# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_a _database_code_depnum_ccdc_archive 'CCDC 914092' #TrackingRef '10a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Bis-(pentafluorobenzoyl)-benzo[1,2-b:6,5-b']dithiophene-4,5-dione ; _chemical_name_common ; 2,7-Bis-(pentafluorobenzoyl)-benzo[1,2-b:6,5-b']dithiophene-4,5-dione ; _chemical_melting_point ? _chemical_formula_moiety 'C24 H2 F10 O4 S2' _chemical_formula_sum 'C24 H2 F10 O4 S2' _chemical_formula_weight 608.38 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 P21/n _symmetry_space_group_name_Hall -P2yn 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 6.9519(12) _cell_length_b 7.8710(13) _cell_length_c 38.831(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.118(3) _cell_angle_gamma 90.00 _cell_volume 2123.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1092 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 25.48 _exptl_crystal_description plates _exptl_crystal_colour red _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.903 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.374 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6427 _exptl_absorpt_correction_T_max 0.7470 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22506 _diffrn_reflns_av_R_equivalents 0.0624 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -50 _diffrn_reflns_limit_l_max 50 _diffrn_reflns_theta_min 1.05 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4861 _reflns_number_gt 3564 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0415P)^2^+1.7846P] 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 4861 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.0909 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.03841(9) 0.78211(8) 0.282942(16) 0.01909(15) Uani 1 1 d . . . S2 S 0.06421(10) 0.80303(8) 0.194826(16) 0.01979(15) Uani 1 1 d . . . F1 F 0.3814(2) 0.9120(2) 0.07641(4) 0.0272(4) Uani 1 1 d . . . F2 F 0.3155(3) 1.0811(2) 0.01712(4) 0.0387(4) Uani 1 1 d . . . F3 F -0.0317(3) 1.2273(2) 0.00335(4) 0.0425(5) Uani 1 1 d . . . F4 F -0.3197(3) 1.1910(2) 0.04796(5) 0.0410(5) Uani 1 1 d . . . F5 F -0.2581(2) 1.0192(2) 0.10698(4) 0.0340(4) Uani 1 1 d . . . F6 F -0.3077(2) 0.9812(2) 0.37199(4) 0.0332(4) Uani 1 1 d . . . F7 F -0.3422(3) 1.1426(2) 0.43276(5) 0.0388(4) Uani 1 1 d . . . F8 F -0.0381(3) 1.1563(2) 0.47854(4) 0.0377(4) Uani 1 1 d . . . F9 F 0.3010(2) 1.0105(2) 0.46326(4) 0.0355(4) Uani 1 1 d . . . F10 F 0.3394(2) 0.8564(2) 0.40213(4) 0.0249(4) Uani 1 1 d . . . O1 O -0.0838(3) 1.3991(2) 0.27779(5) 0.0267(4) Uani 1 1 d . . . O2 O -0.0538(3) 1.4172(2) 0.20784(5) 0.0250(4) Uani 1 1 d . . . O3 O 0.1766(3) 0.7223(2) 0.12491(5) 0.0273(4) Uani 1 1 d . . . O4 O 0.0832(3) 0.6621(2) 0.35476(5) 0.0244(4) Uani 1 1 d . . . C1 C 0.0145(4) 0.9006(3) 0.32037(6) 0.0188(5) Uani 1 1 d . . . C2 C -0.0164(4) 1.0685(3) 0.31357(7) 0.0195(5) Uani 1 1 d . . . H2 H -0.0325 1.1502 0.3305 0.023 Uiso 1 1 calc R . . C3 C -0.0213(4) 1.1044(3) 0.27815(7) 0.0190(5) Uani 1 1 d . . . C4 C 0.0090(3) 0.9614(3) 0.25843(7) 0.0184(5) Uani 1 1 d . . . C5 C 0.0163(4) 0.9692(3) 0.22134(7) 0.0179(5) Uani 1 1 d . . . C6 C -0.0097(4) 1.1200(3) 0.20355(7) 0.0183(5) Uani 1 1 d . . . C7 C -0.0410(4) 1.2806(3) 0.22185(6) 0.0189(5) Uani 1 1 d . . . C8 C -0.0518(4) 1.2708(3) 0.26197(7) 0.0194(5) Uani 1 1 d . . . C9 C 0.0078(4) 1.0995(3) 0.16781(7) 0.0197(5) Uani 1 1 d . . . H9 H -0.0074 1.1871 0.1519 0.024 Uiso 1 1 calc R . . C10 C 0.0499(4) 0.9354(3) 0.15924(6) 0.0185(5) Uani 1 1 d . . . C11 C 0.1016(4) 0.8612(3) 0.12627(7) 0.0209(6) Uani 1 1 d . . . C12 C 0.0654(4) 0.9631(3) 0.09406(7) 0.0192(5) Uani 1 1 d . . . C13 C 0.2071(4) 0.9806(3) 0.07014(7) 0.0217(6) Uani 1 1 d . . . C14 C 0.1755(4) 1.0683(4) 0.03995(7) 0.0265(6) Uani 1 1 d . . . C15 C -0.0002(5) 1.1417(4) 0.03259(7) 0.0291(7) Uani 1 1 d . . . C16 C -0.1468(4) 1.1240(4) 0.05541(7) 0.0286(7) Uani 1 1 d . . . C17 C -0.1120(4) 1.0365(4) 0.08568(7) 0.0240(6) Uani 1 1 d . . . C18 C 0.0393(4) 0.8110(3) 0.35302(6) 0.0192(5) Uani 1 1 d . . . C19 C 0.0167(4) 0.9111(3) 0.38585(7) 0.0203(5) Uani 1 1 d . . . C20 C -0.1553(4) 0.9892(4) 0.39411(7) 0.0242(6) Uani 1 1 d . . . C21 C -0.1746(4) 1.0708(4) 0.42518(7) 0.0267(6) Uani 1 1 d . . . C22 C -0.0206(4) 1.0764(3) 0.44866(7) 0.0268(6) Uani 1 1 d . . . C23 C 0.1517(4) 1.0018(3) 0.44098(7) 0.0237(6) Uani 1 1 d . . . C24 C 0.1682(4) 0.9220(3) 0.40970(7) 0.0210(6) 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 0.0230(3) 0.0153(3) 0.0191(3) 0.0021(2) 0.0028(2) 0.0018(3) S2 0.0245(3) 0.0155(3) 0.0197(3) 0.0005(2) 0.0043(2) 0.0013(3) F1 0.0226(8) 0.0321(9) 0.0274(9) 0.0001(7) 0.0060(6) 0.0027(7) F2 0.0497(11) 0.0443(11) 0.0228(9) 0.0054(8) 0.0103(8) -0.0100(9) F3 0.0723(14) 0.0316(10) 0.0224(9) 0.0050(7) -0.0140(9) -0.0008(10) F4 0.0431(11) 0.0384(11) 0.0400(10) -0.0086(8) -0.0184(8) 0.0167(9) F5 0.0204(8) 0.0507(11) 0.0310(9) -0.0064(8) 0.0030(7) 0.0048(8) F6 0.0210(8) 0.0481(11) 0.0306(9) -0.0024(8) 0.0022(7) 0.0061(8) F7 0.0363(10) 0.0430(11) 0.0379(10) -0.0031(8) 0.0145(8) 0.0149(9) F8 0.0565(12) 0.0333(10) 0.0239(9) -0.0098(7) 0.0109(8) 0.0025(9) F9 0.0370(10) 0.0402(11) 0.0287(9) -0.0065(8) -0.0069(8) -0.0029(8) F10 0.0206(8) 0.0273(9) 0.0267(8) 0.0014(7) 0.0022(6) 0.0039(7) O1 0.0331(11) 0.0181(10) 0.0285(10) -0.0033(8) -0.0027(8) 0.0024(8) O2 0.0317(11) 0.0164(10) 0.0272(10) 0.0044(8) 0.0029(8) 0.0015(8) O3 0.0365(11) 0.0219(10) 0.0238(10) 0.0003(8) 0.0065(8) 0.0065(9) O4 0.0264(10) 0.0223(10) 0.0247(10) 0.0030(8) 0.0047(8) 0.0037(8) C1 0.0167(12) 0.0210(14) 0.0189(13) -0.0003(10) 0.0025(10) -0.0001(11) C2 0.0191(13) 0.0184(13) 0.0212(13) -0.0019(10) 0.0030(10) -0.0015(11) C3 0.0163(12) 0.0181(13) 0.0226(13) 0.0012(10) 0.0004(10) -0.0011(10) C4 0.0149(12) 0.0180(13) 0.0226(13) 0.0004(10) 0.0034(10) -0.0012(10) C5 0.0160(12) 0.0155(13) 0.0222(13) -0.0006(10) 0.0008(10) -0.0018(10) C6 0.0162(12) 0.0167(13) 0.0220(13) 0.0022(10) -0.0001(10) -0.0015(10) C7 0.0155(12) 0.0187(13) 0.0226(13) 0.0012(11) 0.0003(10) -0.0016(11) C8 0.0180(12) 0.0167(13) 0.0233(13) -0.0001(10) -0.0003(10) -0.0003(11) C9 0.0197(13) 0.0184(13) 0.0212(13) 0.0062(10) 0.0023(10) -0.0004(11) C10 0.0180(12) 0.0188(13) 0.0190(12) 0.0022(10) 0.0050(10) -0.0013(10) C11 0.0218(13) 0.0207(14) 0.0202(13) 0.0010(10) 0.0028(10) -0.0019(11) C12 0.0205(13) 0.0176(13) 0.0198(13) -0.0037(10) 0.0022(10) 0.0005(11) C13 0.0239(14) 0.0198(14) 0.0216(13) -0.0032(11) 0.0020(11) 0.0003(11) C14 0.0382(16) 0.0228(15) 0.0188(13) -0.0019(11) 0.0044(12) -0.0051(13) C15 0.0465(18) 0.0196(14) 0.0204(14) 0.0001(11) -0.0091(13) -0.0005(13) C16 0.0317(16) 0.0239(15) 0.0294(15) -0.0082(12) -0.0101(12) 0.0070(13) C17 0.0243(14) 0.0250(15) 0.0228(14) -0.0084(11) 0.0010(11) 0.0026(12) C18 0.0168(12) 0.0214(14) 0.0195(13) 0.0024(10) 0.0032(10) -0.0002(11) C19 0.0228(13) 0.0194(13) 0.0189(13) 0.0039(10) 0.0039(10) -0.0004(11) C20 0.0224(14) 0.0256(15) 0.0249(14) 0.0052(11) 0.0045(11) 0.0013(12) C21 0.0260(15) 0.0237(15) 0.0312(15) 0.0030(12) 0.0109(12) 0.0045(12) C22 0.0426(17) 0.0188(14) 0.0197(13) -0.0009(11) 0.0088(12) -0.0015(13) C23 0.0290(15) 0.0195(14) 0.0225(13) 0.0029(11) 0.0006(11) -0.0024(12) C24 0.0216(13) 0.0170(13) 0.0246(13) 0.0050(11) 0.0048(11) -0.0008(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C4 1.711(3) . ? S1 C1 1.740(3) . ? S2 C5 1.705(3) . ? S2 C10 1.731(3) . ? F1 C13 1.341(3) . ? F2 C14 1.345(3) . ? F3 C15 1.331(3) . ? F4 C16 1.335(3) . ? F5 C17 1.340(3) . ? F6 C20 1.341(3) . ? F7 C21 1.338(3) . ? F8 C22 1.330(3) . ? F9 C23 1.328(3) . ? F10 C24 1.340(3) . ? O1 C8 1.207(3) . ? O2 C7 1.207(3) . ? O3 C11 1.213(3) . ? O4 C18 1.213(3) . ? C1 C2 1.363(4) . ? C1 C18 1.455(3) . ? C2 C3 1.403(4) . ? C2 H2 0.9300 . ? C3 C4 1.382(4) . ? C3 C8 1.465(4) . ? C4 C5 1.444(4) . ? C5 C6 1.381(4) . ? C6 C9 1.407(4) . ? C6 C7 1.471(4) . ? C7 C8 1.564(4) . ? C9 C10 1.368(4) . ? C9 H9 0.9300 . ? C10 C11 1.464(4) . ? C11 C12 1.500(4) . ? C12 C13 1.386(4) . ? C12 C17 1.389(4) . ? C13 C14 1.372(4) . ? C14 C15 1.371(4) . ? C15 C16 1.382(4) . ? C16 C17 1.376(4) . ? C18 C19 1.512(4) . ? C19 C24 1.379(4) . ? C19 C20 1.392(4) . ? C20 C21 1.378(4) . ? C21 C22 1.381(4) . ? C22 C23 1.376(4) . ? C23 C24 1.376(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 C4 S1 C1 90.54(13) . . ? C5 S2 C10 90.76(13) . . ? C2 C1 C18 130.6(2) . . ? C2 C1 S1 112.15(19) . . ? C18 C1 S1 117.1(2) . . ? C1 C2 C3 112.5(2) . . ? C1 C2 H2 123.7 . . ? C3 C2 H2 123.7 . . ? C4 C3 C2 112.4(2) . . ? C4 C3 C8 120.9(2) . . ? C2 C3 C8 126.8(2) . . ? C3 C4 C5 122.0(2) . . ? C3 C4 S1 112.41(19) . . ? C5 C4 S1 125.6(2) . . ? C6 C5 C4 121.8(2) . . ? C6 C5 S2 112.4(2) . . ? C4 C5 S2 125.8(2) . . ? C5 C6 C9 112.4(2) . . ? C5 C6 C7 121.0(2) . . ? C9 C6 C7 126.5(2) . . ? O2 C7 C6 123.9(2) . . ? O2 C7 C8 119.2(2) . . ? C6 C7 C8 116.9(2) . . ? O1 C8 C3 123.8(2) . . ? O1 C8 C7 118.8(2) . . ? C3 C8 C7 117.4(2) . . ? C10 C9 C6 112.0(2) . . ? C10 C9 H9 124.0 . . ? C6 C9 H9 124.0 . . ? C9 C10 C11 130.6(2) . . ? C9 C10 S2 112.4(2) . . ? C11 C10 S2 116.67(19) . . ? O3 C11 C10 121.2(2) . . ? O3 C11 C12 120.3(2) . . ? C10 C11 C12 118.5(2) . . ? C13 C12 C17 116.7(2) . . ? C13 C12 C11 120.7(2) . . ? C17 C12 C11 122.6(2) . . ? F1 C13 C14 118.3(2) . . ? F1 C13 C12 119.9(2) . . ? C14 C13 C12 121.8(3) . . ? F2 C14 C15 119.5(3) . . ? F2 C14 C13 120.2(3) . . ? C15 C14 C13 120.2(3) . . ? F3 C15 C14 120.5(3) . . ? F3 C15 C16 119.7(3) . . ? C14 C15 C16 119.7(3) . . ? F4 C16 C17 120.8(3) . . ? F4 C16 C15 120.0(3) . . ? C17 C16 C15 119.2(3) . . ? F5 C17 C16 117.7(2) . . ? F5 C17 C12 120.0(2) . . ? C16 C17 C12 122.3(3) . . ? O4 C18 C1 122.6(2) . . ? O4 C18 C19 119.4(2) . . ? C1 C18 C19 118.0(2) . . ? C24 C19 C20 117.3(2) . . ? C24 C19 C18 119.9(2) . . ? C20 C19 C18 122.8(2) . . ? F6 C20 C21 118.9(2) . . ? F6 C20 C19 119.8(2) . . ? C21 C20 C19 121.3(3) . . ? F7 C21 C20 120.2(3) . . ? F7 C21 C22 120.1(3) . . ? C20 C21 C22 119.6(3) . . ? F8 C22 C23 120.0(3) . . ? F8 C22 C21 119.8(3) . . ? C23 C22 C21 120.2(3) . . ? F9 C23 C24 120.7(3) . . ? F9 C23 C22 120.1(3) . . ? C24 C23 C22 119.2(3) . . ? F10 C24 C23 118.2(2) . . ? F10 C24 C19 119.4(2) . . ? C23 C24 C19 122.3(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.392 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.074 data_14 _database_code_depnum_ccdc_archive 'CCDC 914093' #TrackingRef '10c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Bis-(4-trifluoromethylbenzoyl)-benzo[1,2-b:6,5-b']dithiophene-4,5-dione ; _chemical_name_common ; 2,7-Bis-(4-trifluoromethylbenzoyl)-benzo[1,2-b:6,5-b']dithiophene-4,5-dione ; _chemical_melting_point ? _chemical_formula_moiety 'C26 H10 F6 O4 S2' _chemical_formula_sum 'C26 H10 F6 O4 S2' _chemical_formula_weight 564.46 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)/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 8.5420(9) _cell_length_b 5.9376(6) _cell_length_c 44.370(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.560(2) _cell_angle_gamma 90.00 _cell_volume 2246.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.322 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.919 _exptl_absorpt_correction_T_max 0.950 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25278 _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -52 _diffrn_reflns_limit_l_max 52 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3960 _reflns_number_gt 3099 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0297P)^2^+3.2440P] 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 3960 _refine_ls_number_parameters 385 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.1130 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.119 _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 0.15434(11) 0.22917(15) 0.016462(19) 0.0427(2) Uani 1 1 d . . . S2 S 0.21095(11) 0.06538(15) 0.091041(19) 0.0414(2) Uani 1 1 d . . . O1 O 0.5513(3) 0.7304(4) 0.10349(6) 0.0553(7) Uani 1 1 d . . . O2 O 0.5168(3) 0.8542(4) 0.04359(6) 0.0578(7) Uani 1 1 d . . . O3 O 0.2386(3) -0.2193(4) 0.14555(6) 0.0605(7) Uani 1 1 d . . . O4 O 0.0303(3) 0.2185(5) -0.04154(6) 0.0651(8) Uani 1 1 d . . . F1 F 0.4276(8) 0.1805(18) 0.29173(15) 0.089(3) Uani 0.643(11) 1 d PD A 1 F2 F 0.6636(8) 0.0952(15) 0.27973(15) 0.089(2) Uani 0.643(11) 1 d PD A 1 F3 F 0.5803(13) 0.4273(11) 0.27211(13) 0.091(2) Uani 0.643(11) 1 d PD A 1 F1' F 0.562(4) 0.019(4) 0.2855(5) 0.089(3) Uani 0.127(6) 1 d PD A 2 F2' F 0.637(4) 0.335(7) 0.2683(7) 0.089(2) Uani 0.127(6) 1 d PD A 2 F3' F 0.413(3) 0.320(6) 0.2843(7) 0.091(2) Uani 0.127(6) 1 d PD A 2 F1'' F 0.467(4) 0.078(4) 0.2909(5) 0.089(3) Uani 0.230(9) 1 d PD A 3 F2'' F 0.669(2) 0.198(5) 0.2741(5) 0.089(2) Uani 0.230(9) 1 d PD A 3 F3'' F 0.483(3) 0.435(3) 0.2773(4) 0.091(2) Uani 0.230(9) 1 d PD A 3 F4 F 0.112(3) 1.060(4) -0.1507(5) 0.078(2) Uani 0.135(5) 1 d PD B 1 F5 F 0.092(4) 0.754(5) -0.1759(5) 0.0700(16) Uani 0.135(5) 1 d PD B 1 F6 F 0.307(3) 0.862(5) -0.1603(6) 0.093(3) Uani 0.135(5) 1 d PD B 1 F4' F 0.0429(6) 0.8439(16) -0.16958(16) 0.078(2) Uani 0.647(10) 1 d PD B 2 F5' F 0.2786(8) 0.7310(10) -0.17049(11) 0.0700(16) Uani 0.647(10) 1 d PD B 2 F6' F 0.2373(12) 1.0534(10) -0.1518(2) 0.093(3) Uani 0.647(10) 1 d PD B 2 F4'' F 0.041(2) 0.971(4) -0.1596(4) 0.078(2) Uani 0.218(8) 1 d PD B 3 F5'' F 0.200(3) 0.721(3) -0.1743(3) 0.0700(16) Uani 0.218(8) 1 d PD B 3 F6'' F 0.290(4) 0.994(5) -0.1506(8) 0.093(3) Uani 0.218(8) 1 d PD B 3 C1 C 0.2003(4) 0.4284(6) -0.01058(7) 0.0399(8) Uani 1 1 d . . . C2 C 0.3011(4) 0.5874(6) 0.00157(7) 0.0415(8) Uani 1 1 d . . . H2A H 0.3396 0.7097 -0.0096 0.050 Uiso 1 1 calc R . . C3 C 0.3423(4) 0.5511(6) 0.03257(7) 0.0393(8) Uani 1 1 d . . . C4 C 0.2694(4) 0.3633(6) 0.04351(7) 0.0370(8) Uani 1 1 d . . . C5 C 0.2911(4) 0.2964(5) 0.07488(7) 0.0363(7) Uani 1 1 d . . . C6 C 0.3841(4) 0.4183(5) 0.09531(7) 0.0370(8) Uani 1 1 d . . . C7 C 0.4683(4) 0.6199(6) 0.08619(8) 0.0409(8) Uani 1 1 d . . . C8 C 0.4466(4) 0.6912(6) 0.05241(8) 0.0409(8) Uani 1 1 d . . . C9 C 0.3915(4) 0.3231(6) 0.12454(7) 0.0396(8) Uani 1 1 d . . . H9A H 0.4507 0.3852 0.1414 0.047 Uiso 1 1 calc R . . C10 C 0.3038(4) 0.1313(6) 0.12579(7) 0.0385(8) Uani 1 1 d . . . C11 C 0.2920(4) -0.0316(6) 0.15058(8) 0.0431(8) Uani 1 1 d . . . C12 C 0.3529(4) 0.0349(6) 0.18157(7) 0.0400(8) Uani 1 1 d . . . C13 C 0.4428(5) -0.1160(6) 0.19869(9) 0.0531(10) Uani 1 1 d . . . H13A H 0.4652 -0.2600 0.1907 0.064 Uiso 1 1 calc R . . C14 C 0.5006(5) -0.0592(7) 0.22749(9) 0.0561(10) Uani 1 1 d . . . H14A H 0.5642 -0.1627 0.2391 0.067 Uiso 1 1 calc R . . C15 C 0.4655(4) 0.1486(7) 0.23937(8) 0.0479(9) Uani 1 1 d . A . C16 C 0.3724(4) 0.2991(6) 0.22275(8) 0.0502(9) Uani 1 1 d . . . H16A H 0.3465 0.4403 0.2312 0.060 Uiso 1 1 calc R . . C17 C 0.3170(4) 0.2443(6) 0.19385(8) 0.0472(9) Uani 1 1 d . . . H17A H 0.2543 0.3488 0.1822 0.057 Uiso 1 1 calc R . . C18 C 0.1190(4) 0.3809(6) -0.04028(8) 0.0417(8) Uani 1 1 d . . . C19 C 0.1377(4) 0.5154(6) -0.06830(7) 0.0383(8) Uani 1 1 d . . . C20 C 0.2143(4) 0.7201(6) -0.06962(8) 0.0461(9) Uani 1 1 d . . . H20A H 0.2584 0.7867 -0.0516 0.055 Uiso 1 1 calc R . . C21 C 0.2276(4) 0.8285(6) -0.09680(8) 0.0491(9) Uani 1 1 d . . . H21A H 0.2809 0.9687 -0.0974 0.059 Uiso 1 1 calc R . . C22 C 0.1635(4) 0.7334(6) -0.12298(7) 0.0418(8) Uani 1 1 d . B . C23 C 0.0849(5) 0.5317(6) -0.12218(8) 0.0505(10) Uani 1 1 d . . . H23A H 0.0393 0.4674 -0.1403 0.061 Uiso 1 1 calc R . . C24 C 0.0729(4) 0.4239(6) -0.09505(8) 0.0504(10) Uani 1 1 d . . . H24A H 0.0192 0.2840 -0.0946 0.060 Uiso 1 1 calc R . . C25 C 0.1754(5) 0.8471(7) -0.15263(9) 0.0528(10) Uani 1 1 d . . . C26 C 0.5268(6) 0.2122(9) 0.27048(10) 0.0700(13) 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 0.0517(5) 0.0368(5) 0.0392(5) 0.0016(4) -0.0011(4) -0.0141(4) S2 0.0492(5) 0.0353(5) 0.0395(5) 0.0007(4) -0.0006(4) -0.0131(4) O1 0.0593(16) 0.0486(16) 0.0563(16) 0.0016(13) -0.0091(13) -0.0247(14) O2 0.0707(18) 0.0479(16) 0.0548(16) 0.0045(13) 0.0042(13) -0.0281(14) O3 0.089(2) 0.0383(15) 0.0536(16) -0.0001(12) 0.0012(14) -0.0209(15) O4 0.091(2) 0.0548(17) 0.0485(15) 0.0053(13) -0.0047(14) -0.0409(16) F1 0.098(5) 0.130(8) 0.0409(18) -0.010(4) 0.021(3) -0.028(5) F2 0.088(3) 0.107(6) 0.067(3) 0.017(4) -0.033(2) 0.001(4) F3 0.120(7) 0.080(3) 0.069(3) -0.016(2) -0.019(4) -0.034(4) F1' 0.098(5) 0.130(8) 0.0409(18) -0.010(4) 0.021(3) -0.028(5) F2' 0.088(3) 0.107(6) 0.067(3) 0.017(4) -0.033(2) 0.001(4) F3' 0.120(7) 0.080(3) 0.069(3) -0.016(2) -0.019(4) -0.034(4) F1'' 0.098(5) 0.130(8) 0.0409(18) -0.010(4) 0.021(3) -0.028(5) F2'' 0.088(3) 0.107(6) 0.067(3) 0.017(4) -0.033(2) 0.001(4) F3'' 0.120(7) 0.080(3) 0.069(3) -0.016(2) -0.019(4) -0.034(4) F4 0.063(2) 0.106(6) 0.063(4) 0.033(3) -0.011(2) -0.003(3) F5 0.063(4) 0.100(3) 0.048(2) 0.001(2) 0.015(3) -0.003(4) F6 0.168(9) 0.052(4) 0.057(2) 0.022(3) -0.006(4) -0.047(5) F4' 0.063(2) 0.106(6) 0.063(4) 0.033(3) -0.011(2) -0.003(3) F5' 0.063(4) 0.100(3) 0.048(2) 0.001(2) 0.015(3) -0.003(4) F6' 0.168(9) 0.052(4) 0.057(2) 0.022(3) -0.006(4) -0.047(5) F4'' 0.063(2) 0.106(6) 0.063(4) 0.033(3) -0.011(2) -0.003(3) F5'' 0.063(4) 0.100(3) 0.048(2) 0.001(2) 0.015(3) -0.003(4) F6'' 0.168(9) 0.052(4) 0.057(2) 0.022(3) -0.006(4) -0.047(5) C1 0.0432(19) 0.0371(19) 0.0397(19) 0.0041(15) 0.0048(15) -0.0059(16) C2 0.048(2) 0.0363(19) 0.0402(19) 0.0026(16) 0.0057(16) -0.0071(16) C3 0.0398(18) 0.0363(19) 0.0424(19) -0.0017(15) 0.0066(15) -0.0071(15) C4 0.0389(18) 0.0334(18) 0.0388(18) -0.0010(15) 0.0019(15) -0.0038(15) C5 0.0360(17) 0.0324(18) 0.0406(18) 0.0006(15) 0.0028(14) -0.0042(15) C6 0.0388(18) 0.0314(18) 0.0409(19) 0.0010(15) 0.0035(15) -0.0046(15) C7 0.0378(18) 0.0364(19) 0.048(2) -0.0023(16) 0.0007(16) -0.0080(16) C8 0.0436(19) 0.0359(19) 0.044(2) 0.0024(16) 0.0066(16) -0.0078(16) C9 0.0426(19) 0.0353(19) 0.0400(19) -0.0024(15) -0.0037(15) -0.0034(16) C10 0.0425(19) 0.0357(19) 0.0370(18) -0.0001(15) -0.0010(15) -0.0065(15) C11 0.050(2) 0.035(2) 0.044(2) -0.0007(16) 0.0044(16) -0.0057(17) C12 0.045(2) 0.0366(19) 0.0390(19) 0.0031(15) 0.0058(15) -0.0099(16) C13 0.070(3) 0.039(2) 0.050(2) 0.0046(18) 0.003(2) 0.0031(19) C14 0.066(3) 0.054(2) 0.048(2) 0.0116(19) -0.0034(19) 0.003(2) C15 0.054(2) 0.053(2) 0.0362(19) 0.0033(17) 0.0036(17) -0.0098(19) C16 0.062(2) 0.041(2) 0.048(2) -0.0088(17) 0.0045(18) -0.0043(19) C17 0.054(2) 0.039(2) 0.048(2) 0.0006(17) 0.0023(17) 0.0051(18) C18 0.046(2) 0.0365(19) 0.042(2) -0.0014(16) 0.0021(16) -0.0107(16) C19 0.0425(19) 0.0364(19) 0.0363(18) -0.0008(15) 0.0046(15) -0.0083(15) C20 0.058(2) 0.038(2) 0.0400(19) -0.0027(16) -0.0071(17) -0.0166(18) C21 0.060(2) 0.039(2) 0.048(2) 0.0047(17) 0.0002(18) -0.0195(18) C22 0.0443(19) 0.042(2) 0.0390(19) 0.0041(16) 0.0042(15) -0.0067(17) C23 0.067(2) 0.045(2) 0.039(2) -0.0041(17) -0.0054(18) -0.0164(19) C24 0.065(2) 0.040(2) 0.045(2) 0.0005(17) -0.0043(18) -0.0234(19) C25 0.052(2) 0.057(3) 0.050(2) 0.008(2) 0.0021(19) -0.013(2) C26 0.076(3) 0.078(4) 0.054(3) 0.005(2) -0.007(2) -0.018(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 C4 1.701(3) . ? S1 C1 1.747(3) . ? S2 C5 1.710(3) . ? S2 C10 1.734(3) . ? O1 C7 1.206(4) . ? O2 C8 1.216(4) . ? O3 C11 1.220(4) . ? O4 C18 1.226(4) . ? F1 C26 1.320(8) . ? F2 C26 1.399(8) . ? F3 C26 1.357(7) . ? F1' C26 1.35(2) . ? F2' C26 1.20(3) . ? F3' C26 1.35(3) . ? F1'' C26 1.33(2) . ? F2'' C26 1.22(2) . ? F3'' C26 1.413(18) . ? F4 C25 1.38(2) . ? F5 C25 1.34(2) . ? F6 C25 1.20(2) . ? F4' C25 1.319(6) . ? F5' C25 1.403(7) . ? F6' C25 1.333(8) . ? F4'' C25 1.379(17) . ? F5'' C25 1.249(16) . ? F6'' C25 1.31(3) . ? C1 C2 1.367(5) . ? C1 C18 1.478(5) . ? C2 C3 1.415(5) . ? C2 H2A 0.9500 . ? C3 C4 1.380(5) . ? C3 C8 1.471(5) . ? C4 C5 1.449(4) . ? C5 C6 1.374(4) . ? C6 C9 1.413(4) . ? C6 C7 1.466(5) . ? C7 C8 1.558(5) . ? C9 C10 1.366(5) . ? C9 H9A 0.9500 . ? C10 C11 1.473(5) . ? C11 C12 1.493(5) . ? C12 C13 1.377(5) . ? C12 C17 1.399(5) . ? C13 C14 1.383(5) . ? C13 H13A 0.9500 . ? C14 C15 1.382(5) . ? C14 H14A 0.9500 . ? C15 C16 1.379(5) . ? C15 C26 1.494(5) . ? C16 C17 1.378(5) . ? C16 H16A 0.9500 . ? C17 H17A 0.9500 . ? C18 C19 1.495(5) . ? C19 C20 1.384(5) . ? C19 C24 1.389(5) . ? C20 C21 1.378(5) . ? C20 H20A 0.9500 . ? C21 C22 1.374(5) . ? C21 H21A 0.9500 . ? C22 C23 1.374(5) . ? C22 C25 1.488(5) . ? C23 C24 1.373(5) . ? C23 H23A 0.9500 . ? C24 H24A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 S1 C1 91.31(16) . . ? C5 S2 C10 91.08(16) . . ? C2 C1 C18 137.2(3) . . ? C2 C1 S1 111.1(3) . . ? C18 C1 S1 111.7(2) . . ? C1 C2 C3 113.0(3) . . ? C1 C2 H2A 123.5 . . ? C3 C2 H2A 123.5 . . ? C4 C3 C2 112.0(3) . . ? C4 C3 C8 121.1(3) . . ? C2 C3 C8 126.9(3) . . ? C3 C4 C5 121.8(3) . . ? C3 C4 S1 112.6(3) . . ? C5 C4 S1 125.7(2) . . ? C6 C5 C4 121.6(3) . . ? C6 C5 S2 112.1(2) . . ? C4 C5 S2 126.3(2) . . ? C5 C6 C9 112.7(3) . . ? C5 C6 C7 121.5(3) . . ? C9 C6 C7 125.8(3) . . ? O1 C7 C6 123.2(3) . . ? O1 C7 C8 119.6(3) . . ? C6 C7 C8 117.1(3) . . ? O2 C8 C3 123.4(3) . . ? O2 C8 C7 119.6(3) . . ? C3 C8 C7 117.0(3) . . ? C10 C9 C6 112.2(3) . . ? C10 C9 H9A 123.9 . . ? C6 C9 H9A 123.9 . . ? C9 C10 C11 129.8(3) . . ? C9 C10 S2 112.0(3) . . ? C11 C10 S2 117.8(2) . . ? O3 C11 C10 120.4(3) . . ? O3 C11 C12 121.0(3) . . ? C10 C11 C12 118.6(3) . . ? C13 C12 C17 119.5(3) . . ? C13 C12 C11 119.1(3) . . ? C17 C12 C11 121.4(3) . . ? C12 C13 C14 120.4(4) . . ? C12 C13 H13A 119.8 . . ? C14 C13 H13A 119.8 . . ? C15 C14 C13 119.8(4) . . ? C15 C14 H14A 120.1 . . ? C13 C14 H14A 120.1 . . ? C16 C15 C14 120.4(3) . . ? C16 C15 C26 119.2(4) . . ? C14 C15 C26 120.4(4) . . ? C17 C16 C15 119.8(4) . . ? C17 C16 H16A 120.1 . . ? C15 C16 H16A 120.1 . . ? C16 C17 C12 120.1(3) . . ? C16 C17 H17A 120.0 . . ? C12 C17 H17A 120.0 . . ? O4 C18 C1 116.5(3) . . ? O4 C18 C19 118.7(3) . . ? C1 C18 C19 124.8(3) . . ? C20 C19 C24 118.2(3) . . ? C20 C19 C18 125.4(3) . . ? C24 C19 C18 116.4(3) . . ? C21 C20 C19 120.8(3) . . ? C21 C20 H20A 119.6 . . ? C19 C20 H20A 119.6 . . ? C22 C21 C20 119.9(3) . . ? C22 C21 H21A 120.1 . . ? C20 C21 H21A 120.1 . . ? C23 C22 C21 120.4(3) . . ? C23 C22 C25 118.6(3) . . ? C21 C22 C25 121.0(3) . . ? C24 C23 C22 119.5(3) . . ? C24 C23 H23A 120.3 . . ? C22 C23 H23A 120.3 . . ? C23 C24 C19 121.3(3) . . ? C23 C24 H24A 119.3 . . ? C19 C24 H24A 119.3 . . ? F6 C25 F5'' 67.9(15) . . ? F6 C25 F6'' 42.0(16) . . ? F5'' C25 F6'' 107.0(17) . . ? F6 C25 F4' 128.8(12) . . ? F5'' C25 F4' 74.3(9) . . ? F6'' C25 F4' 131.3(12) . . ? F6 C25 F6' 64.0(15) . . ? F5'' C25 F6' 119.4(10) . . ? F6'' C25 F6' 25.1(15) . . ? F4' C25 F6' 110.7(5) . . ? F6 C25 F5 106.1(15) . . ? F5'' C25 F5 42.4(11) . . ? F6'' C25 F5 133.5(18) . . ? F4' C25 F5 32.5(12) . . ? F6' C25 F5 126.4(12) . . ? F6 C25 F4 109.3(14) . . ? F5'' C25 F4 133.1(12) . . ? F6'' C25 F4 71.7(15) . . ? F4' C25 F4 73.8(11) . . ? F6' C25 F4 46.8(13) . . ? F5 C25 F4 103.5(14) . . ? F6 C25 F4'' 132.6(13) . . ? F5'' C25 F4'' 108.9(11) . . ? F6'' C25 F4'' 105.5(13) . . ? F4' C25 F4'' 37.9(9) . . ? F6' C25 F4'' 80.7(11) . . ? F5 C25 F4'' 69.8(14) . . ? F4 C25 F4'' 36.9(11) . . ? F6 C25 F5' 40.8(15) . . ? F5'' C25 F5' 29.4(9) . . ? F6'' C25 F5' 82.6(17) . . ? F4' C25 F5' 102.6(5) . . ? F6' C25 F5' 101.9(6) . . ? F5 C25 F5' 71.6(13) . . ? F4 C25 F5' 138.5(10) . . ? F4'' C25 F5' 132.7(9) . . ? F6 C25 C22 113.7(10) . . ? F5'' C25 C22 115.6(9) . . ? F6'' C25 C22 109.5(14) . . ? F4' C25 C22 113.2(4) . . ? F6' C25 C22 116.1(5) . . ? F5 C25 C22 115.6(11) . . ? F4 C25 C22 108.1(9) . . ? F4'' C25 C22 109.8(7) . . ? F5' C25 C22 110.9(4) . . ? F2' C26 F2'' 43.4(16) . . ? F2' C26 F1 133.3(17) . . ? F2'' C26 F1 125.1(11) . . ? F2' C26 F1'' 139.1(18) . . ? F2'' C26 F1'' 107.0(14) . . ? F1 C26 F1'' 30.3(11) . . ? F2' C26 F3' 109.8(19) . . ? F2'' C26 F3' 135.8(16) . . ? F1 C26 F3' 39.4(15) . . ? F1'' C26 F3' 69.7(17) . . ? F2' C26 F1' 113.9(18) . . ? F2'' C26 F1' 71.6(16) . . ? F1 C26 F1' 70.2(13) . . ? F1'' C26 F1' 40.7(13) . . ? F3' C26 F1' 109.0(16) . . ? F2' C26 F3 33.6(18) . . ? F2'' C26 F3 74.3(12) . . ? F1 C26 F3 109.0(6) . . ? F1'' C26 F3 131.9(11) . . ? F3' C26 F3 77.2(14) . . ? F1' C26 F3 135.1(13) . . ? F2' C26 F2 71.5(18) . . ? F2'' C26 F2 28.2(11) . . ? F1 C26 F2 106.3(5) . . ? F1'' C26 F2 81.7(13) . . ? F3' C26 F2 135.9(13) . . ? F1' C26 F2 43.7(15) . . ? F3 C26 F2 100.3(5) . . ? F2' C26 F3'' 70.6(19) . . ? F2'' C26 F3'' 108.3(13) . . ? F1 C26 F3'' 77.8(10) . . ? F1'' C26 F3'' 107.1(12) . . ? F3' C26 F3'' 41.1(14) . . ? F1' C26 F3'' 138.0(12) . . ? F3 C26 F3'' 37.0(8) . . ? F2 C26 F3'' 129.1(9) . . ? F2' C26 C15 108.1(15) . . ? F2'' C26 C15 113.2(11) . . ? F1 C26 C15 114.8(5) . . ? F1'' C26 C15 110.4(11) . . ? F3' C26 C15 108.7(11) . . ? F1' C26 C15 107.2(10) . . ? F3 C26 C15 112.6(4) . . ? F2 C26 C15 112.6(5) . . ? F3'' C26 C15 110.6(7) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.225 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.051 data_10d _database_code_depnum_ccdc_archive 'CCDC 914094' #TrackingRef '10d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Bis-(3,5-di-trifluromethylbenzo-1-yl)-benzo[1,2-b:6,5-b']dithiophene-4,5-dione ; _chemical_name_common ; 2,7-Bis-(3,5-di-trifluromethylbenzo-1-yl)-benzo[1,2-b:6,5-b']dithiophene-4,5-dione ; _chemical_melting_point ? _chemical_formula_moiety 'C28 H8 F12 O4 S2' _chemical_formula_sum 'C28 H8 F12 O4 S2' _chemical_formula_weight 700.46 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.659(7) _cell_length_b 16.482(9) _cell_length_c 22.503(13) _cell_angle_alpha 75.532(11) _cell_angle_beta 89.384(13) _cell_angle_gamma 87.650(11) _cell_volume 4184(4) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3675 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 25.59 _exptl_crystal_description plates _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.668 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2088 _exptl_absorpt_coefficient_mu 0.307 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.929 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22378 _diffrn_reflns_av_R_equivalents 0.1203 _diffrn_reflns_av_sigmaI/netI 0.2011 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 25.00 _reflns_number_total 14504 _reflns_number_gt 8173 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.1745P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 14504 _refine_ls_number_parameters 1243 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1776 _refine_ls_R_factor_gt 0.0974 _refine_ls_wR_factor_ref 0.3094 _refine_ls_wR_factor_gt 0.2338 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 S1A S 0.84723(14) 0.01249(10) 0.59924(7) 0.0244(4) Uani 1 1 d . . . S2A S 0.86457(14) 0.05324(10) 0.43760(7) 0.0243(4) Uani 1 1 d . . . F1A F 1.1962(4) 0.1203(3) 0.8216(3) 0.0657(17) Uani 1 1 d . . . F2A F 1.1037(5) 0.2043(3) 0.8673(2) 0.0585(14) Uani 1 1 d . . . F3A F 1.0983(4) 0.2267(3) 0.7676(2) 0.0518(14) Uani 1 1 d . . . F4A F 0.7074(5) 0.0413(4) 0.9617(2) 0.0712(17) Uani 1 1 d . . . F5A F 0.8693(4) -0.0231(4) 0.9992(2) 0.0674(18) Uani 1 1 d . . . F6A F 0.7476(4) -0.0848(3) 0.9565(2) 0.0573(14) Uani 1 1 d . . . F7A F 0.5980(4) 0.3612(3) 0.2268(2) 0.0484(12) Uani 1 1 d . . . F8A F 0.5528(4) 0.3420(3) 0.1388(2) 0.0469(12) Uani 1 1 d . . . F9A F 0.6858(4) 0.4271(2) 0.1430(2) 0.0449(12) Uani 1 1 d . . . F10A F 0.8894(6) 0.2307(3) 0.0259(2) 0.077(2) Uani 1 1 d . . . F11A F 0.9138(6) 0.1002(3) 0.0780(2) 0.0688(17) Uani 1 1 d . . . F12A F 1.0435(6) 0.1896(4) 0.0808(3) 0.0759(18) Uani 1 1 d . . . O1A O 0.8065(5) -0.0752(3) 0.7328(2) 0.0366(13) Uani 1 1 d . . . O2A O 0.9080(4) 0.0296(3) 0.3131(2) 0.0322(12) Uani 1 1 d . . . O3A O 0.8485(4) 0.3559(3) 0.4406(2) 0.0322(12) Uani 1 1 d . . . O4A O 0.7663(4) 0.3214(3) 0.5624(2) 0.0323(12) Uani 1 1 d . . . C1A C 0.8323(6) 0.0573(4) 0.6616(3) 0.0220(14) Uani 1 1 d . . . C2A C 0.8171(5) 0.1445(4) 0.6432(3) 0.0198(14) Uani 1 1 d . . . H2A H 0.8069 0.1795 0.6708 0.024 Uiso 1 1 calc R . . C3A C 0.8186(5) 0.1752(4) 0.5772(3) 0.0231(14) Uani 1 1 d . . . C4A C 0.8356(5) 0.1109(4) 0.5471(3) 0.0215(14) Uani 1 1 d . . . C5A C 0.8472(5) 0.1272(4) 0.4796(3) 0.0240(15) Uani 1 1 d . . . C6A C 0.8427(6) 0.2095(4) 0.4416(3) 0.0251(15) Uani 1 1 d . . . C7A C 0.8341(6) 0.2833(4) 0.4697(3) 0.0270(16) Uani 1 1 d . . . C8A C 0.8038(6) 0.2634(4) 0.5399(3) 0.0270(16) Uani 1 1 d . . . C9A C 0.8317(5) -0.0005(4) 0.7255(3) 0.0268(16) Uani 1 1 d . . . C10A C 0.8663(6) 0.0316(4) 0.7791(3) 0.0273(16) Uani 1 1 d . . . C11A C 0.9559(6) 0.0876(4) 0.7736(3) 0.0280(16) Uani 1 1 d . . . H11A H 0.9907 0.1095 0.7348 0.034 Uiso 1 1 calc R . . C12A C 0.9937(6) 0.1110(4) 0.8261(3) 0.0279(16) Uani 1 1 d . . . C13A C 0.9410(6) 0.0809(5) 0.8841(3) 0.0337(18) Uani 1 1 d . . . H13A H 0.9656 0.0983 0.9189 0.040 Uiso 1 1 calc R . . C14A C 0.8509(6) 0.0244(5) 0.8889(3) 0.0340(18) Uani 1 1 d . . . C15A C 0.8143(6) -0.0009(4) 0.8368(3) 0.0298(17) Uani 1 1 d . . . H15A H 0.7550 -0.0397 0.8405 0.036 Uiso 1 1 calc R . . C16A C 1.0962(6) 0.1655(5) 0.8212(3) 0.0353(18) Uani 1 1 d . . . C17A C 0.7953(7) -0.0089(6) 0.9511(4) 0.045(2) Uani 1 1 d . . . C18A C 0.8531(5) 0.2118(4) 0.3786(3) 0.0268(16) Uani 1 1 d . . . H18A H 0.8521 0.2622 0.3469 0.032 Uiso 1 1 calc R . . C19A C 0.8649(6) 0.1322(4) 0.3680(3) 0.0247(15) Uani 1 1 d . . . C20A C 0.8745(6) 0.1026(4) 0.3107(3) 0.0270(16) Uani 1 1 d . . . C21A C 0.8443(6) 0.1629(4) 0.2482(3) 0.0325(18) Uani 1 1 d . . . C22A C 0.7611(6) 0.2303(4) 0.2413(3) 0.0264(16) Uani 1 1 d . . . H22A H 0.7240 0.2413 0.2765 0.032 Uiso 1 1 calc R . . C23A C 0.7334(6) 0.2814(4) 0.1817(3) 0.0274(16) Uani 1 1 d . . . C24A C 0.7883(6) 0.2666(5) 0.1291(3) 0.0345(18) Uani 1 1 d . . . H24A H 0.7701 0.3013 0.0896 0.041 Uiso 1 1 calc R . . C25A C 0.8709(7) 0.1995(5) 0.1355(3) 0.0356(18) Uani 1 1 d . . . C26A C 0.8986(6) 0.1483(4) 0.1958(3) 0.0325(17) Uani 1 1 d . . . H26A H 0.9548 0.1038 0.2001 0.039 Uiso 1 1 calc R . . C27A C 0.6436(6) 0.3537(4) 0.1735(3) 0.0316(17) Uani 1 1 d . . . C28A C 0.9291(8) 0.1807(5) 0.0801(4) 0.050(2) Uani 1 1 d . . . S1B S 0.56553(14) 0.63857(10) 0.42648(7) 0.0254(4) Uani 1 1 d . . . S2B S 0.35508(14) 0.65447(10) 0.31207(7) 0.0273(4) Uani 1 1 d . . . F1B F 0.9150(4) 0.5580(3) 0.76108(19) 0.0469(12) Uani 1 1 d . . . F2B F 1.0781(4) 0.5983(3) 0.71753(19) 0.0418(11) Uani 1 1 d . . . F3B F 0.9246(4) 0.6820(3) 0.6966(2) 0.0449(12) Uani 1 1 d . . . F4B F 1.1381(4) 0.3617(3) 0.6194(2) 0.0467(12) Uani 1 1 d . . . F5B F 0.9768(4) 0.2999(2) 0.64476(18) 0.0358(10) Uani 1 1 d . . . F6B F 1.0211(4) 0.3487(3) 0.54775(18) 0.0364(10) Uani 1 1 d . . . F7B F 0.4547(5) 0.5128(4) 0.0738(2) 0.078(2) Uani 1 1 d . . . F8B F 0.3354(6) 0.4733(4) 0.0145(3) 0.087(2) Uani 1 1 d . . . F9B F 0.3901(5) 0.5986(3) -0.0092(2) 0.0630(15) Uani 1 1 d . . . F10B F -0.1192(5) 0.5295(4) 0.0826(3) 0.0756(19) Uani 1 1 d . . . F11B F -0.0674(4) 0.6081(3) -0.0056(2) 0.0569(14) Uani 1 1 d . . . F12B F -0.1324(4) 0.6650(4) 0.0658(3) 0.079(2) Uani 1 1 d . . . O1B O 0.7116(4) 0.6863(3) 0.5108(2) 0.0337(12) Uani 1 1 d . . . O2B O 0.1584(5) 0.7150(4) 0.2235(2) 0.0464(15) Uani 1 1 d . . . O3B O 0.5865(5) 0.3299(3) 0.4371(2) 0.0374(13) Uani 1 1 d . . . O4B O 0.4363(5) 0.3460(3) 0.3389(2) 0.0392(13) Uani 1 1 d . . . C1B C 0.6632(6) 0.5686(4) 0.4768(3) 0.0260(15) Uani 1 1 d . . . C2B C 0.6554(6) 0.4873(4) 0.4736(3) 0.0240(15) Uani 1 1 d . . . H2B H 0.6993 0.4416 0.4982 0.029 Uiso 1 1 calc R . . C3B C 0.5724(6) 0.4790(4) 0.4281(3) 0.0238(14) Uani 1 1 d . . . C4B C 0.5199(6) 0.5570(4) 0.3990(3) 0.0248(15) Uani 1 1 d . . . C5B C 0.4344(5) 0.5634(4) 0.3491(3) 0.0235(14) Uani 1 1 d . . . C6B C 0.4098(6) 0.4954(4) 0.3259(3) 0.0277(16) Uani 1 1 d . . . C7B C 0.4612(6) 0.4089(4) 0.3548(3) 0.0283(16) Uani 1 1 