# Supplementary Information (SI) for Industrial Chemistry & Materials.
# This journal is © Institute of Process Engineering of CAS 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_0628d
_database_code_depnum_ccdc_archive 'CCDC 2491491'
loop_
_audit_author_name
_audit_author_address
'Chen R.'
;Zhejiang University
China
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2026-05-05 downloaded from the CCDC.
;
_audit_creation_date             2025-07-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        Phenylethylamine_D-LA_H2O
_chemical_formula_moiety         'C3 H5 O3, H2 O, C8 H12 N'
_chemical_formula_sum            'C11 H19 N O4'
_chemical_formula_weight         229.27
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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                   8.0904(3)
_cell_length_b                   5.8849(3)
_cell_length_c                   12.8722(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.576(4)
_cell_angle_gamma                90
_cell_volume                     610.91(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2370
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      67.4620
_cell_measurement_theta_min      3.4400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10819
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.004
_diffrn_reflns_theta_min         3.445
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  84.00   0.50    0.50    --   42.80 -29.00 -28.00  262
  2  ω      5.00 135.00   0.50    1.00    --   94.00 -29.00 -28.00  260
  3  ω     53.00 183.00   0.50    1.00    --   94.00  29.00 131.00  260
  4  ω    -47.00  67.00   0.50    0.50    --   42.80 -65.00-150.00  228
  5  ω     13.00 132.00   0.50    0.50    --   42.80  54.00-180.00  238
  6  ω     17.00 132.00   0.50    0.50    --   42.80  77.00 -90.00  230
  7  ω     18.00 132.00   0.50    0.50    --   42.80  65.00   0.00  228
  8  ω    -47.00  67.00   0.50    0.50    --   42.80 -65.00-180.00  228
  9  ω     15.00 132.00   0.50    0.50    --   42.80  82.00-150.00  234
 10  ω    -47.00  67.00   0.50    0.50    --   42.80 -65.00 150.00  228
 11  ω     17.00 132.00   0.50    0.50    --   42.80  77.00 -60.00  230
 12  ω     18.00 132.00   0.50    0.50    --   42.80  65.00   0.00  228
 13  ω     15.00 132.00   0.50    0.50    --   42.80  59.00-110.39  234
 14  ω     17.00 132.00   0.50    0.50    --   42.80  77.00-120.00  230
 15  ω     18.00 132.00   0.50    0.50    --   42.80  65.00 -90.00  228
 16  ω     70.00 183.00   0.50    1.00    --   94.00  68.00 -90.00  226
 17  ω     67.00 183.00   0.50    1.00    --   94.00  59.00-180.00  232
 18  ω     67.00 183.00   0.50    1.00    --   94.00  82.00 -90.00  232
 19  ω     67.00 183.00   0.50    1.00    --   94.00  82.00-180.00  232
 20  ω     67.00 183.00   0.50    1.00    --   94.00  82.00-120.00  232
 21  ω     68.00 183.00   0.50    1.00    --   94.00  60.00-111.66  230
 22  ω      5.00 118.00   0.50    1.00    --   94.00 -68.00   0.00  226
 23  ω      5.00 123.00   0.50    1.00    --   94.00 -50.00 150.00  236
 24  ω      5.00 123.00   0.50    1.00    --   94.00 -50.00-150.00  236
 25  ω     70.00 183.00   0.50    1.00    --   94.00  66.00 174.98  226
 26  ω     70.00 183.00   0.50    1.00    --   94.00  68.00-120.00  226
 27  ω     69.00 183.00   0.50    1.00    --   94.00  77.00 -90.00  228
 28  ω     70.00 183.00   0.50    1.00    --   94.00  68.00-180.00  226
 29  ω      5.00 183.00   0.50    1.00    --   94.00  25.00 -90.00  356
 30  ω     65.00 183.00   0.50    1.00    --   94.00  50.00 -30.00  236
 31  ω     68.00 183.00   0.50    1.00    --   94.00  80.00-159.45  230
 32  ω     68.00 183.00   0.50    1.00    --   94.00  80.00-159.45  230
 33  ω     67.00 183.00   0.50    1.00    --   94.00  82.00-150.00  232
 34  ω     69.00 183.00   0.50    1.00    --   94.00  77.00-120.00  228
 35  ω     67.00 183.00   0.50    1.00    --   94.00  59.00-120.00  232
 36  ω      5.00 121.00   0.50    1.00    --   94.00 -82.00-180.00  232
 37  ω     67.00 104.00   0.50    1.00    --   94.00  54.00-122.23   74
 38  ω     67.00  95.00   0.50    1.00    --   94.00  52.00-126.37   56
 39  ω     69.00  95.00   0.50    1.00    --   94.00  56.00-138.26   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1206425000
_diffrn_orient_matrix_UB_12      0.0610314000
_diffrn_orient_matrix_UB_13      0.0825027000
_diffrn_orient_matrix_UB_21      -0.1291373000
_diffrn_orient_matrix_UB_22      0.0789041000
_diffrn_orient_matrix_UB_23      -0.0868592000
_diffrn_orient_matrix_UB_31      -0.0723299000
_diffrn_orient_matrix_UB_32      -0.2421907000
_diffrn_orient_matrix_UB_33      -0.0075873000
_diffrn_oxdiff_digest_hkl        
;
01f83f7d64c853db6d0b1b0098cb083a775ec7
;
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                1678
_reflns_number_total             2131
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 554 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2131
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.090
_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)+(0.0478P)²+0.0539P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1140
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O4(H4a,H4b)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C10(H10)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C7(H7), C6(H6), C8(H8)
2.d Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C3(H3a,H3b,H3c)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), N1(H1a)
;
_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
O1 O 0.0665(3) 0.4510(5) 0.3649(2) 0.0297(8) Uani 1 1 d . . . . .
O2 O 0.2635(3) 0.2951(5) 0.4739(2) 0.0299(8) Uani 1 1 d . . . . .
O4 O 0.4422(3) 0.6003(6) 0.5928(2) 0.0346(8) Uani 1 1 d G . . . .
H4A H 0.387251 0.517810 0.545729 0.052 Uiso 1 1 d G U . . .
H4B H 0.534151 0.633551 0.565429 0.052 Uiso 1 1 d G U . . .
O3 O 0.1692(4) -0.1196(6) 0.4322(2) 0.0347(8) Uani 1 1 d . . . . .
H3 H 0.139047 -0.249371 0.411065 0.052 Uiso 1 1 calc R U . . .
N1 N 0.2747(4) 0.9875(7) 0.6427(3) 0.0275(9) Uani 1 1 d . . . . .
H1A H 0.320715 0.863763 0.629938 0.041 Uiso 1 1 calc R U . . .
C1 C 0.1390(4) 0.2824(8) 0.4068(3) 0.0255(10) Uani 1 1 d . . . . .
C4 C 0.3183(4) 0.9280(8) 0.8323(3) 0.0264(10) Uani 1 1 d . . . . .
C2 C 0.0741(4) 0.0479(8) 0.3752(3) 0.0275(11) Uani 1 1 d . . . . .
H2 H -0.043616 0.035698 0.392994 0.033 Uiso 1 1 calc R U . . .
C10 C 0.3525(4) 1.0836(9) 0.7426(3) 0.0284(10) Uani 1 1 d . . . . .
H10 H 0.299825 1.234072 0.754527 0.034 Uiso 1 1 calc R U . . .
C9 C 0.2037(4) 0.9934(9) 0.9023(3) 0.0325(11) Uani 1 1 d . . . . .
H9 H 0.148686 1.135552 0.893666 0.039 Uiso 1 1 calc R U . . .
C5 C 0.3982(5) 0.7205(9) 0.8484(3) 0.0325(11) Uani 1 1 d . . . . .
H5 H 0.476977 0.673119 0.801989 0.039 Uiso 1 1 calc R U . . .
C7 C 0.2497(5) 0.6476(10) 0.9987(3) 0.0379(13) Uani 1 1 d . . . . .
H7 H 0.226033 0.551744 1.055014 0.045 Uiso 1 1 calc R U . . .
C11 C 0.5360(4) 1.1231(9) 0.7309(3) 0.0332(11) Uani 1 1 d . . . . .
H11A H 0.590769 0.977031 0.720977 0.050 Uiso 1 1 calc R U . . .
H11B H 0.586733 1.196939 0.793867 0.050 Uiso 1 1 calc R U . . .
H11C H 0.548811 1.220777 0.670420 0.050 Uiso 1 1 calc R U . . .
C6 C 0.3650(5) 0.5816(9) 0.9309(3) 0.0359(11) Uani 1 1 d . . . . .
