# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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 
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data_20240725_lyl_0m_pl
_database_code_depnum_ccdc_archive 'CCDC 2449687'
loop_
_audit_author_name
_audit_author_address
'Lei Wang'
;Yangzhou university
China
;
_audit_update_record             
;
2025-05-08 deposited with the CCDC.	2025-07-14 downloaded from the CCDC.
;
_audit_creation_date             2024-07-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 N O2'
_chemical_formula_sum            'C23 H19 N O2'
_chemical_formula_weight         341.39
_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 0.0181 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'

_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      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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.3859(7)
_cell_length_b                   8.7208(3)
_cell_length_c                   11.3513(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.037(2)
_cell_angle_gamma                90
_cell_volume                     1786.40(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4939
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.128
_cell_measurement_theta_min      5.635
_shelx_estimated_absorpt_T_max   0.856
_shelx_estimated_absorpt_T_min   0.807
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1344
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13878
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.590
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_min         5.634
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2410
_reflns_number_total             3139
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0614
_refine_ls_restrained_S_all      1.024
_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)+(0.0976P)²+0.3415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1839
_refine_special_details          ?
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C1(H1), C6(H6), C17(H17), C2(H2), C4(H4), C3(H3), C20(H20),
 C23(H23), C22(H22), C21(H21)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.39457(8) 0.79973(16) 0.11225(14) 0.0609(5) Uani 1 1 d . . . . .
O2 O 0.24598(9) 0.7069(2) -0.00261(13) 0.0664(5) Uani 1 1 d . . . . .
N1 N 0.46638(9) 0.82519(17) 0.09147(14) 0.0493(4) Uani 1 1 d . . . . .
C8 C 0.58915(11) 0.72409(19) 0.13581(16) 0.0464(5) Uani 1 1 d . . . . .
C11 C 0.51036(11) 0.7208(2) 0.14235(16) 0.0468(5) Uani 1 1 d . . . . .
C9 C 0.63870(11) 0.6302(2) 0.20670(17) 0.0484(5) Uani 1 1 d . . . . .
H9 H 0.621336 0.561077 0.259824 0.058 Uiso 1 1 calc R U . . .
C7 C 0.61520(13) 0.8280(2) 0.05622(19) 0.0569(6) Uani 1 1 d . . . . .
H7 H 0.581316 0.894321 0.006885 0.068 Uiso 1 1 calc R U . . .
C13 C 0.39355(12) 0.6597(2) 0.18585(19) 0.0538(5) Uani 1 1 d . . . . .
C16 C 0.26283(13) 0.5924(2) 0.08139(19) 0.0579(6) Uani 1 1 d . . . . .
C1 C 0.76785(13) 0.5379(3) 0.2763(2) 0.0641(6) Uani 1 1 d . . . . .
H1 H 0.751677 0.468656 0.330581 0.077 Uiso 1 1 calc R U . . .
C10 C 0.71543(12) 0.6331(2) 0.20304(17) 0.0503(5) Uani 1 1 d . . . . .
C15 C 0.34148(13) 0.5454(2) 0.1110(2) 0.0602(6) Uani 1 1 d . . . . .
H15A H 0.359112 0.526962 0.035079 0.072 Uiso 1 1 calc R U . . .
H15B H 0.344688 0.446854 0.154976 0.072 Uiso 1 1 calc R U . . .
C6 C 0.68811(14) 0.8324(3) 0.0507(2) 0.0636(6) Uani 1 1 d . . . . .
H6 H 0.704470 0.902081 -0.003058 0.076 Uiso 1 1 calc R U . . .
C5 C 0.74039(13) 0.7367(2) 0.12256(19) 0.0577(6) Uani 1 1 d . . . . .
C17 C 0.20217(15) 0.5467(3) 0.1203(2) 0.0708(7) Uani 1 1 d . . . . .
H17 H 0.199787 0.468661 0.177853 0.085 Uiso 1 1 calc R U . . .
C19 C 0.17096(13) 0.7327(3) -0.0150(2) 0.0638(6) Uani 1 1 d . . . . .
C12 C 0.47358(13) 0.6037(3) 0.2071(2) 0.0714(7) Uani 1 1 d . . . . .
H12A H 0.495675 0.601732 0.293777 0.086 Uiso 1 1 calc R U . . .
H12B H 0.477035 0.500079 0.172974 0.086 Uiso 1 1 calc R U . . .
C14 C 0.36850(15) 0.7077(3) 0.2993(2) 0.0717(7) Uani 1 1 d . . . . .
H14A H 0.403583 0.782374 0.342621 0.108 Uiso 1 1 calc R U . . .
H14B H 0.366444 0.617597 0.350191 0.108 Uiso 1 1 calc R U . . .
