# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_contact_author_name 'Peter Skabara' _publ_contact_author_address ; School of Chemistry The University of Manchester Oxford Road Manchester M13 9PL ; _publ_contact_author_email PETER.SKABARA@MANCHESTER.AC.UK _publ_section_title ;Hexyl-substituted oligothiophenes with a central terafluorophenylene unit: crystal engineering of planar structures for p-type organic semiconductors ; loop_ _publ_author_name 'Peter Skabara' 'Simon J. Coles' 'David J. Crouch' 'Martin J. Heeney' 'Michael B. Hursthouse' ; I.McCulloch ; data_5d _database_code_depnum_ccdc_archive 'CCDC 245177' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H58 F4 S4' _chemical_formula_weight 815.16 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1497(2) _cell_length_b 11.3722(8) _cell_length_c 15.4457(10) _cell_angle_alpha 91.678(3) _cell_angle_beta 97.587(4) _cell_angle_gamma 102.556(4) _cell_volume 1043.26(11) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 13995 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 434 _exptl_absorpt_coefficient_mu 0.278 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9090 _exptl_absorpt_correction_T_max 0.9890 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% negligible _diffrn_reflns_number 13381 _diffrn_reflns_av_R_equivalents 0.1914 _diffrn_reflns_av_sigmaI/netI 0.1194 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4477 _reflns_number_gt 3138 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Watkin, Pearce 1995)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1901P)^2^+0.6554P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.050(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4477 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1293 _refine_ls_R_factor_gt 0.0839 _refine_ls_wR_factor_ref 0.3113 _refine_ls_wR_factor_gt 0.2350 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.002 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 C1 C -0.0788(7) 0.4753(4) 0.0762(3) 0.0232(9) Uani 1 1 d . . . C2 C 0.1351(7) 0.5439(4) 0.0757(3) 0.0228(9) Uani 1 1 d . . . C3 C 0.2259(7) 0.5724(4) -0.0009(3) 0.0236(9) Uani 1 1 d . . . C4 C 0.4547(8) 0.6464(4) -0.0020(3) 0.0237(9) Uani 1 1 d . . . C5 C 0.5601(8) 0.6792(3) -0.0732(3) 0.0248(9) Uani 1 1 d . . . H5 H 0.4915 0.6547 -0.1316 0.030 Uiso 1 1 calc R . . C6 C 0.7782(8) 0.7521(4) -0.0527(3) 0.0244(9) Uani 1 1 d . . . C7 C 0.8415(8) 0.7766(4) 0.0372(3) 0.0237(9) Uani 1 1 d . . . C8 C 0.9300(8) 0.7982(4) -0.1197(3) 0.0269(10) Uani 1 1 d . . . H8A H 1.0755 0.7747 -0.1041 0.032 Uiso 1 1 calc R . . H8B H 0.9606 0.8875 -0.1165 0.032 Uiso 1 1 calc R . . C9 C 0.8356(9) 0.7522(4) -0.2136(3) 0.0307(10) Uani 1 1 d . . . H9A H 0.8016 0.6629 -0.2173 0.037 Uiso 1 1 calc R . . H9B H 0.6929 0.7780 -0.2306 0.037 Uiso 1 1 calc R . . C10 C 0.9980(9) 0.7987(5) -0.2774(3) 0.0334(11) Uani 1 1 d . . . H10A H 1.1416 0.7743 -0.2595 0.040 Uiso 1 1 calc R . . H10B H 1.0300 0.8880 -0.2742 0.040 Uiso 1 1 calc R . . C11 C 0.9085(11) 0.7521(5) -0.3718(3) 