# Supplementary Material (ESI) for Metallomics # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Metallomics #============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_coden_cambridge 1400 #TrackingRef 'WYp1-updated.cif' #============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Dr. Peter Peng Foo Lee Natural Sciences and Science Education, NIE Nanyang Technological University 1 Nanyang Walk SINGAPORE 637 616 ; _publ_contact_author_phone '(65) 6790 3844' _publ_contact_author_fax '(65) 6896 9414' _publ_contact_author_email peter.lee@nie.edu.sg _publ_requested_coeditor_name ' ' _publ_contact_letter ; ; #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Cytotoxic Copper(II) Salicylaldehyde Semicarbazone Complexes: Mode of Action and Proteomic Analysis ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address #<--'Last name, first name' W.Y.Lee ; Natural Sciences and Science Education, NIE Nanyang Technological University 1 Nanyang Walk SINGAPORE 637 616 ; P.P.F.Lee ; Natural Sciences and Science Education, NIE Nanyang Technological University 1 Nanyang Walk SINGAPORE 637 616 ; Y.K.Yan ; Natural Sciences and Science Education, NIE Nanyang Technological University 1 Nanyang Walk SINGAPORE 637 616 ; M.Lau ; School of Chemical and Life Sciences Nanyang Polytechnic 180 Ang Mo Kio Avenue 8 SINGAPORE 569 830 ; _publ_contact_author_name 'Dr. Peter Peng Foo Lee' #============================================================================== data_wy160909 _database_code_depnum_ccdc_archive 'CCDC 777767' #TrackingRef 'WYp1-updated.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H52 Cl2 Cu2 N6 O5' _chemical_formula_weight 810.79 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.830(2) _cell_length_b 12.567(1) _cell_length_c 13.948(5) _cell_angle_alpha 90.41(2) _cell_angle_beta 107.95(2) _cell_angle_gamma 96.696(8) _cell_volume 1957.1(7) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5.21 _cell_measurement_theta_max 12.59 _exptl_crystal_description Rectangular _exptl_crystal_colour Brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 1.268 _exptl_absorpt_correction_type 'empirical from psi scans' _exptl_absorpt_correction_T_min 0.5141 _exptl_absorpt_correction_T_max 0.5610 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7960 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6869 _reflns_number_gt 5641 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL non-zero reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The C15'-C16' distance was restrained to be 1.540 +- 0.001 . Refinement without the restraint led to an unreasonably short C15'-C16' bond length of ca. 1.3 . ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+1.8000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom + difmap' _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6869 _refine_ls_number_parameters 433 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_restrained_S_all 1.136 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.60401(4) 0.80671(3) 0.13870(3) 0.03316(12) Uani 1 1 d . . . Cu2 Cu 0.64824(3) 0.95893(3) 0.31669(3) 0.03249(12) Uani 1 1 d . . . Cl1 Cl 0.73561(10) 0.72445(8) 0.25639(8) 0.0666(3) Uani 1 1 d . . . Cl2 Cl 0.55819(8) 1.14306(7) 0.29183(6) 0.0416(2) Uani 1 1 d . . . O1 O 0.6777(2) 0.95191(17) 0.18539(15) 0.0357(5) Uani 1 1 d . . . O2 O 0.4908(2) 0.68084(17) 0.07222(15) 0.0359(5) Uani 1 1 d . . . N1 N 0.5601(2) 0.8514(2) -0.00138(18) 0.0292(5) Uani 1 1 d . . . N2 N 0.4809(2) 0.7746(2) -0.06766(19) 0.0347(6) Uani 1 1 d . . . H2A H 0.4548 0.7821 -0.1317 0.042 Uiso 1 1 calc R . . N3 N 0.3724(2) 0.6056(2) -0.07824(19) 0.0337(6) Uani 1 1 d . . . C1 C 0.6823(3) 1.0221(2) 0.0266(2) 0.0295(6) Uani 1 1 d . . . C2 C 0.7179(3) 1.0281(2) 0.1327(2) 0.0293(6) Uani 1 1 d . . . C3 C 0.7971(3) 1.1168(3) 0.1839(2) 0.0364(7) Uani 1 1 d . . . H3A H 0.8200 1.1233 0.2540 0.044 Uiso 1 1 calc R . . C4 C 0.8410(3) 1.1945(3) 0.1311(3) 0.0413(8) Uani 1 1 d . . . H4A H 0.8943 1.2523 0.1664 0.050 Uiso 1 1 calc R . . C5 C 0.8081(3) 1.1887(3) 0.0271(3) 0.0405(8) Uani 1 1 d . . . H5A H 0.8393 1.2416 -0.0073 0.049 Uiso 1 1 calc R . . C6 C 0.7286(3) 1.1039(3) -0.0247(2) 0.0361(7) Uani 1 1 d . . . H6A H 0.7048 1.1002 -0.0948 0.043 Uiso 1 1 calc R . . C7 C 0.5987(3) 0.9373(2) -0.0364(2) 0.0318(7) Uani 1 1 d . . . H7A H 0.5717 0.9455 -0.1057 0.038 Uiso 1 1 calc R . . C8 C 0.4477(3) 0.6856(2) -0.0222(2) 0.0302(7) Uani 1 1 d . . . C9 C 0.3260(3) 0.6041(3) -0.1892(2) 0.0386(8) Uani 1 1 d . . . H9A H 0.3159 0.6768 -0.2102 0.046 Uiso 1 1 calc R . . H9B H 0.2477 0.5619 -0.2115 0.046 Uiso 1 1 calc R . . C10 C 0.4068(4) 0.5585(3) -0.2401(3) 0.0471(9) Uani 1 1 d . . . H10A H 0.4274 0.4905 -0.2115 0.056 Uiso 1 1 calc R . . H10B H 0.4803 0.6071 -0.2272 0.056 Uiso 1 1 calc R . . C11 C 0.3474(5) 0.5414(4) -0.3529(3) 0.0634(12) Uani 1 1 d . . . H11A H 0.2720 0.4957 -0.3654 0.076 Uiso 1 1 calc R . . H11B H 0.3300 0.6100 -0.3816 0.076 Uiso 1 1 calc R . . C12 C 0.4233(7) 0.4914(5) -0.4051(4) 0.109(2) Uani 1 1 d . . . H12A H 0.3810 0.4815 -0.4760 0.164 Uiso 1 1 calc R . . H12B H 0.4404 0.4231 -0.3776 0.164 Uiso 1 1 calc R . . H12C H 0.4970 0.5375 -0.3952 0.164 Uiso 1 1 calc R . . C13 C 0.3435(3) 0.5073(2) -0.0290(3) 0.0379(8) Uani 1 1 d . . . H13A H 0.4089 0.5013 0.0322 0.046 Uiso 1 1 calc R . . H13B H 