H6 H 0.421501 0.440829 0.940937 0.043 Uiso 1 1 calc R U . . .
C8 C 0.1695(5) 0.8523(10) 0.9843(3) 0.0396(13) Uani 1 1 d . . . . .
H8 H 0.090086 0.897583 1.030731 0.047 Uiso 1 1 calc R U . . .
C3 C 0.0792(5) 0.0146(9) 0.2586(3) 0.0369(12) Uani 1 1 d . . . . .
H3A H 0.193025 0.035854 0.239413 0.055 Uiso 1 1 calc R U . . .
H3B H 0.006271 0.125865 0.221488 0.055 Uiso 1 1 calc R U . . .
H3C H 0.041735 -0.139285 0.239651 0.055 Uiso 1 1 calc R U . . .
H1B H 0.151(6) 0.957(10) 0.652(4) 0.050(13) Uiso 1 1 d . . . . .
H1C H 0.272(6) 1.092(11) 0.578(4) 0.055(15) 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 1.253(5) . ?
O2 C1 1.276(4) . ?
O4 H4A 0.8701 . ?
O4 H4B 0.8700 . ?
O3 H3 0.8400 . ?
O3 C2 1.418(5) . ?
N1 H1A 0.8400 . ?
N1 C10 1.496(5) . ?
N1 H1B 1.03(5) . ?
N1 H1C 1.03(6) . ?
C1 C2 1.520(6) . ?
C4 C10 1.516(6) . ?
C4 C9 1.398(6) . ?
C4 C5 1.390(7) . ?
C2 H2 1.0000 . ?
C2 C3 1.517(6) . ?
C10 H10 1.0000 . ?
C10 C11 1.522(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.388(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(6) . ?
C7 H7 0.9500 . ?
C7 C6 1.384(7) . ?
C7 C8 1.374(8) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C6 H6 0.9500 . ?
C8 H8 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 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
H4A O4 H4B 104.5 . . ?
C2 O3 H3 109.5 . . ?
H1A N1 H1B 108.8 . . ?
H1A N1 H1C 109.7 . . ?
C10 N1 H1A 109.5 . . ?
C10 N1 H1B 108(3) . . ?
C10 N1 H1C 117(3) . . ?
H1B N1 H1C 104(4) . . ?
O1 C1 O2 124.2(4) . . ?
O1 C1 C2 117.7(3) . . ?
O2 C1 C2 118.1(4) . . ?
C9 C4 C10 119.7(4) . . ?
C5 C4 C10 122.3(4) . . ?
C5 C4 C9 118.0(4) . . ?
O3 C2 C1 109.4(3) . . ?
O3 C2 H2 108.6 . . ?
O3 C2 C3 111.4(4) . . ?
C1 C2 H2 108.6 . . ?
C3 C2 C1 110.2(4) . . ?
C3 C2 H2 108.6 . . ?
N1 C10 C4 109.6(4) . . ?
N1 C10 H10 108.1 . . ?
N1 C10 C11 108.7(3) . . ?
C4 C10 H10 108.1 . . ?
C4 C10 C11 114.0(3) . . ?
C11 C10 H10 108.1 . . ?
C4 C9 H9 119.7 . . ?
C8 C9 C4 120.6(5) . . ?
C8 C9 H9 119.7 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C8 C7 C6 119.7(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C6 C7 120.0(5) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.4(4) . . ?
C7 C8 H8 119.8 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?


_olex2_submission_original_sample_id D
_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 7.625
_oxdiff_exptl_absorpt_empirical_full_min 0.595
####################################################################### 
# 
# 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_0628-l_auto
_database_code_depnum_ccdc_archive 'CCDC 2491490'
loop_
_audit_author_name
_audit_author_address
'Chen R.'
;Zhejiang University
China
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2026-05-05 downloaded from the CCDC.
;
_audit_creation_date             2024-06-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
rdchen@zju.edu.cn
_chemical_name_common            ?
_chemical_name_systematic        Phenylethylamine_L-LA
_chemical_formula_moiety         'C8 H12 N, C3 H5 O3'
_chemical_formula_sum            'C11 H17 N O3'
_chemical_formula_weight         211.25
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c h o n'
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                   6.84664(7)
_cell_length_b                   6.98240(8)
_cell_length_c                   24.3030(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1161.83(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6327
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      67.9170
_cell_measurement_theta_min      3.6300
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9202
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_min         3.637
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     14.00 131.00   0.50    0.50    --   42.50  45.00  66.00  234
  2  ω    -46.00  71.00   0.50    0.50    --   42.50 -45.00 -83.00  234
  3  ω      5.00 123.00   0.50    1.00    --   94.00 -45.00 -83.00  236
  4  ω     65.00 183.00   0.50    1.00    --   94.00  45.00  66.00  236
  5  ω     18.00 131.00   0.50    0.50    --   42.50  77.00   0.00  226
  6  ω     14.00 131.00   0.50    0.50    --   42.50  43.00-150.00  234
  7  ω    -46.00  66.00   0.50    0.50    --   42.50 -65.00-180.00  224
  8  ω    -46.00  66.00   0.50    0.50    --   42.50 -65.00-120.00  224
  9  ω     19.00 131.00   0.50    0.50    --   42.50  65.00-120.00  224
 10  ω      5.00 183.00   0.50    1.00    --   94.00 -25.00  30.00  356
 11  ω      5.00 121.00   0.50    1.00    --   94.00 -82.00 -90.00  232
 12  ω      5.00 118.00   0.50    1.00    --   94.00 -68.00 -60.00  226
 13  ω      5.00 118.00   0.50    1.00    --   94.00 -68.00  90.00  226
 14  ω     70.00 183.00   0.50    1.00    --   94.00  68.00-180.00  226
 15  ω      5.00 118.00   0.50    1.00    --   94.00 -68.00  60.00  226
 16  ω      5.00 124.00   0.50    1.00    --   94.00 -42.00  90.00  238
 17  ω     19.00 126.00   0.50    0.50    --   42.50  65.00 120.00  214
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0811237000
_diffrn_orient_matrix_UB_12      0.1222672000
_diffrn_orient_matrix_UB_13      0.0475670000
_diffrn_orient_matrix_UB_21      -0.1964274000
_diffrn_orient_matrix_UB_22      -0.0181939000
_diffrn_orient_matrix_UB_23      0.0304868000
_diffrn_orient_matrix_UB_31      0.0739220000
_diffrn_orient_matrix_UB_32      -0.1827553000
_diffrn_orient_matrix_UB_33      0.0287443000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2023
_reflns_number_total             2122
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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         0.148
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_coef       0.0027(6)
_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   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.071
_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)+(0.0352P)²+0.1142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0706
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C10(H10), C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C3(H3A,H3B,H3C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 -0.45734(19) -0.90408(17) -0.19701(5) 0.0327(3) Uani 1 1 d . . . . .
H3 H -0.514990 -0.922448 -0.227058 0.049 Uiso 1 1 calc R U . . .
O2 O -0.12681(17) -0.68433(18) -0.20021(5) 0.0325(3) Uani 1 1 d . . . . .
N1 N -1.0797(2) -0.1004(2) -0.20289(5) 0.0243(3) Uani 1 1 d . . . . .
H1A H -1.152486 -0.208887 -0.199788 0.036 Uiso 1 1 calc R U . . .
H1B H -1.011557 -0.103296 -0.235033 0.036 Uiso 1 1 calc R U . . .
H1C H -1.159818 0.003589 -0.202611 0.036 Uiso 1 1 calc R U . . .
O1 O -0.3102(2) -0.42502(18) -0.21303(5) 0.0368(3) Uani 1 1 d . . . . .
C4 C -1.0527(3) -0.0692(3) -0.10200(6) 0.0273(4) Uani 1 1 d . . . . .
C5 C -1.0287(3) 0.0914(3) -0.06927(7) 0.0318(4) Uani 1 1 d . . . . .
H5 H -0.942503 0.190271 -0.080763 0.038 Uiso 1 1 calc R U . . .
C9 C -1.1795(3) -0.2109(3) -0.08447(8) 0.0394(5) Uani 1 1 d . . . . .
H9 H -1.197372 -0.322447 -0.106291 0.047 Uiso 1 1 calc R U . . .
C11 C -0.8045(3) -0.2602(3) -0.15618(8) 0.0378(5) Uani 1 1 d . . . . .
H11A H -0.881615 -0.377777 -0.152709 0.057 Uiso 1 1 calc R U . . .
