# 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_230802wkj159_0m
_database_code_depnum_ccdc_archive 'CCDC 2535858'
loop_
_audit_author_name
_audit_author_address
'Dong Wang'
;Xinjiang University
China
;
_audit_update_record             
;
2026-03-07 deposited with the CCDC.	2026-06-03 downloaded from the CCDC.
;
_audit_creation_date             2023-08-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 Cl N2'
_chemical_formula_sum            'C14 H15 Cl N2'
_chemical_formula_weight         246.73
_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'

_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                   9.6537(11)
_cell_length_b                   15.3596(18)
_cell_length_c                   8.5643(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.813(2)
_cell_angle_gamma                90
_cell_volume                     1260.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2675
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.476
_cell_measurement_theta_min      2.652
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0567 before and 0.0345 after correction.
The Ratio of minimum to maximum transmission is 0.9427.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7495
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.603
_diffrn_reflns_theta_min         2.652
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1983
_reflns_number_total             2789
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.236
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.050
_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)+(0.0601P)²+0.3598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1318
_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:
 C2(H2A,H2B), C5(H5A,H5B), C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C7(H7), C9(H9)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_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
Cl1 Cl 0.11518(6) 0.35481(5) 0.76430(8) 0.0726(2) Uani 1 1 d . . . . .
N1 N 0.59989(16) 0.47949(10) 0.78108(17) 0.0436(4) Uani 1 1 d . . . . .
N2 N 0.69230(17) 0.36019(10) 0.36187(18) 0.0456(4) Uani 1 1 d . . . . .
C1 C 0.50313(18) 0.42786(11) 0.6972(2) 0.0383(4) Uani 1 1 d . . . . .
C4 C 0.52385(18) 0.38490(11) 0.5549(2) 0.0383(4) Uani 1 1 d . . . . .
C6 C 0.65720(18) 0.39667(11) 0.4967(2) 0.0389(4) Uani 1 1 d . . . . .
C8 C 0.72150(19) 0.48641(12) 0.7271(2) 0.0440(4) Uani 1 1 d . . . . .
C10 C 0.37588(19) 0.41729(12) 0.7616(2) 0.0450(4) Uani 1 1 d . . . . .
H10 H 0.361984 0.445790 0.854249 0.054 Uiso 1 1 calc R U . . .
C12 C 0.75409(19) 0.44608(13) 0.5906(2) 0.0445(4) Uani 1 1 d . . . . .
H12 H 0.843384 0.452473 0.561684 0.053 Uiso 1 1 calc R U . . .
C14 C 0.2742(2) 0.36573(13) 0.6886(2) 0.0486(5) Uani 1 1 d . . . . .
C7 C 0.4148(2) 0.33020(13) 0.4873(2) 0.0491(5) Uani 1 1 d . . . . .
H7 H 0.426615 0.299720 0.395979 0.059 Uiso 1 1 calc R U . . .
C2 C 0.5982(2) 0.33300(13) 0.2229(2) 0.0509(5) Uani 1 1 d . . . . .
H2A H 0.518180 0.371442 0.205107 0.061 Uiso 1 1 calc R U . . .
H2B H 0.565806 0.273843 0.234586 0.061 Uiso 1 1 calc R U . . .
C9 C 0.2931(2) 0.32076(14) 0.5517(3) 0.0543(5) Uani 1 1 d . . . . .
H9 H 0.223187 0.284485 0.504487 0.065 Uiso 1 1 calc R U . . .
C5 C 0.8355(2) 0.36640(16) 0.3228(3) 0.0591(6) Uani 1 1 d . . . . .
H5A H 0.900518 0.339075 0.403149 0.071 Uiso 1 1 calc R U . . .
H5B H 0.862597 0.426663 0.311292 0.071 Uiso 1 1 calc R U . . .
C11 C 0.6879(3) 0.33940(15) 0.0903(3) 0.0627(6) Uani 1 1 d . . . . .
H11A H 0.658138 0.297941 0.007608 0.075 Uiso 1 1 calc R U . . .
H11B H 0.684712 0.397581 0.045965 0.075 Uiso 1 1 calc R U . . .
C3 C 0.8281(2) 0.54342(17) 0.8200(3) 0.0661(6) Uani 1 1 d . . . . .
H3A H 0.866638 0.583237 0.750287 0.099 Uiso 1 1 calc R U . . .
H3B H 0.901220 0.507831 0.872041 0.099 Uiso 1 1 calc R U . . .
H3C H 0.784347 0.575568 0.896872 0.099 Uiso 1 1 calc R U . . .
C13 C 0.8309(3) 0.31816(17) 0.1681(3) 0.0702(7) Uani 1 1 d . . . . .
H13A H 0.902311 0.339101 0.106671 0.084 Uiso 1 1 calc R U . . .
H13B H 0.842483 0.255977 0.184608 0.084 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 C14 1.744(2) . ?
N1 C1 1.363(2) . ?
N1 C8 1.316(2) . ?
N2 C6 1.362(2) . ?
N2 C2 1.469(2) . ?
N2 C5 1.464(3) . ?
C1 C4 1.420(2) . ?
C1 C10 1.414(3) . ?
C4 C6 1.446(2) . ?
C4 C7 1.416(3) . ?
C6 C12 1.386(2) . ?
C8 C12 1.391(3) . ?
C8 C3 1.505(3) . ?
