# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2392817'
loop_
_audit_author_name
_audit_author_address
'He Zhao'
;Yancheng Institute of Technology
China
;
_audit_update_record             
;
2024-10-22 deposited with the CCDC.	2026-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H19 Cl F2 I2 N4'
_chemical_formula_weight         786.76

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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

_cell_length_a                   4.770(5)
_cell_length_b                   21.58(2)
_cell_length_c                   13.886(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.751(18)
_cell_angle_gamma                90
_cell_volume                     1416(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1110
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      20.83

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.358
_shelx_estimated_absorpt_T_min   0.625
_shelx_estimated_absorpt_T_max   0.676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5264
_diffrn_reflns_av_unetI/netI     0.1302
_diffrn_reflns_av_R_equivalents  0.1053
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.755
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             2425
_reflns_number_gt                1622
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1698P)²+5.9124P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2425
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1473
_refine_ls_R_factor_gt           0.1034
_refine_ls_wR_factor_ref         0.3078
_refine_ls_wR_factor_gt          0.2795
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_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_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
I1 I -0.1602(3) 1.00781(5) 0.85552(8) 0.0750(6) Uani 1 1 d . . . . .
N1 N 0.116(2) 0.8640(4) 0.4906(7) 0.037(2) Uani 1 1 d . . . . .
N2 N 0.458(2) 0.7820(4) 0.4824(7) 0.040(2) Uani 1 1 d . . . . .
C1 C 0.027(2) 0.8986(5) 0.5631(8) 0.035(3) Uani 1 1 d . . . . .
C2 C -0.185(3) 0.9452(5) 0.5550(9) 0.042(3) Uani 1 1 d . . . . .
H2B H -0.2855 0.9557 0.4951 0.051 Uiso 1 1 calc R U . . .
C3 C -0.238(3) 0.9749(6) 0.6415(10) 0.046(3) Uani 1 1 d . . . . .
H3A H -0.3814 1.0042 0.6396 0.055 Uiso 1 1 calc R U . . .
C4 C -0.074(3) 0.9601(5) 0.7306(9) 0.040(3) Uani 1 1 d . . . . .
C5 C 0.134(3) 0.9150(5) 0.7380(9) 0.035(3) Uani 1 1 d . . . . .
H5A H 0.2376 0.9058 0.7979 0.042 Uiso 1 1 calc R U . . .
C6 C 0.186(2) 0.8835(5) 0.6553(8) 0.030(2) Uani 1 1 d . . . . .
C7 C 0.377(2) 0.8347(5) 0.6337(8) 0.030(2) Uani 1 1 d . . . . .
C8 C 0.581(2) 0.7994(5) 0.6901(8) 0.030(2) Uani 1 1 d . . . . .
H8A H 0.6205 0.8053 0.7568 0.036 Uiso 1 1 calc R U . . .
C9 C 0.728(2) 0.7530(5) 0.6410(8) 0.031(2) Uani 1 1 d . . . . .
C10 C 0.939(3) 0.7137(5) 0.6946(9) 0.040(3) Uani 1 1 d . . . . .
H10A H 0.9852 0.7181 0.7615 0.048 Uiso 1 1 calc R U . . .
C11 C 1.070(3) 0.6698(6) 0.6449(10) 0.047(3) Uani 1 1 d . . . . .
H11A H 1.2044 0.6440 0.6789 0.057 Uiso 1 1 calc R U . . .
C12 C 1.005(3) 0.6632(5) 0.5455(11) 0.046(3) Uani 1 1 d . . . . .
H12 H 1.0974 0.6334 0.5130 0.056 Uiso 0.5 1 calc R U P A 1
Cl1 Cl 1.141(3) 0.6096(4) 0.4763(8) 0.099(3) Uani 0.5 1 d . . P B 2
C13 C 0.806(3) 0.7001(5) 0.4955(10) 0.050(4) Uani 1 1 d . . . . .
C14 C 0.655(2) 0.7456(4) 0.5399(9) 0.031(3) Uani 1 1 d . . . . .
C15 C 0.329(2) 0.8230(5) 0.5319(9) 0.033(3) Uani 1 1 d . . . . .
C16 C -0.011(3) 0.8611(7) 0.3857(10) 0.056(4) Uani 1 1 d . . . . .
H16A H 0.0955 0.8328 0.3516 0.084 Uiso 1 1 calc R U . . .
H16B H -0.2036 0.8472 0.3811 0.084 Uiso 1 1 calc R U . . .
H16C H -0.0065 0.9016 0.3573 0.084 Uiso 1 1 calc R U . . .
F1 F 0.755(2) 0.6938(4) 0.3967(7) 0.074(3) Uani 1 1 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
I1 C4 2.106(12) . ?
N1 C1 1.365(16) . ?
N1 C15 1.411(15) . ?
N1 C16 1.501(16) . ?
N2 C15 1.322(15) . ?
N2 C14 1.389(16) . ?
C1 C2 1.420(17) . ?
C1 C6 1.435(15) . ?
C2 C3 1.413(18) . ?
C3 C4 1.409(18) . ?
C4 C5 1.382(17) . ?
C5 C6 1.385(16) . ?
C6 C7 1.448(16) . ?
C7 C8 1.391(16) . ?
C7 C15 1.424(16) . ?
C8 C9 1.446(16) . ?
C9 C14 1.409(17) . ?
C9 C10 1.442(16) . ?
C10 C11 1.369(18) . ?
C11 C12 1.380(19) . ?
C12 C13 1.355(19) . ?
C12 Cl1 1.688(17) . ?
C13 F1 1.368(16) . ?
C13 C14 1.410(17) . ?

