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_7245860
_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         'C10 H13 N O2, C8 H8 O3'
_chemical_formula_sum            'C18 H21 N O5'
_chemical_formula_weight         331.36
_chemical_name_common            '(R)-Phenibut (S)-Mandelic Acid'
_chemical_name_systematic
'(R)-3-phenyl-\^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                 95.469(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.1307(2)
_cell_length_b                   6.35390(10)
_cell_length_c                   13.0633(2)
_cell_measurement_reflns_used    12151
_cell_measurement_temperature    99.96(11)
_cell_measurement_theta_max      76.5310
_cell_measurement_theta_min      3.3430
_cell_volume                     837.05(2)
_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      99.96(11)
_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 0.941
_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     26.00  56.00   0.50    0.11    --   47.52  77.00 -30.00   60
  2  \w     41.00  67.00   0.50    0.11    --   62.00  76.00-130.76   52
  3  \w     42.00  69.00   0.50    0.11    --   62.00  73.00  82.12   54
  4  \w     44.00  70.00   0.50    0.11    --   62.00  70.00  71.08   52
  5  \w     38.00  87.00   0.50    0.11    --   58.00  72.00 121.00   98
  6  \w     51.00  78.00   0.50    0.11    --   47.52  19.00 120.00   54
  7  \w     81.00 107.00   0.50    0.44    --  110.04-113.00 -54.00   52
  8  \w     41.00 104.00   0.50    0.44    --  110.04 -99.00 -30.00  126
  9  \w     41.00  79.00   0.50    0.44    --  110.04-113.00 -54.00   76
 10  \w     39.00  65.00   0.50    0.44    --  110.04 -99.00  30.00   52
 11  \w     74.00 100.00   0.50    0.44    --  110.04 -99.00  30.00   52
 12  \w     70.00 106.00   0.50    0.44    --  110.04 -99.00  90.00   72
 13  \w     40.00  90.00   0.50    0.44    --  110.04 -99.00 150.00  100
 14  \w     40.00  66.00   0.50    0.44    --  110.04 -99.00  90.00   52
 15  \w     48.00 106.00   0.50    0.44    --  110.04 -99.00-120.00  116
 16  \w     42.00 106.00   0.50    0.44    --  110.04 -99.00-180.00  128
 17  \w     63.00  90.00   0.50    0.44    --  110.04 -99.00   0.00   54
 18  \w     39.00  99.00   0.50    0.44    --  110.04 -77.00  30.00  120
 19  \w     63.00 119.00   0.50    0.11    --   47.52-178.00  90.00  112
 20  \w     42.00  83.00   0.50    0.11    --   47.52-113.00 -54.00   82
 21  \w    108.00 141.00   0.50    0.44    --  110.04 113.00  37.00   66
 22  \w    -61.00 -18.00   0.50    0.44    --  -90.00 125.00  60.00   86
 23  \w    -74.00 -49.00   0.50    0.44    --  -90.00 113.00  37.00   50
 24  \w    -48.00  -7.00   0.50    0.11    --  -47.52 113.00  37.00   82
 25  \w    -68.00 -21.00   0.50    0.44    --  -90.00  57.00   0.00   94
 26  \w    -53.00 -19.00   0.50    0.44    --  -90.00  57.00 -90.00   68
 27  \w    -68.00 -37.00   0.50    0.44    --  -90.00  57.00-120.00   62
 28  \w    -45.00 -18.00   0.50    0.44    --  -90.00  38.00-120.00   54
 29  \w   -156.00-111.00   0.50    0.44    --  -90.00 -52.00 -14.84   90
 30  \w   -129.00-102.00   0.50    0.11    --  -58.00 -77.00 -96.31   54
