# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Ming-Chou Chen' _publ_contact_author_email MCCHEN@NCU.EDU.TW _publ_section_title ; One-Pot [1+1+1] Synthesis of Dithieno [2,3-b:3',2'-d]thiophene (DTT) and Their Fuctionalized Derivatives for Organic Thin-Film Transistors ; loop_ _publ_author_name 'Ming-Chou Chen.' 'Sheng-Yu Chen.' 'Yen-Ju Chiang.' 'Antonio Facchetti' ; Yue-Jhih Guo ; 'Tarng-Shiang Hu.' 'Choongik Kim.' 'Gene-Hsiang Lee.' ; You-jhih Liang ; 'Tobin Marks' # Attachment 'DB-DTT.cif' data_ic12547 _database_code_depnum_ccdc_archive 'CCDC 701639' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H12 O2 S3' _chemical_formula_weight 404.50 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 Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 11.6446(5) _cell_length_b 38.2970(17) _cell_length_c 3.8808(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1730.66(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used total _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.50 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.444 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8783 _exptl_absorpt_correction_T_max 0.9956 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8272 _diffrn_reflns_av_R_equivalents 0.0771 _diffrn_reflns_av_sigmaI/netI 0.0645 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -46 _diffrn_reflns_limit_k_max 49 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.06 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1976 _reflns_number_gt 1372 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.037(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1976 _refine_ls_number_parameters 125 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1353 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 0.24056(8) 0.2500 0.3123(3) 0.0262(3) Uani 1 2 d S . . S2 S -0.06236(6) 0.199341(17) 0.61079(18) 0.0264(3) Uani 1 1 d . . . O1 O -0.11638(16) 0.12842(5) 0.4505(6) 0.0394(6) Uani 1 1 d . . . C1 C 0.0372(2) 0.23134(7) 0.5312(6) 0.0237(6) Uani 1 1 d . . . C2 C 0.1410(2) 0.21769(6) 0.4164(6) 0.0234(6) Uani 1 1 d . . . C3 C 0.1407(2) 0.18087(6) 0.3934(6) 0.0250(6) Uani 1 1 d . . . H3 H 0.2045 0.1672 0.3212 0.030 Uiso 1 1 calc R . . C4 C 0.0361(2) 0.16740(6) 0.4893(7) 0.0256(6) Uani 1 1 d . . . C5 C -0.0111(2) 0.13177(7) 0.4693(7) 0.0270(6) Uani 1 1 d . . . C6 C 0.0644(2) 0.10051(7) 0.4741(7) 0.0263(6) Uani 1 1 d . . . C7 C 0.1726(2) 0.10075(7) 0.6261(7) 0.0269(6) Uani 1 1 d . . . H7 H 0.2023 0.1218 0.7212 0.032 Uiso 1 1 calc R . . C8 C 0.2368(3) 0.07049(7) 0.6387(7) 0.0314(7) Uani 1 1 d . . . H8 H 0.3103 0.0706 0.7449 0.038 Uiso 1 1 calc R . . C9 C 0.1943(3) 0.03994(7) 0.4968(7) 0.0351(7) Uani 1 1 d . . . H9 H 0.2392 0.0192 0.5032 0.042 Uiso 1 1 calc R . . C10 C 0.0862(3) 0.03944(7) 0.3452(7) 