# 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. 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 2375576'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;Yunnan University
China
;
_audit_update_record             
;
2024-08-05 deposited with the CCDC.	2024-11-12 downloaded from the CCDC.
;
_audit_creation_date             2024-01-18
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2024,
https://github.com/dkratzert/FinalCif
;
_diffrn_source_power             0.07
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C18 H15 N O'
_chemical_formula_moiety         'C18 H15 N O'
_chemical_formula_weight         261.31
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_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), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_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.
;

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'
'-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                   9.5331(3)
_cell_length_b                   11.0505(3)
_cell_length_c                   26.8472(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2828.23(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    298.00
_cell_measurement_reflns_used    6102
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      26.87
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7047
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0906 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.9450.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.986
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      298.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            33019
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_theta_min         2.621
_diffrn_reflns_theta_max         28.336
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3523
_reflns_number_gt                2100
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+0.5898P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3523
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.1545
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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 0.3066(2) 0.35857(15) 0.66108(7) 0.0922(6) Uani 1 1 d . . . . .
N1 N 0.30337(16) 0.57075(14) 0.51682(6) 0.0511(4) Uani 1 1 d . . . . .
C1 C 0.4442(2) 0.53212(18) 0.67209(7) 0.0522(5) Uani 1 1 d . . . . .
C2 C 0.4264(2) 0.65641(19) 0.67430(7) 0.0575(5) Uani 1 1 d . . . . .
H2 H 0.357666 0.693440 0.655029 0.069 Uiso 1 1 calc R U . . .
C3 C 0.5103(3) 0.7253(2) 0.70491(8) 0.0728(7) Uani 1 1 d . . . . .
H3 H 0.497189 0.808559 0.706574 0.087 Uiso 1 1 calc R U . . .
C4 C 0.6134(3) 0.6715(3) 0.73305(9) 0.0836(8) Uani 1 1 d . . . . .
H4 H 0.669966 0.718497 0.753614 0.100 Uiso 1 1 calc R U . . .
C5 C 0.6328(3) 0.5491(3) 0.73083(9) 0.0829(8) Uani 1 1 d . . . . .
H5 H 0.703345 0.513009 0.749619 0.100 Uiso 1 1 calc R U . . .
C6 C 0.5484(2) 0.4789(2) 0.70086(8) 0.0687(6) Uani 1 1 d . . . . .
H6 H 0.561229 0.395535 0.699872 0.082 Uiso 1 1 calc R U . . .
C7 C 0.3482(2) 0.45365(19) 0.64269(8) 0.0588(5) Uani 1 1 d . . . . .
C8 C 0.30614(19) 0.48770(17) 0.59255(7) 0.0524(5) Uani 1 1 d . . . . .
C9 C 0.36534(19) 0.57499(17) 0.56249(7) 0.0493(5) Uani 1 1 d . . . . .
H9 H 0.436151 0.628188 0.571885 0.059 Uiso 1 1 calc R U . . .
C10 C 0.2032(2) 0.4798(2) 0.51754(9) 0.0637(6) Uani 1 1 d . . . . .
H10 H 0.145139 0.458257 0.491144 0.076 Uiso 1 1 calc R U . . .
C11 C 0.2041(2) 0.42795(19) 0.56286(9) 0.0637(6) Uani 1 1 d . . . . .
H11 H 0.147572 0.363943 0.573022 0.076 Uiso 1 1 calc R U . . .
C12 C 0.33463(19) 0.64939(18) 0.47607(7) 0.0510(5) Uani 1 1 d . . . . .
C13 C 0.2320(2) 0.6823(2) 0.44233(8) 0.0688(6) Uani 1 1 d . . . . .
H13 H 0.141594 0.651625 0.445452 0.083 Uiso 1 1 calc R U . . .
C14 C 0.2641(3) 0.7606(2) 0.40402(8) 0.0767(7) Uani 1 1 d . . . . .
H14 H 0.194290 0.781808 0.381461 0.092 Uiso 1 1 calc R U . . .
C15 C 0.3972(2) 0.8087(2) 0.39812(8) 0.0639(6) Uani 1 1 d . . . . .
C16 C 0.4978(2) 0.7736(2) 0.43190(7) 0.0591(5) Uani 1 1 d . . . . .
H16 H 0.588294 0.804081 0.428752 0.071 Uiso 1 1 calc R U . . .
C17 C 0.4684(2) 0.69457(18) 0.47034(7) 0.0532(5) Uani 1 1 d . . . . .