H11B H -0.712637 -0.251203 -0.125368 0.057 Uiso 1 1 calc R U . . .
H11C H -0.731815 -0.262576 -0.190914 0.057 Uiso 1 1 calc R U . . .
C10 C -0.9399(2) -0.0881(3) -0.15550(6) 0.0269(4) Uani 1 1 d . . . . .
H10 H -0.858818 0.029803 -0.160326 0.032 Uiso 1 1 calc R U . . .
C6 C -1.1291(3) 0.1100(3) -0.01971(7) 0.0368(4) Uani 1 1 d . . . . .
H6 H -1.110363 0.220356 0.002529 0.044 Uiso 1 1 calc R U . . .
C7 C -1.2555(3) -0.0316(3) -0.00300(7) 0.0392(5) Uani 1 1 d . . . . .
H7 H -1.324900 -0.018944 0.030654 0.047 Uiso 1 1 calc R U . . .
C8 C -1.2811(3) -0.1918(3) -0.03528(8) 0.0458(5) Uani 1 1 d . . . . .
H8 H -1.368531 -0.289600 -0.023858 0.055 Uiso 1 1 calc R U . . .
C3 C -0.4949(3) -0.6916(3) -0.12068(7) 0.0361(4) Uani 1 1 d . . . . .
H3A H -0.615269 -0.756995 -0.109625 0.054 Uiso 1 1 calc R U . . .
H3B H -0.502410 -0.556295 -0.110146 0.054 Uiso 1 1 calc R U . . .
H3C H -0.383047 -0.751453 -0.102305 0.054 Uiso 1 1 calc R U . . .
C2 C -0.4699(3) -0.7070(2) -0.18260(6) 0.0256(4) Uani 1 1 d . . . . .
H2 H -0.586127 -0.649110 -0.201144 0.031 Uiso 1 1 calc R U . . .
C1 C -0.2871(2) -0.5991(2) -0.20010(6) 0.0248(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 H3 0.8400 . ?
O3 C2 1.422(2) . ?
O2 C1 1.248(2) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C10 1.500(2) . ?
O1 C1 1.265(2) . ?
C4 C5 1.385(3) . ?
C4 C9 1.384(3) . ?
C4 C10 1.518(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.389(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C10 1.517(3) . ?
C10 H10 1.0000 . ?
C6 H6 0.9500 . ?
C6 C7 1.375(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(3) . ?
C8 H8 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 C2 1.518(2) . ?
C2 H2 1.0000 . ?
C2 C1 1.522(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
C2 O3 H3 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C10 N1 H1A 109.5 . . ?
C10 N1 H1B 109.5 . . ?
C10 N1 H1C 109.5 . . ?
C5 C4 C10 120.14(16) . . ?
C9 C4 C5 118.47(16) . . ?
C9 C4 C10 121.39(16) . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.89(18) . . ?
C6 C5 H5 119.6 . . ?
C4 C9 H9 119.7 . . ?
C4 C9 C8 120.67(18) . . ?
C8 C9 H9 119.7 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
N1 C10 C4 109.77(13) . . ?
N1 C10 C11 109.65(14) . . ?
N1 C10 H10 108.1 . . ?
C4 C10 H10 108.1 . . ?
C11 C10 C4 112.88(14) . . ?
C11 C10 H10 108.1 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 119.94(18) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.70(17) . . ?
C8 C7 H7 120.1 . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.32(19) . . ?
C7 C8 H8 119.8 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
O3 C2 C3 108.64(15) . . ?
O3 C2 H2 109.2 . . ?
O3 C2 C1 111.14(14) . . ?
C3 C2 H2 109.2 . . ?
C3 C2 C1 109.54(14) . . ?
C1 C2 H2 109.2 . . ?
O2 C1 O1 124.59(16) . . ?
O2 C1 C2 119.16(15) . . ?
O1 C1 C2 116.23(16) . . ?

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 C2 C1 O2 -32.00(19) . . . . ?
O3 C2 C1 O1 148.87(14) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C4 C9 C8 C7 -0.5(3) . . . . ?
C5 C4 C9 C8 0.3(3) . . . . ?
C5 C4 C10 N1 -118.89(17) . . . . ?
C5 C4 C10 C11 118.46(19) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C9 C4 C5 C6 0.2(3) . . . . ?
C9 C4 C10 N1 61.7(2) . . . . ?
C9 C4 C10 C11 -61.0(2) . . . . ?
C10 C4 C5 C6 -179.20(17) . . . . ?
C10 C4 C9 C8 179.75(19) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C3 C2 C1 O2 88.05(18) . . . . ?
C3 C2 C1 O1 -91.08(18) . . . . ?


_olex2_submission_original_sample_id L
_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 1.128
_oxdiff_exptl_absorpt_empirical_full_min 0.821
####################################################################### 
# 
# 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_syy
_database_code_depnum_ccdc_archive 'CCDC 2491485'
loop_
_audit_author_name
_audit_author_address
'Chen R.'
;Zhejiang University
China
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2026-05-05 downloaded from the CCDC.
;
_audit_creation_date             2024-04-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
rdchen@zju.edu.cn
_chemical_name_common            ?
_chemical_name_systematic        Phenylpropylamine_L-LA
_chemical_formula_moiety         'C9 H14 N, C3 H5 O3'
_chemical_formula_sum            'C12 H19 N O3'
_chemical_formula_weight         225.28
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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                   5.75430(10)
_cell_length_b                   13.5274(2)
_cell_length_c                   32.4808(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2528.33(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6614
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      67.6840
_cell_measurement_theta_min      2.7020
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            20713
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.362
_diffrn_reflns_theta_min         2.721
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00 131.00   0.50    1.00    --   42.50  67.00  -9.00  224
  2  ω    -46.00  66.00   0.50    1.00    --   42.50 -67.00-143.00  224
  3  ω    -46.00  71.00   0.50    1.00    --   42.50 -54.00  26.00  234
  4  ω      5.00 118.00   0.50    8.00    --   94.00 -67.00-143.00  226
  5  ω      5.00 123.00   0.50    8.00    --   94.00 -54.00  26.00  236
  6  ω     65.00 183.00   0.50    8.00    --   94.00  54.00 170.00  236
  7  ω     70.00 183.00   0.50    8.00    --   94.00  67.00  -9.00  226
  8  ω     19.00 131.00   0.50    1.00    --   42.50  65.00-150.00  224
  9  ω     14.00 131.00   0.50    1.00    --   42.50  54.00 170.00  234
 10  ω      9.00 131.00   0.50    1.00    --   42.50  32.00 -30.00  244
 11  ω     19.00 131.00   0.50    1.00    --   42.50  65.00 -90.00  224
 12  ω      5.00 124.00   0.50    8.00    --   94.00 -42.00-180.00  238
 13  ω      5.00 121.00   0.50    8.00    --   94.00 -82.00   0.00  232
 14  ω     70.00 183.00   0.50    8.00    --   94.00  68.00  30.00  226
 15  ω     64.00 183.00   0.50    8.00    --   94.00  42.00  90.00  238
 16  ω    -46.00  69.00   0.50    1.00    --   42.50 -82.00-180.00  230
 17  ω     18.00 131.00   0.50    1.00    --   42.50  77.00 120.00  226
 18  ω     18.00  52.00   0.50    1.00    --   42.50  77.00  30.00   68
 19  ω     16.00 131.00   0.50    1.00    --   42.50  82.00  60.00  230
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0253310000
_diffrn_orient_matrix_UB_12      0.0206367000
_diffrn_orient_matrix_UB_13      -0.0464452000
_diffrn_orient_matrix_UB_21      0.1713702000
_diffrn_orient_matrix_UB_22      -0.0844746000
_diffrn_orient_matrix_UB_23      -0.0094079000
_diffrn_orient_matrix_UB_31      -0.2040784000
_diffrn_orient_matrix_UB_32      -0.0735314000
_diffrn_orient_matrix_UB_33      -0.0021637000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.610
_reflns_Friedel_fraction_full    0.859
_reflns_Friedel_fraction_max     0.847
_reflns_number_gt                3669
_reflns_number_total             4323
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1241 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0554
_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)+(0.0795P)²+1.3587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.1546
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C20(H20), C16(H16), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C15(H15), C12(H12), C11(H11), C13(H13), C5(H5), C3(H3),
 C14(H14), C4(H4)
2.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2A,H2B,H2C), C21(H21A,H21B,H21C), C9(H9A,H9B,H9C),
 C18(H18A,H18B,H18C), C24(H24A,H24B,H24C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3A), O5(H5A)
;
_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 0.1327(5) 0.3767(2) 0.32310(8) 0.0304(6) Uani 1 1 d . . . . .
