# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_190319k
_database_code_depnum_ccdc_archive 'CCDC 1987676'
loop_
_audit_author_name
_audit_author_address
'Bo Jiang'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2020-03-03 deposited with the CCDC.	2020-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H26 I O3.50 S'
_chemical_formula_weight         565.44

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7830(9)
_cell_length_b                   12.3051(11)
_cell_length_c                   12.3219(12)
_cell_angle_alpha                62.4290(10)
_cell_angle_beta                 66.999(2)
_cell_angle_gamma                79.648(3)
_cell_volume                     1210.34(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2809
_cell_measurement_theta_min      2.431
_cell_measurement_theta_max      26.547

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             570
_exptl_absorpt_coefficient_mu    1.438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5639
_exptl_absorpt_correction_T_max  0.8351
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6047
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_sigmaI/netI    0.0662
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4149
_reflns_number_gt                3191
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.0763P)²+15.0792P] 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     SHELXL
_refine_ls_extinction_coef       0.0035(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4149
_refine_ls_number_parameters     299
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0900
_refine_ls_wR_factor_ref         0.2273
_refine_ls_wR_factor_gt          0.2178
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_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 0.10688(8) 0.23499(9) 0.24167(7) 0.0642(4) Uani 1 1 d . . .
O1 O 0.6877(9) 0.1112(7) 0.3156(7) 0.059(2) Uani 1 1 d . . .
O2 O 0.5543(8) -0.0151(7) 0.1765(7) 0.0545(18) Uani 1 1 d . . .
O3 O 0.4615(10) -0.1691(7) 0.4057(8) 0.064(2) Uani 1 1 d . . .
O4 O 0.905(3) 0.033(3) 0.254(3) 0.131(9) Uani 0.50 1 d PU . .
H4C H 0.8164 0.0587 0.2783 0.157 Uiso 0.50 1 d PR . .
H4D H 0.9626 0.0807 0.2489 0.157 Uiso 0.50 1 d PR . .
S1 S 0.4397(3) -0.0596(2) 0.3005(2) 0.0455(6) Uani 1 1 d . . .
C1 C 0.6326(11) 0.1702(9) 0.2304(10) 0.043(2) Uani 1 1 d . . .
C2 C 0.4612(10) 0.1842(9) 0.2618(9) 0.041(2) Uani 1 1 d . . .
C3 C 0.4493(10) 0.2482(9) 0.1266(9) 0.041(2) Uani 1 1 d . . .
C4 C 0.6013(10) 0.2846(9) 0.0302(9) 0.037(2) Uani 1 1 d . . .
C5 C 0.7062(10) 0.2398(9) 0.0910(10) 0.041(2) Uani 1 1 d . . .
C6 C 0.8555(11) 0.2638(10) 0.0243(12) 0.051(3) Uani 1 1 d . . .
H6 H 0.9233 0.2337 0.0675 0.061 Uiso 1 1 calc R . .
C7 C 0.9011(12) 0.3347(11) -0.1098(11) 0.057(3) Uani 1 1 d . . .
H7 H 1.0015 0.3519 -0.1580 0.068 Uiso 1 1 calc R . .
C8 C 0.7999(12) 0.3800(10) -0.1723(10) 0.050(2) Uani 1 1 d . . .
C9 C 0.6516(12) 0.3571(9) -0.1051(10) 0.049(2) Uani 1 1 d . . .
H9 H 0.5844 0.3895 -0.1489 0.058 Uiso 1 1 calc R . .
C10 C 0.8574(14) 0.4560(12) -0.3204(11) 0.066(3) Uani 1 1 d . . .
H10A H 0.9082 0.4035 -0.3621 0.099 Uiso 1 1 calc R . .
H10B H 0.9249 0.5174 -0.3433 0.099 Uiso 1 1 calc R . .
H10C H 0.7755 0.4949 -0.3488 0.099 Uiso 1 1 calc R . .
C11 C 0.3906(10) 0.0562(10) 0.3573(9) 0.043(2) Uani 1 1 d . . .
H11A H 0.2836 0.0657 0.3840 0.051 Uiso 1 1 calc R . .
H11B H 0.4161 0.0267 0.4349 0.051 Uiso 1 1 calc R . .
