# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_g:\140605e\work\mo_140605e_0m
_database_code_depnum_ccdc_archive 'CCDC 1410882'
_audit_update_record             
;
2015-07-06 deposited with the CCDC.
2015-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 I2 O4 S2'
_chemical_formula_weight         590.21

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.5162(5)
_cell_length_b                   7.9870(5)
_cell_length_c                   27.2258(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.3900(10)
_cell_angle_gamma                90.00
_cell_volume                     1848.63(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      31.88

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    2.121
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    3.646
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.6688
_exptl_absorpt_correction_T_max  0.7119
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16431
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         29.99
_reflns_number_total             5351
_reflns_number_gt                4991
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0514P)²+4.4268P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5351
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0773
_refine_ls_goodness_of_fit_ref   1.255
_refine_ls_restrained_S_all      1.255
_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
C1 C 0.3604(4) -0.0009(4) 0.27101(12) 0.0125(6) Uani 1 1 d . . .
C2 C 0.2732(4) 0.1372(4) 0.26084(12) 0.0111(6) Uani 1 1 d . . .
C3 C 0.2145(4) 0.1435(4) 0.21062(13) 0.0125(6) Uani 1 1 d . . .
C4 C 0.2638(4) 0.0118(4) 0.18242(12) 0.0111(6) Uani 1 1 d . . .
C5 C 0.1788(5) 0.4117(5) 0.27062(14) 0.0202(7) Uani 1 1 d . . .
H5A H 0.2675 0.4735 0.2572 0.024 Uiso 1 1 calc R . .
H5B H 0.1310 0.4840 0.2952 0.024 Uiso 1 1 calc R . .
C6 C 0.0584(5) 0.3702(5) 0.22983(14) 0.0179(7) Uani 1 1 d . . .
H6A H -0.0289 0.3070 0.2435 0.021 Uiso 1 1 calc R . .
H6B H 0.0146 0.4754 0.2155 0.021 Uiso 1 1 calc R . .
C7 C 0.2329(4) -0.0099(4) 0.12795(12) 0.0112(6) Uani 1 1 d . . .
H7 H 0.1373 0.0580 0.1183 0.013 Uiso 1 1 calc R . .
C8 C 0.3650(4) 0.0591(4) 0.09947(12) 0.0117(6) Uani 1 1 d . . .
C9 C 0.3492(4) 0.1674(4) 0.06088(12) 0.0117(6) Uani 1 1 d . . .
C10 C 0.4921(4) 0.1993(4) 0.03751(12) 0.0121(6) Uani 1 1 d . . .
C11 C 0.6179(4) 0.1164(4) 0.06001(13) 0.0125(6) Uani 1 1 d . . .
C12 C 0.2391(4) 0.3879(5) 0.01554(14) 0.0162(7) Uani 1 1 d . . .
H12A H 0.2855 0.4770 0.0371 0.019 Uiso 1 1 calc R . .
H12B H 0.1384 0.4302 0.0003 0.019 Uiso 1 1 calc R . .
C13 C 0.3493(4) 0.3479(5) -0.02396(13) 0.0150(6) Uani 1 1 d . . .
H13A H 0.3062 0.2541 -0.0444 0.018 Uiso 1 1 calc R . .
H13B H 0.3594 0.4466 -0.0456 0.018 Uiso 1 1 calc R . .
C14 C 0.1958(4) -0.1916(4) 0.11216(13) 0.0132(6) Uani 1 1 d . . .
H14A H 0.1856 -0.1970 0.0758 0.016 Uiso 1 1 calc R . .
H14B H 0.2850 -0.2643 0.1235 0.016 Uiso 1 1 calc R . .
C15 C 0.0456(4) -0.2587(5) 0.13264(13) 0.0157(6) Uani 1 1 d . . .
H15A H 0.0599 -0.2656 0.1689 0.019 Uiso 1 1 calc R . .
H15B H -0.0417 -0.1799 0.1244 0.019 Uiso 1 1 calc R . .
