Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'John Michael Brown' _publ_contact_author_address ; Dyson Perrins Laboratory University of Oxford South Parks Road OXFORD OX1 3QY UNITED KINGDO ; _publ_contact_author_email JOHN.BROWN@CHEMISTRY.OXFORD.AC.UK _publ_section_title ; Sequential ortho-lithiations; the sulfoxide group as a relay to enable meta-substitution ; loop_ _publ_author_name 'J. Brown' 'Malcolm Berry' 'Jonathan P. Flemming' data_arc794 _database_code_depnum_ccdc_archive 'CCDC 665873' #================================================ #============ # Diffractometer details #================================================ #============ _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #================================================ #============ # General computing #================================================ #============ _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, ; 2-tert-butylsulfinyl-3-methoxyphenylmethanol ; _chemical_melting_point '123-6 deg C' _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed #================================================ #============ _cell_length_a 8.5196(2) _cell_angle_alpha 90 _cell_length_b 11.9778(3) _cell_angle_beta 90.0140(15) _cell_length_c 11.9934(3) _cell_angle_gamma 90 _cell_volume 1223.88(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'S ' 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum 'C12 H18 O3 S1' _chemical_formula_moiety 'C12 H18 O3 S1' _chemical_compound_source ; synthesis as described in manuscriptCCDC ; _chemical_formula_weight 242.34 _cell_measurement_reflns_used 13716 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' fragment ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.26 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.34 _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.255 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) Wed Oct 31 17:30:57 2007 Page 5 enCIFer: arc794.cif ; _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.94 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 13716 _reflns_number_total 2761 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_theta_min 5.357 _diffrn_reflns_theta_max 27.458 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.458 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _refine_diff_density_min -0.31 _refine_diff_density_max 0.29 _refine_ls_number_reflns 2215 _refine_ls_number_restraints 0 _refine_ls_number_parameters 149 #_refine_ls_R_factor_ref 0.0308 _refine_ls_wR_factor_ref 0.0368 _refine_ls_goodness_of_fit_ref 1.0472 #_reflns_number_all 2761 _refine_ls_R_factor_all 0.0417 _refine_ls_wR_factor_all 0.0439 # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 2215 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_gt 0.0368 _refine_ls_shift/su_max 0.015332 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 2.85 -0.371 2.02 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type