# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 2476281'
loop_
_audit_author_name
_audit_author_address
'Dengke Ma'
;Capital Medical University
China
;
_audit_update_record             
;
2025-07-27 deposited with the CCDC.	2025-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 N O2'
_chemical_formula_weight         341.39

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   9.6716(2)
_cell_length_b                   16.7005(5)
_cell_length_c                   11.2891(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1823.42(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    180.00(10)
_cell_measurement_reflns_used    13293
_cell_measurement_theta_min      2.1600
_cell_measurement_theta_max      30.3370

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.57816
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.729
_oxdiff_exptl_absorpt_empirical_full_max 1.503
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      180.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       ?
_diffrn_reflns_number            21102
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.178
_diffrn_reflns_theta_max         30.729
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5033
_reflns_number_gt                4248
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_max     0.843
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0514P)²+0.0379P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1712 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5033
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0928
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.77076(12) 0.62755(7) 0.59971(11) 0.0373(3) Uani 1 1 d . . . . .
O2 O 1.01004(12) 0.76764(10) 0.42031(12) 0.0510(4) Uani 1 1 d . . . . .
N1 N 0.79231(14) 0.73177(10) 0.46380(14) 0.0411(4) Uani 1 1 d . . . . .
H1 H 0.7065 0.7287 0.4384 0.049 Uiso 1 1 calc R U . . .
C18 C 0.56588(15) 0.57973(9) 0.70306(15) 0.0323(3) Uani 1 1 d . . . . .
C12 C 0.80479(16) 0.57419(10) 0.79537(15) 0.0343(3) Uani 1 1 d . . . . .
C1 C 0.88964(16) 0.75878(9) 0.38953(15) 0.0340(3) Uani 1 1 d . . . . .
C2 C 0.84511(16) 0.77989(10) 0.26677(15) 0.0337(3) Uani 1 1 d . . . . .
C23 C 0.49888(18) 0.55170(12) 0.80399(17) 0.0406(4) Uani 1 1 d . . . . .
H23 H 0.5444 0.5545 0.8784 0.049 Uiso 1 1 calc R U . . .
C10 C 0.68672(19) 0.70708(10) 0.75117(16) 0.0374(4) Uani 1 1 d . . . . .
H10 H 0.6351 0.7243 0.8181 0.045 Uiso 1 1 calc R U . . .
C11 C 0.70638(16) 0.62076(9) 0.71491(15) 0.0320(3) Uani 1 1 d . . . . .
C19 C 0.49822(17) 0.57453(10) 0.59475(17) 0.0381(4) Uani 1 1 d . . . . .
H19 H 0.5419 0.5934 0.5248 0.046 Uiso 1 1 calc R U . . .
C9 C 0.7511(2) 0.75508(11) 0.67702(17) 0.0426(4) Uani 1 1 d . . . . .
H9 H 0.7522 0.8119 0.6823 0.051 Uiso 1 1 calc R U . . .
C8 C 0.82206(17) 0.70743(11) 0.58370(16) 0.0396(4) Uani 1 1 d . . . . .
H8 H 0.9242 0.7084 0.5974 0.048 Uiso 1 1 calc R U . . .
C17 C 0.83815(18) 0.49590(11) 0.7658(2) 0.0437(4) Uani 1 1 d . . . . .
H17 H 0.7981 0.4722 0.6974 0.052 Uiso 1 1 calc R U . . .
C3 C 0.91163(18) 0.84236(10) 0.20936(18) 0.0401(4) Uani 1 1 d . . . . .
H3 H 0.9819 0.8716 0.2492 0.048 Uiso 1 1 calc R U . . .
C22 C 0.36680(18) 0.51971(12) 0.7976(2) 0.0471(4) Uani 1 1 d . . . . .
H22 H 0.3220 0.5016 0.8676 0.057 Uiso 1 1 calc R U . . .
C21 C 0.30059(19) 0.51424(11) 0.6901(2) 0.0481(5) Uani 1 1 d . . . . .
H21 H 0.2105 0.4919 0.6854 0.058 Uiso 1 1 calc R U . . .
C4 C 0.8763(2) 0.86230(10) 0.09429(19) 0.0460(4) Uani 1 1 d . . . . .
H4 H 0.9224 0.9052 0.0556 0.055 Uiso 1 1 calc R U . . .
