# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_37-cr-20241114f_auto
_database_code_depnum_ccdc_archive 'CCDC 2453024'
loop_
_audit_author_name
_audit_author_address
'Jiaxuan Ren'
;Tianjin University
China
;
_audit_update_record             
;
2025-05-21 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;
_audit_creation_date             2024-11-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Pregbalin-Vanillic Acid Cocrystal'
_chemical_formula_moiety         'C8 H8 O4, 2(C8 H17 N O2)'
_chemical_formula_sum            'C24 H42 N2 O8'
_chemical_formula_weight         486.59
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.90572(12)
_cell_length_b                   7.69426(16)
_cell_length_c                   12.1634(2)
_cell_angle_alpha                86.3588(16)
_cell_angle_beta                 88.5344(15)
_cell_angle_gamma                88.8594(16)
_cell_volume                     644.67(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    14753
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7180
_cell_measurement_theta_min      3.6090
_shelx_estimated_absorpt_T_max   0.837
_shelx_estimated_absorpt_T_min   0.774
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17929
_diffrn_reflns_point_group_measured_fraction_full 0.910
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.015
_diffrn_reflns_theta_min         3.642
_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-Arc 150'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  -7.00   0.50    0.05    --  -63.73  45.00-180.00   50
  2  ω    -32.00  -7.00   0.50    0.05    --  -63.73  45.00 -60.00   50
  3  ω    -53.00 -25.00   0.50    0.05    --  -77.78  61.00 -30.00   56
  4  ω    -32.00  -7.00   0.50    0.05    --  -63.73  45.00-150.00   50
  5  ω    -31.00  -6.00   0.50    0.05    --  -63.73  45.00 150.00   50
  6  ω    -53.00 -27.00   0.50    0.05    --  -77.78  61.00 150.00   52
  7  ω      3.00  29.00   0.50    0.05    --    2.00  71.00 -12.98   52
  8  ω     19.00  44.00   0.50    0.05    --   18.00  64.00 -65.53   50
  9  ω     19.00  44.00   0.50    0.05    --   18.00  64.00-154.68   50
 10  ω      6.00  31.00   0.50    0.05    --    6.00  69.00 -98.31   50
 11  ω     27.00  52.00   0.50    0.05    --   22.00  61.00 -43.57   50
 12  ω     24.00  49.00   0.50    0.05    --   22.00  60.00-119.66   50
 13  ω     28.00  53.00   0.50    0.05    --   26.00  60.00  36.74   50
 14  ω     28.00  53.00   0.50    0.05    --   26.00  60.00  -0.66   50
 15  ω     19.00  44.00   0.50    0.05    --   18.00  65.00  79.13   50
 16  ω     33.00  58.00   0.50    0.05    --   30.00  54.00 109.84   50
 17  ω     19.00  44.00   0.50    0.05    --   18.00  63.00 160.54   50
 18  ω     11.00  36.00   0.50    0.05    --   10.00  66.00 152.77   50
 19  ω     28.00  53.00   0.50    0.05    --   26.00  59.00  67.70   50
 20  ω     37.00  62.00   0.50    0.05    --   34.00  54.00  24.24   50
 21  ω     33.00  58.00   0.50    0.05    --   30.00  54.00 -60.27   50
 22  ω     49.00  74.00   0.50    0.05    --   46.00  54.00 -93.89   50
 23  ω     46.00  71.00   0.50    0.05    --   38.00  53.00-146.58   50
 24  ω     42.00  67.00   0.50    0.05    --   38.00  52.00-163.59   50
 25  ω     34.00  59.00   0.50    0.05    --   30.00  53.00-101.97   50
 26  ω     46.00  71.00   0.50    0.05    --   42.00  52.00-101.82   50
 27  ω     47.00  72.00   0.50    0.05    --   42.00  54.00 -55.53   50
 28  ω     46.00  71.00   0.50    0.05    --   42.00  51.00   2.34   50
 29  ω     50.00  81.00   0.50    0.05    --   46.00  51.00  76.84   62
 30  ω     34.00  68.00   0.50    0.05    --   30.00  53.00 142.21   68
 31  ω    117.00 143.00   0.50    0.05    --   93.51 111.00  90.00   52
 32  ω    107.00 134.00   0.50    0.05    --   93.51 111.00 120.00   54
 33  ω    115.00 142.00   0.50    0.05    --   93.51 111.00  60.00   54
 34  ω    109.00 135.00   0.50    0.05    --   93.51 111.00   0.00   52
 35  ω    108.00 146.00   0.50    0.05    --   93.51 111.00 -60.00   76
 36  ω    112.00 140.00   0.50    0.05    --   93.51 111.00-120.00   56
 37  ω    117.00 145.00   0.50    0.05    --   93.51 111.00-150.00   56
 38  ω    123.00 148.00   0.50    0.05    --   93.51 111.00-180.00   50
 39  ω    120.00 147.00   0.50    0.05    --   93.51 111.00 -90.00   54
 40  ω    116.00 142.00   0.50    0.05    --   93.51  95.00-170.00   52
 41  ω    119.00 144.00   0.50    0.05    --   93.51 111.00 -30.00   50
 42  ω    111.00 136.00   0.50    0.05    --   93.51 111.00  30.00   50
 43  ω    110.00 138.00   0.50    0.05    --   93.51 111.00 150.00   56
 44  ω     97.00 144.00   0.50    0.05    --   93.51  61.00 -60.00   94
 45  ω     99.00 141.00   0.50    0.05    --   93.51  61.00-120.00   84
 46  ω     95.00 147.00   0.50    0.05    --   93.51  61.00   0.00  104
 47  ω     98.00 136.00   0.50    0.05    --   93.51  61.00 -90.00   76
 48  ω     95.00 120.00   0.50    0.05    --   93.51  61.00  60.00   50
 49  ω     98.00 146.00   0.50    0.05    --   93.51  61.00  90.00   96
 50  ω     95.00 142.00   0.50    0.05    --   93.51  61.00 150.00   94
 51  ω     95.00 142.00   0.50    0.05    --   93.51  61.00 120.00   94
 52  ω     95.00 120.00   0.50    0.05    --   93.51  61.00  30.00   50
 53  ω     65.00  90.00   0.50    0.05    --   62.27  45.00 150.00   50
 54  ω     61.00  86.00   0.50    0.05    --   58.13  54.00  58.59   50
 55  ω     65.00  90.00   0.50    0.05    --   62.27  45.00 120.00   50
 56  ω     65.00  90.00   0.50    0.05    --   62.27  45.00 -60.00   50
 57  ω     57.00  82.00   0.50    0.05    --   54.00  45.00 -30.00   50
 58  ω     57.00  82.00   0.50    0.05    --   54.00  45.00   0.00   50
 59  ω     57.00  82.00   0.50    0.05    --   54.00  45.00  30.00   50
 60  ω     95.00 125.00   0.50    0.05    --   93.51  61.00 -30.00   60
 61  ω    101.00 135.00   0.50    0.05    --   93.51  45.00  90.00   68
 62  ω     65.00  90.00   0.50    0.05    --   62.27  45.00 -90.00   50
 63  ω     99.00 135.00   0.50    0.05    --   93.51  45.00-150.00   72
 64  ω    107.00 147.00   0.50    0.05    --   93.51  61.00-180.00   80
 65  ω     98.00 138.00   0.50    0.05    --   93.51  45.00-180.00   80
 66  ω     98.00 137.00   0.50    0.05    --   93.51  45.00-120.00   78
 67  ω     90.00 116.00   0.50    0.05    --   93.51  30.00 -60.00   52
 68  ω    101.00 140.00   0.50    0.05    --   93.51  45.00   0.00   78
 69  ω    117.00 143.00   0.50    0.05    --   93.51  30.00 -60.00   52
 70  ω     99.00 136.00   0.50    0.05    --   93.51  45.00  30.00   74
