# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_07152016-1
_database_code_depnum_ccdc_archive 'CCDC 2488414'
loop_
_audit_author_name
_audit_author_address
'Akio Saito'
;Tokyo University of Agriculture and Technology
Japan
;
_audit_update_record             
;
2025-09-16 deposited with the CCDC.	2025-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'3-methylbenzo[b]iodol-1-ium trifluoromethanesulfonate'
_chemical_name_common            ?
_chemical_melting_point          441-442
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 F3 I O3 S'
_chemical_formula_weight         392.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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                   7.4211(2)
_cell_length_b                   15.2675(3)
_cell_length_c                   11.4190(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.269(7)
_cell_angle_gamma                90
_cell_volume                     1291.69(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6624
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      66.6

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.016
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    21.361
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.349
_exptl_absorpt_process_details   
;
FS_Process, CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 RX
_diffrn_measurement_device       
;
Crystal Goniometer
;
_diffrn_measurement_device_type  
;
Rigaku RAXIS conversion
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            8117
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.841
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_full        66.590
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2249
_reflns_number_gt                1807
_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       
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_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)+(0.0384P)²] 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         2249
_refine_ls_number_parameters     195
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.64418(4) 0.09281(2) 0.35952(3) 0.03581(17) Uani 1 1 d . . . . .
C12 C 0.6683(7) -0.0219(4) 0.2653(5) 0.0398(14) Uani 1 1 d . . . . .
H12 H 0.6388 -0.0266 0.1834 0.048 Uiso 1 1 calc R U . . .
C21 C 0.7597(8) -0.1779(4) 0.2801(6) 0.0575(19) Uani 1 1 d . . . . .
H21A H 0.8873 -0.1938 0.2926 0.086 Uiso 1 1 calc R U . . .
H21B H 0.7264 -0.1771 0.1958 0.086 Uiso 1 1 calc R U . . .
H21C H 0.6852 -0.2210 0.3187 0.086 Uiso 1 1 calc R U . . .
C1 C 0.7423(6) 0.0125(3) 0.4978(4) 0.0302(12) Uani 1 1 d . . . . .
C2 C 0.7752(7) 0.0387(4) 0.6124(5) 0.0376(14) Uani 1 1 d . . . . .
H2 H 0.7536 0.0972 0.6365 0.045 Uiso 1 1 calc R U . . .
C3 C 0.8417(7) -0.0246(4) 0.6914(5) 0.0423(15) Uani 1 1 d . . . . .
H3 H 0.8666 -0.0095 0.7714 0.051 Uiso 1 1 calc R U . . .
C4 C 0.8719(8) -0.1100(5) 0.6537(6) 0.050(2) Uani 1 1 d . . . . .
H4 H 0.9184 -0.1525 0.7082 0.060 Uiso 1 1 calc R U . . .
C5 C 0.8351(8) -0.1332(4) 0.5391(6) 0.0436(15) Uani 1 1 d . . . . .
H5 H 0.8541 -0.1919 0.5151 0.052 Uiso 1 1 calc R U . . .
C6 C 0.7697(8) -0.0714(4) 0.4568(5) 0.0353(14) Uani 1 1 d . . . . .
C7 C 0.7292(9) -0.0883(4) 0.3312(6) 0.0444(17) Uani 1 1 d . . . . .
S1 S 0.6750(3) 0.29546(14) 0.57996(19) 0.0408(5) Uani 0.752(3) 1 d D . P A 1
O3 O 0.5862(8) 0.2251(3) 0.5141(5) 0.0492(15) Uani 0.752(3) 1 d D . P A 1
O4 O 0.8243(7) 0.2685(4) 0.6551(4) 0.0530(17) Uani 0.752(3) 1 d D . P A 1
O5 O 0.5562(11) 0.3553(7) 0.6338(6) 0.0391(18) Uani 0.752(3) 1 d D . P A 1
C8 C 0.7751(14) 0.3611(6) 0.4672(8) 0.052(2) Uani 0.752(3) 1 d D . P A 1
F1 F 0.8632(9) 0.4306(4) 0.5174(6) 0.084(2) Uani 0.752(3) 1 d D . P A 1
F2 F 0.6543(8) 0.3905(4) 0.3896(5) 0.087(2) Uani 0.752(3) 1 d D . P A 1
F3 F 0.8962(15) 0.3143(4) 0.4134(8) 0.067(2) Uani 0.752(3) 1 d D . P A 1
S1A S 0.6070(10) 0.3079(5) 0.5286(6) 0.0408(5) Uani 0.248(3) 1 d D . P A 2
O3A O 0.685(2) 0.2259(10) 0.5625(15) 0.0492(15) Uani 0.248(3) 1 d D . P A 2
O4A O 0.516(4) 0.362(2) 0.610(2) 0.0391(18) Uani 0.248(3) 1 d D . P A 2
O5A O 0.500(2) 0.3089(11) 0.4204(10) 0.058(5) Uani 0.248(3) 1 d D . P A 2
C8A C 0.806(3) 0.3721(15) 0.495(2) 0.052(2) Uani 0.248(3) 1 d D . P A 2
F1A F 0.751(3) 0.4545(11) 0.4662(19) 0.084(2) Uani 0.248(3) 1 d D . P A 2
F2A F 0.888(5) 0.3466(18) 0.403(3) 0.067(2) Uani 0.248(3) 1 d D . P A 2
F3A F 0.918(2) 0.3769(12) 0.5899(16) 0.084(2) Uani 0.248(3) 1 d D . P A 2


