Tautomeric polymorphism of the neuroactive inhibitor kynurenic acid
Pogoda, Dorota; Janczak, Jan; Pawlak, Sylwia; Zaworotko, Michael; Videnova-Adrabinska, Veneta; Acta Crystallographica Section C 75 (2019) 793–805; doi:10.1107/S2053229619005990

data_2021697
_publ_section_title
;
 Tautomeric polymorphism of the neuroactive inhibitor kynurenic acid
;
_journal_coeditor_code           UK3175
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              793
_journal_page_last               805
_journal_paper_doi               10.1107/S2053229619005990
_journal_volume                  75
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_iupac          'C10 H7 N O3, C2 H6 O S'
_chemical_formula_moiety         'C10 H7 N O3, C2 H6 O S'
_chemical_formula_sum            'C12 H13 N O4 S'
_chemical_formula_weight         267.29
_chemical_name_common
;
Kynurenic acid  dimethyl sulfoxide monosolvate
;
_chemical_name_systematic
;
4-Hydroxyquinoline-2-carboxylic acid dimethyl sulfoxide monosolvate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9552(3)
_cell_length_b                   10.8444(6)
_cell_length_c                   22.7982(11)
_cell_measurement_reflns_used    4335
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.6480
_cell_measurement_theta_min      4.0170
_cell_volume                     1225.09(12)
_computing_cell_refinement
;
CrysAlis RED (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis CCD (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis RED (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2005)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.6249
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Kuma KM-4 with CCD detector'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14513
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         29.534
_diffrn_reflns_theta_min         2.592
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.253
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 999 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.11(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0461P)^2^+0.2943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0849
_reflns_number_gt                2756
_reflns_number_total             3044
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            uk3175sup1.cif
_cod_data_source_block           kyn_100
_cod_database_code               2021697
_cod_database_fobs_code          2021697
_shelx_estimated_absorpt_t_min   0.897
_shelx_estimated_absorpt_t_max   0.968
_shelx_hkl_checksum              80286
_shelx_res_checksum              6156