#------------------------------------------------------------------------------
#$Date: 2025-08-19 08:12:48 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/86/2018600.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_2018600
loop_
_publ_author_name
'Tutughamiarso, Maya'
'Pisternick, Thorsten'
'Egert, Ernst'
_publ_section_title
;
 Pseudopolymorphs of chelidamic acid and its dimethyl ester
;
_journal_coeditor_code           EG3095
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o344
_journal_page_last               o350
_journal_paper_doi               10.1107/S0108270112031691
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C7 H5 N O5, C H4 O'
_chemical_formula_moiety         'C7 H5 N O5, C H4 O'
_chemical_formula_sum            'C8 H9 N O6'
_chemical_formula_weight         215.16
_chemical_name_common
;
chelidamic acid methanol monosolvate
;
_chemical_name_systematic
;
4-hydroxypyridine-2,6-dicarboxylic acid methanol monosolvate
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.303(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8256(5)
_cell_length_b                   12.5648(12)
_cell_length_c                   12.7464(11)
_cell_measurement_reflns_used    12422
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      3.24
_cell_volume                     917.96(14)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics
'Mercury (Macrae et al., 2008) and XP (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       ω
_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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8713
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.56
_diffrn_reflns_theta_min         3.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0521P)²+0.3671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                1491
_reflns_number_total             1712
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            eg3095.cif
_cod_data_source_block           Ia
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2018600
_cod_database_fobs_code          2018600
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
_atom_site_symmetry_multiplicity
N N1 0.6359(2) 0.63208(10) 0.45800(9) 0.0174(3) Uani d . 1 1
H H1 0.760(4) 0.6038(17) 0.4439(16) 0.037(5) Uiso d . 1 1
C C2 0.4981(2) 0.68738(11) 0.37964(11) 0.0170(3) Uani d . 1 1
C C3 0.2995(3) 0.73542(11) 0.39842(11) 0.0183(3) Uani d . 1 1
H H3 0.2024 0.7731 0.3428 0.022 Uiso calc R 1 1
C C4 0.2381(3) 0.72914(11) 0.50048(11) 0.0181(3) Uani d . 1 1
C C5 0.3849(3) 0.66925(11) 0.58014(11) 0.0182(3) Uani d . 1 1
H H5 0.3469 0.6617 0.6492 0.022 Uiso calc R 1 1
C C6 0.5812(3) 0.62263(11) 0.55661(11) 0.0171(3) Uani d . 1 1
C C21 0.5859(3) 0.69354(11) 0.27464(11) 0.0174(3) Uani d . 1 1
O O21 0.44112(19) 0.72881(9) 0.19653(8) 0.0246(3) Uani d . 1 1
O O22 0.79039(19) 0.66493(9) 0.27627(8) 0.0252(3) Uani d . 1 1
O O41 0.04962(18) 0.77874(9) 0.51697(8) 0.0219(3) Uani d . 1 1
H H41 0.021(5) 0.774(2) 0.597(2) 0.064(7) Uiso d . 1 1
C C61 0.7573(3) 0.56000(11) 0.63437(11) 0.0187(3) Uani d . 1 1
O O61 0.9366(2) 0.52961(9) 0.60839(8) 0.0266(3) Uani d . 1 1
O O62 0.69101(19) 0.54420(9) 0.72637(8) 0.0230(3) Uani d . 1 1
H H62 0.825(5) 0.505(2) 0.775(2) 0.065(7) Uiso d . 1 1
C C1M 1.1971(3) 0.52753(15) 0.89663(16) 0.0395(5) Uani d . 1 1
H H1M1 1.1487 0.5720 0.9519 0.059 Uiso calc R 1 1
H H1M2 1.2307 0.5728 0.8386 0.059 Uiso calc R 1 1
H H1M3 1.3374 0.4875 0.9273 0.059 Uiso calc R 1 1
O O1M 1.0126(2) 0.45452(9) 0.85558(9) 0.0273(3) Uani d . 1 1
H H1M 1.077(4) 0.403(2) 0.8130(19) 0.055(7) Uiso d . 1 1
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
C2 N1 C6 121.45(13)
C2 N1 H1 118.1(14)
C6 N1 H1 120.4(14)
N1 C2 C3 120.45(13)
N1 C2 C21 115.30(13)
C3 C2 C21 124.23(13)
C2 C3 C4 119.98(13)
C2 C3 H3 120.0
C4 C3 H3 120.0
O41 C4 C3 118.57(13)
O41 C4 C5 123.47(13)
C3 C4 C5 117.96(14)
C6 C5 C4 119.42(13)
C6 C5 H5 120.3
C4 C5 H5 120.3
N1 C6 C5 120.72(13)
N1 C6 C61 114.14(13)
C5 C6 C61 125.13(13)
O22 C21 O21 128.17(14)
O22 C21 C2 116.38(12)
O21 C21 C2 115.45(12)
C4 O41 H41 114.1(14)
O61 C61 O62 126.96(13)
O61 C61 C6 120.06(13)
O62 C61 C6 112.98(13)
C61 O62 H62 107.2(15)
O1M C1M H1M1 109.5
O1M C1M H1M2 109.5
H1M1 C1M H1M2 109.5
O1M C1M H1M3 109.5
H1M1 C1M H1M3 109.5
H1M2 C1M H1M3 109.5
C1M O1M H1M 107.0(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3556(19)
N1 C6 1.3559(19)
N1 H1 0.86(2)
C2 C3 1.364(2)
C2 C21 1.5179(19)
C3 C4 1.412(2)
C3 H3 0.9500
C4 O41 1.3118(18)
C4 C5 1.421(2)
C5 C6 1.365(2)
C5 H5 0.9500
C6 C61 1.513(2)
C21 O22 1.2409(19)
C21 O21 1.2644(18)
O41 H41 1.07(3)
C61 O61 1.2124(19)
C61 O62 1.3136(18)
O62 H62 1.03(3)
C1M O1M 1.439(2)
C1M H1M1 0.9800
C1M H1M2 0.9800
C1M H1M3 0.9800
O1M H1M 0.97(3)
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
N1 H1 O61 3_766 0.86(2) 2.61(2) 3.4354(18) 163.7(19)
O41 H41 O21 4_576 1.07(3) 1.43(3) 2.4827(14) 170(2)
O62 H62 O1M . 1.03(3) 1.50(3) 2.5274(15) 174(3)
O1M H1M O22 3_766 0.97(3) 1.71(3) 2.6617(16) 167(2)
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
C6 N1 C2 C3 0.1(2)
C6 N1 C2 C21 178.30(12)
N1 C2 C3 C4 1.0(2)
C21 C2 C3 C4 -177.04(13)
C2 C3 C4 O41 178.04(13)
C2 C3 C4 C5 -1.9(2)
O41 C4 C5 C6 -178.22(13)
C3 C4 C5 C6 1.7(2)
C2 N1 C6 C5 -0.3(2)
C2 N1 C6 C61 -178.86(12)
C4 C5 C6 N1 -0.6(2)
C4 C5 C6 C61 177.79(13)
N1 C2 C21 O22 -12.50(19)
C3 C2 C21 O22 165.63(14)
N1 C2 C21 O21 168.44(13)
C3 C2 C21 O21 -13.4(2)
N1 C6 C61 O61 5.00(19)
C5 C6 C61 O61 -173.51(14)
N1 C6 C61 O62 -174.55(12)
C5 C6 C61 O62 6.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654383
2 PubChem 139061373