d . . . C8B C 0.5484(6) 0.3998(4) 0.4099(3) 0.0268(16) Uani 1 1 d . . . C9B C 0.7323(6) 0.6099(4) 0.5160(3) 0.0263(16) Uani 1 1 d . . . C10B C 0.8238(6) 0.5629(4) 0.5622(3) 0.0288(16) Uani 1 1 d . . . C11B C 0.8811(6) 0.4862(4) 0.5587(3) 0.0277(16) Uani 1 1 d . . . H11B H 0.8640 0.4604 0.5266 0.033 Uiso 1 1 calc R . . C12B C 0.9644(6) 0.4489(4) 0.6042(3) 0.0289(16) Uani 1 1 d . . . C13B C 0.9904(6) 0.4855(4) 0.6518(3) 0.0289(16) Uani 1 1 d . . . H13B H 1.0449 0.4590 0.6823 0.035 Uiso 1 1 calc R . . C14B C 0.9345(6) 0.5632(4) 0.6543(3) 0.0275(16) Uani 1 1 d . . . C15B C 0.8505(6) 0.6010(4) 0.6099(3) 0.0263(15) Uani 1 1 d . . . H15B H 0.8119 0.6520 0.6122 0.032 Uiso 1 1 calc R . . C16B C 0.9627(6) 0.6005(5) 0.7072(3) 0.0356(19) Uani 1 1 d . . . C17B C 1.0245(6) 0.3647(4) 0.6040(3) 0.0293(16) Uani 1 1 d . . . C18B C 0.3329(6) 0.5178(4) 0.2739(3) 0.0281(16) Uani 1 1 d . . . H18B H 0.3102 0.4800 0.2510 0.034 Uiso 1 1 calc R . . C19B C 0.2963(6) 0.6020(4) 0.2614(3) 0.0285(16) Uani 1 1 d . . . C20B C 0.2095(6) 0.6517(5) 0.2149(3) 0.0292(16) Uani 1 1 d . . . C21B C 0.1878(6) 0.6187(4) 0.1584(3) 0.0312(17) Uani 1 1 d . . . C22B C 0.2801(6) 0.5889(4) 0.1280(3) 0.0310(17) Uani 1 1 d . . . H22B H 0.3558 0.5859 0.1439 0.037 Uiso 1 1 calc R . . C23B C 0.2598(6) 0.5638(5) 0.0744(3) 0.0337(17) Uani 1 1 d . . . C24B C 0.1476(7) 0.5689(5) 0.0501(3) 0.0358(18) Uani 1 1 d . . . H24B H 0.1347 0.5520 0.0134 0.043 Uiso 1 1 calc R . . C25B C 0.0556(7) 0.5987(4) 0.0801(3) 0.0347(18) Uani 1 1 d . . . C26B C 0.0761(6) 0.6260(5) 0.1337(3) 0.0330(17) Uani 1 1 d . . . H26B H 0.0147 0.6491 0.1531 0.040 Uiso 1 1 calc R . . C27B C 0.3605(7) 0.5366(5) 0.0388(3) 0.0389(19) Uani 1 1 d . . . C28B C -0.0650(7) 0.6019(6) 0.0558(4) 0.044(2) Uani 1 1 d . . . S1C S 0.53947(13) 0.11123(10) 0.46638(7) 0.0238(4) Uani 1 1 d . . . S2C S 0.52608(14) 0.11742(10) 0.62090(7) 0.0252(4) Uani 1 1 d . . . F1C F 0.2935(4) 0.3595(3) 0.1884(2) 0.0565(14) Uani 1 1 d . . . F2C F 0.1664(4) 0.2678(3) 0.1930(2) 0.0569(14) Uani 1 1 d . . . F3C F 0.2620(5) 0.3123(3) 0.1092(2) 0.0684(17) Uani 1 1 d . . . F4C F 0.4853(4) 0.0350(3) 0.10010(19) 0.0460(12) Uani 1 1 d . . . F5C F 0.6184(4) 0.1275(3) 0.08526(19) 0.0428(11) Uani 1 1 d . . . F6C F 0.6391(4) 0.0103(3) 0.1579(2) 0.0527(13) Uani 1 1 d . . . F7C F 0.2723(5) 0.4245(3) 0.6998(2) 0.0581(14) Uani 1 1 d . . . F8C F 0.1818(6) 0.4128(4) 0.7844(3) 0.093(2) Uani 1 1 d . . . F9C F 0.3426(7) 0.4746(4) 0.7678(4) 0.105(3) Uani 1 1 d . . . F10C F 0.4840(5) 0.1285(3) 0.9714(2) 0.0587(15) Uani 1 1 d . . . F11C F 0.4241(6) 0.2519(5) 0.9783(2) 0.090(2) Uani 1 1 d . . . F12C F 0.5985(5) 0.2318(4) 0.9488(2) 0.074(2) Uani 1 1 d . . . O1C O 0.6284(4) 0.0790(3) 0.3536(2) 0.0344(12) Uani 1 1 d . . . O2C O 0.5873(4) 0.0969(3) 0.7534(2) 0.0355(12) Uani 1 1 d . . . O3C O 0.1127(4) 0.1654(3) 0.4628(2) 0.0341(12) Uani 1 1 d . . . O4C O 0.1018(4) 0.1658(3) 0.5876(2) 0.0306(12) Uani 1 1 d . . . C1C C 0.4608(6) 0.1235(4) 0.3974(3) 0.0252(15) Uani 1 1 d . . . C2C C 0.3436(6) 0.1387(4) 0.4064(3) 0.0258(16) Uani 1 1 d . . . H2C H 0.2878 0.1480 0.3748 0.031 Uiso 1 1 calc R . . C3C C 0.3175(5) 0.1386(4) 0.4683(3) 0.0225(14) Uani 1 1 d . . . C4C C 0.4166(6) 0.1260(4) 0.5060(3) 0.0227(15) Uani 1 1 d . . . C5C C 0.4104(5) 0.1289(4) 0.5709(3) 0.0201(14) Uani 1 1 d . . . C6C C 0.3079(6) 0.1462(4) 0.5997(3) 0.0234(15) Uani 1 1 d . . . C7C C 0.1958(5) 0.1559(4) 0.5637(3) 0.0224(14) Uani 1 1 d . . . C8C C 0.2012(6) 0.1552(4) 0.4935(3) 0.0257(15) Uani 1 1 d . . . C9C C 0.5288(6) 0.1110(4) 0.3442(3) 0.0262(15) Uani 1 1 d . . . C10C C 0.4826(6) 0.1352(4) 0.2782(3) 0.0263(16) Uani 1 1 d . . . C11C C 0.3962(6) 0.2000(4) 0.2566(3) 0.0256(15) Uani 1 1 d . . . H11C H 0.3612 0.2292 0.2840 0.031 Uiso 1 1 calc R . . C12C C 0.3635(6) 0.2200(4) 0.1939(3) 0.0274(16) Uani 1 1 d . . . C13C C 0.4150(6) 0.1775(4) 0.1531(3) 0.0266(16) Uani 1 1 d . . . H13C H 0.3913 0.1905 0.1114 0.032 Uiso 1 1 calc R . . C14C C 0.5027(6) 0.1148(4) 0.1744(3) 0.0297(16) Uani 1 1 d . . . C15C C 0.5354(6) 0.0931(4) 0.2370(3) 0.0267(16) Uani 1 1 d . . . H15C H 0.5929 0.0503 0.2512 0.032 Uiso 1 1 calc R . . C16C C 0.5602(7) 0.0722(5) 0.1293(3) 0.0350(18) Uani 1 1 d . . . C17C C 0.2706(6) 0.2899(4) 0.1710(3) 0.0334(18) Uani 1 1 d . . . C18C C 0.3222(6) 0.1511(4) 0.6607(3) 0.0239(14) Uani 1 1 d . . . H18C H 0.2610 0.1618 0.6863 0.029 Uiso 1 1 calc R . . C19C C 0.4373(6) 0.1384(4) 0.6795(3) 0.0282(16) Uani 1 1 d . . . C20C C 0.4967(6) 0.1393(4) 0.7383(3) 0.0265(16) Uani 1 1 d . . . C21C C 0.4493(6) 0.1961(4) 0.7777(3) 0.0277(16) Uani 1 1 d . . . C22C C 0.3824(6) 0.2712(4) 0.7519(3) 0.0250(15) Uani 1 1 d . . . H22C H 0.3590 0.2838 0.7102 0.030 Uiso 1 1 calc R . . C23C C 0.3518(6) 0.3261(4) 0.7885(3) 0.0286(16) Uani 1 1 d . . . C24C C 0.3844(6) 0.3072(5) 0.8514(3) 0.0345(18) Uani 1 1 d . . . H24C H 0.3627 0.3443 0.8762 0.041 Uiso 1 1 calc R . . C25C C 0.4499(6) 0.2319(5) 0.8767(3) 0.0330(17) Uani 1 1 d . . . C26C C 0.4845(6) 0.1777(5) 0.8406(3) 0.0328(17) Uani 1 1 d . . . H26C H 0.5312 0.1290 0.8577 0.039 Uiso 1 1 calc R . . C27C C 0.2856(6) 0.4067(5) 0.7612(3) 0.0339(17) Uani 1 1 d . . . C28C C 0.4905(7) 0.2113(5) 0.9441(3) 0.044(2) 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 S1A 0.0303(9) 0.0162(8) 0.0230(8) 0.0033(6) -0.0112(7) -0.0065(7) S2A 0.0298(8) 0.0191(9) 0.0207(8) 0.0017(6) -0.0110(7) -0.0028(7) F1A 0.027(2) 0.042(3) 0.127(5) -0.019(3) -0.024(3) -0.003(2) F2A 0.070(3) 0.063(3) 0.046(3) -0.017(2) -0.009(2) -0.031(3) F3A 0.051(3) 0.042(3) 0.056(3) 0.006(2) -0.025(2) -0.024(2) F4A 0.070(4) 0.082(4) 0.050(3) -0.001(3) 0.013(3) 0.018(3) F5A 0.055(3) 0.107(5) 0.029(2) 0.009(3) -0.019(2) -0.027(3) F6A 0.059(3) 0.069(4) 0.036(3) 0.004(2) -0.008(2) -0.020(3) F7A 0.060(3) 0.042(3) 0.037(2) 0.001(2) -0.001(2) 0.011(2) F8A 0.036(2) 0.043(3) 0.053(3) 0.004(2) -0.018(2) -0.006(2) F9A 0.053(3) 0.017(2) 0.056(3) 0.0067(19) -0.006(2) -0.003(2) F10A 0.127(5) 0.064(4) 0.027(2) 0.006(2) -0.007(3) 0.044(4) F11A 0.107(5) 0.052(3) 0.046(3) -0.014(2) -0.004(3) 0.021(3) F12A 0.073(4) 0.094(5) 0.057(3) -0.014(3) 0.014(3) 0.003(4) O1A 0.047(3) 0.022(3) 0.033(3) 0.009(2) -0.013(2) -0.014(2) O2A 0.044(3) 0.022(3) 0.029(2) -0.0037(19) -0.013(2) 0.006(2) O3A 0.038(3) 0.016(2) 0.036(3) 0.008(2) -0.010(2) -0.008(2) O4A 0.047(3) 0.021(3) 0.025(2) 0.0006(19) -0.010(2) 0.003(2) C1A 0.030(3) 0.016(3) 0.021(3) -0.003(2) -0.006(3) -0.008(3) C2A 0.020(3) 0.016(3) 0.021(3) 0.001(2) -0.002(2) -0.005(3) C3A 0.023(3) 0.021(3) 0.023(3) -0.001(3) -0.007(3) 0.002(3) C4A 0.022(3) 0.020(3) 0.020(3) 0.002(2) -0.005(2) -0.005(3) C5A 0.020(3) 0.023(4) 0.024(3) 0.003(3) -0.012(3) -0.002(3) C6A 0.026(3) 0.020(3) 0.025(3) 0.002(3) -0.011(3) -0.003(3) C7A 0.026(3) 0.026(4) 0.025(3) 0.002(3) -0.013(3) -0.008(3) C8A 0.032(4) 0.020(4) 0.027(3) -0.001(3) -0.011(3) -0.005(3) C9A 0.018(3) 0.029(4) 0.026(3) 0.010(3) -0.008(3) -0.009(3) C10A 0.028(3) 0.023(4) 0.026(3) 0.003(3) -0.016(3) -0.004(3) C11A 0.024(3) 0.024(4) 0.029(3) 0.006(3) -0.009(3) -0.003(3) C12A 0.033(4) 0.021(4) 0.028(3) -0.003(3) -0.015(3) 0.000(3) C13A 0.031(4) 0.035(4) 0.035(4) -0.008(3) -0.017(3) 0.006(3) C14A 0.028(4) 0.037(4) 0.031(4) 0.002(3) -0.017(3) -0.004(3) C15A 0.028(3) 0.031(4) 0.024(3) 0.005(3) -0.007(3) -0.005(3) C16A 0.031(4) 0.038(4) 0.035(4) -0.005(3) -0.014(3) -0.002(3) C17A 0.041(4) 0.053(5) 0.034(4) 0.003(4) -0.016(4) -0.012(4) C18A 0.023(3) 0.025(4) 0.028(3) 0.005(3) -0.008(3) -0.007(3) C19A 0.029(3) 0.024(4) 0.019(3) 0.002(3) -0.009(3) -0.011(3) C20A 0.024(3) 0.027(4) 0.028(3) -0.001(3) -0.008(3) -0.007(3) C21A 0.041(4) 0.029(4) 0.023(3) 0.003(3) -0.017(3) -0.008(3) C22A 0.027(3) 0.022(4) 0.025(3) 0.004(3) -0.009(3) -0.009(3) C23A 0.031(4) 0.020(3) 0.026(3) 0.004(3) -0.009(3) -0.005(3) C24A 0.036(4) 0.031(4) 0.029(4) 0.009(3) -0.009(3) -0.004(3) C25A 0.052(5) 0.029(4) 0.021(3) 0.003(3) -0.008(3) -0.001(4) C26A 0.037(4) 0.025(4) 0.029(4) 0.006(3) -0.006(3) 0.005(3) C27A 0.038(4) 0.020(4) 0.031(4) 0.005(3) -0.001(3) -0.007(3) C28A 0.067(6) 0.035(5) 0.038(4) 0.006(4) -0.003(4) 0.009(4) S1B 0.0312(9) 0.0156(8) 0.0257(8) 0.0029(6) -0.0106(7) -0.0043(7) S2B 0.0285(9) 0.0224(9) 0.0276(8) 0.0005(7) -0.0093(7) -0.0021(7) F1B 0.055(3) 0.052(3) 0.031(2) -0.001(2) -0.007(2) -0.019(2) F2B 0.039(2) 0.041(3) 0.042(2) -0.0009(19) -0.0181(19) -0.015(2) F3B 0.056(3) 0.029(2) 0.049(3) -0.0060(19) -0.025(2) -0.001(2) F4B 0.032(2) 0.041(3) 0.066(3) -0.010(2) -0.015(2) 0.006(2) F5B 0.043(2) 0.025(2) 0.032(2) 0.0079(17) -0.0029(18) -0.0006(19) F6B 0.042(2) 0.032(2) 0.030(2) 0.0018(17) -0.0011(18) 0.005(2) F7B 0.062(3) 0.121(5) 0.044(3) -0.013(3) -0.014(3) 0.053(4) F8B 0.082(5) 0.084(5) 0.111(5) -0.050(4) 0.031(4) -0.014(4) F9B 0.065(3) 0.065(3) 0.045(3) 0.012(2) 0.013(2) 0.012(3) F10B 0.062(4) 0.093(5) 0.068(4) -0.008(3) -0.017(3) -0.040(4) F11B 0.055(3) 0.071(3) 0.045(3) -0.013(2) -0.026(2) -0.012(3) F12B 0.044(3) 0.116(5) 0.093(4) -0.063(4) -0.041(3) 0.025(3) O1B 0.041(3) 0.022(3) 0.036(3) -0.002(2) -0.016(2) -0.001(2) O2B 0.047(3) 0.051(4) 0.041(3) -0.012(3) -0.021(3) 0.012(3) O3B 0.044(3) 0.022(3) 0.042(3) 0.001(2) -0.015(2) -0.004(2) O4B 0.056(3) 0.024(3) 0.037(3) -0.005(2) -0.016(3) -0.007(3) C1B 0.032(4) 0.012(3) 0.030(3) 0.003(3) -0.007(3) -0.007(3) C2B 0.027(3) 0.018(3) 0.023(3) 0.005(3) -0.007(3) -0.013(3) C3B 0.028(3) 0.020(3) 0.021(3) 0.000(3) -0.004(3) -0.006(3) C4B 0.026(3) 0.023(4) 0.022(3) 0.001(3) -0.001(3) -0.002(3) C5B 0.025(3) 0.019(3) 0.024(3) 0.001(3) -0.004(3) -0.008(3) C6B 0.025(3) 0.028(4) 0.029(3) -0.003(3) -0.004(3) -0.006(3) C7B 0.025(3) 0.026(4) 0.027(3) 0.007(3) -0.004(3) -0.013(3) C8B 0.029(4) 0.016(3) 0.033(4) 0.001(3) -0.007(3) -0.010(3) C9B 0.026(3) 0.019(4) 0.027(3) 0.010(3) -0.002(3) -0.009(3) C10B 0.028(4) 0.028(4) 0.025(3) 0.006(3) -0.009(3) -0.010(3) C11B 0.024(3) 0.019(3) 0.035(4) 0.006(3) -0.008(3) -0.008(3) C12B 0.034(4) 0.022(4) 0.027(3) 0.003(3) -0.005(3) -0.003(3) C13B 0.023(3) 0.026(4) 0.033(4) 0.003(3) -0.007(3) -0.006(3) C14B 0.020(3) 0.023(4) 0.034(4) 0.003(3) -0.004(3) -0.008(3) C15B 0.028(3) 0.019(3) 0.028(3) 0.001(3) 0.002(3) -0.007(3) C16B 0.037(4) 0.032(4) 0.032(4) 0.004(3) -0.014(3) -0.015(3) C17B 0.031(4) 0.021(4) 0.032(4) 0.001(3) -0.006(3) 0.005(3) C18B 0.033(4) 0.027(4) 0.022(3) -0.001(3) -0.005(3) -0.010(3) C19B 0.025(3) 0.030(4) 0.026(3) 0.003(3) -0.001(3) -0.013(3) C20B 0.022(3) 0.037(4) 0.027(3) -0.003(3) -0.006(3) -0.002(3) C21B 0.035(4) 0.029(4) 0.025(3) 0.001(3) -0.007(3) -0.004(3) C22B 0.026(3) 0.032(4) 0.027(3) 0.009(3) -0.008(3) -0.007(3) C23B 0.039(4) 0.030(4) 0.026(4) 0.004(3) -0.001(3) 0.000(3) C24B 0.047(4) 0.034(4) 0.023(3) -0.002(3) -0.010(3) 0.002(4) C25B 0.042(4) 0.026(4) 0.033(4) 0.001(3) -0.019(3) -0.007(3) C26B 0.032(4) 0.033(4) 0.031(4) -0.003(3) 0.001(3) -0.001(3) C27B 0.041(4) 0.037(5) 0.034(4) 0.000(3) -0.005(3) 0.000(4) C28B 0.036(4) 0.058(6) 0.044(5) -0.027(4) -0.013(4) -0.006(4) S1C 0.0244(8) 0.0236(9) 0.0211(8) -0.0003(6) -0.0096(6) -0.0047(7) S2C 0.0245(8) 0.0261(9) 0.0221(8) 0.0001(6) -0.0123(6) -0.0019(7) F1C 0.060(3) 0.027(3) 0.080(4) -0.010(2) -0.027(3) 0.005(2) F2C 0.037(3) 0.044(3) 0.076(3) 0.009(2) -0.012(2) 0.001(2) F3C 0.088(4) 0.065(3) 0.039(3) 0.007(2) -0.021(3) 0.040(3) F4C 0.061(3) 0.041(3) 0.035(2) -0.007(2) -0.020(2) -0.011(2) F5C 0.050(3) 0.044(3) 0.036(2) -0.012(2) 0.000(2) -0.009(2) F6C 0.064(3) 0.059(3) 0.034(2) -0.014(2) -0.020(2) 0.028(3) F7C 0.073(3) 0.047(3) 0.042(3) 0.008(2) -0.009(2) 0.021(3) F8C 0.078(4) 0.091(5) 0.073(4) 0.040(3) 0.032(3) 0.048(4) F9C 0.120(6) 0.037(3) 0.156(7) -0.018(4) -0.095(5) -0.004(4) F10C 0.073(3) 0.066(3) 0.029(2) 0.006(2) -0.019(2) -0.018(3) F11C 0.115(5) 0.120(5) 0.037(3) -0.029(3) -0.023(3) 0.047(5) F12C 0.081(4) 0.085(4) 0.045(3) 0.009(3) -0.040(3) -0.043(3) O1C 0.026(2) 0.044(3) 0.029(2) 0.000(2) -0.011(2) -0.006(2) O2C 0.037(3) 0.037(3) 0.030(3) -0.005(2) -0.016(2) 0.009(2) O3C 0.027(2) 0.037(3) 0.037(3) -0.006(2) -0.015(2) -0.004(2) O4C 0.027(3) 0.030(3) 0.034(3) -0.003(2) -0.010(2) -0.008(2) C1C 0.031(4) 0.020(3) 0.021(3) 0.004(3) -0.017(3) -0.008(3) C2C 0.030(4) 0.011(3) 0.032(3) 0.006(3) -0.010(3) -0.011(3) C3C 0.022(3) 0.019(3) 0.024(3) 0.001(3) -0.005(3) -0.008(3) C4C 0.030(3) 0.011(3) 0.027(3) -0.002(2) -0.014(3) -0.004(3) C5C 0.023(3) 0.008(3) 0.027(3) 0.000(2) -0.006(3) -0.004(3) C6C 0.027(3) 0.014(3) 0.026(3) 0.003(3) -0.013(3) -0.005(3) C7C 0.018(3) 0.016(3) 0.030(3) 0.000(3) -0.005(3) -0.003(3) C8C 0.030(4) 0.014(3) 0.031(3) 0.000(3) -0.012(3) -0.005(3) C9C 0.032(4) 0.016(3) 0.028(3) -0.001(3) -0.012(3) -0.008(3) C10C 0.028(3) 0.025(4) 0.022(3) 0.003(3) -0.009(3) -0.007(3) C11C 0.028(3) 0.027(4) 0.020(3) -0.002(3) -0.002(3) -0.008(3) C12C 0.030(4) 0.025(4) 0.024(3) -0.001(3) -0.010(3) -0.006(3) C13C 0.035(4) 0.021(3) 0.020(3) 0.004(3) -0.011(3) -0.007(3) C14C 0.036(4) 0.026(4) 0.024(3) 0.001(3) -0.007(3) -0.009(3) C15C 0.029(3) 0.023(4) 0.024(3) 0.004(3) -0.012(3) -0.004(3) C16C 0.042(4) 0.034(4) 0.025(3) 0.001(3) -0.014(3) -0.001(4) C17C 0.040(4) 0.023(4) 0.034(4) -0.002(3) -0.011(3) -0.005(3) C18C 0.023(3) 0.019(3) 0.027(3) 0.001(3) -0.003(3) -0.008(3) C19C 0.031(4) 0.022(4) 0.025(3) 0.008(3) -0.011(3) -0.005(3) C20C 0.028(3) 0.019(3) 0.027(3) 0.005(3) -0.008(3) -0.003(3) C21C 0.024(3) 0.030(4) 0.027(3) -0.002(3) -0.011(3) -0.002(3) C22C 0.027(3) 0.021(3) 0.024(3) 0.001(3) -0.014(3) -0.004(3) C23C 0.033(4) 0.025(4) 0.027(3) -0.004(3) -0.013(3) -0.004(3) C24C 0.032(4) 0.043(4) 0.029(4) -0.009(3) -0.010(3) 0.000(3) C25C 0.039(4) 0.036(4) 0.025(3) -0.008(3) -0.007(3) -0.003(3) C26C 0.032(4) 0.031(4) 0.031(4) 0.003(3) -0.008(3) -0.004(3) C27C 0.036(4) 0.033(4) 0.037(4) -0.017(3) -0.008(3) 0.008(3) C28C 0.047(5) 0.049(5) 0.032(4) -0.003(4) -0.012(4) 0.004(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 S1A C1A 1.746(7) . ? S1A C4A 1.749(6) . ? S2A C5A 1.723(7) . ? S2A C19A 1.769(6) . ? F1A C16A 1.357(9) . ? F2A C16A 1.353(9) . ? F3A C16A 1.366(8) . ? F4A C17A 1.348(11) . ? F5A C17A 1.360(8) . ? F6A C17A 1.366(10) . ? F7A C27A 1.339(9) . ? F8A C27A 1.371(8) . ? F9A C27A 1.342(8) . ? F10A C28A 1.362(8) . ? F11A C28A 1.359(11) . ? F12A C28A 1.349(11) . ? O1A C9A 1.248(8) . ? O2A C20A 1.237(9) . ? O3A C7A 1.229(8) . ? O4A C8A 1.251(9) . ? C1A C2A 1.397(9) . ? C1A C9A 1.514(8) . ? C2A C3A 1.446(8) . ? C2A H2A 0.9500 . ? C3A C4A 1.398(9) . ? C3A C8A 1.491(9) . ? C4A C5A 1.481(9) . ? C5A C6A 1.411(8) . ? C6A C18A 1.413(9) . ? C6A C7A 1.503(10) . ? C7A C8A 1.571(10) . ? C9A C10A 1.497(10) . ? C10A C11A 1.406(10) . ? C10A C15A 1.415(10) . ? C11A C12A 1.411(9) . ? C11A H11A 0.9500 . ? C12A C13A 1.418(11) . ? C12A C16A 1.511(10) . ? C13A C14A 1.418(10) . ? C13A H13A 0.9500 . ? C14A C15A 1.416(10) . ? C14A C17A 1.517(11) . ? C15A H15A 0.9500 . ? C18A C19A 1.392(10) . ? C18A H18A 0.9500 . ? C19A C20A 1.491(10) . ? C20A C21A 1.541(8) . ? C21A C26A 1.400(11) . ? C21A C22A 1.425(10) . ? C22A C23A 1.426(8) . ? C22A H22A 0.9500 . ? C23A C24A 1.410(11) . ? C23A C27A 1.530(10) . ? C24A C25A 1.416(11) . ? C24A H24A 0.9500 . ? C25A C26A 1.440(8) . ? C25A C28A 1.506(12) . ? C26A H26A 0.9500 . ? S1B C4B 1.719(7) . ? S1B C1B 1.783(6) . ? S2B C19B 1.753(7) . ? S2B C5B 1.755(6) . ? F1B C16B 1.365(9) . ? F2B C16B 1.365(8) . ? F3B C16B 1.361(9) . ? F4B C17B 1.368(8) . ? F5B C17B 1.357(8) . ? F6B C17B 1.358(8) . ? F7B C27B 1.345(8) . ? F8B C27B 1.338(10) . ? F9B C27B 1.342(9) . ? F10B C28B 1.371(10) . ? F11B C28B 1.361(9) . ? F12B C28B 1.340(10) . ? O1B C9B 1.248(8) . ? O2B C20B 1.237(9) . ? O3B C8B 1.229(8) . ? O4B C7B 1.226(9) . ? C1B C2B 1.366(9) . ? C1B C9B 1.501(9) . ? C2B C3B 1.452(8) . ? C2B H2B 0.9500 . ? C3B C4B 1.406(9) . ? C3B C8B 1.500(9) . ? C4B C5B 1.491(8) . ? C5B C6B 1.390(10) . ? C6B C18B 1.447(8) . ? C6B C7B 1.513(9) . ? C7B C8B 1.585(8) . ? C9B C10B 1.541(8) . ? C10B C15B 1.415(10) . ? C10B C11B 1.426(11) . ? C11B C12B 1.425(8) . ? C11B H11B 0.9500 . ? C12B C13B 1.396(10) . ? C12B C17B 1.529(10) . ? C13B C14B 1.426(10) . ? C13B H13B 0.9500 . ? C14B C15B 1.415(8) . ? C14B C16B 1.515(11) . ? C15B H15B 0.9500 . ? C18B C19B 1.395(10) . ? C18B H18B 0.9500 . ? C19B C20B 1.522(8) . ? C20B C21B 1.530(10) . ? C21B C22B 1.405(11) . ? C21B C26B 1.409(9) . ? C22B C23B 1.395(11) . ? C22B H22B 0.9500 . ? C23B C24B 1.415(10) . ? C23B C27B 1.529(12) . ? C24B C25B 1.397(12) . ? C24B H24B 0.9500 . ? C25B C26B 1.415(11) . ? C25B C28B 1.509(10) . ? C26B H26B 0.9500 . ? S1C C4C 1.720(8) . ? S1C C1C 1.775(6) . ? S2C C5C 1.740(6) . ? S2C C19C 1.761(8) . ? F1C C17C 1.338(9) . ? F2C C17C 1.337(9) . ? F3C C17C 1.350(8) . ? F4C C16C 1.351(8) . ? F5C C16C 1.364(9) . ? F6C C16C 1.381(8) . ? F7C C27C 1.348(8) . ? F8C C27C 1.322(10) . ? F9C C27C 1.364(9) . ? F10C C28C 1.355(9) . ? F11C C28C 1.357(11) . ? F12C C28C 1.329(10) . ? O1C C9C 1.253(8) . ? O2C C20C 1.245(8) . ? O3C C8C 1.231(7) . ? O4C C7C 1.237(8) . ? C1C C2C 1.401(10) . ? C1C C9C 1.480(10) . ? C2C C3C 1.421(10) . ? C2C H2C 0.9500 . ? C3C C4C 1.418(8) . ? C3C C8C 1.506(10) . ? C4C C5C 1.475(9) . ? C5C C6C 1.406(10) . ? C6C C18C 1.409(9) . ? C6C C7C 1.526(8) . ? C7C C8C 1.583(9) . ? C9C C10C 1.536(8) . ? C10C C15C 1.412(10) . ? C10C C11C 1.433(9) . ? C11C C12C 1.419(8) . ? C11C H11C 0.9500 . ? C12C C13C 1.404(10) . ? C12C C17C 1.543(9) . ? C13C C14C 1.420(9) . ? C13C H13C 0.9500 . ? C14C C15C 1.416(8) . ? C14C C16C 1.509(11) . ? C15C H15C 0.9500 . ? C18C C19C 1.403(9) . ? C18C H18C 0.9500 . ? C19C C20C 1.503(9) . ? C20C C21C 1.526(10) . ? C21C C22C 1.432(9) . ? C21C C26C 1.433(9) . ? C22C C23C 1.401(10) . ? C22C H22C 0.9500 . ? C23C C24C 1.424(9) . ? C23C C27C 1.503(9) . ? C24C C25C 1.424(10) . ? C24C H24C 0.9500 . ? C25C C26C 1.394(11) . ? C25C C28C 1.544(9) . ? C26C H26C 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1A S1A C4A 91.6(3) . . ? C5A S2A C19A 91.3(3) . . ? C2A C1A C9A 129.5(6) . . ? C2A C1A S1A 112.2(4) . . ? C9A C1A S1A 118.2(5) . . ? C1A C2A C3A 111.8(6) . . ? C1A C2A H2A 124.1 . . ? C3A C2A H2A 124.1 . . ? C4A C3A C2A 112.7(5) . . ? C4A C3A C8A 119.1(6) . . ? C2A C3A C8A 128.2(6) . . ? C3A C4A C5A 122.7(5) . . ? C3A C4A S1A 111.6(4) . . ? C5A C4A S1A 125.7(5) . . ? C6A C5A C4A 121.4(6) . . ? C6A C5A S2A 111.8(5) . . ? C4A C5A S2A 126.8(5) . . ? C5A C6A C18A 112.9(6) . . ? C5A C6A C7A 120.1(6) . . ? C18A C6A C7A 126.9(5) . . ? O3A C7A C6A 123.5(6) . . ? O3A C7A C8A 120.3(6) . . ? C6A C7A C8A 116.2(5) . . ? O4A C8A C3A 122.2(6) . . ? O4A C8A C7A 119.3(5) . . ? C3A C8A C7A 118.5(6) . . ? O1A C9A C10A 120.6(5) . . ? O1A C9A C1A 119.7(6) . . ? C10A C9A C1A 119.6(6) . . ? C11A C10A C15A 120.3(6) . . ? C11A C10A C9A 120.6(6) . . ? C15A C10A C9A 118.8(6) . . ? C10A C11A C12A 119.4(7) . . ? C10A C11A H11A 120.3 . . ? C12A C11A H11A 120.3 . . ? C11A C12A C13A 121.3(7) . . ? C11A C12A C16A 119.4(6) . . ? C13A C12A C16A 119.2(6) . . ? C12A C13A C14A 118.5(7) . . ? C12A C13A H13A 120.7 . . ? C14A C13A H13A 120.7 . . ? C15A C14A C13A 120.5(7) . . ? C15A C14A C17A 120.7(7) . . ? C13A C14A C17A 118.8(7) . . ? C10A C15A C14A 119.9(7) . . ? C10A C15A H15A 120.1 . . ? C14A C15A H15A 120.1 . . ? F2A C16A F1A 106.3(5) . . ? F2A C16A F3A 106.7(6) . . ? F1A C16A F3A 104.8(6) . . ? F2A C16A C12A 113.9(7) . . ? F1A C16A C12A 111.5(6) . . ? F3A C16A C12A 113.0(5) . . ? F4A C17A F5A 108.3(7) . . ? F4A C17A F6A 104.3(7) . . ? F5A C17A F6A 103.8(6) . . ? F4A C17A C14A 112.6(6) . . ? F5A C17A C14A 114.2(7) . . ? F6A C17A C14A 112.8(7) . . ? C19A C18A C6A 112.7(5) . . ? C19A C18A H18A 123.7 . . ? C6A C18A H18A 123.7 . . ? C18A C19A C20A 132.6(6) . . ? C18A C19A S2A 111.3(5) . . ? C20A C19A S2A 116.1(5) . . ? O2A C20A C19A 120.0(6) . . ? O2A C20A C21A 119.7(6) . . ? C19A C20A C21A 120.2(6) . . ? C26A C21A C22A 119.1(6) . . ? C26A C21A C20A 118.0(6) . . ? C22A C21A C20A 122.9(7) . . ? C21A C22A C23A 120.1(7) . . ? C21A C22A H22A 120.0 . . ? C23A C22A H22A 120.0 . . ? C24A C23A C22A 120.7(6) . . ? C24A C23A C27A 118.5(5) . . ? C22A C23A C27A 120.8(6) . . ? C23A C24A C25A 119.6(6) . . ? C23A C24A H24A 120.2 . . ? C25A C24A H24A 120.2 . . ? C24A C25A C26A 119.4(7) . . ? C24A C25A C28A 120.9(6) . . ? C26A C25A C28A 119.7(7) . . ? C21A C26A C25A 121.2(7) . . ? C21A C26A H26A 119.4 . . ? C25A C26A H26A 119.4 . . ? F7A C27A F9A 109.8(6) . . ? F7A C27A F8A 105.5(6) . . ? F9A C27A F8A 104.9(5) . . ? F7A C27A C23A 112.6(5) . . ? F9A C27A C23A 112.1(6) . . ? F8A C27A C23A 111.5(6) . . ? F12A C28A F11A 106.3(8) . . ? F12A C28A F10A 106.9(7) . . ? F11A C28A F10A 106.8(7) . . ? F12A C28A C25A 112.0(7) . . ? F11A C28A C25A 111.0(7) . . ? F10A C28A C25A 113.4(7) . . ? C4B S1B C1B 90.2(3) . . ? C19B S2B C5B 90.9(3) . . ? C2B C1B C9B 133.3(5) . . ? C2B C1B S1B 112.8(4) . . ? C9B C1B S1B 113.9(5) . . ? C1B C2B C3B 112.1(5) . . ? C1B C2B H2B 124.0 . . ? C3B C2B H2B 124.0 . . ? C4B C3B C2B 111.5(6) . . ? C4B C3B C8B 122.5(5) . . ? C2B C3B C8B 125.9(5) . . ? C3B C4B C5B 120.4(6) . . ? C3B C4B S1B 113.5(5) . . ? C5B C4B S1B 126.1(5) . . ? C6B C5B C4B 122.3(6) . . ? C6B C5B S2B 112.0(4) . . ? C4B C5B S2B 125.7(5) . . ? C5B C6B C18B 112.8(6) . . ? C5B C6B C7B 120.7(6) . . ? C18B C6B C7B 126.5(6) . . ? O4B C7B C6B 123.3(6) . . ? O4B C7B C8B 119.0(6) . . ? C6B C7B C8B 117.7(6) . . ? O3B C8B C3B 124.1(6) . . ? O3B C8B C7B 119.7(6) . . ? C3B C8B C7B 116.1(5) . . ? O1B C9B C1B 117.0(5) . . ? O1B C9B C10B 119.5(6) . . ? C1B C9B C10B 123.6(6) . . ? C15B C10B C11B 120.2(5) . . ? C15B C10B C9B 115.9(6) . . ? C11B C10B C9B 123.9(6) . . ? C12B C11B C10B 118.6(7) . . ? C12B C11B H11B 120.7 . . ? C10B C11B H11B 120.7 . . ? C13B C12B C11B 121.6(7) . . ? C13B C12B C17B 117.7(6) . . ? C11B C12B C17B 120.6(6) . . ? C12B C13B C14B 119.4(6) . . ? C12B C13B H13B 120.3 . . ? C14B C13B H13B 120.3 . . ? C15B C14B C13B 120.0(6) . . ? C15B C14B C16B 121.7(7) . . ? C13B C14B C16B 118.2(5) . . ? C14B C15B C10B 120.2(7) . . ? C14B C15B H15B 119.9 . . ? C10B C15B H15B 119.9 . . ? F3B C16B F2B 107.3(6) . . ? F3B C16B F1B 107.4(7) . . ? F2B C16B F1B 106.0(5) . . ? F3B C16B C14B 111.6(5) . . ? F2B C16B C14B 112.0(7) . . ? F1B C16B C14B 112.2(6) . . ? F5B C17B F6B 107.8(5) . . ? F5B C17B F4B 106.2(5) . . ? F6B C17B F4B 106.2(6) . . ? F5B C17B C12B 112.1(6) . . ? F6B C17B C12B 111.7(5) . . ? F4B C17B C12B 112.5(6) . . ? C19B C18B C6B 111.6(6) . . ? C19B C18B H18B 124.2 . . ? C6B C18B H18B 124.2 . . ? C18B C19B C20B 130.4(6) . . ? C18B C19B S2B 112.6(5) . . ? C20B C19B S2B 116.9(5) . . ? O2B C20B C19B 120.8(6) . . ? O2B C20B C21B 122.3(6) . . ? C19B C20B C21B 117.0(6) . . ? C22B C21B C26B 120.4(7) . . ? C22B C21B C20B 120.1(6) . . ? C26B C21B C20B 119.2(7) . . ? C23B C22B C21B 119.5(6) . . ? C23B C22B H22B 120.3 . . ? C21B C22B H22B 120.3 . . ? C22B C23B C24B 120.6(7) . . ? C22B C23B C27B 119.9(6) . . ? C24B C23B C27B 119.3(7) . . ? C25B C24B C23B 120.0(7) . . ? C25B C24B H24B 120.0 . . ? C23B C24B H24B 120.0 . . ? C24B C25B C26B 119.6(6) . . ? C24B C25B C28B 120.6(7) . . ? C26B C25B C28B 119.9(8) . . ? C21B C26B C25B 119.9(7) . . ? C21B C26B H26B 120.1 . . ? C25B C26B H26B 120.1 . . ? F8B C27B F9B 104.8(7) . . ? F8B C27B F7B 107.6(7) . . ? F9B C27B F7B 107.3(7) . . ? F8B C27B C23B 112.5(7) . . ? F9B C27B C23B 111.6(6) . . ? F7B C27B C23B 112.5(6) . . ? F12B C28B F11B 106.9(6) . . ? F12B C28B F10B 106.3(8) . . ? F11B C28B F10B 105.6(6) . . ? F12B C28B C25B 114.4(7) . . ? F11B C28B C25B 112.4(7) . . ? F10B C28B C25B 110.6(7) . . ? C4C S1C C1C 91.4(3) . . ? C5C S2C C19C 91.7(3) . . ? C2C C1C C9C 133.4(5) . . ? C2C C1C S1C 111.2(5) . . ? C9C C1C S1C 115.2(5) . . ? C1C C2C C3C 112.5(5) . . ? C1C C2C H2C 123.7 . . ? C3C C2C H2C 123.7 . . ? C4C C3C C2C 112.6(6) . . ? C4C C3C C8C 120.8(6) . . ? C2C C3C C8C 126.5(5) . . ? C3C C4C C5C 121.7(6) . . ? C3C C4C S1C 112.2(5) . . ? C5C C4C S1C 126.0(4) . . ? C6C C5C C4C 123.2(5) . . ? C6C C5C S2C 110.8(5) . . ? C4C C5C S2C 125.9(5) . . ? C5C C6C C18C 114.0(5) . . ? C5C C6C C7C 118.8(6) . . ? C18C C6C C7C 127.3(6) . . ? O4C C7C C6C 122.0(6) . . ? O4C C7C C8C 119.5(5) . . ? C6C C7C C8C 118.5(6) . . ? O3C C8C C3C 123.0(6) . . ? O3C C8C C7C 120.2(6) . . ? C3C C8C C7C 116.7(5) . . ? O1C C9C C1C 118.4(5) . . ? O1C C9C C10C 118.6(6) . . ? C1C C9C C10C 122.9(6) . . ? C15C C10C C11C 120.0(6) . . ? C15C C10C C9C 116.1(6) . . ? C11C C10C C9C 123.8(6) . . ? C12C C11C C10C 119.2(7) . . ? C12C C11C H11C 120.4 . . ? C10C C11C H11C 120.4 . . ? C13C C12C C11C 120.9(6) . . ? C13C C12C C17C 120.2(6) . . ? C11C C12C C17C 118.9(7) . . ? C12C C13C C14C 119.7(6) . . ? C12C C13C H13C 120.2 . . ? C14C C13C H13C 120.2 . . ? C15C C14C C13C 120.3(7) . . ? C15C C14C C16C 120.8(6) . . ? C13C C14C C16C 118.9(6) . . ? C10C C15C C14C 120.0(6) . . ? C10C C15C H15C 120.0 . . ? C14C C15C H15C 120.0 . . ? F4C C16C F5C 107.1(5) . . ? F4C C16C F6C 106.6(6) . . ? F5C C16C F6C 106.8(6) . . ? F4C C16C C14C 113.0(6) . . ? F5C C16C C14C 111.5(6) . . ? F6C C16C C14C 111.6(5) . . ? F2C C17C F1C 106.5(7) . . ? F2C C17C F3C 107.0(6) . . ? F1C C17C F3C 106.6(6) . . ? F2C C17C C12C 112.5(6) . . ? F1C C17C C12C 111.3(5) . . ? F3C C17C C12C 112.5(6) . . ? C19C C18C C6C 112.3(6) . . ? C19C C18C H18C 123.9 . . ? C6C C18C H18C 123.9 . . ? C18C C19C C20C 132.9(7) . . ? C18C C19C S2C 111.2(5) . . ? C20C C19C S2C 115.9(5) . . ? O2C C20C C19C 120.1(7) . . ? O2C C20C C21C 119.9(6) . . ? C19C C20C C21C 119.8(5) . . ? C22C C21C C26C 119.8(7) . . ? C22C C21C C20C 121.8(5) . . ? C26C C21C C20C 118.1(6) . . ? C23C C22C C21C 119.6(6) . . ? C23C C22C H22C 120.2 . . ? C21C C22C H22C 120.2 . . ? C22C C23C C24C 120.8(6) . . ? C22C C23C C27C 120.0(5) . . ? C24C C23C C27C 119.2(7) . . ? C25C C24C C23C 119.0(7) . . ? C25C C24C H24C 120.5 . . ? C23C C24C H24C 120.5 . . ? C26C C25C C24C 121.1(6) . . ? C26C C25C C28C 118.5(6) . . ? C24C C25C C28C 120.2(7) . . ? C25C C26C C21C 119.6(6) . . ? C25C C26C H26C 120.2 . . ? C21C C26C H26C 120.2 . . ? F8C C27C F7C 106.3(6) . . ? F8C C27C F9C 106.7(8) . . ? F7C C27C F9C 101.5(7) . . ? F8C C27C C23C 114.9(7) . . ? F7C C27C C23C 114.8(6) . . ? F9C C27C C23C 111.6(6) . . ? F12C C28C F10C 107.4(6) . . ? F12C C28C F11C 107.8(8) . . ? F10C C28C F11C 106.0(7) . . ? F12C C28C C25C 112.1(7) . . ? F10C C28C C25C 111.5(7) . . ? F11C C28C C25C 111.7(6) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.245 _refine_diff_density_min -1.144 _refine_diff_density_rms 0.160 data_16a _database_code_depnum_ccdc_archive 'CCDC 914095' #TrackingRef '16a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Bis-(pentafluorobenzoyl)-benzo[1,2-d:4,3-d']bis(thiazole)-4,5-bis-(1,3-dioxolane) ; _chemical_name_common ; 2,7-Bis-(pentafluorobenzoyl)-benzo[1,2-d:4,3-d']bis(thiazole)-4,5-bis-(1,3-dioxolane) ; _chemical_melting_point ? _chemical_formula_moiety 'C26 H8 F10 N2 O6 S2' _chemical_formula_sum 'C26 H8 F10 N2 O6 S2' _chemical_formula_weight 698.46 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' N N 0.0061 0.0033 '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 _symmetry_space_group_name_Hall -P2ybc 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 14.6242(10) _cell_length_b 17.9041(13) _cell_length_c 21.1195(15) _cell_angle_alpha 90.00 _cell_angle_beta 109.0980(10) _cell_angle_gamma 90.00 _cell_volume 5225.4(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9865 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 31.37 _exptl_crystal_description plates _exptl_crystal_colour orange _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2784 _exptl_absorpt_coefficient_mu 0.324 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9840 _exptl_absorpt_correction_T_max 0.9968 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 49699 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 26.00 _reflns_number_total 10272 _reflns_number_gt 8353 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0393P)^2^+3.3031P] 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 10272 _refine_ls_number_parameters 829 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0875 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.002 _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 S1A S 0.18793(3) 0.21132(3) 0.29806(2) 0.02189(11) Uani 1 1 d . . . S2A S -0.06339(4) 0.23559(3) 0.20373(2) 0.02497(12) Uani 1 1 d . . . F1A F 0.56785(9) 0.21586(7) 0.36408(6) 0.0338(3) Uani 1 1 d . . . F2A F 0.71811(9) 0.29702(9) 0.43777(7) 0.0525(4) Uani 1 1 d . . . F3A F 0.69486(11) 0.39974(9) 0.52571(7) 0.0578(4) Uani 1 1 d . . . F4A F 0.52025(12) 0.41584(8) 0.54375(7) 0.0535(4) Uani 1 1 d . . . F5A F 0.36927(9) 0.33214(8) 0.47146(6) 0.0386(3) Uani 1 1 d . . . F6A F -0.15864(8) 0.34963(7) 0.01892(6) 0.0354(3) Uani 1 1 d . . . F7A F -0.25832(10) 0.44377(8) -0.07777(6) 0.0418(3) Uani 1 1 d . . . F8A F -0.44337(9) 0.47883(7) -0.09141(6) 0.0377(3) Uani 1 1 d . . . F9A F -0.52928(8) 0.42095(7) -0.00649(6) 0.0303(3) Uani 1 1 d . . . F10A F -0.43220(8) 0.32527(7) 0.08966(6) 0.0300(3) Uani 1 1 d . . . O1A O 0.38854(11) 0.15954(8) 0.36711(8) 0.0338(4) Uani 1 1 d . . . O2A O -0.27425(10) 0.22533(8) 0.12388(8) 0.0341(4) Uani 1 1 d . . . O3A O 0.21789(9) 0.48332(7) 0.26925(7) 0.0226(3) Uani 1 1 d . . . O4A O 0.12044(10) 0.45270(7) 0.33088(6) 0.0220(3) Uani 1 1 d . . . O5A O 0.00823(10) 0.50381(7) 0.21162(7) 0.0254(3) Uani 1 1 d . . . O6A O 0.08863(10) 0.43950(7) 0.15244(7) 0.0260(3) Uani 1 1 d . . . N1A N 0.27942(11) 0.33747(9) 0.32579(8) 0.0203(3) Uani 1 1 d . . . N2A N -0.10068(11) 0.37091(9) 0.15968(8) 0.0233(4) Uani 1 1 d . . . C1A C 0.29019(14) 0.26527(10) 0.33511(9) 0.0214(4) Uani 1 1 d . . . C2A C 0.18664(13) 0.35298(10) 0.28783(9) 0.0188(4) Uani 1 1 d . . . C3A C 0.12648(14) 0.29214(10) 0.26858(9) 0.0200(4) Uani 1 1 d . . . C4A C 0.02628(14) 0.30155(10) 0.22857(9) 0.0205(4) Uani 1 1 d . . . C5A C -0.00750(14) 0.36978(10) 0.20122(9) 0.0212(4) Uani 1 1 d . . . C6A C 0.05793(14) 0.43704(10) 0.20947(9) 0.0212(4) Uani 1 1 d . . . C7A C 0.14767(13) 0.43218(10) 0.27473(9) 0.0199(4) Uani 1 1 d . . . C8A C 0.24456(15) 0.52871(12) 0.32866(11) 0.0298(5) Uani 1 1 d . . . H8A1 H 0.2612 0.5801 0.3191 0.036 Uiso 1 1 calc R . . H8A2 H 0.3001 0.5069 0.3643 0.036 Uiso 1 1 calc R . . C9A C 0.15463(15) 0.52780(11) 0.34817(11) 0.0270(4) Uani 1 1 d . . . H9A1 H 0.1696 0.5374 0.3967 0.032 Uiso 1 1 calc R . . H9A2 H 0.1069 0.5650 0.3224 0.032 Uiso 1 1 calc R . . C10A C -0.01033(18) 0.53949(13) 0.14788(12) 0.0395(6) Uani 1 1 d . . . H10A H -0.0114 0.5945 0.1521 0.047 Uiso 1 1 calc R . . H10B H -0.0726 0.5227 0.1155 0.047 Uiso 1 1 calc R . . C11A C 0.07284(19) 0.51468(12) 0.12724(12) 0.0380(6) Uani 1 1 d . . . H11A H 0.0564 0.5158 0.0779 0.046 Uiso 1 1 calc R . . H11B H 0.1305 0.5463 0.1478 0.046 Uiso 1 1 calc R . . C12A C 0.38086(14) 0.22651(11) 0.37193(9) 0.0226(4) Uani 1 1 d . . . C13A C 0.46330(14) 0.27308(11) 0.41425(9) 0.0223(4) Uani 1 1 d . . . C14A C 0.55421(15) 0.26463(11) 0.40832(10) 0.0260(4) Uani 1 1 d . . . C15A C 0.63184(15) 0.30645(14) 0.44542(11) 0.0339(5) Uani 1 1 d . . . C16A C 0.61962(17) 0.35825(13) 0.49012(11) 0.0375(6) Uani 1 1 d . . . C17A C 0.53105(18) 0.36705(12) 0.49847(10) 0.0354(5) Uani 1 1 d . . . C18A C 0.45377(15) 0.32454(12) 0.46072(10) 0.0272(4) Uani 1 1 d . . . C19A C -0.13903(14) 0.30458(11) 0.15623(10) 0.0240(4) Uani 1 1 d . . . C20A C -0.23785(14) 0.28368(11) 0.11473(10) 0.0263(4) Uani 1 1 d . . . C21A C -0.29075(14) 0.33726(11) 0.05986(10) 0.0244(4) Uani 1 1 d . . . C22A C -0.24881(14) 0.36816(11) 0.01569(10) 0.0266(4) Uani 1 1 d . . . C23A C -0.29972(16) 0.41580(12) -0.03491(10) 0.0285(5) Uani 1 1 d . . . C24A C -0.39401(15) 0.43353(11) -0.04212(10) 0.0271(5) Uani 1 1 d . . . C25A C -0.43803(14) 0.40364(11) 0.00063(10) 0.0239(4) Uani 1 1 d . . . C26A C -0.38671(14) 0.35506(11) 0.05038(9) 0.0226(4) Uani 