# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_C:1_173.CIF _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1_173 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 Br2 N2 Zn' _chemical_formula_weight 381.37 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' Zn Zn 0.2839 1.4301 '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 7.8183(10) _cell_length_b 9.0188(12) _cell_length_c 9.2659(14) _cell_angle_alpha 113.807(7) _cell_angle_beta 95.380(7) _cell_angle_gamma 95.722(6) _cell_volume 588.30(14) _cell_formula_units_Z 2 _cell_measurement_temperature 172(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.153 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 8.846 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2707 _exptl_absorpt_correction_T_max 0.2707 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 172(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7771 _diffrn_reflns_av_R_equivalents 0.1637 _diffrn_reflns_av_sigmaI/netI 0.1170 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 37.51 _reflns_number_total 4567 _reflns_number_gt 2713 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker)' _computing_cell_refinement 'APEX (Bruker)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour,2001;Atwood&Barbour,2003)' _computing_publication_material 'X-Seed (Barbour,2001;Atwood&Barbour,2003)' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4567 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2166 _refine_ls_R_factor_gt 0.1618 _refine_ls_wR_factor_ref 0.4944 _refine_ls_wR_factor_gt 0.4651 _refine_ls_goodness_of_fit_ref 1.695 _refine_ls_restrained_S_all 1.695 _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 Br1 Br 0.96060(19) 0.17964(19) 0.2102(2) 0.0325(5) Uani 1 1 d . . . Zn1 Zn 1.2342(2) 0.2866(2) 0.1789(3) 0.0263(5) Uani 1 1 d . . . Br2 Br 1.4743(2) 0.2155(2) 0.2927(3) 0.0353(5) Uani 1 1 d . . . N8 N 1.2809(16) 0.3012(15) -0.0295(17) 0.024(2) Uani 1 1 d . . . N2 N 1.2087(15) 0.5289(13) 0.2362(17) 0.024(2) Uani 1 1 d . . . C7 C 1.2662(17) 0.4484(17) -0.032(2) 0.024(2) Uani 1 1 d . . . C1 C 1.2220(17) 0.5750(16) 0.1185(19) 0.023(2) Uani 1 1 d . . . C6 C 1.186(2) 0.7305(19) 0.126(3) 0.035(4) Uani 1 1 d . . . H6 H 1.1822 0.7562 0.0362 0.042 Uiso 1 1 calc R . . C9 C 1.3250(18) 0.1825(18) -0.156(2) 0.028(3) Uani 1 1 d . . . H9 H 1.3334 0.0789 -0.1541 0.033 Uiso 1 1 calc R . . C3 C 1.174(2) 0.6370(18) 0.376(2) 0.031(3) Uani 1 1 d . . . H3 H 1.1675 0.6030 0.4599 0.037 Uiso 1 1 calc R . . C12 C 1.288(2) 0.480(2) -0.167(2) 0.031(3) Uani 1 1 d . . . H12 H 1.2683 0.5796 -0.1719 0.037 Uiso 1 1 calc R . . C4 C 1.147(2) 0.795(2) 0.404(2) 0.032(3) Uani 1 1 d . . . H4 H 1.1217 0.8681 0.5048 0.038 Uiso 1 1 calc R . . C10 C 1.359(2) 0.206(2) -0.292(2) 0.035(4) Uani 1 1 d . . . H10 H 1.3940 0.1224 -0.3807 0.042 Uiso 1 1 calc R . . C11 C 1.341(3) 0.356(2) -0.289(3) 0.040(4) Uani 1 1 d . . . H11 H 1.3658 0.3759 -0.3788 0.048 Uiso 1 1 calc R . . C5 C 1.157(3) 0.843(2) 0.277(3) 0.037(4) Uani 1 1 d . . . H5 H 1.1452 0.9518 0.2929 0.044 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 Br1 0.0198(6) 0.0471(8) 0.0457(11) 0.0337(8) 0.0102(7) 0.0041(5) Zn1 0.0193(7) 0.0358(8) 0.0354(11) 0.0262(7) 0.0063(7) 0.0041(5) Br2 0.0206(7) 0.0541(9) 0.0438(11) 0.0327(8) 0.0032(7) 0.0094(6) N8 0.017(5) 0.038(5) 0.020(6) 0.017(5) -0.008(5) -0.001(4) N2 0.017(5) 0.029(5) 0.030(7) 0.019(5) 0.000(5) 0.004(3) C7 0.012(4) 0.040(6) 0.024(7) 0.022(5) -0.011(5) -0.004(4) C1 0.013(5) 0.035(6) 0.024(7) 