S1 S 0.18404(4) 0.62316(2) 0.76567(2) 0.0162 1.0000 Uani O1 O 0.33535(11) 0.58947(9) 0.82226(8) 0.0246 1.0000 Uani C1 C 0.08243(15) 0.48957(10) 0.73136(10) 0.0181 1.0000 Uani C2 C 0.03745(17) 0.44441(12) 0.84676(12) 0.0255 1.0000 Uani C3 C 0.19298(16) 0.40972(11) 0.67146(12) 0.0229 1.0000 Uani C4 C -0.06325(16) 0.51398(11) 0.66187(11) 0.0225 1.0000 Uani C5 C 0.23041(15) 0.67657(10) 0.62896(10) 0.0168 1.0000 Uani C6 C 0.11750(15) 0.75020(11) 0.58533(11) 0.0190 1.0000 Uani C7 C 0.13799(16) 0.79858(12) 0.48062(11) 0.0240 1.0000 Uani C8 C 0.27396(17) 0.77511(12) 0.42141(11) 0.0250 1.0000 Uani C9 C 0.38954(16) 0.70735(12) 0.46634(11) 0.0223 1.0000 Uani C10 C 0.37098(14) 0.65750(10) 0.57060(10) 0.0175 1.0000 Uani C11 C 0.50846(16) 0.59290(12) 0.61695(11) 0.0232 1.0000 Uani O2 O 0.58484(12) 0.65282(10) 0.70496(9) 0.0322 1.0000 Uani O3 O -0.00983(11) 0.76943(9) 0.65152(9) 0.0267 1.0000 Uani C12 C -0.1194(2) 0.85341(16) 0.61755(16) 0.0426 1.0000 Uani H1 H 0.502(3) 0.640(2) 0.769(2) 0.075(8) 1.0000 Uiso H21 H -0.0187 0.3716 0.8381 0.0306 1.0000 Uiso H22 H -0.0327 0.4992 0.8851 0.0306 1.0000 Uiso H23 H 0.1345 0.4330 0.8922 0.0306 1.0000 Uiso H31 H 0.1362 0.3388 0.6539 0.0275 1.0000 Uiso H32 H 0.2850 0.3930 0.7205 0.0275 1.0000 Uiso H33 H 0.2304 0.4449 0.6007 0.0275 1.0000 Uiso H41 H -0.1177 0.4423 0.6435 0.0270 1.0000 Uiso H42 H -0.1359 0.5632 0.7052 0.0270 1.0000 Uiso H43 H -0.0318 0.5525 0.5913 0.0270 1.0000 Uiso H71 H 0.0562 0.8493 0.4488 0.0288 1.0000 Uiso H81 H 0.2887 0.8075 0.3453 0.0300 1.0000 Uiso H91 H 0.4882 0.6939 0.4232 0.0268 1.0000 Uiso H111 H 0.5857 0.5791 0.5557 0.0278 1.0000 Uiso H112 H 0.4699 0.5199 0.6467 0.0278 1.0000 Uiso H121 H -0.2062 0.8584 0.6735 0.0512 1.0000 Uiso H122 H -0.0647 0.9271 0.6124 0.0512 1.0000 Uiso H123 H -0.1641 0.8334 0.5431 0.0512 1.0000 Uiso 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 0.01831(16) 0.01627(15) 0.01415(15) -0.00064(11) 0.00030(10) 0.00031(11) O1 0.0224(5) 0.0310(5) 0.0203(5) 0.0027(4) -0.0087(4) -0.0016(4) C1 0.0180(6) 0.0163(5) 0.0200(6) 0.0008(5) 0.0014(4) -0.0005(5) C2 0.0264(7) 0.0246(7) 0.0255(7) 0.0069(5) 0.0043(5) -0.0004(5) C3 0.0236(6) 0.0164(6) 0.0287(7) -0.0017(5) 0.0027(5) 0.0013(5) C4 0.0194(6) 0.0229(6) 0.0253(6) -0.0027(5) -0.0033(5) -0.0009(5) C5 0.0182(6) 0.0152(6) 0.0171(6) -0.0005(4) -0.0008(4) -0.0010(4) C6 0.0180(6) 0.0173(6) 0.0217(6) 0.0006(5) 0.0005(5) -0.0004(5) C7 0.0273(7) 0.0214(6) 0.0234(6) 0.0049(5) -0.0050(5) -0.0006(5) C8 0.0324(7) 0.0238(7) 0.0188(6) 0.0030(5) 0.0000(5) -0.0054(5) C9 0.0232(6) 0.0240(6) 0.0197(6) -0.0030(5) 0.0048(5) -0.0049(5) C10 0.0172(6) 0.0168(6) 0.0183(6) -0.0032(5) -0.0009(5) -0.0008(5) C11 0.0195(6) 0.0259(7) 0.0242(6) -0.0040(5) -0.0003(5) 0.0043(5) O2 0.0221(5) 0.0413(6) 0.0332(6) -0.0073(5) -0.0054(4) -0.0006(4) O3 0.0204(5) 0.0279(5) 0.0317(5) 0.0083(4) 0.0053(4) 0.0097(4) C12 0.0328(8) 0.0480(10) 0.0472(10) 0.0123(8) 0.0052(7) 0.0244(8) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 . O1 . 