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_7245862
_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 O3'
_chemical_formula_sum            'C16 H25 N O5'
_chemical_formula_weight         311.37
_chemical_name_common            '(S)-Pregabalin (R)-Mandelic Acid'
_chemical_name_systematic
'(S)-3-isobutyl-\^I^3^-aminobutyric acid (R)-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_date             2021-09-08
_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                 92.6620(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.07710(10)
_cell_length_b                   29.9265(5)
_cell_length_c                   9.30660(10)
_cell_measurement_reflns_used    14723
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      77.6270
_cell_measurement_theta_min      2.9660
_cell_volume                     1690.73(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.90a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.90a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.90a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_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    100.00 167.00   0.50    0.08    --  109.41  19.00 150.00  134
  2  \w    144.00 178.00   0.50    0.08    --  109.41  38.00   0.00   68
  3  \w    100.00 126.00   0.50    0.08    --  109.41  38.00   0.00   52
  4  \w    -48.00 -20.00   0.50    0.08    --  -90.00  38.00-150.00   56
  5  \w    -67.00 -32.00   0.50    0.08    --  -90.00  57.00-180.00   70
  6  \w    -47.00 -19.00   0.50    0.08    --  -90.00  38.00-120.00   56
  7  \w    -47.00 -18.00   0.50    0.08    --  -90.00  38.00 -90.00   58
  8  \w    -65.00 -40.00   0.50    0.08    --  -90.00  57.00 -30.00   50
  9  \w    -45.00 -20.00   0.50    0.08    --  -90.00  38.00 -30.00   50
 10  \w    -47.00 -20.00   0.50    0.08    --  -90.00  38.00  30.00   54
 11  \w    -46.00 -19.00   0.50    0.08    --  -90.00  38.00  90.00   54
 12  \w    -47.00 -22.00   0.50    0.08    --  -90.00  38.00 150.00   50
 13  \w    -31.00  24.00   0.50    0.05    --  -49.27  19.00 150.00  110
 14  \w    -26.00  19.00   0.50    0.05    --  -49.27  19.00-120.00   90
 15  \w    106.00 131.00   0.50    0.08    --  109.41 147.00-155.00   50
 16  \w    107.00 162.00   0.50    0.08    --  109.41 125.00 -30.00  110
 17  \w    112.00 137.00   0.50    0.08    --  109.41 125.00  39.00   50
 18  \w    -23.00  20.00   0.50    0.05    --   49.27 -19.00 -60.00   86
 19  \w     38.00  87.00   0.50    0.08    --  109.41 -77.00 -30.00   98
 20  \w     38.00  99.00   0.50    0.08    --  109.41 -77.00  30.00  122
 21  \w     51.00  91.00   0.50    0.08    --  109.41 -77.00  90.00   80
 22  \w     37.00  87.00   0.50    0.08    --  109.41 -99.00 150.00  100
 23  \w     96.00 124.00   0.50    0.08    --  109.41-147.00 155.00   56
 24  \w     75.00 104.00   0.50    0.05    --   49.27-147.00 155.00   58
 25  \w     81.00 109.00   0.50    0.08    --  109.41-125.00  60.00   56
 26  \w     50.00  76.00   0.50    0.08    --  109.41-125.00  60.00   52
 27  \w     43.00 101.00   0.50    0.08    --  109.41-125.00   0.00  116
 28  \w     72.00 110.00   0.50    0.08    --  109.41-125.00 -38.00   76
 29  \w     63.00 107.00   0.50    0.08    --  109.41-107.00 -65.01   88
 30  \w     49.00 109.00   0.50    0.08    --  109.41-125.00 -90.00  120
 31  \w     63.00 107.00   0.50    0.08    --  109.41-107.00-161.82   88
 32  \w     36.00  69.00   0.50    0.05    --   49.27-125.00 -38.00   66
 33  \w    -68.00 -40.00   0.50    0.05    --  -49.27 125.00  39.00   56
 34  \w    -87.00 -62.00   0.50    0.05    --  -49.27 147.00-155.00   50
 35  \w    -94.00 -62.00   0.50    0.08    --  -90.00 147.00-155.00   64
 36  \w    -85.00 -19.00   0.50    0.08    --  -90.00 125.00  39.00  132
 37  \w   -161.00 -82.00   0.50    0.08    --  -90.00 -38.00 150.00  158
 38  \w   -120.00 -32.00   0.50    0.05    --  -49.27 -77.00 -90.00  176
 39  \w   -120.00 -74.00   0.50    0.05    --  -49.27-125.00 -38.00   92
 40  \w   -118.00 -74.00   0.50    0.05    --  -49.27-125.00  60.00   88
 41  \w   -120.00 -73.00   0.50    0.05    --  -49.27-125.00 120.00   94
 42  \w    -95.00 -69.00   0.50    0.05    --  -49.27-147.00 155.00   52
 43  \w   -114.00 -68.00   0.50    0.08    --  -90.00-147.00 155.00   92
 44  \w   -124.00 -86.00   0.50    0.08    --  -90.00 -99.00  90.00   76
 45  \w   -105.00 -74.00   0.50    0.08    --  -90.00-125.00 -38.00   62
;
_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      0.0167058000
_diffrn_orient_matrix_UB_12      -0.0513094000
_diffrn_orient_matrix_UB_13      -0.0064926000
_diffrn_orient_matrix_UB_21      -0.1496025000
_diffrn_orient_matrix_UB_22      -0.0002554000
_diffrn_orient_matrix_UB_23      -0.1382771000
_diffrn_orient_matrix_UB_31      0.2042864000
_diffrn_orient_matrix_UB_32      0.0040486000
_diffrn_orient_matrix_UB_33      -0.0911692000
_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  0.0874
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_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            21324
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.829
_diffrn_reflns_theta_min         2.953
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.351
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.90a (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    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 2899 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         6745
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0808P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.905
_reflns_number_gt                6480
_reflns_number_total             6745
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01416e2.cif
_cod_data_source_block           S-PGB_R-MAN
_cod_database_code               7245862
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C8 H18 N O2 C8 H7 O3'
_shelx_estimated_absorpt_t_max   0.896
_shelx_estimated_absorpt_t_min   0.689
_olex2_refinement_description
;
;
_shelx_res_checksum              10716
_shelx_hkl_checksum              73846
_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 1.748
_oxdiff_exptl_absorpt_empirical_full_min 0.752