data_rd23 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 Br N2 O S2' _chemical_formula_weight 343.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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)/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 16.084(3) _cell_length_b 4.5450(9) _cell_length_c 19.622(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.97(3) _cell_angle_gamma 90.00 _cell_volume 1420.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2953 _cell_measurement_theta_min 4.4 _cell_measurement_theta_max 25.0 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 3.176 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5287 _exptl_absorpt_correction_T_max 0.7018 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1 _diffrn_reflns_number 7550 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 25.69 _reflns_number_total 2489 _reflns_number_gt 1935 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT+' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.6000P] 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 2489 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1181 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _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 0.84869(3) 1.11805(14) 0.48029(3) 0.0914(3) Uani 1 1 d . . . S1 S 0.33753(7) 0.0744(2) 0.33627(6) 0.0540(3) Uani 1 1 d . . . S2 S 0.55932(7) 0.9241(3) 0.19206(6) 0.0568(3) Uani 1 1 d . . . O1 O 0.38816(19) -0.0399(6) 0.40078(16) 0.0629(8) Uani 1 1 d . . . N1 N 0.3799(2) 0.3995(7) 0.23487(18) 0.0520(9) Uani 1 1 d . . . N2 N 0.4289(2) 0.5841(7) 0.20318(17) 0.0496(8) Uani 1 1 d . . . C1 C 0.2656(2) 0.3369(9) 0.3628(2) 0.0583(12) Uani 1 1 d . . . H1A H 0.2232 0.2362 0.3837 0.070 Uiso 1 1 calc R . . H1B H 0.2398 0.4453 0.3235 0.070 Uiso 1 1 calc R . . H1C H 0.2954 0.4701 0.3955 0.070 Uiso 1 1 calc R . . C2 C 0.4053(2) 0.3305(8) 0.3003(2) 0.0463(10) Uani 1 1 d . . . C3 C 0.4793(2) 0.4321(8) 0.3385(2) 0.0443(9) Uani 1 1 d . . . H3A H 0.4935 0.3782 0.3844 0.053 Uiso 1 1 calc R . . C4 C 0.5307(2) 0.6121(8) 0.30732(19) 0.0411(9) Uani 1 1 d . . . C5 C 0.5010(2) 0.6848(8) 0.2378(2) 0.0413(9) Uani 1 1 d . . . C6 C 0.4884(3) 0.9858(11) 0.1132(2) 0.0657(12) Uani 1 1 d . . . H6A H 0.5130 1.1247 0.0850 0.079 Uiso 1 1 calc R . . H6B H 0.4362 1.0620 0.1240 0.079 Uiso 1 1 calc R . . H6C H 0.4786 0.8033 0.0888 0.079 Uiso 1 1 calc R . . C7 C 0.6087(2) 0.7343(8) 0.34719(19) 0.0427(9) Uani 1 1 d . . . C8 C 0.6860(3) 0.7279(10) 0.3229(2) 0.0563(11) Uani 1 1 d . . . H8A H 0.6900 0.6472 0.2799 0.068 Uiso 1 1 calc R . . C9 C 0.7577(3) 0.8415(10) 0.3625(2) 0.0602(12) Uani 1 1 d . . . H9A H 0.8094 0.8356 0.3463 0.072 Uiso 1 1 calc R . . C10 C 0.7510(3) 0.9616(10) 0.4255(2) 0.0547(11) Uani 1 1 d . . . C11 C 0.6759(3) 0.9697(10) 0.4514(2) 0.0569(11) Uani 1 1 d . . . H11A H 0.6724 1.0511 0.4944 0.068 Uiso 1 1 calc R . . C12 C 0.6052(2) 0.8532(9) 0.4117(2) 0.0498(10) Uani 1 1 d . . . H12A H 0.5542 0.8552 0.4290 0.060 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 0.0661(4) 0.1278(6) 0.0735(4) 0.0003(3) -0.0147(3) -0.0318(3) S1 0.0589(7) 0.0446(6) 0.0607(7) -0.0043(5) 0.0160(5) -0.0098(5) S2 0.0512(6) 0.0685(8) 0.0506(7) 0.0113(6) 0.0070(5) -0.0047(5) O1 0.0632(19) 0.0570(18) 0.072(2) 0.0159(16) 