# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_contact_author_name 'Kai-Ju Wei' _publ_contact_author_address ; Department of Chemistry University of Science and Technology of China Hefei P. R. China. ; _publ_contact_author_email kjwei@ustc.edu.cn _publ_contact_author_fax +86-551-3600874 _publ_section_title ; Copper(I) Coordination Polymers of 2,2-Dipyridylamine Derivative: Syntheses, Structures, and Luminescence ; _publ_author_name 'Kaju Wei' #===END data_5 _database_code_depnum_ccdc_archive 'CCDC 279821' #TrackingRef '- 1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 Cu2 I2 N6' _chemical_formula_weight 873.45 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 18.6210(14) _cell_length_b 10.0925(8) _cell_length_c 18.7696(14) _cell_angle_alpha 90.00 _cell_angle_beta 117.6270(10) _cell_angle_gamma 90.00 _cell_volume 3125.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.856 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 3.369 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5823 _exptl_absorpt_correction_T_max 0.8770 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _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 APEX area-dectector diffractometer' _diffrn_measurement_method '\f and \w-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21927 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.0574 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5485 _reflns_number_gt 3633 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material SHELXL-97 _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^)+(0.0642P)^2^+1.3930P] 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 5485 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0938 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1393 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9447(6) 0.3469(10) 0.4346(6) 0.099(4) Uani 1 1 d . . . H1 H 0.9812 0.3637 0.4880 0.118 Uiso 1 1 calc R . . C2 C 0.8709(6) 0.3989(10) 0.4069(6) 0.085(3) Uani 1 1 d . . . H2 H 0.8573 0.4565 0.4374 0.103 Uiso 1 1 calc R . . C3 C 0.8171(5) 0.3623(9) 0.3313(6) 0.080(3) Uani 1 1 d . . . H3 H 0.7636 0.3908 0.3100 0.095 Uiso 1 1 calc R . . C4 C 0.8397(5) 0.2847(9) 0.2862(5) 0.066(2) Uani 1 1 d . . . H4 H 0.8021 0.2596 0.2346 0.079 Uiso 1 1 calc R . . C5 C 0.9184(4) 0.2437(6) 0.3175(4) 0.0369(16) Uani 1 1 d . . . C6 C 1.0291(4) 0.1268(6) 0.3034(4) 0.0354(16) Uani 1 1 d . . . C7 C 1.0673(4) 0.1442(7) 0.2555(4) 0.0471(18) Uani 1 1 d . . . H7 H 1.0402 0.1849 0.2055 0.056 Uiso 1 1 calc R . . C8 C 1.1441(5) 0.1012(8) 0.2824(5) 0.062(2) Uani 1 1 d . . . H8 H 1.1699 0.1099 0.2504 0.074 Uiso 1 1 calc R . . C9 C 1.1839(4) 0.0444(8) 0.3573(5) 0.058(2) Uani 1 1 d . . . H9 H 1.2371 0.0151 0.3771 0.069 Uiso 1 1 calc R . . C10 C 1.1437(4) 0.0319(8) 0.4017(4) 0.054(2) Uani 1 1 d . . . H10 H 1.1710 -0.0057 0.4526 0.065 Uiso 1 1 calc R . . C11 C 0.8932(4) 0.1283(6) 0.1935(4) 0.0343(15) Uani 1 1 d . . . C12 C 0.8550(5) 0.2183(7) 0.1314(4) 0.073(3) Uani 1 1 d . . . H12 H 0.8657 0.3083 0.1413 0.087 Uiso 1 1 calc R . . C13 C 0.8015(5) 0.1762(7) 0.0555(4) 0.066(2) Uani 1 1 d . . . H13 H 0.7758 0.2386 0.0150 0.079 Uiso 1 1 calc R . . C14 C 0.7850(4) 0.0424(6) 0.0378(4) 0.0353(16) Uani 1 1 d . . . C15 C 0.8277(4) -0.0439(7) 0.0990(4) 0.0436(17) Uani 1 1 d . . . H15 H 0.8208 -0.1343 0.0885 0.052 Uiso 1 1 calc R . . C16 C 0.8804(4) -0.0027(6) 0.1755(4) 0.0422(17) Uani 1 1 d . . . H16 H 0.9075 -0.0653 0.2155 0.051 Uiso 1 1 calc R . . C17 C 0.7263(4) -0.0047(6) -0.0431(4) 0.0329(15) Uani 1 1 d . . . C18 C 0.6589(4) 0.0672(7) -0.0930(4) 0.0401(17) Uani 1 1 d . . . H18 H 0.6497 0.1484 -0.0752 0.048 Uiso 1 1 calc R . . C19 C 0.6046(4) 0.0233(7) -0.1681(4) 0.0448(18) Uani 1 1 d . . . H19 H 0.5605 0.0760 -0.2006 0.054 Uiso 1 1 calc R . . C20 C 0.6147(4) -0.0995(6) -0.1961(4) 0.0357(16) Uani 1 1 d . . . C21 C 0.6826(4) -0.1727(7) -0.1467(4) 0.0503(19) Uani 1 1 d . . . H21 H 0.6914 -0.2546 -0.1639 0.060 Uiso 1 1 calc R . . C22 C 0.7374(4) -0.1249(7) -0.0718(4) 0.050(2) Uani 1 1 d . . . H22 H 0.7830 -0.1751 -0.0400 0.059 Uiso 1 1 calc R . . C23 C 0.4743(4) -0.1229(6) -0.2986(4) 0.0352(16) Uani 1 1 d . . . C24 C 0.4391(5) -0.1417(7) -0.2490(4) 0.0509(19) Uani 1 1 d . . . H24 H 0.4705 -0.1672 -0.1958 0.061 Uiso 1 1 calc R . . C25 C 0.3577(5) -0.1227(8) -0.2785(5) 0.058(2) Uani 1 1 d . . . H25 H 0.3337 -0.1322 -0.2450 0.069 Uiso 1 1 calc R . . C26 C 0.3114(5) -0.0892(8) -0.3580(6) 0.061(2) Uani 1 1 d . . . H26 H 0.2555 -0.0802 -0.3800 0.073 Uiso 1 1 calc R . . C27 C 0.3502(4) -0.0698(7) -0.4035(4) 0.0482(19) Uani 1 1 d . . . H27 H 0.3193 -0.0448 -0.4569 0.058 Uiso 1 1 calc R . . C28 C 0.5782(4) -0.2373(7) -0.3168(4) 0.0390(17) Uani 1 1 d . . . C29 C 0.6499(5) -0.2288(8) -0.3208(5) 0.062(2) Uani 1 1 d . . . H29 H 0.6859 -0.1597 -0.2958 0.074 Uiso 1 1 calc R . . C30 C 0.6673(5) -0.3248(10) -0.3625(6) 0.081(3) Uani 1 1 d . . . H30 H 0.7165 -0.3236 -0.3641 0.098 Uiso 1 1 calc R . . C31 C 0.6125(5) -0.4207(9) -0.4011(5) 0.069(3) Uani 1 1 d . . . H31 H 0.6225 -0.4853 -0.4307 0.083 Uiso 1 1 calc R . . C32 C 0.5421(5) -0.4205(8) -0.3956(5) 0.064(2) Uani 1 1 d . . . H32 H 0.5039 -0.4857 -0.4234 0.077 Uiso 1 1 calc R . . Cu1 Cu 1.01598(6) 0.06151(11) 0.45018(5) 0.0625(3) Uani 1 1 d . . . Cu2 Cu 0.48089(6) -0.03855(10) -0.44638(5) 0.0544(3) Uani 1 1 d . . . I1 I 1.10758(3) 0.10321(6) 0.60006(3) 0.0636(2) Uani 1 1 d . . . I2 I 0.58803(4) 0.14237(6) -0.41224(3) 0.0691(2) Uani 1 1 d . . . N1 N 0.9715(4) 0.2714(7) 0.3918(4) 0.077(2) Uani 1 1 d . . . N2 N 0.9478(3) 0.1691(5) 0.2733(3) 0.0380(13) Uani 1 1 d . . . N3 N 1.0670(3) 0.0709(5) 0.3761(3) 0.0398(14) Uani 1 1 d . . . N4 N 0.4312(3) -0.0847(5) -0.3753(3) 0.0372(13) Uani 1 1 d . . . N5 N 0.5574(3) -0.1453(5) -0.2728(3) 0.0382(13) Uani 1 1 d . . . N6 N 0.5243(3) -0.3320(6) -0.3526(3) 0.0477(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.082(7) 0.119(9) 0.063(6) -0.048(6) 0.007(5) 0.030(6) C2 0.091(8) 0.099(8) 0.077(7) -0.015(6) 0.048(6) 0.040(6) C3 0.054(5) 0.101(8) 0.088(7) -0.016(6) 0.037(5) 0.011(5) C4 0.040(5) 0.097(7) 0.055(5) -0.023(5) 0.018(4) 0.000(5) C5 0.032(4) 0.043(4) 0.035(4) 0.001(3) 0.014(3) 0.000(3) C6 0.037(4) 0.037(4) 0.034(4) -0.010(3) 0.018(3) -0.005(3) C7 0.042(4) 0.064(5) 0.039(4) -0.005(4) 0.022(4) -0.014(4) C8 0.051(5) 0.086(6) 0.060(6) -0.018(5) 0.035(5) -0.019(5) C9 0.032(4) 0.071(6) 0.066(6) -0.001(5) 0.018(4) 0.006(4) C10 0.040(5) 0.070(6) 0.047(5) 0.009(4) 0.017(4) 0.012(4) C11 0.033(4) 0.035(4) 0.030(4) 0.004(3) 0.011(3) 0.004(3) C12 0.108(7) 0.037(5) 0.034(4) -0.001(4) 0.000(4) 0.005(5) C13 0.094(7) 0.037(5) 0.037(4) 0.006(4) 0.005(4) 0.004(4) C14 0.035(4) 0.040(4) 0.027(4) 0.004(3) 0.011(3) 0.003(3) C15 0.043(4) 0.034(4) 0.043(4) -0.002(3) 0.010(4) -0.004(3) C16 0.041(4) 0.034(4) 0.038(4) 0.012(3) 0.007(3) 0.004(3) C17 0.041(4) 0.029(4) 0.030(4) -0.002(3) 0.017(3) -0.004(3) C18 0.043(4) 0.030(4) 0.036(4) -0.002(3) 0.008(3) 0.004(3) C19 0.048(4) 0.040(4) 0.040(4) 0.004(3) 0.015(4) 0.004(3) C20 0.034(4) 0.040(4) 0.031(4) -0.002(3) 0.014(3) 0.004(3) C21 0.057(5) 0.039(4) 0.048(5) -0.013(4) 0.019(4) 0.004(4) C22 0.040(4) 0.052(5) 0.035(4) -0.001(4) -0.001(3) 0.009(4) C23 0.037(4) 0.033(4) 0.040(4) -0.008(3) 0.021(3) -0.009(3) C24 0.059(5) 0.059(5) 0.041(4) -0.006(4) 0.028(4) -0.009(4) C25 0.057(5) 0.061(5) 0.081(6) -0.014(5) 0.054(5) -0.016(4) C26 0.039(5) 0.061(5) 0.086(7) -0.009(5) 0.032(5) -0.001(4) C27 0.042(5) 0.040(4) 0.055(5) 0.002(3) 0.015(4) 0.005(3) C28 0.034(4) 0.050(5) 0.029(4) 0.000(3) 0.011(3) -0.002(3) C29 0.048(5) 0.079(6) 0.068(5) -0.032(5) 0.036(4) -0.018(4) C30 0.057(6) 0.115(8) 0.087(7) -0.029(6) 0.045(5) -0.006(6) C31 0.072(6) 0.079(6) 0.068(6) -0.032(5) 0.041(5) 0.005(5) C32 0.064(6) 0.064(6) 0.054(5) -0.018(4) 0.019(4) -0.005(5) Cu1 0.0530(6) 0.0982(9) 0.0404(6) 0.0187(5) 0.0253(5) 0.0122(6) Cu2 0.0584(6) 0.0672(7) 0.0446(6) 0.0045(5) 0.0299(5) -0.0026(5) I1 0.0555(4) 0.0867(5) 0.0447(3) -0.0038(3) 0.0198(3) -0.0072(3) I2 0.0810(4) 0.0775(4) 0.0578(4) -0.0230(3) 0.0398(3) -0.0324(3) N1 0.060(4) 0.095(6) 0.054(4) -0.029(4) 0.008(4) 0.023(4) N2 0.035(3) 0.048(4) 0.023(3) -0.003(3) 0.007(3) 0.005(3) N3 0.037(3) 0.048(4) 0.036(3) 0.004(3) 0.018(3) 0.001(3) N4 0.038(3) 0.036(3) 0.039(3) -0.004(3) 0.019(3) -0.003(3) N5 0.034(3) 0.048(3) 0.029(3) -0.011(3) 0.011(3) -0.002(3) N6 0.045(4) 0.049(4) 0.049(4) -0.011(3) 0.021(3) -0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.331(12) . ? C1 N1 1.359(10) . ? C1 H1 0.9300 . ? C2 C3 1.355(12) . ? C2 H2 0.9300 . ? C3 C4 1.356(11) . ? C3 H3 0.9300 . ? C4 C5 1.366(9) . ? C4 H4 0.9300 . ? C5 N1 1.311(8) . ? C5 N2 1.406(8) . ? C6 N3 1.337(8) . ? C6 C7 1.392(9) . ? C6 N2 1.414(8) . ? C7 C8 1.348(10) . ? C7 H7 0.9300 . ? C8 C9 1.374(11) . ? C8 H8 0.9300 . ? C9 C10 1.361(10) . ? C9 H9 0.9300 . ? C10 N3 1.338(8) . ? C10 H10 0.9300 . ? C11 C16 1.358(9) . ? C11 C12 1.385(9) . ? C11 N2 1.426(8) . ? C12 C13 1.373(10) . ? C12 H12 0.9300 . ? C13 C14 1.390(9) . ? C13 H13 0.9300 . ? C14 C15 1.365(9) . ? C14 C17 1.479(9) . ? C15 C16 1.376(9) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.374(9) . ? C17 C22 1.381(9) . ? C18 C19 1.372(8) . ? C18 H18 0.9300 . ? C19 C20 1.393(9) . ? C19 H19 0.9300 . ? C20 C21 1.384(9) . ? C20 N5 1.415(8) . ? C21 C22 1.385(9) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 N4 1.340(8) . ? C23 C24 1.378(9) . ? C23 N5 1.408(8) . ? C24 C25 1.365(10) . ? C24 H24 0.9300 . ? C25 C26 1.375(11) . ? C25 H25 0.9300 . ? C26 C27 1.365(10) . ? C26 H26 0.9300 . ? C27 N4 1.355(8) . ? C27 H27 0.9300 . ? C28 N6 1.322(8) . ? C28 C29 1.374(9) . ? C28 N5 1.412(8) . ? C29 C30 1.376(11) . ? C29 H29 0.9300 . ? C30 C31 1.348(11) . ? C30 H30 0.9300 . ? C31 C32 1.361(11) . ? C31 H31 0.9300 . ? C32 N6 1.344(9) . ? C32 H32 0.9300 . ? Cu1 N3 2.017(5) . ? Cu1 N1 2.352(8) . ? Cu1 Cu1 2.5348(18) 3_756 ? Cu1 I1 2.5592(11) . ? Cu1 I1 2.6334(12) 3_756 ? Cu2 N4 1.999(5) . ? Cu2 Cu2 2.5480(17) 3_654 ? Cu2 I2 2.5572(11) . ? Cu2 I2 2.5746(11) 3_654 ? I1 Cu1 2.6334(12) 3_756 ? I2 Cu2 2.5746(11) 3_654 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N1 125.9(8) . . ? C2 C1 H1 117.0 . . ? N1 C1 H1 117.0 . . ? C1 C2 C3 115.4(8) . . ? C1 C2 H2 122.3 . . ? C3 C2 H2 122.3 . . ? C2 C3 C4 121.2(8) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 119.3(8) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 C4 121.4(7) . . ? N1 C5 N2 115.7(6) . . ? C4 C5 N2 122.8(6) . . ? N3 C6 C7 121.8(6) . . ? N3 C6 N2 119.7(6) . . ? C7 C6 N2 118.5(6) . . ? C8 C7 C6 119.2(7) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 119.5(7) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 118.4(7) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? N3 C10 C9 123.5(7) . . ? N3 C10 H10 118.2 . . ? C9 C10 H10 118.2 . . ? C16 C11 C12 117.8(6) . . ? C16 C11 N2 119.9(6) . . ? C12 C11 N2 122.1(6) . . ? C13 C12 C11 120.8(7) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 121.5(7) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C15 C14 C13 116.1(6) . . ? C15 C14 C17 121.6(6) . . ? C13 C14 C17 122.3(6) . . ? C14 C15 C16 122.8(6) . . ? C14 C15 H15 118.6 . . ? C16 C15 H15 118.6 . . ? C11 C16 C15 120.8(6) . . ? C11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C18 C17 C22 116.9(6) . . ? C18 C17 C14 122.4(6) . . ? C22 C17 C14 120.6(6) . . ? C19 C18 C17 122.3(6) . . ? C19 C18 H18 118.9 . . ? C17 C18 H18 118.9 . . ? C18 C19 C20 120.7(6) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C21 C20 C19 117.6(6) . . ? C21 C20 N5 122.1(6) . . ? C19 C20 N5 120.3(6) . . ? C20 C21 C22 120.6(6) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C17 C22 C21 121.9(6) . . ? C17 C22 H22 119.1 . . ? C21 C22 H22 119.1 . . ? N4 C23 C24 122.0(6) . . ? N4 C23 N5 115.6(5) . . ? C24 C23 N5 122.5(6) . . ? C25 C24 C23 119.6(7) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 119.6(7) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C27 C26 C25 117.9(7) . . ? C27 C26 H26 121.1 . . ? C25 C26 H26 121.1 . . ? N4 C27 C26 123.8(7) . . ? N4 C27 H27 118.1 . . ? C26 C27 H27 118.1 . . ? N6 C28 C29 123.1(7) . . ? N6 C28 N5 115.0(6) . . ? C29 C28 N5 121.9(6) . . ? C28 C29 C30 118.5(8) . . ? C28 C29 H29 120.7 . . ? C30 C29 H29 120.7 . . ? C31 C30 C29 119.5(8) . . ? C31 C30 H30 120.3 . . ? C29 C30 H30 120.3 . . ? C30 C31 C32 118.3(8) . . ? C30 C31 H31 120.8 . . ? C32 C31 H31 120.8 . . ? N6 C32 C31 124.1(8) . . ? N6 C32 H32 118.0 . . ? C31 C32 H32 118.0 . . ? N3 Cu1 N1 79.2(2) . . ? N3 Cu1 Cu1 151.44(17) . 3_756 ? N1 Cu1 Cu1 129.24(19) . 3_756 ? N3 Cu1 I1 117.57(16) . . ? N1 Cu1 I1 105.99(16) . . ? Cu1 Cu1 I1 62.25(4) 3_756 . ? N3 Cu1 I1 113.30(16) . 3_756 ? N1 Cu1 I1 109.94(17) . 3_756 ? Cu1 Cu1 I1 59.33(4) 3_756 3_756 ? I1 Cu1 I1 121.58(4) . 