C12 C 0.4126(14) 0.2584(13) 0.3282(13) 0.067(3) Uani 1 1 d . . .
H12A H 0.4649 0.3351 0.2747 0.101 Uiso 1 1 calc R . .
H12B H 0.4315 0.2179 0.4088 0.101 Uiso 1 1 calc R . .
H12C H 0.3080 0.2731 0.3466 0.101 Uiso 1 1 calc R . .
C13 C 0.3250(10) 0.2763(9) 0.0975(9) 0.039(2) Uani 1 1 d . . .
C14 C 0.3139(10) 0.3416(9) -0.0364(9) 0.041(2) Uani 1 1 d . . .
C15 C 0.3486(12) 0.2833(10) -0.1144(10) 0.049(2) Uani 1 1 d . . .
H15 H 0.3737 0.2006 -0.0834 0.059 Uiso 1 1 calc R . .
C16 C 0.3464(12) 0.3479(10) -0.2403(10) 0.050(3) Uani 1 1 d . . .
H16 H 0.3750 0.3089 -0.2949 0.060 Uiso 1 1 calc R . .
C17 C 0.3027(12) 0.4693(11) -0.2865(10) 0.051(3) Uani 1 1 d . . .
C18 C 0.2642(13) 0.5244(11) -0.2054(11) 0.057(3) Uani 1 1 d . . .
H18 H 0.2331 0.6056 -0.2340 0.068 Uiso 1 1 calc R . .
C19 C 0.2703(12) 0.4618(10) -0.0812(12) 0.051(3) Uani 1 1 d . . .
H19 H 0.2445 0.5015 -0.0275 0.062 Uiso 1 1 calc R . .
C20 C 0.2956(17) 0.5375(15) -0.4217(12) 0.082(4) Uani 1 1 d . . .
H20A H 0.1985 0.5724 -0.4165 0.123 Uiso 1 1 calc R . .
H20B H 0.3150 0.4818 -0.4607 0.123 Uiso 1 1 calc R . .
H20C H 0.3686 0.6016 -0.4742 0.123 Uiso 1 1 calc R . .
C21 C 0.2804(11) -0.0820(10) 0.2774(10) 0.047(2) Uani 1 1 d . . .
C22 C 0.2799(12) -0.0503(10) 0.1573(11) 0.053(3) Uani 1 1 d . . .
H22 H 0.3656 -0.0185 0.0845 0.063 Uiso 1 1 calc R . .
C23 C 0.1533(14) -0.0647(12) 0.1413(12) 0.063(3) Uani 1 1 d . . .
H23 H 0.1553 -0.0441 0.0579 0.076 Uiso 1 1 calc R . .
C24 C 0.0228(13) -0.1095(11) 0.2481(13) 0.060(3) Uani 1 1 d . . .
C25 C 0.0280(14) -0.1404(15) 0.3703(15) 0.079(4) Uani 1 1 d . . .
H25 H -0.0576 -0.1705 0.4435 0.094 Uiso 1 1 calc R . .
C26 C 0.1553(13) -0.1281(13) 0.3876(12) 0.069(4) Uani 1 1 d . . .
H26 H 0.1562 -0.1503 0.4704 0.082 Uiso 1 1 calc R . .
C27 C -0.1148(16) -0.1194(16) 0.2336(19) 0.093(5) Uani 1 1 d . . .
H27A H -0.1071 -0.0709 0.1440 0.139 Uiso 1 1 calc R . .
H27B H -0.1960 -0.0902 0.2886 0.139 Uiso 1 1 calc R . .
H27C H -0.1317 -0.2036 0.2586 0.139 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 C13 2.135(9) . ?
O1 C1 1.231(11) . ?
O1 H4C 1.3202 . ?
O2 S1 1.413(8) . ?
O3 S1 1.427(8) . ?
O4 H4C 0.8499 . ?
O4 H4D 0.8500 . ?
S1 C21 1.777(10) . ?
S1 C11 1.779(11) . ?
C1 C5 1.448(14) . ?
C1 C2 1.563(13) . ?
C2 C12 1.400(14) . ?
C2 C3 1.521(13) . ?
C2 C11 1.544(14) . ?
C3 C13 1.343(13) . ?
