# Supplementary Information (SI) for ChemComm.
# 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_A1CMI
_database_code_depnum_ccdc_archive 'CCDC 2355474'
loop_
_audit_author_name
_audit_author_address
'Connor P. McLoughlin'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 F6 I O3 S2'
_chemical_formula_sum            'C10 H9 F6 I O3 S2'
_chemical_formula_weight         482.19

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
I I -0.4742 1.8119 '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                   11.4528(12)
_cell_length_b                   9.0531(9)
_cell_length_c                   14.0965(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.756(2)
_cell_angle_gamma                90
_cell_volume                     1459.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9796
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.47

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.194
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.031
_exptl_absorpt_coefficient_mu    2.554
_shelx_estimated_absorpt_T_min   0.578
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   'Empirical, SADABS (multi-scan)'
_exptl_absorpt_correction_T_min  0.7069
_exptl_absorpt_correction_T_max  0.7899
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon2 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12715
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.675
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_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             3344
_reflns_number_gt                3175
_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       'Apex3 (2019.1) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0211P)²+5.2773P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3344
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0645
_refine_ls_wR_factor_gt          0.0634
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
I1 I 0.33694(2) 0.45356(2) 0.34490(2) 0.01965(7) Uani 1 1 d . . . . .
S1 S 0.40149(6) 0.79977(7) 0.34807(5) 0.01256(13) Uani 1 1 d . . . . .
S2 S 0.04349(6) 0.75275(10) 0.63113(5) 0.02095(16) Uani 1 1 d . . . . .
F1 F 0.90180(15) 0.6783(2) 0.37746(13) 0.0246(4) Uani 1 1 d . . . . .
F2 F -0.07437(17) 0.8190(3) 0.66642(15) 0.0374(5) Uani 1 1 d . . . . .
F3 F 0.02648(16) 0.8540(2) 0.53987(14) 0.0251(4) Uani 1 1 d . . . . .
F4 F 0.10953(18) 0.8816(3) 0.68518(16) 0.0383(5) Uani 1 1 d . . . . .
F5 F 0.05279(18) 0.6547(3) 0.72249(13) 0.0356(5) Uani 1 1 d . . . . .
F6 F -0.03181(16) 0.6295(2) 0.57925(14) 0.0277(4) Uani 1 1 d . . . . .
O1 O 0.36531(18) 0.7899(2) 0.24957(14) 0.0170(4) Uani 1 1 d . . . . .
O2 O 0.38344(19) 0.9377(2) 0.39747(15) 0.0184(4) Uani 1 1 d . . . . .
O3 O 0.16155(18) 0.6807(2) 0.59838(14) 0.0181(4) Uani 1 1 d . . . . .
C1 C 0.7859(2) 0.7031(3) 0.3724(2) 0.0177(6) Uani 1 1 d . . . . .
C2 C 0.7398(3) 0.7976(3) 0.4384(2) 0.0188(6) Uani 1 1 d . . . . .
H2 H 0.788615 0.842935 0.486350 0.023 Uiso 1 1 calc R U . . .
C3 C 0.6201(3) 0.8239(3) 0.4323(2) 0.0167(6) Uani 1 1 d . . . . .
H3 H 0.585676 0.887923 0.476498 0.020 Uiso 1 1 calc R U . . .
C4 C 0.5512(2) 0.7558(3) 0.36105(19) 0.0133(5) Uani 1 1 d . . . . .
C5 C 0.5997(2) 0.6604(3) 0.29531(19) 0.0136(5) Uani 1 1 d . . . . .
H5 H 0.551466 0.614899 0.246981 0.016 Uiso 1 1 calc R U . . .
C6 C 0.7191(2) 0.6332(3) 0.3017(2) 0.0160(5) Uani 1 1 d . . . . .
H6 H 0.753963 0.568013 0.258491 0.019 Uiso 1 1 calc R U . . .
C7 C 0.3227(2) 0.6635(3) 0.4122(2) 0.0135(5) Uani 1 1 d . . . . .
C8 C 0.3473(2) 0.6684(3) 0.5226(2) 0.0155(5) Uani 1 1 d . . . . .
H8A H 0.347716 0.570057 0.553335 0.019 Uiso 1 1 calc R U . . .
H8B H 0.417542 0.726086 0.542853 0.019 Uiso 1 1 calc R U . . .
C9 C 0.2319(2) 0.7533(3) 0.5299(2) 0.0158(5) Uani 1 1 d . . . . .
H9 H 0.243298 0.861061 0.542793 0.019 Uiso 1 1 calc R U . . .
C10 C 0.1958(2) 0.7194(3) 0.4256(2) 0.0161(5) Uani 1 1 d . . . . .
H10A H 0.174420 0.808071 0.387487 0.019 Uiso 1 1 calc R U . . .
H10B H 0.135390 0.641672 0.417539 0.019 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 C7 2.134(3) . ?
S1 O1 1.433(2) . ?
S1 O2 1.450(2) . ?
S1 C4 1.761(3) . ?
S1 C7 1.798(3) . ?
S2 F5 1.563(2) . ?
S2 F4 1.568(2) . ?
S2 F6 1.570(2) . ?
S2 F2 1.579(2) . ?
S2 F3 1.584(2) . ?
S2 O3 1.589(2) . ?
F1 C1 1.345(3) . ?
O3 C9 1.444(3) . ?
C1 C6 1.380(4) . ?
C1 C2 1.386(4) . ?
C2 C3 1.390(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(4) . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C10 1.559(4) . ?
C7 C8 1.568(4) . ?
C8 C9 1.537(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.538(4) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
O1 S1 O2 118.57(13) . . ?
O1 S1 C4 108.75(13) . . ?
O2 S1 C4 107.77(13) . . ?
O1 S1 C7 108.41(13) . . ?
O2 S1 C7 105.25(13) . . ?
C4 S1 C7 107.60(13) . . ?
F5 S2 F4 90.56(14) . . ?
F5 S2 F6 89.68(13) . . ?
F4 S2 F6 175.52(12) . . ?
F5 S2 F2 88.94(12) . . ?
F4 S2 F2 87.93(12) . . ?
F6 S2 F2 87.60(12) . . ?
F5 S2 F3 176.69(11) . . ?
F4 S2 F3 90.09(13) . . ?
F6 S2 F3 89.42(11) . . ?
F2 S2 F3 87.84(12) . . ?
F5 S2 O3 88.93(11) . . ?
F4 S2 O3 92.82(12) . . ?
F6 S2 O3 91.66(12) . . ?
F2 S2 O3 177.75(13) . . ?
F3 S2 O3 94.29(11) . . ?
C9 O3 S2 121.12(19) . . ?
F1 C1 C6 118.3(3) . . ?
F1 C1 C2 118.3(3) . . ?
C6 C1 C2 123.4(3) . . ?
C1 C2 C3 118.1(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 S1 119.4(2) . . ?
C5 C4 S1 119.0(2) . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C10 C7 C8 89.7(2) . . ?
C10 C7 S1 109.34(19) . . ?
C8 C7 S1 114.1(2) . . ?
C10 C7 I1 115.78(19) . . ?
C8 C7 I1 116.90(19) . . ?
S1 C7 I1 109.66(13) . . ?
C9 C8 C7 88.1(2) . . ?
C9 C8 H8A 114.0 . . ?
C7 C8 H8A 114.0 . . ?
C9 C8 H8B 114.0 . . ?
C7 C8 H8B 114.0 . . ?
H8A C8 H8B 111.2 . . ?
O3 C9 C8 109.1(2) . . ?
O3 C9 C10 114.5(2) . . ?
C8 C9 C10 91.6(2) . . ?
O3 C9 H9 113.2 . . ?
C8 C9 H9 113.2 . . ?
C10 C9 H9 113.2 . . ?
C9 C10 C7 88.4(2) . . ?
C9 C10 H10A 113.9 . . ?
C7 C10 H10A 113.9 . . ?
C9 C10 H10B 113.9 . . ?
C7 C10 H10B 113.9 . . ?
H10A C10 H10B 111.1 . . ?