0.018(5) -0.007(5) -0.002(4) C6 0.034(8) 0.038(7) 0.051(12) 0.032(8) 0.014(8) 0.012(6) C9 0.016(5) 0.039(6) 0.033(9) 0.022(6) -0.001(6) -0.001(4) C3 0.035(8) 0.033(6) 0.034(9) 0.025(6) 0.004(7) 0.005(5) C12 0.025(7) 0.050(8) 0.027(9) 0.026(7) 0.006(6) 0.003(5) C4 0.026(7) 0.047(8) 0.030(9) 0.026(7) 0.000(7) 0.008(6) C10 0.029(8) 0.053(8) 0.023(9) 0.017(7) 0.004(7) 0.001(6) C11 0.032(8) 0.058(10) 0.039(12) 0.027(8) 0.011(9) 0.006(7) C5 0.039(9) 0.037(7) 0.045(11) 0.025(7) 0.009(9) 0.009(6) _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 Zn1 2.3498(19) . ? Zn1 N8 2.051(13) . ? Zn1 N2 2.066(10) . ? Zn1 Br2 2.337(2) . ? N8 C9 1.33(2) . ? N8 C7 1.353(17) . ? N2 C1 1.323(19) . ? N2 C3 1.34(2) . ? C7 C12 1.41(2) . ? C7 C1 1.50(2) . ? C1 C6 1.433(18) . ? C6 C5 1.41(3) . ? C9 C10 1.40(2) . ? C3 C4 1.38(2) . ? C12 C11 1.36(3) . ? C4 C5 1.42(3) . ? C10 C11 1.37(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N8 Zn1 N2 80.0(5) . . ? N8 Zn1 Br2 110.7(4) . . ? N2 Zn1 Br2 121.2(4) . . ? N8 Zn1 Br1 122.2(4) . . ? N2 Zn1 Br1 102.1(3) . . ? Br2 Zn1 Br1 115.94(8) . . ? C9 N8 C7 119.5(14) . . ? C9 N8 Zn1 126.1(10) . . ? C7 N8 Zn1 114.3(10) . . ? C1 N2 C3 119.0(11) . . ? C1 N2 Zn1 114.7(10) . . ? C3 N2 Zn1 126.3(9) . . ? N8 C7 C12 122.3(15) . . ? N8 C7 C1 115.2(13) . . ? C12 C7 C1 122.5(13) . . ? N2 C1 C6 123.6(15) . . ? N2 C1 C7 115.6(12) . . ? C6 C1 C7 120.6(14) . . ? C5 C6 C1 115.2(16) . . ? N8 C9 C10 121.9(14) . . ? N2 C3 C4 123.9(15) . . ? C11 C12 C7 115.3(15) . . ? C3 C4 C5 116.8(17) . . ? C11 C10 C9 116.4(17) . . ? C12 C11 C10 124.4(18) . . ? C6 C5 C4 120.9(14) . . ? _diffrn_measured_fraction_theta_max 0.735 _diffrn_reflns_theta_full 37.51 _diffrn_measured_fraction_theta_full 0.735 _refine_diff_density_max 4.639 _refine_diff_density_min -4.096 _refine_diff_density_rms 0.601 _database_code_depnum_ccdc_archive 'CCDC 951477' ####################################################################### # # 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_C:\1_193.CIF _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1_193 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 Br2 N2 Zn' _chemical_formula_weight 381.37 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' Zn Zn 0.2839 1.4301 '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 7.8185(9) _cell_length_b 9.0276(10) _cell_length_c 9.2664(12) _cell_angle_alpha 113.539(6) _cell_angle_beta 95.267(6) _cell_angle_gamma 95.631(5) _cell_volume 590.54(12) _cell_formula_units_Z 2 _cell_measurement_temperature 191(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.145 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 8.812 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2717 _exptl_absorpt_correction_T_max 0.2717 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 191(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8008 _diffrn_reflns_av_R_equivalents 0.1681 _diffrn_reflns_av_sigmaI/netI 0.1132 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 38.05 _reflns_number_total 4698 _reflns_number_gt 2633 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker)' _computing_cell_refinement 'APEX (Bruker)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour,2001;Atwood&Barbour,2003)' _computing_publication_material 'X-Seed (Barbour,2001;Atwood&Barbour,2003)' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4698 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2056 _refine_ls_R_factor_gt 0.1525 _refine_ls_wR_factor_ref 0.4836 _refine_ls_wR_factor_gt 0.4581 _refine_ls_goodness_of_fit_ref 1.589 _refine_ls_restrained_S_all 1.589 _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 Br1 Br 0.96239(18) 0.18056(17) 0.2121(2) 0.0387(5) Uani 1 1 d . . . Zn1 Zn 1.2349(2) 0.28687(18) 0.1794(2) 0.0312(4) Uani 1 1 d . . . Br2 Br 1.4758(2) 0.2159(2) 0.2928(2) 0.0415(5) Uani 1 1 d . . . N8 N 1.2813(15) 0.3006(14) -0.0284(16) 0.031(2) Uani 1 1 d . . . N2 N 1.2109(15) 0.5285(13) 0.2348(16) 0.029(2) Uani 1 1 d . . . C7 C 1.2666(15) 0.4473(16) -0.0334(18) 0.029(2) Uani 1 1 d . . . C1 C 1.2226(16) 0.5731(15) 0.1164(18) 0.030(2) Uani 1 1 d . . . C6 C 1.189(2) 0.7290(16) 0.126(2) 0.039(3) Uani 1 1 d . . . H6 H 1.1855 0.7557 0.0361 0.046 Uiso 1 1 calc R . . C9 C 1.3263(18) 0.1818(17) -0.153(2) 0.034(3) Uani 1 1 d . . . H9 H 1.3377 0.0793 -0.1494 0.040 Uiso 1 1 calc R . . C3 C 1.176(2) 0.6369(15) 0.375(2) 0.035(3) Uani 1 1 d . . . H3 H 1.1690 0.6034 0.4596 0.042 Uiso 1 1 calc R . . C12 C 1.288(2) 0.478(2) -0.170(2) 0.038(3) Uani 1 1 d . . . H12 H 1.2678 0.5776 -0.1768 0.045 Uiso 1 1 calc R . . C4 C 1.149(2) 0.7930(18) 0.401(2) 0.037(3) Uani 1 1 d . . . H4 H 1.1233 0.8659 0.5011 0.044 Uiso 1 1 calc R . . C10 C 1.358(2) 0.207(2) -0.292(2) 0.043(4) Uani 1 1 d . . . H10 H 1.3900 0.1237 -0.3819 0.051 Uiso 1 1 calc R . . C11 C 1.340(2) 0.357(2) -0.289(3) 0.046(4) Uani 1 1 d . . . H11 H 1.3668 0.3767 -0.3780 0.055 Uiso 1 1 calc R . . C5 C 1.160(2) 0.8410(18) 0.276(2) 0.043(4) Uani 1 1 d . . . H5 H 1.1479 0.9502 0.2929 0.052 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 Br1 0.0251(6) 0.0526(8) 0.0561(11) 0.0389(7) 0.0129(7) 0.0058(5) Zn1 0.0241(7) 0.0402(7) 0.0428(11) 0.0300(7) 0.0083(7) 0.0060(5) Br2 0.0262(7) 0.0604(9) 0.0525(11) 0.0372(8) 0.0051(7) 0.0117(5) N8 0.023(5) 0.046(5) 0.028(6) 0.020(5) 0.002(5) 0.002(4) N2 0.025(5) 0.038(5) 0.034(7) 0.024(4) 0.004(5) 0.008(3) C7 0.013(4) 0.048(6) 0.028(7) 0.023(5) -0.010(4) -0.003(4) C1 0.022(5) 0.039(5) 0.031(7) 0.022(5) -0.007(5) -0.001(4) C6 0.041(7) 0.035(6) 0.052(10) 0.030(6) 0.010(7) 0.010(5) C9 0.024(5) 0.043(6) 0.037(8) 0.020(6) 0.005(6) 0.000(4) C3 0.045(8) 0.034(5) 0.033(8) 0.024(5) 0.003(6) 0.005(5) C12 0.036(7) 0.059(8) 0.029(8) 0.030(6) 0.008(6) 0.002(6) C4 0.034(7) 0.045(6) 0.038(9) 0.026(6) -0.004(6) 0.007(5) C10 0.046(9) 0.054(7) 0.031(8) 0.019(6) 0.015(7) 0.006(6) C11 0.037(8) 0.070(9) 0.049(11) 0.041(8) 0.018(8) 0.009(7) C5 0.048(9) 0.041(6) 0.053(11) 0.029(7) 0.013(8) 0.013(6) _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 Zn1 2.3456(18) . ? Zn1 N8 2.041(13) . ? Zn1 N2 2.064(10) . ? Zn1 Br2 2.340(2) . ? N8 C9 1.327(19) . ? N8 C7 1.359(17) . ? N2 C1 1.318(19) . ? N2 C3 1.35(2) . ? C7 C12 1.43(2) . ? C7 C1 1.50(2) . ? C1 C6 1.429(16) . ? C6 C5 1.41(3) . ? C9 C10 1.44(2) . ? C3 C4 1.372(18) . ? C12 C11 1.33(3) . ? C4 C5 1.39(2) . ? C10 C11 1.36(2) . ? 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 N8 Zn1 N2 79.9(5) . . ? N8 Zn1 Br2 110.4(3) . . ? N2 Zn1 Br2 120.9(4) . . ? N8 Zn1 Br1 122.3(4) . . ? N2 Zn1 Br1 102.7(3) . . ? Br2 Zn1 Br1 115.97(8) . . ? C9 N8 C7 119.5(13) . . ? C9 N8 Zn1 125.6(10) . . ? C7 N8 Zn1 114.9(10) . . ? C1 N2 C3 119.3(11) . . ? C1 N2 Zn1 114.7(10) . . ? C3 N2 Zn1 125.9(9) . . ? N8 C7 C12 122.9(14) . . ? N8 C7 C1 114.3(12) . . ? C12 C7 C1 122.8(12) . . ? N2 C1 C6 122.9(14) . . ? N2 C1 C7 116.0(11) . . ? C6 C1 C7 121.0(13) . . ? C5 C6 C1 115.6(14) . . ? N8 C9 C10 120.4(14) . . ? N2 C3 C4 123.2(14) . . ? C11 C12 C7 114.7(15) . . ? C3 C4 C5 117.9(16) . . ? C11 C10 C9 116.9(15) . . ? C12 C11 C10 125.3(17) . . ? C4 