#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202457.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_2202457 loop_ _publ_author_name ' Lee, Ting Wai ' ' Lau, Jasmine Po Kwan' ' Szeto, Lap ' _publ_section_title ; Diphenic acid--4,4'-bipyridine (2/1) ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o942 _journal_page_last o944 _journal_paper_doi 10.1107/S1600536803012194 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C28 H20 O8, C10 H8 N2' _chemical_formula_sum 'C38 H28 N2 O8' _chemical_formula_weight 640.62 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method 'from TEXRAY.INF file' _cell_angle_alpha 99.45(5) _cell_angle_beta 100.93(3) _cell_angle_gamma 98.42(5) _cell_formula_units_Z 1 _cell_length_a 6.498(2) _cell_length_b 8.002(7) _cell_length_c 16.208(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 16.3 _cell_measurement_theta_min 13.2 _cell_volume 802.4(8) _computing_cell_refinement 'AFC Diffractometer Control' _computing_data_collection 'AFC Diffractometer Control (Molecular Structure Corporation, 1992)' _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1992)' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device AFC7R _diffrn_measurement_method '\w/2-\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.016 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 3049 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 2.16 _diffrn_standards_decay_% -0.91 _diffrn_standards_interval_count 250 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.957 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 334.00 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _refine_diff_density_max 0.30 _refine_diff_density_min -0.27 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.306 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 225 _refine_ls_number_reflns 2830 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1087 _refine_ls_R_factor_gt 0.0361 _refine_ls_shift/su_max <0.001 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'calc w = 1/[(\s)^2^(Fo)+0.00016(Fo)^2^]' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.0538 _reflns_number_gt 1448 _reflns_number_total 2830 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6221.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_atom_site_thermal_displace_type' tag value 'Uij' was replaced with 'Uani' value 38 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana ; _cod_original_sg_symbol_H-M 'P -1 ' _cod_original_formula_sum 'C38 H28 N2 O8 ' _cod_database_code 2202457 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' 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 O1 0.0720(10) 0.0580(10) 0.0710(10) 0.0196(9) -0.0139(9) 0.0136(9) O2 0.0920(10) 0.0410(10) 0.115(2) 0.0108(10) -0.0280(10) 0.0200(10) O3 0.0640(10) 0.0660(10) 0.0630(10) 0.0035(9) 0.0230(9) -0.0095(9) O4 0.0700(10) 0.0520(10) 0.0700(10) -0.0044(9) 0.0312(9) -0.0003(9) N1 0.074(2) 0.074(2) 0.0670(10) 0.0280(10) 0.0010(10) 0.0210(10) C1 0.0560(10) 0.0430(10) 0.0500(10) 0.0170(10) 0.0090(10) 0.0100(10) C2 0.0510(10) 0.0400(10) 0.0400(10) 0.0120(10) 0.0130(10) 0.0083(10) C3 