# Supplementary Information (SI) for Chemical Science.
# 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_20250108
_database_code_depnum_ccdc_archive 'CCDC 2473530'
loop_
_audit_author_name
_audit_author_address
OLC-B
;Zhengzhou University
China
;
_audit_update_record             
;
2025-07-17 deposited with the CCDC.	2026-04-28 downloaded from the CCDC.
;
_audit_creation_date             2025-01-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H12 Cl N O2'
_chemical_formula_sum            'C10 H12 Cl N O2'
_chemical_formula_weight         213.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H32O3N3Cl1
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'
Cl Cl 0.3639 0.7018 '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                   11.3905(5)
_cell_length_b                   10.3427(7)
_cell_length_c                   9.0688(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.417(4)
_cell_angle_gamma                90
_cell_volume                     1068.07(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1364
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9150
_cell_measurement_theta_min      4.2710
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.617
_exptl_absorpt_coefficient_mu    2.969
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3868
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.027
_diffrn_reflns_theta_max         67.027
_diffrn_reflns_theta_min         3.882
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -11.00   1.00    5.00    --  -33.50 -37.00  90.00   93
  2  ω     28.00  95.00   1.00    5.00    --   36.53-133.00 -63.00   67
  3  ω     61.00 111.00   1.00    5.00    --   36.53 178.00  90.00   50
  4  ω     78.00 103.00   1.00    5.00    --   36.53 178.00-120.00   25
  5  ω    -32.00  18.00   1.00    5.00    --   36.53   0.00-180.00   50
  6  ω      8.00  47.00   1.00    5.00    --   36.53 -37.00 -30.00   39
  7  ω     53.00  99.00   1.00    5.00    --   36.53   0.00-180.00   46
  8  ω    102.00 169.00   1.00   15.00    --  108.00  77.00-150.00   67
  9  ω     75.00 106.00   1.00   15.00    --  108.00 -94.00-120.00   31
 10  ω    104.00 165.00   1.00   15.00    --  108.00  77.00-120.00   61
 11  ω     38.00  68.00   1.00   15.00    --  108.00 -94.00-120.00   30
 12  ω     42.00 105.00   1.00   15.00    --  108.00-111.00-150.00   63
 13  ω     82.00 124.00   1.00   15.00    --  108.00 -45.00  30.00   42
 14  ω     39.00 127.00   1.00   15.00    --  108.00 -45.00-150.00   88
 15  ω    109.00 178.00   1.00   15.00    --  108.00  45.00 150.00   69
 16  ω     91.00 132.00   1.00   15.00    --  108.00 -77.00 -60.00   41
 17  ω     58.00  85.00   1.00   15.00    --  108.00 -77.00 -60.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1169450000
_diffrn_orient_matrix_UB_12      -0.0748209000
_diffrn_orient_matrix_UB_13      0.0073198000
_diffrn_orient_matrix_UB_21      -0.0680851000
_diffrn_orient_matrix_UB_22      -0.1285557000
_diffrn_orient_matrix_UB_23      0.0068952000
_diffrn_orient_matrix_UB_31      -0.0010794000
_diffrn_orient_matrix_UB_32      -0.0084058000
_diffrn_orient_matrix_UB_33      -0.1695511000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1415
_reflns_number_total             1909
_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       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1909
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0722
_refine_ls_restrained_S_all      1.072
_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)+(0.1423P)²+0.0900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2065
_refine_ls_wR_factor_ref         0.2315
_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. Restrained distances
 H1-N1
 0.87 with sigma of 0.02
 O2-H2
 0.9 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Cl1 Cl 0.81482(9) 0.25298(12) 0.40958(13) 0.0740(5) Uani 1 1 d . . . . .
O1 O 0.4918(3) 0.2880(4) 0.1070(3) 0.0692(9) Uani 1 1 d . . . . .
O2 O 0.5924(2) 0.4071(2) 0.4580(2) 0.0449(6) Uani 1 1 d D . . . .
H2 H 0.572(5) 0.340(4) 0.508(5) 0.085(17) Uiso 1 1 d D . . . .
N1 N 0.3986(2) 0.3907(3) 0.2919(3) 0.0450(7) Uani 1 1 d D . . . .
H1 H 0.415(3) 0.422(3) 0.381(2) 0.041(9) Uiso 1 1 d D . . . .
C1 C 0.4941(3) 0.3437(3) 0.2278(4) 0.0448(8) Uani 1 1 d . . . . .
C2 C 0.6116(3) 0.3679(3) 0.3116(3) 0.0417(8) Uani 1 1 d . . . . .
C3 C 0.6793(3) 0.2408(4) 0.3074(4) 0.0493(9) Uani 1 1 d . . . . .
H3A H 0.694939 0.218585 0.205887 0.059 Uiso 1 1 calc R U . . .