1 1 d . . . S1B S 0.55335(4) 0.17566(3) 0.20051(2) 0.02393(11) Uani 1 1 d . . . S2B S 0.79496(4) 0.20475(3) 0.32250(3) 0.02758(12) Uani 1 1 d . . . F1B F 0.17042(9) 0.18858(7) 0.14266(6) 0.0326(3) Uani 1 1 d . . . F2B F 0.02766(9) 0.28507(8) 0.08327(7) 0.0450(4) Uani 1 1 d . . . F3B F 0.05901(11) 0.39874(9) 0.00767(7) 0.0553(4) Uani 1 1 d . . . F4B F 0.23003(12) 0.40905(8) -0.01591(7) 0.0515(4) Uani 1 1 d . . . F5B F 0.37070(9) 0.30910(7) 0.03886(6) 0.0381(3) Uani 1 1 d . . . F6B F 0.89627(9) 0.34271(8) 0.49781(7) 0.0437(3) Uani 1 1 d . . . F7B F 0.99585(10) 0.45075(8) 0.58018(7) 0.0441(3) Uani 1 1 d . . . F8B F 1.16572(9) 0.49924(7) 0.57085(6) 0.0387(3) Uani 1 1 d . . . F9B F 1.24391(9) 0.43261(7) 0.48582(6) 0.0335(3) Uani 1 1 d . . . F10B F 1.15349(9) 0.31498(7) 0.41189(6) 0.0334(3) Uani 1 1 d . . . O1B O 0.34403(11) 0.12552(8) 0.12267(7) 0.0318(3) Uani 1 1 d . . . O2B O 1.00807(13) 0.20594(9) 0.40490(9) 0.0539(5) Uani 1 1 d . . . O3B O 0.55672(10) 0.39400(7) 0.31407(7) 0.0268(3) Uani 1 1 d . . . O4B O 0.51944(10) 0.44756(7) 0.21042(7) 0.0259(3) Uani 1 1 d . . . O5B O 0.69825(10) 0.41467(7) 0.19977(7) 0.0262(3) Uani 1 1 d . . . O6B O 0.70970(10) 0.47243(7) 0.29876(7) 0.0281(3) Uani 1 1 d . . . N1B N 0.45442(11) 0.29789(9) 0.18458(8) 0.0221(3) Uani 1 1 d . . . N2B N 0.83351(12) 0.34586(9) 0.34096(8) 0.0250(4) Uani 1 1 d . . . C1B C 0.44742(14) 0.22699(10) 0.16863(9) 0.0225(4) Uani 1 1 d . . . C2B C 0.54600(14) 0.31437(10) 0.22322(9) 0.0213(4) Uani 1 1 d . . . C3B C 0.61021(14) 0.25590(10) 0.23781(9) 0.0220(4) Uani 1 1 d . . . C4B C 0.70898(14) 0.26806(11) 0.28025(9) 0.0231(4) Uani 1 1 d . . . C5B C 0.74291(14) 0.33976(11) 0.29645(9) 0.0228(4) Uani 1 1 d . . . C6B C 0.68268(15) 0.40631(10) 0.26256(9) 0.0239(4) Uani 1 1 d . . . C7B C 0.57445(14) 0.39172(10) 0.25185(9) 0.0227(4) Uani 1 1 d . . . C8B C 0.49898(17) 0.45952(12) 0.31340(11) 0.0354(5) Uani 1 1 d . . . H8B1 H 0.5400 0.5031 0.3333 0.042 Uiso 1 1 calc R . . H8B2 H 0.4524 0.4507 0.3377 0.042 Uiso 1 1 calc R . . C9B C 0.44764(17) 0.47031(13) 0.23915(11) 0.0369(5) Uani 1 1 d . . . H9B1 H 0.3891 0.4386 0.2231 0.044 Uiso 1 1 calc R . . H9B2 H 0.4290 0.5232 0.2286 0.044 Uiso 1 1 calc R . . C10B C 0.72074(19) 0.49218(12) 0.19380(12) 0.0375(5) Uani 1 1 d . . . H10C H 0.6618 0.5213 0.1705 0.045 Uiso 1 1 calc R . . H10D H 0.7680 0.4980 0.1696 0.045 Uiso 1 1 calc R . . C11B C 0.7636(2) 0.51536(13) 0.26603(13) 0.0452(6) Uani 1 1 d . . . H11C H 0.8334 0.5031 0.2839 0.054 Uiso 1 1 calc R . . H11D H 0.7551 0.5696 0.2714 0.054 Uiso 1 1 calc R . . C12B C 0.35582(14) 0.19230(11) 0.12751(10) 0.0242(4) Uani 1 1 d . . . C13B C 0.27601(14) 0.24692(11) 0.09389(10) 0.0240(4) Uani 1 1 d . . . C14B C 0.18723(15) 0.24237(12) 0.10356(10) 0.0267(4) Uani 1 1 d . . . C15B C 0.11360(16) 0.29273(13) 0.07470(10) 0.0329(5) Uani 1 1 d . . . C16B C 0.12935(17) 0.34955(13) 0.03552(11) 0.0369(6) Uani 1 1 d . . . C17B C 0.21580(18) 0.35491(12) 0.02390(11) 0.0360(5) Uani 1 1 d . . . C18B C 0.28848(16) 0.30376(12) 0.05294(11) 0.0300(5) Uani 1 1 d . . . C19B C 0.86975(15) 0.27937(11) 0.35899(10) 0.0263(4) Uani 1 1 d . . . C20B C 0.96862(16) 0.26546(12) 0.40465(11) 0.0330(5) Uani 1 1 d . . . C21B C 1.01990(15) 0.32840(11) 0.44946(10) 0.0266(4) Uani 1 1 d . . . C22B C 0.98149(14) 0.36416(12) 0.49330(11) 0.0294(5) Uani 1 1 d . . . C23B C 1.03181(15) 0.41943(12) 0.53578(10) 0.0301(5) Uani 1 1 d . . . C24B C 1.11945(15) 0.44300(11) 0.53254(10) 0.0272(5) Uani 1 1 d . . . C25B C 1.15952(14) 0.40879(11) 0.48939(10) 0.0251(4) Uani 1 1 d . . . C26B C 1.11086(15) 0.35047(11) 0.45037(9) 0.0246(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1A 0.0220(2) 0.0162(2) 0.0218(2) -0.00075(18) -0.00060(19) 0.00044(18) S2A 0.0227(2) 0.0182(2) 0.0258(3) 0.00234(19) -0.0033(2) -0.00383(19) F1A 0.0293(7) 0.0414(7) 0.0316(7) 0.0014(6) 0.0112(5) 0.0056(6) F2A 0.0240(7) 0.0840(11) 0.0476(9) 0.0067(8) 0.0090(6) -0.0122(7) F3A 0.0529(9) 0.0662(10) 0.0385(8) -0.0035(7) -0.0066(7) -0.0347(8) F4A 0.0699(11) 0.0489(9) 0.0327(8) -0.0195(7) 0.0044(7) -0.0078(8) F5A 0.0339(7) 0.0481(8) 0.0329(7) -0.0099(6) 0.0099(6) 0.0069(6) F6A 0.0233(6) 0.0470(8) 0.0348(7) 0.0041(6) 0.0079(5) 0.0042(6) F7A 0.0449(8) 0.0533(8) 0.0335(7) 0.0136(6) 0.0214(6) 0.0062(7) F8A 0.0413(8) 0.0418(7) 0.0278(7) 0.0160(6) 0.0085(6) 0.0131(6) F9A 0.0247(6) 0.0342(7) 0.0291(6) 0.0022(5) 0.0049(5) 0.0052(5) F10A 0.0255(6) 0.0380(7) 0.0235(6) 0.0060(5) 0.0040(5) -0.0060(5) O1A 0.0290(8) 0.0214(8) 0.0425(9) -0.0011(6) -0.0002(7) 0.0030(6) O2A 0.0282(8) 0.0275(8) 0.0367(9) 0.0065(6) -0.0029(7) -0.0078(6) O3A 0.0229(7) 0.0188(7) 0.0243(7) -0.0032(5) 0.0052(6) -0.0062(5) O4A 0.0262(7) 0.0167(6) 0.0219(7) -0.0027(5) 0.0064(6) -0.0018(5) O5A 0.0263(7) 0.0173(7) 0.0274(7) 0.0038(6) 0.0019(6) 0.0033(6) O6A 0.0318(8) 0.0241(7) 0.0195(7) 0.0022(6) 0.0050(6) -0.0046(6) N1A 0.0211(8) 0.0199(8) 0.0172(8) -0.0009(6) 0.0029(7) 0.0002(6) N2A 0.0200(8) 0.0232(8) 0.0218(8) 0.0023(7) 0.0001(7) -0.0010(7) C1A 0.0206(10) 0.0217(10) 0.0188(9) -0.0020(7) 0.0020(8) -0.0010(8) C2A 0.0199(9) 0.0186(9) 0.0157(9) -0.0007(7) 0.0029(7) 0.0002(7) C3A 0.0217(10) 0.0182(9) 0.0171(9) 0.0002(7) 0.0023(8) 0.0011(7) C4A 0.0210(10) 0.0180(9) 0.0186(9) -0.0002(7) 0.0010(8) -0.0018(8) C5A 0.0211(10) 0.0210(9) 0.0182(9) -0.0001(7) 0.0019(8) -0.0013(8) C6A 0.0228(10) 0.0177(9) 0.0197(9) 0.0003(7) 0.0022(8) -0.0005(8) C7A 0.0206(10) 0.0178(9) 0.0189(9) -0.0005(7) 0.0034(8) -0.0027(7) C8A 0.0297(11) 0.0240(10) 0.0320(11) -0.0096(9) 0.0049(9) -0.0073(9) C9A 0.0320(11) 0.0171(9) 0.0288(11) -0.0063(8) 0.0059(9) -0.0020(8) C10A 0.0440(14) 0.0287(12) 0.0406(13) 0.0183(10) 0.0070(11) 0.0045(10) C11A 0.0541(15) 0.0260(11) 0.0319(12) 0.0102(9) 0.0113(11) -0.0037(10) C12A 0.0233(10) 0.0226(10) 0.0194(9) 0.0010(8) 0.0035(8) 0.0011(8) C13A 0.0203(10) 0.0230(10) 0.0193(9) 0.0045(8) 0.0004(8) 0.0017(8) C14A 0.0275(11) 0.0280(10) 0.0192(10) 0.0078(8) 0.0029(8) 0.0020(9) C15A 0.0220(11) 0.0487(14) 0.0277(11) 0.0111(10) 0.0037(9) -0.0062(10) C16A 0.0342(13) 0.0419(13) 0.0251(11) 0.0044(10) -0.0058(10) -0.0169(10) C17A 0.0479(14) 0.0314(12) 0.0193(10) -0.0036(9) 0.0005(10) -0.0049(10) C18A 0.0261(11) 0.0293(11) 0.0215(10) 0.0016(8) 0.0015(8) 0.0024(9) C19A 0.0231(10) 0.0212(10) 0.0218(10) 0.0022(8) -0.0004(8) -0.0004(8) C20A 0.0232(10) 0.0253(10) 0.0243(10) 0.0009(8) -0.0006(8) -0.0020(8) C21A 0.0235(10) 0.0237(10) 0.0200(10) 0.0002(8) -0.0014(8) -0.0032(8) C22A 0.0221(10) 0.0293(11) 0.0257(11) -0.0016(8) 0.0040(8) -0.0001(8) C23A 0.0346(12) 0.0316(11) 0.0215(10) 0.0026(8) 0.0122(9) -0.0014(9) C24A 0.0333(12) 0.0254(10) 0.0185(10) 0.0040(8) 0.0028(9) 0.0058(9) C25A 0.0232(10) 0.0245(10) 0.0200(10) -0.0026(8) 0.0020(8) 0.0007(8) C26A 0.0249(10) 0.0238(10) 0.0155(9) -0.0012(8) 0.0019(8) -0.0057(8) S1B 0.0223(2) 0.0178(2) 0.0252(3) -0.00118(19) -0.0011(2) -0.00007(19) S2B 0.0263(3) 0.0190(2) 0.0275(3) 0.0002(2) -0.0047(2) 0.0020(2) F1B 0.0325(7) 0.0381(7) 0.0271(6) -0.0012(5) 0.0094(5) -0.0042(5) F2B 0.0285(7) 0.0666(10) 0.0380(8) -0.0104(7) 0.0084(6) 0.0115(7) F3B 0.0585(10) 0.0623(10) 0.0337(8) 0.0039(7) -0.0005(7) 0.0382(8) F4B 0.0668(10) 0.0379(8) 0.0400(8) 0.0188(6) 0.0042(7) 0.0081(7) F5B 0.0303(7) 0.0413(7) 0.0381(7) 0.0125(6) 0.0050(6) -0.0059(6) F6B 0.0209(6) 0.0531(9) 0.0549(9) -0.0058(7) 0.0093(6) -0.0003(6) F7B 0.0387(8) 0.0571(9) 0.0380(8) -0.0153(6) 0.0147(6) 0.0106(7) F8B 0.0362(7) 0.0358(7) 0.0338(7) -0.0160(6) -0.0025(6) -0.0001(6) F9B 0.0284(7) 0.0352(7) 0.0354(7) 0.0026(5) 0.0085(5) -0.0010(5) F10B 0.0432(7) 0.0335(7) 0.0247(6) -0.0028(5) 0.0126(6) 0.0096(6) O1B 0.0302(8) 0.0219(8) 0.0352(8) -0.0002(6) -0.0003(7) -0.0038(6) O2B 0.0422(10) 0.0313(9) 0.0596(12) -0.0164(8) -0.0222(9) 0.0147(8) O3B 0.0354(8) 0.0226(7) 0.0202(7) 0.0008(6) 0.0062(6) 0.0049(6) O4B 0.0290(8) 0.0193(7) 0.0231(7) 0.0039(5) 0.0002(6) 0.0055(6) O5B 0.0326(8) 0.0199(7) 0.0235(7) 0.0018(5) 0.0055(6) -0.0036(6) O6B 0.0330(8) 0.0175(7) 0.0264(7) -0.0040(6) -0.0003(6) -0.0036(6) N1B 0.0217(8) 0.0213(8) 0.0190(8) 0.0015(6) 0.0008(7) -0.0001(7) N2B 0.0238(9) 0.0216(8) 0.0227(9) -0.0007(7) -0.0019(7) 0.0007(7) C1B 0.0222(10) 0.0211(10) 0.0204(9) 0.0019(8) 0.0020(8) 0.0013(8) C2B 0.0236(10) 0.0210(9) 0.0153(9) 0.0027(7) 0.0007(8) -0.0012(8) C3B 0.0234(10) 0.0194(9) 0.0193(9) -0.0003(7) 0.0016(8) -0.0024(8) C4B 0.0232(10) 0.0209(9) 0.0196(10) 0.0014(8) -0.0008(8) 0.0014(8) C5B 0.0221(10) 0.0215(10) 0.0194(10) -0.0007(8) -0.0008(8) 0.0011(8) C6B 0.0293(11) 0.0178(9) 0.0188(10) -0.0009(7) 0.0001(8) -0.0009(8) C7B 0.0278(10) 0.0186(9) 0.0163(9) 0.0011(7) -0.0001(8) 0.0031(8) C8B 0.0435(13) 0.0288(11) 0.0323(12) -0.0039(9) 0.0103(10) 0.0099(10) C9B 0.0360(13) 0.0317(12) 0.0380(13) -0.0001(10) 0.0051(10) 0.0119(10) C10B 0.0525(15) 0.0211(11) 0.0388(13) 0.0053(9) 0.0147(11) -0.0064(10) C11B 0.0548(16) 0.0297(12) 0.0484(15) -0.0061(11) 0.0134(13) -0.0162(11) C12B 0.0240(10) 0.0249(11) 0.0194(10) 0.0004(8) 0.0012(8) -0.0020(8) C13B 0.0231(10) 0.0237(10) 0.0188(9) -0.0022(8) -0.0018(8) -0.0022(8) C14B 0.0273(11) 0.0299(11) 0.0177(10) -0.0036(8) 0.0002(8) -0.0017(9) C15B 0.0277(11) 0.0453(13) 0.0206(10) -0.0090(9) 0.0009(9) 0.0082(10) C16B 0.0388(13) 0.0404(13) 0.0217(11) -0.0027(9) -0.0037(10) 0.0176(11) C17B 0.0441(14) 0.0303(12) 0.0245(11) 0.0051(9) -0.0011(10) 0.0037(10) C18B 0.0280(11) 0.0295(11) 0.0259(11) 0.0003(9) -0.0002(9) -0.0027(9) C19B 0.0256(11) 0.0219(10) 0.0233(10) -0.0029(8) -0.0031(8) 0.0009(8) C20B 0.0292(11) 0.0269(11) 0.0312(12) -0.0033(9) -0.0062(9) 0.0034(9) C21B 0.0239(10) 0.0250(10) 0.0219(10) -0.0015(8) -0.0047(8) 0.0064(8) C22B 0.0180(10) 0.0339(12) 0.0318(11) -0.0015(9) 0.0022(9) 0.0049(9) C23B 0.0264(11) 0.0375(12) 0.0243(11) -0.0054(9) 0.0055(9) 0.0105(9) C24B 0.0269(11) 0.0261(10) 0.0209(10) -0.0060(8) -0.0027(8) 0.0042(9) C25B 0.0207(10) 0.0282(10) 0.0216(10) 0.0037(8) 0.0003(8) 0.0040(8) C26B 0.0294(11) 0.0268(10) 0.0142(9) 0.0013(8) 0.0025(8) 0.0102(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1A C3A 1.7095(19) . ? S1A C1A 1.7367(19) . ? S2A C4A 1.7143(19) . ? S2A C19A 1.7405(19) . ? F1A C14A 1.340(2) . ? F2A C15A 1.334(3) . ? F3A C16A 1.336(2) . ? F4A C17A 1.342(3) . ? F5A C18A 1.334(2) . ? F6A C22A 1.340(2) . ? F7A C23A 1.340(2) . ? F8A C24A 1.331(2) . ? F9A C25A 1.330(2) . ? F10A C26A 1.333(2) . ? O1A C12A 1.212(2) . ? O2A C20A 1.216(2) . ? O3A C7A 1.409(2) . ? O3A C8A 1.438(2) . ? O4A C7A 1.417(2) . ? O4A C9A 1.439(2) . ? O5A C6A 1.407(2) . ? O5A C10A 1.434(3) . ? O6A C6A 1.417(2) . ? O6A C11A 1.438(2) . ? N1A C1A 1.309(2) . ? N1A C2A 1.360(2) . ? N2A C19A 1.305(2) . ? N2A C5A 1.358(2) . ? C1A C12A 1.473(3) . ? C2A C3A 1.375(3) . ? C2A C7A 1.520(3) . ? C3A C4A 1.442(3) . ? C4A C5A 1.372(3) . ? C5A C6A 1.512(3) . ? C6A C7A 1.564(3) . ? C8A C9A 1.501(3) . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C9A H9A1 0.9900 . ? C9A H9A2 0.9900 . ? C10A C11A 1.488(4) . ? C10A H10A 0.9900 . ? C10A H10B 0.9900 . ? C11A H11A 0.9900 . ? C11A H11B 0.9900 . ? C12A C13A 1.497(3) . ? C13A C14A 1.384(3) . ? C13A C18A 1.386(3) . ? C14A C15A 1.372(3) . ? C15A C16A 1.376(3) . ? C16A C17A 1.372(4) . ? C17A C18A 1.379(3) . ? C19A C20A 1.472(3) . ? C20A C21A 1.508(3) . ? C21A C22A 1.388(3) . ? C21A C26A 1.388(3) . ? C22A C23A 1.380(3) . ? C23A C24A 1.374(3) . ? C24A C25A 1.377(3) . ? C25A C26A 1.381(3) . ? S1B C3B 1.7167(19) . ? S1B C1B 1.7364(19) . ? S2B C4B 1.7111(19) . ? S2B C19B 1.739(2) . ? F1B C14B 1.343(2) . ? F2B C15B 1.334(3) . ? F3B C16B 1.336(2) . ? F4B C17B 1.343(3) . ? F5B C18B 1.333(3) . ? F6B C22B 1.337(2) . ? F7B C23B 1.339(2) . ? F8B C24B 1.330(2) . ? F9B C25B 1.331(2) . ? F10B C26B 1.336(2) . ? O1B C12B 1.208(2) . ? O2B C20B 1.211(3) . ? O3B C7B 1.421(2) . ? O3B C8B 1.443(2) . ? O4B C7B 1.397(2) . ? O4B C9B 1.433(3) . ? O5B C6B 1.425(2) . ? O5B C10B 1.441(2) . ? O6B C6B 1.394(2) . ? O6B C11B 1.431(3) . ? N1B C1B 1.309(2) . ? N1B C2B 1.353(2) . ? N2B C19B 1.308(3) . ? N2B C5B 1.355(2) . ? C1B C12B 1.474(3) . ? C2B C3B 1.372(3) . ? C2B C7B 1.514(3) . ? C3B C4B 1.446(3) . ? C4B C5B 1.378(3) . ? C5B C6B 1.515(3) . ? C6B C7B 1.546(3) . ? C8B C9B 1.513(3) . ? C8B H8B1 0.9900 . ? C8B H8B2 0.9900 . ? C9B H9B1 0.9900 . ? C9B H9B2 0.9900 . ? C10B C11B 1.506(3) . ? C10B H10C 0.9900 . ? C10B H10D 0.9900 . ? C11B H11C 0.9900 . ? C11B H11D 0.9900 . ? C12B C13B 1.510(3) . ? C13B C14B 1.381(3) . ? C13B C18B 1.386(3) . ? C14B C15B 1.384(3) . ? C15B C16B 1.377(3) . ? C16B C17B 1.368(4) . ? C17B C18B 1.385(3) . ? C19B C20B 1.473(3) . ? C20B C21B 1.504(3) . ? C21B C26B 1.382(3) . ? C21B C22B 1.387(3) . ? C22B C23B 1.376(3) . ? C23B C24B 1.372(3) . ? C24B C25B 1.378(3) . ? C25B C26B 1.375(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 C3A S1A C1A 88.05(9) . . ? C4A S2A C19A 88.04(9) . . ? C7A O3A C8A 107.01(14) . . ? C7A O4A C9A 106.55(14) . . ? C6A O5A C10A 106.82(16) . . ? C6A O6A C11A 106.64(15) . . ? C1A N1A C2A 109.76(16) . . ? C19A N2A C5A 110.15(16) . . ? N1A C1A C12A 126.00(17) . . ? N1A C1A S1A 115.96(14) . . ? C12A C1A S1A 118.01(14) . . ? N1A C2A C3A 115.52(16) . . ? N1A C2A C7A 122.71(16) . . ? C3A C2A C7A 121.32(16) . . ? C2A C3A C4A 120.64(17) . . ? C2A C3A S1A 110.70(14) . . ? C4A C3A S1A 128.65(14) . . ? C5A C4A C3A 120.50(17) . . ? C5A C4A S2A 110.51(14) . . ? C3A C4A S2A 128.88(14) . . ? N2A C5A C4A 115.60(17) . . ? N2A C5A C6A 121.73(16) . . ? C4A C5A C6A 122.23(17) . . ? O5A C6A O6A 108.16(15) . . ? O5A C6A C5A 111.47(16) . . ? O6A C6A C5A 106.94(15) . . ? O5A C6A C7A 108.18(15) . . ? O6A C6A C7A 110.05(15) . . ? C5A C6A C7A 111.97(15) . . ? O3A C7A O4A 108.20(14) . . ? O3A C7A C2A 112.43(15) . . ? O4A C7A C2A 106.32(15) . . ? O3A C7A C6A 108.39(15) . . ? O4A C7A C6A 109.78(15) . . ? C2A C7A C6A 111.65(15) . . ? O3A C8A C9A 102.80(15) . . ? O3A C8A H8A1 111.2 . . ? C9A C8A H8A1 111.2 . . ? O3A C8A H8A2 111.2 . . ? C9A C8A H8A2 111.2 . . ? H8A1 C8A H8A2 109.1 . . ? O4A C9A C8A 101.73(15) . . ? O4A C9A H9A1 111.4 . . ? C8A C9A H9A1 111.4 . . ? O4A C9A H9A2 111.4 . . ? C8A C9A H9A2 111.4 . . ? H9A1 C9A H9A2 109.3 . . ? O5A C10A C11A 102.72(17) . . ? O5A C10A H10A 111.2 . . ? C11A C10A H10A 111.2 . . ? O5A C10A H10B 111.2 . . ? C11A C10A H10B 111.2 . . ? H10A C10A H10B 109.1 . . ? O6A C11A C10A 102.64(17) . . ? O6A C11A H11A 111.2 . . ? C10A C11A H11A 111.2 . . ? O6A C11A H11B 111.2 . . ? C10A C11A H11B 111.2 . . ? H11A C11A H11B 109.2 . . ? O1A C12A C1A 120.93(18) . . ? O1A C12A C13A 121.50(17) . . ? C1A C12A C13A 117.56(16) . . ? C14A C13A C18A 117.32(18) . . ? C14A C13A C12A 119.66(18) . . ? C18A C13A C12A 123.02(18) . . ? F1A C14A C15A 118.01(19) . . ? F1A C14A C13A 120.05(18) . . ? C15A C14A C13A 121.9(2) . . ? F2A C15A C14A 120.0(2) . . ? F2A C15A C16A 120.6(2) . . ? C14A C15A C16A 119.4(2) . . ? F3A C16A C17A 120.1(2) . . ? F3A C16A C15A 119.5(2) . . ? C17A C16A C15A 120.4(2) . . ? F4A C17A C16A 120.2(2) . . ? F4A C17A C18A 120.4(2) . . ? C16A C17A C18A 119.5(2) . . ? F5A C18A C17A 118.34(19) . . ? F5A C18A C13A 120.09(18) . . ? C17A C18A C13A 121.5(2) . . ? N2A C19A C20A 125.77(17) . . ? N2A C19A S2A 115.66(14) . . ? C20A C19A S2A 118.54(14) . . ? O2A C20A C19A 121.27(18) . . ? O2A C20A C21A 121.82(18) . . ? C19A C20A C21A 116.90(17) . . ? C22A C21A C26A 117.36(18) . . ? C22A C21A C20A 122.79(19) . . ? C26A C21A C20A 119.80(18) . . ? F6A C22A C23A 117.72(18) . . ? F6A C22A C21A 120.74(18) . . ? C23A C22A C21A 121.46(19) . . ? F7A C23A C24A 119.85(18) . . ? F7A C23A C22A 120.38(19) . . ? C24A C23A C22A 119.76(19) . . ? F8A C24A C23A 119.69(19) . . ? F8A C24A C25A 119.97(19) . . ? C23A C24A C25A 120.34(18) . . ? F9A C25A C24A 120.16(17) . . ? F9A C25A C26A 120.55(18) . . ? C24A C25A C26A 119.29(19) . . ? F10A C26A C25A 117.88(18) . . ? F10A C26A C21A 120.35(17) . . ? C25A C26A C21A 121.77(18) . . ? C3B S1B C1B 88.38(9) . . ? C4B S2B C19B 88.30(9) . . ? C7B O3B C8B 107.31(15) . . ? C7B O4B C9B 106.84(15) . . ? C6B O5B C10B 107.05(15) . . ? C6B O6B C11B 107.06(16) . . ? C1B N1B C2B 110.20(16) . . ? C19B N2B C5B 109.86(16) . . ? N1B C1B C12B 122.67(17) . . ? N1B C1B S1B 115.39(14) . . ? C12B C1B S1B 121.93(14) . . ? N1B C2B C3B 116.01(17) . . ? N1B C2B C7B 121.92(17) . . ? C3B C2B C7B 121.98(17) . . ? C2B C3B C4B 119.72(17) . . ? C2B C3B S1B 110.01(14) . . ? C4B C3B S1B 130.26(15) . . ? C5B C4B C3B 119.97(17) . . ? C5B C4B S2B 110.13(14) . . ? C3B C4B S2B 129.66(15) . . ? N2B C5B C4B 115.98(17) . . ? N2B C5B C6B 123.35(17) . . ? C4B C5B C6B 120.58(17) . . ? O6B C6B O5B 108.55(15) . . ? O6B C6B C5B 113.09(15) . . ? O5B C6B C5B 106.09(16) . . ? O6B C6B C7B 108.45(16) . . ? O5B C6B C7B 110.44(15) . . ? C5B C6B C7B 110.20(16) . . ? O4B C7B O3B 108.47(15) . . ? O4B C7B C2B 112.19(15) . . ? O3B C7B C2B 106.63(15) . . ? O4B C7B C6B 108.84(16) . . ? O3B C7B C6B 110.35(15) . . ? C2B C7B C6B 110.33(16) . . ? O3B C8B C9B 101.80(16) . . ? O3B C8B H8B1 111.4 . . ? C9B C8B H8B1 111.4 . . ? O3B C8B H8B2 111.4 . . ? C9B C8B H8B2 111.4 . . ? H8B1 C8B H8B2 109.3 . . ? O4B C9B C8B 102.63(17) . . ? O4B C9B H9B1 111.2 . . ? C8B C9B H9B1 111.2 . . ? O4B C9B H9B2 111.2 . . ? C8B C9B H9B2 111.2 . . ? H9B1 C9B H9B2 109.2 . . ? O5B C10B C11B 102.01(17) . . ? O5B C10B H10C 111.4 . . ? C11B C10B H10C 111.4 . . ? O5B C10B H10D 111.4 . . ? C11B C10B H10D 111.4 . . ? H10C C10B H10D 109.2 . . ? O6B C11B C10B 103.21(18) . . ? O6B C11B H11C 111.1 . . ? C10B C11B H11C 111.1 . . ? O6B C11B H11D 111.1 . . ? C10B C11B H11D 111.1 . . ? H11C C11B H11D 109.1 . . ? O1B C12B C1B 122.97(18) . . ? O1B C12B C13B 122.30(18) . . ? C1B C12B C13B 114.69(16) . . ? C14B C13B C18B 117.24(19) . . ? C14B C13B C12B 120.77(18) . . ? C18B C13B C12B 121.99(19) . . ? F1B C14B C13B 120.22(18) . . ? F1B C14B C15B 117.75(19) . . ? C13B C14B C15B 122.0(2) . . ? F2B C15B C16B 120.5(2) . . ? F2B C15B C14B 120.3(2) . . ? C16B C15B C14B 119.1(2) . . ? F3B C16B C17B 119.9(2) . . ? F3B C16B C15B 119.7(2) . . ? C17B C16B C15B 120.4(2) . . ? F4B C17B C16B 120.3(2) . . ? F4B C17B C18B 120.1(2) . . ? C16B C17B C18B 119.6(2) . . ? F5B C18B C17B 118.1(2) . . ? F5B C18B C13B 120.29(19) . . ? C17B C18B C13B 121.6(2) . . ? N2B C19B C20B 124.18(18) . . ? N2B C19B S2B 115.73(15) . . ? C20B C19B S2B 120.03(15) . . ? O2B C20B C19B 121.06(19) . . ? O2B C20B C21B 121.17(19) . . ? C19B C20B C21B 117.75(18) . . ? C26B C21B C22B 117.19(18) . . ? C26B C21B C20B 120.17(19) . . ? C22B C21B C20B 122.6(2) . . ? F6B C22B C23B 118.18(19) . . ? F6B C22B C21B 120.38(19) . . ? C23B C22B C21B 121.3(2) . . ? F7B C23B C24B 119.56(19) . . ? F7B C23B C22B 120.6(2) . . ? C24B C23B C22B 119.85(19) . . ? F8B C24B C23B 120.02(19) . . ? F8B C24B C25B 119.81(19) . . ? C23B C24B C25B 120.17(19) . . ? F9B C25B C26B 121.12(18) . . ? F9B C25B C24B 119.86(18) . . ? C26B C25B C24B 119.02(19) . . ? F10B C26B C25B 118.21(19) . . ? F10B C26B C21B 119.62(18) . . ? C25B C26B C21B 122.18(19) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.470 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.051 data_16c _database_code_depnum_ccdc_archive 'CCDC 914096' #TrackingRef '16c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Bis-(4-trifluoromethylbenzoyl)-benzo[1,2-d:4,3-d']bis(thiazole)-4,5-bis-(1,3-dioxolane) ; _chemical_name_common ; 2,7-Bis-(4-trifluoromethylbenzoyl)-benzo[1,2-d:4,3-d']bis(thiazole)-4,5-bis-(1,3-dioxolane) ; _chemical_melting_point ? _chemical_formula_moiety 'C28 H16 F6 N2 O6 S2' _chemical_formula_sum 'C28 H16 F6 N2 O6 S2' _chemical_formula_weight 654.55 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' N N 0.0061 0.0033 '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 _symmetry_space_group_name_Hall -P2ybc 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 10.3282(9) _cell_length_b 7.4175(7) _cell_length_c 34.636(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.423(2) _cell_angle_gamma 90.00 _cell_volume 2645.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9882 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 30.60 _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.293 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5951 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24544 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5206 _reflns_number_gt 4740 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0369P)^2^+1.7020P] 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 5206 _refine_ls_number_parameters 429 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0817 _refine_ls_wR_factor_gt 0.0790 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.35180(3) 0.04239(5) 0.288678(11) 0.01833(10) Uani 1 1 d . . . S2 S 0.49407(4) 0.05263(5) 0.195124(11) 0.01942(10) Uani 1 1 d . B . F1 F 0.33982(13) -0.42554(15) 0.51565(3) 0.0450(3) Uani 1 1 d . . . F2 F 0.32697(11) -0.17308(17) 0.54566(3) 0.0426(3) Uani 1 1 d . . . F3 F 0.51189(10) -0.27411(15) 0.53192(3) 0.0359(3) Uani 1 1 d . . . F4 F 1.2205(9) 0.167(2) 0.0785(3) 0.076(3) Uani 0.50 1 d P A 1 F5 F 1.1162(11) 0.4039(11) 0.0608(3) 0.065(3) Uani 0.50 1 d P A 1 F6 F 1.1166(6) 0.1726(6) 0.02339(16) 0.0302(9) Uani 0.50 1 d P A 1 F4A F 1.2214(9) 0.199(2) 0.0791(3) 0.077(3) Uani 0.50 1 d P A 2 F5A F 1.1004(12) 0.4069(14) 0.0548(3) 0.084(3) Uani 0.50 1 d P A 2 F6A F 1.1060(9) 0.1624(12) 0.0259(3) 0.094(3) Uani 0.50 1 d P A 2 O1 O 0.19270(10) 0.09842(16) 0.35516(3) 0.0243(2) Uani 1 1 d . . . O2 O 0.55711(12) -0.02933(17) 0.11541(3) 0.0293(3) Uani 1 1 d . . . O3 O 0.75575(10) 0.28973(14) 0.30585(3) 0.0193(2) Uani 1 1 d . . . O4 O 0.80519(10) 0.04863(14) 0.34554(3) 0.0198(2) Uani 1 1 d . . . O5 O 0.91448(9) 0.05025(14) 0.27140(3) 0.0176(2) Uani 1 1 d . B . O6 O 0.78608(10) -0.18812(14) 0.28655(3) 0.0179(2) Uani 1 1 d . B . N1 N 0.52943(12) 0.06811(16) 0.34539(4) 0.0172(3) Uani 1 1 d . B . N2 N 0.74433(12) 0.01860(17) 0.20452(4) 0.0175(3) Uani 1 1 d . B . C1 C 0.40338(14) 0.05324(19) 0.33766(4) 0.0174(3) Uani 1 1 d . . . C2 C 0.58977(14) 0.07143(18) 0.31206(4) 0.0156(3) Uani 1 1 d . . . C3 C 0.51089(14) 0.05690(19) 0.27825(4) 0.0168(3) Uani 1 1 d . B . C4 C 0.56706(14) 0.04819(19) 0.24128(4) 0.0175(3) Uani 1 1 d . . . C5 C 0.69944(14) 0.02860(19) 0.24020(4) 0.0168(3) Uani 1 1 d . B . C6 C 0.78627(13) -0.00160(19) 0.27691(4) 0.0158(3) Uani 1 1 d . . . C7 C 0.73485(14) 0.1016(2) 0.31126(4) 0.0165(3) Uani 1 1 d . B . C8 C 0.83766(19) 0.2099(2) 0.36702(5) 0.0319(4) Uani 1 1 d . B . H8A H 0.9205 0.1960 0.3831 0.038 Uiso 0.867(7) 1 calc PR B 1 H8B H 0.7682 0.2433 0.3838 0.038 Uiso 0.867(7) 1 calc PR B 1 H8C H 0.9332 0.2248 0.3698 0.038 Uiso 0.133(7) 1 d PR B 2 H8D H 0.8064 0.2001 0.3932 0.038 Uiso 0.133(7) 1 d PR B 2 C9 C 0.8498(2) 0.3470(3) 0.33556(6) 0.0295(7) Uani 0.867(7) 1 d P B 1 H9A H 0.8301 0.4697 0.3447 0.035 Uiso 0.867(7) 1 calc PR B 1 H9B H 0.9382 0.3461 0.3264 0.035 Uiso 0.867(7) 1 calc PR B 1 C9A C 0.7794(13) 0.3644(15) 0.3475(3) 0.016(3) Uiso 0.133(7) 1 d P B 2 H9A1 H 0.8392 0.4690 0.3486 0.019 Uiso 0.133(7) 1 calc PR B 2 H9A2 H 0.6971 0.3991 0.3584 0.019 Uiso 0.133(7) 1 calc PR B 2 C10 C 0.99646(14) -0.1043(2) 0.27871(5) 0.0221(3) Uani 1 1 d . . . H10A H 1.0368 -0.1039 0.3056 0.027 Uiso 1 1 calc R B . H10B H 1.0656 -0.1094 0.2605 0.027 Uiso 1 1 calc R . . C11 C 0.90281(14) -0.2588(2) 0.27221(5) 0.0196(3) Uani 1 1 d . B . H11A H 0.8894 -0.2898 0.2444 0.023 Uiso 1 1 calc R . . H11B H 0.9336 -0.3670 0.2869 0.023 Uiso 1 1 calc R . . C12 C 0.30308(14) 0.05136(19) 0.36622(4) 0.0182(3) Uani 1 1 d . . . C13 C 0.33608(14) -0.0147(2) 0.40639(4) 0.0181(3) Uani 1 1 d . . . C14 C 0.44817(15) -0.1136(2) 0.41699(5) 0.0206(3) Uani 1 1 d . . . H14 H 0.5125 -0.1290 0.3991 0.025 Uiso 1 1 calc R . . C15 C 0.46580(15) -0.1892(2) 0.45358(5) 0.0218(3) Uani 1 1 d . . . H15 H 0.5412 -0.2589 0.4606 0.026 Uiso 1 1 calc R . . C16 C 0.37322(15) -0.1631(2) 0.47997(4) 0.0217(3) Uani 1 1 d . . . C17 C 0.26260(16) -0.0602(2) 0.47016(5) 0.0233(3) Uani 1 1 d . . . H17 H 0.2006 -0.0400 0.4886 0.028 Uiso 1 1 calc R . . C18 C 0.24384(15) 0.0123(2) 0.43341(5) 0.0209(3) Uani 1 1 d . . . H18 H 0.1679 0.0808 0.4264 0.025 Uiso 1 1 calc R . . C19 C 0.38804(16) -0.2577(2) 0.51834(5) 0.0268(3) Uani 1 1 d . . . C20 C 0.64676(14) 0.0294(2) 0.17788(4) 0.0184(3) Uani 1 1 d . . . C21 C 0.65479(15) 0.0129(2) 0.13531(4) 0.0205(3) Uani 1 1 d . B . C22 C 0.77918(15) 0.05405(19) 0.11780(4) 0.0188(3) Uani 1 1 d . . . C23 C 0.87749(15) 0.1552(2) 0.13719(4) 0.0201(3) Uani 1 1 d . B . H23 H 0.8707 0.1874 0.1635 0.024 Uiso 1 1 calc R . . C24 C 0.98500(15) 0.2095(2) 0.11861(4) 0.0211(3) Uani 1 1 d . . . H24 H 1.0507 0.2809 0.1318 0.025 Uiso 1 1 calc R B . C25 C 0.99538(15) 0.1583(2) 0.08046(5) 0.0236(3) Uani 1 1 d . A . C26 C 0.89964(17) 0.0534(2) 0.06100(5) 0.0276(4) Uani 1 1 d . . . H26 H 0.9087 0.0163 0.0351 0.033 Uiso 1 1 calc R B . C27 C 0.79120(17) 0.0031(2) 0.07945(5) 0.0244(3) Uani 1 1 d . B . H27 H 0.7248 -0.0663 0.0660 0.029 Uiso 1 1 calc R . . C28 C 1.10887(19) 0.2273(3) 0.06036(5) 0.0363(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01212(17) 0.02292(19) 0.01976(19) 0.00250(14) 0.00001(14) -0.00034(13) S2 0.01611(18) 0.02370(19) 0.01782(19) 0.00270(14) -0.00270(14) -0.00326(14) F1 0.0626(8) 0.0351(6) 0.0355(6) 0.0124(5) -0.0075(5) -0.0199(5) F2 0.0490(7) 0.0564(7) 0.0237(5) 0.0054(5) 0.0124(5) 0.0116(6) F3 0.0325(5) 0.0477(6) 0.0265(5) 0.0089(5) -0.0036(4) 0.0011(5) F4 0.024(4) 0.138(6) 0.069(5) 0.019(4) 0.019(3) 0.019(4) F5 0.097(5) 0.043(4) 0.063(3) -0.032(3) 0.060(3) -0.048(4) F6 0.036(2) 0.0393(17) 0.0171(19) -0.0099(14) 0.0171(15) -0.0072(15) F4A 0.033(4) 0.162(8) 0.037(3) 0.004(3) 0.000(3) -0.038(4) F5A 0.088(4) 0.058(5) 0.114(6) 0.023(4) 0.069(4) 0.004(3) F6A 0.076(4) 0.158(6) 0.053(4) -0.039(4) 0.043(3) -0.052(4) O1 0.0155(5) 0.0303(6) 0.0272(6) 0.0027(5) 0.0019(4) 0.0028(4) O2 0.0289(6) 0.0367(7) 0.0214(6) 0.0010(5) -0.0048(5) -0.0132(5) O3 0.0172(5) 0.0173(5) 0.0231(5) -0.0020(4) -0.0003(4) -0.0028(4) O4 0.0170(5) 0.0260(6) 0.0159(5) 0.0009(4) -0.0024(4) -0.0005(4) O5 0.0117(5) 0.0198(5) 0.0216(5) 0.0036(4) 0.0018(4) 0.0007(4) O6 0.0163(5) 0.0170(5) 0.0209(5) 0.0032(4) 0.0042(4) 0.0013(4) N1 0.0155(6) 0.0157(6) 0.0204(6) -0.0004(5) 0.0015(5) 0.0001(5) N2 0.0186(6) 0.0172(6) 0.0167(6) 0.0011(5) 0.0006(5) -0.0015(5) C1 0.0180(7) 0.0165(7) 0.0178(7) 0.0008(5) 0.0009(6) 0.0009(5) C2 0.0150(7) 0.0134(6) 0.0184(7) -0.0002(5) 0.0020(5) 0.0000(5) C3 0.0132(7) 0.0158(7) 0.0212(7) 0.0017(6) 0.0013(6) -0.0001(5) C4 0.0168(7) 0.0172(7) 0.0180(7) 0.0018(6) -0.0010(6) -0.0019(5) C5 0.0168(7) 0.0160(7) 0.0176(7) 0.0006(5) 0.0012(6) -0.0008(5) C6 0.0120(6) 0.0172(7) 0.0181(7) 0.0020(6) 0.0010(5) -0.0008(5) C7 0.0138(7) 0.0181(7) 0.0172(7) 0.0014(6) -0.0009(5) -0.0007(5) C8 0.0400(10) 0.0347(10) 0.0201(8) -0.0068(7) -0.0022(7) -0.0079(8) C9 0.0284(13) 0.0310(11) 0.0284(11) -0.0058(8) -0.0029(9) -0.0117(8) C10 0.0157(7) 0.0221(8) 0.0280(8) 0.0040(6) -0.0020(6) 0.0028(6) C11 0.0142(7) 0.0207(7) 0.0237(8) 0.0011(6) 0.0003(6) 0.0041(6) C12 0.0161(7) 0.0162(7) 0.0223(8) -0.0013(6) 0.0018(6) -0.0012(5) C13 0.0172(7) 0.0168(7) 0.0204(7) -0.0013(6) 0.0017(6) -0.0027(6) C14 0.0179(7) 0.0215(7) 0.0228(8) -0.0009(6) 0.0038(6) -0.0003(6) C15 0.0185(7) 0.0217(8) 0.0251(8) 0.0012(6) 0.0008(6) 0.0008(6) C16 0.0231(8) 0.0214(7) 0.0204(8) -0.0002(6) 0.0012(6) -0.0052(6) C17 0.0223(8) 0.0256(8) 0.0228(8) -0.0027(6) 0.0069(6) -0.0017(6) C18 0.0172(7) 0.0202(7) 0.0254(8) -0.0011(6) 0.0028(6) 0.0003(6) C19 0.0280(8) 0.0283(8) 0.0242(8) 0.0016(7) 0.0023(7) -0.0036(7) C20 0.0190(7) 0.0177(7) 0.0184(7) 0.0019(6) 0.0010(6) -0.0024(6) C21 0.0254(8) 0.0171(7) 0.0183(7) 0.0017(6) -0.0024(6) -0.0038(6) C22 0.0227(8) 0.0159(7) 0.0175(7) 0.0024(6) -0.0009(6) 0.0005(6) C23 0.0236(8) 0.0207(7) 0.0158(7) -0.0003(6) -0.0006(6) 0.0003(6) C24 0.0210(7) 0.0220(8) 0.0201(7) 0.0001(6) -0.0003(6) 0.0012(6) C25 0.0242(8) 0.0252(8) 0.0217(8) 0.0003(6) 0.0040(6) 0.0045(6) C26 0.0353(9) 0.0290(9) 0.0187(8) -0.0055(6) 0.0037(7) 0.0018(7) C27 0.0317(9) 0.0213(8) 0.0196(8) -0.0019(6) -0.0025(6) -0.0020(7) C28 0.0338(10) 0.0499(12) 0.0265(9) -0.0078(8) 0.0110(8) -0.0026(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C3 1.7126(15) . ? S1 C1 1.7403(15) . ? S2 C4 1.7144(15) . ? S2 C20 1.7375(15) . ? F1 C19 1.342(2) . ? F2 C19 1.334(2) . ? F3 C19 1.3339(19) . ? F4 C28 1.345(10) . ? F5 C28 1.312(8) . ? F6 C28 1.351(6) . ? F4A C28 1.303(9) . ? F5A C28 1.348(11) . ? F6A C28 1.285(9) . ? O1 C12 1.2251(18) . ? O2 C21 1.2181(19) . ? O3 C9 1.424(2) . ? O3 C7 1.4269(18) . ? O3 C9A 1.548(11) . ? O4 C7 1.3995(17) . ? O4 C8 1.435(2) . ? O5 C6 1.4060(17) . ? O5 C10 1.4362(18) . ? O6 C6 1.4233(17) . ? O6 C11 1.4379(17) . ? N1 C1 1.3133(19) . ? N1 C2 1.3538(19) . ? N2 C20 1.3153(19) . ? N2 C5 1.3549(19) . ? C1 C12 1.487(2) . ? C2 C3 1.378(2) . ? C2 C7 1.5173(19) . ? C3 C4 1.448(2) . ? C4 C5 1.378(2) . ? C5 C6 1.515(2) . ? C6 C7 1.543(2) . ? C8 C9A 1.438(11) . ? C8 C9 1.503(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 H8C 0.9900 . ? C8 H8D 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9A H9A1 0.9900 . ? C9A H9A2 0.9900 . ? C10 C11 1.505(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.490(2) . ? C13 C14 1.396(2) . ? C13 C18 1.400(2) . ? C14 C15 1.385(2) . ? C14 H14 0.9500 . ? C15 C16 1.386(2) . ? C15 H15 0.9500 . ? C16 C17 1.394(2) . ? C16 C19 1.500(2) . ? C17 C18 1.381(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C20 C21 1.488(2) . ? C21 C22 1.494(2) . ? C22 C23 1.393(2) . ? C22 C27 1.396(2) . ? C23 C24 1.385(2) . ? C23 H23 0.9500 . ? C24 C25 1.387(2) . ? C24 H24 0.9500 . ? C25 C26 1.391(2) . ? C25 C28 1.499(2) . ? C26 C27 1.383(2) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 S1 C1 88.63(7) . . ? C4 S2 C20 88.46(7) . . ? C9 O3 C7 107.36(12) . . ? C9 O3 C9A 33.9(5) . . ? C7 O3 C9A 104.0(4) . . ? C7 O4 C8 106.92(12) . . ? C6 O5 C10 107.84(11) . . ? C6 O6 C11 104.91(10) . . ? C1 N1 C2 109.99(13) . . ? C20 N2 C5 109.81(13) . . ? N1 C1 C12 126.56(14) . . ? N1 C1 S1 115.26(11) . . ? C12 C1 S1 118.14(11) . . ? N1 C2 C3 116.24(13) . . ? N1 C2 C7 122.57(13) . . ? C3 C2 C7 121.07(13) . . ? C2 C3 C4 120.27(13) . . ? C2 C3 S1 109.86(11) . . ? C4 C3 S1 129.81(11) . . ? C5 C4 C3 119.66(13) . . ? C5 C4 S2 110.03(11) . . ? C3 C4 S2 130.29(11) . . ? N2 C5 C4 116.13(13) . . ? N2 C5 C6 122.37(13) . . ? C4 C5 C6 121.13(13) . . ? O5 C6 O6 108.42(11) . . ? O5 C6 C5 110.39(11) . . ? O6 C6 C5 109.21(11) . . ? O5 C6 C7 110.66(11) . . ? O6 C6 C7 107.13(11) . . ? C5 C6 C7 110.93(12) . . ? O4 C7 O3 108.18(11) . . ? O4 C7 C2 113.08(12) . . ? O3 C7 C2 107.82(11) . . ? O4 C7 C6 109.15(11) . . ? O3 C7 C6 108.61(11) . . ? C2 C7 C6 109.88(12) . . ? O4 C8 C9A 110.4(4) . . ? O4 C8 C9 102.57(13) . . ? C9A C8 C9 34.5(5) . . ? O4 C8 H8A 111.3 . . ? C9A C8 H8A 131.3 . . ? C9 C8 H8A 111.3 . . ? O4 C8 H8B 111.3 . . ? C9A C8 H8B 77.4 . . ? C9 C8 H8B 111.3 . . ? H8A C8 H8B 109.2 . . ? O4 C8 H8C 109.6 . . ? C9A C8 H8C 109.6 . . ? C9 C8 H8C 81.8 . . ? H8A C8 H8C 31.3 . . ? H8B C8 H8C 132.6 . . ? O4 C8 H8D 109.6 . . ? C9A C8 H8D 109.6 . . ? C9 C8 H8D 140.0 . . ? H8A C8 H8D 78.7 . . ? H8B C8 H8D 34.5 . . ? H8C C8 H8D 108.1 . . ? O3 C9 C8 103.40(14) . . ? O3 C9 H9A 111.1 . . ? C8 C9 H9A 111.1 . . ? O3 C9 H9B 111.1 . . ? C8 C9 H9B 111.1 . . ? H9A C9 H9B 109.0 . . ? C8 C9A O3 100.5(7) . . ? C8 C9A H9A1 111.7 . . ? O3 C9A H9A1 111.7 . . ? C8 C9A H9A2 111.7 . . ? O3 C9A H9A2 111.7 . . ? H9A1 C9A H9A2 109.4 . . ? O5 C10 C11 102.60(11) . . ? O5 C10 H10A 111.2 . . ? C11 C10 H10A 111.2 . . ? O5 C10 H10B 111.2 . . ? C11 C10 H10B 111.2 . . ? H10A C10 H10B 109.2 . . ? O6 C11 C10 102.53(12) . . ? O6 C11 H11A 111.3 . . ? C10 C11 H11A 111.3 . . ? O6 C11 H11B 111.3 . . ? C10 C11 H11B 111.3 . . ? H11A C11 H11B 109.2 . . ? O1 C12 C1 117.95(14) . . ? O1 C12 C13 121.73(14) . . ? C1 C12 C13 120.25(13) . . ? C14 C13 C18 119.50(14) . . ? C14 C13 C12 122.96(13) . . ? C18 C13 C12 117.32(13) . . ? C15 C14 C13 120.11(14) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 119.86(14) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C15 C16 C17 120.63(15) . . ? C15 C16 C19 119.36(15) . . ? C17 C16 C19 119.86(14) . . ? C18 C17 C16 119.46(15) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C13 120.39(14) . . ? C17 C18 H18 119.8 . . ? C13 C18 H18 119.8 . . ? F2 C19 F3 106.61(13) . . ? F2 C19 F1 107.01(14) . . ? F3 C19 F1 106.28(14) . . ? F2 C19 C16 112.77(14) . . ? F3 C19 C16 112.63(13) . . ? F1 C19 C16 111.13(14) . . ? N2 C20 C21 126.29(14) . . ? N2 C20 S2 115.56(11) . . ? C21 C20 S2 118.04(11) . . ? O2 C21 C20 118.34(14) . . ? O2 C21 C22 121.57(14) . . ? C20 C21 C22 120.06(13) . . ? C23 C22 C27 119.33(15) . . ? C23 C22 C21 122.14(14) . . ? C27 C22 C21 118.26(14) . . ? C24 C23 C22 120.88(14) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C25 119.12(15) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? C24 C25 C26 120.70(15) . . ? C24 C25 C28 118.04(15) . . ? C26 C25 C28 121.19(15) . . ? C27 C26 C25 119.86(15) . . ? C27 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? C26 C27 C22 120.08(15) . . ? C26 C27 H27 120.0 . . ? C22 C27 H27 120.0 . . ? F6A C28 F4A 111.0(7) . . ? F6A C28 F5 112.5(6) . . ? F4A C28 F5 96.0(9) . . ? F6A C28 F4 105.4(7) . . ? F4A C28 F4 10.3(13) . . ? F5 C28 F4 106.2(9) . . ? F6A C28 F5A 103.9(7) . . ? F4A C28 F5A 105.9(9) . . ? F5 C28 F5A 10.9(10) . . ? F4 C28 F5A 116.0(9) . . ? F6A C28 F6 6.5(6) . . ? F4A C28 F6 107.9(5) . . ? F5 C28 F6 107.6(5) . . ? F4 C28 F6 103.3(6) . . ? F5A C28 F6 99.7(5) . . ? F6A C28 C25 109.9(4) . . ? F4A C28 C25 114.5(6) . . ? F5 C28 C25 112.4(4) . . ? F4 C28 C25 110.1(6) . . ? F5A C28 C25 111.1(5) . . ? F6 C28 C25 116.3(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.359 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.045 data_16d _database_code_depnum_ccdc_archive 'CCDC 914097' #TrackingRef '16d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Bis-(thiophen-2-oyl)-benzo[1,2-d:4,3-d']bis(thiazole)-4,5-bis-(1,3-dioxolane) ; _chemical_name_common ; 2,7-Bis-(thiophen-2-oyl)-benzo[1,2-d:4,3-d']bis(thiazole)-4,5-bis-(1,3-dioxolane) ; _chemical_melting_point ? _chemical_formula_moiety 'C22 H14 N2 O6 S4' _chemical_formula_sum 'C22 H14 N2 O6 S4' _chemical_formula_weight 530.59 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc 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' '-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 16.860(2) _cell_length_b 15.304(2) _cell_length_c 10.1282(14) _cell_angle_alpha 90.00 _cell_angle_beta 124.484(2) _cell_angle_gamma 90.00 _cell_volume 2154.