# 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_apqt2_0m
_database_code_depnum_ccdc_archive 'CCDC 2414626'
loop_
_audit_author_name
_audit_author_address
'Nguyen Hung Huy'
;Hanoi University of Science
Vietnam
;
_audit_update_record             
;
2025-01-05 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_audit_creation_date             2025-01-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H15 N3 O2'
_chemical_formula_sum            'C23 H15 N3 O2'
_chemical_formula_weight         365.38
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.3695(2)
_cell_length_b                   7.37850(10)
_cell_length_c                   18.8523(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.7020(10)
_cell_angle_gamma                90
_cell_volume                     1718.71(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7990
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      65.034
_cell_measurement_theta_min      4.372
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1182 before and 0.0732 after correction.
The Ratio of minimum to maximum transmission is 0.8921.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22227
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        65.046
_diffrn_reflns_theta_max         65.046
_diffrn_reflns_theta_min         4.186
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2075
_reflns_number_total             2932
_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 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      1.122
_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)+(0.0304P)²+2.4829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1506
_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:
 C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
;
_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 0.6782(2) 0.2824(4) 0.63737(14) 0.0440(7) Uani 1 1 d . . . . .
C2 C 0.7883(2) 0.2900(5) 0.62773(15) 0.0498(8) Uani 1 1 d . . . . .
H2 H 0.842058 0.280535 0.663714 0.060 Uiso 1 1 calc R U . . .
C3 C 0.8064(2) 0.3138(5) 0.55610(15) 0.0490(8) Uani 1 1 d . . . . .
H3 H 0.873339 0.323748 0.535973 0.059 Uiso 1 1 calc R U . . .
C4 C 0.7058(2) 0.3199(4) 0.52023(14) 0.0405(7) Uani 1 1 d . . . . .
C5 C 0.6709(2) 0.3480(4) 0.44778(14) 0.0412(7) Uani 1 1 d . . . . .
C6 C 0.4964(2) 0.2675(4) 0.47323(15) 0.0417(7) Uani 1 1 d . . . . .
C7 C 0.3926(2) 0.2197(4) 0.44670(17) 0.0501(8) Uani 1 1 d . . . . .
H7 H 0.374324 0.235966 0.398714 0.060 Uiso 1 1 calc R U . . .
C8 C 0.3173(2) 0.1490(4) 0.49040(18) 0.0528(8) Uani 1 1 d . . . . .
H8 H 0.248552 0.118391 0.472171 0.063 Uiso 1 1 calc R U . . .
C9 C 0.3448(2) 0.1238(4) 0.56200(17) 0.0498(8) Uani 1 1 d . . . . .
H9 H 0.294457 0.073960 0.591498 0.060 Uiso 1 1 calc R U . . .
C10 C 0.4451(2) 0.1714(4) 0.58969(16) 0.0451(7) Uani 1 1 d . . . . .
H10 H 0.462487 0.153108 0.637690 0.054 Uiso 1 1 calc R U . . .
C11 C 0.5216(2) 0.2472(4) 0.54620(15) 0.0399(6) Uani 1 1 d . . . . .
C12 C 0.7495(2) 0.4059(4) 0.39504(14) 0.0438(7) Uani 1 1 d . . . . .
C13 C 0.8327(2) 0.5284(4) 0.41118(17) 0.0511(8) Uani 1 1 d . . . . .
H13 H 0.842163 0.574585 0.456948 0.061 Uiso 1 1 calc R U . . .
C14 C 0.9012(3) 0.5813(5) 0.35902(19) 0.0596(9) Uani 1 1 d . . . . .
H14 H 0.956176 0.664177 0.370011 0.072 Uiso 1 1 calc R U . . .
C15 C 0.8893(3) 0.5133(5) 0.29125(19) 0.0617(10) Uani 1 1 d . . . . .
H15 H 0.936619 0.548217 0.256864 0.074 Uiso 1 1 calc R U . . .
C16 C 0.8071(3) 0.3935(6) 0.27466(17) 0.0634(10) Uani 1 1 d . . . . .
H16 H 0.798202 0.347959 0.228760 0.076 Uiso 1 1 calc R U . . .
C17 C 0.7374(3) 0.3402(5) 0.32607(16) 0.0542(8) Uani 1 1 d . . . . .
H17 H 0.681687 0.259444 0.314275 0.065 Uiso 1 1 calc R U . . .
