data_andy01b _audit_update_record ; 2011-04-18 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H13 Br S' _chemical_formula_weight 305.22 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' '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 'C 2/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 30.840(3) _cell_length_b 7.1498(7) _cell_length_c 5.8545(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.531(3) _cell_angle_gamma 90.00 _cell_volume 1282.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3095 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 29.06 _exptl_crystal_description 'hexagonal plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_min 0.097 _exptl_crystal_size_mid 0.234 _exptl_crystal_size_max 0.531 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 3.341 ############################################################################## # # # NOTE on absorbtion correction with SADABS: # # # # (Semi)empirical correction methods for absorption correction are more of # # a problem in that they often specify only a relative correction range # # [ Tmin(emp) & Tmax(emp)]. # # # # Acta Cryst. procedures call in such cases for the multiplication of both # # empirical values with Tmax(expected). # # # # THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW! (George # # and Ton are agruing this point!) # # # ############################################################################## _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2007)' _exptl_absorpt_correction_T_min 0.2700 _exptl_absorpt_correction_T_max 0.7376 _exptl_special_details ? _diffrn_ambient_temperature 100(2) # APEX 2 parameters _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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6560 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 29.12 _reflns_number_total 1685 _reflns_number_gt 1478 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2.1-0 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 v2.1-0 (Bruker, 2006)' _computing_data_reduction ; Bruker SAINT v7.34A (Bruker, 2005), Bruker XPREP v2005/2 (Bruker, 2004) ; _computing_structure_solution 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_structure_refinement 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_molecular_graphics 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _computing_publication_material 'Bruker SHELXTL v6.12 (Bruker, 2000b)' _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^)+(0.1109P)^2^+4.0101P] 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 1685 _refine_ls_number_parameters 103 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1763 _refine_ls_wR_factor_gt 0.1699 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.001 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 0.44541(3) 0.79702(18) 0.0949(2) 0.0381(3) Uani 0.50 1 d P A 1 S1 S 0.44409(8) 0.7881(6) 0.0453(5) 0.0728(15) Uani 0.50 1 d PD A 2 C1A C 0.48101(9) 0.7306(4) -0.1459(6) 0.069(3) Uani 0.50 1 d PD . 