#------------------------------------------------------------------------------ #$Date: 2019-10-08 12:32:51 +0300 (Tue, 08 Oct 2019) $ #$Revision: 219162 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/44/7234472.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7234472 loop_ _publ_author_name 'Junwei Yang' 'Moyun Chen' 'Ji Ma' 'Wei Huang' 'Haoyun Zhu' 'Yuli Huang' 'Weizhi Wang' _publ_section_title ; Boronate ester post-functionalization of PPEs: versatile building blocks for poly(2,2'-(1-(4-(1,2-di(thiophen-2-yl)vinyl)phenyl)-2- (2,5-dioctylphenyl)ethene-1,2-diyl)dithiophene) and application in field effect transistors ; _journal_name_full 'Journal of Materials Chemistry C' _journal_page_first 10074 _journal_page_last 10078 _journal_paper_doi 10.1039/C5TC02298C _journal_volume 3 _journal_year 2015 _chemical_formula_sum 'C22 H14' _chemical_formula_weight 278.33 _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.34 _cell_angle_beta 94.20 _cell_angle_gamma 103.93 _cell_formula_units_Z 2 _cell_length_a 6.055(3) _cell_length_b 9.804(4) _cell_length_c 13.814(2) _cell_measurement_reflns_used 660 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 23.16 _cell_measurement_theta_min 2.96 _cell_volume 793.6(5) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 4003 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.14 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_T_max 0.9889 _exptl_absorpt_correction_T_min 0.9831 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 292 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.111 _refine_diff_density_min -0.121 _refine_diff_density_rms 0.029 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 2761 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.015 _refine_ls_R_factor_all 0.1232 _refine_ls_R_factor_gt 0.0494 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0931 _refine_ls_wR_factor_ref 0.1090 _reflns_number_gt 1239 _reflns_number_total 2761 _reflns_threshold_expression >2sigma(I) _cod_data_source_file J-Mater-Chem-C-2015-3-10074.cif _cod_data_source_block a _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the built-in table derived from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated on 2014-11-21. data item '_symmetry_cell_setting' value 'Triclinic' was changed to 'triclinic' in accordance with the built-in table derived from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated on 2014-11-21. Automatic conversion script Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas ; _cod_original_cell_volume 793.5(5) _cod_original_sg_symbol_H-M 'P-1 ' _cod_database_code 7234472 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 0.5056(4) 0.7534(2) 0.13391(17) 0.0719(7) Uani 1 1 d . . . H1 H 0.3518 0.7213 0.1135 0.086 Uiso 1 1 calc R . . C2 C 0.6616(5) 0.8105(2) 0.06791(16) 0.0841(8) Uani 1 1 d . . . H2 H 0.6124 0.8171 0.0031 0.101 Uiso 1 1 calc R . . C3 C 0.8891(5) 0.8577(2) 0.09787(19) 0.0812(8) Uani 1 1 d . . . H3 H 0.9937 0.8950 0.0532 0.097 Uiso 1 1 calc R . . C4 C 0.9616(4) 0.8498(2) 0.19318(19) 0.0743(7) Uani 1 1 d . . . H4 H 1.1156 0.8819 0.2132 0.089 Uiso 1 1 calc R . . C5 C 0.8083(4) 0.7945(2) 0.25980(15) 0.0636(6) Uani 1 1 d . . . H5 H 0.8588 0.7910 0.3247 0.076 Uiso 1 1 calc R . . C6 C 0.5794(4) 0.7441(2) 0.23082(15) 0.0567(6) Uani 1 1 d . . . C7 C 0.4235(4) 0.6809(2) 0.30061(15) 0.0630(6) Uani 1 1 d . . . C8 C 0.2990(4) 0.6252(2) 0.35944(15) 0.0607(6) Uani 1 1 d . . . C9 C 0.1484(4) 0.5611(2) 0.43064(15) 0.0536(5) Uani 1 1 d . . . C10 C 0.2287(4) 0.55242(19) 0.52663(16) 0.0600(6) Uani 1 1 d . . . H10 H 0.3831 0.5872 0.5450 0.072 Uiso 1 1 calc R . . C11 C -0.0827(4) 0.5070(2) 0.40510(14) 0.0605(6) Uani 1 1 d . . . H11 H -0.1393 0.5110 0.3410 0.073 Uiso 1 1 calc R . . C12 C 0.5704(4) 0.3675(2) 0.18689(14) 0.0628(6) Uani 1 1 d . . . H12 H 0.4549 0.4110 0.2000 0.075 Uiso 1 1 calc R . . C13 C 0.7303(4) 0.4276(2) 0.12456(15) 0.0735(7) Uani 1 1 d . . . H13 H 0.7220 0.5117 0.0954 0.088 Uiso 1 1 calc R . . C14 C 0.9018(4) 0.3655(3) 0.10475(16) 0.0803(7) Uani 1 1 d . . . H14 H 1.0115 0.4079 0.0634 0.096 Uiso 1 1 calc R . . C15 C 0.9106(4) 0.2398(2) 0.14640(16) 0.0788(7) Uani 1 1 d . . . H15 H 1.0253 0.1963 0.1321 0.095 Uiso 1 1 calc R . . C16 C 0.7520(4) 0.1779(2) 0.20879(14) 0.0665(6) Uani 1 1 d . . . H16 H 0.7597 0.0929 0.2366 0.080 Uiso 1 1 calc R . . C17 C 0.5809(4) 0.2414(2) 0.23051(14) 0.0548(6) Uani 1 1 d . . . C18 C 0.4225(4) 0.1793(2) 0.29980(15) 0.0605(6) Uani 1 1 d . . . C19 C 0.2998(4) 0.1276(2) 0.36065(15) 0.0604(6) Uani 1 1 d . . . C20 C 0.1492(4) 0.0641(2) 0.43183(14) 0.0530(5) Uani 1 1 d . . . C21 C -0.0288(4) 0.1208(2) 0.45596(14) 0.0607(6) Uani 1 1 d . . . H21 H -0.0491 0.2024 0.4265 0.073 Uiso 1 1 calc R . . C22 C 0.1757(3) -0.0581(2) 0.47722(14) 0.0594(6) Uani 1 1 d . . . H22 H 0.2943 -0.0976 0.4621 0.071 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 C1 0.0754(18) 0.0792(16) 0.0631(16) -0.0022(14) 0.0043(14) 0.0229(14) C2 0.110(2) 0.0920(19) 0.0556(16) 0.0071(14) 0.0136(17) 0.0334(18) C3 0.097(2) 0.0652(16) 0.084(2) 0.0110(15) 0.0350(17) 0.0164(15) C4 0.0728(18) 0.0587(14) 0.091(2) 0.0018(14) 0.0123(16) 0.0125(13) C5 0.0707(17) 0.0551(13) 0.0638(15) 0.0024(12) 0.0039(14) 0.0133(12) C6 0.0669(17) 0.0499(13) 0.0550(15) 0.0000(12) 0.0077(13) 0.0168(12) C7 0.0724(17) 0.0565(14) 0.0626(15) 0.0015(13) 0.0096(14) 0.0194(12) C8 0.0668(16) 0.0550(14) 0.0629(15) -0.0001(12) 0.0097(13) 0.0187(12) C9 0.0609(16) 0.0463(12) 0.0562(15) 0.0021(11) 0.0087(12) 0.0170(11) C10 0.0555(15) 0.0573(13) 0.0669(15) 0.0008(12) 0.0027(13) 0.0133(11) C11 0.0639(17) 0.0624(13) 0.0547(14) 0.0009(12) -0.0009(13) 0.0158(12) C12 0.0687(17) 0.0548(13) 0.0667(15) 0.0051(12) 0.0109(12) 0.0165(12) C13 0.092(2) 0.0586(14) 0.0716(16) 0.0136(13) 0.0166(15) 0.0175(14) C14 0.085(2) 0.0860(18) 0.0721(17) 0.0167(15) 0.0299(14) 0.0183(15) C15 0.0834(19) 0.0853(17) 0.0781(17) 0.0160(15) 0.0272(15) 0.0343(15) C16 0.0816(18) 0.0610(14) 0.0624(15) 0.0104(12) 0.0178(13) 0.0243(13) C17 0.0637(16) 0.0497(13) 0.0490(13) -0.0002(11) 0.0064(11) 0.0094(11) C18 0.0657(16) 0.0544(14) 0.0606(15) -0.0021(12) 0.0070(13) 0.0128(12) C19 0.0639(16) 0.0558(14) 0.0607(15) -0.0009(12) 0.0088(13) 0.0116(12) C20 0.0569(15) 0.0485(13) 0.0517(13) -0.0007(11) 0.0078(11) 0.0083(11) C21 0.0714(16) 0.0508(13) 0.0626(15) 0.0060(11) 0.0108(12) 0.0181(12) C22 0.0607(15) 0.0591(14) 0.0635(15) 0.0025(12) 0.0140(12) 0.0218(11) 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' 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 