# Cyclopentadithiophene Based Organic Semiconductors: Effect of Fluorinated # Substituents on Electrochemical and Charge Transport Properties # J. Sreedhar Reddy, Tejaswini Kale, Balaji Ganapathy, A. Chandrasekaran, # S. Thayumanavan* # Department of Chemistry, University of Massachusetts, Amherst, MA 01003, USA #Compound 1 data_js14 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H16 O2 S2' _chemical_formula_weight 388.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 5.96860(10) _cell_length_b 13.7161(4) _cell_length_c 22.6208(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1851.87(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour Yellow _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.303 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2893 _diffrn_reflns_av_R_equivalents 0.0135 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 4.14 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1616 _reflns_number_gt 1279 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Molecule posseses a 2-fold symmetry parallel to the z-axis. ; _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^)+(0.0553P)^2^+0.7613P] 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 1616 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1212 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 S1 S -0.00060(11) 0.15222(5) 0.43045(2) 0.0672(3) Uani 1 1 d . . . O1 O 0.1371(3) 0.31681(14) 0.24357(6) 0.0832(6) Uani 1 1 d . . . C1 C 0.1560(4) 0.21619(17) 0.38084(9) 0.0617(6) Uani 1 1 d . . . C2 C 0.0953(4) 0.19589(18) 0.32377(9) 0.0624(6) Uani 1 1 d . . . C3 C -0.0788(5) 0.12845(18) 0.31968(10) 0.0672(7) Uani 1 1 d . . . H3 H -0.1392 0.1074 0.2840 0.081 Uiso 1 1 calc R . . C4 C -0.1518(4) 0.09633(18) 0.37388(9) 0.0629(6) Uani 1 1 d . . . C5 C 0.2500 0.2500 0.28140(13) 0.0684(9) Uani 1 2 d S . . C6 C 0.1537(5) 0.2842(2) 0.18706(10) 0.0848(9) Uani 1 1 d . . . H6A H 0.1805 0.3380 0.1601 0.102 Uiso 1 1 calc R . . H6B H 0.0173 0.2510 0.1752 0.102 Uiso 1 1 calc R . . C7 C -0.3250(4) 0.02439(17) 0.38740(10) 0.0645(6) Uani 1 1 d . . . C8 C -0.5073(5) 0.0118(2) 0.34959(13) 0.0776(8) Uani 1 1 d . . . H8 H -0.5176 0.0497 0.3156 0.093 Uiso 1 1 calc R . . C9 C -0.6716(5) -0.0552(2) 0.36151(14) 0.0849(8) Uani 1 1 d . . . H9 H -0.7914 -0.0624 0.3356 0.102 Uiso 1 1 calc R . . C10 C -0.6600(5) -0.1122(2) 0.41202(14) 0.0849(8) Uani 1 1 d . . . H10 H -0.7725 -0.1570 0.4205 0.102 Uiso 1 1 calc R . . C11 C -0.4805(6) -0.1017(2) 0.44928(13) 0.0872(9) Uani 1 1 d . . . H11 H -0.4706 -0.1405 0.4829 0.105 Uiso 1 1 calc R . . C12 C -0.3145(5) -0.03452(19) 0.43749(11) 0.0751(7) Uani 1 1 d . . . H12 H -0.1941 -0.0284 0.4633 0.090 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0825(5) 0.0744(5) 0.0446(4) -0.0010(2) -0.0012(3) 0.0003(3) O1 0.1177(15) 0.0864(11) 0.0456(9) 0.0043(8) -0.0029(9) 0.0460(11) C1 0.0723(15) 0.0677(14) 0.0452(11) -0.0010(10) -0.0018(10) 0.0125(11) C2 0.0755(15) 0.0667(14) 0.0451(12) -0.0006(10) -0.0055(11) 0.0171(13) C3 0.0796(16) 0.0707(15) 0.0511(13) -0.0061(11) -0.0132(12) 0.0169(14) C4 0.0727(15) 0.0638(13) 0.0523(12) -0.0031(11) -0.0093(11) 0.0133(12) C5 0.090(2) 0.071(2) 0.0446(16) 0.000 0.000 0.031(2) C6 0.121(2) 0.0824(18) 0.0513(13) 0.0001(12) -0.0161(14) 0.0182(16) C7 0.0761(16) 0.0582(13) 0.0592(13) -0.0060(11) -0.0042(11) 0.0132(12) C8 0.0859(18) 0.0660(16) 0.0809(18) 0.0016(13) -0.0141(14) 0.0127(15) C9 0.087(2) 0.0696(16) 0.099(2) -0.0079(15) -0.0145(16) 0.0079(16) C10 0.089(2) 0.0664(17) 0.099(2) -0.0129(16) 0.0080(17) -0.0010(15) C11 0.117(3) 0.0740(18) 0.0701(16) -0.0007(14) 0.0046(16) -0.0011(17) C12 0.091(2) 0.0747(16) 0.0591(14) -0.0048(12) -0.0054(13) 0.0040(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.704(2) . ? S1 C4 1.743(2) . ? O1 C6 1.358(3) . ? O1 C5 1.423(2) . ? C1 C2 1.369(3) . ? C1 C1 1.456(5) 2 ? C2 C3 1.394(4) . ? C2 C5 1.524(3) . ? C3 C4 1.374(3) . ? C3 H3 0.9300 . ? C4 C7 1.461(3) . ? C5 C2 1.524(3) 2 ? C6 C6 1.484(5) 2 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C12 1.393(3) . ? C7 C8 1.395(4) . ? C8 C9 1.371(4) . ? C8 H8 0.9300 . ? C9 C10 1.386(4) . ? C9 H9 0.9300 . ? C10 C11 1.370(4) . ? C10 H10 0.9300 . ? C11 C12 1.380(4) . ? C11 H11 0.9300 . ? C12 H12 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 91.55(12) . . ? C6 O1 C5 108.63(18) . . ? C2 C1 C1 109.49(15) . 2 ? C2 C1 S1 111.76(19) . . ? C1 C1 S1 138.68(8) 2 . ? C1 C2 C3 113.3(2) . . ? C1 C2 C5 109.5(2) . . ? C3 C2 C5 137.13(19) . . ? C4 C3 C2 112.9(2) . . ? C4 C3 H3 123.5 . . ? C2 C3 H3 123.5 . . ? C3 C4 C7 128.9(2) . . ? C3 C4 S1 110.5(2) . . ? C7 C4 S1 120.62(17) . . ? O1 C5 O1 106.1(2) 2 . ? O1 C5 C2 110.58(12) . 2 ? O1 C5 C2 113.87(12) . . ? C2 C5 C2 102.1(2) 2 . ? O1 C6 C6 105.35(15) . 2 ? O1 C6 H6A 110.7 . . ? C6 C6 H6A 110.7 2 . ? O1 C6 H6B 110.7 . . ? C6 C6 H6B 110.7 2 . ? H6A C6 H6B 108.8 . . ? C12 C7 C8 117.5(3) . . ? C12 C7 C4 122.0(2) . . ? C8 C7 C4 120.5(2) . . ? C9 C8 C7 121.3(3) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C10 120.3(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 119.1(3) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 120.8(3) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C7 120.8(3) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? 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 0.10(18) . . . . ? C4 S1 C1 C1 -176.5(4) . . . 2 ? C1 C1 C2 C3 177.7(2) 2 . . . ? S1 C1 C2 C3 0.1(3) . . . . ? C1 C1 C2 C5 1.1(3) 2 . . . ? S1 C1 C2 C5 -176.46(12) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C5 C2 C3 C4 174.9(2) . . . . ? C2 C3 C4 C7 -178.1(2) . . . . ? C2 C3 C4 S1 0.4(3) . . . . ? C1 S1 C4 C3 -0.27(18) . . . . ? C1 S1 C4 C7 178.37(19) . . . . ? C6 O1 C5 O1 8.27(16) . . . 2 ? C6 O1 C5 C2 132.2(2) . . . 2 ? C6 O1 C5 C2 -113.6(2) . . . . ? C1 C2 C5 O1 121.0(2) . . . 2 ? C3 C2 C5 O1 -54.3(3) . . . 2 ? C1 C2 C5 O1 -119.6(2) . . . . ? C3 C2 C5 O1 65.1(3) . . . . ? C1 C2 C5 C2 -0.45(12) . . . 2 ? C3 C2 C5 C2 -175.8(3) . . . 2 ? C5 O1 C6 C6 -20.0(4) . . . 2 ? C3 C4 C7 C12 148.9(3) . . . . ? S1 C4 C7 C12 -29.5(3) . . . . ? C3 C4 C7 C8 -30.4(4) . . . . ? S1 C4 C7 C8 151.2(2) . . . . ? C12 C7 C8 C9 0.7(4) . . . . ? C4 C7 C8 C9 -179.9(2) . . . . ? C7 C8 C9 C10 0.2(4) . . . . ? C8 C9 C10 C11 -1.0(4) . . . . ? C9 C10 C11 C12 1.0(4) . . . . ? C10 C11 C12 C7 -0.1(4) . . . . ? C8 C7 C12 C11 -0.8(4) . . . . ? C4 C7 C12 C11 179.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.198 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.033 #===END #Compound 2 data_js3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H12 O S2' _chemical_formula_weight 344.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 16.9741(4) _cell_length_b 6.4960(2) _cell_length_c 7.1152(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.0088(13) _cell_angle_gamma 90.00 _cell_volume 784.43(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour 'brownish-yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.343 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2522 _diffrn_reflns_av_R_equivalents 0.0120 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.78 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1381 _reflns_number_gt 1279 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.3276P] 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 1381 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0786 _refine_ls_wR_factor_gt 0.0769 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 S1 S 0.61614(2) 0.14382(6) 0.18375(6) 0.03557(17) Uani 1 1 d . . . O1 O 0.5000 0.8403(2) 0.2500 0.0511(5) Uani 1 2 d S . . C1 C 0.54207(8) 0.3129(2) 0.2253(2) 0.0291(3) Uani 1 1 d . . . C2 C 0.56712(8) 0.5132(2) 0.2106(2) 0.0299(3) Uani 1 1 d . . . C3 C 0.64732(8) 0.5324(2) 0.1652(2) 0.0324(3) Uani 1 1 d . . . H3 H 0.6732 0.6575 0.1507 0.039 Uiso 1 1 calc R . . C4 C 0.68233(8) 0.3439(2) 0.1450(2) 0.0305(3) Uani 1 1 d . . . C5 C 0.5000 0.6539(3) 0.2500 0.0318(5) Uani 1 2 d S . . C6 C 0.76440(8) 0.2966(2) 0.09626(19) 0.0309(3) Uani 1 1 d . . . C7 C 0.82421(9) 0.4371(3) 0.1394(2) 0.0380(4) Uani 1 1 d . . . H7 H 0.8123 0.5601 0.1993 0.046 Uiso 1 1 calc R . . C8 C 0.90125(10) 0.3937(3) 0.0931(3) 0.0456(4) Uani 1 1 d . . . H8 H 0.9408 0.4883 0.1222 0.055 Uiso 1 1 calc R . . C9 C 0.92013(9) 0.2124(3) 0.0045(3) 0.0469(4) Uani 1 1 d . . . H9 H 0.9721 0.1848 -0.0263 0.056 Uiso 1 1 calc R . . C10 C 0.86191(10) 0.0722(3) -0.0382(2) 0.0456(4) Uani 1 1 d . . . H10 H 0.8745 -0.0507 -0.0975 0.055 Uiso 1 1 calc R . . C11 C 0.78437(9) 0.1138(3) 0.0069(2) 0.0388(4) Uani 1 1 d . . . H11 H 0.7453 0.0184 -0.0229 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0227(2) 0.0285(2) 0.0558(3) -0.00014(16) 0.00557(17) 0.00070(14) O1 0.0361(9) 0.0254(9) 0.0921(14) 0.000 0.0125(9) 0.000 C1 0.0209(7) 0.0300(8) 0.0364(8) -0.0002(6) 0.0012(6) 0.0007(6) C2 0.0245(7) 0.0293(8) 0.0359(7) 0.0007(6) 0.0018(6) 0.0001(6) C3 0.0265(7) 0.0307(8) 0.0400(8) 0.0018(6) 0.0028(6) -0.0037(6) C4 0.0230(7) 0.0338(8) 0.0349(8) 0.0009(6) 0.0026(6) -0.0021(6) C5 0.0257(10) 0.0307(12) 0.0392(11) 0.000 0.0025(8) 0.000 C6 0.0227(7) 0.0368(8) 0.0334(7) 0.0021(6) 0.0023(6) 0.0007(6) C7 0.0293(8) 0.0403(9) 0.0445(9) -0.0044(7) 0.0043(6) -0.0030(7) C8 0.0257(8) 0.0544(11) 0.0568(10) -0.0002(9) 0.0034(7) -0.0071(7) C9 0.0254(8) 0.0577(11) 0.0579(10) 0.0046(9) 0.0096(7) 0.0078(8) C10 0.0371(9) 0.0468(10) 0.0533(10) -0.0053(8) 0.0081(7) 0.0094(8) C11 0.0294(8) 0.0402(9) 0.0470(9) -0.0046(7) 0.0020(7) -0.0014(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.6995(14) . ? S1 C4 1.7429(14) . ? O1 C5 1.211(3) . ? C1 C2 1.373(2) . ? C1 C1 1.477(3) 2_655 ? C2 C3 1.4103(19) . ? C2 C5 1.4911(19) . ? C3 C4 1.370(2) . ? C3 H3 0.9300 . ? C4 C6 1.4738(19) . ? C5 C2 1.4911(19) 2_655 ? C6 C11 1.392(2) . ? C6 C7 1.395(2) . ? C7 C8 1.383(2) . ? C7 H7 0.9300 . ? C8 C9 1.377(3) . ? C8 H8 0.9300 . ? C9 C10 1.374(3) . ? C9 H9 0.9300 . ? C10 C11 1.387(2) . ? C10 H10 0.9300 . ? C11 H11 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 91.51(7) . . ? C2 C1 C1 108.67(8) . 