# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_section_title ;Chemo- and Enantioselective Sulfoxidation of Bis(ethylenedithio)- Tetrathiafulvalene (BEDT-TTF) into Chiral BEDT-TTF-Sulfoxide ; _publ_contact_author_name 'Narcis Avarvari' _publ_contact_author_email NARCIS.AVARVARI@UNIV-ANGERS.FR loop_ _publ_author_name N.Avarvari M.Chas M.Gulea M.Lemarie data_2c _database_code_depnum_ccdc_archive 'CCDC 661107' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'BEDT-TTF-S-oxide, rac' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 O S8' _chemical_formula_weight 400.64 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 P21/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 6.581(3) _cell_length_b 28.674(2) _cell_length_c 8.284(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.91(3) _cell_angle_gamma 90.00 _cell_volume 1495.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 83 _cell_measurement_theta_min 4.51 _cell_measurement_theta_max 19.24 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.779 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 1.179 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.546 _exptl_absorpt_correction_T_max 0.678 _exptl_absorpt_process_details wingx _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 area_detector _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22487 _diffrn_reflns_av_R_equivalents 0.0891 _diffrn_reflns_av_sigmaI/netI 0.0835 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3431 _reflns_number_gt 1979 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'Denzo and Scalepak' _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^)+(0.0543P)^2^+1.8220P] 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 3431 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1239 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1380 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 -0.60413(19) 0.30484(4) 0.37578(19) 0.0580(4) Uani 1 1 d . . . S2 S -0.41059(16) 0.38138(4) 0.60409(16) 0.0379(3) Uani 1 1 d . . . S3 S -0.24121(18) 0.48659(4) 0.68803(19) 0.0487(4) Uani 1 1 d . . . S4 S -0.1297(2) 0.58647(4) 0.7486(3) 0.0891(7) Uani 1 1 d . . . S5 S 0.3847(2) 0.54914(5) 0.8236(3) 0.0891(7) Uani 1 1 d . . . S6 S 0.19753(18) 0.45535(4) 0.75277(19) 0.0499(4) Uani 1 1 d . . . S7 S 0.03406(17) 0.34891(4) 0.66418(15) 0.0356(3) Uani 1 1 d . . . S8 S -0.09379(19) 0.26529(4) 0.43882(17) 0.0455(3) Uani 1 1 d . . . O1 O 0.0814(7) 0.32636(14) 0.8335(5) 0.0560(12) Uani 0.80 1 d P . . O2 O -0.458(2) 0.3653(5) 0.755(2) 0.039(4) Uani 0.20 1 d P . . C1 C -0.5293(8) 0.24580(17) 0.3420(7) 0.0533(14) Uani 1 1 d . . . H1A H -0.6353 0.2249 0.3623 0.064 Uiso 1 1 calc R . . H1B H -0.5355 0.2427 0.2240 0.064 