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_2108681
_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_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                   29.0583(2)
_cell_length_b                   9.15479(8)
_cell_length_c                   4.70223(4)
_cell_measurement_reflns_used    31071
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.0870
_cell_measurement_theta_min      2.3280
_cell_volume                     1250.900(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_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      100(2)
_diffrn_detector_area_resol_mean 10.3457
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -49.00 103.00   0.50   12.50    --   -0.23  57.00 -30.00  304
  2  \w     23.00 112.00   0.50   25.00    --   43.04-125.00 -60.00  178
  3  \w     14.00  68.00   0.50   25.00    --   43.04  57.00-120.00  108
  4  \w    100.00 144.00   0.50   25.00    --   43.04  57.00-120.00   88
  5  \w    -30.00  -1.00   0.50   25.00    --   43.04 131.00  69.59   58
  6  \w      0.00  88.00   0.50   25.00    --   43.04  57.00 120.00  176
  7  \w    114.00 140.00   0.50   25.00    --   43.04  57.00 -90.00   52
  8  \w    110.00 144.00   0.50   25.00    --   43.04 125.00  90.00   68
  9  \w      7.00 148.00   0.50   25.00    --   43.04  77.00 150.00  282
 10  \w     -5.00  43.00   0.50   25.00    --   43.04  77.00 -60.00   96
 11  \w     49.00 126.00   0.50   25.00    --   43.04  77.00 -60.00  154
 12  \w     48.00  85.00   0.50   25.00    --   43.04  57.00 -90.00   74
 13  \w      0.00  83.00   0.50   25.00    --   43.04  77.00   0.00  166
 14  \w    122.00 148.00   0.50   25.00    --   43.04  77.00   0.00   52
 15  \w    100.00 138.00   0.50   25.00    --   43.04 125.00-180.00   76
 16  \w     15.00  41.00   0.50   25.00    --   43.04  57.00 -90.00   52
 17  \w    -82.00  59.00   0.50   25.00    --  -43.51  77.00-180.00  282
 18  \w      6.00  59.00   0.50   25.00    --  -43.51  19.00  60.00  106
 19  \w   -141.00 -33.00   0.50   25.00    --  -43.51  19.00  60.00  216
;
_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  0.0260
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            43507
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.218
_diffrn_reflns_theta_min         2.332
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.589
_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         0.478
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 2532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         6327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0276
_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^)+(0.0532P)^2^+0.0676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0778
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                6109
_reflns_number_total             6327
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            px5026sup1.cif
_cod_data_source_block           picasc_100
_cod_database_code               2108681
_cod_database_fobs_code          2108681
_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              69299
_shelx_hkl_checksum              15819
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;