# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_1_pl_tw
_database_code_depnum_ccdc_archive 'CCDC 2384777'
loop_
_audit_author_name
_audit_author_address
yunfeng
;Southwest Forestry University
China
;
_audit_update_record             
;
2024-09-18 deposited with the CCDC.	2026-01-16 downloaded from the CCDC.
;
_audit_creation_date             2021-06-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 N O4'
_chemical_formula_sum            'C19 H17 N O4'
_chemical_formula_weight         323.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.110(5)
_cell_length_b                   8.813(6)
_cell_length_c                   12.868(9)
_cell_angle_alpha                83.048(13)
_cell_angle_beta                 75.01(4)
_cell_angle_gamma                86.742(13)
_cell_volume                     772.9(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1603
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.916
_cell_measurement_theta_min      2.967
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0859 before and 0.0472 after correction.
The Ratio of minimum to maximum transmission is 0.8163.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2692
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.329
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1734
_reflns_number_total             2692
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0775
_refine_ls_restrained_S_all      1.117
_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)+(0.1091P)²+0.0514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2028
_refine_ls_wR_factor_ref         0.2221
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.637(6)
 0.363(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
3.a Ternary CH refined with riding coordinates:
 C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C4(H4A), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C18(H18)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2220(4) -0.1242(3) 0.4863(2) 0.0432(8) Uani 1 1 d . . . . .
O2 O 0.7502(4) 0.5838(3) 0.3030(3) 0.0455(8) Uani 1 1 d . . . . .
H2 H 0.825962 0.510926 0.307126 0.068 Uiso 1 1 calc R U . . .
O3 O 0.2819(4) 0.4926(3) 0.4231(2) 0.0412(8) Uani 1 1 d . . . . .
O4 O 0.0678(4) -0.3055(3) 0.6457(2) 0.0435(8) Uani 1 1 d . . . . .
H4 H 0.113543 -0.274925 0.581850 0.065 Uiso 1 1 calc R U . . .
N1 N 0.4418(5) 0.2828(3) 0.3298(2) 0.0320(8) Uani 1 1 d . . . . .
C1 C 0.6403(6) 0.2425(6) 0.0387(3) 0.0474(12) Uani 1 1 d . . . . .
H1 H 0.651347 0.174929 -0.012905 0.057 Uiso 1 1 calc R U . . .
C2 C 0.0037(7) 0.0451(5) 0.8360(3) 0.0483(12) Uani 1 1 d . . . . .
H2A H -0.009539 0.123082 0.880234 0.058 Uiso 1 1 calc R U . . .
C3 C 0.1178(5) -0.0423(4) 0.6603(3) 0.0302(9) Uani 1 1 d . . . . .
C4 C 0.3629(5) 0.1531(4) 0.3879(3) 0.0308(9) Uani 1 1 d . . . . .
H4A H 0.364899 0.069738 0.349673 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4612(6) 0.4213(4) 0.3794(3) 0.0315(9) Uani 1 1 d . . . . .
H5 H 0.533277 0.397042 0.435001 0.038 Uiso 1 1 calc R U . . .
C6 C 0.5307(5) 0.3008(4) 0.2187(3) 0.0311(9) Uani 1 1 d . . . . .
C7 C 0.7236(7) 0.3833(6) 0.0078(4) 0.0547(13) Uani 1 1 d . . . . .
H7 H 0.788486 0.410047 -0.064159 0.066 Uiso 1 1 calc R U . . .
C8 C 0.0472(5) -0.1873(4) 0.7060(3) 0.0327(9) Uani 1 1 d . . . . .
C9 C -0.0670(7) -0.0969(6) 0.8790(4) 0.0533(13) Uani 1 1 d . . . . .
H9 H -0.131080 -0.114588 0.951930 0.064 Uiso 1 1 calc R U . . .
C10 C 0.2092(5) -0.0154(4) 0.5428(3) 0.0313(9) Uani 1 1 d . . . . .
C11 C -0.0430(6) -0.2119(5) 0.8141(4) 0.0466(12) Uani 1 1 d . . . . .
H11 H -0.088682 -0.308548 0.843887 0.056 Uiso 1 1 calc R U . . .
C12 C 0.7118(6) 0.4858(5) 0.0831(3) 0.0471(12) Uani 1 1 d . . . . .
H12 H 0.768441 0.580924 0.062505 0.056 Uiso 1 1 calc R U . . .
C13 C 0.2826(5) 0.1322(4) 0.4940(3) 0.0322(9) Uani 1 1 d . . . . .
H13 H 0.273979 0.212228 0.536094 0.039 Uiso 1 1 calc R U . . .
C14 C 0.0940(6) 0.0722(5) 0.7278(3) 0.0390(10) Uani 1 1 d . . . . .
H14 H 0.140029 0.169095 0.699306 0.047 Uiso 1 1 calc R U . . .
