# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 2369017'
loop_
_audit_author_name
_audit_author_address
'Feng Zhao'
;Hunan University of Medicine
China
;
_audit_update_record             
;
2025-11-28 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2024-06-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N O'
_chemical_formula_sum            'C20 H17 N O'
_chemical_formula_weight         287.35
_chemical_absolute_configuration ?
_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      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                   7.9657(4)
_cell_length_b                   11.4669(5)
_cell_length_c                   15.8658(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1449.21(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9493
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0888 before and 0.0650 after correction.
The Ratio of minimum to maximum transmission is 0.8484.
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    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13384
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.470
_diffrn_reflns_theta_min         2.568
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2807
_reflns_number_total             2990
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.6(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2990
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.044
_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)+(0.0410P)²+0.3388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0866
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: -0.6(18)
 1.6(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C16(H16),
 C17(H17), C18(H18), N1(H1A)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), 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
C1 C 1.0548(3) -0.01288(18) 0.68683(12) 0.0187(4) Uani 1 1 d . . . . .
H1 H 1.113354 0.059028 0.691391 0.022 Uiso 1 1 calc R U . . .
C2 C 1.1305(3) -0.11481(18) 0.71444(13) 0.0217(5) Uani 1 1 d . . . . .
H2 H 1.239701 -0.112241 0.738459 0.026 Uiso 1 1 calc R U . . .
C3 C 1.0471(3) -0.22065(18) 0.70708(13) 0.0232(5) Uani 1 1 d . . . . .
H3 H 1.098683 -0.290371 0.726481 0.028 Uiso 1 1 calc R U . . .
C4 C 0.8880(3) -0.22426(19) 0.67123(13) 0.0231(5) Uani 1 1 d . . . . .
H4 H 0.831342 -0.296695 0.665193 0.028 Uiso 1 1 calc R U . . .
C5 C 0.8117(3) -0.12187(17) 0.64424(13) 0.0203(4) Uani 1 1 d . . . . .
H5 H 0.702787 -0.124944 0.619996 0.024 Uiso 1 1 calc R U . . .
C6 C 0.8928(2) -0.01474(17) 0.65222(12) 0.0162(4) Uani 1 1 d . . . . .
C7 C 0.8127(3) 0.09543(16) 0.62687(12) 0.0162(4) Uani 1 1 d . . . . .
C8 C 0.6536(2) 0.13801(16) 0.64272(12) 0.0150(4) Uani 1 1 d . . . . .
C9 C 0.5173(3) 0.07578(18) 0.69010(13) 0.0199(4) Uani 1 1 d . . . . .
H9A H 0.425835 0.056047 0.651336 0.030 Uiso 1 1 calc R U . . .
H9B H 0.474450 0.126481 0.734924 0.030 Uiso 1 1 calc R U . . .
H9C H 0.562659 0.004169 0.714970 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6507(2) 0.25569(16) 0.61049(12) 0.0141(4) Uani 1 1 d . . . . .
C11 C 0.8097(3) 0.27782(16) 0.57588(12) 0.0151(4) Uani 1 1 d . . . . .
C12 C 0.8539(2) 0.38421(17) 0.53764(13) 0.0171(4) Uani 1 1 d . . . . .
H12 H 0.960628 0.394702 0.512017 0.021 Uiso 1 1 calc R U . . .
C13 C 0.7377(2) 0.47190(17) 0.53874(12) 0.0170(4) Uani 1 1 d . . . . .
H13 H 0.765815 0.545287 0.514830 0.020 Uiso 1 1 calc R U . . .
C14 C 0.5749(2) 0.45613(17) 0.57489(12) 0.0151(4) Uani 1 1 d . . . . .
C15 C 0.4565(3) 0.54937(17) 0.57494(12) 0.0165(4) Uani 1 1 d . . . . .
C16 C 0.2956(3) 0.53335(17) 0.60380(13) 0.0190(4) Uani 1 1 d . . . . .
H16 H 0.217044 0.595636 0.602297 0.023 Uiso 1 1 calc R U . . .
C17 C 0.2486(2) 0.42362(17) 0.63562(13) 0.0193(4) Uani 1 1 d . . . . .
H17 H 0.136977 0.412337 0.655132 0.023 Uiso 1 1 calc R U . . .
C18 C 0.3597(2) 0.33269(17) 0.63914(12) 0.0171(4) Uani 1 1 d . . . . .
H18 H 0.324899 0.259900 0.661778 0.021 Uiso 1 1 calc R U . . .
C19 C 0.5261(2) 0.34620(16) 0.60935(12) 0.0149(4) Uani 1 1 d . . . . .
C20 C 0.4102(3) 0.75168(18) 0.54986(14) 0.0235(5) Uani 1 1 d . . . . .
H20A H 0.306398 0.735736 0.518811 0.035 Uiso 1 1 calc R U . . .
H20B H 0.466451 0.819622 0.525214 0.035 Uiso 1 1 calc R U . . .
H20C H 0.383539 0.767618 0.609050 0.035 Uiso 1 1 calc R U . . .
N1 N 0.9064(2) 0.18070(14) 0.58753(10) 0.0169(4) Uani 1 1 d . . . . .
H1A H 1.012140 0.173666 0.572282 0.020 Uiso 1 1 calc R U . . .
