# Supplementary Information (SI) for ChemComm.
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 2549327'
loop_
_audit_author_name
_audit_author_address
'Liangce Rong'
;Jiangsu normal university
China
;
_audit_update_record             
;
2026-04-25 deposited with the CCDC.	2026-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Br Cl I N O'
_chemical_formula_weight         528.60

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'
I I -0.4742 1.8119 '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'
Br Br -0.2901 2.4595 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0394(10)
_cell_length_b                   10.3187(10)
_cell_length_c                   18.7993(19)
_cell_angle_alpha                90
_cell_angle_beta                 96.115(5)
_cell_angle_gamma                90
_cell_volume                     1936.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9760
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      27.93

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    3.863
_shelx_estimated_absorpt_T_min   0.498
_shelx_estimated_absorpt_T_max   0.543
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38871
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.040
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_full        25.007
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3410
_reflns_number_gt                3176
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0380P)²+6.0940P] 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         3410
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
O1 O 0.5216(3) 0.3618(3) 0.32047(16) 0.0421(7) Uani 1 1 d . . . . .
N1 N 0.5704(3) 0.5755(3) 0.33564(17) 0.0316(7) Uani 1 1 d . . . . .
Cl1 Cl 0.76377(14) 0.57942(11) 0.58829(6) 0.0533(3) Uani 1 1 d . . . . .
Br1 Br 0.63022(6) -0.07534(5) 0.62991(3) 0.05745(16) Uani 1 1 d . . . . .
I1 I 1.00192(3) 0.18082(3) 0.30212(2) 0.06324(15) Uani 1 1 d . . . . .
C1 C 0.5980(4) 0.4466(4) 0.34463(19) 0.0288(8) Uani 1 1 d . . . . .
C2 C 0.7328(4) 0.4176(3) 0.38624(19) 0.0266(7) Uani 1 1 d . . . . .
C3 C 0.7476(3) 0.5067(3) 0.45030(19) 0.0270(7) Uani 1 1 d . . . . .
C4 C 0.7506(4) 0.6421(4) 0.4245(2) 0.0305(8) Uani 1 1 d . . . . .
C5 C 0.8371(4) 0.7381(4) 0.4534(3) 0.0436(10) Uani 1 1 d . . . . .
H5 H 0.896577 0.720125 0.493519 0.052 Uiso 1 1 calc R U . . .
C6 C 0.8359(5) 0.8602(5) 0.4229(3) 0.0579(13) Uani 1 1 d . . . . .
H6 H 0.893716 0.924050 0.442807 0.070 Uiso 1 1 calc R U . . .
C7 C 0.7489(5) 0.8868(5) 0.3634(3) 0.0570(13) Uani 1 1 d . . . . .
H7 H 0.748741 0.968897 0.342945 0.068 Uiso 1 1 calc R U . . .
C8 C 0.6619(5) 0.7936(4) 0.3334(3) 0.0454(10) Uani 1 1 d . . . . .
H8 H 0.603451 0.812633 0.292937 0.055 Uiso 1 1 calc R U . . .
C9 C 0.6622(4) 0.6714(4) 0.3640(2) 0.0314(8) Uani 1 1 d . . . . .
C10 C 0.4454(4) 0.6137(4) 0.2940(2) 0.0389(9) Uani 1 1 d . . . . .
H10A H 0.463229 0.638092 0.246646 0.058 Uiso 1 1 calc R U . . .
H10B H 0.406982 0.685828 0.316763 0.058 Uiso 1 1 calc R U . . .
H10C H 0.383863 0.542199 0.291198 0.058 Uiso 1 1 calc R U . . .
C11 C 0.8438(4) 0.4330(4) 0.3334(2) 0.0348(9) Uani 1 1 d . . . . .
H11A H 0.817847 0.488136 0.292492 0.042 Uiso 1 1 calc R U . . .
H11B H 0.931439 0.456452 0.356602 0.042 Uiso 1 1 calc R U . . .
C12 C 0.8262(4) 0.2883(4) 0.3183(2) 0.0347(8) Uani 1 1 d . . . . .
H12 H 0.757506 0.274891 0.277813 0.042 Uiso 1 1 calc R U . . .
C13 C 0.7648(4) 0.2708(4) 0.3887(2) 0.0329(8) Uani 1 1 d . . . . .
H13A H 0.828708 0.245301 0.428606 0.039 Uiso 1 1 calc R U . . .
H13B H 0.686152 0.215644 0.385046 0.039 Uiso 1 1 calc R U . . .
