# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/229 # Note that no CIF is available for structure 1a (form 3) data_231696 _audit_creation_method SHELXL _audit_update_record ; ? ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H27 N O2 S' _chemical_formula_weight 321.47 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.392(2) _cell_length_b 10.962(2) _cell_length_c 17.823(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.29(3) _cell_angle_gamma 90.00 _cell_volume 1829.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 4 _cell_measurement_theta_max 28 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.167 _exptl_crystal_density_method ? _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 1.615 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature ? _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 360 _diffrn_standards_decay_% ? _diffrn_reflns_number 2802 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 56.96 _reflns_number_total 2620 _reflns_number_observed 2315 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections jot 213829.txt. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0824P)^2^+1.9985P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0003(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(11) _refine_ls_number_reflns 2617 _refine_ls_number_parameters 422 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_obs 0.0554 _refine_ls_wR_factor_all 0.1571 _refine_ls_wR_factor_obs 0.1413 _refine_ls_goodness_of_fit_all 0.942 _refine_ls_goodness_of_fit_obs 0.941 _refine_ls_restrained_S_all 0.972 _refine_ls_restrained_S_obs 0.941 _refine_ls_shift/esd_max -0.094 _refine_ls_shift/esd_mean 0.019 _refine_ls_special_details ; ; 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.6113(2) 0.0724(3) 0.47686(9) 0.0701(6) Uani 1 d . . S1B S 0.9462(4) 0.4176(3) 0.03714(14) 0.1196(11) Uani 1 d . . O4 O 0.5566(10) -0.1433(5) 0.3092(3) 0.120(3) Uani 1 d . . O10 O 0.6395(5) 0.6216(4) 0.3575(3) 0.0565(12) Uani 1 d . . H10A H 0.5703(5) 0.6512(4) 0.3333(3) 0.085 Uiso 1 calc R . O4B O 0.8198(9) 0.6426(5) 0.1793(4) 0.113(2) Uani 1 d . . O10B O 0.8355(5) -0.1275(4) 0.1352(3) 0.0606(13) Uani 1 d . . H10B H 0.7637(5) -0.1434(4) 0.1079(3) 0.091 Uiso 1 calc R . N3B N 0.9146(6) 0.6443(5) 0.0650(3) 0.067(2) Uani 1 d . . H3BA H 0.9333(6) 0.7211(5) 0.0663(3) 0.080 Uiso 1 calc R . N3 N 0.5713(7) -0.1519(6) 0.4354(3) 0.071(2) Uani 1 d . . H3A H 0.5710(7) -0.2303(6) 0.4370(3) 0.085 Uiso 1 calc R . C2 C 0.5800(9) -0.0820(8) 0.5040(4) 0.076(2) Uani 1 d . . H2A H 0.6577(9) -0.1112(8) 0.5382(4) 0.091 Uiso 1 calc R . H2B H 0.4917(9) -0.0881(8) 0.5286(4) 0.091 Uiso 1 calc R . C4 C 0.5639(9) -0.0945(7) 0.3698(4) 0.069(2) Uani 1 d . . C5 C 0.5600(7) 0.0439(5) 0.3790(3) 0.0515(15) Uani 1 d . . H5A H 0.4617(7) 0.0722(5) 0.3678(3) 0.062 Uiso 1 calc R . C6 C 0.6566(9) 0.1085(7) 0.3266(4) 0.069(2) Uani 1 d . . H6A H 0.7541(9) 0.0814(7) 0.3379(4) 0.083 Uiso 1 calc R . H6B H 0.6282(9) 0.0857(7) 0.2751(4) 0.083 Uiso 1 calc R . C7 C 0.6508(7) 0.2453(6) 0.3338(4) 0.049(2) Uani 1 d . . C12 C 0.5425(7) 0.3119(7) 0.2966(4) 0.054(2) Uani 1 d . . H12A H 0.4738(7) 0.2703(7) 0.2661(4) 0.065 Uiso 1 calc R . C11 C 0.5308(6) 0.4392(6) 0.3023(3) 0.0440(14) Uani 1 d . . C10 C 0.6419(6) 0.4972(6) 0.3458(4) 0.0440(15) Uani 1 d . . C9 C 0.7545(6) 0.4346(6) 0.3842(3) 0.0438(14) Uani 1 d . . C8 C 0.7560(7) 0.3079(7) 0.3761(3) 0.053(2) Uani 1 d . . H8A H 0.8308(7) 0.2639(7) 0.4002(3) 0.064 Uiso 1 calc R . C17 C 0.8735(7) 0.4994(7) 0.4327(4) 0.058(2) Uani 1 d . . C18 C 0.9898(9) 0.4092(10) 0.4631(6) 0.112(4) Uani 1 d . . H18A H 1.0318(55) 0.3706(49) 0.4218(6) 0.168 Uiso 1 calc R . H18B H 0.9479(16) 0.3484(41) 0.4933(34) 0.168 Uiso 1 calc R . H18C H 1.0622(40) 0.4526(15) 0.4932(34) 0.168 Uiso 1 calc R . C19 C 0.8157(9) 0.5600(10) 0.5000(4) 0.092(3) Uani 1 d . . H19A H 0.8920(16) 