H14C H 0.319183 0.754285 0.278938 0.108 Uiso 1 1 calc R U . . .
C18 C 0.14177(14) 0.6365(3) 0.0596(2) 0.0693(7) Uani 1 1 d . . . . .
C2 C 0.84110(14) 0.5439(3) 0.2704(2) 0.0773(7) Uani 1 1 d . . . . .
H2 H 0.875691 0.480142 0.320934 0.093 Uiso 1 1 calc R U . . .
C4 C 0.81702(15) 0.7373(3) 0.1179(2) 0.0752(7) Uani 1 1 d . . . . .
H4 H 0.834686 0.804211 0.063609 0.090 Uiso 1 1 calc R U . . .
C3 C 0.86528(16) 0.6443(4) 0.1894(3) 0.0857(8) Uani 1 1 d . . . . .
H3 H 0.916309 0.647133 0.184794 0.103 Uiso 1 1 calc R U . . .
C20 C 0.13086(17) 0.8382(4) -0.0894(3) 0.0892(9) Uani 1 1 d . . . . .
H20 H 0.153229 0.902384 -0.139999 0.107 Uiso 1 1 calc R U . . .
C23 C 0.06545(17) 0.6479(5) 0.0593(3) 0.0989(10) Uani 1 1 d . . . . .
H23 H 0.042804 0.584101 0.109783 0.119 Uiso 1 1 calc R U . . .
C22 C 0.02470(19) 0.7519(5) -0.0146(4) 0.1108(12) Uani 1 1 d . . . . .
H22 H -0.027025 0.759201 -0.016171 0.133 Uiso 1 1 calc R U . . .
C21 C 0.05652(18) 0.8468(4) -0.0873(3) 0.1040(11) Uani 1 1 d . . . . .
H21 H 0.026583 0.919435 -0.136874 0.125 Uiso 1 1 calc R 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
O1 N1 1.403(2) . ?
O1 C13 1.482(2) . ?
O2 C16 1.375(3) . ?
O2 C19 1.378(3) . ?
N1 C11 1.279(2) . ?
C8 C11 1.465(3) . ?
C8 C9 1.367(3) . ?
C8 C7 1.426(3) . ?
C11 C12 1.494(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.419(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.354(3) . ?
C13 C15 1.524(3) . ?
C13 C12 1.525(3) . ?
C13 C14 1.508(3) . ?
C16 C15 1.478(3) . ?
C16 C17 1.336(3) . ?
C1 H1 0.9500 . ?
C1 C10 1.416(3) . ?
C1 C2 1.362(3) . ?
C10 C5 1.422(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C5 1.409(3) . ?
C5 C4 1.420(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.424(4) . ?
C19 C18 1.373(3) . ?
C19 C20 1.365(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C18 C23 1.406(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.402(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.352(4) . ?
C3 H3 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.374(4) . ?
C23 H23 0.9500 . ?
C23 C22 1.359(5) . ?
C22 H22 0.9500 . ?
C22 C21 1.376(5) . ?
C21 H21 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
N1 O1 C13 109.83(14) . . ?
C16 O2 C19 106.14(17) . . ?
C11 N1 O1 110.21(16) . . ?
C9 C8 C11 120.85(18) . . ?
C9 C8 C7 119.1(2) . . ?
C7 C8 C11 119.99(17) . . ?
N1 C11 C8 120.60(17) . . ?
N1 C11 C12 113.71(19) . . ?
C8 C11 C12 125.68(16) . . ?
C8 C9 H9 119.1 . . ?
C8 C9 C10 121.75(19) . . ?
C10 C9 H9 119.1 . . ?
C8 C7 H7 119.9 . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
O1 C13 C15 107.41(16) . . ?
O1 C13 C12 103.72(17) . . ?
O1 C13 C14 106.98(17) . . ?
C15 C13 C12 111.27(19) . . ?
C14 C13 C15 113.33(19) . . ?
C14 C13 C12 113.4(2) . . ?
O2 C16 C15 116.08(19) . . ?
C17 C16 O2 110.8(2) . . ?
C17 C16 C15 133.2(2) . . ?
C10 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C2 C1 C10 121.1(2) . . ?
C9 C10 C5 118.37(18) . . ?
C1 C10 C9 122.7(2) . . ?
C1 C10 C5 118.9(2) . . ?
C13 C15 H15A 108.4 . . ?
C13 C15 H15B 108.4 . . ?
C16 C15 C13 115.36(17) . . ?
C16 C15 H15A 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.5 . . ?
C7 C6 H6 119.1 . . ?
C7 C6 C5 121.9(2) . . ?
C5 C6 H6 119.1 . . ?
C6 C5 C10 118.7(2) . . ?
C6 C5 C4 123.2(2) . . ?
C4 C5 C10 118.1(2) . . ?
