# 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_90930cm _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H9 Cl Cu N2 O2' _chemical_formula_sum 'C12 H9 Cl Cu N2 O2' _chemical_formula_weight 312.20 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 9.9668(17) _cell_length_b 11.5475(19) _cell_length_c 15.479(2) _cell_angle_alpha 82.766(2) _cell_angle_beta 82.656(3) _cell_angle_gamma 74.840(2) _cell_volume 1697.4(5) _cell_formula_units_Z 6 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2430 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 25.08 _exptl_crystal_description prism _exptl_crystal_colour purple _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.832 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 942 _exptl_absorpt_coefficient_mu 2.158 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5832 _exptl_absorpt_correction_T_max 0.6481 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9268 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6513 _reflns_number_gt 4819 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0800P)^2^+1.9900P] 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 6513 _refine_ls_number_parameters 475 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0729 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1417 _refine_ls_wR_factor_gt 0.1355 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 C1 C 0.8213(6) -0.1580(5) 0.1596(4) 0.0417(12) Uani 1 1 d . . . C2 C 0.6806(7) -0.1365(6) 0.1334(4) 0.0523(15) Uani 1 1 d . . . H2 H 0.6341 -0.1977 0.1458 0.063 Uiso 1 1 calc R . . C3 C 0.6159(5) -0.0307(6) 0.0916(4) 0.0430(13) Uani 1 1 d . . . H3 H 0.5234 -0.0158 0.0798 0.052 Uiso 1 1 calc R . . C4 C 0.6941(5) 0.0575(5) 0.0663(3) 0.0387(12) Uani 1 1 d . . . C5 C 0.6386(7) 0.1676(6) 0.0173(4) 0.0535(16) Uani 1 1 d . . . H5 H 0.5479 0.1835 0.0019 0.064 Uiso 1 1 calc R . . C6 C 0.7140(6) 0.2512(5) -0.0083(4) 0.0478(14) Uani 1 1 d . . . H6 H 0.6766 0.3215 -0.0426 0.057 Uiso 1 1 calc R . . C7 C 0.8525(6) 0.2291(5) 0.0186(4) 0.0437(12) Uani 1 1 d . . . C8 C 0.9346(7) 0.3135(5) -0.0004(4) 0.0481(14) Uani 1 1 d . . . H8 H 0.9006 0.3886 -0.0301 0.058 Uiso 1 1 calc R . . C9 C 1.0705(7) 0.2797(6) 0.0273(4) 0.0536(15) Uani 1 1 d . . . H9 H 1.1300 0.3305 0.0116 0.064 Uiso 1 1 calc R . . C10 C 1.1148(6) 0.1738(5) 0.0767(3) 0.0416(12) Uani 1 1 d . . . H10 H 1.2029 0.1565 0.0964 0.050 Uiso 1 1 calc R . . C11 C 0.9088(5) 0.1201(4) 0.0684(3) 0.0295(9) Uani 1 1 d . . . C12 C 0.8280(5) 0.0377(5) 0.0917(3) 0.0323(10) Uani 1 1 d . . . C13 C 0.9608(5) 0.2689(4) 0.2774(3) 0.0292(10) Uani 1 1 d . . . C14 C 1.0038(6) 0.1569(5) 0.3283(4) 0.0424(12) Uani 1 1 d . . . H14 H 1.0896 0.1374 0.3512 0.051 Uiso 1 1 calc R . . C15 C 0.9236(6) 0.0798(4) 0.3435(3) 0.0409(12) Uani 1 1 d . . . H15 H 0.9565 0.0053 0.3743 0.049 Uiso 1 1 calc R . . C16 C 0.7881(3) 0.1086(2) 0.3139(2) 0.0333(10) Uani 1 1 d G . . C17 C 0.6959(4) 0.0349(2) 0.3318(2) 0.0450(13) Uani 1 1 d G . . H17 H 0.7218 -0.0394 0.3643 0.054 Uiso 1 1 calc R . . C18 C 0.5648(3) 0.0722(3) 0.3010(2) 0.0474(14) Uani 1 1 d G . . H18 H 0.5030 0.0229 0.3130 0.057 Uiso 1 1 calc R . . C19 C 0.5259(2) 0.1833(3) 0.2524(2) 0.0328(10) Uani 1 1 d G . . C23 C 0.6182(3) 0.2570(2) 0.23453(18) 0.0272(9) Uani 1 1 d G . . C24 C 0.7493(3) 0.2197(2) 0.26526(19) 0.0230(8) Uani 1 1 d G . . C20 C 0.3922(6) 0.2299(6) 0.2220(3) 0.0428(13) Uani 1 1 d . . . H20 H 0.3247 0.1863 0.2362 0.051 Uiso 1 1 calc R . . C21 C 0.3609(6) 0.3390(6) 0.1716(4) 0.0471(14) Uani 1 1 d . . . H21 H 0.2749 0.3679 0.1491 0.057 Uiso 1 1 calc R . . C22 C 0.4641(5) 0.4056(5) 0.1553(3) 0.0373(11) Uani 1 1 d . . . H22 H 0.4429 0.4800 0.1225 0.045 Uiso 1 1 calc R . . C25 C 0.3958(5) 0.5770(4) 0.3211(3) 0.0337(10) Uani 1 1 d . . . C26 C 0.4842(6) 0.6597(5) 0.2982(3) 0.0382(11) Uani 1 1 d . . . H26 H 0.4529 0.7303 0.2625 0.046 Uiso 1 1 calc R . . C27 C 0.6101(5) 0.6369(4) 0.3275(3) 0.0356(11) Uani 1 1 d . . . H27 H 0.6657 0.6908 0.3111 0.043 Uiso 1 1 calc R . . C28 C 0.6595(5) 0.5303(4) 0.3836(3) 0.0300(10) Uani 1 1 d . . . C29 C 0.7925(5) 0.4989(5) 0.4174(4) 0.0433(12) Uani 1 1 d . . . H29 H 0.8504 0.5514 0.4046 0.052 Uiso 1 1 calc R . . C30 C 0.8354(5) 0.3949(5) 0.4675(4) 0.0450(13) Uani 1 1 d . . . H30 H 0.9226 0.3759 0.4886 0.054 Uiso 1 1 calc R . . C31 C 0.7492(5) 0.3149(5) 0.4880(4) 0.0401(12) Uani 1 1 d . . . C32 C 0.7831(6) 0.2011(6) 0.5416(4) 0.0502(15) Uani 1 1 d . . . H32 H 0.8661 0.1784 0.5679 0.060 Uiso 1 1 calc R . . C33 C 0.6995(7) 0.1307(5) 0.5534(4) 0.0490(15) Uani 1 1 d . . . H33 H 0.7256 0.0567 0.5863 0.059 Uiso 1 1 calc R . . C34 C 0.5693(6) 0.1627(4) 0.5179(4) 0.0433(12) Uani 1 1 d . . . H34 H 0.5129 0.1087 0.5259 0.052 Uiso 1 1 calc R . . C35 C 0.6179(5) 0.3416(4) 0.4547(3) 0.0263(9) Uani 1 1 d . . . C36 C 0.5726(5) 0.4536(4) 0.4030(3) 0.0274(9) Uani 1 1 d . . . Cl1 Cl 1.28424(15) -0.05110(15) 0.20044(11) 0.0543(4) Uani 1 1 d . . . Cl2 Cl 0.64999(15) 0.58406(13) 0.06402(10) 0.0485(3) Uani 1 1 d . . . Cl3 Cl 0.24896(18) 0.19398(15) 0.47640(12) 0.0624(5) Uani 1 1 d . . . Cu1 Cu 1.07623(7) -0.06299(6) 0.17058(5) 0.03953(18) Uani 1 1 d . . . Cu2 Cu 0.74468(6) 0.44464(5) 0.16722(4) 0.02683(15) Uani 1 1 d . . . Cu3 Cu 0.34726(6) 0.34307(5) 0.42098(4) 0.03034(16) Uani 1 1 d . . . N1 N 0.8876(4) -0.0690(4) 0.1371(3) 0.0326(9) Uani 1 1 d . . . N2 N 1.0379(4) 0.0925(4) 0.0986(3) 0.0348(9) Uani 1 1 d . . . N3 N 0.8340(4) 0.2994(3) 0.2456(2) 0.0289(8) Uani 1 1 d . . . N4 N 0.5886(4) 0.3673(3) 0.1843(2) 0.0278(8) Uani 1 1 d . . . N5 N 0.4428(4) 0.4748(3) 0.3735(2) 0.0273(8) Uani 1 1 d . . . N6 N 0.5265(4) 0.2710(4) 0.4726(3) 0.0328(9) Uani 1 1 d . . . O1 O 0.8792(4) -0.2576(3) 0.2060(3) 0.0579(12) Uani 1 1 d . . . H1X H 0.9538 -0.2499 0.2232 0.069 Uiso 1 1 d R . . O2 O 1.0821(5) -0.2022(4) 0.2527(3) 0.0650(13) Uani 1 1 d . . . H2X H 1.1616 -0.2521 0.2539 0.078 Uiso 1 1 d R . . O3 O 1.0387(3) 0.3436(3) 0.2587(2) 0.0397(8) Uani 1 1 d . . . H3X H 0.9963 0.4053 0.2278 0.048 Uiso 1 1 d R . . O4 O 0.9015(4) 0.5157(3) 0.1654(3) 0.0434(9) Uani 1 1 d . . . H4X H 0.8706 0.5905 0.1713 0.052 Uiso 1 1 d R . . O5 O 0.2786(4) 0.6012(3) 0.2944(3) 0.0467(10) Uani 1 1 d . . . H5X H 0.2344 0.5505 0.3196 0.056 Uiso 1 1 d R . . O6 O 0.1782(4) 0.4276(3) 0.3723(3) 0.0419(9) Uani 1 1 d . . . H6X H 0.1564 0.3826 0.3398 0.050 Uiso 1 1 d 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 C1 0.046(3) 0.043(3) 0.044(3) -0.012(2) -0.006(2) -0.021(2) C2 0.053(3) 0.057(4) 0.054(3) 0.002(3) -0.014(3) -0.026(3) C3 0.031(2) 0.062(4) 0.044(3) -0.012(3) -0.009(2) -0.019(2) C4 0.036(3) 0.044(3) 0.039(3) -0.016(2) -0.009(2) -0.006(2) C5 0.054(3) 0.052(4) 0.049(3) -0.001(3) -0.026(3) 0.006(3) C6 0.055(3) 0.042(3) 0.039(3) 0.006(2) -0.013(3) 0.000(3) C7 0.056(3) 0.031(3) 0.040(3) 0.001(2) -0.010(2) -0.005(2) C8 0.074(4) 0.029(3) 0.039(3) 0.006(2) -0.002(3) -0.015(3) C9 0.063(4) 0.053(4) 0.047(3) -0.001(3) 0.002(3) -0.023(3) C10 0.045(3) 0.042(3) 0.040(3) -0.003(2) 0.001(2) -0.018(2) C11 0.037(2) 0.024(2) 0.025(2) -0.0089(18) 0.0015(18) -0.0029(18) C12 0.032(2) 0.038(3) 0.028(2) -0.014(2) -0.0029(19) -0.006(2) C13 0.027(2) 0.039(3) 0.021(2) -0.0076(19) -0.0030(17) -0.006(2) C14 0.035(3) 0.038(3) 0.048(3) 0.004(2) -0.003(2) -0.002(2) C15 0.054(3) 0.024(2) 0.040(3) 0.001(2) -0.013(2) 0.003(2) C16 0.049(3) 0.020(2) 0.029(2) -0.0028(18) -0.005(2) -0.004(2) C17 0.071(4) 0.028(3) 0.036(3) 0.004(2) 0.001(3) -0.019(3) C18 0.067(4) 0.039(3) 0.046(3) 0.005(2) -0.005(3) -0.035(3) C19 0.035(2) 0.047(3) 0.024(2) -0.013(2) 0.0091(18) -0.024(2) C23 0.028(2) 0.025(2) 0.026(2) 0.0006(18) 0.0039(17) -0.0084(18) C24 0.026(2) 0.022(2) 0.022(2) -0.0057(16) -0.0015(16) -0.0059(16) C20 0.041(3) 0.061(4) 0.037(3) -0.004(3) 0.002(2) -0.035(3) C21 0.041(3) 0.072(4) 0.039(3) -0.005(3) -0.011(2) -0.030(3) C22 0.030(2) 0.041(3) 0.042(3) -0.001(2) -0.009(2) -0.009(2) C25 0.033(2) 0.025(2) 0.041(3) 0.005(2) -0.007(2) -0.0060(19) C26 0.046(3) 0.032(3) 0.035(3) 0.002(2) 0.001(2) -0.013(2) C27 0.042(3) 0.030(2) 0.040(3) -0.002(2) -0.004(2) -0.018(2) C28 0.026(2) 0.027(2) 0.038(3) -0.0071(19) -0.0006(19) -0.0075(18) C29 0.031(3) 0.050(3) 0.051(3) -0.012(3) -0.008(2) -0.008(2) C30 0.027(2) 0.056(3) 0.053(3) -0.019(3) -0.009(2) -0.003(2) C31 0.030(2) 0.035(3) 0.048(3) -0.014(2) -0.007(2) 0.010(2) C32 0.051(3) 0.051(3) 0.044(3) 0.002(3) -0.026(3) 0.000(3) C33 0.061(4) 0.032(3) 0.040(3) 0.000(2) -0.014(3) 0.016(3) C34 0.064(4) 0.019(2) 0.046(3) 0.003(2) -0.014(3) -0.007(2) C35 0.032(2) 0.021(2) 0.023(2) -0.0033(17) -0.0023(17) -0.0018(18) C36 0.029(2) 0.030(2) 0.023(2) -0.0051(18) -0.0055(17) -0.0032(18) Cl1 0.0398(7) 0.0558(9) 0.0735(10) -0.0042(7) -0.0156(7) -0.0190(6) Cl2 0.0453(7) 0.0441(7) 0.0545(8) 0.0216(6) -0.0148(6) -0.0160(6) Cl3 0.0704(10) 0.0529(9) 0.0748(11) 0.0258(8) -0.0302(8) -0.0388(8) Cu1 0.0367(3) 0.0346(3) 0.0486(4) 0.0024(3) -0.0100(3) -0.0114(3) Cu2 0.0286(3) 0.0261(3) 0.0292(3) 0.0021(2) -0.0073(2) -0.0131(2) Cu3 0.0357(3) 0.0268(3) 0.0311(3) 0.0003(2) -0.0092(2) -0.0108(2) N1 0.037(2) 0.029(2) 0.036(2) -0.0113(17) -0.0015(17) -0.0134(17) N2 0.034(2) 0.034(2) 0.037(2) -0.0066(18) 0.0005(17) -0.0102(17) N3 0.032(2) 0.030(2) 0.0267(19) -0.0019(16) -0.0010(15) -0.0123(16) N4 0.0309(19) 0.0270(19) 0.0291(19) 0.0011(16) -0.0095(15) -0.0123(16) N5 0.0324(19) 0.0260(19) 0.0252(18) -0.0005(15) -0.0089(15) -0.0084(16) N6 0.037(2) 0.029(2) 0.029(2) 0.0001(16) -0.0052(17) -0.0043(17) O1 0.048(2) 0.0251(19) 0.101(4) 0.000(2) 0.003(2) -0.0175(17) O2 0.057(3) 0.055(3) 0.083(3) 0.031(2) -0.028(2) -0.022(2) O3 0.0266(16) 0.042(2) 0.054(2) -0.0011(17) -0.0135(15) -0.0117(15) O4 0.0374(19) 0.035(2) 0.064(2) 0.0018(18) -0.0098(17) -0.0206(16) O5 0.044(2) 0.036(2) 0.062(3) 0.0127(18) -0.0279(19) -0.0105(17) O6 0.043(2) 0.037(2) 0.052(2) 0.0014(17) -0.0182(17) -0.0175(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.313(7) . ? C1 N1 1.350(7) . ? C1 C2 1.459(8) . ? C2 C3 1.350(9) . ? C2 H2 0.9300 . ? C3 C4 1.427(8) . ? C3 H3 0.9300 . ? C4 C12 1.392(7) . ? C4 C5 1.412(8) . ? C5 C6 1.364(9) . ? C5 H5 0.9300 . ? C6 C7 1.442(8) . ? C6 H6 0.9300 . ? C7 C8 1.410(8) . ? C7 C11 1.412(7) . ? C8 C9 1.415(9) . ? C8 H8 0.9300 . ? C9 C10 1.357(8) . ? C9 H9 0.9300 . ? C10 N2 1.347(7) . ? C10 H10 0.9300 . ? C11 N2 1.370(6) . ? C11 C12 1.387(7) . ? C12 N1 1.368(7) . ? C13 O3 1.289(6) . ? C13 N3 1.358(6) . ? C13 C14 1.420(7) . ? C14 C15 1.327(8) . ? C14 H14 0.9300 . ? C15 C16 1.424(6) . ? C15 H15 0.9300 . ? C16 C17 1.3900 . ? C16 C24 1.3900 . ? C17 C18 1.3900 . ? C17 H17 0.9300 . ? C18 C19 1.3900 . ? C18 H18 0.9300 . ? C19 C23 1.3900 . ? C19 C20 1.418(6) . ? C23 N4 1.388(4) . ? C23 C24 1.3900 . ? C24 N3 1.387(4) . ? C20 C21 1.379(9) . ? C20 H20 0.9300 . ? C21 C22 1.418(7) . ? C21 H21 0.9300 . ? C22 N4 1.320(6) . ? C22 H22 0.9300 . ? C25 O5 1.240(6) . ? C25 N5 1.356(6) . ? C25 C26 1.445(7) . ? C26 C27 1.338(7) . ? C26 H26 0.9300 . ? C27 C28 1.426(7) . ? C27 H27 0.9300 . ? C28 C36 1.376(7) . ? C28 C29 1.428(7) . ? C29 C30 1.345(8) . ? C29 H29 0.9300 . ? C30 C31 1.401(8) . ? C30 H30 0.9300 . ? C31 C35 1.413(7) . ? C31 C32 1.447(8) . ? C32 C33 1.291(9) . ? C32 H32 0.9300 . ? C33 C34 1.416(8) . ? C33 H33 0.9300 . ? C34 N6 1.347(6) . ? C34 H34 0.9300 . ? C35 N6 1.355(6) . ? C35 C36 1.429(6) . ? C36 N5 1.379(6) . ? Cl1 Cu1 2.2227(15) . ? Cl2 Cu2 2.2310(14) . ? Cl3 Cu3 2.2260(15) . ? Cu1 O2 1.913(4) . ? Cu1 N2 1.964(4) . ? Cu1 N1 2.033(4) . ? Cu2 O4 1.941(3) . ? Cu2 N4 1.962(4) . ? Cu2 N3 2.015(4) . ? Cu3 O6 1.908(4) . ? Cu3 N6 1.986(4) . ? Cu3 N5 2.014(4) . ? O1 H1X 0.8500 . ? O2 H2X 0.8500 . ? O3 H3X 0.8500 . ? O4 H4X 0.8500 . ? O5 H5X 0.8500 . ? O6 H6X 0.8500 . ? 