# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_22_a
_database_code_depnum_ccdc_archive 'CCDC 2094038'
_audit_update_record             
;
2021-07-02 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 I O4 S'
_chemical_formula_weight         364.14

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.705(4)
_cell_length_b                   15.007(5)
_cell_length_c                   7.459(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.239(3)
_cell_angle_gamma                90.00
_cell_volume                     1264.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6741
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.41

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.913
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    2.697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3766
_exptl_absorpt_correction_T_max  0.5189
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13893
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0127
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         27.41
_reflns_number_total             2837
_reflns_number_gt                2452
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0436P)²+1.0937P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2837
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.444964(19) 0.632663(15) 0.86953(3) 0.05318(10) Uani 1 1 d . . .
S1 S 0.63641(9) 0.62898(7) 0.39418(13) 0.0599(2) Uani 1 1 d . . .
O2 O 0.27149(19) 0.64112(15) 0.4714(3) 0.0499(5) Uani 1 1 d . . .
O4 O -0.1136(2) 0.51230(19) 0.2142(3) 0.0646(7) Uani 1 1 d . . .
O3 O -0.1532(2) 0.60114(18) -0.0466(3) 0.0631(6) Uani 1 1 d . . .
O1 O 0.3870(2) 0.5968(2) 0.2905(3) 0.0669(7) Uani 1 1 d . . .
C2 C 0.4758(3) 0.62848(18) 0.6053(4) 0.0429(6) Uani 1 1 d . . .
C5 C 0.1675(3) 0.6329(2) 0.3262(4) 0.0435(6) Uani 1 1 d . . .
C9 C -0.0183(3) 0.5662(2) 0.2195(4) 0.0446(6) Uani 1 1 d . . .
C10 C 0.0858(3) 0.5712(2) 0.3547(4) 0.0470(7) Uani 1 1 d . . .
H10 H 0.1010 0.5353 0.4600 0.056 Uiso 1 1 calc R . .
C3 C 0.3765(3) 0.6194(2) 0.4384(4) 0.0451(7) Uani 1 1 d . . .
C8 C -0.0415(3) 0.6193(2) 0.0637(4) 0.0467(7) Uani 1 1 d . . .
C1 C 0.5876(3) 0.6336(2) 0.5938(4) 0.0476(7) Uani 1 1 d . . .
H1 H 0.6455 0.6404 0.7052 0.057 Uiso 1 1 calc R . .
C6 C 0.1466(3) 0.6873(2) 0.1735(5) 0.0543(8) Uani 1 1 d . . .
H6 H 0.2034 0.7284 0.1606 0.065 Uiso 1 1 calc R . .
C7 C 0.0386(3) 0.6806(2) 0.0366(5) 0.0572(8) Uani 1 1 d . . .
H7 H 0.0223 0.7165 -0.0686 0.069 Uiso 1 1 calc R . .
C11 C -0.1977(3) 0.5308(3) 0.0434(5) 0.0560(8) Uani 1 1 d . . .
H11A H -0.2725 0.5481 0.0659 0.067 Uiso 1 1 calc R . .
H11B H -0.2108 0.4781 -0.0346 0.067 Uiso 1 1 calc R . .
C4 C 0.7842(3) 0.6699(3) 0.4858(6) 0.0728(11) Uani 1 1 d . . .
H4A H 0.7813 0.7288 0.5348 0.109 Uiso 1 1 calc R . .
H4B H 0.8240 0.6718 0.3885 0.109 Uiso 1 1 calc R . .
H4C H 0.8264 0.6311 0.5830 0.109 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.05728(16) 0.06239(17) 0.03871(14) 0.00007(8) 0.01056(10) -0.00048(9)
S1 0.0554(5) 0.0815(6) 0.0445(5) -0.0077(4) 0.0163(4) 0.0032(4)
O2 0.0402(11) 0.0686(14) 0.0392(11) -0.0083(9) 0.0074(9) 0.0017(9)
O4 0.0575(14) 0.0798(17) 0.0518(13) 0.0145(12) 0.0060(11) -0.0228(12)
O3 0.0508(13) 0.0765(16) 0.0532(14) 0.0176(12) -0.0017(11) -0.0087(12)
O1 0.0556(14) 0.0973(19) 0.0454(13) -0.0181(13) 0.0092(11) 0.0091(13)
C2 0.0428(15) 0.0422(15) 0.0426(16) 0.0006(11) 0.0093(12) 0.0044(11)
C5 0.0387(14) 0.0531(17) 0.0380(15) -0.0060(12) 0.0089(12) 0.0017(12)
C9 0.0458(15) 0.0495(16) 0.0407(15) 0.0007(12) 0.0151(12) -0.0018(12)
C10 0.0515(16) 0.0568(17) 0.0334(14) 0.0054(12) 0.0125(12) 0.0018(14)
C3 0.0444(15) 0.0489(16) 0.0424(16) -0.0054(12) 0.0124(13) 0.0001(12)
C8 0.0432(15) 0.0534(17) 0.0414(16) 0.0037(13) 0.0074(13) 0.0035(13)
C1 0.0491(16) 0.0510(17) 0.0390(15) -0.0049(12) 0.0049(13) 0.0115(13)
C6 0.0498(17) 0.0558(19) 0.0568(19) 0.0097(15) 0.0132(15) -0.0053(14)
C7 0.0542(18) 0.062(2) 0.0519(19) 0.0200(16) 0.0080(15) -0.0004(15)
C11 0.0491(18) 0.067(2) 0.0487(18) -0.0024(15) 0.0077(14) -0.0068(15)
C4 0.060(2) 0.088(3) 0.077(3) -0.006(2) 0.031(2) -0.011(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 C2 2.096(3) . ?
S1 C1 1.731(4) . ?
S1 C4 1.793(4) . ?
O2 C3 1.355(4) . ?
O2 C5 1.406(4) . ?
O4 C9 1.370(4) . ?
O4 C11 1.417(4) . ?
O3 C8 1.377(4) . ?
O3 C11 1.421(4) . ?
O1 C3 1.191(4) . ?
C2 C1 1.336(5) . ?
C2 C3 1.470(4) . ?
C5 C6 1.371(4) . ?
C5 C10 1.387(4) . ?
C9 C10 1.364(4) . ?
C9 C8 1.376(4) . ?
C10 H10 0.9300 . ?
C8 C7 1.365(5) . ?
C1 H1 0.9300 . ?
C6 C7 1.404(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 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
C1 S1 C4 99.32(18) . . ?
C3 O2 C5 118.8(2) . . ?
C9 O4 C11 106.2(2) . . ?
C8 O3 C11 105.9(2) . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 I1 118.2(2) . . ?
C3 C2 I1 120.4(2) . . ?
C6 C5 C10 123.0(3) . . ?
C6 C5 O2 121.2(3) . . ?
C10 C5 O2 115.7(3) . . ?
C10 C9 O4 128.0(3) . . ?
C10 C9 C8 122.2(3) . . ?
O4 C9 C8 109.8(3) . . ?
C9 C10 C5 116.2(3) . . ?
C9 C10 H10 121.9 . . ?
C5 C10 H10 121.9 . . ?
O1 C3 O2 123.8(3) . . ?
O1 C3 C2 124.0(3) . . ?
O2 C3 C2 112.2(3) . . ?
C7 C8 C9 121.6(3) . . ?
C7 C8 O3 128.8(3) . . ?
C9 C8 O3 109.6(3) . . ?
C2 C1 S1 127.1(3) . . ?
C2 C1 H1 116.4 . . ?
S1 C1 H1 116.4 . . ?
C5 C6 C7 119.5(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 117.6(3) . . ?
C8 C7 H7 121.2 . . ?
C6 C7 H7 121.2 . . ?
O4 C11 O3 108.4(2) . . ?
O4 C11 H11A 110.0 . . ?
O3 C11 H11A 110.0 . . ?
O4 C11 H11B 110.0 . . ?
O3 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
S1 C4 H4A 109.5 . . ?
S1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
S1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

