# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shx97
_database_code_depnum_ccdc_archive 'CCDC 1474142'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 I O3 S'
_chemical_formula_sum            'C16 H15 I O3 S'
_chemical_formula_weight         414.24

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   12.094(2)
_cell_length_b                   9.4445(19)
_cell_length_c                   14.894(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.25(3)
_cell_angle_gamma                90.00
_cell_volume                     1624.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    12183
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.41
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    2.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_T_max  0.827
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean .
_diffrn_standards_number         image
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12839
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         25.34
_reflns_number_total             2967
_reflns_number_gt                2669
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_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)+(0.0452P)²+2.8316P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2967
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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 0.52113(3) 0.16517(3) 0.14416(3) 0.06562(16) Uani 1 1 d . . .
S1 S 0.35131(9) 0.11319(13) 0.30627(8) 0.0507(3) Uani 1 1 d . . .
O1 O 0.2696(3) 0.1821(4) 0.2283(2) 0.0656(9) Uani 1 1 d . . .
O2 O 0.3079(3) 0.0478(4) 0.3761(3) 0.0673(9) Uani 1 1 d . . .
O3 O 0.6320(3) -0.5421(4) 0.0987(3) 0.0671(9) Uani 1 1 d . . .
C1 C 0.6196(4) 0.3013(5) 0.4923(3) 0.0584(11) Uani 1 1 d . . .
H1A H 0.6751 0.2768 0.5482 0.070 Uiso 1 1 calc R . .
C2 C 0.5394(4) 0.2021(5) 0.4466(3) 0.0546(11) Uani 1 1 d . . .
H2A H 0.5408 0.1114 0.4712 0.065 Uiso 1 1 calc R . .
C3 C 0.4563(3) 0.2386(5) 0.3632(3) 0.0460(9) Uani 1 1 d . . .
C4 C 0.4533(5) 0.3718(5) 0.3265(4) 0.0603(12) Uani 1 1 d . . .
H4A H 0.3976 0.3962 0.2707 0.072 Uiso 1 1 calc R . .
C5 C 0.5362(5) 0.4713(5) 0.3749(4) 0.0693(13) Uani 1 1 d . . .
H5A H 0.5344 0.5623 0.3506 0.083 Uiso 1 1 calc R . .
C6 C 0.6193(4) 0.4379(5) 0.4567(3) 0.0562(11) Uani 1 1 d . . .
C7 C 0.7082(5) 0.5437(7) 0.5070(5) 0.0808(16) Uani 1 1 d . . .
H7A H 0.6953 0.6316 0.4730 0.121 Uiso 1 1 calc R . .
H7B H 0.7841 0.5087 0.5111 0.121 Uiso 1 1 calc R . .
H7C H 0.7023 0.5588 0.5692 0.121 Uiso 1 1 calc R . .
C8 C 0.6731(4) -0.2940(5) 0.1374(3) 0.0553(11) Uani 1 1 d . . .
H8A H 0.7472 -0.3004 0.1310 0.066 Uiso 1 1 calc R . .
C9 C 0.6341(4) -0.1669(5) 0.1609(4) 0.0557(11) Uani 1 1 d . . .
H9A H 0.6812 -0.0873 0.1679 0.067 Uiso 1 1 calc R . .
C10 C 0.5254(3) -0.1548(4) 0.1744(3) 0.0455(9) Uani 1 1 d . . .
C11 C 0.4557(3) -0.2747(5) 0.1592(3) 0.0494(10) Uani 1 1 d . . .
H11A H 0.3821 -0.2688 0.1664 0.059 Uiso 1 1 calc R . .
C12 C 0.4926(4) -0.4007(5) 0.1340(3) 0.0540(11) Uani 1 1 d . . .
H12A H 0.4441 -0.4793 0.1240 0.065 Uiso 1 1 calc R . .
C13 C 0.6031(4) -0.4120(5) 0.1231(3) 0.0498(10) Uani 1 1 d . . .
C14 C 0.7393(5) -0.5568(7) 0.0794(5) 0.0798(16) Uani 1 1 d . . .
H14A H 0.7491 -0.6534 0.0631 0.120 Uiso 1 1 calc R . .
H14C H 0.8012 -0.5308 0.1340 0.120 Uiso 1 1 calc R . .
H14D H 0.7403 -0.4962 0.0279 0.120 Uiso 1 1 calc R . .
C15 C 0.4825(3) -0.0228(4) 0.2043(3) 0.0449(9) Uani 1 1 d . . .
C16 C 0.4222(3) -0.0240(5) 0.2664(3) 0.0482(9) Uani 1 1 d . . .
H16A H 0.4171 -0.1121 0.2928 0.058 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 C15 2.102(4) . ?
S1 O2 1.437(3) . ?
S1 O1 1.438(3) . ?
S1 C16 1.752(4) . ?
S1 C3 1.759(5) . ?
O3 C13 1.356(5) . ?
O3 C14 1.417(6) . ?
C1 C2 1.375(7) . ?
C1 C6 1.394(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.390(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.368(7) . ?
C4 C5 1.407(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.367(8) . ?
C5 H5A 0.9300 . ?
C6 C7 1.496(7) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.372(6) . ?
C8 C13 1.378(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.393(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.389(6) . ?
C10 C15 1.470(6) . ?
C11 C12 1.362(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.398(6) . ?
C12 H12A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14C 0.9600 . ?
C14 H14D 0.9600 . ?
C15 C16 1.336(6) . ?
C16 H16A 0.9300 . ?