2_655 ? C2 C1 S1 111.60(10) . . ? C1 C1 S1 139.72(5) 2_655 . ? C1 C2 C3 113.76(13) . . ? C1 C2 C5 109.14(12) . . ? C3 C2 C5 137.09(13) . . ? C4 C3 C2 111.52(13) . . ? C4 C3 H3 124.2 . . ? C2 C3 H3 124.2 . . ? C3 C4 C6 128.63(13) . . ? C3 C4 S1 111.60(11) . . ? C6 C4 S1 119.77(11) . . ? O1 C5 C2 127.82(8) . 2_655 ? O1 C5 C2 127.82(8) . . ? C2 C5 C2 104.37(17) 2_655 . ? C11 C6 C7 118.44(13) . . ? C11 C6 C4 121.60(14) . . ? C7 C6 C4 119.96(14) . . ? C8 C7 C6 120.15(16) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C7 120.78(16) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C10 C9 C8 119.75(15) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 120.11(17) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C6 120.77(15) . . ? C10 C11 H11 119.6 . . ? C6 C11 H11 119.6 . . ? 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 -0.15(12) . . . . ? C4 S1 C1 C1 -179.5(2) . . . 2_655 ? C1 C1 C2 C3 179.52(14) 2_655 . . . ? S1 C1 C2 C3 -0.04(17) . . . . ? C1 C1 C2 C5 0.02(19) 2_655 . . . ? S1 C1 C2 C5 -179.54(8) . . . . ? C1 C2 C3 C4 0.27(19) . . . . ? C5 C2 C3 C4 179.58(14) . . . . ? C2 C3 C4 C6 179.26(14) . . . . ? C2 C3 C4 S1 -0.38(17) . . . . ? C1 S1 C4 C3 0.31(12) . . . . ? C1 S1 C4 C6 -179.36(12) . . . . ? C1 C2 C5 O1 179.99(8) . . . . ? C3 C2 C5 O1 0.7(2) . . . . ? C1 C2 C5 C2 -0.01(8) . . . 2_655 ? C3 C2 C5 C2 -179.3(2) . . . 2_655 ? C3 C4 C6 C11 -153.07(17) . . . . ? S1 C4 C6 C11 26.54(19) . . . . ? C3 C4 C6 C7 26.8(2) . . . . ? S1 C4 C6 C7 -153.59(13) . . . . ? C11 C6 C7 C8 0.2(2) . . . . ? C4 C6 C7 C8 -179.71(15) . . . . ? C6 C7 C8 C9 -0.1(3) . . . . ? C7 C8 C9 C10 -0.2(3) . . . . ? C8 C9 C10 C11 0.3(3) . . . . ? C9 C10 C11 C6 -0.2(3) . . . . ? C7 C6 C11 C10 0.0(2) . . . . ? C4 C6 C11 C10 179.86(15) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.296 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.035 #===END #Compound 3 data_js9 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H12 N2 S2' _chemical_formula_weight 392.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 14.8678(4) _cell_length_b 7.52970(10) _cell_length_c 16.9934(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.7169(12) _cell_angle_gamma 90.00 _cell_volume 1892.95(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour 'dark-blue' _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.293 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6105 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 25.14 _reflns_number_total 3328 _reflns_number_gt 2639 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+0.5444P] 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 3328 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0933 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 S1 S 0.58010(3) 0.20289(7) 0.90765(3) 0.04208(16) Uani 1 1 d . . . S2 S 0.33531(3) 0.42416(7) 0.84378(3) 0.04542(16) Uani 1 1 d . . . N1 N 0.50653(14) 0.1602(3) 1.24413(11) 0.0663(5) Uani 1 1 d . . . N2 N 0.25007(17) 0.4421(4) 1.18388(14) 0.0962(8) Uani 1 1 d . . . C1 C 0.63273(12) 0.1368(2) 0.99909(11) 0.0394(4) Uani 1 1 d . . . C2 C 0.57918(12) 0.1690(2) 1.05832(11) 0.0390(4) Uani 1 1 d . . . H2 H 0.5959 0.1430 1.1113 0.047 Uiso 1 1 calc R . . C3 C 0.49553(12) 0.2464(2) 1.03008(10) 0.0371(4) Uani 1 1 d . . . C4 C 0.48697(12) 0.2727(2) 0.94916(10) 0.0371(4) Uani 1 1 d . . . C5 C 0.39906(12) 0.3542(2) 0.92637(10) 0.0377(4) Uani 1 1 d . . . C6 C 0.35484(12) 0.3794(2) 0.99317(11) 0.0379(4) Uani 1 1 d . . . C7 C 0.26852(13) 0.4562(2) 0.97711(11) 0.0417(5) Uani 1 1 d . . . H7 H 0.2303 0.4818 1.0157 0.050 Uiso 1 1 calc R . . C8 C 0.24745(13) 0.4889(3) 0.89823(11) 0.0428(5) Uani 1 1 d . . . C9 C 0.41340(12) 0.3126(2) 1.06155(11) 0.0379(4) Uani 1 1 d . . . C10 C 0.39591(13) 0.3103(3) 1.13829(11) 0.0426(5) Uani 1 1 d . . . C11 C 0.45782(14) 0.2306(3) 1.19810(12) 0.0473(5) Uani 1 1 d . . . C12 C 0.31476(17) 0.3843(3) 1.16402(13) 0.0585(6) Uani 1 1 d . . . C13 C 0.72412(13) 0.0598(2) 1.00534(12) 0.0439(5) Uani 1 1 d . . . C14 C 0.76660(15) 0.0061(3) 1.07758(13) 0.0538(5) Uani 1 1 d . . . H14 H 0.7371 0.0199 1.1229 0.065 Uiso 1 1 calc R . . C15 C 0.85203(16) -0.0676(3) 1.08350(17) 0.0661(7) Uani 1 1 d . . . H15 H 0.8794 -0.1027 1.1326 0.079 Uiso 1 1 calc R . . C16 C 0.89674(17) -0.0894(3) 1.01732(19) 0.0728(8) Uani 1 1 d . . . H16 H 0.9541 -0.1401 1.0213 0.087 Uiso 1 1 calc R . . C17 C 0.85665(17) -0.0364(4) 0.94597(18) 0.0773(8) Uani 1 1 d . . . H17 H 0.8869 -0.0504 0.9010 0.093 Uiso 1 1 calc R . . C18 C 0.77090(16) 0.0383(3) 0.93941(15) 0.0641(6) Uani 1 1 d . . . H18 H 0.7445 0.0745 0.8901 0.077 Uiso 1 1 calc R . . C19 C 0.16438(14) 0.5659(2) 0.85818(12) 0.0456(5) Uani 1 1 d . . . C20 C 0.16431(16) 0.6522(3) 0.78603(13) 0.0624(6) Uani 1 1 d . . . H20 H 0.2174 0.6597 0.7616 0.075 Uiso 1 1 calc R . . C21 C 0.0852(2) 0.7274(4) 0.75006(16) 0.0779(8) Uani 1 1 d . . . H21 H 0.0859 0.7847 0.7016 0.093 Uiso 1 1 calc R . . C22 C 0.00692(19) 0.7180(4) 0.78504(17) 0.0776(8) Uani 1 1 d . . . H22 H -0.0455 0.7698 0.7608 0.093 Uiso 1 1 calc R . . C23 C 0.00525(17) 0.6319(3) 0.85626(17) 0.0708(7) Uani 1 1 d . . . H23 H -0.0483 0.6244 0.8800 0.085 Uiso 1 1 calc R . . C24 C 0.08367(15) 0.5563(3) 0.89243(14) 0.0587(6) Uani 1 1 d . . . H24 H 0.0822 0.4981 0.9406 0.070 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0443(3) 0.0461(3) 0.0361(3) -0.0008(2) 0.0055(2) 0.0002(2) S2 0.0472(3) 0.0531(3) 0.0350(3) -0.0007(2) -0.0006(2) 0.0030(2) N1 0.0756(14) 0.0820(14) 0.0395(10) 0.0038(10) -0.0033(10) 0.0032(11) N2 0.0757(16) 0.141(2) 0.0759(16) -0.0036(15) 0.0263(13) 0.0298(16) C1 0.0418(11) 0.0362(10) 0.0398(11) 0.0003(8) 0.0019(9) -0.0046(8) C2 0.0423(11) 0.0390(10) 0.0349(10) 0.0013(8) 0.0002(8) -0.0044(8) C3 0.0410(11) 0.0356(10) 0.0345(10) -0.0014(8) 0.0038(8) -0.0058(8) C4 0.0405(11) 0.0367(10) 0.0340(10) -0.0029(8) 0.0028(8) -0.0042(8) C5 0.0408(11) 0.0375(10) 0.0343(10) -0.0015(8) 0.0007(8) -0.0041(8) C6 0.0397(11) 0.0382(10) 0.0355(10) -0.0020(8) 0.0023(8) -0.0040(8) C7 0.0416(11) 0.0423(11) 0.0417(11) -0.0035(9) 0.0070(9) -0.0031(8) C8 0.0431(11) 0.0407(10) 0.0438(11) -0.0037(9) -0.0001(9) -0.0027(8) C9 0.0413(11) 0.0355(10) 0.0367(10) -0.0015(8) 0.0029(8) -0.0069(8) C10 0.0448(11) 0.0462(11) 0.0371(11) -0.0015(9) 0.0057(9) -0.0019(9) C11 0.0527(13) 0.0570(13) 0.0329(11) -0.0022(10) 0.0087(10) -0.0047(10) C12 0.0592(15) 0.0763(16) 0.0408(12) 0.0029(11) 0.0092(11) 0.0036(12) C13 0.0423(11) 0.0370(10) 0.0518(12) -0.0003(9) 0.0020(9) -0.0041(8) C14 0.0530(13) 0.0487(12) 0.0581(13) -0.0006(10) -0.0029(11) 0.0017(10) C15 0.0540(15) 0.0538(13) 0.0861(18) 0.0080(13) -0.0149(13) 0.0020(11) C16 0.0445(14) 0.0593(15) 0.114(2) 0.0115(15) 0.0069(15) 0.0043(11) C17 0.0573(16) 0.0849(19) 0.094(2) 0.0116(16) 0.0266(15) 0.0152(14) C18 0.0550(15) 0.0748(16) 0.0643(15) 0.0096(12) 0.0144(12) 0.0120(12) C19 0.0453(12) 0.0406(11) 0.0489(12) -0.0065(9) -0.0053(9) 0.0030(9) C20 0.0647(15) 0.0679(15) 0.0528(14) 0.0005(12) -0.0036(11) 0.0101(12) C21 0.091(2) 0.0782(18) 0.0592(16) 0.0019(13) -0.0173(15) 0.0265(15) C22 0.0683(18) 0.0729(17) 0.085(2) -0.0176(15) -0.0269(15) 0.0266(14) C23 0.0543(15) 0.0681(16) 0.0877(19) -0.0118(14) -0.0036(13) 0.0123(12) C24 0.0514(14) 0.0567(14) 0.0661(14) -0.0004(11) -0.0035(11) 0.0054(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 S1 C4 1.6985(19) . ? S1 C1 1.7413(19) . ? S2 C5 1.6972(18) . ? S2 C8 1.744(2) . ? N1 C11 1.142(3) . ? N2 C12 1.137(3) . ? C1 C2 1.366(3) . ? C1 C13 1.471(3) . ? C2 C3 1.413(3) . ? C2 H2 0.9300 . ? C3 C4 1.383(2) . ? C3 C9 1.468(3) . ? C4 C5 1.461(3) . ? C5 C6 1.381(3) . ? C6 C7 1.409(3) . ? C6 C9 1.470(3) . ? C7 C8 1.368(3) . ? C7 H7 0.9300 . ? C8 C19 1.469(3) . ? C9 C10 1.355(3) . ? C10 C11 1.433(3) . ? C10 C12 1.436(3) . ? C13 C14 1.384(3) . ? C13 C18 1.386(3) . ? C14 C15 1.381(3) . ? C14 H14 0.9300 . ? C15 C16 1.372(4) . ? C15 H15 0.9300 . ? C16 C17 1.356(4) . ? C16 H16 0.9300 . ? C17 C18 1.388(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C24 1.387(3) . ? C19 C20 1.388(3) . ? C20 C21 1.390(3) . ? C20 H20 0.9300 . ? C21 C22 1.361(4) . ? C21 H21 0.9300 . ? C22 C23 1.375(4) . ? C22 H22 0.9300 . ? C23 C24 1.385(3) . ? C23 H23 0.9300 . ? C24 H24 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 C4 S1 C1 91.73(9) . . ? C5 S2 C8 91.95(9) . . ? C2 C1 C13 128.22(18) . . ? C2 C1 S1 111.34(14) . . ? C13 C1 S1 120.43(14) . . ? C1 C2 C3 112.38(17) . . ? C1 C2 H2 123.8 . . ? C3 C2 H2 123.8 . . ? C4 C3 C2 112.79(17) . . ? C4 C3 C9 108.44(16) . . ? C2 C3 C9 138.75(17) . . ? C3 C4 C5 108.36(16) . . ? C3 C4 S1 111.76(14) . . ? C5 C4 S1 139.88(14) . . ? C6 C5 C4 109.06(16) . . ? C6 C5 S2 111.40(14) . . ? C4 C5 S2 139.53(14) . . ? C5 C6 C7 113.34(17) . . ? C5 C6 C9 108.06(16) . . ? C7 C6 C9 138.59(17) . . ? C8 C7 C6 112.26(18) . . ? C8 C7 H7 123.9 . . ? C6 C7 H7 123.9 . . ? C7 C8 C19 128.67(19) . . ? C7 C8 S2 111.05(15) . . ? C19 C8 S2 120.28(15) . . ? C10 C9 C3 126.33(17) . . ? C10 C9 C6 127.59(17) . . ? C3 C9 C6 106.08(15) . . ? C9 C10 C11 121.12(18) . . ? C9 C10 C12 122.37(18) . . ? C11 C10 C12 116.51(17) . . ? N1 C11 C10 177.0(2) . . ? N2 C12 C10 179.4(3) . . ? C14 C13 C18 117.5(2) . . ? C14 C13 C1 121.04(18) . . ? C18 C13 C1 121.47(19) . . ? C15 C14 C13 121.2(2) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C16 C15 C14 120.4(2) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 119.5(2) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C18 120.6(2) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C13 C18 C17 120.9(2) . . ? C13 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C24 C19 C20 118.1(2) . . ? C24 C19 C8 120.53(19) . . ? C20 C19 C8 121.4(2) . . ? C19 C20 C21 120.4(2) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C22 C21 C20 120.6(3) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 C23 120.0(2) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C22 C23 C24 119.7(3) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C23 C24 C19 121.2(2) . . ? C23 C24 H24 119.4 . . ? C19 C24 H24 119.4 . . ? 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 -0.08(15) . . . . ? C4 S1 C1 C13 -179.27(16) . . . . ? C13 C1 C2 C3 179.31(17) . . . . ? S1 C1 C2 C3 0.2(2) . . . . ? C1 C2 C3 C4 -0.2(2) . . . . ? C1 C2 C3 C9 -178.6(2) . . . . ? C2 C3 C4 C5 -179.49(15) . . . . ? C9 C3 C4 C5 -0.6(2) . . . . ? C2 C3 C4 S1 0.2(2) . . . . ? C9 C3 C4 S1 179.04(12) . . . . ? C1 S1 C4 C3 -0.06(15) . . . . ? C1 S1 C4 C5 179.5(2) . . . . ? C3 C4 C5 C6 0.7(2) . . . . ? S1 C4 C5 C6 -178.81(17) . . . . ? C3 C4 C5 S2 -178.40(17) . . . . ? S1 C4 C5 S2 2.1(4) . . . . ? C8 S2 C5 C6 -0.02(15) . . . . ? C8 S2 C5 C4 179.1(2) . . . . ? C4 C5 C6 C7 -179.41(15) . . . . ? S2 C5 C6 C7 0.0(2) . . . . ? C4 C5 C6 C9 -0.5(2) . . . . ? S2 C5 C6 C9 178.89(12) . . . . ? C5 C6 C7 C8 0.1(2) . . . . ? C9 C6 C7 C8 -178.4(2) . . . . ? C6 C7 C8 C19 179.48(18) . . . . ? C6 C7 C8 S2 -0.1(2) . . . . ? C5 S2 C8 C7 0.06(15) . . . . ? C5 S2 C8 C19 -179.55(16) . . . . ? C4 C3 C9 C10 179.89(18) . . . . ? C2 C3 C9 C10 -1.7(3) . . . . ? C4 C3 C9 C6 0.33(19) . . . . ? C2 C3 C9 C6 178.7(2) . . . . ? C5 C6 C9 C10 -179.44(18) . . . . ? C7 C6 C9 C10 -0.9(4) . . . . ? C5 C6 C9 C3 0.1(2) . . . . ? C7 C6 C9 C3 178.6(2) . . . . ? C3 C9 C10 C11 -3.2(3) . . . . ? C6 C9 C10 C11 176.21(18) . . . . ? C3 C9 C10 C12 177.62(19) . . . . ? C6 C9 C10 C12 -2.9(3) . . . . ? C2 C1 C13 C14 1.2(3) . . . . ? S1 C1 C13 C14 -179.74(15) . . . . ? C2 C1 C13 C18 -178.8(2) . . . . ? S1 C1 C13 C18 0.3(3) . . . . ? C18 C13 C14 C15 -0.6(3) . . . . ? C1 C13 C14 C15 179.42(19) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C17 0.6(4) . . . . ? C15 C16 C17 C18 -0.4(4) . . . . ? C14 C13 C18 C17 0.8(3) . . . . ? C1 C13 C18 C17 -179.2(2) . . . . ? C16 C17 C18 C13 -0.3(4) . . . . ? C7 C8 C19 C24 -23.9(3) . . . . ? S2 C8 C19 C24 155.59(17) . . . . ? C7 C8 C19 C20 155.1(2) . . . . ? S2 C8 C19 C20 -25.4(3) . . . . ? C24 C19 C20 C21 0.4(3) . . . . ? C8 C19 C20 C21 -178.6(2) . . . . ? C19 C20 C21 C22 0.2(4) . . . . ? C20 C21 C22 C23 -0.7(4) . . . . ? C21 C22 C23 C24 0.6(4) . . . . ? C22 C23 C24 C19 0.1(4) . . . . ? C20 C19 C24 C23 -0.6(3) . . . . ? C8 C19 C24 C23 178.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.177 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.038 #===END #Compound 4 data_js7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H6 F10 O2 S2' _chemical_formula_weight 568.40 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8519(2) _cell_length_b 9.6987(2) _cell_length_c 13.1288(3) _cell_angle_alpha 70.3916(10) _cell_angle_beta 78.2754(13) _cell_angle_gamma 82.4345(13) _cell_volume 1037.15(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.006 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.820 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.369 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6596 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.25 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3649 _reflns_number_gt 3117 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+3.5822P] 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 3649 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0660 _refine_ls_wR_factor_ref 0.1919 _refine_ls_wR_factor_gt 0.1880 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.137 _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 S1 S 0.08283(16) 0.76725(14) 0.42793(11) 0.0534(4) Uani 1 1 d . . . S2 S 0.25273(16) 0.94719(15) 0.60996(12) 0.0542(4) Uani 1 1 d . . . F1 F -0.1018(5) 0.5731(4) 0.4155(3) 0.0813(11) Uani 1 1 d . . . F2 F -0.2289(5) 0.4157(4) 0.3290(3) 0.0917(13) Uani 1 1 d . . . F3 F -0.2034(5) 0.4859(5) 0.1080(4) 0.0962(13) Uani 1 1 d . . . F4 F -0.0342(6) 0.7153(5) -0.0250(3) 0.1015(14) Uani 1 1 d . . . F5 F 0.1014(5) 0.8683(4) 0.0574(3) 0.0869(12) Uani 1 1 d . . . F6 F 0.5388(4) 1.3432(4) 0.5283(3) 0.0693(9) Uani 1 1 d . . . F7 F 0.6232(5) 1.4297(4) 0.6779(3) 0.0799(11) Uani 1 1 d . . . F8 F 0.5369(5) 1.2872(5) 0.8950(3) 0.0917(12) Uani 1 1 d . . . F9 F 0.3516(5) 1.0583(5) 0.9584(3) 0.0902(12) Uani 1 1 d . . . F10 F 0.2604(4) 0.9728(4) 0.8111(3) 0.0719(10) Uani 1 1 d . . . O1 O 0.4069(5) 1.1607(4) 0.2188(3) 0.0662(11) Uani 1 1 d . . . O2 O 0.1737(5) 1.2805(4) 0.2526(4) 0.0721(12) Uani 1 1 d . . . C1 C 0.0734(6) 0.8220(6) 0.2879(4) 0.0517(12) Uani 1 1 d . . . C2 C 0.1354(6) 0.9566(6) 0.2335(5) 0.0553(13) Uani 1 1 d . . . H2 H 0.1410 1.0045 0.1586 0.066 Uiso 1 1 calc R . . C3 C 0.1879(6) 1.0114(5) 0.3037(4) 0.0514(12) Uani 1 1 d . . . C4 C 0.1695(6) 0.9215(5) 0.4098(4) 0.0496(12) Uani 1 1 d . . . C5 C 0.2307(6) 0.9874(5) 0.4770(4) 0.0498(12) Uani 1 1 d . . . C6 C 0.2870(6) 1.1195(6) 0.4107(4) 0.0510(12) Uani 1 1 d . . . C7 C 0.3479(6) 1.1911(6) 0.4681(5) 0.0546(13) Uani 1 1 d . . . H7 H 0.3886 1.2825 0.4359 0.065 Uiso 1 1 calc R . . C8 C 0.3412(6) 1.1115(5) 0.5775(4) 0.0500(12) Uani 1 1 d . . . C9 C 0.2654(6) 1.1479(5) 0.2937(5) 0.0536(13) Uani 1 1 d . . . C10 C 0.0061(6) 0.7313(6) 0.2414(4) 0.0519(13) Uani 1 1 d . . . C11 C -0.0781(7) 0.6099(6) 0.3047(5) 0.0560(13) Uani 1 1 d . . . C12 C -0.1454(7) 0.5286(6) 0.2612(5) 0.0643(15) Uani 1 1 d . . . C13 C -0.1318(8) 0.5622(7) 0.1505(6) 0.0670(16) Uani 1 1 d . . . C14 C -0.0502(8) 0.6779(8) 0.0843(5) 0.0693(16) Uani 1 1 d . . . C15 C 0.0200(7) 0.7588(6) 0.1285(5) 0.0596(14) Uani 1 1 d . . . C16 C 0.3929(6) 1.1538(5) 0.6620(4) 0.0501(12) Uani 1 1 d . . . C17 C 0.4870(6) 1.2691(6) 0.6341(5) 0.0566(14) Uani 1 1 d . . . C18 C 0.5349(7) 1.3141(6) 0.7102(5) 0.0604(14) Uani 1 1 d . . . C19 C 0.4909(7) 1.2449(7) 0.8192(6) 0.0676(16) Uani 1 1 d . . . C20 C 0.3989(7) 1.1267(7) 0.8530(5) 0.0622(15) Uani 1 1 d . . . C21 C 0.3521(6) 1.0845(6) 0.7736(5) 0.0557(13) Uani 1 1 d . . . C22 C 0.4278(10) 1.3112(7) 0.1711(6) 0.089(2) Uani 1 1 d . . . H22A H 0.4830 1.3326 0.0963 0.107 Uiso 1 1 calc R . . H22B H 0.4854 1.3444 0.2129 0.107 Uiso 1 1 calc R . . C23 C 0.2691(9) 1.3826(7) 0.1735(6) 0.084(2) Uani 1 1 d . . . H23A H 0.2637 1.4713 0.1930 0.101 Uiso 1 1 calc R . . H23B H 0.2382 1.4078 0.1024 0.101 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0580(8) 0.0431(7) 0.0538(8) -0.0058(6) -0.0078(6) -0.0137(6) S2 0.0582(8) 0.0452(7) 0.0547(8) -0.0089(6) -0.0054(6) -0.0131(6) F1 0.120(3) 0.060(2) 0.061(2) -0.0067(17) -0.012(2) -0.036(2) F2 0.120(3) 0.068(2) 0.088(3) -0.016(2) -0.013(2) -0.046(2) F3 0.115(3) 0.095(3) 0.096(3) -0.038(2) -0.026(3) -0.033(2) F4 0.136(4) 0.115(3) 0.061(2) -0.030(2) -0.012(2) -0.036(3) F5 0.106(3) 0.094(3) 0.056(2) -0.0115(19) 0.002(2) -0.048(2) F6 