 71  ω     96.00 140.00   0.50    0.05    --   93.51  45.00  60.00   88
 72  ω    104.00 138.00   0.50    0.05    --   93.51  45.00 120.00   68
 73  ω     49.00  93.00   0.50    0.05    --   93.51-111.00  90.00   88
 74  ω     40.00  65.00   0.50    0.05    --   93.51-111.00 150.00   50
 75  ω     40.00  89.00   0.50    0.05    --   93.51-111.00  60.00   98
 76  ω     40.00  70.00   0.50    0.05    --   93.51-111.00  30.00   60
 77  ω     48.00  93.00   0.50    0.05    --   93.51-111.00   0.00   90
 78  ω     63.00  89.00   0.50    0.05    --   93.51 -95.00  78.00   52
 79  ω     13.00  38.00   0.50    0.05    --   54.00 -95.00  78.00   50
 80  ω     11.00  47.00   0.50    0.05    --   62.27 -95.00  78.00   72
 81  ω     40.00  65.00   0.50    0.05    --   93.51-111.00 -60.00   50
 82  ω     40.00  92.00   0.50    0.05    --   93.51-111.00 -90.00  104
 83  ω     41.00  67.00   0.50    0.05    --   93.51-111.00-120.00   52
 84  ω     45.00  89.00   0.50    0.05    --   93.51 -94.00 -90.00   88
 85  ω     49.00  89.00   0.50    0.05    --   93.51 -94.00 -60.00   80
 86  ω     45.00  91.00   0.50    0.05    --   93.51 -94.00-150.00   92
 87  ω     44.00  92.00   0.50    0.05    --   93.51 -94.00 -30.00   96
 88  ω     51.00  90.00   0.50    0.05    --   93.51 -94.00-180.00   78
 89  ω     46.00  89.00   0.50    0.05    --   93.51 -94.00   0.00   86
 90  ω     50.00  92.00   0.50    0.05    --   93.51 -94.00  90.00   84
 91  ω     45.00  91.00   0.50    0.05    --   93.51 -94.00 120.00   92
 92  ω     45.00  88.00   0.50    0.05    --   93.51 -94.00 150.00   86
 93  ω     18.00  43.00   0.50    0.05    --   62.27 -77.00 -30.00   50
 94  ω     11.00  47.00   0.50    0.05    --   62.27 -61.00-120.00   72
 95  ω    -36.00 -11.00   0.50    0.05    --  -10.00 -71.00  10.13   50
 96  ω   -131.00 -86.00   0.50    0.05    --  -77.78 -61.00  30.00   90
 97  ω   -127.00-101.00   0.50    0.05    --  -77.78 -61.00 120.00   52
 98  ω   -124.00 -86.00   0.50    0.05    --  -77.78 -61.00 -60.00   76
 99  ω   -126.00 -86.00   0.50    0.05    --  -77.78 -61.00 -90.00   80
100  ω   -131.00 -86.00   0.50    0.05    --  -77.78 -61.00-120.00   90
101  ω   -114.00 -88.00   0.50    0.05    --  -77.78 -61.00-180.00   52
102  ω   -131.00 -88.00   0.50    0.05    --  -77.78 -61.00-150.00   86
103  ω   -129.00 -91.00   0.50    0.05    --  -77.78 -61.00 -30.00   76
104  ω   -129.00 -86.00   0.50    0.05    --  -77.78 -61.00 150.00   86
105  ω   -128.00 -86.00   0.50    0.05    --  -77.78 -61.00  90.00   84
106  ω   -122.00 -86.00   0.50    0.05    --  -77.78 -61.00  60.00   72
107  ω    -87.00 -61.00   0.50    0.05    --  -54.67 -45.00  90.00   52
108  ω    -94.00 -68.00   0.50    0.05    --  -63.73 -45.00 150.00   52
109  ω    -88.00 -63.00   0.50    0.05    --  -54.67 -45.00   0.00   50
110  ω    -93.00 -67.00   0.50    0.05    --  -63.73 -45.00  30.00   52
111  ω   -105.00 -80.00   0.50    0.05    --  -77.78 -45.00 -30.00   50
112  ω   -114.00 -89.00   0.50    0.05    --  -77.78 -45.00 -90.00   50
113  ω   -112.00 -86.00   0.50    0.05    --  -77.78 -45.00-180.00   52
114  ω    -83.00 -57.00   0.50    0.05    --  -54.67 -45.00 120.00   52
115  ω    -86.00 -58.00   0.50    0.05    --  -54.67 -45.00  60.00   56
116  ω    -82.00 -57.00   0.50    0.05    --  -54.67 -45.00 -30.00   50
117  ω    -92.00 -66.00   0.50    0.05    --  -63.73 -45.00-180.00   52
118  ω    -27.00  -2.00   0.50    0.05    --  -14.00  90.00 -57.94   50
119  ω    -89.00 -48.00   0.50    0.05    --  -77.78 111.00-120.00   82
120  ω    -92.00 -39.00   0.50    0.05    --  -77.78 111.00 -30.00  106
121  ω    -57.00 -12.00   0.50    0.05    --  -63.73  95.00-170.00   90
122  ω    -83.00 -58.00   0.50    0.05    --  -77.78  95.00-170.00   50
123  ω    -62.00 -37.00   0.50    0.05    --  -54.67  95.00-170.00   50
124  ω    -92.00 -25.00   0.50    0.05    --  -77.78 111.00  60.00  134
125  ω    -97.00 -54.00   0.50    0.05    --  -82.00 115.00 143.73   86
126  ω    -33.00  -7.00   0.50    0.05    --   -6.00 110.00 126.78   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1566009000
_diffrn_orient_matrix_UB_12      0.0724887000
_diffrn_orient_matrix_UB_13      -0.0819888000
_diffrn_orient_matrix_UB_21      0.1569757000
_diffrn_orient_matrix_UB_22      -0.0481547000
_diffrn_orient_matrix_UB_23      0.0849726000
_diffrn_orient_matrix_UB_31      0.0255155000
_diffrn_orient_matrix_UB_32      -0.1808074000
_diffrn_orient_matrix_UB_33      -0.0466211000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_full    0.827
_reflns_Friedel_fraction_max     0.781
_reflns_number_gt                4695
_reflns_number_total             4757
_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 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 2069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       0.0119(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4757
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0221
_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)+(0.0364P)²+0.0750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0592
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1D,H1E), C3(H3A,H3B), C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B), C15(H15A,
 H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C23(H23)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_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
O5 O 0.60991(16) -0.24633(16) 0.81317(10) 0.0219(3) Uani 1 1 d . . . . .
H5 H 0.581(4) -0.207(3) 0.751(2) 0.036(6) Uiso 1 1 d . . . . .
O6 O 0.89506(19) -0.2523(2) 0.72184(10) 0.0352(4) Uani 1 1 d . . . . .
O7 O 0.76930(15) -0.44494(15) 1.20752(9) 0.0176(2) Uani 1 1 d . . . . .
O8 O 1.15023(15) -0.49651(16) 1.20542(9) 0.0189(3) Uani 1 1 d . . . . .
H8 H 1.064(4) -0.521(4) 1.259(2) 0.054(8) Uiso 1 1 d . . . . .
C17 C 0.8010(2) -0.2761(2) 0.80658(13) 0.0200(3) Uani 1 1 d . . . . .
C18 C 0.8870(2) -0.3387(2) 0.91259(13) 0.0172(3) Uani 1 1 d . . . . .
C19 C 1.0852(2) -0.3702(2) 0.91499(13) 0.0192(3) Uani 1 1 d . . . . .
H19 H 1.161680 -0.353877 0.849240 0.023 Uiso 1 1 calc R U . . .
C20 C 1.1727(2) -0.4255(2) 1.01319(13) 0.0184(3) Uani 1 1 d . . . . .
H20 H 1.308506 -0.447845 1.014219 0.022 Uiso 1 1 calc R U . . .
C21 C 1.0620(2) -0.4482(2) 1.10961(12) 0.0156(3) Uani 1 1 d . . . . .
C22 C 0.8605(2) -0.4179(2) 1.10729(12) 0.0151(3) Uani 1 1 d . . . . .
C23 C 0.7738(2) -0.3629(2) 1.00937(13) 0.0162(3) Uani 1 1 d . . . . .
H23 H 0.637883 -0.341592 1.007840 0.019 Uiso 1 1 calc R U . . .