0.6006(51) 0.5289(20) 0.138 Uiso 1 calc R . H19B H 0.7742(60) 0.4995(12) 0.5306(19) 0.138 Uiso 1 calc R . H19C H 0.7442(51) 0.6186(42) 0.4833(4) 0.138 Uiso 1 calc R . C20 C 0.9473(10) 0.5929(12) 0.3846(5) 0.103(3) Uani 1 d . . H20A H 0.9813(53) 0.5530(15) 0.3414(17) 0.137(44) Uiso 1 calc R . H20B H 1.0264(39) 0.6288(40) 0.4139(11) 0.093(25) Uiso 1 calc R . H20C H 0.8805(20) 0.6555(29) 0.3683(27) 0.172(59) Uiso 1 calc R . C13 C 0.4077(7) 0.5077(7) 0.2598(4) 0.057(2) Uani 1 d . . C16 C 0.3014(10) 0.4214(10) 0.2166(6) 0.101(3) Uani 1 d . . H16A H 0.2667(43) 0.3626(31) 0.2507(8) 0.091(27) Uiso 1 calc R . H16B H 0.3485(18) 0.3799(36) 0.1780(20) 0.111(38) Uiso 1 calc R . H16C H 0.2227(29) 0.4678(11) 0.1941(25) 0.119(32) Uiso 1 calc R . C15 C 0.3230(9) 0.5788(11) 0.3154(4) 0.089(3) Uani 1 d . . H15A H 0.2856(45) 0.5232(11) 0.3506(18) 0.132(37) Uiso 1 calc R . H15B H 0.2456(34) 0.6211(39) 0.2885(5) 0.079(22) Uiso 1 calc R . H15C H 0.3846(17) 0.6368(32) 0.3420(21) 0.100(32) Uiso 1 calc R . C14 C 0.4608(8) 0.5955(8) 0.2011(4) 0.069(2) Uani 1 d . . H14A H 0.3805(8) 0.6295(35) 0.1718(19) 0.130(35) Uiso 1 calc R . H14B H 0.5202(42) 0.5520(12) 0.1686(17) 0.077(23) Uiso 1 calc R . H14C H 0.5149(45) 0.6599(25) 0.2260(4) 0.097(27) Uiso 1 calc R . C2B C 0.9489(11) 0.5741(9) 0.0036(5) 0.099(3) Uani 1 d . . H2BA H 1.0427(11) 0.5954(9) -0.0118(5) 0.118 Uiso 1 calc R . H2BB H 0.8792(11) 0.5857(9) -0.0388(5) 0.118 Uiso 1 calc R . C4B C 0.8525(8) 0.5915(6) 0.1220(4) 0.061(2) Uani 1 d . . C5B C 0.8329(7) 0.4561(5) 0.1085(4) 0.0514(15) Uani 1 d . . H5BA H 0.7339(7) 0.4420(5) 0.0890(4) 0.062 Uiso 1 calc R . C6B C 0.8606(8) 0.3825(6) 0.1793(3) 0.054(2) Uani 1 d . . H6BA H 0.7924(8) 0.4067(6) 0.2148(3) 0.065 Uiso 1 calc R . H6BB H 0.9552(8) 0.4023(6) 0.2016(3) 0.065 Uiso 1 calc R . C7B C 0.8510(7) 0.2462(6) 0.1685(3) 0.048(2) Uani 1 d . . C8B C 0.9569(6) 0.1712(6) 0.2006(3) 0.047(2) Uani 1 d . . H8BA H 1.0351(6) 0.2069(6) 0.2272(3) 0.056 Uiso 1 calc R . C9B C 0.9518(6) 0.0456(6) 0.1947(3) 0.0424(15) Uani 1 d . . C10B C 0.8399(6) -0.0042(5) 0.1498(3) 0.0386(14) Uani 1 d . . C11B C 0.7267(6) 0.0687(6) 0.1165(3) 0.0426(13) Uani 1 d . . C12B C 0.7383(6) 0.1924(5) 0.1272(3) 0.0422(14) Uani 1 d . . H12B H 0.6664(6) 0.2422(5) 0.1055(3) 0.051 Uiso 1 calc R . C13B C 0.5984(6) 0.0111(6) 0.0696(3) 0.051(2) Uani 1 d . . C14B C 0.5219(8) -0.0845(10) 0.1158(4) 0.086(3) Uani 1 d . . H14D H 0.5887(8) -0.1466(10) 0.1330(4) 0.129 Uiso 1 calc R . H14E H 0.4453(8) -0.1209(10) 0.0848(4) 0.129 Uiso 1 calc R . H14F H 0.4842(8) -0.0456(10) 0.1583(4) 0.129 Uiso 1 calc R . C15B C 0.4901(9) 0.1096(9) 0.0428(5) 0.108(3) Uani 1 d . . H15D H 0.4611(59) 0.1543(44) 0.0855(6) 0.162 Uiso 1 calc R . H15E H 0.4082(34) 0.0718(10) 0.0171(36) 0.162 Uiso 1 calc R . H15F H 0.5333(26) 0.1644(39) 0.0092(32) 0.162 Uiso 1 calc R . C16B C 0.6478(8) -0.0507(8) -0.0007(4) 0.078(2) Uani 1 d . . H16D H 0.7118(49) -0.1163(33) 0.0138(4) 0.117 Uiso 1 calc R . H16E H 0.6961(53) 0.0077(14) -0.0299(16) 0.117 Uiso 1 calc R . H16F H 0.5664(11) -0.0824(46) -0.0303(17) 0.117 Uiso 1 calc R . C17B C 1.0706(6) -0.0340(7) 0.2353(3) 0.055(2) Uani 1 d . . C19B C 1.1434(8) -0.1170(9) 0.1804(5) 0.085(3) Uani 1 d . . H19D H 1.0803(28) -0.1827(32) 0.1649(27) 0.128 Uiso 1 calc R . H19E H 1.2297(36) -0.1497(46) 0.2048(12) 0.128 Uiso 1 calc R . H19F H 1.1658(59) -0.0706(15) 0.1371(17) 0.128 Uiso 1 calc R . C20B C 1.0050(8) -0.1147(8) 0.2950(4) 0.082(2) Uani 1 d . . H20D H 0.9321(45) -0.1656(38) 0.2709(6) 0.123 Uiso 1 calc R . H20E H 0.9642(55) -0.0638(8) 0.3315(18) 0.123 Uiso 1 calc R . H20F H 1.0782(15) -0.1649(40) 0.3195(24) 0.123 Uiso 1 calc R . C18B C 1.1866(9) 0.0429(9) 0.2758(5) 0.108(3) Uani 1 d . . H18D H 1.1448(14) 0.0960(50) 0.3109(31) 0.162 Uiso 1 calc R . H18E H 1.2331(55) 0.0909(52) 0.2397(7) 0.162 Uiso 1 calc R . H18F H 1.2552(45) -0.0094(9) 0.3022(36) 0.162 