# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Daniel Mendoza-Espinosa' _publ_contact_author_email danielme1982@gmail.com loop_ _publ_author_name D.Mendoza-Espinosa G.Ung B.Donnadieu G.Bertrand data_shelxl _database_code_depnum_ccdc_archive 'CCDC 833533' #TrackingRef '- 3b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C24H22NS,C3H6O,H2O,Br _chemical_formula_sum 'C27 H30 Br N O2 S' _chemical_formula_weight 512.49 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)/c _symmetry_space_group_name_Hall -P2ybc 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 9.4960(14) _cell_length_b 28.054(4) _cell_length_c 9.6399(14) _cell_angle_alpha 90.00 _cell_angle_beta 104.693(2) _cell_angle_gamma 90.00 _cell_volume 2484.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8162 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 28.98 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 1.763 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6024 _exptl_absorpt_correction_T_max 0.8435 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20859 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 29.28 _reflns_number_total 6277 _reflns_number_gt 5167 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0709P)^2^+0.5969P] 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 6277 _refine_ls_number_parameters 378 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _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 0.74437(2) 0.299004(8) 0.12872(3) 0.02022(9) Uani 1 1 d . . . S1A S 0.53240(9) 0.20868(4) 0.23735(13) 0.0161(2) Uani 0.80 1 d P A 1 C1A C 0.5693(6) 0.1750(2) 0.1021(7) 0.0180(14) Uiso 0.80 1 d P A 1 S1B S 0.5900(5) 0.1840(2) 0.1085(6) 0.0189(10) Uani 0.20 1 d P A 2 C1B C 0.500(2) 0.2054(9) 0.232(3) 0.0180(14) Uiso 0.20 1 d P A 2 O1 O 0.7943(4) 0.46740(9) 1.0414(4) 0.0700(9) Uani 1 1 d . . . N1 N 0.35191(18) 0.14560(6) 0.1210(2) 0.0124(4) Uani 1 1 d . A . C2 C 0.3747(2) 0.17953(8) 0.2252(2) 0.0140(4) Uani 1 1 d . . . C3 C 0.4621(2) 0.14267(8) 0.0490(2) 0.0145(4) Uani 1 1 d . . . C4 C 0.4622(2) 0.10951(8) -0.0693(2) 0.0143(4) Uani 1 1 d . A . C5 C 0.4116(2) 0.06246(8) -0.0725(3) 0.0171(4) Uani 1 1 d . . . C6 C 0.4176(3) 0.03302(8) -0.1868(3) 0.0197(5) Uani 1 1 d . A . C7 C 0.4747(3) 0.04931(9) -0.2971(3) 0.0201(5) Uani 1 1 d . . . C8 C 0.5280(3) 0.09552(9) -0.2924(3) 0.0201(5) Uani 1 1 d . A . C9 C 0.5212(2) 0.12558(8) -0.1798(3) 0.0177(4) Uani 1 1 d . . . C10 C 0.2769(2) 0.19040(8) 0.3174(2) 0.0137(4) Uani 1 1 d . A . C11 C 0.3395(2) 0.19742(8) 0.4639(3) 0.0160(4) Uani 1 1 d . . . C12 C 