# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Todd Marder' 'Lucas Applegarth' 'A. Batsanov' 'A. Beeby' 'Abdou Boucekkine' 'Jonathan C. Collings' 'Karine Costuas' 'J. Halet' 'J. Howard' 'Laurent Porres' 'Simon R. Rutter' 'Jamie S. Siddle' 'Amber L. Thompson' 'Richard M. Ward' _publ_contact_author_name 'Todd Marder' _publ_contact_author_address ; Department of Chemistry Durham University South Road Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email TODD.MARDER@DURHAM.AC.UK _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Synthesis, photophysical properties and crystal and molecular structures of luminescent 2,5-bis(p-R-phenylethynyl)thiophenes and 2,5-bis(pentafluorophenylethynyl)thiophene ; data_(1a) _database_code_depnum_ccdc_archive 'CCDC 641166' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,5-bis(phenylethynyl)thiophene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H12 S' _chemical_formula_sum 'C20 H12 S' _chemical_formula_weight 284.36 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' 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 'P 21/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 14.752(1) _cell_length_b 5.7461(2) _cell_length_c 17.339(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.87(1) _cell_angle_gamma 90.00 _cell_volume 1469.60(14) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2228 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 27.42 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.209 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9398 _exptl_absorpt_correction_T_max 0.9958 _exptl_absorpt_process_details 'SADABS (G.M.Sheldrick, 1998)' _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal Space, by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (30s exposure) covering 0.3\% in \w. Crystal to detector distance 4.42 cm. ; _diffrn_ambient_temperature 120(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 'Siemens SMART 1K CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 9126 _diffrn_reflns_av_R_equivalents 0.0674 _diffrn_reflns_av_sigmaI/netI 0.0832 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3365 _reflns_number_gt 2098 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART-NT V5.049 (Bruker, 1998)' _computing_cell_refinement 'SAINT version 6.02A (Bruker, 2001)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 6.12 (Bruker, 2001)' _computing_publication_material 'SHELXTL version 6.12 (Bruker, 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. ; _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^)+(0.0557P)^2^+0.0887P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 3365 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1032 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1272 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 0.17771(4) 0.10828(12) 0.92394(4) 0.02375(19) Uani 1 1 d . . . C2 C 0.08714(17) 0.1715(5) 0.86254(14) 0.0217(6) Uani 1 1 d . . . C3 C 0.01815(18) 0.0128(5) 0.87153(15) 0.0278(6) Uani 1 1 d . . . H3 H -0.0394(18) 0.020(5) 0.8419(15) 0.029(7) Uiso 1 1 d . . . C4 C 0.03784(18) -0.1601(5) 0.92702(15) 0.0260(6) Uani 1 1 d . . . H4 H -0.0028(19) -0.281(6) 0.9420(16) 0.040(8) Uiso 1 1 d . . . C5 C 0.12256(16) -0.1325(4) 0.96084(14) 0.0198(5) Uani 1 1 d . . . C6 C 0.09288(16) 0.3535(5) 0.80720(14) 0.0214(6) Uani 1 1 d . . . C7 C 0.09956(16) 0.4972(5) 0.75681(14) 0.0217(6) Uani 1 1 d . . . C8 C 0.16655(16) -0.2747(5) 1.01703(14) 0.0210(6) Uani 1 1 d . . . C9 C 0.20814(16) -0.3925(5) 1.06243(14) 0.0202(5) Uani 1 1 d . . . C11 C 0.10829(16) 0.6618(4) 0.69469(14) 0.0209(6) Uani 1 1 d . . . C12 C 0.16007(16) 0.8649(5) 0.70421(15) 0.0231(6) Uani 1 1 d . . . H12 H 0.1911(18) 0.906(5) 0.7512(15) 0.027(7) Uiso 1 1 d . . . C13 C 0.16802(18) 1.0231(5) 0.64401(15) 0.0238(6) Uani 1 1 d . . . H13 H 0.2004(19) 1.180(5) 0.6502(15) 0.034(8) Uiso 1 1 d . . . C14 C 0.12467(17) 0.9799(5) 0.57340(15) 0.0259(6) Uani 1 1 d . . . H14 H 0.1319(18) 1.097(5) 0.5319(16) 0.031(8) Uiso 1 1 d . . . C15 C 0.07443(17) 0.7778(5) 0.56310(15) 0.0257(6) Uani 1 1 d . . . H15 H 0.0426(17) 0.741(5) 0.5163(15) 0.024(7) Uiso 1 1 d . . . C16 C 0.06597(17) 0.6183(5) 0.62282(14) 0.0236(6) Uani 1 1 d . . . H16 H 0.0285(18) 0.480(5) 0.6189(14) 0.026(7) Uiso 1 1 d . . . C21 C 0.26149(16) -0.5409(4) 1.11266(13) 0.0187(5) Uani 1 1 d . . . C22 C 0.34980(17) -0.4768(5) 1.13566(14) 0.0204(5) Uani 1 1 d . . . H22 H 0.3743(18) -0.338(5) 1.1180(16) 0.033(8) Uiso 1 1 d . . . C23 C 0.40173(17) -0.6240(5) 1.18164(14) 