# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2311417'
loop_
_audit_author_name
_audit_author_address
'Bao-Gui Cai'
;Anhui University
China
;
_audit_update_record             
;
2023-12-01 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_1_a                 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.943 Why?  
RESPONSE: This is caused as the sample is twinned.
;
_vrf_PLAT082_1_a                 
;
PROBLEM: High R1 Value ..................................       0.16 Report
RESPONSE: This is caused by the poor quality of the sample.
;
_vrf_PLAT340_1_a                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02289 Ang.  
RESPONSE: This is caused by the poor quality of the sample.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 N2 O'
_chemical_formula_weight         274.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   5.8824(19)
_cell_length_b                   8.460(3)
_cell_length_c                   15.027(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.383(19)
_cell_angle_gamma                90
_cell_volume                     747.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2111
_cell_measurement_theta_min      6.00
_cell_measurement_theta_max      56.60

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.609
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5090
_diffrn_reflns_av_unetI/netI     0.1201
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.941
_diffrn_reflns_theta_max         67.051
_diffrn_reflns_theta_full        67.051
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_point_group_measured_fraction_full 0.810
_reflns_number_total             2154
_reflns_number_gt                1301
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.599
_reflns_Friedel_fraction_max     0.655
_reflns_Friedel_fraction_full    0.655

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0100P)²+5.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 310 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         2154
_refine_ls_number_parameters     166
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.2252
_refine_ls_R_factor_gt           0.1644
_refine_ls_wR_factor_ref         0.3503
_refine_ls_wR_factor_gt          0.3332
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.250(2) 0.3531(13) 0.7952(9) 0.100(5) Uani 1 1 d G U . . .
H1 H 0.110783 0.390307 0.814936 0.119 Uiso 1 1 calc R U . . .
C2 C 0.297(2) 0.1921(12) 0.7975(10) 0.111(5) Uani 1 1 d G U . . .
H2 H 0.189511 0.121631 0.818663 0.133 Uiso 1 1 calc R U . . .
C3 C 0.504(3) 0.1366(12) 0.7680(10) 0.110(5) Uani 1 1 d G U . . .
H3 H 0.535765 0.028859 0.769522 0.132 Uiso 1 1 calc R U . . .
C4 C 0.664(2) 0.2420(17) 0.7364(10) 0.110(5) Uani 1 1 d G U . . .
H4 H 0.803295 0.204762 0.716656 0.132 Uiso 1 1 calc R U . . .
C5 C 0.617(2) 0.4029(16) 0.7341(10) 0.103(5) Uani 1 1 d G U . . .
H5 H 0.724572 0.473438 0.712929 0.123 Uiso 1 1 calc R U . . .
C6 C 0.410(2) 0.4585(10) 0.7636(10) 0.091(4) Uani 1 1 d G U . . .
C7 C 0.261(2) 0.6000(14) 0.6014(7) 0.088(4) Uani 1 1 d G U . . .
C8 C 0.4258(18) 0.5818(15) 0.5373(10) 0.097(4) Uani 1 1 d G U . . .
H8 H 0.566904 0.630167 0.544999 0.117 Uiso 1 1 calc R U . . .
C9 C 0.379(2) 0.4914(17) 0.4618(8) 0.099(5) Uani 1 1 d G U . . .
H9 H 0.489542 0.479197 0.418983 0.119 Uiso 1 1 calc R U . . .
C10 C 0.169(3) 0.4191(17) 0.4504(7) 0.100(5) Uani 1 1 d G U . . .
H10 H 0.137531 0.358592 0.399877 0.120 Uiso 1 1 calc R U . . .
C11 C 0.0040(19) 0.4373(16) 0.5144(9) 0.099(5) Uani 1 1 d G U . . .
H11 H -0.137120 0.388953 0.506788 0.119 Uiso 1 1 calc R U . . .
N2 N 0.050(2) 0.5278(15) 0.5899(8) 0.097(4) Uani 1 1 d G U . . .
C13 C 0.347(4) 0.635(2) 0.7532(14) 0.088(3) Uani 1 1 d . U . . .
C14 C 0.259(4) 0.714(2) 0.8387(13) 0.090(4) Uani 1 1 d . U . . .
C15 C 0.399(4) 0.698(3) 0.9143(14) 0.106(5) Uani 1 1 d . U . . .
H15 H 0.528443 0.634980 0.915070 0.127 Uiso 1 1 calc R U . . .
C16 C 0.326(4) 0.788(3) 0.9936(16) 0.112(5) Uani 1 1 d . U . . .
H16 H 0.418799 0.798750 1.044313 0.134 Uiso 1 1 calc R U . . .
C17 C 0.117(4) 0.853(3) 0.9873(16) 0.111(5) Uani 1 1 d . U . . .
H17 H 0.060746 0.895006 1.039625 0.133 Uiso 1 1 calc R U . . .
C18 C -0.022(4) 0.866(3) 0.9125(15) 0.108(5) Uani 1 1 d . U . . .
H18 H -0.156329 0.924201 0.911423 0.130 Uiso 1 1 calc R U . . .
C19 C 0.057(4) 0.782(2) 0.8372(14) 0.093(4) Uani 1 1 d . U . . .
H19 H -0.034716 0.775893 0.786116 0.112 Uiso 1 1 calc R U . . .
N1 N 0.267(3) 0.7002(17) 0.6769(10) 0.081(3) Uani 1 1 d . U . . .
O1 O 0.503(2) 0.7202(14) 0.7056(8) 0.088(3) Uani 1 1 d . 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
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 H1 0.9300 . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C13 1.54(2) . ?
C7 C8 1.3900 . ?
C7 N2 1.3900 . ?
C7 N1 1.416(17) . ?
C8 C9 1.3900 . ?
C8 H8 0.9300 . ?
C9 C10 1.3900 . ?
C9 H9 0.9300 . ?
C10 C11 1.3900 . ?
C10 H10 0.9300 . ?
C11 N2 1.3900 . ?
C11 H11 0.9300 . ?
C13 N1 1.35(2) . ?
C13 O1 1.38(2) . ?
C13 C14 1.55(3) . ?
C14 C19 1.32(3) . ?
C14 C15 1.39(3) . ?
C15 C16 1.49(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.35(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.38(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.42(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N1 O1 1.455(19) . ?