C15 C 0.2409(6) 0.5994(5) 0.3380(3) 0.0432(11) Uani 1 1 d . . . . .
H15A H 0.146254 0.677083 0.367055 0.052 Uiso 1 1 calc R U . . .
H15B H 0.191463 0.547890 0.288384 0.052 Uiso 1 1 calc R U . . .
C16 C 0.4345(6) 0.6684(5) 0.2824(4) 0.0441(11) Uani 1 1 d . . . . .
H16A H 0.462507 0.748730 0.321089 0.053 Uiso 1 1 calc R U . . .
H16B H 0.438644 0.709916 0.208519 0.053 Uiso 1 1 calc R U . . .
C17 C 0.5774(6) 0.5324(4) 0.2854(3) 0.0326(9) Uani 1 1 d . . . . .
C18 C 0.5414(6) 0.1992(5) 0.1435(3) 0.0410(11) Uani 1 1 d . . . . .
H18 H 0.483413 0.104515 0.163460 0.049 Uiso 1 1 calc R U . . .
C19 C 0.6141(6) 0.4434(4) 0.1893(3) 0.0334(10) 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
O1 C10 1.258(5) . ?
O2 H2 0.8200 . ?
O2 C17 1.413(5) . ?
O3 C5 1.400(4) . ?
O3 C15 1.433(5) . ?
O4 H4 0.8200 . ?
O4 C8 1.351(5) . ?
N1 C4 1.352(5) . ?
N1 C5 1.473(5) . ?
N1 C6 1.399(5) . ?
C1 H1 0.9300 . ?
C1 C7 1.376(7) . ?
C1 C18 1.369(6) . ?
C2 H2A 0.9300 . ?
C2 C9 1.373(6) . ?
C2 C14 1.371(6) . ?
C3 C8 1.403(5) . ?
C3 C10 1.480(5) . ?
C3 C14 1.385(5) . ?
C4 H4A 0.9300 . ?
C4 C13 1.331(5) . ?
C5 H5 0.9800 . ?
C5 C17 1.547(5) . ?
C6 C18 1.381(5) . ?
C6 C19 1.388(6) . ?
C7 H7 0.9300 . ?
C7 C12 1.386(6) . ?
C8 C11 1.370(6) . ?
C9 H9 0.9300 . ?
C9 C11 1.366(6) . ?
C10 C13 1.439(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C19 1.380(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.502(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.530(5) . ?
C17 C19 1.502(6) . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O2 H2 109.5 . . ?
C5 O3 C15 106.5(3) . . ?
C8 O4 H4 109.5 . . ?
C4 N1 C5 123.1(3) . . ?
C4 N1 C6 125.9(3) . . ?
C6 N1 C5 110.8(3) . . ?
C7 C1 H1 119.2 . . ?
C18 C1 H1 119.2 . . ?
C18 C1 C7 121.6(4) . . ?
C9 C2 H2A 120.0 . . ?
C14 C2 H2A 120.0 . . ?
C14 C2 C9 120.1(4) . . ?
C8 C3 C10 119.6(4) . . ?
C14 C3 C8 118.0(4) . . ?
C14 C3 C10 122.4(4) . . ?
N1 C4 H4A 116.6 . . ?
C13 C4 N1 126.9(4) . . ?
C13 C4 H4A 116.6 . . ?
O3 C5 N1 113.1(3) . . ?
O3 C5 H5 110.2 . . ?
O3 C5 C17 107.9(3) . . ?
N1 C5 H5 110.2 . . ?
N1 C5 C17 105.1(3) . . ?
C17 C5 H5 110.2 . . ?
C18 C6 N1 128.7(4) . . ?
C18 C6 C19 121.5(4) . . ?
C19 C6 N1 109.8(3) . . ?
C1 C7 H7 119.7 . . ?
C1 C7 C12 120.6(4) . . ?
C12 C7 H7 119.7 . . ?
O4 C8 C3 121.5(4) . . ?
O4 C8 C11 118.5(4) . . ?
C11 C8 C3 120.0(4) . . ?
C2 C9 H9 120.1 . . ?
C11 C9 C2 119.7(4) . . ?
C11 C9 H9 120.1 . . ?
O1 C10 C3 118.7(3) . . ?
O1 C10 C13 120.5(4) . . ?
C13 C10 C3 120.7(4) . . ?
C8 C11 H11 119.5 . . ?
C9 C11 C8 121.0(4) . . ?
C9 C11 H11 119.5 . . ?
C7 C12 H12 120.7 . . ?
C19 C12 C7 118.5(4) . . ?
C19 C12 H12 120.7 . . ?
C4 C13 C10 119.3(4) . . ?
C4 C13 H13 120.4 . . ?
C10 C13 H13 120.4 . . ?
C2 C14 C3 121.1(4) . . ?
C2 C14 H14 119.4 . . ?
C3 C14 H14 119.4 . . ?
O3 C15 H15A 111.0 . . ?
