# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_zyb_0m
_database_code_depnum_ccdc_archive 'CCDC 2530693'
loop_
_audit_author_name
_audit_author_address
'Chaorong Qi'
;South China University of Technology
China
;
_audit_update_record             
;
2026-02-12 deposited with the CCDC.	2026-03-26 downloaded from the CCDC.
;
_audit_creation_date             2025-09-02
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C20 H19 N O4'
_chemical_formula_weight         337.36
_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                   7.2775(4)
_cell_length_b                   9.3509(6)
_cell_length_c                   13.7128(8)
_cell_angle_alpha                75.036(2)
_cell_angle_beta                 75.370(2)
_cell_angle_gamma                75.268(2)
_cell_volume                     854.27(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3305
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.213
_cell_measurement_theta_min      2.302
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.3308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1682 before and 0.0871 after correction.
The Ratio of minimum to maximum transmission is 0.4438.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9126
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_min         2.302
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                2567
_reflns_number_total             3459
_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 V8.41 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.064
_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     227
_refine_ls_number_reflns         3459
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0675
_refine_ls_restrained_S_all      1.066
_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)+(0.0855P)²+0.5817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1694
_refine_ls_wR_factor_ref         0.1916
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C7, C8
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C8 \\sim C7: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
within 2A
Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C10(H10A,H10B), C19(H19A,H19B)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C12(H12), C2(H2), C16(H16), C15(H15), C6(H6), C9(H9),
 C7(H7), C8(H8)
4.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
O4 O 0.7810(2) 0.89606(17) 0.03831(13) 0.0299(4) Uani 1 1 d . . . . .
O1 O 0.2919(2) -0.01919(18) 0.36746(14) 0.0315(4) Uani 1 1 d . . . . .
O3 O 0.8535(3) 0.7483(2) -0.07633(14) 0.0388(5) Uani 1 1 d . . . . .
O2 O 0.0163(3) 0.3211(2) 0.52071(15) 0.0434(5) Uani 1 1 d . . . . .
N1 N 0.0962(3) 0.5153(2) 0.30557(16) 0.0285(5) Uani 1 1 d . . . . .
H1 H 0.019235 0.583313 0.339453 0.034 Uiso 1 1 calc R U . . .
C13 C 0.5771(4) 0.4945(2) 0.12966(18) 0.0268(5) Uani 1 1 d . . . . .
H13 H 0.653035 0.443042 0.076926 0.032 Uiso 1 1 calc R U . . .
C11 C 0.2799(3) 0.5376(2) 0.25575(18) 0.0240(5) Uani 1 1 d . . . . .
C14 C 0.6521(3) 0.5981(2) 0.15668(18) 0.0254(5) Uani 1 1 d . . . . .
C18 C 0.8307(3) 0.7619(3) 0.01113(18) 0.0247(5) Uani 1 1 d . . . . .
C1 C 0.1190(3) 0.2365(3) 0.36447(19) 0.0252(5) Uani 1 1 d . . . . .
C12 C 0.3954(4) 0.4637(2) 0.17698(18) 0.0266(5) Uani 1 1 d . . . . .
H12 H 0.348527 0.392476 0.156264 0.032 Uiso 1 1 calc R U . . .
C2 C 0.2081(3) 0.1190(3) 0.31984(19) 0.0272(5) Uani 1 1 d . . . . .
H2 H 0.212971 0.133845 0.248108 0.033 Uiso 1 1 calc R U . . .
C3 C 0.1035(3) 0.2184(3) 0.47513(19) 0.0282(6) Uani 1 1 d . . . . .
C17 C 0.8492(3) 0.6335(3) 0.10239(19) 0.0267(5) Uani 1 1 d . . . . .
H17A H 0.908238 0.660737 0.150936 0.032 Uiso 1 1 calc R U . . .
H17B H 0.935432 0.542834 0.079314 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2860(4) -0.0427(3) 0.4714(2) 0.0299(6) Uani 1 1 d . . . . .
C16 C 0.3552(4) 0.6433(3) 0.28258(19) 0.0287(6) Uani 1 1 d . . . . .
H16 H 0.279654 0.695620 0.334966 0.034 Uiso 1 1 calc R U . . .
C4 C 0.1959(4) 0.0698(3) 0.52673(19) 0.0295(6) Uani 1 1 d . . . . .