C24 C 0.5625(2) -0.4456(2) 1.20914(13) 0.0196(3) Uani 1 1 d . . . . .
H24A H 0.518460 -0.535295 1.162279 0.029 Uiso 1 1 calc R U . . .
H24B H 0.512874 -0.331371 1.181413 0.029 Uiso 1 1 calc R U . . .
H24C H 0.514220 -0.470725 1.284833 0.029 Uiso 1 1 calc R U . . .
O1 O -0.29641(15) 0.45991(14) 0.47672(9) 0.0178(2) Uani 1 1 d . . . . .
O2 O -0.00553(14) 0.38787(14) 0.40778(8) 0.0156(2) Uani 1 1 d . . . . .
N1 N -0.17978(19) -0.20600(18) 0.49649(11) 0.0154(3) Uani 1 1 d . . . . .
H1A H -0.200(3) -0.331(4) 0.499(2) 0.036(6) Uiso 1 1 d . . . . .
H1B H -0.274(3) -0.155(3) 0.5376(19) 0.025(5) Uiso 1 1 d . . . . .
H1C H -0.063(3) -0.181(3) 0.5227(17) 0.024(5) Uiso 1 1 d . . . . .
C1 C -0.1920(2) -0.1383(2) 0.37942(12) 0.0169(3) Uani 1 1 d . . . . .
H1D H -0.328275 -0.142047 0.356493 0.020 Uiso 1 1 calc R U . . .
H1E H -0.113904 -0.215272 0.332601 0.020 Uiso 1 1 calc R U . . .
C2 C -0.1203(2) 0.0477(2) 0.36022(12) 0.0149(3) Uani 1 1 d . . . . .
H2 H 0.008100 0.054607 0.395706 0.018 Uiso 1 1 calc R U . . .
C3 C -0.0914(2) 0.0895(2) 0.23585(13) 0.0168(3) Uani 1 1 d . . . . .
H3A H -0.209524 0.056087 0.198524 0.020 Uiso 1 1 calc R U . . .
H3B H -0.078015 0.217003 0.222625 0.020 Uiso 1 1 calc R U . . .
C4 C 0.0840(2) -0.0003(2) 0.18221(13) 0.0201(3) Uani 1 1 d . . . . .
H4 H 0.069991 -0.129035 0.196083 0.024 Uiso 1 1 calc R U . . .
C5 C 0.0839(3) 0.0417(2) 0.05752(14) 0.0252(4) Uani 1 1 d . . . . .
H5A H -0.037125 0.002377 0.027784 0.038 Uiso 1 1 calc R U . . .
H5B H 0.193947 -0.018146 0.022933 0.038 Uiso 1 1 calc R U . . .
H5C H 0.094901 0.167683 0.041999 0.038 Uiso 1 1 calc R U . . .
C6 C 0.2760(2) 0.0508(3) 0.23038(14) 0.0257(4) Uani 1 1 d . . . . .
H6A H 0.286962 0.177833 0.224141 0.039 Uiso 1 1 calc R U . . .
H6B H 0.383900 -0.002002 0.189665 0.039 Uiso 1 1 calc R U . . .
H6C H 0.279873 0.009235 0.308153 0.039 Uiso 1 1 calc R U . . .
C7 C -0.2602(2) 0.1772(2) 0.41252(12) 0.0167(3) Uani 1 1 d . . . . .
H7A H -0.373261 0.195365 0.364387 0.020 Uiso 1 1 calc R U . . .
H7B H -0.308094 0.123507 0.483945 0.020 Uiso 1 1 calc R U . . .
C8 C -0.1795(2) 0.3547(2) 0.43270(12) 0.0143(3) Uani 1 1 d . . . . .
O3 O 0.21878(15) -0.16021(15) 0.53292(9) 0.0186(2) Uani 1 1 d . . . . .
O4 O 0.48648(15) -0.10666(15) 0.62201(9) 0.0172(2) Uani 1 1 d . . . . .
N2 N 0.30876(19) 0.49326(19) 0.53236(11) 0.0158(3) Uani 1 1 d . . . . .
H2A H 0.214(3) 0.447(3) 0.4907(18) 0.022(5) Uiso 1 1 d . . . . .
H2B H 0.287(3) 0.610(3) 0.5295(19) 0.031(6) Uiso 1 1 d . . . . .
H2C H 0.425(3) 0.473(3) 0.5033(18) 0.026(5) Uiso 1 1 d . . . . .
C9 C 0.2930(2) 0.4251(2) 0.65042(12) 0.0166(3) Uani 1 1 d . . . . .
H9A H 0.156053 0.432927 0.675952 0.020 Uiso 1 1 calc R U . . .
H9B H 0.369767 0.499080 0.696082 0.020 Uiso 1 1 calc R U . . .
C10 C 0.3649(2) 0.2366(2) 0.66684(12) 0.0143(3) Uani 1 1 d . . . . .
H10 H 0.494624 0.227305 0.629006 0.017 Uiso 1 1 calc R U . . .
C11 C 0.3911(2) 0.1894(2) 0.79039(13) 0.0167(3) Uani 1 1 d . . . . .
H11A H 0.408115 0.061390 0.801039 0.020 Uiso 1 1 calc R U . . .
H11B H 0.270331 0.221754 0.830314 0.020 Uiso 1 1 calc R U . . .
C12 C 0.5621(2) 0.2752(2) 0.84368(13) 0.0181(3) Uani 1 1 d . . . . .
H12 H 0.535145 0.403493 0.842783 0.022 Uiso 1 1 calc R U . . .
C13 C 0.7549(2) 0.2458(3) 0.78215(14) 0.0254(4) Uani 1 1 d . . . . .
H13A H 0.775107 0.120981 0.773195 0.038 Uiso 1 1 calc R U . . .
H13B H 0.860813 0.289020 0.824376 0.038 Uiso 1 1 calc R U . . .
H13C H 0.752139 0.308430 0.709486 0.038 Uiso 1 1 calc R U . . .
C14 C 0.5761(3) 0.2048(2) 0.96393(14) 0.0235(4) Uani 1 1 d . . . . .
H14A H 0.455841 0.232737 1.004111 0.035 Uiso 1 1 calc R U . . .
H14B H 0.685350 0.258388 0.997931 0.035 Uiso 1 1 calc R U . . .
H14C H 0.596100 0.078138 0.966658 0.035 Uiso 1 1 calc R U . . .
C15 C 0.2288(2) 0.1103(2) 0.61561(12) 0.0168(3) Uani 1 1 d . . . . .
H15A H 0.116859 0.089187 0.666876 0.020 Uiso 1 1 calc R U . . .
H15B H 0.178373 0.167634 0.546707 0.020 Uiso 1 1 calc R U . . .
C16 C 0.3186(2) -0.0651(2) 0.58924(12) 0.0143(3) Uani 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
O5 H5 0.82(3) . ?
O5 C17 1.336(2) . ?
O6 C17 1.210(2) . ?
O7 C22 1.3638(18) . ?
O7 C24 1.4279(17) . ?
O8 H8 0.88(3) . ?
O8 C21 1.3565(18) . ?
C17 C18 1.482(2) . ?
C18 C19 1.386(2) . ?
C18 C23 1.401(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.387(2) . ?
C21 C22 1.407(2) . ?
C22 C23 1.385(2) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O1 C8 1.265(2) . ?
O2 C8 1.2583(18) . ?
N1 H1A 0.97(3) . ?
N1 H1B 0.91(2) . ?
N1 H1C 0.90(2) . ?
N1 C1 1.4887(18) . ?
C1 H1D 0.9900 . ?
C1 H1E 0.9900 . ?
C1 C2 1.526(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.535(2) . ?
C2 C7 1.530(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.534(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.531(2) . ?
C4 C6 1.531(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.522(2) . ?
O3 C16 1.260(2) . ?
O4 C16 1.2642(18) . ?
N2 H2A 0.93(2) . ?
N2 H2B 0.91(3) . ?
N2 H2C 0.88(2) . ?
N2 C9 1.4991(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.526(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.5379(19) . ?
C10 C15 1.536(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.541(2) . ?
C12 H12 1.0000 . ?
C12 C13 1.531(2) . ?
