# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Healy, P.' 'Loughlin, Wendy' 'Rowen, Catherine C.' _publ_contact_author_name 'Dr Wendy Loughlin' _publ_contact_author_address ; School of Science, Griffith University, Nathan Queensland, Australia 4111. ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' 617 3875 7442' _publ_contact_author_fax ' 617 3875 7656 ' _publ_contact_author_email 'W.LOUGHLIN@SCT.GU.EDU.AU' _publ_section_title ; Investigations into the reaction of the lithium enolate of cyclohexanone and phenyl vinyl sulfoxide: A simple synthesis of a bicyclo[4.2.0]octan-1-ol ; #============================================================================== data__473wl19_64phenylA _database_code_CSD 170562 #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows version 1.06 (MSC, 1997-2001)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan for Windows version 1.06 (MSC, 1997-2001)' _computing_publication_material 'teXsan for Windows version 1.06 (MSC, 1997-2001)' #------------------------------------------------------------------------------ _cell_length_a 11.296(3) _cell_length_b 22.296(3) _cell_length_c 10.547(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2656(1) _cell_formula_units_Z 8 _cell_measurement_temperature 295.2 _cell_measurement_reflns_used 13 _cell_measurement_theta_min 12.9 _cell_measurement_theta_max 14.8 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_Int_Tables_number 61 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2+x,1/2-y, -z' ' -x,1/2+y,1/2-z' '1/2-x, -y,1/2+z' ' -x, -y, -z' '1/2-x,1/2+y, +z' ' +x,1/2-y,1/2+z' '1/2+x, +y,1/2-z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 250.35 _chemical_formula_analytical ? _chemical_formula_sum 'C14 H18 O2 S ' _chemical_formula_moiety 'C14 H18 O2 S ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1072.00 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type none _exptl_special_details ; The scan width was (1.05+0.30tan\q)\% with an \w scan speed of 16\% per minute (up to 5 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 295.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC7R' _diffrn_measurement_method \w _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -0.22 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 0 2 0 0 2 0 4 2 _diffrn_reflns_number 3573 _reflns_number_total 2699 _reflns_number_gt 1015 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.03433 _diffrn_reflns_av_sigmaI/netI 0.121 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.00272 _diffrn_orient_matrix_UB_12 0.01997 _diffrn_orient_matrix_UB_13 0.08481 _diffrn_orient_matrix_UB_21 0.02434 _diffrn_orient_matrix_UB_22 0.03878 _diffrn_orient_matrix_UB_23 -0.03989 _diffrn_orient_matrix_UB_31 -0.08488 _diffrn_orient_matrix_UB_32 0.01049 _diffrn_orient_matrix_UB_33 -0.01413 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 112 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 144 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 16 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; S 0 8 0.110 0.124 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom S1 -0.1726(1) -0.09362(5) -0.6407(1) 0.0517(4) 1.000 . Uani d ? O1 -0.1256(3) 0.0374(1) -0.4307(3) 0.058(1) 1.000 . Uani d ? O2 -0.0659(2) -0.1113(1) -0.5616(3) 0.069(1) 1.000 . Uani d ? C1 -0.1952(4) 0.0268(2) -0.5370(4) 0.041(1) 1.000 . Uani d ? C2 -0.1386(4) 0.0486(2) -0.6603(4) 0.053(2) 1.000 . Uani d ? C3 -0.1606(5) 0.1153(2) -0.6824(5) 0.073(2) 1.000 . Uani d ? C4 -0.2936(5) 0.1276(2) -0.6944(5) 0.087(2) 1.000 . Uani d ? C5 -0.3588(4) 0.1098(2) -0.5736(5) 0.070(2) 1.000 . Uani d ? C6 -0.3266(4) 0.0475(2) -0.5277(4) 0.048(1) 1.000 . Uani d ? C7 -0.3653(4) -0.0108(2) -0.5964(4) 0.055(2) 1.000 . Uani d ? C8 -0.2486(4) -0.0374(2) -0.5492(4) 0.046(1) 1.000 . Uani d ? C9 -0.2817(4) -0.1517(2) -0.6194(4) 0.043(1) 1.000 . Uani d ? C10 -0.3745(5) -0.1566(2) -0.7022(4) 0.062(2) 1.000 . Uani d ? C11 -0.4591(5) -0.1999(2) -0.6805(5) 0.077(2) 1.000 . Uani d ? C12 -0.4492(5) -0.2384(2) -0.5833(6) 0.084(2) 1.000 . Uani d ? C13 -0.3546(5) -0.2342(2) -0.5031(6) 0.082(2) 1.000 . Uani d ? C14 -0.2684(4) -0.1904(2) -0.5191(5) 0.062(2) 1.000 . Uani d ? H2a -0.1712 0.0266 -0.7290 0.063 1.000 . Uiso c ? H2b -0.0557 0.0417 -0.6562 0.063 1.000 . Uiso c ? H3a -0.1220 0.1274 -0.7583 0.088 1.000 . Uiso c ? H3b -0.1297 0.1375 -0.6130 0.088 1.000 . Uiso c ? H4a -0.3244 0.1051 -0.7634 0.105 1.000 . Uiso c ? H4b -0.3056 0.1691 -0.7097 0.105 1.000 . Uiso c ? H5a -0.4415 0.1111 -0.5895 0.084 1.000 . Uiso c ? H5b -0.3396 0.1378 -0.5089 0.084 1.000 . Uiso c ? H6 -0.3502 0.0443 -0.4415 0.057 1.000 . Uiso c ? H7b -0.4345 -0.0292 -0.5633 0.066 1.000 . Uiso c ? H7a -0.3720 -0.0075 -0.6860 0.066 1.000 . Uiso c ? H8 -0.2610 -0.0528 -0.4663 0.055 1.000 . Uiso c ? H10 -0.3804 -0.1307 -0.7734 0.074 1.000 . Uiso c ? H11 -0.5257 -0.2026 -0.7353 0.092 1.000 . Uiso c ? H12 -0.5076 -0.2684 -0.5703 0.101 1.000 . Uiso c ? H13 -0.3475 -0.2619 -0.4350 0.098 1.000 . Uiso c ? H14 -0.2030 -0.1873 -0.4629 0.075 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0421(7) 0.0550(7) 0.0580(7) -0.0014(7) 0.0086(8) -0.0041(7) O1 0.054(2) 0.076(2) 0.043(2) -0.005(2) -0.015(2) -0.009(2) O2 0.035(2) 0.077(2) 0.093(3) 0.007(2) -0.008(2) -0.006(2) C1 0.032(3) 0.047(3) 0.045(3) -0.000(2) 0.005(2) 0.002(2) C2 0.046(3) 0.056(3) 0.057(3) -0.002(2) 0.012(3) -0.003(3) C3 0.090(5) 0.056(3) 0.074(4) 0.002(3) 0.030(4) 0.009(3) C4 0.116(6) 0.071(4) 0.075(4) 0.036(4) 0.017(4) 0.017(3) C5 0.058(4) 0.079(4) 0.074(4) 0.016(3) -0.003(3) -0.009(3) C6 0.038(3) 0.056(3) 0.049(3) 0.007(3) -0.005(3) -0.003(3) C7 0.034(3) 0.072(4) 0.059(3) -0.004(3) 0.010(3) -0.012(3) C8 0.041(3) 0.059(3) 0.037(3) -0.000(3) 0.009(3) -0.004(3) C9 0.039(3) 0.046(3) 0.043(3) -0.000(2) 0.008(2) -0.007(3) C10 0.058(3) 0.064(4) 0.064(4) -0.002(3) -0.016(3) -0.011(3) C11 0.054(4) 0.062(4) 0.114(6) -0.006(3) -0.021(4) -0.024(4) C12 0.062(4) 0.061(4) 0.130(6) -0.008(4) 0.018(4) -0.004(4) C13 0.105(5) 0.054(4) 0.086(5) 0.003(4) 0.019(4) 0.022(3) C14 0.065(4) 0.057(3) 0.065(4) 0.003(3) -0.002(3) 0.003(3) #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00000|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.00000039(1) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1015 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1792 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_all 0.0460 _refine_ls_wR_factor_ref 0.0380 _refine_ls_goodness_of_fit_all 1.398 _refine_ls_goodness_of_fit_ref 1.840 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0004 _refine_diff_density_min -0.25 _refine_diff_density_max 0.23 #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.518(4) . . ? S1 C8 1.799(6) . . ? S1 C9 1.801(5) . . ? O1 C1 1.390(6) . . ? C1 C2 1.528(7) . . ? C1 C6 1.557(7) . . ? C1 C8 1.558(7) . . ? C2 C3 1.528(7) . . ? C2 H2a 0.95 . . no C2 H2b 0.95 . . no C3 C4 1.533(9) . . ? C3 H3a 0.95 . . no C3 H3b 0.95 . . no C4 C5 1.524(9) . . ? C4 H4a 0.95 . . no C4 H4b 0.95 . . no C5 C6 1.516(8) . . ? C5 H5a 0.95 . . no C5 H5b 0.95 . . no C6 C7 1.551(7) . . ? C6 H6 0.95 . . no C7 C8 1.529(8) . . ? C7 H7b 0.95 . . no C7 H7a 0.95 . . no C8 H8 0.95 . . no C9 C10 1.369(7) . . ? C9 C14 1.374(7) . . ? C10 C11 1.378(8) . . ? C10 H10 0.95 . . no C11 C12 1.341(9) . . ? C11 H11 0.95 . . no C12 C13 1.366(9) . . ? C12 H12 0.95 . . no C13 C14 1.390(9) . . ? C13 H13 0.95 . . no C14 H14 0.95 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 C8 105.4(3) . . . ? O2 S1 C9 106.8(3) . . . ? C8 S1 C9 96.2(3) . . . ? O1 C1 C2 113.3(5) . . . ? O1 C1 C6 116.0(5) . . . ? O1 C1 C8 116.3(5) . . . ? C2 C1 C6 111.0(5) . . . ? C2 C1 C8 112.5(5) . . . ? C6 C1 C8 84.8(4) . . . ? C1 C2 C3 111.8(5) . . . ? C1 C2 H2a 108.9 . . . no C1 C2 H2b 108.9 . . . no C3 C2 H2a 108.9 . . . no C3 C2 H2b 108.9 . . . no H2a C2 H2b 109.5 . . . no C2 C3 C4 110.2(6) . . . ? C2 C3 H3a 109.3 . . . no C2 C3 H3b 109.3 . . . no C4 C3 H3a 109.3 . . . no C4 C3 H3b 109.3 . . . no H3a C3 H3b 109.5 . . . no C3 C4 C5 111.0(6) . . . ? C3 C4 H4a 109.1 . . . no C3 C4 H4b 109.1 . . . no C5 C4 H4a 109.1 . . . no C5 C4 H4b 109.1 . . . no H4a C4 H4b 109.5 . . . no C4 C5 C6 112.9(6) . . . ? C4 C5 H5a 108.6 . . . no C4 C5 H5b 108.6 . . . no C6 C5 H5a 108.6 . . . no C6 C5 H5b 108.6 . . . no H5a C5 H5b 109.5 . . . no C1 C6 C5 118.7(5) . . . ? C1 C6 C7 89.5(4) . . . ? C1 C6 H6 107.8 . . . no C5 C6 C7 123.5(5) . . . ? C5 C6 H6 107.8 . . . no C7 C6 H6 107.8 . . . no C6 C7 C8 86.0(4) . . . ? C6 C7 H7b 115.0 . . . no C6 C7 H7a 115.0 . . . no C8 C7 H7b 115.0 . . . no C8 C7 H7a 115.0 . . . no H7b C7 H7a 109.5 . . . no S1 C8 C1 120.0(4) . . . ? S1 C8 C7 120.4(4) . . . ? S1 C8 H8 108.2 . . . no C1 C8 C7 90.3(4) . . . ? C1 C8 H8 108.2 . . . no C7 C8 H8 108.2 . . . no S1 C9 C10 120.2(5) . . . ? S1 C9 C14 118.2(5) . . . ? C10 C9 C14 121.6(6) . . . ? C9 C10 C11 118.8(6) . . . ? C9 C10 H10 120.6 . . . no C11 C10 H10 120.6 . . . no C10 C11 C12 121.1(7) . . . ? C10 C11 H11 119.4 . . . no C12 C11 H11 119.4 . . . no C11 C12 C13 119.7(8) . . . ? C11 C12 H12 120.2 . . . no C13 C12 H12 120.2 . . . no C12 C13 C14 121.4(7) . . . ? C12 C13 H13 119.3 . . . no C14 C13 H13 119.3 . . . no C9 C14 C13 117.3(6) . . . ? C9 C14 H14 121.3 . . . no C13 C14 H14 121.3 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 H10 2.6610 . 4_455 no O1 H7a 2.6659 . 4_455 no O1 O2 2.720(5) . 5_554 no O1 H2b 2.8543 . 5_554 no O1 C7 3.576(7) . 4_455 no O1 C10 3.588(7) . 4_455 no O2 H10 2.7574 . 8_553 no O2 H3b 2.9353 . 5_554 no O2 H11 2.9901 . 8_553 no O2 C10 3.450(7) . 8_553 no O2 C11 3.572(9) . 8_553 no O2 C2 3.573(7) . 5_554 no C6 H7b 2.8935 . 5_454 no C7 H7b 2.9583 . 5_454 no C12 H3b 2.9226 . 6_445 no H2a H8 2.6814 . 4_454 no H3a H5a 2.6200 . 8_553 no H3b H12 2.6471 . 6_455 no H4a H8 2.6206 . 4_454 no H6 H7b 2.4558 . 5_454 no H7b H7b 2.3816 . 5_454 no H12 H14 2.4424 . 