0.0238(6) Uani 1 1 d . . . H23 H 0.4638(17) -0.586(5) 1.1970(13) 0.018(6) Uiso 1 1 d . . . C24 C 0.36626(18) -0.8353(5) 1.20675(15) 0.0251(6) Uani 1 1 d . . . H24 H 0.4003(19) -0.931(5) 1.2400(16) 0.034(8) Uiso 1 1 d . . . C25 C 0.27877(18) -0.9001(5) 1.18429(15) 0.0234(6) Uani 1 1 d . . . H25 H 0.2558(18) -1.047(5) 1.2032(15) 0.032(8) Uiso 1 1 d . . . C26 C 0.22689(17) -0.7556(5) 1.13754(14) 0.0210(6) Uani 1 1 d . . . H26 H 0.1640(18) -0.796(5) 1.1225(15) 0.029(7) Uiso 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 0.0239(3) 0.0243(4) 0.0229(3) 0.0041(3) -0.0050(2) -0.0028(3) C2 0.0228(12) 0.0248(15) 0.0174(12) -0.0006(10) -0.0009(10) 0.0060(11) C3 0.0211(13) 0.0373(17) 0.0248(14) 0.0069(13) -0.0021(11) 0.0007(13) C4 0.0230(13) 0.0301(17) 0.0249(14) 0.0063(12) -0.0004(11) -0.0055(12) C5 0.0205(12) 0.0199(14) 0.0190(12) 0.0013(11) 0.0009(9) 0.0002(11) C6 0.0201(12) 0.0257(15) 0.0185(12) -0.0005(11) -0.0010(9) 0.0015(11) C7 0.0218(12) 0.0234(14) 0.0196(13) -0.0023(11) -0.0021(10) 0.0025(12) C8 0.0234(13) 0.0202(14) 0.0196(13) -0.0015(11) 0.0017(10) -0.0008(11) C9 0.0211(12) 0.0189(13) 0.0206(13) -0.0012(11) 0.0019(10) -0.0021(11) C11 0.0181(12) 0.0224(15) 0.0222(13) 0.0019(11) -0.0004(10) 0.0049(11) C12 0.0195(12) 0.0255(15) 0.0243(14) -0.0032(12) -0.0021(10) 0.0047(12) C13 0.0251(13) 0.0193(14) 0.0272(14) -0.0001(11) 0.0036(11) 0.0016(12) C14 0.0261(14) 0.0272(15) 0.0246(14) 0.0078(12) 0.0062(11) 0.0052(13) C15 0.0228(13) 0.0321(16) 0.0220(14) 0.0016(12) -0.0032(11) 0.0043(13) C16 0.0220(13) 0.0251(15) 0.0238(13) 0.0008(12) -0.0010(10) -0.0014(13) C21 0.0223(12) 0.0193(14) 0.0145(12) -0.0017(10) 0.0015(9) 0.0008(11) C22 0.0221(13) 0.0188(13) 0.0205(13) 0.0015(11) 0.0036(10) -0.0019(12) C23 0.0184(12) 0.0312(16) 0.0216(13) -0.0003(12) -0.0013(10) -0.0002(12) C24 0.0263(14) 0.0286(16) 0.0205(13) 0.0012(12) 0.0014(11) 0.0078(12) C25 0.0291(14) 0.0197(14) 0.0216(13) 0.0047(12) 0.0014(10) -0.0002(13) C26 0.0175(13) 0.0225(14) 0.0229(13) 0.0000(11) -0.0005(10) -0.0012(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 C5 1.732(3) . ? S1 C2 1.734(3) . ? C2 C3 1.377(4) . ? C2 C6 1.423(4) . ? C3 C4 1.410(4) . ? C3 H3 0.99(3) . ? C4 C5 1.382(4) . ? C4 H4 0.96(3) . ? C5 C8 1.421(3) . ? C6 C7 1.207(4) . ? C7 C11 1.441(4) . ? C8 C9 1.200(3) . ? C9 C21 1.444(3) . ? C11 C12 1.403(4) . ? C11 C16 1.408(3) . ? C12 C13 1.391(4) . ? C12 H12 0.96(3) . ? C13 C14 1.395(4) . ? C13 H13 1.03(3) . ? C14 C15 1.388(4) . ? C14 H14 0.99(3) . ? C15 C16 1.390(4) . ? C15 H15 0.95(3) . ? C16 H16 0.97(3) . ? C21 C26 1.406(4) . ? C21 C22 1.406(3) . ? C22 C23 1.386(4) . ? C22 H22 0.93(3) . ? C23 C24 1.394(4) . ? C23 H23 0.98(2) . ? C24 C25 1.393(4) . ? C24 H24 0.94(3) . ? C25 C26 1.383(4) . ? C25 H25 0.97(3) . ? C26 H26 0.99(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 C5 S1 C2 91.84(12) . . ? C3 C2 C6 127.9(2) . . ? C3 C2 S1 110.8(2) . . ? C6 C2 S1 121.0(2) . . ? C2 C3 C4 113.5(2) . . ? C2 C3 H3 122.9(17) . . ? C4 C3 H3 123.6(17) . . ? C5 C4 C3 112.6(2) . . ? C5 C4 H4 122.3(18) . . ? C3 C4 H4 125.0(18) . . ? C4 C5 C8 128.7(2) . . ? C4 C5 S1 111.2(2) . . ? C8 C5 S1 120.02(18) . . ? C7 C6 C2 175.7(3) . . ? C6 C7 C11 177.9(3) . . ? C9 C8 C5 176.4(3) . . ? C8 C9 C21 176.1(3) . . ? C12 C11 C16 119.0(2) . . ? C12 C11 C7 120.8(2) . . ? C16 C11 C7 120.1(2) . . ? C13 C12 C11 120.5(2) . . ? C13 C12 H12 115.6(17) . . ? C11 C12 H12 123.9(17) . . ? C12 C13 C14 120.0(3) . . ? C12 C13 H13 122.8(16) . . ? C14 C13 H13 117.0(16) . . ? C15 C14 C13 119.9(3) . . ? C15 C14 H14 122.5(16) . . ? C13 C14 H14 117.6(17) . . ? C14 C15 C16 120.7(3) . . ? C14 C15 H15 123.4(17) . . ? C16 C15 H15 115.9(17) . . ? C15 C16 C11 119.9(3) . . ? C15 C16 H16 123.1(15) . . ? C11 C16 H16 116.8(15) . . ? C26 C21 C22 118.8(2) . . ? C26 C21 C9 120.4(2) . . ? C22 C21 C9 120.7(2) . . ? C23 C22 C21 120.3(2) . . ? C23 C22 H22 120.0(17) . . ? C21 C22 H22 119.6(17) . . ? C22 C23 C24 120.3(2) . . ? C22 C23 H23 121.8(16) . . ? C24 C23 H23 117.8(16) . . ? C25 C24 C23 119.7(3) . . ? C25 C24 H24 120.0(18) . . ? C23 C24 H24 120.2(18) . . ? C26 C25 C24 120.3(3) . . ? C26 C25 H25 121.9(17) . . ? C24 C25 H25 117.7(17) . . ? C25 C26 C21 120.4(2) . . ? C25 C26 H26 121.5(17) . . ? C21 C26 H26 118.0(17) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.311 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.064 #============================================END data_(1b) _database_code_depnum_ccdc_archive 'CCDC 641167' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,5-bis(p-methylphenylethynyl)thiophene ; _chemical_name_common ? _chemical_melting_point 441.3(2) _chemical_formula_moiety 'C22 H16 S' _chemical_formula_sum 'C22 H16 S' _chemical_formula_weight 312.41 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' 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 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.0717(15) _cell_length_b 5.0902(5) _cell_length_c 21.2336(19) _cell_angle_alpha 90.00 _cell_angle_beta 112.217(10) _cell_angle_gamma 90.00 _cell_volume 1608.