data_z _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 Br N2 S' _chemical_formula_weight 282.18 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' 'S' 'S' 0.1246 0.1234 '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 7.6870(12) _cell_length_b 5.6405(9) _cell_length_c 26.624(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.533(2) _cell_angle_gamma 90.00 _cell_volume 1144.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2079 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 24.58 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.638 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 3.741 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3543 _exptl_absorpt_correction_T_max 0.6623 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex II CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6000 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2009 _reflns_number_gt 1617 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0290P)^2^+0.7930P] 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 2009 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0768 _refine_ls_wR_factor_gt 0.0719 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.15775(5) 0.67880(8) 0.367687(14) 0.06739(17) Uani 1 1 d . . . S1 S 0.20789(11) 0.09797(15) 0.00429(3) 0.0493(2) Uani 1 1 d . . . N1 N 0.3454(4) 0.6862(4) 0.11836(10) 0.0461(6) Uani 1 1 d . . . N2 N 0.3817(4) 0.5955(4) 0.07536(10) 0.0473(7) Uani 1 1 d . . . N3 N 0.3832(3) 0.3577(4) 0.08087(9) 0.0368(6) Uani 1 1 d . . . C1 C 0.3331(4) 0.3872(5) 0.24117(11) 0.0388(7) Uani 1 1 d . . . H1A H 0.3916 0.2498 0.2337 0.047 Uiso 1 1 calc R . . C2 C 0.2980(4) 0.4236(5) 0.29009(11) 0.0439(7) Uani 1 1 d . . . H2A H 0.3324 0.3129 0.3153 0.053 Uiso 1 1 calc R . . C3 C 0.2104(4) 0.6285(5) 0.30083(11) 0.0403(7) Uani 1 1 d . . . C4 C 0.1613(4) 0.7944(5) 0.26372(13) 0.0434(7) Uani 1 1 d . . . H4A H 0.1043 0.9325 0.2714 0.052 Uiso 1 1 calc R . . C5 C 0.1972(4) 0.7543(5) 0.21523(12) 0.0409(7) Uani 1 1 d . . . H5A H 0.1629 0.8662 0.1902 0.049 Uiso 1 1 calc R . . C6 C 0.2838(4) 0.5500(4) 0.20255(11) 0.0340(6) Uani 1 1 d . . . C7 C 0.3239(4) 0.5078(5) 0.15121(11) 0.0341(6) Uani 1 1 d . . . C8 C 0.3486(4) 0.2982(5) 0.12712(11) 0.0381(7) Uani 1 1 d . . . H8A H 0.3425 0.1460 0.1402 0.046 Uiso 1 1 calc R . . C9 C 0.4097(4) 0.1998(5) 0.03916(12) 0.0429(7) Uani 1 1 d . . . H9A H 0.4778 0.0638 0.0526 0.051 Uiso 1 1 calc R . . H9B H 0.4771 0.2825 0.0162 0.051 Uiso 1 1 calc R . . C10 C 0.1549(5) 0.3444(6) -0.03781(15) 0.0673(10) Uani 1 1 d . . . H10B H 0.0469 0.3126 -0.0592 0.101 Uiso 1 1 calc R . . H10C H 0.2473 0.3669 -0.0583 0.101 Uiso 1 1 calc R . . H10D H 0.1421 0.4851 -0.0183 0.101 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 0.0701(3) 0.0888(3) 0.0441(2) -0.01670(19) 0.01035(18) -0.0020(2) S1 0.0530(5) 0.0480(4) 0.0466(5) -0.0039(4) 0.0051(4) -0.0081(4) N1 0.0641(18) 0.0294(13) 0.0463(16) 0.0029(11) 0.0130(13) -0.0020(12) N2 0.0650(18) 0.0348(13) 0.0435(16) 0.0027(12) 0.0122(13) -0.0047(12) N3 0.0408(14) 0.0299(12) 0.0408(14) -0.0011(10) 0.0100(11) -0.0022(10) C1 0.0442(17) 0.0298(14) 0.0417(17) 0.0003(13) 0.0030(14) 0.0066(13) C2 