Uiso 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 0.1096(14) 0.0452(10) 0.0557(9) -0.0080(9) 0.0080(9) -0.0034(10) S1B 0.236(3) 0.0395(11) 0.096(2) -0.0006(11) 0.098(2) 0.016(2) O4 0.262(9) 0.036(3) 0.057(3) -0.005(3) -0.031(4) -0.007(4) O10 0.073(3) 0.031(3) 0.064(3) -0.005(2) -0.007(2) 0.007(2) O4B 0.212(7) 0.038(3) 0.098(4) -0.010(3) 0.062(5) 0.008(4) O10B 0.079(3) 0.027(2) 0.074(3) -0.005(2) -0.007(2) -0.003(2) N3B 0.106(4) 0.026(3) 0.071(4) 0.004(3) 0.023(3) -0.009(3) N3 0.110(5) 0.037(4) 0.064(4) 0.005(3) -0.009(3) 0.005(3) C2 0.110(6) 0.051(5) 0.069(4) 0.001(4) 0.024(4) 0.008(4) C4 0.101(5) 0.036(4) 0.067(4) -0.004(4) -0.020(4) -0.001(4) C5 0.062(4) 0.031(3) 0.059(4) -0.003(3) -0.011(3) -0.002(3) C6 0.113(6) 0.035(4) 0.061(4) -0.002(3) 0.019(4) -0.001(4) C7 0.072(4) 0.026(3) 0.051(4) 0.000(3) 0.013(3) 0.000(3) C12 0.068(4) 0.043(4) 0.051(4) -0.010(3) 0.006(3) -0.010(3) C11 0.052(3) 0.037(4) 0.043(3) -0.003(3) 0.005(3) 0.001(3) C10 0.053(4) 0.033(4) 0.046(3) 0.003(3) 0.007(3) -0.002(3) C9 0.055(3) 0.028(3) 0.049(3) -0.001(3) 0.011(3) -0.001(3) C8 0.056(4) 0.052(4) 0.053(4) 0.006(3) 0.011(3) 0.011(3) C17 0.056(4) 0.052(4) 0.066(4) 0.006(3) -0.008(3) -0.001(3) C18 0.079(5) 0.094(7) 0.157(9) -0.006(7) -0.040(6) 0.012(5) C19 0.098(6) 0.109(8) 0.066(4) -0.020(5) -0.012(4) -0.001(6) C20 0.085(6) 0.116(9) 0.105(7) 0.017(7) -0.006(5) -0.055(7) C13 0.062(4) 0.048(4) 0.060(4) 0.006(3) -0.006(3) -0.005(3) C16 0.093(6) 0.081(6) 0.123(7) 0.020(7) -0.046(6) -0.022(6) C15 0.072(4) 0.114(7) 0.079(5) 0.025(6) 0.001(4) 0.034(6) C14 0.096(5) 0.052(4) 0.057(4) 0.007(4) -0.005(4) -0.002(4) C2B 0.163(8) 0.056(5) 0.085(5) -0.002(5) 0.059(5) 0.000(6) C4B 0.092(5) 0.029(3) 0.066(4) -0.004(3) 0.025(4) 0.007(3) C5B 0.062(4) 0.026(3) 0.065(4) 0.001(3) -0.004(3) 0.001(3) C6B 0.080(4) 0.036(4) 0.048(3) -0.002(3) 0.017(3) -0.003(3) C7B 0.068(4) 0.033(4) 0.043(3) -0.006(3) 0.009(3) -0.006(3) C8B 0.055(4) 0.035(4) 0.050(4) 0.002(3) 0.001(3) -0.010(3) C9B 0.045(3) 0.035(4) 0.047(3) 0.006(3) 0.001(3) 0.001(3) C10B 0.055(4) 0.021(3) 0.040(3) -0.003(2) 0.003(3) -0.001(2) C11B 0.049(3) 0.037(3) 0.041(3) 0.002(3) 0.001(2) 0.003(3) C12B 0.056(3) 0.026(3) 0.044(3) 0.005(3) -0.002(3) 0.005(3) C13B 0.053(3) 0.041(4) 0.056(3) -0.005(3) -0.015(3) 0.002(3) C14B 0.070(4) 0.103(7) 0.083(5) 0.002(5) -0.002(4) -0.040(5) C15B 0.089(5) 0.082(6) 0.143(8) -0.009(6) -0.061(6) 0.012(5) C16B 0.098(5) 0.074(6) 0.060(4) -0.012(4) -0.010(4) -0.012(5) C17B 0.051(3) 0.049(4) 0.063(4) 0.007(3) -0.015(3) 0.004(3) C19B 0.067(4) 0.092(6) 0.097(5) -0.005(5) 0.001(4) 0.030(5) C20B 0.090(5) 0.083(6) 0.071(4) 0.031(5) -0.002(4) 0.022(5) C18B 0.095(6) 0.079(7) 0.140(7) -0.003(6) -0.062(6) -0.002(5) _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 C2 1.790(9) . ? S1 C5 1.801(6) . ? S1B C5B 1.770(6) . ? S1B C2B 1.817(11) . ? O4 C4 1.202(9) . ? O10 C10 1.380(8) . ? O4B C4B 1.223(8) . ? O10B C10B 1.376(7) . ? N3B C4B 1.340(8) . ? N3B C2B 1.396(9) . ? N3 C4 1.325(9) . ? N3 C2 1.440(9) . ? C4 C5 1.527(9) . ? C5 C6 1.524(9) . ? C6 C7 1.507(9) . ? C7 C12 1.381(10) . ? C7 C8 1.380(9) . ? C12 C11 1.403(9) . ? C11 C10 1.405(8) . ? C11 C13 1.531(9) . ? C10 C9 1.396(8) . ? C9 C8 1.397(9) . ? C9 C17 1.535(8) . ? C17 C19 1.507(10) . ? C17 C20 1.535(11) . ? C17 C18 1.542(11) . ? C13 C14 1.532(9) . ? C13 C15 1.531(10) . ? C13 C16 1.540(10) . ? C4B C5B 1.513(9) . ? C5B C6B 1.504(9) . ? C6B C7B 1.509(9) . ? C7B C12B 1.376(9) . ? C7B C8B 1.381(9) . ? C8B C9B 1.381(9) . ? C9B C10B 1.385(8) . ? C9B C17B 1.552(8) . ? C10B C11B 1.424(8) . ? C11B C12B 1.372(9) . ? C11B C13B 1.549(8) . ? C13B C15B 1.535(10) . ? C13B C16B 1.527(9) . ? C13B C14B 1.543(10) . ? C17B C18B 1.516(10) . ? C17B C19B 1.535(10) . ? C17B C20B 1.546(9) . ? 