data_3a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H8 Cl F O S' _chemical_formula_sum 'C13 H8 Cl F O S' _chemical_formula_weight 266.70 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' '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_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 27.963(9) _cell_length_b 3.9233(15) _cell_length_c 11.146(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1222.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1849 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 22.39 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.93 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.474 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.6683 _exptl_absorpt_correction_T_max 0.9749 _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 APEX Duo CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 8618 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0664 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 29.94 _reflns_number_total 3368 _reflns_number_gt 1899 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 2009) ; _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. ; _iucr_refine_instructions_details ; TITL mo_ch1_0m in Pca2(1) (RT) CELL 0.71073 27.9628 3.9233 11.1457 90.000 90.000 90.000 ZERR 4.00 0.0090 0.0015 0.0038 0.000 0.000 0.000 LATT -1 SYMM -X, -Y, 0.5+Z SYMM 0.5+X, -Y, Z SYMM 0.5-X, Y, 0.5+Z SFAC C H O F S Cl UNIT 52 32 4 4 4 4 SIZE 0.183 0.925 0.054 L.S. 10 BOND $H FMAP 2 2 60 PLAN 20 ACTA CONF WGHT 0.0599 0.0000 FVAR 0.53292 CL1 6 0.672422 -0.244870 -0.031772 11.00000 0.05626 0.08892 = 0.13125 0.00880 0.00610 0.00589 S1 5 0.586696 0.059427 0.083757 11.00000 0.06425 0.08017 = 0.06208 0.00241 -0.00469 0.00100 F1 4 0.333581 0.739430 0.162199 11.00000 0.08359 0.24097 = 0.09170 -0.04592 0.01100 0.02886 O1 3 0.498901 0.387385 0.167886 11.00000 0.08641 0.10672 = 0.06040 -0.00978 0.01219 0.00871 C1 1 0.615258 -0.088075 -0.041256 11.00000 0.05549 0.05584 = 0.08403 0.00811 0.00777 -0.00494 C2 1 0.588215 -0.065314 -0.141882 11.00000 0.07192 0.08437 = 0.06646 -0.00319 0.01505 0.00920 AFIX 43 H2A 2 0.598318 -0.135186 -0.217478 11.00000 -1.20000 AFIX 0 C3 1 0.543397 0.075613 -0.118281 11.00000 0.06276 0.07784 = 0.05533 -0.00500 -0.00072 0.00755 AFIX 43 H3A 2 0.520241 0.109815 -0.176953 11.00000 -1.20000 AFIX 0 C4 1 0.536912 0.158540 -0.000085 11.00000 0.05783 0.04860 = 0.05579 0.00155 0.00418 -0.00143 C5 1 0.496290 0.313723 0.060718 11.00000 0.06229 0.05673 = 0.05649 0.00319 0.01046 -0.00251 C6 1 0.452635 0.382453 -0.011009 11.00000 0.05915 0.06819 = 0.06336 0.00229 0.00811 0.00461 AFIX 43 H6A 2 0.452778 0.333237 -0.092630 11.00000 -1.20000 AFIX 0 C7 1 0.413730 0.511045 0.037580 11.00000 0.06164 0.06499 = 0.07074 0.00864 0.00987 0.00048 AFIX 43 H7A 2 0.415402 0.560479 0.119078 11.00000 -1.20000 AFIX 0 C8 1 0.368107 0.585609 -0.021381 11.00000 0.05956 0.05743 = 0.07624 0.00182 0.01199 0.00082 C9 1 0.360715 0.542803 -0.144411 11.00000 0.07013 0.09825 = 0.07849 -0.00065 0.01060 0.01368 AFIX 43 H9A 2 0.385736 0.464376 -0.191949 11.00000 -1.20000 AFIX 0 C10 1 0.317615 0.613351 -0.196641 11.00000 0.09101 0.12300 = 0.07924 0.00464 -0.00163 0.02488 AFIX 43 H10A 2 0.313963 0.589248 -0.279142 11.00000 -1.20000 AFIX 0 C11 1 0.279469 0.720204 -0.127578 11.00000 0.07025 0.09232 = 0.11010 0.01038 -0.00470 0.00988 AFIX 43 H11A 2 0.249930 0.759921 -0.163282 11.00000 -1.20000 AFIX 0 C12 1 0.284967 0.767622 -0.007324 11.00000 0.06048 0.11212 = 0.09964 -0.00795 0.01741 0.00224 AFIX 43 H12A 2 0.259904 0.846719 0.039932 11.00000 -1.20000 AFIX 0 C13 1 0.328853 0.694444 0.041666 11.00000 0.06163 0.10293 = 0.07870 -0.00413 0.01231 0.00291 HKLF 4 1 0 0 1 0 -1 0 1 0 0 REM mo_ch1_0m in Pca2(1) (RT) REM R1 = 0.0490 for 1899 Fo > 4sig(Fo) and 0.0974 for all 3368 data REM 154 parameters refined using 1 restraints END WGHT 0.0599 0.0000 REM Highest difference peak 0.197, deepest hole -0.228, 1-sigma level 0.052 Q1 1 0.6346 -0.0406 -0.0382 11.00000 0.05 0.20 Q2 1 0.6665 -0.0493 0.0238 11.00000 0.05 0.19 Q3 1 0.5648 0.2432 0.0347 11.00000 0.05 0.19 Q4 1 0.6054 -0.2237 -0.0576 11.00000 0.05 0.18 Q5 1 0.3230 0.4610 0.1238 11.00000 0.05 0.18 Q6 1 0.5804 -0.2781 0.0358 11.00000 0.05 0.16 Q7 1 0.6185 0.2953 0.0018 11.00000 0.05 0.16 Q8 1 0.7330 -0.2486 -0.0366 11.00000 0.05 0.16 Q9 1 0.5215 0.5972 0.1078 11.00000 0.05 0.16 Q10 1 0.5995 -0.1751 0.0153 11.00000 0.05 0.16 Q11 1 0.6930 -0.0824 0.0292 11.00000 0.05 0.16 Q12 1 0.6332 -0.5053 -0.0235 11.00000 0.05 0.15 Q13 1 0.5254 0.0509 0.1046 11.00000 0.05 0.15 Q14 1 0.3787 0.4080 0.0211 11.00000 0.05 0.15 Q15 1 0.3364 0.5178 0.1080 11.00000 0.05 0.15 Q16 1 0.4175 0.2428 0.1185 11.00000 0.05 0.14 Q17 1 0.7071 -0.0145 -0.0443 11.00000 0.05 0.14 Q18 1 0.4557 0.7839 0.0158 11.00000 0.05 0.14 Q19 1 0.5234 0.2721 0.0350 11.00000 0.05 0.14 Q20 1 0.5403 0.2464 -0.0453 11.00000 0.05 0.14 ; _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^)+(0.0599P)^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 0.02(10) _refine_ls_number_reflns 3368 _refine_ls_number_parameters 154 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0974 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1363 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.989 _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 Cl1 Cl 0.67242(3) -0.2449(3) -0.03177(14) 0.0921(4) Uani 1 1 d . . . S1 S 0.58670(3) 0.0594(2) 0.08376(7) 0.0688(3) Uani 1 1 d . . . F1 F 0.33358(10) 0.7394(12) 0.1622(3) 0.1388(15) Uani 1 1 d . . . O1 O 0.49890(9) 0.3874(8) 0.1679(2) 0.0845(8) Uani 1 1 d . . . C1 C 0.61526(11) -0.0881(8) -0.0413(3) 0.0651(8) Uani 1 1 d . . . C2 C 0.58821(13) -0.0653(10) -0.1419(3) 0.0743(10) Uani 1 1 d . . . H2A H 0.5983 -0.1352 -0.2175 0.089 Uiso 1 1 calc R . . C3 C 0.54340(12) 0.0756(10) -0.1183(3) 0.0653(8) Uani 1 1 d . . . H3A H 0.5202 0.1098 -0.1770 0.078 Uiso 1 1 calc R . . C4 C 0.53691(11) 0.1585(8) -0.0001(3) 0.0541(7) Uani 1 1 d . . . C5 C 0.49629(11) 0.3137(9) 0.0607(3) 0.0585(8) Uani 1 1 d . . . C6 C 0.45264(11) 0.3825(9) -0.0110(3) 0.0636(8) Uani 1 1 d . . . H6A H 0.4528 0.3332 -0.0926 0.076 Uiso 1 1 calc R . . C7 C 0.41373(11) 0.5110(9) 0.0376(3) 0.0658(9) Uani 1 1 d . . . H7A H 0.4154 0.5605 0.1191 0.079 Uiso 1 1 calc R . . C8 C 0.36811(11) 0.5856(9) -0.0214(3) 0.0644(8) Uani 1 1 d . . . C9 C 0.36072(14) 0.5428(12) -0.1444(4) 0.0823(11) Uani 1 1 d . . . H9A H 0.3857 0.4644 -0.1919 0.099 Uiso 1 1 calc R . . C10 C 0.31761(17) 0.6134(15) -0.1966(4) 0.0978(14) Uani 1 1 d . . . H10A H 0.3140 0.5892 -0.2791 0.117 Uiso 1 1 calc R . . C11 C 0.27947(14) 0.7202(12) -0.1276(4) 0.0909(13) Uani 1 1 d . . . H11A H 0.2499 0.7599 -0.1633 0.109 Uiso 1 1 calc R . . C12 C 0.28497(13) 0.7676(12) -0.0073(4) 0.0907(12) Uani 1 1 d . . . H12A H 0.2599 0.8467 0.0399 0.109 Uiso 1 1 calc R . . C13 C 0.32885(13) 0.6944(13) 0.0417(4) 0.0811(12) 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 Cl1 0.0563(4) 0.0889(7) 0.1313(9) 0.0088(7) 0.0061(6) 0.0059(5) S1 0.0643(5) 0.0802(6) 0.0621(4) 0.0024(6) -0.0047(4) 0.0010(4) F1 0.0836(17) 0.241(4) 0.0917(18) -0.046(2) 0.0110(13) 0.029(2) O1 0.0864(17) 0.107(2) 0.0604(13) -0.0098(16) 0.0122(12) 0.0087(15) C1 0.0555(15) 0.0558(19) 0.084(2) 0.008(2) 0.0078(17) -0.0049(14) C2 0.072(2) 0.084(3) 0.0665(17) -0.0032(19) 0.0151(17) 0.0092(19) C3 0.0628(18) 0.078(2) 0.0553(16) -0.0050(17) -0.0007(13) 0.0075(17) C4 0.0578(15) 0.0486(17) 0.0558(15) 0.0015(14) 0.0042(13) -0.0014(14) C5 0.0623(18) 0.0567(19) 0.0565(17) 0.0032(15) 0.0105(13) -0.0025(14) C6 0.0592(16) 0.068(2) 0.0634(16) 0.0023(17) 0.0081(15) 0.0046(15) C7 0.0616(19) 0.065(2) 0.0707(18) 0.0086(16) 0.0099(15) 0.0005(16) C8 0.0596(15) 0.057(2) 0.076(2) 0.002(2) 0.0120(17) 0.0008(14) C9 0.070(2) 0.098(3) 0.078(2) -0.001(2) 0.0106(19) 0.014(2) C10 0.091(3) 0.123(4) 0.079(2) 0.005(3) -0.002(2) 0.025(3) C11 0.070(2) 0.092(3) 0.110(3) 0.010(3) -0.005(2) 0.010(2) C12 0.0605(19) 0.112(3) 0.100(3) -0.008(3) 0.017(2) 0.002(2) C13 0.062(2) 0.103(3) 0.079(2) -0.004(2) 0.0123(16) 0.003(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 Cl1 C1 1.716(3) . ? S1 C1 1.707(4) . ? S1 C4 1.721(3) . ? F1 C13 1.361(5) . ? O1 C5 1.231(4) . ? C1 C2 1.356(5) . ? C2 C3 1.395(5) . ? C2 H2A 0.9300 . ? C3 C4 1.369(4) . ? C3 H3A 0.9300 . ? C4 C5 1.456(4) . ? C5 C6 1.484(5) . ? C6 C7 1.316(4) . ? C6 H6A 0.9300 . ? C7 C8 1.465(5) . ? C7 H7A 0.9300 . ? C8 C13 1.371(5) . ? C8 C9 1.397(5) . ? C9 C10 1.367(6) . ? C9 H9A 0.9300 . ? C10 C11 1.381(6) . ? C10 H10A 0.9300 . ? C11 C12 1.362(6) . ? C11 H11A 0.9300 . ? C12 C13 1.374(5) . ? C12 H12A 0.9300 . ? 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 S1 C4 90.68(16) . . ? C2 C1 S1 113.1(2) . . ? C2 C1 Cl1 126.5(3) . . ? S1 C1 Cl1 120.5(2) . . ? C1 C2 C3 111.8(3) . . ? C1 C2 H2A 124.1 . . ? C3 C2 H2A 124.1 . . ? C4 C3 C2 113.2(3) . . ? C4 C3 H3A 123.4 . . ? C2 C3 H3A 123.4 . . ? C3 C4 C5 130.6(3) . . ? C3 C4 S1 111.2(2) . . ? C5 C4 S1 118.2(2) . . ? O1 C5 C4 120.2(3) . . ? O1 C5 C6 121.9(3) . . ? C4 C5 C6 117.8(3) . . ? C7 C6 C5 121.9(3) . . ? C7 C6 H6A 119.1 . . ? C5 C6 H6A 119.1 . . ? C6 C7 C8 127.7(4) . . ? C6 C7 H7A 116.1 . . ? C8 C7 H7A 116.1 . . ? C13 C8 C9 115.0(3) . . ? C13 C8 C7 122.0(4) . . ? C9 C8 C7 123.0(3) . . ? C10 C9 C8 121.6(4) . . ? C10 C9 H9A 119.2 . . ? C8 C9 H9A 119.2 . . ? C9 C10 C11 120.4(4) . . ? C9 C10 H10A 119.8 . . ? C11 C10 H10A 119.8 . . ? C12 C11 C10 120.2(4) . . ? C12 C11 H11A 119.9 . . ? C10 C11 H11A 119.9 . . ? C11 C12 C13 117.6(4) . . ? C11 C12 H12A 121.2 . . ? C13 C12 H12A 121.2 . . ? F1 C13 C8 117.9(4) . . ? F1 C13 C12 116.9(4) . . ? C8 C13 C12 125.2(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 C4 S1 C1 C2 -0.4(3) . . . . ? C4 S1 C1 Cl1 179.7(2) . . . . ? S1 C1 C2 C3 0.3(4) . . . . ? Cl1 C1 C2 C3 -179.8(3) . . . . ? C1 C2 C3 C4 0.1(5) . . . . ? C2 C3 C4 C5 178.9(3) . . . . ? C2 C3 C4 S1 -0.3(4) . . . . ? C1 S1 C4 C3 0.4(3) . . . . ? C1 S1 C4 C5 -178.9(3) . . . . ? C3 C4 C5 O1 -175.4(4) . . . . ? S1 C4 C5 O1 3.8(4) . . . . ? C3 C4 C5 C6 3.8(5) . . . . ? S1 C4 C5 C6 -177.0(2) . . . . ? O1 C5 C6 C7 -3.2(5) . . . . ? C4 C5 C6 C7 177.6(3) . . . . ? C5 C6 C7 C8 -178.8(3) . . . . ? C6 C7 C8 C13 174.6(4) . . . . ? C6 C7 C8 C9 -3.5(6) . . . . ? C13 C8 C9 C10 1.5(7) . . . . ? C7 C8 C9 C10 179.7(4) . . . . ? C8 C9 C10 C11 -2.0(8) . . . . ? C9 C10 C11 C12 2.3(8) . . . . ? C10 C11 C12 C13 -2.1(7) . . . . ? C9 C8 C13 F1 179.6(5) . . . . ? C7 C8 C13 F1 1.4(7) . . . . ? C9 C8 C13 C12 -1.4(7) . . . . ? C7 C8 C13 C12 -179.7(4) . . . . ? C11 C12 C13 F1 -179.3(5) . . . . ? C11 C12 C13 C8 1.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.94 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.197 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.052 #===================================================================== data_3b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H8 Cl F O S' _chemical_formula_sum 'C13 H8 Cl F O S' _chemical_formula_weight 266.70 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.282(6) _cell_length_b 7.698(4) _cell_length_c 11.376(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.430(8) _cell_angle_gamma 90.00 _cell_volume 1211.