# 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_author_name 'Matthew OBrien' _publ_contact_author_email mo263@cam.ac.uk _publ_contact_author_name 'Matthew OBrien' data_sl0972 _database_code_depnum_ccdc_archive 'CCDC 856633' #TrackingRef '- sl0972.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H21 N O3 S' _chemical_formula_sum 'C17 H21 N O3 S' _chemical_formula_weight 319.41 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 P2(1)/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 19.0051(4) _cell_length_b 11.4052(2) _cell_length_c 15.9100(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.528(1) _cell_angle_gamma 90.00 _cell_volume 3250.23(11) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 35045 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.211 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.917 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 37289 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 27.87 _reflns_number_total 7717 _reflns_number_gt 5036 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-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^)+(0.0388P)^2^+1.7268P] 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 7717 _refine_ls_number_parameters 401 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0955 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1166 _refine_ls_wR_factor_gt 0.1013 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.022 _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 S1_1 S 0.49167(3) 0.80454(5) 0.24090(3) 0.03340(14) Uani 1 1 d . . . C1_1 C 0.27828(14) 0.9481(2) 0.34360(17) 0.0489(6) Uani 1 1 d . . . H1_1 H 0.2314 0.9702 0.3018 0.059 Uiso 1 1 calc R . . N1_1 N 0.46295(9) 0.77335(14) 0.32366(10) 0.0292(4) Uani 1 1 d . . . O1_1 O 0.34069(8) 0.92158(14) 0.32223(10) 0.0447(4) Uani 1 1 d . . . C2_1 C 0.29255(13) 0.9385(2) 0.43068(16) 0.0458(6) Uani 1 1 d . . . H2_1 H 0.2587 0.9530 0.4619 0.055 Uiso 1 1 calc R . . O2_1 O 0.46831(8) 0.92202(14) 0.21359(10) 0.0441(4) Uani 1 1 d . . . C3_1 C 0.36858(13) 0.9022(2) 0.46863(15) 0.0399(5) Uani 1 1 d . . . H3_1 H 0.3951 0.8879 0.5299 0.048 Uiso 1 1 calc R . . O3_1 O 0.46859(8) 0.71078(14) 0.17791(9) 0.0435(4) Uani 1 1 d . . . C4_1 C 0.39527(12) 0.89229(17) 0.40068(13) 0.0325(5) Uani 1 1 d . . . C5_1 C 0.47003(11) 0.86414(17) 0.39326(13) 0.0318(5) Uani 1 1 d . . . H5_1 H 0.4888 0.9372 0.3731 0.038 Uiso 1 1 calc R . . C6_1 C 0.52764(12) 0.82915(19) 0.48282(13) 0.0359(5) Uani 1 1 d . . . H6A_1 H 0.5783 0.8400 0.4795 0.043 Uiso 1 1 calc R . . H6B_1 H 0.5226 0.8822 0.5298 0.043 Uiso 1 1 calc R . . C7_1 C 0.51950(12) 0.70274(19) 0.50941(13) 0.0369(5) Uani 