0.3377 0.4459 -0.0734 0.046 Uiso 1 1 calc R . . C14 C 0.2295(4) 0.5030(3) -0.0026(3) 0.0526(10) Uani 1 1 d . . . H14A H 0.1625 0.5030 -0.0638 0.063 Uiso 1 1 calc R . . H14B H 0.2324 0.5662 0.0388 0.063 Uiso 1 1 calc R . . C15 C 0.2109(4) 0.4034(4) 0.0541(4) 0.0773(15) Uani 1 1 d . . . H15A H 0.2121 0.3410 0.0132 0.093 Uiso 1 1 calc R . . H15B H 0.2777 0.4051 0.1157 0.093 Uiso 1 1 calc R . . C16 C 0.0972(5) 0.3898(5) 0.0810(5) 0.100(2) Uani 1 1 d . . . H16A H 0.0929 0.3251 0.1165 0.149 Uiso 1 1 calc R . . H16B H 0.0300 0.3857 0.0205 0.149 Uiso 1 1 calc R . . H16C H 0.0957 0.4500 0.1232 0.149 Uiso 1 1 calc R . . O1' O 0.5096(2) 0.86012(18) 0.25066(15) 0.0387(5) Uani 1 1 d . . . O2' O 0.8035(2) 1.03409(19) 0.40078(15) 0.0384(5) Uani 1 1 d . . . N1' N 0.6308(2) 0.9358(2) 0.44933(18) 0.0346(6) Uani 1 1 d . . . N2' N 0.7201(3) 0.9965(2) 0.52435(19) 0.0416(7) Uani 1 1 d . . . H2'A H 0.7192 1.0021 0.5856 0.050 Uiso 1 1 calc R . . N3' N 0.9003(3) 1.1079(2) 0.5574(2) 0.0419(7) Uani 1 1 d . . . C1' C 0.4540(3) 0.8085(3) 0.3990(2) 0.0356(7) Uani 1 1 d . . . C2' C 0.4412(3) 0.8003(3) 0.2946(2) 0.0344(7) Uani 1 1 d . . . C3' C 0.3507(3) 0.7239(3) 0.2348(3) 0.0436(8) Uani 1 1 d . . . H3'A H 0.3418 0.7153 0.1665 0.052 Uiso 1 1 calc R . . C4' C 0.2743(4) 0.6608(3) 0.2751(3) 0.0534(10) Uani 1 1 d . . . H4'A H 0.2141 0.6116 0.2333 0.064 Uiso 1 1 calc R . . C5' C 0.2863(4) 0.6701(3) 0.3775(3) 0.0552(10) Uani 1 1 d . . . H5'A H 0.2349 0.6273 0.4042 0.066 Uiso 1 1 calc R . . C6' C 0.3740(3) 0.7426(3) 0.4376(3) 0.0481(9) Uani 1 1 d . . . H6'A H 0.3819 0.7492 0.5059 0.058 Uiso 1 1 calc R . . C7' C 0.5479(3) 0.8767(3) 0.4713(2) 0.0387(8) Uani 1 1 d . . . H7'A H 0.5482 0.8779 0.5381 0.046 Uiso 1 1 calc R . . C8' C 0.8097(3) 1.0467(3) 0.4922(2) 0.0359(7) Uani 1 1 d . . . C9' C 0.9978(3) 1.1576(3) 0.5209(3) 0.0491(9) Uani 1 1 d . . . H9'A H 1.0083 1.1093 0.4706 0.059 Uiso 1 1 calc R . . H9'B H 1.0717 1.1671 0.5768 0.059 Uiso 1 1 calc R . . C10' C 0.9746(4) 1.2643(4) 0.4757(4) 0.0713(13) Uani 1 1 d . . . H10C H 0.9707 1.3148 0.5271 0.086 Uiso 1 1 calc R . . H10D H 0.8981 1.2563 0.4226 0.086 Uiso 1 1 calc R . . C11' C 1.0734(7) 1.3077(5) 0.4323(6) 0.115(2) Uani 1 1 d . . . H11C H 1.1492 1.3149 0.4860 0.138 Uiso 1 1 calc R . . H11D H 1.0777 1.2555 0.3823 0.138 Uiso 1 1 calc R . . C12' C 1.0580(9) 1.4120(6) 0.3850(6) 0.165(4) Uani 1 1 d . . . H12D H 1.1235 1.4332 0.3595 0.248 Uiso 1 1 calc R . . H12E H 1.0564 1.4650 0.4342 0.248 Uiso 1 1 calc R . . H12F H 0.9841 1.4055 0.3305 0.248 Uiso 1 1 calc R . . C13' C 0.9085(4) 1.1313(4) 0.6627(3) 0.0583(11) Uani 1 1 d . . . H13C H 0.8284 1.1241 0.6685 0.070 Uiso 1 1 calc R . . H13D H 0.9437 