H3A H 0.160336 0.395814 0.298979 0.046 Uiso 1 1 calc R U . . .
O2 O 0.4899(5) 0.2506(2) 0.34733(9) 0.0362(7) Uani 1 1 d . . . . .
O1 O 0.2212(5) 0.1444(2) 0.36885(9) 0.0353(7) Uani 1 1 d . . . . .
O4 O 0.3490(5) 0.4636(2) 0.26114(8) 0.0377(7) Uani 1 1 d . . . . .
O6 O 0.2112(5) 0.4805(2) 0.19759(9) 0.0384(7) Uani 1 1 d . . . . .
O5 O 0.7835(5) 0.4685(3) 0.23808(8) 0.0373(7) Uani 1 1 d . . . . .
H5A H 0.917910 0.472610 0.228116 0.056 Uiso 1 1 calc R U . . .
N1 N 0.6575(6) 0.4366(2) 0.32418(10) 0.0282(7) Uani 1 1 d . . . . .
H1A H 0.612283 0.447019 0.297681 0.034 Uiso 1 1 calc R U . . .
H1B H 0.591982 0.379769 0.333678 0.034 Uiso 1 1 calc R U . . .
H1C H 0.815023 0.431313 0.325254 0.034 Uiso 1 1 calc R U . . .
N2 N 0.2421(6) 0.5891(2) 0.12610(10) 0.0292(7) Uani 1 1 d . . . . .
H2A H 0.089240 0.606088 0.124634 0.035 Uiso 1 1 calc R U . . .
H2B H 0.328310 0.643792 0.131895 0.035 Uiso 1 1 calc R U . . .
H2C H 0.262396 0.543378 0.146313 0.035 Uiso 1 1 calc R U . . .
C22 C 0.2808(7) 0.2196(3) 0.34882(12) 0.0287(9) Uani 1 1 d . . . . .
C19 C 0.3740(7) 0.4699(3) 0.22327(12) 0.0285(8) Uani 1 1 d . . . . .
C7 C 0.5809(8) 0.5210(3) 0.35019(13) 0.0343(9) Uani 1 1 d . . . . .
H7 H 0.407373 0.522877 0.348769 0.041 Uiso 1 1 calc R U . . .
C20 C 0.6191(7) 0.4604(3) 0.20568(11) 0.0303(9) Uani 1 1 d . . . . .
H20 H 0.645996 0.514881 0.185430 0.036 Uiso 1 1 calc R U . . .
C10 C 0.2256(7) 0.4438(3) 0.07885(11) 0.0320(9) Uani 1 1 d . . . . .
C16 C 0.3176(7) 0.5470(3) 0.08600(11) 0.0326(9) Uani 1 1 d . . . . .
H16 H 0.491059 0.542512 0.086626 0.039 Uiso 1 1 calc R U . . .
C1 C 0.6442(8) 0.5059(3) 0.39488(12) 0.0352(10) Uani 1 1 d . . . . .
C23 C 0.0977(7) 0.2722(3) 0.32321(14) 0.0367(10) Uani 1 1 d . . . . .
H23 H -0.056758 0.259115 0.336202 0.044 Uiso 1 1 calc R U . . .
C2 C 0.8500(8) 0.4601(4) 0.40762(13) 0.0378(10) Uani 1 1 d . . . . .
H2 H 0.956842 0.436126 0.387681 0.045 Uiso 1 1 calc R U . . .
C17 C 0.2529(9) 0.6166(3) 0.05107(13) 0.0396(10) Uani 1 1 d . . . . .
H17A H 0.085440 0.632492 0.053323 0.048 Uiso 1 1 calc R U . . .
H17B H 0.276446 0.581608 0.024623 0.048 Uiso 1 1 calc R U . . .
C6 C 0.4945(9) 0.5397(4) 0.42508(14) 0.0432(11) Uani 1 1 d . . . . .
H6 H 0.353314 0.570514 0.417007 0.052 Uiso 1 1 calc R U . . .
C15 C 0.0102(8) 0.4120(4) 0.09332(14) 0.0395(11) Uani 1 1 d . . . . .
H15 H -0.084043 0.455241 0.109226 0.047 Uiso 1 1 calc R U . . .
C12 C 0.2764(10) 0.2853(3) 0.04599(14) 0.0465(12) Uani 1 1 d . . . . .
H12 H 0.368272 0.242404 0.029522 0.056 Uiso 1 1 calc R U . . .
C11 C 0.3549(9) 0.3792(3) 0.05500(14) 0.0413(11) Uani 1 1 d . . . . .
H11 H 0.501182 0.399996 0.044586 0.050 Uiso 1 1 calc R U . . .
C13 C 0.0645(10) 0.2537(4) 0.06089(15) 0.0458(12) Uani 1 1 d . . . . .
H13 H 0.009647 0.188974 0.054965 0.055 Uiso 1 1 calc R U . . .
C5 C 0.5424(10) 0.5302(4) 0.46628(15) 0.0521(14) Uani 1 1 d . . . . .
H5 H 0.436994 0.555194 0.486243 0.062 Uiso 1 1 calc R U . . .
C8 C 0.6679(9) 0.6183(3) 0.33212(15) 0.0432(11) Uani 1 1 d . . . . .
H8A H 0.601155 0.626165 0.304213 0.052 Uiso 1 1 calc R U . . .
H8B H 0.608307 0.673267 0.349275 0.052 Uiso 1 1 calc R U . . .
C21 C 0.6414(9) 0.3616(4) 0.18378(15) 0.0464(12) Uani 1 1 d . . . . .
H21A H 0.801467 0.353058 0.174141 0.070 Uiso 1 1 calc R U . . .
H21B H 0.535230 0.360018 0.160196 0.070 Uiso 1 1 calc R U . . .
H21C H 0.601758 0.308156 0.202882 0.070 Uiso 1 1 calc R U . . .
C3 C 0.8985(9) 0.4496(4) 0.44899(13) 0.0474(12) Uani 1 1 d . . . . .
H3 H 1.038799 0.418210 0.457179 0.057 Uiso 1 1 calc R U . . .
C14 C -0.0659(9) 0.3174(4) 0.08445(15) 0.0452(12) Uani 1 1 d . . . . .
H14 H -0.211674 0.295858 0.094875 0.054 Uiso 1 1 calc R U . . .
C4 C 0.7473(11) 0.4837(4) 0.47863(14) 0.0541(15) Uani 1 1 d . . . . .
H4 H 0.781908 0.475683 0.507028 0.065 Uiso 1 1 calc R U . . .
C9 C 0.9299(9) 0.6278(4) 0.32909(17) 0.0508(13) Uani 1 1 d . . . . .
H9A H 0.990235 0.577297 0.310296 0.076 Uiso 1 1 calc R U . . .
H9B H 0.998907 0.618747 0.356417 0.076 Uiso 1 1 calc R U . . .
H9C H 0.970019 0.693589 0.318604 0.076 Uiso 1 1 calc R U . . .
C18 C 0.3900(13) 0.7132(4) 0.04998(16) 0.0576(15) Uani 1 1 d . . . . .
H18A H 0.343965 0.751668 0.025742 0.086 Uiso 1 1 calc R U . . .
H18B H 0.556568 0.698591 0.048551 0.086 Uiso 1 1 calc R U . . .
H18C H 0.357325 0.751439 0.074955 0.086 Uiso 1 1 calc R U . . .
C24 C 0.0909(14) 0.2307(4) 0.28023(18) 0.072(2) Uani 1 1 d . . . . .
H24A H -0.020586 0.268243 0.263644 0.108 Uiso 1 1 calc R U . . .
H24B H 0.043294 0.161175 0.281282 0.108 Uiso 1 1 calc R U . . .
H24C H 0.245682 0.235577 0.267799 0.108 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
O3 H3A 0.8400 . ?
O3 C23 1.428(5) . ?
O2 C22 1.276(5) . ?
O1 C22 1.254(5) . ?
O4 C19 1.241(5) . ?
O6 C19 1.262(5) . ?
O5 H5A 0.8400 . ?
O5 C20 1.419(5) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C7 1.488(5) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N2 C16 1.487(5) . ?
C22 C23 1.520(6) . ?
C19 C20 1.527(5) . ?
C7 H7 1.0000 . ?
C7 C1 1.511(6) . ?
C7 C8 1.526(6) . ?
C20 H20 1.0000 . ?
C20 C21 1.519(6) . ?
C10 C16 1.511(6) . ?
C10 C15 1.394(6) . ?
