# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_d8v23041_0m
_database_code_depnum_ccdc_archive 'CCDC 2240048'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2023-02-06 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.6372(4)
_cell_length_b                   18.5055(9)
_cell_length_c                   12.0312(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.348(2)
_cell_angle_gamma                90
_cell_volume                     1623.02(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3470
_cell_measurement_theta_min      5.654
_cell_measurement_theta_max      53.868

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4526
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7981
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.827
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3168
_reflns_number_gt                2441
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0624P)²+0.3612P] 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     SHELXL
_refine_ls_extinction_coef       0.058(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3168
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1278
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_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
O1 O 0.5281(2) 0.86406(9) 0.65641(12) 0.0702(5) Uani 1 1 d . . . . .
O2 O 0.1379(2) 0.90614(8) 0.41737(17) 0.0759(5) Uani 1 1 d . . . . .
N1 N 0.5619(2) 0.87223(7) 0.47699(13) 0.0432(4) Uani 1 1 d . . . . .
C1 C 0.4960(2) 0.86165(9) 0.35425(15) 0.0379(4) Uani 1 1 d . . . . .
C2 C 0.4986(3) 0.92043(9) 0.28233(18) 0.0487(5) Uani 1 1 d . . . . .
H2 H 0.5388 0.9651 0.3155 0.058 Uiso 1 1 calc R U . . .
C3 C 0.4429(3) 0.91348(10) 0.16381(19) 0.0546(5) Uani 1 1 d . . . . .
H3 H 0.4489 0.9531 0.1174 0.065 Uiso 1 1 calc R U . . .
C4 C 0.3779(3) 0.84811(11) 0.11238(17) 0.0510(5) Uani 1 1 d . . . . .
H4 H 0.3369 0.8437 0.0317 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3750(2) 0.78949(10) 0.18292(15) 0.0423(4) Uani 1 1 d . . . . .
H5 H 0.3316 0.7454 0.1485 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4350(2) 0.79434(8) 0.30421(14) 0.0342(4) Uani 1 1 d . . . . .
C7 C 0.4250(2) 0.72883(8) 0.37313(13) 0.0337(4) Uani 1 1 d . . . . .
C8 C 0.4865(2) 0.65836(8) 0.33944(13) 0.0340(4) Uani 1 1 d . . . . .
C9 C 0.6201(2) 0.65295(9) 0.28211(15) 0.0397(4) Uani 1 1 d . . . . .
H9 H 0.6697 0.6948 0.2611 0.048 Uiso 1 1 calc R U . . .
C10 C 0.6801(3) 0.58628(10) 0.25604(17) 0.0489(5) Uani 1 1 d . . . . .
H10 H 0.7709 0.5835 0.2191 0.059 Uiso 1 1 calc R U . . .
C11 C 0.6048(3) 0.52414(10) 0.28495(18) 0.0532(5) Uani 1 1 d . . . . .
H11 H 0.6424 0.4793 0.2657 0.064 Uiso 1 1 calc R U . . .
C12 C 0.4731(3) 0.52835(9) 0.34258(16) 0.0476(5) Uani 1 1 d . . . . .
H12 H 0.4232 0.4861 0.3620 0.057 Uiso 1 1 calc R U . . .
C13 C 0.4144(2) 0.59445(9) 0.37181(15) 0.0378(4) Uani 1 1 d . . . . .
C14 C 0.2756(3) 0.60130(9) 0.43718(16) 0.0439(4) Uani 1 1 d . . . . .
H14A H 0.2698 0.5565 0.4778 0.053 Uiso 1 1 calc R U . . .
H14B H 0.1554 0.6105 0.3830 0.053 Uiso 1 1 calc R U . . .
C15 C 0.3287(3) 0.66274(9) 0.52402(15) 0.0438(5) Uani 1 1 d . . . . .
H15A H 0.2332 0.6699 0.5610 0.053 Uiso 1 1 calc R U . . .
H15B H 0.4414 0.6507 0.5840 0.053 Uiso 1 1 calc R U . . .
C16 C 0.3554(2) 0.73125(8) 0.46329(14) 0.0361(4) Uani 1 1 d . . . . .
C17 C 0.3043(2) 0.80234(9) 0.50655(14) 0.0391(4) Uani 1 1 d . . . . .
H17 H 0.2644 0.7901 0.5744 0.047 Uiso 1 1 calc R U . . .
C18 C 0.4723(3) 0.84943(10) 0.55348(16) 0.0445(5) Uani 1 1 d . . . . .
C19 C 0.1413(2) 0.84148(10) 0.42306(16) 0.0449(5) Uani 1 1 d . . . . .
C20 C -0.0166(3) 0.79622(12) 0.3571(2) 0.0648(6) Uani 1 1 d . . . . .
H20A H -0.0568 0.7667 0.4104 0.097 Uiso 1 1 calc R U . . .
H20B H 0.0205 0.7658 0.3035 0.097 Uiso 1 1 calc R U . . .
H20C H -0.1154 0.8269 0.3148 0.097 Uiso 1 1 calc R U . . .
C21 C 0.7193(3) 0.92108(11) 0.5248(2) 0.0621(6) Uani 1 1 d . . . . .
H21A H 0.7986 0.9196 0.4761 0.093 Uiso 1 1 calc R U . . .
H21B H 0.7861 0.9059 0.6021 0.093 Uiso 1 1 calc R U . . .
H21C H 0.6756 0.9695 0.5272 0.093 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 C18 1.214(2) . ?
O2 C19 1.198(2) . ?
N1 C18 1.367(2) . ?
N1 C1 1.424(2) . ?
N1 C21 1.477(2) . ?
C1 C2 1.394(2) . ?
C1 C6 1.401(2) . ?