C12 C14 1.532(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.523(2) . ?

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
C17 O5 H5 104.7(17) . . ?
C22 O7 C24 117.03(11) . . ?
C21 O8 H8 111.0(19) . . ?
O5 C17 C18 113.88(14) . . ?
O6 C17 O5 122.90(15) . . ?
O6 C17 C18 123.22(15) . . ?
C19 C18 C17 118.38(14) . . ?
C19 C18 C23 119.97(14) . . ?
C23 C18 C17 121.64(14) . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.34(14) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.06(14) . . ?
C21 C20 H20 120.0 . . ?
O8 C21 C20 119.39(13) . . ?
O8 C21 C22 120.85(13) . . ?
C20 C21 C22 119.75(13) . . ?
O7 C22 C21 113.71(13) . . ?
O7 C22 C23 126.25(13) . . ?
C23 C22 C21 120.03(14) . . ?
C18 C23 H23 120.1 . . ?
C22 C23 C18 119.84(14) . . ?
C22 C23 H23 120.1 . . ?
O7 C24 H24A 109.5 . . ?
O7 C24 H24B 109.5 . . ?
O7 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H1A N1 H1B 109(2) . . ?
H1A N1 H1C 112(2) . . ?
H1B N1 H1C 109.0(19) . . ?
C1 N1 H1A 107.9(14) . . ?
C1 N1 H1B 109.7(14) . . ?
C1 N1 H1C 109.6(13) . . ?
N1 C1 H1D 109.0 . . ?
N1 C1 H1E 109.0 . . ?
N1 C1 C2 112.92(13) . . ?
H1D C1 H1E 107.8 . . ?
C2 C1 H1D 109.0 . . ?
C2 C1 H1E 109.0 . . ?
C1 C2 H2 108.3 . . ?
C1 C2 C3 108.89(13) . . ?
C1 C2 C7 111.06(12) . . ?
C3 C2 H2 108.3 . . ?
C7 C2 H2 108.3 . . ?
C7 C2 C3 111.99(13) . . ?
C2 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C4 C3 C2 115.53(13) . . ?
C4 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
C3 C4 H4 108.0 . . ?
C5 C4 C3 109.39(14) . . ?
C5 C4 H4 108.0 . . ?
C5 C4 C6 110.76(14) . . ?
C6 C4 C3 112.43(14) . . ?
C6 C4 H4 108.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 108.2 . . ?
C2 C7 H7B 108.2 . . ?
H7A C7 H7B 107.3 . . ?
C8 C7 C2 116.43(12) . . ?
C8 C7 H7A 108.2 . . ?
C8 C7 H7B 108.2 . . ?
O1 C8 C7 115.69(13) . . ?
O2 C8 O1 124.21(14) . . ?
O2 C8 C7 120.08(14) . . ?
H2A N2 H2B 106.8(19) . . ?
H2A N2 H2C 110.4(19) . . ?
H2B N2 H2C 108(2) . . ?
C9 N2 H2A 111.1(13) . . ?
C9 N2 H2B 108.4(15) . . ?
C9 N2 H2C 111.9(14) . . ?
N2 C9 H9A 109.1 . . ?
N2 C9 H9B 109.1 . . ?
N2 C9 C10 112.35(13) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C9 C10 H10 108.0 . . ?
C9 C10 C11 109.56(12) . . ?
C9 C10 C15 111.75(12) . . ?
C11 C10 H10 108.0 . . ?
C15 C10 H10 108.0 . . ?
C15 C10 C11 111.53(12) . . ?
C10 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
C10 C11 C12 115.97(12) . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C11 C12 H12 108.3 . . ?
C13 C12 C11 112.63(14) . . ?
C13 C12 H12 108.3 . . ?
C13 C12 C14 110.07(13) . . ?
C14 C12 C11 109.23(13) . . ?
C14 C12 H12 108.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 108.4 . . ?
C10 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
C16 C15 C10 115.66(12) . . ?
C16 C15 H15A 108.4 . . ?
C16 C15 H15B 108.4 . . ?
O3 C16 O4 123.66(15) . . ?
O3 C16 C15 116.55(13) . . ?
O4 C16 C15 119.78(14) . . ?

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
O5 C17 C18 C19 -178.77(16) . . . . ?
O5 C17 C18 C23 0.0(2) . . . . ?
O6 C17 C18 C19 0.6(3) . . . . ?
O6 C17 C18 C23 179.29(18) . . . . ?
O7 C22 C23 C18 179.24(15) . . . . ?
O8 C21 C22 O7 -1.2(2) . . . . ?
O8 C21 C22 C23 177.79(15) . . . . ?
C17 C18 C19 C20 178.65(16) . . . . ?
C17 C18 C23 C22 -178.57(16) . . . . ?
C18 C19 C20 C21 -0.5(2) . . . . ?
C19 C18 C23 C22 0.1(2) . . . . ?
C19 C20 C21 O8 -177.77(15) . . . . ?
C19 C20 C21 C22 1.1(2) . . . . ?
C20 C21 C22 O7 180.00(14) . . . . ?
C20 C21 C22 C23 -1.1(2) . . . . ?
C21 C22 C23 C18 0.4(2) . . . . ?
C23 C18 C19 C20 -0.1(3) . . . . ?
C24 O7 C22 C21 -169.75(13) . . . . ?
C24 O7 C22 C23 11.4(2) . . . . ?
N1 C1 C2 C3 166.27(13) . . . . ?
N1 C1 C2 C7 -69.96(16) . . . . ?
C1 C2 C3 C4 -72.50(16) . . . . ?
C1 C2 C7 C8 160.86(12) . . . . ?
C2 C3 C4 C5 175.33(13) . . . . ?
C2 C3 C4 C6 -61.17(18) . . . . ?
C2 C7 C8 O1 -179.49(13) . . . . ?
C2 C7 C8 O2 -0.77(19) . . . . ?
C3 C2 C7 C8 -77.17(16) . . . . ?
C7 C2 C3 C4 164.29(13) . . . . ?
N2 C9 C10 C11 166.49(11) . . . . ?
N2 C9 C10 C15 -69.38(16) . . . . ?
C9 C10 C11 C12 -70.89(17) . . . . ?
C9 C10 C15 C16 158.29(12) . . . . ?
C10 C11 C12 C13 -53.39(19) . . . . ?
C10 C11 C12 C14 -176.02(13) . . . . ?
C10 C15 C16 O3 -170.00(12) . . . . ?
C10 C15 C16 O4 8.73(19) . . . . ?
C11 C10 C15 C16 -78.70(16) . . . . ?