Uiso 1 1 calc R . . C2 C -0.3710(6) 0.33069(13) 0.4967(5) 0.0333(10) Uani 1 1 d . . . C3 C -0.1406(6) 0.39623(13) 0.6546(5) 0.0311(10) Uani 1 1 d . . . C4 C -0.0701(6) 0.44042(14) 0.6909(5) 0.0304(10) Uani 1 1 d . . . C5 C -0.0444(7) 0.52940(14) 0.7412(7) 0.0451(13) Uani 1 1 d . . . C6 C 0.0958(9) 0.6140(2) 0.8673(10) 0.089(2) Uani 1 1 d . . . H6A H 0.0829 0.6462 0.8294 0.107 Uiso 1 1 calc R . . H6B H 0.0856 0.6145 0.9818 0.107 Uiso 1 1 calc R . . C7 C 0.3011(9) 0.6012(2) 0.8805(12) 0.113(3) Uani 1 1 d . . . H7A H 0.3792 0.6054 0.9984 0.136 Uiso 1 1 calc R . . H7B H 0.3541 0.6247 0.8189 0.136 Uiso 1 1 calc R . . C8 C 0.1567(7) 0.51514(14) 0.7681(7) 0.0433(12) Uani 1 1 d . . . C9 C -0.1701(6) 0.31644(14) 0.5208(5) 0.0332(10) Uani 1 1 d . . . C10 C -0.3160(8) 0.22932(15) 0.4457(7) 0.0500(13) Uani 1 1 d . . . H10A H -0.2932 0.1982 0.4085 0.060 Uiso 1 1 calc R . . H10B H -0.3175 0.2270 0.5622 0.060 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 0.0387(7) 0.0358(7) 0.0834(11) -0.0104(7) -0.0074(7) -0.0061(5) S2 0.0276(5) 0.0272(6) 0.0583(8) -0.0061(5) 0.0113(5) -0.0005(4) S3 0.0289(6) 0.0243(6) 0.0896(10) -0.0100(6) 0.0122(6) -0.0011(5) S4 0.0438(8) 0.0258(7) 0.1762(19) -0.0225(9) -0.0019(10) 0.0037(6) S5 0.0377(8) 0.0477(8) 0.182(2) -0.0471(10) 0.0329(10) -0.0170(6) S6 0.0290(6) 0.0282(6) 0.0876(11) -0.0137(6) 0.0090(6) -0.0011(5) S7 0.0291(6) 0.0251(5) 0.0500(8) -0.0034(5) 0.0074(5) 0.0010(4) S8 0.0432(7) 0.0356(6) 0.0601(9) -0.0165(6) 0.0187(6) -0.0009(5) O1 0.063(3) 0.043(2) 0.055(3) 0.004(2) 0.006(2) 0.010(2) O2 0.037(8) 0.033(8) 0.051(10) -0.005(7) 0.020(8) 0.005(7) C1 0.053(3) 0.046(3) 0.062(4) -0.021(3) 0.019(3) -0.019(2) C2 0.035(2) 0.025(2) 0.038(3) -0.002(2) 0.006(2) -0.0078(18) C3 0.026(2) 0.026(2) 0.038(3) -0.0025(19) 0.0046(19) -0.0002(17) C4 0.031(2) 0.028(2) 0.031(3) 0.0029(19) 0.0052(19) 0.0005(18) C5 0.033(2) 0.020(2) 0.078(4) -0.007(2) 0.010(2) -0.0042(18) C6 0.060(4) 0.065(4) 0.134(6) -0.044(4) 0.016(4) 0.001(3) C7 0.047(4) 0.069(4) 0.206(9) -0.062(5) 0.009(5) -0.009(3) C8 0.033(2) 0.031(2) 0.064(3) -0.009(2) 0.011(2) -0.0044(19) C9 0.031(2) 0.027(2) 0.041(3) -0.003(2) 0.009(2) -0.0021(18) C10 0.064(3) 0.025(2) 0.066(4) -0.011(2) 0.027(3) -0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.736(4) . ? S1 C1 1.807(5) . ? S2 O2 1.445(15) . ? S2 C3 1.755(4) . ? S2 C2 1.763(4) . ? S3 C4 1.733(4) . ? S3 C5 1.745(4) . ? S4 C6 1.716(6) . ? S4 C5 1.737(4) . ? S5 C7 1.703(6) . ? S5 C8 1.736(4) . ? S6 C4 1.739(4) . ? S6 C8 1.746(4) . ? S7 O1 1.492(4) . ? S7 C3 1.765(4) . ? S7 C9 1.776(4) . ? S8 C9 1.750(4) . ? S8 C10 1.804(5) . ? C1 C10 1.494(7) . ? C2 C9 1.342(6) . ? C3 C4 1.353(5) . ? C5 C8 1.340(6) . ? C6 C7 1.373(8) . ? 