# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email alessandro.massi@unife.it _publ_contact_author_name A.Massi loop_ _publ_author_name V.Bertolasi O.Bortolini A.Donvito G.Fantin M.Fogagnolo ; P.P.Giovannini ; A.Massi S.Pacifico data_16b _database_code_depnum_ccdc_archive 'CCDC 875932' #TrackingRef '- 16b revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 Br N O S' _chemical_formula_sum 'C18 H16 Br N O S' _chemical_formula_weight 374.29 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 12.0158(5) _cell_length_b 9.3261(4) _cell_length_c 14.7056(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.300(3) _cell_angle_gamma 90.00 _cell_volume 1630.66(12) _cell_formula_units_Z 4 _cell_measurement_temperature 295 _cell_measurement_reflns_used 9687 _cell_measurement_theta_min 4.37 _cell_measurement_theta_max 26.00 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 2.650 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.588 _exptl_absorpt_correction_T_max 0.859 _exptl_absorpt_process_details 'SORTAV (R.H. Blessing, Acta Crystallogr., 1995, A51, 33)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _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 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9687 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.37 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3147 _reflns_number_gt 2242 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'Denzo-SMN (otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995)' _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^)+(0.0528P)^2^+0.2560P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3147 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1098 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 N1 N 0.21457(18) 0.2396(2) 0.99360(15) 0.0452(5) Uani 1 1 d . . . C1 C 0.1415(2) 0.2113(3) 0.91494(18) 0.0461(6) Uani 1 1 d . . . O1 O 0.16918(17) 0.1416(2) 0.85153(13) 0.0606(5) Uani 1 1 d . . . C2 C 0.0247(2) 0.2774(3) 0.90791(18) 0.0462(6) Uani 1 1 d . . . S1 S -0.03483(6) 0.24058(9) 1.01264(5) 0.0544(2) Uani 1 1 d . . . C3 C 0.0772(3) 0.3059(3) 1.08974(19) 0.0499(7) Uani 1 1 d . . . C4 C 0.1825(2) 0.3048(3) 1.07321(18) 0.0472(6) Uani 1 1 d . . . C5 C 0.2743(3) 0.3698(5) 1.1408(3) 0.0649(9) Uani 1 1 d . . . C6 C 0.3336(2) 0.1982(4) 0.9945(2) 0.0514(7) Uani 1 1 d . . . C7 C 0.3698(2) 0.0709(3) 1.05443(18) 0.0480(7) Uani 1 1 d . . . C8 C 0.3075(3) -0.0536(4) 1.0490(2) 0.0610(8) Uani 1 1 d . . . C9 C 0.3453(4) -0.1709(5) 1.1017(3) 0.0775(11) Uani 1 1 d . . . C10 C 0.4456(4) -0.1644(5) 1.1605(3) 0.0827(13) Uani 1 1 d . . . C11 C 0.5084(4) -0.0415(5) 1.1658(3) 0.0831(12) Uani 1 1 d . . . C12 C 0.4703(3) 0.0760(4) 1.1136(2) 0.0664(9) Uani 1 1 d . . . C13 C -0.0571(2) 0.2215(3) 0.82835(17) 0.0437(6) Uani 1 