C5 C 0.7753(2) 0.82074(14) 0.03593(17) 0.0508(5) Uani 1 1 d . . . . .
H5 H 0.7520 0.8343 -0.0433 0.061 Uiso 1 1 calc R U . . .
C20 C 0.36594(18) 0.54149(11) 0.58907(19) 0.0460(4) Uani 1 1 d . . . . .
H20 H 0.3202 0.5377 0.5148 0.055 Uiso 1 1 calc R U . . .
C13 C 0.86488(19) 0.60745(12) 0.89519(19) 0.0471(4) Uani 1 1 d . . . . .
H13 H 0.8440 0.6611 0.9166 0.056 Uiso 1 1 calc R U . . .
C7 C 0.7429(2) 0.73834(13) 0.20738(18) 0.0483(5) Uani 1 1 d . . . . .
H7 H 0.6967 0.6953 0.2455 0.058 Uiso 1 1 calc R U . . .
C16 C 0.9292(2) 0.45188(13) 0.8348(2) 0.0560(5) Uani 1 1 d . . . . .
H16 H 0.9513 0.3984 0.8134 0.067 Uiso 1 1 calc R U . . .
C14 C 0.9558(2) 0.56285(15) 0.9645(2) 0.0584(6) Uani 1 1 d . . . . .
H14 H 0.9958 0.5862 1.0331 0.070 Uiso 1 1 calc R U . . .
C15 C 0.9879(2) 0.48560(15) 0.9345(2) 0.0569(6) Uani 1 1 d . . . . .
H15 H 1.0502 0.4555 0.9820 0.068 Uiso 1 1 calc R U . . .
C6 C 0.7076(3) 0.75910(15) 0.0926(2) 0.0607(6) Uani 1 1 d . . . . .
H6 H 0.6363 0.7307 0.0528 0.073 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
O1 C8 1.435(2) . ?
O1 C11 1.446(2) . ?
O2 C1 1.224(2) . ?
N1 C1 1.339(2) . ?
N1 C8 1.442(2) . ?
N1 H1 0.8800 . ?
C18 C19 1.390(2) . ?
C18 C23 1.392(3) . ?
C18 C11 1.528(2) . ?
C12 C13 1.384(3) . ?
C12 C17 1.387(3) . ?
C12 C11 1.528(2) . ?
C1 C2 1.493(2) . ?
C2 C7 1.381(3) . ?
C2 C3 1.386(2) . ?
C23 C22 1.386(3) . ?
C23 H23 0.9500 . ?
C10 C9 1.316(3) . ?
C10 C11 1.511(2) . ?
C10 H10 0.9500 . ?
C19 C20 1.395(3) . ?
C19 H19 0.9500 . ?
C9 C8 1.488(3) . ?
C9 H9 0.9500 . ?
C8 H8 1.0000 . ?
C17 C16 1.387(3) . ?
C17 H17 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C22 C21 1.376(3) . ?
C22 H22 0.9500 . ?
C21 C20 1.381(3) . ?
C21 H21 0.9500 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C20 H20 0.9500 . ?
C13 C14 1.393(3) . ?
C13 H13 0.9500 . ?
C7 C6 1.384(3) . ?
C7 H7 0.9500 . ?
C16 C15 1.381(3) . ?
C16 H16 0.9500 . ?
C14 C15 1.369(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C6 H6 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
C8 O1 C11 109.57(12) . . ?
C1 N1 C8 122.85(14) . . ?
C1 N1 H1 118.6 . . ?
C8 N1 H1 118.6 . . ?
C19 C18 C23 118.69(15) . . ?
C19 C18 C11 121.59(15) . . ?
C23 C18 C11 119.56(15) . . ?
C13 C12 C17 118.45(16) . . ?
C13 C12 C11 122.76(16) . . ?
C17 C12 C11 118.78(16) . . ?
O2 C1 N1 122.12(17) . . ?
O2 C1 C2 120.60(15) . . ?
N1 C1 C2 117.26(14) . . ?
C7 C2 C3 118.88(17) . . ?
C7 C2 C1 122.56(15) . . ?
C3 C2 C1 118.54(15) . . ?
C22 C23 C18 121.08(18) . . ?
C22 C23 H23 119.5 . . ?
C18 C23 H23 119.5 . . ?
C9 C10 C11 110.45(16) . . ?
C9 C10 H10 124.8 . . ?
