# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Zhen-Jiang Liu' _publ_contact_author_email lzj5016@mail.sioc.ac.cn loop_ _publ_author_name 'Jin-Tao Liu' 'Zhen-Jiang Liu' data_cd27655 _database_code_depnum_ccdc_archive 'CCDC 691649' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 F3 N O S' _chemical_formula_weight 317.36 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' 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' 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.0128(9) _cell_length_b 8.4458(13) _cell_length_c 32.013(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1625.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1724 _cell_measurement_theta_min 4.988 _cell_measurement_theta_max 39.341 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.477 _exptl_crystal_size_mid 0.341 _exptl_crystal_size_min 0.156 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7523 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8907 _diffrn_reflns_av_R_equivalents 0.1349 _diffrn_reflns_av_sigmaI/netI 0.1297 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3183 _reflns_number_gt 1941 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0427P)^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 -0.16(13) _chemical_absolute_configuration ad _refine_ls_number_reflns 3183 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1281 _refine_ls_wR_factor_gt 0.1175 _refine_ls_goodness_of_fit_ref 0.891 _refine_ls_restrained_S_all 0.891 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.001 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 1.34113(16) 0.69668(13) 0.86598(3) 0.0639(3) Uani 1 1 d . . . O1 O 1.1839(5) 0.7951(3) 0.89004(8) 0.0947(9) Uani 1 1 d . . . N1 N 1.2224(5) 0.5386(3) 0.84400(8) 0.0556(7) Uani 1 1 d . . . F1 F 1.0042(5) 0.1865(3) 0.85591(8) 0.1048(9) Uani 1 1 d . . . F2 F 0.7916(5) 0.3251(3) 0.81667(8) 0.1033(9) Uani 1 1 d . . . F3 F 1.1330(5) 0.2932(3) 0.80078(8) 0.1086(9) Uani 1 1 d . . . C1 C 1.0543(6) 0.4648(4) 0.85816(10) 0.0499(8) Uani 1 1 d . . . C2 C 0.9204(6) 0.4964(4) 0.89477(10) 0.0515(9) Uani 1 1 d . . . H2 H 0.9651 0.5805 0.9115 0.062 Uiso 1 1 calc R . . C3 C 0.7412(5) 0.4182(4) 0.90691(10) 0.0501(9) Uani 1 1 d . . . H3 H 0.6931 0.3365 0.8897 0.060 Uiso 1 1 calc R . . C4 C 0.6110(5) 0.4471(4) 0.94471(10) 0.0448(8) Uani 1 1 d . . . C5 C 0.6863(6) 0.5476(4) 0.97674(10) 0.0548(9) Uani 1 1 d . . . H5 H 0.8217 0.5997 0.9740 0.066 Uiso 1 1 calc R . . C6 C 0.5609(6) 0.5690(4) 1.01209(11) 0.0565(9) Uani 1 1 d . . . H6 H 0.6153 0.6338 1.0332 0.068 Uiso 1 1 calc R . . C7 C 0.3573(6) 0.4977(4) 1.01721(10) 0.0519(9) Uani 1 1 d . . . C8 C 0.2807(6) 0.3993(4) 0.98553(11) 0.0558(9) Uani 1 1 d . . . H8 H 0.1433 0.3497 0.9881 0.067 Uiso 1 1 calc R . . C9 C 0.4075(5) 0.3751(4) 0.95032(10) 