1 1 d . . . H7A_1 H 0.5601 0.6834 0.5655 0.044 Uiso 1 1 calc R . . H7B_1 H 0.4712 0.6927 0.5195 0.044 Uiso 1 1 calc R . . C8_1 C 0.52307(13) 0.62165(19) 0.43564(13) 0.0373(5) Uani 1 1 d . . . H8A_1 H 0.5188 0.5394 0.4532 0.045 Uiso 1 1 calc R . . H8B_1 H 0.5720 0.6308 0.4270 0.045 Uiso 1 1 calc R . . C9_1 C 0.46108(12) 0.64762(17) 0.34838(13) 0.0329(5) Uani 1 1 d . . . H9_1 H 0.4713 0.5999 0.3010 0.040 Uiso 1 1 calc R . . C10_1 C 0.38345(13) 0.6146(2) 0.34819(16) 0.0448(6) Uani 1 1 d . . . H10A_1 H 0.3465 0.6355 0.2906 0.067 Uiso 1 1 calc R . . H10B_1 H 0.3725 0.6570 0.3960 0.067 Uiso 1 1 calc R . . H10C_1 H 0.3814 0.5300 0.3579 0.067 Uiso 1 1 calc R . . C11_1 C 0.59021(11) 0.80493(19) 0.28274(13) 0.0336(5) Uani 1 1 d . . . C12_1 C 0.62758(12) 0.9069(2) 0.31985(14) 0.0394(5) Uani 1 1 d . . . H12_1 H 0.6007 0.9776 0.3183 0.047 Uiso 1 1 calc R . . C13_1 C 0.70435(13) 0.9048(2) 0.35916(15) 0.0481(6) Uani 1 1 d . . . H13_1 H 0.7299 0.9749 0.3840 0.058 Uiso 1 1 calc R . . C14_1 C 0.74495(13) 0.8027(3) 0.36319(16) 0.0535(7) Uani 1 1 d . . . C15_1 C 0.70659(14) 0.7023(3) 0.32483(18) 0.0556(7) Uani 1 1 d . . . H15_1 H 0.7336 0.6318 0.3263 0.067 Uiso 1 1 calc R . . C16_1 C 0.62967(13) 0.7024(2) 0.28427(16) 0.0445(6) Uani 1 1 d . . . H16_1 H 0.6043 0.6329 0.2578 0.053 Uiso 1 1 calc R . . C17_1 C 0.82863(14) 0.8016(3) 0.4097(2) 0.0801(10) Uani 1 1 d . . . H17A_1 H 0.8488 0.7254 0.4004 0.120 Uiso 1 1 calc R . . H17B_1 H 0.8397 0.8148 0.4737 0.120 Uiso 1 1 calc R . . H17C_1 H 0.8516 0.8638 0.3851 0.120 Uiso 1 1 calc R . . S1_2 S 0.05603(3) 0.90780(5) 0.22920(4) 0.03894(15) Uani 1 1 d . . . C1_2 C 0.28124(13) 0.8816(2) 0.11129(16) 0.0482(6) Uani 1 1 d . . . H1_2 H 0.3294 0.9110 0.1440 0.058 Uiso 1 1 calc R . . N1_2 N 0.09074(9) 0.81738(15) 0.17375(11) 0.0356(4) Uani 1 1 d . . . O1_2 O 0.21832(8) 0.89898(14) 0.13373(10) 0.0416(4) Uani 1 1 d . . . C2_2 C 0.26543(14) 0.8177(2) 0.03726(16) 0.0499(6) Uani 1 1 d . . . H2_2 H 0.2993 0.7942 0.0080 0.060 Uiso 1 1 calc R . . O2_2 O 0.06854(9) 1.02391(13) 0.20301(12) 0.0502(4) Uani 1 1 d . . . C3_2 C 0.18768(14) 0.7913(2) 0.01034(15) 0.0455(6) Uani 1 1 d . . . H3_2 H 0.1597 0.7471 -0.0405 0.055 Uiso 1 1 calc R . . O3_2 O 0.08489(9) 0.87427(16) 0.32071(10) 0.0515(4) Uani 1 1 d . . . C4_2 C 0.16152(12) 0.84103(19) 0.07072(14) 0.0357(5) Uani 1 1 d . . . C5_2 C 0.08653(12) 0.84954(19) 0.08155(14) 0.0362(5) Uani 1 1 d . . . H5_2 H 0.0704 0.9333 0.0719 0.043 Uiso 1 1 calc R . . C6_2 C 0.02806(13) 0.7762(2) 0.01208(15) 0.0457(6) Uani 1 1 d . . . H6A_2 H -0.0224 0.8001 0.0107 0.055 Uiso 1 1 calc R . . H6B_2 H 0.0317 0.7915 -0.0476 0.055 Uiso 1 1 calc R . . C7_2 C 0.03823(16) 