# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 I O4 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         506.33

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3045(3)
_cell_length_b                   10.2673(4)
_cell_length_c                   12.5079(5)
_cell_angle_alpha                86.7170(10)
_cell_angle_beta                 86.3770(10)
_cell_angle_gamma                82.0510(10)
_cell_volume                     1052.85(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      2.4802
_cell_measurement_theta_max      30.8645
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504

_exptl_absorpt_coefficient_mu    1.644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.80

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            22158
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_full        29.57
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_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.
;

_reflns_number_total             5928
_reflns_number_gt                5489
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0203
_refine_ls_wR_factor_gt          0.0486
_refine_ls_wR_factor_ref         0.0507
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_number_reflns         5928
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0218P)²+0.6399P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.006
_refine_diff_density_min         -0.371
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2011.6.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.386985(12) 0.71873(9) 0.389739(8) 0.02327(4) Uani d . 1 . .
S S1 1.26391(5) 0.54256(4) 0.62640(4) 0.03006(9) Uani d . 1 . .
O O1 0.33995(15) 1.01552(12) 0.40177(11) 0.0308(3) Uani d . 1 . .
O O2 1.21392(19) 0.65984(15) 0.55778(13) 0.0476(4) Uani d . 1 . .
O O3 1.38852(18) 0.56045(19) 0.69718(14) 0.0528(4) Uani d . 1 . .
O O4 1.30541(18) 0.42571(14) 0.56504(12) 0.0427(3) Uani d . 1 . .
C C1 0.17596(19) 0.85474(15) 0.37174(13) 0.0223(3) Uani d . 1 . .
C C2 0.0306(2) 0.81107(17) 0.35305(14) 0.0271(3) Uani d . 1 . .
H H2 0.0249 0.72 0.3473 0.033 Uiso calc R 1 . .
C C3 -0.1071(2) 0.90399(19) 0.34294(15) 0.0313(4) Uani d . 1 . .
H H3 -0.2087 0.877 0.3298 0.038 Uiso calc R 1 . .
C C4 -0.0953(2) 1.03607(18) 0.35210(15) 0.0304(4) Uani d . 1 . .
H H4 -0.1898 1.0989 0.3452 0.036 Uiso calc R 1 . .
C C5 0.0509(2) 1.07873(16) 0.37103(14) 0.0274(3) Uani d . 1 . .
H H5 0.0563 1.1699 0.3768 0.033 Uiso calc R 1 . .
C C6 0.1902(2) 0.98702(15) 0.38163(13) 0.0233(3) Uani d . 1 . .
C C7 0.3659(3) 1.15060(19) 0.3933(2) 0.0412(5) Uani d . 1 . .
H H7A 0.3344 1.1893 0.323 0.062 Uiso calc R 1 . .
H H7B 0.4813 1.1564 0.4013 0.062 Uiso calc R 1 . .
H H7C 0.2998 1.1987 0.4498 0.062 Uiso calc R 1 . .
C C8 1.0871(2) 0.51933(16) 0.70777(14) 0.0254(3) Uani d . 1 . .
C C9 1.1039(2) 0.4602(2) 0.80975(15) 0.0334(4) Uani d . 1 . .
H H9 1.209 0.4352 0.8363 0.04 Uiso calc R 1 . .
C C10 0.9656(3) 0.4378(2) 0.87269(16) 0.0380(4) Uani d . 1 . .
H H10 0.9768 0.3957 0.942 0.046 Uiso calc R 1 . .
C C11 0.8107(2) 0.47638(19) 0.83557(17) 0.0354(4) Uani d . 1 . .
C C12 0.7966(2) 0.53449(17) 0.73300(17) 0.0326(4) Uani d . 1 . .
H H12 0.6915 0.5608 0.7068 0.039 Uiso calc R 1 . .
C C13 0.9338(2) 0.55478(16) 0.66803(15) 0.0278(3) Uani d . 1 . .
H H13 0.9229 0.5924 0.5973 0.033 Uiso calc R 1 . .
C C14 0.6608(3) 0.4539(3) 0.9053(2) 0.0524(6) Uani d . 1 . .
H H14A 0.5705 0.5219 0.8872 0.079 Uiso calc R 1 . .
H H14B 0.6833 0.4583 0.9809 0.079 Uiso calc R 1 . .
H H14C 0.6314 0.367 0.8931 0.079 Uiso calc R 1 . .
C C15 0.5002(2) 0.78872(18) 0.25550(15) 0.0303(4) Uani d . 1 . .