0.0523(9) Uani 1 1 d . . . H9 H 0.3541 0.3079 0.9296 0.063 Uiso 1 1 calc R . . C10 C 0.9950(8) 0.3161(5) 0.83244(13) 0.0747(11) Uani 1 1 d . . . C11 C 0.2184(7) 0.5262(5) 1.05594(12) 0.0731(11) Uani 1 1 d . . . H11A H 0.3133 0.5591 1.0785 0.110 Uiso 1 1 calc R . . H11B H 0.1431 0.4303 1.0636 0.110 Uiso 1 1 calc R . . H11C H 0.1108 0.6075 1.0504 0.110 Uiso 1 1 calc R . . C12 C 1.3915(5) 0.8037(5) 0.81640(10) 0.0569(9) Uani 1 1 d . . . C13 C 1.1724(7) 0.8418(5) 0.79663(13) 0.0842(13) Uani 1 1 d . . . H13A H 1.1947 0.9149 0.7741 0.116 Uiso 1 1 calc R . . H13B H 1.0757 0.8885 0.8171 0.116 Uiso 1 1 calc R . . H13C H 1.1062 0.7464 0.7861 0.116 Uiso 1 1 calc R . . C14 C 1.5422(7) 0.7047(6) 0.78951(12) 0.0920(14) Uani 1 1 d . . . H14A H 1.4575 0.6219 0.7765 0.128 Uiso 1 1 calc R . . H14B H 1.6570 0.6589 0.8065 0.128 Uiso 1 1 calc R . . H14C H 1.6084 0.7701 0.7684 0.128 Uiso 1 1 calc R . . C15 C 1.5093(7) 0.9538(5) 0.83063(13) 0.0831(13) Uani 1 1 d . . . H15A H 1.5512 1.0153 0.8067 0.115 Uiso 1 1 calc R . . H15B H 1.6400 0.9260 0.8462 0.115 Uiso 1 1 calc R . . H15C H 1.4111 1.0147 0.8480 0.115 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 0.0762(6) 0.0730(6) 0.0424(5) 0.0057(5) 0.0032(5) -0.0097(6) O1 0.134(2) 0.0824(17) 0.0682(16) -0.0253(16) 0.0462(18) -0.023(2) N1 0.0650(18) 0.0574(17) 0.0443(16) 0.0048(14) 0.0120(14) 0.0050(16) F1 0.167(2) 0.0479(12) 0.0996(18) -0.0043(14) 0.0455(18) 0.0019(16) F2 0.117(2) 0.116(2) 0.0767(16) -0.0331(16) -0.0006(15) -0.0209(19) F3 0.155(2) 0.0878(16) 0.0836(15) -0.0310(15) 0.0585(16) -0.0192(18) C1 0.065(2) 0.0460(19) 0.0391(18) 0.0030(16) 0.0094(17) 0.0054(17) C2 0.065(2) 0.0493(19) 0.0407(18) -0.0035(16) 0.0027(17) 0.0053(18) C3 0.063(2) 0.0478(19) 0.0397(19) -0.0003(15) 0.0041(16) 0.0018(19) C4 0.050(2) 0.0473(18) 0.0367(17) 0.0080(15) 0.0004(15) 0.0078(16) C5 0.060(2) 0.057(2) 0.048(2) 0.0009(17) 0.0124(18) -0.0051(19) C6 0.061(2) 0.061(2) 0.047(2) -0.0080(18) 0.0041(18) 0.0003(19) C7 0.060(2) 0.053(2) 0.0424(19) 0.0063(16) 0.0092(18) 0.0078(19) C8 0.057(2) 0.055(2) 0.056(2) 0.0099(18) 0.0037(18) -0.0009(18) C9 0.053(2) 0.065(2) 0.0384(18) 0.0014(16) -0.0038(16) -0.0010(18) C10 0.100(3) 0.062(3) 0.062(2) -0.006(2) 0.034(3) -0.001(3) C11 0.089(3) 0.075(2) 0.055(2) 0.005(2) 0.022(2) 0.000(2) C12 0.060(2) 0.069(2) 0.0422(18) 0.0043(19) 0.0102(16) -0.012(2) C13 0.092(3) 0.085(3) 0.076(3) 0.011(2) -0.021(3) -0.011(3) C14 0.094(3) 0.104(3) 0.078(3) -0.006(3) 0.042(2) -0.005(3) C15 0.101(3) 0.081(3) 0.067(3) 0.005(2) -0.007(3) -0.032(3) _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 1.476(3) . ? S1 N1 1.670(3) . ? S1 C12 1.852(3) . ? N1 C1 1.271(4) . ? F1 C10 1.328(5) . ? F2 C10 1.326(5) . ? F3 C10 1.324(4) . ? C1 C2 1.446(4) . ? C1 C10 1.544(5) . ? C2 C3 1.323(4) . ? C2 H2 0.9300 . ? C3 C4 1.462(4) . ? C3 H3 0.9300 . ? C4 C9 1.379(4) . ? C4 C5 1.406(5) . ? C5 C6 1.372(5) . ? C5 H5 0.9300 . ? C6 C7 1.374(5) . ? C6 H6 0.9300 . ? C7 C8 1.389(5) . ? C7 C11 1.514(5) . ? C8 C9 1.376(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.497(5) . ? C12 C14 1.504(5) . ? C12 C15 1.522(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? 