0.6454(2) 0.03210(17) 0.0556(7) Uani 1 1 d . . . H7A_2 H -0.0022 0.6012 -0.0123 0.067 Uiso 1 1 calc R . . H7B_2 H 0.0865 0.6193 0.0274 0.067 Uiso 1 1 calc R . . C8_2 C 0.03676(16) 0.6199(2) 0.12503(17) 0.0547(7) Uani 1 1 d . . . H8A_2 H 0.0460 0.5352 0.1377 0.066 Uiso 1 1 calc R . . H8B_2 H -0.0136 0.6381 0.1271 0.066 Uiso 1 1 calc R . . C9_2 C 0.09497(14) 0.6906(2) 0.19779(16) 0.0454(6) Uani 1 1 d . . . H9_2 H 0.0817 0.6838 0.2533 0.054 Uiso 1 1 calc R . . C10_2 C 0.17463(15) 0.6463(2) 0.22007(18) 0.0587(7) Uani 1 1 d . . . H10A_2 H 0.2081 0.6944 0.2678 0.088 Uiso 1 1 calc R . . H10B_2 H 0.1897 0.6516 0.1670 0.088 Uiso 1 1 calc R . . H10C_2 H 0.1774 0.5645 0.2398 0.088 Uiso 1 1 calc R . . C11_2 C -0.04153(12) 0.88476(18) 0.19294(14) 0.0355(5) Uani 1 1 d . . . C12_2 C -0.08837(13) 0.9517(2) 0.12474(15) 0.0428(5) Uani 1 1 d . . . H12_2 H -0.0688 1.0142 0.0998 0.051 Uiso 1 1 calc R . . C13_2 C -0.16382(13) 0.9273(2) 0.09298(16) 0.0496(6) Uani 1 1 d . . . H13_2 H -0.1959 0.9743 0.0466 0.060 Uiso 1 1 calc R . . C14_2 C -0.19383(13) 0.8357(2) 0.12723(16) 0.0451(6) Uani 1 1 d . . . C15_2 C -0.14583(13) 0.7693(2) 0.19528(16) 0.0469(6) Uani 1 1 d . . . H15_2 H -0.1653 0.7057 0.2193 0.056 Uiso 1 1 calc R . . C16_2 C -0.07086(13) 0.7932(2) 0.22883(15) 0.0446(6) Uani 1 1 d . . . H16_2 H -0.0391 0.7475 0.2763 0.053 Uiso 1 1 calc R . . C17_2 C -0.27638(14) 0.8091(3) 0.0915(2) 0.0672(8) Uani 1 1 d . . . H17A_2 H -0.2967 0.8105 0.1405 0.101 Uiso 1 1 calc R . . H17B_2 H -0.2842 0.7313 0.0637 0.101 Uiso 1 1 calc R . . H17C_2 H -0.3018 0.8682 0.0470 0.101 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 S1_1 0.0348(3) 0.0402(3) 0.0255(2) 0.0061(2) 0.0106(2) -0.0039(2) C1_1 0.0442(14) 0.0537(16) 0.0507(15) 0.0032(12) 0.0182(11) 0.0134(12) N1_1 0.0371(9) 0.0253(9) 0.0280(8) 0.0002(7) 0.0148(7) -0.0037(7) O1_1 0.0448(9) 0.0550(10) 0.0356(8) 0.0052(7) 0.0150(7) 0.0117(8) C2_1 0.0492(14) 0.0438(14) 0.0509(14) -0.0055(11) 0.0254(12) 0.0030(11) O2_1 0.0411(9) 0.0465(10) 0.0439(9) 0.0208(7) 0.0131(7) 0.0006(7) C3_1 0.0500(13) 0.0368(12) 0.0347(11) -0.0057(10) 0.0166(10) -0.0030(11) O3_1 0.0492(9) 0.0572(11) 0.0251(7) -0.0063(7) 0.0135(6) -0.0137(8) C4_1 0.0414(12) 0.0228(11) 0.0323(11) -0.0019(8) 0.0111(9) -0.0012(9) C5_1 0.0413(12) 0.0226(10) 0.0328(11) -0.0013(8) 0.0140(9) -0.0050(9) C6_1 0.0403(12) 0.0343(12) 0.0323(11) -0.0060(9) 0.0112(9) -0.0038(10) C7_1 0.0459(12) 0.0392(13) 0.0264(10) 0.0021(9) 0.0133(9) 0.0032(10) C8_1 0.0544(14) 0.0294(12) 0.0335(11) 0.0057(9) 0.0222(10) 0.0028(10) C9_1 0.0473(13) 0.0252(11) 0.0321(11) -0.0033(8) 0.0210(10) -0.0050(9) C10_1 0.0554(14) 0.0356(13) 0.0523(14) -0.0112(11) 