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_7245861
_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, C8 H7 N O2'
_chemical_formula_sum            'C16 H25 N O5'
_chemical_formula_weight         311.37
_chemical_name_common            '(R)-Pregabalin (S)-Mandelic Acid'
_chemical_name_systematic
'(R)-3-isobutyl-\^I^3^-aminobutyric acid (S)-2-Hydroxy-2-phenylacetic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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                 92.6410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.05170(10)
_cell_length_b                   29.8989(5)
_cell_length_c                   9.30690(10)
_cell_measurement_reflns_used    17743
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7720
_cell_measurement_theta_min      2.9390
_cell_volume                     1682.19(4)
_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 0.998
_diffrn_measured_fraction_theta_max 0.917
_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    -60.00 -22.00   0.50    0.17    --  -90.00  57.00  30.00   76
  2  \w    -61.00 -35.00   0.50    0.17    --  -90.00  57.00 -30.00   52
  3  \w     53.00  86.00   0.50    0.05    --   49.27  38.00 -30.00   66
  4  \w     99.00 135.00   0.50    0.17    --  109.41  29.00-110.00   72
  5  \w     76.00 106.00   0.50    0.05    --   49.27  29.00-110.00   60
  6  \w    -62.00 -36.00   0.50    0.17    --  -90.00  57.00  60.00   52
  7  \w    -69.00 -19.00   0.50    0.17    --  -90.00  57.00   0.00  100
  8  \w    -48.00 -19.00   0.50    0.17    --  -90.00  38.00 -30.00   58
  9  \w    -71.00 -46.00   0.50    0.17    --  -90.00  57.00 -90.00   50
 10  \w    -43.00 -18.00   0.50    0.17    --  -90.00  38.00 -90.00   50
 11  \w    -48.00 -19.00   0.50    0.17    --  -90.00  38.00-180.00   58
 12  \w    -75.00 -21.00   0.50    0.17    --  -90.00 125.00 -30.00  108
 13  \w    -80.00 -36.00   0.50    0.17    --  -90.00 125.00 150.00   88
 14  \w    -75.00 -38.00   0.50    0.05    --  -49.27 -19.00 -30.00   74
 15  \w   -119.00 -28.00   0.50    0.05    --  -49.27 -77.00 -30.00  182
 16  \w    -86.00 -29.00   0.50    0.05    --  -49.27 -77.00  30.00  114
 17  \w   -104.00 -79.00   0.50    0.05    --  -49.27 -29.00  88.00   50
 18  \w   -124.00 -72.00   0.50    0.17    --  -90.00 -77.00  60.00  104
 19  \w    -97.00 -72.00   0.50    0.17    --  -90.00 -75.00  26.07   50
 20  \w    -94.00 -68.00   0.50    0.17    --  -90.00 -77.00  30.00   52
 21  \w    -94.00 -69.00   0.50    0.17    --  -90.00 -77.00   0.00   50
 22  \w    -95.00 -70.00   0.50    0.17    --  -90.00 -77.00 -30.00   50
 23  \w    -97.00 -71.00   0.50    0.17    --  -90.00 -72.00 -43.62   52
 24  \w   -122.00 -69.00   0.50    0.17    --  -90.00 -75.00 -13.02  106
 25  \w   -143.00-117.00   0.50    0.17    --  -90.00 -72.00 -43.62   52
 26  \w   -161.00-104.00   0.50    0.17    --  -90.00 -72.00 -76.74  114
 27  \w    -97.00 -72.00   0.50    0.17    --  -90.00 -71.00  -1.58   50
 28  \w   -115.00 -71.00   0.50    0.17    --  -90.00 -71.00  13.02   88
 29  \w   -160.00-127.00   0.50    0.17    --  -90.00 -75.00  26.07   66
 30  \w   -156.00-113.00   0.50    0.17    --  -90.00 -74.00  46.81   86
 31  \w    -94.00 -69.00   0.50    0.17    --  -90.00 -74.00  44.12   50
 32  \w   -114.00 -73.00   0.50    0.17    --  -90.00 -66.00  22.34   82
 33  \w   -118.00 -73.00   0.50    0.17    --  -90.00 -66.00  -7.31   90
 34  \w    -96.00 -71.00   0.50    0.17    --  -90.00 -69.00   5.01   50
 35  \w    -98.00 -73.00   0.50    0.17    --  -90.00 -64.00  -5.51   50
 36  \w    -96.00 -71.00   0.50    0.17    --  -90.00 -71.00 -36.09   50
 37  \w    -98.00 -73.00   0.50    0.17    --  -90.00 -65.00 -58.30   50
 38  \w    -99.00 -74.00   0.50    0.17    --  -90.00 -64.00 -65.61   50
 39  \w   -161.00 -75.00   0.50    0.17    --  -90.00 -68.00 -65.17  172
 40  \w   -161.00-135.00   0.50    0.17    --  -90.00 -64.00  -5.51   52
 41  \w   -121.00 -90.00   0.50    0.17    --  -90.00 -29.00  88.00   62
 42  \w   -155.00-115.00   0.50    0.17    --  -90.00 -63.00 -39.71   80
 43  \w   -110.00 -74.00   0.50    0.17    --  -90.00 -63.00 -39.71   72
 44  \w   -128.00 -81.00   0.50    0.17    --  -90.00 -38.00-180.00   94
 45  \w   -158.00-133.00   0.50    0.17    --  -90.00 -38.00-180.00   50
 46  \w   -116.00 -77.00   0.50    0.05    --  -49.27-125.00-150.00   78
 47  \w    -24.00   2.00   0.50    0.05    --   49.27 -19.00 -60.00   52
 48  \w    -18.00  18.00   0.50    0.05    --   49.27 -19.00 -30.00   72
 49  \w     74.00  99.00   0.50    0.17    --  109.41 -77.00 -60.00   50
 50  \w     39.00  89.00   0.50    0.17    --  109.41 -77.00  90.00  100
 51  \w     -9.00  24.00   0.50    0.05    --   49.27 -29.00  88.00   66
 52  \w     70.00 102.00   0.50    0.17    --  109.41 -99.00 -60.00   64
 53  \w     43.00 101.00   0.50    0.17    --  109.41-125.00  90.00  116
 54  \w    -38.00  22.00   0.50    0.05    --  -49.27  29.00-110.00  120
;
_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      -0.2070703000
_diffrn_orient_matrix_UB_12      0.0190762000
_diffrn_orient_matrix_UB_13      0.0682755000
_diffrn_orient_matrix_UB_21      0.1164700000
_diffrn_orient_matrix_UB_22      -0.0037598000
_diffrn_orient_matrix_UB_23      0.1502268000
_diffrn_orient_matrix_UB_31      0.0923052000
_diffrn_orient_matrix_UB_32      0.0477024000
_diffrn_orient_matrix_UB_33      -0.0153049000
_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  0.0430
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            25468
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.135
_diffrn_reflns_theta_min         2.956
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.580
_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    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2806 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.15(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         6336
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0300
_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^)+(0.0358P)^2^+0.2370P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0733
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.853
_reflns_number_gt                6172
_reflns_number_total             6336
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01416e2.cif
_cod_data_source_block           R-PGB_S-MAN
_cod_database_code               7245861
_chemical_oxdiff_formula         'C8H18NO2 C8H7O3'
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.801
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_res_checksum              13169
_shelx_hkl_checksum              5345
_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 1.487
_oxdiff_exptl_absorpt_empirical_full_min 0.786