0.083(2) 0.0552(19) 0.064(2) -0.0080(16) -0.0041(17) -0.0274(17) F7 0.091(3) 0.058(2) 0.097(3) -0.029(2) -0.012(2) -0.0230(19) F8 0.111(3) 0.101(3) 0.080(3) -0.042(2) -0.022(2) -0.025(2) F9 0.095(3) 0.114(3) 0.057(2) -0.014(2) -0.007(2) -0.037(2) F10 0.070(2) 0.077(2) 0.062(2) -0.0084(17) -0.0038(16) -0.0318(18) O1 0.065(2) 0.052(2) 0.068(3) -0.0116(19) 0.010(2) -0.0107(19) O2 0.077(3) 0.049(2) 0.075(3) -0.005(2) -0.011(2) 0.007(2) C1 0.050(3) 0.046(3) 0.053(3) -0.009(2) -0.006(2) -0.006(2) C2 0.061(3) 0.047(3) 0.050(3) -0.007(2) -0.008(3) -0.005(2) C3 0.052(3) 0.041(3) 0.057(3) -0.012(2) -0.006(2) -0.006(2) C4 0.048(3) 0.041(3) 0.056(3) -0.008(2) -0.007(2) -0.011(2) C5 0.048(3) 0.043(3) 0.053(3) -0.009(2) -0.003(2) -0.007(2) C6 0.048(3) 0.045(3) 0.055(3) -0.011(2) -0.002(2) -0.005(2) C7 0.052(3) 0.045(3) 0.065(4) -0.017(3) -0.007(3) -0.006(2) C8 0.049(3) 0.037(3) 0.059(3) -0.009(2) -0.004(2) -0.009(2) C9 0.056(3) 0.038(3) 0.057(3) -0.007(2) 0.000(2) -0.006(2) C10 0.048(3) 0.047(3) 0.056(3) -0.014(2) -0.005(2) -0.002(2) C11 0.066(3) 0.048(3) 0.051(3) -0.010(2) -0.012(3) -0.004(3) C12 0.070(4) 0.047(3) 0.073(4) -0.013(3) -0.009(3) -0.014(3) C13 0.073(4) 0.063(4) 0.074(4) -0.027(3) -0.019(3) -0.011(3) C14 0.072(4) 0.080(4) 0.059(4) -0.025(3) -0.014(3) -0.004(3) C15 0.065(4) 0.057(3) 0.053(3) -0.014(3) -0.003(3) -0.012(3) C16 0.046(3) 0.042(3) 0.060(3) -0.016(2) -0.005(2) -0.001(2) C17 0.052(3) 0.049(3) 0.066(4) -0.018(3) -0.006(3) 0.001(2) C18 0.059(3) 0.048(3) 0.074(4) -0.019(3) -0.007(3) -0.008(3) C19 0.063(4) 0.070(4) 0.077(4) -0.034(3) -0.012(3) -0.003(3) C20 0.060(3) 0.068(4) 0.056(3) -0.021(3) -0.002(3) -0.006(3) C21 0.049(3) 0.052(3) 0.064(3) -0.015(3) -0.004(3) -0.009(2) C22 0.111(6) 0.066(4) 0.075(5) -0.009(4) 0.010(4) -0.031(4) C23 0.107(6) 0.049(4) 0.089(5) 0.002(3) -0.035(4) -0.018(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C4 1.695(5) . ? S1 C1 1.750(6) . ? S2 C5 1.702(6) . ? S2 C8 1.752(5) . ? F1 C11 1.355(6) . ? F2 C12 1.353(7) . ? F3 C13 1.344(7) . ? F4 C14 1.338(7) . ? F5 C15 1.335(6) . ? F6 C17 1.347(6) . ? F7 C18 1.351(6) . ? F8 C19 1.344(7) . ? F9 C20 1.323(7) . ? F10 C21 1.337(6) . ? O1 C22 1.403(7) . ? O1 C9 1.417(6) . ? O2 C23 1.395(8) . ? O2 C9 1.428(6) . ? C1 C2 1.385(7) . ? C1 C10 1.466(8) . ? C2 C3 1.385(8) . ? C2 H2 0.9300 . ? C3 C4 1.362(7) . ? C3 C9 1.524(7) . ? C4 C5 1.465(7) . ? C5 C6 1.376(7) . ? C6 C7 1.398(7) . ? C6 C9 1.515(8) . ? C7 C8 1.377(7) . ? C7 H7 0.9300 . ? C8 C16 1.474(8) . ? C10 C15 1.397(8) . ? C10 C11 1.398(7) . ? C11 C12 1.367(8) . ? C12 C13 1.361(9) . ? C13 C14 1.356(9) . ? C14 C15 1.386(8) . ? C16 C21 1.384(8) . ? C16 C17 1.387(7) . ? C17 C18 1.371(8) . ? C18 C19 1.360(9) . ? C19 C20 1.390(8) . ? C20 C21 1.391(8) . ? C22 C23 1.481(10) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? 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 C4 S1 C1 90.8(3) . . ? C5 S2 C8 90.7(3) . . ? C22 O1 C9 106.6(5) . . ? C23 O2 C9 108.6(5) . . ? C2 C1 C10 127.8(5) . . ? C2 C1 S1 110.8(4) . . ? C10 C1 S1 121.5(4) . . ? C1 C2 C3 112.1(5) . . ? C1 C2 H2 124.0 . . ? C3 C2 H2 124.0 . . ? C4 C3 C2 113.7(5) . . ? C4 C3 C9 109.8(5) . . ? C2 C3 C9 136.5(5) . . ? C3 C4 C5 109.7(4) . . ? C3 C4 S1 112.6(4) . . ? C5 C4 S1 137.7(4) . . ? C6 C5 C4 108.5(5) . . ? C6 C5 S2 112.8(4) . . ? C4 C5 S2 138.7(4) . . ? C5 C6 C7 112.7(5) . . ? C5 C6 C9 110.1(5) . . ? C7 C6 C9 137.2(5) . . ? C8 C7 C6 112.7(5) . . ? C8 C7 H7 123.7 . . ? C6 C7 H7 123.7 . . ? C7 C8 C16 127.3(5) . . ? C7 C8 S2 111.1(4) . . ? C16 C8 S2 121.5(4) . . ? O1 C9 O2 105.8(4) . . ? O1 C9 C6 113.0(5) . . ? O2 C9 C6 112.7(4) . . ? O1 C9 C3 110.9(4) . . ? O2 C9 C3 112.7(5) . . ? C6 C9 C3 101.9(4) . . ? C15 C10 C11 113.5(5) . . ? C15 C10 C1 122.8(5) . . ? C11 C10 C1 123.7(5) . . ? F1 C11 C12 117.1(5) . . ? F1 C11 C10 119.2(5) . . ? C12 C11 C10 123.6(5) . . ? F2 C12 C13 119.9(6) . . ? F2 C12 C11 119.5(6) . . ? C13 C12 C11 120.6(5) . . ? F3 C13 C14 120.7(6) . . ? F3 C13 C12 120.5(6) . . ? C14 C13 C12 118.8(6) . . ? F4 C14 C13 120.9(6) . . ? F4 C14 C15 118.6(6) . . ? C13 C14 C15 120.5(6) . . ? F5 C15 C14 116.6(5) . . ? F5 C15 C10 120.5(5) . . ? C14 C15 C10 122.9(5) . . ? C21 C16 C17 114.9(5) . . ? C21 C16 C8 123.7(5) . . ? C17 C16 C8 121.4(5) . . ? F6 C17 C18 115.7(5) . . ? F6 C17 C16 121.0(5) . . ? C18 C17 C16 123.3(6) . . ? F7 C18 C19 119.1(6) . . ? F7 C18 C17 120.5(6) . . ? C19 C18 C17 120.3(5) . . ? F8 C19 C18 121.2(6) . . ? F8 C19 C20 119.4(6) . . ? C18 C19 C20 119.5(6) . . ? F9 C20 C19 121.2(6) . . ? F9 C20 C21 120.2(5) . . ? C19 C20 C21 118.6(6) . . ? F10 C21 C16 120.7(5) . . ? F10 C21 C20 115.9(5) . . ? C16 C21 C20 123.4(5) . . ? O1 C22 C23 104.7(6) . . ? O1 C22 H22A 110.8 . . ? C23 C22 H22A 110.8 . . ? O1 C22 H22B 110.8 . . ? C23 C22 H22B 110.8 . . ? H22A C22 H22B 108.9 . . ? O2 C23 C22 106.0(5) . . ? O2 C23 H23A 110.5 . . ? C22 C23 H23A 110.5 . . ? O2 C23 H23B 110.5 . . ? C22 C23 H23B 110.5 . . ? H23A C23 H23B 108.7 . . ? 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 -0.6(4) . . . . ? C4 S1 C1 C10 179.7(5) . . . . ? C10 C1 C2 C3 179.7(5) . . . . ? S1 C1 C2 C3 0.0(6) . . . . ? C1 C2 C3 C4 0.8(7) . . . . ? C1 C2 C3 C9 179.5(6) . . . . ? C2 C3 C4 C5 179.0(5) . . . . ? C9 C3 C4 C5 0.0(6) . . . . ? C2 C3 C4 S1 -1.3(6) . . . . ? C9 C3 C4 S1 179.7(4) . . . . ? C1 S1 C4 C3 1.1(4) . . . . ? C1 S1 C4 C5 -179.3(6) . . . . ? C3 C4 C5 C6 0.1(6) . . . . ? S1 C4 C5 C6 -179.5(5) . . . . ? C3 C4 C5 S2 -179.2(5) . . . . ? S1 C4 C5 S2 1.2(10) . . . . ? C8 S2 C5 C6 -0.2(4) . . . . ? C8 S2 C5 C4 179.0(6) . . . . ? C4 C5 C6 C7 179.9(4) . . . . ? S2 C5 C6 C7 -0.6(6) . . . . ? C4 C5 C6 C9 -0.1(6) . . . . ? S2 C5 C6 C9 179.4(4) . . . . ? C5 C6 C7 C8 1.5(7) . . . . ? C9 C6 C7 C8 -178.6(6) . . . . ? C6 C7 C8 C16 -179.2(5) . . . . ? C6 C7 C8 S2 -1.6(6) . . . . ? C5 S2 C8 C7 1.1(4) . . . . ? C5 S2 C8 C16 178.8(4) . . . . ? C22 O1 C9 O2 27.2(6) . . . . ? C22 O1 C9 C6 -96.6(6) . . . . ? C22 O1 C9 C3 149.7(5) . . . . ? C23 O2 C9 O1 -14.3(6) . . . . ? C23 O2 C9 C6 109.7(6) . . . . ? C23 O2 C9 C3 -135.6(5) . . . . ? C5 C6 C9 O1 -119.0(5) . . . . ? C7 C6 C9 O1 61.1(8) . . . . ? C5 C6 C9 O2 121.1(5) . . . . ? C7 C6 C9 O2 -58.8(8) . . . . ? C5 C6 C9 C3 0.0(6) . . . . ? C7 C6 C9 C3 -179.9(6) . . . . ? C4 C3 C9 O1 120.5(5) . . . . ? C2 C3 C9 O1 -58.2(8) . . . . ? C4 C3 C9 O2 -121.1(5) . . . . ? C2 C3 C9 O2 60.2(8) . . . . ? C4 C3 C9 C6 0.0(6) . . . . ? C2 C3 C9 C6 -178.7(6) . . . . ? C2 C1 C10 C15 11.6(9) . . . . ? S1 C1 C10 C15 -168.9(4) . . . . ? C2 C1 C10 C11 -168.3(6) . . . . ? S1 C1 C10 C11 11.3(8) . . . . ? C15 C10 C11 F1 -179.0(5) . . . . ? C1 C10 C11 F1 0.8(8) . . . . ? C15 C10 C11 C12 -2.2(8) . . . . ? C1 C10 C11 C12 177.6(5) . . . . ? F1 C11 C12 F2 -1.1(9) . . . . ? C10 C11 C12 F2 -177.9(5) . . . . ? F1 C11 C12 C13 177.6(6) . . . . ? C10 C11 C12 C13 0.7(10) . . . . ? F2 C12 C13 F3 1.4(10) . . . . ? C11 C12 C13 F3 -177.2(6) . . . . ? F2 C12 C13 C14 178.6(6) . . . . ? C11 C12 C13 C14 0.0(10) . . . . ? F3 C13 C14 F4 -2.6(10) . . . . ? C12 C13 C14 F4 -179.8(6) . . . . ? F3 C13 C14 C15 178.3(6) . . . . ? C12 C13 C14 C15 1.1(10) . . . . ? F4 C14 C15 F5 -0.9(9) . . . . ? C13 C14 C15 F5 178.2(6) . . . . ? F4 C14 C15 C10 178.0(6) . . . . ? C13 C14 C15 C10 -2.9(10) . . . . ? C11 C10 C15 F5 -177.9(5) . . . . ? C1 C10 C15 F5 2.3(9) . . . . ? C11 C10 C15 C14 3.3(8) . . . . ? C1 C10 C15 C14 -176.6(6) . . . . ? C7 C8 C16 C21 165.1(5) . . . . ? S2 C8 C16 C21 -12.2(7) . . . . ? C7 C8 C16 C17 -14.4(8) . . . . ? S2 C8 C16 C17 168.3(4) . . . . ? C21 C16 C17 F6 178.1(5) . . . . ? C8 C16 C17 F6 -2.4(8) . . . . ? C21 C16 C17 C18 -1.0(8) . . . . ? C8 C16 C17 C18 178.5(5) . . . . ? F6 C17 C18 F7 2.6(8) . . . . ? C16 C17 C18 F7 -178.2(5) . . . . ? F6 C17 C18 C19 -179.0(5) . . . . ? C16 C17 C18 C19 0.1(9) . . . . ? F7 C18 C19 F8 -1.7(9) . . . . ? C17 C18 C19 F8 179.9(5) . . . . ? F7 C18 C19 C20 179.4(5) . . . . ? C17 C18 C19 C20 1.0(9) . . . . ? F8 C19 C20 F9 2.2(9) . . . . ? C18 C19 C20 F9 -178.9(6) . . . . ? F8 C19 C20 C21 179.9(5) . . . . ? C18 C19 C20 C21 -1.2(9) . . . . ? C17 C16 C21 F10 179.3(5) . . . . ? C8 C16 C21 F10 -0.3(8) . . . . ? C17 C16 C21 C20 0.8(8) . . . . ? C8 C16 C21 C20 -178.7(5) . . . . ? F9 C20 C21 F10 -0.6(8) . . . . ? C19 C20 C21 F10 -178.3(5) . . . . ? F9 C20 C21 C16 178.0(5) . . . . ? C19 C20 C21 C16 0.3(9) . . . . ? C9 O1 C22 C23 -28.9(7) . . . . ? C9 O2 C23 C22 -3.3(8) . . . . ? O1 C22 C23 O2 19.8(8) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.352 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.074 #===END #Compound 6 data_js13b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H2 F10 N2 S2' _chemical_formula_weight 572.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.8693(5) _cell_length_b 7.6992(2) _cell_length_c 32.7451(9) _cell_angle_alpha 90.00 _cell_angle_beta 96.7830(12) _cell_angle_gamma 90.00 _cell_volume 4223.