3_756 ? N4 Cu2 Cu2 169.55(17) . 3_654 ? N4 Cu2 I2 123.22(15) . . ? Cu2 Cu2 I2 60.57(4) 3_654 . ? N4 Cu2 I2 115.41(15) . 3_654 ? Cu2 Cu2 I2 59.89(4) 3_654 3_654 ? I2 Cu2 I2 120.46(3) . 3_654 ? Cu1 I1 Cu1 58.42(4) . 3_756 ? Cu2 I2 Cu2 59.54(3) . 3_654 ? C5 N1 C1 116.5(7) . . ? C5 N1 Cu1 103.4(5) . . ? C1 N1 Cu1 112.1(7) . . ? C5 N2 C6 124.3(5) . . ? C5 N2 C11 119.4(5) . . ? C6 N2 C11 116.3(5) . . ? C6 N3 C10 117.4(6) . . ? C6 N3 Cu1 122.0(4) . . ? C10 N3 Cu1 120.3(5) . . ? C23 N4 C27 117.1(6) . . ? C23 N4 Cu2 123.5(4) . . ? C27 N4 Cu2 119.3(5) . . ? C23 N5 C28 117.4(5) . . ? C23 N5 C20 119.2(5) . . ? C28 N5 C20 121.9(5) . . ? C28 N6 C32 116.4(6) . . ? 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 6.0(18) . . . . ? C1 C2 C3 C4 -4.1(16) . . . . ? C2 C3 C4 C5 -0.5(15) . . . . ? C3 C4 C5 N1 3.9(13) . . . . ? C3 C4 C5 N2 -176.5(7) . . . . ? N3 C6 C7 C8 1.3(10) . . . . ? N2 C6 C7 C8 -178.2(6) . . . . ? C6 C7 C8 C9 -1.7(11) . . . . ? C7 C8 C9 C10 0.8(12) . . . . ? C8 C9 C10 N3 0.7(13) . . . . ? C16 C11 C12 C13 4.5(12) . . . . ? N2 C11 C12 C13 -178.8(8) . . . . ? C11 C12 C13 C14 -1.3(14) . . . . ? C12 C13 C14 C15 -2.9(12) . . . . ? C12 C13 C14 C17 178.6(8) . . . . ? C13 C14 C15 C16 4.0(11) . . . . ? C17 C14 C15 C16 -177.5(6) . . . . ? C12 C11 C16 C15 -3.5(11) . . . . ? N2 C11 C16 C15 179.8(6) . . . . ? C14 C15 C16 C11 -0.9(11) . . . . ? C15 C14 C17 C18 149.7(7) . . . . ? C13 C14 C17 C18 -32.0(10) . . . . ? C15 C14 C17 C22 -30.3(10) . . . . ? C13 C14 C17 C22 148.0(8) . . . . ? C22 C17 C18 C19 -0.1(10) . . . . ? C14 C17 C18 C19 179.9(6) . . . . ? C17 C18 C19 C20 1.8(11) . . . . ? C18 C19 C20 C21 -2.1(10) . . . . ? C18 C19 C20 N5 178.4(6) . . . . ? C19 C20 C21 C22 0.7(11) . . . . ? N5 C20 C21 C22 -179.8(6) . . . . ? C18 C17 C22 C21 -1.3(11) . . . . ? C14 C17 C22 C21 178.7(7) . . . . ? C20 C21 C22 C17 1.0(12) . . . . ? N4 C23 C24 C25 0.8(10) . . . . ? N5 C23 C24 C25 -177.7(6) . . . . ? C23 C24 C25 C26 2.1(11) . . . . ? C24 C25 C26 C27 -3.3(12) . . . . ? C25 C26 C27 N4 1.7(12) . . . . ? N6 C28 C29 C30 -1.4(12) . . . . ? N5 C28 C29 C30 177.7(7) . . . . ? C28 C29 C30 C31 2.9(14) . . . . ? C29 C30 C31 C32 -1.5(15) . . . . ? C30 C31 C32 N6 -1.5(14) . . . . ? N3 Cu1 I1 Cu1 -147.7(2) . . . 3_756 ? N1 Cu1 I1 Cu1 126.3(2) . . . 3_756 ? I1 Cu1 I1 Cu1 0.0 3_756 . . 3_756 ? N4 Cu2 I2 Cu2 -168.6(2) . . . 3_654 ? I2 Cu2 I2 Cu2 0.0 3_654 . . 3_654 ? C4 C5 N1 C1 -2.4(13) . . . . ? N2 C5 N1 C1 178.0(8) . . . . ? C4 C5 N1 Cu1 121.0(7) . . . . ? N2 C5 N1 Cu1 -58.6(7) . . . . ? C2 C1 N1 C5 -2.8(17) . . . . ? C2 C1 N1 Cu1 -121.6(11) . . . . ? N3 Cu1 N1 C5 70.7(5) . . . . ? Cu1 Cu1 N1 C5 -106.5(5) 3_756 . . . ? I1 Cu1 N1 C5 -173.5(4) . . . . ? I1 Cu1 N1 C5 -40.3(5) 3_756 . . . ? N3 Cu1 N1 C1 -163.0(7) . . . . ? Cu1 Cu1 N1 C1 19.8(7) 3_756 . . . ? I1 Cu1 N1 C1 -47.2(6) . . . . ? I1 Cu1 N1 C1 85.9(6) 3_756 . . . ? N1 C5 N2 C6 -1.4(10) . . . . ? C4 C5 N2 C6 179.0(7) . . . . ? N1 C5 N2 C11 176.6(6) . . . . ? C4 C5 N2 C11 -3.0(10) . . . . ? N3 C6 N2 C5 46.8(9) . . . . ? C7 C6 N2 C5 -133.6(7) . . . . ? N3 C6 N2 C11 -131.2(6) . . . . ? C7 C6 N2 C11 48.3(8) . . . . ? C16 C11 N2 C5 -117.7(7) . . . . ? C12 C11 N2 C5 65.7(9) . . . . ? C16 C11 N2 C6 60.4(8) . . . . ? C12 C11 N2 C6 -116.1(8) . . . . ? C7 C6 N3 C10 0.1(10) . . . . ? N2 C6 N3 C10 179.6(6) . . . . ? C7 C6 N3 Cu1 174.0(5) . . . . ? N2 C6 N3 Cu1 -6.5(8) . . . . ? C9 C10 N3 C6 -1.1(11) . . . . ? C9 C10 N3 Cu1 -175.1(6) . . . . ? N1 Cu1 N3 C6 -37.4(5) . . . . ? Cu1 Cu1 N3 C6 138.1(4) 3_756 . . . ? I1 Cu1 N3 C6 -139.9(4) . . . . ? I1 Cu1 N3 C6 69.8(5) 3_756 . . . ? N1 Cu1 N3 C10 136.3(6) . . . . ? Cu1 Cu1 N3 C10 -48.2(7) 3_756 . . . ? I1 Cu1 N3 C10 33.8(6) . . . . ? I1 Cu1 N3 C10 -116.5(5) 3_756 . . . ? C24 C23 N4 C27 -2.4(9) . . . . ? N5 C23 N4 C27 176.2(6) . . . . ? C24 C23 N4 Cu2 173.7(5) . . . . ? N5 C23 N4 Cu2 -7.8(8) . . . . ? C26 C27 N4 C23 1.1(10) . . . . ? C26 C27 N4 Cu2 -175.1(6) . . . . ? Cu2 Cu2 N4 C23 -165.7(7) 3_654 . . . ? I2 Cu2 N4 C23 -57.5(5) . . . . ? I2 Cu2 N4 C23 133.4(4) 3_654 . . . ? Cu2 Cu2 N4 C27 10.3(13) 3_654 . . . ? I2 Cu2 N4 C27 118.5(5) . . . . ? I2 Cu2 N4 C27 -50.6(5) 3_654 . . . ? N4 C23 N5 C28 -55.9(8) . . . . ? C24 C23 N5 C28 122.7(7) . . . . ? N4 C23 N5 C20 137.7(6) . . . . ? C24 C23 N5 C20 -43.7(9) . . . . ? N6 C28 N5 C23 -28.5(8) . . . . ? C29 C28 N5 C23 152.4(7) . . . . ? N6 C28 N5 C20 137.5(6) . . . . ? C29 C28 N5 C20 -41.6(10) . . . . ? C21 C20 N5 C23 140.8(7) . . . . ? C19 C20 N5 C23 -39.7(9) . . . . ? C21 C20 N5 C28 -25.0(10) . . . . ? C19 C20 N5 C28 154.5(6) . . . . ? C29 C28 N6 C32 -1.5(11) . . . . ? N5 C28 N6 C32 179.5(6) . . . . ? C31 C32 N6 C28 2.9(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.558 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.129 data_1 _database_code_depnum_ccdc_archive 'CCDC 773756' #TrackingRef '- 1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H19 Cu2 I2 N7' _chemical_formula_weight 798.35 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.6328(11) _cell_length_b 22.983(3) _cell_length_c 14.1392(17) _cell_angle_alpha 90.00 _cell_angle_beta 91.257(2) _cell_angle_gamma 90.00 _cell_volume 2804.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.891 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_absorpt_coefficient_mu 3.745 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6035 _exptl_absorpt_correction_T_max 0.6222 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _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 APEX area-dectector diffractometer' _diffrn_measurement_method '\f and \w-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15066 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4932 _reflns_number_gt 3928 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material SHELXL-97 _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^)+(0.0491P)^2^+0.9097P] 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 4932 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0924 _refine_ls_wR_factor_gt 0.0852 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1051(6) 0.3606(3) 0.9653(4) 0.0565(14) Uani 1 1 d . . . H1 H 0.0194 0.3767 0.9942 0.068 Uiso 1 1 calc R . . C2 C 0.0834(7) 0.3351(3) 0.8794(4) 0.0671(16) Uani 1 1 d . . . H2 H -0.0147 0.3330 0.8510 0.081 Uiso 1 1 calc R . . C3 C 0.2106(8) 0.3125(3) 0.8356(4) 0.0703(18) Uani 1 1 d . . . H3 H 0.1992 0.2943 0.7772 0.084 Uiso 1 1 calc R . . C4 C 0.3543(7) 0.3168(2) 0.8780(4) 0.0557(14) Uani 1 1 d . . . H4 H 0.4419 0.3029 0.8483 0.067 Uiso 1 1 calc R . . C5 C 0.3652(5) 0.3427(2) 0.9665(3) 0.0382(11) Uani 1 1 d . . . C6 C 0.5538(5) 0.4042(2) 1.0524(3) 0.0371(11) Uani 1 1 d . . . C7 C 0.6654(6) 0.4376(2) 1.0091(4) 0.0477(12) Uani 1 1 d . . . H7 H 0.7092 0.4251 0.9531 0.057 Uiso 1 1 calc R . . C8 C 0.7108(6) 0.4890(2) 1.0495(4) 0.0554(14) Uani 1 1 d . . . H8 H 0.7872 0.5115 1.0220 0.066 Uiso 1 1 calc R . . C9 C 0.6423(6) 0.5071(2) 1.1308(4) 0.0514(13) Uani 1 1 d . . . H9 H 0.6726 0.5416 1.1602 0.062 Uiso 1 1 calc R . . C10 C 0.5268(6) 0.4727(2) 1.1684(4) 0.0484(13) Uani 1 1 d . . . H10 H 0.4774 0.4858 1.2222 0.058 Uiso 1 1 calc R . . C11 C 0.6025(5) 0.3008(2) 1.0372(3) 0.0378(11) Uani 1 1 d . . . C12 C 0.7478(5) 0.3059(2) 1.0798(4) 0.0463(12) Uani 1 1 d . . . H12 H 0.7904 0.3421 1.0943 0.056 Uiso 1 1 calc R . . C13 C 0.8266(6) 0.2549(2) 1.0997(4) 0.0520(13) Uani 1 1 d . . . H13 H 0.9244 0.2566 1.1284 0.062 Uiso 1 1 calc R . . C14 C 0.7621(6) 0.2015(2) 1.0774(3) 0.0469(12) Uani 1 1 d . . . H14 H 0.8139 0.1669 1.0910 0.056 Uiso 1 1 calc R . . C15 C 0.6164(5) 0.2017(2) 1.0340(3) 0.0357(10) Uani 1 1 d . . . C16 C 0.3974(5) 0.1524(2) 0.9553(3) 0.0384(11) Uani 1 1 d . . . C17 C 0.2625(6) 0.1731(2) 0.9945(4) 0.0554(14) Uani 1 1 d . . . H17 H 0.2624 0.1868 1.0564 0.067 Uiso 1 1 calc R . . C18 C 0.1302(6) 0.1730(3) 0.9404(5) 0.0690(17) Uani 1 1 d . . . H18 H 0.0387 0.1874 0.9649 0.083 Uiso 1 1 calc R . . C19 C 0.1316(6) 0.1516(2) 0.8499(5) 0.0623(16) Uani 1 1 d . . . H19 H 0.0418 0.1508 0.8124 0.075 Uiso 1 1 calc R . . C20 C 0.2679(6) 0.1317(2) 0.8169(4) 0.0508(13) Uani 1 1 d . . . H20 H 0.2689 0.1167 0.7558 0.061 Uiso 1 1 calc R . . C21 C 0.6204(5) 0.0963(2) 1.0154(3) 0.0395(11) Uani 1 1 d . . . C22 C 0.6203(6) 0.0654(2) 1.0981(4) 0.0546(14) Uani 1 1 d . . . H22 H 0.5655 0.0789 1.1495 0.066 Uiso 1 1 calc R . . C23 C 0.7016(7) 0.0140(3) 1.1045(4) 0.0648(16) Uani 1 1 d . . . H23 H 0.7045 -0.0072 1.1605 0.078 Uiso 1 1 calc R . . C24 C 0.7783(7) -0.0053(2) 1.0267(4) 0.0594(15) Uani 1 1 d . . . H24 H 0.8343 -0.0399 1.0286 0.071 Uiso 1 1 calc R . . C25 C 0.7700(6) 0.0277(2) 0.9459(4) 0.0590(15) Uani 1 1 d . . . H25 H 0.8209 0.0141 0.8929 0.071 Uiso 1 1 calc R . . Cu1 Cu 0.76711(7) 0.11622(3) 0.65452(4) 0.04769(18) Uani 1 1 d . . . Cu2 Cu 0.61758(7) 0.11484(3) 0.81000(4) 0.05055(19) Uani 1 1 d . . . I1 I 0.73659(4) 0.211737(15) 0.75076(2) 0.05005(12) Uani 1 1 d . . . I2 I 0.58351(4) 0.027193(17) 0.69083(3) 0.05938(14) Uani 1 1 d . . . N1 N 0.2430(4) 0.36389(17) 1.0111(3) 0.0418(9) Uani 1 1 d . . . N2 N 0.5115(4) 0.34950(17) 1.0145(3) 0.0414(9) Uani 1 1 d . . . N3 N 0.4829(4) 0.42154(16) 1.1306(3) 0.0387(9) Uani 1 1 d . . . N4 N 0.5378(4) 0.24984(16) 1.0150(2) 0.0375(9) Uani 1 1 d . . . N5 N 0.4020(4) 0.13240(16) 0.8674(3) 0.0399(9) Uani 1 1 d . . . N6 N 0.5401(4) 0.14994(16) 1.0085(3) 0.0423(9) Uani 1 1 d . . . N7 N 0.6938(4) 0.07816(18) 0.9383(3) 0.0451(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 C1 0.044(3) 0.074(4) 0.051(3) -0.002(3) -0.003(3) -0.004(3) C2 0.056(4) 0.084(5) 0.060(4) -0.005(3) -0.022(3) -0.004(3) C3 0.086(5) 0.080(4) 0.044(3) -0.014(3) -0.018(3) 0.014(4) C4 0.062(4) 0.063(4) 0.041(3) -0.010(3) 0.000(3) 0.012(3) C5 0.040(3) 0.037(3) 0.038(3) -0.001(2) 0.001(2) 0.001(2) C6 0.032(2) 0.041(3) 0.039(3) 0.002(2) 0.003(2) 0.004(2) C7 0.041(3) 0.053(3) 0.049(3) 0.003(2) 0.006(2) -0.004(2) C8 0.042(3) 0.061(4) 0.063(4) 0.019(3) -0.004(3) -0.014(3) C9 0.053(3) 0.038(3) 0.063(4) 0.006(3) -0.015(3) -0.011(2) C10 0.051(3) 0.047(3) 0.047(3) -0.009(2) -0.005(2) 0.001(2) C11 0.038(3) 0.043(3) 0.032(3) -0.004(2) 0.012(2) 0.003(2) C12 0.037(3) 0.049(3) 0.053(3) -0.011(2) 0.002(2) -0.001(2) C13 0.039(3) 0.066(4) 0.050(3) -0.004(3) -0.010(2) 0.001(3) C14 0.046(3) 0.049(3) 0.046(3) -0.003(2) -0.003(2) 0.010(2) C15 0.037(3) 0.040(3) 0.030(2) -0.0065(19) 0.0061(19) 0.003(2) C16 0.035(3) 0.038(3) 0.042(3) -0.002(2) 0.003(2) 0.001(2) C17 0.048(3) 0.055(4) 0.064(4) -0.015(3) 0.012(3) 0.005(3) C18 0.039(3) 0.067(4) 0.101(5) -0.009(4) 0.011(3) 0.009(3) C19 0.040(3) 0.062(4) 0.084(5) 0.000(3) -0.021(3) 0.011(3) C20 0.050(3) 0.052(3) 0.049(3) 0.001(2) -0.011(3) 0.003(3) C21 0.037(3) 0.044(3) 0.037(3) 0.000(2) -0.002(2) -0.002(2) C22 0.064(4) 0.057(4) 0.043(3) 0.002(3) 0.008(3) 0.007(3) C23 0.077(4) 0.060(4) 0.058(4) 0.020(3) 0.000(3) 0.003(3) C24 0.067(4) 0.041(3) 0.071(4) 0.012(3) -0.006(3) 0.014(3) C25 0.056(4) 0.064(4) 0.057(4) -0.005(3) 0.006(3) 0.022(3) Cu1 0.0462(4) 0.0579(4) 0.0393(4) 0.0019(3) 0.0099(3) 0.0040(3) Cu2 0.0485(4) 0.0624(4) 0.0411(4) 0.0056(3) 0.0106(3) 0.0066(3) I1 0.0476(2) 0.0445(2) 0.0580(2) -0.00001(16) -0.00042(16) 0.00506(15) I2 0.0583(2) 0.0681(3) 0.0524(2) -0.01133(17) 0.01614(18) -0.02040(18) N1 0.039(2) 0.049(3) 0.038(2) -0.0003(18) -0.0002(18) -0.0011(18) N2 0.035(2) 0.041(2) 0.049(3) -0.0086(19) -0.0002(18) 0.0060(18) N3 0.037(2) 0.040(2) 0.039(2) -0.0001(18) 0.0020(17) -0.0025(17) N4 0.037(2) 0.041(2) 0.034(2) -0.0056(17) 0.0021(17) 0.0024(18) N5 0.035(2) 0.042(2) 0.042(2) 0.0030(18) 0.0012(18) 0.0023(17) N6 0.042(2) 0.038(2) 0.046(2) -0.0073(18) -0.0031(18) 0.0061(18) N7 0.044(2) 0.052(3) 0.040(2) 0.0048(19) 0.0058(18) 0.015(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.344(6) . ? C1 C2 1.358(7) . ? C1 H1 0.9300 . ? C2 C3 1.375(8) . ? C2 H2 0.9300 . ? C3 C4 1.369(8) . ? C3 H3 0.9300 . ? C4 C5 1.387(7) . ? C4 H4 0.9300 . ? C5 N1 1.333(6) . ? C5 N2 1.428(6) . ? C6 N3 1.337(5) . ? C6 C7 1.385(6) . ? C6 N2 1.411(6) . ? C7 C8 1.367(7) . ? C7 H7 0.9300 . ? C8 C9 1.369(8) . ? C8 H8 0.9300 . ? C9 C10 1.386(7) . ? C9 H9 0.9300 . ? C10 N3 1.343(6) . ? C10 H10 0.9300 . ? C11 N4 1.331(6) . ? C11 C12 1.385(7) . ? C11 N2 1.401(6) . ? C12 C13 1.381(7) . ? C12 H12 0.9300 . ? C13 C14 1.383(7) . ? C13 H13 0.9300 . ? C14 C15 1.387(7) . ? C14 H14 0.9300 . ? C15 N4 1.322(5) . ? C15 N6 1.403(6) . ? C16 N5 1.326(6) . ? C16 C17 1.385(6) . ? C16 N6 1.430(6) . ? C17 C18 1.361(8) . ? C17 H17 0.9300 . ? C18 C19 1.371(8) . ? C18 H18 0.9300 . ? C19 C20 1.355(7) . ? C19 H19 0.9300 . ? C20 N5 1.347(6) . ? C20 H20 0.9300 . ? C21 N7 1.339(6) . ? C21 C22 1.369(7) . ? C21 N6 1.416(6) . ? C22 C23 1.375(8) . ? C22 H22 0.9300 . ? C23 C24 1.370(8) . ? C23 H23 0.9300 . ? C24 C25 1.373(8) . ? C24 H24 0.9300 . ? C25 N7 1.336(6) . ? C25 H25 0.9300 . ? Cu1 N1 2.085(4) 4_665 ? Cu1 N3 2.089(4) 4_665 ? Cu1 Cu2 2.5738(9) . ? Cu1 I1 2.5994(8) . ? Cu1 I2 2.6453(8) . ? Cu2 N5 2.086(4) . ? Cu2 N7 2.094(4) . ? Cu2 I1 2.5989(8) . ? Cu2 I2 2.6385(8) . ? N1 Cu1 2.085(4) 4_566 ? N3 Cu1 2.089(4) 4_566 ? 