2_444 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag S1 C8 C1 O1 . . . . -94.5(6) no S1 C8 C1 C2 . . . . 38.6(7) no S1 C8 C1 C6 . . . . 149.1(4) no S1 C8 C7 C6 . . . . -148.8(4) no S1 C9 C10 C11 . . . . -177.3(5) no S1 C9 C14 C13 . . . . 178.9(5) no O1 C1 C2 C3 . . . . -83.4(7) no O1 C1 C6 C5 . . . . 91.9(7) no O1 C1 C6 C7 . . . . -139.5(5) no O1 C1 C8 C7 . . . . 139.6(5) no O2 S1 C8 C1 . . . . 72.8(5) no O2 S1 C8 C7 . . . . -177.0(5) no O2 S1 C9 C10 . . . . -163.3(5) no O2 S1 C9 C14 . . . . 16.5(6) no C1 C2 C3 C4 . . . . -61.8(8) no C1 C6 C5 C4 . . . . 39.6(8) no C1 C6 C7 C8 . . . . 23.2(4) no C1 C8 S1 C9 . . . . -177.9(5) no C1 C8 C7 C6 . . . . -23.2(4) no C2 C1 C6 C5 . . . . -39.2(7) no C2 C1 C6 C7 . . . . 89.4(5) no C2 C1 C8 C7 . . . . -87.4(5) no C2 C3 C4 C5 . . . . 60.9(8) no C3 C2 C1 C6 . . . . 49.1(7) no C3 C2 C1 C8 . . . . 142.2(6) no C3 C4 C5 C6 . . . . -49.0(8) no C4 C5 C6 C7 . . . . -70.9(8) no C5 C6 C1 C8 . . . . -151.4(5) no C5 C6 C7 C8 . . . . 148.0(6) no C6 C1 C8 C7 . . . . 23.1(4) no C7 C6 C1 C8 . . . . -22.8(4) no C7 C8 S1 C9 . . . . -67.7(5) no C8 S1 C9 C10 . . . . 88.6(5) no C8 S1 C9 C14 . . . . -91.7(5) no C9 C10 C11 C12 . . . . -3(1) no C9 C14 C13 C12 . . . . -1(1) no C10 C9 C14 C13 . . . . -1(1) no C10 C11 C12 C13 . . . . 1(1) no C11 C10 C9 C14 . . . . 3(1) no C11 C12 C13 C14 . . . . 1(1) no #------------------------------------------------------------------------------ #============================================================================== data__467wl17_64phenylB _database_code_CSD 170563 #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows version 1.06 (MSC, 1997-2001)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan for Windows version 1.06 (MSC, 1997-2001)' _computing_publication_material 'teXsan for Windows version 1.06 (MSC, 1997-2001)' #------------------------------------------------------------------------------ _cell_length_a 12.719(6) _cell_length_b 19.14(1) _cell_length_c 11.106(7) _cell_angle_alpha 90 _cell_angle_beta 102.55(5) _cell_angle_gamma 90 _cell_volume 2639(3) _cell_formula_units_Z 8 _cell_measurement_temperature 295.2 _cell_measurement_reflns_used 20 _cell_measurement_theta_min 12.6 _cell_measurement_theta_max 16.3 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y, -z' ' -x, -y, -z' '1/2+x,1/2-y, +z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 250.35 _chemical_formula_analytical ? _chemical_formula_sum 'C14 H18 O2 S ' _chemical_formula_moiety '?' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1072.00 _exptl_absorpt_coefficient_mu 0.233 _exptl_absorpt_correction_type none _exptl_special_details ; The scan width was (1.63+0.30tan\q)\% with an \w scan speed of 16\% per minute (up to 5 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 295.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 8.11 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 -4 -1 3 -4 -2 2 0 -5 _diffrn_reflns_number 5373 _reflns_number_total 4807 _reflns_number_gt 1474 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.13951 _diffrn_reflns_av_sigmaI/netI 0.210 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.03209 _diffrn_orient_matrix_UB_12 -0.02172 _diffrn_orient_matrix_UB_13 -0.06562 _diffrn_orient_matrix_UB_21 0.03442 _diffrn_orient_matrix_UB_22 -0.03680 _diffrn_orient_matrix_UB_23 0.05959 _diffrn_orient_matrix_UB_31 -0.06539 _diffrn_orient_matrix_UB_32 -0.03006 _diffrn_orient_matrix_UB_33 -0.02555 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 112 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 144 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 16 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; S 0 8 0.110 0.124 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom S1 0.7778(2) 0.4477(1) 0.5886(2) 0.0485(7) 1.000 . Uani d ? S2 0.6344(2) 0.6891(1) 0.7312(2) 0.0523(8) 1.000 . Uani d ? O1 0.6467(4) 0.4068(3) 0.3447(5) 0.051(2) 1.000 . Uani d ? O2 0.6983(4) 0.4058(3) 0.6414(5) 0.067(2) 1.000 . Uani d ? O3 0.4969(4) 0.6471(3) 0.4926(5) 0.056(2) 1.000 . Uani d ? O4 0.5592(4) 0.6442(3) 0.7855(6) 0.079(2) 1.000 . Uani d ? C1 0.6525(6) 0.4806(4) 0.3584(7) 0.043(3) 1.000 . Uani d ? C2 0.5476(6) 0.5154(4) 0.2981(7) 0.045(3) 1.000 . Uani d ? C3 0.5355(6) 0.5259(5) 0.1598(8) 0.057(3) 1.000 . Uani d ? C4 0.6275(9) 0.5728(5) 0.1391(8) 0.081(4) 1.000 . Uani d ? C5 0.7387(7) 0.5381(5) 0.1861(8) 0.070(4) 1.000 . Uani d ? C6 0.7502(6) 0.5120(4) 0.3156(7) 0.053(3) 1.000 . Uani d ? C7 0.7637(7) 0.5612(4) 0.4293(8) 0.066(3) 1.000 . Uani d ? C8 0.6980(6) 0.5110(4) 0.4888(7) 0.039(3) 1.000 . Uani d ? C9 0.8391(6) 0.5054(4) 0.7085(7) 0.043(3) 1.000 . Uani d ? C10 0.9454(7) 0.5243(5) 0.7179(9) 0.070(4) 1.000 . Uani d ? C11 0.9980(7) 0.5696(6) 0.811(1) 0.083(4) 1.000 . Uani d ? C12 0.9429(8) 0.5901(5) 0.9005(9) 0.077(4) 1.000 . Uani d ? C13 0.8357(9) 0.5716(5) 0.8898(8) 0.070(4) 1.000 . Uani d ? C14 0.7829(6) 