# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Shengming Ma' _publ_contact_author_address ; 354 Fenglin Lu Shanghai 200032 ; _publ_contact_author_email masm@mail.sioc.ac.cn _publ_section_title ; Studies on Highly Regio- and Stereoselective Hydration of 1,2-Allenylic Sulfoxides ; _publ_author_name 'Shengming Ma.' # Attachment '- R-Z-3d.cif' data_z-R-Z-3d _database_code_depnum_ccdc_archive 'CCDC 772770' #TrackingRef '- R-Z-3d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2.33 H3.33 O0.33 S0.17' _chemical_formula_weight 42.06 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' 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 Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.4734(6) _cell_length_b 9.0484(10) _cell_length_c 14.9986(18) _cell_angle_alpha 83.446(5) _cell_angle_beta 89.906(5) _cell_angle_gamma 89.581(4) _cell_volume 737.94(15) _cell_formula_units_Z 12 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.440 _exptl_crystal_size_mid 0.425 _exptl_crystal_size_min 0.147 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.136 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.209 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.711701 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10241 _diffrn_reflns_av_R_equivalents 0.1050 _diffrn_reflns_av_sigmaI/netI 0.2217 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4695 _reflns_number_gt 2287 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0198P)^2^+0.2209P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.12(8) _chemical_absolute_configuration ad _refine_ls_number_reflns 4695 _refine_ls_number_parameters 307 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1844 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1170 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.000 _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 S 0.9480(3) 0.47865(14) 0.12390(11) 0.0616(5) Uani 1 1 d . . . S2 S 0.4475(3) -0.02151(15) 0.12305(11) 0.0619(5) Uani 1 1 d . . . O1 O 1.5143(7) 0.5164(4) -0.0666(3) 0.0763(13) Uani 1 1 d . . . H1D H 1.5750 0.5050 -0.0163 0.115 Uiso 1 1 calc R . . O2 O 0.6732(8) 0.4728(4) 0.1142(3) 0.0821(13) Uani 1 1 d . . . O3 O 1.0173(7) 0.0126(4) -0.0686(3) 0.0750(13) Uani 1 1 d . . . H3C H 1.0788 0.0038 -0.0184 0.113 Uiso 1 1 calc R . . O4 O 0.1737(8) -0.0190(4) 0.1115(3) 0.0802(13) Uani 1 1 d . . . C1 C 1.0485(18) 0.2053(9) -0.4119(5) 0.158(4) Uani 1 1 d . . . H1A H 1.1086 0.1169 -0.4346 0.238 Uiso 1 1 calc R . . H1B H 1.0771 0.2898 -0.4553 0.238 Uiso 1 1 calc R . . H1C H 0.8763 0.1959 -0.4005 0.238 Uiso 1 1 calc R . . C2 C 1.1744(16) 0.2251(8) -0.3291(5) 0.107(3) Uani 1 1 d . . . H2A H 1.3481 0.2320 -0.3417 0.128 Uiso 1 1 calc R . . H2B H 