# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
# 
#######################################################################

data_a_a
_database_code_depnum_ccdc_archive 'CCDC 2516944'
loop_
_audit_author_name
_audit_author_address
'Shuyi Li'
;Inner Mongolia University of Technology
China
;
_audit_update_record             
;
2025-12-18 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2025-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H14 N2 O'
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_formula_weight         237.27
_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 0.0033 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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   10.114(3)
_cell_length_b                   17.036(5)
_cell_length_c                   7.5282(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.445(4)
_cell_angle_gamma                90.00
_cell_volume                     1230.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2287
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.39
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.1004 before and 0.0498 after correction. The Ratio of minimum to maximum transmission is 0.8985. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7117
_diffrn_reflns_theta_full        27.29
_diffrn_reflns_theta_max         27.29
_diffrn_reflns_theta_min         2.39
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2006
_reflns_number_total             2742
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2742
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0684
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1158P)²+0.5656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2004
_refine_ls_wR_factor_ref         0.2214
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C4(H4), C5(H5), C2(H2), C11(H11), C3(H3), C8(H8), C9(H9),
 C10(H10)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.36460(19) 0.46667(14) 0.1083(3) 0.0657(6) Uani 1 d . . . .
N1 N 0.5955(2) 0.44185(13) 0.2014(3) 0.0503(6) Uani 1 d . . . .
H1 H 0.6020 0.4646 0.1025 0.060 Uiso 1 calc . . R .
N2 N 0.7110(2) 0.37784(15) 0.4880(3) 0.0546(6) Uani 1 d . . . .
C1 C 0.8390(2) 0.35928(15) 0.6320(3) 0.0425(6) Uani 1 d . . . .
C7 C 0.5849(2) 0.36835(14) 0.5222(3) 0.0408(5) Uani 1 d . . . .
C12 C 0.4628(2) 0.39588(13) 0.3915(3) 0.0412(5) Uani 1 d . . . .
C13 C 0.4692(2) 0.43771(14) 0.2220(3) 0.0442(6) Uani 1 d . . . .
C6 C 0.9102(3) 0.29180(16) 0.6213(3) 0.0490(6) Uani 1 d . . . .
H6 H 0.8721 0.2557 0.5262 0.059 Uiso 1 calc . . R .
C4 C 1.0967(2) 0.33032(17) 0.8925(3) 0.0504(6) Uani 1 d . . . .
H4 H 1.1849 0.3217 0.9773 0.060 Uiso 1 calc . . R .
C5 C 1.0397(3) 0.27764(17) 0.7530(3) 0.0531(7) Uani 1 d . . . .
H5 H 1.0877 0.2318 0.7459 0.064 Uiso 1 calc . . R .
C2 C 0.8934(3) 0.41063(17) 0.7776(4) 0.0602(8) Uani 1 d . . . .
H2 H 0.8432 0.4550 0.7893 0.072 Uiso 1 calc . . R .
C11 C 0.3363(3) 0.38577(18) 0.4210(4) 0.0581(7) Uani 1 d . . . .
H11 H 0.2556 0.4040 0.3322 0.070 Uiso 1 calc . . R .
C3 C 1.0227(3) 0.39625(18) 0.9066(4) 0.0609(8) Uani 1 d . . . .
H3 H 1.0599 0.4316 1.0039 0.073 Uiso 1 calc . . R .
C8 C 0.5747(3) 0.33057(18) 0.6825(4) 0.0586(7) Uani 1 d . . . .
H8 H 0.6545 0.3111 0.7709 0.070 Uiso 1 calc . . R .
C9 C 0.4476(3) 0.32196(19) 0.7101(4) 0.0622(8) Uani 1 d . . . .
H9 H 0.4426 0.2975 0.8182 0.075 Uiso 1 calc . . R .
C10 C 0.3273(3) 0.3491(2) 0.5798(4) 0.0634(8) Uani 1 d . . . .
H10 H 0.2414 0.3428 0.5988 0.076 Uiso 1 calc . . R .
C15 C 0.8433(3) 0.4267(2) 0.2854(5) 0.0762(10) Uani 1 d . . . .
H15A H 0.8377 0.4021 0.1685 0.114 Uiso 1 calc . . GR .
H15B H 0.9210 0.4055 0.3829 0.114 Uiso 1 calc . . GR .
H15C H 0.8554 0.4822 0.2760 0.114 Uiso 1 calc . . GR .
C14 C 0.7180(4) 0.4120(4) 0.3283(6) 0.124(2) Uani 1 d . . . U