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9871 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 30.56 _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.487 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9714 _exptl_absorpt_correction_T_max 0.9951 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10066 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2123 _reflns_number_gt 2033 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0481P)^2^+2.2303P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2123 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0846 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 0.05059(3) 0.08473(2) -0.04018(4) 0.01772(14) Uani 1 1 d . . . S2 S 0.18538(10) 0.12052(8) 0.58492(15) 0.0204(2) Uani 0.75 1 d P A 1 C4 C 0.1260(6) 0.2591(4) 0.4168(9) 0.0284(14) Uani 0.75 1 d P A 1 H4 H 0.1017 0.2986 0.3298 0.034 Uiso 0.75 1 calc PR A 1 C4A C 0.1684(13) 0.1444(9) 0.559(2) 0.024(3) Uani 0.25 1 d P B 2 H4A H 0.187(6) 0.075(6) 0.595(11) 0.029 Uiso 0.25 1 d P C 2 S2A S 0.1208(4) 0.2843(3) 0.3971(6) 0.0207(7) Uani 0.25 1 d P D 2 O1 O 0.13934(9) 0.04001(7) 0.29026(13) 0.0292(3) Uani 1 1 d . A 1 O2 O 0.01994(8) 0.40632(7) -0.09062(13) 0.0213(3) Uani 1 1 d . E 1 O3 O 0.13205(8) 0.34963(7) -0.12714(13) 0.0210(2) Uani 1 1 d . E 1 N1 N 0.08281(8) 0.24131(8) 0.07837(14) 0.0157(3) Uani 1 1 d . A 1 C1 C 0.08893(10) 0.15819(9) 0.11531(16) 0.0164(3) Uani 1 1 d . A 1 C2 C 0.12500(11) 0.11933(10) 0.27446(17) 0.0188(3) Uani 1 1 d . A 1 C3 C 0.14038(10) 0.17368(10) 0.40545(17) 0.0177(3) Uani 1 1 d . A 1 C5 C 0.15044(11) 0.28541(11) 0.5723(2) 0.0242(3) Uani 1 1 d . A 1 H5 H 0.1456 0.3430 0.6021 0.029 Uiso 1 1 calc R A 1 C6 C 0.18152(11) 0.21407(11) 0.66911(19) 0.0223(3) Uani 1 1 d . A 1 H6 H 0.1998 0.2167 0.7766 0.027 Uiso 1 1 calc R A 1 C7 C 0.02190(10) 0.17180(9) -0.16450(16) 0.0148(3) Uani 1 1 d . . 1 C8 C 0.04519(10) 0.24908(9) -0.08090(17) 0.0148(3) Uani 1 1 d . A 1 C9 C 0.03950(10) 0.33582(9) -0.15747(16) 0.0162(3) Uani 1 1 d . . 1 C10 C 0.10714(14) 0.45503(12) 0.0066(2) 0.0336(4) Uani 1 1 d . E 1 H10A H 0.1451 0.4335 0.1185 0.040 Uiso 1 1 calc R E 1 H10B H 0.0937 0.5180 0.0061 0.040 Uiso 1 1 calc R E 1 C11 C 0.15899(13) 0.43843(12) -0.0730(2) 0.0313(4) Uani 1 1 d . E 1 H11A H 0.1369 0.4789 -0.1638 0.038 Uiso 1 1 calc R E 1 H11B H 0.2295 0.4442 0.0041 0.038 Uiso 1 1 calc R E 1 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 0.0261(2) 0.0143(2) 0.0119(2) 0.00105(12) 0.01021(17) 0.00084(13) S2 0.0308(5) 0.0188(6) 0.0100(4) 0.0017(4) 0.0105(4) -0.0001(4) C4 0.0257(17) 0.040(4) 0.020(2) 0.007(2) 0.0131(15) 0.001(2) C4A 0.035(8) 0.013(7) 0.029(7) 0.008(5) 0.021(6) -0.002(5) S2A 0.0205(11) 0.031(2) 0.0132(14) -0.0018(13) 0.0110(10) -0.0019(13) O1 0.0449(7) 0.0191(6) 0.0158(5) 0.0035(4) 0.0125(5) 0.0043(5) O2 0.0340(6) 0.0150(5) 0.0174(5) -0.0025(4) 0.0161(5) 0.0013(4) O3 0.0231(5) 0.0220(5) 0.0197(5) -0.0041(4) 0.0133(5) -0.0070(4) N1 0.0176(6) 0.0176(6) 0.0121(6) 0.0005(5) 0.0086(5) 0.0007(5) C1 0.0183(7) 0.0185(7) 0.0118(7) -0.0007(5) 0.0081(6) 0.0009(5) C2 0.0208(7) 0.0199(7) 0.0127(7) 0.0018(6) 0.0076(6) 0.0004(6) C3 0.0189(7) 0.0210(8) 0.0119(7) 0.0016(5) 0.0078(6) -0.0011(6) C5 0.0231(8) 0.0268(8) 0.0254(8) 0.0003(7) 0.0153(7) 0.0017(6) C6 0.0230(7) 0.0309(8) 0.0164(7) -0.0011(6) 0.0132(6) -0.0009(6) C7 0.0176(7) 0.0162(7) 0.0121(7) 0.0013(5) 0.0094(6) 0.0008(5) C8 0.0157(6) 0.0174(7) 0.0124(6) 0.0002(5) 0.0085(5) 0.0006(5) C9 0.0224(7) 0.0155(7) 0.0135(7) -0.0015(5) 0.0119(6) -0.0003(5) C10 0.0417(10) 0.0258(9) 0.0264(9) -0.0118(7) 0.0152(8) -0.0069(7) C11 0.0380(10) 0.0249(9) 0.0267(9) -0.0061(7) 0.0158(8) -0.0150(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 C7 1.7044(14) . ? S1 C1 1.7346(14) . ? S2 C6 1.686(2) . ? S2 C3 1.7263(19) . ? S2 H4A 0.70(10) . ? C4 C3 1.346(6) . ? C4 C5 1.441(9) . ? C4 H4 0.9500 . ? C4A H4A 1.11(10) . ? O1 C2 1.2303(19) . ? O2 C9 1.4085(17) . ? O2 C10 1.431(2) . ? O3 C9 1.4252(18) . ? O3 C11 1.439(2) . ? N1 C1 1.3135(19) . ? N1 C8 1.3638(18) . ? C1 C2 1.4872(19) . ? C2 C3 1.459(2) . ? C5 C6 1.359(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.376(2) . ? C7 C7 1.448(3) 2_554 ? C8 C9 1.5128(19) . ? C9 C9 1.569(3) 2_554 ? C10 C11 1.509(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? 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 C7 S1 C1 88.17(7) . . ? C6 S2 C3 90.72(9) . . ? C6 S2 H4A 141(7) . . ? C3 S2 H4A 125(8) . . ? C3 C4 C5 114.3(4) . . ? C3 C4 H4 122.9 . . ? C5 C4 H4 122.9 . . ? C9 O2 C10 107.52(12) . . ? C9 O3 C11 107.02(12) . . ? C1 N1 C8 109.28(12) . . ? N1 C1 C2 127.88(13) . . ? N1 C1 S1 116.12(10) . . ? C2 C1 S1 116.00(11) . . ? O1 C2 C3 121.57(13) . . ? O1 C2 C1 117.72(13) . . ? C3 C2 C1 120.70(13) . . ? C4 C3 C2 133.1(3) . . ? C4 C3 S2 111.1(3) . . ? C2 C3 S2 115.75(12) . . ? C6 C5 C4 108.6(2) . . ? C6 C5 H5 125.7 . . ? C4 C5 H5 125.7 . . ? C5 C6 S2 115.27(13) . . ? C5 C6 H6 122.4 . . ? S2 C6 H6 122.4 . . ? C8 C7 C7 120.71(8) . 2_554 ? C8 C7 S1 110.77(10) . . ? C7 C7 S1 128.52(5) 2_554 . ? N1 C8 C7 115.63(12) . . ? N1 C8 C9 122.33(12) . . ? C7 C8 C9 121.71(13) . . ? O2 C9 O3 107.97(11) . . ? O2 C9 C8 112.95(11) . . ? O3 C9 C8 106.00(11) . . ? O2 C9 C9 107.63(11) . 2_554 ? O3 C9 C9 110.05(13) . 2_554 ? C8 C9 C9 112.15(9) . 2_554 ? O2 C10 C11 102.98(13) . . ? O2 C10 H10A 111.2 . . ? C11 C10 H10A 111.2 . . ? O2 C10 H10B 111.2 . . ? C11 C10 H10B 111.2 . . ? H10A C10 H10B 109.1 . . ? O3 C11 C10 102.09(13) . . ? O3 C11 H11A 111.4 . . ? C10 C11 H11A 111.4 . . ? O3 C11 H11B 111.4 . . ? C10 C11 H11B 111.4 . . ? H11A C11 H11B 109.2 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.332 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.067 data_q1 _database_code_depnum_ccdc_archive 'CCDC 914098' #TrackingRef '19b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Bis-(5-n-nonyl-thiophen-2-yl)-benzo[1,2-b:6,5-b']dithiophene-4,5-dione ; _chemical_name_common ; 2,7-Bis-(5-n-nonyl-thiophen-2-yl)-benzo[1,2-b:6,5-b']dithiophene-4,5-dione ; _chemical_melting_point ? _chemical_formula_moiety 'C36 H44 O2 S4' _chemical_formula_sum 'C36 H44 O2 S4' _chemical_formula_weight 636.95 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.349(3) _cell_length_b 11.374(5) _cell_length_c 20.588(9) _cell_angle_alpha 76.147(8) _cell_angle_beta 82.786(8) _cell_angle_gamma 75.325(7) _cell_volume 1612.4(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1718 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 30.40 _exptl_crystal_description plates _exptl_crystal_colour black _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.327 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5068 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15160 _diffrn_reflns_av_R_equivalents 0.0936 _diffrn_reflns_av_sigmaI/netI 0.1349 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6315 _reflns_number_gt 3670 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0842P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6315 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1319 _refine_ls_R_factor_gt 0.0690 _refine_ls_wR_factor_ref 0.1801 _refine_ls_wR_factor_gt 0.1520 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _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 -0.25990(15) 0.26274(10) 0.24449(6) 0.0187(3) Uani 1 1 d . . . S2 S 0.10445(15) 0.41821(10) 0.17723(6) 0.0187(3) Uani 1 1 d . . . S3 S 0.41944(16) 0.71242(10) 0.12761(6) 0.0193(3) Uani 1 1 d . . . S4 S -0.79691(16) 0.18709(11) 0.34445(6) 0.0219(3) Uani 1 1 d . . . O1 O -0.5895(4) 0.6533(3) 0.31331(17) 0.0287(8) Uani 1 1 d . . . O2 O -0.3060(5) 0.7747(3) 0.25912(17) 0.0292(8) Uani 1 1 d . . . C1 C -0.4845(6) 0.2766(4) 0.2873(2) 0.0167(10) Uani 1 1 d . . . C2 C -0.5480(6) 0.3935(4) 0.3002(2) 0.0197(10) Uani 1 1 d . . . H2 H -0.6646 0.4191 0.3223 0.024 Uiso 1 1 calc R . . C3 C -0.4214(6) 0.4715(4) 0.2771(2) 0.0173(10) Uani 1 1 d . . . C4 C -0.2561(6) 0.4126(4) 0.2453(2) 0.0164(10) Uani 1 1 d . . . C5 C -0.1069(6) 0.4762(4) 0.2190(2) 0.0154(10) Uani 1 1 d . . . C6 C -0.1172(6) 0.5954(4) 0.2252(2) 0.0177(10) Uani 1 1 d . . . C7 C -0.2888(6) 0.6679(4) 0.2562(2) 0.0203(10) Uani 1 1 d . . . C8 C -0.4491(6) 0.5989(4) 0.2853(2) 0.0205(10) Uani 1 1 d . . . C9 C 0.0438(6) 0.6403(4) 0.1964(2) 0.0196(10) Uani 1 1 d . . . H9 H 0.0579 0.7192 0.1968 0.024 Uiso 1 1 calc R . . C10 C 0.1771(6) 0.5561(4) 0.1678(2) 0.0159(10) Uani 1 1 d . . . C11 C 0.3540(6) 0.5746(4) 0.1321(2) 0.0179(10) Uani 1 1 d . . . C12 C 0.4878(6) 0.4991(4) 0.0978(2) 0.0191(10) Uani 1 1 d . . . H12 H 0.4791 0.4208 0.0943 0.023 Uiso 1 1 calc R . . C13 C 0.6417(6) 0.5542(4) 0.0680(2) 0.0216(11) Uani 1 1 d . . . H13 H 0.7436 0.5145 0.0434 0.026 Uiso 1 1 calc R . . C14 C 0.6255(6) 0.6692(4) 0.0790(2) 0.0168(10) Uani 1 1 d . . . C15 C 0.7487(6) 0.7608(4) 0.0565(2) 0.0196(10) Uani 1 1 d . . . H15A H 0.7785 0.7835 0.0958 0.024 Uiso 1 1 calc R . . H15B H 0.6772 0.8356 0.0288 0.024 Uiso 1 1 calc R . . C16 C 0.9328(6) 0.7153(4) 0.0172(2) 0.0173(10) Uani 1 1 d . . . H16A H 0.9056 0.6929 -0.0226 0.021 Uiso 1 1 calc R . . H16B H 1.0078 0.6417 0.0446 0.021 Uiso 1 1 calc R . . C17 C 1.0440(6) 0.8167(4) -0.0033(2) 0.0197(10) Uani 1 1 d . . . H17A H 1.0694 0.8387 0.0368 0.024 Uiso 1 1 calc R . . H17B H 0.9666 0.8902 -0.0299 0.024 Uiso 1 1 calc R . . C18 C 1.2308(6) 0.7794(4) -0.0435(2) 0.0176(10) Uani 1 1 d . . . H18A H 1.3110 0.7084 -0.0161 0.021 Uiso 1 1 calc R . . H18B H 1.2063 0.7537 -0.0826 0.021 Uiso 1 1 calc R . . C19 C 1.3357(6) 0.8836(4) -0.0665(2) 0.0202(10) Uani 1 1 d . . . H19A H 1.2551 0.9545 -0.0938 0.024 Uiso 1 1 calc R . . H19B H 1.3596 0.9094 -0.0273 0.024 Uiso 1 1 calc R . . C20 C 1.5216(6) 0.8485(4) -0.1064(2) 0.0179(10) Uani 1 1 d . . . H20A H 1.4982 0.8220 -0.1454 0.022 Uiso 1 1 calc R . . H20B H 1.6030 0.7783 -0.0790 0.022 Uiso 1 1 calc R . . C21 C 1.6244(6) 0.9542(4) -0.1298(2) 0.0208(11) Uani 1 1 d . . . H21A H 1.5457 1.0226 -0.1592 0.025 Uiso 1 1 calc R . . H21B H 1.6414 0.9838 -0.0910 0.025 Uiso 1 1 calc R . . C22 C 1.8161(6) 0.9174(4) -0.1666(2) 0.0209(11) Uani 1 1 d . . . H22A H 1.7996 0.8889 -0.2058 0.025 Uiso 1 1 calc R . . H22B H 1.8951 0.8487 -0.1375 0.025 Uiso 1 1 calc R . . C23 C 1.9162(6) 1.0244(4) -0.1887(2) 0.0243(11) Uani 1 1 d . . . H23A H 1.8411 1.0915 -0.2190 0.036 Uiso 1 1 calc R . . H23B H 2.0368 0.9960 -0.2108 0.036 Uiso 1 1 calc R . . H23C H 1.9334 1.0529 -0.1501 0.036 Uiso 1 1 calc R . . C24 C -0.5695(6) 0.1706(4) 0.3065(2) 0.0195(10) Uani 1 1 d . . . C25 C -0.4968(6) 0.0503(4) 0.3002(2) 0.0189(10) Uani 1 1 d . . . H25 H -0.3774 0.0230 0.2804 0.023 Uiso 1 1 calc R . . C26 C -0.6226(7) -0.0289(4) 0.3271(2) 0.0220(11) Uani 1 1 d . . . H26 H -0.5929 -0.1133 0.3269 0.026 Uiso 1 1 calc R . . C27 C -0.7895(6) 0.0303(4) 0.3530(2) 0.0192(10) Uani 1 1 d . . . C28 C -0.9575(6) -0.0221(4) 0.3851(2) 0.0216(11) Uani 1 1 d . . . H28A H -0.9786 -0.0144 0.4315 0.026 Uiso 1 1 calc R . . H28B H -1.0689 0.0262 0.3621 0.026 Uiso 1 1 calc R . . C29 C -0.9286(7) -0.1575(4) 0.3823(2) 0.0227(11) Uani 1 1 d . . . H29A H -0.8176 -0.2051 0.4057 0.027 Uiso 1 1 calc R . . H29B H -0.9037 -0.1645 0.3358 0.027 Uiso 1 1 calc R . . C30 C -1.0943(6) -0.2158(4) 0.4125(2) 0.0212(11) Uani 1 1 d . . . H30A H -1.1181 -0.2121 0.4595 0.025 Uiso 1 1 calc R . . H30B H -1.2066 -0.1689 0.3897 0.025 Uiso 1 1 calc R . . C31 C -1.0528(7) -0.3506(4) 0.4060(2) 0.0230(11) Uani 1 1 d . . . H31A H -1.0269 -0.3529 0.3589 0.028 Uiso 1 1 calc R . . H31B H -0.9396 -0.3960 0.4287 0.028 Uiso 1 1 calc R . . C32 C -1.2097(7) -0.4170(4) 0.4344(2) 0.0223(11) Uani 1 1 d . . . H32A H -1.3240 -0.3709 0.4126 0.027 Uiso 1 1 calc R . . H32B H -1.2335 -0.4171 0.4818 0.027 Uiso 1 1 calc R . . C33 C -1.1657(7) -0.5509(4) 0.4255(2) 0.0224(11) Uani 1 1 d . . . H33A H -1.1439 -0.5502 0.3780 0.027 Uiso 1 1 calc R . . H33B H -1.0496 -0.5960 0.4464 0.027 Uiso 1 1 calc R . . C34 C -1.3184(7) -0.6212(4) 0.4546(2) 0.0233(11) Uani 1 1 d . . . H34A H -1.4341 -0.5779 0.4330 0.028 Uiso 1 1 calc R . . H34B H -1.3420 -0.6215 0.5020 0.028 Uiso 1 1 calc R . . C35 C -1.2657(7) -0.7560(4) 0.4455(2) 0.0248(11) Uani 1 1 d . . . H35A H -1.2434 -0.7554 0.3980 0.030 Uiso 1 1 calc R . . H35B H -1.1490 -0.7989 0.4665 0.030 Uiso 1 1 calc R . . C36 C -1.4167(7) -0.8282(4) 0.4752(3) 0.0300(12) Uani 1 1 d . . . H36A H -1.4402 -0.8290 0.5222 0.045 Uiso 1 1 calc R . . H36B H -1.3740 -0.9122 0.4690 0.045 Uiso 1 1 calc R . . H36C H -1.5309 -0.7890 0.4530 0.045 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 0.0117(6) 0.0149(6) 0.0292(7) -0.0085(5) 0.0086(5) -0.0038(5) S2 0.0120(6) 0.0143(6) 0.0297(7) -0.0090(5) 0.0086(5) -0.0035(5) S3 0.0121(6) 0.0161(6) 0.0301(7) -0.0099(5) 0.0094(5) -0.0046(5) S4 0.0146(6) 0.0177(6) 0.0331(7) -0.0098(5) 0.0103(5) -0.0051(5) O1 0.0187(18) 0.0225(18) 0.045(2) -0.0172(16) 0.0183(16) -0.0053(15) O2 0.0205(19) 0.0186(18) 0.050(2) -0.0187(16) 0.0166(16) -0.0056(15) C1 0.011(2) 0.020(2) 0.018(2) -0.0038(19) 0.0029(18) -0.0020(19) C2 0.016(2) 0.018(2) 0.025(3) -0.006(2) 0.0054(19) -0.005(2) C3 0.010(2) 0.017(2) 0.025(3) -0.0064(19) 0.0042(18) -0.0021(19) C4 0.009(2) 0.018(2) 0.024(3) -0.0061(19) 0.0014(19) -0.0061(19) C5 0.008(2) 0.016(2) 0.021(3) -0.0078(18) 0.0047(18) 0.0006(18) C6 0.011(2) 0.020(2) 0.022(3) -0.0095(19) 0.0042(19) -0.0020(19) C7 0.017(2) 0.019(3) 0.026(3) -0.010(2) 0.006(2) -0.005(2) C8 0.015(2) 0.019(2) 0.027(3) -0.009(2) 0.004(2) -0.003(2) C9 0.013(2) 0.014(2) 0.032(3) -0.008(2) 0.008(2) -0.0038(19) C10 0.011(2) 0.018(2) 0.018(2) -0.0045(18) 0.0026(18) -0.0026(19) C11 0.008(2) 0.020(2) 0.025(3) -0.0049(19) 0.0030(19) -0.0030(19) C12 0.016(2) 0.011(2) 0.030(3) -0.0084(19) 0.005(2) -0.0009(19) C13 0.016(3) 0.016(2) 0.032(3) -0.012(2) 0.007(2) -0.001(2) C14 0.006(2) 0.019(2) 0.024(3) -0.0044(19) 0.0048(18) -0.0027(18) C15 0.019(3) 0.017(2) 0.025(3) -0.0089(19) 0.005(2) -0.007(2) C16 0.008(2) 0.014(2) 0.028(3) -0.0052(19) 0.0021(19) -0.0009(18) C17 0.007(2) 0.026(3) 0.026(3) -0.006(2) 0.0055(19) -0.005(2) C18 0.007(2) 0.017(2) 0.030(3) -0.0087(19) 0.0085(19) -0.0048(18) C19 0.010(2) 0.021(2) 0.031(3) -0.012(2) 0.0072(19) -0.0037(19) C20 0.009(2) 0.021(2) 0.024(3) -0.0083(19) 0.0066(18) -0.0055(19) C21 0.018(3) 0.016(2) 0.030(3) -0.009(2) 0.003(2) -0.007(2) C22 0.015(2) 0.021(3) 0.026(3) -0.008(2) 0.006(2) -0.002(2) C23 0.015(2) 0.026(3) 0.032(3) -0.011(2) 0.010(2) -0.007(2) C24 0.014(2) 0.019(2) 0.024(3) -0.0056(19) 0.0072(19) -0.005(2) C25 0.008(2) 0.020(3) 0.027(3) -0.004(2) 0.0064(19) -0.0036(19) C26 0.024(3) 0.012(2) 0.030(3) -0.008(2) 0.006(2) -0.005(2) C27 0.015(2) 0.019(2) 0.023(3) -0.0043(19) 0.0046(19) -0.0047(19) C28 0.015(2) 0.020(2) 0.029(3) -0.009(2) 0.009(2) -0.005(2) C29 0.019(3) 0.019(2) 0.030(3) -0.008(2) 0.004(2) -0.004(2) C30 0.014(2) 0.019(2) 0.031(3) -0.008(2) 0.007(2) -0.004(2) C31 0.023(3) 0.018(2) 0.028(3) -0.005(2) 0.004(2) -0.006(2) C32 0.020(3) 0.017(2) 0.029(3) -0.008(2) 0.004(2) -0.004(2) C33 0.020(3) 0.023(3) 0.027(3) -0.010(2) 0.004(2) -0.008(2) C34 0.024(3) 0.024(3) 0.024(3) -0.008(2) 0.008(2) -0.011(2) C35 0.026(3) 0.018(2) 0.030(3) -0.007(2) 0.006(2) -0.009(2) C36 0.032(3) 0.020(3) 0.041(3) -0.014(2) 0.010(2) -0.010(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 C4 1.716(5) . ? S1 C1 1.760(4) . ? S2 C5 1.733(4) . ? S2 C10 1.742(4) . ? S3 C11 1.732(5) . ? S3 C14 1.736(4) . ? S4 C27 1.737(5) . ? S4 C24 1.739(4) . ? O1 C8 1.216(5) . ? O2 C7 1.205(5) . ? C1 C2 1.371(6) . ? C1 C24 1.446(6) . ? C2 C3 1.408(6) . ? C2 H2 0.9300 . ? C3 C4 1.397(6) . ? C3 C8 1.459(6) . ? C4 C5 1.444(6) . ? C5 C6 1.374(6) . ? C6 C9 1.414(6) . ? C6 C7 1.483(6) . ? C7 C8 1.558(6) . ? C9 C10 1.369(6) . ? C9 H9 0.9300 . ? C10 C11 1.449(6) . ? C11 C12 1.375(6) . ? C12 C13 1.431(6) . ? C12 H12 0.9300 . ? C13 C14 1.354(6) . ? C13 H13 0.9300 . ? C14 C15 1.504(6) . ? C15 C16 1.524(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.528(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.529(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.526(6) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.516(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.530(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.523(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.527(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.368(6) . ? C25 C26 1.423(6) . ? C25 H25 0.9300 . ? C26 C27 1.354(6) . ? C26 H26 0.9300 . ? C27 C28 1.514(6) . ? C28 C29 1.515(6) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.527(6) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.520(6) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.517(6) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.526(6) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.521(6) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.534(6) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.527(6) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 S1 C1 92.2(2) . . ? C5 S2 C10 91.9(2) . . ? C11 S3 C14 92.8(2) . . ? C27 S4 C24 92.1(2) . . ? C2 C1 C24 129.8(4) . . ? C2 C1 S1 109.9(3) . . ? C24 C1 S1 120.1(3) . . ? C1 C2 C3 114.2(4) . . ? C1 C2 H2 122.9 . . ? C3 C2 H2 122.9 . . ? C4 C3 C2 112.4(4) . . ? C4 C3 C8 121.3(4) . . ? C2 C3 C8 126.3(4) . . ? C3 C4 C5 121.0(4) . . ? C3 C4 S1 111.3(3) . . ? C5 C4 S1 127.7(3) . . ? C6 C5 C4 122.3(4) . . ? C6 C5 S2 110.7(3) . . ? C4 C5 S2 127.0(3) . . ? C5 C6 C9 113.4(4) . . ? C5 C6 C7 121.0(4) . . ? C9 C6 C7 125.5(4) . . ? O2 C7 C6 122.6(4) . . ? O2 C7 C8 120.8(4) . . ? C6 C7 C8 116.6(4) . . ? O1 C8 C3 123.6(4) . . ? O1 C8 C7 118.9(4) . . ? C3 C8 C7 117.6(4) . . ? C10 C9 C6 113.2(4) . . ? C10 C9 H9 123.4 . . ? C6 C9 H9 123.4 . . ? C9 C10 C11 126.9(4) . . ? C9 C10 S2 110.8(3) . . ? C11 C10 S2 122.2(3) . . ? C12 C11 C10 130.6(4) . . ? C12 C11 S3 110.2(3) . . ? C10 C11 S3 119.3(3) . . ? C11 C12 C13 112.8(4) . . ? C11 C12 H12 123.6 . . ? C13 C12 H12 123.6 . . ? C14 C13 C12 113.9(4) . . ? C14 C13 H13 123.0 . . ? C12 C13 H13 123.0 . . ? C13 C14 C15 132.0(4) . . ? C13 C14 S3 110.3(3) . . ? C15 C14 S3 117.7(3) . . ? C14 C15 C16 115.4(4) . . ? C14 C15 H15A 108.4 . . ? C16 C15 H15A 108.4 . . ? C14 C15 H15B 108.4 . . ? C16 C15 H15B 108.4 . . ? H15A C15 H15B 107.5 . . ? C15 C16 C17 110.4(4) . . ? C15 C16 H16A 109.6 . . ? C17 C16 H16A 109.6 . . ? C15 C16 H16B 109.6 . . ? C17 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? C16 C17 C18 114.1(4) . . ? C16 C17 H17A 108.7 . . ? C18 C17 H17A 108.7 . . ? C16 C17 H17B 108.7 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C19 C18 C17 113.4(4) . . ? C19 C18 H18A 108.9 . . ? C17 C18 H18A 108.9 . . ? C19 C18 H18B 108.9 . . ? C17 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? C20 C19 C18 114.3(4) . . ? C20 C19 H19A 108.7 . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19B 108.7 . . ? C18 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C19 C20 C21 113.8(4) . . ? C19 C20 H20A 108.8 . . ? C21 C20 H20A 108.8 . . ? C19 C20 H20B 108.8 . . ? C21 C20 H20B 108.8 . . ? H20A C20 H20B 107.7 . . ? C22 C21 C20 114.0(4) . . ? C22 C21 H21A 108.7 . . ? C20 C21 H21A 108.7 . . ? C22 C21 H21B 108.7 . . ? C20 C21 H21B 108.7 . . ? H21A C21 H21B 107.6 . . ? C21 C22 C23 112.8(4) . . ? C21 C22 H22A 109.0 . . ? C23 C22 H22A 109.0 . . ? C21 C22 H22B 109.0 . . ? C23 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C1 129.7(4) . . ? C25 C24 S4 110.4(3) . . ? C1 C24 S4 119.9(3) . . ? C24 C25 C26 113.1(4) . . ? C24 C25 H25 123.4 . . ? C26 C25 H25 123.4 . . ? C27 C26 C25 113.6(4) . . ? C27 C26 H26 123.2 . . ? C25 C26 H26 123.2 . . ? C26 C27 C28 128.8(4) . . ? C26 C27 S4 110.7(3) . . ? C28 C27 S4 120.4(3) . . ? C29 C28 C27 112.0(4) . . ? C29 C28 H28A 109.2 . . ? C27 C28 H28A 109.2 . . ? C29 C28 H28B 109.2 . . ? C27 C28 H28B 109.2 . . ? H28A C28 H28B 107.9 . . ? C28 C29 C30 114.8(4) . . ? C28 C29 H29A 108.6 . . ? C30 C29 H29A 108.6 . . ? C28 C29 H29B 108.6 . . ? C30 C29 H29B 108.6 . . ? H29A C29 H29B 107.5 . . ? C31 C30 C29 110.7(4) . . ? C31 C30 H30A 109.5 . . ? C29 C30 H30A 109.5 . . ? C31 C30 H30B 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 108.1 . . ? C32 C31 C30 114.9(4) . . ? C32 C31 H31A 108.6 . . ? C30 C31 H31A 108.6 . . ? C32 C31 H31B 108.6 . . ? C30 C31 H31B 108.6 . . ? H31A C31 H31B 107.5 . . ? C31 C32 C33 113.5(4) . . ? C31 C32 H32A 108.9 . . ? C33 C32 H32A 108.9 . . ? C31 C32 H32B 108.9 . . ? C33 C32 H32B 108.9 . . ? H32A C32 H32B 107.7 . . ? C34 C33 C32 115.0(4) . . ? C34 C33 H33A 108.5 . . ? C32 C33 H33A 108.5 . . ? C34 C33 H33B 108.5 . . ? C32 C33 H33B 108.5 . . ? H33A C33 H33B 107.5 . . ? C33 C34 C35 112.9(4) . . ? C33 C34 H34A 109.0 . . ? C35 C34 H34A 109.0 . . ? C33 C34 H34B 109.0 . . ? C35 C34 H34B 109.0 . . ? H34A C34 H34B 107.8 . . ? C36 C35 C34 113.5(4) . . ? C36 C35 H35A 108.9 . . ? C34 C35 H35A 108.9 . . ? C36 C35 H35B 108.9 . . ? C34 C35 H35B 108.9 . . ? H35A C35 H35B 107.7 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.924 _refine_diff_density_min -0.588 _refine_diff_density_rms 0.100 data_bhupi30 _database_code_depnum_ccdc_archive 'CCDC 914099' #TrackingRef '19d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Bis-(4-n-hexyl-thiophene-2-yl)-benzo[1,2-d:4,3-d']bis(thiazole)-4,5-dione ; _chemical_name_common ; 2,7-Bis-(4-n-hexyl-thiophene-2-yl)-benzo[1,2-d:4,3-d']bis(thiazole)-4,5-dione ; _chemical_melting_point ? _chemical_formula_moiety 'C28 H30 N2 O2 S4' _chemical_formula_sum 'C28 H30 N2 O2 S4' _chemical_formula_weight 554.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 _symmetry_space_group_name_Hall -P2ab2ac 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 5.4624(10) _cell_length_b 34.996(6) _cell_length_c 14.787(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2826.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1486 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 22.37 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.364 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 38099 _diffrn_reflns_av_R_equivalents 0.0625 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3242 _reflns_number_gt 2325 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0414P)^2^+0.9511P] 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 3242 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0881 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.98309(10) 0.215456(15) 0.30580(3) 0.04764(15) Uani 1 1 d . . . S2 S 1.55691(11) 0.139911(16) 0.40866(4) 0.05546(17) Uani 1 1 d . . . O1 O 0.9354(4) 0.22428(5) 0.63634(10) 0.0837(6) Uani 1 1 d . . . N1 N 1.1330(3) 0.19579(5) 0.46584(11) 0.0481(4) Uani 1 1 d . . . C1 C 1.1688(4) 0.18939(5) 0.37962(13) 0.0436(4) Uani 1 1 d . . . C2 C 0.9486(4) 0.22233(5) 0.47635(13) 0.0458(5) Uani 1 1 d . . . C3 C 0.8465(4) 0.23612(5) 0.39773(12) 0.0421(4) Uani 1 1 d . . . C4 C 0.8574(5) 0.23527(6) 0.56452(14) 0.0557(6) Uani 1 1 d . . . C5 C 1.3459(4) 0.16328(5) 0.34195(13) 0.0440(4) Uani 1 1 d . . . C6 C 1.3771(4) 0.15382(6) 0.25306(14) 0.0496(5) Uani 1 1 d . . . H6A H 1.2805 0.1638 0.2070 0.060 Uiso 1 1 calc R . . C7 C 1.5689(4) 0.12754(6) 0.23720(15) 0.0504(5) Uani 1 1 d . . . C8 C 1.6807(4) 0.11787(6) 0.31593(15) 0.0569(6) Uani 1 1 d . . . H8 H 1.8117 0.1009 0.3192 0.068 Uiso 1 1 calc R . . C9 C 1.6291(4) 0.11252(7) 0.14453(15) 0.0615(6) Uani 1 1 d . . . H9A H 1.7835 0.0989 0.1471 0.074 Uiso 1 1 calc R . . H9B H 1.6490 0.1339 0.1034 0.074 Uiso 1 1 calc R . . C10 C 1.4317(4) 0.08584(7) 0.10769(15) 0.0611(6) Uani 1 1 d . . . H10A H 1.4276 0.0629 0.1446 0.073 Uiso 1 1 calc R . . H10B H 1.2739 0.0983 0.1133 0.073 Uiso 1 1 calc R . . C11 C 1.4692(4) 0.07448(7) 0.01032(15) 0.0596(6) Uani 1 1 d . . . H11A H 1.6301 0.0630 0.0043 0.072 Uiso 1 1 calc R . . H11B H 1.4664 0.0973 -0.0268 0.072 Uiso 1 1 calc R . . C12 C 1.2807(4) 0.04676(7) -0.02546(15) 0.0600(6) Uani 1 1 d . . . H12A H 1.1189 0.0572 -0.0142 0.072 Uiso 1 1 calc R . . H12B H 1.2940 0.0230 0.0080 0.072 Uiso 1 1 calc R . . C13 C 1.3042(5) 0.03812(8) -0.12536(16) 0.0711(7) Uani 1 1 d . . . H13A H 1.2912 0.0618 -0.1590 0.085 Uiso 1 1 calc R . . H13B H 1.4655 0.0276 -0.1367 0.085 Uiso 1 1 calc R . . C14 C 1.1140(5) 0.01053(9) -0.16012(19) 0.0878(9) Uani 1 1 d . . . H14A H 1.1383 0.0065 -0.2237 0.132 Uiso 1 1 calc R . . H14B H 0.9536 0.0209 -0.1501 0.132 Uiso 1 1 calc R . . H14C H 1.1290 -0.0134 -0.1287 0.132 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 0.0530(3) 0.0541(3) 0.0358(2) 0.0016(2) -0.0001(2) 0.0090(2) S2 0.0574(3) 0.0617(3) 0.0473(3) 0.0015(2) -0.0102(2) 0.0095(3) O1 0.1248(16) 0.0869(12) 0.0395(9) 0.0018(8) -0.0094(9) 0.0406(12) N1 0.0572(11) 0.0471(9) 0.0401(9) -0.0005(7) -0.0064(8) 0.0031(8) C1 0.0455(11) 0.0425(10) 0.0429(11) 0.0015(8) -0.0029(8) -0.0028(9) C2 0.0583(12) 0.0403(10) 0.0389(10) -0.0020(8) -0.0050(9) 0.0017(9) C3 0.0502(11) 0.0402(10) 0.0361(9) -0.0005(7) -0.0008(8) -0.0026(8) C4 0.0799(16) 0.0508(12) 0.0363(10) 0.0006(9) -0.0035(10) 0.0081(11) C5 0.0432(11) 0.0452(10) 0.0437(10) 0.0019(8) -0.0020(9) 0.0004(9) C6 0.0475(12) 0.0555(12) 0.0457(11) 0.0043(9) -0.0022(9) 0.0053(10) C7 0.0448(12) 0.0558(12) 0.0506(12) -0.0002(9) 0.0030(10) 0.0006(10) C8 0.0483(12) 0.0617(13) 0.0608(14) -0.0022(11) -0.0049(10) 0.0107(11) C9 0.0504(13) 0.0771(15) 0.0569(14) -0.0067(12) 0.0094(11) 0.0054(12) C10 0.0587(14) 0.0734(15) 0.0513(13) -0.0046(11) 0.0102(11) 0.0012(12) C11 0.0531(13) 0.0782(15) 0.0476(12) -0.0040(11) 0.0077(10) 0.0033(12) C12 0.0528(13) 0.0729(15) 0.0544(13) -0.0023(11) 0.0084(11) 0.0037(12) C13 0.0559(15) 0.0996(19) 0.0579(14) -0.0118(14) 0.0056(12) -0.0052(14) C14 0.0766(19) 0.113(2) 0.0738(18) -0.0176(17) 0.0021(15) -0.0161(18) _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 1.7110(19) . ? S1 C1 1.747(2) . ? S2 C8 1.712(2) . ? S2 C5 1.724(2) . ? O1 C4 1.207(2) . ? N1 C1 1.309(2) . ? N1 C2 1.379(3) . ? C1 C5 1.443(3) . ? C2 C3 1.377(3) . ? C2 C4 1.467(3) . ? C3 C3 1.434(4) 2_655 ? C4 C4 1.562(4) 2_655 ? C5 C6 1.366(3) . ? C6 C7 1.414(3) . ? C6 H6A 0.9300 . ? C7 C8 1.357(3) . ? C7 C9 1.504(3) . ? C8 H8 0.9300 . ? C9 C10 1.526(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.508(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.510(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.513(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.509(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 S1 C1 88.71(9) . . ? C8 S2 C5 91.12(10) . . ? C1 N1 C2 109.51(16) . . ? N1 C1 C5 125.77(18) . . ? N1 C1 S1 115.62(15) . . ? C5 C1 S1 118.61(15) . . ? C3 C2 N1 115.91(17) . . ? C3 C2 C4 120.30(18) . . ? N1 C2 C4 123.78(17) . . ? C2 C3 C3 122.37(11) . 2_655 ? C2 C3 S1 110.25(14) . . ? C3 C3 S1 127.38(6) 2_655 . ? O1 C4 C2 124.3(2) . . ? O1 C4 C4 118.38(14) . 2_655 ? C2 C4 C4 117.31(11) . 2_655 ? C6 C5 C1 127.49(18) . . ? C6 C5 S2 110.62(15) . . ? C1 C5 S2 121.87(15) . . ? C5 C6 C7 114.19(19) . . ? C5 C6 H6A 122.9 . . ? C7 C6 H6A 122.9 . . ? C8 C7 C6 110.68(19) . . ? C8 C7 C9 126.6(2) . . ? C6 C7 C9 122.72(19) . . ? C7 C8 S2 113.38(17) . . ? C7 C8 H8 123.3 . . ? S2 C8 H8 123.3 . . ? C7 C9 C10 112.61(18) . . ? C7 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C7 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 113.96(19) . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10B 108.8 . . ? C9 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C10 C11 C12 114.29(19) . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? C12 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C11 C12 C13 114.35(19) . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12B 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C14 C13 C12 113.7(2) . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13B 108.8 . . ? C12 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.214 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.038 data_22 _database_code_depnum_ccdc_archive 'CCDC 914100' #TrackingRef '22.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Bis-(4-n-hexyl-5-trimethylsilylthiophen-2-yl)-benzo[1,2-d:4,3-d']bis(thiazole)-4,5-bis- (1,3-dioxolane) ; _chemical_name_common ; 2,7-Bis-(4-n-hexyl-5-trimethylsilylthiophen-2-yl)-benzo[1,2-d:4,3-d']bis(thiazole)-4,5-bis- (1,3-dioxolane) ; _chemical_melting_point ? _chemical_formula_moiety 'C38 H54 N2 O4 S4 Si2' _chemical_formula_sum 'C38 H54 N2 O4 S4 Si2' _chemical_formula_weight 787.