# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_mo_am_073_sb_014_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H56 Cu N12 O6, 2(ClO4)' _chemical_formula_sum 'C38 H56 Cl2 Cu N12 O14' _chemical_formula_weight 1039.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 39.869(4) _cell_length_b 13.5647(12) _cell_length_c 20.4661(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.536(2) _cell_angle_gamma 90.00 _cell_volume 11067.9(17) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9816 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 28.18 _exptl_crystal_description 'block shaped' _exptl_crystal_colour blue _exptl_crystal_size_max 0.456 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5016 _exptl_absorpt_coefficient_mu 0.557 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6710 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details (SADABS,Sheldrick,bruker,2001) _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 91296 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -50 _diffrn_reflns_limit_h_max 50 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.02 _diffrn_reflns_theta_max 27.00 _reflns_number_total 12090 _reflns_number_gt 10299 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+22.0133P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12090 _refine_ls_number_parameters 614 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1213 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 1.0000 0.5000 0.5000 0.01997(10) Uani 1 2 d S . . O1 O 0.94441(4) 0.54725(12) 0.48525(9) 0.0256(4) Uani 1 1 d . . . O2 O 0.85195(4) 0.47273(11) 0.62473(8) 0.0230(3) Uani 1 1 d . . . O3 O 0.88152(4) 0.58310(11) 0.68727(7) 0.0186(3) Uani 1 1 d . . . N1 N 0.98196(4) 0.40665(14) 0.56858(10) 0.0220(4) Uani 1 1 d . . . N2 N 0.95275(4) 0.35680(13) 0.55491(9) 0.0190(4) Uani 1 1 d . . . N3 N 0.98845(4) 0.39434(14) 0.43377(10) 0.0225(4) Uani 1 1 d . . . N4 N 0.95834(4) 0.34565(13) 0.43963(9) 0.0186(4) Uani 1 1 d . . . N5 N 0.89076(4) 0.48938(13) 0.47848(9) 0.0174(4) Uani 1 1 d . . . N6 N 0.86803(5) 0.62289(13) 0.58608(8) 0.0188(4) Uani 1 1 d . . . C1 C 0.99308(5) 0.36964(17) 0.62534(11) 0.0221(4) Uani 1 1 d . . . C2 C 0.97109(6) 0.29629(18) 0.64732(12) 0.0251(5) Uani 1 1 d . . . H2 H 0.9732 0.2597 0.6856 0.030 Uiso 1 1 calc R . . C3 C 0.94590(6) 0.28902(17) 0.60159(11) 0.0230(5) Uani 1 1 d . . . C4 C 1.02431(6) 0.4057(2) 0.65852(13) 0.0303(5) Uani 1 1 d . . . H4A H 1.0416 0.4146 0.6267 0.046 Uiso 1 1 calc R . . H4B H 1.0315 0.3583 0.6905 0.046 Uiso 1 1 calc R . . H4C H 1.0198 0.4674 0.6797 0.046 Uiso 1 1 calc R . . C5 C 0.91547(7) 0.2247(2) 0.59865(13) 0.0386(7) Uani 1 1 d . . . H5A H 0.8959 0.2649 0.5925 0.058 Uiso 1 1 calc R . . H5B H 0.9136 0.1885 0.6388 0.058 Uiso 1 1 calc R . . H5C H 0.9174 0.1795 0.5628 0.058 Uiso 1 1 calc R . . C6 C 1.00434(6) 0.34885(18) 0.38501(12) 0.0253(5) Uani 1 1 d . . . C7 C 0.98454(6) 0.27214(17) 0.36006(12) 0.0252(5) Uani 1 1 d . . . H7 H 0.9900 0.2304 0.3257 0.030 Uiso 1 1 calc R . . C8 C 0.95565(5) 0.27017(16) 0.39587(11) 0.0211(4) Uani 1 1 d . . . C9 C 1.03825(6) 0.3808(2) 0.36249(14) 0.0351(6) Uani 1 1 d . . . H9A H 1.0358 0.4313 0.3299 0.053 Uiso 1 1 calc R . . H9B H 1.0498 0.3255 0.3441 0.053 Uiso 1 1 calc R . . H9C H 1.0509 0.4062 0.3989 0.053 Uiso 1 1 calc R . . C10 C 0.92685(6) 0.20062(17) 0.39363(13) 0.0276(5) Uani 1 1 d . . . H10A H 0.9276 0.1588 0.4315 0.041 Uiso 1 1 calc R . . H10B H 0.9282 0.1609 0.3549 0.041 Uiso 1 1 calc R . . H10C H 0.9062 0.2372 0.3931 0.041 Uiso 1 1 calc R . . C11 C 0.93592(5) 0.37151(16) 0.49258(10) 0.0181(4) Uani 1 1 d . . . H11 H 0.9164 0.3279 0.4905 0.022 Uiso 1 1 calc R . . C12 C 0.92377(5) 0.47873(16) 0.48521(10) 0.0178(4) Uani 1 1 d . . . C13 C 0.87485(5) 0.58557(16) 0.46819(10) 0.0194(4) Uani 1 1 d . . . H13A H 0.8625 0.5846 0.4272 0.023 Uiso 1 1 calc R . . H13B H 0.8921 0.6357 0.4650 0.023 Uiso 1 1 calc R . . C14 C 0.85103(5) 0.61266(16) 0.52330(10) 0.0187(4) Uani 1 1 d . . . H14A H 0.8399 0.6743 0.5126 0.022 Uiso 1 1 calc R . . H14B H 0.8339 0.5621 0.5267 0.022 Uiso 1 1 calc R . . C15 C 0.86599(5) 0.55145(16) 0.63207(10) 0.0170(4) Uani 1 1 d . . . C16 C 0.88609(5) 0.51651(16) 0.74346(10) 0.0187(4) Uani 1 1 d . . . C17 C 0.90491(6) 0.58166(19) 0.79204(11) 0.0266(5) Uani 1 1 d . . . H17A H 0.9258 0.6021 0.7735 0.040 Uiso 1 1 calc R . . H17B H 0.9092 0.5453 0.8315 0.040 Uiso 1 1 calc R . . H17C H 0.8916 0.6387 0.8018 0.040 Uiso 1 1 calc R . . C18 C 0.85248(5) 0.48644(18) 0.77113(11) 0.0226(5) Uani 1 1 d . . . H18A H 0.8399 0.5443 0.7824 0.034 Uiso 1 1 calc R . . H18B H 0.8560 0.4469 0.8095 0.034 Uiso 1 1 calc R . . H18C H 0.8402 0.4490 0.7391 0.034 Uiso 1 1 calc R . . C19 C 0.90662(6) 0.42727(17) 0.72449(12) 0.0253(5) Uani 1 1 d . . . H19A H 0.8942 0.3883 0.6935 0.038 Uiso 1 1 calc R . . H19B H 0.9114 0.3885 0.7627 0.038 Uiso 1 1 calc R . . H19C H 0.9273 0.4485 0.7053 0.038 Uiso 1 1 calc R . . Cl1 Cl 0.92438(2) 0.14495(8) 0.81714(4) 0.0633(3) Uani 1 1 d . . . O7 O 0.95679(8) 0.1754(3) 0.79793(17) 0.0941(11) Uani 1 1 d . . . O8 O 0.90620(12) 0.1269(5) 0.7581(2) 0.162(2) Uani 1 1 d . . . O9 O 0.92533(9) 0.0594(3) 0.85418(18) 0.0987(12) Uani 1 1 d . . . O10 O 0.90735(12) 0.2227(3) 0.8510(2) 0.1168(14) Uani 1 1 d . . . Cu2 Cu 0.2500 0.7500 0.0000 0.01115(9) Uani 1 2 d S . . O4 O 0.20168(3) 0.82574(10) 0.03357(7) 0.0158(3) Uani 1 1 d . . . O5 O 0.16847(4) 1.15994(12) -0.05138(8) 0.0241(3) Uani 1 1 d . . . O6 O 0.16290(4) 1.06864(11) -0.14429(8) 0.0245(3) Uani 1 1 d . . . N7 N 0.27069(4) 0.80401(11) 0.08261(8) 0.0126(3) Uani 1 1 d . . . N8 N 0.26061(4) 0.89619(12) 0.10199(8) 0.0125(3) Uani 1 1 d . . . N9 N 0.23852(4) 0.62038(12) 0.04182(8) 0.0144(3) Uani 1 1 d . . . N10 N 0.25770(4) 0.96302(12) -0.00487(8) 0.0128(3) Uani 1 1 d . . . N11 N 0.18082(4) 0.97676(12) 0.05942(9) 0.0160(3) Uani 1 1 d . . . N12 N 0.13696(5) 1.01938(14) -0.05539(10) 0.0230(4) Uani 1 1 d . . . C20 C 0.29108(5) 0.77145(15) 0.12985(10) 0.0154(4) Uani 1 1 d . . . C21 C 0.29399(5) 0.84237(15) 0.17942(10) 0.0172(4) Uani 1 1 d . . . H21 H 0.3065 0.8368 0.2178 0.021 Uiso 1 1 calc R . . C22 C 0.27480(5) 0.92163(15) 0.16048(10) 0.0148(4) Uani 1 1 d . . . C23 C 0.30787(6) 0.67316(15) 0.12641(11) 0.0217(4) Uani 1 1 d . . . H23A H 0.2922 0.6226 0.1381 0.033 Uiso 1 1 calc R . . H23B H 0.3266 0.6719 0.1562 0.033 Uiso 1 1 calc R . . H23C H 0.3156 0.6619 0.0827 0.033 Uiso 1 1 calc R . . C24 C 0.26906(6) 1.01932(16) 0.19198(11) 0.0211(4) Uani 1 1 d . . . H24A H 0.2822 1.0687 0.1703 0.032 Uiso 1 1 calc R . . H24B H 0.2756 1.0160 0.2372 0.032 Uiso 1 1 calc R . . H24C H 0.2457 1.0361 0.1887 0.032 Uiso 1 1 calc R . . C25 C 0.22020(5) 0.59309(15) 0.09312(10) 0.0157(4) Uani 1 1 d . . . C26 C 0.28801(5) 1.00734(15) -0.08825(11) 0.0183(4) Uani 1 1 d . . . H26 H 0.3006 1.0438 -0.1177 0.022 Uiso 1 1 calc R . . C27 C 0.27390(5) 1.04127(14) -0.03139(11) 0.0166(4) Uani 