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 773 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 19.51 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.478 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.8890 _exptl_absorpt_correction_T_max 0.9751 _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 APEX Duo CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 9071 _diffrn_reflns_av_R_equivalents 0.0944 _diffrn_reflns_av_sigmaI/netI 0.0772 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2126 _reflns_number_gt 1133 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 2009) ; _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. ; _iucr_refine_instructions_details ; TITL mo_ch2_0m in P2(1)/c (RT) CELL 0.71073 14.2822 7.6982 11.3760 90.000 104.430 90.000 ZERR 4.00 0.0061 0.0035 0.0049 0.000 0.008 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H O F S CL UNIT 52 32 4 4 4 4 TEMP 24.000 SIZE 0.053 0.245 0.252 L.S. 10 BOND $H FMAP 2 2 60 PLAN 20 OMIT -4 50 OMIT 1 0 4 ACTA CONF WGHT 0.0994 0.0000 FVAR 0.60935 CL1 6 0.207031 0.533351 0.811823 11.00000 0.05414 0.08555 = 0.07650 -0.00139 0.00270 -0.00584 S1 5 0.405240 0.627134 0.796919 11.00000 0.06383 0.08396 = 0.04158 -0.00176 0.00768 -0.00861 F1 4 0.878723 1.028468 1.427407 11.00000 0.12766 0.20839 = 0.09446 -0.03802 0.00479 -0.02212 O1 3 0.607078 0.719661 0.811819 11.00000 0.07063 0.09910 = 0.05085 -0.00444 0.02105 -0.00861 C1 1 0.321132 0.611615 0.879250 11.00000 0.04987 0.05850 = 0.05684 0.00629 0.00669 0.00584 C2 1 0.353970 0.664995 0.996653 11.00000 0.06120 0.08179 = 0.05412 -0.00657 0.01832 -0.00158 AFIX 43 H2A 2 0.317390 0.664276 1.053800 11.00000 -1.20000 AFIX 0 C3 1 0.449745 0.720811 1.019569 11.00000 0.06186 0.06843 = 0.04803 -0.00656 0.00929 -0.00011 AFIX 43 H3A 2 0.484568 0.760565 1.095015 11.00000 -1.20000 AFIX 0 C4 1 0.487640 0.711459 0.920218 11.00000 0.05487 0.04618 = 0.04362 0.00118 0.00932 0.00230 C5 1 0.585573 0.749396 0.908064 11.00000 0.05510 0.05982 = 0.04605 0.00454 0.00788 0.00212 C6 1 0.654499 0.824733 1.013688 11.00000 0.05587 0.05708 = 0.05046 0.00348 0.01321 -0.00014 AFIX 43 H6A 2 0.637466 0.830905 1.087333 11.00000 -1.20000 AFIX 0 C7 1 0.739744 0.883855 1.007294 11.00000 0.06095 0.06931 = 0.05898 0.00724 0.01767 0.00340 AFIX 43 H7A 2 0.753768 0.876173 0.931898 11.00000 -1.20000 AFIX 0 C8 1 0.815067 0.960449 1.105647 11.00000 0.05487 0.05056 = 0.06876 0.00421 0.00828 0.00513 C9 1 0.810287 0.958067 1.226138 11.00000 0.05550 0.06791 = 0.07467 -0.00254 0.00831 -0.00155 AFIX 43 H9A 2 0.758399 0.906042 1.248162 11.00000 -1.20000 AFIX 0 C10 1 0.883437 1.033782 1.311778 11.00000 0.07428 0.09547 = 0.05777 -0.01626 0.00262 0.00469 C11 1 0.962039 1.113728 1.285400 11.00000 0.05439 0.07419 = 0.12432 -0.02639 -0.00207 0.00368 AFIX 43 H11A 2 1.009933 1.164904 1.346133 11.00000 -1.20000 AFIX 0 C12 1 0.967460 1.115468 1.165904 11.00000 0.05971 0.08381 = 0.12091 -0.00553 0.01718 0.00519 AFIX 43 H12A 2 1.019858 1.166552 1.144490 11.00000 -1.20000 AFIX 0 C13 1 0.894470 1.040798 1.079501 11.00000 0.05855 0.07711 = 0.08393 -0.00220 0.01713 -0.00461 AFIX 43 H13A 2 0.898283 1.044073 0.999104 11.00000 -1.20000 HKLF 4 1 0 0 1 0 -1 0 1 0 0 REM mo_ch2_0m in P2(1)/c (RT) REM R1 = 0.0589 for 1133 Fo > 4sig(Fo) and 0.1239 for all 2126 data REM 154 parameters refined using 0 restraints END WGHT 0.0994 0.0000 REM Highest difference peak 0.763, deepest hole -0.299, 1-sigma level 0.063 Q1 1 0.2812 0.5811 0.8608 11.00000 0.05 0.22 Q2 1 0.5348 0.7211 0.9171 11.00000 0.05 0.22 Q3 1 0.6775 0.7252 0.8575 11.00000 0.05 0.21 Q4 1 0.3599 0.6030 0.8254 11.00000 0.05 0.20 Q5 1 0.8024 1.0224 1.0945 11.00000 0.05 0.19 Q6 1 0.3231 0.6666 0.9447 11.00000 0.05 0.18 Q7 1 0.4649 0.6231 0.8989 11.00000 0.05 0.18 Q8 1 0.1232 0.5614 0.8032 11.00000 0.05 0.17 Q9 1 0.9631 1.0408 1.3219 11.00000 0.05 0.17 Q10 1 0.8613 1.0519 1.0248 11.00000 0.05 0.17 Q11 1 0.4681 0.6678 0.8632 11.00000 0.05 0.17 Q12 1 0.9854 1.2341 1.3672 11.00000 0.05 0.17 Q13 1 0.9651 1.1116 1.1928 11.00000 0.05 0.16 Q14 1 0.3567 0.8849 0.8182 11.00000 0.05 0.16 Q15 1 0.6225 0.7656 0.9536 11.00000 0.05 0.16 Q16 1 0.7578 0.9370 1.3819 11.00000 0.05 0.16 Q17 1 0.1579 0.3562 0.8459 11.00000 0.05 0.16 Q18 1 0.4865 0.6392 0.8166 11.00000 0.05 0.16 Q19 1 0.5715 0.8225 0.9225 11.00000 0.05 0.15 Q20 1 0.2675 0.6522 0.7636 11.00000 0.05 0.15 ; _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^)+(0.0994P)^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_number_reflns 2126 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1239 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1912 _refine_ls_wR_factor_gt 0.1530 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 Cl1 Cl 0.20703(9) 0.5334(2) 0.81182(12) 0.0745(5) Uani 1 1 d . . . S1 S 0.40524(9) 0.6271(2) 0.79692(10) 0.0641(5) Uani 1 1 d . . . F1 F 0.8787(3) 1.0285(8) 1.4274(4) 0.1476(18) Uani 1 1 d . . . O1 O 0.6071(2) 0.7197(5) 0.8118(3) 0.0725(11) Uani 1 1 d . . . C1 C 0.3211(3) 0.6116(7) 0.8792(4) 0.0562(13) Uani 1 1 d . . . C2 C 0.3540(3) 0.6650(8) 0.9967(4) 0.0650(15) Uani 1 1 d . . . H2A H 0.3174 0.6643 1.0538 0.078 Uiso 1 1 calc R . . C3 C 0.4497(3) 0.7208(7) 1.0196(4) 0.0602(13) Uani 1 1 d . . . H3A H 0.4846 0.7606 1.0950 0.072 Uiso 1 1 calc R . . C4 C 0.4876(3) 0.7115(6) 0.9202(4) 0.0487(12) Uani 1 1 d . . . C5 C 0.5856(3) 0.7494(7) 0.9081(4) 0.0545(13) Uani 1 1 d . . . C6 C 0.6545(3) 0.8247(6) 1.0137(4) 0.0545(13) Uani 1 1 d . . . H6A H 0.6375 0.8309 1.0873 0.065 Uiso 1 1 calc R . . C7 C 0.7397(3) 0.8839(7) 1.0073(4) 0.0626(14) Uani 1 1 d . . . H7A H 0.7538 0.8762 0.9319 0.075 Uiso 1 1 calc R . . C8 C 0.8151(3) 0.9604(7) 1.1056(5) 0.0593(13) Uani 1 1 d . . . C9 C 0.8103(3) 0.9581(8) 1.2261(5) 0.0674(15) Uani 1 1 d . . . H9A H 0.7584 0.9060 1.2482 0.081 Uiso 1 1 calc R . . C10 C 0.8834(4) 1.0338(9) 1.3118(5) 0.0783(17) Uani 1 1 d . . . C11 C 0.9620(4) 1.1137(8) 1.2854(7) 0.089(2) Uani 1 1 d . . . H11A H 1.0099 1.1649 1.3461 0.106 Uiso 1 1 calc R . . C12 C 0.9675(4) 1.1155(9) 1.1659(7) 0.0891(19) Uani 1 1 d . . . H12A H 1.0199 1.1666 1.1445 0.107 Uiso 1 1 calc R . . C13 C 0.8945(4) 1.0408(8) 1.0795(6) 0.0733(16) Uani 1 1 d . . . H13A H 0.8983 1.0441 0.9991 0.088 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 Cl1 0.0541(7) 0.0856(12) 0.0765(9) -0.0014(8) 0.0027(6) -0.0058(7) S1 0.0638(8) 0.0840(11) 0.0416(7) -0.0018(7) 0.0077(5) -0.0086(7) F1 0.128(3) 0.208(5) 0.094(3) -0.038(3) 0.005(2) -0.022(3) O1 0.071(2) 0.099(3) 0.051(2) -0.004(2) 0.0210(17) -0.009(2) C1 0.050(3) 0.059(3) 0.057(3) 0.006(3) 0.007(2) 0.006(2) C2 0.061(3) 0.082(4) 0.054(3) -0.007(3) 0.018(2) -0.002(3) C3 0.062(3) 0.068(4) 0.048(3) -0.007(3) 0.009(2) 0.000(3) C4 0.055(3) 0.046(3) 0.044(2) 0.001(2) 0.009(2) 0.002(2) C5 0.055(3) 0.060(4) 0.046(2) 0.005(3) 0.008(2) 0.002(3) C6 0.056(3) 0.057(4) 0.050(3) 0.003(2) 0.013(2) 0.000(2) C7 0.061(3) 0.069(4) 0.059(3) 0.007(3) 0.018(2) 0.003(3) C8 0.055(3) 0.051(3) 0.069(3) 0.004(3) 0.008(2) 0.005(3) C9 0.055(3) 0.068(4) 0.075(3) -0.003(3) 0.008(3) -0.002(3) C10 0.074(4) 0.095(5) 0.058(3) -0.016(3) 0.003(3) 0.005(3) C11 0.054(3) 0.074(4) 0.124(6) -0.026(4) -0.002(3) 0.004(3) C12 0.060(4) 0.084(5) 0.121(6) -0.006(4) 0.017(4) 0.005(3) C13 0.059(3) 0.077(4) 0.084(4) -0.002(3) 0.017(3) -0.005(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 Cl1 C1 1.727(5) . ? S1 C1 1.702(5) . ? S1 C4 1.718(4) . ? F1 C10 1.334(7) . ? O1 C5 1.230(5) . ? C1 C2 1.364(6) . ? C2 C3 1.395(6) . ? C2 H2A 0.9300 . ? C3 C4 1.371(6) . ? C3 H3A 0.9300 . ? C4 C5 1.469(6) . ? C5 C6 1.470(6) . ? C6 C7 1.319(6) . ? C6 H6A 0.9300 . ? C7 C8 1.469(7) . ? C7 H7A 0.9300 . ? C8 C13 1.388(7) . ? C8 C9 1.389(7) . ? C9 C10 1.369(7) . ? C9 H9A 0.9300 . ? C10 C11 1.377(8) . ? C11 C12 1.381(9) . ? C11 H11A 0.9300 . ? C12 C13 1.368(8) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? 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 S1 C4 90.6(2) . . ? C2 C1 S1 113.6(4) . . ? C2 C1 Cl1 126.6(4) . . ? S1 C1 Cl1 119.8(3) . . ? C1 C2 C3 111.0(4) . . ? C1 C2 H2A 124.5 . . ? C3 C2 H2A 124.5 . . ? C4 C3 C2 113.6(4) . . ? C4 C3 H3A 123.2 . . ? C2 C3 H3A 123.2 . . ? C3 C4 C5 130.4(4) . . ? C3 C4 S1 111.2(3) . . ? C5 C4 S1 118.2(3) . . ? O1 C5 C4 120.1(4) . . ? O1 C5 C6 122.4(4) . . ? C4 C5 C6 117.5(4) . . ? C7 C6 C5 122.1(4) . . ? C7 C6 H6A 119.0 . . ? C5 C6 H6A 119.0 . . ? C6 C7 C8 127.4(5) . . ? C6 C7 H7A 116.3 . . ? C8 C7 H7A 116.3 . . ? C13 C8 C9 117.5(5) . . ? C13 C8 C7 119.9(5) . . ? C9 C8 C7 122.7(5) . . ? C10 C9 C8 118.7(5) . . ? C10 C9 H9A 120.7 . . ? C8 C9 H9A 120.7 . . ? F1 C10 C9 118.1(6) . . ? F1 C10 C11 118.2(6) . . ? C9 C10 C11 123.7(6) . . ? C10 C11 C12 117.9(6) . . ? C10 C11 H11A 121.1 . . ? C12 C11 H11A 121.1 . . ? C13 C12 C11 118.9(6) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? C12 C13 C8 123.4(6) . . ? C12 C13 H13A 118.3 . . ? C8 C13 H13A 118.3 . . ? 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 C4 S1 C1 C2 -1.1(5) . . . . ? C4 S1 C1 Cl1 179.1(3) . . . . ? S1 C1 C2 C3 0.4(6) . . . . ? Cl1 C1 C2 C3 -179.8(4) . . . . ? C1 C2 C3 C4 0.8(7) . . . . ? C2 C3 C4 C5 -176.8(5) . . . . ? C2 C3 C4 S1 -1.6(6) . . . . ? C1 S1 C4 C3 1.5(4) . . . . ? C1 S1 C4 C5 177.3(4) . . . . ? C3 C4 C5 O1 174.4(5) . . . . ? S1 C4 C5 O1 -0.5(7) . . . . ? C3 C4 C5 C6 -6.3(8) . . . . ? S1 C4 C5 C6 178.8(4) . . . . ? O1 C5 C6 C7 8.1(8) . . . . ? C4 C5 C6 C7 -171.1(5) . . . . ? C5 C6 C7 C8 -179.5(5) . . . . ? C6 C7 C8 C13 -170.0(5) . . . . ? C6 C7 C8 C9 9.3(9) . . . . ? C13 C8 C9 C10 -0.2(8) . . . . ? C7 C8 C9 C10 -179.5(5) . . . . ? C8 C9 C10 F1 -179.1(6) . . . . ? C8 C9 C10 C11 0.3(9) . . . . ? F1 C10 C11 C12 178.6(6) . . . . ? C9 C10 C11 C12 -0.7(10) . . . . ? C10 C11 C12 C13 1.0(9) . . . . ? C11 C12 C13 C8 -0.9(9) . . . . ? C9 C8 C13 C12 0.5(9) . . . . ? C7 C8 C13 C12 179.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.763 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.063 #============================================================== data_3c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H8 Cl F O S' _chemical_formula_sum 'C13 H8 Cl F O S' _chemical_formula_weight 266.70 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' '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_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' 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' '-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 7.9809(8) _cell_length_b 11.0207(11) _cell_length_c 27.518(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2420.