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0454(10) 0.0923(15) 0.0514(11) 0.0315(10) 0.0039(8) 0.0050(10)
N1 0.0460(12) 0.0676(14) 0.0351(10) 0.0194(9) 0.0099(9) 0.0018(10)
N2 0.0392(11) 0.0862(16) 0.0367(11) 0.0229(10) 0.0098(9) 0.0058(10)
C1 0.0378(11) 0.0567(14) 0.0323(11) 0.0101(9) 0.0099(9) 0.0015(10)
C7 0.0430(12) 0.0425(12) 0.0360(11) 0.0036(9) 0.0114(9) 0.0000(9)
C12 0.0412(12) 0.0426(12) 0.0376(11) 0.0049(9) 0.0094(9) -0.0027(9)
C13 0.0414(12) 0.0495(13) 0.0362(11) 0.0059(10) 0.0043(10) -0.0014(10)
C6 0.0497(14) 0.0579(15) 0.0359(12) -0.0020(10) 0.0088(10) 0.0016(11)
C4 0.0357(12) 0.0731(17) 0.0389(12) 0.0111(12) 0.0070(10) -0.0019(11)
C5 0.0505(14) 0.0667(16) 0.0426(13) 0.0043(11) 0.0155(11) 0.0165(12)
C2 0.0703(18) 0.0536(15) 0.0458(14) 0.0010(12) 0.0029(13) 0.0142(13)
C11 0.0409(13) 0.0726(18) 0.0578(16) 0.0173(13) 0.0113(12) -0.0010(12)
C3 0.0680(18) 0.0564(16) 0.0442(14) -0.0018(12) -0.0024(13) -0.0054(13)
C8 0.0534(15) 0.0768(19) 0.0443(14) 0.0233(13) 0.0138(12) 0.0050(13)
C9 0.0608(17) 0.0755(19) 0.0544(15) 0.0216(14) 0.0242(13) -0.0024(14)
C10 0.0506(15) 0.081(2) 0.0636(17) 0.0141(15) 0.0249(13) -0.0078(13)
C15 0.0511(16) 0.118(3) 0.0640(19) 0.0405(19) 0.0242(14) 0.0090(17)
C14 0.0514(18) 0.229(5) 0.096(3) 0.115(3) 0.0285(18) 0.031(2)

_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 C13 1.234(3) . ?
N1 C13 1.337(3) . ?
N1 C14 1.399(4) . ?
N2 C1 1.436(3) . ?
N2 C7 1.389(3) . ?
N2 C14 1.358(4) . ?
C1 C6 1.373(4) . ?
C1 C2 1.374(4) . ?
C7 C12 1.394(3) . ?
C7 C8 1.400(3) . ?
C12 C13 1.481(3) . ?
C12 C11 1.376(4) . ?
C6 C5 1.391(3) . ?
C4 C5 1.363(4) . ?
C4 C3 1.372(4) . ?
C2 C3 1.382(4) . ?
C11 C10 1.377(4) . ?
C8 C9 1.373(4) . ?
C9 C10 1.379(4) . ?
C15 C14 1.425(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
C13 N1 C14 125.1(2) . . ?
C7 N2 C1 119.72(19) . . ?
C14 N2 C1 118.4(2) . . ?
C14 N2 C7 121.5(2) . . ?
C6 C1 N2 120.3(2) . . ?
C6 C1 C2 119.6(2) . . ?
C2 C1 N2 120.0(2) . . ?
N2 C7 C12 119.4(2) . . ?
N2 C7 C8 122.4(2) . . ?
C12 C7 C8 118.2(2) . . ?
C7 C12 C13 120.0(2) . . ?
C11 C12 C7 120.3(2) . . ?
C11 C12 C13 119.7(2) . . ?
O1 C13 N1 122.7(2) . . ?
O1 C13 C12 121.9(2) . . ?
N1 C13 C12 115.44(19) . . ?
C1 C6 C5 119.8(2) . . ?
C5 C4 C3 119.4(2) . . ?
C4 C5 C6 120.6(2) . . ?
C1 C2 C3 119.9(3) . . ?
C12 C11 C10 121.1(2) . . ?
C4 C3 C2 120.6(3) . . ?
C9 C8 C7 120.5(2) . . ?
C8 C9 C10 120.9(2) . . ?
C11 C10 C9 118.9(2) . . ?
N1 C14 C15 116.2(3) . . ?
N2 C14 N1 118.5(3) . . ?
N2 C14 C15 125.1(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