C11 C10 H10 124.8 . . ?
O1 C11 C10 102.89(13) . . ?
O1 C11 C18 109.84(13) . . ?
C10 C11 C18 109.87(13) . . ?
O1 C11 C12 107.83(13) . . ?
C10 C11 C12 113.77(14) . . ?
C18 C11 C12 112.18(13) . . ?
C18 C19 C20 119.81(17) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C10 C9 C8 110.05(16) . . ?
C10 C9 H9 125.0 . . ?
C8 C9 H9 125.0 . . ?
O1 C8 N1 108.14(15) . . ?
O1 C8 C9 104.40(14) . . ?
N1 C8 C9 114.95(15) . . ?
O1 C8 H8 109.7 . . ?
N1 C8 H8 109.7 . . ?
C9 C8 H8 109.7 . . ?
C16 C17 C12 120.8(2) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C4 C3 C2 120.34(17) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C21 C22 C23 120.00(19) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C21 C20 119.60(17) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C5 C4 C3 120.45(17) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.65(19) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C21 C20 C19 120.81(18) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C2 C7 C6 120.35(18) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 119.48(19) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C5 C6 C7 120.32(19) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?

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
C8 N1 C1 O2 -3.0(3) . . . . ?
C8 N1 C1 C2 178.42(16) . . . . ?
O2 C1 C2 C7 146.53(19) . . . . ?
N1 C1 C2 C7 -34.9(2) . . . . ?
O2 C1 C2 C3 -31.8(2) . . . . ?
N1 C1 C2 C3 146.83(16) . . . . ?
C19 C18 C23 C22 -0.5(3) . . . . ?
C11 C18 C23 C22 175.03(16) . . . . ?
C8 O1 C11 C10 15.65(15) . . . . ?
C8 O1 C11 C18 132.60(13) . . . . ?
C8 O1 C11 C12 -104.87(15) . . . . ?
C9 C10 C11 O1 -9.23(19) . . . . ?
C9 C10 C11 C18 -126.16(17) . . . . ?
C9 C10 C11 C12 107.13(17) . . . . ?
C19 C18 C11 O1 -18.1(2) . . . . ?
C23 C18 C11 O1 166.45(14) . . . . ?
C19 C18 C11 C10 94.35(18) . . . . ?
C23 C18 C11 C10 -81.06(19) . . . . ?
C19 C18 C11 C12 -138.05(16) . . . . ?
C23 C18 C11 C12 46.5(2) . . . . ?
C13 C12 C11 O1 116.25(18) . . . . ?
C17 C12 C11 O1 -62.13(19) . . . . ?
C13 C12 C11 C10 2.8(2) . . . . ?
C17 C12 C11 C10 -175.57(15) . . . . ?
C13 C12 C11 C18 -122.67(18) . . . . ?
C17 C12 C11 C18 58.9(2) . . . . ?
C23 C18 C19 C20 -0.2(2) . . . . ?
C11 C18 C19 C20 -175.61(15) . . . . ?
C11 C10 C9 C8 -0.5(2) . . . . ?
C11 O1 C8 N1 -139.00(13) . . . . ?
C11 O1 C8 C9 -16.15(17) . . . . ?
C1 N1 C8 O1 -125.74(17) . . . . ?
C1 N1 C8 C9 118.08(19) . . . . ?
C10 C9 C8 O1 10.2(2) . . . . ?
C10 C9 C8 N1 128.45(17) . . . . ?
C13 C12 C17 C16 0.2(3) . . . . ?
C11 C12 C17 C16 178.66(17) . . . . ?
C7 C2 C3 C4 -0.3(3) . . . . ?
C1 C2 C3 C4 178.10(15) . . . . ?
C18 C23 C22 C21 0.9(3) . . . . ?
C23 C22 C21 C20 -0.6(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C22 C21 C20 C19 0.0(3) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C17 C12 C13 C14 -0.5(3) . . . . ?
C11 C12 C13 C14 -178.89(17) . . . . ?
C3 C2 C7 C6 -0.2(3) . . . . ?
C1 C2 C7 C6 -178.5(2) . . . . ?
C12 C17 C16 C15 0.1(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C17 C16 C15 C14 -0.2(3) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C2 C7 C6 C5 0.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.88 1.91 2.7738(18) 166.1 3_465

_refine_diff_density_max         0.115
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.036