C18 C 0.6267(2) 0.3009(4) 0.70579(15) 0.0439(7) Uani 1 1 d . . . . .
C19 C 0.5411(2) 0.4203(4) 0.71424(15) 0.0459(7) Uani 1 1 d . . . . .
H19 H 0.512176 0.484096 0.675252 0.055 Uiso 1 1 calc R U . . .
C20 C 0.4987(2) 0.4450(4) 0.78040(15) 0.0482(7) Uani 1 1 d . . . . .
H20 H 0.440974 0.523668 0.786079 0.058 Uiso 1 1 calc R U . . .
C21 C 0.5438(2) 0.3501(4) 0.83769(14) 0.0433(7) Uani 1 1 d . . . . .
C22 C 0.6304(2) 0.2341(5) 0.83093(15) 0.0497(8) Uani 1 1 d . . . . .
H22 H 0.660602 0.173624 0.870346 0.060 Uiso 1 1 calc R U . . .
C23 C 0.6711(2) 0.2095(5) 0.76507(15) 0.0493(8) Uani 1 1 d . . . . .
H23 H 0.729009 0.130963 0.759935 0.059 Uiso 1 1 calc R U . . .
N1 N 0.62733(17) 0.2941(3) 0.57036(12) 0.0404(6) Uani 1 1 d . . . . .
N2 N 0.57032(19) 0.3269(3) 0.42524(12) 0.0452(6) Uani 1 1 d . . . . .
N3 N 0.4957(2) 0.3679(4) 0.90687(13) 0.0524(7) Uani 1 1 d . . . . .
O1 O 0.4171(2) 0.4682(4) 0.91168(13) 0.0766(8) Uani 1 1 d . . . . .
O2 O 0.5339(2) 0.2778(4) 0.95650(12) 0.0732(8) 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 C2 1.384(4) . ?
C1 C18 1.471(4) . ?
C1 N1 1.387(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(4) . ?
C4 C5 1.428(4) . ?
C4 N1 1.400(3) . ?
C5 C12 1.486(4) . ?
C5 N2 1.305(4) . ?
C6 C7 1.401(4) . ?
C6 C11 1.404(4) . ?
C6 N2 1.387(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.375(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.389(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.369(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.397(4) . ?
C11 N1 1.408(3) . ?
C12 C13 1.392(4) . ?
C12 C17 1.389(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.372(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.393(4) . ?
C18 C23 1.395(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(4) . ?
C21 C22 1.381(4) . ?
C21 N3 1.465(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.374(4) . ?
C23 H23 0.9300 . ?
N3 O1 1.228(3) . ?
N3 O2 1.225(3) . ?

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 C18 125.5(3) . . ?
C2 C1 N1 106.5(2) . . ?
N1 C1 C18 126.6(2) . . ?
C1 C2 H2 125.1 . . ?
C1 C2 C3 109.7(3) . . ?
C3 C2 H2 125.1 . . ?
C2 C3 H3 126.4 . . ?
C4 C3 C2 107.2(3) . . ?
C4 C3 H3 126.4 . . ?
C3 C4 C5 134.0(3) . . ?
C3 C4 N1 107.5(2) . . ?
N1 C4 C5 118.5(2) . . ?
C4 C5 C12 120.3(2) . . ?
N2 C5 C4 122.3(2) . . ?
N2 C5 C12 117.4(2) . . ?
C7 C6 C11 118.7(3) . . ?
N2 C6 C7 117.9(3) . . ?
N2 C6 C11 123.4(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.3(3) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 N1 116.8(2) . . ?
C10 C11 C6 119.5(3) . . ?
C10 C11 N1 123.6(3) . . ?
C13 C12 C5 122.7(3) . . ?
C17 C12 C5 118.7(3) . . ?
C17 C12 C13 118.5(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.0(3) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C1 121.4(3) . . ?
C19 C18 C23 119.1(3) . . ?
C23 C18 C1 119.2(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.7 . . ?
C21 C20 C19 118.7(3) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 N3 118.9(3) . . ?
C22 C21 C20 121.9(3) . . ?
C22 C21 N3 119.1(3) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 119.0(3) . . ?
C23 C22 H22 120.5 . . ?
C18 C23 H23 119.6 . . ?
C22 C23 C18 120.9(3) . . ?
C22 C23 H23 119.6 . . ?
C1 N1 C4 108.9(2) . . ?
C1 N1 C11 130.8(2) . . ?
C4 N1 C11 118.6(2) . . ?