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 C2 S1 C1 104.7(2) . . ? O2 S2 C3 109.1(6) . . ? O2 S2 C2 105.8(6) . . ? C3 S2 C2 91.86(19) . . ? C4 S3 C5 95.9(2) . . ? C6 S4 C5 102.7(3) . . ? C7 S5 C8 104.0(3) . . ? C4 S6 C8 95.68(19) . . ? O1 S7 C3 109.3(2) . . ? O1 S7 C9 108.2(2) . . ? C3 S7 C9 90.97(19) . . ? C9 S8 C10 98.1(2) . . ? C10 C1 S1 117.4(3) . . ? C9 C2 S1 128.5(3) . . ? C9 C2 S2 117.4(3) . . ? S1 C2 S2 114.1(2) . . ? C4 C3 S2 122.6(3) . . ? C4 C3 S7 122.2(3) . . ? S2 C3 S7 115.2(2) . . ? C3 C4 S3 122.2(3) . . ? C3 C4 S6 123.3(3) . . ? S3 C4 S6 114.5(2) . . ? C8 C5 S4 126.5(3) . . ? C8 C5 S3 116.9(3) . . ? S4 C5 S3 116.6(3) . . ? C7 C6 S4 126.1(5) . . ? C6 C7 S5 127.0(5) . . ? C5 C8 S5 127.5(3) . . ? C5 C8 S6 116.9(3) . . ? S5 C8 S6 115.6(3) . . ? C2 C9 S8 125.4(3) . . ? C2 C9 S7 117.4(3) . . ? S8 C9 S7 116.9(2) . . ? C1 C10 S8 115.8(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.141 _refine_diff_density_min -0.879 _refine_diff_density_rms 0.089 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 661108' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (BEDT-TTF-bis(sulfoxide))(TCNQF4) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H8 F4 N4 O2 S8' _chemical_formula_weight 692.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 26.776(4) _cell_length_b 9.890(3) _cell_length_c 10.644(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.44(3) _cell_angle_gamma 90.00 _cell_volume 2641.2(1) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 113 _cell_measurement_theta_min 4.4 _cell_measurement_theta_max 20.4 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.742 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.737 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76995 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type area_detector _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16031 _diffrn_reflns_av_R_equivalents 0.0568 _diffrn_reflns_av_sigmaI/netI 0.0700 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5001 _reflns_number_gt 3398 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'Denzo and Scalepak' _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^)+(0.0459P)^2^+0.3008P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.52(8) _refine_ls_number_reflns 5001 _refine_ls_number_parameters 364 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.0996 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.020 _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 0.55918(5) 0.26381(18) 0.80226(16) 0.0741(5) Uani 1 1 d . . . S2 S 0.53314(5) 0.53360(15) 0.57204(13) 0.0576(4) Uani 1 1 d . . . S3 S 0.44425(5) 0.28340(12) 0.75442(12) 0.0440(3) Uani 1 1 d . . . S4 S 0.42368(4) 0.51200(12) 0.56831(12) 0.0406(3) Uani 