C5 C6 120.7(13) . . ? _diffrn_measured_fraction_theta_max 0.729 _diffrn_reflns_theta_full 38.05 _diffrn_measured_fraction_theta_full 0.729 _refine_diff_density_max 4.328 _refine_diff_density_min -4.089 _refine_diff_density_rms 0.556 _database_code_depnum_ccdc_archive 'CCDC 951478' ####################################################################### # # 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_C:\1_213.CIF _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1_213 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 Br2 N2 Zn' _chemical_formula_weight 381.37 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' Zn Zn 0.2839 1.4301 '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 7.8238(11) _cell_length_b 9.0676(12) _cell_length_c 9.2577(14) _cell_angle_alpha 113.055(7) _cell_angle_beta 95.086(7) _cell_angle_gamma 95.526(6) _cell_volume 595.75(15) _cell_formula_units_Z 2 _cell_measurement_temperature 212(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.126 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 8.735 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2740 _exptl_absorpt_correction_T_max 0.2740 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 212(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7863 _diffrn_reflns_av_R_equivalents 0.1561 _diffrn_reflns_av_sigmaI/netI 0.1248 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 37.84 _reflns_number_total 4566 _reflns_number_gt 2501 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker)' _computing_cell_refinement 'APEX (Bruker)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour,2001;Atwood&Barbour,2003)' _computing_publication_material 'X-Seed (Barbour,2001;Atwood&Barbour,2003)' _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^)+(0.1759P)^2^+22.2077P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4566 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2238 _refine_ls_R_factor_gt 0.1545 _refine_ls_wR_factor_ref 0.4520 _refine_ls_wR_factor_gt 0.4051 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 Br1 Br 0.9648(2) 0.1816(2) 0.2154(3) 0.0421(5) Uani 1 1 d . . . Zn1 Zn 1.2364(2) 0.2873(2) 0.1807(3) 0.0321(5) Uani 1 1 d . . . Br2 Br 1.4779(2) 0.2163(3) 0.2921(3) 0.0436(5) Uani 1 1 d . . . N8 N 1.2822(17) 0.2996(18) -0.0273(18) 0.031(3) Uani 1 1 d . . . N2 N 1.2115(18) 0.5254(18) 0.232(2) 0.033(3) Uani 1 1 d . . . C7 C 1.2659(19) 0.444(2) -0.035(2) 0.031(3) Uani 1 1 d . . . C1 C 1.2253(19) 0.571(2) 0.116(2) 0.033(3) Uani 1 1 d . . . C6 C 1.193(3) 0.730(2) 0.125(3) 0.039(4) Uani 1 1 d . . . H6 H 1.1921 0.7555 0.0361 0.046 Uiso 1 1 calc R . . C9 C 1.326(2) 0.177(2) -0.152(3) 0.039(4) Uani 1 1 d . . . H9 H 1.3365 0.0763 -0.1485 0.046 Uiso 1 1 calc R . . C3 C 1.177(3) 0.636(2) 0.373(2) 0.037(4) Uani 1 1 d . . . H3 H 1.1705 0.6044 0.4582 0.045 Uiso 1 1 calc R . . C12 C 1.290(3) 0.475(3) -0.171(3) 0.045(5) Uani 1 1 d . . . H12 H 1.2750 0.5739 -0.1772 0.054 Uiso 1 1 calc R . . C4 C 1.151(2) 0.795(2) 0.397(3) 0.040(4) Uani 1 1 d . . . H4 H 1.1276 0.8681 0.4957 0.048 Uiso 1 1 calc R . . C10 C 1.356(3) 0.207(3) -0.291(2) 0.046(5) Uani 1 1 d . . . H10 H 1.3874 0.1250 -0.3797 0.055 Uiso 1 1 calc R . . C11 C 1.338(3) 0.351(3) -0.291(3) 0.048(5) Uani 1 1 d . . . H11 H 1.3601 0.3674 -0.3817 0.057 Uiso 1 1 calc R . . C5 C 1.162(3) 0.841(3) 0.271(3) 0.045(4) Uani 1 1 d . . . H5 H 1.1482 0.9474 0.2846 0.054 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 Br1 0.0246(7) 0.0590(11) 0.0618(14) 0.0416(10) 0.0183(8) 