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour 'Dark-Blue' _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.00 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.801 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2256 _exptl_absorpt_coefficient_mu 0.359 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13859 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0696 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 25.03 _reflns_number_total 7395 _reflns_number_gt 4474 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0327P)^2^+2.0948P] 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 7395 _refine_ls_number_parameters 685 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1085 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 S1 S 0.37398(5) 0.31916(13) 0.31548(3) 0.0555(3) Uani 1 1 d . . . S2 S 0.44459(5) 0.25919(11) 0.20294(3) 0.0486(2) Uani 1 1 d . . . N1 N 0.6827(2) 0.6451(4) 0.38158(10) 0.0759(10) Uani 1 1 d . . . N2 N 0.7742(2) 0.5499(6) 0.26490(10) 0.0957(13) Uani 1 1 d . . . F1 F 0.25654(13) 0.4296(4) 0.36838(7) 0.0982(8) Uani 1 1 d . . . F2 F 0.19605(15) 0.3952(4) 0.43980(8) 0.1171(10) Uani 1 1 d . . . F3 F 0.29357(17) 0.3443(4) 0.51066(8) 0.1164(10) Uani 1 1 d . . . F4 F 0.45377(18) 0.3284(4) 0.50866(8) 0.1217(10) Uani 1 1 d . . . F5 F 0.51481(15) 0.3508(4) 0.43796(7) 0.1016(9) Uani 1 1 d . . . F6 F 0.66879(12) 0.4232(3) 0.14438(6) 0.0816(7) Uani 1 1 d . . . F7 F 0.68701(13) 0.3612(3) 0.06687(6) 0.0822(7) Uani 1 1 d . . . F8 F 0.57900(13) 0.1695(3) 0.01867(6) 0.0768(6) Uani 1 1 d . . . F9 F 0.44741(15) 0.0490(3) 0.05015(6) 0.0986(8) Uani 1 1 d . . . F10 F 0.42562(13) 0.1136(3) 0.12743(6) 0.0817(7) Uani 1 1 d . . . C1 C 0.4232(2) 0.4026(5) 0.36134(10) 0.0529(9) Uani 1 1 d . . . C2 C 0.4973(2) 0.4642(4) 0.35600(10) 0.0514(9) Uani 1 1 d . . . H2 H 0.5319 0.5149 0.3768 0.062 Uiso 1 1 calc R . . C3 C 0.5153(2) 0.4424(4) 0.31552(10) 0.0461(8) Uani 1 1 d . . . C4 C 0.45401(19) 0.3647(4) 0.29022(10) 0.0454(8) Uani 1 1 d . . . C5 C 0.47987(19) 0.3402(4) 0.24962(9) 0.0437(8) Uani 1 1 d . . . C6 C 0.55731(19) 0.4004(4) 0.25064(9) 0.0417(8) Uani 1 1 d . . . C7 C 0.5884(2) 0.3804(4) 0.21334(9) 0.0444(8) Uani 1 1 d . . . H7 H 0.6398 0.4138 0.2090 0.053 Uiso 1 1 calc R . . C8 C 0.53449(18) 0.3056(4) 0.18358(9) 0.0430(8) Uani 1 1 d . . . C9 C 0.58318(19) 0.4682(4) 0.29224(9) 0.0428(8) Uani 1 1 d . . . C10 C 0.6546(2) 0.5373(4) 0.30680(9) 0.0458(8) Uani 1 1 d . . . C11 C 0.6706(2) 0.5994(5) 0.34842(12) 0.0545(9) Uani 1 1 d . . . C12 C 0.7204(2) 0.5460(5) 0.28286(11) 0.0615(10) Uani 1 1 d . . . C13 C 0.3879(2) 0.3916(5) 0.40002(11) 0.0561(10) Uani 1 1 d . . . C14 C 0.3067(2) 0.4013(5) 0.40274(12) 0.0661(11) Uani 1 1 d . . . C15 C 0.2753(3) 0.3859(6) 0.43920(16) 0.0791(13) Uani 1 1 d . . . C16 C 0.3239(3) 0.3605(6) 0.47500(14) 0.0794(13) Uani 1 1 d . . . C17 C 0.4043(3) 0.3520(6) 0.47398(13) 0.0807(13) Uani 1 1 d . . . C18 C 0.4349(3) 0.3663(5) 0.43721(13) 0.0712(11) Uani 1 1 d . . . C19 C 0.5464(2) 0.2688(4) 0.14072(10) 0.0456(8) Uani 1 1 d . . . C20 C 0.6126(2) 0.3263(5) 0.12250(10) 0.0501(9) Uani 1 1 d . . . C21 C 0.6235(2) 0.2960(5) 0.08232(11) 0.0542(9) Uani 1 1 d . . . C22 C 0.5685(2) 0.2019(5) 0.05761(11) 0.0560(10) Uani 1 1 d . . . C23 C 0.5025(2) 0.1415(5) 0.07357(11) 0.0612(10) Uani 1 1 d . . . C24 C 0.4922(2) 0.1756(5) 0.11381(11) 0.0540(9) Uani 1 1 d . . . S1A S 0.85522(5) 0.52780(11) 0.18440(3) 0.0493(2) Uani 1 1 d . . . S2A S 0.94387(5) 0.34222(11) 0.29483(3) 0.0479(2) Uani 1 1 d . . . N1A N 1.1510(2) 0.3639(7) 0.11229(12) 0.1293(18) Uani 1 1 d . . . N2A N 1.2656(2) 0.1990(5) 0.23331(11) 0.0884(12) Uani 1 1 d . . . F1A F 0.75761(12) 0.7598(3) 0.13724(6) 0.0655(6) Uani 1 1 d . . . F2A F 0.67926(14) 0.8922(3) 0.06880(7) 0.0860(7) Uani 1 1 d . . . F3A F 0.72020(15) 0.8009(3) -0.00614(7) 0.0963(8) Uani 1 1 d . . . F4A F 0.84440(17) 0.5817(4) -0.01068(7) 0.1137(10) Uani 1 1 d . . . F5A F 0.92669(15) 0.4589(3) 0.05682(6) 0.0953(8) Uani 1 1 d . . . F6A F 1.17981(13) 0.0744(3) 0.34589(6) 0.0846(7) Uani 1 1 d . . . F7A F 1.20334(17) -0.0485(4) 0.42160(7) 0.1268(11) Uani 1 1 d . . . F8A F 1.09436(15) -0.0088(3) 0.47476(6) 0.0936(8) Uani 1 1 d . . . F9A F 0.95709(14) 0.1620(3) 0.44979(6) 0.0851(7) Uani 1 1 d . . . F10A F 0.92949(13) 0.2869(3) 0.37415(6) 0.0825(7) Uani 1 1 d . . . C1A C 0.8945(2) 0.5411(4) 0.13764(10) 0.0471(8) Uani 1 1 d . . . C2A C 0.9718(2) 0.4816(4) 0.14110(10) 0.0514(9) Uani 1 1 d . . . H2A H 1.0031 0.4806 0.1195 0.062 Uiso 1 1 calc R . . C3A C 0.9983(2) 0.4221(4) 0.18113(10) 0.0457(8) Uani 1 1 d . . . C4A C 0.94097(18) 0.4390(4) 0.20772(9) 0.0431(8) Uani 1 1 d . . . C5A C 0.97375(19) 0.3748(4) 0.24807(9) 0.0437(8) Uani 1 1 d . . . C6A C 1.05148(19) 0.3224(4) 0.24612(9) 0.0436(8) Uani 1 1 d . . . C7A C 1.08788(19) 0.2557(4) 0.28371(9) 0.0475(8) Uani 1 1 d . . . H7A H 1.1403 0.2164 0.2879 0.057 Uiso 1 1 calc R . . C8A C 1.03715(18) 0.2552(4) 0.31356(9) 0.0434(8) Uani 1 1 d . . . C9A C 1.07111(19) 0.3493(4) 0.20410(10) 0.0465(8) Uani 1 1 d . . . C10A C 1.1408(2) 0.3157(5) 0.18902(10) 0.0548(9) Uani 1 1 d . . . C11A C 1.1485(2) 0.3431(6) 0.14633(14) 0.0761(12) Uani 1 1 d . . . C12A C 1.2103(2) 0.2498(5) 0.21386(12) 0.0628(10) Uani 1 1 d . . . C13A C 0.8469(2) 0.6066(4) 0.10038(10) 0.0490(9) Uani 1 1 d . . . C14A C 0.7819(2) 0.7145(5) 0.10098(11) 0.0541(9) Uani 1 1 d . . . C15A C 0.7399(2) 0.7828(5) 0.06580(12) 0.0617(10) Uani 1 1 d . . . C16A C 0.7605(3) 0.7373(5) 0.02828(12) 0.0680(11) Uani 1 1 d . . . C17A C 0.8234(3) 0.6275(6) 0.02595(11) 0.0718(12) Uani 1 1 d . . . C18A C 0.8652(2) 0.5655(5) 0.06135(12) 0.0649(10) Uani 1 1 d . . . C19A C 1.0533(2) 0.1894(4) 0.35600(10) 0.0467(8) Uani 1 1 d . . . C20A C 1.1223(2) 0.0999(5) 0.37049(11) 0.0578(10) Uani 1 1 d . . . C21A C 1.1361(2) 0.0350(6) 0.40967(12) 0.0707(11) Uani 1 1 d . . . C22A C 1.0816(3) 0.0557(5) 0.43682(11) 0.0640(11) Uani 1 1 d . . . C23A C 1.0126(2) 0.1418(5) 0.42425(11) 0.0577(10) Uani 1 1 d . . . C24A C 0.9998(2) 0.2047(5) 0.38476(11) 0.0545(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 S1 0.0495(6) 0.0647(6) 0.0536(6) -0.0018(5) 0.0113(4) 0.0009(5) S2 0.0472(5) 0.0521(6) 0.0460(5) -0.0021(4) 0.0027(4) -0.0005(4) N1 0.091(3) 0.079(3) 0.055(2) -0.0068(19) -0.0035(19) 0.002(2) N2 0.070(3) 0.157(4) 0.063(2) -0.016(2) 0.018(2) -0.032(3) F1 0.0593(15) 0.159(2) 0.0777(17) -0.0282(16) 0.0151(13) -0.0072(15) F2 0.0777(18) 0.168(3) 0.115(2) -0.0474(19) 0.0498(16) -0.0296(18) F3 0.143(2) 0.137(2) 0.0835(18) 0.0075(16) 0.0727(18) -0.0066(19) F4 0.138(2) 0.168(3) 0.0621(17) 0.0405(18) 0.0239(16) 0.028(2) F5 0.0764(17) 0.167(3) 0.0630(15) 0.0312(15) 0.0163(13) 0.0389(17) F6 0.0659(14) 0.128(2) 0.0524(13) -0.0256(13) 0.0110(11) -0.0322(14) F7 0.0684(15) 0.127(2) 0.0541(13) -0.0102(13) 0.0198(11) -0.0116(14) F8 0.1003(18) 0.0905(16) 0.0398(13) -0.0098(11) 0.0096(11) 0.0045(13) F9 0.121(2) 0.116(2) 0.0568(14) -0.0297(14) 0.0022(14) -0.0462(17) F10 0.0835(17) 0.1034(18) 0.0581(14) -0.0155(12) 0.0081(12) -0.0420(14) C1 0.052(2) 0.060(2) 0.048(2) 0.0031(18) 0.0121(18) 0.0086(18) C2 0.057(2) 0.055(2) 0.042(2) -0.0044(17) 0.0052(18) 0.0052(18) C3 0.048(2) 0.047(2) 0.044(2) 0.0022(17) 0.0045(17) 0.0051(17) C4 0.046(2) 0.046(2) 0.045(2) 0.0022(17) 0.0077(16) 0.0066(17) C5 0.047(2) 0.043(2) 0.041(2) 0.0012(16) 0.0044(16) 0.0070(16) C6 0.044(2) 0.043(2) 0.038(2) 0.0026(15) 0.0024(15) 0.0033(16) C7 0.048(2) 0.042(2) 0.042(2) 0.0040(16) 0.0040(17) 0.0031(16) C8 0.043(2) 0.042(2) 0.043(2) -0.0020(16) 0.0015(16) 0.0027(16) C9 0.048(2) 0.043(2) 0.0376(19) 0.0026(16) 0.0043(16) 0.0042(16) C10 0.052(2) 0.050(2) 0.036(2) 0.0031(17) 0.0051(17) 0.0008(18) C11 0.060(2) 0.053(2) 0.049(2) 0.003(2) 0.0016(19) -0.0013(18) C12 0.059(3) 0.079(3) 0.045(2) -0.006(2) -0.002(2) -0.013(2) C13 0.057(2) 0.059(2) 0.055(2) -0.0005(19) 0.020(2) 0.0037(19) C14 0.063(3) 0.080(3) 0.056(3) -0.014(2) 0.013(2) -0.007(2) C15 0.070(3) 0.088(3) 0.087(4) -0.024(3) 0.038(3) -0.015(2) C16 0.101(4) 0.080(3) 0.066(3) -0.002(2) 0.048(3) -0.005(3) C17 0.100(4) 0.095(3) 0.050(3) 0.015(2) 0.021(3) 0.012(3) C18 0.071(3) 0.084(3) 0.063(3) 0.014(2) 0.024(2) 0.017(2) C19 0.052(2) 0.042(2) 0.042(2) -0.0021(16) 0.0016(17) 0.0049(17) C20 0.048(2) 0.059(2) 0.042(2) -0.0092(18) -0.0024(17) 0.0049(18) C21 0.048(2) 0.069(3) 0.046(2) -0.002(2) 0.0064(18) 0.0055(19) C22 0.068(3) 0.063(3) 0.038(2) -0.0051(19) 0.0063(19) 0.008(2) C23 0.082(3) 0.054(3) 0.044(2) -0.0125(19) -0.009(2) -0.008(2) C24 0.058(2) 0.051(2) 0.053(2) -0.0007(19) 0.0063(19) -0.0083(19) S1A 0.0501(6) 0.0542(6) 0.0430(5) 0.0000(4) 0.0024(4) 0.0001(4) S2A 0.0495(5) 0.0536(6) 0.0404(5) 0.0003(4) 0.0050(4) -0.0021(4) N1A 0.082(3) 0.247(6) 0.063(3) 0.021(3) 0.027(2) 0.002(3) N2A 0.056(2) 0.133(3) 0.074(2) -0.012(2) 0.0003(19) 0.014(2) F1A 0.0660(14) 0.0725(14) 