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 S1 C5 93.4(3) . . ? C5B S1B C2B 92.1(3) . . ? C4B N3B C2B 119.7(6) . . ? C4 N3 C2 119.5(7) . . ? N3 C2 S1 105.9(5) . . ? O4 C4 N3 125.2(7) . . ? O4 C4 C5 122.6(7) . . ? N3 C4 C5 112.1(6) . . ? C6 C5 C4 112.0(6) . . ? C6 C5 S1 112.6(4) . . ? C4 C5 S1 105.7(5) . . ? C7 C6 C5 112.5(6) . . ? C12 C7 C8 118.2(6) . . ? C12 C7 C6 121.0(7) . . ? C8 C7 C6 120.8(7) . . ? C7 C12 C11 123.3(6) . . ? C12 C11 C10 115.6(6) . . ? C12 C11 C13 120.8(6) . . ? C10 C11 C13 123.6(6) . . ? O10 C10 C9 115.6(5) . . ? O10 C10 C11 120.7(5) . . ? C9 C10 C11 123.5(6) . . ? C8 C9 C10 116.9(6) . . ? C8 C9 C17 120.4(6) . . ? C10 C9 C17 122.8(5) . . ? C7 C8 C9 122.5(6) . . ? C19 C17 C20 110.8(8) . . ? C19 C17 C18 106.9(7) . . ? C20 C17 C18 106.7(7) . . ? C19 C17 C9 111.2(5) . . ? C20 C17 C9 109.6(5) . . ? C18 C17 C9 111.6(6) . . ? C14 C13 C11 112.0(5) . . ? C14 C13 C15 109.5(7) . . ? C11 C13 C15 109.9(5) . . ? C14 C13 C16 106.0(6) . . ? C11 C13 C16 112.5(6) . . ? C15 C13 C16 106.7(7) . . ? N3B C2B S1B 104.6(5) . . ? O4B C4B N3B 125.9(7) . . ? O4B C4B C5B 123.1(6) . . ? N3B C4B C5B 111.0(6) . . ? C4B C5B C6B 112.5(6) . . ? C4B C5B S1B 106.0(5) . . ? C6B C5B S1B 113.6(5) . . ? C5B C6B C7B 114.8(5) . . ? C12B C7B C8B 117.9(6) . . ? C12B C7B C6B 122.0(6) . . ? C8B C7B C6B 120.1(6) . . ? C9B C8B C7B 122.8(6) . . ? C8B C9B C10B 117.2(5) . . ? C8B C9B C17B 120.4(6) . . ? C10B C9B C17B 122.4(5) . . ? O10B C10B C9B 120.5(5) . . ? O10B C10B C11B 117.5(5) . . ? C9B C10B C11B 122.0(5) . . ? C12B C11B C10B 116.6(5) . . ? C12B C11B C13B 121.9(5) . . ? C10B C11B C13B 121.5(6) . . ? C7B C12B C11B 123.2(5) . . ? C15B C13B C16B 107.0(6) . . ? C15B C13B C14B 108.6(6) . . ? C16B C13B C14B 108.6(6) . . ? C15B C13B C11B 110.6(6) . . ? C16B C13B C11B 110.7(5) . . ? C14B C13B C11B 111.3(5) . . ? C18B C17B C19B 107.1(6) . . ? C18B C17B C20B 107.5(6) . . ? C19B C17B C20B 108.6(6) . . ? C18B C17B C9B 112.0(6) . . ? C19B C17B C9B 112.0(5) . . ? C20B C17B C9B 109.5(5) . . ? _refine_diff_density_max 0.424 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.045 _publ_section_references ; Sheldrick, G.M. (1990). SHELXS-86. Acta Cryst. A46, 467-473. Sheldrick, G.M. (1993). SHELXL-93. Program for crystal structure refinement. Institute fur anorg chemie, G\"ottingen, Germany. Siemens Industrial Automation, Incorporated. (1994). SAINT V4; SHELXTL V5; SMART V4. Madison, Wisconsin, USA. ; _publ_section_figure_captions ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; Systematic conditions suggested the un??ambiguous space group. Structure was solved by direct methods (Sheldrick, 1990). Disorder?? Symmetry?? Restraints?? H atom treatment?? The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F^2^ (Sheldrick, 1993). The highest peaks in the final difference Fourier map were in the vicinity of atom ??; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed ?? dependence on amplitude ??and??or?? resolution. ; data_213829 _audit_creation_method SHELXL _audit_update_record ; ? ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H27 N O2 S' _chemical_formula_weight 321.47 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 11.313(3) _cell_length_b 17.082(4) _cell_length_c 19.324(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.11(2) _cell_angle_gamma 90.00 _cell_volume 3664.5(18) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 4 _cell_measurement_theta_max 28 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_method ? _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 1.613 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details '\w scan angle = 0.3\%' _diffrn_ambient_temperature ? _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device 'Siemens Platform' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 360 _diffrn_standards_decay_% ? _diffrn_reflns_number 5221 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 56.99 _reflns_number_total 4928 _reflns_number_observed 