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
C1 N1 C15 108.7(9) . . ?
C1 N1 C16 127.8(11) . . ?
C15 N1 C16 122.9(10) . . ?
C15 N2 C14 113.8(10) . . ?
N1 C1 C2 128.1(11) . . ?
N1 C1 C6 110.8(10) . . ?
C2 C1 C6 121.1(11) . . ?
C1 C2 C3 117.4(12) . . ?
C4 C3 C2 120.1(12) . . ?
C5 C4 C3 122.2(12) . . ?
C5 C4 I1 120.1(9) . . ?
C3 C4 I1 117.7(9) . . ?
C6 C5 C4 119.4(11) . . ?
C5 C6 C1 119.7(11) . . ?
C5 C6 C7 135.7(11) . . ?
C1 C6 C7 104.6(9) . . ?
C8 C7 C15 117.9(10) . . ?
C8 C7 C6 133.8(10) . . ?
C15 C7 C6 108.3(10) . . ?
C7 C8 C9 117.5(10) . . ?
C14 C9 C10 120.7(10) . . ?
C14 C9 C8 118.4(10) . . ?
C10 C9 C8 120.9(10) . . ?
C11 C10 C9 118.6(12) . . ?
C10 C11 C12 121.3(12) . . ?
C13 C12 C11 119.9(12) . . ?
C13 C12 Cl1 114.0(12) . . ?
C11 C12 Cl1 126.1(12) . . ?
C12 C13 F1 118.3(12) . . ?
C12 C13 C14 123.3(13) . . ?
F1 C13 C14 118.4(12) . . ?
N2 C14 C9 124.6(10) . . ?
N2 C14 C13 119.2(11) . . ?
C9 C14 C13 116.1(11) . . ?
N2 C15 N1 124.7(11) . . ?
N2 C15 C7 127.7(11) . . ?
N1 C15 C7 107.6(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
C15 N1 C1 C2 -179.5(11) . . . . ?
C16 N1 C1 C2 -7.7(19) . . . . ?
C15 N1 C1 C6 2.2(12) . . . . ?
C16 N1 C1 C6 174.0(10) . . . . ?
N1 C1 C2 C3 -179.7(11) . . . . ?
C6 C1 C2 C3 -1.6(16) . . . . ?
C1 C2 C3 C4 3.1(17) . . . . ?
C2 C3 C4 C5 -2.8(19) . . . . ?
C2 C3 C4 I1 178.7(9) . . . . ?
C3 C4 C5 C6 0.8(17) . . . . ?
I1 C4 C5 C6 179.2(8) . . . . ?
C4 C5 C6 C1 0.8(15) . . . . ?
C4 C5 C6 C7 -179.6(11) . . . . ?
N1 C1 C6 C5 178.1(9) . . . . ?
C2 C1 C6 C5 -0.4(15) . . . . ?
N1 C1 C6 C7 -1.7(11) . . . . ?
C2 C1 C6 C7 179.9(10) . . . . ?
C5 C6 C7 C8 2(2) . . . . ?
C1 C6 C7 C8 -178.5(11) . . . . ?
C5 C6 C7 C15 -179.1(11) . . . . ?
C1 C6 C7 C15 0.5(11) . . . . ?
C15 C7 C8 C9 -0.2(14) . . . . ?
C6 C7 C8 C9 178.8(10) . . . . ?
C7 C8 C9 C14 -1.0(14) . . . . ?
C7 C8 C9 C10 -178.9(9) . . . . ?
C14 C9 C10 C11 1.1(16) . . . . ?
C8 C9 C10 C11 179.0(10) . . . . ?
C9 C10 C11 C12 0.6(18) . . . . ?
C10 C11 C12 C13 -0.8(19) . . . . ?
C10 C11 C12 Cl1 -177.7(11) . . . . ?
C11 C12 C13 F1 177.6(11) . . . . ?
Cl1 C12 C13 F1 -5.2(16) . . . . ?
C11 C12 C13 C14 -0.8(19) . . . . ?
Cl1 C12 C13 C14 176.5(10) . . . . ?
C15 N2 C14 C9 -4.0(14) . . . . ?
C15 N2 C14 C13 179.8(10) . . . . ?
C10 C9 C14 N2 -178.8(10) . . . . ?
C8 C9 C14 N2 3.3(15) . . . . ?
C10 C9 C14 C13 -2.5(14) . . . . ?
C8 C9 C14 C13 179.6(9) . . . . ?
C12 C13 C14 N2 178.9(11) . . . . ?
F1 C13 C14 N2 0.5(16) . . . . ?
C12 C13 C14 C9 2.4(17) . . . . ?
F1 C13 C14 C9 -175.9(10) . . . . ?
C14 N2 C15 N1 -178.1(10) . . . . ?
C14 N2 C15 C7 2.7(15) . . . . ?
C1 N1 C15 N2 178.9(10) . . . . ?
C16 N1 C15 N2 6.6(17) . . . . ?
C1 N1 C15 C7 -1.7(12) . . . . ?
C16 N1 C15 C7 -174.1(10) . . . . ?
C8 C7 C15 N2 -0.7(16) . . . . ?
C6 C7 C15 N2 -179.9(10) . . . . ?
C8 C7 C15 N1 180.0(9) . . . . ?
C6 C7 C15 N1 0.7(11) . . . . ?

_refine_diff_density_max         1.254
_refine_diff_density_min         -1.181
_refine_diff_density_rms         0.274

