# 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_x _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H27 N O S' _chemical_formula_sum 'C18 H27 N O S' _chemical_formula_weight 305.47 _chemical_absolute_configuration ad 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.208(5) _cell_length_b 6.102(3) _cell_length_c 13.056(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.438(7) _cell_angle_gamma 90.00 _cell_volume 905.3(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 1619 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 21.15 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.121 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.178 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9132 _exptl_absorpt_correction_T_max 0.9841 _exptl_absorpt_process_details 'Bruker/Siemens SADABS V2.03' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(1) _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 'CCD area detector' _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 7555 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0579 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3206 _reflns_number_gt 2776 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART V5.625' _computing_cell_refinement 'Bruker SMART V5.625' _computing_data_reduction 'Bruker SAINT V6.28A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL Rel. 6.12/V (Siemens, 1996)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0341P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _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 0.00(8) _refine_ls_number_reflns 3206 _refine_ls_number_parameters 198 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0833 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.004 _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 C1 C 0.75008(19) 0.3311(4) 0.85883(18) 0.0304(5) Uani 1 1 d . . . H1 H 0.7965 0.4653 0.8669 0.036 Uiso 1 1 calc R . . C2 C 0.78784(19) 0.1705(4) 0.79179(18) 0.0316(6) Uani 1 1 d . . . H2 H 0.7395 0.0507 0.7623 0.038 Uiso 1 1 calc R . . C3 C 0.88707(19) 0.1897(4) 0.77196(18) 0.0321(6) Uani 1 1 d . . . H3 H 0.9306 0.3167 0.7975 0.038 Uiso 1 1 calc R . . C4 C 0.93557(18) 0.0314(4) 0.71382(17) 0.0308(5) Uani 1 1 d . . . C5 C 0.8814(2) -0.1683(4) 0.67362(19) 0.0351(6) Uani 1 1 d . . . H5 H 0.8112 -0.2043 0.6823 0.042 Uiso 1 1 calc R . . C6 C 0.9305(2) -0.3146(4) 0.62080(19) 0.0399(6) Uani 1 1 d . . . H6 H 0.8926 -0.4462 0.5935 0.048 Uiso 1 1 calc R . . C7 C 1.0363(2) -0.2637(5) 0.6088(2) 0.0433(7) Uani 1 1 d . . . H7 H 1.0695 -0.3617 0.5738 0.052 Uiso 1 1 calc R . . C8 C 1.0918(2) -0.0679(5) 0.6488(2) 0.0447(7) Uani 1 1 d . . . H8 H 1.1627 -0.0341 0.6412 0.054 Uiso 1 1 calc R . . C9 C 1.0419(2) 0.0790(4) 0.70051(19) 0.0381(7) Uani 1 1 d . . . H9 H 1.0797 0.2112 0.7267 0.046 Uiso 1 1 calc R . . C10 C 0.7649(2) 0.2442(4) 0.97644(19) 0.0339(6) Uani 1 1 d . . . C11 C 0.6904(2) 0.0387(5) 0.9676(2) 0.0486(7) Uani 1 1 d . . . H11A H 0.6994 -0.0110 1.0400 0.073 Uiso 1 1 calc R . . H11B H 0.7159 -0.0742 0.9301 0.073 Uiso 1 1 calc R . . H11C H 0.6092 0.0722 0.9270 0.073 Uiso 1 1 calc R . . C12 C 0.8952(2) 0.1928(5) 1.0408(2) 0.0502(8) Uani 1 1 d . . . H12A H 0.9055 0.1509 1.1146 0.075 Uiso 1 1 calc R . . H12B H 0.9418 0.3205 1.0426 0.075 Uiso 1 1 calc R . . H12C H 0.9198 0.0749 1.0055 0.075 Uiso 1 1 calc R . . C13 C 0.7299(2) 0.4308(4) 1.03530(19) 0.0389(6) Uani 1 1 d . . . H13 H 0.7796 0.5518 1.0528 0.047 Uiso 1 1 calc R . . C14 C 0.6372(2) 0.4415(5) 1.0646(2) 0.0523(8) Uani 1 1 d . . . H14A H 0.5843 0.3253 1.0493 0.063 Uiso 1 1 calc R . . H14B H 0.6248 0.5652 1.1005 0.063 Uiso 1 1 calc R . . N1 N 0.62289(17) 0.3858(3) 0.80118(15) 0.0323(5) Uani 1 1 d . . . H1N H 0.601(2) 0.460(4) 0.8455(18) 0.039 Uiso 1 1 d . . . S1 S 0.58275(5) 0.50254(10) 0.67741(4) 0.03068(15) Uani 1 1 d . . . O1 O 0.60830(15) 0.7422(3) 0.68852(15) 0.0483(5) Uani 1 1 d . . . C15 C 0.42160(18) 0.4777(4) 0.64008(17) 0.0313(5) Uani 1 1 d . . . C16 C 0.3673(2) 0.6042(4) 0.5322(2) 0.0414(6) Uani 1 1 d . . . H16A H 0.2831 0.5951 0.5072 0.062 Uiso 1 1 calc R . . H16B H 0.3937 0.5420 0.4777 0.062 Uiso 1 1 calc R . . H16C H 0.3911 0.7550 0.5439 0.062 Uiso 1 1 calc R . . C17 C 0.3843(2) 0.5793(5) 0.7293(2) 0.0493(8) Uani 1 1 d . . . H17A H 0.4175 0.7234 0.7467 0.074 Uiso 1 1 calc R . . H17B H 0.4119 0.4895 0.7941 0.074 Uiso 1 1 calc R . . H17C H 0.3000 0.5889 0.7032 0.074 Uiso 1 1 calc R . . C18 C 0.3905(2) 0.2344(4) 0.6221(2) 0.0482(7) Uani 1 1 d . . . H18A H 0.4281 0.1561 0.6897 0.072 Uiso 1 1 calc R . . H18B H 0.4170 0.1775 0.5666 0.072 Uiso 1 1 calc R . . H18C H 0.3067 0.2168 0.5987 0.072 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 C1 0.0283(12) 0.0265(13) 0.0348(14) 0.0015(10) 0.0099(11) -0.0023(10) C2 0.0279(12) 0.0309(14) 0.0322(13) -0.0027(11) 0.0066(10) -0.0017(10) C3 0.0287(13) 0.0320(15) 0.0316(13) 0.0014(11) 0.0065(10) -0.0027(10) C4 0.0272(11) 0.0361(15) 0.0273(11) 0.0045(12) 0.0078(9) 0.0037(11) C5 0.0289(13) 0.0423(15) 0.0354(15) 0.0018(12) 0.0132(11) -0.0006(12) C6 0.0387(14) 0.0417(17) 0.0363(14) -0.0013(12) 0.0102(12) 0.0051(12) C7 0.0419(16) 0.0519(18) 0.0359(15) -0.0009(13) 0.0139(12) 0.0121(14) C8 0.0361(14) 0.057(2) 0.0455(16) 0.0057(13) 0.0198(13) 0.0059(13) C9 0.0332(13) 0.0443(18) 0.0362(14) 0.0039(11) 0.0120(12) -0.0031(11) C10 0.0331(13) 0.0332(14) 0.0317(14) 0.0004(11) 0.0074(11) 0.0018(11) C11 0.0660(17) 0.0355(17) 0.0471(15) 0.0074(13) 0.0239(13) -0.0026(14) C12 0.0460(16) 0.062(2) 0.0384(15) 0.0048(14) 0.0108(13) 0.0163(15) C13 0.0481(16) 0.0349(16) 0.0319(14) 0.0023(11) 0.0126(12) 0.0048(11) C14 0.0617(18) 0.055(2) 0.0452(16) 0.0045(14) 0.0252(14) 0.0159(15) N1 