# 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_1 _database_code_depnum_ccdc_archive 'CCDC 814241' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 Cl Cu N4 O' _chemical_formula_weight 404.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' C C 0.0033 0.0016 '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' H H 0.0000 0.0000 '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 8.1634(10) _cell_length_b 10.2365(13) _cell_length_c 11.6844(15) _cell_angle_alpha 108.091(2) _cell_angle_beta 108.147(2) _cell_angle_gamma 92.647(2) _cell_volume 870.86(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2456 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 24.89 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 414 _exptl_absorpt_coefficient_mu 1.421 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6437 _exptl_absorpt_correction_T_max 0.9071 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6756 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0695 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3369 _reflns_number_gt 2905 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0408P)^2^+1.3693P] 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 3369 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1120 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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 0.88223(6) 0.51880(5) 0.27437(5) 0.00914(16) Uani 1 1 d . . . Cl1 Cl 1.03260(13) 0.72555(11) 0.31019(10) 0.0157(2) Uani 1 1 d . . . O1 O 1.0560(3) 0.4183(3) 0.2275(3) 0.0125(6) Uani 1 1 d . . . N1 N 0.8356(4) 0.3995(4) 0.3661(3) 0.0104(7) Uani 1 1 d . . . N2 N 0.6419(4) 0.5627(3) 0.2320(3) 0.0108(7) Uani 1 1 d . . . N3 N 0.3588(4) 0.5402(3) 0.2035(3) 0.0115(7) Uani 1 1 d . . . H3C H 0.2610 0.5143 0.2094 0.014 Uiso 1 1 calc R . . N4 N 0.4619(5) 0.2247(4) 0.4989(4) 0.0321(10) Uani 1 1 d . . . C1 C 1.0680(5) 0.2876(4) 0.2203(4) 0.0107(8) Uani 1 1 d . . . C2 C 1.1536(5) 0.2096(4) 0.1424(4) 0.0149(9) Uani 1 1 d . . . H2 H 1.1961 0.2496 0.0937 0.018 Uiso 1 1 calc R . . C3 C 1.1769(6) 0.0759(5) 0.1354(4) 0.0194(10) Uani 1 1 d . . . H3 H 1.2379 0.0285 0.0844 0.023 Uiso 1 1 calc R . . C4 C 1.1111(6) 0.0102(5) 0.2029(4) 0.0206(10) Uani 1 1 d . . . H4 H 1.1278 -0.0804 0.1981 0.025 Uiso 1 1 calc R . . C5 C 1.0204(5) 0.0821(4) 0.2771(4) 0.0163(9) Uani 1 1 d . . . H5 H 0.9740 0.0386 0.3217 0.020 Uiso 1 1 calc R . . C6 C 0.9963(5) 0.2197(4) 0.2871(4) 0.0129(9) Uani 1 1 d . . . C7 C 0.8909(5) 0.2838(4) 0.3612(4) 0.0121(9) Uani 1 1 d . . . H7 H 0.8604 0.2366 0.4098 0.015 Uiso 1 1 calc R . . C8 C 0.7173(5) 0.4432(4) 0.4381(4) 0.0114(9) Uani 1 1 d . . . H8A H 0.7533 0.5405 0.4913 0.014 Uiso 1 1 calc R . . H8B H 0.7205 0.3887 0.4933 0.014 Uiso 1 1 calc R . . C9 C 0.5342(5) 0.4213(4) 0.3436(4) 0.0140(9) Uani 1 1 d . . . H9A H 0.5018 0.3241 0.2895 0.017 Uiso 1 1 calc R . . H9B H 0.4540 0.4422 0.3906 0.017 Uiso 1 1 calc R . . C10 C 0.5145(5) 0.5086(4) 0.2606(4) 0.0104(9) Uani 1 1 d . . . C11 C 0.3834(5) 0.6218(4) 0.1334(4) 0.0109(8) Uani 1 1 d . . . C12 C 0.2681(5) 0.6806(4) 0.0569(4) 0.0151(9) Uani 1 1 d . . . H12 H 0.1496 0.6698 0.0450 0.018 Uiso 1 1 calc R . . C13 C 0.3380(6) 0.7562(4) -0.0012(4) 0.0156(9) Uani 1 1 d . . . H13 H 0.2647 0.7973 -0.0536 0.019 Uiso 1 1 calc R . . C14 C 0.5171(6) 0.7725(4) 0.0174(4) 0.0160(9) Uani 1 1 d . . . H14 H 0.5599 0.8251 -0.0223 0.019 Uiso 1 1 calc R . . C15 C 0.6318(5) 0.7122(4) 0.0933(4) 0.0126(9) Uani 1 1 d . . . H15 H 0.7504 0.7228 0.1052 0.015 Uiso 1 1 calc R . . C16 C 0.5614(5) 0.6352(4) 0.1508(4) 0.0118(9) Uani 1 1 d . . . C17 C 0.3066(6) 0.0623(5) 0.5780(5) 0.0262(11) Uani 1 1 d . . . H17A H 0.2156 0.1052 0.6036 0.039 Uiso 1 1 calc R . . H17B H 0.3890 0.0466 0.6496 0.039 Uiso 1 1 calc R . . H17C H 0.2569 -0.0250 0.5097 0.039 Uiso 1 1 calc R . . C18 C 0.3955(6) 0.1537(5) 0.5339(4) 0.0213(10) 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 0.0050(3) 0.0123(3) 0.0134(3) 0.0057(2) 0.0061(2) 0.00218(19) Cl1 0.0106(5) 0.0152(5) 0.0228(6) 0.0084(5) 0.0061(4) -0.0004(4) O1 0.0084(15) 0.0149(16) 0.0171(16) 0.0058(13) 0.0081(12) 0.0021(12) N1 0.0075(17) 0.0152(19) 0.0108(18) 0.0071(15) 0.0036(14) 0.0031(14) N2 0.0084(17) 0.0150(19) 0.0093(18) 0.0040(15) 0.0039(14) 0.0003(14) N3 0.0042(17) 0.0146(19) 0.0153(19) 0.0023(15) 0.0061(14) -0.0014(14) N4 0.029(2) 0.031(3) 0.035(3) 0.012(2) 0.010(2) -0.006(2) C1 0.0045(19) 0.012(2) 0.012(2) 0.0044(17) -0.0020(16) 0.0007(16) C2 0.012(2) 0.016(2) 0.021(2) 0.0066(19) 0.0103(18) -0.0013(17) C3 0.019(2) 0.016(2) 0.023(2) 0.002(2) 0.012(2) 0.0021(19) C4 0.021(3) 0.014(2) 0.027(3) 0.007(2) 0.008(2) 0.0023(19) C5 0.016(2) 0.018(2) 0.020(2) 