 31  \w    -93.00 -48.00   0.50    0.44    --  -70.00 -77.00 -84.35   90
 32  \w    -64.00 -37.00   0.50    0.11    --  -58.00 -77.00 -96.31   54
 33  \w   -107.00 -69.00   0.50    0.44    --  -90.00 -77.00-180.00   76
 34  \w   -111.00 -69.00   0.50    0.44    --  -90.00 -77.00-150.00   84
 35  \w   -152.00-121.00   0.50    0.44    --  -90.00 -77.00-150.00   62
 36  \w   -149.00-110.00   0.50    0.44    --  -90.00 -77.00 -30.00   78
 37  \w   -158.00-126.00   0.50    0.44    --  -90.00 -77.00   0.00   64
 38  \w   -120.00 -68.00   0.50    0.44    --  -90.00 -77.00   0.00  104
 39  \w   -107.00 -69.00   0.50    0.44    --  -90.00 -77.00 -30.00   76
 40  \w   -105.00 -72.00   0.50    0.44    --  -90.00 -77.00  30.00   66
 41  \w    -99.00 -70.00   0.50    0.44    --  -90.00 -76.00  45.55   58
 42  \w    -87.00 -61.00   0.50    0.44    --  -82.00 -76.00 156.28   52
 43  \w   -150.00-124.00   0.50    0.44    --  -82.00 -76.00 156.28   52
 44  \w    -78.00 -53.00   0.50    0.44    --  -74.00 -75.00 145.99   50
 45  \w   -155.00-120.00   0.50    0.44    --  -90.00 -77.00  30.00   70
 46  \w   -156.00-104.00   0.50    0.44    --  -90.00 -76.00  45.55  104
 47  \w   -136.00-110.00   0.50    0.44    --  -74.00 -75.00 145.99   52
 48  \w    -82.00 -57.00   0.50    0.44    --  -78.00 -74.00 114.61   50
 49  \w    -87.00 -61.00   0.50    0.44    --  -82.00 -75.00  44.84   52
 50  \w    -96.00 -61.00   0.50    0.44    --  -82.00 -74.00  74.73   70
 51  \w    -93.00 -44.00   0.50    0.11    --  -62.00 -73.00 171.95   98
 52  \w   -102.00 -77.00   0.50    0.44    --  -90.00 -73.00 153.25   50
 53  \w   -161.00-107.00   0.50    0.44    --  -90.00 -73.00 153.25  108
 54  \w   -160.00 -70.00   0.50    0.44    --  -90.00 -72.00  91.50  180
 55  \w    -93.00 -62.00   0.50    0.44    --  -82.00 -72.00  57.89   62
 56  \w    -61.00 -35.00   0.50    0.11    --  -54.00 -75.00 -36.76   52
 57  \w    -77.00 -51.00   0.50    0.44    --  -70.00 -72.00 -36.45   52
 58  \w    -91.00 -65.00   0.50    0.44    --  -86.00 -76.00-121.38   52
 59  \w    -86.00 -59.00   0.50    0.44    --  -78.00 -73.00-112.42   54
 60  \w    -84.00 -58.00   0.50    0.44    --  -78.00 -72.00 -61.94   52
 61  \w   -145.00-107.00   0.50    0.44    --  -82.00 -68.00-156.86   76
 62  \w    -93.00 -64.00   0.50    0.44    --  -82.00 -68.00-156.86   58
 63  \w    -85.00 -57.00   0.50    0.44    --  -74.00 -67.00-158.02   56
 64  \w    -83.00 -56.00   0.50    0.44    --  -74.00 -67.00-118.93   54
 65  \w   -106.00 -63.00   0.50    0.44    --  -78.00 -70.00 -27.62   86
 66  \w    -87.00 -54.00   0.50    0.44    --  -70.00 -66.00-151.42   66
 67  \w    -77.00 -52.00   0.50    0.44    --  -70.00 -69.00 -10.19   50
 68  \w   -101.00 -61.00   0.50    0.44    --  -78.00 -66.00  -6.57   80
 69  \w   -144.00-106.00   0.50    0.44    --  -78.00 -65.00-104.12   76
 70  \w   -161.00-127.00   0.50    0.44    --  -90.00 -65.00 -64.24   68
 71  \w   -116.00 -74.00   0.50    0.44    --  -90.00 -65.00 -64.24   84
 72  \w    -86.00 -61.00   0.50    0.44    --  -78.00 -65.00-104.12   50
 73  \w   -160.00-127.00   0.50    0.44    --  -90.00 -60.00-102.81   66
 74  \w   -157.00-124.00   0.50    0.44    --  -90.00 -60.00-126.74   66
