# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2423860'
loop_
_audit_author_name
_audit_author_address
'kun he'
;yunnan university of chemistry
China
;
_audit_update_record             
;
2025-02-14 deposited with the CCDC.	2025-05-30 downloaded from the CCDC.
;
_audit_creation_date             2024-12-25
_audit_creation_method           
;
FinalCif V89 by Daniel Kratzert, Freiburg 2024,
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2018/3
_diffrn_source_power             0.07
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C19 H15 N O3'
_chemical_formula_moiety         'C19 H15 N O3'
_chemical_formula_weight         305.32
_chemical_melting_point          ?
_exptl_crystal_colour_primary    colourless
_space_group_crystal_system      triclinic
_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 Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0995(8)
_cell_length_b                   9.5130(9)
_cell_length_c                   9.7237(9)
_cell_angle_alpha                77.734(3)
_cell_angle_beta                 66.596(3)
_cell_angle_gamma                77.558(3)
_cell_volume                     746.73(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.31
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7168
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1116 before and 0.0565 after correction.
The Ratio of minimum to maximum transmission is 0.9612.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            26849
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_theta_min         2.215
_diffrn_reflns_theta_max         28.321
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3701
_reflns_number_gt                3242
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+0.3580P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3701
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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 0.64977(10) 0.69514(9) 0.39353(9) 0.01661(18) Uani 1 1 d . . . . .
O2 O 0.41305(10) 0.84004(10) 0.48806(10) 0.0221(2) Uani 1 1 d . . . . .
O3 O 0.19481(11) 0.88038(9) 0.82758(10) 0.0206(2) Uani 1 1 d . . . . .
N1 N 0.58186(11) 0.50922(10) 0.64883(11) 0.0149(2) Uani 1 1 d . . . . .
C1 C 0.55136(13) 0.41354(12) 0.77987(13) 0.0147(2) Uani 1 1 d . . . . .
C2 C 0.67273(14) 0.29420(13) 0.79048(13) 0.0180(2) Uani 1 1 d . . . . .
H2 H 0.772287 0.281938 0.707137 0.022 Uiso 1 1 calc R U . . .
C3 C 0.64630(15) 0.19692(13) 0.92066(14) 0.0198(2) Uani 1 1 d . . . . .
H3 H 0.728611 0.118164 0.927296 0.024 Uiso 1 1 calc R U . . .
C4 C 0.49801(15) 0.21195(13) 1.04565(14) 0.0196(2) Uani 1 1 d . . . . .
H4 H 0.481290 0.142729 1.134687 0.024 Uiso 1 1 calc R U . . .
C5 C 0.37854(14) 0.32572(13) 1.03890(13) 0.0178(2) Uani 1 1 d . . . . .
H5 H 0.279285 0.335111 1.123055 0.021 Uiso 1 1 calc R U . . .
C6 C 0.40298(13) 0.42955(12) 0.90629(13) 0.0151(2) Uani 1 1 d . . . . .
C7 C 0.28658(14) 0.55120(12) 0.89311(13) 0.0159(2) Uani 1 1 d . . . . .
H7 H 0.186511 0.565970 0.975344 0.019 Uiso 1 1 calc R U . . .
C8 C 0.31748(13) 0.64817(12) 0.76193(13) 0.0147(2) Uani 1 1 d . . . . .
C9 C 0.19563(13) 0.78440(12) 0.76190(13) 0.0148(2) Uani 1 1 d . . . . .
C10 C 0.06970(13) 0.79242(12) 0.69780(12) 0.0145(2) Uani 1 1 d . . . . .
C11 C -0.04453(14) 0.91840(12) 0.70860(13) 0.0166(2) Uani 1 1 d . . . . .
H11 H -0.039976 0.993835 0.756401 0.020 Uiso 1 1 calc R U . . .
C12 C -0.16418(14) 0.93390(13) 0.65011(14) 0.0188(2) Uani 1 1 d . . . . .
H12 H -0.241337 1.019716 0.657384 0.023 Uiso 1 1 calc R U . . .
C13 C -0.17062(14) 0.82305(14) 0.58071(13) 0.0197(2) Uani 1 1 d . . . . .
H13 H -0.252145 0.833624 0.539914 0.024 Uiso 1 1 calc R U . . .
C14 C -0.05871(15) 0.69683(14) 0.57053(14) 0.0205(2) Uani 1 1 d . . . . .
H14 H -0.064932 0.621186 0.523962 0.025 Uiso 1 1 calc R U . . .
C15 C 0.06269(14) 0.68081(13) 0.62842(13) 0.0178(2) Uani 1 1 d . . . . .
H15 H 0.139814 0.594954 0.620776 0.021 Uiso 1 1 calc R U . . .
C16 C 0.46884(13) 0.62081(12) 0.64151(12) 0.0141(2) Uani 1 1 d . . . . .
C17 C 0.50553(13) 0.72987(12) 0.49977(13) 0.0154(2) Uani 1 1 d . . . . .
C18 C 0.69664(15) 0.80726(13) 0.26179(13) 0.0186(2) Uani 1 1 d . . . . .
H18A H 0.686077 0.901914 0.294359 0.022 Uiso 1 1 calc R U . . .
H18B H 0.626465 0.818227 0.203080 0.022 Uiso 1 1 calc R U . . .
C19 C 0.87037(15) 0.75866(15) 0.16666(15) 0.0240(3) Uani 1 1 d . . . . .
H19A H 0.907354 0.832245 0.078066 0.036 Uiso 1 1 calc R U . . .