1 1 d . . . C28 C 0.21109(6) 0.66399(16) 0.14586(11) 0.0236(5) Uani 1 1 d . . . H28A H 0.2309 0.6817 0.1702 0.035 Uiso 1 1 calc R . . H28B H 0.1952 0.6338 0.1745 0.035 Uiso 1 1 calc R . . H28C H 0.2014 0.7221 0.1267 0.035 Uiso 1 1 calc R . . C29 C 0.27479(6) 1.13968(15) 0.00051(13) 0.0279(5) Uani 1 1 d . . . H29A H 0.2526 1.1572 0.0143 0.042 Uiso 1 1 calc R . . H29B H 0.2828 1.1879 -0.0300 0.042 Uiso 1 1 calc R . . H29C H 0.2895 1.1375 0.0378 0.042 Uiso 1 1 calc R . . C30 C 0.24100(5) 0.95674(14) 0.05752(9) 0.0124(4) Uani 1 1 d . . . H30 H 0.2392 1.0232 0.0759 0.015 Uiso 1 1 calc R . . C31 C 0.20535(5) 0.91337(14) 0.04885(9) 0.0122(4) Uani 1 1 d . . . C32 C 0.14519(5) 0.94967(16) 0.05555(11) 0.0197(4) Uani 1 1 d . . . H32A H 0.1357 0.9500 0.0990 0.024 Uiso 1 1 calc R . . H32B H 0.1430 0.8836 0.0379 0.024 Uiso 1 1 calc R . . C33 C 0.12613(5) 1.02197(16) 0.01211(11) 0.0217(4) Uani 1 1 d . . . H33A H 0.1024 1.0068 0.0137 0.026 Uiso 1 1 calc R . . H33B H 0.1292 1.0881 0.0291 0.026 Uiso 1 1 calc R . . C34 C 0.15723(5) 1.08885(16) -0.08136(11) 0.0202(4) Uani 1 1 d . . . C35 C 0.18361(6) 1.13416(16) -0.18509(11) 0.0239(5) Uani 1 1 d . . . C36 C 0.21906(7) 1.1368(2) -0.15896(15) 0.0395(6) Uani 1 1 d . . . H36A H 0.2194 1.1684 -0.1170 0.059 Uiso 1 1 calc R . . H36B H 0.2330 1.1731 -0.1885 0.059 Uiso 1 1 calc R . . H36C H 0.2274 1.0708 -0.1547 0.059 Uiso 1 1 calc R . . C37 C 0.16785(8) 1.23599(18) -0.19015(13) 0.0351(6) Uani 1 1 d . . . H37A H 0.1450 1.2299 -0.2047 0.053 Uiso 1 1 calc R . . H37B H 0.1801 1.2751 -0.2209 0.053 Uiso 1 1 calc R . . H37C H 0.1685 1.2673 -0.1481 0.053 Uiso 1 1 calc R . . C38 C 0.18232(7) 1.0823(2) -0.25122(13) 0.0343(6) Uani 1 1 d . . . H38A H 0.1914 1.0170 -0.2469 0.051 Uiso 1 1 calc R . . H38B H 0.1953 1.1189 -0.2822 0.051 Uiso 1 1 calc R . . H38C H 0.1595 1.0784 -0.2662 0.051 Uiso 1 1 calc R . . Cl2 Cl 0.186996(13) 0.80811(3) 0.65961(2) 0.01915(11) Uani 1 1 d . . . O11 O 0.17838(5) 0.70497(11) 0.65461(8) 0.0287(4) Uani 1 1 d . . . O13 O 0.15708(5) 0.86669(15) 0.65521(10) 0.0393(4) Uiso 1 1 d . . . O16 O 0.2043(2) 0.8274(6) 0.7201(3) 0.0111(16) Uiso 0.40 1 d P . . O14 O 0.1968(2) 0.8332(7) 0.7202(5) 0.028(3) Uiso 0.30 1 d P . . O15 O 0.2113(2) 0.8169(6) 0.7172(4) 0.026(3) Uiso 0.30 1 d P . . O12 O 0.20851(4) 0.83449(12) 0.60555(8) 0.0235(3) 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 0.01226(17) 0.02061(19) 0.0271(2) 0.00386(15) 0.00050(14) -0.00612(13) O1 0.0157(7) 0.0206(8) 0.0404(10) 0.0042(7) 0.0004(7) -0.0061(6) O2 0.0285(8) 0.0200(8) 0.0206(8) -0.0003(6) -0.0034(6) -0.0042(6) O3 0.0222(7) 0.0194(7) 0.0141(7) 0.0019(6) -0.0014(6) -0.0049(6) N1 0.0140(8) 0.0237(9) 0.0282(10) 0.0033(8) -0.0025(7) -0.0072(7) N2 0.0110(8) 0.0219(9) 0.0241(9) 0.0033(7) -0.0010(7) -0.0051(7) N3 0.0131(8) 0.0252(10) 0.0293(10) 0.0042(8) 0.0037(7) -0.0067(7) N4 0.0116(8) 0.0191(9) 0.0252(9) 0.0026(7) 0.0029(7) -0.0042(7) N5 0.0157(8) 0.0202(9) 0.0163(8) 0.0006(7) 0.0007(7) -0.0017(7) N6 0.0212(9) 0.0221(9) 0.0130(8) 0.0026(7) 0.0000(7) -0.0018(7) C1 0.0177(10) 0.0232(11) 0.0253(11) 0.0003(9) -0.0011(8) -0.0030(8) C2 0.0220(11) 0.0295(12) 0.0236(11) 0.0052(9) -0.0013(9) -0.0062(9) C3 0.0202(11) 0.0263(11) 0.0225(11) 0.0029(9) 0.0005(8) -0.0079(9) C4 0.0226(11) 0.0358(13) 0.0325(13) 0.0051(11) -0.0067(10) -0.0075(10) C5 0.0352(14) 0.0525(17) 0.0280(13) 0.0172(12) -0.0072(11) -0.0281(13) C6 0.0194(11) 0.0276(12) 0.0289(12) 0.0047(9) 0.0049(9) -0.0031(9) C7 0.0214(11) 0.0235(11) 0.0309(13) 0.0014(9) 0.0070(9) -0.0009(9) C8 0.0173(10) 0.0178(10) 0.0283(12) 0.0030(9) 0.0026(9) 0.0000(8) C9 0.0232(12) 0.0401(14) 0.0424(15) 0.0002(12) 0.0142(11) -0.0081(11) C10 0.0230(11) 0.0224(11) 0.0377(14) -0.0046(10) 0.0063(10) -0.0072(9) C11 0.0129(9) 0.0209(10) 0.0204(10) 0.0035(8) 0.0006(8) -0.0040(8) C12 0.0152(9) 0.0211(10) 0.0170(10) 0.0006(8) 0.0017(8) -0.0036(8) C13 0.0186(10) 0.0234(11) 0.0163(10) 0.0034(8) 0.0002(8) 0.0005(8) C14 0.0165(10) 0.0227(10) 0.0167(10) 0.0021(8) -0.0018(8) 0.0010(8) C15 0.0142(9) 0.0204(10) 0.0165(10) -0.0006(8) 0.0023(7) 0.0000(8) C16 0.0188(10) 0.0222(10) 0.0150(10) 0.0043(8) -0.0001(8) -0.0028(8) C17 0.0263(12) 0.0341(13) 0.0192(11) -0.0003(9) -0.0043(9) -0.0078(10) C18 0.0191(10) 0.0305(12) 0.0183(11) 0.0056(9) 0.0023(8) -0.0026(9) C19 0.0207(11) 0.0262(11) 0.0289(12) 0.0028(9) -0.0003(9) 0.0025(9) Cl1 0.0539(5) 0.0866(7) 0.0494(5) 0.0256(5) -0.0089(4) -0.0397(5) O7 0.078(2) 0.115(3) 0.090(2) 0.028(2) 0.0124(17) -0.049(2) O8 0.117(4) 0.248(7) 0.119(4) 0.005(4) -0.056(3) -0.050(4) O9 0.105(3) 0.084(2) 0.108(3) 0.044(2) 0.047(2) -0.0039(19) O10 0.136(4) 0.086(2) 0.129(3) 0.021(2) 0.057(3) 0.007(2) Cu2 0.01462(16) 0.00822(15) 0.01063(16) 0.00006(12) 0.00163(12) -0.00094(12) O4 0.0157(7) 0.0112(6) 0.0205(7) -0.0028(5) 0.0018(6) -0.0004(5) O5 0.0260(8) 0.0215(8) 0.0248(8) -0.0048(6) 0.0003(6) -0.0002(6) O6 0.0323(9) 0.0188(8) 0.0224(8) -0.0010(6) -0.0002(7) 0.0011(6) N7 0.0157(8) 0.0082(7) 0.0140(8) 0.0006(6) 0.0017(6) 0.0010(6) N8 0.0154(8) 0.0080(7) 0.0140(8) -0.0007(6) -0.0005(6) 0.0011(6) N9 0.0194(8) 0.0106(8) 0.0132(8) -0.0008(6) 0.0027(6) -0.0008(6) N10 0.0145(8) 0.0095(7) 0.0145(8) 0.0006(6) 0.0014(6) 0.0005(6) N11 0.0130(8) 0.0124(8) 0.0227(9) 0.0003(7) 0.0022(7) 0.0016(6) N12 0.0208(9) 0.0217(9) 0.0265(10) -0.0006(8) -0.0006(8) 0.0019(7) C20 0.0153(9) 0.0153(9) 0.0156(10) 0.0019(8) 0.0002(7) 0.0005(7) C21 0.0198(10) 0.0175(10) 0.0141(9) -0.0001(8) -0.0035(8) 0.0004(8) C22 0.0145(9) 0.0169(9) 0.0131(9) -0.0003(7) -0.0002(7) -0.0019(7) C23 0.0267(11) 0.0157(10) 0.0227(11) -0.0009(8) -0.0052(9) 0.0064(8) C24 0.0239(11) 0.0181(10) 0.0212(11) -0.0060(8) -0.0045(8) 0.0024(8) C25 0.0168(9) 0.0158(9) 0.0145(9) 0.0029(8) 0.0028(7) 0.0003(7) C26 0.0207(10) 0.0131(9) 0.0212(10) 0.0052(8) 0.0074(8) 0.0009(8) C27 0.0145(9) 0.0116(9) 0.0237(11) 0.0049(8) 0.0033(8) 0.0007(7) C28 0.0358(13) 0.0178(10) 0.0173(10) -0.0006(8) 0.0110(9) -0.0038(9) C29 0.0341(13) 0.0114(10) 0.0386(14) -0.0010(9) 0.0192(11) -0.0026(9) C30 0.0137(9) 0.0111(9) 0.0126(9) -0.0001(7) 0.0006(7) 0.0012(7) C31 0.0138(9) 0.0131(9) 0.0097(9) 0.0022(7) 0.0013(7) 0.0015(7) C32 0.0133(9) 0.0170(10) 0.0289(12) 0.0007(8) 0.0025(8) 0.0015(8) C33 0.0158(10) 0.0210(10) 0.0282(12) -0.0006(9) 0.0010(8) 0.0046(8) C34 0.0174(10) 0.0192(10) 0.0241(11) 0.0008(8) -0.0025(8) 0.0073(8) C35 0.0274(12) 0.0190(10) 0.0253(12) 0.0000(9) 0.0037(9) 0.0059(9) C36 0.0263(13) 0.0528(17) 0.0395(15) -0.0056(13) 0.0028(11) 0.0019(12) C37 0.0508(16) 0.0235(12) 0.0313(14) 0.0054(10) 0.0115(12) 0.0149(11) C38 0.0467(16) 0.0294(13) 0.0268(13) -0.0044(10) 0.0063(11) 0.0055(11) Cl2 0.0291(3) 0.0117(2) 0.0167(2) -0.00019(17) 0.00494(19) -0.00265(18) O11 0.0459(10) 0.0143(8) 0.0261(9) -0.0008(6) 0.0055(7) -0.0067(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 N3 2.023(2) 5_766 ? Cu1 N3 2.023(2) . ? Cu1 N1 2.0272(19) 5_766 ? Cu1 N1 2.0272(19) . ? Cu1 