# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H2 I2 N2 O2 S2'
_chemical_formula_weight         403.98

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'
N N 0.0061 0.0033 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   12.771(3)
_cell_length_b                   14.579(3)
_cell_length_c                   16.377(3)
_cell_angle_alpha                106.53(3)
_cell_angle_beta                 105.21(3)
_cell_angle_gamma                91.30(3)
_cell_volume                     2805.2(11)
_cell_formula_units_Z            18
_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_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    4.304
_exptl_crystal_F_000             3276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    10.685
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27551
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.115
_diffrn_reflns_theta_max         27.454
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             12545
_reflns_number_gt                9164
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12545
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.5924
_refine_ls_R_factor_gt           0.5622
_refine_ls_wR_factor_ref         0.8781
_refine_ls_wR_factor_gt          0.8534
_refine_ls_goodness_of_fit_ref   5.814
_refine_ls_restrained_S_all      5.814
_refine_ls_shift/su_max          0.888
_refine_ls_shift/su_mean         0.162

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 0.6162(2) 0.59055(18) -0.33084(18) 0.0654(12) Uani 1 1 d . . . . .
S1 S 0.5184(8) 0.8355(8) 0.1044(7) 0.063(2) Uani 1 1 d . . . . .
O4 O 0.498(2) 0.802(2) -0.1078(18) 0.068(7) Uani 1 1 d . . . . .
N1 N 0.463(2) 0.7520(18) 0.0082(16) 0.045(6) Uani 1 1 d . . . . .
O5 O -0.0715(17) 0.712(3) -0.020(2) 0.075(9) Uani 1 1 d . . . . .
C31 C 0.412(2) 0.600(3) -0.009(2) 0.049(8) Uani 1 1 d . . . . .
C30 C 0.016(3) 0.745(4) -0.127(2) 0.066(11) Uani 1 1 d . . . . .
C29 C 0.756(4) 0.871(3) -0.2602(18) 0.059(10) Uani 1 1 d . . . . .
O2 O 0.527(3) 0.795(3) 0.1736(19) 0.078(9) Uani 1 1 d . . . . .
C28 C 0.603(5) 0.782(4) -0.219(6) 0.12(3) Uani 1 1 d . . . . .
O3 O 0.452(4) 0.685(2) -0.240(3) 0.102(14) Uani 1 1 d . . . . .
C26 C 0.510(3) 0.660(3) -0.009(2) 0.065(11) Uani 1 1 d . . . . .
C25 C 0.661(5) 0.864(3) 0.113(4) 0.094(18) Uani 1 1 d . . . . .
C24 C 0.231(4) 0.774(3) -0.078(2) 0.064(11) Uani 1 1 d . . . . .
O1 O 0.454(5) 0.915(4) 0.094(4) 0.134(19) Uani 1 1 d . . . . .
C23 C 0.657(3) 0.746(4) -0.264(3) 0.068(12) Uani 1 1 d . . . . .
C22 C 0.625(4) 0.903(8) -0.168(3) 0.13(4) Uani 1 1 d . . . . .
C21 C 0.422(3) 0.785(4) -0.069(3) 0.070(11) Uani 1 1 d . . . . .
C20 C 0.721(3) 0.899(8) -0.193(3) 0.14(4) Uani 1 1 d . . . . .
C19 C 0.116(3) 0.753(3) -0.148(2) 0.056(9) Uani 1 1 d . . . . .
C18 C 0.382(4) 0.560(3) 0.038(3) 0.073(13) Uani 1 1 d . . . . .
C17 C 0.280(3) 0.498(2) 0.034(4) 0.084(17) Uani 1 1 d . . . . .
C16 C 0.519(2) 0.747(4) -0.179(2) 0.069(12) Uani 1 1 d . . . . .
C15 C 0.218(3) 0.739(2) -0.009(2) 0.051(8) Uani 1 1 d . . . . .
C14 C -0.186(3) 0.721(4) -0.081(3) 0.077(12) Uani 1 1 d . . . . .
C13 C 0.730(4) 0.797(7) -0.286(7) 0.19(4) Uani 1 1 d . . . . .
C12 C 0.319(3) 0.792(2) -0.1003(18) 0.054(9) Uani 1 1 d . . . . .
C11 C 0.345(4) 0.527(3) -0.115(3) 0.065(10) Uani 1 1 d . . . . .
C10 C 0.262(4) 0.469(4) -0.128(3) 0.071(11) Uani 1 1 d . . . . .
C9 C 0.013(3) 0.722(4) -0.057(3) 0.072(11) Uani 1 1 d . . . . .
C8 C 0.228(3) 0.460(4) -0.051(4) 0.073(13) Uani 1 1 d . . . . .
C7 C 0.117(3) 0.730(4) 0.014(3) 0.073(13) Uani 1 1 d . . . . .
C6 C 0.666(3) 0.952(4) 0.082(5) 0.094(19) Uani 1 1 d . . . . .
C5 C 0.739(6) 0.828(5) 0.142(4) 0.15(4) Uani 1 1 d . . . . .
C4 C 0.975(5) 0.965(4) 0.112(6) 0.12(3) Uani 1 1 d . . . . .
C3 C 0.853(4) 0.926(4) 0.119(5) 0.080(14) Uani 1 1 d . . . . .
C2 C 0.838(11) 0.871(5) 0.132(6) 0.25(8) Uani 1 1 d . . . . .
C1 C 0.787(2) 0.9679(18) 0.063(2) 0.039(6) 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 C23 2.21(5) . ?
S1 O1 1.46(4) . ?
S1 O2 1.40(3) . ?
S1 N1 1.66(3) . ?
S1 C25 1.81(5) . ?
O4 C16 1.31(5) . ?
O4 C21 1.36(4) . ?
N1 C21 1.45(5) . ?
N1 C26 1.47(5) . ?
O5 C9 1.39(4) . ?
O5 C14 1.57(4) . ?
C31 C18 1.22(5) . ?
C31 C26 1.50(4) . ?
C31 C11 1.73(6) . ?
C30 C9 1.29(5) . ?
C30 C19 1.42(5) . ?
C29 C13 1.04(10) . ?
C29 C20 1.26(7) . ?
C28 C23 1.16(8) . ?
C28 C22 1.70(12) . ?
C28 C16 1.53(7) . ?
O3 C16 1.25(6) . ?
C25 C5 1.20(10) . ?
C25 C6 1.51(6) . ?
C24 C12 1.31(6) . ?
C24 C15 1.41(5) . ?
C24 C19 1.56(5) . ?
C23 C13 1.36(4) . ?
C22 C20 1.39(7) . ?
C21 C12 1.30(6) . ?
C18 C17 1.55(6) . ?
C17 C8 1.32(8) . ?
C15 C7 1.45(5) . ?
C11 C10 1.28(7) . ?
C10 C8 1.47(7) . ?
C9 C7 1.49(6) . ?
C6 C1 1.67(5) . ?
C5 C2 1.46(19) . ?
C4 C3 1.68(7) . ?
C3 C1 1.36(7) . ?
C3 C2 0.91(14) . ?