1 1 d . . . S5 S 0.32070(4) 0.28579(12) 0.73420(12) 0.0454(3) Uani 1 1 d . . . S6 S 0.29888(5) 0.51234(13) 0.54538(12) 0.0415(3) Uani 1 1 d . . . S7 S 0.21525(5) 0.27480(15) 0.75724(14) 0.0571(4) Uani 1 1 d . . . S8 S 0.18654(5) 0.54224(15) 0.52345(12) 0.0543(4) Uani 1 1 d . . . O1A O 0.3175(2) 0.1522(5) 0.6695(6) 0.0478(16) Uani 0.50 1 d P . . O1B O 0.3470(2) 0.2914(6) 0.8686(6) 0.0433(15) Uiso 0.50 1 d P . . O2A O 0.4464(3) 0.2864(7) 0.8882(7) 0.0603(18) Uiso 0.50 1 d P . . O2B O 0.4320(3) 0.1538(8) 0.6858(7) 0.072(2) Uiso 0.50 1 d P . . C1 C 0.5982(2) 0.3245(8) 0.7088(8) 0.093(2) Uani 1 1 d . . . H1A H 0.6351 0.2997 0.7564 0.112 Uiso 1 1 calc R . . H1B H 0.5869 0.2779 0.6233 0.112 Uiso 1 1 calc R . . C2 C 0.59621(19) 0.4741(8) 0.6820(7) 0.090(2) Uani 1 1 d . . . H2A H 0.6231 0.4963 0.6435 0.108 Uiso 1 1 calc R . . H2B H 0.6052 0.5218 0.7667 0.108 Uiso 1 1 calc R . . C3 C 0.49852(17) 0.3488(5) 0.7228(5) 0.0478(13) Uani 1 1 d . . . C4 C 0.48861(17) 0.4528(5) 0.6341(5) 0.0439(12) Uani 1 1 d . . . C5 C 0.39815(16) 0.4009(4) 0.6575(4) 0.0343(10) Uani 1 1 d . . . C6 C 0.34676(17) 0.4012(4) 0.6487(4) 0.0347(10) Uani 1 1 d . . . C7 C 0.25695(16) 0.3544(5) 0.6860(4) 0.0376(11) Uani 1 1 d . . . C8 C 0.24667(17) 0.4568(5) 0.5983(4) 0.0373(11) Uani 1 1 d . . . C9 C 0.1524(2) 0.3396(6) 0.6532(6) 0.0739(18) Uani 1 1 d . . . H9A H 0.1420 0.2951 0.5666 0.089 Uiso 1 1 calc R . . H9B H 0.1259 0.3176 0.6931 0.089 Uiso 1 1 calc R . . C10 C 0.1523(2) 0.4865(6) 0.6327(6) 0.0697(17) Uani 1 1 d . . . H10A H 0.1686 0.5297 0.7193 0.084 Uiso 1 1 calc R . . H10B H 0.1156 0.5171 0.5961 0.084 Uiso 1 1 calc R . . F1 F 0.85302(10) 0.2313(3) 0.8680(3) 0.0636(8) Uani 1 1 d . . . F2 F 0.95228(10) 0.2360(3) 0.8753(3) 0.0649(8) Uani 1 1 d . . . F3 F 0.79928(11) 0.4704(3) 0.4572(3) 0.0573(8) Uani 1 1 d . . . F4 F 0.89748(10) 0.4777(3) 0.4655(3) 0.0551(8) Uani 1 1 d . . . N1 N 0.73540(18) 0.2494(5) 0.8384(5) 0.0667(13) Uani 1 1 d . . . N2 N 0.6905(2) 0.4777(5) 0.4924(5) 0.0853(17) Uani 1 1 d . . . N3 N 1.06601(18) 0.2736(5) 0.8622(5) 0.0754(15) Uani 1 1 d . . . N4 N 1.0142(2) 0.4806(6) 0.5069(6) 0.0864(17) Uani 1 1 d . . . C11 C 0.82163(16) 0.3550(4) 0.6663(4) 0.0363(10) Uani 1 1 d . . . C12 C 0.86437(19) 0.2931(5) 0.7704(4) 0.0405(11) Uani 1 1 d . . . C13 C 0.91493(16) 0.2956(5) 0.7746(4) 0.0394(11) Uani 1 1 d . . . C14 C 0.93045(16) 0.3609(4) 0.6730(4) 0.0358(10) Uani 1 1 d . . . C15 C 0.88748(17) 0.4186(4) 0.5667(4) 0.0354(10) Uani 1 1 d . . . C16 C 0.83681(18) 0.4153(4) 0.5626(4) 0.0376(11) Uani 1 1 d . . . C17 C 0.76970(17) 0.3583(4) 0.6654(4) 0.0389(11) Uani 1 1 d . . . C18 C 0.75318(18) 0.2950(5) 0.7655(5) 0.0473(12) Uani 1 1 d . . . C19 C 0.7266(2) 0.4257(5) 0.5666(5) 0.0523(13) Uani 