# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2007 data_global _journal_name_full J.Mater.Chem. #=============================================================================== _journal_coden_Cambridge 1145 _publ_section_title ; Molecular Ordering in Bis(phenylenyl)bithiophenes ; _publ_contact_author_name 'Yves Chabal' _publ_contact_author_address ; Biomedical Engineering 599 Taylor Road Rutgers University Piscataway, NJ 08854, USA ; _publ_contact_author_email yves@rutchem.rutgers.edu _publ_contact_author_phone '(732) 445-8248' _publ_contact_author_fax '(732) 445-4991' loop_ _publ_author_name _publ_author_address M.Stokes ; Biomedical Engineering 599 Taylor Road Rutgers University Piscataway, NJ 08854, USA ; R.Kortan ; Physics Department Koc University Istanbul, Turkey ; S.A.Rivillon ; Chemistry and Chemical Biology Rutgers University Piscataway, NJ 08854, USA ; H.E.Katz ; Material Science and Engineering Johns Hopkins University Baltimore, MD 21218, USA ; Y.Chabal ; Biomedical Engineering 599 Taylor Road Rutgers University Piscataway, NJ 08854, USA ; C.Kloc ; Bell Laboratories Alcatel-Lucent Murray Hill, NJ 07974, USA ; ; T.Siegrist ; ; Bell Laboratories Alcatel-Lucent Murray Hill, NJ 07974, USA ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_volume ? _journal_year ? # Attachment '2pttp2_300K.cif' data_2pttp2_300K _database_code_depnum_ccdc_archive 'CCDC 297725' _oxford_structure_analysis_title '2pttp2 at 300K P2(1)/a' _chemical_name_systematic 5,5'-bis(4-ethylphenyl)-2,2'-bithiophene _chemical_melting_point ? _cell_length_a 9.242(4) _cell_length_b 5.7180(11) _cell_length_c 18.205(6) _cell_angle_alpha 90 _cell_angle_beta 100.06(3) _cell_angle_gamma 90 _cell_volume 947.3(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/a ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z x+1/2,-y+1/2,z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C48 H40 S4 # Dc = 2.61 Fooo = 396.00 Mu = 5.71 M = 372.55 # Found Formula = C24 H22 S2 # Dc = 1.31 FOOO = 396.00 Mu = 2.86 M = 187.29 _chemical_formula_sum 'C24 H22 S2' _chemical_formula_moiety 'C24 H22 S2' _chemical_compound_source ? _chemical_formula_weight 374.57 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 300 _exptl_crystal_description platelet _exptl_crystal_colour yellow _exptl_crystal_size_min 0.015 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_max 0.22 _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.286 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.97 _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 300 _diffrn_reflns_number 8895 _reflns_number_total 2978 _diffrn_reflns_av_R_equivalents 0.078 # Number of reflections with Friedels Law is 2978 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3450 _diffrn_reflns_theta_min 3.410 _diffrn_reflns_theta_max 32.575 _diffrn_measured_fraction_theta_max 0.863 _diffrn_reflns_theta_full 25.083 _diffrn_measured_fraction_theta_full 0.949 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -13 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 27 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.73 _refine_diff_density_max 0.72 _refine_ls_number_reflns 1194 _refine_ls_number_restraints 0 _refine_ls_number_parameters 118 #_refine_ls_R_factor_ref 0.1888 _refine_ls_wR_factor_ref 0.1943 _refine_ls_goodness_of_fit_ref 0.9467 #_reflns_number_all 1194 _refine_ls_R_factor_all 0.1888 _refine_ls_wR_factor_all 0.1943 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 258 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_gt 0.0826 _refine_ls_shift/su_max 0.000226 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed # WARNING. The IUCr will not accept Unit Weights _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Quasi-Unit weights W = 1.0 or 1./2F ; # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. North, A.C.T., Phillips, D.C. & Mathews, F.S., (1968). Acta Cryst, A24, 351-359. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2002). Xcalibur User Manual. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.5210(10) 0.9665(16) 0.4663(5) 0.0588 1.0000 Uani . . . . . . S2 S 0.6330(3) 1.1390(4) 0.42380(15) 0.0735 1.0000 Uani . . . . . . C3 C 0.6299(11) 0.9473(16) 0.3514(5) 0.0639 1.0000 Uani . . . . . . C4 C 0.7072(10) 0.9957(16) 0.2897(6) 0.0610 1.0000 Uani . . . . . . C5 C 0.7869(11) 1.1944(18) 0.2872(6) 0.0678 1.0000 Uani . . . . . . C6 C 0.8606(12) 1.2407(19) 0.2303(6) 0.0784 1.0000 Uani . . . . . . C7 C 0.8632(11) 1.085(2) 0.1743(6) 0.0790 1.0000 Uani . . . . . . C8 C 0.7802(13) 0.882(2) 0.1758(6) 0.0903 1.0000 Uani . . . . . . C9 C 0.7053(12) 0.8423(18) 0.2322(6) 0.0788 1.0000 Uani . . . . . . C10 C 0.9471(14) 1.117(2) 0.1123(7) 0.1031 1.0000 Uani . . . . . . C11 C 0.8820(18) 1.271(3) 0.0575(8) 0.1582 1.0000 Uani . . . . . . C12 C 0.5462(12) 0.7634(17) 0.3608(6) 0.0725 1.0000 Uani . . . . . . C13 C 0.4865(11) 0.7750(17) 0.4256(6) 0.0702 1.0000 Uani . . . . . . H51 H 0.7903 1.3050 0.3258 0.0820 1.0000 Uiso R . . . . . H61 H 0.9154 1.3858 0.2306 0.1000 1.0000 Uiso R . . . . . H81 H 0.7749 0.7705 0.1363 0.1220 1.0000 Uiso R . . . . . H91 H 0.6492 0.7016 0.2316 0.1000 1.0000 Uiso R . . . . . H111 H 0.9354 1.2811 0.0175 0.2560 1.0000 Uiso R . . . . . H112 H 0.8786 1.4249 0.0800 0.2560 1.0000 Uiso R . . . . . H113 H 0.7836 1.2197 0.0398 0.2560 1.0000 Uiso R . . . . . H121 H 0.5253 0.6412 0.3261 0.1010 1.0000 Uiso R . . . . . H131 H 0.4288 0.6467 0.4391 0.0900 1.0000 Uiso R . . . . . H101 H 1.0502 1.1766 0.1358 0.1276 1.0000 Uiso R . . . . . H102 H 0.9623 0.9582 0.0904 0.1276 1.0000 Uiso 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 C1 0.073(7) 0.038(6) 0.065(6) 0.010(6) 0.013(5) -0.006(5) S2 0.0933(19) 0.0437(14) 0.0856(18) -0.0061(16) 0.0217(14) -0.0147(17) C3 0.074(7) 0.046(6) 0.066(6) 0.001(5) -0.001(6) -0.010(6) C4 0.062(6) 0.032(5) 0.088(8) 0.001(6) 0.010(6) 0.003(5) C5 0.073(7) 0.069(8) 0.061(7) -0.010(6) 0.009(6) 0.008(6) C6 0.090(8) 0.071(7) 0.076(7) -0.008(7) 0.019(7) -0.006(6) C7 0.079(8) 0.080(9) 0.083(8) 0.022(7) 0.029(7) -0.012(7) C8 0.110(9) 0.081(9) 0.085(8) -0.007(7) 0.031(7) 0.006(9) C9 0.115(9) 0.042(6) 0.083(7) -0.005(6) 0.026(7) 0.005(7) C10 0.129(10) 0.074(8) 0.108(10) 0.008(8) 0.025(9) -0.002(8) C11 0.237(18) 0.126(13) 0.133(13) 0.024(11) 0.091(13) 0.022(13) C12 0.089(8) 0.047(6) 0.082(8) -0.010(6) 0.015(6) -0.013(6) C13 0.074(7) 0.050(7) 0.091(8) 0.005(6) 0.026(6) -0.018(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.687(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C1 2_676 1.403(18) yes C1 . S2 . 