# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2376866'
loop_
_audit_author_name
_audit_author_address
'Chengan Jin'
;Shaoxing University
China
;
_audit_update_record             
;
2024-08-11 deposited with the CCDC.	2025-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 N2 O'
_chemical_formula_sum            'C23 H18 N2 O'
_chemical_formula_weight         338.39

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.046(4)
_cell_length_b                   6.758(3)
_cell_length_c                   25.803(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.914(15)
_cell_angle_gamma                90
_cell_volume                     1742.5(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4025
_cell_measurement_theta_min      2.038
_cell_measurement_theta_max      27.578

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15747
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.038
_diffrn_reflns_theta_max         27.578
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4025
_reflns_number_gt                2099
_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       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1129P)²+0.3180P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.048(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3999
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1540
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.2338
_refine_ls_wR_factor_gt          0.1825
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
N1 N 0.3745(4) 0.7030(6) 0.54370(14) 0.0881(11) Uani 1 1 d . . . . .
C13 C 0.2132(3) 0.1604(4) 0.31274(11) 0.0389(7) Uani 1 1 d . . . . .
C12 C 0.1223(3) 0.1225(4) 0.35578(11) 0.0398(7) Uani 1 1 d . . . . .
C14 C 0.2317(3) 0.3850(4) 0.30631(11) 0.0455(8) Uani 1 1 d . . . . .
H14A H 0.301607 0.408794 0.283764 0.055 Uiso 1 1 calc R U . . .
H14B H 0.149393 0.441982 0.289837 0.055 Uiso 1 1 calc R U . . .
C7 C 0.1258(3) 0.2532(4) 0.39818(11) 0.0456(8) Uani 1 1 d . . . . .
C15 C 0.2679(3) 0.4831(4) 0.35724(11) 0.0480(8) Uani 1 1 d . . . . .
H15 H 0.326440 0.590035 0.358800 0.058 Uiso 1 1 calc R U . . .
C6 C 0.2196(3) 0.4235(4) 0.40087(12) 0.0465(8) Uani 1 1 d . . . . .
C3 C 0.2652(3) 0.5204(4) 0.45095(12) 0.0487(8) Uani 1 1 d . . . . .
C11 C 0.0390(3) -0.0408(5) 0.35383(12) 0.0508(8) Uani 1 1 d . . . . .
H11 H 0.038658 -0.129423 0.326233 0.061 Uiso 1 1 calc R U . . .
C10 C -0.0439(3) -0.0735(5) 0.39254(14) 0.0626(10) Uani 1 1 d . . . . .
H10 H -0.098764 -0.184709 0.391093 0.075 Uiso 1 1 calc R U . . .
C4 C 0.2888(4) 0.7211(5) 0.45427(14) 0.0609(9) Uani 1 1 d . . . . .
H4 H 0.267124 0.801607 0.425415 0.073 Uiso 1 1 calc R U . . .
C9 C -0.0456(4) 0.0572(6) 0.43302(15) 0.0711(11) Uani 1 1 d . . . . .
H9 H -0.103681 0.037135 0.458361 0.085 Uiso 1 1 calc R U . . .
C8 C 0.0384(3) 0.2180(5) 0.43621(13) 0.0616(10) Uani 1 1 d . . . . .
H8 H 0.037403 0.305082 0.464073 0.074 Uiso 1 1 calc R U . . .
C5 C 0.3445(4) 0.8017(6) 0.50030(18) 0.0789(12) Uani 1 1 d . . . . .
H5 H 0.362268 0.936741 0.500751 0.095 Uiso 1 1 calc R U . . .
C2 C 0.2956(4) 0.4167(6) 0.49684(13) 0.0679(10) Uani 1 1 d . . . . .
H2 H 0.279018 0.281476 0.497728 0.082 Uiso 1 1 calc R U . . .
C1 C 0.3503(5) 0.5117(7) 0.54119(15) 0.0862(13) Uani 1 1 d . . . . .
H1 H 0.371227 0.436383 0.571092 0.103 Uiso 1 1 calc R U . . .
C21 C 0.3503(3) -0.0822(4) 0.27954(11) 0.0404(7) Uani 1 1 d . . . . .
C16 C 0.3428(3) 0.0471(4) 0.32074(10) 0.0376(7) Uani 1 1 d . . . . .
C17 C 0.4468(3) 0.0564(4) 0.35945(12) 0.0468(8) Uani 1 1 d . . . . .
H17 H 0.443390 0.142120 0.387465 0.056 Uiso 1 1 calc R U . . .
C22 C 0.1514(3) 0.0778(4) 0.26033(11) 0.0444(7) Uani 1 1 d . . . . .
C20 C 0.4581(3) -0.2046(5) 0.27558(13) 0.0519(8) Uani 1 1 d . . . . .
H20 H 0.460885 -0.291385 0.247754 0.062 Uiso 1 1 calc R U . . .
C18 C 0.5575(3) -0.0646(5) 0.35611(13) 0.0564(9) Uani 1 1 d . . . . .
H18 H 0.629038 -0.058843 0.382007 0.068 Uiso 1 1 calc R U . . .
C19 C 0.5625(3) -0.1925(5) 0.31502(14) 0.0568(9) Uani 1 1 d . . . . .
H19 H 0.637288 -0.272605 0.313608 0.068 Uiso 1 1 calc R U . . .
N2 N 0.2353(2) -0.0626(4) 0.24435(9) 0.0455(7) Uani 1 1 d . . . . .
O1 O 0.0474(2) 0.1308(3) 0.23649(9) 0.0586(7) Uani 1 1 d . . . . .
C23 C 0.2096(4) -0.1715(5) 0.19584(13) 0.0638(10) Uani 1 1 d . . . . .
H23A H 0.128334 -0.124349 0.177071 0.096 Uiso 1 1 calc R U . . .
H23B H 0.200934 -0.309799 0.203252 0.096 Uiso 1 1 calc R U . . .
H23C H 0.282656 -0.152246 0.175118 0.096 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
N1 C1 1.316(6) . ?
N1 C5 1.312(5) . ?
C13 C16 1.507(4) . ?
C13 C12 1.530(4) . ?
C13 C22 1.534(4) . ?
C13 C14 1.540(4) . ?
C12 C11 1.383(4) . ?
C12 C7 1.404(4) . ?
C14 C15 1.483(4) . ?
C7 C8 1.403(4) . ?
C7 C6 1.485(4) . ?
C15 C6 1.333(4) . ?
C6 C3 1.479(4) . ?
C3 C4 1.378(5) . ?
C3 C2 1.383(4) . ?
C11 C10 1.383(4) . ?
C10 C9 1.370(5) . ?
C4 C5 1.372(5) . ?
C9 C8 1.373(5) . ?
C2 C1 1.376(5) . ?
C21 C20 1.375(4) . ?
C21 C16 1.384(4) . ?
C21 N2 1.400(4) . ?
C16 C17 1.370(4) . ?
C17 C18 1.390(4) . ?
C22 O1 1.210(3) . ?
C22 N2 1.361(4) . ?
C20 C19 1.386(5) . ?
C18 C19 1.373(4) . ?
N2 C23 1.452(4) . ?