1 d . . . C14 C -0.0823(3) 0.0766(3) 0.8199(2) 0.0523(7) Uani 1 1 d . . . C15 C -0.1642(3) 0.0265(4) 0.7514(2) 0.0563(8) Uani 1 1 d . . . C16 C -0.2212(2) 0.1228(3) 0.69085(18) 0.0527(7) Uani 1 1 d . . . C17 C -0.1963(3) 0.2672(4) 0.6962(2) 0.0554(8) Uani 1 1 d . . . C18 C -0.1139(2) 0.3166(3) 0.76465(18) 0.0483(6) Uani 1 1 d . . . Br1 Br -0.33816(3) 0.05626(5) 0.60053(3) 0.0885(2) Uani 1 1 d . . . H2 H 0.036(2) 0.387(3) 0.9040(16) 0.038(6) Uiso 1 1 d . . . H3 H 0.058(2) 0.337(3) 1.146(2) 0.050(8) Uiso 1 1 d . . . H51 H 0.308(3) 0.445(4) 1.114(2) 0.069(11) Uiso 1 1 d . . . H52 H 0.240(3) 0.407(4) 1.191(3) 0.078(11) Uiso 1 1 d . . . H53 H 0.333(3) 0.305(5) 1.161(2) 0.081(11) Uiso 1 1 d . . . H61 H 0.342(2) 0.179(3) 0.934(2) 0.050(8) Uiso 1 1 d . . . H62 H 0.379(2) 0.280(3) 1.0142(19) 0.050(8) Uiso 1 1 d . . . H8 H 0.239(3) -0.054(3) 1.008(2) 0.072(10) Uiso 1 1 d . . . H9 H 0.301(4) -0.254(5) 1.095(3) 0.099(14) Uiso 1 1 d . . . H10 H 0.471(3) -0.250(5) 1.194(3) 0.096(13) Uiso 1 1 d . . . H11 H 0.582(4) -0.037(5) 1.216(3) 0.114(15) Uiso 1 1 d . . . H12 H 0.516(3) 0.171(5) 1.118(3) 0.098(13) Uiso 1 1 d . . . H14 H -0.046(2) 0.011(4) 0.862(2) 0.056(8) Uiso 1 1 d . . . H15 H -0.187(2) -0.071(4) 0.747(2) 0.057(8) Uiso 1 1 d . . . H17 H -0.232(2) 0.328(3) 0.654(2) 0.054(8) Uiso 1 1 d . . . H18 H -0.095(3) 0.417(4) 0.766(2) 0.065(9) 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 N1 0.0451(12) 0.0455(14) 0.0441(11) -0.0004(10) 0.0035(10) 0.0031(10) C1 0.0516(15) 0.0423(17) 0.0452(14) 0.0035(12) 0.0089(12) 0.0027(12) O1 0.0597(12) 0.0747(16) 0.0476(11) -0.0124(10) 0.0082(9) 0.0105(11) C2 0.0531(15) 0.0392(18) 0.0461(14) 0.0015(11) 0.0066(12) 0.0029(12) S1 0.0516(4) 0.0647(5) 0.0473(4) -0.0048(3) 0.0082(3) -0.0040(3) C3 0.0614(19) 0.0481(18) 0.0394(14) -0.0059(12) 0.0049(13) 0.0031(14) C4 0.0560(17) 0.0395(16) 0.0443(14) -0.0013(11) 0.0013(12) 0.0027(12) C5 0.060(2) 0.067(3) 0.064(2) -0.0185(19) -0.0010(18) -0.003(2) C6 0.0472(16) 0.055(2) 0.0524(17) 0.0027(14) 0.0082(14) -0.0029(14) C7 0.0442(14) 0.0531(19) 0.0472(15) -0.0014(12) 0.0084(12) 0.0047(13) C8 0.0559(18) 0.060(2) 0.0653(19) 0.0044(15) 0.0040(16) 0.0006(16) C9 0.085(3) 0.059(3) 0.092(3) 0.011(2) 0.028(2) 0.008(2) C10 0.093(3) 0.083(3) 0.075(2) 0.025(2) 0.024(2) 0.038(3) C11 0.075(2) 0.100(4) 0.069(2) 0.009(2) -0.007(2) 0.027(2) C12 0.0542(17) 0.072(3) 0.069(2) -0.0045(17) -0.0033(16) 0.0072(17) C13 0.0498(14) 0.0398(17) 0.0411(13) 0.0003(11) 0.0048(11) 0.0043(12) C14 0.0635(17) 0.0419(18) 0.0494(16) 0.0037(13) 0.0016(14) 0.0107(14) C15 0.072(2) 0.0399(19) 0.0562(17) -0.0074(13) 0.0075(15) 0.0005(15) C16 0.0605(17) 0.052(2) 0.0435(14) -0.0115(13) 0.0012(13) 0.0072(15) C17 0.0634(18) 0.057(2) 0.0440(15) 0.0065(14) 0.0009(14) 0.0132(15) C18 0.0564(16) 0.0402(18) 0.0477(15) 