1.1495 0.1368 -0.2871 0.128 Uiso 1 1 calc R . . C3 C 1.0990(12) 0.3590(6) -0.2837(4) 0.085(2) Uani 1 1 d . . . H3A H 1.1315 0.4481 -0.3242 0.102 Uiso 1 1 calc R . . H3B H 0.9242 0.3549 -0.2731 0.102 Uiso 1 1 calc R . . C4 C 1.2257(11) 0.3720(6) -0.1959(4) 0.070(2) Uani 1 1 d . . . H4A H 1.4005 0.3774 -0.2064 0.084 Uiso 1 1 calc R . . H4B H 1.1945 0.2827 -0.1553 0.084 Uiso 1 1 calc R . . C5 C 1.1459(10) 0.5063(5) -0.1508(4) 0.0619(16) Uani 1 1 d . . . H5A H 1.1929 0.5960 -0.1885 0.074 Uiso 1 1 calc R . . H5B H 0.9692 0.5066 -0.1459 0.074 Uiso 1 1 calc R . . C6 C 1.2537(11) 0.5096(6) -0.0593(4) 0.0577(16) Uani 1 1 d . . . H6A H 1.2086 0.4184 -0.0213 0.069 Uiso 1 1 calc R . . C7 C 1.1628(9) 0.6429(5) -0.0159(4) 0.0579(16) Uani 1 1 d . . . H7A H 1.1948 0.7358 -0.0468 0.069 Uiso 1 1 calc R . . C8 C 1.0453(9) 0.6427(5) 0.0597(4) 0.0563(16) Uani 1 1 d . . . H8A H 1.0111 0.7334 0.0807 0.068 Uiso 1 1 calc R . . C9 C 0.9988(14) 0.5331(7) 0.2323(5) 0.062(3) Uani 1 1 d . . . C10 C 1.1983(13) 0.6098(8) 0.2545(5) 0.085(2) Uani 1 1 d . . . H10A H 1.3162 0.6382 0.2113 0.102 Uiso 1 1 calc R . . C11 C 1.2269(15) 0.6462(9) 0.3420(5) 0.098(2) Uani 1 1 d . . . H11A H 1.3605 0.7022 0.3560 0.117 Uiso 1 1 calc R . . C12 C 1.067(2) 0.6020(10) 0.4049(6) 0.102(4) Uani 1 1 d . . . H12A H 1.0885 0.6271 0.4627 0.122 Uiso 1 1 calc R . . C13 C 0.8638(15) 0.5177(10) 0.3860(5) 0.105(2) Uani 1 1 d . . . H13A H 0.7536 0.4831 0.4307 0.126 Uiso 1 1 calc R . . C14 C 0.8329(13) 0.4871(8) 0.2972(5) 0.092(2) Uani 1 1 d . . . H14A H 0.6964 0.4345 0.2823 0.111 Uiso 1 1 calc R . . C15 C 0.5217(18) -0.2865(9) -0.4157(5) 0.159(4) Uani 1 1 d . . . H15A H 0.5763 -0.3731 -0.4416 0.238 Uiso 1 1 calc R . . H15B H 0.5473 -0.1997 -0.4577 0.238 Uiso 1 1 calc R . . H15C H 0.3509 -0.2954 -0.4016 0.238 Uiso 1 1 calc R . . C16 C 0.6626(16) -0.2727(8) -0.3319(5) 0.108(3) Uani 1 1 d . . . H16A H 0.8351 -0.2666 -0.3467 0.129 Uiso 1 1 calc R . . H16B H 0.6388 -0.3622 -0.2907 0.129 Uiso 1 1 calc R . . C17 C 0.5924(12) -0.1399(6) -0.2851(4) 0.085(2) Uani 1 1 d . . . H17A H 0.4182 -0.1437 -0.2731 0.101 Uiso 1 1 calc R . . H17B H 0.6231 -0.0504 -0.3256 0.101 Uiso 1 1 calc R . . C18 C 0.7254(11) -0.1283(6) -0.1981(4) 0.0700(19) Uani 1 1 d . . . H18A H 0.8996 -0.1237 -0.2099 0.084 Uiso 1 1 calc R . . H18B H 0.6950 -0.2176 -0.1574 0.084 Uiso 1 1 calc R . . C19 C 0.6503(10) 0.0064(5) -0.1522(4) 0.0632(16) Uani 1 1 d . . . H19A H 0.7008 0.0958 -0.1894 0.076 Uiso 1 1 calc R . . H19B H 0.4736 0.0091 -0.1477 0.076 Uiso 1 1 calc R . . C20 C 0.7568(11) 0.0075(6) -0.0605(4) 0.0587(16) Uani 1 1 d . . . H20A H 0.7103 -0.0839 -0.0231 0.070 Uiso 1 1 calc R . . C21 C 0.6712(10) 0.1403(5) -0.0163(4) 0.0594(16) Uani 1 1 d . . . H21A H 0.7063 