# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Huang, Wei' _publ_contact_author_email whuang@nju.edu.cn _publ_section_title ; The first observation of azo-hydrazone and cis-trans tautomerisms for Disperse Yellow dyes and their nickel(II) and copper(II) complexes ; _publ_author_name 'Wei Huang' # Attachment '- 1-5-OK.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 760909' #TrackingRef '- 1-5-OK.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 Cl2 N4 O2' _chemical_formula_sum 'C15 H12 Cl2 N4 O2' _chemical_formula_weight 351.19 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.3689(16) _cell_length_b 20.067(4) _cell_length_c 21.444(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.617(4) _cell_angle_gamma 90.00 _cell_volume 3160.5(12) _cell_formula_units_Z 8 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 649 _cell_measurement_theta_min 2.243 _cell_measurement_theta_max 16.774 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.425 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9012 _exptl_absorpt_correction_T_max 0.9668 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15882 _diffrn_reflns_av_R_equivalents 0.1415 _diffrn_reflns_av_sigmaI/netI 0.3013 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5571 _reflns_number_gt 1416 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (BRUKER 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0106P)^2^] 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 5571 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2379 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1069 _refine_ls_wR_factor_gt 0.0811 _refine_ls_goodness_of_fit_ref 0.667 _refine_ls_restrained_S_all 0.667 _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 0.2839(8) 0.5238(3) 0.6196(3) 0.0416(17) Uani 1 1 d . . . C2 C 0.2410(8) 0.5880(3) 0.6480(3) 0.0470(18) Uani 1 1 d . . . C3 C 0.3391(8) 0.5429(3) 0.7506(3) 0.0473(18) Uani 1 1 d . . . C4 C 0.3753(7) 0.4797(3) 0.7206(3) 0.0433(17) Uani 1 1 d . . . C5 C 0.3487(8) 0.4693(3) 0.6587(3) 0.0437(17) Uani 1 1 d . . . C6 C 0.2360(9) 0.6605(3) 0.7386(3) 0.071(2) Uani 1 1 d . . . H6A H 0.2200 0.6561 0.7828 0.085 Uiso 1 1 calc R . . H6B H 0.1246 0.6785 0.7181 0.085 Uiso 1 1 calc R . . C7 C 0.3967(9) 0.7085(3) 0.7292(3) 0.092(3) Uani 1 1 d . . . H7A H 0.5060 0.6912 0.7507 0.138 Uiso 1 1 calc R . . H7B H 0.3705 0.7516 0.7458 0.138 Uiso 1 1 calc R . . H7C H 0.4129 0.7123 0.6854 0.138 Uiso 1 1 calc R . . C8 C 0.4431(9) 0.4278(3) 0.7619(3) 0.0511(19) Uani 1 1 d . . . C9 C 0.3903(7) 0.4031(2) 0.6299(2) 0.0589(19) Uani 1 1 d . . . H9A H 0.4557 0.3755 0.6607 0.088 Uiso 1 1 calc R . . H9B H 0.4632 0.4101 0.5953 0.088 Uiso 1 1 calc R . . H9C H 0.2786 0.3815 0.6154 0.088 Uiso 1 1 calc R . . C10 C 0.1819(8) 0.5482(3) 0.4548(3) 0.0492(18) Uani 1 1 d . . . C11 C 0.2269(8) 0.4875(3) 0.4304(3) 0.060(2) Uani 1 1 d . . . H11 H 0.2732 0.4531 0.4560 0.072 Uiso 1 1 calc R . . C12 C 0.1998(8) 0.4800(3) 0.3652(3) 0.0532(19) Uani 1 1 d . . . C13 C 0.1351(8) 0.5317(3) 0.3279(3) 0.0539(18) Uani 1 1 d . . . C14 C 0.0951(8) 0.5923(3) 0.3509(3) 0.061(2) Uani 1 1 d . . . H14 H 0.0529 0.6268 0.3246 0.073 Uiso 1 1 calc R . . C15 C 0.1200(8) 0.6010(3) 0.4167(3) 0.0518(18) Uani 1 1 d . . . H15 H 0.0951 0.6420 0.4343 0.062 Uiso 1 1 calc R . . C16 C 0.1691(8) 0.0800(3) 0.5080(3) 0.0424(17) Uani 1 1 d . . . C17 C 0.1077(9) 0.1041(3) 0.4468(3) 0.0514(19) Uani 1 1 d . . . C18 C 0.0345(8) 0.2114(3) 0.4941(3) 0.0522(19) Uani 1 1 d . . . C19 C 0.0909(8) 0.1832(3) 0.5562(3) 0.0434(17) Uani 1 1 d . . . C20 C 0.1549(8) 0.1198(3) 0.5628(3) 0.0425(17) Uani 1 1 d . . . C21 C -0.0262(8) 0.1942(3) 0.3801(3) 0.062(2) Uani 1 1 d . . . H21A H -0.1058 0.2319 0.3853 0.074 Uiso 1 1 calc R . . H21B H -0.0977 0.1595 0.3583 0.074 Uiso 1 1 calc R . . C22 C 0.1226(8) 0.2149(3) 0.3410(3) 0.082(2) Uani 1 1 d . . . H22A H 0.1859 0.2524 0.3601 0.123 Uiso 1 1 calc R . . H22B H 0.0715 0.2270 0.3000 0.123 Uiso 1 1 calc R . . H22C H 0.2062 0.1786 0.3378 0.123 Uiso 1 1 calc R . . C23 C 0.0736(10) 0.2260(3) 0.6088(3) 0.062(2) Uani 1 1 d . . . C24 C 0.2059(8) 0.0907(2) 0.6271(2) 0.072(2) Uani 1 1 d . . . H24A H 0.1864 0.1234 0.6585 0.108 Uiso 1 1 calc R . . H24B H 0.3318 0.0779 0.6302 0.108 Uiso 1 1 calc R . . H24C H 0.1317 0.0523 0.6333 0.108 Uiso 1 1 calc R . . C25 C 0.3362(8) -0.0864(3) 0.4869(3) 0.0419(16) Uani 1 1 d . . . C26 C 0.3536(7) -0.1295(3) 0.4380(3) 0.0468(18) Uani 1 1 d . . . H26 H 0.3226 -0.1160 0.3970 0.056 Uiso 1 1 calc R . . C27 C 0.4178(8) -0.1929(3) 0.4506(3) 0.0506(18) Uani 1 1 d . . . C28 C 0.4609(8) -0.2129(3) 0.5110(3) 0.0432(17) Uani 1 1 d . . . C29 C 0.4486(8) -0.1686(3) 0.5594(3) 0.0507(18) Uani 1 1 d . . . H29 H 0.4824 -0.1820 0.6002 0.061 Uiso 1 1 calc R . . C30 C 0.3867(7) -0.1044(3) 0.5481(3) 0.0472(18) Uani 1 1 d . . . H30 H 0.3791 -0.0742 0.5807 0.057 Uiso 1 1 calc R . . Cl1 Cl 0.1000(3) 0.52023(8) 0.24769(7) 0.0866(7) Uani 1 1 d . . . Cl2 Cl 0.2594(3) 0.40403(8) 0.33479(8) 0.0889(7) Uani 1 1 d . . . Cl3 Cl 0.4344(2) -0.24631(8) 0.38886(8) 0.0816(6) Uani 1 1 d . . . Cl4 Cl 0.5351(2) -0.29284(7) 0.52731(8) 0.0773(6) Uani 1 1 d . . . N1 N 0.2730(6) 0.5944(2) 0.7121(2) 0.0483(14) Uani 1 1 d . . . N2 N 0.5013(8) 0.3873(3) 0.7950(3) 0.081(2) Uani 1 1 d . . . N3 N 0.2638(6) 0.5121(2) 0.5591(2) 0.0474(14) Uani 1 1 d . . . N4 N 0.2063(6) 0.5596(2) 0.5198(2) 0.0483(14) Uani 1 1 d . . . H4 H 0.1831 0.5984 0.5342 0.058 Uiso 1 1 calc R . . N5 N 0.0431(6) 0.1693(2) 0.4424(2) 0.0486(15) Uani 1 1 d . . . N6 N 0.0619(9) 0.2566(3) 0.6525(3) 0.091(2) Uani 1 1 d . . . N7 N 0.2420(6) 0.0195(2) 0.5190(2) 0.0469(14) Uani 1 1 d . . . N8 N 0.2659(6) -0.0212(2) 0.4733(2) 0.0495(15) Uani 1 1 d . . . H8 H 0.2396 -0.0090 0.4352 0.059 