# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_khc1991h
_database_code_depnum_ccdc_archive 'CCDC 2478275'
loop_
_audit_author_name
_audit_author_address
'Behrouz Notash'
;Shahid Beheshti University
Iran
;
_audit_update_record             
;
2025-08-03 deposited with the CCDC.	2025-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H12 Cl N3 O3, C3 H7 N O'
_chemical_formula_sum            'C24 H19 Cl N4 O4'
_chemical_formula_weight         462.88

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2bc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.683(3)
_cell_length_b                   8.7068(17)
_cell_length_c                   16.643(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.37(3)
_cell_angle_gamma                90.00
_cell_volume                     2307.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4046
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10979
_diffrn_reflns_av_R_equivalents  0.1615
_diffrn_reflns_av_sigmaI/netI    0.1572
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4046
_reflns_number_gt                1732
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0645P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4046
_refine_ls_number_parameters     306
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1995
_refine_ls_R_factor_gt           0.0843
_refine_ls_wR_factor_ref         0.1915
_refine_ls_wR_factor_gt          0.1579
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.969
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.11921(11) 1.1077(3) 0.37030(15) 0.1309(8) Uani 1 1 d . . .
O1 O 0.49993(19) 0.7845(3) 0.46971(17) 0.0517(8) Uani 1 1 d . . .
O2 O 0.7834(2) 0.3696(4) 0.7132(2) 0.0708(10) Uani 1 1 d . . .
O3 O 0.5371(2) 0.4423(4) 0.6954(2) 0.0694(10) Uani 1 1 d . . .
O4 O 1.0599(3) 0.5668(8) 0.3915(4) 0.155(3) Uani 1 1 d . . .
N1 N 0.7256(3) 0.8060(6) 0.3545(3) 0.0965(17) Uani 1 1 d . . .
N2 N 0.6283(2) 0.6487(4) 0.5201(2) 0.0528(10) Uani 1 1 d . . .
N3 N 0.7775(3) 0.5154(6) 0.6026(3) 0.0703(13) Uani 1 1 d D . .
N4 N 0.9701(3) 0.7618(7) 0.3782(4) 0.0988(17) Uani 1 1 d . . .
C1 C 0.2204(3) 1.0423(7) 0.3800(4) 0.0743(16) Uani 1 1 d . . .
C2 C 0.2621(4) 1.0949(6) 0.3265(3) 0.0709(15) Uani 1 1 d . . .
H2 H 0.2362 1.1635 0.2837 0.085 Uiso 1 1 calc R . .
C3 C 0.2570(4) 0.9400(7) 0.4423(4) 0.0756(16) Uani 1 1 d . . .
H3 H 0.2279 0.9058 0.4786 0.091 Uiso 1 1 calc R . .
C4 C 0.3363(3) 0.8880(6) 0.4512(3) 0.0630(14) Uani 1 1 d . . .
H4 H 0.3606 0.8163 0.4927 0.076 Uiso 1 1 calc R . .
C5 C 0.3421(3) 1.0462(6) 0.3360(3) 0.0607(14) Uani 1 1 d . . .
H5 H 0.3710 1.0833 0.3002 0.073 Uiso 1 1 calc R . .
C6 C 0.3810(3) 0.9414(5) 0.3989(3) 0.0528(12) Uani 1 1 d . . .
C7 C 0.4664(3) 0.8887(5) 0.4068(3) 0.0509(12) Uani 1 1 d . . .
C8 C 0.5201(3) 0.9159(5) 0.3628(3) 0.0555(13) Uani 1 1 d . . .
H8 H 0.5118 0.9821 0.3172 0.067 Uiso 1 1 calc R . .
C9 C 0.5917(3) 0.8252(6) 0.3988(3) 0.0528(12) Uani 1 1 d D . .
C10 C 0.5781(3) 0.7458(5) 0.4648(3) 0.0468(11) Uani 1 1 d . . .
C11 C 0.6656(3) 0.8128(6) 0.3750(3) 0.0686(15) Uani 1 1 d D . .
C12 C 0.6018(3) 0.5828(5) 0.5782(3) 0.0533(13) Uani 1 1 d . . .
H12 H 0.5466 0.6011 0.5775 0.064 Uiso 1 1 calc R . .
C13 C 0.6509(3) 0.4860(5) 0.6419(3) 0.0501(12) Uani 1 1 d . . .
C14 C 0.7352(4) 0.4587(6) 0.6516(3) 0.0588(13) Uani 1 1 d . . .
C15 C 0.7476(4) 0.2956(6) 0.7687(3) 0.0672(15) Uani 1 1 d . . .
C16 C 0.6635(4) 0.3159(6) 0.7628(3) 0.0629(14) Uani 1 1 d . . .
C17 C 0.6118(4) 0.4183(5) 0.6999(3) 0.0558(13) Uani 1 1 d . . .
C18 C 0.6331(4) 0.2300(6) 0.8186(3) 0.0773(17) Uani 1 1 d . . .
H18 H 0.5770 0.2383 0.8165 0.093 Uiso 1 1 calc R . .
C19 C 0.6850(6) 0.1342(8) 0.8763(4) 0.102(2) Uani 1 1 d . . .