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5758 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 29.00 _exptl_crystal_description prism _exptl_crystal_colour 'light brown' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 4 runs of narrow-frame \w-scans (scan width 0.3\% \w, 10s exposure), every run at a different \f angle. Crystal to detector distance 4.45 cm. ; _diffrn_ambient_temperature 120(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 'Siemens SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 17948 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 29.00 _reflns_number_total 4255 _reflns_number_gt 3243 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.049 (Bruker, 1998)' _computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)' _computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. ; _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^)+(0.0449P)^2^+0.7678P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4255 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.45063(3) 0.91711(8) 0.23334(2) 0.02171(11) Uani 1 1 d . . . C2 C 0.52393(10) 1.0970(3) 0.20831(8) 0.0207(3) Uani 1 1 d . . . C3 C 0.51632(12) 1.0262(4) 0.14365(9) 0.0262(4) Uani 1 1 d . . . H3 H 0.5533(13) 1.106(4) 0.1225(10) 0.029(5) Uiso 1 1 d . . . C4 C 0.45182(12) 0.8292(4) 0.11490(9) 0.0259(4) Uani 1 1 d . . . H4 H 0.4373(14) 0.759(4) 0.0700(11) 0.038(6) Uiso 1 1 d . . . C5 C 0.40971(11) 0.7482(3) 0.15721(8) 0.0203(3) Uani 1 1 d . . . C6 C 0.58067(11) 1.2895(3) 0.25284(8) 0.0214(3) Uani 1 1 d . . . C7 C 0.62661(11) 1.4485(3) 0.29063(8) 0.0211(3) Uani 1 1 d . . . C8 C 0.34203(11) 0.5550(3) 0.14575(8) 0.0220(3) Uani 1 1 d . . . C9 C 0.28599(11) 0.3939(3) 0.13813(8) 0.0207(3) Uani 1 1 d . . . C10 C 0.85960(13) 2.2149(4) 0.47319(10) 0.0284(4) Uani 1 1 d . . . H101 H 0.8554(15) 2.210(5) 0.5175(12) 0.048(6) Uiso 1 1 d . . . H102 H 0.9239(16) 2.180(4) 0.4794(11) 0.045(6) Uiso 1 1 d . . . H103 H 0.8471(16) 2.387(5) 0.4544(12) 0.051(7) Uiso 1 1 d . . . C11 C 0.68423(11) 1.6423(3) 0.33608(8) 0.0199(3) Uani 1 1 d . . . C12 C 0.67575(12) 1.7019(4) 0.39762(9) 0.0248(4) Uani 1 1 d . . . H12 H 0.6306(13) 1.613(4) 0.4087(10) 0.032(5) Uiso 1 1 d . . . C13 C 0.73271(12) 1.8849(3) 0.44190(9) 0.0253(4) Uani 1 1 d . . . H13 H 0.7274(13) 1.920(4) 0.4855(10) 0.033(5) Uiso 1 1 d . . . C14 C 0.79826(11) 2.0148(3) 0.42577(8) 0.0214(3) Uani 1 1 d . . . C15 C 0.80553(11) 1.9565(3) 0.36386(8) 0.0231(4) Uani 1 1 d . . . H15 H 0.8497(14) 2.043(4) 0.3512(10) 0.035(6) Uiso 1 1 d . . . C16 C 0.74986(12) 1.7731(3) 0.31965(8) 0.0222(3) Uani 1 1 d . . . H16 H 0.7565(13) 1.737(4) 0.2770(10) 0.031(5) Uiso 1 1 d . . . C20 C 0.00475(12) -0.3718(4) 0.09202(9) 0.0250(4) Uani 1 1 d . . . H201 H -0.0364(13) -0.363(4) 0.0457(11) 0.034(5) Uiso 1 1 d . . . H202 H -0.0297(14) -0.337(4) 0.1196(10) 0.035(5) Uiso 1 1 d . . . H203 H 0.0297(13) -0.551(4) 0.1035(10) 0.031(5) Uiso 1 1 d . . . C21 C 0.21708(11) 0.1981(3) 0.12767(8) 0.0199(3) Uani 1 1 d . . . C22 C 0.18748(12) 0.1286(3) 0.17949(8) 0.0234(4) Uani 1 1 d . . . H22 H 0.2144(13) 0.210(4) 0.2235(10) 0.032(5) Uiso 1 1 d . . . C23 C 0.11938(12) -0.0537(3) 0.16767(8) 0.0236(4) Uani 1 1 d . . . H23 H 0.0988(13) -0.090(4) 0.2048(10) 0.031(5) Uiso 1 1 d . . . C24 C 0.07843(11) -0.1739(3) 0.10446(8) 0.0205(3) Uani 1 1 d . . . C25 C 0.10907(12) -0.1061(4) 0.05326(8) 0.0250(4) Uani 1 1 d . . . H25 H 0.0837(13) -0.186(4) 0.0094(10) 0.031(5) Uiso 1 1 d . . . C26 C 0.17698(11) 0.0751(3) 0.06426(8) 0.0239(3) Uani 1 1 d . . . H26 H 0.1984(12) 0.117(4) 0.0274(10) 0.026(5) Uiso 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 0.0222(2) 0.0217(2) 0.0222(2) -0.00204(16) 0.00947(16) -0.00295(17) C2 0.0169(7) 0.0185(8) 0.0257(8) 0.0008(6) 0.0069(6) -0.0003(6) C3 0.0253(9) 0.0298(9) 0.0254(8) -0.0022(7) 0.0120(7) -0.0078(7) C4 0.0278(9) 0.0288(9) 0.0215(8) -0.0040(7) 0.0100(7) -0.0068(7) C5 0.0186(8) 0.0192(8) 0.0201(7) 0.0001(6) 0.0038(6) -0.0002(6) C6 0.0189(8) 0.0219(8) 0.0253(8) 0.0030(7) 0.0105(7) 0.0032(7) C7 