#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/31/2013142.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2013142 loop_ _publ_author_name 'Perera, K. Prasanna U.' 'Abboud, Khalil A.' 'Smith Jr, Dennis W.' 'Krawiec, Mariusz' _publ_section_title ; Three bis-ortho-diynylarenes (BODA) ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o107 _journal_page_last o110 _journal_paper_doi 10.1107/S0108270102023594 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C44 H26' _chemical_formula_moiety 'C44 H26' _chemical_formula_sum 'C44 H26' _chemical_formula_weight 554.65 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 92.540(15) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 13.299(7) _cell_length_b 5.229(3) _cell_length_c 21.196(11) _cell_measurement_reflns_used 3530 _cell_measurement_temperature 300(2) _cell_measurement_theta_max 26.47 _cell_measurement_theta_min 0.96 _cell_volume 1472.5(14) _computing_cell_refinement CrystalClear _computing_data_collection 'CrystalClear (Rigaku, 1998-2001)' _computing_data_reduction CrystalClear _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXTL (Bruker. 1998)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 300(2) _diffrn_detector_area_resol_mean 7.314 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.09143 _diffrn_reflns_av_sigmaI/netI 0.0971 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 14417 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_full 26.48 _diffrn_reflns_theta_max 26.48 _diffrn_reflns_theta_min 2.51 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_T_min 0.987 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_meas ? _exptl_crystal_description platelet _exptl_crystal_F_000 580.00 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.181 _refine_diff_density_min -0.178 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 3021 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.149 _refine_ls_R_factor_all 0.1780 _refine_ls_R_factor_gt 0.0788 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0608P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1353 _refine_ls_wR_factor_ref 0.1821 _reflns_number_gt 1664 _reflns_number_total 3021 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fr1389.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 1472.4(14) _cod_database_code 2013142 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y,1/2-z' ' -x, -y, -z' ' +x,1/2-y,1/2+z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.0200(2) 0.4834(6) 0.96801(15) 0.0323(7) Uani d . 1 . . C C2 0.0893(2) 0.2930(6) 0.95569(15) 0.0352(7) Uani d . 1 . . C H2 0.1096 0.1832 0.9883 0.042 Uiso calc R 1 . . H C3 0.1296(2) 0.2591(6) 0.89687(15) 0.0336(7) Uani d . 1 . . C C4 0.0985(2) 0.4236(6) 0.84734(14) 0.0358(8) Uani d . 1 . . C C5 0.0272(2) 0.6120(6) 0.85877(16) 0.0399(8) Uani d . 1 . . C H5 0.0048 0.7191 0.8260 0.048 Uiso calc R 1 . . H C6 -0.0104(2) 0.6414(6) 0.91780(15) 0.0373(8) Uani d . 1 . . C H6 -0.0573 0.7697 0.9244 0.045 Uiso calc R 1 . . H C7 0.2030(2) 0.0641(7) 0.88780(14) 0.0384(8) Uani d . 