# 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_240912_nwj_4_78
_database_code_depnum_ccdc_archive 'CCDC 2504276'
loop_
_audit_author_name
_audit_author_address
XHD
;university of south china
China
;
_audit_update_record             
;
2025-11-20 deposited with the CCDC.	2026-03-09 downloaded from the CCDC.
;
_audit_creation_date             2024-09-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 N2 O'
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   10.9912(4)
_cell_length_b                   7.7964(3)
_cell_length_c                   29.0779(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2491.74(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9793
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.654
_cell_measurement_theta_min      2.644
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.428
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1355 before and 0.0563 after correction.
The Ratio of minimum to maximum transmission is 0.8618.
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    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod-like
_exptl_crystal_F_000             1040
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            38346
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.654
_diffrn_reflns_theta_min         4.387
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III M28'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON III'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'liquid Metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_type              'Bruker Excillum Metaljet D2+'
_diffrn_source_voltage           69.91
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2608
_reflns_number_total             2864
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.175
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2864
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+0.7236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1142
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16)
;
_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
O1 O 0.31541(9) 0.19586(18) 0.64981(3) 0.0647(4) Uani 1 1 d . . . . .
N1 N 0.58855(8) 0.38605(11) 0.56709(3) 0.0248(2) Uani 1 1 d . . . . .
N2 N 0.75425(10) 0.57010(15) 0.59800(3) 0.0426(3) Uani 1 1 d . . . . .
C1 C 0.68276(9) 0.41750(13) 0.49163(3) 0.0276(2) Uani 1 1 d . . . . .
H1 H 0.738788 0.496761 0.504563 0.033 Uiso 1 1 calc R U . . .
C2 C 0.68892(10) 0.37659(14) 0.44525(4) 0.0301(2) Uani 1 1 d . . . . .
H2 H 0.749666 0.428023 0.426541 0.036 Uiso 1 1 calc R U . . .
C3 C 0.60754(10) 0.26163(14) 0.42588(4) 0.0307(2) Uani 1 1 d . . . . .
H3 H 0.612769 0.233065 0.394180 0.037 Uiso 1 1 calc R U . . .
C4 C 0.51855(11) 0.18903(15) 0.45335(4) 0.0323(2) Uani 1 1 d . . . . .
H4 H 0.461562 0.111620 0.440213 0.039 Uiso 1 1 calc R U . . .
C5 C 0.51151(10) 0.22802(14) 0.49998(4) 0.0298(2) Uani 1 1 d . . . . .
H5 H 0.450415 0.176870 0.518583 0.036 Uiso 1 1 calc R U . . .
C6 C 0.59401(9) 0.34177(12) 0.51914(3) 0.0232(2) Uani 1 1 d . . . . .
C7 C 0.67752(10) 0.48511(14) 0.58412(3) 0.0287(2) Uani 1 1 d . . . . .
C8 C 0.50035(9) 0.32504(14) 0.59756(3) 0.0282(2) Uani 1 1 d . . . . .
H8 H 0.438077 0.254837 0.584954 0.034 Uiso 1 1 calc R U . . .
C9 C 0.49511(10) 0.35561(14) 0.64240(4) 0.0285(2) Uani 1 1 d . . . . .
H9 H 0.554501 0.425389 0.657006 0.034 Uiso 1 1 calc R U . . .
C10 C 0.39475(10) 0.27855(16) 0.66902(4) 0.0321(3) Uani 1 1 d . . . . .
C11 C 0.39286(9) 0.29532(13) 0.72019(3) 0.0265(2) Uani 1 1 d . . . . .
C12 C 0.48614(10) 0.37263(14) 0.74496(4) 0.0313(2) Uani 1 1 d . . . . .
H12 H 0.552286 0.424344 0.729148 0.038 Uiso 1 1 calc R U . . .
C13 C 0.48304(12) 0.37459(16) 0.79277(4) 0.0366(3) Uani 1 1 d . . . . .
H13 H 0.547625 0.425912 0.809566 0.044 Uiso 1 1 calc R U . . .
C14 C 0.38583(11) 0.30174(15) 0.81586(4) 0.0356(3) Uani 1 1 d . . . . .
H14 H 0.383565 0.303899 0.848517 0.043 Uiso 1 1 calc R U . . .
C15 C 0.29179(11) 0.22567(15) 0.79156(4) 0.0348(3) Uani 1 1 d . . . . .
H15 H 0.225003 0.176323 0.807530 0.042 Uiso 1 1 calc R U . . .
C16 C 0.29522(10) 0.22161(15) 0.74389(4) 0.0317(2) Uani 1 1 d . . . . .
H16 H 0.231014 0.168565 0.727269 0.038 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 C10 1.2198(14) . ?
N1 C6 1.4378(12) . ?
N1 C7 1.3407(13) . ?
N1 C8 1.3968(13) . ?
N2 C7 1.1460(15) . ?
C1 H1 0.9500 . ?
C1 C2 1.3876(14) . ?
C1 C6 1.3927(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.3859(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3839(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3917(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3853(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.3267(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.4754(14) . ?
C10 C11 1.4938(14) . ?
C11 C12 1.3903(15) . ?
C11 C16 1.3989(14) . ?
C12 H12 0.9500 . ?
C12 C13 1.3908(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.3839(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3855(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3870(16) . ?
C16 H16 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
C7 N1 C6 117.77(8) . . ?
C7 N1 C8 117.91(8) . . ?
C8 N1 C6 124.22(9) . . ?
C2 C1 H1 120.2 . . ?
C2 C1 C6 119.66(10) . . ?
C6 C1 H1 120.2 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.81(10) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.08(10) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.82(10) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.68(10) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 N1 118.97(9) . . ?
C5 C6 N1 121.09(9) . . ?
C5 C6 C1 119.93(9) . . ?
N2 C7 N1 178.94(11) . . ?
N1 C8 H8 116.8 . . ?
C9 C8 N1 126.32(10) . . ?
C9 C8 H8 116.8 . . ?
C8 C9 H9 120.8 . . ?
C8 C9 C10 118.35(10) . . ?
C10 C9 H9 120.8 . . ?
O1 C10 C9 120.62(10) . . ?
O1 C10 C11 119.50(10) . . ?
C9 C10 C11 119.82(9) . . ?
C12 C11 C10 122.93(9) . . ?
C12 C11 C16 119.25(10) . . ?
C16 C11 C10 117.73(9) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.30(10) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.96(11) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.28(10) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.95(10) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.25(10) . . ?
C15 C16 H16 119.9 . . ?


_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_olex2_submission_special_instructions 'No special instructions were received'
