#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/38/2103833.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_2103833 loop_ _publ_author_name 'Bowes, Katharine F.' 'Ferguson, George' 'Lough, Alan J.' 'Glidewell, Christopher' _publ_section_title ; Salts of maleic and fumaric acids with organic polyamines: comparison of isomeric acids as building blocks in supramolecular chemistry ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 100 _journal_page_last 117 _journal_paper_doi 10.1107/S0108768102020219 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C10 H10 N2, 2(C4 H3 O4)' _chemical_formula_sum 'C18 H16 N2 O8' _chemical_formula_weight 388.33 _chemical_name_systematic ; 4,4'-Bipyridyl--maleic acid (1/2) ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 115.996(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 24.0370(16) _cell_length_b 6.7434(6) _cell_length_c 11.4388(10) _cell_measurement_reflns_used 1888 _cell_measurement_temperature 150.0(10) _cell_measurement_theta_max 27.50 _cell_measurement_theta_min 3.51 _cell_volume 1666.5(2) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'Kappa-CCD server software (Nonius, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997b)' _diffrn_ambient_temperature 150.0(10) _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type Kappa-CCD _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.072 _diffrn_reflns_av_sigmaI/netI 0.0672 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6178 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 3.51 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_correction_T_min 0.877 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 808 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.243 _refine_diff_density_min -0.259 _refine_ls_extinction_coef 0.016(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 1888 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0437 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0462P)^2^+1.0798P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1060 _refine_ls_wR_factor_ref 0.1189 _reflns_number_gt 1421 _reflns_number_total 1888 _reflns_threshold_expression >2\s(I) _cod_data_source_file na0143.cif _cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2103833 _cod_database_fobs_code 2103833 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol N11 0.44588(6) 0.2678(2) 0.48738(13) 0.0246(4) Uani d . 1 N C12 0.40590(8) 0.3044(3) 0.36396(16) 0.0257(4) Uani d . 1 C C13 0.42605(8) 0.3131(3) 0.26812(17) 0.0248(4) Uani d . 1 C C14 0.48857(7) 0.2796(3) 0.30091(15) 0.0218(4) Uani d . 1 C C15 0.52904(8) 0.2441(3) 0.43110(16) 0.0239(4) Uani d . 1 C C16 0.50642(8) 0.2395(3) 0.52289(16) 0.0247(4) Uani d . 1 C O1 0.40810(5) 0.2096(2) 0.66811(11) 0.0303(4) Uani d . 1 O O2 0.32715(6) 0.1011(2) 0.49363(11) 0.0316(4) Uani d . 1 O O3 0.22399(5) -0.0399(2) 0.43713(11) 0.0282(3) Uani d . 1 O O4 0.16824(5) -0.1073(2) 0.54247(12) 0.0318(4) Uani d . 1 O C1 0.35393(8) 0.1391(3) 0.61348(16) 0.0243(4) Uani d . 1 C C2 0.32241(8) 0.1016(3) 0.69871(16) 0.0269(4) Uani d . 1 C C3 0.26661(8) 0.0247(3) 0.66884(16) 0.0271(4) Uani d . 1 C C4 0.21652(8) -0.0464(3) 0.54370(16) 0.0246(4) Uani d . 