C16 C 0.0022(5) -0.4306(5) 0.11221(15) 0.0215(8) Uani 1 1 d . . .
H16A H -0.0040 -0.4264 0.0762 0.032 Uiso 1 1 calc R . .
H16B H -0.1000 -0.4644 0.1237 0.032 Uiso 1 1 calc R . .
H16C H 0.0825 -0.5120 0.1236 0.032 Uiso 1 1 calc R . .
I1 I 0.46558(3) -0.06835(3) 0.338324(9) 0.01937(8) Uani 1 1 d . . .
I2 I 0.85114(3) 0.14086(3) 0.044907(9) 0.01620(8) Uani 1 1 d . . .
O1 O 0.2367(3) 0.2565(3) 0.29415(9) 0.0157(5) Uani 1 1 d . . .
O2 O 0.1246(3) 0.2716(3) 0.19120(10) 0.0163(5) Uani 1 1 d . . .
O3 O 0.2095(3) 0.2402(3) 0.04483(10) 0.0158(5) Uani 1 1 d . . .
O4 O 0.5023(3) 0.3024(3) -0.00213(10) 0.0158(5) Uani 1 1 d . . .
S1 S 0.37662(10) -0.12454(10) 0.21941(3) 0.01314(16) Uani 1 1 d . . .
S2 S 0.55927(10) -0.00342(11) 0.10852(3) 0.01379(16) Uani 1 1 d . . .


_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
C1 C2 1.349(5) . ?
C1 S1 1.729(3) . ?
C1 I1 2.063(3) . ?
C2 O1 1.364(4) . ?
C2 C3 1.429(5) . ?
C3 O2 1.365(4) . ?
C3 C4 1.382(5) . ?
C4 C7 1.501(5) . ?
C4 S1 1.735(3) . ?
C5 O1 1.467(5) . ?
C5 C6 1.503(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O2 1.454(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.508(5) . ?
C7 C14 1.541(5) . ?
C7 H7 1.0000 . ?
C8 C9 1.362(5) . ?
C8 S2 1.732(4) . ?
C9 O3 1.372(4) . ?
C9 C10 1.429(5) . ?
C10 O4 1.364(4) . ?
C10 C11 1.372(5) . ?
C11 S2 1.728(4) . ?
C11 I2 2.062(3) . ?
C12 O3 1.455(4) . ?
C12 C13 1.503(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O4 1.446(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.523(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.519(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C2 C1 S1 111.7(2) . . ?
C2 C1 I1 126.9(3) . . ?
S1 C1 I1 121.40(19) . . ?
C1 C2 O1 125.4(3) . . ?
C1 C2 C3 112.5(3) . . ?
O1 C2 C3 122.1(3) . . ?
O2 C3 C4 122.5(3) . . ?
O2 C3 C2 123.6(3) . . ?
C4 C3 C2 113.8(3) . . ?
C3 C4 C7 126.6(3) . . ?
C3 C4 S1 109.3(2) . . ?
C7 C4 S1 124.0(3) . . ?
O1 C5 C6 109.5(3) . . ?
O1 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
O1 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
O2 C6 C5 112.2(3) . . ?
O2 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
O2 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C4 C7 C8 111.9(3) . . ?
C4 C7 C14 113.9(3) . . ?
C8 C7 C14 110.3(3) . . ?
C4 C7 H7 106.7 . . ?
C8 C7 H7 106.7 . . ?
C14 C7 H7 106.7 . . ?
C9 C8 C7 125.9(3) . . ?
C9 C8 S2 110.0(3) . . ?
C7 C8 S2 123.9(3) . . ?
C8 C9 O3 124.0(3) . . ?
C8 C9 C10 114.1(3) . . ?
O3 C9 C10 121.9(3) . . ?
O4 C10 C11 124.1(3) . . ?
O4 C10 C9 123.7(3) . . ?
C11 C10 C9 112.2(3) . . ?
C10 C11 S2 110.8(3) . . ?
C10 C11 I2 126.9(3) . . ?