0.0075(6) Zn1 0.0235(8) 0.0424(10) 0.0443(13) 0.0299(9) 0.0125(8) 0.0083(6) Br2 0.0256(8) 0.0672(12) 0.0526(13) 0.0374(10) 0.0075(8) 0.0145(7) N8 0.025(6) 0.051(8) 0.021(7) 0.020(6) 0.006(5) 0.002(5) N2 0.025(6) 0.046(7) 0.035(8) 0.025(6) 0.005(6) 0.006(5) C7 0.019(6) 0.048(8) 0.034(9) 0.027(7) 0.003(6) -0.001(5) C1 0.018(6) 0.042(8) 0.042(10) 0.023(7) -0.003(6) 0.002(5) C6 0.045(9) 0.037(8) 0.045(12) 0.027(8) 0.011(8) 0.011(6) C9 0.027(7) 0.045(9) 0.045(12) 0.018(8) 0.010(7) 0.005(6) C3 0.043(9) 0.044(8) 0.036(10) 0.027(7) 0.004(8) 0.011(7) C12 0.038(9) 0.079(13) 0.032(11) 0.038(9) 0.009(8) -0.003(8) C4 0.034(8) 0.047(9) 0.047(12) 0.028(8) -0.004(8) 0.007(6) C10 0.037(9) 0.078(14) 0.019(9) 0.012(8) 0.014(8) 0.012(8) C11 0.039(10) 0.079(14) 0.036(12) 0.035(10) 0.014(9) 0.000(8) C5 0.050(11) 0.051(10) 0.040(12) 0.025(8) 0.006(9) 0.008(8) _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 Zn1 2.347(2) . ? Zn1 N8 2.032(14) . ? Zn1 N2 2.054(14) . ? Zn1 Br2 2.336(3) . ? N8 C9 1.35(2) . ? N8 C7 1.36(2) . ? N2 C1 1.30(2) . ? N2 C3 1.37(3) . ? C7 C12 1.42(2) . ? C7 C1 1.51(3) . ? C1 C6 1.45(2) . ? C6 C5 1.39(3) . ? C9 C10 1.44(3) . ? C3 C4 1.41(2) . ? C12 C11 1.34(3) . ? C4 C5 1.39(3) . ? C10 C11 1.33(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N8 Zn1 N2 79.7(6) . . ? N8 Zn1 Br2 109.9(4) . . ? N2 Zn1 Br2 121.3(5) . . ? N8 Zn1 Br1 122.2(4) . . ? N2 Zn1 Br1 102.9(4) . . ? Br2 Zn1 Br1 116.12(10) . . ? C9 N8 C7 120.1(15) . . ? C9 N8 Zn1 124.8(13) . . ? C7 N8 Zn1 115.1(11) . . ? C1 N2 C3 118.2(14) . . ? C1 N2 Zn1 115.8(13) . . ? C3 N2 Zn1 126.0(11) . . ? N8 C7 C12 123.4(18) . . ? N8 C7 C1 113.9(14) . . ? C12 C7 C1 122.7(16) . . ? N2 C1 C6 123.5(17) . . ? N2 C1 C7 115.3(14) . . ? C6 C1 C7 121.1(16) . . ? C5 C6 C1 116.9(17) . . ? N8 C9 C10 117.8(17) . . ? N2 C3 C4 122.9(17) . . ? C11 C12 C7 114(2) . . ? C5 C4 C3 118(2) . . ? C11 C10 C9 119.0(18) . . ? C10 C11 C12 125.3(19) . . ? C4 C5 C6 120.0(18) . . ? _diffrn_measured_fraction_theta_max 0.711 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.820 _refine_diff_density_max 3.000 _refine_diff_density_min -2.794 _refine_diff_density_rms 0.456 _database_code_depnum_ccdc_archive 'CCDC 951479' ####################################################################### # # 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_C:\1_233.CIF _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1_233 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 Br2 N2 Zn' _chemical_formula_weight 381.37 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' Zn Zn 0.2839 1.4301 '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 10.7106(3) _cell_length_b 14.8067(5) _cell_length_c 7.7624(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.299(2) _cell_angle_gamma 90.00 _cell_volume 1218.14(7) _cell_formula_units_Z 4 _cell_measurement_temperature 232(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.080 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 8.544 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2798 _exptl_absorpt_correction_T_max 0.2798 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 232(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8472 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 37.91 _reflns_number_total 3184 _reflns_number_gt 1866 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker)' _computing_cell_refinement 'APEX (Bruker)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour,2001;Atwood&Barbour,2003)' _computing_publication_material 'X-Seed (Barbour,2001;Atwood&Barbour,2003)' _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^)+(0.0424P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3184 _refine_ls_number_parameters 69 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0828 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 Zn1 Zn 0.5000 0.29980(2) 0.2500 0.03113(10) Uani 1 2 d S . . Br1 Br 0.48588(3) 0.214853(17) -0.00619(3) 0.04611(10) Uani 1 1 d . . . N2 N 0.62003(17) 0.40561(12) 0.2238(2) 0.0308(4) Uani 1 1 d . . . C1 C 0.5664(2) 0.48760(14) 0.2338(3) 0.0316(4) Uani 1 1 d . . . C6 C 0.6344(3) 0.56568(18) 0.2130(3) 0.0479(6) Uani 1 1 d . . . H6 H 0.5976 0.6228 0.2224 0.057 Uiso 1 1 calc R . . C3 C 0.7379(2) 0.39968(19) 0.1893(3) 0.0429(5) Uani 1 1 d . . . H3 H 0.7739 0.3422 0.1810 0.052 Uiso 1 1 calc R . . C5 C 0.7558(3) 0.5584(2) 0.1787(4) 0.0609(8) Uani 1 1 d . . . H5 H 0.8027 0.6108 0.1643 0.073 Uiso 1 1 calc R . . C4 C 0.8093(3) 0.4753(2) 0.1651(4) 0.0542(7) Uani 1 1 d . . . H4 H 0.8923 0.4697 0.1401 0.065 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 Zn1 0.0411(2) 0.02421(16) 0.02971(18) 0.000 0.01086(14) 0.000 Br1 0.0690(2) 0.03930(15) 0.03253(14) -0.00839(9) 0.01580(11) -0.00676(10) N2 0.0317(9) 0.0323(9) 0.0285(8) 0.0004(7) 0.0049(6) -0.0013(7) C1 0.0415(12) 0.0285(10) 0.0232(9) 0.0015(7) -0.0008(8) -0.0035(8) C6 0.0596(17) 0.0353(12) 0.0467(14) 0.0067(10) 0.0009(11) -0.0129(11) C3 0.0353(13) 0.0548(15) 0.0399(12) 0.0019(10) 0.0094(10) 0.0018(10) C5 0.064(2) 0.065(2) 0.0522(16) 0.0089(14) 0.0045(13) -0.0340(15) C4 0.0408(15) 0.075(2) 0.0471(15) 0.0035(14) 0.0081(12) -0.0175(14) _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 Zn1 N2 2.0552(18) . ? Zn1 N2 2.0552(18) 2_655 ? Zn1 Br1 2.3393(3) . ? Zn1 Br1 2.3393(3) 2_655 ? N2 C3 1.331(3) . ? N2 C1 1.350(3) . ? C1 C6 1.388(3) . ? C1 C1 1.480(5) 2_655 ? C6 C5 1.369(4) . ? C3 C4 1.384(4) . ? C5 C4 1.368(5) . ? 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 N2 Zn1 N2 80.66(10) . 2_655 ? N2 Zn1 Br1 106.89(5) . . ? N2 Zn1 Br1 121.95(5) 2_655 . ? N2 Zn1 Br1 121.95(5) . 2_655 ? N2 Zn1 Br1 106.89(5) 2_655 2_655 ? Br1 Zn1 Br1 114.954(19) . 2_655 ? C3 N2 C1 119.7(2) . . ? C3 N2 Zn1 126.49(16) . . ? C1 N2 Zn1 113.73(15) . . ? N2 C1 C6 120.5(2) . . ? N2 C1 C1 115.92(12) . 2_655 ? C6 C1 C1 123.59(16) . 2_655 ? C5 C6 C1 119.1(3) . . ? N2 C3 C4 122.2(3) . . ? C4 C5 C6 120.4(3) . . ? C5 C4 C3 118.1(3) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.105 _refine_diff_density_min -1.033 _refine_diff_density_rms 0.110 _database_code_depnum_ccdc_archive 'CCDC 951480' ####################################################################### # # 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_C:\1_253.CIF _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1_253 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 Br2 N2 Zn' _chemical_formula_weight 381.37 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' Zn Zn 0.2839 1.4301 '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 10.7281(5) _cell_length_b 14.8021(7) _cell_length_c 7.7704(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.098(2) _cell_angle_gamma 90.00 _cell_volume 1221.62(9) _cell_formula_units_Z 4 _cell_measurement_temperature 252(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.074 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 8.520 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2806 _exptl_absorpt_correction_T_max 0.2806 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 