# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_2j-1-x_auto
_database_code_depnum_ccdc_archive 'CCDC 2191403'
loop_
_audit_author_name
_audit_author_address
'Tao Cao'
;Nanjing University of Chinese Medicine
China
;
_audit_update_record             
;
2022-07-19 deposited with the CCDC.	2022-12-16 downloaded from the CCDC.
;
_audit_creation_date             2022-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         'C20 H19 I O6 S'
_chemical_formula_sum            'C20 H19 I O6 S'
_chemical_formula_weight         514.31
_chemical_absolute_configuration ab
_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 0.0181 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'
I I -0.3257 6.8362 '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'
S S 0.3331 0.5567 '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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.8727(9)
_cell_length_b                   7.4757(10)
_cell_length_c                   10.7012(13)
_cell_angle_alpha                75.161(12)
_cell_angle_beta                 88.164(11)
_cell_angle_gamma                77.878(12)
_cell_volume                     519.48(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1423
_cell_measurement_temperature    293
_cell_measurement_theta_max      63.2400
_cell_measurement_theta_min      4.2960
_shelx_estimated_absorpt_T_max   0.617
_shelx_estimated_absorpt_T_min   0.502
_exptl_absorpt_coefficient_mu    13.341
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1062
_diffrn_reflns_av_unetI/netI     0.1442
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3424
_diffrn_reflns_point_group_measured_fraction_full 0.579
_diffrn_reflns_point_group_measured_fraction_max 0.579
_diffrn_reflns_theta_full        63.656
_diffrn_reflns_theta_max         63.656
_diffrn_reflns_theta_min         4.275
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00  67.00   0.50    0.50    --   42.50 -77.00 120.00   80
  2  ω      3.00  69.00   0.50    0.50    --   42.50 -82.00 -60.00  132
  3  ω     19.00  64.00   0.50    0.50    --   42.50  65.00 -60.00   90
  4  ω    105.00 131.00   0.50    0.50    --   42.50   0.00-120.00   52
  5  ω     49.00  92.00   0.50    0.50    --   42.50   0.00-120.00   86
  6  ω    -29.00  -3.00   0.50    0.50    --   42.50   0.00-120.00   52
  7  ω      5.00  66.00   0.50    0.50    --   42.50 -65.00  90.00  122
  8  ω     72.00 130.00   0.50    0.50    --   42.50  65.00 -60.00  116
  9  ω     -6.00  64.00   0.50    0.50    --   42.50 -43.00 -30.00  140
 10  ω     16.00  76.00   0.50    0.50    --   42.50  54.00-120.00  120
 11  ω    -38.00 -10.00   0.50    0.50    --   42.50 -65.00  90.00   56
 12  ω    106.00 131.00   0.50    0.50    --   42.50  65.00-120.00   50
 13  ω     53.00 121.00   0.50    1.50    --   93.70 -82.00 -90.00  136
 14  ω     12.00  55.00   0.50    1.50    --   93.70 -33.00  60.00   86
 15  ω     62.00 111.00   0.50    1.50    --   93.70 -59.00-120.00   98
 16  ω     55.00 111.00   0.50    1.50    --   93.70 -50.00 120.00  112
 17  ω      7.00  54.00   0.50    1.50    --   93.70 -59.00-120.00   94
 18  ω     96.00 121.00   0.50    1.50    --   93.70 -33.00-120.00   50
 19  ω      4.00 183.00   0.50    1.50    --   93.70   0.00-180.00  358
 20  ω     72.00  98.00   0.50    1.50    --   93.70 -82.00 -30.00   52
 21  ω    157.00 182.00   0.50    1.50    --   93.70  82.00-180.00   50
 22  ω     69.00  98.00   0.50    1.50    --   93.70 -82.00  30.00   58
 23  ω      9.00  87.00   0.50    1.50    --   93.70 -33.00-120.00  156
 24  ω     97.00 123.00   0.50    1.50    --   93.70  82.00-180.00   52
 25  ω     70.00 107.00   0.50    1.50    --   93.70  77.00 120.00   74
 26  ω    139.00 182.00   0.50    1.50    --   93.70  77.00 120.00   86
 27  ω     41.00 120.00   0.50    1.50    --   93.70 -82.00  90.00  158
 28  ω     19.00  60.00   0.50    1.50    --   93.70 -82.00  30.00   82
 29  ω      6.00  31.00   0.50    1.50    --   93.70 -82.00  90.00   50
 30  ω     82.00 108.00   0.50    1.50    --   93.70 -82.00-150.00   52
 31  ω    133.00 180.00   0.50    1.50    --   93.70  68.00-180.00   94
 32  ω     74.00 125.00   0.50    1.50    --   93.70 -33.00  60.00  102
 33  ω     15.00  71.00   0.50    1.50    --   93.70 -82.00 150.00  112
 34  ω     75.00 118.00   0.50    1.50    --   93.70 -82.00 150.00   86
 35  ω      7.00  69.00   0.50    1.50    --   93.70 -82.00-120.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0073277000
_diffrn_orient_matrix_UB_12      -0.0826669000
_diffrn_orient_matrix_UB_13      -0.1183919000
_diffrn_orient_matrix_UB_21      0.0608966000
_diffrn_orient_matrix_UB_22      0.1786133000
_diffrn_orient_matrix_UB_23      -0.0849742000
_diffrn_orient_matrix_UB_31      0.2209822000
_diffrn_orient_matrix_UB_32      -0.0937272000
_diffrn_orient_matrix_UB_33      0.0309017000
_diffrn_oxdiff_digest_frames     
;
01bdac035c64b5589e7d5dbe8d65a69342034185b02
;
_diffrn_oxdiff_digest_hkl        
;
01c864c3232f283e816716e0f1e0c57e87bc5f
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.205
_reflns_Friedel_fraction_full    0.197
_reflns_Friedel_fraction_max     0.197
_reflns_number_gt                1636
_reflns_number_total             1979
_reflns_odcompleteness_completeness 95.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.917
_refine_diff_density_min         -1.382
_refine_diff_density_rms         0.199
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         1979
_refine_ls_number_restraints     117
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0875
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1839P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2120
_refine_ls_wR_factor_ref         0.2652
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.00(3)
 0.00(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20: within 2A with sigma of 0.004 and sigma for
terminal atoms of 0.008
4.a Ternary CH refined with riding coordinates:
 C8(H8)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
4.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
I1 I 0.34697(2) 0.15562(2) 0.53560(2) 0.0522(6) Uani 1 1 d . . . . .