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 123.9(5) . . ? N1 C1 H1 118.0 . . ? C2 C1 H1 118.0 . . ? C1 C2 C3 118.0(5) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 120.0(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 118.0(5) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? N1 C5 C4 122.9(5) . . ? N1 C5 N2 115.9(4) . . ? C4 C5 N2 121.2(4) . . ? N3 C6 C7 122.4(4) . . ? N3 C6 N2 117.4(4) . . ? C7 C6 N2 120.2(4) . . ? C8 C7 C6 119.4(5) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 119.2(5) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C8 C9 C10 118.5(5) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? N3 C10 C9 123.0(5) . . ? N3 C10 H10 118.5 . . ? C9 C10 H10 118.5 . . ? N4 C11 C12 123.3(4) . . ? N4 C11 N2 114.7(4) . . ? C12 C11 N2 121.9(4) . . ? C13 C12 C11 116.9(5) . . ? C13 C12 H12 121.5 . . ? C11 C12 H12 121.5 . . ? C14 C13 C12 120.9(5) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 117.0(5) . . ? C13 C14 H14 121.5 . . ? C15 C14 H14 121.5 . . ? N4 C15 C14 123.3(4) . . ? N4 C15 N6 114.9(4) . . ? C14 C15 N6 121.7(4) . . ? N5 C16 C17 122.5(4) . . ? N5 C16 N6 115.9(4) . . ? C17 C16 N6 121.6(4) . . ? C18 C17 C16 118.5(5) . . ? C18 C17 H17 120.8 . . ? C16 C17 H17 120.8 . . ? C17 C18 C19 120.1(5) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C20 C19 C18 117.9(5) . . ? C20 C19 H19 121.0 . . ? C18 C19 H19 121.0 . . ? N5 C20 C19 123.8(5) . . ? N5 C20 H20 118.1 . . ? C19 C20 H20 118.1 . . ? N7 C21 C22 122.8(5) . . ? N7 C21 N6 117.1(4) . . ? C22 C21 N6 120.1(4) . . ? C21 C22 C23 119.5(5) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C24 C23 C22 118.8(5) . . ? C24 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? C23 C24 C25 118.1(5) . . ? C23 C24 H24 120.9 . . ? C25 C24 H24 120.9 . . ? N7 C25 C24 124.2(5) . . ? N7 C25 H25 117.9 . . ? C24 C25 H25 117.9 . . ? N1 Cu1 N3 90.24(15) 4_665 4_665 ? N1 Cu1 Cu2 142.39(11) 4_665 . ? N3 Cu1 Cu2 126.78(10) 4_665 . ? N1 Cu1 I1 108.36(11) 4_665 . ? N3 Cu1 I1 122.44(11) 4_665 . ? Cu2 Cu1 I1 60.31(2) . . ? N1 Cu1 I2 108.11(11) 4_665 . ? N3 Cu1 I2 104.50(11) 4_665 . ? Cu2 Cu1 I2 60.72(2) . . ? I1 Cu1 I2 118.92(2) . . ? N5 Cu2 N7 90.37(15) . . ? N5 Cu2 Cu1 142.98(11) . . ? N7 Cu2 Cu1 126.25(10) . . ? N5 Cu2 I1 108.78(11) . . ? N7 Cu2 I1 120.36(12) . . ? Cu1 Cu2 I1 60.33(2) . . ? N5 Cu2 I2 107.96(11) . . ? N7 Cu2 I2 105.94(12) . . ? Cu1 Cu2 I2 60.98(2) . . ? I1 Cu2 I2 119.19(3) . . ? Cu2 I1 Cu1 59.36(2) . . ? Cu2 I2 Cu1 58.30(2) . . ? C5 N1 C1 117.0(4) . . ? C5 N1 Cu1 118.4(3) . 4_566 ? C1 N1 Cu1 123.3(3) . 4_566 ? C11 N2 C6 119.1(4) . . ? C11 N2 C5 120.4(4) . . ? C6 N2 C5 119.8(4) . . ? C6 N3 C10 117.4(4) . . ? C6 N3 Cu1 115.8(3) . 4_566 ? C10 N3 Cu1 123.0(3) . 4_566 ? C15 N4 C11 118.5(4) . . ? C16 N5 C20 117.2(4) . . ? C16 N5 Cu2 118.5(3) . . ? C20 N5 Cu2 123.7(3) . . ? C15 N6 C21 119.6(4) . . ? C15 N6 C16 119.7(4) . . ? C21 N6 C16 119.0(4) . . ? C25 N7 C21 116.6(4) . . ? C25 N7 Cu2 124.3(3) . . ? C21 N7 Cu2 115.7(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -1.6(9) . . . . ? C1 C2 C3 C4 -0.9(9) . . . . ? C2 C3 C4 C5 2.1(9) . . . . ? C3 C4 C5 N1 -0.8(8) . . . . ? C3 C4 C5 N2 -179.1(5) . . . . ? N3 C6 C7 C8 2.9(8) . . . . ? N2 C6 C7 C8 -176.6(4) . . . . ? C6 C7 C8 C9 -1.4(8) . . . . ? C7 C8 C9 C10 -1.2(8) . . . . ? C8 C9 C10 N3 2.5(8) . . . . ? N4 C11 C12 C13 -0.3(7) . . . . ? N2 C11 C12 C13 179.5(4) . . . . ? C11 C12 C13 C14 0.2(7) . . . . ? C12 C13 C14 C15 0.5(7) . . . . ? C13 C14 C15 N4 -1.2(7) . . . . ? C13 C14 C15 N6 -179.9(4) . . . . ? N5 C16 C17 C18 -0.2(8) . . . . ? N6 C16 C17 C18 -178.5(5) . . . . ? C16 C17 C18 C19 1.2(9) . . . . ? C17 C18 C19 C20 -0.8(9) . . . . ? C18 C19 C20 N5 -0.8(9) . . . . ? N7 C21 C22 C23 1.8(8) . . . . ? N6 C21 C22 C23 -178.6(5) . . . . ? C21 C22 C23 C24 -1.3(9) . . . . ? C22 C23 C24 C25 0.0(9) . . . . ? C23 C24 C25 N7 1.0(10) . . . . ? N1 Cu1 Cu2 N5 0.4(3) 4_665 . . . ? N3 Cu1 Cu2 N5 -167.9(2) 4_665 . . . ? I1 Cu1 Cu2 N5 81.95(18) . . . . ? I2 Cu1 Cu2 N5 -81.37(18) . . . . ? N1 Cu1 Cu2 N7 170.7(2) 4_665 . . . ? N3 Cu1 Cu2 N7 2.5(2) 4_665 . . . ? I1 Cu1 Cu2 N7 -107.67(15) . . . . ? I2 Cu1 Cu2 N7 89.00(15) . . . . ? N1 Cu1 Cu2 I1 -81.60(19) 4_665 . . . ? N3 Cu1 Cu2 I1 110.17(13) 4_665 . . . ? I2 Cu1 Cu2 I1 -163.32(3) . . . . ? N1 Cu1 Cu2 I2 81.72(19) 4_665 . . . ? N3 Cu1 Cu2 I2 -86.51(13) 4_665 . . . ? I1 Cu1 Cu2 I2 163.32(3) . . . . ? N5 Cu2 I1 Cu1 -140.98(12) . . . . ? N7 Cu2 I1 Cu1 117.06(12) . . . . ? I2 Cu2 I1 Cu1 -16.71(3) . . . . ? N1 Cu1 I1 Cu2 140.50(11) 4_665 . . . ? N3 Cu1 I1 Cu2 -117.02(12) 4_665 . . . ? I2 Cu1 I1 Cu2 16.62(3) . . . . ? N5 Cu2 I2 Cu1 141.27(11) . . . . ? N7 Cu2 I2 Cu1 -123.01(11) . . . . ? I1 Cu2 I2 Cu1 16.60(3) . . . . ? N1 Cu1 I2 Cu2 -140.55(12) 4_665 . . . ? N3 Cu1 I2 Cu2 124.34(11) 4_665 . . . ? I1 Cu1 I2 Cu2 -16.55(3) . . . . ? C4 C5 N1 C1 -1.5(7) . . . . ? N2 C5 N1 C1 176.8(4) . . . . ? C4 C5 N1 Cu1 166.1(4) . . . 4_566 ? N2 C5 N1 Cu1 -15.6(5) . . . 4_566 ? C2 C1 N1 C5 2.8(8) . . . . ? C2 C1 N1 Cu1 -164.2(5) . . . 4_566 ? N4 C11 N2 C6 166.9(4) . . . . ? C12 C11 N2 C6 -12.9(6) . . . . ? N4 C11 N2 C5 -3.2(6) . . . . ? C12 C11 N2 C5 177.0(4) . . . . ? N3 C6 N2 C11 -96.6(5) . . . . ? C7 C6 N2 C11 83.0(5) . . . . ? N3 C6 N2 C5 73.5(5) . . . . ? C7 C6 N2 C5 -106.9(5) . . . . ? N1 C5 N2 C11 121.8(5) . . . . ? C4 C5 N2 C11 -59.8(6) . . . . ? N1 C5 N2 C6 -48.2(6) . . . . ? C4 C5 N2 C6 130.1(5) . . . . ? C7 C6 N3 C10 -1.7(7) . . . . ? N2 C6 N3 C10 177.9(4) . . . . ? C7 C6 N3 Cu1 157.1(4) . . . 4_566 ? N2 C6 N3 Cu1 -23.4(5) . . . 4_566 ? C9 C10 N3 C6 -1.1(7) . . . . ? C9 C10 N3 Cu1 -158.2(4) . . . 4_566 ? C14 C15 N4 C11 1.1(7) . . . . ? N6 C15 N4 C11 179.9(4) . . . . ? C12 C11 N4 C15 -0.3(7) . . . . ? N2 C11 N4 C15 179.9(4) . . . . ? C17 C16 N5 C20 -1.3(7) . . . . ? N6 C16 N5 C20 177.1(4) . . . . ? C17 C16 N5 Cu2 170.5(4) . . . . ? N6 C16 N5 Cu2 -11.1(5) . . . . ? C19 C20 N5 C16 1.8(8) . . . . ? C19 C20 N5 Cu2 -169.5(4) . . . . ? N7 Cu2 N5 C16 41.3(4) . . . . ? Cu1 Cu2 N5 C16 -146.4(3) . . . . ? I1 Cu2 N5 C16 -81.1(3) . . . . ? I2 Cu2 N5 C16 148.2(3) . . . . ? N7 Cu2 N5 C20 -147.5(4) . . . . ? Cu1 Cu2 N5 C20 24.8(5) . . . . ? I1 Cu2 N5 C20 90.1(4) . . . . ? I2 Cu2 N5 C20 -40.6(4) . . . . ? N4 C15 N6 C21 172.6(4) . . . . ? C14 C15 N6 C21 -8.6(6) . . . . ? N4 C15 N6 C16 7.6(6) . . . . ? C14 C15 N6 C16 -173.6(4) . . . . ? N7 C21 N6 C15 -91.5(5) . . . . ? C22 C21 N6 C15 88.8(6) . . . . ? N7 C21 N6 C16 73.6(6) . . . . ? C22 C21 N6 C16 -106.1(5) . . . . ? N5 C16 N6 C15 112.1(5) . . . . ? C17 C16 N6 C15 -69.4(6) . . . . ? N5 C16 N6 C21 -53.0(6) . . . . ? C17 C16 N6 C21 125.5(5) . . . . ? C24 C25 N7 C21 -0.7(8) . . . . ? C24 C25 N7 Cu2 -158.8(5) . . . . ? C22 C21 N7 C25 -0.8(8) . . . . ? N6 C21 N7 C25 179.6(4) . . . . ? C22 C21 N7 Cu2 159.3(4) . . . . ? N6 C21 N7 Cu2 -20.4(5) . . . . ? N5 Cu2 N7 C25 134.1(4) . . . . ? Cu1 Cu2 N7 C25 -40.1(5) . . . . ? I1 Cu2 N7 C25 -113.7(4) . . . . ? I2 Cu2 N7 C25 25.3(4) . . . . ? N5 Cu2 N7 C21 -24.2(4) . . . . ? Cu1 Cu2 N7 C21 161.6(3) . . . . ? I1 Cu2 N7 C21 88.0(3) . . . . ? I2 Cu2 N7 C21 -133.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.193 _refine_diff_density_min -0.485 _refine_diff_density_rms 0.107 #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 773757' #TrackingRef '- 1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 Br3 Cu3 N3 O0' _chemical_formula_weight 638.59 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.3130(9) _cell_length_b 17.5191(12) _cell_length_c 7.3772(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.2390(10) _cell_angle_gamma 90.00 _cell_volume 1542.47(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.750 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1204 _exptl_absorpt_coefficient_mu 11.865 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2000 _exptl_absorpt_correction_T_max 0.3301 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _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 APEX area-dectector diffractometer' _diffrn_measurement_method '\f and \w-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7232 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2697 _reflns_number_gt 2173 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material SHELXL-97 _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^)+(0.0631P)^2^+2.0828P] 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 2697 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1119 _refine_ls_wR_factor_gt 0.1028 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.59145(6) 1.23244(4) 0.06617(10) 0.0450(2) Uani 1 1 d . . . Br2 Br 0.88536(5) 1.18658(4) -0.02609(9) 0.0357(2) Uani 1 1 d . . . Br3 Br 0.78398(5) 1.09013(4) -0.54977(9) 0.0371(2) Uani 1 1 d . . . C1 C 0.5778(6) 1.0462(4) -0.1753(9) 0.0398(16) Uani 1 1 d . . . H1 H 0.5575 1.0973 -0.1926 0.048 Uiso 1 1 calc R . . C2 C 0.5079(5) 0.9923(4) -0.2780(9) 0.0407(17) Uani 1 1 d . . . H2 H 0.4403 1.0064 -0.3587 0.049 Uiso 1 1 calc R . . C3 C 0.5401(6) 0.9168(4) -0.2589(9) 0.0418(17) Uani 1 1 d . . . H3 H 0.4943 0.8789 -0.3256 0.050 Uiso 1 1 calc R . . C4 C 0.6421(6) 0.8984(4) -0.1382(10) 0.0396(16) Uani 1 1 d . . . H4 H 0.6677 0.8483 -0.1278 0.048 Uiso 1 1 calc R . . C5 C 0.7046(5) 0.9554(3) -0.0344(8) 0.0262(13) Uani 1 1 d . . . C6 C 0.8114(5) 0.8923(3) 0.2469(8) 0.0272(13) Uani 1 1 d . . . C7 C 0.7132(5) 0.8690(4) 0.2935(9) 0.0363(15) Uani 1 1 d . . . H7 H 0.6442 0.8843 0.2192 0.044 Uiso 1 1 calc R . . C8 C 0.7166(6) 0.8241(4) 0.4465(9) 0.0408(16) Uani 1 1 d . . . H8 H 0.6509 0.8073 0.4742 0.049 Uiso 1 1 calc R . . C9 C 0.8213(6) 0.8039(4) 0.5605(9) 0.0409(17) Uani 1 1 d . . . H9 H 0.8275 0.7755 0.6691 0.049 Uiso 1 1 calc R . . C10 C 0.9144(6) 0.8274(4) 0.5056(9) 0.0369(15) Uani 1 1 d . . . H10 H 0.9841 0.8136 0.5800 0.044 Uiso 1 1 calc R . . C11 C 0.9073(5) 0.9693(3) 0.0512(8) 0.0270(13) Uani 1 1 d . . . C12 C 0.9170(5) 0.9649(4) -0.1333(8) 0.0302(13) Uani 1 1 d . . . H12 H 0.8605 0.9418 -0.2237 0.036 Uiso 1 1 calc R . . C13 C 0.9909(5) 1.0055(3) 0.1826(8) 0.0261(13) Uani 1 1 d . . . H13A H 0.9848 1.0098 0.3054 0.031 Uiso 1 1 calc R . . Cu1 Cu 0.75421(9) 1.11517(6) 0.11050(13) 0.0522(3) Uani 1 1 d . . . Cu2 Cu 0.72119(9) 1.27343(7) -0.12536(16) 0.0640(3) Uani 1 1 d . . . Cu3 Cu 0.93925(7) 1.12129(6) -0.27754(12) 0.0479(3) Uani 1 1 d . . . N1 N 0.6741(4) 1.0286(3) -0.0508(7) 0.0326(12) Uani 1 1 d . . . N2 N 0.8087(4) 0.9389(3) 0.0946(7) 0.0286(11) Uani 1 1 d . . . N3 N 0.9119(4) 0.8692(3) 0.3516(7) 0.0292(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0438(4) 0.0515(5) 0.0411(4) 0.0063(3) 0.0132(3) 0.0004(3) Br2 0.0354(4) 0.0331(4) 0.0408(4) 0.0013(3) 0.0133(3) 0.0020(3) Br3 0.0317(4) 0.0402(4) 0.0355(4) 0.0005(3) 0.0012(3) -0.0003(3) C1 0.038(4) 0.040(4) 0.040(4) 0.004(3) 0.006(3) 0.007(3) C2 0.021(3) 0.058(5) 0.039(4) 0.001(3) -0.002(3) 0.005(3) C3 0.029(4) 0.051(4) 0.041(4) -0.005(3) 0.002(3) -0.015(3) C4 0.040(4) 0.034(4) 0.046(4) 0.001(3) 0.013(3) 0.001(3) C5 0.016(3) 0.031(3) 0.031(3) 0.003(3) 0.005(2) -0.003(2) C6 0.023(3) 0.027(3) 0.030(3) -0.002(3) 0.004(3) -0.004(3) C7 0.021(3) 0.039(4) 0.047(4) 0.006(3) 0.006(3) 0.002(3) C8 0.044(4) 0.041(4) 0.043(4) 0.000(3) 0.021(3) -0.009(3) C9 0.056(5) 0.032(4) 0.041(4) 0.011(3) 0.022(3) 0.003(3) C10 0.037(4) 0.033(3) 0.038(4) 0.004(3) 0.005(3) 0.007(3) C11 0.024(3) 0.024(3) 0.034(3) 0.003(3) 0.009(2) 0.004(3) C12 0.025(3) 0.030(3) 0.034(3) 0.000(3) 0.004(3) 0.004(3) C13 0.024(3) 0.029(3) 0.025(3) 0.004(2) 0.005(2) 0.002(3) Cu1 0.0555(6) 0.0494(6) 0.0496(5) -0.0063(4) 0.0090(5) -0.0156(5) Cu2 0.0522(6) 0.0668(7) 0.0723(7) 0.0100(5) 0.0143(5) 0.0015(5) Cu3 0.0307(5) 0.0677(7) 0.0461(5) -0.0023(4) 0.0109(4) 0.0043(4) N1 0.028(3) 0.032(3) 0.035(3) 0.002(2) 0.003(2) 0.003(2) N2 0.015(2) 0.034(3) 0.034(3) 0.007(2) 0.001(2) -0.004(2) N3 0.029(3) 0.027(3) 0.033(3) 0.000(2) 0.011(2) 0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Cu2 2.4398(13) 4_586 ? Br1 Cu2 2.4848(13) . ? Br1 Cu1 2.8321(13) . ? Br2 Cu3 2.4074(11) . ? Br2 Cu1 2.4472(12) . ? Br2 Cu2 2.4918(13) . ? Br3 Cu3 2.4694(11) . ? Br3 Cu1 2.4812(11) 1_554 ? Br3 Cu2 2.5318(14) 4_585 ? C1 N1 1.345(8) . ? C1 C2 1.373(10) . ? C1 H1 0.9300 . ? C2 C3 1.379(11) . ? C2 H2 0.9300 . ? C3 C4 1.387(10) . ? C3 H3 0.9300 . ? C4 C5 1.374(9) . ? C4 H4 0.9300 . ? C5 N1 1.333(8) . ? C5 N2 1.425(7) . ? C6 N3 1.349(8) . ? C6 N2 1.383(7) . ? C6 C7 1.397(9) . ? C7 C8 1.368(9) . ? C7 H7 0.9300 . ? C8 C9 1.401(10) . ? C8 H8 0.9300 . ? C9 C10 1.369(9) . ? C9 H9 0.9300 . ? C10 N3 1.346(8) . ? C10 H10 0.9300 . ? C11 C13 1.382(8) . ? C11 C12 1.397(8) . ? C11 N2 1.433(7) . ? C12 C13 1.374(8) 3_775 ? C12 H12 0.9300 . ? C13 C12 1.374(8) 3_775 ? C13 Cu3 2.422(6) 3_775 ? C13 H13A 0.9300 . ? Cu1 N1 2.028(5) . ? Cu1 Br3 2.4812(11) 1_556 ? Cu1 Cu2 2.8567(15) 4_586 ? Cu2 Br1 2.4398(13) 4_585 ? Cu2 Br3 2.5318(14) 4_586 ? Cu2 Cu1 2.8567(15) 4_585 ? Cu3 N3 2.044(5) 3_775 ? Cu3 C13 2.422(6) 3_775 ? N3 Cu3 2.044(5) 3_775 ? 