# 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 2524459'
loop_
_audit_author_name
_audit_author_address
'Bo Jiang' 'Jiangsu Normal University'
_audit_update_record             
;
2026-01-20 deposited with the CCDC.	2026-03-13 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            'C19 H13 Br I N O3'
_chemical_formula_weight         510.11

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.3319(3)
_cell_length_b                   9.4965(3)
_cell_length_c                   10.8223(4)
_cell_angle_alpha                100.5309(14)
_cell_angle_beta                 92.6979(16)
_cell_angle_gamma                106.8278(15)
_cell_volume                     897.44(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9821
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.94

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.888
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    4.028
_shelx_estimated_absorpt_T_min   0.500
_shelx_estimated_absorpt_T_max   0.565
_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            27254
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.293
_diffrn_reflns_theta_max         27.955
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4316
_reflns_number_gt                3968
_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    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0306P)²+2.9424P] 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         4316
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_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_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 0.68807(4) 0.35247(3) 0.53604(3) 0.05081(12) Uani 1 1 d . . . . .
O1 O 0.8018(3) 0.3714(3) 0.1632(2) 0.0381(6) Uani 1 1 d . . . . .
N1 N 0.6992(4) 0.1595(4) 0.2496(3) 0.0360(7) Uani 1 1 d . . . . .
C3 C 0.8052(4) 0.5505(4) 0.3436(4) 0.0318(7) Uani 1 1 d . . . . .
C5 C 0.8226(4) 0.6966(4) 0.4292(4) 0.0349(8) Uani 1 1 d . . . . .
C2 C 0.7564(4) 0.4142(4) 0.3701(3) 0.0320(7) Uani 1 1 d . . . . .
C1 C 0.7503(4) 0.2999(4) 0.2576(3) 0.0323(8) Uani 1 1 d . . . . .
C4 C 0.8440(5) 0.5317(4) 0.2093(4) 0.0357(8) Uani 1 1 d . . . . .
C6 C 0.9235(5) 0.7437(5) 0.5367(4) 0.0458(10) Uani 1 1 d . . . . .
H6 H 0.984426 0.685929 0.553490 0.055 Uiso 1 1 calc R U . . .
C7 C 0.9343(6) 0.8770(6) 0.6197(5) 0.0579(13) Uani 1 1 d . . . . .
H7 H 1.002893 0.908637 0.691794 0.069 Uiso 1 1 calc R U . . .
C16 C 0.5683(4) -0.0806(4) 0.1227(3) 0.0311(7) Uani 1 1 d . . . . .
C11 C 0.6883(4) 0.0524(4) 0.1384(3) 0.0311(7) Uani 1 1 d . . . . .
C12 C 0.7923(5) 0.0650(5) 0.0493(4) 0.0407(9) Uani 1 1 d . . . . .
H12 H 0.872841 0.152417 0.058696 0.049 Uiso 1 1 calc R U . . .
C13 C 0.7763(5) -0.0516(5) -0.0529(4) 0.0428(9) Uani 1 1 d . . . . .
H13 H 0.846875 -0.043236 -0.111217 0.051 Uiso 1 1 calc R U . . .
C8 C 0.8445(7) 0.9624(5) 0.5962(6) 0.0631(16) Uani 1 1 d . . . . .
H8 H 0.851938 1.051547 0.652320 0.076 Uiso 1 1 calc R U . . .
C17 C 0.4574(5) -0.1022(5) 0.2154(4) 0.0436(10) Uani 1 1 d . . . . .
H17 H 0.458357 -0.019371 0.276794 0.052 Uiso 1 1 calc R U . . .
C10 C 0.7331(6) 0.7846(5) 0.4066(6) 0.0544(12) Uani 1 1 d . . . . .
H10 H 0.664839 0.754760 0.334429 0.065 Uiso 1 1 calc R U . . .
C9 C 0.7448(7) 0.9168(6) 0.4911(7) 0.0688(17) Uani 1 1 d . . . . .
H9 H 0.683607 0.974857 0.475553 0.083 Uiso 1 1 calc R U . . .
Br1 Br 0.63460(7) -0.34033(6) -0.20829(5) 0.06318(17) Uani 1 1 d . . . . .
O2 O 0.3661(5) -0.2203(5) 0.2163(4) 0.0692(11) Uani 1 1 d . . . . .
C15 C 0.5515(5) -0.1960(4) 0.0176(4) 0.0367(8) Uani 1 1 d . . . . .
H15 H 0.470076 -0.282998 0.006162 0.044 Uiso 1 1 calc R U . . .
C14 C 0.6545(5) -0.1813(5) -0.0683(4) 0.0388(9) Uani 1 1 d . . . . .
C19 C 1.0024(6) 0.6138(6) 0.1817(5) 0.0539(12) Uani 1 1 d . . . . .
H19A H 1.064820 0.680889 0.255634 0.065 Uiso 1 1 calc R U . . .
H19B H 1.054160 0.546782 0.139279 0.065 Uiso 1 1 calc R U . . .
O3 O 0.9446(6) 0.6895(6) 0.0996(6) 0.1018(18) Uani 1 1 d . . . . .
C18 C 0.7934(7) 0.6133(7) 0.1140(5) 0.0623(14) Uani 1 1 d . . . . .
H18A H 0.738436 0.546010 0.036967 0.075 Uiso 1 1 calc R U . . .
H18B H 0.737829 0.680087 0.149678 0.075 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
I1 C2 2.062(4) . ?
O1 C1 1.359(4) . ?
O1 C4 1.442(5) . ?
N1 C1 1.264(5) . ?
N1 C11 1.405(5) . ?
C3 C2 1.331(5) . ?
C3 C5 1.481(5) . ?
C3 C4 1.506(5) . ?
C5 C6 1.380(6) . ?
C5 C10 1.384(6) . ?
C2 C1 1.463(5) . ?
C4 C19 1.530(6) . ?
C4 C18 1.531(6) . ?
C6 C7 1.387(7) . ?
C7 C8 1.368(9) . ?
C16 C15 1.396(5) . ?
C16 C11 1.401(5) . ?
C16 C17 1.473(5) . ?
C11 C12 1.396(5) . ?
C12 C13 1.383(6) . ?
C13 C14 1.391(6) . ?
C8 C9 1.354(9) . ?
C17 O2 1.198(6) . ?
C10 C9 1.384(7) . ?
Br1 C14 1.893(4) . ?
C15 C14 1.365(6) . ?
C19 O3 1.418(7) . ?
O3 C18 1.417(8) . ?