0.5283(5) 0.7964(8) 0.058(3) 1.000 . Uani d ? C15 0.5000(6) 0.7208(4) 0.5056(7) 0.043(3) 1.000 . Uani d ? C16 0.3901(6) 0.7539(4) 0.4521(8) 0.052(3) 1.000 . Uani d ? C17 0.3727(8) 0.7666(5) 0.3154(9) 0.071(4) 1.000 . Uani d ? C18 0.4611(8) 0.8142(5) 0.2870(8) 0.080(4) 1.000 . Uani d ? C19 0.5715(7) 0.7805(5) 0.3288(8) 0.061(3) 1.000 . Uani d ? C20 0.5913(6) 0.7570(4) 0.4612(7) 0.050(3) 1.000 . Uani d ? C21 0.6071(6) 0.8061(4) 0.5727(7) 0.050(3) 1.000 . Uani d ? C22 0.5466(6) 0.7514(4) 0.6359(7) 0.041(3) 1.000 . Uani d ? C23 0.6936(6) 0.7479(4) 0.8493(7) 0.045(3) 1.000 . Uani d ? C24 0.7905(7) 0.7818(5) 0.8490(8) 0.060(3) 1.000 . Uani d ? C25 0.8358(7) 0.8290(5) 0.941(1) 0.069(4) 1.000 . Uani d ? C26 0.7854(9) 0.8407(5) 1.0355(9) 0.066(4) 1.000 . Uani d ? C27 0.6900(8) 0.8063(6) 1.0388(9) 0.076(4) 1.000 . Uani d ? C28 0.6432(7) 0.7594(5) 0.9465(9) 0.062(3) 1.000 . Uani d ? H2a 0.5443 0.5597 0.3355 0.054 1.000 . Uiso c ? H2b 0.4898 0.4871 0.3113 0.054 1.000 . Uiso c ? H3a 0.5388 0.4820 0.1210 0.068 1.000 . Uiso c ? H3b 0.4683 0.5475 0.1265 0.068 1.000 . Uiso c ? H4a 0.6179 0.5816 0.0531 0.097 1.000 . Uiso c ? H4b 0.6253 0.6155 0.1816 0.097 1.000 . Uiso c ? H5a 0.7461 0.5000 0.1338 0.084 1.000 . Uiso c ? H5b 0.7935 0.5716 0.1843 0.084 1.000 . Uiso c ? H6 0.8067 0.4786 0.3313 0.064 1.000 . Uiso c ? H7b 0.8361 0.5665 0.4735 0.079 1.000 . Uiso c ? H7a 0.7316 0.6058 0.4116 0.079 1.000 . Uiso c ? H8 0.6453 0.5333 0.5243 0.048 1.000 . Uiso c ? H10 0.9835 0.5065 0.6599 0.085 1.000 . Uiso c ? H11 1.0691 0.5855 0.8139 0.100 1.000 . Uiso c ? H12 0.9787 0.6169 0.9693 0.093 1.000 . Uiso c ? H13 0.7976 0.5893 0.9479 0.084 1.000 . Uiso c ? H14 0.7105 0.5142 0.7921 0.070 1.000 . Uiso c ? H16a 0.3857 0.7973 0.4922 0.063 1.000 . Uiso c ? H16b 0.3353 0.7235 0.4669 0.063 1.000 . Uiso c ? H17a 0.3742 0.7232 0.2745 0.086 1.000 . Uiso c ? H17b 0.3046 0.7882 0.2871 0.086 1.000 . Uiso c ? H18a 0.4476 0.8222 0.2006 0.097 1.000 . Uiso c ? H18b 0.4600 0.8573 0.3288 0.097 1.000 . Uiso c ? H19a 0.5759 0.7412 0.2781 0.073 1.000 . Uiso c ? H19b 0.6251 0.8136 0.3205 0.073 1.000 . Uiso c ? H20 0.6507 0.7257 0.4746 0.060 1.000 . Uiso c ? H21b 0.6801 0.8135 0.6130 0.060 1.000 . Uiso c ? H21a 0.5716 0.8498 0.5566 0.060 1.000 . Uiso c ? H22 0.4937 0.7710 0.6743 0.050 1.000 . Uiso c ? H24 0.8267 0.7723 0.7844 0.072 1.000 . Uiso c ? H25 0.9008 0.8528 0.9385 0.083 1.000 . Uiso c ? H26 0.8154 0.8725 1.0995 0.079 1.000 . Uiso c ? H27 0.6559 0.8150 1.1054 0.091 1.000 . Uiso c ? H28 0.5782 0.7359 0.9501 0.074 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.044(1) 0.042(1) 0.060(2) -0.002(1) 0.012(1) -0.006(1) S2 0.052(2) 0.044(2) 0.060(2) -0.003(1) 0.010(1) 0.000(1) O1 0.056(4) 0.029(3) 0.069(4) -0.006(3) 0.013(3) -0.011(3) O2 0.076(4) 0.055(4) 0.076(4) -0.028(4) 0.028(4) 0.004(4) O3 0.048(4) 0.028(4) 0.092(5) 0.003(3) 0.017(3) -0.019(3) O4 0.068(4) 0.061(5) 0.110(5) -0.026(3) 0.025(4) 0.021(4) C1 0.040(6) 0.040(5) 0.057(6) 0.005(4) 0.025(5) 0.001(5) C2 0.049(6) 0.041(6) 0.046(6) 0.006(4) 0.015(4) -0.011(5) C3 0.047(6) 0.064(7) 0.060(7) 0.011(5) 0.010(5) 0.006(5) C4 0.112(9) 0.065(8) 0.063(7) -0.022(7) 0.015(7) 0.007(6) C5 0.074(7) 0.096(8) 0.047(6) -0.032(6) 0.031(5) -0.007(6) C6 0.052(6) 0.068(7) 0.042(6) -0.020(5) 0.018(5) -0.009(5) C7 0.066(6) 0.047(6) 0.079(7) -0.015(5) 0.006(5) 0.005(6) C8 0.024(5) 0.042(6) 0.054(6) 0.008(4) 0.012(4) 0.004(5) C9 0.046(6) 0.042(6) 0.043(5) -0.005(4) 0.015(5) 0.000(4) C10 0.055(7) 0.067(7) 0.094(8) -0.002(6) 0.027(6) -0.017(6) C11 0.058(7) 0.093(9) 0.102(9) -0.014(6) 0.027(7) -0.027(7) C12 0.065(7) 0.067(8) 0.088(8) -0.019(6) -0.008(7) -0.013(6) C13 0.092(8) 0.073(8) 0.043(6) -0.007(6) 0.007(6) -0.006(6) C14 0.054(6) 0.069(7) 0.052(6) -0.013(5) 0.014(5) -0.007(5) C15 0.030(5) 0.046(6) 0.056(6) -0.005(4) 0.019(4) -0.009(5) C16 0.043(6) 0.057(6) 0.056(6) 0.000(5) 0.008(5) -0.000(5) C17 0.073(7) 0.042(7) 0.094(8) -0.004(5) 0.005(6) 0.001(6) C18 0.094(8) 0.085(9) 0.066(7) -0.002(7) 0.027(6) 0.028(6) C19 0.070(7) 0.060(7) 0.054(6) -0.017(5) 0.019(5) -0.009(5) C20 0.046(5) 0.060(6) 0.044(6) -0.003(5) 0.011(5) -0.007(5) C21 0.045(5) 0.047(6) 0.059(6) -0.005(5) 0.013(4) 0.003(5) C22 0.045(5) 0.035(5) 0.050(6) 0.004(4) 0.022(4) 0.011(5) C23 0.030(5) 0.053(6) 0.051(6) -0.004(4) 0.006(5) 0.009(5) C24 0.050(6) 0.068(7) 0.068(7) 0.003(5) 0.029(5) -0.004(6) C25 0.060(7) 0.072(8) 0.076(8) -0.032(6) 0.017(6) -0.011(6) C26 0.089(8) 0.050(7) 0.051(7) -0.001(6) 0.001(6) -0.002(5) C27 0.068(7) 0.11(1) 0.058(7) 0.001(7) 0.028(6) 0.024(7) C28 0.055(6) 0.070(7) 0.052(6) -0.010(6) -0.010(5) 0.016(6) #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00015|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1474 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.2982 _refine_ls_R_factor_gt 0.0720 _refine_ls_wR_factor_all 0.0970 _refine_ls_wR_factor_ref 0.0730 _refine_ls_goodness_of_fit_all 1.399 _refine_ls_goodness_of_fit_ref 