1.5116(10) yes S1 . C1 . 1.8652(13) yes S1 . C5 . 1.8038(13) yes C1 . C2 . 1.5347(18) yes C1 . C3 . 1.5227(18) yes C1 . C4 . 1.5232(18) yes C1 . C4 . 1.5232(18) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C2 . H23 . 1.000 no C3 . H31 . 1.000 no C3 . H32 . 1.000 no C3 . H33 . 1.000 no C4 . H41 . 1.000 no C4 . H42 . 1.000 no C4 . H43 . 1.000 no C5 . C6 . 1.4060(17) yes C5 . C10 . 1.4060(17) yes C6 . C7 . 1.3940(18) yes C6 . O3 . 1.3640(16) yes C7 . C8 . 1.388(2) yes C7 . H71 . 1.000 no C8 . C9 . 1.385(2) yes C8 . H81 . 1.000 no C9 . C10 . 1.3948(18) yes C9 . H91 . 1.000 no C10 . C11 . 1.5097(18) yes C11 . O2 . 1.4326(17) yes C11 . H111 . 1.000 no C11 . H112 . 1.000 no O2 . H1 . 1.05(3) no O3 . C12 . 1.4317(17) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C12 . H123 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 . S1 . C1 . 105.41(6) yes O1 . S1 . C5 . 108.41(6) yes C1 . S1 . C5 . 101.85(6) yes S1 . C1 . C2 . 102.68(9) yes S1 . C1 . C3 . 110.85(9) yes C2 . C1 . C3 . 111.02(11) yes S1 . C1 . C4 . 109.52(9) yes C2 . C1 . C4 . 110.94(11) yes C3 . C1 . C4 . 111.50(11) yes C1 . C2 . H21 . 109.467 no C1 . C2 . H22 . 109.467 no H21 . C2 . H22 . 109.476 no C1 . C2 . H23 . 109.467 no H21 . C2 . H23 . 109.476 no H22 . C2 . H23 . 109.476 no C1 . C3 . H31 . 109.467 no C1 . C3 . H31 . 109.467 no C1 . C3 . H32 . 109.467 no H31 . C3 . H32 . 109.476 no C1 . C3 . H33 . 109.467 no H31 . C3 . H33 . 109.476 no H32 . C3 . H33 . 109.476 no C1 . C4 . H41 . 109.467 no C1 . C4 . H42 . 109.467 no H41 . C4 . H42 . 109.476 no C1 . C4 . H43 . 109.467 no H41 . C4 . H43 . 109.475 no H42 . C4 . H43 . 109.476 no S1 . C5 . C6 . 114.26(10) yes S1 . C5 . C10 . 125.57(10) yes C6 . C5 . C10 . 119.96(12) yes C5 . C6 . C7 . 120.68(12) yes C5 . C6 . O3 . 115.69(11) yes C7 . C6 . O3 . 123.63(12) yes C6 . C7 . C8 . 118.78(12) yes C6 . C7 . H71 . 120.610 no C8 . C7 . H71 . 120.610 no C7 . C8 . C9 . 120.88(12) yes C7 . C8 . H81 . 119.562 no C9 . C8 . H81 . 119.562 no C8 . C9 . C10 . 121.26(12) yes C8 . C9 . H91 . 119.371 no C10 . C9 . H91 . 119.371 no C5 . C10 . C9 . 118.26(12) yes C5 . C10 . C11 . 124.11(12) yes C9 . C10 . C11 . 117.48(12) yes C10 . C11 . O2 . 111.51(11) yes C10 . C11 . H111 . 108.959 no O2 . C11 . H111 . 108.960 no C10 . C11 . H112 . 108.960 no O2 . C11 . H112 . 108.960 no H111 . C11 . H112 . 109.467 no C11 . O2 . H1 . 99.3(15) no C6 . O3 . C12 . 118.16(12) yes O3 . C12 . H121 . 109.467 no O3 . C12 . H122 . 109.467 no H121 . C12 . H122 . 109.476 no O3 . C12 . H123 . 109.467 no H121 . C12 . H123 . 109.476 no H122 . C12 . H123 . 