O1 2.3243(16) . ? Cu1 O1 2.3243(16) 5_766 ? O1 C12 1.241(3) . ? O2 C15 1.214(3) . ? O3 C15 1.353(3) . ? O3 C16 1.472(2) . ? N1 C1 1.337(3) . ? N1 N2 1.373(2) . ? N2 C3 1.356(3) . ? N2 C11 1.450(3) . ? N3 C6 1.338(3) . ? N3 N4 1.376(2) . ? N4 C8 1.364(3) . ? N4 C11 1.454(3) . ? N5 C12 1.330(3) . ? N5 C13 1.465(3) . ? N6 C15 1.354(3) . ? N6 C14 1.454(3) . ? C1 C2 1.403(3) . ? C1 C4 1.495(3) . ? C2 C3 1.370(3) . ? C2 H2 0.9300 . ? C3 C5 1.495(3) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.400(3) . ? C6 C9 1.497(3) . ? C7 C8 1.371(3) . ? C7 H7 0.9300 . ? C8 C10 1.486(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.540(3) . ? C11 H11 0.9800 . ? C13 C14 1.526(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C16 C19 1.514(3) . ? C16 C18 1.516(3) . ? C16 C17 1.523(3) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? Cl1 O9 1.386(3) . ? Cl1 O7 1.416(3) . ? Cl1 O8 1.425(4) . ? Cl1 O10 1.436(4) . ? Cu2 N9 2.0102(16) 7_565 ? Cu2 N9 2.0102(16) . ? Cu2 N7 2.0124(16) . ? Cu2 N7 2.0124(16) 7_565 ? Cu2 O4 2.2944(14) 7_565 ? Cu2 O4 2.2944(14) . ? O4 C31 1.237(2) . ? O5 C34 1.226(3) . ? O6 C34 1.338(3) . ? O6 C35 1.477(3) . ? N7 C20 1.333(3) . ? N7 N8 1.373(2) . ? N8 C22 1.364(3) . ? N8 C30 1.449(2) . ? N9 C25 1.337(3) . ? N9 N10 1.370(2) 7_565 ? N10 C27 1.358(3) . ? N10 N9 1.370(2) 7_565 ? N10 C30 1.448(2) . ? N11 C31 1.322(3) . ? N11 C32 1.468(3) . ? N12 C34 1.353(3) . ? N12 C33 1.452(3) . ? C20 C21 1.402(3) . ? C20 C23 1.494(3) . ? C21 C22 1.373(3) . ? C21 H21 0.9300 . ? C22 C24 1.492(3) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.404(3) 7_565 ? C25 C28 1.493(3) . ? C26 C27 1.377(3) . ? C26 C25 1.404(3) 7_565 ? C26 H26 0.9300 . ? C27 C29 1.486(3) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 C31 1.547(3) . ? C30 H30 0.9800 . ? C32 C33 1.522(3) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C35 C36 1.507(4) . ? C35 C37 1.521(3) . ? C35 C38 1.526(3) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? Cl2 O14 1.341(9) . ? Cl2 O13 1.435(2) . ? Cl2 O16 1.437(7) . ? Cl2 O11 1.4441(16) . ? Cl2 O12 1.4513(17) . ? Cl2 O15 1.524(9) . ? O14 O15 0.623(12) . ? 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 N3 Cu1 N3 180.000(2) 5_766 . ? N3 Cu1 N1 86.64(8) 5_766 5_766 ? N3 Cu1 N1 93.36(8) . 5_766 ? N3 Cu1 N1 93.36(8) 5_766 . ? N3 Cu1 N1 86.64(8) . . ? N1 Cu1 N1 180.00(12) 5_766 . ? N3 Cu1 O1 95.88(7) 5_766 . ? N3 Cu1 O1 84.12(7) . . ? N1 Cu1 O1 94.70(7) 5_766 . ? N1 Cu1 O1 85.30(7) . . ? N3 Cu1 O1 84.12(7) 5_766 5_766 ? N3 Cu1 O1 95.88(7) . 5_766 ? N1 Cu1 O1 85.30(7) 5_766 5_766 ? N1 Cu1 O1 94.70(7) . 5_766 ? O1 Cu1 O1 180.0 . 5_766 ? C12 O1 Cu1 115.15(14) . . ? C15 O3 C16 120.64(16) . . ? C1 N1 N2 105.41(17) . . ? C1 N1 Cu1 135.97(15) . . ? N2 N1 Cu1 118.18(14) . . ? C3 N2 N1 111.50(18) . . ? C3 N2 C11 128.24(18) . . ? N1 N2 C11 119.75(17) . . ? C6 N3 N4 105.25(18) . . ? C6 N3 Cu1 136.08(15) . . ? N4 N3 Cu1 118.35(14) . . ? C8 N4 N3 111.50(17) . . ? C8 N4 C11 128.71(17) . . ? N3 N4 C11 119.46(17) . . ? C12 N5 C13 122.55(18) . . ? C15 N6 C14 121.03(18) . . ? N1 C1 C2 109.97(19) . . ? N1 C1 C4 122.7(2) . . ? C2 C1 C4 127.3(2) . . ? C3 C2 C1 106.8(2) . . ? C3 C2 H2 126.6 . . ? C1 C2 H2 126.6 . . ? N2 C3 C2 106.35(19) . . ? N2 C3 C5 122.4(2) . . ? C2 C3 C5 131.2(2) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N3 C6 C7 110.2(2) . . ? N3 C6 C9 122.1(2) . . ? C7 C6 C9 127.7(2) . . ? C8 C7 C6 107.0(2) . . ? C8 C7 H7 126.5 . . ? C6 C7 H7 126.5 . . ? N4 C8 C7 105.96(19) . . ? N4 C8 C10 123.56(19) . . ? C7 C8 C10 130.4(2) . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 N4 109.87(17) . . ? N2 C11 C12 111.02(17) . . ? N4 C11 C12 110.49(17) . . ? N2 C11 H11 108.5 . . ? N4 C11 H11 108.5 . . ? C12 C11 H11 108.5 . . ? O1 C12 N5 125.0(2) . . ? O1 C12 C11 119.94(18) . . ? N5 C12 C11 115.02(18) . . ? N5 C13 C14 112.31(17) . . ? N5 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? N5 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? N6 C14 C13 112.83(17) . . ? N6 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? N6 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? O2 C15 O3 126.10(19) . . ? O2 C15 N6 125.0(2) . . ? O3 C15 N6 108.85(17) . . ? O3 C16 C19 110.69(17) . . ? O3 C16 C18 110.72(17) . . ? C19 C16 C18 111.26(19) . . ? O3 C16 C17 102.15(17) . . ? C19 C16 C17 111.54(19) . . ? C18 C16 C17 110.14(18) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O9 Cl1 O7 112.1(2) . . ? O9 Cl1 O8 109.4(3) . . ? O7 Cl1 O8 105.8(3) . . ? O9 Cl1 O10 111.2(2) . . ? O7 Cl1 O10 110.9(2) . . ? O8 Cl1 O10 107.2(3) . . ? N9 Cu2 N9 180.00(12) 7_565 . ? N9 Cu2 N7 86.91(7) 7_565 . ? N9 Cu2 N7 93.09(7) . . ? N9 Cu2 N7 93.09(7) 7_565 7_565 ? N9 Cu2 N7 86.91(7) . 7_565 ? N7 Cu2 N7 180.00(12) . 7_565 ? N9 Cu2 O4 93.95(6) 7_565 7_565 ? N9 Cu2 O4 86.05(6) . 7_565 ? N7 Cu2 O4 94.35(6) . 7_565 ? N7 Cu2 O4 85.65(6) 7_565 7_565 ? N9 Cu2 O4 86.05(6) 7_565 . ? N9 Cu2 O4 93.95(6) . . ? N7 Cu2 O4 85.65(6) . . ? N7 Cu2 O4 94.35(6) 7_565 . ? O4 Cu2 O4 180.00(4) 7_565 . ? C31 O4 Cu2 114.07(12) . . ? C34 O6 C35 121.42(17) . . ? C20 N7 N8 105.69(16) . . ? C20 N7 Cu2 137.00(14) . . ? N8 N7 Cu2 117.09(12) . . ? C22 N8 N7 111.34(16) . . ? C22 N8 C30 128.66(16) . . ? N7 N8 C30 119.49(15) . . ? C25 N9 N10 105.58(16) . 7_565 ? C25 N9 Cu2 134.82(14) . . ? N10 N9 Cu2 117.43(12) 7_565 . ? C27 N10 N9 111.70(16) . 7_565 ? C27 N10 C30 128.50(17) . . ? N9 N10 C30 119.47(15) 7_565 . ? C31 N11 C32 123.05(17) . . ? C34 N12 C33 122.73(19) . . ? N7 C20 C21 110.08(18) . . ? N7 C20 C23 122.15(18) . . ? C21 C20 C23 127.76(19) . . ? C22 C21 C20 106.90(18) . . ? C22 C21 H21 126.5 . . ? C20 C21 H21 126.5 . . ? N8 C22 C21 105.97(17) . . ? N8 C22 C24 122.69(18) . . ? C21 C22 C24 131.34(19) . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N9 C25 C26 109.97(18) . 7_565 ? N9 C25 C28 121.85(18) . . ? C26 C25 C28 128.18(19) 7_565 . ? C27 C26 C25 106.71(18) . 7_565 ? C27 C26 H26 126.6 . . ? C25 C26 H26 126.6 7_565 . ? N10 C27 C26 106.03(18) . . ? N10 C27 C29 122.41(19) . . ? C26 C27 C29 131.56(19) . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N10 C30 N8 109.72(15) . . ? N10 C30 C31 110.54(15) . . ? N8 C30 C31 110.24(15) . . ? N10 C30 H30 108.8 . . ? N8 C30 H30 108.8 . . ? C31 C30 H30 108.8 . . ? O4 C31 N11 125.46(18) . . ? O4 C31 C30 120.06(17) . . ? N11 C31 C30 114.48(16) . . ? N11 C32 C33 110.34(17) . . ? N11 C32 H32A 109.6 . . ? C33 C32 H32A 109.6 . . ? N11 C32 H32B 109.6 . . ? C33 C32 H32B 109.6 . . ? H32A C32 H32B 108.1 . . ? N12 C33 C32 112.89(18) . . ? N12 C33 H33A 109.0 . . ? C32 C33 H33A 109.0 . . ? N12 C33 H33B 109.0 . . ? C32 C33 H33B 109.0 . . ? H33A C33 H33B 107.8 . . ? O5 C34 O6 125.4(2) . . ? O5 C34 N12 124.6(2) . . ? O6 C34 N12 110.01(19) . . ? O6 C35 C36 109.9(2) . . ? O6 C35 C37 110.63(19) . . ? C36 C35 C37 112.8(2) . . ? O6 C35 C38 102.12(19) . . ? C36 C35 C38 110.5(2) . . ? C37 C35 C38 110.4(2) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C35 C38 H38A 109.5 . . ? C35 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C35 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? O14 Cl2 O13 98.8(4) . . ? O14 Cl2 O16 12.2(6) . . ? O13 Cl2 O16 110.3(4) . . ? O14 Cl2 O11 112.2(4) . . ? O13 Cl2 O11 109.56(12) . . ? O16 Cl2 O11 110.5(3) . . ? O14 Cl2 O12 118.3(4) . . ? O13 Cl2 O12 108.21(11) . . ? O16 Cl2 O12 109.2(3) . . ? O11 Cl2 O12 109.07(10) . . ? O14 Cl2 O15 24.1(5) . . ? O13 Cl2 O15 121.8(3) . . ? O16 Cl2 O15 11.9(5) . . ? O11 Cl2 O15 106.2(3) . . ? O12 Cl2 O15 101.2(3) . . ? O15 O14 Cl2 94.7(10) . . ? O14 O15 Cl2 61.3(9) . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 -0.006 919.4 -3.9 2 0.354 0.190 0.969 10.9 -0.4 3 0.646 0.190 0.531 10.9 -0.3 4 0.500 0.500 0.573 919.4 -3.9 5 0.146 0.310 0.031 10.9 -0.4 6 0.854 0.310 0.469 10.9 -0.4 7 0.146 0.690 0.531 10.9 -0.3 8 0.854 0.690 0.969 10.9 -0.4 9 0.354 0.810 0.469 10.9 -0.4 10 0.646 0.810 0.031 10.9 -0.4 _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.118 _refine_diff_density_min -0.621 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 916433' ####################################################################### # # 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_mo_am_077_sb_015b_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H60 Cu N12 O6,C4 H6 N2,O2,2(C2 H3 N),2(Cl)' _chemical_formula_sum 'C46 H72 Cl2 Cu N16 O8' _chemical_formula_weight 1111.65 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9692(10) _cell_length_b 10.5011(11) _cell_length_c 14.4625(16) _cell_angle_alpha 69.076(2) _cell_angle_beta 70.144(2) _cell_angle_gamma 82.168(2) _cell_volume 1329.9(2) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9978 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 28.33 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 591 _exptl_absorpt_coefficient_mu 0.578 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6726 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details (SADABS,Sheldrick,bruker,2001) _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23922 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 28.28 _reflns_number_total 6563 _reflns_number_gt 6111 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0810P)^2^+2.1095P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6563 _refine_ls_number_parameters 340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1447 _refine_ls_wR_factor_gt 0.1419 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 0.0000 0.5000 0.5000 0.01016(11) Uani 1 2 d S . . Cl1 Cl 0.21893(6) 0.71192(5) 0.98188(4) 0.02077(13) Uani 1 1 d . . . O1 O -0.01196(16) 0.30313(15) 0.63793(11) 0.0140(3) Uani 1 1 d . . . O2 O 0.2177(2) 0.25141(18) 0.77910(13) 0.0267(4) Uani 1 1 d . . . O3 O 0.26680(18) 0.12608(16) 0.93014(12) 0.0195(3) Uani 1 1 d . . . N4 N 0.02130(18) 0.54651(17) 0.68312(13) 0.0120(3) Uani 1 1 d . . . N3 N 0.08047(18) 0.58321(17) 0.57664(13) 0.0125(3) Uani 1 1 d . . . N2 N -0.21645(18) 0.52110(17) 0.69248(13) 0.0118(3) Uani 1 1 d . . . N1 N -0.19760(18) 0.54105(18) 0.58964(13) 0.0126(3) Uani 1 1 d . . . N5 N -0.1062(2) 0.21319(18) 0.81433(14) 0.0153(3) Uani 1 1 d . . . H5 H -0.1463 0.2302 0.8716 0.018 Uiso 1 1 calc R . . N6 N 0.1322(2) 0.03694(19) 0.87451(15) 0.0197(4) Uani 1 1 d . . . H6 H 0.1192 -0.0282 0.9332 0.024 Uiso 1 1 calc R . . C12 C -0.0670(2) 0.3161(2) 0.72528(15) 0.0125(4) Uani 1 1 d . . . C11 C -0.1022(2) 0.45911(19) 0.73586(15) 0.0114(3) Uani 1 1 d . . . H2 H -0.1347 0.4493 0.8100 0.014 Uiso 1 1 calc R . . C8 C 0.0812(2) 0.6135(2) 0.72399(16) 0.0141(4) Uani 1 1 d . . . C7 C 0.1862(2) 0.6933(2) 0.64077(17) 0.0160(4) Uani 1 1 d . . . H7 H 0.2480 0.7497 0.6437 0.019 Uiso 1 1 calc R . . C6 C 0.1817(2) 0.6731(2) 0.55114(16) 0.0144(4) Uani 1 1 d . . . C9 C 0.2713(2) 0.7397(2) 0.44088(17) 0.0196(4) Uani 1 1 d . . . H9A H 0.3342 0.6730 0.4160 0.029 Uiso 1 1 calc R . . H9B H 0.3264 0.8102 0.4378 0.029 Uiso 1 1 calc R . . H9C H 0.2107 0.7788 0.3981 0.029 Uiso 1 1 calc R . . C10 C 0.0267(3) 0.6034(2) 0.83606(17) 0.0196(4) Uani 1 1 d . . . H10A H -0.0571 0.6602 0.8476 0.029 Uiso 1 1 calc R . . H10B H 0.0987 0.6329 0.8538 0.029 Uiso 1 1 calc R . . H10C H 0.0033 0.5105 0.8788 0.029 Uiso 1 1 calc R . . C3 C -0.3449(2) 0.5702(2) 0.73927(16) 0.0143(4) Uani 1 1 d . . . C2 C -0.4131(2) 0.6201(2) 0.66445(17) 0.0168(4) Uani 1 1 d . . . H2A H -0.5043 0.6588 0.6732 0.020 Uiso 1 1 calc R . . C1 C -0.3187(2) 0.6015(2) 0.57272(16) 0.0141(4) Uani 1 1 d . . . C4 C -0.3413(2) 0.6413(2) 0.46894(17) 0.0192(4) Uani 1 1 d . . . H4A H -0.2530 0.6717 0.4146 0.029 Uiso 1 1 calc R . . H4B H -0.4113 0.7137 0.4632 0.029 Uiso 1 1 calc R . . H4C H -0.3741 0.5641 0.4624 0.029 Uiso 1 1 calc R . . C5 C -0.3883(2) 0.5700(2) 0.84877(17) 0.0203(4) Uani 1 1 d . . . H5A H -0.3781 0.4794 0.8944 0.030 Uiso 1 1 calc R . . H5B H -0.4860 0.5999 0.8691 0.030 Uiso 1 1 calc R . . H5C H -0.3287 0.6307 0.8533 0.030 Uiso 1 1 calc R . . C13 C -0.0825(3) 0.0711(2) 0.81730(17) 0.0186(4) Uani 1 1 d . . . H13A H -0.1157 0.0598 0.7650 0.022 Uiso 1 1 calc R . . H13B H -0.1381 0.0122 0.8850 0.022 Uiso 1 1 calc R . . C14 C 0.0740(3) 0.0277(2) 0.79749(18) 0.0201(4) Uani 1 1 d . . . H14A H 0.0842 -0.0656 0.7978 0.024 Uiso 1 1 calc R . . H14B H 0.1290 0.0849 0.7288 0.024 Uiso 1 1 calc R . . C15 C 0.2070(3) 0.1479(2) 0.85404(17) 0.0191(4) Uani 1 1 d . . . C16 C 0.3599(2) 0.2297(2) 0.92205(18) 0.0189(4) Uani 1 1 d . . . C17 C 0.3936(3) 0.1709(3) 1.02473(19) 0.0245(5) Uani 1 1 d . . . H17A H 0.3077 0.1677 1.0817 0.037 Uiso 1 1 calc R . . H17B H 0.4614 0.2275 1.0248 0.037 Uiso 1 1 calc R . . H17C H 0.4329 0.0804 1.0324 0.037 Uiso 1 1 calc R . . C18 C 0.2811(3) 0.3663(2) 0.9146(2) 0.0247(5) Uani 1 1 d . . . H18A H 0.2770 0.4107 0.8449 0.037 Uiso 1 1 calc R . . H18B H 0.3306 0.4227 0.9315 0.037 Uiso 1 1 calc R . . H18C H 0.1859 0.3514 0.9626 0.037 Uiso 1 1 calc R . . C19 C 0.4947(3) 0.2400(3) 0.8293(2) 0.0275(5) Uani 1 1 d . . . H19A H 0.5397 0.1516 0.8368 0.041 Uiso 1 1 calc R . . H19B H 0.5592 0.3020 0.8269 0.041 Uiso 1 1 calc R . . H19C H 0.4701 0.2727 0.7660 0.041 Uiso 1 1 calc R . . C23 C 0.5397(5) 0.0509(5) 0.3278(7) 0.086(2) Uani 1 1 d . . . C21 C 0.1572(3) 0.1177(3) 0.4051(3) 0.0316(6) Uani 1 1 d . . . C20 C 0.1569(3) 0.0845(3) 0.5116(2) 0.0346(6) Uani 1 1 d . . . H20A H 0.1126 -0.0020 0.5535 0.052 Uiso 1 1 calc R . . H20B H 0.1046 0.1537 0.5392 0.052 Uiso 1 1 calc R . . H20C H 0.2532 0.0799 0.5126 0.052 Uiso 1 1 calc R . . C22 C 0.5526(7) 0.0384(7) 0.4200(5) 0.0862(17) Uani 1 1 d . . . H22A H 0.4643 0.0074 0.4741 0.129 Uiso 1 1 calc R . . H22B H 0.5752 0.1252 0.4185 0.129 Uiso 1 1 calc R . . H22C H 0.6273 -0.0265 0.4333 0.129 Uiso 1 1 calc R . . N7 N 0.1568(3) 0.1425(3) 0.3210(2) 0.0419(6) Uani 1 1 d . . . N8 N 0.5247(7) 0.0658(6) 0.2491(5) 0.107(2) Uani 1 1 d . . . O4 O 0.6511(4) 0.1584(4) 0.2601(3) 