# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_tani2
_database_code_depnum_ccdc_archive 'CCDC 2121145'
_audit_update_record             
;
2021-11-09 deposited with the CCDC.	2023-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H5 I O S'
_chemical_formula_weight         264.07

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'

_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'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.519(2)
_cell_length_b                   14.285(2)
_cell_length_c                   5.349(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     803.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      14.5
_cell_measurement_theta_max      15.0

_exptl_crystal_description       prismatic
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    4.169
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.279
_exptl_absorpt_correction_T_max  0.558
_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        1.42
_diffrn_reflns_number            1092
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.404
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.596
_diffrn_reflns_point_group_measured_fraction_full 0.605
_reflns_number_total             1092
_reflns_number_gt                1024
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0333P)²+1.2935P] 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_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   -0.12(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1092
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0702
_refine_ls_wR_factor_gt          0.0690
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.174
_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 0.84691(4) 0.55910(3) -0.36175(8) 0.03472(14) Uani 1 1 d . . . . .
S1 S 0.92637(14) 0.67711(12) -0.0938(3) 0.0338(4) Uani 1 1 d . . . . .
O1 O 0.6850(4) 0.6671(3) 0.0419(10) 0.0376(11) Uani 1 1 d . . . . .
C1 C 0.7838(6) 0.7085(4) 0.0720(12) 0.0271(12) Uani 1 1 d . . . . .
C2 C 0.8033(6) 0.7869(4) 0.2523(12) 0.0275(12) Uani 1 1 d . . . . .
C3 C 0.7109(6) 0.7999(4) 0.4377(13) 0.0322(14) Uani 1 1 d . . . . .
H1 H 0.6393 0.7595 0.4459 0.039 Uiso 1 1 calc R U . . .
C4 C 0.7240(7) 0.8711(5) 0.6073(13) 0.0365(15) Uani 1 1 d . . . . .
H2 H 0.6604 0.8810 0.7305 0.044 Uiso 1 1 calc R U . . .
C5 C 0.8301(6) 0.9289(5) 0.5995(12) 0.0384(14) Uani 1 1 d . . . . .
H3 H 0.8400 0.9775 0.7192 0.046 Uiso 1 1 calc R U . . .
C6 C 0.9211(7) 0.9155(5) 0.4169(14) 0.0415(17) Uani 1 1 d . . . . .
H4 H 0.9932 0.9555 0.4112 0.050 Uiso 1 1 calc R U . . .
C7 C 0.9089(7) 0.8449(5) 0.2430(14) 0.0357(15) Uani 1 1 d . . . . .
H5 H 0.9721 0.8361 0.1183 0.043 Uiso 1 1 calc R U . . .

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 0.0435(2) 0.0291(2) 0.0316(2) -0.00168(18) -0.0007(2) -0.00496(18)
S1 0.0265(7) 0.0371(8) 0.0379(9) -0.0078(8) -0.0008(7) -0.0020(6)
O1 0.027(2) 0.040(2) 0.046(3) -0.004(2) 0.002(2) -0.006(2)
C1 0.027(3) 0.027(3) 0.027(3) 0.006(3) -0.006(2) -0.001(2)
C2 0.029(3) 0.026(3) 0.028(3) 0.002(3) -0.003(3) 0.000(2)
C3 0.027(3) 0.031(3) 0.038(3) 0.009(3) 0.001(3) 0.005(3)
C4 0.038(3) 0.042(3) 0.029(3) 0.001(3) -0.002(3) 0.009(3)
C5 0.046(4) 0.036(3) 0.034(3) -0.004(3) -0.001(3) 0.007(3)
C6 0.041(3) 0.037(3) 0.046(4) -0.008(3) 0.003(3) -0.012(3)
C7 0.034(3) 0.038(3) 0.035(3) -0.005(3) 0.000(3) -0.004(3)

_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 S1 2.3653(17) . ?
S1 C1 1.799(7) . ?
O1 C1 1.206(7) . ?
C1 C2 1.492(9) . ?
C2 C7 1.387(9) . ?
C2 C3 1.401(9) . ?
C3 C4 1.369(9) . ?
C3 H1 0.9500 . ?
C4 C5 1.388(10) . ?
C4 H2 0.9500 . ?
C5 C6 1.381(10) . ?
C5 H3 0.9500 . ?
C6 C7 1.378(10) . ?
C6 H4 0.9500 . ?
C7 H5 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
C1 S1 I1 100.5(2) . . ?
O1 C1 C2 124.9(6) . . ?
O1 C1 S1 122.0(5) . . ?
C2 C1 S1 113.0(4) . . ?
C7 C2 C3 120.1(6) . . ?
C7 C2 C1 122.4(6) . . ?
C3 C2 C1 117.5(6) . . ?
C4 C3 C2 119.9(6) . . ?
C4 C3 H1 120.1 . . ?
C2 C3 H1 120.1 . . ?
C3 C4 C5 120.2(7) . . ?
C3 C4 H2 119.9 . . ?
C5 C4 H2 119.9 . . ?
C6 C5 C4 119.7(6) . . ?
C6 C5 H3 120.1 . . ?
C4 C5 H3 120.1 . . ?
C7 C6 C5 121.0(7) . . ?
C7 C6 H4 119.5 . . ?
C5 C6 H4 119.5 . . ?
C6 C7 C2 119.2(7) . . ?
C6 C7 H5 120.4 . . ?
C2 C7 H5 120.4 . . ?

