# 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 
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# Please retain this information to preserve the provenance of 
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data_mj24678_0m
_database_code_depnum_ccdc_archive 'CCDC 2372228'
loop_
_audit_author_name
_audit_author_address
XiaoZhangone
;Changzhou University
China
;
_audit_update_record             
;
2024-07-20 deposited with the CCDC.	2025-11-27 downloaded from the CCDC.
;
_audit_creation_date             2024-07-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 N3 O2'
_chemical_formula_sum            'C18 H17 N3 O2'
_chemical_formula_weight         307.34
_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      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                   6.8712(2)
_cell_length_b                   24.6723(7)
_cell_length_c                   9.0721(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.358(2)
_cell_angle_gamma                90
_cell_volume                     1537.55(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7448
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.892
_cell_measurement_theta_min      4.521
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.457
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1670 before and 0.0803 after correction.
The Ratio of minimum to maximum transmission is 0.7583.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14979
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.868
_diffrn_reflns_theta_min         4.519
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2309
_reflns_number_total             2899
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0704P)²+0.2876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1300
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), 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
O1 O 0.9124(2) 0.60002(6) 0.99246(15) 0.0509(4) Uani 1 1 d . . . . .
O2 O 0.8821(2) 0.66201(5) 0.82410(16) 0.0498(4) Uani 1 1 d . . . . .
N1 N 0.71290(19) 0.35864(5) 0.47021(14) 0.0278(3) Uani 1 1 d . . . . .
N2 N 0.73060(17) 0.44943(5) 0.46307(13) 0.0236(3) Uani 1 1 d . . . . .
N3 N 0.8828(2) 0.61402(6) 0.86332(17) 0.0377(4) Uani 1 1 d . . . . .
C1 C 0.7492(2) 0.40450(6) 0.55520(16) 0.0248(3) Uani 1 1 d . . . . .
C2 C 0.7990(2) 0.42114(7) 0.69616(16) 0.0282(4) Uani 1 1 d . . . . .
H2 H 0.822364 0.398834 0.780087 0.034 Uiso 1 1 calc R U . . .
C3 C 0.8082(2) 0.47901(6) 0.68965(16) 0.0255(3) Uani 1 1 d . . . . .
C4 C 0.8496(2) 0.51874(7) 0.79594(17) 0.0285(4) Uani 1 1 d . . . . .
H4 H 0.880370 0.509152 0.895203 0.034 Uiso 1 1 calc R U . . .
C5 C 0.8445(2) 0.57219(7) 0.75205(18) 0.0300(4) Uani 1 1 d . . . . .
C6 C 0.8028(2) 0.58897(7) 0.60764(19) 0.0303(4) Uani 1 1 d . . . . .
H6 H 0.802409 0.626418 0.583251 0.036 Uiso 1 1 calc R U . . .
C7 C 0.7620(2) 0.55033(6) 0.50041(18) 0.0279(4) Uani 1 1 d . . . . .
H7 H 0.733240 0.560532 0.401297 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7647(2) 0.49630(6) 0.54248(16) 0.0241(3) Uani 1 1 d . . . . .
C9 C 0.6822(2) 0.43295(6) 0.32011(15) 0.0232(3) Uani 1 1 d . . . . .
C10 C 0.6690(2) 0.37618(6) 0.32509(16) 0.0253(3) Uani 1 1 d . . . . .
C11 C 0.6187(2) 0.34789(7) 0.19694(16) 0.0302(4) Uani 1 1 d . . . . .
H11 H 0.607101 0.309526 0.197353 0.036 Uiso 1 1 calc R U . . .
C12 C 0.5861(2) 0.37754(7) 0.06836(17) 0.0316(4) Uani 1 1 d . . . . .
H12 H 0.551246 0.358846 -0.019940 0.038 Uiso 1 1 calc R U . . .
C13 C 0.6028(2) 0.43345(7) 0.06501(16) 0.0303(4) Uani 1 1 d . . . . .
H13 H 0.580400 0.452257 -0.025178 0.036 Uiso 1 1 calc R U . . .