0.0284(10) 0.0408(13) 0.0259(11) 0.0020(9) 0.0076(9) 0.0051(9) S1 0.0295(3) 0.0332(3) 0.0288(3) 0.0006(3) 0.0100(2) -0.0026(3) O1 0.0459(11) 0.0342(10) 0.0545(12) 0.0045(9) 0.0059(9) -0.0127(8) C15 0.0296(11) 0.0300(14) 0.0328(12) 0.0000(12) 0.0095(9) -0.0037(12) C16 0.0387(14) 0.0422(16) 0.0362(14) 0.0047(12) 0.0053(12) 0.0000(12) C17 0.0378(14) 0.067(2) 0.0440(15) 0.0020(13) 0.0163(12) 0.0129(13) C18 0.0410(15) 0.0381(16) 0.0591(18) 0.0020(14) 0.0108(13) -0.0105(13) _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 C1 N1 1.495(3) . ? C1 C2 1.495(3) . ? C1 C10 1.571(3) . ? C1 H1 0.9800 . ? C2 C3 1.333(3) . ? C2 H2 0.9300 . ? C3 C4 1.480(3) . ? C3 H3 0.9300 . ? C4 C5 1.394(4) . ? C4 C9 1.402(3) . ? C5 C6 1.391(3) . ? C5 H5 0.9300 . ? C6 C7 1.392(3) . ? C6 H6 0.9300 . ? C7 C8 1.379(4) . ? C7 H7 0.9300 . ? C8 C9 1.389(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C13 1.520(3) . ? C10 C11 1.528(3) . ? C10 C12 1.536(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.322(3) . ? C13 H13 0.9300 . ? C14 H14A 0.9300 . ? C14 H14B 0.9300 . ? N1 S1 1.667(2) . ? N1 H1N 0.85(2) . ? S1 O1 1.4912(19) . ? S1 C15 1.852(2) . ? C15 C17 1.529(3) . ? C15 C16 1.529(3) . ? C15 C18 1.529(4) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 N1 C1 C2 109.73(19) . . ? N1 C1 C10 107.14(18) . . ? C2 C1 C10 113.64(19) . . ? N1 C1 H1 108.7 . . ? C2 C1 H1 108.7 . . ? C10 C1 H1 108.7 . . ? C3 C2 C1 123.5(2) . . ? C3 C2 H2 118.2 . . ? C1 C2 H2 118.2 . . ? C2 C3 C4 127.2(2) . . ? C2 C3 H3 116.4 . . ? C4 C3 H3 116.4 . . ? C5 C4 C9 117.9(2) . . ? C5 C4 C3 122.7(2) . . ? C9 C4 C3 119.4(2) . . ? C6 C5 C4 121.1(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 119.9(3) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 119.9(2) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 120.1(2) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C4 121.1(2) . . ? C8 C9 H9 119.4 . . ? C4 C9 H9 119.4 . . ? C13 C10 C11 112.6(2) . . ? C13 C10 C12 107.6(2) . . ? C11 C10 C12 110.0(2) . . ? C13 C10 C1 106.74(19) . . ? C11 C10 C1 110.5(2) . . ? C12 C10 C1 109.26(19) . . ? 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 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C10 127.7(3) . . ? C14 C13 H13 116.1 . . ? C10 C13 H13 116.1 . . ? C13 C14 H14A 120.0 . . ? C13 C14 H14B 120.0 . . ? H14A C14 H14B 120.0 . . ? C1 N1 S1 117.82(15) . . ? C1 N1 H1N 107.9(16) . . ? S1 N1 H1N 112.1(17) . . ? O1 S1 N1 110.35(11) . . ? O1 S1 C15 105.68(11) . . ? N1 S1 C15 97.34(10) . . ? C17 C15 C16 110.3(2) . . ? C17 C15 C18 112.6(2) . . ? C16 C15 C18 110.4(2) . . ? C17 C15 S1 110.49(16) . . ? C16 C15 S1 105.20(16) . . ? C18 C15 S1 107.48(17) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.157 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.032 _database_code_depnum_ccdc_archive 'CCDC 953178'