0.0344(7) Uani 1 1 d . . . H10 H 0.0572 0.0184 0.2489 0.041 Uiso 1 1 calc R . . C11 C 0.0215(3) 0.06937(7) 0.3346(7) 0.0305(7) Uani 1 1 d . . . H11 H -0.0526 0.0690 0.2325 0.037 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 0.0224(5) 0.0248(5) 0.0313(6) 0.000 0.0038(4) 0.000 S2 0.0222(4) 0.0275(4) 0.0294(4) 0.0015(3) 0.0021(3) -0.0004(3) O1 0.0226(11) 0.0349(11) 0.0607(15) 0.0000(10) 0.0014(10) -0.0038(9) C1 0.0220(14) 0.0288(14) 0.0204(13) 0.0013(11) 0.0018(11) -0.0003(11) C2 0.0229(15) 0.0269(14) 0.0203(14) 0.0020(11) 0.0023(11) -0.0030(11) C3 0.0240(14) 0.0274(14) 0.0237(14) 0.0007(11) 0.0007(12) 0.0022(12) C4 0.0259(15) 0.0274(14) 0.0236(14) 0.0014(11) -0.0016(12) 0.0009(11) C5 0.0263(15) 0.0289(15) 0.0256(14) 0.0015(11) 0.0008(12) -0.0034(12) C6 0.0280(16) 0.0278(14) 0.0230(14) 0.0026(11) 0.0042(12) -0.0039(12) C7 0.0280(15) 0.0287(15) 0.0241(15) 0.0013(12) 0.0020(12) -0.0037(12) C8 0.0314(16) 0.0356(16) 0.0274(15) 0.0040(12) 0.0019(13) 0.0015(13) C9 0.0421(19) 0.0317(17) 0.0316(16) 0.0039(13) 0.0075(15) 0.0084(14) C10 0.0467(19) 0.0264(15) 0.0303(16) -0.0008(12) 0.0059(14) -0.0063(13) C11 0.0299(16) 0.0343(15) 0.0273(15) 0.0007(12) 0.0004(13) -0.0068(13) _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 1.743(2) . ? S1 C2 1.743(2) 7_565 ? S2 C1 1.715(2) . ? S2 C4 1.741(3) . ? O1 C5 1.234(3) . ? C1 C2 1.390(3) . ? C1 C1 1.429(5) 7_565 ? C2 C3 1.413(3) . ? C3 C4 1.375(3) . ? C4 C5 1.474(3) . ? C5 C6 1.486(4) . ? C6 C7 1.391(4) . ? C6 C11 1.402(4) . ? C7 C8 1.380(4) . ? C8 C9 1.385(4) . ? C9 C10 1.389(4) . ? C10 C11 1.372(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C2 90.46(17) . 7_565 ? C1 S2 C4 90.46(13) . . ? C2 C1 C1 112.09(15) . 7_565 ? C2 C1 S2 112.14(19) . . ? C1 C1 S2 135.60(9) 7_565 . ? C1 C2 C3 113.2(2) . . ? C1 C2 S1 112.68(19) . . ? C3 C2 S1 134.1(2) . . ? C4 C3 C2 111.1(2) . . ? C3 C4 C5 131.6(2) . . ? C3 C4 S2 113.17(19) . . ? C5 C4 S2 114.78(19) . . ? O1 C5 C4 118.0(2) . . ? O1 C5 C6 120.3(2) . . ? C4 C5 C6 121.6(2) . . ? C7 C6 C11 119.5(3) . . ? C7 C6 C5 122.4(2) . . ? C11 C6 C5 118.0(2) . . ? C8 C7 C6 120.0(2) . . ? C7 C8 C9 120.1(3) . . ? C8 C9 C10 120.3(3) . . ? C11 C10 C9 119.9(3) . . ? C10 C11 C6 120.2(3) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.497 _refine_diff_density_min -0.538 _refine_diff_density_rms 0.152 # Attachment 'DFB-DTT.cif' data_ic12833 _database_code_depnum_ccdc_archive 'CCDC 701640' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H2 F10 O2 S3' _chemical_formula_weight 584.42 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 6.1883(3) _cell_length_b 9.3340(5) _cell_length_c 18.096(1) _cell_angle_alpha 103.105(1) _cell_angle_beta 97.954(1) _cell_angle_gamma 93.810(1) _cell_volume 1003.04(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3482 