1.2051 0.6811 0.070 Uiso 1 1 calc R . . C14' C 0.9823(4) 1.0588(5) 0.7360(3) 0.0863(18) Uani 1 1 d . . . H14C H 0.9584 0.9863 0.7068 0.104 Uiso 1 1 calc R . . H14D H 1.0650 1.0780 0.7386 0.104 Uiso 1 1 calc R . . C15' C 0.9800(6) 1.0555(7) 0.8411(4) 0.177(5) Uani 1 1 d D . . H15C H 1.0098 0.9905 0.8703 0.212 Uiso 1 1 calc R . . H15D H 0.8981 1.0538 0.8418 0.212 Uiso 1 1 calc R . . C16' C 1.0569(7) 1.1535(7) 0.9049(6) 0.164(4) Uani 1 1 d D . . H16D H 1.0422 1.1566 0.9687 0.246 Uiso 1 1 calc R . . H16E H 1.0366 1.2176 0.8700 0.246 Uiso 1 1 calc R . . H16F H 1.1401 1.1476 0.9157 0.246 Uiso 1 1 calc R . . O1S O 0.2970(3) 1.0678(3) 0.2821(2) 0.0801(10) Uani 1 1 d . . . H2S H 0.3678 1.0717 0.2851 0.096 Uiso 1 1 calc R . . C1S C 0.2499(6) 1.1594(7) 0.2391(6) 0.133(3) Uani 1 1 d . . . H1SA H 0.2983 1.2221 0.2761 0.160 Uiso 1 1 calc R . . H1SB H 0.1695 1.1581 0.2414 0.160 Uiso 1 1 calc R . . H1SC H 0.2496 1.1611 0.1702 0.160 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0428(2) 0.0295(2) 0.02228(19) 0.00013(14) 0.00660(16) -0.00541(16) Cu2 0.0364(2) 0.0373(2) 0.01941(19) -0.00129(15) 0.00656(15) -0.00700(16) Cl1 0.0615(6) 0.0512(6) 0.0604(6) 0.0170(5) -0.0160(5) -0.0047(5) Cl2 0.0535(5) 0.0409(5) 0.0293(4) 0.0030(3) 0.0119(4) 0.0035(4) O1 0.0485(13) 0.0333(12) 0.0235(10) -0.0017(9) 0.0138(10) -0.0093(10) O2 0.0467(13) 0.0310(11) 0.0258(11) -0.0006(9) 0.0093(10) -0.0063(10) N1 0.0310(13) 0.0290(13) 0.0244(12) -0.0020(10) 0.0063(10) -0.0030(11) N2 0.0414(15) 0.0329(14) 0.0228(12) -0.0011(11) 0.0045(11) -0.0080(12) N3 0.0380(15) 0.0291(14) 0.0292(13) -0.0035(11) 0.0074(11) -0.0059(11) C1 0.0294(16) 0.0313(16) 0.0280(15) 0.0028(12) 0.0104(12) 0.0003(13) C2 0.0292(16) 0.0297(16) 0.0298(15) -0.0011(12) 0.0115(13) 0.0013(12) C3 0.0383(18) 0.0376(18) 0.0299(16) -0.0032(13) 0.0096(14) -0.0058(14) C4 0.0404(19) 0.0332(18) 0.046(2) -0.0048(15) 0.0130(16) -0.0114(15) C5 0.046(2) 0.0335(18) 0.0416(19) 0.0058(14) 0.0171(16) -0.0076(15) C6 0.0403(18) 0.0367(18) 0.0297(16) 0.0044(13) 0.0111(14) -0.0029(14) C7 0.0363(17) 0.0337(17) 0.0234(14) 0.0021(12) 0.0081(13) -0.0007(13) C8 0.0311(16) 0.0305(16) 0.0290(16) -0.0013(12) 0.0107(13) 0.0000(13) C9 0.0413(19) 0.0365(18) 0.0300(16) -0.0035(13) 0.0040(14) -0.0068(14) C10 0.061(2) 0.042(2) 0.041(2) 0.0005(16) 0.0205(18) 0.0038(17) C11 0.099(4) 0.061(3) 0.035(2) 0.0037(18) 0.024(2) 0.016(2) C12 0.163(6) 0.128(5) 0.060(3) 0.005(3) 0.057(4) 0.054(5) C13 0.0438(19) 0.0263(16) 0.0401(18) -0.0020(13) 0.0116(15) -0.0058(14) C14 0.052(2) 0.039(2) 0.069(3) 0.0011(18) 0.025(2) -0.0051(17) C15 0.064(3) 0.064(3) 0.115(4) 0.026(3) 0.046(3) -0.002(2) C16 0.092(4) 0.081(4) 0.144(6) 