# 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
_database_code_depnum_ccdc_archive 'CCDC 2293468'
loop_
_audit_author_name
_audit_author_address
'XUN TIAN'
;Yunnan university
China
;
_audit_update_record             
;
2023-09-07 deposited with the CCDC.	2025-01-20 downloaded from the CCDC.
;
_audit_creation_date             2023-09-07
_diffrn_source_power             0.05500000000000001
_audit_creation_method           
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C18 H20 N2 O2'
_chemical_formula_moiety         'C18 H20 N2 O2'
_exptl_crystal_colour_primary    colourless
_chemical_formula_weight         296.36
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C6(H6), C5(H5), C4(H4), C3(H3), C17(H17), C16(H16),
 C15(H15), C14(H14), C18(H18)
2.d Fitted hexagon refined as free rotating group:
 C2(C1,C6,C5,C4,C3), C17(C16,C15,C14,C13,C18)
2.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C  2'
_space_group_name_Hall           'C 2y'
_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   36.827(3)
_cell_length_b                   5.0991(3)
_cell_length_c                   8.2493(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.460(2)
_cell_angle_gamma                90
_cell_volume                     1547.68(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      4.81
_cell_measurement_theta_max      77.37
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5856
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1616 before and 0.0712 after correction.
The Ratio of minimum to maximum transmission is 0.7766.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_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           1.1
_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            25726
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_theta_min         2.402
_diffrn_reflns_theta_max         77.361
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3249
_reflns_number_gt                3192
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_max     0.962
_reflns_Friedel_fraction_full    0.989
_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)+(0.0589P)²+5.1821P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3249
_refine_ls_number_parameters     176
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1604
_refine_ls_wR_factor_gt          0.1600
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.04(16)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1340 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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 0.30848(8) 0.6533(6) 0.6416(4) 0.0233(6) Uani 1 1 d . . . . .
O2 O 0.34196(8) 0.9881(6) 0.2588(4) 0.0237(7) Uani 1 1 d . . . . .
N1 N 0.31427(9) 0.2137(7) 0.6735(4) 0.0201(7) Uani 1 1 d . . . . .
H1 H 0.308133 0.058221 0.634885 0.024 Uiso 1 1 calc R U . . .
N2 N 0.33453(8) 0.5498(6) 0.2844(4) 0.0171(7) Uani 1 1 d . . . . .
H2 H 0.345041 0.394745 0.285685 0.021 Uiso 1 1 calc R U . . .
C2 C 0.39937(7) 0.4021(5) 0.8759(3) 0.0237(9) Uani 1 1 d G . . . .
H2A H 0.389386 0.534846 0.941474 0.028 Uiso 1 1 calc R U . . .
C1 C 0.37665(5) 0.2197(5) 0.7981(3) 0.0205(8) Uani 1 1 d G . . . .
C6 C 0.39126(6) 0.0255(5) 0.7021(3) 0.0228(8) Uani 1 1 d G . . . .
H6 H 0.375731 -0.099225 0.648915 0.027 Uiso 1 1 calc R U . . .
C5 C 0.42857(7) 0.0138(5) 0.6841(3) 0.0254(9) Uani 1 1 d G . . . .
H5 H 0.438554 -0.118877 0.618514 0.030 Uiso 1 1 calc R U . . .
C4 C 0.45129(5) 0.1963(6) 0.7619(4) 0.0267(9) Uani 1 1 d G . . . .
H4 H 0.476793 0.188330 0.749593 0.032 Uiso 1 1 calc R U . . .
C3 C 0.43669(7) 0.3905(5) 0.8579(3) 0.0278(10) Uani 1 1 d G . . . .
H3 H 0.452210 0.515193 0.911073 0.033 Uiso 1 1 calc R U . . .
C7 C 0.33591(11) 0.2275(9) 0.8257(5) 0.0230(8) Uani 1 1 d . . . . .
H7A H 0.329449 0.078519 0.895760 0.028 Uiso 1 1 calc R U . . .
H7B H 0.330045 0.391755 0.882943 0.028 Uiso 1 1 calc R U . . .
C8 C 0.30321(10) 0.4284(8) 0.5891(5) 0.0180(8) Uani 1 1 d . . . . .
C9 C 0.28337(10) 0.3734(8) 0.4297(5) 0.0188(8) Uani 1 1 d . . . . .
H9A H 0.256873 0.389418 0.442971 0.023 Uiso 1 1 calc R U . . .
H9B H 0.288479 0.191337 0.395664 0.023 Uiso 1 1 calc R U . . .
C10 C 0.29503(10) 0.5651(8) 0.2974(5) 0.0188(8) Uani 1 1 d . . . . .
H10 H 0.288542 0.747267 0.330444 0.023 Uiso 1 1 calc R U . . .
C11 C 0.27499(11) 0.5027(10) 0.1359(5) 0.0278(10) Uani 1 1 d . . . . .
H11A H 0.280822 0.636185 0.055538 0.042 Uiso 1 1 calc R U . . .
H11B H 0.248737 0.502056 0.150786 0.042 Uiso 1 1 calc R U . . .
H11C H 0.282573 0.329989 0.097723 0.042 Uiso 1 1 calc R U . . .
C12 C 0.35513(10) 0.7645(7) 0.2708(4) 0.0158(7) Uani 1 1 d . . . . .
C17 C 0.45037(6) 0.5012(4) 0.3643(3) 0.0224(8) Uani 1 1 d G . . . .
H17 H 0.462116 0.364354 0.424555 0.027 Uiso 1 1 calc R U . . .
