# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2002 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name D.R.Boyd N.D.Sharma N.Gunaratne S.A.Haughey M.A.Kennedy ; J.F.Malone ; C.C.R.Allen H.Dalton _publ_contact_author_name 'Professor D.R. Boyd' _publ_contact_author_address ; School of Chemistry Queen's University Belfast BT9 5AG UK ; _publ_contact_author_email dr.boyd@qub.ac.uk _publ_section_title ; Dioxygenase-catalysed oxidation of 2-substituted thiophenes: cycloadduct formation ; data_7D _database_code_CSD 192255 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (+/-)-2,4-dichloro-cis-3a,4,7,7a-tetrahydro-cis-4,7-epithio- 1-benzothiophene-trans-1-syn-8-dioxide ; _chemical_name_common ? _chemical_melting_point 129-131 _chemical_formula_moiety 'C8 H6 Cl2 O2 S2' _chemical_formula_sum 'C8 H6 Cl2 O2 S2' _chemical_formula_weight 269.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.283(3) _cell_length_b 12.655(4) _cell_length_c 9.554(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.09(2) _cell_angle_gamma 90.00 _cell_volume 1001.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour ? _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.43 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.785 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 9.487 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.0657 _exptl_absorpt_correction_T_max 0.1058 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P3 diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1409 _diffrn_reflns_av_R_equivalents 0.0671 _diffrn_reflns_av_sigmaI/netI 0.0711 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.80 _diffrn_reflns_theta_max 54.98 _reflns_number_total 724 _reflns_number_gt 600 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3/V2000' _computing_cell_refinement 'Siemens P3/V2000' _computing_data_reduction 'Siemens P3/V2000' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1296P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment geom _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0093(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 724 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0683 _refine_ls_wR_factor_ref 0.1817 _refine_ls_wR_factor_gt 0.1779 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl4 Cl 0.4338(3) 0.00964(19) 0.3280(3) 0.0394(13) Uani 1 1 d . . . Cl7 Cl -0.0251(4) 0.35246(18) 0.4751(3) 0.0424(13) Uani 1 1 d . . . S3 S 0.1435(3) 0.02389(18) 0.1445(3) 0.0283(12) Uani 1 1 d . . . S10 S -0.2428(4) 0.24054(19) 0.2656(3) 0.0354(13) Uani 1 1 d . . . O3 O 0.0656(9) -0.0741(5) 0.1991(8) 0.040(3) Uani 1 1 d . . . O10 O -0.2221(12) 0.3154(5) 0.1477(9) 0.053(4) Uani 1 1 d . . . C1 C -0.1627(14) 0.1060(7) 0.2203(12) 0.025(4) Uani 1 1 d . . . H1 H -0.2309 0.0637 0.1577 0.030 Uiso 1 1 calc R . . C2 C 0.0046(13) 0.1375(6) 0.1610(11) 0.025(4) Uani 1 1 d . . . H2 H -0.0101 0.1700 0.0688 0.030 Uiso 1 1 calc R . . C4 C 0.2706(12) 0.0806(7) 0.2771(11) 0.030(4) Uani 1 1 d . . . C5 C 0.2300(14) 0.1775(7) 0.3188(12) 0.032(4) Uani 1 1 d . . . H5 H 0.2939 0.2162 0.3803 0.039 Uiso 1 1 calc R . . C6 C 0.0779(12) 0.2195(7) 0.2618(12) 0.027(4) Uani 1 1 d . . . H6 H 