109.476 no loop_ _geom_hbond_atom_site_label_d _geom_hbond_atom_site_label_h _geom_hbond_atom_site_label_a _geom_hbond_distance_dh _geom_hbond_distance_ha _geom_hbond_distance_da _geom_hbond_angle_dha _geom_hbond_publ_flag O2 H1 O1 1.05(3) 154(2) 1.67(3) 2.6597(15) yes _chemical_name_common 2-tert-butylsulfinyl-3-methoxyphenylmethanol #===================================================================== data_Carc899 _database_code_depnum_ccdc_archive 'CCDC 672147' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref #============================================================= _cell_length_a 8.8092(5) _cell_angle_alpha 90 _cell_length_b 11.8522(7) _cell_angle_beta 91.543(2) _cell_length_c 11.5256(7) _cell_angle_gamma 90 _cell_volume 1202.93(12) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'S ' 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C12 H16 O3 S1 ' _chemical_formula_moiety ' C12 H16 O3 S1 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 240.32 _cell_measurement_reflns_used 10760 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.03 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.259 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 10760 _reflns_number_total 2711 #2841 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.069 _diffrn_reflns_theta_min 5.205 _diffrn_reflns_theta_max 27.438 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.483 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _refine_diff_density_min -0.32 _refine_diff_density_max 0.26 _refine_ls_number_reflns 1673 _refine_ls_number_restraints 0 _refine_ls_number_parameters 145 #_refine_ls_R_factor_ref 0.0419 _refine_ls_wR_factor_ref 0.0478 _refine_ls_goodness_of_fit_ref 1.0871 #_reflns_number_all 2711 _refine_ls_R_factor_all 0.0859 _refine_ls_wR_factor_all 0.0673 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 1673 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_gt 0.0478 _refine_ls_shift/su_max 0.002884 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.81 0.498 1.49 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_disorder_assembly _atom_site_refinement_disorder_group _atom_site_attached_hydrogens S1 S 0.31595(7) 0.37658(4) 0.23455(5) 0.0288 1.0000 Uani . . . . . . O1 O 0.1622(2) 0.40886(16) 0.18470(15) 0.0425 1.0000 Uani . . . . . . C1 C 0.4150(3) 0.51192(18) 0.26865(18) 0.0280 1.0000 Uani . . . . . . C2 C 0.5605(3) 0.4875(2) 0.33862(19) 0.0321 1.0000 Uani . . . . . . C3 C 0.4523(3) 0.5572(2) 0.1485(2) 0.0393 1.0000 Uani . . . . . . C4 C 0.3109(3) 0.59206(19) 0.3319(2) 0.0337 1.0000 Uani . . . . . . C5 C 0.2857(2) 0.32181(18) 0.37776(19) 0.0272 1.0000 Uani . . . . . . C6 C 0.3973(2) 0.24820(18) 0.4228(2) 0.0288 1.0000 Uani . . . . . . C7 C 0.3818(3) 0.19961(19) 0.5316(2) 0.0338 1.0000 Uani . . . . . . C8 C 0.2522(3) 0.2206(2) 0.5928(2) 0.0379 1.0000 Uani . . . . . . C9 C 0.1363(3) 0.2869(2) 0.5461(2) 0.0369 1.0000 Uani . . . . . . C10 C 0.1517(3) 0.33810(19) 0.4379(2) 0.0320 1.0000 Uani . . . . . . C11 C 0.0201(3) 0.4047(2) 0.3927(2) 0.0421 1.0000 Uani . . . . . . O2 O -0.1078(3) 0.3779(2) 0.4134(3) 0.0836 1.0000 Uani . . . . . . O3 O 0.51726(18) 0.22846(14) 0.35285(15) 0.0363 1.0000 Uani . . . . . . C12 C 0.6241(3) 