C14 C 0.6518(2) 0.46235(7) 0.19181(16) 0.0270(4) Uani 1 1 d . . . . .
H14 H 0.663843 0.500706 0.190537 0.032 Uiso 1 1 calc R U . . .
C15 C 0.6966(2) 0.30151(6) 0.52289(17) 0.0304(4) Uani 1 1 d . . . . .
C16 C 0.4849(3) 0.28295(7) 0.5049(2) 0.0391(4) Uani 1 1 d . . . . .
H16A H 0.402811 0.304469 0.569581 0.059 Uiso 1 1 calc R U . . .
H16B H 0.475214 0.244555 0.531364 0.059 Uiso 1 1 calc R U . . .
H16C H 0.441179 0.287942 0.402183 0.059 Uiso 1 1 calc R U . . .
C17 C 0.8355(3) 0.26546(7) 0.4366(2) 0.0448(5) Uani 1 1 d . . . . .
H17A H 0.803651 0.268074 0.330991 0.067 Uiso 1 1 calc R U . . .
H17B H 0.821948 0.227764 0.468824 0.067 Uiso 1 1 calc R U . . .
H17C H 0.969875 0.277501 0.454883 0.067 Uiso 1 1 calc R U . . .
C18 C 0.7549(3) 0.29767(7) 0.68540(19) 0.0425(5) Uani 1 1 d . . . . .
H18A H 0.888946 0.310561 0.699700 0.064 Uiso 1 1 calc R U . . .
H18B H 0.746124 0.259884 0.717830 0.064 Uiso 1 1 calc R U . . .
H18C H 0.667261 0.320109 0.743336 0.064 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 N3 1.234(2) . ?
O2 N3 1.236(2) . ?
N1 C1 1.388(2) . ?
N1 C10 1.4118(19) . ?
N1 C15 1.493(2) . ?
N2 C1 1.3924(19) . ?
N2 C8 1.3795(19) . ?
N2 C9 1.3920(19) . ?
N3 C5 1.463(2) . ?
C1 C2 1.378(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.430(2) . ?
C3 C4 1.400(2) . ?
C3 C8 1.427(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(2) . ?
C5 C6 1.397(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(2) . ?
C9 C10 1.404(2) . ?
C9 C14 1.383(2) . ?
C10 C11 1.392(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.530(2) . ?
C15 C17 1.533(2) . ?
C15 C18 1.522(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 C10 107.44(12) . . ?
C1 N1 C15 127.25(13) . . ?
C10 N1 C15 124.87(13) . . ?
C8 N2 C1 109.99(12) . . ?
C8 N2 C9 139.93(13) . . ?
C9 N2 C1 110.07(12) . . ?
O1 N3 O2 122.75(15) . . ?
O1 N3 C5 118.72(15) . . ?
O2 N3 C5 118.53(15) . . ?
N1 C1 N2 107.62(13) . . ?
C2 C1 N1 142.68(14) . . ?
C2 C1 N2 109.69(13) . . ?
C1 C2 H2 127.2 . . ?
C1 C2 C3 105.62(13) . . ?
C3 C2 H2 127.2 . . ?
C4 C3 C2 132.77(14) . . ?
C4 C3 C8 118.04(15) . . ?
C8 C3 C2 109.19(13) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 C3 117.90(15) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 N3 118.22(15) . . ?
C4 C5 C6 123.91(15) . . ?
C6 C5 N3 117.86(15) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.20(15) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 121.1 . . ?
C6 C7 C8 117.84(15) . . ?
C8 C7 H7 121.1 . . ?
N2 C8 C3 105.50(13) . . ?
N2 C8 C7 131.39(14) . . ?
C7 C8 C3 123.11(14) . . ?
N2 C9 C10 106.00(12) . . ?
C14 C9 N2 131.21(15) . . ?
C14 C9 C10 122.79(14) . . ?
C9 C10 N1 108.86(13) . . ?
C11 C10 N1 131.93(15) . . ?
C11 C10 C9 119.21(13) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 C10 117.95(15) . . ?
C12 C11 H11 121.0 . . ?