252(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8497 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 37.90 _reflns_number_total 3191 _reflns_number_gt 1737 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker)' _computing_cell_refinement 'APEX (Bruker)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour,2001;Atwood&Barbour,2003)' _computing_publication_material 'X-Seed (Barbour,2001;Atwood&Barbour,2003)' _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^)+(0.0448P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3191 _refine_ls_number_parameters 69 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0916 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0974 _refine_ls_wR_factor_gt 0.0829 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _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 Zn1 Zn 0.5000 0.29965(2) 0.2500 0.03440(11) Uani 1 2 d S . . Br1 Br 0.48577(3) 0.214854(17) -0.00587(3) 0.05077(11) Uani 1 1 d . . . N2 N 0.61997(17) 0.40558(12) 0.2241(2) 0.0337(4) Uani 1 1 d . . . C1 C 0.5664(2) 0.48745(14) 0.2338(3) 0.0349(4) Uani 1 1 d . . . C6 C 0.6343(3) 0.56555(18) 0.2134(4) 0.0521(6) Uani 1 1 d . . . H6 H 0.5974 0.6226 0.2225 0.063 Uiso 1 1 calc R . . C3 C 0.7378(2) 0.39958(19) 0.1899(3) 0.0473(6) Uani 1 1 d . . . H3 H 0.7738 0.3421 0.1819 0.057 Uiso 1 1 calc R . . C5 C 0.7555(3) 0.5584(2) 0.1797(4) 0.0658(9) Uani 1 1 d . . . H5 H 0.8026 0.6109 0.1662 0.079 Uiso 1 1 calc R . . C4 C 0.8087(3) 0.4753(2) 0.1657(4) 0.0597(7) Uani 1 1 d . . . H4 H 0.8915 0.4698 0.1402 0.072 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 Zn1 0.0452(2) 0.02717(17) 0.03268(19) 0.000 0.01189(15) 0.000 Br1 0.0754(2) 0.04372(16) 0.03579(14) -0.00909(9) 0.01705(12) -0.00729(11) N2 0.0344(10) 0.0359(9) 0.0309(8) 0.0011(7) 0.0052(7) -0.0014(7) C1 0.0462(12) 0.0316(10) 0.0250(9) 0.0015(7) -0.0009(8) -0.0044(8) C6 0.0631(18) 0.0387(13) 0.0528(15) 0.0072(11) 0.0023(12) -0.0135(11) C3 0.0375(13) 0.0602(16) 0.0458(13) 0.0027(11) 0.0108(10) 0.0016(11) C5 0.067(2) 0.070(2) 0.0594(17) 0.0088(15) 0.0060(14) -0.0356(16) C4 0.0452(16) 0.083(2) 0.0519(16) 0.0023(15) 0.0084(12) -0.0189(15) _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 Zn1 N2 2.0563(18) . ? Zn1 N2 2.0563(18) 2_655 ? Zn1 Br1 2.3380(3) . ? Zn1 Br1 2.3380(3) 2_655 ? N2 C3 1.331(3) . ? N2 C1 1.348(3) . ? C1 C6 1.388(3) . ? C1 C1 1.480(5) 2_655 ? C6 C5 1.366(4) . ? C3 C4 1.383(4) . ? C5 C4 1.366(5) . ? 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 N2 Zn1 N2 80.62(10) . 2_655 ? N2 Zn1 Br1 107.04(5) . . ? N2 Zn1 Br1 121.72(5) 2_655 . ? N2 Zn1 Br1 121.72(5) . 2_655 ? N2 Zn1 Br1 107.04(5) 2_655 2_655 ? Br1 Zn1 Br1 115.061(19) . 2_655 ? C3 N2 C1 119.7(2) . . ? C3 N2 Zn1 126.43(16) . . ? C1 N2 Zn1 113.72(15) . . ? N2 C1 C6 120.5(2) . . ? N2 C1 C1 115.95(13) . 2_655 ? C6 C1 C1 123.56(17) . 2_655 ? C5 C6 C1 119.1(3) . . ? N2 C3 C4 122.0(3) . . ? C6 C5 C4 120.3(3) . . ? C5 C4 C3 118.3(3) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.963 _refine_diff_density_min -0.963 _refine_diff_density_rms 0.100 _database_code_depnum_ccdc_archive 'CCDC 951481' ####################################################################### # # 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_C:\1_273.CIF _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 1_273 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 Br2 N2 Zn' _chemical_formula_weight 381.37 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' Zn Zn 0.2839 1.4301 '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 