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 27.38 _exptl_crystal_description rod _exptl_crystal_colour light-yellow _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.935 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.485 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7279 _exptl_absorpt_correction_T_max 0.9531 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEXCCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13000 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4567 _reflns_number_gt 3787 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+0.6205P] 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 4567 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.0931 _refine_ls_wR_factor_gt 0.0884 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.53700(9) 0.81187(7) 1.00184(3) 0.02561(15) Uani 1 1 d . . . S2 S 1.14139(9) 0.66702(7) 1.06927(3) 0.02197(14) Uani 1 1 d . . . S3 S 1.07809(9) 0.82915(7) 0.88858(3) 0.02177(14) Uani 1 1 d . . . O1 O 1.2672(3) 0.5634(2) 1.20365(10) 0.0362(4) Uani 1 1 d . . . O2 O 1.0988(3) 0.9228(2) 0.75056(10) 0.0403(5) Uani 1 1 d . . . C1 C 0.9387(3) 0.7413(2) 1.02014(12) 0.0186(4) Uani 1 1 d . . . C2 C 0.7480(3) 0.7424(3) 1.05265(12) 0.0200(4) Uani 1 1 d . . . C3 C 0.7667(4) 0.6864(3) 1.11940(12) 0.0212(5) Uani 1 1 d . . . H3 H 0.6531 0.6806 1.1493 0.025 Uiso 1 1 calc R . . C4 C 0.9708(4) 0.6416(3) 1.13505(12) 0.0209(5) Uani 1 1 d . . . C5 C 1.0751(4) 0.5846(3) 1.19878(13) 0.0230(5) Uani 1 1 d . . . C6 C 0.9483(4) 0.5603(3) 1.26062(13) 0.0218(5) Uani 1 1 d . . . C7 C 0.7448(4) 0.4782(2) 1.24683(13) 0.0216(5) Uani 1 1 d . . . C8 C 0.6434(4) 0.4505(3) 1.30567(14) 0.0248(5) Uani 1 1 d . . . C9 C 0.7412(4) 0.5056(3) 1.38064(14) 0.0279(5) Uani 1 1 d . . . C10 C 0.9419(4) 0.5890(3) 1.39695(13) 0.0288(5) Uani 1 1 d . . . C11 C 1.0427(4) 0.6140(3) 1.33734(13) 0.0249(5) Uani 1 1 d . . . C12 C 0.9155(3) 0.7988(2) 0.95386(12) 0.0193(4) Uani 1 1 d . . . C13 C 0.7051(4) 0.8374(3) 0.93524(12) 0.0212(5) Uani 1 1 d . . . C14 C 0.6714(4) 0.8859(3) 0.86656(13) 0.0230(5) Uani 1 1 d . . . H14 H 0.5359 0.9130 0.8449 0.028 Uiso 1 1 calc R . . C15 C 0.8610(4) 0.8888(3) 0.83540(12) 0.0210(5) Uani 1 1 d . . . C16 C 0.9110(4) 0.9201(3) 0.76351(13) 0.0251(5) Uani 1 1 d . . . C17 C 0.7293(4) 0.9372(3) 0.70292(12) 0.0217(5) Uani 1 1 d . . . C18 C 0.7169(4) 0.8521(3) 0.62854(13) 0.0261(5) Uani 1 1 d . . . C19 C 0.5521(4) 0.8588(3) 0.57055(13) 0.0295(6) Uani 1 1 d . . . C20 C 0.3963(4) 0.9551(3) 0.58521(14) 0.0297(6) Uani 1 1 d . . . C21 C 0.4067(4) 1.0447(3) 0.65764(14) 0.0273(5) Uani 1 1 d . . . C22 C 0.5700(4) 1.0337(3) 0.71521(13) 0.0237(5) Uani 1 1 d . . . F1 F 0.6459(2) 0.42007(15) 1.17454(7) 0.0270(3) Uani 1 1 d . . . F2 F 0.4505(2) 0.36688(16) 1.29080(9) 0.0352(4) Uani 1 1 d . . . F3 F 0.6412(3) 