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_7245857
_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 (S)-Malic Acid'
_chemical_name_systematic
'(S)-3-isobutyl-\^I^3^-aminobutyric acid (S)-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                   7.50090(10)
_cell_length_b                   7.55810(10)
_cell_length_c                   26.1805(3)
_cell_measurement_reflns_used    5790
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.2400
_cell_measurement_theta_min      3.3770
_cell_volume                     1484.24(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      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.909
_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    -71.00 -18.00   0.50    3.00    --  -90.00 124.00-146.00  106
  2  \w   -161.00-100.00   0.50    3.00    --  -90.00 -15.00-156.00  122
  3  \w     74.00 107.00   0.50    3.00    --  109.41-113.00  37.00   66
  4  \w     38.00  64.00   0.50    3.00    --  109.41-113.00  37.00   52
  5  \w    -26.00   7.00   0.50    1.00    --  -49.27  19.00 150.00   66
  6  \w   -122.00 -46.00   0.50    1.00    --  -49.27 -15.00-156.00  152
  7  \w    -22.00   7.00   0.50    1.00    --   49.27 -19.00 120.00   58
  8  \w     43.00  69.00   0.50    1.00    --   49.27-124.00 134.00   52
  9  \w    -47.00 -18.00   0.50    3.00    --  -90.00  38.00-150.00   58
 10  \w    -48.00 -22.00   0.50    3.00    --  -90.00  38.00 150.00   52
 11  \w    -48.00 -22.00   0.50    3.00    --  -90.00  38.00-120.00   52
 12  \w    -44.00 -19.00   0.50    3.00    --  -90.00 125.00  30.00   50
 13  \w    -48.00 -23.00   0.50    3.00    --  -90.00  38.00   0.00   50
 14  \w    -48.00 -23.00   0.50    3.00    --  -90.00  38.00  90.00   50
 15  \w    -83.00 -58.00   0.50    3.00    --  -90.00 125.00  30.00   50
 16  \w    -71.00 -29.00   0.50    3.00    --  -90.00  57.00 150.00   84
 17  \w   -159.00-133.00   0.50    3.00    --  -90.00 -99.00  30.00   52
 18  \w   -128.00-102.00   0.50    3.00    --  -90.00 -99.00  30.00   52
 19  \w     41.00  84.00   0.50    3.00    --  109.41-124.00 134.00   86
 20  \w     44.00  69.00   0.50    3.00    --  109.41 -77.00 120.00   50
 21  \w     49.00  97.00   0.50    3.00    --  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      -0.0133294000
_diffrn_orient_matrix_UB_12      -0.0242566000
_diffrn_orient_matrix_UB_13      0.0583121000
_diffrn_orient_matrix_UB_21      0.0390636000
_diffrn_orient_matrix_UB_22      -0.1990099000
_diffrn_orient_matrix_UB_23      -0.0061619000
_diffrn_orient_matrix_UB_31      0.2010989000
_diffrn_orient_matrix_UB_32      0.0370244000
_diffrn_orient_matrix_UB_33      0.0050949000
_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  0.0218
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8059
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.728
_diffrn_reflns_theta_min         3.376
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.915
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.535
_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    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1070 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0249
_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^)+(0.0277P)^2^+0.3039P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0594
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.860
_reflns_number_gt                2713
_reflns_number_total             2826
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01416e2.cif
_cod_data_source_block           S-PGB_S_Malic_acid
_cod_database_code               7245857
_chemical_oxdiff_formula         'C8 H18 N O2 C4 H5 O5'
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.797
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_res_checksum              15242
_shelx_hkl_checksum              36750
_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 1.344
_oxdiff_exptl_absorpt_empirical_full_min 0.640