C5 N2 C6 118.2(2) . . ?
O1 N3 C21 118.4(3) . . ?
O2 N3 C21 118.3(3) . . ?
O2 N3 O1 123.3(3) . . ?

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 -0.4(4) . . . . ?
C1 C18 C19 C20 -175.5(3) . . . . ?
C1 C18 C23 C22 175.1(3) . . . . ?
C2 C1 C18 C19 129.9(3) . . . . ?
C2 C1 C18 C23 -44.1(5) . . . . ?
C2 C1 N1 C4 -3.6(3) . . . . ?
C2 C1 N1 C11 161.2(3) . . . . ?
C2 C3 C4 C5 177.2(3) . . . . ?
C2 C3 C4 N1 -1.8(4) . . . . ?
C3 C4 C5 C12 -9.1(5) . . . . ?
C3 C4 C5 N2 171.9(3) . . . . ?
C3 C4 N1 C1 3.4(3) . . . . ?
C3 C4 N1 C11 -163.6(3) . . . . ?
C4 C5 C12 C13 -37.8(4) . . . . ?
C4 C5 C12 C17 144.5(3) . . . . ?
C4 C5 N2 C6 -2.9(4) . . . . ?
C5 C4 N1 C1 -175.8(3) . . . . ?
C5 C4 N1 C11 17.2(4) . . . . ?
C5 C12 C13 C14 -178.0(3) . . . . ?
C5 C12 C17 C16 178.5(3) . . . . ?
C6 C7 C8 C9 -0.3(5) . . . . ?
C6 C11 N1 C1 -176.8(3) . . . . ?
C6 C11 N1 C4 -13.3(4) . . . . ?
C7 C6 C11 C10 3.4(4) . . . . ?
C7 C6 C11 N1 179.0(3) . . . . ?
C7 C6 N2 C5 -170.8(3) . . . . ?
C7 C8 C9 C10 1.2(5) . . . . ?
C8 C9 C10 C11 0.3(5) . . . . ?
C9 C10 C11 C6 -2.6(4) . . . . ?
C9 C10 C11 N1 -177.9(3) . . . . ?
C10 C11 N1 C1 -1.5(5) . . . . ?
C10 C11 N1 C4 162.1(3) . . . . ?
C11 C6 C7 C8 -2.0(5) . . . . ?
C11 C6 N2 C5 6.9(4) . . . . ?
C12 C5 N2 C6 178.1(3) . . . . ?
C12 C13 C14 C15 -0.7(5) . . . . ?
C13 C12 C17 C16 0.8(5) . . . . ?
C13 C14 C15 C16 1.1(5) . . . . ?
C14 C15 C16 C17 -0.6(5) . . . . ?
C15 C16 C17 C12 -0.3(5) . . . . ?
C17 C12 C13 C14 -0.3(5) . . . . ?
C18 C1 C2 C3 -164.9(3) . . . . ?
C18 C1 N1 C4 163.6(3) . . . . ?
C18 C1 N1 C11 -31.6(5) . . . . ?
C18 C19 C20 C21 0.7(5) . . . . ?
C19 C18 C23 C22 1.0(5) . . . . ?
C19 C20 C21 C22 0.8(5) . . . . ?
C19 C20 C21 N3 -176.7(3) . . . . ?
C20 C21 C22 C23 -1.4(5) . . . . ?
C20 C21 N3 O1 -0.6(4) . . . . ?
C20 C21 N3 O2 177.2(3) . . . . ?
C21 C22 C23 C18 0.5(5) . . . . ?
C22 C21 N3 O1 -178.3(3) . . . . ?
C22 C21 N3 O2 -0.4(4) . . . . ?
C23 C18 C19 C20 -1.6(5) . . . . ?
N1 C1 C2 C3 2.5(4) . . . . ?
N1 C1 C18 C19 -35.0(5) . . . . ?
N1 C1 C18 C23 151.0(3) . . . . ?
N1 C4 C5 C12 169.9(3) . . . . ?
N1 C4 C5 N2 -9.2(4) . . . . ?
N2 C5 C12 C13 141.3(3) . . . . ?
N2 C5 C12 C17 -36.3(4) . . . . ?
N2 C6 C7 C8 175.9(3) . . . . ?
N2 C6 C11 C10 -174.3(3) . . . . ?
N2 C6 C11 N1 1.2(4) . . . . ?
N3 C21 C22 C23 176.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