0.47815(18) 1.43747(8) 0.0396(4) Uani 1 1 d . . . F4 F 1.0341(3) 0.64515(18) 1.46972(8) 0.0430(4) Uani 1 1 d . . . F5 F 1.2365(2) 0.69673(18) 1.35495(8) 0.0388(4) Uani 1 1 d . . . F6 F 0.8618(3) 0.75341(18) 0.61231(8) 0.0401(4) Uani 1 1 d . . . F7 F 0.5435(3) 0.77366(18) 0.49984(8) 0.0435(4) Uani 1 1 d . . . F8 F 0.2369(3) 0.96359(18) 0.52916(9) 0.0442(4) Uani 1 1 d . . . F9 F 0.2600(3) 1.14236(18) 0.67139(10) 0.0430(4) Uani 1 1 d . . . F10 F 0.5741(3) 1.12251(16) 0.78516(8) 0.0346(3) 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 0.0150(3) 0.0450(4) 0.0239(3) 0.0186(3) 0.0070(2) 0.0086(2) S2 0.0151(3) 0.0340(3) 0.0203(3) 0.0116(2) 0.0047(2) 0.0059(2) S3 0.0150(3) 0.0336(3) 0.0194(3) 0.0100(2) 0.0052(2) 0.0040(2) O1 0.0216(9) 0.0625(13) 0.0358(10) 0.0279(9) 0.0102(8) 0.0164(8) O2 0.0226(9) 0.0723(14) 0.0337(10) 0.0250(10) 0.0105(8) 0.0042(9) C1 0.0129(10) 0.0244(11) 0.0173(10) 0.0037(9) 0.0012(8) 0.0009(8) C2 0.0159(10) 0.0282(12) 0.0162(10) 0.0052(9) 0.0033(8) 0.0038(9) C3 0.0172(11) 0.0288(12) 0.0195(11) 0.0074(9) 0.0067(9) 0.0039(9) C4 0.0189(11) 0.0286(12) 0.0176(10) 0.0079(9) 0.0061(9) 0.0045(9) C5 0.0207(11) 0.0276(12) 0.0237(12) 0.0107(10) 0.0049(9) 0.0061(9) C6 0.0213(11) 0.0248(12) 0.0231(11) 0.0109(9) 0.0057(9) 0.0071(9) C7 0.0233(11) 0.0209(11) 0.0214(11) 0.0058(9) 0.0033(9) 0.0061(9) C8 0.0236(12) 0.0224(12) 0.0312(13) 0.0109(10) 0.0070(10) 0.0011(9) C9 0.0375(14) 0.0272(13) 0.0263(12) 0.0137(10) 0.0154(11) 0.0082(11) C10 0.0393(14) 0.0292(13) 0.0189(11) 0.0076(10) 0.0041(10) 0.0047(11) C11 0.0221(11) 0.0285(12) 0.0252(12) 0.0098(10) 0.0022(9) 0.0007(10) C12 0.0167(10) 0.0247(12) 0.0156(10) 0.0031(9) 0.0029(8) 0.0008(9) C13 0.0168(11) 0.0292(12) 0.0182(11) 0.0063(9) 0.0042(9) 0.0015(9) C14 0.0164(11) 0.0327(13) 0.0209(11) 0.0095(10) 0.0020(9) 0.0022(9) C15 0.0190(11) 0.0269(12) 0.0167(10) 0.0058(9) 0.0009(9) 0.0015(9) C16 0.0232(12) 0.0327(13) 0.0216(11) 0.0101(10) 0.0059(9) 0.0010(10) C17 0.0235(11) 0.0258(12) 0.0191(11) 0.0104(9) 0.0071(9) 0.0001(9) C18 0.0330(13) 0.0278(12) 0.0219(12) 0.0097(10) 0.0111(10) 0.0068(10) C19 0.0413(15) 0.0286(13) 0.0178(11) 0.0075(10) 0.0026(10) -0.0037(11) C20 0.0298(13) 0.0340(14) 0.0269(13) 0.0173(11) -0.0031(10) -0.0034(11) C21 0.0260(12) 0.0279(13) 0.0325(13) 0.0145(11) 0.0065(10) 0.0065(10) C22 0.0298(12) 0.0227(12) 0.0192(11) 0.0059(9) 0.0058(9) -0.0004(9) F1 0.0268(7) 0.0294(7) 0.0231(7) 0.0032(6) 0.0033(6) 0.0030(6) F2 0.0340(8) 0.0329(8) 0.0415(9) 0.0156(7) 0.0090(7) -0.0061(6) F3 0.0500(10) 0.0457(9) 0.0307(8) 0.0177(7) 0.0203(7) 0.0012(8) F4 0.0559(10) 0.0517(10) 0.0187(7) 0.0088(7) 0.0021(7) -0.0071(8) F5 0.0306(8) 0.0535(10) 0.0296(8) 0.0148(7) -0.0043(6) -0.0129(7) F6 0.0512(10) 0.0475(9) 0.0280(8) 0.0099(7) 0.0182(7) 0.0220(8) F7 0.0661(11) 0.0415(9) 0.0181(7) 0.0013(7) 