Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 222 _publ_requested_journal 'Dalton Trans.' _publ_contact_author_name ' Paul H. Walton' _publ_contact_author_address ; Department of Chemistry University of York Heslington York YO10 5DD UK ; _publ_contact_author_email phw2@york.ac.uk _publ_contact_author_phone '+44 (1904) 432500' _publ_contact_author_fax '+44 (1904) 432516' loop_ _publ_author_name _publ_author_address 'Nairn, Alison K.' ;Department of Chemistry University of York Heslington York YO10 5DD UK ; 'Bhalla, Rajiv' ;Department of Chemistry University of York Heslington York YO10 5DD UK ; 'Boxwell, Clive J.' ;Department of Chemistry University of York Heslington York YO10 5DD UK ; 'Whitwood, Adrian C.' ;Department of Chemistry University of York Heslington York YO10 5DD UK ; 'Walton, Paul H.' ;Department of Chemistry University of York Heslington York YO10 5DD UK ; _publ_section_title ; Syntheses and structures of copper(I) cis-1,3,5-tri-iminocyclohexane complexes ; data_shelx _database_code_depnum_ccdc_archive 'CCDC 279581' #------------------------------------------------------------------------------ _audit_creation_date 1998-08-25 _audit_creation_method SHELXL-97 _audit_update_record ; ? ; #------------------------------------------------------------------------------ #CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H33 Cl Cu N3' _chemical_formula_sum 'C33 H33 Cl Cu N3' _chemical_formula_weight 570.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 21.873(7) _cell_length_b 22.840(4) _cell_length_c 12.268(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6129(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 4.455 _cell_measurement_theta_max 5.875 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2384 _exptl_absorpt_coefficient_mu 0.825 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.912 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_special_details ; The scan width was (1.00+0.34tan\q)\% with an \w scan speed of 4\% per minute (up to 5 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'RIGAKU AFC6S' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% -0.97 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -3 -3 -2 -4 -2 -1 -1 -4 -2 _diffrn_reflns_number 4788 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.3269 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 24.98 _reflns_number_total 4258 _reflns_number_gt 1047 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.00868 _diffrn_orient_matrix_UB_12 -0.04265 _diffrn_orient_matrix_UB_13 0.00998 _diffrn_orient_matrix_UB_21 -0.03898 _diffrn_orient_matrix_UB_22 0.00987 _diffrn_orient_matrix_UB_23 0.03844 _diffrn_orient_matrix_UB_31 -0.02227 _diffrn_orient_matrix_UB_32 -0.00065 _diffrn_orient_matrix_UB_33 -0.07118 _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' _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^)+(0.0627P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4258 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3245 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1915 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 0.926 _refine_ls_restrained_S_all 0.926 _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 0.23217(6) 0.40737(6) 0.98066(10) 0.0739(5) Uani 1 1 d . . . Cl1 Cl 0.17780(11) 0.37338(11) 1.12661(19) 0.0592(8) Uani 1 1 d . . . N1 N 0.2168(5) 0.4891(5) 0.9114(7) 0.073(3) Uani 1 1 d . . . N2 N 0.2334(5) 0.3676(5) 0.8276(7) 0.077(3) Uani 1 1 d . . . N3 N 0.3268(4) 0.4135(4) 0.9877(9) 0.073(3) Uani 1 1 d . . . C1 C 0.2604(6) 0.5023(5) 0.8222(10) 0.078(4) Uani 1 1 d . . . H1 H 0.2524 0.5430 0.7959 0.093 Uiso 1 1 calc R . . C2 C 0.2507(5) 0.4599(6) 0.7267(9) 0.091(4) Uani 1 1 d . . . H2A H 0.2720 0.4755 0.6618 0.109 Uiso 1 1 calc R . . H2B H 0.2065 0.4582 0.7096 0.109 Uiso 1 1 calc R . . C3 C 0.2738(6) 0.3971(6) 0.7488(9) 0.088(4) Uani 1 1 d . . . H3 H 0.2727 0.3747 0.6787 0.105 Uiso 1 1 calc R . . C4 C 0.3403(6) 0.3981(6) 0.7907(11) 0.099(5) Uani 1 1 d . . . H4A H 0.3519 0.3578 0.8119 0.119 Uiso 1 1 calc R . . H4B H 0.3673 0.4100 0.7299 0.119 Uiso 1 1 calc R . . C5 C 0.3521(5) 0.4382(7) 0.8862(13) 0.096(5) Uani 1 1 d . . . H5 H 0.3973 0.4418 0.8954 0.115 Uiso 1 1 calc R . . C6 C 0.3266(6) 0.4991(6) 0.8632(10) 0.092(4) Uani 1 1 d . . . H6A H 0.3532 0.5181 0.8084 0.111 Uiso 1 1 calc R . . H6B H 0.3295 0.5223 0.9310 0.111 Uiso 1 1 calc R . . C7 C 0.1745(6) 0.5252(5) 0.9274(10) 0.072(4) Uani 1 1 d . . . H7 H 0.1723 0.5602 0.8856 0.086 Uiso 1 1 calc R . . C8 C 0.1292(5) 0.5129(4) 1.0106(9) 0.063(3) Uani 1 1 d . . . H8 H 0.1330 0.4783 1.0530 0.076 Uiso 1 1 calc R . . C9 C 0.0810(5) 0.5501(5) 1.0296(9) 0.063(3) Uani 1 1 d . . . H9 H 0.0800 0.5860 0.9904 0.076 Uiso 1 1 calc R . . C10 C 0.0309(5) 0.5382(7) 1.1066(9) 0.062(3) Uani 1 1 d . . . C11 C -0.0149(8) 0.5816(6) 1.1136(10) 0.096(5) Uani 1 1 d . . . H11 H -0.0127 0.6156 1.0690 0.115 Uiso 1 1 calc R . . C12 C -0.0626(8) 0.5746(8) 1.1848(16) 0.123(6) Uani 1 1 d . . . H12 H -0.0937 0.6035 1.1897 0.147 Uiso 1 1 calc R . . C13 C -0.0651(7) 0.5258(10) 1.2484(13) 0.117(6) Uani 1 1 d . . . H13 H -0.0983 0.5206 1.2974 0.141 Uiso 1 1 calc R . . C14 C -0.0184(8) 0.4821(7) 1.2423(13) 0.108(5) Uani 1 1 d . . . H14 H -0.0199 0.4477 1.2858 0.129 Uiso 1 1 calc R . . C15 C 0.0280(7) 0.4919(7) 1.1721(12) 0.082(4) Uani 1 1 d . . . H15 H 0.0603 0.4642 1.1693 0.098 Uiso 1 1 calc R . . C16 C 0.2050(6) 0.3214(7) 0.7992(11) 0.088(4) Uani 1 1 d . . . H16 H 0.2100 0.3077 0.7266 0.105 Uiso 1 1 calc R . . C17 C 0.1653(5) 0.2884(6) 0.8721(10) 0.076(4) Uani 1 1 d . . . H17 H 0.1577 0.3045 0.9421 0.091 Uiso 1 1 calc R . . C18 C 0.1388(6) 0.2374(7) 0.8484(11) 0.087(4) Uani 1 1 d . . . H18 H 0.1451 0.2231 0.7765 0.105 Uiso 1 1 calc R . . C19 C 0.1018(6) 0.2012(7) 0.9188(12) 0.080(4) Uani 1 1 d . . . C20 C 0.0836(7) 0.1455(7) 0.8918(13) 0.103(5) Uani 1 1 d . . . H20 H 0.0946 0.1294 0.8232 0.124 Uiso 1 1 calc R . . C21 C 0.0495(7) 0.1134(7) 0.9636(16) 0.114(6) Uani 1 1 d . . . H21 H 0.0377 0.0746 0.9447 0.137 Uiso 1 1 calc R . . C22 C 0.0320(7) 0.1358(9) 1.0619(15) 0.113(6) Uani 1 1 d . . . H22 H 0.0077 0.1128 1.1097 0.135 Uiso 1 1 calc R . . C23 C 0.0493(7) 0.1914(8) 1.0927(12) 0.110(5) Uani 1 1 d . . . H23 H 0.0371 0.2067 1.1613 0.132 Uiso 1 1 calc R . . C24 C 0.0839(6) 0.2240(5) 1.0243(15) 0.096(4) Uani 1 1 d . . . H24 H 0.0965 0.2621 1.0455 0.115 Uiso 1 1 calc R . . C25 C 0.3638(6) 0.3936(5) 1.0577(13) 0.086(4) Uani 1 1 d . . . H25 H 0.4063 0.3949 1.0414 0.103 Uiso 1 1 calc R . . C26 C 0.3452(6) 0.3691(5) 1.1606(10) 0.069(4) Uani 1 1 d . . . H26 H 0.3031 0.3705 1.1797 0.082 Uiso 1 1 calc R . . C27 C 0.3844(6) 0.3444(5) 1.2303(12) 0.081(4) Uani 1 1 d . . . H27 H 0.4266 0.3443 1.2118 0.097 Uiso 1 1 calc R . . C28 C 0.3663(9) 0.3181(6) 1.3320(13) 0.088(4) Uani 1 1 d . . . C29 C 0.4128(9) 0.2996(7) 1.3934(16) 0.131(6) Uani 1 1 d . . . H29 H 0.4532 0.3048 1.3668 0.157 Uiso 1 1 calc R . . C30 C 0.4049(10) 0.2735(10) 1.494(2) 0.171(10) Uani 1 1 d . . . H30 H 0.4388 0.2579 1.5327 0.205 Uiso 1 1 calc R . . C31 C 0.3474(13) 0.2704(7) 1.5359(15) 0.148(8) Uani 1 1 d . . . H31 H 0.3412 0.2558 1.6075 0.178 Uiso 1 1 calc R . . C32 C 0.2968(7) 0.2892(6) 1.4722(16) 0.104(5) Uani 1 1 d . . . H32 H 0.2563 0.2854 1.4994 0.125 Uiso 1 1 calc R . . C33 C 0.3070(8) 0.3129(6) 1.3712(14) 0.103(5) Uani 1 1 d . . . H33 H 0.2735 0.3259 1.3281 0.124 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 0.0718(9) 0.0812(10) 0.0686(9) 0.0123(9) 0.0139(8) -0.0017(10) Cl1 0.0712(18) 0.0623(19) 0.0440(15) 0.0058(15) 0.0173(14) -0.0056(17) N1 0.055(8) 0.090(9) 0.073(7) 0.006(6) 0.009(6) -0.006(6) N2 0.073(7) 0.095(8) 0.062(7) 0.010(6) 0.021(6) -0.001(7) N3 0.070(7) 0.080(7) 0.070(7) 0.023(6) 0.029(6) 0.003(6) C1 0.077(12) 0.075(9) 0.080(9) 0.031(8) 0.013(9) -0.009(8) C2 0.080(11) 0.114(12) 0.078(9) 0.030(9) 