O31 O1 Cl11 O3 -70(2) . . . . ? Cl1 O1 Cl11 O3 -55.8(10) . . . . ? O34 O1 Cl11 O3 98.2(9) . . . . ? O21 O1 Cl11 O4 40.1(19) . . . . ? O31 O1 Cl11 O4 12(2) . . . . ? Cl1 O1 Cl11 O4 26.6(9) . . . . ? O34 O1 Cl11 O4 -179.3(8) . . . . ? O33 O23 Cl11 Cl1 21(3) . . . . ? O3 O23 Cl11 Cl1 -24.5(17) . . . . ? O34 O23 Cl11 Cl1 -164.6(13) . . . . ? O33 O23 Cl11 O22 -80(3) . . . . ? O3 O23 Cl11 O22 -126.0(17) . . . . ? Cl1 O23 Cl11 O22 -101.5(18) . . . . ? O34 O23 Cl11 O22 93.9(16) . . . . ? O33 O23 Cl11 O2 -82(2) . . . . ? O3 O23 Cl11 O2 -127.8(15) . . . . ? Cl1 O23 Cl11 O2 -103.3(13) . . . . ? O34 O23 Cl11 O2 92.1(9) . . . . ? O33 O23 Cl11 O1 117(2) . . . . ? O3 O23 Cl11 O1 71.2(16) . . . . ? Cl1 O23 Cl11 O1 95.7(14) . . . . ? O34 O23 Cl11 O1 -68.9(11) . . . . ? O33 O23 Cl11 O34 -174(2) . . . . ? O3 O23 Cl11 O34 140.1(17) . . . . ? Cl1 O23 Cl11 O34 164.6(13) . . . . ? O33 O23 Cl11 O32 -68(3) . . . . ? O3 O23 Cl11 O32 -114.1(17) . . . . ? Cl1 O23 Cl11 O32 -89.6(15) . . . . ? O34 O23 Cl11 O32 105.8(7) . . . . ? O3 O23 Cl11 O33 -45.7(19) . . . . ? Cl1 O23 Cl11 O33 -21(3) . . . . ? O34 O23 Cl11 O33 174(2) . . . . ? O33 O23 Cl11 O31 80(2) . . . . ? O3 O23 Cl11 O31 34.1(18) . . . . ? Cl1 O23 Cl11 O31 58.6(13) . . . . ? O34 O23 Cl11 O31 -106.0(6) . . . . ? O33 O23 Cl11 O21 92(2) . . . . ? O3 O23 Cl11 O21 45.9(15) . . . . ? Cl1 O23 Cl11 O21 70.4(12) . . . . ? O34 O23 Cl11 O21 -94.2(12) . . . . ? O33 O23 Cl11 O3 45.7(19) . . . . ? Cl1 O23 Cl11 O3 24.5(17) . . . . ? O34 O23 Cl11 O3 -140.1(17) . . . . ? O33 O23 Cl11 O4 12(3) . . . . ? O3 O23 Cl11 O4 -33.7(17) . . . . ? Cl1 O23 Cl11 O4 -9.2(7) . . . . ? O34 O23 Cl11 O4 -173.7(8) . . . . ? O1 O21 Cl11 Cl1 -166(2) . . . . ? O1 O21 Cl11 O22 -69(2) . . . . ? Cl1 O21 Cl11 O22 97.6(16) . . . . ? O1 O21 Cl11 O2 -82(4) . . . . ? Cl1 O21 Cl11 O2 85(4) . . . . ? Cl1 O21 Cl11 O1 166(2) . . . . ? O1 O21 Cl11 O23 119(2) . . . . ? Cl1 O21 Cl11 O23 -74.9(12) . . . . ? O1 O21 Cl11 O34 39(2) . . . . ? Cl1 O21 Cl11 O34 -155.0(13) . . . . ? O1 O21 Cl11 O32 -81(2) . . . . ? Cl1 O21 Cl11 O32 85.4(15) . . . . ? O1 O21 Cl11 O33 151.8(18) . . . . ? Cl1 O21 Cl11 O33 -42.0(12) . . . . ? O1 O21 Cl11 O31 -104(6) . . . . ? Cl1 O21 Cl11 O31 62(5) . . . . ? O1 O21 Cl11 O3 139.7(18) . . . . ? Cl1 O21 Cl11 O3 -54.2(9) . . . . ? O1 O21 Cl11 O4 -138.4(19) . . . . ? Cl1 O21 Cl11 O4 27.8(9) . . . . ? O33 O3 Cl11 Cl1 75(3) . . . . ? O23 O3 Cl11 Cl1 150(2) . . . . ? O33 O3 Cl11 O22 8(3) . . . . ? O23 O3 Cl11 O22 82(2) . . . . ? Cl1 O3 Cl11 O22 -67.8(18) . . . . ? O33 O3 Cl11 O2 -19(3) . . . . ? O23 O3 Cl11 O2 55.5(17) . . . . ? Cl1 O3 Cl11 O2 -94.4(13) . . . . ? O33 O3 Cl11 O1 165(2) . . . . ? O23 O3 Cl11 O1 -120.2(17) . . . . ? Cl1 O3 Cl11 O1 89.9(13) . . . . ? O33 O3 Cl11 O23 -74(2) . . . . ? Cl1 O3 Cl11 O23 -150(2) . . . . ? O33 O3 Cl11 O34 -114(2) . . . . ? O23 O3 Cl11 O34 -39.8(17) . . . . ? Cl1 O3 Cl11 O34 170.3(14) . . . . ? O33 O3 Cl11 O32 15(3) . . . . ? O23 O3 Cl11 O32 89(2) . . . . ? Cl1 O3 Cl11 O32 -60.4(15) . . . . ? O23 O3 Cl11 O33 74(2) . . . . ? Cl1 O3 Cl11 O33 -75(3) . . . . ? O33 O3 Cl11 O31 135(2) . . . . ? O23 O3 Cl11 O31 -150.5(17) . . . . ? Cl1 O3 Cl11 O31 59.6(13) . . . . ? O33 O3 Cl11 O21 149(2) . . . . ? O23 O3 Cl11 O21 -137.0(13) . . . . ? Cl1 O3 Cl11 O21 73.1(13) . . . . ? O33 O3 Cl11 O4 73(2) . . . . ? O23 O3 Cl11 O4 147.5(16) . . . . ? Cl1 O3 Cl11 O4 -2.4(9) . . . . ? O21 O1 O31 Cl1 -107(5) . . . . ? Cl11 O1 O31 Cl1 