0.0573(14) 0.0052(11) 0.0039(10) 0.0071(11) F2A 0.0748(16) 0.0879(17) 0.0909(17) 0.0179(13) -0.0090(13) 0.0159(14) F3A 0.112(2) 0.1045(18) 0.0626(15) 0.0209(13) -0.0303(14) -0.0055(15) F4A 0.139(2) 0.156(3) 0.0435(14) -0.0052(15) -0.0014(14) 0.0260(19) F5A 0.110(2) 0.125(2) 0.0484(13) -0.0142(13) -0.0004(13) 0.0399(17) F6A 0.0671(15) 0.127(2) 0.0607(14) 0.0239(13) 0.0106(12) 0.0257(14) F7A 0.102(2) 0.203(3) 0.0762(17) 0.0533(19) 0.0110(15) 0.065(2) F8A 0.119(2) 0.1125(19) 0.0487(14) 0.0239(13) 0.0051(13) 0.0176(15) F9A 0.0925(18) 0.1141(19) 0.0520(14) 0.0122(13) 0.0220(12) 0.0074(15) F10A 0.0746(16) 0.122(2) 0.0529(13) 0.0154(13) 0.0169(11) 0.0255(14) C1A 0.051(2) 0.044(2) 0.045(2) 0.0001(17) -0.0001(17) -0.0044(17) C2A 0.061(2) 0.054(2) 0.040(2) 0.0019(17) 0.0071(17) -0.0084(18) C3A 0.048(2) 0.048(2) 0.041(2) 0.0030(16) 0.0043(17) -0.0058(17) C4A 0.043(2) 0.044(2) 0.042(2) -0.0045(16) -0.0001(16) -0.0067(16) C5A 0.044(2) 0.044(2) 0.043(2) -0.0030(16) 0.0021(16) -0.0027(16) C6A 0.045(2) 0.046(2) 0.039(2) -0.0042(16) 0.0033(15) -0.0061(16) C7A 0.0424(19) 0.056(2) 0.043(2) -0.0029(17) -0.0008(16) -0.0017(17) C8A 0.0422(19) 0.046(2) 0.041(2) 0.0008(16) -0.0008(15) -0.0017(16) C9A 0.047(2) 0.050(2) 0.043(2) -0.0022(17) 0.0064(17) -0.0089(17) C10A 0.047(2) 0.071(3) 0.046(2) -0.0015(19) 0.0035(18) -0.0071(19) C11A 0.051(2) 0.120(4) 0.059(3) 0.002(3) 0.012(2) -0.006(2) C12A 0.047(2) 0.087(3) 0.056(2) -0.013(2) 0.014(2) -0.003(2) C13A 0.054(2) 0.052(2) 0.039(2) 0.0002(17) -0.0011(17) -0.0076(18) C14A 0.063(3) 0.052(2) 0.046(2) 0.0036(19) -0.0012(19) -0.0094(19) C15A 0.062(3) 0.057(3) 0.063(3) 0.006(2) -0.005(2) -0.004(2) C16A 0.084(3) 0.066(3) 0.049(3) 0.014(2) -0.018(2) -0.007(2) C17A 0.088(3) 0.088(3) 0.037(2) -0.004(2) -0.007(2) -0.005(3) C18A 0.071(3) 0.064(3) 0.058(3) -0.005(2) -0.002(2) 0.009(2) C19A 0.050(2) 0.049(2) 0.039(2) -0.0022(17) 0.0011(16) -0.0100(17) C20A 0.056(2) 0.067(3) 0.050(2) 0.003(2) 0.0080(19) 0.001(2) C21A 0.068(3) 0.094(3) 0.048(3) 0.018(2) -0.001(2) 0.018(2) C22A 0.088(3) 0.066(3) 0.036(2) 0.011(2) -0.003(2) -0.003(2) C23A 0.076(3) 0.060(3) 0.039(2) -0.0011(19) 0.014(2) -0.009(2) C24A 0.058(2) 0.057(2) 0.048(2) 0.0011(19) 0.0045(19) -0.0008(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C4 1.701(3) . ? S1 C1 1.750(4) . ? S2 C5 1.693(3) . ? S2 C8 1.748(3) . ? N1 C11 1.137(4) . ? N2 C12 1.138(4) . ? F1 C14 1.343(4) . ? F2 C15 1.342(4) . ? F3 C16 1.335(4) . ? F4 C17 1.340(5) . ? F5 C18 1.351(4) . ? F6 C20 1.345(4) . ? F7 C21 1.335(4) . ? F8 C22 1.331(4) . ? F9 C23 1.338(4) . ? F10 C24 1.343(4) . ? C1 C2 1.368(4) . ? C1 C13 1.464(4) . ? C2 C3 1.404(4) . ? C2 H2 0.9300 . ? C3 C4 1.382(4) . ? C3 C9 1.462(4) . ? C4 C5 1.459(4) . ? C5 C6 1.383(4) . ? C6 C7 1.394(4) . ? C6 C9 1.476(4) . ? C7 C8 1.378(4) . ? C7 H7 0.9300 . ? C8 C19 1.469(4) . ? C9 C10 1.352(4) . ? C10 C12 1.434(5) . ? C10 C11 1.440(5) . ? C13 C14 1.385(5) . ? C13 C18 1.386(5) . ? C14 C15 1.367(5) . ? C15 C16 1.363(6) . ? C16 C17 1.362(6) . ? C17 C18 1.369(5) . ? C19 C24 1.392(4) . ? C19 C20 1.399(4) . ? C20 C21 1.370(4) . ? C21 C22 1.365(5) . ? C22 C23 1.367(5) . ? C23 C24 1.375(5) . ? S1A C4A 1.698(3) . ? S1A C1A 1.742(3) . ? S2A C5A 1.687(3) . ? S2A C8A 1.753(3) . ? N1A C11A 1.132(5) . ? N2A C12A 1.136(4) . ? F1A C14A 1.347(4) . ? F2A C15A 1.338(4) . ? F3A C16A 1.339(4) . ? F4A C17A 1.337(4) . ? F5A C18A 1.345(4) . ? F6A C20A 1.346(4) . ? F7A C21A 1.322(4) . ? F8A C22A 1.332(4) . ? F9A C23A 1.336(4) . ? F10A C24A 1.352(4) . ? C1A C2A 1.374(4) . ? C1A C13A 1.468(4) . ? C2A C3A 1.410(4) . ? C2A H2A 0.9300 . ? C3A C4A 1.381(4) . ? C3A C9A 1.474(4) . ? C4A C5A 1.457(4) . ? C5A C6A 1.381(4) . ? C6A C7A 1.406(4) . ? C6A C9A 1.467(4) . ? C7A C8A 1.373(4) . ? C7A H7A 0.9300 . ? C8A C19A 1.474(4) . ? C9A C10A 1.353(4) . ? C10A C11A 1.435(5) . ? C10A C12A 1.438(5) . ? C13A C14A 1.378(5) . ? C13A C18A 1.386(5) . ? C14A C15A 1.383(5) . ? C15A C16A 1.361(5) . ? C16A C17A 1.365(5) . ? C17A C18A 1.370(5) . ? C19A C24A 1.384(4) . ? C19A C20A 1.388(5) . ? C20A C21A 1.371(5) . ? C21A C22A 1.362(5) . ? C22A C23A 1.360(5) . ? C23A C24A 1.374(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 S1 C1 91.07(17) . . ? C5 S2 C8 91.40(16) . . ? C2 C1 C13 127.0(3) . . ? C2 C1 S1 111.4(3) . . ? C13 C1 S1 121.4(3) . . ? C1 C2 C3 112.4(3) . . ? C1 C2 H2 123.8 . . ? C3 C2 H2 123.8 . . ? C4 C3 C2 112.8(3) . . ? C4 C3 C9 108.8(3) . . ? C2 C3 C9 138.2(3) . . ? C3 C4 C5 108.6(3) . . ? C3 C4 S1 112.2(2) . . ? C5 C4 S1 139.1(3) . . ? C6 C5 C4 108.5(3) . . ? C6 C5 S2 112.1(2) . . ? C4 C5 S2 139.4(3) . . ? C5 C6 C7 113.2(3) . . ? C5 C6 C9 108.4(3) . . ? C7 C6 C9 138.3(3) . . ? C8 C7 C6 112.3(3) . . ? C8 C7 H7 123.8 . . ? C6 C7 H7 123.8 . . ? C7 C8 C19 127.1(3) . . ? C7 C8 S2 111.0(2) . . ? C19 C8 S2 122.0(2) . . ? C10 C9 C3 126.2(3) . . ? C10 C9 C6 128.2(3) . . ? C3 C9 C6 105.6(3) . . ? C9 C10 C12 122.8(3) . . ? C9 C10 C11 121.6(3) . . ? C12 C10 C11 115.5(3) . . ? N1 C11 C10 178.5(4) . . ? N2 C12 C10 177.7(4) . . ? C14 C13 C18 114.7(3) . . ? C14 C13 C1 124.0(4) . . ? C18 C13 C1 121.3(3) . . ? F1 C14 C15 118.4(4) . . ? F1 C14 C13 119.0(3) . . ? C15 C14 C13 122.6(4) . . ? F2 C15 C16 119.6(4) . . ? F2 C15 C14 119.8(5) . . ? C16 C15 C14 120.6(4) . . ? F3 C16 C17 120.2(5) . . ? F3 C16 C15 120.8(4) . . ? C17 C16 C15 119.0(4) . . ? F4 C17 C16 120.5(4) . . ? F4 C17 C18 119.6(4) . . ? C16 C17 C18 119.8(4) . . ? F5 C18 C17 117.1(4) . . ? F5 C18 C13 119.6(3) . . ? C17 C18 C13 123.2(4) . . ? C24 C19 C20 113.0(3) . . ? C24 C19 C8 123.4(3) . . ? C20 C19 C8 123.5(3) . . ? F6 C20 C21 116.1(3) . . ? F6 C20 C19 119.8(3) . . ? C21 C20 C19 124.1(3) . . ? F7 C21 C22 119.6(3) . . ? F7 C21 C20 120.3(3) . . ? C22 C21 C20 120.0(3) . . ? F8 C22 C21 120.7(3) . . ? F8 C22 C23 120.6(3) . . ? C21 C22 C23 118.8(3) . . ? F9 C23 C22 120.3(3) . . ? F9 C23 C24 119.5(4) . . ? C22 C23 C24 120.2(3) . . ? F10 C24 C23 117.1(3) . . ? F10 C24 C19 119.0(3) . . ? C23 C24 C19 123.8(3) . . ? C4A S1A C1A 91.51(16) . . ? C5A S2A C8A 91.28(16) . . ? C2A C1A C13A 127.1(3) . . ? C2A C1A S1A 111.3(2) . . ? C13A C1A S1A 121.5(3) . . ? C1A C2A C3A 112.2(3) . . ? C1A C2A H2A 123.9 . . ? C3A C2A H2A 123.9 . . ? C4A C3A C2A 112.8(3) . . ? C4A C3A C9A 108.5(3) . . ? C2A C3A C9A 138.7(3) . . ? C3A C4A C5A 108.7(3) . . ? C3A C4A S1A 112.1(2) . . ? C5A C4A S1A 139.2(3) . . ? C6A C5A C4A 108.5(3) . . ? C6A C5A S2A 112.7(2) . . ? C4A C5A S2A 138.7(3) . . ? C5A C6A C7A 112.6(3) . . ? C5A C6A C9A 108.8(3) . . ? C7A C6A C9A 138.5(3) . . ? C8A C7A C6A 112.3(3) . . ? C8A C7A H7A 123.8 . . ? C6A C7A H7A 123.8 . . ? C7A C8A C19A 127.7(3) . . ? C7A C8A S2A 111.0(2) . . ? C19A C8A S2A 121.3(2) . . ? C10A C9A C6A 128.1(3) . . ? C10A C9A C3A 126.5(3) . . ? C6A C9A C3A 105.4(3) . . ? C9A C10A C11A 120.7(3) . . ? C9A C10A C12A 123.1(3) . . ? C11A C10A C12A 116.2(3) . . ? N1A C11A C10A 177.0(4) . . ? N2A C12A C10A 179.3(5) . . ? C14A C13A C18A 114.5(3) . . ? C14A C13A C1A 123.6(3) . . ? C18A C13A C1A 121.9(3) . . ? F1A C14A C13A 119.6(3) . . ? F1A C14A C15A 117.2(3) . . ? C13A C14A C15A 123.2(4) . . ? F2A C15A C16A 120.5(4) . . ? F2A C15A C14A 119.9(4) . . ? C16A C15A C14A 119.6(4) . . ? F3A C16A C15A 120.5(4) . . ? F3A C16A C17A 120.0(4) . . ? C15A C16A C17A 119.5(4) . . ? F4A C17A C16A 120.2(4) . . ? F4A C17A C18A 120.2(4) . . ? C16A C17A C18A 119.6(4) . . ? F5A C18A C17A 116.5(4) . . ? F5A C18A C13A 120.0(3) . . ? C17A C18A C13A 123.5(4) . . ? C24A C19A C20A 113.4(3) . . ? C24A C19A C8A 123.4(3) . . ? C20A C19A C8A 123.1(3) . . ? F6A C20A C21A 116.9(3) . . ? F6A C20A C19A 120.2(3) . . ? C21A C20A C19A 122.9(4) . . ? F7A C21A C22A 119.1(3) . . ? F7A C21A C20A 119.9(4) . . ? C22A C21A C20A 121.0(4) . . ? F8A C22A C23A 120.2(4) . . ? F8A C22A C21A 121.2(4) . . ? C23A C22A C21A 118.6(3) . . ? F9A C23A C22A 120.3(3) . . ? F9A C23A C24A 120.3(4) . . ? C22A C23A C24A 119.4(4) . . ? F10A C24A C23A 116.3(3) . . ? F10A C24A C19A 119.2(3) . . ? C23A C24A C19A 124.6(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 1.0(3) . . . . ? C4 S1 C1 C13 -174.9(3) . . . . ? C13 C1 C2 C3 174.7(3) . . . . ? S1 C1 C2 C3 -0.9(4) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? C1 C2 C3 C9 -174.6(4) . . . . ? C2 C3 C4 C5 -177.3(3) . . . . ? C9 C3 C4 C5 -0.9(4) . . . . ? C2 C3 C4 S1 0.4(4) . . . . ? C9 C3 C4 S1 176.8(2) . . . . ? C1 S1 C4 C3 -0.8(3) . . . . ? C1 S1 C4 C5 175.9(4) . . . . ? C3 C4 C5 C6 1.1(4) . . . . ? S1 C4 C5 C6 -175.7(3) . . . . ? C3 C4 C5 S2 179.9(3) . . . . ? S1 C4 C5 S2 3.1(6) . . . . ? C8 S2 C5 C6 -0.1(3) . . . . ? C8 S2 C5 C4 -178.8(4) . . . . ? C4 C5 C6 C7 179.0(3) . . . . ? S2 C5 C6 C7 -0.1(4) . . . . ? C4 C5 C6 C9 -0.8(4) . . . . ? S2 C5 C6 C9 -180.0(2) . . . . ? C5 C6 C7 C8 0.3(4) . . . . ? C9 C6 C7 C8 -179.9(3) . . . . ? C6 C7 C8 C19 178.7(3) . . . . ? C6 C7 C8 S2 -0.4(3) . . . . ? C5 S2 C8 C7 0.3(2) . . . . ? C5 S2 