# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2491238'
loop_
_audit_author_name
_audit_author_address
'Huan Cong'
;Technical Institute of Physics and Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2025-09-24 deposited with the CCDC.	2026-01-07 downloaded from the CCDC.
;
_audit_creation_date             2024-07-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 N2 O'
_chemical_formula_sum            'C17 H16 N2 O'
_chemical_formula_weight         264.32
_chemical_absolute_configuration ad
_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   4.6491(13)
_cell_length_b                   12.775(3)
_cell_length_c                   22.835(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1356.3(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9732
_cell_measurement_temperature    130.00
_cell_measurement_theta_max      57.359
_cell_measurement_theta_min      3.368
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6216
_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 0.0619 after correction.
The Ratio of minimum to maximum transmission is 0.8275.
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    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            22137
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.932
_diffrn_reflns_theta_min         3.368
_diffrn_ambient_temperature      130.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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             0.19977099999999998
_diffrn_source_voltage           69.85
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                2700
_reflns_number_total             2797
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 1073 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2797
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.055
_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)+(0.0328P)²+0.2594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0705
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C4(H4), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_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 -0.0922(3) 0.31315(8) 0.30505(5) 0.0254(3) Uani 1 1 d . . . . .
N1 N 0.4938(3) 0.61852(10) 0.35415(5) 0.0218(3) Uani 1 1 d . . . . .
N2 N 0.1084(3) 0.28890(10) 0.21574(6) 0.0269(3) Uani 1 1 d . . . . .
C1 C -0.0762(4) 0.25742(12) 0.25377(7) 0.0276(3) Uani 1 1 d . . . . .
H1A H -0.195693 0.198433 0.246724 0.033 Uiso 1 1 calc R U . . .
C2 C 0.2355(3) 0.37695(11) 0.24279(7) 0.0211(3) Uani 1 1 d . . . . .
C3 C 0.4480(4) 0.44687(11) 0.22427(6) 0.0222(3) Uani 1 1 d . . . . .
H3 H 0.534722 0.440418 0.186769 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5277(3) 0.52568(11) 0.26238(6) 0.0202(3) Uani 1 1 d . . . . .
H4 H 0.671876 0.573876 0.250492 0.024 Uiso 1 1 calc R U . . .
C5 C 0.1132(3) 0.39028(11) 0.29760(6) 0.0204(3) Uani 1 1 d . . . . .
C6 C 0.1878(3) 0.46730(11) 0.33717(6) 0.0210(3) Uani 1 1 d . . . . .
H6 H 0.099639 0.472528 0.374590 0.025 Uiso 1 1 calc R U . . .
C7 C 0.4016(3) 0.53733(11) 0.31880(6) 0.0184(3) Uani 1 1 d . . . . .
C8 C 0.3297(4) 0.65314(11) 0.40518(6) 0.0220(3) Uani 1 1 d . . . . .
H8 H 0.120419 0.646022 0.395927 0.026 Uiso 1 1 calc R U . . .
C9 C 0.3939(5) 0.76901(12) 0.41604(7) 0.0313(4) Uani 1 1 d . . . . .
H9A H 0.601966 0.778946 0.420179 0.047 Uiso 1 1 calc R U . . .
H9B H 0.297268 0.791775 0.451986 0.047 Uiso 1 1 calc R U . . .
H9C H 0.323689 0.810524 0.382902 0.047 Uiso 1 1 calc R U . . .
C10 C 0.3919(4) 0.59026(11) 0.45980(6) 0.0228(3) Uani 1 1 d . . . . .
H10 H 0.278150 0.605020 0.493359 0.027 Uiso 1 1 calc R U . . .
C11 C 0.5907(4) 0.51634(11) 0.46521(6) 0.0227(3) Uani 1 1 d . . . . .
H11 H 0.697764 0.500008 0.430976 0.027 Uiso 1 1 calc R U . . .
C12 C 0.6638(3) 0.45671(11) 0.51849(6) 0.0223(3) Uani 1 1 d . . . . .