0.0735(9) 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 0.01010(17) 0.01210(17) 0.00818(17) -0.00318(12) -0.00281(12) -0.00055(11) Cl1 0.0320(3) 0.0165(2) 0.0136(2) -0.00431(18) -0.0079(2) 0.00028(19) O1 0.0181(7) 0.0130(7) 0.0103(6) -0.0033(5) -0.0046(5) 0.0006(5) O2 0.0427(11) 0.0186(8) 0.0166(8) 0.0020(6) -0.0119(7) -0.0086(7) O3 0.0267(8) 0.0179(7) 0.0137(7) -0.0016(6) -0.0082(6) -0.0060(6) N4 0.0128(8) 0.0127(7) 0.0106(7) -0.0037(6) -0.0037(6) -0.0005(6) N3 0.0132(8) 0.0139(8) 0.0091(7) -0.0025(6) -0.0028(6) -0.0016(6) N2 0.0122(8) 0.0136(8) 0.0091(7) -0.0036(6) -0.0033(6) 0.0000(6) N1 0.0132(8) 0.0148(8) 0.0091(7) -0.0031(6) -0.0038(6) 0.0000(6) N5 0.0202(9) 0.0136(8) 0.0106(8) -0.0027(6) -0.0035(6) -0.0027(6) N6 0.0305(10) 0.0138(8) 0.0158(9) -0.0010(7) -0.0122(8) -0.0017(7) C12 0.0130(9) 0.0124(8) 0.0125(9) -0.0034(7) -0.0054(7) -0.0006(7) C11 0.0128(9) 0.0119(8) 0.0088(8) -0.0026(7) -0.0033(7) -0.0007(7) C8 0.0151(9) 0.0140(9) 0.0163(9) -0.0070(7) -0.0078(7) 0.0023(7) C7 0.0160(9) 0.0155(9) 0.0189(10) -0.0061(8) -0.0080(8) -0.0007(7) C6 0.0126(9) 0.0145(9) 0.0155(9) -0.0039(7) -0.0045(7) -0.0005(7) C9 0.0176(10) 0.0222(10) 0.0166(10) -0.0034(8) -0.0029(8) -0.0078(8) C10 0.0244(11) 0.0226(10) 0.0159(10) -0.0095(8) -0.0079(8) -0.0004(8) C3 0.0130(9) 0.0137(9) 0.0146(9) -0.0053(7) -0.0016(7) -0.0003(7) C2 0.0136(9) 0.0170(9) 0.0186(10) -0.0057(8) -0.0051(8) 0.0028(7) C1 0.0128(9) 0.0134(9) 0.0149(9) -0.0023(7) -0.0054(7) -0.0004(7) C4 0.0180(10) 0.0234(10) 0.0165(10) -0.0042(8) -0.0094(8) 0.0025(8) C5 0.0190(10) 0.0264(11) 0.0155(10) -0.0111(8) -0.0023(8) 0.0032(8) C13 0.0282(11) 0.0126(9) 0.0151(9) -0.0015(7) -0.0084(8) -0.0053(8) C14 0.0315(12) 0.0145(9) 0.0179(10) -0.0058(8) -0.0124(9) 0.0013(8) C15 0.0263(11) 0.0170(10) 0.0132(9) -0.0042(8) -0.0060(8) -0.0012(8) C16 0.0207(10) 0.0163(10) 0.0196(10) -0.0068(8) -0.0042(8) -0.0028(8) C17 0.0288(12) 0.0243(11) 0.0250(11) -0.0097(9) -0.0125(10) -0.0011(9) C18 0.0280(12) 0.0194(11) 0.0266(12) -0.0103(9) -0.0071(9) 0.0026(9) C19 0.0239(12) 0.0237(11) 0.0264(12) -0.0071(9) 0.0015(9) -0.0020(9) C23 0.043(2) 0.035(2) 0.182(7) -0.028(3) -0.047(4) 0.0042(16) C21 0.0195(11) 0.0187(11) 0.0491(17) -0.0117(11) -0.0010(11) -0.0013(9) C20 0.0286(13) 0.0247(12) 0.0463(16) -0.0164(12) -0.0010(11) -0.0029(10) C22 0.086(4) 0.100(4) 0.080(4) -0.022(3) -0.047(3) 0.005(3) N7 0.0312(13) 0.0351(13) 0.0493(17) -0.0087(12) -0.0058(11) -0.0006(10) N8 0.085(4) 0.082(4) 0.116(5) -0.036(4) 0.026(3) -0.019(3) O4 0.071(2) 0.075(2) 0.078(2) -0.0331(18) -0.0188(17) -0.0066(17) _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 N3 2.0305(17) . ? Cu1 N3 2.0305(17) 2_566 ? Cu1 N1 2.0445(17) . ? Cu1 N1 2.0445(17) 2_566 ? Cu1 O1 2.2863(14) . ? Cu1 O1 2.2863(14) 2_566 ? O1 C12 1.244(2) . ? O2 C15 1.216(3) . ? O3 C15 1.359(3) . ? O3 C16 1.473(3) . ? N4 C8 1.361(3) . ? N4 N3 1.374(2) . ? N4 C11 1.452(2) . ? N3 C6 1.343(3) . ? N2 C3 1.358(3) . ? N2 N1 1.375(2) . ? N2 C11 1.451(2) . ? N1 C1 1.342(3) . ? N5 C12 1.326(3) . ? N5 C13 1.466(3) . ? N5 H5 0.8600 . ? N6 C15 1.357(3) . ? N6 C14 1.455(3) . ? N6 H6 0.8600 . ? C12 C11 1.545(3) . ? C11 H2 0.9800 . ? C8 C7 1.382(3) . ? C8 C10 1.493(3) . ? C7 C6 1.402(3) . ? C7 H7 0.9300 . ? C6 C9 1.495(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C3 C2 1.380(3) . ? C3 C5 1.493(3) . ? C2 C1 1.404(3) . ? C2 H2A 0.9300 . ? C1 C4 1.495(3) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C13 C14 1.524(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C16 C18 1.525(3) . ? C16 C17 1.526(3) . ? C16 C19 1.526(3) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C23 N8 1.151(9) . ? C23 C22 1.340(10) . ? C21 N7 1.149(4) . ? C21 C20 1.453(5) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N3 180.000(1) . 2_566 ? N3 Cu1 N1 86.79(7) . . ? N3 Cu1 N1 93.21(7) 2_566 . ? N3 Cu1 N1 93.21(7) . 2_566 ? N3 Cu1 N1 86.79(7) 2_566 2_566 ? N1 Cu1 N1 180.0 . 2_566 ? N3 Cu1 O1 85.41(6) . . ? N3 Cu1 O1 94.59(6) 2_566 . ? N1 Cu1 O1 84.59(6) . . ? N1 Cu1 O1 95.41(6) 2_566 . ? N3 Cu1 O1 94.59(6) . 2_566 ? N3 Cu1 O1 85.41(6) 2_566 2_566 ? N1 Cu1 O1 95.41(6) . 2_566 ? N1 Cu1 O1 84.59(6) 2_566 2_566 ? O1 Cu1 O1 180.00(7) . 2_566 ? C12 O1 Cu1 114.92(13) . . ? C15 O3 C16 119.81(17) . . ? C8 N4 N3 111.93(16) . . ? C8 N4 C11 128.01(17) . . ? N3 N4 C11 119.61(16) . . ? C6 N3 N4 105.21(16) . . ? C6 N3 Cu1 136.78(14) . . ? N4 N3 Cu1 118.00(12) . . ? C3 N2 N1 111.87(16) . . ? C3 N2 C11 128.58(17) . . ? N1 N2 C11 119.49(16) . . ? C1 N1 N2 105.42(16) . . ? C1 N1 Cu1 136.23(14) . . ? N2 N1 Cu1 117.72(12) . . ? C12 N5 C13 121.46(18) . . ? C12 N5 H5 119.3 . . ? C13 N5 H5 119.3 . . ? C15 N6 C14 120.23(18) . . ? C15 N6 H6 119.9 . . ? C14 N6 H6 119.9 . . ? O1 C12 N5 124.57(19) . . ? O1 C12 C11 120.56(17) . . ? N5 C12 C11 114.79(17) . . ? N2 C11 N4 109.68(15) . . ? N2 C11 C12 109.05(16) . . ? N4 C11 C12 111.81(16) . . ? N2 C11 H2 108.7 . . ? N4 C11 H2 108.7 . . ? C12 C11 H2 108.7 . . ? N4 C8 C7 105.83(18) . . ? N4 C8 C10 122.87(19) . . ? C7 C8 C10 131.10(19) . . ? C8 C7 C6 106.79(18) . . ? C8 C7 H7 126.6 . . ? C6 C7 H7 126.6 . . ? N3 C6 C7 110.21(18) . . ? N3 C6 C9 122.28(19) . . ? C7 C6 C9 127.50(19) . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C3 C2 105.82(18) . . ? N2 C3 C5 122.79(19) . . ? C2 C3 C5 131.34(19) . . ? C3 C2 C1 107.01(18) . . ? C3 C2 H2A 126.5 . . ? C1 C2 H2A 126.5 . . ? N1 C1 C2 109.85(18) . . ? N1 C1 C4 122.36(19) . . ? C2 C1 C4 127.79(19) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N5 C13 C14 112.36(18) . . ? N5 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? N5 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.9 . . ? N6 C14 C13 113.08(19) . . ? N6 C14 H14A 109.0 . . ? C13 C14 H14A 109.0 . . ? N6 C14 H14B 109.0 . . ? C13 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? O2 C15 N6 124.9(2) . . ? O2 C15 O3 125.4(2) . . ? N6 C15 O3 109.77(18) . . ? O3 C16 C18 111.00(19) . . ? O3 C16 C17 102.74(17) . . ? C18 C16 C17 110.18(19) . . ? O3 C16 C19 109.03(19) . . ? C18 C16 C19 112.4(2) . . ? C17 C16 C19 111.0(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N8 C23 C22 177.2(7) . . ? N7 C21 C20 179.2(3) . . ? C21 C20 H20A 109.5 . . ? C21 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C21 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C23 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C23 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.584 _refine_diff_density_min -1.328 _refine_diff_density_rms 0.108 _database_code_depnum_ccdc_archive 'CCDC 916434' ####################################################################### # # 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_mo_am_094_as_013_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H52 Cu N10 O6 S2, 2(Cl O4), (CH2Cl2)' _chemical_formula_sum 'C37 H54 Cl4 Cu N10 O14 S2' _chemical_formula_weight 1132.