C2 C1 C6 119.8(2) . . C2 C1 H1 120.1 . . C6 C1 H1 120.1 . . C3 C2 C1 120.2(2) . . C3 C2 H2 119.9 . . C1 C2 H2 119.9 . . C4 C3 C2 120.1(2) . . C4 C3 H3 120.0 . . C2 C3 H3 120.0 . . C3 C4 C5 120.4(2) . . C3 C4 H4 119.8 . . C5 C4 H4 119.8 . . C4 C5 C6 120.4(2) . . C4 C5 H5 119.8 . . C6 C5 H5 119.8 . . C5 C6 C1 119.1(2) . . C5 C6 C7 119.6(2) . . C1 C6 C7 121.3(2) . . C8 C7 C6 177.6(2) . . C7 C8 C9 178.7(2) . . C10 C9 C11 118.36(19) . . C10 C9 C8 121.1(2) . . C11 C9 C8 120.6(2) . . C11 C10 C9 120.8(2) 2_566 . C11 C10 H10 119.6 2_566 . C9 C10 H10 119.6 . . C10 C11 C9 120.8(2) 2_566 . C10 C11 H11 119.6 2_566 . C9 C11 H11 119.6 . . C13 C12 C17 120.0(2) . . C13 C12 H12 120.0 . . C17 C12 H12 120.0 . . C14 C13 C12 120.8(2) . . C14 C13 H13 119.6 . . C12 C13 H13 119.6 . . C13 C14 C15 119.4(2) . . C13 C14 H14 120.3 . . C15 C14 H14 120.3 . . C16 C15 C14 120.7(2) . . C16 C15 H15 119.7 . . C14 C15 H15 119.7 . . C15 C16 C17 120.3(2) . . C15 C16 H16 119.9 . . C17 C16 H16 119.9 . . C16 C17 C12 118.90(19) . . C16 C17 C18 119.8(2) . . C12 C17 C18 121.3(2) . . C19 C18 C17 176.7(2) . . C18 C19 C20 178.7(2) . . C21 C20 C22 118.33(18) . . C21 C20 C19 121.0(2) . . C22 C20 C19 120.6(2) . . C22 C21 C20 120.88(19) 2_556 . C22 C21 H21 119.6 2_556 . C20 C21 H21 119.6 . . C21 C22 C20 120.79(19) 2_556 . C21 C22 H22 119.6 2_556 . C20 C22 H22 119.6 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 C2 1.384(3) . C1 C6 1.390(3) . C1 H1 0.9300 . C2 C3 1.375(3) . C2 H2 0.9300 . C3 C4 1.366(3) . C3 H3 0.9300 . C4 C5 1.375(3) . C4 H4 0.9300 . C5 C6 1.383(3) . C5 H5 0.9300 . C6 C7 1.436(3) . C7 C8 1.193(2) . C8 C9 1.434(3) . C9 C10 1.389(2) . C9 C11 1.390(3) . C10 C11 1.375(3) 2_566 C10 H10 0.9300 . C11 C10 1.375(3) 2_566 C11 H11 0.9300 . C12 C13 1.371(3) . C12 C17 1.392(2) . C12 H12 0.9300 . C13 C14 1.367(3) . C13 H13 0.9300 . C14 C15 1.374(3) . C14 H14 0.9300 . C15 C16 1.371(3) . C15 H15 0.9300 . C16 C17 1.380(3) . C16 H16 0.9300 . C17 C18 1.438(3) . C18 C19 1.196(2) . C19 C20 1.432(3) . C20 C21 1.386(2) . C20 C22 1.393(2) . C21 C22 1.373(3) 2_556 C21 H21 0.9300 . C22 C21 1.373(3) 2_556 C22 H22 0.9300 . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C6 C1 C2 C3 0.2(3) . . . . C1 C2 C3 C4 -0.8(3) . . . . C2 C3 C4 C5 0.1(3) . . . . C3 C4 C5 C6 1.1(3) . . . . C4 C5 C6 C1 -1.6(3) . . . . C4 C5 C6 C7 177.13(18) . . . . C2 C1 C6 C5 1.0(3) . . . . C2 C1 C6 C7 -177.74(18) . . . . C5 C6 C7 C8 -54(6) . . . . C1 C6 C7 C8 125(5) . . . . C6 C7 C8 C9 144(9) . . . . C7 C8 C9 C10 -90(11) . . . . C7 C8 C9 C11 90(11) . . . . C11 C9 C10 C11 -0.7(3) . . . 2_566 C8 C9 C10 C11 178.86(17) . . . 2_566 C10 C9 C11 C10 0.7(3) . . . 2_566 C8 C9 C11 C10 -178.86(17) . . . 2_566 C17 C12 C13 C14 -0.3(3) . . . . C12 C13 C14 C15 1.3(3) . . . . C13 C14 C15 C16 -1.2(3) . . . . C14 C15 C16 C17 0.0(3) . . . . C15 C16 C17 C12 1.0(3) . . . . C15 C16 C17 C18 -176.8(2) . . . . C13 C12 C17 C16 -0.9(3) . . . . C13 C12 C17 C18 176.9(2) . . . . C16 C17 C18 C19 53(4) . . . . C12 C17 C18 C19 -125(3) . . . . C17 C18 C19 C20 -149(9) . . . . C18 C19 C20 C21 -82(10) . . . . C18 C19 C20 C22 97(10) . . . . C22 C20 C21 C22 -0.1(3) . . . 2_556 C19 C20 C21 C22 178.68(19) . . . 2_556 C21 C20 C22 C21 0.1(3) . . . 2_556 C19 C20 C22 C21 -178.68(19) . . . 2_556