1 . . C C8 0.2659(2) -0.0997(6) 0.88176(15) 0.0378(8) Uani d . 1 . . C C9 0.3399(2) -0.2945(6) 0.87416(15) 0.0339(7) Uani d . 1 . . C C10 0.3742(2) -0.4486(6) 0.92376(16) 0.0409(8) Uani d . 1 . . C H10 0.3497 -0.4242 0.9638 0.049 Uiso calc R 1 . . H C11 0.4446(2) -0.6385(7) 0.91435(17) 0.0442(9) Uani d . 1 . . C H11 0.4669 -0.7413 0.9479 0.053 Uiso calc R 1 . . H C12 0.4816(2) -0.6753(6) 0.85530(17) 0.0419(9) Uani d . 1 . . C H12 0.5288 -0.8030 0.8488 0.050 Uiso calc R 1 . . H C13 0.4482(2) -0.5215(6) 0.80574(17) 0.0429(8) Uani d . 1 . . C H13 0.4732 -0.5458 0.7658 0.051 Uiso calc R 1 . . H C14 0.3782(2) -0.3319(6) 0.81492(16) 0.0393(8) Uani d . 1 . . C H14 0.3565 -0.2287 0.7813 0.047 Uiso calc R 1 . . H C15 0.1405(2) 0.4116(7) 0.78612(16) 0.0392(8) Uani d . 1 . . C C16 0.1763(2) 0.4203(7) 0.73519(16) 0.0406(8) Uani d . 1 . . C C17 0.2190(2) 0.4426(6) 0.67546(14) 0.0349(7) Uani d . 1 . . C C18 0.2918(2) 0.2725(7) 0.65654(16) 0.0426(8) Uani d . 1 . . C H18 0.3141 0.1430 0.6838 0.051 Uiso calc R 1 . . H C19 0.3314(3) 0.2930(7) 0.59811(16) 0.0455(9) Uani d . 1 . . C H19 0.3803 0.1777 0.5860 0.055 Uiso calc R 1 . . H C20 0.2992(2) 0.4831(7) 0.55715(16) 0.0437(8) Uani d . 1 . . C H20 0.3257 0.4952 0.5173 0.052 Uiso calc R 1 . . H C21 0.2279(2) 0.6544(7) 0.57506(17) 0.0431(8) Uani d . 1 . . C H21 0.2065 0.7833 0.5474 0.052 Uiso calc R 1 . . H C22 0.1875(2) 0.6373(6) 0.63388(16) 0.0413(8) Uani d . 1 . . C H22 0.1395 0.7552 0.6458 0.050 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0273(14) 0.0376(16) 0.0321(16) -0.0031(13) 0.0026(12) -0.0055(14) C2 0.0335(16) 0.0390(17) 0.0334(17) 0.0007(14) 0.0027(14) -0.0010(15) C3 0.0291(15) 0.0379(17) 0.0339(17) -0.0017(14) 0.0041(13) -0.0077(15) C4 0.0282(15) 0.046(2) 0.0336(18) -0.0030(14) 0.0036(13) -0.0069(15) C5 0.0406(18) 0.0456(19) 0.0333(18) 0.0062(15) 0.0013(14) 0.0034(16) C6 0.0366(17) 0.0414(19) 0.0342(18) 0.0065(14) 0.0041(14) -0.0003(15) C7 0.0391(17) 0.0456(19) 0.0311(18) -0.0015(16) 0.0082(14) -0.0096(16) C8 0.0349(16) 0.0427(18) 0.0362(18) -0.0044(15) 0.0072(14) -0.0088(16) C9 0.0271(15) 0.0344(16) 0.0405(19) -0.0014(13) 0.0054(14) -0.0070(15) C10 0.0425(18) 0.0413(19) 0.0396(19) -0.0039(16) 0.0096(15) -0.0027(16) C11 0.0439(19) 0.0409(19) 0.048(2) -0.0003(15) 0.0006(17) 0.0036(16) C12 0.0333(17) 0.0395(19) 0.053(2) 0.0030(14) 0.0049(16) -0.0059(17) C13 0.0393(17) 0.0452(19) 0.045(2) 0.0011(16) 0.0117(15) -0.0118(17) C14 0.0385(17) 0.0416(18) 0.0380(19) 0.0008(15) 0.0050(15) -0.0044(16) C15 0.0342(17) 0.046(2) 0.038(2) -0.0019(15) 0.0052(15) -0.0068(16) C16 0.0394(18) 0.047(2) 0.0350(19) 0.0005(15) 0.0031(16) -0.0047(16) C17 0.0350(16) 0.0431(18) 0.0267(16) -0.0054(15) 0.0017(13) -0.0047(15) C18 0.0477(19) 0.0421(19) 0.0381(19) 0.0060(16) 0.0019(16) 0.0063(16) C19 0.049(2) 0.051(2) 0.037(2) 0.0089(17) 0.0114(16) -0.0012(17) C20 0.0477(19) 0.054(2) 0.0296(17) -0.0048(17) 0.0035(15) 0.0026(16) C21 0.0410(18) 0.0458(19) 0.043(2) 0.0029(16) 0.0015(16) 0.0086(17) C22 0.0365(17) 0.0427(19) 0.045(2) 0.0040(15) 0.0054(15) -0.0018(17) 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_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 C1 C6 . 