C10 C11 1.385(6) . ?
C16 H16 1.0000 . ?
C16 C17 1.521(6) . ?
C1 C2 1.399(6) . ?
C1 C6 1.383(6) . ?
C23 H23 1.0000 . ?
C23 C24 1.505(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.527(7) . ?
C6 H6 0.9500 . ?
C6 C5 1.372(7) . ?
C15 H15 0.9500 . ?
C15 C14 1.384(7) . ?
C12 H12 0.9500 . ?
C12 C11 1.379(7) . ?
C12 C13 1.380(8) . ?
C11 H11 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.375(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.395(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.517(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.377(7) . ?
C14 H14 0.9500 . ?
C4 H4 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C23 O3 H3A 109.5 . . ?
C20 O5 H5A 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C7 N1 H1A 109.5 . . ?
C7 N1 H1B 109.5 . . ?
C7 N1 H1C 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C16 N2 H2A 109.5 . . ?
C16 N2 H2B 109.5 . . ?
C16 N2 H2C 109.5 . . ?
O2 C22 C23 118.6(4) . . ?
O1 C22 O2 123.0(4) . . ?
O1 C22 C23 118.3(4) . . ?
O4 C19 O6 125.2(4) . . ?
O4 C19 C20 118.2(3) . . ?
O6 C19 C20 116.6(3) . . ?
N1 C7 H7 106.8 . . ?
N1 C7 C1 111.7(3) . . ?
N1 C7 C8 110.3(3) . . ?
C1 C7 H7 106.8 . . ?
C1 C7 C8 114.1(4) . . ?
C8 C7 H7 106.8 . . ?
O5 C20 C19 109.4(3) . . ?
O5 C20 H20 109.1 . . ?
O5 C20 C21 111.0(4) . . ?
C19 C20 H20 109.1 . . ?
C21 C20 C19 109.1(4) . . ?
C21 C20 H20 109.1 . . ?
C15 C10 C16 123.0(4) . . ?
C11 C10 C16 118.8(4) . . ?
C11 C10 C15 118.2(4) . . ?
N2 C16 C10 112.7(3) . . ?
N2 C16 H16 107.3 . . ?
N2 C16 C17 110.1(3) . . ?
C10 C16 H16 107.3 . . ?
C10 C16 C17 111.8(3) . . ?
C17 C16 H16 107.3 . . ?
C2 C1 C7 123.2(4) . . ?
C6 C1 C7 119.1(4) . . ?
C6 C1 C2 117.6(4) . . ?
O3 C23 C22 111.6(3) . . ?
O3 C23 H23 107.6 . . ?
O3 C23 C24 111.8(4) . . ?
C22 C23 H23 107.6 . . ?
C24 C23 C22 110.5(4) . . ?
C24 C23 H23 107.6 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.8 . . ?
C16 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
C16 C17 C18 114.9(4) . . ?
H17A C17 H17B 107.5 . . ?
C18 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
C1 C6 H6 118.8 . . ?
C5 C6 C1 122.4(5) . . ?
C5 C6 H6 118.8 . . ?
C10 C15 H15 120.1 . . ?
C14 C15 C10 119.8(4) . . ?
C14 C15 H15 120.1 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(5) . . ?
C13 C12 H12 120.0 . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.6(5) . . ?
C12 C11 H11 119.2 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.9(5) . . ?
C14 C13 H13 120.6 . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.5(5) . . ?
C4 C5 H5 120.3 . . ?
C7 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 C7 115.1(4) . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(5) . . ?
C4 C3 H3 119.4 . . ?
C15 C14 H14 119.2 . . ?
C13 C14 C15 121.5(5) . . ?
C13 C14 H14 119.2 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O2 C22 C23 O3 -38.9(5) . . . . ?
O2 C22 C23 C24 86.1(5) . . . . ?
O1 C22 C23 O3 144.6(4) . . . . ?
O1 C22 C23 C24 -90.3(5) . . . . ?
O4 C19 C20 O5 -13.5(6) . . . . ?
O4 C19 C20 C21 108.2(4) . . . . ?
O6 C19 C20 O5 168.7(4) . . . . ?
O6 C19 C20 C21 -69.7(5) . . . . ?
N1 C7 C1 C2 36.3(6) . . . . ?
N1 C7 C1 C6 -144.5(4) . . . . ?
N1 C7 C8 C9 -60.9(5) . . . . ?
N2 C16 C17 C18 69.2(5) . . . . ?
C7 C1 C2 C3 179.3(4) . . . . ?
C7 C1 C6 C5 -178.7(4) . . . . ?
C10 C16 C17 C18 -164.6(4) . . . . ?
C10 C15 C14 C13 -1.2(7) . . . . ?
C16 C10 C15 C14 177.9(4) . . . . ?
C16 C10 C11 C12 -177.5(4) . . . . ?
C1 C7 C8 C9 65.8(6) . . . . ?
C1 C2 C3 C4 -0.1(7) . . . . ?
C1 C6 C5 C4 -1.0(8) . . . . ?
C2 C1 C6 C5 0.5(7) . . . . ?
C2 C3 C4 C5 -0.4(8) . . . . ?
C6 C1 C2 C3 0.1(7) . . . . ?
C6 C5 C4 C3 1.0(7) . . . . ?
C15 C10 C16 N2 33.1(5) . . . . ?
C15 C10 C16 C17 -91.6(5) . . . . ?
C15 C10 C11 C12 -0.8(7) . . . . ?
C12 C13 C14 C15 0.3(8) . . . . ?
C11 C10 C16 N2 -150.4(4) . . . . ?
C11 C10 C16 C17 84.8(5) . . . . ?
C11 C10 C15 C14 1.4(6) . . . . ?
C11 C12 C13 C14 0.4(7) . . . . ?
C13 C12 C11 C10 -0.1(7) . . . . ?
C8 C7 C1 C2 -89.6(5) . . . . ?
C8 C7 C1 C6 89.6(5) . . . . ?


_olex2_submission_original_sample_id L
_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 1.368
_oxdiff_exptl_absorpt_empirical_full_min 0.799
####################################################################### 
# 
# 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_syy-d
_database_code_depnum_ccdc_archive 'CCDC 2491484'
loop_
_audit_author_name
_audit_author_address
'Chen R.'
;Zhejiang University
China
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2026-05-05 downloaded from the CCDC.
;
_audit_creation_date             2024-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
rdchen@zju.edu.cn
_chemical_name_common            ?
_chemical_name_systematic        Phenylpropylamine_D-LA
_chemical_formula_moiety         'C9 H14 N, C3 H5 O3'
_chemical_formula_sum            'C12 H19 N O3'
_chemical_formula_weight         225.28
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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                   5.7873(3)
_cell_length_b                   17.8836(6)
_cell_length_c                   24.8439(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2571.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3337
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      66.8470
_cell_measurement_theta_min      3.0390
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.876
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_unetI/netI     0.1092
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            22640
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.358
_diffrn_reflns_theta_min         3.045
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  81.00   0.50    2.00    --   42.80 -30.00   3.00  256
  2  ω      4.00 132.00   0.50    2.00    --   42.80  30.00 163.00  256
  3  ω     56.00 183.00   0.50    9.00    --   94.00  30.00 163.00  254
  4  ω      5.00 132.00   0.50    9.00    --   94.00 -30.00   3.00  254
  5  ω    -47.00  72.00   0.50    2.00    --   42.80 -54.00-120.00  238
  6  ω    -47.00  67.00   0.50    2.00    --   42.80 -65.00-180.00  228
  7  ω    -47.00  68.00   0.50    2.00    --   42.80 -77.00  60.00  230
  8  ω     13.00 132.00   0.50    2.00    --   42.80  43.00 -30.00  238
  9  ω     18.00 132.00   0.50    2.00    --   42.80  65.00-120.00  228
 10  ω    -47.00  67.00   0.50    2.00    --   42.80 -65.00 -30.00  228
 11  ω     69.00 183.00   0.50    9.00    --   94.00  77.00-150.00  228
 12  ω      5.00 119.00   0.50    9.00    --   94.00 -77.00-180.00  228
 13  ω      5.00 121.00   0.50    9.00    --   94.00 -82.00 120.00  232
 14  ω      5.00 123.00   0.50    9.00    --   94.00 -50.00  60.00  236
 15  ω     67.00 183.00   0.50    9.00    --   94.00  59.00   0.00  232
 16  ω      5.00 119.00   0.50    9.00    --   94.00 -77.00  30.00  228
 17  ω      5.00 123.00   0.50    9.00    --   94.00 -50.00-180.00  236
 18  ω     15.00 132.00   0.50    2.00    --   42.80  82.00 150.00  234
 19  ω     17.00 132.00   0.50    2.00    --   42.80  77.00  30.00  230
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0127853000
_diffrn_orient_matrix_UB_12      -0.0547146000
_diffrn_orient_matrix_UB_13      0.0477820000
_diffrn_orient_matrix_UB_21      0.1045083000
_diffrn_orient_matrix_UB_22      0.0621674000
_diffrn_orient_matrix_UB_23      0.0354299000
_diffrn_orient_matrix_UB_31      -0.2443854000
_diffrn_orient_matrix_UB_32      0.0237234000
_diffrn_orient_matrix_UB_33      0.0175919000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2888
_reflns_number_total             4666
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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         0.181
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 888 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      0.912
_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)+(0.0459P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1059
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22), C2(H2), C5(H5), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C17(H17), C9(H9), C10(H10), C8(H8), C20(H20), C12(H12), C19(H19),
 C18(H18), C11(H11)
2.d Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C), N1(H1A,H1B,H1C), C24(H24A,H24B,H24C), C3(H3A,H3B,H3C),
 C6(H6A,H6B,H6C), C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;
_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 0.2626(5) 0.57779(12) 0.17872(10) 0.0381(7) Uani 1 1 d . . . . .