0.0489(15) Uani 1 1 d . B . H11A H 0.8790 0.6628 -0.3751 0.059 Uiso 1 1 calc R . . H11B H 0.7636 0.7753 -0.3893 0.059 Uiso 1 1 calc R . . C12 C 1.0696(11) 0.8002(5) -0.4361(3) 0.0480(14) Uani 1 1 d . . . H12A H 0.9874 0.7863 -0.4964 0.058 Uiso 1 1 calc R A 1 H12B H 1.1262 0.8883 -0.4241 0.058 Uiso 1 1 calc R A 1 C13 C 1.252(2) 0.7441(13) -0.4300(7) 0.061(4) Uani 0.520(13) 1 d P B 1 H13A H 1.3638 0.7858 -0.4650 0.092 Uiso 0.520(13) 1 calc PR B 1 H13B H 1.1994 0.6596 -0.4520 0.092 Uiso 0.520(13) 1 calc PR B 1 H13C H 1.3207 0.7478 -0.3687 0.092 Uiso 0.520(13) 1 calc PR B 1 C13' C 1.044(2) 0.9203(10) -0.4606(7) 0.047(3) Uani 0.480(13) 1 d P B 2 H13D H 1.0871 0.9766 -0.4088 0.071 Uiso 0.480(13) 1 calc PR B 2 H13E H 0.8869 0.9166 -0.4846 0.071 Uiso 0.480(13) 1 calc PR B 2 H13F H 1.1411 0.9482 -0.5048 0.071 Uiso 0.480(13) 1 calc PR B 2 C14 C 1.0435(8) 0.8470(4) 0.0885(3) 0.0264(10) Uani 1 1 d . . . C15 C 1.0904(9) 0.8630(4) 0.1786(3) 0.0331(11) Uani 1 1 d . . . H15 H 0.9893 0.8261 0.2165 0.040 Uiso 1 1 calc R . . C16 C 1.3009(9) 0.9386(4) 0.2088(3) 0.0330(11) Uani 1 1 d . . . C17 C 1.4142(9) 0.9811(4) 0.1423(3) 0.0310(10) Uani 1 1 d . . . H17 H 1.5593 1.0335 0.1506 0.037 Uiso 1 1 calc R . . C18 C 1.3935(10) 0.9708(5) 0.3054(3) 0.0429(13) Uani 1 1 d . . . H18A H 1.5484 1.0207 0.3099 0.051 Uiso 1 1 calc R . . H18B H 1.3002 1.0200 0.3306 0.051 Uiso 1 1 calc R . . C19 C 1.3979(12) 0.8609(7) 0.3593(3) 0.0574(17) Uani 1 1 d . . . H19A H 1.4574 0.8896 0.4208 0.069 Uiso 1 1 calc R . . H19B H 1.2411 0.8149 0.3582 0.069 Uiso 1 1 calc R . . C20 C 1.5328(14) 0.7773(7) 0.3307(3) 0.066(2) Uani 1 1 d . D . H20A H 1.4794 0.7542 0.2679 0.080 Uiso 1 1 calc R . . H20B H 1.6906 0.8234 0.3350 0.080 Uiso 1 1 calc R . . C21 C 1.5351(19) 0.6668(9) 0.3754(5) 0.092(3) Uani 1 1 d . . . H21A H 1.3848 0.6446 0.3945 0.110 Uiso 1 1 calc R C 1 H21B H 1.6426 0.6929 0.4296 0.110 Uiso 1 1 calc R C 1 C22 C 1.582(3) 0.5475(14) 0.3462(13) 0.079(7) Uani 0.460(18) 1 d P D 1 H22A H 1.5095 0.5220 0.2855 0.094 Uiso 0.460(18) 1 calc PR D 1 H22B H 1.5289 0.4833 0.3854 0.094 Uiso 0.460(18) 1 calc PR D 1 C23 C 1.845(4) 0.5779(15) 0.3529(10) 0.068(6) Uani 0.460(18) 1 d P D 1 H23A H 1.8925 0.6454 0.3166 0.102 Uiso 0.460(18) 1 calc PR D 1 H23B H 1.8942 0.5071 0.3323 0.102 Uiso 0.460(18) 1 calc PR D 1 H23C H 1.9113 0.6003 0.4139 0.102 Uiso 0.460(18) 1 calc PR D 1 C22' C 1.700(4) 0.6015(17) 0.3414(8) 0.063(5) Uani 0.540(18) 1 d P D 2 H22C H 1.6548 0.5810 0.2779 0.076 Uiso 0.540(18) 1 calc PR D 2 H22D H 1.8521 0.6550 0.3502 0.076 Uiso 0.540(18) 1 calc PR D 2 C23' C 1.704(3) 0.4876(12) 0.3888(9) 0.069(5) Uani 0.540(18) 1 d P D 2 H23D H 1.7407 0.5077 0.4519 0.104 Uiso 0.540(18) 1 calc PR D 2 H23E H 1.8178 0.4490 0.3690 0.104 Uiso 0.540(18) 1 calc PR D 2 H23F H 1.5558 0.4322 0.3763 0.104 Uiso 0.540(18) 1 calc PR D 2 F1 F -0.1429(5) 0.4547(2) 0.15613(15) 0.0304(7) Uani 1 1 d . . . F2 F 0.2567(5) 0.5816(2) 0.15416(15) 0.0325(7) Uani 1 1 d . . . S1 S 0.6263(2) 0.70687(9) 0.09331(6) 0.0250(4) Uani 1 1 d . . . S2 S 1.2663(2) 0.92963(10) 