# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_(R)-Pregabalin
_database_code_depnum_ccdc_archive 'CCDC 2170100'
loop_
_audit_author_name
_audit_author_address
'Daniel Komisarek'
;Heinrich Heine University Duesseldorf
Germany
;
_audit_update_record             
;
2022-05-03 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_name_common            (R)-Pregabalin
_chemical_name_systematic        '(R)-3-isobutyl-Î³-aminobutyric acid'
_chemical_formula_moiety         'C8 H17 N O2'
_chemical_formula_sum            'C8 H17 N O2'
_chemical_formula_weight         159.22
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H17 N O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.3684(2)
_cell_length_b                   7.8176(2)
_cell_length_c                   18.5044(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     921.25(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2978
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      76.0830
_cell_measurement_theta_min      4.7400
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.798
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.514
_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_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -1 0 0.1977
0 -5 -3 0.1186
0 5 3 0.1159
-3 3 2 0.2256
-2 1 -11 0.0900
0 -1 -12 0.0578
1 0 12 0.0149
2 0 -10 0.0835
0 2 -11 0.0412

_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.0555 -0.9774 -0.2040 0.1607 0.6856 0.7100
0.2467 -4.8723 -3.2533 0.1870 0.7741 -0.6048
-0.2331 4.8734 3.2525 -0.1875 -0.7760 0.6022
-3.4379 2.6980 1.9124 0.0159 -0.0027 0.9999
-1.6262 0.6676 -10.9350 0.9685 0.0767 0.2367
0.3983 -0.9059 -11.7645 0.9351 0.0764 -0.3461
0.8703 -0.0543 11.7463 -0.9968 -0.0799 -0.0091
2.2567 -0.3056 -10.0418 0.7302 -0.2600 -0.6318
-0.1754 1.9896 -11.0467 0.9401 -0.3310 0.0814

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4569
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.544
_diffrn_reflns_theta_min         4.780
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_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 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    109.00 137.00   0.50    0.25    --  109.41  45.00 -31.00   56
  2  ω    142.00 168.00   0.50    0.25    --  109.41 125.00 -30.00   52
  3  ω     98.00 125.00   0.50    0.25    --  109.41 125.00 -30.00   54
  4  ω    105.00 176.00   0.50    0.25    --  109.41  79.00 157.00  142
  5  ω    -17.00  12.00   0.50    0.06    --   49.27 -19.00  30.00   58
  6  ω    -21.00  38.00   0.50    0.06    --   49.27 -45.00 177.00  118
  7  ω     60.00  91.00   0.50    0.25    --  109.41 -77.00  30.00   62
  8  ω     59.00  84.00   0.50    0.25    --  109.41 -77.00-120.00   50
  9  ω    -21.00   7.00   0.50    0.06    --  -49.27  19.00 -90.00   56
 10  ω    -45.00 -20.00   0.50    0.25    --  -90.00  38.00-180.00   50
 11  ω    -56.00 -19.00   0.50    0.25    --  -90.00  45.00 -31.00   74
 12  ω    -46.00 -21.00   0.50    0.25    --  -90.00  38.00   0.00   50
 13  ω    -47.00 -20.00   0.50    0.25    --  -90.00  38.00  90.00   54
 14  ω    -48.00 -23.00   0.50    0.25    --  -90.00  38.00 150.00   50
 15  ω   -154.00 -79.00   0.50    0.25    --  -90.00 -38.00  90.00  150
 16  ω   -116.00 -91.00   0.50    0.25    --  -90.00-114.00 -46.00   50
 17  ω   -107.00 -74.00   0.50    0.06    --  -49.27-125.00   0.00   66
 18  ω   -116.00 -78.00   0.50    0.06    --  -49.27-125.00 120.00   76
 19  ω    -48.00 -22.00   0.50    0.25    --  -90.00 125.00  60.00   52
 20  ω    -85.00 -51.00   0.50    0.25    --  -90.00 125.00  60.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0389538000
_diffrn_orient_matrix_UB_12      0.0143264000
_diffrn_orient_matrix_UB_13      -0.0819048000
_diffrn_orient_matrix_UB_21      -0.1289694000
_diffrn_orient_matrix_UB_22      -0.1667296000
_diffrn_orient_matrix_UB_23      0.0019821000
_diffrn_orient_matrix_UB_31      -0.2009320000
_diffrn_orient_matrix_UB_32      0.1042122000
_diffrn_orient_matrix_UB_33      0.0145941000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.643
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                1660
_reflns_number_total             1779
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 625 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(19)
_refine_ls_extinction_coef       .
_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     168
_refine_ls_number_reflns         1779
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.053
_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/[σ²(Fo²)+(0.0591P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0995
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.0338(2) 1.05315(18) 0.51530(9) 0.0286(4) Uani 1 1 d . . . . .
O2 O 0.3125(2) 0.96538(19) 0.57764(8) 0.0279(4) Uani 1 1 d . . . . .
N1 N 0.1134(3) 0.3964(2) 0.51309(11) 0.0248(4) Uani 1 1 d . . . . .
C1 C 0.1346(3) 0.9423(3) 0.55154(11) 0.0221(4) Uani 1 1 d . . . . .
C6 C 0.2822(4) 0.5692(3) 0.73331(12) 0.0297(5) Uani 1 1 d . . . . .
C3 C 0.1478(3) 0.6355(2) 0.60356(12) 0.0242(4) Uani 1 1 d . . . . .
C4 C 0.0685(3) 0.4543(3) 0.58833(12) 0.0272(4) Uani 1 1 d . . . . .
C2 C 0.0272(3) 0.7687(3) 0.55973(13) 0.0261(5) Uani 1 1 d . . . . .
C5 C 0.1352(3) 0.6734(3) 0.68455(13) 0.0272(5) Uani 1 1 d . . . . .
C7 C 0.5119(4) 0.5959(4) 0.71345(16) 0.0394(6) Uani 1 1 d . . . . .
C8 C 0.2462(5) 0.6153(4) 0.81208(15) 0.0437(6) Uani 1 1 d . . . . .
H10 H 0.166(4) 0.798(3) 0.6906(14) 0.024(6) Uiso 1 1 d . . . . .
H3 H 0.289(4) 0.641(3) 0.5881(14) 0.024(6) Uiso 1 1 d . . . . .
H11 H 0.255(4) 0.452(4) 0.7295(15) 0.029(6) Uiso 1 1 d . . . . .
H2 H 0.000(5) 0.727(4) 0.5048(17) 0.033(7) Uiso 1 1 d . . . . .
H4 H 0.143(4) 0.372(4) 0.6197(16) 0.035(7) Uiso 1 1 d . . . . .
H17 H 0.099(5) 0.593(5) 0.829(2) 0.051(9) Uiso 1 1 d . . . . .
H5 H -0.088(4) 0.441(4) 0.5958(16) 0.036(7) Uiso 1 1 d . . . . .
H9 H -0.012(4) 0.658(3) 0.7002(15) 0.030(6) Uiso 1 1 d . . . . .
H1 H -0.110(5) 0.792(3) 0.5801(16) 0.031(6) Uiso 1 1 d . . . . .
H6 H 0.248(5) 0.425(4) 0.5017(15) 0.033(7) Uiso 1 1 d . . . . .
H12 H 0.553(6) 0.723(5) 0.710(2) 0.058(10) Uiso 1 1 d . . . . .
H7 H 0.096(4) 0.278(4) 0.5131(15) 0.025(6) Uiso 1 1 d . . . . .
H16 H 0.284(5) 0.730(5) 0.818(2) 0.053(9) Uiso 1 1 d . . . . .
H13 H 0.547(5) 0.552(4) 0.6652(19) 0.046(8) Uiso 1 1 d . . . . .
H8 H 0.023(5) 0.441(4) 0.4796(17) 0.037(7) Uiso 1 1 d . . . . .
H15 H 0.337(6) 0.547(5) 0.851(2) 0.060(9) Uiso 1 1 d . . . . .
H14 H 0.605(5) 0.544(5) 0.7521(19) 0.050(9) 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 1.269(2) . ?
O2 C1 1.245(2) . ?
N1 C4 1.492(3) . ?
N1 H6 0.91(3) . ?
N1 H7 0.93(3) . ?
N1 H8 0.91(3) . ?
C1 C2 1.528(3) . ?
C6 C5 1.535(3) . ?
C6 C7 1.522(4) . ?
C6 C8 1.519(3) . ?
C6 H11 0.94(3) . ?
C3 C4 1.530(3) . ?
C3 C2 1.527(3) . ?
C3 C5 1.530(3) . ?
C3 H3 0.95(3) . ?
C4 H4 0.99(3) . ?
C4 H5 1.01(3) . ?
C2 H2 1.08(3) . ?
C2 H1 0.97(3) . ?
C5 H10 1.00(3) . ?
C5 H9 0.99(3) . ?
C7 H12 1.03(4) . ?
C7 H13 0.98(3) . ?
C7 H14 1.01(3) . ?
C8 H17 1.00(3) . ?
C8 H16 0.94(4) . ?
C8 H15 1.06(4) . ?

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
C4 N1 H6 108.7(18) . . ?
C4 N1 H7 106.1(17) . . ?
C4 N1 H8 113.3(19) . . ?
H6 N1 H7 111(3) . . ?
H6 N1 H8 110(2) . . ?
H7 N1 H8 108(3) . . ?
O1 C1 C2 115.64(16) . . ?
O2 C1 O1 124.48(18) . . ?
O2 C1 C2 119.84(18) . . ?
C5 C6 H11 111.2(15) . . ?
C7 C6 C5 111.8(2) . . ?
C7 C6 H11 107.2(15) . . ?
C8 C6 C5 110.23(19) . . ?
C8 C6 C7 110.1(2) . . ?
C8 C6 H11 106.1(17) . . ?
C4 C3 H3 107.4(15) . . ?
C2 C3 C4 111.56(17) . . ?
C2 C3 C5 111.20(17) . . ?
C2 C3 H3 106.7(16) . . ?
C5 C3 C4 110.03(17) . . ?
C5 C3 H3 109.8(16) . . ?
N1 C4 C3 112.93(17) . . ?
N1 C4 H4 105.0(17) . . ?
N1 C4 H5 106.6(17) . . ?
C3 C4 H4 109.5(16) . . ?
C3 C4 H5 113.2(17) . . ?
H4 C4 H5 109(2) . . ?
C1 C2 H2 104.2(15) . . ?
C1 C2 H1 105.9(16) . . ?
C3 C2 C1 115.69(16) . . ?
C3 C2 H2 112.1(15) . . ?
C3 C2 H1 112.0(17) . . ?
H2 C2 H1 106(2) . . ?
C6 C5 H10 109.4(15) . . ?
C6 C5 H9 109.8(16) . . ?
C3 C5 C6 116.17(18) . . ?
C3 C5 H10 106.8(15) . . ?
C3 C5 H9 108.3(16) . . ?
H10 C5 H9 106(2) . . ?
C6 C7 H12 113(2) . . ?
C6 C7 H13 113.1(18) . . ?
C6 C7 H14 109.5(18) . . ?
H12 C7 H13 103(3) . . ?
H12 C7 H14 106(3) . . ?
H13 C7 H14 112(3) . . ?
C6 C8 H17 114(2) . . ?
C6 C8 H16 108(3) . . ?
C6 C8 H15 116(2) . . ?
H17 C8 H16 111(3) . . ?
H17 C8 H15 102(3) . . ?
H16 C8 H15 105(3) . . ?

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
O1 C1 C2 C3 -179.77(18) . . . . ?
O2 C1 C2 C3 2.5(3) . . . . ?
C4 C3 C2 C1 -161.10(18) . . . . ?
C4 C3 C5 C6 66.7(2) . . . . ?
C2 C3 C4 N1 66.9(2) . . . . ?
C2 C3 C5 C6 -169.13(18) . . . . ?
C5 C3 C4 N1 -169.14(16) . . . . ?
C5 C3 C2 C1 75.6(2) . . . . ?
C7 C6 C5 C3 59.4(3) . . . . ?
C8 C6 C5 C3 -177.74(18) . . . . ?

_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 1.539
_oxdiff_exptl_absorpt_empirical_full_min 0.707
####################################################################### 
# 
# 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_S-PGB_S_Malic_acid
_database_code_depnum_ccdc_archive 'CCDC 2170104'
loop_
_audit_author_name
_audit_author_address
'Daniel Komisarek'
;Heinrich Heine University Duesseldorf
Germany
;
_audit_update_record             
;
2022-05-03 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_name_common            '(S)-Pregabalin (S)-Malic Acid'
_chemical_name_systematic        
'(S)-3-isobutyl-Î³-aminobutyric acid (S)-2-Hydroxysuccinic acid'
_chemical_formula_moiety         'C8 H18 N O2, C4 H5 O5'
_chemical_formula_sum            'C12 H23 N O7'
_chemical_formula_weight         293.31
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H18 N O2 C4 H5 O5'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.50090(10)
_cell_length_b                   7.55810(10)
_cell_length_c                   26.1805(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1484.24(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5790
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.2400
_cell_measurement_theta_min      3.3770
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.797
_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_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -4 -2 0.0975
-4 -3 -3 0.1068
-2 4 3 0.1352
1 5 3 0.0952
4 2 2 0.1068
0 0 -17 0.0093
0 0 17 0.0336

_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.9847 -3.8283 -2.1056 -0.0697 0.8914 0.4478
-3.9074 -2.8220 -2.7143 -0.0377 0.4257 -0.9041
-2.2054 4.3090 2.5896 0.0759 -0.9596 -0.2708
0.9509 4.7053 3.4670 0.0754 -0.9206 0.3831
4.2948 2.2115 2.3616 0.0268 -0.2869 0.9576
0.2983 0.4571 -16.8848 -0.9997 0.0247 -0.0091
-0.0332 -0.4057 16.9316 0.9976 -0.0249 0.0646

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00 -18.00   0.50    3.00    --  -90.00 124.00-146.00  106
  2  ω   -161.00-100.00   0.50    3.00    --  -90.00 -15.00-156.00  122
  3  ω     74.00 107.00   0.50    3.00    --  109.41-113.00  37.00   66
  4  ω     38.00  64.00   0.50    3.00    --  109.41-113.00  37.00   52
  5  ω    -26.00   7.00   0.50    1.00    --  -49.27  19.00 150.00   66
  6  ω   -122.00 -46.00   0.50    1.00    --  -49.27 -15.00-156.00  152
  7  ω    -22.00   7.00   0.50    1.00    --   49.27 -19.00 120.00   58
  8  ω     43.00  69.00   0.50    1.00    --   49.27-124.00 134.00   52
  9  ω    -47.00 -18.00   0.50    3.00    --  -90.00  38.00-150.00   58
 10  ω    -48.00 -22.00   0.50    3.00    --  -90.00  38.00 150.00   52
 11  ω    -48.00 -22.00   0.50    3.00    --  -90.00  38.00-120.00   52
 12  ω    -44.00 -19.00   0.50    3.00    --  -90.00 125.00  30.00   50
 13  ω    -48.00 -23.00   0.50    3.00    --  -90.00  38.00   0.00   50
 14  ω    -48.00 -23.00   0.50    3.00    --  -90.00  38.00  90.00   50
 15  ω    -83.00 -58.00   0.50    3.00    --  -90.00 125.00  30.00   50
 16  ω    -71.00 -29.00   0.50    3.00    --  -90.00  57.00 150.00   84
 17  ω   -159.00-133.00   0.50    3.00    --  -90.00 -99.00  30.00   52
 18  ω   -128.00-102.00   0.50    3.00    --  -90.00 -99.00  30.00   52
 19  ω     41.00  84.00   0.50    3.00    --  109.41-124.00 134.00   86
 20  ω     44.00  69.00   0.50    3.00    --  109.41 -77.00 120.00   50
 21  ω     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       'ω 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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_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_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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_coef       .
_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_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0249
_refine_ls_restrained_S_all      1.053
_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/[σ²(Fo²)+(0.0277P)²+0.3039P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0594
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O3B O 0.64195(16) 0.46189(16) 0.30977(5) 0.0152(3) Uani 1 1 d . . . . .
O2B O 1.04061(16) 0.26488(16) 0.37258(4) 0.0170(3) Uani 1 1 d . . . . .
O5B O 0.92561(16) 0.83435(16) 0.33117(5) 0.0168(3) Uani 1 1 d . . . . .
O1B O 0.91689(16) 0.14278(16) 0.30294(5) 0.0167(3) Uani 1 1 d . . . . .
O4B O 0.70471(16) 0.79615(15) 0.27454(4) 0.0145(3) Uani 1 1 d . . . . .
O1A O 0.14365(17) 0.58113(18) 0.41373(5) 0.0193(3) Uani 1 1 d . . . . .
O2A O 0.34440(16) 0.59866(19) 0.35127(5) 0.0235(3) Uani 1 1 d . . . . .
N1A N 0.5055(2) 1.0972(2) 0.29218(6) 0.0143(3) Uani 1 1 d . . . . .
C4B C 0.8083(2) 0.7426(2) 0.30850(6) 0.0125(3) Uani 1 1 d . . . . .
C1B C 0.9765(2) 0.2755(2) 0.32923(6) 0.0128(3) Uani 1 1 d . . . . .
C1A C 0.2681(2) 0.6656(2) 0.38757(7) 0.0157(4) Uani 1 1 d . . . . .
C3B C 0.7999(2) 0.5502(2) 0.32586(6) 0.0124(3) Uani 1 1 d . . . . .
C3A C 0.4502(2) 0.9502(2) 0.37764(6) 0.0147(3) Uani 1 1 d . . . . .
C2B C 0.9571(2) 0.4510(2) 0.30271(6) 0.0133(3) Uani 1 1 d . . . . .
C2A C 0.3056(2) 0.8493(2) 0.40725(7) 0.0175(4) Uani 1 1 d . . . . .
C5A C 0.5207(2) 1.1105(2) 0.40752(7) 0.0173(4) Uani 1 1 d . . . . .
C6A C 0.6071(2) 1.0741(3) 0.45961(7) 0.0198(4) Uani 1 1 d . . . . .
C4A C 0.3725(2) 1.0091(2) 0.32639(7) 0.0162(4) Uani 1 1 d . . . . .
C7A C 0.6765(3) 1.2484(3) 0.48145(8) 0.0286(5) Uani 1 1 d . . . . .
C8A C 0.7568(3) 0.9385(3) 0.45596(8) 0.0280(5) Uani 1 1 d . . . . .
H12A H 0.512(3) 1.032(3) 0.4839(8) 0.017(5) Uiso 1 1 d . . . . .
H2A H 0.193(3) 0.915(3) 0.4069(8) 0.024(5) Uiso 1 1 d . . . . .
H3A H 0.339(3) 0.832(3) 0.4430(9) 0.021(5) Uiso 1 1 d . . . . .
H5A H 0.323(3) 0.906(3) 0.3078(8) 0.016(5) Uiso 1 1 d . . . . .
H15A H 0.721(3) 1.232(3) 0.5183(10) 0.031(6) Uiso 1 1 d . . . . .
H4A H 0.550(3) 0.868(3) 0.3717(8) 0.018(5) Uiso 1 1 d . . . . .
H4B H 0.810(2) 0.553(3) 0.3643(7) 0.009(4) Uiso 1 1 d . . . . .
H3B H 1.064(3) 0.519(3) 0.3083(8) 0.013(5) Uiso 1 1 d . . . . .
H5B H 0.556(4) 0.508(3) 0.3229(9) 0.031(7) Uiso 1 1 d . . . . .
H11A H 0.613(3) 1.170(3) 0.3866(9) 0.026(6) Uiso 1 1 d . . . . .
H8A H 0.563(3) 1.194(3) 0.3062(9) 0.031(6) Uiso 1 1 d . . . . .
H16A H 0.715(4) 0.819(4) 0.4464(10) 0.035(6) Uiso 1 1 d . . . . .
H6A H 0.275(3) 1.094(3) 0.3320(8) 0.020(5) Uiso 1 1 d . . . . .
H2B H 0.934(3) 0.429(3) 0.2662(7) 0.012(5) Uiso 1 1 d . . . . .
H7A H 0.448(3) 1.139(3) 0.2646(10) 0.034(7) Uiso 1 1 d . . . . .
H17A H 0.818(3) 0.929(3) 0.4896(9) 0.032(6) Uiso 1 1 d . . . . .
H1A H 0.124(4) 0.471(5) 0.4022(12) 0.060(9) Uiso 1 1 d . . . . .
H18A H 0.847(3) 0.978(3) 0.4303(9) 0.031(6) Uiso 1 1 d . . . . .
H14A H 0.583(4) 1.341(4) 0.4824(11) 0.049(8) Uiso 1 1 d . . . . .
H10A H 0.422(3) 1.202(3) 0.4122(8) 0.024(5) Uiso 1 1 d . . . . .
H13A H 0.776(4) 1.292(4) 0.4606(10) 0.038(7) Uiso 1 1 d . . . . .
H9A H 0.590(3) 1.014(3) 0.2834(9) 0.026(6) Uiso 1 1 d . . . . .
H1B H 0.927(4) 0.012(5) 0.3178(13) 0.073(10) 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
O3B C3B 1.423(2) . ?
O3B H5B 0.81(3) . ?
O2B C1B 1.235(2) . ?
O5B C4B 1.268(2) . ?
O1B C1B 1.296(2) . ?
O1B H1B 1.06(4) . ?
O4B C4B 1.249(2) . ?
O1A C1A 1.322(2) . ?
O1A H1A 0.90(3) . ?
O2A C1A 1.219(2) . ?
N1A C4A 1.497(2) . ?
N1A H8A 0.92(3) . ?
N1A H7A 0.90(3) . ?
N1A H9A 0.92(2) . ?
C4B C3B 1.525(2) . ?
C1B C2B 1.504(2) . ?
C1A C2A 1.507(2) . ?
C3B C2B 1.523(2) . ?
C3B H4B 1.010(18) . ?
C3A C2A 1.536(2) . ?
C3A C5A 1.536(2) . ?
C3A C4A 1.529(2) . ?
C3A H4A 0.98(2) . ?
C2B H3B 0.97(2) . ?
C2B H2B 0.985(19) . ?
C2A H2A 0.98(2) . ?
C2A H3A 0.98(2) . ?
C5A C6A 1.535(2) . ?
C5A H11A 0.99(2) . ?
C5A H10A 1.02(2) . ?
C6A C7A 1.528(3) . ?
C6A C8A 1.523(3) . ?
C6A H12A 1.01(2) . ?
C4A H5A 0.99(2) . ?
C4A H6A 0.98(2) . ?
C7A H15A 1.03(2) . ?
C7A H14A 0.99(3) . ?
C7A H13A 0.98(3) . ?
C8A H16A 0.99(3) . ?
C8A H17A 1.00(2) . ?
C8A H18A 1.00(3) . ?

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
C3B O3B H5B 109.6(18) . . ?
C1B O1B H1B 120.0(18) . . ?
C1A O1A H1A 113(2) . . ?
C4A N1A H8A 115.0(15) . . ?
C4A N1A H7A 108.6(16) . . ?
C4A N1A H9A 107.6(14) . . ?
H8A N1A H7A 105(2) . . ?
H8A N1A H9A 109(2) . . ?
H7A N1A H9A 112(2) . . ?
O5B C4B C3B 114.28(14) . . ?
O4B C4B O5B 126.02(15) . . ?
O4B C4B C3B 119.71(14) . . ?
O2B C1B O1B 124.87(15) . . ?
O2B C1B C2B 121.29(15) . . ?
O1B C1B C2B 113.82(14) . . ?
O1A C1A C2A 113.56(15) . . ?
O2A C1A O1A 122.31(16) . . ?
O2A C1A C2A 124.13(16) . . ?
O3B C3B C4B 113.18(13) . . ?
O3B C3B C2B 107.19(13) . . ?
O3B C3B H4B 111.5(11) . . ?
C4B C3B H4B 105.8(11) . . ?
C2B C3B C4B 108.58(13) . . ?
C2B C3B H4B 110.6(11) . . ?
C2A C3A C5A 112.20(14) . . ?
C2A C3A H4A 107.7(12) . . ?
C5A C3A H4A 108.4(12) . . ?
C4A C3A C2A 108.57(14) . . ?
C4A C3A C5A 110.41(14) . . ?
C4A C3A H4A 109.5(12) . . ?
C1B C2B C3B 109.00(13) . . ?
C1B C2B H3B 108.8(12) . . ?
C1B C2B H2B 108.6(12) . . ?
C3B C2B H3B 108.6(12) . . ?
C3B C2B H2B 109.6(11) . . ?
H3B C2B H2B 112.3(16) . . ?
C1A C2A C3A 114.63(15) . . ?
C1A C2A H2A 107.6(13) . . ?
C1A C2A H3A 104.7(13) . . ?
C3A C2A H2A 110.6(13) . . ?
C3A C2A H3A 111.6(13) . . ?
H2A C2A H3A 107.2(18) . . ?
C3A C5A H11A 108.6(13) . . ?
C3A C5A H10A 110.2(13) . . ?
C6A C5A C3A 117.17(15) . . ?
C6A C5A H11A 106.1(13) . . ?
C6A C5A H10A 108.7(13) . . ?
H11A C5A H10A 105.4(18) . . ?
C5A C6A H12A 108.6(12) . . ?
C7A C6A C5A 108.79(16) . . ?
C7A C6A H12A 106.3(12) . . ?
C8A C6A C5A 112.07(15) . . ?
C8A C6A C7A 110.63(17) . . ?
C8A C6A H12A 110.3(12) . . ?
N1A C4A C3A 113.61(14) . . ?
N1A C4A H5A 107.8(12) . . ?
N1A C4A H6A 107.3(13) . . ?
C3A C4A H5A 110.1(12) . . ?
C3A C4A H6A 110.0(12) . . ?
H5A C4A H6A 107.8(17) . . ?
C6A C7A H15A 111.1(15) . . ?
C6A C7A H14A 112.1(17) . . ?
C6A C7A H13A 110.1(15) . . ?
H15A C7A H14A 107(2) . . ?
H15A C7A H13A 108(2) . . ?
H14A C7A H13A 108(2) . . ?
C6A C8A H16A 113.3(16) . . ?
C6A C8A H17A 109.5(14) . . ?
C6A C8A H18A 109.9(15) . . ?
H16A C8A H17A 108(2) . . ?
H16A C8A H18A 108(2) . . ?
H17A C8A H18A 107.7(19) . . ?

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
O3B C3B C2B C1B -71.12(16) . . . . ?
O2B C1B C2B C3B -75.57(19) . . . . ?
O5B C4B C3B O3B 165.34(14) . . . . ?
O5B C4B C3B C2B -75.77(17) . . . . ?
O1B C1B C2B C3B 102.94(16) . . . . ?
O4B C4B C3B O3B -14.8(2) . . . . ?
O4B C4B C3B C2B 104.08(17) . . . . ?
O1A C1A C2A C3A 179.80(14) . . . . ?
O2A C1A C2A C3A 0.2(3) . . . . ?
C4B C3B C2B C1B 166.28(13) . . . . ?
C3A C5A C6A C7A 177.01(16) . . . . ?
C3A C5A C6A C8A 54.4(2) . . . . ?
C2A C3A C5A C6A 60.0(2) . . . . ?
C2A C3A C4A N1A -175.53(14) . . . . ?
C5A C3A C2A C1A -163.60(15) . . . . ?
C5A C3A C4A N1A 61.08(19) . . . . ?
C4A C3A C2A C1A 74.10(19) . . . . ?
C4A C3A C5A C6A -178.77(15) . . . . ?