1 1 d . . . C20 C 0.98280(17) 0.3665(5) 0.6782(4) 0.0394(11) Uani 1 1 d . . . C21 C 1.0275(2) 0.3128(5) 0.7844(6) 0.0521(13) Uani 1 1 d . . . C22 C 0.99866(18) 0.4309(6) 0.5808(5) 0.0537(14) 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 0.0362(8) 0.1149(14) 0.0681(10) 0.0334(9) 0.0144(7) 0.0283(8) S2 0.0366(8) 0.0800(11) 0.0572(9) 0.0060(7) 0.0178(6) -0.0071(7) S3 0.0349(7) 0.0471(8) 0.0482(8) 0.0080(6) 0.0123(5) 0.0076(6) S4 0.0318(7) 0.0414(7) 0.0489(7) 0.0069(6) 0.0144(6) 0.0021(5) S5 0.0378(8) 0.0445(8) 0.0557(8) 0.0109(6) 0.0183(7) 0.0040(5) S6 0.0311(6) 0.0431(8) 0.0509(7) 0.0111(6) 0.0150(5) 0.0045(5) S7 0.0449(8) 0.0740(10) 0.0589(9) 0.0138(7) 0.0262(7) -0.0034(7) S8 0.0358(7) 0.0775(10) 0.0506(8) 0.0135(7) 0.0166(6) 0.0148(7) O1A 0.058(4) 0.018(3) 0.071(4) -0.013(3) 0.026(3) -0.004(3) C1 0.047(4) 0.122(6) 0.116(6) 0.004(5) 0.034(4) 0.023(4) C2 0.030(3) 0.133(7) 0.103(5) 0.018(4) 0.018(3) 0.001(4) C3 0.026(2) 0.066(4) 0.047(3) 0.001(3) 0.008(2) 0.009(2) C4 0.030(2) 0.055(3) 0.046(3) -0.005(3) 0.012(2) -0.002(2) C5 0.031(2) 0.038(3) 0.033(2) -0.001(2) 0.0108(19) 0.0010(19) C6 0.036(3) 0.032(3) 0.036(3) 0.002(2) 0.0128(19) 0.000(2) C7 0.031(2) 0.049(3) 0.037(3) 0.000(2) 0.016(2) -0.001(2) C8 0.032(2) 0.045(3) 0.036(3) -0.001(2) 0.014(2) 0.004(2) C9 0.044(3) 0.093(5) 0.077(4) 0.006(4) 0.011(3) -0.017(3) C10 0.042(3) 0.101(5) 0.078(4) 0.019(4) 0.035(3) 0.010(3) F1 0.0440(16) 0.091(2) 0.0576(18) 0.0332(17) 0.0204(14) 0.0051(15) F2 0.0387(16) 0.090(2) 0.0613(19) 0.0328(16) 0.0113(14) 0.0100(15) F3 0.0474(17) 0.073(2) 0.0465(17) 0.0161(15) 0.0101(14) 0.0097(14) F4 0.0521(18) 0.0708(19) 0.0443(17) 0.0134(14) 0.0194(14) -0.0016(14) N1 0.048(3) 0.091(3) 0.065(3) 0.010(3) 0.023(3) -0.004(2) N2 0.047(3) 0.118(4) 0.082(4) 0.021(3) 0.010(3) 0.019(3) N3 0.042(3) 0.112(4) 0.072(3) 0.007(3) 0.019(2) 0.015(3) N4 0.057(3) 0.126(5) 0.086(4) 0.020(3) 0.036(3) 0.000(3) C11 0.039(2) 0.031(3) 0.038(3) 0.000(2) 0.011(2) -0.005(2) C12 0.048(3) 0.039(3) 0.035(3) 0.009(2) 0.015(2) -0.001(2) C13 0.036(3) 0.046(3) 0.032(3) 0.011(2) 0.007(2) 0.003(2) C14 0.039(3) 0.033(3) 0.037(3) -0.009(2) 0.015(2) -0.004(2) C15 0.043(3) 0.038(3) 0.027(2) 0.001(2) 0.015(2) -0.004(2) C16 0.041(3) 0.033(3) 0.028(2) 0.005(2) -0.001(2) 0.006(2) C17 0.035(2) 0.042(3) 0.036(3) -0.001(2) 0.009(2) -0.001(2) C18 0.030(2) 0.054(3) 0.056(3) -0.007(3) 0.012(2) -0.003(2) C19 0.038(3) 0.066(4) 0.055(3) 0.000(3) 0.020(2) 0.001(3) C20 0.038(3) 0.044(3) 0.039(3) -0.002(2) 0.017(2) 0.001(2) C21 0.040(3) 0.064(4) 0.056(3) -0.002(3) 0.022(3) 0.001(3) C22 0.039(3) 0.075(4) 0.052(3) -0.001(3) 0.022(2) -0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C3 1.761(5) . ? S1 C1 1.780(7) . ? S2 C4 1.745(5) . ? S2 