# Supplementary Material (ESI) 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 'Peter Langer' _publ_contact_author_address ; Institut fur Chemie, Abteilung fur Organische Chemie Universitat Rostock Albert-Einstein-Strasse 3a Rostock 18051 GERMANY ; _publ_contact_author_email PETER.LANGER@UNI-ROSTOCK.DE _publ_section_title ; One-Pot Synthesis of 6-(Thien-2-yl)- and 6-(Fur-2-yl)salicylates based on Regioselective [3+3] Cyclizations of 1,3-Bis(trimethyl-silyloxy)-1,3-butadienes ; loop_ _publ_author_name 'Peter Langer' 'Christine Fischer' 'Helmar Gorls' 'Ibrar Hussain' 'Abdolmajid Riahi' 'Alexander Villinger' ; M.A.Yawer ; data_av_ah230c1r _database_code_depnum_ccdc_archive 'CCDC 664610' _audit_author_name 'Villinger, A.' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; Methyl 4-(fur-2-yl)-6-trifluormethyl-salicylate ; _chemical_name_common 'Methyl 4-(fur-2-yl)-6-trifluormethyl-salicylate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H9 F3 O4' _chemical_formula_weight 286.20 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 2 1' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 13.851(3) _cell_length_b 4.8284(10) _cell_length_c 35.183(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2353.0(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1347 _cell_measurement_theta_min 6.001 _cell_measurement_theta_max 45.365 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.81 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8885 _exptl_absorpt_correction_T_max 0.9926 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9001 _diffrn_reflns_av_R_equivalents 0.0851 _diffrn_reflns_av_sigmaI/netI 0.0991 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 23.30 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 23.30 _diffrn_measured_fraction_theta_full 0.983 _reflns_number_total 3320 _reflns_number_gt 2318 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex v2.0-2' _computing_cell_refinement 'Bruker Apex v2.0-2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL-97 #============================================================================== # REFINEMENT DATA _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^)+(0.1079P)^2^+0.0000P] 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(3) _refine_ls_number_reflns 3320 _refine_ls_number_parameters 348 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1026 _refine_ls_R_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.1907 _refine_ls_wR_factor_gt 0.1693 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.687 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.100 #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 C1 C 0.4067(6) 0.1266(18) 0.3786(2) 0.0230(19) Uani 1 1 d . . . C2 C 0.4353(6) 0.189(2) 0.3412(3) 0.020(2) Uani 1 1 d . . . C3 C 0.3951(6) 0.3878(17) 0.3193(3) 0.029(2) Uani 1 1 d . . . H3 H 0.4200 0.4254 0.2946 0.034 Uiso 1 1 calc R . . C4 C 0.3164(5) 0.5368(16) 0.3333(2) 0.0198(17) Uani 1 1 d . . . C5 C 0.2790(6) 0.4711(16) 0.3693(2) 0.0254(19) Uani 1 1 d . . . H5 H 0.2228 0.5624 0.3784 0.030 Uiso 1 1 calc R . . C6 C 0.3244(7) 0.2723(14) 0.3918(3) 0.0172(9) Uani 1 1 d . . . C7 C 0.2735(7) 0.2147(17) 0.4303(4) 0.020(3) Uani 1 1 d . . . C8 C 0.4655(6) -0.0736(16) 0.4001(2) 0.0237(19) Uani 1 1 d . . . O8 O 0.4510(6) 0.2112(13) 0.2134(2) 0.0258(17) Uani 1 1 d . . . C9 C 0.5070(9) -0.2686(18) 0.4596(4) 0.0329(11) Uani 1 1 d . . . H9A H 0.5042 -0.4536 0.4482 0.049 Uiso 1 1 calc R . . H9B H 0.4809 -0.2761 0.4855 0.049 Uiso 1 1 calc R . . H9C H 0.5741 -0.2052 0.4604 0.049 Uiso 1 1 calc R . . C10 C 0.2689(7) 0.7439(14) 0.3103(4) 0.0178(9) Uani 1 1 d . . . C11 C 0.1916(6) 0.9121(17) 0.3164(2) 0.0247(19) Uani 1 1 d . . . H11 H 0.1531 0.9196 0.3388 0.030 Uiso 1 1 calc R . . C12 C 0.1797(6) 1.0720(18) 0.2836(2) 0.033(2) Uani 1 1 d . . . H12 H 0.1319 1.2102 0.2796 0.039 Uiso 1 1 calc R . . C13 C 0.2467(6) 0.9960(18) 0.2592(2) 0.029(2) Uani 1 1 d . . . H13 H 0.2554 1.0697 0.2344 0.034 Uiso 1 1 calc R . . O1 O 0.5127(4) 0.0521(12) 0.32480(16) 0.0298(14) Uani 1 1 d . . . H1 H 0.5443 -0.0303 0.3417 0.045 Uiso 1 1 calc R . . O2 O 0.5288(5) -0.2256(13) 0.3859(3) 0.030(2) Uani 1 1 d . . . O3 O 0.4498(4) -0.0767(13) 0.43688(17) 0.0364(15) Uani 1 1 d . . . O4 O 0.3025(6) 0.7898(13) 0.2758(3) 0.032(2) Uani 1 1 d . . . F1 F 0.1837(4) 0.3148(12) 0.43010(19) 0.0408(15) Uani 1 1 d . . . F2 F 0.3177(5) 0.2943(11) 0.45906(19) 0.0357(16) Uani 1 1 d . . . F3 F 0.2589(3) -0.0691(9) 0.43375(13) 0.0327(11) Uani 1 1 d . . . C14 C 0.3478(5) 0.8739(15) 