_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
####################################################################### 
# 
# 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_S-Pregabalin_R-Malic_Acid
_database_code_depnum_ccdc_archive 'CCDC 2170106'
loop_
_audit_author_name
_audit_author_address
'Daniel Komisarek'
;Heinrich Heine University Duesseldorf
Germany
;
_audit_update_record             
;
2022-05-03 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_name_common            '(S)-Pregabalin (R)-Malic Acid'
_chemical_name_systematic        
'(S)-3-isobutyl-Î³-aminobutyric acid (R)-2-Hydroxysuccinic acid'
_chemical_formula_moiety         'C8 H18 N O2, C4 H5 O5'
_chemical_formula_sum            'C12 H23 N O7'
_chemical_formula_weight         293.31
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H17 N O2 C4 H5 O5'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.44040(10)
_cell_length_b                   7.70390(10)
_cell_length_c                   25.9566(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1487.83(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18167
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.5860
_cell_measurement_theta_min      5.9410
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.735
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.500
_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_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate'
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.1703
-1 5 1 0.0702
-5 0 -5 0.1386
1 -5 -2 0.0830
3 3 9 0.1298
0 0 17 0.0254
-3 -3 -8 0.1258
0 0 -17 0.0461
0 -3 -14 0.0504
2 -1 -15 0.0923

_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0009 -0.0003 0.9971 0.0379 0.1578 0.1419
-0.8622 4.9061 1.2750 -0.1798 -0.7431 0.6446
-4.6468 -0.0513 -4.5874 -0.1706 -0.7263 -0.6659
0.5026 -4.9498 -1.6473 0.1678 0.6918 -0.7023
2.6745 3.2717 8.6778 0.2639 -0.0103 0.9645
0.3763 -0.0998 16.7928 0.9527 -0.0247 0.3028
-2.7548 -3.4148 -7.6905 -0.1984 0.0088 -0.9801
-0.2183 0.3116 -16.7976 -0.9676 0.0249 -0.2514
0.0162 -2.6364 -14.3137 -0.6695 0.4060 -0.6220
1.9502 -0.8994 -15.1106 -0.8462 0.5162 -0.1323

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            22743
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.790
_diffrn_reflns_theta_min         5.992
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00 102.00   0.50    0.10    --   49.27  55.00 137.00  132
  2  ω    104.00 129.00   0.50    0.20    --  109.41  19.00  90.00   50
  3  ω    152.00 178.00   0.50    0.20    --  109.41  19.00  90.00   52
  4  ω    101.00 141.00   0.50    0.20    --  109.41  71.00 -18.00   80
  5  ω     90.00 122.00   0.50    0.20    --  109.41  77.00 -30.00   64
  6  ω    125.00 168.00   0.50    0.20    --  109.41  38.00 -60.00   86
  7  ω    136.00 169.00   0.50    0.20    --  109.41  19.00-150.00   66
  8  ω    -93.00 -31.00   0.50    0.20    --  -90.00  71.00 -17.00  124
  9  ω    -49.00 -24.00   0.50    0.20    --  -90.00  54.00 -70.30   50
 10  ω    -48.00 -18.00   0.50    0.20    --  -90.00  57.00 -60.00   60
 11  ω    -48.00 -23.00   0.50    0.20    --  -90.00  38.00 -90.00   50
 12  ω    -48.00 -23.00   0.50    0.20    --  -90.00  38.00   0.00   50
 13  ω    -54.00 -21.00   0.50    0.20    --  -90.00  57.00  60.00   66
 14  ω    -68.00 -26.00   0.50    0.20    --  -90.00  55.00 137.00   84
 15  ω    -48.00 -23.00   0.50    0.20    --  -90.00  38.00  90.00   50
 16  ω    -48.00 -23.00   0.50    0.20    --  -90.00  38.00  30.00   50
 17  ω    -48.00 -23.00   0.50    0.20    --  -90.00  38.00-150.00   50
 18  ω    -61.00   1.00   0.50    0.10    --  -49.27 104.00-135.00  124
 19  ω   -117.00 -68.00   0.50    0.20    --  -90.00 -77.00-180.00   98
 20  ω    -95.00 -70.00   0.50    0.20    --  -90.00 -74.00-140.56   50
 21  ω   -136.00 -74.00   0.50    0.20    --  -90.00 -71.00-148.00  124
 22  ω    -94.00 -68.00   0.50    0.20    --  -90.00 -77.00 -60.00   52
 23  ω   -101.00 -73.00   0.50    0.20    --  -90.00 -66.00 -66.44   56
 24  ω   -105.00 -76.00   0.50    0.20    --  -90.00 -57.00 -30.00   58
 25  ω   -161.00-127.00   0.50    0.20    --  -90.00 -57.00 -90.00   68
 26  ω   -158.00-132.00   0.50    0.20    --  -90.00 -66.00 -66.44   52
 27  ω   -115.00 -90.00   0.50    0.20    --  -90.00 -57.00 -90.00   50
 28  ω   -158.00-112.00   0.50    0.20    --  -90.00 -57.00 -30.00   92
 29  ω   -146.00 -80.00   0.50    0.20    --  -90.00 -38.00 -90.00  132
 30  ω   -153.00 -77.00   0.50    0.20    --  -90.00 -55.00  -5.00  152
 31  ω   -122.00 -83.00   0.50    0.20    --  -90.00 -38.00  30.00   78
 32  ω   -110.00 -80.00   0.50    0.20    --  -90.00 -15.00  43.49   60
 33  ω   -162.00-115.00   0.50    0.20    --  -90.00 -15.00  43.49   94
 34  ω   -155.00 -70.00   0.50    0.20    --  -90.00 -73.00 165.36  170
 35  ω   -118.00 -75.00   0.50    0.20    --  -90.00 -61.00 179.29   86
 36  ω   -111.00 -86.00   0.50    0.20    --  -90.00 -99.00  90.00   50
 37  ω   -113.00 -84.00   0.50    0.20    --  -90.00-104.00 123.00   58
 38  ω   -148.00-122.00   0.50    0.20    --  -90.00-104.00 123.00   52
 39  ω   -121.00 -90.00   0.50    0.20    --  -90.00 -99.00 150.00   62
 40  ω   -111.00 -82.00   0.50    0.10    --  -49.27-125.00 -60.00   58
 41  ω   -102.00 -73.00   0.50    0.10    --  -49.27-125.00 -90.00   58
 42  ω   -160.00-130.00   0.50    0.20    --  -90.00 -99.00-180.00   60
 43  ω    -11.00  15.00   0.50    0.10    --   49.27 -19.00 -90.00   52
 44  ω    -10.00  17.00   0.50    0.10    --   49.27 -19.00-150.00   54
 45  ω     45.00  83.00   0.50    0.20    --  109.41 -71.00-148.00   76
 46  ω    -18.00  10.00   0.50    0.10    --   49.27 -19.00  30.00   56
 47  ω     51.00  98.00   0.50    0.20    --  109.41 -99.00 -60.00   94
 48  ω     66.00 100.00   0.50    0.20    --  109.41-124.00 -18.47   68
 49  ω     41.00  74.00   0.50    0.20    --  109.41-125.00  60.00   66
 50  ω     37.00  97.00   0.50    0.20    --  109.41-104.00 123.00  120
 51  ω     39.00  69.00   0.50    0.20    --  109.41 -99.00-180.00   60
 52  ω     81.00 107.00   0.50    0.20    --  109.41-103.00-171.03   52
 53  ω     76.00 105.00   0.50    0.20    --  109.41 -99.00-180.00   58
 54  ω     43.00  91.00   0.50    0.20    --  109.41 -99.00-150.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0187930000
_diffrn_orient_matrix_UB_12      -0.0547217000
_diffrn_orient_matrix_UB_13      0.0568311000
_diffrn_orient_matrix_UB_21      0.1634238000
_diffrn_orient_matrix_UB_22      -0.1212174000
_diffrn_orient_matrix_UB_23      -0.0058544000
_diffrn_orient_matrix_UB_31      0.1257511000
_diffrn_orient_matrix_UB_32      0.1493027000
_diffrn_orient_matrix_UB_33      0.0160996000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                2947
_reflns_number_total             3009
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1174 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3009
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.109
_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/[σ²(Fo²)+(0.0294P)²+0.6823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0778
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1B O 0.4684(2) 0.16161(19) 0.67623(6) 0.0187(3) Uani 1 1 d . . . . .
O4B O 0.3629(2) 0.85755(19) 0.68193(6) 0.0195(3) Uani 1 1 d . . . . .
O3B O 0.1476(2) 0.58774(19) 0.68779(6) 0.0181(3) Uani 1 1 d . . . . .
O5B O 0.5542(2) 0.7259(2) 0.62808(6) 0.0203(3) Uani 1 1 d . . . . .
O2B O 0.2355(2) 0.21645(19) 0.72854(6) 0.0191(3) Uani 1 1 d . . . . .
O1A O 0.6510(2) 0.4287(2) 0.58866(6) 0.0224(3) Uani 1 1 d . . . . .
O2A O 0.8669(2) 0.4115(2) 0.64834(6) 0.0256(4) Uani 1 1 d . . . . .
N1A N 1.0004(2) -0.0694(2) 0.71065(7) 0.0162(4) Uani 1 1 d . . . . .
C4B C 0.4210(3) 0.7273(3) 0.65752(7) 0.0156(4) Uani 1 1 d . . . . .
C1B C 0.3713(3) 0.2628(3) 0.70489(7) 0.0152(4) Uani 1 1 d . . . . .
C1A C 0.7824(3) 0.3478(3) 0.61286(8) 0.0183(4) Uani 1 1 d . . . . .
C3A C 0.9532(3) 0.0608(3) 0.62259(8) 0.0168(4) Uani 1 1 d . . . . .
C6A C 1.1071(3) -0.0698(3) 0.54057(8) 0.0217(5) Uani 1 1 d . . . . .
C5A C 1.0121(3) -0.1007(3) 0.59220(8) 0.0187(4) Uani 1 1 d . . . . .
C2B C 0.4336(3) 0.4490(3) 0.70547(8) 0.0160(4) Uani 1 1 d . . . . .
C3B C 0.3221(3) 0.5552(3) 0.66688(8) 0.0153(4) Uani 1 1 d . . . . .
C2A C 0.8171(3) 0.1682(3) 0.59171(8) 0.0193(4) Uani 1 1 d . . . . .
C4A C 0.8676(3) 0.0079(3) 0.67388(8) 0.0181(4) Uani 1 1 d . . . . .
C7A C 1.2668(3) 0.0540(4) 0.54546(10) 0.0284(5) Uani 1 1 d . . . . .
C8A C 1.1686(3) -0.2439(4) 0.51885(10) 0.0276(5) Uani 1 1 d . . . . .
H2A H 0.852(4) 0.182(4) 0.5552(10) 0.024(7) Uiso 1 1 d . . . . .
H2B H 0.414(3) 0.503(3) 0.7403(9) 0.015(6) Uiso 1 1 d . . . . .
H10A H 1.094(4) -0.174(4) 0.6137(10) 0.025(7) Uiso 1 1 d . . . . .
H17A H 1.211(4) -0.229(4) 0.4824(11) 0.029(7) Uiso 1 1 d . . . . .
H9A H 1.055(4) -0.159(4) 0.6977(10) 0.025(7) Uiso 1 1 d . . . . .
H4B H 0.314(3) 0.499(3) 0.6334(8) 0.004(5) Uiso 1 1 d . . . . .
H3B H 0.559(4) 0.450(3) 0.6963(9) 0.019(6) Uiso 1 1 d . . . . .
H7A H 0.955(4) -0.103(4) 0.7393(12) 0.036(8) Uiso 1 1 d . . . . .
H15A H 1.322(4) 0.067(4) 0.5109(11) 0.029(7) Uiso 1 1 d . . . . .
H8A H 1.089(4) 0.011(4) 0.7195(10) 0.022(7) Uiso 1 1 d . . . . .
H4A H 1.056(4) 0.133(4) 0.6291(10) 0.022(6) Uiso 1 1 d . . . . .
H11A H 0.901(3) -0.181(3) 0.5872(9) 0.017(6) Uiso 1 1 d . . . . .
H18A H 1.068(4) -0.326(4) 0.5176(11) 0.033(8) Uiso 1 1 d . . . . .
H16A H 1.263(4) -0.306(4) 0.5405(12) 0.034(8) Uiso 1 1 d . . . . .
H1A H 0.623(5) 0.541(5) 0.6036(14) 0.060(11) Uiso 1 1 d . . . . .
H5A H 0.823(3) 0.112(3) 0.6916(9) 0.017(6) Uiso 1 1 d . . . . .
H14A H 1.235(4) 0.173(4) 0.5555(12) 0.032(8) Uiso 1 1 d . . . . .
H12A H 1.017(4) -0.021(4) 0.5149(10) 0.030(7) Uiso 1 1 d . . . . .
H1B H 0.434(5) 0.050(5) 0.6769(14) 0.056(10) Uiso 1 1 d . . . . .
H6A H 0.779(4) -0.077(4) 0.6675(10) 0.020(6) Uiso 1 1 d . . . . .
H5B H 0.072(6) 0.524(5) 0.6721(15) 0.063(12) Uiso 1 1 d . . . . .
H13A H 1.351(5) 0.009(5) 0.5726(12) 0.044(9) Uiso 1 1 d . . . . .
H3A H 0.700(4) 0.111(4) 0.5902(12) 0.033(8) 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
O1B C1B 1.297(3) . ?
O1B H1B 0.90(4) . ?
O4B C4B 1.263(3) . ?
O3B C3B 1.429(2) . ?
O3B H5B 0.85(4) . ?
O5B C4B 1.251(3) . ?
O2B C1B 1.235(3) . ?
O1A C1A 1.319(3) . ?
O1A H1A 0.97(4) . ?
O2A C1A 1.218(3) . ?
N1A C4A 1.497(3) . ?
N1A H9A 0.87(3) . ?
N1A H7A 0.85(3) . ?
N1A H8A 0.93(3) . ?
C4B C3B 1.536(3) . ?
C1B C2B 1.508(3) . ?
C1A C2A 1.511(3) . ?
C3A C5A 1.537(3) . ?
C3A C2A 1.534(3) . ?
C3A C4A 1.531(3) . ?
C3A H4A 0.97(3) . ?
C6A C5A 1.534(3) . ?
C6A C7A 1.530(3) . ?
C6A C8A 1.525(3) . ?
C6A H12A 1.02(3) . ?
C5A H10A 1.00(3) . ?
C5A H11A 1.04(3) . ?
C2B C3B 1.536(3) . ?
C2B H2B 1.01(2) . ?
C2B H3B 0.96(3) . ?
C3B H4B 0.97(2) . ?
C2A H2A 0.99(3) . ?
C2A H3A 0.97(3) . ?
C4A H5A 0.98(3) . ?
C4A H6A 0.94(3) . ?
C7A H15A 0.99(3) . ?
C7A H14A 0.98(3) . ?
C7A H13A 1.00(3) . ?
C8A H17A 1.00(3) . ?
C8A H18A 0.98(3) . ?
C8A H16A 1.02(3) . ?

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
C1B O1B H1B 114(2) . . ?
C3B O3B H5B 109(3) . . ?
C1A O1A H1A 113(2) . . ?
C4A N1A H9A 112.2(18) . . ?
C4A N1A H7A 115(2) . . ?
C4A N1A H8A 111.1(17) . . ?
H9A N1A H7A 106(3) . . ?
H9A N1A H8A 107(3) . . ?
H7A N1A H8A 105(3) . . ?
O4B C4B C3B 116.27(18) . . ?
O5B C4B O4B 125.8(2) . . ?
O5B C4B C3B 117.94(18) . . ?
O1B C1B C2B 113.98(18) . . ?
O2B C1B O1B 124.56(19) . . ?
O2B C1B C2B 121.41(18) . . ?
O1A C1A C2A 112.75(18) . . ?
O2A C1A O1A 123.5(2) . . ?
O2A C1A C2A 123.7(2) . . ?
C5A C3A H4A 109.5(16) . . ?
C2A C3A C5A 110.90(17) . . ?
C2A C3A H4A 107.7(16) . . ?
C4A C3A C5A 110.45(17) . . ?
C4A C3A C2A 108.88(17) . . ?
C4A C3A H4A 109.4(15) . . ?
C5A C6A H12A 109.1(16) . . ?
C7A C6A C5A 112.48(19) . . ?
C7A C6A H12A 109.6(17) . . ?
C8A C6A C5A 109.0(2) . . ?
C8A C6A C7A 110.3(2) . . ?
C8A C6A H12A 106.2(16) . . ?
C3A C5A H10A 110.0(15) . . ?
C3A C5A H11A 108.7(14) . . ?
C6A C5A C3A 117.04(18) . . ?
C6A C5A H10A 107.2(16) . . ?
C6A C5A H11A 110.5(14) . . ?
H10A C5A H11A 103(2) . . ?
C1B C2B C3B 109.52(17) . . ?
C1B C2B H2B 111.0(14) . . ?
C1B C2B H3B 107.4(16) . . ?
C3B C2B H2B 106.7(14) . . ?
C3B C2B H3B 111.1(15) . . ?
H2B C2B H3B 111(2) . . ?
O3B C3B C4B 110.10(16) . . ?
O3B C3B C2B 109.66(16) . . ?
O3B C3B H4B 111.0(13) . . ?
C4B C3B C2B 107.71(16) . . ?
C4B C3B H4B 106.0(13) . . ?
C2B C3B H4B 112.3(13) . . ?
C1A C2A C3A 114.65(18) . . ?
C1A C2A H2A 107.1(17) . . ?
C1A C2A H3A 106.1(18) . . ?
C3A C2A H2A 112.6(17) . . ?
C3A C2A H3A 111.4(18) . . ?
H2A C2A H3A 104(2) . . ?
N1A C4A C3A 112.70(17) . . ?
N1A C4A H5A 104.5(14) . . ?
N1A C4A H6A 107.4(16) . . ?
C3A C4A H5A 109.3(15) . . ?
C3A C4A H6A 108.8(15) . . ?
H5A C4A H6A 114(2) . . ?
C6A C7A H15A 108.0(17) . . ?
C6A C7A H14A 114.6(19) . . ?
C6A C7A H13A 109(2) . . ?
H15A C7A H14A 104(2) . . ?
H15A C7A H13A 114(3) . . ?
H14A C7A H13A 107(3) . . ?
C6A C8A H17A 109.9(17) . . ?
C6A C8A H18A 110.6(18) . . ?
C6A C8A H16A 114.5(18) . . ?
H17A C8A H18A 107(2) . . ?
H17A C8A H16A 111(2) . . ?
H18A C8A H16A 104(2) . . ?

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
O1B C1B C2B C3B 97.4(2) . . . . ?
O4B C4B C3B O3B 19.7(2) . . . . ?
O4B C4B C3B C2B -99.8(2) . . . . ?
O5B C4B C3B O3B -162.58(17) . . . . ?
O5B C4B C3B C2B 77.9(2) . . . . ?
O2B C1B C2B C3B -80.1(2) . . . . ?
O1A C1A C2A C3A -173.13(18) . . . . ?
O2A C1A C2A C3A 7.1(3) . . . . ?
C1B C2B C3B O3B 75.6(2) . . . . ?
C1B C2B C3B C4B -164.58(16) . . . . ?
C5A C3A C2A C1A -167.14(18) . . . . ?
C5A C3A C4A N1A 68.4(2) . . . . ?
C2A C3A C5A C6A 61.4(2) . . . . ?
C2A C3A C4A N1A -169.56(17) . . . . ?
C4A C3A C5A C6A -177.77(18) . . . . ?
C4A C3A C2A C1A 71.1(2) . . . . ?
C7A C6A C5A C3A 52.6(3) . . . . ?
C8A C6A C5A C3A 175.18(19) . . . . ?

_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 1.237
_oxdiff_exptl_absorpt_empirical_full_min 0.823
####################################################################### 
# 
# 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_S-PGB
_database_code_depnum_ccdc_archive 'CCDC 2170105'
loop_
_audit_author_name
_audit_author_address
'Daniel Komisarek'
;Heinrich Heine University Duesseldorf
Germany
;
_audit_update_record             
;
2022-05-03 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_name_common            (S)-Pregabalin
_chemical_name_systematic        '(S)-3-isobutyl-Î³-aminobutyric acid'
_chemical_formula_moiety         'C8 H17 N O2'
_chemical_formula_sum            'C8 H17 N O2'
_chemical_formula_weight         159.22
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H17 N O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.3444(2)
_cell_length_b                   7.8094(3)
_cell_length_c                   18.4933(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     916.27(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5024
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      77.3240
_cell_measurement_theta_min      4.7360
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.817
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.622
_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_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -5 3 0.1623
0 5 -3 0.1273
4 0 1 0.0389
-4 1 -2 0.1177
1 0 -12 0.0118
-1 0 12 0.0136

_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0889 -4.7360 2.8757 0.0063 0.0433 -0.9990
-0.0368 4.8728 -3.3076 -0.0697 -0.3084 0.9487
4.0964 0.0807 1.1803 0.2227 0.9288 0.2961
-3.9791 1.0236 -1.8920 -0.2317 -0.9701 -0.0725
1.1795 0.0626 -11.5052 -0.8915 0.3156 0.3249
-1.1373 0.1510 11.5365 0.9041 -0.3198 -0.2835

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6940
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.546
_diffrn_reflns_theta_min         4.782
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    114.00 148.00   0.50    0.44    --  109.41  38.00 -60.00   68
  2  ω    152.00 178.00   0.50    0.44    --  109.41  38.00 -60.00   52
  3  ω     98.00 178.00   0.50    0.44    --  109.41  27.00-160.00  160
  4  ω     39.00 123.00   0.50    0.11    --   49.27  27.00-160.00  168
  5  ω    -31.00  25.00   0.50    0.11    --  -49.27  19.00 -30.00  112
  6  ω    -71.00 -18.00   0.50    0.44    --  -90.00  57.00 150.00  106
  7  ω    -71.00 -23.00   0.50    0.44    --  -90.00  57.00  30.00   96
  8  ω    -48.00 -22.00   0.50    0.44    --  -90.00  38.00   0.00   52
  9  ω    -61.00 -24.00   0.50    0.44    --  -90.00  57.00 -60.00   74
 10  ω    -47.00 -18.00   0.50    0.44    --  -90.00  38.00-120.00   58
 11  ω    -55.00 -24.00   0.50    0.44    --  -90.00  57.00-180.00   62
 12  ω    -38.00  24.00   0.50    0.11    --  -49.27  27.00-160.00  124
 13  ω    -44.00 -18.00   0.50    0.44    --  -90.00  38.00 -60.00   52
 14  ω    -45.00 -20.00   0.50    0.44    --  -90.00  38.00 120.00   50
 15  ω   -122.00 -38.00   0.50    0.11    --  -49.27 -27.00  37.00  168
 16  ω   -163.00 -78.00   0.50    0.44    --  -90.00 -27.00  37.00  170
 17  ω   -159.00 -91.00   0.50    0.44    --  -90.00 -99.00 120.00  136
 18  ω    -24.00  28.00   0.50    0.11    --   49.27 -27.00  37.00  104
 19  ω     37.00  96.00   0.50    0.44    --  109.41 -77.00 -90.00  118
 20  ω     70.00 105.00   0.50    0.44    --  109.41 -99.00-120.00   70
 21  ω     40.00  78.00   0.50    0.44    --  109.41-125.00  30.00   76
 22  ω    -24.00  21.00   0.50    0.11    --   49.27 -19.00 -90.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0302863000
_diffrn_orient_matrix_UB_12      0.0407875000
_diffrn_orient_matrix_UB_13      0.0808166000
_diffrn_orient_matrix_UB_21      0.2292468000
_diffrn_orient_matrix_UB_22      -0.0644539000
_diffrn_orient_matrix_UB_23      -0.0042782000
_diffrn_orient_matrix_UB_31      0.0743523000
_diffrn_orient_matrix_UB_32      0.1819312000
_diffrn_orient_matrix_UB_33      -0.0196302000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.606
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.840
_reflns_number_gt                1667
_reflns_number_total             1757
_reflns_odcompleteness_completeness 99.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 620 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.043
_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/[σ²(Fo²)+(0.0529P)²+0.0520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0786
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.03686(18) 1.05259(15) 0.48551(7) 0.0192(3) Uani 1 1 d . . . . .
O2 O 0.31410(17) 0.96439(16) 0.42129(6) 0.0187(3) Uani 1 1 d . . . . .
N1 N 0.1145(2) 0.39614(19) 0.48726(8) 0.0166(3) Uani 1 1 d . . . . .
C1 C 0.1361(3) 0.9415(2) 0.44841(8) 0.0149(3) Uani 1 1 d . . . . .
C3 C 0.1473(3) 0.6344(2) 0.39632(9) 0.0158(3) Uani 1 1 d . . . . .
C6 C 0.2794(3) 0.5666(2) 0.26626(9) 0.0190(4) Uani 1 1 d . . . . .
C4 C 0.0671(3) 0.4533(2) 0.41199(9) 0.0182(4) Uani 1 1 d . . . . .
C2 C 0.0275(3) 0.7685(2) 0.44021(9) 0.0168(4) Uani 1 1 d . . . . .
C5 C 0.1326(3) 0.6716(2) 0.31499(9) 0.0179(4) Uani 1 1 d . . . . .
C7 C 0.5113(3) 0.5926(3) 0.28587(11) 0.0259(4) Uani 1 1 d . . . . .
C8 C 0.2428(3) 0.6131(3) 0.18700(10) 0.0281(4) Uani 1 1 d . . . . .
H9 H 0.161(3) 0.795(3) 0.3088(11) 0.020(5) Uiso 1 1 d . . . . .
H11 H 0.249(3) 0.446(3) 0.2703(10) 0.014(5) Uiso 1 1 d . . . . .
H1 H 0.003(4) 0.730(3) 0.4903(13) 0.024(5) Uiso 1 1 d . . . . .
H14 H 0.544(4) 0.722(3) 0.2858(13) 0.032(6) Uiso 1 1 d . . . . .
H2 H -0.114(4) 0.789(3) 0.4202(12) 0.024(5) Uiso 1 1 d . . . . .
H3 H 0.298(3) 0.639(3) 0.4111(11) 0.021(5) Uiso 1 1 d . . . . .
H16 H 0.274(4) 0.729(3) 0.1810(14) 0.033(6) Uiso 1 1 d . . . . .
H5 H -0.084(3) 0.448(3) 0.4057(11) 0.022(5) Uiso 1 1 d . . . . .
H7 H 0.102(4) 0.276(3) 0.4887(12) 0.023(5) Uiso 1 1 d . . . . .
H6 H 0.249(4) 0.422(3) 0.4988(12) 0.027(6) Uiso 1 1 d . . . . .
H10 H -0.016(4) 0.654(3) 0.3001(11) 0.022(5) Uiso 1 1 d . . . . .
H4 H 0.139(4) 0.367(3) 0.3803(12) 0.025(5) Uiso 1 1 d . . . . .
H8 H 0.027(4) 0.445(3) 0.5200(13) 0.032(6) Uiso 1 1 d . . . . .
H13 H 0.551(4) 0.550(3) 0.3341(13) 0.029(6) Uiso 1 1 d . . . . .
H15 H 0.332(4) 0.542(4) 0.1530(14) 0.041(7) Uiso 1 1 d . . . . .
H17 H 0.095(5) 0.595(4) 0.1721(15) 0.045(7) Uiso 1 1 d . . . . .
H12 H 0.599(4) 0.544(4) 0.2485(13) 0.035(6) 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 1.272(2) . ?
O2 C1 1.249(2) . ?
N1 C4 1.493(2) . ?
N1 H7 0.95(2) . ?
N1 H6 0.90(3) . ?
N1 H8 0.91(3) . ?
C1 C2 1.524(2) . ?
C3 C4 1.530(2) . ?
C3 C2 1.528(2) . ?
C3 C5 1.535(2) . ?
C3 H3 0.99(2) . ?
C6 C5 1.534(2) . ?
C6 C7 1.529(3) . ?
C6 C8 1.528(3) . ?
C6 H11 0.97(2) . ?
C4 H5 0.97(2) . ?
C4 H4 1.00(2) . ?
C2 H1 0.99(2) . ?
C2 H2 0.98(2) . ?
C5 H9 0.99(2) . ?
C5 H10 0.99(2) . ?
C7 H14 1.03(3) . ?
C7 H13 0.99(2) . ?
C7 H12 0.96(3) . ?
C8 H16 0.93(3) . ?
C8 H15 1.01(3) . ?
C8 H17 0.99(3) . ?