2.030 _refine_ls_shift/su_max 2.3500 _refine_ls_shift/su_mean 0.0087 _refine_diff_density_min -0.32 _refine_diff_density_max 0.40 #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.506(7) . . ? S1 C8 1.80(1) . . ? S1 C9 1.77(1) . . ? S2 O4 1.507(7) . . ? S2 C22 1.81(1) . . ? S2 C23 1.77(1) . . ? O1 C1 1.42(1) . . ? O3 C15 1.42(1) . . ? C1 C2 1.51(1) . . ? C1 C6 1.54(1) . . ? C1 C8 1.55(1) . . ? C2 C3 1.52(2) . . ? C2 H2a 0.95 . . no C2 H2b 0.95 . . no C3 C4 1.53(2) . . ? C3 H3a 0.95 . . no C3 H3b 0.95 . . no C4 C5 1.55(2) . . ? C4 H4a 0.95 . . no C4 H4b 0.95 . . no C5 C6 1.50(1) . . ? C5 H5a 0.95 . . no C5 H5b 0.95 . . no C6 C7 1.56(2) . . ? C6 H6 0.95 . . no C7 C8 1.52(1) . . ? C7 H7b 0.95 . . no C7 H7a 0.95 . . no C8 H8 0.95 . . no C9 C10 1.38(1) . . ? C9 C14 1.40(1) . . ? C10 C11 1.41(2) . . ? C10 H10 0.95 . . no C11 C12 1.39(2) . . ? C11 H11 0.95 . . no C12 C13 1.39(2) . . ? C12 H12 0.95 . . no C13 C14 1.38(2) . . ? C13 H13 0.95 . . no C14 H14 0.95 . . no C15 C16 1.53(1) . . ? C15 C20 1.52(1) . . ? C15 C22 1.55(1) . . ? C16 C17 1.51(2) . . ? C16 H16a 0.95 . . no C16 H16b 0.95 . . no C17 C18 1.53(2) . . ? C17 H17a 0.95 . . no C17 H17b 0.95 . . no C18 C19 1.52(2) . . ? C18 H18a 0.95 . . no C18 H18b 0.95 . . no C19 C20 1.51(1) . . ? C19 H19a 0.95 . . no C19 H19b 0.95 . . no C20 C21 1.53(1) . . ? C20 H20 0.95 . . no C21 C22 1.55(1) . . ? C21 H21b 0.95 . . no C21 H21a 0.95 . . no C22 H22 0.95 . . no C23 C24 1.39(1) . . ? C23 C28 1.39(1) . . ? C24 C25 1.39(2) . . ? C24 H24 0.95 . . no C25 C26 1.36(2) . . ? C25 H25 0.95 . . no C26 C27 1.39(2) . . ? C26 H26 0.95 . . no C27 C28 1.39(2) . . ? C27 H27 0.95 . . no C28 H28 0.95 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 C8 105.1(5) . . . ? O2 S1 C9 105.2(5) . . . ? C8 S1 C9 98.0(5) . . . ? O4 S2 C22 104.2(5) . . . ? O4 S2 C23 105.8(5) . . . ? C22 S2 C23 97.2(5) . . . ? O1 C1 C2 111.7(9) . . . ? O1 C1 C6 112.3(9) . . . ? O1 C1 C8 118.2(9) . . . ? C2 C1 C6 113(1) . . . ? C2 C1 C8 111.2(9) . . . ? C6 C1 C8 88.9(8) . . . ? C1 C2 C3 113.0(9) . . . ? C1 C2 H2a 108.6 . . . no C1 C2 H2b 108.5 . . . no C3 C2 H2a 108.6 . . . no C3 C2 H2b 108.5 . . . no H2a C2 H2b 109.5 . . . no C2 C3 C4 108(1) . . . ? C2 C3 H3a 109.7 . . . no C2 C3 H3b 109.7 . . . no C4 C3 H3a 109.8 . . . no C4 C3 H3b 109.7 . . . no H3a C3 H3b 109.5 . . . no C3 C4 C5 112(1) . . . ? C3 C4 H4a 108.7 . . . no C3 C4 H4b 108.9 . . . no C5 C4 H4a 108.9 . . . no C5 C4 H4b 109.1 . . . no H4a C4 H4b 109.6 . . . no C4 C5 C6 111(1) . . . ? C4 C5 H5a 109.2 . . . no C4 C5 H5b 108.9 . . . no C6 C5 H5a 109.2 . . . no C6 C5 H5b 109.0 . . . no H5a C5 H5b 109.4 . . . no C1 C6 C5 120(1) . . . ? C1 C6 C7 86.5(8) . . . ? C1 C6 H6 108.0 . . . no C5 C6 C7 123(1) . . . ? C5 C6 H6 108.2 . . . no C7 C6 H6 108.2 . . . no C6 C7 C8 89.8(9) . . . ? C6 C7 H7b 114.1 . . . no C6 C7 H7a 114.2 . . . no C8 C7 H7b 114.1 . . . no C8 C7 H7a 114.1 . . . no H7b C7 H7a 109.6 . . . no S1 C8 C1 111.6(8) . . . ? S1 C8 C7 113.8(8) . . . ? S1 C8 H8 113.7 . . . no C1 C8 C7 87.7(8) . . . ? C1 C8 H8 113.7 . . . no C7 C8 H8 113.7 . . . no S1 C9 C10 119(1) . . . ? S1 C9 C14 120.7(9) . . . ? C10 C9 C14 120(1) . . . ? C9 C10 C11 121(1) . . . ? C9 C10 H10 119.4 . . . no C11 C10 H10 119.5 . . . no C10 C11 C12 118(1) . . . ? C10 C11 H11 121.1 . . . no C12 C11 H11 120.9 . . . no C11 C12 C13 120(1) . . . ? C11 C12 H12 119.8 . . . no C13 C12 H12 119.8 . . . no C12 C13 C14 122(1) . . . ? C12 C13 H13 119.1 . . . no C14 C13 H13 119.2 . . . no C9 C14 C13 118(1) . . . ? C9 C14 H14 120.9 . . . no C13 C14 H14 120.9 . . . no O3 C15 C16 111.7(9) . . . ? O3 C15 C20 115(1) . . . ? O3 C15 C22 118(1) . . . ? C16 C15 C20 112(1) . . . ? C16 C15 C22 109.7(9) . . . ? C20 C15 C22 88.1(8) . . . ? C15 C16 C17 112(1) . . . ? C15 C16 H16a 108.8 . . . no C15 C16 H16b 108.8 . . . no C17 C16 H16a 108.6 . . . no C17 C16 H16b 108.7 . . . no H16a C16 H16b 109.5 . . . no C16 C17 C18 111(1) . . . ? C16 C17 H17a 109.1 . . . no C16 C17 H17b 109.2 . . . no C18 C17 H17a 109.2 . . . no C18 C17 H17b 109.2 . . . no H17a C17 H17b 109.6 . . . no C17 C18 C19 111(1) . . . ? C17 C18 H18a 109.0 . . . no C17 C18 H18b 109.0 . . . no C19 C18 H18a 109.2 . . . no C19 C18 H18b 109.3 . . . no H18a C18 H18b 109.5 . . . no C18 C19 C20 112(1) . . . ? C18 C19 H19a 108.9 . . . no C18 C19 H19b 108.8 . . . no C20 C19 H19a 108.9 . . . no C20 C19 H19b 108.9 . . . no H19a C19 H19b 109.6 . . . no C15 C20 C19 118(1) . . . ? C15 C20 C21 89.6(8) . . . ? C15 C20 H20 107.4 . . . no C19 C20 C21 125(1) . . . ? C19 C20 H20 107.4 . . . no C21 C20 H20 107.5 . . . no C20 C21 C22 87.7(8) . . . ? C20 C21 H21b 114.5 . . . no C20 C21 H21a 114.5 . . . no C22 C21 H21b 114.6 . . . no C22 C21 H21a 114.6 . . . no H21b C21 H21a 109.5 . . . no S2 C22 C15 111.0(8) . . . ? S2 C22 C21 113.9(8) . . . ? S2 C22 H22 113.9 . . . no C15 C22 C21 87.7(8) . . . ? C15 C22 H22 113.8 . . . no C21 C22 H22 113.9 . . . no S2 C23 C24 122(1) . . . ? S2 C23 C28 119(1) . . . ? C24 C23 C28 119(1) . . . ? C23 C24 C25 122(1) . . . ? C23 C24 H24 119.1 . . . no C25 C24 H24 119.2 . . . no C24 C25 C26 119(1) . . . ? C24 C25 H25 120.8 . . . no C26 C25 H25 120.3 . . . no C25 C26 C27 120(1) . . . ? C25 C26 H26 120.0 . . . no C27 C26 H26 119.7 . . . no C26 C27 C28 121(1) . . . ? C26 C27 H27 119.2 . . . no C28 C27 H27 119.4 . . . no C23 C28 C27 119(1) . . . ? C23 C28 H28 120.7 . . . no C27 C28 H28 120.7 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 H19b 2.9319 . 