C10 H10 0.9300 . ?
C10 C14 1.355(3) . ?
C12 H12 0.9300 . ?
C14 C9 1.391(3) . ?
C7 H7 0.9300 . ?
C7 C9 1.364(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C11 1.511(3) . ?
C9 H9 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C13 1.514(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C13 1.497(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
C8 N1 C1 116.46(16) . . ?
C6 N2 C2 127.69(16) . . ?
C6 N2 C5 120.25(16) . . ?
C5 N2 C2 110.08(15) . . ?
N1 C1 C4 124.41(16) . . ?
N1 C1 C10 115.69(16) . . ?
C10 C1 C4 119.89(16) . . ?
C1 C4 C6 117.36(15) . . ?
C7 C4 C1 116.95(17) . . ?
C7 C4 C6 125.58(17) . . ?
N2 C6 C4 124.21(16) . . ?
N2 C6 C12 119.94(17) . . ?
C12 C6 C4 115.81(16) . . ?
N1 C8 C12 124.00(17) . . ?
N1 C8 C3 116.34(17) . . ?
C12 C8 C3 119.64(18) . . ?
C1 C10 H10 119.9 . . ?
C14 C10 C1 120.16(18) . . ?
C14 C10 H10 119.9 . . ?
C6 C12 C8 121.82(17) . . ?
C6 C12 H12 119.1 . . ?
C8 C12 H12 119.1 . . ?
C10 C14 Cl1 120.41(16) . . ?
C10 C14 C9 121.22(19) . . ?
C9 C14 Cl1 118.36(15) . . ?
C4 C7 H7 118.9 . . ?
C9 C7 C4 122.13(19) . . ?
C9 C7 H7 118.9 . . ?
N2 C2 H2A 111.0 . . ?
N2 C2 H2B 111.0 . . ?
N2 C2 C11 103.66(17) . . ?
H2A C2 H2B 109.0 . . ?
C11 C2 H2A 111.0 . . ?
C11 C2 H2B 111.0 . . ?
C14 C9 H9 120.2 . . ?
C7 C9 C14 119.59(18) . . ?
C7 C9 H9 120.2 . . ?
N2 C5 H5A 111.0 . . ?
N2 C5 H5B 111.0 . . ?
N2 C5 C13 103.76(18) . . ?
H5A C5 H5B 109.0 . . ?
C13 C5 H5A 111.0 . . ?
C13 C5 H5B 111.0 . . ?
C2 C11 H11A 111.1 . . ?
C2 C11 H11B 111.1 . . ?
H11A C11 H11B 109.0 . . ?
C13 C11 C2 103.40(18) . . ?
C13 C11 H11A 111.1 . . ?
C13 C11 H11B 111.1 . . ?
C8 C3 H3A 109.5 . . ?
C8 C3 H3B 109.5 . . ?
C8 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C13 H13A 111.3 . . ?
C5 C13 H13B 111.3 . . ?
C11 C13 C5 102.28(18) . . ?
C11 C13 H13A 111.3 . . ?
C11 C13 H13B 111.3 . . ?
H13A C13 H13B 109.2 . . ?

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
Cl1 C14 C9 C7 178.03(16) . . . . ?
N1 C1 C4 C6 0.4(2) . . . . ?
N1 C1 C4 C7 176.88(16) . . . . ?
N1 C1 C10 C14 -178.63(16) . . . . ?
N1 C8 C12 C6 2.1(3) . . . . ?
N2 C6 C12 C8 178.28(17) . . . . ?
N2 C2 C11 C13 31.9(2) . . . . ?
N2 C5 C13 C11 34.6(2) . . . . ?
C1 N1 C8 C12 1.3(3) . . . . ?
C1 N1 C8 C3 180.00(17) . . . . ?
C1 C4 C6 N2 -179.62(16) . . . . ?
C1 C4 C6 C12 2.8(2) . . . . ?
C1 C4 C7 C9 2.0(3) . . . . ?
C1 C10 C14 Cl1 -178.20(14) . . . . ?
C1 C10 C14 C9 1.4(3) . . . . ?
C4 C1 C10 C14 0.5(3) . . . . ?
C4 C6 C12 C8 -4.0(3) . . . . ?
C4 C7 C9 C14 -0.2(3) . . . . ?
C6 N2 C2 C11 153.59(18) . . . . ?
C6 N2 C5 C13 179.64(18) . . . . ?
C6 C4 C7 C9 178.22(18) . . . . ?
C8 N1 C1 C4 -2.5(2) . . . . ?
C8 N1 C1 C10 176.62(16) . . . . ?
C10 C1 C4 C6 -178.68(15) . . . . ?
C10 C1 C4 C7 -2.2(2) . . . . ?
C10 C14 C9 C7 -1.6(3) . . . . ?
C7 C4 C6 N2 4.2(3) . . . . ?
C7 C4 C6 C12 -173.34(17) . . . . ?
C2 N2 C6 C4 25.6(3) . . . . ?
C2 N2 C6 C12 -156.90(18) . . . . ?
C2 N2 C5 C13 -15.2(2) . . . . ?
C2 C11 C13 C5 -41.2(2) . . . . ?
C5 N2 C6 C4 -172.03(17) . . . . ?
C5 N2 C6 C12 5.4(3) . . . . ?
C5 N2 C2 C11 -10.2(2) . . . . ?
C3 C8 C12 C6 -176.59(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