0.1084(2) 0.0170(17) Uani 1 1 d . . . C15 C 0.3142(7) 0.815(2) 0.1451(3) 0.026(2) Uani 1 1 d . . . C16 C 0.3603(5) 0.6070(14) 0.1671(2) 0.0198(18) Uani 1 1 d . . . H16 H 0.3359 0.5661 0.1917 0.024 Uiso 1 1 calc R . . C17 C 0.4388(6) 0.4638(16) 0.1540(2) 0.0229(18) Uani 1 1 d . . . C18 C 0.4736(6) 0.5324(16) 0.1183(2) 0.0219(19) Uani 1 1 d . . . H18 H 0.5289 0.4371 0.1092 0.026 Uiso 1 1 calc R . . C19 C 0.4326(7) 0.7302(14) 0.0955(3) 0.0172(9) Uani 1 1 d . . . C20 C 0.4802(8) 0.792(2) 0.0603(4) 0.032(3) Uani 1 1 d . . . C21 C 0.2891(6) 1.0700(17) 0.0864(2) 0.0214(18) Uani 1 1 d . . . C22 C 0.2478(9) 1.2625(18) 0.0276(4) 0.0329(11) Uani 1 1 d . . . H22A H 0.1790 1.2388 0.0332 0.049 Uiso 1 1 calc R . . H22B H 0.2591 1.2300 0.0005 0.049 Uiso 1 1 calc R . . H22C H 0.2676 1.4515 0.0341 0.049 Uiso 1 1 calc R . . C23 C 0.4877(7) 0.2547(14) 0.1767(4) 0.0178(9) Uani 1 1 d . . . C24 C 0.5626(5) 0.0849(15) 0.1696(2) 0.0210(17) Uani 1 1 d . . . H24 H 0.5992 0.0762 0.1468 0.025 Uiso 1 1 calc R . . C25 C 0.5766(6) -0.0792(15) 0.2028(2) 0.029(2) Uani 1 1 d . . . H25 H 0.6246 -0.2171 0.2064 0.034 Uiso 1 1 calc R . . C26 C 0.5087(7) -0.0010(18) 0.2280(2) 0.034(2) Uani 1 1 d . . . H26 H 0.5010 -0.0801 0.2525 0.041 Uiso 1 1 calc R . . O5 O 0.2419(4) 0.9504(12) 0.16219(17) 0.0349(15) Uani 1 1 d . . . H5B H 0.2194 1.0701 0.1473 0.052 Uiso 1 1 calc R . . O6 O 0.2318(5) 1.2304(11) 0.1012(2) 0.024(2) Uani 1 1 d . . . O7 O 0.3032(4) 1.0680(12) 0.04954(16) 0.0301(14) Uani 1 1 d . . . F4 F 0.5701(4) 0.6800(12) 0.05691(18) 0.0428(15) Uani 1 1 d . . . F5 F 0.4952(3) 1.0635(9) 0.05300(14) 0.0332(11) Uani 1 1 d . . . F6 F 0.4342(5) 0.6951(12) 0.02744(19) 0.0381(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.014(4) 0.029(5) 0.026(5) -0.006(3) -0.007(3) -0.004(3) C2 0.018(5) 0.035(4) 0.007(5) -0.003(4) 0.004(4) -0.011(4) C3 0.019(5) 0.037(6) 0.030(5) -0.010(4) 0.004(4) 0.005(4) C4 0.014(4) 0.020(4) 0.026(4) -0.001(3) 0.000(3) -0.004(3) C5 0.022(5) 0.027(5) 0.028(5) -0.004(4) 0.004(3) -0.004(4) C6 0.016(2) 0.014(2) 0.021(2) 0.0006(17) -0.0010(17) 0.000(2) C7 0.019(6) 0.020(5) 0.021(6) 0.013(4) 0.016(4) 0.005(4) C8 0.023(5) 0.022(5) 0.026(5) 0.002(4) -0.003(4) -0.002(4) O8 0.025(4) 0.036(4) 0.016(4) 0.010(3) 0.004(3) 0.000(3) C9 0.028(3) 0.045(3) 0.026(2) 0.011(2) -0.0073(18) 0.010(3) C10 0.017(2) 0.018(2) 0.019(2) -0.0024(18) 0.0022(17) -0.006(2) C11 0.018(4) 0.035(5) 0.022(4) 0.003(3) 0.007(3) -0.006(4) C12 0.018(5) 0.038(5) 0.041(5) -0.010(4) -0.005(4) -0.001(4) C13 0.028(5) 0.028(5) 0.030(4) 0.001(3) -0.005(4) 0.002(4) O1 0.031(4) 0.030(3) 0.029(3) 0.001(3) 0.005(3) 0.016(3) O2 0.009(4) 0.048(5) 0.035(5) -0.003(3) 0.000(3) 0.007(3) O3 0.038(4) 0.048(4) 0.023(3) 0.003(3) -0.005(3) 0.016(3) O4 0.026(4) 0.029(4) 0.042(5) -0.008(3) 0.001(4) 0.006(3) F1 0.028(4) 0.055(3) 0.040(3) 0.012(3) 0.016(3) 0.015(3) F2 0.052(4) 0.040(3) 0.015(3) -0.006(3) 0.004(3) 0.006(3) F3 0.041(3) 0.025(2) 0.033(3) 0.009(2) 0.010(2) -0.009(2) C14 0.018(4) 0.009(4) 0.024(5) 0.002(3) 0.004(3) 0.000(3) C15 0.013(5) 0.023(4) 0.042(7) -0.001(5) 0.008(4) 0.011(4) C16 0.025(5) 0.013(4) 0.021(4) 0.010(3) 0.002(4) -0.009(4) C17 0.022(5) 0.022(4) 0.024(4) -0.005(4) 0.000(3) -0.001(4) C18 0.022(5) 0.020(4) 0.024(4) -0.006(3) 0.000(3) 0.003(4) C19 0.016(2) 0.014(2) 0.021(2) 0.0006(17) -0.0010(17) 0.000(2) C20 0.029(7) 0.033(6) 0.035(7) -0.010(5) -0.009(5) 0.001(4) C21 0.017(4) 0.028(5) 0.020(4) -0.001(4) -0.002(3) -0.010(4) C22 0.028(3) 0.045(3) 0.026(2) 0.011(2) -0.0073(18) 0.010(3) C23 0.017(2) 0.018(2) 0.019(2) -0.0024(18) 0.0022(17) -0.006(2) C24 0.015(4) 0.016(4) 0.032(4) -0.008(3) 0.003(3) -0.004(3) C25 0.025(5) 0.014(4) 0.048(5) 0.001(4) -0.001(4) 0.004(4) C26 0.044(6) 0.027(5) 0.032(5) 0.010(4) -0.013(4) -0.001(4) O5 0.023(3) 0.044(4) 0.037(4) 0.012(3) 0.010(3) 0.004(3) O6 0.022(4) 0.029(4) 0.021(4) 0.002(2) 0.003(3) 0.014(2) O7 0.031(4) 0.034(3) 0.025(3) 0.004(3) 0.002(2) 0.007(3) F4 0.031(3) 0.054(3) 0.044(4) 0.015(4) 0.021(3) 0.016(3) F5 0.035(3) 0.022(2) 0.043(3) 0.001(2) 0.011(2) -0.001(2) F6 0.042(4) 0.046(3) 0.026(4) -0.015(3) 0.007(3) -0.010(3) #============================================================================== # MOLECULAR GEOMETRY _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 C1 C2 1.404(12) . ? C1 C6 1.419(13) . ? C1 C8 1.473(11) . ? C2 C3 1.351(13) . ? C2 O1 1.387(11) . ? C3 C4 1.397(11) . ? C3 H3 0.9500 . ? C4 C5 1.405(10) . ? C4 C10 1.444(13) . ? C5 C6 1.394(13) . ? C5 H5 0.9500 . ? C6 C7 1.551(16) . ? C7 F2 1.244(15) . ? C7 F1 1.335(11) . ? C7 