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 Cu2 Br1 Cu2 100.23(5) 4_586 . ? Cu2 Br1 Cu1 65.13(4) 4_586 . ? Cu2 Br1 Cu1 74.91(4) . . ? Cu3 Br2 Cu1 114.16(4) . . ? Cu3 Br2 Cu2 114.90(4) . . ? Cu1 Br2 Cu2 82.15(4) . . ? Cu3 Br3 Cu1 132.44(4) . 1_554 ? Cu3 Br3 Cu2 95.96(4) . 4_585 ? Cu1 Br3 Cu2 69.47(4) 1_554 4_585 ? N1 C1 C2 123.1(6) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C1 C2 C3 118.6(6) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C2 C3 C4 118.7(6) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 118.9(6) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N1 C5 C4 122.8(6) . . ? N1 C5 N2 116.3(5) . . ? C4 C5 N2 120.9(6) . . ? N3 C6 N2 118.5(5) . . ? N3 C6 C7 119.9(6) . . ? N2 C6 C7 121.6(5) . . ? C8 C7 C6 121.2(6) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C9 118.5(6) . . ? C7 C8 H8 120.7 . . ? C9 C8 H8 120.7 . . ? C10 C9 C8 117.4(6) . . ? C10 C9 H9 121.3 . . ? C8 C9 H9 121.3 . . ? N3 C10 C9 124.5(6) . . ? N3 C10 H10 117.8 . . ? C9 C10 H10 117.8 . . ? C13 C11 C12 118.8(6) . . ? C13 C11 N2 122.6(5) . . ? C12 C11 N2 118.5(5) . . ? C13 C12 C11 120.7(6) 3_775 . ? C13 C12 H12 119.6 3_775 . ? C11 C12 H12 119.6 . . ? C12 C13 C11 120.5(5) 3_775 . ? C12 C13 Cu3 99.5(4) 3_775 3_775 ? C11 C13 Cu3 86.1(4) . 3_775 ? C12 C13 H13A 119.7 3_775 . ? C11 C13 H13A 119.7 . . ? Cu3 C13 H13A 84.4 3_775 . ? N1 Cu1 Br2 114.57(15) . . ? N1 Cu1 Br3 112.97(15) . 1_556 ? Br2 Cu1 Br3 123.91(4) . 1_556 ? N1 Cu1 Br1 104.26(15) . . ? Br2 Cu1 Br1 95.82(4) . . ? Br3 Cu1 Br1 99.75(4) 1_556 . ? N1 Cu1 Cu2 141.34(16) . 4_586 ? Br2 Cu1 Cu2 98.67(4) . 4_586 ? Br3 Cu1 Cu2 56.10(3) 1_556 4_586 ? Br1 Cu1 Cu2 50.79(3) . 4_586 ? Br1 Cu2 Br1 98.81(5) 4_585 . ? Br1 Cu2 Br2 123.10(5) 4_585 . ? Br1 Cu2 Br2 104.18(5) . . ? Br1 Cu2 Br3 109.85(5) 4_585 4_586 ? Br1 Cu2 Br3 110.60(5) . 4_586 ? Br2 Cu2 Br3 109.27(5) . 4_586 ? Br1 Cu2 Cu1 64.08(4) 4_585 4_585 ? Br1 Cu2 Cu1 143.57(5) . 4_585 ? Br2 Cu2 Cu1 112.11(5) . 4_585 ? Br3 Cu2 Cu1 54.43(3) 4_586 4_585 ? N3 Cu3 Br2 127.05(15) 3_775 . ? N3 Cu3 C13 82.8(2) 3_775 3_775 ? Br2 Cu3 C13 111.01(14) . 3_775 ? N3 Cu3 Br3 111.50(14) 3_775 . ? Br2 Cu3 Br3 115.26(4) . . ? C13 Cu3 Br3 100.44(14) 3_775 . ? C5 N1 C1 117.7(6) . . ? C5 N1 Cu1 125.5(4) . . ? C1 N1 Cu1 116.7(4) . . ? C6 N2 C5 120.0(5) . . ? C6 N2 C11 123.3(5) . . ? C5 N2 C11 116.6(5) . . ? C10 N3 C6 118.3(5) . . ? C10 N3 Cu3 115.7(4) . 3_775 ? C6 N3 Cu3 125.4(4) . 3_775 ? 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 -2.9(11) . . . . ? C1 C2 C3 C4 -0.6(10) . . . . ? C2 C3 C4 C5 3.5(10) . . . . ? C3 C4 C5 N1 -3.3(10) . . . . ? C3 C4 C5 N2 178.5(6) . . . . ? N3 C6 C7 C8 1.3(10) . . . . ? N2 C6 C7 C8 -178.7(6) . . . . ? C6 C7 C8 C9 2.3(10) . . . . ? C7 C8 C9 C10 -3.2(10) . . . . ? C8 C9 C10 N3 0.8(11) . . . . ? C13 C11 C12 C13 1.4(10) . . . 3_775 ? N2 C11 C12 C13 178.8(5) . . . 3_775 ? C12 C11 C13 C12 -1.4(10) . . . 3_775 ? N2 C11 C13 C12 -178.7(5) . . . 3_775 ? C12 C11 C13 Cu3 -100.2(5) . . . 3_775 ? N2 C11 C13 Cu3 82.6(5) . . . 3_775 ? Cu3 Br2 Cu1 N1 -17.55(17) . . . . ? Cu2 Br2 Cu1 N1 96.28(17) . . . . ? Cu3 Br2 Cu1 Br3 127.96(5) . . . 1_556 ? Cu2 Br2 Cu1 Br3 -118.21(6) . . . 1_556 ? Cu3 Br2 Cu1 Br1 -126.15(4) . . . . ? Cu2 Br2 Cu1 Br1 -12.32(4) . . . . ? Cu3 Br2 Cu1 Cu2 -177.31(4) . . . 4_586 ? Cu2 Br2 Cu1 Cu2 -63.48(3) . . . 4_586 ? Cu2 Br1 Cu1 N1 146.35(16) 4_586 . . . ? Cu2 Br1 Cu1 N1 -104.52(16) . . . . ? Cu2 Br1 Cu1 Br2 -96.44(4) 4_586 . . . ? Cu2 Br1 Cu1 Br2 12.68(4) . . . . ? Cu2 Br1 Cu1 Br3 29.46(4) 4_586 . . 1_556 ? Cu2 Br1 Cu1 Br3 138.59(4) . . . 1_556 ? Cu2 Br1 Cu1 Cu2 109.13(4) . . . 4_586 ? Cu2 Br1 Cu2 Br1 175.32(6) 4_586 . . 4_585 ? Cu1 Br1 Cu2 Br1 114.75(5) . . . 4_585 ? Cu2 Br1 Cu2 Br2 47.79(4) 4_586 . . . ? Cu1 Br1 Cu2 Br2 -12.78(4) . . . . ? Cu2 Br1 Cu2 Br3 -69.51(5) 4_586 . . 4_586 ? Cu1 Br1 Cu2 Br3 -130.08(5) . . . 4_586 ? Cu2 Br1 Cu2 Cu1 -127.01(10) 4_586 . . 4_585 ? Cu1 Br1 Cu2 Cu1 172.42(10) . . . 4_585 ? Cu3 Br2 Cu2 Br1 16.81(7) . . . 4_585 ? Cu1 Br2 Cu2 Br1 -96.24(6) . . . 4_585 ? Cu3 Br2 Cu2 Br1 127.50(5) . . . . ? Cu1 Br2 Cu2 Br1 14.45(5) . . . . ? Cu3 Br2 Cu2 Br3 -114.29(5) . . . 4_586 ? Cu1 Br2 Cu2 Br3 132.66(5) . . . 4_586 ? Cu3 Br2 Cu2 Cu1 -55.83(6) . . . 4_585 ? Cu1 Br2 Cu2 Cu1 -168.88(5) . . . 4_585 ? Cu1 Br2 Cu3 N3 -150.05(18) . . . 3_775 ? Cu2 Br2 Cu3 N3 117.48(18) . . . 3_775 ? Cu1 Br2 Cu3 C13 -53.11(15) . . . 3_775 ? Cu2 Br2 Cu3 C13 -145.59(15) . . . 3_775 ? Cu1 Br2 Cu3 Br3 60.20(6) . . . . ? Cu2 Br2 Cu3 Br3 -32.27(7) . . . . ? Cu1 Br3 Cu3 N3 -26.91(17) 1_554 . . 3_775 ? Cu2 Br3 Cu3 N3 -94.44(16) 4_585 . . 3_775 ? Cu1 Br3 Cu3 Br2 127.49(6) 1_554 . . . ? Cu2 Br3 Cu3 Br2 59.96(5) 4_585 . . . ? Cu1 Br3 Cu3 C13 -113.18(15) 1_554 . . 3_775 ? Cu2 Br3 Cu3 C13 179.30(14) 4_585 . . 3_775 ? C4 C5 N1 C1 -0.1(9) . . . . ? N2 C5 N1 C1 178.2(5) . . . . ? C4 C5 N1 Cu1 174.8(5) . . . . ? N2 C5 N1 Cu1 -6.9(8) . . . . ? C2 C1 N1 C5 3.2(10) . . . . ? C2 C1 N1 Cu1 -172.1(5) . . . . ? Br2 Cu1 N1 C5 96.8(5) . . . . ? Br3 Cu1 N1 C5 -52.5(5) 1_556 . . . ? Br1 Cu1 N1 C5 -159.8(5) . . . . ? Cu2 Cu1 N1 C5 -116.4(5) 4_586 . . . ? Br2 Cu1 N1 C1 -88.3(5) . . . . ? Br3 Cu1 N1 C1 122.4(4) 1_556 . . . ? Br1 Cu1 N1 C1 15.1(5) . . . . ? Cu2 Cu1 N1 C1 58.5(6) 4_586 . . . ? N3 C6 N2 C5 171.0(5) . . . . ? C7 C6 N2 C5 -9.0(9) . . . . ? N3 C6 N2 C11 -5.5(9) . . . . ? C7 C6 N2 C11 174.6(6) . . . . ? N1 C5 N2 C6 118.5(6) . . . . ? C4 C5 N2 C6 -63.2(8) . . . . ? N1 C5 N2 C11 -64.9(7) . . . . ? C4 C5 N2 C11 113.4(6) . . . . ? C13 C11 N2 C6 -49.2(8) . . . . ? C12 C11 N2 C6 133.6(6) . . . . ? C13 C11 N2 C5 134.3(6) . . . . ? C12 C11 N2 C5 -43.0(8) . . . . ? C9 C10 N3 C6 2.7(10) . . . . ? C9 C10 N3 Cu3 -168.7(5) . . . 3_775 ? N2 C6 N3 C10 176.3(6) . . . . ? C7 C6 N3 C10 -3.7(9) . . . . ? N2 C6 N3 Cu3 -13.1(8) . . . 3_775 ? C7 C6 N3 Cu3 166.8(5) . . . 3_775 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.192 _refine_diff_density_min -0.868 _refine_diff_density_rms 0.151 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 773758' #TrackingRef '- 1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10 Cu N4' _chemical_formula_weight 297.80 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.1973(18) _cell_length_b 15.376(3) _cell_length_c 9.1789(18) _cell_angle_alpha 90.00 _cell_angle_beta 111.737(3) _cell_angle_gamma 90.00 _cell_volume 1205.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plane _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.641 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 1.800 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5635 _exptl_absorpt_correction_T_max 0.8694 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _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 APEX area-dectector diffractometer' _diffrn_measurement_method '\f and \w-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5200 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2119 _reflns_number_gt 1733 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material SHELXL-97 _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^)+(0.0492P)^2^+0.6176P] 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 2119 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0958 _refine_ls_wR_factor_gt 0.0884 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.23248(5) 0.19111(2) 0.40874(4) 0.04067(17) Uani 1 1 d . . . C1 C 0.5782(4) 0.2094(2) 0.5612(4) 0.0560(10) Uani 1 1 d . . . H1 H 0.5488 0.2382 0.6351 0.067 Uiso 1 1 calc R . . C2 C 0.7243(4) 0.2249(3) 0.5617(4) 0.0565(10) Uani 1 1 d . . . H2 H 0.7913 0.2642 0.6317 0.068 Uiso 1 1 calc R . . C3 C 0.7695(4) 0.1806(2) 0.4557(4) 0.0502(9) Uani 1 1 d . . . H3 H 0.8683 0.1896 0.4525 0.060 Uiso 1 1 calc R . . C4 C 0.6676(4) 0.1230(2) 0.3547(4) 0.0458(8) Uani 1 1 d . . . H4 H 0.6979 0.0916 0.2840 0.055 Uiso 1 1 calc R . . C5 C 0.5186(3) 0.11151(19) 0.3582(3) 0.0351(7) Uani 1 1 d . . . C6 C 0.2677(3) 0.02180(19) 0.2494(3) 0.0362(7) Uani 1 1 d . . . C7 C 0.2005(4) -0.0505(2) 0.1571(4) 0.0498(8) Uani 1 1 d . . . H7 H 0.2493 -0.0763 0.0957 0.060 Uiso 1 1 calc R . . C8 C 0.0620(4) -0.0831(2) 0.1575(4) 0.0590(10) Uani 1 1 d . . . H8 H 0.0155 -0.1306 0.0951 0.071 Uiso 1 1 calc R . . C9 C -0.0079(4) -0.0453(2) 0.2504(4) 0.0539(9) Uani 1 1 d . . . H9 H -0.1000 -0.0676 0.2553 0.065 Uiso 1 1 calc R . . C10 C 0.0622(4) 0.0255(2) 0.3345(4) 0.0507(9) Uani 1 1 d . . . H10 H 0.0143 0.0518 0.3963 0.061 Uiso 1 1 calc R . . C11 C 0.4563(3) 0.02578(19) 0.1219(3) 0.0358(7) Uani 1 1 d . . . C12 C 0.5446(4) -0.0490(2) 0.1373(4) 0.0396(7) Uani 1 1 d . . . H12 H 0.5746 -0.0816 0.2290 0.047 Uiso 1 1 calc R . . C13 C 0.4120(4) 0.07465(19) -0.0135(3) 0.0392(7) Uani 1 1 d . . . H13 H 0.3530 0.1249 -0.0222 0.047 Uiso 1 1 calc R . . C14 C 0.1934(3) 0.24699(18) 0.2063(3) 0.0377(6) Uani 0.50 1 d P . . C14' C 0.1995(4) 0.27213(19) 0.0909(4) 0.0472(7) Uani 0.50 1 d P . . N1 N 0.4734(3) 0.15500(18) 0.4603(3) 0.0454(7) Uani 1 1 d . . . N2 N 0.4112(3) 0.05464(16) 0.2491(3) 0.0376(6) Uani 1 1 d . . . N3 N 0.1970(3) 0.06077(17) 0.3350(3) 0.0429(6) Uani 1 1 d . . . N4 N 0.1995(4) 0.27213(19) 0.0909(4) 0.0472(7) Uani 0.50 1 d P . . N4' N 0.1934(3) 0.24699(18) 0.2063(3) 0.0377(6) Uani 0.50 1 d P . . 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 0.0497(3) 0.0447(3) 0.0359(2) -0.00266(16) 0.02552(19) 0.00100(17) C1 0.050(2) 0.064(2) 0.048(2) -0.0202(18) 0.0119(17) 0.0017(18) C2 0.050(2) 0.055(2) 0.052(2) -0.0130(18) 0.0039(17) -0.0075(18) C3 0.0387(19) 0.055(2) 0.0544(19) -0.0014(17) 0.0146(16) -0.0072(16) C4 0.0429(19) 0.052(2) 0.0473(18) -0.0058(16) 0.0220(15) -0.0007(16) C5 0.0363(17) 0.0340(15) 0.0350(15) 0.0004(13) 0.0130(13) 0.0017(13) C6 0.0375(17) 0.0364(16) 0.0368(15) -0.0004(13) 0.0161(13) 0.0002(13) C7 0.047(2) 0.0464(19) 0.060(2) -0.0142(17) 0.0253(17) -0.0057(16) C8 0.052(2) 0.054(2) 0.067(2) -0.0082(19) 0.0163(18) -0.0120(18) C9 0.042(2) 0.054(2) 0.069(2) 0.0123(19) 0.0240(18) -0.0043(17) C10 0.052(2) 0.051(2) 0.063(2) 0.0051(17) 0.0376(18) 0.0009(17) C11 0.0323(16) 0.0380(16) 0.0419(16) -0.0093(14) 0.0194(13) -0.0034(13) C12 0.0410(18) 0.0388(16) 0.0419(16) 0.0002(14) 0.0188(14) 0.0051(14) C13 0.0397(17) 0.0330(16) 0.0486(17) -0.0056(14) 0.0206(14) 0.0055(14) C14 0.0534(18) 0.0417(16) 0.0283(13) 0.0090(12) 0.0272(13) 0.0044(13) C14' 0.0489(18) 0.0425(17) 0.0527(18) -0.0078(15) 0.0220(14) 0.0008(15) N1 0.0405(16) 0.0538(16) 0.0412(14) -0.0114(13) 0.0144(12) 0.0037(13) N2 0.0376(14) 0.0391(14) 0.0429(14) -0.0109(12) 0.0227(11) -0.0037(11) N3 0.0480(16) 0.0383(14) 0.0522(15) 0.0002(13) 0.0299(13) -0.0031(12) N4 0.0489(18) 0.0425(17) 0.0527(18) -0.0078(15) 0.0220(14) 0.0008(15) N4' 0.0534(18) 0.0417(16) 0.0283(13) 0.0090(12) 0.0272(13) 0.0044(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 1.893(3) 4_566 ? Cu1 C14' 1.893(3) 4_566 ? Cu1 C14 1.955(3) . ? Cu1 N3 2.102(3) . ? Cu1 N1 2.160(3) . ? C1 N1 1.351(4) . ? C1 C2 1.363(5) . ? C1 H1 0.9300 . ? C2 C3 1.372(5) . ? C2 H2 0.9300 . ? C3 C4 1.371(5) . ? C3 H3 0.9300 . ? C4 C5 1.394(4) . ? C4 H4 0.9300 . ? C5 N1 1.337(4) . ? C5 N2 1.418(4) . ? C6 N3 1.334(4) . ? C6 C7 1.395(4) . ? C6 N2 1.414(4) . ? C7 C8 1.370(5) . ? C7 H7 0.9300 . ? C8 C9 1.372(5) . ? C8 H8 0.9300 . ? C9 C10 1.352(5) . ? C9 H9 0.9300 . ? C10 N3 1.351(4) . ? C10 H10 0.9300 . ? C11 C13 1.378(4) . ? C11 C12 1.384(4) . ? C11 N2 1.446(3) . ? C12 C13 1.394(4) 3_655 ? C12 H12 0.9300 . ? C13 C12 1.394(4) 3_655 ? C13 H13 0.9300 . ? C14 C14' 1.148(4) . ? C14' Cu1 1.893(3) 4_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Cu1 C14' 0.00(16) 4_566 4_566 ? N4 Cu1 C14 132.43(12) 4_566 . ? C14' Cu1 C14 132.43(12) 4_566 . ? N4 Cu1 N3 120.82(11) 4_566 . ? C14' Cu1 N3 120.82(11) 4_566 . ? C14 Cu1 N3 99.28(11) . . ? N4 Cu1 N1 111.72(12) 4_566 . ? C14' Cu1 N1 111.72(12) 4_566 . ? C14 Cu1 N1 97.71(11) . . ? N3 Cu1 N1 81.37(10) . . ? N1 C1 C2 124.3(3) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C1 C2 C3 117.9(3) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 119.3(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 119.9(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? N1 C5 C4 121.1(3) . . ? N1 C5 N2 119.2(3) . . ? C4 C5 N2 119.7(3) . . ? N3 C6 C7 120.8(3) . . ? N3 C6 N2 120.0(3) . . ? C7 C6 N2 119.1(3) . . ? C8 C7 C6 119.5(3) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C9 C8 C7 119.8(3) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C10 C9 C8 117.5(3) . . ? C10 C9 H9 121.3 . . ? C8 C9 H9 121.3 . . ? N3 C10 C9 124.6(3) . . ? N3 C10 H10 117.7 . . ? C9 C10 H10 117.7 . . ? C13 C11 C12 120.7(3) . . ? C13 C11 N2 118.9(3) . . ? C12 C11 N2 120.4(3) . . ? C11 C12 C13 119.1(3) . 