0.2505(3) 0.20660(8) 0.5548(3) 0.0176(4) Uani 1 1 d . A . C13 C 0.1001(3) 0.20970(8) 0.5013(3) 0.0182(5) Uani 1 1 d . . . C14 C 0.0392(3) 0.20425(8) 0.3553(3) 0.0173(5) Uani 1 1 d . A . C15 C 0.1258(2) 0.19436(8) 0.2622(3) 0.0156(4) Uani 1 1 d . . . C16 C 0.2203(2) 0.11630(7) 0.0885(2) 0.0128(4) Uani 1 1 d . . . C17 C 0.2069(2) 0.08110(8) 0.1866(2) 0.0144(4) Uani 1 1 d . A . C18 C 0.0754(2) 0.05616(8) 0.1583(3) 0.0160(4) Uani 1 1 d . . . C19 C -0.0376(2) 0.06604(8) 0.0372(3) 0.0165(4) Uani 1 1 d . A . C20 C -0.0165(2) 0.10072(8) -0.0593(3) 0.0165(4) Uani 1 1 d . . . C21 C 0.1121(2) 0.12680(8) -0.0359(2) 0.0138(4) Uani 1 1 d . A . C22 C 0.3269(3) 0.06982(9) 0.3181(3) 0.0192(5) Uani 1 1 d . . . C23 C -0.1814(3) 0.04021(9) 0.0122(3) 0.0244(5) Uani 1 1 d . . . C24 C 0.1321(3) 0.16502(8) -0.1386(3) 0.0179(5) Uani 1 1 d . . . C25 C 0.8632(4) 0.43651(10) 1.0005(4) 0.0361(7) Uani 1 1 d . . . C26 C 1.0206(4) 0.42861(14) 1.0662(4) 0.0459(8) Uani 1 1 d . . . C27 C 0.7929(4) 0.40381(12) 0.8810(4) 0.0375(7) Uani 1 1 d . . . O1W O 0.8409(2) 0.20215(6) 0.9865(2) 0.0264(4) Uani 1 1 d . . . H5 H 0.376(3) 0.0492(11) -0.006(4) 0.0333(16) Uiso 1 1 d . . . H6 H 0.379(3) 0.0035(11) -0.188(3) 0.0333(16) Uiso 1 1 d . . . H7 H 0.480(3) 0.0304(11) -0.367(4) 0.0333(16) Uiso 1 1 d . . . H8 H 0.570(3) 0.1060(11) -0.364(4) 0.0333(16) Uiso 1 1 d . . . H9 H 0.551(3) 0.1575(11) -0.177(4) 0.0333(16) Uiso 1 1 d . . . H11 H 0.433(4) 0.1950(11) 0.509(4) 0.0333(16) Uiso 1 1 d . . . H12 H 0.283(4) 0.2132(12) 0.650(4) 0.0333(16) Uiso 1 1 d . . . H13 H 0.046(3) 0.2169(12) 0.562(4) 0.0333(16) Uiso 1 1 d . . . H14 H -0.046(4) 0.2099(11) 0.325(4) 0.0333(16) Uiso 1 1 d . . . H15 H 0.089(4) 0.1937(11) 0.164(4) 0.0333(16) Uiso 1 1 d . . . H18 H 0.063(3) 0.0308(11) 0.227(4) 0.0333(16) Uiso 1 1 d . . . H20 H -0.092(3) 0.1088(11) -0.158(4) 0.0333(16) Uiso 1 1 d . . . H22A H 0.330(3) 0.0897(12) 0.393(4) 0.0333(16) Uiso 1 1 d . . . H22B H 0.422(4) 0.0645(11) 0.296(3) 0.0333(16) Uiso 1 1 d . . . H22C H 0.313(3) 0.0381(11) 0.367(4) 0.0333(16) Uiso 1 1 d . . . H23A H -0.255(3) 0.0589(11) 0.046(4) 0.0333(16) Uiso 1 1 d . . . H23B H -0.176(3) 0.0098(12) 0.067(4) 0.0333(16) Uiso 1 1 d . . . H23C H -0.226(3) 0.0309(12) -0.087(4) 0.0333(16) Uiso 1 1 d . . . H24A H 0.168(4) 0.1944(11) -0.100(4) 0.0333(16) Uiso 1 1 d . . . H24B H 0.042(4) 0.1747(11) -0.202(4) 0.0333(16) Uiso 1 1 d . . . H24C H 0.194(3) 0.1564(11) -0.207(4) 0.0333(16) Uiso 1 1 d . . . H26A H 1.081(4) 0.4424(12) 1.019(4) 0.0333(16) Uiso 1 1 d . . . H26B H 1.053(3) 0.3944(12) 1.081(3) 0.0333(16) Uiso 1 1 d . . . H26C H 1.062(4) 0.4442(12) 1.142(4) 0.0333(16) Uiso 1 1 d . . . H27A H 0.787(3) 0.3718(12) 0.926(4) 0.0333(16) Uiso 1 1 d . . . H27B H 0.854(4) 0.4021(11) 0.822(4) 0.0333(16) Uiso 1 1 d . . . H27C H 0.703(4) 0.4200(11) 0.844(4) 0.0333(16) Uiso 1 1 d . . . H12W H 0.8210 0.2331 1.0042 0.0333(16) Uiso 1 1 d . . . H112 H 0.8228 0.2023 0.8886 0.0333(16) Uiso 1 1 d . . . H1A H 0.6524 0.1809 0.0629 0.0333(16) 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 0.01370(12) 0.02686(14) 0.01927(14) -0.00365(9) 0.00266(9) 0.00047(8) S1A 0.0119(5) 0.0207(4) 0.0162(4) -0.0032(3) 0.0043(4) -0.0050(4) S1B 0.0118(17) 0.019(2) 0.027(2) -0.0061(16) 0.0068(14) -0.0064(16) O1 0.090(2) 0.0380(13) 0.098(2) -0.0125(14) 0.0531(19) 0.0145(14) N1 0.0109(8) 0.0138(8) 0.0122(9) 0.0014(7) 0.0023(7) -0.0021(6) C2 0.0132(9) 0.0162(10) 0.0117(11) 0.0018(8) 0.0016(8) -0.0003(8) C3 0.0124(9) 0.0167(10) 0.0148(11) 0.0021(8) 0.0039(8) 0.0009(8) C4 0.0109(9) 0.0175(10) 0.0137(11) 0.0001(8) 0.0018(8) 0.0009(7) C5 0.0156(10) 0.0191(11) 0.0175(12) 0.0021(9) 0.0060(9) -0.0008(8) C6 0.0192(11) 0.0171(10) 0.0231(13) -0.0014(9) 0.0058(9) -0.0005(9) C7 0.0230(11) 0.0231(11) 0.0138(11) -0.0024(9) 0.0040(9) 0.0040(9) C8 0.0228(11) 0.0252(12) 0.0138(12) 0.0033(9) 0.0072(9) 0.0032(9) C9 0.0167(10) 0.0191(11) 0.0182(12) 0.0026(9) 0.0061(9) -0.0001(8) C10 0.0139(10) 0.0136(9) 0.0140(11) 0.0013(8) 0.0042(8) -0.0005(7) C11 0.0132(10) 0.0178(10) 0.0158(11) -0.0001(8) 0.0015(8) -0.0011(8) C12 0.0205(11) 0.0193(10) 0.0129(11) 0.0001(8) 0.0041(9) -0.0004(8) C13 0.0198(11) 0.0182(10) 0.0193(12) 0.0008(9) 0.0098(9) 0.0000(8) C14 0.0118(10) 0.0182(10) 0.0217(12) 0.0004(9) 0.0038(9) 0.0012(8) C15 0.0137(10) 0.0171(10) 0.0145(11) 0.0001(8) 0.0009(8) -0.0005(8) C16 0.0094(9) 0.0157(10) 0.0134(10) -0.0015(8) 0.0032(8) -0.0022(7) C17 0.0140(9) 0.0153(10) 0.0141(11) 0.0006(8) 0.0039(8) 0.0010(8) C18 0.0163(10) 0.0155(10) 0.0178(11) 0.0014(8) 0.0071(9) -0.0020(8) C19 0.0131(10) 0.0162(10) 0.0208(12) -0.0033(8) 0.0054(9) -0.0027(8) C20 0.0132(10) 0.0197(10) 0.0161(11) -0.0023(8) 0.0030(8) 0.0013(8) C21 0.0146(9) 0.0157(10) 0.0114(10) 0.0000(8) 0.0042(8) 0.0013(8) C22 0.0173(10) 0.0223(11) 0.0157(12) 0.0059(9) 0.0002(9) 0.0006(9) C23 0.0139(11) 0.0246(12) 0.0343(15) -0.0016(11) 0.0054(10) -0.0049(9) C24 0.0176(10) 0.0200(11) 0.0146(11) 0.0044(9) 0.0016(9) -0.0006(8) C25 0.0539(18) 0.0202(12) 0.0421(18) 0.0044(12) 0.0267(15) 0.0028(12) C26 0.060(2) 0.0440(19) 0.0324(19) 0.0032(15) 0.0088(16) -0.0040(17) C27 0.0379(16) 0.0342(15) 0.0429(19) 0.0071(13) 0.0146(14) 0.0040(13) O1W 