C16 C 0.47082(5) 0.6788(5) 0.2786(3) 0.0231(9) Uani 1 1 d G . . . .
H16 H 0.496537 0.663277 0.280311 0.028 Uiso 1 1 calc R U . . .
C15 C 0.45363(6) 0.8790(5) 0.1905(3) 0.0222(8) Uani 1 1 d G . . . .
H15 H 0.467607 1.000371 0.131955 0.027 Uiso 1 1 calc R U . . .
C14 C 0.41600(6) 0.9017(5) 0.1881(3) 0.0186(8) Uani 1 1 d G . . . .
H14 H 0.404255 1.038545 0.127840 0.022 Uiso 1 1 calc R U . . .
C13 C 0.39555(5) 0.7241(5) 0.2738(3) 0.0160(7) Uani 1 1 d G . . . .
C18 C 0.41274(6) 0.5239(4) 0.3619(3) 0.0187(8) Uani 1 1 d G . . . .
H18 H 0.398763 0.402528 0.420440 0.022 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 C8 1.238(5) . ?
O2 C12 1.241(5) . ?
N1 H1 0.8800 . ?
N1 C7 1.460(5) . ?
N1 C8 1.351(5) . ?
N2 H2 0.8800 . ?
N2 C10 1.465(5) . ?
N2 C12 1.339(5) . ?
C2 H2A 0.9500 . ?
C2 C1 1.3900 . ?
C2 C3 1.3900 . ?
C1 C6 1.3900 . ?
C1 C7 1.528(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.3900 . ?
C5 H5 0.9500 . ?
C5 C4 1.3900 . ?
C4 H4 0.9500 . ?
C4 C3 1.3900 . ?
C3 H3 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.503(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.540(5) . ?
C10 H10 1.0000 . ?
C10 C11 1.528(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.502(4) . ?
C17 H17 0.9500 . ?
C17 C16 1.3900 . ?
C17 C18 1.3900 . ?
C16 H16 0.9500 . ?
C16 C15 1.3900 . ?
C15 H15 0.9500 . ?
C15 C14 1.3900 . ?
C14 H14 0.9500 . ?
C14 C13 1.3900 . ?
C13 C18 1.3900 . ?
C18 H18 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
C7 N1 H1 118.5 . . ?
C8 N1 H1 118.5 . . ?
C8 N1 C7 123.0(3) . . ?
C10 N2 H2 119.0 . . ?
C12 N2 H2 119.0 . . ?
C12 N2 C10 122.0(3) . . ?
C1 C2 H2A 120.0 . . ?
C1 C2 C3 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C2 C1 C6 120.0 . . ?
C2 C1 C7 119.3(2) . . ?
C6 C1 C7 120.7(2) . . ?
C1 C6 H6 120.0 . . ?
C1 C6 C5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
N1 C7 C1 112.0(3) . . ?
N1 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C1 C7 H7A 109.2 . . ?
C1 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
O1 C8 N1 122.1(4) . . ?
O1 C8 C9 122.8(4) . . ?
N1 C8 C9 115.1(3) . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C8 C9 C10 111.2(3) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
N2 C10 C9 109.0(3) . . ?
N2 C10 H10 108.6 . . ?
N2 C10 C11 111.7(3) . . ?
C9 C10 H10 108.6 . . ?
C11 C10 C9 110.3(3) . . ?
C11 C10 H10 108.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 N2 122.5(3) . . ?
O2 C12 C13 120.7(3) . . ?
N2 C12 C13 116.8(3) . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C14 H14 120.0 . . ?
C15 C14 C13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C13 C12 117.4(2) . . ?
C18 C13 C12 122.5(2) . . ?
C18 C13 C14 120.0 . . ?
C17 C18 H18 120.0 . . ?
C13 C18 C17 120.0 . . ?
C13 C18 H18 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.88 2.07 2.876(4) 152.8 1_545 yes
N2 H2 O2 0.88 2.09 2.886(4) 150.3 1_545 yes

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 C8 C9 C10 42.2(5) . . . . ?
O2 C12 C13 C14 -30.7(4) . . . . ?
O2 C12 C13 C18 147.2(3) . . . . ?
N1 C8 C9 C10 -139.2(3) . . . . ?
N2 C12 C13 C14 150.4(3) . . . . ?
N2 C12 C13 C18 -31.7(4) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C7 N1 132.1(3) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C6 C1 C7 N1 -50.8(4) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C3 C2 C1 C7 177.1(3) . . . . ?
C7 N1 C8 O1 -5.4(6) . . . . ?
C7 N1 C8 C9 176.0(3) . . . . ?
C7 C1 C6 C5 -177.1(3) . . . . ?
C8 N1 C7 C1 -91.2(4) . . . . ?
C8 C9 C10 N2 56.2(4) . . . . ?
C8 C9 C10 C11 179.1(3) . . . . ?
C10 N2 C12 O2 -4.3(6) . . . . ?
C10 N2 C12 C13 174.6(3) . . . . ?
C12 N2 C10 C9 -136.5(4) . . . . ?
C12 N2 C10 C11 101.4(4) . . . . ?
C12 C13 C18 C17 -177.9(3) . . . . ?
C17 C16 C15 C14 0.0 . . . . ?
C16 C17 C18 C13 0.0 . . . . ?
C16 C15 C14 C13 0.0 . . . . ?
C15 C14 C13 C12 178.0(3) . . . . ?
C15 C14 C13 C18 0.0 . . . . ?
C14 C13 C18 C17 0.0 . . . . ?
C18 C17 C16 C15 0.0 . . . . ?

