#------------------------------------------------------------------------------ #$Date: 2025-07-01 14:00:44 +0300 (Tue, 01 Jul 2025) $ #$Revision: 1165 $ #$URL: svn://localhost/testcod/cif/2/00/00/2000033.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_2000033 loop_ _publ_author_name 'Solovyov, Leonid A.' _publ_section_title ; Accurate unrestrained DDM refinement of crystal structures from highly distorted and low-resolution powder diffraction data ; _journal_coeditor_code RA5013 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials' _journal_page_first 738 _journal_page_last 743 _journal_paper_doi 10.1107/S2052520616011690 _journal_volume 72 _journal_year 2016 _chemical_formula_moiety 'C4 H4 O4, C4 H2 O4, 2(C5 H7 N2)' _chemical_formula_sum 'C18 H20 N4 O8' _chemical_formula_weight 420.38 _chemical_name_systematic ; Bis(2-aminopyridinium) fumarate--fumaric acid (1/1) ; _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_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_type_scat_source ; X-Ray Form Factor, C Attenuation and Scattering Tables (version 2.1). NIST, Gaithersburg, MD. ; _cell_angle_alpha 94.2993(6) _cell_angle_beta 91.7434(6) _cell_angle_gamma 91.7142(7) _cell_formula_units_Z 1 _cell_length_a 3.81737(6) _cell_length_b 9.60821(16) _cell_length_c 13.36297(24) _cell_measurement_reflns_used 413 _cell_measurement_temperature 298 _cell_measurement_theta_max 35 _cell_measurement_theta_min 2.5 _cell_volume 488.268(14) _computing_structure_refinement ; Powder diffraction, Derivative Difference Method (DDM) L.A. Solovyov, J. Appl. Cryst. 37 (2004) 743 ; _diffrn_ambient_temperature 298 _diffrn_measurement_device_type 'Rigaku SmartLab diffractometer' _diffrn_radiation_probe x-ray _exptl_crystal_density_diffrn 1.4302 _pd_block_id profile_II _pd_char_colour yellow _pd_meas_2theta_range_inc 0.0200 _pd_meas_2theta_range_max 70.0000 _pd_meas_2theta_range_min 5.0000 _pd_meas_scan_method cont _pd_proc_ls_prof_wR_expected 0.02265 _pd_proc_ls_prof_wR_factor 0.06807 _pd_spec_mounting 'borosilicate capillary' _pd_spec_mount_mode transmission _pd_spec_shape cylinder _refine_ls_goodness_of_fit_all 1.73354 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 107 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.03942 _refine_ls_R_I_factor 0.02784 _refine_ls_shift/su_max 0.00971 _publcif_datablock.id {dda7f230-76b6-4c4f-a124-188677e9c317} _publcif_info_exptl_table_max_cols 4 _publcif_info_exptl_table_use_headnotes n _cod_data_source_file ra5013sup1.cif _cod_data_source_block II _cod_original_sg_symbol_Hall '-P 1 ' _cod_original_sg_symbol_H-M 'P -1 ' _cod_original_formula_sum 'C18 H20 N4 O8 ' _cod_database_code 2000033 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 'x, y, z' 2 '-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_occupancy _atom_site_adp_type O1 O 0.2564(13) 0.47822(40) 0.20517(32) 0.0665(20) 1.0000 Uani O2 O 0.1137(13) 0.28934(49) 0.10168(36) 0.0690(25) 1.0000 Uani O3 O 0.0968(16) 0.23872(43) 0.48573(34) 0.0664(30) 1.0000 Uani O4 O 0.2729(13) 0.30780(48) 0.34060(31) 0.0515(20) 1.0000 Uani N1 N 0.4783(17) 0.0553(6) 0.26054(45) 0.0594(25) 1.0000 Uiso N2 N 0.2651(16) -0.0337(5) 0.40143(29) 0.0577(25) 1.0000 Uiso C1 C 0.4089(17) -0.0581(9) 0.3132(5) 0.0474(32) 1.0000 Uiso C2 C 0.4937(19) -0.1933(7) 0.27389(45) 0.0500(29) 1.0000 Uiso C3 C 0.6441(17) -0.2043(7) 0.1829(6) 0.0498(27) 1.0000 Uiso C4 C 0.7017(18) -0.0906(7) 0.1248(5) 0.0515(30) 1.0000 Uiso C5 C 0.6171(17) 0.0365(7) 0.1674(5) 