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
C4 N1 H7 107.9(14) . . ?
C4 N1 H6 110.1(15) . . ?
C4 N1 H8 112.0(15) . . ?
H7 N1 H6 107(2) . . ?
H7 N1 H8 110(2) . . ?
H6 N1 H8 109(2) . . ?
O1 C1 C2 115.73(14) . . ?
O2 C1 O1 124.51(15) . . ?
O2 C1 C2 119.72(15) . . ?
C4 C3 C5 109.91(14) . . ?
C4 C3 H3 107.4(13) . . ?
C2 C3 C4 111.54(13) . . ?
C2 C3 C5 111.13(14) . . ?
C2 C3 H3 108.0(13) . . ?
C5 C3 H3 108.8(12) . . ?
C5 C6 H11 110.8(11) . . ?
C7 C6 C5 111.94(14) . . ?
C7 C6 H11 107.7(11) . . ?
C8 C6 C5 110.12(15) . . ?
C8 C6 C7 110.02(16) . . ?
C8 C6 H11 106.0(11) . . ?
N1 C4 C3 112.71(14) . . ?
N1 C4 H5 107.4(13) . . ?
N1 C4 H4 104.7(13) . . ?
C3 C4 H5 110.3(14) . . ?
C3 C4 H4 110.9(13) . . ?
H5 C4 H4 111(2) . . ?
C1 C2 C3 115.82(13) . . ?
C1 C2 H1 104.3(13) . . ?
C1 C2 H2 107.6(14) . . ?
C3 C2 H1 111.8(13) . . ?
C3 C2 H2 111.6(13) . . ?
H1 C2 H2 104.9(19) . . ?
C3 C5 H9 106.7(12) . . ?
C3 C5 H10 107.7(12) . . ?
C6 C5 C3 115.95(14) . . ?
C6 C5 H9 110.1(13) . . ?
C6 C5 H10 109.9(13) . . ?
H9 C5 H10 105.9(18) . . ?
C6 C7 H14 109.0(15) . . ?
C6 C7 H13 114.6(14) . . ?
C6 C7 H12 109.3(15) . . ?
H14 C7 H13 106(2) . . ?
H14 C7 H12 105(2) . . ?
H13 C7 H12 112(2) . . ?
C6 C8 H16 108.2(16) . . ?
C6 C8 H15 112.3(16) . . ?
C6 C8 H17 112.2(16) . . ?
H16 C8 H15 110(2) . . ?
H16 C8 H17 108(2) . . ?
H15 C8 H17 106(2) . . ?

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
O1 C1 C2 C3 -179.41(13) . . . . ?
O2 C1 C2 C3 -1.6(2) . . . . ?
C4 C3 C2 C1 160.76(14) . . . . ?
C4 C3 C5 C6 -67.03(18) . . . . ?
C2 C3 C4 N1 -67.26(17) . . . . ?
C2 C3 C5 C6 169.01(14) . . . . ?
C5 C3 C4 N1 169.01(13) . . . . ?
C5 C3 C2 C1 -76.21(17) . . . . ?
C7 C6 C5 C3 -59.0(2) . . . . ?
C8 C6 C5 C3 178.24(14) . . . . ?

_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 1.309
_oxdiff_exptl_absorpt_empirical_full_min 0.737
####################################################################### 
# 
# 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_R-Phenibut_S-Mandelic_Acid
_database_code_depnum_ccdc_archive 'CCDC 2170102'
loop_
_audit_author_name
_audit_author_address
'Daniel Komisarek'
;Heinrich Heine University Duesseldorf
Germany
;
_audit_update_record             
;
2022-05-03 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_name_common            '(R)-Phenibut (S)-Mandelic Acid'
_chemical_name_systematic        
'(R)-3-phenyl-Î³-aminobutyric acid (S)-2-Hydroxy-2-phenylacetic acid'
_chemical_formula_moiety         'C10 H13 N O2, C8 H8 O3'
_chemical_formula_sum            'C18 H21 N O5'
_chemical_formula_weight         331.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8H8O3 C10H13NO2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.1307(2)
_cell_length_b                   6.35390(10)
_cell_length_c                   13.0633(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.469(2)
_cell_angle_gamma                90
_cell_volume                     837.05(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12151
_cell_measurement_temperature    99.96(11)
_cell_measurement_theta_max      76.5310
_cell_measurement_theta_min      3.3430
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.683
_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_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -4 1 0.1413
-6 -1 2 0.1074
-4 3 1 0.2730
2 4 -2 0.2977
6 0 -2 0.2414
-3 -3 5 0.1391
0 0 8 0.0647
-1 0 -8 0.0319
-4 0 7 0.1091
-1 3 6 0.2163
4 0 -7 0.1804
0 -3 -5 0.1277
1 4 4 0.2738
5 0 5 0.1586
0 -3 6 0.1147
3 3 -3 0.2658
-5 -1 -5 0.0792
-2 0 8 0.0862
0 2 8 0.1484

_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.12
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0696 -4.1035 0.8769 0.1366 0.5859 0.7988
-6.2621 -0.9409 2.4681 -0.1452 -0.5996 0.7870
-3.7888 3.3696 0.6759 -0.2208 -0.9330 -0.2841
2.0003 3.8795 -1.5312 -0.0744 -0.3266 -0.9422
6.4297 0.3377 -2.4038 0.1703 0.7066 -0.6868
-3.3905 -2.9060 4.5325 -0.3083 0.0689 0.9488
0.4001 -0.2280 8.3637 -0.9547 0.2261 0.1938
-0.7527 -0.0485 -8.2930 0.9672 -0.2294 -0.1088
-4.2831 -0.0326 6.9273 -0.7374 -0.4059 0.5399
-1.1034 2.9463 5.8710 -0.8305 -0.4512 -0.3266
4.2848 0.0360 -6.9255 0.7370 0.4057 -0.5406
-0.1289 -3.4607 -4.5764 0.7278 0.3937 0.5615
0.6711 3.6123 3.9035 -0.6664 -0.3596 -0.6531
4.6879 0.1809 5.3327 -0.6874 0.6467 -0.3307
-0.1088 -2.9011 6.0135 -0.5233 0.4999 0.6901
3.2189 3.3368 -3.1443 0.1260 -0.1270 -0.9839
-4.9473 -0.5670 -4.8310 0.6554 -0.6156 0.4376
-2.3581 0.1619 8.1609 -0.9165 -0.1739 0.3602
-0.4540 1.8215 7.6068 -0.9742 -0.1821 -0.1336

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00  56.00   0.50    0.11    --   47.52  77.00 -30.00   60
  2  ω     41.00  67.00   0.50    0.11    --   62.00  76.00-130.76   52
  3  ω     42.00  69.00   0.50    0.11    --   62.00  73.00  82.12   54
  4  ω     44.00  70.00   0.50    0.11    --   62.00  70.00  71.08   52
  5  ω     38.00  87.00   0.50    0.11    --   58.00  72.00 121.00   98
  6  ω     51.00  78.00   0.50    0.11    --   47.52  19.00 120.00   54
  7  ω     81.00 107.00   0.50    0.44    --  110.04-113.00 -54.00   52
  8  ω     41.00 104.00   0.50    0.44    --  110.04 -99.00 -30.00  126
  9  ω     41.00  79.00   0.50    0.44    --  110.04-113.00 -54.00   76
 10  ω     39.00  65.00   0.50    0.44    --  110.04 -99.00  30.00   52
 11  ω     74.00 100.00   0.50    0.44    --  110.04 -99.00  30.00   52
 12  ω     70.00 106.00   0.50    0.44    --  110.04 -99.00  90.00   72
 13  ω     40.00  90.00   0.50    0.44    --  110.04 -99.00 150.00  100
 14  ω     40.00  66.00   0.50    0.44    --  110.04 -99.00  90.00   52
 15  ω     48.00 106.00   0.50    0.44    --  110.04 -99.00-120.00  116
 16  ω     42.00 106.00   0.50    0.44    --  110.04 -99.00-180.00  128
 17  ω     63.00  90.00   0.50    0.44    --  110.04 -99.00   0.00   54
 18  ω     39.00  99.00   0.50    0.44    --  110.04 -77.00  30.00  120
 19  ω     63.00 119.00   0.50    0.11    --   47.52-178.00  90.00  112
 20  ω     42.00  83.00   0.50    0.11    --   47.52-113.00 -54.00   82
 21  ω    108.00 141.00   0.50    0.44    --  110.04 113.00  37.00   66
 22  ω    -61.00 -18.00   0.50    0.44    --  -90.00 125.00  60.00   86
 23  ω    -74.00 -49.00   0.50    0.44    --  -90.00 113.00  37.00   50
 24  ω    -48.00  -7.00   0.50    0.11    --  -47.52 113.00  37.00   82
 25  ω    -68.00 -21.00   0.50    0.44    --  -90.00  57.00   0.00   94
 26  ω    -53.00 -19.00   0.50    0.44    --  -90.00  57.00 -90.00   68
 27  ω    -68.00 -37.00   0.50    0.44    --  -90.00  57.00-120.00   62
 28  ω    -45.00 -18.00   0.50    0.44    --  -90.00  38.00-120.00   54
 29  ω   -156.00-111.00   0.50    0.44    --  -90.00 -52.00 -14.84   90
 30  ω   -129.00-102.00   0.50    0.11    --  -58.00 -77.00 -96.31   54
 31  ω    -93.00 -48.00   0.50    0.44    --  -70.00 -77.00 -84.35   90
 32  ω    -64.00 -37.00   0.50    0.11    --  -58.00 -77.00 -96.31   54
 33  ω   -107.00 -69.00   0.50    0.44    --  -90.00 -77.00-180.00   76
 34  ω   -111.00 -69.00   0.50    0.44    --  -90.00 -77.00-150.00   84
 35  ω   -152.00-121.00   0.50    0.44    --  -90.00 -77.00-150.00   62
 36  ω   -149.00-110.00   0.50    0.44    --  -90.00 -77.00 -30.00   78
 37  ω   -158.00-126.00   0.50    0.44    --  -90.00 -77.00   0.00   64
 38  ω   -120.00 -68.00   0.50    0.44    --  -90.00 -77.00   0.00  104
 39  ω   -107.00 -69.00   0.50    0.44    --  -90.00 -77.00 -30.00   76
 40  ω   -105.00 -72.00   0.50    0.44    --  -90.00 -77.00  30.00   66
 41  ω    -99.00 -70.00   0.50    0.44    --  -90.00 -76.00  45.55   58
 42  ω    -87.00 -61.00   0.50    0.44    --  -82.00 -76.00 156.28   52
 43  ω   -150.00-124.00   0.50    0.44    --  -82.00 -76.00 156.28   52
 44  ω    -78.00 -53.00   0.50    0.44    --  -74.00 -75.00 145.99   50
 45  ω   -155.00-120.00   0.50    0.44    --  -90.00 -77.00  30.00   70
 46  ω   -156.00-104.00   0.50    0.44    --  -90.00 -76.00  45.55  104
 47  ω   -136.00-110.00   0.50    0.44    --  -74.00 -75.00 145.99   52
 48  ω    -82.00 -57.00   0.50    0.44    --  -78.00 -74.00 114.61   50
 49  ω    -87.00 -61.00   0.50    0.44    --  -82.00 -75.00  44.84   52
 50  ω    -96.00 -61.00   0.50    0.44    --  -82.00 -74.00  74.73   70
 51  ω    -93.00 -44.00   0.50    0.11    --  -62.00 -73.00 171.95   98
 52  ω   -102.00 -77.00   0.50    0.44    --  -90.00 -73.00 153.25   50
 53  ω   -161.00-107.00   0.50    0.44    --  -90.00 -73.00 153.25  108
 54  ω   -160.00 -70.00   0.50    0.44    --  -90.00 -72.00  91.50  180
 55  ω    -93.00 -62.00   0.50    0.44    --  -82.00 -72.00  57.89   62
 56  ω    -61.00 -35.00   0.50    0.11    --  -54.00 -75.00 -36.76   52
 57  ω    -77.00 -51.00   0.50    0.44    --  -70.00 -72.00 -36.45   52
 58  ω    -91.00 -65.00   0.50    0.44    --  -86.00 -76.00-121.38   52
 59  ω    -86.00 -59.00   0.50    0.44    --  -78.00 -73.00-112.42   54
 60  ω    -84.00 -58.00   0.50    0.44    --  -78.00 -72.00 -61.94   52
 61  ω   -145.00-107.00   0.50    0.44    --  -82.00 -68.00-156.86   76
 62  ω    -93.00 -64.00   0.50    0.44    --  -82.00 -68.00-156.86   58
 63  ω    -85.00 -57.00   0.50    0.44    --  -74.00 -67.00-158.02   56
 64  ω    -83.00 -56.00   0.50    0.44    --  -74.00 -67.00-118.93   54
 65  ω   -106.00 -63.00   0.50    0.44    --  -78.00 -70.00 -27.62   86
 66  ω    -87.00 -54.00   0.50    0.44    --  -70.00 -66.00-151.42   66
 67  ω    -77.00 -52.00   0.50    0.44    --  -70.00 -69.00 -10.19   50
 68  ω   -101.00 -61.00   0.50    0.44    --  -78.00 -66.00  -6.57   80
 69  ω   -144.00-106.00   0.50    0.44    --  -78.00 -65.00-104.12   76
 70  ω   -161.00-127.00   0.50    0.44    --  -90.00 -65.00 -64.24   68
 71  ω   -116.00 -74.00   0.50    0.44    --  -90.00 -65.00 -64.24   84
 72  ω    -86.00 -61.00   0.50    0.44    --  -78.00 -65.00-104.12   50
 73  ω   -160.00-127.00   0.50    0.44    --  -90.00 -60.00-102.81   66
 74  ω   -157.00-124.00   0.50    0.44    --  -90.00 -60.00-126.74   66
 75  ω   -113.00 -76.00   0.50    0.44    --  -90.00 -60.00-126.74   74
 76  ω   -108.00 -83.00   0.50    0.44    --  -90.00 -60.00-102.81   50
 77  ω   -154.00 -85.00   0.50    0.44    --  -90.00 -57.00-180.00  138
 78  ω    -74.00 -48.00   0.50    0.11    --  -66.00 -67.00   3.88   52
 79  ω    -99.00 -72.00   0.50    0.44    --  -90.00 -67.00 116.46   54
 80  ω    -85.00 -59.00   0.50    0.44    --  -78.00 -69.00 169.93   52
 81  ω   -128.00 -77.00   0.50    0.44    --  -90.00 -56.00 110.53  102
 82  ω   -128.00 -94.00   0.50    0.44    --  -90.00 -57.00  60.00   68
 83  ω   -127.00 -95.00   0.50    0.44    --  -90.00-113.00 -54.00   64
 84  ω   -112.00 -84.00   0.50    0.11    --  -47.52 -77.00  60.00   56
 85  ω    -63.00 -27.00   0.50    0.11    --  -47.52 -77.00  60.00   72
 86  ω    -72.00 -37.00   0.50    0.11    --  -47.52 -38.00  60.00   70
 87  ω    -52.00 -26.00   0.50    0.11    --  -47.52 -77.00   0.00   52
 88  ω    -75.00 -45.00   0.50    0.11    --  -47.52 -38.00 -30.00   60
 89  ω   -101.00 -75.00   0.50    0.11    --  -47.52 -77.00-180.00   52
 90  ω    -52.00 -26.00   0.50    0.11    --  -47.52 -77.00-180.00   52
 91  ω     12.00  37.00   0.50    0.11    --   30.00  83.00-140.75   50
 92  ω     13.00  43.00   0.50    0.11    --   38.00  86.00 -70.55   60
 93  ω     69.00 116.00   0.50    0.11    --   47.52 178.00 -60.00   94
 94  ω     -6.00  19.00   0.50    0.11    --   26.00  99.00 107.04   50
 95  ω    -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       'ω 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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_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_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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_coef       .
_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_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.068
_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/[σ²(Fo²)+(0.0431P)²+0.1753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0824
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O2B O -0.02218(14) 0.4224(3) 0.50220(12) 0.0231(3) Uani 1 1 d . . . . .
O1B O 0.14424(14) 0.3568(3) 0.40501(12) 0.0237(4) Uani 1 1 d . . . . .
O2A O 0.44582(14) 0.2274(3) 0.53110(12) 0.0244(4) Uani 1 1 d . . . . .
O3B O -0.20568(14) 0.3030(3) 0.34106(12) 0.0257(4) Uani 1 1 d . . . . .
O1A O 0.29938(14) 0.4815(3) 0.55328(12) 0.0236(3) Uani 1 1 d . . . . .
N1A N 0.71507(18) 0.4002(3) 0.55306(14) 0.0205(4) Uani 1 1 d . . . . .
C3B C -0.0623(2) 0.5112(4) 0.24958(16) 0.0204(4) Uani 1 1 d . . . . .
C1B C 0.0180(2) 0.3731(4) 0.42089(16) 0.0203(4) Uani 1 1 d . . . . .
C8B C -0.1448(2) 0.6844(4) 0.25710(17) 0.0238(5) Uani 1 1 d . . . . .
C1A C 0.40657(19) 0.3795(4) 0.57941(16) 0.0203(4) Uani 1 1 d . . . . .
C10A C 0.6045(2) 0.1438(4) 0.88631(18) 0.0259(5) Uani 1 1 d . . . . .
C5A C 0.6317(2) 0.3238(4) 0.83117(16) 0.0217(4) Uani 1 1 d . . . . .
C4A C 0.7329(2) 0.3930(4) 0.66746(16) 0.0222(5) Uani 1 1 d . . . . .
C3A C 0.6073(2) 0.3243(4) 0.71439(16) 0.0218(4) Uani 1 1 d . . . . .
C2B C -0.0715(2) 0.3272(4) 0.32223(16) 0.0210(4) Uani 1 1 d . . . . .
C2A C 0.4850(2) 0.4568(4) 0.67776(17) 0.0228(5) Uani 1 1 d . . . . .
C6A C 0.6793(2) 0.5015(4) 0.88636(18) 0.0248(5) Uani 1 1 d . . . . .
C9A C 0.6260(2) 0.1396(4) 0.99305(19) 0.0287(5) Uani 1 1 d . . . . .
C4B C 0.0297(2) 0.5128(4) 0.17671(17) 0.0257(5) Uani 1 1 d . . . . .
C5B C 0.0404(2) 0.6878(5) 0.11409(18) 0.0302(6) Uani 1 1 d . . . . .
C8A C 0.6756(2) 0.3148(4) 1.04655(18) 0.0279(5) Uani 1 1 d . . . . .
C7A C 0.7015(2) 0.4964(4) 0.99257(18) 0.0277(5) Uani 1 1 d . . . . .
C6B C -0.0417(2) 0.8605(4) 0.12276(18) 0.0306(5) Uani 1 1 d . . . . .
C7B C -0.1351(2) 0.8575(4) 0.19370(18) 0.0283(5) Uani 1 1 d . . . . .
H6A H 0.676(3) 0.282(5) 0.528(2) 0.023(7) Uiso 1 1 d . . . . .
H9A H 0.697(3) 0.634(5) 0.851(2) 0.024(7) Uiso 1 1 d . . . . .
H4A H 0.811(3) 0.298(5) 0.688(2) 0.027(7) Uiso 1 1 d . . . . .
H4B H 0.089(3) 0.385(6) 0.171(2) 0.035(7) Uiso 1 1 d . . . . .
H7A H 0.793(3) 0.416(5) 0.524(2) 0.030(7) Uiso 1 1 d . . . . .
H11A H 0.692(2) 0.311(4) 1.123(2) 0.022(6) Uiso 1 1 d . . . . .
H8B H -0.209(3) 0.680(5) 0.308(2) 0.025(7) Uiso 1 1 d . . . . .
H7B H -0.191(3) 0.976(5) 0.200(2) 0.029(7) Uiso 1 1 d . . . . .
H13A H 0.572(3) 0.011(6) 0.847(2) 0.038(8) Uiso 1 1 d . . . . .
H5A H 0.759(3) 0.535(5) 0.689(2) 0.027(7) Uiso 1 1 d . . . . .
H12A H 0.608(3) 0.012(5) 1.027(2) 0.033(7) Uiso 1 1 d . . . . .
H2B H -0.040(3) 0.198(5) 0.291(2) 0.025(7) Uiso 1 1 d . . . . .
H5B H 0.106(3) 0.695(5) 0.063(2) 0.038(8) Uiso 1 1 d . . . . .
H1A H 0.420(2) 0.460(4) 0.7326(19) 0.021(6) Uiso 1 1 d . . . . .
H3A H 0.587(3) 0.169(5) 0.691(2) 0.025(7) Uiso 1 1 d . . . . .
H8A H 0.661(3) 0.517(6) 0.525(2) 0.037(8) Uiso 1 1 d . . . . .
H2A H 0.505(3) 0.606(5) 0.667(2) 0.025(7) Uiso 1 1 d . . . . .
H10A H 0.734(3) 0.618(5) 1.028(2) 0.031(7) Uiso 1 1 d . . . . .
H6B H -0.037(3) 0.986(5) 0.078(2) 0.038(8) Uiso 1 1 d . . . . .
H3B H -0.223(3) 0.176(6) 0.376(2) 0.044(9) Uiso 1 1 d . . . . .
H1B H 0.202(4) 0.405(7) 0.466(3) 0.068(11) 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
O2B C1B 1.214(3) . ?
O1B C1B 1.319(2) . ?
O1B H1B 1.00(4) . ?
O2A C1A 1.240(3) . ?
O3B C2B 1.413(2) . ?
O3B H3B 0.95(4) . ?
O1A C1A 1.283(3) . ?
N1A C4A 1.489(3) . ?
N1A H6A 0.90(3) . ?
N1A H7A 0.92(3) . ?
N1A H8A 0.97(4) . ?
C3B C8B 1.391(3) . ?
C3B C2B 1.514(3) . ?
C3B C4B 1.395(3) . ?
C1B C2B 1.532(3) . ?
C8B C7B 1.386(3) . ?
C8B H8B 0.97(3) . ?
C1A C2A 1.526(3) . ?
C10A C5A 1.393(3) . ?
C10A C9A 1.391(3) . ?
C10A H13A 1.02(4) . ?
C5A C3A 1.522(3) . ?
C5A C6A 1.400(3) . ?
C4A C3A 1.528(3) . ?
C4A H4A 1.01(3) . ?
C4A H5A 0.97(3) . ?
C3A C2A 1.537(3) . ?
C3A H3A 1.05(3) . ?
C2B H2B 0.99(3) . ?
C2A H1A 1.02(3) . ?
C2A H2A 0.98(3) . ?
C6A C7A 1.385(3) . ?
C6A H9A 0.99(3) . ?
C9A C8A 1.383(4) . ?
C9A H12A 0.95(3) . ?
C4B C5B 1.391(4) . ?
C4B H4B 1.01(3) . ?
C5B C6B 1.387(4) . ?
C5B H5B 0.99(3) . ?
C8A C7A 1.390(4) . ?
C8A H11A 1.00(2) . ?
C7A H10A 0.94(3) . ?
C6B C7B 1.387(4) . ?
C6B H6B 0.99(3) . ?
C7B H7B 0.95(3) . ?

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
C1B O1B H1B 111(2) . . ?
C2B O3B H3B 113(2) . . ?
C4A N1A H6A 110.2(18) . . ?
C4A N1A H7A 113.3(17) . . ?
C4A N1A H8A 114.2(18) . . ?
H6A N1A H7A 108(3) . . ?
H6A N1A H8A 107(2) . . ?
H7A N1A H8A 104(3) . . ?
C8B C3B C2B 119.55(19) . . ?
C8B C3B C4B 119.2(2) . . ?
C4B C3B C2B 121.2(2) . . ?
O2B C1B O1B 124.66(19) . . ?
O2B C1B C2B 124.35(18) . . ?
O1B C1B C2B 110.97(17) . . ?
C3B C8B H8B 118.1(18) . . ?
C7B C8B C3B 120.5(2) . . ?
C7B C8B H8B 121.3(18) . . ?
O2A C1A O1A 124.24(19) . . ?
O2A C1A C2A 120.85(19) . . ?
O1A C1A C2A 114.91(19) . . ?
C5A C10A H13A 119.2(17) . . ?
C9A C10A C5A 120.9(2) . . ?
C9A C10A H13A 119.8(18) . . ?
C10A C5A C3A 119.9(2) . . ?
C10A C5A C6A 118.1(2) . . ?
C6A C5A C3A 122.0(2) . . ?
N1A C4A C3A 112.66(17) . . ?
N1A C4A H4A 107.8(14) . . ?
N1A C4A H5A 105.5(16) . . ?
C3A C4A H4A 112.4(15) . . ?
C3A C4A H5A 111.0(17) . . ?
H4A C4A H5A 107(2) . . ?
C5A C3A C4A 109.92(16) . . ?
C5A C3A C2A 111.24(18) . . ?
C5A C3A H3A 107.2(15) . . ?
C4A C3A C2A 113.34(19) . . ?
C4A C3A H3A 107.6(15) . . ?
C2A C3A H3A 107.3(15) . . ?
O3B C2B C3B 108.13(17) . . ?
O3B C2B C1B 112.12(17) . . ?
O3B C2B H2B 109.4(16) . . ?
C3B C2B C1B 108.26(17) . . ?
C3B C2B H2B 110.0(16) . . ?
C1B C2B H2B 108.9(16) . . ?
C1A C2A C3A 115.19(19) . . ?
C1A C2A H1A 106.4(14) . . ?
C1A C2A H2A 106.6(16) . . ?
C3A C2A H1A 110.4(14) . . ?
C3A C2A H2A 113.6(16) . . ?
H1A C2A H2A 104(2) . . ?
C5A C6A H9A 120.9(15) . . ?
C7A C6A C5A 120.8(2) . . ?
C7A C6A H9A 118.3(16) . . ?
C10A C9A H12A 117.7(18) . . ?
C8A C9A C10A 120.4(2) . . ?
C8A C9A H12A 121.9(18) . . ?
C3B C4B H4B 118.4(17) . . ?
C5B C4B C3B 120.1(2) . . ?
C5B C4B H4B 121.5(17) . . ?
C4B C5B H5B 122(2) . . ?
C6B C5B C4B 120.3(2) . . ?
C6B C5B H5B 118(2) . . ?
C9A C8A C7A 119.2(2) . . ?
C9A C8A H11A 120.3(16) . . ?
C7A C8A H11A 120.5(16) . . ?
C6A C7A C8A 120.5(2) . . ?
C6A C7A H10A 119.1(18) . . ?
C8A C7A H10A 120.4(18) . . ?
C5B C6B H6B 121.7(18) . . ?
C7B C6B C5B 119.7(2) . . ?
C7B C6B H6B 118.5(18) . . ?
C8B C7B C6B 120.1(2) . . ?
C8B C7B H7B 120.0(17) . . ?
C6B C7B H7B 119.9(17) . . ?

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
O2B C1B C2B O3B -13.0(3) . . . . ?
O2B C1B C2B C3B 106.2(2) . . . . ?
O1B C1B C2B O3B 168.43(18) . . . . ?
O1B C1B C2B C3B -72.4(2) . . . . ?
O2A C1A C2A C3A -4.0(3) . . . . ?
O1A C1A C2A C3A 175.18(19) . . . . ?
N1A C4A C3A C5A -179.09(19) . . . . ?
N1A C4A C3A C2A -53.9(3) . . . . ?
C3B C8B C7B C6B -0.7(3) . . . . ?
C3B C4B C5B C6B -0.9(3) . . . . ?
C8B C3B C2B O3B 35.4(3) . . . . ?
C8B C3B C2B C1B -86.3(2) . . . . ?
C8B C3B C4B C5B 1.4(3) . . . . ?
C10A C5A C3A C4A -126.6(2) . . . . ?
C10A C5A C3A C2A 107.0(2) . . . . ?
C10A C5A C6A C7A 1.5(3) . . . . ?
C10A C9A C8A C7A 1.0(3) . . . . ?
C5A C10A C9A C8A -0.2(3) . . . . ?
C5A C3A C2A C1A -147.46(19) . . . . ?
C5A C6A C7A C8A -0.6(3) . . . . ?
C4A C3A C2A C1A 88.1(2) . . . . ?
C3A C5A C6A C7A -179.6(2) . . . . ?
C2B C3B C8B C7B 177.86(19) . . . . ?
C2B C3B C4B C5B -177.03(19) . . . . ?
C6A C5A C3A C4A 54.5(3) . . . . ?
C6A C5A C3A C2A -71.9(3) . . . . ?
C9A C10A C5A C3A 180.0(2) . . . . ?
C9A C10A C5A C6A -1.1(3) . . . . ?
C9A C8A C7A C6A -0.6(3) . . . . ?
C4B C3B C8B C7B -0.6(3) . . . . ?
C4B C3B C2B O3B -146.2(2) . . . . ?
C4B C3B C2B C1B 92.1(2) . . . . ?
C4B C5B C6B C7B -0.5(3) . . . . ?
C5B C6B C7B C8B 1.3(3) . . . . ?