1 C H2 0.3455 0.1379 0.7873 0.032 Uiso calc R 1 H H3 0.2585 0.0110 0.4533 0.042 Uiso calc R 1 H H3A 0.2571 0.0132 0.7409 0.033 Uiso calc R 1 H H11 0.4321 0.2621 0.5470 0.030 Uiso calc R 1 H H12 0.3634 0.3245 0.3421 0.031 Uiso calc R 1 H H13 0.3977 0.3414 0.1808 0.030 Uiso calc R 1 H H15 0.5719 0.2231 0.4562 0.029 Uiso calc R 1 H H16 0.5338 0.2162 0.6116 0.030 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 N11 0.0259(7) 0.0279(9) 0.0250(7) -0.0033(6) 0.0158(6) -0.0023(6) C12 0.0223(8) 0.0302(10) 0.0266(9) -0.0002(7) 0.0127(7) -0.0033(7) C13 0.0205(8) 0.0307(10) 0.0236(8) 0.0006(7) 0.0101(7) -0.0007(7) C14 0.0217(8) 0.0227(9) 0.0226(8) -0.0014(6) 0.0113(7) -0.0006(7) C15 0.0221(8) 0.0265(10) 0.0240(8) -0.0018(7) 0.0110(7) -0.0008(7) C16 0.0248(8) 0.0270(10) 0.0221(8) -0.0031(7) 0.0101(7) 0.0008(7) O1 0.0223(6) 0.0444(9) 0.0256(6) -0.0067(5) 0.0118(5) -0.0028(6) O2 0.0305(7) 0.0463(9) 0.0216(6) -0.0096(6) 0.0146(5) -0.0052(6) O3 0.0252(6) 0.0388(8) 0.0216(6) -0.0065(6) 0.0111(5) -0.0024(5) O4 0.0242(6) 0.0413(9) 0.0315(7) -0.0056(6) 0.0137(5) -0.0016(6) C1 0.0237(8) 0.0267(10) 0.0239(8) -0.0001(7) 0.0117(7) 0.0010(7) C2 0.0253(8) 0.0369(11) 0.0196(8) -0.0010(7) 0.0109(7) -0.0026(7) C3 0.0260(9) 0.0374(11) 0.0214(8) -0.0006(7) 0.0136(7) 0.0013(8) C4 0.0230(8) 0.0258(10) 0.0258(8) 0.0003(7) 0.0115(7) 0.0011(7) 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' N N 0.0061 0.0033 '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_3 _geom_angle _geom_angle_publ_flag C12 N11 C16 . 121.86(14) no C12 N11 H11 . 119.1 no C16 N11 H11 . 119.1 no N11 C12 C13 . 120.43(15) no N11 C12 H12 . 119.8 no C13 C12 H12 . 119.8 no C12 C13 C14 . 119.34(16) no C12 C13 H13 . 120.3 no C14 C13 H13 . 120.3 no C15 C14 C13 . 118.54(14) no C15 C14 C14 2_655 120.68(17) no C13 C14 C14 2_655 120.77(18) no C16 C15 C14 . 119.54(15) no C16 C15 H15 . 120.2 no C14 C15 H15 . 120.2 no N11 C16 C15 . 120.25(16) no N11 C16 H16 . 119.9 no C15 C16 H16 . 119.9 no C4 O3 H3 . 109.5 no O2 C1 O1 . 122.61(15) no O2 C1 C2 . 120.80(15) no O1 C1 C2 . 116.58(15) no C3 C2 C1 . 129.64(16) no C3 C2 H2 . 115.2 no C1 C2 H2 . 115.2 no C2 C3 C4 . 132.01(15) no C2 C3 H3A . 114.0 no C4 C3 H3A . 114.0 no O4 C4 O3 . 121.09(16) no O4 C4 C3 . 118.79(15) no O3 C4 C3 . 120.10(14) no 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 N11 C12 . 1.337(2) no N11 C16 . 1.342(2) no N11 H11 . 0.88 no C12 C13 . 1.380(2) no C12 H12 . 0.95 no C13 C14 . 1.398(2) no C13 H13 . 0.95 no C14 C15 . 1.397(2) no C14 C14 2_655 1.490(3) no C15 C16 . 1.378(2) no C15 H15 . 0.95 no C16 H16 . 0.95 no O1 C1 . 1.264(2) no O2 C1 . 1.259(2) no O3 C4 . 1.309(2) no O3 H3 . 0.84 no O4 C4 . 1.225(2) no C1 C2 . 1.495(2) no C2 C3 . 1.335(2) no C2 H2 . 0.95 no C3 C4 . 1.489(2) no C3 H3A . 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 _geom_hbond_publ_flag N11 H11 O1 . 0.88 1.75 2.627(2) 171 y O3 H3 O2 . 0.84 1.62 2.463(2) 176 y C13 H13 O4 4 0.95 2.37 3.315(2) 175 y C15 H15 O4 3 0.95 2.38 3.176(2) 142 y C16 H16 O1 2_656 0.95 2.28 3.223(2) 170 y 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 _geom_torsion_publ_flag C16 N11 C12 C13 . . 0.4(3) no N11 C12 C13 C14 . . 1.1(3) no C12 C13 C14 C15 . . -1.8(3) no C12 C13 C14 C14 . 2_655 177.47(13) no C13 C14 C15 C16 . . 1.1(3) no C14 C14 C15 C16 2_655 . -178.24(13) no C12 N11 C16 C15 . . -1.2(3) no C14 C15 C16 N11 . . 0.4(3) no O2 C1 C2 C3 . . 1.7(3) no O1 C1 C2 C3 . . -178.2(2) no C1 C2 C3 C4 . . -1.2(4) no C2 C3 C4 O4 . . -178.3(2) no C2 C3 C4 O3 . . 0.5(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139063796