# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_compound1
_database_code_depnum_ccdc_archive 'CCDC 2386231'
loop_
_audit_author_name
_audit_author_address
'Wei Zhang'
;Zhongshan Institute for Drug Discovery
China
;
_audit_update_record             
;
2024-09-24 deposited with the CCDC.	2025-02-24 downloaded from the CCDC.
;
_audit_creation_date             2024-09-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_name_systematic        compound1
_chemical_formula_moiety         'C15 H13 N O2'
_chemical_formula_sum            'C15 H13 N O2'
_chemical_formula_weight         239.276
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01370 0.00670 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H -0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.02410 0.01340 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.03890 0.02410 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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

_symmetry_Int_Tables_number      14
_cell_length_a                   8.8108(2)
_cell_length_b                   9.98924(19)
_cell_length_c                   13.7937(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.041(2)
_cell_angle_gamma                90
_cell_volume                     1207.29(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9289
_cell_measurement_temperature    297.99(10)
_cell_measurement_theta_max      56.4090
_cell_measurement_theta_min      3.8550
_exptl_absorpt_coefficient_mu    0.451
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.116a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             505.230
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.9995
_diffrn_reflns_Laue_measured_fraction_max 0.9834
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13864
_diffrn_reflns_point_group_measured_fraction_full 0.9995
_diffrn_reflns_point_group_measured_fraction_max 0.9834
_diffrn_reflns_theta_full        53.5427
_diffrn_reflns_theta_max         56.35
_diffrn_reflns_theta_min         4.76
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9834
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00  74.00   0.50    0.05    --   67.87  77.00 -90.00   52
  2  ω     39.00  65.00   0.50    0.05    --   67.87  77.00 -60.00   52
  3  ω    -46.00 -21.00   0.50    0.05    --  -68.81 125.00 -60.00   50
  4  ω   -110.00 -70.00   0.50    0.05    --  -68.81 125.00 -60.00   80
  5  ω   -111.00 -26.00   0.50    0.05    --  -68.81 125.00-150.00  170
  6  ω     43.00  89.00   0.50    0.05    --   67.87  69.00 -24.20   92
  7  ω     41.00  50.00   0.50    0.05    --   67.87  77.00 -30.00   18
  8  ω     45.00  84.00   0.50    0.05    --   67.87  57.00 -30.00   78
  9  ω     45.00 142.00   0.50    0.05    --   67.87  57.00  30.00  194
 10  ω     76.00 141.00   0.50    0.05    --   67.87  57.00   0.00  130
 11  ω     45.00  95.00   0.50    0.05    --   67.87  57.00 -60.00  100
 12  ω    117.00 142.00   0.50    0.05    --   67.87  57.00 -30.00   50
 13  ω    117.00 142.00   0.50    0.05    --   67.87  77.00 -60.00   50
 14  ω    118.00 145.00   0.50    0.05    --   67.87  25.00-145.00   54
 15  ω     -5.00  49.00   0.50    0.05    --   67.87 -57.00 -60.00  108
 16  ω     -4.00  70.00   0.50    0.05    --   67.87 -25.00  51.00  148
 17  ω     31.00  71.00   0.50    0.05    --   -0.47  25.00-145.00   80
 18  ω    -60.00 -12.00   0.50    0.05    --  -68.81  25.00-145.00   96
 19  ω    -63.00   6.00   0.50    0.05    --  -68.81  38.00  30.00  138
 20  ω     12.00  37.00   0.50    0.05    --   -0.47 -99.00   0.00   50
 21  ω      1.00  35.00   0.50    0.05    --   -0.47 -99.00 -60.00   68
 22  ω      0.00  25.00   0.50    0.05    --   -0.47 -99.00-150.00   50
 23  ω     -7.00  33.00   0.50    0.05    --   -0.47 -99.00  60.00   80
 24  ω   -137.00 -87.00   0.50    0.05    --  -68.81-125.00 150.00  100
 25  ω    -75.00 -41.00   0.50    0.05    --  -68.81 -77.00 -30.00   68
 26  ω   -135.00 -46.00   0.50    0.05    --  -68.81 -43.00 -87.16  178
 27  ω   -119.00 -94.00   0.50    0.05    --  -68.81 -25.00  51.00   50
 28  ω    -68.00 -27.00   0.50    0.05    --   -0.47 -25.00  51.00   82
 29  ω     -7.00  19.00   0.50    0.05    --   -0.47 -25.00  51.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.34050
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2110
_reflns_number_total             2376
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.116a 64-bit (release 22-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.2390
_refine_diff_density_min         -0.4114
_refine_diff_density_rms         0.1072
_refine_ls_d_res_high            0.8051
_refine_ls_d_res_low             8.0750
_refine_ls_goodness_of_fit_ref   1.0616
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.0616
_refine_ls_shift/su_max          -0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0812P)²+0.1137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1228
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O 0.41248(10) 0.32301(8) 0.72608(6) 0.0411(2) Uani 1.000000 .