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4322 _cell_measurement_theta_min 3.24 _cell_measurement_theta_max 25.27 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.79 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.479 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.7038 _exptl_absorpt_correction_T_max 0.9802 _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 APEX Duo CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 24679 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 30.05 _reflns_number_total 3540 _reflns_number_gt 2016 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 2009) ; _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. ; _iucr_refine_instructions_details ; TITL mo_ch3_0m in Pbca (RT) CELL 0.71073 7.9809 11.0207 27.5178 90.000 90.000 90.000 ZERR 8.00 0.0008 0.0011 0.0025 0.000 0.000 0.000 LATT 1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H O F S CL UNIT 104 64 8 8 8 8 TEMP 24.000 SIZE 0.042 0.369 0.789 L.S. 10 BOND $H FMAP 2 1 60 PLAN 20 ACTA CONF WGHT 0.0459 1.0741 FVAR 0.41108 CL1 6 0.009493 0.579609 0.350258 11.00000 0.07771 0.09376 = 0.05862 0.01303 -0.00504 -0.00686 S1 5 0.099891 0.667111 0.448427 11.00000 0.07290 0.04724 = 0.06719 0.00552 -0.00398 0.00304 F1 4 0.703145 0.300322 0.755843 11.00000 0.10900 0.14471 = 0.07472 0.02098 -0.02796 0.00738 O1 3 0.200130 0.725320 0.548512 11.00000 0.09268 0.04802 = 0.07205 -0.00682 0.00181 0.00247 C1 1 0.096699 0.554447 0.406238 11.00000 0.05038 0.06334 = 0.05409 0.00605 0.00232 -0.00504 C2 1 0.166270 0.450421 0.422071 11.00000 0.08641 0.05580 = 0.06296 -0.00844 -0.00211 0.00896 AFIX 43 H2A 2 0.174399 0.379970 0.403617 11.00000 -1.20000 AFIX 0 C3 1 0.224959 0.461681 0.469915 11.00000 0.07095 0.04942 = 0.05937 -0.00156 -0.00507 0.01008 AFIX 43 H3A 2 0.276233 0.398657 0.486766 11.00000 -1.20000 AFIX 0 C4 1 0.199532 0.573877 0.489274 11.00000 0.04533 0.04290 = 0.05829 0.00339 0.00752 -0.00214 C5 1 0.237988 0.620026 0.537638 11.00000 0.05213 0.04587 = 0.05969 -0.00238 0.00795 -0.00545 C6 1 0.322240 0.538339 0.571765 11.00000 0.05984 0.04717 = 0.05692 -0.00089 0.00304 -0.00354 AFIX 43 H6A 2 0.339113 0.458019 0.562628 11.00000 -1.20000 AFIX 0 C7 1 0.375637 0.573991 0.615224 11.00000 0.06416 0.05431 = 0.05985 -0.00285 0.00355 -0.01122 AFIX 43 H7A 2 0.357082 0.654855 0.623250 11.00000 -1.20000 AFIX 0 C8 1 0.460184 0.500019 0.651690 11.00000 0.05405 0.06287 = 0.05142 -0.00379 0.00392 -0.01019 C9 1 0.472167 0.374311 0.647910 11.00000 0.06897 0.06913 = 0.05772 -0.00586 -0.00525 -0.00586 AFIX 43 H9A 2 0.424664 0.335384 0.621276 11.00000 -1.20000 AFIX 0 C10 1 0.552714 0.306634 0.682714 11.00000 0.07751 0.07496 = 0.06525 0.00492 -0.00167 0.00021 AFIX 43 H10A 2 0.559685 0.222658 0.680065 11.00000 -1.20000 AFIX 0 C11 1 0.622482 0.366214 0.721425 11.00000 0.06423 0.10312 = 0.05608 0.00931 -0.00341 -0.00236 C12 1 0.615575 0.488516 0.726956 11.00000 0.07964 0.11101 = 0.05425 -0.00865 -0.00537 -0.02078 AFIX 43 H12A 2 0.665350 0.526507 0.753457 11.00000 -1.20000 AFIX 0 C13 1 0.532103 0.554488 0.691875 11.00000 0.07742 0.07584 = 0.05433 -0.01089 -0.00013 -0.01490 AFIX 43 H13A 2 0.523956 0.638216 0.695365 11.00000 -1.20000 HKLF 4 1 0 -1 0 1 0 0 0 0 1 REM mo_ch3_0m in Pbca (RT) REM R1 = 0.0465 for 2016 Fo > 4sig(Fo) and 0.0961 for all 3540 data REM 154 parameters refined using 0 restraints END WGHT 0.0459 1.0741 REM Highest difference peak 0.188, deepest hole -0.269, 1-sigma level 0.041 Q1 1 0.0310 0.4802 0.3407 11.00000 0.05 0.19 Q2 1 0.1064 0.5827 0.4821 11.00000 0.05 0.17 Q3 1 0.1935 0.5154 0.4821 11.00000 0.05 0.15 Q4 1 0.5201 0.5925 0.6960 11.00000 0.05 0.14 Q5 1 0.2799 0.5807 0.4958 11.00000 0.05 0.14 Q6 1 0.3109 0.5848 0.5612 11.00000 0.05 0.14 Q7 1 0.2121 0.6643 0.4473 11.00000 0.05 0.14 Q8 1 0.6131 0.6524 0.6840 11.00000 0.05 0.13 Q9 1 0.5098 0.5015 0.7192 11.00000 0.05 0.13 Q10 1 0.0391 0.3472 0.4345 11.00000 0.05 0.13 Q11 1 0.4368 0.4533 0.6605 11.00000 0.05 0.13 Q12 1 0.4267 0.6930 0.6177 11.00000 0.05 0.13 Q13 1 0.7168 0.3907 0.7621 11.00000 0.05 0.13 Q14 1 0.0602 0.5460 0.5190 11.00000 0.05 0.13 Q15 1 0.5823 0.5661 0.6806 11.00000 0.05 0.13 Q16 1 0.7462 0.2934 0.6420 11.00000 0.05 0.12 Q17 1 0.1964 0.8408 0.5564 11.00000 0.05 0.12 Q18 1 0.3978 0.5562 0.5792 11.00000 0.05 0.12 Q19 1 0.5367 0.5155 0.6589 11.00000 0.05 0.12 Q20 1 0.5605 0.3471 0.7029 11.00000 0.05 0.12 ; _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^)+(0.0459P)^2^+1.0741P] 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_number_reflns 3540 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1353 _refine_ls_wR_factor_gt 0.1119 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 Cl1 Cl 0.00949(10) 0.57961(7) 0.35026(2) 0.0767(2) Uani 1 1 d . . . S1 S 0.09989(9) 0.66711(5) 0.44843(2) 0.0624(2) Uani 1 1 d . . . F1 F 0.7031(3) 0.30032(19) 0.75584(6) 0.1095(7) Uani 1 1 d . . . O1 O 0.2001(3) 0.72532(14) 0.54851(6) 0.0709(5) Uani 1 1 d . . . C1 C 0.0967(3) 0.5544(2) 0.40624(8) 0.0559(6) Uani 1 1 d . . . C2 C 0.1663(4) 0.4504(2) 0.42207(9) 0.0684(7) Uani 1 1 d . . . H2A H 0.1744 0.3800 0.4036 0.082 Uiso 1 1 calc R . . C3 C 0.2250(3) 0.4617(2) 0.46992(8) 0.0599(6) Uani 1 1 d . . . H3A H 0.2762 0.3987 0.4868 0.072 Uiso 1 1 calc R . . C4 C 0.1995(3) 0.57388(17) 0.48927(8) 0.0488(5) Uani 1 1 d . . . C5 C 0.2380(3) 0.62003(19) 0.53764(8) 0.0526(5) Uani 1 1 d . . . C6 C 0.3222(3) 0.5383(2) 0.57176(8) 0.0546(6) Uani 1 1 d . . . H6A H 0.3391 0.4580 0.5626 0.066 Uiso 1 1 calc R . . C7 C 0.3756(3) 0.5740(2) 0.61522(8) 0.0594(6) Uani 1 1 d . . . H7A H 0.3571 0.6549 0.6232 0.071 Uiso 1 1 calc R . . C8 C 0.4602(3) 0.5000(2) 0.65169(8) 0.0561(6) Uani 1 1 d . . . C9 C 0.4722(3) 0.3743(2) 0.64791(9) 0.0653(7) Uani 1 1 d . . . H9A H 0.4247 0.3354 0.6213 0.078 Uiso 1 1 calc R . . C10 C 0.5527(4) 0.3066(3) 0.68271(9) 0.0726(7) Uani 1 1 d . . . H10A H 0.5597 0.2227 0.6801 0.087 Uiso 1 1 calc R . . C11 C 0.6225(4) 0.3662(3) 0.72143(9) 0.0745(8) Uani 1 1 d . . . C12 C 0.6156(4) 0.4885(3) 0.72696(10) 0.0816(8) Uani 1 1 d . . . H12A H 0.6654 0.5265 0.7535 0.098 Uiso 1 1 calc R . . C13 C 0.5321(4) 0.5545(2) 0.69187(9) 0.0692(7) Uani 1 1 d . . . H13A H 0.5240 0.6382 0.6954 0.083 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 Cl1 0.0777(5) 0.0938(5) 0.0586(4) 0.0130(3) -0.0050(3) -0.0069(4) S1 0.0729(5) 0.0472(3) 0.0672(4) 0.0055(3) -0.0040(3) 0.0030(3) F1 0.1090(15) 0.1447(16) 0.0747(11) 0.0210(11) -0.0280(10) 0.0074(13) O1 0.0927(14) 0.0480(9) 0.0721(11) -0.0068(8) 0.0018(10) 0.0025(9) C1 0.0504(14) 0.0633(13) 0.0541(12) 0.0061(10) 0.0023(11) -0.0050(11) C2 0.086(2) 0.0558(13) 0.0630(15) -0.0084(11) -0.0021(14) 0.0090(13) C3 0.0710(17) 0.0494(11) 0.0594(13) -0.0016(10) -0.0051(13) 0.0101(12) C4 0.0453(13) 0.0429(10) 0.0583(12) 0.0034(9) 0.0075(10) -0.0021(9) C5 0.0521(13) 0.0459(10) 0.0597(12) -0.0024(9) 0.0080(11) -0.0055(10) C6 0.0598(15) 0.0472(11) 0.0569(13) -0.0009(10) 0.0030(11) -0.0035(10) C7 0.0642(16) 0.0543(12) 0.0598(13) -0.0029(10) 0.0035(12) -0.0112(11) C8 0.0540(15) 0.0629(13) 0.0514(12) -0.0038(10) 0.0039(11) -0.0102(11) C9 0.0690(17) 0.0691(15) 0.0577(14) -0.0059(11) -0.0052(13) -0.0059(13) C10 0.0775(19) 0.0750(16) 0.0652(16) 0.0049(13) -0.0017(15) 0.0002(14) C11 0.0642(18) 0.103(2) 0.0561(15) 0.0093(14) -0.0034(13) -0.0024(16) C12 0.080(2) 0.111(2) 0.0543(15) -0.0087(15) -0.0054(14) -0.0208(18) C13 0.0774(19) 0.0758(16) 0.0543(14) -0.0109(12) -0.0001(13) -0.0149(14) _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 Cl1 C1 1.713(2) . ? S1 C1 1.700(2) . ? S1 C4 1.718(2) . ? F1 C11 1.356(3) . ? O1 C5 1.236(3) . ? C1 C2 1.346(3) . ? C2 C3 1.403(3) . ? C2 H2A 0.9300 . ? C3 C4 1.362(3) . ? C3 H3A 0.9300 . ? C4 C5 1.457(3) . ? C5 C6 1.464(3) . ? C6 C7 1.329(3) . ? C6 H6A 0.9300 . ? C7 C8 1.458(3) . ? C7 H7A 0.9300 . ? C8 C13 1.383(3) . ? C8 C9 1.393(4) . ? C9 C10 1.374(4) . ? C9 H9A 0.9300 . ? C10 C11 1.370(4) . ? C10 H10A 0.9300 . ? C11 C12 1.358(4) . ? C12 C13 1.380(4) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? 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 S1 C4 90.97(11) . . ? C2 C1 S1 113.25(19) . . ? C2 C1 Cl1 126.62(19) . . ? S1 C1 Cl1 120.13(14) . . ? C1 C2 C3 111.5(2) . . ? C1 C2 H2A 124.3 . . ? C3 C2 H2A 124.3 . . ? C4 C3 C2 113.4(2) . . ? C4 C3 H3A 123.3 . . ? C2 C3 H3A 123.3 . . ? C3 C4 C5 130.0(2) . . ? C3 C4 S1 110.86(17) . . ? C5 C4 S1 119.09(15) . . ? O1 C5 C4 119.8(2) . . ? O1 C5 C6 122.3(2) . . ? C4 C5 C6 117.89(19) . . ? C7 C6 C5 122.9(2) . . ? C7 C6 H6A 118.6 . . ? C5 C6 H6A 118.6 . . ? C6 C7 C8 127.0(2) . . ? C6 C7 H7A 116.5 . . ? C8 C7 H7A 116.5 . . ? C13 C8 C9 117.6(2) . . ? C13 C8 C7 120.0(2) . . ? C9 C8 C7 122.4(2) . . ? C10 C9 C8 121.3(2) . . ? C10 C9 H9A 119.3 . . ? C8 C9 H9A 119.3 . . ? C11 C10 C9 118.2(3) . . ? C11 C10 H10A 120.9 . . ? C9 C10 H10A 120.9 . . ? F1 C11 C12 118.2(3) . . ? F1 C11 C10 118.7(3) . . ? C12 C11 C10 123.1(3) . . ? C11 C12 C13 117.7(3) . . ? C11 C12 H12A 121.2 . . ? C13 C12 H12A 121.2 . . ? C12 C13 C8 122.1(3) . . ? C12 C13 H13A 119.0 . . ? C8 C13 H13A 119.0 . . ? 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 C4 S1 C1 C2 0.5(2) . . . . ? C4 S1 C1 Cl1 -179.90(16) . . . . ? S1 C1 C2 C3 -0.2(3) . . . . ? Cl1 C1 C2 C3 -179.8(2) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C2 C3 C4 C5 178.2(2) . . . . ? C2 C3 C4 S1 0.6(3) . . . . ? C1 S1 C4 C3 -0.63(19) . . . . ? C1 S1 C4 C5 -178.47(19) . . . . ? C3 C4 C5 O1 -178.0(2) . . . . ? S1 C4 C5 O1 -0.6(3) . . . . ? C3 C4 C5 C6 2.4(4) . . . . ? S1 C4 C5 C6 179.71(17) . . . . ? O1 C5 C6 C7 -5.4(4) . . . . ? C4 C5 C6 C7 174.2(2) . . . . ? C5 C6 C7 C8 179.9(2) . . . . ? C6 C7 C8 C13 169.5(3) . . . . ? C6 C7 C8 C9 -10.5(4) . . . . ? C13 C8 C9 C10 -0.1(4) . . . . ? C7 C8 C9 C10 179.9(2) . . . . ? C8 C9 C10 C11 -0.4(4) . . . . ? C9 C10 C11 F1 -179.6(2) . . . . ? C9 C10 C11 C12 0.1(5) . . . . ? F1 C11 C12 C13 -179.5(3) . . . . ? C10 C11 C12 C13 0.8(5) . . . . ? C11 C12 C13 C8 -1.3(4) . . . . ? C9 C8 C13 C12 1.0(4) . . . . ? C7 C8 C13 C12 -179.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.05 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.188 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.041 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C3 H3A O1 0.9300 2.5600 3.438(3) 157.00 8_655 yes C9 H9A O1 0.9300 2.5400 3.474(3) 179.00 8_655 yes #============================================================= data_3d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H7 Cl2 F O S' _chemical_formula_sum 'C13 H7 Cl2 F O S' _chemical_formula_weight 301.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 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' 'F' 'F' 0.0171 0.0103 '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_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' 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' '-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 7.4870(9) _cell_length_b 11.6186(14) _cell_length_c 29.239(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2543.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3573 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 26.43 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.669 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.6333 _exptl_absorpt_correction_T_max 0.9349 _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 APEX Duo CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 16026 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 30.11 _reflns_number_total 3738 _reflns_number_gt 2486 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 2009) ; _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. ; _iucr_refine_instructions_details ; TITL mo_ch12_0m in Pbca (RT) CELL 0.71073 7.4870 11.6186 29.2388 90.000 90.000 90.000 ZERR 8.00 0.0009 0.0014 0.0036 0.000 0.000 0.000 LATT 1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H O S F CL UNIT 104 56 8 8 8 16 TEMP 24.000 SIZE 0.102 0.518 0.752 L.S. 10 BOND $H FMAP 2 1 60 PLAN 20 ACTA CONF WGHT 0.071900 0.117800 FVAR 0.37522 CL1 6 0.043204 0.896427 0.359476 11.00000 0.06987 0.06547 = 0.05832 -0.01179 -0.00522 0.00302 CL2 6 0.565991 1.307997 0.674832 11.00000 0.10688 0.05566 = 0.07527 -0.00807 -0.01071 -0.01078 S1 4 0.111852 0.815633 0.454024 11.00000 0.06765 0.03672 = 0.06683 -0.00547 -0.00828 -0.00466 F1 5 0.652652 1.172332 0.755693 11.00000 0.11730 0.09994 = 0.06185 -0.01658 -0.02744 0.01068 O1 3 0.181315 0.764038 0.550750 11.00000 0.07864 0.04308 = 0.07318 0.00631 -0.00467 -0.00920 C1 1 0.121056 0.921923 0.413704 11.00000 0.04655 0.04601 = 0.05813 -0.00769 0.00224 0.00205 C2 1 0.190101 1.021976 0.429904 11.00000 0.06636 0.04761 = 0.05818 0.00291 -0.00076 -0.00859 AFIX 43 H2A 2 0.204480 1.088378 0.412529 11.00000 -1.20000 AFIX 0 C3 1 0.237157 1.012384 0.476365 11.00000 0.05895 0.04113 = 0.05990 -0.00301 -0.00229 -0.00821 AFIX 43 H3A 2 0.286269 1.072538 0.493163 11.00000 -1.20000 