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 C1 N1 121.1(5) . . ? O1 C1 C2 121.6(5) . . ? N1 C1 C2 117.2(5) . . ? C3 C2 C1 122.1(5) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C2 C3 C4 117.7(5) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C12 C4 C5 118.0(5) . . ? C12 C4 C3 120.1(5) . . ? C5 C4 C3 121.9(5) . . ? C6 C5 C4 122.0(5) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C7 119.2(5) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C8 C7 C11 117.5(5) . . ? C8 C7 C6 123.0(5) . . ? C11 C7 C6 119.4(5) . . ? C7 C8 C9 117.6(5) . . ? C7 C8 H8 121.2 . . ? C9 C8 H8 121.2 . . ? C10 C9 C8 120.6(6) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? N2 C10 C9 123.4(5) . . ? N2 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? N2 C11 C12 117.5(4) . . ? N2 C11 C7 123.6(5) . . ? C12 C11 C7 118.8(5) . . ? N1 C12 C11 117.4(4) . . ? N1 C12 C4 120.1(5) . . ? C11 C12 C4 122.5(5) . . ? O3 C13 N3 117.8(4) . . ? O3 C13 C14 122.4(4) . . ? N3 C13 C14 119.8(4) . . ? C15 C14 C13 121.0(5) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 121.5(4) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C17 C16 C24 120.0 . . ? C17 C16 C15 124.4(3) . . ? C24 C16 C15 115.6(3) . . ? C18 C17 C16 120.0 . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 120.0 . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C23 C19 C18 120.0 . . ? C23 C19 C20 116.6(3) . . ? C18 C19 C20 123.3(3) . . ? N4 C23 C19 123.3(2) . . ? N4 C23 C24 116.7(2) . . ? C19 C23 C24 120.0 . . ? N3 C24 C23 116.3(2) . . ? N3 C24 C16 123.7(2) . . ? C23 C24 C16 120.0 . . ? C21 C20 C19 120.8(4) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C20 C21 C22 117.8(5) . . ? C20 C21 H21 121.1 . . ? C22 C21 H21 121.1 . . ? N4 C22 C21 123.4(5) . . ? N4 C22 H22 118.3 . . ? C21 C22 H22 118.3 . . ? O5 C25 N5 121.3(4) . . ? O5 C25 C26 120.2(4) . . ? N5 C25 C26 118.6(4) . . ? C27 C26 C25 121.4(5) . . ? C27 C26 H26 119.3 . . ? C25 C26 H26 119.3 . . ? C26 C27 C28 120.4(5) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C36 C28 C27 116.3(4) . . ? C36 C28 C29 119.7(5) . . ? C27 C28 C29 124.0(5) . . ? C30 C29 C28 121.3(5) . . ? C30 C29 H29 119.4 . . ? C28 C29 H29 119.4 . . ? C29 C30 C31 120.2(5) . . ? C29 C30 H30 119.9 . . ? C31 C30 H30 119.9 . . ? C30 C31 C35 120.3(5) . . ? C30 C31 C32 125.4(5) . . ? C35 C31 C32 114.3(5) . . ? C33 C32 C31 120.8(5) . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.6 . . ? C32 C33 C34 122.0(5) . . ? C32 C33 H33 119.0 . . ? C34 C33 H33 119.0 . . ? N6 C34 C33 120.3(5) . . ? N6 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? N6 C35 C31 124.4(4) . . ? N6 C35 C36 116.7(4) . . ? C31 C35 C36 118.8(4) . . ? C28 C36 N5 124.4(4) . . ? C28 C36 C35 119.7(4) . . ? N5 C36 C35 115.9(4) . . ? O2 Cu1 N2 169.6(2) . . ? O2 Cu1 N1 91.22(18) . . ? N2 Cu1 N1 83.09(17) . . ? O2 Cu1 Cl1 91.52(14) . . ? N2 Cu1 Cl1 94.37(13) . . ? N1 Cu1 Cl1 177.01(13) . . ? O4 Cu2 N4 173.02(16) . . ? O4 Cu2 N3 92.10(16) . . ? N4 Cu2 N3 82.67(15) . . ? O4 Cu2 Cl2 91.84(12) . . ? N4 Cu2 Cl2 94.04(12) . . ? N3 Cu2 Cl2 170.57(12) . . ? O6 Cu3 N6 174.30(16) . . ? O6 Cu3 N5 92.40(15) . . ? N6 Cu3 N5 82.66(16) . . ? O6 Cu3 Cl3 89.85(12) . . ? N6 Cu3 Cl3 95.08(13) . . ? N5 Cu3 Cl3 177.73(12) . . ? C1 N1 C12 122.6(4) . . ? C1 N1 Cu1 127.6(4) . . ? C12 N1 Cu1 109.7(3) . . ? C10 N2 C11 117.0(4) . . ? C10 N2 Cu1 131.0(4) . . ? C11 N2 Cu1 111.9(3) . . ? C13 N3 C24 118.3(4) . . ? C13 N3 Cu2 130.3(3) . . ? C24 N3 Cu2 111.3(2) . . ? C22 N4 C23 117.9(4) . . ? C22 N4 Cu2 129.3(3) . . ? C23 N4 Cu2 112.9(2) . . ? C25 N5 C36 118.9(4) . . ? C25 N5 Cu3 129.5(3) . . ? C36 N5 Cu3 111.6(3) . . ? C34 N6 C35 117.8(4) . . ? C34 N6 Cu3 129.2(4) . . ? C35 N6 Cu3 113.0(3) . . ? C1 O1 H1X 109.1 . . ? Cu1 O2 H2X 115.1 . . ? C13 O3 H3X 109.5 . . ? Cu2 O4 H4X 109.0 . . ? C25 O5 H5X 109.1 . . ? Cu3 O6 H6X 109.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 174.7(6) . . . . ? N1 C1 C2 C3 -2.7(9) . . . . ? C1 C2 C3 C4 5.6(9) . . . . ? C2 C3 C4 C12 -5.8(8) . . . . ? C2 C3 C4 C5 175.6(6) . . . . ? C12 C4 C5 C6 2.6(9) . . . . ? C3 C4 C5 C6 -178.9(6) . . . . ? C4 C5 C6 C7 -2.6(9) . . . . ? C5 C6 C7 C8 -176.2(6) . . . . ? C5 C6 C7 C11 1.9(8) . . . . ? C11 C7 C8 C9 3.7(8) . . . . ? C6 C7 C8 C9 -178.2(5) . . . . ? C7 C8 C9 C10 -5.3(9) . . . . ? C8 C9 C10 N2 3.4(9) . . . . ? C8 C7 C11 N2 -0.2(8) . . . . ? C6 C7 C11 N2 -178.4(5) . . . . ? C8 C7 C11 C12 177.0(5) . . . . ? C6 C7 C11 C12 -1.2(7) . . . . ? N2 C11 C12 N1 -5.0(6) . . . . ? C7 C11 C12 N1 177.6(4) . . . . ? N2 C11 C12 C4 178.6(4) . . . . ? C7 C11 C12 C4 1.2(7) . . . . ? C5 C4 C12 N1 -178.1(5) . . . . ? C3 C4 C12 N1 3.3(7) . . . . ? C5 C4 C12 C11 -1.8(7) . . . . ? C3 C4 C12 C11 179.6(5) . . . . ? O3 C13 C14 C15 -177.3(5) . . . . ? N3 C13 C14 C15 1.8(8) . . . . ? C13 C14 C15 C16 -3.5(8) . . . . ? C14 C15 C16 C17 -176.3(4) . . . . ? C14 C15 C16 C24 2.6(6) . . . . ? C24 C16 C17 C18 0.0 . . . . ? C15 C16 C17 C18 178.9(4) . . . . ? C16 C17 C18 C19 0.0 . . . . ? C17 C18 C19 C23 0.0 . . . . ? C17 C18 C19 C20 -177.2(4) . . . . ? C18 C19 C23 N4 178.0(3) . . . . ? C20 C19 C23 N4 -4.5(4) . . . . ? C18 C19 C23 C24 0.0 . . . . ? C20 C19 C23 C24 177.4(4) . . . . ? N4 C23 C24 N3 2.8(3) . . . . ? C19 C23 C24 N3 -179.0(3) . . . . ? N4 C23 C24 C16 -178.2(3) . . . . ? C19 C23 C24 C16 0.0 . . . . ? C17 C16 C24 N3 179.0(3) . . . . ? C15 C16 C24 N3 0.0(4) . . . . ? C17 C16 C24 C23 0.0 . . . . ? C15 C16 C24 C23 -179.0(3) . . . . ? C23 C19 C20 C21 4.8(6) . . . . ? C18 C19 C20 C21 -177.9(4) . . . . ? C19 C20 C21 C22 -3.3(8) . . . . ? C20 C21 C22 N4 1.4(9) . . . . ? O5 C25 C26 C27 178.8(5) . . . . ? N5 C25 C26 C27 0.3(8) . . . . ? C25 C26 C27 C28 -1.1(8) . . . . ? C26 C27 C28 C36 1.5(7) . . . . ? C26 C27 C28 C29 179.8(5) . . . . ? C36 C28 C29 C30 0.7(8) . . . . ? C27 C28 C29 C30 -177.5(5) . . . . ? C28 C29 C30 C31 -0.4(8) . . . . ? C29 C30 C31 C35 1.4(8) . . . . ? C29 C30 C31 C32 -179.5(6) . . . . ? C30 C31 C32 C33 -176.7(6) . . . . ? C35 C31 C32 C33 2.5(8) . . . . ? C31 C32 C33 C34 -2.5(9) . . . . ? C32 C33 C34 N6 -2.3(9) . . . . ? C30 C31 C35 N6 -178.5(5) . . . . ? C32 C31 C35 N6 2.2(7) . . . . ? C30 C31 C35 C36 -2.5(7) . . . . ? C32 C31 C35 C36 178.2(4) . . . . ? C27 C28 C36 N5 -1.3(7) . . . . ? C29 C28 C36 N5 -179.7(4) . . . . ? C27 C28 C36 C35 176.4(4) . . . . ? C29 C28 C36 C35 -1.9(7) . . . . ? N6 C35 C36 C28 179.1(4) . . . . ? C31 C35 C36 C28 2.8(7) . . . . ? N6 C35 C36 N5 -2.9(6) . . . . ? C31 C35 C36 N5 -179.2(4) . . . . ? O1 C1 N1 C12 -177.5(5) . . . . ? C2 C1 N1 C12 -0.1(8) . . . . ? O1 C1 N1 Cu1 -2.5(8) . . . . ? C2 C1 N1 Cu1 174.9(4) . . . . ? C11 C12 N1 C1 -176.8(5) . . . . ? C4 C12 N1 C1 -0.3(7) . . . . ? C11 C12 N1 Cu1 7.4(5) . . . . ? C4 C12 N1 Cu1 -176.1(4) . . . . ? O2 Cu1 N1 C1 -10.1(5) . . . . ? N2 Cu1 N1 C1 178.7(4) . . . . ? O2 Cu1 N1 C12 165.4(3) . . . . ? N2 Cu1 N1 C12 -5.8(3) . . . . ? C9 C10 N2 C11 0.3(8) . . . . ? C9 C10 N2 Cu1 -178.3(4) . . . . ? C12 C11 N2 C10 -179.1(4) . . . . ? C7 C11 N2 C10 -1.9(7) . . . . ? C12 C11 N2 Cu1 -0.3(5) . . . . ? C7 C11 N2 Cu1 177.0(4) . . . . ? O2 Cu1 N2 C10 124.6(10) . . . . ? N1 Cu1 N2 C10 -178.0(5) . . . . ? Cl1 Cu1 N2 C10 0.4(5) . . . . ? O2 Cu1 N2 C11 -54.0(12) . . . . ? N1 Cu1 N2 C11 3.4(3) . . . . ? Cl1 Cu1 N2 C11 -178.2(3) . . . . ? O3 C13 N3 C24 179.9(4) . . . . ? C14 C13 N3 C24 0.8(6) . . . . ? O3 C13 N3 Cu2 2.6(6) . . . . ? C14 C13 N3 Cu2 -176.5(4) . . . . ? C23 C24 N3 C13 177.3(3) . . . . ? C16 C24 N3 C13 -1.7(5) . . . . ? C23 C24 N3 Cu2 -4.9(3) . . . . ? C16 C24 N3 Cu2 176.11(18) . . . . ? O4 Cu2 N3 C13 -3.1(4) . . . . ? N4 Cu2 N3 C13 -178.4(4) . . . . ? O4 Cu2 N3 C24 179.5(3) . . . . ? N4 Cu2 N3 C24 4.1(3) . . . . ? C21 C22 N4 C23 -1.1(7) . . . . ? C21 C22 N4 Cu2 179.0(4) . . . . ? C19 C23 N4 C22 2.8(5) . . . . ? C24 C23 N4 C22 -179.1(3) . . . . ? C19 C23 N4 Cu2 -177.25(17) . . . . ? C24 C23 N4 Cu2 0.8(3) . . . . ? N3 Cu2 N4 C22 177.2(5) . . . . ? Cl2 Cu2 N4 C22 -11.6(4) . . . . ? N3 Cu2 N4 C23 -2.7(3) . . . . ? Cl2 Cu2 N4 C23 168.4(3) . . . . ? O5 C25 N5 C36 -178.5(5) . . . . ? C26 C25 N5 C36 0.0(7) . . . . ? O5 C25 N5 Cu3 -0.4(8) . . . . ? C26 C25 N5 Cu3 178.1(3) . . . . ? C28 C36 N5 C25 0.6(7) . . . . ? C35 C36 N5 C25 -177.3(4) . . . . ? C28 C36 N5 Cu3 -177.8(4) . . . . ? C35 C36 N5 Cu3 4.3(5) . . . . ? O6 Cu3 N5 C25 -4.4(4) . . . . ? N6 Cu3 N5 C25 178.4(4) . . . . ? O6 Cu3 N5 C36 173.8(3) . . . . ? N6 Cu3 N5 C36 -3.4(3) . . . . ? C33 C34 N6 C35 6.7(7) . . . . ? C33 C34 N6 Cu3 -176.6(4) . . . . ? C31 C35 N6 C34 -6.8(7) . . . . ? C36 C35 N6 C34 177.1(4) . . . . ? C31 C35 N6 Cu3 176.0(4) . . . . ? C36 C35 N6 Cu3 -0.1(5) . . . . ? N5 Cu3 N6 C34 -174.9(5) . . . . ? Cl3 Cu3 N6 C34 5.3(5) . . . . ? N5 Cu3 N6 C35 1.9(3) . . . . ? Cl3 Cu3 N6 C35 -177.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1X O2 0.85 1.65 2.487(6) 167 . O2 H2X O5 0.85 1.87 2.652(6) 152 1_645 O3 H3X O4 0.85 1.66 2.503(5) 173 . O4 H4X O1 0.85 1.92 2.715(5) 154 1_565 O5 H5X O6 0.85 1.73 2.570(5) 168 . O6 H6X O3 0.85 1.99 2.780(5) 155 1_455 _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.673 _refine_diff_density_min -0.908 _refine_diff_density_rms 0.105 _database_code_depnum_ccdc_archive 'CCDC 791983' ####################################################################### # # 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_91126bm #TrackingRef 'SUB-CCDC91126bm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H10 Cu N6 O6' _chemical_formula_weight 433.83 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' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.7171(19) _cell_length_b 25.760(6) _cell_length_c 8.772(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.111(3) _cell_angle_gamma 90.00 _cell_volume 1626.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2633 _cell_measurement_theta_min 2.6115 _cell_measurement_theta_max 23.2405 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.771 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 1.395 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6639 _exptl_absorpt_correction_T_max 0.8731 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 Smart APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9445 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 26.99 _reflns_number_total 3519 _reflns_number_gt 2678 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 2001)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0927P)^2^+1.0546P] 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 3519 _refine_ls_number_parameters 253 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1652 _refine_ls_wR_factor_gt 0.1569 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.062 _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 C1 C 0.3295(7) 0.78118(15) 0.9551(6) 0.0534(11) Uani 1 1 d . . . H1 H 0.4079 0.8024 1.0367 0.064 Uiso 1 1 calc R . . C2 C 0.4311(6) 0.69195(14) 1.0668(5) 0.0401(8) Uani 1 1 d . . . C3 C 0.5793(6) 0.70182(17) 1.2131(5) 0.0509(10) Uani 1 1 d . . . H3 H 0.6295 0.7349 1.2383 0.061 Uiso 1 1 calc R . . C4 C 0.6474(6) 0.66119(19) 1.3173(5) 0.0525(11) Uani 1 1 d . . . H4 H 0.7444 0.6669 1.4160 0.063 Uiso 1 1 calc R . . C5 C 0.5746(6) 0.61110(17) 1.2791(5) 0.0454(9) Uani 1 1 d . . . C6 C 0.4316(5) 0.60500(14) 1.1280(5) 0.0390(8) Uani 1 1 d . . . C7 C 0.6293(6) 0.56552(18) 1.3799(5) 0.0535(11) Uani 1 1 d . . . H7 H 0.7213 0.5680 1.4831 0.064 Uiso 1 1 calc R . . C8 C 0.5488(6) 0.51909(17) 1.3265(5) 0.0519(10) Uani 1 1 d . . . H8 H 0.5875 0.4904 1.3946 0.062 Uiso 1 1 calc R . . C9 C 0.3482(5) 0.55632(14) 1.0695(5) 0.0391(8) Uani 1 1 d . . . C10 C 0.4056(6) 0.51245(15) 1.1686(5) 0.0436(9) Uani 1 1 d . . . C11 C 0.3171(6) 0.46561(16) 1.1023(6) 0.0511(10) Uani 1 1 d . . . H11 H 0.3490 0.4352 1.1630 0.061 Uiso 1 1 calc R . . C12 C 0.1864(6) 0.46473(16) 0.9514(6) 0.0509(10) Uani 1 1 d . . . H12 H 0.1286 0.4336 0.9076 0.061 Uiso 1 1 calc R . . C13 C 0.1372(6) 0.51076(16) 0.8597(5) 0.0465(9) Uani 1 1 d . . . H13 H 0.0472 0.5094 0.7553 0.056 Uiso 1 1 calc R . . C14 C 0.1123(7) 0.75182(17) 0.7325(6) 0.0539(11) Uani 1 1 d . . . H14 H 0.0136 0.7513 0.6328 0.065 Uiso 1 1 calc R . . C15 C 0.1897(7) 0.79677(18) 0.8193(6) 0.0611(13) Uani 1 1 d . . . H15 H 0.1522 0.8308 0.7894 0.073 Uiso 1 1 calc R . . Cu1 Cu 0.16609(7) 0.630534(17) 0.82138(6) 0.0417(2) Uani 1 1 d U . . N1 N 0.3337(5) 0.72887(12) 0.9499(4) 0.0430(8) Uani 1 1 d . . . N2 N 0.1983(5) 0.71034(13) 0.8112(4) 0.0459(8) Uani 1 1 d . . . N3 N 0.3633(4) 0.64514(12) 1.0263(4) 0.0389(7) Uani 1 1 d . . . N4 N 0.2147(4) 0.55591(12) 0.9171(4) 0.0393(7) Uani 1 1 d . . . N5 N -0.1908(5) 0.66627(14) 0.8539(5) 0.0499(9) Uani 1 1 d . . . N6 N 0.1656(6) 0.59670(13) 0.5348(5) 0.0558(10) Uani 1 1 d . . . O1 O 0.3285(5) 0.60623(13) 0.6180(4) 0.0627(8) Uani 1 1 d . . . O2 O 0.0413(4) 0.60981(13) 0.5943(4) 0.0587(8) Uani 1 1 d . . . O3 O 0.1153(7) 0.57647(16) 0.4011(4) 0.0931(14) Uani 1 1 d . . . O4 O -0.2277(8) 0.6738(3) 0.7090(6) 0.129(2) Uani 1 1 d . . . O5 O -0.0550(6) 0.64229(18) 0.9306(7) 0.0956(15) Uani 1 1 d U . . O6 O -0.2944(9) 0.6852(3) 0.9069(9) 0.150(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.073(3) 0.037(2) 0.061(3) -0.0055(19) 0.038(3) -0.006(2) C2 0.040(2) 0.040(2) 0.043(2) -0.0058(16) 0.0183(17) -0.0019(16) C3 0.045(2) 0.051(2) 0.055(3) -0.016(2) 0.015(2) -0.0109(19) C4 0.042(2) 0.063(3) 0.045(2) -0.011(2) 0.0073(19) -0.0059(19) C5 0.041(2) 0.052(2) 0.043(2) -0.0052(18) 0.0145(17) 0.0021(18) C6 0.039(2) 0.039(2) 0.041(2) -0.0028(16) 0.0167(16) 0.0017(16) C7 0.044(2) 0.067(3) 0.043(2) 0.004(2) 0.0076(18) 0.006(2) C8 0.055(3) 0.053(2) 0.048(2) 0.012(2) 0.019(2) 0.012(2) C9 0.039(2) 0.0376(19) 0.044(2) 0.0005(16) 0.0181(17) 0.0037(15) C10 0.044(2) 0.044(2) 0.048(2) 0.0016(17) 0.0215(18) 0.0037(17) C11 0.058(3) 0.039(2) 0.064(3) 0.0062(19) 0.031(2) 0.0055(18) C12 0.053(3) 0.037(2) 0.068(3) -0.0039(19) 0.028(2) -0.0077(18) C13 0.045(2) 0.048(2) 0.047(2) -0.0097(18) 0.0164(18) -0.0062(18) C14 0.059(3) 0.050(2) 0.055(3) 0.011(2) 0.024(2) 0.006(2) C15 0.084(4) 0.039(2) 0.072(3) 0.008(2) 0.042(3) 0.005(2) Cu1 0.0401(3) 0.0387(3) 0.0406(3) -0.00201(19) 0.0076(2) 0.00004(19) N1 0.048(2) 0.0389(16) 0.0456(18) -0.0030(14) 0.0210(16) -0.0029(14) N2 0.045(2) 0.0432(18) 0.047(2) 0.0007(15) 0.0136(16) -0.0009(14) N3 0.0371(18) 0.0375(16) 0.0413(17) -0.0060(13) 0.0132(14) -0.0028(13) N4 0.0374(17) 0.0369(16) 0.0420(18) -0.0039(13) 0.0124(14) 0.0000(13) N5 0.040(2) 0.052(2) 0.060(2) -0.0018(17) 0.0216(18) 0.0040(16) N6 0.076(3) 0.0375(18) 0.046(2) -0.0001(15) 0.012(2) 0.0048(18) O1 0.062(2) 0.060(2) 0.065(2) -0.0017(17) 0.0217(17) 0.0056(16) O2 0.0488(19) 0.0620(19) 0.0471(17) -0.0047(15) -0.0049(14) -0.0005(15) O3 0.141(4) 0.080(3) 0.048(2) -0.0233(19) 0.021(2) -0.007(3) O4 0.110(4) 0.207(7) 0.069(3) -0.030(3) 0.031(3) -0.030(4) O5 0.061(3) 0.101(3) 0.145(4) 0.059(3) 0.061(3) 0.029(2) O6 0.158(5) 0.161(5) 0.189(6) 0.067(5) 0.130(5) 0.092(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C15 1.349(7) . ? C1 N1 1.349(5) . ? C1 H1 0.9300 . ? C2 N3 1.311(5) . ? C2 C3 1.401(6) . ? C2 N1 1.402(5) . ? C3 C4 1.364(6) . ? C3 H3 0.9300 . ? C4 C5 1.399(6) . ? C4 H4 0.9300 . ? C5 C6 1.394(6) . ? C5 C7 1.439(6) . ? C6 N3 1.343(5) . ? C6 C9 1.419(5) . ? C7 C8 1.351(6) . ? C7 H7 0.9300 . ? C8 C10 1.438(6) . ? C8 H8 0.9300 . ? C9 N4 1.362(5) . ? C9 C10 1.397(5) . ? C10 C11 1.405(6) . ? C11 C12 1.345(6) . ? C11 H11 0.9300 . ? C12 C13 1.406(6) . ? C12 H12 0.9300 . ? C13 N4 1.322(5) . ? C13 H13 0.9300 . ? C14 N2 1.315(6) . ? C14 C15 1.396(7) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? Cu1 N3 1.929(3) . ? Cu1 O2 1.949(3) . ? Cu1 N2 2.076(3) . ? Cu1 N4 2.077(3) . ? Cu1 O5 2.257(4) . ? N1 N2 1.372(5) . ? N5 O6 1.166(6) . ? N5 O5 1.194(5) . ? N5 O4 1.214(6) . ? N6 O3 1.212(5) . ? N6 O1 1.230(5) . ? N6 O2 1.291(5) . ? 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 C15 C1 N1 106.8(4) . . ? C15 C1 H1 126.6 . . ? N1 C1 H1 126.6 . . ? N3 C2 C3 122.0(4) . . ? N3 C2 N1 111.7(3) . . ? C3 C2 N1 126.3(4) . . ? C4 C3 C2 117.7(4) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C3 C4 C5 121.5(4) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C6 C5 C4 116.3(4) . . ? C6 C5 C7 116.7(4) . . ? C4 C5 C7 127.0(4) . . ? N3 C6 C5 122.1(4) . . ? N3 C6 C9 114.9(3) . . ? C5 C6 C9 123.0(4) . . ? C8 C7 C5 120.8(4) . . ? C8 C7 H7 119.6 . . ? C5 C7 H7 119.6 . . ? C7 C8 C10 122.5(4) . . ? C7 C8 H8 118.8 . . ? C10 C8 H8 118.8 . . ? N4 C9 C10 124.2(4) . . ? N4 C9 C6 116.5(3) . . ? C10 C9 C6 119.3(4) . . ? C9 C10 C11 116.1(4) . . ? C9 C10 C8 117.7(4) . . ? C11 C10 C8 126.2(4) . . ? C12 C11 C10 120.1(4) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 120.1(4) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? N4 C13 C12 122.2(4) . . ? N4 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? N2 C14 C15 110.6(4) . . ? N2 C14 H14 124.7 . . ? C15 C14 H14 124.7 . . ? C1 C15 C14 106.5(4) . . ? C1 C15 H15 126.8 . . ? C14 C15 H15 126.8 . . ? N3 Cu1 O2 160.00(15) . . ? N3 Cu1 N2 77.31(13) . . ? O2 Cu1 N2 104.48(14) . . ? N3 Cu1 N4 80.59(13) . . ? O2 Cu1 N4 96.35(13) . . ? N2 Cu1 N4 157.91(13) . . ? N3 Cu1 O5 92.39(17) . . ? O2 Cu1 O5 107.45(18) . . ? N2 Cu1 O5 90.33(15) . . ? N4 Cu1 O5 90.38(13) . . ? C1 N1 N2 111.0(4) . . ? C1 N1 C2 131.7(4) . . ? N2 N1 C2 116.7(3) . . ? C14 N2 N1 105.2(4) . . ? C14 N2 Cu1 141.4(3) . . ? N1 N2 Cu1 111.8(2) . . ? C2 N3 C6 120.3(3) . . ? C2 N3 Cu1 122.4(3) . . ? C6 N3 Cu1 117.3(3) . . ? C13 N4 C9 117.3(3) . . ? C13 N4 Cu1 132.0(3) . . ? C9 N4 Cu1 110.6(2) . . ? O6 N5 O5 125.5(5) . . ? O6 N5 O4 114.5(5) . . ? O5 N5 O4 120.0(5) . . ? O3 N6 O1 124.2(5) . . ? O3 N6 O2 118.6(5) . . ? O1 N6 O2 117.2(4) . . ? N6 O2 Cu1 108.6(3) . . ? N5 O5 Cu1 118.3(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C2 C3 C4 -2.8(6) . . . . ? N1 C2 C3 C4 175.2(4) . . . . ? C2 C3 C4 C5 1.1(7) . . . . ? C3 C4 C5 C6 1.1(6) . . . . ? C3 C4 C5 C7 -177.8(4) . . . . ? C4 C5 C6 N3 -1.9(6) . . . . ? C7 C5 C6 N3 177.1(4) . . . . ? C4 C5 C6 C9 177.7(4) . . . . ? C7 C5 C6 C9 -3.3(6) . . . . ? C6 C5 C7 C8 2.1(6) . . . . ? C4 C5 C7 C8 -179.0(4) . . . . ? C5 C7 C8 C10 -0.1(7) . . . . ? N3 C6 C9 N4 1.9(5) . . . . ? C5 C6 C9 N4 -177.7(3) . . . . ? N3 C6 C9 C10 -178.0(3) . . . . ? C5 C6 C9 C10 2.4(6) . . . . ? N4 C9 C10 C11 0.3(6) . . . . ? C6 C9 C10 C11 -179.9(4) . . . . ? N4 C9 C10 C8 179.8(4) . . . . ? C6 C9 C10 C8 -0.3(6) . . . . ? C7 C8 C10 C9 -0.8(6) . . . . ? C7 C8 C10 C11 178.7(4) . . . . ? C9 C10 C11 C12 0.4(6) . . . . ? C8 C10 C11 C12 -179.1(4) . . . . ? C10 C11 C12 C13 -0.3(6) . . . . ? C11 C12 C13 N4 -0.4(7) . . . . ? N1 C1 C15 C14 -0.6(5) . . . . ? N2 C14 C15 C1 0.7(5) . . . . ? C15 C1 N1 N2 0.3(5) . . . . ? C15 C1 N1 C2 -169.9(4) . . . . ? N3 C2 N1 C1 165.0(4) . . . . ? C3 C2 N1 C1 -13.2(7) . . . . ? N3 C2 N1 N2 -4.8(5) . . . . ? C3 C2 N1 N2 177.0(4) . . . . ? C15 C14 N2 N1 -0.5(5) . . . . ? C15 C14 N2 Cu1 162.5(4) . . . . ? C1 N1 N2 C14 0.1(5) . . . . ? C2 N1 N2 C14 171.9(3) . . . . ? C1 N1 N2 Cu1 -168.6(3) . . . . ? C2 N1 N2 Cu1 3.3(4) . . . . ? N3 Cu1 N2 C14 -163.1(5) . . . . ? O2 Cu1 N2 C14 37.4(5) . . . . ? N4 Cu1 N2 C14 -162.5(4) . . . . ? O5 Cu1 N2 C14 -70.7(5) . . . . ? N3 Cu1 N2 N1 -0.8(2) . . . . ? O2 Cu1 N2 N1 -160.3(3) . . . . ? N4 Cu1 N2 N1 -0.2(5) . . . . ? O5 Cu1 N2 N1 91.6(3) . . . . ? C3 C2 N3 C6 2.1(6) . . . . ? N1 C2 N3 C6 -176.1(3) . . . . ? C3 C2 N3 Cu1 -177.4(3) . . . . ? N1 C2 N3 Cu1 4.3(5) . . . . ? C5 C6 N3 C2 0.3(6) . . . . ? C9 C6 N3 C2 -179.3(3) . . . . ? C5 C6 N3 Cu1 179.8(3) . . . . ? C9 C6 N3 Cu1 0.2(4) . . . . ? O2 Cu1 N3 C2 95.4(5) . . . . ? N2 Cu1 N3 C2 -2.1(3) . . . . ? N4 Cu1 N3 C2 178.1(3) . . . . ? O5 Cu1 N3 C2 -91.9(3) . . . . ? O2 Cu1 N3 C6 -84.1(5) . . . . ? N2 Cu1 N3 C6 178.4(3) . . . . ? N4 Cu1 N3 C6 -1.4(3) . . . . ? O5 Cu1 N3 C6 88.6(3) . . . . ? C12 C13 N4 C9 1.1(6) . . . . ? C12 C13 N4 Cu1 -176.4(3) . . . . ? C10 C9 N4 C13 -1.0(6) . . . . ? C6 C9 N4 C13 179.1(4) . . . . ? C10 C9 N4 Cu1 177.0(3) . . . . ? C6 C9 N4 Cu1 -2.9(4) . . . . ? N3 Cu1 N4 C13 179.9(4) . . . . ? O2 Cu1 N4 C13 -20.1(4) . . . . ? N2 Cu1 N4 C13 179.3(4) . . . . ? O5 Cu1 N4 C13 87.5(4) . . . . ? N3 Cu1 N4 C9 2.3(2) . . . . ? O2 Cu1 N4 C9 162.4(3) . . . . ? N2 Cu1 N4 C9 1.8(5) . . . . ? O5 Cu1 N4 C9 -90.0(3) . . . . ? O3 N6 O2 Cu1 170.9(3) . . . . ? O1 N6 O2 Cu1 -9.8(4) . . . . ? N3 Cu1 O2 N6 0.1(6) . . . . ? N2 Cu1 O2 N6 92.8(3) . . . . ? N4 Cu1 O2 N6 -79.8(3) . . . . ? O5 Cu1 O2 N6 -172.2(3) . . . . ? O6 N5 O5 Cu1 -161.8(6) . . . . ? O4 N5 O5 Cu1 16.2(7) . . . . ? N3 Cu1 O5 N5 137.0(4) . . . . ? O2 Cu1 O5 N5 -45.7(5) . . . . ? N2 Cu1 O5 N5 59.6(4) . . . . ? N4 Cu1 O5 N5 -142.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.620 _refine_diff_density_min -0.730 _refine_diff_density_rms 0.092 _database_code_depnum_ccdc_archive 'CCDC 817164' ####################################################################### # # 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_71129cm #TrackingRef 'Sub-CCDC-71129cm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 Cl2 Cu N10 O9' _chemical_formula_weight 803.03 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.0975(19) _cell_length_b 14.246(2) _cell_length_c 20.649(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.795(2) _cell_angle_gamma 90.00 _cell_volume 3226.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3922 _cell_measurement_theta_min 2.4335 _cell_measurement_theta_max 23.5495 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.653 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1636 _exptl_absorpt_coefficient_mu 0.916 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7645 _exptl_absorpt_correction_T_max 0.8525 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 SMART APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18587 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.00 _reflns_number_total 6992 _reflns_number_gt 4826 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 2001)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and local programs' _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^)+(0.1050P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6992 _refine_ls_number_parameters 470 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1758 _refine_ls_wR_factor_gt 0.1619 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 C1 C 0.5854(10) 0.0487(11) 0.1879(5) 0.238(8) Uani 1 1 d . . . H1A H 0.5390 -0.0065 0.1738 0.356 Uiso 1 1 calc R . . H1B H 0.6680 0.0406 0.1802 0.356 Uiso 1 1 calc R . . H1C H 0.5501 0.1021 0.1638 0.356 Uiso 1 1 calc R . . C2 C 1.1677(4) 0.4052(3) 0.19882(19) 0.0490(9) Uani 1 1 d . . . H2 H 1.1369 0.4659 0.1982 0.059 Uiso 1 1 calc R . . C3 C 1.2882(4) 0.2938(3) 0.21731(19) 0.0490(9) Uani 1 1 d . . . H3 H 1.3565 0.2569 0.2309 0.059 Uiso 1 1 calc R . . C4 C 1.1471(3) 0.1719(2) 0.16094(15) 0.0344(7) Uani 1 1 d . . . C5 C 1.2231(3) 0.0932(3) 0.16916(17) 0.0425(8) Uani 1 1 d . . . H5 H 1.3017 0.0975 0.1923 0.051 Uiso 1 1 calc R . . C6 C 1.1799(3) 0.0110(2) 0.14281(17) 0.0419(8) Uani 1 1 d . . . H6 H 1.2295 -0.0419 0.1475 0.050 Uiso 1 1 calc R . . C7 C 0.9900(3) 0.0860(2) 0.10359(15) 0.0325(7) Uani 1 1 d . . . C8 C 1.0599(3) 0.0045(2) 0.10808(16) 0.0375(8) Uani 1 1 d . . . C9 C 1.0064(4) -0.0784(2) 0.07712(19) 0.0462(9) Uani 1 1 d . . . H9 H 1.0514 -0.1336 0.0794 0.055 Uiso 1 1 calc R . . C10 C 0.8910(4) -0.0776(2) 0.04452(19) 0.0466(9) Uani 1 1 d . . . H10 H 0.8583 -0.1326 0.0249 0.056 Uiso 1 1 calc R . . C11 C 0.8175(3) 0.0059(2) 0.03931(18) 0.0404(8) Uani 1 1 d . . . C12 C 0.8691(3) 0.0880(2) 0.06972(16) 0.0347(7) Uani 1 1 d . . . C13 C 0.6979(4) 0.0132(3) 0.0049(2) 0.0539(10) Uani 1 1 d . . . H13 H 0.6595 -0.0389 -0.0161 0.065 Uiso 1 1 calc R . . C14 C 0.6395(4) 0.0969(3) 0.0026(2) 0.0560(10) Uani 1 1 d . . . H14 H 0.5606 0.1023 -0.0199 0.067 Uiso 1 1 calc R . . C15 C 0.6976(3) 0.1749(3) 0.03418(19) 0.0463(9) Uani 1 1 d . . . H15 H 0.6556 0.2316 0.0320 0.056 Uiso 1 1 calc R . . C16 C 1.0199(4) 0.3539(3) -0.0296(2) 0.0521(10) Uani 1 1 d . . . H16 H 1.0884 0.3175 -0.0327 0.062 Uiso 1 1 calc R . . C17 C 0.8793(4) 0.4520(3) -0.0543(2) 0.0530(10) Uani 1 1 d . . . H17 H 0.8271 0.4973 -0.0755 0.064 Uiso 1 1 calc R . . C18 C 0.7842(3) 0.4282(2) 0.04719(18) 0.0407(8) Uani 1 1 d . . . C19 C 0.6895(4) 0.4938(2) 0.0337(2) 0.0519(10) Uani 1 1 d . . . H19 H 0.6779 0.5274 -0.0054 0.062 Uiso 1 1 calc R . . C20 C 0.6149(4) 0.5069(3) 0.0797(2) 0.0545(11) Uani 1 1 d . . . H20 H 0.5515 0.5501 0.0719 0.065 Uiso 1 1 calc R . . C21 C 0.6323(3) 0.4564(2) 0.1385(2) 0.0460(9) Uani 1 1 d . . . C22 C 0.7281(3) 0.3910(2) 0.14735(17) 0.0366(8) Uani 1 1 d . . . C23 C 0.7534(3) 0.3364(2) 0.20526(18) 0.0403(8) Uani 1 1 d . . . C24 C 0.6834(4) 0.3501(3) 0.2552(2) 0.0512(10) Uani 1 1 d . . . C25 C 0.5595(4) 0.4660(3) 0.1896(2) 0.0593(11) Uani 1 1 d . . . H25 H 0.4944 0.5079 0.1845 0.071 Uiso 1 1 calc R . . C26 C 0.5837(4) 