0.0626(30) 1.0000 Uiso C6 C 0.1555(21) 0.4152(8) 0.1188(6) 0.0379(37) 1.0000 Uiso C7 C 0.0909(18) 0.5168(9) 0.04328(40) 0.0463(29) 1.0000 Uiso C8 C 0.1342(27) 0.3321(9) 0.4268(7) 0.0493(41) 1.0000 Uiso C9 C 0.0483(19) 0.4786(7) 0.45532(44) 0.0426(31) 1.0000 Uiso H1 H 0.26268 0.41766 0.25335 0.0760 1.0000 Uiso H21 H 0.45008 -0.27346 0.30966 0.0760 1.0000 Uiso H31 H 0.71321 -0.29361 0.15684 0.0760 1.0000 Uiso H41 H 0.79130 -0.10171 0.05918 0.0760 1.0000 Uiso H51 H 0.66053 0.11683 0.13167 0.0760 1.0000 Uiso H11 H 0.43005 0.14159 0.28629 0.0760 1.0000 Uiso H91 H 0.06142 0.54431 0.40571 0.0760 1.0000 Uiso H71 H 0.18505 0.60930 0.05596 0.0760 1.0000 Uiso H22 H 0.21358 0.05192 0.42781 0.0760 1.0000 Uiso H23 H 0.15097 -0.09758 0.43481 0.0760 1.0000 Uiso 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 0.110(5) 0.0499(44) 0.0389(43) 0.0023(45) -0.0182(41) 0.0046(42) O2 0.095(5) 0.0270(42) 0.0801(46) -0.0126(47) -0.0138(38) -0.0182(41) O3 0.131(6) 0.0155(39) 0.057(6) 0.0169(40) 0.0340(41) 0.0117(35) O4 0.0720(49) 0.0363(39) 0.0490(45) 0.0197(33) 0.0272(39) 0.0044(40) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag O 0.04549 0.03199 N 0.02875 0.01803 C 0.01612 0.00904 H -0.00053 0.00000 loop_ _diffrn_radiation_wavelength _diffrn_radiation_wavelength_wt 1.5406 1.0000 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 _geom_angle_publ_flag C1 N1 C5 119.4(6) . . ? N1 C1 N2 116.6(7) . . ? N1 C1 C2 120.3(6) . . ? N2 C1 C2 123.1(7) . . ? C1 C2 C3 117.4(6) . . ? C2 C3 C4 123.5(6) . . ? C3 C4 C5 116.0(6) . . ? N1 C5 C4 123.2(7) . . ? O1 C6 O2 125.3(7) . . ? O1 C6 C7 111.1(6) . . ? O2 C6 C7 123.6(7) . . ? C6 C7 C7 122.6(10) . 2_565 ? O3 C8 O4 121.6(7) . . ? O3 C8 C9 121.6(8) . . ? O4 C8 C9 116.6(7) . . ? C8 C9 C9 123.1(9) . 2_566 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.365(11) . ? N1 C5 1.369(9) . ? C1 N2 1.323(8) . ? C1 C2 1.414(11) . ? C2 C3 1.358(10) . ? C3 C4 1.403(10) . ? C4 C5 1.360(10) . ? C6 C7 1.477(11) . ? C7 C7 1.344(11) 2_565 ? C8 C9 1.480(11) . ? C9 C9 1.301(12) 2_566 ? C6 O1 1.305(9) . ? C6 O2 1.218(9) . ? C8 O3 1.245(10) . ? C8 O4 1.291(10) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O1 H1 O4 0.9000 1.6300 2.530(6) 180.00 . yes N1 H11 O4 0.9000 1.8300 2.724(7) 172.00 . yes N2 H22 O3 0.9000 1.9700 2.870(6) 180.00 . yes N2 H23 O3 0.9000 2.0200 2.911(7) 178.00 2_556 yes 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 _geom_torsion_publ_flag C5 N1 C1 C2 2.7(10) . . . . no C1 N1 C5 C4 -2.2(10) . . . . no C5 N1 C1 N2 -178.0(6) . . . . no O2 C6 C7 C7 14.9(11) . . . 2_565 no O1 C6 C7 C7 -163.9(7) . . . 2_565 no C6 C7 C7 C6 180.0(7) . . 2_565 2_565 no O3 C8 C9 C9 4.6(14) . . . 2_566 no O4 C8 C9 C9 -170.5(8) . . . 2_566 no C8 C9 C9 C8 180.0(9) . . 2_566 2_566 no N1 C1 C2 C3 -0.1(10) . . . . no N2 C1 C2 C3 -179.3(6) . . . . no C1 C2 C3 C4 -3.3(10) . . . . no C2 C3 C4 C5 3.9(10) . . . . no C3 C4 C5 N1 -1.1(10) . . . . no loop_ _publcif_info_cif.paper_type CB loop_ _publcif_info_datablock.id _publcif_info_datablock.publ_exptl _publcif_info_datablock.publ_geom _publcif_info_datablock.structure {84186d0e-b744-4d4f-b271-21af9bf5340d} y y y {dda7f230-76b6-4c4f-a124-188677e9c317} y y y loop_ _publcif_info_exptl_table_extra_item ? loop_ _publcif_info_exptl_table_header_item ? loop_ _publcif_info_tables.block_id _publcif_info_tables.reference_item {84186d0e-b744-4d4f-b271-21af9bf5340d} '_publcif_info_datablock.publ_exptl' {dda7f230-76b6-4c4f-a124-188677e9c317} '_geom_hbond_atom_site_label_D'