# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_a _database_code_depnum_ccdc_archive 'CCDC 902936' #TrackingRef 'A.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H11 Br S' _chemical_formula_sum 'C14 H11 Br S' _chemical_formula_weight 291.20 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.0206(4) _cell_length_b 10.2488(7) _cell_length_c 20.3688(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1256.83(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2954 _cell_measurement_theta_min 2.00 _cell_measurement_theta_max 24.98 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.403 _exptl_crystal_size_mid 0.204 _exptl_crystal_size_min 0.057 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 3.405 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.924 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 APEX-II area-detector diffractometer' _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_% ? _diffrn_reflns_number 8909 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2206 _reflns_number_gt 1546 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEXII (Bruker, 2006)' _computing_cell_refinement 'SAINT (Bruker, 2006)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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^)+(0.0351P)^2^+0.0358P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.014(15) _refine_ls_number_reflns 2206 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0815 _refine_ls_wR_factor_gt 0.0740 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 0.51960(8) 0.33829(4) 0.52981(2) 0.06512(19) Uani 1 1 d . . . S2 S 0.1114(2) 0.46911(12) 0.59242(7) 0.0730(4) Uani 1 1 d . . . C1 C 0.3780(11) 0.9972(5) 0.6156(2) 0.0700(16) Uani 1 1 d . . . H1A H 0.3572 1.0839 0.6277 0.084 Uiso 1 1 calc R . . C2 C 0.2141(10) 0.9076(5) 0.6262(3) 0.0764(17) Uani 1 1 d . . . H2A H 0.0817 0.9331 0.6459 0.092 Uiso 1 1 calc R . . C3 C 0.2443(8) 0.7790(5) 0.6078(2) 0.0637(14) Uani 1 1 d . . . H3A H 0.1303 0.7191 0.6142 0.076 Uiso 1 1 calc R . . C4 C 0.4422(7) 0.7381(4) 0.57971(18) 0.0438(11) Uani 1 1 d . . . C5 C 0.6065(8) 0.8312(5) 0.5708(2) 0.0617(13) Uani 1 1 d . . . H5A H 0.7427 0.8061 0.5534 0.074 Uiso 1 1 calc R . . C6 C 0.5729(10) 0.9587(5) 0.5870(2) 0.0740(17) Uani 1 1 d . . . H6A H 0.6833 1.0200 0.5786 0.089 Uiso 1 1 calc R . . C7 C 0.4951(8) 0.6030(4) 0.55945(17) 0.0432(10) Uani 1 1 d . . . H7A H 0.6321 0.5944 0.5388 0.052 Uiso 1 1 calc R . . C8 C 0.3841(8) 0.4919(4) 0.5652(2) 0.0519(12) Uani 1 1 d . . . C9 C 0.1469(8) 0.3584(4) 0.6589(2) 0.0517(11) Uani 1 1 d . . . C10 C -0.0244(9) 0.2718(4) 0.6703(2) 0.0661(13) Uani 1 1 d . . . H10A H -0.1473 0.2713 0.6426 0.079 Uiso 1 1 calc R . . C11 C -0.0146(11) 0.1856(5) 0.7226(3) 0.0833(16) Uani 1 1 d . . . H11A H -0.1306 0.1280 0.7309 0.100 Uiso 1 1 calc R . . C12 C 0.1728(12) 0.1874(6) 0.7621(3) 0.0881(19) Uani 1 1 d . . . H12A H 0.1835 0.1298 0.7973 0.106 Uiso 1 1 calc R . . C13 C 0.3430(11) 0.2737(6) 0.7499(3) 0.0856(18) Uani 1 1 d . . . H13A H 0.4688 0.2735 0.7764 0.103 Uiso 1 1 calc R . . C14 C 0.3272(9) 0.3597(5) 0.6987(2) 0.0698(15) Uani 1 1 d . . . H14A H 0.4408 0.4194 0.6912 0.084 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 0.0679(3) 0.0481(3) 0.0794(3) -0.0082(2) -0.0040(4) 0.0072(3) S2 0.0451(8) 0.0601(8) 0.1137(11) 0.0229(8) 0.0035(8) 0.0004(7) C1 0.100(5) 0.042(3) 0.069(4) -0.011(2) 0.004(3) 0.002(3) C2 0.069(4) 0.058(4) 