# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_fa2sh _database_code_depnum_ccdc_archive 'CCDC 892245' #TrackingRef 'FA2SH edit.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-Bis(2,5-dibromopyridine)dibromocopper(II) ; _chemical_name_common trans-Bis(2,5-dibromopyridine)dibromocopper(ii) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H6 Br6 Cu N2' _chemical_formula_weight 697.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3071(10) _cell_length_b 8.0751(14) _cell_length_c 8.5714(11) _cell_angle_alpha 104.521(13) _cell_angle_beta 94.539(10) _cell_angle_gamma 102.964(11) _cell_volume 407.57(11) _cell_formula_units_Z 1 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 23 _cell_measurement_theta_min 4.96 _cell_measurement_theta_max 18.06 _exptl_crystal_description Parallelpiped _exptl_crystal_colour Light_Brown-Green _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.840 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 319 _exptl_absorpt_coefficient_mu 16.031 _exptl_absorpt_correction_type 'Psi scan' _exptl_absorpt_correction_T_min 0.2743 _exptl_absorpt_correction_T_max 0.7477 _exptl_absorpt_process_details 'XPREP,Bruker SHELXTL v. 5.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'no decay was observed' _diffrn_reflns_number 1836 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1420 _reflns_number_gt 1187 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'XS, Bruker SHELXTL v. 5.10' _computing_structure_refinement 'XL, Bruker SHELXTL v. 5.10' _computing_molecular_graphics 'XP, Bruker SHELXTL v. 5.10' _computing_publication_material 'XCIF, Bruker SHELXTL v. 5.10' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0839P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.006(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1420 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1172 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 Cu Cu -1.5000 0.0000 0.0000 0.0312(3) Uani 1 2 d S . . Br Br -1.62657(12) 0.24024(10) 0.16182(9) 0.0437(3) Uani 1 1 d . . . Br2 Br -1.13088(11) 0.03514(11) 0.28167(10) 0.0471(3) Uani 1 1 d . . . Br5 Br -2.08984(13) -0.47299(10) 0.25422(11) 0.0536(3) Uani 1 1 d . . . N1 N -1.5609(9) -0.1295(7) 0.1653(7) 0.0310(12) Uani 1 1 d . . . C2 C -1.4078(11) -0.1135(9) 0.2868(8) 0.0359(15) Uani 1 1 d . . . C6 C -1.7620(10) -0.2359(9) 0.1609(9) 0.0355(15) Uani 1 1 d . . . H6A H -1.8734 -0.2478 0.0779 0.043 Uiso 1 1 calc R . . C3 C -1.4395(13) -0.1989(10) 0.4042(9) 0.0437(17) Uani 1 1 d . . . H3A H -1.3263 -0.1831 0.4872 0.052 Uiso 1 1 calc R . . C5 C -1.8060(11) -0.3258(9) 0.2741(9) 0.0375(16) Uani 1 1 d . . . C4 C -1.6443(13) -0.3099(9) 0.3977(9) 0.0413(17) Uani 1 1 d . . . H4A H -1.6714 -0.3719 0.4750 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu 0.0296(6) 0.0329(6) 0.0328(6) 0.0152(5) 0.0087(5) 0.0033(5) Br 0.0488(5) 0.0393(5) 0.0467(5) 0.0146(3) 0.0186(3) 0.0114(3) Br2 0.0337(4) 0.0515(5) 0.0541(5) 0.0202(4) 0.0025(3) 0.0017(3) Br5 0.0491(5) 0.0446(5) 0.0661(6) 0.0201(4) 0.0253(4) -0.0015(4) N1 0.033(3) 0.027(3) 0.032(3) 0.009(2) 0.010(2) 0.003(2) C2 0.036(3) 0.032(4) 0.040(4) 0.011(3) 0.009(3) 0.008(3) C6 0.031(3) 0.036(4) 0.039(4) 0.012(3) 0.011(3) 0.004(3) C3 0.047(4) 0.046(4) 0.041(4) 0.017(3) 0.004(3) 0.014(3) C5 0.037(3) 0.024(3) 0.053(4) 0.014(3) 0.022(3) 0.000(3) C4 0.060(4) 0.032(4) 0.039(4) 0.020(3) 0.018(3) 0.010(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 Cu N1 1.975(5) 2_255 ? Cu N1 1.975(5) . ? Cu Br 2.4177(8) . ? Cu Br 2.4177(8) 2_255 ? Br2 C2 1.895(7) . ? Br5 C5 1.882(6) . ? N1 C2 1.323(8) . ? N1 C6 1.354(8) . ? C2 C3 1.359(10) . ? C6 C5 1.361(10) . ? C3 C4 1.385(11) . ? C5 C4 1.372(11) . ? 