0.0221(16) 0.0092(15) N1 0.0463(19) 0.057(2) 0.053(2) -0.0033(18) 0.0072(16) -0.0027(16) N2 0.0453(19) 0.058(2) 0.046(2) -0.0004(16) 0.0049(16) -0.0026(16) C1 0.044(2) 0.063(3) 0.069(3) 0.004(2) 0.013(2) -0.003(2) C2 0.051(2) 0.041(2) 0.049(3) -0.0031(18) 0.014(2) -0.0022(18) C3 0.047(2) 0.045(2) 0.040(2) -0.0027(18) 0.0059(18) 0.0049(18) C4 0.040(2) 0.043(2) 0.041(2) -0.0057(17) 0.0073(17) 0.0044(17) C5 0.042(2) 0.039(2) 0.045(2) -0.0017(17) 0.0109(18) 0.0055(16) C6 0.069(3) 0.078(3) 0.050(3) 0.010(2) 0.006(2) 0.006(2) C7 0.043(2) 0.046(2) 0.040(2) 0.0067(18) 0.0073(18) 0.0059(17) C8 0.047(2) 0.076(3) 0.045(3) -0.010(2) 0.006(2) 0.004(2) C9 0.036(2) 0.087(3) 0.058(3) 0.001(2) 0.009(2) 0.005(2) C10 0.049(2) 0.065(3) 0.046(3) 0.003(2) -0.007(2) -0.008(2) C11 0.056(3) 0.070(3) 0.044(2) -0.005(2) 0.007(2) 0.001(2) C12 0.041(2) 0.063(3) 0.046(2) -0.0018(19) 0.0100(19) 0.0020(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 C10 1.914(4) . ? S1 O1 1.500(3) . ? S1 C1 1.789(4) . ? S1 C2 1.804(4) . ? S2 C5 1.760(4) . ? S2 C6 1.812(4) . ? N1 C2 1.330(5) . ? N1 N2 1.359(4) . ? N2 C5 1.341(5) . ? C2 C3 1.395(5) . ? C3 C4 1.366(5) . ? C4 C5 1.421(5) . ? C4 C7 1.491(5) . ? C7 C12 1.385(5) . ? C7 C8 1.392(5) . ? C8 C9 1.397(5) . ? C9 C10 1.369(6) . ? C10 C11 1.374(6) . ? C11 C12 1.390(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 O1 S1 C1 106.4(2) . . ? O1 S1 C2 105.47(19) . . ? C1 S1 C2 97.68(19) . . ? C5 S2 C6 102.4(2) . . ? C2 N1 N2 117.9(3) . . ? C5 N2 N1 119.7(3) . . ? N1 C2 C3 124.4(4) . . ? N1 C2 S1 114.1(3) . . ? C3 C2 S1 121.4(3) . . ? C4 C3 C2 118.8(4) . . ? C3 C4 C5 115.2(3) . . ? C3 C4 C7 120.3(3) . . ? C5 C4 C7 124.3(3) . . ? N2 C5 C4 123.9(4) . . ? N2 C5 S2 116.0(3) . . ? C4 C5 S2 120.1(3) . . ? C12 C7 C8 118.2(4) . . ? C12 C7 C4 119.1(3) . . ? C8 C7 C4 122.7(4) . . ? C7 C8 C9 120.6(4) . . ? C10 C9 C8 119.1(4) . . ? C9 C10 C11 121.9(4) . . ? C9 C10 Br1 119.5(3) . . ? C11 C10 Br1 118.6(3) . . ? C10 C11 C12 118.4(4) . . ? C7 C12 C11 121.8(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 C2 N1 N2 C5 1.4(5) . . . . ? N2 N1 C2 C3 -0.8(6) . . . . ? N2 N1 C2 S1 -177.9(3) . . . . ? O1 S1 C2 N1 164.0(3) . . . . ? C1 S1 C2 N1 -86.5(3) . . . . ? O1 S1 C2 C3 -13.2(4) . . . . ? C1 S1 C2 C3 96.2(3) . . . . ? N1 C2 C3 C4 -0.8(6) . . . . ? S1 C2 C3 C4 176.2(3) . . . . ? C2 C3 C4 C5 1.6(5) . . . . ? C2 C3 C4 C7 177.7(3) . . . . ? N1 N2 C5 C4 -0.4(5) . . . . ? N1 N2 C5 S2 -179.6(3) . . . . ? C3 C4 C5 N2 -1.1(5) . . . . ? C7 C4 C5 N2 -176.9(3) . . . . ? C3 C4 C5 S2 178.1(3) . . . . ? C7 C4 C5 S2 2.2(5) . . . . ? C6 S2 C5 N2 7.4(3) . . . . ? C6 S2 C5 C4 -171.8(3) . . . . ? C3 C4 C7 C12 -45.8(5) . . . . ? C5 C4 C7 C12 129.8(4) . . . . ? C3 C4 C7 C8 132.6(4) . . . . ? C5 C4 C7 C8 -51.7(6) . . . . ? C12 C7 C8 C9 -0.7(6) . . . . ? C4 C7 C8 C9 -179.1(4) . . . . ? C7 C8 C9 C10 -0.5(7) . . . . ? C8 C9 C10 C11 1.0(7) . . . . ? C8 C9 C10 Br1 -180.0(3) . . . . ? C9 C10 C11 C12 -0.3(7) . . . . ? Br1 C10 C11 C12 -179.4(3) . . . . ? C8 C7 C12 C11 1.3(6) . . . . ? C4 C7 C12 C11 179.8(4) . . . . ? C10 C11 C12 C7 -0.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 25.69 _diffrn_measured_fraction_theta_full 0.915 _refine_diff_density_max 0.476 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.067