2_646 no S2 C13 3.57(1) . . no O1 H21b 2.7959 . 2_646 no O1 O4 2.87(1) . 3_666 no O1 H24 3.0023 . 2_646 no O1 O3 3.02(1) . 3_666 no O1 C24 3.43(1) . 2_646 no O1 C25 3.56(2) . 2_646 no O2 H16b 2.7457 . 3_666 no O2 O3 2.79(1) . 3_666 no O2 H19b 2.8165 . 2_646 no O2 H17a 2.8628 . 3_666 no O2 H26 2.9897 . 2_647 no O2 C16 3.34(1) . 3_666 no O2 C17 3.48(1) . 3_666 no O3 H2a 2.5812 . . no O3 H8 2.8531 . . no O3 C2 3.47(1) . . no O4 H2b 2.7501 . 3_666 no O4 H25 2.9051 . 4_465 no O4 H3a 3.0040 . 3_666 no O4 C2 3.39(1) . 3_666 no O4 C3 3.57(2) . 3_666 no O4 C14 3.59(1) . . no C19 H27 2.9833 . 1_554 no C26 H17a 2.9175 . 4_566 no C27 H12 3.0125 . 4_465 no H2b H14 2.5567 . 3_666 no H3b H26 2.4420 . 4_464 no H5b H13 2.6587 . 1_554 no H6 H10 2.6635 . 3_766 no H7b H16a 2.6792 . 4_565 no H7a H20 2.6697 . . no H16b H20 2.5588 . 4_465 no H17a H26 2.6561 . 4_464 no H19b H27 2.5027 . 1_554 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag S1 C8 C1 O1 . . . . 20(1) no S1 C8 C1 C2 . . . . 151.5(8) no S1 C8 C1 C6 . . . . -94.6(8) no S1 C8 C7 C6 . . . . 92.6(9) no S1 C9 C10 C11 . . . . -180(1) no S1 C9 C14 C13 . . . . 178(1) no S2 C22 C15 O3 . . . . 22(1) no S2 C22 C15 C16 . . . . 151.7(8) no S2 C22 C15 C20 . . . . -95.2(8) no S2 C22 C21 C20 . . . . 92.6(8) no S2 C23 C24 C25 . . . . 179(1) no S2 C23 C28 C27 . . . . -179(1) no O1 C1 C2 C3 . . . . -82(1) no O1 C1 C6 C5 . . . . 93(1) no O1 C1 C6 C7 . . . . -140(1) no O1 C1 C8 C7 . . . . 135(1) no O2 S1 C8 C1 . . . . -85.0(8) no O2 S1 C8 C7 . . . . 177.7(8) no O2 S1 C9 C10 . . . . 148(1) no O2 S1 C9 C14 . . . . -29(1) no O3 C15 C16 C17 . . . . -85(1) no O3 C15 C20 C19 . . . . 90(1) no O3 C15 C20 C21 . . . . -140(1) no O3 C15 C22 C21 . . . . 137.2(9) no O4 S2 C22 C15 . . . . -85.1(8) no O4 S2 C22 C21 . . . . 177.9(8) no O4 S2 C23 C24 . . . . 159(1) no O4 S2 C23 C28 . . . . -20(1) no C1 C2 C3 C4 . . . . -61(1) no C1 C6 C5 C4 . . . . 36(2) no C1 C6 C7 C8 . . . . 20.1(9) no C1 C8 S1 C9 . . . . 166.8(7) no C1 C8 C7 C6 . . . . -20.0(9) no C2 C1 C6 C5 . . . . -34(2) no C2 C1 C6 C7 . . . . 93(1) no C2 C1 C8 C7 . . . . -94(1) no C2 C3 C4 C5 . . . . 63(1) no C3 C2 C1 C6 . . . . 45(1) no C3 C2 C1 C8 . . . . 143(1) no C3 C4 C5 C6 . . . . -50(2) no C4 C5 C6 C7 . . . . -71(2) no C5 C6 C1 C8 . . . . -147(1) no C5 C6 C7 C8 . . . . 145(1) no C6 C1 C8 C7 . . . . 20.2(9) no C7 C6 C1 C8 . . . . -19.7(9) no C7 C8 S1 C9 . . . . 69(1) no C8 S1 C9 C10 . . . . -104(1) no C8 S1 C9 C14 . . . . 79(1) no C9 C10 C11 C12 . . . . 5(2) no C9 C14 C13 C12 . . . . -3(2) no C10 C9 C14 C13 . . . . 2(2) no C10 C11 C12 C13 . . . . -6(2) no C11 C10 C9 C14 . . . . -3(2) no C11 C12 C13 C14 . . . . 5(2) no C15 C16 C17 C18 . . . . -58(1) no C15 C20 C19 C18 . . . . 43(2) no C15 C20 C21 C22 . . . . 19.8(9) no C15 C22 S2 C23 . . . . 166.6(8) no C15 C22 C21 C20 . . . . -19.5(9) no C16 C15 C20 C19 . . . . -39(2) no C16 C15 C20 C21 . . . . 91(1) no C16 C15 C22 C21 . . . . -94(1) no C16 C17 C18 C19 . . . . 61(2) no C17 C16 C15 C20 . . . . 46(1) no C17 C16 C15 C22 . . . . 143(1) no C17 C18 C19 C20 . . . . -52(2) no C18 C19 C20 C21 . . . . -69(2) no C19 C20 C15 C22 . . . . -150(1) no C19 C20 C21 C22 . . . . 145(1) no C20 C15 C22 C21 . . . . 19.6(9) no C21 C20 C15 C22 . . . . -19.8(9) no C21 C22 S2 C23 . . . . 69.5(9) no C22 S2 C23 C24 . . . . -94(1) no C22 S2 C23 C28 . . . . 87(1) no C23 C24 C25 C26 . . . . 2(2) no C23 C28 C27 C26 . . . . -1(2) no C24 C23 C28 C27 . . . . 2(2) no C24 C25 C26 C27 . . . . -0(2) no C25 C24 C23 C28 . . . . -3(2) no C25 C26 C27 C28 . . . . -0(2) no #------------------------------------------------------------------------------ #============================================================================== data__476wl20_64phenylC _database_code_CSD 170564 #============================================================================== _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan for Windows version 1.06 (MSC, 1997-2001)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan for Windows version 1.06 (MSC, 1997-2001)' _computing_publication_material 'teXsan for Windows version 1.06 (MSC, 1997-2001)' #------------------------------------------------------------------------------ _cell_length_a 12.774(2) _cell_length_b 9.135(2) _cell_length_c 11.388(2) _cell_angle_alpha 90 _cell_angle_beta 104.79(1) _cell_angle_gamma 90 _cell_volume 1284.