S2 C11 I2 122.01(19) . . ?
O3 C12 C13 110.8(3) . . ?
O3 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
O4 C13 C12 110.2(3) . . ?
O4 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
O4 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C15 C14 C7 113.1(3) . . ?
C15 C14 H14A 109.0 . . ?
C7 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C7 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 112.1(3) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 O1 C5 112.6(3) . . ?
C3 O2 C6 111.0(3) . . ?
C9 O3 C12 110.1(3) . . ?
C10 O4 C13 112.3(3) . . ?
C1 S1 C4 92.57(17) . . ?
C11 S2 C8 92.77(17) . . ?

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
S1 C1 C2 O1 178.5(3) . . . . ?
I1 C1 C2 O1 -1.3(5) . . . . ?
S1 C1 C2 C3 1.3(4) . . . . ?
I1 C1 C2 C3 -178.5(2) . . . . ?
C1 C2 C3 O2 -179.3(3) . . . . ?
O1 C2 C3 O2 3.4(5) . . . . ?
C1 C2 C3 C4 -2.6(4) . . . . ?
O1 C2 C3 C4 -179.9(3) . . . . ?
O2 C3 C4 C7 1.9(6) . . . . ?
C2 C3 C4 C7 -174.9(3) . . . . ?
O2 C3 C4 S1 179.4(3) . . . . ?
C2 C3 C4 S1 2.6(4) . . . . ?
O1 C5 C6 O2 -62.6(4) . . . . ?
C3 C4 C7 C8 93.5(4) . . . . ?
S1 C4 C7 C8 -83.6(4) . . . . ?
C3 C4 C7 C14 -140.5(3) . . . . ?
S1 C4 C7 C14 42.4(4) . . . . ?
C4 C7 C8 C9 -129.1(4) . . . . ?
C14 C7 C8 C9 102.9(4) . . . . ?
C4 C7 C8 S2 56.5(4) . . . . ?
C14 C7 C8 S2 -71.5(4) . . . . ?
C7 C8 C9 O3 5.5(6) . . . . ?
S2 C8 C9 O3 -179.4(3) . . . . ?
C7 C8 C9 C10 -174.0(3) . . . . ?
S2 C8 C9 C10 1.1(4) . . . . ?
C8 C9 C10 O4 179.3(3) . . . . ?
O3 C9 C10 O4 -0.2(5) . . . . ?
C8 C9 C10 C11 -1.7(4) . . . . ?
O3 C9 C10 C11 178.9(3) . . . . ?
O4 C10 C11 S2 -179.5(3) . . . . ?
C9 C10 C11 S2 1.4(4) . . . . ?
O4 C10 C11 I2 6.0(5) . . . . ?
C9 C10 C11 I2 -173.1(2) . . . . ?
O3 C12 C13 O4 -65.0(4) . . . . ?
C4 C7 C14 C15 63.3(4) . . . . ?
C8 C7 C14 C15 -169.9(3) . . . . ?
C7 C14 C15 C16 173.8(3) . . . . ?
C1 C2 O1 C5 164.3(4) . . . . ?
C3 C2 O1 C5 -18.8(5) . . . . ?
C6 C5 O1 C2 46.4(4) . . . . ?
C4 C3 O2 C6 166.3(3) . . . . ?
C2 C3 O2 C6 -17.3(5) . . . . ?
C5 C6 O2 C3 46.2(4) . . . . ?
C8 C9 O3 C12 160.5(3) . . . . ?
C10 C9 O3 C12 -20.0(4) . . . . ?
C13 C12 O3 C9 51.2(4) . . . . ?
C11 C10 O4 C13 169.1(3) . . . . ?
C9 C10 O4 C13 -11.9(5) . . . . ?
C12 C13 O4 C10 42.6(4) . . . . ?
C2 C1 S1 C4 0.1(3) . . . . ?
I1 C1 S1 C4 180.0(2) . . . . ?
C3 C4 S1 C1 -1.6(3) . . . . ?