_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
####################################################################### 
# 
# 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_R-PGB_S-MAN
_database_code_depnum_ccdc_archive 'CCDC 2170101'
loop_
_audit_author_name
_audit_author_address
'Daniel Komisarek'
;Heinrich Heine University Duesseldorf
Germany
;
_audit_update_record             
;
2022-05-03 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_name_common            '(R)-Pregabalin (S)-Mandelic Acid'
_chemical_name_systematic        
'(R)-3-isobutyl-Î³-aminobutyric acid (S)-2-Hydroxy-2-phenylacetic acid'
_chemical_formula_moiety         'C8 H18 N O2, C8 H7 N O2'
_chemical_formula_sum            'C16 H25 N O5'
_chemical_formula_weight         311.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8H18NO2 C8H7O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.05170(10)
_cell_length_b                   29.8989(5)
_cell_length_c                   9.30690(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.6410(10)
_cell_angle_gamma                90
_cell_volume                     1682.19(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17743
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7720
_cell_measurement_theta_min      2.9390
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.801
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.580
_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_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -19 1 0.0430
-3 12 -1 0.0430
0 19 -1 0.0436
2 16 0 0.1309
4 -2 1 0.2315
0 16 3 0.0369
-2 0 6 0.0479
-1 -18 0 0.0472
1 -4 -6 0.0709
0 -5 6 0.0419
1 7 6 0.0666

_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.3183 -19.1034 0.9794 -0.2316 0.1819 -0.9556
-2.9617 11.8661 -1.2559 0.7539 -0.5782 0.3119
0.1611 19.1288 -1.0130 0.2624 -0.2053 0.9429
2.1087 16.3362 -0.4612 -0.1565 0.1149 0.9810
3.8349 -1.9183 0.8909 -0.7699 0.5877 0.2488
0.0196 16.0126 3.4055 0.5339 0.4537 0.7135
-1.7048 0.3751 5.5557 0.7395 0.6346 -0.2245
-1.1956 -18.4673 -0.1607 -0.1157 -0.0940 -0.9888
1.4458 -4.2202 -5.5569 -0.7593 -0.6505 0.0172
-0.4626 -4.8760 5.8313 0.4009 0.8405 -0.3645
0.5018 7.0725 5.5285 0.4085 0.8624 0.2991

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_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            25468
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.135
_diffrn_reflns_theta_min         2.956
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 -22.00   0.50    0.17    --  -90.00  57.00  30.00   76
  2  ω    -61.00 -35.00   0.50    0.17    --  -90.00  57.00 -30.00   52
  3  ω     53.00  86.00   0.50    0.05    --   49.27  38.00 -30.00   66
  4  ω     99.00 135.00   0.50    0.17    --  109.41  29.00-110.00   72
  5  ω     76.00 106.00   0.50    0.05    --   49.27  29.00-110.00   60
  6  ω    -62.00 -36.00   0.50    0.17    --  -90.00  57.00  60.00   52
  7  ω    -69.00 -19.00   0.50    0.17    --  -90.00  57.00   0.00  100
  8  ω    -48.00 -19.00   0.50    0.17    --  -90.00  38.00 -30.00   58
  9  ω    -71.00 -46.00   0.50    0.17    --  -90.00  57.00 -90.00   50
 10  ω    -43.00 -18.00   0.50    0.17    --  -90.00  38.00 -90.00   50
 11  ω    -48.00 -19.00   0.50    0.17    --  -90.00  38.00-180.00   58
 12  ω    -75.00 -21.00   0.50    0.17    --  -90.00 125.00 -30.00  108
 13  ω    -80.00 -36.00   0.50    0.17    --  -90.00 125.00 150.00   88
 14  ω    -75.00 -38.00   0.50    0.05    --  -49.27 -19.00 -30.00   74
 15  ω   -119.00 -28.00   0.50    0.05    --  -49.27 -77.00 -30.00  182
 16  ω    -86.00 -29.00   0.50    0.05    --  -49.27 -77.00  30.00  114
 17  ω   -104.00 -79.00   0.50    0.05    --  -49.27 -29.00  88.00   50
 18  ω   -124.00 -72.00   0.50    0.17    --  -90.00 -77.00  60.00  104
 19  ω    -97.00 -72.00   0.50    0.17    --  -90.00 -75.00  26.07   50
 20  ω    -94.00 -68.00   0.50    0.17    --  -90.00 -77.00  30.00   52
 21  ω    -94.00 -69.00   0.50    0.17    --  -90.00 -77.00   0.00   50
 22  ω    -95.00 -70.00   0.50    0.17    --  -90.00 -77.00 -30.00   50
 23  ω    -97.00 -71.00   0.50    0.17    --  -90.00 -72.00 -43.62   52
 24  ω   -122.00 -69.00   0.50    0.17    --  -90.00 -75.00 -13.02  106
 25  ω   -143.00-117.00   0.50    0.17    --  -90.00 -72.00 -43.62   52
 26  ω   -161.00-104.00   0.50    0.17    --  -90.00 -72.00 -76.74  114
 27  ω    -97.00 -72.00   0.50    0.17    --  -90.00 -71.00  -1.58   50
 28  ω   -115.00 -71.00   0.50    0.17    --  -90.00 -71.00  13.02   88
 29  ω   -160.00-127.00   0.50    0.17    --  -90.00 -75.00  26.07   66
 30  ω   -156.00-113.00   0.50    0.17    --  -90.00 -74.00  46.81   86
 31  ω    -94.00 -69.00   0.50    0.17    --  -90.00 -74.00  44.12   50
 32  ω   -114.00 -73.00   0.50    0.17    --  -90.00 -66.00  22.34   82
 33  ω   -118.00 -73.00   0.50    0.17    --  -90.00 -66.00  -7.31   90
 34  ω    -96.00 -71.00   0.50    0.17    --  -90.00 -69.00   5.01   50
 35  ω    -98.00 -73.00   0.50    0.17    --  -90.00 -64.00  -5.51   50
 36  ω    -96.00 -71.00   0.50    0.17    --  -90.00 -71.00 -36.09   50
 37  ω    -98.00 -73.00   0.50    0.17    --  -90.00 -65.00 -58.30   50
 38  ω    -99.00 -74.00   0.50    0.17    --  -90.00 -64.00 -65.61   50
 39  ω   -161.00 -75.00   0.50    0.17    --  -90.00 -68.00 -65.17  172
 40  ω   -161.00-135.00   0.50    0.17    --  -90.00 -64.00  -5.51   52
 41  ω   -121.00 -90.00   0.50    0.17    --  -90.00 -29.00  88.00   62
 42  ω   -155.00-115.00   0.50    0.17    --  -90.00 -63.00 -39.71   80
 43  ω   -110.00 -74.00   0.50    0.17    --  -90.00 -63.00 -39.71   72
 44  ω   -128.00 -81.00   0.50    0.17    --  -90.00 -38.00-180.00   94
 45  ω   -158.00-133.00   0.50    0.17    --  -90.00 -38.00-180.00   50
 46  ω   -116.00 -77.00   0.50    0.05    --  -49.27-125.00-150.00   78
 47  ω    -24.00   2.00   0.50    0.05    --   49.27 -19.00 -60.00   52
 48  ω    -18.00  18.00   0.50    0.05    --   49.27 -19.00 -30.00   72
 49  ω     74.00  99.00   0.50    0.17    --  109.41 -77.00 -60.00   50
 50  ω     39.00  89.00   0.50    0.17    --  109.41 -77.00  90.00  100
 51  ω     -9.00  24.00   0.50    0.05    --   49.27 -29.00  88.00   66
 52  ω     70.00 102.00   0.50    0.17    --  109.41 -99.00 -60.00   64
 53  ω     43.00 101.00   0.50    0.17    --  109.41-125.00  90.00  116
 54  ω    -38.00  22.00   0.50    0.05    --  -49.27  29.00-110.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2070703000
_diffrn_orient_matrix_UB_12      0.0190762000
_diffrn_orient_matrix_UB_13      0.0682755000
_diffrn_orient_matrix_UB_21      0.1164700000
_diffrn_orient_matrix_UB_22      -0.0037598000
_diffrn_orient_matrix_UB_23      0.1502268000
_diffrn_orient_matrix_UB_31      0.0923052000
_diffrn_orient_matrix_UB_32      0.0477024000
_diffrn_orient_matrix_UB_33      -0.0153049000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.853
_reflns_number_gt                6172
_reflns_number_total             6336
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 2806 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.15(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         6336
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.048
_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/[σ²(Fo²)+(0.0358P)²+0.2370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0733
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1C O 0.1523(2) 0.55553(5) 0.75655(14) 0.0193(3) Uani 1 1 d . . . . .
O1A O 0.1990(2) 0.47689(5) 0.64575(16) 0.0218(3) Uani 1 1 d . . . . .
O1D O 0.7339(2) 0.46231(5) 0.09777(15) 0.0225(3) Uani 1 1 d . . . . .
O2D O 0.9964(2) 0.47570(5) -0.05920(16) 0.0228(3) Uani 1 1 d . . . . .
O1B O 0.9133(3) 0.50793(5) 0.30613(17) 0.0237(3) Uani 1 1 d . . . . .
O2C O 0.4464(2) 0.55030(5) 0.91016(15) 0.0216(3) Uani 1 1 d . . . . .
O2A O 0.4090(2) 0.49913(5) 0.46700(15) 0.0216(3) Uani 1 1 d . . . . .
O3D O 0.7419(3) 0.45251(5) -0.28610(15) 0.0224(3) Uani 1 1 d . . . . .
O3C O 0.2373(3) 0.58208(6) 1.13131(15) 0.0249(3) Uani 1 1 d . . . . .
O2B O 0.6827(3) 0.56310(6) 0.23633(18) 0.0345(4) Uani 1 1 d . . . . .
N1B N 0.7014(3) 0.55192(6) 0.67216(19) 0.0194(3) Uani 1 1 d . . . . .
N1A N 0.3069(3) 0.47618(6) 0.17072(19) 0.0208(4) Uani 1 1 d . . . . .
C1D C 0.8093(3) 0.46286(7) -0.0280(2) 0.0187(4) Uani 1 1 d . . . . .
C1C C 0.2503(3) 0.56104(7) 0.8784(2) 0.0173(4) Uani 1 1 d . . . . .
C3D C 0.6074(4) 0.39549(7) -0.1269(2) 0.0209(4) Uani 1 1 d . . . . .
C1B C 0.8348(4) 0.54946(8) 0.3134(2) 0.0225(4) Uani 1 1 d . . . . .
C1A C 0.3054(3) 0.47005(7) 0.5265(2) 0.0183(4) Uani 1 1 d . . . . .
C3C C 0.0683(3) 0.63150(7) 0.9493(2) 0.0195(4) Uani 1 1 d . . . . .
C3A C 0.3903(4) 0.40999(7) 0.3367(2) 0.0202(4) Uani 1 1 d . . . . .
C4D C 0.3962(4) 0.37851(8) -0.1563(2) 0.0237(5) Uani 1 1 d . . . . .
C3B C 0.8271(4) 0.61189(7) 0.5063(2) 0.0213(4) Uani 1 1 d . . . . .
C2D C 0.6535(4) 0.44487(7) -0.1483(2) 0.0192(4) Uani 1 1 d . . . . .
C4C C -0.1433(4) 0.64346(8) 0.8973(2) 0.0232(4) Uani 1 1 d . . . . .
C2C C 0.1189(3) 0.58385(7) 0.9961(2) 0.0192(4) Uani 1 1 d . . . . .
C8C C 0.2347(4) 0.66357(8) 0.9516(3) 0.0266(5) Uani 1 1 d . . . . .
C2A C 0.2873(4) 0.42209(8) 0.4785(2) 0.0234(4) Uani 1 1 d . . . . .
C2B C 0.9612(3) 0.57720(7) 0.4245(2) 0.0203(4) Uani 1 1 d . . . . .
C5C C -0.1850(4) 0.68619(8) 0.8444(3) 0.0294(5) Uani 1 1 d . . . . .
C6A C 0.5103(4) 0.33132(8) 0.4382(3) 0.0295(5) Uani 1 1 d . . . . .
C4B C 0.6306(3) 0.59073(7) 0.5790(2) 0.0202(4) Uani 1 1 d . . . . .
C8D C 0.7756(4) 0.36631(8) -0.0815(3) 0.0295(5) Uani 1 1 d . . . . .
C5B C 0.7397(4) 0.65126(8) 0.4143(2) 0.0253(5) Uani 1 1 d . . . . .
C4A C 0.2595(4) 0.42857(8) 0.2054(2) 0.0238(4) Uani 1 1 d . . . . .
C5A C 0.3964(4) 0.35884(8) 0.3175(2) 0.0252(5) Uani 1 1 d . . . . .
C7D C 0.7340(4) 0.32091(8) -0.0680(3) 0.0348(6) Uani 1 1 d . . . . .
C6C C -0.0170(4) 0.71772(8) 0.8447(3) 0.0317(5) Uani 1 1 d . . . . .
C6D C 0.5243(5) 0.30417(8) -0.1000(3) 0.0346(6) Uani 1 1 d . . . . .
C5D C 0.3545(4) 0.33302(8) -0.1440(3) 0.0303(5) Uani 1 1 d . . . . .
C7C C 0.1930(4) 0.70642(8) 0.8999(3) 0.0322(5) Uani 1 1 d . . . . .
C6B C 0.9102(4) 0.67516(8) 0.3256(3) 0.0308(5) Uani 1 1 d . . . . .
C8B C 1.1048(5) 0.69333(10) 0.4161(3) 0.0414(6) Uani 1 1 d . . . . .
C7B C 0.7951(6) 0.71269(10) 0.2397(3) 0.0407(6) Uani 1 1 d . . . . .
C8A C 0.4960(6) 0.28164(10) 0.4006(4) 0.0443(7) Uani 1 1 d . . . . .
C7A C 0.7463(5) 0.34623(11) 0.4717(4) 0.0492(8) Uani 1 1 d . . . . .
H4A H 0.544(4) 0.4219(9) 0.339(3) 0.018(6) Uiso 1 1 d . . . . .
H1D H 0.514(4) 0.4610(8) -0.145(3) 0.014(5) Uiso 1 1 d . . . . .
H4B H 0.932(4) 0.6243(8) 0.586(3) 0.013(5) Uiso 1 1 d . . . . .
H10B H 0.674(4) 0.6738(9) 0.479(3) 0.023(6) Uiso 1 1 d . . . . .
H3B H 1.034(4) 0.5567(9) 0.495(3) 0.023(6) Uiso 1 1 d . . . . .
H3C H -0.266(4) 0.6201(9) 0.900(3) 0.023(6) Uiso 1 1 d . . . . .
H3D H 0.274(5) 0.3986(9) -0.188(3) 0.024(6) Uiso 1 1 d . . . . .
H2C H 0.371(6) 0.5740(11) 1.115(3) 0.038(8) Uiso 1 1 d . . . . .
H7D H 0.926(5) 0.3775(11) -0.061(3) 0.039(8) Uiso 1 1 d . . . . .
H6C H 0.315(5) 0.7299(11) 0.902(3) 0.037(8) Uiso 1 1 d . . . . .
H2B H 1.076(4) 0.5911(9) 0.369(3) 0.024(6) Uiso 1 1 d . . . . .
H6D H 0.857(6) 0.3003(12) -0.039(4) 0.046(9) Uiso 1 1 d . . . . .
H11B H 0.616(5) 0.6397(10) 0.346(3) 0.034(7) Uiso 1 1 d . . . . .
H5B H 0.514(4) 0.5799(9) 0.509(3) 0.021(6) Uiso 1 1 d . . . . .
H9B H 0.695(5) 0.5252(11) 0.624(3) 0.028(7) Uiso 1 1 d . . . . .
H15B H 1.059(5) 0.7160(12) 0.489(4) 0.043(8) Uiso 1 1 d . . . . .
H14B H 1.195(5) 0.6700(11) 0.472(3) 0.038(8) Uiso 1 1 d . . . . .
H8A H 0.293(4) 0.4949(10) 0.241(3) 0.026(7) Uiso 1 1 d . . . . .
H13A H 0.756(6) 0.3785(13) 0.506(4) 0.049(9) Uiso 1 1 d . . . . .
H8B H 0.852(6) 0.5563(12) 0.714(4) 0.044(8) Uiso 1 1 d . . . . .
H12A H 0.420(6) 0.3345(12) 0.524(4) 0.044(8) Uiso 1 1 d . . . . .
H6A H 0.300(5) 0.4117(11) 0.123(4) 0.036(8) Uiso 1 1 d . . . . .
H2D H 0.882(5) 0.4574(10) -0.275(3) 0.027(7) Uiso 1 1 d . . . . .
H14A H 0.826(5) 0.3418(11) 0.381(4) 0.041(8) Uiso 1 1 d . . . . .
H4D H 0.199(5) 0.3207(11) -0.162(3) 0.038(8) Uiso 1 1 d . . . . .
H7B H 0.606(5) 0.5480(11) 0.750(3) 0.040(8) Uiso 1 1 d . . . . .
H6B H 0.564(4) 0.6128(9) 0.643(3) 0.016(6) Uiso 1 1 d . . . . .
H4C H -0.345(5) 0.6949(10) 0.809(3) 0.031(7) Uiso 1 1 d . . . . .
H7A H 0.451(5) 0.4774(10) 0.141(3) 0.037(8) Uiso 1 1 d . . . . .
H7C H 0.377(6) 0.6545(11) 0.986(4) 0.044(8) Uiso 1 1 d . . . . .
H13B H 1.213(7) 0.7098(13) 0.355(4) 0.060(10) Uiso 1 1 d . . . . .
H5A H 0.102(5) 0.4262(10) 0.219(3) 0.031(7) Uiso 1 1 d . . . . .
H5C H -0.042(5) 0.7469(10) 0.809(3) 0.026(6) Uiso 1 1 d . . . . .
H1C H -0.026(4) 0.5687(8) 1.000(3) 0.016(6) Uiso 1 1 d . . . . .
H9A H 0.208(5) 0.4860(10) 0.097(3) 0.028(7) Uiso 1 1 d . . . . .
H15A H 0.820(7) 0.3263(14) 0.539(5) 0.064(11) Uiso 1 1 d . . . . .
H2A H 0.131(5) 0.4130(10) 0.477(3) 0.031(7) Uiso 1 1 d . . . . .
H17B H 0.740(6) 0.7384(12) 0.307(4) 0.049(9) Uiso 1 1 d . . . . .
H1A H 0.205(5) 0.5062(13) 0.674(4) 0.045(9) Uiso 1 1 d . . . . .
H17A H 0.576(7) 0.2628(14) 0.471(4) 0.062(11) Uiso 1 1 d . . . . .
H12B H 0.963(5) 0.6530(10) 0.261(3) 0.033(7) Uiso 1 1 d . . . . .
H5D H 0.498(5) 0.2734(11) -0.090(3) 0.039(8) Uiso 1 1 d . . . . .
H16B H 0.901(6) 0.7285(12) 0.178(4) 0.050(9) Uiso 1 1 d . . . . .
H18A H 0.597(7) 0.2767(16) 0.319(5) 0.075(12) Uiso 1 1 d . . . . .
H1B H 0.842(6) 0.4932(14) 0.231(5) 0.059(10) Uiso 1 1 d . . . . .
H3A H 0.369(5) 0.4055(11) 0.564(4) 0.040(8) Uiso 1 1 d . . . . .
H16A H 0.331(7) 0.2705(16) 0.382(5) 0.074(12) Uiso 1 1 d . . . . .
H18B H 0.652(6) 0.7000(13) 0.181(4) 0.055(10) Uiso 1 1 d . . . . .
H11A H 0.237(5) 0.3476(10) 0.306(3) 0.028(7) Uiso 1 1 d . . . . .
H10A H 0.474(5) 0.3508(10) 0.231(3) 0.036(7) 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
O1C C1C 1.266(3) . ?
O1A C1A 1.325(2) . ?
O1A H1A 0.92(4) . ?
O1D C1D 1.276(3) . ?
O2D C1D 1.242(3) . ?
O1B C1B 1.332(3) . ?
O1B H1B 0.92(4) . ?
O2C C1C 1.252(3) . ?
O2A C1A 1.220(3) . ?
O3D C2D 1.430(2) . ?
O3D H2D 0.86(3) . ?
O3C C2C 1.420(3) . ?
O3C H2C 0.86(4) . ?
O2B C1B 1.212(3) . ?
N1B C4B 1.499(3) . ?
N1B H9B 0.92(3) . ?
N1B H8B 0.99(4) . ?
N1B H7B 0.96(3) . ?
N1A C4A 1.490(3) . ?
N1A H8A 0.87(3) . ?
N1A H7A 0.93(3) . ?
N1A H9A 0.94(3) . ?
C1D C2D 1.528(3) . ?
C1C C2C 1.542(3) . ?
C3D C4D 1.391(3) . ?
C3D C2D 1.518(3) . ?
C3D C8D 1.391(3) . ?
C1B C2B 1.506(3) . ?
C1A C2A 1.505(3) . ?
C3C C4C 1.395(3) . ?
C3C C2C 1.517(3) . ?
C3C C8C 1.390(3) . ?
C3A C2A 1.529(3) . ?
C3A C4A 1.529(3) . ?
C3A C5A 1.540(3) . ?
C3A H4A 0.99(3) . ?
C4D C5D 1.389(3) . ?
C4D H3D 0.99(3) . ?
C3B C2B 1.540(3) . ?
C3B C4B 1.532(3) . ?
C3B C5B 1.535(3) . ?
C3B H4B 1.03(2) . ?
C2D H1D 0.97(2) . ?
C4C C5C 1.388(3) . ?
C4C H3C 1.02(3) . ?
C2C H1C 0.99(3) . ?
C8C C7C 1.388(4) . ?
C8C H7C 0.95(4) . ?
C2A H2A 0.98(3) . ?
C2A H3A 1.05(3) . ?
C2B H3B 0.98(3) . ?
C2B H2B 0.97(3) . ?
C5C C6C 1.386(4) . ?
C5C H4C 1.04(3) . ?
C6A C5A 1.531(3) . ?
C6A C8A 1.528(4) . ?
C6A C7A 1.515(4) . ?
C6A H12A 0.99(4) . ?
C4B H5B 0.99(3) . ?
C4B H6B 0.99(3) . ?
C8D C7D 1.387(4) . ?
C8D H7D 0.98(3) . ?
C5B C6B 1.528(3) . ?
C5B H10B 0.99(3) . ?
C5B H11B 1.02(3) . ?
C4A H6A 0.96(3) . ?
C4A H5A 0.97(3) . ?
C5A H11A 1.02(3) . ?
C5A H10A 0.98(3) . ?
C7D C6D 1.384(4) . ?
C7D H6D 0.99(4) . ?
C6C C7C 1.390(4) . ?
C6C H5C 0.94(3) . ?
C6D C5D 1.388(4) . ?
C6D H5D 0.94(3) . ?
C5D H4D 1.01(3) . ?
C7C H6C 1.02(3) . ?
C6B C8B 1.516(4) . ?
C6B C7B 1.527(4) . ?
C6B H12B 0.96(3) . ?
C8B H15B 1.01(4) . ?
C8B H14B 1.01(3) . ?
C8B H13B 1.01(4) . ?
C7B H17B 1.05(4) . ?
C7B H16B 1.00(4) . ?
C7B H18B 1.07(4) . ?
C8A H17A 0.98(4) . ?
C8A H18A 1.01(5) . ?
C8A H16A 1.06(5) . ?
C7A H13A 1.02(4) . ?
C7A H14A 1.00(4) . ?
C7A H15A 0.96(4) . ?

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
C1A O1A H1A 112(2) . . ?
C1B O1B H1B 109(2) . . ?
C2D O3D H2D 108.9(19) . . ?
C2C O3C H2C 107(2) . . ?
C4B N1B H9B 112.6(18) . . ?
C4B N1B H8B 111(2) . . ?
C4B N1B H7B 111.5(19) . . ?
H9B N1B H8B 109(3) . . ?
H9B N1B H7B 105(3) . . ?
H8B N1B H7B 107(3) . . ?
C4A N1A H8A 115.2(19) . . ?
C4A N1A H7A 107.2(19) . . ?
C4A N1A H9A 109.5(17) . . ?
H8A N1A H7A 109(3) . . ?
H8A N1A H9A 105(3) . . ?
H7A N1A H9A 110(3) . . ?
O1D C1D C2D 115.66(17) . . ?
O2D C1D O1D 125.91(19) . . ?
O2D C1D C2D 118.41(18) . . ?
O1C C1C C2C 117.30(17) . . ?
O2C C1C O1C 125.34(18) . . ?
O2C C1C C2C 117.35(17) . . ?
C4D C3D C2D 120.1(2) . . ?
C4D C3D C8D 118.9(2) . . ?
C8D C3D C2D 120.9(2) . . ?
O1B C1B C2B 112.17(18) . . ?
O2B C1B O1B 123.1(2) . . ?
O2B C1B C2B 124.7(2) . . ?
O1A C1A C2A 111.36(17) . . ?
O2A C1A O1A 123.39(19) . . ?
O2A C1A C2A 125.22(18) . . ?
C4C C3C C2C 120.71(19) . . ?
C8C C3C C4C 118.8(2) . . ?
C8C C3C C2C 120.5(2) . . ?
C2A C3A C4A 112.78(18) . . ?
C2A C3A C5A 110.36(18) . . ?
C2A C3A H4A 108.4(14) . . ?
C4A C3A C5A 106.40(17) . . ?
C4A C3A H4A 109.6(14) . . ?
C5A C3A H4A 109.3(15) . . ?
C3D C4D H3D 120.4(16) . . ?
C5D C4D C3D 120.7(2) . . ?
C5D C4D H3D 118.9(16) . . ?
C2B C3B H4B 106.2(13) . . ?
C4B C3B C2B 112.21(18) . . ?
C4B C3B C5B 107.99(18) . . ?
C4B C3B H4B 107.3(13) . . ?
C5B C3B C2B 114.61(18) . . ?
C5B C3B H4B 108.2(13) . . ?
O3D C2D C1D 110.94(17) . . ?
O3D C2D C3D 110.59(17) . . ?
O3D C2D H1D 108.2(14) . . ?
C1D C2D H1D 107.9(14) . . ?
C3D C2D C1D 110.93(17) . . ?
C3D C2D H1D 108.2(14) . . ?
C3C C4C H3C 118.2(15) . . ?
C5C C4C C3C 120.5(2) . . ?
C5C C4C H3C 121.3(15) . . ?
O3C C2C C1C 110.96(17) . . ?
O3C C2C C3C 112.12(17) . . ?
O3C C2C H1C 111.3(14) . . ?
C1C C2C H1C 108.0(14) . . ?
C3C C2C C1C 108.36(16) . . ?
C3C C2C H1C 105.8(14) . . ?
C3C C8C H7C 117(2) . . ?
C7C C8C C3C 120.8(2) . . ?
C7C C8C H7C 122(2) . . ?
C1A C2A C3A 117.05(18) . . ?
C1A C2A H2A 109.0(18) . . ?
C1A C2A H3A 101.6(18) . . ?
C3A C2A H2A 110.5(17) . . ?
C3A C2A H3A 110.4(18) . . ?
H2A C2A H3A 108(2) . . ?
C1B C2B C3B 116.59(18) . . ?
C1B C2B H3B 108.0(16) . . ?
C1B C2B H2B 103.0(15) . . ?
C3B C2B H3B 108.8(15) . . ?
C3B C2B H2B 112.1(16) . . ?
H3B C2B H2B 108(2) . . ?
C4C C5C H4C 119.5(17) . . ?
C6C C5C C4C 120.3(2) . . ?
C6C C5C H4C 120.1(17) . . ?
C5A C6A H12A 107(2) . . ?
C8A C6A C5A 109.6(2) . . ?
C8A C6A H12A 105(2) . . ?
C7A C6A C5A 112.4(2) . . ?
C7A C6A C8A 112.1(2) . . ?
C7A C6A H12A 111(2) . . ?
N1B C4B C3B 111.61(17) . . ?
N1B C4B H5B 107.7(15) . . ?
N1B C4B H6B 106.4(14) . . ?
C3B C4B H5B 112.8(15) . . ?
C3B C4B H6B 109.6(14) . . ?
H5B C4B H6B 108(2) . . ?
C3D C8D H7D 120.4(18) . . ?
C7D C8D C3D 120.5(2) . . ?
C7D C8D H7D 119.1(19) . . ?
C3B C5B H10B 108.7(15) . . ?
C3B C5B H11B 108.1(17) . . ?
C6B C5B C3B 115.85(19) . . ?
C6B C5B H10B 107.9(16) . . ?
C6B C5B H11B 108.7(17) . . ?
H10B C5B H11B 107(2) . . ?
N1A C4A C3A 114.96(18) . . ?
N1A C4A H6A 105.9(19) . . ?
N1A C4A H5A 107.4(17) . . ?
C3A C4A H6A 107.7(19) . . ?
C3A C4A H5A 110.3(17) . . ?
H6A C4A H5A 111(2) . . ?
C3A C5A H11A 108.2(16) . . ?
C3A C5A H10A 110.7(18) . . ?
C6A C5A C3A 117.45(18) . . ?
C6A C5A H11A 107.0(16) . . ?
C6A C5A H10A 104.8(18) . . ?
H11A C5A H10A 108(2) . . ?
C8D C7D H6D 120(2) . . ?
C6D C7D C8D 120.2(2) . . ?
C6D C7D H6D 120(2) . . ?
C5C C6C C7C 119.5(2) . . ?
C5C C6C H5C 121.6(17) . . ?
C7C C6C H5C 118.8(17) . . ?
C7D C6D C5D 119.8(2) . . ?
C7D C6D H5D 119.3(19) . . ?
C5D C6D H5D 120.9(19) . . ?
C4D C5D H4D 120.7(18) . . ?
C6D C5D C4D 119.9(2) . . ?
C6D C5D H4D 119.4(18) . . ?
C8C C7C C6C 120.1(2) . . ?
C8C C7C H6C 120.7(18) . . ?
C6C C7C H6C 119.2(17) . . ?
C5B C6B H12B 105.4(18) . . ?
C8B C6B C5B 113.2(2) . . ?
C8B C6B C7B 110.6(2) . . ?
C8B C6B H12B 108.9(18) . . ?
C7B C6B C5B 108.9(2) . . ?
C7B C6B H12B 109.8(18) . . ?
C6B C8B H15B 112.5(19) . . ?
C6B C8B H14B 114.9(18) . . ?
C6B C8B H13B 112(2) . . ?
H15B C8B H14B 106(3) . . ?
H15B C8B H13B 105(3) . . ?
H14B C8B H13B 106(3) . . ?
C6B C7B H17B 111.9(19) . . ?
C6B C7B H16B 111(2) . . ?
C6B C7B H18B 110(2) . . ?
H17B C7B H16B 103(3) . . ?
H17B C7B H18B 107(3) . . ?
H16B C7B H18B 113(3) . . ?
C6A C8A H17A 113(2) . . ?
C6A C8A H18A 107(3) . . ?
C6A C8A H16A 113(3) . . ?
H17A C8A H18A 97(3) . . ?
H17A C8A H16A 111(4) . . ?
H18A C8A H16A 116(4) . . ?
C6A C7A H13A 112(2) . . ?
C6A C7A H14A 105.8(19) . . ?
C6A C7A H15A 111(2) . . ?
H13A C7A H14A 112(3) . . ?
H13A C7A H15A 112(3) . . ?
H14A C7A H15A 104(3) . . ?