0.1428(2) 0.3882(3) 0.0512 1.0000 Uani . . . . . . H21 H 0.6138 0.5601 0.3570 0.0383 1.0000 Uiso . . . . . . H22 H 0.5349 0.4484 0.4124 0.0383 1.0000 Uiso . . . . . . H23 H 0.6281 0.4381 0.2923 0.0383 1.0000 Uiso . . . . . . H31 H 0.5065 0.6310 0.1568 0.0471 1.0000 Uiso . . . . . . H32 H 0.5186 0.5020 0.1082 0.0471 1.0000 Uiso . . . . . . H33 H 0.3560 0.5683 0.1018 0.0471 1.0000 Uiso . . . . . . H41 H 0.3661 0.6641 0.3494 0.0403 1.0000 Uiso . . . . . . H42 H 0.2791 0.5565 0.4061 0.0403 1.0000 Uiso . . . . . . H43 H 0.2190 0.6083 0.2818 0.0403 1.0000 Uiso . . . . . . H71 H 0.4636 0.1500 0.5651 0.0404 1.0000 Uiso . . . . . . H81 H 0.2419 0.1875 0.6720 0.0454 1.0000 Uiso . . . . . . H91 H 0.0411 0.2982 0.5901 0.0443 1.0000 Uiso . . . . . . H111 H 0.0383 0.4731 0.3442 0.0504 1.0000 Uiso . . . . . . H121 H 0.7055 0.1371 0.3297 0.0615 1.0000 Uiso . . . . . . H122 H 0.6705 0.1630 0.4656 0.0615 1.0000 Uiso . . . . . . H123 H 0.5705 0.0687 0.3939 0.0615 1.0000 Uiso . . . . . . 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 0.0319(3) 0.0290(3) 0.0251(3) -0.0015(2) -0.00775(18) 0.0001(2) O1 0.0384(9) 0.0446(10) 0.0432(10) 0.0017(8) -0.0224(8) -0.0006(8) C1 0.0305(11) 0.0249(10) 0.0282(10) 0.0002(8) -0.0057(8) 0.0003(8) C2 0.0304(11) 0.0329(11) 0.0325(11) -0.0004(9) -0.0057(9) -0.0019(9) C3 0.0433(14) 0.0408(13) 0.0337(13) 0.0095(10) -0.0007(11) -0.0001(11) C4 0.0373(13) 0.0291(10) 0.0345(12) -0.0023(9) -0.0033(10) 0.0014(9) C5 0.0245(10) 0.0270(10) 0.0299(11) -0.0002(8) -0.0034(8) -0.0022(8) C6 0.0270(11) 0.0279(10) 0.0314(11) 0.0008(8) -0.0025(9) -0.0028(8) C7 0.0373(12) 0.0302(11) 0.0335(12) 0.0011(9) -0.0082(10) -0.0038(9) C8 0.0481(14) 0.0359(12) 0.0294(12) -0.0007(9) -0.0025(10) -0.0122(11) C9 0.0368(13) 0.0365(12) 0.0375(13) -0.0037(10) 0.0051(10) -0.0090(10) C10 0.0273(11) 0.0316(11) 0.0370(12) -0.0067(9) -0.0017(9) -0.0034(9) C11 0.0316(13) 0.0458(14) 0.0486(15) -0.0062(11) -0.0020(10) 0.0031(10) O2 0.0322(11) 0.100(2) 0.119(2) 0.0275(17) 0.0048(12) 0.0092(13) O3 0.0300(8) 0.0375(9) 0.0413(10) 0.0073(7) 0.0008(7) 0.0101(7) C12 0.0413(15) 0.0557(17) 0.0567(16) 0.0108(14) 0.0020(12) 0.0239(13) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 . O1 . 1.5059(17) yes S1 . C1 . 1.863(2) yes S1 . C5 . 1.800(2) yes C1 . C2 . 1.524(3) yes C1 . C3 . 1.530(3) yes C1 . C4 . 1.520(3) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C2 . H23 . 1.000 no C3 . H31 . 1.000 no C3 . H32 . 1.000 no C3 . H33 . 1.000 no C4 . H41 . 1.000 no C4 . H42 . 1.000 no C4 . H43 . 1.000 no C5 . C6 . 1.403(3) yes C5 . C10 . 1.398(3) yes C6 . C7 . 1.390(3) yes C6 . O3 . 1.367(3) yes C7 . C8 . 1.381(4) yes C7 . H71 . 1.000 no C8 . C9 . 1.386(4) yes C8 . H81 . 1.000 no C9 . C10 . 1.398(3) yes C9 . H91 . 1.000 no C10 . C11 . 1.485(3) yes C11 . O2 . 1.201(4) yes C11 . H111 . 1.000 no O3 . C12 . 1.435(3) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C12 . H123 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 . S1 . C1 . 