0.064(2) 0.0450(10) 0.0540(10) 0.0080(10) 0.0060(10) 0.0090(10) C4 0.088(2) 0.0390(10) 0.064(2) 0.0060(10) 0.0100(10) 0.0080(10) C5 0.093(2) 0.0430(10) 0.068(2) 0.0230(10) 0.012(2) 0.0200(10) C6 0.067(2) 0.0520(10) 0.0520(10) 0.0220(10) 0.0050(10) 0.0140(10) C7 0.0500(10) 0.0410(10) 0.0410(10) 0.0120(10) 0.0140(10) 0.0094(10) C8 0.0460(10) 0.0470(10) 0.0450(10) 0.0130(10) 0.0080(10) 0.0180(10) C9 0.054(2) 0.066(2) 0.0570(10) 0.0120(10) 0.0180(10) 0.0160(10) C10 0.053(2) 0.077(2) 0.073(2) 0.0000(10) 0.0140(10) 0.030(2) C11 0.059(2) 0.059(2) 0.070(2) -0.0070(10) 0.0020(10) 0.0160(10) C12 0.057(2) 0.0490(10) 0.0560(10) 0.0050(10) 0.0050(10) 0.0080(10) C13 0.0440(10) 0.0440(10) 0.0420(10) 0.0100(10) 0.0040(10) 0.0094(10) C14 0.0470(10) 0.0450(10) 0.0410(10) 0.0100(10) 0.0040(10) 0.0050(10) C15 0.088(2) 0.107(2) 0.074(2) 0.037(2) 0.020(2) 0.050(2) C16 0.075(2) 0.105(2) 0.081(2) 0.044(2) 0.029(2) 0.047(2) C17 0.0530(10) 0.064(2) 0.0440(10) 0.0150(10) 0.0020(10) 0.0130(10) C18 0.110(2) 0.093(2) 0.074(2) 0.054(2) 0.044(2) 0.036(2) C19 0.106(2) 0.089(2) 0.084(2) 0.051(2) 0.035(2) 0.025(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O1 1.1226(3) 0.6029(2) 0.36520(10) 0.0703(6) Uani ? ? O2 0.8605(3) 0.4039(2) 0.28360(10) 0.0895(7) Uani ? ? O3 0.8094(3) 0.3251(2) -0.00250(10) 0.0666(6) Uani ? ? O4 0.8892(3) 0.5837(2) 0.08160(10) 0.0651(6) Uani ? ? N1 0.7048(4) 0.6498(3) 0.57330(10) 0.0713(8) Uani ? ? C1 0.9452(4) 0.5522(3) 0.30540(10) 0.0495(7) Uani ? ? C2 0.8630(3) 0.6970(3) 0.27110(10) 0.0431(6) Uani ? ? C3 0.9730(4) 0.8641(3) 0.30420(10) 0.0557(7) Uani ? ? C4 0.8981(4) 1.0036(3) 0.2778(2) 0.0650(8) Uani ? ? C5 0.7092(5) 0.9766(3) 0.2186(2) 0.0663(9) Uani ? ? C6 0.5989(4) 0.8119(3) 0.18440(10) 0.0566(7) Uani ? ? C7 0.6748(3) 0.6686(3) 0.20780(10) 0.0430(6) Uani ? ? C8 0.5456(3) 0.4946(3) 0.16490(10) 0.0449(6) Uani ? ? C9 0.3618(4) 0.4401(3) 0.19230(10) 0.0579(8) Uani ? ? C10 0.2305(4) 0.2831(4) 0.1550(2) 0.0671(9) Uani ? ? C11 0.2781(4) 0.1768(3) 0.0886(2) 0.0658(8) Uani ? ? C12 0.4556(4) 0.2291(3) 0.05860(10) 0.0558(7) Uani ? ? C13 0.5910(3) 0.3871(3) 0.09530(10) 0.0439(6) Uani ? ? C14 0.7746(3) 0.4365(3) 0.05640(10) 0.0455(7) Uani ? ? C15 0.5568(5) 0.7174(4) 0.6042(2) 0.0830(10) Uani ? ? C16 0.4722(4) 0.8523(4) 0.5777(2) 0.0790(10) Uani ? ? C17 0.5414(4) 0.9248(3) 0.51460(10) 0.0539(7) Uani ? ? C18 0.6927(5) 0.8521(4) 0.4809(2) 0.0830(10) Uani ? ? C19 0.7694(5) 0.7169(4) 0.5118(2) 0.0860(10) Uani ? ? H1 1.177(5) 0.499(4) 0.388(2) 0.130(10) Uani ? ? H2 0.973(6) 0.369(4) -0.038(2) 0.160(10) Uani ? ? H3 1.1026 0.8829 0.3459 0.0669 Uani ? ? H4 0.9764 1.1171 0.3005 0.0780 Uani ? ? H5 0.6544 1.0721 0.2011 0.0795 Uani ? ? H6 0.4678 0.7955 0.1438 0.0679 Uani ? ? H7 0.3253 0.5124 0.2379 0.0695 Uani ? ? H8 0.1065 0.2486 0.1755 0.0806 Uani ? ? H9 0.1890 0.0682 0.0637 0.0789 Uani ? ? H10 0.4872 0.1564 0.0118 0.0669 Uani ? ? H11 0.5043 0.6699 0.6479 0.1002 Uani ? ? H12 0.3655 0.8955 0.6032 0.0953 Uani ? ? H13 0.7454 0.8947 0.4361 0.0995 Uani ? ? H14 0.8749 0.6697 0.4872 0.1037 Uani ? ? loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.003 0.002 'International Tables' O 0.011 0.006 'International Tables' N 0.006 0.003 'International Tables' H 0.000 0.000 'International Tables' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 -1 4 -2 0 4 1 1 3 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_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 O1 H1 ? ? 