C13 C 0.5324(4) 0.47506(12) 0.57276(6) 0.0253(3) Uani 1 1 d . . . . .
H13 H 0.389973 0.528058 0.576082 0.030 Uiso 1 1 calc R U . . .
C14 C 0.6076(4) 0.41683(13) 0.62168(7) 0.0290(4) Uani 1 1 d . . . . .
H14 H 0.516366 0.430176 0.658146 0.035 Uiso 1 1 calc R U . . .
C15 C 0.8154(4) 0.33915(13) 0.61766(7) 0.0299(4) Uani 1 1 d . . . . .
H15 H 0.866632 0.299497 0.651278 0.036 Uiso 1 1 calc R U . . .
C16 C 0.9478(4) 0.31970(13) 0.56445(8) 0.0320(4) Uani 1 1 d . . . . .
H16 H 1.089768 0.266507 0.561407 0.038 Uiso 1 1 calc R U . . .
C17 C 0.8721(4) 0.37838(13) 0.51536(7) 0.0276(3) Uani 1 1 d . . . . .
H17 H 0.964340 0.364728 0.479026 0.033 Uiso 1 1 calc R U . . .
H1 H 0.604(5) 0.6636(15) 0.3377(8) 0.034(5) Uiso 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
O1 C1 1.3725(19) . ?
O1 C5 1.3828(19) . ?
N1 C7 1.3825(19) . ?
N1 C8 1.4611(19) . ?
N1 H1 0.86(2) . ?
N2 C1 1.285(2) . ?
N2 C2 1.4128(19) . ?
C1 H1A 0.9500 . ?
C2 C3 1.398(2) . ?
C2 C5 1.385(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(2) . ?
C4 H4 0.9500 . ?
C4 C7 1.4229(19) . ?
C5 C6 1.380(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.402(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.530(2) . ?
C8 C10 1.511(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.327(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.475(2) . ?
C12 C13 1.401(2) . ?
C12 C17 1.394(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.394(2) . ?
C17 H17 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
C1 O1 C5 103.12(12) . . ?
C7 N1 C8 122.08(13) . . ?
C7 N1 H1 115.6(13) . . ?
C8 N1 H1 117.3(13) . . ?
C1 N2 C2 103.46(13) . . ?
O1 C1 H1A 121.6 . . ?
N2 C1 O1 116.77(14) . . ?
N2 C1 H1A 121.6 . . ?
C3 C2 N2 132.23(14) . . ?
C5 C2 N2 108.75(14) . . ?
C5 C2 C3 119.02(14) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 C2 117.68(14) . . ?
C4 C3 H3 121.2 . . ?
C3 C4 H4 118.8 . . ?
C3 C4 C7 122.43(14) . . ?
C7 C4 H4 118.8 . . ?
O1 C5 C2 107.89(13) . . ?
C6 C5 O1 126.94(13) . . ?
C6 C5 C2 125.18(14) . . ?
C5 C6 H6 122.0 . . ?
C5 C6 C7 115.93(13) . . ?
C7 C6 H6 122.0 . . ?
N1 C7 C4 118.66(14) . . ?
N1 C7 C6 121.58(13) . . ?
C6 C7 C4 119.75(13) . . ?
N1 C8 H8 108.2 . . ?
N1 C8 C9 108.68(13) . . ?
N1 C8 C10 113.42(13) . . ?
C9 C8 H8 108.2 . . ?
C10 C8 H8 108.2 . . ?
C10 C8 C9 110.07(12) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10 117.0 . . ?
C11 C10 C8 126.03(14) . . ?
C11 C10 H10 117.0 . . ?
C10 C11 H11 116.4 . . ?
C10 C11 C12 127.22(14) . . ?
C12 C11 H11 116.4 . . ?
C13 C12 C11 122.84(14) . . ?
C17 C12 C11 119.23(14) . . ?
C17 C12 C13 117.92(14) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.83(15) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.39(15) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.71(15) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.83(16) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 H17 119.3 . . ?
C16 C17 C12 121.33(15) . . ?
C16 C17 H17 119.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
