# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pregabalin
_database_code_depnum_ccdc_archive 'CCDC 2215531'
loop_
_audit_author_name
_audit_author_address
'Petra Bombicz'
;Centre for Structural Science, Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2022-10-26 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_CRYSS02_pregabalin          
;
PROBLEM: The value of _exptl_crystal_size_mid is > 0.8
RESPONSE: The layered structure resulted a pure crystal quality impossible to cut because of the sliding layers. 
;
_vrf_SHFSU01_pregabalin          
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.10
RESPONSE: The crystal was of pure quality. It was not possible to refine the structure to have a better model.
;
_vrf_PLAT080_pregabalin          
;
PROBLEM: Maximum Shift/Error ............................       0.13 Why ?
RESPONSE: The crystal was of pure quality. It was not possible to refine the structure to have a better model.
;
_vrf_PLAT084_pregabalin          
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.27 Report
RESPONSE: The crystal was of pure quality. It was not possible to refine the structure to have a better model.
;
# Added during the CSD deposition process: Wednesday 26 October 2022 06:05 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        '3-(aminomethyl)-5-methylhexanoic acid'
_chemical_name_common            pregabalin
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H17 N O2, H2 O'
_chemical_formula_sum            'C8 H19 N O3'
_chemical_formula_weight         177.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.100(2)
_cell_length_b                   6.259(2)
_cell_length_c                   15.420(2)
_cell_angle_alpha                85.660(2)
_cell_angle_beta                 80.031(2)
_cell_angle_gamma                74.466(2)
_cell_volume                     558.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    7429
_cell_measurement_theta_min      3.380
_cell_measurement_theta_max      25.490

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.054
_exptl_crystal_F_000             196
_exptl_transmission_factor_min   0.92840
_exptl_transmission_factor_max   0.99010
_exptl_crystal_size_max          1.7
_exptl_crystal_size_mid          0.9
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_process_details   
;
  NUMABS, Numerical Absorption correction Program (T.Higashi, 2011)
;
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_detector       RX
_diffrn_measurement_device       RAXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            10890
_diffrn_reflns_av_unetI/netI     0.0969
_diffrn_reflns_av_R_equivalents  0.1050
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.380
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2043
_reflns_number_gt                1395
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_cell_refinement       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_reduction        
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_structure_solution    
;
M.C. Burla  J. Appl. Cryst. (2015). 48, 306--309
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1029P)²+0.4361P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    hetero
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2043
_refine_ls_number_parameters     140
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0921
_refine_ls_wR_factor_ref         0.2678
_refine_ls_wR_factor_gt          0.2419
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0.127
_refine_ls_shift/su_mean         0.015

