# Electronic Supplementary Material (ESI) for Green 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_mo_HJL_927_0m
_database_code_depnum_ccdc_archive 'CCDC 2069855'
loop_
_audit_author_name
_audit_author_address
La
;Southwest JiaoTong university
China
;
_audit_update_record             
;
2021-03-12 deposited with the CCDC.	2021-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 I O2 S'
_chemical_formula_sum            'C16 H15 I O2 S'
_chemical_formula_weight         398.24

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'

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

_cell_length_a                   5.4771(2)
_cell_length_b                   9.0324(4)
_cell_length_c                   31.6646(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1566.49(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.04

_exptl_crystal_description       bolck
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.176
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8920
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         3.422
_diffrn_reflns_theta_max         25.037
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             2771
_reflns_number_gt                2741
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.971

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0028P)²+0.3442P] 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 
;
 Flack x determined using 1098 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2771
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0152
_refine_ls_R_factor_gt           0.0149
_refine_ls_wR_factor_ref         0.0348
_refine_ls_wR_factor_gt          0.0346
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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 0.90782(4) 0.68402(2) 0.54134(2) 0.02601(7) Uani 1 1 d . . . . .
S1 S 0.38380(16) 0.55751(8) 0.65401(2) 0.02159(16) Uani 1 1 d . . . . .
O1 O 0.1776(4) 0.6551(3) 0.65842(7) 0.0307(5) Uani 1 1 d . . . . .
O2 O 0.3408(5) 0.4046(2) 0.64353(6) 0.0286(6) Uani 1 1 d . . . . .
C1 C 0.9423(8) 0.5563(4) 0.81876(11) 0.0413(9) Uani 1 1 d . . . . .
H3 H 0.8873 0.6391 0.8364 0.062 Uiso 1 1 calc R U . . .
H15 H 1.1184 0.5649 0.8138 0.062 Uiso 1 1 calc R U . . .
H1 H 0.9076 0.4627 0.8332 0.062 Uiso 1 1 calc R U . . .
C2 C 0.8099(7) 0.5600(3) 0.77715(10) 0.0266(7) Uani 1 1 d . . . . .
C3 C 0.8868(7) 0.4734(3) 0.74324(10) 0.0267(7) Uani 1 1 d . . . . .
H14 H 1.0282 0.4134 0.7462 0.032 Uiso 1 1 calc R U . . .
C4 C 0.7603(7) 0.4734(3) 0.70530(10) 0.0237(7) Uani 1 1 d . . . . .
H4 H 0.8138 0.4139 0.6824 0.028 Uiso 1 1 calc R U . . .
C5 C 0.5541(6) 0.5619(3) 0.70144(9) 0.0197(6) Uani 1 1 d . . . . .
C6 C 0.5846(7) 0.6433(3) 0.61673(9) 0.0203(6) Uani 1 1 d . . . . .
C7 C 0.6790(6) 0.5680(3) 0.58498(9) 0.0193(6) Uani 1 1 d . . . . .
C8 C 0.6556(6) 0.4083(3) 0.57323(9) 0.0191(7) Uani 1 1 d . . . . .
C9 C 0.8341(6) 0.3089(3) 0.58562(9) 0.0235(6) Uani 1 1 d . . . . .
H11 H 0.9699 0.3417 0.6018 0.028 Uiso 1 1 calc R U . . .
C10 C 0.8133(6) 0.1604(3) 0.57426(9) 0.0258(7) Uani 1 1 d . . . . .
H10 H 0.9343 0.0913 0.5829 0.031 Uiso 1 1 calc R U . . .
C11 C 0.6153(7) 0.1136(3) 0.55031(9) 0.0262(7) Uani 1 1 d . . . . .
H2 H 0.6006 0.0121 0.5428 0.031 Uiso 1 1 calc R U . . .
C12 C 0.6209(7) 0.8047(3) 0.62673(10) 0.0303(7) Uani 1 1 d . . . . .
H6 H 0.7857 0.8349 0.6182 0.045 Uiso 1 1 calc R U . . .
H7 H 0.6006 0.8206 0.6571 0.045 Uiso 1 1 calc R U . . .
H5 H 0.5002 0.8638 0.6113 0.045 Uiso 1 1 calc R U . . .
C13 C 0.4405(6) 0.2128(3) 0.53734(9) 0.0257(7) Uani 1 1 d . . . . .
H8 H 0.3067 0.1801 0.5207 0.031 Uiso 1 1 calc R U . . .
C14 C 0.4597(6) 0.3610(3) 0.54857(9) 0.0227(7) Uani 1 1 d . . . . .
H9 H 0.3397 0.4299 0.5395 0.027 Uiso 1 1 calc R U . . .
C15 C 0.4773(6) 0.6513(3) 0.73420(10) 0.0269(8) Uani 1 1 d . . . . .
H12 H 0.3389 0.7136 0.7309 0.032 Uiso 1 1 calc R U . . .
C16 C 0.6047(8) 0.6490(3) 0.77198(9) 0.0302(8) Uani 1 1 d . . . . .
H13 H 0.5511 0.7093 0.7948 0.036 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 2.140(3) . ?
S1 O1 1.440(2) . ?
S1 O2 1.440(2) . ?
S1 C5 1.768(3) . ?
S1 C6 1.790(3) . ?
C1 C2 1.505(5) . ?
C1 H3 0.9800 . ?
C1 H15 0.9800 . ?
C1 H1 0.9800 . ?
C2 C16 1.391(5) . ?
C2 C3 1.393(5) . ?
C3 C4 1.387(5) . ?
C3 H14 0.9500 . ?
C4 C5 1.389(5) . ?
C4 H4 0.9500 . ?
C5 C15 1.381(4) . ?
C6 C7 1.320(4) . ?
C6 C12 1.505(4) . ?
C7 C8 1.495(4) . ?
C8 C9 1.384(4) . ?
C8 C14 1.394(4) . ?
C9 C10 1.393(4) . ?
C9 H11 0.9500 . ?
C10 C11 1.389(5) . ?
C10 H10 0.9500 . ?
C11 C13 1.374(5) . ?
C11 H2 0.9500 . ?
C12 H6 0.9800 . ?
C12 H7 0.9800 . ?
C12 H5 0.9800 . ?
C13 C14 1.389(4) . ?
C13 H8 0.9500 . ?
C14 H9 0.9500 . ?
C15 C16 1.385(5) . ?
C15 H12 0.9500 . ?
C16 H13 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
O1 S1 O2 118.78(15) . . ?
O1 S1 C5 108.54(14) . . ?
O2 S1 C5 107.68(13) . . ?
O1 S1 C6 106.30(14) . . ?
O2 S1 C6 111.34(13) . . ?
C5 S1 C6 103.08(15) . . ?
C2 C1 H3 109.5 . . ?
C2 C1 H15 109.5 . . ?
H3 C1 H15 109.5 . . ?
C2 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
H15 C1 H1 109.5 . . ?
C16 C2 C3 118.5(3) . . ?
C16 C2 C1 120.3(3) . . ?
C3 C2 C1 121.1(3) . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H14 119.4 . . ?
C2 C3 H14 119.4 . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C15 C5 C4 121.2(3) . . ?
C15 C5 S1 119.4(2) . . ?
C4 C5 S1 119.4(2) . . ?
C7 C6 C12 127.4(3) . . ?
C7 C6 S1 121.3(2) . . ?
C12 C6 S1 111.2(2) . . ?
C6 C7 C8 130.8(3) . . ?
C6 C7 I1 118.0(2) . . ?
C8 C7 I1 111.23(19) . . ?
C9 C8 C14 120.3(3) . . ?
C9 C8 C7 119.6(3) . . ?
C14 C8 C7 120.1(3) . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H11 120.2 . . ?
C10 C9 H11 120.2 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C13 C11 C10 120.6(3) . . ?
C13 C11 H2 119.7 . . ?
C10 C11 H2 119.7 . . ?
C6 C12 H6 109.5 . . ?
C6 C12 H7 109.5 . . ?
H6 C12 H7 109.5 . . ?
C6 C12 H5 109.5 . . ?
H6 C12 H5 109.5 . . ?
H7 C12 H5 109.5 . . ?
C11 C13 C14 119.9(3) . . ?
C11 C13 H8 120.0 . . ?
C14 C13 H8 120.0 . . ?
C13 C14 C8 119.8(3) . . ?
C13 C14 H9 120.1 . . ?
C8 C14 H9 120.1 . . ?
C5 C15 C16 119.1(3) . . ?
C5 C15 H12 120.4 . . ?
C16 C15 H12 120.4 . . ?
C15 C16 C2 121.1(3) . . ?
C15 C16 H13 119.4 . . ?
C2 C16 H13 119.4 . . ?