C7 C4 S1 C1 176.0(3) . . . . ?
C10 C11 S2 C8 -0.7(3) . . . . ?
I2 C11 S2 C8 174.1(2) . . . . ?
C9 C8 S2 C11 -0.2(3) . . . . ?
C7 C8 S2 C11 175.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H16C O2 0.98 2.54 3.332(5) 138.3 1_545

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         2.054
_refine_diff_density_min         -1.137
_refine_diff_density_rms         0.209
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_22
_database_code_depnum_ccdc_archive 'CCDC 1410883'
_audit_update_record             
;
2015-07-06 deposited with the CCDC.
2015-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H14 I2 O4 S2'
_chemical_formula_weight         624.22

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           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_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                   16.0830(7)
_cell_length_b                   16.083
_cell_length_c                   7.8168(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2021.92(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.051
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1192
_exptl_absorpt_coefficient_mu    3.340
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7590
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2340
_reflns_number_gt                2304
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0000P)²+0.2270P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2340
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0188
_refine_ls_R_factor_gt           0.0184
_refine_ls_wR_factor_ref         0.0440
_refine_ls_wR_factor_gt          0.0438
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.058963(17) 0.259811(18) 1.00025(4) 0.03473(8) Uani 1 1 d . . .
I2 I -0.309196(17) 0.633698(19) 1.46803(5) 0.04649(11) Uani 1 1 d . . .
S2 S -0.14450(5) 0.51199(6) 1.47822(13) 0.0257(2) Uani 1 1 d . . .
S1 S 0.05818(6) 0.40115(7) 1.31049(13) 0.0289(2) Uani 1 1 d . . .
O4 O -0.20722(17) 0.6597(2) 1.8501(4) 0.0379(8) Uani 1 1 d . . .
C17 C -0.1523(3) 0.6787(3) 1.9916(7) 0.0429(11) Uani 1 1 d . . .
H17A H -0.1845 0.7013 2.0856 0.051 Uiso 1 1 calc R . .
H17B H -0.1124 0.7205 1.9562 0.051 Uiso 1 1 calc R . .
C19 C -0.2055(2) 0.5837(3) 1.5838(5) 0.0276(9) Uani 1 1 d . . .
C2 C -0.0340(2) 0.2734(3) 1.3405(5) 0.0228(8) Uani 1 1 d . . .
C14 C -0.0727(2) 0.5101(2) 1.6424(5) 0.0204(7) Uani 1 1 d . . .
C15 C -0.0971(2) 0.5606(3) 1.7716(5) 0.0238(8) Uani 1 1 d . . .
C5 C -0.0454(2) 0.3208(2) 1.4922(5) 0.0233(7) Uani 1 1 d . . .
C6 C -0.00003(19) 0.3916(2) 1.4981(5) 0.0217(7) Uani 1 1 d . . .
O1 O -0.07197(16) 0.19859(19) 1.3120(4) 0.0284(6) Uani 1 1 d . . .
O3 O -0.05394(17) 0.5699(2) 1.9205(4) 0.0327(7) Uani 1 1 d . . .
O2 O -0.09730(17) 0.2958(2) 1.6205(4) 0.0290(7) Uani 1 1 d . . .
C1 C 0.0197(2) 0.3090(3) 1.2297(5) 0.0259(9) Uani 1 1 d . . .
C18 C -0.1727(2) 0.6044(3) 1.7377(5) 0.0251(9) Uani 1 1 d . . .
C3 C -0.1390(3) 0.1843(4) 1.4332(7) 0.0555(17) Uani 1 1 d . . .
H3A H -0.1884 0.2128 1.3929 0.067 Uiso 1 1 calc R . .
H3B H -0.1513 0.1253 1.4362 0.067 Uiso 1 1 calc R . .
C4 C -0.1211(4) 0.2114(4) 1.6000(7) 0.0553(16) Uani 1 1 d . . .
H4A H -0.0769 0.1768 1.6450 0.066 Uiso 1 1 calc R . .