0.0297(12) -0.0164(11) C11_1 0.0366(11) 0.0395(12) 0.0275(10) 0.0068(9) 0.0144(9) -0.0034(10) C12_1 0.0410(12) 0.0436(13) 0.0349(11) 0.0063(10) 0.0143(10) -0.0040(11) C13_1 0.0453(14) 0.0614(17) 0.0368(12) 0.0054(12) 0.0123(10) -0.0146(13) C14_1 0.0387(13) 0.080(2) 0.0418(13) 0.0187(14) 0.0137(10) -0.0012(14) C15_1 0.0480(15) 0.0612(18) 0.0640(16) 0.0187(14) 0.0272(13) 0.0123(14) C16_1 0.0449(13) 0.0435(14) 0.0517(14) 0.0035(11) 0.0250(11) -0.0004(11) C17_1 0.0375(14) 0.130(3) 0.0681(19) 0.029(2) 0.0111(13) 0.0007(17) S1_2 0.0380(3) 0.0355(3) 0.0415(3) -0.0081(2) 0.0110(2) -0.0002(2) C1_2 0.0330(12) 0.0592(17) 0.0521(15) 0.0019(12) 0.0138(11) 0.0040(11) N1_2 0.0387(10) 0.0314(10) 0.0376(10) -0.0012(8) 0.0140(8) 0.0018(8) O1_2 0.0339(8) 0.0481(10) 0.0408(8) -0.0085(7) 0.0101(7) -0.0012(7) C2_2 0.0518(15) 0.0533(16) 0.0509(15) 0.0037(12) 0.0255(12) 0.0119(12) O2_2 0.0518(10) 0.0310(9) 0.0701(11) -0.0137(8) 0.0235(8) -0.0071(7) C3_2 0.0554(15) 0.0407(14) 0.0406(13) -0.0044(11) 0.0163(11) 0.0012(12) O3_2 0.0448(9) 0.0668(12) 0.0372(9) -0.0095(8) 0.0062(7) 0.0066(8) C4_2 0.0401(12) 0.0305(11) 0.0331(11) -0.0005(9) 0.0077(9) 0.0008(10) C5_2 0.0395(12) 0.0304(12) 0.0354(11) 0.0001(9) 0.0081(9) 0.0005(9) C6_2 0.0464(13) 0.0438(14) 0.0409(13) -0.0063(11) 0.0064(10) -0.0085(11) C7_2 0.0721(18) 0.0381(14) 0.0553(16) -0.0131(12) 0.0198(13) -0.0166(13) C8_2 0.0737(18) 0.0338(14) 0.0614(16) -0.0052(12) 0.0286(14) -0.0108(12) C9_2 0.0608(15) 0.0318(12) 0.0485(13) 0.0068(10) 0.0249(12) 0.0066(11) C10_2 0.0722(18) 0.0475(16) 0.0595(16) 0.0147(13) 0.0261(14) 0.0244(14) C11_2 0.0396(12) 0.0305(12) 0.0373(12) -0.0024(9) 0.0140(9) 0.0040(9) C12_2 0.0455(13) 0.0354(13) 0.0485(13) 0.0084(10) 0.0171(11) 0.0048(10) C13_2 0.0456(14) 0.0511(16) 0.0499(14) 0.0136(12) 0.0128(11) 0.0125(12) C14_2 0.0401(13) 0.0460(15) 0.0490(14) 0.0003(11) 0.0147(11) 0.0056(11) C15_2 0.0439(13) 0.0432(14) 0.0554(14) 0.0085(12) 0.0192(11) -0.0006(11) C16_2 0.0466(13) 0.0429(14) 0.0433(13) 0.0116(11) 0.0138(10) 0.0053(11) C17_2 0.0411(14) 0.074(2) 0.079(2) 0.0064(16) 0.0102(13) -0.0001(14) _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 S1_1 O3_1 1.4305(16) . ? S1_1 O2_1 1.4325(16) . ? S1_1 N1_1 1.6245(16) . ? S1_1 C11_1 1.765(2) . ? C1_1 C2_1 1.324(3) . ? C1_1 O1_1 1.372(3) . ? C1_1 H1_1 0.9500 . ? N1_1 C5_1 1.489(2) . ? N1_1 C9_1 1.491(3) . ? O1_1 C4_1 1.371(2) . ? C2_1 C3_1 1.429(3) . ? C2_1 H2_1 0.9500 . ? C3_1 C4_1 1.344(3) . ? C3_1 H3_1 0.9500 . ? C4_1 C5_1 1.499(3) . ? C5_1 C6_1 1.531(3) . ? C5_1 H5_1 1.0000 . ? C6_1 C7_1 1.525(3) . ? C6_1 H6A_1 0.9900 . ? C6_1 H6B_1 0.9900 . ? C7_1 C8_1 1.514(3) . ? C7_1 H7A_1 0.9900 . ? C7_1 H7B_1 