# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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 
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data_131202b_0m
_database_code_depnum_ccdc_archive 'CCDC 2375967'
loop_
_audit_author_name
_audit_author_address
'He Xinwei'
;Anhui Normal University
China
;
_audit_update_record             
;
2024-08-19 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_audit_creation_date             2024-05-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 N O4'
_chemical_formula_sum            'C18 H17 N O4'
_chemical_formula_weight         311.32
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.440(2)
_cell_length_b                   7.9493(7)
_cell_length_c                   15.9676(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.7360(10)
_cell_angle_gamma                90
_cell_volume                     3196.5(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6529
_cell_measurement_temperature    293.15(10)
_cell_measurement_theta_max      27.575
_cell_measurement_theta_min      2.394
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0911 before and 0.0370 after correction.
The Ratio of minimum to maximum transmission is 0.8770.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13429
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.642
_diffrn_reflns_theta_min         1.617
_diffrn_ambient_temperature      293.15(10)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2959
_reflns_number_total             3708
_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       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection       'Bruker SMART APEX II diffractometer'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.052
_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)+(0.0752P)²+1.2970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1464
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 C18(H18A,H18B,H18C)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C13(H13), C14(H14), C16(H16), C17(H17)
2.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
C1 C 0.40982(5) 0.35838(18) 0.06506(9) 0.0442(3) Uani 1 1 d . . . . .
H1 H 0.433838 0.451675 0.063937 0.053 Uiso 1 1 calc R U . . .
C2 C 0.44003(6) 0.19013(18) 0.07814(9) 0.0446(3) Uani 1 1 d . . . . .
H2 H 0.430606 0.125349 0.023327 0.054 Uiso 1 1 calc R U . . .
C3 C 0.41923(5) 0.10588(18) 0.14547(9) 0.0426(3) Uani 1 1 d . . . . .
C4 C 0.42668(6) -0.05515(19) 0.17976(9) 0.0485(3) Uani 1 1 d . . . . .
H4 H 0.446384 -0.132921 0.159245 0.058 Uiso 1 1 calc R U . . .
C5 C 0.40441(6) -0.1002(2) 0.24542(10) 0.0532(4) Uani 1 1 d . . . . .
C6 C 0.37568(6) 0.0195(2) 0.27487(10) 0.0561(4) Uani 1 1 d . . . . .
H6 H 0.360883 -0.010416 0.318659 0.067 Uiso 1 1 calc R U . . .
C7 C 0.36808(6) 0.1817(2) 0.24178(10) 0.0530(4) Uani 1 1 d . . . . .
H7 H 0.348751 0.260426 0.262483 0.064 Uiso 1 1 calc R U . . .
C8 C 0.39048(5) 0.22131(18) 0.17677(9) 0.0442(3) Uani 1 1 d . . . . .
C9 C 0.50015(6) 0.2081(2) 0.11616(10) 0.0545(4) Uani 1 1 d . . . . .
H9A H 0.508383 0.276520 0.168902 0.065 Uiso 1 1 calc R U . . .
H9B H 0.515756 0.097844 0.132602 0.065 Uiso 1 1 calc R U . . .
C10 C 0.41254(10) -0.2761(2) 0.28306(14) 0.0780(6) Uani 1 1 d . . . . .
H10A H 0.432110 -0.270877 0.344459 0.117 Uiso 1 1 calc R U . . .
H10B H 0.432027 -0.341431 0.252737 0.117 Uiso 1 1 calc R U . . .
H10C H 0.378655 -0.327696 0.275884 0.117 Uiso 1 1 calc R U . . .
C11 C 0.36152(6) 0.36059(19) -0.01815(9) 0.0470(3) Uani 1 1 d . . . . .
C12 C 0.33128(5) 0.51876(19) -0.04309(9) 0.0462(3) Uani 1 1 d . . . . .
C13 C 0.28446(7) 0.5164(2) -0.11341(11) 0.0634(4) Uani 1 1 d . . . . .
H13 H 0.272474 0.415908 -0.142476 0.076 Uiso 1 1 calc R U . . .
C14 C 0.25593(7) 0.6618(3) -0.13999(12) 0.0695(5) Uani 1 1 d . . . . .
H14 H 0.224777 0.657683 -0.186915 0.083 Uiso 1 1 calc R U . . .
C15 C 0.27228(6) 0.8137(2) -0.09890(11) 0.0565(4) Uani 1 1 d . . . . .
C16 C 0.31871(7) 0.8151(2) -0.02893(12) 0.0600(4) Uani 1 1 d . . . . .
H16 H 0.330624 0.915890 -0.000054 0.072 Uiso 1 1 calc R U . . .
C17 C 0.34758(6) 0.6702(2) -0.00128(11) 0.0548(4) Uani 1 1 d . . . . .
H17 H 0.378462 0.674492 0.046170 0.066 Uiso 1 1 calc R U . . .
C18 C 0.24085(8) 0.9720(3) -0.12862(15) 0.0767(5) Uani 1 1 d . . . . .
H18A H 0.248703 1.051112 -0.080982 0.115 Uiso 1 1 d R U . . .
H18B H 0.203623 0.946072 -0.146722 0.115 Uiso 1 1 d R U . . .
H18C H 0.250163 1.019772 -0.177152 0.115 Uiso 1 1 d R U . . .
N1 N 0.52405(5) 0.28642(18) 0.05247(9) 0.0559(3) Uani 1 1 d . . . . .
O1 O 0.38852(4) 0.37745(13) 0.13857(6) 0.0518(3) Uani 1 1 d . . . . .
O2 O 0.34869(5) 0.23254(16) -0.06032(8) 0.0719(4) Uani 1 1 d . . . . .