C C16 0.5696(2) 0.83320(19) 0.17820(15) 0.0321(4) Uani d . 1 . .
C C17 0.6559(2) 0.8877(2) 0.08701(16) 0.0367(4) Uani d . 1 . .
C C18 0.6864(3) 1.0170(2) 0.08555(19) 0.0464(5) Uani d . 1 . .
H H18 0.6487 1.0705 0.1439 0.056 Uiso calc R 1 . .
C C19 0.7737(3) 1.0679(3) -0.0033(2) 0.0576(7) Uani d . 1 . .
H H19 0.7959 1.1564 -0.0052 0.069 Uiso calc R 1 . .
C C20 0.8272(3) 0.9899(3) -0.0879(2) 0.0591(7) Uani d . 1 . .
H H20 0.8857 1.0254 -0.1478 0.071 Uiso calc R 1 . .
C C21 0.7976(3) 0.8617(3) -0.08695(19) 0.0579(7) Uani d . 1 . .
H H21 0.8362 0.8086 -0.1454 0.069 Uiso calc R 1 . .
C C22 0.7110(3) 0.8106(3) -0.00009(17) 0.0481(5) Uani d . 1 . .
H H22 0.6887 0.7223 0.0004 0.058 Uiso calc R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C15 . 2.0172(19) ?
I1 C1 . 2.0997(15) ?
S1 O3 . 1.4407(17) ?
S1 O4 . 1.4508(15) ?
S1 O2 . 1.4654(14) ?
S1 C8 . 1.7688(17) ?
O1 C6 . 1.358(2) ?
O1 C7 . 1.430(2) ?
C1 C2 . 1.382(2) ?
C1 C6 . 1.393(2) ?
C2 C3 . 1.392(2) ?
C2 H2 . 0.95 ?
C3 C4 . 1.385(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.385(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.395(2) ?
C5 H5 . 0.95 ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
C8 C9 . 1.388(2) ?
C8 C13 . 1.390(2) ?
C9 C10 . 1.389(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.393(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.388(3) ?
C11 C14 . 1.511(3) ?
C12 C13 . 1.389(3) ?
C12 H12 . 0.95 ?
C13 H13 . 0.95 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C15 C16 . 1.195(3) ?
C16 C17 . 1.436(3) ?
C17 C18 . 1.384(3) ?
C17 C22 . 1.399(3) ?
C18 C19 . 1.405(3) ?
C18 H18 . 0.95 ?
C19 C20 . 1.377(4) ?
C19 H19 . 0.95 ?
C20 C21 . 1.371(4) ?
C20 H20 . 0.95 ?
C21 C22 . 1.383(3) ?
C21 H21 . 0.95 ?
C22 H22 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C15 I1 C1 . . 93.12(7) ?
O3 S1 O4 . . 112.68(10) ?
O3 S1 O2 . . 113.27(11) ?
O4 S1 O2 . . 111.97(10) ?
O3 S1 C8 . . 107.13(9) ?
O4 S1 C8 . . 106.64(9) ?
O2 S1 C8 . . 104.46(8) ?
C6 O1 C7 . . 117.87(14) ?
C2 C1 C6 . . 122.96(15) ?
C2 C1 I1 . . 119.92(12) ?
C6 C1 I1 . . 117.10(12) ?
C1 C2 C3 . . 118.27(16) ?
C1 C2 H2 . . 120.9 ?
C3 C2 H2 . . 120.9 ?
C4 C3 C2 . . 119.63(17) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C5 C4 C3 . . 121.62(16) ?
C5 C4 H4 . . 119.2 ?
C3 C4 H4 . . 119.2 ?
C4 C5 C6 . . 119.58(16) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
O1 C6 C1 . . 116.62(14) ?
O1 C6 C5 . . 125.46(15) ?
C1 C6 C5 . . 117.92(15) ?
O1 C7 H7A . . 109.5 ?
O1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
O1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C9 C8 C13 . . 120.58(16) ?
C9 C8 S1 . . 119.15(13) ?
C13 C8 S1 . . 120.21(13) ?
C8 C9 C10 . . 119.40(18) ?
C8 C9 H9 . . 120.3 ?
C10 C9 H9 . . 120.3 ?
C9 C10 C11 . . 120.86(19) ?
C9 C10 H10 . . 119.6 ?
C11 C10 H10 . . 119.6 ?
C12 C11 C10 . . 118.81(17) ?
C12 C11 C14 . . 120.6(2) ?
C10 C11 C14 . . 120.5(2) ?
C11 C12 C13 . . 121.06(17) ?
C11 C12 H12 . . 119.5 ?
C13 C12 H12 . . 119.5 ?
C12 C13 C8 . . 119.23(17) ?
C12 C13 H13 . . 120.4 ?
C8 C13 H13 . . 120.4 ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C16 C15 I1 . . 177.64(18) ?
C15 C16 C17 . . 178.6(2) ?
C18 C17 C22 . . 119.6(2) ?
C18 C17 C16 . . 119.9(2) ?
C22 C17 C16 . . 120.5(2) ?
C17 C18 C19 . . 119.1(2) ?
C17 C18 H18 . . 120.4 ?
C19 C18 H18 . . 120.4 ?
C20 C19 C18 . . 120.1(3) ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C21 C20 C19 . . 121.1(2) ?
C21 C20 H20 . . 119.5 ?
C19 C20 H20 . . 119.5 ?
C20 C21 C22 . . 119.3(3) ?
C20 C21 H21 . . 120.3 ?
C22 C21 H21 . . 120.3 ?
C21 C22 C17 . . 120.7(3) ?
C21 C22 H22 . . 119.7 ?
C17 C22 H22 . . 119.7 ?

_database_code_depnum_ccdc_archive 'CCDC 940260'