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 '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 11.205(6) _cell_length_b 11.868(7) _cell_length_c 16.094(9) _cell_angle_alpha 103.904(11) _cell_angle_beta 97.871(11) _cell_angle_gamma 94.160(11) _cell_volume 2046(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4668 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 31.94 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.331 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9635 _exptl_absorpt_correction_T_max 0.9815 _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 "Bruker APEX II CCD 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 12012 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7118 _reflns_number_gt 5714 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _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^)+(0.0719P)^2^+0.3677P] 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 7118 _refine_ls_number_parameters 459 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0578 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1223 _refine_ls_wR_factor_gt 0.1115 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.72072(5) 0.55814(5) 0.27129(4) 0.01977(16) Uani 1 1 d . . . S2 S 0.40757(5) 0.56963(5) 0.08253(4) 0.01908(16) Uani 1 1 d . . . S3 S 0.12442(5) 0.45260(5) -0.06009(4) 0.02018(16) Uani 1 1 d . . . S4 S -0.18079(5) 0.18485(5) -0.18323(4) 0.02092(16) Uani 1 1 d . . . Si1 Si 0.92712(6) 0.71330(6) 0.40223(4) 0.02111(18) Uani 1 1 d . . . Si2 Si -0.40796(6) 0.12433(6) -0.32079(4) 0.01861(17) Uani 1 1 d . . . O1 O 0.20885(19) 0.07172(16) -0.00930(12) 0.0370(5) Uani 1 1 d . . . O2 O 0.18620(16) 0.20279(16) 0.11615(12) 0.0298(5) Uani 1 1 d . . . O3 O 0.42828(16) 0.17405(15) -0.01521(11) 0.0259(4) Uani 1 1 d . . . O4 O 0.42265(16) 0.17080(16) 0.12407(12) 0.0274(4) Uani 1 1 d . . . N1 N 0.51628(18) 0.40694(18) 0.13420(13) 0.0203(5) Uani 1 1 d . . . N2 N 0.06142(19) 0.23676(19) -0.06168(13) 0.0232(5) Uani 1 1 d . . . C1 C 0.8153(2) 0.6884(2) 0.29940(16) 0.0187(5) Uani 1 1 d . . . C2 C 0.7797(2) 0.7594(2) 0.24546(15) 0.0176(5) Uani 1 1 d . . . C3 C 0.6747(2) 0.7080(2) 0.18410(15) 0.0178(5) Uani 1 1 d . . . H3 H 0.6382 0.7448 0.1439 0.021 Uiso 1 1 calc R . . C4 C 0.6320(2) 0.5992(2) 0.18956(15) 0.0174(5) Uani 1 1 d . . . C5 C 0.5285(2) 0.5197(2) 0.13875(15) 0.0184(5) Uani 1 1 d . . . C6 C 0.4081(2) 0.3557(2) 0.08394(15) 0.0203(5) Uani 1 1 d . . . C7 C 0.3375(2) 0.4284(2) 0.05052(15) 0.0186(5) Uani 1 1 d . . . C8 C 0.2206(2) 0.3829(2) -0.00226(15) 0.0203(5) Uani 1 1 d . . . C9 C 0.1729(2) 0.2699(2) -0.01122(16) 0.0216(6) Uani 1 1 d . . . C10 C 0.2343(2) 0.1898(2) 0.03714(17) 0.0265(6) Uani 1 1 d . . . C11 C 0.3751(2) 0.2237(2) 0.05889(16) 0.0235(6) Uani 1 1 d . . . C12 C 0.0248(2) 0.3238(2) -0.09267(16) 0.0203(5) Uani 1 1 d . . . C13 C -0.0868(2) 0.3141(2) -0.15290(16) 0.0194(5) Uani 1 1 d . . . C14 C -0.1321(2) 0.3933(2) -0.19515(16) 0.0214(6) Uani 1 1 d . . . H14 H -0.0949 0.4688 -0.1860 0.026 Uiso 1 1 calc R . . C15 C -0.2408(2) 0.3492(2) -0.25402(15) 0.0189(5) Uani 1 1 d . . . C16 C -0.2803(2) 0.2350(2) -0.25471(16) 0.0187(5) Uani 1 1 d . . . C17 C -0.3053(2) 0.4182(2) -0.31075(17) 0.0263(6) Uani 1 1 d . . . H17A H -0.3914 0.4074 -0.3087 0.032 Uiso 1 1 calc R . . H17B H -0.2942 0.3854 -0.3701 0.032 Uiso 1 1 calc R . . C18 C -0.2650(2) 0.5487(2) -0.28741(18) 0.0267(6) Uani 1 1 d . . . H18A H -0.1781 0.5604 -0.2860 0.032 Uiso 1 1 calc R . . H18B H -0.2815 0.5833 -0.2297 0.032 Uiso 1 1 calc R . . C19 C -0.3276(2) 0.6120(2) -0.35060(19) 0.0302(6) Uani 1 1 d . . . H19A H -0.2899 0.6919 -0.3359 0.036 Uiso 1 1 calc R . . H19B H -0.3138 0.5749 -0.4086 0.036 Uiso 1 1 calc R . . C20 C -0.4632(3) 0.6138(3) -0.35169(18) 0.0301(6) Uani 1 1 d . . . H20A H -0.4778 0.6490 -0.2935 0.036 Uiso 1 1 calc R . . H20B H -0.5019 0.5341 -0.3686 0.036 Uiso 1 1 calc R . . C21 C -0.5213(3) 0.6812(3) -0.4135(2) 0.0394(7) Uani 1 1 d . . . H21A H -0.4808 0.7602 -0.3976 0.047 Uiso 1 1 calc R . . H21B H -0.5086 0.6447 -0.4719 0.047 Uiso 1 1 calc R . . C22 C -0.6560(3) 0.6867(4) -0.4132(2) 0.0555(10) Uani 1 1 d . . . H22A H -0.6974 0.6090 -0.4321 0.083 Uiso 1 1 calc R . . H22B H -0.6862 0.7321 -0.4519 0.083 Uiso 1 1 calc R . . H22C H -0.6696 0.7223 -0.3556 0.083 Uiso 1 1 calc R . . C23 C -0.3450(3) 0.0167(2) -0.40467(19) 0.0334(7) Uani 1 1 d . . . H23A H -0.4081 -0.0434 -0.4363 0.050 Uiso 1 1 calc R . . H23B H -0.2812 -0.0177 -0.3767 0.050 Uiso 1 1 calc R . . H23C H -0.3134 0.0560 -0.4439 0.050 Uiso 1 1 calc R . . C24 C -0.4677(2) 0.0441(2) -0.24570(18) 0.0268(6) Uani 1 1 d . . . H24A H -0.5049 0.0966 -0.2042 0.040 Uiso 1 1 calc R . . H24B H -0.4022 0.0138 -0.2160 0.040 Uiso 1 1 calc R . . H24C H -0.5267 -0.0192 -0.2784 0.040 Uiso 1 1 calc R . . C25 C -0.5302(2) 0.1920(2) -0.37532(17) 0.0232(6) Uani 1 1 d . . . H25A H -0.5974 0.1339 -0.4020 0.035 Uiso 1 1 calc R . . H25B H -0.4999 0.2238 -0.4189 0.035 Uiso 1 1 calc R . . H25C H -0.5563 0.2533 -0.3333 0.035 Uiso 1 1 calc R . . C26 C 0.8437(2) 0.8770(2) 0.24818(16) 0.0210(5) Uani 1 1 d . . . H26A H 0.8208 0.8943 0.1926 0.025 Uiso 1 1 calc R . . H26B H 0.9304 0.8721 0.2559 0.025 Uiso 1 1 calc R . . C27 C 0.8168(2) 0.9783(2) 0.31964(17) 0.0234(6) Uani 1 1 d . . . H27A H 0.8359 0.9603 0.3753 0.028 Uiso 1 1 calc R . . H27B H 0.7310 0.9873 0.3102 0.028 Uiso 1 1 calc R . . C28 C 0.8904(2) 1.0935(2) 0.32152(19) 0.0286(6) Uani 1 1 d . . . H28A H 0.8755 1.1533 0.3707 0.034 Uiso 1 1 calc R . . H28B H 0.9760 1.0835 0.3304 0.034 Uiso 1 1 calc R . . C29 C 0.8616(2) 1.1358(2) 0.2400(2) 0.0319(7) Uani 1 1 d . . . H29A H 0.7750 1.1396 0.2282 0.038 Uiso 1 1 calc R . . H29B H 0.8834 1.0794 0.1915 0.038 Uiso 1 1 calc R . . C30 C 0.9280(3) 1.2560(3) 0.2463(2) 0.0462(9) Uani 1 1 d . . . H30A H 0.9046 1.3129 0.2937 0.055 Uiso 1 1 calc R . . H30B H 1.0146 1.2529 0.2595 0.055 Uiso 1 1 calc R . . C31 C 0.9012(3) 1.2961(3) 0.1638(3) 0.0583(11) Uani 1 1 d . . . H31A H 0.9290 1.2429 0.1173 0.087 Uiso 1 1 calc R . . H31B H 0.9421 1.3729 0.1722 0.087 Uiso 1 1 calc R . . H31C H 0.8154 1.2980 0.1497 0.087 Uiso 1 1 calc R . . C32 C 1.0554(2) 0.8258(2) 0.40992(17) 0.0276(6) Uani 1 1 d . . . H32A H 1.1140 0.8289 0.4601 0.041 Uiso 1 1 calc R . . H32B H 1.0257 0.9006 0.4148 0.041 Uiso 1 1 calc R . . H32C H 1.0927 0.8060 0.3588 0.041 Uiso 1 1 calc R . . C33 C 0.8412(2) 0.7569(3) 0.49461(18) 0.0354(7) Uani 1 1 d . . . H33A H 0.8915 0.7560 0.5478 0.053 Uiso 1 1 calc R . . H33B H 0.7697 0.7029 0.4855 0.053 Uiso 1 1 calc R . . H33C H 0.8184 0.8341 0.4980 0.053 Uiso 1 1 calc R . . C34 C 0.9884(3) 0.5721(3) 0.4047(2) 0.0359(7) Uani 1 1 d . . . H34A H 1.0269 0.5464 0.3547 0.054 Uiso 1 1 calc R . . H34B H 0.9233 0.5146 0.4042 0.054 Uiso 1 1 calc R . . H34C H 1.0466 0.5827 0.4563 0.054 Uiso 1 1 calc R . . C35 C 0.5446(2) 0.1495(2) 0.11040(18) 0.0314(7) Uani 1 1 d . . . H35A H 0.5604 0.0720 0.1158 0.038 Uiso 1 1 calc R . . H35B H 0.6034 0.2066 0.1522 0.038 Uiso 1 1 calc R . . C36 C 0.5508(2) 0.1602(2) 0.01826(18) 0.0307(6) Uani 1 1 d . . . H36A H 0.6059 0.2275 0.0189 0.037 Uiso 1 1 calc R . . H36B H 0.5775 0.0906 -0.0163 0.037 Uiso 1 1 calc R . . C37 C 0.1708(4) 0.0081(3) 0.0462(3) 0.0702(14) Uani 1 1 d . . . H37A H 0.2266 -0.0489 0.0534 0.084 Uiso 1 1 calc R . . H37B H 0.0911 -0.0334 0.0217 0.084 Uiso 1 1 calc R . . C38 C 0.1661(3) 0.0879(3) 0.1306(2) 0.0404(8) Uani 1 1 d . . . H38A H 0.0878 0.0763 0.1483 0.048 Uiso 1 1 calc R . . H38B H 0.2288 0.0764 0.1748 0.048 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 0.0154(3) 0.0162(3) 0.0262(3) 0.0064(3) -0.0002(2) -0.0055(2) S2 0.0143(3) 0.0163(3) 0.0233(3) 0.0018(2) 0.0013(2) -0.0059(2) S3 0.0137(3) 0.0173(3) 0.0264(3) 0.0028(3) 0.0011(2) -0.0054(2) S4 0.0159(3) 0.0177(3) 0.0269(3) 0.0068(3) -0.0022(2) -0.0064(2) Si1 0.0131(4) 0.0255(4) 0.0232(4) 0.0073(3) -0.0004(3) -0.0052(3) Si2 0.0126(4) 0.0159(4) 0.0247(4) 0.0029(3) 0.0011(3) -0.0045(3) O1 0.0498(13) 0.0199(10) 0.0333(11) 0.0110(8) -0.0146(9) -0.0231(9) O2 0.0277(11) 0.0322(11) 0.0293(10) 0.0159(8) -0.0015(8) -0.0135(8) O3 0.0281(11) 0.0193(9) 0.0265(10) 0.0045(8) -0.0030(8) -0.0036(8) O4 0.0219(10) 0.0271(10) 0.0316(10) 0.0158(8) -0.0085(8) -0.0112(8) N1 0.0196(11) 0.0192(11) 0.0198(11) 0.0047(9) 0.0009(8) -0.0080(9) N2 0.0186(11) 0.0246(12) 0.0233(11) 0.0066(9) -0.0023(9) -0.0090(9) C1 0.0121(12) 0.0180(13) 0.0238(13) 0.0034(10) 0.0022(10) -0.0056(10) C2 0.0154(12) 0.0152(12) 0.0201(12) 0.0014(10) 0.0041(10) -0.0039(10) C3 0.0160(13) 0.0169(13) 0.0195(12) 0.0052(10) 0.0013(10) -0.0033(10) C4 0.0126(12) 0.0165(12) 0.0213(12) 0.0025(10) 0.0026(10) -0.0029(10) C5 0.0146(13) 0.0209(13) 0.0179(12) 0.0022(10) 0.0044(10) -0.0048(10) C6 0.0178(13) 0.0217(13) 0.0182(12) 0.0045(10) -0.0005(10) -0.0097(10) C7 0.0146(13) 0.0195(13) 0.0189(12) 0.0028(10) 0.0020(9) -0.0085(10) C8 0.0203(14) 0.0208(13) 0.0177(12) 0.0031(10) 0.0027(10) -0.0053(10) C9 0.0185(13) 0.0229(14) 0.0208(13) 0.0067(11) -0.0011(10) -0.0099(11) C10 0.0284(15) 0.0210(14) 0.0254(14) 0.0082(11) -0.0065(11) -0.0151(11) C11 0.0260(15) 0.0182(13) 0.0236(13) 0.0082(11) -0.0044(11) -0.0093(11) C12 0.0158(13) 0.0199(13) 0.0219(13) 0.0017(10) 0.0023(10) -0.0056(10) C13 0.0142(13) 0.0178(13) 0.0229(13) 0.0014(10) 0.0024(10) -0.0051(10) C14 0.0198(13) 0.0145(12) 0.0269(13) 0.0025(10) 0.0023(10) -0.0059(10) C15 0.0160(13) 0.0161(12) 0.0228(13) 0.0024(10) 0.0040(10) -0.0034(10) C16 0.0142(12) 0.0187(13) 0.0216(13) 0.0032(10) 0.0031(10) -0.0028(10) C17 0.0272(15) 0.0183(14) 0.0321(15) 0.0079(11) 0.0003(11) -0.0031(11) C18 0.0200(14) 0.0191(14) 0.0414(16) 0.0099(12) 0.0051(12) -0.0035(11) C19 0.0295(16) 0.0199(14) 0.0440(17) 0.0134(12) 0.0090(13) -0.0024(12) C20 0.0305(16) 0.0304(16) 0.0338(15) 0.0130(12) 0.0102(12) 0.0052(12) C21 0.0439(19) 0.0355(17) 0.0453(18) 0.0206(14) 0.0088(15) 0.0088(14) C22 0.052(2) 0.072(3) 0.054(2) 0.0310(19) 0.0057(17) 0.029(2) C23 0.0228(15) 0.0270(15) 0.0421(17) -0.0052(13) 0.0063(12) -0.0061(12) C24 0.0160(13) 0.0253(14) 0.0392(16) 0.0152(12) -0.0035(11) -0.0052(11) C25 0.0195(14) 0.0230(14) 0.0260(13) 0.0068(11) 0.0021(10) -0.0035(11) C26 0.0171(13) 0.0172(13) 0.0268(13) 0.0053(10) 0.0010(10) -0.0057(10) C27 0.0152(13) 0.0181(13) 0.0340(15) 0.0034(11) 0.0019(11) -0.0016(10) C28 0.0177(14) 0.0157(13) 0.0459(17) 0.0000(12) -0.0003(12) -0.0036(11) C29 0.0187(14) 0.0151(14) 0.0597(19) 0.0112(13) -0.0004(13) -0.0050(11) C30 0.0309(18) 0.0221(16) 0.085(3) 0.0201(16) 0.0019(16) -0.0078(13) C31 0.0317(19) 0.040(2) 0.114(3) 0.049(2) -0.0010(19) -0.0086(15) C32 0.0157(14) 0.0359(16) 0.0282(14) 0.0077(12) -0.0010(11) -0.0063(12) C33 0.0177(14) 0.058(2) 0.0260(15) 0.0080(14) 0.0013(11) -0.0096(13) C34 0.0298(16) 0.0361(17) 0.0439(17) 0.0202(14) -0.0029(13) -0.0005(13) C35 0.0229(15) 0.0260(15) 0.0430(17) 0.0159(13) -0.0097(12) -0.0085(12) C36 0.0257(16) 0.0214(14) 0.0432(17) 0.0117(12) -0.0026(12) -0.0063(12) C37 0.096(3) 0.0281(19) 0.116(4) 0.035(2) 0.082(3) 0.0186(19) C38 0.0247(16) 0.0429(19) 0.061(2) 0.0382(17) -0.0036(14) -0.0101(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 C4 1.725(3) . ? S1 C1 1.736(2) . ? S2 C7 1.725(3) . ? S2 C5 1.745(3) . ? S3 C8 1.714(3) . ? S3 C12 1.751(3) . ? S4 C13 1.723(2) . ? S4 C16 1.731(3) . ? Si1 C32 1.859(3) . ? Si1 C34 1.863(3) . ? Si1 C33 1.870(3) . ? Si1 C1 1.882(3) . ? Si2 C25 1.860(3) . ? Si2 C24 1.870(3) . ? Si2 C23 1.875(3) . ? Si2 C16 1.882(3) . ? O1 C37 1.390(4) . ? O1 C10 1.409(3) . ? O2 C10 1.427(3) . ? O2 C38 1.445(3) . ? O3 C11 1.426(3) . ? O3 C36 1.441(3) . ? O4 C11 1.411(3) . ? O4 C35 1.444(3) . ? N1 C5 1.318(3) . ? N1 C6 1.371(3) . ? N2 C12 1.318(3) . ? N2 C9 1.368(3) . ? C1 C2 1.388(4) . ? C2 C3 1.422(3) . ? C2 C26 1.510(3) . ? C3 C4 1.371(3) . ? C3 H3 0.9300 . ? C4 C5 1.455(3) . ? C6 C7 1.366(4) . ? C6 C11 1.525(3) . ? C7 C8 1.449(3) . ? C8 C9 1.373(4) . ? C9 C10 1.512(4) . ? C10 C11 1.569(4) . ? C12 C13 1.452(4) . ? C13 C14 1.372(4) . ? C14 C15 1.418(3) . ? C14 H14 0.9300 . ? C15 C16 1.391(4) . ? C15 C17 1.514(4) . ? C17 C18 1.522(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.530(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.519(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.528(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.516(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C27 1.530(4) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.537(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.517(4) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.535(4) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.514(5) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 C36 1.529(4) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.468(5) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 H38A 0.9700 . ? C38 H38B 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 92.53(12) . . ? C7 S2 C5 88.49(12) . . ? C8 S3 C12 88.41(13) . . ? C13 S4 C16 92.88(12) . . ? C32 Si1 C34 108.84(14) . . ? C32 Si1 C33 110.86(13) . . ? C34 Si1 C33 109.31(15) . . ? C32 Si1 C1 112.91(12) . . ? C34 Si1 C1 107.77(13) . . ? C33 Si1 C1 107.06(13) . . ? C25 Si2 C24 111.09(12) . . ? C25 Si2 C23 109.31(14) . . ? C24 Si2 C23 107.93(14) . . ? C25 Si2 C16 112.63(12) . . ? C24 Si2 C16 107.15(12) . . ? C23 Si2 C16 108.59(12) . . ? C37 O1 C10 108.2(2) . . ? C10 O2 C38 107.5(2) . . ? C11 O3 C36 105.47(19) . . ? C11 O4 C35 106.5(2) . . ? C5 N1 C6 110.0(2) . . ? C12 N2 C9 110.0(2) . . ? C2 C1 S1 110.64(18) . . ? C2 C1 Si1 133.25(18) . . ? S1 C1 Si1 115.47(14) . . ? C1 C2 C3 112.2(2) . . ? C1 C2 C26 125.5(2) . . ? C3 C2 C26 122.3(2) . . ? C4 C3 C2 113.8(2) . . ? C4 C3 H3 123.1 . . ? C2 C3 H3 123.1 . . ? C3 C4 C5 130.2(2) . . ? C3 C4 S1 110.77(18) . . ? C5 C4 S1 119.07(19) . . ? N1 C5 C4 123.3(2) . . ? N1 C5 S2 115.17(18) . . ? C4 C5 S2 121.48(19) . . ? C7 C6 N1 116.0(2) . . ? C7 C6 C11 121.8(2) . . ? N1 C6 C11 121.8(2) . . ? C6 C7 C8 120.2(2) . . ? C6 C7 S2 110.35(18) . . ? C8 C7 S2 129.4(2) . . ? C9 C8 C7 120.8(2) . . ? C9 C8 S3 110.67(19) . . ? C7 C8 S3 128.5(2) . . ? N2 C9 C8 115.8(2) . . ? N2 C9 C10 121.7(2) . . ? C8 C9 C10 122.4(2) . . ? O1 C10 O2 107.7(2) . . ? O1 C10 C9 112.0(2) . . ? O2 C10 C9 106.9(2) . . ? O1 C10 C11 109.6(2) . . ? O2 C10 C11 109.03(19) . . ? C9 C10 C11 111.5(2) . . ? O4 C11 O3 105.7(2) . . ? O4 C11 C6 112.50(19) . . ? O3 C11 C6 108.8(2) . . ? O4 C11 C10 108.8(2) . . ? O3 C11 C10 109.04(19) . . ? C6 C11 C10 111.8(2) . . ? N2 C12 C13 123.5(2) . . ? N2 C12 S3 115.14(19) . . ? C13 C12 S3 121.34(19) . . ? C14 C13 C12 130.1(2) . . ? C14 C13 S4 110.60(18) . . ? C12 C13 S4 119.28(19) . . ? C13 C14 C15 113.7(2) . . ? C13 C14 H14 123.1 . . ? C15 C14 H14 123.1 . . ? C16 C15 C14 112.5(2) . . ? C16 C15 C17 124.0(2) . . ? C14 C15 C17 123.6(2) . . ? C15 C16 S4 110.29(18) . . ? C15 C16 Si2 134.2(2) . . ? S4 C16 Si2 115.33(14) . . ? C15 C17 C18 116.1(2) . . ? C15 C17 H17A 108.3 . . ? C18 C17 H17A 108.3 . . ? C15 C17 H17B 108.3 . . ? C18 C17 H17B 108.3 . . ? H17A C17 H17B 107.4 . . ? C17 C18 C19 113.5(2) . . ? C17 C18 H18A 108.9 . . ? C19 C18 H18A 108.9 . . ? C17 C18 H18B 108.9 . . ? C19 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? C20 C19 C18 114.9(2) . . ? C20 C19 H19A 108.5 . . ? C18 C19 H19A 108.5 . . ? C20 C19 H19B 108.5 . . ? C18 C19 H19B 108.5 . . ? H19A C19 H19B 107.5 . . ? C19 C20 C21 113.2(2) . . ? C19 C20 H20A 108.9 . . ? C21 C20 H20A 108.9 . . ? C19 C20 H20B 108.9 . . ? C21 C20 H20B 108.9 . . ? H20A C20 H20B 107.8 . . ? C22 C21 C20 113.7(3) . . ? C22 C21 H21A 108.8 . . ? C20 C21 H21A 108.8 . . ? C22 C21 H21B 108.8 . . ? C20 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? Si2 C23 H23A 109.5 . . ? Si2 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? Si2 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? Si2 C24 H24A 109.5 . . ? Si2 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? Si2 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? Si2 C25 H25A 109.5 . . ? Si2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? Si2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C2 C26 C27 114.8(2) . . ? C2 C26 H26A 108.6 . . ? C27 C26 H26A 108.6 . . ? C2 C26 H26B 108.6 . . ? C27 C26 H26B 108.6 . . ? H26A C26 H26B 107.5 . . ? C26 C27 C28 111.8(2) . . ? C26 C27 H27A 109.3 . . ? C28 C27 H27A 109.3 . . ? C26 C27 H27B 109.3 . . ? C28 C27 H27B 109.3 . . ? H27A C27 H27B 107.9 . . ? C29 C28 C27 114.3(2) . . ? C29 C28 H28A 108.7 . . ? C27 C28 H28A 108.7 . . ? C29 C28 H28B 108.7 . . ? C27 C28 H28B 108.7 . . ? H28A C28 H28B 107.6 . . ? C28 C29 C30 113.4(2) . . ? C28 C29 H29A 108.9 . . ? C30 C29 H29A 108.9 . . ? C28 C29 H29B 108.9 . . ? C30 C29 H29B 108.9 . . ? H29A C29 H29B 107.7 . . ? C31 C30 C29 113.1(3) . . ? C31 C30 H30A 109.0 . . ? C29 C30 H30A 109.0 . . ? C31 C30 H30B 109.0 . . ? C29 C30 H30B 109.0 . . ? H30A C30 H30B 107.8 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? Si1 C32 H32A 109.5 . . ? Si1 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? Si1 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? Si1 C33 H33A 109.5 . . ? Si1 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? Si1 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? Si1 C34 H34A 109.5 . . ? Si1 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? Si1 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O4 C35 C36 105.1(2) . . ? O4 C35 H35A 110.7 . . ? C36 C35 H35A 110.7 . . ? O4 C35 H35B 110.7 . . ? C36 C35 H35B 110.7 . . ? H35A C35 H35B 108.8 . . ? O3 C36 C35 104.1(2) . . ? O3 C36 H36A 110.9 . . ? C35 C36 H36A 110.9 . . ? O3 C36 H36B 110.9 . . ? C35 C36 H36B 110.9 . . ? H36A C36 H36B 109.0 . . ? O1 C37 C38 109.3(3) . . ? O1 C37 H37A 109.8 . . ? C38 C37 H37A 109.8 . . ? O1 C37 H37B 109.8 . . ? C38 C37 H37B 109.8 . . ? H37A C37 H37B 108.3 . . ? O2 C38 C37 104.1(2) . . ? O2 C38 H38A 110.9 . . ? C37 C38 H38A 110.9 . . ? O2 C38 H38B 110.9 . . ? C37 C38 H38B 110.9 . . ? H38A C38 H38B 108.9 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.540 _refine_diff_density_min -0.485 _refine_diff_density_rms 0.072 data_p _database_code_depnum_ccdc_archive 'CCDC 914101' #TrackingRef '24.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Bis-(thiophen-2-yl)-benzo[1,2-d:4,3-d']bis(thiazole)-4,5-bis-(1,3-dioxolane) ; _chemical_name_common ; 2,7-Bis-(thiophen-2-yl)-benzo[1,2-d:4,3-d']bis(thiazole)-4,5-bis-(1,3-dioxolane) ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 N2 O4 S4' _chemical_formula_sum 'C20 H14 N2 O4 S4' _chemical_formula_weight 474.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 _symmetry_space_group_name_Hall -P2ybc 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 7.4786(8) _cell_length_b 21.309(2) _cell_length_c 12.5339(13) _cell_angle_alpha 90.00 _cell_angle_beta 94.645(2) _cell_angle_gamma 90.00 _cell_volume 1990.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3849 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 23.10 _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.510 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9701 _exptl_absorpt_correction_T_max 0.9849 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23402 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3497 _reflns_number_gt 2759 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0392P)^2^+1.7089P] 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 3497 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0976 _refine_ls_wR_factor_gt 0.0886 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.004 _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 0.84884(10) 0.60841(3) 0.13194(5) 0.03497(19) Uani 1 1 d . . . S2 S 0.75851(10) 0.46697(3) -0.02269(5) 0.03553(19) Uani 1 1 d . . . S3 S 0.56377(12) 0.27734(4) -0.09402(7) 0.0479(2) Uani 1 1 d . . . S4 S 0.88997(15) 0.72560(4) 0.41856(7) 0.0634(3) Uani 1 1 d . . . O1 O 0.8650(2) 0.43953(9) 0.35502(15) 0.0351(4) Uani 1 1 d . . . O2 O 0.6404(3) 0.48952(9) 0.43324(14) 0.0377(5) Uani 1 1 d . . . O3 O 0.5346(3) 0.38136(8) 0.30733(15) 0.0371(5) Uani 1 1 d . . . O4 O 0.4057(2) 0.47444(8) 0.25470(15) 0.0335(4) Uani 1 1 d . . . N1 N 0.8092(3) 0.59117(10) 0.33259(17) 0.0311(5) Uani 1 1 d . . . N2 N 0.5856(3) 0.38516(10) 0.08133(18) 0.0326(5) Uani 1 1 d . . . C1 C 0.8576(3) 0.63340(12) 0.2648(2) 0.0305(6) Uani 1 1 d . . . C2 C 0.7630(3) 0.53676(12) 0.2801(2) 0.0269(6) Uani 1 1 d . . . C3 C 0.7767(3) 0.53650(12) 0.1722(2) 0.0283(6) Uani 1 1 d . . . C4 C 0.7247(3) 0.48179(12) 0.1084(2) 0.0294(6) Uani 1 1 d . . . C5 C 0.6330(3) 0.43339(12) 0.1499(2) 0.0288(6) Uani 1 1 d . . . C6 C 0.5695(3) 0.43993(12) 0.2614(2) 0.0287(6) Uani 1 1 d . . . C7 C 0.7087(3) 0.47722(12) 0.3354(2) 0.0284(6) Uani 1 1 d . . . C8 C 0.8572(5) 0.41233(16) 0.4590(2) 0.0515(8) Uani 1 1 d . . . H8A H 0.9780 0.4104 0.4975 0.062 Uiso 1 1 calc R . . H8B H 0.8061 0.3695 0.4538 0.062 Uiso 1 1 calc R . . C9 C 0.7383(6) 0.4554(2) 0.5137(3) 0.0733(12) Uani 1 1 d . . . H9A H 0.6564 0.4313 0.5564 0.088 Uiso 1 1 calc R . . H9B H 0.8104 0.4841 0.5622 0.088 Uiso 1 1 calc R . . C10 C 0.3518(4) 0.38150(17) 0.3346(3) 0.0559(9) Uani 1 1 d . . . H10A H 0.3434 0.3944 0.4100 0.067 Uiso 1 1 calc R . . H10B H 0.2958 0.3397 0.3232 0.067 Uiso 1 1 calc R . . C11 C 0.2664(4) 0.42908(15) 0.2585(3) 0.0506(8) Uani 1 1 d . . . H11A H 0.2344 0.4105 0.1871 0.061 Uiso 1 1 calc R . . H11B H 0.1578 0.4475 0.2861 0.061 Uiso 1 1 calc R . . C12 C 0.6421(4) 0.39608(12) -0.0129(2) 0.0315(6) Uani 1 1 d . . . C13 C 0.6185(4) 0.35544(12) -0.1061(2) 0.0334(6) Uani 1 1 d . . . C14 C 0.6289(4) 0.37127(13) -0.2109(2) 0.0381(7) Uani 1 1 d . . . H14A H 0.6578 0.4122 -0.2341 0.046 Uiso 1 1 calc R . . C15 C 0.5925(4) 0.32051(14) -0.2806(2) 0.0440(7) Uani 1 1 d . . . H15A H 0.5934 0.3236 -0.3562 0.053 Uiso 1 1 calc R . . C16 C 0.5563(4) 0.26712(14) -0.2299(2) 0.0459(8) Uani 1 1 d . . . H16 H 0.5297 0.2283 -0.2651 0.055 Uiso 1 1 calc R . . C17 C 0.9142(3) 0.69694(12) 0.2928(2) 0.0323(6) Uani 1 1 d . . . C19 C 1.0327(4) 0.79707(15) 0.2874(3) 0.0506(8) Uani 1 1 d . . . H19A H 1.0878 0.8327 0.2583 0.061 Uiso 1 1 calc R . . C18 C 0.9906(4) 0.74139(12) 0.2269(3) 0.0391(7) Uani 1 1 d . . . H18 H 1.0110 0.7353 0.1538 0.047 Uiso 1 1 calc R . . C20 C 0.9878(5) 0.79463(16) 0.3883(3) 0.0583(9) Uani 1 1 d . . . H20 H 1.0084 0.8280 0.4380 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 0.0448(4) 0.0296(4) 0.0313(4) -0.0008(3) 0.0083(3) -0.0087(3) S2 0.0439(4) 0.0341(4) 0.0295(4) -0.0054(3) 0.0085(3) -0.0080(3) S3 0.0636(5) 0.0314(4) 0.0484(5) -0.0018(3) 0.0029(4) -0.0085(4) S4 0.0996(8) 0.0453(5) 0.0454(5) -0.0106(4) 0.0056(5) -0.0101(5) O1 0.0308(10) 0.0393(11) 0.0352(10) 0.0050(9) 0.0022(8) 0.0090(8) O2 0.0478(12) 0.0393(11) 0.0277(10) 0.0032(8) 0.0125(9) 0.0060(9) O3 0.0404(11) 0.0276(10) 0.0444(11) 0.0054(9) 0.0109(9) -0.0024(8) O4 0.0245(9) 0.0330(10) 0.0436(11) 0.0024(8) 0.0065(8) 0.0005(8) N1 0.0317(12) 0.0303(12) 0.0311(12) -0.0022(10) 0.0009(10) -0.0004(9) N2 0.0330(12) 0.0287(12) 0.0361(13) -0.0026(10) 0.0026(10) -0.0015(10) C1 0.0298(14) 0.0288(14) 0.0329(14) -0.0018(12) 0.0020(11) -0.0014(11) C2 0.0244(13) 0.0289(14) 0.0275(13) -0.0001(11) 0.0032(10) 0.0013(11) C3 0.0290(14) 0.0269(14) 0.0298(14) -0.0011(11) 0.0064(11) -0.0018(11) C4 0.0288(14) 0.0288(14) 0.0313(14) -0.0028(11) 0.0062(11) -0.0003(11) C5 0.0265(13) 0.0290(14) 0.0306(14) 0.0000(11) 0.0010(11) 0.0013(11) C6 0.0281(13) 0.0234(13) 0.0349(15) 0.0041(11) 0.0053(11) -0.0006(11) C7 0.0278(13) 0.0301(14) 0.0281(14) 0.0022(11) 0.0067(11) 0.0053(11) C8 0.059(2) 0.054(2) 0.0400(18) 0.0155(15) -0.0048(16) 0.0095(16) C9 0.092(3) 0.096(3) 0.0318(18) 0.0125(19) 0.0058(18) 0.036(2) C10 0.0463(19) 0.053(2) 0.071(2) 0.0126(18) 0.0215(17) -0.0120(16) C11 0.0323(16) 0.050(2) 0.071(2) 0.0005(17) 0.0111(15) -0.0090(14) C12 0.0302(14) 0.0295(14) 0.0347(15) -0.0035(12) 0.0014(12) 0.0005(11) C13 0.0319(15) 0.0285(14) 0.0396(16) -0.0050(12) 0.0018(12) 0.0010(11) C14 0.0465(17) 0.0294(15) 0.0380(16) -0.0036(12) 0.0011(13) 0.0019(13) C15 0.0547(19) 0.0394(17) 0.0366(16) -0.0092(13) -0.0048(14) 0.0046(14) C16 0.0523(19) 0.0348(17) 0.0494(19) -0.0127(14) -0.0035(15) -0.0012(14) C17 0.0299(14) 0.0301(14) 0.0359(15) -0.0041(12) -0.0029(12) 0.0005(11) C19 0.0485(19) 0.0331(17) 0.069(2) 0.0001(16) 0.0000(17) -0.0063(14) C18 0.0356(15) 0.0245(14) 0.0571(19) -0.0073(13) 0.0029(14) -0.0070(12) C20 0.072(2) 0.0382(18) 0.062(2) -0.0147(17) -0.0088(19) -0.0045(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C3 1.714(3) . ? S1 C1 1.745(3) . ? S2 C4 1.711(3) . ? S2 C12 1.753(3) . ? S3 C16 1.713(3) . ? S3 C13 1.723(3) . ? S4 C20 1.700(4) . ? S4 C17 1.714(3) . ? O1 C7 1.423(3) . ? O1 C8 1.432(3) . ? O2 C7 1.391(3) . ? O2 C9 1.401(4) . ? O3 C6 1.408(3) . ? O3 C10 1.436(4) . ? O4 C11 1.425(3) . ? O4 C6 1.425(3) . ? N1 C1 1.309(3) . ? N1 C2 1.364(3) . ? N2 C12 1.307(3) . ? N2 C5 1.368(3) . ? C1 C17 1.453(4) . ? C2 C3 1.364(3) . ? C2 C7 1.517(4) . ? C3 C4 1.449(4) . ? C4 C5 1.365(4) . ? C5 C6 1.518(4) . ? C6 C7 1.556(4) . ? C8 C9 1.484(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.499(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.453(4) . ? C13 C14 1.364(4) . ? C14 C15 1.404(4) . ? C14 H14A 0.9500 . ? C15 C16 1.342(4) . ? C15 H15A 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.408(4) . ? C19 C20 1.336(5) . ? C19 C18 1.429(4) . ? C19 H19A 0.9500 . ? C18 H18 0.9500 . ? C20 H20 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 S1 C1 88.86(12) . . ? C4 S2 C12 88.79(13) . . ? C16 S3 C13 91.40(14) . . ? C20 S4 C17 91.34(16) . . ? C7 O1 C8 107.0(2) . . ? C7 O2 C9 109.2(2) . . ? C6 O3 C10 107.9(2) . . ? C11 O4 C6 106.0(2) . . ? C1 N1 C2 110.1(2) . . ? C12 N2 C5 110.4(2) . . ? N1 C1 C17 125.1(2) . . ? N1 C1 S1 114.77(19) . . ? C17 C1 S1 120.1(2) . . ? N1 C2 C3 116.5(2) . . ? N1 C2 C7 123.8(2) . . ? C3 C2 C7 119.6(2) . . ? C2 C3 C4 120.8(2) . . ? C2 C3 S1 109.81(19) . . ? C4 C3 S1 129.3(2) . . ? C5 C4 C3 121.2(2) . . ? C5 C4 S2 110.15(19) . . ? C3 C4 S2 128.6(2) . . ? C4 C5 N2 116.1(2) . . ? C4 C5 C6 119.1(2) . . ? N2 C5 C6 124.3(2) . . ? O3 C6 O4 107.16(19) . . ? O3 C6 C5 112.2(2) . . ? O4 C6 C5 108.9(2) . . ? O3 C6 C7 110.2(2) . . ? O4 C6 C7 107.6(2) . . ? C5 C6 C7 110.6(2) . . ? O2 C7 O1 108.0(2) . . ? O2 C7 C2 112.1(2) . . ? O1 C7 C2 107.7(2) . . ? O2 C7 C6 110.2(2) . . ? O1 C7 C6 108.4(2) . . ? C2 C7 C6 110.2(2) . . ? O1 C8 C9 103.9(2) . . ? O1 C8 H8A 111.0 . . ? C9 C8 H8A 111.0 . . ? O1 C8 H8B 111.0 . . ? C9 C8 H8B 111.0 . . ? H8A C8 H8B 109.0 . . ? O2 C9 C8 106.6(3) . . ? O2 C9 H9A 110.4 . . ? C8 C9 H9A 110.4 . . ? O2 C9 H9B 110.4 . . ? C8 C9 H9B 110.4 . . ? H9A C9 H9B 108.6 . . ? O3 C10 C11 102.4(2) . . ? O3 C10 H10A 111.3 . . ? C11 C10 H10A 111.3 . . ? O3 C10 H10B 111.3 . . ? C11 C10 H10B 111.3 . . ? H10A C10 H10B 109.2 . . ? O4 C11 C10 101.8(2) . . ? O4 C11 H11A 111.4 . . ? C10 C11 H11A 111.4 . . ? O4 C11 H11B 111.4 . . ? C10 C11 H11B 111.4 . . ? H11A C11 H11B 109.3 . . ? N2 C12 C13 126.4(2) . . ? N2 C12 S2 114.55(19) . . ? C13 C12 S2 119.1(2) . . ? C14 C13 C12 127.9(3) . . ? C14 C13 S3 110.8(2) . . ? C12 C13 S3 121.3(2) . . ? C13 C14 C15 112.7(3) . . ? C13 C14 H14A 123.6 . . ? C15 C14 H14A 123.6 . . ? C16 C15 C14 113.2(3) . . ? C16 C15 H15A 123.4 . . ? C14 C15 H15A 123.4 . . ? C15 C16 S3 111.8(2) . . ? C15 C16 H16 124.1 . . ? S3 C16 H16 124.1 . . ? C18 C17 C1 127.6(3) . . ? C18 C17 S4 112.2(2) . . ? C1 C17 S4 120.2(2) . . ? C20 C19 C18 114.1(3) . . ? C20 C19 H19A 123.0 . . ? C18 C19 H19A 123.0 . . ? C17 C18 C19 109.3(3) . . ? C17 C18 H18 125.4 . . ? C19 C18 H18 125.4 . . ? C19 C20 S4 113.0(3) . . ? C19 C20 H20 123.5 . . ? S4 C20 H20 123.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.361 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.053 data_12 _database_code_depnum_ccdc_archive 'CCDC 914102' #TrackingRef '26b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(5-Pentafluorobenzoyl-thiophen-2-yl)-7-(thiophen-2-yl)-benzo[1,2-d:4,3-d']bis(thiazole)- 4,5-bis-(1,3-dioxolane) ; _chemical_name_common ; 2-(5-Pentafluorobenzoyl-thiophen-2-yl)-7-(thiophen-2-yl)-benzo[1,2-d:4,3-d']bis(thiazole)- 4,5-bis-(1,3-dioxolane) ; _chemical_melting_point ? _chemical_formula_moiety 'C27 H13 F5 N2 O5 S4' _chemical_formula_sum 'C27 H13 F5 N2 O5 S4' _chemical_formula_weight 668.