_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 C12 2.069(5) . ?
I1 C1 2.097(5) . ?
C12 C7 1.327(7) . ?
C12 H12 0.9500 . ?
C21 C7 1.510(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C1 C2 1.377(7) . ?
C1 C6 1.382(7) . ?
C2 C3 1.392(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.472(8) . ?
S1 O4 1.423(5) . ?
S1 O5 1.432(6) . ?
S1 O3 1.448(5) . ?
S1 C8 1.823(9) . ?
C8 F2 1.303(10) . ?
C8 F3 1.326(10) . ?
C8 F1 1.356(9) . ?
S1A O3A 1.423(13) . ?
S1A O5A 1.431(12) . ?
S1A O4A 1.441(17) . ?
S1A C8A 1.832(16) . ?
C8A F2A 1.30(2) . ?
C8A F3A 1.332(19) . ?
C8A F1A 1.356(18) . ?

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
C12 I1 C1 82.0(2) . . ?
C7 C12 I1 112.8(4) . . ?
C7 C12 H12 123.6 . . ?
I1 C12 H12 123.6 . . ?
C7 C21 H21A 109.5 . . ?
C7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 C1 C6 124.7(5) . . ?
C2 C1 I1 125.5(4) . . ?
C6 C1 I1 109.8(4) . . ?
C1 C2 C3 116.8(5) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C2 C3 C4 120.4(6) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.6(6) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.7(6) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 116.7(5) . . ?
C1 C6 C7 117.8(5) . . ?
C5 C6 C7 125.4(6) . . ?
C12 C7 C6 117.6(5) . . ?
C12 C7 C21 121.8(6) . . ?
C6 C7 C21 120.6(5) . . ?
O4 S1 O5 113.8(4) . . ?
O4 S1 O3 114.5(4) . . ?
O5 S1 O3 115.0(5) . . ?
O4 S1 C8 104.5(4) . . ?
O5 S1 C8 103.7(6) . . ?
O3 S1 C8 103.5(4) . . ?
F2 C8 F3 109.2(9) . . ?
F2 C8 F1 108.3(8) . . ?
F3 C8 F1 107.1(9) . . ?
F2 C8 S1 112.2(7) . . ?
F3 C8 S1 110.2(7) . . ?
F1 C8 S1 109.8(7) . . ?
O3A S1A O5A 116.1(10) . . ?
O3A S1A O4A 121.6(16) . . ?
O5A S1A O4A 107.2(12) . . ?
O3A S1A C8A 102.0(11) . . ?
O5A S1A C8A 103.1(10) . . ?
O4A S1A C8A 104.1(17) . . ?
F2A C8A F3A 112(2) . . ?
F2A C8A F1A 103.3(19) . . ?
F3A C8A F1A 108(2) . . ?
F2A C8A S1A 115(2) . . ?
F3A C8A S1A 109.4(14) . . ?
F1A C8A S1A 108.1(15) . . ?

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
C6 C1 C2 C3 0.3(8) . . . . ?
I1 C1 C2 C3 -179.6(4) . . . . ?
C1 C2 C3 C4 -0.1(8) . . . . ?
C2 C3 C4 C5 -0.6(9) . . . . ?
C3 C4 C5 C6 1.2(9) . . . . ?
C2 C1 C6 C5 0.2(8) . . . . ?
I1 C1 C6 C5 -179.9(4) . . . . ?
C2 C1 C6 C7 -179.5(5) . . . . ?
I1 C1 C6 C7 0.5(6) . . . . ?
C4 C5 C6 C1 -1.0(9) . . . . ?
C4 C5 C6 C7 178.6(6) . . . . ?
I1 C12 C7 C6 -0.1(7) . . . . ?
I1 C12 C7 C21 -179.1(4) . . . . ?
C1 C6 C7 C12 -0.2(9) . . . . ?
C5 C6 C7 C12 -179.9(6) . . . . ?
C1 C6 C7 C21 178.7(5) . . . . ?
C5 C6 C7 C21 -0.9(9) . . . . ?
O4 S1 C8 F2 179.3(7) . . . . ?
O5 S1 C8 F2 -61.2(8) . . . . ?
O3 S1 C8 F2 59.2(8) . . . . ?
O4 S1 C8 F3 57.5(9) . . . . ?
O5 S1 C8 F3 177.0(8) . . . . ?
O3 S1 C8 F3 -62.6(9) . . . . ?
O4 S1 C8 F1 -60.2(8) . . . . ?
O5 S1 C8 F1 59.3(9) . . . . ?
O3 S1 C8 F1 179.7(7) . . . . ?
O3A S1A C8A F2A 68(2) . . . . ?
O5A S1A C8A F2A -53(2) . . . . ?
O4A S1A C8A F2A -165(2) . . . . ?
O3A S1A C8A F3A -60(2) . . . . ?
O5A S1A C8A F3A 179.6(17) . . . . ?
O4A S1A C8A F3A 68(2) . . . . ?
O3A S1A C8A F1A -177.1(17) . . . . ?
O5A S1A C8A F1A 62(2) . . . . ?
O4A S1A C8A F1A -50(2) . . . . ?

_refine_diff_density_max         0.870
_refine_diff_density_min         -0.938
_refine_diff_density_rms         0.130



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
