# Supplementary Information (SI) for RSC Advances.
# 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_cj129
_audit_block_doi                 10.5517/ccdc.csd.cc2p6qh4
_database_code_depnum_ccdc_archive 'CCDC 2479116'
loop_
_audit_author_name
_audit_author_address
'Claudio Jimenez'
;Universidad de Concepcion
Chile
;
_audit_update_record             
;
2025-08-07 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;

_audit_creation_date             2025-07-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 Cl N3 O'
_chemical_formula_sum            'C14 H10 Cl N3 O'
_chemical_formula_weight         271.70
_chemical_absolute_configuration .
_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           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                   9.2405(2)
_cell_length_b                   20.5457(5)
_cell_length_c                   6.9132(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.9410(10)
_cell_angle_gamma                90
_cell_volume                     1233.80(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7130
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1011 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.9595.
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    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            23549
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.345
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2156
_reflns_number_total             2520
_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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2520
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0664P)²+0.2691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1182
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C14(H14), C13(H13), C12(H12), C7(H7), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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 1.05083(5) 0.62619(2) 0.90168(8) 0.05563(19) Uani 1 1 d . . . . .
O1 O 0.69772(18) 0.48111(6) 0.7060(2) 0.0649(4) Uani 1 1 d . . . . .
N3 N 0.82696(15) 0.70800(6) 0.7821(2) 0.0367(3) Uani 1 1 d . . . . .
N1 N 0.61263(15) 0.78303(6) 0.6673(2) 0.0356(3) Uani 1 1 d . . . . .
N2 N 0.45302(16) 0.77821(7) 0.5801(2) 0.0425(3) Uani 1 1 d . . . . .
C9 C 0.68066(18) 0.84602(7) 0.7057(2) 0.0345(3) Uani 1 1 d . . . . .
C6 C 0.5929(2) 0.61191(8) 0.6522(2) 0.0379(4) Uani 1 1 d . . . . .
H6 H 0.516525 0.580331 0.608016 0.045 Uiso 1 1 calc R U . . .
C2 C 0.55558(18) 0.67753(8) 0.6346(2) 0.0360(3) Uani 1 1 d . . . . .
C3 C 0.67679(18) 0.72260(7) 0.7014(2) 0.0330(3) Uani 1 1 d . . . . .
C5 C 0.74642(19) 0.59450(7) 0.7372(2) 0.0377(4) Uani 1 1 d . . . . .
C14 C 0.5862(2) 0.90045(8) 0.6716(3) 0.0424(4) Uani 1 1 d . . . . .
H14 H 0.479716 0.895710 0.624049 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6513(2) 0.96151(8) 0.7089(3) 0.0484(4) Uani 1 1 d . . . . .
H13 H 0.588160 0.997983 0.686695 0.058 Uiso 1 1 calc R U . . .
C4 C 0.85577(19) 0.64531(8) 0.7969(2) 0.0369(3) Uani 1 1 d . . . . .
C1 C 0.41936(19) 0.71598(8) 0.5607(3) 0.0420(4) Uani 1 1 d . . . . .
C12 C 0.8093(2) 0.96930(9) 0.7788(3) 0.0492(4) Uani 1 1 d . . . . .
H12 H 0.852435 1.010701 0.802950 0.059 Uiso 1 1 calc R U . . .
C7 C 0.7886(2) 0.52489(8) 0.7607(3) 0.0471(4) Uani 1 1 d . . . . .
H7 H 0.892086 0.514299 0.821638 0.057 Uiso 1 1 calc R U . . .
C10 C 0.8393(2) 0.85318(8) 0.7766(3) 0.0427(4) Uani 1 1 d . . . . .
H10 H 0.902948 0.816819 0.799945 0.051 Uiso 1 1 calc R U . . .
C11 C 0.9020(2) 0.91506(9) 0.8122(3) 0.0493(4) Uani 1 1 d . . . . .
H11 H 1.008436 0.920077 0.859388 0.059 Uiso 1 1 calc R U . . .
C8 C 0.2569(2) 0.69289(11) 0.4728(4) 0.0659(6) Uani 1 1 d . . . . .
H8A H 0.228933 0.671103 0.577727 0.099 Uiso 1 1 calc R U . . .
H8B H 0.247326 0.663248 0.361739 0.099 Uiso 1 1 calc R U . . .
H8C H 0.189976 0.729453 0.422292 0.099 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 C4 1.7428(17) . ?
O1 C7 1.200(2) . ?
N3 C3 1.341(2) . ?
N3 C4 1.312(2) . ?
N1 N2 1.3936(19) . ?
N1 C9 1.4237(19) . ?
N1 C3 1.3612(19) . ?
N2 C1 1.312(2) . ?
C9 C14 1.388(2) . ?