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0249(4) 1.1932(4) 0.3717(2) 0.0566(9) Uani 1 1 d . . . . .
O2 O -0.1880(4) 0.9569(4) 0.3714(2) 0.0525(8) Uani 1 1 d . . . . .
O3 O 0.7187(5) 0.5674(5) 0.4451(2) 0.0521(8) Uani 1 1 d G . . . .
H3A H 0.825942 0.466801 0.418081 0.078 Uiso 1 1 d G U . . .
N1 N 0.4277(5) 0.3114(5) 0.3774(2) 0.0445(9) Uani 1 1 d . . . . .
H1A H 0.410944 0.394717 0.425137 0.053 Uiso 1 1 calc R U . . .
H1B H 0.555917 0.196183 0.376650 0.053 Uiso 1 1 calc R U . . .
H1C H 0.301726 0.257899 0.380358 0.053 Uiso 1 1 calc R U . . .
C1 C 0.0015(6) 0.9990(6) 0.3700(3) 0.0427(9) Uani 1 1 d . . . . .
C3 C 0.2435(6) 0.6488(6) 0.2924(3) 0.0457(10) Uani 1 1 d . . . . .
H3 H 0.102118 0.592804 0.300243 0.055 Uiso 1 1 calc R U . . .
C4 C 0.4512(6) 0.4499(6) 0.2964(3) 0.0477(10) Uani 1 1 d . . . . .
H4A H 0.471995 0.357522 0.244729 0.057 Uiso 1 1 calc R U . . .
H4B H 0.591127 0.503767 0.292724 0.057 Uiso 1 1 calc R U . . .
C2 C 0.2174(6) 0.8060(6) 0.3671(3) 0.0497(10) Uani 1 1 d . . . . .
H2A H 0.210737 0.721528 0.424021 0.060 Uiso 1 1 calc R U . . .
H2B H 0.354722 0.865554 0.359452 0.060 Uiso 1 1 calc R U . . .
C5 C 0.2647(8) 0.7675(8) 0.2032(3) 0.0634(13) Uani 1 1 d . . . . .
H5A H 0.415891 0.803248 0.191721 0.076 Uiso 1 1 calc R U . . .
H5B H 0.144340 0.910060 0.206767 0.076 Uiso 1 1 calc R U . . .
C6 C 0.2441(11) 0.6454(11) 0.1240(3) 0.0896(18) Uani 1 1 d D U . . .
H6A H 0.381210 0.514313 0.121437 0.107 Uiso 0.53(6) 1 calc R U P A 1
H6B H 0.338536 0.487959 0.119383 0.107 Uiso 0.47(6) 1 calc R U P A 2
C7 C 0.286(9) 0.759(8) 0.0335(16) 0.098(9) Uani 0.53(6) 1 d D U P A 1
H7A H 0.450773 0.749738 0.016994 0.147 Uiso 0.53(6) 1 calc R U P A 1
H7B H 0.198241 0.914598 0.035885 0.147 Uiso 0.53(6) 1 calc R U P A 1
H7C H 0.236313 0.684013 -0.010226 0.147 Uiso 0.53(6) 1 calc R U P A 1
C8 C 0.042(5) 0.536(6) 0.1376(18) 0.115(7) Uani 0.53(6) 1 d . U P A 1
H8A H 0.036498 0.470281 0.082550 0.173 Uiso 0.53(6) 1 calc R U P A 1
H8B H -0.102897 0.647800 0.155076 0.173 Uiso 0.53(6) 1 calc R U P A 1
H8C H 0.064173 0.419358 0.183927 0.173 Uiso 0.53(6) 1 calc R U P A 1
C7' C 0.307(12) 0.810(9) 0.044(2) 0.113(15) Uani 0.47(6) 1 d . U P A 2
H7'A H 0.183662 0.948269 0.046700 0.170 Uiso 0.47(6) 1 calc R U P A 2
H7'B H 0.321885 0.739531 -0.011970 0.170 Uiso 0.47(6) 1 calc R U P A 2
H7'C H 0.452324 0.842537 0.049085 0.170 Uiso 0.47(6) 1 calc R U P A 2
C8' C -0.022(8) 0.680(15) 0.1320(18) 0.149(19) Uani 0.47(6) 1 d . . P A 2
H8'A H -0.058444 0.641591 0.076522 0.224 Uiso 0.47(6) 1 calc R U P A 2
H8'B H -0.101276 0.835240 0.144413 0.224 Uiso 0.47(6) 1 calc R U P A 2
H8'C H -0.074447 0.584090 0.179955 0.224 Uiso 0.47(6) 1 calc R U P A 2
H3B H 0.763(11) 0.691(12) 0.414(4) 0.12(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.264(5) . ?
O2 C1 1.249(4) . ?
O3 H3A 0.8501 . ?
O3 H3B 0.95(7) . ?
N1 C4 1.474(5) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C1 C2 1.527(5) . ?
C3 C5 1.515(6) . ?
C3 C4 1.527(5) . ?
C3 C2 1.532(6) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 C6 1.529(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C8 1.54(3) . ?
C6 C7 1.529(10) . ?
C6 C8' 1.57(4) . ?
C6 C7' 1.61(3) . ?
C6 H6A 1.0000 . ?
C6 H6B 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7' H7'A 0.9800 . ?
C7' H7'B 0.9800 . ?
C7' H7'C 0.9800 . ?
C8' H8'A 0.9800 . ?
C8' H8'B 0.9800 . ?
C8' H8'C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H3A O3 H3B 97.1 . . ?
C4 N1 H1A 109.5 . . ?
C4 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C4 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O2 C1 O1 123.6(3) . . ?
O2 C1 C2 118.5(3) . . ?
O1 C1 C2 117.8(3) . . ?
C5 C3 C4 110.4(3) . . ?
C5 C3 C2 111.4(3) . . ?
C4 C3 C2 110.5(3) . . ?
C5 C3 H3 108.1 . . ?
C4 C3 H3 108.1 . . ?
C2 C3 H3 108.1 . . ?
N1 C4 C3 113.0(3) . . ?
N1 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
N1 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C1 C2 C3 112.5(3) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C3 C5 C6 117.1(4) . . ?
C3 C5 H5A 108.0 . . ?
C6 C5 H5A 108.0 . . ?
C3 C5 H5B 108.0 . . ?
C6 C5 H5B 108.0 . . ?
H5A C5 H5B 107.3 . . ?
C8 C6 C7 115(2) . . ?
C8 C6 C5 115.3(9) . . ?
C7 C6 C5 117(2) . . ?
C5 C6 C8' 103(2) . . ?
C5 C6 C7' 101(2) . . ?
C8' C6 C7' 105(3) . . ?
C8 C6 H6A 102.4 . . ?
C7 C6 H6A 102.4 . . ?
C5 C6 H6A 102.5 . . ?
C5 C6 H6B 115.5 . . ?
C8' C6 H6B 115.3 . . ?
C7' C6 H6B 115.6 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.6 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.4 . . ?
C6 C8 H8B 109.4 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.6 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C7' H7'A 109.5 . . ?
C6 C7' H7'B 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
C6 C7' H7'C 109.4 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
C6 C8' H8'A 109.6 . . ?
C6 C8' H8'B 109.2 . . ?
H8'A C8' H8'B 109.5 . . ?
C6 C8' H8'C 109.6 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C3 C4 N1 -173.0(3) . . . . ?
C2 C3 C4 N1 63.3(4) . . . . ?
O2 C1 C2 C3 52.5(5) . . . . ?
O1 C1 C2 C3 -128.2(4) . . . . ?
C5 C3 C2 C1 61.2(4) . . . . ?
C4 C3 C2 C1 -175.8(3) . . . . ?
C4 C3 C5 C6 68.5(5) . . . . ?
C2 C3 C5 C6 -168.3(4) . . . . ?
C3 C5 C6 C8 46.2(18) . . . . ?
C3 C5 C6 C7 -175(2) . . . . ?
C3 C5 C6 C8' 79(3) . . . . ?
C3 C5 C6 C7' -173(2) . . . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.065



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