117.1(3) yes C2 C1 C1 3_567 121.4(4) yes C6 C1 C1 3_567 121.6(3) yes C1 C2 C3 . 123.0(3) ? C1 C2 H2 . 118.5 ? C3 C2 H2 . 118.5 ? C2 C3 C4 . 118.6(3) yes C2 C3 C7 . 120.2(3) yes C4 C3 C7 . 121.1(3) yes C5 C4 C3 . 118.9(3) yes C5 C4 C15 . 118.8(3) yes C3 C4 C15 . 122.3(3) yes C6 C5 C4 . 120.9(3) ? C6 C5 H5 . 119.6 ? C4 C5 H5 . 119.6 ? C5 C6 C1 . 121.5(3) ? C5 C6 H6 . 119.2 ? C1 C6 H6 . 119.2 ? C8 C7 C3 . 178.3(3) yes C7 C8 C9 . 179.5(4) yes C10 C9 C14 . 118.8(3) yes C10 C9 C8 . 122.3(3) yes C14 C9 C8 . 118.9(3) yes C11 C10 C9 . 120.7(3) ? C11 C10 H10 . 119.7 ? C9 C10 H10 . 119.7 ? C12 C11 C10 . 120.1(3) ? C12 C11 H11 . 120.0 ? C10 C11 H11 . 120.0 ? C11 C12 C13 . 119.6(3) ? C11 C12 H12 . 120.2 ? C13 C12 H12 . 120.2 ? C14 C13 C12 . 120.6(3) ? C14 C13 H13 . 119.7 ? C12 C13 H13 . 119.7 ? C13 C14 C9 . 120.3(3) ? C13 C14 H14 . 119.8 ? C9 C14 H14 . 119.8 ? C16 C15 C4 . 175.3(4) yes C15 C16 C17 . 177.4(4) yes C18 C17 C22 . 118.6(3) yes C18 C17 C16 . 121.1(3) yes C22 C17 C16 . 120.2(3) yes C19 C18 C17 . 120.7(3) ? C19 C18 H18 . 119.6 ? C17 C18 H18 . 119.6 ? C18 C19 C20 . 120.3(3) ? C18 C19 H19 . 119.8 ? C20 C19 H19 . 119.8 ? C21 C20 C19 . 119.9(3) ? C21 C20 H20 . 120.0 ? C19 C20 H20 . 120.0 ? C20 C21 C22 . 120.5(3) ? C20 C21 H21 . 119.7 ? C22 C21 H21 . 119.7 ? C21 C22 C17 . 119.9(3) ? C21 C22 H22 . 120.1 ? C17 C22 H22 . 120.1 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . 1.388(4) ? C1 C6 . 1.392(4) ? C1 C1 3_567 1.486(6) yes C2 C3 . 1.388(4) ? C2 H2 . 0.9300 ? C3 C4 . 1.404(4) ? C3 C7 . 1.430(4) yes C4 C5 . 1.395(4) ? C4 C15 . 1.435(4) yes C5 C6 . 1.375(4) ? C5 H5 . 0.9300 ? C6 H6 . 0.9300 ? C7 C8 . 1.207(4) yes C8 C9 . 1.430(4) yes C9 C10 . 1.385(4) ? C9 C14 . 1.387(4) ? C10 C11 . 1.384(5) ? C10 H10 . 0.9300 ? C11 C12 . 1.377(5) ? C11 H11 . 0.9300 ? C12 C13 . 1.380(5) ? C12 H12 . 0.9300 ? C13 C14 . 1.379(4) ? C13 H13 . 0.9300 ? C14 H14 . 0.9300 ? C15 C16 . 1.198(4) yes C16 C17 . 1.413(4) yes C17 C18 . 1.386(4) ? C17 C22 . 1.398(4) ? C18 C19 . 1.369(5) ? C18 H18 . 0.9300 ? C19 C20 . 1.375(5) ? C19 H19 . 0.9300 ? C20 C21 . 1.369(5) ? C20 H20 . 0.9300 ? C21 C22 . 1.380(5) ? C21 H21 . 0.9300 ? 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_site_symmetry_1 _geom_torsion C6 C1 C2 C3 . 1.2(4) C1 C1 C2 C3 3_567 -178.8(4) C1 C2 C3 C4 . -0.4(5) C1 C2 C3 C7 . 178.1(3) C2 C3 C4 C5 . -1.1(4) C7 C3 C4 C5 . -179.5(3) C2 C3 C4 C15 . 176.4(3) C7 C3 C4 C15 . -2.1(5) C3 C4 C5 C6 . 1.7(5) C15 C4 C5 C6 . -175.9(3) C4 C5 C6 C1 . -0.8(5) C2 C1 C6 C5 . -0.6(5) C1 C1 C6 C5 3_567 179.4(4) C14 C9 C10 C11 . -0.7(5) C8 C9 C10 C11 . 178.8(3) C9 C10 C11 C12 . 0.3(5) C10 C11 C12 C13 . 0.1(5) C11 C12 C13 C14 . -0.1(5) C12 C13 C14 C9 . -0.4(5) C10 C9 C14 C13 . 0.8(5) C8 C9 C14 C13 . -178.7(3) C22 C17 C18 C19 . -0.7(5) C16 C17 C18 C19 . 178.8(3) C17 C18 C19 C20 . -0.1(5) C18 C19 C20 C21 . 0.6(5) C19 C20 C21 C22 . -0.3(5) C20 C21 C22 C17 . -0.5(5) C18 C17 C22 C21 . 1.0(5) C16 C17 C22 C21 . -178.5(3)