Synthesis and crystal structures of 3,6-dihydroxypicolinic acid and its labile intermediate dipotassium 3-hydroxy-6-(sulfonatooxy)pyridine-2-carboxylate monohydrate
Behrman, Edward J.; Parkin, Sean; Acta Crystallographica Section E 77 (2021) 623–628; doi:10.1107/S2056989021004904

data_2243832
_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
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>XP</i> in <i>SHELXTL</i> (Sheldrick, 2008)
;
_computing_publication_material
;
<i>SHELX</i> (Sheldrick, 2008) and <i>CIFFIX</i> (Parkin, 2013)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT</i> (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       '\f and \w 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
;
(<i>SADABS</i>; Krause <i>et al.</i>,  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/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0512P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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
_cod_database_fobs_code          2243832
_shelx_estimated_absorpt_t_min   0.842
_shelx_estimated_absorpt_t_max   0.975
_shelx_hkl_checksum              17703
_shelx_res_checksum              41291