0.9900 . ? C8_1 C9_1 1.520(3) . ? C8_1 H8A_1 0.9900 . ? C8_1 H8B_1 0.9900 . ? C9_1 C10_1 1.522(3) . ? C9_1 H9_1 1.0000 . ? C10_1 H10A_1 0.9800 . ? C10_1 H10B_1 0.9800 . ? C10_1 H10C_1 0.9800 . ? C11_1 C16_1 1.385(3) . ? C11_1 C12_1 1.388(3) . ? C12_1 C13_1 1.382(3) . ? C12_1 H12_1 0.9500 . ? C13_1 C14_1 1.386(4) . ? C13_1 H13_1 0.9500 . ? C14_1 C15_1 1.384(4) . ? C14_1 C17_1 1.513(3) . ? C15_1 C16_1 1.387(3) . ? C15_1 H15_1 0.9500 . ? C16_1 H16_1 0.9500 . ? C17_1 H17A_1 0.9800 . ? C17_1 H17B_1 0.9800 . ? C17_1 H17C_1 0.9800 . ? S1_2 O3_2 1.4257(17) . ? S1_2 O2_2 1.4318(17) . ? S1_2 N1_2 1.6328(18) . ? S1_2 C11_2 1.768(2) . ? C1_2 C2_2 1.331(3) . ? C1_2 O1_2 1.372(3) . ? C1_2 H1_2 0.9500 . ? N1_2 C5_2 1.488(3) . ? N1_2 C9_2 1.491(3) . ? O1_2 C4_2 1.372(2) . ? C2_2 C3_2 1.426(3) . ? C2_2 H2_2 0.9500 . ? C3_2 C4_2 1.346(3) . ? C3_2 H3_2 0.9500 . ? C4_2 C5_2 1.495(3) . ? C5_2 C6_2 1.528(3) . ? C5_2 H5_2 1.0000 . ? C6_2 C7_2 1.524(3) . ? C6_2 H6A_2 0.9900 . ? C6_2 H6B_2 0.9900 . ? C7_2 C8_2 1.516(4) . ? C7_2 H7A_2 0.9900 . ? C7_2 H7B_2 0.9900 . ? C8_2 C9_2 1.535(3) . ? C8_2 H8A_2 0.9900 . ? C8_2 H8B_2 0.9900 . ? C9_2 C10_2 1.521(3) . ? C9_2 H9_2 1.0000 . ? C10_2 H10A_2 0.9800 . ? C10_2 H10B_2 0.9800 . ? C10_2 H10C_2 0.9800 . ? C11_2 C12_2 1.381(3) . ? C11_2 C16_2 1.393(3) . ? C12_2 C13_2 1.380(3) . ? C12_2 H12_2 0.9500 . ? C13_2 C14_2 1.386(3) . ? C13_2 H13_2 0.9500 . ? C14_2 C15_2 1.385(3) . ? C14_2 C17_2 1.510(3) . ? C15_2 C16_2 1.371(3) . ? C15_2 H15_2 0.9500 . ? C16_2 H16_2 0.9500 . ? C17_2 H17A_2 0.9800 . ? C17_2 H17B_2 0.9800 . ? C17_2 H17C_2 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 O3_1 S1_1 O2_1 119.70(10) . . ? O3_1 S1_1 N1_1 107.26(9) . . ? O2_1 S1_1 N1_1 107.25(9) . . ? O3_1 S1_1 C11_1 107.71(10) . . ? O2_1 S1_1 C11_1 107.11(10) . . ? N1_1 S1_1 C11_1 107.24(9) . . ? C2_1 C1_1 O1_1 110.5(2) . . ? C2_1 C1_1 H1_1 124.8 . . ? O1_1 C1_1 H1_1 124.8 . . ? C5_1 N1_1 C9_1 118.49(15) . . ? C5_1 N1_1 S1_1 118.63(13) . . ? C9_1 N1_1 S1_1 117.95(13) . . ? C4_1 O1_1 C1_1 106.35(17) . . ? C1_1 C2_1 C3_1 106.9(2) . . ? C1_1 C2_1 H2_1 126.6 . . ? C3_1 C2_1 H2_1 126.6 . . ? C4_1 C3_1 C2_1 106.6(2) . . ? C4_1 C3_1 H3_1 126.7 . . ? C2_1 C3_1 H3_1 126.7 . . ? C3_1 C4_1 O1_1 109.74(19) . . ? C3_1 C4_1 C5_1 134.75(19) . . ? O1_1 C4_1 C5_1 115.40(17) . . ? N1_1 C5_1 C4_1 110.80(16) . . ? N1_1 C5_1 C6_1 111.69(16) . . ? C4_1 C5_1 C6_1 112.58(17) . . ? N1_1 C5_1 H5_1 107.1 . . ? C4_1 C5_1 H5_1 107.1 . . ? C6_1 C5_1 H5_1 107.1 . . ? C7_1 C6_1 C5_1 113.41(17) . . ? C7_1 C6_1 H6A_1 108.9 . . ? C5_1 C6_1 H6A_1 108.9 . . ? C7_1 C6_1 H6B_1 108.9 . . ? C5_1 C6_1 H6B_1 108.9 . . ? H6A_1 C6_1 H6B_1 107.7 . . ? C8_1 