#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:52:15 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301804 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/43/2214399.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_2214399 loop_ _publ_author_name 'Harrison, William T. A.' 'H. J. Ravindra' 'M. R. Suresh Kumar' 'S. M. Dharmaprakash' _publ_section_title (2E,2'E)-3,3'-(1,4-Phenylene)bis[1-(3,4-dimethoxyphenyl)prop-2-en-1-one] _journal_coeditor_code TK2159 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3068 _journal_page_last o3068 _journal_paper_doi 10.1107/S1600536807026281 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C28 H26 O6' _chemical_formula_moiety 'C28 H26 O6' _chemical_formula_sum 'C28 H26 O6' _chemical_formula_weight 458.48 _chemical_name_systematic ; (2E,2'E)-3,3'-(1,4-Phenylene)bis[1-(3,4-methoxyphenyl)prop-2-en-1-one] ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 111.015(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 10.6974(9) _cell_length_b 10.4056(9) _cell_length_c 11.0337(9) _cell_measurement_reflns_used 2493 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 27.27 _cell_measurement_theta_min 4.39 _cell_volume 1146.50(17) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.978 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area-detector' _diffrn_measurement_method \w _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 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6150 _diffrn_reflns_theta_full 27.57 _diffrn_reflns_theta_max 27.57 _diffrn_reflns_theta_min 4.53 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_description slab _exptl_crystal_F_000 484 _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.28 _refine_diff_density_max 0.140 _refine_diff_density_min -0.233 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 156 _refine_ls_number_reflns 2593 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0419 _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^)+(0.0581P)^2^+0.102P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1062 _refine_ls_wR_factor_ref 0.1171 _reflns_number_gt 1845 _reflns_number_total 2593 _reflns_threshold_expression I>2\s(I) _cod_data_source_file tk2159.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2214399 _cod_database_fobs_code 2214399 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' 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_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy C C1 0.02570(14) 0.62724(13) 0.98401(14) 0.0531(4) Uani d . 1 H H1 0.0426 0.7134 0.9735 0.064 Uiso calc R 1 C C2 0.06430(13) 0.53394(12) 0.91311(12) 0.0458(3) Uani d . 1 C C3 0.03669(14) 0.40569(13) 0.93106(14) 0.0543(4) Uani d . 