O3 C15 H15B 111.0 . . ?
O3 C15 C16 104.0(3) . . ?
H15A C15 H15B 109.0 . . ?
C16 C15 H15A 111.0 . . ?
C16 C15 H15B 111.0 . . ?
C15 C16 H16A 111.2 . . ?
C15 C16 H16B 111.2 . . ?
C15 C16 C17 103.0(3) . . ?
H16A C16 H16B 109.1 . . ?
C17 C16 H16A 111.2 . . ?
C17 C16 H16B 111.2 . . ?
O2 C17 C5 114.2(3) . . ?
O2 C17 C16 108.8(3) . . ?
O2 C17 C19 113.0(3) . . ?
C16 C17 C5 102.5(3) . . ?
C19 C17 C5 103.5(3) . . ?
C19 C17 C16 114.4(3) . . ?
C1 C18 C6 117.8(4) . . ?
C1 C18 H18 121.1 . . ?
C6 C18 H18 121.1 . . ?
C6 C19 C17 110.8(3) . . ?
C12 C19 C6 120.0(4) . . ?
C12 C19 C17 129.3(4) . . ?

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 C10 C13 C4 0.6(6) . . . . ?
O2 C17 C19 C6 125.1(3) . . . . ?
O2 C17 C19 C12 -55.9(5) . . . . ?
O3 C5 C17 O2 115.6(3) . . . . ?
O3 C5 C17 C16 -1.9(4) . . . . ?
O3 C5 C17 C19 -121.1(3) . . . . ?
O3 C15 C16 C17 37.8(4) . . . . ?
O4 C8 C11 C9 179.7(4) . . . . ?
N1 C4 C13 C10 -178.6(3) . . . . ?
N1 C5 C17 O2 -123.5(3) . . . . ?
N1 C5 C17 C16 119.0(3) . . . . ?
N1 C5 C17 C19 -0.2(4) . . . . ?
N1 C6 C18 C1 -178.9(4) . . . . ?
N1 C6 C19 C12 179.4(3) . . . . ?
N1 C6 C19 C17 -1.4(4) . . . . ?
C1 C7 C12 C19 -0.2(7) . . . . ?
C2 C9 C11 C8 -1.4(7) . . . . ?
C3 C8 C11 C9 0.4(6) . . . . ?
C3 C10 C13 C4 -179.6(3) . . . . ?
C4 N1 C5 O3 -68.5(4) . . . . ?
C4 N1 C5 C17 174.1(3) . . . . ?
C4 N1 C6 C18 6.7(6) . . . . ?
C4 N1 C6 C19 -173.3(3) . . . . ?
C5 O3 C15 C16 -40.4(4) . . . . ?
C5 N1 C4 C13 4.1(6) . . . . ?
C5 N1 C6 C18 -178.7(4) . . . . ?
C5 N1 C6 C19 1.2(4) . . . . ?
C5 C17 C19 C6 1.0(4) . . . . ?
C5 C17 C19 C12 -180.0(4) . . . . ?
C6 N1 C4 C13 178.0(4) . . . . ?
C6 N1 C5 O3 116.8(3) . . . . ?
C6 N1 C5 C17 -0.6(4) . . . . ?
C7 C1 C18 C6 -1.2(6) . . . . ?
C7 C12 C19 C6 0.1(6) . . . . ?
C7 C12 C19 C17 -178.9(4) . . . . ?
C8 C3 C10 O1 -0.2(5) . . . . ?
C8 C3 C10 C13 179.9(3) . . . . ?
C8 C3 C14 C2 -0.2(6) . . . . ?
C9 C2 C14 C3 -0.8(7) . . . . ?
C10 C3 C8 O4 2.8(5) . . . . ?
C10 C3 C8 C11 -178.0(3) . . . . ?
C10 C3 C14 C2 178.1(4) . . . . ?
C14 C2 C9 C11 1.6(7) . . . . ?
C14 C3 C8 O4 -178.9(3) . . . . ?
C14 C3 C8 C11 0.4(6) . . . . ?
C14 C3 C10 O1 -178.5(4) . . . . ?
C14 C3 C10 C13 1.7(6) . . . . ?
C15 O3 C5 N1 -89.6(4) . . . . ?
C15 O3 C5 C17 26.1(4) . . . . ?
C15 C16 C17 O2 -142.8(3) . . . . ?
C15 C16 C17 C5 -21.5(4) . . . . ?
C15 C16 C17 C19 89.8(4) . . . . ?
C16 C17 C19 C6 -109.7(4) . . . . ?
C16 C17 C19 C12 69.4(5) . . . . ?
C18 C1 C7 C12 0.8(7) . . . . ?
C18 C6 C19 C12 -0.6(6) . . . . ?
C18 C6 C19 C17 178.6(3) . . . . ?
C19 C6 C18 C1 1.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.637(6)
2 0.363(6)