O5 O 0.1142(5) 0.78287(11) 0.34266(10) 0.0359(7) Uani 1 1 d . . . . .
O4 O 0.2583(5) 0.89506(12) 0.32512(11) 0.0386(7) Uani 1 1 d . . . . .
O3 O 0.3473(5) 0.66842(13) 0.30258(10) 0.0378(7) Uani 1 1 d . . . . .
H3 H 0.283317 0.709083 0.310605 0.057 Uiso 1 1 calc R U . . .
O2 O -0.0096(6) 0.61724(13) 0.23490(11) 0.0381(7) Uani 1 1 d . . . . .
O6 O -0.3157(5) 0.82599(12) 0.33305(13) 0.0433(8) Uani 1 1 d . . . . .
H6 H -0.448976 0.843952 0.329618 0.065 Uiso 1 1 calc R U . . .
N2 N 0.7095(6) 0.54447(13) 0.15447(11) 0.0309(8) Uani 1 1 d . . . . .
H2A H 0.731472 0.494648 0.159873 0.037 Uiso 1 1 calc R U . . .
H2B H 0.567558 0.557846 0.166964 0.037 Uiso 1 1 calc R U . . .
H2C H 0.820186 0.570661 0.172393 0.037 Uiso 1 1 calc R U . . .
N1 N -0.1809(6) 0.66465(14) 0.33209(12) 0.0344(8) Uani 1 1 d . . . . .
H1A H -0.130723 0.655950 0.297949 0.041 Uiso 1 1 calc R U . . .
H1B H -0.117839 0.707956 0.344503 0.041 Uiso 1 1 calc R U . . .
H1C H -0.337663 0.668576 0.332174 0.041 Uiso 1 1 calc R U . . .
C4 C 0.1963(9) 0.61546(18) 0.21865(17) 0.0338(10) Uani 1 1 d . . . . .
C1 C 0.0887(8) 0.85045(18) 0.33009(15) 0.0316(10) Uani 1 1 d . . . . .
C22 C 0.7247(8) 0.56136(17) 0.09551(14) 0.0314(10) Uani 1 1 d . . . . .
H22 H 0.588894 0.537674 0.077357 0.038 Uiso 1 1 calc R U . . .
C16 C 0.7075(8) 0.64548(18) 0.08759(16) 0.0329(10) Uani 1 1 d . . . . .
C2 C -0.1487(8) 0.88110(18) 0.31889(16) 0.0340(10) Uani 1 1 d . . . . .
H2 H -0.173401 0.925980 0.342205 0.041 Uiso 1 1 calc R U . . .
C5 C 0.3776(8) 0.6644(2) 0.24557(16) 0.0381(10) Uani 1 1 d . . . . .
H5 H 0.532434 0.641621 0.238430 0.046 Uiso 1 1 calc R U . . .
C7 C -0.1258(8) 0.62255(19) 0.42668(17) 0.0378(11) Uani 1 1 d . . . . .
C13 C -0.1094(9) 0.60140(19) 0.36763(16) 0.0404(11) Uani 1 1 d . . . . .
H13 H 0.056213 0.589991 0.359638 0.048 Uiso 1 1 calc R U . . .
C21 C 0.8799(9) 0.69215(19) 0.10694(16) 0.0390(11) Uani 1 1 d . . . . .
H21 H 1.011146 0.671452 0.124397 0.047 Uiso 1 1 calc R U . . .
C23 C 0.9427(8) 0.52721(18) 0.07204(15) 0.0355(11) Uani 1 1 d . . . . .
H23A H 0.947544 0.473318 0.081065 0.043 Uiso 1 1 calc R U . . .
H23B H 1.079204 0.551325 0.088625 0.043 Uiso 1 1 calc R U . . .
C17 C 0.5204(8) 0.6767(2) 0.06114(16) 0.0400(11) Uani 1 1 d . . . . .
H17 H 0.401767 0.645321 0.047474 0.048 Uiso 1 1 calc R U . . .
C9 C -0.3310(9) 0.6762(2) 0.50220(19) 0.0501(13) Uani 1 1 d . . . . .
H9 H -0.463535 0.700741 0.516213 0.060 Uiso 1 1 calc R U . . .
C10 C -0.1507(10) 0.6568(2) 0.53614(19) 0.0495(13) Uani 1 1 d . . . . .
H10 H -0.159509 0.668475 0.573388 0.059 Uiso 1 1 calc R U . . .
C8 C -0.3178(9) 0.6595(2) 0.44734(17) 0.0425(12) Uani 1 1 d . . . . .
H8 H -0.440604 0.673419 0.424032 0.051 Uiso 1 1 calc R U . . .
C20 C 0.8608(9) 0.7692(2) 0.10082(16) 0.0467(13) Uani 1 1 d . . . . .
H20 H 0.978528 0.800905 0.114578 0.056 Uiso 1 1 calc R U . . .
C12 C 0.0554(9) 0.6038(2) 0.46128(19) 0.0484(12) Uani 1 1 d . . . . .
H12 H 0.188688 0.579508 0.447409 0.058 Uiso 1 1 calc R U . . .
C19 C 0.6739(9) 0.7998(2) 0.07512(18) 0.0482(13) Uani 1 1 d . . . . .
H19 H 0.661084 0.852552 0.071621 0.058 Uiso 1 1 calc R U . . .
C18 C 0.5049(9) 0.7541(2) 0.05441(18) 0.0477(13) Uani 1 1 d . . . . .
H18 H 0.377723 0.775136 0.035547 0.057 Uiso 1 1 calc R U . . .
C11 C 0.0424(10) 0.6205(2) 0.5160(2) 0.0560(14) Uani 1 1 d . . . . .
H11 H 0.165353 0.607076 0.539409 0.067 Uiso 1 1 calc R U . . .
C14 C -0.2523(10) 0.53243(18) 0.35209(19) 0.0575(15) Uani 1 1 d . . . . .
H14A H -0.411215 0.538342 0.366217 0.069 Uiso 1 1 calc R U . . .
H14B H -0.262239 0.529447 0.312362 0.069 Uiso 1 1 calc R U . . .
C24 C 0.9553(9) 0.5364(2) 0.01113(16) 0.0504(14) Uani 1 1 d . . . . .
H24A H 0.830079 0.507881 -0.005741 0.076 Uiso 1 1 calc R U . . .
H24B H 1.104420 0.517747 -0.001887 0.076 Uiso 1 1 calc R U . . .
H24C H 0.939490 0.589387 0.001842 0.076 Uiso 1 1 calc R U . . .
C3 C -0.1704(9) 0.9051(2) 0.26026(16) 0.0506(13) Uani 1 1 d . . . . .
H3A H -0.133481 0.862760 0.236771 0.076 Uiso 1 1 calc R U . . .
H3B H -0.062838 0.946256 0.253085 0.076 Uiso 1 1 calc R U . . .
H3C H -0.328850 0.921817 0.253232 0.076 Uiso 1 1 calc R U . . .
C6 C 0.3731(11) 0.7411(2) 0.21937(17) 0.0642(16) Uani 1 1 d . . . . .
H6A H 0.220718 0.763856 0.224600 0.096 Uiso 1 1 calc R U . . .
H6B H 0.404258 0.736087 0.180761 0.096 Uiso 1 1 calc R U . . .