0.2329 -0.0469 0.071 Uiso 1 1 calc R . . C22 C 0.5546(9) 0.1416(5) 0.0592(4) 0.0581(16) Uani 1 1 d . . . H22A H 0.5262 0.2327 0.0807 0.070 Uiso 1 1 calc R . . C23 C 0.5008(14) 0.0319(7) 0.2316(5) 0.064(3) Uani 1 1 d . . . C24 C 0.7017(13) -0.0224(8) 0.2811(5) 0.093(2) Uani 1 1 d . . . H24A H 0.8138 -0.0848 0.2572 0.112 Uiso 1 1 calc R . . C25 C 0.7340(15) 0.0172(11) 0.3668(5) 0.113(3) Uani 1 1 d . . . H25A H 0.8684 -0.0195 0.4004 0.136 Uiso 1 1 calc R . . C26 C 0.574(2) 0.1084(11) 0.4025(6) 0.115(4) Uani 1 1 d . . . H26A H 0.5988 0.1345 0.4599 0.138 Uiso 1 1 calc R . . C27 C 0.3752(16) 0.1620(9) 0.3542(5) 0.102(2) Uani 1 1 d . . . H27A H 0.2660 0.2249 0.3792 0.122 Uiso 1 1 calc R . . C28 C 0.3325(11) 0.1246(7) 0.2686(5) 0.0800(19) Uani 1 1 d . . . H28A H 0.1951 0.1604 0.2365 0.096 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 0.0695(13) 0.0482(10) 0.0687(10) -0.0137(8) -0.0060(11) 0.0025(8) S2 0.0658(12) 0.0493(10) 0.0722(11) -0.0144(8) -0.0050(11) -0.0019(8) O1 0.046(3) 0.090(3) 0.094(3) -0.016(3) -0.006(3) 0.005(2) O2 0.071(4) 0.086(3) 0.092(3) -0.020(2) -0.010(3) -0.017(2) O3 0.057(3) 0.082(3) 0.088(3) -0.017(2) -0.014(3) 0.011(2) O4 0.068(3) 0.085(3) 0.091(3) -0.022(2) -0.010(3) -0.019(2) C1 0.213(12) 0.169(8) 0.105(7) -0.065(6) -0.036(8) 0.023(7) C2 0.130(8) 0.101(6) 0.095(6) -0.038(5) -0.012(6) 0.019(5) C3 0.100(6) 0.081(5) 0.075(5) -0.017(4) -0.016(4) 0.013(4) C4 0.074(5) 0.063(4) 0.073(4) -0.011(3) -0.004(4) 0.012(3) C5 0.060(5) 0.057(4) 0.069(4) -0.009(3) -0.002(4) 0.008(3) C6 0.060(5) 0.049(4) 0.064(4) -0.005(3) -0.004(4) 0.010(3) C7 0.064(5) 0.043(3) 0.066(4) -0.004(3) -0.009(4) -0.002(3) C8 0.062(4) 0.045(3) 0.065(4) -0.016(3) -0.012(3) 0.003(3) C9 0.050(6) 0.066(5) 0.070(6) -0.005(5) -0.008(6) 0.006(5) C10 0.067(5) 0.101(5) 0.091(6) -0.027(4) -0.012(4) -0.001(4) C11 0.093(6) 0.117(6) 0.083(6) -0.011(5) -0.013(5) -0.023(5) C12 0.114(10) 0.119(8) 0.074(8) -0.020(7) -0.014(8) -0.002(8) C13 0.089(6) 0.147(7) 0.078(6) 0.000(5) 0.017(5) -0.015(5) C14 0.077(6) 0.118(6) 0.084(6) -0.020(4) -0.010(5) -0.013(4) C15 0.208(12) 0.175(9) 0.105(8) -0.069(7) -0.015(8) -0.009(7) C16 0.108(7) 0.121(7) 0.102(7) -0.047(6) 0.001(6) 0.007(5) C17 0.095(6) 0.081(5) 0.081(5) -0.021(4) -0.008(4) 0.011(4) C18 0.079(5) 0.063(4) 0.069(4) -0.016(3) -0.009(4) 0.010(3) C19 0.064(5) 0.058(4) 0.067(4) -0.004(3) -0.001(4) 0.010(3) C20 0.065(5) 0.050(4) 0.062(4) -0.009(3) -0.005(4) 0.006(3) C21 0.068(5) 0.042(3) 0.068(4) -0.008(3) -0.008(4) 0.000(3) C22 0.063(4) 0.045(4) 0.069(4) -0.019(3) -0.014(4) 0.003(3) C23 0.058(7) 0.069(5) 0.066(6) -0.005(5) -0.003(6) -0.001(5) C24 0.070(6) 0.117(6) 0.091(6) -0.010(4) -0.012(5) 0.001(4) C25 0.096(7) 0.174(8) 0.068(6) -0.002(5) -0.024(5) -0.013(6) C26 