0.0206(8) 0.0232(8) 0.0220(8) 0.0027(7) 0.0108(7) 0.0042(7) C8 0.0221(8) 0.0224(8) 0.0200(7) 0.0024(6) 0.0062(6) 0.0042(7) C9 0.0196(8) 0.0235(8) 0.0165(7) -0.0003(6) 0.0039(6) 0.0030(7) C10 0.0287(10) 0.0254(10) 0.0274(9) -0.0056(8) 0.0066(8) -0.0029(8) C11 0.0185(8) 0.0173(8) 0.0224(8) 0.0005(6) 0.0062(6) 0.0023(6) C12 0.0239(9) 0.0263(9) 0.0269(9) -0.0032(7) 0.0128(7) -0.0033(7) C13 0.0283(9) 0.0258(9) 0.0235(8) -0.0028(7) 0.0119(7) 0.0004(7) C14 0.0209(8) 0.0179(8) 0.0236(8) -0.0013(6) 0.0063(7) 0.0033(6) C15 0.0220(8) 0.0232(9) 0.0249(8) 0.0002(7) 0.0097(7) -0.0008(7) C16 0.0241(9) 0.0231(8) 0.0205(8) -0.0012(6) 0.0096(7) -0.0002(7) C20 0.0234(9) 0.0249(9) 0.0249(9) 0.0013(7) 0.0070(7) -0.0045(7) C21 0.0184(8) 0.0175(8) 0.0218(8) 0.0021(6) 0.0053(6) 0.0009(6) C22 0.0264(9) 0.0230(9) 0.0187(8) -0.0024(6) 0.0062(7) -0.0030(7) C23 0.0266(9) 0.0246(9) 0.0212(8) 0.0005(7) 0.0109(7) -0.0022(7) C24 0.0196(8) 0.0181(7) 0.0227(8) 0.0014(6) 0.0066(6) 0.0001(6) C25 0.0264(9) 0.0281(9) 0.0191(8) -0.0031(7) 0.0072(7) -0.0049(7) C26 0.0238(8) 0.0278(9) 0.0204(8) -0.0004(7) 0.0087(7) -0.0041(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 C5 1.7266(16) . ? S1 C2 1.7268(17) . ? C2 C3 1.379(2) . ? C2 C6 1.426(2) . ? C3 C4 1.405(2) . ? C3 H3 0.959(19) . ? C4 C5 1.377(2) . ? C4 H4 0.96(2) . ? C5 C8 1.418(2) . ? C6 C7 1.182(2) . ? C7 C11 1.444(2) . ? C8 C9 1.183(2) . ? C9 C21 1.443(2) . ? C10 C14 1.507(2) . ? C10 H101 0.97(2) . ? C10 H102 1.01(2) . ? C10 H103 0.95(2) . ? C11 C12 1.398(2) . ? C11 C16 1.398(2) . ? C12 C13 1.392(2) . ? C12 H12 0.96(2) . ? C13 C14 1.392(2) . ? C13 H13 0.98(2) . ? C14 C15 1.395(2) . ? C15 C16 1.385(2) . ? C15 H15 0.96(2) . ? C16 H16 0.968(19) . ? C20 C24 1.500(2) . ? C20 H201 0.96(2) . ? C20 H202 0.96(2) . ? C20 H203 0.99(2) . ? C21 C22 1.399(2) . ? C21 C26 1.401(2) . ? C22 C23 1.384(2) . ? C22 H22 0.96(2) . ? C23 C24 1.393(2) . ? C23 H23 0.98(2) . ? C24 C25 1.396(2) . ? C25 C26 1.380(2) . ? C25 H25 0.95(2) . ? C26 H26 0.989(19) . ? 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 C5 S1 C2 92.21(8) . . ? C3 C2 C6 129.29(15) . . ? C3 C2 S1 110.72(12) . . ? C6 C2 S1 119.99(12) . . ? C2 C3 C4 113.09(15) . . ? C2 C3 H3 121.2(12) . . ? C4 C3 H3 125.7(12) . . ? C5 C4 C3 113.21(15) . . ? C5 C4 H4 122.8(13) . . ? C3 C4 H4 124.0(12) . . ? C4 C5 C8 129.09(15) . . ? C4 C5 S1 110.77(12) . . ? C8 C5 S1 120.14(12) . . ? C7 C6 C2 178.53(17) . . ? C6 C7 C11 178.69(17) . . ? C9 C8 C5 178.10(17) . . ? C8 C9 C21 179.07(17) . . ? C14 C10 H101 111.4(14) . . ? C14 C10 H102 110.4(13) . . ? H101 C10 H102 108.4(18) . . ? C14 C10 H103 111.1(14) . . ? H101 C10 H103 110(2) . . ? H102 C10 H103 105.0(19) . . ? C12 C11 C16 118.63(15) . . ? C12 C11 C7 120.57(15) . . ? C16 C11 C7 120.80(14) . . ? C13 C12 C11 120.33(16) . . ? C13 C12 H12 121.2(12) . . ? C11 C12 H12 118.5(12) . . ? C14 C13 C12 121.14(16) . . ? C14 C13 H13 119.4(12) . . ? C12 C13 H13 119.5(12) . . ? C13 C14 C15 118.16(15) . . ? C13 C14 C10 121.41(15) . . ? C15 C14 C10 120.43(16) . . ? C16 C15 C14 121.27(16) . . ? C16 C15 H15 118.6(12) . . ? C14 C15 H15 120.2(12) . . ? C15 C16 C11 120.46(15) . . ? C15 C16 H16 119.4(12) . . ? C11 C16 H16 120.2(12) . . ? C24 C20 H201 110.0(12) . . ? C24 C20 H202 111.6(12) . . ? H201 C20 H202 106.5(17) . . ? C24 C20 H203 110.9(11) . . ? H201 C20 H203 110.8(17) . . ? H202 C20 H203 106.9(17) . . ? C22 C21 C26 118.24(15) . . ? C22 C21 C9 121.50(15) . . ? C26 C21 C9 120.25(14) . . ? C23 C22 C21 120.51(15) . . ? C23 C22 H22 120.0(12) . . ? C21 C22 H22 119.5(12) . . ? C22 C23 C24 121.49(15) . . ? C22 C23 H23 117.6(11) . . ? C24 C23 H23 120.8(11) . . ? C23 C24 C25 117.69(15) . . ? C23 C24 C20 121.23(15) . . ? C25 C24 C20 121.08(15) . . ? C26 C25 C24 121.51(16) . . ? C26 C25 H25 117.9(12) . . ? C24 C25 H25 120.5(12) . . ? C25 C26 C21 120.55(15) . . ? C25 C26 H26 119.9(11) . . ? C21 C26 H26 119.5(11) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.353 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.053 #============================================END data_(1h) _database_code_depnum_ccdc_archive 'CCDC 641168' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,5-bis(p-carbomethoxyphenylethynyl)thiophene ; _chemical_name_common ? _chemical_melting_point 475.2(5) _chemical_formula_moiety 'C24 H16 O4 S' _chemical_formula_sum 'C24 H16 O4 S' _chemical_formula_weight 400.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P c a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 7.1798(8) _cell_length_b 45.453(4) _cell_length_c 5.8879(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1921.