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
F5 S2 O3 C9 -159.2(2) . . . . ?
F4 S2 O3 C9 -68.7(2) . . . . ?
F6 S2 O3 C9 111.1(2) . . . . ?
F3 S2 O3 C9 21.6(2) . . . . ?
F1 C1 C2 C3 179.4(3) . . . . ?
C6 C1 C2 C3 -0.6(5) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C2 C3 C4 S1 -175.4(2) . . . . ?
O1 S1 C4 C3 147.7(2) . . . . ?
O2 S1 C4 C3 18.0(3) . . . . ?
C7 S1 C4 C3 -95.1(2) . . . . ?
O1 S1 C4 C5 -28.1(3) . . . . ?
O2 S1 C4 C5 -157.8(2) . . . . ?
C7 S1 C4 C5 89.1(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
S1 C4 C5 C6 175.8(2) . . . . ?
F1 C1 C6 C5 -179.0(3) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
O1 S1 C7 C10 -77.4(2) . . . . ?
O2 S1 C7 C10 50.4(2) . . . . ?
C4 S1 C7 C10 165.12(19) . . . . ?
O1 S1 C7 C8 -176.14(19) . . . . ?
O2 S1 C7 C8 -48.3(2) . . . . ?
C4 S1 C7 C8 66.4(2) . . . . ?
O1 S1 C7 I1 50.50(16) . . . . ?
O2 S1 C7 I1 178.32(13) . . . . ?
C4 S1 C7 I1 -66.95(16) . . . . ?
C10 C7 C8 C9 -11.1(2) . . . . ?
S1 C7 C8 C9 100.0(2) . . . . ?
I1 C7 C8 C9 -130.15(19) . . . . ?
S2 O3 C9 C8 172.58(19) . . . . ?
S2 O3 C9 C10 -86.4(3) . . . . ?
C7 C8 C9 O3 128.0(2) . . . . ?
C7 C8 C9 C10 11.3(2) . . . . ?
O3 C9 C10 C7 -123.2(2) . . . . ?
C8 C9 C10 C7 -11.4(2) . . . . ?
C8 C7 C10 C9 11.1(2) . . . . ?
S1 C7 C10 C9 -104.5(2) . . . . ?
I1 C7 C10 C9 131.1(2) . . . . ?

_refine_diff_density_max         1.195
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.107