1.710(9) yes C1 . C13 . 1.329(12) yes S2 . C3 . 1.710(10) yes C3 . C4 . 1.459(13) yes C3 . C12 . 1.334(12) yes C4 . C5 . 1.359(12) yes C4 . C9 . 1.363(12) yes C5 . C6 . 1.363(13) yes C5 . H51 . 0.941 no C6 . C7 . 1.355(13) yes C6 . H61 . 0.971 no C7 . C8 . 1.395(14) yes C7 . C10 . 1.488(15) yes C8 . C9 . 1.355(13) yes C8 . H81 . 0.956 no C9 . H91 . 0.956 no C10 . C11 . 1.385(14) yes C10 . H101 . 1.031 no C10 . H102 . 1.014 no C11 . H111 . 0.951 no C11 . H112 . 0.973 no C11 . H113 . 0.957 no C12 . C13 . 1.389(13) yes C12 . H121 . 0.939 no C13 . H131 . 0.964 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 2_676 C1 . S2 . 121.3(10) yes C1 2_676 C1 . C13 . 129.5(11) yes S2 . C1 . C13 . 109.2(7) yes C1 . S2 . C3 . 92.8(5) yes S2 . C3 . C4 . 121.8(7) yes S2 . C3 . C12 . 109.8(8) yes C4 . C3 . C12 . 128.4(9) yes C3 . C4 . C5 . 121.7(9) yes C3 . C4 . C9 . 121.8(9) yes C5 . C4 . C9 . 116.5(10) yes C4 . C5 . C6 . 122.3(9) yes C4 . C5 . H51 . 119.0 no C6 . C5 . H51 . 118.7 no C5 . C6 . C7 . 121.4(10) yes C5 . C6 . H61 . 119.3 no C7 . C6 . H61 . 119.2 no C6 . C7 . C8 . 116.7(10) yes C6 . C7 . C10 . 124.6(11) yes C8 . C7 . C10 . 118.6(11) yes C7 . C8 . C9 . 120.7(11) yes C7 . C8 . H81 . 119.8 no C9 . C8 . H81 . 119.5 no C4 . C9 . C8 . 122.3(11) yes C4 . C9 . H91 . 118.9 no C8 . C9 . H91 . 118.7 no C7 . C10 . C11 . 114.0(12) yes C7 . C10 . H101 . 107.1 no C11 . C10 . H101 . 110.1 no C7 . C10 . H102 . 108.3 no C11 . C10 . H102 . 111.0 no H101 . C10 . H102 . 106.0 no C10 . C11 . H111 . 111.9 no C10 . C11 . H112 . 108.2 no H111 . C11 . H112 . 109.1 no C10 . C11 . H113 . 108.4 no H111 . C11 . H113 . 110.4 no H112 . C11 . H113 . 108.7 no C3 . C12 . C13 . 113.3(9) yes C3 . C12 . H121 . 123.8 no C13 . C12 . H121 . 122.8 no C12 . C13 . C1 . 114.9(9) yes C12 . C13 . H131 . 120.0 no C1 . C13 . H131 . 125.0 no _chemical_name_common 5,5'-bis(4-ethylphenyl)-2,2'-bithiophene # Attachment 'HOPTTPOH.cif' #======================================================================== data_HOPTTPOH _database_code_depnum_ccdc_archive 'CCDC 299841' #======================================================================== _chemical_name_systematic 5,5'-bis(4-hydroxyphenyl)-2,2'-bithiophene _chemical_formula_sum 'C20 H14 S2 O2' _chemical_formula_moiety 'C20 H14 S2 O2' _diffrn_measurement_device_type 'NSLS Beamline X22A' _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 1.2084 _computing_structure_solution 'FOX http://objcryst.sourceforge.net' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source C C 'International Tables for Crystallography (Vol. IV)' S S 'International Tables for Crystallography (Vol. IV)' O O 'International Tables for Crystallography (Vol. IV)' H H 'International Tables for Crystallography (Vol. IV)' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall ' P 2ac 2ab' _cell_length_a 5.558(3) _cell_length_b 7.665(4) _cell_length_c 37.188(25) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type C C1 0.5354 0.5180 -0.0041 0.0127 1.0000 Uiso C C2 0.3309 0.5924 -0.0150 0.0127 1.0000 Uiso C C3 0.3047 0.5910 -0.0543 0.0127 1.0000 Uiso C C4 0.4902 0.5158 -0.0712 0.0127 1.0000 Uiso S S5 0.7140 0.4398 -0.0404 0.0127 1.0000 Uiso C C6 0.5180 0.4939 -0.1105 0.0127 1.0000 Uiso C C7 0.7135 0.4159 -0.1240 0.0127 