# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_m1
_database_code_depnum_ccdc_archive 'CCDC 2516694'
loop_
_audit_author_name
_audit_author_address
zhangyang
;School of Pharmacy, Jilin University
China
;
_audit_update_record             
;
2026-04-29 deposited with the CCDC.	2026-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 Cl N O4'
_chemical_formula_weight         395.82

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   13.382(2)
_cell_length_b                   17.484(2)
_cell_length_c                   8.4966(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.374(7)
_cell_angle_gamma                90
_cell_volume                     1925.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.227
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31642
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.143
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4403
_reflns_number_gt                4037
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.989
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.991

_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       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0913P)²+0.4683P] 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-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1896 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4403
_refine_ls_number_parameters     255
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1304
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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
Cl1 Cl 0.82929(9) 0.50064(6) 0.25620(14) 0.0727(3) Uani 1 1 d . . . . .
O1 O 0.3329(2) 0.41139(17) 0.2603(5) 0.0745(8) Uani 1 1 d . . . . .
O2 O 0.27247(18) 0.23622(16) 0.2752(3) 0.0562(6) Uani 1 1 d . . . . .
O3 O 0.4051(4) 0.35639(19) 0.6979(4) 0.0875(11) Uani 1 1 d . . . . .
O4 O 0.4013(3) 0.2443(2) 0.8196(4) 0.0831(10) Uani 1 1 d . . . . .
N1 N 0.4699(2) 0.33116(15) 0.3763(3) 0.0457(6) Uani 1 1 d . . . . .
C1 C 0.7228(3) 0.45142(19) 0.2890(4) 0.0536(7) Uani 1 1 d . . . . .
C2 C 0.6251(3) 0.4754(2) 0.2159(5) 0.0603(8) Uani 1 1 d . . . . .
H2 H 0.615337 0.517973 0.148176 0.072 Uiso 1 1 calc R U . . .
C3 C 0.5403(3) 0.4362(2) 0.2426(4) 0.0571(8) Uani 1 1 d . . . . .
H3 H 0.473909 0.452728 0.192595 0.069 Uiso 1 1 calc R U . . .
C4 C 0.5544(2) 0.37218(17) 0.3442(3) 0.0440(6) Uani 1 1 d . . . . .
C5 C 0.6549(3) 0.34829(19) 0.4137(4) 0.0502(7) Uani 1 1 d . . . . .
H5 H 0.665792 0.304865 0.478902 0.060 Uiso 1 1 calc R U . . .
C6 C 0.7388(3) 0.3876(2) 0.3878(5) 0.0540(7) Uani 1 1 d . . . . .
H6 H 0.805485 0.371338 0.436548 0.065 Uiso 1 1 calc R U . . .
C7 C 0.3682(2) 0.3544(2) 0.3330(4) 0.0521(7) Uani 1 1 d . . . . .
C8 C 0.4888(2) 0.26093(16) 0.4763(4) 0.0422(6) Uani 1 1 d . . . . .
H8 H 0.543287 0.272035 0.574134 0.051 Uiso 1 1 calc R U . . .
C9 C 0.3851(2) 0.24940(18) 0.5288(4) 0.0474(6) Uani 1 1 d . . . . .
C10 C 0.3068(2) 0.2949(2) 0.3947(4) 0.0505(7) Uani 1 1 d . . . . .
C11 C 0.3346(3) 0.1699(2) 0.5131(5) 0.0573(8) Uani 1 1 d . . . . .
H11A H 0.321306 0.153123 0.614742 0.069 Uiso 1 1 calc R U . . .
H11B H 0.376286 0.132011 0.475482 0.069 Uiso 1 1 calc R U . . .
C12 C 0.2326(3) 0.1871(3) 0.3824(5) 0.0650(9) Uani 1 1 d . . . . .
H12 H 0.195965 0.141689 0.330119 0.078 Uiso 1 1 calc R U . . .
C13 C 0.1674(3) 0.2418(3) 0.4503(6) 0.0751(12) Uani 1 1 d . . . . .
H13 H 0.107779 0.230053 0.482876 0.090 Uiso 1 1 calc R U . . .
C14 C 0.2109(3) 0.3096(3) 0.4547(5) 0.0652(10) Uani 1 1 d . . . . .
H14 H 0.188002 0.355819 0.487135 0.078 Uiso 1 1 calc R U . . .
C15 C 0.5237(2) 0.19392(17) 0.3904(4) 0.0440(6) Uani 1 1 d . . . . .
C16 C 0.4909(3) 0.1816(2) 0.2248(4) 0.0526(7) Uani 1 1 d . . . . .
H16 H 0.446807 0.216645 0.159951 0.063 Uiso 1 1 calc R U . . .
C17 C 0.5229(3) 0.1178(3) 0.1546(5) 0.0658(10) Uani 1 1 d . . . . .
H17 H 0.499215 0.109586 0.043415 0.079 Uiso 1 1 calc R U . . .