C14 C 0.7459(4) 0.4675(4) 0.5175(2) 0.0306(8) Uani 1 1 d . . . . .
C15 C 0.7208(4) 0.3345(4) 0.54281(19) 0.0298(8) Uani 1 1 d . . . . .
C16 C 0.5993(4) 0.2745(4) 0.5225(2) 0.0332(8) Uani 1 1 d . . . . .
H16 H 0.535284 0.316538 0.491368 0.040 Uiso 1 1 calc R U . . .
C17 C 0.5720(4) 0.1526(4) 0.5481(2) 0.0368(9) Uani 1 1 d . . . . .
H17 H 0.489978 0.112817 0.534715 0.044 Uiso 1 1 calc R U . . .
C18 C 0.6690(4) 0.0909(4) 0.5940(2) 0.0367(9) Uani 1 1 d . . . . .
C19 C 0.7900(4) 0.1486(4) 0.6144(2) 0.0410(10) Uani 1 1 d . . . . .
H19 H 0.854627 0.105430 0.644691 0.049 Uiso 1 1 calc R U . . .
C20 C 0.8152(4) 0.2706(4) 0.5900(2) 0.0368(9) Uani 1 1 d . . . . .
H20 H 0.896055 0.311043 0.605088 0.044 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
O1 C1 1.219(5) . ?
N1 C1 1.365(5) . ?
N1 C9 1.417(5) . ?
N1 C10 1.461(5) . ?
Cl1 C14 1.757(4) . ?
Br1 C18 1.899(4) . ?
I1 C12 2.133(4) . ?
C1 C2 1.519(5) . ?
C2 C3 1.510(5) . ?
C2 C13 1.548(5) . ?
C2 C11 1.578(5) . ?
C3 C14 1.328(5) . ?
C3 C4 1.480(5) . ?
C4 C5 1.390(6) . ?
C4 C9 1.400(5) . ?
C5 C6 1.383(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.386(6) . ?
C8 H8 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.527(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.530(5) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.483(5) . ?
C15 C16 1.385(6) . ?
C15 C20 1.393(5) . ?
C16 C17 1.384(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(6) . ?
C19 C20 1.373(6) . ?
C19 H19 0.9300 . ?
C20 H20 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
C1 N1 C9 121.2(3) . . ?
C1 N1 C10 118.7(3) . . ?
C9 N1 C10 120.0(3) . . ?
O1 C1 N1 122.8(3) . . ?
O1 C1 C2 122.7(3) . . ?
N1 C1 C2 114.4(3) . . ?
C3 C2 C1 107.3(3) . . ?
C3 C2 C13 124.7(3) . . ?
C1 C2 C13 112.3(3) . . ?
C3 C2 C11 115.1(3) . . ?
C1 C2 C11 107.8(3) . . ?
C13 C2 C11 87.7(3) . . ?
C14 C3 C4 127.0(3) . . ?
C14 C3 C2 124.2(3) . . ?
C4 C3 C2 108.5(3) . . ?
C5 C4 C9 118.6(4) . . ?
C5 C4 C3 125.4(4) . . ?
C9 C4 C3 115.9(3) . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 119.8(4) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 121.0(4) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C9 119.4(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C4 120.5(4) . . ?
C8 C9 N1 120.5(4) . . ?
C4 C9 N1 119.0(3) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C2 86.7(3) . . ?
C12 C11 H11A 114.2 . . ?
C2 C11 H11A 114.2 . . ?
C12 C11 H11B 114.2 . . ?
C2 C11 H11B 114.2 . . ?
H11A C11 H11B 111.4 . . ?
C11 C12 C13 90.2(3) . . ?
C11 C12 I1 117.0(3) . . ?
C13 C12 I1 118.5(3) . . ?
C11 C12 H12 109.9 . . ?
C13 C12 H12 109.9 . . ?
I1 C12 H12 109.9 . . ?
C12 C13 C2 87.7(3) . . ?
C12 C13 H13A 114.0 . . ?
C2 C13 H13A 114.0 . . ?
C12 C13 H13B 114.0 . . ?
C2 C13 H13B 114.0 . . ?
H13A C13 H13B 111.2 . . ?
C3 C14 C15 127.4(3) . . ?
C3 C14 Cl1 120.6(3) . . ?
C15 C14 Cl1 111.8(3) . . ?
C16 C15 C20 118.9(4) . . ?
C16 C15 C14 120.0(3) . . ?
C20 C15 C14 121.0(4) . . ?