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 Cu N1 180.0(2) 2_255 . ? N1 Cu Br 90.35(16) 2_255 . ? N1 Cu Br 89.65(16) . . ? N1 Cu Br 89.65(16) 2_255 2_255 ? N1 Cu Br 90.35(16) . 2_255 ? Br Cu Br 180.00(4) . 2_255 ? C2 N1 C6 117.2(6) . . ? C2 N1 Cu 121.3(4) . . ? C6 N1 Cu 121.5(4) . . ? N1 C2 C3 124.1(7) . . ? N1 C2 Br2 114.3(5) . . ? C3 C2 Br2 121.6(5) . . ? N1 C6 C5 122.0(6) . . ? C2 C3 C4 118.5(7) . . ? C6 C5 C4 120.0(6) . . ? C6 C5 Br5 118.5(6) . . ? C4 C5 Br5 121.5(5) . . ? C5 C4 C3 118.2(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 Br Cu N1 C2 -91.6(5) . . . . ? Br Cu N1 C2 88.4(5) 2_255 . . . ? Br Cu N1 C6 87.2(5) . . . . ? Br Cu N1 C6 -92.8(5) 2_255 . . . ? C6 N1 C2 C3 1.1(11) . . . . ? Cu N1 C2 C3 179.9(6) . . . . ? C6 N1 C2 Br2 179.2(5) . . . . ? Cu N1 C2 Br2 -1.9(7) . . . . ? C2 N1 C6 C5 -1.1(10) . . . . ? Cu N1 C6 C5 -180.0(5) . . . . ? N1 C2 C3 C4 0.0(12) . . . . ? Br2 C2 C3 C4 -178.0(6) . . . . ? N1 C6 C5 C4 0.1(11) . . . . ? N1 C6 C5 Br5 -178.9(5) . . . . ? C6 C5 C4 C3 1.0(11) . . . . ? Br5 C5 C4 C3 -180.0(6) . . . . ? C2 C3 C4 C5 -1.0(11) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.899 _refine_diff_density_min -0.949 _refine_diff_density_rms 0.184 data_fa4sh _database_code_depnum_ccdc_archive 'CCDC 892246' #TrackingRef 'FA4SH edited.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-Bis(2,5-dibromopyridine)dichlorocopper(II) ; _chemical_name_common trans-Bis(2,5-dibromopyridine)dichlorocopper(ii) _chemical_melting_point ? _chemical_formula_moiety C10H6N2Cl2Br4Cu _chemical_formula_sum 'C10 H6 Br4 Cl2 Cu N2' _chemical_formula_weight 608.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 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 8.3173(13) _cell_length_b 12.847(2) _cell_length_c 14.610(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.868(8) _cell_angle_gamma 90.00 _cell_volume 1560.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 39 _cell_measurement_theta_min 10.254 _cell_measurement_theta_max 24.919 _exptl_crystal_description Parallelpiped _exptl_crystal_colour Green _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1132 _exptl_absorpt_coefficient_mu 11.966 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.131 _exptl_absorpt_correction_T_max 0.340 _exptl_absorpt_process_details 'XPREP,Bruker SHELXTL v. 5.10' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 P4' _diffrn_measurement_method 'w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1827 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1357 _reflns_number_gt 1079 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'XS, Bruker SHELXTL v. 5.10' _computing_structure_refinement 'XL, Bruker SHELXTL v. 5.10' _computing_molecular_graphics 'XP, Bruker SHELXTL v. 5.10' _computing_publication_material 'XCIF, Bruker SHELXTL v. 