AFIX 0 C4 1 0.203627 0.906137 0.494339 11.00000 0.04187 0.03682 = 0.05793 -0.00463 0.00082 0.00033 C5 1 0.225878 0.863388 0.540998 11.00000 0.04406 0.04026 = 0.06217 0.00014 0.00224 0.00293 C6 1 0.304483 0.942797 0.574538 11.00000 0.05094 0.03943 = 0.05997 0.00144 0.00163 0.00093 AFIX 43 H6A 2 0.325761 1.018650 0.565966 11.00000 -1.20000 AFIX 0 C7 1 0.346014 0.909861 0.616579 11.00000 0.05305 0.04147 = 0.05845 0.00462 0.00254 0.00197 AFIX 43 H7A 2 0.321879 0.833596 0.624001 11.00000 -1.20000 AFIX 0 C8 1 0.425784 0.980561 0.652603 11.00000 0.04977 0.04912 = 0.04866 0.00427 0.00633 0.00688 C9 1 0.453249 1.098877 0.647053 11.00000 0.05160 0.04944 = 0.04367 0.00287 -0.00183 0.00373 AFIX 43 H9A 2 0.419986 1.134528 0.619878 11.00000 -1.20000 AFIX 0 C10 1 0.529150 1.162715 0.681558 11.00000 0.05357 0.05224 = 0.05145 -0.00132 0.00265 0.00555 C11 1 0.577985 1.109309 0.722023 11.00000 0.06715 0.07709 = 0.04283 -0.00800 -0.00522 0.01062 C12 1 0.552707 0.993707 0.728210 11.00000 0.09302 0.07914 = 0.04534 0.01430 -0.00557 0.01389 AFIX 43 H12A 2 0.587122 0.958729 0.755428 11.00000 -1.20000 AFIX 0 C13 1 0.476130 0.929717 0.693922 11.00000 0.07990 0.05772 = 0.05662 0.01499 0.00322 0.00940 AFIX 43 H13A 2 0.457522 0.851342 0.698286 11.00000 -1.20000 HKLF 4 REM mo_ch12_0m in Pbca (RT) REM R1 = 0.0411 for 2486 Fo > 4sig(Fo) and 0.0677 for all 3738 data REM 163 parameters refined using 0 restraints END WGHT 0.0719 0.1178 REM Highest difference peak 0.197, deepest hole -0.269, 1-sigma level 0.054 Q1 1 0.1096 0.8368 0.3634 11.00000 0.05 0.20 Q2 1 0.5460 1.1884 0.7594 11.00000 0.05 0.16 Q3 1 0.4540 1.2738 0.6821 11.00000 0.05 0.16 Q4 1 -0.0412 0.7032 0.5027 11.00000 0.05 0.16 Q5 1 0.6154 1.0437 0.7189 11.00000 0.05 0.15 Q6 1 0.8058 1.1880 0.7219 11.00000 0.05 0.15 Q7 1 0.1097 1.1641 0.5163 11.00000 0.05 0.15 Q8 1 0.5509 0.8307 0.6963 11.00000 0.05 0.14 Q9 1 0.3987 1.0648 0.7229 11.00000 0.05 0.14 Q10 1 0.2100 0.9556 0.4165 11.00000 0.05 0.14 Q11 1 0.2591 0.9402 0.4832 11.00000 0.05 0.14 Q12 1 0.8391 1.1121 0.7250 11.00000 0.05 0.14 Q13 1 0.1019 0.9758 0.4172 11.00000 0.05 0.14 Q14 1 0.1049 0.7988 0.5429 11.00000 0.05 0.14 Q15 1 0.6957 0.8378 0.7001 11.00000 0.05 0.14 Q16 1 0.5960 1.1211 0.6966 11.00000 0.05 0.14 Q17 1 0.0598 1.1389 0.4030 11.00000 0.05 0.14 Q18 1 0.6431 1.2666 0.6830 11.00000 0.05 0.14 Q19 1 0.3064 1.1335 0.6171 11.00000 0.05 0.14 Q20 1 0.3869 0.9528 0.6055 11.00000 0.05 0.13 ; _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^)+(0.0719P)^2^+0.1178P] 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_number_reflns 3738 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1159 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _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 Cl1 Cl 0.04320(7) 0.89643(5) 0.359476(17) 0.06456(18) Uani 1 1 d . . . Cl2 Cl 0.56599(10) 1.30800(5) 0.67483(2) 0.0793(2) Uani 1 1 d . . . S1 S 0.11185(7) 0.81563(4) 0.454024(18) 0.05707(17) Uani 1 1 d . . . F1 F 0.6527(2) 1.17233(14) 0.75569(5) 0.0930(5) Uani 1 1 d . . . O1 O 0.1813(2) 0.76404(11) 0.55075(5) 0.0650(4) Uani 1 1 d . . . C1 C 0.1211(2) 0.92192(16) 0.41370(7) 0.0502(4) Uani 1 1 d . . . C2 C 0.1901(3) 1.02198(16) 0.42990(7) 0.0574(5) Uani 1 1 d . . . H2A H 0.2045 1.0884 0.4125 0.069 Uiso 1 1 calc R . . C3 C 0.2372(3) 1.01238(15) 0.47637(7) 0.0533(4) Uani 1 1 d . . . H3A H 0.2863 1.0725 0.4932 0.064 Uiso 1 1 calc R . . C4 C 0.2036(2) 0.90614(14) 0.49434(6) 0.0455(4) Uani 1 1 d . . . C5 C 0.2259(2) 0.86339(16) 0.54100(6) 0.0488(4) Uani 1 1 d . . . C6 C 0.3045(2) 0.94280(15) 0.57454(6) 0.0501(4) Uani 1 1 d . . . H6A H 0.3258 1.0187 0.5660 0.060 Uiso 1 1 calc R . . C7 C 0.3460(2) 0.90986(16) 0.61658(6) 0.0510(4) Uani 1 1 d . . . H7A H 0.3219 0.8336 0.6240 0.061 Uiso 1 1 calc R . . C8 C 0.4258(2) 0.98056(16) 0.65260(6) 0.0492(4) Uani 1 1 d . . . C9 C 0.4532(2) 1.09888(15) 0.64705(6) 0.0482(4) Uani 1 1 d . . . H9A H 0.4200 1.1345 0.6199 0.058 Uiso 1 1 calc R . . C10 C 0.5292(3) 1.16272(17) 0.68156(6) 0.0524(4) Uani 1 1 d . . . C11 C 0.5780(3) 1.1093(2) 0.72202(7) 0.0624(5) Uani 1 1 d . . . C12 C 0.5527(3) 0.9937(2) 0.72821(7) 0.0725(6) Uani 1 1 d . . . H12A H 0.5871 0.9587 0.7554 0.087 Uiso 1 1 calc R . . C13 C 0.4761(3) 0.9297(2) 0.69392(7) 0.0647(5) Uani 1 1 d . . . H13A H 0.4575 0.8513 0.6983 0.078 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 Cl1 0.0699(3) 0.0655(3) 0.0583(3) -0.0118(2) -0.0052(2) 0.0030(2) Cl2 0.1069(5) 0.0557(3) 0.0753(4) -0.0081(3) -0.0107(3) -0.0108(3) S1 0.0676(3) 0.0367(3) 0.0668(3) -0.0055(2) -0.0083(2) -0.0047(2) F1 0.1173(12) 0.0999(11) 0.0618(8) -0.0166(7) -0.0274(8) 0.0107(9) O1 0.0786(10) 0.0431(8) 0.0732(9) 0.0063(6) -0.0047(7) -0.0092(7) C1 0.0465(9) 0.0460(10) 0.0581(10) -0.0077(8) 0.0022(7) 0.0020(8) C2 0.0664(12) 0.0476(11) 0.0582(11) 0.0029(8) -0.0008(9) -0.0086(9) C3 0.0589(11) 0.0411(9) 0.0599(10) -0.0030(8) -0.0023(8) -0.0082(8) C4 0.0419(8) 0.0368(8) 0.0579(10) -0.0046(7) 0.0008(7) 0.0003(7) C5 0.0441(9) 0.0403(9) 0.0622(10) 0.0001(8) 0.0022(7) 0.0029(8) C6 0.0509(10) 0.0394(9) 0.0600(10) 0.0014(8) 0.0016(8) 0.0009(8) C7 0.0531(10) 0.0415(10) 0.0584(10) 0.0046(8) 0.0025(8) 0.0020(8) C8 0.0498(10) 0.0491(10) 0.0487(9) 0.0043(8) 0.0063(7) 0.0069(8) C9 0.0516(10) 0.0494(10) 0.0437(8) 0.0029(7) -0.0018(7) 0.0037(8) C10 0.0536(10) 0.0522(11) 0.0514(10) -0.0013(8) 0.0026(8) 0.0055(8) C11 0.0671(12) 0.0771(15) 0.0428(9) -0.0080(9) -0.0052(8) 0.0106(11) C12 0.0930(17) 0.0791(15) 0.0453(10) 0.0143(10) -0.0056(10) 0.0139(13) C13 0.0799(14) 0.0577(12) 0.0566(11) 0.0150(10) 0.0032(10) 0.0094(10) _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 Cl1 C1 1.715(2) . ? Cl2 C10 1.722(2) . ? S1 C1 1.709(2) . ? S1 C4 1.7226(17) . ? F1 C11 1.348(2) . ? O1 C5 1.235(2) . ? C1 C2 1.358(3) . ? C2 C3 1.408(3) . ? C2 H2A 0.9300 . ? C3 C4 1.365(2) . ? C3 H3A 0.9300 . ? C4 C5 1.461(3) . ? C5 C6 1.469(3) . ? C6 C7 1.324(3) . ? C6 H6A 0.9300 . ? C7 C8 1.463(3) . ? C7 H7A 0.9300 . ? C8 C13 1.397(3) . ? C8 C9 1.399(3) . ? C9 C10 1.375(3) . ? C9 H9A 0.9300 . ? C10 C11 1.385(3) . ? C11 C12 1.368(3) . ? C12 C13 1.374(3) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? 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 S1 C4 90.85(9) . . ? C2 C1 S1 113.17(15) . . ? C2 C1 Cl1 126.86(16) . . ? S1 C1 Cl1 119.95(11) . . ? C1 C2 C3 111.36(17) . . ? C1 C2 H2A 124.3 . . ? C3 C2 H2A 124.3 . . ? C4 C3 C2 113.40(16) . . ? C4 C3 H3A 123.3 . . ? C2 C3 H3A 123.3 . . ? C3 C4 C5 130.23(17) . . ? C3 C4 S1 111.22(14) . . ? C5 C4 S1 118.48(13) . . ? O1 C5 C4 120.16(17) . . ? O1 C5 C6 122.75(17) . . ? C4 C5 C6 117.08(16) . . ? C7 C6 C5 122.14(17) . . ? C7 C6 H6A 118.9 . . ? C5 C6 H6A 118.9 . . ? C6 C7 C8 126.99(17) . . ? C6 C7 H7A 116.5 . . ? C8 C7 H7A 116.5 . . ? C13 C8 C9 118.43(19) . . ? C13 C8 C7 119.70(19) . . ? C9 C8 C7 121.87(16) . . ? C10 C9 C8 120.36(17) . . ? C10 C9 H9A 119.8 . . ? C8 C9 H9A 119.8 . . ? C9 C10 C11 119.6(2) . . ? C9 C10 Cl2 120.75(15) . . ? C11 C10 Cl2 119.64(16) . . ? F1 C11 C12 119.60(19) . . ? F1 C11 C10 119.3(2) . . ? C12 C11 C10 121.1(2) . . ? C11 C12 C13 119.51(19) . . ? C11 C12 H12A 120.2 . . ? C13 C12 H12A 120.2 . . ? C12 C13 C8 121.0(2) . . ? C12 C13 H13A 119.5 . . ? C8 C13 H13A 119.5 . . ? 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 C4 S1 C1 C2 -0.16(16) . . . . ? C4 S1 C1 Cl1 -179.00(12) . . . . ? S1 C1 C2 C3 0.0(2) . . . . ? Cl1 C1 C2 C3 178.78(15) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C5 -177.07(18) . . . . ? C2 C3 C4 S1 -0.3(2) . . . . ? C1 S1 C4 C3 0.24(15) . . . . ? C1 S1 C4 C5 177.47(14) . . . . ? C3 C4 C5 O1 177.44(19) . . . . ? S1 C4 C5 O1 0.8(2) . . . . ? C3 C4 C5 C6 -3.4(3) . . . . ? S1 C4 C5 C6 -179.97(13) . . . . ? O1 C5 C6 C7 5.6(3) . . . . ? C4 C5 C6 C7 -173.59(18) . . . . ? C5 C6 C7 C8 179.45(17) . . . . ? C6 C7 C8 C13 -174.3(2) . . . . ? C6 C7 C8 C9 5.9(3) . . . . ? C13 C8 C9 C10 0.4(3) . . . . ? C7 C8 C9 C10 -179.77(17) . . . . ? C8 C9 C10 C11 -0.2(3) . . . . ? C8 C9 C10 Cl2 179.22(14) . . . . ? C9 C10 C11 F1 179.88(17) . . . . ? Cl2 C10 C11 F1 0.5(3) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? Cl2 C10 C11 C12 -179.12(17) . . . . ? F1 C11 C12 C13 179.8(2) . . . . ? C10 C11 C12 C13 -0.6(3) . . . . ? C11 C12 C13 C8 0.8(4) . . . . ? C9 C8 C13 C12 -0.7(3) . . . . ? C7 C8 C13 C12 179.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.11 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.197 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.054 #============================================================================== data_3e _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H7 Br Cl F O S' _chemical_formula_sum 'C13 H7 Br Cl F O S' _chemical_formula_weight 345.61 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' 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' '-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 7.476(2) _cell_length_b 11.724(3) _cell_length_c 30.009(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2630.4(13) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2826 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 25.32 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.745 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 3.482 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.2373 _exptl_absorpt_correction_T_max 0.7516 _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 APEX Duo CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 16116 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0485 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 29.97 _reflns_number_total 3816 _reflns_number_gt 1935 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 2009) ; _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. ; _iucr_refine_instructions_details ; TITL mo_ch14_0m in Pbca (RT) CELL 0.71073 7.4759 11.7245 30.0094 90.000 90.000 90.000 ZERR 8.00 0.0021 0.0032 0.0081 0.000 0.000 0.000 LATT 1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H O F S CL BR UNIT 104 56 8 8 8 8 8 TEMP 24.000 SIZE 0.087 0.283 0.58 L.S. 10 BOND $H FMAP 2 1 60 PLAN 20 ACTA CONF WGHT 0.0590 0.4999 FVAR 0.30882 BR1 7 1.075093 0.810480 0.172154 11.00000 0.10604 0.06581 = 0.08583 -0.01361 -0.00703 -0.00803 CL1 6 0.547014 0.397128 -0.136245 11.00000 0.07575 0.06786 = 0.07754 -0.01742 -0.00675 0.00394 S1 5 0.612788 0.314589 -0.044209 11.00000 0.07241 0.03922 = 0.08912 -0.00854 -0.00920 -0.00402 F1 4 1.132319 0.663780 0.253597 11.00000 0.14694 0.12369 = 0.06792 -0.01426 -0.02823 0.01409 O1 3 0.679178 0.261863 0.049754 11.00000 0.08678 0.04520 = 0.09198 0.00322 -0.00117 -0.00870 C1 1 0.624478 0.420280 -0.083138 11.00000 0.05249 0.04969 = 0.07088 -0.00889 0.00187 0.00631 C2 1 0.693581 0.519383 -0.066959 11.00000 0.07572 0.04758 = 0.07738 -0.00246 0.00335 -0.01216 AFIX 43 H2A 2 0.708684 0.585423 -0.083708 11.00000 -1.20000 AFIX 0 C3 1 0.739041 0.509165 -0.021847 11.00000 0.06458 0.04373 = 0.07311 -0.00542 -0.00257 -0.00918 AFIX 43 H3A 2 0.788012 0.568469 -0.005272 11.00000 -1.20000 AFIX 0 C4 1 0.704415 0.403487 -0.004536 11.00000 0.04346 0.04121 = 0.07370 -0.00874 -0.00083 0.00109 C5 1 0.725352 0.360218 0.040695 11.00000 0.04634 0.04481 = 0.08361 -0.00058 0.00422 0.00563 C6 1 0.802868 0.438389 0.073999 11.00000 0.05689 0.04377 = 0.07155 0.00100 0.00413 -0.00046 AFIX 43 H6A 2 0.825197 0.513624 0.065908 11.00000 -1.20000 AFIX 0 C7 1 0.841666 0.405158 0.114941 11.00000 0.05429 0.04529 = 0.07556 0.00544 0.00833 0.00259 AFIX 43 H7A 2 0.818580 0.329194 0.121760 11.00000 -1.20000 AFIX 0 C8 1 0.917028 0.475008 