C15 C10 C11 C12 164.86(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 1.261
_oxdiff_exptl_absorpt_empirical_full_min 0.751
####################################################################### 
# 
# 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_37-cr-20241112b_auto
_database_code_depnum_ccdc_archive 'CCDC 2453025'
loop_
_audit_author_name
_audit_author_address
'Jiaxuan Ren'
;Tianjin University
China
;
_audit_update_record             
;
2025-05-21 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;
_audit_creation_date             2024-11-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Pregbalin-Cinnamic Acid Cocrystal'
_chemical_formula_moiety         'C8 H17 N O2, C9 H8 O2'
_chemical_formula_sum            'C17 H25 N O4'
_chemical_formula_weight         307.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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                   6.37480(10)
_cell_length_b                   7.71520(10)
_cell_length_c                   34.3678(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1690.31(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13464
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8920
_cell_measurement_theta_min      5.1340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            15609
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.110
_diffrn_reflns_theta_min         5.148
_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-Arc 150'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_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   3.00   0.50    0.05    --  -54.63  45.00-150.00   58
  2  ω    -51.00 -26.00   0.50    0.05    --  -77.77  61.00-150.00   50
  3  ω    -54.00 -25.00   0.50    0.05    --  -77.77  61.00 -90.00   58
  4  ω    -32.00  -7.00   0.50    0.05    --  -63.67  45.00  30.00   50
  5  ω    -32.00  -7.00   0.50    0.05    --  -63.67  45.00 120.00   50
  6  ω    -32.00  -7.00   0.50    0.05    --  -63.67  45.00 150.00   50
  7  ω    -89.00 -34.00   0.50    0.05    --  -77.77 111.00 -30.00  110
  8  ω    -49.00 -18.00   0.50    0.05    --  -63.67  94.00 -68.00   62
  9  ω    -87.00 -53.00   0.50    0.05    --  -77.77  94.00 -68.00   68
 10  ω    -82.00 -57.00   0.50    0.05    --  -77.77 104.00-169.00   50
 11  ω    -47.00 -12.00   0.50    0.05    --  -63.67 104.00-169.00   70
 12  ω    -65.00 -40.00   0.50    0.05    --  -54.63 104.00-169.00   50
 13  ω   -108.00 -83.00   0.50    0.05    --  -54.63 -36.00 -61.00   50
 14  ω   -103.00 -78.00   0.50    0.05    --  -63.67 -36.00 -61.00   50
 15  ω   -131.00-106.00   0.50    0.05    --  -77.77 -36.00 -61.00   50
 16  ω     40.00  65.00   0.50    0.05    --   93.50-111.00-120.00   50
 17  ω     41.00  67.00   0.50    0.05    --   93.50-111.00-150.00   52
 18  ω     41.00  93.00   0.50    0.05    --   93.50-111.00   0.00  104
 19  ω      8.00  33.00   0.50    0.05    --   62.22-104.00  88.00   50
 20  ω     36.00  62.00   0.50    0.05    --   62.22-104.00  88.00   52
 21  ω     54.00  92.00   0.50    0.05    --   93.50-111.00 120.00   76
 22  ω     40.00  65.00   0.50    0.05    --   93.50-104.00  88.00   50
 23  ω     47.00  84.00   0.50    0.05    --   93.50 -94.00   0.00   74
 24  ω     58.00  83.00   0.50    0.05    --   93.50 -94.00  60.00   50
 25  ω     43.00  69.00   0.50    0.05    --   93.50 -94.00 -90.00   52
 26  ω     43.00  86.00   0.50    0.05    --   93.50 -94.00-120.00   86
 27  ω     43.00  68.00   0.50    0.05    --   93.50 -94.00-150.00   50
 28  ω     43.00  68.00   0.50    0.05    --   93.50 -94.00-179.00   50
 29  ω     10.00  35.00   0.50    0.05    --   53.96 -94.00-179.00   50
 30  ω    112.00 144.00   0.50    0.05    --   93.50  61.00 -60.00   64
 31  ω     95.00 143.00   0.50    0.05    --   93.50  61.00-120.00   96
 32  ω     97.00 136.00   0.50    0.05    --   93.50  45.00-180.00   78
 33  ω     96.00 145.00   0.50    0.05    --   93.50  36.00  94.00   98
 34  ω    100.00 149.00   0.50    0.05    --   93.50  45.00 150.00   98
 35  ω     68.00  93.00   0.50    0.05    --   62.22  36.00  94.00   50
 36  ω     73.00  98.00   0.50    0.05    --   53.96  36.00  94.00   50
 37  ω    111.00 137.00   0.50    0.05    --   93.50 111.00 150.00   52
 38  ω     97.00 147.00   0.50    0.05    --   93.50 111.00  60.00  100
 39  ω    118.00 143.00   0.50    0.05    --   93.50 111.00 -30.00   50
 40  ω    104.00 130.00   0.50    0.05    --   93.50 111.00 -90.00   52
 41  ω    119.00 144.00   0.50    0.05    --   93.50 111.00-120.00   50
 42  ω    123.00 148.00   0.50    0.05    --   93.50 104.00-169.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1070867000
_diffrn_orient_matrix_UB_12      -0.1042705000
_diffrn_orient_matrix_UB_13      0.0326632000
_diffrn_orient_matrix_UB_21      -0.0307640000
_diffrn_orient_matrix_UB_22      -0.1533125000
_diffrn_orient_matrix_UB_23      -0.0281428000
_diffrn_orient_matrix_UB_31      0.2144230000
_diffrn_orient_matrix_UB_32      -0.0741057000
_diffrn_orient_matrix_UB_33      0.0122845000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3442
_reflns_number_total             3484
_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 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 1401 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_coef       0.0078(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0235
_refine_ls_restrained_S_all      1.042
_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)+(0.0349P)²+0.2740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0625
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8)
2.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_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
O3 O 0.62422(14) 0.47678(11) 0.54069(2) 0.0181(2) Uani 1 1 d . . . . .
O4 O 0.88606(14) 0.55023(11) 0.50127(3) 0.0181(2) Uani 1 1 d . . . . .
N1 N 0.81102(17) -0.10111(13) 0.51083(3) 0.0162(2) Uani 1 1 d . . . . .
H1A H 0.900779 -0.051517 0.493507 0.024 Uiso 1 1 calc R U . . .
H1B H 0.676949 -0.070859 0.504777 0.024 Uiso 1 1 calc R U . . .
H1C H 0.824304 -0.218446 0.509758 0.024 Uiso 1 1 calc R U . . .
C10 C 0.79842(19) 0.44721(15) 0.52452(3) 0.0147(2) Uani 1 1 d . . . . .
C11 C 0.9065(2) 0.27402(15) 0.53123(4) 0.0166(2) Uani 1 1 d . . . . .
H11A H 1.045960 0.296258 0.542863 0.020 Uiso 1 1 calc R U . . .
H11B H 0.929585 0.218081 0.505665 0.020 Uiso 1 1 calc R U . . .
C12 C 0.7881(2) 0.14656(15) 0.55747(3) 0.0154(2) Uani 1 1 d . . . . .
H12 H 0.635636 0.152937 0.550761 0.018 Uiso 1 1 calc R U . . .
C13 C 0.8619(2) -0.03963(16) 0.55088(3) 0.0179(3) Uani 1 1 d . . . . .
H13A H 1.015362 -0.046099 0.554988 0.021 Uiso 1 1 calc R U . . .
H13B H 0.793695 -0.116708 0.570129 0.021 Uiso 1 1 calc R U . . .
C14 C 0.8132(2) 0.19665(16) 0.60040(4) 0.0195(3) Uani 1 1 d . . . . .
H14A H 0.791760 0.323318 0.602716 0.023 Uiso 1 1 calc R U . . .
H14B H 0.959621 0.171985 0.608237 0.023 Uiso 1 1 calc R U . . .
C15 C 0.6661(2) 0.10626(17) 0.62938(4) 0.0242(3) Uani 1 1 d . . . . .
H15 H 0.691194 -0.021476 0.627714 0.029 Uiso 1 1 calc R U . . .
C16 C 0.7195(3) 0.1655(2) 0.67054(4) 0.0363(4) Uani 1 1 d . . . . .
H16A H 0.868921 0.145541 0.675566 0.054 Uiso 1 1 calc R U . . .
H16B H 0.635566 0.099709 0.689310 0.054 Uiso 1 1 calc R U . . .
H16C H 0.688454 0.289342 0.673192 0.054 Uiso 1 1 calc R U . . .
C17 C 0.4358(3) 0.1404(2) 0.62038(5) 0.0367(4) Uani 1 1 d . . . . .
H17A H 0.410939 0.265697 0.619393 0.055 Uiso 1 1 calc R U . . .
H17B H 0.348254 0.088845 0.640768 0.055 Uiso 1 1 calc R U . . .
H17C H 0.399953 0.088692 0.595201 0.055 Uiso 1 1 calc R U . . .
O1 O 0.17499(16) 0.60184(14) 0.57529(3) 0.0272(2) Uani 1 1 d . . . . .
O2 O 0.49268(15) 0.64243(16) 0.60183(3) 0.0302(3) Uani 1 1 d . . . . .
H2 H 0.533687 0.594907 0.581201 0.045 Uiso 1 1 calc R U . . .
C1 C -0.2914(2) 0.68139(17) 0.69684(4) 0.0221(3) Uani 1 1 d . . . . .
H1 H -0.369820 0.620511 0.677714 0.027 Uiso 1 1 calc R U . . .
C2 C -0.3801(2) 0.71309(19) 0.73305(4) 0.0263(3) Uani 1 1 d . . . . .
H2A H -0.517604 0.672801 0.738708 0.032 Uiso 1 1 calc R U . . .