C15 C 0.5360(4) 0.6725(3) 0.23444(19) 0.0297(6) Uani 1 1 d . . . . .
H15 H 0.582998 0.744481 0.254281 0.036 Uiso 1 1 calc R U . . .
C10 C 0.0243(4) 0.3841(3) 0.3045(2) 0.0288(6) Uani 1 1 d . . . . .
H10A H 0.043530 0.374984 0.232092 0.035 Uiso 1 1 calc R U . . .
H10B H -0.116953 0.401587 0.332898 0.035 Uiso 1 1 calc R U . . .
C19 C 0.7560(4) 1.0296(3) -0.0441(2) 0.0318(6) Uani 1 1 d . . . . .
H19A H 0.653336 1.027450 -0.079034 0.038 Uiso 1 1 calc R U . . .
H19B H 0.878300 1.033384 -0.095782 0.038 Uiso 1 1 calc R U . . .
C20 C 0.6996(4) 1.1640(3) 0.0054(2) 0.0368(6) Uani 1 1 d . . . . .
H20A H 0.689964 1.256856 -0.047958 0.055 Uiso 1 1 calc R U . . .
H20B H 0.798110 1.160731 0.043625 0.055 Uiso 1 1 calc R U . . .
H20C H 0.574014 1.162322 0.052758 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3767(4) -0.1851(3) 0.5169(2) 0.0374(6) Uani 1 1 d . . . . .
H6 H 0.438066 -0.260335 0.477378 0.045 Uiso 1 1 calc R U . . .
C9 C 0.1961(4) 0.0366(3) 0.6326(2) 0.0407(7) Uani 1 1 d . . . . .
H9 H 0.134233 0.110922 0.672781 0.049 Uiso 1 1 calc R U . . .
C7 C 0.3755(4) -0.2145(4) 0.6208(2) 0.0457(7) Uani 1 1 d . U . . .
H7 H 0.436459 -0.311281 0.653299 0.055 Uiso 1 1 calc R U . . .
C8 C 0.2868(4) -0.1051(4) 0.6783(2) 0.0479(7) Uani 1 1 d . U . . .
H8 H 0.288091 -0.127253 0.749736 0.057 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
O4 C18 1.337(3) . ?
O4 C19 1.459(3) . ?
O1 C2 1.354(3) . ?
O1 C5 1.376(3) . ?
O3 C18 1.204(3) . ?
O2 C3 1.231(3) . ?
N1 H1 0.8800 . ?
N1 C11 1.380(3) . ?
N1 C10 1.456(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(3) . ?
C13 C12 1.384(3) . ?
C11 C12 1.408(3) . ?
C11 C16 1.406(3) . ?
C14 C17 1.515(3) . ?
C14 C15 1.401(3) . ?
C18 C17 1.501(3) . ?
C1 C2 1.337(3) . ?
C1 C3 1.461(3) . ?
C1 C10 1.507(3) . ?
C12 H12 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.463(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C5 C4 1.387(4) . ?
C5 C6 1.390(4) . ?
C16 H16 0.9500 . ?
C16 C15 1.376(3) . ?
C4 C9 1.405(4) . ?
C15 H15 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.499(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C6 H6 0.9500 . ?
C6 C7 1.377(4) . ?
C9 H9 0.9500 . ?
C9 C8 1.385(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(5) . ?
C8 H8 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
C18 O4 C19 116.74(19) . . ?
C2 O1 C5 117.78(19) . . ?
C11 N1 H1 118.6 . . ?
C11 N1 C10 122.9(2) . . ?
C10 N1 H1 118.6 . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C12 C13 C14 122.2(2) . . ?
N1 C11 C12 123.8(2) . . ?
N1 C11 C16 118.5(2) . . ?
C16 C11 C12 117.6(2) . . ?
C13 C14 C17 121.6(2) . . ?
C13 C14 C15 117.4(2) . . ?
C15 C14 C17 120.9(2) . . ?
O4 C18 C17 111.8(2) . . ?
O3 C18 O4 123.0(2) . . ?
O3 C18 C17 125.1(2) . . ?
C2 C1 C3 119.1(2) . . ?
C2 C1 C10 121.5(2) . . ?