105.84(10) yes O1 . S1 . C5 . 106.71(11) yes C1 . S1 . C5 . 101.37(10) yes S1 . C1 . C2 . 109.31(15) yes S1 . C1 . C3 . 102.82(15) yes C2 . C1 . C3 . 110.4(2) yes S1 . C1 . C4 . 110.75(16) yes C2 . C1 . C4 . 111.99(18) yes C3 . C1 . C4 . 111.23(19) yes C1 . C2 . H21 . 109.466 no C1 . C2 . H22 . 109.466 no H21 . C2 . H22 . 109.476 no C1 . C2 . H23 . 109.467 no H21 . C2 . H23 . 109.476 no H22 . C2 . H23 . 109.476 no C1 . C3 . H31 . 109.467 no C1 . C3 . H32 . 109.467 no H31 . C3 . H32 . 109.475 no C1 . C3 . H33 . 109.467 no H31 . C3 . H33 . 109.476 no H32 . C3 . H33 . 109.476 no C1 . C4 . H41 . 109.467 no C1 . C4 . H42 . 109.467 no H41 . C4 . H42 . 109.476 no C1 . C4 . H43 . 109.467 no H41 . C4 . H43 . 109.476 no H42 . C4 . H43 . 109.476 no S1 . C5 . C6 . 116.34(17) yes S1 . C5 . C10 . 123.53(17) yes C6 . C5 . C10 . 119.7(2) yes C5 . C6 . C7 . 120.4(2) yes C5 . C6 . O3 . 115.7(2) yes C7 . C6 . O3 . 123.9(2) yes C6 . C7 . C8 . 119.3(2) yes C6 . C7 . H71 . 120.350 no C8 . C7 . H71 . 120.350 no C7 . C8 . C9 . 120.9(2) yes C7 . C8 . H81 . 119.532 no C9 . C8 . H81 . 119.532 no C8 . C9 . C10 . 120.3(2) yes C8 . C9 . H91 . 119.844 no C10 . C9 . H91 . 119.844 no C5 . C10 . C9 . 119.1(2) yes C5 . C10 . C11 . 124.2(2) yes C9 . C10 . C11 . 116.7(2) yes C10 . C11 . O2 . 121.2(3) yes C10 . C11 . H111 . 119.408 no O2 . C11 . H111 . 119.408 no C6 . O3 . C12 . 117.7(2) yes O3 . C12 . H121 . 109.467 no O3 . C12 . H122 . 109.466 no H121 . C12 . H122 . 109.476 no O3 . C12 . H123 . 109.467 no H121 . C12 . H123 . 109.476 no H122 . C12 . H123 . 109.476 no # Attachment 'arc900ch.cif' #===================================================================== data_arc900 _database_code_depnum_ccdc_archive 'CCDC 672148' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref #============================================================= _cell_length_a 8.4450(3) _cell_angle_alpha 90 _cell_length_b 12.0343(4) _cell_angle_beta 91.0936(16) _cell_length_c 11.7417(4) _cell_angle_gamma 90 _cell_volume 1193.09(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'S ' 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C12 H18 O2 S1 ' _chemical_formula_moiety ' C12 H18 O2 S1 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 226.34 _cell_measurement_reflns_used 8955 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_max 0.28 _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.250 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 8955 _reflns_number_total 2702 #2830 unique reflcetions including absences _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_theta_min 5.118 _diffrn_reflns_theta_max 27.479 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.479 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _refine_diff_density_min -0.26 _refine_diff_density_max 0.25 _refine_ls_number_reflns 2132 _refine_ls_number_restraints 0 _refine_ls_number_parameters 