0.0024(7) 0.0013(8) F8 0.0429(9) 0.0521(10) 0.0364(9) 0.0221(8) -0.0133(7) -0.0023(8) F9 0.0431(9) 0.0435(9) 0.0498(10) 0.0202(8) 0.0092(8) 0.0214(8) F10 0.0462(9) 0.0323(8) 0.0238(7) 0.0008(6) 0.0071(6) 0.0103(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 C2 1.738(2) . ? S1 C13 1.742(2) . ? S2 C1 1.712(2) . ? S2 C4 1.741(2) . ? S3 C12 1.712(2) . ? S3 C15 1.739(2) . ? O1 C5 1.213(3) . ? O2 C16 1.217(3) . ? C1 C2 1.389(3) . ? C1 C12 1.415(3) . ? C2 C3 1.415(3) . ? C3 C4 1.369(3) . ? C4 C5 1.465(3) . ? C5 C6 1.501(3) . ? C6 C7 1.391(3) . ? C6 C11 1.393(3) . ? C7 F1 1.339(3) . ? C7 C8 1.372(3) . ? C8 F2 1.341(3) . ? C8 C9 1.373(3) . ? C9 F3 1.334(3) . ? C9 C10 1.379(4) . ? C10 F4 1.332(3) . ? C10 C11 1.374(3) . ? C11 F5 1.340(3) . ? C12 C13 1.391(3) . ? C13 C14 1.411(3) . ? C14 C15 1.372(3) . ? C15 C16 1.465(3) . ? C16 C17 1.501(3) . ? C17 C22 1.385(3) . ? C17 C18 1.388(3) . ? C18 F6 1.341(3) . ? C18 C19 1.374(3) . ? C19 F7 1.336(3) . ? C19 C20 1.373(4) . ? C20 F8 1.333(3) . ? C20 C21 1.377(4) . ? C21 F9 1.337(3) . ? C21 C22 1.374(3) . ? C22 F10 1.343(3) . ? 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 C13 90.41(11) . . ? C1 S2 C4 90.54(10) . . ? C12 S3 C15 91.08(11) . . ? C2 C1 C12 112.15(19) . . ? C2 C1 S2 111.90(16) . . ? C12 C1 S2 135.94(17) . . ? C1 C2 C3 113.43(19) . . ? C1 C2 S1 112.67(16) . . ? C3 C2 S1 133.90(17) . . ? C4 C3 C2 110.77(19) . . ? C3 C4 C5 132.1(2) . . ? C3 C4 S2 113.34(16) . . ? C5 C4 S2 114.49(16) . . ? O1 C5 C4 120.1(2) . . ? O1 C5 C6 119.7(2) . . ? C4 C5 C6 120.16(19) . . ? C7 C6 C11 116.4(2) . . ? C7 C6 C5 124.2(2) . . ? C11 C6 C5 119.2(2) . . ? F1 C7 C8 118.3(2) . . ? F1 C7 C6 119.9(2) . . ? C8 C7 C6 121.7(2) . . ? F2 C8 C7 120.6(2) . . ? F2 C8 C9 119.2(2) . . ? C7 C8 C9 120.2(2) . . ? F3 C9 C8 119.8(2) . . ? F3 C9 C10 120.3(2) . . ? C8 C9 C10 120.0(2) . . ? F4 C10 C11 121.0(2) . . ? F4 C10 C9 119.9(2) . . ? C11 C10 C9 119.1(2) . . ? F5 C11 C10 117.8(2) . . ? F5 C11 C6 119.7(2) . . ? C10 C11 C6 122.5(2) . . ? C13 C12 C1 112.40(19) . . ? C13 C12 S3 111.11(16) . . ? C1 C12 S3 136.46(17) . . ? C12 C13 C14 114.1(2) . . ? C12 C13 S1 112.30(16) . . ? C14 C13 S1 133.64(18) . . ? C15 C14 C13 110.7(2) . . ? C14 C15 C16 132.7(2) . . ? C14 C15 S3 112.99(16) . . ? C16 C15 S3 114.12(16) . . ? O2 C16 C15 120.0(2) . . ? O2 C16 C17 119.6(2) . . ? C15 C16 C17 120.3(2) . . ? C22 C17 C18 116.3(2) . . ? C22 C17 C16 124.8(2) . . ? C18 C17 C16 118.9(2) . . ? F6 C18 C19 117.7(2) . . ? F6 C18 C17 120.0(2) . . ? C19 C18 C17 122.2(2) . . ? F7 C19 C20 119.7(2) . . ? F7 C19 C18 120.6(2) . . ? C20 C19 C18 119.7(2) . . ? F8 C20 C19 120.2(2) . . ? F8 C20 C21 119.9(2) . . ? C19 C20 C21 119.9(2) . . ? F9 C21 C22 120.5(2) . . ? F9 C21 C20 120.0(2) . . ? C22 C21 C20 119.4(2) . . ? F10 C22 C21 117.7(2) . . ? F10 C22 C17 