C7_1 C6_1 109.12(17) . . ? C8_1 C7_1 H7A_1 109.9 . . ? C6_1 C7_1 H7A_1 109.9 . . ? C8_1 C7_1 H7B_1 109.9 . . ? C6_1 C7_1 H7B_1 109.9 . . ? H7A_1 C7_1 H7B_1 108.3 . . ? C7_1 C8_1 C9_1 111.55(18) . . ? C7_1 C8_1 H8A_1 109.3 . . ? C9_1 C8_1 H8A_1 109.3 . . ? C7_1 C8_1 H8B_1 109.3 . . ? C9_1 C8_1 H8B_1 109.3 . . ? H8A_1 C8_1 H8B_1 108.0 . . ? N1_1 C9_1 C8_1 110.42(16) . . ? N1_1 C9_1 C10_1 110.26(17) . . ? C8_1 C9_1 C10_1 114.11(18) . . ? N1_1 C9_1 H9_1 107.2 . . ? C8_1 C9_1 H9_1 107.2 . . ? C10_1 C9_1 H9_1 107.2 . . ? C9_1 C10_1 H10A_1 109.5 . . ? C9_1 C10_1 H10B_1 109.5 . . ? H10A_1 C10_1 H10B_1 109.5 . . ? C9_1 C10_1 H10C_1 109.5 . . ? H10A_1 C10_1 H10C_1 109.5 . . ? H10B_1 C10_1 H10C_1 109.5 . . ? C16_1 C11_1 C12_1 120.2(2) . . ? C16_1 C11_1 S1_1 120.30(17) . . ? C12_1 C11_1 S1_1 119.34(17) . . ? C13_1 C12_1 C11_1 119.4(2) . . ? C13_1 C12_1 H12_1 120.3 . . ? C11_1 C12_1 H12_1 120.3 . . ? C12_1 C13_1 C14_1 121.5(2) . . ? C12_1 C13_1 H13_1 119.2 . . ? C14_1 C13_1 H13_1 119.2 . . ? C15_1 C14_1 C13_1 118.1(2) . . ? C15_1 C14_1 C17_1 121.4(3) . . ? C13_1 C14_1 C17_1 120.5(3) . . ? C14_1 C15_1 C16_1 121.5(2) . . ? C14_1 C15_1 H15_1 119.3 . . ? C16_1 C15_1 H15_1 119.3 . . ? C11_1 C16_1 C15_1 119.3(2) . . ? C11_1 C16_1 H16_1 120.3 . . ? C15_1 C16_1 H16_1 120.3 . . ? C14_1 C17_1 H17A_1 109.5 . . ? C14_1 C17_1 H17B_1 109.5 . . ? H17A_1 C17_1 H17B_1 109.5 . . ? C14_1 C17_1 H17C_1 109.5 . . ? H17A_1 C17_1 H17C_1 109.5 . . ? H17B_1 C17_1 H17C_1 109.5 . . ? O3_2 S1_2 O2_2 120.05(11) . . ? O3_2 S1_2 N1_2 107.18(10) . . ? O2_2 S1_2 N1_2 106.89(10) . . ? O3_2 S1_2 C11_2 107.27(10) . . ? O2_2 S1_2 C11_2 107.49(10) . . ? N1_2 S1_2 C11_2 107.39(10) . . ? C2_2 C1_2 O1_2 110.5(2) . . ? C2_2 C1_2 H1_2 124.7 . . ? O1_2 C1_2 H1_2 124.7 . . ? C5_2 N1_2 C9_2 118.19(17) . . ? C5_2 N1_2 S1_2 118.60(14) . . ? C9_2 N1_2 S1_2 118.09(14) . . ? C1_2 O1_2 C4_2 106.34(17) . . ? C1_2 C2_2 C3_2 106.6(2) . . ? C1_2 C2_2 H2_2 126.7 . . ? C3_2 C2_2 H2_2 126.7 . . ? C4_2 C3_2 C2_2 106.8(2) . . ? C4_2 C3_2 H3_2 126.6 . . ? C2_2 C3_2 H3_2 126.6 . . ? C3_2 C4_2 O1_2 109.66(19) . . ? C3_2 C4_2 C5_2 134.7(2) . . ? O1_2 C4_2 C5_2 115.58(18) . . ? N1_2 C5_2 C4_2 111.01(17) . . ? N1_2 C5_2 C6_2 111.37(18) . . ? C4_2 C5_2 C6_2 111.82(18) . . ? N1_2 C5_2 H5_2 107.5 . . ? C4_2 C5_2 H5_2 107.5 . . ? C6_2 C5_2 H5_2 107.5 . . ? C7_2 C6_2 C5_2 111.96(19) . . ? C7_2 C6_2 H6A_2 109.2 . . ? C5_2 C6_2 H6A_2 109.2 . . ? C7_2 C6_2 H6B_2 109.2 . . ? C5_2 C6_2 H6B_2 109.2 . . ? H6A_2 C6_2 H6B_2 107.9 . . ? C8_2 C7_2 C6_2 110.4(2) . . ? C8_2 C7_2 H7A_2 109.6 . . ? C6_2 C7_2 H7A_2 109.6 . . ? C8_2 C7_2 H7B_2 109.6 . . ? C6_2 C7_2 H7B_2 109.6 . . ? H7A_2 