6.0(11) . . . . ? O34 O1 O31 Cl1 -11(4) . . . . ? O21 O1 O31 Cl11 -113(4) . . . . ? Cl1 O1 O31 Cl11 -6.0(11) . . . . ? O34 O1 O31 Cl11 -17(3) . . . . ? O21 O1 O31 O4 -129(6) . . . . ? Cl11 O1 O31 O4 -16(3) . . . . ? Cl1 O1 O31 O4 -22.1(16) . . . . ? O34 O1 O31 O4 -33(5) . . . . ? Cl11 Cl1 O31 O1 -13(2) . . . . ? O33 Cl1 O31 O1 100(2) . . . . ? O4 Cl1 O31 O1 -157.4(18) . . . . ? O3 Cl1 O31 O1 94.2(17) . . . . ? O2 Cl1 O31 O1 -51(2) . . . . ? O23 Cl1 O31 O1 60(2) . . . . ? O22 Cl1 O31 O1 -65.7(19) . . . . ? O21 Cl1 O31 O1 55(4) . . . . ? O24 Cl1 O31 O1 -178.1(16) . . . . ? O32 Cl1 O31 O1 -76.6(17) . . . . ? O33 Cl1 O31 Cl11 113(2) . . . . ? O4 Cl1 O31 Cl11 -144.1(11) . . . . ? O1 Cl1 O31 Cl11 13(2) . . . . ? O3 Cl1 O31 Cl11 107.5(12) . . . . ? O2 Cl1 O31 Cl11 -37.3(10) . . . . ? O23 Cl1 O31 Cl11 72.8(15) . . . . ? O22 Cl1 O31 Cl11 -52.4(13) . . . . ? O21 Cl1 O31 Cl11 68(5) . . . . ? O24 Cl1 O31 Cl11 -164.8(14) . . . . ? O32 Cl1 O31 Cl11 -63.3(11) . . . . ? Cl11 Cl1 O31 O4 144.1(11) . . . . ? O33 Cl1 O31 O4 -102.6(17) . . . . ? O1 Cl1 O31 O4 157.4(18) . . . . ? O3 Cl1 O31 O4 -108.4(4) . . . . ? O2 Cl1 O31 O4 106.9(8) . . . . ? O23 Cl1 O31 O4 -143.0(10) . . . . ? O22 Cl1 O31 O4 91.7(7) . . . . ? O21 Cl1 O31 O4 -148(5) . . . . ? O24 Cl1 O31 O4 -20.7(8) . . . . ? O32 Cl1 O31 O4 80.8(8) . . . . ? Cl1 Cl11 O31 O1 164(3) . . . . ? O22 Cl11 O31 O1 -97.4(19) . . . . ? O2 Cl11 O31 O1 -116(2) . . . . ? O23 Cl11 O31 O1 99(2) . . . . ? O34 Cl11 O31 O1 11.8(19) . . . . ? O32 Cl11 O31 O1 -108.3(19) . . . . ? O33 Cl11 O31 O1 131.9(19) . . . . ? O21 Cl11 O31 O1 51(4) . . . . ? O3 Cl11 O31 O1 115.0(18) . . . . ? O4 Cl11 O31 O1 -166(2) . . . . ? O22 Cl11 O31 Cl1 98.1(17) . . . . ? O2 Cl11 O31 Cl1 79(2) . . . . ? O1 Cl11 O31 Cl1 -164(3) . . . . ? O23 Cl11 O31 Cl1 -65.6(14) . . . . ? O34 Cl11 O31 Cl1 -152.6(14) . . . . ? O32 Cl11 O31 Cl1 87.2(14) . . . . ? O33 Cl11 O31 Cl1 -32.6(14) . . . . ? O21 Cl11 O31 Cl1 -114(5) . . . . ? O3 Cl11 O31 Cl1 -49.5(11) . . . . ? O4 Cl11 O31 Cl1 29.1(9) . . . . ? Cl1 Cl11 O31 O4 -29.1(9) . . . . ? O22 Cl11 O31 O4 69.0(13) . . . . ? O2 Cl11 O31 O4 50.3(18) . . . . ? O1 Cl11 O31 O4 166(2) . . . . ? O23 Cl11 O31 O4 -94.6(11) . . . . ? O34 Cl11 O31 O4 178.3(9) . . . . ? O32 Cl11 O31 O4 58.2(9) . . . . ? O33 Cl11 O31 O4 -61.7(9) . . . . ? O21 Cl11 O31 O4 -143(5) . . . . ? O3 Cl11 O31 O4 -78.5(6) . . . . ? O24 O4 O31 O1 78(4) . . . . ? Cl1 O4 O31 O1 28(2) . . . . ? Cl11 O4 O31 O1 14(2) . . . . ? O24 O4 O31 Cl1 50.3(19) . . . . ? Cl11 O4 O31 Cl1 -13.9(4) . . . . ? O24 O4 O31 Cl11 64.2(18) . . . . ? Cl1 O4 O31 Cl11 13.9(4) . . . . ? O22 O2 O32 Cl11 -44(5) . . . . ? Cl1 O2 O32 Cl11 22.2(5) . . . . ? O33 O2 O32 Cl11 43.5(8) . . . . ? O22 O2 O32 Cl1 -66(5) . . . . ? Cl11 O2 O32 Cl1 -22.2(5) . . . . ? O33 O2 O32 Cl1 21.3(10) . . . . ? Cl1 Cl11 O32 O2 -105.0(17) . . . . ? O22 Cl11 O32 O2 93(9) . . . . ? O1 Cl11 O32 O2 152.4(14) . . . . ? O23 Cl11 O32 O2 -22.5(15) . . . . ? O34 Cl11 O32 O2 66.8(14) . . . . ? O33 Cl11 O32 O2 -53.4(14) . . . . ? O31 Cl11 O32 O2 -173.2(14) . . . . ? O21 Cl11 O32 O2 -179.6(16) . . . . ? O3 Cl11 O32 O2 -59.6(15) . . . . ? O4 Cl11 O32 O2 -120.8(14) . . . . ? O22 Cl11 O32 Cl1 -162(9) . . . . ? O2 Cl11 O32 Cl1 105.0(17) . . . . ? O1 Cl11 O32 Cl1 -102.6(14) . . . . ? O23 Cl11 O32 Cl1 82.5(15) . . . . ? O34 Cl11 O32 Cl1 171.7(14) . . . . ? O33 Cl11 O32 Cl1 51.5(13) . . . . ? O31 Cl11 O32 Cl1 -68.2(14) . . . . ? O21 Cl11 