C8 C19 -178.8(3) . . . . ? C4 C3 C9 C10 -178.5(3) . . . . ? C2 C3 C9 C10 -3.5(6) . . . . ? C4 C3 C9 C6 0.4(3) . . . . ? C2 C3 C9 C6 175.4(4) . . . . ? C5 C6 C9 C10 179.2(3) . . . . ? C7 C6 C9 C10 -0.6(6) . . . . ? C5 C6 C9 C3 0.3(3) . . . . ? C7 C6 C9 C3 -179.5(4) . . . . ? C3 C9 C10 C12 175.0(3) . . . . ? C6 C9 C10 C12 -3.6(5) . . . . ? C3 C9 C10 C11 -1.8(5) . . . . ? C6 C9 C10 C11 179.6(3) . . . . ? C2 C1 C13 C14 151.0(4) . . . . ? S1 C1 C13 C14 -33.8(5) . . . . ? C2 C1 C13 C18 -30.5(6) . . . . ? S1 C1 C13 C18 144.8(3) . . . . ? C18 C13 C14 F1 178.5(3) . . . . ? C1 C13 C14 F1 -2.9(6) . . . . ? C18 C13 C14 C15 -0.5(6) . . . . ? C1 C13 C14 C15 178.2(4) . . . . ? F1 C14 C15 F2 1.5(6) . . . . ? C13 C14 C15 F2 -179.5(4) . . . . ? F1 C14 C15 C16 -178.7(4) . . . . ? C13 C14 C15 C16 0.2(7) . . . . ? F2 C15 C16 F3 0.2(7) . . . . ? C14 C15 C16 F3 -179.6(4) . . . . ? F2 C15 C16 C17 -179.7(4) . . . . ? C14 C15 C16 C17 0.5(7) . . . . ? F3 C16 C17 F4 -0.4(7) . . . . ? C15 C16 C17 F4 179.5(4) . . . . ? F3 C16 C17 C18 179.1(4) . . . . ? C15 C16 C17 C18 -1.0(7) . . . . ? F4 C17 C18 F5 1.7(6) . . . . ? C16 C17 C18 F5 -177.7(4) . . . . ? F4 C17 C18 C13 -179.7(4) . . . . ? C16 C17 C18 C13 0.8(7) . . . . ? C14 C13 C18 F5 178.4(4) . . . . ? C1 C13 C18 F5 -0.2(6) . . . . ? C14 C13 C18 C17 -0.1(6) . . . . ? C1 C13 C18 C17 -178.7(4) . . . . ? C7 C8 C19 C24 172.7(3) . . . . ? S2 C8 C19 C24 -8.3(4) . . . . ? C7 C8 C19 C20 -8.6(5) . . . . ? S2 C8 C19 C20 170.4(3) . . . . ? C24 C19 C20 F6 177.8(3) . . . . ? C8 C19 C20 F6 -1.1(5) . . . . ? C24 C19 C20 C21 0.3(5) . . . . ? C8 C19 C20 C21 -178.5(3) . . . . ? F6 C20 C21 F7 0.0(5) . . . . ? C19 C20 C21 F7 177.5(3) . . . . ? F6 C20 C21 C22 -178.7(3) . . . . ? C19 C20 C21 C22 -1.1(6) . . . . ? F7 C21 C22 F8 2.3(5) . . . . ? C20 C21 C22 F8 -179.1(3) . . . . ? F7 C21 C22 C23 -177.7(3) . . . . ? C20 C21 C22 C23 0.9(6) . . . . ? F8 C22 C23 F9 -0.1(6) . . . . ? C21 C22 C23 F9 179.9(3) . . . . ? F8 C22 C23 C24 180.0(3) . . . . ? C21 C22 C23 C24 0.0(6) . . . . ? F9 C23 C24 F10 -0.5(5) . . . . ? C22 C23 C24 F10 179.4(3) . . . . ? F9 C23 C24 C19 179.2(3) . . . . ? C22 C23 C24 C19 -0.9(6) . . . . ? C20 C19 C24 F10 -179.6(3) . . . . ? C8 C19 C24 F10 -0.8(5) . . . . ? C20 C19 C24 C23 0.7(5) . . . . ? C8 C19 C24 C23 179.5(3) . . . . ? C4A S1A C1A C2A -1.3(3) . . . . ? C4A S1A C1A C13A 177.9(3) . . . . ? C13A C1A C2A C3A -177.8(3) . . . . ? S1A C1A C2A C3A 1.3(4) . . . . ? C1A C2A C3A C4A -0.7(4) . . . . ? C1A C2A C3A C9A -178.7(4) . . . . ? C2A C3A C4A C5A -179.9(3) . . . . ? C9A C3A C4A C5A -1.3(4) . . . . ? C2A C3A C4A S1A -0.3(4) . . . . ? C9A C3A C4A S1A 178.3(2) . . . . ? C1A S1A C4A C3A 0.9(3) . . . . ? C1A S1A C4A C5A -179.7(4) . . . . ? C3A C4A C5A C6A 1.2(4) . . . . ? S1A C4A C5A C6A -178.2(3) . . . . ? C3A C4A C5A S2A -176.7(3) . . . . ? S1A C4A C5A S2A 3.9(6) . . . . ? C8A S2A C5A C6A 0.0(3) . . . . ? C8A S2A C5A C4A 177.9(4) . . . . ? C4A C5A C6A C7A -179.1(3) . . . . ? S2A C5A C6A C7A -0.6(4) . . . . ? C4A C5A C6A C9A -0.7(4) . . . . ? S2A C5A C6A C9A 177.8(2) . . . . ? C5A C6A C7A C8A 1.1(4) . . . . ? C9A C6A C7A C8A -176.7(4) . . . . ? C6A C7A C8A C19A 177.6(3) . . . . ? C6A C7A C8A S2A -1.1(4) . . . . ? C5A S2A C8A C7A 0.6(3) . . . . ? C5A S2A C8A C19A -178.1(3) . . . . ? C5A C6A C9A C10A 179.8(3) . . . . ? C7A C6A C9A C10A -2.3(7) . . . . ? C5A C6A C9A C3A -0.1(4) . . . . ? C7A C6A C9A C3A 177.8(4) . . . . ? C4A C3A C9A C10A -179.1(3) . . . . ? C2A C3A C9A C10A -1.0(7) . . . . ? C4A C3A C9A C6A 0.8(3) . . . . ? C2A C3A C9A C6A 178.9(4) . . . . ? C6A C9A C10A C11A 177.2(3) . . . . ? C3A C9A C10A C11A -2.9(6) . . . . ? C6A C9A C10A C12A -2.1(6) . . . . ? C3A C9A C10A C12A 177.8(3) . . . . ? C2A C1A C13A C14A -157.8(3) . . . . ? S1A C1A C13A C14A 23.2(5) . . . . ? C2A C1A C13A C18A 21.2(5) . . . . ? S1A C1A C13A C18A -157.7(3) . . . . ? C18A C13A C14A F1A 178.5(3) . . . . ? C1A C13A C14A F1A -2.4(5) . . . . ? C18A C13A C14A C15A -2.6(5) . . . . ? C1A C13A C14A C15A 176.5(3) . . . . ? F1A C14A C15A F2A 1.5(5) . . . . ? C13A C14A C15A F2A -177.4(3) . . . . ? F1A C14A C15A C16A -178.1(3) . . . . ? C13A C14A C15A C16A 2.9(6) . . . . ? F2A C15A C16A F3A -0.2(6) . . . . ? C14A C15A C16A F3A 179.4(3) . . . . ? F2A C15A C16A C17A 179.1(3) . . . . ? C14A C15A C16A C17A -1.3(6) . . . . ? F3A C16A C17A F4A -0.6(6) . . . . ? C15A C16A C17A F4A -179.9(4) . . . . ? F3A C16A C17A C18A 178.8(3) . . . . ? C15A C16A C17A C18A -0.4(6) . . . . ? F4A C17A C18A F5A -0.1(6) . . . . ? C16A C17A C18A F5A -179.5(4) . . . . ? F4A C17A C18A C13A -179.9(4) . . . . ? C16A C17A C18A C13A 0.7(6) . . . . ? C14A C13A C18A F5A -179.0(3) . . . . ? C1A C13A C18A F5A 1.8(5) . . . . ? C14A C13A C18A C17A 0.8(6) . . . . ? C1A C13A C18A C17A -178.4(4) . . . . ? C7A C8A C19A C24A 175.8(3) . . . . ? S2A C8A C19A C24A -5.7(5) . . . . ? C7A C8A C19A C20A -6.9(5) . . . . ? S2A C8A C19A C20A 171.6(3) . . . . ? C24A C19A C20A F6A 179.8(3) . . . . ? C8A C19A C20A F6A 2.2(5) . . . . ? C24A C19A C20A C21A -0.7(5) . . . . ? C8A C19A C20A C21A -178.2(3) . . . . ? F6A C20A C21A F7A -0.2(6) . . . . ? C19A C20A C21A F7A -179.7(4) . . . . ? F6A C20A C21A C22A 179.5(4) . . . . ? C19A C20A C21A C22A 0.0(6) . . . . ? F7A C21A C22A F8A -1.0(6) . . . . ? C20A C21A C22A F8A 179.3(4) . . . . ? F7A C21A C22A C23A 180.0(4) . . . . ? C20A C21A C22A C23A 0.3(6) . . . . ? F8A C22A C23A F9A -0.2(6) . . . . ? C21A C22A C23A F9A 178.8(3) . . . . ? F8A C22A C23A C24A -178.8(3) . . . . ? C21A C22A C23A C24A 0.2(6) . . . . ? F9A C23A C24A F10A 0.5(5) . . . . ? C22A C23A C24A F10A 179.1(3) . . . . ? F9A C23A C24A C19A -179.6(3) . . . . ? C22A C23A C24A C19A -1.0(6) . . . . ? C20A C19A C24A F10A -179.0(3) . . . . ? C8A C19A C24A F10A -1.4(5) . . . . ? C20A C19A C24A C23A 1.2(5) . . . . ? C8A C19A C24A C23A 178.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.204 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.046 #===END #Compound 7 data_js15 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H11 F5 O2 S2' _chemical_formula_weight 478.44 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3262(3) _cell_length_b 9.9514(4) _cell_length_c 12.7866(5) _cell_angle_alpha 112.274(2) _cell_angle_beta 99.195(2) _cell_angle_gamma 91.288(3) _cell_volume 963.80(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.344 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6187 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3384 _reflns_number_gt 2585 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.3832P] 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 3384 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0988 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 S1 S 0.26483(8) 0.53078(7) 0.60832(5) 0.04566(19) Uani 1 1 d . . . S2 S 0.44540(8) 0.16039(7) 0.42174(6) 0.04624(19) Uani 1 1 d . . . F1 F 0.2509(2) 0.74965(19) 0.81586(13) 0.0633(5) Uani 1 1 d . . . F2 F 0.1606(2) 0.9884(2) 0.96616(14) 0.0811(6) Uani 1 1 d . . . F3 F -0.0312(3) 1.16826(19) 0.89430(16) 0.0824(6) Uani 1 1 d . . . F4 F -0.1290(2) 1.09801(17) 0.66602(16) 0.0707(5) Uani 1 1 d . . . F5 F -0.0473(2) 0.85805(17) 0.51311(13) 0.0607(4) Uani 1 1 d . . . O1 O 0.0981(2) 0.3732(2) 0.19605(16) 0.0554(5) Uani 1 1 d . . . O2 O 0.3490(2) 0.4898(2) 0.23259(16) 0.0553(5) Uani 1 1 d . . . C1 C 0.1655(3) 0.6630(3) 0.5704(2) 0.0405(6) Uani 1 1 d . . . C2 C 0.1554(3) 0.6323(3) 0.4550(2) 0.0437(6) Uani 1 1 d . . . H2 H 0.1078 0.6905 0.4186 0.052 Uiso 1 1 calc R . . C3 C 0.2249(3) 0.5037(3) 0.3984(2) 0.0414(6) Uani 1 1 d . . . C4 C 0.2873(3) 0.4369(3) 0.4701(2) 0.0404(5) Uani 1 1 d . . . C5 C 0.3508(3) 0.3017(3) 0.4022(2) 0.0402(6) Uani 1 1 d . . . C6 C 0.3265(3) 0.2854(3) 0.2894(2) 0.0406(6) Uani 1 1 d . . . C7 C 0.3834(3) 0.1592(3) 0.2170(2) 0.0436(6) Uani 1 1 d . . . H7 H 0.3764 0.1337 0.1384 0.052 Uiso 1 1 calc R . . C8 C 0.4513(3) 0.0765(3) 0.2751(2) 0.0419(6) Uani 1 1 d . . . C9 C 0.2474(3) 0.4148(3) 0.2753(2) 0.0426(6) Uani 1 1 d . . . C10 C 0.0809(5) 0.4790(4) 0.1474(3) 0.0843(11) Uani 1 1 d . . . H10A H -0.0014 0.5428 0.1778 0.101 Uiso 1 1 calc R . . H10B H 0.0487 0.4325 0.0646 0.101 Uiso 1 1 calc R . . C11 C 0.2435(5) 0.5635(4) 0.1789(3) 0.0711(9) Uani 1 1 d . . . H11A H 0.2803 0.5646 0.1110 0.085 Uiso 1 1 calc R . . H11B H 0.2386 0.6632 0.2313 0.085 Uiso 1 1 calc R . . C12 C 0.1103(3) 0.7916(3) 0.6560(2) 0.0409(6) Uani 1 1 d . . . C13 C 0.1554(3) 0.8319(3) 0.7741(2) 0.0483(6) Uani 1 1 d . . . C14 C 0.1088(4) 0.9564(3) 0.8538(2) 0.0559(7) Uani 1 1 d . . . C15 C 0.0131(4) 1.0452(3) 0.8182(3) 0.0566(7) Uani 1 1 d . . . C16 C -0.0365(3) 1.0099(3) 0.7029(2) 0.0513(7) Uani 1 1 d . . . C17 C 0.0099(3) 0.8853(3) 0.6245(2) 0.0457(6) Uani 1 1 d . . . C18 C 0.5219(3) -0.0636(3) 0.2281(2) 0.0436(6) Uani 1 1 d . . . C19 C 0.4956(4) -0.1434(3) 0.1105(2) 0.0564(7) Uani 1 1 d . . . H19 H 