0.012(2) 0.0082(19) 0.0026(18) C6 0.008(2) 0.018(2) 0.011(2) 0.0030(18) 0.0028(17) -0.0020(17) C7 0.005(2) 0.017(2) 0.012(2) 0.0060(18) 0.0009(16) -0.0025(17) C8 0.007(2) 0.017(2) 0.011(2) 0.0043(18) 0.0046(16) 0.0018(17) C9 0.012(2) 0.015(2) 0.019(2) 0.0060(19) 0.0116(18) 0.0011(17) C10 0.008(2) 0.008(2) 0.012(2) -0.0025(17) 0.0049(16) -0.0011(16) C11 0.011(2) 0.011(2) 0.012(2) 0.0021(17) 0.0068(17) 0.0018(16) C12 0.006(2) 0.020(2) 0.017(2) 0.0048(19) 0.0025(17) 0.0030(17) C13 0.015(2) 0.017(2) 0.014(2) 0.0042(19) 0.0045(18) 0.0075(18) C14 0.020(2) 0.017(2) 0.013(2) 0.0041(19) 0.0101(19) 0.0011(19) C15 0.010(2) 0.015(2) 0.011(2) 0.0018(18) 0.0045(17) -0.0001(17) C16 0.008(2) 0.014(2) 0.010(2) -0.0009(17) 0.0023(16) 0.0026(17) C17 0.029(3) 0.020(3) 0.030(3) 0.005(2) 0.015(2) -0.002(2) C18 0.017(2) 0.020(3) 0.025(3) 0.006(2) 0.006(2) 0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.908(3) . ? Cu1 N1 1.951(3) . ? Cu1 N2 1.977(3) . ? Cu1 Cl1 2.2474(11) . ? O1 C1 1.325(5) . ? N1 C7 1.279(5) . ? N1 C8 1.467(5) . ? N2 C10 1.333(5) . ? N2 C16 1.406(5) . ? N3 C10 1.345(5) . ? N3 C11 1.386(5) . ? N3 H3C 0.8600 . ? N4 C18 1.129(6) . ? C1 C2 1.397(6) . ? C1 C6 1.420(5) . ? C2 C3 1.371(6) . ? C2 H2 0.9300 . ? C3 C4 1.387(6) . ? C3 H3 0.9300 . ? C4 C5 1.377(6) . ? C4 H4 0.9300 . ? C5 C6 1.405(6) . ? C5 H5 0.9300 . ? C6 C7 1.443(6) . ? C7 H7 0.9300 . ? C8 C9 1.514(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.489(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.382(6) . ? C11 C16 1.397(5) . ? C12 C13 1.382(6) . ? C12 H12 0.9300 . ? C13 C14 1.404(6) . ? C13 H13 0.9300 . ? C14 C15 1.386(6) . ? C14 H14 0.9300 . ? C15 C16 1.390(5) . ? C15 H15 0.9300 . ? C17 C18 1.462(6) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N1 93.28(13) . . ? O1 Cu1 N2 150.84(13) . . ? N1 Cu1 N2 92.60(13) . . ? O1 Cu1 Cl1 93.04(9) . . ? N1 Cu1 Cl1 140.88(11) . . ? N2 Cu1 Cl1 100.19(10) . . ? C1 O1 Cu1 125.1(2) . . ? C7 N1 C8 118.4(3) . . ? C7 N1 Cu1 125.1(3) . . ? C8 N1 Cu1 116.3(3) . . ? C10 N2 C16 105.6(3) . . ? C10 N2 Cu1 124.9(3) . . ? C16 N2 Cu1 128.7(3) . . ? C10 N3 C11 108.2(3) . . ? C10 N3 H3C 125.9 . . ? C11 N3 H3C 125.9 . . ? O1 C1 C2 119.3(4) . . ? O1 C1 C6 123.6(4) . . ? C2 C1 C6 117.1(4) . . ? C3 C2 C1 122.0(4) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C2 C3 C4 121.2(4) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 118.4(4) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? C4 C5 C6 121.6(4) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C1 119.6(4) . . ? C5 C6 C7 117.6(4) . . ? C1 C6 C7 122.7(4) . . ? N1 C7 C6 125.9(4) . . ? N1 C7 H7 117.1 . . ? C6 C7 H7 117.1 . . ? N1 C8 C9 108.5(3) . . ? N1 C8 H8A 110.0 . . ? C9 C8 H8A 110.0 . . ? N1 C8 H8B 110.0 . . ? C9 C8 H8B 110.0 . . ? H8A C8 H8B 108.4 . . ? C10 C9 C8 113.6(3) . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? C8 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? N2 C10 N3 112.0(4) . . ? N2 C10 C9 126.1(4) . . ? N3 C10 C9 122.0(3) . . ? C12 C11 N3 131.9(4) . . ? C12 C11 C16 122.5(4) . . ? N3 C11 C16 105.6(3) . . ? C11 C12 C13 116.6(4) . . ? C11 C12 H12 121.7 . . ? C13 C12 H12 121.7 . . ? C12 C13 C14 121.4(4) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C15 C14 C13 121.7(4) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C14 C15 C16 116.9(4) . . ? C14 C15 H15 121.6 . . ? C16 C15 H15 121.6 . . ? C15 C16 C11 120.8(4) . . ? C15 C16 N2 130.5(4) . . ? C11 C16 N2 108.7(3) . . ? C18 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C18 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N4 C18 C17 179.0(5) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.645 _refine_diff_density_min -0.821 _refine_diff_density_rms 0.107 data_2 _database_code_depnum_ccdc_archive 'CCDC 814242' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 Cl Cu N3 O2' _chemical_formula_weight 394.33 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 P21/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 7.087(3) _cell_length_b 15.617(7) _cell_length_c 15.156(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.024(8) _cell_angle_gamma 90.00 _cell_volume 1646.5(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2634 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 23.65 _exptl_crystal_description blocks _exptl_crystal_colour green _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 1.503 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5777 _exptl_absorpt_correction_T_max 0.8642 _exptl_absorpt_process_details 'BRUKER SADABS' _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 DIFFARCTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7822 _diffrn_reflns_av_R_equivalents 0.0606 _diffrn_reflns_av_sigmaI/netI 0.0702 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2901 _reflns_number_gt 2377 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0872P)^2^+5.4412P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2901 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0912 _refine_ls_R_factor_gt 0.0747 _refine_ls_wR_factor_ref 0.1861 _refine_ls_wR_factor_gt 0.1767 _refine_ls_goodness_of_fit_ref 1.083 _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 Cu1 Cu -0.01539(10) 0.54192(5) 0.73409(5) 0.0310(3) Uani 1 1 d . . . Cl1 Cl -0.1395(2) 0.66941(10) 0.76064(12) 0.0416(4) Uani 1 1 d . . . N1 N -0.0041(7) 0.4232(3) 0.7692(3) 0.0323(12) Uani 1 1 d . . . N2 N -0.2803(7) 0.4395(4) 0.4917(4) 0.0355(13) Uani 1 1 d . . . N3 N -0.1671(7) 0.5157(3) 0.6131(3) 0.0303(12) Uani 1 1 d . . . O1 O 0.2362(6) 0.5682(3) 0.7956(3) 0.0372(11) Uani 1 1 d . . . O2 O 0.6030(9) 0.3383(4) 0.3359(4) 0.0601(17) Uani 1 1 d . . . C1 C 0.3625(9) 0.5146(4) 0.8399(4) 0.0323(14) Uani 1 1 d . . . C2 C 0.5458(10) 0.5449(5) 0.8774(5) 0.0438(17) Uani 1 1 d . . . H2 H 0.5731 0.6027 0.8723 0.053 Uiso 1 1 calc R . . C3 C 0.6860(10) 0.4917(5) 0.9213(5) 0.0469(18) Uani 1 1 d . . . H3 H 0.8082 0.5138 0.9424 0.056 Uiso 1 1 calc R . . C4 C 0.6510(10) 0.4048(5) 0.9353(4) 0.0396(16) Uani 1 1 d . . . C5 C 0.4742(9) 0.3749(4) 0.8995(4) 0.0366(15) Uani 1 1 d . . . H5 H 0.4487 0.3171 0.9062 0.044 Uiso 1 1 calc R . . C6 C 0.3265(9) 0.4272(4) 0.8525(4) 0.0306(13) Uani 1 1 d . . . C7 C 0.1457(9) 0.3867(4) 0.8166(4) 0.0311(14) Uani 1 1 d . . . H7 H 0.1354 0.3287 0.8285 0.037 Uiso 1 1 calc R . . C8 C -0.1666(9) 0.3686(4) 0.7337(4) 0.0377(15) Uani 1 1 d . . . H8A H -0.2835 0.3941 0.7463 0.045 Uiso 1 1 calc R . . H8B H -0.1497 0.3133 0.7632 0.045 Uiso 1 1 calc R . . C9 C -0.1854(9) 0.3567(4) 0.6327(4) 0.0345(15) Uani 1 1 d . . . H9A H -0.0714 0.3277 0.6214 0.041 Uiso 1 1 calc R . . H9B H -0.2947 0.3199 0.6113 0.041 Uiso 1 1 calc R . . C10 C -0.2104(8) 0.4380(4) 0.5799(4) 0.0315(14) Uani 1 1 d . . . C11 C -0.2816(8) 0.5237(4) 0.4636(4) 0.0341(15) Uani 1 1 d . . . C12 C -0.3395(9) 0.5622(5) 0.3805(5) 0.0420(17) Uani 1 1 d . . . H12 H -0.3875 0.5298 0.3296 0.050 Uiso 1 1 calc R . . C13 C -0.3237(9) 0.6494(5) 0.3757(5) 0.0462(18) Uani 1 1 d . . . H13 H -0.3616 0.6770 0.3208 0.055 Uiso 1 1 calc R . . C14 C -0.2518(10) 0.6966(5) 0.4520(5) 0.0432(17) Uani 1 1 d . . . H14 H -0.2435 0.7558 0.4470 0.052 Uiso 1 1 calc R . . C15 C -0.1929(9) 0.6600(4) 0.5338(5) 0.0386(16) Uani 1 1 d . . . H15 H -0.1431 0.6930 0.5839 0.046 Uiso 1 1 calc R . . C16 C -0.2092(8) 0.5715(4) 0.5406(4) 0.0323(14) Uani 1 1 d . . . C17 C 0.8107(12) 0.3476(5) 0.9861(5) 0.057(2) Uani 1 1 d . . . H17A H 0.8347 0.3622 1.0488 0.086 Uiso 1 1 calc R . . H17B H 0.9258 0.3560 0.9625 0.086 Uiso 1 1 calc R . . H17C H 0.7719 0.2888 0.9788 0.086 Uiso 1 1 calc R . . H2O H 0.668(11) 0.348(5) 0.289(5) 0.050 Uiso 1 1 d . . . H1O H 0.525(13) 0.332(6) 0.311(6) 0.050 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0322(4) 0.0229(4) 0.0375(5) -0.0023(3) 0.0057(3) -0.0013(3) Cl1 0.0482(10) 0.0284(9) 0.0505(10) -0.0065(7) 0.0149(8) 0.0035(7) N1 0.032(3) 0.032(3) 0.035(3) 0.003(2) 0.010(2) -0.003(2) N2 0.027(3) 0.042(3) 0.041(3) -0.008(2) 0.015(2) 0.000(2) N3 0.028(3) 0.029(3) 0.033(3) -0.007(2) 0.004(2) 0.004(2) O1 0.040(3) 0.025(2) 0.044(3) 0.003(2) 0.002(2) -0.0023(19) O2 0.060(4) 0.066(4) 0.052(4) 0.005(3) 0.003(3) -0.018(3) C1 0.043(4) 0.031(3) 0.024(3) 0.001(3) 0.007(3) 0.003(3) C2 0.047(4) 0.041(4) 0.043(4) -0.007(3) 0.007(3) -0.012(3) C3 0.038(4) 0.055(5) 0.043(4) -0.004(4) -0.005(3) -0.004(3) C4 0.042(4) 0.043(4) 0.033(3) -0.002(3) 0.005(3) 0.003(3) C5 0.041(4) 0.035(4) 0.034(3) -0.003(3) 0.008(3) 0.004(3) C6 0.031(3) 0.033(3) 0.027(3) -0.002(3) 0.006(3) 0.001(3) C7 0.041(4) 0.019(3) 0.034(3) 0.001(3) 0.009(3) 0.000(3) C8 0.035(3) 0.031(4) 0.047(4) 0.001(3) 0.011(3) -0.007(3) C9 0.030(3) 0.027(3) 0.047(4) -0.010(3) 0.010(3) -0.003(3) C10 0.024(3) 0.039(4) 0.033(3) -0.010(3) 0.009(3) 0.000(3) C11 0.023(3) 0.044(4) 0.038(4) -0.003(3) 0.013(3) -0.001(3) C12 0.035(4) 0.057(5) 0.036(4) -0.005(3) 0.012(3) -0.001(3) C13 0.029(3) 0.069(6) 0.041(4) 0.009(4) 0.008(3) 0.007(3) C14 0.038(4) 0.043(4) 0.053(4) 0.007(3) 0.018(3) 0.000(3) C15 0.037(4) 0.038(4) 0.042(4) -0.006(3) 0.012(3) 0.001(3) C16 0.020(3) 0.040(4) 0.038(4) -0.003(3) 0.007(3) 0.001(2) C17 0.057(5) 0.060(5) 0.053(5) -0.001(4) 0.004(4) 0.009(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.892(4) . ? Cu1 N1 1.926(5) . ? Cu1 N3 1.983(5) . ? Cu1 Cl1 2.2440(19) . ? N1 C7 1.294(8) . ? N1 C8 1.451(8) . ? N2 C10 1.333(8) . ? N2 