0.04203(7) 0.0290(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 C1 0.028(2) 0.023(2) 0.0223(19) 0.0053(15) 0.0088(16) 0.0110(18) C2 0.022(2) 0.0213(19) 0.0225(18) -0.0011(15) -0.0017(15) 0.0036(17) C3 0.031(3) 0.018(2) 0.0225(19) 0.0016(15) 0.0013(17) 0.0095(18) C4 0.033(3) 0.021(2) 0.0211(18) 0.0008(15) 0.0024(16) 0.0134(18) C5 0.034(3) 0.0171(19) 0.0235(19) 0.0019(15) 0.0012(17) 0.0082(18) C6 0.033(3) 0.0192(19) 0.0224(19) 0.0005(15) 0.0003(16) 0.0103(18) C7 0.031(2) 0.020(2) 0.0214(18) 0.0026(15) 0.0008(16) 0.0090(17) C8 0.034(3) 0.025(2) 0.022(2) 0.0031(16) 0.0031(17) 0.0075(19) C9 0.038(3) 0.033(2) 0.0198(19) -0.0001(17) 0.0033(17) 0.007(2) C10 0.040(3) 0.037(3) 0.022(2) -0.0006(18) 0.0060(18) 0.007(2) C11 0.059(4) 0.053(3) 0.027(2) -0.006(2) 0.006(2) -0.004(3) C12 0.066(4) 0.052(3) 0.025(2) 0.002(2) 0.008(2) 0.011(3) C13 0.074(10) 0.079(9) 0.038(6) 0.011(6) 0.012(6) 0.029(8) C13' 0.076(9) 0.043(6) 0.026(5) 0.012(4) 0.010(5) 0.016(6) C14 0.038(3) 0.019(2) 0.023(2) -0.0001(15) -0.0011(17) 0.0106(18) C15 0.043(3) 0.031(2) 0.025(2) 0.0052(17) 0.0048(19) 0.006(2) C16 0.036(3) 0.034(2) 0.026(2) -0.0029(18) -0.0024(18) 0.008(2) C17 0.030(3) 0.028(2) 0.033(2) -0.0010(18) 0.0023(18) 0.0035(19) C18 0.047(3) 0.049(3) 0.028(2) -0.006(2) -0.001(2) 0.006(3) C19 0.066(4) 0.082(5) 0.027(2) -0.002(3) 0.002(2) 0.027(4) C20 0.092(6) 0.086(5) 0.026(3) -0.011(3) -0.008(3) 0.043(4) C21 0.132(8) 0.114(7) 0.048(4) 0.004(4) -0.012(4) 0.085(7) C22 0.054(11) 0.037(8) 0.112(14) 0.030(8) -0.054(9) -0.024(7) C23 0.090(15) 0.049(9) 0.060(9) -0.011(7) -0.011(9) 0.020(9) C22' 0.086(14) 0.069(11) 0.044(6) 0.008(6) 0.003(7) 0.037(10) C23' 0.088(11) 0.057(8) 0.076(9) 0.022(7) 0.020(8) 0.037(8) F1 0.0334(16) 0.0383(15) 0.0184(11) 0.0031(10) 0.0055(10) 0.0043(12) F2 0.0394(17) 0.0370(15) 0.0176(11) 0.0001(10) 0.0007(10) 0.0027(12) S1 0.0316(7) 0.0240(6) 0.0198(5) 0.0019(4) 0.0022(4) 0.0077(4) S2 0.0346(7) 0.0266(6) 0.0246(6) 0.0021(4) 0.0025(4) 0.0050(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 C1 F1 1.356(5) . ? C1 C2 1.377(6) . ? C1 C3 1.393(6) 2_565 ? C2 F2 1.342(5) . ? C2 C3 1.391(6) . ? C3 C1 1.393(6) 2_565 ? C3 C4 1.477(7) . ? C4 C5 1.370(6) . ? C4 S1 1.723(4) . ? C5 C6 1.405(6) . ? C5 H5 0.9500 . ? C6 C7 1.394(6) . ? C6 C8 1.515(6) . ? C7 C14 1.443(7) . ? C7 S1 1.738(5) . ? C8 C9 1.521(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.519(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.525(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.525(8) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.401(14) . ? C12 C13' 1.463(12) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C13' H13D 0.9800 . ? C13' H13E 0.9800 . ? C13' H13F 0.9800 . ? C14 C15 1.382(6) . ? C14 S2 1.736(5) . ? C15 C16 1.402(7) . ? C15 H15 0.9500 . ? C16 C17 1.359(7) . ? C16 C18 1.528(6) . ? C17 S2 1.706(5) . ? C17 H17 0.9500 . ? C18 C19 1.524(8) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.484(9) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.454(11) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22' 1.514(18) . ? C21 C22 1.51(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.57(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C22' C23' 1.51(2) . ? C22' H22C 0.9900 . ? C22' H22D 0.9900 . ? C23' H23D 0.9800 . ? C23' H23E 0.9800 . ? C23' H23F 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 F1 C1 C2 116.1(4) . . ? F1 C1 C3 120.1(4) . 