5.10' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1020P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0032(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1357 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1429 _refine_ls_wR_factor_gt 0.1313 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 Br2 Br -0.14508(12) 0.08024(7) -0.15249(6) 0.0483(4) Uani 1 1 d . . . Cu Cu 0.0000 0.29185(9) -0.2500 0.0286(4) Uani 1 2 d S . . Cl1 Cl -0.2503(2) 0.35316(17) -0.24204(13) 0.0385(5) Uani 1 1 d . . . N1 N 0.0124(7) 0.2642(5) -0.1142(4) 0.0287(13) Uani 1 1 d . . . C6 C 0.0768(9) 0.3379(6) -0.0588(5) 0.0311(17) Uani 1 1 d . . . H16 H 0.1257 0.3956 -0.0850 0.037 Uiso 1 1 calc R . . C2 C -0.0571(9) 0.1828(6) -0.0750(5) 0.0317(17) Uani 1 1 d . . . C4 C -0.0009(10) 0.2464(7) 0.0742(5) 0.0386(19) Uani 1 1 d . . . H4 H -0.0074 0.2415 0.1375 0.046 Uiso 1 1 calc R . . C3 C -0.0649(11) 0.1690(6) 0.0187(5) 0.0401(19) Uani 1 1 d . . . H3 H -0.1115 0.1098 0.0435 0.048 Uiso 1 1 calc R . . Br5 Br 0.15628(11) 0.43779(7) 0.10791(5) 0.0436(4) Uani 1 1 d . . . C5 C 0.0724(9) 0.3305(6) 0.0346(5) 0.0310(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br2 0.0624(7) 0.0384(6) 0.0442(6) -0.0047(3) -0.0013(4) -0.0181(4) Cu 0.0342(8) 0.0250(7) 0.0266(7) 0.000 -0.0016(5) 0.000 Cl1 0.0369(12) 0.0413(11) 0.0374(10) -0.0002(8) 0.0009(8) 0.0060(9) N1 0.029(3) 0.029(3) 0.028(3) 0.004(3) -0.005(2) -0.002(3) C6 0.034(4) 0.023(4) 0.036(4) 0.006(3) 0.000(3) -0.002(3) C2 0.030(4) 0.029(4) 0.036(4) -0.001(3) 0.000(3) -0.004(3) C4 0.046(5) 0.038(4) 0.031(4) 0.014(4) 0.001(3) -0.007(4) C3 0.052(5) 0.030(4) 0.037(4) 0.008(3) -0.001(4) -0.005(4) Br5 0.0518(6) 0.0387(6) 0.0399(5) -0.0089(3) -0.0070(4) -0.0034(4) C5 0.027(4) 0.029(4) 0.036(4) 0.001(3) -0.005(3) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br2 C2 1.879(7) . ? Cu N1 2.016(6) . ? Cu N1 2.016(6) 2_554 ? Cu Cl1 2.230(2) 2_554 ? Cu Cl1 2.230(2) . ? N1 C2 1.330(9) . ? N1 C6 1.351(9) . ? C6 C5 1.370(10) . ? C2 C3 1.382(10) . ? C4 C5 1.372(10) . ? C4 C3 1.385(12) . ? Br5 C5 1.874(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu N1 159.7(4) . 2_554 ? N1 Cu Cl1 94.57(18) . 2_554 ? N1 Cu Cl1 92.56(18) 2_554 2_554 ? N1 Cu Cl1 92.56(18) . . ? N1 Cu Cl1 94.57(18) 2_554 . ? Cl1 Cu Cl1 138.64(13) 2_554 . ? C2 N1 C6 117.6(6) . . ? C2 N1 Cu 123.1(5) . . ? C6 N1 Cu 118.7(5) . . ? N1 C6 C5 122.2(7) . . ? N1 C2 C3 123.7(7) . . ? N1 C2 Br2 117.4(5) . . ? C3 C2 Br2 118.9(6) . . ? C5 C4 C3 119.2(7) . . ? C2 C3 C4 117.6(7) . . ? C6 C5 C4 119.6(7) . . ? C6 C5 Br5 120.2(6) . . ? C4 C5 Br5 120.1(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 Cu N1 C2 -33.1(6) 2_554 . . . ? Cl1 Cu N1 C2 -143.3(6) 2_554 . . . ? Cl1 Cu N1 C2 77.5(6) . . . . ? N1 Cu N1 C6 155.4(6) 2_554 . . . ? Cl1 Cu N1 C6 45.2(5) 2_554 . . . ? Cl1 Cu N1 C6 -94.0(5) . . . . ? C2 N1 C6 C5 0.2(11) . . . . ? Cu N1 C6 C5 172.2(6) . . . . ? C6 N1 C2 C3 -0.9(12) . . . . ? Cu N1 C2 C3 -172.5(6) . . . . ? C6 N1 C2 Br2 -179.6(5) . . . . ? Cu N1 C2 Br2 8.8(8) . . . . ? N1 C2 C3 C4 2.1(13) . . . . ? Br2 C2 C3 C4 -179.2(6) . . . . ? C5 C4 C3 C2 -2.5(13) . . . . ? N1 C6 C5 C4 -0.7(12) . . . . ? N1 C6 C5 Br5 -177.5(6) . . . . ? C3 C4 C5 C6 1.9(12) . . . . ? C3 C4 C5 Br5 178.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.224 _refine_diff_density_min -1.374 _refine_diff_density_rms 0.223