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.8 _cell_measurement_theta_max 12.5 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y, -z' ' -x, -y, -z' '1/2+x,1/2-y, +z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 250.35 _chemical_formula_analytical ? _chemical_formula_sum 'C14 H18 O2 S ' _chemical_formula_moiety 'C14 H18 O2 S ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 536.00 _exptl_absorpt_coefficient_mu 0.239 _exptl_absorpt_correction_type none _exptl_special_details ; The scan width was (1.58+0.30tan\q)\% with an \w scan speed of 16\% per minute (up to 5 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #============================================================================== # EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 295.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 13.41 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 -1 1 1 -2 1 0 -2 0 _diffrn_reflns_number 2824 _reflns_number_total 2430 _reflns_number_gt 1726 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.05606 _diffrn_reflns_av_sigmaI/netI 0.042 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.02239 _diffrn_orient_matrix_UB_12 -0.08275 _diffrn_orient_matrix_UB_13 0.05854 _diffrn_orient_matrix_UB_21 -0.01255 _diffrn_orient_matrix_UB_22 0.06291 _diffrn_orient_matrix_UB_23 0.06699 _diffrn_orient_matrix_UB_31 -0.07679 _diffrn_orient_matrix_UB_32 -0.03436 _diffrn_orient_matrix_UB_33 -0.01832 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 56 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; H 0 72 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 8 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; S 0 4 0.110 0.124 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom S1 0.33287(4) 0.37203(5) -0.19140(4) 0.0439(1) 1.000 . Uani d ? O1 0.3684(1) 0.4974(1) 0.0512(1) 0.0465(4) 1.000 . Uani d ? O2 0.4501(1) 0.3722(2) -0.1922(1) 0.0588(5) 1.000 . Uani d ? C1 0.3588(1) 0.3433(2) 0.0605(2) 0.0343(5) 1.000 . Uani d ? C2 0.2901(2) 0.3033(2) 0.1466(2) 0.0483(6) 1.000 . Uani d ? C3 0.3562(2) 0.2814(3) 0.2763(2) 0.0579(7) 1.000 . Uani d ? C4 0.4371(2) 0.1573(2) 0.2813(2) 0.0551(6) 1.000 . Uani d ? C5 0.5176(2) 0.1977(2) 0.2089(2) 0.0476(6) 1.000 . Uani d ? C6 0.4644(1) 0.2509(2) 0.0813(2) 0.0373(5) 1.000 . Uani d ? C7 0.4024(2) 0.1458(2) -0.0196(2) 0.0478(6) 1.000 . Uani d ? C8 0.3167(1) 0.2646(2) -0.0640(2) 0.0376(5) 1.000 . Uani d ? C9 0.2691(1) 0.2454(2) -0.3084(2) 0.0399(5) 1.000 . Uani d ? C10 0.3308(2) 0.1642(2) -0.3670(2) 0.0535(6) 1.000 . Uani d ? C11 0.2797(2) 0.0744(3) -0.4626(2) 0.0638(8) 1.000 . Uani d ? C12 0.1689(2) 0.0676(3) -0.4996(2) 0.0608(7) 1.000 . Uani d ? C13 0.1082(2) 0.1490(3) -0.4403(2) 0.0582(7) 1.000 . Uani d ? C14 0.1576(2) 0.2380(2) -0.3445(2) 0.0513(6) 1.000 . Uani d ? H1 0.4322 0.5304 0.1130 0.038 1.000 . Uiso c ? H2b 0.2525 0.2150 0.1191 0.058 1.000 . Uiso c ? H2a 0.2394 0.3797 0.1455 0.058 1.000 . Uiso c ? H3b 0.3092 0.2576 0.3261 0.069 1.000 . Uiso c ? H3a 0.3941 0.3691 0.3049 0.069 1.000 . Uiso c ? H4b 0.3993 0.0712 0.2481 0.066 1.000 . Uiso c ? H4a 0.4749 0.1400 0.3635 0.066 1.000 . Uiso c ? H5b 0.5599 0.1138 0.2033 0.057 1.000 . Uiso c ? H5a 0.5632 0.2732 0.2510 0.057 1.000 . Uiso c ? H6 0.5161 0.3041 0.0516 0.045 1.000 . Uiso c ? H7a 0.4414 0.1192 -0.0771 0.057 1.000 . Uiso c ? H7b 0.3756 0.0601 0.0100 0.057 1.000 . Uiso c ? H8 0.2451 0.2285 -0.0754 0.045 1.000 . Uiso c ? H10 0.4075 0.1694 -0.3423 0.064 1.000 . Uiso c ? H11 0.3219 0.0170 -0.5030 0.076 1.000 . Uiso c ? H12 0.1344 0.0069 -0.5660 0.073 1.000 . Uiso c ? H13 0.0314 0.1441 -0.4654 0.070 1.000 . Uiso c ? H14 0.1152 0.2939 -0.3034 0.061 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0457(3) 0.0410(3) 0.0400(3) -0.0092(2) 0.0017(2) -0.0000(2) O1 0.0451(8) 0.0318(7) 0.0547(8) -0.0007(6) -0.0020(6) -0.0033(6) O2 0.0457(8) 0.076(1) 0.0525(8) -0.0260(8) 0.0093(6) -0.0066(8) C1 0.0313(9) 0.0312(9) 0.038(1) -0.0010(8) 0.0040(7) -0.0005(8) C2 0.038(1) 0.056(1) 0.051(1) 0.0054(9) 0.0138(9) 0.004(1) C3 0.060(1) 0.071(2) 0.047(1) 0.001(1) 0.021(1) 0.002(1) C4 0.061(1) 0.057(1) 0.043(1) 0.003(1) 0.007(1) 0.010(1) C5 0.043(1) 0.045(1) 0.049(1) 0.0049(9) 0.0025(9) -0.001(1) C6 0.0337(9) 0.038(1) 0.040(1) 0.0015(8) 0.0074(8) -0.0018(8) C7 0.060(1) 0.037(1) 0.042(1) 0.006(1) 0.0069(9) -0.0028(9) C8 0.034(1) 0.037(1) 0.039(1) -0.0069(8) 0.0030(8) 0.0001(8) C9 0.043(1) 0.038(1) 0.034(1) -0.0042(9) 0.0026(8) 0.0026(8) C10 0.046(1) 0.064(1) 0.051(1) -0.003(1) 0.013(1) -0.002(1) C11 0.079(2) 0.067(2) 0.050(1) -0.004(1) 0.025(1) -0.014(1) C12 0.080(2) 0.059(1) 0.039(1) -0.017(1) 0.007(1) -0.006(1) C13 0.049(1) 0.062(1) 0.053(1) -0.008(1) -0.006(1) -0.006(1) C14 0.044(1) 0.050(1) 0.054(1) 0.002(1) 0.002(1) -0.007(1) #============================================================================== # REFINEMENT DATA _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00015|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.0000102(3) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1726 