0.0260(9) 0.0284(9) 0.0251(10) -0.0018(7) 0.0069(8) -0.0004(7) _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 S1A C2 1.684(2) . ? S1A C1A 1.716(6) . ? C1A C3 1.363(6) . ? C1A H1A 0.972(6) . ? S1B C3 1.672(6) . ? S1B C1B 1.74(3) . ? S1B H1A 0.827(5) . ? C1B C2 1.38(2) . ? O1 C25 1.210(4) . ? N1 C2 1.361(3) . ? N1 C3 1.397(3) . ? N1 C16 1.462(3) . ? C2 C10 1.471(3) . ? C3 C4 1.472(3) . ? C4 C9 1.398(3) . ? C4 C5 1.403(3) . ? C5 C6 1.390(3) . ? C5 H5 0.88(3) . ? C6 C7 1.388(4) . ? C6 H6 0.91(3) . ? C7 C8 1.389(4) . ? C7 H7 0.87(3) . ? C8 C9 1.389(3) . ? C8 H8 0.93(3) . ? C9 H9 0.94(3) . ? C10 C11 1.400(3) . ? C10 C15 1.402(3) . ? C11 C12 1.387(3) . ? C11 H11 0.89(4) . ? C12 C13 1.393(3) . ? C12 H12 0.91(3) . ? C13 C14 1.388(4) . ? C13 H13 0.90(3) . ? C14 C15 1.390(3) . ? C14 H14 0.80(3) . ? C15 H15 0.92(4) . ? C16 C17 1.395(3) . ? C16 C21 1.398(3) . ? C17 C18 1.397(3) . ? C17 C22 1.507(3) . ? C18 C19 1.399(3) . ? C18 H18 1.00(3) . ? C19 C20 1.395(3) . ? C19 C23 1.510(3) . ? C20 C21 1.392(3) . ? C20 H20 1.06(3) . ? C21 C24 1.504(3) . ? C22 H22A 0.90(3) . ? C22 H22B 0.99(3) . ? C22 H22C 1.03(3) . ? C23 H23A 0.99(3) . ? C23 H23B 1.00(3) . ? C23 H23C 0.98(4) . ? C24 H24A 0.93(3) . ? C24 H24B 0.96(3) . ? C24 H24C 1.02(3) . ? C25 C26 1.485(5) . ? C25 C27 1.492(5) . ? C26 H26A 0.90(4) . ? C26 H26B 1.01(3) . ? C26 H26C 0.86(4) . ? C27 H27A 1.01(3) . ? C27 H27B 0.91(4) . ? C27 H27C 0.95(3) . ? O1W H12W 0.9140(18) . ? O1W H112 0.915(2) . ? 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 C2 S1A C1A 91.7(2) . . ? C3 C1A S1A 112.0(4) . . ? C3 C1A H1A 124.7(6) . . ? S1A C1A H1A 123.0(4) . . ? C3 S1B C1B 91.9(8) . . ? C3 S1B H1A 107.5(5) . . ? C1B S1B H1A 160.6(9) . . ? C2 C1B S1B 110.6(15) . . ? C2 N1 C3 114.16(17) . . ? C2 N1 C16 121.25(18) . . ? C3 N1 C16 124.58(18) . . ? N1 C2 C1B 112.2(11) . . ? N1 C2 C10 125.77(19) . . ? C1B C2 C10 121.9(11) . . ? N1 C2 S1A 111.27(16) . . ? C1B C2 S1A 3.0(10) . . ? C10 C2 S1A 122.95(17) . . ? C1A C3 N1 110.9(3) . . ? C1A C3 C4 124.4(3) . . ? N1 C3 C4 124.75(19) . . ? C1A C3 S1B 2.5(4) . . ? N1 C3 S1B 111.1(2) . . ? C4 C3 S1B 124.1(2) . . ? C9 C4 C5 119.2(2) . . ? C9 C4 C3 117.8(2) . . ? C5 C4 C3 123.0(2) . . ? C6 C5 C4 119.6(2) . . ? C6 C5 H5 115(2) . . ? C4 C5 H5 125(2) . . ? C7 C6 C5 121.0(2) . . ? C7 C6 H6 122(2) . . ? C5 C6 H6 117(2) . . ? C6 C7 C8 119.5(2) . . ? C6 C7 H7 120(2) . . ? C8 C7 H7 120(2) . . ? C7 C8 C9 120.2(2) . . ? C7 C8 H8 119(2) . . ? C9 C8 H8 120(2) . . ? C8 C9 C4 120.5(2) . . ? C8 C9 H9 122(2) . . ? C4 C9 H9 118(2) . . ? C11 C10 C15 120.2(2) . . ? C11 