119.9(2) . . ? C21 C22 C17 122.4(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.364 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.063 # Attachment 'FBB_DTT.cif' data_ic13240 _database_code_depnum_ccdc_archive 'CCDC 710106' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H7 F5 O2 S3' _chemical_formula_weight 494.46 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 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 6.2481(3) _cell_length_b 40.288(2) _cell_length_c 7.7740(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.7950(12) _cell_angle_gamma 90.00 _cell_volume 1863.27(16) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.50 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.763 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.467 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7669 _exptl_absorpt_correction_T_max 0.9548 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9650 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -46 _diffrn_reflns_limit_k_max 52 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.01 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4183 _reflns_number_gt 3332 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+1.1641P] 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 4183 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1122 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 0.95667(9) 0.259183(13) 0.08846(9) 0.03622(16) Uani 1 1 d . . . S2 S 0.38417(9) 0.212055(13) 0.13712(10) 0.04084(17) Uani 1 1 d . . . S3 S 0.94678(8) 0.162981(13) 0.08108(8) 0.03228(14) Uani 1 1 d . . . O1 O 1.0630(3) 0.32570(4) 0.1190(3) 0.0579(6) Uani 1 1 d . . . O2 O 1.0179(2) 0.09252(4) 0.0960(2) 0.0377(4) Uani 1 1 d . . . C1 C 0.7730(3) 0.28991(5) 0.1126(3) 0.0330(5) Uani 1 1 d . . . C2 C 0.5777(3) 0.27724(5) 0.1320(3) 0.0340(5) Uani 1 1 d . . . H2 H 0.4593 0.2903 0.1490 0.041 Uiso 1 1 calc R . . C3 C 0.5758(3) 0.24239(5) 0.1235(3) 0.0319(5) Uani 1 1 d . . . C4 C 0.7711(3) 0.22889(5) 0.1011(3) 0.0301(4) Uani 1 1 d . . . C5 C 0.7671(3) 0.19395(5) 0.0982(3) 0.0285(4) Uani 1 1 d . . . C6 C 0.5675(3) 0.18118(5) 0.1146(3) 0.0312(4) Uani 1 1 d . . . C7 C 0.5592(3) 0.14638(5) 0.1155(3) 0.0309(4) Uani 1 1 d . . . H7 H 0.4358 0.1337 0.1266 0.037 Uiso 1 1 calc R . . C8 C 0.7547(3) 0.13311(5) 0.0982(3) 0.0280(4) Uani 1 1 d . . . C9 C 0.8632(4) 0.32340(5) 0.1095(3) 0.0366(5) Uani 1 1 d . . . C10 C 0.7259(3) 0.35393(5) 0.0947(3) 0.0310(4) Uani 1 1 d . . . C11 C 0.8401(4) 0.38358(5) 0.1491(3) 0.0354(5) Uani 1 1 d . . . H11 H 0.9989 0.3835 0.2010 0.042 Uiso 1 1 calc R . . C12 C 0.7243(4) 0.41313(6) 0.1281(3) 0.0397(5) Uani 1 1 d . . . H12 H 0.8031 0.4333 0.1665 0.048 Uiso 1 1 calc R . . C13 C 0.4919(4) 0.41349(6) 0.0506(3) 0.0403(5) Uani 1 1 d . . . H13 H 0.4124 0.4339 0.0345 0.048 