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 N1 113.36(15) . . ? O1 S1 C12 106.09(17) . . ? N1 S1 C12 95.68(15) . . ? C1 N1 S1 125.6(2) . . ? N1 C1 C2 129.9(3) . . ? N1 C1 C10 113.1(3) . . ? C2 C1 C10 117.0(3) . . ? C3 C2 C1 126.8(3) . . ? C3 C2 H2 116.6 . . ? C1 C2 H2 116.6 . . ? C2 C3 C4 126.6(3) . . ? C2 C3 H3 116.7 . . ? C4 C3 H3 116.7 . . ? C9 C4 C5 117.2(3) . . ? C9 C4 C3 120.6(3) . . ? C5 C4 C3 122.2(3) . . ? C6 C5 C4 120.3(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 122.0(3) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C6 C7 C8 118.1(3) . . ? C6 C7 C11 121.3(3) . . ? C8 C7 C11 120.7(3) . . ? C9 C8 C7 120.2(3) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C4 122.2(3) . . ? C8 C9 H9 118.9 . . ? C4 C9 H9 118.9 . . ? F3 C10 F2 107.2(4) . . ? F3 C10 F1 106.7(4) . . ? F2 C10 F1 107.5(4) . . ? F3 C10 C1 112.5(4) . . ? F2 C10 C1 111.7(4) . . ? F1 C10 C1 111.0(3) . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C14 114.1(3) . . ? C13 C12 C15 111.0(3) . . ? C14 C12 C15 110.7(3) . . ? C13 C12 S1 108.9(2) . . ? C14 C12 S1 108.5(3) . . ? C15 C12 S1 103.1(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? 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 N1 C1 -29.5(3) . . . . ? C12 S1 N1 C1 -139.8(3) . . . . ? S1 N1 C1 C2 1.7(5) . . . . ? S1 N1 C1 C10 -175.7(3) . . . . ? N1 C1 C2 C3 177.1(3) . . . . ? C10 C1 C2 C3 -5.6(5) . . . . ? C1 C2 C3 C4 177.7(3) . . . . ? C2 C3 C4 C9 169.2(3) . . . . ? C2 C3 C4 C5 -11.2(5) . . . . ? C9 C4 C5 C6 1.0(5) . . . . ? C3 C4 C5 C6 -178.7(3) . . . . ? C4 C5 C6 C7 -1.6(5) . . . . ? C5 C6 C7 C8 1.0(5) . . . . ? C5 C6 C7 C11 -178.3(3) . . . . ? C6 C7 C8 C9 0.2(5) . . . . ? C11 C7 C8 C9 179.5(3) . . . . ? C7 C8 C9 C4 -0.7(5) . . . . ? C5 C4 C9 C8 0.2(5) . . . . ? C3 C4 C9 C8 179.8(3) . . . . ? N1 C1 C10 F3 0.8(5) . . . . ? C2 C1 C10 F3 -177.0(3) . . . . ? N1 C1 C10 F2 -119.8(3) . . . . ? C2 C1 C10 F2 62.4(4) . . . . ? N1 C1 C10 F1 120.2(4) . . . . ? C2 C1 C10 F1 -57.6(5) . . . . ? O1 S1 C12 C13 -52.5(3) . . . . ? N1 S1 C12 C13 63.9(3) . . . . ? O1 S1 C12 C14 -177.2(3) . . . . ? N1 S1 C12 C14 -60.8(3) . . . . ? O1 S1 C12 C15 65.4(3) . . . . ? N1 S1 C12 C15 -178.