# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_global _publ_contact_author_email JIANGB@PUB.SIOC.AC.CN _publ_contact_author_name 'Prof Biao Jiang' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Biao Jiang' 'Wennan Xiong' 'Fangjiang Zhang' data_shelxs _database_code_CSD 196988 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H8 F3 N O2 S' _chemical_formula_weight 275.24 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c 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' '-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 22.596(8) _cell_length_b 5.881(3) _cell_length_c 20.446(7) _cell_angle_alpha 90.00 _cell_angle_beta 118.55(3) _cell_angle_gamma 90.00 _cell_volume 2386.7(17) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14 _cell_measurement_theta_min 18.4 _cell_measurement_theta_max 21.7 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.303 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8567 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type afc7r _diffrn_measurement_method 'omega/2theta scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time -0.01 _diffrn_standards_decay_% ? _diffrn_reflns_number 2074 _diffrn_reflns_av_R_equivalents 0.0828 _diffrn_reflns_av_sigmaI/netI 0.0942 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2030 _reflns_number_gt 1657 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0732P)^2^+1.8652P] 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 SHELXL _refine_ls_extinction_coef 0.0032(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2030 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0734 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1362 _refine_ls_wR_factor_gt 0.1261 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.042 _refine_ls_shift/su_mean 0.007 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 0.18659(3) 0.91020(10) 0.05342(3) 0.0353(3) Uani 1 1 d . . . O1 O 0.18701(9) 0.6680(4) 0.04417(10) 0.0514(5) Uani 1 1 d . . . O2 O 0.17993(9) 1.0591(4) -0.00515(9) 0.0512(5) Uani 1 1 d . . . N1 N 0.29042(14) 0.7426(5) 0.24907(14) 0.0694(8) Uani 1 1 d . . . F1 F 0.43137(10) 1.0589(6) 0.14160(15) 0.1265(12) Uani 1 1 d . . . F2 F 0.41297(9) 0.9907(4) 0.23294(10) 0.0821(7) Uani 1 1 d . . . F3 F 0.39440(10) 0.7399(4) 0.15208(14) 0.0962(8) Uani 1 1 d . . . C1 C 0.26498(10) 0.9825(4) 0.13293(12) 0.0334(5) Uani 1 1 d . . . C2 C 0.32001(12) 1.0497(5) 0.11433(15) 0.0447(6) Uani 1 1 d . . . C3 C 0.28993(14) 1.2243(4) 0.14135(16) 0.0461(6) Uani 1 1 d . . . C4 C 0.27998(11) 0.8485(5) 0.19792(14) 0.0426(6) Uani 1 1 d . . . C5 C 0.38965(13) 0.9617(7) 0.16048(17) 0.0629(9) Uani 1 1 d . . . C6 C 0.12485(10) 0.9775(4) 0.07937(12) 0.0353(5) Uani 1 1 d . . . C7 C 0.09292(13) 1.1872(5) 0.05869(15) 0.0478(6) Uani 1 1 d . . . C8 C 0.04256(15) 1.2326(6) 0.07707(19) 0.0611(8) Uani 1 1 d . . . C9 C 0.02650(14) 1.0772(7) 0.11557(19) 0.0650(9) Uani 1 1 d . . . C10 C 0.05891(14) 0.8709(6) 0.13646(18) 0.0605(8) Uani 1 1 d . . . C11 C 0.10894(12) 0.8194(5) 0.11807(15) 0.0464(6) Uani 1 1 d . . . H1 H 0.3080(14) 1.034(5) 0.0629(17) 0.052(8) Uiso 