0.129(12) 0.156(11) 0.066(8) -0.028(8) -0.004(9) -0.044(9) C27 0.101(7) 0.122(6) 0.087(6) -0.036(5) 0.006(5) -0.008(5) C28 0.064(5) 0.091(5) 0.088(5) -0.025(4) -0.009(4) 0.001(4) _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 O2 1.513(4) . ? S1 C8 1.760(5) . ? S1 C9 1.775(7) . ? S2 O4 1.509(4) . ? S2 C22 1.769(5) . ? S2 C23 1.775(7) . ? O1 C6 1.432(6) . ? O1 H1D 0.8200 . ? O3 C20 1.431(6) . ? O3 H3C 0.8200 . ? C1 C2 1.451(9) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.510(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.506(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.518(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.499(7) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.516(6) . ? C6 H6A 0.9800 . ? C7 C8 1.302(6) . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? C9 C10 1.360(10) . ? C9 C14 1.362(10) . ? C10 C11 1.399(9) . ? C10 H10A 0.9300 . ? C11 C12 1.318(11) . ? C11 H11A 0.9300 . ? C12 C13 1.399(11) . ? C12 H12A 0.9300 . ? C13 C14 1.401(9) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C16 1.493(9) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.506(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.511(7) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.520(6) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.496(7) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.509(6) . ? C20 H20A 0.9800 . ? C21 C22 1.300(6) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C23 C24 1.383(10) . ? C23 C28 1.398(8) . ? C24 C25 1.386(10) . ? C24 H24A 0.9300 . ? C25 C26 1.351(11) . ? C25 H25A 0.9300 . ? C26 C27 1.362(12) . ? C26 H26A 0.9300 . ? C27 C28 1.385(9) . ? C27 H27A 0.9300 . ? C28 H28A 0.9300 . ? 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 O2 S1 C8 106.9(2) . . ? O2 S1 C9 105.3(3) . . ? C8 S1 C9 98.5(3) . . ? O4 S2 C22 105.8(2) . . ? O4 S2 C23 105.7(3) . . ? C22 S2 C23 98.2(3) . . ? C6 O1 H1D 109.5 . . ? C20 O3 H3C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C1 C2 C3 116.3(6) . . ? C1 C2 H2A 108.2 . . ? C3 C2 H2A 108.2 . . ? C1 C2 H2B 108.2 . . ? C3 C2 H2B 108.2 . . ? H2A C2 H2B 107.4 . . ? C4 C3 C2 114.7(5) . . ? C4 C3 H3A 108.6 . . ? C2 C3 H3A 108.6 . . ? C4 C3 H3B 108.6 . . ? C2 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? C3 C4 C5 113.9(5) . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4B 108.8 . . ? C5 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 113.4(4) . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5B 108.9 . . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? O1 C6 C5 109.2(5) . . ? O1 C6 C7 108.9(5) . . ? C5 C6 C7 111.5(4) . . ? O1 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C8 C7 C6 127.6(5) . . ? C8 C7 H7A 116.2 . . ? C6 C7 H7A 116.2 . . ? C7 C8 S1 123.0(4) . . ? C7 C8 H8A 118.5 . . ? S1 C8 H8A 118.5 . . ? C10 C9 C14 119.1(7) . . ? C10 C9 S1 123.8(6) . . ? C14 C9 S1 117.0(6) . . ? C9 C10 C11 120.2(7) . . ? C9 C10 H10A 119.9 . . ? C11 C10 H10A 119.9 . . ? C12 C11 C10 120.6(8) . . ? C12 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? C11 C12 C13 121.1(9) . . ? C11 C12 H12A 119.5 . . ? C13 C12 H12A 119.5 . . ? C12 C13 C14 117.5(7) . . ? C12 C13 H13A 121.2 . . ? C14 C13 H13A 121.2 . . ? C9 C14 C13 121.3(7) . . ? C9 C14 H14A 119.4 . . ? C13 C14 H14A 119.4 . . ? C16 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C15 C16 C17 114.2(7) . . ? C15 C16 H16A 108.7 . . ? C17 C16 H16A 108.7 . . ? C15 C16 H16B 108.7 . . ? C17 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? C16 C17 C18 114.8(5) . . ? C16 C17 H17A 108.6 . . ? C18 C17 H17A 108.6 . . ? C16 C17 H17B 108.6 . . ? C18 C17 H17B 108.6 . . ? H17A C17 H17B 107.5 . . ? C17 C18 C19 113.7(5) . . ? C17 C18 H18A 108.8 . . ? C19 C18 H18A 108.8 . . ? C17 C18 H18B 108.8 . . ? C19 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C20 C19 C18 113.7(4) . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19B 108.8 . . ? C18 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? O3 C20 C19 108.4(5) . . ? O3 C20 C21 108.7(5) . . ? C19 C20 C21 112.0(5) . . ? O3 C20 H20A 109.3 . . ? C19 C20 H20A 109.3 . . ? C21 C20 H20A 109.3 . . ? C22 C21 C20 128.2(5) . . ? C22 C21 H21A 115.9 . . ? C20 C21 H21A 115.9 . . ? C21 C22 S2 123.1(4) . . ? C21 C22 H22A 118.5 . . ? S2 C22 H22A 118.5 . . ? C24 C23 C28 119.9(7) . . ? C24 C23 S2 120.6(5) . . ? C28 C23 S2 119.5(6) . . ? C23 C24 C25 119.2(7) . . ? C23 C24 H24A 120.4 . . ? C25 C24 H24A 120.4 . . ? C26 C25 C24 121.2(9) . . ? C26 C25 H25A 119.4 . . ? C24 C25 H25A 119.4 . . ? C25 C26 C27 119.9(9) . . ? C25 C26 H26A 120.0 . . ? C27 C26 H26A 120.0 . . ? C26 C27 C28 121.3(8) . . ? C26 C27 H27A 119.3 . . ? C28 C27 H27A 119.3 . . ? C27 C28 C23 118.5(7) . . ? C27 C28 H28A 120.8 . . ? C23 C28 H28A 120.8 . . ? 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 C1 C2 C3 C4 177.4(7) . . . . ? C2 C3 C4 C5 -179.4(6) . . . . ? C3 C4 C5 C6 174.0(5) . . . . ? C4 C5 C6 O1 61.4(6) . . . . ? C4 C5 C6 C7 -178.3(5) . . . . ? O1 C6 C7 C8 -118.4(6) . . . . ? C5 C6 C7 C8 121.1(6) . . . . ? C6 C7 C8 S1 -4.8(9) . . . . ? O2 S1 C8 C7 -107.7(5) . . . . ? C9 S1 C8 C7 143.3(5) . . . . ? O2 S1 C9 C10 -151.3(6) . . . . ? C8 S1 C9 C10 -41.2(7) . . . . ? O2 S1 C9 C14 32.3(6) . . . . ? C8 S1 C9 C14 142.5(6) . . . . ? C14 C9 C10 C11 -2.6(11) . . . . ? S1 C9 C10 C11 -178.9(5) . . . . ? C9 C10 C11 C12 2.6(11) . . . . ? C10 C11 C12 C13 0.0(14) . . . . ? C11 C12 C13 C14 -2.4(13) . . . . ? C10 C9 C14 C13 