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
C1 N1 C5 115.6(4) . . ?
C16 C13 C12 112.8(2) . . ?
C16 C13 C22 101.6(2) . . ?
C12 C13 C22 111.2(2) . . ?
C16 C13 C14 113.8(2) . . ?
C12 C13 C14 109.3(2) . . ?
C22 C13 C14 107.8(2) . . ?
C11 C12 C7 119.8(3) . . ?
C11 C12 C13 120.8(3) . . ?
C7 C12 C13 119.4(2) . . ?
C15 C14 C13 111.5(2) . . ?
C12 C7 C8 118.1(3) . . ?
C12 C7 C6 119.3(2) . . ?
C8 C7 C6 122.6(3) . . ?
C6 C15 C14 122.4(3) . . ?
C15 C6 C3 119.8(3) . . ?
C15 C6 C7 118.6(3) . . ?
C3 C6 C7 121.5(3) . . ?
C4 C3 C2 115.1(3) . . ?
C4 C3 C6 121.8(3) . . ?
C2 C3 C6 123.0(3) . . ?
C10 C11 C12 120.6(3) . . ?
C9 C10 C11 120.2(3) . . ?
C5 C4 C3 119.8(4) . . ?
C10 C9 C8 120.0(3) . . ?
C9 C8 C7 121.2(3) . . ?
N1 C5 C4 125.1(4) . . ?
C1 C2 C3 120.7(4) . . ?
N1 C1 C2 123.7(4) . . ?
C20 C21 C16 122.9(3) . . ?
C20 C21 N2 127.7(3) . . ?
C16 C21 N2 109.4(2) . . ?
C17 C16 C21 119.4(3) . . ?
C17 C16 C13 131.3(2) . . ?
C21 C16 C13 109.3(3) . . ?
C16 C17 C18 118.9(3) . . ?
O1 C22 N2 125.6(3) . . ?
O1 C22 C13 126.1(3) . . ?
N2 C22 C13 108.3(3) . . ?
C21 C20 C19 116.9(3) . . ?
C19 C18 C17 120.7(3) . . ?
C18 C19 C20 121.3(3) . . ?
C22 N2 C21 111.4(2) . . ?
C22 N2 C23 123.6(3) . . ?
C21 N2 C23 125.0(3) . . ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.120