0.019(4) 0.071(4) -0.013(3) O1' 0.0439(13) 0.0440(13) 0.0236(11) -0.0028(9) 0.0112(10) -0.0148(10) O2' 0.0381(12) 0.0487(14) 0.0228(11) -0.0011(9) 0.0058(9) -0.0068(10) N1' 0.0397(15) 0.0381(15) 0.0220(12) -0.0013(11) 0.0064(11) -0.0014(12) N2' 0.0453(17) 0.0522(18) 0.0204(13) -0.0072(12) 0.0067(12) -0.0113(14) N3' 0.0389(16) 0.0507(17) 0.0283(14) -0.0077(12) 0.0027(12) -0.0043(13) C1' 0.0390(18) 0.0385(18) 0.0290(16) 0.0016(13) 0.0125(14) -0.0015(14) C2' 0.0384(18) 0.0346(17) 0.0300(16) 0.0044(13) 0.0123(14) -0.0002(14) C3' 0.050(2) 0.044(2) 0.0322(17) -0.0034(15) 0.0113(16) -0.0078(16) C4' 0.050(2) 0.055(2) 0.049(2) -0.0039(18) 0.0157(18) -0.0198(18) C5' 0.060(2) 0.054(2) 0.052(2) 0.0013(18) 0.027(2) -0.0185(19) C6' 0.059(2) 0.052(2) 0.0348(18) 0.0031(16) 0.0223(17) -0.0100(18) C7' 0.046(2) 0.0449(19) 0.0234(15) 0.0011(14) 0.0121(14) -0.0032(16) C8' 0.0369(18) 0.0353(17) 0.0304(17) 0.0004(13) 0.0044(14) 0.0011(14) C9' 0.0365(19) 0.058(2) 0.043(2) -0.0080(17) 0.0046(16) -0.0096(17) C10' 0.073(3) 0.064(3) 0.072(3) -0.001(2) 0.023(3) -0.014(2) C11' 0.125(5) 0.095(5) 0.123(5) 0.021(4) 0.050(4) -0.030(4) C12' 0.236(11) 0.108(6) 0.141(7) 0.020(5) 0.071(7) -0.058(6) C13' 0.047(2) 0.080(3) 0.040(2) -0.025(2) 0.0090(18) -0.009(2) C14' 0.045(2) 0.174(6) 0.033(2) 0.015(3) 0.0032(19) 0.005(3) C15' 0.073(4) 0.398(15) 0.042(3) -0.010(5) 0.014(3) -0.028(6) C16' 0.104(5) 0.255(11) 0.128(6) -0.118(7) 0.047(5) -0.021(6) O1S 0.0564(18) 0.133(3) 0.0465(17) 0.0222(18) 0.0144(14) -0.0036(19) C1S 0.097(5) 0.164(7) 0.152(7) 0.068(6) 0.051(5) 0.031(5) _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 O1 1.943(2) . ? Cu1 N1 1.965(2) . ? Cu1 O2 1.968(2) . ? Cu1 Cl1 2.238(1) . ? Cu1 O1' 2.318(2) . ? Cu1 Cu2 2.9991(9) . ? Cu2 O1' 1.913(2) . ? Cu2 N1' 1.944(3) . ? Cu2 O1 1.970(2) . ? Cu2 O2' 1.973(2) . ? Cu2 Cl2 2.640(1) . ? O1 C2 1.342(4) . ? O2 C8 1.262(4) . ? N1 C7 1.282(4) . ? N1 N2 1.381(3) . ? N2 C8 1.367(4) . ? N3 C8 1.329(4) . ? N3 C9 1.473(4) . ? N3 C13 1.474(4) . ? C1 C2 1.408(4) . ? C1 C6 1.410(4) . ? C1 C7 1.446(4) . ? C2 C3 1.401(4) . ? C3 C4 1.376(5) . ? C4 C5 1.380(5) . ? C5 C6 1.371(5) . ? C9 C10 1.513(5) . ? C10 C11 1.514(5) . ? C11 C12 1.503(7) . ? C13 C14 1.498(5) . ? C14 C15 1.515(6) . ? C15 C16 1.496(7) . ? O1' C2' 1.329(4) . ? O2' C8' 1.262(4) . ? N1' C7' 1.276(4) . ? N1' N2' 1.382(4) . ? N2' C8' 1.365(4) . ? N3' C8' 1.328(4) . ? N3' C13' 1.468(4) . ? N3' C9' 1.475(5) . ? C1' C6' 1.417(5) . ? C1' C2' 1.418(4) . ? C1' C7' 1.435(5) . ? C2' C3' 1.401(5) . ? C3' C4' 1.382(5) . ? C4' C5' 1.394(5) . ? C5' C6' 1.357(5) . ? C9' C10' 1.504(6) . ? C10' C11' 1.523(8) . ? C11' C12' 1.48(1) . ? C13' C14' 