0.4156(3) 0.2447(2) 0.0660(13) Uani 1 1 d . . . H26 H 0.5347 0.4232 0.2771 0.079 Uiso 1 1 calc R . . C27 C 0.7183(5) 0.2978(4) 0.3130(2) 0.0677(13) Uani 1 1 d . . . H27 H 0.6749 0.3036 0.3480 0.081 Uiso 1 1 calc R . . C28 C 0.8157(5) 0.2390(4) 0.3174(2) 0.0715(14) Uani 1 1 d . . . H28 H 0.8411 0.2064 0.3561 0.086 Uiso 1 1 calc R . . C29 C 0.8760(4) 0.2278(3) 0.2651(2) 0.0538(10) Uani 1 1 d . . . H29 H 0.9399 0.1850 0.2685 0.065 Uiso 1 1 calc R . . C30 C 0.5843(6) 0.0629(6) 0.2555(6) 0.157(4) Uani 1 1 d . . . H30A H 0.6589 0.0955 0.2731 0.188 Uiso 1 1 calc R . . H30B H 0.5873 0.0018 0.2763 0.188 Uiso 1 1 calc R . . Cl1 Cl 0.32106(10) 0.71710(7) 0.13462(5) 0.0556(3) Uani 1 1 d . . . Cl2 Cl 0.36680(10) 0.27465(7) 0.04506(6) 0.0554(3) Uani 1 1 d . . . Cu1 Cu 0.92509(4) 0.27692(3) 0.11802(2) 0.03499(16) Uani 1 1 d . . . N1 N 1.1034(3) 0.3348(2) 0.17163(14) 0.0413(7) Uani 1 1 d . . . N2 N 1.1829(3) 0.2617(2) 0.18424(14) 0.0363(6) Uani 1 1 d . . . N3 N 1.2818(3) 0.3840(2) 0.22780(17) 0.0536(8) Uani 1 1 d . . . N4 N 1.0345(2) 0.16869(18) 0.12956(13) 0.0327(6) Uani 1 1 d . . . N5 N 0.8090(3) 0.17192(19) 0.06693(14) 0.0375(6) Uani 1 1 d . . . N6 N 0.8476(3) 0.27524(19) 0.20966(14) 0.0405(7) Uani 1 1 d . . . N7 N 0.8046(3) 0.37841(18) 0.10198(14) 0.0364(6) Uani 1 1 d . . . N8 N 0.8675(3) 0.4115(2) 0.00401(14) 0.0413(7) Uani 1 1 d . . . N9 N 0.9591(3) 0.3477(2) 0.02001(15) 0.0459(8) Uani 1 1 d . . . N10 N 0.9747(3) 0.4179(3) -0.07620(17) 0.0612(9) Uani 1 1 d . . . O1 O 0.4656(4) 0.3269(3) 0.0363(3) 0.1177(17) Uani 1 1 d . . . O2 O 0.2835(5) 0.3345(4) 0.0687(2) 0.153(2) Uani 1 1 d . . . O3 O 0.3195(7) 0.2478(5) -0.0207(2) 0.173(3) Uani 1 1 d . . . O4 O 0.3960(6) 0.1979(4) 0.0834(3) 0.157(2) Uani 1 1 d . . . O5 O 0.3842(4) 0.7982(3) 0.1607(2) 0.1010(13) Uani 1 1 d . . . O6 O 0.3797(4) 0.6724(3) 0.0867(2) 0.1076(14) Uani 1 1 d . . . O7 O 0.3156(4) 0.6526(3) 0.18530(18) 0.1025(14) Uani 1 1 d . . . O8 O 0.2052(3) 0.7454(3) 0.1048(2) 0.1056(15) Uani 1 1 d . . . O9 O 0.4810(3) 0.1156(3) 0.2760(2) 0.0941(12) Uani 1 1 d . . . H9A H 0.4888 0.1170 0.3161 0.141 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 C1 0.198(11) 0.411(19) 0.114(7) 0.077(10) 0.057(7) 0.199(13) C2 0.054(2) 0.045(2) 0.049(2) -0.0040(18) 0.014(2) 0.0042(19) C3 0.034(2) 0.063(3) 0.047(2) -0.0011(19) -0.0009(17) 0.0007(17) C4 0.0348(18) 0.0399(19) 0.0287(16) 0.0024(14) 0.0055(14) 0.0035(15) C5 0.0361(19) 0.049(2) 0.0398(19) 0.0083(16) -0.0008(16) 0.0101(16) C6 0.049(2) 0.0375(19) 0.0402(19) 0.0106(15) 0.0089(17) 0.0156(16) C7 0.0394(18) 0.0295(16) 0.0294(16) 0.0001(13) 0.0076(14) 0.0015(14) C8 0.045(2) 0.0339(18) 0.0354(18) 0.0058(14) 0.0130(16) 0.0048(15) C9 0.061(3) 0.0291(18) 0.051(2) 0.0052(16) 0.017(2) 0.0102(17) C10 0.064(3) 0.0288(18) 0.049(2) -0.0037(16) 0.015(2) -0.0050(17) C11 0.045(2) 0.0333(18) 0.045(2) -0.0036(15) 0.0104(17) -0.0083(15) C12 0.0379(18) 0.0339(17) 0.0326(17) 0.0013(14) 0.0068(15) 0.0016(14) C13 0.050(2) 0.051(2) 0.060(3) -0.0081(19) 0.006(2) -0.0152(19) C14 0.041(2) 0.058(3) 0.066(3) -0.004(2) -0.003(2) -0.0054(19) C15 0.036(2) 0.048(2) 0.053(2) -0.0026(18) 0.0022(17) 0.0047(17) C16 0.051(2) 0.054(2) 0.052(2) 0.0015(19) 0.009(2) -0.0019(19) C17 0.057(3) 0.048(2) 0.051(2) 0.0149(19) 0.001(2) -0.0030(19) C18 0.043(2) 0.0305(17) 0.046(2) 0.0002(15) -0.0008(17) -0.0022(15) C19 0.057(2) 0.034(2) 0.059(2) 0.0035(18) -0.010(2) 0.0055(17) C20 0.043(2) 0.038(2) 0.077(3) -0.011(2) -0.011(2) 0.0118(17) C21 0.037(2) 0.0347(19) 0.063(2) -0.0126(18) -0.0032(18) 0.0015(15) C22 0.0323(17) 0.0324(17) 0.0446(19) -0.0070(15) 0.0039(15) -0.0005(14) C23 0.0342(18) 0.0398(19) 0.046(2) -0.0081(16) 0.0041(16) 0.0006(15) C24 0.045(2) 0.056(2) 0.054(2) -0.0126(19) 0.0141(19) -0.0025(18) C25 0.039(2) 0.060(3) 0.080(3) -0.016(2) 0.011(2) 0.0120(19) C26 0.055(3) 0.078(3) 0.070(3) -0.023(3) 0.025(2) 0.001(2) C27 0.074(3) 0.084(3) 0.051(3) -0.002(2) 0.028(2) -0.004(3) C28 0.088(4) 0.084(3) 0.044(2) 0.016(2) 0.016(3) 0.010(3) C29 0.053(2) 0.058(3) 0.050(2) 0.0023(19) 0.005(2) 0.0065(19) C30 0.061(4) 0.115(6) 0.282(13) -0.009(7) -0.015(6) 0.020(4) Cl1 0.0556(6) 0.0584(6) 0.0497(6) -0.0066(5) -0.0015(5) 0.0097(5) Cl2 0.0532(6) 0.0483(6) 0.0671(7) 0.0075(5) 0.0164(5) -0.0001(5) Cu1 0.0349(3) 0.0316(2) 0.0379(3) -0.00072(17) 0.00398(18) 0.00436(17) N1 0.0390(17) 0.0402(17) 0.0442(17) 0.0024(14) 0.0046(14) 0.0087(14) N2 0.0347(16) 0.0384(15) 0.0351(15) 0.0005(12) 0.0028(13) 0.0049(12) N3 0.052(2) 0.050(2) 0.058(2) -0.0131(16) 0.0093(17) -0.0046(16) N4 0.0329(15) 0.0318(14) 0.0336(14) 0.0010(12) 0.0054(12) 0.0034(12) N5 0.0359(16) 0.0332(15) 0.0432(16) -0.0012(13) 0.0053(13) 0.0029(12) N6 0.0407(17) 0.0424(17) 0.0382(16) 0.0004(13) 0.0054(14) 0.0020(13) N7 0.0393(16) 0.0266(13) 0.0424(16) -0.0017(12) 0.0031(13) 0.0017(12) N8 0.0473(18) 0.0337(15) 0.0407(16) 0.0059(13) -0.0001(14) -0.0017(13) N9 0.0467(18) 0.0403(17) 0.0476(18) 0.0042(14) -0.0022(15) 0.0037(14) N10 0.067(2) 0.064(2) 0.052(2) 0.0083(18) 0.0058(19) -0.0033(19) O1 0.068(3) 0.082(3) 0.204(5) 0.027(3) 0.023(3) -0.005(2) O2 0.153(4) 0.211(5) 0.115(3) 0.092(4) 0.086(3) 0.124(4) O3 0.247(8) 0.183(5) 0.085(3) -0.045(4) 0.009(4) -0.072(5) O4 0.219(6) 0.104(3) 0.168(5) 0.077(3) 0.101(5) 0.062(4) O5 0.090(3) 0.079(2) 0.124(3) -0.020(2) -0.014(3) -0.011(2) O6 0.132(4) 0.109(3) 0.092(3) -0.007(2) 0.051(3) 0.037(3) O7 0.163(4) 0.081(3) 0.067(2) 0.015(2) 0.031(3) 0.006(3) O8 0.063(2) 0.084(2) 0.156(4) -0.018(3) -0.031(3) 0.0216(19) O9 0.078(3) 0.108(3) 0.092(3) 0.025(2) -0.002(2) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C30 1.411(12) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N1 1.306(5) . ? C2 N3 1.349(5) . ? C2 H2 0.9300 . ? C3 N3 1.307(5) . ? C3 N2 1.341(5) . ? C3 H3 0.9300 . ? C4 N4 1.318(4) . ? C4 C5 1.397(5) . ? C4 N2 1.402(4) . ? C5 C6 1.348(5) . ? C5 H5 0.9300 . ? C6 C8 1.416(5) . ? C6 H6 0.9300 . ? C7 N4 1.355(4) . ? C7 C8 1.392(4) . ? C7 C12 1.415(5) . ? C8 C9 1.428(5) . ? C9 C10 1.353(5) . ? C9 H9 0.9300 . ? C10 C11 1.437(5) . ? C10 H10 0.9300 . ? C11 C12 1.406(5) . ? C11 C13 1.410(5) . ? C12 N5 1.366(4) . ? C13 C14 1.353(6) . ? C13 H13 0.9300 . ? C14 C15 1.396(5) . ? C14 H14 0.9300 . ? C15 N5 1.317(4) . ? C15 H15 0.9300 . ? C16 N9 1.313(5) . ? C16 N10 1.364(5) . ? C16 H16 0.9300 . ? C17 N10 1.308(5) . ? C17 N8 1.359(5) . ? C17 H17 0.9300 . ? C18 N7 1.325(4) . ? C18 N8 1.400(5) . ? C18 C19 1.402(5) . ? C19 C20 1.365(6) . ? C19 H19 0.9300 . ? C20 C21 1.399(6) . ? C20 H20 0.9300 . ? C21 C22 1.405(5) . ? C21 C25 1.430(6) . ? C22 N7 1.369(4) . ? C22 C23 1.418(5) . ? C23 N6 1.353(4) . ? C23 C24 1.397(5) . ? C24 C27 1.410(6) . ? C24 C26 1.438(6) . ? C25 C26 1.336(7) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C28 1.360(7) . ? C27 H27 0.9300 . ? C28 C29 1.365(6) . ? C28 H28 0.9300 . ? C29 N6 1.325(5) . ? C29 H29 0.9300 . ? C30 O9 1.485(8) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? Cl1 O8 1.398(4) . ? Cl1 O7 1.401(4) . ? Cl1 O5 1.415(4) . ? Cl1 O6 1.417(4) . ? Cl2 O4 1.360(4) . ? Cl2 O1 1.360(4) . ? Cl2 O2 1.399(4) . ? Cl2 O3 1.432(5) . ? Cu1 N4 1.954(3) . ? Cu1 N7 1.963(3) . ? Cu1 N5 2.143(3) . ? Cu1 N6 2.195(3) . ? Cu1 N1 2.270(3) . ? Cu1 N9 2.343(3) . ? N1 N2 1.365(4) . ? N8 N9 1.366(4) . ? O9 H9A 0.8200 . ? 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 C30 C1 H1A 109.5 . . ? C30 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C30 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N3 115.6(3) . . ? N1 C2 H2 122.2 . . ? N3 C2 H2 122.2 . . ? N3 C3 N2 110.8(4) . . ? N3 C3 H3 124.6 . . ? N2 C3 H3 124.6 . . ? N4 C4 C5 122.8(3) . . ? N4 C4 N2 113.4(3) . . ? C5 C4 N2 123.8(3) . . ? C6 C5 C4 118.5(3) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? C5 C6 C8 120.7(3) . . ? C5 C6 H6 119.7 . . ? C8 C6 H6 119.7 . . ? N4 C7 C8 122.2(3) . . ? N4 C7 C12 116.0(3) . . ? C8 C7 C12 121.7(3) . . ? C7 C8 C6 116.8(3) . . ? C7 C8 C9 118.0(3) . . ? C6 C8 C9 125.2(3) . . ? C10 C9 C8 120.9(3) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 121.8(3) . . ? C9 C10 H10 119.1 . . ? C11 C10 H10 119.1 . . ? C12 C11 C13 116.8(3) . . ? C12 C11 C10 117.8(3) . . ? C13 C11 C10 125.3(3) . . ? N5 C12 C11 123.1(3) . . ? N5 C12 C7 117.2(3) . . ? C11 C12 C7 119.7(3) . . ? C14 C13 C11 119.4(4) . . ? C14 C13 H13 120.3 . . ? C11 C13 H13 120.3 . . ? C13 C14 C15 120.1(4) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? N5 C15 C14 123.0(4) . . ? N5 C15 H15 118.5 . . ? C14 C15 H15 118.5 . . ? N9 C16 N10 114.7(4) . . ? N9 C16 H16 122.6 . . ? N10 C16 H16 122.6 . . ? N10 C17 N8 110.0(4) . . ? N10 C17 H17 125.0 . . ? N8 C17 H17 125.0 . . ? N7 C18 N8 114.2(3) . . ? N7 C18 C19 123.5(4) . . ? N8 C18 C19 122.3(3) . . ? C20 C19 C18 117.9(4) . . ? C20 C19 H19 121.0 . . ? C18 C19 H19 121.0 . . ? C19 C20 C21 121.1(3) . . ? C19 C20 H20 119.5 . . ? C21 C20 H20 119.5 . . ? C20 C21 C22 117.0(4) . . ? C20 C21 C25 125.0(4) . . ? C22 C21 C25 118.0(4) . . ? N7 C22 C21 122.3(3) . . ? N7 C22 C23 116.2(3) . . ? C21 C22 C23 121.4(3) . . ? N6 C23 C24 123.5(4) . . ? N6 C23 C22 117.5(3) . . ? C24 C23 C22 119.0(3) . . ? C23 C24 C27 116.1(4) . . ? C23 C24 C26 118.7(4) . . ? C27 C24 C26 125.2(4) . . ? C26 C25 C21 120.9(4) . . ? C26 C25 H25 119.5 . . ? C21 C25 H25 119.5 . . ? C25 C26 C24 121.8(4) . . ? C25 C26 H26 119.1 . . ? C24 C26 H26 119.1 . . ? C28 C27 C24 119.7(4) . . ? C28 C27 H27 120.2 . . ? C24 C27 H27 120.2 . . ? C27 C28 C29 120.1(4) . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? N6 C29 C28 122.9(4) . . ? N6 C29 H29 118.6 . . ? C28 C29 H29 118.6 . . ? C1 C30 O9 118.6(7) . . ? C1 C30 H30A 107.7 . . ? O9 C30 H30A 107.7 . . ? C1 C30 H30B 107.7 . . ? O9 C30 H30B 107.7 . . ? H30A C30 H30B 107.1 . . ? O8 Cl1 O7 112.1(3) . . ? O8 Cl1 O5 107.5(3) . . ? O7 Cl1 O5 109.1(3) . . ? O8 Cl1 O6 108.2(3) . . ? O7 Cl1 O6 107.7(2) . . ? O5 Cl1 O6 112.4(3) . . ? O4 Cl2 O1 113.1(3) . . ? O4 Cl2 O2 113.5(3) . . ? O1 Cl2 O2 107.6(3) . . ? O4 Cl2 O3 111.0(4) . . ? O1 Cl2 O3 101.9(4) . . ? O2 Cl2 O3 109.1(4) . . ? N4 Cu1 N7 174.98(11) . . ? N4 Cu1 N5 79.90(11) . . ? N7 Cu1 N5 95.08(11) . . ? N4 Cu1 N6 101.79(11) . . ? N7 Cu1 N6 78.86(11) . . ? N5 Cu1 N6 97.55(11) . . ? N4 Cu1 N1 75.43(11) . . ? N7 Cu1 N1 109.57(11) . . ? N5 Cu1 N1 155.12(10) . . ? N6 Cu1 N1 90.63(11) . . ? N4 Cu1 N9 105.40(11) . . ? N7 Cu1 N9 74.51(11) . . ? N5 Cu1 N9 92.24(11) . . ? N6 Cu1 N9 152.31(10) . . ? N1 Cu1 N9 91.22(11) . . ? C2 N1 N2 102.1(3) . . ? C2 N1 Cu1 150.1(3) . . ? N2 N1 Cu1 107.8(2) . . ? C3 N2 N1 108.9(3) . . ? C3 N2 C4 131.7(3) . . ? N1 N2 C4 119.4(3) . . ? C3 N3 C2 102.6(3) . . ? C4 N4 C7 119.1(3) . . ? C4 N4 Cu1 123.9(2) . . ? C7 N4 Cu1 117.1(2) . . ? C15 N5 C12 117.6(3) . . ? C15 N5 Cu1 132.6(2) . . ? C12 N5 Cu1 109.7(2) . . ? C29 N6 C23 117.8(3) . . ? C29 N6 Cu1 132.6(3) . . ? C23 N6 Cu1 109.6(2) . . ? C18 N7 C22 118.1(3) . . ? C18 N7 Cu1 124.2(2) . . ? C22 N7 Cu1 117.3(2) . . ? C17 N8 N9 109.1(3) . . ? C17 N8 C18 130.9(3) . . ? N9 N8 C18 119.9(3) . . ? C16 N9 N8 102.6(3) . . ? C16 N9 Cu1 150.8(3) . . ? N8 N9 Cu1 106.4(2) . . ? C17 N10 C16 103.5(3) . . ? C30 O9 H9A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C4 C5 C6 1.3(5) . . . . ? N2 C4 C5 C6 -178.0(3) . . . . ? C4 C5 C6 C8 -0.5(5) . . . . ? N4 C7 C8 C6 1.6(5) . . . . ? C12 C7 C8 C6 179.6(3) . . . . ? N4 C7 C8 C9 -177.8(3) . . . . ? C12 C7 C8 C9 0.2(5) . . . . ? C5 C6 C8 C7 -0.8(5) . . . . ? C5 C6 C8 C9 178.5(3) . . . . ? C7 C8 C9 C10 -0.1(5) . . . . ? C6 C8 C9 C10 -179.5(3) . . . . ? C8 C9 C10 C11 0.2(6) . . . . ? C9 C10 C11 C12 -0.4(5) . . . . ? C9 C10 C11 C13 178.3(4) . . . . ? C13 C11 C12 N5 -0.1(5) . . . . ? C10 C11 C12 N5 178.6(3) . . . . ? C13 C11 C12 C7 -178.3(3) . . . . ? C10 C11 C12 C7 0.4(5) . . . . ? N4 C7 C12 N5 -0.5(4) . . . . ? C8 C7 C12 N5 -178.6(3) . . . . ? N4 C7 C12 C11 177.8(3) . . . . ? C8 C7 C12 C11 -0.3(5) . . . . ? C12 C11 C13 C14 0.0(6) . . . . ? C10 C11 C13 C14 -178.6(4) . . . . ? C11 C13 C14 C15 0.0(6) . . . . ? C13 C14 C15 N5 0.0(7) . . . . ? N7 C18 C19 C20 0.1(6) . . . . ? N8 C18 C19 C20 -178.3(3) . . . . ? C18 C19 C20 C21 0.0(6) . . . . ? C19 C20 C21 C22 -1.1(5) . . . . ? C19 C20 C21 C25 179.5(4) . . . . ? C20 C21 C22 N7 2.2(5) . . . . ? C25 C21 C22 N7 -178.4(3) . . . . ? C20 C21 C22 C23 179.9(3) . . . . ? C25 C21 C22 C23 -0.6(5) . . . . ? N7 C22 C23 N6 -2.0(5) . . . . ? C21 C22 C23 N6 -179.9(3) . . . . ? N7 C22 C23 C24 176.1(3) . . . . ? C21 C22 C23 C24 -1.8(5) . . . . ? N6 C23 C24 C27 1.8(6) . . . . ? C22 C23 C24 C27 -176.2(4) . . . . ? N6 C23 C24 C26 -178.7(4) . . . . ? C22 C23 C24 C26 3.3(6) . . . . ? C20 C21 C25 C26 -179.1(4) . . . . ? C22 C21 C25 C26 1.4(6) . . . . ? C21 C25 C26 C24 0.2(7) . . . . ? C23 C24 C26 C25 -2.6(7) . . . . ? C27 C24 C26 C25 176.8(5) . . . . ? C23 C24 C27 C28 0.4(7) . . . . ? C26 C24 C27 C28 -179.0(5) . . . . ? C24 C27 C28 C29 -2.7(8) . . . . ? C27 C28 C29 N6 3.0(8) . . . . ? N3 C2 N1 N2 0.1(4) . . . . ? N3 C2 N1 Cu1 176.4(3) . . . . ? N4 Cu1 N1 C2 -179.1(5) . . . . ? N7 Cu1 N1 C2 1.3(5) . . . . ? N5 Cu1 N1 C2 173.2(4) . . . . ? N6 Cu1 N1 C2 -77.1(5) . . . . ? N9 Cu1 N1 C2 75.3(5) . . . . ? N4 Cu1 N1 N2 -2.90(19) . . . . ? N7 Cu1 N1 N2 177.52(19) . . . . ? N5 Cu1 N1 N2 -10.5(4) . . . . ? N6 Cu1 N1 N2 99.1(2) . . . . ? N9 Cu1 N1 N2 -108.5(2) . . . . ? N3 C3 N2 N1 0.8(4) . . . . ? N3 C3 N2 C4 178.6(3) . . . . ? C2 N1 N2 C3 -0.5(4) . . . . ? Cu1 N1 N2 C3 -178.6(2) . . . . ? C2 N1 N2 C4 -178.6(3) . . . . ? Cu1 N1 N2 C4 3.3(3) . . . . ? N4 C4 N2 C3 -179.3(3) . . . . ? C5 C4 N2 C3 0.0(6) . . . . ? N4 C4 N2 N1 -1.7(4) . . . . ? C5 C4 N2 N1 177.6(3) . . . . ? N2 C3 N3 C2 -0.6(4) . . . . ? N1 C2 N3 C3 0.3(5) . . . . ? C5 C4 N4 C7 -0.5(5) . . . . ? N2 C4 N4 C7 178.8(3) . . . . ? C5 C4 N4 Cu1 179.3(2) . . . . ? N2 C4 N4 Cu1 -1.5(4) . . . . ? C8 C7 N4 C4 -1.0(5) . . . . ? C12 C7 N4 C4 -179.1(3) . . . . ? C8 C7 N4 Cu1 179.2(2) . . . . ? C12 C7 N4 Cu1 1.2(4) . . . . ? N7 Cu1 N4 C4 178(29) . . . . ? N5 Cu1 N4 C4 179.2(3) . . . . ? N6 Cu1 N4 C4 -85.1(3) . . . . ? N1 Cu1 N4 C4 2.5(2) . . . . ? N9 Cu1 N4 C4 89.7(3) . . . . ? N7 Cu1 N4 C7 -2.3(14) . . . . ? N5 Cu1 N4 C7 -1.0(2) . . . . ? N6 Cu1 N4 C7 94.7(2) . . . . ? N1 Cu1 N4 C7 -177.8(2) . . . . ? N9 Cu1 N4 C7 -90.6(2) . . . . ? C14 C15 N5 C12 -0.1(5) . . . . ? C14 C15 N5 Cu1 178.2(3) . . . . ? C11 C12 N5 C15 0.2(5) . . . . ? C7 C12 N5 C15 178.4(3) . . . . ? C11 C12 N5 Cu1 -178.5(3) . . . . ? C7 C12 N5 Cu1 -0.3(3) . . . . ? N4 Cu1 N5 C15 -177.7(3) . . . . ? N7 Cu1 N5 C15 2.1(3) . . . . ? N6 Cu1 N5 C15 81.5(3) . . . . ? N1 Cu1 N5 C15 -170.3(3) . . . . ? N9 Cu1 N5 C15 -72.5(3) . . . . ? N4 Cu1 N5 C12 0.7(2) . . . . ? N7 Cu1 N5 C12 -179.5(2) . . . . ? N6 Cu1 N5 C12 -100.0(2) . . . . ? N1 Cu1 N5 C12 8.2(4) . . . . ? N9 Cu1 N5 C12 105.9(2) . . . . ? C28 C29 N6 C23 -0.8(6) . . . . ? C28 C29 N6 Cu1 178.8(3) . . . . ? C24 C23 N6 C29 -1.7(5) . . . . ? C22 C23 N6 C29 176.3(3) . . . . ? C24 C23 N6 Cu1 178.6(3) . . . . ? C22 C23 N6 Cu1 -3.3(4) . . . . ? N4 Cu1 N6 C29 10.8(4) . . . . ? N7 Cu1 N6 C29 -174.2(4) . . . . ? N5 Cu1 N6 C29 92.0(4) . . . . ? N1 Cu1 N6 C29 -64.4(4) . . . . ? N9 Cu1 N6 C29 -158.2(3) . . . . ? N4 Cu1 N6 C23 -169.5(2) . . . . ? N7 Cu1 N6 C23 5.4(2) . . . . ? N5 Cu1 N6 C23 -88.3(2) . . . . ? N1 Cu1 N6 C23 115.2(2) . . . . ? N9 Cu1 N6 C23 21.4(4) . . . . ? N8 C18 N7 C22 179.4(3) . . . . ? C19 C18 N7 C22 0.9(5) . . . . ? N8 C18 N7 Cu1 -8.3(4) . . . . ? C19 C18 N7 Cu1 173.2(3) . . . . ? C21 C22 N7 C18 -2.1(5) . . . . ? C23 C22 N7 C18 -179.9(3) . . . . ? C21 C22 N7 Cu1 -174.9(3) . . . . ? C23 C22 N7 Cu1 7.2(4) . . . . ? N4 Cu1 N7 C18 -81.2(13) . . . . ? N5 Cu1 N7 C18 -82.5(3) . . . . ? N6 Cu1 N7 C18 -179.2(3) . . . . ? N1 Cu1 N7 C18 94.2(3) . . . . ? N9 Cu1 N7 C18 8.5(3) . . . . ? N4 Cu1 N7 C22 91.2(13) . . . . ? N5 Cu1 N7 C22 89.9(2) . . . . ? N6 Cu1 N7 C22 -6.8(2) . . . . ? N1 Cu1 N7 C22 -93.5(2) . . . . ? N9 Cu1 N7 C22 -179.2(3) . . . . ? N10 C17 N8 N9 -0.6(4) . . . . ? N10 C17 N8 C18 176.5(3) . . . . ? N7 C18 N8 C17 -176.3(4) . . . . ? C19 C18 N8 C17 2.2(6) . . . . ? N7 C18 N8 N9 0.6(4) . . . . ? C19 C18 N8 N9 179.1(3) . . . . ? N10 C16 N9 N8 0.6(4) . . . . ? N10 C16 N9 Cu1 175.2(4) . . . . ? C17 N8 N9 C16 0.0(4) . . . . ? C18 N8 N9 C16 -177.5(3) . . . . ? C17 N8 N9 Cu1 -177.3(2) . . . . ? C18 N8 N9 Cu1 5.3(3) . . . . ? N4 Cu1 N9 C16 -6.4(6) . . . . ? N7 Cu1 N9 C16 178.8(6) . . . . ? N5 Cu1 N9 C16 -86.6(5) . . . . ? N6 Cu1 N9 C16 162.5(5) . . . . ? N1 Cu1 N9 C16 68.8(5) . . . . ? N4 Cu1 N9 N8 168.1(2) . . . . ? N7 Cu1 N9 N8 -6.7(2) . . . . ? N5 Cu1 N9 N8 87.9(2) . . . . ? N6 Cu1 N9 N8 -23.0(4) . . . . ? N1 Cu1 N9 N8 -116.7(2) . . . . ? N8 C17 N10 C16 0.9(5) . . . . ? N9 C16 N10 C17 -1.0(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O9 H9A N10 0.82 2.31 3.101(5) 163.0 4_566 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.975 _refine_diff_density_min -0.517 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 897431' ####################################################################### # # 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_110908am #TrackingRef 'Sub-CCDC-110908am-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 Cl2 Cu N4' _chemical_formula_weight 394.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.113(2) _cell_length_b 8.852(2) _cell_length_c 10.802(3) _cell_angle_alpha 93.092(4) _cell_angle_beta 98.507(4) _cell_angle_gamma 93.259(4) _cell_volume 764.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1618 _cell_measurement_theta_min 2.309 _cell_measurement_theta_max 28.8215 _exptl_crystal_description green _exptl_crystal_colour prism _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.715 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 398 _exptl_absorpt_coefficient_mu 1.781 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7399 _exptl_absorpt_correction_T_max 0.8420 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3964 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.49 _reflns_number_total 2766 _reflns_number_gt 2255 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 2001)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0517P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2766 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.003 _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 C1 C -0.1872(5) 0.4207(4) 0.6946(4) 0.0514(10) Uani 1 1 d . . . H1A H -0.2815 0.4345 0.7373 0.077 Uiso 1 1 calc R . . H1B H -0.2010 0.4730 0.6186 0.077 Uiso 1 1 calc R . . H1C H -0.0870 0.4606 0.7477 0.077 Uiso 1 1 calc R . . C2 C -0.1751(4) 0.2567(4) 0.6640(3) 0.0357(8) Uani 1 1 d . . . C3 C -0.2999(4) 0.1519(4) 0.5993(3) 0.0389(9) Uani 1 1 d . . . H3 H -0.4090 0.1719 0.5677 0.047 Uiso 1 1 calc R . . C4 C -0.2312(4) 0.0176(4) 0.5918(3) 0.0355(8) Uani 1 1 d . . . H4 H -0.2831 -0.0729 0.5535 0.043 Uiso 1 1 calc R . . C5 C 0.0568(4) -0.0591(4) 0.6723(3) 0.0296(7) Uani 1 1 d . . . C6 C 0.0437(4) -0.2143(4) 0.6368(3) 0.0362(8) Uani 1 1 d . . . H6 H -0.0562 -0.2617 0.5957 0.043 Uiso 1 1 calc R . . C7 C 0.1822(5) -0.2937(4) 0.6643(3) 0.0383(8) Uani 1 1 d . . . H7 H 0.1765 -0.3970 0.6418 0.046 Uiso 1 1 calc R . . C8 C 0.3340(4) -0.2222(4) 0.7262(3) 0.0327(8) Uani 1 1 d . . . C9 C 0.3322(4) -0.0684(4) 0.7580(3) 0.0296(7) Uani 1 1 d . . . C10 C 0.4743(4) 0.0161(4) 0.8256(3) 0.0293(7) Uani 1 1 d . . . C11 C 0.6217(4) -0.0558(4) 0.8585(3) 0.0348(8) Uani 1 1 d . . . C12 C 0.6231(5) -0.2129(4) 0.8231(3) 0.0435(9) Uani 1 1 d . . . H12 H 0.7208 -0.2619 0.8442 0.052 Uiso 1 1 calc R . . C13 C 0.4865(5) -0.2935(4) 0.7596(3) 0.0417(9) Uani 1 1 d . . . H13 H 0.4921 -0.3959 0.7377 0.050 Uiso 1 1 calc R . . C14 C 0.7564(5) 0.0355(4) 0.9250(3) 0.0430(9) Uani 1 1 d . . . H14 H 0.8582 -0.0056 0.9495 0.052 Uiso 1 1 calc R . . C15 C 0.7373(5) 0.1851(5) 0.9535(3) 0.0441(9) Uani 1 1 d . . . H15 H 0.8270 0.2462 0.9964 0.053 Uiso 1 1 calc R . . C16 C 0.5839(4) 0.2469(4) 0.9185(3) 0.0395(9) Uani 1 1 d . . . H16 H 0.5727 0.3484 0.9406 0.047 Uiso 1 1 calc R . . Cl1 Cl 0.31167(10) 0.33214(9) 0.59329(8) 0.0363(2) Uani 1 1 d . . . Cl2 Cl 0.19823(14) 0.42154(11) 0.91252(9) 0.0553(3) Uani 1 1 d . . . Cu1 Cu 0.21678(5) 0.22969(4) 0.77693(4) 0.03213(16) Uani 1 1 d . . . N1 N 0.4539(3) 0.1654(3) 0.8548(2) 0.0321(7) Uani 1 1 d . . . N2 N 0.1969(3) 0.0112(3) 0.7307(2) 0.0278(6) Uani 1 1 d . . . N3 N -0.0711(3) 0.0398(3) 0.6512(2) 0.0310(6) Uani 1 1 d . . . N4 N -0.0355(3) 0.1882(3) 0.6967(3) 0.0320(6) 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 C1 0.044(2) 0.037(2) 0.076(3) 0.009(2) 0.013(2) 0.0141(18) C2 0.037(2) 0.0332(19) 0.041(2) 0.0098(16) 0.0138(16) 0.0108(16) C3 0.0294(19) 0.043(2) 0.045(2) 0.0084(17) 0.0034(16) 0.0074(17) C4 0.0280(18) 0.039(2) 0.039(2) 0.0033(16) 0.0015(15) 0.0025(16) C5 0.0337(18) 0.0274(18) 0.0295(18) 0.0043(14) 0.0073(14) 0.0071(15) C6 0.038(2) 0.0270(18) 0.041(2) 0.0027(15) -0.0016(16) 0.0008(16) C7 0.047(2) 0.0244(18) 0.042(2) -0.0020(15) 0.0031(17) 0.0049(16) C8 0.0375(19) 0.0290(18) 0.0318(18) 0.0041(15) 0.0023(15) 0.0088(16) C9 0.0344(18) 0.0237(17) 0.0307(18) 0.0033(14) 0.0027(14) 0.0062(14) C10 0.0328(18) 0.0290(18) 0.0268(17) 0.0072(14) 0.0037(14) 0.0051(15) C11 0.0333(19) 0.042(2) 0.0289(18) 0.0079(15) 0.0012(15) 0.0079(16) C12 0.039(2) 0.047(2) 0.045(2) 0.0065(18) 0.0019(17) 0.0202(19) C13 0.051(2) 0.0307(19) 0.044(2) 0.0038(16) 0.0034(18) 0.0158(18) C14 0.034(2) 0.055(3) 0.039(2) 0.0086(18) -0.0028(16) 0.0090(18) C15 0.037(2) 0.053(2) 0.037(2) 0.0002(18) -0.0048(16) -0.0068(19) C16 0.043(2) 0.036(2) 0.038(2) -0.0022(16) 0.0022(17) 0.0002(17) Cl1 0.0387(5) 0.0298(4) 0.0399(5) 0.0034(4) 0.0030(4) 0.0055(4) Cl2 0.0665(7) 0.0440(6) 0.0511(6) -0.0169(5) -0.0038(5) 0.0197(5) Cu1 0.0341(3) 0.0238(2) 0.0375(3) -0.00055(17) 0.00135(18) 0.00658(17) N1 0.0352(16) 0.0286(16) 0.0310(16) 0.0019(12) 0.0010(12) 0.0005(13) N2 0.0276(14) 0.0246(14) 0.0310(15) 0.0024(11) 0.0010(12) 0.0073(12) N3 0.0270(15) 0.0253(15) 0.0405(16) 0.0025(12) 0.0024(12) 0.0067(12) N4 0.0326(15) 0.0240(14) 0.0403(16) 0.0024(12) 0.0060(12) 0.0068(12) _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 C1 C2 1.483(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N4 1.326(4) . ? C2 C3 1.410(5) . ? C3 C4 1.345(5) . ? C3 H3 0.9300 . ? C4 N3 1.359(4) . ? C4 H4 0.9300 . ? C5 N2 1.320(4) . ? C5 N3 1.397(4) . ? C5 C6 1.400(4) . ? C6 C7 1.363(5) . ? C6 H6 0.9300 . ? C7 C8 1.409(5) . ? C7 H7 0.9300 . ? C8 C9 1.387(4) . ? C8 C13 1.428(5) . ? C9 N2 1.343(4) . ? C9 C10 1.420(4) . ? C10 N1 1.367(4) . ? C10 C11 1.395(5) . ? C11 C14 1.403(5) . ? C11 C12 1.423(5) . ? C12 C13 1.356(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.366(5) . ? C14 H14 0.9300 . ? C15 C16 1.397(5) . ? C15 H15 0.9300 . ? C16 N1 1.323(4) . ? C16 H16 0.9300 . ? Cl1 Cu1 2.4322(10) . ? Cl2 Cu1 2.2086(11) . ? Cu1 N2 1.962(3) . ? Cu1 N4 2.105(3) . ? Cu1 N1 2.105(3) . ? N3 N4 1.376(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N4 C2 C3 110.1(3) . . ? N4 C2 C1 121.9(3) . . ? C3 C2 C1 128.0(3) . . ? C4 C3 C2 106.9(3) . . ? C4 C3 H3 126.6 . . ? C2 C3 H3 126.6 . . ? C3 C4 N3 106.7(3) . . ? C3 C4 H4 126.7 . . ? N3 C4 H4 126.7 . . ? N2 C5 N3 111.8(3) . . ? N2 C5 C6 122.5(3) . . ? N3 C5 C6 125.7(3) . . ? C7 C6 C5 117.8(3) . . ? C7 C6 H6 121.1 . . ? C5 C6 H6 121.1 . . ? C6 C7 C8 121.2(3) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C9 C8 C7 116.0(3) . . ? C9 C8 C13 117.9(3) . . ? C7 C8 C13 126.1(3) . . ? N2 C9 C8 123.3(3) . . ? N2 C9 C10 114.8(3) . . ? C8 C9 C10 121.9(3) . . ? N1 C10 C11 124.6(3) . . ? N1 C10 C9 115.9(3) . . ? C11 C10 C9 119.4(3) . . ? C10 C11 C14 116.0(3) . . ? C10 C11 C12 118.2(3) . . ? C14 C11 C12 125.9(3) . . ? C13 C12 C11 122.2(3) . . ? C13 C12 H12 118.9 . . ? C11 C12 H12 118.9 . . ? C12 C13 C8 120.5(3) . . ? C12 C13 H13 119.8 . . ? C8 C13 H13 119.8 . . ? C15 C14 C11 119.7(3) . . ? C15 C14 H14 120.2 . . ? C11 C14 H14 120.2 . . ? C14 C15 C16 120.4(3) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? N1 C16 C15 122.0(3) . . ? N1 C16 H16 119.0 . . ? C15 C16 H16 119.0 . . ? N2 Cu1 N4 76.39(10) . . ? N2 Cu1 N1 78.66(10) . . ? N4 Cu1 N1 154.30(11) . . ? N2 Cu1 Cl2 150.43(8) . . ? N4 Cu1 Cl2 100.65(8) . . ? N1 Cu1 Cl2 97.97(8) . . ? N2 Cu1 Cl1 101.69(8) . . ? N4 Cu1 Cl1 96.35(8) . . ? N1 Cu1 Cl1 94.61(8) . . ? Cl2 Cu1 Cl1 107.87(4) . . ? C16 N1 C10 117.3(3) . . ? C16 N1 Cu1 130.6(2) . . ? C10 N1 Cu1 111.9(2) . . ? C5 N2 C9 119.1(3) . . ? C5 N2 Cu1 122.4(2) . . ? C9 N2 Cu1 