C3 C1 C10 119.3(2) . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
O1 C2 H2 117.0 . . ?
C1 C2 O1 126.0(2) . . ?
C1 C2 H2 117.0 . . ?
O2 C3 C1 121.7(2) . . ?
O2 C3 C4 123.2(2) . . ?
C1 C3 C4 115.1(2) . . ?
C14 C17 H17A 109.6 . . ?
C14 C17 H17B 109.6 . . ?
C18 C17 C14 110.48(19) . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
O1 C5 C4 121.7(2) . . ?
O1 C5 C6 116.0(2) . . ?
C4 C5 C6 122.3(3) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 C11 121.3(2) . . ?
C15 C16 H16 119.4 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 C9 118.2(2) . . ?
C9 C4 C3 121.6(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(2) . . ?
C16 C15 H15 119.4 . . ?
N1 C10 C1 114.8(2) . . ?
N1 C10 H10A 108.6 . . ?
N1 C10 H10B 108.6 . . ?
C1 C10 H10A 108.6 . . ?
C1 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
O4 C19 H19A 110.4 . . ?
O4 C19 H19B 110.4 . . ?
O4 C19 C20 106.6(2) . . ?
H19A C19 H19B 108.6 . . ?
C20 C19 H19A 110.4 . . ?
C20 C19 H19B 110.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C5 C6 H6 120.8 . . ?
C7 C6 C5 118.3(3) . . ?
C7 C6 H6 120.8 . . ?
C4 C9 H9 120.1 . . ?
C8 C9 C4 119.7(3) . . ?
C8 C9 H9 120.1 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 120.9(3) . . ?
C8 C7 H7 119.5 . . ?
C9 C8 H8 119.7 . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?

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
O4 C18 C17 C14 82.7(2) . . . . ?
O1 C5 C4 C3 0.0(3) . . . . ?
O1 C5 C4 C9 179.9(2) . . . . ?
O1 C5 C6 C7 179.9(2) . . . . ?
O3 C18 C17 C14 -96.0(3) . . . . ?
O2 C3 C4 C5 177.7(2) . . . . ?
O2 C3 C4 C9 -2.2(4) . . . . ?
N1 C11 C12 C13 178.9(2) . . . . ?
N1 C11 C16 C15 -178.9(2) . . . . ?
C13 C14 C17 C18 89.8(3) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C11 N1 C10 C1 69.3(3) . . . . ?
C11 C16 C15 C14 0.1(4) . . . . ?
C14 C13 C12 C11 -0.3(4) . . . . ?
C18 O4 C19 C20 179.51(19) . . . . ?
C1 C3 C4 C5 -1.3(3) . . . . ?
C1 C3 C4 C9 178.8(2) . . . . ?
C12 C13 C14 C17 -178.5(2) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C12 C11 C16 C15 -0.7(4) . . . . ?
C2 O1 C5 C4 0.7(3) . . . . ?
C2 O1 C5 C6 -178.9(2) . . . . ?
C2 C1 C3 O2 -177.1(2) . . . . ?
C2 C1 C3 C4 2.0(3) . . . . ?
C2 C1 C10 N1 -122.6(2) . . . . ?
C3 C1 C2 O1 -1.5(4) . . . . ?
C3 C1 C10 N1 61.1(3) . . . . ?
C3 C4 C9 C8 -179.4(2) . . . . ?
C17 C14 C15 C16 178.6(2) . . . . ?
C5 O1 C2 C1 0.0(3) . . . . ?
C5 C4 C9 C8 0.7(4) . . . . ?
C5 C6 C7 C8 -0.2(4) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C4 C9 C8 C7 -0.6(4) . . . . ?
C15 C14 C17 C18 -88.4(3) . . . . ?
C10 N1 C11 C12 18.5(4) . . . . ?
C10 N1 C11 C16 -163.4(2) . . . . ?
C10 C1 C2 O1 -177.8(2) . . . . ?
C10 C1 C3 O2 -0.7(3) . . . . ?
C10 C1 C3 C4 178.43(19) . . . . ?
C19 O4 C18 O3 -0.4(3) . . . . ?
C19 O4 C18 C17 -179.14(19) . . . . ?
C6 C5 C4 C3 179.6(2) . . . . ?
C6 C5 C4 C9 -0.5(4) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