H4B H -0.1700 0.2017 1.6701 0.066 Uiso 1 1 calc R . .
C9 C 0.0932(2) 0.5702(2) 1.5169(5) 0.0252(8) Uani 1 1 d . . .
H9 H 0.0495 0.5847 1.4450 0.030 Uiso 1 1 calc R . .
C10 C 0.1682(2) 0.6136(2) 1.5091(6) 0.0267(8) Uani 1 1 d . . .
H10 H 0.1740 0.6581 1.4340 0.032 Uiso 1 1 calc R . .
C8 C 0.0842(2) 0.5052(3) 1.6329(5) 0.0214(8) Uani 1 1 d . . .
C13 C 0.1512(2) 0.4841(3) 1.7366(5) 0.0300(9) Uani 1 1 d . . .
H13 H 0.1460 0.4407 1.8144 0.036 Uiso 1 1 calc R . .
C12 C 0.2254(3) 0.5269(3) 1.7253(6) 0.0331(10) Uani 1 1 d . . .
H12 H 0.2698 0.5119 1.7949 0.040 Uiso 1 1 calc R . .
C7 C 0.0037(2) 0.4540(3) 1.6398(5) 0.0240(8) Uani 1 1 d . . .
H7 H 0.0041 0.4230 1.7477 0.029 Uiso 1 1 calc R . .
C11 C 0.2338(2) 0.5905(3) 1.6132(5) 0.0279(9) Uani 1 1 d . . .
H11 H 0.2841 0.6189 1.6061 0.033 Uiso 1 1 calc R . .
C16 C -0.1070(3) 0.6029(3) 2.0505(5) 0.0425(12) Uani 1 1 d . . .
H16A H -0.0740 0.6166 2.1503 0.051 Uiso 1 1 calc R . .
H16B H -0.1471 0.5608 2.0838 0.051 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 C1 2.059(4) . ?
I2 C19 2.061(4) . ?
S2 C19 1.724(4) . ?
S2 C14 1.726(4) . ?
S1 C1 1.726(4) . ?
S1 C6 1.746(4) . ?
O4 C18 1.368(5) . ?
O4 C17 1.448(6) . ?
C17 C16 1.493(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 C18 1.355(6) . ?
C2 C1 1.350(5) . ?
C2 O1 1.368(5) . ?
C2 C5 1.421(6) . ?
C14 C15 1.354(5) . ?
C14 C7 1.524(5) . ?
C15 O3 1.364(5) . ?
C15 C18 1.430(5) . ?
C5 C6 1.353(5) . ?
C5 O2 1.366(5) . ?
C6 C7 1.496(5) . ?
O1 C3 1.453(5) . ?
O3 C16 1.429(5) . ?
O2 C4 1.419(6) . ?
C3 C4 1.404(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C9 C8 1.392(6) . ?
C9 C10 1.394(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(5) . ?
C10 H10 0.9300 . ?
C8 C13 1.390(5) . ?
C8 C7 1.536(5) . ?
C13 C12 1.380(6) . ?
C13 H13 0.9300 . ?
C12 C11 1.354(7) . ?
C12 H12 0.9300 . ?
C7 H7 0.9800 . ?
C11 H11 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
C19 S2 C14 92.09(18) . . ?
C1 S1 C6 92.27(19) . . ?
C18 O4 C17 112.3(3) . . ?
O4 C17 C16 111.1(4) . . ?
O4 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
O4 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C18 C19 S2 111.6(3) . . ?
C18 C19 I2 127.5(3) . . ?
S2 C19 I2 120.7(2) . . ?
C1 C2 O1 123.7(4) . . ?
C1 C2 C5 113.0(4) . . ?
O1 C2 C5 123.3(3) . . ?
C15 C14 C7 126.8(3) . . ?
C15 C14 S2 110.5(3) . . ?
C7 C14 S2 122.7(3) . . ?
C14 C15 O3 123.8(4) . . ?
C14 C15 C18 113.8(4) . . ?
O3 C15 C18 122.4(4) . . ?