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
C2 C1 C6 120.0 . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C13 120.2(11) . . ?
C1 C6 C13 119.5(11) . . ?
C8 C7 N2 120.0 . . ?
C8 C7 N1 128.1(11) . . ?
N2 C7 N1 111.5(11) . . ?
C7 C8 C9 120.0 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
N2 C11 C10 120.0 . . ?
N2 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 N2 C7 120.0 . . ?
N1 C13 O1 64.4(12) . . ?
N1 C13 C6 124.2(17) . . ?
O1 C13 C6 113.5(15) . . ?
N1 C13 C14 114.0(18) . . ?
O1 C13 C14 116.3(15) . . ?
C6 C13 C14 114.8(17) . . ?
C19 C14 C15 125(2) . . ?
C19 C14 C13 120(2) . . ?
C15 C14 C13 115(2) . . ?
C14 C15 C16 115(2) . . ?
C14 C15 H15 122.4 . . ?
C16 C15 H15 122.4 . . ?
C17 C16 C15 116(2) . . ?
C17 C16 H16 122.2 . . ?
C15 C16 H16 122.2 . . ?
C16 C17 C18 128(2) . . ?
C16 C17 H17 116.1 . . ?
C18 C17 H17 116.1 . . ?
C17 C18 C19 114(2) . . ?
C17 C18 H18 122.9 . . ?
C19 C18 H18 122.9 . . ?
C14 C19 C18 121(2) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C13 N1 C7 115.8(15) . . ?
C13 N1 O1 58.9(12) . . ?
C7 N1 O1 108.1(12) . . ?
C13 O1 N1 56.7(11) . . ?

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
C6 C1 C2 C3 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 C13 -174.3(17) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C6 C13 174.3(16) . . . . ?
N2 C7 C8 C9 0.0 . . . . ?
N1 C7 C8 C9 -172.4(15) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 N2 0.0 . . . . ?
C10 C11 N2 C7 0.0 . . . . ?
C8 C7 N2 C11 0.0 . . . . ?
N1 C7 N2 C11 173.6(12) . . . . ?
C5 C6 C13 N1 80(2) . . . . ?
C1 C6 C13 N1 -94(2) . . . . ?
C5 C6 C13 O1 6(2) . . . . ?
C1 C6 C13 O1 -168.2(13) . . . . ?
C5 C6 C13 C14 -131.0(15) . . . . ?
C1 C6 C13 C14 55(2) . . . . ?
N1 C13 C14 C19 29(3) . . . . ?
O1 C13 C14 C19 101(2) . . . . ?
C6 C13 C14 C19 -123(2) . . . . ?
N1 C13 C14 C15 -154.8(19) . . . . ?
O1 C13 C14 C15 -83(2) . . . . ?
C6 C13 C14 C15 53(2) . . . . ?
C19 C14 C15 C16 -10(3) . . . . ?
C13 C14 C15 C16 173.8(17) . . . . ?
C14 C15 C16 C17 10(3) . . . . ?
C15 C16 C17 C18 -10(4) . . . . ?
C16 C17 C18 C19 8(4) . . . . ?
C15 C14 C19 C18 9(3) . . . . ?
C13 C14 C19 C18 -175.4(18) . . . . ?
C17 C18 C19 C14 -7(3) . . . . ?
O1 C13 N1 C7 96.4(14) . . . . ?
C6 C13 N1 C7 -6(3) . . . . ?
C14 C13 N1 C7 -154.7(15) . . . . ?
C6 C13 N1 O1 -102(2) . . . . ?
C14 C13 N1 O1 108.9(17) . . . . ?
C8 C7 N1 C13 -93.1(17) . . . . ?
N2 C7 N1 C13 94.0(15) . . . . ?
C8 C7 N1 O1 -29.6(17) . . . . ?
N2 C7 N1 O1 157.5(9) . . . . ?
C6 C13 O1 N1 118.1(19) . . . . ?
C14 C13 O1 N1 -105(2) . . . . ?
C7 N1 O1 C13 -109.7(16) . . . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.097