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
O1C C1C C2C O3C 171.73(17) . . . . ?
O1C C1C C2C C3C -64.8(2) . . . . ?
O1A C1A C2A C3A 176.23(19) . . . . ?
O1D C1D C2D O3D 172.24(18) . . . . ?
O1D C1D C2D C3D -64.4(2) . . . . ?
O2D C1D C2D O3D -9.2(3) . . . . ?
O2D C1D C2D C3D 114.2(2) . . . . ?
O1B C1B C2B C3B -145.35(18) . . . . ?
O2C C1C C2C O3C -9.7(3) . . . . ?
O2C C1C C2C C3C 113.8(2) . . . . ?
O2A C1A C2A C3A -5.6(3) . . . . ?
O2B C1B C2B C3B 36.4(3) . . . . ?
C3D C4D C5D C6D 0.9(4) . . . . ?
C3D C8D C7D C6D 0.2(4) . . . . ?
C3C C4C C5C C6C -0.9(3) . . . . ?
C3C C8C C7C C6C -0.1(4) . . . . ?
C4D C3D C2D O3D -95.9(2) . . . . ?
C4D C3D C2D C1D 140.57(19) . . . . ?
C4D C3D C8D C7D 1.0(4) . . . . ?
C3B C5B C6B C8B -57.4(3) . . . . ?
C3B C5B C6B C7B 179.2(2) . . . . ?
C2D C3D C4D C5D 176.8(2) . . . . ?
C2D C3D C8D C7D -177.3(2) . . . . ?
C4C C3C C2C O3C -133.0(2) . . . . ?
C4C C3C C2C C1C 104.2(2) . . . . ?
C4C C3C C8C C7C -1.6(3) . . . . ?
C4C C5C C6C C7C -0.8(4) . . . . ?
C2C C3C C4C C5C -175.12(19) . . . . ?
C2C C3C C8C C7C 175.6(2) . . . . ?
C8C C3C C4C C5C 2.1(3) . . . . ?
C8C C3C C2C O3C 49.9(3) . . . . ?
C8C C3C C2C C1C -72.9(2) . . . . ?
C2A C3A C4A N1A 82.3(2) . . . . ?
C2A C3A C5A C6A -54.8(3) . . . . ?
C2B C3B C4B N1B 53.0(2) . . . . ?
C2B C3B C5B C6B -50.7(3) . . . . ?
C5C C6C C7C C8C 1.3(4) . . . . ?
C4B C3B C2B C1B 55.1(2) . . . . ?
C4B C3B C5B C6B -176.56(19) . . . . ?
C8D C3D C4D C5D -1.5(3) . . . . ?
C8D C3D C2D O3D 82.4(3) . . . . ?
C8D C3D C2D C1D -41.2(3) . . . . ?
C8D C7D C6D C5D -0.8(4) . . . . ?
C5B C3B C2B C1B -68.5(3) . . . . ?
C5B C3B C4B N1B -179.71(17) . . . . ?
C4A C3A C2A C1A -71.8(3) . . . . ?
C4A C3A C5A C6A -177.5(2) . . . . ?
C5A C3A C2A C1A 169.40(19) . . . . ?
C5A C3A C4A N1A -156.58(18) . . . . ?
C7D C6D C5D C4D 0.3(4) . . . . ?
C8A C6A C5A C3A 179.1(2) . . . . ?
C7A C6A C5A C3A -55.5(3) . . . . ?

_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 1.487
_oxdiff_exptl_absorpt_empirical_full_min 0.786
####################################################################### 
# 
# 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_S-PGB_R-MAN
_database_code_depnum_ccdc_archive 'CCDC 2170103'
loop_
_audit_author_name
_audit_author_address
'Daniel Komisarek'
;Heinrich Heine University Duesseldorf
Germany
;
_audit_update_record             
;
2022-05-03 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_date             2021-09-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            '(S)-Pregabalin (R)-Mandelic Acid'
_chemical_name_systematic        
'(S)-3-isobutyl-Î³-aminobutyric acid (R)-2-Hydroxy-2-phenylacetic acid'
_chemical_formula_moiety         'C8 H18 N O2, C8 H7 O3'
_chemical_formula_sum            'C16 H25 N O5'
_chemical_formula_weight         311.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H18 N O2 C8 H7 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.07710(10)
_cell_length_b                   29.9265(5)
_cell_length_c                   9.30660(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.6620(10)
_cell_angle_gamma                90
_cell_volume                     1690.73(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14723
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      77.6270
_cell_measurement_theta_min      2.9660
_shelx_estimated_absorpt_T_max   0.896
_shelx_estimated_absorpt_T_min   0.689
_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_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -2 0.2533
1 1 0 0.1957
2 0 -5 0.3154
0 -19 -1 0.0560
2 16 -1 0.1427
0 19 1 0.0915
-1 17 2 0.1274
1 8 5 0.1527
-3 -8 -2 0.1526
3 8 1 0.1883
-3 13 -2 0.1314
1 11 -5 0.2217
0 -13 4 0.1759
-3 -1 3 0.2386
1 -14 3 0.1681
0 19 0 0.1028
1 18 -1 0.1350
-4 5 -2 0.1355
-2 17 -1 0.0960
1 15 -4 0.1827
0 -4 6 0.1701

_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.15
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 -0.9998 -1.9997 0.0643 0.2768 0.1783
1.0002 1.0103 -0.0029 -0.0351 -0.1495 0.2087
2.4601 0.0607 -4.8912 0.0697 0.3083 0.9487
-0.3232 -19.1114 -0.9429 0.9813 0.1836 -0.0574
2.2272 15.5178 -1.4061 -0.7499 -0.1427 0.6460
0.3054 19.1089 0.9624 -0.9816 -0.1836 0.0520
-1.0572 17.2407 2.3414 -0.9175 -0.1700 -0.3596
0.7245 7.5160 5.4002 -0.4086 -0.8570 -0.3139
-3.1718 -8.0959 -2.3309 0.3775 0.7989 -0.4682
3.4805 7.5035 1.3720 -0.3358 -0.7123 0.6163
-2.6042 12.9038 -1.9363 -0.6930 0.6540 -0.3032
0.9842 11.2726 -4.7466 -0.5311 0.5062 0.6794
-0.0208 -13.0887 4.4596 0.6423 -0.6102 -0.4638
-3.3154 -1.1165 3.4865 -0.0207 0.0142 -0.9997
1.4382 -14.0780 3.4276 0.7241 -0.6855 -0.0757
-0.0549 19.4203 -0.1568 -0.9963 0.0249 0.0817
1.1832 17.9727 -1.4856 -0.8928 0.0238 0.4499
-3.5312 5.3938 -1.8561 -0.3237 0.7836 -0.5303
-1.6413 17.0466 -1.3303 -0.8934 0.4251 -0.1450
0.9660 15.0704 -3.5765 -0.7339 0.3462 0.5844
0.4927 -3.7474 5.8366 0.1626 -0.8798 -0.4466

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    100.00 167.00   0.50    0.08    --  109.41  19.00 150.00  134
  2  ω    144.00 178.00   0.50    0.08    --  109.41  38.00   0.00   68
  3  ω    100.00 126.00   0.50    0.08    --  109.41  38.00   0.00   52
  4  ω    -48.00 -20.00   0.50    0.08    --  -90.00  38.00-150.00   56
  5  ω    -67.00 -32.00   0.50    0.08    --  -90.00  57.00-180.00   70
  6  ω    -47.00 -19.00   0.50    0.08    --  -90.00  38.00-120.00   56
  7  ω    -47.00 -18.00   0.50    0.08    --  -90.00  38.00 -90.00   58
  8  ω    -65.00 -40.00   0.50    0.08    --  -90.00  57.00 -30.00   50
  9  ω    -45.00 -20.00   0.50    0.08    --  -90.00  38.00 -30.00   50
 10  ω    -47.00 -20.00   0.50    0.08    --  -90.00  38.00  30.00   54
 11  ω    -46.00 -19.00   0.50    0.08    --  -90.00  38.00  90.00   54
 12  ω    -47.00 -22.00   0.50    0.08    --  -90.00  38.00 150.00   50
 13  ω    -31.00  24.00   0.50    0.05    --  -49.27  19.00 150.00  110
 14  ω    -26.00  19.00   0.50    0.05    --  -49.27  19.00-120.00   90
 15  ω    106.00 131.00   0.50    0.08    --  109.41 147.00-155.00   50
 16  ω    107.00 162.00   0.50    0.08    --  109.41 125.00 -30.00  110
 17  ω    112.00 137.00   0.50    0.08    --  109.41 125.00  39.00   50
 18  ω    -23.00  20.00   0.50    0.05    --   49.27 -19.00 -60.00   86
 19  ω     38.00  87.00   0.50    0.08    --  109.41 -77.00 -30.00   98
 20  ω     38.00  99.00   0.50    0.08    --  109.41 -77.00  30.00  122
 21  ω     51.00  91.00   0.50    0.08    --  109.41 -77.00  90.00   80
 22  ω     37.00  87.00   0.50    0.08    --  109.41 -99.00 150.00  100
 23  ω     96.00 124.00   0.50    0.08    --  109.41-147.00 155.00   56
 24  ω     75.00 104.00   0.50    0.05    --   49.27-147.00 155.00   58
 25  ω     81.00 109.00   0.50    0.08    --  109.41-125.00  60.00   56
 26  ω     50.00  76.00   0.50    0.08    --  109.41-125.00  60.00   52
 27  ω     43.00 101.00   0.50    0.08    --  109.41-125.00   0.00  116
 28  ω     72.00 110.00   0.50    0.08    --  109.41-125.00 -38.00   76
 29  ω     63.00 107.00   0.50    0.08    --  109.41-107.00 -65.01   88
 30  ω     49.00 109.00   0.50    0.08    --  109.41-125.00 -90.00  120
 31  ω     63.00 107.00   0.50    0.08    --  109.41-107.00-161.82   88
 32  ω     36.00  69.00   0.50    0.05    --   49.27-125.00 -38.00   66
 33  ω    -68.00 -40.00   0.50    0.05    --  -49.27 125.00  39.00   56
 34  ω    -87.00 -62.00   0.50    0.05    --  -49.27 147.00-155.00   50
 35  ω    -94.00 -62.00   0.50    0.08    --  -90.00 147.00-155.00   64
 36  ω    -85.00 -19.00   0.50    0.08    --  -90.00 125.00  39.00  132
 37  ω   -161.00 -82.00   0.50    0.08    --  -90.00 -38.00 150.00  158
 38  ω   -120.00 -32.00   0.50    0.05    --  -49.27 -77.00 -90.00  176
 39  ω   -120.00 -74.00   0.50    0.05    --  -49.27-125.00 -38.00   92
 40  ω   -118.00 -74.00   0.50    0.05    --  -49.27-125.00  60.00   88
 41  ω   -120.00 -73.00   0.50    0.05    --  -49.27-125.00 120.00   94
 42  ω    -95.00 -69.00   0.50    0.05    --  -49.27-147.00 155.00   52
 43  ω   -114.00 -68.00   0.50    0.08    --  -90.00-147.00 155.00   92
 44  ω   -124.00 -86.00   0.50    0.08    --  -90.00 -99.00  90.00   76
 45  ω   -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       'ω 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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_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_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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_coef       .
_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_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.050
_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/[σ²(Fo²)+(0.0808P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1205
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1C O 0.1545(3) 0.44442(7) 0.75425(19) 0.0248(4) Uani 1 1 d . . . . .
O1D O 0.7342(3) 0.53713(7) 0.09496(19) 0.0284(4) Uani 1 1 d . . . . .
O1A O 0.2020(3) 0.52261(7) 0.6437(2) 0.0280(4) Uani 1 1 d . . . . .
O2C O 0.4479(3) 0.44925(7) 0.90642(19) 0.0280(4) Uani 1 1 d . . . . .
O1B O 0.9142(3) 0.49148(7) 0.3027(2) 0.0301(4) Uani 1 1 d . . . . .
O2D O 0.9976(3) 0.52421(7) -0.0604(2) 0.0295(4) Uani 1 1 d . . . . .
O2A O 0.4100(3) 0.50057(7) 0.4647(2) 0.0282(4) Uani 1 1 d . . . . .
O008 O 0.7464(4) 0.54730(7) -0.2880(2) 0.0297(4) Uani 1 1 d . . . . .
O3C O 0.2415(4) 0.41739(8) 1.1285(2) 0.0329(5) Uani 1 1 d . . . . .
O2B O 0.6844(4) 0.43661(9) 0.2340(3) 0.0433(6) Uani 1 1 d . . . . .
N1A N 0.3088(4) 0.52365(9) 0.1690(2) 0.0266(5) Uani 1 1 d . . . . .
N1B N 0.7045(4) 0.44781(8) 0.6698(2) 0.0241(4) Uani 1 1 d . . . . .
C1C C 0.2528(4) 0.43863(9) 0.8754(3) 0.0216(5) Uani 1 1 d . . . . .
C1D C 0.8098(4) 0.53672(9) -0.0295(3) 0.0232(5) Uani 1 1 d . . . . .
C1B C 0.8370(4) 0.45012(10) 0.3098(3) 0.0273(5) Uani 1 1 d . . . . .
C3C C 0.0725(4) 0.36815(10) 0.9466(3) 0.0251(5) Uani 1 1 d . . . . .
C3A C 0.3915(4) 0.58962(9) 0.3348(3) 0.0256(5) Uani 1 1 d . . . . .
C3D C 0.6106(4) 0.60428(10) -0.1296(3) 0.0273(5) Uani 1 1 d . . . . .
C1A C 0.3079(4) 0.52959(9) 0.5250(3) 0.0237(5) Uani 1 1 d . . . . .
C3B C 0.8310(4) 0.38801(9) 0.5036(3) 0.0245(5) Uani 1 1 d . . . . .
C2D C 0.6570(4) 0.55491(9) -0.1509(3) 0.0245(5) Uani 1 1 d . . . . .
C2B C 0.9640(4) 0.42264(9) 0.4215(3) 0.0249(5) Uani 1 1 d . . . . .
C2C C 0.1236(4) 0.41579(10) 0.9936(3) 0.0253(5) Uani 1 1 d . . . . .
C4D C 0.4005(5) 0.62114(11) -0.1569(3) 0.0315(6) Uani 1 1 d . . . . .
C2A C 0.2904(5) 0.57719(10) 0.4767(3) 0.0306(6) Uani 1 1 d . . . . .
C4A C 0.2611(5) 0.57090(11) 0.2039(3) 0.0301(6) Uani 1 1 d . . . . .
C4C C -0.1383(5) 0.35630(10) 0.8962(3) 0.0308(6) Uani 1 1 d . . . . .
C5A C 0.3967(5) 0.64056(11) 0.3164(3) 0.0320(6) Uani 1 1 d . . . . .
C5B C 0.7434(5) 0.34855(10) 0.4127(3) 0.0310(6) Uani 1 1 d . . . . .
C4B C 0.6352(4) 0.40897(10) 0.5765(3) 0.0250(5) Uani 1 1 d . . . . .
C6A C 0.5149(6) 0.66793(12) 0.4348(4) 0.0396(7) Uani 1 1 d . . . . .
C5C C -0.1808(6) 0.31354(12) 0.8432(4) 0.0395(7) Uani 1 1 d . . . . .
C8D C 0.7790(5) 0.63320(12) -0.0844(4) 0.0400(7) Uani 1 1 d . . . . .
C8C C 0.2378(5) 0.33601(11) 0.9490(4) 0.0356(6) Uani 1 1 d . . . . .
C6C C -0.0133(6) 0.28215(12) 0.8431(4) 0.0437(8) Uani 1 1 d . . . . .
C7D C 0.7378(6) 0.67865(12) -0.0706(5) 0.0489(9) Uani 1 1 d . . . . .
C7C C 0.1950(6) 0.29342(13) 0.8969(5) 0.0454(8) Uani 1 1 d . . . . .
C5D C 0.3607(6) 0.66660(13) -0.1445(4) 0.0411(7) Uani 1 1 d . . . . .
C8B C 1.1073(7) 0.30689(16) 0.4153(5) 0.0544(10) Uani 1 1 d . . . . .
C6D C 0.5284(7) 0.69531(12) -0.1024(5) 0.0487(8) Uani 1 1 d . . . . .
C6B C 0.9139(6) 0.32441(11) 0.3243(4) 0.0398(7) Uani 1 1 d . . . . .
C7B C 0.7985(9) 0.28695(15) 0.2391(4) 0.0534(10) Uani 1 1 d . . . . .
C7A C 0.7514(8) 0.65336(19) 0.4656(8) 0.0687(14) Uani 1 1 d . . . . .
C8A C 0.4946(10) 0.71775(15) 0.4004(6) 0.0623(11) Uani 1 1 d . . . . .
H4A H 0.544(6) 0.5792(12) 0.339(4) 0.023(8) Uiso 1 1 d . . . . .
H1D H 0.514(5) 0.5389(12) -0.155(3) 0.020(7) Uiso 1 1 d . . . . .
H4B H 0.938(5) 0.3739(12) 0.583(4) 0.022(7) Uiso 1 1 d . . . . .
H11B H 0.688(7) 0.3240(17) 0.482(5) 0.045(11) Uiso 1 1 d . . . . .
H7D H 0.926(7) 0.6211(16) -0.054(5) 0.047(11) Uiso 1 1 d . . . . .
H6C H 0.302(7) 0.2738(15) 0.904(4) 0.035(9) Uiso 1 1 d . . . . .
H3D H 0.280(6) 0.6028(14) -0.193(4) 0.033(9) Uiso 1 1 d . . . . .
H6A H 0.115(7) 0.5726(15) 0.218(5) 0.038(10) Uiso 1 1 d . . . . .
H2C H 0.363(7) 0.4232(14) 1.117(4) 0.032(10) Uiso 1 1 d . . . . .
H6D H 0.860(8) 0.6972(18) -0.041(6) 0.053(12) Uiso 1 1 d . . . . .
H5A H 0.298(9) 0.5862(19) 0.118(6) 0.060(13) Uiso 1 1 d . . . . .
H3C H -0.264(7) 0.3789(17) 0.899(5) 0.048(11) Uiso 1 1 d . . . . .
H10B H 0.629(7) 0.3586(15) 0.345(5) 0.039(10) Uiso 1 1 d . . . . .
H7C H 0.386(7) 0.3469(14) 0.983(4) 0.034(9) Uiso 1 1 d . . . . .
H6B H 0.524(6) 0.4212(13) 0.507(4) 0.030(8) Uiso 1 1 d . . . . .
H10A H 0.470(7) 0.6472(16) 0.232(5) 0.047(11) Uiso 1 1 d . . . . .
H8B H 0.702(6) 0.4724(15) 0.612(4) 0.032(9) Uiso 1 1 d . . . . .
H18B H 1.193(9) 0.334(2) 0.482(6) 0.065(14) Uiso 1 1 d . . . . .
H3B H 1.036(5) 0.4461(13) 0.496(4) 0.027(8) Uiso 1 1 d . . . . .
H12A H 0.449(9) 0.665(2) 0.524(7) 0.063(14) Uiso 1 1 d . . . . .
H2D H 0.884(7) 0.5440(14) -0.278(4) 0.031(9) Uiso 1 1 d . . . . .
H16B H 1.215(11) 0.290(2) 0.354(8) 0.084(18) Uiso 1 1 d . . . . .
H15B H 0.762(8) 0.261(2) 0.309(6) 0.063(14) Uiso 1 1 d . . . . .
H5B H 0.566(6) 0.3878(14) 0.643(4) 0.030(9) Uiso 1 1 d . . . . .
H7B H 0.608(6) 0.4498(14) 0.746(4) 0.032(9) Uiso 1 1 d . . . . .
H2B H 1.083(5) 0.4087(13) 0.363(4) 0.025(8) Uiso 1 1 d . . . . .
H1C H -0.018(5) 0.4308(11) 0.997(3) 0.019(7) Uiso 1 1 d . . . . .
H14B H 0.666(9) 0.298(2) 0.179(6) 0.065(15) Uiso 1 1 d . . . . .
H1B H 0.847(7) 0.5085(16) 0.223(5) 0.044(11) Uiso 1 1 d . . . . .
H11A H 0.227(7) 0.6516(16) 0.302(5) 0.043(11) Uiso 1 1 d . . . . .
H13B H 0.892(9) 0.273(2) 0.183(7) 0.068(15) Uiso 1 1 d . . . . .
H5C H -0.045(7) 0.2541(16) 0.805(5) 0.041(10) Uiso 1 1 d . . . . .
H8A H 0.294(5) 0.5066(13) 0.239(4) 0.021(8) Uiso 1 1 d . . . . .
H15A H 0.808(7) 0.6587(15) 0.379(5) 0.034(10) Uiso 1 1 d . . . . .
H4C H -0.347(8) 0.3050(18) 0.802(5) 0.054(12) Uiso 1 1 d . . . . .
H18A H 0.578(9) 0.737(2) 0.467(6) 0.063(14) Uiso 1 1 d . . . . .
H7A H 0.439(7) 0.5224(14) 0.139(4) 0.034(9) Uiso 1 1 d . . . . .
H2A H 0.360(8) 0.5921(17) 0.556(6) 0.052(12) Uiso 1 1 d . . . . .
H17B H 1.054(8) 0.2863(18) 0.487(6) 0.054(13) Uiso 1 1 d . . . . .
H3A H 0.139(8) 0.5893(17) 0.479(5) 0.047(11) Uiso 1 1 d . . . . .
H13A H 0.774(9) 0.621(2) 0.483(6) 0.065(14) Uiso 1 1 d . . . . .
H16A H 0.330(13) 0.728(3) 0.390(8) 0.09(2) Uiso 1 1 d . . . . .
H9B H 0.851(9) 0.444(2) 0.710(6) 0.059(13) Uiso 1 1 d . . . . .
H4D H 0.215(9) 0.6791(19) -0.163(6) 0.064(14) Uiso 1 1 d . . . . .
H9A H 0.208(7) 0.5159(15) 0.097(5) 0.038(10) Uiso 1 1 d . . . . .
H5D H 0.511(8) 0.7290(18) -0.096(5) 0.054(12) Uiso 1 1 d . . . . .
H17A H 0.579(9) 0.722(2) 0.312(7) 0.070(16) Uiso 1 1 d . . . . .
H12B H 0.962(6) 0.3488(15) 0.257(4) 0.036(10) Uiso 1 1 d . . . . .
H1A H 0.217(8) 0.495(2) 0.678(5) 0.053(12) Uiso 1 1 d . . . . .
H14A H 0.832(15) 0.677(3) 0.547(10) 0.12(3) 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
O1C C1C 1.264(3) . ?
O1D C1D 1.266(3) . ?
O1A C1A 1.320(3) . ?
O1A H1A 0.90(6) . ?
O2C C1C 1.248(3) . ?
O1B C1B 1.326(4) . ?
O1B H1B 0.97(5) . ?
O2D C1D 1.247(3) . ?
O2A C1A 1.219(3) . ?
O008 C2D 1.428(3) . ?
O008 H2D 0.84(4) . ?
O3C C2C 1.417(3) . ?
O3C H2C 0.77(5) . ?
O2B C1B 1.209(4) . ?
N1A C4A 1.482(4) . ?
N1A H8A 0.84(4) . ?
N1A H7A 0.85(4) . ?
N1A H9A 0.91(4) . ?
N1B C4B 1.499(4) . ?
N1B H8B 0.91(5) . ?
N1B H7B 0.94(4) . ?
N1B H9B 0.96(5) . ?
C1C C2C 1.541(3) . ?
C1D C2D 1.529(4) . ?
C1B C2B 1.509(4) . ?
C3C C2C 1.519(4) . ?
C3C C4C 1.389(4) . ?
C3C C8C 1.390(4) . ?
C3A C2A 1.529(4) . ?
C3A C4A 1.528(4) . ?
C3A C5A 1.535(4) . ?
C3A H4A 0.98(4) . ?
C3D C2D 1.519(4) . ?
C3D C4D 1.385(4) . ?
C3D C8D 1.390(4) . ?
C1A C2A 1.496(4) . ?
C3B C2B 1.539(4) . ?
C3B C5B 1.534(4) . ?
C3B C4B 1.531(4) . ?
C3B H4B 1.05(3) . ?
C2D H1D 0.99(3) . ?
C2B H3B 1.06(4) . ?
C2B H2B 1.02(4) . ?
C2C H1C 0.97(3) . ?
C4D C5D 1.387(5) . ?
C4D H3D 0.96(4) . ?
C2A H2A 0.94(5) . ?
C2A H3A 0.99(5) . ?
C4A H6A 0.90(4) . ?
C4A H5A 0.96(6) . ?
C4C C5C 1.391(5) . ?
C4C H3C 1.02(5) . ?
C5A C6A 1.526(4) . ?
C5A H10A 0.94(5) . ?
C5A H11A 1.08(4) . ?
C5B C6B 1.533(4) . ?
C5B H11B 1.05(5) . ?
C5B H10B 0.96(4) . ?
C4B H6B 0.98(4) . ?
C4B H5B 0.99(4) . ?
C6A C7A 1.517(6) . ?
C6A C8A 1.529(6) . ?
C6A H12A 0.94(6) . ?
C5C C6C 1.385(6) . ?
C5C H4C 1.09(5) . ?
C8D C7D 1.390(5) . ?
C8D H7D 0.99(5) . ?
C8C C7C 1.384(5) . ?
C8C H7C 1.00(4) . ?
C6C C7C 1.381(6) . ?
C6C H5C 0.93(5) . ?
C7D C6D 1.386(6) . ?
C7D H6D 0.96(5) . ?
C7C H6C 0.88(4) . ?
C5D C6D 1.376(6) . ?
C5D H4D 0.97(6) . ?
C8B C6B 1.510(6) . ?
C8B H18B 1.14(6) . ?
C8B H16B 1.02(7) . ?
C8B H17B 0.98(6) . ?
C6D H5D 1.02(5) . ?
C6B C7B 1.525(5) . ?
C6B H12B 1.02(4) . ?
C7B H15B 1.05(6) . ?
C7B H14B 1.01(6) . ?
C7B H13B 0.89(7) . ?
C7A H15A 0.90(5) . ?
C7A H13A 0.98(6) . ?
C7A H14A 1.13(10) . ?
C8A H18A 0.96(6) . ?
C8A H16A 1.05(8) . ?
C8A H17A 1.00(6) . ?

