# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1
_database_code_depnum_ccdc_archive 'CCDC 2488345'
loop_
_audit_author_name
_audit_author_address
'jian lei'
;quanzhou normal university
China
;
_audit_update_record             
;
2025-09-15 deposited with the CCDC.	2026-01-21 downloaded from the CCDC.
;
_audit_creation_date             2023-06-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 Cl N2 O4'
_chemical_formula_sum            'C14 H15 Cl N2 O4'
_chemical_formula_weight         310.73
_chemical_absolute_configuration AD
_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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.4462(14)
_cell_length_b                   5.7838(8)
_cell_length_c                   12.6355(16)
_cell_angle_alpha                90
_cell_angle_beta                 105.683(5)
_cell_angle_gamma                90
_cell_volume                     735.00(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6125
_cell_measurement_temperature    298.30
_cell_measurement_theta_max      56.892
_cell_measurement_theta_min      4.253
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1593 before and 0.0706 after correction.
The Ratio of minimum to maximum transmission is 0.7097.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7209
_diffrn_reflns_point_group_measured_fraction_full 0.888
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.401
_diffrn_reflns_theta_min         1.674
_diffrn_ambient_temperature      298.30
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.589
_reflns_Friedel_fraction_full    0.759
_reflns_Friedel_fraction_max     0.718
_reflns_number_gt                2453
_reflns_number_total             2613
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 871 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.89(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2613
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      0.894
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1084
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C10(H10), C14(H14), C13(H13), C11(H11)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_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
Cl01 Cl 0.78024(8) 1.17798(16) 0.43058(5) 0.0468(3) Uani 1 1 d . . . . .
O4 O 0.68896(15) 0.4174(4) 0.80874(14) 0.0266(4) Uani 1 1 d . . . . .
O3 O 0.66971(18) 0.1292(4) 0.92619(15) 0.0336(5) Uani 1 1 d . . . . .
O1 O 0.22181(16) 0.1987(4) 0.89416(14) 0.0306(4) Uani 1 1 d . . . . .
O2 O 0.34159(17) 0.1218(4) 0.77180(14) 0.0321(5) Uani 1 1 d . . . . .
N1 N 0.42078(19) 0.3524(4) 0.92241(17) 0.0273(5) Uani 1 1 d . . . . .
H1 H 0.418391 0.384183 0.988330 0.033 Uiso 1 1 calc R U . . .
N2 N 0.51931(19) 0.4357(4) 0.87848(17) 0.0264(5) Uani 1 1 d . . . . .
C5 C 0.3259(2) 0.2138(5) 0.8528(2) 0.0252(5) Uani 1 1 d . . . . .
C9 C 0.6529(2) 0.7447(5) 0.6823(2) 0.0266(6) Uani 1 1 d . . . . .
C6 C 0.6290(2) 0.3077(5) 0.8779(2) 0.0241(5) Uani 1 1 d . . . . .
C7 C 0.5055(2) 0.6174(5) 0.8036(2) 0.0270(5) Uani 1 1 d . . . . .
H7 H 0.436371 0.724119 0.785659 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6105(2) 0.6085(5) 0.76253(19) 0.0264(5) Uani 1 1 d . . . . .
C10 C 0.5900(2) 0.9551(5) 0.6460(2) 0.0293(6) Uani 1 1 d . . . . .
H10 H 0.522421 1.007660 0.674989 0.035 Uiso 1 1 calc R U . . .
C14 C 0.7542(2) 0.6673(6) 0.6369(2) 0.0310(6) Uani 1 1 d . . . . .
H14 H 0.796801 0.527772 0.660015 0.037 Uiso 1 1 calc R U . . .
C13 C 0.7909(3) 0.7979(6) 0.5577(2) 0.0357(6) Uani 1 1 d . . . . .
H13 H 0.857271 0.745727 0.527137 0.043 Uiso 1 1 calc R U . . .
C3 C 0.1203(3) -0.1767(5) 0.8299(3) 0.0366(7) Uani 1 1 d . . . . .
H3A H 0.187549 -0.210188 0.793192 0.055 Uiso 1 1 calc R U . . .
H3B H 0.038890 -0.251888 0.792030 0.055 Uiso 1 1 calc R U . . .
H3C H 0.148620 -0.232168 0.904208 0.055 Uiso 1 1 calc R U . . .
C11 C 0.6272(3) 1.0861(6) 0.5673(2) 0.0340(6) Uani 1 1 d . . . . .
H11 H 0.585248 1.225795 0.543402 0.041 Uiso 1 1 calc R U . . .
C2 C 0.0982(2) 0.0820(5) 0.8303(2) 0.0312(6) Uani 1 1 d . . . . .
C4 C 0.0526(3) 0.1829(7) 0.7156(3) 0.0411(7) Uani 1 1 d . . . . .
H4A H 0.054599 0.348668 0.720031 0.062 Uiso 1 1 calc R U . . .
H4B H -0.036408 0.132417 0.681053 0.062 Uiso 1 1 calc R U . . .
H4C H 0.110803 0.131732 0.673167 0.062 Uiso 1 1 calc R U . . .