1.0000 Uiso C C8 0.7468 0.3920 -0.1629 0.0127 1.0000 Uiso C C9 0.5790 0.4490 -0.1858 0.0127 1.0000 Uiso C C10 0.3632 0.5349 -0.1715 0.0127 1.0000 Uiso C C11 0.3345 0.5560 -0.1361 0.0127 1.0000 Uiso O O12 0.6043 0.4291 -0.2213 0.0127 1.0000 Uiso C C13 0.6112 0.5002 0.0336 0.0127 1.0000 Uiso S S14 0.4327 0.5784 0.0699 0.0127 1.0000 Uiso C C15 0.6564 0.5025 0.1007 0.0127 1.0000 Uiso C C16 0.8419 0.4272 0.0839 0.0127 1.0000 Uiso C C17 0.8157 0.4258 0.0445 0.0127 1.0000 Uiso C C18 0.6284 0.5244 0.1400 0.0127 1.0000 Uiso C C19 0.8119 0.4623 0.1657 0.0127 1.0000 Uiso C C20 0.7842 0.4830 0.2012 0.0127 1.0000 Uiso C C21 0.5674 0.5693 0.2153 0.0127 1.0000 Uiso C C22 0.4003 0.6260 0.1924 0.0127 1.0000 Uiso C C23 0.4327 0.6025 0.1534 0.0127 1.0000 Uiso O O24 0.5364 0.5913 0.2506 0.0127 1.0000 Uiso H H25 0.1972 0.6483 0.0030 0.0127 1.0000 Uiso H H26 0.1471 0.6470 -0.0672 0.0127 1.0000 Uiso H H27 0.8553 0.3672 -0.1064 0.0127 1.0000 Uiso H H28 0.9105 0.3273 -0.1720 0.0127 1.0000 Uiso H H29 0.2259 0.5816 -0.1901 0.0127 1.0000 Uiso H H30 0.1712 0.6206 -0.1271 0.0127 1.0000 Uiso H H31 0.7497 0.3721 -0.2278 0.0127 1.0000 Uiso H H32 0.9996 0.3712 0.0967 0.0127 1.0000 Uiso H H33 0.9494 0.3699 0.0265 0.0127 1.0000 Uiso H H34 0.9750 0.3978 0.1566 0.0127 1.0000 Uiso H H35 0.9242 0.4351 0.2192 0.0127 1.0000 Uiso H H36 0.2391 0.6901 0.2025 0.0127 1.0000 Uiso H H37 0.2907 0.6513 0.1360 0.0127 1.0000 Uiso H H38 0.6671 0.5456 0.2641 0.0127 1.0000 Uiso _publ_section_exptl_refinement ; The powder data were analyzed by CMPR[1] and Crysfire[2] sub-algorithms to determine the unit cell. Chekcell[3] then examined Crysfire solutions, and the space groups were identified. PowderCell[4] was used for manual trials of calculating the diffraction pattern for different cell decorations and space groups. We have used the ab-initio reverse Monte-Carlo structure determination program Fox[5] to identify the molecular conformations and cell decorations by real-space simulations. The initial minimum energy molecular shapes of fully planar molecules and other structural parameters of molecules were determined by Ghemical[6]. 1. Brian Toby, The portable CMPR&Logic programs, http://www.ncnr.nist.gov/programs/crystallography/software/cmpr/ . 2. R. Shirley, Measurement and Analysis of Powder Data from Single Solid Phases, in Methods and applications in crystallographic computing, Hall, S. R. & Ashida, T., Clarendon Press, Oxford, 1984, 411-437. 3. Jean Laugier and Bernard Bochu , LMGP suite for Windows, Laboratoire des Materiaux et du G\'enie Physique de l'Ecole Sup\'erieure de Physique de Grenoble, http://www.inpg.fr/LMGP . 4. G. Reck, W. Kraus, G. Nolze, GECM-15, Dresden, Germany. Munich: R. Oldenburg, Verlag, 1994 5. V. Favre-Nicolin, R. Cerny, J. Appl. Crystallogr. 2002, 35, 734. 