C18 C 0.5905(4) 0.0659(3) 0.2501(6) 0.0724(12) Uani 1 1 d . . . . .
H18 H 0.611675 0.022669 0.203324 0.087 Uiso 1 1 calc R U . . .
C19 C 0.6256(4) 0.0788(2) 0.4137(6) 0.0723(11) Uani 1 1 d . . . . .
H19 H 0.671670 0.044566 0.477290 0.087 Uiso 1 1 calc R U . . .
C20 C 0.5933(3) 0.1422(2) 0.4854(5) 0.0574(8) Uani 1 1 d . . . . .
H20 H 0.617690 0.150461 0.596438 0.069 Uiso 1 1 calc R U . . .
C21 C 0.3977(3) 0.2821(2) 0.6980(4) 0.0562(8) Uani 1 1 d . . . . .
C22 C 0.4080(7) 0.3932(4) 0.8528(7) 0.105(2) Uani 1 1 d . . . . .
H22A H 0.372393 0.441289 0.833706 0.157 Uiso 1 1 calc R U . . .
H22B H 0.478445 0.401781 0.910591 0.157 Uiso 1 1 calc R U . . .
H22C H 0.375153 0.360859 0.916227 0.157 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
Cl1 C1 1.745(4) . ?
O1 C7 1.206(5) . ?
O2 C10 1.435(4) . ?
O2 C12 1.446(5) . ?
O3 C21 1.303(5) . ?
O3 C22 1.457(6) . ?
O4 C21 1.217(5) . ?
N1 C7 1.379(4) . ?
N1 C4 1.422(4) . ?
N1 C8 1.479(4) . ?
C1 C2 1.366(6) . ?
C1 C6 1.381(5) . ?
C2 C3 1.392(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(4) . ?
C5 C6 1.380(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C10 1.499(5) . ?
C8 C15 1.514(4) . ?
C8 C9 1.572(4) . ?
C8 H8 0.9800 . ?
C9 C21 1.517(4) . ?
C9 C11 1.536(5) . ?
C9 C10 1.560(5) . ?
C10 C14 1.516(5) . ?
C11 C12 1.560(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.503(7) . ?
C12 H12 0.9800 . ?
C13 C14 1.316(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.383(5) . ?
C15 C20 1.400(5) . ?
C16 C17 1.382(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C10 O2 C12 94.7(3) . . ?
C21 O3 C22 115.1(4) . . ?
C7 N1 C4 125.4(3) . . ?
C7 N1 C8 114.5(3) . . ?
C4 N1 C8 119.9(2) . . ?
C2 C1 C6 120.7(3) . . ?
C2 C1 Cl1 120.2(3) . . ?
C6 C1 Cl1 119.1(3) . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 N1 119.9(3) . . ?
C3 C4 N1 122.0(3) . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
O1 C7 N1 128.0(3) . . ?
O1 C7 C10 125.0(3) . . ?
N1 C7 C10 107.0(3) . . ?
N1 C8 C15 113.3(2) . . ?
N1 C8 C9 103.4(2) . . ?
C15 C8 C9 115.9(2) . . ?
N1 C8 H8 107.9 . . ?
C15 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
C21 C9 C11 111.5(3) . . ?
C21 C9 C10 113.4(3) . . ?
C11 C9 C10 101.3(3) . . ?
C21 C9 C8 108.8(3) . . ?
C11 C9 C8 119.4(3) . . ?
C10 C9 C8 102.0(2) . . ?
O2 C10 C7 110.8(3) . . ?
O2 C10 C14 102.1(3) . . ?
C7 C10 C14 125.7(3) . . ?
O2 C10 C9 101.0(3) . . ?
C7 C10 C9 106.3(3) . . ?
C14 C10 C9 108.2(3) . . ?
C9 C11 C12 100.1(3) . . ?
C9 C11 H11A 111.7 . . ?
C12 C11 H11A 111.7 . . ?
C9 C11 H11B 111.7 . . ?
C12 C11 H11B 111.7 . . ?
H11A C11 H11B 109.5 . . ?
O2 C12 C13 101.8(4) . . ?
O2 C12 C11 99.7(3) . . ?
C13 C12 C11 109.8(3) . . ?
O2 C12 H12 114.6 . . ?
C13 C12 H12 114.6 . . ?
C11 C12 H12 114.6 . . ?
C14 C13 C12 106.8(3) . . ?
C14 C13 H13 126.6 . . ?
C12 C13 H13 126.6 . . ?
C13 C14 C10 104.0(4) . . ?
C13 C14 H14 128.0 . . ?
C10 C14 H14 128.0 . . ?
C16 C15 C20 118.9(3) . . ?
C16 C15 C8 123.5(3) . . ?
C20 C15 C8 117.5(3) . . ?
C15 C16 C17 120.7(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 120.1(4) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.8(4) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C15 119.9(4) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
O4 C21 O3 123.7(4) . . ?
O4 C21 C9 124.9(4) . . ?
O3 C21 C9 111.4(3) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.656
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.043