F3 1.390(9) . ? C8 O2 1.248(11) . ? C8 O3 1.312(9) . ? O8 C26 1.396(12) . ? O8 C23 1.404(15) . ? C9 O3 1.458(12) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 O4 1.319(15) . ? C10 C11 1.362(12) . ? C11 C12 1.400(12) . ? C11 H11 0.9500 . ? C12 C13 1.316(12) . ? C12 H12 0.9500 . ? C13 O4 1.389(12) . ? C13 H13 0.9500 . ? O1 H1 0.8400 . ? C14 C15 1.401(13) . ? C14 C19 1.437(12) . ? C14 C21 1.468(11) . ? C15 O5 1.339(11) . ? C15 C16 1.420(13) . ? C16 C17 1.368(11) . ? C16 H16 0.9500 . ? C17 C18 1.385(10) . ? C17 C23 1.454(13) . ? C18 C19 1.371(12) . ? C18 H18 0.9500 . ? C19 C20 1.437(18) . ? C20 F5 1.352(12) . ? C20 F4 1.362(12) . ? C20 F6 1.400(14) . ? C21 O6 1.225(11) . ? C21 O7 1.313(9) . ? C22 O7 1.437(12) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.345(12) . ? C24 C25 1.423(11) . ? C24 H24 0.9500 . ? C25 C26 1.347(12) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? O5 H5B 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 115.2(8) . . ? C2 C1 C8 117.9(7) . . ? C6 C1 C8 126.9(8) . . ? C3 C2 O1 114.7(8) . . ? C3 C2 C1 124.9(8) . . ? O1 C2 C1 120.3(8) . . ? C2 C3 C4 119.0(8) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 C5 119.4(7) . . ? C3 C4 C10 120.9(8) . . ? C5 C4 C10 119.6(8) . . ? C6 C5 C4 120.1(8) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 121.2(9) . . ? C5 C6 C7 114.5(8) . . ? C1 C6 C7 124.2(8) . . ? F2 C7 F1 110.5(9) . . ? F2 C7 F3 107.8(9) . . ? F1 C7 F3 102.8(7) . . ? F2 C7 C6 115.6(8) . . ? F1 C7 C6 110.7(9) . . ? F3 C7 C6 108.6(8) . . ? O2 C8 O3 120.3(8) . . ? O2 C8 C1 124.6(8) . . ? O3 C8 C1 115.1(7) . . ? C26 O8 C23 103.9(7) . . ? O3 C9 H9A 109.5 . . ? O3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O4 C10 C11 108.8(9) . . ? O4 C10 C4 118.1(9) . . ? C11 C10 C4 133.0(10) . . ? C10 C11 C12 106.9(8) . . ? C10 C11 H11 126.5 . . ? C12 C11 H11 126.5 . . ? C13 C12 C11 107.5(8) . . ? C13 C12 H12 126.2 . . ? C11 C12 H12 126.2 . . ? C12 C13 O4 108.6(8) . . ? C12 C13 H13 125.7 . . ? O4 C13 H13 125.7 . . ? C2 O1 H1 109.5 . . ? C8 O3 C9 117.3(8) . . ? C10 O4 C13 108.1(8) . . ? C15 C14 C19 117.6(7) . . ? C15 C14 C21 115.6(7) . . ? C19 C14 C21 126.8(7) . . ? O5 C15 C14 124.3(8) . . ? O5 C15 C16 115.8(9) . . ? C14 C15 C16 119.9(8) . . ? C17 C16 C15 122.0(8) . . ? C17 C16 H16 119.0 . . ? C15 C16 H16 119.0 . . ? C16 C17 C18 117.4(7) . . ? C16 C17 C23 122.4(8) . . ? C18 C17 C23 120.1(8) . . ? C19 C18 C17 123.6(8) . . ? C19 C18 H18 118.2 . . ? C17 C18 H18 118.2 . . ? C18 C19 C20 117.4(9) . . ? C18 C19 C14 119.4(9) . . ? C20 C19 C14 123.2(8) . . ? F5 C20 F4 103.2(9) . . ? F5 C20 F6 103.7(10) . . ? F4 C20 F6 102.2(9) . . ? F5 C20 C19 115.8(9) . . ? F4 C20 C19 114.4(10) . . ? F6 C20 C19 115.7(9) . . ? O6 C21 O7 121.4(8) . . ? O6 C21 C14 122.9(8) . . ? O7 C21 C14 115.6(7) . . ? O7 C22 H22A 109.5 . . ? O7 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O7 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 O8 111.0(9) . . ? C24 C23 C17 132.9(11) . . ? O8 C23 C17 116.1(8) . . ? C23 C24 C25 107.1(8) . . ? C23 C24 H24 126.5 . . ? C25 C24 H24 126.5 . . ? C26 C25 C24 106.7(7) . . ? C26 C25 H25 126.6 . . ? C24 C25 H25 126.6 . . ? C25 C26 O8 111.3(8) . . ? C25 C26 H26 124.3 . . ? O8 C26 H26 124.3 . . ? C15 O5 H5B 109.5 . . ? C21 O7 C22 116.6(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 C6 C1 C2 C3 5.3(13) . . . . ? C8 C1 C2 C3 -173.0(9) . . . . ? C6 C1 C2 O1 -177.6(8) . . . . ? C8 C1 C2 O1 4.0(12) . . . . ? O1 C2 C3 C4 179.8(7) . . . . ? C1 C2 C3 C4 -3.1(14) . . . . ? C2 C3 C4 C5 -2.0(12) . . . . ? C2 C3 C4 C10 -177.7(8) . . . . ? C3 C4 C5 C6 4.4(12) . . . . ? C10 C4 C5 C6 -179.8(8) . . . . ? C4 C5 C6 C1 -2.0(13) . . . . ? C4 C5 C6 C7 -178.3(7) . . . . ? C2 C1 C6 C5 -2.7(12) . . . . ? C8 C1 C6 C5 175.5(8) . . . . ? C2 C1 C6 C7 173.2(8) . . . . ? C8 C1 C6 C7 -8.6(14) . . . . ? C5 C6 C7 F2 -110.8(9) . . . . ? C1 C6 C7 F2 73.0(11) . . . . ? C5 C6 C7 F1 15.8(11) . . . . ? C1 C6 C7 F1 -160.4(8) . . . . ? C5 C6 C7 F3 128.0(8) . . . . ? C1 C6 C7 F3 -48.2(13) . . . . ? C2 C1 C8 O2 -12.4(12) . . . . ? C6 C1 C8 O2 169.4(8) . . . . ? C2 C1 C8 O3 164.9(7) . . . . ? C6 C1 C8 O3 -13.2(12) . . . . ? C3 C4 C10 O4 -0.6(12) . . . . ? C5 C4 C10 O4 -176.3(8) . . . . ? C3 C4 C10 C11 178.7(9) . . . . ? C5 C4 C10 C11 3.0(14) . . . . ? O4 C10 C11 C12 -1.1(10) . . . . ? C4 C10 C11 C12 179.6(9) . . . . ? C10 C11 C12 C13 0.9(9) . . . . ? C11 C12 C13 O4 -0.4(9) . . . . ? O2 C8 O3 C9 -1.7(12) . . . . ? C1 C8 O3 C9 -179.2(8) . . . . ? C11 C10 O4 C13 0.9(10) . . . . ? C4 C10 O4 C13 -179.7(7) . . . . ? C12 