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c 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' '-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 40.227(8) _cell_length_b 7.2753(15) _cell_length_c 20.654(4) _cell_angle_alpha 90.00 _cell_angle_beta 116.42(3) _cell_angle_gamma 90.00 _cell_volume 5413.6(19) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.641 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2704 _exptl_absorpt_coefficient_mu 0.429 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.317 _exptl_absorpt_correction_T_max 0.624 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22244 _diffrn_reflns_av_R_equivalents 0.1302 _diffrn_reflns_av_sigmaI/netI 0.0957 _diffrn_reflns_limit_h_min -47 _diffrn_reflns_limit_h_max 47 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4767 _reflns_number_gt 2122 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4767 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2616 _refine_ls_R_factor_gt 0.1661 _refine_ls_wR_factor_ref 0.4616 _refine_ls_wR_factor_gt 0.3989 _refine_ls_goodness_of_fit_ref 1.401 _refine_ls_restrained_S_all 1.401 _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 0.87001(12) 0.9355(8) 0.7872(3) 0.1038(17) Uani 1 1 d . . . S2 S 0.80403(8) 0.9859(4) 0.55357(15) 0.0459(8) Uani 1 1 d . . . S3 S 0.71651(9) 1.0161(4) 0.38927(15) 0.0540(9) Uani 1 1 d . . . S4 S 0.59743(13) 1.1111(8) 0.2691(2) 0.1126(18) Uani 1 1 d . . . O1 O 0.9329(4) 0.894(3) 0.9374(10) 0.158(6) Uani 1 1 d . . . O2 O 0.7127(2) 0.7435(9) 0.6003(4) 0.0490(19) Uani 1 1 d . . . O3 O 0.7259(2) 0.9801(10) 0.6836(4) 0.050(2) Uani 1 1 d . . . O4 O 0.6576(2) 0.9975(10) 0.5544(4) 0.0490(19) Uani 1 1 d . . . O5 O 0.6978(2) 1.2408(11) 0.5778(4) 0.060(2) Uani 1 1 d . . . N1 N 0.7930(3) 0.9442(14) 0.6677(5) 0.053(3) Uani 1 1 d . . . N2 N 0.6607(3) 1.0453(13) 0.4190(5) 0.056(3) Uani 1 1 d . . . C1 C 0.9409(6) 0.898(4) 0.8802(16) 0.153(10) Uani 1 1 d . . . C2 C 0.9160(4) 0.899(2) 0.8065(9) 0.078(4) Uani 1 1 d . . . C3 C 0.9211(5) 0.887(3) 0.7424(11) 0.111(6) Uani 1 1 d . . . H3 H 0.9452 0.8754 0.7477 0.133 Uiso 1 1 calc R . . C4 C 0.8889(3) 0.8905(19) 0.6647(8) 0.078(5) Uani 1 1 d . . . H4 H 0.8875 0.8762 0.6188 0.093 Uiso 1 1 calc R . . C5 C 0.8585(3) 0.9297(18) 0.6949(7) 0.061(3) Uani 1 1 d . . . C6 C 0.8188(3) 0.9497(17) 0.6465(6) 0.054(3) Uani 1 1 d . . . C7 C 0.7591(3) 0.9620(16) 0.6106(6) 0.050(3) Uani 1 1 d . . . C8 C 0.7596(3) 0.9872(13) 0.5424(6) 0.044(3) Uani 1 1 d . . . C9 C 0.7243(3) 1.0081(13) 0.4772(5) 0.042(3) Uani 1 1 d . . . C10 C 0.6916(3) 1.0271(14) 0.4815(5) 0.047(3) Uani 1 1 d . . . C11 C 0.6913(3) 1.0426(17) 0.5575(6) 0.053(3) Uani 1 1 d . . . C12 C 0.7233(3) 0.9310(16) 0.6142(6) 0.054(3) Uani 1 1 d . . . C13 C 0.6702(4) 1.0401(17) 0.3652(6) 0.064(4) Uani 1 1 d . . . C14 C 0.6432(4) 1.0624(19) 0.2893(7) 0.075(4) Uani 1 1 d . . . C15 C 0.6506(4) 1.0627(18) 0.2255(6) 0.063(4) Uani 1 1 d . . . H15 H 0.6735 1.0477 0.2253 0.076 Uiso 1 1 calc R . . C16 C 0.6161(7) 1.090(3) 0.1649(12) 0.122(7) Uani 1 1 d . . . H16 H 0.6138 1.0879 0.1181 0.146 Uiso 1 1 calc R . . C17 C 0.5866(6) 1.120(3) 0.1775(9) 0.111(7) Uani 1 1 d . . . H17 H 0.5629 1.1423 0.1412 0.134 Uiso 1 1 calc R . . C18 C 0.7104(3) 0.6720(17) 0.6643(6) 0.057(3) Uani 1 1 d . . . H18A H 0.6850 0.6731 0.6579 0.069 Uiso 1 1 calc R . . H18B H 0.7200 0.5477 0.6751 0.069 Uiso 1 1 calc R . . C19 C 0.7335(3) 0.7993(17) 0.7212(6) 0.056(3) Uani 1 1 d . . . H19A H 0.7596 0.7671 0.7403 0.068 Uiso 1 1 calc R . . H19B H 0.7265 0.8005 0.7605 0.068 Uiso 1 1 calc R . . C20 C 0.6366(4) 1.1547(19) 0.5400(8) 0.078(4) Uani 1 1 d . . . H20A H 0.6188 1.1462 0.5597 0.094 Uiso 1 1 calc R . . H20B H 0.6233 1.1753 0.4883 0.094 Uiso 1 1 calc R . . C21 C 0.6630(5) 1.302(2) 0.5747(10) 0.098(5) Uani 1 1 d . . . H21A H 0.6549 1.4149 0.5468 0.118 Uiso 1 1 calc R . . H21B H 0.6656 1.3251 0.6230 0.118 Uiso 1 1 calc R . . C22 C 0.9846(4) 0.869(3) 0.9035(16) 0.288(11) Uani 1 1 d G . . C23 C 1.0047(5) 1.009(2) 0.8916(17) 0.288(11) Uani 1 1 d G . . C24 C 1.0422(5) 0.985(3) 0.9106(17) 0.288(11) Uani 1 1 d G . . C25 C 1.0596(4) 0.820(3) 0.9414(16) 0.288(11) Uani 1 1 d G . . C26 C 1.0395(5) 0.680(2) 0.9533(16) 0.288(11) Uani 1 1 d G . . C27 C 1.0020(5) 0.704(3) 0.9343(16) 0.288(11) Uani 1 1 d G . . F1 F 0.9883(5) 1.160(3) 0.8569(13) 0.298(6) Uani 1 1 d . . . F2 F 1.0617(5) 1.127(3) 0.9079(14) 0.298(6) Uani 1 1 d . . . F3 F 1.0958(5) 0.816(3) 0.9775(14) 0.298(6) Uani 1 1 d . . . F4 F 1.0537(5) 0.531(3) 0.9863(15) 0.298(6) Uani 1 1 d . . . F5 F 0.9807(5) 0.553(3) 0.9608(15) 0.298(6) 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 0.071(3) 0.143(4) 0.080(3) -0.005(3) 0.018(2) -0.022(3) S2 0.0566(17) 0.0413(17) 0.0419(16) 0.0006(12) 0.0238(13) -0.0016(13) S3 0.070(2) 0.054(2) 0.0326(15) 0.0014(13) 0.0181(14) 0.0036(15) S4 0.091(3) 0.137(5) 0.075(3) -0.004(3) 0.006(2) 0.002(3) O1 0.098(10) 0.189(16) 0.168(16) -0.003(13) 0.042(10) -0.043(10) O2 0.072(5) 0.031(4) 0.045(4) -0.006(3) 0.027(4) -0.016(4) O3 0.050(4) 0.063(5) 0.027(4) -0.007(3) 0.009(3) -0.011(4) O4 0.044(4) 0.052(5) 0.044(4) -0.001(4) 0.013(3) 0.002(4) O5 0.088(6) 0.039(5) 0.058(5) 0.002(4) 0.037(5) 0.011(4) N1 0.043(5) 0.072(7) 0.043(5) 0.000(5) 0.018(5) 0.000(5) N2 0.060(6) 0.045(6) 0.045(6) -0.005(4) 0.007(5) -0.001(5) C1 0.098(16) 0.21(3) 0.14(2) -0.04(2) 0.048(16) -0.066(17) C2 0.042(7) 0.079(11) 0.092(12) 0.000(8) 0.011(8) -0.015(7) C3 0.102(14) 0.102(15) 0.130(17) 0.019(12) 0.054(13) 0.006(11) C4 0.012(5) 0.076(10) 0.101(11) 0.011(8) -0.015(6) 0.010(6) C5 0.055(8) 0.062(8) 0.063(8) -0.001(7) 0.024(6) -0.004(6) C6 0.063(8) 0.051(8) 0.050(7) -0.010(6) 0.026(6) -0.012(6) C7 0.043(6) 0.057(8) 0.046(7) -0.012(5) 0.017(5) -0.016(5) C8 0.061(7) 0.021(6) 0.040(6) 0.004(4) 0.013(5) 0.003(5) C9 0.059(7) 0.027(6) 0.033(6) -0.007(4) 0.013(5) -0.002(5) C10 0.056(7) 0.041(7) 0.031(6) 0.000(5) 0.008(5) -0.007(5) C11 0.060(8) 0.060(8) 0.034(6) -0.001(5) 0.015(5) 0.000(6) C12 0.065(8) 0.044(7) 0.040(7) -0.009(5) 0.011(6) -0.008(6) C13 0.102(11) 0.049(8) 0.036(7) -0.009(5) 0.027(7) -0.011(7) C14 0.097(11) 0.058(9) 0.043(8) -0.001(6) 0.008(7) 0.005(8) C15 0.083(9) 0.071(9) 0.023(6) -0.006(6) 0.012(6) -0.001(7) C16 0.15(2) 0.118(17) 0.097(15) -0.025(12) 0.058(16) -0.013(16) C17 0.126(16) 0.078(13) 0.069(11) 0.003(9) -0.012(11) -0.003(11) C18 0.061(8) 0.048(8) 0.056(7) 0.009(6) 0.019(6) 0.002(6) C19 0.066(8) 0.063(8) 0.031(6) 0.015(6) 0.013(6) -0.004(6) C20 0.063(9) 0.065(10) 0.079(10) -0.012(8) 0.007(7) 0.007(8) C21 0.116(13) 0.073(11) 0.146(16) -0.014(11) 0.095(13) 0.010(10) C22 0.084(8) 0.152(13) 0.46(2) -0.017(15) -0.028(12) 0.021(6) C23 0.084(8) 0.152(13) 0.46(2) -0.017(15) -0.028(12) 0.021(6) C24 0.084(8) 0.152(13) 0.46(2) -0.017(15) -0.028(12) 0.021(6) C25 0.084(8) 0.152(13) 0.46(2) -0.017(15) -0.028(12) 0.021(6) C26 0.084(8) 0.152(13) 0.46(2) -0.017(15) -0.028(12) 0.021(6) C27 0.084(8) 0.152(13) 0.46(2) -0.017(15) -0.028(12) 0.021(6) F1 0.135(6) 0.290(12) 0.374(14) 0.036(10) 0.028(7) 0.028(6) F2 0.135(6) 0.290(12) 0.374(14) 0.036(10) 0.028(7) 0.028(6) F3 0.135(6) 0.290(12) 0.374(14) 0.036(10) 0.028(7) 0.028(6) F4 0.135(6) 0.290(12) 0.374(14) 0.036(10) 0.028(7) 0.028(6) F5 0.135(6) 0.290(12) 0.374(14) 0.036(10) 0.028(7) 0.028(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 C2 1.731(14) . ? S1 C5 1.752(14) . ? S2 C8 1.698(12) . ? S2 C6 1.759(12) . ? S3 C9 1.701(10) . ? S3 C13 1.711(15) . ? S4 C14 1.735(16) . ? S4 C17 1.74(2) . ? O1 C1 1.36(3) . ? O2 C12 1.419(13) . ? O2 C18 1.463(12) . ? O3 C12 1.435(13) . ? O3 C19 1.489(13) . ? O4 C11 1.369(14) . ? O4 C20 1.374(14) . ? O5 C21 1.441(16) . ? O5 C11 1.491(14) . ? N1 C6 1.294(14) . ? N1 C7 1.355(14) . ? N2 C13 1.325(16) . ? N2 C10 1.342(14) . ? C1 C2 1.40(3) . ? C1 C22 1.62(3) . ? C2 C3 1.43(2) . ? C3 C4 1.55(2) . ? C3 H3 0.9300 . ? C4 C5 1.626(19) . ? C4 H4 0.9300 . ? C5 C6 1.464(17) . ? C7 C8 1.428(16) . ? C7 C12 1.493(16) . ? C8 C9 1.466(15) . ? C9 C10 1.366(16) . ? C10 C11 1.579(16) . ? C11 C12 1.531(16) . ? C13 C14 1.465(18) . ? C14 C15 1.472(19) . ? C15 C16 1.41(3) . ? C15 H15 0.9300 . ? C16 C17 1.34(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.460(16) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.46(2) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.3900 . ? C22 C27 1.3900 . ? C23 F1 1.32(2) . ? C23 C24 1.3900 . ? C24 F2 1.31(3) . ? C24 C25 1.3900 . ? C25 F3 1.31(2) . ? C25 C26 1.3900 . ? C26 F4 1.27(2) . ? C26 C27 1.3900 . ? C27 F5 1.63(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 C5 89.1(8) . . ? C8 S2 C6 88.5(6) . . ? C9 S3 C13 88.5(6) . . ? C14 S4 C17 89.6(9) . . ? C12 O2 C18 107.0(8) . . ? C12 O3 C19 102.1(8) . . ? C11 O4 C20 108.1(10) . . ? C21 O5 C11 104.2(10) . . ? C6 N1 C7 110.6(10) . . ? C13 N2 C10 108.5(11) . . ? O1 C1 C2 128(2) . . ? O1 C1 C22 113(2) . . ? C2 C1 C22 119(2) . . ? C1 C2 C3 132.6(17) . . ? C1 C2 S1 115.1(16) . . ? C3 C2 S1 112.1(13) . . ? C2 C3 C4 124.0(16) . . ? C2 C3 H3 118.0 . . ? C4 C3 H3 118.0 . . ? C3 C4 C5 91.8(13) . . ? C3 C4 H4 134.1 . . ? C5 C4 H4 134.1 . . ? C6 C5 C4 122.2(11) . . ? C6 C5 S1 114.9(10) . . ? C4 C5 S1 122.8(9) . . ? N1 C6 C5 124.1(11) . . ? N1 C6 S2 116.1(9) . . ? C5 C6 S2 119.8(10) . . ? N1 C7 C8 114.9(10) . . ? N1 C7 C12 124.2(10) . . ? C8 C7 C12 120.3(10) . . ? C7 C8 C9 119.2(11) . . ? C7 C8 S2 109.9(8) . . ? C9 C8 S2 131.0(9) . . ? C10 C9 C8 121.2(10) . . ? C10 C9 S3 109.9(8) . . ? C8 C9 S3 128.9(9) . . ? N2 C10 C9 116.9(10) . . ? N2 C10 C11 122.6(11) . . ? C9 C10 C11 120.3(9) . . ? O4 C11 O5 106.9(9) . . ? O4 C11 C12 112.8(10) . . ? O5 C11 C12 108.4(9) . . ? O4 C11 C10 112.4(9) . . ? O5 C11 C10 105.7(9) . . ? C12 C11 C10 110.3(10) . . ? O2 C12 O3 108.9(9) . . ? O2 C12 C7 110.1(10) . . ? O3 C12 C7 111.7(9) . . ? O2 C12 C11 106.3(9) . . ? O3 C12 C11 107.1(9) . . ? C7 C12 C11 112.5(10) . . ? N2 C13 C14 122.9(14) . . ? N2 C13 S3 116.1(10) . . ? C14 C13 S3 120.9(11) . . ? C13 C14 C15 127.6(14) . . ? C13 C14 S4 118.7(11) . . ? C15 C14 S4 113.5(10) . . ? C16 C15 C14 106.5(14) . . ? C16 C15 H15 126.8 . . ? C14 C15 H15 126.8 . . ? C17 C16 C15 117.2(19) . . ? C17 C16 H16 121.4 . . ? C15 C16 H16 121.4 . . ? C16 C17 S4 113.0(15) . . ? C16 C17 H17 123.5 . . ? S4 C17 H17 123.5 . . ? C19 C18 O2 103.2(9) . . ? C19 C18 H18A 111.1 . . ? O2 C18 H18A 111.1 . . ? C19 C18 H18B 111.1 . . ? O2 C18 H18B 111.1 . . ? H18A C18 H18B 109.1 . . ? C18 C19 O3 103.3(8) . . ? C18 C19 H19A 111.1 . . ? O3 C19 H19A 111.1 . . ? C18 C19 H19B 111.1 . . ? O3 C19 H19B 111.1 . . ? H19A C19 H19B 109.1 . . ? O4 C20 C21 105.3(11) . . ? O4 C20 H20A 110.7 . . ? C21 C20 H20A 110.7 . . ? O4 C20 H20B 110.7 . . ? C21 C20 H20B 110.7 . . ? H20A C20 H20B 108.8 . . ? O5 C21 C20 105.8(11) . . ? O5 C21 H21A 110.6 . . ? C20 C21 H21A 110.6 . . ? O5 C21 H21B 110.6 . . ? C20 C21 H21B 110.6 . . ? H21A C21 H21B 108.7 . . ? C23 C22 C27 120.0 . . ? C23 C22 C1 119.5(18) . . ? C27 C22 C1 120.5(18) . . ? F1 C23 C22 121.2(18) . . ? F1 C23 C24 118.6(19) . . ? C22 C23 C24 120.0 . . ? F2 C24 C25 120.6(17) . . ? F2 C24 C23 118.8(18) . . ? C25 C24 C23 120.0 . . ? F3 C25 C26 118.0(19) . . ? F3 C25 C24 119.2(18) . . ? C26 C25 C24 120.0 . . ? F4 C26 C25 124.1(19) . . ? F4 C26 C27 116(2) . . ? C25 C26 C27 120.0 . . ? C26 C27 C22 120.0 . . ? C26 C27 F5 119.0(15) . . ? C22 C27 F5 120.2(16) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.434 _refine_diff_density_min -0.889 _refine_diff_density_rms 0.235 data_paul86 _database_code_depnum_ccdc_archive 'CCDC 914103' #TrackingRef '30a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-Bis-(thiophen-2-yl)-3,5-di-n-hexyl-4H-cyclopenta[1,2-b:5,4-b']dithiophen-4-one ; _chemical_name_common ; 2,6-Bis-(thiophen-2-yl)-3,5-di-n-hexyl-4H-cyclopenta[1,2-b:5,4-b']dithiophen-4-one ; _chemical_melting_point ? _chemical_formula_moiety 'C29 H32 O S4' _chemical_formula_sum 'C29 H32 O S4' _chemical_formula_weight 524.79 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(1)/c _symmetry_space_group_name_Hall -P2ybc 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 5.3435(4) _cell_length_b 20.1523(15) _cell_length_c 24.6864(18) _cell_angle_alpha 90.00 _cell_angle_beta 92.0210(10) _cell_angle_gamma 90.00 _cell_volume 2656.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3626 _cell_measurement_theta_min 2.6101 _cell_measurement_theta_max 23.4542 _exptl_crystal_description plate _exptl_crystal_colour pink _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.379 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8942 _exptl_absorpt_correction_T_max 0.9628 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 30649 _diffrn_reflns_av_R_equivalents 0.0700 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5241 _reflns_number_gt 3974 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0189P)^2^+5.5521P] 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 5241 _refine_ls_number_parameters 311 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0775 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1300 _refine_ls_wR_factor_gt 0.1169 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.002 _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 0.05875(13) 0.49891(4) 0.41373(3) 0.01847(18) Uani 1 1 d . . . S2 S 0.55931(14) 0.60209(4) 0.32976(3) 0.02170(19) Uani 1 1 d . . . S4 S -0.09497(16) 0.32600(4) 0.50177(4) 0.0302(2) Uani 1 1 d . . . O1 O 0.5479(4) 0.36065(11) 0.28829(9) 0.0276(5) Uani 1 1 d . . . C1 C -0.0050(5) 0.41377(15) 0.41777(12) 0.0190(6) Uani 1 1 d . . . C2 C 0.1304(5) 0.37716(15) 0.38167(12) 0.0189(6) Uani 1 1 d . . . C3 C 0.2870(5) 0.41949(15) 0.35180(12) 0.0190(6) Uani 1 1 d . . . C4 C 0.2696(5) 0.48552(15) 0.36467(12) 0.0193(6) Uani 1 1 d . . . C5 C 0.4524(5) 0.52319(15) 0.33428(12) 0.0196(6) Uani 1 1 d . . . C6 C 0.5826(5) 0.48022(15) 0.30254(12) 0.0199(6) Uani 1 1 d . . . C7 C 0.4840(5) 0.41137(15) 0.31045(12) 0.0208(6) Uani 1 1 d . . . C8 C 0.7762(6) 0.51036(16) 0.27355(12) 0.0220(7) Uani 1 1 d . . . C9 C 0.7873(6) 0.57777(16) 0.28438(12) 0.0218(7) Uani 1 1 d . A . C10 C 0.9559(6) 0.62926(16) 0.26599(13) 0.0252(7) Uani 1 1 d . . . S3 S 1.1545(3) 0.61997(9) 0.21174(6) 0.0312(4) Uani 0.695(4) 1 d P A 1 C11 C 0.9848(16) 0.6941(6) 0.2856(3) 0.0333(8) Uani 0.695(4) 1 d P A 1 H11 H 0.8906 0.7125 0.3138 0.040 Uiso 0.695(4) 1 calc PR A 1 C12 C 1.1796(18) 0.7300(6) 0.2568(3) 0.0333(8) Uani 0.695(4) 1 d P A 1 H12 H 1.2373 0.7736 0.2648 0.040 Uiso 0.695(4) 1 calc PR A 1 C13 C 1.2599(17) 0.6919(3) 0.2181(4) 0.0333(8) Uani 0.695(4) 1 d P A 1 H13 H 1.3815 0.7078 0.1942 0.040 Uiso 0.695(4) 1 calc PR A 1 S3A S 0.9946(9) 0.6984(3) 0.30373(14) 0.0333(8) Uani 0.305(4) 1 d P A 2 C11A C 1.091(3) 0.6300(10) 0.2202(8) 0.0333(8) Uani 0.305(4) 1 d P A 2 H11A H 1.0906 0.5967 0.1929 0.040 Uiso 0.305(4) 1 calc PR A 2 C13A C 1.174(4) 0.7335(14) 0.2684(7) 0.0333(8) Uani 0.305(4) 1 d PD A 2 H13A H 1.2264 0.7769 0.2786 0.040 Uiso 0.305(4) 1 calc PR A 2 C12A C 1.270(4) 0.7060(7) 0.2208(10) 0.0333(8) Uani 0.305(4) 1 d PD A 2 H12A H 1.3909 0.7222 0.1968 0.040 Uiso 0.305(4) 1 calc PR A 2 C14 C -0.1703(5) 0.39214(15) 0.46024(12) 0.0198(6) Uani 1 1 d . . . C15 C -0.3943(5) 0.42418(13) 0.47692(10) 0.0113(5) Uani 1 1 d . . . H15 H -0.4712 0.4614 0.4595 0.014 Uiso 1 1 calc R . . C16 C -0.4836(6) 0.39154(17) 0.52366(13) 0.0281(7) Uani 1 1 d . . . H16 H -0.6294 0.4057 0.5413 0.034 Uiso 1 1 calc R . . C17 C -0.3455(6) 0.33903(17) 0.54091(14) 0.0298(8) Uani 1 1 d . . . H17 H -0.3838 0.3125 0.5713 0.036 Uiso 1 1 calc R . . C18 C 0.9421(6) 0.47255(17) 0.23651(12) 0.0255(7) Uani 1 1 d . . . H18A H 0.9658 0.4269 0.2505 0.031 Uiso 1 1 calc R . . H18B H 1.1084 0.4942 0.2362 0.031 Uiso 1 1 calc R . . C19 C 0.8309(7) 0.4695(2) 0.17842(13) 0.0369(9) Uani 1 1 d . . . H19A H 0.6777 0.4419 0.1780 0.044 Uiso 1 1 calc R . . H19B H 0.7820 0.5148 0.1667 0.044 Uiso 1 1 calc R . . C20 C 1.0125(9) 0.4409(3) 0.13817(16) 0.0625(14) Uani 1 1 d . A . H20A H 0.9307 0.4417 0.1016 0.075 Uiso 1 1 calc R . . H20B H 1.1612 0.4701 0.1374 0.075 Uiso 1 1 calc R . . C21 C 1.0990(14) 0.3713(3) 0.1502(3) 0.106(2) Uani 1 1 d . . . H21A H 0.9623 0.3381 0.1492 0.127 Uiso 0.695(4) 1 calc PR A 1 H21B H 1.2038 0.3672 0.1839 0.127 Uiso 0.695(4) 1 calc PR A 1 H21C H 0.9498 0.3422 0.1476 0.127 Uiso 0.305(4) 1 calc PR A 2 H21D H 1.1611 0.3702 0.1884 0.127 Uiso 0.305(4) 1 calc PR A 2 C22 C 1.270(5) 0.3733(11) 0.0916(10) 0.0922(19) Uani 0.305(4) 1 d P A 1 H22A H 1.1601 0.3790 0.0587 0.111 Uiso 0.305(4) 1 calc PR A 1 H22B H 1.3985 0.4086 0.0930 0.111 Uiso 0.305(4) 1 calc PR A 1 C23 C 1.387(5) 0.3031(10) 0.0947(10) 0.0922(19) Uani 0.305(4) 1 d P A 1 H23A H 1.5070 0.3008 0.1256 0.138 Uiso 0.305(4) 1 calc PR A 1 H23B H 1.4743 0.2941 0.0612 0.138 Uiso 0.305(4) 1 calc PR A 1 H23C H 1.2552 0.2700 0.0991 0.138 Uiso 0.305(4) 1 calc PR A 1 C22B C 1.321(2) 0.3364(5) 0.1124(4) 0.0922(19) Uani 0.695(4) 1 d P A 2 H22C H 1.4495 0.3691 0.1023 0.111 Uiso 0.695(4) 1 calc PR A 2 H22D H 1.4034 0.2985 0.1314 0.111 Uiso 0.695(4) 1 calc PR A 2 C23B C 1.1810(19) 0.3163(4) 0.0689(4) 0.0922(19) Uani 0.695(4) 1 d P A 2 H23D H 1.0292 0.2944 0.0811 0.138 Uiso 0.695(4) 1 calc PR A 2 H23E H 1.2776 0.2851 0.0476 0.138 Uiso 0.695(4) 1 calc PR A 2 H23F H 1.1346 0.3548 0.0466 0.138 Uiso 0.695(4) 1 calc PR A 2 C24 C 0.1229(6) 0.30296(14) 0.37598(12) 0.0209(6) Uani 1 1 d . . . H24A H 0.1166 0.2912 0.3370 0.025 Uiso 1 1 calc R . . H24B H -0.0314 0.2859 0.3921 0.025 Uiso 1 1 calc R . . C25 C 0.3512(5) 0.26950(14) 0.40373(12) 0.0203(6) Uani 1 1 d . . . H25A H 0.5029 0.2814 0.3840 0.024 Uiso 1 1 calc R . . H25B H 0.3725 0.2867 0.4412 0.024 Uiso 1 1 calc R . . C26 C 0.3283(6) 0.19452(15) 0.40574(13) 0.0232(7) Uani 1 1 d . . . H26A H 0.3020 0.1774 0.3684 0.028 Uiso 1 1 calc R . . H26B H 0.1791 0.1827 0.4264 0.028 Uiso 1 1 calc R . . C27 C 0.5584(6) 0.16071(15) 0.43196(13) 0.0232(7) Uani 1 1 d . . . H27A H 0.7062 0.1713 0.4105 0.028 Uiso 1 1 calc R . . H27B H 0.5883 0.1792 0.4688 0.028 Uiso 1 1 calc R . . C28 C 0.5347(6) 0.08595(16) 0.43625(15) 0.0302(8) Uani 1 1 d . . . H28A H 0.5235 0.0668 0.3993 0.036 Uiso 1 1 calc R . . H28B H 0.3775 0.0751 0.4544 0.036 Uiso 1 1 calc R . . C29 C 0.7533(7) 0.05408(18) 0.46764(16) 0.0378(9) Uani 1 1 d . . . H29A H 0.9097 0.0644 0.4499 0.057 Uiso 1 1 calc R . . H29B H 0.7297 0.0059 0.4685 0.057 Uiso 1 1 calc R . . H29C H 0.7613 0.0714 0.5048 0.057 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 0.0160(4) 0.0184(4) 0.0211(4) -0.0015(3) 0.0012(3) 0.0025(3) S2 0.0206(4) 0.0197(4) 0.0249(4) 0.0034(3) 0.0028(3) 0.0025(3) S4 0.0239(4) 0.0309(5) 0.0361(5) 0.0047(4) 0.0059(3) 0.0024(3) O1 0.0310(13) 0.0236(12) 0.0286(12) -0.0072(10) 0.0078(10) 0.0029(10) C1 0.0135(14) 0.0202(16) 0.0230(15) -0.0014(12) -0.0041(12) 0.0004(11) C2 0.0150(14) 0.0202(16) 0.0212(15) -0.0011(12) -0.0026(11) 0.0009(12) C3 0.0171(14) 0.0197(15) 0.0202(15) -0.0012(12) -0.0019(12) 0.0029(12) C4 0.0160(14) 0.0208(16) 0.0210(15) 0.0000(12) -0.0007(12) 0.0029(12) C5 0.0173(15) 0.0210(15) 0.0204(15) 0.0019(12) -0.0009(12) 0.0022(12) C6 0.0177(15) 0.0237(16) 0.0185(15) 0.0000(12) 0.0002(12) 0.0026(12) C7 0.0191(15) 0.0242(17) 0.0188(15) -0.0003(13) -0.0023(12) 0.0032(12) C8 0.0195(15) 0.0275(18) 0.0187(15) 0.0031(13) -0.0025(12) 0.0039(13) C9 0.0187(15) 0.0267(17) 0.0199(15) 0.0047(13) 0.0012(12) 0.0035(13) C10 0.0200(15) 0.0299(18) 0.0256(17) 0.0093(14) 0.0014(13) 0.0031(13) S3 0.0267(9) 0.0469(10) 0.0204(7) 0.0064(6) 0.0048(5) -0.0082(7) C11 0.0322(9) 0.0326(13) 0.0355(18) 0.012(2) 0.0050(13) -0.0016(8) C12 0.0322(9) 0.0326(13) 0.0355(18) 0.012(2) 0.0050(13) -0.0016(8) C13 0.0322(9) 0.0326(13) 0.0355(18) 0.012(2) 0.0050(13) -0.0016(8) S3A 0.0322(9) 0.0326(13) 0.0355(18) 0.012(2) 0.0050(13) -0.0016(8) C11A 0.0322(9) 0.0326(13) 0.0355(18) 0.012(2) 0.0050(13) -0.0016(8) C13A 0.0322(9) 0.0326(13) 0.0355(18) 0.012(2) 0.0050(13) -0.0016(8) C12A 0.0322(9) 0.0326(13) 0.0355(18) 0.012(2) 0.0050(13) -0.0016(8) C14 0.0169(15) 0.0201(15) 0.0223(16) -0.0035(12) -0.0009(12) -0.0022(12) C15 0.0101(13) 0.0127(13) 0.0110(13) -0.0067(10) 0.0004(10) -0.0043(10) C16 0.0186(16) 0.0341(19) 0.0318(18) -0.0150(15) 0.0047(13) -0.0039(14) C17 0.0319(19) 0.0299(19) 0.0277(18) -0.0009(14) 0.0029(14) -0.0098(15) C18 0.0247(17) 0.0301(18) 0.0219(16) -0.0003(14) 0.0041(13) 0.0022(14) C19 0.040(2) 0.050(2) 0.0214(17) -0.0024(16) 0.0016(15) -0.0051(18) C20 0.067(3) 0.098(4) 0.024(2) -0.017(2) 0.018(2) -0.025(3) C21 0.127(6) 0.086(5) 0.107(5) -0.047(4) 0.062(4) 0.017(4) C22 0.107(5) 0.066(4) 0.102(5) -0.021(3) -0.014(4) 0.006(4) C23 0.107(5) 0.066(4) 0.102(5) -0.021(3) -0.014(4) 0.006(4) C22B 0.107(5) 0.066(4) 0.102(5) -0.021(3) -0.014(4) 0.006(4) C23B 0.107(5) 0.066(4) 0.102(5) -0.021(3) -0.014(4) 0.006(4) C24 0.0193(15) 0.0189(15) 0.0247(16) -0.0026(13) 0.0015(12) -0.0004(12) C25 0.0173(15) 0.0204(16) 0.0232(16) -0.0018(12) -0.0002(12) -0.0010(12) C26 0.0172(15) 0.0220(16) 0.0305(17) 0.0004(13) -0.0007(13) -0.0011(12) C27 0.0190(15) 0.0218(16) 0.0288(17) -0.0012(13) -0.0002(13) -0.0004(12) C28 0.0247(17) 0.0237(18) 0.042(2) 0.0064(15) 0.0003(15) 0.0005(14) C29 0.032(2) 0.033(2) 0.048(2) 0.0135(17) -0.0059(17) 0.0043(16) _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 1.704(3) . ? S1 C1 1.753(3) . ? S2 C5 1.694(3) . ? S2 C9 1.754(3) . ? S4 C17 1.699(3) . ? S4 C14 1.721(3) . ? O1 C7 1.214(4) . ? C1 C2 1.381(4) . ? C1 C14 1.461(4) . ? C2 C3 1.420(4) . ? C2 C24 1.502(4) . ? C3 C4 1.372(4) . ? C3 C7 1.501(4) . ? C4 C5 1.465(4) . ? C5 C6 1.373(4) . ? C6 C8 1.415(4) . ? C6 C7 1.500(4) . ? C8 C9 1.386(4) . ? C8 C18 1.503(4) . ? C9 C10 1.457(4) . ? C10 C11A 1.363(18) . ? C10 C11 1.399(12) . ? C10 S3A 1.684(7) . ? C10 S3 1.748(3) . ? S3 C13 1.560(6) . ? C11 C12 1.472(10) . ? C11 H11 0.9500 . ? C12 C13 1.309(9) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? S3A C13A 1.497(19) . ? C11A C12A 1.81(3) . ? C11A H11A 0.9500 . ? C13A C12A 1.413(16) . ? C13A H13A 0.9500 . ? C12A H12A 0.9500 . ? C14 C15 1.433(4) . ? C15 C16 1.425(4) . ? C15 H15 0.9500 . ? C16 C17 1.351(5) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.534(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.526(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.504(8) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22B 1.687(11) . ? C21 C22 1.74(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 H21C 0.9900 . ? C21 H21D 0.9900 . ? C22 C23 1.55(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C22B C23B 1.349(12) . ? C22B H22C 0.9900 . ? C22B H22D 0.9900 . ? C23B H23D 0.9800 . ? C23B H23E 0.9800 . ? C23B H23F 0.9800 . ? C24 C25 1.534(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.517(4) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.529(4) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.516(4) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.521(4) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? 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 91.16(14) . . ? C5 S2 C9 91.33(15) . . ? C17 S4 C14 92.68(16) . . ? C2 C1 C14 130.3(3) . . ? C2 C1 S1 112.3(2) . . ? C14 C1 S1 117.2(2) . . ? C1 C2 C3 110.3(3) . . ? C1 C2 C24 125.4(3) . . ? C3 C2 C24 124.3(3) . . ? C4 C3 C2 114.6(3) . . ? C4 C3 C7 108.6(3) . . ? C2 C3 C7 136.7(3) . . ? C3 C4 C5 109.4(3) . . ? C3 C4 S1 111.7(2) . . ? C5 C4 S1 138.7(2) . . ? C6 C5 C4 109.0(3) . . ? C6 C5 S2 112.0(2) . . ? C4 C5 S2 138.8(2) . . ? C5 C6 C8 114.3(3) . . ? C5 C6 C7 108.8(3) . . ? C8 C6 C7 136.8(3) . . ? O1 C7 C6 127.9(3) . . ? O1 C7 C3 127.8(3) . . ? C6 C7 C3 104.2(2) . . ? C9 C8 C6 110.5(3) . . ? C9 C8 C18 126.3(3) . . ? C6 C8 C18 123.2(3) . . ? C8 C9 C10 131.4(3) . . ? C8 C9 S2 111.8(2) . . ? C10 C9 S2 116.8(2) . . ? C11A C10 C11 102.8(9) . . ? C11A C10 C9 128.1(9) . . ? C11 C10 C9 128.2(4) . . ? C11A C10 S3A 113.1(9) . . ? C11 C10 S3A 13.4(4) . . ? C9 C10 S3A 118.8(3) . . ? C11A C10 S3 8.8(8) . . ? C11 C10 S3 107.6(4) . . ? C9 C10 S3 124.1(3) . . ? S3A C10 S3 116.5(2) . . ? C13 S3 C10 92.8(4) . . ? C10 C11 C12 111.3(6) . . ? C10 C11 H11 124.3 . . ? C12 C11 H11 124.3 . . ? C13 C12 C11 108.5(8) . . ? C13 C12 H12 125.7 . . ? C11 C12 H12 125.7 . . ? C12 C13 S3 119.5(8) . . ? C12 C13 H13 120.2 . . ? S3 C13 H13 120.2 . . ? C13A S3A C10 97.9(10) . . ? C10 C11A C12A 107.3(13) . . ? C10 C11A H11A 126.3 . . ? C12A C11A H11A 126.3 . . ? C12A C13A S3A 124(2) . . ? C12A C13A H13A 118.0 . . ? S3A C13A H13A 118.0 . . ? C13A C12A C11A 97.6(18) . . ? C13A C12A H12A 131.2 . . ? C11A C12A H12A 131.2 . . ? C15 C14 C1 127.1(3) . . ? C15 C14 S4 111.0(2) . . ? C1 C14 S4 121.6(2) . . ? C16 C15 C14 109.4(3) . . ? C16 C15 H15 125.3 . . ? C14 C15 H15 125.3 . . ? C17 C16 C15 115.0(3) . . ? C17 C16 H16 122.5 . . ? C15 C16 H16 122.5 . . ? C16 C17 S4 112.0(3) . . ? C16 C17 H17 124.0 . . ? S4 C17 H17 124.0 . . ? C8 C18 C19 111.8(3) . . ? C8 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? C8 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 . . ? H18A C18 H18B 107.9 . . ? C20 C19 C18 112.9(3) . . ? C20 C19 H19A 109.0 . . ? C18 C19 H19A 109.0 . . ? C20 C19 H19B 109.0 . . ? C18 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C21 C20 C19 115.0(4) . . ? C21 C20 H20A 108.5 . . ? C19 C20 H20A 108.5 . . ? C21 C20 H20B 108.5 . . ? C19 C20 H20B 108.5 . . ? H20A C20 H20B 107.5 . . ? C20 C21 C22B 119.8(6) . . ? C20 C21 C22 88.9(8) . . ? C22B C21 C22 31.8(7) . . ? C20 C21 H21A 113.8 . . ? C22B C21 H21A 103.8 . . ? C22 C21 H21A 113.8 . . ? C20 C21 H21B 113.8 . . ? C22B C21 H21B 92.4 . . ? C22 C21 H21B 113.8 . . ? H21A C21 H21B 111.1 . . ? C20 C21 H21C 107.4 . . ? C22B C21 H21C 107.4 . . ? C22 C21 H21C 113.9 . . ? H21A C21 H21C 6.5 . . ? H21B C21 H21C 115.8 . . ? C20 C21 H21D 107.4 . . ? C22B C21 H21D 107.4 . . ? C22 C21 H21D 128.8 . . ? H21A C21 H21D 103.4 . . ? H21B C21 H21D 15.3 . . ? H21C C21 H21D 106.9 . . ? C23 C22 C21 99.4(17) . . ? C23 C22 H22A 111.9 . . ? C21 C22 H22A 111.9 . . ? C23 C22 H22B 111.9 . . ? C21 C22 H22B 111.9 . . ? H22A C22 H22B 109.6 . . ? C23B C22B C21 100.5(8) . . ? C23B C22B H22C 111.7 . . ? C21 C22B H22C 111.7 . . ? C23B C22B H22D 111.7 . . ? C21 C22B H22D 111.7 . . ? H22C C22B H22D 109.4 . . ? C22B C23B H23D 109.5 . . ? C22B C23B H23E 109.5 . . ? H23D C23B H23E 109.5 . . ? C22B C23B H23F 109.5 . . ? H23D C23B H23F 109.5 . . ? H23E C23B H23F 109.5 . . ? C2 C24 C25 112.2(2) . . ? C2 C24 H24A 109.2 . . ? C25 C24 H24A 109.2 . . ? C2 C24 H24B 109.2 . . ? C25 C24 H24B 109.2 . . ? H24A C24 H24B 107.9 . . ? C26 C25 C24 112.9(2) . . ? C26 C25 H25A 109.0 . . ? C24 C25 H25A 109.0 . . ? C26 C25 H25B 109.0 . . ? C24 C25 H25B 109.0 . . ? H25A C25 H25B 107.8 . . ? C25 C26 C27 113.1(2) . . ? C25 C26 H26A 109.0 . . ? C27 C26 H26A 109.0 . . ? C25 C26 H26B 109.0 . . ? C27 C26 H26B 109.0 . . ? H26A C26 H26B 107.8 . . ? C28 C27 C26 113.9(3) . . ? C28 C27 H27A 108.8 . . ? C26 C27 H27A 108.8 . . ? C28 C27 H27B 108.8 . . ? C26 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? C27 C28 C29 113.0(3) . . ? C27 C28 H28A 109.0 . . ? C29 C28 H28A 109.0 . . ? C27 C28 H28B 109.0 . . ? C29 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.845 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.073 data_str1 _database_code_depnum_ccdc_archive 'CCDC 914104' #TrackingRef '3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Difluoro-benzo[1,2-b:6,5-b']dithiophene-4,5-dione-4,5-dione ; _chemical_name_common ; 2,7-Difluoro-benzo[1,2-b:6,5-b']dithiophene-4,5-dione-4,5-dione ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H2 F2 O2 S2' _chemical_formula_sum 'C10 H2 F2 O2 S2' _chemical_formula_weight 256.24 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 3.8903(7) _cell_length_b 16.656(3) _cell_length_c 14.363(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.947(3) _cell_angle_gamma 90.00 _cell_volume 925.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.839 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.583 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.337 _exptl_absorpt_correction_T_max 0.654 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11769 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0114 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1821 _reflns_number_gt 1664 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0407P)^2^+0.3083P] 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 1821 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0739 _refine_ls_wR_factor_gt 0.0711 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.25959(10) 0.63051(3) 0.27164(3) 0.03929(13) Uani 1 1 d . . . S2 S 0.12206(11) 0.83129(2) 0.32441(3) 0.04063(14) Uani 1 1 d . . . F1 F 0.4363(3) 0.47852(7) 0.26005(8) 0.0633(3) Uani 1 1 d . . . F2 F 0.0796(3) 0.97709(7) 0.39516(9) 0.0651(3) Uani 1 1 d . . . O1 O 0.9337(4) 0.61876(8) 0.58088(9) 0.0569(4) Uani 1 1 d . . . O2 O 0.7523(4) 0.76943(9) 0.63157(9) 0.0603(4) Uani 1 1 d . . . C1 C 0.4568(4) 0.54357(10) 0.31513(12) 0.0411(4) Uani 1 1 d . . . C2 C 0.6205(4) 0.54877(10) 0.40152(11) 0.0385(4) Uani 1 1 d . . . H2A H 0.7395 0.5071 0.4336 0.046 Uiso 1 1 calc R . . C3 C 0.5847(4) 0.62786(9) 0.43688(11) 0.0337(3) Uani 1 1 d . . . C4 C 0.3962(4) 0.67836(9) 0.37482(10) 0.0321(3) Uani 1 1 d . . . C5 C 0.7366(4) 0.65733(10) 0.52773(11) 0.0371(3) Uani 1 1 d . . . C6 C 0.6482(4) 0.74465(10) 0.55481(11) 0.0393(4) Uani 1 1 d . . . C7 C 0.4476(4) 0.79303(10) 0.48356(11) 0.0365(3) Uani 1 1 d . . . C8 C 0.3314(4) 0.76095(9) 0.39755(11) 0.0331(3) Uani 1 1 d . . . C9 C 0.3658(5) 0.87595(10) 0.49201(13) 0.0444(4) Uani 1 1 d . . . H9A H 0.4226 0.9072 0.5451 0.053 Uiso 1 1 calc R . . C10 C 0.1954(5) 0.90204(10) 0.41228(13) 0.0460(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0413(2) 0.0434(2) 0.0321(2) -0.00079(15) -0.00114(16) -0.00025(16) S2 0.0418(2) 0.0365(2) 0.0420(2) 0.00700(16) -0.00301(17) 0.00286(16) F1 0.0806(8) 0.0491(6) 0.0578(7) -0.0206(5) -0.0035(6) 0.0061(6) F2 0.0812(8) 0.0354(5) 0.0755(8) 0.0033(5) -0.0066(6) 0.0167(5) O1 0.0681(9) 0.0523(8) 0.0456(7) 0.0010(6) -0.0163(6) 0.0196(7) O2 0.0749(9) 0.0583(8) 0.0430(7) -0.0124(6) -0.0162(6) 0.0132(7) C1 0.0439(9) 0.0375(8) 0.0420(9) -0.0062(7) 0.0057(7) 0.0013(7) C2 0.0398(8) 0.0357(8) 0.0402(9) 0.0013(7) 0.0043(6) 0.0045(7) C3 0.0324(7) 0.0347(8) 0.0342(8) 0.0021(6) 0.0042(6) 0.0012(6) C4 0.0295(7) 0.0363(8) 0.0306(7) 0.0012(6) 0.0032(6) -0.0019(6) C5 0.0364(8) 0.0399(8) 0.0345(8) 0.0032(7) 0.0004(6) 0.0035(7) C6 0.0380(8) 0.0431(9) 0.0360(8) -0.0027(7) -0.0002(6) 0.0020(7) C7 0.0354(8) 0.0360(8) 0.0377(8) -0.0004(6) 0.0021(6) 0.0019(6) C8 0.0295(7) 0.0343(7) 0.0356(8) 0.0042(6) 0.0032(6) 0.0001(6) C9 0.0474(9) 0.0373(9) 0.0476(10) -0.0056(7) 0.0003(8) 0.0029(7) C10 0.0478(10) 0.0322(8) 0.0570(11) 0.0021(7) 0.0014(8) 0.0044(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 C4 1.7178(16) . ? S1 C1 1.7252(17) . ? S2 C8 1.7210(15) . ? S2 C10 1.7286(19) . ? F1 C1 1.3390(19) . ? F2 C10 1.343(2) . ? O1 C5 1.209(2) . ? O2 C6 1.207(2) . ? C1 C2 1.337(2) . ? C2 C3 1.424(2) . ? C2 H2A 0.9300 . ? C3 C4 1.380(2) . ? C3 C5 1.461(2) . ? C4 C8 1.442(2) . ? C5 C6 1.553(2) . ? C6 C7 1.463(2) . ? C7 C8 1.379(2) . ? C7 C9 1.425(2) . ? C9 C10 1.335(3) . ? C9 H9A 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 89.48(8) . . ? C8 S2 C10 89.23(8) . . ? C2 C1 F1 126.45(16) . . ? C2 C1 S1 115.64(13) . . ? F1 C1 S1 117.91(13) . . ? C1 C2 C3 109.64(15) . . ? C1 C2 H2A 125.2 . . ? C3 C2 H2A 125.2 . . ? C4 C3 C2 113.49(14) . . ? C4 C3 C5 120.73(14) . . ? C2 C3 C5 125.75(14) . . ? C3 C4 C8 121.93(14) . . ? C3 C4 S1 111.75(12) . . ? C8 C4 S1 126.32(12) . . ? O1 C5 C3 123.84(16) . . ? O1 C5 C6 118.81(15) . . ? C3 C5 C6 117.31(13) . . ? O2 C6 C7 123.69(16) . . ? O2 C6 C5 119.13(15) . . ? C7 C6 C5 117.17(14) . . ? C8 C7 C9 113.35(15) . . ? C8 C7 C6 121.00(14) . . ? C9 C7 C6 125.58(15) . . ? C7 C8 C4 121.59(14) . . ? C7 C8 S2 111.95(12) . . ? C4 C8 S2 126.44(12) . . ? C10 C9 C7 109.74(16) . . ? C10 C9 H9A 125.1 . . ? C7 C9 H9A 125.1 . . ? C9 C10 F2 125.98(17) . . ? C9 C10 S2 115.72(13) . . ? F2 C10 S2 118.30(14) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.301 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.044 data_str2 _database_code_depnum_ccdc_archive 'CCDC 914105' #TrackingRef '3b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Dichloro-benzo[1,2-b:6,5-b']dithiophene-4,5-dione ; _chemical_name_common ; 2,7-Dichloro-benzo[1,2-b:6,5-b']dithiophene-4,5-dione ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H2 Cl2 O2 S2' _chemical_formula_sum 'C10 H2 Cl2 O2 S2' _chemical_formula_weight 289.14 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' Cl Cl 0.1484 0.1585 '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 ' _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.8509(11) _cell_length_b 19.822(5) _cell_length_c 13.742(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.669(6) _cell_angle_gamma 90.00 _cell_volume 1047.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5164 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 31.75 _exptl_crystal_description plates _exptl_crystal_colour red _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.833 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.993 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13327 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2058 _reflns_number_gt 1758 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0841P)^2^+6.9094P] 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 2058 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0904 _refine_ls_R_factor_gt 0.0822 _refine_ls_wR_factor_ref 0.2343 _refine_ls_wR_factor_gt 0.2282 _refine_ls_goodness_of_fit_ref 1.225 _refine_ls_restrained_S_all 1.225 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.4488(7) 0.05851(10) 0.59058(17) 0.0630(7) Uani 1 1 d . . . Cl2 Cl 0.2641(6) 0.53049(9) 0.60924(15) 0.0523(6) Uani 1 1 d . . . S1 S 0.4113(5) 0.20798(8) 0.57539(12) 0.0372(5) Uani 1 1 d . . . S2 S 0.3345(4) 0.38242(8) 0.58141(12) 0.0355(5) Uani 1 1 d . . . O1 O -0.0984(17) 0.2117(3) 0.8986(4) 0.0579(15) Uani 1 1 d . . . O2 O -0.1841(17) 0.3489(3) 0.8988(4) 0.0616(16) Uani 1 1 d . . . C1 C 0.343(2) 0.1346(3) 0.6405(5) 0.0424(16) Uani 1 1 d . . . C2 C 0.2118(19) 0.1456(4) 0.7282(5) 0.0421(16) Uani 1 1 d . . . H13A H 0.1648 0.1116 0.7723 0.051 Uiso 1 1 calc R . . C3 C 0.1542(18) 0.2149(3) 0.7452(5) 0.0366(15) Uani 1 1 d . . . C4 C 0.2517(16) 0.2545(3) 0.6685(4) 0.0327(14) Uani 1 1 d . . . C5 C 0.0017(18) 0.2443(4) 0.8307(5) 0.0390(15) Uani 1 1 d . . . C6 C -0.0417(18) 0.3228(4) 0.8318(5) 0.0392(15) Uani 1 1 d . . . C7 C 0.0851(17) 0.3603(3) 0.7493(5) 0.0350(14) Uani 1 1 d . . . C8 C 0.2167(16) 0.3274(3) 0.6707(4) 0.0311(13) Uani 1 1 d . . . C9 C 0.0878(18) 0.4316(4) 0.7386(5) 0.0386(15) Uani 1 1 d . . . H10A H 0.0137 0.4618 0.7851 0.046 Uiso 1 1 calc R . . C10 C 0.2119(19) 0.4498(3) 0.6520(5) 0.0391(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0828(16) 0.0360(10) 0.0715(14) -0.0046(9) 0.0163(11) 0.0085(9) Cl2 0.0687(13) 0.0328(9) 0.0566(11) -0.0010(8) 0.0152(9) -0.0034(8) S1 0.0427(10) 0.0361(9) 0.0330(9) -0.0006(6) 0.0061(7) 0.0029(7) S2 0.0413(9) 0.0333(8) 0.0324(8) 0.0010(6) 0.0087(6) 0.0001(7) O1 0.082(4) 0.056(3) 0.037(3) 0.008(2) 0.015(3) -0.004(3) O2 0.080(4) 0.064(4) 0.043(3) 0.004(3) 0.028(3) 0.019(3) C1 0.049(4) 0.032(3) 0.047(4) 0.002(3) 0.005(3) 0.001(3) C2 0.043(4) 0.040(4) 0.043(4) 0.010(3) 0.004(3) -0.002(3) C3 0.040(4) 0.038(4) 0.032(3) 0.004(3) 0.003(3) 0.001(3) C4 0.030(3) 0.040(3) 0.028(3) 0.002(3) -0.002(2) 0.004(3) C5 0.039(4) 0.051(4) 0.027(3) 0.007(3) 0.002(3) -0.002(3) C6 0.041(4) 0.049(4) 0.029(3) 0.000(3) 0.008(3) 0.003(3) C7 0.036(3) 0.039(3) 0.030(3) 0.002(3) 0.001(3) 0.004(3) C8 0.029(3) 0.035(3) 0.030(3) 0.001(2) 0.004(2) -0.001(2) C9 0.041(4) 0.040(4) 0.035(3) -0.007(3) 0.005(3) 0.002(3) C10 0.046(4) 0.032(3) 0.039(4) -0.003(3) 0.006(3) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.714(7) . ? Cl2 C10 1.718(7) . ? S1 C4 1.714(6) . ? S1 C1 1.734(7) . ? S2 C8 1.719(6) . ? S2 C10 1.730(7) . ? O1 C5 1.214(8) . ? O2 C6 1.210(8) . ? C1 C2 1.346(10) . ? C2 C3 1.414(10) . ? C2 H13A 0.9300 . ? C3 C4 1.380(9) . ? C3 C5 1.458(9) . ? C4 C8 1.450(9) . ? C5 C6 1.564(10) . ? C6 C7 1.458(9) . ? C7 C8 1.378(9) . ? C7 C9 1.422(9) . ? C9 C10 1.351(9) . ? C9 H10A 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 89.9(3) . . ? C8 S2 C10 90.1(3) . . ? C2 C1 Cl1 127.4(6) . . ? C2 C1 S1 113.5(6) . . ? Cl1 C1 S1 119.1(4) . . ? C1 C2 C3 112.0(6) . . ? C1 C2 H13A 124.0 . . ? C3 C2 H13A 124.0 . . ? C4 C3 C2 112.1(6) . . ? C4 C3 C5 121.5(6) . . ? C2 C3 C5 126.4(6) . . ? C3 C4 C8 121.4(6) . . ? C3 C4 S1 112.6(5) . . ? C8 C4 S1 126.0(5) . . ? O1 C5 C3 124.1(7) . . ? O1 C5 C6 119.0(6) . . ? C3 C5 C6 116.9(6) . . ? O2 C6 C7 123.6(7) . . ? O2 C6 C5 119.0(6) . . ? C7 C6 C5 117.3(6) . . ? C8 C7 C9 112.6(6) . . ? C8 C7 C6 121.1(6) . . ? C9 C7 C6 126.3(6) . . ? C7 C8 C4 121.7(6) . . ? C7 C8 S2 112.2(5) . . ? C4 C8 S2 126.1(5) . . ? C10 C9 C7 111.2(6) . . ? C10 C9 H10A 124.4 . . ? C7 C9 H10A 124.4 . . ? C9 C10 Cl2 127.0(6) . . ? C9 C10 S2 113.8(5) . . ? Cl2 C10 S2 119.2(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.527 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.149 data_paul105a _database_code_depnum_ccdc_archive 'CCDC 914106' #TrackingRef '3c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Dibromo-benzo[1,2-b:6,5-b']dithiophene-4,5-dione ; _chemical_name_common ; 2,7-Dibromo-benzo[1,2-b:6,5-b']dithiophene-4,5-dione ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H2 Br2 O2 S2' _chemical_formula_sum 'C10 H2 Br2 O2 S2' _chemical_formula_weight 378.06 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' Br Br -0.2901 2.4595 '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 C2/c _symmetry_space_group_name_Hall -C2yc 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' '-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 21.6810(17) _cell_length_b 5.6778(5) _cell_length_c 17.7679(14) _cell_angle_alpha 90.00 _cell_angle_beta 104.2490(10) _cell_angle_gamma 90.00 _cell_volume 2119.