118.4(2) . . ? C4 N3 N4 111.2(3) . . ? C4 N3 C5 131.6(3) . . ? N4 N3 C5 117.2(3) . . ? C2 N4 N3 105.1(3) . . ? C2 N4 Cu1 142.6(2) . . ? N3 N4 Cu1 111.98(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C2 C3 C4 -0.9(4) . . . . ? C1 C2 C3 C4 178.9(4) . . . . ? C2 C3 C4 N3 0.7(4) . . . . ? N2 C5 C6 C7 0.0(5) . . . . ? N3 C5 C6 C7 179.6(3) . . . . ? C5 C6 C7 C8 -0.2(5) . . . . ? C6 C7 C8 C9 0.8(5) . . . . ? C6 C7 C8 C13 -180.0(3) . . . . ? C7 C8 C9 N2 -1.2(5) . . . . ? C13 C8 C9 N2 179.4(3) . . . . ? C7 C8 C9 C10 177.1(3) . . . . ? C13 C8 C9 C10 -2.2(5) . . . . ? N2 C9 C10 N1 0.7(4) . . . . ? C8 C9 C10 N1 -177.8(3) . . . . ? N2 C9 C10 C11 -179.8(3) . . . . ? C8 C9 C10 C11 1.7(5) . . . . ? N1 C10 C11 C14 -0.7(5) . . . . ? C9 C10 C11 C14 179.9(3) . . . . ? N1 C10 C11 C12 179.0(3) . . . . ? C9 C10 C11 C12 -0.4(5) . . . . ? C10 C11 C12 C13 -0.3(5) . . . . ? C14 C11 C12 C13 179.4(3) . . . . ? C11 C12 C13 C8 -0.3(5) . . . . ? C9 C8 C13 C12 1.5(5) . . . . ? C7 C8 C13 C12 -177.7(3) . . . . ? C10 C11 C14 C15 0.1(5) . . . . ? C12 C11 C14 C15 -179.6(4) . . . . ? C11 C14 C15 C16 1.0(6) . . . . ? C14 C15 C16 N1 -1.6(5) . . . . ? C15 C16 N1 C10 1.0(5) . . . . ? C15 C16 N1 Cu1 -174.3(2) . . . . ? C11 C10 N1 C16 0.2(5) . . . . ? C9 C10 N1 C16 179.6(3) . . . . ? C11 C10 N1 Cu1 176.3(2) . . . . ? C9 C10 N1 Cu1 -4.3(3) . . . . ? N2 Cu1 N1 C16 -179.9(3) . . . . ? N4 Cu1 N1 C16 -165.8(3) . . . . ? Cl2 Cu1 N1 C16 -29.7(3) . . . . ? Cl1 Cu1 N1 C16 79.1(3) . . . . ? N2 Cu1 N1 C10 4.7(2) . . . . ? N4 Cu1 N1 C10 18.7(4) . . . . ? Cl2 Cu1 N1 C10 154.9(2) . . . . ? Cl1 Cu1 N1 C10 -96.3(2) . . . . ? N3 C5 N2 C9 179.9(3) . . . . ? C6 C5 N2 C9 -0.4(5) . . . . ? N3 C5 N2 Cu1 -1.2(4) . . . . ? C6 C5 N2 Cu1 178.5(2) . . . . ? C8 C9 N2 C5 1.1(5) . . . . ? C10 C9 N2 C5 -177.4(3) . . . . ? C8 C9 N2 Cu1 -177.9(2) . . . . ? C10 C9 N2 Cu1 3.7(4) . . . . ? N4 Cu1 N2 C5 2.7(2) . . . . ? N1 Cu1 N2 C5 176.5(3) . . . . ? Cl2 Cu1 N2 C5 90.3(3) . . . . ? Cl1 Cu1 N2 C5 -91.1(2) . . . . ? N4 Cu1 N2 C9 -178.4(2) . . . . ? N1 Cu1 N2 C9 -4.6(2) . . . . ? Cl2 Cu1 N2 C9 -90.8(3) . . . . ? Cl1 Cu1 N2 C9 87.8(2) . . . . ? C3 C4 N3 N4 -0.3(4) . . . . ? C3 C4 N3 C5 179.8(3) . . . . ? N2 C5 N3 C4 177.6(3) . . . . ? C6 C5 N3 C4 -2.1(6) . . . . ? N2 C5 N3 N4 -2.3(4) . . . . ? C6 C5 N3 N4 178.1(3) . . . . ? C3 C2 N4 N3 0.7(4) . . . . ? C1 C2 N4 N3 -179.1(3) . . . . ? C3 C2 N4 Cu1 173.6(3) . . . . ? C1 C2 N4 Cu1 -6.1(6) . . . . ? C4 N3 N4 C2 -0.2(3) . . . . ? C5 N3 N4 C2 179.7(3) . . . . ? C4 N3 N4 Cu1 -175.6(2) . . . . ? C5 N3 N4 Cu1 4.3(3) . . . . ? N2 Cu1 N4 C2 -176.2(4) . . . . ? N1 Cu1 N4 C2 169.6(3) . . . . ? Cl2 Cu1 N4 C2 33.9(4) . . . . ? Cl1 Cu1 N4 C2 -75.7(4) . . . . ? N2 Cu1 N4 N3 -3.6(2) . . . . ? N1 Cu1 N4 N3 -17.7(4) . . . . ? Cl2 Cu1 N4 N3 -153.44(19) . . . . ? Cl1 Cu1 N4 N3 97.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.417 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 897429' ####################################################################### # # 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_110922am #TrackingRef 'Sub-CCDC-110922am.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 Br2 Cu N4' _chemical_formula_weight 483.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 8.0958(16) _cell_length_b 9.0668(18) _cell_length_c 10.991(2) _cell_angle_alpha 92.376(3) _cell_angle_beta 96.640(3) _cell_angle_gamma 94.368(2) _cell_volume 798.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1852 _cell_measurement_theta_min 2.2555 _cell_measurement_theta_max 27.607 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.013 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 470 _exptl_absorpt_coefficient_mu 6.378 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2137 _exptl_absorpt_correction_T_max 0.4688 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 Smart APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4338 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3043 _reflns_number_gt 2491 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 2001)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0495P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3043 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0964 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.009 _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 Br1 Br 0.18713(6) 0.41408(5) 0.42146(5) 0.05081(17) Uani 1 1 d . . . Br2 Br 0.32097(5) 0.34079(4) 0.08748(4) 0.03425(14) Uani 1 1 d . . . C1 C -0.1799(6) 0.4082(5) 0.1834(5) 0.0481(12) Uani 1 1 d . . . H1A H -0.1127 0.4403 0.2589 0.072 Uiso 1 1 calc R . . H1B H -0.2938 0.4272 0.1893 0.072 Uiso 1 1 calc R . . H1C H -0.1401 0.4614 0.1174 0.072 Uiso 1 1 calc R . . C2 C -0.1691(5) 0.2473(4) 0.1596(4) 0.0321(9) Uani 1 1 d . . . C3 C -0.2932(5) 0.1450(5) 0.0971(4) 0.0371(10) Uani 1 1 d . . . H3 H -0.4000 0.1645 0.0645 0.045 Uiso 1 1 calc R . . C4 C -0.2256(5) 0.0115(5) 0.0939(4) 0.0340(9) Uani 1 1 d . . . H4 H -0.2770 -0.0776 0.0580 0.041 Uiso 1 1 calc R . . C5 C 0.0580(5) -0.0600(4) 0.1761(4) 0.0286(9) Uani 1 1 d . . . C6 C 0.0453(5) -0.2125(4) 0.1440(4) 0.0352(10) Uani 1 1 d . . . H6 H -0.0540 -0.2602 0.1056 0.042 Uiso 1 1 calc R . . C7 C 0.1824(5) -0.2879(4) 0.1709(4) 0.0380(10) Uani 1 1 d . . . H7 H 0.1770 -0.3887 0.1498 0.046 Uiso 1 1 calc R . . C8 C 0.3345(5) -0.2157(4) 0.2306(4) 0.0335(9) Uani 1 1 d . . . C9 C 0.3311(5) -0.0663(4) 0.2608(4) 0.0285(9) Uani 1 1 d . . . C10 C 0.4716(5) 0.0198(4) 0.3251(4) 0.0292(9) Uani 1 1 d . . . C11 C 0.6181(5) -0.0489(5) 0.3581(4) 0.0320(9) Uani 1 1 d . . . C12 C 0.6206(6) -0.2016(5) 0.3246(4) 0.0423(11) Uani 1 1 d . . . H12 H 0.7181 -0.2477 0.3447 0.051 Uiso 1 1 calc R . . C13 C 0.4844(6) -0.2836(5) 0.2636(4) 0.0403(11) Uani 1 1 d . . . H13 H 0.4902 -0.3837 0.2439 0.048 Uiso 1 1 calc R . . C14 C 0.7504(5) 0.0424(5) 0.4223(4) 0.0421(11) Uani 1 1 d . . . H14 H 0.8513 0.0035 0.4468 0.051 Uiso 1 1 calc R . . C15 C 0.7312(5) 0.1874(5) 0.4486(4) 0.0423(11) Uani 1 1 d . . . H15 H 0.8193 0.2477 0.4907 0.051 Uiso 1 1 calc R . . C16 C 0.5785(5) 0.2465(5) 0.4123(4) 0.0368(10) Uani 1 1 d . . . H16 H 0.5668 0.3457 0.4318 0.044 Uiso 1 1 calc R . . Cu1 Cu 0.21585(6) 0.22321(5) 0.27515(5) 0.03050(16) Uani 1 1 d . . . N1 N -0.0330(4) 0.1804(3) 0.1950(3) 0.0310(8) Uani 1 1 d . . . N2 N -0.0683(4) 0.0348(3) 0.1536(3) 0.0319(8) Uani 1 1 d . . . N3 N 0.1968(4) 0.0095(3) 0.2321(3) 0.0282(7) Uani 1 1 d . . . N4 N 0.4507(4) 0.1640(4) 0.3508(3) 0.0302(7) 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 Br1 0.0587(3) 0.0457(3) 0.0460(3) -0.0163(2) -0.0051(2) 0.0187(2) Br2 0.0368(2) 0.0295(2) 0.0359(3) 0.00185(17) 0.00050(19) 0.00445(17) C1 0.046(3) 0.034(2) 0.065(3) 0.004(2) 0.004(3) 0.012(2) C2 0.030(2) 0.035(2) 0.033(2) 0.0075(18) 0.0034(18) 0.0094(17) C3 0.028(2) 0.046(3) 0.037(3) 0.008(2) 0.0000(19) 0.0060(18) C4 0.027(2) 0.035(2) 0.039(2) -0.0009(19) 0.0015(19) 0.0001(17) C5 0.030(2) 0.028(2) 0.028(2) 0.0007(17) 0.0010(17) 0.0029(16) C6 0.034(2) 0.026(2) 0.043(3) -0.0022(18) 0.000(2) -0.0016(17) C7 0.049(3) 0.023(2) 0.040(3) -0.0004(18) -0.002(2) 0.0032(18) C8 0.040(2) 0.026(2) 0.035(2) 0.0026(18) 0.003(2) 0.0084(17) C9 0.031(2) 0.028(2) 0.027(2) 0.0031(17) 0.0038(17) 0.0047(16) C10 0.031(2) 0.031(2) 0.026(2) 0.0040(17) 0.0044(17) 0.0044(16) C11 0.032(2) 0.041(2) 0.023(2) 0.0047(18) 0.0015(18) 0.0086(18) C12 0.037(2) 0.047(3) 0.046(3) 0.009(2) 0.002(2) 0.022(2) C13 0.049(3) 0.032(2) 0.041(3) 0.001(2) 0.000(2) 0.0140(19) C14 0.034(2) 0.059(3) 0.034(3) 0.003(2) -0.001(2) 0.009(2) C15 0.035(2) 0.052(3) 0.035(3) 0.000(2) -0.004(2) -0.008(2) C16 0.038(2) 0.037(2) 0.033(2) -0.0028(19) 0.002(2) -0.0016(19) Cu1 0.0310(3) 0.0235(3) 0.0359(3) -0.0021(2) -0.0011(2) 0.00496(19) N1 0.0309(18) 0.0228(16) 0.040(2) 0.0005(15) 0.0040(16) 0.0049(13) N2 0.0284(17) 0.0269(18) 0.039(2) -0.0013(16) -0.0018(16) 0.0028(14) N3 0.0288(17) 0.0241(16) 0.0315(19) 0.0022(14) 0.0000(15) 0.0057(13) N4 0.0308(17) 0.0292(17) 0.0291(18) 0.0003(14) -0.0002(15) 0.0000(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Cu1 2.3563(7) . ? Br2 Cu1 2.5624(7) . ? C1 C2 1.483(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N1 1.325(5) . ? C2 C3 1.409(6) . ? C3 C4 1.367(6) . ? C3 H3 0.9300 . ? C4 N2 1.361(5) . ? C4 H4 0.9300 . ? C5 N3 1.318(5) . ? C5 N2 1.392(5) . ? C5 C6 1.406(5) . ? C6 C7 1.358(6) . ? C6 H6 0.9300 . ? C7 C8 1.425(6) . ? C7 H7 0.9300 . ? C8 C9 1.385(5) . ? C8 C13 1.419(6) . ? C9 N3 1.344(5) . ? C9 C10 1.426(5) . ? C10 N4 1.354(5) . ? C10 C11 1.399(6) . ? C11 C14 1.404(6) . ? C11 C12 1.421(6) . ? C12 C13 1.371(6) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.359(6) . ? C14 H14 0.9300 . ? C15 C16 1.407(6) . ? C15 H15 0.9300 . ? C16 N4 1.329(5) . ? C16 H16 0.9300 . ? Cu1 N3 1.966(3) . ? Cu1 N4 2.103(3) . ? Cu1 N1 2.104(3) . ? N1 N2 1.377(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 110.4(4) . . ? N1 C2 C1 122.4(4) . . ? C3 C2 C1 127.3(4) . . ? C4 C3 C2 106.5(4) . . ? C4 C3 H3 126.7 . . ? C2 C3 H3 126.7 . . ? N2 C4 C3 106.3(4) . . ? N2 C4 H4 126.8 . . ? C3 C4 H4 126.8 . . ? N3 C5 N2 112.3(3) . . ? N3 C5 C6 122.0(4) . . ? N2 C5 C6 125.7(3) . . ? C7 C6 C5 117.9(4) . . ? C7 C6 H6 121.0 . . ? C5 C6 H6 121.0 . . ? C6 C7 C8 121.3(4) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C9 C8 C13 118.3(4) . . ? C9 C8 C7 115.7(4) . . ? C13 C8 C7 126.0(4) . . ? N3 C9 C8 123.2(4) . . ? N3 C9 C10 114.6(3) . . ? C8 C9 C10 122.3(4) . . ? N4 C10 C11 124.9(4) . . ? N4 C10 C9 116.3(3) . . ? C11 C10 C9 118.9(4) . . ? C10 C11 C14 115.7(4) . . ? C10 C11 C12 118.2(4) . . ? C14 C11 C12 126.1(4) . . ? C13 C12 C11 122.4(4) . . ? C13 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? C12 C13 C8 120.0(4) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? C15 C14 C11 120.1(4) . . ? C15 C14 H14 120.0 . . ? C11 C14 H14 120.0 . . ? C14 C15 C16 120.2(4) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? N4 C16 C15 121.6(4) . . ? N4 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? N3 Cu1 N4 78.82(13) . . ? N3 Cu1 N1 76.39(12) . . ? N4 Cu1 N1 154.70(12) . . ? N3 Cu1 Br1 147.65(10) . . ? N4 Cu1 Br1 97.51(9) . . ? N1 Cu1 Br1 100.70(9) . . ? N3 Cu1 Br2 104.00(10) . . ? N4 Cu1 Br2 95.33(9) . . ? N1 Cu1 Br2 95.43(10) . . ? Br1 Cu1 Br2 108.34(3) . . ? C2 N1 N2 105.5(3) . . ? C2 N1 Cu1 142.1(3) . . ? N2 N1 Cu1 112.1(2) . . ? C4 N2 N1 111.3(3) . . ? C4 N2 C5 131.6(3) . . ? N1 N2 C5 117.1(3) . . ? C5 N3 C9 119.8(3) . . ? C5 N3 Cu1 122.1(3) . . ? C9 N3 Cu1 118.1(3) . . ? C16 N4 C10 117.6(4) . . ? C16 N4 Cu1 130.2(3) . . ? C10 N4 Cu1 112.0(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 C4 -1.0(5) . . . . ? C1 C2 C3 C4 177.9(4) . . . . ? C2 C3 C4 N2 0.6(5) . . . . ? N3 C5 C6 C7 -1.0(6) . . . . ? N2 C5 C6 C7 178.7(4) . . . . ? C5 C6 C7 C8 0.5(7) . . . . ? C6 C7 C8 C9 1.2(6) . . . . ? C6 C7 C8 C13 179.5(4) . . . . ? C13 C8 C9 N3 178.8(4) . . . . ? C7 C8 C9 N3 -2.6(6) . . . . ? C13 C8 C9 C10 -1.0(6) . . . . ? C7 C8 C9 C10 177.6(4) . . . . ? N3 C9 C10 N4 1.3(5) . . . . ? C8 C9 C10 N4 -178.8(4) . . . . ? N3 C9 C10 C11 -179.4(4) . . . . ? C8 C9 C10 C11 0.4(6) . . . . ? N4 C10 C11 C14 -0.2(6) . . . . ? C9 C10 C11 C14 -179.3(4) . . . . ? N4 C10 C11 C12 179.9(4) . . . . ? C9 C10 C11 C12 0.7(6) . . . . ? C10 C11 C12 C13 -1.2(7) . . . . ? C14 C11 C12 C13 178.8(4) . . . . ? C11 C12 C13 C8 0.7(7) . . . . ? C9 C8 C13 C12 0.4(7) . . . . ? C7 C8 C13 C12 -177.9(4) . . . . ? C10 C11 C14 C15 0.1(6) . . . . ? C12 C11 C14 C15 -180.0(4) . . . . ? C11 C14 C15 C16 0.4(7) . . . . ? C14 C15 C16 N4 -0.7(7) . . . . ? C3 C2 N1 N2 0.9(5) . . . . ? C1 C2 N1 N2 -178.1(4) . . . . ? C3 C2 N1 Cu1 173.2(3) . . . . ? C1 C2 N1 Cu1 -5.8(7) . . . . ? N3 Cu1 N1 C2 -174.6(5) . . . . ? N4 Cu1 N1 C2 173.7(4) . . . . ? Br1 Cu1 N1 C2 38.4(5) . . . . ? Br2 Cu1 N1 C2 -71.5(5) . . . . ? N3 Cu1 N1 N2 -2.6(3) . . . . ? N4 Cu1 N1 N2 -14.3(5) . . . . ? Br1 Cu1 N1 N2 -149.6(2) . . . . ? Br2 Cu1 N1 N2 100.5(2) . . . . ? C3 C4 N2 N1 -0.1(5) . . . . ? C3 C4 N2 C5 -178.5(4) . . . . ? C2 N1 N2 C4 -0.5(4) . . . . ? Cu1 N1 N2 C4 -175.4(3) . . . . ? C2 N1 N2 C5 178.2(3) . . . . ? Cu1 N1 N2 C5 3.3(4) . . . . ? N3 C5 N2 C4 176.4(4) . . . . ? C6 C5 N2 C4 -3.3(7) . . . . ? N3 C5 N2 N1 -1.9(5) . . . . ? C6 C5 N2 N1 178.3(4) . . . . ? N2 C5 N3 C9 179.9(3) . . . . ? C6 C5 N3 C9 -0.4(6) . . . . ? N2 C5 N3 Cu1 -0.6(5) . . . . ? C6 C5 N3 Cu1 179.2(3) . . . . ? C8 C9 N3 C5 2.3(6) . . . . ? C10 C9 N3 C5 -177.9(4) . . . . ? C8 C9 N3 Cu1 -177.3(3) . . . . ? C10 C9 N3 Cu1 2.5(5) . . . . ? N4 Cu1 N3 C5 176.7(3) . . . . ? N1 Cu1 N3 C5 1.8(3) . . . . ? Br1 Cu1 N3 C5 90.4(3) . . . . ? Br2 Cu1 N3 C5 -90.5(3) . . . . ? N4 Cu1 N3 C9 -3.7(3) . . . . ? N1 Cu1 N3 C9 -178.6(3) . . . . ? Br1 Cu1 N3 C9 -90.1(3) . . . . ? Br2 Cu1 N3 C9 89.1(3) . . . . ? C15 C16 N4 C10 0.6(6) . . . . ? C15 C16 N4 Cu1 -175.5(3) . . . . ? C11 C10 N4 C16 -0.2(6) . . . . ? C9 C10 N4 C16 179.0(4) . . . . ? C11 C10 N4 Cu1 176.7(3) . . . . ? C9 C10 N4 Cu1 -4.2(4) . . . . ? N3 Cu1 N4 C16 -179.5(4) . . . . ? N1 Cu1 N4 C16 -167.9(3) . . . . ? Br1 Cu1 N4 C16 -32.1(4) . . . . ? Br2 Cu1 N4 C16 77.3(4) . . . . ? N3 Cu1 N4 C10 4.2(3) . . . . ? N1 Cu1 N4 C10 15.8(5) . . . . ? Br1 Cu1 N4 C10 151.6(3) . . . . ? Br2 Cu1 N4 C10 -99.