C3 C -0.2672(3) 0.80394(19) 0.76099(4) 0.0281(3) Uani 1 1 d . . . . .
H3 H -0.326926 0.825516 0.785844 0.034 Uiso 1 1 calc R U . . .
C4 C -0.0671(2) 0.86293(19) 0.75246(4) 0.0268(3) Uani 1 1 d . . . . .
H4 H 0.009710 0.925812 0.771484 0.032 Uiso 1 1 calc R U . . .
C5 C 0.0221(2) 0.83083(18) 0.71631(4) 0.0227(3) Uani 1 1 d . . . . .
H5 H 0.159054 0.872404 0.710714 0.027 Uiso 1 1 calc R U . . .
C6 C -0.0886(2) 0.73770(16) 0.68812(4) 0.0196(3) Uani 1 1 d . . . . .
C7 C 0.0027(2) 0.69266(17) 0.65014(4) 0.0204(3) Uani 1 1 d . . . . .
H7 H -0.090106 0.649186 0.630846 0.024 Uiso 1 1 calc R U . . .
C8 C 0.2038(2) 0.70750(18) 0.64048(4) 0.0233(3) Uani 1 1 d . . . . .
H8 H 0.298739 0.758624 0.658430 0.028 Uiso 1 1 calc R U . . .
C9 C 0.2835(2) 0.64631(17) 0.60241(4) 0.0215(3) Uani 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
O3 C10 1.2627(15) . ?
O4 C10 1.2580(15) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C13 1.4916(15) . ?
C10 C11 1.5208(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5330(16) . ?
C12 H12 1.0000 . ?
C12 C13 1.5284(16) . ?
C12 C14 1.5333(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5354(18) . ?
C15 H15 1.0000 . ?
C15 C16 1.5251(19) . ?
C15 C17 1.524(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O1 C9 1.2101(16) . ?
O2 H2 0.8400 . ?
O2 C9 1.3341(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.3888(19) . ?
C1 C6 1.396(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.390(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3882(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.3973(19) . ?
C6 C7 1.4706(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.329(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.4807(18) . ?

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
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C13 N1 H1A 109.5 . . ?
C13 N1 H1B 109.5 . . ?
C13 N1 H1C 109.5 . . ?
O3 C10 C11 119.36(11) . . ?
O4 C10 O3 123.79(11) . . ?
O4 C10 C11 116.77(10) . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
C10 C11 C12 115.46(10) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C11 C12 H12 108.1 . . ?
C11 C12 C14 110.67(10) . . ?
C13 C12 C11 111.36(10) . . ?
C13 C12 H12 108.1 . . ?
C13 C12 C14 110.33(10) . . ?
C14 C12 H12 108.1 . . ?
N1 C13 C12 111.65(9) . . ?
N1 C13 H13A 109.3 . . ?
N1 C13 H13B 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C12 C14 H14A 108.2 . . ?
C12 C14 H14B 108.2 . . ?
C12 C14 C15 116.48(11) . . ?
H14A C14 H14B 107.3 . . ?
C15 C14 H14A 108.2 . . ?
C15 C14 H14B 108.2 . . ?
C14 C15 H15 108.2 . . ?
C16 C15 C14 109.22(12) . . ?
C16 C15 H15 108.2 . . ?
C17 C15 C14 112.22(11) . . ?
C17 C15 H15 108.2 . . ?
C17 C15 C16 110.58(13) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 O2 H2 109.5 . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C6 120.97(13) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2A 120.1 . . ?
C1 C2 C3 119.79(14) . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.76(13) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.50(14) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.37(13) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.59(12) . . ?
C1 C6 C7 118.90(12) . . ?
C5 C6 C7 122.49(13) . . ?
C6 C7 H7 117.2 . . ?
C8 C7 C6 125.67(12) . . ?
C8 C7 H7 117.2 . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.61(12) . . ?
C9 C8 H8 119.2 . . ?
O1 C9 O2 123.61(13) . . ?
O1 C9 C8 125.09(13) . . ?
O2 C9 C8 111.29(11) . . ?

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
O3 C10 C11 C12 0.80(16) . . . . ?
O4 C10 C11 C12 -175.92(10) . . . . ?
C10 C11 C12 C13 159.19(10) . . . . ?
C10 C11 C12 C14 -77.70(13) . . . . ?
C11 C12 C13 N1 -64.96(13) . . . . ?
C11 C12 C14 C15 167.07(10) . . . . ?
C12 C14 C15 C16 177.53(11) . . . . ?
C12 C14 C15 C17 -59.47(16) . . . . ?
C13 C12 C14 C15 -69.23(14) . . . . ?
C14 C12 C13 N1 171.74(10) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C1 C6 C7 C8 -166.48(13) . . . . ?
C2 C1 C6 C5 -1.60(19) . . . . ?
C2 C1 C6 C7 176.67(12) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C1 1.37(19) . . . . ?
C4 C5 C6 C7 -176.83(13) . . . . ?
C5 C6 C7 C8 11.7(2) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C6 C7 C8 C9 175.33(12) . . . . ?
C7 C8 C9 O1 10.9(2) . . . . ?
C7 C8 C9 O2 -167.78(13) . . . . ?

_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 1.266
_oxdiff_exptl_absorpt_empirical_full_min 0.606
####################################################################### 
# 
# 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_37-cr-20241122d_auto
_database_code_depnum_ccdc_archive 'CCDC 2453043'
loop_
_audit_author_name
_audit_author_address
'Jiaxuan Ren'
;Tianjin University
China
;
_audit_update_record             
;
2025-05-21 deposited with the CCDC.	2026-03-13 downloaded from the CCDC.
;
_audit_creation_date             2024-11-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Pregbalin-p-Methylbenzoic Acid Cocrystal'
_chemical_formula_moiety         'C8 H17 N O2, C8 H8 O2'
_chemical_formula_sum            'C16 H25 N O4'
_chemical_formula_weight         295.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.54204(4)
_cell_length_b                   7.72068(6)
_cell_length_c                   31.8964(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1611.055(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    28975
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1940
_cell_measurement_theta_min      4.1480
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0052
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            34170
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.359
_diffrn_reflns_theta_min         5.548
_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-Arc 150'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     53.00  82.00   0.50    0.05    --   79.02  15.00 -30.00   58
  2  ω     88.00 127.00   0.50    0.05    --   79.02  15.00 -30.00   78
  3  ω     85.00 110.00   0.50    0.05    --   66.00  60.00 -22.38   50
  4  ω     98.00 125.00   0.50    0.05    --   79.02  15.00-180.00   54
  5  ω     80.00 127.00   0.50    0.05    --   79.02  15.00  30.00   94
  6  ω     89.00 127.00   0.50    0.05    --   79.02  15.00  90.00   76
  7  ω     79.00 104.00   0.50    0.05    --   62.00  55.00 133.20   50
  8  ω     59.00  86.00   0.50    0.05    --   42.00  54.00 125.90   54
  9  ω     54.00  79.00   0.50    0.05    --   38.00  52.00   5.85   50
 10  ω     58.00  83.00   0.50    0.05    --   42.00  53.00 -98.67   50
 11  ω     57.00  83.00   0.50    0.05    --   38.00  52.00 171.08   52
 12  ω     18.00  64.00   0.50    0.05    --   59.33-108.00  61.00   92