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 8.017 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1417 _exptl_absorpt_correction_T_max 0.5011 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 APEX II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22522 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 34.46 _reflns_number_total 4430 _reflns_number_gt 3958 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT+ ver. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINT+ ver. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL ver. 6.12 (Sheldrick, 2001)' _computing_publication_material 'SHELXTL ver. 6.12 (Sheldrick, 2001)' _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^)+(0.0262P)^2^+2.2482P] 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 4430 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0272 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_ref 0.0559 _refine_ls_wR_factor_gt 0.0537 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.189915(7) 0.54916(3) 0.431262(8) 0.01485(4) Uani 1 1 d . . . Br2 Br -0.012510(7) -0.71221(3) 0.643476(8) 0.01548(4) Uani 1 1 d . . . S1 S 0.126732(17) 0.12514(6) 0.491145(18) 0.01345(6) Uani 1 1 d . . . S2 S 0.051797(17) -0.32323(6) 0.566905(18) 0.01343(6) Uani 1 1 d . . . O1 O 0.22388(5) 0.3360(2) 0.76512(6) 0.0174(2) Uani 1 1 d . . . O2 O 0.15541(6) 0.0081(2) 0.82252(6) 0.0187(2) Uani 1 1 d . . . C1 C 0.17630(7) 0.3673(2) 0.51317(8) 0.0130(2) Uani 1 1 d . . . C2 C 0.19891(7) 0.4019(2) 0.59124(8) 0.0134(2) Uani 1 1 d . . . H2A H 0.2268 0.5260 0.6137 0.016 Uiso 1 1 calc R . . C3 C 0.17518(7) 0.2268(2) 0.63462(7) 0.0122(2) Uani 1 1 d . . . C4 C 0.13498(7) 0.0666(2) 0.58769(7) 0.0121(2) Uani 1 1 d . . . C5 C 0.18816(7) 0.2072(2) 0.71963(8) 0.0129(2) Uani 1 1 d . . . C6 C 0.15215(7) 0.0106(2) 0.75305(8) 0.0134(2) Uani 1 1 d . . . C7 C 0.11367(7) -0.1571(3) 0.69820(7) 0.0127(2) Uani 1 1 d . . . C8 C 0.10498(6) -0.1238(2) 0.61918(7) 0.0122(2) Uani 1 1 d . . . C9 C 0.07768(7) -0.3485(3) 0.71704(8) 0.0142(2) Uani 1 1 d . . . H9A H 0.0782 -0.3965 0.7684 0.017 Uiso 1 1 calc R . . C10 C 0.04246(7) -0.4534(2) 0.65149(8) 0.0138(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01552(7) 0.01594(7) 0.01233(6) 0.00308(4) 0.00194(5) -0.00031(5) Br2 0.01553(7) 0.01747(7) 0.01352(6) -0.00234(4) 0.00374(5) -0.00404(5) S1 0.01485(14) 0.01617(14) 0.00891(12) -0.00074(10) 0.00209(10) -0.00160(12) S2 0.01342(14) 0.01692(14) 0.00935(12) -0.00209(11) 0.00163(10) -0.00255(12) O1 0.0204(5) 0.0169(5) 0.0130(4) -0.0025(4) 0.0005(4) -0.0031(4) O2 0.0235(5) 0.0226(5) 0.0099(4) -0.0029(4) 0.0038(4) -0.0040(4) C1 0.0124(5) 0.0141(5) 0.0124(5) 0.0006(4) 0.0026(4) 0.0005(4) C2 0.0129(5) 0.0135(5) 0.0127(5) 0.0002(4) 0.0010(4) 0.0008(4) C3 0.0125(6) 0.0138(5) 0.0100(5) -0.0003(4) 0.0020(4) 0.0004(4) C4 0.0126(5) 0.0151(5) 0.0087(5) -0.0008(4) 0.0026(4) -0.0002(4) C5 0.0130(6) 0.0140(6) 0.0109(5) -0.0008(4) 0.0018(4) 0.0016(4) C6 0.0133(5) 0.0154(6) 0.0108(5) -0.0016(4) 0.0017(4) 0.0001(5) C7 0.0127(5) 0.0157(6) 0.0092(5) -0.0016(4) 0.0021(4) -0.0011(5) C8 0.0124(5) 0.0145(5) 0.0097(5) -0.0017(4) 0.0026(4) -0.0002(4) C9 0.0143(6) 0.0173(6) 0.0113(5) -0.0006(4) 0.0037(4) -0.0012(5) C10 0.0124(5) 0.0166(6) 0.0125(5) -0.0002(4) 0.0035(4) -0.0007(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.8661(14) . ? Br2 C10 1.8754(14) . ? S1 C4 1.7130(13) . ? S1 C1 1.7297(14) . ? S2 C8 1.7169(14) . ? S2 C10 1.7307(14) . ? O1 C5 1.2164(17) . ? O2 C6 1.2188(16) . ? C1 C2 1.3668(18) . ? C2 C3 1.4291(19) . ? C2 H2A 0.9500 . ? C3 C4 1.3871(19) . ? C3 C5 1.4708(18) . ? C4 C8 1.4433(19) . ? C5 C6 1.561(2) . ? C6 C7 1.4670(19) . ? C7 C8 1.3829(18) . ? C7 C9 1.425(2) . ? C9 C10 1.3625(19) . ? C9 H9A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 S1 C1 91.25(7) . . ? C8 S2 C10 91.06(7) . . ? C2 C1 S1 113.03(11) . . ? C2 C1 Br1 128.76(11) . . ? S1 C1 Br1 118.17(7) . . ? C1 C2 C3 111.15(12) . . ? C1 C2 H2A 124.4 . . ? C3 C2 H2A 124.4 . . ? C4 C3 C2 112.84(12) . . ? C4 C3 C5 120.06(12) . . ? C2 C3 C5 127.09(12) . . ? C3 C4 C8 122.30(12) . . ? C3 C4 S1 111.72(10) . . ? C8 C4 S1 125.98(10) . . ? O1 C5 C3 124.51(13) . . ? O1 C5 C6 118.25(12) . . ? C3 C5 C6 117.22(11) . . ? O2 C6 C7 123.16(13) . . ? O2 C6 C5 118.94(12) . . ? C7 C6 C5 117.85(11) . . ? C8 C7 C9 113.41(12) . . ? C8 C7 C6 119.93(13) . . ? C9 C7 C6 126.41(12) . . ? C7 C8 C4 122.29(12) . . ? C7 C8 S2 111.38(10) . . ? C4 C8 S2 126.23(10) . . ? C10 C9 C7 110.88(12) . . ? C10 C9 H9A 124.6 . . ? C7 C9 H9A 124.6 . . ? C9 C10 S2 113.27(11) . . ? C9 C10 Br2 128.26(11) . . ? S2 C10 Br2 118.47(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 S1 C1 C2 0.53(12) . . . . ? C4 S1 C1 Br1 -177.51(9) . . . . ? S1 C1 C2 C3 -0.14(16) . . . . ? Br1 C1 C2 C3 177.64(11) . . . . ? C1 C2 C3 C4 -0.46(18) . . . . ? C1 C2 C3 C5 -179.17(13) . . . . ? C2 C3 C4 C8 -179.29(13) . . . . ? C5 C3 C4 C8 -0.5(2) . . . . ? C2 C3 C4 S1 0.85(16) . . . . ? C5 C3 C4 S1 179.67(10) . . . . ? C1 S1 C4 C3 -0.78(11) . . . . ? C1 S1 C4 C8 179.37(13) . . . . ? C4 C3 C5 O1 178.15(14) . . . . ? C2 C3 C5 O1 -3.2(2) . . . . ? C4 C3 C5 C6 -3.32(19) . . . . ? C2 C3 C5 C6 175.31(13) . . . . ? O1 C5 C6 O2 7.9(2) . . . . ? C3 C5 C6 O2 -170.75(13) . . . . ? O1 C5 C6 C7 -174.63(13) . . . . ? C3 C5 C6 C7 6.74(18) . . . . ? O2 C6 C7 C8 170.85(14) . . . . ? C5 C6 C7 C8 -6.53(19) . . . . ? O2 C6 C7 C9 -2.9(2) . . . . ? C5 C6 C7 C9 179.70(13) . . . . ? C9 C7 C8 C4 177.38(13) . . . . ? C6 C7 C8 C4 2.8(2) . . . . ? C9 C7 C8 S2 0.92(16) . . . . ? C6 C7 C8 S2 -173.62(11) . . . . ? C3 C4 C8 C7 0.9(2) . . . . ? S1 C4 C8 C7 -179.26(11) . . . . ? C3 C4 C8 S2 176.83(11) . . . . ? S1 C4 C8 S2 -3.34(19) . . . . ? C10 S2 C8 C7 -0.90(11) . . . . ? C10 S2 C8 C4 -177.20(13) . . . . ? C8 C7 C9 C10 -0.41(18) . . . . ? C6 C7 C9 C10 173.71(14) . . . . ? C7 C9 C10 S2 -0.29(16) . . . . ? C7 C9 C10 Br2 179.65(11) . . . . ? C8 S2 C10 C9 0.69(12) . . . . ? C8 S2 C10 Br2 -179.26(9) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 34.46 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.850 _refine_diff_density_min -0.539 _refine_diff_density_rms 0.108 data_paul87 _database_code_depnum_ccdc_archive 'CCDC 914107' #TrackingRef '3d.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Diiodo-benzo[1,2-b:6,5-b']dithiophene-4,5-dione ; _chemical_name_common ; 2,7-Diiodo-benzo[1,2-b:6,5-b']dithiophene-4,5-dione ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H2 I2 O2 S2' _chemical_formula_sum 'C10 H2 I2 O2 S2' _chemical_formula_weight 472.04 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' I I -0.4742 1.8119 '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 12.766(5) _cell_length_b 6.323(2) _cell_length_c 17.766(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.054(5) _cell_angle_gamma 90.00 _cell_volume 1433.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7836 _cell_measurement_theta_min 2.2942 _cell_measurement_theta_max 30.9273 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 4.662 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3352 _exptl_absorpt_correction_T_max 0.6528 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12838 _diffrn_reflns_av_R_equivalents 0.0541 _diffrn_reflns_av_sigmaI/netI 0.0412 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2806 _reflns_number_gt 2509 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0281P)^2^+132.5564P] 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 2806 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0995 _refine_ls_R_factor_gt 0.0938 _refine_ls_wR_factor_ref 0.2127 _refine_ls_wR_factor_gt 0.2105 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.157 _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 I1 I 0.58004(10) 1.43764(19) -0.22518(8) 0.0328(4) Uani 1 1 d . . . I2 I 0.89070(9) 0.18413(17) 0.05481(6) 0.0216(3) Uani 1 1 d . . . S1 S 0.6882(4) 1.0454(7) -0.1254(2) 0.0226(9) Uani 1 1 d . . . S2 S 0.8011(4) 0.6177(6) -0.0289(2) 0.0204(9) Uani 1 1 d . . . O1 O 0.8497(10) 0.741(2) -0.3501(6) 0.027(3) Uani 1 1 d . . . O2 O 0.9593(10) 0.4332(18) -0.2730(6) 0.024(3) Uani 1 1 d . . . C1 C 0.6753(13) 1.168(2) -0.2099(9) 0.0179(11) Uani 1 1 d . . . C2 C 0.7337(13) 1.072(2) -0.2705(9) 0.0179(11) Uani 1 1 d . . . H2 H 0.7365 1.1188 -0.3201 0.022 Uiso 1 1 calc R . . C3 C 0.7853(13) 0.893(2) -0.2380(9) 0.0179(11) Uani 1 1 d . . . C4 C 0.7734(13) 0.857(2) -0.1611(9) 0.0179(11) Uani 1 1 d . . . C5 C 0.8469(13) 0.739(2) -0.2829(9) 0.0179(11) Uani 1 1 d . . . C6 C 0.9022(13) 0.554(2) -0.2365(9) 0.0179(11) Uani 1 1 d . . . C7 C 0.8799(13) 0.529(2) -0.1578(9) 0.0179(11) Uani 1 1 d . . . C8 C 0.8183(13) 0.679(2) -0.1206(9) 0.0179(11) Uani 1 1 d . . . C9 C 0.9111(13) 0.370(2) -0.1073(9) 0.0179(11) Uani 1 1 d . . . H9 H 0.9533 0.2580 -0.1217 0.022 Uiso 1 1 calc R . . C10 C 0.8761(13) 0.387(2) -0.0352(9) 0.0179(11) 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 I1 0.0362(7) 0.0172(6) 0.0447(8) -0.0014(5) -0.0038(5) 0.0044(5) I2 0.0384(7) 0.0133(5) 0.0134(5) 0.0032(4) 0.0049(4) 0.0020(5) S1 0.033(2) 0.0147(19) 0.020(2) 0.0000(16) 0.0031(17) 0.0026(17) S2 0.039(2) 0.0117(18) 0.0108(17) 0.0000(14) 0.0055(16) 0.0034(16) O1 0.039(7) 0.026(7) 0.017(6) -0.001(5) 0.001(5) -0.003(6) O2 0.045(7) 0.014(6) 0.014(6) -0.006(5) 0.002(5) 0.006(5) C1 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2) C2 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2) C3 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2) C4 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2) C5 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2) C6 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2) C7 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2) C8 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2) C9 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(2) C10 0.028(3) 0.010(2) 0.016(2) 0.002(2) 0.002(2) -0.002(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 I1 C1 2.105(16) . ? I2 C10 2.054(16) . ? S1 C1 1.693(16) . ? S1 C4 1.748(17) . ? S2 C8 1.697(16) . ? S2 C10 1.750(16) . ? O1 C5 1.196(19) . ? O2 C6 1.25(2) . ? C1 C2 1.46(2) . ? C2 C3 1.42(2) . ? C2 H2 0.9300 . ? C3 C4 1.40(2) . ? C3 C5 1.50(2) . ? C4 C8 1.44(2) . ? C5 C6 1.58(2) . ? C6 C7 1.44(2) . ? C7 C9 1.40(2) . ? C7 C8 1.41(2) . ? C9 C10 1.38(2) . ? C9 H9 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 91.9(8) . . ? C8 S2 C10 92.2(8) . . ? C2 C1 S1 115.3(12) . . ? C2 C1 I1 123.2(11) . . ? S1 C1 I1 121.5(9) . . ? C3 C2 C1 105.7(13) . . ? C3 C2 H2 127.1 . . ? C1 C2 H2 127.1 . . ? C4 C3 C2 117.6(15) . . ? C4 C3 C5 119.3(14) . . ? C2 C3 C5 123.0(14) . . ? C3 C4 C8 124.0(15) . . ? C3 C4 S1 109.4(12) . . ? C8 C4 S1 126.4(12) . . ? O1 C5 C3 123.9(15) . . ? O1 C5 C6 120.0(14) . . ? C3 C5 C6 115.8(13) . . ? O2 C6 C7 125.0(15) . . ? O2 C6 C5 116.0(13) . . ? C7 C6 C5 119.0(14) . . ? C9 C7 C8 109.5(14) . . ? C9 C7 C6 129.6(15) . . ? C8 C7 C6 120.9(14) . . ? C7 C8 C4 120.6(14) . . ? C7 C8 S2 113.0(12) . . ? C4 C8 S2 126.3(12) . . ? C10 C9 C7 116.4(15) . . ? C10 C9 H9 121.8 . . ? C7 C9 H9 121.8 . . ? C9 C10 S2 108.8(12) . . ? C9 C10 I2 130.6(12) . . ? S2 C10 I2 120.4(8) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 4.221 _refine_diff_density_min -2.522 _refine_diff_density_rms 0.376 data_str81 _database_code_depnum_ccdc_archive 'CCDC 914108' #TrackingRef '5a.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Dibromo-benzo[1,2-b:6,5-b']dithiophene-4,5-bis(ethyleneoxolane) ; _chemical_name_common ; 2,7-Dibromo-benzo[1,2-b:6,5-b']dithiophene-4,5-bis(ethyleneoxolane) ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Br2 O4 S2' _chemical_formula_sum 'C14 H10 Br2 O4 S2' _chemical_formula_weight 466.16 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4/ncc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x, z' '-x+1/2, -y+1/2, z' 'y, -x+1/2, z' 'x+1/2, -y, -z+1/2' 'y+1/2, x+1/2, -z+1/2' '-x, y+1/2, -z+1/2' '-y, -x, -z+1/2' '-x, -y, -z' 'y-1/2, -x, -z' 'x-1/2, y-1/2, -z' '-y, x-1/2, -z' '-x-1/2, y, z-1/2' '-y-1/2, -x-1/2, z-1/2' 'x, -y-1/2, z-1/2' 'y, x, z-1/2' _cell_length_a 20.229(5) _cell_length_b 20.229(5) _cell_length_c 7.688(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3146.0(16) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.968 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1824 _exptl_absorpt_coefficient_mu 5.432 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.214 _exptl_absorpt_correction_T_max 0.440 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36000 _diffrn_reflns_av_R_equivalents 0.2325 _diffrn_reflns_av_sigmaI/netI 0.0670 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1554 _reflns_number_gt 995 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0580P)^2^+3.5417P] 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 1554 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1073 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 Br1 Br 0.14071(3) 0.31110(3) 0.39061(11) 0.0626(3) Uani 1 1 d . . . S1 S 0.02847(7) 0.40720(7) 0.2913(2) 0.0443(4) Uani 1 1 d . . . O1 O 0.11455(18) 0.60078(17) 0.4869(5) 0.0386(9) Uani 1 1 d . . . O2 O 0.19179(16) 0.58903(18) 0.2773(5) 0.0379(9) Uani 1 1 d . . . C1 C 0.1097(3) 0.3970(3) 0.3467(8) 0.0440(15) Uani 1 1 d . . . C2 C 0.1444(3) 0.4547(3) 0.3515(7) 0.0388(13) Uani 1 1 d . . . H2 H 0.1891 0.4578 0.3795 0.047 Uiso 1 1 calc R . . C3 C 0.1040(3) 0.5091(3) 0.3084(7) 0.0354(12) Uani 1 1 d . . . C4 C 0.0402(3) 0.4911(2) 0.2727(7) 0.0362(13) Uani 1 1 d . . . C5 C 0.1237(2) 0.5810(3) 0.3131(7) 0.0357(13) Uani 1 1 d . . . C6 C 0.2078(3) 0.5755(3) 0.1003(8) 0.0443(15) Uani 1 1 d . . . H6A H 0.1960 0.5302 0.0723 0.053 Uiso 1 1 calc R . . H6B H 0.2550 0.5807 0.0823 0.053 Uiso 1 1 calc R . . C7 C 0.1219(3) 0.6708(3) 0.5159(8) 0.0462(15) Uani 1 1 d . . . H7A H 0.1671 0.6840 0.4914 0.055 Uiso 1 1 calc R . . H7B H 0.1124 0.6811 0.6365 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0510(4) 0.0317(4) 0.1050(7) 0.0103(3) -0.0004(4) 0.0044(3) S1 0.0381(8) 0.0319(7) 0.0630(11) 0.0018(7) 0.0007(7) -0.0039(6) O1 0.045(2) 0.033(2) 0.037(2) 0.0010(17) -0.0022(19) -0.0007(16) O2 0.0304(18) 0.043(2) 0.040(2) -0.0012(19) -0.0001(17) -0.0012(16) C1 0.043(3) 0.029(3) 0.060(4) 0.007(3) 0.006(3) 0.004(2) C2 0.035(3) 0.032(3) 0.049(4) 0.004(2) -0.002(3) 0.005(2) C3 0.038(3) 0.033(3) 0.035(3) 0.001(2) 0.000(3) 0.002(2) C4 0.037(3) 0.030(3) 0.042(3) 0.000(3) 0.005(3) 0.000(2) C5 0.028(3) 0.041(3) 0.038(3) 0.002(3) -0.003(2) -0.005(2) C6 0.035(3) 0.047(3) 0.051(4) 0.002(3) 0.004(3) -0.002(3) C7 0.059(4) 0.036(3) 0.044(4) -0.008(3) -0.006(3) -0.002(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 Br1 C1 1.877(5) . ? S1 C1 1.710(6) . ? S1 C4 1.719(5) . ? O1 C5 1.407(7) . ? O1 C7 1.442(6) . ? O2 C5 1.414(6) . ? O2 C6 1.426(7) . ? C1 C2 1.363(8) . ? C2 C3 1.411(7) . ? C3 C4 1.368(7) . ? C3 C5 1.510(7) . ? C4 C4 1.448(10) 6_455 ? C5 C5 1.558(11) 6_455 ? C6 C7 1.497(8) 6_455 ? C7 C6 1.497(8) 6_455 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C4 90.4(3) . . ? C5 O1 C7 114.3(4) . . ? C5 O2 C6 112.6(4) . . ? C2 C1 S1 113.5(4) . . ? C2 C1 Br1 128.0(4) . . ? S1 C1 Br1 118.6(3) . . ? C1 C2 C3 111.2(5) . . ? C4 C3 C2 112.8(5) . . ? C4 C3 C5 120.7(4) . . ? C2 C3 C5 126.4(5) . . ? C3 C4 C4 120.9(3) . 6_455 ? C3 C4 S1 112.1(4) . . ? C4 C4 S1 127.06(19) 6_455 . ? O1 C5 O2 106.3(4) . . ? O1 C5 C3 105.2(4) . . ? O2 C5 C3 111.3(4) . . ? O1 C5 C5 111.2(6) . 6_455 ? O2 C5 C5 110.8(4) . 6_455 ? C3 C5 C5 111.9(3) . 6_455 ? O2 C6 C7 109.6(5) . 6_455 ? O1 C7 C6 109.5(5) . 6_455 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.840 _refine_diff_density_min -0.537 _refine_diff_density_rms 0.106 data_str6 _database_code_depnum_ccdc_archive 'CCDC 914109' #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Difluoro-benzo[1,2-b:6,5-b']dithiophene-4,5-bis-(ethyleneoxolane) ; _chemical_name_common ; 2,7-Difluoro-benzo[1,2-b:6,5-b']dithiophene-4,5-bis-(ethyleneoxolane) ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 F2 O4 S2' _chemical_formula_sum 'C14 H10 F2 O4 S2' _chemical_formula_weight 344.34 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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.907(3) _cell_length_b 10.238(3) _cell_length_c 10.674(4) _cell_angle_alpha 100.888(6) _cell_angle_beta 103.524(6) _cell_angle_gamma 99.264(4) _cell_volume 703.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4232 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 30.14 _exptl_crystal_description plates _exptl_crystal_colour black _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.416 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9161 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0186 _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 -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2769 _reflns_number_gt 2436 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0342P)^2^+0.2311P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2769 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0746 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.29621(6) 0.07450(4) -0.07321(4) 0.04132(12) Uani 1 1 d . . . S2 S 0.27621(7) -0.05432(4) 0.20983(5) 0.04476(13) Uani 1 1 d . . . F1 F 0.26250(19) 0.20359(13) -0.26671(10) 0.0634(3) Uani 1 1 d . . . F2 F 0.2662(2) -0.09854(13) 0.44418(13) 0.0788(4) Uani 1 1 d . . . O1 O -0.12233(15) 0.29274(12) 0.12109(11) 0.0430(3) Uani 1 1 d . . . O2 O 0.08932(18) 0.37740(12) 0.39123(11) 0.0465(3) Uani 1 1 d . . . O3 O 0.39502(16) 0.40623(11) 0.34376(10) 0.0390(3) Uani 1 1 d . . . O4 O 0.11441(17) 0.48603(11) 0.15658(11) 0.0410(3) Uani 1 1 d . . . C1 C 0.2413(3) 0.20687(18) -0.14345(15) 0.0428(4) Uani 1 1 d . . . C5 C 0.0894(2) 0.34636(15) 0.15757(15) 0.0320(3) Uani 1 1 d . . . C8 C 0.2390(2) 0.10297(15) 0.18531(14) 0.0323(3) Uani 1 1 d . . . C7 C 0.2119(2) 0.18332(15) 0.29487(14) 0.0341(3) Uani 1 1 d . . . C4 C 0.2300(2) 0.15038(15) 0.06545(14) 0.0312(3) Uani 1 1 d . . . C3 C 0.1685(2) 0.26840(15) 0.05230(14) 0.0309(3) Uani 1 1 d . . . C6 C 0.1933(2) 0.32885(15) 0.29805(14) 0.0340(3) Uani 1 1 d . . . C2 C 0.1748(2) 0.30234(16) -0.07000(15) 0.0371(3) Uani 1 1 d . . . H13A H 0.1384 0.3790 -0.0953 0.045 Uiso 1 1 calc R . . C11 C 0.3233(3) 0.55871(16) 0.20300(18) 0.0454(4) Uani 1 1 d . . . H14A H 0.3309 0.6537 0.2010 0.055 Uiso 1 1 calc R . . H14B H 0.4003 0.5209 0.1453 0.055 Uiso 1 1 calc R . . C12 C 0.4130(3) 0.54800(16) 0.34115(17) 0.0466(4) Uani 1 1 d . . . H15A H 0.5554 0.5944 0.3714 0.056 Uiso 1 1 calc R . . H15B H 0.3418 0.5910 0.4001 0.056 Uiso 1 1 calc R . . C9 C 0.2185(3) 0.11904(18) 0.40245(16) 0.0467(4) Uani 1 1 d . . . H16A H 0.2020 0.1583 0.4842 0.056 Uiso 1 1 calc R . . C13 C -0.2205(3) 0.3467(2) 0.2187(2) 0.0549(5) Uani 1 1 d . . . H17A H -0.3649 0.3050 0.1899 0.066 Uiso 1 1 calc R . . H17B H -0.2060 0.4442 0.2281 0.066 Uiso 1 1 calc R . . C14 C -0.1265(3) 0.3186(2) 0.3489(2) 0.0567(5) Uani 1 1 d . . . H18A H -0.1907 0.3568 0.4146 0.068 Uiso 1 1 calc R . . H18B H -0.1483 0.2210 0.3407 0.068 Uiso 1 1 calc R . . C10 C 0.2520(3) -0.00682(19) 0.36833(18) 0.0514(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0461(2) 0.0457(2) 0.0377(2) 0.00697(17) 0.02029(18) 0.01621(18) S2 0.0499(2) 0.0377(2) 0.0550(3) 0.01937(19) 0.0184(2) 0.01677(18) F1 0.0808(8) 0.0830(8) 0.0363(5) 0.0195(5) 0.0303(5) 0.0179(6) F2 0.1092(10) 0.0724(8) 0.0726(8) 0.0506(7) 0.0262(7) 0.0284(7) O1 0.0278(5) 0.0526(7) 0.0487(7) 0.0079(5) 0.0121(5) 0.0114(5) O2 0.0536(7) 0.0493(7) 0.0406(6) 0.0030(5) 0.0259(5) 0.0122(5) O3 0.0369(6) 0.0382(6) 0.0368(6) 0.0060(5) 0.0056(5) 0.0042(5) O4 0.0418(6) 0.0348(6) 0.0511(7) 0.0134(5) 0.0141(5) 0.0155(5) C1 0.0439(9) 0.0569(10) 0.0310(8) 0.0144(7) 0.0153(7) 0.0084(8) C5 0.0287(7) 0.0331(7) 0.0366(8) 0.0091(6) 0.0108(6) 0.0101(6) C8 0.0309(7) 0.0332(7) 0.0353(8) 0.0113(6) 0.0102(6) 0.0090(6) C7 0.0338(7) 0.0375(8) 0.0319(8) 0.0111(6) 0.0089(6) 0.0066(6) C4 0.0289(7) 0.0353(8) 0.0308(7) 0.0073(6) 0.0106(6) 0.0081(6) C3 0.0268(7) 0.0359(8) 0.0301(7) 0.0088(6) 0.0072(6) 0.0065(6) C6 0.0361(8) 0.0362(8) 0.0313(7) 0.0056(6) 0.0142(6) 0.0076(6) C2 0.0366(8) 0.0423(9) 0.0348(8) 0.0152(7) 0.0091(6) 0.0088(7) C11 0.0494(9) 0.0326(8) 0.0560(10) 0.0117(7) 0.0180(8) 0.0069(7) C12 0.0501(10) 0.0344(8) 0.0489(10) 0.0011(7) 0.0134(8) 0.0015(7) C9 0.0575(10) 0.0515(10) 0.0333(8) 0.0159(7) 0.0132(8) 0.0095(8) C13 0.0379(9) 0.0646(12) 0.0720(13) 0.0142(10) 0.0299(9) 0.0190(8) C14 0.0539(11) 0.0618(12) 0.0663(12) 0.0115(9) 0.0412(10) 0.0140(9) C10 0.0592(11) 0.0530(11) 0.0491(10) 0.0307(8) 0.0129(8) 0.0130(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.7202(18) . ? S1 C4 1.7320(15) . ? S2 C10 1.725(2) . ? S2 C8 1.7288(15) . ? F1 C1 1.3524(19) . ? F2 C10 1.352(2) . ? O1 C5 1.4094(18) . ? O1 C13 1.444(2) . ? O2 C6 1.4190(18) . ? O2 C14 1.443(2) . ? O3 C6 1.4101(18) . ? O3 C12 1.443(2) . ? O4 C5 1.4148(18) . ? O4 C11 1.436(2) . ? C1 C2 1.343(2) . ? C5 C3 1.512(2) . ? C5 C6 1.560(2) . ? C8 C7 1.367(2) . ? C8 C4 1.443(2) . ? C7 C9 1.423(2) . ? C7 C6 1.511(2) . ? C4 C3 1.364(2) . ? C3 C2 1.421(2) . ? C2 H13A 0.9300 . ? C11 C12 1.492(2) . ? C11 H14A 0.9700 . ? C11 H14B 0.9700 . ? C12 H15A 0.9700 . ? C12 H15B 0.9700 . ? C9 C10 1.343(3) . ? C9 H16A 0.9300 . ? C13 C14 1.492(3) . ? C13 H17A 0.9700 . ? C13 H17B 0.9700 . ? C14 H18A 0.9700 . ? C14 H18B 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 C1 S1 C4 89.11(8) . . ? C10 S2 C8 89.09(8) . . ? C5 O1 C13 113.04(13) . . ? C6 O2 C14 112.91(12) . . ? C6 O3 C12 114.18(12) . . ? C5 O4 C11 113.38(11) . . ? C2 C1 F1 126.38(16) . . ? C2 C1 S1 115.59(12) . . ? F1 C1 S1 118.00(13) . . ? O1 C5 O4 106.47(11) . . ? O1 C5 C3 105.60(12) . . ? O4 C5 C3 111.67(12) . . ? O1 C5 C6 111.13(12) . . ? O4 C5 C6 110.48(12) . . ? C3 C5 C6 111.30(12) . . ? C7 C8 C4 120.79(14) . . ? C7 C8 S2 112.20(11) . . ? C4 C8 S2 126.99(11) . . ? C8 C7 C9 113.39(14) . . ? C8 C7 C6 120.69(13) . . ? C9 C7 C6 125.77(14) . . ? C3 C4 C8 120.99(13) . . ? C3 C4 S1 111.91(11) . . ? C8 C4 S1 127.09(11) . . ? C4 C3 C2 113.69(13) . . ? C4 C3 C5 120.84(13) . . ? C2 C3 C5 125.35(13) . . ? O3 C6 O2 106.80(12) . . ? O3 C6 C7 105.27(12) . . ? O2 C6 C7 111.97(12) . . ? O3 C6 C5 110.19(12) . . ? O2 C6 C5 110.82(12) . . ? C7 C6 C5 111.54(12) . . ? C1 C2 C3 109.69(14) . . ? C1 C2 H13A 125.2 . . ? C3 C2 H13A 125.2 . . ? O4 C11 C12 109.85(14) . . ? O4 C11 H14A 109.7 . . ? C12 C11 H14A 109.7 . . ? O4 C11 H14B 109.7 . . ? C12 C11 H14B 109.7 . . ? H14A C11 H14B 108.2 . . ? O3 C12 C11 109.24(13) . . ? O3 C12 H15A 109.8 . . ? C11 C12 H15A 109.8 . . ? O3 C12 H15B 109.8 . . ? C11 C12 H15B 109.8 . . ? H15A C12 H15B 108.3 . . ? C10 C9 C7 109.89(16) . . ? C10 C9 H16A 125.1 . . ? C7 C9 H16A 125.1 . . ? O1 C13 C14 109.87(14) . . ? O1 C13 H17A 109.7 . . ? C14 C13 H17A 109.7 . . ? O1 C13 H17B 109.7 . . ? C14 C13 H17B 109.7 . . ? H17A C13 H17B 108.2 . . ? O2 C14 C13 110.18(15) . . ? O2 C14 H18A 109.6 . . ? C13 C14 H18A 109.6 . . ? O2 C14 H18B 109.6 . . ? C13 C14 H18B 109.6 . . ? H18A C14 H18B 108.1 . . ? C9 C10 F2 126.90(18) . . ? C9 C10 S2 115.43(13) . . ? F2 C10 S2 117.67(15) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.296 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.037 data_str7 _database_code_depnum_ccdc_archive 'CCDC 914110' #TrackingRef '7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Dibromo-benzo[1,2-b:6,5-b']dithiophene-4,5-bis-(1,3-dioxolane) ; _chemical_name_common ; 2,7-Dibromo-benzo[1,2-b:6,5-b']dithiophene-4,5-bis-(1,3-dioxolane) ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Br2 O4 S2' _chemical_formula_sum 'C14 H10 Br2 O4 S2' _chemical_formula_weight 466.16 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall -P2yn 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 14.021(4) _cell_length_b 7.945(2) _cell_length_c 14.062(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.009(7) _cell_angle_gamma 90.00 _cell_volume 1560.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.984 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 5.476 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.120 _exptl_absorpt_correction_T_max 0.383 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8859 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2751 _reflns_number_gt 2430 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0294P)^2^+0.6086P] 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 2751 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0260 _refine_ls_R_factor_gt 0.0211 _refine_ls_wR_factor_ref 0.0545 _refine_ls_wR_factor_gt 0.0524 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.645607(16) 0.61895(3) 0.179494(19) 0.04223(9) Uani 1 1 d . . . Br2 Br 1.18863(2) 0.06009(4) -0.06545(2) 0.05405(10) Uani 1 1 d . . . S1 S 0.80557(4) 0.41925(8) 0.09137(4) 0.03609(14) Uani 1 1 d . . . S2 S 1.00795(4) 0.24115(7) -0.00575(4) 0.03666(14) Uani 1 1 d . . . O1 O 1.08418(11) 0.6573(2) 0.23310(12) 0.0380(4) Uani 1 1 d . . . O2 O 1.02719(12) 0.5683(2) 0.37152(11) 0.0421(4) Uani 1 1 d . . . O3 O 1.19002(10) 0.3940(2) 0.29943(11) 0.0362(4) Uani 1 1 d . . . O4 O 1.05891(10) 0.23419(19) 0.32555(11) 0.0343(4) Uani 1 1 d . . . C1 C 0.77326(16) 0.5459(3) 0.18225(17) 0.0340(5) Uani 1 1 d . . . C2 C 0.84753(16) 0.5821(3) 0.24758(17) 0.0320(5) Uani 1 1 d . . . H2 H 0.8424 0.6487 0.3013 0.038 Uiso 1 1 calc R . . C3 C 0.93380(15) 0.5060(3) 0.22387(15) 0.0278(5) Uani 1 1 d . . . C4 C 0.92235(15) 0.4144(3) 0.14122(15) 0.0291(5) Uani 1 1 d . . . C5 C 1.03382(15) 0.5251(3) 0.27472(15) 0.0298(5) Uani 1 1 d . . . C6 C 1.09365(15) 0.3621(3) 0.26568(15) 0.0287(5) Uani 1 1 d . . . C7 C 1.08513(15) 0.2994(3) 0.16379(15) 0.0289(5) Uani 1 1 d . . . C8 C 1.00169(15) 0.3238(3) 0.10650(15) 0.0296(5) Uani 1 1 d . . . C9 C 1.15490(16) 0.2091(3) 0.11745(17) 0.0341(5) Uani 1 1 d . . . H9 H 1.2150 0.1796 0.1459 0.041 Uiso 1 1 calc R . . C10 C 1.12267(17) 0.1713(3) 0.02632(17) 0.0363(5) Uani 1 1 d . . . C11 C 1.0705(2) 0.8041(3) 0.2880(2) 0.0606(8) Uani 1 1 d . . . H11B H 1.0119 0.8619 0.2655 0.073 Uiso 1 1 calc R . . H11A H 1.1240 0.8811 0.2862 0.073 Uiso 1 1 calc R . . C12 C 1.0645(2) 0.7345(4) 0.3860(2) 0.0645(9) Uani 1 1 d . . . H12B H 1.1274 0.7314 0.4209 0.077 Uiso 1 1 calc R . . H12A H 1.0223 0.8023 0.4214 0.077 Uiso 1 1 calc R . . C13 C 1.12714(17) 0.2219(3) 0.40791(17) 0.0413(6) Uani 1 1 d . . . H13B H 1.1287 0.1092 0.4345 0.050 Uiso 1 1 calc R . . H13A H 1.1129 0.3017 0.4569 0.050 Uiso 1 1 calc R . . C14 C 1.21922(17) 0.2642(3) 0.36714(18) 0.0433(6) Uani 1 1 d . . . H14B H 1.2665 0.3055 0.4160 0.052 Uiso 1 1 calc R . . H14A H 1.2450 0.1676 0.3360 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02616(13) 0.04396(16) 0.05655(17) 0.00013(12) 0.00353(10) 0.00669(10) Br2 0.0718(2) 0.04476(17) 0.05000(17) -0.00238(12) 0.03023(14) 0.01126(14) S1 0.0287(3) 0.0377(3) 0.0402(3) -0.0063(3) -0.0064(2) 0.0042(2) S2 0.0437(3) 0.0353(3) 0.0309(3) -0.0043(3) 0.0022(2) 0.0025(3) O1 0.0385(9) 0.0275(8) 0.0480(10) -0.0029(7) 0.0036(7) -0.0074(7) O2 0.0437(10) 0.0478(10) 0.0342(9) -0.0127(8) 0.0001(7) 0.0005(8) O3 0.0221(8) 0.0406(9) 0.0447(9) 0.0035(8) -0.0042(7) -0.0056(7) O4 0.0300(8) 0.0347(9) 0.0376(9) 0.0062(7) -0.0011(6) -0.0070(7) C1 0.0284(12) 0.0296(12) 0.0438(13) -0.0007(10) 0.0026(10) 0.0047(9) C2 0.0318(12) 0.0283(12) 0.0359(12) -0.0041(10) 0.0038(9) 0.0007(10) C3 0.0272(11) 0.0236(11) 0.0321(11) 0.0018(9) 0.0006(9) 0.0005(9) C4 0.0249(11) 0.0288(12) 0.0331(11) 0.0023(9) -0.0009(9) 0.0001(9) C5 0.0273(11) 0.0305(12) 0.0313(12) -0.0028(9) 0.0013(9) -0.0027(9) C6 0.0207(10) 0.0302(12) 0.0351(12) 0.0014(9) 0.0011(9) -0.0038(9) C7 0.0276(11) 0.0238(11) 0.0356(12) 0.0004(9) 0.0044(9) -0.0010(9) C8 0.0313(11) 0.0247(11) 0.0330(12) -0.0027(9) 0.0032(9) 0.0016(9) C9 0.0292(11) 0.0302(12) 0.0434(13) 0.0012(10) 0.0057(10) 0.0018(9) C10 0.0428(14) 0.0278(12) 0.0404(13) -0.0004(10) 0.0157(10) 0.0033(10) C11 0.0514(17) 0.0313(15) 0.101(3) -0.0201(16) 0.0164(16) -0.0021(12) C12 0.0519(17) 0.064(2) 0.080(2) -0.0455(18) 0.0151(15) -0.0123(15) C13 0.0444(14) 0.0443(15) 0.0333(13) 0.0085(11) -0.0080(10) -0.0011(12) C14 0.0337(13) 0.0481(15) 0.0458(14) 0.0063(12) -0.0101(11) 0.0023(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.879(2) . ? Br2 C10 1.874(2) . ? S1 C1 1.718(2) . ? S1 C4 1.724(2) . ? S2 C8 1.719(2) . ? S2 C10 1.724(2) . ? O1 C5 1.420(3) . ? O1 C11 1.420(3) . ? O2 C5 1.415(3) . ? O2 C12 1.428(3) . ? O3 C6 1.415(2) . ? O3 C14 1.438(3) . ? O4 C6 1.432(3) . ? O4 C13 1.440(3) . ? C1 C2 1.358(3) . ? C2 C3 1.418(3) . ? C2 H2 0.9300 . ? C3 C4 1.369(3) . ? C3 C5 1.525(3) . ? C4 C8 1.445(3) . ? C5 C6 1.554(3) . ? C6 C7 1.512(3) . ? C7 C8 1.375(3) . ? C7 C9 1.417(3) . ? C9 C10 1.355(3) . ? C9 H9 0.9300 . ? C11 C12 1.494(5) . ? C11 H11B 0.9700 . ? C11 H11A 0.9700 . ? C12 H12B 0.9700 . ? C12 H12A 0.9700 . ? C13 C14 1.496(4) . ? C13 H13B 0.9700 . ? C13 H13A 0.9700 . ? C14 H14B 0.9700 . ? C14 H14A 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 C1 S1 C4 90.77(11) . . ? C8 S2 C10 90.23(11) . . ? C5 O1 C11 106.72(19) . . ? C5 O2 C12 107.9(2) . . ? C6 O3 C14 107.59(16) . . ? C6 O4 C13 106.55(16) . . ? C2 C1 S1 113.01(17) . . ? C2 C1 Br1 128.41(18) . . ? S1 