3944 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1994)' _computing_cell_refinement 'SAINT (Siemens, 1994)' _computing_data_reduction 'SAINT (Siemens, 1994)' _computing_structure_solution 'SHELXTL (Siemens, 1994)' _computing_structure_refinement 'SHELXTL (Siemens, 1994)' _computing_molecular_graphics 'SHELXTL (Siemens, 1994)' _computing_publication_material 'CIFTAB (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 14 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1164P)^2^+1.9481P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00017(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4914 _refine_ls_number_parameters 399 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_obs 0.0636 _refine_ls_wR_factor_all 0.2203 _refine_ls_wR_factor_obs 0.1911 _refine_ls_goodness_of_fit_all 1.144 _refine_ls_goodness_of_fit_obs 1.174 _refine_ls_restrained_S_all 1.204 _refine_ls_restrained_S_obs 1.174 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_ls_special_details ; ??Methyl H atom positions, R-CH~3~, were optimized by rotation about R-C bonds with idealized C-H, R--H and H--H distances. Remaining H atoms were included as fixed idealized contributors. H atom U's were assigned as 1.2 times Ueq of adjacent non-H atoms. ; 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.91138(10) 0.71667(6) 0.06396(5) 0.0645(4) Uani 1 d . . C2 C 0.8235(4) 0.6434(2) 0.0978(2) 0.0694(11) Uani 1 d . . H2A H 0.7491(4) 0.6336(2) 0.0646(2) 0.083 Uiso 1 calc R . H2B H 0.8682(4) 0.5948(2) 0.1061(2) 0.083 Uiso 1 calc R . N3 N 0.7985(3) 0.6739(2) 0.16285(15) 0.0539(8) Uani 1 d . . H3A H 0.7452(3) 0.6526(2) 0.18300(15) 0.065 Uiso 1 calc R . C4 C 0.8605(3) 0.7361(2) 0.1908(2) 0.0460(8) Uani 1 d . . C5 C 0.9531(3) 0.7640(2) 0.1490(2) 0.0470(8) Uani 1 d . . H5A H 0.9449(3) 0.8207(2) 0.1424(2) 0.056 Uiso 1 calc R . C6 C 1.0810(3) 0.7458(2) 0.1889(2) 0.0500(8) Uani 1 d . . H6A H 1.1377(3) 0.7574(2) 0.1585(2) 0.060 Uiso 1 calc R . H6B H 1.0997(3) 0.7799(2) 0.2297(2) 0.060 Uiso 1 calc R . C7 C 1.0976(3) 0.6618(2) 0.2131(2) 0.0419(7) Uani 1 d . . C8 C 1.1305(3) 0.6044(2) 0.1705(2) 0.0462(8) Uani 1 d . . H8A H 1.1481(3) 0.6188(2) 0.1272(2) 0.055 Uiso 1 calc R . C9 C 1.1387(3) 0.5250(2) 0.1895(2) 0.0409(7) Uani 1 d . . C10 C 1.1108(3) 0.5057(2) 0.2551(2) 0.0409(7) Uani 1 d . . C11 C 1.0834(3) 0.5631(2) 0.3020(2) 0.0408(7) Uani 1 d . . C12 C 1.0769(3) 0.6403(2) 0.2788(2) 0.0437(8) Uani 1 d . . H12A H 1.0579(3) 0.6791(2) 0.3086(2) 0.052 Uiso 1 calc R . C13 C 1.0605(3) 0.5426(2) 0.3758(2) 0.0479(8) Uani 1 d . . C14 C 1.1692(3) 0.4985(2) 0.4194(2) 0.0627(10) Uani 1 d . . H14A H 1.2403(3) 0.5300(2) 0.4230(2) 0.094 Uiso 1 calc R . H14B H 1.1805(3) 0.4499(2) 0.3965(2) 0.094 Uiso 1 calc R . H14C H 1.1541(3) 0.4881(2) 0.4657(2) 0.094 Uiso 1 calc R . C15 C 1.0422(4) 0.6165(2) 0.4184(2) 0.0729(12) Uani 1 d . . H15A H 1.1124(4) 0.6491(2) 0.4233(2) 0.109 Uiso 1 calc R . H15B H 1.0296(4) 0.6015(2) 0.4643(2) 0.109 Uiso 1 calc R . H15C H 0.9733(4) 0.6449(2) 0.3943(2) 0.109 Uiso 1 calc R . C16 C 0.9461(3) 0.4927(2) 0.3697(2) 0.0612(10) Uani 1 d . . H16A H 0.9327(3) 0.4803(2) 0.4160(2) 0.092 Uiso 1 calc R . H16B H 0.9556(3) 0.4452(2) 0.3448(2) 0.092 Uiso 1 calc R . H16C H 0.8784(3) 0.5214(2) 0.3445(2) 0.092 Uiso 1 calc R . C17 C 1.1796(3) 0.4641(2) 0.1400(2) 0.0480(8) Uani 1 d . . C18 C 1.0790(3) 0.4049(2) 0.1133(2) 0.0661(11) Uani 1 d . . H18A H 1.0555(3) 0.3793(2) 0.1527(2) 0.099 Uiso 1 calc R . H18B H 1.1078(3) 0.3666(2) 0.0841(2) 0.099 Uiso 1 calc R . H18C H 1.0109(3) 0.4317(2) 0.0862(2) 0.099 Uiso 1 calc R . C19 C 1.2925(3) 0.4213(2) 0.1786(2) 0.0587(10) Uani 1 d . . H19A H 1.2750(3) 0.3959(2) 0.2198(2) 0.088 Uiso 1 calc R . H19B H 1.3564(3) 0.4584(2) 0.1924(2) 0.088 Uiso 1 calc R . H19C H 1.3166(3) 0.3830(2) 0.1478(2) 0.088 Uiso 1 calc R . C20 C 1.2138(4) 0.5032(3) 0.0753(2) 0.0772(13) Uani 1 d . . H20A H 1.1454(4) 0.5308(3) 0.0495(2) 0.116 Uiso 1 calc R . H20B H 1.2388(4) 0.4639(3) 0.0456(2) 0.116 Uiso 1 calc R . H20C H 1.2787(4) 0.5394(3) 0.0903(2) 0.116 Uiso 1 calc R . O10 O 1.1097(2) 0.43009(13) 0.27856(11) 0.0525(6) Uani 1 d . . H10A H 1.1273(2) 0.40033(13) 0.24882(11) 0.079 Uiso 1 calc R . O4 O 0.8499(2) 0.76616(14) 0.24756(13) 0.0573(7) Uani 1 d . . S1B S 0.60151(11) 0.63727(6) 0.43331(5) 0.0703(4) Uani 1 d . . C2B C 0.6839(4) 0.7132(3) 0.3992(2) 0.0717(11) Uani 1 d . . H2BA H 0.6368(4) 0.7610(3) 0.3920(2) 0.086 Uiso 1 calc R . H2BB H 0.7589(4) 0.7240(3) 0.4316(2) 0.086 Uiso 1 calc R . N3B N 0.7070(3) 0.6838(2) 0.33304(15) 0.0540(8) Uani 1 d . . H3BA H 0.7602(3) 0.7054(2) 0.31293(15) 0.065 Uiso 1 calc R . C4B C 0.6442(3) 0.6227(2) 0.3041(2) 0.0459(8) Uani 1 d . . C5B C 0.5535(3) 0.5934(2) 0.3474(2) 0.0487(8) Uani 1 d . . H5BA H 0.5612(3) 0.5364(2) 0.3522(2) 0.058 Uiso 1 calc R . C6B C 0.4249(3) 0.6130(2) 0.3101(2) 0.0535(9) Uani 1 d . . H6BA H 0.4037(3) 0.5800(2) 0.2687(2) 0.064 Uiso 1 calc R . H6BB H 0.3701(3) 0.6007(2) 0.3415(2) 0.064 Uiso 1 calc R . C7B C 0.4074(3) 0.6976(2) 0.2877(2) 0.0438(8) Uani 1 d . . C8B C 0.3719(3) 0.7542(2) 0.3298(2) 0.0470(8) Uani 1 d . . H8BA H 0.3537(3) 0.7390(2) 0.3728(2) 0.056 Uiso 1 calc R . C9B C 0.3616(3) 0.8331(2) 0.3115(2) 0.0429(8) Uani 1 d . . C10B C 0.3910(3) 0.8540(2) 0.2468(2) 0.0414(8) Uani 1 d . . C11B C 0.4216(3) 0.7978(2) 0.1998(2) 0.0422(8) Uani 1 d . . C12B C 0.4288(3) 0.7203(2) 0.2222(2) 0.0452(8) Uani 1 d . . H12B H 0.4487(3) 0.6821(2) 0.1921(2) 0.054 Uiso 1 calc R . C13B C 0.4472(3) 0.8196(2) 0.1270(2) 0.0502(9) Uani 1 d . . C14B C 0.5591(3) 0.8717(2) 0.1340(2) 0.0602(10) Uani 1 d . . H14D H 0.5733(3) 0.8846(2) 0.0880(2) 0.090 Uiso 1 calc R . H14E H 0.6276(3) 0.8444(2) 0.1600(2) 0.090 Uiso 1 calc R . H14F H 0.5465(3) 0.9190(2) 0.1586(2) 0.090 Uiso 1 calc R . C16B C 0.3371(4) 0.8614(3) 0.0819(2) 0.0760(13) Uani 1 d . . H16D H 0.2675(4) 0.8283(3) 0.0778(2) 0.114 Uiso 1 calc R . H16E H 0.3532(4) 0.8720(3) 0.0359(2) 0.114 Uiso 1 calc R . H16F H 0.3225(4) 0.9097(3) 0.1043(2) 0.114 Uiso 1 calc R . C15B C 0.4722(4) 0.7467(3) 0.0854(2) 0.0748(12) Uani 1 d . . H15D H 0.4040(4) 0.7122(3) 0.0797(2) 0.112 Uiso 1 calc R . H15E H 0.5421(4) 0.7201(3) 0.1107(2) 0.112 Uiso 1 calc R . H15F H 0.4859(4) 0.7622(3) 0.0399(2) 0.112 Uiso 1 calc R . C17B C 0.3165(3) 0.8934(2) 0.3600(2) 0.0522(9) Uani 1 d . . C20B C 0.2068(3) 0.9380(2) 0.3205(2) 0.0592(10) Uani 1 d . . H20D H 0.1443(3) 0.9015(2) 0.3016(2) 0.089 Uiso 1 calc R . H20E H 0.2291(3) 0.9675(2) 0.2828(2) 0.089 Uiso 1 calc R . H20F H 0.1779(3) 0.9731(2) 0.3524(2) 0.089 Uiso 1 calc R . C18B C 0.4161(4) 0.9514(3) 0.3902(2) 0.0826(14) Uani 1 d . . H18D H 0.4849(4) 0.9233(3) 0.4150(2) 0.124 Uiso 1 calc R . H18E H 0.3874(4) 0.9865(3) 0.4222(2) 0.124 Uiso 1 calc R . H18F H 0.4386(4) 0.9809(3) 0.3525(2) 0.124 Uiso 1 calc R . C19B C 0.2736(5) 0.8519(3) 0.4213(2) 0.088(2) Uani 1 d . . H19D H 0.3391(5) 0.8227(3) 0.4483(2) 0.132 Uiso 1 calc R . H19E H 0.2087(5) 0.8170(3) 0.4029(2) 0.132 Uiso 1 calc R . H19F H 0.2462(5) 0.8902(3) 0.4511(2) 0.132 Uiso 1 calc R . O10B O 0.3913(2) 0.93010(14) 0.22399(12) 0.0583(7) Uani 1 d . . H10B H 0.3722(2) 0.95928(14) 0.25368(12) 0.087 Uiso 1 calc R . O4B O 0.6526(2) 0.59311(14) 0.24679(13) 0.0572(7) Uani 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 S1 0.0862(7) 0.0692(7) 0.0401(5) 0.0063(4) 0.0169(5) 0.0012(5) C2 0.082(3) 0.069(3) 0.060(2) -0.013(2) 0.022(2) -0.013(2) N3 0.054(2) 0.058(2) 0.054(2) -0.0061(14) 0.0209(14) -0.0074(14) C4 0.051(2) 0.042(2) 0.048(2) 0.005(2) 0.017(2) 0.008(2) C5 0.062(2) 0.035(2) 0.047(2) 0.0063(14) 0.019(2) 0.004(2) C6 0.055(2) 0.042(2) 0.058(2) 0.002(2) 0.024(2) -0.008(2) C7 0.038(2) 0.044(2) 0.045(2) 0.0048(15) 0.0112(14) -0.0007(14) C8 0.043(2) 0.058(2) 0.041(2) 0.010(2) 0.0164(14) 0.001(2) C9 0.038(2) 