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 S1 C1 O1 4.8(6) . . . . ?
I1 S1 C1 C2 -177.4(4) . . . . ?
O1 C1 C2 C7 -165.9(7) . . . . ?
S1 C1 C2 C7 16.3(8) . . . . ?
O1 C1 C2 C3 15.0(10) . . . . ?
S1 C1 C2 C3 -162.8(5) . . . . ?
C7 C2 C3 C4 1.1(10) . . . . ?
C1 C2 C3 C4 -179.7(5) . . . . ?
C2 C3 C4 C5 -1.5(10) . . . . ?
C3 C4 C5 C6 1.3(10) . . . . ?
C4 C5 C6 C7 -0.6(11) . . . . ?
C5 C6 C7 C2 0.1(11) . . . . ?
C3 C2 C7 C6 -0.4(10) . . . . ?
C1 C2 C7 C6 -179.5(6) . . . . ?

_refine_diff_density_max         0.633
_refine_diff_density_min         -0.958
_refine_diff_density_rms         0.118

_shelx_res_file                  
;

    tani2.res created by SHELXL-2014/7

TITL PhC(O)SI
REM  Yadorkari-X generated
CELL 0.71070 10.5190 14.2850 5.3490 90.0000 90.0000 90.0000
ZERR 4.0 0.0020 0.0020 0.0020 0.0000 0.0000 0.0000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM 1/2+X, 1/2-Y, -Z
SYMM -X, 1/2+Y, 1/2-Z
REM  SPGR P212121 orthorhombic
SFAC C H I O S
UNIT 28 20 4 4 4
SIZE 0.40 0.29 0.14
TEMP -79.8
L.S. 10
FMAP 2
PLAN -20
ACTA
CONF
LIST 4
BOND $H
MERG 2
OMIT -10.000000 55.000000

WGHT    0.033300    1.293500
FVAR       1.20895
I1    3    0.846912    0.559097   -0.361747    11.00000    0.04350    0.02907 =
         0.03160   -0.00168   -0.00069   -0.00496
S1    5    0.926371    0.677107   -0.093807    11.00000    0.02647    0.03712 =
         0.03786   -0.00785   -0.00076   -0.00202
O1    4    0.684995    0.667108    0.041914    11.00000    0.02737    0.03983 =
         0.04572   -0.00386    0.00238   -0.00626
C1    1    0.783757    0.708477    0.072015    11.00000    0.02738    0.02734 =
         0.02665    0.00563   -0.00573   -0.00111
C2    1    0.803285    0.786875    0.252251    11.00000    0.02900    0.02557 =
         0.02792    0.00169   -0.00278    0.00046
C3    1    0.710903    0.799937    0.437737    11.00000    0.02698    0.03119 =
         0.03833    0.00906    0.00137    0.00476
AFIX  43
H1    2    0.639323    0.759499    0.445858    11.00000   -1.20000
AFIX   0
C4    1    0.724017    0.871116    0.607274    11.00000    0.03819    0.04235 =
         0.02894    0.00059   -0.00244    0.00932
AFIX  43
H2    2    0.660393    0.880981    0.730539    11.00000   -1.20000
AFIX   0
C5    1    0.830065    0.928894    0.599451    11.00000    0.04563    0.03599 =
         0.03352   -0.00438   -0.00125    0.00713
AFIX  43
H3    2    0.839956    0.977469    0.719185    11.00000   -1.20000
AFIX   0
C6    1    0.921129    0.915483    0.416928    11.00000    0.04149    0.03735 =
         0.04562   -0.00846    0.00334   -0.01209
AFIX  43
H4    2    0.993206    0.955497    0.411216    11.00000   -1.20000
AFIX   0
C7    1    0.908946    0.844908    0.243015    11.00000    0.03352    0.03815 =
         0.03536   -0.00490    0.00046   -0.00398
AFIX  43
H5    2    0.972120    0.836088    0.118298    11.00000   -1.20000

AFIX   0
HKLF 4

REM  PhC(O)SI
REM R1 =  0.0254 for    1024 Fo > 4sig(Fo)  and  0.0283 for all    1092 data
REM     91 parameters refined using      0 restraints

END

WGHT      0.0333      1.3130

REM Highest difference peak  0.633,  deepest hole -0.958,  1-sigma level  0.118
Q1    1   0.8497  0.5542 -0.1967  11.00000  0.05    0.63
Q2    1   0.8475  0.5644 -0.5369  11.00000  0.05    0.63
Q3    1   0.6792  0.8404  0.8462  11.00000  0.05    0.40
Q4    1   0.8174  1.0176  0.6283  11.00000  0.05    0.36
Q5    1   0.8820  1.0374  0.6167  11.00000  0.05    0.35
Q6    1   0.9139  0.6632  0.0833  11.00000  0.05    0.35
Q7    1   0.7032  0.8996  1.0454  11.00000  0.05    0.32
Q8    1   0.7769  0.7892  0.3793  11.00000  0.05    0.32
Q9    1   0.8322  1.0383  0.4626  11.00000  0.05    0.32
Q10   1   0.9186  0.4203 -0.4630  11.00000  0.05    0.31
Q11   1   0.8312  0.9407  0.8395  11.00000  0.05    0.30
Q12   1   0.7076  0.8608  0.4670  11.00000  0.05    0.29
Q13   1   0.7824  1.0021  0.8365  11.00000  0.05    0.29
Q14   1   0.9564  0.5942 -0.6264  11.00000  0.05    0.28
Q15   1   0.6506  0.9042  0.9205  11.00000  0.05    0.28
Q16   1   0.7906  0.8749  0.6286  11.00000  0.05    0.28
Q17   1   0.7475  0.8321  0.0028  11.00000  0.05    0.28
Q18   1   1.0536  0.5162 -0.2741  11.00000  0.05    0.27
Q19   1   0.8021  1.0548  0.7540  11.00000  0.05    0.27
Q20   1   0.6867  0.8216  0.3300  11.00000  0.05    0.26
;
_shelx_res_checksum              1475