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
O2 S1 O1 117.9(2) . . ?
O2 S1 C16 104.4(2) . . ?
O1 S1 C16 110.4(2) . . ?
O2 S1 C3 107.9(2) . . ?
O1 S1 C3 108.0(2) . . ?
C16 S1 C3 107.78(19) . . ?
C13 O3 C14 117.9(4) . . ?
C2 C1 C6 121.3(5) . . ?
C2 C1 H1A 119.3 . . ?
C6 C1 H1A 119.3 . . ?
C1 C2 C3 119.4(4) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 S1 119.8(3) . . ?
C2 C3 S1 119.4(4) . . ?
C3 C4 C5 118.6(5) . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 H4A 120.7 . . ?
C6 C5 C4 121.8(5) . . ?
C6 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
C5 C6 C1 118.1(5) . . ?
C5 C6 C7 121.4(5) . . ?
C1 C6 C7 120.5(5) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 120.3(4) . . ?
C9 C8 H8A 119.8 . . ?
C13 C8 H8A 119.8 . . ?
C8 C9 C10 121.3(4) . . ?
C8 C9 H9A 119.3 . . ?
C10 C9 H9A 119.3 . . ?
C11 C10 C9 117.5(4) . . ?
C11 C10 C15 119.3(4) . . ?
C9 C10 C15 123.2(4) . . ?
C12 C11 C10 121.7(4) . . ?
C12 C11 H11A 119.2 . . ?
C10 C11 H11A 119.2 . . ?
C11 C12 C13 120.1(4) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
O3 C13 C8 125.4(4) . . ?
O3 C13 C12 115.6(4) . . ?
C8 C13 C12 119.0(4) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
O3 C14 H14D 109.5 . . ?
H14A C14 H14D 109.5 . . ?
H14C C14 H14D 109.5 . . ?
C16 C15 C10 121.1(4) . . ?
C16 C15 I1 122.6(3) . . ?
C10 C15 I1 116.4(3) . . ?
C15 C16 S1 130.6(4) . . ?
C15 C16 H16A 114.7 . . ?
S1 C16 H16A 114.7 . . ?

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
C6 C1 C2 C3 -0.1(7) . . . . ?
C1 C2 C3 C4 -0.2(7) . . . . ?
C1 C2 C3 S1 -178.3(3) . . . . ?
O2 S1 C3 C4 -132.7(4) . . . . ?
O1 S1 C3 C4 -4.2(4) . . . . ?
C16 S1 C3 C4 115.1(4) . . . . ?
O2 S1 C3 C2 45.4(4) . . . . ?
O1 S1 C3 C2 173.9(3) . . . . ?
C16 S1 C3 C2 -66.7(4) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
S1 C3 C4 C5 178.1(4) . . . . ?
C3 C4 C5 C6 0.4(8) . . . . ?
C4 C5 C6 C1 -0.6(8) . . . . ?
C4 C5 C6 C7 179.1(5) . . . . ?
C2 C1 C6 C5 0.5(7) . . . . ?
C2 C1 C6 C7 -179.2(5) . . . . ?
C13 C8 C9 C10 2.5(8) . . . . ?
C8 C9 C10 C11 -2.8(7) . . . . ?
C8 C9 C10 C15 176.8(5) . . . . ?
C9 C10 C11 C12 1.4(7) . . . . ?
C15 C10 C11 C12 -178.1(4) . . . . ?
C10 C11 C12 C13 0.2(7) . . . . ?
C14 O3 C13 C8 -4.9(7) . . . . ?
C14 O3 C13 C12 175.0(5) . . . . ?
C9 C8 C13 O3 179.2(5) . . . . ?
C9 C8 C13 C12 -0.7(7) . . . . ?
C11 C12 C13 O3 179.4(4) . . . . ?
C11 C12 C13 C8 -0.6(7) . . . . ?
C11 C10 C15 C16 39.6(6) . . . . ?
C9 C10 C15 C16 -140.0(5) . . . . ?
C11 C10 C15 I1 -140.4(4) . . . . ?
C9 C10 C15 I1 40.1(6) . . . . ?
C10 C15 C16 S1 -173.9(3) . . . . ?
I1 C15 C16 S1 6.1(6) . . . . ?
O2 S1 C16 C15 -177.0(4) . . . . ?
O1 S1 C16 C15 55.3(5) . . . . ?
C3 S1 C16 C15 -62.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.646
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.095