C6 C5 O2 123.5(4) . . ?
C6 C5 C2 114.2(4) . . ?
O2 C5 C2 122.3(3) . . ?
C5 C6 C7 127.7(4) . . ?
C5 C6 S1 109.5(3) . . ?
C7 C6 S1 122.8(3) . . ?
C2 O1 C3 111.4(3) . . ?
C15 O3 C16 110.1(3) . . ?
C5 O2 C4 111.3(3) . . ?
C2 C1 S1 111.0(3) . . ?
C2 C1 I1 126.3(3) . . ?
S1 C1 I1 122.6(2) . . ?
C19 C18 O4 124.9(4) . . ?
C19 C18 C15 112.0(4) . . ?
O4 C18 C15 123.1(4) . . ?
C4 C3 O1 113.9(4) . . ?
C4 C3 H3A 108.8 . . ?
O1 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
O1 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 O2 117.2(5) . . ?
C3 C4 H4A 108.0 . . ?
O2 C4 H4A 108.0 . . ?
C3 C4 H4B 108.0 . . ?
O2 C4 H4B 108.0 . . ?
H4A C4 H4B 107.2 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C13 C8 C9 118.9(4) . . ?
C13 C8 C7 120.2(4) . . ?
C9 C8 C7 120.9(3) . . ?
C12 C13 C8 120.7(4) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C6 C7 C14 112.0(3) . . ?
C6 C7 C8 111.5(3) . . ?
C14 C7 C8 111.3(3) . . ?
C6 C7 H7 107.2 . . ?
C14 C7 H7 107.2 . . ?
C8 C7 H7 107.2 . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
O3 C16 C17 112.0(4) . . ?
O3 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
O3 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?

_diffrn_measured_fraction_theta_max 0.571
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.567
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.048
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1410884'
_audit_update_record             
;
2015-07-06 deposited with the CCDC.
2015-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 I2 O4 S2'
_chemical_formula_weight         674.28

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   16.947(2)
_cell_length_b                   9.1615(13)
_cell_length_c                   15.240(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.051(4)
_cell_angle_gamma                90.00
_cell_volume                     2273.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.970
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    2.978
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21053
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         28.35
_reflns_number_total             5642
_reflns_number_gt                3338
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0895P)²+15.2460P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5642
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1349
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_ref         0.2114
_refine_ls_wR_factor_gt          0.1838
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.59318(5) 0.35579(10) -0.08155(5) 0.0591(3) Uani 1 1 d . . .
I2 I 1.08442(4) 0.04868(10) 0.25658(5) 0.0595(3) Uani 1 1 d . . .
S2 S 0.88459(13) -0.0032(3) 0.21009(15) 0.0360(5) Uani 1 1 d . . .
S1 S 0.71527(13) 0.1978(3) 0.10058(16) 0.0350(5) Uani 1 1 d . . .
C1 C 0.6169(5) 0.2513(10) 0.0421(6) 0.033(2) Uani 1 1 d . . .
C2 C 0.5620(5) 0.2066(10) 0.0829(6) 0.034(2) Uani 1 1 d . . .
C3 C 0.4363(9) 0.161(3) 0.1069(15) 0.138(10) Uani 1 1 d . . .
H3A H 0.4059 0.2378 0.1271 0.166 Uiso 1 1 calc R . .
H3B H 0.3956 0.1002 0.0657 0.166 Uiso 1 1 calc R . .
C4 C 0.4666(7) 0.083(2) 0.1770(11) 0.112(7) Uani 1 1 d . . .
H4A H 0.4441 -0.0144 0.1625 0.135 Uiso 1 1 calc R . .
H4B H 0.4446 0.1200 0.2250 0.135 Uiso 1 1 calc R . .
C5 C 0.5981(5) 0.1253(10) 0.1647(6) 0.0308(19) Uani 1 1 d . . .
C6 C 0.6809(5) 0.1142(10) 0.1840(6) 0.0284(18) Uani 1 1 d . . .