 75  \w   -113.00 -76.00   0.50    0.44    --  -90.00 -60.00-126.74   74
 76  \w   -108.00 -83.00   0.50    0.44    --  -90.00 -60.00-102.81   50
 77  \w   -154.00 -85.00   0.50    0.44    --  -90.00 -57.00-180.00  138
 78  \w    -74.00 -48.00   0.50    0.11    --  -66.00 -67.00   3.88   52
 79  \w    -99.00 -72.00   0.50    0.44    --  -90.00 -67.00 116.46   54
 80  \w    -85.00 -59.00   0.50    0.44    --  -78.00 -69.00 169.93   52
 81  \w   -128.00 -77.00   0.50    0.44    --  -90.00 -56.00 110.53  102
 82  \w   -128.00 -94.00   0.50    0.44    --  -90.00 -57.00  60.00   68
 83  \w   -127.00 -95.00   0.50    0.44    --  -90.00-113.00 -54.00   64
 84  \w   -112.00 -84.00   0.50    0.11    --  -47.52 -77.00  60.00   56
 85  \w    -63.00 -27.00   0.50    0.11    --  -47.52 -77.00  60.00   72
 86  \w    -72.00 -37.00   0.50    0.11    --  -47.52 -38.00  60.00   70
 87  \w    -52.00 -26.00   0.50    0.11    --  -47.52 -77.00   0.00   52
 88  \w    -75.00 -45.00   0.50    0.11    --  -47.52 -38.00 -30.00   60
 89  \w   -101.00 -75.00   0.50    0.11    --  -47.52 -77.00-180.00   52
 90  \w    -52.00 -26.00   0.50    0.11    --  -47.52 -77.00-180.00   52
 91  \w     12.00  37.00   0.50    0.11    --   30.00  83.00-140.75   50
 92  \w     13.00  43.00   0.50    0.11    --   38.00  86.00 -70.55   60
 93  \w     69.00 116.00   0.50    0.11    --   47.52 178.00 -60.00   94
 94  \w     -6.00  19.00   0.50    0.11    --   26.00  99.00 107.04   50
 95  \w    -30.00  -4.00   0.50    0.11    --   10.00 112.00 122.04   52
;
_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      -0.0135053000
_diffrn_orient_matrix_UB_12      -0.0576414000
_diffrn_orient_matrix_UB_13      -0.1150680000
_diffrn_orient_matrix_UB_21      0.1237638000
_diffrn_orient_matrix_UB_22      -0.1411960000
_diffrn_orient_matrix_UB_23      0.0172582000
_diffrn_orient_matrix_UB_31      -0.0886002000
_diffrn_orient_matrix_UB_32      -0.1883961000
_diffrn_orient_matrix_UB_33      0.0222677000
_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  0.0521
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19556
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.938
_diffrn_reflns_theta_min         3.399
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.239
_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    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1319 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3246
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0431P)^2^+0.1753P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0824
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                3146
_reflns_number_total             3246
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01416e2.cif
_cod_data_source_block           R-Phenibut_S-Mandelic_Acid
_cod_database_code               7245860
_chemical_oxdiff_formula         'C8H8O3 C10H13NO2'
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.683
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_res_checksum              11626
_shelx_hkl_checksum              64003
_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 1.531
_oxdiff_exptl_absorpt_empirical_full_min 0.589