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
C1A O1A H1A 113(3) . . ?
C1B O1B H1B 113(3) . . ?
C2D O008 H2D 110(3) . . ?
C2C O3C H2C 109(3) . . ?
C4A N1A H8A 112(2) . . ?
C4A N1A H7A 108(3) . . ?
C4A N1A H9A 106(3) . . ?
H8A N1A H7A 111(4) . . ?
H8A N1A H9A 109(4) . . ?
H7A N1A H9A 110(4) . . ?
C4B N1B H8B 107(3) . . ?
C4B N1B H7B 108(2) . . ?
C4B N1B H9B 111(3) . . ?
H8B N1B H7B 114(4) . . ?
H8B N1B H9B 109(4) . . ?
H7B N1B H9B 108(4) . . ?
O1C C1C C2C 117.5(2) . . ?
O2C C1C O1C 125.2(2) . . ?
O2C C1C C2C 117.3(2) . . ?
O1D C1D C2D 116.0(2) . . ?
O2D C1D O1D 126.1(2) . . ?
O2D C1D C2D 117.9(2) . . ?
O1B C1B C2B 111.9(2) . . ?
O2B C1B O1B 123.1(3) . . ?
O2B C1B C2B 125.0(3) . . ?
C4C C3C C2C 120.6(3) . . ?
C4C C3C C8C 118.9(3) . . ?
C8C C3C C2C 120.5(3) . . ?
C2A C3A C5A 110.4(2) . . ?
C2A C3A H4A 108(2) . . ?
C4A C3A C2A 112.7(2) . . ?
C4A C3A C5A 106.7(2) . . ?
C4A C3A H4A 112(2) . . ?
C5A C3A H4A 107(2) . . ?
C4D C3D C2D 120.4(3) . . ?
C4D C3D C8D 119.2(3) . . ?
C8D C3D C2D 120.4(3) . . ?
O1A C1A C2A 111.8(2) . . ?
O2A C1A O1A 123.4(3) . . ?
O2A C1A C2A 124.8(2) . . ?
C2B C3B H4B 107.3(19) . . ?
C5B C3B C2B 114.9(2) . . ?
C5B C3B H4B 105.4(19) . . ?
C4B C3B C2B 112.4(2) . . ?
C4B C3B C5B 107.6(2) . . ?
C4B C3B H4B 108.8(19) . . ?
O008 C2D C1D 111.1(2) . . ?
O008 C2D C3D 110.6(2) . . ?
O008 C2D H1D 105.1(19) . . ?
C1D C2D H1D 110.8(19) . . ?
C3D C2D C1D 111.1(2) . . ?
C3D C2D H1D 108(2) . . ?
C1B C2B C3B 116.5(2) . . ?
C1B C2B H3B 106(2) . . ?
C1B C2B H2B 102(2) . . ?
C3B C2B H3B 109.2(19) . . ?
C3B C2B H2B 113(2) . . ?
H3B C2B H2B 110(3) . . ?
O3C C2C C1C 111.3(2) . . ?
O3C C2C C3C 112.0(2) . . ?
O3C C2C H1C 111.4(19) . . ?
C1C C2C H1C 107.5(19) . . ?
C3C C2C C1C 108.3(2) . . ?
C3C C2C H1C 106(2) . . ?
C3D C4D C5D 120.3(3) . . ?
C3D C4D H3D 122(2) . . ?
C5D C4D H3D 117(2) . . ?
C3A C2A H2A 112(3) . . ?
C3A C2A H3A 110(3) . . ?
C1A C2A C3A 117.7(2) . . ?
C1A C2A H2A 101(3) . . ?
C1A C2A H3A 113(3) . . ?
H2A C2A H3A 101(4) . . ?
N1A C4A C3A 115.2(2) . . ?
N1A C4A H6A 107(3) . . ?
N1A C4A H5A 103(3) . . ?
C3A C4A H6A 110(3) . . ?
C3A C4A H5A 111(3) . . ?
H6A C4A H5A 111(4) . . ?
C3C C4C C5C 120.5(3) . . ?
C3C C4C H3C 120(3) . . ?
C5C C4C H3C 119(3) . . ?
C3A C5A H10A 108(3) . . ?
C3A C5A H11A 107(2) . . ?
C6A C5A C3A 117.7(2) . . ?
C6A C5A H10A 105(3) . . ?
C6A C5A H11A 110(2) . . ?
H10A C5A H11A 108(4) . . ?
C3B C5B H11B 108(3) . . ?
C3B C5B H10B 110(3) . . ?
C6B C5B C3B 115.6(2) . . ?
C6B C5B H11B 104(3) . . ?
C6B C5B H10B 106(2) . . ?
H11B C5B H10B 112(3) . . ?
N1B C4B C3B 111.7(2) . . ?
N1B C4B H6B 105(2) . . ?
N1B C4B H5B 104(2) . . ?
C3B C4B H6B 112(2) . . ?
C3B C4B H5B 112(2) . . ?
H6B C4B H5B 111(3) . . ?
C5A C6A C8A 110.0(3) . . ?
C5A C6A H12A 113(3) . . ?
C7A C6A C5A 113.1(3) . . ?
C7A C6A C8A 112.8(4) . . ?
C7A C6A H12A 104(3) . . ?
C8A C6A H12A 104(4) . . ?
C4C C5C H4C 119(3) . . ?
C6C C5C C4C 120.0(3) . . ?
C6C C5C H4C 121(3) . . ?
C3D C8D H7D 120(3) . . ?
C7D C8D C3D 120.3(3) . . ?
C7D C8D H7D 120(3) . . ?
C3C C8C H7C 115(2) . . ?
C7C C8C C3C 120.5(3) . . ?
C7C C8C H7C 124(2) . . ?
C5C C6C H5C 118(3) . . ?
C7C C6C C5C 119.7(3) . . ?
C7C C6C H5C 122(3) . . ?
C8D C7D H6D 117(3) . . ?
C6D C7D C8D 120.0(3) . . ?
C6D C7D H6D 123(3) . . ?
C8C C7C H6C 118(3) . . ?
C6C C7C C8C 120.4(3) . . ?
C6C C7C H6C 122(3) . . ?
C4D C5D H4D 122(3) . . ?
C6D C5D C4D 120.4(3) . . ?
C6D C5D H4D 118(3) . . ?
C6B C8B H18B 112(3) . . ?
C6B C8B H16B 111(4) . . ?
C6B C8B H17B 109(3) . . ?
H18B C8B H16B 112(5) . . ?
H18B C8B H17B 104(4) . . ?
H16B C8B H17B 108(5) . . ?
C7D C6D H5D 116(3) . . ?
C5D C6D C7D 119.8(3) . . ?
C5D C6D H5D 124(3) . . ?
C5B C6B H12B 102(2) . . ?
C8B C6B C5B 113.0(3) . . ?
C8B C6B C7B 111.3(3) . . ?
C8B C6B H12B 111(2) . . ?
C7B C6B C5B 108.6(3) . . ?
C7B C6B H12B 110(2) . . ?
C6B C7B H15B 110(3) . . ?
C6B C7B H14B 113(3) . . ?
C6B C7B H13B 111(4) . . ?
H15B C7B H14B 113(4) . . ?
H15B C7B H13B 99(5) . . ?
H14B C7B H13B 110(5) . . ?
C6A C7A H15A 100(3) . . ?
C6A C7A H13A 116(3) . . ?
C6A C7A H14A 109(5) . . ?
H15A C7A H13A 105(5) . . ?
H15A C7A H14A 108(6) . . ?
H13A C7A H14A 117(6) . . ?
C6A C8A H18A 114(4) . . ?
C6A C8A H16A 113(5) . . ?
C6A C8A H17A 106(4) . . ?
H18A C8A H16A 110(6) . . ?
H18A C8A H17A 100(5) . . ?
H16A C8A H17A 114(6) . . ?

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
O1C C1C C2C O3C -171.4(2) . . . . ?
O1C C1C C2C C3C 65.0(3) . . . . ?
O1D C1D C2D O008 -172.1(2) . . . . ?
O1D C1D C2D C3D 64.2(3) . . . . ?
O1A C1A C2A C3A -175.8(2) . . . . ?
O2C C1C C2C O3C 9.8(3) . . . . ?
O2C C1C C2C C3C -113.8(3) . . . . ?
O1B C1B C2B C3B 145.2(2) . . . . ?
O2D C1D C2D O008 10.0(3) . . . . ?
O2D C1D C2D C3D -113.7(3) . . . . ?
O2A C1A C2A C3A 5.3(4) . . . . ?
O2B C1B C2B C3B -35.5(4) . . . . ?
C3C C4C C5C C6C 1.3(5) . . . . ?
C3C C8C C7C C6C -0.7(5) . . . . ?
C3A C5A C6A C7A 55.2(5) . . . . ?
C3A C5A C6A C8A -177.7(3) . . . . ?
C3D C4D C5D C6D -1.2(5) . . . . ?
C3D C8D C7D C6D -0.2(6) . . . . ?
C3B C5B C6B C8B 57.0(4) . . . . ?
C3B C5B C6B C7B -179.0(3) . . . . ?
C2D C3D C4D C5D -176.7(3) . . . . ?
C2D C3D C8D C7D 177.4(3) . . . . ?
C2B C3B C5B C6B 51.0(3) . . . . ?
C2B C3B C4B N1B -53.1(3) . . . . ?
C2C C3C C4C C5C 175.2(3) . . . . ?
C2C C3C C8C C7C -175.5(3) . . . . ?
C4D C3D C2D O008 97.2(3) . . . . ?
C4D C3D C2D C1D -138.8(3) . . . . ?
C4D C3D C8D C7D -1.7(5) . . . . ?
C4D C5D C6D C7D -0.7(6) . . . . ?
C2A C3A C4A N1A -82.0(3) . . . . ?
C2A C3A C5A C6A 56.2(3) . . . . ?
C4A C3A C2A C1A 71.3(3) . . . . ?
C4A C3A C5A C6A 179.0(3) . . . . ?
C4C C3C C2C O3C 132.3(3) . . . . ?
C4C C3C C2C C1C -104.5(3) . . . . ?
C4C C3C C8C C7C 2.5(5) . . . . ?
C4C C5C C6C C7C 0.6(5) . . . . ?
C5A C3A C2A C1A -169.4(2) . . . . ?
C5A C3A C4A N1A 156.6(2) . . . . ?
C5B C3B C2B C1B 68.2(3) . . . . ?
C5B C3B C4B N1B 179.4(2) . . . . ?
C4B C3B C2B C1B -55.3(3) . . . . ?
C4B C3B C5B C6B 177.0(2) . . . . ?
C5C C6C C7C C8C -0.9(6) . . . . ?
C8D C3D C2D O008 -81.9(3) . . . . ?
C8D C3D C2D C1D 42.1(3) . . . . ?
C8D C3D C4D C5D 2.4(4) . . . . ?
C8D C7D C6D C5D 1.4(7) . . . . ?
C8C C3C C2C O3C -49.7(3) . . . . ?
C8C C3C C2C C1C 73.4(3) . . . . ?
C8C C3C C4C C5C -2.8(4) . . . . ?

_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
####################################################################### 
# 
# 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_S-PGB_S-Mandelic_Acid
_database_code_depnum_ccdc_archive 'CCDC 2170108'
loop_
_audit_author_name
_audit_author_address
'Daniel Komisarek'
;Heinrich Heine University Duesseldorf
Germany
;
_audit_update_record             
;
2022-05-03 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_date             2021-09-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_name_common            '(S)-Pregabalin (S)-Mandelic Acid'
_chemical_name_systematic        
'(S)-3-isobutyl-Î³-aminobutyric acid (S)-2-Hydroxy-2-phenylacetic acid'
_chemical_formula_moiety         'C8 H17 N O2, C8 H8 O3'
_chemical_formula_sum            'C16 H25 N O5'
_chemical_formula_weight         311.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H17 N O2 C8 H8 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.24550(10)
_cell_length_b                   27.3880(5)
_cell_length_c                   9.9624(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.462(2)
_cell_angle_gamma                90
_cell_volume                     1704.03(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11933
_cell_measurement_temperature    99.98(13)
_cell_measurement_theta_max      76.8230
_cell_measurement_theta_min      3.1950
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.670
_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_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 0 0.2677
0 -1 6 0.0958
4 -7 1 0.2716
0 -18 0 0.0231
0 12 -5 0.1063
-3 0 -3 0.2773
0 -12 5 0.0746
3 11 -2 0.2251
0 -8 -6 0.0943
4 1 -1 0.2876
-3 -6 -3 0.2547
-2 5 5 0.2452
0 18 0 0.0389

_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0002 -1.0021 -0.0023 -0.0011 0.0595 0.2460
0.0812 -1.0817 6.4507 0.2260 0.9435 -0.2423
3.5819 -7.4394 1.3262 0.6335 -0.0794 -0.7697
0.0530 -17.7703 -0.1570 0.9597 -0.1259 0.2514
0.0003 11.7842 -4.8393 -0.7594 -0.6506 0.0084
-3.4635 0.4637 -3.3161 -0.3001 -0.2618 0.9173
-0.0667 -11.8654 4.8126 0.7594 0.6505 0.0091
2.9613 11.0484 -1.8648 -0.4810 -0.4080 -0.7760
0.0870 -7.6825 -5.8304 0.2728 -0.9116 0.3075
3.9930 1.3995 -1.0538 0.1181 -0.4092 -0.9047
-3.1822 -6.4817 -3.2007 0.0938 -0.3019 0.9487
-2.4630 4.7403 4.8692 -0.2692 0.9082 0.3204
0.0599 17.7674 0.1865 -0.9525 0.1229 -0.2785

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00   5.00   0.50    0.05    --   49.26 -19.00  30.00   58
  2  ω     10.00  60.00   0.50    0.05    --   49.26 -57.00-120.00  100
  3  ω    112.00 138.00   0.50    0.19    --  109.41 108.00 128.00   52
  4  ω     49.00  89.00   0.50    0.19    --  109.41 -77.00  90.00   80
  5  ω     81.00 106.00   0.50    0.19    --  109.41 -99.00 150.00   50
  6  ω     38.00  76.00   0.50    0.19    --  109.41-125.00  90.00   76
  7  ω     45.00 106.00   0.50    0.19    --  109.41-125.00 -30.00  122
  8  ω     78.00 109.00   0.50    0.19    --  109.41-125.00 -90.00   62
  9  ω     70.00 112.00   0.50    0.19    --  109.41-125.00-120.00   84
 10  ω     39.00  68.00   0.50    0.19    --  109.41-125.00-120.00   58
 11  ω     45.00  70.00   0.50    0.19    --  109.41-125.00 -90.00   50
 12  ω     45.00 109.00   0.50    0.19    --  109.41-125.00   0.00  128
 13  ω     82.00 112.00   0.50    0.19    --  109.41-125.00  90.00   60
 14  ω     30.00  55.00   0.50    0.05    --   49.26-108.00  31.00   50
 15  ω     57.00  83.00   0.50    0.19    --  109.41-108.00  31.00   52
 16  ω     41.00  95.00   0.50    0.19    --  109.41 -99.00  30.00  108
 17  ω     81.00 108.00   0.50    0.19    --  109.41-111.00 100.70   54
 18  ω     38.00  78.00   0.50    0.19    --  109.41-111.00 100.70   80
 19  ω    -59.00 -19.00   0.50    0.19    --  -90.00 125.00  60.00   80
 20  ω    -81.00 -36.00   0.50    0.19    --  -90.00 108.00 128.00   90
 21  ω    -82.00  -8.00   0.50    0.05    --  -49.26 108.00 128.00  148
 22  ω    -50.00 -23.00   0.50    0.19    --  -90.00 125.00 -30.00   54
 23  ω   -108.00 -76.00   0.50    0.19    --  -90.00  77.00 -30.00   64
 24  ω    -46.00 -19.00   0.50    0.19    --  -90.00  77.00 -30.00   54
 25  ω    -48.00 -22.00   0.50    0.19    --  -90.00  38.00 -90.00   52
 26  ω    -48.00 -18.00   0.50    0.19    --  -90.00  38.00-120.00   60
 27  ω    -47.00 -19.00   0.50    0.19    --  -90.00  38.00-180.00   56
 28  ω    -48.00 -19.00   0.50    0.19    --  -90.00  38.00-150.00   58
 29  ω    -48.00 -20.00   0.50    0.19    --  -90.00  38.00 -60.00   56
 30  ω    -48.00 -18.00   0.50    0.19    --  -90.00  38.00 -30.00   60
 31  ω    -47.00 -22.00   0.50    0.19    --  -90.00  38.00   0.00   50
 32  ω    -47.00 -19.00   0.50    0.19    --  -90.00  38.00 150.00   56
 33  ω    -31.00  24.00   0.50    0.05    --  -49.26  19.00  60.00  110
 34  ω   -116.00 -41.00   0.50    0.05    --  -49.26 -57.00 -30.00  150
 35  ω   -120.00 -81.00   0.50    0.05    --  -49.26-125.00  60.00   78
 36  ω   -159.00 -76.00   0.50    0.19    --  -90.00 -57.00 -60.00  166
 37  ω   -120.00 -95.00   0.50    0.05    --  -49.26-125.00-150.00   50
 38  ω   -120.00 -73.00   0.50    0.05    --  -49.26-125.00-180.00   94
 39  ω   -145.00-120.00   0.50    0.19    --  -90.00 -99.00 -60.00   50
 40  ω   -161.00-135.00   0.50    0.19    --  -90.00 -99.00-120.00   52
 41  ω   -128.00 -88.00   0.50    0.19    --  -90.00 -99.00-120.00   80
 42  ω   -111.00 -86.00   0.50    0.19    --  -90.00 -99.00 -60.00   50
 43  ω   -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       'ω 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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_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_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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_coef       .
_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_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.084
_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/[σ²(Fo²)+(0.0583P)²+0.4320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1186
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1D O 0.2862(4) 0.45090(9) 0.4676(2) 0.0272(5) Uani 1 1 d . . . . .
O2C O 0.7065(4) 0.50225(9) 0.6095(2) 0.0275(5) Uani 1 1 d . . . . .
O2B O 0.4248(3) 0.51093(9) 0.1830(2) 0.0266(5) Uani 1 1 d . . . . .
O2A O 0.9289(4) 0.48801(9) 1.0739(2) 0.0266(5) Uani 1 1 d . . . . .
O1A O 0.6809(4) 0.47429(9) 0.9171(2) 0.0278(5) Uani 1 1 d . . . . .
O1B O 0.1793(4) 0.52522(9) 0.3392(2) 0.0266(5) Uani 1 1 d . . . . .
O2D O 0.2068(4) 0.49616(9) 0.6470(2) 0.0291(5) Uani 1 1 d . . . . .
O1C O 0.7841(4) 0.54830(9) 0.7883(2) 0.0274(5) Uani 1 1 d . . . . .
O3C O 0.8451(4) 0.57499(10) 0.4390(2) 0.0337(6) Uani 1 1 d . . . . .
O3D O 0.3482(5) 0.42359(10) 0.8176(2) 0.0373(6) Uani 1 1 d . . . . .
N1A N 0.7499(5) 0.47329(11) 1.3429(3) 0.0241(6) Uani 1 1 d . . . . .
N1B N 0.2518(5) 0.52616(11) -0.0854(3) 0.0248(6) Uani 1 1 d . . . . .
C1A C 0.7828(5) 0.46318(12) 1.0250(3) 0.0219(6) Uani 1 1 d . . . . .
C1B C 0.2809(5) 0.53635(12) 0.2317(3) 0.0211(6) Uani 1 1 d . . . . .
C3D C 0.1860(5) 0.37191(13) 0.6563(3) 0.0269(7) Uani 1 1 d . . . . .
C3B C 0.3527(5) 0.60042(12) 0.0472(3) 0.0235(6) Uani 1 1 d . . . . .
C1D C 0.2708(5) 0.45839(12) 0.5973(3) 0.0239(7) Uani 1 1 d . . . . .
C1C C 0.7661(5) 0.54053(12) 0.6588(3) 0.0234(6) Uani 1 1 d . . . . .
C2C C 0.8285(5) 0.58561(12) 0.5769(3) 0.0257(7) Uani 1 1 d . . . . .
C5B C 0.3647(6) 0.65625(12) 0.0364(3) 0.0280(7) Uani 1 1 d . . . . .
C4C C 0.4645(5) 0.62031(15) 0.5245(3) 0.0308(7) Uani 1 1 d . . . . .
C2A C 0.7152(5) 0.41556(12) 1.0905(3) 0.0245(7) Uani 1 1 d . . . . .
C3A C 0.8496(5) 0.39906(12) 1.2115(3) 0.0221(6) Uani 1 1 d . . . . .
C4A C 0.7636(5) 0.41907(13) 1.3434(3) 0.0265(7) Uani 1 1 d . . . . .
C4B C 0.2673(5) 0.58047(13) -0.0861(3) 0.0271(7) Uani 1 1 d . . . . .
C2B C 0.2159(5) 0.58421(12) 0.1664(3) 0.0247(6) Uani 1 1 d . . . . .
C3C C 0.6595(5) 0.62512(12) 0.5922(3) 0.0251(6) Uani 1 1 d . . . . .
C5A C 0.8619(5) 0.34338(12) 1.2209(3) 0.0256(7) Uani 1 1 d . . . . .
C2D C 0.3419(5) 0.41369(13) 0.6784(3) 0.0279(7) Uani 1 1 d . . . . .
C5C C 0.3135(6) 0.65686(15) 0.5314(4) 0.0339(8) Uani 1 1 d . . . . .
C8C C 0.6975(6) 0.66618(14) 0.6696(4) 0.0324(8) Uani 1 1 d . . . . .
C4D C -0.0149(6) 0.37382(15) 0.7152(4) 0.0326(7) Uani 1 1 d . . . . .
C8D C 0.2415(7) 0.33109(15) 0.5835(4) 0.0365(8) Uani 1 1 d . . . . .
C6C C 0.3508(6) 0.69847(15) 0.6079(4) 0.0380(8) Uani 1 1 d . . . . .
C6A C 0.9826(6) 0.31812(14) 1.1073(4) 0.0354(8) Uani 1 1 d . . . . .
C6B C 0.4823(6) 0.68264(14) 0.1511(4) 0.0346(8) Uani 1 1 d . . . . .
C5D C -0.1558(7) 0.33515(15) 0.7024(4) 0.0380(8) Uani 1 1 d . . . . .
C6D C -0.0981(7) 0.29380(16) 0.6304(4) 0.0445(10) Uani 1 1 d . . . . .
C7C C 0.5426(7) 0.70262(15) 0.6776(4) 0.0417(9) Uani 1 1 d . . . . .
C7A C 0.9840(7) 0.26312(15) 1.1302(5) 0.0426(10) Uani 1 1 d . . . . .
C7D C 0.1008(8) 0.29176(17) 0.5707(4) 0.0471(10) Uani 1 1 d . . . . .
C8B C 0.7096(8) 0.66430(19) 0.1702(7) 0.0550(13) Uani 1 1 d . . . . .
C7B C 0.4800(8) 0.73751(16) 0.1241(5) 0.0458(10) Uani 1 1 d . . . . .
C8A C 1.2067(10) 0.3373(2) 1.0908(9) 0.070(2) Uani 1 1 d . . . . .
H8B H 0.219(6) 0.5188(14) -0.167(4) 0.018(9) Uiso 1 1 d . . . . .
H5C H 0.185(7) 0.6540(15) 0.484(4) 0.027(10) Uiso 1 1 d . . . . .
H2D H 0.465(10) 0.439(2) 0.841(6) 0.058(15) Uiso 1 1 d . . . . .
H3A H 1.000(7) 0.4092(15) 1.198(4) 0.025(10) Uiso 1 1 d . . . . .
H5D H -0.294(7) 0.3372(16) 0.743(4) 0.031(10) Uiso 1 1 d . . . . .
H3C H 0.970(6) 0.5976(14) 0.621(4) 0.020(9) Uiso 1 1 d . . . . .
H4D H -0.065(8) 0.4042(19) 0.760(5) 0.044(12) Uiso 1 1 d . . . . .
H4B H 0.370(8) 0.5899(19) -0.165(5) 0.051(14) Uiso 1 1 d . . . . .
H8C H 0.830(7) 0.6677(17) 0.716(5) 0.033(11) Uiso 1 1 d . . . . .
H5B H 0.125(7) 0.5961(15) -0.102(4) 0.028(10) Uiso 1 1 d . . . . .
H7B H 0.366(7) 0.5125(17) -0.045(5) 0.031(10) Uiso 1 1 d . . . . .
H1B H 0.227(7) 0.6066(18) 0.242(5) 0.038(11) Uiso 1 1 d . . . . .
H8D H 0.381(8) 0.3285(17) 0.544(5) 0.039(12) Uiso 1 1 d . . . . .
H6A H 0.713(6) 0.4805(15) 1.425(4) 0.019(9) Uiso 1 1 d . . . . .
H10B H 0.437(6) 0.6654(16) -0.054(4) 0.030(10) Uiso 1 1 d . . . . .
H9B H 0.219(8) 0.6690(18) 0.026(5) 0.039(12) Uiso 1 1 d . . . . .
H1A H 0.564(6) 0.4197(14) 1.117(4) 0.022(9) Uiso 1 1 d . . . . .
H5A H 0.860(6) 0.4099(14) 1.417(4) 0.019(9) Uiso 1 1 d . . . . .
H6D H -0.184(8) 0.264(2) 0.624(5) 0.045(13) Uiso 1 1 d . . . . .
H17B H 0.718(8) 0.630(2) 0.200(5) 0.055(14) Uiso 1 1 d . . . . .
H7C H 0.568(8) 0.732(2) 0.729(5) 0.051(13) Uiso 1 1 d . . . . .
H4A H 0.614(7) 0.4060(16) 1.364(4) 0.032(10) Uiso 1 1 d . . . . .
H7A H 0.641(7) 0.4838(18) 1.294(5) 0.036(11) Uiso 1 1 d . . . . .
H9A H 0.723(7) 0.3298(17) 1.225(4) 0.033(11) Uiso 1 1 d . . . . .
H10A H 0.936(7) 0.3343(17) 1.305(5) 0.037(11) Uiso 1 1 d . . . . .
H15B H 0.780(11) 0.684(3) 0.240(8) 0.09(2) Uiso 1 1 d . . . . .
H16B H 0.778(9) 0.662(2) 0.084(6) 0.058(16) Uiso 1 1 d . . . . .
H6C H 0.250(8) 0.726(2) 0.606(5) 0.051(14) Uiso 1 1 d . . . . .
H11B H 0.405(7) 0.6796(17) 0.241(5) 0.038(11) Uiso 1 1 d . . . . .
H3D H 0.490(6) 0.4041(13) 0.635(4) 0.018(8) Uiso 1 1 d . . . . .
H2B H 0.059(6) 0.5794(14) 0.137(4) 0.022(9) Uiso 1 1 d . . . . .
H13B H 0.333(8) 0.7508(18) 0.125(5) 0.038(12) Uiso 1 1 d . . . . .
H14A H 0.843(8) 0.2508(18) 1.137(5) 0.040(12) Uiso 1 1 d . . . . .
H14B H 0.557(10) 0.746(2) 0.032(7) 0.068(17) Uiso 1 1 d . . . . .
H12B H 0.558(9) 0.756(2) 0.200(6) 0.061(16) Uiso 1 1 d . . . . .
H7D H 0.155(8) 0.261(2) 0.523(5) 0.046(13) Uiso 1 1 d . . . . .
H13A H 1.054(8) 0.249(2) 1.054(6) 0.050(13) Uiso 1 1 d . . . . .
H8A H 0.863(7) 0.4882(16) 1.311(4) 0.025(9) Uiso 1 1 d . . . . .
H2A H 0.728(7) 0.3919(18) 1.025(5) 0.038(11) Uiso 1 1 d . . . . .
H12A H 1.056(9) 0.258(2) 1.222(6) 0.056(15) Uiso 1 1 d . . . . .
H1D H 0.245(9) 0.479(2) 0.421(6) 0.059(15) Uiso 1 1 d . . . . .
H17A H 1.205(10) 0.370(3) 1.075(6) 0.069(17) Uiso 1 1 d . . . . .
H15A H 1.265(7) 0.3317(16) 1.173(5) 0.024(12) Uiso 1 1 d . . . . .
H2C H 0.972(9) 0.559(2) 0.423(6) 0.055(15) Uiso 1 1 d . . . . .
H4C H 0.434(7) 0.5902(19) 0.479(5) 0.044(12) Uiso 1 1 d . . . . .
H1C H 0.737(13) 0.519(3) 0.834(8) 0.10(3) Uiso 1 1 d . . . . .
H16A H 1.298(13) 0.319(3) 1.031(8) 0.10(2) Uiso 1 1 d . . . . .
H3B H 0.510(7) 0.5875(16) 0.059(4) 0.032(10) Uiso 1 1 d . . . . .
H11A H 0.896(9) 0.324(2) 1.015(7) 0.066(16) Uiso 1 1 d . . . . .
H6B H 0.117(10) 0.513(2) -0.031(6) 0.065(16) 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
O1D C1D 1.313(4) . ?
O1D H1D 0.93(6) . ?
O2C C1C 1.215(4) . ?
O2B C1B 1.239(4) . ?
O2A C1A 1.235(4) . ?
O1A C1A 1.281(4) . ?
O1B C1B 1.286(4) . ?
O2D C1D 1.216(4) . ?
O1C C1C 1.311(4) . ?
O1C H1C 0.97(9) . ?
O3C C2C 1.409(4) . ?
O3C H2C 0.93(6) . ?
O3D C2D 1.414(4) . ?
O3D H2D 0.87(6) . ?
N1A C4A 1.488(5) . ?
N1A H6A 0.88(4) . ?
N1A H7A 0.88(5) . ?
N1A H8A 0.88(5) . ?
N1B C4B 1.491(5) . ?
N1B H8B 0.86(4) . ?
N1B H7B 0.90(5) . ?
N1B H6B 1.07(6) . ?
C1A C2A 1.520(4) . ?
C1B C2B 1.517(4) . ?
C3D C2D 1.517(5) . ?
C3D C4D 1.390(5) . ?
C3D C8D 1.378(5) . ?
C3B C5B 1.535(5) . ?
C3B C4B 1.528(4) . ?
C3B C2B 1.535(4) . ?
C3B H3B 1.05(4) . ?
C1D C2D 1.530(4) . ?
C1C C2C 1.532(4) . ?
C2C C3C 1.520(5) . ?
C2C H3C 1.03(4) . ?
C5B C6B 1.533(5) . ?
C5B H10B 1.05(4) . ?
C5B H9B 0.98(5) . ?
C4C C3C 1.394(5) . ?
C4C C5C 1.377(5) . ?
C4C H4C 0.96(5) . ?
C2A C3A 1.532(4) . ?
C2A H1A 0.99(4) . ?
C2A H2A 0.93(5) . ?
C3A C4A 1.525(4) . ?
C3A C5A 1.530(5) . ?
C3A H3A 0.99(4) . ?
C4A H5A 0.98(4) . ?
C4A H4A 1.02(5) . ?
C4B H4B 1.05(5) . ?
C4B H5B 1.00(4) . ?
C2B H1B 0.97(5) . ?
C2B H2B 1.03(4) . ?
C3C C8C 1.383(5) . ?
C5A C6A 1.530(5) . ?
C5A H9A 0.95(5) . ?
C5A H10A 0.99(5) . ?
C2D H3D 1.06(4) . ?
C5C C6C 1.389(6) . ?
C5C H5C 0.93(4) . ?
C8C C7C 1.393(6) . ?
C8C H8C 0.95(5) . ?
C4D C5D 1.383(6) . ?
C4D H4D 1.00(5) . ?
C8D C7D 1.396(6) . ?
C8D H8D 0.96(5) . ?
C6C C7C 1.385(6) . ?
C6C H6C 0.98(6) . ?
C6A C7A 1.524(5) . ?
C6A C8A 1.505(7) . ?
C6A H11A 1.08(6) . ?
C6B C8B 1.517(6) . ?
C6B C7B 1.527(6) . ?
C6B H11B 1.02(5) . ?
C5D C6D 1.389(7) . ?
C5D H5D 0.96(5) . ?
C6D C7D 1.383(7) . ?
C6D H6D 0.97(5) . ?
C7C H7C 0.96(6) . ?
C7A H14A 0.95(5) . ?
C7A H13A 0.96(6) . ?
C7A H12A 1.02(6) . ?
C7D H7D 1.02(5) . ?
C8B H17B 0.99(6) . ?
C8B H15B 0.98(8) . ?
C8B H16B 0.96(6) . ?
C7B H13B 0.99(5) . ?
C7B H14B 1.06(7) . ?
C7B H12B 1.02(6) . ?
C8A H17A 0.90(8) . ?
C8A H15A 0.91(4) . ?
C8A H16A 0.96(9) . ?