1 H H3 0.0608 0.3416 0.8849 0.065 Uiso calc R 1 C C4 0.13242(13) 0.57377(13) 0.82596(13) 0.0492(3) Uani d . 1 H H4 0.1527 0.6608 0.8269 0.059 Uiso calc R 1 C C5 0.16902(14) 0.50108(13) 0.74548(14) 0.0520(3) Uani d . 1 H H5 0.1510 0.4134 0.7409 0.062 Uiso calc R 1 C C6 0.23769(14) 0.55662(13) 0.66305(14) 0.0522(3) Uani d . 1 C C7 0.24029(13) 0.48429(12) 0.54784(13) 0.0480(3) Uani d . 1 C C8 0.16721(13) 0.37084(12) 0.50367(13) 0.0488(3) Uani d . 1 H H8 0.1149 0.3380 0.5479 0.059 Uiso calc R 1 C C9 0.17175(13) 0.30731(13) 0.39578(13) 0.0480(3) Uani d . 1 C C10 0.25223(13) 0.35637(14) 0.32880(13) 0.0497(3) Uani d . 1 C C11 0.32134(15) 0.46974(14) 0.37027(15) 0.0567(4) Uani d . 1 H H11 0.3720 0.5041 0.3250 0.068 Uiso calc R 1 C C12 0.31592(15) 0.53259(14) 0.47846(15) 0.0561(4) Uani d . 1 H H12 0.3636 0.6085 0.5055 0.067 Uiso calc R 1 C C13 0.01953(17) 0.14495(16) 0.40800(18) 0.0678(4) Uani d . 1 H H13A -0.0219 0.0676 0.3645 0.102 Uiso calc R 1 H H13B -0.0484 0.2067 0.4043 0.102 Uiso calc R 1 H H13C 0.0716 0.1260 0.4970 0.102 Uiso calc R 1 C C14 0.34061(18) 0.32855(19) 0.16052(17) 0.0758(5) Uani d . 1 H H14A 0.3366 0.2690 0.0927 0.114 Uiso calc R 1 H H14B 0.4312 0.3346 0.2207 0.114 Uiso calc R 1 H H14C 0.3109 0.4116 0.1235 0.114 Uiso calc R 1 O O1 0.29246(12) 0.66240(10) 0.68998(12) 0.0766(4) Uani d . 1 O O2 0.10457(11) 0.19627(10) 0.34583(11) 0.0651(3) Uani d . 1 O O3 0.25563(10) 0.28434(11) 0.22740(10) 0.0629(3) Uani d . 1 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 0.0634(9) 0.0385(7) 0.0622(8) -0.0027(6) 0.0285(7) -0.0062(6) C2 0.0445(7) 0.0438(7) 0.0477(7) 0.0000(5) 0.0148(6) -0.0045(5) C3 0.0655(9) 0.0433(7) 0.0609(8) -0.0002(6) 0.0311(7) -0.0108(6) C4 0.0506(7) 0.0428(7) 0.0547(8) -0.0004(6) 0.0196(6) -0.0022(6) C5 0.0585(8) 0.0417(7) 0.0610(8) -0.0018(6) 0.0278(7) -0.0023(6) C6 0.0536(8) 0.0422(7) 0.0668(9) 0.0002(6) 0.0287(7) -0.0003(6) C7 0.0497(7) 0.0412(7) 0.0576(8) 0.0022(6) 0.0249(6) 0.0044(6) C8 0.0500(7) 0.0453(7) 0.0586(8) -0.0011(6) 0.0286(6) 0.0045(6) C9 0.0450(7) 0.0449(7) 0.0568(8) -0.0017(5) 0.0216(6) 0.0023(6) C10 0.0490(7) 0.0548(8) 0.0480(7) 0.0026(6) 0.0205(6) 0.0052(6) C11 0.0615(8) 0.0566(8) 0.0624(9) -0.0058(7) 0.0347(7) 0.0075(7) C12 0.0610(8) 0.0455(7) 0.0683(9) -0.0090(6) 0.0312(7) 0.0016(7) C13 0.0689(10) 0.0598(9) 0.0853(11) -0.0209(8) 0.0404(9) -0.0075(8) C14 0.0750(11) 0.1011(14) 0.0658(10) -0.0157(10) 0.0426(9) -0.0087(9) O1 0.0974(9) 0.0538(7) 0.1000(9) -0.0231(6) 0.0612(7) -0.0188(6) O2 0.0719(7) 0.0612(6) 0.0760(7) -0.0203(5) 0.0433(6) -0.0156(5) O3 0.0667(6) 0.0735(7) 0.0580(6) -0.0107(5) 0.0339(5) -0.0067(5) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle C3 C1 C2 3_567 121.41(13) C3 C1 H1 3_567 119.3 C2 C1 H1 . 