0.0467(18) 0.0433(17) 0.0394(18) 0.0069(14) -0.0026(14) 0.0037(15) C3 0.0366(17) 0.0468(18) 0.0372(16) -0.0088(14) 0.0035(13) -0.0049(13) C4 0.0411(17) 0.0309(15) 0.058(2) -0.0092(14) 0.0072(15) 0.0029(13) C5 0.0445(18) 0.0279(14) 0.050(2) 0.0035(13) 0.0059(15) 0.0032(13) C6 0.0313(15) 0.0253(14) 0.0447(17) -0.0027(12) 0.0022(13) -0.0031(11) C7 0.0303(15) 0.0272(14) 0.0443(16) 0.0013(12) 0.0035(13) -0.0022(11) C8 0.0461(17) 0.0287(14) 0.0406(17) 0.0025(12) 0.0097(14) -0.0012(13) C9 0.0436(18) 0.0425(16) 0.0442(18) -0.0028(14) 0.0114(14) 0.0009(14) C10 0.070(3) 0.068(2) 0.062(2) 0.0062(19) 0.001(2) 0.0104(19) _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 C3 1.898(3) . ? S1 C9 1.795(3) . ? S1 C10 1.798(4) . ? N1 N2 1.317(3) . ? N1 C7 1.357(4) . ? N2 N3 1.349(3) . ? N3 C8 1.336(4) . ? N3 C9 1.459(4) . ? C1 C2 1.380(4) . ? C1 C6 1.394(4) . ? C1 H1A 0.9300 . ? C2 C3 1.386(4) . ? C2 H2A 0.9300 . ? C3 C4 1.377(4) . ? C4 C5 1.374(4) . ? C4 H4A 0.9300 . ? C5 C6 1.394(4) . ? C5 H5A 0.9300 . ? C6 C7 1.460(4) . ? C7 C8 1.370(4) . ? C8 H8A 0.9300 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C10 H10D 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 S1 C10 100.66(17) . . ? N2 N1 C7 109.3(2) . . ? N1 N2 N3 106.9(2) . . ? C8 N3 N2 110.5(2) . . ? C8 N3 C9 127.8(2) . . ? N2 N3 C9 121.6(2) . . ? C2 C1 C6 122.0(3) . . ? C2 C1 H1A 119.0 . . ? C6 C1 H1A 119.0 . . ? C1 C2 C3 118.6(3) . . ? C1 C2 H2A 120.7 . . ? C3 C2 H2A 120.7 . . ? C4 C3 C2 120.9(3) . . ? C4 C3 Br1 119.9(2) . . ? C2 C3 Br1 119.2(2) . . ? C5 C4 C3 119.5(3) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? C4 C5 C6 121.7(3) . . ? C4 C5 H5A 119.2 . . ? C6 C5 H5A 119.2 . . ? C1 C6 C5 117.3(3) . . ? C1 C6 C7 120.9(2) . . ? C5 C6 C7 121.8(3) . . ? N1 C7 C8 107.6(3) . . ? N1 C7 C6 122.7(2) . . ? C8 C7 C6 129.7(2) . . ? N3 C8 C7 105.7(2) . . ? N3 C8 H8A 127.2 . . ? C7 C8 H8A 127.2 . . ? N3 C9 S1 113.0(2) . . ? N3 C9 H9A 109.0 . . ? S1 C9 H9A 109.0 . . ? N3 C9 H9B 109.0 . . ? S1 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? S1 C10 H10B 109.5 . . ? S1 C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? S1 C10 H10D 109.5 . . ? H10B C10 H10D 109.5 . . ? H10C C10 H10D 109.5 . . ? 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 C7 N1 N2 N3 0.1(3) . . . . ? N1 N2 N3 C8 -0.2(3) . . . . ? N1 N2 N3 C9 176.6(3) . . . . ? C6 C1 C2 C3 0.2(4) . . . . ? C1 C2 C3 C4 -0.9(4) . . . . ? C1 C2 C3 Br1 179.0(2) . . . . ? C2 C3 C4 C5 1.0(4) . . . . ? Br1 C3 C4 C5 -178.8(2) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C2 C1 C6 C5 0.3(4) . . . . ? C2 C1 C6 C7 179.5(3) . . . . ? C4 C5 C6 C1 -0.1(4) . . . . ? C4 C5 C6 C7 -179.3(3) . . . . ? N2 N1 C7 C8 0.1(3) . . . . ? N2 N1 C7 C6 179.5(2) . . . . ? C1 C6 C7 N1 -152.8(3) . . . . ? C5 C6 C7 N1 26.4(4) . . . . ? C1 C6 C7 C8 26.4(5) . . . . ? C5 C6 C7 C8 -154.3(3) . . . . ? N2 N3 C8 C7 0.2(3) . . . . ? C9 N3 C8 C7 -176.2(3) . . . . ? N1 C7 C8 N3 -0.2(3) . . . . ? C6 C7 C8 N3 -179.5(3) . . . . ? C8 N3 C9 S1 81.6(3) . . . . ? N2 N3 C9 S1 -94.6(3) . . . . ? C10 S1 C9 N3 82.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.417 _refine_diff_density_min -0.470 _refine_diff_density_rms 0.053