# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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 2400925'
loop_
_audit_author_name
_audit_author_address
'Fang Wei'
; Jiangxi Science and  Technology Normal University
China
;
_audit_update_record             
;
2024-11-06 deposited with the CCDC.	2025-04-29 downloaded from the CCDC.
;
_audit_creation_date             2024-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 I O2 S'
_chemical_formula_sum            'C16 H15 I O2 S'
_chemical_formula_weight         398.24
_chemical_absolute_configuration ?
_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'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.5284(3)
_cell_length_b                   9.1429(4)
_cell_length_c                   31.8213(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1608.43(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    655(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.677
_shelx_estimated_absorpt_T_min   0.641
_exptl_absorpt_coefficient_mu    2.119
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1586 before and 0.0816 after correction.
The Ratio of minimum to maximum transmission is 0.5453.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            12643
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.275
_diffrn_reflns_theta_min         2.560
_diffrn_ambient_temperature      655.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3501
_reflns_number_total             3922
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.919
_refine_diff_density_min         -0.989
_refine_diff_density_rms         0.125
_refine_ls_abs_structure_details 
;
 Flack x determined using 1261 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.068(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0471P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1083
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00E(H00F), C00F(H00G),
 C00G(H00H), C00I(H00I), C00J(H00J)
2.b Idealised Me refined as rotating group:
 C00D(H00C,H00D,H00E), C00K(H00K,H00L,H00M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
I001 I 0.09830(8) 0.32132(4) 0.45859(2) 0.05888(17) Uani 1 1 d . . . . .
S002 S 0.6116(3) 0.44576(16) 0.34578(4) 0.0489(3) Uani 1 1 d . . . . .
O003 O 0.8152(8) 0.3505(7) 0.34146(15) 0.0722(14) Uani 1 1 d . . . . .
O004 O 0.6558(10) 0.5957(5) 0.35593(13) 0.0669(13) Uani 1 1 d . . . . .
C005 C 0.3209(10) 0.4352(6) 0.41479(16) 0.0414(11) Uani 1 1 d . . . . .
C006 C 0.3434(9) 0.5930(6) 0.42614(16) 0.0403(11) Uani 1 1 d . . . . .
C007 C 0.4131(11) 0.3620(6) 0.38313(16) 0.0451(11) Uani 1 1 d . . . . .
C008 C 0.5357(10) 0.6397(7) 0.45067(17) 0.0493(13) Uani 1 1 d . . . . .
H008 H 0.651628 0.573030 0.459687 0.059 Uiso 1 1 calc R . . . .
C009 C 0.1675(10) 0.6913(6) 0.41359(18) 0.0502(13) Uani 1 1 d . . . . .
H009 H 0.036574 0.659376 0.397696 0.060 Uiso 1 1 calc R . . . .
C00A C 0.1866(12) 0.8378(6) 0.4248(2) 0.0581(14) Uani 1 1 d . . . . .
H00A H 0.068717 0.904237 0.416405 0.070 Uiso 1 1 calc R . . . .
C00B C 0.2396(11) 0.5283(6) 0.29444(19) 0.0512(13) Uani 1 1 d . . . . .
H00B H 0.186079 0.585508 0.316754 0.061 Uiso 1 1 calc R . . . .
C00C C 0.4432(10) 0.4409(6) 0.29832(16) 0.0434(11) Uani 1 1 d . . . . .
C00D C 0.3752(16) 0.2024(6) 0.3732(2) 0.0672(18) Uani 1 1 d . . . . .
H00C H 0.389918 0.187496 0.343403 0.101 Uiso 1 1 calc GR . . . .
H00D H 0.216799 0.173169 0.382204 0.101 Uiso 1 1 calc GR . . . .
H00E H 0.494840 0.145004 0.387513 0.101 Uiso 1 1 calc GR . . . .
C00E C 0.5551(13) 0.7868(7) 0.4618(2) 0.0596(15) Uani 1 1 d . . . . .
H00F H 0.684279 0.818446 0.478174 0.071 Uiso 1 1 calc R . . . .
C00F C 0.1190(12) 0.5281(7) 0.2567(2) 0.0587(15) Uani 1 1 d . . . . .
H00G H -0.015866 0.587878 0.253547 0.070 Uiso 1 1 calc R . . . .
C00G C 0.5173(13) 0.3531(8) 0.2663(2) 0.0607(16) Uani 1 1 d . . . . .
H00H H 0.651458 0.292905 0.269700 0.073 Uiso 1 1 calc R . . . .
C00H C 0.1906(13) 0.4424(8) 0.2233(2) 0.0606(16) Uani 1 1 d . . . . .
C00I C 0.3832(15) 0.8844(6) 0.44854(19) 0.0590(15) Uani 1 1 d . . . . .
H00I H 0.398146 0.982786 0.455496 0.071 Uiso 1 1 calc R . . . .