C10 C2 117.84(19) . . ? C15 C10 C2 121.9(2) . . ? C12 C11 C10 119.5(2) . . ? C12 C11 H11 114(2) . . ? C10 C11 H11 127(2) . . ? C11 C12 C13 120.6(2) . . ? C11 C12 H12 125(2) . . ? C13 C12 H12 114(2) . . ? C14 C13 C12 119.5(2) . . ? C14 C13 H13 122(2) . . ? C12 C13 H13 119(2) . . ? C13 C14 C15 121.0(2) . . ? C13 C14 H14 118(3) . . ? C15 C14 H14 121(3) . . ? C14 C15 C10 119.1(2) . . ? C14 C15 H15 122(2) . . ? C10 C15 H15 118(2) . . ? C17 C16 C21 123.84(19) . . ? C17 C16 N1 118.18(19) . . ? C21 C16 N1 117.91(19) . . ? C16 C17 C18 116.9(2) . . ? C16 C17 C22 122.64(19) . . ? C18 C17 C22 120.4(2) . . ? C17 C18 C19 121.5(2) . . ? C17 C18 H18 118.2(18) . . ? C19 C18 H18 120.3(18) . . ? C20 C19 C18 119.0(2) . . ? C20 C19 C23 120.4(2) . . ? C18 C19 C23 120.6(2) . . ? C21 C20 C19 121.8(2) . . ? C21 C20 H20 113.4(17) . . ? C19 C20 H20 124.7(17) . . ? C20 C21 C16 116.9(2) . . ? C20 C21 C24 121.3(2) . . ? C16 C21 C24 121.77(19) . . ? C17 C22 H22A 114(2) . . ? C17 C22 H22B 112.6(19) . . ? H22A C22 H22B 114(3) . . ? C17 C22 H22C 114.3(18) . . ? H22A C22 H22C 99(3) . . ? H22B C22 H22C 101(2) . . ? C19 C23 H23A 112.3(18) . . ? C19 C23 H23B 113.7(18) . . ? H23A C23 H23B 103(3) . . ? C19 C23 H23C 115.6(19) . . ? H23A C23 H23C 107(3) . . ? H23B C23 H23C 104(3) . . ? C21 C24 H24A 117(2) . . ? C21 C24 H24B 112.5(19) . . ? H24A C24 H24B 100(3) . . ? C21 C24 H24C 116.6(18) . . ? H24A C24 H24C 105(3) . . ? H24B C24 H24C 103(3) . . ? O1 C25 C26 122.5(3) . . ? O1 C25 C27 121.2(3) . . ? C26 C25 C27 116.3(3) . . ? C25 C26 H26A 115(2) . . ? C25 C26 H26B 116.3(18) . . ? H26A C26 H26B 106(3) . . ? C25 C26 H26C 119(2) . . ? H26A C26 H26C 90(3) . . ? H26B C26 H26C 108(3) . . ? C25 C27 H27A 106(2) . . ? C25 C27 H27B 106(2) . . ? H27A C27 H27B 110(3) . . ? C25 C27 H27C 100(2) . . ? H27A C27 H27C 117(3) . . ? H27B C27 H27C 116(3) . . ? H12W O1W H112 101.23(18) . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 29.28 _diffrn_measured_fraction_theta_full 0.927 _refine_diff_density_max 0.476 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.096 # Attachment '- 5b.cif' data_5b _database_code_depnum_ccdc_archive 'CCDC 833534' #TrackingRef '- 5b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H21 Au Cl N S' _chemical_formula_sum 'C24 H21 Au Cl N S' _chemical_formula_weight 587.89 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc 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 18.170(4) _cell_length_b 9.7695(15) _cell_length_c 24.734(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.134(3) _cell_angle_gamma 90.00 _cell_volume 