 13  ω     34.00  59.00   0.50    0.05    --   72.67-108.00  61.00   50
 14  ω     52.00 101.00   0.50    0.05    --   79.02-125.00  60.00   98
 15  ω     64.00  93.00   0.50    0.05    --   79.02-108.00  61.00   58
 16  ω     75.00 101.00   0.50    0.05    --   79.02-125.00-120.00   52
 17  ω     69.00 101.00   0.50    0.05    --   79.02-125.00-180.00   64
 18  ω     28.00  95.00   0.50    0.05    --   72.67-125.00 -30.00  134
 19  ω   -119.00 -94.00   0.50    0.05    --  -78.00 -65.00 120.58   50
 20  ω   -127.00-102.00   0.50    0.05    --  -82.00 -56.00 163.37   50
 21  ω   -122.00 -97.00   0.50    0.05    --  -82.00 -61.00 141.89   50
 22  ω   -125.00-100.00   0.50    0.05    --  -82.00 -64.00  63.88   50
 23  ω   -125.00-100.00   0.50    0.05    --  -82.00 -60.00  41.12   50
 24  ω   -127.00 -98.00   0.50    0.05    --  -82.00 -50.00  21.81   58
 25  ω   -125.00 -97.00   0.50    0.05    --  -82.00 -55.00 -84.72   56
 26  ω   -129.00-104.00   0.50    0.05    --  -82.00 -50.00-172.93   50
 27  ω   -128.00-103.00   0.50    0.05    --  -82.00 -51.00-130.28   50
 28  ω   -124.00 -99.00   0.50    0.05    --  -82.00 -49.00 -69.07   50
 29  ω   -130.00-100.00   0.50    0.05    --  -82.00 -43.00 -56.53   60
 30  ω   -122.00 -96.00   0.50    0.05    --  -82.00 -40.00-126.31   52
 31  ω   -127.00-101.00   0.50    0.05    --  -82.00 -47.00 -33.60   52
 32  ω   -130.00-105.00   0.50    0.05    --  -82.00 -44.00  60.78   50
 33  ω   -128.00-102.00   0.50    0.05    --  -82.00 -47.00  83.32   52
 34  ω   -116.00 -91.00   0.50    0.05    --  -67.25 -38.00  61.91   50
 35  ω   -129.00-104.00   0.50    0.05    --  -82.00 -32.00  82.89   50
 36  ω   -132.00 -95.00   0.50    0.05    --  -82.00 -32.00  75.65   74
 37  ω   -109.00 -58.00   0.50    0.05    --  -78.06 -15.00  90.00  102
 38  ω    -68.00 -42.00   0.50    0.05    --  -60.24 -15.00  90.00   52
 39  ω   -119.00 -54.00   0.50    0.05    --  -74.26 -15.00-150.00  130
 40  ω   -126.00 -98.00   0.50    0.05    --  -78.06 -15.00-180.00   56
 41  ω   -115.00 -85.00   0.50    0.05    --  -78.06 -15.00 -30.00   60
 42  ω    -80.00 -55.00   0.50    0.05    --  -82.00  93.00 155.77   50
 43  ω   -101.00 -75.00   0.50    0.05    --  -82.00 131.00 161.53   52
 44  ω    -63.00 -37.00   0.50    0.05    --  -82.00 131.00 161.53   52
 45  ω    -73.00 -36.00   0.50    0.05    --  -82.00 126.00 100.70   74
 46  ω    -62.00 -37.00   0.50    0.05    --  -82.00 131.00 -55.73   50
 47  ω   -100.00 -60.00   0.50    0.05    --  -82.00 129.00-102.09   80
 48  ω    -99.00 -67.00   0.50    0.05    --  -82.00 126.00-122.14   64
 49  ω    -72.00 -44.00   0.50    0.05    --  -78.06 125.00 -90.00   56
 50  ω    -99.00 -73.00   0.50    0.05    --  -82.00 131.00 -55.73   52
 51  ω   -100.00 -74.00   0.50    0.05    --  -78.06 125.00 -90.00   52
 52  ω    -94.00 -44.00   0.50    0.05    --  -82.00 125.00-146.08  100
 53  ω    -70.00 -33.00   0.50    0.05    --  -78.06 125.00-150.00   74
 54  ω    -85.00 -59.00   0.50    0.05    --  -78.06 125.00   0.00   52
 55  ω    -68.00 -39.00   0.50    0.05    --  -82.00 125.00  14.72   58
 56  ω    -94.00 -67.00   0.50    0.05    --  -82.00 126.00  64.20   54
 57  ω   -101.00 -33.00   0.50    0.05    --  -78.06 125.00  60.00  136
 58  ω    -68.00 -34.00   0.50    0.05    --  -78.06 125.00 120.00   68
 59  ω    -71.00 -37.00   0.50    0.05    --  -82.00 125.00  81.81   68
 60  ω    -67.00 -37.00   0.50    0.05    --  -82.00 124.00  30.44   60
 61  ω    -98.00 -73.00   0.50    0.05    --  -82.00 124.00  30.44   50
 62  ω    -99.00 -71.00   0.50    0.05    --  -82.00 125.00 -33.40   56
 63  ω    -64.00 -39.00   0.50    0.05    --  -82.00 125.00 -59.47   50
 64  ω    -95.00 -69.00   0.50    0.05    --  -82.00 117.00-140.69   52
 65  ω    -98.00 -57.00   0.50    0.05    --  -82.00 116.00-154.70   82
 66  ω    -97.00 -52.00   0.50    0.05    --  -82.00 115.00-166.54   90
 67  ω    -93.00 -67.00   0.50    0.05    --  -82.00 113.00 -42.97   52
 68  ω    -73.00 -47.00   0.50    0.05    --  -82.00 123.00 -47.26   52
 69  ω    -92.00 -67.00   0.50    0.05    --  -82.00 109.00 -92.14   50
 70  ω    -76.00 -49.00   0.50    0.05    --  -82.00 109.00  23.42   54
 71  ω    -86.00 -38.00   0.50    0.05    --  -82.00 124.00  41.11   96
 72  ω    -81.00 -44.00   0.50    0.05    --  -82.00 108.00 -16.71   74
 73  ω    -85.00 -60.00   0.50    0.05    --  -82.00 108.00 116.48   50
 74  ω    -65.00 -39.00   0.50    0.05    --  -82.00 124.00 128.62   52
 75  ω    -80.00 -55.00   0.50    0.05    --  -74.26 108.00 158.00   50
 76  ω    -87.00 -62.00   0.50    0.05    --  -78.06 108.00 158.00   50
 77  ω    -53.00 -27.00   0.50    0.05    --  -60.24 108.00 158.00   52
 78  ω    -86.00 -61.00   0.50    0.05    --  -82.00  95.00 -28.70   50
 79  ω    -89.00 -42.00   0.50    0.05    --  -82.00 100.00 -48.89   94
 80  ω    -85.00 -42.00   0.50    0.05    --  -82.00  94.00-166.71   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0327416000
_diffrn_orient_matrix_UB_12      -0.1863442000
_diffrn_orient_matrix_UB_13      0.0159326000
_diffrn_orient_matrix_UB_21      0.0448582000
_diffrn_orient_matrix_UB_22      -0.0701928000
_diffrn_orient_matrix_UB_23      -0.0442613000
_diffrn_orient_matrix_UB_31      0.2288266000
_diffrn_orient_matrix_UB_32      -0.0129048000
_diffrn_orient_matrix_UB_33      0.0109570000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3227
_reflns_number_total             3232
_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 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 1323 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.026(17)
_refine_ls_extinction_coef       0.0076(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.078
_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)+(0.0341P)²+0.2976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0631
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_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 0.10708(14) 0.98402(12) 0.54521(3) 0.0183(2) Uani 1 1 d . . . . .
O2 O 0.36193(15) 1.05218(11) 0.50196(3) 0.0177(2) Uani 1 1 d . . . . .
N1 N 0.28259(17) 0.39844(14) 0.50868(3) 0.0159(2) Uani 1 1 d . . . . .
H1A H 0.368919 0.451452 0.490353 0.024 Uiso 1 1 calc R U . . .
H1B H 0.151175 0.425844 0.502083 0.024 Uiso 1 1 calc R U . . .
H1C H 0.299662 0.281654 0.507072 0.024 Uiso 1 1 calc R U . . .
C1 C 0.27338(19) 0.95002(16) 0.52689(4) 0.0141(3) Uani 1 1 d . . . . .
C2 C 0.3736(2) 0.77338(16) 0.53295(4) 0.0162(3) Uani 1 1 d . . . . .
H2A H 0.509170 0.791233 0.546056 0.019 Uiso 1 1 calc R U . . .
H2B H 0.396919 0.721464 0.504973 0.019 Uiso 1 1 calc R U . . .
C3 C 0.2540(2) 0.64323(16) 0.55965(4) 0.0147(3) Uani 1 1 d . . . . .
