#------------------------------------------------------------------------------
#$Date: 2021-05-15 07:50:02 +0300 (Sat, 15 May 2021) $
#$Revision: 265246 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243832.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_2243832
loop_
_publ_author_name
'Behrman, Edward J.'
'Parkin, Sean'
_publ_section_title
;
 Synthesis and crystal structures of 3,6-dihydroxypicolinic acid and its
 labile intermediate dipotassium
 3-hydroxy-6-(sulfonatooxy)pyridine-2-carboxylate monohydrate
;
_journal_coeditor_code           HB7975
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              623
_journal_page_last               628
_journal_paper_doi               10.1107/S2056989021004904
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C6 H5 N O4'
_chemical_formula_moiety         'C6 H5 N O4'
_chemical_formula_sum            'C6 H5 N O4'
_chemical_formula_weight         155.11
_chemical_name_common
;
3,6-Dihydroxypicolinic acid
;
_chemical_name_systematic
;
3-Hydroxy-6-oxo-1,6-dihydropyridine-2-carboxylic acid
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           39
_space_group_name_Hall           'A 2 -2b'
_space_group_name_H-M_alt        'A e m 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2045(6)
_cell_length_b                   6.1282(4)
_cell_length_c                   9.7293(6)
_cell_measurement_reflns_used    3820
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      78.48
_cell_measurement_theta_min      4.33
_cell_volume                     608.42(7)
_computing_cell_refinement
;
APEX3 (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
APEX3 (Bruker, 2016)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4025
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.820
_diffrn_reflns_theta_min         4.332
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.270
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.251
_refine_ls_abs_structure_details
;
Refined as a perfect inversion twin
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         700
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0243
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0500P)²+0.0512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0675
_reflns_number_gt                690
_reflns_number_total             700
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7975sup1.cif
_cod_data_source_block           II
_cod_original_sg_symbol_Hall     'A 2 -2c'
_cod_original_sg_symbol_H-M      'A b m 2'
_cod_database_code               2243832
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.842
_shelx_estimated_absorpt_t_max   0.975
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x, -y+1/2, z'
'-x, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x, -y+1, z+1/2'
'-x, y+1, 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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.3327(2) 0.250000 0.44103(19) 0.0146(4) Uani d 0.953(3) A 1
H H1N 0.421(3) 0.25000(2) 0.3976(15) 0.017 Uiso calc 0.953(3) A 1
C C2 0.3260(2) 0.250000 0.5827(2) 0.0131(5) Uani d 0.953(3) A 1