0.0984 0.2858 0.2119 0.032 Uiso 1 1 calc R . . C7 C -0.0553(13) 0.2364(7) 0.3733(11) 0.028(4) Uani 1 1 d . . . C8 C -0.0915(12) 0.1379(7) 0.4508(11) 0.029(4) Uani 1 1 d . . . H8 H -0.0759 0.1290 0.5465 0.035 Uiso 1 1 calc R . . C9 C -0.1478(13) 0.0655(7) 0.3676(12) 0.026(4) Uani 1 1 d . . . H9 H -0.1753 -0.0026 0.3957 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl4 0.024(2) 0.0494(17) 0.044(2) -0.0072(15) -0.010(2) 0.0072(13) Cl7 0.059(2) 0.0371(15) 0.0314(19) -0.0171(12) 0.007(2) 0.0044(14) S3 0.032(2) 0.0314(15) 0.0219(17) -0.0070(12) 0.000(2) 0.0043(12) S10 0.035(2) 0.0373(16) 0.034(2) 0.0019(14) 0.000(2) 0.0126(14) O3 0.042(6) 0.029(4) 0.050(6) 0.002(4) 0.004(6) 0.000(4) O10 0.073(8) 0.043(4) 0.042(6) 0.010(4) 0.000(8) 0.021(5) C1 0.020(8) 0.029(5) 0.025(8) -0.005(6) -0.018(10) 0.001(6) C2 0.033(8) 0.022(5) 0.020(7) -0.002(5) -0.001(9) 0.005(5) C4 0.025(7) 0.041(6) 0.026(7) -0.013(6) 0.012(8) -0.012(5) C5 0.039(8) 0.030(5) 0.028(8) -0.009(5) 0.016(9) -0.008(5) C6 0.026(7) 0.026(5) 0.029(8) -0.004(5) 0.009(9) -0.002(5) C7 0.036(7) 0.025(5) 0.023(7) -0.004(5) 0.012(8) 0.002(5) C8 0.027(7) 0.041(6) 0.020(7) 0.005(6) 0.013(8) 0.009(6) C9 0.025(8) 0.021(5) 0.033(8) 0.004(5) 0.006(9) 0.003(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl4 C4 1.694(12) . ? Cl7 C7 1.779(10) . ? S3 O3 1.493(6) . ? S3 C4 1.796(12) . ? S3 C2 1.848(9) . ? S10 O10 1.482(8) . ? S10 C7 1.863(14) . ? S10 C1 1.879(9) . ? C1 C9 1.503(18) . ? C1 C2 1.550(13) . ? C2 C6 1.541(16) . ? C4 C5 1.332(13) . ? C5 C6 1.471(18) . ? C6 C7 1.549(10) . ? C7 C8 1.480(12) . ? C8 C9 1.299(15) . ? 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 O3 S3 C4 109.8(5) . . ? O3 S3 C2 110.3(4) . . ? C4 S3 C2 89.6(5) . . ? O10 S10 C7 109.9(5) . . ? O10 S10 C1 111.3(4) . . ? C7 S10 C1 78.9(5) . . ? C9 C1 C2 111.0(11) . . ? C9 C1 S10 97.0(6) . . ? C2 C1 S10 99.6(6) . . ? C6 C2 C1 107.2(6) . . ? C6 C2 S3 109.4(8) . . ? C1 C2 S3 112.8(6) . . ? C5 C4 Cl4 127.2(11) . . ? C5 C4 S3 115.5(10) . . ? Cl4 C4 S3 117.2(5) . . ? C4 C5 C6 116.1(12) . . ? C5 C6 C2 108.9(7) . . ? C5 C6 C7 113.9(10) . . ? C2 C6 C7 104.0(8) . . ? C8 C7 C6 111.9(6) . . ? C8 C7 Cl7 116.8(7) . . ? C6 C7 Cl7 112.9(7) . . ? C8 C7 S10 97.5(8) . . ? C6 C7 S10 102.6(8) . . ? Cl7 C7 S10 113.3(5) . . ? C9 C8 C7 111.2(9) . . ? C8 C9 C1 111.2(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 O10 S10 C1 C9 161.3(8) . . . . ? C7 S10 C1 C9 54.1(8) . . . . ? O10 S10 C1 C2 48.6(10) . . . . ? C7 S10 C1 C2 -58.6(7) . . . . ? C9 C1 C2 C6 -56.4(10) . . . . ? S10 C1 C2 C6 45.0(9) . . . . ? C9 C1 C2 S3 64.2(10) . . . . ? S10 C1 C2 S3 165.6(7) . . . . ? O3 S3 C2 C6 116.6(6) . . . . ? C4 S3 C2 C6 5.6(6) . . . . ? O3 S3 C2 C1 -2.7(10) . . . . ? C4 S3 C2 C1 -113.7(8) . . . . ? O3 S3 C4 C5 -118.5(6) . . . . ? C2 S3 C4 C5 -7.0(6) . . . . ? O3 S3 C4 Cl4 65.2(5) . . . . ? C2 S3 C4 Cl4 176.7(5) . . . . ? Cl4 C4 C5 C6 -177.8(6) . . . . ? S3 C4 C5 C6 6.3(9) . . . . ? C4 C5 C6 C2 -1.6(10) . . . . ? C4 C5 C6 C7 114.0(9) . . . . ? C1 C2 C6 C5 119.2(8) . . . . ? S3 C2 C6 C5 -3.5(8) . . . . ? C1 C2 C6 C7 -2.6(10) . . . . ? S3 C2 C6 C7 -125.3(7) . . . . ? C5 C6 C7 C8 -56.6(13) . . . . ? C2 C6 C7 C8 61.8(13) . . . . ? C5 