C11 C12 H12 119.0 . . ?
C13 C12 C11 122.04(15) . . ?
C13 C12 H12 119.0 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.82(14) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 C13 117.18(15) . . ?
C9 C14 H14 121.4 . . ?
C13 C14 H14 121.4 . . ?
N1 C15 C16 109.08(13) . . ?
N1 C15 C17 109.37(13) . . ?
N1 C15 C18 110.40(13) . . ?
C16 C15 C17 111.96(15) . . ?
C18 C15 C16 108.23(14) . . ?
C18 C15 C17 107.79(14) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
O1 N3 C5 C4 -2.1(2) . . . . ?
O1 N3 C5 C6 177.24(14) . . . . ?
O2 N3 C5 C4 178.61(14) . . . . ?
O2 N3 C5 C6 -2.0(2) . . . . ?
N1 C1 C2 C3 179.7(2) . . . . ?
N1 C10 C11 C12 -179.20(15) . . . . ?
N2 C1 C2 C3 0.88(17) . . . . ?
N2 C9 C10 N1 -1.08(16) . . . . ?
N2 C9 C10 C11 178.93(13) . . . . ?
N2 C9 C14 C13 -179.40(14) . . . . ?
N3 C5 C6 C7 -178.71(13) . . . . ?
C1 N1 C10 C9 1.20(16) . . . . ?
C1 N1 C10 C11 -178.82(16) . . . . ?
C1 N1 C15 C16 110.49(17) . . . . ?
C1 N1 C15 C17 -126.75(17) . . . . ?
C1 N1 C15 C18 -8.3(2) . . . . ?
C1 N2 C8 C3 0.63(16) . . . . ?
C1 N2 C8 C7 -179.57(15) . . . . ?
C1 N2 C9 C10 0.58(16) . . . . ?
C1 N2 C9 C14 -178.91(15) . . . . ?
C1 C2 C3 C4 179.50(16) . . . . ?
C1 C2 C3 C8 -0.49(17) . . . . ?
C2 C3 C4 C5 -179.51(16) . . . . ?
C2 C3 C8 N2 -0.08(16) . . . . ?
C2 C3 C8 C7 -179.90(14) . . . . ?
C3 C4 C5 N3 178.45(13) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C3 C8 N2 179.93(12) . . . . ?
C4 C3 C8 C7 0.1(2) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C5 C6 C7 C8 0.0(2) . . . . ?
C6 C7 C8 N2 179.86(14) . . . . ?
C6 C7 C8 C3 -0.4(2) . . . . ?
C8 N2 C1 N1 179.78(11) . . . . ?
C8 N2 C1 C2 -0.97(17) . . . . ?
C8 N2 C9 C10 -178.87(16) . . . . ?
C8 N2 C9 C14 1.6(3) . . . . ?
C8 C3 C4 C5 0.5(2) . . . . ?
C9 N2 C1 N1 0.16(16) . . . . ?
C9 N2 C1 C2 179.41(12) . . . . ?
C9 N2 C8 C3 -179.93(16) . . . . ?
C9 N2 C8 C7 -0.1(3) . . . . ?
C9 C10 C11 C12 0.8(2) . . . . ?
C10 N1 C1 N2 -0.82(16) . . . . ?
C10 N1 C1 C2 -179.7(2) . . . . ?
C10 N1 C15 C16 -60.96(19) . . . . ?
C10 N1 C15 C17 61.79(19) . . . . ?
C10 N1 C15 C18 -179.77(14) . . . . ?
C10 C9 C14 C13 1.2(2) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
C11 C12 C13 C14 -0.5(2) . . . . ?
C12 C13 C14 C9 -0.2(2) . . . . ?
C14 C9 C10 N1 178.45(13) . . . . ?
C14 C9 C10 C11 -1.5(2) . . . . ?
C15 N1 C1 N2 -173.48(13) . . . . ?
C15 N1 C1 C2 7.7(3) . . . . ?
C15 N1 C10 C9 174.07(13) . . . . ?
C15 N1 C10 C11 -5.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