2_565 ? C2 C1 C3 123.8(4) . 2_565 ? F2 C2 C1 116.4(4) . . ? F2 C2 C3 120.6(4) . . ? C1 C2 C3 123.0(4) . . ? C2 C3 C1 113.2(4) . 2_565 ? C2 C3 C4 123.3(4) . . ? C1 C3 C4 123.5(4) 2_565 . ? C5 C4 C3 128.0(4) . . ? C5 C4 S1 110.5(4) . . ? C3 C4 S1 121.4(3) . . ? C4 C5 C6 114.4(4) . . ? C4 C5 H5 122.8 . . ? C6 C5 H5 122.8 . . ? C7 C6 C5 112.3(4) . . ? C7 C6 C8 123.3(4) . . ? C5 C6 C8 124.4(4) . . ? C6 C7 C14 132.4(4) . . ? C6 C7 S1 110.2(4) . . ? C14 C7 S1 117.4(3) . . ? C6 C8 C9 114.7(4) . . ? C6 C8 H8A 108.6 . . ? C9 C8 H8A 108.6 . . ? C6 C8 H8B 108.6 . . ? C9 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? C10 C9 C8 112.3(4) . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C9 C10 C11 113.2(4) . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10B 108.9 . . ? C11 C10 H10B 108.9 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 113.3(5) . . ? 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 . . ? C13 C12 C13' 132.7(10) . . ? C13 C12 C11 111.6(7) . . ? C13' C12 C11 110.1(7) . . ? C13 C12 H12A 109.3 . . ? C13' C12 H12A 76.0 . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12B 109.3 . . ? C13' C12 H12B 34.1 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? C12 C13' H13D 109.5 . . ? C12 C13' H13E 109.5 . . ? H13D C13' H13E 109.5 . . ? C12 C13' H13F 109.5 . . ? H13D C13' H13F 109.5 . . ? H13E C13' H13F 109.5 . . ? C15 C14 C7 127.4(5) . . ? C15 C14 S2 109.6(4) . . ? C7 C14 S2 123.0(3) . . ? C14 C15 C16 113.8(5) . . ? C14 C15 H15 123.1 . . ? C16 C15 H15 123.1 . . ? C17 C16 C15 112.3(4) . . ? C17 C16 C18 123.4(5) . . ? C15 C16 C18 124.3(5) . . ? C16 C17 S2 112.4(4) . . ? C16 C17 H17 123.8 . . ? S2 C17 H17 123.8 . . ? C19 C18 C16 113.5(5) . . ? C19 C18 H18A 108.9 . . ? C16 C18 H18A 108.9 . . ? C19 C18 H18B 108.9 . . ? C16 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? C20 C19 C18 115.9(5) . . ? C20 C19 H19A 108.3 . . ? C18 C19 H19A 108.3 . . ? C20 C19 H19B 108.3 . . ? C18 C19 H19B 108.3 . . ? H19A C19 H19B 107.4 . . ? C21 C20 C19 119.4(7) . . ? C21 C20 H20A 107.5 . . ? C19 C20 H20A 107.5 . . ? C21 C20 H20B 107.5 . . ? C19 C20 H20B 107.5 . . ? H20A C20 H20B 107.0 . . ? C20 C21 C22' 110.4(10) . . ? C20 C21 C22 131.7(10) . . ? C22' C21 C22 32.8(8) . . ? C20 C21 H21A 104.3 . . ? C22' C21 H21A 137.1 . . ? C22 C21 H21A 104.3 . . ? C20 C21 H21B 104.3 . . ? C22' C21 H21B 89.7 . . ? C22 C21 H21B 104.3 . . ? H21A C21 H21B 105.6 . . ? C21 C22 C23 102.3(12) . . ? C21 C22 H22A 111.3 . . ? C23 C22 H22A 111.3 . . ? C21 C22 H22B 111.3 . . ? C23 C22 H22B 111.3 . . ? H22A C22 H22B 109.2 . . ? C23' C22' C21 110.2(13) . . ? C23' C22' H22C 109.6 . . ? C21 C22' H22C 109.6 . . ? C23' C22' H22D 109.6 . . ? C21 C22' H22D 109.6 . . ? H22C C22' H22D 108.1 . . ? C22' C23' H23D 109.5 . . ? C22' C23' H23E 109.5 . . ? H23D C23' H23E 109.5 . . ? C22' C23' H23F 109.5 . . ? H23D C23' H23F 109.5 . . ? H23E C23' H23F 109.5 . . ? C4 S1 C7 92.5(2) . . ? C17 S2 C14 92.0(2) . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.919 _refine_diff_density_min -1.500 _refine_diff_density_rms 0.173 data_5b _database_code_depnum_ccdc_archive 'CCDC 245178' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H34 F4 S4' _chemical_formula_weight 646.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1250 0.1230 '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(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x+1/2, z+1/4' '-x, -y, z+1/2' 'y+1/2, -x+1/2, z+3/4' 'x+1/2, -y+1/2, -z+3/4' 'y, x, -z' '-x+1/2, y+1/2, -z+1/4' '-y, -x, -z+1/2' _cell_length_a 20.5113(12) _cell_length_b 20.5113(12) _cell_length_c 14.2496(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5995.0(7) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 224411 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.1 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2704 _exptl_absorpt_coefficient_mu 0.366 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9643 _exptl_absorpt_correction_T_max 0.9855 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruiker-Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% negligible _diffrn_reflns_number 59088 _diffrn_reflns_av_R_equivalents 0.2283 _diffrn_reflns_av_sigmaI/netI 0.1407 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.08 _reflns_number_total 6585 _reflns_number_gt 4093 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1212P)^2^+42.8855P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0057(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(3) _refine_ls_number_reflns 6585 _refine_ls_number_parameters 382 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.2061 _refine_ls_R_factor_gt 0.1388 _refine_ls_wR_factor_ref 0.3407 _refine_ls_wR_factor_gt 0.3069 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.158 _refine_ls_shift/su_mean 0.040 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 0.64483(12) 0.15178(13) 0.1479(2) 0.0423(8) Uani 1 1 d . . . S2 S 0.70136(14) -0.05330(16) 0.1482(3) 0.0533(9) Uani 1 1 d . . . S3 S 0.35605(12) 0.42722(13) 0.1156(2) 0.0374(7) Uani 1 1 d . . . S4 S 0.29877(18) 0.63026(16) 0.0997(4) 0.0696(12) Uani 1 1 d . . . F1 F 0.4230(3) 0.1836(3) 0.1420(6) 0.057(2) Uani 1 1 d . . . F2 F 0.3709(3) 0.2960(3) 0.1339(6) 0.053(2) Uani 1 1 d . . . F3 F 0.5767(3) 0.3958(3) 0.1357(6) 0.058(2) Uani 1 1 d . . . F4 F 0.6317(3) 0.2831(3) 0.1467(6) 0.0552(19) Uani 1 1 d . . . C1 C 0.5591(5) 0.1601(5) 0.1486(9) 0.039(3) Uani 1 1 d . . . C2 C 0.5296(5) 0.1018(5) 0.1442(8) 0.032(2) Uani 1 1 d . . . H2 H 0.4836 0.0973 0.1405 0.038 Uiso 1 1 calc R . . C3 C 0.5743(6) 0.0450(5) 0.1457(9) 0.044(3) Uani 1 1 d . . . C4 C 0.6379(5) 0.0684(5) 0.1433(9) 0.039(3) Uani 1 1 d . . . C5 C 0.7002(5) 0.0319(5) 0.1401(7) 0.030(2) Uani 