H19B H 0.878647 0.666079 0.133251 0.036 Uiso 1 1 calc R U . . .
H19C H 0.938028 0.746061 0.226841 0.036 Uiso 1 1 calc R U . . .


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 C17 1.3342(14) . ?
O1 C18 1.4635(13) . ?
O2 C17 1.2103(14) . ?
O3 C9 1.2176(14) . ?
N1 C1 1.3654(15) . ?
N1 C16 1.3211(14) . ?
C1 C2 1.4211(16) . ?
C1 C6 1.4247(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.3685(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.4164(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.3701(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.4190(16) . ?
C6 C7 1.4121(15) . ?
C7 H7 0.9500 . ?
C7 C8 1.3726(16) . ?
C8 C9 1.5132(15) . ?
C8 C16 1.4247(15) . ?
C9 C10 1.4890(16) . ?
C10 C11 1.3991(15) . ?
C10 C15 1.3979(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.3849(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3896(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3900(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3948(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.5045(15) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5078(17) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C17 O1 C18 114.67(9) . . ?
C16 N1 C1 117.93(10) . . ?
N1 C1 C2 118.64(10) . . ?
N1 C1 C6 122.41(10) . . ?
C2 C1 C6 118.95(10) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.06(11) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.96(11) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.38(11) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.04(11) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.60(10) . . ?
C7 C6 C1 117.44(10) . . ?
C7 C6 C5 122.96(10) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.25(10) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C9 117.30(10) . . ?
C7 C8 C16 117.77(10) . . ?
C16 C8 C9 124.60(10) . . ?
O3 C9 C8 118.02(10) . . ?
O3 C9 C10 121.41(10) . . ?
C10 C9 C8 120.23(10) . . ?
C11 C10 C9 117.33(10) . . ?
C15 C10 C9 122.75(10) . . ?
C15 C10 C11 119.91(11) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.46(11) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.55(11) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.51(11) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.25(11) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 120.3 . . ?
C14 C15 C10 119.31(11) . . ?
C14 C15 H15 120.3 . . ?
N1 C16 C8 124.18(10) . . ?
N1 C16 C17 117.89(10) . . ?
C8 C16 C17 117.86(10) . . ?
O1 C17 C16 113.56(9) . . ?
O2 C17 O1 124.43(10) . . ?
O2 C17 C16 121.97(10) . . ?
O1 C18 H18A 110.3 . . ?
O1 C18 H18B 110.3 . . ?
O1 C18 C19 106.91(10) . . ?
H18A C18 H18B 108.6 . . ?
C19 C18 H18A 110.3 . . ?
C19 C18 H18B 110.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O3 C9 C10 C11 3.45(16) . . . . ?
O3 C9 C10 C15 -176.76(11) . . . . ?
N1 C1 C2 C3 179.56(11) . . . . ?
N1 C1 C6 C5 179.62(10) . . . . ?
N1 C1 C6 C7 -1.04(17) . . . . ?
N1 C16 C17 O1 2.86(15) . . . . ?
N1 C16 C17 O2 -174.94(11) . . . . ?
C1 N1 C16 C8 0.37(17) . . . . ?
C1 N1 C16 C17 177.27(10) . . . . ?
C1 C2 C3 C4 0.82(18) . . . . ?
C1 C6 C7 C8 0.50(17) . . . . ?
C2 C1 C6 C5 -0.76(17) . . . . ?
C2 C1 C6 C7 178.57(10) . . . . ?
C2 C3 C4 C5 -0.75(19) . . . . ?
C3 C4 C5 C6 -0.10(18) . . . . ?
C4 C5 C6 C1 0.85(17) . . . . ?
C4 C5 C6 C7 -178.45(11) . . . . ?
C5 C6 C7 C8 179.81(11) . . . . ?
C6 C1 C2 C3 -0.06(17) . . . . ?
C6 C7 C8 C9 -173.40(10) . . . . ?
C6 C7 C8 C16 0.39(17) . . . . ?
C7 C8 C9 O3 75.52(14) . . . . ?
C7 C8 C9 C10 -97.92(13) . . . . ?
C7 C8 C16 N1 -0.88(17) . . . . ?
C7 C8 C16 C17 -177.78(10) . . . . ?
C8 C9 C10 C11 176.66(10) . . . . ?
C8 C9 C10 C15 -3.55(16) . . . . ?
C8 C16 C17 O1 179.97(10) . . . . ?
C8 C16 C17 O2 2.16(16) . . . . ?
C9 C8 C16 N1 172.42(11) . . . . ?
C9 C8 C16 C17 -4.49(16) . . . . ?
C9 C10 C11 C12 179.38(10) . . . . ?
C9 C10 C15 C14 -179.73(10) . . . . ?
C10 C11 C12 C13 0.19(17) . . . . ?
C11 C10 C15 C14 0.05(17) . . . . ?
C11 C12 C13 C14 0.40(18) . . . . ?
C12 C13 C14 C15 -0.76(18) . . . . ?
C13 C14 C15 C10 0.53(18) . . . . ?
C15 C10 C11 C12 -0.42(17) . . . . ?
C16 N1 C1 C2 -179.00(10) . . . . ?
C16 N1 C1 C6 0.62(16) . . . . ?
C16 C8 C9 O3 -97.81(14) . . . . ?
C16 C8 C9 C10 88.76(14) . . . . ?
C17 O1 C18 C19 171.79(10) . . . . ?
C18 O1 C17 O2 4.55(16) . . . . ?
C18 O1 C17 C16 -173.19(9) . . . . ?