0.024(7) -0.008(9) C3 0.099(11) 0.114(14) 0.050(7) -0.001(8) 0.038(9) -0.009(10) C4 0.078(11) 0.115(14) 0.105(12) 0.043(10) 0.049(9) 0.011(9) C5 0.046(8) 0.107(14) 0.133(15) 0.009(12) 0.012(10) 0.002(9) C6 0.056(9) 0.109(13) 0.112(11) 0.016(10) 0.019(9) -0.024(9) C7 0.062(9) 0.065(10) 0.088(9) 0.009(8) -0.010(8) -0.001(8) C8 0.063(8) 0.053(8) 0.074(9) 0.005(7) -0.004(8) -0.010(7) C9 0.080(9) 0.058(8) 0.053(7) 0.000(7) -0.019(8) 0.002(7) C10 0.048(9) 0.100(12) 0.037(8) -0.018(8) -0.007(7) 0.008(9) C11 0.095(11) 0.110(13) 0.084(10) -0.019(9) 0.010(9) 0.014(11) C12 0.097(15) 0.15(2) 0.121(15) -0.039(13) -0.014(13) 0.031(14) C13 0.075(13) 0.20(2) 0.079(12) -0.032(14) 0.006(10) -0.037(15) C14 0.069(12) 0.148(15) 0.106(12) -0.005(12) -0.005(10) 0.001(13) C15 0.067(11) 0.116(14) 0.062(9) 0.017(9) -0.017(9) 0.002(9) C16 0.077(10) 0.114(13) 0.072(10) 0.002(10) 0.009(8) -0.001(10) C17 0.064(9) 0.097(12) 0.067(9) 0.010(9) 0.002(8) 0.018(9) C18 0.096(11) 0.087(12) 0.079(11) -0.028(10) 0.010(9) -0.013(9) C19 0.091(11) 0.088(13) 0.061(10) -0.001(10) -0.007(9) 0.022(10) C20 0.136(14) 0.061(12) 0.113(14) -0.028(10) -0.041(11) -0.008(10) C21 0.117(14) 0.102(15) 0.124(15) 0.017(14) -0.053(12) -0.046(11) C22 0.088(11) 0.148(19) 0.103(14) 0.035(12) -0.006(11) -0.030(12) C23 0.114(13) 0.118(15) 0.098(12) 0.014(12) 0.005(10) -0.035(11) C24 0.101(11) 0.053(10) 0.133(14) -0.002(11) -0.001(11) -0.020(8) C25 0.070(9) 0.080(11) 0.107(12) -0.006(9) -0.004(9) 0.019(8) C26 0.076(10) 0.060(9) 0.070(9) -0.007(7) 0.006(8) -0.002(8) C27 0.068(10) 0.083(10) 0.091(10) 0.006(9) -0.010(9) 0.010(8) C28 0.124(15) 0.067(10) 0.072(11) 0.004(8) -0.035(13) 0.020(11) C29 0.159(17) 0.131(15) 0.103(14) 0.028(12) -0.034(14) 0.016(13) C30 0.17(2) 0.17(2) 0.17(3) -0.023(18) -0.06(2) 0.089(18) C31 0.27(3) 0.097(13) 0.079(14) 0.017(10) -0.069(19) 0.042(18) C32 0.151(16) 0.083(11) 0.080(10) -0.019(10) 0.012(13) -0.044(10) C33 0.115(15) 0.115(13) 0.080(13) -0.023(11) 0.000(11) -0.015(11) _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 2.077(9) . ? Cu1 N1 2.077(10) . ? Cu1 N2 2.086(9) . ? Cu1 Cl1 2.285(3) . ? N1 C7 1.256(11) . ? N1 C1 1.482(12) . ? N2 C16 1.272(13) . ? N2 C3 1.474(12) . ? N3 C25 1.264(12) . ? N3 C5 1.475(14) . ? C1 C6 1.533(13) . ? C1 C2 1.535(14) . ? C2 C3 1.545(14) . ? C3 C4 1.542(15) . ? C4 C5 1.509(15) . ? C5 C6 1.524(15) . ? C7 C8 1.450(14) . ? C8 C9 1.373(12) . ? C9 C10 1.473(14) . ? C10 C15 1.330(14) . ? C10 C11 1.412(15) . ? C11 C12 1.370(17) . ? C12 C13 1.362(18) . ? C13 C14 1.430(18) . ? C14 C15 1.349(15) . ? C16 C17 1.457(15) . ? C17 C18 1.333(13) . ? C18 C19 1.444(15) . ? C19 C20 1.373(15) . ? C19 C24 1.448(15) . ? C20 C21 1.369(17) . ? C21 C22 1.365(17) . ? C22 C23 1.378(17) . ? C23 C24 1.353(15) . ? C25 C26 1.441(15) . ? C26 C27 1.335(13) . ? C27 C28 1.441(16) . ? C28 C29 1.334(17) . ? C28 C33 1.389(16) . ? C29 C30 1.38(2) . ? C30 C31 1.36(2) . ? C31 C32 1.422(18) . ? C32 C33 1.371(16) . ? 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 N1 96.8(4) . . ? N3 Cu1 N2 93.1(4) . . ? N1 Cu1 N2 91.4(4) . . ? N3 Cu1 Cl1 120.6(3) . . ? N1 Cu1 Cl1 122.8(3) . . ? N2 Cu1 Cl1 124.3(3) . . ? C7 N1 C1 117.1(11) . . ? C7 N1 Cu1 130.2(9) . . ? C1 N1 Cu1 112.4(7) . . ? C16 N2 C3 119.5(11) . . ? C16 N2 Cu1 127.0(9) . . ? C3 N2 Cu1 113.5(8) . . ? C25 N3 C5 118.1(11) . . ? C25 N3 Cu1 130.0(9) . . ? C5 N3 Cu1 111.3(8) . . ? N1 C1 C6 110.8(9) . . ? N1 C1 C2 110.2(10) . . ? C6 C1 C2 110.5(10) . . ? C1 C2 C3 114.0(10) . . ? N2 C3 C4 110.7(10) . . ? N2 C3 C2 110.0(10) . . ? C4 C3 C2 110.7(11) . . ? C5 C4 C3 115.4(11) . . ? N3 C5 C4 111.1(11) . . ? N3 C5 C6 111.6(11) . . ? C4 C5 C6 110.3(12) . . ? C5 C6 C1 116.7(10) . . ? N1 C7 C8 119.1(11) . . ? C9 C8 C7 121.7(11) . . ? C8 C9 C10 124.5(11) . . ? C15 C10 C11 119.2(13) . . ? C15 C10 C9 124.7(15) . . ? C11 C10 C9 115.9(15) . . ? C12 C11 C10 119.7(15) . . ? C13 C12 C11 119.5(18) . . ? C12 C13 C14 120.8(18) . . ? C15 C14 C13 117.1(17) . . ? C10 C15 C14 123.6(15) . . ? N2 C16 C17 123.5(13) . . ? C18 C17 C16 125.4(13) . . ? C17 C18 C19 127.9(13) . . ? C20 C19 C18 123.2(17) . . ? C20 C19 C24 118.1(14) . . ? C18 C19 C24 118.7(16) . . ? C21 C20 C19 120.0(15) . . ? C22 C21 C20 121.3(17) . . ? C21 C22 C23 120.8(16) . . ? C24 C23 C22 119.3(16) . . ? C23 C24 C19 120.5(14) . . ? N3 C25 C26 123.6(12) . . ? C27 C26 C25 122.9(13) . . ? C26 C27 C28 123.6(13) . . ? C29 C28 C33 119.4(16) . . ? C29 C28 C27 114.3(19) . . ? C33 C28 C27 126.3(16) . . ? C28 C29 C30 123(2) . . ? C31 C30 C29 118(2) . . ? C30 C31 C32 120(2) . . ? C33 C32 C31 119.3(16) . . ? C32 C33 C28 119.9(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Cu1 N1 C7 -143.2(11) . . . . ? N2 Cu1 N1 C7 123.5(11) . . . . ? Cl1 Cu1 N1 C7 -9.9(12) . . . . ? N3 Cu1 N1 C1 43.2(8) . . . . ? N2 Cu1 N1 C1 -50.1(8) . . . . ? Cl1 Cu1 N1 C1 176.5(7) . . . . ? N3 Cu1 N2 C16 130.7(12) . . . . ? N1 Cu1 N2 C16 -132.5(12) . . . . ? Cl1 Cu1 N2 C16 -0.2(13) . . . . ? N3 Cu1 N2 C3 -47.1(9) . . . . ? N1 Cu1 N2 C3 49.8(9) . . . . ? Cl1 Cu1 N2 C3 -177.9(7) . . . . ? N1 Cu1 N3 C25 145.7(11) . . . . ? N2 Cu1 N3 C25 -122.5(11) . . . . ? Cl1 Cu1 N3 C25 11.0(12) . . . . ? N1 Cu1 N3 C5 -43.5(9) . . . . ? N2 Cu1 N3 C5 48.3(9) . . . . ? Cl1 Cu1 N3 C5 -178.2(8) . . . . ? C7 N1 C1 C6 128.1(11) . . . . ? Cu1 N1 C1 C6 -57.4(11) . . . . ? C7 N1 C1 C2 -109.3(12) . . . . ? Cu1 N1 C1 C2 65.2(11) . . . . ? N1 C1 C2 C3 -73.2(12) . . . . ? C6 C1 C2 C3 49.7(13) . . . . ? C16 N2 C3 C4 -118.5(13) . . . . ? Cu1 N2 C3 C4 59.5(13) . . . . ? C16 N2 C3 C2 118.8(13) . . . . ? Cu1 N2 C3 C2 -63.3(12) . . . . ? C1 C2 C3 N2 71.8(13) . . . . ? C1 C2 C3 C4 -51.0(13) . . . . ? N2 C3 C4 C5 -70.6(15) . . . . ? C2 C3 C4 C5 51.8(13) . . . . ? C25 N3 C5 C4 107.6(13) . . . . ? Cu1 N3 C5 C4 -64.5(12) . . . . ? C25 N3 C5 C6 -128.8(12) . . . . ? Cu1 N3 C5 C6 59.1(13) . . . . ? C3 C4 C5 N3 74.1(14) . . . . ? C3 C4 C5 C6 -50.2(14) . . . . ? N3 C5 C6 C1 -74.4(15) . . . . ? C4 C5 C6 C1 49.7(15) . . . . ? N1 C1 C6 C5 72.7(14) . . . . ? C2 C1 C6 C5 -49.7(14) . . . . ? C1 N1 C7 C8 177.4(9) . . . . ? Cu1 N1 C7 C8 4.0(16) . . . . ? N1 C7 C8 C9 -178.1(10) . . . . ? C7 C8 C9 C10 175.1(9) . . . . ? C8 C9 C10 C15 4.4(17) . . . . ? C8 C9 C10 C11 -179.2(10) . . . . ? C15 C10 C11 C12 -2.2(18) . . . . ? C9 C10 C11 C12 -178.7(11) . . . . ? C10 C11 C12 C13 0(2) . . . . ? C11 C12 C13 C14 0(2) . . . . ? C12 C13 C14 C15 1(2) . . . . ? C11 C10 C15 C14 3.5(19) . . . . ? C9 C10 C15 C14 179.7(11) . . . . ? C13 C14 C15 C10 -3(2) . . . . ? C3 N2 C16 C17 178.4(11) . . . . ? Cu1 N2 C16 C17 0.7(19) . . . . ? N2 C16 C17 C18 -174.3(13) . . . . ? C16 C17 C18 C19 176.5(11) . . . . ? C17 C18 C19 C20 -170.7(13) . . . . ? C17 C18 C19 C24 8.1(19) . . . . ? C18 C19 C20 C21 178.7(12) . . . . ? C24 C19 C20 C21 -0.1(19) . . . . ? C19 C20 C21 C22 1(2) . . . . ? C20 C21 C22 C23 -1(2) . . . . ? C21 C22 C23 C24 0(2) . . . . ? C22 C23 C24 C19 1(2) . . . . ? C20 C19 C24 C23 -1.1(19) . . . . ? C18 C19 C24 C23 -179.9(12) . . . . ? C5 N3 C25 C26 179.2(11) . . . . ? Cu1 N3 C25 C26 -10.5(18) . . . . ? N3 C25 C26 C27 175.1(12) . . . . ? C25 C26 C27 C28 -178.0(11) . . . . ? C26 C27 C28 C29 -175.5(13) . . . . ? C26 C27 C28 C33 2(2) . . . . ? C33 C28 C29 C30 2(3) . . . . ? C27 C28 C29 C30 179.7(16) . . . . ? C28 C29 C30 C31 -5(3) . . . . ? C29 C30 C31 C32 6(3) . . . . ? C30 C31 C32 C33 -3(3) . . . . ? C31 C32 C33 C28 0(2) . . . . ? C29 C28 C33 C32 0(2) . . . . ? C27 C28 C33 C32 -176.9(12) . . . . ? _diffrn_measured_fraction_theta_max 0.790 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.790 _refine_diff_density_max 0.355 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.064 data_phw0508a _database_code_depnum_ccdc_archive 'CCDC 279582' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H33 Br Cu N3' _chemical_formula_sum 'C33 H33 Br Cu N3' _chemical_formula_weight 615.