O32 Cl1 -74.6(15) . . . . ? O3 Cl11 O32 Cl1 45.4(11) . . . . ? O4 Cl11 O32 Cl1 -15.9(9) . . . . ? Cl11 Cl1 O32 O2 63.8(16) . . . . ? O33 Cl1 O32 O2 -32.6(16) . . . . ? O31 Cl1 O32 O2 144.9(12) . . . . ? O4 Cl1 O32 O2 -136.7(12) . . . . ? O1 Cl1 O32 O2 113.2(11) . . . . ? O3 Cl1 O32 O2 -21.4(18) . . . . ? O23 Cl1 O32 O2 3.2(16) . . . . ? O22 Cl1 O32 O2 77(6) . . . . ? O21 Cl1 O32 O2 132.0(12) . . . . ? O24 Cl1 O32 O2 -112.0(12) . . . . ? O33 Cl1 O32 Cl11 -96.4(16) . . . . ? O31 Cl1 O32 Cl11 81.1(13) . . . . ? O4 Cl1 O32 Cl11 159.5(11) . . . . ? O1 Cl1 O32 Cl11 49.4(11) . . . . ? O3 Cl1 O32 Cl11 -85.2(14) . . . . ? O2 Cl1 O32 Cl11 -63.8(16) . . . . ? O23 Cl1 O32 Cl11 -60.6(13) . . . . ? O22 Cl1 O32 Cl11 13(7) . . . . ? O21 Cl1 O32 Cl11 68.2(14) . . . . ? O24 Cl1 O32 Cl11 -175.8(13) . . . . ? Cl1 O3 O33 O23 89.8(18) . . . . ? Cl11 O3 O33 O23 67.8(16) . . . . ? O23 O3 O33 Cl1 -89.8(18) . . . . ? Cl11 O3 O33 Cl1 -22.0(5) . . . . ? O23 O3 O33 Cl11 -67.8(16) . . . . ? Cl1 O3 O33 Cl11 22.0(5) . . . . ? O23 O3 O33 O24 -149(2) . . . . ? Cl1 O3 O33 O24 -59.2(13) . . . . ? Cl11 O3 O33 O24 -81.2(14) . . . . ? O23 O3 O33 O2 -50(3) . . . . ? Cl1 O3 O33 O2 40(2) . . . . ? Cl11 O3 O33 O2 18(2) . . . . ? Cl11 O23 O33 O3 -106.1(16) . . . . ? Cl1 O23 O33 O3 -96(2) . . . . ? O34 O23 O33 O3 -112(3) . . . . ? O3 O23 O33 Cl1 96(2) . . . . ? Cl11 O23 O33 Cl1 -9.7(11) . . . . ? O34 O23 O33 Cl1 -15(3) . . . . ? O3 O23 O33 Cl11 106.1(16) . . . . ? Cl1 O23 O33 Cl11 9.7(11) . . . . ? O34 O23 O33 Cl11 -6(2) . . . . ? O3 O23 O33 O24 84(6) . . . . ? Cl11 O23 O33 O24 -22(5) . . . . ? Cl1 O23 O33 O24 -13(4) . . . . ? O34 O23 O33 O24 -28(8) . . . . ? O3 O23 O33 O2 148.3(18) . . . . ? Cl11 O23 O33 O2 42.2(5) . . . . ? Cl1 O23 O33 O2 51.9(9) . . . . ? O34 O23 O33 O2 37(3) . . . . ? Cl11 Cl1 O33 O3 95(2) . . . . ? O31 Cl1 O33 O3 -12(3) . . . . ? O4 Cl1 O33 O3 -105(2) . . . . ? O1 Cl1 O33 O3 35(3) . . . . ? O2 Cl1 O33 O3 147(2) . . . . ? O23 Cl1 O33 O3 70(3) . . . . ? O22 Cl1 O33 O3 152.1(19) . . . . ? O21 Cl1 O33 O3 2(3) . . . . ? O24 Cl1 O33 O3 -103(2) . . . . ? O32 Cl1 O33 O3 164.5(18) . . . . ? Cl11 Cl1 O33 O23 26(3) . . . . ? O31 Cl1 O33 O23 -82(3) . . . . ? O4 Cl1 O33 O23 -175(2) . . . . ? O1 Cl1 O33 O23 -35(3) . . . . ? O3 Cl1 O33 O23 -70(3) . . . . ? O2 Cl1 O33 O23 77(2) . . . . ? O22 Cl1 O33 O23 82(2) . . . . ? O21 Cl1 O33 O23 -68(3) . . . . ? O24 Cl1 O33 O23 -173(3) . . . . ? O32 Cl1 O33 O23 95(2) . . . . ? O31 Cl1 O33 Cl11 -107(2) . . . . ? O4 Cl1 O33 Cl11 159.7(15) . . . . ? O1 Cl1 O33 Cl11 -60.6(14) . . . . ? O3 Cl1 O33 Cl11 -95(2) . . . . ? O2 Cl1 O33 Cl11 51.5(13) . . . . ? O23 Cl1 O33 Cl11 -26(3) . . . . ? O22 Cl1 O33 Cl11 56.7(14) . . . . ? O21 Cl1 O33 Cl11 -93.7(17) . . . . ? O24 Cl1 O33 Cl11 161.8(14) . . . . ? O32 Cl1 O33 Cl11 69.2(14) . . . . ? Cl11 Cl1 O33 O24 -161.8(14) . . . . ? O31 Cl1 O33 O24 91.0(18) . . . . ? O4 Cl1 O33 O24 -2.1(10) . . . . ? O1 Cl1 O33 O24 137.5(11) . . . . ? O3 Cl1 O33 O24 103(2) . . . . ? O2 Cl1 O33 O24 -110.3(8) . . . . ? O23 Cl1 O33 O24 173(3) . . . . ? O22 Cl1 O33 O24 -105.1(7) . . . . ? O21 Cl1 O33 O24 104.4(8) . . . . ? O32 Cl1 O33 O24 -92.7(12) . . . . ? Cl11 Cl1 O33 O2 -51.5(13) . . . . ? O31 Cl1 O33 O2 -158.7(16) . . . . ? O4 Cl1 O33 O2 108.2(4) . . . . ? O1 Cl1 O33 O2 -112.2(10) . . . . ? O3 Cl1 O33 O2 -147(2) . . . . ? O23 Cl1 O33 O2 -77(2) . . . . ? O22 Cl1 O33 O2 5.2(10) . . . . ? O21 Cl1 O33 O2 -145.2(11) . . . . ? O24 