The curious case of proton migration under pressure in the malonic acid and 4,4'-bipyridine cocrystal.
Patyk-Kaźmierczak, Ewa; Izquierdo-Ruiz, Fernando; Lobato, Alvaro; Kaźmierczak, Michał; Moszczyńska, Ida; Olejniczak, Anna; Recio, J. Manuel; IUCrJ 11 (2024) 168–181; doi:10.1107/S2052252524000344

data_1571127
_publ_section_title
;
 The curious case of proton migration under pressure in the malonic acid
 and 4,4'-bipyridine cocrystal.
;
_journal_coeditor_code           YC5045
_journal_issue                   2
_journal_name_full               IUCrJ
_journal_page_first              168
_journal_page_last               181
_journal_paper_doi               10.1107/S2052252524000344
_journal_volume                  11
_journal_year                    2024
_chemical_formula_moiety         'C3 H4 O4, C10 H8 N2'
_chemical_formula_sum            'C13 H12 N2 O4'
_chemical_formula_weight         260.251
_chemical_name_systematic        'Malonic acid 4,4'-bipyridyl'
_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_Int_Tables_number      15
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-14
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.783(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.5688(9)
_cell_length_b                   4.0772(3)
_cell_length_c                   15.9523(8)
_cell_measurement_reflns_used    2314
_cell_measurement_temperature    298
_cell_measurement_theta_max      75.6400
_cell_measurement_theta_min      4.6510
_cell_volume                     1230.64(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5384
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9721
_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   -114.00 -13.00   1.00    1.50    --  -41.23 -57.00-150.00  101
  2  \w    -88.00   7.00   1.00    1.50    --  -41.23 110.00  99.00   95
  3  \w    -66.00  32.00   1.00    1.50    --  -41.23  57.00   0.00   98
  4  \w     59.00 158.00   1.00    1.50    --  112.00  15.00 150.00   99
  5  \w     86.00 158.00   1.00    1.50    --  112.00  45.00-150.00   72
  6  \w     36.00 106.00   1.00    1.50    --  112.00 -77.00  60.00   70
  7  \w     84.00 158.00   1.00    1.50    --  112.00  30.00   0.00   74
  8  \w     40.00  71.00   1.00    1.50    --  112.00 -61.00   0.00   31
  9  \w     29.00 107.00   1.00    1.50    --  112.00 -94.00 150.00   78
 10  \w     40.00  71.00   1.00    1.50    --  112.00 -61.00 -30.00   31
 11  \w     40.00  71.00   1.00    1.50    --  112.00 -61.00  30.00   31
 12  \w     24.00 158.00   1.00    1.50    --  112.00   0.00 -30.00  134
 13  \w     40.00  71.00   1.00    1.50    --  112.00 -61.00-180.00   31
 14  \w   -114.00 -13.00   1.00    1.50    --  -41.23 -57.00 -60.00  101
 15  \w     13.00 114.00   1.00    1.50    --   41.23  57.00 150.00  101
 16  \w     13.00 114.00   1.00    1.50    --   41.23  57.00  60.00  101
 17  \w     40.00  71.00   1.00    1.50    --  112.00 -61.00-120.00   31
 18  \w     82.00 158.00   1.00    1.50    --  112.00  77.00  30.00   76
 19  \w     83.00 158.00   1.00    1.50    --  112.00  61.00 150.00   75
 20  \w     36.00 109.00   1.00    1.50    --  112.00-111.00   0.00   73
 21  \w     40.00  71.00   1.00    1.50    --  112.00 -61.00 150.00   31
 22  \w     40.00  71.00   1.00    1.50    --  112.00 -61.00 -90.00   31
 23  \w    -42.00  33.00   1.00    1.50    --  -41.23  37.00 -60.00   75
 24  \w    -42.00  33.00   1.00    1.50    --  -41.23  37.00-120.00   75
 25  \w    -39.00  26.00   1.00    1.50    --   41.23 -19.00  30.00   65
 26  \w     83.00 158.00   1.00    1.50    --  112.00  61.00   0.00   75
 27  \w     83.00 158.00   1.00    1.50    --  112.00  61.00 -90.00   75
 28  \w     40.00  71.00   1.00    1.50    --  112.00 -61.00 120.00   31
 29  \w     86.00 115.00   1.00    1.50    --  112.00  45.00-120.00   29
 30  \w     40.00  71.00   1.00    1.50    --  112.00 -61.00-150.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0490070000
_diffrn_orient_matrix_UB_12      0.0130253000
_diffrn_orient_matrix_UB_13      -0.0924130000
_diffrn_orient_matrix_UB_21      -0.0629438000
_diffrn_orient_matrix_UB_22      0.0854566000
_diffrn_orient_matrix_UB_23      0.0375269000
_diffrn_orient_matrix_UB_31      0.0163499000
_diffrn_orient_matrix_UB_32      0.3677648000
_diffrn_orient_matrix_UB_33      -0.0054666000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9721
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6263
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9721
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         76.22
_diffrn_reflns_theta_min         4.67
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       plate
_exptl_crystal_F_000             546.098
_exptl_crystal_size_max          0.229
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.2324
_refine_diff_density_min         -0.2758
_refine_diff_density_rms         0.0594
_refine_ls_d_res_high            0.7938
_refine_ls_d_res_low             9.4605
_refine_ls_goodness_of_fit_ref   1.0846
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0846
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0336P)^2^+0.8691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              -24
_reflns_limit_k_max              4
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                834
_reflns_number_total             1256
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            yc5045.cif
_cod_data_source_block           BIPYMA
_cod_database_code               1571127
_chemical_oxdiff_formula         'C13 H12 O4 N2'
_olex2_refinement_description
;
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.444
_oxdiff_exptl_absorpt_empirical_full_min 0.805