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P1 _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 10.9216(11) _cell_length_b 11.5633(11) _cell_length_c 13.5707(13) _cell_angle_alpha 71.247(2) _cell_angle_beta 69.310(2) _cell_angle_gamma 85.255(2) _cell_volume 1517.3(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9927 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 28.38 _exptl_crystal_description red _exptl_crystal_colour rhombic _exptl_crystal_size_max 0.248 _exptl_crystal_size_mid 0.126 _exptl_crystal_size_min 0.097 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 673 _exptl_absorpt_coefficient_mu 0.684 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6421 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details (SADABS,Sheldrick,bruker,2001) _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18417 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.00 _reflns_number_total 9750 _reflns_number_gt 8776 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement "'SHELXS-97 (Sheldrick, 2008)" _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0880P)^2^+1.1806P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.125(13) _refine_ls_number_reflns 9750 _refine_ls_number_parameters 625 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1463 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.18090(5) 0.08607(4) 0.15057(4) 0.01825(12) Uani 1 1 d . . . Cl2 Cl 0.81481(14) 0.90462(11) 0.85565(9) 0.0330(3) Uani 1 1 d . . . O6 O 0.1650(6) -0.4490(4) 0.0272(4) 0.0610(14) Uani 1 1 d . . . Cl1 Cl 0.55297(15) 0.23847(14) 0.46119(11) 0.0415(4) Uani 1 1 d . . . Cl4 Cl 1.0214(2) 0.26031(15) 0.50690(13) 0.0573(4) Uani 1 1 d . . . Cl3 Cl 0.7973(4) 0.3069(3) 0.67639(17) 0.1149(12) Uani 1 1 d . . . S1 S 0.1357(2) 0.56681(16) 0.38190(18) 0.0743(7) Uani 1 1 d . . . S2 S -0.3038(2) -0.3563(2) 0.3317(2) 0.0792(7) Uani 1 1 d . . . O13 O 0.8376(6) 0.8368(5) 0.7812(4) 0.0681(18) Uani 1 1 d . . . O14 O 0.7160(6) 0.9926(5) 0.8403(5) 0.0707(16) Uani 1 1 d . . . O12 O 0.9333(5) 0.9699(3) 0.8333(3) 0.0371(10) Uani 1 1 d . . . O11 O 0.7771(5) 0.8205(4) 0.9661(3) 0.0466(11) Uani 1 1 d . . . O1 O 0.2639(4) 0.2505(3) 0.1755(3) 0.0289(9) Uani 1 1 d . . . C4 C 0.4163(6) -0.1167(5) 0.0361(4) 0.0308(13) Uani 1 1 d . . . H4A H 0.4448 -0.0537 -0.0344 0.046 Uiso 1 1 calc R . . H4B H 0.3256 -0.1378 0.0559 0.046 Uiso 1 1 calc R . . H4C H 0.4677 -0.1875 0.0315 0.046 Uiso 1 1 calc R . . O3 O 0.5566(4) 0.3814(3) 0.0812(3) 0.0348(9) Uani 1 1 d . . . N8 N 0.0187(5) 0.1675(3) 0.1279(3) 0.0185(9) Uani 1 1 d . . . C20 C 0.3584(7) 0.2260(5) -0.2016(4) 0.0345(14) Uani 1 1 d . . . H20 H 0.4211 0.2671 -0.2691 0.041 Uiso 1 1 calc R . . C22 C 0.4824(6) 0.2248(5) -0.0677(4) 0.0300(12) Uani 1 1 d . . . H22A H 0.5210 0.1499 -0.0386 0.045 Uiso 1 1 calc R . . H22B H 0.4523 0.2669 -0.0133 0.045 Uiso 1 1 calc R . . H22C H 0.5465 0.2755 -0.1336 0.045 Uiso 1 1 calc R . . N10 N 0.0369(6) -0.1466(4) 0.0156(4) 0.0372(13) Uani 1 1 d . . . O7 O 0.4360(6) 0.1708(6) 0.4805(5) 0.0691(17) Uani 1 1 d . . . O10 O 0.6101(6) 0.3033(6) 0.3460(3) 0.0741(18) Uani 1 1 d . . . O8 O 0.5138(8) 0.3173(6) 0.5255(5) 0.096(3) Uani 1 1 d . . . O9 O 0.6452(10) 0.1609(9) 0.4969(8) 0.133(4) Uani 1 1 d . . . C11 C 0.3118(5) 0.0895(4) 0.3184(4) 0.0194(10) Uani 1 1 d . . . H11 H 0.3526 0.0876 0.3726 0.023 Uiso 1 1 calc R . . C1 C 0.4329(5) -0.0713(4) 0.1227(4) 0.0217(10) Uani 1 1 d . . . C8 C 0.1240(6) -0.0229(4) 0.4894(4) 0.0252(11) Uani 1 1 d . . . O4 O 0.4761(5) 0.5710(3) 0.0364(3) 0.0465(11) Uani 1 1 d . . . N6 N 0.2588(5) 0.1388(3) -0.0187(3) 0.0221(9) Uani 1 1 d . . . C19 C 0.3689(6) 0.1969(4) -0.0952(4) 0.0236(11) Uani 1 1 d . . . C12 C 0.3059(5) 0.2261(4) 0.2483(3) 0.0177(10) Uani 1 1 d . . . N2 N 0.3933(4) 0.0238(3) 0.2441(3) 0.0188(8) Uani 1 1 d . . . N1 N 0.3451(5) 0.0040(4) 0.1685(3) 0.0224(9) Uani 1 1 d . . . C2 C 0.5324(6) -0.0968(5) 0.1678(4) 0.0316(13) Uani 1 1 d . . . H2 H 0.6040 -0.1449 0.1490 0.038 Uiso 1 1 calc R . . C3 C 0.5038(6) -0.0361(4) 0.2469(4) 0.0246(11) Uani 1 1 d . . . C5 C 0.5798(7) -0.0260(6) 0.3186(6) 0.0431(16) Uani 1 1 d . . . H5A H 0.5205 -0.0365 0.3928 0.065 Uiso 1 1 calc R . . H5B H 0.6231 0.0530 0.2886 0.065 Uiso 1 1 calc R . . H5C H 0.6437 -0.0882 0.3196 0.065 Uiso 1 1 calc R . . N4 N 0.1817(4) 0.0362(3) 0.3772(3) 0.0222(9) Uani 1 1 d . . . N3 N 0.1022(4) 0.0321(3) 0.3190(3) 0.0199(9) Uani 1 1 d . . . C6 C -0.0086(6) -0.0243(4) 0.3953(4) 0.0239(11) Uani 1 1 d . . . C9 C -0.1237(6) -0.0453(5) 0.3663(4) 0.0315(13) Uani 1 1 d . . . H9B H -0.0935 -0.0506 0.2924 0.047 Uiso 1 1 calc R . . H9A H -0.1817 0.0214 0.3704 0.047 Uiso 1 1 calc R . . H9C H -0.1695 -0.1202 0.4176 0.047 Uiso 1 1 calc R . . C7 C -0.0009(6) -0.0601(5) 0.5021(4) 0.0284(12) Uani 1 1 d . . . H7 H -0.0660 -0.1005 0.5682 0.034 Uiso 1 1 calc R . . C10 C 0.1889(7) -0.0361(7) 0.5722(4) 0.0453(17) Uani 1 1 d . . . H10C H 0.2712 -0.0744 0.5507 0.068 Uiso 1 1 calc R . . H10B H 0.1336 -0.0854 0.6439 0.068 Uiso 1 1 calc R . . H10A H 0.2036 0.0432 0.5754 0.068 Uiso 1 1 calc R . . N5 N 0.3545(5) 0.3073(4) 0.2795(4) 0.0297(10) Uani 1 1 d . . . C13 C 0.3675(6) 0.4367(4) 0.2153(4) 0.0301(12) Uani 1 1 d . . . H13 H 0.2862 0.4629 0.2007 0.036 Uiso 1 1 calc R . . C14 C 0.4806(6) 0.4548(4) 0.1054(4) 0.0287(11) Uani 1 1 d . . . C15 C 0.5808(9) 0.6013(6) -0.0669(6) 0.072(3) Uani 1 1 d . . . H15A H 0.5971 0.5325 -0.0943 0.108 Uiso 1 1 calc R . . H15B H 0.6581 0.6221 -0.0572 0.108 Uiso 1 1 calc R . . H15C H 0.5580 0.6697 -0.1191 0.108 Uiso 1 1 calc R . . C16 C 0.3941(6) 0.5117(5) 0.2832(5) 0.0393(13) Uani 1 1 d . . . H16A H 0.4737 0.4841 0.2987 0.047 Uiso 1 1 calc R . . H16B H 0.4082 0.5972 0.2387 0.047 Uiso 1 1 calc R . . C17 C 0.2801(8) 0.4994(6) 0.3943(5) 0.0501(18) Uani 1 1 d . . . H17A H 0.3092 0.5355 0.4380 0.060 Uiso 1 1 calc R . . H17B H 0.2612 0.4133 0.4351 0.060 Uiso 1 1 calc R . . C18 C 0.1722(11) 0.7255(6) 0.3413(7) 0.072(3) Uani 1 1 d . . . H18A H 0.2488 0.7475 0.2756 0.108 Uiso 1 1 calc R . . H18B H 0.1880 0.7441 0.3999 0.108 Uiso 1 1 calc R . . H18C H 0.0996 0.7708 0.3264 0.108 Uiso 1 1 calc R . . N9 N -0.0276(4) 0.1400(3) 0.0569(3) 0.0200(9) Uani 1 1 d . . . C29 C 0.0511(5) 0.0714(4) -0.0159(4) 0.0188(10) Uani 1 1 d . . . H29 H 0.0098 0.0730 -0.0698 0.023 Uiso 1 1 calc R . . N7 N 0.1808(5) 0.1306(3) -0.0752(3) 0.0202(9) Uani 1 1 d . . . C21 C 0.2410(6) 0.1830(5) -0.1860(4) 0.0282(12) Uani 1 1 d . . . C23 C 0.1758(7) 0.1914(6) -0.2677(5) 0.0434(16) Uani 1 1 d . . . H23A H 0.2407 0.2074 -0.3405 0.065 Uiso 1 1 calc R . . H23B H 0.1153 0.2566 -0.2673 0.065 Uiso 1 1 calc R . . H23C H 0.1294 0.1157 -0.2479 0.065 Uiso 1 1 calc R . . C30 C 0.0598(6) -0.0613(4) 0.0517(4) 0.0258(11) Uani 1 1 d . . . C31 C 0.0507(9) -0.2780(5) 0.0722(5) 0.055(2) Uani 1 1 d . . . H31 H 0.1071 -0.2832 0.1157 0.066 Uiso 1 1 calc R . . C34 C -0.0769(10) -0.3445(6) 0.1490(6) 0.068(2) Uani 1 1 d . . . H34A H -0.0601 -0.4255 0.1913 0.081 Uiso 