6. J. Jensen, D. Curtis, ghemical-GMS, http://www.uiowa.edu/\~ghemical/ ; _chemical_name_common 5,5'-bis(4-hydroxyphenyl)-2,2'-bithiophene # Attachment 'HO6PTTP6OH.cif' data_HO6PTTP6OH _database_code_depnum_ccdc_archive 'CCDC 299842' _chemical_name_systematic 5,5'-bis-4-(6-hydroxyhexyloxy)-phenyl-2,2'-bithiophene _chemical_formula_sum 'C32 H38 S2 O4' _chemical_formula_moiety 'C32 H38 S2 O4' _diffrn_measurement_device_type 'NSLS Beamline X22A' _diffrn_radiation_monochromator silicon _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 1.2084 _computing_structure_solution 'FOX http://objcryst.sourceforge.net' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source H H 'International Tables for Crystallography (Vol. IV)' O O 'International Tables for Crystallography (Vol. IV)' C C 'International Tables for Crystallography (Vol. IV)' S S 'International Tables for Crystallography (Vol. IV)' _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall ' P 2yb' _cell_length_a 33.056(22) _cell_length_b 7.485(4) _cell_length_c 5.876(3) _cell_angle_alpha 90.000 _cell_angle_beta 96.16(3) _cell_angle_gamma 90.000 loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type H H1 0.9398 0.7184 1.4246 0.0127 1.0000 Uiso O O2 0.9118 0.6893 1.4174 0.0127 1.0000 Uiso C C3 0.8912 0.7408 1.2009 0.0127 1.0000 Uiso H H4 0.9072 0.6804 1.0684 0.0127 1.0000 Uiso H H5 0.8976 0.8811 1.1749 0.0127 1.0000 Uiso C C6 0.8454 0.6975 1.1769 0.0127 1.0000 Uiso H H7 0.8421 0.5565 1.2150 0.0127 1.0000 Uiso H H8 0.8326 0.7573 1.3216 0.0127 1.0000 Uiso C C9 0.8232 0.7529 0.9438 0.0127 1.0000 Uiso H H10 0.8392 0.6925 0.8112 0.0127 1.0000 Uiso H H11 0.8296 0.8932 0.9178 0.0127 1.0000 Uiso C C12 0.7774 0.7095 0.9198 0.0127 1.0000 Uiso H H13 0.7741 0.5686 0.9578 0.0127 1.0000 Uiso H H14 0.7646 0.7693 1.0644 0.0127 1.0000 Uiso C C15 0.7552 0.7649 0.6866 0.0127 1.0000 Uiso H H16 0.7712 0.7046 0.5540 0.0127 1.0000 Uiso H H17 0.7616 0.9053 0.6606 0.0127 1.0000 Uiso C C18 0.7094 0.7216 0.6626 0.0127 1.0000 Uiso H H19 0.7061 0.5807 0.7007 0.0127 1.0000 Uiso H H20 0.6966 0.7814 0.8072 0.0127 1.0000 Uiso O O21 0.6912 0.7749 0.4488 0.0127 1.0000 Uiso C C22 0.6479 0.7536 0.4182 0.0127 1.0000 Uiso C C23 0.6288 0.6436 0.5662 0.0127 1.0000 Uiso C C24 0.5866 0.6228 0.5363 0.0127 1.0000 Uiso C C25 0.5635 0.7120 0.3584 0.0127 1.0000 Uiso C C26 0.5826 0.8221 0.2104 0.0127 1.0000 Uiso C C27 0.6248 0.8429 0.2403 0.0127 1.0000 Uiso H H28 0.6397 0.9285 0.1251 0.0127 1.0000 Uiso H H29 0.5646 0.8915 0.0720 0.0127 1.0000 Uiso H H30 0.5717 0.5372 0.6515 0.0127 1.0000 Uiso H H31 0.6468 0.5741 0.7046 0.0127 1.0000 Uiso C C32 0.5169 0.6891 0.3254 0.0127 1.0000 Uiso C C33 0.4904 0.5780 0.4642 0.0127 1.0000 Uiso C C34 0.4476 0.5969 0.3697 0.0127 1.0000 Uiso C C35 0.4451 0.7181 0.1714 0.0127 1.0000 Uiso S S36 0.4880 0.7947 0.1126 0.0127 1.0000 Uiso H H37 0.5031 0.4989 0.6101 0.0127 1.0000 Uiso H H38 0.4210 0.5345 0.4299 0.0127 1.0000 Uiso C C39 0.4047 0.7678 0.0310 0.0127 1.0000 Uiso C C40 0.3977 0.8893 -0.1745 0.0127 1.0000 Uiso C C41 0.3573 0.8965 -0.2466 0.0127 1.0000 Uiso C C42 0.3351 0.7829 -0.0973 0.0127 1.0000 Uiso S S43 0.3632 0.6838 0.1037 0.0127 1.0000 Uiso H H44 0.4227 0.9568 -0.2455 0.0127 1.0000 Uiso H H45 0.3422 0.9718 -0.3900 0.0127 1.0000 Uiso C C46 0.2886 0.7600 -0.1302 0.0127 1.0000 Uiso C C47 0.2654 0.8492 -0.3081 0.0127 1.0000 Uiso C C48 0.2232 0.8284 -0.3380 0.0127 1.0000 Uiso C C49 0.2041 0.7183 -0.1900 0.0127 1.0000 Uiso C C50 0.2272 0.6291 -0.0121 0.0127 1.0000 Uiso C C51 0.2695 0.6499 0.0178 0.0127 1.0000 Uiso H H52 0.2803 0.9348 -0.4233 0.0127 1.0000 Uiso H H53 0.2052 0.8978 -0.4764 0.0127 1.0000 Uiso H H54 0.2124 0.5435 0.1031 0.0127 1.0000 Uiso H H55 0.2875 0.5805 0.1562 0.0127 1.0000 Uiso O O56 0.1609 