# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global #TrackingRef '- data-bo1612.cif' _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Wen Yang' 'Da-Ming Du' _publ_contact_author_name 'Da-Ming Du' _publ_contact_author_email dudm@bit.edu.cn data_bo1612 _database_code_depnum_ccdc_archive 'CCDC 886084' #TrackingRef '- data-bo1612.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 Br N O3 S' _chemical_formula_weight 318.19 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.2760(12) _cell_length_b 14.278(3) _cell_length_c 17.698(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1333.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 3226 _cell_measurement_theta_min 2.302 _cell_measurement_theta_max 29.124 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 3.235 _exptl_absorpt_correction_type Multi-scans _exptl_absorpt_correction_T_min 0.2692 _exptl_absorpt_correction_T_max 0.4925 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6454 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0988 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 29.13 _reflns_number_total 3332 _reflns_number_gt 2206 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0033P)^2^+-0.2290P] 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 ? _chemical_absolute_configuration ad _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.007(7) _refine_ls_number_reflns 3332 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0278 _refine_ls_wR_factor_gt 0.0263 _refine_ls_goodness_of_fit_ref 0.783 _refine_ls_restrained_S_all 0.783 _refine_ls_shift/su_max 0.002 _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 0.42511(6) 0.23450(2) 0.688970(16) 0.04094(10) Uani 1 1 d . . . S1 S 0.50796(12) 0.47749(5) 0.35512(4) 0.0298(2) Uani 1 1 d . . . O1 O 0.0969(3) 0.48957(13) 0.26957(10) 0.0366(5) Uani 1 1 d . . . O2 O -0.0683(4) 0.61667(12) 0.51141(10) 0.0304(5) Uani 1 1 d . . . O3 O 0.2499(3) 0.69484(13) 0.55723(10) 0.0356(6) Uani 1 1 d . . . N1 N 0.1527(5) 0.64480(16) 0.50901(13) 0.0236(6) Uani 1 1 d . . . C1 C 0.3687(5) 0.32355(19) 0.61131(15) 0.0236(7) Uani 1 1 d . . . C2 C 0.1705(5) 0.31061(19) 0.56125(16) 0.0305(8) Uani 1 1 d . . . H2 H 0.0588 0.2589 0.5669 0.037 Uiso 1 1 calc R . . C3 C 0.1367(5) 0.37386(18) 0.50281(15) 0.0258(7) Uani 1 1 d . . . H3 H -0.0014 0.3658 0.4690 0.031 Uiso 1 1 calc R . . C4 C 0.3006(5) 0.44885(19) 0.49263(14) 0.0201(7) Uani 1 1 d . . . C5 C 0.4966(5) 0.45898(19) 0.54482(14) 0.0307(8) Uani 1 1 d . . . H5 H 0.6105 0.5102 0.5400 0.037 Uiso 1 1 calc R . . C6 C 0.5289(5) 0.39626(19) 0.60337(15) 0.0299(8) Uani 1 1 d . . . H6 H 0.6644 0.4044 0.6381 0.036 Uiso 1 1 calc R . . C7 C 0.2736(5) 0.51243(19) 0.42546(14) 0.0216(7) Uani 1 1 d . . . H7 H 0.1007 0.5035 0.4035 0.026 Uiso 1 1 calc R . . C8 C 0.3205(4) 0.4717(2) 0.27128(15) 0.0272(8) Uani 1 1 d . . . C9 C 0.4729(5) 0.44016(19) 0.20408(13) 0.0358(8) Uani 1 1 d . . . H9A H 0.4315 0.4795 0.1604 0.043 Uiso 1 1 calc R . . H9B H 0.4325 0.3747 0.1926 0.043 Uiso 1 1 calc R . . H9C H 0.6540 0.4458 0.2155 0.043 Uiso 1 1 calc R . . C10 C 0.3126(5) 0.61751(19) 0.44166(14) 0.0221(7) Uani 1 1 d . . . H10 H 0.4953 0.6295 0.4532 0.026 Uiso 1 1 calc R . . C11 C 0.2288(5) 0.68018(18) 0.37633(14) 0.0339(8) Uani 1 1 d . . . H11A H 0.2383 0.7459 0.3919 0.041 Uiso 1 1 calc R . . H11B H 0.0539 0.6649 0.3623 0.041 Uiso 1 1 calc R . . H11C H 0.3404 0.6699 0.3328 0.041 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 0.0666(2) 0.02785(17) 0.02834(15) 0.00565(16) -0.00050(18) -0.00209(19) S1 0.0273(5) 0.0381(5) 0.0240(4) -0.0057(4) 0.0011(4) 0.0054(4) O1 0.0305(12) 0.0470(15) 