# Supplementary Information (SI) for Dalton Transactions.
# 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
_audit_block_doi                 10.5517/ccdc.csd.cc2qr04n
_database_code_depnum_ccdc_archive 'CCDC 2524551'
loop_
_audit_author_name
_audit_author_address
'Mengfan Duan'
;Institute of Material Structure, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2026-01-21 deposited with the CCDC.	2026-03-16 downloaded from the CCDC.
;
_audit_creation_date             2026-01-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H5 Br I N3 O'
_chemical_formula_sum            'C5 H5 Br I N3 O'
_chemical_formula_weight         329.93
_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'
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0035(3)
_cell_length_b                   7.5923(5)
_cell_length_c                   11.9383(9)
_cell_angle_alpha                78.114(6)
_cell_angle_beta                 82.770(6)
_cell_angle_gamma                81.684(6)
_cell_volume                     436.96(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1660
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      28.3730
_cell_measurement_theta_min      2.9370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.185
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             304
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0938
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3870
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.438
_diffrn_reflns_theta_min         2.762
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1579
_reflns_number_total             2058
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         1.125
_refine_diff_density_min         -0.892
_refine_diff_density_rms         0.206
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         2058
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      0.911
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0680
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C2(H2)
2.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
I1 I 0.21763(8) 0.74527(5) 0.50622(3) 0.02111(12) Uani 1 1 d . . . . .
Br1 Br -0.00568(12) 0.83978(8) 0.31463(4) 0.02482(16) Uani 1 1 d . . . . .
O1 O 0.3181(8) 0.1922(5) 0.9217(3) 0.0244(10) Uani 1 1 d . . . . .
N2 N 0.4332(9) 0.6607(6) 0.6835(3) 0.0155(10) Uani 1 1 d . . . . .
N3 N 0.7314(9) 0.1879(6) 0.9815(3) 0.0221(11) Uani 1 1 d . . . . .
H3A H 0.724487 0.080879 1.026598 0.027 Uiso 1 1 calc R U . . .
H3B H 0.874480 0.245068 0.976878 0.027 Uiso 1 1 calc R U . . .
N1 N 0.7297(9) 0.5468(6) 0.8712(4) 0.0225(11) Uani 1 1 d . . . . .
C1 C 0.5926(11) 0.7680(8) 0.7105(4) 0.0224(13) Uani 1 1 d . . . . .
H1 H 0.604767 0.885593 0.665070 0.027 Uiso 1 1 calc R U . . .
C3 C 0.5562(11) 0.4465(8) 0.8454(4) 0.0188(12) Uani 1 1 d . . . . .
C5 C 0.5268(11) 0.2627(7) 0.9206(4) 0.0165(12) Uani 1 1 d . . . . .
C4 C 0.4048(11) 0.5005(7) 0.7523(4) 0.0226(13) Uani 1 1 d . . . . .
H4 H 0.282696 0.424992 0.737577 0.027 Uiso 1 1 calc R U . . .
C2 C 0.7416(11) 0.7092(8) 0.8046(5) 0.0235(13) Uani 1 1 d . . . . .
H2 H 0.855763 0.787679 0.821900 0.028 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 Br1 2.5943(6) . ?
I1 N2 2.423(4) . ?
O1 C5 1.238(6) . ?
N2 C1 1.328(7) . ?
N2 C4 1.336(6) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C5 1.322(6) . ?
N1 C3 1.336(7) . ?
N1 C2 1.328(7) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(7) . ?
C3 C5 1.512(7) . ?
C3 C4 1.382(7) . ?
C4 H4 0.9500 . ?
C2 H2 0.9500 . ?

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
N2 I1 Br1 178.86(11) . . ?
C1 N2 I1 120.7(3) . . ?
C1 N2 C4 119.1(5) . . ?
C4 N2 I1 120.1(4) . . ?
H3A N3 H3B 120.0 . . ?
C5 N3 H3A 120.0 . . ?
C5 N3 H3B 120.0 . . ?
C2 N1 C3 115.9(5) . . ?
N2 C1 H1 119.8 . . ?
N2 C1 C2 120.3(5) . . ?
C2 C1 H1 119.8 . . ?
N1 C3 C5 118.4(4) . . ?
N1 C3 C4 123.5(5) . . ?
C4 C3 C5 118.1(5) . . ?
O1 C5 N3 124.4(5) . . ?
O1 C5 C3 119.2(4) . . ?
N3 C5 C3 116.4(5) . . ?
N2 C4 C3 118.8(5) . . ?
N2 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C2 C1 122.1(5) . . ?
N1 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?

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
I1 N2 C1 C2 -172.1(4) . . . . ?
I1 N2 C4 C3 172.2(4) . . . . ?
N2 C1 C2 N1 -0.6(9) . . . . ?
N1 C3 C5 O1 158.3(5) . . . . ?
N1 C3 C5 N3 -21.8(7) . . . . ?
N1 C3 C4 N2 0.5(8) . . . . ?
C1 N2 C4 C3 -4.2(8) . . . . ?
C3 N1 C2 C1 -3.0(8) . . . . ?
C5 C3 C4 N2 -178.5(5) . . . . ?
C4 N2 C1 C2 4.3(8) . . . . ?
C4 C3 C5 O1 -22.7(8) . . . . ?
C4 C3 C5 N3 157.2(5) . . . . ?
C2 N1 C3 C5 -178.0(5) . . . . ?
C2 N1 C3 C4 3.0(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