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.727 _refine_diff_density_min -0.577 _refine_diff_density_rms 0.115 _database_code_depnum_ccdc_archive 'CCDC 897430' ####################################################################### # # 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_101111am #TrackingRef 'Sub-CCDC-101111am.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 Cu N7 O7' _chemical_formula_weight 480.89 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' 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 9.188(12) _cell_length_b 9.476(12) _cell_length_c 12.122(15) _cell_angle_alpha 69.245(17) _cell_angle_beta 85.180(18) _cell_angle_gamma 73.112(15) _cell_volume 944(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1718 _cell_measurement_theta_min 2.317 _cell_measurement_theta_max 23.1915 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.692 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 490 _exptl_absorpt_coefficient_mu 1.216 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7931 _exptl_absorpt_correction_T_max 0.8293 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 Smart APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5162 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3619 _reflns_number_gt 2909 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 2001)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0876P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3619 _refine_ls_number_parameters 281 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1442 _refine_ls_wR_factor_gt 0.1370 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.002 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 C1 C 0.6271(5) 0.3032(5) 0.7857(4) 0.0525(10) Uani 1 1 d . . . H1 H 0.7053 0.2522 0.7475 0.063 Uiso 1 1 calc R . . C2 C 0.5432(6) 0.2161(5) 0.8702(4) 0.0598(12) Uani 1 1 d . . . H2 H 0.5677 0.1079 0.8881 0.072 Uiso 1 1 calc R . . C3 C 0.4264(5) 0.2873(5) 0.9265(4) 0.0581(11) Uani 1 1 d . . . H3 H 0.3697 0.2284 0.9807 0.070 Uiso 1 1 calc R . . C4 C 0.3918(4) 0.4498(5) 0.9026(3) 0.0479(10) Uani 1 1 d . . . C5 C 0.4828(4) 0.5276(4) 0.8187(3) 0.0404(8) Uani 1 1 d . . . C6 C 0.2769(5) 0.5404(6) 0.9559(4) 0.0591(12) Uani 1 1 d . . . H6 H 0.2157 0.4902 1.0119 0.071 Uiso 1 1 calc R . . C7 C 0.2533(5) 0.6960(6) 0.9287(4) 0.0562(11) Uani 1 1 d . . . H7 H 0.1769 0.7505 0.9660 0.067 Uiso 1 1 calc R . . C8 C 0.3445(4) 0.7788(5) 0.8428(3) 0.0452(9) Uani 1 1 d . . . C9 C 0.4581(4) 0.6923(4) 0.7916(3) 0.0399(8) Uani 1 1 d . . . C10 C 0.3344(5) 0.9402(5) 0.8071(4) 0.0530(10) Uani 1 1 d . . . H10 H 0.2609 1.0041 0.8396 0.064 Uiso 1 1 calc R . . C11 C 0.4310(4) 1.0043(5) 0.7253(4) 0.0483(10) Uani 1 1 d . . . H11 H 0.4229 1.1111 0.7014 0.058 Uiso 1 1 calc R . . C12 C 0.5418(4) 0.9061(4) 0.6788(3) 0.0396(8) Uani 1 1 d . . . C13 C 0.6780(4) 1.0870(4) 0.5356(3) 0.0443(9) Uani 1 1 d . . . H13 H 0.6297 1.1825 0.5454 0.053 Uiso 1 1 calc R . . C14 C 0.7928(4) 1.0618(5) 0.4608(4) 0.0463(9) Uani 1 1 d . . . H14 H 0.8381 1.1358 0.4099 0.056 Uiso 1 1 calc R . . C15 C 0.8300(4) 0.9001(4) 0.4759(3) 0.0407(8) Uani 1 1 d . . . C16 C 1.0159(6) 0.3950(6) 0.8056(5) 0.0794(15) Uani 1 1 d . . . H16A H 0.9760 0.3111 0.8076 0.119 Uiso 1 1 calc R . . H16B H 1.0487 0.3779 0.8836 0.119 Uiso 1 1 calc R . . H16C H 1.1007 0.3978 0.7537 0.119 Uiso 1 1 calc R . . Cu1 Cu 0.70254(5) 0.61817(5) 0.64584(4) 0.03951(19) Uani 1 1 d . . . N1 N 0.5964(4) 0.4586(4) 0.7591(3) 0.0427(7) Uani 1 1 d . . . N2 N 0.5544(3) 0.7547(3) 0.7120(3) 0.0380(7) Uani 1 1 d . . . N3 N 0.6460(3) 0.9492(3) 0.5931(3) 0.0412(7) Uani 1 1 d . . . N4 N 0.7392(3) 0.8310(3) 0.5558(3) 0.0414(7) Uani 1 1 d . . . N5 N 0.9336(4) 0.8231(4) 0.4200(3) 0.0539(9) Uani 1 1 d . . . H5A H 0.9448 0.7249 0.4343 0.065 Uiso 1 1 calc R . . H5B H 0.9901 0.8710 0.3692 0.065 Uiso 1 1 calc R . . N6 N 0.7185(4) 0.5136(4) 0.4655(3) 0.0489(8) Uani 1 1 d . . . N7 N 0.8953(5) 0.8831(5) 0.8082(5) 0.0761(12) Uani 1 1 d . . . H4 H 0.9384 0.6237 0.7585 0.114 Uiso 1 1 d RD . . O1 O 0.9021(3) 0.5388(4) 0.7644(3) 0.0710(9) Uani 1 1 d D . . O2 O 0.9776(5) 0.8078(6) 0.7450(4) 0.0983(13) Uani 1 1 d . . . O3 O 0.8111(6) 0.8253(8) 0.8732(5) 0.142(2) Uani 1 1 d . . . O4 O 0.9128(6) 1.0095(5) 0.7920(5) 0.1233(17) Uani 1 1 d . . . O5 O 0.6000(4) 0.6187(4) 0.4506(3) 0.0680(9) Uani 1 1 d . . . O6 O 0.7577(4) 0.4321(4) 0.4045(3) 0.0817(11) Uani 1 1 d . . . O7 O 0.8076(3) 0.4886(3) 0.5525(3) 0.0531(7) 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 C1 0.060(3) 0.043(2) 0.057(3) -0.015(2) -0.005(2) -0.0194(19) C2 0.081(3) 0.044(2) 0.055(3) -0.003(2) -0.013(2) -0.031(2) C3 0.067(3) 0.060(3) 0.048(2) -0.001(2) -0.003(2) -0.039(2) C4 0.044(2) 0.059(3) 0.037(2) -0.0055(19) -0.0066(17) -0.0225(19) C5 0.0370(19) 0.046(2) 0.0376(19) -0.0098(17) -0.0053(16) -0.0148(16) C6 0.044(2) 0.085(3) 0.046(2) -0.014(2) 0.0057(19) -0.029(2) C7 0.039(2) 0.079(3) 0.047(2) -0.021(2) 0.0048(18) -0.013(2) C8 0.0365(19) 0.060(2) 0.037(2) -0.0164(19) -0.0051(16) -0.0087(17) C9 0.0341(18) 0.048(2) 0.0352(19) -0.0096(17) -0.0040(15) -0.0117(16) C10 0.042(2) 0.062(3) 0.051(2) -0.025(2) 0.0014(19) -0.0017(19) C11 0.050(2) 0.040(2) 0.052(2) -0.0190(19) -0.0071(19) -0.0019(18) C12 0.0364(18) 0.044(2) 0.0378(19) -0.0141(17) -0.0065(15) -0.0079(15) C13 0.046(2) 0.0341(19) 0.051(2) -0.0125(18) -0.0071(18) -0.0098(16) C14 0.049(2) 0.040(2) 0.049(2) -0.0063(18) -0.0059(18) -0.0197(17) C15 0.0374(19) 0.041(2) 0.041(2) -0.0083(17) -0.0074(16) -0.0108(16) C16 0.062(3) 0.079(4) 0.081(4) -0.023(3) -0.006(3) 0.000(3) Cu1 0.0398(3) 0.0330(3) 0.0433(3) -0.0113(2) 0.00146(19) -0.00912(19) N1 0.0482(18) 0.0394(17) 0.0411(17) -0.0102(14) -0.0053(14) -0.0162(14) N2 0.0359(15) 0.0343(15) 0.0415(17) -0.0110(13) -0.0018(13) -0.0081(12) N3 0.0417(16) 0.0326(16) 0.0470(18) -0.0120(14) -0.0009(14) -0.0087(13) N4 0.0421(17) 0.0345(16) 0.0466(18) -0.0129(14) 0.0010(14) -0.0104(13) N5 0.0475(19) 0.0444(19) 0.065(2) -0.0163(18) 0.0134(17) -0.0132(15) N6 0.065(2) 0.0318(16) 0.047(2) -0.0115(15) 0.0025(17) -0.0123(16) N7 0.052(2) 0.066(3) 0.094(4) -0.007(3) -0.012(2) -0.015(2) O1 0.0587(19) 0.0589(19) 0.087(2) -0.0122(18) -0.0274(17) -0.0130(15) O2 0.089(3) 0.121(4) 0.095(3) -0.038(3) 0.009(2) -0.046(3) O3 0.145(4) 0.184(5) 0.121(4) -0.045(4) 0.067(4) -0.110(4) O4 0.124(4) 0.068(3) 0.160(5) -0.027(3) 0.035(3) -0.027(3) O5 0.069(2) 0.0493(17) 0.081(2) -0.0245(17) -0.0226(17) -0.0001(16) O6 0.114(3) 0.065(2) 0.071(2) -0.040(2) 0.001(2) -0.012(2) O7 0.0499(16) 0.0447(15) 0.0574(18) -0.0185(14) -0.0011(14) -0.0009(13) _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 C1 N1 1.338(5) . ? C1 C2 1.400(6) . ? C1 H1 0.9300 . ? C2 C3 1.363(6) . ? C2 H2 0.9300 . ? C3 C4 1.404(6) . ? C3 H3 0.9300 . ? C4 C5 1.401(5) . ? C4 C6 1.422(6) . ? C5 N1 1.360(5) . ? C5 C9 1.427(5) . ? C6 C7 1.346(7) . ? C6 H6 0.9300 . ? C7 C8 1.435(6) . ? C7 H7 0.9300 . ? C8 C9 1.379(5) . ? C8 C10 1.410(6) . ? C9 N2 1.349(5) . ? C10 C11 1.371(6) . ? C10 H10 0.9300 . ? C11 C12 1.395(5) . ? C11 H11 0.9300 . ? C12 N2 1.317(5) . ? C12 N3 1.387(5) . ? C13 N3 1.349(5) . ? C13 C14 1.356(6) . ? C13 H13 0.9300 . ? C14 C15 1.416(6) . ? C14 H14 0.9300 . ? C15 N5 1.317(5) . ? C15 N4 1.340(5) . ? C16 O1 1.406(6) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? Cu1 N2 1.923(3) . ? Cu1 O7 1.957(3) . ? Cu1 N4 2.035(4) . ? Cu1 N1 2.069(4) . ? Cu1 O1 2.206(4) . ? N3 N4 1.389(4) . ? N5 H5A 0.8600 . ? N5 H5B 0.8600 . ? N6 O6 1.213(4) . ? N6 O5 1.219(4) . ? N6 O7 1.301(4) . ? N7 O3 1.165(6) . ? N7 O4 1.200(6) . ? N7 O2 1.283(6) . ? O1 H4 0.9352 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 121.0(4) . . ? N1 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C3 C2 C1 121.1(4) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 119.8(4) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 115.5(4) . . ? C5 C4 C6 117.8(4) . . ? C3 C4 C6 126.6(4) . . ? N1 C5 C4 125.2(4) . . ? N1 C5 C9 115.7(3) . . ? C4 C5 C9 119.1(4) . . ? C7 C6 C4 122.6(4) . . ? C7 C6 H6 118.7 . . ? C4 C6 H6 118.7 . . ? C6 C7 C8 120.8(4) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C9 C8 C10 115.6(4) . . ? C9 C8 C7 117.4(4) . . ? C10 C8 C7 126.9(4) . . ? N2 C9 C8 123.5(4) . . ? N2 C9 C5 114.3(3) . . ? C8 C9 C5 122.2(4) . . ? C11 C10 C8 121.1(4) . . ? C11 C10 H10 119.5 . . ? C8 C10 H10 119.4 . . ? C10 C11 C12 118.6(4) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? N2 C12 N3 111.5(3) . . ? N2 C12 C11 121.3(4) . . ? N3 C12 C11 127.2(4) . . ? N3 C13 C14 108.0(3) . . ? N3 C13 H13 126.0 . . ? C14 C13 H13 126.0 . . ? C13 C14 C15 106.1(3) . . ? C13 C14 H14 126.9 . . ? C15 C14 H14 126.9 . . ? N5 C15 N4 122.4(4) . . ? N5 C15 C14 127.6(4) . . ? N4 C15 C14 110.0(3) . . ? O1 C16 H16A 109.5 . . ? O1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 Cu1 O7 164.90(12) . . ? N2 Cu1 N4 77.84(15) . . ? O7 Cu1 N4 103.43(15) . . ? N2 Cu1 N1 80.16(16) . . ? O7 Cu1 N1 97.10(15) . . ? N4 Cu1 N1 157.82(13) . . ? N2 Cu1 O1 102.59(15) . . ? O7 Cu1 O1 92.39(15) . . ? N4 Cu1 O1 93.54(13) . . ? N1 Cu1 O1 93.92(15) . . ? C1 N1 C5 117.4(4) . . ? C1 N1 Cu1 130.7(3) . . ? C5 N1 Cu1 111.8(3) . . ? C12 N2 C9 120.0(3) . . ? C12 N2 Cu1 122.0(3) . . ? C9 N2 Cu1 118.0(3) . . ? C13 N3 C12 132.9(3) . . ? C13 N3 N4 110.6(3) . . ? C12 N3 N4 116.4(3) . . ? C15 N4 N3 105.2(3) . . ? C15 N4 Cu1 142.4(3) . . ? N3 N4 Cu1 112.2(2) . . ? C15 N5 H5A 120.0 . . ? C15 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? O6 N6 O5 124.1(4) . . ? O6 N6 O7 118.6(3) . . ? O5 N6 O7 117.3(3) . . ? O3 N7 O4 126.6(6) . . ? O3 N7 O2 118.3(5) . . ? O4 N7 O2 115.0(5) . . ? C16 O1 Cu1 132.1(3) . . ? C16 O1 H4 111.7 . . ? Cu1 O1 H4 110.4 . . ? N6 O7 Cu1 108.