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
C1D O1D H1D 110(4) . . ?
C1C O1C H1C 108(5) . . ?
C2C O3C H2C 110(3) . . ?
C2D O3D H2D 112(4) . . ?
C4A N1A H6A 104(3) . . ?
C4A N1A H7A 112(3) . . ?
C4A N1A H8A 115(3) . . ?
H6A N1A H7A 104(4) . . ?
H6A N1A H8A 117(4) . . ?
H7A N1A H8A 105(4) . . ?
C4B N1B H8B 104(3) . . ?
C4B N1B H7B 111(3) . . ?
C4B N1B H6B 113(3) . . ?
H8B N1B H7B 121(4) . . ?
H8B N1B H6B 103(4) . . ?
H7B N1B H6B 105(4) . . ?
O2A C1A O1A 124.1(3) . . ?
O2A C1A C2A 120.7(3) . . ?
O1A C1A C2A 115.2(3) . . ?
O2B C1B O1B 123.9(3) . . ?
O2B C1B C2B 120.7(3) . . ?
O1B C1B C2B 115.4(3) . . ?
C4D C3D C2D 119.4(3) . . ?
C8D C3D C2D 121.6(3) . . ?
C8D C3D C4D 119.0(3) . . ?
C5B C3B H3B 107(2) . . ?
C4B C3B C5B 108.2(3) . . ?
C4B C3B C2B 112.1(3) . . ?
C4B C3B H3B 107(2) . . ?
C2B C3B C5B 111.7(3) . . ?
C2B C3B H3B 110(2) . . ?
O1D C1D C2D 111.8(3) . . ?
O2D C1D O1D 124.1(3) . . ?
O2D C1D C2D 124.1(3) . . ?
O2C C1C O1C 124.1(3) . . ?
O2C C1C C2C 123.9(3) . . ?
O1C C1C C2C 111.9(3) . . ?
O3C C2C C1C 112.0(3) . . ?
O3C C2C C3C 107.5(3) . . ?
O3C C2C H3C 114(2) . . ?
C1C C2C H3C 105(2) . . ?
C3C C2C C1C 109.9(3) . . ?
C3C C2C H3C 109(2) . . ?
C3B C5B H10B 109(2) . . ?
C3B C5B H9B 109(3) . . ?
C6B C5B C3B 116.2(3) . . ?
C6B C5B H10B 109(2) . . ?
C6B C5B H9B 111(3) . . ?
H10B C5B H9B 103(4) . . ?
C3C C4C H4C 119(3) . . ?
C5C C4C C3C 120.2(4) . . ?
C5C C4C H4C 121(3) . . ?
C1A C2A C3A 116.0(3) . . ?
C1A C2A H1A 107(2) . . ?
C1A C2A H2A 106(3) . . ?
C3A C2A H1A 110(2) . . ?
C3A C2A H2A 107(3) . . ?
H1A C2A H2A 111(4) . . ?
C2A C3A H3A 109(2) . . ?
C4A C3A C2A 112.2(3) . . ?
C4A C3A C5A 108.9(3) . . ?
C4A C3A H3A 111(2) . . ?
C5A C3A C2A 111.7(3) . . ?
C5A C3A H3A 104(2) . . ?
N1A C4A C3A 112.1(3) . . ?
N1A C4A H5A 107(2) . . ?
N1A C4A H4A 107(2) . . ?
C3A C4A H5A 110(2) . . ?
C3A C4A H4A 112(2) . . ?
H5A C4A H4A 109(3) . . ?
N1B C4B C3B 112.0(3) . . ?
N1B C4B H4B 107(3) . . ?
N1B C4B H5B 112(2) . . ?
C3B C4B H4B 111(3) . . ?
C3B C4B H5B 107(2) . . ?
H4B C4B H5B 109(4) . . ?
C1B C2B C3B 115.7(3) . . ?
C1B C2B H1B 101(3) . . ?
C1B C2B H2B 105(2) . . ?
C3B C2B H1B 112(3) . . ?
C3B C2B H2B 111(2) . . ?
H1B C2B H2B 111(3) . . ?
C4C C3C C2C 119.3(3) . . ?
C8C C3C C2C 121.2(3) . . ?
C8C C3C C4C 119.5(3) . . ?
C3A C5A C6A 115.5(3) . . ?
C3A C5A H9A 110(3) . . ?
C3A C5A H10A 109(3) . . ?
C6A C5A H9A 108(3) . . ?
C6A C5A H10A 106(3) . . ?
H9A C5A H10A 107(4) . . ?
O3D C2D C3D 107.4(3) . . ?
O3D C2D C1D 111.7(3) . . ?
O3D C2D H3D 115(2) . . ?
C3D C2D C1D 110.1(3) . . ?
C3D C2D H3D 108(2) . . ?
C1D C2D H3D 104(2) . . ?
C4C C5C C6C 120.8(4) . . ?
C4C C5C H5C 120(3) . . ?
C6C C5C H5C 119(3) . . ?
C3C C8C C7C 119.9(3) . . ?
C3C C8C H8C 117(3) . . ?
C7C C8C H8C 123(3) . . ?
C3D C4D H4D 121(3) . . ?
C5D C4D C3D 120.5(4) . . ?
C5D C4D H4D 119(3) . . ?
C3D C8D C7D 120.9(4) . . ?
C3D C8D H8D 121(3) . . ?
C7D C8D H8D 119(3) . . ?
C5C C6C H6C 121(3) . . ?
C7C C6C C5C 118.9(4) . . ?
C7C C6C H6C 120(3) . . ?
C5A C6A H11A 109(3) . . ?
C7A C6A C5A 109.8(3) . . ?
C7A C6A H11A 106(3) . . ?
C8A C6A C5A 112.8(4) . . ?
C8A C6A C7A 110.9(4) . . ?
C8A C6A H11A 108(3) . . ?
C5B C6B H11B 113(3) . . ?
C8B C6B C5B 112.3(4) . . ?
C8B C6B C7B 110.8(4) . . ?
C8B C6B H11B 108(3) . . ?
C7B C6B C5B 109.2(3) . . ?
C7B C6B H11B 103(3) . . ?
C4D C5D C6D 120.3(4) . . ?
C4D C5D H5D 119(3) . . ?
C6D C5D H5D 120(3) . . ?
C5D C6D H6D 125(3) . . ?
C7D C6D C5D 119.5(4) . . ?
C7D C6D H6D 116(3) . . ?
C8C C7C H7C 121(3) . . ?
C6C C7C C8C 120.7(4) . . ?
C6C C7C H7C 118(3) . . ?
C6A C7A H14A 111(3) . . ?
C6A C7A H13A 106(3) . . ?
C6A C7A H12A 106(3) . . ?
H14A C7A H13A 110(4) . . ?
H14A C7A H12A 107(4) . . ?
H13A C7A H12A 117(4) . . ?
C8D C7D H7D 118(3) . . ?
C6D C7D C8D 119.8(4) . . ?
C6D C7D H7D 122(3) . . ?
C6B C8B H17B 114(3) . . ?
C6B C8B H15B 109(4) . . ?
C6B C8B H16B 110(3) . . ?
H17B C8B H15B 107(5) . . ?
H17B C8B H16B 99(5) . . ?
H15B C8B H16B 118(5) . . ?
C6B C7B H13B 112(3) . . ?
C6B C7B H14B 111(4) . . ?
C6B C7B H12B 110(3) . . ?
H13B C7B H14B 111(4) . . ?
H13B C7B H12B 105(4) . . ?
H14B C7B H12B 109(5) . . ?
C6A C8A H17A 111(4) . . ?
C6A C8A H15A 102(3) . . ?
C6A C8A H16A 116(5) . . ?
H17A C8A H15A 109(5) . . ?
H17A C8A H16A 114(6) . . ?
H15A C8A H16A 104(6) . . ?

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
O1D C1D C2D O3D 173.4(3) . . . . ?
O1D C1D C2D C3D -67.3(3) . . . . ?
O2C C1C C2C O3C -10.5(4) . . . . ?
O2C C1C C2C C3C 109.0(3) . . . . ?
O2B C1B C2B C3B -5.4(4) . . . . ?
O2A C1A C2A C3A -4.7(5) . . . . ?
O1A C1A C2A C3A 174.2(3) . . . . ?
O1B C1B C2B C3B 173.6(3) . . . . ?
O2D C1D C2D O3D -7.0(4) . . . . ?
O2D C1D C2D C3D 112.3(4) . . . . ?
O1C C1C C2C O3C 169.8(3) . . . . ?
O1C C1C C2C C3C -70.8(3) . . . . ?
O3C C2C C3C C4C 47.0(4) . . . . ?
O3C C2C C3C C8C -131.6(3) . . . . ?
C1A C2A C3A C4A 89.8(3) . . . . ?
C1A C2A C3A C5A -147.7(3) . . . . ?
C3D C4D C5D C6D 0.1(6) . . . . ?
C3D C8D C7D C6D 0.7(6) . . . . ?
C3B C5B C6B C8B 56.4(5) . . . . ?
C3B C5B C6B C7B 179.7(3) . . . . ?
C1C C2C C3C C4C -75.2(4) . . . . ?
C1C C2C C3C C8C 106.2(4) . . . . ?
C2C C3C C8C C7C 177.6(3) . . . . ?
C5B C3B C4B N1B 179.5(3) . . . . ?
C5B C3B C2B C1B -149.0(3) . . . . ?
C4C C3C C8C C7C -1.0(5) . . . . ?
C4C C5C C6C C7C -0.2(6) . . . . ?
C2A C3A C4A N1A -56.7(4) . . . . ?
C2A C3A C5A C6A 66.3(4) . . . . ?
C3A C5A C6A C7A 179.5(3) . . . . ?
C3A C5A C6A C8A 55.2(5) . . . . ?
C4A C3A C5A C6A -169.3(3) . . . . ?
C4B C3B C5B C6B -169.9(3) . . . . ?
C4B C3B C2B C1B 89.4(3) . . . . ?
C2B C3B C5B C6B 66.1(4) . . . . ?
C2B C3B C4B N1B -56.8(4) . . . . ?
C3C C4C C5C C6C -1.4(5) . . . . ?
C3C C8C C7C C6C -0.6(6) . . . . ?
C5A C3A C4A N1A 179.1(3) . . . . ?
C2D C3D C4D C5D -176.7(3) . . . . ?
C2D C3D C8D C7D 176.2(3) . . . . ?
C5C C4C C3C C2C -176.6(3) . . . . ?
C5C C4C C3C C8C 2.0(5) . . . . ?
C5C C6C C7C C8C 1.2(6) . . . . ?
C4D C3D C2D O3D 48.5(4) . . . . ?
C4D C3D C2D C1D -73.3(4) . . . . ?
C4D C3D C8D C7D -1.1(5) . . . . ?
C4D C5D C6D C7D -0.6(6) . . . . ?
C8D C3D C2D O3D -128.8(3) . . . . ?
C8D C3D C2D C1D 109.3(4) . . . . ?
C8D C3D C4D C5D 0.7(5) . . . . ?
C5D C6D C7D C8D 0.2(6) . . . . ?

_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
####################################################################### 
# 
# 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_R-PGB_R-MAN
_database_code_depnum_ccdc_archive 'CCDC 2170107'
loop_
_audit_author_name
_audit_author_address
'Daniel Komisarek'
;Heinrich Heine University Duesseldorf
Germany
;
_audit_update_record             
;
2022-05-03 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_date             2021-09-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_name_common            '(R)-Pregabalin (R)-Mandelic Acid'
_chemical_name_systematic        
'(R)-3-isobutyl-Î³-aminobutyric acid (R)-2-Hydroxy-2-phenylacetic acid'
_chemical_formula_moiety         'C8 H17 N O2, C8 H8 O3'
_chemical_formula_sum            'C16 H25 N O5'
_chemical_formula_weight         311.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H17 N O2 C8 H8 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.25270(10)
_cell_length_b                   27.3848(3)
_cell_length_c                   9.96030(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.4830(10)
_cell_angle_gamma                90
_cell_volume                     1705.43(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    33130
_cell_measurement_temperature    99.97(16)
_cell_measurement_theta_max      77.3600
_cell_measurement_theta_min      3.2050
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.757
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.458
_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_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -6 0.0448
4 3 0 0.2050
-4 -3 1 0.1704
0 -1 6 0.0522
0 -3 -6 0.0538
0 -18 1 0.0787
0 18 1 0.0019
-2 -16 0 0.1084
3 -9 0 0.1901

_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.1438 1.2159 -6.4475 0.0100 0.0311 -0.9995
4.0005 2.9497 0.0650 -0.2325 -0.9726 0.0091
-3.9428 -3.1387 1.0651 0.2288 0.9592 0.1661
-0.0228 -1.3399 6.4504 -0.0003 0.0094 1.0000
-0.0609 -2.9023 -6.3806 -0.2100 0.1026 -0.9723
-0.1598 -17.5335 1.0234 -0.8795 0.4178 0.2281
0.1695 17.6980 0.5191 0.9030 -0.4296 0.0091
-1.7991 -15.9283 0.0025 -0.6492 0.7583 0.0597
3.4259 -9.4814 -0.3681 -0.8235 -0.5672 -0.0091