1 1 calc R . . H34B H -0.1281 -0.3534 0.1060 0.081 Uiso 1 1 calc R . . C35 C -0.1552(9) -0.2731(8) 0.2293(6) 0.071(3) Uani 1 1 d . . . H35A H -0.1779 -0.1948 0.1870 0.085 Uiso 1 1 calc R . . H35B H -0.1006 -0.2578 0.2670 0.085 Uiso 1 1 calc R . . C33 C 0.2061(15) -0.5243(7) -0.0465(7) 0.105(5) Uani 1 1 d . . . H33A H 0.2804 -0.5700 -0.0359 0.158 Uiso 1 1 calc R . . H33B H 0.2294 -0.4726 -0.1222 0.158 Uiso 1 1 calc R . . H33C H 0.1354 -0.5796 -0.0299 0.158 Uiso 1 1 calc R . . O2 O 0.0970(4) -0.0843(3) 0.1348(2) 0.0218(8) Uani 1 1 d . . . C26 C -0.1414(6) 0.1946(5) 0.0559(4) 0.0294(12) Uani 1 1 d . . . C25 C -0.1716(6) 0.2581(4) 0.1304(4) 0.0269(11) Uani 1 1 d . . . H25 H -0.2454 0.3039 0.1490 0.032 Uiso 1 1 calc R . . C24 C -0.0705(6) 0.2407(4) 0.1727(4) 0.0253(11) Uani 1 1 d . . . C27 C -0.0530(6) 0.2919(5) 0.2564(4) 0.0298(13) Uani 1 1 d . . . H27A H 0.0046 0.3630 0.2183 0.045 Uiso 1 1 calc R . . H27B H -0.0161 0.2314 0.3043 0.045 Uiso 1 1 calc R . . H27C H -0.1365 0.3139 0.2997 0.045 Uiso 1 1 calc R . . C28 C -0.2124(7) 0.1817(5) -0.0162(5) 0.0340(13) Uani 1 1 d . . . H28A H -0.2918 0.2258 -0.0027 0.051 Uiso 1 1 calc R . . H28B H -0.2329 0.0969 0.0005 0.051 Uiso 1 1 calc R . . H28C H -0.1580 0.2142 -0.0927 0.051 Uiso 1 1 calc R . . C37 C 0.8658(9) 0.2050(8) 0.6003(5) 0.066(2) Uani 1 1 d . . . H37A H 0.8718 0.1249 0.6504 0.080 Uiso 1 1 calc R . . H37B H 0.8103 0.1972 0.5604 0.080 Uiso 1 1 calc R . . C36 C -0.2437(16) -0.4650(8) 0.4196(9) 0.117(5) Uani 1 1 d . . . H36A H -0.1869 -0.4269 0.4412 0.176 Uiso 1 1 calc R . . H36B H -0.1954 -0.5217 0.3830 0.176 Uiso 1 1 calc R . . H36C H -0.3149 -0.5077 0.4842 0.176 Uiso 1 1 calc R . . O5 O 0.1261(7) -0.3012(4) -0.1114(4) 0.0632(15) Uani 1 1 d . . . C32 C 0.1199(9) -0.3374(5) -0.0179(6) 0.058(2) 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 0.0151(3) 0.0235(2) 0.01812(19) -0.00804(15) -0.00750(17) 0.00396(17) Cl2 0.0311(8) 0.0416(6) 0.0253(5) -0.0089(4) -0.0086(5) -0.0058(5) O6 0.085(4) 0.042(2) 0.061(3) -0.0182(19) -0.034(3) 0.024(2) Cl1 0.0294(9) 0.0704(9) 0.0313(6) -0.0224(6) -0.0117(6) -0.0027(7) Cl4 0.0606(12) 0.0615(8) 0.0581(8) -0.0203(7) -0.0266(8) -0.0074(8) Cl3 0.138(3) 0.1188(19) 0.0446(9) -0.0137(11) 0.0007(13) 0.0404(19) S1 0.0630(14) 0.0465(8) 0.0884(12) -0.0353(8) 0.0162(11) -0.0006(9) S2 0.0539(14) 0.0700(11) 0.0882(14) -0.0025(10) -0.0126(11) -0.0081(10) O13 0.089(5) 0.087(3) 0.040(2) -0.042(2) -0.009(3) -0.030(3) O14 0.030(3) 0.062(3) 0.105(4) -0.005(3) -0.027(3) 0.007(2) O12 0.041(3) 0.0373(17) 0.0353(18) -0.0037(14) -0.0206(18) -0.0084(17) O11 0.038(3) 0.059(2) 0.0342(19) -0.0006(17) -0.0132(18) -0.005(2) O1 0.026(2) 0.0238(15) 0.0353(18) -0.0101(13) -0.0074(17) 0.0003(15) C4 0.025(3) 0.036(2) 0.037(3) -0.023(2) -0.007(2) 0.006(2) O3 0.032(2) 0.0339(17) 0.0413(19) -0.0166(14) -0.0133(17) 0.0091(16) N8 0.020(3) 0.0192(16) 0.0203(17) -0.0084(13) -0.0115(17) 0.0060(16) C20 0.043(4) 0.043(3) 0.0124(19) -0.0062(18) -0.005(2) -0.001(3) C22 0.019(3) 0.041(3) 0.033(3) -0.015(2) -0.008(2) -0.008(2) N10 0.065(4) 0.0220(18) 0.031(2) -0.0090(15) -0.023(2) -0.002(2) O7 0.037(3) 0.101(4) 0.086(4) -0.059(3) -0.011(3) -0.014(3) O10 0.043(3) 0.139(5) 0.0233(19) -0.021(2) 0.002(2) 0.021(3) O8 0.093(6) 0.113(5) 0.070(4) -0.057(3) 0.020(4) -0.042(4) O9 0.064(6) 0.136(7) 0.151(7) 0.019(6) -0.038(5) 0.004(5) C11 0.022(3) 0.0204(19) 0.023(2) -0.0088(16) -0.014(2) 0.0048(19) C1 0.021(3) 0.026(2) 0.0179(19) -0.0076(16) -0.0065(19) 0.0069(19) C8 0.024(3) 0.027(2) 0.021(2) -0.0059(17) -0.006(2) -0.002(2) O4 0.049(3) 0.0233(15) 0.049(2) -0.0064(14) -0.0013(19) 0.0076(16) N6 0.024(3) 0.0298(18) 0.0172(17) -0.0095(14) -0.0090(17) -0.0043(18) C19 0.018(3) 0.033(2) 0.023(2) -0.0136(18) -0.007(2) 0.004(2) C12 0.017(3) 0.0193(18) 0.0177(19) -0.0080(15) -0.0051(19) 0.0023(18) N2 0.013(2) 0.0216(16) 0.0236(18) -0.0063(14) -0.0103(17) 0.0034(15) N1 0.018(3) 0.0301(19) 0.0210(18) -0.0111(15) -0.0057(17) -0.0006(18) C2 0.023(3) 0.045(3) 0.031(2) -0.023(2) -0.006(2) 0.011(2) C3 0.014(3) 0.032(2) 0.026(2) -0.0095(18) -0.008(2) 0.013(2) C5 0.033(4) 0.061(3) 0.065(4) -0.039(3) -0.040(3) 0.028(3) N4 0.017(3) 0.0320(19) 0.0187(18) -0.0117(15) -0.0041(17) -0.0006(17) N3 0.012(2) 0.0240(17) 0.0258(19) -0.0093(15) -0.0098(17) 0.0082(16) C6 0.019(3) 0.026(2) 0.026(2) -0.0067(17) -0.008(2) -0.001(2) C9 0.024(3) 0.035(2) 0.031(2) -0.009(2) -0.005(2) -0.002(2) C7 0.012(3) 0.040(3) 0.030(2) -0.011(2) -0.001(2) -0.006(2) C10 0.041(4) 0.080(4) 0.016(2) -0.010(2) -0.012(2) -0.012(3) N5 0.028(3) 0.0295(19) 0.044(2) -0.0170(17) -0.023(2) 0.0045(18) C13 0.031(3) 0.025(2) 0.041(3) -0.0194(18) -0.012(2) 0.001(2) C14 0.031(3) 0.0190(18) 0.035(2) -0.0065(17) -0.011(2) -0.0026(19) C15 0.077(6) 0.035(3) 0.062(4) -0.006(3) 0.018(4) -0.007(3) C16 0.039(4) 0.033(2) 0.053(3) -0.024(2) -0.015(3) 0.002(2) C17 0.070(5) 0.045(3) 0.039(3) -0.015(2) -0.019(3) -0.005(3) C18 0.096(8) 0.037(3) 0.067(4) -0.008(3) -0.021(5) 0.029(4) N9 0.014(2) 0.0320(18) 0.0200(17) -0.0149(15) -0.0086(16) 0.0087(17) C29 0.016(3) 0.0205(18) 0.0201(19) -0.0078(16) -0.0049(19) 0.0005(18) N7 0.019(3) 0.0227(16) 0.0210(18) -0.0060(14) -0.0109(17) 0.0037(16) C21 0.027(3) 0.044(3) 0.0138(19) -0.0122(18) -0.004(2) 0.001(2) C23 0.035(4) 0.065(4) 0.031(3) -0.010(2) -0.014(3) -0.008(3) C30 0.023(3) 0.025(2) 0.034(2) -0.0119(18) -0.012(2) 0.002(2) C31 0.111(7) 0.024(2) 0.034(3) -0.0060(19) -0.031(4) -0.006(3) C34 0.081(6) 0.038(3) 0.075(5) -0.010(3) -0.021(4) -0.006(3) C35 0.068(6) 0.077(5) 0.053(4) 0.014(4) -0.023(4) -0.047(5) C33 0.168(12) 0.043(3) 0.061(4) -0.010(3) -0.007(6) 0.062(5) O2 0.029(2) 0.0216(14) 0.0194(14) -0.0032(11) -0.0174(15) 0.0027(14) C26 0.023(3) 0.033(2) 0.040(3) -0.012(2) -0.020(2) 0.003(2) C25 0.018(3) 0.032(2) 0.035(2) -0.0124(19) -0.016(2) 0.015(2) C24 0.020(3) 0.023(2) 0.034(2) -0.0119(18) -0.008(2) 0.001(2) C27 0.035(4) 0.033(2) 0.030(2) -0.0168(19) -0.017(2) 0.014(2) C28 0.026(4) 0.050(3) 0.035(3) -0.020(2) -0.018(3) 0.018(3) C37 0.064(6) 0.090(5) 0.035(3) -0.012(3) -0.007(3) -0.015(4) C36 0.189(15) 0.063(5) 0.101(7) -0.023(5) -0.042(8) -0.047(7) O5 0.080(5) 0.054(3) 0.055(3) -0.016(2) -0.027(3) 0.018(3) C32 0.084(6) 0.033(3) 0.060(4) -0.019(3) -0.025(4) 0.012(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 N8 2.011(5) . ? Cu1 N1 2.014(5) . ? Cu1 N3 2.033(4) . ? Cu1 N6 2.044(4) . ? Cu1 O1 2.338(3) . ? Cu1 O2 2.340(3) . ? Cl2 O13 1.413(4) . ? Cl2 O11 1.434(4) . ? Cl2 O12 1.440(4) . ? Cl2 O14 1.443(6) . ? O6 C32 1.372(8) . ? O6 C33 1.462(9) . ? Cl1 O8 1.400(6) . ? Cl1 O9 1.404(10) . ? Cl1 O10 1.425(5) . ? Cl1 O7 1.452(5) . ? Cl4 C37 1.743(8) . ? Cl3 C37 1.762(8) . ? S1 C17 1.738(9) . ? S1 C18 1.774(7) . ? S2 C36 1.699(13) . ? S2 C35 1.815(7) . ? O1 C12 1.178(6) . ? C4 C1 1.501(7) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? O3 C14 1.177(6) . ? N8 C24 1.346(6) . ? N8 N9 1.360(6) . ? C20 C21 