C11 1.382(9) . ? N3 C10 1.327(8) . ? N3 C16 1.390(8) . ? O1 C1 1.312(7) . ? O2 H2O 0.93(8) . ? O2 H1O 0.61(8) . ? C1 C2 1.397(9) . ? C1 C6 1.409(9) . ? C2 C3 1.366(10) . ? C2 H2 0.9300 . ? C3 C4 1.404(10) . ? C3 H3 0.9300 . ? C4 C5 1.350(9) . ? C4 C17 1.528(10) . ? C5 C6 1.409(9) . ? C5 H5 0.9300 . ? C6 C7 1.439(9) . ? C7 H7 0.9300 . ? C8 C9 1.523(9) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.493(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C12 1.386(10) . ? C11 C16 1.398(9) . ? C12 C13 1.370(10) . ? C12 H12 0.9300 . ? C13 C14 1.385(10) . ? C13 H13 0.9300 . ? C14 C15 1.357(10) . ? C14 H14 0.9300 . ? C15 C16 1.391(9) . ? C15 H15 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N1 95.0(2) . . ? O1 Cu1 N3 142.6(2) . . ? N1 Cu1 N3 92.5(2) . . ? O1 Cu1 Cl1 94.82(15) . . ? N1 Cu1 Cl1 143.27(16) . . ? N3 Cu1 Cl1 100.79(15) . . ? C7 N1 C8 117.1(6) . . ? C7 N1 Cu1 124.3(4) . . ? C8 N1 Cu1 118.3(4) . . ? C10 N2 C11 107.7(5) . . ? C10 N3 C16 105.9(5) . . ? C10 N3 Cu1 125.8(4) . . ? C16 N3 Cu1 126.7(4) . . ? C1 O1 Cu1 126.9(4) . . ? H2O O2 H1O 94(10) . . ? O1 C1 C2 118.9(6) . . ? O1 C1 C6 124.3(6) . . ? C2 C1 C6 116.8(6) . . ? C3 C2 C1 121.7(7) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C2 C3 C4 121.9(7) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 116.8(6) . . ? C5 C4 C17 122.8(7) . . ? C3 C4 C17 120.4(6) . . ? C4 C5 C6 123.1(7) . . ? C4 C5 H5 118.5 . . ? C6 C5 H5 118.5 . . ? C5 C6 C1 119.6(6) . . ? C5 C6 C7 117.3(6) . . ? C1 C6 C7 123.0(6) . . ? N1 C7 C6 126.4(6) . . ? N1 C7 H7 116.8 . . ? C6 C7 H7 116.8 . . ? N1 C8 C9 110.8(5) . . ? N1 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C10 C9 C8 114.5(5) . . ? C10 C9 H9A 108.6 . . ? C8 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? C8 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? N3 C10 N2 112.3(6) . . ? N3 C10 C9 125.3(5) . . ? N2 C10 C9 122.4(5) . . ? N2 C11 C12 132.5(6) . . ? N2 C11 C16 105.8(6) . . ? C12 C11 C16 121.7(7) . . ? C13 C12 C11 117.8(7) . . ? C13 C12 H12 121.1 . . ? C11 C12 H12 121.1 . . ? C12 C13 C14 120.4(7) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 122.6(7) . . ? C15 C14 H14 118.7 . . ? C13 C14 H14 118.7 . . ? C14 C15 C16 118.1(6) . . ? C14 C15 H15 121.0 . . ? C16 C15 H15 121.0 . . ? N3 C16 C15 132.3(6) . . ? N3 C16 C11 108.3(6) . . ? C15 C16 C11 119.4(6) . . ? C4 C17 H17A 109.5 . . ? C4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.241 _refine_diff_density_min -0.741 _refine_diff_density_rms 0.146 data_4 _database_code_depnum_ccdc_archive 'CCDC 814243' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H14 Cl2 Cu N4' _chemical_formula_weight 384.74 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 ORTHORHOMBIC _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.657(2) _cell_length_b 12.581(3) _cell_length_c 14.030(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1528.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1565 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 24.86 _exptl_crystal_description BLOCKS _exptl_crystal_colour GREEN _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 1.779 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.4581 _exptl_absorpt_correction_T_max 0.8422 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 DIFFARCTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12346 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_sigmaI/netI 0.0689 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.99 _reflns_number_total 3280 _reflns_number_gt 2993 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0837P)^2^+3.1455P] 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 0.07(3) _refine_ls_number_reflns 3280 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0700 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1459 _refine_ls_wR_factor_gt 0.1415 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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 0.21725(8) 0.62464(5) 0.93246(5) 0.0264(2) Uani 1 1 d . . . Cl1 Cl 0.47956(18) 0.57726(15) 0.87277(11) 0.0392(4) Uani 1 1 d . . . Cl2 Cl 0.06099(19) 0.57398(13) 0.81073(11) 0.0368(4) Uani 1 1 d . . . N1 N 0.2318(6) 0.7741(4) 0.8740(4) 0.0315(11) Uani 1 1 d . . . N2 N 0.2818(7) 0.7121(4) 1.0467(3) 0.0340(11) Uani 1 1 d . . . N3 N 0.1594(6) 0.5020(4) 1.0182(3) 0.0291(11) Uani 1 1 d . . . N4 N 0.0978(7) 0.4176(5) 1.1517(3) 0.0353(12) Uani 1 1 d . . . H4C H 0.0826 0.4064 1.2115 0.042 Uiso 1 1 calc R . . C1 C 0.2163(9) 0.8028(5) 0.7832(5) 0.0375(14) Uani 1 1 d . . . H1 H 0.1968 0.7502 0.7383 0.045 Uiso 1 1 calc R . . C2 C 0.2277(9) 0.9062(5) 0.7521(5) 0.0427(16) Uani 1 1 d . . . H2 H 0.2192 0.9225 