C2 C3 1.367(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.483(2) . ?
C7 C16 1.344(2) . ?
C7 C8 1.483(2) . ?
C8 C9 1.395(2) . ?
C8 C13 1.408(2) . ?
C9 C10 1.384(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.501(2) . ?
C14 C15 1.515(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.507(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.508(2) . ?
C17 C18 1.514(2) . ?
C17 C19 1.529(3) . ?
C17 H17 0.9800 . ?
C19 C20 1.489(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C18 N1 C1 124.19(14) . . ?
C18 N1 C21 116.10(15) . . ?
C1 N1 C21 118.88(15) . . ?
C2 C1 C6 119.44(16) . . ?
C2 C1 N1 118.05(15) . . ?
C6 C1 N1 122.49(15) . . ?
C3 C2 C1 121.10(17) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.53(17) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 118.80(18) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.09(17) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 118.01(15) . . ?
C5 C6 C7 118.44(14) . . ?
C1 C6 C7 123.51(15) . . ?
C16 C7 C8 118.94(14) . . ?
C16 C7 C6 121.52(14) . . ?
C8 C7 C6 119.50(13) . . ?
C9 C8 C13 118.74(14) . . ?
C9 C8 C7 122.44(14) . . ?
C13 C8 C7 118.74(14) . . ?
C10 C9 C8 121.08(16) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 119.74(17) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.05(16) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 121.07(16) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C8 119.27(16) . . ?
C12 C13 C14 122.72(15) . . ?
C8 C13 C14 118.01(14) . . ?
C13 C14 C15 109.82(14) . . ?
C13 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 C14 110.12(14) . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
C7 C16 C15 120.44(14) . . ?
C7 C16 C17 120.85(14) . . ?
C15 C16 C17 118.70(13) . . ?
C16 C17 C18 110.69(14) . . ?
C16 C17 C19 115.48(14) . . ?
C18 C17 C19 113.93(14) . . ?
C16 C17 H17 105.2 . . ?
C18 C17 H17 105.2 . . ?
C19 C17 H17 105.2 . . ?
O1 C18 N1 121.58(17) . . ?
O1 C18 C17 120.64(17) . . ?
N1 C18 C17 117.73(14) . . ?
O2 C19 C20 122.07(18) . . ?
O2 C19 C17 120.69(17) . . ?
C20 C19 C17 117.08(16) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C18 N1 C1 C2 132.93(18) . . . . ?
C21 N1 C1 C2 -36.2(2) . . . . ?
C18 N1 C1 C6 -49.2(2) . . . . ?
C21 N1 C1 C6 141.69(17) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
N1 C1 C2 C3 177.83(17) . . . . ?
C1 C2 C3 C4 1.7(3) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 1.4(3) . . . . ?
C4 C5 C6 C7 179.33(16) . . . . ?
C2 C1 C6 C5 -1.4(2) . . . . ?
N1 C1 C6 C5 -179.25(15) . . . . ?
C2 C1 C6 C7 -179.25(16) . . . . ?
N1 C1 C6 C7 2.9(2) . . . . ?
C5 C6 C7 C16 -133.03(18) . . . . ?
C1 C6 C7 C16 44.8(2) . . . . ?
C5 C6 C7 C8 44.6(2) . . . . ?
C1 C6 C7 C8 -137.54(16) . . . . ?
C16 C7 C8 C9 -154.34(16) . . . . ?
C6 C7 C8 C9 27.9(2) . . . . ?
C16 C7 C8 C13 22.3(2) . . . . ?
C6 C7 C8 C13 -155.41(15) . . . . ?
C13 C8 C9 C10 0.7(3) . . . . ?
C7 C8 C9 C10 177.34(16) . . . . ?
C8 C9 C10 C11 1.2(3) . . . . ?
C9 C10 C11 C12 -1.7(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C8 1.7(3) . . . . ?
C11 C12 C13 C14 -178.28(18) . . . . ?
C9 C8 C13 C12 -2.1(3) . . . . ?
C7 C8 C13 C12 -178.92(15) . . . . ?
C9 C8 C13 C14 177.87(16) . . . . ?
C7 C8 C13 C14 1.1(2) . . . . ?
C12 C13 C14 C15 140.97(18) . . . . ?
C8 C13 C14 C15 -39.0(2) . . . . ?
C13 C14 C15 C16 54.09(19) . . . . ?
C8 C7 C16 C15 -4.0(2) . . . . ?
C6 C7 C16 C15 173.65(16) . . . . ?
C8 C7 C16 C17 175.32(14) . . . . ?
C6 C7 C16 C17 -7.0(2) . . . . ?
C14 C15 C16 C7 -34.5(2) . . . . ?
C14 C15 C16 C17 146.11(15) . . . . ?
C7 C16 C17 C18 -63.7(2) . . . . ?
C15 C16 C17 C18 115.69(17) . . . . ?
C7 C16 C17 C19 67.6(2) . . . . ?
C15 C16 C17 C19 -112.99(17) . . . . ?
C1 N1 C18 O1 -174.94(17) . . . . ?
C21 N1 C18 O1 -5.6(3) . . . . ?
C1 N1 C18 C17 7.6(3) . . . . ?
C21 N1 C18 C17 176.97(15) . . . . ?
C16 C17 C18 O1 -113.28(19) . . . . ?
C19 C17 C18 O1 114.6(2) . . . . ?
C16 C17 C18 N1 64.2(2) . . . . ?
C19 C17 C18 N1 -67.9(2) . . . . ?
C16 C17 C19 O2 -144.91(18) . . . . ?
C18 C17 C19 O2 -15.2(2) . . . . ?
C16 C17 C19 C20 39.6(2) . . . . ?
C18 C17 C19 C20 169.41(16) . . . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4