C12 C 0.7283(3) 1.0052(6) 0.5248(2) 0.0341(6) Uani 1 1 d . . . . .
C1 C 0.0015(3) 0.1436(8) 0.8966(3) 0.0496(9) Uani 1 1 d . . . . .
H1A H 0.037593 0.095588 0.971498 0.074 Uiso 1 1 calc R U . . .
H1B H -0.081642 0.066470 0.866059 0.074 Uiso 1 1 calc R U . . .
H1C H -0.012503 0.307802 0.894219 0.074 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
Cl01 C12 1.749(3) . ?
O4 C6 1.362(3) . ?
O4 C8 1.405(3) . ?
O3 C6 1.216(3) . ?
O1 C5 1.330(3) . ?
O1 C2 1.487(3) . ?
O2 C5 1.204(3) . ?
N1 H1 0.8600 . ?
N1 N2 1.382(3) . ?
N1 C5 1.388(3) . ?
N2 C6 1.365(3) . ?
N2 C7 1.395(4) . ?
C9 C8 1.445(4) . ?
C9 C10 1.400(4) . ?
C9 C14 1.406(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.335(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.388(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.375(5) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3 C2 1.515(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(4) . ?
C2 C4 1.515(4) . ?
C2 C1 1.518(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
C6 O4 C8 108.36(19) . . ?
C5 O1 C2 119.9(2) . . ?
N2 N1 H1 122.3 . . ?
N2 N1 C5 115.4(2) . . ?
C5 N1 H1 122.3 . . ?
N1 N2 C7 125.7(2) . . ?
C6 N2 N1 122.0(2) . . ?
C6 N2 C7 109.8(2) . . ?
O1 C5 N1 108.0(2) . . ?
O2 C5 O1 128.2(2) . . ?
O2 C5 N1 123.8(2) . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 C14 118.8(3) . . ?
C14 C9 C8 121.3(3) . . ?
O4 C6 N2 106.4(2) . . ?
O3 C6 O4 123.9(2) . . ?
O3 C6 N2 129.7(2) . . ?
N2 C7 H7 126.6 . . ?
C8 C7 N2 106.8(2) . . ?
C8 C7 H7 126.6 . . ?
O4 C8 C9 117.7(2) . . ?
C7 C8 O4 108.5(2) . . ?
C7 C8 C9 133.7(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C14 C13 H13 120.3 . . ?
C12 C13 C14 119.4(3) . . ?
C12 C13 H13 120.3 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 118.9(3) . . ?
C12 C11 H11 120.5 . . ?
O1 C2 C3 109.8(2) . . ?
O1 C2 C4 110.2(2) . . ?
O1 C2 C1 101.8(2) . . ?
C3 C2 C4 112.7(3) . . ?
C3 C2 C1 111.0(3) . . ?
C4 C2 C1 110.7(3) . . ?
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 . . ?
C13 C12 Cl01 119.6(2) . . ?
C13 C12 C11 121.7(3) . . ?
C11 C12 Cl01 118.6(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
N1 N2 C6 O4 166.9(2) . . . . ?
N1 N2 C6 O3 -12.2(4) . . . . ?
N1 N2 C7 C8 -165.8(2) . . . . ?
N2 N1 C5 O1 -163.8(2) . . . . ?
N2 N1 C5 O2 18.1(4) . . . . ?
N2 C7 C8 O4 1.7(3) . . . . ?
N2 C7 C8 C9 179.4(3) . . . . ?
C5 O1 C2 C3 72.3(3) . . . . ?
C5 O1 C2 C4 -52.5(3) . . . . ?
C5 O1 C2 C1 -170.0(3) . . . . ?
C5 N1 N2 C6 -83.5(3) . . . . ?
C5 N1 N2 C7 76.6(3) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C9 C14 C13 C12 0.7(4) . . . . ?
C6 O4 C8 C9 -177.3(2) . . . . ?
C6 O4 C8 C7 0.7(3) . . . . ?
C6 N2 C7 C8 -3.7(3) . . . . ?
C7 N2 C6 O4 4.1(3) . . . . ?
C7 N2 C6 O3 -175.0(3) . . . . ?
C8 O4 C6 O3 176.2(2) . . . . ?
C8 O4 C6 N2 -2.9(2) . . . . ?
C8 C9 C10 C11 -178.6(2) . . . . ?
C8 C9 C14 C13 178.2(2) . . . . ?
C10 C9 C8 O4 -170.6(2) . . . . ?
C10 C9 C8 C7 12.0(4) . . . . ?
C10 C9 C14 C13 0.1(4) . . . . ?
C10 C11 C12 Cl01 -176.9(2) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C14 C9 C8 O4 11.3(3) . . . . ?
C14 C9 C8 C7 -166.1(3) . . . . ?
C14 C9 C10 C11 -0.5(4) . . . . ?
C14 C13 C12 Cl01 176.5(2) . . . . ?
C14 C13 C12 C11 -1.1(4) . . . . ?
C2 O1 C5 O2 -8.8(4) . . . . ?
C2 O1 C5 N1 173.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