4334.9(12) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9951 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 29.04 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.802 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2272 _exptl_absorpt_coefficient_mu 7.016 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.2531 _exptl_absorpt_correction_T_max 0.5405 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11994 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 29.23 _reflns_number_total 4607 _reflns_number_gt 4049 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0758P)^2^+228.0935P] 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 4607 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0648 _refine_ls_wR_factor_ref 0.2243 _refine_ls_wR_factor_gt 0.2058 _refine_ls_goodness_of_fit_ref 1.174 _refine_ls_restrained_S_all 1.174 _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 Au1 Au 0.08737(3) 0.94330(5) 0.54958(2) 0.03486(19) Uani 1 1 d . . . S1 S 0.0209(2) 0.6957(4) 0.46991(16) 0.0376(7) Uani 1 1 d . . . Cl1 Cl 0.0933(2) 1.0803(4) 0.62539(17) 0.0448(8) Uani 1 1 d . . . N1 N 0.1060(6) 0.7318(11) 0.4016(4) 0.027(2) Uani 1 1 d . . . C1 C 0.0835(8) 0.8250(14) 0.4830(6) 0.034(3) Uani 1 1 d . . . C2 C 0.0489(7) 0.6505(13) 0.4102(6) 0.031(3) Uani 1 1 d . . . C3 C 0.1278(5) 0.8295(10) 0.4433(4) 0.0170(18) Uani 1 1 d . . . C4 C 0.0142(8) 0.5395(13) 0.3745(6) 0.034(3) Uani 1 1 d . . . C5 C 0.0224(10) 0.4049(15) 0.3934(8) 0.045(4) Uani 1 1 d . . . H5 H 0.0506 0.3854 0.4283 0.054 Uiso 1 1 calc R . . C6 C -0.0103(12) 0.3021(17) 0.3614(10) 0.059(5) Uani 1 1 d . . . H6 H -0.0010 0.2095 0.3720 0.071 Uiso 1 1 calc R . . C7 C -0.0596(13) 0.334(2) 0.3108(10) 0.071(6) Uani 1 1 d . . . H7 H -0.0882 0.2639 0.2906 0.085 Uiso 1 1 calc R . . C8 C -0.0639(16) 0.466(2) 0.2927(12) 0.081(8) Uani 1 1 d . . . H8 H -0.0909 0.4877 0.2576 0.097 Uiso 1 1 calc R . . C9 C -0.0288(13) 0.5703(18) 0.3256(9) 0.060(5) Uani 1 1 d . . . H9 H -0.0347 0.6629 0.3140 0.072 Uiso 1 1 calc R . . C10 C 0.1898(7) 0.9241(13) 0.4391(5) 0.028(2) Uani 1 1 d . . . C11 C 0.2612(7) 0.8752(16) 0.4335(6) 0.035(3) Uani 1 1 d . . . H11 H 0.2704 0.7796 0.4319 0.042 Uiso 1 1 calc R . . C12 C 0.3179(10) 0.969(2) 0.4301(8) 0.055(5) Uani 1 1 d . . . H12 H 0.3644 0.9352 0.4231 0.066 Uiso 1 1 calc R . . C13 C 0.3106(16) 1.101(2) 0.4362(9) 0.080(8) Uani 1 1 d . . . H13 H 0.3522 1.1607 0.4366 0.096 Uiso 1 1 calc R . . C14 C 0.2390(14) 1.1547(18) 0.4421(9) 0.064(5) Uani 1 1 d . . . H14 H 0.2313 1.2507 0.4439 0.076 Uiso 1 1 calc R . . C15 C 0.1835(11) 