C9 C10 1.386(2) . ?
C6 H6 0.9300 . ?
C6 C2 1.387(2) . ?
C6 C5 1.385(2) . ?
C2 C3 1.404(2) . ?
C2 C1 1.425(2) . ?
C5 C4 1.413(2) . ?
C5 C7 1.477(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.377(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.381(3) . ?
C1 C8 1.492(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.377(3) . ?
C7 H7 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.384(2) . ?
C11 H11 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C4 N3 C3 113.93(13) . . ?
N2 N1 C9 118.69(12) . . ?
C3 N1 N2 110.14(12) . . ?
C3 N1 C9 131.17(14) . . ?
C1 N2 N1 107.00(13) . . ?
C14 C9 N1 119.24(15) . . ?
C10 C9 N1 120.59(14) . . ?
C10 C9 C14 120.17(15) . . ?
C2 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C5 C6 C2 118.45(15) . . ?
C6 C2 C3 117.77(15) . . ?
C6 C2 C1 137.15(15) . . ?
C3 C2 C1 105.08(14) . . ?
N3 C3 N1 127.14(14) . . ?
N3 C3 C2 125.82(14) . . ?
N1 C3 C2 107.04(13) . . ?
C6 C5 C4 117.40(14) . . ?
C6 C5 C7 119.37(15) . . ?
C4 C5 C7 123.22(16) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 C9 119.50(17) . . ?
C13 C14 H14 120.2 . . ?
C14 C13 H13 119.6 . . ?
C14 C13 C12 120.89(17) . . ?
C12 C13 H13 119.6 . . ?
N3 C4 Cl1 114.03(12) . . ?
N3 C4 C5 126.62(16) . . ?
C5 C4 Cl1 119.34(12) . . ?
N2 C1 C2 110.73(15) . . ?
N2 C1 C8 121.48(17) . . ?
C2 C1 C8 127.79(16) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 C13 119.21(16) . . ?
C11 C12 H12 120.4 . . ?
O1 C7 C5 124.15(18) . . ?
O1 C7 H7 117.9 . . ?
C5 C7 H7 117.9 . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.24(16) . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 121.00(18) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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 C1 C2 0.07(19) . . . . ?
N1 N2 C1 C8 179.66(17) . . . . ?
N1 C9 C14 C13 179.88(15) . . . . ?
N1 C9 C10 C11 179.90(15) . . . . ?
N2 N1 C9 C14 5.3(2) . . . . ?
N2 N1 C9 C10 -174.75(14) . . . . ?
N2 N1 C3 N3 179.61(14) . . . . ?
N2 N1 C3 C2 -0.02(17) . . . . ?
C9 N1 N2 C1 -179.92(14) . . . . ?
C9 N1 C3 N3 -0.5(3) . . . . ?
C9 N1 C3 C2 179.85(14) . . . . ?
C9 C14 C13 C12 0.3(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C6 C2 C3 N3 -0.2(2) . . . . ?
C6 C2 C3 N1 179.43(13) . . . . ?
C6 C2 C1 N2 -179.26(18) . . . . ?
C6 C2 C1 C8 1.2(3) . . . . ?
C6 C5 C4 Cl1 -179.18(12) . . . . ?
C6 C5 C4 N3 0.7(2) . . . . ?
C6 C5 C7 O1 1.8(3) . . . . ?
C2 C6 C5 C4 -1.2(2) . . . . ?
C2 C6 C5 C7 178.98(14) . . . . ?
C3 N3 C4 Cl1 179.99(11) . . . . ?
C3 N3 C4 C5 0.1(2) . . . . ?
C3 N1 N2 C1 -0.03(18) . . . . ?
C3 N1 C9 C14 -174.52(15) . . . . ?
C3 N1 C9 C10 5.4(3) . . . . ?
C3 C2 C1 N2 -0.08(18) . . . . ?
C3 C2 C1 C8 -179.64(19) . . . . ?
C5 C6 C2 C3 1.0(2) . . . . ?
C5 C6 C2 C1 -179.87(18) . . . . ?
C14 C9 C10 C11 -0.2(2) . . . . ?
C14 C13 C12 C11 -0.3(3) . . . . ?
C13 C12 C11 C10 0.1(3) . . . . ?
C4 N3 C3 N1 -179.93(14) . . . . ?
C4 N3 C3 C2 -0.4(2) . . . . ?
C4 C5 C7 O1 -178.00(18) . . . . ?
C1 C2 C3 N3 -179.58(15) . . . . ?
C1 C2 C3 N1 0.06(16) . . . . ?
C7 C5 C4 Cl1 0.6(2) . . . . ?
C7 C5 C4 N3 -179.53(16) . . . . ?
C10 C9 C14 C13 0.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'