C7_2 H7B_2 108.1 . . ? C7_2 C8_2 C9_2 113.0(2) . . ? C7_2 C8_2 H8A_2 109.0 . . ? C9_2 C8_2 H8A_2 109.0 . . ? C7_2 C8_2 H8B_2 109.0 . . ? C9_2 C8_2 H8B_2 109.0 . . ? H8A_2 C8_2 H8B_2 107.8 . . ? N1_2 C9_2 C10_2 110.2(2) . . ? N1_2 C9_2 C8_2 110.63(19) . . ? C10_2 C9_2 C8_2 114.3(2) . . ? N1_2 C9_2 H9_2 107.1 . . ? C10_2 C9_2 H9_2 107.1 . . ? C8_2 C9_2 H9_2 107.1 . . ? C9_2 C10_2 H10A_2 109.5 . . ? C9_2 C10_2 H10B_2 109.5 . . ? H10A_2 C10_2 H10B_2 109.5 . . ? C9_2 C10_2 H10C_2 109.5 . . ? H10A_2 C10_2 H10C_2 109.5 . . ? H10B_2 C10_2 H10C_2 109.5 . . ? C12_2 C11_2 C16_2 119.7(2) . . ? C12_2 C11_2 S1_2 120.31(17) . . ? C16_2 C11_2 S1_2 119.83(17) . . ? C13_2 C12_2 C11_2 119.6(2) . . ? C13_2 C12_2 H12_2 120.2 . . ? C11_2 C12_2 H12_2 120.2 . . ? C12_2 C13_2 C14_2 121.4(2) . . ? C12_2 C13_2 H13_2 119.3 . . ? C14_2 C13_2 H13_2 119.3 . . ? C15_2 C14_2 C13_2 118.0(2) . . ? C15_2 C14_2 C17_2 120.9(2) . . ? C13_2 C14_2 C17_2 121.0(2) . . ? C16_2 C15_2 C14_2 121.5(2) . . ? C16_2 C15_2 H15_2 119.3 . . ? C14_2 C15_2 H15_2 119.3 . . ? C15_2 C16_2 C11_2 119.7(2) . . ? C15_2 C16_2 H16_2 120.1 . . ? C11_2 C16_2 H16_2 120.1 . . ? C14_2 C17_2 H17A_2 109.5 . . ? C14_2 C17_2 H17B_2 109.5 . . ? H17A_2 C17_2 H17B_2 109.5 . . ? C14_2 C17_2 H17C_2 109.5 . . ? H17A_2 C17_2 H17C_2 109.5 . . ? H17B_2 C17_2 H17C_2 109.5 . . ? 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 O3_1 S1_1 N1_1 C5_1 -171.53(14) . . . . ? O2_1 S1_1 N1_1 C5_1 -41.76(16) . . . . ? C11_1 S1_1 N1_1 C5_1 73.00(16) . . . . ? O3_1 S1_1 N1_1 C9_1 33.66(17) . . . . ? O2_1 S1_1 N1_1 C9_1 163.42(14) . . . . ? C11_1 S1_1 N1_1 C9_1 -81.81(16) . . . . ? C2_1 C1_1 O1_1 C4_1 1.1(3) . . . . ? O1_1 C1_1 C2_1 C3_1 -0.7(3) . . . . ? C1_1 C2_1 C3_1 C4_1 0.0(3) . . . . ? C2_1 C3_1 C4_1 O1_1 0.7(2) . . . . ? C2_1 C3_1 C4_1 C5_1 176.5(2) . . . . ? C1_1 O1_1 C4_1 C3_1 -1.1(2) . . . . ? C1_1 O1_1 C4_1 C5_1 -177.82(18) . . . . ? C9_1 N1_1 C5_1 C4_1 -83.6(2) . . . . ? S1_1 N1_1 C5_1 C4_1 121.68(16) . . . . ? C9_1 N1_1 C5_1 C6_1 42.7(2) . . . . ? S1_1 N1_1 C5_1 C6_1 -111.94(17) . . . . ? C3_1 C4_1 C5_1 N1_1 131.8(2) . . . . ? O1_1 C4_1 C5_1 N1_1 -52.6(2) . . . . ? C3_1 C4_1 C5_1 C6_1 5.9(3) . . . . ? O1_1 C4_1 C5_1 C6_1 -178.50(17) . . . . ? N1_1 C5_1 C6_1 C7_1 -46.2(2) . . . . ? C4_1 C5_1 C6_1 C7_1 79.2(2) . . . . ? C5_1 C6_1 C7_1 C8_1 55.7(2) . . . . ? C6_1 C7_1 C8_1 C9_1 -60.1(2) . . . . ? C5_1 N1_1 C9_1 C8_1 -47.1(2) . . . . ? S1_1 N1_1 C9_1 C8_1 107.70(16) . . . . ? C5_1 N1_1 C9_1 C10_1 79.9(2) . . . . ? S1_1 N1_1 C9_1 C10_1 -125.28(16) . . . . ? C7_1 C8_1 C9_1 N1_1 55.0(2) . . . . ? C7_1 C8_1 C9_1 C10_1 -69.9(2) . . . . ? O3_1 S1_1 C11_1 C16_1 -26.68(19) . . . . ? O2_1 