1.0682(16) 0.4451(8) 0.049(4) Uani 1 1 d . . . H15 H 0.1371 1.1044 0.4516 0.059 Uiso 1 1 calc R . . C16 C 0.1414(7) 0.7157(13) 0.3532(5) 0.026(2) Uani 1 1 d . . . C17 C 0.1279(7) 0.8128(14) 0.3117(5) 0.030(2) Uani 1 1 d . . . C18 C 0.1650(8) 0.7972(14) 0.2661(6) 0.033(3) Uani 1 1 d . . . H18 H 0.1558 0.8615 0.2370 0.040 Uiso 1 1 calc R . . C19 C 0.2147(9) 0.6905(16) 0.2625(6) 0.040(3) Uani 1 1 d . . . C20 C 0.2290(9) 0.5994(15) 0.3073(7) 0.039(3) Uani 1 1 d . . . H20 H 0.2652 0.5296 0.3065 0.047 Uiso 1 1 calc R . . C21 C 0.1925(8) 0.6073(13) 0.3525(6) 0.032(3) Uani 1 1 d . . . C22 C 0.0766(10) 0.9341(17) 0.3136(8) 0.049(4) Uani 1 1 d . . . H22A H 0.0278 0.9020 0.3203 0.073 Uiso 1 1 calc R . . H22B H 0.0708 0.9829 0.2786 0.073 Uiso 1 1 calc R . . H22C H 0.0980 0.9961 0.3431 0.073 Uiso 1 1 calc R . . C23 C 0.2509(12) 0.677(2) 0.2126(8) 0.058(5) Uani 1 1 d . . . H23A H 0.2124 0.6736 0.1800 0.087 Uiso 1 1 calc R . . H23B H 0.2801 0.5919 0.2150 0.087 Uiso 1 1 calc R . . H23C H 0.2838 0.7550 0.2101 0.087 Uiso 1 1 calc R . . C24 C 0.2084(9) 0.5048(16) 0.3980(7) 0.041(3) Uani 1 1 d . . . H24A H 0.1830 0.4185 0.3866 0.062 Uiso 1 1 calc R . . H24B H 0.1902 0.5399 0.4306 0.062 Uiso 1 1 calc R . . H24C H 0.2622 0.4889 0.4065 0.062 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 Au1 0.0326(3) 0.0441(3) 0.0290(3) -0.0045(2) 0.0082(2) -0.0009(2) S1 0.0345(17) 0.0503(18) 0.0298(17) -0.0002(14) 0.0108(14) -0.0078(14) Cl1 0.0426(19) 0.056(2) 0.0363(19) -0.0152(15) 0.0077(16) 0.0004(15) N1 0.025(5) 0.034(5) 0.022(5) 0.001(4) 0.004(4) -0.001(4) C1 0.030(6) 0.044(7) 0.029(7) -0.005(5) 0.011(5) 0.000(5) C2 0.025(6) 0.038(6) 0.028(6) 0.001(5) 0.002(5) -0.009(5) C3 0.012(4) 0.023(4) 0.015(5) 0.005(4) -0.001(4) 0.004(3) C4 0.032(7) 0.034(6) 0.035(7) -0.002(5) 0.005(6) -0.006(5) C5 0.057(10) 0.036(7) 0.045(9) 0.003(6) 0.019(8) -0.011(6) C6 0.071(12) 0.037(8) 0.077(14) -0.006(8) 0.033(11) -0.019(8) C7 0.073(14) 0.057(11) 0.076(16) -0.020(10) -0.007(12) -0.014(10) C8 0.086(17) 0.059(12) 0.082(18) -0.023(11) -0.032(14) 0.003(11) C9 0.075(13) 0.044(9) 0.055(12) -0.007(8) -0.006(10) -0.006(8) C10 0.029(6) 0.038(6) 0.016(5) -0.001(4) 0.002(5) -0.004(5) C11 0.022(6) 0.051(8) 0.030(7) -0.002(6) -0.001(5) -0.007(5) C12 0.032(8) 0.089(13) 0.043(10) -0.001(9) 0.002(7) -0.017(8) C13 0.11(2) 0.074(13) 0.056(12) 0.005(10) 0.009(13) -0.073(14) C14 0.086(15) 0.039(8) 0.064(13) 0.012(8) 0.008(11) -0.025(9) C15 0.062(11) 0.040(7) 0.046(10) 0.014(6) 0.009(8) 0.002(7) C16 0.022(5) 0.038(6) 0.018(5) 0.001(4) 0.004(4) -0.002(4) C17 0.026(6) 0.041(6) 