0.6877 0.051 Uiso 1 1 calc R . . C3 C 0.2519(8) 0.9849(6) 0.8182(6) 0.0466(18) Uani 1 1 d . . . H3 H 0.2566 1.0556 0.7992 0.056 Uiso 1 1 calc R . . C4 C 0.2693(8) 0.9581(5) 0.9136(5) 0.0401(16) Uani 1 1 d . . . H4 H 0.2869 1.0099 0.9597 0.048 Uiso 1 1 calc R . . C5 C 0.2596(7) 0.8515(5) 0.9378(5) 0.0349(14) Uani 1 1 d . . . C6 C 0.2893(8) 0.8104(5) 1.0343(4) 0.0341(13) Uani 1 1 d . . . H6 H 0.3129 0.8560 1.0844 0.041 Uiso 1 1 calc R . . C7 C 0.3093(9) 0.6676(6) 1.1410(4) 0.0437(17) Uani 1 1 d . . . H7A H 0.3305 0.7243 1.1861 0.052 Uiso 1 1 calc R . . H7B H 0.3980 0.6206 1.1393 0.052 Uiso 1 1 calc R . . C8 C 0.1671(8) 0.6065(5) 1.1719(4) 0.0357(15) Uani 1 1 d . . . H8A H 0.1781 0.5862 1.2383 0.043 Uiso 1 1 calc R . . H8B H 0.0773 0.6523 1.1667 0.043 Uiso 1 1 calc R . . C9 C 0.1420(7) 0.5091(5) 1.1131(4) 0.0306(13) Uani 1 1 d . . . C10 C 0.1198(7) 0.3964(5) 0.9974(4) 0.0306(14) Uani 1 1 d . . . C11 C 0.0804(8) 0.3440(5) 1.0808(5) 0.0336(14) Uani 1 1 d . . . C12 C 0.0332(8) 0.2390(6) 1.0817(5) 0.0426(17) Uani 1 1 d . . . H12 H 0.0071 0.2054 1.1385 0.051 Uiso 1 1 calc R . . C14 C 0.0673(10) 0.2367(6) 0.9123(6) 0.0464(18) Uani 1 1 d . . . H14 H 0.0630 0.1991 0.8553 0.056 Uiso 1 1 calc R . . C15 C 0.1146(9) 0.3423(5) 0.9117(4) 0.0375(16) Uani 1 1 d . . . H15 H 0.1422 0.3756 0.8551 0.045 Uiso 1 1 calc R . . C13 C 0.0261(10) 0.1864(5) 0.9971(6) 0.0480(19) Uani 1 1 d . . . H13 H -0.0067 0.1160 0.9959 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0342(4) 0.0303(3) 0.0147(3) 0.0001(3) -0.0001(3) -0.0029(3) Cl1 0.0355(8) 0.0607(10) 0.0214(7) -0.0042(7) 0.0002(6) 0.0069(7) Cl2 0.0449(8) 0.0396(8) 0.0260(8) 0.0004(6) -0.0100(6) -0.0071(7) N1 0.029(3) 0.034(3) 0.031(3) 0.003(2) 0.002(2) -0.001(2) N2 0.038(3) 0.042(3) 0.022(3) -0.006(2) -0.004(2) -0.004(3) N3 0.040(3) 0.033(3) 0.014(2) -0.002(2) 0.000(2) -0.007(2) N4 0.047(3) 0.045(3) 0.014(2) 0.005(2) 0.001(2) -0.006(3) C1 0.041(3) 0.039(3) 0.033(3) 0.005(3) -0.001(3) 0.006(3) C2 0.043(4) 0.041(4) 0.044(4) 0.016(3) -0.001(3) 0.008(3) C3 0.038(4) 0.031(3) 0.071(5) 0.006(3) 0.000(3) 0.001(3) C4 0.040(4) 0.034(3) 0.046(4) -0.003(3) 0.000(3) -0.002(3) C5 0.029(3) 0.032(3) 0.044(4) -0.005(3) 0.001(3) -0.001(2) C6 0.033(3) 0.037(3) 0.032(3) -0.007(2) 0.001(3) -0.004(3) C7 0.052(4) 0.057(4) 0.022(3) -0.006(3) -0.013(3) -0.008(4) C8 0.049(4) 0.046(4) 0.011(2) -0.004(2) -0.008(2) -0.001(3) C9 0.031(3) 0.040(3) 0.021(3) -0.006(3) -0.003(2) 0.006(3) C10 0.030(3) 0.040(4) 0.021(3) 0.006(2) -0.006(2) 0.002(3) C11 0.039(3) 0.034(3) 0.028(3) 0.004(3) 0.000(3) 0.000(3) C12 0.048(4) 0.044(4) 0.035(4) 0.011(3) 0.000(3) -0.009(3) C14 0.058(5) 0.038(4) 0.043(4) -0.004(3) -0.006(3) 0.003(3) C15 0.066(5) 0.034(3) 0.013(3) 0.003(2) 0.004(3) 0.004(3) C13 0.062(5) 0.027(4) 0.054(5) 0.004(3) -0.007(4) -0.008(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 N3 2.019(5) . ? Cu1 N2 2.023(5) . ? Cu1 N1 2.055(5) . ? Cu1 Cl2 2.2700(17) . ? Cu1 Cl1 2.4928(18) . ? N1 C1 1.331(8) . ? N1 C5 1.344(8) . ? N2 C6 1.251(8) . ? N2 C7 1.457(8) . ? N3 C9 1.343(7) . ? N3 C10 1.404(8) . ? N4 C9 1.329(9) . ? N4 C11 1.368(8) . ? N4 H4C 0.8600 . ? C1 C2 1.375(9) . ? C1 H1 0.9300 . ? C2 C3 1.372(11) . ? C2 H2 0.9300 . ? C3 C4 1.389(10) . ? C3 H3 0.9300 . ? C4 C5 1.387(9) . ? C4 H4 0.9300 . ? C5 C6 1.473(9) . ? C6 H6 0.9300 . ? C7 C8 1.515(10) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.493(9) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 C15 1.382(8) . ? C10 C11 1.385(8) . ? C11 C12 1.382(9) . ? C12 C13 1.360(11) . ? C12 H12 0.9300 . ? C14 C15 1.390(10) . ? C14 C13 1.394(11) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C13 H13 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N2 90.7(2) . . ? N3 Cu1 N1 162.1(2) . . ? N2 Cu1 N1 78.6(2) . . ? N3 Cu1 Cl2 94.94(15) . . ? N2 Cu1 Cl2 156.00(18) . . ? N1 Cu1 Cl2 89.59(16) . . ? N3 Cu1 Cl1 104.09(16) . . ? N2 Cu1 Cl1 98.30(18) . . ? N1 Cu1 Cl1 91.66(15) . . ? Cl2 Cu1 Cl1 102.89(7) . . ? C1 N1 C5 117.3(5) . . ? C1 N1 Cu1 128.7(5) . . ? C5 N1 Cu1 114.1(4) . . ? C6 N2 C7 119.8(5) . . ? C6 N2 Cu1 116.3(4) . . ? C7 N2 Cu1 123.8(4) . . ? C9 N3 C10 104.0(5) . . ? C9 N3 Cu1 124.6(5) . . ? C10 N3 Cu1 131.3(4) . . ? C9 N4 C11 108.7(5) . . ? C9 N4 H4C 125.6 . . ? C11 N4 H4C 125.6 . . ? N1 C1 C2 123.6(7) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C3 C2 C1 118.6(7) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 119.5(6) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 117.6(6) . . ? C3 C4 H4 121.2 . . ? C5 C4 H4 121.2 . . ? N1 C5 C4 123.3(7) . . ? N1 C5 C6 112.9(5) . . ? C4 C5 C6 123.6(6) . . ? N2 C6 C5 117.7(6) . . ? N2 C6 H6 121.1 . . ? C5 C6 H6 121.1 . . ? N2 