Uiso 1 1 calc R . . O1 O 0.1814(6) 0.63523(17) 0.61582(18) 0.0652(14) Uani 1 1 d . . . O2 O 0.3616(6) 0.55165(18) 0.80718(18) 0.0657(14) Uani 1 1 d . . . O3 O 0.1115(6) 0.06997(18) 0.39910(18) 0.0617(14) Uani 1 1 d . . . O4 O -0.0241(6) 0.2678(2) 0.48861(19) 0.0704(15) 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(5) 0.036(4) 0.044(4) -0.005(4) 0.000(4) 0.005(3) C2 0.048(5) 0.042(4) 0.050(5) -0.003(4) 0.003(4) 0.006(4) C3 0.056(5) 0.034(4) 0.050(4) 0.001(4) -0.001(4) 0.000(3) C4 0.036(4) 0.042(4) 0.052(4) 0.011(4) 0.002(4) 0.005(3) C5 0.050(5) 0.028(4) 0.053(4) -0.001(3) 0.001(4) -0.003(3) C6 0.120(7) 0.051(4) 0.041(4) -0.007(4) 0.006(4) 0.043(4) C7 0.147(8) 0.043(4) 0.087(6) 0.002(4) 0.015(5) -0.018(5) C8 0.057(5) 0.041(4) 0.054(5) -0.006(4) -0.001(4) -0.008(4) C9 0.068(5) 0.040(4) 0.070(5) -0.011(4) 0.015(4) 0.007(4) C10 0.051(5) 0.049(5) 0.048(5) -0.013(4) 0.012(4) -0.004(4) C11 0.052(5) 0.065(5) 0.060(5) -0.011(4) -0.010(4) 0.011(4) C12 0.051(5) 0.038(4) 0.070(5) -0.028(4) 0.010(4) -0.002(4) C13 0.050(5) 0.068(5) 0.046(4) -0.004(4) 0.020(4) -0.004(4) C14 0.060(5) 0.053(5) 0.071(5) -0.023(4) 0.012(4) -0.007(4) C15 0.061(5) 0.036(4) 0.058(5) -0.002(4) 0.004(4) -0.005(3) C16 0.042(5) 0.036(4) 0.049(4) 0.001(4) 0.004(4) 0.001(3) C17 0.050(5) 0.051(5) 0.051(5) 0.012(4) -0.005(4) -0.003(4) C18 0.050(5) 0.051(5) 0.057(5) 0.003(4) 0.013(4) 0.002(4) C19 0.045(5) 0.046(4) 0.039(4) 0.006(4) 0.007(4) 0.005(3) C20 0.036(4) 0.041(4) 0.050(4) 0.015(4) 0.004(4) 0.002(3) C21 0.058(5) 0.053(4) 0.074(5) 0.020(4) 0.008(4) 0.025(4) C22 0.093(7) 0.083(5) 0.070(5) 0.028(4) 0.013(5) 0.017(5) C23 0.070(6) 0.056(5) 0.059(5) 0.024(4) 0.005(5) 0.024(4) C24 0.099(6) 0.054(4) 0.062(5) 0.012(4) 0.001(4) 0.014(4) C25 0.041(5) 0.030(4) 0.055(5) 0.015(4) 0.002(4) 0.004(3) C26 0.054(5) 0.046(4) 0.040(4) 0.005(4) 0.003(4) -0.004(4) C27 0.052(5) 0.036(4) 0.064(5) -0.009(4) 0.007(4) 0.003(4) C28 0.039(5) 0.033(4) 0.057(5) 0.009(4) 0.000(4) 0.003(3) C29 0.051(5) 0.054(4) 0.047(4) 0.016(4) 0.003(4) 0.011(4) C30 0.054(5) 0.042(4) 0.045(4) -0.003(3) -0.002(4) 0.011(4) Cl1 0.0960(16) 0.1147(16) 0.0500(11) -0.0215(11) 0.0103(11) -0.0169(12) Cl2 0.1063(18) 0.0629(12) 0.0995(15) -0.0300(11) 0.0212(13) 0.0020(11) Cl3 0.1115(17) 0.0604(11) 0.0719(13) -0.0165(10) 0.0020(12) 0.0129(11) Cl4 0.0969(16) 0.0420(10) 0.0919(14) 0.0128(10) 0.0016(12) 0.0152(10) N1 0.068(4) 0.033(3) 0.044(3) -0.009(3) 0.007(3) 0.010(3) N2 0.089(5) 0.065(4) 0.087(5) 0.022(3) 0.002(4) 0.018(4) N3 0.054(4) 0.037(3) 0.050(4) 0.000(3) 0.001(3) -0.003(3) N4 0.055(4) 0.044(3) 0.046(3) -0.011(3) 0.005(3) 0.003(3) N5 0.050(4) 0.043(3) 0.052(4) 0.013(3) -0.002(3) 0.013(3) N6 0.117(6) 0.085(5) 0.072(5) -0.011(4) 0.009(5) 0.037(4) N7 0.055(4) 0.037(3) 0.048(3) 0.004(3) 0.004(3) 0.003(3) N8 0.062(4) 0.039(3) 0.047(3) 0.002(3) -0.001(3) -0.001(3) O1 0.106(4) 0.040(3) 0.049(3) 0.000(2) 0.001(3) 0.018(3) O2 0.095(4) 0.054(3) 0.047(3) -0.003(2) 0.003(3) 0.008(2) O3 0.083(4) 0.050(3) 0.050(3) -0.001(2) -0.007(3) 0.016(2) O4 0.082(4) 0.049(3) 0.079(3) 0.007(3) 0.005(3) 0.028(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N3 1.316(6) . ? C1 C5 1.438(6) . ? C1 C2 1.470(7) . ? C2 O1 1.233(5) . ? C2 N1 1.381(6) . ? C3 O2 1.223(5) . ? C3 N1 1.386(6) . ? C3 C4 1.458(7) . ? C4 C5 1.341(6) . ? C4 C8 1.430(7) . ? C5 C9 1.506(6) . ? C6 N1 1.476(6) . ? C6 C7 1.552(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N2 1.140(6) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.376(7) . ? C10 C15 1.393(6) . ? C10 N4 1.409(6) . ? C11 C12 1.405(7) . ? C11 H11 0.9300 . ? C12 C13 1.372(7) . ? C12 Cl2 1.728(5) . ? C13 C14 1.353(7) . ? C13 Cl1 1.735(5) . ? C14 C15 1.420(7) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 N7 1.340(6) . ? C16 C20 1.433(7) . ? C16 C17 1.438(7) . ? C17 O3 1.233(6) . ? C17 N5 1.392(6) . ? C18 O4 1.214(6) . ? C18 N5 1.400(7) . ? C18 C19 1.475(7) . ? C19 C20 1.360(6) . ? C19 C23 1.431(7) . ? C20 C24 1.515(6) . ? C21 N5 1.479(6) . ? C21 C22 1.491(7) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 N6 1.130(7) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.374(6) . ? C25 C30 1.382(6) . ? C25 N8 1.430(5) . ? C26 C27 1.378(6) . ? C26 H26 0.9300 . ? C27 C28 1.368(6) . ? C27 Cl3 1.715(6) . ? C28 C29 1.374(7) . ? C28 Cl4 1.722(5) . ? C29 C30 1.381(6) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? N3 N4 1.318(5) . ? N4 H4 0.8600 . ? N7 N8 1.298(5) . ? N8 H8 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 N3 C1 C5 116.5(5) . . ? N3 C1 C2 123.7(5) . . ? C5 C1 C2 119.8(5) . . ? O1 C2 N1 120.7(5) . . ? O1 C2 C1 121.3(6) . . ? N1 C2 C1 118.0(5) . . ? O2 C3 N1 119.9(6) . . ? O2 C3 C4 123.2(6) . . ? N1 C3 C4 116.9(5) . . ? C5 C4 C8 121.0(6) . . ? C5 C4 C3 123.7(5) . . ? C8 C4 C3 115.3(5) . . ? C4 C5 C1 118.3(5) . . ? C4 C5 C9 121.7(5) . . ? C1 C5 C9 120.0(5) . . ? N1 C6 C7 110.0(5) . . ? N1 C6 H6A 109.7 . . ? C7 C6 H6A 109.7 . . ? N1 C6 H6B 109.7 . . ? C7 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 C4 178.2(7) . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 121.8(6) . . ? C11 C10 N4 120.3(6) . . ? C15 C10 N4 117.8(6) . . ? C10 C11 C12 117.0(6) . . ? C10 C11 H11 121.5 . . ? C12 C11 H11 121.5 . . ? C13 C12 C11 120.9(5) . . ? C13 C12 Cl2 122.3(5) . . ? C11 C12 Cl2 116.8(5) . . ? C14 C13 C12 122.9(6) . . ? C14 C13 Cl1 117.4(5) . . ? C12 C13 Cl1 119.7(5) . . ? C13 C14 C15 117.2(6) . . ? C13 C14 H14 121.4 . . ? C15 C14 H14 121.4 . . ? C10 C15 C14 120.0(6) . . ? C10 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? N7 C16 C20 114.5(5) . . ? N7 C16 C17 123.9(6) . . ? C20 C16 C17 121.5(6) . . ? O3 C17 N5 119.8(6) . . ? O3 C17 C16 122.9(6) . . ? N5 C17 C16 117.3(6) . . ? O4 C18 N5 121.6(6) . . ? O4 C18 C19 121.2(6) . . ? N5 C18 C19 117.0(6) . . ? C20 C19 C23 122.0(6) . . ? C20 C19 C18 121.6(6) . . ? C23 C19 C18 116.3(6) . . ? C19 C20 C16 118.9(5) . . ? C19 C20 C24 121.0(6) . . ? C16 C20 C24 120.1(5) . . ? N5 C21 C22 112.7(5) . . ? N5 C21 H21A 109.1 . . ? C22 C21 H21A 109.1 . . ? N5 C21 H21B 109.1 . . ? C22 C21 H21B 109.1 . . ? H21A C21 H21B 107.8 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N6 C23 C19 175.9(7) . . ? C20 C24 H24A 109.5 . . ? C20 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C20 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C30 121.8(5) . . ? C26 C25 N8 118.3(5) . . ? C30 C25 N8 119.9(6) . . ? C25 C26 C27 118.9(5) . . ? C25 C26 H26 120.6 . . ? C27 C26 H26 120.6 . . ? C28 C27 C26 120.4(6) . . ? C28 C27 Cl3 121.5(5) . . ? C26 C27 Cl3 118.1(5) . . ? C27 C28 C29 120.1(5) . . ? C27 C28 Cl4 120.7(5) . . ? C29 C28 Cl4 119.2(5) . . ? C28 C29 C30 120.8(5) . . ? C28 C29 H29 119.6 . . ? C30 C29 H29 119.6 . . ? C29 C30 C25 118.0(5) . . ? C29 C30 H30 121.0 . . ? C25 C30 H30 121.0 . . ? C2 N1 C3 123.2(5) . . ? C2 N1 C6 116.4(5) . . ? C3 N1 C6 120.4(5) . . ? C1 N3 N4 120.4(5) . . ? N3 N4 C10 121.5(5) . . ? N3 N4 H4 119.2 . . ? C10 N4 H4 119.2 . . ? C17 N5 C18 123.5(5) . . ? C17 N5 C21 118.0(5) . . ? C18 N5 C21 118.5(5) . . ? N8 N7 C16 120.9(5) . . ? N7 N8 C25 119.4(5) . . ? N7 N8 H8 120.3 . . ? C25 N8 H8 120.3 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.437 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.058 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 760910' #TrackingRef '- 1-5-OK.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl2 N4 O2' _chemical_formula_sum 'C14 H10 Cl2 N4 O2' _chemical_formula_weight 337.16 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 8.5409(12) _cell_length_b 11.9685(16) _cell_length_c 14.529(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.756(2) _cell_angle_gamma 90.00 _cell_volume 1448.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1082 _cell_measurement_theta_min 2.278 _cell_measurement_theta_max 21.534 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.460 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9300 _exptl_absorpt_correction_T_max 0.9534 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7116 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0696 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2539 _reflns_number_gt 1337 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (BRUKER 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0999P)^2^] 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 2539 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1110 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.1877 _refine_ls_wR_factor_gt 0.1722 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 0.934 _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 0.3354(5) 0.6525(3) 0.9068(3) 0.0431(10) Uani 1 1 d . . . C2 C 0.3982(5) 0.6049(4) 0.8295(3) 0.0448(11) Uani 1 1 d . . . C3 C 0.4314(5) 0.7928(4) 0.7717(3) 0.0551(12) Uani 1 1 d . . . C4 C 0.3805(5) 0.8377(3) 0.8544(3) 0.0484(11) Uani 1 1 d . . . C5 C 0.3315(5) 0.7716(3) 0.9187(3) 0.0458(11) Uani 1 1 d . . . C6 C 0.5046(6) 0.6310(4) 0.6887(3) 0.0647(14) Uani 1 1 d . . . H6A H 0.5621 0.5633 0.7091 0.097 Uiso 1 1 calc R . . H6B H 0.5756 0.6839 0.6694 0.097 Uiso 1 1 calc R . . H6C H 0.4169 0.6151 0.6364 0.097 Uiso 1 1 calc R . . C7 C 0.3815(5) 0.9574(4) 0.8622(3) 0.0565(13) Uani 1 1 d . . . C8 C 0.2691(6) 0.8191(4) 0.9992(3) 0.0602(13) Uani 1 1 d . . . H8A H 0.3576 0.8373 1.0503 0.090 Uiso 1 1 calc R . . H8B H 0.2016 0.7650 1.0202 0.090 Uiso 1 1 calc R . . H8C H 0.2081 0.8854 0.9787 0.090 Uiso 1 1 calc R . . C9 C 0.2219(5) 0.4190(4) 1.0303(3) 0.0469(11) Uani 1 1 d . . . C10 C 0.2339(5) 0.3060(4) 1.0233(3) 0.0513(12) Uani 1 1 d . . . H10 H 0.2779 0.2740 0.9764 0.062 Uiso 1 1 calc R . . C11 C 0.1775(5) 0.2383(3) 1.0893(3) 0.0494(12) Uani 1 1 d . . . C12 C 0.1159(5) 0.2884(4) 1.1591(3) 0.0536(12) Uani 1 1 d . . . C13 C 0.1043(6) 0.3996(4) 1.1654(3) 0.0583(13) Uani 1 1 d . . . H13 H 0.0617 0.4312 1.2130 0.070 Uiso 1 1 calc R . . C14 C 0.1561(5) 0.4676(4) 1.1005(3) 0.0548(12) Uani 1 1 d . . . H14 H 0.1470 0.5448 1.1038 0.066 Uiso 1 1 calc R . . Cl1 Cl 0.19264(17) 0.09542(10) 1.07928(9) 0.0734(5) Uani 1 1 d . . . Cl2 Cl 0.04973(17) 0.20257(11) 1.23998(9) 0.0735(5) Uani 1 1 d . . . N1 N 0.4423(4) 0.6778(3) 0.7664(2) 0.0478(9) Uani 1 1 d . . . N2 N 0.3840(5) 1.0527(4) 0.8703(3) 0.0782(14) Uani 1 1 d . . . N3 N 0.2834(4) 0.5916(3) 0.9697(2) 0.0453(9) Uani 1 1 d . . . N4 N 0.2809(4) 0.4838(3) 0.9641(2) 0.0490(10) Uani 1 1 d . . . H4 H 0.3155 0.4512 0.9197 0.059 Uiso 1 1 calc R . . O1 O 0.4106(4) 0.5030(3) 0.8208(2) 0.0602(9) Uani 1 1 d . . . O2 O 0.4636(4) 0.8524(3) 0.7100(2) 0.0768(11) 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 0.046(3) 0.040(2) 0.043(2) -0.0047(19) 0.010(2) 0.000(2) C2 0.045(3) 0.049(3) 0.041(2) -0.002(2) 0.011(2) -0.004(2) C3 0.055(3) 0.060(3) 0.051(3) 0.002(2) 0.013(2) -0.003(2) C4 0.052(3) 0.038(3) 0.054(3) 0.004(2) 0.011(2) -0.004(2) C5 0.045(3) 0.041(3) 0.050(3) 0.000(2) 0.009(2) -0.002(2) C6 0.079(4) 0.070(3) 0.051(3) 0.005(3) 0.028(3) 0.002(3) C7 0.053(3) 0.055(3) 0.060(3) 0.005(3) 0.011(2) -0.002(3) C8 0.075(3) 0.054(3) 0.057(3) -0.015(2) 0.027(3) -0.005(2) C9 0.050(3) 0.046(3) 0.044(3) 0.002(2) 0.008(2) -0.001(2) C10 0.056(3) 0.049(3) 0.049(3) -0.001(2) 0.012(2) -0.003(2) C11 0.050(3) 0.035(2) 0.059(3) 0.000(2) 0.005(2) -0.005(2) C12 0.055(3) 0.059(3) 0.048(3) 0.000(2) 0.013(2) -0.006(2) C13 0.063(3) 0.049(3) 0.064(3) 0.001(2) 0.016(2) -0.003(2) C14 0.063(3) 0.043(3) 0.059(3) -0.002(2) 0.015(2) -0.005(2) Cl1 0.0987(11) 0.0442(8) 0.0838(10) 0.0011(6) 0.0338(8) -0.0007(7) Cl2 