0.150694 11.00000 0.05403 0.05845 = 0.05932 0.00699 0.00880 0.00815 C9 1 0.952257 0.591031 0.145334 11.00000 0.05403 0.05555 = 0.05127 0.00472 0.00260 0.00519 AFIX 43 H9A 2 0.927441 0.626225 0.118258 11.00000 -1.20000 AFIX 0 C10 1 1.023509 0.653931 0.179814 11.00000 0.05753 0.06215 = 0.05630 0.00161 0.00417 0.00649 C11 1 1.061051 0.601981 0.219973 11.00000 0.08839 0.09463 = 0.04858 -0.01200 -0.00440 0.01597 C12 1 1.030883 0.488209 0.226133 11.00000 0.10874 0.09636 = 0.06050 0.02064 -0.00135 0.01863 AFIX 43 H12A 2 1.059568 0.453939 0.253153 11.00000 -1.20000 AFIX 0 C13 1 0.957217 0.423897 0.191899 11.00000 0.08849 0.07098 = 0.06887 0.01886 0.00943 0.01088 AFIX 43 H13A 2 0.934351 0.346719 0.196227 11.00000 -1.20000 HKLF 4 REM mo_ch14_0m in Pbca (RT) REM R1 = 0.0444 for 1935 Fo > 4sig(Fo) and 0.1080 for all 3816 data REM 163 parameters refined using 0 restraints END WGHT 0.0590 0.4999 REM Highest difference peak 0.350, deepest hole -0.449, 1-sigma level 0.056 Q1 1 1.1399 0.7855 0.1975 11.00000 0.05 0.35 Q2 1 1.1831 0.7797 0.1865 11.00000 0.05 0.31 Q3 1 1.0003 0.7757 0.1984 11.00000 0.05 0.28 Q4 1 0.9439 0.7941 0.1848 11.00000 0.05 0.22 Q5 1 0.5890 0.4025 -0.0625 11.00000 0.05 0.22 Q6 1 0.6734 0.5287 -0.0392 11.00000 0.05 0.19 Q7 1 0.5685 0.3118 0.0395 11.00000 0.05 0.18 Q8 1 0.4640 0.3196 -0.0996 11.00000 0.05 0.18 Q9 1 0.8977 0.4591 0.1787 11.00000 0.05 0.18 Q10 1 0.9528 0.4650 0.1587 11.00000 0.05 0.18 Q11 1 1.1205 0.8070 0.1350 11.00000 0.05 0.18 Q12 1 0.5915 0.4210 -0.0975 11.00000 0.05 0.18 Q13 1 0.6879 0.4641 -0.0784 11.00000 0.05 0.16 Q14 1 0.6300 0.3919 -0.1157 11.00000 0.05 0.16 Q15 1 1.0705 0.8634 0.1842 11.00000 0.05 0.16 Q16 1 0.6629 0.3827 -0.0186 11.00000 0.05 0.16 Q17 1 0.6840 0.4102 0.0156 11.00000 0.05 0.15 Q18 1 0.6574 0.3182 -0.0199 11.00000 0.05 0.15 Q19 1 1.2103 0.8192 0.1389 11.00000 0.05 0.15 Q20 1 0.9793 0.6194 0.1199 11.00000 0.05 0.15 ; _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^)+(0.0590P)^2^+0.4999P] 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_number_reflns 3816 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1080 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1097 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.001 _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 Br1 Br 1.07509(6) 0.81048(3) 0.172154(15) 0.0859(2) Uani 1 1 d . . . Cl1 Cl 0.54701(12) 0.39713(8) -0.13624(3) 0.0737(3) Uani 1 1 d . . . S1 S 0.61279(12) 0.31459(6) -0.04421(3) 0.0669(3) Uani 1 1 d . . . F1 F 1.1323(4) 0.6638(2) 0.25360(8) 0.1129(8) Uani 1 1 d . . . O1 O 0.6792(3) 0.26186(18) 0.04975(8) 0.0747(6) Uani 1 1 d . . . C1 C 0.6245(4) 0.4203(2) -0.08314(11) 0.0577(8) Uani 1 1 d . . . C2 C 0.6936(5) 0.5194(3) -0.06696(12) 0.0669(9) Uani 1 1 d . . . H2A H 0.7087 0.5854 -0.0837 0.080 Uiso 1 1 calc R . . C3 C 0.7390(4) 0.5092(2) -0.02185(11) 0.0605(8) Uani 1 1 d . . . H3A H 0.7880 0.5685 -0.0053 0.073 Uiso 1 1 calc R . . C4 C 0.7044(4) 0.4035(2) -0.00454(11) 0.0528(7) Uani 1 1 d . . . C5 C 0.7254(4) 0.3602(3) 0.04069(11) 0.0583(8) Uani 1 1 d . . . C6 C 0.8029(4) 0.4384(2) 0.07400(11) 0.0574(8) Uani 1 1 d . . . H6A H 0.8252 0.5136 0.0659 0.069 Uiso 1 1 calc R . . C7 C 0.8417(4) 0.4052(3) 0.11494(11) 0.0584(8) Uani 1 1 d . . . H7A H 0.8186 0.3292 0.1218 0.070 Uiso 1 1 calc R . . C8 C 0.9170(4) 0.4750(3) 0.15069(11) 0.0573(8) Uani 1 1 d . . . C9 C 0.9523(4) 0.5910(3) 0.14533(10) 0.0536(7) Uani 1 1 d . . . H9A H 0.9274 0.6262 0.1183 0.064 Uiso 1 1 calc R . . C10 C 1.0235(4) 0.6539(3) 0.17981(11) 0.0587(8) Uani 1 1 d . . . C11 C 1.0611(5) 0.6020(4) 0.21997(11) 0.0772(11) Uani 1 1 d . . . C12 C 1.0309(6) 0.4882(4) 0.22613(14) 0.0885(12) Uani 1 1 d . . . H12A H 1.0596 0.4539 0.2532 0.106 Uiso 1 1 calc R . . C13 C 0.9572(5) 0.4239(3) 0.19190(13) 0.0761(10) Uani 1 1 d . . . H13A H 0.9344 0.3467 0.1962 0.091 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 Br1 0.1060(4) 0.0658(3) 0.0858(3) -0.01361(19) -0.0070(2) -0.0080(2) Cl1 0.0757(6) 0.0679(5) 0.0775(6) -0.0174(4) -0.0068(4) 0.0039(4) S1 0.0724(6) 0.0392(4) 0.0891(7) -0.0085(4) -0.0092(5) -0.0040(4) F1 0.147(2) 0.124(2) 0.0679(16) -0.0143(14) -0.0282(15) 0.0141(17) O1 0.0868(16) 0.0452(12) 0.0920(17) 0.0032(12) -0.0012(13) -0.0087(12) C1 0.0525(17) 0.0497(16) 0.071(2) -0.0089(14) 0.0019(15) 0.0063(14) C2 0.076(2) 0.0476(16) 0.077(3) -0.0025(16) 0.0034(18) -0.0122(16) C3 0.0646(19) 0.0437(15) 0.073(2) -0.0054(15) -0.0026(16) -0.0092(15) C4 0.0435(15) 0.0412(14) 0.074(2) -0.0087(14) -0.0008(14) 0.0011(12) C5 0.0463(16) 0.0448(15) 0.084(2) -0.0006(16) 0.0042(15) 0.0056(14) C6 0.0569(17) 0.0438(15) 0.072(2) 0.0010(15) 0.0041(15) -0.0005(14) C7 0.0543(17) 0.0453(16) 0.076(2) 0.0054(15) 0.0083(16) 0.0026(15) C8 0.0540(18) 0.0585(18) 0.0593(19) 0.0070(15) 0.0088(14) 0.0082(15) C9 0.0540(17) 0.0556(17) 0.0513(18) 0.0047(14) 0.0026(14) 0.0052(14) C10 0.0575(19) 0.0622(18) 0.056(2) 0.0016(15) 0.0042(15) 0.0065(16) C11 0.088(3) 0.095(3) 0.049(2) -0.0120(19) -0.0044(18) 0.016(2) C12 0.109(3) 0.096(3) 0.060(2) 0.021(2) -0.001(2) 0.019(3) C13 0.088(3) 0.071(2) 0.069(2) 0.0189(19) 0.009(2) 0.011(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 Br1 C10 1.890(4) . ? Cl1 C1 1.717(3) . ? S1 C1 1.705(3) . ? S1 C4 1.724(3) . ? F1 C11 1.352(4) . ? O1 C5 1.234(4) . ? C1 C2 1.361(4) . ? C2 C3 1.401(5) . ? C2 H2A 0.9300 . ? C3 C4 1.368(4) . ? C3 H3A 0.9300 . ? C4 C5 1.457(5) . ? C5 C6 1.475(4) . ? C6 C7 1.321(4) . ? C6 H6A 0.9300 . ? C7 C8 1.463(5) . ? C7 H7A 0.9300 . ? C8 C9 1.395(4) . ? C8 C13 1.407(5) . ? C9 C10 1.378(5) . ? C9 H9A 0.9300 . ? C10 C11 1.379(5) . ? C11 C12 1.365(6) . ? C12 C13 1.388(6) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? 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 S1 C4 90.77(15) . . ? C2 C1 S1 113.3(3) . . ? C2 C1 Cl1 126.4(3) . . ? S1 C1 Cl1 120.24(18) . . ? C1 C2 C3 111.3(3) . . ? C1 C2 H2A 124.3 . . ? C3 C2 H2A 124.3 . . ? C4 C3 C2 113.5(3) . . ? C4 C3 H3A 123.3 . . ? C2 C3 H3A 123.3 . . ? C3 C4 C5 130.4(3) . . ? C3 C4 S1 111.1(2) . . ? C5 C4 S1 118.4(2) . . ? O1 C5 C4 120.0(3) . . ? O1 C5 C6 122.8(3) . . ? C4 C5 C6 117.2(3) . . ? C7 C6 C5 122.2(3) . . ? C7 C6 H6A 118.9 . . ? C5 C6 H6A 118.9 . . ? C6 C7 C8 127.0(3) . . ? C6 C7 H7A 116.5 . . ? C8 C7 H7A 116.5 . . ? C9 C8 C13 118.5(3) . . ? C9 C8 C7 122.3(3) . . ? C13 C8 C7 119.3(3) . . ? C10 C9 C8 120.6(3) . . ? C10 C9 H9A 119.7 . . ? C8 C9 H9A 119.7 . . ? C9 C10 C11 119.9(3) . . ? C9 C10 Br1 120.5(2) . . ? C11 C10 Br1 119.6(3) . . ? F1 C11 C12 119.2(4) . . ? F1 C11 C10 119.7(4) . . ? C12 C11 C10 121.1(4) . . ? C11 C12 C13 119.7(4) . . ? C11 C12 H12A 120.1 . . ? C13 C12 H12A 120.1 . . ? C12 C13 C8 120.3(4) . . ? C12 C13 H13A 119.9 . . ? C8 C13 H13A 119.9 . . ? 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 C4 S1 C1 C2 -0.4(3) . . . . ? C4 S1 C1 Cl1 -178.6(2) . . . . ? S1 C1 C2 C3 0.3(4) . . . . ? Cl1 C1 C2 C3 178.3(2) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C2 C3 C4 C5 -177.3(3) . . . . ? C2 C3 C4 S1 -0.4(4) . . . . ? C1 S1 C4 C3 0.5(2) . . . . ? C1 S1 C4 C5 177.7(2) . . . . ? C3 C4 C5 O1 177.2(3) . . . . ? S1 C4 C5 O1 0.5(4) . . . . ? C3 C4 C5 C6 -2.9(5) . . . . ? S1 C4 C5 C6 -179.6(2) . . . . ? O1 C5 C6 C7 5.7(5) . . . . ? C4 C5 C6 C7 -174.2(3) . . . . ? C5 C6 C7 C8 -179.4(3) . . . . ? C6 C7 C8 C9 2.2(5) . . . . ? C6 C7 C8 C13 -177.2(3) . . . . ? C13 C8 C9 C10 -0.5(4) . . . . ? C7 C8 C9 C10 -179.9(3) . . . . ? C8 C9 C10 C11 0.2(5) . . . . ? C8 C9 C10 Br1 178.9(2) . . . . ? C9 C10 C11 F1 179.5(3) . . . . ? Br1 C10 C11 F1 0.8(5) . . . . ? C9 C10 C11 C12 0.8(6) . . . . ? Br1 C10 C11 C12 -177.8(3) . . . . ? F1 C11 C12 C13 179.8(4) . . . . ? C10 C11 C12 C13 -1.6(6) . . . . ? C11 C12 C13 C8 1.3(6) . . . . ? C9 C8 C13 C12 -0.3(5) . . . . ? C7 C8 C13 C12 179.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.97 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.350 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.056 #============================================================================== data_3f _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H8 Cl2 O S' _chemical_formula_sum 'C13 H8 Cl2 O S' _chemical_formula_weight 283.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.5437(10) _cell_length_b 7.5227(6) _cell_length_c 11.7604(9) _cell_angle_alpha 90.00 _cell_angle_beta 104.7210(10) _cell_angle_gamma 90.00 _cell_volume 1244.44(16) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4707 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 29.01 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.667 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.7332 _exptl_absorpt_correction_T_max 0.9461 _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 APEX Duo CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 11650 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2829 _reflns_number_gt 2312 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 2009) ; _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. ; _iucr_refine_instructions_details ; TITL mo_ch22b_0m in P2(1)/c (RT) CELL 0.71073 14.5437 7.5227 11.7604 90.000 104.721 90.000 ZERR 4.00 0.0010 0.0006 0.0009 0.000 0.001 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H O S CL UNIT 52 32 4 4 8 TEMP 24.000 SIZE 0.084 0.234 0.496 L.S. 10 BOND $H FMAP 2 2 60 PLAN 20 OMIT -4 55 OMIT 0 0 4 OMIT -10 1 5 OMIT 1 1 8 OMIT 1 0 8 OMIT 0 0 2 OMIT 2 0 8 OMIT -2 5 3 OMIT -2 5 4 ACTA CONF WGHT 0.0573 0.2014 FVAR 0.60379 CL1 5 1.285829 0.452821 0.698037 11.00000 0.04261 0.07306 = 0.05565 -0.00267 0.00330 -0.00545 CL2 5 0.631329 -0.025687 0.060485 11.00000 0.06374 0.10309 = 0.04922 -0.01428 0.01105 -0.00790 S1 4 1.089415 0.369782 0.711479 11.00000 0.05055 0.07188 = 0.03329 -0.00505 0.00907 -0.00974 O1 3 0.888974 0.288588 0.694333 11.00000 0.05565 0.08024 = 0.04425 -0.00715 0.01948 -0.00782 C1 1 1.173239 0.377870 0.632991 11.00000 0.04061 0.04649 = 0.04325 0.00218 0.00722 0.00106 C2 1 1.141090 0.322525 0.520252 11.00000 0.04653 0.06472 = 0.04562 -0.00993 0.01676 -0.00155 AFIX 43 H2A 2 1.177639 0.319158 0.465876 11.00000 -1.20000 AFIX 0 C3 1 1.044573 0.270517 0.496137 11.00000 0.04642 0.05799 = 0.03863 -0.00844 0.00841 -0.00217 AFIX 43 H3A 2 1.010332 0.228774 0.423222 11.00000 -1.20000 AFIX 0 C4 1 1.006702 0.287708 0.590561 11.00000 0.04356 0.04430 = 0.03521 -0.00072 0.00673 -0.00029 C5 1 0.910107 0.256089 0.601377 11.00000 0.04631 0.04604 = 0.03815 0.00287 0.01108 -0.00016 C6 1 0.841341 0.182519 0.497809 11.00000 0.04362 0.05428 = 0.03976 0.00064 0.00995 -0.00156 AFIX 43 H6A 2 0.858171 0.175104 0.426771 11.00000 -1.20000 AFIX 0 C7 1 0.756128 0.126625 0.503217 11.00000 0.04708 0.05209 = 0.04220 0.00185 0.01350 -0.00082 AFIX 43 H7A 2 0.741435 0.137271 0.575400 11.00000 -1.20000 AFIX 0 C8 1 0.682756 0.049651 0.406543 11.00000 0.04017 0.04458 = 0.04900 0.00296 0.01124 0.00075 C9 1 0.690205 0.051085 0.290697 11.00000 0.03811 0.04785 = 0.04949 -0.00004 0.01152 -0.00215 AFIX 43 H9A 2 0.742480 0.103427 0.272152 11.00000 -1.20000 AFIX 0 C10 1 0.619307 -0.025876 0.203569 11.00000 0.04364 0.04999 = 0.04944 -0.00295 0.00916 0.00401 C11 1 0.540543 -0.105238 0.228157 11.00000 0.03939 0.05383 = 0.06687 -0.00685 0.00528 -0.00310 AFIX 43 H11A 2 0.493500 -0.156426 0.168479 11.00000 -1.20000 AFIX 0 C12 1 0.533289 -0.106857 0.342122 11.00000 0.04115 0.06252 = 0.07362 0.00318 0.01694 -0.00940 AFIX 43 H12A 2 0.480891 -0.160093 0.359805 11.00000 -1.20000 AFIX 0 C13 1 0.602973 -0.030246 0.431274 11.00000 0.04601 0.06154 = 0.05689 0.00449 0.01968 -0.00504 AFIX 43 H13A 2 0.596773 -0.031841 0.508049 