0.4315 -0.1085 0.0614 0.068 Uiso 1 1 calc R . . C20 C 0.5633(4) -0.2744(3) 0.0649(3) 0.0642(8) Uani 1 1 d . . . H20 H 0.5464 -0.3256 -0.0143 0.077 Uiso 1 1 calc R . . C21 C 0.6552(4) -0.3288(3) 0.1364(3) 0.0663(8) Uani 1 1 d . . . H21 H 0.6989 -0.4176 0.1058 0.080 Uiso 1 1 calc R . . C22 C 0.6823(4) -0.2515(3) 0.2530(3) 0.0637(8) Uani 1 1 d . . . H22 H 0.7451 -0.2883 0.3014 0.076 Uiso 1 1 calc R . . C23 C 0.6172(4) -0.1195(3) 0.2995(3) 0.0544(7) Uani 1 1 d . . . H23 H 0.6371 -0.0678 0.3787 0.065 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0510(4) 0.0445(4) 0.0431(4) 0.0184(3) 0.0086(3) 0.0107(3) S2 0.0523(4) 0.0450(4) 0.0456(4) 0.0212(3) 0.0099(3) 0.0136(3) F1 0.0581(10) 0.0809(11) 0.0491(9) 0.0240(8) 0.0061(7) 0.0204(9) F2 0.0774(12) 0.1041(15) 0.0422(10) 0.0067(9) 0.0089(9) 0.0194(11) F3 0.1006(15) 0.0598(10) 0.0707(12) 0.0006(9) 0.0313(11) 0.0195(10) F4 0.0940(13) 0.0479(9) 0.0814(12) 0.0296(9) 0.0330(10) 0.0281(9) F5 0.0814(12) 0.0553(9) 0.0503(9) 0.0236(7) 0.0146(8) 0.0268(9) O1 0.0557(12) 0.0560(11) 0.0514(11) 0.0227(9) -0.0042(9) 0.0071(9) O2 0.0636(12) 0.0524(11) 0.0655(12) 0.0345(10) 0.0243(10) 0.0136(9) C1 0.0403(13) 0.0370(12) 0.0434(14) 0.0154(11) 0.0054(11) 0.0031(11) C2 0.0465(14) 0.0397(13) 0.0477(15) 0.0198(11) 0.0087(11) 0.0086(11) C3 0.0412(14) 0.0392(13) 0.0444(14) 0.0171(11) 0.0074(11) 0.0049(11) C4 0.0387(13) 0.0383(12) 0.0442(14) 0.0160(11) 0.0070(11) 0.0047(11) C5 0.0391(13) 0.0379(13) 0.0455(14) 0.0185(11) 0.0070(11) 0.0049(11) C6 0.0404(13) 0.0390(13) 0.0448(14) 0.0195(11) 0.0062(11) 0.0047(11) C7 0.0468(14) 0.0415(13) 0.0425(14) 0.0163(11) 0.0080(11) 0.0052(11) C8 0.0415(14) 0.0395(13) 0.0449(14) 0.0163(11) 0.0086(11) 0.0033(11) C9 0.0470(14) 0.0409(13) 0.0426(14) 0.0186(11) 0.0088(11) 0.0080(11) C10 0.101(3) 0.078(2) 0.081(2) 0.047(2) -0.007(2) 0.022(2) C11 0.094(3) 0.0646(19) 0.080(2) 0.0467(18) 0.037(2) 0.0342(19) C12 0.0390(13) 0.0382(13) 0.0446(14) 0.0141(11) 0.0103(11) 0.0012(11) C13 0.0410(14) 0.0527(15) 0.0495(15) 0.0180(13) 0.0081(12) 0.0037(12) C14 0.0520(16) 0.0617(18) 0.0438(16) 0.0087(13) 0.0107(13) -0.0011(14) C15 0.0607(18) 0.0427(15) 0.0566(18) 0.0037(13) 0.0224(14) 0.0042(14) C16 0.0561(17) 0.0376(13) 0.0627(18) 0.0198(13) 0.0169(14) 0.0068(12) C17 0.0527(15) 0.0392(13) 0.0465(15) 0.0171(12) 0.0118(12) 0.0023(12) C18 0.0433(14) 0.0376(13) 0.0526(15) 0.0193(12) 0.0120(12) 0.0051(11) C19 0.0628(18) 0.0491(15) 0.0559(17) 0.0190(13) 0.0085(14) 0.0142(14) C20 0.073(2) 0.0507(16) 0.0603(19) 0.0115(14) 0.0129(16) 0.0164(16) C21 0.068(2) 0.0450(16) 0.084(2) 0.0194(16) 0.0209(17) 0.0203(15) C22 0.070(2) 0.0552(17) 0.076(2) 0.0351(16) 0.0146(16) 0.0204(16) C23 0.0615(18) 0.0512(15) 0.0566(17) 0.0259(13) 0.0140(14) 0.0142(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 S1 C4 1.701(2) . ? S1 C1 1.748(2) . ? S2 C5 1.707(2) . ? S2 C8 1.749(2) . ? F1 C13 1.347(3) . ? F2 C14 1.341(3) . ? F3 C15 1.346(3) . ? F4 C16 1.346(3) . ? F5 C17 1.346(3) . ? O1 C10 1.410(3) . ? O1 C9 1.414(3) . ? O2 C9 1.413(3) . ? O2 C11 1.414(3) . ? C1 C2 1.376(3) . ? C1 C12 1.474(3) . ? C2 C3 1.400(3) . ? C2 H2 0.9300 . ? C3 C4 1.371(3) . ? C3 C9 1.530(3) . ? C4 C5 1.462(3) . ? C5 C6 1.369(3) . ? C6 C7 1.395(3) . ? C6 C9 1.517(3) . ? C7 C8 1.378(3) . ? C7 H7 0.9300 . ? C8 C18 1.472(3) . ? C10 C11 1.490(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.390(4) . ? C12 C17 1.395(3) . ? C13 C14 1.384(4) . ? C14 C15 1.358(4) . ? C15 C16 1.369(4) . ? C16 C17 1.377(4) . ? C18 C19 1.387(4) . ? C18 C23 1.395(4) . ? C19 C20 1.385(4) . ? C19 H19 0.9300 . ? C20 C21 1.373(4) . ? C20 H20 0.9300 . ? C21 C22 1.372(4) . ? C21 H21 0.9300 . ? C22 C23 1.385(4) . ? C22 H22 0.9300 . ? C23 H23 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 C4 S1 C1 91.13(11) . . ? C5 S2 C8 91.40(11) . . ? C10 O1 C9 106.3(2) . . ? C9 O2 C11 105.7(2) . . ? C2 C1 C12 127.0(2) . . ? C2 C1 S1 110.89(17) . . ? C12 C1 S1 122.04(18) . . ? C1 C2 C3 112.6(2) . . ? C1 C2 H2 123.7 . . ? C3 C2 H2 123.7 . . ? C4 C3 C2 113.0(2) . . ? C4 C3 C9 110.4(2) . . ? C2 C3 C9 136.6(2) . . ? C3 C4 C5 108.6(2) . . ? C3 C4 S1 112.44(17) . . ? C5 C4 S1 138.94(19) . . ? C6 C5 C4 109.4(2) . . ? C6 C5 S2 111.60(18) . . ? C4 C5 S2 139.02(19) . . ? C5 C6 C7 113.9(2) . . ? C5 C6 C9 110.4(2) . . ? C7 C6 C9 135.6(2) . . ? C8 C7 C6 112.3(2) . . ? C8 C7 H7 123.8 . . ? C6 C7 H7 123.8 . . ? C7 C8 C18 128.1(2) . . ? C7 C8 S2 110.75(17) . . ? C18 C8 S2 121.15(18) . . ? O2 C9 O1 105.98(19) . . ? O2 C9 C6 111.1(2) . . ? O1 C9 C6 112.6(2) . . ? O2 C9 C3 113.5(2) . . ? O1 C9 C3 112.7(2) . . ? C6 C9 C3 101.14(19) . . ? O1 C10 C11 106.4(3) . . ? O1 C10 H10A 110.5 . . ? C11 C10 H10A 110.5 . . ? O1 C10 H10B 110.5 . . ? C11 C10 H10B 110.5 . . ? H10A C10 H10B 108.6 . . ? O2 C11 C10 104.9(2) . . ? O2 C11 H11A 110.8 . . ? C10 C11 H11A 110.8 . . ? O2 C11 H11B 110.8 . . ? C10 C11 H11B 110.8 . . ? H11A C11 H11B 108.8 . . ? C13 C12 C17 114.2(2) . . ? C13 C12 C1 123.6(2) . . ? C17 C12 C1 122.2(2) . . ? F1 C13 C14 116.7(2) . . ? F1 C13 C12 120.1(2) . . ? C14 C13 C12 123.2(2) . . ? F2 C14 C15 120.7(2) . . ? F2 C14 C13 119.1(3) . . ? C15 C14 C13 120.1(3) . . ? F3 C15 C14 121.1(3) . . ? F3 C15 C16 119.7(3) . . ? C14 C15 C16 119.2(2) . . ? F4 C16 C15 120.0(2) . . ? F4 C16 C17 119.9(2) . . ? C15 C16 C17 120.1(2) . . ? F5 C17 C16 115.9(2) . . ? F5 C17 C12 120.9(2) . . ? C16 C17 C12 123.1(2) . . ? C19 C18 C23 118.2(2) . . ? C19 C18 C8 120.3(2) . . ? C23 C18 C8 121.5(2) . . ? C20 C19 C18 121.0(3) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C21 C20 C19 120.1(3) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C22 C21 C20 119.7(3) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C23 120.6(3) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 C18 120.3(3) . . ? C22 C23 H23 119.9 . . ? C18 C23 H23 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 -0.9(2) . . . . ? C4 S1 C1 C12 -178.2(2) . . . . ? C12 C1 C2 C3 177.8(2) . . . . ? S1 C1 C2 C3 0.7(3) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C1 C2 C3 C9 178.7(3) . . . . ? C2 C3 C4 C5 177.8(2) . . . . ? C9 C3 C4 C5 -1.1(3) . . . . ? C2 C3 C4 S1 -0.8(3) . . . . ? C9 C3 C4 S1 -179.75(18) . . . . ? C1 S1 C4 C3 1.0(2) . . . . ? C1 S1 C4 C5 -177.0(3) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? S1 C4 C5 C6 177.7(2) . . . . ? C3 C4 C5 S2 179.4(2) . . . . ? S1 C4 C5 S2 -2.5(5) . . . . ? C8 S2 C5 C6 -0.5(2) . . . . ? C8 S2 C5 C4 179.8(3) . . . . ? C4 C5 C6 C7 179.9(2) . . . . ? S2 C5 C6 C7 0.0(3) . . . . ? C4 C5 C6 C9 1.7(3) . . . . ? S2 C5 C6 C9 -178.13(17) . . . . ? C5 C6 C7 C8 0.6(3) . . . . ? C9 C6 C7 C8 178.1(3) . . . . ? C6 C7 C8 C18 179.2(2) . . . . ? C6 C7 C8 S2 -0.9(3) . . . . ? C5 S2 C8 C7 0.8(2) . . . . ? C5 S2 C8 C18 -179.3(2) . . . . ? C11 O2 C9 O1 33.6(3) . . . . ? C11 O2 C9 C6 156.2(2) . . . . ? C11 O2 C9 C3 -90.6(3) . . . . ? C10 O1 C9 O2 -29.3(3) . . . . ? C10 O1 C9 C6 -150.9(2) . . . . ? C10 O1 C9 C3 95.4(3) . . . . ? C5 C6 C9 O2 118.6(2) . . . . ? C7 C6 C9 O2 -59.0(4) . . . . ? C5 C6 C9 O1 -122.7(2) . . . . ? C7 C6 C9 O1 59.7(4) . . . . ? C5 C6 C9 C3 -2.2(3) . . . . ? C7 C6 C9 C3 -179.8(3) . . . . ? C4 C3 C9 O2 -117.1(2) . . . . ? C2 C3 C9 O2 64.3(4) . . . . ? C4 C3 C9 O1 122.4(2) . . . . ? C2 C3 C9 O1 -56.2(4) . . . . ? C4 C3 C9 C6 2.0(3) . . . . ? C2 C3 C9 C6 -176.6(3) . . . . ? C9 O1 C10 C11 13.7(3) . . . . ? C9 O2 C11 C10 -24.3(3) . . . . ? O1 C10 C11 O2 6.6(4) . . . . ? C2 C1 C12 C13 -165.5(3) . . . . ? S1 C1 C12 C13 11.3(4) . . . . ? C2 C1 C12 C17 13.1(4) . . . . ? S1 C1 C12 C17 -170.1(2) . . . . ? C17 C12 C13 F1 179.3(2) . . . . ? C1 C12 C13 F1 -2.0(4) . . . . ? C17 C12 C13 C14 -1.7(4) . . . . ? C1 C12 C13 C14 177.0(3) . . . . ? F1 C13 C14 F2 0.3(4) . . . . ? C12 C13 C14 F2 -178.7(3) . . . . ? F1 C13 C14 C15 179.7(3) . . . . ? C12 C13 C14 C15 0.7(4) . . . . ? F2 C14 C15 F3 0.7(4) . . . . ? C13 C14 C15 F3 -178.8(3) . . . . ? F2 C14 C15 C16 179.5(3) . . . . ? C13 C14 C15 C16 0.0(4) . . . . ? F3 C15 C16 F4 0.0(4) . . . . ? C14 C15 C16 F4 -178.8(3) . . . . ? F3 C15 C16 C17 179.2(3) . . . . ? C14 C15 C16 C17 0.4(4) . . . . ? F4 C16 C17 F5 -2.1(4) . . . . ? C15 C16 C17 F5 178.7(2) . . . . ? F4 C16 C17 C12 177.7(2) . . . . ? C15 C16 C17 C12 -1.5(4) . . . . ? C13 C12 C17 F5 -178.2(2) . . . . ? C1 C12 C17 F5 3.1(4) . . . . ? C13 C12 C17 C16 2.1(4) . . . . ? C1 C12 C17 C16 -176.6(2) . . . . ? C7 C8 C18 C19 -13.6(4) . . . . ? S2 C8 C18 C19 166.5(2) . . . . ? C7 C8 C18 C23 166.0(3) . . . . ? S2 C8 C18 C23 -14.0(4) . . . . ? C23 C18 C19 C20 -0.6(4) . . . . ? C8 C18 C19 C20 179.0(3) . . . . ? C18 C19 C20 C21 1.4(5) . . . . ? C19 C20 C21 C22 -1.2(5) . . . . ? C20 C21 C22 C23 0.3(5) . . . . ? C21 C22 C23 C18 0.5(5) . . . . ? C19 C18 C23 C22 -0.4(4) . . . . ? C8 C18 C23 C22 -179.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.191 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.040 #===END