Cl1 O33 O2 110.3(8) . . . . ? O32 Cl1 O33 O2 17.6(9) . . . . ? Cl1 Cl11 O33 O3 -88(3) . . . . ? O22 Cl11 O33 O3 -175(2) . . . . ? O2 Cl11 O33 O3 162(2) . . . . ? O1 Cl11 O33 O3 -18(2) . . . . ? O23 Cl11 O33 O3 66(2) . . . . ? O34 Cl11 O33 O3 72(2) . . . . ? O32 Cl11 O33 O3 -168(2) . . . . ? O31 Cl11 O33 O3 -48(2) . . . . ? O21 Cl11 O33 O3 -33(2) . . . . ? O4 Cl11 O33 O3 -102(2) . . . . ? Cl1 Cl11 O33 O23 -153(3) . . . . ? O22 Cl11 O33 O23 120(2) . . . . ? O2 Cl11 O33 O23 96(2) . . . . ? O1 Cl11 O33 O23 -84(3) . . . . ? O34 Cl11 O33 O23 6(3) . . . . ? O32 Cl11 O33 O23 126(3) . . . . ? O31 Cl11 O33 O23 -114(3) . . . . ? O21 Cl11 O33 O23 -99(2) . . . . ? O3 Cl11 O33 O23 -66(2) . . . . ? O4 Cl11 O33 O23 -168(3) . . . . ? O22 Cl11 O33 Cl1 -87.0(19) . . . . ? O2 Cl11 O33 Cl1 -110.7(16) . . . . ? O1 Cl11 O33 Cl1 69.5(15) . . . . ? O23 Cl11 O33 Cl1 153(3) . . . . ? O34 Cl11 O33 Cl1 159.1(16) . . . . ? O32 Cl11 O33 Cl1 -80.6(16) . . . . ? O31 Cl11 O33 Cl1 39.1(16) . . . . ? O21 Cl11 O33 Cl1 54.6(15) . . . . ? O3 Cl11 O33 Cl1 88(3) . . . . ? O4 Cl11 O33 Cl1 -15.0(11) . . . . ? Cl1 Cl11 O33 O24 15.7(12) . . . . ? O22 Cl11 O33 O24 -71.3(15) . . . . ? O2 Cl11 O33 O24 -95.0(11) . . . . ? O1 Cl11 O33 O24 85.2(12) . . . . ? O23 Cl11 O33 O24 169(3) . . . . ? O34 Cl11 O33 O24 174.8(11) . . . . ? O32 Cl11 O33 O24 -64.9(12) . . . . ? O31 Cl11 O33 O24 54.8(12) . . . . ? O21 Cl11 O33 O24 70.3(11) . . . . ? O3 Cl11 O33 O24 103(2) . . . . ? O4 Cl11 O33 O24 0.7(8) . . . . ? Cl1 Cl11 O33 O2 110.7(16) . . . . ? O22 Cl11 O33 O2 23.7(12) . . . . ? O1 Cl11 O33 O2 -179.8(12) . . . . ? O23 Cl11 O33 O2 -96(2) . . . . ? O34 Cl11 O33 O2 -90.2(9) . . . . ? O32 Cl11 O33 O2 30.1(8) . . . . ? O31 Cl11 O33 O2 149.8(9) . . . . ? O21 Cl11 O33 O2 165.4(12) . . . . ? O3 Cl11 O33 O2 -162(2) . . . . ? O4 Cl11 O33 O2 95.8(6) . . . . ? O4 O24 O33 O3 94(3) . . . . ? Cl1 O24 O33 O3 89(2) . . . . ? Cl11 O24 O33 O3 96(2) . . . . ? O4 O24 O33 O23 19(7) . . . . ? Cl1 O24 O33 O23 15(5) . . . . ? Cl11 O24 O33 O23 22(5) . . . . ? O4 O24 O33 Cl1 5(2) . . . . ? Cl11 O24 O33 Cl1 6.8(5) . . . . ? O4 O24 O33 Cl11 -2(2) . . . . ? Cl1 O24 O33 Cl11 -6.8(5) . . . . ? O4 O24 O33 O2 -44(2) . . . . ? Cl1 O24 O33 O2 -48.6(6) . . . . ? Cl11 O24 O33 O2 -41.9(5) . . . . ? O22 O2 O33 O3 -62(4) . . . . ? O32 O2 O33 O3 -86(4) . . . . ? Cl11 O2 O33 O3 -27(3) . . . . ? Cl1 O2 O33 O3 -53(3) . . . . ? O22 O2 O33 O23 -108(2) . . . . ? O32 O2 O33 O23 -133(2) . . . . ? Cl11 O2 O33 O23 -74(2) . . . . ? Cl1 O2 O33 O23 -100(2) . . . . ? O22 O2 O33 Cl1 -8.8(16) . . . . ? O32 O2 O33 Cl1 -33.2(16) . . . . ? Cl11 O2 O33 Cl1 25.9(7) . . . . ? O22 O2 O33 Cl11 -34.7(15) . . . . ? O32 O2 O33 Cl11 -59.0(14) . . . . ? Cl1 O2 O33 Cl11 -25.9(7) . . . . ? O22 O2 O33 O24 44.6(19) . . . . ? O32 O2 O33 O24 20.2(18) . . . . ? Cl11 O2 O33 O24 79.2(11) . . . . ? Cl1 O2 O33 O24 53.4(9) . . . . ? Cl1 Cl11 O34 O1 -86(3) . . . . ? O22 Cl11 O34 O1 109.0(14) . . . . ? O2 Cl11 O34 O1 148.4(10) . . . . ? O23 Cl11 O34 O1 -123.2(12) . . . . ? O32 Cl11 O34 O1 113.5(10) . . . . ? O33 Cl11 O34 O1 -126.4(10) . . . . ? O31 Cl11 O34 O1 -6.4(10) . . . . ? O21 Cl11 O34 O1 -15.9(9) . . . . ? O3 Cl11 O34 O1 -104.3(8) . . . . ? Cl1 Cl11 O34 O23 37(3) . . . . ? O22 Cl11 O34 O23 -127.9(12) . . . . ? O2 Cl11 O34 O23 -88.5(10) . . . . ? O1 Cl11 O34 O23 123.2(12) . . . . ? O32 Cl11 O34 O23 -123.3(14) . . . . ? O33 Cl11 O34 O23 -3.2(13) . . . . ? O31 Cl11 O34 O23 