0.1(11) . . . . ? S1 C9 C14 C13 176.6(6) . . . . ? C12 C13 C14 C9 2.4(11) . . . . ? C15 C16 C17 C18 177.4(7) . . . . ? C16 C17 C18 C19 -179.8(6) . . . . ? C17 C18 C19 C20 172.4(5) . . . . ? C18 C19 C20 O3 62.0(6) . . . . ? C18 C19 C20 C21 -178.1(5) . . . . ? O3 C20 C21 C22 -118.9(7) . . . . ? C19 C20 C21 C22 121.4(7) . . . . ? C20 C21 C22 S2 -5.5(9) . . . . ? O4 S2 C22 C21 -107.3(5) . . . . ? C23 S2 C22 C21 143.8(5) . . . . ? O4 S2 C23 C24 149.2(6) . . . . ? C22 S2 C23 C24 -101.8(6) . . . . ? O4 S2 C23 C28 -28.1(6) . . . . ? C22 S2 C23 C28 80.9(6) . . . . ? C28 C23 C24 C25 -0.5(11) . . . . ? S2 C23 C24 C25 -177.8(6) . . . . ? C23 C24 C25 C26 -0.3(12) . . . . ? C24 C25 C26 C27 0.5(14) . . . . ? C25 C26 C27 C28 0.2(14) . . . . ? C26 C27 C28 C23 -1.1(11) . . . . ? C24 C23 C28 C27 1.2(10) . . . . ? S2 C23 C28 C27 178.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.253 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.047 # Attachment '- S-Z-3d.cif' data_z-S-Z-3d _database_code_depnum_ccdc_archive 'CCDC 772771' #TrackingRef '- S-Z-3d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 O2 S' _chemical_formula_weight 252.36 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' 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.9143(10) _cell_length_b 6.0830(7) _cell_length_c 13.2938(15) _cell_angle_alpha 90.00 _cell_angle_beta 93.159(3) _cell_angle_gamma 90.00 _cell_volume 719.77(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9087 _exptl_absorpt_correction_T_max 0.9797 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7777 _diffrn_reflns_av_R_equivalents 0.0467 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2365 _reflns_number_gt 2178 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0645P)^2^+0.1754P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.12(10) _chemical_absolute_configuration ad _refine_ls_number_reflns 2365 _refine_ls_number_parameters 154 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.000 _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 S 0.84575(6) 0.14863(10) 0.43857(4) 0.02541(18) Uani 1 1 d . . . O1 O 0.9143(2) 0.2301(3) 0.53779(13) 0.0348(5) Uani 1 1 d . . . O2 O 1.0942(2) -0.2610(3) 0.25774(14) 0.0350(5) Uani 1 1 d . . . H2A H 1.1160 -0.2910 0.3185 0.052 Uiso 1 1 calc R . . C1 C 0.6980(3) 0.3391(5) 0.40398(18) 0.0269(6) Uani 1 1 d . . . C2 C 0.6928(3) 0.5405(5) 0.4512(2) 0.0311(6) Uani 1 1 d . . . H2B H 0.7690 0.5814 0.5004 0.037 Uiso 1 1 calc R . . C3 C 0.5755(3) 0.6822(5) 0.4262(2) 0.0366(7) Uani 1 1 d . . . H3A H 0.5705 0.8213 0.4584 0.044 Uiso 1 1 calc R . . C4 C 0.4650(3) 0.6206(6) 0.3538(2) 0.0427(8) Uani 1 1 d . . . H4A H 0.3840 0.7176 0.3368 0.051 Uiso 1 1 calc R . . C5 C 0.4725(3) 0.4208(6) 