A cocrystal of <small>L</small>-ascorbic acid with picolinic acid: the role of O—H···O, N—H···O and C—H···O hydrogen bonds and <small>L</small>-ascorbic acid conformation in structure stabilization
Evtushenko, Diana N.; Arkhipov, Sergey G.; Fateev, Alexander V.; Izaak, Tatyana I.; Egorova, Lidia A.; Skorik, Nina A.; Vodyankina, Olga V.; Boldyreva, Elena V.; Acta Crystallographica Section B 76 (2020) –; doi:10.1107/S2052520620012421

data_2108680
_publ_section_title
;
 A cocrystal of <small>L</small>-ascorbic acid with picolinic acid: the
 role of O---H&#x00B7;&#x00B7;&#x00B7;O, N---H&#x00B7;&#x00B7;&#x00B7;O
 and C---H&#x00B7;&#x00B7;&#x00B7;O hydrogen bonds and
 <small>L</small>-ascorbic acid conformation in structure stabilization
;
_journal_coeditor_code           PX5026
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520620012421
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C6 H8 O6, C6 H5 N O2'
_chemical_formula_sum            'C12 H13 N O8'
_chemical_formula_weight         299.23
_chemical_melting_point          455.6
_chemical_name_systematic        'L-ascorbic acid picolinic acid cocrystal'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.1612(4)
_cell_length_b                   9.20700(10)
_cell_length_c                   4.73870(10)
_cell_measurement_reflns_used    13377
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.4730
_cell_measurement_theta_min      2.0830
_cell_volume                     1272.28(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3457
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
  1 omega    5.00   76.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       31.1406  -99.0000  -30.0000 142

  2 omega    6.00   73.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       31.1406  -99.0000 -150.0000 134

  3 omega   57.00  125.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       31.1406    0.0000 -180.0000 136

  4 omega  -62.00   16.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       31.1406    0.0000 -180.0000 156

  5 omega   97.00  133.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       31.1406  145.0000 -137.0000 72

  6 omega -140.00   14.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.7656  -77.0000 -120.0000 308

  7 omega  -47.00   63.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.7656   37.0000  120.0000 220

  8 omega -136.00   14.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.7656  -77.0000    0.0000 300

  9 omega -140.00  -56.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.7656  -77.0000  120.0000 168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            23240
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.931
_diffrn_reflns_theta_min         2.320
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.4496
_exptl_crystal_size_mid          0.3366
_exptl_crystal_size_min          0.2778
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1551 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0502P)^2^+0.1136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0863
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                3979
_reflns_number_total             4223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            px5026sup1.cif
_cod_data_source_block           picasc_293
_cod_database_code               2108680
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H,H,H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H,H) groups
;
_shelx_res_checksum              14922
_shelx_hkl_checksum              1871
_olex2_submission_special_instructions 'No special instructions were received'
_cod_database_fobs_code 2108680