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8364 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 29.00 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.197 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 4 runs of narrow-frame \w-scans (scan width 0.3\% \w, 10s exposure), every run at a different \f angle. Crystal to detector distance 6.84 cm. 2790 unique reflections after merging Friedel equivalents. ; _diffrn_ambient_temperature 120(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 6K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 5.6 _diffrn_standards_number 0 _diffrn_reflns_number 19478 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -61 _diffrn_reflns_limit_k_max 61 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 29.00 _reflns_number_total 4881 _reflns_number_gt 4505 _reflns_threshold_expression I>2\s(I) _reflns_Friedel_coverage 0.75 _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)' _computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. ; _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^)+(0.0599P)^2^+1.1378P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _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 0.21(8) _refine_ls_number_reflns 4881 _refine_ls_number_parameters 326 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1159 _refine_ls_wR_factor_gt 0.1135 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.56841(7) 0.753880(10) 0.53558(11) 0.02119(12) Uani 1 1 d . . . O1 O 0.5685(2) 0.55773(3) -0.2820(3) 0.0222(3) Uani 1 1 d . . . O2 O 0.4358(2) 0.53784(3) 0.0262(4) 0.0282(3) Uani 1 1 d . . . O3 O 0.4359(2) 0.94247(3) 1.4647(3) 0.0255(4) Uani 1 1 d . . . O4 O 0.5553(3) 0.96093(3) 1.1418(3) 0.0311(4) Uani 1 1 d . . . C2 C 0.5021(3) 0.71856(4) 0.6064(4) 0.0195(4) Uani 1 1 d . . . C3 C 0.4287(3) 0.71721(5) 0.8232(4) 0.0199(4) Uani 1 1 d . . . H3 H 0.384(3) 0.6996(6) 0.895(5) 0.019(6) Uiso 1 1 d . . . C4 C 0.4237(3) 0.74481(5) 0.9296(4) 0.0206(4) Uani 1 1 d . . . H4 H 0.380(4) 0.7497(6) 1.078(6) 0.026(7) Uiso 1 1 d . . . C5 C 0.4931(3) 0.76708(5) 0.7956(4) 0.0194(4) Uani 1 1 d . . . C6 C 0.5126(3) 0.69443(5) 0.4540(4) 0.0225(4) Uani 1 1 d . . . C7 C 0.5057(3) 0.67254(5) 0.3380(4) 0.0201(4) Uani 1 1 d . . . C8 C 0.5074(3) 0.79720(5) 0.8544(4) 0.0226(4) Uani 1 1 d . . . C9 C 0.5115(3) 0.82235(5) 0.9188(4) 0.0218(4) Uani 1 1 d . . . C10 C 0.4988(3) 0.55881(4) -0.0717(4) 0.0180(4) Uani 1 1 d . . . C11 C 0.5002(3) 0.64485(4) 0.2238(4) 0.0168(4) Uani 1 1 d . . . C12 C 0.5766(3) 0.64074(4) 0.0069(4) 0.0179(4) Uani 1 1 d . . . H12 H 0.623(4) 0.6573(6) -0.070(4) 0.022(7) Uiso 1 1 d . . . C13 C 0.5789(3) 0.61295(5) -0.0906(4) 0.0165(4) Uani 1 1 d . . . H13 H 0.625(3) 0.6105(5) -0.242(4) 0.011(6) Uiso 1 1 d . . . C14 C 0.5039(3) 0.58909(4) 0.0268(4) 0.0162(4) Uani 1 1 d . . . C15 C 0.4258(3) 0.59313(5) 0.2412(4) 0.0176(4) Uani 1 1 d . . . H15 H 0.382(4) 0.5772(6) 0.317(5) 0.025(7) Uiso 1 1 d . . . C16 C 0.4235(3) 0.62070(5) 0.3384(4) 0.0183(4) Uani 1 1 d . . . H6 H 0.368(3) 0.6233(5) 0.484(4) 0.014(6) Uiso 1 1 d . . . C17 C 0.5580(4) 0.52899(5) -0.3900(5) 0.0256(5) Uani 1 1 d . . . H171 H 0.595(4) 0.5307(7) -0.551(6) 0.030(8) Uiso 1 1 d . . . H172 H 0.633(4) 0.5146(7) -0.309(6) 0.043(8) Uiso 1 1 d . . . H173 H 0.431(4) 0.5232(6) -0.419(5) 0.031(8) Uiso 1 1 d . . . C20 C 0.4982(3) 0.94038(5) 1.2519(4) 0.0199(4) Uani 1 1 d . . . C21 C 0.5088(3) 0.85178(4) 1.0022(4) 0.0198(4) Uani 1 1 d . . . C22 C 0.5779(3) 0.87535(5) 0.8702(4) 0.0195(4) Uani 1 1 d . . . H22 H 0.631(3) 0.8709(5) 0.730(5) 0.015(6) Uiso 1 1 d . . . C23 C 0.5707(3) 0.90374(5) 0.9538(4) 0.0193(4) Uani 1 1 d . . . H23 H 0.621(4) 0.9215(6) 0.859(5) 0.031(7) Uiso 1 1 d . . . C24 C 0.4954(3) 0.90942(4) 1.1669(4) 0.0174(4) Uani 1 1 d . . . C25 C 0.4243(3) 0.88640(4) 1.2974(4) 0.0185(4) Uani 1 1 d . . . H25 H 0.368(4) 0.8907(6) 1.436(5) 0.034(8) Uiso 1 1 d . . . C26 C 0.4308(3) 0.85763(4) 1.2151(4) 0.0199(4) Uani 1 1 d . . . H26 H 0.389(4) 0.8429(6) 1.307(5) 0.021(7) Uiso 1 1 d . . . C27 C 0.4478(4) 0.97189(5) 1.5628(5) 0.0288(5) Uani 1 1 d . . . H271 H 0.362(4) 0.9849(6) 1.478(5) 0.036(8) Uiso 1 1 d . . . H272 H 0.577(4) 0.9781(6) 1.562(6) 0.027(7) Uiso 1 1 d . . . H273 H 0.415(4) 0.9702(7) 1.721(6) 0.044(9) Uiso 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 0.0234(2) 0.0192(2) 0.0209(3) -0.0037(2) 0.0034(2) -0.00195(17) O1 0.0298(9) 0.0174(7) 0.0192(8) -0.0055(6) 0.0038(7) -0.0021(6) O2 0.0417(9) 0.0175(6) 0.0254(8) -0.0001(8) 