Co-Crystals of Zwitterionic GABA API’s Pregabalin and Phenibut: Properties and Application
Komisarek, Daniel; Haj Hassani Sohi, Takin; Vasylyeva, Vera; CrystEngComm  (2022) –; doi:10.1039/D2CE01416E

data_7245858
_publ_section_title
;
 Co-Crystals of Zwitterionic GABA API&#x2019;s Pregabalin and Phenibut:
 Properties and Application
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE01416E
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H18 N O2, C4 H5 O5'
_chemical_formula_sum            'C12 H23 N O7'
_chemical_formula_weight         293.31
_chemical_name_common            '(S)-Pregabalin (R)-Malic Acid'
_chemical_name_systematic
'(S)-3-isobutyl-\^I^3^-aminobutyric acid (R)-2-Hydroxysuccinic acid'
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-05-03 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.44040(10)
_cell_length_b                   7.70390(10)
_cell_length_c                   25.9566(3)
_cell_measurement_reflns_used    18167
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.5860
_cell_measurement_theta_min      5.9410
_cell_volume                     1487.83(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.964
_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     36.00 102.00   0.50    0.10    --   49.27  55.00 137.00  132
  2  \w    104.00 129.00   0.50    0.20    --  109.41  19.00  90.00   50
  3  \w    152.00 178.00   0.50    0.20    --  109.41  19.00  90.00   52
  4  \w    101.00 141.00   0.50    0.20    --  109.41  71.00 -18.00   80
  5  \w     90.00 122.00   0.50    0.20    --  109.41  77.00 -30.00   64
  6  \w    125.00 168.00   0.50    0.20    --  109.41  38.00 -60.00   86
  7  \w    136.00 169.00   0.50    0.20    --  109.41  19.00-150.00   66
  8  \w    -93.00 -31.00   0.50    0.20    --  -90.00  71.00 -17.00  124
  9  \w    -49.00 -24.00   0.50    0.20    --  -90.00  54.00 -70.30   50
 10  \w    -48.00 -18.00   0.50    0.20    --  -90.00  57.00 -60.00   60
 11  \w    -48.00 -23.00   0.50    0.20    --  -90.00  38.00 -90.00   50
 12  \w    -48.00 -23.00   0.50    0.20    --  -90.00  38.00   0.00   50
 13  \w    -54.00 -21.00   0.50    0.20    --  -90.00  57.00  60.00   66
 14  \w    -68.00 -26.00   0.50    0.20    --  -90.00  55.00 137.00   84
 15  \w    -48.00 -23.00   0.50    0.20    --  -90.00  38.00  90.00   50
 16  \w    -48.00 -23.00   0.50    0.20    --  -90.00  38.00  30.00   50
 17  \w    -48.00 -23.00   0.50    0.20    --  -90.00  38.00-150.00   50
 18  \w    -61.00   1.00   0.50    0.10    --  -49.27 104.00-135.00  124
 19  \w   -117.00 -68.00   0.50    0.20    --  -90.00 -77.00-180.00   98
 20  \w    -95.00 -70.00   0.50    0.20    --  -90.00 -74.00-140.56   50
 21  \w   -136.00 -74.00   0.50    0.20    --  -90.00 -71.00-148.00  124
 22  \w    -94.00 -68.00   0.50    0.20    --  -90.00 -77.00 -60.00   52
 23  \w   -101.00 -73.00   0.50    0.20    --  -90.00 -66.00 -66.44   56
 24  \w   -105.00 -76.00   0.50    0.20    --  -90.00 -57.00 -30.00   58
 25  \w   -161.00-127.00   0.50    0.20    --  -90.00 -57.00 -90.00   68
 26  \w   -158.00-132.00   0.50    0.20    --  -90.00 -66.00 -66.44   52
 27  \w   -115.00 -90.00   0.50    0.20    --  -90.00 -57.00 -90.00   50
 28  \w   -158.00-112.00   0.50    0.20    --  -90.00 -57.00 -30.00   92
 29  \w   -146.00 -80.00   0.50    0.20    --  -90.00 -38.00 -90.00  132
 30  \w   -153.00 -77.00   0.50    0.20    --  -90.00 -55.00  -5.00  152