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_all 0.0570 _refine_ls_wR_factor_ref 0.0550 _refine_ls_goodness_of_fit_all 2.004 _refine_ls_goodness_of_fit_ref 2.240 _refine_ls_shift/su_max 0.0500 _refine_ls_shift/su_mean 0.0047 _refine_diff_density_min -0.24 _refine_diff_density_max 0.23 #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.500(2) . . ? S1 C8 1.807(3) . . ? S1 C9 1.795(3) . . ? O1 C1 1.419(3) . . ? O1 H1 0.98 . . no C1 C2 1.519(4) . . ? C1 C6 1.557(4) . . ? C1 C8 1.557(3) . . ? C2 C3 1.515(4) . . ? C2 H2b 0.95 . . no C2 H2a 0.95 . . no C3 C4 1.525(4) . . ? C3 H3b 0.95 . . no C3 H3a 0.95 . . no C4 C5 1.518(4) . . ? C4 H4b 0.95 . . no C4 H4a 0.95 . . no C5 C6 1.518(4) . . ? C5 H5b 0.95 . . no C5 H5a 0.95 . . no C6 C7 1.551(4) . . ? C6 H6 0.95 . . no C7 C8 1.532(4) . . ? C7 H7a 0.95 . . no C7 H7b 0.95 . . no C8 H8 0.95 . . no C9 C10 1.373(4) . . ? C9 C14 1.379(4) . . ? C10 C11 1.386(4) . . ? C10 H10 0.95 . . no C11 C12 1.371(5) . . ? C11 H11 0.95 . . no C12 C13 1.371(5) . . ? C12 H12 0.95 . . no C13 C14 1.378(4) . . ? C13 H13 0.95 . . no C14 H14 0.95 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 C8 108.9(1) . . . ? O2 S1 C9 105.1(1) . . . ? C8 S1 C9 97.1(1) . . . ? C1 O1 H1 109.0 . . . no O1 C1 C2 111.2(2) . . . ? O1 C1 C6 117.4(2) . . . ? O1 C1 C8 114.0(2) . . . ? C2 C1 C6 113.1(2) . . . ? C2 C1 C8 110.8(2) . . . ? C6 C1 C8 88.4(2) . . . ? C1 C2 C3 113.0(2) . . . ? C1 C2 H2b 108.6 . . . no C1 C2 H2a 108.6 . . . no C3 C2 H2b 108.6 . . . no C3 C2 H2a 108.6 . . . no H2b C2 H2a 109.5 . . . no C2 C3 C4 109.8(3) . . . ? C2 C3 H3b 109.4 . . . no C2 C3 H3a 109.4 . . . no C4 C3 H3b 109.4 . . . no C4 C3 H3a 109.4 . . . no H3b C3 H3a 109.4 . . . no C3 C4 C5 110.2(3) . . . ? C3 C4 H4b 109.3 . . . no C3 C4 H4a 109.3 . . . no C5 C4 H4b 109.3 . . . no C5 C4 H4a 109.3 . . . no H4b C4 H4a 109.5 . . . no C4 C5 C6 113.5(2) . . . ? C4 C5 H5b 108.5 . . . no C4 C5 H5a 108.5 . . . no C6 C5 H5b 108.5 . . . no C6 C5 H5a 108.5 . . . no H5b C5 H5a 109.5 . . . no C1 C6 C5 118.5(2) . . . ? C1 C6 C7 87.9(2) . . . ? C1 C6 H6 108.9 . . . no C5 C6 C7 122.0(2) . . . ? C5 C6 H6 108.9 . . . no C7 C6 H6 108.8 . . . no C6 C7 C8 89.6(2) . . . ? C6 C7 H7a 114.2 . . . no C6 C7 H7b 114.2 . . . no C8 C7 H7a 114.2 . . . no C8 C7 H7b 114.2 . . . no H7a C7 H7b 109.5 . . . no S1 C8 C1 113.3(2) . . . ? S1 C8 C7 115.6(2) . . . ? S1 C8 H8 112.4 . . . no C1 C8 C7 88.6(2) . . . ? C1 C8 H8 112.4 . . . no C7 C8 H8 112.4 . . . no S1 C9 C10 120.1(2) . . . ? S1 C9 C14 119.4(2) . . . ? C10 C9 C14 120.4(3) . . . ? C9 C10 C11 119.2(3) . . . ? C9 C10 H10 120.4 . . . no C11 C10 H10 120.4 . . . no C10 C11 C12 120.6(3) . . . ? C10 C11 H11 119.7 . . . no C12 C11 H11 119.7 . . . no C11 C12 C13 119.6(3) . . . ? C11 C12 H12 120.2 . . . no C13 C12 H12 120.2 . . . no C12 C13 C14 120.5(3) . . . ? C12 C13 H13 119.8 . . . no C14 C13 H13 119.7 . . . no C9 C14 C13 119.7(3) . . . ? C9 C14 H14 120.2 . . . no C13 C14 H14 120.2 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 H1 3.0379 . 3_665 no O1 H8 2.6154 . 2 no O1 O2 2.733(3) . 3_665 no O1 H6 2.7770 . 3_665 no O1 H2b 2.9278 . 2 no O1 C8 3.428(3) . 2 no O2 H1 1.7818 . 3_665 no O2 H12 2.9569 . 2_554 no C7 C7 3.599(6) . 3_655 no C11 H3b 3.0323 . 1_554 no C13 H3a 2.9894 . 2_545 no H1 H6 2.6194 . 3_665 no H2a H5b 2.5419 . 4_455 no H2a H7b 2.5845 . 2 no H4b H14 2.6283 . 2_545 no H5b H7a 2.5655 . 3_655 no H10 H14 2.5968 . 4 no H12 H13 2.6274 . 3_554 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag S1 C8 C1 O1 . . . . 19.7(3) no S1 C8 C1 C2 . . . . 146.1(2) no S1 C8 C1 C6 . . . . -99.8(2) no S1 C8 C7 C6 . . . . 97.7(2) no S1 C9 C10 C11 . . . . -175.7(2) no S1 C9 C14 C13 . . . . 175.2(2) no O1 C1 C2 C3 . . . . -91.6(3) no O1 C1 C6 C5 . . . . 100.5(3) no O1 C1 C6 C7 . . . . -133.8(2) no O1 C1 C8 C7 . . . . 137.1(2) no O2 S1 C8 C1 . . . . 74.2(2) no O2 S1 C8 C7 . . . . -26.0(2) no O2 S1 C9 C10 . . . . 6.1(3) no O2 S1 C9 C14 . . . . -169.4(2) no C1 C2 C3 C4 . . . . -60.5(4) no C1 C6 C5 C4 . . . . 35.5(4) no C1 C6 C7 C8 . . . . 17.7(2) no C1 C8 S1 C9 . . . . -177.1(2) no C1 C8 C7 C6 . . . . -17.7(2) no C2 C1 C6 C5 . . . . -31.1(3) no C2 C1 C6 C7 . . . . 94.6(2) no C2 C1 C8 C7 . . . . -96.6(2) no C2 C3 C4 C5 . . . . 63.7(3) no C3 C2 C1 C6 . . . . 43.0(3) no C3 C2 C1 C8 . . . . 140.5(3) no C3 C4 C5 C6 . . . . -50.8(3) no C4 C5 C6 C7 . . . . -71.4(3) no C5 C6 C1 C8 . . . . -143.1(2) no C5 C6 C7 C8 . . . . 140.4(2) no C6 C1 C8 C7 . . . . 17.6(2) no C7 C6 C1 C8 . . . . -17.4(2) no C7 C8 S1 C9 . . . . 82.7(2) no C8 S1 C9 C10 . . . . -105.7(3) no C8 S1 C9 C14 . . . . 78.7(2) no C9 C10 C11 C12 . . . . 0.8(5) no C9 C14 C13 C12 . . . . 0.2(5) no C10 C9 C14 C13 . . . . -0.4(5) no C10 C11 C12 C13 . . . . -0.9(5) no C11 C10 C9 C14 . . . . -0.1(5) no C11 C12 C13 C14 . . . . 0.4(5) no #------------------------------------------------------------------------------