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       7
_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       -10
_diffrn_reflns_number            47481
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.749
_diffrn_reflns_theta_min         3.228
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(16)
_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 0.939
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00  85.00   0.50    0.11    --   49.27  19.00 150.00   74
  2  ω     44.00  77.00   0.50    0.11    --   66.00  77.00  93.24   66
  3  ω     41.00  66.00   0.50    0.11    --   62.00  77.00  -1.48   50
  4  ω     41.00  66.00   0.50    0.11    --   62.00  77.00 -33.85   50
  5  ω    -72.00 -20.00   0.50    0.44    --  -90.00  77.00  30.00  104
  6  ω    -54.00 -28.00   0.50    0.44    --  -90.00  57.00  30.00   52
  7  ω    -70.00 -24.00   0.50    0.44    --  -90.00  57.00 150.00   92
  8  ω   -107.00 -76.00   0.50    0.44    --  -90.00  77.00  30.00   62
  9  ω    -46.00 -20.00   0.50    0.44    --  -90.00  38.00 -30.00   52
 10  ω    -47.00 -21.00   0.50    0.44    --  -90.00  38.00 -60.00   52
 11  ω    -71.00 -22.00   0.50    0.44    --  -90.00  57.00-120.00   98
 12  ω     15.00  40.00   0.50    0.11    --   42.00  89.00 173.01   50
 13  ω    -54.00 -29.00   0.50    0.11    --   10.00 154.00 179.88   50
 14  ω    -15.00  14.00   0.50    0.11    --   18.00 101.00  22.11   58
 15  ω     -1.00  24.00   0.50    0.11    --   30.00  96.00  19.77   50
 16  ω     14.00  39.00   0.50    0.11    --   42.00  91.00  14.46   50
 17  ω     -2.00  25.00   0.50    0.11    --   30.00  98.00-164.21   54
 18  ω    -75.00 -49.00   0.50    0.11    --  -49.27 146.00-177.00   52
 19  ω    -63.00 -36.00   0.50    0.44    --  -90.00 125.00  16.00   54
 20  ω    -73.00 -48.00   0.50    0.11    --  -49.27 125.00  16.00   50
 21  ω    -51.00 -19.00   0.50    0.11    --   -2.00 134.00  79.15   64
 22  ω    -53.00 -28.00   0.50    0.11    --  -49.27 -77.00 -60.00   50
 23  ω    -70.00 -28.00   0.50    0.11    --  -49.27 -77.00-120.00   84
 24  ω   -106.00 -77.00   0.50    0.11    --  -49.27 -77.00 -60.00   58
 25  ω    -54.00 -28.00   0.50    0.11    --  -49.27 -77.00 120.00   52
 26  ω    -53.00 -28.00   0.50    0.11    --  -49.27 -77.00  90.00   50
 27  ω    -54.00 -28.00   0.50    0.11    --  -49.27 -77.00  60.00   52
 28  ω    -56.00 -28.00   0.50    0.11    --  -49.27 -77.00  30.00   56
 29  ω   -110.00 -84.00   0.50    0.11    --  -49.27 -77.00 120.00   52
 30  ω    -56.00 -30.00   0.50    0.11    --  -49.27 -77.00   0.00   52
 31  ω    -76.00 -38.00   0.50    0.11    --  -49.27 -19.00 -30.00   76
 32  ω    -53.00 -28.00   0.50    0.11    --  -49.27 -77.00 -90.00   50
 33  ω    -54.00 -28.00   0.50    0.11    --  -49.27 -77.00-150.00   52
 34  ω    -63.00 -28.00   0.50    0.11    --  -49.27 -77.00-180.00   70
 35  ω    -83.00 -48.00   0.50    0.44    --  -70.00 -77.00-159.98   70
 36  ω   -103.00 -69.00   0.50    0.44    --  -90.00 -77.00   0.00   68
 37  ω   -159.00 -68.00   0.50    0.44    --  -90.00 -77.00 -30.00  182
 38  ω   -159.00-129.00   0.50    0.44    --  -90.00 -77.00 150.00   60
 39  ω   -140.00 -64.00   0.50    0.44    --  -86.00 -77.00 135.64  152
 40  ω   -105.00 -68.00   0.50    0.44    --  -90.00 -77.00 150.00   74
 41  ω    -95.00 -68.00   0.50    0.44    --  -90.00 -77.00  53.61   54
 42  ω    -93.00 -68.00   0.50    0.44    --  -90.00 -77.00  60.00   50
 43  ω   -121.00 -72.00   0.50    0.44    --  -90.00 -77.00 120.00   98
 44  ω   -153.00-127.00   0.50    0.44    --  -90.00 -77.00 120.00   52
 45  ω   -147.00 -98.00   0.50    0.44    --  -90.00 -77.00  60.00   98
 46  ω    -93.00 -68.00   0.50    0.44    --  -90.00 -77.00-150.00   50
 47  ω    -96.00 -69.00   0.50    0.44    --  -90.00 -77.00-180.00   54
 48  ω    -95.00 -68.00   0.50    0.44    --  -90.00 -77.00-170.52   54
 49  ω   -161.00-105.00   0.50    0.44    --  -90.00 -77.00-170.52  112
 50  ω   -156.00-116.00   0.50    0.44    --  -90.00 -77.00-180.00   80
 51  ω   -130.00-104.00   0.50    0.44    --  -90.00 -77.00-150.00   52
 52  ω   -102.00 -65.00   0.50    0.44    --  -86.00 -76.00-139.52   74
 53  ω   -158.00-107.00   0.50    0.44    --  -86.00 -76.00-139.52  102
 54  ω    -67.00 -41.00   0.50    0.11    --  -62.00 -74.00 -19.16   52
 55  ω    -95.00 -69.00   0.50    0.44    --  -90.00 -75.00  45.15   52
 56  ω    -84.00 -57.00   0.50    0.44    --  -78.00 -74.00  64.26   54
 57  ω   -122.00 -69.00   0.50    0.44    --  -90.00 -76.00  97.16  106
 58  ω   -145.00-119.00   0.50    0.44    --  -90.00 -74.00 160.12   52
 59  ω   -100.00 -69.00   0.50    0.44    --  -90.00 -74.00 160.12   62
 60  ω   -160.00-104.00   0.50    0.44    --  -90.00 -77.00  53.61  112
 61  ω   -143.00-117.00   0.50    0.44    --  -78.00 -73.00-101.52   52
 62  ω    -83.00 -57.00   0.50    0.44    --  -78.00 -74.00-127.15   52
 63  ω    -84.00 -58.00   0.50    0.44    --  -78.00 -73.00-118.26   52
 64  ω    -84.00 -58.00   0.50    0.44    --  -78.00 -73.00-109.60   52
 65  ω    -84.00 -58.00   0.50    0.44    --  -78.00 -73.00-101.52   52
 66  ω   -131.00 -70.00   0.50    0.44    --  -90.00 -73.00 -76.08  122
 67  ω   -161.00 -70.00   0.50    0.44    --  -90.00 -72.00 -55.80  182
 68  ω   -101.00 -70.00   0.50    0.44    --  -90.00 -72.00  16.82   62
 69  ω    -85.00 -58.00   0.50    0.44    --  -78.00 -72.00  40.42   54
 70  ω    -84.00 -58.00   0.50    0.44    --  -78.00 -72.00  48.50   52
 71  ω    -88.00 -62.00   0.50    0.44    --  -82.00 -73.00  76.40   52
 72  ω   -161.00-115.00   0.50    0.44    --  -90.00 -72.00  16.82   92
 73  ω   -160.00 -70.00   0.50    0.44    --  -90.00 -72.00   8.10  180
 74  ω   -145.00 -71.00   0.50    0.44    --  -90.00 -71.00 -23.08  148
 75  ω   -135.00-110.00   0.50    0.11    --  -66.00 -71.00-105.47   50
 76  ω    -72.00 -47.00   0.50    0.11    --  -66.00 -71.00-105.47   50
 77  ω    -78.00 -52.00   0.50    0.44    --  -70.00 -68.00 -71.40   52
 78  ω    -87.00 -56.00   0.50    0.44    --  -74.00 -67.00 -89.60   62
 79  ω    -79.00 -52.00   0.50    0.44    --  -70.00 -67.00 -49.60   54
 80  ω    -89.00 -56.00   0.50    0.44    --  -74.00 -67.00 -22.03   66
 81  ω    -78.00 -47.00   0.50    0.11    --  -66.00 -71.00  10.04   62
 82  ω    -78.00 -52.00   0.50    0.44    --  -70.00 -68.00  -1.95   52
 83  ω    -70.00 -44.00   0.50    0.11    --  -62.00 -67.00 127.18   52
 84  ω    -73.00 -46.00   0.50    0.11    --  -62.00 -66.00 152.70   54
 85  ω    -74.00 -49.00   0.50    0.11    --  -66.00 -65.00 104.58   50
 86  ω    -70.00 -45.00   0.50    0.11    --  -62.00 -65.00  72.38   50
 87  ω    -86.00 -59.00   0.50    0.44    --  -74.00 -63.00 136.29   54
 88  ω   -134.00-108.00   0.50    0.11    --  -66.00 -65.00 104.58   52
 89  ω    -71.00 -45.00   0.50    0.11    --  -62.00 -65.00-177.61   52
 90  ω   -136.00 -79.00   0.50    0.44    --  -90.00-125.00 -90.00  114
 91  ω   -128.00 -84.00   0.50    0.44    --  -90.00-125.00 -61.00   88
 92  ω   -112.00 -86.00   0.50    0.11    --  -49.27-125.00 -61.00   52
 93  ω   -141.00 -70.00   0.50    0.44    --  -90.00-146.00 132.00  142
 94  ω    -90.00 -65.00   0.50    0.11    --  -49.27-146.00 132.00   50
 95  ω     39.00  79.00   0.50    0.44    --  109.41 -77.00 120.00   80
 96  ω    101.00 126.00   0.50    0.44    --  109.41 146.00-177.00   50
 97  ω    136.00 161.00   0.50    0.44    --  109.41 125.00  16.00   50
 98  ω     40.00  97.00   0.50    0.44    --  109.41 -77.00-120.00  114
 99  ω     38.00  77.00   0.50    0.44    --  109.41 -77.00 -60.00   78
100  ω     48.00 100.00   0.50    0.44    --  109.41 -77.00 -30.00  104
101  ω     48.00  85.00   0.50    0.11    --   49.27-146.00 132.00   74
102  ω     54.00  90.00   0.50    0.44    --  109.41-146.00 132.00   72
103  ω     97.00 127.00   0.50    0.44    --  109.41-146.00 132.00   60
104  ω     61.00 111.00   0.50    0.44    --  109.41-125.00 120.00  100
105  ω     85.00 111.00   0.50    0.44    --  109.41-125.00 -61.00   52
106  ω     86.00 112.00   0.50    0.44    --  109.41-125.00-120.00   52
107  ω     47.00  72.00   0.50    0.44    --  109.41-125.00-120.00   50
108  ω     39.00  64.00   0.50    0.44    --  109.41 -99.00-180.00   50
109  ω     70.00  96.00   0.50    0.44    --  109.41 -99.00-180.00   52
110  ω     35.00  96.00   0.50    0.11    --   49.27-125.00 -61.00  122
111  ω     69.00  98.00   0.50    0.44    --  109.41 -99.00 150.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0963555000
_diffrn_orient_matrix_UB_12      0.0516403000
_diffrn_orient_matrix_UB_13      0.0103417000
_diffrn_orient_matrix_UB_21      -0.2268312000
_diffrn_orient_matrix_UB_22      -0.0219875000
_diffrn_orient_matrix_UB_23      -0.0039086000
_diffrn_orient_matrix_UB_31      0.0027419000
_diffrn_orient_matrix_UB_32      -0.0040347000
_diffrn_orient_matrix_UB_33      0.1541931000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                6330
_reflns_number_total             6627
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 2902 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         6627
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.035
_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/[σ²(Fo²)+(0.0372P)²+0.1974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0689
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1B O 0.1808(2) 0.47466(5) 0.33884(13) 0.0280(3) Uani 1 1 d . . . . .
O2C O 0.7089(2) 0.49800(5) 0.60879(14) 0.0288(3) Uani 1 1 d . . . . .
O1D O 0.2880(2) 0.54909(5) 0.46782(14) 0.0289(3) Uani 1 1 d . . . . .
O2A O 0.9305(2) 0.51214(5) 1.07357(13) 0.0288(3) Uani 1 1 d . . . . .
O2B O 0.4264(2) 0.48898(5) 0.18298(13) 0.0286(3) Uani 1 1 d . . . . .
O1A O 0.6820(2) 0.52581(5) 0.91692(13) 0.0293(3) Uani 1 1 d . . . . .
O2D O 0.2091(2) 0.50360(5) 0.64707(14) 0.0301(3) Uani 1 1 d . . . . .
O1C O 0.7853(2) 0.45175(5) 0.78780(14) 0.0288(3) Uani 1 1 d . . . . .
O3C O 0.8462(3) 0.42492(6) 0.43891(15) 0.0347(3) Uani 1 1 d . . . . .
O3D O 0.3492(3) 0.57628(6) 0.81715(15) 0.0397(4) Uani 1 1 d . . . . .
N1B N 0.2534(3) 0.47378(6) -0.08547(18) 0.0264(3) Uani 1 1 d . . . . .
N1A N 0.7517(3) 0.52667(6) 1.34202(17) 0.0258(3) Uani 1 1 d . . . . .
C1A C 0.7840(3) 0.53709(7) 1.02439(18) 0.0232(4) Uani 1 1 d . . . . .
C1B C 0.2821(3) 0.46352(7) 0.23146(18) 0.0227(4) Uani 1 1 d . . . . .
C1C C 0.7682(3) 0.45971(7) 0.65831(19) 0.0245(4) Uani 1 1 d . . . . .
C3D C 0.1882(3) 0.62809(8) 0.6556(2) 0.0293(4) Uani 1 1 d . . . . .
C2A C 0.7152(3) 0.58438(7) 1.0903(2) 0.0262(4) Uani 1 1 d . . . . .
C1D C 0.2725(3) 0.54151(7) 0.59704(19) 0.0253(4) Uani 1 1 d . . . . .
C3C C 0.6604(3) 0.37500(7) 0.59219(19) 0.0256(4) Uani 1 1 d . . . . .
C2C C 0.8291(3) 0.41445(7) 0.5770(2) 0.0266(4) Uani 1 1 d . . . . .
C3B C 0.3525(3) 0.39957(7) 0.04696(19) 0.0262(4) Uani 1 1 d . . . . .
C4C C 0.4658(3) 0.37971(8) 0.5244(2) 0.0321(4) Uani 1 1 d . . . . .
C2B C 0.2156(3) 0.41590(7) 0.1660(2) 0.0267(4) Uani 1 1 d . . . . .
C5C C 0.3130(4) 0.34315(9) 0.5318(2) 0.0355(5) Uani 1 1 d . . . . .
C5B C 0.3652(4) 0.34380(7) 0.0365(2) 0.0320(4) Uani 1 1 d . . . . .
C4B C 0.2676(3) 0.41942(8) -0.0862(2) 0.0294(4) Uani 1 1 d . . . . .
C3A C 0.8505(3) 0.60102(7) 1.21104(19) 0.0252(4) Uani 1 1 d . . . . .
C4A C 0.7648(3) 0.58102(7) 1.3430(2) 0.0274(4) Uani 1 1 d . . . . .
C8D C 0.2452(4) 0.66903(9) 0.5824(2) 0.0385(5) Uani 1 1 d . . . . .
C2D C 0.3430(3) 0.58624(8) 0.6779(2) 0.0296(4) Uani 1 1 d . . . . .
C5A C 0.8635(3) 0.65660(8) 1.2211(2) 0.0293(4) Uani 1 1 d . . . . .
C4D C -0.0137(4) 0.62631(8) 0.7141(2) 0.0344(4) Uani 1 1 d . . . . .
C8C C 0.6974(4) 0.33395(8) 0.6702(2) 0.0347(5) Uani 1 1 d . . . . .
C6C C 0.3516(4) 0.30187(8) 0.6085(2) 0.0382(5) Uani 1 1 d . . . . .
C6A C 0.9836(4) 0.68173(8) 1.1072(3) 0.0386(5) Uani 1 1 d . . . . .
C6B C 0.4826(4) 0.31729(8) 0.1511(2) 0.0378(5) Uani 1 1 d . . . . .
C5D C -0.1543(4) 0.66517(9) 0.7008(2) 0.0402(5) Uani 1 1 d . . . . .
C6D C -0.0954(5) 0.70622(9) 0.6288(3) 0.0466(6) Uani 1 1 d . . . . .
C7D C 0.1035(5) 0.70810(9) 0.5692(3) 0.0491(6) Uani 1 1 d . . . . .
C7C C 0.5423(4) 0.29766(9) 0.6788(3) 0.0431(5) Uani 1 1 d . . . . .
C7A C 0.9841(4) 0.73681(9) 1.1302(3) 0.0459(6) Uani 1 1 d . . . . .
C7B C 0.4798(5) 0.26262(10) 0.1251(3) 0.0502(6) Uani 1 1 d . . . . .
C8B C 0.7102(5) 0.33555(12) 0.1709(4) 0.0626(9) Uani 1 1 d . . . . .
C8A C 1.2090(6) 0.66261(13) 1.0911(6) 0.0774(14) Uani 1 1 d . . . . .
H3B H 0.506(4) 0.4125(9) 0.058(2) 0.030(6) Uiso 1 1 d . . . . .
H15B H 0.789(5) 0.3173(12) 0.230(3) 0.055(8) Uiso 1 1 d . . . . .
H17A H 1.298(7) 0.6800(16) 1.038(5) 0.094(14) Uiso 1 1 d . . . . .
H4B H 0.362(4) 0.4089(9) -0.162(3) 0.036(6) Uiso 1 1 d . . . . .
H9B H 0.439(4) 0.3346(9) -0.052(3) 0.038(6) Uiso 1 1 d . . . . .
H3A H 0.997(4) 0.5893(8) 1.202(2) 0.022(5) Uiso 1 1 d . . . . .
H10B H 0.211(5) 0.3303(11) 0.028(3) 0.043(7) Uiso 1 1 d . . . . .
H8C H 0.836(4) 0.3314(10) 0.720(3) 0.039(7) Uiso 1 1 d . . . . .
H4D H -0.061(4) 0.5955(10) 0.767(3) 0.043(7) Uiso 1 1 d . . . . .
H2A H 0.565(4) 0.5810(9) 1.118(3) 0.034(6) Uiso 1 1 d . . . . .
H3D H 0.487(4) 0.5956(9) 0.640(2) 0.029(6) Uiso 1 1 d . . . . .
H5C H 0.179(5) 0.3456(10) 0.483(3) 0.043(7) Uiso 1 1 d . . . . .
H1B H 0.228(4) 0.3927(10) 0.240(3) 0.041(7) Uiso 1 1 d . . . . .
H10A H 0.716(4) 0.6711(10) 1.225(3) 0.039(7) Uiso 1 1 d . . . . .
H2B H 0.058(4) 0.4194(9) 0.136(2) 0.036(6) Uiso 1 1 d . . . . .
H8D H 0.387(4) 0.6711(9) 0.543(3) 0.036(6) Uiso 1 1 d . . . . .
H1A H 0.726(4) 0.6084(10) 1.021(3) 0.037(6) Uiso 1 1 d . . . . .
H2C H 0.962(4) 0.4018(8) 0.618(2) 0.025(5) Uiso 1 1 d . . . . .
H5A H 0.860(4) 0.5899(9) 1.414(2) 0.028(6) Uiso 1 1 d . . . . .
H16B H 0.717(5) 0.3716(14) 0.206(3) 0.067(9) Uiso 1 1 d . . . . .
H14B H 0.337(5) 0.2503(12) 0.121(3) 0.057(9) Uiso 1 1 d . . . . .
H6C H 0.246(5) 0.2762(11) 0.612(3) 0.046(7) Uiso 1 1 d . . . . .
H3C H 0.961(5) 0.4387(12) 0.419(3) 0.053(8) Uiso 1 1 d . . . . .
H12B H 0.559(5) 0.2440(11) 0.200(3) 0.056(8) Uiso 1 1 d . . . . .
H4A H 0.622(4) 0.5948(9) 1.363(3) 0.036(6) Uiso 1 1 d . . . . .
H6B H 0.137(5) 0.4864(11) -0.034(3) 0.048(7) Uiso 1 1 d . . . . .
H12A H 0.844(5) 0.7495(11) 1.140(3) 0.050(8) Uiso 1 1 d . . . . .
H11B H 0.403(5) 0.3218(12) 0.236(3) 0.062(9) Uiso 1 1 d . . . . .
H13A H 1.057(5) 0.7535(12) 1.054(3) 0.054(8) Uiso 1 1 d . . . . .
H7B H 0.373(5) 0.4876(10) -0.049(3) 0.039(7) Uiso 1 1 d . . . . .
H5B H 0.125(4) 0.4053(9) -0.108(2) 0.032(6) Uiso 1 1 d . . . . .
H7D H 0.148(5) 0.7386(12) 0.522(3) 0.056(8) Uiso 1 1 d . . . . .
H2D H 0.470(6) 0.5609(13) 0.838(4) 0.066(10) Uiso 1 1 d . . . . .
H11A H 0.906(5) 0.6748(11) 1.020(4) 0.060(9) Uiso 1 1 d . . . . .
H7A H 0.633(5) 0.5166(11) 1.283(3) 0.051(8) Uiso 1 1 d . . . . .
H13B H 0.560(7) 0.2550(15) 0.034(4) 0.087(12) Uiso 1 1 d . . . . .
H9A H 0.939(4) 0.6659(9) 1.305(3) 0.034(6) Uiso 1 1 d . . . . .
H6A H 0.731(4) 0.5143(11) 1.426(3) 0.042(7) Uiso 1 1 d . . . . .
H15A H 1.211(6) 0.6292(17) 1.070(4) 0.081(11) Uiso 1 1 d . . . . .
H8A H 0.863(4) 0.5126(10) 1.307(3) 0.034(6) Uiso 1 1 d . . . . .
H5D H -0.305(5) 0.6631(11) 0.745(3) 0.051(8) Uiso 1 1 d . . . . .
H14A H 1.057(6) 0.7453(12) 1.223(4) 0.067(10) Uiso 1 1 d . . . . .
H4C H 0.442(4) 0.4087(10) 0.473(3) 0.037(6) Uiso 1 1 d . . . . .
H8B H 0.243(4) 0.4862(10) -0.167(3) 0.039(7) Uiso 1 1 d . . . . .
H7C H 0.568(5) 0.2696(12) 0.733(3) 0.058(8) Uiso 1 1 d . . . . .
H6D H -0.192(6) 0.7356(13) 0.621(4) 0.069(10) Uiso 1 1 d . . . . .
H16A H 1.264(4) 0.6706(10) 1.177(3) 0.031(7) Uiso 1 1 d . . . . .
H17B H 0.786(6) 0.3342(13) 0.078(4) 0.066(10) Uiso 1 1 d . . . . .
H1D H 0.253(5) 0.5212(13) 0.422(3) 0.056(8) Uiso 1 1 d . . . . .
H1C H 0.748(6) 0.4822(13) 0.831(4) 0.069(10) 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
O1B C1B 1.284(2) . ?
O2C C1C 1.215(2) . ?
O1D C1D 1.308(2) . ?
O1D H1D 0.91(3) . ?
O2A C1A 1.240(2) . ?
O2B C1B 1.241(2) . ?
O1A C1A 1.279(2) . ?
O2D C1D 1.219(2) . ?
O1C C1C 1.312(2) . ?
O1C H1C 0.97(4) . ?
O3C C2C 1.410(3) . ?
O3C H3C 0.84(3) . ?
O3D C2D 1.413(3) . ?
O3D H2D 0.89(4) . ?
N1B C4B 1.491(3) . ?
N1B H6B 0.96(3) . ?
N1B H7B 0.91(3) . ?
N1B H8B 0.89(3) . ?
N1A C4A 1.491(3) . ?
N1A H7A 0.98(3) . ?
N1A H6A 0.91(3) . ?
N1A H8A 0.87(3) . ?
C1A C2A 1.516(3) . ?
C1B C2B 1.515(3) . ?
C1C C2C 1.530(3) . ?
C3D C8D 1.386(3) . ?
C3D C2D 1.516(3) . ?
C3D C4D 1.396(3) . ?
C2A C3A 1.534(3) . ?
C2A H2A 0.98(3) . ?
C2A H1A 0.96(3) . ?
C1D C2D 1.529(3) . ?
C3C C2C 1.518(3) . ?
C3C C4C 1.393(3) . ?
C3C C8C 1.385(3) . ?
C2C H2C 0.99(2) . ?
C3B C2B 1.535(3) . ?
C3B C5B 1.533(3) . ?
C3B C4B 1.524(3) . ?
C3B H3B 1.03(2) . ?
C4C C5C 1.387(3) . ?
C4C H4C 0.95(3) . ?
C2B H1B 0.98(3) . ?
C2B H2B 1.03(3) . ?
C5C C6C 1.384(3) . ?
C5C H5C 0.97(3) . ?
C5B C6B 1.535(3) . ?
C5B H9B 1.03(3) . ?
C5B H10B 1.04(3) . ?
C4B H4B 1.01(3) . ?
C4B H5B 1.00(3) . ?
C3A C4A 1.525(3) . ?
C3A C5A 1.527(3) . ?
C3A H3A 0.97(2) . ?
C4A H5A 0.95(3) . ?
C4A H4A 0.99(3) . ?
C8D C7D 1.395(4) . ?
C8D H8D 0.98(3) . ?
C2D H3D 1.01(2) . ?
C5A C6A 1.529(3) . ?
C5A H10A 1.00(3) . ?
C5A H9A 0.99(3) . ?
C4D C5D 1.386(3) . ?
C4D H4D 1.04(3) . ?
C8C C7C 1.392(3) . ?
C8C H8C 1.00(3) . ?
C6C C7C 1.382(4) . ?
C6C H6C 0.96(3) . ?
C6A C7A 1.525(3) . ?
C6A C8A 1.514(4) . ?
C6A H11A 1.01(4) . ?
C6B C7B 1.520(3) . ?
C6B C8B 1.520(4) . ?
C6B H11B 0.99(3) . ?
C5D C6D 1.385(4) . ?
C5D H5D 1.04(3) . ?
C6D C7D 1.384(4) . ?
C6D H6D 1.01(4) . ?
C7D H7D 1.00(3) . ?
C7C H7C 0.95(3) . ?
C7A H12A 0.95(3) . ?
C7A H13A 1.00(3) . ?
C7A H14A 1.05(4) . ?
C7B H14B 0.96(3) . ?
C7B H12B 1.03(3) . ?
C7B H13B 1.06(4) . ?
C8B H15B 0.91(3) . ?
C8B H16B 1.05(4) . ?
C8B H17B 1.04(4) . ?
C8A H17A 0.91(5) . ?
C8A H15A 0.94(5) . ?
C8A H16A 0.94(3) . ?

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
C1D O1D H1D 110(2) . . ?
C1C O1C H1C 106(2) . . ?
C2C O3C H3C 113(2) . . ?
C2D O3D H2D 110(2) . . ?
C4B N1B H6B 114.1(18) . . ?
C4B N1B H7B 111.5(17) . . ?
C4B N1B H8B 112.6(18) . . ?
H6B N1B H7B 106(2) . . ?
H6B N1B H8B 108(2) . . ?
H7B N1B H8B 105(2) . . ?
C4A N1A H7A 109.1(17) . . ?
C4A N1A H6A 111.8(18) . . ?
C4A N1A H8A 113.7(18) . . ?
H7A N1A H6A 109(3) . . ?
H7A N1A H8A 104(2) . . ?
H6A N1A H8A 109(2) . . ?
O2A C1A O1A 123.97(17) . . ?
O2A C1A C2A 120.75(17) . . ?
O1A C1A C2A 115.28(16) . . ?
O1B C1B C2B 115.32(16) . . ?
O2B C1B O1B 123.76(18) . . ?
O2B C1B C2B 120.91(17) . . ?
O2C C1C O1C 124.37(18) . . ?
O2C C1C C2C 124.08(17) . . ?
O1C C1C C2C 111.54(16) . . ?
C8D C3D C2D 121.5(2) . . ?
C8D C3D C4D 119.1(2) . . ?
C4D C3D C2D 119.4(2) . . ?
C1A C2A C3A 115.88(16) . . ?
C1A C2A H2A 108.4(15) . . ?
C1A C2A H1A 104.6(16) . . ?
C3A C2A H2A 109.3(15) . . ?
C3A C2A H1A 108.6(16) . . ?
H2A C2A H1A 110(2) . . ?
O1D C1D C2D 111.58(17) . . ?
O2D C1D O1D 124.36(18) . . ?
O2D C1D C2D 124.06(17) . . ?
C4C C3C C2C 119.36(18) . . ?
C8C C3C C2C 121.38(18) . . ?
C8C C3C C4C 119.25(19) . . ?
O3C C2C C1C 111.89(16) . . ?
O3C C2C C3C 107.49(16) . . ?
O3C C2C H2C 113.9(13) . . ?
C1C C2C H2C 106.2(13) . . ?
C3C C2C C1C 110.32(15) . . ?
C3C C2C H2C 107.0(13) . . ?
C2B C3B H3B 109.9(14) . . ?
C5B C3B C2B 111.86(17) . . ?
C5B C3B H3B 107.5(13) . . ?
C4B C3B C2B 112.06(17) . . ?
C4B C3B C5B 108.31(16) . . ?
C4B C3B H3B 107.0(14) . . ?
C3C C4C H4C 118.0(16) . . ?
C5C C4C C3C 120.5(2) . . ?
C5C C4C H4C 121.6(16) . . ?
C1B C2B C3B 115.51(16) . . ?
C1B C2B H1B 102.3(16) . . ?
C1B C2B H2B 107.6(14) . . ?
C3B C2B H1B 110.9(16) . . ?
C3B C2B H2B 110.0(14) . . ?
H1B C2B H2B 110(2) . . ?
C4C C5C H5C 121.2(17) . . ?
C6C C5C C4C 120.1(2) . . ?
C6C C5C H5C 118.7(17) . . ?
C3B C5B C6B 116.45(18) . . ?
C3B C5B H9B 109.1(15) . . ?
C3B C5B H10B 108.2(16) . . ?
C6B C5B H9B 107.8(14) . . ?
C6B C5B H10B 109.1(16) . . ?
H9B C5B H10B 106(2) . . ?
N1B C4B C3B 111.87(16) . . ?
N1B C4B H4B 109.0(14) . . ?
N1B C4B H5B 109.6(14) . . ?
C3B C4B H4B 110.4(14) . . ?
C3B C4B H5B 110.6(14) . . ?
H4B C4B H5B 105(2) . . ?
C2A C3A H3A 110.1(13) . . ?
C4A C3A C2A 111.93(16) . . ?
C4A C3A C5A 108.69(16) . . ?
C4A C3A H3A 107.2(13) . . ?
C5A C3A C2A 112.07(17) . . ?
C5A C3A H3A 106.6(13) . . ?
N1A C4A C3A 111.88(16) . . ?
N1A C4A H5A 107.0(14) . . ?
N1A C4A H4A 109.4(15) . . ?
C3A C4A H5A 109.2(15) . . ?
C3A C4A H4A 110.9(15) . . ?
H5A C4A H4A 108(2) . . ?
C3D C8D C7D 120.3(2) . . ?
C3D C8D H8D 119.9(15) . . ?
C7D C8D H8D 119.8(15) . . ?
O3D C2D C3D 107.58(16) . . ?
O3D C2D C1D 111.58(17) . . ?
O3D C2D H3D 113.2(14) . . ?
C3D C2D C1D 110.32(15) . . ?
C3D C2D H3D 108.9(14) . . ?
C1D C2D H3D 105.2(14) . . ?
C3A C5A C6A 115.23(17) . . ?
C3A C5A H10A 110.4(16) . . ?
C3A C5A H9A 109.7(14) . . ?
C6A C5A H10A 107.8(16) . . ?
C6A C5A H9A 106.2(15) . . ?
H10A C5A H9A 107(2) . . ?
C3D C4D H4D 120.2(16) . . ?
C5D C4D C3D 120.5(2) . . ?
C5D C4D H4D 119.2(16) . . ?
C3C C8C C7C 120.0(2) . . ?
C3C C8C H8C 118.5(16) . . ?
C7C C8C H8C 121.4(16) . . ?
C5C C6C H6C 120.0(17) . . ?
C7C C6C C5C 119.6(2) . . ?
C7C C6C H6C 120.4(17) . . ?
C5A C6A H11A 108.3(19) . . ?
C7A C6A C5A 109.5(2) . . ?
C7A C6A H11A 108.5(18) . . ?
C8A C6A C5A 112.7(2) . . ?
C8A C6A C7A 110.9(2) . . ?
C8A C6A H11A 106.7(19) . . ?
C5B C6B H11B 109.7(19) . . ?
C7B C6B C5B 109.5(2) . . ?
C7B C6B C8B 110.8(2) . . ?
C7B C6B H11B 105(2) . . ?
C8B C6B C5B 112.5(2) . . ?
C8B C6B H11B 108.8(19) . . ?
C4D C5D H5D 119.5(17) . . ?
C6D C5D C4D 120.1(2) . . ?
C6D C5D H5D 120.3(17) . . ?
C5D C6D H6D 121(2) . . ?
C7D C6D C5D 119.8(2) . . ?
C7D C6D H6D 119(2) . . ?
C8D C7D H7D 120.3(19) . . ?
C6D C7D C8D 120.2(2) . . ?
C6D C7D H7D 119.3(18) . . ?
C8C C7C H7C 120(2) . . ?
C6C C7C C8C 120.5(2) . . ?
C6C C7C H7C 120(2) . . ?
C6A C7A H12A 112.0(19) . . ?
C6A C7A H13A 109.7(18) . . ?
C6A C7A H14A 110.6(18) . . ?
H12A C7A H13A 110(3) . . ?
H12A C7A H14A 103(3) . . ?
H13A C7A H14A 112(3) . . ?
C6B C7B H14B 111(2) . . ?
C6B C7B H12B 111.2(18) . . ?
C6B C7B H13B 110(2) . . ?
H14B C7B H12B 107(3) . . ?
H14B C7B H13B 110(3) . . ?
H12B C7B H13B 107(3) . . ?
C6B C8B H15B 114(2) . . ?
C6B C8B H16B 112.9(19) . . ?
C6B C8B H17B 107.7(19) . . ?
H15B C8B H16B 106(3) . . ?
H15B C8B H17B 108(3) . . ?
H16B C8B H17B 108(3) . . ?
C6A C8A H17A 117(3) . . ?
C6A C8A H15A 112(2) . . ?
C6A C8A H16A 98.9(17) . . ?
H17A C8A H15A 112(4) . . ?
H17A C8A H16A 101(3) . . ?
H15A C8A H16A 115(3) . . ?

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
O1B C1B C2B C3B -173.44(17) . . . . ?
O2C C1C C2C O3C 10.8(3) . . . . ?
O2C C1C C2C C3C -108.8(2) . . . . ?
O1D C1D C2D O3D -173.37(16) . . . . ?
O1D C1D C2D C3D 67.1(2) . . . . ?
O2A C1A C2A C3A 5.5(3) . . . . ?
O2B C1B C2B C3B 5.9(3) . . . . ?
O1A C1A C2A C3A -174.10(17) . . . . ?
O2D C1D C2D O3D 6.8(3) . . . . ?
O2D C1D C2D C3D -112.7(2) . . . . ?
O1C C1C C2C O3C -169.99(16) . . . . ?
O1C C1C C2C C3C 70.4(2) . . . . ?
C1A C2A C3A C4A -90.4(2) . . . . ?
C1A C2A C3A C5A 147.17(17) . . . . ?
C3D C8D C7D C6D -0.2(4) . . . . ?
C3D C4D C5D C6D 0.1(3) . . . . ?
C2A C3A C4A N1A 56.9(2) . . . . ?
C2A C3A C5A C6A -66.3(2) . . . . ?
C3C C4C C5C C6C 0.9(3) . . . . ?
C3C C8C C7C C6C 0.8(4) . . . . ?
C2C C3C C4C C5C 177.09(19) . . . . ?
C2C C3C C8C C7C -177.9(2) . . . . ?
C3B C5B C6B C7B 179.9(2) . . . . ?
C3B C5B C6B C8B -56.4(3) . . . . ?
C4C C3C C2C O3C -47.1(2) . . . . ?
C4C C3C C2C C1C 75.2(2) . . . . ?
C4C C3C C8C C7C 0.9(3) . . . . ?
C4C C5C C6C C7C 0.8(3) . . . . ?
C2B C3B C5B C6B -66.1(2) . . . . ?
C2B C3B C4B N1B 57.0(2) . . . . ?
C5C C6C C7C C8C -1.7(4) . . . . ?
C5B C3B C2B C1B 148.29(17) . . . . ?
C5B C3B C4B N1B -179.09(16) . . . . ?
C4B C3B C2B C1B -89.9(2) . . . . ?
C4B C3B C5B C6B 169.89(18) . . . . ?
C3A C5A C6A C7A -179.9(2) . . . . ?
C3A C5A C6A C8A -55.9(3) . . . . ?
C4A C3A C5A C6A 169.47(18) . . . . ?
C8D C3D C2D O3D 128.8(2) . . . . ?
C8D C3D C2D C1D -109.3(2) . . . . ?
C8D C3D C4D C5D -0.9(3) . . . . ?
C2D C3D C8D C7D -176.7(2) . . . . ?
C2D C3D C4D C5D 176.8(2) . . . . ?
C5A C3A C4A N1A -178.82(16) . . . . ?
C4D C3D C8D C7D 0.9(3) . . . . ?
C4D C3D C2D O3D -48.8(2) . . . . ?
C4D C3D C2D C1D 73.2(2) . . . . ?
C4D C5D C6D C7D 0.6(4) . . . . ?
C8C C3C C2C O3C 131.75(19) . . . . ?
C8C C3C C2C C1C -106.0(2) . . . . ?
C8C C3C C4C C5C -1.7(3) . . . . ?
C5D C6D C7D C8D -0.5(4) . . . . ?

_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 1.367
_oxdiff_exptl_absorpt_empirical_full_min 0.742
