Crystal structure of zymonic acid and a redetermination of its precursor, pyruvic acid
Heger, Dominik; Eugene, Alexis J.; Parkin, Sean R.; Guzman, Marcelo I.; Acta Crystallographica Section E 75 (2019) 858–862; doi:10.1107/S2056989019007072

data_2242955
_publ_section_title
;
 Crystal structure of zymonic acid and a redetermination of its precursor,
 pyruvic acid
;
_journal_coeditor_code           HB7818
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              858
_journal_page_last               862
_journal_paper_doi               10.1107/S2056989019007072
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C6 H6 O5'
_chemical_formula_moiety         'C6 H6 O5'
_chemical_formula_sum            'C6 H6 O5'
_chemical_formula_weight         158.11
_chemical_name_common
;
Zymonic acid
;
_chemical_name_systematic
;
4-Hydroxy-2-methyl-5-oxo-2,5-dihydrofuran-2-carboxylic acid
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 95.169(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.145(3)
_cell_length_b                   6.6523(7)
_cell_length_c                   8.6201(7)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.18
_cell_volume                     1378.9(3)
_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 in SHELXTL</i> (Sheldrick, 2008)
;
_computing_publication_material
;
<i>SHELXL</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 5.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18595
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         3.177
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.721
_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    1.523
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.239
_refine_ls_extinction_coef       0.0057(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015a)
;
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0428P)^2^+1.4377P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                1392
_reflns_number_total             1586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7818sup1.cif
_cod_data_source_block           zymonic
_cod_database_code               2242955
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.997
_shelx_hkl_checksum              3947
_shelx_res_checksum              12745
_cod_database_fobs_code 2242955