1 1 d . . . C6 C 0.7640(4) 0.0573(5) 0.1317(7) 0.027(2) Uani 1 1 d . . . H6 H 0.7745 0.1024 0.1285 0.033 Uiso 1 1 calc R . . C7 C 0.8089(5) 0.0068(5) 0.1289(8) 0.037(3) Uani 1 1 d . . . H7 H 0.8545 0.0137 0.1219 0.045 Uiso 1 1 calc R . . C8 C 0.7819(6) -0.0539(6) 0.1373(9) 0.048(3) Uani 1 1 d . . . H8 H 0.8069 -0.0929 0.1369 0.057 Uiso 1 1 calc R . . C9 C 0.5533(5) -0.0228(5) 0.1457(9) 0.041(3) Uani 1 1 d . . . H9A H 0.5732 -0.0447 0.2006 0.050 Uiso 1 1 calc R . . H9B H 0.5711 -0.0440 0.0887 0.050 Uiso 1 1 calc R . . C10 C 0.4796(6) -0.0354(5) 0.1485(10) 0.047(3) Uani 1 1 d . . . H10A H 0.4606 -0.0129 0.2035 0.056 Uiso 1 1 calc R . . H10B H 0.4593 -0.0171 0.0913 0.056 Uiso 1 1 calc R . . C11 C 0.4648(5) -0.1062(5) 0.1543(10) 0.043(3) Uani 1 1 d . . . H11A H 0.4843 -0.1247 0.2120 0.052 Uiso 1 1 calc R . . H11B H 0.4837 -0.1291 0.0996 0.052 Uiso 1 1 calc R . . C12 C 0.3883(6) -0.1164(5) 0.1561(10) 0.049(3) Uani 1 1 d . . . H12A H 0.3703 -0.0952 0.2128 0.058 Uiso 1 1 calc R . . H12B H 0.3690 -0.0947 0.1006 0.058 Uiso 1 1 calc R . . C13 C 0.3685(6) -0.1877(6) 0.1559(10) 0.051(3) Uani 1 1 d . . . H13A H 0.3902 -0.2108 0.2083 0.061 Uiso 1 1 calc R . . H13B H 0.3821 -0.2085 0.0963 0.061 Uiso 1 1 calc R . . C14 C 0.2946(8) -0.1921(7) 0.1667(10) 0.069(4) Uani 1 1 d . . . H14A H 0.2840 -0.2093 0.2291 0.104 Uiso 1 1 calc R . . H14B H 0.2769 -0.2212 0.1185 0.104 Uiso 1 1 calc R . . H14C H 0.2755 -0.1486 0.1596 0.104 Uiso 1 1 calc R . . C15 C 0.5291(4) 0.2245(4) 0.1403(8) 0.031(2) Uani 1 1 d . . . C16 C 0.4640(5) 0.2367(4) 0.1393(10) 0.045(3) Uani 1 1 d . . . C17 C 0.4355(5) 0.2950(6) 0.1329(8) 0.041(3) Uani 1 1 d . . . C18 C 0.4696(5) 0.3507(5) 0.1353(8) 0.038(3) Uani 1 1 d . . . C19 C 0.5376(6) 0.3428(6) 0.1390(9) 0.047(3) Uani 1 1 d . . . C20 C 0.5668(4) 0.2833(4) 0.1448(8) 0.031(2) Uani 1 1 d . . . C21 C 0.4419(6) 0.4184(5) 0.1239(8) 0.040(3) Uani 1 1 d . . . C22 C 0.4675(5) 0.4793(5) 0.1292(8) 0.042(3) Uani 1 1 d . . . H22 H 0.5128 0.4861 0.1387 0.051 Uiso 1 1 calc R . . C23 C 0.4248(4) 0.5309(4) 0.1203(7) 0.027(2) Uani 1 1 d . . . C24 C 0.3605(4) 0.5098(4) 0.1147(7) 0.028(2) Uani 1 1 d U . . C25 C 0.3026(4) 0.5487(5) 0.1046(8) 0.031(2) Uani 1 1 d . . . C26 C 0.2335(4) 0.5162(4) 0.1040(7) 0.025(2) Uani 1 1 d U . . H26 H 0.2228 0.4714 0.1111 0.029 Uiso 1 1 calc R . . C27 C 0.1898(6) 0.5711(6) 0.0901(9) 0.047(3) Uani 1 1 d . . . H27 H 0.1444 0.5654 0.0798 0.056 Uiso 1 1 calc R . . C28 C 0.2172(6) 0.6295(6) 0.0927(12) 0.065(4) Uani 1 1 d . . . H28 H 0.1922 0.6685 0.0906 0.079 Uiso 1 1 calc R . . C29 C 0.4450(4) 0.6011(5) 0.1225(9) 0.035(3) Uani 1 1 d . . . H29A H 0.4254 0.6219 0.1785 0.041 Uiso 1 1 calc R . . H29B H 0.4269 0.6231 0.0664 0.041 Uiso 1 1 calc R . . C30 C 0.5176(5) 0.6122(5) 0.1247(9) 0.038(3) Uani 1 1 d . . . H30A H 0.5373 0.5944 0.0666 0.046 Uiso 1 1 calc R . . H30B H 0.5365 0.5885 0.1787 0.046 Uiso 1 1 calc R . . C31 C 0.5348(5) 0.6862(5) 0.1330(9) 0.038(3) Uani 1 1 d . . . H31A H 0.5151 0.7104 0.0799 0.045 Uiso 1 1 calc R . . H31B H 0.5167 0.7040 0.1921 0.045 Uiso 