C3 C4 1.480(13) . ?
C4 C5 1.391(13) . ?
C4 C9 1.399(13) . ?
C5 C6 1.374(14) . ?
C6 C7 1.385(16) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(16) . ?
C7 H7 0.9300 . ?
C8 C9 1.365(15) . ?
C8 C10 1.525(15) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.503(13) . ?
C14 C15 1.359(14) . ?
C14 C19 1.369(14) . ?
C15 C16 1.385(14) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(16) . ?
C16 H16 0.9300 . ?
C17 C18 1.356(16) . ?
C17 C20 1.503(15) . ?
C18 C19 1.379(16) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.347(15) . ?
C21 C26 1.379(15) . ?
C22 C23 1.381(16) . ?
C22 H22 0.9300 . ?
C23 C24 1.391(18) . ?
C23 H23 0.9300 . ?
C24 C25 1.391(19) . ?
C24 C27 1.458(16) . ?
C25 C26 1.387(17) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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 O1 H4C 115.4 . . ?
H4C O4 H4D 108.2 . . ?
O2 S1 O3 120.0(5) . . ?
O2 S1 C21 107.2(5) . . ?
O3 S1 C21 107.5(5) . . ?
O2 S1 C11 109.2(5) . . ?
O3 S1 C11 106.2(5) . . ?
C21 S1 C11 105.9(5) . . ?
O1 C1 C5 128.9(10) . . ?
O1 C1 C2 122.7(10) . . ?
C5 C1 C2 108.3(8) . . ?
C12 C2 C3 112.3(9) . . ?
C12 C2 C11 107.9(9) . . ?
C3 C2 C11 119.2(8) . . ?
C12 C2 C1 106.0(9) . . ?
C3 C2 C1 102.8(8) . . ?
C11 C2 C1 107.6(8) . . ?
C13 C3 C4 125.0(8) . . ?
C13 C3 C2 127.5(8) . . ?
C4 C3 C2 107.3(8) . . ?
C5 C4 C9 117.9(9) . . ?
C5 C4 C3 111.1(8) . . ?
C9 C4 C3 130.9(9) . . ?
C6 C5 C4 123.0(10) . . ?
C6 C5 C1 127.4(9) . . ?
C4 C5 C1 109.6(8) . . ?
C5 C6 C7 117.4(10) . . ?
C5 C6 H6 121.3 . . ?
C7 C6 H6 121.3 . . ?
C8 C7 C6 120.9(10) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 121.4(10) . . ?
C9 C8 C10 120.3(10) . . ?
C7 C8 C10 118.3(10) . . ?
C8 C9 C4 119.5(10) . . ?
C8 C9 H9 120.3 . . ?
C4 C9 H9 120.3 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 S1 117.6(7) . . ?
C2 C11 H11A 107.9 . . ?
S1 C11 H11A 107.9 . . ?
C2 C11 H11B 107.9 . . ?
S1 C11 H11B 107.9 . . ?
H11A C11 H11B 107.2 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C13 C14 127.2(8) . . ?
C3 C13 I1 123.5(7) . . ?
C14 C13 I1 109.2(6) . . ?
C15 C14 C19 119.5(9) . . ?
C15 C14 C13 120.8(9) . . ?
C19 C14 C13 119.7(9) . . ?
C14 C15 C16 119.5(10) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 121.3(10) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 118.0(10) . . ?
C18 C17 C20 121.1(12) . . ?
C16 C17 C20 121.0(11) . . ?
C17 C18 C19 121.1(10) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C14 C19 C18 120.5(10) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 121.5(10) . . ?
C22 C21 S1 121.5(8) . . ?
C26 C21 S1 116.9(8) . . ?
C21 C22 C23 120.5(10) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 120.9(11) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C25 116.7(11) . . ?
C23 C24 C27 122.2(13) . . ?
C25 C24 C27 121.1(13) . . ?
C26 C25 C24 122.9(12) . . ?
C26 C25 H25 118.6 . . ?
C24 C25 H25 118.6 . . ?
C21 C26 C25 117.5(11) . . ?
C21 C26 H26 121.2 . . ?
C25 C26 H26 121.2 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         2.271
_refine_diff_density_min         -1.050
_refine_diff_density_rms         0.174