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 O1 C4 109.5(3) . . ?
C1 N1 C11 124.0(3) . . ?
C2 C3 C5 127.3(4) . . ?
C2 C3 C4 107.7(3) . . ?
C5 C3 C4 125.0(3) . . ?
C6 C5 C10 118.7(4) . . ?
C6 C5 C3 120.3(4) . . ?
C10 C5 C3 120.9(4) . . ?
C3 C2 C1 109.8(3) . . ?
C3 C2 I1 129.7(3) . . ?
C1 C2 I1 120.5(3) . . ?
N1 C1 O1 126.7(3) . . ?
N1 C1 C2 125.2(3) . . ?
O1 C1 C2 108.0(3) . . ?
O1 C4 C3 104.8(3) . . ?
O1 C4 C19 113.0(4) . . ?
C3 C4 C19 119.3(4) . . ?
O1 C4 C18 112.5(4) . . ?
C3 C4 C18 122.6(4) . . ?
C19 C4 C18 84.0(4) . . ?
C5 C6 C7 120.2(5) . . ?
C8 C7 C6 120.4(5) . . ?
C15 C16 C11 120.2(4) . . ?
C15 C16 C17 118.5(4) . . ?
C11 C16 C17 121.3(3) . . ?
C12 C11 C16 118.8(3) . . ?
C12 C11 N1 125.0(4) . . ?
C16 C11 N1 116.0(3) . . ?
C13 C12 C11 120.4(4) . . ?
C12 C13 C14 119.8(4) . . ?
C9 C8 C7 119.9(5) . . ?
O2 C17 C16 123.8(4) . . ?
C9 C10 C5 120.3(5) . . ?
C8 C9 C10 120.5(5) . . ?
C14 C15 C16 120.0(4) . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 Br1 119.9(3) . . ?
C13 C14 Br1 119.4(3) . . ?
O3 C19 C4 91.6(4) . . ?
C19 O3 C18 92.6(4) . . ?
O3 C18 C4 91.6(4) . . ?