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.246 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.050 # Attachment 'cd28144.cif' data_cd28144 _database_code_depnum_ccdc_archive 'CCDC 691650' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H17 Cl F3 N O S' _chemical_formula_weight 339.80 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' N N 0.0061 0.0033 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.8166(6) _cell_length_b 14.9426(16) _cell_length_c 18.2981(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1590.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2620 _cell_measurement_theta_min 5.221 _cell_measurement_theta_max 45.607 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.407 _exptl_crystal_size_mid 0.258 _exptl_crystal_size_min 0.191 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.399 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.77081 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8401 _diffrn_reflns_av_R_equivalents 0.1417 _diffrn_reflns_av_sigmaI/netI 0.0957 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2948 _reflns_number_gt 2492 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0425P)^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 mixed _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 0.09(10) _chemical_absolute_configuration ad _refine_ls_number_reflns 2948 _refine_ls_number_parameters 197 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1147 _refine_ls_wR_factor_gt 0.1108 _refine_ls_goodness_of_fit_ref 0.971 _refine_ls_restrained_S_all 0.971 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.001 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 0.43807(12) 0.17673(5) 0.94052(4) 0.0354(2) Uani 1 1 d . . . Cl1 Cl 1.1035(2) 0.83126(6) 0.87910(6) 0.0800(4) Uani 1 1 d . . . F1 F 0.1940(4) 0.24624(14) 0.80111(12) 0.0772(7) Uani 1 1 d . . . F2 F 0.4770(5) 0.30405(17) 0.74506(11) 0.0880(8) Uani 1 1 d . . . F3 F 0.1989(4) 0.38660(16) 0.78000(13) 0.0813(7) Uani 1 1 d . . . N1 N 0.5789(5) 0.25468(16) 0.89295(13) 0.0395(6) Uani 1 1 d D . . O1 O 0.4978(3) 0.18542(14) 1.01927(10) 0.0441(5) Uani 1 1 d . . . C1 C 0.4481(5) 0.33457(18) 0.87154(16) 0.0401(7) Uani 1 1 d . . . H1 H 0.3308 0.3469 0.9086 0.048 Uiso 1 1 calc R . . C2 C 0.6057(6) 0.4138(2) 0.86536(17) 0.0453(8) Uani 1 1 d . . . H2 H 0.7498 0.4056 0.8444 0.054 Uiso 1 1 calc R . . C3 C 0.5490(6) 0.49416(19) 0.88828(16) 0.0477(8) Uani 1 1 d . . . H3 H 0.4047 0.5003 0.9096 0.057 Uiso 1 1 calc R . . C4 C 0.6916(6) 0.5758(2) 0.88345(17) 0.0449(8) Uani 1 1 d . . . C5 C 0.6166(6) 0.6519(2) 0.9199(2) 0.0552(9) Uani 1 1 d . . . H5 H 0.4782 0.6501 0.9453 0.066 Uiso 1 1 calc R . . C6 C 0.7425(7) 0.7301(2) 0.9193(2) 0.0617(10) Uani 1 1 d . . . H6 H 0.6906 0.7803 0.9445 0.074 Uiso 1 1 calc R . . C7 C 0.9441(7) 0.7330(2) 0.88136(17) 0.0517(8) Uani 1 1 d . . . C8 C 1.0232(7) 0.6594(2) 0.84367(19) 0.0546(9) Uani 1 1 d . . . H8 H 1.1602 0.6622 0.8176 0.066 Uiso 1 1 calc R . . C9 C 0.8964(6) 0.5817(2) 0.84528(19) 0.0531(9) Uani 1 1 d . . . H9 