0.6970 -0.2205 0.0127 1.0000 Uiso C C57 0.1488 0.7067 -0.4664 0.0127 1.0000 Uiso C C58 0.1022 0.7056 -0.5197 0.0127 1.0000 Uiso C C59 0.0895 0.7157 -0.7793 0.0127 1.0000 Uiso C C60 0.0428 0.7146 -0.8326 0.0127 1.0000 Uiso C C61 0.0301 0.7248 -1.0922 0.0127 1.0000 Uiso C C62 -0.0165 0.7237 -1.1454 0.0127 1.0000 Uiso O O63 -0.0283 0.7331 -1.3865 0.0127 1.0000 Uiso H H64 0.1628 0.8203 -0.5422 0.0127 1.0000 Uiso H H65 0.1634 0.6022 -0.5570 0.0127 1.0000 Uiso H H66 0.0907 0.5894 -0.4365 0.0127 1.0000 Uiso H H67 0.0902 0.8123 -0.4213 0.0127 1.0000 Uiso H H68 0.1044 0.8314 -0.8446 0.0127 1.0000 Uiso H H69 0.1049 0.6085 -0.8598 0.0127 1.0000 Uiso H H70 0.0314 0.5984 -0.7494 0.0127 1.0000 Uiso H H71 0.0308 0.8213 -0.7342 0.0127 1.0000 Uiso H H72 0.0456 0.6176 -1.1727 0.0127 1.0000 Uiso H H73 0.0450 0.8405 -1.1575 0.0127 1.0000 Uiso H H74 -0.0280 0.6075 -1.0622 0.0127 1.0000 Uiso H H75 -0.0285 0.8304 -1.0471 0.0127 1.0000 Uiso H H76 -0.0050 0.7383 -1.4673 0.0127 1.0000 Uiso _publ_section_exptl_refinement ; The powder data were analyzed by CMPR[1] and Crysfire[2] sub-algorithms to determine the unit cell. Chekcell[3] then examined Crysfire solutions, and the space groups were identified. PowderCell[4] was used for manual trials of calculating the diffraction pattern for different cell decorations and space groups. We have used the ab-initio reverse Monte-Carlo structure determination program Fox[5] to identify the molecular conformations and cell decorations by real-space simulations. The initial minimum energy molecular shapes of fully planar molecules and other structural parameters of molecules were determined by Ghemical[6]. 1. Brian Toby, The portable CMPR&Logic programs, http://www.ncnr.nist.gov/programs/crystallography/software/cmpr/ . 2. R. Shirley, Measurement and Analysis of Powder Data from Single Solid Phases, in Methods and applications in crystallographic computing, Hall, S. R. & Ashida, T., Clarendon Press, Oxford, 1984, 411-437. 3. Jean Laugier and Bernard Bochu , LMGP suite for Windows, Laboratoire des Materiaux et du G\'enie Physique de l'Ecole Sup\'erieure de Physique de Grenoble, http://www.inpg.fr/LMGP . 4. G. Reck, W. Kraus, G. Nolze, GECM-15, Dresden, Germany. Munich: R. Oldenburg, Verlag, 1994 5. V. Favre-Nicolin, R. Cerny, J. Appl. Crystallogr. 2002, 35, 734. 6. J. Jensen, D. Curtis, ghemical-GMS, http://www.uiowa.edu/\~ghemical/ . ; _chemical_name_common 5,5'-bis-4-(6-hydroxyhexyloxy)-phenyl-2,2'-bithiophene data_2pttp2_120 _database_code_depnum_ccdc_archive 'CCDC 634487' #=============================================================================== _oxford_structure_analysis_title '2pttp2 at 120K absorption corr P2(1)/a' _chemical_name_systematic 5,5'-bis(4-ethylphenyl)-2,2'-bithiophene _chemical_melting_point ? _cell_length_a 9.109(2) _cell_length_b 5.7272(7) _cell_length_c 18.159(4) _cell_angle_alpha 90 _cell_angle_beta 101.54(2) _cell_angle_gamma 90 _cell_volume 928.1(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/a ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z x+1/2,-y+1/2,z _cell_formula_units_Z 2 # Given Formula = C24 H22 S2 # Dc = 1.34 Fooo = 396.00 Mu = 2.92 M = 187.29 # Found Formula = C24 H22 S2 # Dc = 1.34 FOOO = 396.00 Mu = 2.92 M = 187.29 _chemical_formula_sum 