0.0019(12) 0.0058(13) 0.0057(13) Br1 0.0924(3) 0.0850(3) 0.0773(3) -0.0293(2) -0.0248(2) 0.0073(2) _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 N1 C1 1.373(3) . ? N1 C4 1.421(3) . ? N1 C6 1.480(4) . ? C1 O1 1.222(3) . ? C1 C2 1.523(4) . ? C2 C13 1.508(4) . ? C2 S1 1.822(3) . ? C2 H2 1.03(3) . ? S1 C3 1.740(3) . ? C3 C4 1.322(4) . ? C3 H3 0.94(3) . ? C4 C5 1.502(4) . ? C5 H51 0.92(4) . ? C5 H52 0.96(4) . ? C5 H53 0.95(4) . ? C6 C7 1.504(4) . ? C6 H61 0.92(3) . ? C6 H62 0.95(3) . ? C7 C8 1.377(4) . ? C7 C12 1.384(4) . ? C8 C9 1.379(5) . ? C8 H8 0.95(4) . ? C9 C10 1.379(6) . ? C9 H9 0.94(5) . ? C10 C11 1.369(6) . ? C10 H10 0.97(4) . ? C11 C12 1.378(5) . ? C11 H11 1.07(5) . ? C12 H12 1.03(5) . ? C13 C14 1.386(4) . ? C13 C18 1.395(4) . ? C14 C15 1.384(4) . ? C14 H14 0.93(3) . ? C15 C16 1.376(4) . ? C15 H15 0.95(3) . ? C16 C17 1.380(4) . ? C16 Br1 1.893(3) . ? C17 C18 1.384(4) . ? C17 H17 0.90(3) . ? C18 H18 0.97(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 C1 N1 C4 124.0(2) . . ? C1 N1 C6 117.2(2) . . ? C4 N1 C6 118.7(2) . . ? O1 C1 N1 122.3(2) . . ? O1 C1 C2 120.9(2) . . ? N1 C1 C2 116.8(2) . . ? C13 C2 C1 113.8(2) . . ? C13 C2 S1 107.45(19) . . ? C1 C2 S1 109.66(18) . . ? C13 C2 H2 112.0(13) . . ? C1 C2 H2 106.0(13) . . ? S1 C2 H2 107.7(13) . . ? C3 S1 C2 97.11(14) . . ? C4 C3 S1 123.2(2) . . ? C4 C3 H3 121.7(17) . . ? S1 C3 H3 114.9(17) . . ? C3 C4 N1 122.4(2) . . ? C3 C4 C5 120.4(3) . . ? N1 C4 C5 117.2(3) . . ? C4 C5 H51 110(2) . . ? C4 C5 H52 108(2) . . ? H51 C5 H52 109(3) . . ? C4 C5 H53 113(2) . . ? H51 C5 H53 105(3) . . ? H52 C5 H53 112(3) . . ? N1 C6 C7 114.1(2) . . ? N1 C6 H61 106.3(17) . . ? C7 C6 H61 110.3(19) . . ? N1 C6 H62 107.5(17) . . ? C7 C6 H62 110.4(18) . . ? H61 C6 H62 108(2) . . ? C8 C7 C12 118.9(3) . . ? C8 C7 C6 121.5(3) . . ? C12 C7 C6 119.5(3) . . ? C7 C8 C9 120.3(3) . . ? C7 C8 H8 117(2) . . ? C9 C8 H8 122(2) . . ? C10 C9 C8 120.3(4) . . ? C10 C9 H9 122(3) . . ? C8 C9 H9 117(3) . . ? C11 C10 C9 119.8(4) . . ? C11 C10 H10 122(2) . . ? C9 C10 H10 118(3) . . ? C10 C11 C12 119.9(4) . . ? C10 C11 H11 118(2) . . ? C12 C11 H11 122(3) . . ? C11 C12 C7 120.8(4) . . ? C11 C12 H12 121(2) . . ? C7 C12 H12 118(2) . . ? C14 C13 C18 118.7(3) . . ? C14 C13 C2 121.1(2) . . ? C18 C13 C2 120.2(3) . . ? C15 C14 C13 121.2(3) . . ? C15 C14 H14 118(2) . . ? C13 C14 H14 120(2) . . ? C16 C15 C14 119.1(3) . . ? C16 C15 H15 118.1(18) . . ? C14 C15 H15 122.6(18) . . ? C15 C16 C17 121.1(3) . . ? C15 C16 Br1 119.4(2) . . ? C17 C16 Br1 119.6(2) . . ? C16 C17 C18 119.5(3) . . ? C16 C17 H17 119.9(19) . . ? C18 C17 H17 120.5(19) . . ? C17 C18 C13 120.4(3) . . ? C17 C18 H18 119.1(19) . . ? C13 C18 H18 120.5(19) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.256 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.063