Uiso 1 1 calc R . . C14 C 0.3773(4) 0.38419(6) -0.0025(3) 0.0375(5) Uani 1 1 d . . . H14 H 0.2186 0.3845 -0.0549 0.045 Uiso 1 1 calc R . . C15 C 0.4921(3) 0.35439(5) 0.0199(3) 0.0331(5) Uani 1 1 d . . . H15 H 0.4121 0.3342 -0.0155 0.040 Uiso 1 1 calc R . . C16 C 0.8298(3) 0.09900(5) 0.1036(3) 0.0282(4) Uani 1 1 d . . . C17 C 0.6812(3) 0.07127(5) 0.1282(3) 0.0285(4) Uani 1 1 d . . . C18 C 0.7701(3) 0.04760(5) 0.2607(3) 0.0347(5) Uani 1 1 d . . . C19 C 0.6480(4) 0.02117(6) 0.2874(4) 0.0429(6) Uani 1 1 d . . . C20 C 0.4303(4) 0.01693(6) 0.1761(4) 0.0432(6) Uani 1 1 d . . . C21 C 0.3379(3) 0.03918(6) 0.0420(3) 0.0383(5) Uani 1 1 d . . . C22 C 0.4606(3) 0.06633(5) 0.0209(3) 0.0310(4) Uani 1 1 d . . . F1 F 0.9815(2) 0.05095(4) 0.3710(2) 0.0483(4) Uani 1 1 d . . . F2 F 0.7364(3) -0.00074(4) 0.4187(3) 0.0680(5) Uani 1 1 d . . . F3 F 0.3132(3) -0.00950(4) 0.1984(3) 0.0641(5) Uani 1 1 d . . . F4 F 0.1313(2) 0.03391(4) -0.0713(2) 0.0526(4) Uani 1 1 d . . . F5 F 0.3651(2) 0.08740(4) -0.11285(18) 0.0418(3) 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 0.0232(2) 0.0238(3) 0.0657(4) 0.0000(2) 0.0195(2) 0.00042(18) S2 0.0246(3) 0.0236(3) 0.0802(5) 0.0025(3) 0.0248(3) 0.00194(19) S3 0.0234(2) 0.0235(3) 0.0535(3) -0.0005(2) 0.0171(2) 0.00108(18) O1 0.0303(8) 0.0323(9) 0.1193(18) -0.0016(10) 0.0352(10) -0.0021(7) O2 0.0263(7) 0.0348(8) 0.0561(10) 0.0003(7) 0.0187(7) 0.0056(6) C1 0.0242(10) 0.0253(10) 0.0496(13) 0.0002(9) 0.0116(9) 0.0024(8) C2 0.0224(9) 0.0263(10) 0.0551(14) 0.0018(9) 0.0144(9) 0.0021(8) C3 0.0210(9) 0.0262(10) 0.0493(13) 0.0016(9) 0.0116(9) 0.0005(7) C4 0.0217(9) 0.0238(10) 0.0455(12) 0.0002(9) 0.0112(8) 0.0003(7) C5 0.0227(9) 0.0233(10) 0.0406(11) 0.0018(8) 0.0113(8) 0.0022(7) C6 0.0219(9) 0.0261(10) 0.0473(13) 0.0014(9) 0.0132(9) 0.0035(8) C7 0.0257(9) 0.0250(10) 0.0444(12) 0.0015(9) 0.0142(9) -0.0002(8) C8 0.0239(9) 0.0250(10) 0.0363(11) 0.0012(8) 0.0113(8) -0.0014(7) C9 0.0285(10) 0.0275(11) 0.0559(14) -0.0002(10) 0.0157(10) -0.0019(8) C10 0.0304(10) 0.0250(10) 0.0399(12) 0.0001(8) 0.0144(9) -0.0011(8) C11 0.0319(10) 0.0303(11) 0.0431(12) 0.0010(9) 0.0102(9) -0.0025(9) C12 0.0485(13) 0.0256(11) 0.0455(13) -0.0032(9) 0.0150(11) -0.0044(9) C13 0.0470(13) 0.0312(12) 0.0451(13) 0.0043(10) 0.0177(11) 0.0109(10) C14 0.0339(11) 0.0374(12) 0.0424(13) 0.0036(10) 0.0134(9) 0.0055(9) C15 0.0281(10) 0.0297(11) 0.0425(12) -0.0002(9) 0.0125(9) -0.0016(8) C16 0.0256(9) 0.0277(10) 0.0316(10) -0.0019(8) 0.0092(8) 0.0022(8) C17 0.0243(9) 0.0233(10) 0.0387(11) -0.0016(8) 0.0107(8) 0.0029(7) C18 0.0243(9) 0.0298(11) 0.0459(13) 0.0023(9) 0.0048(9) 0.0025(8) C19 0.0384(12) 0.0300(12) 0.0589(15) 0.0100(11) 0.0127(11) 0.0039(9) C20 0.0364(12) 0.0262(11) 0.0705(17) -0.0019(11) 0.0213(12) -0.0045(9) C21 0.0238(10) 0.0348(12) 0.0540(14) -0.0128(10) 