0.023(6) 0.003(5) 0.000(5) 0.001(5) C18 0.033(7) 0.043(7) 0.024(6) 0.002(5) 0.004(5) -0.002(5) C19 0.041(8) 0.051(8) 0.031(8) -0.008(6) 0.013(6) 0.003(6) C20 0.040(7) 0.039(7) 0.043(9) -0.004(6) 0.020(7) 0.004(5) C21 0.037(7) 0.030(6) 0.030(7) -0.002(5) 0.005(5) -0.005(5) C22 0.048(9) 0.052(9) 0.051(10) 0.019(7) 0.020(8) 0.013(7) C23 0.061(11) 0.084(13) 0.034(9) -0.007(8) 0.026(9) 0.005(9) C24 0.034(7) 0.045(7) 0.046(9) 0.012(7) 0.011(7) 0.009(6) _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 Au1 C1 2.005(14) . ? Au1 Cl1 2.293(4) . ? S1 C2 1.695(14) . ? S1 C1 1.697(14) . ? N1 C2 1.351(15) . ? N1 C3 1.414(15) . ? N1 C16 1.454(15) . ? C1 C3 1.364(16) . ? C2 C4 1.475(18) . ? C3 C10 1.473(15) . ? C4 C9 1.36(3) . ? C4 C5 1.40(2) . ? C5 C6 1.36(2) . ? C6 C7 1.45(3) . ? C7 C8 1.37(3) . ? C8 C9 1.39(3) . ? C10 C11 1.411(19) . ? C10 C15 1.423(19) . ? C11 C12 1.39(2) . ? C12 C13 1.31(3) . ? C13 C14 1.43(4) . ? C14 C15 1.33(3) . ? C16 C17 1.392(17) . ? C16 C21 1.410(18) . ? C17 C18 1.412(18) . ? C17 C22 1.513(19) . ? C18 C19 1.39(2) . ? C19 C20 1.41(2) . ? C19 C23 1.49(2) . ? C20 C21 1.390(19) . ? C21 C24 1.50(2) . ? 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 Au1 Cl1 179.2(4) . . ? C2 S1 C1 94.2(6) . . ? C2 N1 C3 114.5(10) . . ? C2 N1 C16 121.1(11) . . ? C3 N1 C16 124.4(10) . . ? C3 C1 S1 110.0(10) . . ? C3 C1 Au1 128.6(10) . . ? S1 C1 Au1 121.4(7) . . ? N1 C2 C4 127.2(12) . . ? N1 C2 S1 109.2(10) . . ? C4 C2 S1 123.6(10) . . ? C1 C3 N1 111.9(10) . . ? C1 C3 C10 128.0(11) . . ? N1 C3 C10 120.0(9) . . ? C9 C4 C5 121.3(15) . . ? C9 C4 C2 119.9(13) . . ? C5 C4 C2 118.6(15) . . ? C6 C5 C4 119.2(19) . . ? C5 C6 C7 119.9(18) . . ? C8 C7 C6 118.6(19) . . ? C7 C8 C9 120(2) . . ? C4 C9 C8 120.2(19) . . ? C11 C10 C15 115.9(13) . . ? C11 C10 C3 121.4(11) . . ? C15 C10 C3 122.6(13) . . ? C12 C11 C10 119.0(15) . . ? C13 C12 C11 123.7(19) . . ? C12 C13 C14 118.7(16) . . ? C15 C14 C13 119.1(17) . . ? C14 C15 C10 123.4(19) . . ? C17 C16 C21 122.8(12) . . ? C17 C16 N1 119.0(11) . . ? C21 C16 N1 118.0(11) . . ? C16 C17 C18 117.8(12) . . ? C16 C17 C22 123.2(12) . . ? C18 C17 C22 119.0(13) . . ? C19 C18 C17 122.0(13) . . ? C18 C19 C20 117.5(13) . . ? C18 C19 C23 119.8(16) . . ? C20 C19 C23 122.7(15) . . ? C21 C20 C19 123.0(13) . . ? C20 C21 C16 116.8(13) . . ? C20 C21 C24 120.5(13) . . ? C16 C21 C24 122.7(12) . . ? _diffrn_measured_fraction_theta_max 0.783 _diffrn_reflns_theta_full 29.23 _diffrn_measured_fraction_theta_full 0.783 _refine_diff_density_max 2.279 _refine_diff_density_min -2.230 _refine_diff_density_rms 0.372