H 0.9498 0.5318 0.8200 0.064 Uiso 1 1 calc R . . C10 C 0.3319(6) 0.3174(3) 0.79908(18) 0.0539(9) Uani 1 1 d . . . C12 C 0.5980(6) 0.0775(2) 0.90774(18) 0.0438(7) Uani 1 1 d . . . C13 C 0.8524(5) 0.0905(2) 0.9153(2) 0.0568(9) Uani 1 1 d . . . H13A H 0.8883 0.1066 0.9647 0.085 Uiso 1 1 calc R . . H13B H 0.9019 0.1373 0.8829 0.085 Uiso 1 1 calc R . . H13C H 0.9301 0.0358 0.9029 0.085 Uiso 1 1 calc R . . C14 C 0.5119(7) 0.0015(2) 0.9559(2) 0.0645(11) Uani 1 1 d . . . H14A H 0.3484 -0.0044 0.9504 0.097 Uiso 1 1 calc R . . H14B H 0.5478 0.0142 1.0060 0.097 Uiso 1 1 calc R . . H14C H 0.5851 -0.0534 0.9416 0.097 Uiso 1 1 calc R . . C15 C 0.5228(8) 0.0628(2) 0.8289(2) 0.0744(12) Uani 1 1 d . . . H15A H 0.5874 0.0078 0.8111 0.112 Uiso 1 1 calc R . . H15B H 0.5756 0.1116 0.7992 0.112 Uiso 1 1 calc R . . H15C H 0.3581 0.0595 0.8267 0.112 Uiso 1 1 calc R . . H1A H 0.712(4) 0.2675(19) 0.9091(15) 0.040(9) Uiso 1 1 d 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 0.0369(4) 0.0294(3) 0.0399(4) -0.0017(3) 0.0002(3) -0.0038(4) Cl1 0.1033(8) 0.0504(6) 0.0863(7) -0.0033(5) -0.0021(6) -0.0292(6) F1 0.0897(17) 0.0688(15) 0.0729(13) 0.0080(13) -0.0315(13) -0.0314(14) F2 0.1061(18) 0.114(2) 0.0441(11) -0.0075(12) 0.0035(13) -0.0074(18) F3 0.0895(17) 0.0709(16) 0.0836(15) 0.0262(13) -0.0316(14) 0.0035(14) N1 0.0360(15) 0.0362(14) 0.0464(14) 0.0013(11) -0.0009(14) -0.0068(13) O1 0.0513(13) 0.0424(12) 0.0388(11) -0.0023(10) 0.0002(10) 0.0022(10) C1 0.0431(16) 0.0349(16) 0.0421(15) 0.0008(13) 0.0016(15) -0.0021(16) C2 0.050(2) 0.0352(17) 0.0506(17) 0.0042(15) 0.0049(16) -0.0009(15) C3 0.0539(19) 0.0387(17) 0.0505(17) 0.0030(14) -0.0018(17) -0.0037(17) C4 0.053(2) 0.0341(17) 0.0474(18) 0.0037(15) -0.0063(16) 0.0010(15) C5 0.062(2) 0.047(2) 0.057(2) -0.0066(16) 0.0049(18) -0.0003(17) C6 0.079(3) 0.0406(19) 0.066(2) -0.0120(19) -0.001(2) -0.0047(19) C7 0.066(2) 0.0389(17) 0.0498(18) 0.0027(15) -0.009(2) -0.0073(18) C8 0.059(2) 0.050(2) 0.0553(19) 0.0068(16) 0.0006(17) -0.0043(17) C9 0.065(2) 0.0368(18) 0.0574(19) -0.0033(16) 0.0041(19) 0.0006(17) C10 0.058(2) 0.057(2) 0.0465(19) 0.0089(19) -0.0051(16) -0.008(2) C12 0.0474(19) 0.0314(16) 0.0526(17) -0.0092(14) 0.0019(16) 0.0006(14) C13 0.049(2) 0.0410(19) 0.080(2) -0.0047(19) 0.0063(18) 0.0043(16) C14 0.067(3) 0.0300(17) 0.096(3) 0.0032(19) 0.004(2) 0.0003(17) C15 0.095(3) 0.060(2) 0.069(2) -0.033(2) -0.001(2) 0.004(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 S1 O1 1.488(2) . ? S1 N1 1.669(3) . ? S1 C12 1.850(3) . ? Cl1 C7 1.737(3) . ? F1 C10 1.332(4) . ? F2 C10 1.315(4) . ? F3 C10 1.338(4) . ? N1 C1 1.469(4) . ? N1 H1A 0.852(18) . ? C1 C2 1.501(4) . ? C1 C10 1.510(4) . ? C1 H1 0.9800 . ? C2 C3 1.314(4) . ? C2 H2 0.9300 . ? C3 C4 1.478(4) . ? C3 H3 0.9300 . ? C4 C9 1.384(5) . ? C4 C5 1.389(4) . ? C5 C6 1.379(5) . ? C5 H5 0.9300 . ? C6 C7 1.363(5) . ? C6 H6 0.9300 . ? C7 C8 1.378(5) . ? C8 C9 1.375(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C12 C13 1.499(4) . ? C12 C14 1.523(5) . ? C12 C15 1.524(5) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? 