0.0322(11) 0.0013(11) -0.0007(11) -0.0039(13) O2 0.0195(10) 0.0290(12) 0.0427(12) -0.0024(10) 0.0095(11) -0.0009(11) O3 0.0435(14) 0.0329(15) 0.0306(12) -0.0093(11) 0.0008(12) -0.0061(11) N1 0.0305(16) 0.0158(15) 0.0245(14) 0.0031(11) 0.0021(13) 0.0038(13) C1 0.0295(19) 0.0201(17) 0.0213(14) -0.0018(13) 0.0052(15) 0.0025(15) C2 0.037(2) 0.0176(18) 0.0373(18) -0.0017(15) 0.0072(17) -0.0070(15) C3 0.0246(17) 0.0241(18) 0.0287(16) -0.0041(14) -0.0068(15) -0.0022(15) C4 0.0184(16) 0.0161(17) 0.0257(16) -0.0011(13) 0.0066(14) 0.0033(13) C5 0.0319(19) 0.0208(18) 0.0394(17) 0.0057(14) -0.0062(16) -0.0136(15) C6 0.030(2) 0.0286(19) 0.0315(16) 0.0013(14) -0.0086(15) -0.0010(17) C7 0.0185(15) 0.0234(19) 0.0229(15) -0.0014(14) 0.0019(13) -0.0024(14) C8 0.039(2) 0.0163(18) 0.0263(16) 0.0021(14) 0.0061(16) -0.0076(17) C9 0.0434(19) 0.039(2) 0.0248(16) -0.0037(14) -0.0008(16) 0.0015(16) C10 0.0219(19) 0.0213(18) 0.0230(15) 0.0005(14) 0.0090(14) -0.0012(14) C11 0.0426(19) 0.0256(19) 0.0336(18) 0.0052(16) 0.0065(17) 0.0016(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 Br1 C1 1.896(3) . ? S1 C8 1.785(3) . ? S1 C7 1.824(2) . ? O1 C8 1.208(3) . ? O2 N1 1.234(2) . ? O3 N1 1.225(3) . ? N1 C10 1.512(3) . ? C1 C6 1.346(3) . ? C1 C2 1.383(3) . ? C2 C3 1.385(3) . ? C2 H2 0.9500 . ? C3 C4 1.388(3) . ? C3 H3 0.9500 . ? C4 C5 1.394(3) . ? C4 C7 1.503(3) . ? C5 C6 1.380(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C10 1.541(3) . ? C7 H7 1.0000 . ? C8 C9 1.504(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.527(3) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? 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 S1 C7 101.80(11) . . ? O3 N1 O2 124.1(2) . . ? O3 N1 C10 117.8(2) . . ? O2 N1 C10 118.1(2) . . ? C6 C1 C2 120.7(3) . . ? C6 C1 Br1 119.6(2) . . ? C2 C1 Br1 119.6(2) . . ? C1 C2 C3 119.3(3) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C2 C3 C4 121.3(3) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C3 C4 C5 117.2(3) . . ? C3 C4 C7 120.6(2) . . ? C5 C4 C7 122.1(3) . . ? C6 C5 C4 121.4(3) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C1 C6 C5 120.1(3) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C4 C7 C10 115.4(2) . . ? C4 C7 S1 108.09(19) . . ? C10 C7 S1 107.62(18) . . ? C4 C7 H7 108.5 . . ? C10 C7 H7 108.5 . . ? S1 C7 H7 108.5 . . ? O1 C8 C9 124.5(3) . . ? O1 C8 S1 123.5(2) . . ? C9 C8 S1 112.01(18) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 C11 106.5(2) . . ? N1 C10 C7 108.9(2) . . ? C11 C10 C7 113.0(2) . . ? N1 C10 H10 109.5 . . ? C11 C10 H10 109.5 . . ? C7 C10 H10 109.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 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 C6 C1 C2 C3 -0.5(4) . . . . ? Br1 C1 C2 C3 -177.4(2) . . . . ? C1 C2 C3 C4 1.3(4) . . . . ? C2 C3 C4 C5 -1.5(4) . . . . ? C2 C3 C4 C7 175.1(2) . . . . ? C3 C4 C5 C6 1.0(4) . . . . ? C7 C4 C5 C6 -175.6(2) . . . . ? C2 C1 C6 C5 0.0(4) . . . . ? Br1 C1 C6 C5 176.9(2) . . . . ? C4 C5 C6 C1 -0.3(4) . . . . ? C3 C4 C7 C10 139.5(3) . . . . ? C5 C4 C7 C10 -44.0(4) . . . . ? C3 C4 C7 S1 -100.0(3) . . . . ? C5 C4 C7 S1 76.5(3) . . . . ? C8 S1 C7 C4 131.66(19) . . . . ? C8 S1 C7 C10 -103.1(2) . . . . ? C7 S1 C8 O1 0.9(3) . . . . ? C7 S1 C8 C9 -178.0(2) . . . . ? O3 N1 C10 C11 -101.8(3) . . . . ? O2 N1 C10 C11 77.0(3) . . . . ? O3 N1 C10 C7 136.0(3) . . . . ? O2 N1 C10 C7 -45.2(3) . . . . ? C4 C7 C10 N1 -49.6(3) . . . . ? S1 C7 C10 N1 -170.38(15) . . . . ? C4 C7 C10 C11 -167.8(2) . . . . ? S1 C7 C10 C11 71.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.740 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.068