116.7(14) . . . . ? O21 Cl11 O34 O23 107.2(9) . . . . ? O3 Cl11 O34 O23 18.8(9) . . . . ? O22 Cl11 O34 Cl1 -165(4) . . . . ? O2 Cl11 O34 Cl1 -126(3) . . . . ? O1 Cl11 O34 Cl1 86(3) . . . . ? O23 Cl11 O34 Cl1 -37(3) . . . . ? O32 Cl11 O34 Cl1 -161(3) . . . . ? O33 Cl11 O34 Cl1 -41(3) . . . . ? O31 Cl11 O34 Cl1 79(3) . . . . ? O21 Cl11 O34 Cl1 70(3) . . . . ? O3 Cl11 O34 Cl1 -19(3) . . . . ? O21 O1 O34 Cl11 69(2) . . . . ? O31 O1 O34 Cl11 20(3) . . . . ? Cl1 O1 O34 Cl11 10.0(5) . . . . ? O21 O1 O34 O23 28(3) . . . . ? O31 O1 O34 O23 -20(4) . . . . ? Cl11 O1 O34 O23 -40.7(9) . . . . ? Cl1 O1 O34 O23 -30.7(8) . . . . ? O21 O1 O34 Cl1 59(2) . . . . ? O31 O1 O34 Cl1 10(3) . . . . ? Cl11 O1 O34 Cl1 -10.0(5) . . . . ? O33 O23 O34 Cl11 7(3) . . . . ? O3 O23 O34 Cl11 -55(2) . . . . ? Cl1 O23 O34 Cl11 -6.1(5) . . . . ? O33 O23 O34 O1 44(3) . . . . ? O3 O23 O34 O1 -18(2) . . . . ? Cl11 O23 O34 O1 36.9(8) . . . . ? Cl1 O23 O34 O1 30.8(7) . . . . ? O33 O23 O34 Cl1 13(3) . . . . ? O3 O23 O34 Cl1 -49.0(19) . . . . ? Cl11 O23 O34 Cl1 6.1(5) . . . . ? C27 C21 C22 C23 -177.2(12) . . . . ? C26 C21 C22 C23 -1.6(16) . . . . ? C21 C22 C23 C24 1.4(17) . . . . ? C21 C22 C23 C28 -178.2(11) . . . . ? C22 C23 C24 C25 -1.2(17) . . . . ? C28 C23 C24 C25 178.5(12) . . . . ? C23 C24 C25 C26 1.3(19) . . . . ? C24 C25 C26 C21 -1.5(18) . . . . ? C22 C21 C26 C25 1.6(16) . . . . ? C27 C21 C26 C25 177.1(11) . . . . ? C36 C31 C32 C33 0.0 . . . . ? C37 C31 C32 C33 173(3) . . . . ? C31 C32 C33 C34 0.0 . . . . ? C32 C33 C34 C35 0.0 . . . . ? C32 C33 C34 C38 171(2) . . . . ? C33 C34 C35 C36 0.0 . . . . ? C38 C34 C35 C36 -167(3) . . . . ? C34 C35 C36 C31 0.0 . . . . ? C32 C31 C36 C35 0.0 . . . . ? C37 C31 C36 C35 -175(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 949087' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; bis(\m~2~-4-(E)-(4-chlorobenzylidene)amino-4H-1,2,4-triazole)-bis((E)-4-(chlor obenzylidene)amino-4H-1,2,4-triazole)-di-copper(i) diperchlorate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H28 Cl4 Cu2 N16, 2(Cl O4)' _chemical_formula_sum 'C36 H28 Cl6 Cu2 N16 O8' _chemical_formula_weight 1152.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.093(2) _cell_length_b 18.185(3) _cell_length_c 18.270(3) _cell_angle_alpha 90 _cell_angle_beta 90.40(3) _cell_angle_gamma 90 _cell_volume 2356.5(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 281 _cell_measurement_theta_min 2.4168 _cell_measurement_theta_max 75.2969 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.624 _exptl_crystal_F_000 1160 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_absorpt_coefficient_mu 4.824 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _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 293(2) _diffrn_radiation_wavelength 1.54175 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Onyx' _diffrn_measurement_method '\w scans' _diffrn_reflns_number 6247 _diffrn_reflns_av_unetI/netI 0.4134 _diffrn_reflns_av_R_equivalents 0.1129 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.429 _diffrn_reflns_theta_max 75.523 _diffrn_reflns_theta_full 67.676 _diffrn_measured_fraction_theta_max 0.745 _diffrn_measured_fraction_theta_full 0.795 _diffrn_reflns_Laue_measured_fraction_max 0.745 _diffrn_reflns_Laue_measured_fraction_full 0.795 _diffrn_reflns_point_group_measured_fraction_max 0.745 _diffrn_reflns_point_group_measured_fraction_full 0.795 _reflns_number_total 