C C3 0.2033(3) 0.250000 0.6458(3) 0.0148(5) Uani d 0.953(3) A 1
O O1 0.19022(19) 0.250000 0.7831(2) 0.0188(4) Uani d 0.953(3) A 1
H H1O 0.269(4) 0.25000(2) 0.8219(19) 0.028 Uiso calc 0.953(3) A 1
C C4 0.0919(3) 0.250000 0.5626(3) 0.0194(6) Uani d 0.953(3) A 1
H H4 0.007769 0.250000 0.604343 0.023 Uiso calc 0.953(3) A 1
C C5 0.1011(2) 0.250000 0.4226(3) 0.0191(5) Uani d 0.953(3) A 1
H H5 0.024166 0.250000 0.367711 0.023 Uiso calc 0.953(3) A 1
C C6 0.2280(2) 0.250000 0.3592(3) 0.0154(5) Uani d 0.953(3) A 1
O O2 0.2369(2) 0.250000 0.22580(18) 0.0186(4) Uani d 0.953(3) A 1
H H2O 0.326(3) 0.25000(2) 0.2000(10) 0.028 Uiso calc 0.953(3) A 1
C C7 0.4488(2) 0.250000 0.6616(2) 0.0158(5) Uani d 0.953(3) A 1
O O3 0.55590(18) 0.250000 0.59684(19) 0.0182(4) Uani d 0.953(3) A 1
O O4 0.43850(17) 0.250000 0.7906(2) 0.0224(5) Uani d 0.953(3) A 1
N N1' 0.3327(2) 0.250000 0.55897(19) 0.0131(5) Uani d 0.047(3) A 2
H H1'N 0.421(3) 0.25000(2) 0.6024(16) 0.016 Uiso calc 0.047(3) A 2
C C2' 0.3260(2) 0.250000 0.4173(2) 0.0146(4) Uani d 0.047(3) A 2
C C3' 0.2033(3) 0.250000 0.3542(3) 0.0154(5) Uani d 0.047(3) A 2
O O1' 0.19022(19) 0.250000 0.2169(2) 0.0186(4) Uani d 0.047(3) A 2
H H1'O 0.269(4) 0.25000(2) 0.178(2) 0.028 Uiso calc 0.047(3) A 2
C C4' 0.0919(3) 0.250000 0.4374(3) 0.0191(5) Uani d 0.047(3) A 2
H H4' 0.007769 0.250000 0.395657 0.023 Uiso calc 0.047(3) A 2
C C5' 0.1011(2) 0.250000 0.5774(3) 0.0194(6) Uani d 0.047(3) A 2
H H5' 0.024166 0.250000 0.632289 0.023 Uiso calc 0.047(3) A 2
C C6' 0.2280(2) 0.250000 0.6408(3) 0.0148(5) Uani d 0.047(3) A 2
O O2' 0.2369(2) 0.250000 0.77420(18) 0.0188(4) Uani d 0.047(3) A 2
H H2'O 0.326(4) 0.25000(2) 0.8001(11) 0.028 Uiso calc 0.047(3) A 2
C C7' 0.4488(2) 0.250000 0.3384(2) 0.0158(5) Uani d 0.047(3) A 2
O O3' 0.55590(18) 0.250000 0.40316(19) 0.0182(4) Uani d 0.047(3) A 2
O O4' 0.43850(17) 0.250000 0.2094(2) 0.0224(5) Uani d 0.047(3) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 C2 . . 123.81(19) ?
C6 N1 H1N . . 118.1 ?
C2 N1 H1N . . 118.1 ?
N1 C2 C3 . . 119.0(2) ?
N1 C2 C7 . . 118.6(2) ?
C3 C2 C7 . . 122.41(19) ?
O1 C3 C2 . . 121.8(2) ?
O1 C3 C4 . . 119.8(2) ?
C2 C3 C4 . . 118.4(2) ?
C3 O1 H1O . . 109.5 ?
C5 C4 C3 . . 121.5(2) ?
C5 C4 H4 . . 119.2 ?
C3 C4 H4 . . 119.2 ?
C4 C5 C6 . . 119.5(2) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
O2 C6 N1 . . 122.7(2) ?
O2 C6 C5 . . 119.5(2) ?
N1 C6 C5 . . 117.8(2) ?
C6 O2 H2O . . 109.5 ?
O4 C7 O3 . . 124.8(2) ?
O4 C7 C2 . . 116.7(2) ?
O3 C7 C2 . . 118.53(19) ?
C6' N1' C2' . . 123.81(19) ?
C6' N1' H1'N . . 118.1 ?
C2' N1' H1'N . . 118.1 ?
N1' C2' C3' . . 119.0(2) ?
N1' C2' C7' . . 118.6(2) ?
C3' C2' C7' . . 122.41(19) ?
O1' C3' C2' . . 121.8(2) ?
O1' C3' C4' . . 119.8(2) ?
C2' C3' C4' . . 118.4(2) ?
C3' O1' H1'O . . 109.5 ?
C5' C4' C3' . . 121.5(2) ?
C5' C4' H4' . . 119.2 ?
C3' C4' H4' . . 119.2 ?
C4' C5' C6' . . 119.5(2) ?
C4' C5' H5' . . 120.3 ?
C6' C5' H5' . . 120.3 ?
O2' C6' N1' . . 122.7(2) ?
O2' C6' C5' . . 119.5(2) ?
N1' C6' C5' . . 117.8(2) ?
C6' O2' H2'O . . 109.5 ?
O4' C7' O3' . . 124.8(2) ?
O4' C7' C2' . . 116.7(2) ?