H19 H 0.6636 0.0768 0.9123 0.122 Uiso 1 1 calc R . .
C20 C 0.7675(5) 0.1223(8) 0.8813(4) 0.100(2) Uani 1 1 d . . .
H20 H 0.8026 0.0591 0.9219 0.120 Uiso 1 1 calc R . .
C21 C 0.7995(4) 0.2027(7) 0.8271(4) 0.0902(19) Uani 1 1 d . . .
H21 H 0.8559 0.1939 0.8302 0.108 Uiso 1 1 calc R . .
C22 C 0.9254(4) 0.8910(9) 0.3308(6) 0.140(3) Uani 1 1 d . . .
H22A H 0.9378 0.9819 0.3649 0.210 Uiso 1 1 calc R . .
H22B H 0.8661 0.8712 0.3148 0.210 Uiso 1 1 calc R . .
H22C H 0.9426 0.9055 0.2812 0.210 Uiso 1 1 calc R . .
C23 C 0.9533(6) 0.7265(14) 0.4542(7) 0.219(6) Uani 1 1 d . . .
H23A H 0.8981 0.6828 0.4420 0.328 Uiso 1 1 calc R . .
H23B H 0.9562 0.8185 0.4867 0.328 Uiso 1 1 calc R . .
H23C H 0.9941 0.6541 0.4856 0.328 Uiso 1 1 calc R . .
C24 C 1.0238(5) 0.6796(12) 0.3555(6) 0.134(3) Uani 1 1 d . . .
H24 H 1.0360 0.7096 0.3069 0.160 Uiso 1 1 calc R . .
H3A H 0.749(5) 0.572(8) 0.567(4) 0.160 Uiso 1 1 d D . .
H3B H 0.822(3) 0.482(9) 0.607(5) 0.160 Uiso 1 1 d D . .


_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 1.743(6) . ?
O1 C7 1.371(5) . ?
O1 C10 1.374(5) . ?
O2 C14 1.345(6) . ?
O2 C15 1.399(6) . ?
O3 C17 1.245(6) . ?
O4 C24 1.212(9) . ?
N1 C11 1.152(6) . ?
N2 C12 1.311(5) . ?
N2 C10 1.343(5) . ?
N3 C14 1.323(7) . ?
N3 H3A 0.80(2) . ?
N3 H3B 0.78(2) . ?
N4 C24 1.288(9) . ?
N4 C23 1.408(8) . ?
N4 C22 1.447(8) . ?
C1 C2 1.363(7) . ?
C1 C3 1.364(7) . ?
C2 C5 1.364(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(7) . ?
C3 H3 0.9300 . ?
C4 C6 1.384(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.465(7) . ?
C7 C8 1.337(6) . ?
C8 C9 1.408(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(6) . ?
C9 C11 1.407(6) . ?
C12 C13 1.409(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(7) . ?
C13 C17 1.442(6) . ?
C15 C21 1.358(7) . ?
C15 C16 1.388(8) . ?
C16 C18 1.400(7) . ?
C16 C17 1.447(7) . ?
C18 C19 1.368(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.359(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.370(8) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24 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
C7 O1 C10 107.2(3) . . ?
C14 O2 C15 119.5(4) . . ?
C12 N2 C10 120.3(4) . . ?
C14 N3 H3A 112(6) . . ?
C14 N3 H3B 119(6) . . ?
H3A N3 H3B 128(8) . . ?
C24 N4 C23 119.0(8) . . ?
C24 N4 C22 124.2(7) . . ?
C23 N4 C22 116.8(7) . . ?
C2 C1 C3 121.1(5) . . ?
C2 C1 Cl1 119.9(5) . . ?
C3 C1 Cl1 119.0(5) . . ?
C1 C2 C5 119.5(5) . . ?
C1 C2 H2 120.3 . . ?
C5 C2 H2 120.3 . . ?
C4 C3 C1 119.9(5) . . ?
C4 C3 H3 120.0 . . ?
C1 C3 H3 120.0 . . ?
C3 C4 C6 120.4(5) . . ?
C3 C4 H4 119.8 . . ?
C6 C4 H4 119.8 . . ?
C2 C5 C6 120.8(5) . . ?
C2 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C4 C6 C5 118.3(5) . . ?
C4 C6 C7 122.0(5) . . ?
C5 C6 C7 119.7(4) . . ?
C8 C7 O1 110.3(4) . . ?
C8 C7 C6 133.5(4) . . ?
O1 C7 C6 116.1(4) . . ?
C7 C8 C9 106.9(4) . . ?
C7 C8 H8 126.6 . . ?
C9 C8 H8 126.6 . . ?
C10 C9 C11 123.7(5) . . ?
C10 C9 C8 107.5(4) . . ?
C11 C9 C8 128.8(4) . . ?
N2 C10 C9 130.4(4) . . ?
N2 C10 O1 121.5(4) . . ?
C9 C10 O1 108.1(4) . . ?
N1 C11 C9 178.3(6) . . ?
N2 C12 C13 124.6(5) . . ?
N2 C12 H12 117.7 . . ?