C2 1.785(5) . ? S3 O2A 1.406(7) . ? S3 O2B 1.455(8) . ? S3 C3 1.728(5) . ? S3 C5 1.746(4) . ? S4 C4 1.734(4) . ? S4 C5 1.740(4) . ? S5 O1B 1.357(6) . ? S5 O1A 1.479(5) . ? S5 C7 1.739(4) . ? S5 C6 1.750(4) . ? S6 C6 1.754(4) . ? S6 C8 1.768(5) . ? S7 C7 1.741(4) . ? S7 C9 1.780(5) . ? S8 C8 1.745(4) . ? S8 C10 1.801(6) . ? C1 C2 1.504(9) . ? C3 C4 1.358(6) . ? C5 C6 1.346(5) . ? C7 C8 1.339(6) . ? C9 C10 1.469(8) . ? F1 C12 1.329(5) . ? F2 C13 1.322(5) . ? F3 C16 1.334(5) . ? F4 C15 1.332(5) . ? N1 C18 1.136(6) . ? N2 C19 1.137(6) . ? N3 C21 1.141(6) . ? N4 C22 1.123(6) . ? C11 C17 1.388(6) . ? C11 C12 1.423(6) . ? C11 C16 1.432(6) . ? C12 C13 1.339(6) . ? C13 C14 1.440(6) . ? C14 C20 1.384(6) . ? C14 C15 1.421(6) . ? C15 C16 1.343(5) . ? C17 C19 1.425(7) . ? C17 C18 1.433(7) . ? C20 C22 1.404(7) . ? C20 C21 1.431(7) . ? 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 C3 S1 C1 101.2(3) . . ? C4 S2 C2 102.5(3) . . ? O2A S3 O2B 116.7(4) . . ? O2A S3 C3 116.8(3) . . ? O2B S3 C3 106.8(3) . . ? O2A S3 C5 110.8(3) . . ? O2B S3 C5 107.5(3) . . ? C3 S3 C5 96.0(2) . . ? C4 S4 C5 95.5(2) . . ? O1B S5 O1A 116.9(3) . . ? O1B S5 C7 112.9(3) . . ? O1A S5 C7 108.7(3) . . ? O1B S5 C6 111.6(3) . . ? O1A S5 C6 108.0(3) . . ? C7 S5 C6 96.9(2) . . ? C6 S6 C8 95.3(2) . . ? C7 S7 C9 100.2(2) . . ? C8 S8 C10 98.8(2) . . ? C2 C1 S1 116.7(5) . . ? C1 C2 S2 114.3(5) . . ? C4 C3 S3 116.5(3) . . ? C4 C3 S1 128.2(4) . . ? S3 C3 S1 115.2(3) . . ? C3 C4 S4 117.5(3) . . ? C3 C4 S2 128.0(3) . . ? S4 C4 S2 114.4(3) . . ? C6 C5 S4 123.2(3) . . ? C6 C5 S3 122.5(3) . . ? S4 C5 S3 114.3(2) . . ? C5 C6 S5 123.1(3) . . ? C5 C6 S6 123.4(3) . . ? S5 C6 S6 113.4(2) . . ? C8 C7 S5 116.3(3) . . ? C8 C7 S7 129.7(3) . . ? S5 C7 S7 114.1(3) . . ? C7 C8 S8 128.1(3) . . ? C7 C8 S6 117.7(3) . . ? S8 C8 S6 114.2(3) . . ? C10 C9 S7 113.6(4) . . ? C9 C10 S8 115.0(4) . . ? C17 C11 C12 123.2(4) . . ? C17 C11 C16 122.5(4) . . ? C12 C11 C16 114.3(4) . . ? F1 C12 C13 119.1(4) . . ? F1 C12 C11 117.7(4) . . ? C13 C12 C11 123.1(4) . . ? F2 C13 C12 119.3(4) . . ? F2 C13 C14 118.3(4) . . ? C12 C13 C14 122.5(4) . . ? C20 C14 C15 122.9(4) . . ? C20 C14 C13 122.8(4) . . ? C15 C14 C13 114.4(4) . . ? F4 C15 C16 118.1(4) . . ? F4 C15 C14 119.0(4) . . ? C16 C15 C14 122.9(4) . . ? F3 C16 C15 118.2(4) . . ? F3 C16 C11 119.0(4) . . ? C15 C16 C11 122.7(4) . . ? C11 C17 C19 124.5(4) . . ? C11 C17 C18 123.6(4) . . ? C19 C17 C18 111.9(4) . . ? N1 C18 C17 173.5(5) . . ? N2 C19 C17 175.9(6) . . ? C14 C20 C22 123.5(4) . . ? C14 C20 C21 125.0(4) . . ? C22 C20 C21 111.5(4) . . ? N3 C21 C20 173.6(6) . . ? N4 C22 C20 176.1(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.288 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.062