C6 C7 Cl7 77.6(9) . . . . ? C2 C6 C7 Cl7 -164.0(7) . . . . ? C5 C6 C7 S10 -160.1(7) . . . . ? C2 C6 C7 S10 -41.7(8) . . . . ? O10 S10 C7 C8 -164.3(5) . . . . ? C1 S10 C7 C8 -55.5(5) . . . . ? O10 S10 C7 C6 -49.8(6) . . . . ? C1 S10 C7 C6 59.0(5) . . . . ? O10 S10 C7 Cl7 72.2(5) . . . . ? C1 S10 C7 Cl7 -178.9(5) . . . . ? C6 C7 C8 C9 -62.7(13) . . . . ? Cl7 C7 C8 C9 165.0(8) . . . . ? S10 C7 C8 C9 44.1(8) . . . . ? C7 C8 C9 C1 -1.7(12) . . . . ? C2 C1 C9 C8 62.1(10) . . . . ? S10 C1 C9 C8 -41.1(10) . . . . ? _diffrn_measured_fraction_theta_max 0.578 _diffrn_reflns_theta_full 54.98 _diffrn_measured_fraction_theta_full 0.578 _refine_diff_density_max 0.553 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.129 #===END data_17 _database_code_CSD 192256 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (+/-)-6-acetyl-1-methyl-7lambda4-thiabicyclo[2.2.1]hepta-2-en-7-one ; _chemical_name_common ? _chemical_melting_point 88-90 _chemical_formula_moiety 'C9 H12 O2 S' _chemical_formula_sum 'C9 H12 O2 S' _chemical_formula_weight 184.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.1658(9) _cell_length_b 6.6249(5) _cell_length_c 13.2296(10) _cell_angle_alpha 90.00 _cell_angle_beta 111.5260(12) _cell_angle_gamma 90.00 _cell_volume 910.37(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.311 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.9263 _exptl_absorpt_correction_T_max 0.9404 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker SMART CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9434 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 28.32 _reflns_number_total 2063 _reflns_number_gt 1794 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1806P)^2^+4.6515P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment geom _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2063 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1014 _refine_ls_R_factor_gt 0.0912 _refine_ls_wR_factor_ref 0.2759 _refine_ls_wR_factor_gt 0.2658 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _refine_ls_shift/su_max 0.351 _refine_ls_shift/su_mean 0.009 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.69587(9) 0.82804(15) 0.09655(8) 0.0258(4) Uani 1 1 d . . . O1 O 0.5648(3) 0.7681(5) 0.0915(3) 0.0351(8) Uani 1 1 d . . . O2 O 0.5932(5) 0.3823(9) -0.2459(4) 0.0648(13) Uani 1 1 d . . . C1 C 0.7687(4) 0.6200(6) 0.0431(3) 0.0216(8) Uani 1 1 d . . . C2 C 0.6601(3) 0.5792(6) -0.0675(3) 0.0201(8) Uani 1 1 d . . . H2 H 0.5887 0.5084 -0.0533 0.024 Uiso 1 1 calc R . . C3 C 0.6090(4) 0.7893(7) -0.1177(3) 0.0273(9) Uani 1 1 d . . . H3A H 0.6228 0.8088 -0.1868 0.033 Uiso 1 1 calc R . . H3B H 0.5159 0.8025 -0.1318 0.033 Uiso 1 1 calc R . . C4 C 0.6876(4) 0.9441(6) -0.0318(4) 0.0263(9) Uani 1 1 d . . . H4 H 0.6529 1.0849 -0.0436 0.032 Uiso 1 1 calc R . . C5 C 0.8287(4) 0.9263(7) -0.0117(4) 0.0291(9) Uani 1 1 d . . . H5 H 0.8791 1.0297 -0.0261 0.035 Uiso 1 1 calc R . . C6 C 0.8730(4) 0.7463(7) 0.0288(3) 0.0262(9) Uani 1 1 d . . . H6 H 0.9594 0.7030 0.0465 0.031 Uiso 1 1 calc R . . C7 C 0.8085(5) 0.4417(7) 0.1198(4) 0.0325(10) Uani 1 1 d . . . H7A H 0.8534 0.3425 0.0917 0.049 Uiso 1 1 calc R . . H7B