0.0891(10) 0.0716(10) 0.0653(9) 0.0139(7) 0.0292(7) -0.0125(7) N1 0.052(2) 0.048(2) 0.044(2) 0.0031(17) 0.0142(17) 0.0013(18) N2 0.083(3) 0.043(3) 0.106(4) 0.007(2) 0.016(3) -0.007(2) N3 0.050(2) 0.039(2) 0.047(2) -0.0001(17) 0.0122(17) -0.0049(17) N4 0.059(2) 0.043(2) 0.047(2) 0.0015(17) 0.0180(18) 0.0007(18) O1 0.080(2) 0.045(2) 0.062(2) -0.0038(16) 0.0289(17) 0.0026(17) O2 0.113(3) 0.061(2) 0.064(2) 0.0135(18) 0.035(2) -0.008(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 N3 1.320(5) . ? C1 C5 1.438(6) . ? C1 C2 1.463(6) . ? C2 O1 1.233(5) . ? C2 N1 1.376(5) . ? C3 O2 1.223(5) . ? C3 N1 1.383(5) . ? C3 C4 1.467(6) . ? C4 C5 1.359(6) . ? C4 C7 1.437(6) . ? C5 C8 1.500(6) . ? C6 N1 1.463(5) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N2 1.146(6) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.363(5) . ? C9 C14 1.395(6) . ? C9 N4 1.412(5) . ? C10 C11 1.418(6) . ? C10 H10 0.9300 . ? C11 C12 1.379(6) . ? C11 Cl1 1.723(4) . ? C12 C13 1.339(6) . ? C12 Cl2 1.746(5) . ? C13 C14 1.390(6) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? N3 N4 1.294(4) . ? N4 H4 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 N3 C1 C5 116.3(4) . . ? N3 C1 C2 123.6(4) . . ? C5 C1 C2 120.1(4) . . ? O1 C2 N1 121.1(4) . . ? O1 C2 C1 121.2(4) . . ? N1 C2 C1 117.7(4) . . ? O2 C3 N1 120.7(5) . . ? O2 C3 C4 122.8(4) . . ? N1 C3 C4 116.5(4) . . ? C5 C4 C7 121.6(4) . . ? C5 C4 C3 122.8(4) . . ? C7 C4 C3 115.6(4) . . ? C4 C5 C1 118.4(4) . . ? C4 C5 C8 122.1(4) . . ? C1 C5 C8 119.4(4) . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 C4 178.6(5) . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 121.2(4) . . ? C10 C9 N4 116.7(4) . . ? C14 C9 N4 122.1(4) . . ? C9 C10 C11 118.3(4) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? C12 C11 C10 119.4(4) . . ? C12 C11 Cl1 122.8(4) . . ? C10 C11 Cl1 117.8(4) . . ? C13 C12 C11 121.9(4) . . ? C13 C12 Cl2 119.9(4) . . ? C11 C12 Cl2 118.1(4) . . ? C12 C13 C14 119.7(5) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C13 C14 C9 119.5(4) . . ? C13 C14 H14 120.3 . . ? C9 C14 H14 120.3 . . ? C2 N1 C3 124.2(4) . . ? C2 N1 C6 118.1(4) . . ? C3 N1 C6 117.7(4) . . ? N4 N3 C1 120.7(4) . . ? N3 N4 C9 120.5(4) . . ? N3 N4 H4 119.7 . . ? C9 N4 H4 119.7 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.905 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.064 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 760911' #TrackingRef '- 1-5-OK.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H30 Cl4 N8 Ni O6, H4 O2' _chemical_formula_sum 'C32 H34 Cl4 N8 Ni O8' _chemical_formula_weight 859.18 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Ccc2 _symmetry_space_group_name_Hall 'C 2 -2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x, -y, z+1/2' '-x, y, z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 21.943(3) _cell_length_b 24.179(4) _cell_length_c 7.5298(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3995.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 7747 _cell_measurement_theta_min 2.507 _cell_measurement_theta_max 28.157 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1768 _exptl_absorpt_coefficient_mu 0.810 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8951 _exptl_absorpt_correction_T_max 0.9234 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9374 _diffrn_reflns_av_R_equivalents 0.0778 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3395 _reflns_number_gt 3236 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (BRUKER 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0452P)^2^+99.3960P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(1) _refine_ls_number_reflns 3395 _refine_ls_number_parameters 225 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0978 _refine_ls_R_factor_gt 0.0923 _refine_ls_wR_factor_ref 0.1931 _refine_ls_wR_factor_gt 0.1902 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.083 _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 Ni1 Ni 0.7500 0.7500 0.7643(3) 0.0321(4) Uani 1 2 d S . . C1 C 0.8904(4) 0.7168(5) 0.8657(15) 0.0338(17) Uani 1 1 d . . . C2 C 0.8797(4) 0.7684(4) 0.7835(15) 0.0304(17) Uani 1 1 d . . . C3 C 0.9909(4) 0.7814(4) 0.7554(18) 0.0338(17) Uani 1 1 d . . . C4 C 0.9985(5) 0.7294(5) 0.8356(14) 0.030(2) Uani 1 1 d . . . C5 C 0.9520(5) 0.6954(5) 0.8902(14) 0.0304(17) Uani 1 1 d . . . C6 C 0.9214(6) 0.8527(6) 0.648(2) 0.062(4) Uani 1 1 d . . . H6A H 0.8823 0.8531 0.5876 0.075 Uiso 1 1 calc R . . H6B H 0.9526 0.8588 0.5583 0.075 Uiso 1 1 calc R . . C7 C 0.9231(10) 0.8980(7) 0.772(3) 0.108(7) Uani 1 1 d . . . H7A H 0.9511 0.8894 0.8663 0.161 Uiso 1 1 calc R . . H7B H 0.8831 0.9036 0.8212 0.161 Uiso 1 1 calc R . . H7C H 0.9361 0.9310 0.7126 0.161 Uiso 1 1 calc R . . C8 C 1.0612(5) 0.7130(6) 0.863(2) 0.054(4) Uani 1 1 d . . . C9 C 0.9623(6) 0.6401(5) 0.967(2) 0.052(4) Uani 1 1 d . . . H9A H 1.0033 0.6378 1.0113 0.078 Uiso 1 1 calc R . . H9B H 0.9561 0.6124 0.8778 0.078 Uiso 1 1 calc R . . H9C H 0.9342 0.6342 1.0633 0.078 Uiso 1 1 calc R . . C10 C 0.7582(5) 0.6574(5) 1.0354(16) 0.038(2) Uani 1 1 d . . . C11 C 0.7693(5) 0.6002(5) 1.0420(16) 0.038(2) Uani 1 1 d . . . H11 H 0.8033 0.5860 0.9845 0.045 Uiso 1 1 calc R . . C12 C 0.7316(6) 0.5653(6) 1.130(2) 0.056(4) Uani 1 1 d . . . C13 C 0.6782(6) 0.5859(6) 1.2126(16) 0.052(4) Uani 1 1 d . . . C14 C 0.6663(6) 0.6378(5) 1.2003(16) 0.045(3) Uani 1 1 d . . . H14 H 0.6310 0.6509 1.2537 0.055 Uiso 1 1 calc R . . C15 C 0.7027(5) 0.6747(5) 1.1132(16) 0.034(3) Uani 1 1 d . . . H15 H 0.6908 0.7116 1.1049 0.041 Uiso 1 1 calc R . . C16 C 0.7718(9) 0.6408(7) 0.558(3) 0.090(5) Uani 1 1 d DU . . H16A H 0.8118 0.6249 0.5570 0.135 Uiso 1 1 calc R . . H16B H 0.7497 0.6288 0.4553 0.135 Uiso 1 