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
C16 C2 C3 C4 -1.1(5) . . . . ?
C1 C2 C3 C4 178.0(3) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C15 1.4(5) . . . . ?
C3 C4 C5 S1 -177.5(2) . . . . ?
O1 S1 C5 C15 -0.4(3) . . . . ?
O2 S1 C5 C15 -130.2(3) . . . . ?
C6 S1 C5 C15 112.0(3) . . . . ?
O1 S1 C5 C4 178.5(2) . . . . ?
O2 S1 C5 C4 48.7(3) . . . . ?
C6 S1 C5 C4 -69.1(3) . . . . ?
O1 S1 C6 C7 -132.2(3) . . . . ?
O2 S1 C6 C7 -1.5(3) . . . . ?
C5 S1 C6 C7 113.7(3) . . . . ?
O1 S1 C6 C12 46.9(3) . . . . ?
O2 S1 C6 C12 177.6(2) . . . . ?
C5 S1 C6 C12 -67.2(3) . . . . ?
C12 C6 C7 C8 178.9(3) . . . . ?
S1 C6 C7 C8 -2.1(5) . . . . ?
C12 C6 C7 I1 -0.8(5) . . . . ?
S1 C6 C7 I1 178.14(17) . . . . ?
C6 C7 C8 C9 -96.3(4) . . . . ?
I1 C7 C8 C9 83.5(3) . . . . ?
C6 C7 C8 C14 86.1(4) . . . . ?
I1 C7 C8 C14 -94.1(3) . . . . ?
C14 C8 C9 C10 -1.8(4) . . . . ?
C7 C8 C9 C10 -179.3(3) . . . . ?
C8 C9 C10 C11 0.6(5) . . . . ?
C9 C10 C11 C13 0.6(5) . . . . ?
C10 C11 C13 C14 -0.7(5) . . . . ?
C11 C13 C14 C8 -0.4(5) . . . . ?
C9 C8 C14 C13 1.7(4) . . . . ?
C7 C8 C14 C13 179.2(3) . . . . ?
C4 C5 C15 C16 -1.9(5) . . . . ?
S1 C5 C15 C16 177.0(3) . . . . ?
C5 C15 C16 C2 0.9(5) . . . . ?
C3 C2 C16 C15 0.5(5) . . . . ?
C1 C2 C16 C15 -178.6(3) . . . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.048

_shelxl_version_number           2014/6