C17 C16 C15 120.8(4) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 118.8(4) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C19 C18 C17 121.2(4) . . ?
C19 C18 Br1 120.2(3) . . ?
C17 C18 Br1 118.6(3) . . ?
C18 C19 C20 119.6(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C15 120.7(4) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?

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
C9 N1 C1 O1 -179.4(3) . . . . ?
C10 N1 C1 O1 -1.4(6) . . . . ?
C9 N1 C1 C2 -0.3(5) . . . . ?
C10 N1 C1 C2 177.7(3) . . . . ?
O1 C1 C2 C3 -136.1(4) . . . . ?
N1 C1 C2 C3 44.8(4) . . . . ?
O1 C1 C2 C13 4.5(5) . . . . ?
N1 C1 C2 C13 -174.6(3) . . . . ?
O1 C1 C2 C11 99.4(4) . . . . ?
N1 C1 C2 C11 -79.7(4) . . . . ?
C1 C2 C3 C14 110.9(4) . . . . ?
C13 C2 C3 C14 -23.5(6) . . . . ?
C11 C2 C3 C14 -129.1(4) . . . . ?
C1 C2 C3 C4 -63.7(4) . . . . ?
C13 C2 C3 C4 162.0(3) . . . . ?
C11 C2 C3 C4 56.4(4) . . . . ?
C14 C3 C4 C5 48.6(6) . . . . ?
C2 C3 C4 C5 -137.1(4) . . . . ?
C14 C3 C4 C9 -134.7(4) . . . . ?
C2 C3 C4 C9 39.7(4) . . . . ?
C9 C4 C5 C6 0.2(6) . . . . ?
C3 C4 C5 C6 176.8(4) . . . . ?
C4 C5 C6 C7 -0.5(8) . . . . ?
C5 C6 C7 C8 0.3(8) . . . . ?
C6 C7 C8 C9 0.1(8) . . . . ?
C7 C8 C9 C4 -0.4(6) . . . . ?
C7 C8 C9 N1 177.7(4) . . . . ?
C5 C4 C9 C8 0.3(6) . . . . ?
C3 C4 C9 C8 -176.7(4) . . . . ?
C5 C4 C9 N1 -177.9(4) . . . . ?
C3 C4 C9 N1 5.2(5) . . . . ?
C1 N1 C9 C8 154.7(4) . . . . ?
C10 N1 C9 C8 -23.3(5) . . . . ?
C1 N1 C9 C4 -27.1(5) . . . . ?
C10 N1 C9 C4 154.8(4) . . . . ?
C3 C2 C11 C12 148.2(3) . . . . ?
C1 C2 C11 C12 -92.1(3) . . . . ?
C13 C2 C11 C12 20.6(3) . . . . ?
C2 C11 C12 C13 -20.8(3) . . . . ?
C2 C11 C12 I1 -143.3(3) . . . . ?
C11 C12 C13 C2 21.2(3) . . . . ?
I1 C12 C13 C2 142.4(3) . . . . ?
C3 C2 C13 C12 -139.7(4) . . . . ?
C1 C2 C13 C12 87.8(3) . . . . ?
C11 C2 C13 C12 -20.5(3) . . . . ?
C4 C3 C14 C15 169.2(4) . . . . ?
C2 C3 C14 C15 -4.3(6) . . . . ?
C4 C3 C14 Cl1 -6.4(6) . . . . ?
C2 C3 C14 Cl1 -179.9(3) . . . . ?
C3 C14 C15 C16 -61.5(5) . . . . ?
Cl1 C14 C15 C16 114.4(3) . . . . ?
C3 C14 C15 C20 121.9(4) . . . . ?
Cl1 C14 C15 C20 -62.2(4) . . . . ?
C20 C15 C16 C17 -0.5(6) . . . . ?
C14 C15 C16 C17 -177.2(3) . . . . ?
C15 C16 C17 C18 -0.5(6) . . . . ?
C16 C17 C18 C19 0.3(6) . . . . ?
C16 C17 C18 Br1 179.2(3) . . . . ?
C17 C18 C19 C20 1.0(6) . . . . ?
Br1 C18 C19 C20 -177.9(3) . . . . ?
C18 C19 C20 C15 -2.1(6) . . . . ?
C16 C15 C20 C19 1.9(6) . . . . ?
C14 C15 C20 C19 178.6(4) . . . . ?

_refine_diff_density_max         1.062
_refine_diff_density_min         -1.776
_refine_diff_density_rms         0.114