0.3069(2) 0.0459(8) Uani 1 1 d . . . H5A H 0.3971 0.3816 0.2568 0.055 Uiso 1 1 calc R . . C6 C 0.5887(3) 0.2743(5) 0.3315(2) 0.0376(7) Uani 1 1 d . . . H6A H 0.5932 0.1347 0.2998 0.045 Uiso 1 1 calc R . . C7 C 0.9709(3) 0.2377(5) 0.34941(19) 0.0300(6) Uani 1 1 d . . . H7A H 1.0092 0.3832 0.3548 0.036 Uiso 1 1 calc R . . C8 C 1.0148(3) 0.1118(5) 0.27479(19) 0.0304(7) Uani 1 1 d . . . H8A H 1.0848 0.1751 0.2318 0.037 Uiso 1 1 calc R . . C9 C 0.9662(3) -0.1189(5) 0.25100(18) 0.0281(6) Uani 1 1 d . . . H9A H 0.8923 -0.1676 0.3004 0.034 Uiso 1 1 calc R . . C10 C 0.8943(3) -0.1361(5) 0.14411(19) 0.0326(6) Uani 1 1 d . . . H10A H 0.8130 -0.0256 0.1357 0.039 Uiso 1 1 calc R . . H10B H 0.9708 -0.1007 0.0954 0.039 Uiso 1 1 calc R . . C11 C 0.8295(3) -0.3629(6) 0.11967(19) 0.0373(6) Uani 1 1 d . . . H11A H 0.7557 -0.4016 0.1698 0.045 Uiso 1 1 calc R . . H11B H 0.9112 -0.4732 0.1246 0.045 Uiso 1 1 calc R . . C12 C 0.7529(3) -0.3708(6) 0.01423(18) 0.0363(6) Uani 1 1 d . . . H12A H 0.6747 -0.2553 0.0083 0.044 Uiso 1 1 calc R . . H12B H 0.8280 -0.3389 -0.0359 0.044 Uiso 1 1 calc R . . C13 C 0.6811(4) -0.5929(6) -0.0094(2) 0.0492(8) Uani 1 1 d . . . H13A H 0.7602 -0.7073 -0.0068 0.059 Uiso 1 1 calc R . . H13B H 0.6100 -0.6283 0.0429 0.059 Uiso 1 1 calc R . . C14 C 0.5976(4) -0.5993(8) -0.1122(2) 0.0576(10) Uani 1 1 d . . . H14A H 0.5525 -0.7448 -0.1231 0.086 Uiso 1 1 calc R . . H14B H 0.6680 -0.5698 -0.1646 0.086 Uiso 1 1 calc R . . H14C H 0.5184 -0.4873 -0.1151 0.086 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 0.0295(3) 0.0205(3) 0.0252(3) -0.0005(3) -0.0069(2) 0.0002(3) O1 0.0413(10) 0.0371(11) 0.0244(9) -0.0043(8) -0.0134(7) 0.0039(9) O2 0.0352(10) 0.0365(11) 0.0324(10) -0.0007(8) -0.0050(8) 0.0068(9) C1 0.0252(13) 0.0277(14) 0.0270(13) 0.0055(11) -0.0063(10) -0.0014(11) C2 0.0268(13) 0.0268(15) 0.0389(14) 0.0001(12) -0.0050(11) -0.0025(12) C3 0.0335(13) 0.0249(19) 0.0517(16) 0.0057(13) 0.0057(12) 0.0043(12) C4 0.0318(13) 0.043(2) 0.0533(17) 0.0202(17) -0.0026(12) 0.0091(16) C5 0.0357(16) 0.058(2) 0.0422(17) 0.0086(16) -0.0140(13) 0.0003(15) C6 0.0415(16) 0.0376(18) 0.0322(15) -0.0027(13) -0.0115(12) -0.0008(13) C7 0.0271(13) 0.0251(13) 0.0366(15) 0.0011(11) -0.0084(10) -0.0033(11) C8 0.0264(12) 0.0311(18) 0.0332(13) 0.0053(12) -0.0038(10) -0.0036(12) C9 0.0298(13) 0.0303(15) 0.0237(13) 0.0000(11) -0.0025(10) -0.0001(12) C10 0.0360(15) 0.0351(17) 0.0259(13) 0.0024(11) -0.0048(11) 0.0001(12) C11 0.0447(14) 0.0357(15) 0.0302(12) -0.0023(16) -0.0098(10) -0.0047(18) C12 0.0345(13) 0.0440(18) 0.0296(12) -0.0049(16) -0.0047(10) 0.0022(17) C13 0.0525(18) 0.053(2) 0.0409(17) -0.0048(16) -0.0076(14) -0.0131(16) C14 0.0500(19) 0.082(3) 