1 calc R . . H16C H 0.7506 0.6293 0.6635 0.135 Uiso 1 1 calc R . . Cl1 Cl 0.7548(3) 0.4965(2) 1.1430(8) 0.1038(18) Uani 1 1 d . . . Cl2 Cl 0.6307(2) 0.5382(2) 1.3151(8) 0.1026(19) Uani 1 1 d . . . N1 N 0.9305(4) 0.7989(4) 0.7246(12) 0.034(2) Uani 1 1 d . . . N2 N 1.1097(5) 0.7022(7) 0.884(2) 0.085(5) Uani 1 1 d . . . N3 N 0.8475(4) 0.6833(4) 0.9434(13) 0.032(2) Uani 1 1 d . . . N4 N 0.7911(4) 0.6962(4) 0.9412(12) 0.034(2) Uani 1 1 d . . . O1 O 0.8299(3) 0.7871(3) 0.7447(13) 0.0359(19) Uani 1 1 d . . . O2 O 1.0323(4) 0.8110(5) 0.7050(14) 0.069(3) Uani 1 1 d . . . O3 O 0.7763(4) 0.6962(4) 0.5566(14) 0.051(2) Uani 1 1 d DU . . H3A H 0.8140 0.7025 0.5403 0.077 Uiso 1 1 d R . . O4 O 0.9493(18) 0.5021(15) 0.166(16) 0.73(8) Uani 1 1 d . . . H4A H 0.9507 0.4673 0.1501 1.088 Uiso 1 1 d R . . H4B H 0.9864 0.5064 0.1364 1.088 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 Ni1 0.0168(7) 0.0424(10) 0.0372(10) 0.000 0.000 -0.0048(8) C1 0.019(3) 0.054(5) 0.028(4) 0.005(4) -0.010(3) -0.002(3) C2 0.033(4) 0.044(4) 0.014(4) -0.013(3) -0.005(3) -0.001(3) C3 0.019(3) 0.054(5) 0.028(4) 0.005(4) -0.010(3) -0.002(3) C4 0.023(5) 0.051(6) 0.018(5) -0.023(5) -0.006(4) 0.005(5) C5 0.033(4) 0.044(4) 0.014(4) -0.013(3) -0.005(3) -0.001(3) C6 0.036(7) 0.061(9) 0.090(12) 0.002(9) 0.002(7) -0.033(7) C7 0.17(2) 0.062(10) 0.088(13) 0.000(13) -0.015(18) 0.023(12) C8 0.021(6) 0.067(9) 0.072(10) -0.016(8) 0.000(6) 0.010(6) C9 0.039(7) 0.039(7) 0.077(10) -0.006(7) -0.009(7) 0.024(6) C10 0.021(4) 0.052(5) 0.040(5) 0.002(4) 0.002(3) 0.013(3) C11 0.021(4) 0.052(5) 0.040(5) 0.002(4) 0.002(3) 0.013(3) C12 0.060(8) 0.062(9) 0.047(8) 0.009(7) 0.003(7) -0.008(7) C13 0.047(7) 0.071(9) 0.038(8) 0.010(6) 0.011(6) -0.015(7) C14 0.043(7) 0.056(8) 0.037(7) 0.023(6) 0.014(5) 0.024(6) C15 0.023(5) 0.032(6) 0.049(8) 0.008(5) -0.004(5) 0.010(5) C16 0.076(10) 0.107(11) 0.087(11) -0.011(10) 0.003(9) -0.008(10) Cl1 0.144(5) 0.051(2) 0.117(4) 0.009(3) 0.032(4) 0.005(3) Cl2 0.101(3) 0.092(3) 0.115(5) 0.025(3) 0.032(3) -0.045(3) N1 0.025(4) 0.047(5) 0.029(6) -0.001(4) 0.000(4) -0.006(4) N2 0.028(6) 0.136(13) 0.090(11) -0.016(10) 0.003(6) 0.023(7) N3 0.021(4) 0.031(5) 0.046(6) -0.001(4) -0.001(4) 0.000(4) N4 0.027(5) 0.046(6) 0.029(6) 0.019(5) 0.008(4) 0.010(4) O1 0.011(3) 0.038(4) 0.059(6) 0.016(4) -0.011(4) -0.001(3) O2 0.022(4) 0.093(8) 0.093(10) 0.009(6) 0.002(4) -0.019(5) O3 0.032(4) 0.051(5) 0.070(6) -0.014(5) 0.014(4) -0.019(4) O4 0.66(9) 0.063(11) 1.4(2) 0.13(5) -0.43(14) -0.08(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 Ni1 O1 1.976(6) . ? Ni1 O1 1.976(6) 6_665 ? Ni1 N4 2.069(9) 6_665 ? Ni1 N4 2.069(9) . ? Ni1 O3 2.115(10) 6_665 ? Ni1 O3 2.115(10) . ? C1 N3 1.372(14) . ? C1 C2 1.413(15) . ? C1 C5 1.461(14) . ? C2 O1 1.219(11) . ? C2 N1 1.406(13) . ? C3 O2 1.217(13) . ? C3 C4 1.405(15) . ? C3 N1 1.410(12) . ? C4 C5 1.373(16) . ? C4 C8 1.446(15) . ? C5 C9 1.474(17) . ? C6 N1 1.439(18) . ? C6 C7 1.44(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N2 1.107(16) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 N4 1.381(15) . ? C10 C11 1.404(17) . ? C10 C15 1.415(15) . ? C11 C12 1.355(18) . ? C11 H11 0.9300 . ? C12 C13 1.416(19) . ? C12 Cl1 1.743(16) . ? C13 C14 1.285(19) . ? C13 Cl2 1.736(13) . ? C14 C15 1.365(16) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 O3 1.341(15) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? N3 N4 1.275(12) . ? O3 H3A 0.8500 . ? O4 H4A 0.8500 . ? O4 H4B 0.8498 . ? 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 Ni1 O1 171.4(6) . 6_665 ? O1 Ni1 N4 98.6(4) . 6_665 ? O1 Ni1 N4 87.0(3) 6_665 6_665 ? O1 Ni1 N4 87.0(3) . . ? O1 Ni1 N4 98.6(4) 6_665 . ? N4 Ni1 N4 99.9(6) 6_665 . ? O1 Ni1 O3 84.6(3) . 6_665 ? O1 Ni1 O3 89.0(4) 6_665 6_665 ? N4 Ni1 O3 88.3(4) 6_665 6_665 ? N4 Ni1 O3 169.1(4) . 6_665 ? O1 Ni1 O3 89.0(4) . . ? O1 Ni1 O3 84.6(3) 6_665 . ? N4 Ni1 O3 169.1(4) 6_665 . ? N4 Ni1 O3 88.3(4) . . ? O3 Ni1 O3 84.6(6) 6_665 . ? N3 C1 C2 126.5(9) . . ? N3 C1 C5 111.8(9) . . ? C2 C1 C5 121.5(10) . . ? O1 C2 N1 116.1(10) . . ? O1 C2 C1 125.5(10) . . ? N1 C2 C1 118.0(9) . . ? O2 C3 C4 124.7(10) . . ? O2 C3 N1 118.4(10) . . ? C4 C3 N1 116.8(9) . . ? C5 C4 C3 125.2(10) . . ? C5 C4 C8 119.9(12) . . ? C3 C4 C8 114.9(11) . . ? C4 C5 C1 115.9(10) . . ? C4 C5 C9 123.2(11) . . ? C1 C5 C9 120.9(10) . . ? N1 C6 C7 114.8(15) . . ? N1 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? N1 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.5 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 C4 177.7(18) . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N4 C10 C11 126.6(10) . . ? N4 C10 C15 117.5(10) . . ? C11 C10 C15 115.2(11) . . ? C12 C11 C10 121.7(11) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C11 C12 C13 120.0(13) . . ? C11 C12 Cl1 116.4(11) . . ? C13 C12 Cl1 123.6(11) . . ? C14 C13 C12 118.7(12) . . ? C14 C13 Cl2 123.9(11) . . ? C12 C13 Cl2 117.3(11) . . ? C13 C14 C15 123.7(11) . . ? C13 C14 H14 118.1 . . ? C15 C14 H14 118.1 . . ? C14 C15 C10 120.5(11) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C2 N1 C3 122.4(9) . . ? C2 N1 C6 119.4(9) . . ? C3 N1 C6 117.8(9) . . ? N4 N3 C1 121.1(9) . . ? N3 N4 C10 109.6(9) . . ? N3 N4 Ni1 125.8(7) . . ? C10 N4 Ni1 122.0(7) . . ? C2 O1 Ni1 127.6(7) . . ? C16 O3 Ni1 126.0(11) . . ? C16 O3 H3A 104.5 . . ? Ni1 O3 H3A 105.2 . . ? H4A O4 H4B 92.9 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.977 _refine_diff_density_min -0.797 _refine_diff_density_rms 0.126 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 760912' #TrackingRef '- 1-5-OK.