O3' C7' C2' . . 118.53(19) ?
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
N1 C6 . 1.333(3) ?
N1 C2 . 1.381(3) ?
N1 H1N . 0.99(3) ?
C2 C3 . 1.394(3) ?
C2 C7 . 1.470(3) ?
C3 O1 . 1.342(3) ?
C3 C4 . 1.395(4) ?
O1 H1O . 0.89(4) ?
C4 C5 . 1.365(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.434(3) ?
C5 H5 . 0.9500 ?
C6 O2 . 1.301(3) ?
O2 H2O . 0.94(4) ?
C7 O4 . 1.259(3) ?
C7 O3 . 1.262(3) ?
N1' C6' . 1.333(3) ?
N1' C2' . 1.381(3) ?
N1' H1'N . 0.99(4) ?
C2' C3' . 1.394(3) ?
C2' C7' . 1.470(3) ?
C3' O1' . 1.342(3) ?
C3' C4' . 1.395(4) ?
O1' H1'O . 0.89(4) ?
C4' C5' . 1.365(3) ?
C4' H4' . 0.9500 ?
C5' C6' . 1.434(3) ?
C5' H5' . 0.9500 ?
C6' O2' . 1.301(3) ?
O2' H2'O . 0.94(4) ?
C7' O4' . 1.259(3) ?
C7' O3' . 1.262(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
_geom_hbond_publ_flag
N1 H1N O4 6_654 0.99 1.77 2.755(3) 169 yes
O1 H1O O4 . 0.89 1.76 2.535(3) 145 yes
C5 H5 O1 6_554 0.95 2.34 3.269(3) 166 yes
C4 H4 O2 6 0.95 2.76 3.712(4) 180 yes
O2 H2O O3 6_654 0.94 1.57 2.459(3) 156 yes
O2 H2O O4 6_654 0.94 2.56 3.372(3) 144 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C2 C3 . . . . 0.0000(10) ?
C6 N1 C2 C7 . . . . 180.000000 ?
N1 C2 C3 O1 . . . . 180.000000 ?
C7 C2 C3 O1 . . . . 0.0000(10) ?
N1 C2 C3 C4 . . . . 0.0000(10) ?
C7 C2 C3 C4 . . . . 180.0000(10) ?
O1 C3 C4 C5 . . . . 180.0000(10) ?
C2 C3 C4 C5 . . . . 0.0000(10) ?
C3 C4 C5 C6 . . . . 0.0000(10) ?
C2 N1 C6 O2 . . . . 180.000000 ?
C2 N1 C6 C5 . . . . 0.000000 ?
C4 C5 C6 O2 . . . . 180.000000 ?
C4 C5 C6 N1 . . . . 0.000000 ?
N1 C2 C7 O4 . . . . 180.000000 ?
C3 C2 C7 O4 . . . . 0.0000(10) ?
N1 C2 C7 O3 . . . . 0.000000 ?
C3 C2 C7 O3 . . . . 180.000000 ?
C6' N1' C2' C3' . . . . 0.000000 ?
C6' N1' C2' C7' . . . . 180.000000 ?
N1' C2' C3' O1' . . . . 180.000000 ?
C7' C2' C3' O1' . . . . 0.000000 ?
N1' C2' C3' C4' . . . . 0.000000 ?
C7' C2' C3' C4' . . . . 180.000000 ?
O1' C3' C4' C5' . . . . 180.000000 ?
C2' C3' C4' C5' . . . . 0.000000 ?
C3' C4' C5' C6' . . . . 0.000000 ?
C2' N1' C6' O2' . . . . 180.000000 ?
C2' N1' C6' C5' . . . . 0.0000(10) ?
C4' C5' C6' O2' . . . . 180.000000 ?
C4' C5' C6' N1' . . . . 0.0000(10) ?
N1' C2' C7' O4' . . . . 180.000000 ?
C3' C2' C7' O4' . . . . 0.000000 ?
N1' C2' C7' O3' . . . . 0.000000 ?
C3' C2' C7' O3' . . . . 180.000000 ?

_cod_database_fobs_code 2243832