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 12.957(3) _cell_length_b 21.405(5) _cell_length_c 21.458(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5951(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5633 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 28.28 _exptl_crystal_description blocks _exptl_crystal_colour red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 2.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.799 _exptl_absorpt_correction_T_max 0.940 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 60979 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_sigmaI/netI 0.0658 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 0.95 _diffrn_reflns_theta_max 28.33 _reflns_number_total 14757 _reflns_number_gt 11925 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0240P)^2^+2.5030P] 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 0.000(8) _refine_ls_number_reflns 14757 _refine_ls_number_parameters 686 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.0773 _refine_ls_wR_factor_gt 0.0684 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Br1 Br 0.56409(2) 0.875778(15) 0.830729(17) 0.01930(8) Uani 1 1 d . . . Br2 Br 0.47216(3) 0.614804(17) 0.492474(17) 0.02328(8) Uani 1 1 d . . . C1 C 0.1820(3) 0.83869(17) 0.89443(18) 0.0223(8) Uani 1 1 d . . . H1 H 0.1163 0.8628 0.8901 0.027 Uiso 1 1 calc R . . C2 C 0.2024(3) 0.82878(18) 0.96375(18) 0.0257(9) Uani 1 1 d . . . H2A H 0.1382 0.8134 0.9835 0.031 Uiso 1 1 calc R . . H2B H 0.2193 0.8696 0.9828 0.031 Uiso 1 1 calc R . . C3 C 0.2901(3) 0.78255(18) 0.97864(18) 0.0247(9) Uani 1 1 d . . . H3 H 0.2881 0.7730 1.0242 0.030 Uiso 1 1 calc R . . C4 C 0.2759(3) 0.72155(16) 0.94278(19) 0.0263(9) Uani 1 1 d . . . H4A H 0.2177 0.6983 0.9617 0.032 Uiso 1 1 calc R . . H4B H 0.3388 0.6959 0.9481 0.032 Uiso 1 1 calc R . . C5 C 0.2547(3) 0.72860(16) 0.87287(19) 0.0240(8) Uani 1 1 d . . . H5 H 0.2318 0.6872 0.8563 0.029 Uiso 1 1 calc R . . C6 C 0.1684(3) 0.77616(16) 0.86119(19) 0.0234(8) Uani 1 1 d . . . H6A H 0.1637 0.7840 0.8158 0.028 Uiso 1 1 calc R . . H6B H 0.1021 0.7575 0.8746 0.028 Uiso 1 1 calc R . . C7 C 0.2454(3) 0.93068(16) 0.84745(16) 0.0199(8) Uani 1 1 d . . . H7 H 0.1775 0.9467 0.8524 0.024 Uiso 1 1 calc R . . C8 C 0.3236(3) 0.96941(16) 0.81920(17) 0.0200(8) Uani 1 1 d . . . H8 H 0.3904 0.9520 0.8133 0.024 Uiso 1 1 calc R . . C9 C 0.3078(3) 1.02795(16) 0.80096(17) 0.0200(8) Uani 1 1 d . . . H9 H 0.2403 1.0444 0.8065 0.024 Uiso 1 1 calc R . . C10 C 0.3851(3) 1.06950(17) 0.77303(18) 0.0209(8) Uani 1 1 d . . . C11 C 0.3593(3) 1.13165(17) 0.76167(19) 0.0249(8) Uani 1 1 d . . . H11 H 0.2923 1.1464 0.7720 0.030 Uiso 1 1 calc R . . C12 C 0.4310(3) 1.17221(18) 0.73533(19) 0.0279(9) Uani 1 1 d . . . H12 H 0.4126 1.2145 0.7278 0.033 Uiso 1 1 calc R . . C13 C 0.5284(3) 1.15139(18) 0.72003(18) 0.0254(9) Uani 1 1 d . . . H13 H 0.5773 1.1792 0.7022 0.030 Uiso 1 1 calc R . . C14 C 0.5545(3) 1.08953(18) 0.73085(19) 0.0266(9) Uani 1 1 d . . . H14 H 0.6213 1.0749 0.7199 0.032 Uiso 1 1 calc R . . C15 C 0.4845(3) 1.04893(17) 0.75735(18) 0.0228(8) Uani 1 1 d . . . H15 H 0.5037 1.0068 0.7650 0.027 Uiso 1 1 calc R . . C16 C 0.4459(3) 0.82874(17) 1.01048(18) 0.0227(8) Uani 1 1 d . . . H16 H 0.4239 0.8180 1.0513 0.027 Uiso 1 1 calc R . . C17 C 0.5407(3) 0.86322(16) 1.00298(19) 0.0224(8) Uani 1 1 d . . . H17 H 0.5676 0.8688 0.9622 0.027 Uiso 1 1 calc R . . C18 C 0.5925(3) 0.88786(17) 1.05147(18) 0.0235(8) Uani 1 1 d . . . H18 H 0.5676 0.8779 1.0919 0.028 Uiso 1 1 calc R . . C19 C 0.6827(3) 0.92809(16) 1.04827(18) 0.0239(9) Uani 1 1 d . . . C20 C 0.7281(3) 0.94793(18) 1.1039(2) 0.0310(9) Uani 1 1 d . . . H20 H 0.7000 0.9347 1.1426 0.037 Uiso 1 1 calc R . . C21 C 0.8136(4) 0.9866(2) 1.1032(2) 0.0441(12) Uani 1 1 d . . . H21 H 0.8444 0.9993 1.1413 0.053 Uiso 1 1 calc R . . C22 C 0.8540(3) 1.0066(2) 1.0479(3) 0.0434(12) Uani 1 1 d . . . H22 H 0.9121 1.0336 1.0477 0.052 Uiso 1 1 calc R . . C23 C 0.8106(3) 0.98761(19) 0.9921(2) 0.0400(11) Uani 1 1 d . . . H23 H 0.8393 1.0013 0.9537 0.048 Uiso 1 1 calc R . . C24 C 0.7246(3) 0.94847(17) 0.9923(2) 0.0293(9) Uani 1 1 d . . . H24 H 0.6946 0.9357 0.9539 0.035 Uiso 1 1 calc R . . C25 C 0.3849(3) 0.70987(16) 0.79854(17) 0.0200(8) Uani 1 1 d . . . H25 H 0.3503 0.6715 0.7910 0.024 Uiso 1 1 calc R . . C26 C 0.4745(3) 0.72467(16) 0.76260(17) 0.0198(8) Uani 1 1 d . . . H26 H 0.5083 0.7632 0.7708 0.024 Uiso 1 1 calc R . . C27 C 0.5135(3) 0.68795(17) 0.71836(17) 0.0203(8) Uani 1 1 d . . . H27 H 0.4808 0.6487 0.7121 0.024 Uiso 1 1 calc R . . C28 C 0.6016(3) 0.70230(17) 0.67864(17) 0.0205(8) Uani 1 1 d . . . C29 C 0.6398(3) 0.65804(19) 0.63668(19) 0.0282(9) Uani 1 1 d . . . H29 H 0.6085 0.6179 0.6347 0.034 Uiso 1 1 calc R . . C30 C 0.7219(3) 0.6714(2) 0.5981(2) 0.0354(10) Uani 1 1 d . . . H30 H 0.7460 0.6408 0.5695 0.042 Uiso 1 1 calc R . . C31 C 0.7690(3) 0.7289(2) 0.60086(18) 0.0305(10) Uani 1 1 d . . . H31 H 0.8263 0.7378 0.5748 0.037 Uiso 1 1 calc R . . C32 C 0.7327(3) 0.77357(19) 0.64164(18) 0.0274(9) Uani 1 1 d . . . H32 H 0.7649 0.8134 0.6431 0.033 Uiso 1 1 calc R . . C33 C 0.6503(3) 0.76112(17) 0.68033(17) 0.0220(8) Uani 1 1 d . . . H33 H 0.6263 0.7923 0.7083 0.026 Uiso 1 1 calc R . . C34 C 0.7824(3) 0.73759(16) 0.40304(18) 0.0206(8) Uani 1 1 d . . . H34 H 0.8103 0.7809 0.4080 0.025 Uiso 1 1 calc R . . C35 C 0.7550(3) 0.72811(15) 0.33527(19) 0.0213(8) Uani 1 1 d . . . H35A H 0.8131 0.7434 0.3095 0.026 Uiso 1 1 calc R . . H35B H 0.6942 0.7544 0.3255 0.026 Uiso 1 1 calc R . . C36 C 0.7307(3) 0.66025(16) 0.31569(17) 0.0212(8) Uani 1 1 d . . . H36 H 0.7277 0.6584 0.2692 0.025 Uiso 1 1 calc R . . C37 C 0.8153(3) 0.61582(15) 0.33808(18) 0.0210(8) Uani 1 1 d . . . H37A H 0.8776 0.6226 0.3122 0.025 Uiso 1 1 calc R . . H37B H 0.7919 0.5724 0.3310 0.025 Uiso 1 1 calc R . . C38 C 0.8454(3) 0.62287(16) 0.40677(18) 0.0216(8) Uani 1 1 d . . . H38 H 0.9100 0.5984 0.4140 0.026 Uiso 1 1 calc R . . C39 C 0.8669(3) 0.69093(16) 0.42350(18) 0.0222(8) Uani 1 1 d . . . H39A H 0.9330 0.7035 0.4041 0.027 Uiso 1 1 calc R . . H39B H 0.8755 0.6940 0.4692 0.027 Uiso 1 1 calc R . . C40 C 0.6588(3) 0.78060(17) 0.47102(16) 0.0198(8) Uani 1 1 d . . . H40 H 0.6954 0.8185 0.4646 0.024 Uiso 1 1 calc R . . C41 C 0.5719(3) 0.78143(16) 0.51214(16) 0.0197(8) Uani 1 1 d . . . H41 H 0.5322 0.7444 0.5167 0.024 Uiso 1 1 calc R . . C42 C 0.5442(3) 0.83213(18) 0.54429(17) 0.0221(8) Uani 1 1 d . . . H42 H 0.5813 0.8694 0.5357 0.027 Uiso 1 1 calc R . . C43 C 0.4624(3) 0.83642(18) 0.59165(17) 0.0230(8) Uani 1 1 d . . . C44 C 0.4449(3) 0.8935(2) 0.6213(2) 0.0326(10) Uani 1 1 d . . . H44 H 0.4827 0.9294 0.6090 0.039 Uiso 1 1 calc R . . C45 C 0.3729(3) 0.8978(2) 0.6687(2) 0.0391(11) Uani 1 1 d . . . H45 H 0.3617 0.9368 0.6887 0.047 Uiso 1 1 calc R . . C46 C 0.3177(3) 0.8466(2) 0.68689(19) 0.0344(11) Uani 1 1 d . . . H46 H 0.2698 0.8498 0.7202 0.041 Uiso 1 1 calc R . . C47 C 0.3318(3) 0.7901(2) 0.65664(19) 0.0309(10) Uani 1 1 d . . . H47 H 0.2919 0.7547 0.6683 0.037 Uiso 1 1 calc R . . C48 C 0.4039(3) 0.78507(18) 0.60949(17) 0.0240(8) Uani 1 1 d . . . H48 H 0.4135 0.7461 0.5891 0.029 Uiso 1 1 calc R . . C49 C 0.5604(3) 0.62653(16) 0.30093(17) 0.0217(8) Uani 1 1 d . . . H49 H 0.5777 0.6274 0.2579 0.026 Uiso 1 1 calc R . . C50 C 0.4575(3) 0.60790(15) 0.31854(19) 0.0226(8) Uani 1 1 d . . . H50 H 0.4383 0.6109 0.3612 0.027 Uiso 1 1 calc R . . C51 C 0.3879(3) 0.58654(16) 0.27773(19) 0.0229(8) Uani 1 1 d . . . H51 H 0.4084 0.5849 0.2353 0.027 Uiso 1 1 calc R . . C52 C 0.2826(3) 0.56527(16) 0.29231(19) 0.0212(8) Uani 1 1 d . . . C53 C 0.2173(3) 0.54860(18) 0.2429(2) 0.0286(9) Uani 1 1 d . . . H53 H 0.2425 0.5488 0.2013 0.034 Uiso 1 1 calc R . . C54 C 0.1156(3) 0.53172(17) 0.2549(2) 0.0320(10) Uani 1 1 d . . . H54 H 0.0714 0.5205 0.2214 0.038 Uiso 1 1 calc R . . C55 C 0.0786(3) 0.53124(17) 0.3149(2) 0.0331(11) Uani 1 1 d . . . H55 H 0.0086 0.5206 0.3227 0.040 Uiso 1 1 calc R . . C56 C 0.1434(3) 0.54630(16) 0.3640(2) 0.0280(9) Uani 1 1 d . . . H56 H 0.1178 0.5456 0.4055 0.034 Uiso 1 1 calc R . . C57 C 0.2447(3) 0.56232(16) 0.35302(19) 0.0247(9) Uani 1 1 d . . . H57 H 0.2891 0.5714 0.3871 0.030 Uiso 1 1 calc R . . C58 C 0.7844(3) 0.54666(16) 0.47682(16) 0.0200(8) Uani 1 1 d . . . H58 H 0.8524 0.5301 0.4753 0.024 Uiso 1 1 calc R . . C59 C 0.7073(3) 0.51506(16) 0.51395(16) 0.0198(8) Uani 1 1 d . . . H59 H 0.6421 0.5345 0.5197 0.024 Uiso 1 1 calc R . . C60 C 0.7243(3) 0.45988(17) 0.54039(17) 0.0233(8) Uani 1 1 d . . . H60 H 0.7925 0.4438 0.5379 0.028 Uiso 1 1 calc R . . C61 C 0.6479(3) 0.42144(17) 0.57309(18) 0.0234(8) Uani 1 1 d . . . C62 C 0.6753(3) 0.36157(17) 0.59359(19) 0.0275(9) Uani 1 1 d . . . H62 H 0.7442 0.3474 0.5883 0.033 Uiso 1 1 calc R . . C63 C 0.6033(3) 0.32276(18) 0.6214(2) 0.0338(10) Uani 1 1 d . . . H63 H 0.6228 0.2821 0.6346 0.041 Uiso 1 1 calc R . . C64 C 0.5036(3) 0.34296(19) 0.63012(19) 0.0329(10) Uani 1 1 d . . . H64 H 0.4543 0.3162 0.6492 0.040 Uiso 1 1 calc R . . C65 C 0.4751(3) 0.4025(2) 0.6110(2) 0.0346(10) Uani 1 1 d . . . H65 H 0.4064 0.4165 0.6174 0.042 Uiso 1 1 calc R . . C66 C 0.5465(3) 0.44143(18) 0.58282(18) 0.0262(9) Uani 1 1 d . . . H66 H 0.5263 0.4821 0.5699 0.031 Uiso 1 1 calc R . . Cu1 Cu 0.40738(3) 0.830560(19) 0.87063(2) 0.01857(9) Uani 1 1 d . . . Cu2 Cu 0.62545(3) 0.644284(19) 0.43659(2) 0.01858(9) Uani 1 1 d . . . N1 N 0.2657(2) 0.87543(13) 0.86581(14) 0.0196(6) Uani 1 1 d . . . N2 N 0.3904(2) 0.81222(14) 0.96427(14) 0.0203(7) Uani 1 1 d . . . N3 N 0.3498(2) 0.74659(13) 0.84048(15) 0.0202(7) Uani 1 1 d . . . N4 N 0.6899(2) 0.73167(13) 0.44251(14) 0.0186(6) Uani 1 1 d . . . N5 N 0.6290(2) 0.64196(13) 0.34063(14) 0.0188(6) Uani 1 1 d . . . N6 N 0.7637(2) 0.59622(13) 0.44594(14) 0.0191(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01227(16) 0.01684(16) 0.02879(19) 0.00344(16) 0.00325(15) -0.00122(13) Br2 0.01336(17) 0.02664(18) 0.0298(2) 0.00479(17) 0.00546(16) -0.00165(14) C1 0.0105(17) 0.0257(19) 0.031(2) 0.0047(16) 0.0045(15) 0.0008(14) C2 0.0146(18) 0.031(2) 0.031(2) 0.0000(18) 0.0057(16) -0.0037(16) C3 0.0188(19) 0.033(2) 0.023(2) 0.0080(17) 0.0058(15) -0.0085(16) C4 0.0168(18) 0.0233(19) 0.039(2) 0.0102(19) 0.0065(17) -0.0061(14) C5 0.0203(18) 0.0203(19) 0.031(2) 0.0034(17) 0.0004(17) -0.0055(14) C6 0.0138(17) 0.026(2) 0.031(2) 0.0034(17) 0.0005(16) -0.0058(14) C7 0.0128(17) 0.0225(19) 0.024(2) -0.0047(15) 0.0017(14) 0.0013(14) C8 0.0180(18) 0.0192(18) 0.023(2) -0.0003(15) 0.0046(15) 0.0020(13) C9 0.0169(19) 0.0194(18) 0.024(2) -0.0017(16) 0.0033(15) 0.0027(14) C10 0.0195(19) 0.0199(19) 0.023(2) -0.0027(15) -0.0010(15) 0.0029(15) C11 0.023(2) 0.019(2) 0.033(2) 0.0015(16) -0.0003(17) 0.0051(15) C12 0.031(2) 0.0186(19) 0.034(2) 0.0018(17) -0.0027(18) -0.0002(17) C13 0.026(2) 0.026(2) 0.024(2) -0.0005(17) -0.0008(17) -0.0090(17) C14 0.024(2) 0.029(2) 0.027(2) -0.0005(18) 0.0020(17) -0.0012(17) C15 0.022(2) 0.0170(18) 0.030(2) -0.0012(16) 0.0003(17) 0.0017(15) C16 0.0217(19) 0.0232(19) 0.023(2) 0.0041(15) 0.0056(15) 0.0040(15) C17 0.0184(18) 0.0246(19) 0.024(2) 0.0005(16) 0.0006(16) -0.0003(14) C18 0.0224(19) 0.024(2) 0.024(2) 0.0020(16) -0.0001(16) 0.0043(15) C19 0.023(2) 0.0159(18) 0.033(2) -0.0035(16) -0.0040(17) 0.0067(15) C20 0.031(2) 0.032(2) 0.030(2) -0.0096(18) -0.0032(18) 0.0010(18) C21 0.042(3) 0.041(3) 0.050(3) -0.019(2) -0.013(2) -0.004(2) C22 0.027(2) 0.027(2) 0.076(4) 0.003(2) -0.012(2) -0.0081(18) C23 0.032(2) 0.034(2) 0.054(3) 0.017(2) -0.008(2) -0.0086(18) C24 0.027(2) 0.028(2) 0.033(2) 0.0084(19) -0.010(2) -0.0034(16) C25 0.021(2) 0.0143(17) 0.025(2) 0.0029(15) -0.0053(16) -0.0006(14) C26 0.0142(17) 0.0184(18) 0.027(2) 0.0034(16) -0.0022(15) 0.0016(14) C27 0.0187(19) 0.0172(18) 0.025(2) 0.0014(15) -0.0087(16) 0.0019(14) C28 0.0190(18) 0.0228(19) 0.0197(19) -0.0019(15) -0.0070(15) 0.0074(15) C29 0.023(2) 0.030(2) 0.032(2) -0.0078(18) -0.0066(17) 0.0037(17) C30 0.028(2) 0.050(3) 0.028(2) -0.015(2) -0.0019(18) 0.014(2) C31 0.017(2) 0.049(3) 0.025(2) -0.0005(19) -0.0022(16) 0.0030(18) C32 0.022(2) 0.038(2) 0.023(2) 0.0027(18) 0.0010(16) -0.0012(17) C33 0.024(2) 0.026(2) 0.0161(19) 0.0000(15) 0.0001(15) 0.0036(16) C34 0.0182(18) 0.0164(18) 0.027(2) -0.0014(16) 0.0073(16) -0.0042(14) C35 0.0224(18) 0.0170(17) 0.024(2) 0.0001(16) 0.0085(17) -0.0033(14) C36 0.0201(19) 0.0214(18) 0.022(2) 0.0004(15) 0.0089(15) -0.0023(14) C37 0.0192(17) 0.0155(17) 0.028(2) -0.0026(16) 0.0092(16) -0.0023(13) C38 0.0140(17) 0.0208(18) 0.030(2) 0.0046(16) 0.0071(15) 0.0013(14) C39 0.0150(17) 0.0261(19) 0.026(2) -0.0012(15) 0.0048(16) -0.0046(15) C40 0.0168(18) 0.0194(18) 0.023(2) -0.0012(15) -0.0001(15) -0.0002(14) C41 0.0153(18) 0.0222(18) 0.0218(19) -0.0010(15) -0.0002(15) 0.0010(14) C42 0.0188(19) 0.0244(19) 0.023(2) -0.0021(16) -0.0019(15) 0.0038(15) C43 0.0158(18) 0.033(2) 0.021(2) -0.0040(16) -0.0039(15) 0.0080(15) C44 0.027(2) 0.032(2) 0.040(3) -0.0114(19) 0.0037(19) 0.0053(17) C45 0.040(3) 0.043(3) 0.035(3) -0.015(2) 0.005(2) 0.013(2) C46 0.028(2) 0.055(3) 0.021(2) -0.001(2) 0.0038(18) 0.020(2) C47 0.022(2) 0.042(3) 0.029(2) 0.0072(19) 0.0008(18) 0.0085(18) C48 0.0186(19) 0.033(2) 0.021(2) 0.0019(16) -0.0008(16) 0.0097(16) C49 0.0245(19) 0.0195(18) 0.0211(19) 0.0040(15) 0.0060(16) 0.0030(15) C50 0.023(2) 0.0154(17) 0.029(2) -0.0005(16) -0.0014(16) 0.0016(13) C51 0.021(2) 0.0194(19) 0.028(2) -0.0007(16) 0.0003(16) 0.0051(15) C52 0.023(2) 0.0091(17) 0.032(2) -0.0003(15) -0.0022(16) 0.0028(14) C53 0.029(2) 0.021(2) 0.036(2) -0.0044(17) -0.0064(19) 0.0029(16) C54 0.028(2) 0.018(2) 0.050(3) -0.0063(18) -0.015(2) -0.0002(16) C55 0.020(2) 0.0188(19) 0.060(3) 0.0050(19) -0.002(2) -0.0025(15) C56 0.024(2) 0.0200(19) 0.040(2) 0.0073(18) 0.0025(19) 0.0018(15) C57 0.025(2) 0.0146(18) 0.035(2) 0.0055(15) -0.0074(17) 0.0000(15) C58 0.0154(18) 0.0206(18) 0.024(2) -0.0006(15) 0.0045(14) 0.0013(14) C59 0.0138(18) 0.023(2) 0.023(2) -0.0027(15) 0.0052(15) 0.0020(14) C60 0.022(2) 0.025(2) 0.022(2) 0.0017(16) 0.0040(16) 0.0041(16) C61 0.028(2) 0.023(2) 0.020(2) -0.0013(16) 0.0030(16) -0.0011(15) C62 0.033(2) 0.023(2) 0.027(2) -0.0006(17) 0.0049(18) 0.0048(16) C63 0.047(3) 0.018(2) 0.036(2) 0.0023(17) 0.006(2) -0.0050(19) C64 0.043(3) 0.033(2) 0.023(2) 0.0045(18) 0.0035(19) -0.017(2) C65 0.025(2) 0.049(3) 0.029(2) 0.003(2) 0.0066(19) -0.0052(19) C66 0.023(2) 0.026(2) 0.030(2) 0.0057(17) 0.0010(17) -0.0010(16) Cu1 0.0136(2) 0.0170(2) 0.0251(2) 0.00262(19) 0.00276(18) -0.00202(16) Cu2 0.0137(2) 0.0173(2) 0.0247(2) 0.00084(19) 0.00485(19) -0.00105(17) N1 0.0163(15) 0.0235(16) 0.0191(15) -0.0002(14) 0.0012(13) -0.0010(12) N2 0.0126(15) 0.0241(16) 0.0241(17) 0.0041(13) 0.0016(13) -0.0029(12) N3 0.0158(15) 0.0168(15) 0.0280(18) 0.0041(13) 0.0005(13) -0.0022(11) N4 0.0177(15) 0.0173(15) 0.0207(16) -0.0004(13) 0.0025(13) -0.0018(11) N5 0.0172(15) 0.0177(15) 0.0216(16) 0.0009(13) 0.0012(13) -0.0001(11) N6 0.0145(15) 0.0206(15) 0.0221(17) 0.0010(13) 0.0040(12) -0.0008(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 Br1 Cu1 2.4068(7) . ? Br2 Cu2 2.4044(7) . ? C1 N1 1.474(4) . ? C1 C2 1.526(5) . ? C1 C6 1.527(5) . ? C1 H1 1.0000 . ? C2 C3 1.541(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N2 1.479(4) . ? C3 C4 1.527(5) . ? C3 H3 1.0000 . ? C4 C5 1.532(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N3 1.466(4) . ? C5 C6 1.534(5) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N1 1.274(4) . ? C7 C8 1.443(5) . ? C7 H7 0.9500 . ? C8 C9 1.329(5) . ? C8 H8 0.9500 . ? C9 C10 1.467(5) . ? C9 H9 0.9500 . ? C10 C11 1.393(5) . ? C10 C15 1.402(5) . ? C11 C12 1.391(5) . ? C11 H11 0.9500 . ? C12 C13 1.379(5) . ? C12 H12 0.9500 . ? C13 C14 1.386(6) . ? C13 H13 0.9500 . ? C14 C15 1.379(5) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 N2 1.274(5) . ? C16 C17 1.442(5) . ? C16 H16 0.9500 . ? C17 C18 1.346(5) . ? C17 H17 0.9500 . ? C18 C19 1.453(5) . ? C18 H18 0.9500 . ? C19 C24 1.389(6) . ? C19 C20 1.398(5) . ? C20 C21 1.383(6) . ? C20 H20 0.9500 . ? C21 C22 1.365(7) . ? C21 H21 0.9500 . ? C22 C23 1.385(7) . ? C22 H22 0.9500 . ? C23 C24 1.393(5) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 N3 1.278(5) . ? C25 C26 1.429(5) . ? C25 H25 0.9500 . ? C26 C27 1.332(5) . ? C26 H26 0.9500 . ? C27 C28 1.458(5) . ? C27 H27 0.9500 . ? C28 C29 1.397(5) . ? C28 C33 1.409(5) . ? C29 C30 1.379(6) . ? C29 H29 0.9500 . ? C30 C31 1.375(6) . ? C30 H30 0.9500 . ? C31 C32 1.379(5) . ? C31 H31 0.9500 . ? C32 C33 1.378(5) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 N4 1.473(4) . ? C34 C35 1.511(5) . ? C34 C39 1.545(5) . ? C34 H34 1.0000 . ? C35 C36 1.544(5) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 N5 1.475(4) . ? C36 C37 1.528(5) . ? C36 H36 1.0000 . ? C37 C38 1.532(5) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 N6 1.467(4) . ? C38 C39 1.526(5) . ? C38 H38 1.0000 . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 N4 1.278(4) . ? C40 C41 1.431(5) . ? C40 H40 0.9500 . ? C41 C42 1.335(5) . ? C41 H41 0.9500 . ? C42 C43 1.471(5) . ? C42 H42 0.9500 . ? C43 C48 1.389(5) . ? C43 C44 1.396(5) . ? C44 C45 1.382(6) . ? C44 H44 0.9500 . ? C45 C46 1.366(6) . ? C45 H45 0.9500 . ? C46 C47 1.385(6) . ? C46 H46 0.9500 . ? C47 C48 1.381(5) . ? C47 H47 0.9500 . ? C48 H48 0.9500 . ? C49 N5 1.275(5) . ? C49 C50 1.441(5) . ? C49 H49 0.9500 . ? C50 C51 1.338(5) . ? C50 H50 0.9500 . ? C51 C52 1.472(5) . ? C51 H51 0.9500 . ? C52 C57 1.393(5) . ? C52 C53 1.402(5) . ? C53 C54 1.391(6) . ? C53 H53 0.9500 . ? C54 C55 1.373(6) . ? C54 H54 0.9500 . ? C55 C56 1.386(6) . ? C55 H55 0.9500 . ? C56 C57 1.377(5) . ? C56 H56 0.9500 . ? C57 H57 0.9500 . ? C58 N6 1.279(4) . ? C58 C59 1.445(5) . ? C58 H58 0.9500 . ? C59 C60 1.329(5) . ? C59 H59 0.9500 . ? C60 C61 1.466(5) . ? C60 H60 0.9500 . ? C61 C66 1.398(5) . ? C61 C62 1.400(5) . ? C62 C63 1.385(6) . ? C62 H62 0.9500 . ? C63 C64 1.374(6) . ? C63 H63 0.9500 . ? C64 C65 1.388(6) . ? C64 H64 0.9500 . ? C65 C66 1.385(5) . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? Cu1 N3 2.051(3) . ? Cu1 N2 2.059(3) . ? Cu1 N1 2.075(3) . ? Cu2 N4 2.052(3) . ? Cu2 N5 2.060(3) . ? Cu2 N6 2.075(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 110.7(3) . . ? N1 C1 C6 111.0(3) . . ? C2 C1 C6 110.7(3) . . ? N1 C1 H1 108.1 . . ? C2 C1 H1 108.1 . . ? C6 C1 H1 108.1 . . ? C1 C2 C3 114.8(3) . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? C3 C2 H2B 108.6 . . ? H2A C2 H2B 107.5 . . ? N2 C3 C4 111.6(3) . . ? N2 C3 C2 109.2(3) . . ? C4 C3 C2 110.8(3) . . ? N2 C3 H3 108.4 . . ? C4 C3 H3 108.4 . . ? C2 C3 H3 108.4 . . ? C3 C4 C5 115.5(3) . . ? C3 C4 H4A 108.4 . . ? C5 C4 H4A 108.4 . . ? C3 C4 H4B 108.4 . . ? C5 C4 H4B 108.4 . . ? H4A C4 H4B 107.5 . . ? N3 C5 C4 109.9(3) . . ? N3 C5 C6 111.2(3) . . ? C4 C5 C6 110.8(3) . . ? N3 C5 H5 108.3 . . ? C4 C5 H5 108.3 . . ? C6 C5 H5 108.3 . . ? C1 C6 C5 114.9(3) . . ? C1 C6 H6A 108.5 . . ? C5 C6 H6A 108.5 . . ? C1 C6 H6B 108.5 . . ? C5 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? N1 C7 C8 121.2(3) . . ? N1 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C9 C8 C7 123.8(3) . . ? C9 C8 H8 118.1 . . ? C7 C8 H8 118.1 . . ? C8 C9 C10 125.9(3) . . ? C8 C9 H9 117.0 . . ? C10 C9 H9 117.0 . . ? C11 C10 C15 118.6(3) . . ? C11 C10 C9 119.1(3) . . ? C15 C10 C9 122.3(3) . . ? C12 C11 C10 120.5(4) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 120.4(4) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 119.5(4) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C15 C14 C13 120.8(4) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C10 120.3(3) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? N2 C16 C17 122.4(3) . . ? N2 C16 H16 118.8 . . ? C17 C16 H16 118.8 . . ? C18 C17 C16 122.6(4) . . ? C18 C17 H17 118.7 . . ? C16 C17 H17 118.7 . . ? C17 C18 C19 126.6(4) . . ? C17 C18 H18 116.7 . . ? C19 C18 H18 116.7 . . ? C24 C19 C20 118.6(4) . . ? C24 C19 C18 122.8(3) . . ? C20 C19 C18 118.6(4) . . ? C21 C20 C19 120.7(4) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 C20 120.2(4) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 120.3(4) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C22 C23 C24 119.9(5) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C19 C24 C23 120.3(4) . . ? C19 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? N3 C25 C26 122.1(3) . . ? N3 C25 H25 118.9 . . ? C26 C25 H25 118.9 . . ? C27 C26 C25 124.2(3) . . ? C27 C26 H26 117.9 . . ? C25 C26 H26 117.9 . . ? C26 C27 C28 126.1(3) . . ? C26 C27 H27 116.9 . . ? C28 C27 H27 116.9 . . ? C29 C28 C33 117.7(4) . . ? C29 C28 C27 120.7(3) . . ? C33 C28 C27 121.6(3) . . ? C30 C29 C28 121.3(4) . . ? C30 C29 H29 119.3 . . ? C28 C29 H29 119.3 . . ? C31 C30 C29 120.1(4) . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C30 C31 C32 119.8(4) . . ? C30 C31 H31 120.1 . . ? C32 C31 H31 120.1 . . ? C33 C32 C31 120.8(4) . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.6 . . ? C32 C33 C28 120.3(4) . . ? C32 C33 H33 119.9 . . ? C28 C33 H33 119.9 . . ? N4 C34 C35 110.5(3) . . ? N4 C34 C39 110.9(3) . . ? C35 C34 C39 110.7(3) . . ? N4 C34 H34 108.2 . . ? C35 C34 H34 108.2 . . ? C39 C34 H34 108.2 . . ? C34 C35 C36 115.9(3) . . ? C34 C35 H35A 108.3 . . ? C36 C35 H35A 108.3 . . ? C34 C35 H35B 108.3 . . ? C36 C35 H35B 108.3 . . ? H35A C35 H35B 107.4 . . ? N5 C36 C37 111.2(3) . . ? N5 C36 C35 109.5(3) . . ? C37 C36 C35 110.7(3) . . ? N5 C36 H36 108.5 . . ? C37 C36 H36 108.5 . . ? C35 C36 H36 108.5 . . ? C36 C37 C38 115.1(3) . . ? C36 C37 H37A 108.5 . . ? C38 C37 H37A 108.5 . . ? C36 C37 H37B 108.5 . . ? C38 C37 H37B 108.5 . . ? H37A C37 H37B 107.5 . . ? N6 C38 C39 111.6(3) . . ? N6 C38 C37 109.2(3) . . ? C39 C38 C37 111.5(3) . . ? N6 C38 H38 108.1 . . ? C39 C38 H38 108.1 . . ? C37 C38 H38 108.1 . . ? C38 C39 C34 114.9(3) . . ? C38 C39 H39A 108.5 . . ? C34 C39 H39A 108.5 . . ? C38 C39 H39B 108.5 . . ? C34 C39 H39B 108.5 . . ? H39A C39 H39B 107.5 . . ? N4 C40 C41 123.6(3) . . ? N4 C40 H40 118.2 . . ? C41 C40 H40 118.2 . . ? C42 C41 C40 122.7(3) . . ? C42 C41 H41 118.7 . . ? C40 C41 H41 118.7 . . ? C41 C42 C43 126.9(4) . . ? C41 C42 H42 116.5 . . ? C43 C42 H42 116.5 . . ? C48 C43 C44 118.6(4) . . ? C48 C43 C42 122.3(3) . . ? C44 C43 C42 119.1(4) . . ? C45 C44 C43 120.2(4) . . ? C45 C44 H44 119.9 . . ? C43 C44 H44 119.9 . . ? C46 C45 C44 120.7(4) . . ? C46 C45 H45 119.7 . . ? C44 C45 H45 119.7 . . ? C45 C46 C47 119.8(4) . . ? C45 C46 H46 120.1 . . ? C47 C46 H46 120.1 . . ? C48 C47 C46 120.0(4) . . ? C48 C47 H47 120.0 . . ? C46 C47 H47 120.0 . . ? C47 C48 C43 120.6(4) . . ? C47 C48 H48 119.7 . . ? C43 C48 H48 119.7 . . ? N5 C49 C50 122.8(3) . . ? N5 C49 H49 118.6 . . ? C50 C49 H49 118.6 . . ? C51 C50 C49 123.1(4) . . ? C51 C50 H50 118.4 . . ? C49 C50 H50 118.4 . . ? C50 C51 C52 126.3(4) . . ? C50 C51 H51 116.9 . . ? C52 C51 H51 116.9 . . ? C57 C52 C53 118.9(3) . . ? C57 C52 C51 122.6(4) . . ? C53 C52 C51 118.5(4) . . ? C54 C53 C52 119.8(4) . . ? C54 C53 H53 120.1 . . ? C52 C53 H53 120.1 . . ? C55 C54 C53 120.4(4) . . ? C55 C54 H54 119.8 . . ? C53 C54 H54 119.8 . . ? C54 C55 C56 120.0(4) . . ? C54 C55 H55 120.0 . . ? C56 C55 H55 120.0 . . ? C57 C56 C55 120.3(4) . . ? C57 C56 H56 119.8 . . ? C55 C56 H56 119.8 . . ? C56 C57 C52 120.5(4) . . ? C56 C57 H57 119.8 . . ? C52 C57 H57 119.8 . . ? N6 C58 C59 121.9(3) . . ? N6 C58 H58 119.0 . . ? C59 C58 H58 119.0 . . ? C60 C59 C58 122.5(3) . . ? C60 C59 H59 118.8 . . ? C58 C59 H59 118.8 . . ? C59 C60 C61 126.3(4) . . ? C59 C60 H60 116.9 . . ? C61 C60 H60 116.9 . . ? C66 C61 C62 118.1(3) . . ? C66 C61 C60 122.3(3) . . ? C62 C61 C60 119.6(3) . . ? C63 C62 C61 120.9(4) . . ? C63 C62 H62 119.5 . . ? C61 C62 H62 119.5 . . ? C64 C63 C62 120.2(4) . . ? C64 C63 H63 119.9 . . ? C62 C63 H63 119.9 . . ? C63 C64 C65 119.9(4) . . ? C63 C64 H64 120.0 . . ? C65 C64 H64 120.0 . . ? C66 C65 C64 120.2(4) . . ? C66 C65 H65 119.9 . . ? C64 C65 H65 119.9 . . ? C65 C66 C61 120.6(4) . . ? C65 C66 H66 119.7 . . ? C61 C66 H66 119.7 . . ? N3 Cu1 N2 95.85(12) . . ? N3 Cu1 N1 93.91(11) . . ? N2 Cu1 N1 92.44(12) . . ? N3 Cu1 Br1 123.16(9) . . ? N2 Cu1 Br1 120.91(8) . . ? N1 Cu1 Br1 122.87(8) . . ? N4 Cu2 N5 94.28(12) . . ? N4 Cu2 N6 95.45(11) . . ? N5 Cu2 N6 93.74(12) . . ? N4 Cu2 Br2 122.98(8) . . ? N5 Cu2 Br2 120.71(8) . . ? N6 Cu2 Br2 122.31(8) . . ? C7 N1 C1 118.2(3) . . ? C7 N1 Cu1 128.9(2) . . ? C1 N1 Cu1 112.5(2) . . ? C16 N2 C3 116.9(3) . . ? C16 N2 Cu1 130.3(2) . . ? C3 N2 Cu1 112.3(2) . . ? C25 N3 C5 118.1(3) . . ? C25 N3 Cu1 129.2(3) . . ? C5 N3 Cu1 112.7(2) . . ? C40 N4 C34 117.5(3) . . ? C40 N4 Cu2 130.4(2) . . ? C34 N4 Cu2 111.9(2) . . ? C49 N5 C36 116.7(3) . . ? C49 N5 Cu2 131.2(3) . . ? C36 N5 Cu2 112.1(2) . . ? C58 N6 C38 117.9(3) . . ? C58 N6 Cu2 130.0(2) . . ? C38 N6 Cu2 112.0(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -72.0(4) . . . . ? C6 C1 C2 C3 51.4(4) . . . . ? C1 C2 C3 N2 73.1(4) . . . . ? C1 C2 C3 C4 -50.3(4) . . . . ? N2 C3 C4 C5 -72.8(4) . . . . ? C2 C3 C4 C5 49.2(4) . . . . ? C3 C4 C5 N3 74.0(4) . . . . ? C3 C4 C5 C6 -49.3(4) . . . . ? N1 C1 C6 C5 71.7(4) . . . . ? C2 C1 C6 C5 -51.6(4) . . . . ? N3 C5 C6 C1 -72.2(4) . . . . ? C4 C5 C6 C1 50.3(4) . . . . ? N1 C7 C8 C9 -177.8(4) . . . . ? C7 C8 C9 C10 178.9(3) . . . . ? C8 C9 C10 C11 -174.0(4) . . . . ? C8 C9 C10 C15 5.8(6) . . . . ? C15 C10 C11 C12 0.0(6) . . . . ? C9 C10 C11 C12 179.9(4) . . . . ? C10 C11 C12 C13 0.1(6) . . . . ? C11 C12 C13 C14 0.3(6) . . . . ? C12 C13 C14 C15 -0.8(6) . . . . ? C13 C14 C15 C10 0.9(6) . . . . ? C11 C10 C15 C14 -0.5(6) . . . . ? C9 C10 C15 C14 179.6(4) . . . . ? N2 C16 C17 C18 171.1(4) . . . . ? C16 C17 C18 C19 -173.7(3) . . . . ? C17 C18 C19 C24 2.8(6) . . . . ? C17 C18 C19 C20 -178.2(4) . . . . ? C24 C19 C20 C21 -0.5(6) . . . . ? C18 C19 C20 C21 -179.5(4) . . . . ? C19 C20 C21 C22 0.8(7) . . . . ? C20 C21 C22 C23 -0.9(7) . . . . ? C21 C22 C23 C24 0.7(7) . . . . ? C20 C19 C24 C23 0.3(6) . . . . ? C18 C19 C24 C23 179.3(4) . . . . ? C22 C23 C24 C19 -0.4(6) . . . . ? N3 C25 C26 C27 -179.8(4) . . . . ? C25 C26 C27 C28 177.0(3) . . . . ? C26 C27 C28 C29 175.6(4) . . . . ? C26 C27 C28 C33 -5.4(6) . . . . ? C33 C28 C29 C30 -0.3(6) . . . . ? C27 C28 C29 C30 178.8(4) . . . . ? C28 C29 C30 C31 0.9(6) . . . . ? C29 C30 C31 C32 -1.1(6) . . . . ? C30 C31 C32 C33 0.8(6) . . . . ? C31 C32 C33 C28 -0.2(6) . . . . ? C29 C28 C33 C32 -0.1(5) . . . . ? C27 C28 C33 C32 -179.2(3) . . . . ? N4 C34 C35 C36 -73.2(4) . . . . ? C39 C34 C35 C36 50.1(4) . . . . ? C34 C35 C36 N5 72.9(4) . . . . ? C34 C35 C36 C37 -49.9(4) . . . . ? N5 C36 C37 C38 -72.9(4) . . . . ? C35 C36 C37 C38 49.0(4) . . . . ? C36 C37 C38 N6 74.1(4) . . . . ? C36 C37 C38 C39 -49.7(4) . . . . ? N6 C38 C39 C34 -72.6(4) . . . . ? C37 C38 C39 C34 49.8(4) . . . . ? N4 C34 C39 C38 73.1(4) . . . . ? C35 C34 C39 C38 -49.9(4) . . . . ? N4 C40 C41 C42 176.0(4) . . . . ? C40 C41 C42 C43 -174.2(3) . . . . ? C41 C42 C43 C48 1.4(6) . . . . ? C41 C42 C43 C44 179.1(4) . . . . ? C48 C43 C44 C45 1.8(6) . . . . ? C42 C43 C44 C45 -176.0(4) . . . . ? C43 C44 C45 C46 -0.2(7) . . . . ? C44 C45 C46 C47 -1.8(7) . . . . ? C45 C46 C47 C48 2.0(6) . . . . ? C46 C47 C48 C43 -0.4(6) . . . . ? C44 C43 C48 C47 -1.5(6) . . . . ? C42 C43 C48 C47 176.2(3) . . . . ? N5 C49 C50 C51 -174.1(3) . . . . ? C49 C50 C51 C52 178.5(3) . . . . ? C50 C51 C52 C57 -3.3(6) . . . . ? C50 C51 C52 C53 175.4(4) . . . . ? C57 C52 C53 C54 2.3(5) . . . . ? C51 C52 C53 C54 -176.4(3) . . . . ? C52 C53 C54 C55 0.0(6) . . . . ? C53 C54 C55 C56 -1.4(6) . . . . ? C54 C55 C56 C57 0.6(5) . . . . ? C55 C56 C57 C52 1.8(5) . . . . ? C53 C52 C57 C56 -3.2(5) . . . . ? C51 C52 C57 C56 175.4(3) . . . . ? N6 C58 C59 C60 172.1(4) . . . . ? C58 C59 C60 C61 -173.1(4) . . . . ? C59 C60 C61 C66 -3.5(6) . . . . ? C59 C60 C61 C62 174.1(4) . . . . ? C66 C61 C62 C63 1.4(6) . . . . ? C60 C61 C62 C63 -176.3(4) . . . . ? C61 C62 C63 C64 -0.9(6) . . . . ? C62 C63 C64 C65 -0.1(6) . . . . ? C63 C64 C65 C66 0.5(6) . . . . ? C64 C65 C66 C61 0.0(6) . . . . ? C62 C61 C66 C65 -1.0(6) . . . . ? C60 C61 C66 C65 176.6(4) . . . . ? C8 C7 N1 C1 179.8(3) . . . . ? C8 C7 N1 Cu1 7.4(5) . . . . ? C2 C1 N1 C7 -111.3(4) . . . . ? C6 C1 N1 C7 125.4(3) . . . . ? C2 C1 N1 Cu1 62.3(3) . . . . ? C6 C1 N1 Cu1 -61.0(3) . . . . ? N3 Cu1 N1 C7 -140.4(3) . . . . ? N2 Cu1 N1 C7 123.6(3) . . . . ? Br1 Cu1 N1 C7 -6.2(4) . . . . ? N3 Cu1 N1 C1 46.9(2) . . . . ? N2 Cu1 N1 C1 -49.2(2) . . . . ? Br1 Cu1 N1 C1 -178.9(2) . . . . ? C17 C16 N2 C3 -174.2(3) . . . . ? C17 C16 N2 Cu1 -3.7(5) . . . . ? C4 C3 N2 C16 -129.8(4) . . . . ? C2 C3 N2 C16 107.3(4) . . . . ? C4 C3 N2 Cu1 58.0(3) . . . . ? C2 C3 N2 Cu1 -64.9(3) . . . . ? N3 Cu1 N2 C16 145.8(3) . . . . ? N1 Cu1 N2 C16 -120.0(3) . . . . ? Br1 Cu1 N2 C16 11.2(4) . . . . ? N3 Cu1 N2 C3 -43.4(2) . . . . ? N1 Cu1 N2 C3 50.8(2) . . . . ? Br1 Cu1 N2 C3 -178.0(2) . . . . ? C26 C25 N3 C5 177.2(3) . . . . ? C26 C25 N3 Cu1 -2.3(5) . . . . ? C4 C5 N3 C25 119.2(4) . . . . ? C6 C5 N3 C25 -117.7(4) . . . . ? C4 C5 N3 Cu1 -61.1(3) . . . . ? C6 C5 N3 Cu1 61.9(4) . . . . ? N2 Cu1 N3 C25 -134.8(3) . . . . ? N1 Cu1 N3 C25 132.3(3) . . . . ? Br1 Cu1 N3 C25 -1.7(4) . . . . ? N2 Cu1 N3 C5 45.6(2) . . . . ? N1 Cu1 N3 C5 -47.2(2) . . . . ? Br1 Cu1 N3 C5 178.78(19) . . . . ? C41 C40 N4 C34 -178.3(3) . . . . ? C41 C40 N4 Cu2 6.9(5) . . . . ? C35 C34 N4 C40 -113.8(4) . . . . ? C39 C34 N4 C40 123.0(3) . . . . ? C35 C34 N4 Cu2 61.9(3) . . . . ? C39 C34 N4 Cu2 -61.2(3) . . . . ? N5 Cu2 N4 C40 127.0(3) . . . . ? N6 Cu2 N4 C40 -138.8(3) . . . . ? Br2 Cu2 N4 C40 -4.2(4) . . . . ? N5 Cu2 N4 C34 -48.0(2) . . . . ? N6 Cu2 N4 C34 46.2(2) . . . . ? Br2 Cu2 N4 C34 -179.25(19) . . . . ? C50 C49 N5 C36 -179.7(3) . . . . ? C50 C49 N5 Cu2 1.9(5) . . . . ? C37 C36 N5 C49 -117.7(3) . . . . ? C35 C36 N5 C49 119.7(3) . . . . ? C37 C36 N5 Cu2 61.0(3) . . . . ? C35 C36 N5 Cu2 -61.6(3) . . . . ? N4 Cu2 N5 C49 -133.0(3) . . . . ? N6 Cu2 N5 C49 131.3(3) . . . . ? Br2 Cu2 N5 C49 -0.2(4) . . . . ? N4 Cu2 N5 C36 48.6(2) . . . . ? N6 Cu2 N5 C36 -47.2(2) . . . . ? Br2 Cu2 N5 C36 -178.60(18) . . . . ? C59 C58 N6 C38 -176.5(3) . . . . ? C59 C58 N6 Cu2 -1.4(5) . . . . ? C39 C38 N6 C58 -124.0(3) . . . . ? C37 C38 N6 C58 112.2(4) . . . . ? C39 C38 N6 Cu2 60.0(3) . . . . ? C37 C38 N6 Cu2 -63.8(3) . . . . ? N4 Cu2 N6 C58 139.2(3) . . . . ? N5 Cu2 N6 C58 -126.1(3) . . . . ? Br2 Cu2 N6 C58 4.2(4) . . . . ? N4 Cu2 N6 C38 -45.4(2) . . . . ? N5 Cu2 N6 C38 49.3(2) . . . . ? Br2 Cu2 N6 C38 179.57(19) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.573 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.080 data_phw0507m _database_code_depnum_ccdc_archive 'CCDC 279583' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H33 Cu N4 O2' _chemical_formula_sum 'C33 H33 Cu N4 O2' _chemical_formula_weight 581.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 12.2294(10) _cell_length_b 13.5896(11) _cell_length_c 17.0826(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2839.