'C24 H22 S2' _chemical_formula_moiety 'C24 H22 S2' _chemical_compound_source ? _chemical_formula_weight 374.57 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description platelet _exptl_crystal_colour yellow _exptl_crystal_size_min 0.015 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_max 0.22 _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.292 _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_structure_solution 'NRCVAX (Gabe et al., 1989)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 5569 _reflns_number_total 2046 _diffrn_reflns_av_R_equivalents 0.090 # Number of reflections with Friedels Law is 2046 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2194 _diffrn_reflns_theta_min 3.435 _diffrn_reflns_theta_max 27.785 _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 25.285 _diffrn_measured_fraction_theta_full 0.948 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 10 _reflns_limit_h_min -11 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.72 _refine_diff_density_max 0.73 _refine_ls_number_reflns 973 _refine_ls_number_restraints 0 _refine_ls_number_parameters 118 #_refine_ls_R_factor_ref 0.0824 _refine_ls_wR_factor_ref 0.0505 _refine_ls_goodness_of_fit_ref 1.0829 #_reflns_number_all 2044 _refine_ls_R_factor_all 0.1710 _refine_ls_wR_factor_all 0.3420 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.1\s(I) _reflns_number_gt 973 _refine_ls_R_factor_gt 0.0824 _refine_ls_wR_factor_gt 0.0505 _refine_ls_shift/su_max 0.000155 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.01P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _exptl_absorpt_correction_type empirical # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined structure solution reference Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. North, A.C.T., Phillips, D.C. & Mathews, F.S., (1968). Acta Cryst, A24, 351-359. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2002). Xcalibur User Manual. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Gabe, E.J., Le Page, Y., Charland,.J.-P., Lee, F.L. and White, P.S. (1989) J. Appl. Cryst., 22, 384-387. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens S1 S 0.6317(2) -0.1427(3) 0.42250(10) 0.0318 1.0000 Uani . . . . . . C2 C 0.5210(7) 0.0352(11) 0.4668(3) 0.0271 1.0000 Uani . . . . . . C3 C 0.4846(7) 0.2309(11) 0.4253(3) 0.0324 1.0000 Uani . . . . . . C4 C 0.5425(6) 0.2396(10) 0.3587(3) 0.0274 1.0000 Uani . . . . . . C5 C 0.6272(7) 0.0501(11) 0.3489(3) 0.0270 1.0000 Uani . . . . . . C6 C 0.7029(6) 0.0044(11) 0.2882(3) 0.0231 1.0000 Uani . . . . . . C7 C 0.7826(6) -0.2008(10) 0.2834(3) 0.0266 1.0000 Uani . . . . . . C8 C 0.8570(7) -0.2396(11) 0.2257(3) 0.0295 1.0000 Uani . . . . . . C9 C 0.8591(7) -0.0759(12) 0.1700(3) 0.0279 1.0000 Uani . . . . . . C10 C 0.7760(6) 0.1261(12) 0.1732(3) 0.0299 1.0000 Uani . . . . . . C11 C 0.7026(6) 0.1625(12) 0.2307(3) 0.0325 1.0000 Uani . . . . . . C12 C 0.9435(7) -0.1159(12) 0.1092(3) 0.0390 1.0000 Uani . . . . . . C13 C 0.8737(8) -0.2878(11) 0.0517(3) 0.0510 1.0000 Uani . . . . . . H31 H 0.4257 0.3477 0.4404 0.0397 1.0000 Uiso R . . . . . H41 H 0.5233 0.3610 0.3240 0.0328 1.0000 Uiso R . . . . . H71 H 0.7861 -0.3138 0.3206 0.0305 1.0000 Uiso R . . . . . H81 H 0.9092 -0.3773 0.2243 