136 #_refine_ls_R_factor_ref 0.0326 _refine_ls_wR_factor_ref 0.0442 _refine_ls_goodness_of_fit_ref 0.9915 #_reflns_number_all 2702 _refine_ls_R_factor_all 0.0446 _refine_ls_wR_factor_all 0.0494 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 2132 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_gt 0.0442 _refine_ls_shift/su_max 0.000394 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.09 0.537 0.709 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 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_occupancy _atom_site_adp_type S1 S 0.31522(4) 0.37442(3) 0.23368(3) 0.0198 1.0000 Uani O1 O 0.16389(14) 0.40533(11) 0.17331(10) 0.0319 1.0000 Uani C1 C 0.41494(17) 0.50846(11) 0.26956(12) 0.0193 1.0000 Uani C2 C 0.56466(18) 0.48595(13) 0.34059(13) 0.0241 1.0000 Uani C3 C 0.4567(2) 0.55538(14) 0.15272(14) 0.0288 1.0000 Uani C4 C 0.30217(19) 0.58581(13) 0.33128(14) 0.0254 1.0000 Uani C5 C 0.26987(17) 0.32239(11) 0.37364(12) 0.0189 1.0000 Uani C6 C 0.38514(17) 0.25116(12) 0.42180(12) 0.0207 1.0000 Uani C7 C 0.36517(19) 0.20477(13) 0.52934(13) 0.0253 1.0000 Uani C8 C 0.2259(2) 0.22724(13) 0.58618(13) 0.0276 1.0000 Uani C9 C 0.10773(19) 0.29211(13) 0.53662(14) 0.0269 1.0000 Uani C10 C 0.12672(18) 0.34037(12) 0.42931(13) 0.0226 1.0000 Uani C11 C -0.0136(2) 0.40227(16) 0.37881(16) 0.0341 1.0000 Uani O3 O 0.51492(13) 0.23179(10) 0.35699(10) 0.0283 1.0000 Uani C12 C 0.6132(2) 0.13927(17) 0.38786(17) 0.0402 1.0000 Uani H21 H 0.6179 0.5580 0.3597 0.0289 1.0000 Uiso H22 H 0.5360 0.4469 0.4125 0.0289 1.0000 Uiso H23 H 0.6382 0.4383 0.2961 0.0289 1.0000 Uiso H31 H 0.5116 0.6285 0.1627 0.0346 1.0000 Uiso H32 H 0.5283 0.5023 0.1131 0.0346 1.0000 Uiso H33 H 0.3576 0.5660 0.1060 0.0346 1.0000 Uiso H41 H 0.3576 0.6571 0.3498 0.0305 1.0000 Uiso H42 H 0.2673 0.5497 0.4033 0.0305 1.0000 Uiso H43 H 0.2076 0.6013 0.2812 0.0305 1.0000 Uiso H71 H 0.4490 0.1565 0.5647 0.0303 1.0000 Uiso H81 H 0.2107 0.1961 0.6642 0.0331 1.0000 Uiso H91 H 0.0071 0.3046 0.5783 0.0324 1.0000 Uiso H111 H -0.1010 0.4039 0.4351 0.0410 1.0000 Uiso H112 H 0.0185 0.4801 0.3602 0.0410 1.0000 Uiso H113 H -0.0512 0.3638 0.3078 0.0410 1.0000 Uiso H121 H 0.7034 0.1342 0.3342 0.0482 1.0000 Uiso H122 H 0.6554 0.1497 0.4673 0.0482 1.0000 Uiso H123 H 0.5495 0.0693 0.3837 0.0482 1.0000 Uiso 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 0.02379(19) 0.01964(18) 0.01577(18) -0.00108(12) -0.00170(12) -0.00046(13) O1 0.0298(6) 0.0375(6) 0.0279(6) 0.0034(5) -0.0143(5) -0.0041(5) C1 0.0200(6) 0.0184(6) 0.0194(6) 0.0008(5) -0.0007(5) 0.0006(5) C2 0.0239(7) 0.0228(7) 0.0257(7) -0.0022(6) -0.0035(5) -0.0004(6) C3 0.0331(8) 0.0283(7) 0.0252(8) 0.0082(6) 0.0039(6) -0.0001(6) C4 0.0269(7) 0.0205(7) 0.0289(8) -0.0017(6) 0.0013(6) 0.0035(6) C5 0.0212(7) 0.0167(6) 0.0186(6) -0.0008(5) -0.0003(5) -0.0006(5) C6 0.0205(6) 0.0182(6) 0.0233(7) -0.0002(5) 0.0006(5) -0.0011(5) C7 0.0302(8) 0.0211(7) 0.0244(7) 