C1 Br1 118.57(13) . . ? C1 C2 C3 111.7(2) . . ? C1 C2 H2 124.1 . . ? C3 C2 H2 124.1 . . ? C4 C3 C2 112.77(19) . . ? C4 C3 C5 119.07(19) . . ? C2 C3 C5 128.02(19) . . ? C3 C4 C8 121.00(19) . . ? C3 C4 S1 111.72(16) . . ? C8 C4 S1 127.24(17) . . ? O2 C5 O1 107.08(17) . . ? O2 C5 C3 109.89(17) . . ? O1 C5 C3 110.50(17) . . ? O2 C5 C6 111.23(17) . . ? O1 C5 C6 106.94(17) . . ? C3 C5 C6 111.08(17) . . ? O3 C6 O4 107.07(16) . . ? O3 C6 C7 111.77(18) . . ? O4 C6 C7 108.67(17) . . ? O3 C6 C5 109.27(17) . . ? O4 C6 C5 109.25(17) . . ? C7 C6 C5 110.72(17) . . ? C8 C7 C9 112.8(2) . . ? C8 C7 C6 120.10(19) . . ? C9 C7 C6 127.0(2) . . ? C7 C8 C4 120.9(2) . . ? C7 C8 S2 112.03(16) . . ? C4 C8 S2 127.09(17) . . ? C10 C9 C7 111.1(2) . . ? C10 C9 H9 124.4 . . ? C7 C9 H9 124.4 . . ? C9 C10 S2 113.75(17) . . ? C9 C10 Br2 127.74(19) . . ? S2 C10 Br2 118.49(14) . . ? O1 C11 C12 102.6(2) . . ? O1 C11 H11B 111.2 . . ? C12 C11 H11B 111.2 . . ? O1 C11 H11A 111.2 . . ? C12 C11 H11A 111.2 . . ? H11B C11 H11A 109.2 . . ? O2 C12 C11 105.0(2) . . ? O2 C12 H12B 110.7 . . ? C11 C12 H12B 110.7 . . ? O2 C12 H12A 110.7 . . ? C11 C12 H12A 110.7 . . ? H12B C12 H12A 108.8 . . ? O4 C13 C14 102.22(18) . . ? O4 C13 H13B 111.3 . . ? C14 C13 H13B 111.3 . . ? O4 C13 H13A 111.3 . . ? C14 C13 H13A 111.3 . . ? H13B C13 H13A 109.2 . . ? O3 C14 C13 102.08(18) . . ? O3 C14 H14B 111.4 . . ? C13 C14 H14B 111.4 . . ? O3 C14 H14A 111.4 . . ? C13 C14 H14A 111.4 . . ? H14B C14 H14A 109.2 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.241 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.062 data_paul103n _database_code_depnum_ccdc_archive 'CCDC 914111' #TrackingRef '8b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-Dibromo-4H-cyclopenta[1,2-b:5,4-b']dithiophen-4-one ; _chemical_name_common ; 2,6-Dibromo-4H-cyclopenta[1,2-b:5,4-b']dithiophen-4-one ; _chemical_melting_point ? _chemical_formula_moiety 'C9 H2 Br2 O S2' _chemical_formula_sum 'C9 H2 Br2 O S2' _chemical_formula_weight 350.05 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.2936(10) _cell_length_b 20.532(3) _cell_length_c 26.509(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3969.7(9) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9671 _cell_measurement_theta_min 3.0738 _cell_measurement_theta_max 29.1587 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2656 _exptl_absorpt_coefficient_mu 8.545 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4820 _exptl_absorpt_correction_T_max 0.6746 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 44216 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 24.99 _reflns_number_total 6978 _reflns_number_gt 6179 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0000P)^2^+78.6665P] 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 0.503(18) _refine_ls_number_reflns 6978 _refine_ls_number_parameters 296 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1090 _refine_ls_wR_factor_gt 0.1054 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 Br1A Br -0.11162(19) 0.27601(5) 0.36745(4) 0.0192(2) Uani 1 1 d . . . Br2A Br 0.5835(2) 0.69173(5) 0.40211(4) 0.0271(3) Uani 1 1 d . . . S1A S 0.1136(5) 0.39142(12) 0.41069(8) 0.0133(6) Uani 1 1 d . . . S2A S 0.3884(5) 0.56103(12) 0.42513(9) 0.0158(6) Uani 1 1 d . . . O1A O 0.2525(11) 0.4989(4) 0.2471(2) 0.0146(7) Uani 1 1 d . . . C1A C 0.0351(16) 0.3507(6) 0.3581(4) 0.0166(8) Uani 1 1 d . . . C2A C 0.0764(17) 0.3794(5) 0.3135(4) 0.0166(8) Uani 1 1 d . . . H2A H 0.0450 0.3628 0.2812 0.020 Uiso 1 1 calc R . . C3A C 0.1758(16) 0.4391(5) 0.3228(4) 0.0166(8) Uani 1 1 d . . . C4A C 0.2047(17) 0.4509(6) 0.3729(4) 0.0166(8) Uani 1 1 d . . . C5A C 0.2566(16) 0.4921(6) 0.2929(4) 0.0166(8) Uani 1 1 d . . . C6A C 0.3351(16) 0.5378(6) 0.3307(4) 0.0166(8) Uani 1 1 d . . . C7A C 0.3073(17) 0.5130(6) 0.3793(4) 0.0166(8) Uani 1 1 d . . . C8A C 0.4298(16) 0.5979(5) 0.3319(4) 0.0166(8) Uani 1 1 d . . . H8A H 0.4642 0.6222 0.3029 0.020 Uiso 1 1 calc R . . C9A C 0.4644(17) 0.6159(6) 0.3797(4) 0.0166(8) Uani 1 1 d . . . Br1B Br 1.08736(19) 0.68776(5) 0.48943(5) 0.0300(3) Uani 1 1 d . . . Br2B Br 0.38110(15) 0.27197(4) 0.49220(4) 0.0198(2) Uani 1 1 d . . . S1B S 0.8924(5) 0.56054(12) 0.45611(9) 0.0139(5) Uani 1 1 d . . . S2B S 0.6128(5) 0.39028(12) 0.45676(9) 0.0142(5) Uani 1 1 d . . . O1B O 0.7513(12) 0.4767(4) 0.6277(3) 0.0146(7) Uani 1 1 d . . . C1B C 0.9681(14) 0.6084(5) 0.5040(4) 0.0123(7) Uani 1 1 d . . . C2B C 0.9331(16) 0.5858(5) 0.5510(4) 0.0123(7) Uani 1 1 d . . . H2B H 0.9659 0.6071 0.5815 0.015 Uiso 1 1 calc R . . C3B C 0.8405(16) 0.5256(5) 0.5477(4) 0.0123(7) Uani 1 1 d . . . C4B C 0.8093(15) 0.5051(5) 0.4984(4) 0.0123(7) Uani 1 1 d . . . C5B C 0.7570(17) 0.4758(5) 0.5822(4) 0.0123(7) Uani 1 1 d . . . C6B C 0.6786(16) 0.4246(5) 0.5478(4) 0.0123(7) Uani 1 1 d . . . C7B C 0.7080(16) 0.4433(5) 0.4984(4) 0.0123(7) Uani 1 1 d . . . C8B C 0.5745(17) 0.3669(5) 0.5528(4) 0.0123(7) Uani 1 1 d . . . H8B H 0.5396 0.3475 0.5839 0.015 Uiso 1 1 calc R . . C9B C 0.5321(14) 0.3435(4) 0.5067(4) 0.0123(7) Uani 1 1 d . . . Br1C Br 1.1011(2) 0.70854(5) 0.26509(4) 0.0207(3) Uani 1 1 d . . . Br2C Br 0.41304(19) 0.29305(5) 0.21516(4) 0.0210(3) Uani 1 1 d . . . S1C S 0.8885(5) 0.59244(12) 0.21652(9) 0.0150(5) Uani 1 1 d . . . S2C S 0.6149(5) 0.42339(13) 0.19693(9) 0.0170(6) Uani 1 1 d . . . O1C O 0.7480(11) 0.4771(4) 0.3771(3) 0.0146(7) Uani 1 1 d . . . C1C C 0.9660(16) 0.6323(5) 0.2707(4) 0.0147(8) Uani 1 1 d . . . C2C C 0.9305(16) 0.5998(5) 0.3133(4) 0.0147(8) Uani 1 1 d . . . H2C H 0.9662 0.6137 0.3461 0.018 Uiso 1 1 calc R . . C3C C 0.8318(16) 0.5412(5) 0.3029(4) 0.0147(8) Uani 1 1 d . . . C4C C 0.8027(16) 0.5313(5) 0.2521(4) 0.0147(8) Uani 1 1 d . . . C5C C 0.7505(16) 0.4852(5) 0.3314(4) 0.0147(8) Uani 1 1 d . . . C6C C 0.6708(16) 0.4421(5) 0.2911(4) 0.0147(8) Uani 1 1 d . . . C7C C 0.7011(16) 0.4704(5) 0.2444(4) 0.0147(8) Uani 1 1 d . . . C8C C 0.5793(16) 0.3829(5) 0.2881(4) 0.0147(8) Uani 1 1 d . . . H8C H 0.5485 0.3567 0.3164 0.018 Uiso 1 1 calc R . . C9C C 0.5398(16) 0.3674(5) 0.2397(4) 0.0147(8) Uani 1 1 d . . . Br1D Br 0.60602(19) 0.72110(5) 0.15041(4) 0.0228(3) Uani 1 1 d . . . Br2D Br -0.0957(2) 0.30552(5) 0.11785(4) 0.0277(3) Uani 1 1 d . . . S1D S 0.3847(5) 0.59569(12) 0.17546(9) 0.0161(6) Uani 1 1 d . . . S2D S 0.1069(5) 0.42544(13) 0.16219(9) 0.0172(6) Uani 1 1 d . . . O1D O 0.2506(11) 0.5333(3) -0.0016(2) 0.0146(7) Uani 1 1 d . . . C1D C 0.4650(16) 0.6489(5) 0.1306(4) 0.0125(8) Uani 1 1 d . . . C2D C 0.4220(17) 0.6327(5) 0.0821(4) 0.0125(8) Uani 1 1 d . . . H2D H 0.4516 0.6572 0.0528 0.015 Uiso 1 1 calc R . . C3D C 0.3243(16) 0.5723(5) 0.0830(4) 0.0125(8) Uani 1 1 d . . . C4D C 0.2926(16) 0.5466(5) 0.1294(4) 0.0125(8) Uani 1 1 d . . . C5D C 0.2445(17) 0.5274(5) 0.0439(4) 0.0125(8) Uani 1 1 d . . . C6D C 0.1614(16) 0.4723(5) 0.0739(4) 0.0125(8) Uani 1 1 d . . . C7D C 0.1925(16) 0.4853(5) 0.1247(4) 0.0125(8) Uani 1 1 d . . . C8D C 0.0693(16) 0.4152(5) 0.0642(4) 0.0125(8) Uani 1 1 d . . . H8D H 0.0370 0.3997 0.0316 0.015 Uiso 1 1 calc R . . C9D C 0.0308(16) 0.3835(5) 0.1093(4) 0.0125(8) 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 Br1A 0.0206(6) 0.0172(5) 0.0197(5) -0.0052(4) -0.0032(5) -0.0002(5) Br2A 0.0342(8) 0.0163(5) 0.0307(6) 0.0072(4) -0.0071(6) -0.0085(6) S1A 0.0177(16) 0.0154(12) 0.0068(11) 0.0012(9) 0.0006(12) -0.0002(12) S2A 0.0204(16) 0.0169(12) 0.0101(11) 0.0004(9) 0.0008(12) -0.0029(13) O1A 0.0144(13) 0.0246(18) 0.0048(16) 0.0018(13) -0.0008(12) 0.0007(13) C1A 0.012(2) 0.0263(19) 0.0113(16) -0.0002(14) 0.0005(14) 0.0030(17) C2A 0.012(2) 0.0263(19) 0.0113(16) -0.0002(14) 0.0005(14) 0.0030(17) C3A 0.012(2) 0.0263(19) 0.0113(16) -0.0002(14) 0.0005(14) 0.0030(17) C4A 0.012(2) 0.0263(19) 0.0113(16) -0.0002(14) 0.0005(14) 0.0030(17) C5A 0.012(2) 0.0263(19) 0.0113(16) -0.0002(14) 0.0005(14) 0.0030(17) C6A 0.012(2) 0.0263(19) 0.0113(16) -0.0002(14) 0.0005(14) 0.0030(17) C7A 0.012(2) 0.0263(19) 0.0113(16) -0.0002(14) 0.0005(14) 0.0030(17) C8A 0.012(2) 0.0263(19) 0.0113(16) -0.0002(14) 0.0005(14) 0.0030(17) C9A 0.012(2) 0.0263(19) 0.0113(16) -0.0002(14) 0.0005(14) 0.0030(17) Br1B 0.0378(7) 0.0130(4) 0.0392(6) 0.0036(5) 0.0069(7) -0.0084(5) Br2B 0.0152(5) 0.0130(4) 0.0311(5) -0.0048(4) -0.0017(5) -0.0022(4) S1B 0.0189(16) 0.0147(11) 0.0080(10) 0.0032(9) 0.0024(12) -0.0029(12) S2B 0.0142(15) 0.0145(11) 0.0139(12) -0.0022(9) 0.0014(12) -0.0019(12) O1B 0.0144(13) 0.0246(18) 0.0048(16) 0.0018(13) -0.0008(12) 0.0007(13) C1B 0.012(2) 0.0114(15) 0.0131(16) 0.0008(13) 0.0004(14) -0.0006(14) C2B 0.012(2) 0.0114(15) 0.0131(16) 0.0008(13) 0.0004(14) -0.0006(14) C3B 0.012(2) 0.0114(15) 0.0131(16) 0.0008(13) 0.0004(14) -0.0006(14) C4B 0.012(2) 0.0114(15) 0.0131(16) 0.0008(13) 0.0004(14) -0.0006(14) C5B 0.012(2) 0.0114(15) 0.0131(16) 0.0008(13) 0.0004(14) -0.0006(14) C6B 0.012(2) 0.0114(15) 0.0131(16) 0.0008(13) 0.0004(14) -0.0006(14) C7B 0.012(2) 0.0114(15) 0.0131(16) 0.0008(13) 0.0004(14) -0.0006(14) C8B 0.012(2) 0.0114(15) 0.0131(16) 0.0008(13) 0.0004(14) -0.0006(14) C9B 0.012(2) 0.0114(15) 0.0131(16) 0.0008(13) 0.0004(14) -0.0006(14) Br1C 0.0269(7) 0.0235(5) 0.0117(5) -0.0016(4) -0.0008(5) -0.0078(6) Br2C 0.0271(7) 0.0225(5) 0.0135(5) -0.0013(4) -0.0035(5) -0.0034(5) S1C 0.0165(15) 0.0216(12) 0.0070(11) -0.0010(9) -0.0018(12) -0.0027(13) S2C 0.0175(15) 0.0232(13) 0.0103(11) 0.0033(10) -0.0022(12) -0.0029(13) O1C 0.0144(13) 0.0246(18) 0.0048(16) 0.0018(13) -0.0008(12) 0.0007(13) C1C 0.013(2) 0.0250(18) 0.0059(16) 0.0001(13) -0.0027(14) -0.0006(16) C2C 0.013(2) 0.0250(18) 0.0059(16) 0.0001(13) -0.0027(14) -0.0006(16) C3C 0.013(2) 0.0250(18) 0.0059(16) 0.0001(13) -0.0027(14) -0.0006(16) C4C 0.013(2) 0.0250(18) 0.0059(16) 0.0001(13) -0.0027(14) -0.0006(16) C5C 0.013(2) 0.0250(18) 0.0059(16) 0.0001(13) -0.0027(14) -0.0006(16) C6C 0.013(2) 0.0250(18) 0.0059(16) 0.0001(13) -0.0027(14) -0.0006(16) C7C 0.013(2) 0.0250(18) 0.0059(16) 0.0001(13) -0.0027(14) -0.0006(16) C8C 0.013(2) 0.0250(18) 0.0059(16) 0.0001(13) -0.0027(14) -0.0006(16) C9C 0.013(2) 0.0250(18) 0.0059(16) 0.0001(13) -0.0027(14) -0.0006(16) Br1D 0.0212(6) 0.0159(5) 0.0315(6) -0.0082(4) -0.0067(5) 0.0007(5) Br2D 0.0379(8) 0.0138(5) 0.0314(6) 0.0067(4) 0.0045(6) -0.0065(6) S1D 0.0155(15) 0.0201(12) 0.0128(12) -0.0045(9) -0.0009(12) 0.0008(13) S2D 0.0174(16) 0.0205(12) 0.0137(12) 0.0050(10) -0.0025(12) -0.0016(13) O1D 0.0144(13) 0.0246(18) 0.0048(16) 0.0018(13) -0.0008(12) 0.0007(13) C1D 0.012(2) 0.0109(16) 0.0151(17) 0.0017(13) 0.0000(14) -0.0009(15) C2D 0.012(2) 0.0109(16) 0.0151(17) 0.0017(13) 0.0000(14) -0.0009(15) C3D 0.012(2) 0.0109(16) 0.0151(17) 0.0017(13) 0.0000(14) -0.0009(15) C4D 0.012(2) 0.0109(16) 0.0151(17) 0.0017(13) 0.0000(14) -0.0009(15) C5D 0.012(2) 0.0109(16) 0.0151(17) 0.0017(13) 0.0000(14) -0.0009(15) C6D 0.012(2) 0.0109(16) 0.0151(17) 0.0017(13) 0.0000(14) -0.0009(15) C7D 0.012(2) 0.0109(16) 0.0151(17) 0.0017(13) 0.0000(14) -0.0009(15) C8D 0.012(2) 0.0109(16) 0.0151(17) 0.0017(13) 0.0000(14) -0.0009(15) C9D 0.012(2) 0.0109(16) 0.0151(17) 0.0017(13) 0.0000(14) -0.0009(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 Br1A C1A 1.886(12) . ? Br2A C9A 1.879(12) . ? S1A C4A 1.713(12) . ? S1A C1A 1.724(11) . ? S2A C7A 1.674(12) . ? S2A C9A 1.739(11) . ? O1A C5A 1.224(14) . ? C1A C2A 1.355(15) . ? C2A C3A 1.445(16) . ? C2A H2A 0.9500 . ? C3A C4A 1.367(15) . ? C3A C5A 1.469(16) . ? C4A C7A 1.488(17) . ? C5A C6A 1.488(15) . ? C6A C7A 1.399(15) . ? C6A C8A 1.414(16) . ? C8A C9A 1.345(15) . ? C8A H8A 0.9500 . ? Br1B C1B 1.886(10) . ? Br2B C9B 1.875(10) . ? S1B C1B 1.698(10) . ? S1B C4B 1.709(10) . ? S2B C7B 1.699(10) . ? S2B C9B 1.739(10) . ? O1B C5B 1.208(13) . ? C1B C2B 1.356(14) . ? C2B C3B 1.411(15) . ? C2B H2B 0.9500 . ? C3B C4B 1.392(15) . ? C3B C5B 1.500(15) . ? C4B C7B 1.467(14) . ? C5B C6B 1.506(15) . ? C6B C7B 1.381(15) . ? C6B C8B 1.414(15) . ? C8B C9B 1.349(14) . ? C8B H8B 0.9500 . ? Br1C C1C 1.855(12) . ? Br2C C9C 1.899(11) . ? S1C C4C 1.689(11) . ? S1C C1C 1.746(10) . ? S2C C9C 1.704(11) . ? S2C C7C 1.707(11) . ? O1C C5C 1.223(13) . ? C1C C2C 1.340(15) . ? C2C C3C 1.429(16) . ? C2C H2C 0.9500 . ? C3C C4C 1.380(14) . ? C3C C5C 1.496(15) . ? C4C C7C 1.468(15) . ? C5C C6C 1.503(14) . ? C6C C7C 1.385(15) . ? C6C C8C 1.389(16) . ? C8C C9C 1.355(14) . ? C8C H8C 0.9500 . ? Br1D C1D 1.879(11) . ? Br2D C9D 1.863(11) . ? S1D C1D 1.719(10) . ? S1D C4D 1.720(11) . ? S2D C7D 1.699(11) . ? S2D C9D 1.737(11) . ? O1D C5D 1.214(14) . ? C1D C2D 1.364(15) . ? C2D C3D 1.430(15) . ? C2D H2D 0.9500 . ? C3D C4D 1.357(15) . ? C3D C5D 1.505(15) . ? C4D C7D 1.462(15) . ? C5D C6D 1.509(15) . ? C6D C8D 1.376(15) . ? C6D C7D 1.390(15) . ? C8D C9D 1.389(14) . ? C8D H8D 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4A S1A C1A 90.1(5) . . ? C7A S2A C9A 89.5(6) . . ? C2A C1A S1A 114.9(9) . . ? C2A C1A Br1A 126.5(9) . . ? S1A C1A Br1A 118.5(6) . . ? C1A C2A C3A 109.4(9) . . ? C1A C2A H2A 125.3 . . ? C3A C2A H2A 125.3 . . ? C4A C3A C2A 113.1(10) . . ? C4A C3A C5A 109.3(10) . . ? C2A C3A C5A 137.5(10) . . ? C3A C4A C7A 109.8(10) . . ? C3A C4A S1A 112.5(9) . . ? C7A C4A S1A 137.7(8) . . ? O1A C5A C3A 127.6(10) . . ? O1A C5A C6A 127.3(10) . . ? C3A C5A C6A 105.0(9) . . ? C7A C6A C8A 111.6(10) . . ? C7A C6A C5A 109.5(10) . . ? C8A C6A C5A 138.9(10) . . ? C6A C7A C4A 106.3(9) . . ? C6A C7A S2A 113.7(9) . . ? C4A C7A S2A 139.9(9) . . ? C9A C8A C6A 110.6(10) . . ? C9A C8A H8A 124.7 . . ? C6A C8A H8A 124.7 . . ? C8A C9A S2A 114.5(9) . . ? C8A C9A Br2A 127.7(9) . . ? S2A C9A Br2A 117.8(6) . . ? C1B S1B C4B 90.6(5) . . ? C7B S2B C9B 89.9(5) . . ? C2B C1B S1B 115.3(8) . . ? C2B C1B Br1B 124.9(8) . . ? S1B C1B Br1B 119.8(6) . . ? C1B C2B C3B 109.5(9) . . ? C1B C2B H2B 125.3 . . ? C3B C2B H2B 125.3 . . ? C4B C3B C2B 113.7(9) . . ? C4B C3B C5B 107.5(9) . . ? C2B C3B C5B 138.8(10) . . ? C3B C4B C7B 110.1(8) . . ? C3B C4B S1B 110.9(7) . . ? C7B C4B S1B 139.0(8) . . ? O1B C5B C3B 127.8(10) . . ? O1B C5B C6B 127.1(10) . . ? C3B C5B C6B 105.1(9) . . ? C7B C6B C8B 114.0(9) . . ? C7B C6B C5B 108.7(9) . . ? C8B C6B C5B 137.1(10) . . ? C6B C7B C4B 108.6(9) . . ? C6B C7B S2B 111.9(8) . . ? C4B C7B S2B 139.5(8) . . ? C9B C8B C6B 109.7(9) . . ? C9B C8B H8B 125.2 . . ? C6B C8B H8B 125.2 . . ? C8B C9B S2B 114.5(8) . . ? C8B C9B Br2B 126.8(8) . . ? S2B C9B Br2B 118.4(6) . . ? C4C S1C C1C 90.6(5) . . ? C9C S2C C7C 90.5(5) . . ? C2C C1C S1C 113.4(9) . . ? C2C C1C Br1C 126.2(8) . . ? S1C C1C Br1C 120.2(6) . . ? C1C C2C C3C 110.8(9) . . ? C1C C2C H2C 124.6 . . ? C3C C2C H2C 124.6 . . ? C4C C3C C2C 112.9(10) . . ? C4C C3C C5C 108.6(9) . . ? C2C C3C C5C 138.5(9) . . ? C3C C4C C7C 109.7(10) . . ? C3C C4C S1C 112.3(9) . . ? C7C C4C S1C 138.0(8) . . ? O1C C5C C3C 127.6(10) . . ? O1C C5C C6C 128.0(10) . . ? C3C C5C C6C 104.4(9) . . ? C7C C6C C8C 113.1(9) . . ? C7C C6C C5C 109.0(10) . . ? C8C C6C C5C 137.9(10) . . ? C6C C7C C4C 108.3(9) . . ? C6C C7C S2C 111.3(8) . . ? C4C C7C S2C 140.3(8) . . ? C9C C8C C6C 111.2(9) . . ? C9C C8C H8C 124.4 . . ? C6C C8C H8C 124.4 . . ? C8C C9C S2C 113.8(9) . . ? C8C C9C Br2C 128.1(8) . . ? S2C C9C Br2C 118.1(6) . . ? C1D S1D C4D 90.8(5) . . ? C7D S2D C9D 90.2(5) . . ? C2D C1D S1D 114.8(8) . . ? C2D C1D Br1D 125.6(8) . . ? S1D C1D Br1D 119.6(6) . . ? C1D C2D C3D 108.1(9) . . ? C1D C2D H2D 126.0 . . ? C3D C2D H2D 126.0 . . ? C4D C3D C2D 115.9(10) . . ? C4D C3D C5D 108.6(9) . . ? C2D C3D C5D 135.4(10) . . ? C3D C4D C7D 110.1(10) . . ? C3D C4D S1D 110.4(8) . . ? C7D C4D S1D 139.5(8) . . ? O1D C5D C3D 127.5(10) . . ? O1D C5D C6D 127.9(10) . . ? C3D C5D C6D 104.6(9) . . ? C8D C6D C7D 115.2(10) . . ? C8D C6D C5D 137.3(10) . . ? C7D C6D C5D 107.5(9) . . ? C6D C7D C4D 109.2(9) . . ? C6D C7D S2D 111.6(8) . . ? C4D C7D S2D 139.2(8) . . ? C6D C8D C9D 109.6(9) . . ? C6D C8D H8D 125.2 . . ? C9D C8D H8D 125.2 . . ? C8D C9D S2D 113.5(8) . . ? C8D C9D Br2D 127.4(8) . . ? S2D C9D Br2D 119.1(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.126 _refine_diff_density_min -1.739 _refine_diff_density_rms 0.183 data_10 _database_code_depnum_ccdc_archive 'CCDC 914112' #TrackingRef '9a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-Bis-(pentafluorobenzoyl)-benzo[1,2-b:6,5-b'] dithiophene-4,5-bis-(ethyleneoxolane) ; _chemical_name_common ; 2,7-Bis-(pentafluorobenzoyl)-benzo[1,2-b:6,5-b'] dithiophene-4,5-bis-(ethyleneoxolane) ; _chemical_melting_point ? _chemical_formula_moiety 'C28 H10 F10 O6 S2' _chemical_formula_sum 'C28 H10 F10 O6 S2' _chemical_formula_weight 696.48 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' 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/c ' _symmetry_space_group_name_Hall -P2yc 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 7.9083(8) _cell_length_b 8.4393(8) _cell_length_c 19.2066(19) _cell_angle_alpha 90.00 _cell_angle_beta 92.076(2) _cell_angle_gamma 90.00 _cell_volume 1281.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2008 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 21.80 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.806 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.328 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6591 _exptl_absorpt_correction_T_max 0.7470 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3274 _diffrn_reflns_av_R_equivalents 0.0558 _diffrn_reflns_av_sigmaI/netI 0.1035 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2228 _reflns_number_gt 1072 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0110P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2228 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1061 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.0716 _refine_ls_wR_factor_gt 0.0593 _refine_ls_goodness_of_fit_ref 0.816 _refine_ls_restrained_S_all 0.816 _refine_ls_shift/su_max 0.002 _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 0.31056(11) -0.01184(11) 0.29550(6) 0.0465(3) Uani 1 1 d . . . F1 F -0.3113(2) -0.0059(3) 0.37492(13) 0.0770(8) Uani 1 1 d . . . F2 F -0.5175(3) 0.1556(3) 0.45581(14) 0.0987(10) Uani 1 1 d . . . F3 F -0.3917(3) 0.3707(3) 0.54727(15) 0.1024(10) Uani 1 1 d . . . F4 F -0.0545(3) 0.4158(3) 0.56196(14) 0.0792(8) Uani 1 1 d . . . F5 F 0.1547(3) 0.2538(2) 0.48348(12) 0.0642(7) Uani 1 1 d . . . O1 O 0.5546(3) 0.4611(3) 0.34302(13) 0.0470(7) Uani 1 1 d . . . O2 O 0.3336(3) 0.5746(3) 0.28376(14) 0.0452(7) Uani 1 1 d . . . O3 O 0.0144(3) -0.1105(3) 0.36959(15) 0.0632(9) Uani 1 1 d . . . C1 C 0.1721(4) 0.1081(4) 0.3396(2) 0.0386(10) Uani 1 1 d . . . C2 C 0.2133(4) 0.2650(4) 0.3329(2) 0.0416(10) Uani 1 1 d . . . H2 H 0.1522 0.3468 0.3525 0.050 Uiso 1 1 calc R . . C3 C 0.3572(4) 0.2896(4) 0.2934(2) 0.0355(9) Uani 1 1 d . . . C4 C 0.4249(4) 0.1498(4) 0.2696(2) 0.0384(10) Uani 1 1 d . . . C5 C 0.4475(4) 0.4450(4) 0.2830(2) 0.0387(10) Uani 1 1 d . . . C6 C 0.6632(4) 0.5979(4) 0.3404(2) 0.0561(12) Uani 1 1 d . . . H6A H 0.7344 0.6035 0.3825 0.067 Uiso 1 1 calc R . . H6B H 0.5953 0.6935 0.3374 0.067 Uiso 1 1 calc R . . C7 C 0.2295(4) 0.5860(4) 0.2214(2) 0.0575(13) Uani 1 1 d . . . H7A H 0.1575 0.6787 0.2238 0.069 Uiso 1 1 calc R . . H7B H 0.1575 0.4932 0.2171 0.069 Uiso 1 1 calc R . . C8 C 0.0323(4) 0.0305(4) 0.37533(19) 0.0362(9) Uani 1 1 d . . . C9 C -0.0684(5) 0.1226(4) 0.4219(2) 0.0430(10) Uani 1 1 d . . . C10 C -0.2440(5) 0.1017(5) 0.4201(2) 0.0561(13) Uani 1 1 d . . . C11 C -0.3514(5) 0.1816(6) 0.4608(3) 0.0640(14) Uani 1 1 d . . . C12 C -0.2890(5) 0.2902(6) 0.5072(2) 0.0609(13) Uani 1 1 d . . . C13 C -0.1196(6) 0.3141(5) 0.5140(2) 0.0546(12) Uani 1 1 d . . . C14 C -0.0139(5) 0.2308(5) 0.4721(2) 0.0477(11) 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 0.0527(6) 0.0337(5) 0.0540(7) -0.0013(5) 0.0143(5) -0.0047(5) F1 0.0549(15) 0.104(2) 0.0715(19) -0.0134(18) -0.0056(14) -0.0157(15) F2 0.0451(16) 0.162(3) 0.089(2) -0.002(2) 0.0057(16) 0.0013(17) F3 0.087(2) 0.134(3) 0.089(2) -0.020(2) 0.0288(19) 0.0325(18) F4 0.097(2) 0.0710(17) 0.070(2) -0.0172(16) 0.0121(16) -0.0002(15) F5 0.0481(14) 0.0790(17) 0.0655(19) -0.0111(14) 0.0026(13) -0.0124(12) O1 0.0489(16) 0.0442(16) 0.0476(19) -0.0054(14) -0.0014(14) -0.0060(13) O2 0.0459(17) 0.0342(14) 0.056(2) -0.0023(13) 0.0077(15) 0.0062(12) O3 0.0700(19) 0.0548(18) 0.066(2) -0.0012(17) 0.0161(17) -0.0120(15) C1 0.038(2) 0.039(2) 0.039(3) 0.0001(19) 0.007(2) 0.0032(18) C2 0.042(2) 0.042(2) 0.040(3) -0.003(2) 0.003(2) 0.0043(19) C3 0.037(2) 0.031(2) 0.040(3) -0.0004(18) 0.004(2) 0.0010(16) C4 0.039(2) 0.035(2) 0.041(3) -0.0008(19) 0.006(2) -0.0028(17) C5 0.040(3) 0.033(2) 0.044(3) -0.0021(18) 0.001(2) 0.0018(17) C6 0.046(3) 0.054(3) 0.068(4) -0.014(2) 0.001(3) -0.015(2) C7 0.037(3) 0.049(3) 0.086(4) 0.009(2) 0.001(3) 0.0071(19) C8 0.056(2) 0.024(2) 0.029(2) 0.0019(17) 0.007(2) -0.0052(18) C9 0.037(3) 0.047(2) 0.045(3) 0.010(2) -0.005(2) -0.0103(19) C10 0.062(3) 0.063(3) 0.043(3) -0.002(2) -0.013(3) -0.009(2) C11 0.031(3) 0.098(4) 0.063(4) -0.001(3) -0.003(3) 0.008(3) C12 0.048(3) 0.081(3) 0.056(4) 0.000(3) 0.016(3) 0.023(3) C13 0.069(3) 0.050(3) 0.044(3) -0.008(2) 0.004(3) 0.002(2) C14 0.032(2) 0.059(3) 0.052(3) 0.005(2) 0.005(2) -0.008(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 C4 1.720(3) . ? S1 C1 1.734(3) . ? F1 C10 1.351(4) . ? F2 C11 1.332(4) . ? F3 C12 1.326(4) . ? F4 C13 1.347(4) . ? F5 C14 1.357(4) . ? O1 C5 1.413(4) . ? O1 C6 1.441(4) . ? O2 C5 1.417(3) . ? O2 C7 1.431(4) . ? O3 C8 1.203(4) . ? C1 C2 1.371(4) . ? C1 C8 1.475(4) . ? C2 C3 1.406(4) . ? C2 H2 0.9300 . ? C3 C4 1.380(4) . ? C3 C5 1.510(4) . ? C4 C4 1.429(6) 2_655 ? C5 C5 1.540(7) 2_655 ? C6 C7 1.488(5) 2_655 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C6 1.488(5) 2_655 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.445(5) . ? C9 C14 1.385(5) . ? C9 C10 1.399(5) . ? C10 C11 1.355(5) . ? C11 C12 1.358(5) . ? C12 C13 1.357(5) . ? C13 C14 1.375(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 91.51(16) . . ? C5 O1 C6 112.9(3) . . ? C5 O2 C7 112.9(3) . . ? C2 C1 C8 131.1(3) . . ? C2 C1 S1 111.2(3) . . ? C8 C1 S1 117.7(2) . . ? C1 C2 C3 113.2(3) . . ? C1 C2 H2 123.4 . . ? C3 C2 H2 123.4 . . ? C4 C3 C2 112.6(3) . . ? C4 C3 C5 120.5(3) . . ? C2 C3 C5 126.6(3) . . ? C3 C4 C4 120.9(2) . 2_655 ? C3 C4 S1 111.6(3) . . ? C4 C4 S1 127.44(11) 2_655 . ? O1 C5 O2 106.2(3) . . ? O1 C5 C3 104.4(3) . . ? O2 C5 C3 111.4(3) . . ? O1 C5 C5 110.2(3) . 2_655 ? O2 C5 C5 111.8(3) . 2_655 ? C3 C5 C5 112.4(2) . 2_655 ? O1 C6 C7 109.3(3) . 2_655 ? O1 C6 H6A 109.8 . . ? C7 C6 H6A 109.8 2_655 . ? O1 C6 H6B 109.8 . . ? C7 C6 H6B 109.8 2_655 . ? H6A C6 H6B 108.3 . . ? O2 C7 C6 110.2(3) . 2_655 ? O2 C7 H7A 109.6 . . ? C6 C7 H7A 109.6 2_655 . ? O2 C7 H7B 109.6 . . ? C6 C7 H7B 109.6 2_655 . ? H7A C7 H7B 108.1 . . ? O3 C8 C9 121.5(3) . . ? O3 C8 C1 119.0(3) . . ? C9 C8 C1 119.2(3) . . ? C14 C9 C10 112.6(4) . . ? C14 C9 C8 128.4(4) . . ? C10 C9 C8 119.0(4) . . ? F1 C10 C11 117.6(4) . . ? F1 C10 C9 117.9(4) . . ? C11 C10 C9 124.4(4) . . ? F2 C11 C10 120.9(5) . . ? F2 C11 C12 119.5(4) . . ? C10 C11 C12 119.6(4) . . ? F3 C12 C13 119.4(5) . . ? F3 C12 C11 120.7(4) . . ? C13 C12 C11 119.8(4) . . ? F4 C13 C12 120.8(4) . . ? F4 C13 C14 120.1(4) . . ? C12 C13 C14 119.1(4) . . ? F5 C14 C13 116.5(4) . . ? F5 C14 C9 119.0(4) . . ? C13 C14 C9 124.4(4) . . ? _diffrn_measured_fraction_theta_max 0.883 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.883 _refine_diff_density_max 0.215 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.047 data_paul84 _database_code_depnum_ccdc_archive 'CCDC 914113' #TrackingRef 'S6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4'-Dibromo-2,2'-bis(4-hexyl-5-(trimethylsilyl)thiophen-2-yl)-5,5'-bithiazole ; _chemical_name_common ; 4,4'-Dibromo-2,2'-bis(4-hexyl-5-(trimethylsilyl)thiophen-2-yl)-5,5'-bithiazole ; _chemical_melting_point ? _chemical_formula_moiety 'C32 H46 Br2 N2 S4 Si2' _chemical_formula_sum 'C32 H46 Br2 N2 S4 Si2' _chemical_formula_weight 802.95 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc 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' '-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 37.478(2) _cell_length_b 7.0932(4) _cell_length_c 14.7217(8) _cell_angle_alpha 90.00 _cell_angle_beta 108.2470(10) _cell_angle_gamma 90.00 _cell_volume 3716.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5309 _cell_measurement_theta_min 2.2888 _cell_measurement_theta_max 28.1853 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 2.495 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3685 _exptl_absorpt_correction_T_max 0.6353 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20666 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -46 _diffrn_reflns_limit_h_max 46 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3652 _reflns_number_gt 3050 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_data_reduction 'SAINTPlus, v. 6.2 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0564P)^2^+6.2709P] 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 3652 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0982 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.244186(9) -0.20620(4) 0.20444(2) 0.02445(12) Uani 1 1 d . . . Si1 Si 0.38076(3) 0.78142(14) 0.20900(7) 0.0343(2) Uani 1 1 d . . . S1 S 0.27976(2) -0.00291(11) -0.03420(5) 0.02246(18) Uani 1 1 d . . . S2 S 0.32776(2) 0.43924(12) 0.17428(6) 0.0278(2) Uani 1 1 d . . . N1 N 0.27914(7) 0.0792(4) 0.13562(18) 0.0227(6) Uani 1 1 d . . . C1 C 0.25858(8) -0.1631(4) 0.0226(2) 0.0201(6) Uani 1 1 d . . . C2 C 0.26183(9) -0.0899(4) 0.1114(2) 0.0214(6) Uani 1 1 d . . . C3 C 0.29010(9) 0.1421(4) 0.0648(2) 0.0226(6) Uani 1 1 d . . . C4 C 0.31135(9) 0.3155(4) 0.0690(2) 0.0242(7) Uani 1 1 d . . . C5 C 0.32267(9) 0.3980(4) -0.0013(2) 0.0254(7) Uani 1 1 d . . . H5 H 0.3162 0.3508 -0.0647 0.030 Uiso 1 1 calc R . . C6 C 0.34516(9) 0.5615(5) 0.0299(2) 0.0267(7) Uani 1 1 d . . . C7 C 0.35096(9) 0.6013(5) 0.1252(2) 0.0281(7) Uani 1 1 d . . . C8 C 0.36220(10) 0.6700(5) -0.0344(3) 0.0308(7) Uani 1 1 d . . . H8A H 0.3592 0.8068 -0.0253 0.037 Uiso 1 1 calc R . . H8B H 0.3484 0.6393 -0.1019 0.037 Uiso 1 1 calc R . . C9 C 0.40385(10) 0.6256(6) -0.0144(3) 0.0381(9) Uani 1 1 d . . . H9A H 0.4065 0.4923 -0.0311 0.046 Uiso 1 1 calc R . . H9B H 0.4170 0.6411 0.0549 0.046 Uiso 1 1 calc R . . C10 C 0.42255(11) 0.7518(6) -0.0705(3) 0.0436(10) Uani 1 1 d . . . H10A H 0.4095 0.7343 -0.1398 0.052 Uiso 1 1 calc R . . H10B H 0.4193 0.8851 -0.0548 0.052 Uiso 1 1 calc R . . C11 C 0.46414(11) 0.7134(6) -0.0506(3) 0.0455(10) Uani 1 1 d . . . H11A H 0.4775 0.7413 0.0175 0.055 Uiso 1 1 calc R . . H11B H 0.4677 0.5778 -0.0612 0.055 Uiso 1 1 calc R . . C12 C 0.48162(12) 0.8280(7) -0.1122(4) 0.0562(12) Uani 1 1 d . . . H12A H 0.4796 0.9635 -0.0984 0.067 Uiso 1 1 calc R . . H12B H 0.4672 0.8065 -0.1803 0.067 Uiso 1 1 calc R . . C13 C 0.52265(13) 0.7805(8) -0.0966(4) 0.0722(16) Uani 1 1 d . . . H13A H 0.5374 0.8097 -0.0304 0.108 Uiso 1 1 calc R . . H13B H 0.5320 0.8552 -0.1404 0.108 Uiso 1 1 calc R . . H13C H 0.5250 0.6460 -0.1089 0.108 Uiso 1 1 calc R . . C14 C 0.42848(12) 0.6671(6) 0.2692(3) 0.0525(11) Uani 1 1 d . . . H14A H 0.4437 0.7504 0.3197 0.079 Uiso 1 1 calc R . . H14B H 0.4414 0.6460 0.2216 0.079 Uiso 1 1 calc R . . H14C H 0.4248 0.5461 0.2973 0.079 Uiso 1 1 calc R . . C15 C 0.38922(11) 0.9960(5) 0.1472(3) 0.0410(9) Uani 1 1 d . . . H15A H 0.3651 1.0499 0.1091 0.061 Uiso 1 1 calc R . . H15B H 0.4040 0.9632 0.1052 0.061 Uiso 1 1 calc R . . H15C H 0.4030 1.0885 0.1947 0.061 Uiso 1 1 calc R . . C16 C 0.35863(13) 0.8351(6) 0.3008(3) 0.0501(11) Uani 1 1 d . . . H16A H 0.3754 0.9150 0.3502 0.075 Uiso 1 1 calc R . . H16B H 0.3537 0.7175 0.3297 0.075 Uiso 1 1 calc R . . H16C H 0.3349 0.9016 0.2714 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0389(2) 0.02068(17) 0.02070(17) -0.00056(12) 0.01931(14) -0.00252(13) Si1 0.0432(6) 0.0316(5) 0.0281(5) -0.0036(4) 0.0114(4) -0.0165(4) S1 0.0315(4) 0.0201(4) 0.0213(4) 0.0002(3) 0.0163(3) -0.0022(3) S2 0.0359(5) 0.0260(4) 0.0250(4) -0.0014(3) 0.0145(3) -0.0063(3) N1 0.0303(14) 0.0214(13) 0.0207(13) 0.0006(10) 0.0142(11) -0.0009(11) C1 0.0252(16) 0.0174(14) 0.0225(15) 0.0032(12) 0.0142(12) 0.0016(12) C2 0.0297(16) 0.0193(14) 0.0210(15) 0.0017(12) 0.0162(13) 0.0008(13) C3 0.0286(16) 0.0199(15) 0.0223(15) -0.0011(13) 0.0121(13) 0.0005(13) C4 0.0289(16) 0.0202(16) 0.0273(16) -0.0002(13) 0.0142(14) 0.0007(13) C5 0.0316(17) 0.0229(16) 0.0267(16) -0.0013(13) 0.0165(14) 0.0005(13) C6 0.0279(17) 0.0263(17) 0.0299(17) 0.0042(14) 0.0146(14) 0.0003(13) C7 0.0329(18) 0.0239(17) 0.0317(18) 0.0000(14) 0.0160(14) -0.0032(14) C8 0.0331(18) 0.0308(18) 0.0329(18) 0.0050(14) 0.0165(15) -0.0036(14) C9 0.040(2) 0.037(2) 0.045(2) 0.0070(17) 0.0245(17) -0.0004(17) C10 0.041(2) 0.046(2) 0.050(2) 0.0051(19) 0.0239(19) -0.0042(18) C11 0.040(2) 0.052(3) 0.049(2) 0.0057(19) 0.0220(19) -0.0017(19) C12 0.049(3) 0.068(3) 0.061(3) 0.007(2) 0.032(2) -0.008(2) C13 0.047(3) 0.103(4) 0.077(4) 0.009(3) 0.034(3) -0.011(3) C14 0.045(2) 0.051(3) 0.053(3) 0.003(2) 0.003(2) -0.005(2) C15 0.042(2) 0.037(2) 0.046(2) -0.0042(17) 0.0184(18) -0.0048(17) C16 0.059(3) 0.054(3) 0.042(2) -0.011(2) 0.022(2) -0.019(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C2 1.887(3) . ? Si1 C16 1.833(4) . ? Si1 C15 1.850(4) . ? Si1 C7 1.881(3) . ? Si1 C14 1.910(4) . ? S1 C3 1.726(3) . ? S1 C1 1.742(3) . ? S2 C4 1.718(3) . ? S2 C7 1.730(3) . ? N1 C3 1.312(4) . ? N1 C2 1.357(4) . ? C1 C2 1.377(4) . ? C1 C1 1.451(6) 7_545 ? C3 C4 1.456(4) . ? C4 C5 1.367(4) . ? C5 C6 1.422(4) . ? C5 H5 0.9500 . ? C6 C7 1.381(4) . ? C6 C8 1.508(4) . ? C8 C9 1.528(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.530(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.518(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.512(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.520(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 C16 Si1 C15 112.2(2) . . ? C16 Si1 C7 108.16(17) . . ? C15 Si1 C7 113.23(17) . . ? C16 Si1 C14 108.7(2) . . ? C15 Si1 C14 107.33(19) . . ? C7 Si1 C14 107.05(18) . . ? C3 S1 C1 89.95(14) . . ? C4 S2 C7 92.73(15) . . ? C3 N1 C2 109.6(3) . . ? C2 C1 C1 130.5(3) . 7_545 ? C2 C1 S1 107.0(2) . . ? C1 C1 S1 122.5(3) 7_545 . ? N1 C2 C1 118.4(3) . . ? N1 C2 Br1 116.3(2) . . ? C1 C2 Br1 125.3(2) . . ? N1 C3 C4 123.8(3) . . ? N1 C3 S1 115.1(2) . . ? C4 C3 S1 121.0(2) . . ? C5 C4 C3 128.7(3) . . ? C5 C4 S2 110.8(2) . . ? C3 C4 S2 120.4(2) . . ? C4 C5 C6 113.5(3) . . ? C4 C5 H5 123.3 . . ? C6 C5 H5 123.3 . . ? C7 C6 C5 112.5(3) . . ? C7 C6 C8 124.8(3) . . ? C5 C6 C8 122.6(3) . . ? C6 C7 S2 110.4(2) . . ? C6 C7 Si1 132.7(3) . . ? S2 C7 Si1 116.75(18) . . ? C6 C8 C9 112.4(3) . . ? C6 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? C6 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? C8 C9 C10 112.8(3) . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 114.0(3) . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10B 108.8 . . ? C9 C10 H10B 108.8 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C10 113.5(4) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C11 C12 C13 113.5(4) . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? Si1 C14 H14A 109.5 . . ? Si1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? Si1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? Si1 C15 H15A 109.5 . . ? Si1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? Si1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? Si1 C16 H16A 109.5 . . ? Si1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? Si1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.435 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.084