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 1.0(6) . . . . ? C1 C2 C3 C4 -2.0(7) . . . . ? C2 C3 C4 C5 0.7(6) . . . . ? C2 C3 C4 C6 -178.1(4) . . . . ? C3 C4 C5 N1 1.6(6) . . . . ? C6 C4 C5 N1 -179.5(4) . . . . ? C3 C4 C5 C9 -178.2(3) . . . . ? C6 C4 C5 C9 0.8(5) . . . . ? C5 C4 C6 C7 0.1(6) . . . . ? C3 C4 C6 C7 178.9(4) . . . . ? C4 C6 C7 C8 0.1(6) . . . . ? C6 C7 C8 C9 -1.2(6) . . . . ? C6 C7 C8 C10 -178.9(4) . . . . ? C10 C8 C9 N2 -0.3(5) . . . . ? C7 C8 C9 N2 -178.3(3) . . . . ? C10 C8 C9 C5 -180.0(3) . . . . ? C7 C8 C9 C5 2.1(5) . . . . ? N1 C5 C9 N2 -1.4(5) . . . . ? C4 C5 C9 N2 178.4(3) . . . . ? N1 C5 C9 C8 178.3(3) . . . . ? C4 C5 C9 C8 -1.9(5) . . . . ? C9 C8 C10 C11 1.0(6) . . . . ? C7 C8 C10 C11 178.7(4) . . . . ? C8 C10 C11 C12 -0.9(6) . . . . ? C10 C11 C12 N2 0.0(6) . . . . ? C10 C11 C12 N3 177.8(3) . . . . ? N3 C13 C14 C15 -0.1(4) . . . . ? C13 C14 C15 N5 178.9(4) . . . . ? C13 C14 C15 N4 0.8(4) . . . . ? C2 C1 N1 C5 1.1(6) . . . . ? C2 C1 N1 Cu1 177.0(3) . . . . ? C4 C5 N1 C1 -2.5(5) . . . . ? C9 C5 N1 C1 177.3(3) . . . . ? C4 C5 N1 Cu1 -179.1(3) . . . . ? C9 C5 N1 Cu1 0.6(4) . . . . ? N2 Cu1 N1 C1 -176.0(4) . . . . ? O7 Cu1 N1 C1 19.1(4) . . . . ? N4 Cu1 N1 C1 176.8(3) . . . . ? O1 Cu1 N1 C1 -73.8(4) . . . . ? N2 Cu1 N1 C5 0.1(2) . . . . ? O7 Cu1 N1 C5 -164.9(2) . . . . ? N4 Cu1 N1 C5 -7.2(5) . . . . ? O1 Cu1 N1 C5 102.2(3) . . . . ? N3 C12 N2 C9 -177.4(3) . . . . ? C11 C12 N2 C9 0.6(5) . . . . ? N3 C12 N2 Cu1 0.2(4) . . . . ? C11 C12 N2 Cu1 178.2(3) . . . . ? C8 C9 N2 C12 -0.5(5) . . . . ? C5 C9 N2 C12 179.2(3) . . . . ? C8 C9 N2 Cu1 -178.2(3) . . . . ? C5 C9 N2 Cu1 1.5(4) . . . . ? O7 Cu1 N2 C12 -97.9(5) . . . . ? N4 Cu1 N2 C12 -1.4(3) . . . . ? N1 Cu1 N2 C12 -178.6(3) . . . . ? O1 Cu1 N2 C12 89.6(3) . . . . ? O7 Cu1 N2 C9 79.8(5) . . . . ? N4 Cu1 N2 C9 176.3(3) . . . . ? N1 Cu1 N2 C9 -0.9(3) . . . . ? O1 Cu1 N2 C9 -92.8(3) . . . . ? C14 C13 N3 C12 179.5(4) . . . . ? C14 C13 N3 N4 -0.6(4) . . . . ? N2 C12 N3 C13 -178.3(4) . . . . ? C11 C12 N3 C13 3.8(6) . . . . ? N2 C12 N3 N4 1.9(4) . . . . ? C11 C12 N3 N4 -176.1(3) . . . . ? N5 C15 N4 N3 -179.3(3) . . . . ? C14 C15 N4 N3 -1.2(4) . . . . ? N5 C15 N4 Cu1 6.6(6) . . . . ? C14 C15 N4 Cu1 -175.2(3) . . . . ? C13 N3 N4 C15 1.1(4) . . . . ? C12 N3 N4 C15 -179.0(3) . . . . ? C13 N3 N4 Cu1 177.2(2) . . . . ? C12 N3 N4 Cu1 -2.9(4) . . . . ? N2 Cu1 N4 C15 176.0(4) . . . . ? O7 Cu1 N4 C15 -19.4(4) . . . . ? N1 Cu1 N4 C15 -176.7(4) . . . . ? O1 Cu1 N4 C15 73.9(4) . . . . ? N2 Cu1 N4 N3 2.2(2) . . . . ? O7 Cu1 N4 N3 166.8(2) . . . . ? N1 Cu1 N4 N3 9.5(5) . . . . ? O1 Cu1 N4 N3 -99.9(3) . . . . ? N2 Cu1 O1 C16 145.0(4) . . . . ? O7 Cu1 O1 C16 -33.0(5) . . . . ? N4 Cu1 O1 C16 -136.7(5) . . . . ? N1 Cu1 O1 C16 64.2(5) . . . . ? O6 N6 O7 Cu1 -172.7(3) . . . . ? O5 N6 O7 Cu1 7.4(4) . . . . ? N2 Cu1 O7 N6 10.0(6) . . . . ? N4 Cu1 O7 N6 -83.0(3) . . . . ? N1 Cu1 O7 N6 88.5(3) . . . . ? O1 Cu1 O7 N6 -177.2(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5A O7 0.86 2.54 3.138(5) 127.4 2_766 N5 H5B O4 0.86 2.15 2.985(7) 163.8 2_776 O1 H4 O2 0.94 1.83 2.758(6) 170.9 . O1 H4 N7 0.94 2.65 3.469(7) 147.0 . _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.744 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.087 _database_code_depnum_ccdc_archive 'CCDC 839722' ####################################################################### # # 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_111019am #TrackingRef 'Check-111019am.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 Cl2 Cu N5' _chemical_formula_weight 395.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.7867(16) _cell_length_b 11.215(2) _cell_length_c 16.845(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.343(3) _cell_angle_gamma 90.00 _cell_volume 1469.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1539 _cell_measurement_theta_min 2.182 _cell_measurement_theta_max 22.862 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.788 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 796 _exptl_absorpt_coefficient_mu 1.854 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5884 _exptl_absorpt_correction_T_max 0.9130 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 Smart APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8404 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3191 _reflns_number_gt 2490 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Bruker, 2001)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0458P)^2^+1.0639P] 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 3191 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.1084 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 C1 C 0.6451(5) 0.1195(4) 0.1335(2) 0.0398(10) Uani 1 1 d . . . H1 H 0.6395 0.1283 0.1882 0.048 Uiso 1 1 calc R . . C2 C 0.7494(5) 0.0300(4) 0.1039(3) 0.0426(11) Uani 1 1 d . . . H2 H 0.8114 -0.0195 0.1389 0.051 Uiso 1 1 calc R . . C3 C 0.7607(5) 0.0148(4) 0.0241(3) 0.0383(10) Uani 1 1 d . . . H3 H 0.8310 -0.0444 0.0044 0.046 Uiso 1 1 calc R . . C4 C 0.6655(5) 0.0890(4) -0.0278(2) 0.0335(9) Uani 1 1 d . . . C5 C 0.5649(5) 0.1759(3) 0.0064(2) 0.0284(8) Uani 1 1 d . . . C6 C 0.4711(5) 0.2580(3) -0.0423(2) 0.0281(8) Uani 1 1 d . . . C7 C 0.4740(5) 0.2542(4) -0.1250(2) 0.0334(9) Uani 1 1 d . . . C8 C 0.5756(6) 0.1627(4) -0.1588(2) 0.0428(11) Uani 1 1 d . . . H8 H 0.5795 0.1569 -0.2138 0.051 Uiso 1 1 calc R . . C9 C 0.6656(6) 0.0848(4) -0.1130(2) 0.0415(11) Uani 1 1 d . . . H9 H 0.7301 0.0264 -0.1372 0.050 Uiso 1 1 calc R . . C10 C 0.3830(5) 0.3459(4) -0.1658(2) 0.0387(10) Uani 1 1 d . . . H10 H 0.3807 0.3476 -0.2210 0.046 Uiso 1 1 calc R . . C11 C 0.2988(5) 0.4317(4) -0.1259(2) 0.0353(10) Uani 1 1 d . . . H11 H 0.2385 0.4916 -0.1532 0.042 Uiso 1 1 calc R . . C12 C 0.3048(5) 0.4280(4) -0.0421(2) 0.0293(9) Uani 1 1 d . . . C13 C 0.1370(5) 0.6108(4) -0.0047(3) 0.0371(10) Uani 1 1 d . . . H13 H 0.1013 0.6419 -0.0538 0.045 Uiso 1 1 calc R . . C14 C 0.1019(5) 0.6559(4) 0.0670(3) 0.0388(10) Uani 1 1 d . . . H14 H 0.0370 0.7235 0.0768 0.047 Uiso 1 1 calc R . . C15 C 0.1827(5) 0.5808(4) 0.1241(2) 0.0351(9) Uani 1 1 d . . . Cl1 Cl 0.48497(15) 0.35917(10) 0.23886(6) 0.0424(3) Uani 1 1 d . . . Cl2 Cl 0.12537(13) 0.21385(9) 0.13053(6) 0.0385(3) Uani 1 1 d . . . Cu1 Cu 0.38612(6) 0.33068(4) 0.11286(3) 0.02940(16) Uani 1 1 d . . . N1 N 0.5544(4) 0.1921(3) 0.08668(18) 0.0299(7) Uani 1 1 d . . . N2 N 0.3852(4) 0.3424(3) -0.00367(17) 0.0278(7) Uani 1 1 d . . . N3 N 0.2342(4) 0.5111(3) 0.00800(18) 0.0314(7) Uani 1 1 d . . . N4 N 0.2647(4) 0.4921(3) 0.08891(18) 0.0327(8) Uani 1 1 d . . . N5 N 0.1835(5) 0.5883(3) 0.2036(2) 0.0502(10) Uani 1 1 d . . . H5A H 0.2370 0.5356 0.2323 0.060 Uiso 1 1 calc R . . H5B H 0.1304 0.6457 0.2259 0.060 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 C1 0.043(3) 0.044(3) 0.032(2) 0.0040(19) -0.0047(19) -0.003(2) C2 0.038(3) 0.040(3) 0.049(3) 0.008(2) -0.006(2) 0.000(2) C3 0.030(2) 0.028(2) 0.057(3) -0.002(2) 0.009(2) 0.0004(18) C4 0.028(2) 0.031(2) 0.041(2) -0.0035(18) 0.0065(18) -0.0093(17) C5 0.026(2) 0.029(2) 0.031(2) 0.0029(17) 0.0022(16) -0.0084(17) C6 0.029(2) 0.029(2) 0.0268(19) 0.0035(16) 0.0040(16) -0.0096(17) C7 0.038(2) 0.037(2) 0.0255(19) -0.0001(17) 0.0035(17) -0.0123(19) C8 0.056(3) 0.044(3) 0.029(2) -0.007(2) 0.009(2) -0.013(2) C9 0.044(3) 0.038(3) 0.044(2) -0.009(2) 0.015(2) -0.008(2) C10 0.041(3) 0.052(3) 0.0228(19) 0.0057(19) -0.0017(17) -0.011(2) C11 0.032(2) 0.045(3) 0.028(2) 0.0163(19) -0.0067(17) -0.010(2) C12 0.024(2) 0.034(2) 0.030(2) 0.0049(17) -0.0020(16) -0.0105(17) C13 0.029(2) 0.027(2) 0.055(3) 0.010(2) -0.005(2) -0.0061(18) C14 0.029(2) 0.022(2) 0.067(3) -0.002(2) 0.006(2) 0.0011(17) C15 0.033(2) 0.031(2) 0.042(2) -0.0045(19) 0.0062(18) -0.0066(18) Cl1 0.0572(7) 0.0434(6) 0.0261(5) 0.0000(4) -0.0038(5) -0.0119(5) Cl2 0.0361(6) 0.0360(6) 0.0432(6) 0.0051(5) 0.0000(5) -0.0078(5) Cu1 0.0351(3) 0.0306(3) 0.0225(2) 0.0022(2) 0.00080(19) -0.0032(2) N1 0.0295(18) 0.0336(19) 0.0263(16) 0.0054(14) -0.0011(14) -0.0053(14) N2 0.0297(18) 0.0298(18) 0.0237(15) 0.0012(14) -0.0002(13) -0.0054(14) N3 0.0313(18) 0.0305(19) 0.0322(17) 0.0036(14) 0.0005(14) -0.0056(15) N4 0.0349(19) 0.0319(19) 0.0313(17) 0.0034(15) -0.0005(14) -0.0039(15) N5 0.066(3) 0.039(2) 0.047(2) -0.0069(18) 0.017(2) 0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.318(5) . ? C1 C2 1.396(6) . ? C1 H1 0.9300 . ? C2 C3 1.361(6) . ? C2 H2 0.9300 . ? C3 C4 1.398(6) . ? C3 H3 0.9300 . ? C4 C5 1.390(5) . ? C4 C9 1.436(5) . ? C5 N1 1.370(5) . ? C5 C6 1.417(5) . ? C6 N2 1.343(5) . ? C6 C7 1.394(5) . ? C7 C10 1.411(6) . ? C7 C8 1.428(6) . ? C8 C9 1.344(6) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.358(6) . ? C10 H10 0.9300 . ? C11 C12 1.411(5) . ? C11 H11 0.9300 . ? C12 N2 1.303(5) . ? C12 N3 1.385(5) . ? C13 C14 1.347(6) . ? C13 N3 1.362(5) . ? C13 H13 0.9300 . ? C14 C15 1.407(6) . ? C14 H14 0.9300 . ? C15 N4 1.334(5) . ? C15 N5 1.342(5) . ? Cl1 Cu1 2.2507(11) . ? Cl2 Cu1 2.4448(11) . ? Cu1 N2 1.967(3) . ? Cu1 N4 2.074(3) . ? Cu1 N1 2.092(3) . ? N3 N4 1.390(4) . ? N5 H5A 0.8600 . ? N5 H5B 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 122.4(4) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 120.3(4) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.3(4) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 116.9(4) . . ? C5 C4 C9 117.4(4) . . ? C3 C4 C9 125.7(4) . . ? N1 C5 C4 124.0(4) . . ? N1 C5 C6 115.9(3) . . ? C4 C5 C6 120.1(4) . . ? N2 C6 C7 122.3(4) . . ? N2 C6 C5 115.6(3) . . ? C7 C6 C5 122.0(4) . . ? C6 C7 C10 115.8(4) . . ? C6 C7 C8 116.9(4) . . ? C10 C7 C8 127.2(4) . . ? C9 C8 C7 121.5(4) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C4 122.1(4) . . ? C8 C9 H9 118.9 . . ? C4 C9 H9 118.9 . . ? C11 C10 C7 121.2(4) . . ? C11 C10 H10 119.4 . . ? C7 C10 H10 119.4 . . ? C10 C11 C12 118.5(4) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? N2 C12 N3 112.8(3) . . ? N2 C12 C11 120.9(4) . . ? N3 C12 C11 126.3(4) . . ? C14 C13 N3 107.4(4) . . ? C14 C13 H13 126.3 . . ? N3 C13 H13 126.3 . . ? C13 C14 C15 106.6(4) . . ? C13 C14 H14 126.7 . . ? C15 C14 H14 126.7 . . ? N4 C15 N5 120.5(4) . . ? N4 C15 C14 110.6(4) . . ? N5 C15 C14 128.9(4) . . ? N2 Cu1 N4 76.37(13) . . ? N2 Cu1 N1 79.41(13) . . ? N4 Cu1 N1 153.14(12) . . ? N2 Cu1 Cl1 156.74(10) . . ? N4 Cu1 Cl1 101.26(9) . . ? N1 Cu1 Cl1 96.39(9) . . ? N2 Cu1 Cl2 100.84(9) . . ? N4 Cu1 Cl2 96.72(9) . . ? N1 Cu1 Cl2 99.09(9) . . ? Cl1 Cu1 Cl2 102.42(4) . . ? C1 N1 C5 117.2(3) . . ? C1 N1 Cu1 131.1(3) . . ? C5 N1 Cu1 111.7(2) . . ? C12 N2 C6 121.1(3) . . ? C12 N2 Cu1 121.8(3) . . ? C6 N2 Cu1 117.1(2) . . ? C13 N3 C12 133.5(3) . . ? C13 N3 N4 110.5(3) . . ? C12 N3 N4 116.0(3) . . ? C15 N4 N3 104.8(3) . . ? C15 N4 Cu1 141.9(3) . . ? N3 N4 Cu1 112.5(2) . . ? C15 N5 H5A 120.0 . . ? C15 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.1(7) . . . . ? C1 C2 C3 C4 -0.6(6) . . . . ? C2 C3 C4 C5 0.6(6) . . . . ? C2 C3 C4 C9 179.2(4) . . . . ? C3 C4 C5 N1 -0.1(6) . . . . ? C9 C4 C5 N1 -178.8(4) . . . . ? C3 C4 C5 C6 177.0(3) . . . . ? C9 C4 C5 C6 -1.7(5) . . . . ? N1 C5 C6 N2 0.7(5) . . . . ? C4 C5 C6 N2 -176.6(3) . . . . ? N1 C5 C6 C7 178.2(3) . . . . ? C4 C5 C6 C7 0.8(6) . . . . ? N2 C6 C7 C10 1.0(6) . . . . ? C5 C6 C7 C10 -176.3(4) . . . . ? N2 C6 C7 C8 177.6(4) . . . . ? C5 C6 C7 C8 0.4(6) . . . . ? C6 C7 C8 C9 -0.7(6) . . . . ? C10 C7 C8 C9 175.5(4) . . . . ? C7 C8 C9 C4 -0.1(7) . . . . ? C5 C4 C9 C8 1.3(6) . . . . ? C3 C4 C9 C8 -177.2(4) . . . . ? C6 C7 C10 C11 0.0(6) . . . . ? C8 C7 C10 C11 -176.2(4) . . . . ? C7 C10 C11 C12 0.4(6) . . . . ? C10 C11 C12 N2 -1.9(6) . . . . ? C10 C11 C12 N3 176.5(4) . . . . ? N3 C13 C14 C15 0.6(4) . . . . ? C13 C14 C15 N4 -0.1(5) . . . . ? C13 C14 C15 N5 -179.2(4) . . . . ? C2 C1 N1 C5 0.5(6) . . . . ? C2 C1 N1 Cu1 178.9(3) . . . . ? C4 C5 N1 C1 -0.5(6) . . . . ? C6 C5 N1 C1 -177.7(3) . . . . ? C4 C5 N1 Cu1 -179.2(3) . . . . ? C6 C5 N1 Cu1 3.6(4) . . . . ? N2 Cu1 N1 C1 176.7(4) . . . . ? N4 Cu1 N1 C1 150.9(3) . . . . ? Cl1 Cu1 N1 C1 19.9(4) . . . . ? Cl2 Cu1 N1 C1 -83.8(4) . . . . ? N2 Cu1 N1 C5 -4.8(2) . . . . ? N4 Cu1 N1 C5 -30.7(4) . . . . ? Cl1 Cu1 N1 C5 -161.7(2) . . . . ? Cl2 Cu1 N1 C5 94.6(2) . . . . ? N3 C12 N2 C6 -175.6(3) . . . . ? C11 C12 N2 C6 2.9(5) . . . . ? N3 C12 N2 Cu1 4.4(4) . . . . ? C11 C12 N2 Cu1 -177.0(3) . . . . ? C7 C6 N2 C12 -2.5(6) . . . . ? C5 C6 N2 C12 174.9(3) . . . . ? C7 C6 N2 Cu1 177.4(3) . . . . ? C5 C6 N2 Cu1 -5.2(4) . . . . ? N4 Cu1 N2 C12 -6.3(3) . . . . ? N1 Cu1 N2 C12 -174.6(3) . . . . ? Cl1 Cu1 N2 C12 -93.1(4) . . . . ? Cl2 Cu1 N2 C12 88.0(3) . . . . ? N4 Cu1 N2 C6 173.8(3) . . . . ? N1 Cu1 N2 C6 5.5(3) . . . . ? Cl1 Cu1 N2 C6 87.0(4) . . . . ? Cl2 Cu1 N2 C6 -91.9(3) . . . . ? C14 C13 N3 C12 178.7(4) . . . . ? C14 C13 N3 N4 -0.8(4) . . . . ? N2 C12 N3 C13 -177.6(4) . . . . ? C11 C12 N3 C13 3.9(7) . . . . ? N2 C12 N3 N4 1.9(5) . . . . ? C11 C12 N3 N4 -176.6(3) . . . . ? N5 C15 N4 N3 178.9(4) . . . . ? C14 C15 N4 N3 -0.3(4) . . . . ? N5 C15 N4 Cu1 10.6(7) . . . . ? C14 C15 N4 Cu1 -168.6(3) . . . . ? C13 N3 N4 C15 0.7(4) . . . . ? C12 N3 N4 C15 -178.9(3) . . . . ? C13 N3 N4 Cu1 172.9(2) . . . . ? C12 N3 N4 Cu1 -6.7(4) . . . . ? N2 Cu1 N4 C15 174.3(5) . . . . ? N1 Cu1 N4 C15 -159.5(4) . . . . ? Cl1 Cu1 N4 C15 -29.4(4) . . . . ? Cl2 Cu1 N4 C15 74.8(4) . . . . ? N2 Cu1 N4 N3 6.6(2) . . . . ? N1 Cu1 N4 N3 32.8(4) . . . . ? Cl1 Cu1 N4 N3 162.9(2) . . . . ? Cl2 Cu1 N4 N3 -93.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.989 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.094 _database_code_depnum_ccdc_archive 'CCDC 870050'