0.051(2) 0.036(2) 0.0028(14) 0.0116(13) 0.0027(14) C10 0.040(2) 0.047(2) 0.036(2) 0.0025(14) 0.0094(13) 0.0026(14) C11 0.041(2) 0.049(2) 0.034(2) 0.0020(14) 0.0099(13) 0.0014(14) C12 0.042(2) 0.047(2) 0.043(2) -0.0046(15) 0.0105(14) 0.0021(14) C13 0.056(2) 0.057(2) 0.033(2) -0.0023(15) 0.0144(14) 0.004(2) C14 0.068(2) 0.080(3) 0.038(2) 0.008(2) 0.006(2) 0.012(2) C15 0.110(3) 0.073(3) 0.040(2) -0.003(2) 0.027(2) 0.010(2) C16 0.063(2) 0.078(3) 0.049(2) 0.006(2) 0.026(2) 0.000(2) C17 0.053(2) 0.056(2) 0.039(2) -0.001(2) 0.0200(15) 0.006(2) C18 0.063(2) 0.083(3) 0.054(2) -0.022(2) 0.014(2) 0.002(2) C19 0.050(2) 0.065(2) 0.066(2) -0.005(2) 0.024(2) 0.010(2) C20 0.110(3) 0.081(3) 0.054(2) 0.003(2) 0.048(2) 0.012(3) O10 0.075(2) 0.0434(13) 0.0444(13) 0.0052(10) 0.0264(11) 0.0067(11) O4 0.070(2) 0.0510(14) 0.058(2) -0.0068(12) 0.0296(12) -0.0013(12) S1B 0.1011(8) 0.0732(7) 0.0406(6) 0.0062(4) 0.0238(5) 0.0066(6) C2B 0.086(3) 0.078(3) 0.052(2) -0.013(2) 0.015(2) -0.008(2) N3B 0.053(2) 0.061(2) 0.051(2) -0.0064(14) 0.0173(13) -0.0064(15) C4B 0.051(2) 0.043(2) 0.048(2) 0.003(2) 0.020(2) 0.006(2) C5B 0.067(2) 0.038(2) 0.048(2) 0.0073(15) 0.028(2) 0.006(2) C6B 0.059(2) 0.047(2) 0.062(2) 0.000(2) 0.030(2) -0.005(2) C7B 0.039(2) 0.048(2) 0.047(2) 0.004(2) 0.0153(14) 0.0008(15) C8B 0.044(2) 0.057(2) 0.045(2) 0.006(2) 0.0215(15) 0.005(2) C9B 0.040(2) 0.052(2) 0.039(2) 0.0031(15) 0.0129(14) 0.0088(14) C10B 0.039(2) 0.048(2) 0.039(2) 0.0020(14) 0.0107(13) 0.0061(14) C11B 0.040(2) 0.051(2) 0.036(2) 0.0012(14) 0.0086(13) 0.0011(15) C12B 0.044(2) 0.051(2) 0.043(2) -0.0071(15) 0.0118(14) -0.0003(15) C13B 0.056(2) 0.067(2) 0.030(2) -0.001(2) 0.0118(14) -0.001(2) C14B 0.059(2) 0.077(3) 0.050(2) -0.004(2) 0.025(2) -0.004(2) C16B 0.066(3) 0.111(4) 0.048(2) 0.022(2) 0.002(2) 0.001(2) C15B 0.108(3) 0.078(3) 0.044(2) -0.010(2) 0.027(2) -0.006(3) C17B 0.055(2) 0.060(2) 0.046(2) -0.003(2) 0.020(2) 0.012(2) C20B 0.053(2) 0.060(2) 0.072(2) 0.003(2) 0.029(2) 0.013(2) C18B 0.067(3) 0.104(4) 0.074(3) -0.034(3) 0.009(2) 0.014(2) C19B 0.129(4) 0.095(3) 0.055(2) 0.019(2) 0.054(3) 0.049(3) O10B 0.078(2) 0.0469(14) 0.0567(15) 0.0076(11) 0.0311(13) 0.0099(12) O4B 0.070(2) 0.0536(14) 0.0565(15) -0.0108(12) 0.0337(12) -0.0026(12) _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 C2 1.798(4) . ? S1 C5 1.811(3) . ? C2 N3 1.438(5) . ? N3 C4 1.329(4) . ? C4 O4 1.237(4) . ? C4 C5 1.517(5) . ? C5 C6 1.535(5) . ? C6 C7 1.509(4) . ? C7 C8 1.378(5) . ? C7 C12 1.384(4) . ? C8 C9 1.403(5) . ? C9 C10 1.404(4) . ? C9 C17 1.543(4) . ? C10 O10 1.369(4) . ? C10 C11 1.411(4) . ? C11 C12 1.391(5) . ? C11 C13 1.538(4) . ? C13 C16 1.536(5) . ? C13 C15 1.543(5) . ? C13 C14 1.546(5) . ? C17 C20 1.532(5) . ? C17 C19 1.534(5) . ? C17 C18 1.536(5) . ? S1B C2B 1.794(4) . ? S1B C5B 1.807(4) . ? C2B N3B 1.444(5) . ? N3B C4B 1.324(4) . ? C4B O4B 1.238(4) . ? C4B C5B 1.528(5) . ? C5B C6B 1.531(5) . ? C6B C7B 1.511(5) . ? C7B C8B 1.373(5) . ? C7B C12B 1.388(4) . ? C8B C9B 1.393(5) . ? C9B C10B 1.399(4) . ? C9B C17B 1.546(4) . ? C10B O10B 1.372(4) . ? C10B C11B 1.410(4) . ? C11B C12B 1.390(5) . ? C11B C13B 1.537(4) . ? C13B C14B 1.532(5) . ? C13B C15B 1.537(5) . ? C13B C16B 1.549(5) . ? C17B C20B 1.529(5) . ? C17B C18B 1.529(6) . ? C17B C19B 1.537(5) . ? 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 S1 C5 92.6(2) . . ? N3 C2 S1 106.3(3) . . ? C4 N3 C2 117.9(3) . . ? O4 C4 N3 124.0(3) . . ? O4 C4 C5 122.4(3) . . ? N3 C4 C5 113.5(3) . . ? C4 C5 C6 110.5(3) . . ? C4 C5 S1 104.9(2) . . ? C6 C5 S1 114.9(2) . . ? C7 C6 C5 113.3(3) . . ? C8 C7 C12 118.2(3) . . ? C8 C7 C6 121.6(3) . . ? C12 C7 C6 120.2(3) . . ? C7 C8 C9 122.9(3) . . ? C8 C9 C10 116.7(3) . . ? C8 C9 C17 120.1(3) . . ? C10 C9 C17 123.2(3) . . ? O10 C10 C9 122.6(3) . . ? O10 C10 C11 115.2(3) . . ? C9 C10 C11 122.2(3) . . ? C12 C11 C10 117.2(3) . . ? C12 C11 C13 120.5(3) . . ? C10 