3636 _reflns_number_gt 473 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET) (compiled Aug 14 2012,18:12:40) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET) (compiled Aug 14 2012,18:12:40) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21t (release 14-08-2012 CrysAlis171 .NET) (compiled Aug 14 2012,18:12:40) ; _computing_structure_solution 'SHELXS-2013 (Sheldrick, 2013)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0560P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 3636 _refine_ls_number_parameters 170 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.2944 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.1669 _refine_ls_wR_factor_gt 0.1244 _refine_ls_goodness_of_fit_ref 0.531 _refine_ls_restrained_S_all 0.530 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.4297(3) 0.08393(11) 0.53575(11) 0.1310(9) Uani 1 1 d . . . . . Cl5 Cl 0.8597(6) 0.2119(3) -0.0912(3) 0.215(2) Uani 1 1 d . . . . . Cl15 Cl 0.0824(5) 0.5772(3) 0.9164(2) 0.193(2) Uani 1 1 d . . . . . N1 N 0.5857(14) 0.0091(6) 0.4056(6) 0.115(4) Uiso 1 1 d . . . . . N2 N 0.5293(12) 0.0769(6) 0.4362(5) 0.103(3) Uiso 1 1 d . . . . . N3 N 0.6221(12) 0.0877(6) 0.3199(5) 0.092(3) Uiso 1 1 d . . . . . N4 N 0.6576(12) 0.1218(5) 0.2582(5) 0.095(3) Uiso 1 1 d . . . . . N11 N 0.3420(14) 0.1881(6) 0.5498(6) 0.120(4) Uiso 1 1 d . . . . . N12 N 0.3481(14) 0.2311(7) 0.4869(6) 0.136(4) Uiso 1 1 d . . . . . N13 N 0.2799(13) 0.2938(6) 0.5885(6) 0.104(3) Uiso 1 1 d . . . . . N14 N 0.2361(13) 0.3540(6) 0.6322(5) 0.104(3) Uiso 1 1 d . . . . . C1 C 0.6810(14) 0.0901(7) 0.2009(6) 0.113(4) Uiso 1 1 d . . . . . H1A H 0.6707 0.0393 0.2043 0.135 Uiso 1 1 calc R U . . . C2 C 0.7206(17) 0.1152(8) 0.1308(7) 0.108(5) Uiso 1 1 d . . . . . C3 C 0.7526(16) 0.1930(8) 0.1233(7) 0.122(5) Uiso 1 1 d . . . . . H3A H 0.7468 0.2249 0.1631 0.147 Uiso 1 1 calc R U . . . C4 C 0.7929(15) 0.2177(8) 0.0527(7) 0.128(5) Uiso 1 1 d . . . . . H4A H 0.8084 0.2682 0.0476 0.154 Uiso 1 1 calc R U . . . C5 C 0.8116(19) 0.1788(9) -0.0071(8) 0.140(6) Uiso 1 1 d . . . . . C6 C 0.7825(17) 0.1027(9) 0.0020(8) 0.158(6) Uiso 1 1 d . . . . . H6A H 0.7889 0.0711 -0.0379 0.190 Uiso 1 1 calc R U . . . C7 C 0.7444(15) 0.0760(8) 0.0710(8) 0.140(5) Uiso 1 1 d . . . . . H7A H 0.7346 0.0252 0.0757 0.168 Uiso 1 1 calc R U . . . C8 C 0.6354(15) 0.0149(7) 0.3394(6) 0.099(4) Uiso 1 1 d . . . . . H8A H 0.6741 -0.0234 0.3092 0.119 Uiso 1 1 calc R U . . . C9 C 0.5681(15) 0.1169(7) 0.3819(6) 0.102(4) Uiso 1 1 d . . . . . H9A H 0.5581 0.1677 0.3858 0.122 Uiso 1 1 calc R U . . . C11 C 0.2004(14) 0.3423(6) 0.6966(6) 0.095(4) Uiso 1 1 d . . . . . H11A H 0.1992 0.2937 0.7124 0.114 Uiso 1 1 calc R U . . . C12 C 0.1595(15) 0.4000(6) 0.7505(6) 0.090(4) Uiso 1 1 d . . . . . C13 C 0.1812(16) 0.4770(7) 0.7266(6) 0.114(4) Uiso 1 1 d . . . . . H13A H 0.2133 0.4899 0.6791 0.137 Uiso 1 1 calc R U . . . C14 C 0.1507(15) 0.5269(7) 0.7794(7) 0.113(5) Uiso 1 1 d . . . . . H14A H 0.1591 0.5762 0.7661 0.135 Uiso 1 1 calc R U . . . C15 C 0.1109(17) 0.5131(7) 0.8467(7) 0.107(4) Uiso 1 1 d . . . . . C16 C 0.0921(17) 0.4373(8) 0.8742(7) 0.133(5) Uiso 1 1 d . . . . . H16A H 0.0617 0.4258 0.9223 0.159 Uiso 1 1 calc R U . . . C17 C 0.1241(15) 0.3860(7) 0.8215(7) 0.107(4) Uiso 1 1 d . . . . . H17A H 0.1214 0.3369 0.8357 0.129 Uiso 1 1 calc R U . . . C18 C 0.3064(16) 0.2208(8) 0.6106(7) 0.125(5) Uiso 1 1 d . . . . . H18A H 0.2998 0.2010 0.6574 