C7 C 0.7332(5) 0.0185(10) 0.2584(5) 0.0274(18) Uani 1 1 d . . .
H7 H 0.7170 0.0395 0.3141 0.033 Uiso 1 1 calc R . .
C8 C 0.8240(5) 0.0528(10) 0.2793(5) 0.0285(18) Uani 1 1 d . . .
C9 C 0.8719(5) 0.1192(9) 0.3547(5) 0.0270(17) Uani 1 1 d . . .
C10 C 0.9103(6) 0.1842(14) 0.5080(7) 0.053(3) Uani 1 1 d . . .
H10A H 0.9276 0.0879 0.5321 0.063 Uiso 1 1 calc R . .
H10B H 0.8908 0.2369 0.5532 0.063 Uiso 1 1 calc R . .
C11 C 0.9800(7) 0.2619(16) 0.4909(9) 0.068(4) Uani 1 1 d . . .
H11A H 0.9620 0.3576 0.4660 0.082 Uiso 1 1 calc R . .
H11B H 1.0218 0.2758 0.5483 0.082 Uiso 1 1 calc R . .
C12 C 0.9570(5) 0.1266(10) 0.3578(6) 0.035(2) Uani 1 1 d . . .
C13 C 0.9730(5) 0.0647(11) 0.2840(6) 0.034(2) Uani 1 1 d . . .
C14 C 0.7194(5) -0.1436(10) 0.2399(6) 0.0281(18) Uani 1 1 d . . .
C15 C 0.6833(6) -0.1933(11) 0.1552(6) 0.038(2) Uani 1 1 d . . .
H15 H 0.6663 -0.1272 0.1074 0.046 Uiso 1 1 calc R . .
C16 C 0.6706(7) -0.3452(12) 0.1375(7) 0.046(3) Uani 1 1 d . . .
H16 H 0.6458 -0.3773 0.0784 0.055 Uiso 1 1 calc R . .
C17 C 0.6940(6) -0.4415(11) 0.2050(7) 0.043(2) Uani 1 1 d . . .
H17 H 0.6858 -0.5407 0.1927 0.051 Uiso 1 1 calc R . .
C18 C 0.7309(5) -0.3948(10) 0.2943(6) 0.034(2) Uani 1 1 d . . .
C19 C 0.7561(6) -0.4948(13) 0.3674(8) 0.051(3) Uani 1 1 d . . .
H19 H 0.7484 -0.5941 0.3558 0.061 Uiso 1 1 calc R . .
C20 C 0.7912(7) -0.4496(14) 0.4538(8) 0.056(3) Uani 1 1 d . . .
H20 H 0.8088 -0.5181 0.5001 0.067 Uiso 1 1 calc R . .
C21 C 0.8011(6) -0.3030(13) 0.4738(6) 0.045(3) Uani 1 1 d . . .
H21 H 0.8237 -0.2735 0.5339 0.055 Uiso 1 1 calc R . .
C22 C 0.7780(5) -0.1992(11) 0.4058(6) 0.034(2) Uani 1 1 d . . .
H22 H 0.7855 -0.1005 0.4200 0.041 Uiso 1 1 calc R . .
C23 C 0.7426(4) -0.2441(10) 0.3136(6) 0.0280(18) Uani 1 1 d . . .
O1 O 0.4791(4) 0.2307(9) 0.0521(5) 0.0497(19) Uani 1 1 d . . .
O3 O 0.8439(4) 0.1707(7) 0.4241(4) 0.0377(15) Uani 1 1 d . . .
O2 O 0.5530(4) 0.0657(8) 0.2162(4) 0.0436(17) Uani 1 1 d . . .
O4 O 1.0155(4) 0.1844(9) 0.4280(5) 0.053(2) Uani 1 1 d . . .


_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 C1 2.051(9) . ?
I2 C13 2.049(8) . ?
S2 C13 1.723(9) . ?
S2 C8 1.740(8) . ?
S1 C6 1.719(8) . ?
S1 C1 1.730(8) . ?
C1 C2 1.319(13) . ?
