# Supplementary Information (SI) for ChemComm.
# 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 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_1_a
_database_code_depnum_ccdc_archive 'CCDC 2473864'
loop_
_audit_author_name
_audit_author_address
'Qinghe Gao'
;Xinxiang Medical University
China
;
_audit_update_record             
;
2025-07-18 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_audit_creation_date             2024-09-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 N O2'
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36
_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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.204(14)
_cell_length_b                   6.943(7)
_cell_length_c                   15.282(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1613(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3715
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.88
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6614
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0680 before and 0.0594 after correction.
The Ratio of minimum to maximum transmission is 0.8875.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20639
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.094
_diffrn_reflns_theta_max         25.094
_diffrn_reflns_theta_min         2.666
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                965
_reflns_number_total             1552
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1552
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.033
_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)+(0.0663P)²+0.4086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1452
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 0.4945(2) 0.7500 0.5772(2) 0.0554(8) Uani 1 2 d S T P . .
C2 C 0.5659(3) 0.7500 0.6323(2) 0.0694(10) Uani 1 2 d S T P . .
H2 H 0.5584 0.7500 0.6927 0.083 Uiso 1 2 calc R U P . .
C3 C 0.6479(3) 0.7500 0.5964(3) 0.0762(11) Uani 1 2 d S T P . .
H3 H 0.6970 0.7500 0.6327 0.091 Uiso 1 2 calc R U P . .
C4 C 0.6590(2) 0.7500 0.5066(3) 0.0731(10) Uani 1 2 d S T P . .
H4 H 0.7153 0.7500 0.4828 0.088 Uiso 1 2 calc R U P . .
C5 C 0.58723(19) 0.7500 0.4526(2) 0.0603(9) Uani 1 2 d S T P . .
H5 H 0.5951 0.7500 0.3923 0.072 Uiso 1 2 calc R U P . .
C6 C 0.5029(2) 0.7500 0.48707(19) 0.0492(7) Uani 1 2 d S T P . .
C7 C 0.42373(17) 0.7500 0.43443(19) 0.0466(7) Uani 1 2 d S T P . .
C8 C 0.34345(19) 0.7500 0.47580(17) 0.0517(8) Uani 1 2 d S T P . .
C9 C 0.3370(2) 0.7500 0.5715(2) 0.0662(9) Uani 1 2 d S T P . .
C10 C 0.2680(2) 0.7500 0.42544(19) 0.0610(9) Uani 1 2 d S T P . .
H10 H 0.2133 0.7500 0.4526 0.073 Uiso 1 2 calc R U P . .
C11 C 0.27282(18) 0.7500 0.33497(18) 0.0531(8) Uani 1 2 d S T P . .
C12 C 0.35768(18) 0.7500 0.29873(18) 0.0482(7) Uani 1 2 d S T P . .
C13 C 0.37300(17) 0.7500 0.20194(18) 0.0494(8) Uani 1 2 d S T P . .
C14 C 0.38151(17) 0.5821(4) 0.15666(15) 0.0774(8) Uani 1 1 d . . . . .
H14 H 0.3746 0.4655 0.1858 0.093 Uiso 1 1 calc R U . . .
C15 C 0.40022(17) 0.5822(5) 0.06811(17) 0.0884(9) Uani 1 1 d . . . . .
H15 H 0.4062 0.4660 0.0384 0.106 Uiso 1 1 calc R U . . .
C16 C 0.4099(2) 0.7500 0.0245(2) 0.0786(12) Uani 1 2 d S T P . .
H16 H 0.4231 0.7500 -0.0349 0.094 Uiso 1 2 calc R U P . .
C17 C 0.19058(19) 0.7500 0.27993(19) 0.0627(9) Uani 1 2 d S T P . .
H17 H 0.2085 0.7500 0.2183 0.075 Uiso 1 2 calc R U P . .
C18 C 0.13627(18) 0.5719(5) 0.29561(19) 0.1031(10) Uani 1 1 d . . . . .
H18A H 0.1702 0.4599 0.2808 0.155 Uiso 1 1 calc R U . . .
H18B H 0.0844 0.5763 0.2599 0.155 Uiso 1 1 calc R U . . .
H18C H 0.1196 0.5658 0.3561 0.155 Uiso 1 1 calc R U . . .
N1 N 0.43119(15) 0.7500 0.34637(15) 0.0487(6) Uani 1 2 d S T P . .
O1 O 0.41318(15) 0.7500 0.61778(12) 0.0676(7) Uani 1 2 d S T P . .
O2 O 0.26949(17) 0.7500 0.61242(14) 0.0915(9) Uani 1 2 d S T P . .


_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 C2 1.374(4) . ?
C1 C6 1.383(4) . ?
C1 O1 1.384(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.362(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(4) . ?
C6 C7 1.448(4) . ?
C7 C8 1.375(4) . ?
C7 N1 1.350(4) . ?
C8 C9 1.465(4) . ?
C8 C10 1.382(4) . ?
C9 O1 1.357(4) . ?
C9 O2 1.202(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(4) . ?
C11 C12 1.404(4) . ?
C11 C17 1.507(4) . ?