11.00000 -1.20000 HKLF 4 1 0 0 1 0 -1 0 1 0 0 REM mo_ch22b_0m in P2(1)/c (RT) REM R1 = 0.0299 for 2312 Fo > 4sig(Fo) and 0.0385 for all 2829 data REM 154 parameters refined using 0 restraints END WGHT 0.0573 0.2014 REM Highest difference peak 0.212, deepest hole -0.217, 1-sigma level 0.043 Q1 1 0.8741 0.2177 0.5441 11.00000 0.05 0.21 Q2 1 0.6368 -0.1325 0.1023 11.00000 0.05 0.20 Q3 1 1.0202 0.3168 0.5415 11.00000 0.05 0.19 Q4 1 0.9636 0.2484 0.6011 11.00000 0.05 0.19 Q5 1 1.0286 0.2458 0.5565 11.00000 0.05 0.18 Q6 1 0.6464 0.0105 0.4254 11.00000 0.05 0.18 Q7 1 0.7162 0.0696 0.4463 11.00000 0.05 0.18 Q8 1 0.6545 0.0054 0.2473 11.00000 0.05 0.18 Q9 1 0.8066 0.1236 0.4952 11.00000 0.05 0.17 Q10 1 1.0351 0.3153 0.6409 11.00000 0.05 0.17 Q11 1 0.5719 -0.0250 0.2198 11.00000 0.05 0.17 Q12 1 0.5621 -0.0457 0.3812 11.00000 0.05 0.17 Q13 1 1.1683 0.3086 0.5881 11.00000 0.05 0.15 Q14 1 0.6226 -0.0252 0.1434 11.00000 0.05 0.15 Q15 1 1.1419 0.3594 0.6775 11.00000 0.05 0.15 Q16 1 1.2795 0.4092 0.7650 11.00000 0.05 0.14 Q17 1 0.9086 0.2281 0.6495 11.00000 0.05 0.14 Q18 1 1.1045 0.2964 0.4994 11.00000 0.05 0.14 Q19 1 0.4862 -0.2345 0.1792 11.00000 0.05 0.13 Q20 1 0.4884 -0.2430 0.3374 11.00000 0.05 0.13 ; _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^)+(0.0573P)^2^+0.2014P] 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_number_reflns 2829 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.1010 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _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 Cl1 Cl 1.28583(3) 0.45282(7) 0.69804(4) 0.05877(16) Uani 1 1 d . . . Cl2 Cl 0.63133(4) -0.02569(9) 0.06048(4) 0.07262(18) Uani 1 1 d . . . S1 S 1.08941(3) 0.36978(6) 0.71148(4) 0.05219(15) Uani 1 1 d . . . O1 O 0.88897(9) 0.28859(19) 0.69433(11) 0.0588(3) Uani 1 1 d . . . C1 C 1.17324(11) 0.3779(2) 0.63299(15) 0.0441(4) Uani 1 1 d . . . C2 C 1.14109(12) 0.3225(2) 0.52025(16) 0.0514(4) Uani 1 1 d . . . H2A H 1.1776 0.3192 0.4659 0.062 Uiso 1 1 calc R . . C3 C 1.04457(11) 0.2705(2) 0.49614(15) 0.0481(4) Uani 1 1 d . . . H3A H 1.0103 0.2288 0.4232 0.058 Uiso 1 1 calc R . . C4 C 1.00670(11) 0.2877(2) 0.59056(14) 0.0416(3) Uani 1 1 d . . . C5 C 0.91011(11) 0.2561(2) 0.60138(14) 0.0434(3) Uani 1 1 d . . . C6 C 0.84134(11) 0.1825(2) 0.49781(15) 0.0460(4) Uani 1 1 d . . . H6A H 0.8582 0.1751 0.4268 0.055 Uiso 1 1 calc R . . C7 C 0.75613(12) 0.1266(2) 0.50322(15) 0.0467(4) Uani 1 1 d . . . H7A H 0.7414 0.1373 0.5754 0.056 Uiso 1 1 calc R . . C8 C 0.68276(11) 0.0497(2) 0.40654(15) 0.0446(4) Uani 1 1 d . . . C9 C 0.69020(11) 0.0511(2) 0.29070(15) 0.0451(4) Uani 1 1 d . . . H9A H 0.7425 0.1034 0.2722 0.054 Uiso 1 1 calc R . . C10 C 0.61931(11) -0.0259(2) 0.20357(16) 0.0482(4) Uani 1 1 d . . . C11 C 0.54054(12) -0.1052(2) 0.22816(18) 0.0549(5) Uani 1 1 d . . . H11A H 0.4935 -0.1564 0.1685 0.066 Uiso 1 1 calc R . . C12 C 0.53329(13) -0.1069(3) 0.3421(2) 0.0587(5) Uani 1 1 d . . . H12A H 0.4809 -0.1601 0.3598 0.070 Uiso 1 1 calc R . . C13 C 0.60297(12) -0.0302(2) 0.43127(18) 0.0536(4) Uani 1 1 d . . . H13A H 0.5968 -0.0318 0.5080 0.064 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 Cl1 0.0426(2) 0.0731(3) 0.0556(3) -0.0027(2) 0.00330(19) -0.00545(18) Cl2 0.0637(3) 0.1031(4) 0.0492(3) -0.0143(3) 0.0111(2) -0.0079(3) S1 0.0506(3) 0.0719(3) 0.0333(2) -0.00505(18) 0.00907(18) -0.0097(2) O1 0.0557(7) 0.0802(9) 0.0443(7) -0.0071(6) 0.0195(6) -0.0078(6) C1 0.0406(8) 0.0465(8) 0.0433(9) 0.0022(6) 0.0072(6) 0.0011(6) C2 0.0465(8) 0.0647(10) 0.0456(9) -0.0099(8) 0.0168(7) -0.0016(7) C3 0.0464(8) 0.0580(9) 0.0386(8) -0.0084(7) 0.0084(7) -0.0022(7) C4 0.0436(8) 0.0443(7) 0.0352(8) -0.0007(6) 0.0067(6) -0.0003(6) C5 0.0463(8) 0.0460(8) 0.0381(8) 0.0029(7) 0.0111(7) -0.0002(6) C6 0.0436(8) 0.0543(8) 0.0398(8) 0.0006(7) 0.0100(7) -0.0016(7) C7 0.0471(8) 0.0521(8) 0.0422(9) 0.0018(7) 0.0135(7) -0.0008(7) C8 0.0402(8) 0.0446(8) 0.0490(9) 0.0030(7) 0.0112(7) 0.0007(6) C9 0.0381(7) 0.0479(8) 0.0495(10) 0.0000(7) 0.0115(7) -0.0021(6) C10 0.0436(8) 0.0500(8) 0.0494(10) -0.0030(7) 0.0092(7) 0.0040(7) C11 0.0394(8) 0.0538(9) 0.0669(12) -0.0068(8) 0.0053(8) -0.0031(7) C12 0.0412(9) 0.0625(10) 0.0736(13) 0.0032(9) 0.0169(9) -0.0094(7) C13 0.0460(9) 0.0615(10) 0.0569(11) 0.0045(8) 0.0197(8) -0.0050(8) _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 Cl1 C1 1.7169(16) . ? Cl2 C10 1.7354(19) . ? S1 C1 1.7070(18) . ? S1 C4 1.7266(15) . ? O1 C5 1.233(2) . ? C1 C2 1.355(2) . ? C2 C3 1.415(2) . ? C2 H2A 0.9300 . ? C3 C4 1.365(2) . ? C3 H3A 0.9300 . ? C4 C5 1.462(2) . ? C5 C6 1.473(2) . ? C6 C7 1.325(2) . ? C6 H6A 0.9300 . ? C7 C8 1.466(2) . ? C7 H7A 0.9300 . ? C8 C9 1.394(2) . ? C8 C13 1.401(2) . ? C9 C10 1.383(2) . ? C9 H9A 0.9300 . ? C10 C11 1.386(3) . ? C11 C12 1.371(3) . ? C11 H11A 0.9300 . ? C12 C13 1.385(3) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? 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 S1 C4 90.64(8) . . ? C2 C1 S1 113.70(13) . . ? C2 C1 Cl1 126.15(14) . . ? S1 C1 Cl1 120.14(10) . . ? C1 C2 C3 111.06(16) . . ? C1 C2 H2A 124.5 . . ? C3 C2 H2A 124.5 . . ? C4 C3 C2 113.30(15) . . ? C4 C3 H3A 123.4 . . ? C2 C3 H3A 123.4 . . ? C3 C4 C5 130.58(14) . . ? C3 C4 S1 111.29(12) . . ? C5 C4 S1 118.06(12) . . ? O1 C5 C4 120.43(14) . . ? O1 C5 C6 122.53(15) . . ? C4 C5 C6 117.04(14) . . ? C7 C6 C5 121.74(16) . . ? C7 C6 H6A 119.1 . . ? C5 C6 H6A 119.1 . . ? C6 C7 C8 126.38(17) . . ? C6 C7 H7A 116.8 . . ? C8 C7 H7A 116.8 . . ? C9 C8 C13 118.70(15) . . ? C9 C8 C7 122.19(15) . . ? C13 C8 C7 119.10(16) . . ? C10 C9 C8 119.51(15) . . ? C10 C9 H9A 120.2 . . ? C8 C9 H9A 120.2 . . ? C9 C10 C11 121.74(17) . . ? C9 C10 Cl2 118.58(14) . . ? C11 C10 Cl2 119.67(14) . . ? C12 C11 C10 118.74(16) . . ? C12 C11 H11A 120.6 . . ? C10 C11 H11A 120.6 . . ? C11 C12 C13 120.87(16) . . ? C11 C12 H12A 119.6 . . ? C13 C12 H12A 119.6 . . ? C12 C13 C8 120.43(18) . . ? C12 C13 H13A 119.8 . . ? C8 C13 H13A 119.8 . . ? 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 C4 S1 C1 C2 0.36(14) . . . . ? C4 S1 C1 Cl1 179.89(10) . . . . ? S1 C1 C2 C3 -0.3(2) . . . . ? Cl1 C1 C2 C3 -179.74(13) . . . . ? C1 C2 C3 C4 0.0(2) . . . . ? C2 C3 C4 C5 177.17(16) . . . . ? C2 C3 C4 S1 0.3(2) . . . . ? C1 S1 C4 C3 -0.37(13) . . . . ? C1 S1 C4 C5 -177.68(13) . . . . ? C3 C4 C5 O1 -176.26(17) . . . . ? S1 C4 C5 O1 0.4(2) . . . . ? C3 C4 C5 C6 4.5(3) . . . . ? S1 C4 C5 C6 -178.76(11) . . . . ? O1 C5 C6 C7 -8.5(3) . . . . ? C4 C5 C6 C7 170.71(15) . . . . ? C5 C6 C7 C8 -179.29(15) . . . . ? C6 C7 C8 C9 -9.9(3) . . . . ? C6 C7 C8 C13 169.28(17) . . . . ? C13 C8 C9 C10 -0.1(2) . . . . ? C7 C8 C9 C10 179.08(15) . . . . ? C8 C9 C10 C11 -0.1(2) . . . . ? C8 C9 C10 Cl2 -178.90(12) . . . . ? C9 C10 C11 C12 0.0(3) . . . . ? Cl2 C10 C11 C12 178.79(14) . . . . ? C10 C11 C12 C13 0.2(3) . . . . ? C11 C12 C13 C8 -0.4(3) . . . . ? C9 C8 C13 C12 0.3(3) . . . . ? C7 C8 C13 C12 -178.86(16) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.212 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.043 #============================================================================== data_3g _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H7 Br Cl F O S' _chemical_formula_sum 'C13 H7 Br Cl F O S' _chemical_formula_weight 345.61 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.8704(7) _cell_length_b 31.953(6) _cell_length_c 10.273(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.243(3) _cell_angle_gamma 90.00 _cell_volume 1265.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 5747 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 29.76 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.89 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.814 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 3.619 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.1406 _exptl_absorpt_correction_T_max 0.7436 _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0(1)K. ; _diffrn_ambient_temperature 100.0(1) _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 APEX Duo CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 2855 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2855 _reflns_number_gt 2624 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 2009) ; _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^+5.4749P] 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_number_reflns 2855 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1272 _refine_ls_wR_factor_gt 0.1245 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max <0.001 _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 Br1 Br 0.03181(12) 0.495663(15) 0.26487(5) 0.03367(17) Uani 1 1 d . . . Cl1 Cl 0.3924(4) 0.07855(4) 0.42968(14) 0.0390(3) Uani 1 1 d . . . S1 S 0.5516(3) 0.16294(3) 0.53812(11) 0.0238(2) Uani 1 1 d . . . F1 F 0.6351(8) 0.39899(8) 0.6197(3) 0.0352(7) Uani 1 1 d . . . O1 O 0.6938(10) 0.24843(10) 0.6188(3) 0.0352(8) Uani 1 1 d . . . C1 C 0.3615(11) 0.13210(13) 0.4158(5) 0.0252(9) Uani 1 1 d . . . C2 C 0.1993(11) 0.15391(13) 0.3151(4) 0.0253(9) Uani 1 1 d . . . H2A H 0.0806 0.1415 0.2397 0.030 Uiso 1 1 calc R . . C3 C 0.2294(11) 0.19758(14) 0.3365(4) 0.0248(9) Uani 1 1 d . . . H3A H 0.1320 0.2180 0.2766 0.030 Uiso 1 1 calc R . . C4 C 0.4141(11) 0.20725(12) 0.4528(4) 0.0214(8) Uani 1 1 d . . . C5 C 0.5129(13) 0.24739(14) 0.5132(4) 0.0281(10) Uani 1 1 d . . . C6 C 0.3855(13) 0.28578(15) 0.4427(5) 0.0303(10) Uani 1 1 d . . . H6A H 0.2541 0.2834 0.3602 0.036 Uiso 1 1 calc R . . C7 C 0.4540(12) 0.32333(15) 0.4941(4) 0.0273(9) Uani 1 1 d . . . H7A H 0.5893 0.3240 0.5761 0.033 Uiso 1 1 calc R . . C8 C 0.3441(13) 0.36354(14) 0.4384(4) 0.0283(10) Uani 1 1 d . . . C9 C 0.1406(13) 0.36834(15) 0.3175(5) 0.0295(10) Uani 1 1 d . . . H9A H 0.0624 0.3440 0.2707 0.035 Uiso 1 1 calc R . . C10 C 0.0521(12) 0.40683(15) 0.2653(5) 0.0291(9) Uani 1 1 d . . . H10A H -0.0789 0.4089 0.1827 0.035 Uiso 1 1 calc R . . C11 C 0.1563(11) 0.44276(13) 0.3346(4) 0.0244(8) Uani 1 1 d . . . C12 C 0.3498(11) 0.44018(13) 0.4554(4) 0.0225(8) Uani 1 1 d . . . H12A H 0.4180 0.4647 0.5036 0.027 Uiso 1 1 calc R . . C13 C 0.4391(12) 0.40094(14) 0.5027(4) 0.0262(9) 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 Br1 0.0276(3) 0.0307(3) 0.0410(3) -0.00087(19) -0.00640(19) 0.00624(18) Cl1 0.0435(7) 0.0202(5) 0.0534(8) -0.0002(5) 0.0048(6) 0.0004(5) S1 0.0199(5) 0.0238(5) 0.0270(5) 0.0037(4) -0.0012(4) -0.0003(4) F1 0.0552(19) 0.0248(13) 0.0243(13) 0.0000(10) -0.0038(13) -0.0049(12) O1 0.042(2) 0.0310(17) 0.0323(18) -0.0026(14) 0.0006(15) -0.0060(15) C1 0.019(2) 0.0229(19) 0.033(2) 0.0013(17) 0.0045(17) -0.0007(16) C2 0.024(2) 0.026(2) 0.026(2) -0.0067(17) -0.0018(17) 0.0004(16) C3 0.025(2) 0.026(2) 0.024(2) 0.0000(16) 0.0020(17) 0.0063(16) C4 0.023(2) 0.0174(18) 0.024(2) 0.0032(15) 0.0050(16) 0.0002(15) C5 0.038(3) 0.025(2) 0.022(2) 0.0010(17) 0.0060(18) -0.0047(18) C6 0.031(2) 0.030(2) 0.030(2) 0.0008(18) 0.0012(19) -0.0025(19) C7 0.024(2) 0.032(2) 0.026(2) 0.0004(17) 0.0031(17) 0.0008(17) C8 0.037(2) 0.022(2) 0.027(2) -0.0029(17) 0.0119(19) -0.0072(18) C9 0.034(2) 0.029(2) 0.026(2) -0.0069(18) 0.0078(19) -0.0094(19) C10 0.024(2) 0.037(2) 0.027(2) -0.0095(19) 0.0006(17) -0.0028(18) C11 0.0190(19) 0.024(2) 0.031(2) -0.0035(17) 0.0027(16) 0.0002(16) C12 0.0192(19) 0.023(2) 0.026(2) -0.0085(16) 0.0031(16) -0.0049(15) C13 0.028(2) 0.029(2) 0.022(2) -0.0071(17) 0.0061(17) -0.0062(17) _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 Br1 C11 1.882(4) . ? Cl1 C1 1.720(4) . ? S1 C1 1.710(5) . ? S1 C4 1.724(4) . ? F1 C13 1.363(5) . ? O1 C5 1.237(6) . ? C1 C2 1.353(6) . ? C2 C3 1.416(6) . ? C2 H2A 0.9500 . ? C3 C4 1.371(6) . ? C3 H3A 0.9500 . ? C4 C5 1.460(6) . ? C5 C6 1.486(6) . ? C6 C7 1.328(7) . ? C6 H6A 0.9500 . ? C7 C8 1.454(6) . ? C7 H7A 0.9500 . ? C8 C13 1.398(6) . ? C8 C9 1.417(7) . ? C9 C10 1.373(7) . ? C9 H9A 0.9500 . ? C10 C11 1.391(6) . ? C10 H10A 0.9500 . ? C11 C12 1.392(6) . ? C12 C13 1.377(6) . ? C12 H12A 0.9500 . ? 