10.7501(5) _cell_length_b 14.7970(8) _cell_length_c 7.7792(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.911(3) _cell_angle_gamma 90.00 _cell_volume 1225.65(11) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.067 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 8.492 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2815 _exptl_absorpt_correction_T_max 0.2815 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8487 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 37.42 _reflns_number_total 3167 _reflns_number_gt 1614 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker)' _computing_cell_refinement 'APEX (Bruker)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour,2001;Atwood&Barbour,2003)' _computing_publication_material 'X-Seed (Barbour,2001;Atwood&Barbour,2003)' _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^)+(0.0472P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3167 _refine_ls_number_parameters 69 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1011 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.1021 _refine_ls_wR_factor_gt 0.0847 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.944 _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 Zn1 Zn 0.5000 0.29951(2) 0.2500 0.03733(12) Uani 1 2 d S . . Br1 Br 0.48573(3) 0.214820(18) -0.00554(3) 0.05521(12) Uani 1 1 d . . . N2 N 0.61974(18) 0.40550(13) 0.2244(2) 0.0368(4) Uani 1 1 d . . . C1 C 0.5661(2) 0.48722(15) 0.2338(3) 0.0379(5) Uani 1 1 d . . . C6 C 0.6338(3) 0.56555(19) 0.2137(4) 0.0554(7) Uani 1 1 d . . . H6 H 0.5973 0.6220 0.2228 0.067 Uiso 1 1 calc R . . C3 C 0.7373(2) 0.3994(2) 0.1904(4) 0.0506(6) Uani 1 1 d . . . H3 H 0.7728 0.3426 0.1821 0.061 Uiso 1 1 calc R . . C5 C 0.7553(3) 0.5581(3) 0.1803(5) 0.0721(10) Uani 1 1 d . . . H5 H 0.8018 0.6100 0.1667 0.086 Uiso 1 1 calc R . . C4 C 0.8083(3) 0.4752(3) 0.1671(4) 0.0647(8) Uani 1 1 d . . . H4 H 0.8903 0.4698 0.1429 0.078 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 Zn1 0.0490(3) 0.02948(18) 0.0355(2) 0.000 0.01270(16) 0.000 Br1 0.0818(3) 0.04759(17) 0.03903(16) -0.00976(10) 0.01821(13) -0.00782(12) N2 0.0370(10) 0.0393(10) 0.0344(9) 0.0011(7) 0.0064(7) -0.0021(8) C1 0.0496(13) 0.0343(11) 0.0282(10) 0.0011(8) -0.0005(9) -0.0044(9) C6 0.0644(19) 0.0427(14) 0.0568(16) 0.0083(12) 0.0002(13) -0.0137(12) C3 0.0404(14) 0.0630(17) 0.0500(14) 0.0021(12) 0.0112(11) 0.0014(12) C5 0.074(2) 0.077(2) 0.0649(19) 0.0105(17) 0.0055(16) -0.0398(18) C4 0.0490(17) 0.088(2) 0.0575(18) 0.0049(17) 0.0099(13) -0.0198(16) _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 Zn1 N2 2.0558(19) . ? Zn1 N2 2.0558(19) 2_655 ? Zn1 Br1 2.3371(3) . ? Zn1 Br1 2.3371(3) 2_655 ? N2 C3 1.330(3) . ? N2 C1 1.346(3) . ? C1 C6 1.389(3) . ? C1 C1 1.477(5) 2_655 ? C6 C5 1.371(5) . ? C3 C4 1.383(4) . ? C5 C4 1.362(5) . ? 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 N2 Zn1 N2 80.57(11) . 2_655 ? N2 Zn1 Br1 107.18(5) . . ? N2 Zn1 Br1 121.51(5) 2_655 . ? N2 Zn1 Br1 121.51(5) . 2_655 ? N2 Zn1 Br1 107.18(5) 2_655 2_655 ? Br1 Zn1 Br1 115.15(2) . 2_655 ? C3 N2 C1 119.9(2) . . ? C3 N2 Zn1 126.35(17) . . ? C1 N2 Zn1 113.66(16) . . ? N2 C1 C6 120.6(3) . . ? N2 C1 C1 116.02(13) . 2_655 ? C6 C1 C1 123.39(17) . 2_655 ? C5 C6 C1 118.8(3) . . ? N2 C3 C4 121.9(3) . . ? C4 C5 C6 120.4(3) . . ? C5 C4 C3 118.5(3) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.961 _refine_diff_density_min -1.047 _refine_diff_density_rms 0.097 _database_code_depnum_ccdc_archive 'CCDC 951482'