C11 C13 122.3(3) . . ? C7 C12 C11 122.7(3) . . ? C16 C13 C11 110.2(3) . . ? C16 C13 C15 107.3(3) . . ? C11 C13 C15 111.9(3) . . ? C16 C13 C14 110.0(3) . . ? C11 C13 C14 111.0(3) . . ? C15 C13 C14 106.4(3) . . ? C20 C17 C19 106.7(3) . . ? C20 C17 C18 107.4(3) . . ? C19 C17 C18 110.1(3) . . ? C20 C17 C9 111.4(3) . . ? C19 C17 C9 109.9(3) . . ? C18 C17 C9 111.2(3) . . ? C2B S1B C5B 92.8(2) . . ? N3B C2B S1B 105.6(3) . . ? C4B N3B C2B 118.3(3) . . ? O4B C4B N3B 124.9(3) . . ? O4B C4B C5B 122.1(3) . . ? N3B C4B C5B 112.9(3) . . ? C4B C5B C6B 110.3(3) . . ? C4B C5B S1B 104.6(2) . . ? C6B C5B S1B 115.6(2) . . ? C7B C6B C5B 113.8(3) . . ? C8B C7B C12B 117.9(3) . . ? C8B C7B C6B 122.7(3) . . ? C12B C7B C6B 119.5(3) . . ? C7B C8B C9B 123.3(3) . . ? C8B C9B C10B 116.9(3) . . ? C8B C9B C17B 120.8(3) . . ? C10B C9B C17B 122.3(3) . . ? O10B C10B C9B 123.0(3) . . ? O10B C10B C11B 114.9(3) . . ? C9B C10B C11B 122.1(3) . . ? C12B C11B C10B 117.1(3) . . ? C12B C11B C13B 120.4(3) . . ? C10B C11B C13B 122.5(3) . . ? C7B C12B C11B 122.6(3) . . ? C14B C13B C11B 111.0(3) . . ? C14B C13B C15B 106.6(3) . . ? C11B C13B C15B 111.6(3) . . ? C14B C13B C16B 110.1(3) . . ? C11B C13B C16B 110.7(3) . . ? C15B C13B C16B 106.8(3) . . ? C20B C17B C18B 109.6(3) . . ? C20B C17B C19B 105.6(3) . . ? C18B C17B C19B 108.9(4) . . ? C20B C17B C9B 111.1(3) . . ? C18B C17B C9B 111.0(3) . . ? C19B C17B C9B 110.5(3) . . ? _refine_diff_density_max 0.316 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.052 _publ_section_references ; ??CSDB??Allen, F.H., Kennard, O. and Taylor, R. (1983). Accounts Chem. Res. 16, 146-153. ??PATSEE??Egert, E. and Sheldrick, G.M. (1985). Acta Cryst. A41, 262-268. ??acentric??Flack, H.D. (1983). Acta Cryst. A39, 876-881. Sheldrick, G.M. (1990). SHELXS-86. Acta Cryst. A46, 467-473. Sheldrick, G.M. (1993). SHELXL-93. Program for crystal structure refinement. Institute fur anorg chemie, G\"ottingen, Germany. Siemens Industrial Automation, Incorporated. (1994). SAINT V4; SHELXTL V5; SMART V4. Madison, Wisconsin, USA. ; _publ_section_figure_captions ; Figure 1. SHELXTL (Siemens, 1994) plot showing 35% probability ellipsoids for non-H atoms and circles of arbitrary size for H atoms. ; _publ_section_exptl_prep ; Synthesis was carried out by reaction of ??. Crystals were grown from ??. The data crystal was mounted using ?? to a thin glass fiber with the (??) scattering planes roughly normal to the spindle axis. ; _publ_section_exptl_refinement ; Systematic conditions suggested the un??ambiguous space group. Structure was solved by direct??Paterson methods (Sheldrick, 1990). Disorder?? Symmetry?? Restraints?? H atom treatment?? The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F^2^ (Sheldrick, 1993). The highest peaks in the final difference Fourier map were in the vicinity of atom ??; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed ?? dependence on amplitude ??and??or?? resolution. ; _publ_contact_author ; Gregory A. Stephenson Eli Lilly and Company Lilly Corporate Center DC3811 Indianapolis, Indiana 46285 USA ; _publ_contact_author_phone '1 317 277 3841' _publ_contact_author_fax '1 317 277 8386' _publ_contact_author_email gas@lilly.com _publ_contact_letter ; Please consider this CIF submission for publication as a structural paper in Acta Crystallographica C. The figure and list of structure factors will be sent by normal mail. ; _publ_requested_journal 'Acta Crystallographica C' _publ_requested_coeditor_name ? _publ_section_title ; ? ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_acknowledgements ; ? ; loop_ _publ_author_name _publ_author_address 'Scott R. Wilson' ; University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ; 'Teresa Prussak-Wieckowska' ; University of Illinois School of Chemical Sciences, Box 59-1 505 South Mathews Avenue Urbana, Illinois 61801 USA ;