O2 O 0.46401(10) 0.52553(8) 0.65215(6) 0.0426(3) Uani 1.000000 .
H2 H 0.4480(14) 0.5710(9) 0.6995(7) 0.0638(4) Uiso 1.000000 GR
N2 N 0.52096(11) 0.23122(10) 0.69540(7) 0.0392(3) Uani 1.000000 .
C C 0.36719(13) 0.41425(11) 0.64600(8) 0.0344(3) Uani 1.000000 .
C1 C 0.20113(13) 0.44978(12) 0.65068(8) 0.0367(3) Uani 1.000000 .
C2 C 0.51844(12) 0.23746(11) 0.60227(8) 0.0337(3) Uani 1.000000 .
C3 C 0.61573(13) 0.15136(11) 0.54883(8) 0.0349(3) Uani 1.000000 .
C4 C 0.59229(14) 0.14562(12) 0.44770(9) 0.0391(3) Uani 1.000000 .
H4 H 0.51677(14) 0.19800(12) 0.41423(9) 0.0470(4) Uiso 1.000000 R
C5 C 0.40293(13) 0.33480(11) 0.55715(8) 0.0347(3) Uani 1.000000 .
H5a H 0.31306(13) 0.28949(11) 0.52640(8) 0.0416(3) Uiso 1.000000 R
H5b H 0.44531(13) 0.39146(11) 0.50963(8) 0.0416(3) Uiso 1.000000 R
C6 C 0.72970(15) 0.07250(13) 0.59781(10) 0.0451(3) Uani 1.000000 .
H6 H 0.74725(15) 0.07622(13) 0.66543(10) 0.0541(4) Uiso 1.000000 R
C7 C 0.10120(16) 0.36058(14) 0.68762(11) 0.0497(3) Uani 1.000000 .
H7 H 0.13676(16) 0.27810(14) 0.71165(11) 0.0596(4) Uiso 1.000000 R
C8 C 0.14510(16) 0.57138(13) 0.61420(10) 0.0499(3) Uani 1.000000 .
H8 H 0.21029(16) 0.63215(13) 0.58868(10) 0.0599(4) Uiso 1.000000 R
C9 C 0.68091(15) 0.06223(14) 0.39656(10) 0.0476(3) Uani 1.000000 .
H9 H 0.66498(15) 0.05899(14) 0.32887(10) 0.0571(4) Uiso 1.000000 R
C10 C 0.79241(16) -0.01578(14) 0.44562(11) 0.0529(4) Uani 1.000000 .
H10 H 0.85173(16) -0.07183(14) 0.41116(11) 0.0635(4) Uiso 1.000000 R
C11 C 0.81629(16) -0.01080(14) 0.54639(12) 0.0538(4) Uani 1.000000 .
H11 H 0.89129(16) -0.06409(14) 0.57948(12) 0.0646(4) Uiso 1.000000 R
C12 C -0.00830(19) 0.60269(17) 0.61566(13) 0.0652(5) Uani 1.000000 .
H12 H -0.04506(19) 0.68447(17) 0.59098(13) 0.0783(5) Uiso 1.000000 R
C13 C -0.05146(18) 0.39365(18) 0.68895(13) 0.0641(4) Uani 1.000000 .
H13 H -0.11746(18) 0.33350(18) 0.71436(13) 0.0769(5) Uiso 1.000000 R
C14 C -0.10580(18) 0.5147(2) 0.65296(12) 0.0672(5) Uani 1.000000 .
H14 H -0.20821(18) 0.5366(2) 0.65397(12) 0.0806(6) Uiso 1.000000 R


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 N2 1.4207(12) . ?
O1 C 1.4551(13) . ?
O2 H2 0.8200 . ?
O2 C 1.3984(13) . ?
N2 C2 1.2840(14) . ?
C C1 1.5135(16) . ?
C C5 1.5206(15) . ?
C1 C7 1.3868(17) . ?
C1 C8 1.3857(18) . ?
C2 C3 1.4666(16) . ?
C2 C5 1.4951(15) . ?
C3 C4 1.3897(16) . ?
C3 C6 1.3938(17) . ?
C4 H4 0.9300 . ?