2 H1AA H 0.51073(14) 0.7452(12) -0.079(2) 0.103 Uiso 0.50 1 d PD B 2 H1AB H 0.4762(4) 0.6037(5) -0.196(2) 0.103 Uiso 0.50 1 d PD C 2 H1AC H 0.4753(5) 0.8135(13) -0.2746(17) 0.103 Uiso 0.50 1 d PD D 2 C1 C 0.39161(8) 0.7685(4) -0.0987(5) 0.0265(5) Uani 1 1 d D . . C2 C 0.35386(10) 0.8338(4) -0.0090(5) 0.0285(6) Uani 1 1 d . A . H2A H 0.3560 0.8900 0.1389 0.034 Uiso 1 1 calc R . . C3 C 0.31360(10) 0.8150(4) -0.1387(5) 0.0301(6) Uani 1 1 d . . . H3A H 0.2881 0.8591 -0.0786 0.036 Uiso 1 1 calc R A . C4 C 0.30978(11) 0.7318(4) -0.3583(5) 0.0326(6) Uani 1 1 d . A . C5 C 0.34741(11) 0.6667(4) -0.4391(5) 0.0330(6) Uani 1 1 d . . . H5A H 0.3454 0.6074 -0.5852 0.040 Uiso 1 1 calc R A . C6 C 0.38791(11) 0.6856(4) -0.3137(5) 0.0309(6) Uani 1 1 d . A . H6A H 0.4133 0.6416 -0.3751 0.037 Uiso 1 1 calc R . . C7 C 0.26896(12) 0.7100(4) -0.5160(5) 0.0327(6) Uani 1 1 d . . . H7A H 0.2681(13) 0.629(6) -0.677(7) 0.039 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0301(4) 0.0495(5) 0.0331(4) -0.0066(3) -0.0034(3) -0.0008(3) S1 0.092(2) 0.0618(19) 0.0525(18) 0.0206(13) -0.0430(15) -0.0405(16) C1A 0.031(4) 0.058(5) 0.112(9) -0.004(5) -0.011(4) 0.001(3) C1 0.0272(12) 0.0261(12) 0.0255(12) 0.0011(10) 0.0000(10) 0.0001(10) C2 0.0388(14) 0.0220(11) 0.0259(12) -0.0004(9) 0.0088(10) 0.0013(10) C3 0.0312(13) 0.0230(12) 0.0375(15) 0.0062(10) 0.0092(11) 0.0025(9) C4 0.0355(15) 0.0243(12) 0.0363(15) 0.0100(11) -0.0029(12) -0.0041(11) C5 0.0486(17) 0.0273(13) 0.0225(12) -0.0002(10) 0.0008(11) -0.0073(12) C6 0.0359(14) 0.0286(13) 0.0293(13) -0.0013(10) 0.0080(11) -0.0007(10) C7 0.0437(17) 0.0276(14) 0.0268(13) 0.0002(10) 0.0041(12) -0.0016(11) _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 C1 1.911(3) . ? S1 C1A 1.7343(19) . ? S1 C1 1.7433(19) . ? C1A C1A 1.784(6) 2_654 ? C1A H1AA 0.9599(10) . ? C1A H1AB 0.9599(10) . ? C1A H1AC 0.9599(10) . ? C1 C6 1.384(4) . ? C1 C2 1.410(4) . ? C2 C3 1.386(4) . ? C2 H2A 0.9500 . ? C3 C4 1.410(4) . ? C3 H3A 0.9500 . ? C4 C5 1.383(5) . ? C4 C7 1.482(4) . ? C5 C6 1.382(5) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C7 1.334(7) 7_564 ? C7 H7A 1.10(4) . ? 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 C1A S1 C1 108.1(2) . . ? S1 C1A C1A 166.20(17) . 2_654 ? S1 C1A H1AA 112.2(8) . . ? C1A C1A H1AA 66.9(8) 2_654 . ? S1 C1A H1AB 109.4(9) . . ? C1A C1A H1AB 83.1(9) 2_654 . ? H1AA C1A H1AB 109.5(2) . . ? S1 C1A H1AC 106.5(10) . . ? C1A C1A H1AC 62.6(10) 2_654 . ? H1AA C1A H1AC 109.5(2) . . ? H1AB C1A H1AC 109.5(2) . . ? C6 C1 C2 119.6(2) . . ? C6 C1 S1 116.7(2) . . ? C2 C1 S1 123.6(2) . . ? C6 C1 Br1 124.1(2) . . ? C2 C1 Br1 116.2(2) . . ? S1 C1 Br1 7.66(11) . . ? C3 C2 C1 119.3(3) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C2 C3 C4 121.1(3) . . ? C2 C3 H3A 119.4 . . ? C4 C3 H3A 119.4 . . ? C5 C4 C3 117.9(3) . . ? C5 C4 C7 116.0(3) . . ? C3 C4 C7 126.1(3) . . ? C4 C5 C6 121.9(3) . . ? C4 C5 H5A 119.0 . . ? C6 C5 H5A 119.0 . . ? C5 C6 C1 120.1(3) . . ? C5 C6 H6A 120.0 . . ? C1 C6 H6A 120.0 . . ? C7 C7 C4 124.3(4) 7_564 . ? C7 C7 H7A 114(2) 7_564 . ? C4 C7 H7A 122(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 S1 C1A C1A 93.4(13) . . . 2_654 ? C1A S1 C1 C6 10.1(4) . . . . ? C1A S1 C1 C2 -169.2(3) . . . . ? C1A S1 C1 Br1 175.7(14) . . . . ? C6 C1 C2 C3 -0.5(4) . . . . ? S1 C1 C2 C3 178.7(3) . . . . ? Br1 C1 C2 C3 -179.1(2) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C2 C3 C4 C5 0.9(4) . . . . ? C2 C3 C4 C7 -177.7(3) . . . . ? C3 C4 C5 C6 -1.6(4) . . . . ? C7 C4 C5 C6 177.2(3) . . . . ? C4 C5 C6 C1 1.2(4) . . . . ? C2 C1 C6 C5 -0.1(4) . . . . ? S1 C1 C6 C5 -179.4(3) . . . . ? Br1 C1 C6 C5 178.3(2) . . . . ? C5 C4 C7 C7 -168.9(4) . . . 7_564 ? C3 C4 C7 C7 9.8(6) . . . 7_564 ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.690 _refine_diff_density_min -0.908 _refine_diff_density_rms 0.107