H3B H 0.632013 0.172400 0.348670 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6747(4) 0.4788(5) 0.2345(5) 0.0661(11) Uani 1 1 d . . . . .
H4A H 0.631349 0.557470 0.246894 0.099 Uiso 1 1 calc R U . . .
H4B H 0.679990 0.459704 0.131275 0.099 Uiso 1 1 calc R U . . .
H4C H 0.752189 0.488611 0.276964 0.099 Uiso 1 1 calc R U . . .
C5 C 0.2794(3) 0.3884(3) 0.2402(4) 0.0437(8) Uani 1 1 d . . . . .
C6 C 0.1979(3) 0.4482(4) 0.3293(4) 0.0537(9) Uani 1 1 d . . . . .
H6 H 0.222430 0.486552 0.417526 0.064 Uiso 1 1 calc R U . . .
C7 C 0.0811(3) 0.4508(5) 0.2872(4) 0.0636(11) Uani 1 1 d . . . . .
H7 H 0.026953 0.490779 0.347261 0.076 Uiso 1 1 calc R U . . .
C8 C 0.0444(4) 0.3951(5) 0.1576(5) 0.0717(12) Uani 1 1 d . . . . .
H8 H -0.034723 0.396876 0.129771 0.086 Uiso 1 1 calc R U . . .
C9 C 0.1239(4) 0.3365(5) 0.0687(5) 0.0754(13) Uani 1 1 d . . . . .
H9 H 0.098285 0.298778 -0.019421 0.091 Uiso 1 1 calc R U . . .
C10 C 0.2425(4) 0.3328(4) 0.1085(5) 0.0623(11) Uani 1 1 d . . . . .
H10 H 0.296275 0.293349 0.047334 0.075 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 C3 1.785(4) . ?
O1 C1 1.238(4) . ?
O2 H2 0.87(2) . ?
O2 C2 1.411(4) . ?
N1 H1 0.883(18) . ?
N1 C1 1.337(4) . ?
N1 C5 1.425(4) . ?
C1 C2 1.543(4) . ?
C2 C3 1.525(5) . ?
C2 C4 1.532(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.391(5) . ?
C5 C10 1.382(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.365(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.369(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(6) . ?
C10 H10 0.9300 . ?

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 O2 H2 108(4) . . ?
C1 N1 H1 112(2) . . ?
C1 N1 C5 129.0(3) . . ?
C5 N1 H1 119(2) . . ?
O1 C1 N1 123.6(3) . . ?
O1 C1 C2 120.7(3) . . ?
N1 C1 C2 115.6(3) . . ?
O2 C2 C1 110.9(2) . . ?
O2 C2 C3 111.2(3) . . ?
O2 C2 C4 107.4(3) . . ?
C3 C2 C1 106.3(3) . . ?
C3 C2 C4 113.0(3) . . ?
C4 C2 C1 107.9(3) . . ?
Cl1 C3 H3A 109.4 . . ?
Cl1 C3 H3B 109.4 . . ?
C2 C3 Cl1 111.0(2) . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 116.5(3) . . ?
C10 C5 N1 123.9(3) . . ?
C10 C5 C6 119.6(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.3(4) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0(4) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
C5 C10 C9 119.0(4) . . ?
C5 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?

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
O2 H2 O1 0.87(2) 1.85(2) 2.699(4) 166(5) 4_566 yes
N1 H1 O2 0.883(18) 2.30(3) 3.085(4) 148(3) 3_666 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 C1 C2 O2 -167.6(3) . . . . ?
O1 C1 C2 C3 -46.5(5) . . . . ?
O1 C1 C2 C4 75.0(4) . . . . ?
O2 C2 C3 Cl1 -56.1(3) . . . . ?
N1 C1 C2 O2 14.7(4) . . . . ?
N1 C1 C2 C3 135.8(3) . . . . ?
N1 C1 C2 C4 -102.7(4) . . . . ?
N1 C5 C6 C7 179.7(4) . . . . ?
N1 C5 C10 C9 -179.8(4) . . . . ?
C1 N1 C5 C6 -178.4(4) . . . . ?
C1 N1 C5 C10 0.6(6) . . . . ?
C1 C2 C3 Cl1 -176.9(2) . . . . ?
C4 C2 C3 Cl1 64.9(4) . . . . ?
C5 N1 C1 O1 -0.1(6) . . . . ?
C5 N1 C1 C2 177.5(3) . . . . ?
C5 C6 C7 C8 -0.1(7) . . . . ?
C6 C5 C10 C9 -0.8(7) . . . . ?
C6 C7 C8 C9 -0.2(8) . . . . ?
C7 C8 C9 C10 0.0(8) . . . . ?
C8 C9 C10 C5 0.4(8) . . . . ?
C10 C5 C6 C7 0.6(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.239
_oxdiff_exptl_absorpt_empirical_full_min 0.825