C4 C9 1.3846(18) . ?
C5 H5a 0.9700 . ?
C5 H5b 0.9700 . ?
C6 H6 0.9300 . ?
C6 C11 1.3753(19) . ?
C7 H7 0.9300 . ?
C7 C13 1.387(2) . ?
C8 H8 0.9300 . ?
C8 C12 1.389(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C14 1.367(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(3) . ?
C14 H14 0.9300 . ?

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
C O1 N2 108.51(8) . . ?
C O2 H2 109.5 . . ?
C2 N2 O1 108.99(9) . . ?
O2 C O1 109.58(9) . . ?
C1 C O1 107.67(9) . . ?
C1 C O2 113.41(9) . . ?
C5 C O1 102.79(8) . . ?
C5 C O2 106.68(9) . . ?
C5 C C1 116.10(9) . . ?
C7 C1 C 121.26(11) . . ?
C8 C1 C 119.94(11) . . ?
C8 C1 C7 118.75(12) . . ?
C3 C2 N2 121.66(10) . . ?
C5 C2 N2 112.80(10) . . ?
C5 C2 C3 125.48(10) . . ?
C4 C3 C2 119.72(10) . . ?
C6 C3 C2 121.14(11) . . ?
C6 C3 C4 119.12(11) . . ?
H4 C4 C3 119.87(7) . . ?
C9 C4 C3 120.27(12) . . ?
C9 C4 H4 119.87(8) . . ?
C2 C5 C 101.16(9) . . ?
H5a C5 C 111.54(6) . . ?
H5a C5 C2 111.54(6) . . ?
H5b C5 C 111.54(6) . . ?
H5b C5 C2 111.54(6) . . ?
H5b C5 H5a 109.4 . . ?
H6 C6 C3 119.92(7) . . ?
C11 C6 C3 120.16(13) . . ?
C11 C6 H6 119.92(9) . . ?
H7 C7 C1 119.81(8) . . ?
C13 C7 C1 120.39(14) . . ?
C13 C7 H7 119.81(9) . . ?
H8 C8 C1 119.93(8) . . ?
C12 C8 C1 120.13(14) . . ?
C12 C8 H8 119.93(9) . . ?
H9 C9 C4 119.92(8) . . ?
C10 C9 C4 120.15(13) . . ?
C10 C9 H9 119.92(8) . . ?
H10 C10 C9 120.04(8) . . ?
C11 C10 C9 119.93(12) . . ?
C11 C10 H10 120.04(8) . . ?
C10 C11 C6 120.37(13) . . ?
H11 C11 C6 119.82(9) . . ?
H11 C11 C10 119.82(8) . . ?
H12 C12 C8 119.62(9) . . ?
C14 C12 C8 120.76(15) . . ?
C14 C12 H12 119.62(9) . . ?
H13 C13 C7 119.79(9) . . ?
C14 C13 C7 120.43(15) . . ?
C14 C13 H13 119.79(10) . . ?
C13 C14 C12 119.54(14) . . ?
H14 C14 C12 120.23(9) . . ?
H14 C14 C13 120.23(10) . . ?

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 N2 C2 C3 -178.39(8) . . . . ?
O1 N2 C2 C5 -1.13(10) . . . . ?
O1 C C1 C7 -30.05(11) . . . . ?
O1 C C1 C8 152.45(9) . . . . ?
O1 C C5 C2 -22.09(9) . . . . ?
O2 C C1 C7 -151.46(10) . . . . ?
O2 C C1 C8 31.03(12) . . . . ?
O2 C C5 C2 93.17(9) . . . . ?
N2 C2 C3 C4 169.64(11) . . . . ?
N2 C2 C3 C6 -8.93(13) . . . . ?
N2 C2 C5 C 15.22(10) . . . . ?
C C1 C7 C13 -178.31(13) . . . . ?
C C1 C8 C12 178.05(12) . . . . ?
C C5 C2 C3 -167.64(8) . . . . ?
C1 C7 C13 C14 0.53(17) . . . . ?
C1 C8 C12 C14 0.07(17) . . . . ?
C2 C3 C4 C9 -178.41(11) . . . . ?
C2 C3 C6 C11 177.86(12) . . . . ?
C3 C4 C9 C10 0.21(14) . . . . ?
C3 C6 C11 C10 0.85(15) . . . . ?
C4 C9 C10 C11 -0.09(15) . . . . ?
C6 C11 C10 C9 -0.44(16) . . . . ?
C7 C13 C14 C12 0.03(19) . . . . ?
C8 C12 C14 C13 -0.32(19) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