111.0(10) no C14 O3 H2 ? ? 117.0(10) no C15 N1 C19 ? ? 115.8(2) no O1 C1 O2 ? ? 121.9(2) no O1 C1 C2 ? ? 113.2(2) no O2 C1 C2 ? ? 124.9(2) no C1 C2 C3 ? ? 119.0(2) no C1 C2 C7 ? ? 121.5(2) no C3 C2 C7 ? ? 119.4(2) no C2 C3 C4 ? ? 121.4(2) no C2 C3 H3 ? ? 119.3 no C4 C3 H3 ? ? 119.3 no C3 C4 C5 ? ? 119.2(2) no C3 C4 H4 ? ? 120.4 no C5 C4 H4 ? ? 120.4 no C4 C5 C6 ? ? 120.2(2) no C4 C5 H5 ? ? 119.9 no C6 C5 H5 ? ? 119.9 no C5 C6 C7 ? ? 121.6(2) no C5 C6 H6 ? ? 119.2 no C7 C6 H6 ? ? 119.2 no C2 C7 C6 ? ? 118.0(2) no C2 C7 C8 ? ? 124.6(2) no C6 C7 C8 ? ? 117.4(2) no C7 C8 C9 ? ? 117.8(2) no C7 C8 C13 ? ? 124.4(2) no C9 C8 C13 ? ? 117.7(2) no C8 C9 C10 ? ? 121.6(2) no C8 C9 H7 ? ? 119.2 no C10 C9 H7 ? ? 119.2 no C9 C10 C11 ? ? 120.5(2) no C9 C10 H8 ? ? 119.7 no C11 C10 H8 ? ? 119.8 no C10 C11 C12 ? ? 119.3(2) no C10 C11 H9 ? ? 120.4 no C12 C11 H9 ? ? 120.4 no C11 C12 C13 ? ? 121.3(2) no C11 C12 H10 ? ? 119.3 no C13 C12 H10 ? ? 119.3 no C8 C13 C12 ? ? 119.6(2) no C8 C13 C14 ? ? 122.7(2) no C12 C13 C14 ? ? 117.7(2) no O3 C14 O4 ? ? 122.2(2) no O3 C14 C13 ? ? 117.5(2) no O4 C14 C13 ? ? 120.2(2) no N1 C15 C16 ? ? 124.3(3) no N1 C15 H11 ? ? 117.8 no C16 C15 H11 ? ? 117.8 no C15 C16 C17 ? ? 120.2(3) no C15 C16 H12 ? ? 119.9 no C17 C16 H12 ? ? 119.9 no C16 C17 C17 ? 2_676 122.1(3) no C16 C17 C18 ? ? 115.6(2) no C17 C17 C18 2_676 ? 122.3(3) no C17 C18 C19 ? ? 120.3(2) no C17 C18 H13 ? ? 119.8 no C19 C18 H13 ? ? 119.8 no N1 C19 C18 ? ? 123.8(3) no N1 C19 H14 ? ? 118.1 no C18 C19 H14 ? ? 118.1 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 ? ? 1.321(3) yes O1 H1 ? ? 1.04(3) no O2 C1 ? ? 1.197(3) yes O3 C14 ? ? 1.272(2) yes O3 H2 ? ? 1.33(4) no O4 C14 ? ? 1.256(2) yes N1 C15 ? ? 1.309(3) yes N1 C19 ? ? 1.313(3) yes C1 C2 ? ? 1.489(3) yes C2 C3 ? ? 1.388(3) no C2 C7 ? ? 1.402(3) no C3 C4 ? ? 1.379(3) no C3 H3 ? ? 0.95 no C4 C5 ? ? 1.372(3) no C4 H4 ? ? 0.95 no C5 C6 ? ? 1.375(3) no C5 H5 ? ? 0.95 no C6 C7 ? ? 1.393(3) no C6 H6 ? ? 0.95 no C7 C8 ? ? 1.498(3) yes C8 C9 ? ? 1.389(3) no C8 C13 ? ? 1.408(3) no C9 C10 ? ? 1.383(3) no C9 H7 ? ? 0.95 no C10 C11 ? ? 1.370(4) no C10 H8 ? ? 0.95 no C11 C12 ? ? 1.372(3) no C11 H9 ? ? 0.95 no C12 C13 ? ? 1.399(3) no C12 H10 ? ? 0.95 no C13 C14 ? ? 1.486(3) yes C15 C16 ? ? 1.375(4) yes C15 H11 ? ? 0.95 no C16 C17 ? ? 1.370(3) yes C16 H12 ? ? 0.95 no C17 C17 ? 2_676 1.497(4) yes C17 C18 ? ? 1.368(3) yes C18 C19 ? ? 1.382(4) yes C18 H13 ? ? 0.95 no C19 H14 ? ? 0.95 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O3 H2 O4 2_765 1.33(4) 1.29(4) 2.618(3) 171(3) O1 H1 N1 2_766 1.04(3) 1.65(3) 2.691(4) 172(3) C4 H4 O2 1_565 0.95 2.56 3.235(4) 128 C6 H6 O3 2_665 0.95 2.57 3.472(4) 158 C3 H3 O1 . 0.95 2.33 2.683(4) 101 C12 H10 O3 . 0.95 2.39 2.730(4) 100 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139066039