1 1 d . . . H2 H 0.3131(13) 1.274(5) 0.1925(16) 0.043(7) Uiso 1 1 d . . . H3 H 0.2613(16) 1.342(6) 0.1090(18) 0.062(9) Uiso 1 1 d . . . H4 H 0.1037(16) 1.288(6) 0.0318(18) 0.060(9) Uiso 1 1 d . . . H5 H 0.0182(15) 1.379(6) 0.0631(17) 0.060(8) Uiso 1 1 d . . . H6 H -0.0067(19) 1.104(7) 0.127(2) 0.083(11) Uiso 1 1 d . . . H7 H 0.0450(19) 0.758(6) 0.164(2) 0.085(11) Uiso 1 1 d . . . H8 H 0.1331(15) 0.675(6) 0.1299(16) 0.058(8) 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 S1 0.0380(4) 0.0384(4) 0.0313(4) -0.0011(2) 0.0179(3) 0.0012(2) O1 0.0549(10) 0.0456(11) 0.0563(11) -0.0128(8) 0.0286(9) 0.0005(8) O2 0.0539(10) 0.0672(12) 0.0341(10) 0.0101(8) 0.0222(8) 0.0017(9) N1 0.0700(17) 0.0834(19) 0.0507(15) 0.0270(14) 0.0255(14) 0.0074(13) F1 0.0516(11) 0.197(3) 0.145(2) 0.042(2) 0.0577(14) -0.0025(14) F2 0.0515(9) 0.1130(18) 0.0578(12) -0.0146(11) 0.0067(8) 0.0094(10) F3 0.0686(12) 0.1048(18) 0.1003(16) -0.0209(14) 0.0285(12) 0.0352(11) C1 0.0353(11) 0.0375(12) 0.0300(12) 0.0006(9) 0.0178(9) 0.0049(9) C2 0.0414(12) 0.0560(15) 0.0427(15) -0.0003(11) 0.0249(11) -0.0021(11) C3 0.0492(14) 0.0385(13) 0.0482(17) 0.0001(11) 0.0213(13) -0.0011(11) C4 0.0411(12) 0.0456(13) 0.0408(14) 0.0044(11) 0.0193(11) 0.0025(10) C5 0.0397(14) 0.090(2) 0.062(2) -0.0102(17) 0.0267(14) 0.0013(14) C6 0.0317(10) 0.0392(12) 0.0318(12) -0.0027(9) 0.0126(9) -0.0014(9) C7 0.0466(14) 0.0427(14) 0.0515(16) 0.0024(11) 0.0214(13) 0.0042(11) C8 0.0491(15) 0.0561(17) 0.075(2) -0.0071(15) 0.0274(15) 0.0132(13) C9 0.0436(14) 0.088(2) 0.071(2) -0.0129(17) 0.0343(15) 0.0012(14) C10 0.0502(15) 0.080(2) 0.0595(18) 0.0066(16) 0.0331(14) -0.0052(14) C11 0.0406(13) 0.0506(15) 0.0488(15) 0.0061(12) 0.0220(12) -0.0012(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4328(19) . ? S1 O1 1.437(2) . ? S1 C6 1.758(2) . ? S1 C1 1.791(2) . ? N1 C4 1.141(4) . ? F1 C5 1.308(4) . ? F2 C5 1.325(4) . ? F3 C5 1.327(4) . ? C1 C4 1.440(3) . ? C1 C3 1.509(3) . ? C1 C2 1.516(3) . ? C2 C3 1.476(4) . ? C2 C5 1.488(4) . ? C6 C11 1.376(3) . ? C6 C7 1.389(3) . ? C7 C8 1.384(4) . ? C8 C9 1.364(5) . ? C9 C10 1.376(5) . ? C10 C11 1.384(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 120.05(12) . . ? O2 S1 C6 109.46(11) . . ? O1 S1 C6 108.58(11) . . ? O2 S1 C1 106.08(11) . . ? O1 S1 C1 106.75(11) . . ? C6 S1 C1 104.84(10) . . ? C4 C1 C3 120.1(2) . . ? C4 C1 C2 120.98(19) . . ? C3 C1 C2 58.43(17) . . ? C4 C1 S1 113.72(17) . . ? C3 C1 S1 118.70(17) . . ? C2 C1 S1 114.08(16) . . ? C3 C2 C5 122.8(3) . . ? C3 C2 C1 60.53(16) . . ? C5 C2 C1 119.7(2) . . ? C2 C3 C1 61.04(16) . . ? N1 C4 C1 178.5(3) . . ? F1 C5 F2 108.5(3) . . ? F1 C5 F3 106.1(3) . . ? F2 C5 F3 104.9(3) . . ? F1 C5 C2 110.7(3) . . ? F2 C5 C2 113.5(2) . . ? F3 C5 C2 112.7(3) . . ? C11 C6 C7 122.4(2) . . ? C11 C6 S1 118.99(18) . . ? C7 C6 S1 118.65(19) . . ? C8 C7 C6 117.6(3) . . ? C9 C8 C7 120.5(3) . . ? C8 C9 C10 121.4(3) . . ? C9 C10 C11 119.4(3) . . ? C6 C11 C10 118.7(3) . . ? _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.914 _refine_diff_density_max 0.511 _refine_diff_density_min -0.651 _refine_diff_density_rms 0.077