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7733 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 28.54 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.806 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.805 _exptl_absorpt_correction_T_max 0.870 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39581 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 29.06 _reflns_number_total 7567 _reflns_number_gt 6994 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.002(6) _refine_ls_number_reflns 7567 _refine_ls_number_parameters 361 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0643 _refine_ls_wR_factor_gt 0.0632 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _refine_ls_shift/su_max 0.002 _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 0.37808(13) 0.71731(11) 0.54519(9) 0.0257(3) Uani 1 1 d . . . H1 H 0.4038 0.7748 0.5136 0.031 Uiso 1 1 calc R . . C2 C 0.35583(14) 0.75228(12) 0.62831(10) 0.0288(3) Uani 1 1 d . . . H2A H 0.2908 0.7957 0.6274 0.035 Uiso 1 1 calc R . . H2B H 0.4187 0.7925 0.6458 0.035 Uiso 1 1 calc R . . C3 C 0.33637(13) 0.67119(12) 0.68885(9) 0.0265(3) Uani 1 1 d . . . H3 H 0.3388 0.7015 0.7422 0.032 Uiso 1 1 calc R . . C4 C 0.42562(13) 0.59193(13) 0.68423(9) 0.0268(3) Uani 1 1 d . . . H4A H 0.4035 0.5357 0.7175 0.032 Uiso 1 1 calc R . . H4B H 0.4940 0.6192 0.7064 0.032 Uiso 1 1 calc R . . C5 C 0.44982(13) 0.55340(11) 0.60146(10) 0.0251(3) Uani 1 1 d . . . H5 H 0.5182 0.5132 0.6035 0.030 Uiso 1 1 calc R . . C6 C 0.46792(12) 0.63846(12) 0.54448(9) 0.0273(3) Uani 1 1 d . . . H6A H 0.4737 0.6113 0.4909 0.033 Uiso 1 1 calc R . . H6B H 0.5386 0.6703 0.5571 0.033 Uiso 1 1 calc R . . C7 C 0.24613(14) 0.71865(11) 0.44502(9) 0.0240(3) Uani 1 1 d . . . H7 H 0.2917 0.7673 0.4219 0.029 Uiso 1 1 calc R . . C8 C 0.14634(13) 0.69231(11) 0.40577(9) 0.0238(3) Uani 1 1 d . . . H8 H 0.0972 0.6481 0.4307 0.029 Uiso 1 1 calc R . . C9 C 0.12071(13) 0.72812(11) 0.33545(10) 0.0258(3) Uani 1 1 d . . . H9 H 0.1705 0.7736 0.3128 0.031 Uiso 1 1 calc R . . C10 C 0.02322(12) 0.70395(11) 0.28995(9) 0.0240(3) Uani 1 1 d . . . C11 C 0.01341(14) 0.74114(12) 0.21368(10) 0.0294(3) Uani 1 1 d . . . H11 H 0.0684 0.7834 0.1934 0.035 Uiso 1 1 calc R . . C12 C -0.07606(15) 0.71668(13) 0.16747(10) 0.0332(4) Uani 1 1 d . . . H12 H -0.0821 0.7419 0.1158 0.040 Uiso 1 1 calc R . . C13 C -0.15631(14) 0.65547(13) 0.19706(10) 0.0310(3) Uani 1 1 d . . . H13 H -0.2177 0.6388 0.1657 0.037 Uiso 1 1 calc R . . C14 C -0.14755(13) 0.61869(12) 0.27180(10) 0.0282(3) Uani 1 1 d . . . H14 H -0.2030 0.5765 0.2917 0.034 Uiso 1 1 calc R . . C15 C -0.05845(12) 0.64256(12) 0.31856(9) 0.0251(3) Uani 1 1 d . . . H15 H -0.0533 0.6169 0.3702 0.030 Uiso 1 1 calc R . . C16 C 0.15837(13) 0.63412(12) 0.73363(9) 0.0242(3) Uani 1 1 d . . . H16 H 0.1783 0.6674 0.7804 0.029 Uiso 1 1 calc R . . C17 C 0.05039(12) 0.59265(11) 0.72650(9) 0.0229(3) Uani 1 1 d . . . H17 H 0.0313 0.5636 0.6778 0.027 Uiso 1 1 calc R . . C18 C -0.02513(12) 0.59197(12) 0.78333(9) 0.0234(3) Uani 1 1 d . . . H18 H -0.0073 0.6232 0.8314 0.028 Uiso 1 1 calc R . . C19 C -0.13363(12) 0.54636(10) 0.77652(9) 0.0222(3) Uani 1 1 d . . . C20 C -0.20364(13) 0.54692(12) 0.84115(10) 0.0260(3) Uani 1 1 d . . . H20 H -0.1808 0.5781 0.8882 0.031 Uiso 1 1 calc R . . C21 C -0.30528(13) 0.50301(12) 0.83800(11) 0.0310(4) Uani 1 1 d . . . H21 H -0.3523 0.5055 0.8822 0.037 Uiso 1 1 calc R . . C22 C -0.33887(13) 0.45554(12) 0.77076(11) 0.0317(4) Uani 1 1 d . . . H22 H -0.4081 0.4239 0.7690 0.038 Uiso 1 1 calc R . . C23 C -0.27058(15) 0.45427(14) 0.70540(11) 0.0321(4) Uani 1 1 d . . . H23 H -0.2935 0.4222 0.6588 0.038 Uiso 1 1 calc R . . C24 C -0.16919(14) 0.49974(12) 0.70843(9) 0.0280(3) Uani 1 1 d . . . H24 H -0.1234 0.4991 0.6635 0.034 Uiso 1 1 calc R . . C25 C 0.38484(11) 0.40230(11) 0.55279(8) 0.0210(3) Uani 1 1 d . . . H25 H 0.4582 0.3804 0.5582 0.025 Uiso 1 1 calc R . . C26 C 0.30379(11) 0.33519(11) 0.52141(9) 0.0207(3) Uani 1 1 d . . . H26 H 0.2316 0.3588 0.5133 0.025 Uiso 1 1 calc R . . C27 C 0.32606(12) 0.24136(11) 0.50330(8) 0.0219(3) Uani 1 1 d . . . H27 H 0.3981 0.2185 0.5133 0.026 Uiso 1 1 calc R . . C28 C 0.24837(13) 0.17112(11) 0.46941(9) 0.0216(3) Uani 1 1 d . . . C29 C 0.27604(14) 0.07140(11) 0.46723(11) 0.0283(3) Uani 1 1 d . . . H29 H 0.3439 0.0499 0.4882 0.034 Uiso 1 1 calc R . . C30 C 0.20453(14) 0.00376(13) 0.43456(12) 0.0328(4) Uani 1 1 d . . . H30 H 0.2233 -0.0641 0.4345 0.039 Uiso 1 1 calc R . . C31 C 0.10685(13) 0.03333(13) 0.40224(10) 0.0288(3) Uani 1 1 d . . . H31 H 0.0596 -0.0135 0.3785 0.035 Uiso 1 1 calc R . . C32 C 0.07768(12) 0.13191(12) 0.40448(9) 0.0258(3) Uani 1 1 d . . . H32 H 0.0100 0.1527 0.3827 0.031 Uiso 1 1 calc R . . C33 C 0.14720(12) 0.20003(11) 0.43844(9) 0.0232(3) Uani 1 1 d . . . H33 H 0.1261 0.2672 0.4408 0.028 Uiso 1 1 calc R . . Cu1 Cu 0.209582(12) 0.563107(11) 0.568774(12) 0.01897(5) Uani 1 1 d . . . N1 N 0.27647(10) 0.67946(9) 0.50976(8) 0.0233(3) Uani 1 1 d . . . N2 N 0.22809(10) 0.62673(9) 0.67771(8) 0.0224(3) Uani 1 1 d . . . N3 N 0.36039(8) 0.49017(8) 0.57343(8) 0.0210(2) Uani 1 1 d . . . N4 N 0.06790(9) 0.50451(8) 0.53234(7) 0.0171(2) Uani 1 1 d . . . O1 O -0.01266(9) 0.56001(7) 0.53425(7) 0.0283(2) Uani 1 1 d . . . O2 O 0.05713(9) 0.42150(8) 0.50651(7) 0.0285(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0272(7) 0.0243(7) 0.0255(7) -0.0001(6) -0.0036(6) -0.0094(6) C2 0.0281(8) 0.0272(7) 0.0310(8) -0.0063(6) -0.0049(6) -0.0087(6) C3 0.0243(7) 0.0327(8) 0.0225(7) -0.0069(6) -0.0034(6) -0.0049(6) C4 0.0199(7) 0.0366(8) 0.0239(7) -0.0013(6) -0.0066(6) -0.0032(6) C5 0.0166(7) 0.0327(8) 0.0259(7) -0.0022(6) -0.0033(6) -0.0022(6) C6 0.0195(7) 0.0346(8) 0.0278(8) -0.0025(6) 0.0004(5) -0.0098(6) C7 0.0271(7) 0.0198(7) 0.0249(7) 0.0010(6) 0.0004(6) -0.0030(6) C8 0.0247(7) 0.0220(7) 0.0249(7) 0.0019(6) 0.0006(6) 0.0013(6) C9 0.0275(7) 0.0251(7) 0.0250(7) 0.0026(6) 0.0015(6) -0.0005(6) C10 0.0278(7) 0.0226(7) 0.0215(7) -0.0011(5) 0.0000(6) 0.0060(6) C11 0.0328(8) 0.0320(8) 0.0236(8) 0.0056(6) 0.0005(6) 0.0008(7) C12 0.0401(9) 0.0384(9) 0.0211(8) -0.0001(7) -0.0046(7) 0.0063(8) C13 0.0287(8) 0.0360(8) 0.0281(8) -0.0089(7) -0.0050(6) 0.0056(7) C14 0.0241(7) 0.0282(8) 0.0322(8) -0.0036(7) 0.0021(6) 0.0021(6) C15 0.0264(7) 0.0272(8) 0.0218(7) -0.0008(6) 0.0022(6) 0.0061(6) C16 0.0263(7) 0.0270(8) 0.0193(7) -0.0026(6) -0.0031(6) 0.0034(6) C17 0.0242(7) 0.0244(7) 0.0200(7) 0.0007(6) -0.0030(6) 0.0041(6) C18 0.0243(7) 0.0253(7) 0.0207(7) -0.0008(6) -0.0015(6) 0.0035(6) C19 0.0226(7) 0.0217(7) 0.0225(7) 0.0022(6) 0.0002(5) 0.0049(5) C20 0.0274(8) 0.0279(8) 0.0227(8) 0.0003(6) 0.0012(6) 0.0030(6) C21 0.0281(8) 0.0346(9) 0.0303(9) 0.0032(7) 0.0055(6) 0.0036(6) C22 0.0218(8) 0.0347(9) 0.0386(9) -0.0003(7) 0.0002(7) 0.0018(6) C23 0.0292(8) 0.0380(10) 0.0289(9) -0.0019(7) -0.0050(7) -0.0002(7) C24 0.0278(8) 0.0331(8) 0.0231(7) 0.0004(6) 0.0008(6) 0.0022(7) C25 0.0161(6) 0.0289(7) 0.0181(8) 0.0016(5) -0.0004(5) 0.0010(5) C26 0.0171(6) 0.0269(7) 0.0180(6) 0.0015(5) -0.0003(5) 0.0008(5) C27 0.0165(6) 0.0280(7) 0.0211(7) 0.0008(6) -0.0001(5) 0.0042(5) C28 0.0208(6) 0.0246(7) 0.0195(7) -0.0003(5) 0.0033(6) 0.0023(6) C29 0.0267(8) 0.0269(8) 0.0312(9) -0.0018(6) -0.0022(6) 0.0086(6) C30 0.0369(10) 0.0225(8) 0.0390(10) -0.0038(7) 0.0007(7) 0.0052(6) C31 0.0306(8) 0.0272(7) 0.0286(8) -0.0043(7) 0.0035(7) -0.0052(6) C32 0.0206(7) 0.0312(8) 0.0255(7) 0.0011(6) 0.0005(6) 0.0000(6) C33 0.0211(7) 0.0229(7) 0.0257(7) 0.0013(6) 0.0019(6) 0.0026(6) Cu1 0.01681(7) 0.02048(8) 0.01961(8) -0.00042(8) -0.00252(8) -0.00255(6) N1 0.0250(6) 0.0219(6) 0.0228(6) -0.0012(5) -0.0026(5) -0.0032(5) N2 0.0202(6) 0.0248(6) 0.0222(6) -0.0013(5) -0.0031(5) -0.0005(5) N3 0.0168(5) 0.0282(6) 0.0181(5) 0.0015(6) -0.0020(5) -0.0025(4) N4 0.0213(6) 0.0181(5) 0.0121(5) 0.0023(4) 0.0019(4) 0.0050(4) O1 0.0213(5) 0.0266(6) 0.0370(6) -0.0048(5) -0.0049(5) 0.0045(4) O2 0.0214(5) 0.0241(5) 0.0400(7) -0.0071(5) -0.0022(5) -0.0008(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.4747(19) . ? C1 C2 1.522(2) . ? C1 C6 1.535(2) . ? C1 H1 1.0000 . ? C2 C3 1.530(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N2 1.468(2) . ? C3 C4 1.536(2) . ? C3 H3 1.0000 . ? C4 C5 1.536(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N3 1.4709(18) . ? C5 C6 1.527(2) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N1 1.282(2) . ? C7 C8 1.438(2) . ? C7 H7 0.9500 . ? C8 C9 1.333(2) . ? C8 H8 0.9500 . ? C9 C10 1.461(2) . ? C9 H9 0.9500 . ? C10 C15 1.390(2) . ? C10 C11 1.403(2) . ? C11 C12 1.390(2) . ? C11 H11 0.9500 . ? C12 C13 1.382(3) . ? C12 H12 0.9500 . ? C13 C14 1.375(2) . ? C13 H13 0.9500 . ? C14 C15 1.389(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 N2 1.284(2) . ? C16 C17 1.441(2) . ? C16 H16 0.9500 . ? C17 C18 1.340(2) . ? C17 H17 0.9500 . ? C18 C19 1.469(2) . ? C18 H18 0.9500 . ? C19 C24 1.394(2) . ? C19 C20 1.397(2) . ? C20 C21 1.380(2) . ? C20 H20 0.9500 . ? C21 C22 1.380(3) . ? C21 H21 0.9500 . ? C22 C23 1.394(3) . ? C22 H22 0.9500 . ? C23 C24 1.386(3) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 N3 1.2806(19) . ? C25 C26 1.450(2) . ? C25 H25 0.9500 . ? C26 C27 1.340(2) . ? C26 H26 0.9500 . ? C27 C28 1.466(2) . ? C27 H27 0.9500 . ? C28 C29 1.397(2) . ? C28 C33 1.402(2) . ? C29 C30 1.386(2) . ? C29 H29 0.9500 . ? C30 C31 1.376(2) . ? C30 H30 0.9500 . ? C31 C32 1.387(2) . ? C31 H31 0.9500 . ? C32 C33 1.384(2) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? Cu1 N4 2.0059(12) . ? Cu1 N1 2.0459(13) . ? Cu1 N2 2.0644(13) . ? Cu1 N3 2.0952(11) . ? N4 O2 1.2185(15) . ? N4 O1 1.2412(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 109.95(13) . . ? N1 C1 C6 110.88(12) . . ? C2 C1 C6 110.69(13) . . ? N1 C1 H1 108.4 . . ? C2 C1 H1 108.4 . . ? C6 C1 H1 108.4 . . ? C1 C2 C3 115.69(13) . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2B 108.4 . . ? C3 C2 H2B 108.4 . . ? H2A C2 H2B 107.4 . . ? N2 C3 C2 110.44(13) . . ? N2 C3 C4 110.23(13) . . ? C2 C3 C4 111.09(13) . . ? N2 C3 H3 108.3 . . ? C2 C3 H3 108.3 . . ? C4 C3 H3 108.3 . . ? C3 C4 C5 115.04(13) . . ? C3 C4 H4A 108.5 . . ? C5 C4 H4A 108.5 . . ? C3 C4 H4B 108.5 . . ? C5 C4 H4B 108.5 . . ? H4A C4 H4B 107.5 . . ? N3 C5 C6 110.02(13) . . ? N3 C5 C4 110.82(13) . . ? C6 C5 C4 110.89(13) . . ? N3 C5 H5 108.3 . . ? C6 C5 H5 108.3 . . ? C4 C5 H5 108.3 . . ? C5 C6 C1 114.81(13) . . ? C5 C6 H6A 108.6 . . ? C1 C6 H6A 108.6 . . ? C5 C6 H6B 108.6 . . ? C1 C6 H6B 108.6 . . ? H6A C6 H6B 107.5 . . ? N1 C7 C8 122.99(14) . . ? N1 C7 H7 118.5 . . ? C8 C7 H7 118.5 . . ? C9 C8 C7 121.92(14) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C8 C9 C10 126.09(14) . . ? C8 C9 H9 117.0 . . ? C10 C9 H9 117.0 . . ? C15 C10 C11 118.78(15) . . ? C15 C10 C9 122.30(14) . . ? C11 C10 C9 118.88(15) . . ? C12 C11 C10 120.58(16) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C13 C12 C11 119.69(16) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C14 C13 C12 120.19(15) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 120.66(16) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C10 120.10(15) . . ? C14 C15 H15 120.0 . . ? C10 C15 H15 120.0 . . ? N2 C16 C17 120.99(14) . . ? N2 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C18 C17 C16 124.96(14) . . ? C18 C17 H17 117.5 . . ? C16 C17 H17 117.5 . . ? C17 C18 C19 124.61(14) . . ? C17 C18 H18 117.7 . . ? C19 C18 H18 117.7 . . ? C24 C19 C20 118.07(14) . . ? C24 C19 C18 122.66(14) . . ? C20 C19 C18 119.25(14) . . ? C21 C20 C19 121.26(16) . . ? C21 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C22 C21 C20 120.18(16) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 119.60(16) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C24 C23 C22 120.02(17) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C19 120.85(15) . . ? C23 C24 H24 119.6 . . ? C19 C24 H24 119.6 . . ? N3 C25 C26 121.93(13) . . ? N3 C25 H25 119.0 . . ? C26 C25 H25 119.0 . . ? C27 C26 C25 123.02(13) . . ? C27 C26 H26 118.5 . . ? C25 C26 H26 118.5 . . ? C26 C27 C28 125.38(13) . . ? C26 C27 H27 117.3 . . ? C28 C27 H27 117.3 . . ? C29 C28 C33 118.39(14) . . ? C29 C28 C27 119.01(14) . . ? C33 C28 C27 122.59(13) . . ? C30 C29 C28 120.07(15) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C31 C30 C29 121.04(16) . . ? C31 C30 H30 119.5 . . ? C29 C30 H30 119.5 . . ? C30 C31 C32 119.62(15) . . ? C30 C31 H31 120.2 . . ? C32 C31 H31 120.2 . . ? C33 C32 C31 119.97(15) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C32 C33 C28 120.86(14) . . ? C32 C33 H33 119.6 . . ? C28 C33 H33 119.6 . . ? N4 Cu1 N1 119.96(5) . . ? N4 Cu1 N2 122.73(5) . . ? N1 Cu1 N2 94.39(5) . . ? N4 Cu1 N3 125.76(5) . . ? N1 Cu1 N3 91.85(5) . . ? N2 Cu1 N3 93.86(5) . . ? C7 N1 C1 116.93(13) . . ? C7 N1 Cu1 129.06(11) . . ? C1 N1 Cu1 113.85(10) . . ? C16 N2 C3 118.05(13) . . ? C16 N2 Cu1 129.08(11) . . ? C3 N2 Cu1 112.84(9) . . ? C25 N3 C5 117.44(12) . . ? C25 N3 Cu1 129.51(9) . . ? C5 N3 Cu1 112.98(9) . . ? O2 N4 O1 119.09(12) . . ? O2 N4 Cu1 124.98(9) . . ? O1 N4 Cu1 115.87(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 72.63(17) . . . . ? C6 C1 C2 C3 -50.22(18) . . . . ? C1 C2 C3 N2 -73.51(17) . . . . ? C1 C2 C3 C4 49.13(18) . . . . ? N2 C3 C4 C5 74.15(17) . . . . ? C2 C3 C4 C5 -48.61(17) . . . . ? C3 C4 C5 N3 -72.66(17) . . . . ? C3 C4 C5 C6 49.83(18) . . . . ? N3 C5 C6 C1 71.86(16) . . . . ? C4 C5 C6 C1 -51.10(17) . . . . ? N1 C1 C6 C5 -71.14(16) . . . . ? C2 C1 C6 C5 51.17(17) . . . . ? N1 C7 C8 C9 -174.47(16) . . . . ? C7 C8 C9 C10 178.22(14) . . . . ? C8 C9 C10 C15 3.5(3) . . . . ? C8 C9 C10 C11 -174.16(16) . . . . ? C15 C10 C11 C12 -0.3(2) . . . . ? C9 C10 C11 C12 177.49(15) . . . . ? C10 C11 C12 C13 0.3(3) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C12 C13 C14 C15 0.2(2) . . . . ? C13 C14 C15 C10 -0.2(2) . . . . ? C11 C10 C15 C14 0.3(2) . . . . ? C9 C10 C15 C14 -177.45(14) . . . . ? N2 C16 C17 C18 175.99(15) . . . . ? C16 C17 C18 C19 -177.67(14) . . . . ? C17 C18 C19 C24 -0.9(2) . . . . ? C17 C18 C19 C20 177.34(15) . . . . ? C24 C19 C20 C21 -0.2(2) . . . . ? C18 C19 C20 C21 -178.51(15) . . . . ? C19 C20 C21 C22 1.4(2) . . . . ? C20 C21 C22 C23 -1.6(3) . . . . ? C21 C22 C23 C24 0.6(3) . . . . ? C22 C23 C24 C19 0.6(3) . . . . ? C20 C19 C24 C23 -0.8(2) . . . . ? C18 C19 C24 C23 177.48(15) . . . . ? N3 C25 C26 C27 -176.35(15) . . . . ? C25 C26 C27 C28 -178.17(13) . . . . ? C26 C27 C28 C29 -167.99(16) . . . . ? C26 C27 C28 C33 12.4(2) . . . . ? C33 C28 C29 C30 0.4(3) . . . . ? C27 C28 C29 C30 -179.17(16) . . . . ? C28 C29 C30 C31 1.5(3) . . . . ? C29 C30 C31 C32 -2.0(3) . . . . ? C30 C31 C32 C33 0.6(2) . . . . ? C31 C32 C33 C28 1.3(2) . . . . ? C29 C28 C33 C32 -1.8(2) . . . . ? C27 C28 C33 C32 177.74(14) . . . . ? C8 C7 N1 C1 -177.06(14) . . . . ? C8 C7 N1 Cu1 7.9(2) . . . . ? C2 C1 N1 C7 124.00(15) . . . . ? C6 C1 N1 C7 -113.26(16) . . . . ? C2 C1 N1 Cu1 -60.16(14) . . . . ? C6 C1 N1 Cu1 62.58(14) . . . . ? N4 Cu1 N1 C7 -7.22(16) . . . . ? N2 Cu1 N1 C7 -139.30(14) . . . . ? N3 Cu1 N1 C7 126.68(14) . . . . ? N4 Cu1 N1 C1 177.56(9) . . . . ? N2 Cu1 N1 C1 45.48(11) . . . . ? N3 Cu1 N1 C1 -48.54(11) . . . . ? C17 C16 N2 C3 179.67(14) . . . . ? C17 C16 N2 Cu1 1.8(2) . . . . ? C2 C3 N2 C16 -117.79(15) . . . . ? C4 C3 N2 C16 119.07(15) . . . . ? C2 C3 N2 Cu1 60.43(14) . . . . ? C4 C3 N2 Cu1 -62.71(14) . . . . ? N4 Cu1 N2 C16 2.39(16) . . . . ? N1 Cu1 N2 C16 132.53(14) . . . . ? N3 Cu1 N2 C16 -135.31(14) . . . . ? N4 Cu1 N2 C3 -175.59(9) . . . . ? N1 Cu1 N2 C3 -45.44(11) . . . . ? N3 Cu1 N2 C3 46.72(11) . . . . ? C26 C25 N3 C5 -177.52(13) . . . . ? C26 C25 N3 Cu1 -0.8(2) . . . . ? C6 C5 N3 C25 113.96(15) . . . . ? C4 C5 N3 C25 -123.04(15) . . . . ? C6 C5 N3 Cu1 -63.33(14) . . . . ? C4 C5 N3 Cu1 59.67(15) . . . . ? N4 Cu1 N3 C25 2.05(16) . . . . ? N1 Cu1 N3 C25 -127.66(14) . . . . ? N2 Cu1 N3 C25 137.81(14) . . . . ? N4 Cu1 N3 C5 178.93(10) . . . . ? N1 Cu1 N3 C5 49.22(11) . . . . ? N2 Cu1 N3 C5 -45.31(11) . . . . ? N1 Cu1 N4 O2 114.47(12) . . . . ? N2 Cu1 N4 O2 -127.13(11) . . . . ? N3 Cu1 N4 O2 -2.97(14) . . . . ? N1 Cu1 N4 O1 -62.74(12) . . . . ? N2 Cu1 N4 O1 55.66(12) . . . . ? N3 Cu1 N4 O1 179.81(10) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.06 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.370 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.048