S1 S 0.5107(11) 0.4503(10) 0.7315(7) 0.0416(16) Uani 1 1 d . . . . .
O1 O 0.558(4) 0.607(3) 0.766(2) 0.058(5) Uani 1 1 d . . . . .
O2 O 0.314(3) 0.410(3) 0.763(2) 0.047(5) Uani 1 1 d . . . . .
O3 O 0.126(3) 0.785(3) 0.563(2) 0.049(5) Uani 1 1 d . . . . .
O4 O 0.026(3) 0.547(3) 0.509(2) 0.059(6) Uani 1 1 d . . . . .
O5 O 0.263(5) 0.854(3) 0.284(3) 0.074(8) Uani 1 1 d . . . . .
O6 O 0.574(4) 0.784(3) 0.3490(19) 0.052(5) Uani 1 1 d . . . . .
C1 C 1.132(6) -0.249(5) 0.978(4) 0.067(6) Uani 1 1 d . U . . .
H1A H 1.076881 -0.320530 1.052812 0.101 Uiso 1 1 calc GR . . . .
H1B H 1.249592 -0.214982 1.002283 0.101 Uiso 1 1 calc GR . . . .
H1C H 1.165207 -0.323643 0.916305 0.101 Uiso 1 1 calc GR . . . .
C2 C 0.983(6) -0.075(4) 0.918(3) 0.056(4) Uani 1 1 d . U . . .
C3 C 0.778(5) -0.086(4) 0.903(3) 0.055(4) Uani 1 1 d . U . . .
H3 H 0.739133 -0.201328 0.930547 0.066 Uiso 1 1 calc R . . . .
C4 C 0.636(5) 0.081(4) 0.845(3) 0.053(4) Uani 1 1 d . U . . .
H4 H 0.501696 0.076591 0.841088 0.064 Uiso 1 1 calc R . . . .
C5 C 0.694(5) 0.241(4) 0.796(3) 0.051(4) Uani 1 1 d . U . . .
C6 C 0.887(5) 0.260(4) 0.805(3) 0.052(4) Uani 1 1 d . U . . .
H6 H 0.920930 0.377457 0.774579 0.063 Uiso 1 1 calc R . . . .
C7 C 1.032(5) 0.098(4) 0.861(3) 0.056(4) Uani 1 1 d . U . . .
H7 H 1.164507 0.107842 0.860179 0.067 Uiso 1 1 calc R . . . .
C8 C 0.539(5) 0.491(4) 0.561(3) 0.045(3) Uani 1 1 d . U . . .
H8 H 0.662645 0.533720 0.533568 0.054 Uiso 1 1 calc R . . . .
C9 C 0.366(5) 0.599(4) 0.469(3) 0.044(3) Uani 1 1 d . U . . .
C10 C 0.153(5) 0.632(4) 0.521(3) 0.043(4) Uani 1 1 d . U . . .
C11 C -0.075(6) 0.850(5) 0.607(4) 0.079(12) Uani 1 1 d . U . . .
H11A H -0.171439 0.826888 0.553378 0.118 Uiso 1 1 calc GR . . . .
H11B H -0.097017 0.983396 0.600656 0.118 Uiso 1 1 calc GR . . . .
H11C H -0.087795 0.782992 0.695025 0.118 Uiso 1 1 calc GR . . . .
C12 C 0.474(5) 0.406(4) 0.475(3) 0.046(3) Uani 1 1 d . U . . .
C13 C 0.396(5) 0.763(4) 0.359(3) 0.044(4) Uani 1 1 d . U . . .