C2 O1 1.370(10) . ?
C2 C5 1.436(12) . ?
C3 C4 1.271(18) . ?
C3 O1 1.402(16) . ?
C4 O2 1.429(13) . ?
C5 O2 1.352(10) . ?
C5 C6 1.355(11) . ?
C6 C7 1.512(11) . ?
C7 C8 1.516(11) . ?
C7 C14 1.518(12) . ?
C8 C9 1.353(12) . ?
C9 O3 1.358(10) . ?
C9 C12 1.433(11) . ?
C10 O3 1.456(11) . ?
C10 C11 1.464(17) . ?
C11 O4 1.450(14) . ?
C12 O4 1.349(11) . ?
C12 C13 1.352(13) . ?
C14 C15 1.345(12) . ?
C14 C23 1.421(12) . ?
C15 C16 1.422(15) . ?
C16 C17 1.330(15) . ?
C17 C18 1.398(14) . ?
C18 C23 1.414(13) . ?
C18 C19 1.415(14) . ?
C19 C20 1.350(17) . ?
C20 C21 1.377(17) . ?
C21 C22 1.381(13) . ?
C22 C23 1.427(12) . ?

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
C13 S2 C8 92.8(4) . . ?
C6 S1 C1 91.8(4) . . ?
C2 C1 S1 111.9(7) . . ?
C2 C1 I1 126.4(6) . . ?
S1 C1 I1 121.4(5) . . ?
C1 C2 O1 125.3(8) . . ?
C1 C2 C5 112.6(8) . . ?
O1 C2 C5 122.0(8) . . ?
C4 C3 O1 127.0(12) . . ?
C3 C4 O2 122.9(12) . . ?
O2 C5 C6 124.1(8) . . ?
O2 C5 C2 122.7(7) . . ?
C6 C5 C2 113.2(8) . . ?
C5 C6 C7 124.3(8) . . ?
C5 C6 S1 110.4(6) . . ?
C7 C6 S1 124.4(6) . . ?
C6 C7 C8 112.8(7) . . ?
C6 C7 C14 113.6(7) . . ?
C8 C7 C14 109.7(7) . . ?
C9 C8 C7 127.3(7) . . ?
C9 C8 S2 109.4(6) . . ?
C7 C8 S2 123.1(6) . . ?
C8 C9 O3 124.2(7) . . ?
C8 C9 C12 114.3(7) . . ?
O3 C9 C12 121.5(7) . . ?
O3 C10 C11 110.5(10) . . ?
O4 C11 C10 112.5(10) . . ?
O4 C12 C13 123.5(8) . . ?
O4 C12 C9 123.9(8) . . ?
C13 C12 C9 112.6(8) . . ?
C12 C13 S2 111.0(6) . . ?
C12 C13 I2 127.4(6) . . ?
S2 C13 I2 121.6(5) . . ?
C15 C14 C23 119.5(8) . . ?
C15 C14 C7 121.0(8) . . ?
C23 C14 C7 119.4(7) . . ?
C14 C15 C16 121.2(9) . . ?
C17 C16 C15 120.3(9) . . ?
C16 C17 C18 120.4(10) . . ?
C17 C18 C23 120.1(8) . . ?
C17 C18 C19 121.6(10) . . ?
C23 C18 C19 118.3(9) . . ?
C20 C19 C18 121.7(11) . . ?
C19 C20 C21 120.6(10) . . ?
C20 C21 C22 120.9(10) . . ?
C21 C22 C23 119.7(10) . . ?
C18 C23 C14 118.3(8) . . ?
C18 C23 C22 118.9(8) . . ?
C14 C23 C22 122.8(8) . . ?
C2 O1 C3 112.0(8) . . ?
C9 O3 C10 111.3(7) . . ?
C5 O2 C4 113.0(8) . . ?
C12 O4 C11 111.6(7) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.35
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.312
_refine_diff_density_min         -1.864
_refine_diff_density_rms         0.187
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_properties_physical    Heat-sensitive