C7 C8 108.8(5) . . ? N2 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? N2 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C9 C8 C7 112.2(6) . . ? C9 C8 H8A 109.2 . . ? C7 C8 H8A 109.2 . . ? C9 C8 H8B 109.2 . . ? C7 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? N4 C9 N3 112.3(6) . . ? N4 C9 C8 121.9(5) . . ? N3 C9 C8 125.8(6) . . ? C15 C10 C11 119.5(6) . . ? C15 C10 N3 130.9(6) . . ? C11 C10 N3 109.6(5) . . ? N4 C11 C12 132.2(6) . . ? N4 C11 C10 105.4(5) . . ? C12 C11 C10 122.3(6) . . ? C13 C12 C11 118.1(7) . . ? C13 C12 H12 121.0 . . ? C11 C12 H12 121.0 . . ? C15 C14 C13 121.0(7) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C10 C15 C14 118.3(6) . . ? C10 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? C12 C13 C14 120.8(6) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.868 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.122 data_6 _database_code_depnum_ccdc_archive 'CCDC 814244' #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Cu Complex' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 Cl2 Cu N4 O2' _chemical_formula_weight 484.86 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n 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 10.3104(5) _cell_length_b 17.1202(9) _cell_length_c 11.9361(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.781(3) _cell_angle_gamma 90.00 _cell_volume 2106.72(18) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1865 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 25.67 _exptl_crystal_description Bocks _exptl_crystal_colour GREEN _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 996 _exptl_absorpt_coefficient_mu 1.314 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6635 _exptl_absorpt_correction_T_max 0.8582 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; Hydrogen atoms H1W and H2W attached to O1W is located from the difference FOurier map and the distace between O1W-H1W,O2W-H2W and H1W-H2W is restrained using DIFX command at 0.97 and 1.53 A respectively ; _diffrn_ambient_temperature 296(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 DIFFARCTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21882 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 27.73 _reflns_number_total 4949 _reflns_number_gt 3206 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0428P)^2^+0.3350P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4949 _refine_ls_number_parameters 272 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0740 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.0877 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 C20 C 0.5441(4) 0.2631(2) 0.4784(4) 0.1062(15) Uani 1 1 d . . . H20A H 0.4686 0.2832 0.4404 0.159 Uiso 1 1 calc R . . H20B H 0.6075 0.2480 0.4244 0.159 Uiso 1 1 calc R . . H20C H 0.5799 0.3028 0.5266 0.159 Uiso 1 1 calc R . . O1 O 0.5099(3) 0.19838(16) 0.5423(3) 0.1008(9) Uani 1 1 d . . . H1O H 0.4476 0.2094 0.5813 0.151 Uiso 1 1 calc R . . C1 C 0.5704(3) 0.08745(17) 0.2361(3) 0.0572(8) Uani 1 1 d . . . H1 H 0.5532 0.1393 0.2538 0.069 Uiso 1 1 calc R . . C2 C 0.5529(3) 0.03042(19) 0.3140(3) 0.0715(10) Uani 1 1 d . . . H2 H 0.5222 0.0435 0.3845 0.086 Uiso 1 1 calc R . . C3 C 0.5805(3) -0.0475(2) 0.2893(4) 0.0886(13) Uani 1 1 d . . . H3 H 0.5695 -0.0854 0.3441 0.106 Uiso 1 1 calc R . . C4 C 0.6227(3) -0.0686(2) 0.1873(4) 0.0843(13) Uani 1 1 d . . . H4 H 0.6404 -0.1208 0.1722 0.101 Uiso 1 1 calc R . . C5 C 0.6400(3) -0.01168(18) 0.1036(3) 0.0654(9) Uani 1 1 d . . . C6 C 0.6148(2) 0.06781(16) 0.1286(3) 0.0499(7) Uani 1 1 d . . . C7 C 0.6806(3) -0.0313(2) -0.0051(4) 0.0825(12) Uani 1 1 d . . . H7 H 0.6986 -0.0829 -0.0235 0.099 Uiso 1 1 calc R . . C8 C 0.6930(3) 0.0265(2) -0.0831(3) 0.0723(10) Uani 1 1 d . . . H8 H 0.7183 0.0147 -0.1556 0.087 Uiso 1 1 calc R . . C9 C 0.6674(3) 0.10303(17) -0.0528(3) 0.0543(8) Uani 1 1 d . . . C10 C 0.6746(3) 0.1666(2) -0.1348(3) 0.0583(8) Uani 1 1 d . . . H10 H 0.6953 0.1569 -0.2091 0.070 Uiso 1 1 calc R . . C11 C 0.6491(3) 0.30170(19) -0.1774(3) 0.0647(9) Uani 1 1 d . . . H11A H 0.5601 0.3175 -0.1920 0.078 Uiso 1 1 calc R . . H11B H 0.6873 0.2866 -0.2480 0.078 Uiso 1 1 calc R . . C12 C 0.7231(3) 0.3683(2) -0.1278(3) 0.0660(9) Uani 1 1 d . . . H12A H 0.8118 0.3515 -0.1143 0.079 Uiso 1 1 calc R . . H12B H 0.7253 0.4103 -0.1823 0.079 Uiso 1 1 calc R . . C13 C 0.6710(2) 0.39959(16) -0.0218(2) 0.0482(7) Uani 1 1 d . . . C14 C 0.5864(3) 0.40961(15) 0.1444(2) 0.0455(6) Uani 1 1 d . . . C15 C 0.5335(3) 0.39720(17) 0.2488(2) 0.0534(7) Uani 1 1 d . . . H15 H 0.5090 0.3475 0.2720 0.064 Uiso 1 1 calc R . . C16 C 0.5185(3) 0.46139(19) 0.3170(3) 0.0613(8) Uani 1 1 d . . . H16 H 0.4820 0.4550 0.3873 0.074 Uiso 1 1 calc R . . C17 C 0.5566(3) 0.53552(19) 0.2834(3) 0.0699(10) Uani 1 1 d . . . H17 H 0.5458 0.5773 0.3321 0.084 Uiso 1 1 calc R . . C18 C 0.6091(3) 0.54876(18) 0.1818(3) 0.0652(9) Uani 1 1 d . . . H18 H 0.6347 0.5985 0.1599 0.078 Uiso 1 1 calc R . . C19 C 0.6230(3) 0.48480(16) 0.1119(3) 0.0516(7) Uani 1 1 d . . . N1 N 0.63047(19) 0.12438(13) 0.04902(19) 0.0452(5) Uani 1 1 d . . . N2 N 0.6515(2) 0.23557(14) -0.1003(2) 0.0513(6) Uani 1 1 d . . . N3 N 0.6178(2) 0.35747(12) 0.05928(18) 0.0446(5) Uani 1 1 d . . . N4 N 0.6756(2) 0.47551(13) 0.0070(2) 0.0584(7) Uani 1 1 d . . . H4N H 0.7065 0.5124 -0.0336 0.070 Uiso 1 1 calc R . . Cl1 Cl 0.78863(8) 0.24108(4) 0.19836(7) 0.0575(2) Uani 1 1 d . . . Cl2 Cl 0.39335(7) 0.23505(4) 0.11230(7) 0.0593(2) Uani 1 1 d . . . Cu1 Cu 0.61473(3) 0.242474(17) 0.06774(3) 0.04059(12) Uani 1 1 d . . . O1W O 0.7307(2) 0.10939(12) 0.5958(2) 0.0679(6) Uani 1 1 d D . . H1W H 0.799(3) 0.149(2) 0.595(4) 0.20(2) Uiso 1 1 d D . . H2W H 0.657(2) 0.138(2) 0.566(3) 0.115(15) Uiso 1 1 d 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 C20 0.103(3) 0.112(4) 0.104(3) 0.050(3) 0.005(3) -0.017(3) O1 0.093(2) 0.082(2) 0.128(2) 0.0327(17) 0.0288(17) 0.0143(15) C1 0.0481(18) 0.0419(16) 0.081(2) 0.0146(15) -0.0056(16) -0.0031(13) C2 0.056(2) 0.061(2) 0.098(3) 0.0326(19) -0.0097(18) -0.0042(16) C3 0.058(2) 0.060(2) 0.146(4) 0.051(3) -0.034(2) -0.0180(18) C4 0.054(2) 0.0391(19) 0.159(4) 0.015(2) -0.035(2) -0.0021(16) C5 0.0339(16) 0.0385(16) 0.123(3) -0.0029(18) -0.0227(18) -0.0012(13) C6 0.0322(15) 0.0351(15) 0.082(2) 0.0021(14) -0.0120(14) -0.0041(11) C7 0.046(2) 0.046(2) 0.155(4) -0.035(2) -0.018(2) 0.0064(16) C8 0.0451(19) 0.062(2) 0.109(3) -0.040(2) -0.0070(18) 0.0057(16) C9 0.0333(15) 0.0495(17) 0.080(2) -0.0231(16) -0.0024(14) 0.0015(13) C10 0.0460(18) 0.074(2) 0.0551(18) -0.0192(16) 0.0039(14) -0.0021(16) C11 0.068(2) 0.078(2) 0.0484(18) 0.0124(16) 0.0112(16) 0.0096(18) C12 0.0537(19) 0.076(2) 0.069(2) 0.0252(18) 0.0106(16) -0.0029(17) C13 0.0357(15) 0.0441(16) 0.0649(18) 0.0169(14) -0.0021(13) -0.0034(12) C14 0.0379(15) 0.0355(14) 0.0629(18) -0.0003(13) -0.0078(13) 0.0027(12) C15 0.0520(18) 0.0460(17) 0.0621(18) -0.0045(14) 0.0004(14) 0.0010(13) C16 0.054(2) 0.062(2) 0.068(2) -0.0140(16) -0.0062(16) 0.0038(16) C17 0.056(2) 0.051(2) 0.102(3) -0.0247(19) -0.0193(19) 0.0102(16) C18 0.0506(19) 0.0361(16) 0.108(3) 0.0003(17) -0.0206(19) 0.0010(14) C19 0.0398(16) 0.0394(15) 0.075(2) 0.0090(14) -0.0111(15) 0.0019(12) N1 0.0344(12) 0.0344(12) 0.0666(15) -0.0059(11) -0.0022(11) -0.0020(9) N2 0.0411(13) 0.0636(16) 0.0493(13) -0.0032(12) 0.0028(10) 0.0013(11) N3 0.0417(13) 0.0366(12) 0.0555(14) 0.0074(10) 0.0005(11) -0.0001(10) N4 0.0479(15) 0.0415(14) 0.0854(19) 0.0236(13) -0.0102(13) -0.0081(11) Cl1 0.0594(5) 0.0408(4) 0.0718(5) 0.0020(3) -0.0187(4) -0.0031(3) Cl2 0.0390(4) 0.0454(4) 0.0937(6) 0.0032(4) 0.0116(4) -0.0003(3) Cu1 0.0406(2) 0.03340(18) 0.04787(19) 0.00115(14) 0.00427(14) -0.00085(13) O1W 0.0680(15) 0.0468(13) 0.0891(17) -0.0174(11) 0.0031(13) 0.0017(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 C20 O1 1.393(4) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? O1 H1O 0.8200 . ? C1 C2 1.362(4) . ? C1 C6 1.409(4) . ? C1 H1 0.9300 . ? C2 C3 1.396(5) . ? C2 H2 0.9300 . ? C3 C4 1.348(5) . ? C3 H3 0.9300 . ? C4 C5 1.410(5) . ? C4 H4 0.9300 . ? C5 C7 1.409(5) . ? C5 C6 1.418(4) . ? C6 N1 1.367(3) . ? C7 C8 1.366(5) . ? C7 H7 0.9300 . ? C8 C9 1.385(4) . ? C8 H8 0.9300 . ? C9 N1 1.330(3) . ? C9 C10 1.466(4) . ? C10 N2 1.274(4) . ? C10 H10 0.9300 . ? C11 N2 1.458(4) . ? C11 C12 1.490(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.482(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N3 1.330(3) . ? C13 N4 1.345(3) . ? C14 C15 1.384(4) . ? C14 N3 1.394(3) . ? C14 C19 1.398(4) . ? C15 C16 1.378(4) . ? C15 H15 0.9300 . ? C16 C17 1.390(5) . ? C16 H16 0.9300 . ? C17 C18 1.354(4) . ? C17 H17 0.9300 . ? C18 C19 1.385(4) . ? C18 H18 0.9300 . ? C19 N4 1.380(4) . ? N1 Cu1 2.041(2) . ? N2 Cu1 2.050(2) . ? N3 Cu1 1.972(2) . ? N4 H4N 0.8600 . ? Cl1 Cu1 2.3600(8) . ? Cl2 Cu1 2.3541(7) . ? O1W H1W 0.974(19) . ? O1W H2W 0.972(18) . ? 