C16 C17 H17 126.3 . . ?
C16 C17 C18 107.4(2) . . ?
C18 C17 H17 126.3 . . ?
C18 C19 O2 109.8(2) . . ?
C20 C19 O2 125.8(2) . . ?
C20 C19 C18 124.4(3) . . ?
C11 C12 C13 102.53(16) . . ?
C11 C12 H12A 111.3 . . ?
C11 C12 H12B 111.3 . . ?
C13 C12 H12A 111.3 . . ?
C13 C12 H12B 111.3 . . ?
H12A C12 H12B 109.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C19 C18 C17 105.9(2) . . ?
C19 C18 C23 117.6(3) . . ?
C23 C18 C17 136.5(3) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C5 C4 H4 119.4 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.4 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C19 C20 H20 121.7 . . ?
C19 C20 C21 116.6(3) . . ?
C21 C20 H20 121.7 . . ?
C18 C23 H23 120.6 . . ?
C22 C23 C18 118.7(3) . . ?
C22 C23 H23 120.6 . . ?
C23 C22 H22 119.2 . . ?
C23 C22 C21 121.6(3) . . ?
C21 C22 H22 119.2 . . ?
C20 C21 C22 121.1(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?

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 N1 C11 C8 -178.68(15) . . . . ?
O1 N1 C11 C12 0.4(2) . . . . ?
O1 C13 C15 C16 -64.8(2) . . . . ?
O1 C13 C12 C11 0.2(2) . . . . ?
O2 C16 C15 C13 72.6(2) . . . . ?
O2 C16 C17 C18 -0.5(3) . . . . ?
O2 C19 C18 C17 -0.3(3) . . . . ?
O2 C19 C18 C23 179.6(2) . . . . ?
O2 C19 C20 C21 -179.3(3) . . . . ?
N1 O1 C13 C15 -117.86(18) . . . . ?
N1 O1 C13 C12 0.0(2) . . . . ?
N1 O1 C13 C14 120.16(18) . . . . ?
N1 C11 C12 C13 -0.4(3) . . . . ?
C8 C11 C12 C13 178.67(17) . . . . ?
C8 C9 C10 C1 179.45(18) . . . . ?
C8 C9 C10 C5 -0.3(3) . . . . ?
C8 C7 C6 C5 -0.3(3) . . . . ?
C11 C8 C9 C10 -179.05(16) . . . . ?
C11 C8 C7 C6 179.36(18) . . . . ?
C9 C8 C11 N1 168.29(17) . . . . ?
C9 C8 C11 C12 -10.7(3) . . . . ?
C9 C8 C7 C6 0.4(3) . . . . ?
C9 C10 C5 C6 0.5(3) . . . . ?
C9 C10 C5 C4 -178.99(19) . . . . ?
C7 C8 C11 N1 -10.6(3) . . . . ?
C7 C8 C11 C12 170.4(2) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C7 C6 C5 C10 -0.2(3) . . . . ?
C7 C6 C5 C4 179.2(2) . . . . ?
C13 O1 N1 C11 -0.3(2) . . . . ?
C16 O2 C19 C18 0.0(2) . . . . ?
C16 O2 C19 C20 179.7(3) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C16 C17 C18 C23 -179.4(3) . . . . ?
C1 C10 C5 C6 -179.31(19) . . . . ?
C1 C10 C5 C4 1.2(3) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C10 C1 C2 C3 -0.8(4) . . . . ?
C10 C5 C4 C3 -1.2(4) . . . . ?
C15 C13 C12 C11 115.4(2) . . . . ?
C15 C16 C17 C18 179.1(2) . . . . ?
C6 C5 C4 C3 179.3(3) . . . . ?
C5 C4 C3 C2 0.2(4) . . . . ?
C17 C16 C15 C13 -107.0(3) . . . . ?
C17 C18 C23 C22 -179.8(3) . . . . ?
C19 O2 C16 C15 -179.40(17) . . . . ?
C19 O2 C16 C17 0.3(2) . . . . ?
C19 C18 C23 C22 0.4(5) . . . . ?
C19 C20 C21 C22 -0.8(5) . . . . ?
C12 C13 C15 C16 -177.69(18) . . . . ?
C14 C13 C15 C16 53.1(3) . . . . ?
C14 C13 C12 C11 -115.5(2) . . . . ?
C18 C19 C20 C21 0.3(4) . . . . ?
C18 C23 C22 C21 -0.9(6) . . . . ?
C2 C1 C10 C9 180.0(2) . . . . ?
C2 C1 C10 C5 -0.2(3) . . . . ?
C20 C19 C18 C17 -180.0(3) . . . . ?
C20 C19 C18 C23 -0.1(4) . . . . ?
C23 C22 C21 C20 1.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