1 1 calc R . . C32 C 0.6080(5) 0.6948(5) 0.1319(9) 0.038(3) Uani 1 1 d . . . H32A H 0.6267 0.6661 0.1808 0.046 Uiso 1 1 calc R . . H32B H 0.6244 0.6792 0.0706 0.046 Uiso 1 1 calc R . . C33 C 0.6338(5) 0.7619(6) 0.1473(10) 0.046(3) Uani 1 1 d . . . H33A H 0.6147 0.7913 0.0996 0.055 Uiso 1 1 calc R . . H33B H 0.6191 0.7774 0.2097 0.055 Uiso 1 1 calc R . . C34 C 0.7059(6) 0.7674(5) 0.1428(14) 0.082(6) Uani 1 1 d . . . H34A H 0.7255 0.7382 0.1893 0.123 Uiso 1 1 calc R . . H34B H 0.7189 0.8124 0.1561 0.123 Uiso 1 1 calc R . . H34C H 0.7208 0.7551 0.0799 0.123 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 0.0266(13) 0.0284(13) 0.072(2) 0.0046(14) -0.0013(14) -0.0014(11) S2 0.0303(15) 0.0526(19) 0.077(2) 0.0102(17) 0.0084(16) 0.0065(13) S3 0.0265(13) 0.0348(13) 0.0509(17) 0.0047(13) 0.0038(12) 0.0023(10) S4 0.057(2) 0.0377(18) 0.114(3) -0.005(2) -0.009(2) 0.0075(15) F1 0.035(3) 0.033(3) 0.104(6) 0.002(4) 0.009(4) -0.006(3) F2 0.028(3) 0.014(3) 0.115(6) -0.001(4) -0.003(4) -0.007(2) F3 0.024(3) 0.031(3) 0.117(7) -0.007(4) 0.006(4) 0.004(3) F4 0.024(3) 0.037(4) 0.104(6) 0.003(4) 0.001(4) -0.002(3) C1 0.018(5) 0.036(6) 0.063(8) 0.014(6) 0.013(5) 0.012(4) C2 0.021(5) 0.038(6) 0.037(6) 0.001(5) 0.006(5) 0.001(4) C3 0.057(7) 0.029(6) 0.045(7) 0.002(5) 0.004(6) 0.003(5) C4 0.042(6) 0.025(5) 0.050(7) 0.009(5) 0.000(6) -0.004(5) C5 0.032(5) 0.039(6) 0.018(5) -0.007(4) 0.001(4) -0.007(4) C6 0.015(4) 0.040(5) 0.027(5) -0.014(4) 0.005(4) 0.007(4) C7 0.023(5) 0.038(6) 0.051(8) -0.010(5) -0.013(5) 0.005(4) C8 0.052(7) 0.042(6) 0.049(8) -0.004(6) -0.012(6) -0.007(5) C9 0.035(6) 0.036(6) 0.054(8) 0.007(6) -0.012(5) -0.012(5) C10 0.059(7) 0.022(5) 0.061(8) 0.007(6) 0.000(7) -0.011(5) C11 0.025(5) 0.025(5) 0.080(9) -0.011(6) 0.004(6) 0.006(4) C12 0.052(7) 0.035(6) 0.059(8) 0.023(6) 0.008(6) 0.000(5) C13 0.056(8) 0.047(7) 0.048(8) -0.002(6) -0.013(6) -0.002(6) C14 0.083(11) 0.060(9) 0.065(9) 0.029(7) -0.017(8) -0.030(8) C15 0.022(5) 0.022(5) 0.049(7) 0.010(5) 0.001(5) -0.006(4) C16 0.040(6) 0.011(4) 0.085(9) 0.000(5) -0.012(6) 0.016(4) C17 0.018(5) 0.063(8) 0.042(7) -0.001(6) -0.011(5) 0.013(5) C18 0.038(6) 0.030(5) 0.044(7) 0.001(5) 0.004(5) 0.020(5) C19 0.048(7) 0.045(7) 0.048(7) 0.013(6) -0.004(6) -0.019(5) C20 0.014(4) 0.013(4) 0.067(7) -0.011(5) -0.009(5) 0.004(3) C21 0.066(7) 0.018(5) 0.036(7) 0.012(5) 0.015(6) -0.002(5) C22 0.041(6) 0.030(5) 0.057(8) 0.013(5) 0.026(6) 0.016(5) C23 0.030(5) 0.019(4) 0.032(6) -0.003(4) 0.020(4) 0.010(4) C24 0.028(2) 0.027(2) 0.028(2) -0.0002(10) 0.0000(10) 0.0010(10) C25 0.021(5) 0.024(5) 0.047(6) -0.010(5) 0.000(5) 0.002(4) C26 0.024(2) 0.025(2) 0.025(2) 0.0001(10) -0.0001(10) 0.0010(10) C27 0.041(7) 0.055(8) 0.044(7) -0.002(6) -0.011(5) 0.008(6) C28 0.039(7) 0.037(7) 0.121(13) -0.009(8) -0.006(8) 0.027(5) C29 0.013(4) 0.044(6) 0.047(7) 0.006(5) -0.011(5) 0.003(4) C30 0.033(6) 0.035(6) 0.048(7) -0.012(5) 0.000(5) 0.007(4) C31 0.039(6) 0.021(5) 0.053(7) 0.011(5) 0.001(6) 0.007(4) C32 0.036(6) 0.024(5) 0.054(8) 0.010(5) -0.007(6) -0.006(4) C33 