0.0072(8) -0.0047(6) O3 0.0365(9) 0.0169(7) 0.0232(9) -0.0047(6) 0.0036(7) -0.0009(6) O4 0.0499(11) 0.0161(7) 0.0274(9) 0.0017(7) 0.0051(9) -0.0039(7) C2 0.0196(10) 0.0168(8) 0.0222(11) -0.0031(7) -0.0017(8) 0.0017(7) C3 0.0199(9) 0.0174(9) 0.0225(11) -0.0002(8) -0.0001(9) 0.0002(7) C4 0.0177(10) 0.0244(10) 0.0196(11) -0.0009(8) -0.0007(8) 0.0008(8) C5 0.0163(9) 0.0240(10) 0.0180(11) -0.0063(8) 0.0004(8) 0.0036(8) C6 0.0203(10) 0.0213(9) 0.0260(12) -0.0019(8) -0.0011(9) 0.0005(8) C7 0.0184(10) 0.0197(9) 0.0222(11) 0.0000(8) 0.0020(9) 0.0000(8) C8 0.0172(9) 0.0272(10) 0.0233(11) -0.0022(9) -0.0006(8) -0.0002(8) C9 0.0237(10) 0.0197(9) 0.0220(11) -0.0028(8) 0.0000(9) 0.0005(8) C10 0.0194(9) 0.0156(9) 0.0191(10) -0.0021(7) 0.0000(9) -0.0008(7) C11 0.0151(9) 0.0151(8) 0.0204(10) -0.0029(7) -0.0028(8) -0.0006(7) C12 0.0157(8) 0.0159(8) 0.0221(11) 0.0015(8) 0.0007(9) -0.0006(6) C13 0.0175(9) 0.0185(9) 0.0137(10) -0.0005(7) 0.0004(8) 0.0006(7) C14 0.0147(8) 0.0171(8) 0.0168(10) -0.0001(8) -0.0024(9) 0.0004(6) C15 0.0185(10) 0.0157(8) 0.0187(10) 0.0030(7) 0.0012(8) 0.0002(8) C16 0.0170(9) 0.0223(9) 0.0154(10) -0.0031(8) 0.0021(8) 0.0015(7) C17 0.0326(13) 0.0196(10) 0.0245(12) -0.0078(8) -0.0004(10) -0.0003(9) C20 0.0215(11) 0.0179(9) 0.0203(11) -0.0016(7) -0.0010(9) 0.0007(8) C21 0.0167(8) 0.0184(8) 0.0242(12) -0.0029(8) -0.0033(8) 0.0005(7) C22 0.0201(9) 0.0212(9) 0.0173(11) -0.0014(8) 0.0006(8) 0.0016(8) C23 0.0191(10) 0.0188(9) 0.0201(11) 0.0023(8) 0.0000(8) 0.0006(7) C24 0.0176(9) 0.0138(8) 0.0207(11) -0.0027(7) -0.0022(9) 0.0009(7) C25 0.0217(10) 0.0151(9) 0.0188(11) -0.0028(7) 0.0011(8) 0.0003(7) C26 0.0198(10) 0.0178(9) 0.0221(11) 0.0019(8) 0.0020(9) -0.0015(8) C27 0.0412(13) 0.0186(9) 0.0265(14) -0.0098(9) 0.0010(11) -0.0016(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 C2 1.726(2) . ? S1 C5 1.731(2) . ? O1 C10 1.337(3) . ? O1 C17 1.455(3) . ? O2 C10 1.202(3) . ? O3 C20 1.334(3) . ? O3 C27 1.459(3) . ? O4 C20 1.208(3) . ? C2 C3 1.382(3) . ? C2 C6 1.419(3) . ? C3 C4 1.402(3) . ? C3 H3 0.96(3) . ? C4 C5 1.377(3) . ? C4 H4 0.95(3) . ? C5 C8 1.416(3) . ? C6 C7 1.208(3) . ? C7 C11 1.427(3) . ? C8 C9 1.205(3) . ? C9 C21 1.425(3) . ? C10 C14 1.494(3) . ? C11 C16 1.401(3) . ? C11 C12 1.403(3) . ? C12 C13 1.387(3) . ? C12 H12 0.94(3) . ? C13 C14 1.394(3) . ? C13 H13 0.96(3) . ? C14 C15 1.393(3) . ? C15 C16 1.377(3) . ? C15 H15 0.91(3) . ? C16 H6 0.95(2) . ? C17 H171 0.99(3) . ? C17 H172 0.97(3) . ? C17 H173 0.96(3) . ? C20 C24 1.493(3) . ? C21 C26 1.398(3) . ? C21 C22 1.414(3) . ? C22 C23 1.382(3) . ? C22 H22 0.93(3) . ? C23 C24 1.390(3) . ? C23 H23 1.05(3) . ? C24 C25 1.395(3) . ? C25 C26 1.395(3) . ? C25 H25 0.93(3) . ? C26 H26 0.91(3) . ? C27 H271 0.99(3) . ? C27 H272 0.97(3) . ? C27 H273 0.96(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C5 91.29(11) . . ? C10 O1 C17 114.76(18) . . ? C20 O3 C27 114.68(19) . . ? C3 C2 C6 124.8(2) . . ? C3 C2 S1 111.69(16) . . ? C6 C2 S1 123.46(18) . . ? C2 C3 C4 112.5(2) . . ? C2 C3 H3 124.7(16) . . ? C4 C3 H3 122.8(16) . . ? C5 C4 C3 113.1(2) . . ? C5 C4 H4 118.1(16) . . ? C3 C4 H4 128.8(16) . . ? C4 C5 C8 126.7(2) . . ? C4 C5 S1 111.40(16) . . ? C8 C5 S1 121.91(18) . . ? C7 C6 C2 172.8(2) . . ? C6 C7 C11 173.6(2) . . ? C9 C8 C5 175.0(3) . . ? C8 C9 C21 177.2(3) . . ? O2 C10 O1 123.8(2) . . ? O2 C10 C14 123.6(2) . . ? O1 C10 C14 112.61(17) . . ? C16 C11 C12 119.18(18) . . ? C16 C11 C7 118.4(2) . . ? C12 C11 C7 122.38(19) . . ? C13 C12 C11 120.18(19) . . ? C13 C12 H12 121.7(16) . . ? C11 C12 H12 118.1(16) . . ? C12 C13 C14 119.9(2) . . ? C12 C13 H13 119.7(14) . . ? C14 C13 H13 120.3(14) . . ? C15 C14 C13 120.15(18) . . ? C15 C14 C10 117.59(17) . . ? C13 C14 C10 122.2(2) . . ? C16 C15 C14 120.05(19) . . ? C16 C15 H15 121.3(18) . . ? C14 C15 H15 118.6(18) . . ? C15 C16 C11 120.6(2) . . ? C15 C16 H6 119.5(13) . . ? C11 C16 H6 119.9(13) . . ? O1 C17 H171 109.5(18) . . ? O1 C17 H172 111(2) . . ? H171 C17 H172 112(3) . . ? O1 C17 H173 111.6(17) . . ? H171 C17 H173 96(2) . . ? H172 C17 H173 115(2) . . ? O4 C20 O3 124.2(2) . . ? O4 C20 C24 123.6(2) . . ? O3 C20 C24 112.17(19) . . ? C26 C21 C22 119.30(19) . . ? C26 C21 C9 119.5(2) . . ? C22 C21 C9 121.1(2) . . ? C23 C22 C21 119.9(2) . . ? C23 C22 H22 122.2(15) . . ? C21 C22 H22 117.9(15) . . ? C22 C23 C24 120.6(2) . . ? C22 C23 H23 121.0(17) . . ? C24 C23 H23 118.3(17) . . ? C23 C24 C25 120.00(19) . . ? C23 C24 C20 118.17(19) . . ? C25 C24 C20 121.8(2) . . ? C24 C25 C26 120.0(2) . . ? C24 C25 H25 118.9(17) . . ? C26 C25 H25 