C13 O4 C10 -0.3(10) . . . . ? C19 C14 C15 O5 173.5(9) . . . . ? C21 C14 C15 O5 -9.1(13) . . . . ? C19 C14 C15 C16 -3.8(13) . . . . ? C21 C14 C15 C16 173.6(8) . . . . ? O5 C15 C16 C17 -176.1(8) . . . . ? C14 C15 C16 C17 1.4(14) . . . . ? C15 C16 C17 C18 1.2(12) . . . . ? C15 C16 C17 C23 178.7(8) . . . . ? C16 C17 C18 C19 -1.3(12) . . . . ? C23 C17 C18 C19 -178.9(8) . . . . ? C17 C18 C19 C20 176.0(8) . . . . ? C17 C18 C19 C14 -1.2(13) . . . . ? C15 C14 C19 C18 3.7(13) . . . . ? C21 C14 C19 C18 -173.4(8) . . . . ? C15 C14 C19 C20 -173.3(9) . . . . ? C21 C14 C19 C20 9.5(14) . . . . ? C18 C19 C20 F5 -130.9(9) . . . . ? C14 C19 C20 F5 46.2(14) . . . . ? C18 C19 C20 F4 -11.0(13) . . . . ? C14 C19 C20 F4 166.0(8) . . . . ? C18 C19 C20 F6 107.4(10) . . . . ? C14 C19 C20 F6 -75.5(11) . . . . ? C15 C14 C21 O6 19.8(12) . . . . ? C19 C14 C21 O6 -163.0(8) . . . . ? C15 C14 C21 O7 -161.6(7) . . . . ? C19 C14 C21 O7 15.5(12) . . . . ? C26 O8 C23 C24 -0.7(10) . . . . ? C26 O8 C23 C17 178.4(8) . . . . ? C16 C17 C23 C24 177.6(8) . . . . ? C18 C17 C23 C24 -5.0(15) . . . . ? C16 C17 C23 O8 -1.3(12) . . . . ? C18 C17 C23 O8 176.1(7) . . . . ? O8 C23 C24 C25 0.1(9) . . . . ? C17 C23 C24 C25 -178.9(9) . . . . ? C23 C24 C25 C26 0.6(9) . . . . ? C24 C25 C26 O8 -1.1(10) . . . . ? C23 O8 C26 C25 1.1(10) . . . . ? O6 C21 O7 C22 -0.2(11) . . . . ? C14 C21 O7 C22 -178.7(8) . . . . ? #============================================================================== data_av_y214c1 _database_code_depnum_ccdc_archive 'CCDC 664611' _audit_author_name 'Villinger, A.' _audit_creation_method SHELXL-97 #============================================================================== # CHEMICAL DATA _chemical_name_systematic ; Methyl 4-(thien-2-yl)-6-trifluormethyl-salicylate ; _chemical_name_common 'Methyl 4-(thien-2-yl)-6-trifluormethyl-salicylate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H9 F3 O3 S' _chemical_formula_weight 302.26 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' F F 0.0171 0.0103 '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' #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 2 1' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 13.840(3) _cell_length_b 4.9310(10) _cell_length_c 35.860(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2447.3(9) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2049 _cell_measurement_theta_min 5.978 _cell_measurement_theta_max 44.283 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.90 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.641 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.307 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7696 _exptl_absorpt_correction_T_max 0.9818 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' #============================================================================== # EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7225 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 22.43 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 22.43 _diffrn_measured_fraction_theta_full 0.992 _reflns_number_total 2910 _reflns_number_gt 2510 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex v2.0-2' _computing_cell_refinement 'Bruker Apex v2.0-2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL-97 #============================================================================== # REFINEMENT DATA _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^)+(0.0478P)^2^+2.9174P] 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 SHELXL _refine_ls_extinction_coef 0.0024(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(6) _refine_ls_number_reflns 2910 _refine_ls_number_parameters 361 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1202 _refine_ls_wR_factor_gt 0.1134 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.269 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.063 #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 C1 C 0.3635(5) 1.3898(14) 0.3050(2) 0.0270(18) Uani 1 1 d . . . C2 C 0.3327(5) 1.3362(16) 0.2679(2) 0.0235(18) Uani 1 1 d . . . C3 C 0.3737(5) 1.1382(15) 0.2467(2) 0.0244(17) Uani 1 1 d . . . H3 H 0.3493 1.1050 0.2223 0.029 Uiso 1 1 calc R . . C4 C 0.4499(5) 0.9843(15) 0.25981(19) 0.0225(16) Uani 1 1 d . . . C5 C 0.4880(5) 1.0463(14) 0.2953(2) 0.0238(17) Uani 1 1 d . . . H5 H 0.5430 0.9516 0.3043 0.029 Uiso 1 1 calc R . . C6 C 0.4462(7) 1.2398(14) 0.3164(3) 0.030(3) Uani 1 1 d . . . C7 C 0.4943(7) 1.2981(18) 0.3531(3) 0.037(2) Uani 1 1 d . . . C8 C 0.3063(5) 1.5865(16) 