H3 H 0.107006 0.649530 0.551188 0.018 Uiso 1 1 calc R U . . .
C4 C 0.3285(2) 0.45801(16) 0.55211(4) 0.0168(3) Uani 1 1 d . . . . .
H4A H 0.477803 0.452488 0.556942 0.020 Uiso 1 1 calc R U . . .
H4B H 0.261571 0.379335 0.572425 0.020 Uiso 1 1 calc R U . . .
C5 C 0.2680(2) 0.68754(17) 0.60639(4) 0.0179(3) Uani 1 1 d . . . . .
H5A H 0.252308 0.814392 0.609566 0.022 Uiso 1 1 calc R U . . .
H5B H 0.406696 0.656854 0.616365 0.022 Uiso 1 1 calc R U . . .
C6 C 0.1113(2) 0.59826(17) 0.63496(4) 0.0190(3) Uani 1 1 d . . . . .
H6 H 0.130637 0.470162 0.632572 0.023 Uiso 1 1 calc R U . . .
C7 C 0.1523(3) 0.6512(2) 0.68039(4) 0.0282(3) Uani 1 1 d . . . . .
H7A H 0.130014 0.776089 0.683516 0.042 Uiso 1 1 calc R U . . .
H7B H 0.293987 0.623257 0.687725 0.042 Uiso 1 1 calc R U . . .
H7C H 0.059255 0.588315 0.699035 0.042 Uiso 1 1 calc R U . . .
C8 C -0.1087(2) 0.6413(2) 0.62248(5) 0.0298(4) Uani 1 1 d . . . . .
H8A H -0.203121 0.590390 0.642898 0.045 Uiso 1 1 calc R U . . .
H8B H -0.137075 0.593741 0.594595 0.045 Uiso 1 1 calc R U . . .
H8C H -0.126696 0.767266 0.621955 0.045 Uiso 1 1 calc R U . . .
O3 O 0.65964(17) 0.08079(14) 0.57971(3) 0.0273(2) Uani 1 1 d . . . . .
O4 O 0.95452(16) 0.13803(14) 0.61242(3) 0.0244(2) Uani 1 1 d . . . . .
H4 H 1.004559 0.099240 0.590062 0.037 Uiso 1 1 calc R U . . .
C9 C 0.7512(2) 0.12964(17) 0.61055(4) 0.0195(3) Uani 1 1 d . . . . .
C10 C 0.6472(2) 0.18306(17) 0.65003(4) 0.0178(3) Uani 1 1 d . . . . .
C11 C 0.4403(2) 0.14628(18) 0.65455(4) 0.0209(3) Uani 1 1 d . . . . .
H11 H 0.368027 0.092120 0.632296 0.025 Uiso 1 1 calc R U . . .
C12 C 0.3391(2) 0.18812(18) 0.69130(4) 0.0222(3) Uani 1 1 d . . . . .
H12 H 0.198701 0.159140 0.694275 0.027 Uiso 1 1 calc R U . . .
C13 C 0.4402(2) 0.27240(18) 0.72413(4) 0.0213(3) Uani 1 1 d . . . . .
C14 C 0.6464(2) 0.31201(18) 0.71896(4) 0.0210(3) Uani 1 1 d . . . . .
H14 H 0.717161 0.371144 0.740676 0.025 Uiso 1 1 calc R U . . .
C15 C 0.7504(2) 0.26659(17) 0.68262(4) 0.0194(3) Uani 1 1 d . . . . .
H15 H 0.891757 0.292350 0.679926 0.023 Uiso 1 1 calc R U . . .
C16 C 0.3286(3) 0.3172(2) 0.76404(5) 0.0281(3) Uani 1 1 d . . . . .
H16A H 0.348234 0.224288 0.784586 0.042 Uiso 1 1 calc R U . . .
H16B H 0.182438 0.330409 0.758108 0.042 Uiso 1 1 calc R U . . .
H16C H 0.382550 0.425952 0.775367 0.042 Uiso 1 1 calc R U . . .


_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 1.2625(16) . ?
O2 C1 1.2611(16) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C4 1.4904(16) . ?
C1 C2 1.5255(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5321(17) . ?
C3 H3 1.0000 . ?
C3 C4 1.5297(17) . ?
C3 C5 1.5325(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5352(18) . ?
C6 H6 1.0000 . ?
C6 C7 1.5295(18) . ?
C6 C8 1.529(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O3 C9 1.2118(17) . ?
O4 H4 0.8400 . ?
O4 C9 1.3330(18) . ?
C9 C10 1.4898(18) . ?
C10 C11 1.390(2) . ?
C10 C15 1.3970(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.399(2) . ?
C13 C14 1.393(2) . ?
C13 C16 1.5078(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3889(19) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C4 N1 H1A 109.5 . . ?
C4 N1 H1B 109.5 . . ?
C4 N1 H1C 109.5 . . ?
O1 C1 C2 119.85(11) . . ?
O2 C1 O1 123.89(12) . . ?
O2 C1 C2 116.20(11) . . ?
C1 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
C1 C2 C3 115.92(11) . . ?
H2A C2 H2B 107.4 . . ?
C3 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
C2 C3 H3 108.0 . . ?
C2 C3 C5 111.33(10) . . ?
C4 C3 C2 111.30(10) . . ?
C4 C3 H3 108.0 . . ?
C4 C3 C5 110.02(10) . . ?
C5 C3 H3 108.0 . . ?
N1 C4 C3 111.74(10) . . ?
N1 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C3 C5 H5A 108.3 . . ?
C3 C5 H5B 108.3 . . ?
C3 C5 C6 115.92(11) . . ?
H5A C5 H5B 107.4 . . ?
C6 C5 H5A 108.3 . . ?
C6 C5 H5B 108.3 . . ?
C5 C6 H6 108.3 . . ?
C7 C6 C5 108.96(11) . . ?
C7 C6 H6 108.3 . . ?
C8 C6 C5 112.12(11) . . ?
C8 C6 H6 108.3 . . ?
C8 C6 C7 110.71(12) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 O4 H4 109.5 . . ?
O3 C9 O4 123.02(13) . . ?
O3 C9 C10 123.13(13) . . ?
O4 C9 C10 113.84(12) . . ?
C11 C10 C9 118.40(12) . . ?
C11 C10 C15 119.16(13) . . ?
C15 C10 C9 122.43(13) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.38(13) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.06(14) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C16 120.63(14) . . ?
C14 C13 C12 118.13(13) . . ?
C14 C13 C16 121.23(14) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.17(14) . . ?
C15 C14 H14 119.4 . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 120.06(14) . . ?
C14 C15 H15 120.0 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 3.55(17) . . . . ?
O2 C1 C2 C3 -173.90(11) . . . . ?
C1 C2 C3 C4 161.35(11) . . . . ?
C1 C2 C3 C5 -75.51(14) . . . . ?
C2 C3 C4 N1 -66.43(14) . . . . ?
C2 C3 C5 C6 164.29(11) . . . . ?
C3 C5 C6 C7 177.81(12) . . . . ?
C3 C5 C6 C8 -59.28(16) . . . . ?
C4 C3 C5 C6 -71.83(14) . . . . ?
C5 C3 C4 N1 169.67(11) . . . . ?
O3 C9 C10 C11 12.0(2) . . . . ?
O3 C9 C10 C15 -168.75(13) . . . . ?
O4 C9 C10 C11 -167.11(12) . . . . ?
O4 C9 C10 C15 12.19(19) . . . . ?
C9 C10 C11 C12 177.75(12) . . . . ?
C9 C10 C15 C14 -179.35(12) . . . . ?
C10 C11 C12 C13 1.9(2) . . . . ?
C11 C10 C15 C14 -0.1(2) . . . . ?
C11 C12 C13 C14 -0.5(2) . . . . ?
C11 C12 C13 C16 -179.92(13) . . . . ?
C12 C13 C14 C15 -1.2(2) . . . . ?
C13 C14 C15 C10 1.4(2) . . . . ?
C15 C10 C11 C12 -1.6(2) . . . . ?
C16 C13 C14 C15 178.27(13) . . . . ?

_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 1.182
_oxdiff_exptl_absorpt_empirical_full_min 0.824