0.0038(6) -0.0034(6) -0.0012(6) C8 0.0379(9) 0.0239(7) 0.0210(7) 0.0020(6) 0.0022(6) -0.0062(6) C9 0.0288(8) 0.0247(7) 0.0275(8) -0.0022(6) 0.0075(6) -0.0046(6) C10 0.0219(7) 0.0200(7) 0.0259(7) -0.0020(5) 0.0015(5) -0.0008(5) C11 0.0258(8) 0.0380(9) 0.0386(9) -0.0007(7) 0.0028(7) 0.0053(7) O3 0.0244(5) 0.0273(6) 0.0334(6) 0.0074(4) 0.0062(4) 0.0091(4) C12 0.0376(10) 0.0427(10) 0.0403(10) 0.0074(8) 0.0027(8) 0.0221(8) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 . O1 . 1.4965(11) yes S1 . C1 . 1.8642(14) yes S1 . C5 . 1.8065(14) yes C1 . C2 . 1.5255(19) yes C1 . C3 . 1.531(2) yes C1 . C4 . 1.525(2) yes C2 . H21 . 1.000 no C2 . H22 . 1.000 no C2 . H23 . 1.000 no C3 . H31 . 1.000 no C3 . H32 . 1.000 no C3 . H33 . 1.000 no C4 . H41 . 1.000 no C4 . H42 . 1.000 no C4 . H43 . 1.000 no C5 . C6 . 1.407(2) yes C5 . C10 . 1.402(2) yes C6 . C7 . 1.394(2) yes C6 . O3 . 1.3662(18) yes C7 . C8 . 1.390(2) yes C7 . H71 . 1.000 no C8 . C9 . 1.386(2) yes C8 . H81 . 1.000 no C9 . C10 . 1.399(2) yes C9 . H91 . 1.000 no C10 . C11 . 1.512(2) yes C11 . H111 . 1.000 no C11 . H112 . 1.000 no C11 . H113 . 1.000 no O3 . C12 . 1.431(2) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C12 . H123 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 . S1 . C1 . 105.66(7) yes O1 . S1 . C5 . 108.85(7) yes C1 . S1 . C5 . 101.36(6) yes S1 . C1 . C2 . 109.64(10) yes S1 . C1 . C3 . 103.15(10) yes C2 . C1 . C3 . 110.64(12) yes S1 . C1 . C4 . 110.61(10) yes C2 . C1 . C4 . 111.55(12) yes C3 . C1 . C4 . 110.95(12) yes C1 . C2 . H21 . 109.467 no C1 . C2 . H22 . 109.467 no H21 . C2 . H22 . 109.476 no C1 . C2 . H23 . 109.467 no H21 . C2 . H23 . 109.476 no H22 . C2 . H23 . 109.476 no C1 . C3 . H31 . 109.467 no C1 . C3 . H32 . 109.467 no H31 . C3 . H32 . 109.476 no C1 . C3 . H33 . 109.467 no H31 . C3 . H33 . 109.476 no H32 . C3 . H33 . 109.476 no C1 . C4 . H41 . 109.467 no C1 . C4 . H42 . 109.467 no H41 . C4 . H42 . 109.476 no C1 . C4 . H43 . 109.467 no H41 . C4 . H43 . 109.476 no H42 . C4 . H43 . 109.476 no S1 . C5 . C6 . 114.81(10) yes S1 . C5 . C10 . 124.77(11) yes C6 . C5 . C10 . 120.17(13) yes C5 . C6 . C7 . 120.88(14) yes C5 . C6 . O3 . 115.86(13) yes C7 . C6 . O3 . 123.26(13) yes C6 . C7 . C8 . 118.37(14) yes C6 . C7 . H71 . 120.814 no C8 . C7 . H71 . 120.814 no C7 . C8 . C9 . 121.13(14) yes C7 . C8 . H81 . 119.434 no C9 . C8 . H81 . 119.434 no C8 . C9 . C10 . 121.18(14) yes C8 . C9 . H91 . 119.411 no C10 . C9 . H91 . 119.411 no C5 . C10 . C9 . 118.06(14) yes C5 . C10 . C11 . 124.74(14) yes C9 . C10 . C11 . 117.08(14) yes C10 . C11 . H111 . 109.467 no C10 . C11 . H112 . 109.467 no H111 . C11 . H112 . 109.476 no C10 . C11 . H113 . 109.467 no H111 . C11 . H113 . 109.476 no H112 . C11 . H113 . 109.476 no C6 . O3 . C12 . 117.34(13) yes O3 . C12 . H121 . 109.467 no O3 . C12 . H122 . 109.467 no H121 . C12 . H122 . 109.476 no O3 . C12 . H123 . 109.467 no H121 . C12 . H123 . 109.476 no H122 . C12 . H123 . 109.476 no