0.3265(2) 0.0284(18) Uani 1 1 d . . . C9 C 0.2648(7) 1.7626(15) 0.3843(3) 0.037(3) Uani 1 1 d . . . H9A H 0.2826 1.9467 0.3766 0.056 Uiso 1 1 calc R . . H9B H 0.2786 1.7390 0.4109 0.056 Uiso 1 1 calc R . . H9C H 0.1957 1.7339 0.3798 0.056 Uiso 1 1 calc R . . C10 C 0.5027(6) 0.7778(14) 0.2369(3) 0.025(2) Uani 1 1 d . . . C11 C 0.5765(4) 0.5978(12) 0.24607(18) 0.0128(8) Uani 1 1 d . . . H11 H 0.6083 0.5903 0.2695 0.015 Uiso 1 1 calc R . . C12 C 0.5970(5) 0.4287(14) 0.2155(2) 0.0315(18) Uani 1 1 d . . . H12 H 0.6454 0.2922 0.2162 0.038 Uiso 1 1 calc R . . C13 C 0.5420(5) 0.4757(14) 0.1846(2) 0.0306(18) Uani 1 1 d . . . H13 H 0.5484 0.3790 0.1618 0.037 Uiso 1 1 calc R . . O1 O 0.2608(3) 1.4767(10) 0.25169(15) 0.0315(12) Uani 1 1 d . . . H1 H 0.2479 1.6140 0.2646 0.047 Uiso 1 1 calc R . . O2 O 0.2484(5) 1.7371(11) 0.3124(2) 0.040(2) Uani 1 1 d . . . O3 O 0.3187(3) 1.5727(11) 0.36342(15) 0.0359(13) Uani 1 1 d . . . F1 F 0.5853(4) 1.1819(10) 0.35516(17) 0.0513(14) Uani 1 1 d . . . F2 F 0.4499(4) 1.2032(10) 0.38478(15) 0.0436(15) Uani 1 1 d . . . F3 F 0.5112(3) 1.5624(8) 0.35969(13) 0.0373(10) Uani 1 1 d . . . S1 S 0.46246(18) 0.7225(4) 0.19160(8) 0.0391(7) Uani 1 1 d . . . C14 C 0.3922(5) -0.3934(14) 0.02992(19) 0.0205(17) Uani 1 1 d . . . C15 C 0.4235(5) -0.3370(16) 0.0666(2) 0.0244(18) Uani 1 1 d . . . C16 C 0.3823(5) -0.1348(15) 0.0880(2) 0.0246(17) Uani 1 1 d . . . H16 H 0.4093 -0.0937 0.1117 0.030 Uiso 1 1 calc R . . C17 C 0.3030(5) 0.0081(14) 0.0758(2) 0.0215(17) Uani 1 1 d . . . C18 C 0.2692(5) -0.0524(14) 0.0398(2) 0.0277(18) Uani 1 1 d . . . H18 H 0.2149 0.0460 0.0309 0.033 Uiso 1 1 calc R . . C19 C 0.3095(6) -0.2455(11) 0.0165(3) 0.019(2) Uani 1 1 d . . . C20 C 0.2572(8) -0.3034(17) -0.0200(3) 0.034(2) Uani 1 1 d . . . C21 C 0.4494(6) -0.5916(16) 0.0085(2) 0.0294(19) Uani 1 1 d . . . C22 C 0.4918(8) -0.784(2) -0.0506(3) 0.052(3) Uani 1 1 d . . . H22A H 0.5565 -0.7074 -0.0541 0.079 Uiso 1 1 calc R . . H22B H 0.4608 -0.8086 -0.0749 0.079 Uiso 1 1 calc R . . H22C H 0.4970 -0.9601 -0.0380 0.079 Uiso 1 1 calc R . . C23 C 0.2621(5) 0.2179(14) 0.0986(3) 0.021(2) Uani 1 1 d . . . C24 C 0.1814(4) 0.3979(12) 0.08886(18) 0.0128(8) Uani 1 1 d . . . H24 H 0.1486 0.4006 0.0656 0.015 Uiso 1 1 calc R . . C25 C 0.1603(5) 0.5662(14) 0.1196(2) 0.0315(19) Uani 1 1 d . . . H25 H 0.1105 0.6988 0.1190 0.038 Uiso 1 1 calc R . . C26 C 0.2158(5) 0.5256(15) 0.1501(2) 0.0341(19) Uani 1 1 d . . . H26 H 0.2094 0.6255 0.1726 0.041 Uiso 1 1 calc R . . O4 O 0.4969(4) -0.4751(11) 0.08297(15) 0.0350(13) Uani 1 1 d . . . H4 H 0.5123 -0.6078 0.0695 0.053 Uiso 1 1 calc R . . O5 O 0.5112(5) -0.7395(9) 0.0225(2) 0.0315(17) Uani 1 1 d . . . O6 O 0.4322(4) -0.5952(11) -0.02721(17) 0.0381(14) Uani 1 1 d . . . F4 F 0.2412(3) -0.5689(8) -0.02364(13) 0.0373(11) Uani 1 1 d . . . F5 F 0.1737(4) -0.1835(10) -0.02105(15) 0.0442(13) Uani 1 1 d . . . F6 F 0.3075(4) -0.2191(9) -0.04870(16) 0.0425(16) Uani 1 1 d . . . S2 S 0.29815(17) 0.2757(4) 0.14346(7) 0.0330(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.029(4) 0.022(4) 0.030(5) 0.003(4) -0.003(4) -0.003(3) C2 0.018(4) 0.022(4) 0.031(5) 0.016(4) 0.003(4) 0.002(3) C3 0.029(4) 0.027(5) 0.018(4) -0.010(4) -0.004(4) -0.001(3) C4 0.028(4) 0.025(4) 0.014(4) 0.000(3) -0.003(3) -0.006(3) C5 0.016(4) 0.019(4) 0.036(5) 0.004(4) -0.005(3) -0.001(3) C6 0.039(5) 0.030(6) 0.021(7) 0.004(4) -0.011(4) 0.002(3) C7 0.041(5) 0.042(5) 0.029(6) 0.011(5) -0.011(5) 0.022(4) C8 0.018(4) 0.030(4) 0.036(6) -0.002(4) 0.007(4) -0.002(3) C9 0.027(5) 0.047(6) 0.037(7) -0.014(4) -0.007(4) 0.006(4) C10 0.044(5) 0.015(4) 0.016(5) -0.004(3) 0.007(4) -0.022(3) C11 0.0157(19) 0.0103(19) 0.0122(19) -0.0011(16) 0.0026(15) -0.0053(15) C12 0.037(4) 0.017(4) 0.041(5) 0.006(4) 0.003(4) 0.010(3) C13 0.038(4) 0.019(4) 0.035(4) -0.009(4) 0.008(4) -0.008(3) O1 0.032(3) 0.029(3) 0.033(3) -0.002(2) -0.009(2) 0.010(2) O2 0.031(3) 0.054(5) 0.036(5) -0.003(3) -0.003(4) 0.020(3) O3 0.040(3) 0.047(3) 0.020(3) -0.002(3) -0.001(2) 0.008(3) F1 0.047(3) 0.058(3) 0.049(4) -0.021(3) -0.019(3) 0.028(3) F2 0.060(3) 0.048(3) 0.023(4) 0.012(3) 0.002(3) 0.002(2) F3 0.046(3) 0.029(3) 0.037(2) -0.005(2) -0.013(2) -0.004(2) S1 0.0468(15) 0.0341(14) 0.0363(19) -0.0044(11) -0.0071(12) 0.0117(9) C14 0.020(4) 0.022(4) 0.019(4) -0.001(3) 0.008(3) -0.004(3) C15 0.030(4) 0.013(4) 0.030(5) -0.006(4) -0.001(4) -0.001(4) C16 0.018(4) 0.025(5) 0.031(5) 0.002(4) 0.005(3) -0.006(3) C17 0.019(4) 0.012(4) 0.033(5) -0.002(3) 0.003(3) -0.008(3) C18 0.038(4) 0.018(4) 0.027(5) -0.001(4) -0.002(3) 