0.150 Uiso 1 1 calc R U . . . C19 C 0.3059(16) 0.2934(7) 0.5194(7) 0.117(5) Uiso 1 1 d . . . . . H19A H 0.2952 0.3366 0.4925 0.140 Uiso 1 1 calc R U . . . Cl1 Cl 0.3670(10) 0.3573(3) 0.3054(3) 0.177(2) Uani 1 1 d . . . . . O1 O 0.514(3) 0.3614(10) 0.2483(11) 0.211(7) Uiso 0.676(11) 1 d . U P A 1 O2 O 0.370(4) 0.3944(12) 0.3703(10) 0.217(7) Uiso 0.676(11) 1 d . U P A 1 O3 O 0.205(3) 0.3692(12) 0.2670(14) 0.201(7) Uiso 0.676(11) 1 d . U P A 1 O11 O 0.510(6) 0.402(2) 0.334(2) 0.210(8) Uiso 0.324(11) 1 d . U P A 2 O21 O 0.176(6) 0.388(2) 0.3694(18) 0.212(8) Uiso 0.324(11) 1 d . U P A 2 O31 O 0.288(8) 0.376(2) 0.238(2) 0.203(8) Uiso 0.324(11) 1 d . U P A 2 O4 O 0.3540(18) 0.2900(8) 0.3229(6) 0.220(6) 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 0.1390(19) 0.0879(13) 0.166(2) -0.0140(15) -0.0244(13) 0.0050(17) Cl5 0.156(4) 0.264(6) 0.225(5) 0.085(4) 0.014(3) -0.011(4) Cl15 0.138(4) 0.182(4) 0.259(5) -0.106(4) -0.019(3) 0.024(4) Cl1 0.223(7) 0.131(4) 0.175(6) 0.025(4) -0.035(5) -0.012(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 1.960(9) . ? Cu1 N1 2.007(11) 3_656 ? Cu1 N11 2.011(11) . ? Cl5 C5 1.687(14) . ? Cl15 C15 1.739(12) . ? N1 C8 1.266(11) . ? N1 N2 1.413(12) . ? N1 Cu1 2.007(10) 3_656 ? N2 C9 1.263(12) . ? N3 C9 1.310(11) . ? N3 N4 1.313(10) . ? N3 C8 1.373(14) . ? N4 C1 1.208(11) . ? N11 C18 1.286(12) . ? N11 N12 1.392(12) . ? N12 C19 1.314(14) . ? N13 C19 1.278(11) . ? N13 N14 1.391(11) . ? N13 C18 1.398(14) . ? N14 C11 1.224(11) . ? C1 C2 1.390(13) . ? C1 H1A 0.9300 . ? C2 C7 1.317(14) . ? C2 C3 1.439(14) . ? C3 C4 1.397(13) . ? C3 H3A 0.9300 . ? C4 C5 1.310(15) . ? C4 H4A 0.9300 . ? C5 C6 1.409(17) . ? C6 C7 1.380(14) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? C9 H9A 0.9300 . ? C11 C12 1.471(12) . ? C11 H11A 0.9300 . ? C12 C17 1.346(12) . ? C12 C13 1.475(14) . ? C13 C14 1.342(13) . ? C13 H13A 0.9300 . ? C14 C15 1.288(13) . ? C14 H14A 0.9300 . ? C15 C16 1.473(16) . ? C16 C17 1.362(14) . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? Cl1 O4 1.268(13) . ? Cl1 O3 1.36(2) . ? Cl1 O2 1.363(19) . ? Cl1 O11 1.40(5) . ? Cl1 O31 1.39(5) . ? Cl1 O1 1.483(18) . ? Cl1 O21 1.88(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N1 117.5(4) . 3_656 ? N2 Cu1 N11 107.1(5) . . ? N1 Cu1 N11 135.1(4) 3_656 . ? C8 N1 N2 112.8(11) . . ? C8 N1 Cu1 126.6(10) . 3_656 ? N2 N1 Cu1 120.5(8) . 3_656 ? C9 N2 N1 97.3(10) . . ? C9 N2 Cu1 140.7(10) . . ? N1 N2 Cu1 122.0(9) . . ? C9 N3 N4 127.5(12) . . ? C9 N3 C8 100.9(10) . . ? N4 N3 C8 131.6(11) . . ? C1 N4 N3 123.3(12) . . ? C18 N11 N12 117.4(12) . . ? C18 N11 Cu1 127.5(11) . . ? N12 N11 Cu1 114.4(9) . . ? C19 N12 N11 95.9(10) . . ? C19 N13 N14 127.2(12) . . ? C19 N13 C18 105.1(11) . . ? N14 N13 C18 127.7(12) . . ? C11 N14 N13 117.5(12) . . ? N4 C1 C2 132.3(15) . . ? N4 C1 H1A 113.9 . . ? C2 C1 H1A 113.9 . . ? C7 C2 C1 127.9(15) . . ? C7 C2 C3 115.6(13) . . ? C1 C2 C3 116.3(13) . . ? C4 C3 C2 115.9(12) . . ? C4 C3 H3A 122.0 . . ? C2 C3 H3A 122.0 . . ? C5 C4 C3 128.3(15) . . ? C5 C4 H4A 115.9 . . ? C3 C4 H4A 115.9 . . ? C4 C5 C6 114.5(15) . . ? C4 C5 Cl5 126.2(15) . . ? C6 C5 Cl5 119.2(14) . . ? C7 C6 C5 119.0(15) . . ? C7 C6 H6A 120.5 . . ? C5 C6 H6A 120.5 . . ? C2 C7 C6 126.4(15) . . ? C2 C7 H7A 116.8 . . ? C6 C7 H7A 116.8 . . ? N1 C8 N3 107.9(11) . . ? N1 C8 H8A 126.0 . . ? N3 C8 H8A 126.0 . . ? N2 C9 N3 120.8(12) . . ? N2 C9 H9A 119.6 . . ? N3 C9 H9A 119.6 . . ? N14 C11 