121.1(17) . . ? C25 C26 C21 120.2(2) . . ? C25 C26 H26 118.0(17) . . ? C21 C26 H26 121.8(17) . . ? O3 C27 H271 108.3(16) . . ? O3 C27 H272 108.9(17) . . ? H271 C27 H272 115(2) . . ? O3 C27 H273 107(2) . . ? H271 C27 H273 112(3) . . ? H272 C27 H273 105(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.503 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.066 #============================================END data_(2) _database_code_depnum_ccdc_archive 'CCDC 641169' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,5-bis(pentafluorophenylethynyl)thiophene ; _chemical_name_common ? _chemical_melting_point 428(1) _chemical_formula_moiety 'C20 H2 F10 S' _chemical_formula_sum 'C20 H2 F10 S' _chemical_formula_weight 464.28 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/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 4.9212(7) _cell_length_b 31.274(4) _cell_length_c 11.3413(15) _cell_angle_alpha 90.00 _cell_angle_beta 101.83(1) _cell_angle_gamma 90.00 _cell_volume 1708.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7369 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.805 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 4 runs of narrow-frame \w-scans (scan width 0.3\% \w, 26s exposure), every run at a different \f angle. Crystal to detector distance 4.96 cm. ; _diffrn_ambient_temperature 120(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 'Siemens SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_number 0 _diffrn_reflns_number 16756 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3921 _reflns_number_gt 3129 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.049 (Bruker, 1998)' _computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)' _computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXTL version 6.14 (Bruker, 2003)' _computing_structure_refinement 'SHELXTL version 6.14 (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL version 6.14 (Bruker, 2003)' _computing_publication_material 'SHELXTL version 6.14 (Bruker, 2003)' _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. ; _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^)+(0.0423P)^2^+1.3509P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3921 _refine_ls_number_parameters 288 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1100 _refine_ls_wR_factor_gt 0.1028 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 0.14702(12) 0.664049(17) 0.35560(5) 0.02278(14) Uani 1 1 d . . . C2 C 0.0143(4) 0.67351(7) 0.4825(2) 0.0210(4) Uani 1 1 d . . . C3 C 0.1134(5) 0.64478(8) 0.5722(2) 0.0286(5) Uani 1 1 d . . . H3 H 0.065(6) 0.6458(9) 0.648(3) 0.033(7) Uiso 1 1 d . . . C4 C 0.2975(5) 0.61515(8) 0.5389(2) 0.0283(5) Uani 1 1 d . . . H4 H 0.390(5) 0.5947(9) 0.587(2) 0.029(7) Uiso 1 1 d . . . C5 C 0.3377(5) 0.62125(7) 0.4234(2) 0.0222(5) Uani 1 1 d . . . C6 C -0.1743(4) 0.70749(7) 0.48535(19) 0.0220(5) Uani 1 1 d . . . C7 C -0.3352(4) 0.73587(7) 0.48778(19) 0.0214(4) Uani 1 1 d . . . C8 C 0.5097(5) 0.59644(7) 0.3636(2) 0.0243(5) Uani 1 1 d . . . C9 C 0.6558(5) 0.57482(7) 0.3165(2) 0.0245(5) Uani 1 1 d . . . C11 C -0.5311(4) 0.76922(7) 0.48911(19) 0.0199(4) Uani 1 1 d . . . C12 C -0.6096(5) 0.79688(8) 0.3919(2) 0.0253(5) Uani 1 1 d . . . C13 C -0.8022(5) 0.82863(8) 0.3918(2) 0.0308(5) Uani 1 1 d . . . C14 C -0.9245(5) 0.83344(8) 0.4894(2) 0.0300(5) Uani 1 1 d . . . C15 C -0.8512(5) 0.80710(8) 0.5875(2) 0.0281(5) Uani 1 1 d . . . C16 C -0.6568(5) 0.77551(7) 0.5870(2) 0.0234(5) Uani 1 1 d . . . C21 C 0.8312(4) 0.54657(7) 0.2671(2) 0.0231(5) Uani 1 1 d . . . C22 C 0.9571(5) 0.55818(7) 0.1730(2) 0.0244(5) Uani 1 1 d . . . C23 C 1.1318(5) 0.53097(8) 0.1281(2) 0.0267(5) Uani 1 1 d . . . C24 C 1.1825(5) 0.49065(8) 0.1769(2) 0.0310(5) Uani 1 1 d . . . C25 C 1.0597(5) 0.47790(7) 0.2696(2) 0.0327(6) Uani 1 1 d . . . C26 C 0.8855(5) 0.50545(7) 0.3135(2) 0.0273(5) Uani 1 1 d . . . F12 F -0.4908(3) 0.79270(5) 0.29635(13) 0.0398(4) Uani 1 1 d . . . F13 F -0.8683(4) 0.85502(6) 0.29682(16) 0.0516(5) Uani 1 1 d . . . F14 F -1.1149(3) 0.86397(5) 0.48883(17) 0.0487(5) Uani 1 1 d . . . F15 F -0.9729(3) 0.81161(5) 0.68190(14) 0.0439(4) Uani 1 1 d . . . F16 F -0.5897(3) 0.75008(5) 0.68308(12) 0.0340(3) Uani 1 1 d . . . F22 F 0.9143(3) 0.59704(4) 0.12437(13) 0.0341(3) Uani 1 1 d . . . F23 F 1.2543(3) 0.54328(5) 0.03919(13) 0.0379(4) Uani 1 1 d . . . F24 F 1.3507(3) 0.46382(5) 0.13359(16) 0.0449(4) Uani 1 1 d . . . F25 F 1.1072(4) 0.43864(5) 0.31613(17) 0.0515(5) Uani 1 1 d . . . F26 F 0.7632(3) 0.49209(5) 0.40198(14) 