0.000(3) C19 0.016(4) 0.017(5) 0.024(6) 0.000(3) 0.003(4) -0.001(3) C20 0.057(7) 0.022(4) 0.024(6) -0.007(4) 0.003(5) -0.006(4) C21 0.044(5) 0.026(4) 0.019(5) -0.003(4) 0.001(4) -0.009(4) C22 0.062(7) 0.061(7) 0.034(7) -0.016(5) 0.027(5) 0.020(5) C23 0.009(4) 0.024(5) 0.030(5) 0.007(3) -0.001(3) 0.000(3) C24 0.0157(19) 0.0103(19) 0.0122(19) -0.0011(16) 0.0026(15) -0.0053(15) C25 0.020(4) 0.020(4) 0.055(5) 0.004(4) 0.003(4) -0.004(3) C26 0.050(5) 0.029(4) 0.023(4) 0.004(4) 0.006(4) 0.001(4) O4 0.035(3) 0.037(3) 0.033(3) -0.012(3) -0.009(3) 0.011(3) O5 0.042(4) 0.022(4) 0.030(4) -0.004(2) -0.001(3) 0.009(3) O6 0.043(3) 0.042(3) 0.029(4) -0.008(3) 0.003(3) 0.021(3) F4 0.047(3) 0.032(3) 0.033(3) -0.003(2) -0.005(2) -0.004(2) F5 0.051(3) 0.049(3) 0.033(3) -0.011(3) -0.023(2) 0.007(3) F6 0.068(4) 0.037(3) 0.023(4) 0.004(2) -0.011(3) -0.004(2) S2 0.0416(14) 0.0294(13) 0.0282(16) -0.0034(10) -0.0023(12) 0.0003(9) #============================================================================== # MOLECULAR GEOMETRY _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 C1 C2 1.422(10) . ? C1 C6 1.424(11) . ? C1 C8 1.470(10) . ? C2 O1 1.345(8) . ? C2 C3 1.361(11) . ? C3 C4 1.383(10) . ? C3 H3 0.9500 . ? C4 C5 1.411(9) . ? C4 C10 1.499(11) . ? C5 C6 1.348(12) . ? C5 H5 0.9500 . ? C6 C7 1.505(16) . ? C7 F3 1.345(10) . ? C7 F2 1.372(12) . ? C7 F1 1.386(11) . ? C8 O2 1.205(9) . ? C8 O3 1.337(9) . ? C9 O3 1.411(10) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.392(10) . ? C10 S1 1.739(10) . ? C11 C12 1.408(9) . ? C11 H11 0.9500 . ? C12 C13 1.364(10) . ? C12 H12 0.9500 . ? C13 S1 1.660(8) . ? C13 H13 0.9500 . ? O1 H1 0.8400 . ? C14 C15 1.411(10) . ? C14 C19 1.439(11) . ? C14 C21 1.474(10) . ? C15 O4 1.357(9) . ? C15 C16 1.382(11) . ? C16 C17 1.375(10) . ? C16 H16 0.9500 . ? C17 C18 1.405(10) . ? C17 C23 1.435(11) . ? C18 C19 1.385(11) . ? C18 H18 0.9500 . ? C19 C20 1.523(15) . ? C20 F5 1.299(11) . ? C20 F6 1.311(12) . ? C20 F4 1.334(9) . ? C21 O5 1.231(10) . ? C21 O6 1.302(9) . ? C22 O6 1.500(11) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.469(10) . ? C23 S2 1.708(10) . ? C24 C25 1.411(10) . ? C24 H24 0.9500 . ? C25 C26 1.350(10) . ? C25 H25 0.9500 . ? C26 S2 1.695(8) . ? C26 H26 0.9500 . ? O4 H4 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 114.4(7) . . ? C2 C1 C8 116.9(7) . . ? C6 C1 C8 128.7(8) . . ? O1 C2 C3 115.9(7) . . ? O1 C2 C1 122.0(7) . . ? C3 C2 C1 122.2(7) . . ? C2 C3 C4 121.3(7) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C3 C4 C5 118.3(6) . . ? C3 C4 C10 123.9(6) . . ? C5 C4 C10 117.3(7) . . ? C6 C5 C4 119.9(7) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 123.5(9) . . ? C5 C6 C7 115.9(8) . . ? C1 C6 C7 120.5(8) . . ? F3 C7 F2 105.3(8) . . ? F3 C7 F1 103.5(7) . . ? F2 C7 F1 102.9(7) . . ? F3 C7 C6 114.5(7) . . ? F2 C7 C6 117.5(8) . . ? F1 C7 C6 111.6(8) . . ? O2 C8 O3 122.2(7) . . ? O2 C8 C1 123.0(8) . . ? O3 C8 C1 114.7(7) . . ? O3 C9 H9A 109.5 . . ? O3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C4 131.4(8) . . ? C11 C10 S1 110.8(6) . . ? C4 C10 S1 117.5(6) . . ? C10 C11 C12 110.0(6) . . ? C10 C11 H11 125.0 . . ? C12 C11 H11 125.0 . . ? C13 C12 C11 114.8(6) . . ? C13 C12 H12 122.6 . . ? C11 C12 H12 122.6 . . ? C12 C13 S1 111.8(6) . . ? C12 C13 H13 124.1 . . ? S1 C13 H13 124.1 . . ? C2 O1 H1 109.5 . . ? C8 O3 C9 115.0(7) . . ? C13 S1 C10 92.5(4) . . ? C15 C14 C19 117.1(7) . . ? C15 C14 C21 116.8(7) . . ? C19 C14 C21 126.0(7) . . ? O4 C15 C16 115.5(7) . . ? O4 C15 C14 122.3(6) . . ? C16 C15 C14 122.2(7) . . ? C17 C16 C15 121.5(7) . . ? C17 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C16 C17 C18 116.7(7) . . ? C16 C17 C23 120.3(7) . . ? C18 C17 C23 123.0(7) . . ? C19 C18 C17 124.5(8) . . ? C19 C18 H18 117.8 . . ? C17 C18 H18 117.8 . . ? C18 C19 C14 117.8(9) . . ? C18 C19 C20 117.2(7) . . ? C14 C19 C20 124.8(7) . . ? F5 C20 F6 107.8(8) . . ? F5 C20 F4 107.2(7) . . ? F6 C20 F4 108.8(7) . . ? F5 C20 C19 111.3(7) . . ? F6 C20 C19 111.3(8) . . ? F4 C20 C19 110.3(8) . . ? O5 C21 O6 121.3(7) . . ? O5 C21 C14 123.6(7) . . ? O6 C21 C14 115.1(7) . . ? O6 C22 H22A 109.5 . . ? O6 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O6 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C17 C23 C24 126.9(8) . . ? C17 C23 S2 122.7(6) . . ? C24 C23 S2 110.2(6) . . ? C25 C24 C23 109.1(6) . . ? C25 C24 H24 125.5 . . ? C23 C24 H24 125.5 . . ? C26 C25 C24 115.3(7) . . ? C26 C25 H25 122.4 . . ? C24 C25 H25 122.4 . . ? C25 C26 S2 112.2(6) . . ? C25 C26 H26 123.9 . . ? S2 C26 H26 123.9 . . ? C15 O4 H4 109.5 . . ? C21 O6 C22 117.2(7) . . ? C26 S2 C23 93.2(4) . . ? 