H6C H 0.491563 0.772900 0.235839 0.096 Uiso 1 1 calc R U . . .
C15 C -0.1508(12) 0.4598(2) 0.3735(2) 0.088(2) Uani 1 1 d . . . . .
H15A H 0.005514 0.453085 0.359175 0.131 Uiso 1 1 calc R U . . .
H15B H -0.248187 0.417754 0.362316 0.131 Uiso 1 1 calc R U . . .
H15C H -0.144476 0.461775 0.412929 0.131 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 C4 1.259(4) . ?
O5 C1 1.257(4) . ?
O4 C1 1.271(5) . ?
O3 H3 0.8400 . ?
O3 C5 1.429(4) . ?
O2 C4 1.259(5) . ?
O6 H6 0.8400 . ?
O6 C2 1.424(5) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N2 C22 1.498(4) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C13 1.493(4) . ?
C4 C5 1.521(6) . ?
C1 C2 1.505(6) . ?
C22 H22 1.0000 . ?
C22 C16 1.520(4) . ?
C22 C23 1.518(6) . ?
C16 C21 1.387(6) . ?
C16 C17 1.384(6) . ?
C2 H2 1.0000 . ?
C2 C3 1.524(5) . ?
C5 H5 1.0000 . ?
C5 C6 1.519(6) . ?
C7 C13 1.518(6) . ?
C7 C8 1.391(6) . ?
C7 C12 1.397(6) . ?
C13 H13 1.0000 . ?
C13 C14 1.534(6) . ?
C21 H21 0.9500 . ?
C21 C20 1.391(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.524(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.397(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(7) . ?
C9 C8 1.397(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(7) . ?
C8 H8 0.9500 . ?
C20 H20 0.9500 . ?
C20 C19 1.370(6) . ?
C12 H12 0.9500 . ?
C12 C11 1.394(6) . ?
C19 H19 0.9500 . ?
C19 C18 1.374(6) . ?
C18 H18 0.9500 . ?
C11 H11 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.522(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C5 O3 H3 109.5 . . ?
C2 O6 H6 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C22 N2 H2A 109.5 . . ?
C22 N2 H2B 109.5 . . ?
C22 N2 H2C 109.5 . . ?
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 . . ?
O1 C4 C5 116.4(4) . . ?
O2 C4 O1 123.7(4) . . ?
O2 C4 C5 119.8(4) . . ?
O5 C1 O4 122.5(4) . . ?
O5 C1 C2 120.2(4) . . ?
O4 C1 C2 117.3(3) . . ?
N2 C22 H22 108.0 . . ?
N2 C22 C16 108.8(3) . . ?
N2 C22 C23 110.1(3) . . ?
C16 C22 H22 108.0 . . ?
C23 C22 H22 108.0 . . ?
C23 C22 C16 113.7(3) . . ?
C21 C16 C22 120.2(4) . . ?
C17 C16 C22 120.8(4) . . ?
C17 C16 C21 119.0(3) . . ?
O6 C2 C1 108.8(3) . . ?
O6 C2 H2 108.4 . . ?
O6 C2 C3 112.0(3) . . ?
C1 C2 H2 108.4 . . ?
C1 C2 C3 110.8(4) . . ?
C3 C2 H2 108.4 . . ?
O3 C5 C4 112.4(4) . . ?
O3 C5 H5 107.8 . . ?
O3 C5 C6 112.1(3) . . ?
C4 C5 H5 107.8 . . ?
C6 C5 C4 108.6(4) . . ?
C6 C5 H5 107.8 . . ?
C8 C7 C13 121.7(4) . . ?
C8 C7 C12 119.1(4) . . ?
C12 C7 C13 119.2(4) . . ?
N1 C13 C7 111.4(3) . . ?
N1 C13 H13 107.6 . . ?
N1 C13 C14 108.1(3) . . ?
C7 C13 H13 107.6 . . ?
C7 C13 C14 114.2(3) . . ?
C14 C13 H13 107.6 . . ?
C16 C21 H21 120.0 . . ?
C16 C21 C20 120.1(4) . . ?
C20 C21 H21 120.0 . . ?
C22 C23 H23A 109.2 . . ?
C22 C23 H23B 109.2 . . ?
C22 C23 C24 112.2(4) . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.5(4) . . ?
C18 C17 H17 119.8 . . ?
C10 C9 H9 120.0 . . ?
C10 C9 C8 119.9(5) . . ?
C8 C9 H9 120.0 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.3(4) . . ?
C11 C10 H10 119.8 . . ?
C7 C8 C9 120.3(5) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C21 C20 H20 119.7 . . ?
C19 C20 C21 120.6(4) . . ?
C19 C20 H20 119.7 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.5(5) . . ?
C11 C12 H12 119.7 . . ?
C20 C19 H19 120.0 . . ?
C20 C19 C18 119.9(3) . . ?
C18 C19 H19 120.0 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.9(4) . . ?
C19 C18 H18 120.1 . . ?
C10 C11 C12 119.7(5) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 C13 113.0(5) . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 C4 C5 O3 -144.7(3) . . . . ?
O1 C4 C5 C6 90.6(4) . . . . ?
O5 C1 C2 O6 8.7(5) . . . . ?
O5 C1 C2 C3 -114.9(4) . . . . ?
O4 C1 C2 O6 -172.8(3) . . . . ?
O4 C1 C2 C3 63.6(4) . . . . ?
O2 C4 C5 O3 38.9(5) . . . . ?
O2 C4 C5 C6 -85.8(5) . . . . ?
N2 C22 C16 C21 65.6(5) . . . . ?
N2 C22 C16 C17 -114.3(4) . . . . ?
N2 C22 C23 C24 174.6(3) . . . . ?
N1 C13 C14 C15 163.5(4) . . . . ?
C22 C16 C21 C20 -178.4(4) . . . . ?
C22 C16 C17 C18 179.5(4) . . . . ?
C16 C22 C23 C24 -63.1(4) . . . . ?
C16 C21 C20 C19 -0.8(7) . . . . ?
C16 C17 C18 C19 -1.4(7) . . . . ?
C7 C13 C14 C15 -71.9(5) . . . . ?
C7 C12 C11 C10 -0.8(7) . . . . ?
C13 C7 C8 C9 178.0(3) . . . . ?
C13 C7 C12 C11 -178.1(4) . . . . ?
C21 C16 C17 C18 -0.5(6) . . . . ?
C21 C20 C19 C18 -1.0(7) . . . . ?
C23 C22 C16 C21 -57.5(5) . . . . ?
C23 C22 C16 C17 122.6(4) . . . . ?
C17 C16 C21 C20 1.5(6) . . . . ?
C9 C10 C11 C12 0.4(7) . . . . ?
C10 C9 C8 C7 0.9(6) . . . . ?
C8 C7 C13 N1 45.6(5) . . . . ?
C8 C7 C13 C14 -77.3(4) . . . . ?
C8 C7 C12 C11 1.3(6) . . . . ?
C8 C9 C10 C11 -0.4(6) . . . . ?
C20 C19 C18 C17 2.1(7) . . . . ?
C12 C7 C13 N1 -135.1(4) . . . . ?
C12 C7 C13 C14 102.1(5) . . . . ?
C12 C7 C8 C9 -1.3(6) . . . . ?


_olex2_submission_original_sample_id D
_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 4.603
_oxdiff_exptl_absorpt_empirical_full_min 0.775
####################################################################### 
# 
# 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_0702d_auto
_database_code_depnum_ccdc_archive 'CCDC 2491489'
loop_
_audit_author_name
_audit_author_address
'Chen R.'
;Zhejiang University
China
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2026-05-05 downloaded from the CCDC.