0.0397(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 0.0247(3) 0.0192(3) 0.0262(3) -0.0011(2) 0.0094(2) 0.0013(2) C2 0.0214(11) 0.0156(10) 0.0270(11) -0.0051(8) 0.0076(9) -0.0010(8) C3 0.0346(13) 0.0258(12) 0.0270(12) -0.0028(10) 0.0101(10) 0.0042(10) C4 0.0320(13) 0.0207(11) 0.0316(12) 0.0014(10) 0.0055(10) 0.0062(10) C5 0.0215(11) 0.0147(10) 0.0308(12) -0.0051(9) 0.0063(9) -0.0005(8) C6 0.0229(11) 0.0187(11) 0.0246(11) -0.0037(8) 0.0055(9) -0.0030(9) C7 0.0224(11) 0.0186(10) 0.0239(11) -0.0031(9) 0.0067(9) -0.0025(9) C8 0.0224(11) 0.0192(11) 0.0314(12) -0.0048(9) 0.0060(9) -0.0034(9) C9 0.0222(11) 0.0206(11) 0.0301(11) -0.0028(9) 0.0040(9) -0.0015(9) C11 0.0194(10) 0.0150(10) 0.0255(11) -0.0043(8) 0.0049(8) -0.0010(8) C12 0.0259(12) 0.0265(12) 0.0246(11) -0.0010(9) 0.0079(9) -0.0011(9) C13 0.0336(13) 0.0212(12) 0.0346(13) 0.0038(10) -0.0004(10) 0.0029(10) C14 0.0212(11) 0.0197(11) 0.0469(15) -0.0099(10) 0.0018(10) 0.0040(9) C15 0.0219(11) 0.0304(13) 0.0342(13) -0.0141(10) 0.0109(10) -0.0046(9) C16 0.0248(11) 0.0209(11) 0.0249(11) -0.0025(9) 0.0065(9) -0.0033(9) C21 0.0189(11) 0.0189(10) 0.0303(12) -0.0062(9) 0.0021(9) 0.0000(8) C22 0.0250(11) 0.0179(10) 0.0289(12) -0.0053(9) 0.0022(9) -0.0012(9) C23 0.0252(12) 0.0266(12) 0.0288(11) -0.0096(10) 0.0069(9) -0.0032(9) C24 0.0240(12) 0.0256(12) 0.0439(14) -0.0136(11) 0.0084(10) 0.0041(9) C25 0.0330(13) 0.0176(11) 0.0467(15) -0.0002(10) 0.0067(11) 0.0069(10) C26 0.0270(12) 0.0220(11) 0.0340(13) 0.0000(10) 0.0089(10) 0.0001(9) F12 0.0483(9) 0.0464(9) 0.0284(8) 0.0068(7) 0.0166(7) 0.0072(7) F13 0.0565(11) 0.0414(10) 0.0518(10) 0.0197(8) -0.0008(8) 0.0131(8) F14 0.0310(8) 0.0310(8) 0.0812(13) -0.0142(8) 0.0051(8) 0.0122(7) F15 0.0386(9) 0.0531(10) 0.0471(9) -0.0198(8) 0.0252(7) -0.0011(7) F16 0.0436(9) 0.0335(8) 0.0276(7) 0.0048(6) 0.0138(6) -0.0007(6) F22 0.0437(9) 0.0220(7) 0.0381(8) 0.0032(6) 0.0117(7) 0.0041(6) F23 0.0427(9) 0.0383(9) 0.0377(8) -0.0086(7) 0.0201(7) -0.0042(7) F24 0.0378(9) 0.0345(8) 0.0668(11) -0.0164(8) 0.0215(8) 0.0098(7) F25 0.0581(11) 0.0231(8) 0.0779(12) 0.0128(8) 0.0248(9) 0.0157(7) F26 0.0468(9) 0.0285(8) 0.0495(9) 0.0071(7) 0.0229(7) 0.0029(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 C5 1.723(2) . ? S1 C2 1.723(2) . ? C2 C3 1.370(3) . ? C2 C6 1.416(3) . ? C3 C4 1.401(3) . ? C3 H3 0.94(3) . ? C4 C5 1.377(3) . ? C4 H4 0.90(3) . ? C5 C8 1.419(3) . ? C6 C7 1.193(3) . ? C7 C11 1.422(3) . ? C8 C9 1.190(3) . ? C9 C21 1.427(3) . ? C11 C16 1.391(3) . ? C11 C12 1.393(3) . ? C12 F12 1.339(3) . ? C12 C13 1.373(3) . ? C13 F13 1.343(3) . ? C13 C14 1.372(4) . ? C14 F14 1.337(3) . ? C14 C15 1.372(4) . ? C15 F15 1.337(3) . ? C15 C16 1.376(3) . ? C16 F16 1.335(3) . ? C21 C22 1.387(3) . ? C21 C26 1.394(3) . ? C22 F22 1.333(3) . ? C22 C23 1.380(3) . ? C23 F23 1.333(3) . ? C23 C24 1.379(4) . ? C24 F24 1.341(3) . ? C24 C25 1.375(4) . ? C25 F25 1.338(3) . ? C25 C26 1.378(3) . ? C26 F26 1.339(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 C5 S1 C2 91.47(11) . . ? C3 C2 C6 127.6(2) . . ? C3 C2 S1 111.68(17) . . ? C6 C2 S1 120.71(17) . . ? C2 C3 C4 112.6(2) . . ? C2 C3 H3 122.5(17) . . ? C4 C3 H3 124.8(17) . . ? C5 C4 C3 113.1(2) . . ? C5 C4 H4 121.2(17) . . ? C3 C4 H4 125.7(17) . . ? C4 C5 C8 126.5(2) . . ? C4 C5 S1 111.15(17) . . ? C8 C5 S1 122.33(18) . . ? C7 C6 C2 179.4(2) . . ? C6 C7 C11 178.9(2) . . ? C9 C8 C5 177.9(3) . . ? C8 C9 C21 175.7(3) . . ? C16 C11 C12 116.6(2) . . ? C16 C11 C7 121.7(2) . . ? C12 C11 C7 121.7(2) . . ? F12 C12 C13 119.1(2) . . ? F12 C12 C11 118.9(2) . . ? C13 C12 C11 122.0(2) . . ? F13 C13 C14 120.3(2) . . ? F13 C13 C12 119.9(2) . . ? C14 C13 C12 119.7(2) . . ? F14 C14 C13 119.8(2) . . ? F14 C14 C15 120.0(2) . . ? C13 C14 C15 120.2(2) . . ? F15 C15 C14 120.0(2) . . ? F15 C15 C16 120.4(2) . . ? C14 C15 C16 119.6(2) . . ? F16 C16 C15 118.7(2) . . ? F16 C16 C11 119.4(2) . . ? C15 C16 C11 121.9(2) . . ? C22 C21 C26 116.8(2) . . ? C22 C21 C9 122.8(2) . . ? C26 C21 C9 120.5(2) . . ? F22 C22 C23 117.8(2) . . ? F22 C22 C21 120.0(2) . . ? C23 C22 C21 122.2(2) . . ? F23 C23 C24 119.7(2) . . ? F23 C23 C22 120.9(2) . . ? C24 C23 C22 119.4(2) . . ? F24 C24 C25 120.0(2) . . ? F24 C24 C23 120.0(2) . . ? C25 C24 C23 120.0(2) . . ? F25 C25 C24 119.9(2) . . ? F25 C25 C26 120.2(2) . . ? C24 C25 C26 119.9(2) . . ? F26 C26 C25 119.0(2) . . ? F26 C26 C21 119.3(2) . . ? C25 C26 C21 121.7(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.340 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.059 #====================================END