H 0.7318 0.3794 0.1259 0.049 Uiso 1 1 calc R . . H7C H 0.8659 0.4878 0.1917 0.049 Uiso 1 1 calc R . . C8 C 0.7008(4) 0.4474(6) -0.1431(3) 0.0232(8) Uani 1 1 d . . . C9 C 0.8113(3) 0.3957(5) -0.1227(3) 0.0154(7) Uani 1 1 d . . . H9A H 0.8270 0.2673 -0.0832 0.023 Uiso 1 1 calc R . . H9B H 0.8696 0.4989 -0.0779 0.023 Uiso 1 1 calc R . . H9C H 0.8265 0.3790 -0.1906 0.023 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0253(6) 0.0264(6) 0.0308(6) -0.0055(4) 0.0165(4) -0.0019(4) O1 0.0299(16) 0.0381(18) 0.0481(19) -0.0032(14) 0.0272(15) -0.0042(13) O2 0.055(3) 0.092(4) 0.048(2) -0.016(2) 0.019(2) -0.008(3) C1 0.0206(17) 0.0219(18) 0.0234(18) -0.0014(14) 0.0092(14) 0.0014(14) C2 0.0170(16) 0.0237(18) 0.0216(17) -0.0004(14) 0.0093(14) -0.0003(14) C3 0.0218(18) 0.029(2) 0.031(2) 0.0053(16) 0.0093(16) 0.0039(16) C4 0.0261(19) 0.0218(19) 0.036(2) 0.0018(16) 0.0171(17) 0.0023(15) C5 0.028(2) 0.026(2) 0.042(2) -0.0045(17) 0.0227(18) -0.0064(16) C6 0.0173(17) 0.031(2) 0.032(2) -0.0068(16) 0.0111(15) -0.0006(15) C7 0.039(2) 0.030(2) 0.025(2) 0.0032(17) 0.0079(17) 0.0038(18) C8 0.0278(19) 0.0223(18) 0.0234(18) 0.0020(14) 0.0141(15) -0.0018(15) C9 0.0115(14) 0.0180(16) 0.0189(15) -0.0043(12) 0.0081(12) 0.0041(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.494(3) . ? S1 C4 1.835(4) . ? S1 C1 1.866(4) . ? O2 C8 1.511(6) . ? C1 C6 1.502(5) . ? C1 C7 1.514(6) . ? C1 C2 1.544(5) . ? C2 C8 1.517(5) . ? C2 C3 1.557(5) . ? C3 C4 1.543(6) . ? C4 C5 1.503(6) . ? C5 C6 1.326(6) . ? C8 C9 1.211(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 C4 110.7(2) . . ? O1 S1 C1 110.04(19) . . ? C4 S1 C1 80.81(18) . . ? C6 C1 C7 118.0(4) . . ? C6 C1 C2 110.7(3) . . ? C7 C1 C2 115.7(3) . . ? C6 C1 S1 95.9(3) . . ? C7 C1 S1 112.6(3) . . ? C2 C1 S1 100.8(2) . . ? C8 C2 C1 113.8(3) . . ? C8 C2 C3 112.6(3) . . ? C1 C2 C3 106.6(3) . . ? C4 C3 C2 105.1(3) . . ? C5 C4 C3 110.7(3) . . ? C5 C4 S1 96.3(3) . . ? C3 C4 S1 103.0(3) . . ? C6 C5 C4 110.7(4) . . ? C5 C6 C1 111.1(3) . . ? C9 C8 O2 121.9(4) . . ? C9 C8 C2 122.9(4) . . ? O2 C8 C2 115.2(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 C1 C6 164.3(3) . . . . ? C4 S1 C1 C6 55.5(3) . . . . ? O1 S1 C1 C7 -72.0(3) . . . . ? C4 S1 C1 C7 179.1(3) . . . . ? O1 S1 C1 C2 51.9(3) . . . . ? C4 S1 C1 C2 -56.9(3) . . . . ? C6 C1 C2 C8 66.6(4) . . . . ? C7 C1 C2 C8 -71.1(4) . . . . ? S1 C1 C2 C8 167.2(3) . . . . ? C6 C1 C2 C3 -58.1(4) . . . . ? C7 C1 C2 C3 164.2(3) . . . . ? S1 C1 C2 C3 42.5(3) . . . . ? C8 C2 C3 C4 -127.3(3) . . . . ? C1 C2 C3 C4 -1.9(4) . . . . ? C2 C3 C4 C5 61.3(4) . . . . ? C2 C3 C4 S1 -40.7(3) . . . . ? O1 S1 C4 C5 -164.1(3) . . . . ? C1 S1 C4 C5 -56.0(3) . . . . ? O1 S1 C4 C3 -51.1(3) . . . . ? C1 S1 C4 C3 56.9(3) . . . . ? C3 C4 C5 C6 -63.0(5) . . . . ? S1 C4 C5 C6 43.5(4) . . . . ? C4 C5 C6 C1 -0.8(5) . . . . ? C7 C1 C6 C5 -160.7(4) . . . . ? C2 C1 C6 C5 62.7(4) . . . . ? S1 C1 C6 C5 -41.3(4) . . . . ? C1 C2 C8 C9 -6.8(5) . . . . ? C3 C2 C8 C9 114.6(4) . . . . ? C1 C2 C8 O2 172.5(4) . . . . ? C3 C2 C8 O2 -66.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.909 _refine_diff_density_max 1.613 _refine_diff_density_min -0.886 _refine_diff_density_rms 0.155 #===END