C12 124.2(12) . . ? N14 C11 H11A 117.9 . . ? C12 C11 H11A 117.9 . . ? C17 C12 C11 123.2(12) . . ? C17 C12 C13 119.1(12) . . ? C11 C12 C13 117.3(11) . . ? C14 C13 C12 114.3(12) . . ? C14 C13 H13A 122.9 . . ? C12 C13 H13A 122.9 . . ? C15 C14 C13 126.2(14) . . ? C15 C14 H14A 116.9 . . ? C13 C14 H14A 116.9 . . ? C14 C15 C16 121.9(13) . . ? C14 C15 Cl15 126.6(12) . . ? C16 C15 Cl15 111.5(10) . . ? C17 C16 C15 112.6(12) . . ? C17 C16 H16A 123.7 . . ? C15 C16 H16A 123.7 . . ? C12 C17 C16 125.7(13) . . ? C12 C17 H17A 117.2 . . ? C16 C17 H17A 117.2 . . ? N11 C18 N13 102.5(12) . . ? N11 C18 H18A 128.7 . . ? N13 C18 H18A 128.7 . . ? N13 C19 N12 119.1(14) . . ? N13 C19 H19A 120.5 . . ? N12 C19 H19A 120.5 . . ? O4 Cl1 O3 102.8(13) . . ? O4 Cl1 O2 105.1(11) . . ? O3 Cl1 O2 112.3(15) . . ? O4 Cl1 O11 121.5(19) . . ? O4 Cl1 O31 115(2) . . ? O11 Cl1 O31 118(3) . . ? O4 Cl1 O1 106.2(11) . . ? O3 Cl1 O1 102.9(13) . . ? O2 Cl1 O1 125.3(14) . . ? O4 Cl1 O21 94.2(13) . . ? O11 Cl1 O21 97(2) . . ? O31 Cl1 O21 101(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 N2 C9 -4.5(14) . . . . ? Cu1 N1 N2 C9 178.4(8) 3_656 . . . ? C8 N1 N2 Cu1 176.0(8) . . . . ? Cu1 N1 N2 Cu1 -1.2(12) 3_656 . . . ? C9 N3 N4 C1 -169.2(11) . . . . ? C8 N3 N4 C1 13(2) . . . . ? C18 N11 N12 C19 -1.6(14) . . . . ? Cu1 N11 N12 C19 -172.7(8) . . . . ? C19 N13 N14 C11 173.8(11) . . . . ? C18 N13 N14 C11 -6.7(19) . . . . ? N3 N4 C1 C2 -179.5(11) . . . . ? N4 C1 C2 C7 179.8(13) . . . . ? N4 C1 C2 C3 5(2) . . . . ? C7 C2 C3 C4 4.0(18) . . . . ? C1 C2 C3 C4 179.8(11) . . . . ? C2 C3 C4 C5 -3(2) . . . . ? C3 C4 C5 C6 2(2) . . . . ? C3 C4 C5 Cl5 179.8(10) . . . . ? C4 C5 C6 C7 -2(2) . . . . ? Cl5 C5 C6 C7 179.6(9) . . . . ? C1 C2 C7 C6 179.6(12) . . . . ? C3 C2 C7 C6 -5(2) . . . . ? C5 C6 C7 C2 4(2) . . . . ? N2 N1 C8 N3 1.7(14) . . . . ? Cu1 N1 C8 N3 178.6(7) 3_656 . . . ? C9 N3 C8 N1 1.8(13) . . . . ? N4 N3 C8 N1 179.8(11) . . . . ? N1 N2 C9 N3 6.2(14) . . . . ? Cu1 N2 C9 N3 -174.4(8) . . . . ? N4 N3 C9 N2 176.3(10) . . . . ? C8 N3 C9 N2 -5.6(14) . . . . ? N13 N14 C11 C12 177.3(10) . . . . ? N14 C11 C12 C17 -178.7(11) . . . . ? N14 C11 C12 C13 -6.2(18) . . . . ? C17 C12 C13 C14 -4.0(19) . . . . ? C11 C12 C13 C14 -176.9(10) . . . . ? C12 C13 C14 C15 2(2) . . . . ? C13 C14 C15 C16 -1(2) . . . . ? C13 C14 C15 Cl15 176.7(10) . . . . ? C14 C15 C16 C17 1(2) . . . . ? Cl15 C15 C16 C17 -176.6(9) . . . . ? C11 C12 C17 C16 177.5(11) . . . . ? C13 C12 C17 C16 5(2) . . . . ? C15 C16 C17 C12 -3(2) . . . . ? N12 N11 C18 N13 1.6(15) . . . . ? Cu1 N11 C18 N13 171.4(8) . . . . ? C19 N13 C18 N11 -0.8(14) . . . . ? N14 N13 C18 N11 179.6(11) . . . . ? N14 N13 C19 N12 179.4(11) . . . . ? C18 N13 C19 N12 -0.1(17) . . . . ? N11 N12 C19 N13 0.9(15) . . . . ? _refine_diff_density_max 0.253 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.058 #===== end # start Validation Reply Form _vrf_PLAT026_1 ; PROBLEM: Ratio Observed / Unique Reflections too Low .... 13 % RESPONSE: weak diffraction ; _vrf_PLAT029_1 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.795 RESPONSE: weak diffraction ; _vrf_PLAT201_1 ; PROBLEM: Isotropic non-H Atoms in Main Residue(s) ....... 26 RESPONSE: Because of too low data completeness and too low ratio of observed/unique reflections, in 1 non-hydrogen (except Cu and Cl) atoms were refined with isotropic displacement parameters ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 949088'