C00J C 0.3931(16) 0.3537(8) 0.2287(2) 0.0681(17) Uani 1 1 d . . . . .
H00J H 0.444970 0.294340 0.206738 0.082 Uiso 1 1 calc R . . . .
C00K C 0.0581(19) 0.4438(10) 0.1823(2) 0.090(3) Uani 1 1 d . . . . .
H00K H -0.112959 0.445118 0.187431 0.134 Uiso 1 1 calc GR . . . .
H00L H 0.099335 0.357868 0.166496 0.134 Uiso 1 1 calc GR . . . .
H00M H 0.103044 0.529316 0.166610 0.134 Uiso 1 1 calc GR . . . .


_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
I001 C005 2.131(5) . ?
S002 O003 1.430(5) . ?
S002 O004 1.430(5) . ?
S002 C007 1.789(6) . ?
S002 C00C 1.775(5) . ?
C005 C006 1.493(7) . ?
C005 C007 1.312(7) . ?
C006 C008 1.386(7) . ?
C006 C009 1.383(7) . ?
C007 C00D 1.508(7) . ?
C008 H008 0.9300 . ?
C008 C00E 1.394(9) . ?
C009 H009 0.9300 . ?
C009 C00A 1.390(8) . ?
C00A H00A 0.9300 . ?
C00A C00I 1.391(9) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.386(8) . ?
C00B C00F 1.374(8) . ?
C00C C00G 1.361(8) . ?
C00D H00C 0.9600 . ?
C00D H00D 0.9600 . ?
C00D H00E 0.9600 . ?
C00E H00F 0.9300 . ?
C00E C00I 1.371(10) . ?
C00F H00G 0.9300 . ?
C00F C00H 1.378(10) . ?
C00G H00H 0.9300 . ?
C00G C00J 1.379(9) . ?
C00H C00J 1.393(10) . ?
C00H C00K 1.497(9) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9600 . ?
C00K H00L 0.9600 . ?
C00K H00M 0.9600 . ?

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
O003 S002 C007 106.6(3) . . ?
O003 S002 C00C 108.4(3) . . ?
O004 S002 O003 118.1(3) . . ?
O004 S002 C007 111.4(3) . . ?
O004 S002 C00C 107.8(3) . . ?
C00C S002 C007 103.5(3) . . ?
C006 C005 I001 111.2(3) . . ?
C007 C005 I001 118.5(4) . . ?
C007 C005 C006 130.2(5) . . ?
C008 C006 C005 119.8(5) . . ?
C009 C006 C005 120.0(5) . . ?
C009 C006 C008 120.1(5) . . ?
C005 C007 S002 122.0(4) . . ?
C005 C007 C00D 126.9(6) . . ?
C00D C007 S002 111.1(4) . . ?
C006 C008 H008 120.0 . . ?
C006 C008 C00E 119.9(5) . . ?
C00E C008 H008 120.0 . . ?
C006 C009 H009 120.0 . . ?
C006 C009 C00A 119.9(5) . . ?
C00A C009 H009 120.0 . . ?
C009 C00A H00A 120.2 . . ?
C009 C00A C00I 119.6(5) . . ?
C00I C00A H00A 120.2 . . ?
C00C C00B H00B 121.0 . . ?
C00F C00B H00B 121.0 . . ?
C00F C00B C00C 118.1(6) . . ?
C00B C00C S002 119.2(4) . . ?
C00G C00C S002 119.6(5) . . ?
C00G C00C C00B 121.2(6) . . ?
C007 C00D H00C 109.5 . . ?
C007 C00D H00D 109.5 . . ?
C007 C00D H00E 109.5 . . ?
H00C C00D H00D 109.5 . . ?
H00C C00D H00E 109.5 . . ?
H00D C00D H00E 109.5 . . ?
C008 C00E H00F 120.1 . . ?
C00I C00E C008 119.7(6) . . ?
C00I C00E H00F 120.1 . . ?
C00B C00F H00G 118.8 . . ?
C00B C00F C00H 122.4(6) . . ?
C00H C00F H00G 118.8 . . ?
C00C C00G H00H 120.1 . . ?
C00C C00G C00J 119.8(6) . . ?
C00J C00G H00H 120.1 . . ?
C00F C00H C00J 117.8(6) . . ?
C00F C00H C00K 121.8(7) . . ?
C00J C00H C00K 120.4(7) . . ?
C00A C00I H00I 119.7 . . ?
C00E C00I C00A 120.6(5) . . ?
C00E C00I H00I 119.7 . . ?
C00G C00J C00H 120.6(6) . . ?
C00G C00J H00J 119.7 . . ?
C00H C00J H00J 119.7 . . ?
C00H C00K H00K 109.5 . . ?
C00H C00K H00L 109.5 . . ?
C00H C00K H00M 109.5 . . ?
H00K C00K H00L 109.5 . . ?
H00K C00K H00M 109.5 . . ?
H00L C00K H00M 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