0.0397(17) -0.0229(18) -0.0057(14) -0.0188(19) _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 O1 1.5064(17) . ? S1 C7 1.758(3) . ? S1 C1 1.795(3) . ? O2 C9 1.430(3) . ? O2 H2A 0.8400 . ? C1 C2 1.379(4) . ? C1 C6 1.389(3) . ? C2 C3 1.381(4) . ? C2 H2B 0.9500 . ? C3 C4 1.390(4) . ? C3 H3A 0.9500 . ? C4 C5 1.370(5) . ? C4 H4A 0.9500 . ? C5 C6 1.392(4) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.329(4) . ? C7 H7A 0.9500 . ? C8 C9 1.498(4) . ? C8 H8A 0.9500 . ? C9 C10 1.530(3) . ? C9 H9A 1.0000 . ? C10 C11 1.524(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.526(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.521(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.520(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 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 O1 S1 C7 104.32(12) . . ? O1 S1 C1 105.58(12) . . ? C7 S1 C1 96.46(12) . . ? C9 O2 H2A 109.5 . . ? C2 C1 C6 121.9(2) . . ? C2 C1 S1 119.98(18) . . ? C6 C1 S1 118.1(2) . . ? C1 C2 C3 119.3(2) . . ? C1 C2 H2B 120.3 . . ? C3 C2 H2B 120.3 . . ? C2 C3 C4 119.7(3) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4A 119.9 . . ? C3 C4 H4A 119.9 . . ? C4 C5 C6 121.0(3) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C1 C6 C5 117.8(3) . . ? C1 C6 H6A 121.1 . . ? C5 C6 H6A 121.1 . . ? C8 C7 S1 123.3(2) . . ? C8 C7 H7A 118.3 . . ? S1 C7 H7A 118.3 . . ? C7 C8 C9 127.1(3) . . ? C7 C8 H8A 116.4 . . ? C9 C8 H8A 116.4 . . ? O2 C9 C8 109.4(2) . . ? O2 C9 C10 108.0(2) . . ? C8 C9 C10 111.2(2) . . ? O2 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C11 C10 C9 113.2(2) . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C10 C11 C12 111.7(3) . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 107.9 . . ? C13 C12 C11 112.3(3) . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? C11 C12 H12B 109.1 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 112.8(3) . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 O1 S1 C1 C2 15.8(2) . . . . ? C7 S1 C1 C2 -91.0(2) . . . . ? O1 S1 C1 C6 -162.3(2) . . . . ? C7 S1 C1 C6 90.9(2) . . . . ? C6 C1 C2 C3 0.2(4) . . . . ? S1 C1 C2 C3 -177.8(2) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? C2 C3 C4 C5 -0.4(4) . . . . ? C3 C4 C5 C6 1.0(5) . . . . ? C2 C1 C6 C5 0.4(4) . . . . ? S1 C1 C6 C5 178.4(2) . . . . ? C4 C5 C6 C1 -1.0(5) . . . . ? O1 S1 C7 C8 136.3(2) . . . . ? C1 S1 C7 C8 -115.8(2) . . . . ? S1 C7 C8 C9 1.5(4) . . . . ? C7 C8 C9 O2 -119.3(3) . . . . ? C7 C8 C9 C10 121.5(3) . . . . ? O2 C9 C10 C11 65.4(3) . . . . ? C8 C9 C10 C11 -174.6(2) . . . . ? C9 C10 C11 C12 177.5(2) . . . . ? C10 C11 C12 C13 -177.2(3) . . . . ? C11 C12 C13 C14 177.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.302 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.052