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 S1 C4 90.4(2) . . ? C2 C1 S1 113.8(3) . . ? C2 C1 Cl1 126.8(4) . . ? S1 C1 Cl1 119.4(3) . . ? C1 C2 C3 111.3(4) . . ? C1 C2 H2A 124.4 . . ? C3 C2 H2A 124.4 . . ? C4 C3 C2 112.7(4) . . ? C4 C3 H3A 123.6 . . ? C2 C3 H3A 123.6 . . ? C3 C4 C5 131.6(4) . . ? C3 C4 S1 111.7(3) . . ? C5 C4 S1 116.7(3) . . ? O1 C5 C4 120.1(4) . . ? O1 C5 C6 122.8(4) . . ? C4 C5 C6 117.1(4) . . ? C7 C6 C5 120.4(4) . . ? C7 C6 H6A 119.8 . . ? C5 C6 H6A 119.8 . . ? C6 C7 C8 126.9(4) . . ? C6 C7 H7A 116.5 . . ? C8 C7 H7A 116.5 . . ? C13 C8 C9 115.0(4) . . ? C13 C8 C7 121.0(4) . . ? C9 C8 C7 124.0(4) . . ? C10 C9 C8 122.6(4) . . ? C10 C9 H9A 118.7 . . ? C8 C9 H9A 118.7 . . ? C9 C10 C11 119.3(4) . . ? C9 C10 H10A 120.4 . . ? C11 C10 H10A 120.4 . . ? C10 C11 C12 121.0(4) . . ? C10 C11 Br1 119.6(3) . . ? C12 C11 Br1 119.4(3) . . ? C13 C12 C11 117.7(4) . . ? C13 C12 H12A 121.1 . . ? C11 C12 H12A 121.1 . . ? F1 C13 C12 117.0(4) . . ? F1 C13 C8 118.6(4) . . ? C12 C13 C8 124.4(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 C4 S1 C1 C2 -0.3(4) . . . . ? C4 S1 C1 Cl1 179.3(3) . . . . ? S1 C1 C2 C3 0.2(5) . . . . ? Cl1 C1 C2 C3 -179.4(3) . . . . ? C1 C2 C3 C4 0.1(6) . . . . ? C2 C3 C4 C5 178.9(5) . . . . ? C2 C3 C4 S1 -0.4(5) . . . . ? C1 S1 C4 C3 0.4(4) . . . . ? C1 S1 C4 C5 -179.0(4) . . . . ? C3 C4 C5 O1 -177.5(5) . . . . ? S1 C4 C5 O1 1.7(6) . . . . ? C3 C4 C5 C6 2.9(7) . . . . ? S1 C4 C5 C6 -177.9(3) . . . . ? O1 C5 C6 C7 -2.2(8) . . . . ? C4 C5 C6 C7 177.4(4) . . . . ? C5 C6 C7 C8 -179.1(4) . . . . ? C6 C7 C8 C13 -179.1(5) . . . . ? C6 C7 C8 C9 0.2(8) . . . . ? C13 C8 C9 C10 1.9(7) . . . . ? C7 C8 C9 C10 -177.5(5) . . . . ? C8 C9 C10 C11 -1.9(7) . . . . ? C9 C10 C11 C12 0.3(7) . . . . ? C9 C10 C11 Br1 -179.3(4) . . . . ? C10 C11 C12 C13 1.1(6) . . . . ? Br1 C11 C12 C13 -179.4(3) . . . . ? C11 C12 C13 F1 178.6(4) . . . . ? C11 C12 C13 C8 -1.0(7) . . . . ? C9 C8 C13 F1 180.0(4) . . . . ? C7 C8 C13 F1 -0.6(7) . . . . ? C9 C8 C13 C12 -0.4(7) . . . . ? C7 C8 C13 C12 179.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.544 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.113 #============================================================================== data_3h _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H7 Cl3 O S' _chemical_formula_sum 'C13 H7 Cl3 O S' _chemical_formula_weight 317.60 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.9864(10) _cell_length_b 3.8085(3) _cell_length_c 24.6297(13) _cell_angle_alpha 90.00 _cell_angle_beta 115.264(3) _cell_angle_gamma 90.00 _cell_volume 1271.30(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 6110 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 30.05 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.866 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.6650 _exptl_absorpt_correction_T_max 0.9547 _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0(1)K. ; _diffrn_ambient_temperature 100.0(1) _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 APEX Duo CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 11375 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2894 _reflns_number_gt 2607 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 2009) ; _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^)+(0.0493P)^2^+3.8359P] 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_number_reflns 2894 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1200 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max <0.001 _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 Cl1 Cl -0.03977(5) 0.2891(2) -0.11216(3) 0.03013(19) Uani 1 1 d . . . Cl2 Cl 0.65539(6) 0.4082(2) 0.31747(3) 0.03057(19) Uani 1 1 d . . . Cl3 Cl 0.88758(5) 0.9489(2) 0.22140(3) 0.02570(18) Uani 1 1 d . . . S1 S 0.16583(5) 0.53526(18) -0.07627(3) 0.01909(17) Uani 1 1 d . . . O1 O 0.37034(15) 0.7741(7) -0.02726(10) 0.0340(5) Uani 1 1 d . . . C1 C 0.0773(2) 0.3631(8) -0.05735(12) 0.0214(5) Uani 1 1 d . . . C2 C 0.1101(2) 0.2911(8) 0.00235(13) 0.0255(6) Uani 1 1 d . . . H2A H 0.0712 0.1986 0.0199 0.031 Uiso 1 1 calc R . . C3 C 0.2112(2) 0.3763(8) 0.03398(12) 0.0255(6) Uani 1 1 d . . . H3A H 0.2468 0.3450 0.0751 0.031 Uiso 1 1 calc R . . C4 C 0.25122(19) 0.5090(8) -0.00214(12) 0.0219(6) Uani 1 1 d . . . C5 C 0.3520(2) 0.6336(10) 0.01162(13) 0.0297(7) Uani 1 1 d . . . C6 C 0.4276(2) 0.5863(9) 0.07419(13) 0.0282(6) Uani 1 1 d . . . H6A H 0.4119 0.4693 0.1021 0.034 Uiso 1 1 calc R . . C7 C 0.5190(2) 0.7143(9) 0.09012(13) 0.0291(7) Uani 1 1 d . . . H7A H 0.5309 0.8252 0.0602 0.035 Uiso 1 1 calc R . . C8 C 0.6016(2) 0.6965(9) 0.14977(12) 0.0271(7) Uani 1 1 d . . . C9 C 0.5897(2) 0.5611(8) 0.19963(13) 0.0250(6) Uani 1 1 d . . . H9A H 0.5290 0.4748 0.1953 0.030 Uiso 1 1 calc R . . C10 C 0.6697(2) 0.5594(7) 0.25454(12) 0.0208(5) Uani 1 1 d . . . C11 C 0.7623(2) 0.6758(7) 0.26257(12) 0.0211(5) Uani 1 1 d . . . H11A H 0.8156 0.6704 0.3002 0.025 Uiso 1 1 calc R . . C12 C 0.77250(18) 0.8008(7) 0.21248(12) 0.0192(5) Uani 1 1 d . . . C13 C 0.6941(2) 0.8156(8) 0.15656(12) 0.0229(6) Uani 1 1 d . . . H13A H 0.7025 0.9035 0.1238 0.028 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 Cl1 0.0268(3) 0.0284(4) 0.0265(3) -0.0021(3) 0.0030(3) -0.0121(3) Cl2 0.0401(4) 0.0231(4) 0.0274(4) 0.0033(3) 0.0134(3) -0.0069(3) Cl3 0.0224(3) 0.0255(4) 0.0254(3) -0.0018(3) 0.0067(3) -0.0042(3) S1 0.0188(3) 0.0183(3) 0.0153(3) 0.0007(2) 0.0025(2) 0.0008(2) O1 0.0191(9) 0.0504(16) 0.0291(11) -0.0019(11) 0.0070(8) -0.0026(10) C1 0.0230(12) 0.0156(13) 0.0202(12) -0.0008(11) 0.0038(10) -0.0030(10) C2 0.0349(15) 0.0174(14) 0.0235(13) 0.0018(11) 0.0118(12) -0.0014(12) C3 0.0300(14) 0.0244(15) 0.0171(12) 0.0013(11) 0.0052(11) 0.0080(12) C4 0.0189(12) 0.0241(15) 0.0162(12) -0.0014(10) 0.0014(10) 0.0070(11) C5 0.0168(12) 0.0439(19) 0.0213(13) -0.0104(13) 0.0014(10) 0.0075(13) C6 0.0266(14) 0.0343(18) 0.0231(13) -0.0009(13) 0.0099(11) 0.0007(13) C7 0.0253(14) 0.0368(18) 0.0250(14) -0.0012(13) 0.0104(12) 0.0011(13) C8 0.0165(12) 0.0410(19) 0.0206(13) -0.0073(13) 0.0047(10) 0.0052(12) C9 0.0196(12) 0.0291(16) 0.0249(13) -0.0106(12) 0.0083(11) 0.0000(11) C10 0.0274(13) 0.0111(13) 0.0216(12) 0.0001(10) 0.0084(11) 0.0003(10) C11 0.0222(12) 0.0139(13) 0.0188(12) 0.0010(10) 0.0008(10) -0.0001(10) C12 0.0156(11) 0.0148(13) 0.0227(12) -0.0018(10) 0.0040(10) 0.0016(10) C13 0.0207(12) 0.0283(16) 0.0183(12) 0.0001(11) 0.0070(10) 0.0080(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 Cl1 C1 1.720(3) . ? Cl2 C10 1.750(3) . ? Cl3 C12 1.737(3) . ? S1 C1 1.713(3) . ? S1 C4 1.728(3) . ? O1 C5 1.226(4) . ? C1 C2 1.364(4) . ? C2 C3 1.415(4) . ? C2 H2A 0.9300 . ? C3 C4 1.364(4) . ? C3 H3A 0.9300 . ? C4 C5 1.478(4) . ? C5 C6 1.483(4) . ? C6 C7 1.345(4) . ? C6 H6A 0.9300 . ? C7 C8 1.464(4) . ? C7 H7A 0.9300 . ? C8 C13 1.399(4) . ? C8 C9 1.411(4) . ? C9 C10 1.372(4) . ? C9 H9A 0.9300 . ? C10 C11 1.388(4) . ? C11 C12 1.391(4) . ? C11 H11A 0.9300 . ? C12 C13 1.378(4) . ? C13 H13A 0.9300 . ? 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 S1 C4 90.05(13) . . ? C2 C1 S1 113.9(2) . . ? C2 C1 Cl1 126.2(2) . . ? S1 C1 Cl1 119.88(16) . . ? C1 C2 C3 110.8(3) . . ? C1 C2 H2A 124.6 . . ? C3 C2 H2A 124.6 . . ? C4 C3 C2 113.0(2) . . ? C4 C3 H3A 123.5 . . ? C2 C3 H3A 123.5 . . ? C3 C4 C5 131.3(3) . . ? C3 C4 S1 112.2(2) . . ? C5 C4 S1 116.6(2) . . ? O1 C5 C4 120.6(2) . . ? O1 C5 C6 122.6(3) . . ? C4 C5 C6 116.9(3) . . ? C7 C6 C5 119.3(3) . . ? C7 C6 H6A 120.3 . . ? C5 C6 H6A 120.3 . . ? C6 C7 C8 126.5(3) . . ? C6 C7 H7A 116.7 . . ? C8 C7 H7A 116.7 . . ? C13 C8 C9 120.1(2) . . ? C13 C8 C7 118.4(3) . . ? C9 C8 C7 121.6(3) . . ? C10 C9 C8 118.6(3) . . ? C10 C9 H9A 120.7 . . ? C8 C9 H9A 120.7 . . ? C9 C10 C11 122.6(3) . . ? C9 C10 Cl2 119.3(2) . . ? C11 C10 Cl2 118.1(2) . . ? C10 C11 C12 117.7(2) . . ? C10 C11 H11A 121.1 . . ? C12 C11 H11A 121.1 . . ? C13 C12 C11 122.0(3) . . ? C13 C12 Cl3 119.4(2) . . ? C11 C12 Cl3 118.6(2) . . ? C12 C13 C8 119.0(3) . . ? C12 C13 H13A 120.5 . . ? C8 C13 H13A 120.5 . . ? 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 C4 S1 C1 C2 0.5(2) . . . . ? C4 S1 C1 Cl1 -178.3(2) . . . . ? S1 C1 C2 C3 -0.5(3) . . . . ? Cl1 C1 C2 C3 178.2(2) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C2 C3 C4 C5 179.4(3) . . . . ? C2 C3 C4 S1 0.2(3) . . . . ? C1 S1 C4 C3 -0.4(2) . . . . ? C1 S1 C4 C5 -179.7(2) . . . . ? C3 C4 C5 O1 -173.3(3) . . . . ? S1 C4 C5 O1 5.8(4) . . . . ? C3 C4 C5 C6 5.5(5) . . . . ? S1 C4 C5 C6 -175.4(2) . . . . ? O1 C5 C6 C7 2.9(5) . . . . ? C4 C5 C6 C7 -175.9(3) . . . . ? C5 C6 C7 C8 178.9(3) . . . . ? C6 C7 C8 C13 174.1(3) . . . . ? C6 C7 C8 C9 -5.4(5) . . . . ? C13 C8 C9 C10 1.9(5) . . . . ? C7 C8 C9 C10 -178.5(3) . . . . ? C8 C9 C10 C11 -2.0(4) . . . . ? C8 C9 C10 Cl2 177.6(2) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? Cl2 C10 C11 C12 -179.0(2) . . . . ? C10 C11 C12 C13 0.9(4) . . . . ? C10 C11 C12 Cl3 179.8(2) . . . . ? C11 C12 C13 C8 -1.0(4) . . . . ? Cl3 C12 C13 C8 -179.9(2) . . . . ? C9 C8 C13 C12 -0.5(5) . . . . ? C7 C8 C13 C12 179.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.078 _refine_diff_density_min -0.607 _refine_diff_density_rms 0.094 #============================================================================== data_3i _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H7 Cl3 O S' _chemical_formula_sum 'C13 H7 Cl3 O S' _chemical_formula_weight 317.60 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 30.3418(16) _cell_length_b 3.7985(2) _cell_length_c 23.4311(12) _cell_angle_alpha 90.00 _cell_angle_beta 109.2970(10) _cell_angle_gamma 90.00 _cell_volume 2548.