C14 C 0.629(9) 0.914(5) 0.237(4) 0.090(16) Uani 1 1 d . U . . .
H14A H 0.593711 0.882258 0.160933 0.135 Uiso 1 1 calc GR . . . .
H14B H 0.769448 0.907504 0.240215 0.135 Uiso 1 1 calc GR . . . .
H14C H 0.559090 1.040421 0.236066 0.135 Uiso 1 1 calc GR . . . .
C15 C 0.598(5) 0.373(4) 0.353(3) 0.049(3) Uani 1 1 d . U . . .
C16 C 0.504(5) 0.422(4) 0.227(3) 0.052(3) Uani 1 1 d . U . . .
H16 H 0.365352 0.454911 0.221068 0.062 Uiso 1 1 calc R . . . .
C17 C 0.605(6) 0.421(5) 0.119(3) 0.054(3) Uani 1 1 d . U . . .
H17 H 0.543257 0.463945 0.037211 0.065 Uiso 1 1 calc R . . . .
C18 C 0.819(6) 0.349(4) 0.136(3) 0.056(3) Uani 1 1 d . U . . .
H18 H 0.894714 0.340080 0.063181 0.067 Uiso 1 1 calc R . . . .
C19 C 0.911(5) 0.294(4) 0.252(3) 0.055(3) Uani 1 1 d . U . . .
H19 H 1.045399 0.237125 0.260219 0.066 Uiso 1 1 calc R . . . .
C20 C 0.803(5) 0.323(4) 0.362(3) 0.051(3) Uani 1 1 d . U . . .
H20 H 0.869845 0.307611 0.439277 0.061 Uiso 1 1 calc R . . . .


_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 2.17(3) . ?
S1 O1 1.42(2) . ?
S1 O2 1.45(2) . ?
S1 C5 1.78(3) . ?
S1 C8 1.78(3) . ?
O3 C10 1.31(3) . ?
O3 C11 1.47(4) . ?
O4 C10 1.21(4) . ?
O5 C13 1.20(4) . ?
O6 C13 1.26(4) . ?
O6 C14 1.43(4) . ?
C1 C2 1.48(5) . ?
C2 C3 1.45(5) . ?
C2 C7 1.38(5) . ?
C3 C4 1.42(4) . ?
C4 C5 1.32(4) . ?
C5 C6 1.37(5) . ?
C6 C7 1.41(4) . ?
C8 C9 1.52(4) . ?
C8 C12 1.38(5) . ?
C9 C10 1.54(4) . ?
C9 C12 1.46(4) . ?
C9 C13 1.52(4) . ?
C12 C15 1.58(4) . ?
C15 C16 1.44(4) . ?
C15 C20 1.38(5) . ?
C16 C17 1.34(4) . ?
C17 C18 1.45(5) . ?
C18 C19 1.34(5) . ?
C19 C20 1.41(4) . ?

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 117.9(14) . . ?
O1 S1 C5 110.4(15) . . ?
O1 S1 C8 106.7(14) . . ?
O2 S1 C5 108.7(14) . . ?
O2 S1 C8 108.3(15) . . ?
C8 S1 C5 103.9(15) . . ?
C10 O3 C11 116(3) . . ?
C13 O6 C14 119(3) . . ?
C3 C2 C1 120(3) . . ?
C7 C2 C1 124(3) . . ?
C7 C2 C3 116(3) . . ?
C4 C3 C2 120(3) . . ?
C5 C4 C3 120(3) . . ?
C4 C5 S1 119(2) . . ?
C4 C5 C6 123(3) . . ?
C6 C5 S1 118(2) . . ?
C5 C6 C7 119(3) . . ?
C2 C7 C6 122(3) . . ?
C9 C8 S1 121(2) . . ?
C12 C8 S1 130(3) . . ?
C12 C8 C9 60(2) . . ?
C8 C9 C10 120(2) . . ?
C12 C9 C8 55(2) . . ?
C12 C9 C10 120(2) . . ?
C12 C9 C13 121(2) . . ?
C13 C9 C8 119(3) . . ?
C13 C9 C10 112(2) . . ?
O3 C10 C9 108(2) . . ?
O4 C10 O3 126(3) . . ?
O4 C10 C9 126(2) . . ?
C8 C12 I1 123(2) . . ?
C8 C12 C9 65(2) . . ?
C8 C12 C15 122(3) . . ?
C9 C12 I1 125(2) . . ?
C9 C12 C15 117(2) . . ?
C15 C12 I1 103.1(17) . . ?
O5 C13 O6 124(3) . . ?
O5 C13 C9 121(3) . . ?
O6 C13 C9 114(3) . . ?
C16 C15 C12 121(3) . . ?
C20 C15 C12 120(3) . . ?
C20 C15 C16 118(3) . . ?
C17 C16 C15 123(3) . . ?
C16 C17 C18 116(3) . . ?
C19 C18 C17 123(3) . . ?
C18 C19 C20 120(3) . . ?
C15 C20 C19 119(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.126
_oxdiff_exptl_absorpt_empirical_full_min 0.528
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.00(3)
2 0.00(3)