1.335(9) . ? C20 C19 1.417(7) . ? C20 H20 0.9300 . ? C22 C19 1.500(8) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? N10 C30 1.310(6) . ? N10 C31 1.488(7) . ? C11 N4 1.436(7) . ? C11 N2 1.461(6) . ? C11 C12 1.570(6) . ? C11 H11 0.9800 . ? C1 N1 1.361(7) . ? C1 C2 1.394(9) . ? C8 N4 1.380(6) . ? C8 C7 1.399(8) . ? C8 C10 1.491(8) . ? O4 C14 1.377(6) . ? O4 C15 1.419(8) . ? N6 C19 1.334(7) . ? N6 N7 1.358(6) . ? C12 N5 1.355(6) . ? N2 C3 1.347(7) . ? N2 N1 1.391(6) . ? C2 C3 1.397(7) . ? C2 H2 0.9300 . ? C3 C5 1.518(8) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? N4 N3 1.377(6) . ? N3 C6 1.331(6) . ? C6 C7 1.404(7) . ? C6 C9 1.502(8) . ? C9 H9B 0.9600 . ? C9 H9A 0.9600 . ? C9 H9C 0.9600 . ? C7 H7 0.9300 . ? C10 H10C 0.9600 . ? C10 H10B 0.9600 . ? C10 H10A 0.9600 . ? N5 C13 1.458(6) . ? C13 C14 1.528(7) . ? C13 C16 1.559(6) . ? C13 H13 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.552(9) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N9 C26 1.349(8) . ? N9 C29 1.462(6) . ? C29 N7 1.457(7) . ? C29 C30 1.529(6) . ? C29 H29 0.9800 . ? N7 C21 1.357(6) . ? C21 C23 1.491(8) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C30 O2 1.273(6) . ? C31 C34 1.502(11) . ? C31 C32 1.529(9) . ? C31 H31 0.9800 . ? C34 C35 1.550(12) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C26 C25 1.369(8) . ? C26 C28 1.492(8) . ? C25 C24 1.388(8) . ? C25 H25 0.9300 . ? C24 C27 1.510(7) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? O5 C32 1.179(8) . ? 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 N8 Cu1 N1 178.22(18) . . ? N8 Cu1 N3 94.58(16) . . ? N1 Cu1 N3 87.06(16) . . ? N8 Cu1 N6 85.25(17) . . ? N1 Cu1 N6 93.10(18) . . ? N3 Cu1 N6 179.35(19) . . ? N8 Cu1 O1 96.40(15) . . ? N1 Cu1 O1 84.47(15) . . ? N3 Cu1 O1 82.96(14) . . ? N6 Cu1 O1 97.68(13) . . ? N8 Cu1 O2 84.93(14) . . ? N1 Cu1 O2 94.27(14) . . ? N3 Cu1 O2 94.38(13) . . ? N6 Cu1 O2 84.97(13) . . ? O1 Cu1 O2 177.11(14) . . ? O13 Cl2 O11 108.1(3) . . ? O13 Cl2 O12 109.8(3) . . ? O11 Cl2 O12 108.7(3) . . ? O13 Cl2 O14 109.3(4) . . ? O11 Cl2 O14 112.5(3) . . ? O12 Cl2 O14 108.3(3) . . ? C32 O6 C33 114.0(6) . . ? O8 Cl1 O9 107.5(6) . . ? O8 Cl1 O10 112.0(4) . . ? O9 Cl1 O10 109.5(5) . . ? O8 Cl1 O7 106.7(4) . . ? O9 Cl1 O7 111.6(5) . . ? O10 Cl1 O7 109.5(4) . . ? C17 S1 C18 103.6(4) . . ? C36 S2 C35 101.7(6) . . ? C12 O1 Cu1 116.1(3) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C24 N8 N9 105.0(4) . . ? C24 N8 Cu1 136.4(4) . . ? N9 N8 Cu1 118.3(3) . . ? C21 C20 C19 106.7(4) . . ? C21 C20 H20 126.7 . . ? C19 C20 H20 126.7 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C30 N10 C31 121.1(5) . . ? N4 C11 N2 112.3(4) . . ? N4 C11 C12 110.0(4) . . ? N2 C11 C12 108.7(3) . . ? N4 C11 H11 108.6 . . ? N2 C11 H11 108.6 . . ? C12 C11 H11 108.6 . . ? N1 C1 C2 110.7(4) . . ? N1 C1 C4 121.3(5) . . ? C2 C1 C4 128.0(5) . . ? N4 C8 C7 104.8(5) . . ? N4 C8 C10 123.9(5) . . ? C7 C8 C10 131.3(5) . . ? C14 O4 C15 113.7(5) . . ? C19 N6 N7 105.9(4) . . ? C19 N6 Cu1 135.3(3) . . ? N7 N6 Cu1 118.1(3) . . ? N6 C19 C20 109.1(5) . . ? N6 C19 C22 123.2(4) . . ? C20 C19 C22 127.6(5) . . ? O1 C12 N5 125.8(4) . . ? O1 C12 C11 120.6(4) . . ? N5 C12 C11 113.6(4) . . ? C3 N2 N1 112.9(4) . . ? C3 N2 C11 128.8(4) . . ? N1 N2 C11 117.7(4) . . ? C1 N1 N2 103.8(4) . . ? C1 N1 Cu1 136.8(4) . . ? N2 N1 Cu1 119.3(3) . . ? C1 C2 C3 106.8(5) . . ? C1 C2 H2 126.6 . . ? C3 C2 H2 126.6 . . ? N2 C3 C2 105.8(5) . . ? N2 C3 C5 123.6(5) . . ? C2 C3 C5 130.5(5) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N3 N4 C8 112.0(4) . . ? N3 N4 C11 119.7(4) . . ? C8 N4 C11 128.1(4) . . ? C6 N3 N4 105.3(4) . . ? C6 N3 Cu1 136.0(4) . . ? N4 N3 Cu1 118.1(3) . . ? N3 C6 C7 111.2(5) . . ? N3 C6 C9 122.4(4) . . ? C7 C6 C9 126.4(4) . . ? C6 C9 H9B 109.5 . . ? C6 C9 H9A 109.5 . . ? H9B C9 H9A 109.5 . . ? C6 C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? C8 C7 C6 106.6(4) . . ? C8 C7 H7 126.7 . . ? C6 C7 H7 126.7 . . ? C8 C10 H10C 109.5 . . ? C8 C10 H10B 109.5 . . ? H10C C10 H10B 109.5 . . ? C8 C10 H10A 109.5 . . ? H10C C10 H10A 109.5 . . ? H10B C10 H10A 109.5 . . ? C12 N5 C13 120.0(4) . . ? N5 C13 C14 108.6(4) . . ? N5 C13 C16 109.0(4) . . ? C14 C13 C16 110.8(4) . . ? N5 C13 H13 109.5 . . ? C14 C13 H13 109.5 . . ? C16 C13 H13 109.5 . . ? O3 C14 O4 125.2(5) . . ? O3 C14 C13 126.4(4) . . ? O4 C14 C13 108.4(4) . . ? O4 C15 H15A 109.5 . . ? O4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C13 112.8(5) . . ? C17 C16 H16A 109.0 . . ? C13 C16 H16A 109.0 . . ? C17 C16 H16B 109.0 . . ? C13 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 C17 S1 115.4(5) . . ? C16 C17 H17A 108.4 . . ? S1 C17 H17A 108.4 . . ? C16 C17 H17B 108.4 . . ? S1 C17 H17B 108.4 . . ? H17A C17 H17B 107.5 . . ? S1 C18 H18A 109.5 . . ? S1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? S1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C26 N9 N8 111.7(4) . . ? C26 N9 C29 127.3(4) . . ? N8 N9 C29 120.5(4) . . ? N7 C29 N9 108.5(3) . . ? N7 C29 C30 110.9(4) . . ? N9 C29 C30 110.3(4) . . ? N7 C29 H29 109.0 . . ? N9 C29 H29 109.0 . . ? C30 C29 H29 109.0 . . ? C21 N7 N6 110.9(4) . . ? C21 N7 C29 128.7(4) . . ? N6 N7 C29 120.4(4) . . ? C20 C21 N7 107.4(5) . . ? C20 C21 C23 130.1(5) . . ? N7 C21 C23 122.4(5) . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O2 C30 N10 122.9(4) . . ? O2 C30 C29 119.7(4) . . ? N10 C30 C29 117.3(5) . . ? N10 C31 C34 113.8(7) . . ? N10 C31 C32 107.4(4) . . ? C34 C31 C32 110.8(5) . . ? N10 C31 H31 108.2 . . ? C34 C31 H31 108.2 . . ? C32 C31 H31 108.2 . . ? C31 C34 C35 110.3(5) . . ? C31 C34 H34A 109.6 . . ? C35 C34 H34A 109.6 . . ? C31 C34 H34B 109.6 . . ? C35 C34 H34B 109.6 . . ? H34A C34 H34B 108.1 . . ? C34 C35 S2 112.0(5) . . ? C34 C35 H35A 109.2 . . ? S2 C35 H35A 109.2 . . ? C34 C35 H35B 109.2 . . ? S2 C35 H35B 109.2 . . ? H35A C35 H35B 107.9 . . ? O6 C33 H33A 109.5 . . ? O6 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O6 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C30 O2 Cu1 114.3(3) . . ? N9 C26 C25 106.5(5) . . ? N9 C26 C28 122.9(5) . . ? C25 C26 C28 130.5(6) . . ? C26 C25 C24 106.4(5) . . ? C26 C25 H25 126.8 . . ? C24 C25 H25 126.8 . . ? N8 C24 C25 110.3(4) . . ? N8 C24 C27 121.0(5) . . ? C25 C24 C27 128.7(5) . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? Cl4 C37 Cl3 109.3(4) . . ? Cl4 C37 H37A 109.8 . . ? Cl3 C37 H37A 109.8 . . ? Cl4 C37 H37B 109.8 . . ? Cl3 C37 H37B 109.8 . . ? H37A C37 H37B 108.3 . . ? S2 C36 H36A 109.5 . . ? S2 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? S2 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O5 C32 O6 122.5(6) . . ? O5 C32 C31 127.0(6) . . ? O6 C32 C31 110.2(5) . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.038 0.673 0.691 321.5 -3.5 _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 1.705 _refine_diff_density_min -0.568 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 916435'