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 5932 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 29.87 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.655 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.864 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.6243 _exptl_absorpt_correction_T_max 0.9224 _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0(1)K. ; _diffrn_ambient_temperature 100.0(1) _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 APEX Duo CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 20108 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 0.71 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5762 _reflns_number_gt 4784 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL and PLATON (Spek, 2009) ; _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^)+(0.0430P)^2^+1.8291P] 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_number_reflns 5762 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0908 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _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 Cl1A Cl 0.093954(16) 0.68505(16) -0.06520(2) 0.02051(13) Uani 1 1 d . . . Cl2A Cl 0.381686(17) 1.30070(16) 0.16993(2) 0.01960(12) Uani 1 1 d . . . Cl3A Cl 0.432059(18) 0.78103(16) -0.01689(2) 0.02133(13) Uani 1 1 d . . . S1A S 0.184580(16) 0.96269(15) -0.06895(2) 0.01528(12) Uani 1 1 d . . . O1A O 0.27733(5) 1.2248(5) -0.05823(7) 0.0209(3) Uani 1 1 d . . . C1A C 0.15210(7) 0.7749(6) -0.02917(9) 0.0157(4) Uani 1 1 d . . . C2A C 0.17707(7) 0.7043(6) 0.02960(9) 0.0173(4) Uani 1 1 d . . . H2AA H 0.1643 0.6039 0.0579 0.021 Uiso 1 1 calc R . . C3A C 0.22444(7) 0.7999(6) 0.04308(9) 0.0167(4) Uani 1 1 d . . . H3AA H 0.2474 0.7680 0.0817 0.020 Uiso 1 1 calc R . . C4A C 0.23404(7) 0.9435(6) -0.00532(9) 0.0147(4) Uani 1 1 d . . . C5A C 0.27751(7) 1.0766(6) -0.01148(9) 0.0166(4) Uani 1 1 d . . . C6A C 0.32120(7) 1.0189(6) 0.04031(9) 0.0179(5) Uani 1 1 d . . . H6AA H 0.3200 0.9317 0.0778 0.022 Uiso 1 1 calc R . . C7A C 0.36209(7) 1.0923(6) 0.03302(9) 0.0169(4) Uani 1 1 d . . . H7AA H 0.3608 1.1875 -0.0050 0.020 Uiso 1 1 calc R . . C8A C 0.40900(7) 1.0415(6) 0.07755(9) 0.0156(4) Uani 1 1 d . . . C9A C 0.42198(7) 1.1271(6) 0.13916(9) 0.0152(4) Uani 1 1 d . . . C10A C 0.46729(7) 1.0880(6) 0.17826(9) 0.0179(4) Uani 1 1 d . . . H10A H 0.4749 1.1490 0.2197 0.022 Uiso 1 1 calc R . . C11A C 0.50148(7) 0.9598(6) 0.15661(10) 0.0201(5) Uani 1 1 d . . . H11A H 0.5326 0.9346 0.1834 0.024 Uiso 1 1 calc R . . C12A C 0.49070(7) 0.8677(6) 0.09622(10) 0.0189(5) Uani 1 1 d . . . H12A H 0.5141 0.7786 0.0813 0.023 Uiso 1 1 calc R . . C13A C 0.44516(7) 0.9086(6) 0.05823(9) 0.0157(4) Uani 1 1 d . . . Cl1B Cl 0.393785(16) 0.99157(16) 0.33563(2) 0.02094(13) Uani 1 1 d . . . Cl2B Cl 0.126606(17) -0.00814(16) 0.29771(2) 0.02125(13) Uani 1 1 d . . . Cl3B Cl 0.070829(17) 0.20868(17) 0.05327(2) 0.02026(13) Uani 1 1 d . . . S1B S 0.312179(16) 0.68787(16) 0.24007(2) 0.01507(12) Uani 1 1 d . . . O1B O 0.22880(5) 0.3548(5) 0.15785(6) 0.0197(3) Uani 1 1 d . . . C1B C 0.33745(7) 0.8366(6) 0.31276(9) 0.0154(4) Uani 1 1 d . . . C2B C 0.30902(7) 0.8150(7) 0.34721(9) 0.0191(5) Uani 1 1 d . . . H2BA H 0.3176 0.8857 0.3883 0.023 Uiso 1 1 calc R . . C3B C 0.26496(7) 0.6731(7) 0.31344(9) 0.0181(5) Uani 1 1 d . . . H3BA H 0.2403 0.6392 0.3295 0.022 Uiso 1 1 calc R . . C4B C 0.26145(6) 0.5894(6) 0.25501(9) 0.0134(4) Uani 1 1 d . . . C5B C 0.22352(7) 0.4276(6) 0.20610(9) 0.0143(4) Uani 1 1 d . . . C6B C 0.17888(7) 0.3528(6) 0.21760(9) 0.0154(4) Uani 1 1 d . . . H6BA H 0.1749 0.4209 0.2546 0.018 Uiso 1 1 calc R . . C7B C 0.14469(7) 0.1884(6) 0.17490(9) 0.0145(4) Uani 1 1 d . . . H7BA H 0.1516 0.1286 0.1394 0.017 Uiso 1 1 calc R . . C8B C 0.09788(7) 0.0860(6) 0.17457(9) 0.0136(4) Uani 1 1 d . . . C9B C 0.08575(7) -0.0165(6) 0.22523(9) 0.0149(4) Uani 1 1 d . . . C10B C 0.04154(7) -0.1355(6) 0.22074(9) 0.0179(4) Uani 1 1 d . . . H10B H 0.0350 -0.2065 0.2560 0.021 Uiso 1 1 calc R . . C11B C 0.00688(7) -0.1506(7) 0.16458(10) 0.0198(5) Uani 1 1 d . . . H11B H -0.0235 -0.2314 0.1613 0.024 Uiso 1 1 calc R . . C12B C 0.01660(7) -0.0479(6) 0.11334(9) 0.0184(5) Uani 1 1 d . . . H12B H -0.0070 -0.0567 0.0748 0.022 Uiso 1 1 calc R . . C13B C 0.06109(7) 0.0679(6) 0.11871(9) 0.0150(4) 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 Cl1A 0.0130(2) 0.0269(3) 0.0201(2) -0.0032(2) 0.00345(17) -0.0026(2) Cl2A 0.0196(2) 0.0224(3) 0.0196(2) -0.0018(2) 0.01035(18) 0.0021(2) Cl3A 0.0248(3) 0.0238(3) 0.0184(2) -0.0035(2) 0.01108(19) -0.0013(2) S1A 0.0138(2) 0.0184(3) 0.0126(2) 0.0011(2) 0.00293(17) 0.0003(2) O1A 0.0196(7) 0.0260(9) 0.0181(7) 0.0033(7) 0.0076(6) -0.0009(7) C1A 0.0135(9) 0.0141(11) 0.0186(9) -0.0012(9) 0.0041(7) -0.0006(9) C2A 0.0181(9) 0.0194(12) 0.0162(9) 0.0006(9) 0.0082(7) -0.0011(9) C3A 0.0175(9) 0.0187(12) 0.0130(9) 0.0014(9) 0.0036(7) 0.0024(9) C4A 0.0136(9) 0.0155(11) 0.0137(8) -0.0016(9) 0.0028(7) 0.0013(9) C5A 0.0168(9) 0.0168(11) 0.0165(9) -0.0002(9) 0.0057(7) 0.0007(9) C6A 0.0165(9) 0.0194(12) 0.0166(9) 0.0019(9) 0.0036(7) -0.0002(9) C7A 0.0179(9) 0.0174(12) 0.0156(9) -0.0004(9) 0.0056(7) 0.0000(9) C8A 0.0144(9) 0.0152(11) 0.0173(9) 0.0005(9) 0.0054(7) -0.0009(9) C9A 0.0169(9) 0.0119(11) 0.0190(9) 0.0006(9) 0.0088(8) -0.0011(9) C10A 0.0192(10) 0.0163(12) 0.0171(9) 0.0005(9) 0.0045(8) -0.0027(9) C11A 0.0158(9) 0.0194(12) 0.0227(10) 0.0027(10) 0.0032(8) -0.0004(9) C12A 0.0160(9) 0.0164(12) 0.0270(10) 0.0027(10) 0.0107(8) 0.0012(9) C13A 0.0192(9) 0.0136(11) 0.0160(9) -0.0002(9) 0.0083(7) -0.0024(9) Cl1B 0.0132(2) 0.0226(3) 0.0234(2) 0.0012(2) 0.00108(18) -0.0046(2) Cl2B 0.0209(2) 0.0279(3) 0.0131(2) 0.0021(2) 0.00297(18) -0.0033(2) Cl3B 0.0175(2) 0.0294(3) 0.0124(2) 0.0008(2) 0.00305(17) -0.0017(2) S1B 0.0119(2) 0.0190(3) 0.0143(2) -0.0004(2) 0.00429(17) -0.0017(2) O1B 0.0180(7) 0.0266(9) 0.0142(6) -0.0024(7) 0.0048(5) -0.0041(7) C1B 0.0129(9) 0.0128(11) 0.0177(9) -0.0002(9) 0.0011(7) -0.0006(9) C2B 0.0186(10) 0.0222(12) 0.0155(9) -0.0022(9) 0.0041(8) -0.0004(10) C3B 0.0150(9) 0.0232(13) 0.0173(9) 0.0011(9) 0.0071(7) -0.0005(9) C4B 0.0106(8) 0.0138(11) 0.0154(9) 0.0020(9) 0.0038(7) -0.0002(8) C5B 0.0135(9) 0.0123(11) 0.0154(9) 0.0019(9) 0.0024(7) 0.0009(9) C6B 0.0141(9) 0.0158(11) 0.0161(9) 0.0001(9) 0.0050(7) 0.0001(9) C7B 0.0144(9) 0.0137(11) 0.0146(9) 0.0041(8) 0.0039(7) 0.0028(9) C8B 0.0140(9) 0.0103(10) 0.0156(9) -0.0008(8) 0.0038(7) -0.0003(8) C9B 0.0153(9) 0.0139(11) 0.0142(9) -0.0008(8) 0.0033(7) 0.0018(9) C10B 0.0200(10) 0.0165(12) 0.0200(9) 0.0019(9) 0.0105(8) 0.0003(9) C11B 0.0146(9) 0.0196(12) 0.0262(11) -0.0027(10) 0.0083(8) -0.0024(9) C12B 0.0119(9) 0.0205(12) 0.0199(9) -0.0036(10) 0.0013(7) -0.0009(9) C13B 0.0156(9) 0.0147(11) 0.0143(9) -0.0012(9) 0.0046(7) -0.0018(9) _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 Cl1A C1A 1.720(2) . ? Cl2A C9A 1.741(2) . ? Cl3A C13A 1.740(2) . ? S1A C1A 1.719(2) . ? S1A C4A 1.7324(19) . ? O1A C5A 1.230(3) . ? C1A C2A 1.361(3) . ? C2A C3A 1.413(3) . ? C2A H2AA 0.9500 . ? C3A C4A 1.374(3) . ? C3A H3AA 0.9500 . ? C4A C5A 1.464(3) . ? C5A C6A 1.488(3) . ? C6A C7A 1.336(3) . ? C6A H6AA 0.9500 . ? C7A C8A 1.473(3) . ? C7A H7AA 0.9500 . ? C8A C9A 1.403(3) . ? C8A C13A 1.411(3) . ? C9A C10A 1.385(3) . ? C10A C11A 1.385(3) . ? C10A H10A 0.9500 . ? C11A C12A 1.388(3) . ? C11A H11A 0.9500 . ? C12A C13A 1.383(3) . ? C12A H12A 0.9500 . ? Cl1B C1B 1.718(2) . ? Cl2B C9B 1.741(2) . ? Cl3B C13B 1.739(2) . ? S1B C1B 1.716(2) . ? S1B C4B 1.729(2) . ? O1B C5B 1.225(2) . ? C1B C2B 1.365(3) . ? C2B C3B 1.416(3) . ? C2B H2BA 0.9500 . ? C3B C4B 1.375(3) . ? C3B H3BA 0.9500 . ? C4B C5B 1.464(3) . ? C5B C6B 1.493(3) . ? C6B C7B 1.335(3) . ? C6B H6BA 0.9500 . ? C7B C8B 1.470(3) . ? C7B H7BA 0.9500 . ? C8B C9B 1.409(3) . ? C8B C13B 1.414(3) . ? C9B C10B 1.386(3) . ? C10B C11B 1.388(3) . ? C10B H10B 0.9500 . ? C11B C12B 1.384(3) . ? C11B H11B 0.9500 . ? C12B C13B 1.385(3) . ? C12B H12B 0.9500 . ? 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 C1A S1A C4A 90.26(10) . . ? C2A C1A S1A 113.78(15) . . ? C2A C1A Cl1A 126.53(17) . . ? S1A C1A Cl1A 119.67(12) . . ? C1A C2A C3A 111.12(19) . . ? C1A C2A H2AA 124.4 . . ? C3A C2A H2AA 124.4 . . ? C4A C3A C2A 113.26(18) . . ? C4A C3A H3AA 123.4 . . ? C2A C3A H3AA 123.4 . . ? C3A C4A C5A 131.48(18) . . ? C3A C4A S1A 111.57(15) . . ? C5A C4A S1A 116.95(15) . . ? O1A C5A C4A 120.45(18) . . ? O1A C5A C6A 122.29(19) . . ? C4A C5A C6A 117.25(18) . . ? C7A C6A C5A 118.66(19) . . ? C7A C6A H6AA 120.7 . . ? C5A C6A H6AA 120.7 . . ? C6A C7A C8A 127.07(19) . . ? C6A C7A H7AA 116.5 . . ? C8A C7A H7AA 116.5 . . ? C9A C8A C13A 115.41(18) . . ? C9A C8A C7A 125.13(19) . . ? C13A C8A C7A 119.42(18) . . ? C10A C9A C8A 122.37(19) . . ? C10A C9A Cl2A 116.48(16) . . ? C8A C9A Cl2A 121.13(15) . . ? C11A C10A C9A 119.69(19) . . ? C11A C10A H10A 120.2 . . ? C9A C10A H10A 120.2 . . ? C10A C11A C12A 120.61(19) . . ? C10A C11A H11A 119.7 . . ? C12A C11A H11A 119.7 . . ? C13A C12A C11A 118.5(2) . . ? C13A C12A H12A 120.8 . . ? C11A C12A H12A 120.8 . . ? C12A C13A C8A 123.44(19) . . ? C12A C13A Cl3A 117.74(16) . . ? C8A C13A Cl3A 118.81(15) . . ? C1B S1B C4B 90.34(10) . . ? C2B C1B S1B 113.88(15) . . ? C2B C1B Cl1B 126.48(16) . . ? S1B C1B Cl1B 119.64(12) . . ? C1B C2B C3B 110.92(19) . . ? C1B C2B H2BA 124.5 . . ? C3B C2B H2BA 124.5 . . ? C4B C3B C2B 113.12(19) . . ? C4B C3B H3BA 123.4 . . ? C2B C3B H3BA 123.4 . . ? C3B C4B C5B 131.21(19) . . ? C3B C4B S1B 111.74(15) . . ? C5B C4B S1B 117.03(15) . . ? O1B C5B C4B 120.57(18) . . ? O1B C5B C6B 121.79(18) . . ? C4B C5B C6B 117.63(17) . . ? C7B C6B C5B 118.71(18) . . ? C7B C6B H6BA 120.6 . . ? C5B C6B H6BA 120.6 . . ? C6B C7B C8B 129.64(19) . . ? C6B C7B H7BA 115.2 . . ? C8B C7B H7BA 115.2 . . ? C9B C8B C13B 114.86(18) . . ? C9B C8B C7B 126.12(17) . . ? C13B C8B C7B 118.93(18) . . ? C10B C9B C8B 122.81(18) . . ? C10B C9B Cl2B 116.06(16) . . ? C8B C9B Cl2B 121.12(15) . . ? C9B C10B C11B 119.8(2) . . ? C9B C10B H10B 120.1 . . ? C11B C10B H10B 120.1 . . ? C12B C11B C10B 119.9(2) . . ? C12B C11B H11B 120.0 . . ? C10B C11B H11B 120.0 . . ? C11B C12B C13B 119.43(19) . . ? C11B C12B H12B 120.3 . . ? C13B C12B H12B 120.3 . . ? C12B C13B C8B 123.17(19) . . ? C12B C13B Cl3B 117.51(15) . . ? C8B C13B Cl3B 119.29(15) . . ? 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 C4A S1A C1A C2A 0.7(2) . . . . ? C4A S1A C1A Cl1A -177.74(15) . . . . ? S1A C1A C2A C3A -0.9(3) . . . . ? Cl1A C1A C2A C3A 177.39(17) . . . . ? C1A C2A C3A C4A 0.7(3) . . . . ? C2A C3A C4A C5A 179.9(2) . . . . ? C2A C3A C4A S1A -0.2(3) . . . . ? C1A S1A C4A C3A -0.30(19) . . . . ? C1A S1A C4A C5A 179.60(19) . . . . ? C3A C4A C5A O1A -173.4(2) . . . . ? S1A C4A C5A O1A 6.7(3) . . . . ? C3A C4A C5A C6A 7.6(4) . . . . ? S1A C4A C5A C6A -172.27(17) . . . . ? O1A C5A C6A C7A -8.2(4) . . . . ? C4A C5A C6A C7A 170.8(2) . . . . ? C5A C6A C7A C8A -177.6(2) . . . . ? C6A C7A C8A C9A -43.5(4) . . . . ? C6A C7A C8A C13A 138.8(3) . . . . ? C13A C8A C9A C10A 0.8(3) . . . . ? C7A C8A C9A C10A -176.9(2) . . . . ? C13A C8A C9A Cl2A 178.97(17) . . . . ? C7A C8A C9A Cl2A 1.3(3) . . . . ? C8A C9A C10A C11A -0.1(4) . . . . ? Cl2A C9A C10A C11A -178.39(18) . . . . ? C9A C10A C11A C12A -0.5(4) . . . . ? C10A C11A C12A C13A 0.3(4) . . . . ? C11A C12A C13A C8A 0.4(4) . . . . ? C11A C12A C13A Cl3A -178.38(18) . . . . ? C9A C8A C13A C12A -0.9(3) . . . . ? C7A C8A C13A C12A 176.9(2) . . . . ? C9A C8A C13A Cl3A 177.85(17) . . . . ? C7A C8A C13A Cl3A -4.3(3) . . . . ? C4B S1B C1B C2B -0.2(2) . . . . ? C4B S1B C1B Cl1B 179.55(15) . . . . ? S1B C1B C2B C3B -0.1(3) . . . . ? Cl1B C1B C2B C3B -179.84(18) . . . . ? C1B C2B C3B C4B 0.5(3) . . . . ? C2B C3B C4B C5B 177.5(2) . . . . ? C2B C3B C4B S1B -0.6(3) . . . . ? C1B S1B C4B C3B 0.46(19) . . . . ? C1B S1B C4B C5B -177.93(18) . . . . ? C3B C4B C5B O1B -175.3(2) . . . . ? S1B C4B C5B O1B 2.7(3) . . . . ? C3B C4B C5B C6B 4.1(4) . . . . ? S1B C4B C5B C6B -177.88(16) . . . . ? O1B C5B C6B C7B 2.9(3) . . . . ? C4B C5B C6B C7B -176.5(2) . . . . ? C5B C6B C7B C8B -179.7(2) . . . . ? C6B C7B C8B C9B -32.7(4) . . . . ? C6B C7B C8B C13B 150.9(2) . . . . ? C13B C8B C9B C10B 1.7(3) . . . . ? C7B C8B C9B C10B -174.9(2) . . . . ? C13B C8B C9B Cl2B -179.61(17) . . . . ? C7B C8B C9B Cl2B 3.8(3) . . . . ? C8B C9B C10B C11B -1.2(4) . . . . ? Cl2B C9B C10B C11B -179.99(19) . . . . ? C9B C10B C11B C12B 0.2(4) . . . . ? C10B C11B C12B C13B 0.3(4) . . . . ? C11B C12B C13B C8B 0.3(4) . . . . ? C11B C12B C13B Cl3B -177.74(19) . . . . ? C9B C8B C13B C12B -1.2(3) . . . . ? C7B C8B C13B C12B 175.6(2) . . . . ? C9B C8B C13B Cl3B 176.77(17) . . . . ? C7B C8B C13B Cl3B -6.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.366 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.078 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 _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # C2B H2BA O1A 0.9500 2.5000 3.209(3) 131.00 4_586 yes #========================================================================== #End of cif