H17 H 0.538920 0.671809 0.492369 0.064 Uiso 1 1 calc R U . . .
C18 C 0.4319(3) 0.8952(3) 0.35665(9) 0.0947(9) Uani 1 1 d . . . . .
H18A H 0.401483 0.861682 0.325485 0.142 Uiso 1 1 calc R U . . .
H18B H 0.531389 0.908389 0.355689 0.142 Uiso 1 1 calc R U . . .
H18C H 0.384914 0.970830 0.362318 0.142 Uiso 1 1 calc R U . . .


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 C7 1.227(2) . ?
N1 C9 1.362(2) . ?
N1 C10 1.387(2) . ?
N1 C12 1.429(3) . ?
C1 C2 1.385(3) . ?
C1 C6 1.389(3) . ?
C1 C7 1.487(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.454(3) . ?
C8 C9 1.379(3) . ?
C8 C11 1.421(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.345(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(3) . ?
C12 C17 1.378(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(3) . ?
C15 C16 1.375(3) . ?
C15 C18 1.504(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C9 N1 C10 108.13(18) . . ?
C9 N1 C12 125.32(16) . . ?
C10 N1 C12 126.53(17) . . ?
C2 C1 C6 118.9(2) . . ?
C2 C1 C7 121.72(19) . . ?
C6 C1 C7 119.2(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 H6 119.8 . . ?
O1 C7 C1 119.0(2) . . ?
O1 C7 C8 120.3(2) . . ?
C8 C7 C1 120.68(18) . . ?
C9 C8 C7 127.59(18) . . ?
C9 C8 C11 106.09(18) . . ?
C11 C8 C7 126.03(19) . . ?
N1 C9 C8 108.99(17) . . ?
N1 C9 H9 125.5 . . ?
C8 C9 H9 125.5 . . ?
N1 C10 H10 125.8 . . ?
C11 C10 N1 108.48(18) . . ?
C11 C10 H10 125.8 . . ?
C8 C11 H11 125.8 . . ?
C10 C11 C8 108.31(19) . . ?
C10 C11 H11 125.8 . . ?
C13 C12 N1 120.95(18) . . ?
C17 C12 N1 119.92(17) . . ?
C17 C12 C13 119.1(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.0 . . ?
C13 C14 C15 122.0(2) . . ?
C15 C14 H14 119.0 . . ?
C14 C15 C18 122.0(2) . . ?
C16 C15 C14 117.1(2) . . ?
C16 C15 C18 120.9(2) . . ?
C15 C16 H16 119.0 . . ?
C15 C16 C17 122.0(2) . . ?
C17 C16 H16 119.0 . . ?
C12 C17 C16 120.01(19) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
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 C7 C8 C9 -164.6(2) . . . . ?
O1 C7 C8 C11 8.3(3) . . . . ?
N1 C10 C11 C8 0.8(2) . . . . ?
N1 C12 C13 C14 178.43(19) . . . . ?
N1 C12 C17 C16 -177.94(17) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C7 C8 C9 14.3(3) . . . . ?
C1 C7 C8 C11 -172.76(18) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C2 C1 C7 O1 -136.3(2) . . . . ?
C2 C1 C7 C8 44.8(3) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C6 C1 C7 O1 39.2(3) . . . . ?
C6 C1 C7 C8 -139.7(2) . . . . ?
C7 C1 C2 C3 174.92(19) . . . . ?
C7 C1 C6 C5 -175.9(2) . . . . ?
C7 C8 C9 N1 174.43(19) . . . . ?
C7 C8 C11 C10 -174.9(2) . . . . ?
C9 N1 C10 C11 -0.5(2) . . . . ?
C9 N1 C12 C13 -147.6(2) . . . . ?
C9 N1 C12 C17 31.7(3) . . . . ?
C9 C8 C11 C10 -0.7(2) . . . . ?
C10 N1 C9 C8 0.0(2) . . . . ?
C10 N1 C12 C13 30.5(3) . . . . ?
C10 N1 C12 C17 -150.24(19) . . . . ?
C11 C8 C9 N1 0.4(2) . . . . ?
C12 N1 C9 C8 178.41(16) . . . . ?
C12 N1 C10 C11 -178.85(18) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C13 C12 C17 C16 1.4(3) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C13 C14 C15 C18 -179.3(2) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C12 -0.7(3) . . . . ?
C17 C12 C13 C14 -0.9(3) . . . . ?
C18 C15 C16 C17 179.8(2) . . . . ?