 31  \w   -122.00 -83.00   0.50    0.20    --  -90.00 -38.00  30.00   78
 32  \w   -110.00 -80.00   0.50    0.20    --  -90.00 -15.00  43.49   60
 33  \w   -162.00-115.00   0.50    0.20    --  -90.00 -15.00  43.49   94
 34  \w   -155.00 -70.00   0.50    0.20    --  -90.00 -73.00 165.36  170
 35  \w   -118.00 -75.00   0.50    0.20    --  -90.00 -61.00 179.29   86
 36  \w   -111.00 -86.00   0.50    0.20    --  -90.00 -99.00  90.00   50
 37  \w   -113.00 -84.00   0.50    0.20    --  -90.00-104.00 123.00   58
 38  \w   -148.00-122.00   0.50    0.20    --  -90.00-104.00 123.00   52
 39  \w   -121.00 -90.00   0.50    0.20    --  -90.00 -99.00 150.00   62
 40  \w   -111.00 -82.00   0.50    0.10    --  -49.27-125.00 -60.00   58
 41  \w   -102.00 -73.00   0.50    0.10    --  -49.27-125.00 -90.00   58
 42  \w   -160.00-130.00   0.50    0.20    --  -90.00 -99.00-180.00   60
 43  \w    -11.00  15.00   0.50    0.10    --   49.27 -19.00 -90.00   52
 44  \w    -10.00  17.00   0.50    0.10    --   49.27 -19.00-150.00   54
 45  \w     45.00  83.00   0.50    0.20    --  109.41 -71.00-148.00   76
 46  \w    -18.00  10.00   0.50    0.10    --   49.27 -19.00  30.00   56
 47  \w     51.00  98.00   0.50    0.20    --  109.41 -99.00 -60.00   94
 48  \w     66.00 100.00   0.50    0.20    --  109.41-124.00 -18.47   68
 49  \w     41.00  74.00   0.50    0.20    --  109.41-125.00  60.00   66
 50  \w     37.00  97.00   0.50    0.20    --  109.41-104.00 123.00  120
 51  \w     39.00  69.00   0.50    0.20    --  109.41 -99.00-180.00   60
 52  \w     81.00 107.00   0.50    0.20    --  109.41-103.00-171.03   52
 53  \w     76.00 105.00   0.50    0.20    --  109.41 -99.00-180.00   58
 54  \w     43.00  91.00   0.50    0.20    --  109.41 -99.00-150.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0187930000
_diffrn_orient_matrix_UB_12      -0.0547217000
_diffrn_orient_matrix_UB_13      0.0568311000
_diffrn_orient_matrix_UB_21      0.1634238000
_diffrn_orient_matrix_UB_22      -0.1212174000
_diffrn_orient_matrix_UB_23      -0.0058544000
_diffrn_orient_matrix_UB_31      0.1257511000
_diffrn_orient_matrix_UB_32      0.1493027000
_diffrn_orient_matrix_UB_33      0.0160996000
_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  0.0375
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            22743
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.790
_diffrn_reflns_theta_min         5.992
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.500
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.92a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate'
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1174 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0294P)^2^+0.6823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0778
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                2947
_reflns_number_total             3009
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01416e2.cif
_cod_data_source_block           S-Pregabalin_R-Malic_Acid
_cod_database_code               7245858
_chemical_oxdiff_formula         'C8 H17 N O2 C4 H5 O5'
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.735
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_res_checksum              62000
_shelx_hkl_checksum              16052
_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 1.237
_oxdiff_exptl_absorpt_empirical_full_min 0.823