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H22 Cl4 Cu N8 O4' _chemical_formula_sum 'C30 H22 Cl4 Cu N8 O4' _chemical_formula_weight 763.91 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' 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' 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' _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 7.642(7) _cell_length_b 8.378(8) _cell_length_c 13.350(12) _cell_angle_alpha 72.398(15) _cell_angle_beta 87.327(15) _cell_angle_gamma 72.126(13) _cell_volume 774.4(12) _cell_formula_units_Z 1 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 945 _cell_measurement_theta_min 2.805 _cell_measurement_theta_max 22.713 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.638 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 387 _exptl_absorpt_coefficient_mu 1.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8977 _exptl_absorpt_correction_T_max 0.8977 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3838 _diffrn_reflns_av_R_equivalents 0.0890 _diffrn_reflns_av_sigmaI/netI 0.1089 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2661 _reflns_number_gt 1660 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (BRUKER 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1160P)^2^+3.9600P] 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 2661 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1217 _refine_ls_R_factor_gt 0.0775 _refine_ls_wR_factor_ref 0.2541 _refine_ls_wR_factor_gt 0.1955 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.5000 0.5000 0.0382(5) Uani 1 2 d S . . C1 C 0.6797(9) 0.1008(9) 0.4875(7) 0.040(2) Uani 1 1 d . . . C2 C 0.6649(9) 0.1289(9) 0.5896(6) 0.0308(17) Uani 1 1 d . . . C3 C 0.8953(10) -0.1623(10) 0.6674(7) 0.041(2) Uani 1 1 d . . . C4 C 0.9049(9) -0.1805(9) 0.5617(7) 0.0342(18) Uani 1 1 d . . . C5 C 0.7990(9) -0.0605(9) 0.4740(7) 0.0348(18) Uani 1 1 d . . . C6 C 0.7390(12) 0.0110(10) 0.7837(7) 0.046(2) Uani 1 1 d . . . H6A H 0.6772 0.1333 0.7785 0.055 Uiso 1 1 calc R . . H6B H 0.8597 -0.0224 0.8180 0.055 Uiso 1 1 calc R . . C7 C 0.6299(18) -0.1012(17) 0.8501(9) 0.083(4) Uani 1 1 d . . . H7A H 0.5043 -0.0558 0.8231 0.124 Uiso 1 1 calc R . . H7B H 0.6346 -0.0992 0.9214 0.124 Uiso 1 1 calc R . . H7C H 0.6815 -0.2200 0.8480 0.124 Uiso 1 1 calc R . . C8 C 1.0484(10) -0.3322(10) 0.5506(7) 0.040(2) Uani 1 1 d . . . C9 C 0.8102(11) -0.0887(10) 0.3694(7) 0.045(2) Uani 1 1 d . . . H9A H 0.9240 -0.1769 0.3667 0.067 Uiso 1 1 calc R . . H9B H 0.8051 0.0194 0.3159 0.067 Uiso 1 1 calc R . . H9C H 0.7089 -0.1270 0.3576 0.067 Uiso 1 1 calc R . . C10 C 0.4136(10) 0.4759(9) 0.2891(7) 0.0378(19) Uani 1 1 d . . . C11 C 0.2240(10) 0.5474(9) 0.2713(7) 0.042(2) Uani 1 1 d . . . H11 H 0.1473 0.5351 0.3273 0.050 Uiso 1 1 calc R . . C12 C 0.1494(11) 0.6372(10) 0.1697(8) 0.048(2) Uani 1 1 d . . . C13 C 0.2631(13) 0.6593(12) 0.0873(6) 0.049(2) Uani 1 1 d . . . C14 C 0.4524(12) 0.5917(12) 0.1045(8) 0.055(2) Uani 1 1 d . . . H14 H 0.5286 0.6088 0.0485 0.066 Uiso 1 1 calc R . . C15 C 0.5277(11) 0.4994(11) 0.2047(7) 0.044(2) Uani 1 1 d . . . H15 H 0.6548 0.4526 0.2163 0.053 Uiso 1 1 calc R . . Cl1 Cl 0.1737(5) 0.7676(5) -0.0410(2) 0.1042(13) Uani 1 1 d . . . Cl2 Cl -0.0863(3) 0.7203(3) 0.1502(2) 0.0709(8) Uani 1 1 d . . . N1 N 0.7614(8) -0.0076(8) 0.6752(6) 0.0393(16) Uani 1 1 d . . . N2 N 1.1663(9) -0.4491(9) 0.5421(7) 0.053(2) Uani 1 1 d . . . N3 N 0.5843(8) 0.2199(7) 0.3994(6) 0.0384(16) Uani 1 1 d . . . N4 N 0.4914(8) 0.3793(8) 0.3950(5) 0.0350(15) Uani 1 1 d . . . O1 O 0.5657(7) 0.2690(6) 0.6065(4) 0.0375(13) Uani 1 1 d . . . O2 O 0.9919(8) -0.2649(7) 0.7405(5) 0.0550(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0310(7) 0.0213(7) 0.0528(9) -0.0090(6) -0.0040(6) 0.0042(5) C1 0.018(3) 0.018(4) 0.080(6) -0.017(4) -0.007(4) 0.003(3) C2 0.021(3) 0.022(4) 0.050(5) -0.015(3) -0.003(3) -0.003(3) C3 0.030(4) 0.026(4) 0.064(6) -0.012(4) -0.002(4) -0.003(3) C4 0.024(3) 0.017(3) 0.057(5) -0.010(3) -0.005(3) 0.002(3) C5 0.023(3) 0.029(4) 0.055(5) -0.017(4) 0.003(3) -0.008(3) C6 0.050(5) 0.029(4) 0.048(5) -0.012(4) -0.012(4) 0.006(4) C7 0.102(9) 0.100(9) 0.053(7) -0.016(7) 0.026(6) -0.050(8) C8 0.025(4) 0.026(4) 0.072(6) -0.019(4) 0.000(4) -0.005(3) C9 0.037(4) 0.031(4) 0.060(6) -0.015(4) 0.003(4) -0.002(3) C10 0.030(4) 0.023(4) 0.053(5) -0.007(3) -0.014(4) 0.001(3) C11 0.029(4) 0.022(4) 0.069(6) -0.011(4) -0.007(4) 0.000(3) C12 0.033(4) 0.030(4) 0.073(7) -0.015(4) -0.014(4) 0.005(3) C13 0.056(5) 0.052(5) 0.026(4) -0.011(4) -0.013(4) 0.006(4) C14 0.051(5) 0.050(5) 0.053(6) -0.013(5) 0.004(5) -0.001(4) C15 0.033(4) 0.043(5) 0.044(5) -0.010(4) -0.005(4) 0.004(4) Cl1 0.083(2) 0.114(3) 0.0592(18) -0.0018(18) -0.0164(16) 0.0281(19) Cl2 0.0369(12) 0.0685(16) 0.0854(19) -0.0114(14) -0.0235(12) 0.0065(11) N1 0.028(3) 0.025(3) 0.058(5) -0.011(3) -0.006(3) 0.001(3) N2 0.027(3) 0.031(4) 0.096(7) -0.021(4) -0.001(4) 0.000(3) N3 0.020(3) 0.023(3) 0.067(5) -0.010(3) -0.002(3) -0.003(3) N4 0.026(3) 0.027(3) 0.049(4) -0.014(3) -0.008(3) 0.001(3) O1 0.034(3) 0.024(3) 0.044(3) -0.007(2) 0.001(2) 0.003(2) O2 0.044(3) 0.027(3) 0.073(4) -0.003(3) -0.022(3) 0.012(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.956(5) 2_666 ? Cu1 O1 1.956(5) . ? Cu1 N4 1.975(6) 2_666 ? Cu1 N4 1.975(6) . ? Cu1 N2 2.519(7) 1_465 ? Cu1 N2 2.519(7) 2_756 ? C1 N3 1.354(10) . ? C1 C5 1.437(10) . ? C1 C2 1.446(12) . ? C2 O1 1.265(8) . ? C2 N1 1.389(10) . ? C3 O2 1.186(10) . ? C3 N1 1.413(10) . ? C3 C4 1.460(12) . ? C4 C5 1.384(11) . ? C4 C8 1.443(10) . ? C5 C9 1.480(12) . ? C6 N1 1.499(11) . ? C6 C7 1.507(13) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N2 1.140(9) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.388(10) . ? C10 C15 1.395(12) . ? C10 N4 1.449(10) . ? C11 C12 1.386(12) . ? C11 H11 0.9300 . ? C12 C13 1.372(13) . ? C12 Cl2 1.721(8) . ? C13 C14 1.385(12) . ? C13 Cl1 1.736(8) . ? C14 C15 1.375(12) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? N2 Cu1 2.519(7) 1_645 ? N3 N4 1.291(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 180.0(3) 2_666 . ? O1 Cu1 N4 87.6(3) 2_666 2_666 ? O1 Cu1 N4 92.4(3) . 