119.3 C3 C2 C1 . 117.65(12) C3 C2 C4 . 123.09(12) C1 C2 C4 . 119.25(12) C1 C3 C2 3_567 120.94(12) C1 C3 H3 3_567 119.5 C2 C3 H3 . 119.5 C5 C4 C2 . 127.99(13) C5 C4 H4 . 116.0 C2 C4 H4 . 116.0 C4 C5 C6 . 121.34(12) C4 C5 H5 . 119.3 C6 C5 H5 . 119.3 O1 C6 C5 . 119.98(13) O1 C6 C7 . 120.36(12) C5 C6 C7 . 119.65(12) C12 C7 C8 . 118.30(13) C12 C7 C6 . 118.72(12) C8 C7 C6 . 122.96(12) C9 C8 C7 . 121.06(12) C9 C8 H8 . 119.5 C7 C8 H8 . 119.5 O2 C9 C8 . 125.26(12) O2 C9 C10 . 115.10(12) C8 C9 C10 . 119.64(12) O3 C10 C11 . 125.13(12) O3 C10 C9 . 115.60(12) C11 C10 C9 . 119.26(13) C10 C11 C12 . 120.53(12) C10 C11 H11 . 119.7 C12 C11 H11 . 119.7 C11 C12 C7 . 121.16(13) C11 C12 H12 . 119.4 C7 C12 H12 . 119.4 O2 C13 H13A . 109.5 O2 C13 H13B . 109.5 H13A C13 H13B . 109.5 O2 C13 H13C . 109.5 H13A C13 H13C . 109.5 H13B C13 H13C . 109.5 O3 C14 H14A . 109.5 O3 C14 H14B . 109.5 H14A C14 H14B . 109.5 O3 C14 H14C . 109.5 H14A C14 H14C . 109.5 H14B C14 H14C . 109.5 C9 O2 C13 . 117.16(11) C10 O3 C14 . 117.09(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance C1 C3 3_567 1.3746(19) C1 C2 . 1.3988(18) C1 H1 . 0.9300 C2 C3 . 1.3962(19) C2 C4 . 1.4594(18) C3 C1 3_567 1.3746(19) C3 H3 . 0.9300 C4 C5 . 1.3279(18) C4 H4 . 0.9300 C5 C6 . 1.4765(18) C5 H5 . 0.9300 C6 O1 . 1.2322(17) C6 C7 . 1.4861(19) C7 C12 . 1.3918(18) C7 C8 . 1.4033(18) C8 C9 . 1.3777(19) C8 H8 . 0.9300 C9 O2 . 1.3679(16) C9 C10 . 1.4157(18) C10 O3 . 1.3580(16) C10 C11 . 1.380(2) C11 C12 . 1.380(2) C11 H11 . 0.9300 C12 H12 . 0.9300 C13 O2 . 1.4250(17) C13 H13A . 0.9600 C13 H13B . 0.9600 C13 H13C . 0.9600 C14 O3 . 1.4366(18) C14 H14A . 0.9600 C14 H14B . 0.9600 C14 H14C . 0.9600 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_site_symmetry_4 _geom_torsion C3 C1 C2 C3 3_567 . 0.3(2) C3 C1 C2 C4 3_567 . -178.89(12) C1 C2 C3 C1 . 3_567 -0.3(2) C4 C2 C3 C1 . 3_567 178.86(13) C3 C2 C4 C5 . . 5.4(2) C1 C2 C4 C5 . . -175.49(14) C2 C4 C5 C6 . . 179.98(13) C4 C5 C6 O1 . . 18.6(2) C4 C5 C6 C7 . . -161.43(13) O1 C6 C7 C12 . . 5.9(2) C5 C6 C7 C12 . . -174.11(13) O1 C6 C7 C8 . . -172.50(14) C5 C6 C7 C8 . . 7.5(2) C12 C7 C8 C9 . . 1.1(2) C6 C7 C8 C9 . . 179.53(12) C7 C8 C9 O2 . . 179.78(12) C7 C8 C9 C10 . . 0.5(2) O2 C9 C10 O3 . . -2.31(18) C8 C9 C10 O3 . . 177.00(12) O2 C9 C10 C11 . . 178.49(12) C8 C9 C10 C11 . . -2.2(2) O3 C10 C11 C12 . . -176.94(13) C9 C10 C11 C12 . . 2.2(2) C10 C11 C12 C7 . . -0.5(2) C8 C7 C12 C11 . . -1.2(2) C6 C7 C12 C11 . . -179.64(13) C8 C9 O2 C13 . . 2.3(2) C10 C9 O2 C13 . . -178.43(13) C11 C10 O3 C14 . . 1.6(2) C9 C10 O3 C14 . . -177.53(13) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 90655480