O3 O 0.52002(7) 0.2139(2) -0.01560(10) 0.0873(5) Uani 1 1 d . . . . .
O4 O 0.54576(7) 0.42153(19) 0.07135(11) 0.0883(5) 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
C1 H1 0.9800 . ?
C1 C2 1.5391(19) . ?
C1 C11 1.537(2) . ?
C1 O1 1.4563(16) . ?
C2 H2 0.9800 . ?
C2 C3 1.5057(18) . ?
C2 C9 1.526(2) . ?
C3 C4 1.383(2) . ?
C3 C8 1.3787(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(2) . ?
C5 C6 1.386(2) . ?
C5 C10 1.511(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(2) . ?
C8 O1 1.3770(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 N1 1.4875(19) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.478(2) . ?
C11 O2 1.2105(19) . ?
C12 C13 1.395(2) . ?
C12 C17 1.380(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(3) . ?
C15 C16 1.385(2) . ?
C15 C18 1.503(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(2) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9599 . ?
C18 H18C 0.9601 . ?
N1 O3 1.206(2) . ?
N1 O4 1.2120(19) . ?

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 C1 H1 110.4 . . ?
C11 C1 H1 110.4 . . ?
C11 C1 C2 112.79(12) . . ?
O1 C1 H1 110.4 . . ?
O1 C1 C2 107.05(10) . . ?
O1 C1 C11 105.78(11) . . ?
C1 C2 H2 110.8 . . ?
C3 C2 C1 101.31(11) . . ?
C3 C2 H2 110.8 . . ?
C3 C2 C9 108.68(11) . . ?
C9 C2 C1 114.04(12) . . ?
C9 C2 H2 110.8 . . ?
C4 C3 C2 130.96(13) . . ?
C8 C3 C2 108.93(12) . . ?
C8 C3 C4 120.03(13) . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.53(14) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C10 119.62(16) . . ?
C6 C5 C4 118.61(14) . . ?
C6 C5 C10 121.77(15) . . ?
C5 C6 H6 118.6 . . ?
C7 C6 C5 122.72(14) . . ?
C7 C6 H6 118.6 . . ?
C6 C7 H7 121.5 . . ?
C8 C7 C6 117.01(14) . . ?
C8 C7 H7 121.5 . . ?
C3 C8 C7 122.11(14) . . ?
O1 C8 C3 112.94(12) . . ?
O1 C8 C7 124.91(13) . . ?
C2 C9 H9A 109.2 . . ?
C2 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N1 C9 C2 112.03(12) . . ?
N1 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C1 118.77(12) . . ?
O2 C11 C1 119.30(13) . . ?
O2 C11 C12 121.91(13) . . ?
C13 C12 C11 118.69(14) . . ?
C17 C12 C11 123.23(13) . . ?
C17 C12 C13 118.07(14) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.41(16) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.73(15) . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C16 117.61(15) . . ?
C14 C15 C18 121.30(16) . . ?
C16 C15 C18 121.09(17) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.30(16) . . ?
C17 C16 H16 119.4 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.88(14) . . ?
C16 C17 H17 119.6 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 N1 C9 118.46(15) . . ?
O3 N1 O4 123.57(15) . . ?
O4 N1 C9 117.96(15) . . ?
C8 O1 C1 106.96(10) . . ?

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
C1 C2 C3 C4 173.20(14) . . . . ?
C1 C2 C3 C8 -10.02(14) . . . . ?
C1 C2 C9 N1 -69.35(17) . . . . ?
C1 C11 C12 C13 -173.66(14) . . . . ?
C1 C11 C12 C17 7.6(2) . . . . ?
C2 C1 C11 C12 -175.06(11) . . . . ?
C2 C1 C11 O2 6.41(19) . . . . ?
C2 C1 O1 C8 -16.48(14) . . . . ?
C2 C3 C4 C5 177.19(14) . . . . ?
C2 C3 C8 C7 -177.63(13) . . . . ?
C2 C3 C8 O1 0.30(16) . . . . ?
C2 C9 N1 O3 -62.4(2) . . . . ?
C2 C9 N1 O4 116.34(17) . . . . ?
C3 C2 C9 N1 178.47(13) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C3 C4 C5 C10 -179.94(15) . . . . ?
C3 C8 O1 C1 10.39(16) . . . . ?
C4 C3 C8 C7 -0.4(2) . . . . ?
C4 C3 C8 O1 177.49(12) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C8 0.2(2) . . . . ?
C6 C7 C8 C3 0.0(2) . . . . ?
C6 C7 C8 O1 -177.67(13) . . . . ?
C7 C8 O1 C1 -171.75(14) . . . . ?
C8 C3 C4 C5 0.7(2) . . . . ?
C9 C2 C3 C4 -66.4(2) . . . . ?
C9 C2 C3 C8 110.39(14) . . . . ?
C10 C5 C6 C7 179.49(16) . . . . ?
C11 C1 C2 C3 -100.08(13) . . . . ?
C11 C1 C2 C9 143.37(12) . . . . ?
C11 C1 O1 C8 104.03(12) . . . . ?
C11 C12 C13 C14 -178.36(16) . . . . ?
C11 C12 C17 C16 177.98(15) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C12 C17 C16 -0.7(2) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C13 C14 C15 C18 179.87(18) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C12 0.5(3) . . . . ?
C17 C12 C13 C14 0.4(3) . . . . ?
C18 C15 C16 C17 179.81(16) . . . . ?
O1 C1 C2 C3 15.85(13) . . . . ?
O1 C1 C2 C9 -100.69(13) . . . . ?
O1 C1 C11 C12 68.25(15) . . . . ?
O1 C1 C11 O2 -110.29(15) . . . . ?
O2 C11 C12 C13 4.8(2) . . . . ?
O2 C11 C12 C17 -173.86(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