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 C6 C1 C2 O1 -174.4(7) . . . . ? C8 C1 C2 O1 6.4(10) . . . . ? C6 C1 C2 C3 6.2(11) . . . . ? C8 C1 C2 C3 -173.1(7) . . . . ? O1 C2 C3 C4 178.3(6) . . . . ? C1 C2 C3 C4 -2.2(12) . . . . ? C2 C3 C4 C5 -3.1(11) . . . . ? C2 C3 C4 C10 -175.4(7) . . . . ? C3 C4 C5 C6 4.1(10) . . . . ? C10 C4 C5 C6 176.8(7) . . . . ? C4 C5 C6 C1 0.3(12) . . . . ? C4 C5 C6 C7 -177.8(7) . . . . ? C2 C1 C6 C5 -5.3(12) . . . . ? C8 C1 C6 C5 173.9(8) . . . . ? C2 C1 C6 C7 172.8(8) . . . . ? C8 C1 C6 C7 -8.1(13) . . . . ? C5 C6 C7 F3 130.2(8) . . . . ? C1 C6 C7 F3 -48.0(12) . . . . ? C5 C6 C7 F2 -105.5(10) . . . . ? C1 C6 C7 F2 76.4(10) . . . . ? C5 C6 C7 F1 13.0(12) . . . . ? C1 C6 C7 F1 -165.2(8) . . . . ? C2 C1 C8 O2 -14.4(10) . . . . ? C6 C1 C8 O2 166.4(8) . . . . ? C2 C1 C8 O3 161.1(6) . . . . ? C6 C1 C8 O3 -18.0(11) . . . . ? C3 C4 C10 C11 -176.2(7) . . . . ? C5 C4 C10 C11 11.5(11) . . . . ? C3 C4 C10 S1 -2.1(9) . . . . ? C5 C4 C10 S1 -174.4(5) . . . . ? C4 C10 C11 C12 175.3(7) . . . . ? S1 C10 C11 C12 1.0(7) . . . . ? C10 C11 C12 C13 -0.1(8) . . . . ? C11 C12 C13 S1 -0.9(8) . . . . ? O2 C8 O3 C9 -5.0(10) . . . . ? C1 C8 O3 C9 179.4(6) . . . . ? C12 C13 S1 C10 1.2(6) . . . . ? C11 C10 S1 C13 -1.3(6) . . . . ? C4 C10 S1 C13 -176.5(5) . . . . ? C19 C14 C15 O4 176.0(7) . . . . ? C21 C14 C15 O4 -6.1(10) . . . . ? C19 C14 C15 C16 -4.9(10) . . . . ? C21 C14 C15 C16 173.0(7) . . . . ? O4 C15 C16 C17 -175.4(6) . . . . ? C14 C15 C16 C17 5.4(12) . . . . ? C15 C16 C17 C18 -3.1(10) . . . . ? C15 C16 C17 C23 -179.7(7) . . . . ? C16 C17 C18 C19 0.7(11) . . . . ? C23 C17 C18 C19 177.2(7) . . . . ? C17 C18 C19 C14 -0.4(11) . . . . ? C17 C18 C19 C20 174.1(7) . . . . ? C15 C14 C19 C18 2.4(10) . . . . ? C21 C14 C19 C18 -175.3(7) . . . . ? C15 C14 C19 C20 -171.6(8) . . . . ? C21 C14 C19 C20 10.7(12) . . . . ? C18 C19 C20 F5 -8.7(11) . . . . ? C14 C19 C20 F5 165.4(7) . . . . ? C18 C19 C20 F6 111.6(9) . . . . ? C14 C19 C20 F6 -74.4(10) . . . . ? C18 C19 C20 F4 -127.5(8) . . . . ? C14 C19 C20 F4 46.5(11) . . . . ? C15 C14 C21 O5 12.4(11) . . . . ? C19 C14 C21 O5 -169.9(7) . . . . ? C15 C14 C21 O6 -165.6(6) . . . . ? C19 C14 C21 O6 12.2(11) . . . . ? C16 C17 C23 C24 176.4(7) . . . . ? C18 C17 C23 C24 0.0(11) . . . . ? C16 C17 C23 S2 -8.1(10) . . . . ? C18 C17 C23 S2 175.5(6) . . . . ? C17 C23 C24 C25 177.1(7) . . . . ? S2 C23 C24 C25 1.1(7) . . . . ? C23 C24 C25 C26 -0.5(8) . . . . ? C24 C25 C26 S2 -0.3(8) . . . . ? O5 C21 O6 C22 -0.8(11) . . . . ? C14 C21 O6 C22 177.2(7) . . . . ? C25 C26 S2 C23 0.9(6) . . . . ? C17 C23 S2 C26 -177.3(6) . . . . ? C24 C23 S2 C26 -1.1(5) . . . . ? #============================================================================== data_FO3241 _database_code_depnum_ccdc_archive 'CCDC 675254' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 O3 S' _chemical_formula_weight 262.31 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 P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0866(5) _cell_length_b 9.2066(7) _cell_length_c 10.2121(9) _cell_angle_alpha 95.843(4) _cell_angle_beta 105.477(5) _cell_angle_gamma 98.661(5) _cell_volume 627.70(9) _cell_formula_units_Z 2 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 4319 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 27.42 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.255 _exptl_absorpt_correction_type NONE _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 KappaCCD _diffrn_measurement_method 'phi- + omega-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4319 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0914 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.42 _reflns_number_total 2743 _reflns_number_gt 1645 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement DENZO _computing_data_reduction DENZO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXL-97 _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^)+(0.1008P)^2^+1.4708P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2743 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1367 _refine_ls_R_factor_gt 0.0757 _refine_ls_wR_factor_ref 0.2341 _refine_ls_wR_factor_gt 0.1982 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.003 _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 S S 0.7860(2) 0.35102(15) 0.04290(14) 0.0404(4) Uani 1 1 d . . . O1 O 0.7992(5) 0.3946(4) 0.5998(4) 0.0301(8) Uani 1 1 d . . . O2 O 0.5520(5) 0.4601(3) 0.3759(3) 