O1 O 0.51844(18) 0.65280(12) 0.54480(9) 0.0212(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
C1 H1 0.9500 . ?
C1 C2 1.386(3) . ?
C1 C6 1.403(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(3) . ?
C6 C7 1.471(3) . ?
C7 C8 1.381(3) . ?
C7 N1 1.379(2) . ?
C8 C9 1.501(3) . ?
C8 C10 1.443(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.404(3) . ?
C10 C19 1.436(3) . ?
C11 C12 1.407(3) . ?
C11 N1 1.367(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.367(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.429(3) . ?
C14 C15 1.426(3) . ?
C14 C19 1.428(3) . ?
C15 C16 1.373(3) . ?
C15 O1 1.371(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.407(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.369(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.416(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 O1 1.426(2) . ?
N1 H1A 0.8800 . ?

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 119.6 . . ?
C2 C1 C6 120.7(2) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.16(19) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.78(19) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.97(19) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 119.53(18) . . ?
C5 C6 C1 118.37(18) . . ?
C5 C6 C7 122.10(17) . . ?
C8 C7 C6 130.66(18) . . ?
N1 C7 C6 119.86(17) . . ?
N1 C7 C8 109.16(16) . . ?
C7 C8 C9 125.93(17) . . ?
C7 C8 C10 106.32(17) . . ?
C10 C8 C9 127.59(17) . . ?
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 . . ?
C11 C10 C8 107.03(16) . . ?
C11 C10 C19 119.20(16) . . ?
C19 C10 C8 133.75(17) . . ?
C10 C11 C12 123.46(17) . . ?
N1 C11 C10 107.98(16) . . ?
N1 C11 C12 128.56(18) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 C11 117.55(17) . . ?
C13 C12 H12 121.2 . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.77(18) . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 120.37(17) . . ?
C15 C14 C19 118.79(17) . . ?
C19 C14 C13 120.82(17) . . ?
C16 C15 C14 121.15(18) . . ?
O1 C15 C14 114.23(16) . . ?
O1 C15 C16 124.62(18) . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.22(18) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.57(18) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.57(18) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C10 117.04(16) . . ?
C18 C19 C10 124.30(17) . . ?
C18 C19 C14 118.65(17) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
C7 N1 H1A 125.3 . . ?
C11 N1 C7 109.49(16) . . ?
C11 N1 H1A 125.3 . . ?
C15 O1 C20 116.78(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
C1 C2 C3 C4 0.6(3) . . . . ?
C1 C6 C7 C8 -132.6(2) . . . . ?
C1 C6 C7 N1 40.1(3) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C1 C6 C7 177.33(18) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C4 C5 C6 C7 -177.85(19) . . . . ?
C5 C6 C7 C8 46.4(3) . . . . ?
C5 C6 C7 N1 -140.87(19) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C6 C7 C8 C9 -2.1(3) . . . . ?
C6 C7 C8 C10 173.74(19) . . . . ?
C6 C7 N1 C11 -175.36(16) . . . . ?
C7 C8 C10 C11 0.5(2) . . . . ?
C7 C8 C10 C19 -178.2(2) . . . . ?
C8 C7 N1 C11 -1.2(2) . . . . ?
C8 C10 C11 C12 179.52(18) . . . . ?
C8 C10 C11 N1 -1.2(2) . . . . ?
C8 C10 C19 C14 176.46(19) . . . . ?
C8 C10 C19 C18 -4.2(3) . . . . ?
C9 C8 C10 C11 176.17(19) . . . . ?
C9 C8 C10 C19 -2.5(3) . . . . ?
C10 C11 C12 C13 3.6(3) . . . . ?
C10 C11 N1 C7 1.5(2) . . . . ?
C11 C10 C19 C14 -2.0(3) . . . . ?
C11 C10 C19 C18 177.31(18) . . . . ?
C11 C12 C13 C14 -1.9(3) . . . . ?
C12 C11 N1 C7 -179.27(19) . . . . ?
C12 C13 C14 C15 -179.94(18) . . . . ?
C12 C13 C14 C19 -1.8(3) . . . . ?
C13 C14 C15 C16 175.21(18) . . . . ?
C13 C14 C15 O1 -5.2(3) . . . . ?
C13 C14 C19 C10 3.7(3) . . . . ?
C13 C14 C19 C18 -175.70(17) . . . . ?
C14 C15 C16 C17 1.5(3) . . . . ?
C14 C15 O1 C20 -174.89(16) . . . . ?
C15 C14 C19 C10 -178.12(17) . . . . ?
C15 C14 C19 C18 2.5(3) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C16 C15 O1 C20 4.7(3) . . . . ?
C16 C17 C18 C19 -1.0(3) . . . . ?
C17 C18 C19 C10 -179.90(19) . . . . ?
C17 C18 C19 C14 -0.6(3) . . . . ?
C19 C10 C11 C12 -1.6(3) . . . . ?
C19 C10 C11 N1 177.67(16) . . . . ?
C19 C14 C15 C16 -3.0(3) . . . . ?
C19 C14 C15 O1 176.59(17) . . . . ?
N1 C7 C8 C9 -175.36(18) . . . . ?
N1 C7 C8 C10 0.4(2) . . . . ?
N1 C11 C12 C13 -175.53(19) . . . . ?
O1 C15 C16 C17 -178.07(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 -0.6(18)
2 1.6(18)