3_655 ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 3_655 . ? C11 C13 C12 120.2(3) . 3_655 ? C11 C13 H13 119.9 . . ? C12 C13 H13 119.9 3_655 . ? C14' C14 Cu1 165.8(3) . . ? C14 C14' Cu1 173.7(3) . 4_565 ? C5 N1 C1 117.5(3) . . ? C5 N1 Cu1 122.3(2) . . ? C1 N1 Cu1 113.9(2) . . ? C6 N2 C5 128.7(2) . . ? C6 N2 C11 116.0(2) . . ? C5 N2 C11 115.2(2) . . ? C6 N3 C10 117.7(3) . . ? C6 N3 Cu1 124.5(2) . . ? C10 N3 Cu1 114.6(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -1.8(6) . . . . ? C1 C2 C3 C4 -0.1(6) . . . . ? C2 C3 C4 C5 1.5(5) . . . . ? C3 C4 C5 N1 -0.9(5) . . . . ? C3 C4 C5 N2 177.3(3) . . . . ? N3 C6 C7 C8 -1.7(5) . . . . ? N2 C6 C7 C8 179.6(3) . . . . ? C6 C7 C8 C9 -1.0(6) . . . . ? C7 C8 C9 C10 2.3(5) . . . . ? C8 C9 C10 N3 -1.0(5) . . . . ? C13 C11 C12 C13 -0.3(5) . . . 3_655 ? N2 C11 C12 C13 -179.2(3) . . . 3_655 ? C12 C11 C13 C12 0.3(5) . . . 3_655 ? N2 C11 C13 C12 179.2(3) . . . 3_655 ? N4 Cu1 C14 C14' 140.2(11) 4_566 . . . ? C14' Cu1 C14 C14' 140.2(11) 4_566 . . . ? N3 Cu1 C14 C14' -71.3(11) . . . . ? N1 Cu1 C14 C14' 11.2(11) . . . . ? Cu1 C14 C14' Cu1 -9(4) . . . 4_565 ? C4 C5 N1 C1 -0.9(5) . . . . ? N2 C5 N1 C1 -179.2(3) . . . . ? C4 C5 N1 Cu1 149.5(2) . . . . ? N2 C5 N1 Cu1 -28.7(4) . . . . ? C2 C1 N1 C5 2.4(5) . . . . ? C2 C1 N1 Cu1 -150.5(3) . . . . ? N4 Cu1 N1 C5 166.7(2) 4_566 . . . ? C14' Cu1 N1 C5 166.7(2) 4_566 . . . ? C14 Cu1 N1 C5 -51.4(3) . . . . ? N3 Cu1 N1 C5 46.9(3) . . . . ? N4 Cu1 N1 C1 -41.9(3) 4_566 . . . ? C14' Cu1 N1 C1 -41.9(3) 4_566 . . . ? C14 Cu1 N1 C1 100.0(3) . . . . ? N3 Cu1 N1 C1 -161.7(3) . . . . ? N3 C6 N2 C5 18.3(5) . . . . ? C7 C6 N2 C5 -162.9(3) . . . . ? N3 C6 N2 C11 -162.6(3) . . . . ? C7 C6 N2 C11 16.2(4) . . . . ? N1 C5 N2 C6 -14.2(5) . . . . ? C4 C5 N2 C6 167.5(3) . . . . ? N1 C5 N2 C11 166.7(3) . . . . ? C4 C5 N2 C11 -11.6(4) . . . . ? C13 C11 N2 C6 91.5(3) . . . . ? C12 C11 N2 C6 -89.6(3) . . . . ? C13 C11 N2 C5 -89.3(3) . . . . ? C12 C11 N2 C5 89.7(3) . . . . ? C7 C6 N3 C10 2.9(5) . . . . ? N2 C6 N3 C10 -178.3(3) . . . . ? C7 C6 N3 Cu1 -155.8(3) . . . . ? N2 C6 N3 Cu1 22.9(4) . . . . ? C9 C10 N3 C6 -1.6(5) . . . . ? C9 C10 N3 Cu1 159.2(3) . . . . ? N4 Cu1 N3 C6 -154.2(2) 4_566 . . . ? C14' Cu1 N3 C6 -154.2(2) 4_566 . . . ? C14 Cu1 N3 C6 52.5(3) . . . . ? N1 Cu1 N3 C6 -44.0(3) . . . . ? N4 Cu1 N3 C10 46.5(3) 4_566 . . . ? C14' Cu1 N3 C10 46.5(3) 4_566 . . . ? C14 Cu1 N3 C10 -106.8(2) . . . . ? N1 Cu1 N3 C10 156.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.535 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.064 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 773759' #TrackingRef '- 1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 Br Cu N6' _chemical_formula_weight 636.02 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.6291(13) _cell_length_b 11.2293(10) _cell_length_c 17.3085(15) _cell_angle_alpha 90.00 _cell_angle_beta 107.402(2) _cell_angle_gamma 90.00 _cell_volume 2713.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 2.312 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6424 _exptl_absorpt_correction_T_max 0.7231 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _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 APEX area-dectector diffractometer' _diffrn_measurement_method '\f and \w-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11767 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4771 _reflns_number_gt 3463 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material SHELXL-97 _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^)+(0.0617P)^2^+1.1766P] 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 4771 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1232 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.25473(3) -0.36619(4) -0.15911(3) 0.04028(17) Uani 1 1 d . . . Br1 Br 0.26359(3) -0.58470(4) -0.15878(3) 0.04958(17) Uani 1 1 d . . . C1 C 0.0894(3) -0.3914(4) -0.1079(2) 0.0424(10) Uani 1 1 d . . . H1 H 0.0872 -0.4617 -0.1368 0.051 Uiso 1 1 calc R . . C2 C 0.0149(3) -0.3672(5) -0.0776(3) 0.0587(13) Uani 1 1 d . . . H2 H -0.0367 -0.4190 -0.0861 0.070 Uiso 1 1 calc R . . C3 C 0.0190(3) -0.2640(5) -0.0344(3) 0.0627(14) Uani 1 1 d . . . H3 H -0.0304 -0.2447 -0.0131 0.075 Uiso 1 1 calc R . . C4 C 0.0959(3) -0.1894(4) -0.0227(3) 0.0497(11) Uani 1 1 d . . . H4 H 0.0988 -0.1188 0.0060 0.060 Uiso 1 1 calc R . . C5 C 0.1697(3) -0.2199(3) -0.0541(2) 0.0340(9) Uani 1 1 d . . . C6 C 0.3435(3) -0.1939(4) -0.0328(2) 0.0362(9) Uani 1 1 d . . . C7 C 0.4074(3) -0.1221(4) -0.0549(3) 0.0647(14) Uani 1 1 d . . . H7 H 0.3896 -0.0479 -0.0784 0.078 Uiso 1 1 calc R . . C8 C 0.4999(4) -0.1658(6) -0.0405(4) 0.089(2) Uani 1 1 d . . . H8 H 0.5462 -0.1200 -0.0535 0.107 Uiso 1 1 calc R . . C9 C 0.5227(4) -0.2772(7) -0.0068(4) 0.090(2) Uani 1 1 d . . . H9 H 0.5842 -0.3081 0.0034 0.108 Uiso 1 1 calc R . . C10 C 0.4536(4) -0.3396(5) 0.0109(3) 0.0720(16) Uani 1 1 d . . . H10 H 0.4692 -0.4148 0.0334 0.086 Uiso 1 1 calc R . . C11 C 0.2490(3) -0.0326(3) -0.0050(2) 0.0335(9) Uani 1 1 d . . . C12 C 0.2061(3) 0.0629(4) -0.0518(2) 0.0390(10) Uani 1 1 d . . . H12 H 0.1783 0.0533 -0.1072 0.047 Uiso 1 1 calc R . . C13 C 0.2041(3) 0.1739(3) -0.0164(2) 0.0373(9) Uani 1 1 d . . . H13 H 0.1756 0.2380 -0.0487 0.045 Uiso 1 1 calc R . . C14 C 0.2441(3) 0.1903(3) 0.0667(2) 0.0314(9) Uani 1 1 d . . . C15 C 0.2870(3) 0.0926(3) 0.1125(2) 0.0386(9) Uani 1 1 d . . . H15 H 0.3140 0.1013 0.1681 0.046 Uiso 1 1 calc R . . C16 C 0.2904(3) -0.0172(3) 0.0774(2) 0.0391(9) Uani 1 1 d . . . H16 H 0.3206 -0.0809 0.1092 0.047 Uiso 1 1 calc R . . C17 C 0.2420(2) 0.3084(3) 0.1045(2) 0.0311(8) Uani 1 1 d . . . C18 C 0.2471(3) 0.3181(3) 0.1863(2) 0.0373(9) Uani 1 1 d . . . H18 H 0.2482 0.2492 0.2164 0.045 Uiso 1 1 calc R . . C19 C 0.2503(3) 0.4279(3) 0.2232(2) 0.0374(9) Uani 1 1 d . . . H19 H 0.2560 0.4320 0.2781 0.045 Uiso 1 1 calc R . . C20 C 0.2453(3) 0.5306(3) 0.1795(2) 0.0328(9) Uani 1 1 d . . . C21 C 0.2366(3) 0.5231(4) 0.0977(2) 0.0419(10) Uani 1 1 d . . . H21 H 0.2311 0.5923 0.0671 0.050 Uiso 1 1 calc R . . C22 C 0.2359(3) 0.4137(3) 0.0611(2) 0.0391(9) Uani 1 1 d . . . H22 H 0.2313 0.4104 0.0064 0.047 Uiso 1 1 calc R . . C23 C 0.3353(3) 0.7109(3) 0.2349(2) 0.0341(9) Uani 1 1 d . . . C24 C 0.4113(3) 0.6735(4) 0.2074(3) 0.0453(10) Uani 1 1 d . . . H24 H 0.4058 0.6041 0.1770 0.054 Uiso 1 1 calc R . . C25 C 0.4934(3) 0.7391(4) 0.2254(3) 0.0538(12) Uani 1 1 d . . . H25 H 0.5445 0.7144 0.2078 0.065 Uiso 1 1 calc R . . C26 C 0.5001(3) 0.8423(4) 0.2699(3) 0.0559(13) Uani 1 1 d . . . H26 H 0.5549 0.8894 0.2820 0.067 Uiso 1 1 calc R . . C27 C 0.4243(3) 0.8730(4) 0.2953(3) 0.0460(10) Uani 1 1 d . . . H27 H 0.4287 0.9429 0.3250 0.055 Uiso 1 1 calc R . . C28 C 0.1606(3) 0.6962(3) 0.2169(2) 0.0359(9) Uani 1 1 d . . . C29 C 0.1017(2) 0.6256(3) 0.2398(2) 0.0325(9) Uani 1 1 d . . . H29 H 0.1201 0.5488 0.2581 0.039 Uiso 1 1 calc R . . C30 C 0.0162(3) 0.6666(5) 0.2361(3) 0.0602(13) Uani 1 1 d . . . H30 H -0.0255 0.6161 0.2517 0.072 Uiso 1 1 calc R . . C31 C -0.0149(3) 0.7781(5) 0.2110(3) 0.0583(13) Uani 1 1 d . . . H31 H -0.0753 0.8039 0.2109 0.070 Uiso 1 1 calc R . . C32 C 0.0452(3) 0.8514(4) 0.1858(3) 0.0578(13) Uani 1 1 d . . . H32 H 0.0249 0.9273 0.1667 0.069 Uiso 1 1 calc R . . N1 N 0.1656(2) -0.3192(3) -0.09820(18) 0.0326(7) Uani 1 1 d . . . N2 N 0.2504(2) -0.1477(3) -0.04093(18) 0.0341(7) Uani 1 1 d . . . N3 N 0.3640(3) -0.3017(3) -0.0015(2) 0.0516(9) Uani 1 1 d . . . N4 N 0.2503(2) 0.6462(3) 0.21728(19) 0.0374(8) Uani 1 1 d . . . N5 N 0.3432(2) 0.8093(3) 0.28064(18) 0.0343(7) Uani 1 1 d . . . N6 N 0.1375(3) 0.8125(4) 0.1887(2) 0.0677(12) 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 0.0499(3) 0.0321(3) 0.0454(3) -0.0017(2) 0.0242(2) -0.0004(2) Br1 0.0771(3) 0.0260(3) 0.0556(3) -0.00485(19) 0.0351(2) -0.0021(2) C1 0.044(2) 0.041(3) 0.042(2) -0.0040(19) 0.0117(19) -0.009(2) C2 0.041(3) 0.063(3) 0.076(3) -0.012(3) 0.023(2) -0.017(2) C3 0.044(3) 0.077(4) 0.080(4) -0.022(3) 0.037(3) -0.011(3) C4 0.041(3) 0.052(3) 0.060(3) -0.018(2) 0.022(2) 0.000(2) C5 0.034(2) 0.034(2) 0.034(2) -0.0006(18) 0.0108(17) 0.0020(18) C6 0.034(2) 0.034(2) 0.042(2) -0.0143(18) 0.0146(18) -0.0033(18) C7 0.059(3) 0.047(3) 0.104(4) -0.022(3) 0.048(3) -0.017(2) C8 0.059(4) 0.087(5) 0.139(6) -0.052(4) 0.055(4) -0.033(3) C9 0.044(3) 0.115(6) 0.109(5) -0.046(4) 0.018(3) 0.013(4) C10 0.065(4) 0.080(4) 0.065(3) -0.002(3) 0.011(3) 0.035(3) C11 0.036(2) 0.028(2) 0.039(2) -0.0052(18) 0.0149(17) 0.0009(17) C12 0.045(2) 0.039(2) 0.034(2) -0.0052(18) 0.0130(18) 0.0039(19) C13 0.050(2) 0.030(2) 0.034(2) 0.0019(17) 0.0155(19) 0.0074(19) C14 0.037(2) 0.024(2) 0.037(2) -0.0018(16) 0.0162(17) -0.0008(16) C15 0.049(2) 0.030(2) 0.035(2) -0.0009(18) 0.0103(19) 0.0002(19) C16 0.046(2) 0.027(2) 0.044(2) 0.0008(18) 0.0124(19) 0.0049(18) C17 0.032(2) 0.024(2) 0.040(2) -0.0006(16) 0.0141(17) 0.0012(16) C18 0.050(2) 0.026(2) 0.041(2) 0.0004(17) 0.0211(19) -0.0007(18) C19 0.050(2) 0.033(2) 0.035(2) -0.0034(18) 0.0208(19) 0.0002(19) C20 0.035(2) 0.025(2) 0.041(2) -0.0072(17) 0.0135(17) -0.0033(17) C21 0.057(3) 0.025(2) 0.045(2) 0.0036(18) 0.017(2) 0.0025(19) C22 0.053(3) 0.032(2) 0.034(2) -0.0020(18) 0.0160(19) 0.0018(19) C23 0.036(2) 0.030(2) 0.037(2) -0.0012(17) 0.0133(17) 0.0014(18) C24 0.045(3) 0.037(2) 0.058(3) -0.011(2) 0.021(2) 0.000(2) C25 0.039(3) 0.061(3) 0.067(3) -0.006(2) 0.024(2) 0.004(2) C26 0.040(3) 0.053(3) 0.078(3) -0.015(3) 0.023(2) -0.013(2) C27 0.044(3) 0.039(2) 0.057(3) -0.011(2) 0.018(2) -0.007(2) C28 0.042(2) 0.029(2) 0.036(2) -0.0112(17) 0.0095(18) 0.0050(18) C29 0.028(2) 0.0188(19) 0.056(3) -0.0045(17) 0.0213(18) -0.0039(16) C30 0.054(3) 0.055(3) 0.076(4) -0.013(3) 0.028(3) -0.014(3) C31 0.037(3) 0.072(4) 0.064(3) -0.013(3) 0.011(2) 0.004(3) C32 0.054(3) 0.053(3) 0.057(3) 0.000(2) 0.002(2) 0.024(3) N1 0.0367(18) 0.0285(18) 0.0344(18) -0.0024(14) 0.0135(14) -0.0018(14) N2 0.0339(18) 0.0255(18) 0.045(2) -0.0091(14) 0.0152(15) -0.0029(14) N3 0.053(2) 0.047(2) 0.053(2) 0.0053(18) 0.0147(18) 0.0151(19) N4 0.0362(18) 0.0270(18) 0.053(2) -0.0123(15) 0.0188(16) -0.0030(15) N5 0.0363(18) 0.0296(18) 0.0392(18) -0.0041(14) 0.0146(14) -0.0036(14) N6 0.076(3) 0.068(3) 0.055(3) -0.007(2) 0.012(2) 0.010(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 N1 1.978(3) . ? Cu1 N5 1.994(3) 4_565 ? Cu1 Br1 2.4571(7) . ? C1 N1 1.348(5) . ? C1 C2 1.370(6) . ? C1 H1 0.9300 . ? C2 C3 1.370(6) . ? C2 H2 0.9300 . ? C3 C4 1.368(6) . ? C3 H3 0.9300 . ? C4 C5 1.389(5) . ? C4 H4 0.9300 . ? C5 N1 1.342(5) . ? C5 N2 1.393(5) . ? C6 N3 1.324(5) . ? C6 C7 1.372(6) . ? C6 N2 1.425(5) . ? C7 C8 1.390(7) . ? C7 H7 0.9300 . ? C8 C9 1.379(9) . ? C8 H8 0.9300 . ? C9 C10 1.338(8) . ? C9 H9 0.9300 . ? C10 N3 1.333(6) . ? C10 H10 0.9300 . ? C11 C12 1.376(5) . ? C11 C16 1.384(5) . ? C11 N2 1.437(5) . ? C12 C13 1.393(5) . ? C12 H12 0.9300 . ? C13 C14 1.393(5) . ? C13 H13 0.9300 . ? C14 C15 1.388(5) . ? C14 C17 1.484(5) . ? C15 C16 1.382(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C22 1.389(5) . ? C17 C18 1.399(5) . ? C18 C19 1.384(5) . ? C18 H18 0.9300 . ? C19 C20 1.369(5) . ? C19 H19 0.9300 . ? C20 C21 1.386(5) . ? C20 N4 1.445(5) . ? C21 C22 1.381(5) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 N5 1.344(5) . ? C23 N4 1.392(5) . ? C23 C24 1.398(5) . ? C24 C25 1.364(6) . ? C24 H24 0.9300 . ? C25 C26 1.378(6) . ? C25 H25 0.9300 . ? C26 C27 1.355(5) . ? C26 H26 0.9300 . ? C27 N5 1.343(5) . ? C27 H27 0.9300 . ? C28 C29 1.316(5) . ? C28 N6 1.400(6) . ? C28 N4 1.426(5) . ? C29 C30 1.317(6) . ? C29 H29 0.9300 . ? C30 C31 1.359(7) . ? C30 H30 0.9300 . ? C31 C32 1.367(6) . ? C31 H31 0.9300 . ? C32 N6 1.406(6) . ? C32 H32 0.9300 . ? N5 Cu1 1.994(3) 4_566 ? 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 Cu1 N5 145.84(13) . 