0.0349 1.0000 Uiso R . . . . . H101 H 0.7714 0.2368 0.1353 0.0358 1.0000 Uiso R . . . . . H111 H 0.6487 0.2986 0.2314 0.0390 1.0000 Uiso R . . . . . H121 H 1.0382 -0.1742 0.1329 0.0465 1.0000 Uiso R . . . . . H122 H 0.9553 0.0292 0.0840 0.0472 1.0000 Uiso R . . . . . H131 H 0.9314 -0.2999 0.0119 0.0798 1.0000 Uiso R . . . . . H132 H 0.8752 -0.4362 0.0764 0.0800 1.0000 Uiso R . . . . . H133 H 0.7730 -0.2465 0.0299 0.0798 1.0000 Uiso 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 0.0408(10) 0.0158(9) 0.0408(9) 0.0022(11) 0.0131(8) 0.0051(11) C2 0.031(4) 0.020(4) 0.031(4) -0.009(4) 0.007(3) 0.002(3) C3 0.039(4) 0.020(4) 0.042(4) 0.001(4) 0.018(4) 0.007(4) C4 0.034(4) 0.019(4) 0.028(4) 0.009(3) 0.003(3) 0.004(3) C5 0.035(4) 0.021(4) 0.026(4) -0.001(3) 0.007(3) 0.005(3) C6 0.025(4) 0.009(4) 0.034(4) 0.003(3) 0.003(3) -0.001(3) C7 0.027(4) 0.023(4) 0.027(4) 0.006(3) 0.000(3) -0.001(3) C8 0.031(4) 0.025(4) 0.032(4) -0.004(3) 0.007(3) 0.004(3) C9 0.022(4) 0.033(5) 0.029(4) -0.008(4) 0.005(3) -0.004(3) C10 0.032(4) 0.022(4) 0.037(4) 0.002(4) 0.009(3) -0.004(4) C11 0.040(4) 0.017(4) 0.041(4) 0.001(4) 0.010(3) 0.008(4) C12 0.049(4) 0.030(4) 0.038(4) 0.006(4) 0.012(3) 0.002(4) C13 0.071(5) 0.044(5) 0.044(5) -0.007(4) 0.027(4) -0.004(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.704(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 . C2 . 1.740(6) yes S1 . C5 . 1.727(6) yes C2 . C2 2_656 1.394(11) yes C2 . C3 . 1.354(8) yes C3 . C4 . 1.414(8) yes C3 . H31 . 0.932 no C4 . C5 . 1.364(7) yes C4 . H41 . 0.932 no C5 . C6 . 1.436(7) yes C6 . C7 . 1.394(7) yes C6 . C11 . 1.382(7) yes C7 . C8 . 1.374(8) yes C7 . H71 . 0.932 no C8 . C9 . 1.382(7) yes C8 . H81 . 0.924 no C9 . C10 . 1.390(8) yes C9 . C12 . 1.484(8) yes C10 . C11 . 1.365(7) yes C10 . H101 . 0.930 no C11 . H111 . 0.923 no C12 . C13 . 1.483(7) yes C12 . H121 . 0.945 no C12 . H122 . 0.965 no C13 . H131 . 0.977 no C13 . H132 . 0.960 no C13 . H133 . 0.953 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . S1 . C5 . 93.3(3) yes S1 . C2 . C2 2_656 121.0(7) yes S1 . C2 . C3 . 109.1(4) yes C2 2_656 C2 . C3 . 129.9(8) yes C2 . C3 . C4 . 114.4(6) yes C2 . C3 . H31 . 121.4 no C4 . C3 . H31 . 124.1 no C3 . C4 . C5 . 113.7(6) yes C3 . C4 . H41 . 123.6 no C5 . C4 . H41 . 122.7 no S1 . C5 . C4 . 109.5(4) yes S1 . C5 . C6 . 122.4(5) yes C4 . C5 . C6 . 128.0(6) yes C5 . C6 . C7 . 122.6(6) yes C5 . C6 . C11 . 122.2(6) yes C7 . C6 . C11 . 115.3(5) yes C6 . C7 . C8 . 121.8(6) yes C6 . C7 . H71 . 118.8 no C8 . C7 . H71 . 119.3 no C7 . C8 . C9 . 121.9(6) yes C7 . C8 . H81 . 119.6 no C9 . C8 . H81 . 118.5 no C8 . C9 . C10 . 116.6(5) yes C8 . C9 . C12 . 121.6(6) yes C10 . C9 . C12 . 121.8(6) yes C9 . C10 . C11 . 120.8(6) yes C9 . C10 . H101 . 118.8 no C11 . C10 . H101 . 120.4 no C6 . C11 . C10 . 123.5(6) yes C6 . C11 . H111 . 117.6 no C10 . C11 . H111 . 118.9 no C9 . C12 . C13 . 114.5(6) yes C9 . C12 . H121 . 106.1 no C13 . C12 . H121 . 108.0 no C9 . C12 . H122 . 110.1 no C13 . C12 . H122 . 108.1 no H121 . C12 . H122 . 109.9 no C12 . C13 . H131 . 110.4 no C12 . C13 . H132 . 107.1 no H131 . C13 . H132 . 108.9 no C12 . C13 . H133 . 111.6 no H131 . C13 . H133 . 109.1 no H132 . C13 . H133 . 109.7 no _chemical_name_common 5,5'-bis(4-ethylphenyl)-2,2'-bithiophene