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 C20 H20A 109.5 . . ? O1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C20 O1 H1O 109.5 . . ? C2 C1 C6 119.9(3) . . ? C2 C1 H1 120.0 . . ? C6 C1 H1 120.0 . . ? C1 C2 C3 120.7(4) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 121.1(4) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 120.0(4) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C7 C5 C4 122.0(3) . . ? C7 C5 C6 118.7(3) . . ? C4 C5 C6 119.3(4) . . ? N1 C6 C1 120.4(3) . . ? N1 C6 C5 120.7(3) . . ? C1 C6 C5 118.9(3) . . ? C8 C7 C5 119.1(3) . . ? C8 C7 H7 120.5 . . ? C5 C7 H7 120.5 . . ? C7 C8 C9 119.2(3) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? N1 C9 C8 123.8(3) . . ? N1 C9 C10 115.1(2) . . ? C8 C9 C10 121.0(3) . . ? N2 C10 C9 117.4(3) . . ? N2 C10 H10 121.3 . . ? C9 C10 H10 121.3 . . ? N2 C11 C12 109.8(3) . . ? N2 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? N2 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C13 C12 C11 115.2(2) . . ? C13 C12 H12A 108.5 . . ? C11 C12 H12A 108.5 . . ? C13 C12 H12B 108.5 . . ? C11 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? N3 C13 N4 110.6(3) . . ? N3 C13 C12 125.6(3) . . ? N4 C13 C12 123.7(3) . . ? C15 C14 N3 131.0(2) . . ? C15 C14 C19 120.2(3) . . ? N3 C14 C19 108.7(2) . . ? C16 C15 C14 117.3(3) . . ? C16 C15 H15 121.4 . . ? C14 C15 H15 121.4 . . ? C15 C16 C17 121.5(3) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C18 C17 C16 122.0(3) . . ? C18 C17 H17 119.0 . . ? C16 C17 H17 119.0 . . ? C17 C18 C19 116.9(3) . . ? C17 C18 H18 121.5 . . ? C19 C18 H18 121.5 . . ? N4 C19 C18 133.0(3) . . ? N4 C19 C14 104.9(2) . . ? C18 C19 C14 122.0(3) . . ? C9 N1 C6 118.5(2) . . ? C9 N1 Cu1 113.37(19) . . ? C6 N1 Cu1 127.98(19) . . ? C10 N2 C11 121.2(3) . . ? C10 N2 Cu1 114.0(2) . . ? C11 N2 Cu1 124.8(2) . . ? C13 N3 C14 106.6(2) . . ? C13 N3 Cu1 125.85(19) . . ? C14 N3 Cu1 126.73(17) . . ? C13 N4 C19 109.2(2) . . ? C13 N4 H4N 125.4 . . ? C19 N4 H4N 125.4 . . ? N3 Cu1 N1 169.19(9) . . ? N3 Cu1 N2 90.23(9) . . ? N1 Cu1 N2 79.61(9) . . ? N3 Cu1 Cl2 94.70(6) . . ? N1 Cu1 Cl2 92.87(6) . . ? N2 Cu1 Cl2 114.24(7) . . ? N3 Cu1 Cl1 91.79(6) . . ? N1 Cu1 Cl1 90.08(6) . . ? N2 Cu1 Cl1 119.81(7) . . ? Cl2 Cu1 Cl1 125.48(3) . . ? H1W O1W H2W 102(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 C6 C1 C2 C3 1.1(5) . . . . ? C1 C2 C3 C4 -1.3(5) . . . . ? C2 C3 C4 C5 0.1(5) . . . . ? C3 C4 C5 C7 -178.3(3) . . . . ? C3 C4 C5 C6 1.1(5) . . . . ? C2 C1 C6 N1 178.8(3) . . . . ? C2 C1 C6 C5 0.2(4) . . . . ? C7 C5 C6 N1 -0.5(4) . . . . ? C4 C5 C6 N1 -179.9(3) . . . . ? C7 C5 C6 C1 178.1(3) . . . . ? C4 C5 C6 C1 -1.3(4) . . . . ? C4 C5 C7 C8 178.7(3) . . . . ? C6 C5 C7 C8 -0.7(5) . . . . ? C5 C7 C8 C9 1.0(5) . . . . ? C7 C8 C9 N1 -0.2(5) . . . . ? C7 C8 C9 C10 -177.6(3) . . . . ? N1 C9 C10 N2 3.3(4) . . . . ? C8 C9 C10 N2 -179.1(3) . . . . ? N2 C11 C12 C13 -62.0(4) . . . . ? C11 C12 C13 N3 36.9(4) . . . . ? C11 C12 C13 N4 -145.6(3) . . . . ? N3 C14 C15 C16 177.3(3) . . . . ? C19 C14 C15 C16 0.4(4) . . . . ? C14 C15 C16 C17 -1.0(5) . . . . ? C15 C16 C17 C18 0.7(5) . . . . ? C16 C17 C18 C19 0.2(5) . . . . ? C17 C18 C19 N4 -177.1(3) . . . . ? C17 C18 C19 C14 -0.8(4) . . . . ? C15 C14 C19 N4 177.7(2) . . . . ? N3 C14 C19 N4 0.2(3) . . . . ? C15 C14 C19 C18 0.5(4) . . . . ? N3 C14 C19 C18 -177.1(3) . . . . ? C8 C9 N1 C6 -0.9(4) . . . . ? C10 C9 N1 C6 176.6(2) . . . . ? C8 C9 N1 Cu1 175.6(2) . . . . ? C10 C9 N1 Cu1 -6.9(3) . . . . ? C1 C6 N1 C9 -177.3(2) . . . . ? C5 C6 N1 C9 1.3(4) . . . . ? C1 C6 N1 Cu1 6.8(4) . . . . ? C5 C6 N1 Cu1 -174.65(19) . . . . ? C9 C10 N2 C11 -176.4(2) . . . . ? C9 C10 N2 Cu1 2.1(3) . . . . ? C12 C11 N2 C10 -134.5(3) . . . . ? C12 C11 N2 Cu1 47.1(3) . . . . ? N4 C13 N3 C14 0.2(3) . . . . ? C12 C13 N3 C14 178.0(3) . . . . ? N4 C13 N3 Cu1 -169.64(17) . . . . ? C12 C13 N3 Cu1 8.2(4) . . . . ? C15 C14 N3 C13 -177.5(3) . . . . ? C19 C14 N3 C13 -0.3(3) . . . . ? C15 C14 N3 Cu1 -7.7(4) . . . . ? C19 C14 N3 Cu1 169.51(18) . . . . ? N3 C13 N4 C19 -0.1(3) . . . . ? C12 C13 N4 C19 -178.0(3) . . . . ? C18 C19 N4 C13 176.8(3) . . . . ? C14 C19 N4 C13 0.0(3) . . . . ? C13 N3 Cu1 N1 0.9(6) . . . . ? C14 N3 Cu1 N1 -167.0(4) . . . . ? C13 N3 Cu1 N2 -19.1(2) . . . . ? C14 N3 Cu1 N2 173.0(2) . . . . ? C13 N3 Cu1 Cl2 -133.4(2) . . . . ? C14 N3 Cu1 Cl2 58.7(2) . . . . ? C13 N3 Cu1 Cl1 100.7(2) . . . . ? C14 N3 Cu1 Cl1 -67.1(2) . . . . ? C9 N1 Cu1 N3 -14.1(6) . . . . ? C6 N1 Cu1 N3 161.9(4) . . . . ? C9 N1 Cu1 N2 6.18(18) . . . . ? C6 N1 Cu1 N2 -177.7(2) . . . . ? C9 N1 Cu1 Cl2 120.31(18) . . . . ? C6 N1 Cu1 Cl2 -63.6(2) . . . . ? C9 N1 Cu1 Cl1 -114.16(18) . . . . ? C6 N1 Cu1 Cl1 61.9(2) . . . . ? C10 N2 Cu1 N3 171.8(2) . . . . ? C11 N2 Cu1 N3 -9.7(2) . . . . ? C10 N2 Cu1 N1 -4.4(2) . . . . ? C11 N2 Cu1 N1 174.0(2) . . . . ? C10 N2 Cu1 Cl2 -92.9(2) . . . . ? C11 N2 Cu1 Cl2 85.6(2) . . . . ? C10 N2 Cu1 Cl1 79.6(2) . . . . ? C11 N2 Cu1 Cl1 -101.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.73 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.431 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.059