0.0085(9) -0.0010(9) C22 0.0268(9) 0.0295(11) 0.0359(11) -0.0026(9) 0.0082(8) 0.0054(8) F1 0.0282(6) 0.0440(8) 0.0612(9) 0.0147(7) -0.0033(6) 0.0008(6) F2 0.0549(10) 0.0468(9) 0.0936(13) 0.0371(9) 0.0100(9) 0.0015(7) F3 0.0485(9) 0.0377(8) 0.1076(14) 0.0051(9) 0.0261(9) -0.0142(7) F4 0.0269(6) 0.0502(9) 0.0725(10) -0.0172(8) 0.0029(6) -0.0074(6) F5 0.0315(6) 0.0487(8) 0.0404(7) 0.0059(6) 0.0038(5) 0.0051(6) _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 1.707(2) . ? S1 C1 1.737(2) . ? S2 C6 1.736(2) . ? S2 C3 1.737(2) . ? S3 C5 1.710(2) . ? S3 C8 1.733(2) . ? O1 C9 1.232(3) . ? O2 C16 1.223(2) . ? C1 C2 1.373(3) . ? C1 C9 1.465(3) . ? C2 C3 1.405(3) . ? C3 C4 1.395(3) . ? C4 C5 1.408(3) . ? C5 C6 1.390(3) . ? C6 C7 1.403(3) . ? C7 C8 1.377(3) . ? C8 C16 1.449(3) . ? C9 C10 1.484(3) . ? C10 C11 1.390(3) . ? C10 C15 1.398(3) . ? C11 C12 1.377(3) . ? C12 C13 1.392(3) . ? C13 C14 1.377(3) . ? C14 C15 1.382(3) . ? C16 C17 1.502(3) . ? C17 C18 1.389(3) . ? C17 C22 1.390(3) . ? C18 F1 1.343(2) . ? C18 C19 1.363(3) . ? C19 F2 1.334(3) . ? C19 C20 1.382(3) . ? C20 F3 1.332(3) . ? C20 C21 1.362(4) . ? C21 F4 1.339(2) . ? C21 C22 1.374(3) . ? C22 F5 1.334(2) . ? 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 91.18(10) . . ? C6 S2 C3 90.55(10) . . ? C5 S3 C8 90.81(9) . . ? C2 C1 C9 134.7(2) . . ? C2 C1 S1 112.68(16) . . ? C9 C1 S1 112.62(15) . . ? C1 C2 C3 111.18(18) . . ? C4 C3 C2 113.59(18) . . ? C4 C3 S2 112.27(16) . . ? C2 C3 S2 134.13(16) . . ? C3 C4 C5 112.34(18) . . ? C3 C4 S1 111.35(16) . . ? C5 C4 S1 136.29(15) . . ? C6 C5 C4 112.36(18) . . ? C6 C5 S3 111.45(16) . . ? C4 C5 S3 136.19(15) . . ? C5 C6 C7 113.95(18) . . ? C5 C6 S2 112.47(16) . . ? C7 C6 S2 133.54(16) . . ? C8 C7 C6 110.60(18) . . ? C7 C8 C16 130.87(19) . . ? C7 C8 S3 113.19(16) . . ? C16 C8 S3 115.81(14) . . ? O1 C9 C1 117.2(2) . . ? O1 C9 C10 119.6(2) . . ? C1 C9 C10 123.27(18) . . ? C11 C10 C15 119.3(2) . . ? C11 C10 C9 117.27(19) . . ? C15 C10 C9 123.33(19) . . ? C12 C11 C10 120.3(2) . . ? C11 C12 C13 120.1(2) . . ? C14 C13 C12 119.9(2) . . ? C13 C14 C15 120.3(2) . . ? C14 C15 C10 120.0(2) . . ? O2 C16 C8 120.58(19) . . ? O2 C16 C17 119.19(18) . . ? C8 C16 C17 120.15(17) . . ? C18 C17 C22 116.44(19) . . ? C18 C17 C16 118.86(17) . . ? C22 C17 C16 124.62(19) . . ? F1 C18 C19 117.9(2) . . ? F1 C18 C17 119.79(19) . . ? C19 C18 C17 122.3(2) . . ? F2 C19 C18 120.9(2) . . ? F2 C19 C20 119.7(2) . . ? C18 C19 C20 119.4(2) . . ? F3 C20 C21 120.3(2) . . ? F3 C20 C19 119.5(2) . . ? C21 C20 C19 120.2(2) . . ? F4 C21 C20 119.8(2) . . ? F4 C21 C22 120.6(2) . . ? C20 C21 C22 119.6(2) . . ? F5 C22 C21 117.82(18) . . ? F5 C22 C17 120.14(19) . . ? C21 C22 C17 122.0(2) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.317 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.061