C12 C13 1.497(4) . ?
C12 N1 1.334(3) . ?
C13 C14 1.362(3) 7_575 ?
C13 C14 1.362(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.351(3) . ?
C16 C15 1.351(3) 7_575 ?
C16 H16 0.9300 . ?
C17 H17 0.9800 . ?
C17 C18 1.506(3) 7_575 ?
C17 C18 1.506(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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 C6 122.6(3) . . ?
C2 C1 O1 115.5(3) . . ?
C6 C1 O1 121.9(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.6(3) . . ?
C1 C6 C7 118.5(3) . . ?
C5 C6 C7 123.9(3) . . ?
C8 C7 C6 118.9(3) . . ?
N1 C7 C6 118.9(3) . . ?
N1 C7 C8 122.2(3) . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 C10 118.8(3) . . ?
C10 C8 C9 120.0(3) . . ?
O1 C9 C8 117.6(3) . . ?
O2 C9 C8 125.2(3) . . ?
O2 C9 O1 117.2(3) . . ?
C8 C10 H10 119.6 . . ?
C8 C10 C11 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 116.3(3) . . ?
C10 C11 C17 120.9(3) . . ?
C12 C11 C17 122.8(3) . . ?
C11 C12 C13 122.2(2) . . ?
N1 C12 C11 123.7(3) . . ?
N1 C12 C13 114.1(2) . . ?
C14 C13 C12 121.12(15) 7_575 . ?
C14 C13 C12 121.11(15) . . ?
C14 C13 C14 117.7(3) . 7_575 ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.1(3) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C15 119.3(3) . 7_575 ?
C15 C16 H16 120.4 . . ?
C15 C16 H16 120.4 7_575 . ?
C11 C17 H17 107.8 . . ?
C18 C17 C11 111.47(17) . . ?
C18 C17 C11 111.47(17) 7_575 . ?
C18 C17 H17 107.8 . . ?
C18 C17 H17 107.8 7_575 . ?
C18 C17 C18 110.4(3) . 7_575 ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C12 N1 C7 118.3(2) . . ?
C9 O1 C1 121.9(2) . . ?

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 0.000(1) . . . . ?
C1 C6 C7 C8 0.000(1) . . . . ?
C1 C6 C7 N1 180.000(0) . . . . ?
C2 C1 C6 C5 0.000(1) . . . . ?
C2 C1 C6 C7 180.000(1) . . . . ?
C2 C1 O1 C9 180.000(1) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
C4 C5 C6 C1 0.000(1) . . . . ?
C4 C5 C6 C7 180.000(0) . . . . ?
C5 C6 C7 C8 180.000(0) . . . . ?
C5 C6 C7 N1 0.000(0) . . . . ?
C6 C1 C2 C3 0.000(1) . . . . ?
C6 C1 O1 C9 0.000(1) . . . . ?
C6 C7 C8 C9 0.000(1) . . . . ?
C6 C7 C8 C10 180.000(0) . . . . ?
C6 C7 N1 C12 180.000(0) . . . . ?
C7 C8 C9 O1 0.000(1) . . . . ?
C7 C8 C9 O2 180.000(1) . . . . ?
C7 C8 C10 C11 0.000(0) . . . . ?
C8 C7 N1 C12 0.000(0) . . . . ?
C8 C9 O1 C1 0.000(1) . . . . ?
C8 C10 C11 C12 0.000(0) . . . . ?
C8 C10 C11 C17 180.000(0) . . . . ?
C9 C8 C10 C11 180.000(0) . . . . ?
C10 C8 C9 O1 180.000(0) . . . . ?
C10 C8 C9 O2 0.000(1) . . . . ?
C10 C11 C12 C13 180.000(0) . . . . ?
C10 C11 C12 N1 0.000(0) . . . . ?
C10 C11 C17 C18 61.9(2) . . . 7_575 ?
C10 C11 C17 C18 -61.9(2) . . . . ?
C11 C12 C13 C14 -91.0(2) . . . . ?
C11 C12 C13 C14 91.0(2) . . . 7_575 ?
C11 C12 N1 C7 0.000(0) . . . . ?
C12 C11 C17 C18 118.1(2) . . . . ?
C12 C11 C17 C18 -118.1(2) . . . 7_575 ?
C12 C13 C14 C15 -176.6(2) . . . . ?
C13 C12 N1 C7 180.000(0) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C14 C13 C14 C15 1.5(5) 7_575 . . . ?
C14 C15 C16 C15 -0.7(6) . . . 7_575 ?
C17 C11 C12 C13 0.000(0) . . . . ?
C17 C11 C12 N1 180.000(0) . . . . ?
N1 C7 C8 C9 180.000(0) . . . . ?
N1 C7 C8 C10 0.000(1) . . . . ?
N1 C12 C13 C14 -89.0(2) . . . 7_575 ?
N1 C12 C13 C14 89.0(2) . . . . ?
O1 C1 C2 C3 180.000(1) . . . . ?
O1 C1 C6 C5 180.000(1) . . . . ?
O1 C1 C6 C7 0.000(1) . . . . ?
O2 C9 O1 C1 180.000(1) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