C13 C12 H12 117.7 . . ?
C14 C13 C12 122.2(4) . . ?
C14 C13 C17 119.8(5) . . ?
C12 C13 C17 118.0(5) . . ?
N3 C14 O2 112.1(5) . . ?
N3 C14 C13 124.9(5) . . ?
O2 C14 C13 122.9(5) . . ?
C21 C15 C16 122.8(6) . . ?
C21 C15 O2 116.1(6) . . ?
C16 C15 O2 121.1(5) . . ?
C15 C16 C18 116.3(5) . . ?
C15 C16 C17 120.0(5) . . ?
C18 C16 C17 123.7(5) . . ?
O3 C17 C13 122.5(5) . . ?
O3 C17 C16 121.0(5) . . ?
C13 C17 C16 116.5(5) . . ?
C19 C18 C16 120.9(6) . . ?
C19 C18 H18 119.5 . . ?
C16 C18 H18 119.5 . . ?
C20 C19 C18 120.4(7) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.5(7) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C15 C21 C20 119.0(7) . . ?
C15 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N4 C23 H23A 109.5 . . ?
N4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O4 C24 N4 126.3(9) . . ?
O4 C24 H24 116.9 . . ?
N4 C24 H24 116.9 . . ?

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
C3 C1 C2 C5 -0.9(8) . . . . ?
Cl1 C1 C2 C5 178.2(4) . . . . ?
C2 C1 C3 C4 -0.5(9) . . . . ?
Cl1 C1 C3 C4 -179.7(4) . . . . ?
C1 C3 C4 C6 1.7(8) . . . . ?
C1 C2 C5 C6 1.1(8) . . . . ?
C3 C4 C6 C5 -1.5(7) . . . . ?
C3 C4 C6 C7 179.7(5) . . . . ?
C2 C5 C6 C4 0.0(7) . . . . ?
C2 C5 C6 C7 178.9(5) . . . . ?
C10 O1 C7 C8 0.3(5) . . . . ?
C10 O1 C7 C6 177.8(4) . . . . ?
C4 C6 C7 C8 176.3(5) . . . . ?
C5 C6 C7 C8 -2.5(8) . . . . ?
C4 C6 C7 O1 -0.6(6) . . . . ?
C5 C6 C7 O1 -179.4(4) . . . . ?
O1 C7 C8 C9 0.0(5) . . . . ?
C6 C7 C8 C9 -177.0(5) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C7 C8 C9 C11 179.8(5) . . . . ?
C12 N2 C10 C9 -178.9(5) . . . . ?
C12 N2 C10 O1 3.1(6) . . . . ?
C11 C9 C10 N2 2.2(8) . . . . ?
C8 C9 C10 N2 -177.7(4) . . . . ?
C11 C9 C10 O1 -179.7(5) . . . . ?
C8 C9 C10 O1 0.5(5) . . . . ?
C7 O1 C10 N2 177.9(4) . . . . ?
C7 O1 C10 C9 -0.5(5) . . . . ?
C10 C9 C11 N1 -161(23) . . . . ?
C8 C9 C11 N1 19(24) . . . . ?
C10 N2 C12 C13 -176.3(4) . . . . ?
N2 C12 C13 C14 3.9(7) . . . . ?
N2 C12 C13 C17 -178.1(4) . . . . ?
C15 O2 C14 N3 -177.5(4) . . . . ?
C15 O2 C14 C13 2.4(7) . . . . ?
C12 C13 C14 N3 -1.6(8) . . . . ?
C17 C13 C14 N3 -179.6(5) . . . . ?
C12 C13 C14 O2 178.4(4) . . . . ?
C17 C13 C14 O2 0.5(7) . . . . ?
C14 O2 C15 C21 177.4(4) . . . . ?
C14 O2 C15 C16 -1.8(7) . . . . ?
C21 C15 C16 C18 -2.4(8) . . . . ?
O2 C15 C16 C18 176.7(4) . . . . ?
C21 C15 C16 C17 179.1(5) . . . . ?
O2 C15 C16 C17 -1.7(7) . . . . ?
C14 C13 C17 O3 178.1(5) . . . . ?
C12 C13 C17 O3 0.1(7) . . . . ?
C14 C13 C17 C16 -3.8(6) . . . . ?
C12 C13 C17 C16 178.1(4) . . . . ?
C15 C16 C17 O3 -177.4(5) . . . . ?
C18 C16 C17 O3 4.2(7) . . . . ?
C15 C16 C17 C13 4.4(6) . . . . ?
C18 C16 C17 C13 -173.9(5) . . . . ?
C15 C16 C18 C19 1.1(7) . . . . ?
C17 C16 C18 C19 179.5(5) . . . . ?
C16 C18 C19 C20 1.0(9) . . . . ?
C18 C19 C20 C21 -1.9(11) . . . . ?
C16 C15 C21 C20 1.7(8) . . . . ?
O2 C15 C21 C20 -177.6(5) . . . . ?
C19 C20 C21 C15 0.6(10) . . . . ?
C23 N4 C24 O4 3.8(14) . . . . ?
C22 N4 C24 O4 -176.7(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.049