2_666 ? O1 Cu1 N4 92.4(3) 2_666 . ? O1 Cu1 N4 87.6(3) . . ? N4 Cu1 N4 180.000(1) 2_666 . ? O1 Cu1 N2 89.7(2) 2_666 1_465 ? O1 Cu1 N2 90.3(2) . 1_465 ? N4 Cu1 N2 84.8(3) 2_666 1_465 ? N4 Cu1 N2 95.2(3) . 1_465 ? O1 Cu1 N2 90.3(2) 2_666 2_756 ? O1 Cu1 N2 89.7(2) . 2_756 ? N4 Cu1 N2 95.2(3) 2_666 2_756 ? N4 Cu1 N2 84.8(3) . 2_756 ? N2 Cu1 N2 180.0 1_465 2_756 ? N3 C1 C5 115.5(8) . . ? N3 C1 C2 123.7(6) . . ? C5 C1 C2 120.8(7) . . ? O1 C2 N1 117.7(7) . . ? O1 C2 C1 124.0(7) . . ? N1 C2 C1 118.2(6) . . ? O2 C3 N1 122.1(9) . . ? O2 C3 C4 124.0(7) . . ? N1 C3 C4 113.8(7) . . ? C5 C4 C8 119.6(8) . . ? C5 C4 C3 125.5(6) . . ? C8 C4 C3 114.7(7) . . ? C4 C5 C1 116.5(8) . . ? C4 C5 C9 123.2(7) . . ? C1 C5 C9 120.2(7) . . ? N1 C6 C7 112.2(8) . . ? N1 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? N1 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 C4 177.5(8) . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 119.6(8) . . ? C11 C10 N4 119.8(8) . . ? C15 C10 N4 120.6(6) . . ? C12 C11 C10 119.9(8) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C13 C12 C11 120.0(7) . . ? C13 C12 Cl2 121.4(7) . . ? C11 C12 Cl2 118.6(7) . . ? C12 C13 C14 120.6(8) . . ? C12 C13 Cl1 121.1(7) . . ? C14 C13 Cl1 118.3(7) . . ? C15 C14 C13 119.9(9) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C10 120.1(8) . . ? C14 C15 H15 120.0 . . ? C10 C15 H15 120.0 . . ? C2 N1 C3 124.2(7) . . ? C2 N1 C6 120.0(6) . . ? C3 N1 C6 115.6(7) . . ? C8 N2 Cu1 135.2(6) . 1_645 ? N4 N3 C1 123.0(7) . . ? N3 N4 C10 109.7(6) . . ? N3 N4 Cu1 126.9(5) . . ? C10 N4 Cu1 121.7(5) . . ? C2 O1 Cu1 123.7(5) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.080 _refine_diff_density_min -1.697 _refine_diff_density_rms 0.144 #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 760913' #TrackingRef '- 1-5-OK.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 Cl2 Cu N4 O4' _chemical_formula_sum 'C15 H12 Cl2 Cu N4 O4' _chemical_formula_weight 446.73 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 10.500(2) _cell_length_b 14.588(3) _cell_length_c 11.537(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.162(4) _cell_angle_gamma 90.00 _cell_volume 1727.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 415 _cell_measurement_theta_min 2.783 _cell_measurement_theta_max 17.995 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.718 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 900 _exptl_absorpt_coefficient_mu 1.603 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8067 _exptl_absorpt_correction_T_max 0.8561 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. ; _diffrn_ambient_temperature 291(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 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8669 _diffrn_reflns_av_R_equivalents 0.1442 _diffrn_reflns_av_sigmaI/netI 0.2690 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3039 _reflns_number_gt 965 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (BRUKER 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0124P)^2^+1.6600P] 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 3039 _refine_ls_number_parameters 252 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1980 _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 0.767 _refine_ls_restrained_S_all 0.771 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.20725(10) 0.92006(7) 1.01306(10) 0.0593(4) Uani 1 1 d . . . C1 C 0.3943(7) 0.8304(6) 0.8527(7) 0.033(2) Uani 1 1 d . . . C2 C 0.3254(7) 0.7695(5) 0.9180(7) 0.042(2) Uani 1 1 d . . . C3 C 0.4104(8) 0.6356(6) 0.8285(8) 0.049(2) Uani 1 1 d . . . C4 C 0.4757(7) 0.6978(6) 0.7686(7) 0.040(2) Uani 1 1 d . . . C5 C 0.4686(7) 0.7911(6) 0.7789(7) 0.041(2) Uani 1 1 d . . . C6 C 0.2620(15) 0.6137(7) 0.9663(12) 0.087(3) Uani 1 1 d U . . H6A H 0.1803 0.6425 0.9680 0.104 Uiso 1 1 d R . . H6B H 0.2429 0.5585 0.9206 0.104 Uiso 1 1 d R . . C7 C 0.3176(13) 0.5916(9) 1.0679(13) 0.069(4) Uani 0.676(12) 1 d PU . . H7A H 0.2630 0.5503 1.1005 0.103 Uiso 0.676(12) 1 calc PR . . H7B H 0.3343 0.6454 1.1167 0.103 Uiso 0.676(12) 1 calc PR . . H7C H 0.3985 0.5618 1.0654 0.103 Uiso 0.676(12) 1 calc PR . . C8 C 0.5507(8) 0.6559(6) 0.6908(8) 0.051(3) Uani 1 1 d . . . C9 C 0.5413(7) 0.8541(5) 0.7083(7) 0.061(3) Uani 1 1 d . . . H9A H 0.6331 0.8422 0.7307 0.092 Uiso 1 1 calc R . . H9B H 0.5246 0.9169 0.7249 0.092 Uiso 1 1 calc R . . H9C H 0.5117 0.8425 0.6251 0.092 Uiso 1 1 calc R . . C10 C 0.3341(7) 1.0615(6) 0.9246(7) 0.043(2) Uani 1 1 d . . . C11 C 0.2599(7) 1.1019(6) 0.9950(8) 0.050(3) Uani 1 1 d . . . C12 C 0.2565(8) 1.1962(6) 1.0015(8) 0.056(3) Uani 1 1 d . . . H12A H 0.2067 1.2263 1.0513 0.067 Uiso 0.269(4) 1 d PR . . C13 C 0.3247(9) 1.2478(6) 0.9353(9) 0.061(3) Uani 1 1 d . . . C14 C 0.3995(8) 1.2066(7) 0.8652(9) 0.059(3) Uani 1 1 d . . . H14A H 0.4484 1.2427 0.8202 0.071 Uiso 0.731(4) 1 d PR . . C15 C 0.4056(7) 1.1135(6) 0.8617(7) 0.053(3) Uani 1 1 d . . . H15 H 0.4581 1.0850 0.8169 0.063 Uiso 1 1 calc R . . C7' C 0.161(2) 0.586(2) 0.943(3) 0.069(4) Uani 0.324(12) 1 d P . . H7'A H 0.1513 0.5393 0.9997 0.103 Uiso 0.324(12) 1 calc PR . . H7'B H 0.1459 0.5598 0.8653 0.103 Uiso 0.324(12) 1 calc PR . . H7'C H 0.1002 0.6343 0.9456 0.103 Uiso 0.324(12) 1 calc PR . . Cl1 Cl 0.1624(3) 1.2497(2) 1.0870(3) 0.0710(13) Uani 0.731(4) 1 d P . . Cl2 Cl 0.3194(2) 1.36571(15) 0.9425(2) 0.0875(9) Uani 1 1 d . . . Cl1' Cl 0.4614(9) 1.2712(6) 0.7883(9) 0.091(4) Uani 0.269(4) 1 d P . . N1 N 0.3387(6) 0.6767(5) 0.9047(6) 0.049(2) Uani 