S1_1 C11_1 C16_1 -156.66(17) . . . . ? N1_1 S1_1 C11_1 C16_1 88.48(18) . . . . ? O3_1 S1_1 C11_1 C12_1 157.84(16) . . . . ? O2_1 S1_1 C11_1 C12_1 27.87(18) . . . . ? N1_1 S1_1 C11_1 C12_1 -86.99(17) . . . . ? C16_1 C11_1 C12_1 C13_1 -0.7(3) . . . . ? S1_1 C11_1 C12_1 C13_1 174.75(16) . . . . ? C11_1 C12_1 C13_1 C14_1 -0.6(3) . . . . ? C12_1 C13_1 C14_1 C15_1 1.4(3) . . . . ? C12_1 C13_1 C14_1 C17_1 -177.6(2) . . . . ? C13_1 C14_1 C15_1 C16_1 -0.7(4) . . . . ? C17_1 C14_1 C15_1 C16_1 178.2(2) . . . . ? C12_1 C11_1 C16_1 C15_1 1.3(3) . . . . ? S1_1 C11_1 C16_1 C15_1 -174.11(17) . . . . ? C14_1 C15_1 C16_1 C11_1 -0.6(3) . . . . ? O3_2 S1_2 N1_2 C5_2 -164.14(15) . . . . ? O2_2 S1_2 N1_2 C5_2 -34.24(17) . . . . ? C11_2 S1_2 N1_2 C5_2 80.87(17) . . . . ? O3_2 S1_2 N1_2 C9_2 41.58(18) . . . . ? O2_2 S1_2 N1_2 C9_2 171.49(16) . . . . ? C11_2 S1_2 N1_2 C9_2 -73.41(18) . . . . ? C2_2 C1_2 O1_2 C4_2 1.0(3) . . . . ? O1_2 C1_2 C2_2 C3_2 -0.4(3) . . . . ? C1_2 C2_2 C3_2 C4_2 -0.3(3) . . . . ? C2_2 C3_2 C4_2 O1_2 0.9(3) . . . . ? C2_2 C3_2 C4_2 C5_2 178.5(2) . . . . ? C1_2 O1_2 C4_2 C3_2 -1.1(2) . . . . ? C1_2 O1_2 C4_2 C5_2 -179.27(18) . . . . ? C9_2 N1_2 C5_2 C4_2 -77.8(2) . . . . ? S1_2 N1_2 C5_2 C4_2 128.00(16) . . . . ? C9_2 N1_2 C5_2 C6_2 47.6(2) . . . . ? S1_2 N1_2 C5_2 C6_2 -106.69(19) . . . . ? C3_2 C4_2 C5_2 N1_2 131.2(3) . . . . ? O1_2 C4_2 C5_2 N1_2 -51.3(2) . . . . ? C3_2 C4_2 C5_2 C6_2 6.1(4) . . . . ? O1_2 C4_2 C5_2 C6_2 -176.37(18) . . . . ? N1_2 C5_2 C6_2 C7_2 -50.9(3) . . . . ? C4_2 C5_2 C6_2 C7_2 74.0(2) . . . . ? C5_2 C6_2 C7_2 C8_2 56.1(3) . . . . ? C6_2 C7_2 C8_2 C9_2 -55.9(3) . . . . ? C5_2 N1_2 C9_2 C10_2 80.9(2) . . . . ? S1_2 N1_2 C9_2 C10_2 -124.70(18) . . . . ? C5_2 N1_2 C9_2 C8_2 -46.5(3) . . . . ? S1_2 N1_2 C9_2 C8_2 107.90(19) . . . . ? C7_2 C8_2 C9_2 N1_2 49.7(3) . . . . ? C7_2 C8_2 C9_2 C10_2 -75.4(3) . . . . ? O3_2 S1_2 C11_2 C12_2 151.97(18) . . . . ? O2_2 S1_2 C11_2 C12_2 21.6(2) . . . . ? N1_2 S1_2 C11_2 C12_2 -93.10(19) . . . . ? O3_2 S1_2 C11_2 C16_2 -32.7(2) . . . . ? O2_2 S1_2 C11_2 C16_2 -163.03(18) . . . . ? N1_2 S1_2 C11_2 C16_2 82.3(2) . . . . ? C16_2 C11_2 C12_2 C13_2 0.1(3) . . . . ? S1_2 C11_2 C12_2 C13_2 175.52(18) . . . . ? C11_2 C12_2 C13_2 C14_2 -0.9(4) . . . . ? C12_2 C13_2 C14_2 C15_2 0.5(4) . . . . ? C12_2 C13_2 C14_2 C17_2 -179.4(2) . . . . ? C13_2 C14_2 C15_2 C16_2 0.6(4) . . . . ? C17_2 C14_2 C15_2 C16_2 -179.5(2) . . . . ? C14_2 C15_2 C16_2 C11_2 -1.3(4) . . . . ? C12_2 C11_2 C16_2 C15_2 0.9(3) . . . . ? S1_2 C11_2 C16_2 C15_2 -174.48(18) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.298 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.048