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 124(3) . . ?
O1 S1 N1 101(3) . . ?
O2 S1 N1 109.5(19) . . ?
O1 S1 C25 112(3) . . ?
O2 S1 C25 102(2) . . ?
N1 S1 C25 108.5(19) . . ?
C16 O4 C21 129(4) . . ?
C21 N1 C26 116(3) . . ?
C21 N1 S1 117(3) . . ?
C26 N1 S1 118(2) . . ?
C9 O5 C14 113(3) . . ?
C18 C31 C26 140(4) . . ?
C18 C31 C11 103(4) . . ?
C26 C31 C11 112(3) . . ?
C9 C30 C19 121(3) . . ?
C13 C29 C20 105(7) . . ?
C23 C28 C22 120(4) . . ?
C23 C28 C16 136(5) . . ?
C22 C28 C16 104(5) . . ?
N1 C26 C31 96(3) . . ?
C5 C25 C6 123(4) . . ?
C5 C25 S1 130(4) . . ?
C6 C25 S1 107(4) . . ?
C12 C24 C15 130(3) . . ?
C12 C24 C19 121(3) . . ?
C15 C24 C19 105(4) . . ?
C28 C23 C13 123(7) . . ?
C28 C23 I1 116(4) . . ?
C13 C23 I1 120(6) . . ?
C20 C22 C28 86(7) . . ?
C12 C21 O4 123(3) . . ?
C12 C21 N1 122(3) . . ?
O4 C21 N1 115(3) . . ?
C29 C20 C22 142(5) . . ?
C30 C19 C24 124(3) . . ?
C31 C18 C17 138(4) . . ?
C8 C17 C18 106(5) . . ?
O3 C16 O4 124(3) . . ?
O3 C16 C28 108(4) . . ?
O4 C16 C28 122(5) . . ?
C24 C15 C7 126(3) . . ?
C29 C13 C23 128(9) . . ?
C21 C12 C24 134(3) . . ?
C10 C11 C31 121(4) . . ?
C11 C10 C8 119(4) . . ?
C30 C9 O5 132(4) . . ?
C30 C9 C7 119(3) . . ?
O5 C9 C7 107(3) . . ?
C17 C8 C10 128(4) . . ?
C15 C7 C9 118(3) . . ?
C25 C6 C1 111(3) . . ?
C2 C5 C25 111(5) . . ?
C1 C3 C2 128(8) . . ?
C1 C3 C4 99(5) . . ?
C2 C3 C4 127(10) . . ?
C5 C2 C3 134(10) . . ?
C3 C1 C6 102(3) . . ?

_refine_diff_density_max         42.926
_refine_diff_density_min         -4.516
_refine_diff_density_rms         1.064

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1010978'