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 N1 109.24(13) . . ? O1 S1 C12 105.45(14) . . ? N1 S1 C12 98.22(14) . . ? C1 N1 S1 116.9(2) . . ? C1 N1 H1A 112(2) . . ? S1 N1 H1A 115(2) . . ? N1 C1 C2 110.2(2) . . ? N1 C1 C10 109.1(3) . . ? C2 C1 C10 110.0(3) . . ? N1 C1 H1 109.2 . . ? C2 C1 H1 109.2 . . ? C10 C1 H1 109.2 . . ? C3 C2 C1 122.9(3) . . ? C3 C2 H2 118.5 . . ? C1 C2 H2 118.5 . . ? C2 C3 C4 126.5(3) . . ? C2 C3 H3 116.8 . . ? C4 C3 H3 116.8 . . ? C9 C4 C5 117.4(3) . . ? C9 C4 C3 124.5(3) . . ? C5 C4 C3 118.1(3) . . ? C6 C5 C4 121.6(3) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C7 C6 C5 119.2(3) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C8 121.1(3) . . ? C6 C7 Cl1 119.9(3) . . ? C8 C7 Cl1 119.0(3) . . ? C9 C8 C7 118.9(3) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C8 C9 C4 121.8(3) . . ? C8 C9 H9 119.1 . . ? C4 C9 H9 119.1 . . ? F2 C10 F1 106.7(3) . . ? F2 C10 F3 107.0(3) . . ? F1 C10 F3 106.0(3) . . ? F2 C10 C1 113.5(3) . . ? F1 C10 C1 112.4(3) . . ? F3 C10 C1 110.9(3) . . ? C13 C12 C14 111.6(3) . . ? C13 C12 C15 112.9(3) . . ? C14 C12 C15 110.2(3) . . ? C13 C12 S1 111.3(2) . . ? C14 C12 S1 104.2(2) . . ? C15 C12 S1 106.2(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? 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 N1 C1 -100.9(2) . . . . ? C12 S1 N1 C1 149.5(2) . . . . ? S1 N1 C1 C2 151.1(2) . . . . ? S1 N1 C1 C10 -88.0(3) . . . . ? N1 C1 C2 C3 -139.6(3) . . . . ? C10 C1 C2 C3 100.1(4) . . . . ? C1 C2 C3 C4 -179.1(3) . . . . ? C2 C3 C4 C9 8.7(5) . . . . ? C2 C3 C4 C5 -171.0(3) . . . . ? C9 C4 C5 C6 -1.1(5) . . . . ? C3 C4 C5 C6 178.6(3) . . . . ? C4 C5 C6 C7 0.8(6) . . . . ? C5 C6 C7 C8 0.1(5) . . . . ? C5 C6 C7 Cl1 179.3(3) . . . . ? C6 C7 C8 C9 -0.6(5) . . . . ? Cl1 C7 C8 C9 -179.8(3) . . . . ? C7 C8 C9 C4 0.2(5) . . . . ? C5 C4 C9 C8 0.6(5) . . . . ? C3 C4 C9 C8 -179.1(3) . . . . ? N1 C1 C10 F2 -63.6(4) . . . . ? C2 C1 C10 F2 57.4(4) . . . . ? N1 C1 C10 F1 57.5(4) . . . . ? C2 C1 C10 F1 178.5(3) . . . . ? N1 C1 C10 F3 176.0(3) . . . . ? C2 C1 C10 F3 -63.0(3) . . . . ? O1 S1 C12 C13 -61.6(3) . . . . ? N1 S1 C12 C13 51.1(3) . . . . ? O1 S1 C12 C14 58.8(3) . . . . ? N1 S1 C12 C14 171.5(2) . . . . ? O1 S1 C12 C15 175.2(2) . . . . ? N1 S1 C12 C15 -72.1(3) . . . . ? 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_site_symmetry_A N1 H1A O1 0.852(18) 2.230(19) 3.052(3) 162(3) 4_557 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.456 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.062