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_7245863
_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 H17 N O2, C8 H8 O3'
_chemical_formula_sum            'C16 H25 N O5'
_chemical_formula_weight         311.37
_chemical_name_common            '(S)-Pregabalin (S)-Mandelic Acid'
_chemical_name_systematic
'(S)-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_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                 90.462(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.24550(10)
_cell_length_b                   27.3880(5)
_cell_length_c                   9.9624(2)
_cell_measurement_reflns_used    11933
_cell_measurement_temperature    99.98(13)
_cell_measurement_theta_max      76.8230
_cell_measurement_theta_min      3.1950
_cell_volume                     1704.03(5)
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.951
_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    -24.00   5.00   0.50    0.05    --   49.26 -19.00  30.00   58
  2  \w     10.00  60.00   0.50    0.05    --   49.26 -57.00-120.00  100
  3  \w    112.00 138.00   0.50    0.19    --  109.41 108.00 128.00   52
  4  \w     49.00  89.00   0.50    0.19    --  109.41 -77.00  90.00   80
  5  \w     81.00 106.00   0.50    0.19    --  109.41 -99.00 150.00   50
  6  \w     38.00  76.00   0.50    0.19    --  109.41-125.00  90.00   76
  7  \w     45.00 106.00   0.50    0.19    --  109.41-125.00 -30.00  122
  8  \w     78.00 109.00   0.50    0.19    --  109.41-125.00 -90.00   62
  9  \w     70.00 112.00   0.50    0.19    --  109.41-125.00-120.00   84
 10  \w     39.00  68.00   0.50    0.19    --  109.41-125.00-120.00   58
 11  \w     45.00  70.00   0.50    0.19    --  109.41-125.00 -90.00   50
 12  \w     45.00 109.00   0.50    0.19    --  109.41-125.00   0.00  128
 13  \w     82.00 112.00   0.50    0.19    --  109.41-125.00  90.00   60
 14  \w     30.00  55.00   0.50    0.05    --   49.26-108.00  31.00   50
 15  \w     57.00  83.00   0.50    0.19    --  109.41-108.00  31.00   52
 16  \w     41.00  95.00   0.50    0.19    --  109.41 -99.00  30.00  108
 17  \w     81.00 108.00   0.50    0.19    --  109.41-111.00 100.70   54
 18  \w     38.00  78.00   0.50    0.19    --  109.41-111.00 100.70   80
 19  \w    -59.00 -19.00   0.50    0.19    --  -90.00 125.00  60.00   80
 20  \w    -81.00 -36.00   0.50    0.19    --  -90.00 108.00 128.00   90
 21  \w    -82.00  -8.00   0.50    0.05    --  -49.26 108.00 128.00  148
 22  \w    -50.00 -23.00   0.50    0.19    --  -90.00 125.00 -30.00   54
 23  \w   -108.00 -76.00   0.50    0.19    --  -90.00  77.00 -30.00   64
 24  \w    -46.00 -19.00   0.50    0.19    --  -90.00  77.00 -30.00   54
 25  \w    -48.00 -22.00   0.50    0.19    --  -90.00  38.00 -90.00   52
 26  \w    -48.00 -18.00   0.50    0.19    --  -90.00  38.00-120.00   60
 27  \w    -47.00 -19.00   0.50    0.19    --  -90.00  38.00-180.00   56
 28  \w    -48.00 -19.00   0.50    0.19    --  -90.00  38.00-150.00   58
 29  \w    -48.00 -20.00   0.50    0.19    --  -90.00  38.00 -60.00   56
 30  \w    -48.00 -18.00   0.50    0.19    --  -90.00  38.00 -30.00   60
 31  \w    -47.00 -22.00   0.50    0.19    --  -90.00  38.00   0.00   50
 32  \w    -47.00 -19.00   0.50    0.19    --  -90.00  38.00 150.00   56
 33  \w    -31.00  24.00   0.50    0.05    --  -49.26  19.00  60.00  110
 34  \w   -116.00 -41.00   0.50    0.05    --  -49.26 -57.00 -30.00  150
 35  \w   -120.00 -81.00   0.50    0.05    --  -49.26-125.00  60.00   78
 36  \w   -159.00 -76.00   0.50    0.19    --  -90.00 -57.00 -60.00  166
 37  \w   -120.00 -95.00   0.50    0.05    --  -49.26-125.00-150.00   50
 38  \w   -120.00 -73.00   0.50    0.05    --  -49.26-125.00-180.00   94
 39  \w   -145.00-120.00   0.50    0.19    --  -90.00 -99.00 -60.00   50
 40  \w   -161.00-135.00   0.50    0.19    --  -90.00 -99.00-120.00   52
 41  \w   -128.00 -88.00   0.50    0.19    --  -90.00 -99.00-120.00   80
 42  \w   -111.00 -86.00   0.50    0.19    --  -90.00 -99.00 -60.00   50
 43  \w   -131.00 -86.00   0.50    0.19    --  -90.00-108.00  31.00   90
;
_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      0.0552045000
_diffrn_orient_matrix_UB_12      -0.0540630000
_diffrn_orient_matrix_UB_13      0.0252752000
_diffrn_orient_matrix_UB_21      -0.0653793000
_diffrn_orient_matrix_UB_22      0.0055818000
_diffrn_orient_matrix_UB_23      0.1480249000
_diffrn_orient_matrix_UB_31      -0.2312838000
_diffrn_orient_matrix_UB_32      -0.0145069000
_diffrn_orient_matrix_UB_33      -0.0370782000
_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  0.0597
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19149
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.793
_diffrn_reflns_theta_min         3.227
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.560
_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            Colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 2629 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         6561
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0583P)^2^+0.4320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.856
_reflns_number_gt                6135
_reflns_number_total             6561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01416e2.cif
_cod_data_source_block           S-PGB_S-Mandelic_Acid
_cod_database_code               7245863
_chemical_oxdiff_formula         'C8 H17 N O2 C8 H8 O3'
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.670
_olex2_refinement_description
;
;
_shelx_res_checksum              50900
_shelx_hkl_checksum              12156
_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 1.488
_oxdiff_exptl_absorpt_empirical_full_min 0.777