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
C3 O2 C5 C6 -67.8(4) . . . . ?
C3 O2 C5 C10 116.6(3) . . . . ?
C11 O4 C9 C10 -178.7(3) . . . . ?
C11 O4 C9 C8 2.3(4) . . . . ?
O4 C9 C10 C5 -179.1(3) . . . . ?
C8 C9 C10 C5 -0.2(5) . . . . ?
C6 C5 C10 C9 0.9(5) . . . . ?
O2 C5 C10 C9 176.4(3) . . . . ?
C5 O2 C3 O1 3.1(5) . . . . ?
C5 O2 C3 C2 -177.9(2) . . . . ?
C1 C2 C3 O1 17.0(5) . . . . ?
I1 C2 C3 O1 -162.5(3) . . . . ?
C1 C2 C3 O2 -162.0(3) . . . . ?
I1 C2 C3 O2 18.5(3) . . . . ?
C10 C9 C8 C7 -0.3(5) . . . . ?
O4 C9 C8 C7 178.7(3) . . . . ?
C10 C9 C8 O3 -178.9(3) . . . . ?
O4 C9 C8 O3 0.1(4) . . . . ?
C11 O3 C8 C7 179.0(4) . . . . ?
C11 O3 C8 C9 -2.5(4) . . . . ?
C3 C2 C1 S1 -1.1(4) . . . . ?
I1 C2 C1 S1 178.34(17) . . . . ?
C4 S1 C1 C2 165.1(3) . . . . ?
C10 C5 C6 C7 -0.9(5) . . . . ?
O2 C5 C6 C7 -176.2(3) . . . . ?
C9 C8 C7 C6 0.3(5) . . . . ?
O3 C8 C7 C6 178.6(3) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
C9 O4 C11 O3 -3.9(4) . . . . ?
C8 O3 C11 O4 3.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.41
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.229
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.072