1 1 d . . . N2 N 0.6126(7) 0.6228(5) 0.6323(7) 0.065(3) Uani 1 1 d . . . N3 N 0.3934(6) 0.9235(5) 0.8563(5) 0.0386(17) Uani 1 1 d . . . N4 N 0.3282(6) 0.9636(4) 0.9221(5) 0.0392(18) Uani 1 1 d . . . O1 O 0.2560(5) 0.7951(3) 0.9868(5) 0.0506(17) Uani 1 1 d . . . O2 O 0.4130(5) 0.5521(4) 0.8200(5) 0.0521(16) Uani 1 1 d . . . O3 O 0.1955(5) 1.0490(4) 1.0568(5) 0.0643(18) Uani 1 1 d . . . O4 O 0.0355(4) 0.9223(4) 0.8558(5) 0.0697(17) Uani 1 1 d . . . H4A H -0.0233 0.9571 0.8720 0.105 Uiso 1 1 d R . . H4B H 0.0044 0.8686 0.8440 0.105 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 Cu1 0.0656(8) 0.0436(7) 0.0758(9) 0.0029(7) 0.0309(6) 0.0013(6) C1 0.037(5) 0.032(5) 0.035(5) -0.001(4) 0.017(4) 0.003(4) C2 0.033(5) 0.032(6) 0.055(7) -0.004(5) 0.001(5) 0.006(4) C3 0.055(6) 0.031(6) 0.056(7) 0.007(6) 0.001(5) 0.003(5) C4 0.037(5) 0.033(6) 0.054(6) -0.008(5) 0.021(5) 0.004(4) C5 0.045(6) 0.034(6) 0.040(6) 0.007(5) -0.003(4) -0.016(4) C6 0.114(11) 0.061(7) 0.097(9) -0.021(7) 0.047(10) 0.015(6) C7 0.065(9) 0.059(7) 0.081(9) -0.019(8) 0.012(9) 0.004(6) C8 0.045(7) 0.029(6) 0.069(8) 0.013(5) -0.007(5) -0.010(5) C9 0.072(7) 0.046(6) 0.072(7) -0.010(5) 0.031(6) 0.000(5) C10 0.035(6) 0.036(6) 0.053(6) -0.001(5) -0.001(5) -0.002(4) C11 0.033(6) 0.051(7) 0.067(7) 0.013(6) 0.012(5) -0.014(5) C12 0.047(7) 0.038(6) 0.072(7) -0.019(6) -0.009(5) 0.005(5) C13 0.062(7) 0.033(6) 0.077(8) 0.000(6) -0.011(6) -0.008(5) C14 0.050(7) 0.050(7) 0.069(8) -0.005(6) -0.007(5) -0.011(5) C15 0.049(6) 0.046(7) 0.058(7) -0.003(5) 0.000(5) -0.011(5) C7' 0.065(9) 0.059(7) 0.081(9) -0.019(8) 0.012(9) 0.004(6) Cl1 0.068(2) 0.045(2) 0.107(3) -0.012(2) 0.033(2) 0.0045(17) Cl2 0.090(2) 0.0299(15) 0.128(3) 0.0005(15) -0.0100(17) -0.0027(13) Cl1' 0.110(9) 0.062(8) 0.097(9) 0.026(6) 0.017(7) -0.037(6) N1 0.059(5) 0.034(5) 0.068(5) -0.001(4) 0.045(4) -0.005(4) N2 0.070(6) 0.048(5) 0.093(7) -0.010(5) 0.050(5) -0.010(4) N3 0.039(4) 0.038(5) 0.039(4) 0.007(4) 0.009(3) 0.005(4) N4 0.039(4) 0.037(5) 0.042(5) 0.005(4) 0.010(4) -0.011(3) O1 0.069(4) 0.023(3) 0.072(4) 0.007(3) 0.043(4) 0.012(3) O2 0.060(4) 0.037(4) 0.065(4) 0.001(3) 0.026(3) 0.005(3) O3 0.062(4) 0.041(4) 0.098(5) -0.017(4) 0.035(4) 0.010(3) O4 0.057(4) 0.050(4) 0.101(5) 0.004(4) 0.014(3) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 1.919(6) . ? Cu1 O1 1.934(5) . ? Cu1 O3 1.959(5) . ? Cu1 N2 1.961(7) 4_576 ? Cu1 O4 2.273(5) . ? C1 N3 1.358(9) . ? C1 C5 1.394(9) . ? C1 C2 1.452(9) . ? C2 O1 1.243(8) . ? C2 N1 1.373(9) . ? C3 O2 1.223(8) . ? C3 C4 1.404(10) . ? C3 N1 1.406(9) . ? C4 C5 1.370(9) . ? C4 C8 1.448(11) . ? C5 C9 1.533(9) . ? C6 C7' 1.11(2) . ? C6 C7 1.237(13) . ? C6 N1 1.496(12) . ? C6 H6A 0.9599 . ? C6 H6B 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N2 1.138(9) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.371(10) . ? C10 C15 1.376(9) . ? C10 N4 1.430(9) . ? C11 O3 1.328(8) . ? C11 C12 1.378(10) . ? C12 C13 1.377(11) . ? C12 Cl1 1.723(9) . ? C12 H12A 0.9599 . ? C13 C14 1.378(10) . ? C13 Cl2 1.723(9) . ? C14 C15 1.360(10) . ? C14 Cl1' 1.530(12) . ? C14 H14A 0.9601 . ? C15 H15 0.9300 . ? C7' H6A 0.8820 . ? C7' H6B 1.0264 . ? C7' H7'A 0.9600 . ? C7' H7'B 0.9600 . ? C7' H7'C 0.9600 . ? Cl1 H12A 0.7641 . ? Cl1' H14A 0.5908 . ? N2 Cu1 1.961(7) 4_675 ? N3 N4 1.268(7) . ? O4 H4A 0.8500 . ? O4 H4B 0.8499 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 O1 89.9(2) . . ? N4 Cu1 O3 84.7(3) . . ? O1 Cu1 O3 168.2(2) . . ? N4 Cu1 N2 168.8(3) . 4_576 ? O1 Cu1 N2 89.9(3) . 4_576 ? O3 Cu1 N2 93.3(3) . 4_576 ? N4 Cu1 O4 93.7(2) . . ? O1 Cu1 O4 94.6(2) . . ? O3 Cu1 O4 96.3(2) . . ? N2 Cu1 O4 97.5(3) 4_576 . ? N3 C1 C5 116.0(7) . . ? N3 C1 C2 126.1(7) . . ? C5 C1 C2 118.0(8) . . ? O1 C2 N1 117.1(7) . . ? O1 C2 C1 124.7(8) . . ? N1 C2 C1 118.2(7) . . ? O2 C3 C4 125.6(9) . . ? O2 C3 N1 119.9(8) . . ? C4 C3 N1 114.5(8) . . ? C5 C4 C3 123.9(7) . . ? C5 C4 C8 121.3(7) . . ? C3 C4 C8 114.7(8) . . ? C4 C5 C1 120.6(7) . . ? C4 C5 C9 120.5(7) . . ? C1 C5 C9 118.9(8) . . ? C7' C6 C7 111(2) . . ? C7' C6 N1 134(2) . . ? C7 C6 N1 114.6(15) . . ? C7' C6 H6A 49.8 . . ? C7 C6 H6A 109.9 . . ? N1 C6 H6A 108.3 . . ? C7' C6 H6B 58.9 . . ? C7 C6 H6B 107.7 . . ? N1 C6 H6B 109.0 . . ? H6A C6 H6B 107.0 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 C4 178.1(10) . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 121.1(8) . . ? C11 C10 N4 114.5(8) . . ? C15 C10 N4 124.5(8) . . ? O3 C11 C10 119.0(9) . . ? O3 C11 C12 121.9(9) . . ? C10 C11 C12 119.1(8) . . ? C13 C12 C11 119.5(8) . . ? C13 C12 Cl1 119.9(8) . . ? C11 C12 Cl1 120.6(8) . . ? C13 C12 H12A 119.7 . . ? C11 C12 H12A 120.9 . . ? C12 C13 C14 121.0(10) . . ? C12 C13 Cl2 119.5(9) . . ? C14 C13 Cl2 119.5(8) . . ? C15 C14 C13 119.3(10) . . ? C15 C14 Cl1' 124.7(10) . . ? C13 C14 Cl1' 115.8(10) . . ? C15 C14 H14A 119.8 . . ? C13 C14 H14A 120.9 . . ? C14 C15 C10 120.0(9) . . ? C14 C15 H15 120.0 . . ? C10 C15 H15 120.0 . . ? C6 C7' H6A 56.2 . . ? C6 C7' H6B 53.2 . . ? H6A C7' H6B 107.7 . . ? C6 C7' H7'A 109.5 . . ? H6A C7' H7'A 119.6 . . ? H6B C7' H7'A 96.7 . . ? C6 C7' H7'B 109.5 . . ? H6A C7' H7'B 130.9 . . ? H6B C7' H7'B 65.9 . . ? H7'A C7' H7'B 109.5 . . ? C6 C7' H7'C 109.5 . . ? H6A C7' H7'C 53.6 . . ? H6B C7' H7'C 153.1 . . ? H7'A C7' H7'C 109.5 . . ? H7'B C7' H7'C 109.5 . . ? C2 N1 C3 124.8(7) . . ? C2 N1 C6 118.4(7) . . ? C3 N1 C6 116.6(7) . . ? C8 N2 Cu1 171.2(8) . 4_675 ? N4 N3 C1 119.2(7) . . ? N3 N4 C10 116.6(6) . . ? N3 N4 Cu1 132.7(5) . . ? C10 N4 Cu1 110.5(5) . . ? C2 O1 Cu1 126.4(5) . . ? C11 O3 Cu1 110.7(5) . . ? Cu1 O4 H4A 108.9 . . ? Cu1 O4 H4B 109.2 . . ? H4A O4 H4B 108.2 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.392 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.101