0.103(4) -0.021(3) 0.006(3) 0.008(3) C3 0.050(3) 0.053(3) 0.088(4) -0.004(3) -0.001(3) -0.006(3) C4 0.044(3) 0.046(3) 0.041(2) -0.0003(19) 0.004(2) -0.003(2) C5 0.065(3) 0.057(3) 0.063(3) 0.000(3) 0.019(2) -0.013(3) C6 0.108(5) 0.049(3) 0.066(3) -0.005(3) 0.019(3) -0.019(3) C7 0.039(3) 0.050(2) 0.041(2) -0.0021(18) -0.002(2) -0.002(3) C8 0.047(3) 0.048(3) 0.060(3) 0.003(2) 0.000(2) 0.002(2) C9 0.046(3) 0.051(3) 0.058(3) -0.002(2) 0.007(3) 0.002(2) C10 0.059(3) 0.069(3) 0.070(3) 0.001(3) 0.005(3) 0.003(3) C11 0.083(4) 0.084(4) 0.084(4) 0.012(3) 0.022(4) -0.006(5) C12 0.108(5) 0.101(5) 0.056(4) 0.019(3) 0.021(4) 0.002(5) C13 0.082(4) 0.121(5) 0.053(3) -0.004(4) -0.007(4) 0.000(4) C14 0.066(4) 0.084(4) 0.059(3) -0.009(3) -0.002(3) -0.005(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 Br1 C8 1.914(4) . ? S2 C8 1.749(5) . ? S2 C9 1.780(4) . ? C1 C2 1.366(7) . ? C1 C6 1.368(7) . ? C1 H1A 0.9300 . ? C2 C3 1.383(6) . ? C2 H2A 0.9300 . ? C3 C4 1.387(6) . ? C3 H3A 0.9300 . ? C4 C5 1.386(5) . ? C4 C7 1.479(5) . ? C5 C6 1.364(6) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.325(5) . ? C7 H7A 0.9300 . ? C9 C14 1.355(6) . ? C9 C10 1.381(6) . ? C10 C11 1.385(6) . ? C10 H10A 0.9300 . ? C11 C12 1.387(8) . ? C11 H11A 0.9300 . ? C12 C13 1.376(8) . ? C12 H12A 0.9300 . ? C13 C14 1.369(7) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? 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 C8 S2 C9 102.4(2) . . ? C2 C1 C6 119.6(5) . . ? C2 C1 H1A 120.2 . . ? C6 C1 H1A 120.2 . . ? C1 C2 C3 120.2(5) . . ? C1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? C2 C3 C4 120.9(5) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? C5 C4 C3 117.3(4) . . ? C5 C4 C7 117.0(4) . . ? C3 C4 C7 125.7(4) . . ? C6 C5 C4 121.5(5) . . ? C6 C5 H5A 119.3 . . ? C4 C5 H5A 119.3 . . ? C5 C6 C1 120.5(5) . . ? C5 C6 H6A 119.8 . . ? C1 C6 H6A 119.8 . . ? C8 C7 C4 132.1(4) . . ? C8 C7 H7A 113.9 . . ? C4 C7 H7A 113.9 . . ? C7 C8 S2 128.0(4) . . ? C7 C8 Br1 117.3(3) . . ? S2 C8 Br1 114.2(2) . . ? C14 C9 C10 120.3(4) . . ? C14 C9 S2 123.0(4) . . ? C10 C9 S2 116.6(4) . . ? C9 C10 C11 120.5(5) . . ? C9 C10 H10A 119.7 . . ? C11 C10 H10A 119.7 . . ? C10 C11 C12 118.2(6) . . ? C10 C11 H11A 120.9 . . ? C12 C11 H11A 120.9 . . ? C13 C12 C11 120.6(6) . . ? C13 C12 H12A 119.7 . . ? C11 C12 H12A 119.7 . . ? C14 C13 C12 120.0(6) . . ? C14 C13 H13A 120.0 . . ? C12 C13 H13A 120.0 . . ? C9 C14 C13 120.3(5) . . ? C9 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? 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 C6 C1 C2 C3 -0.5(9) . . . . ? C1 C2 C3 C4 1.6(8) . . . . ? C2 C3 C4 C5 -0.3(7) . . . . ? C2 C3 C4 C7 178.6(4) . . . . ? C3 C4 C5 C6 -2.0(7) . . . . ? C7 C4 C5 C6 179.0(4) . . . . ? C4 C5 C6 C1 3.1(8) . . . . ? C2 C1 C6 C5 -1.7(8) . . . . ? C5 C4 C7 C8 174.8(4) . . . . ? C3 C4 C7 C8 -4.1(7) . . . . ? C4 C7 C8 S2 7.6(7) . . . . ? C4 C7 C8 Br1 179.2(3) . . . . ? C9 S2 C8 C7 -123.3(4) . . . . ? C9 S2 C8 Br1 65.0(3) . . . . ? C8 S2 C9 C14 33.8(5) . . . . ? C8 S2 C9 C10 -148.5(3) . . . . ? C14 C9 C10 C11 0.2(7) . . . . ? S2 C9 C10 C11 -177.5(4) . . . . ? C9 C10 C11 C12 -1.1(7) . . . . ? C10 C11 C12 C13 0.6(8) . . . . ? C11 C12 C13 C14 0.8(9) . . . . ? C10 C9 C14 C13 1.1(7) . . . . ? S2 C9 C14 C13 178.7(4) . . . . ? C12 C13 C14 C9 -1.6(8) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.573 _refine_diff_density_min -0.371 _refine_diff_density_rms 0.059