0.0337(8) Uani 1 1 d . . . O3 O 0.4672(4) 0.2722(3) 0.2018(3) 0.0265(7) Uani 1 1 d . . . C1 C 0.7142(7) 0.2476(5) -0.1119(5) 0.0332(11) Uani 1 1 d . . . H1A H 0.6875 0.2882 -0.1954 0.040 Uiso 1 1 calc R . . C2 C 0.6977(7) 0.0994(5) -0.1068(5) 0.0349(11) Uani 1 1 d . . . H2A H 0.6550 0.0279 -0.1876 0.042 Uiso 1 1 calc R . . C3 C 0.7502(5) 0.0559(4) 0.0321(4) 0.0180(8) Uiso 1 1 d . . . H3A H 0.7546 -0.0410 0.0556 0.022 Uiso 1 1 calc R . . C4 C 0.7946(6) 0.1993(5) 0.1269(4) 0.0217(9) Uani 1 1 d . . . C5 C 0.8645(6) 0.2158(4) 0.2791(4) 0.0201(9) Uani 1 1 d . . . C6 C 0.7788(6) 0.2949(4) 0.3673(4) 0.0203(9) Uani 1 1 d . . . C7 C 0.8705(6) 0.3167(4) 0.5094(4) 0.0211(9) Uani 1 1 d . . . C8 C 1.0389(6) 0.2569(4) 0.5668(4) 0.0234(9) Uani 1 1 d . . . C9 C 1.1193(6) 0.1762(5) 0.4779(5) 0.0241(9) Uani 1 1 d . . . C10 C 1.0317(6) 0.1580(5) 0.3379(4) 0.0236(9) Uani 1 1 d . . . H10A H 1.0884 0.1034 0.2791 0.028 Uiso 1 1 calc R . . C12 C 0.2989(6) 0.3350(5) 0.1358(5) 0.0329(11) Uani 1 1 d . . . H12A H 0.2023 0.2589 0.0660 0.049 Uiso 1 1 calc R . . H12B H 0.3436 0.4182 0.0919 0.049 Uiso 1 1 calc R . . H12C H 0.2360 0.3706 0.2044 0.049 Uiso 1 1 calc R . . C11 C 0.5929(6) 0.3522(5) 0.3162(5) 0.0231(9) Uani 1 1 d . . . C13 C 1.1291(7) 0.2810(5) 0.7201(5) 0.0333(11) Uani 1 1 d . . . H13A H 1.2747 0.3024 0.7418 0.050 Uiso 1 1 calc R . . H13B H 1.0878 0.1912 0.7571 0.050 Uiso 1 1 calc R . . H13C H 1.0835 0.3649 0.7613 0.050 Uiso 1 1 calc R . . C14 C 1.3057(6) 0.1127(5) 0.5326(5) 0.0338(11) Uani 1 1 d . . . H14A H 1.3308 0.0512 0.4571 0.051 Uiso 1 1 calc R . . H14B H 1.2871 0.0518 0.6030 0.051 Uiso 1 1 calc R . . H14C H 1.4196 0.1942 0.5728 0.051 Uiso 1 1 calc R . . H1O1 H 0.743(8) 0.435(6) 0.575(6) 0.027(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S 0.0446(8) 0.0428(8) 0.0345(8) 0.0099(6) 0.0092(6) 0.0114(6) O1 0.0361(19) 0.037(2) 0.0221(19) 0.0048(15) 0.0096(15) 0.0194(16) O2 0.0325(17) 0.0370(19) 0.033(2) -0.0028(15) 0.0079(14) 0.0200(14) O3 0.0209(14) 0.0270(16) 0.0299(18) 0.0019(13) 0.0023(13) 0.0096(12) C1 0.032(2) 0.047(3) 0.021(3) 0.008(2) 0.0071(19) 0.010(2) C2 0.041(3) 0.041(3) 0.022(3) -0.006(2) 0.008(2) 0.010(2) C4 0.0186(19) 0.029(2) 0.019(2) 0.0033(17) 0.0060(16) 0.0077(16) C5 0.0211(19) 0.020(2) 0.020(2) 0.0046(16) 0.0062(16) 0.0034(15) C6 0.0195(19) 0.021(2) 0.025(2) 0.0057(17) 0.0096(17) 0.0080(15) C7 0.026(2) 0.019(2) 0.019(2) 0.0019(16) 0.0091(17) 0.0050(16) C8 0.022(2) 0.023(2) 0.023(2) 0.0045(17) 0.0040(17) 0.0029(16) C9 0.022(2) 0.025(2) 0.026(2) 0.0100(18) 0.0055(18) 0.0080(17) C10 0.023(2) 0.029(2) 0.026(2) 0.0070(18) 0.0120(18) 0.0141(17) C12 0.024(2) 0.039(3) 0.038(3) 0.011(2) 0.006(2) 0.0163(19) C11 0.028(2) 0.024(2) 0.022(2) 0.0088(18) 0.0106(18) 0.0087(17) C13 0.035(2) 0.040(3) 0.025(3) 0.008(2) 0.006(2) 0.012(2) C14 0.026(2) 0.043(3) 0.034(3) 0.010(2) 0.004(2) 0.015(2) _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 S C1 1.668(5) . ? S C4 1.713(4) . ? O1 C7 1.358(5) . ? O1 H1O1 0.61(5) . ? O2 C11 1.225(5) . ? O3 C11 1.331(5) . ? O3 C12 1.438(5) . ? C1 C2 1.359(7) . ? C1 H1A 0.9500 . ? C2 C3 1.480(6) . ? C2 H2A 0.9500 . ? C3 C4 1.493(6) . ? C3 H3A 0.9500 . ? C4 C5 1.484(6) . ? C5 C10 1.386(5) . ? C5 C6 1.416(5) . ? C6 C7 1.402(6) . ? C6 C11 1.478(5) . ? C7 C8 1.400(5) . ? C8 C9 1.402(6) . ? C8 C13 1.504(6) . ? C9 C10 1.381(6) . ? C9 C14 1.517(5) . ? C10 H10A 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? 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 C1 S C4 93.1(2) . . ? C7 O1 H1O1 116(6) . . ? C11 O3 C12 116.5(3) . . ? C2 C1 S 113.3(4) . . ? C2 C1 H1A 123.3 . . ? S C1 H1A 123.3 . . ? C1 C2 C3 116.1(4) . . ? C1 C2 H2A 122.0 . . ? C3 C2 H2A 122.0 . . ? C2 C3 C4 104.2(3) . . ? C2 C3 H3A 127.9 . . ? C4 C3 H3A 127.9 . . ? C5 C4 C3 125.1(3) . . ? C5 C4 S 121.4(3) . . ? C3 C4 S 113.1(3) . . ? C10 C5 C6 118.3(4) . . ? C10 C5 C4 117.7(4) . . ? C6 C5 C4 123.9(3) . . ? C7 C6 C5 118.8(3) . . ? C7 C6 C11 118.4(4) . . ? C5 C6 C11 122.7(4) . . ? O1 C7 C8 116.0(4) . . ? O1 C7 C6 122.0(4) . . ? C8 C7 C6 122.0(4) . . ? C7 C8 C9 118.3(4) . . ? C7 C8 C13 119.8(4) . . ? C9 C8 C13 121.9(4) . . ? C10 C9 C8 119.6(4) . . ? C10 C9 C14 119.2(4) . . ? C8 C9 C14 121.2(4) . . ? C9 C10 C5 122.9(4) . . ? C9 C10 H10A 118.5 . . ? C5 C10 H10A 118.5 . . ? O3 C12 H12A 109.5 . . ? O3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O2 C11 O3 122.1(4) . . ? O2 C11 C6 123.6(4) . . ? O3 C11 C6 114.2(3) . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 1.090 _refine_diff_density_min -0.609 _refine_diff_density_rms 0.098