4_565 ? N1 Cu1 Br1 107.93(9) . . ? N5 Cu1 Br1 106.21(9) 4_565 . ? N1 C1 C2 123.8(4) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C3 C2 C1 117.8(4) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C4 C3 C2 119.9(4) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 119.5(4) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 121.3(4) . . ? N1 C5 N2 117.9(3) . . ? C4 C5 N2 120.8(3) . . ? N3 C6 C7 124.2(4) . . ? N3 C6 N2 117.7(3) . . ? C7 C6 N2 118.0(4) . . ? C6 C7 C8 116.8(5) . . ? C6 C7 H7 121.6 . . ? C8 C7 H7 121.6 . . ? C9 C8 C7 119.7(5) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C10 C9 C8 117.9(5) . . ? C10 C9 H9 121.1 . . ? C8 C9 H9 121.1 . . ? N3 C10 C9 124.8(6) . . ? N3 C10 H10 117.6 . . ? C9 C10 H10 117.6 . . ? C12 C11 C16 119.4(4) . . ? C12 C11 N2 120.6(3) . . ? C16 C11 N2 119.9(3) . . ? C11 C12 C13 120.3(4) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 121.0(4) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 117.6(3) . . ? C15 C14 C17 121.3(3) . . ? C13 C14 C17 121.1(3) . . ? C16 C15 C14 121.6(4) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C15 C16 C11 120.1(4) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C22 C17 C18 117.2(3) . . ? C22 C17 C14 121.9(3) . . ? C18 C17 C14 120.9(3) . . ? C19 C18 C17 121.4(4) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C20 C19 C18 120.5(4) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C21 119.1(3) . . ? C19 C20 N4 121.3(3) . . ? C21 C20 N4 119.6(3) . . ? C22 C21 C20 120.6(4) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C17 121.2(4) . . ? C21 C22 H22 119.4 . . ? C17 C22 H22 119.4 . . ? N5 C23 N4 118.1(3) . . ? N5 C23 C24 120.7(3) . . ? N4 C23 C24 121.2(3) . . ? C25 C24 C23 119.7(4) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C26 119.5(4) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C27 C26 C25 117.8(4) . . ? C27 C26 H26 121.1 . . ? C25 C26 H26 121.1 . . ? N5 C27 C26 124.5(4) . . ? N5 C27 H27 117.8 . . ? C26 C27 H27 117.8 . . ? C29 C28 N6 123.8(4) . . ? C29 C28 N4 116.5(3) . . ? N6 C28 N4 119.7(4) . . ? C28 C29 C30 118.2(4) . . ? C28 C29 H29 120.9 . . ? C30 C29 H29 120.9 . . ? C29 C30 C31 124.0(4) . . ? C29 C30 H30 118.0 . . ? C31 C30 H30 118.0 . . ? C30 C31 C32 118.1(4) . . ? C30 C31 H31 120.9 . . ? C32 C31 H31 120.9 . . ? C31 C32 N6 120.3(4) . . ? C31 C32 H32 119.9 . . ? N6 C32 H32 119.9 . . ? C5 N1 C1 117.7(3) . . ? C5 N1 Cu1 126.9(2) . . ? C1 N1 Cu1 115.2(3) . . ? C5 N2 C6 122.9(3) . . ? C5 N2 C11 118.3(3) . . ? C6 N2 C11 114.9(3) . . ? C6 N3 C10 116.7(4) . . ? C23 N4 C28 123.7(3) . . ? C23 N4 C20 119.3(3) . . ? C28 N4 C20 115.4(3) . . ? C27 N5 C23 117.7(3) . . ? C27 N5 Cu1 113.9(3) . 4_566 ? C23 N5 Cu1 128.1(2) . 4_566 ? C28 N6 C32 115.6(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.6(7) . . . . ? C1 C2 C3 C4 -0.1(8) . . . . ? C2 C3 C4 C5 -0.7(8) . . . . ? C3 C4 C5 N1 2.3(7) . . . . ? C3 C4 C5 N2 -177.8(4) . . . . ? N3 C6 C7 C8 -2.1(7) . . . . ? N2 C6 C7 C8 175.1(4) . . . . ? C6 C7 C8 C9 1.1(8) . . . . ? C7 C8 C9 C10 0.0(9) . . . . ? C8 C9 C10 N3 -0.2(9) . . . . ? C16 C11 C12 C13 -0.2(6) . . . . ? N2 C11 C12 C13 179.2(3) . . . . ? C11 C12 C13 C14 -0.9(6) . . . . ? C12 C13 C14 C15 0.9(5) . . . . ? C12 C13 C14 C17 180.0(3) . . . . ? C13 C14 C15 C16 0.2(6) . . . . ? C17 C14 C15 C16 -179.0(3) . . . . ? C14 C15 C16 C11 -1.2(6) . . . . ? C12 C11 C16 C15 1.2(6) . . . . ? N2 C11 C16 C15 -178.2(3) . . . . ? C15 C14 C17 C22 153.9(4) . . . . ? C13 C14 C17 C22 -25.2(6) . . . . ? C15 C14 C17 C18 -25.6(5) . . . . ? C13 C14 C17 C18 155.4(4) . . . . ? C22 C17 C18 C19 -3.0(6) . . . . ? C14 C17 C18 C19 176.5(4) . . . . ? C17 C18 C19 C20 2.3(6) . . . . ? C18 C19 C20 C21 0.2(6) . . . . ? C18 C19 C20 N4 -178.9(3) . . . . ? C19 C20 C21 C22 -2.0(6) . . . . ? N4 C20 C21 C22 177.1(3) . . . . ? C20 C21 C22 C17 1.3(6) . . . . ? C18 C17 C22 C21 1.2(6) . . . . ? C14 C17 C22 C21 -178.3(3) . . . . ? N5 C23 C24 C25 -1.8(6) . . . . ? N4 C23 C24 C25 179.7(4) . . . . ? C23 C24 C25 C26 -0.6(7) . . . . ? C24 C25 C26 C27 1.3(7) . . . . ? C25 C26 C27 N5 0.4(7) . . . . ? N6 C28 C29 C30 -0.1(6) . . . . ? N4 C28 C29 C30 -176.4(4) . . . . ? C28 C29 C30 C31 -0.8(7) . . . . ? C29 C30 C31 C32 1.9(8) . . . . ? C30 C31 C32 N6 -2.0(7) . . . . ? C4 C5 N1 C1 -3.0(6) . . . . ? N2 C5 N1 C1 177.2(3) . . . . ? C4 C5 N1 Cu1 171.5(3) . . . . ? N2 C5 N1 Cu1 -8.3(5) . . . . ? C2 C1 N1 C5 2.2(6) . . . . ? C2 C1 N1 Cu1 -173.0(4) . . . . ? N5 Cu1 N1 C5 -29.4(4) 4_565 . . . ? Br1 Cu1 N1 C5 148.7(3) . . . . ? N5 Cu1 N1 C1 145.2(3) 4_565 . . . ? Br1 Cu1 N1 C1 -36.7(3) . . . . ? N1 C5 N2 C6 -33.1(5) . . . . ? C4 C5 N2 C6 147.1(4) . . . . ? N1 C5 N2 C11 170.4(3) . . . . ? C4 C5 N2 C11 -9.5(5) . . . . ? N3 C6 N2 C5 -30.5(5) . . . . ? C7 C6 N2 C5 152.1(4) . . . . ? N3 C6 N2 C11 126.7(4) . . . . ? C7 C6 N2 C11 -50.7(5) . . . . ? C12 C11 N2 C5 -82.4(5) . . . . ? C16 C11 N2 C5 97.0(4) . . . . ? C12 C11 N2 C6 119.2(4) . . . . ? C16 C11 N2 C6 -61.3(5) . . . . ? C7 C6 N3 C10 1.9(6) . . . . ? N2 C6 N3 C10 -175.4(4) . . . . ? C9 C10 N3 C6 -0.6(8) . . . . ? N5 C23 N4 C28 24.7(5) . . . . ? C24 C23 N4 C28 -156.8(4) . . . . ? N5 C23 N4 C20 -170.2(3) . . . . ? C24 C23 N4 C20 8.3(6) . . . . ? C29 C28 N4 C23 -146.8(4) . . . . ? N6 C28 N4 C23 36.7(5) . . . . ? C29 C28 N4 C20 47.6(5) . . . . ? N6 C28 N4 C20 -128.9(4) . . . . ? C19 C20 N4 C23 103.0(4) . . . . ? C21 C20 N4 C23 -76.1(5) . . . . ? C19 C20 N4 C28 -90.7(4) . . . . ? C21 C20 N4 C28 90.3(4) . . . . ? C26 C27 N5 C23 -2.7(6) . . . . ? C26 C27 N5 Cu1 171.1(4) . . . 4_566 ? N4 C23 N5 C27 -178.1(3) . . . . ? C24 C23 N5 C27 3.3(6) . . . . ? N4 C23 N5 Cu1 9.1(5) . . . 4_566 ? C24 C23 N5 Cu1 -169.5(3) . . . 4_566 ? C29 C28 N6 C32 -0.1(6) . . . . ? N4 C28 N6 C32 176.1(3) . . . . ? C31 C32 N6 C28 1.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.634 _refine_diff_density_min -0.507 _refine_diff_density_rms 0.079 #===END data_6 _database_code_depnum_ccdc_archive 'CCDC 773760' #TrackingRef '- 1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 Cu2 N5.50' _chemical_formula_weight 432.41 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.7525(18) _cell_length_b 18.711(3) _cell_length_c 14.771(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3524.5(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plane _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1732 _exptl_absorpt_coefficient_mu 2.425 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.4928 _exptl_absorpt_correction_T_max 0.7596 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _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 APEX area-dectector diffractometer' _diffrn_measurement_method '\f and \w-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16824 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3113 _reflns_number_gt 2250 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material SHELXL-97 _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^)+(0.0754P)^2^+3.3041P] 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 3113 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1426 _refine_ls_wR_factor_gt 0.1263 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.82818(5) 0.41119(3) 0.14832(4) 0.0546(2) Uani 1 1 d . . . Cu2 Cu 0.81415(5) 0.15200(3) 0.16843(5) 0.0584(2) Uani 1 1 d . . . C1 C 1.0463(4) 0.3810(3) 0.0883(3) 0.0613(13) Uani 1 1 d . . . H1 H 1.0137 0.3389 0.0704 0.074 Uiso 1 1 calc R . . C2 C 1.1409(4) 0.3979(3) 0.0507(4) 0.0697(15) Uani 1 1 d . . . H2 H 1.1726 0.3676 0.0089 0.084 Uiso 1 1 calc R . . C3 C 1.1882(4) 0.4610(3) 0.0761(3) 0.0710(15) Uani 1 1 d . . . H3 H 1.2500 0.4756 0.0482 0.085 Uiso 1 1 calc R . . C4 C 1.1439(4) 0.5019(3) 0.1423(3) 0.0578(12) Uani 1 1 d . . . H4 H 1.1769 0.5432 0.1624 0.069 Uiso 1 1 calc R . . C5 C 1.0488(3) 0.4808(2) 0.1790(3) 0.0445(10) Uani 1 1 d . . . C6 C 1.0000 0.5956(3) 0.2500 0.0500(16) Uani 1 2 d S . . C7 C 1.0014(5) 0.6336(2) 0.3304(3) 0.0643(14) Uani 1 1 d . . . H7 H 1.0039 0.6092 0.3852 0.077 Uiso 1 1 calc R . . C8 C 0.9991(5) 0.7074(2) 0.3300(3) 0.0673(15) Uani 1 1 d . . . H8 H 0.9970 0.7318 0.3849 0.081 Uiso 1 1 calc R . . C9 C 1.0000 0.7458(3) 0.2500 0.0572(17) Uani 1 2 d S . . C10 C 1.0000 0.8253(3) 0.2500 0.0543(17) Uani 1 2 d S . . C11 C 0.9201(4) 0.8632(2) 0.2905(4) 0.0595(13) Uani 1 1 d . . . H11 H 0.8661 0.8388 0.3193 0.071 Uiso 1 1 calc R . . C12 C 0.9193(4) 0.9375(2) 0.2889(3) 0.0540(12) Uani 1 1 d . . . H12 H 0.8633 0.9620 0.3146 0.065 Uiso 1 1 calc R . . C13 C 1.0000 0.9751(3) 0.2500 0.0416(14) Uani 1 2 d S . . C14 C 1.0451(4) 1.0899(2) 0.1774(3) 0.0445(10) Uani 1 1 d . . . C15 C 1.0236(4) 1.0731(3) 0.0876(3) 0.0593(13) Uani 1 1 d . . . H15 H 0.9787 1.0357 0.0731 0.071 Uiso 1 1 calc R . . C16 C 1.0705(5) 1.1132(3) 0.0207(4) 0.0750(16) Uani 1 1 d . . . H16 H 1.0595 1.1021 -0.0399 0.090 Uiso 1 1 calc R . . C17 C 1.1334(5) 1.1694(3) 0.0443(4) 0.0785(16) Uani 1 1 d . . . H17 H 1.1648 1.1977 0.0002 0.094 Uiso 1 1 calc R . . C18 C 1.1490(5) 1.1828(3) 0.1343(4) 0.0700(15) Uani 1 1 d . . . H18 H 1.1905 1.2218 0.1499 0.084 Uiso 1 1 calc R . . C19 C 0.8145(4) 0.3130(2) 0.1433(4) 0.0632(14) Uani 0.50 1 d P . . C19' C 0.8128(4) 0.2515(3) 0.1462(3) 0.1273(17) Uani 0.50 1 d P . . C20 C 0.7671(4) 0.5018(2) 0.1453(3) 0.0538(10) Uani 0.50 1 d P . . C20' C 0.7325(4) 0.5585(2) 0.1482(3) 0.0497(10) Uani 0.50 1 d P . . N1 N 0.9977(3) 0.42271(18) 0.1504(3) 0.0489(9) Uani 1 1 d . . . N2 N 1.0000 0.5195(2) 0.2500 0.0454(12) Uani 1 2 d S . . N3 N 1.0000 1.0513(2) 0.2500 0.0432(12) Uani 1 2 d S . . N4 N 1.1082(3) 1.14352(17) 0.2014(3) 0.0512(9) Uani 1 1 d . . . N5 N 0.8128(4) 0.2515(3) 0.1462(3) 0.1273(17) Uani 1 1 d . . . N5' N 0.8145(4) 0.3130(2) 0.1433(4) 0.0632(14) Uani 0.50 1 d P . . N6 N 0.7325(4) 0.5585(2) 0.1482(3) 0.0497(10) Uani 0.50 1 d P . . N6' N 0.7671(4) 0.5018(2) 0.1453(3) 0.0538(10) Uani 0.50 1 d P . . 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 0.0683(4) 0.0297(3) 0.0659(4) 0.0023(2) -0.0007(3) 0.0039(2) Cu2 0.0696(4) 0.0289(3) 0.0766(5) 0.0041(3) -0.0108(3) -0.0031(2) C1 0.067(3) 0.053(3) 0.063(3) -0.011(3) 0.003(3) 0.005(2) C2 0.062(3) 0.090(4) 0.056(3) -0.015(3) 0.009(3) 0.009(3) C3 0.057(3) 0.107(5) 0.048(3) -0.001(3) 0.003(2) -0.012(3) C4 0.059(3) 0.065(3) 0.050(3) 0.003(2) -0.004(2) -0.012(2) C5 0.051(3) 0.037(2) 0.046(2) 0.0039(19) -0.003(2) 0.0000(19) C6 0.061(4) 0.028(3) 0.061(4) 0.000 -0.016(3) 0.000 C7 0.109(4) 0.035(2) 0.049(3) 0.001(2) -0.018(3) 0.009(3) C8 0.111(4) 0.037(3) 0.055(3) -0.008(2) -0.016(3) 0.006(3) C9 0.070(4) 0.032(3) 0.070(5) 0.000 -0.021(4) 0.000 C10 0.063(4) 0.028(3) 0.071(5) 0.000 -0.018(4) 0.000 C11 0.063(3) 0.040(2) 0.076(4) 0.007(2) -0.004(3) -0.009(2) C12 0.057(3) 0.035(2) 0.070(3) 0.003(2) 0.003(2) 0.002(2) C13 0.051(4) 0.028(3) 0.046(3) 0.000 -0.009(3) 0.000 C14 0.055(3) 0.032(2) 0.046(3) 0.0001(19) 0.001(2) 0.0028(19) C15 0.075(3) 0.054(3) 0.049(3) -0.006(2) -0.001(2) -0.005(2) C16 0.106(5) 0.073(4) 0.046(3) 0.000(3) 0.007(3) 0.006(3) C17 0.103(5) 0.064(3) 0.068(4) 0.017(3) 0.017(3) -0.013(3) C18 0.086(4) 0.049(3) 0.075(4) 0.012(3) -0.005(3) -0.021(3) C19 0.076(3) 0.0110(17) 0.103(4) 0.006(2) -0.018(3) -0.0033(18) C19' 0.107(4) 0.143(4) 0.132(4) 0.005(4) -0.027(3) -0.005(3) C20 0.061(3) 0.043(2) 0.057(3) 0.005(2) 0.004(2) -0.004(2) C20' 0.067(3) 0.0264(19) 0.056(3) 0.0035(18) 0.010(2) 0.0081(19) N1 0.055(2) 0.0386(19) 0.053(2) -0.0040(17) 0.0011(18) 0.0026(17) N2 0.057(3) 0.027(2) 0.052(3) 0.000 0.001(2) 0.000 N3 0.055(3) 0.029(2) 0.046(3) 0.000 0.001(2) 0.000 N4 0.065(2) 0.0354(19) 0.053(2) 0.0055(17) -0.0041(19) -0.0061(17) N5 0.107(4) 0.143(4) 0.132(4) 0.005(4) -0.027(3) -0.005(3) N5' 0.076(3) 0.0110(17) 0.103(4) 0.006(2) -0.018(3) -0.0033(18) N6 0.067(3) 0.0264(19) 0.056(3) 0.0035(18) 0.010(2) 0.0081(19) N6' 0.061(3) 0.043(2) 0.057(3) 0.005(2) 0.004(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 C19 1.846(4) . ? Cu1 C20 1.867(4) . ? Cu1 N1 2.173(4) . ? Cu2 N6 1.872(4) 8_755 ? Cu2 C20' 1.872(4) 8_755 ? Cu2 C19' 1.891(6) . ? Cu2 N4 2.168(4) 3_745 ? C1 N1 1.354(6) . ? C1 C2 1.365(7) . ? C1 H1 0.9300 . ? C2 C3 1.377(7) . ? C2 H2 0.9300 . ? C3 C4 1.365(7) . ? C3 H3 0.9300 . ? C4 C5 1.386(6) . ? C4 H4 0.9300 . ? C5 N1 1.336(5) . ? C5 N2 1.418(5) . ? C6 C7 1.384(5) . ? C6 C7 1.384(5) 3_755 ? C6 N2 1.424(7) . ? C7 C8 1.381(6) . ? C7 H7 0.9300 . ? C8 C9 1.384(6) . ? C8 H8 0.9300 . ? C9 C8 1.384(6) 3_755 ? C9 C10 1.486(8) . ? C10 C11 1.378(6) 3_755 ? C10 C11 1.378(6) . ? C11 C12 1.390(6) . ? C11 H11 0.9300 . ? C12 C13 1.373(5) . ? C12 H12 0.9300 . ? C13 C12 1.373(5) 3_755 ? C13 N3 1.425(6) . ? C14 N4 1.335(5) . ? C14 C15 1.389(6) . ? C14 N3 1.416(5) . ? C15 C16 1.378(7) . ? C15 H15 0.9300 . ? C16 C17 1.368(7) . ? C16 H16 0.9300 . ? C17 C18 1.368(8) . ? C17 H17 0.9300 . ? C18 N4 1.340(6) . ? C18 H18 0.9300 . ? C19 C19' 1.152(7) . ? C20 C20' 1.149(6) . ? C20' Cu2 1.872(4) 8_765 ? N2 C5 1.418(5) 3_755 ? N3 C14 1.416(5) 3_755 ? N4 Cu2 2.168(4) 3_765 ? 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 C19 Cu1 C20 149.7(2) . . ? C19 Cu1 N1 101.14(17) . . ? C20 Cu1 N1 108.99(16) . . ? N6 Cu2 C20' 0.0(3) 8_755 8_755 ? N6 Cu2 C19' 152.85(19) 8_755 . ? C20' Cu2 C19' 152.85(19) 8_755 . ? N6 Cu2 N4 102.61(15) 8_755 3_745 ? C20' Cu2 N4 102.61(15) 8_755 3_745 ? C19' Cu2 N4 103.31(17) . 