0.038(6) 0.050(7) 0.051(7) 0.003(6) -0.015(6) -0.025(5) C34 0.042(7) 0.017(5) 0.187(18) 0.045(9) 0.012(10) 0.014(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 S1 C4 1.717(10) . ? S1 C1 1.766(10) . ? S2 C8 1.659(12) . ? S2 C5 1.751(10) . ? S3 C24 1.695(9) . ? S3 C21 1.774(12) . ? S4 C28 1.676(13) . ? S4 C25 1.676(10) . ? F1 C16 1.377(12) . ? F2 C17 1.324(11) . ? F3 C19 1.351(12) . ? F4 C20 1.332(10) . ? C1 C2 1.342(15) . ? C1 C15 1.461(13) . ? C2 C3 1.483(14) . ? C3 C4 1.390(16) . ? C3 C9 1.458(14) . ? C4 C5 1.482(15) . ? C5 C6 1.412(13) . ? C6 C7 1.389(13) . ? C7 C8 1.369(15) . ? C9 C10 1.533(15) . ? C10 C11 1.486(14) . ? C11 C12 1.582(15) . ? C12 C13 1.518(15) . ? C13 C14 1.527(19) . ? C15 C16 1.358(14) . ? C15 C20 1.435(12) . ? C16 C17 1.334(14) . ? C17 C18 1.339(16) . ? C18 C19 1.406(15) . ? C18 C21 1.510(13) . ? C19 C20 1.362(15) . ? C21 C22 1.355(15) . ? C22 C23 1.379(13) . ? C23 C24 1.390(13) . ? C23 C29 1.498(14) . ? C24 C25 1.440(13) . ? C25 C26 1.566(13) . ? C26 C27 1.452(14) . ? C27 C28 1.324(18) . ? C29 C30 1.506(13) . ? C30 C31 1.563(13) . ? C31 C32 1.512(14) . ? C32 C33 1.491(14) . ? C33 C34 1.484(16) . ? 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 90.9(5) . . ? C8 S2 C5 90.9(5) . . ? C24 S3 C21 92.8(5) . . ? C28 S4 C25 92.3(6) . . ? C2 C1 C15 127.6(9) . . ? C2 C1 S1 111.3(7) . . ? C15 C1 S1 120.5(7) . . ? C1 C2 C3 114.8(9) . . ? C4 C3 C9 127.4(10) . . ? C4 C3 C2 108.0(9) . . ? C9 C3 C2 124.6(10) . . ? C3 C4 C5 129.5(9) . . ? C3 C4 S1 114.8(8) . . ? C5 C4 S1 115.7(7) . . ? C6 C5 C4 127.9(9) . . ? C6 C5 S2 111.2(7) . . ? C4 C5 S2 120.9(7) . . ? C7 C6 C5 109.9(9) . . ? C6 C7 C8 114.1(10) . . ? C7 C8 S2 113.9(9) . . ? C3 C9 C10 116.9(10) . . ? C11 C10 C9 111.6(9) . . ? C10 C11 C12 109.5(9) . . ? C13 C12 C11 113.1(9) . . ? C12 C13 C14 108.8(10) . . ? C16 C15 C20 112.0(8) . . ? C16 C15 C1 125.6(8) . . ? C20 C15 C1 121.9(8) . . ? C17 C16 C15 126.7(10) . . ? C17 C16 F1 116.3(9) . . ? C15 C16 F1 117.0(8) . . ? F2 C17 C18 120.6(10) . . ? F2 C17 C16 116.9(11) . . ? C18 C17 C16 122.2(9) . . ? C17 C18 C19 114.9(9) . . ? C17 C18 C21 125.9(10) . . ? C19 C18 C21 118.8(10) . . ? F3 C19 C20 117.5(10) . . ? F3 C19 C18 119.7(10) . . ? C20 C19 C18 122.8(9) . . ? F4 C20 C19 116.4(8) . . ? F4 C20 C15 122.5(8) . . ? C19 C20 C15 120.9(8) . . ? C22 C21 C18 134.1(11) . . ? C22 C21 S3 107.1(8) . . ? C18 C21 S3 118.3(8) . . ? C21 C22 C23 117.1(10) . . ? C22 C23 C24 111.6(9) . . ? C22 C23 C29 124.0(9) . . ? C24 C23 C29 124.3(8) . . ? C23 C24 C25 128.0(9) . . ? C23 C24 S3 111.2(7) . . ? C25 C24 S3 120.7(7) . . ? C24 C25 C26 120.7(8) . . ? C24 C25 S4 126.6(7) . . ? C26 C25 S4 112.5(7) . . ? C27 C26 C25 103.2(8) . . ? C28 C27 C26 115.9(10) . . ? C27 C28 S4 115.6(9) . . ? C23 C29 C30 114.8(8) . . ? C29 C30 C31 111.8(8) . . ? C32 C31 C30 109.7(8) . . ? C33 C32 C31 117.3(9) . . ? C34 C33 C32 114.6(10) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.08 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.734 _refine_diff_density_min -0.828 _refine_diff_density_rms 0.152