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
C2 C3 C5 C6 63.5(6) . . . . ?
C4 C3 C5 C6 -115.2(5) . . . . ?
C2 C3 C5 C10 -113.2(5) . . . . ?
C4 C3 C5 C10 68.1(6) . . . . ?
C5 C3 C2 C1 177.6(4) . . . . ?
C4 C3 C2 C1 -3.5(5) . . . . ?
C5 C3 C2 I1 -0.3(6) . . . . ?
C4 C3 C2 I1 178.5(3) . . . . ?
C11 N1 C1 O1 0.4(7) . . . . ?
C11 N1 C1 C2 176.9(4) . . . . ?
C4 O1 C1 N1 177.5(4) . . . . ?
C4 O1 C1 C2 0.5(4) . . . . ?
C3 C2 C1 N1 -175.0(4) . . . . ?
I1 C2 C1 N1 3.1(6) . . . . ?
C3 C2 C1 O1 2.0(5) . . . . ?
I1 C2 C1 O1 -179.8(3) . . . . ?
C1 O1 C4 C3 -2.5(4) . . . . ?
C1 O1 C4 C19 129.0(4) . . . . ?
C1 O1 C4 C18 -138.0(4) . . . . ?
C2 C3 C4 O1 3.7(4) . . . . ?
C5 C3 C4 O1 -177.4(4) . . . . ?
C2 C3 C4 C19 -124.0(4) . . . . ?
C5 C3 C4 C19 54.9(6) . . . . ?
C2 C3 C4 C18 133.4(4) . . . . ?
C5 C3 C4 C18 -47.7(6) . . . . ?
C10 C5 C6 C7 -0.1(7) . . . . ?
C3 C5 C6 C7 -176.9(4) . . . . ?
C5 C6 C7 C8 0.4(7) . . . . ?
C15 C16 C11 C12 -1.7(6) . . . . ?
C17 C16 C11 C12 178.3(4) . . . . ?
C15 C16 C11 N1 -177.5(3) . . . . ?
C17 C16 C11 N1 2.5(5) . . . . ?
C1 N1 C11 C12 36.3(6) . . . . ?
C1 N1 C11 C16 -148.2(4) . . . . ?
C16 C11 C12 C13 0.3(6) . . . . ?
N1 C11 C12 C13 175.7(4) . . . . ?
C11 C12 C13 C14 1.1(7) . . . . ?
C6 C7 C8 C9 -0.2(8) . . . . ?
C15 C16 C17 O2 11.1(7) . . . . ?
C11 C16 C17 O2 -168.9(5) . . . . ?
C6 C5 C10 C9 -0.3(7) . . . . ?
C3 C5 C10 C9 176.4(5) . . . . ?
C7 C8 C9 C10 -0.3(9) . . . . ?
C5 C10 C9 C8 0.5(9) . . . . ?
C11 C16 C15 C14 1.8(6) . . . . ?
C17 C16 C15 C14 -178.2(4) . . . . ?
C16 C15 C14 C13 -0.4(6) . . . . ?
C16 C15 C14 Br1 178.3(3) . . . . ?
C12 C13 C14 C15 -1.1(7) . . . . ?
C12 C13 C14 Br1 -179.7(3) . . . . ?
O1 C4 C19 O3 114.6(4) . . . . ?
C3 C4 C19 O3 -121.6(5) . . . . ?
C18 C4 C19 O3 2.7(4) . . . . ?
C4 C19 O3 C18 -2.9(5) . . . . ?
C19 O3 C18 C4 2.9(5) . . . . ?
O1 C4 C18 O3 -115.1(5) . . . . ?
C3 C4 C18 O3 118.5(5) . . . . ?
C19 C4 C18 O3 -2.7(4) . . . . ?

_refine_diff_density_max         2.642
_refine_diff_density_min         -1.580
_refine_diff_density_rms         0.110