3_745 ? N1 C1 C2 123.2(5) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C1 C2 C3 118.3(5) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 119.6(5) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 118.9(5) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? N1 C5 C4 122.3(4) . . ? N1 C5 N2 115.8(4) . . ? C4 C5 N2 121.9(4) . . ? C7 C6 C7 118.2(6) . 3_755 ? C7 C6 N2 120.9(3) . . ? C7 C6 N2 120.9(3) 3_755 . ? C8 C7 C6 120.7(5) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 121.5(5) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C8 C9 C8 117.4(6) . 3_755 ? C8 C9 C10 121.3(3) . . ? C8 C9 C10 121.3(3) 3_755 . ? C11 C10 C11 118.0(6) 3_755 . ? C11 C10 C9 121.0(3) 3_755 . ? C11 C10 C9 121.0(3) . . ? C10 C11 C12 120.9(5) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C13 C12 C11 120.9(5) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C12 118.3(5) . 3_755 ? C12 C13 N3 120.8(3) . . ? C12 C13 N3 120.8(3) 3_755 . ? N4 C14 C15 122.9(4) . . ? N4 C14 N3 115.3(4) . . ? C15 C14 N3 121.8(4) . . ? C16 C15 C14 118.4(5) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? C17 C16 C15 119.4(5) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C18 C17 C16 118.3(5) . . ? C18 C17 H17 120.9 . . ? C16 C17 H17 120.9 . . ? N4 C18 C17 124.2(5) . . ? N4 C18 H18 117.9 . . ? C17 C18 H18 117.9 . . ? C19' C19 Cu1 173.8(5) . . ? C19 C19' Cu2 172.0(5) . . ? C20' C20 Cu1 176.0(4) . . ? C20 C20' Cu2 171.9(4) . 8_765 ? C5 N1 C1 117.4(4) . . ? C5 N1 Cu1 124.8(3) . . ? C1 N1 Cu1 112.9(3) . . ? C5 N2 C5 118.6(4) 3_755 . ? C5 N2 C6 120.7(2) 3_755 . ? C5 N2 C6 120.7(2) . . ? C14 N3 C14 118.6(4) 3_755 . ? C14 N3 C13 120.7(2) 3_755 . ? C14 N3 C13 120.7(2) . . ? C14 N4 C18 116.7(4) . . ? C14 N4 Cu2 124.5(3) . 3_765 ? C18 N4 Cu2 116.0(3) . 3_765 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -1.1(8) . . . . ? C1 C2 C3 C4 4.8(8) . . . . ? C2 C3 C4 C5 -3.5(8) . . . . ? C3 C4 C5 N1 -1.7(7) . . . . ? C3 C4 C5 N2 177.9(4) . . . . ? C7 C6 C7 C8 1.4(4) 3_755 . . . ? N2 C6 C7 C8 -178.6(4) . . . . ? C6 C7 C8 C9 -2.9(9) . . . . ? C7 C8 C9 C8 1.4(4) . . . 3_755 ? C7 C8 C9 C10 -178.6(4) . . . . ? C8 C9 C10 C11 121.0(4) . . . 3_755 ? C8 C9 C10 C11 -59.0(4) 3_755 . . 3_755 ? C8 C9 C10 C11 -59.0(4) . . . . ? C8 C9 C10 C11 121.0(4) 3_755 . . . ? C11 C10 C11 C12 1.2(3) 3_755 . . . ? C9 C10 C11 C12 -178.8(3) . . . . ? C10 C11 C12 C13 -2.5(7) . . . . ? C11 C12 C13 C12 1.2(3) . . . 3_755 ? C11 C12 C13 N3 -178.8(3) . . . . ? N4 C14 C15 C16 0.7(7) . . . . ? N3 C14 C15 C16 -180.0(4) . . . . ? C14 C15 C16 C17 -2.2(8) . . . . ? C15 C16 C17 C18 1.2(9) . . . . ? C16 C17 C18 N4 1.5(10) . . . . ? C20 Cu1 C19 C19' -141(5) . . . . ? N1 Cu1 C19 C19' 45(5) . . . . ? Cu1 C19 C19' Cu2 33(8) . . . . ? N6 Cu2 C19' C19 146(3) 8_755 . . . ? C20' Cu2 C19' C19 146(3) 8_755 . . . ? N4 Cu2 C19' C19 -17(3) 3_745 . . . ? C19 Cu1 C20 C20' 128(6) . . . . ? N1 Cu1 C20 C20' -59(6) . . . . ? Cu1 C20 C20' Cu2 -3(9) . . . 8_765 ? C4 C5 N1 C1 5.3(6) . . . . ? N2 C5 N1 C1 -174.4(4) . . . . ? C4 C5 N1 Cu1 -148.0(4) . . . . ? N2 C5 N1 Cu1 32.4(5) . . . . ? C2 C1 N1 C5 -3.9(7) . . . . ? C2 C1 N1 Cu1 152.5(4) . . . . ? C19 Cu1 N1 C5 -160.1(4) . . . . ? C20 Cu1 N1 C5 23.3(4) . . . . ? C19 Cu1 N1 C1 45.6(4) . . . . ? C20 Cu1 N1 C1 -131.0(3) . . . . ? N1 C5 N2 C5 40.2(3) . . . 3_755 ? C4 C5 N2 C5 -139.4(5) . . . 3_755 ? N1 C5 N2 C6 -139.8(3) . . . . ? C4 C5 N2 C6 40.6(5) . . . . ? C7 C6 N2 C5 31.6(4) . . . 3_755 ? C7 C6 N2 C5 -148.4(4) 3_755 . . 3_755 ? C7 C6 N2 C5 -148.4(4) . . . . ? C7 C6 N2 C5 31.6(4) 3_755 . . . ? N4 C14 N3 C14 46.6(3) . . . 3_755 ? C15 C14 N3 C14 -132.8(5) . . . 3_755 ? N4 C14 N3 C13 -133.4(3) . . . . ? C15 C14 N3 C13 47.2(5) . . . . ? C12 C13 N3 C14 32.6(3) . . . 3_755 ? C12 C13 N3 C14 -147.4(3) 3_755 . . 3_755 ? C12 C13 N3 C14 -147.4(3) . . . . ? C12 C13 N3 C14 32.6(3) 3_755 . . . ? C15 C14 N4 C18 1.8(7) . . . . ? N3 C14 N4 C18 -177.6(4) . . . . ? C15 C14 N4 Cu2 -158.7(4) . . . 3_765 ? N3 C14 N4 Cu2 21.9(5) . . . 3_765 ? C17 C18 N4 C14 -3.0(8) . . . . ? C17 C18 N4 Cu2 159.2(5) . . . 3_765 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.682 _refine_diff_density_min -0.999 _refine_diff_density_rms 0.078 #===END data_7 _database_code_depnum_ccdc_archive 'CCDC 773761' #TrackingRef '- 1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H7 Cu2 N3.50 O0.50' _chemical_formula_weight 311.27 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnnn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x+1/2, y, -z+1/2' 'x, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x-1/2, -y, z-1/2' '-x, y-1/2, z-1/2' _cell_length_a 7.413(4) _cell_length_b 8.577(4) _cell_length_c 37.051(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2355.8(19) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.755 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1228 _exptl_absorpt_coefficient_mu 3.588 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5645 _exptl_absorpt_correction_T_max 0.6527 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _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 APEX area-dectector diffractometer' _diffrn_measurement_method '\f and \w-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5964 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0609 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2026 _reflns_number_gt 1492 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material SHELXL-97 _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^)+(0.0303P)^2^+24.3185P] 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 2026 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0940 _refine_ls_R_factor_gt 0.0739 _refine_ls_wR_factor_ref 0.1727 _refine_ls_wR_factor_gt 0.1618 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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 1.02487(15) 0.42626(14) 0.43616(2) 0.0535(4) Uani 1 1 d . . . Cu2 Cu 1.1939(3) 0.5485(2) 0.31378(3) 0.1018(7) Uani 1 1 d . . . C1 C 1.0270(12) 0.0894(12) 0.4532(2) 0.057(2) Uani 1 1 d . . . H1 H 1.0873 0.1254 0.4735 0.069 Uiso 1 1 calc R . . C2 C 1.0292(13) -0.0663(13) 0.4461(2) 0.064(3) Uani 1 1 d . . . H2 H 1.0892 -0.1348 0.4614 0.077 Uiso 1 1 calc R . . C3 C 0.9412(13) -0.1206(11) 0.4160(3) 0.061(2) Uani 1 1 d . . . H3 H 0.9454 -0.2258 0.4101 0.073 Uiso 1 1 calc R . . C4 C 0.8467(12) -0.0174(10) 0.3947(2) 0.049(2) Uani 1 1 d . . . H4 H 0.7834 -0.0516 0.3746 0.058 Uiso 1 1 calc R . . C5 C 0.8487(10) 0.1379(9) 0.40416(17) 0.0384(18) Uani 1 1 d . . . C6 C 0.7500 0.2500 0.3458(3) 0.044(3) Uani 1 2 d S . . C7 C 0.9058(11) 0.2167(11) 0.32701(18) 0.049(2) Uani 1 1 d . . . H7 H 1.0120 0.1946 0.3394 0.059 Uiso 1 1 calc R . . C8 C 0.9034(12) 0.2163(11) 0.28931(19) 0.051(2) Uani 1 1 d . . . H8 H 1.0088 0.1925 0.2768 0.061 Uiso 1 1 calc R . . C9 C 0.7500 0.2500 0.2702(2) 0.045(3) Uani 1 2 d S . . C10 C 1.1556(13) 0.5188(11) 0.36139(19) 0.053(2) Uani 1 1 d . . . C11 C 1.0054(12) 0.4846(11) 0.48511(19) 0.060(2) Uani 0.50 1 d P . . C12 C 1.2385(16) 0.5503(12) 0.2650(2) 0.081(3) Uani 0.50 1 d P . . N1 N 0.9428(9) 0.1923(8) 0.43235(14) 0.0421(16) Uani 1 1 d . . . N2 N 0.7500 0.2500 0.3844(2) 0.041(2) Uani 1 2 d S . . N3 N 1.1097(11) 0.4887(10) 0.3896(2) 0.068(2) Uani 1 1 d . . . N4 N 1.0054(12) 0.4846(11) 0.48511(19) 0.060(2) Uani 0.50 1 d P . . N5 N 1.2385(16) 0.5503(12) 0.2650(2) 0.081(3) Uani 0.50 1 d P . . O1 O 0.852(5) 0.751(5) 0.3023(8) 0.25(2) Uani 0.50 1 d P . . 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 0.0661(7) 0.0624(8) 0.0321(5) -0.0083(5) -0.0008(5) -0.0033(6) Cu2 0.1697(18) 0.0972(12) 0.0384(6) 0.0054(7) 0.0266(8) 0.0113(12) C1 0.063(5) 0.073(8) 0.036(4) 0.011(5) -0.007(4) 0.003(5) C2 0.064(6) 0.074(8) 0.055(5) 0.029(5) 0.000(4) 0.016(6) C3 0.065(6) 0.043(6) 0.074(6) 0.012(5) 0.010(5) 0.004(5) C4 0.061(5) 0.035(5) 0.050(5) -0.006(4) 0.003(4) -0.002(4) C5 0.050(4) 0.043(5) 0.023(3) 0.005(3) 0.003(3) 0.001(4) C6 0.068(8) 0.038(7) 0.026(5) 0.000 0.000 0.000(6) C7 0.054(5) 0.068(6) 0.024(3) -0.002(4) -0.001(3) 0.012(5) C8 0.057(5) 0.068(7) 0.027(3) -0.001(4) 0.010(4) 0.009(5) C9 0.071(8) 0.041(7) 0.024(5) 0.000 0.000 0.001(6) C10 0.082(6) 0.059(6) 0.020(3) 0.002(4) 0.012(4) -0.004(5) C11 0.076(6) 0.061(5) 0.043(4) -0.015(4) 0.000(4) -0.011(4) C12 0.125(8) 0.074(7) 0.043(4) 0.000(4) 0.016(6) 0.002(7) N1 0.057(4) 0.044(4) 0.025(3) 0.004(3) 0.000(3) -0.001(3) N2 0.057(6) 0.046(6) 0.020(4) 0.000 0.000 0.007(5) N3 0.074(5) 0.062(6) 0.067(5) -0.015(4) -0.011(4) -0.001(4) N4 0.076(6) 0.061(5) 0.043(4) -0.015(4) 0.000(4) -0.011(4) N5 0.125(8) 0.074(7) 0.043(4) 0.000(4) 0.016(6) 0.002(7) O1 0.31(5) 0.23(3) 0.20(2) 0.06(3) 0.14(3) 0.05(5) _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 C11 1.887(7) . ? Cu1 N3 1.912(9) . ? Cu1 N1 2.102(7) . ? Cu2 C10 1.805(7) . ? Cu2 C12 1.836(7) . ? C1 N1 1.328(11) . ? C1 C2 1.361(14) . ? C1 H1 0.9300 . ? C2 C3 1.373(14) . ? C2 H2 0.9300 . ? C3 C4 1.376(12) . ? C3 H3 0.9300 . ? C4 C5 1.377(11) . ? C4 H4 0.9300 . ? C5 N1 1.340(9) . ? C5 N2 1.412(8) . ? C6 C7 1.378(9) 2_655 ? C6 C7 1.378(9) . ? C6 N2 1.433(12) . ? C7 C8 1.397(9) . ? C7 H7 0.9300 . ? C8 C9 1.370(9) . ? C8 H8 0.9300 . ? C9 C8 1.370(9) 2_655 ? C9 C9 1.500(18) 3_655 ? C10 N3 1.130(10) . ? C11 N4 1.137(14) 5_766 ? C11 C11 1.137(14) 5_766 ? C12 N5 1.127(15) 3_755 ? C12 C12 1.127(15) 3_755 ? N2 C5 1.412(8) 2_655 ? O1 O1 1.52(7) 2_665 ? 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 C11 Cu1 N3 144.9(4) . . ? C11 Cu1 N1 107.2(3) . . ? N3 Cu1 N1 107.6(3) . . ? C10 Cu2 C12 172.3(4) . . ? N1 C1 C2 123.1(8) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 118.9(9) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 119.3(9) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 118.1(8) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? N1 C5 C4 122.7(7) . . ? N1 C5 N2 115.8(7) . . ? C4 C5 N2 121.5(7) . . ? C7 C6 C7 119.5(9) 2_655 . ? C7 C6 N2 120.3(5) 2_655 . ? C7 C6 N2 120.3(5) . . ? C6 C7 C8 119.6(8) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C9 C8 C7 121.7(8) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C8 C9 C8 117.9(9) . 2_655 ? C8 C9 C9 121.1(4) . 3_655 ? C8 C9 C9 121.1(4) 2_655 3_655 ? N3 C10 Cu2 169.9(9) . . ? N4 C11 C11 0.0(9) 5_766 5_766 ? N4 C11 Cu1 178.0(12) 5_766 . ? C11 C11 Cu1 178.0(12) 5_766 . ? N5 C12 C12 0.00(12) 3_755 3_755 ? N5 C12 Cu2 178.3(16) 3_755 . ? C12 C12 Cu2 178.3(16) 3_755 . ? C1 N1 C5 117.8(7) . . ? C1 N1 Cu1 117.4(6) . . ? C5 N1 Cu1 122.4(5) . . ? C5 N2 C5 117.7(8) 2_655 . ? C5 N2 C6 121.2(4) 2_655 . ? C5 N2 C6 121.2(4) . . ? C10 N3 Cu1 176.4(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.3(15) . . . . ? C1 C2 C3 C4 -2.9(14) . . . . ? C2 C3 C4 C5 1.7(13) . . . . ? C3 C4 C5 N1 2.1(12) . . . . ? C3 C4 C5 N2 -177.7(7) . . . . ? C7 C6 C7 C8 -0.4(6) 2_655 . . . ? N2 C6 C7 C8 179.6(6) . . . . ? C6 C7 C8 C9 0.7(13) . . . . ? C7 C8 C9 C8 -0.4(6) . . . 2_655 ? C7 C8 C9 C9 179.6(6) . . . 3_655 ? C12 Cu2 C10 N3 -68(7) . . . . ? N3 Cu1 C11 N4 -142(33) . . . 5_766 ? N1 Cu1 C11 N4 29(34) . . . 5_766 ? N3 Cu1 C11 C11 -142(33) . . . 5_766 ? N1 Cu1 C11 C11 29(34) . . . 5_766 ? C10 Cu2 C12 N5 83(22) . . . 3_755 ? C10 Cu2 C12 C12 83(22) . . . 3_755 ? C2 C1 N1 C5 3.4(13) . . . . ? C2 C1 N1 Cu1 -159.2(7) . . . . ? C4 C5 N1 C1 -4.6(11) . . . . ? N2 C5 N1 C1 175.3(7) . . . . ? C4 C5 N1 Cu1 157.0(6) . . . . ? N2 C5 N1 Cu1 -23.2(9) . . . . ? C11 Cu1 N1 C1 -55.4(7) . . . . ? N3 Cu1 N1 C1 119.5(6) . . . . ? C11 Cu1 N1 C5 142.9(6) . . . . ? N3 Cu1 N1 C5 -42.2(7) . . . . ? N1 C5 N2 C5 -44.0(5) . . . 2_655 ? C4 C5 N2 C5 135.8(8) . . . 2_655 ? N1 C5 N2 C6 136.0(5) . . . . ? C4 C5 N2 C6 -44.2(8) . . . . ? C7 C6 N2 C5 -38.8(6) 2_655 . . 2_655 ? C7 C6 N2 C5 141.2(6) . . . 2_655 ? C7 C6 N2 C5 141.2(6) 2_655 . . . ? C7 C6 N2 C5 -38.8(6) . . . . ? Cu2 C10 N3 Cu1 28(19) . . . . ? C11 Cu1 N3 C10 -174(14) . . . . ? N1 Cu1 N3 C10 15(14) . . . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 2.030 _refine_diff_density_min -1.003 _refine_diff_density_rms 0.127 #===END data_8 _database_code_depnum_ccdc_archive 'CCDC 773762' #TrackingRef '- 1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 Cu I N5' _chemical_formula_weight 566.87 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 9.7052(8) _cell_length_b 15.6248(12) _cell_length_c 30.199(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.2010(10) _cell_angle_gamma 90.00 _cell_volume 4560.5(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2232 _exptl_absorpt_coefficient_mu 2.332 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.1038 _exptl_absorpt_correction_T_max 0.2732 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _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 APEX area-dectector diffractometer' _diffrn_measurement_method '\f and \w-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17020 _diffrn_reflns_av_R_equivalents 0.0594 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4007 _reflns_number_gt 2741 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material SHELXL-97 _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^)+(0.0284P)^2^+9.4546P] 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 4007 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.0985 _refine_ls_wR_factor_gt 0.0940 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.58719(7) 0.05321(5) 0.48565(2) 0.0741(2) Uani 1 1 d . . . C1 C 0.5329(7) 0.2215(4) 0.52483(18) 0.0743(16) Uani 1 1 d . . . H1 H 0.5611 0.2000 0.5529 0.089 Uiso 1 1 calc R . . C2 C 0.4349(9) 0.2780(5) 0.5214(2) 0.105(2) Uani 1 1 d . . . H2 H 0.3966 0.2981 0.5466 0.126 Uiso 1 1 calc R . . C3 C 0.3888(9) 0.3074(5) 0.4799(3) 0.125(3) Uani 1 1 d . . . H3 H 0.3128 0.3438 0.4761 0.150 Uiso 1 1 calc R . . C4 C 0.4574(7) 0.2821(4) 0.44396(19) 0.094(2) Uani 1 1 d . . . H4 H 0.4304 0.3028 0.4156 0.112 Uiso 1 1 calc R . . C5 C 0.5654(5) 0.2264(3) 0.45074(15) 0.0554(13) Uani 1 1 d . . . C6 C 0.7371(5) 0.1368(3) 0.41478(16) 0.0580(13) Uani 1 1 d . . . C7 C 0.8365(6) 0.1412(4) 0.38468(17) 0.0714(15) Uani 1 1 d . . . H7 H 0.8345 0.1858 0.3642 0.086 Uiso 1 1 calc R . . C8 C 0.9364(7) 0.0808(5) 0.3850(2) 0.092(2) Uani 1 1 d . . . H8 H 0.9989 0.0809 0.3634 0.110 Uiso 1 1 calc R . . C9 C 0.9445(7) 0.0188(5) 0.4178(3) 0.106(2) Uani 1 1 d . . . H9 H 1.0155 -0.0213 0.4201 0.127 Uiso 1 1 calc R . . C10 C 0.8430(7) 0.0190(5) 0.4468(3) 0.113(3) Uani 1 1 d . . . H10 H 0.8478 -0.0220 0.4692 0.135 Uiso 1 1 calc R . . C11 C 0.6009(5) 0.2435(4) 0.37210(14) 0.0582(13) Uani 1 1 d . . . C12 C 0.5122(6) 0.2055(4) 0.34008(16) 0.0713(15) Uani 1 1 d . . . H12 H 0.4741 0.1523 0.3454 0.086 Uiso 1 1 calc R . . C13 C 0.4792(6) 0.2463(4) 0.29956(16) 0.0728(16) Uani 1 1 d . . . H13 H 0.4192 0.2197 0.2780 0.087 Uiso 1 1 calc R . . C14 C 0.5327(6) 0.3240(4) 0.29080(14) 0.0635(14) Uani 1 1 d . . . C15 C 0.6192(6) 0.3629(4) 0.32400(15) 0.0690(15) Uani 1 1 d . . . H15 H 0.6554 0.4167 0.3190 0.083 Uiso 1 1 calc R . . C16 C 0.6523(6) 0.3234(4) 0.36399(16) 0.0697(15) Uani 1 1 d . . . H16 H 0.7099 0.3508 0.3858 0.084 Uiso 1 1 calc R . . C17 C 0.5000 0.4586(5) 0.2500 0.067(2) Uani 1 2 d S . . C18 C 0.3999(7) 0.5035(4) 0.26962(18) 0.0789(17) Uani 1 1 d . . . H18 H 0.3320 0.4742 0.2833 0.095 Uiso 1 1 calc R . . C19 C 0.3994(7) 0.5919(4) 0.26910(17) 0.0774(16) Uani 1 1 d . . . H19 H 0.3301 0.6216 0.2819 0.093 Uiso 1 1 calc R . . C20 C 0.5000 0.6358(5) 0.2500 0.069(2) Uani 1 2 d S . . C21 C 0.5360(6) 0.7715(4) 0.29029(17) 0.0723(16) Uani 1 1 d . . . C22 C 0.4836(8) 0.8500(5) 0.2977(2) 0.098(2) Uani 1 1 d . . . H22 H 0.4219 0.8766 0.2767 0.118 Uiso 1 1 calc R . . C23 C 0.5252(10) 0.8884(5) 0.3373(3) 0.120(3) Uani 1 1 d . . . H23 H 0.4914 0.9424 0.3433 0.144 Uiso 1 1 calc R . . C24 C 0.6142(9) 0.8497(7) 0.3679(3) 0.118(3) Uani 1 1 d . . . H24 H 0.6443 0.8772 0.3943 0.141 Uiso 1 1 calc R . . C25 C 0.6589(8) 0.7693(6) 0.3591(2) 0.110(3) Uani 1 1 d . . . H25 H 0.7166 0.7412 0.3806 0.132 Uiso 1 1 calc R . . I1 I 0.34788(4) 0.02272(3) 0.440196(12) 0.07646(19) Uani 1 1 d . . . N1 N 0.5956(5) 0.1926(3) 0.49026(14) 0.0726(13) Uani 1 1 d . . . N2 N 0.6347(4) 0.1995(3) 0.41408(12) 0.0592(11) Uani 1 1 d . . . N3 N 0.7377(5) 0.0748(3) 0.44481(16) 0.0754(13) Uani 1 1 d . . . N4 N 0.5000 0.3667(4) 0.2500 0.077(2) Uani 1 2 d S . . N5 N 0.5000 0.7278(5) 0.2500 0.0790(19) Uani 1 2 d S . . N6 N 0.6225(6) 0.7285(4) 0.31998(16) 0.0895(16) 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 0.0733(5) 0.0632(5) 0.0876(5) 0.0160(4) 0.0178(4) -0.0023(4) C1 0.100(5) 0.072(4) 0.052(3) 0.000(3) 0.009(3) -0.009(4) C2 0.160(8) 0.089(5) 0.070(4) -0.006(4) 0.042(4) 0.007(5) C3 0.152(7) 0.109(6) 0.123(6) 0.038(5) 0.066(6) 0.055(6) C4 0.112(5) 0.107(5) 0.065(4) 0.033(4) 0.028(4) 0.040(4) C5 0.071(4) 0.049(3) 0.047(3) 0.000(2) 0.005(2) -0.002(3) C6 0.059(3) 0.060(3) 0.054(3) -0.004(3) 0.002(3) -0.002(3) C7 0.071(4) 0.087(4) 0.058(3) -0.007(3) 0.017(3) -0.003(3) C8 0.077(5) 0.112(6) 0.091(5) -0.018(4) 0.031(4) 0.005(4) C9 0.071(5) 0.088(5) 0.161(7) -0.007(5) 0.030(5) 0.017(4) C10 0.082(5) 0.091(6) 0.170(8) 0.029(5) 0.041(5) 0.018(4) C11 0.070(3) 0.067(4) 0.038(2) 0.000(2) 0.008(2) -0.001(3) C12 0.089(4) 0.076(4) 0.049(3) 0.002(3) 0.003(3) -0.021(3) C13 0.090(4) 0.080(4) 0.047(3) -0.002(3) -0.005(3) -0.019(3) C14 0.080(4) 0.072(4) 0.039(3) 0.003(2) 0.006(2) -0.007(3) C15 0.090(4) 0.064(3) 0.052(3) 0.007(3) 0.001(3) -0.023(3) C16 0.087(4) 0.071(4) 0.050(3) 0.005(3) -0.003(3) -0.018(3) C17 0.098(6) 0.068(6) 0.036(3) 0.000 0.003(4) 0.000 C18 0.092(5) 0.089(5) 0.058(3) -0.006(3) 0.020(3) -0.018(4) C19 0.089(4) 0.086(5) 0.058(3) -0.010(3) 0.016(3) 0.007(4) C20 0.100(7) 0.064(5) 0.043(4) 0.000 0.008(4) 0.000 C21 0.086(4) 0.083(4) 0.050(3) -0.001(3) 0.015(3) -0.009(3) C22 0.131(6) 0.090(5) 0.074(4) -0.017(4) 0.007(4) 0.022(4) C23 0.159(9) 0.095(6) 0.109(6) -0.021(5) 0.037(6) 0.008(5) C24 0.123(7) 0.145(8) 0.087(5) -0.056(6) 0.018(5) -0.027(6) C25 0.104(6) 0.149(8) 0.075(4) -0.008(5) -0.004(4) -0.020(5) I1 0.0757(3) 0.0717(3) 0.0778(3) 0.00963(18) -0.0159(2) -0.00872(19) N1 0.098(4) 0.069(3) 0.051(3) 0.007(2) 0.009(2) 0.011(3) N2 0.070(3) 0.064(3) 0.045(2) 0.0037(19) 0.0135(19) 0.003(2) N3 0.065(3) 0.059(3) 0.107(4) 0.016(3) 0.031(3) 0.011(3) N4 0.111(6) 0.082(5) 0.036(3) 0.000 -0.001(3) 0.000 N5 0.106(6) 0.083(5) 0.046(3) 0.000 -0.002(3) 0.000 N6 0.092(4) 0.114(4) 0.062(3) -0.011(3) 0.003(3) -0.006(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 2.024(4) . ? Cu1 N1 2.183(5) . ? Cu1 I1 2.5619(8) 5_656 ? Cu1 Cu1 2.5780(14) 5_656 ? Cu1 I1 2.6320(8) . ? C1 C2 1.294(9) . ? C1 N1 1.335(7) . ? C1 H1 0.9300 . ? C2 C3 1.372(10) . ? C2 H2 0.9300 . ? C3 C4 1.382(9) . ? C3 H3 0.9300 . ? C4 C5 1.364(7) . ? C4 H4 0.9300 . ? C5 N1 1.314(6) . ? C5 N2 1.410(6) . ? C6 N3 1.327(6) . ? C6 C7 1.386(7) . ? C6 N2 1.395(6) . ? C7 C8 1.353(9) . ? C7 H7 0.9300 . ? C8 C9 1.381(10) . ? C8 H8 0.9300 . ? C9 C10 1.377(10) . ? C9 H9 0.9300 . ? C10 N3 1.340(8) . ? C10 H10 0.9300 . ? C11 C12 1.370(7) . ? C11 C16 1.374(7) . ? C11 N2 1.453(6) . ? C12 C13 1.391(7) . ? C12 H12 0.9300 . ? C13 C14 1.356(7) . ? C13 H13 0.9300 . ? C14 C15 1.388(7) . ? C14 N4 1.412(6) . ? C15 C16 1.368(7) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.376(7) 2_655 ? C17 C18 1.376(7) . ? C17 N4 1.435(10) . ? C18 C19 1.380(8) . ? C18 H18 0.9300 . ? C19 C20 1.364(7) . ? C19 H19 0.9300 . ? C20 C19 1.364(7) 2_655 ? C20 N5 1.437(10) . ? C21 N6 1.351(7) . ? C21 C22 1.353(8) . ? C21 N5 1.412(6) . ? C22 C23 1.365(10) . ? C22 H22 0.9300 . ? C23 C24 1.350(11) . ? C23 H23 0.9300 . ? C24 C25 1.363(11) . ? C24 H24 0.9300 . ? C25 N6 1.360(8) . ? C25 H25 0.9300 . ? I1 Cu1 2.5619(8) 5_656 ? N4 C14 1.412(6) 2_655 ? N5 C21 1.412(6) 2_655 ? 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 81.24(18) . . ? N3 Cu1 I1 118.41(14) . 5_656 ? N1 Cu1 I1 113.66(11) . 5_656 ? N3 Cu1 Cu1 147.62(15) . 5_656 ? N1 Cu1 Cu1 130.09(13) . 5_656 ? I1 Cu1 Cu1 61.60(3) 5_656 5_656 ? N3 Cu1 I1 111.35(15) . . ? N1 Cu1 I1 103.89(12) . . ? I1 Cu1 I1 120.50(3) 5_656 . ? Cu1 Cu1 I1 58.90(3) 5_656 . ? C2 C1 N1 123.6(6) . . ? C2 C1 H1 118.2 . . ? N1 C1 H1 118.2 . . ? C1 C2 C3 118.5(6) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C2 C3 C4 118.8(7) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 118.9(6) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? N1 C5 C4 119.9(5) . . ? N1 C5 N2 120.7(5) . . ? C4 C5 N2 119.1(4) . . ? N3 C6 C7 121.7(5) . . ? N3 C6 N2 118.9(5) . . ? C7 C6 N2 119.5(5) . . ? C8 C7 C6 120.0(6) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 119.3(6) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 117.2(7) . . ? C10 C9 H9 121.4 . . ? C8 C9 H9 121.4 . . ? N3 C10 C9 124.0(7) . . ? N3 C10 H10 118.0 . . ? C9 C10 H10 118.0 . . ? C12 C11 C16 118.9(4) . . ? C12 C11 N2 119.2(5) . . ? C16 C11 N2 121.9(4) . . ? C11 C12 C13 120.1(5) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 121.3(5) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C15 117.9(4) . . ? C13 C14 N4 122.3(5) . . ? C15 C14 N4 119.8(5) . . ? C16 C15 C14 121.2(5) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C11 120.5(5) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C18 C17 C18 118.6(8) 2_655 . ? C18 C17 N4 120.7(4) 2_655 . ? C18 C17 N4 120.7(4) . . ? C17 C18 C19 120.5(6) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C20 C19 C18 120.5(6) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C19 119.5(8) . 2_655 ? C19 C20 N5 120.3(4) . . ? C19 C20 N5 120.3(4) 2_655 . ? N6 C21 C22 124.2(5) . . ? N6 C21 N5 114.9(5) . . ? C22 C21 N5 120.9(6) . . ? C21 C22 C23 117.2(7) . . ? C21 C22 H22 121.4 . . ? C23 C22 H22 121.4 . . ? C24 C23 C22 121.6(8) . . ? C24 C23 H23 119.2 . . ? C22 C23 H23 119.2 . . ? C23 C24 C25 118.2(7) . . ? C23 C24 H24 120.9 . . ? C25 C24 H24 120.9 . . ? N6 C25 C24 122.7(7) . . ? N6 C25 H25 118.7 . . ? C24 C25 H25 118.7 . . ? Cu1 I1 Cu1 59.50(3) 5_656 . ? C5 N1 C1 119.6(5) . . ? C5 N1 Cu1 109.8(3) . . ? C1 N1 Cu1 111.8(4) . . ? C6 N2 C5 125.9(4) . . ? C6 N2 C11 116.7(4) . . ? C5 N2 C11 117.3(4) . . ? C6 N3 C10 117.5(5) . . ? C6 N3 Cu1 125.4(4) . . ? C10 N3 Cu1 117.0(4) . . ? C14 N4 C14 123.6(7) 2_655 . ? C14 N4 C17 118.2(3) 2_655 . ? C14 N4 C17 118.2(3) . . ? C21 N5 C21 122.1(7) . 2_655 ? C21 N5 C20 119.0(4) . . ? C21 N5 C20 119.0(4) 2_655 . ? C21 N6 C25 116.1(6) . . ? 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 2.7(12) . . . . ? C1 C2 C3 C4 -6.2(12) . . . . ? C2 C3 C4 C5 2.3(12) . . . . ? C3 C4 C5 N1 5.3(10) . . . . ? C3 C4 C5 N2 179.2(6) . . . . ? N3 C6 C7 C8 0.9(8) . . . . ? N2 C6 C7 C8 180.0(5) . . . . ? C6 C7 C8 C9 -5.1(10) . . . . ? C7 C8 C9 C10 4.3(11) . . . . ? C8 C9 C10 N3 0.6(13) . . . . ? C16 C11 C12 C13 2.2(9) . . . . ? N2 C11 C12 C13 -179.6(5) . . . . ? C11 C12 C13 C14 -0.3(9) . . . . ? C12 C13 C14 C15 -1.5(9) . . . . ? C12 C13 C14 N4 -179.7(5) . . . . ? C13 C14 C15 C16 1.5(9) . . . . ? N4 C14 C15 C16 179.6(5) . . . . ? C14 C15 C16 C11 0.5(9) . . . . ? C12 C11 C16 C15 -2.3(9) . . . . ? N2 C11 C16 C15 179.6(5) . . . . ? C18 C17 C18 C19 0.7(4) 2_655 . . . ? N4 C17 C18 C19 -179.3(4) . . . . ? C17 C18 C19 C20 -1.5(8) . . . . ? C18 C19 C20 C19 0.7(4) . . . 2_655 ? C18 C19 C20 N5 -179.3(4) . . . . ? N6 C21 C22 C23 2.1(11) . . . . ? N5 C21 C22 C23 -179.1(6) . . . . ? C21 C22 C23 C24 -0.3(12) . . . . ? C22 C23 C24 C25 -2.2(14) . . . . ? C23 C24 C25 N6 3.1(13) . . . . ? N3 Cu1 I1 Cu1 145.40(15) . . . 5_656 ? N1 Cu1 I1 Cu1 -128.72(13) . . . 5_656 ? I1 Cu1 I1 Cu1 0.0 5_656 . . 5_656 ? C4 C5 N1 C1 -9.0(8) . . . . ? N2 C5 N1 C1 177.2(5) . . . . ? C4 C5 N1 Cu1 122.2(5) . . . . ? N2 C5 N1 Cu1 -51.6(5) . . . . ? C2 C1 N1 C5 5.1(9) . . . . ? C2 C1 N1 Cu1 -125.2(6) . . . . ? N3 Cu1 N1 C5 60.7(4) . . . . ? I1 Cu1 N1 C5 178.0(3) 5_656 . . . ? Cu1 Cu1 N1 C5 -110.1(3) 5_656 . . . ? I1 Cu1 N1 C5 -49.3(4) . . . . ? N3 Cu1 N1 C1 -164.1(4) . . . . ? I1 Cu1 N1 C1 -46.8(4) 5_656 . . . ? Cu1 Cu1 N1 C1 25.1(5) 5_656 . . . ? I1 Cu1 N1 C1 86.0(4) . . . . ? N3 C6 N2 C5 27.3(7) . . . . ? C7 C6 N2 C5 -151.7(5) . . . . ? N3 C6 N2 C11 -155.4(5) . . . . ? C7 C6 N2 C11 25.5(7) . . . . ? N1 C5 N2 C6 0.7(8) . . . . ? C4 C5 N2 C6 -173.2(5) . . . . ? N1 C5 N2 C11 -176.6(5) . . . . ? C4 C5 N2 C11 9.6(7) . . . . ? C12 C11 N2 C6 81.7(6) . . . . ? C16 C11 N2 C6 -100.2(6) . . . . ? C12 C11 N2 C5 -100.8(6) . . . . ? C16 C11 N2 C5 77.3(6) . . . . ? C7 C6 N3 C10 3.8(8) . . . . ? N2 C6 N3 C10 -175.2(6) . . . . ? C7 C6 N3 Cu1 -172.5(4) . . . . ? N2 C6 N3 Cu1 8.4(7) . . . . ? C9 C10 N3 C6 -4.6(11) . . . . ? C9 C10 N3 Cu1 172.0(7) . . . . ? N1 Cu1 N3 C6 -42.0(5) . . . . ? I1 Cu1 N3 C6 -154.2(4) 5_656 . . . ? Cu1 Cu1 N3 C6 124.8(4) 5_656 . . . ? I1 Cu1 N3 C6 59.6(5) . . . . ? N1 Cu1 N3 C10 141.7(6) . . . . ? I1 Cu1 N3 C10 29.4(6) 5_656 . . . ? Cu1 Cu1 N3 C10 -51.6(7) 5_656 . . . ? I1 Cu1 N3 C10 -116.8(5) . . . . ? C13 C14 N4 C14 -30.3(4) . . . 2_655 ? C15 C14 N4 C14 151.6(6) . . . 2_655 ? C13 C14 N4 C17 149.7(4) . . . . ? C15 C14 N4 C17 -28.4(6) . . . . ? C18 C17 N4 C14 -69.6(4) 2_655 . . 2_655 ? C18 C17 N4 C14 110.4(4) . . . 2_655 ? C18 C17 N4 C14 110.4(4) 2_655 . . . ? C18 C17 N4 C14 -69.6(4) . . . . ? N6 C21 N5 C21 -152.2(6) . . . 2_655 ? C22 C21 N5 C21 28.9(5) . . . 2_655 ? N6 C21 N5 C20 27.8(5) . . . . ? C22 C21 N5 C20 -151.1(5) . . . . ? C19 C20 N5 C21 72.0(4) . . . . ? C19 C20 N5 C21 -108.0(4) 2_655 . . . ? C19 C20 N5 C21 -108.0(4) . . . 2_655 ? C19 C20 N5 C21 72.0(4) 2_655 . . 2_655 ? C22 C21 N6 C25 -1.2(9) . . . . ? N5 C21 N6 C25 179.9(5) . . . . ? C24 C25 N6 C21 -1.5(10) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.211 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.075 #===END