;
_audit_creation_date             2024-07-02
_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        Phenylethylamine_D-LA
_chemical_formula_moiety         'C8 H12 N, C3 H5 O3'
_chemical_formula_sum            'C11 H17 N O3'
_chemical_formula_weight         211.25
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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                   6.27222(5)
_cell_length_b                   8.07833(6)
_cell_length_c                   22.6180(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1146.033(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8661
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      67.6740
_cell_measurement_theta_min      1.9570
_shelx_estimated_absorpt_T_max   0.868
_shelx_estimated_absorpt_T_min   0.760
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11393
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.976
_diffrn_reflns_theta_min         3.909
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00  66.00   0.50    0.50    --   42.50 -68.00  58.00  224
  2  ω    -46.00  71.00   0.50    0.50    --   42.50 -52.00-127.00  234
  3  ω     14.00 131.00   0.50    0.50    --   42.50  52.00  18.00  234
  4  ω     65.00 183.00   0.50    0.50    --   94.00  52.00  18.00  236
  5  ω      5.00 118.00   0.50    0.50    --   94.00 -68.00  58.00  226
  6  ω     70.00 183.00   0.50    0.50    --   94.00  68.00-168.00  226
  7  ω      5.00 123.00   0.50    0.50    --   94.00 -52.00-127.00  236
  8  ω     19.00 131.00   0.50    0.50    --   42.50  65.00 -90.00  224
  9  ω    -46.00  71.00   0.50    0.50    --   42.50 -54.00 120.00  234
 10  ω     19.00 131.00   0.50    0.50    --   42.50  68.00-168.00  224
 11  ω    -46.00  69.00   0.50    0.50    --   42.50 -82.00   0.00  230
 12  ω     19.00 131.00   0.50    0.50    --   42.50  65.00-120.00  224
 13  ω     70.00 183.00   0.50    0.50    --   94.00  68.00 -60.00  226
 14  ω      5.00 123.00   0.50    0.50    --   94.00 -50.00 120.00  236
 15  ω     60.00 183.00   0.50    0.50    --   94.00  33.00 120.00  246
 16  ω      5.00 118.00   0.50    0.50    --   94.00 -68.00 120.00  226
 17  ω     60.00 183.00   0.50    0.50    --   94.00  33.00   0.00  246
 18  ω      5.00 118.00   0.50    0.50    --   94.00 -68.00 -60.00  226
 19  ω     67.00 183.00   0.50    0.50    --   94.00  59.00-120.00  232
 20  ω     16.00 131.00   0.50    0.50    --   42.50  82.00 120.00  230
 21  ω     16.00 105.00   0.50    0.50    --   42.50  82.00 -60.00  178
 22  ω     19.00 131.00   0.50    0.50    --   42.50  65.00  60.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1086969000
_diffrn_orient_matrix_UB_12      -0.1559162000
_diffrn_orient_matrix_UB_13      -0.0250669000
_diffrn_orient_matrix_UB_21      0.1558428000
_diffrn_orient_matrix_UB_22      -0.1097853000
_diffrn_orient_matrix_UB_23      0.0351232000
_diffrn_orient_matrix_UB_31      -0.1557332000
_diffrn_orient_matrix_UB_32      -0.0009932000
_diffrn_orient_matrix_UB_33      0.0526849000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2040
_reflns_number_total             2091
_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 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_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         -0.097
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 808 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.18(6)
_refine_ls_extinction_coef       0.0086(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   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2091
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0260
_refine_ls_restrained_S_all      1.070
_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)+(0.0275P)²+0.1930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0640
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C10(H10), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C8(H8A,H8B,H8C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_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 0.80847(16) 0.30254(14) 0.21549(5) 0.0287(3) Uani 1 1 d . . . . .
O3 O 0.28028(18) 0.42328(15) 0.19659(5) 0.0305(3) Uani 1 1 d . . . . .
H3A H 0.314378 0.511401 0.213892 0.046 Uiso 1 1 calc R U . . .
O2 O 0.52824(19) 0.20262(16) 0.26376(5) 0.0356(3) Uani 1 1 d . . . . .
C9 C 0.6116(2) 0.28029(19) 0.22156(7) 0.0229(3) Uani 1 1 d . . . . .
N1 N 1.0995(2) 0.15783(15) 0.29196(5) 0.0221(3) Uani 1 1 d . . . . .
H1A H 1.235340 0.182190 0.280784 0.033 Uiso 1 1 calc R U . . .
H1B H 1.006934 0.194515 0.263892 0.033 Uiso 1 1 calc R U . . .
H1C H 1.085527 0.046327 0.296145 0.033 Uiso 1 1 calc R U . . .
C10 C 0.4655(3) 0.34748(19) 0.17289(7) 0.0244(3) Uani 1 1 d . . . . .
H10 H 0.545794 0.430708 0.148895 0.029 Uiso 1 1 calc R U . . .
C1 C 1.1803(3) 0.1620(2) 0.39882(7) 0.0252(4) Uani 1 1 d . . . . .
C7 C 1.0514(3) 0.2410(2) 0.34972(7) 0.0283(4) Uani 1 1 d . . . . .
H7 H 0.896774 0.224546 0.358713 0.034 Uiso 1 1 calc R U . . .
C2 C 1.3782(3) 0.2214(2) 0.41557(8) 0.0332(4) Uani 1 1 d . . . . .
H2 H 1.436518 0.315787 0.396397 0.040 Uiso 1 1 calc R U . . .
C6 C 1.0989(4) 0.0239(2) 0.42747(8) 0.0383(5) Uani 1 1 d . . . . .
H6 H 0.963380 -0.018437 0.416395 0.046 Uiso 1 1 calc R U . . .
C3 C 1.4921(4) 0.1435(3) 0.46039(9) 0.0488(5) Uani 1 1 d . . . . .
H3 H 1.627735 0.184978 0.471832 0.059 Uiso 1 1 calc R U . . .
C11 C 0.3963(3) 0.2066(2) 0.13311(8) 0.0404(5) Uani 1 1 d . . . . .
H11A H 0.326011 0.121083 0.156850 0.061 Uiso 1 1 calc R U . . .
H11B H 0.521505 0.159217 0.113471 0.061 Uiso 1 1 calc R U . . .
H11C H 0.296678 0.248410 0.103259 0.061 Uiso 1 1 calc R U . . .
C4 C 1.4092(5) 0.0069(3) 0.48813(9) 0.0584(7) Uani 1 1 d . . . . .
H4 H 1.487593 -0.046533 0.518573 0.070 Uiso 1 1 calc R U . . .
C8 C 1.0909(4) 0.4257(2) 0.34154(9) 0.0478(6) Uani 1 1 d . . . . .
H8A H 1.238829 0.443574 0.329117 0.072 Uiso 1 1 calc R U . . .
H8B H 1.065234 0.483293 0.378992 0.072 Uiso 1 1 calc R U . . .
H8C H 0.994133 0.468914 0.311235 0.072 Uiso 1 1 calc R U . . .
C5 C 1.2129(5) -0.0524(3) 0.47184(9) 0.0562(6) Uani 1 1 d . . . . .
H5 H 1.155243 -0.146584 0.491256 0.067 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 C9 1.2554(19) . ?
O3 H3A 0.8400 . ?
O3 C10 1.419(2) . ?
O2 C9 1.2563(19) . ?
C9 C10 1.532(2) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C7 1.4999(19) . ?
C10 H10 1.0000 . ?
C10 C11 1.514(2) . ?
C1 C7 1.515(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.388(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.523(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.378(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.372(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C5 1.371(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C5 H5 0.9500 . ?

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
C10 O3 H3A 109.5 . . ?
O1 C9 O2 124.33(15) . . ?
O1 C9 C10 117.32(14) . . ?
O2 C9 C10 118.31(13) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C7 N1 H1A 109.5 . . ?
C7 N1 H1B 109.5 . . ?
C7 N1 H1C 109.5 . . ?
O3 C10 C9 111.79(12) . . ?
O3 C10 H10 109.1 . . ?
O3 C10 C11 108.31(14) . . ?
C9 C10 H10 109.1 . . ?
C11 C10 C9 109.40(13) . . ?
C11 C10 H10 109.1 . . ?
C2 C1 C7 122.24(16) . . ?
C2 C1 C6 118.76(17) . . ?
C6 C1 C7 118.99(16) . . ?
N1 C7 C1 110.03(12) . . ?
N1 C7 H7 108.2 . . ?
N1 C7 C8 107.46(13) . . ?
C1 C7 H7 108.2 . . ?
C1 C7 C8 114.51(15) . . ?
C8 C7 H7 108.2 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.22(19) . . ?
C3 C2 H2 119.9 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.8 . . ?

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 C9 C10 O3 -138.18(15) . . . . ?
O1 C9 C10 C11 101.85(17) . . . . ?
O2 C9 C10 O3 43.96(19) . . . . ?
O2 C9 C10 C11 -76.02(19) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C1 C6 C5 C4 -0.3(3) . . . . ?
C7 C1 C2 C3 -179.13(16) . . . . ?
C7 C1 C6 C5 179.20(18) . . . . ?
C2 C1 C7 N1 92.21(17) . . . . ?
C2 C1 C7 C8 -28.9(2) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C6 C1 C7 N1 -86.83(18) . . . . ?
C6 C1 C7 C8 152.02(17) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?


_olex2_submission_original_sample_id D
_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 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.863