1.511(7) . ? C14' C15' 1.475(7) . ? C15' C16' 1.537(1) . ? O1S C1S 1.396(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N1 89.92(9) . . ? O1 Cu1 O2 163.9(1) . . ? N1 Cu1 O2 80.51(9) . . ? O1 Cu1 Cl1 96.03(7) . . ? N1 Cu1 Cl1 144.52(9) . . ? O2 Cu1 Cl1 99.29(7) . . ? O1 Cu1 O1' 74.30(8) . . ? N1 Cu1 O1' 121.8(1) . . ? O2 Cu1 O1' 99.70(8) . . ? Cl1 Cu1 O1' 93.39(7) . . ? O1 Cu1 Cu2 40.30(6) . . ? N1 Cu1 Cu2 123.32(8) . . ? O2 Cu1 Cu2 138.47(7) . . ? Cl1 Cu1 Cu2 79.98(4) . . ? O1' Cu1 Cu2 39.62(5) . . ? O1' Cu2 N1' 93.1(1) . . ? O1' Cu2 O1 83.68(9) . . ? N1' Cu2 O1 167.8(1) . . ? O1' Cu2 O2' 167.8(1) . . ? N1' Cu2 O2' 80.7(1) . . ? O1 Cu2 O2' 100.18(9) . . ? O1' Cu2 Cl2 101.24(8) . . ? N1' Cu2 Cl2 95.82(9) . . ? O1 Cu2 Cl2 96.40(7) . . ? O2' Cu2 Cl2 89.91(8) . . ? O1' Cu2 Cu1 50.60(7) . . ? N1' Cu2 Cu1 131.11(8) . . ? O1 Cu2 Cu1 39.64(6) . . ? O2' Cu2 Cu1 127.28(7) . . ? Cl2 Cu2 Cu1 119.84(3) . . ? C2 O1 Cu1 127.6(2) . . ? C2 O1 Cu2 131.5(2) . . ? Cu1 O1 Cu2 100.06(9) . . ? C8 O2 Cu1 114.3(2) . . ? C7 N1 N2 118.9(2) . . ? C7 N1 Cu1 128.6(2) . . ? N2 N1 Cu1 112.4(2) . . ? C8 N2 N1 113.9(2) . . ? C8 N3 C9 123.6(3) . . ? C8 N3 C13 118.8(3) . . ? C9 N3 C13 117.2(2) . . ? C2 C1 C6 119.4(3) . . ? C2 C1 C7 124.7(3) . . ? C6 C1 C7 115.9(3) . . ? O1 C2 C3 119.6(3) . . ? O1 C2 C1 121.9(3) . . ? C3 C2 C1 118.5(3) . . ? C4 C3 C2 120.3(3) . . ? C3 C4 C5 121.7(3) . . ? C6 C5 C4 119.0(3) . . ? C5 C6 C1 121.1(3) . . ? N1 C7 C1 123.2(3) . . ? O2 C8 N3 121.5(3) . . ? O2 C8 N2 119.0(3) . . ? N3 C8 N2 119.5(3) . . ? N3 C9 C10 113.2(3) . . ? C9 C10 C11 111.7(3) . . ? C12 C11 C10 113.1(4) . . ? N3 C13 C14 114.4(3) . . ? C13 C14 C15 111.0(3) . . ? C16 C15 C14 115.2(4) . . ? C2' O1' Cu2 126.6(2) . . ? C2' O1' Cu1 128.8(2) . . ? Cu2 O1' Cu1 89.78(9) . . ? C8' O2' Cu2 113.1(2) . . ? C7' N1' N2' 120.0(3) . . ? C7' N1' Cu2 127.9(2) . . ? N2' N1' Cu2 112.0(2) . . ? C8' N2' N1' 113.8(2) . . ? C8' N3' C13' 124.3(3) . . ? C8' N3' C9' 117.9(3) . . ? C13' N3' C9' 117.8(3) . . ? C6' C1' C2' 119.5(3) . . ? C6' C1' C7' 116.4(3) . . ? C2' C1' C7' 124.1(3) . . ? O1' C2' C3' 118.4(3) . . ? O1' C2' C1' 124.1(3) . . ? C3' C2' C1' 117.5(3) . . ? C4' C3' C2' 121.5(3) . . ? C3' C4' C5' 120.8(3) . . ? C6' C5' C4' 119.1(3) . . ? C5' C6' C1' 121.7(3) . . ? N1' C7' C1' 123.9(3) . . ? O2' C8' N3' 121.8(3) . . ? O2' C8' N2' 118.8(3) . . ? N3' C8' N2' 119.4(3) . . ? N3' C9' C10' 113.1(3) . . ? C9' C10' C11' 110.8(5) . . ? C12' C11' C10' 114.9(7) . . ? N3' C13' C14' 113.4(4) . . ? C15' C14' C13' 120.7(6) . . ? C14' C15' C16' 111.2(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.193 _refine_diff_density_min -0.956 _refine_diff_density_rms 0.076 #=====END