# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 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 
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#  except for the purpose of generating routine backup copies 
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#  data retrieval see:
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#  Bona fide researchers may freely download Mercury and enCIFer
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data_Compd1-MeI
_database_code_depnum_ccdc_archive 'CCDC 883531'
#TrackingRef 'web_deposit_cif_file_0_Yih-ChernHorng_1341977221.Crystal Structures_revised.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C67 H75 I1 N6 S6'
_chemical_formula_sum            'C67 H75 I1 N6 S6'
_chemical_formula_weight         1283.65

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'R -3 c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   17.8042(2)
_cell_length_b                   17.8042(2)
_cell_length_c                   47.6257(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     13074.2(4)
_cell_formula_units_Z            6
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4626
_cell_measurement_theta_min      2.623
_cell_measurement_theta_max      18.508

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.978
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4476
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8938
_exptl_absorpt_correction_T_max  0.9473
_exptl_absorpt_process_details   'SADABS, 2003 '

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(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 Kappa APEX2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26581
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2580
_reflns_number_gt                1320
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. During the structure refinement, the atoms of the one and
half Toluene solvent molecules were observed but could not
be modelled satisfactorily. The SQUEEZE routine in PLATON
was used to modify the HKL file.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1618P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         2580
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.2543
_refine_ls_wR_factor_gt          0.2291
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_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 0.3437(3) 0.0779(3) 0.04889(11) 0.0749(14) Uani 1 1 d . . .
C2 C 0.2645(4) 0.0101(5) 0.05406(15) 0.120(2) Uani 1 1 d . . .
H2 H 0.2430 -0.0020 0.0727 0.144 Uiso 1 1 calc R . .
C3 C 0.2133(4) -0.0428(4) 0.03188(16) 0.131(3) Uani 1 1 d . . .
H3 H 0.1598 -0.0939 0.0358 0.157 Uiso 1 1 calc R . .
C4 C 0.2396(3) -0.0212(3) 0.00512(13) 0.0917(16) Uani 1 1 d . . .
H4 H 0.2031 -0.0544 -0.0100 0.110 Uiso 1 1 calc R . .
C5 C 0.3194(3) 0.0488(3) -0.00006(11) 0.0802(14) Uani 1 1 d . . .
H5 H 0.3383 0.0631 -0.0190 0.096 Uiso 1 1 calc R . .
C6 C 0.3737(3) 0.0998(3) 0.02139(11) 0.0671(12) Uani 1 1 d . . .
C7 C 0.4871(3) 0.1915(3) -0.01140(9) 0.0687(13) Uani 1 1 d . . .
H7A H 0.4502 0.2100 -0.0214 0.082 Uiso 1 1 calc R . .
H7B H 0.4837 0.1416 -0.0217 0.082 Uiso 1 1 calc R . .
C8 C 0.5802(3) 0.2655(3) -0.01118(9) 0.0618(11) Uani 1 1 d . . .
C9 C 0.5981(3) 0.3513(3) -0.01080(9) 0.0627(12) Uani 1 1 d . . .
C10 C 0.5249(3) 0.3710(3) -0.00886(11) 0.0810(15) Uani 1 1 d . . .
H10A H 0.4764 0.3238 0.0017 0.097 Uiso 1 1 calc R . .
H10B H 0.5453 0.4253 0.0019 0.097 Uiso 1 1 calc R . .
C11 C 0.4935(4) 0.3801(5) -0.03509(16) 0.133(2) Uani 1 1 d . . .
H11A H 0.4475 0.3943 -0.0322 0.199 Uiso 1 1 calc R . .
H11B H 0.4702 0.3256 -0.0456 0.199 Uiso 1 1 calc R . .
H11C H 0.5410 0.4268 -0.0458 0.199 Uiso 1 1 calc R . .
I1 I 0.6667 0.3333 0.0617 0.0854(5) Uani 0.50 3 d SP . .
C12 C 0.6667 0.3333 0.1058 0.0854(5) Uani 0.50 3 d SP . .
H12' H 0.6410 0.2780 0.1140 0.102 Uiso 1 1 d R . .
N1 N 0.4555(2) 0.1657(2) 0.01632(8) 0.0799(12) Uani 1 1 d . . .
H1 H 0.4898 0.1931 0.0306 0.096 Uiso 1 1 calc R . .
S1 S 0.41206(10) 0.14211(9) 0.07746(3) 0.0939(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.062(3) 0.069(3) 0.077(4) 0.000(3) -0.008(3) 0.021(3)
C2 0.095(4) 0.119(5) 0.101(5) 0.010(4) -0.002(4) 0.020(4)
C3 0.084(4) 0.126(5) 0.117(6) 0.008(5) 0.014(4) 0.004(4)
C4 0.072(3) 0.081(4) 0.095(4) -0.001(3) -0.009(3) 0.018(3)
C5 0.073(3) 0.077(3) 0.079(4) -0.001(3) -0.009(3) 0.029(3)
C6 0.071(3) 0.056(3) 0.073(3) -0.001(2) -0.008(3) 0.031(3)
C7 0.065(3) 0.073(3) 0.065(3) -0.004(2) -0.015(2) 0.032(2)
C8 0.066(3) 0.065(3) 0.053(3) 0.005(2) 0.007(2) 0.031(2)
C9 0.069(3) 0.071(3) 0.055(3) 0.000(2) -0.001(2) 0.040(3)
C10 0.072(3) 0.079(3) 0.088(4) 0.008(3) -0.011(3) 0.035(3)
C11 0.124(5) 0.157(6) 0.136(6) 0.024(5) 0.003(4) 0.084(5)
I1 0.0964(7) 0.0964(7) 0.0634(8) 0.000 0.000 0.0482(3)
C12 0.0964(7) 0.0964(7) 0.0634(8) 0.000 0.000 0.0482(3)
N1 0.058(2) 0.078(3) 0.077(3) 0.004(2) 0.000(2) 0.013(2)
S1 0.1035(11) 0.0817(10) 0.0773(11) 0.0013(7) 0.0074(8) 0.0319(8)

_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 1.344(7) . ?
C1 C6 1.394(6) . ?
C1 S1 1.802(5) . ?
C2 C3 1.406(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.346(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.364(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(6) . ?
C5 H5 0.9500 . ?
C6 N1 1.360(5) . ?
C7 N1 1.418(5) . ?
C7 C8 1.517(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.397(6) . ?
C8 C9 1.416(6) 2_655 ?
C9 C8 1.416(6) 3_665 ?
C9 C10 1.512(6) . ?
C10 C11 1.411(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
I1 I1 2.0637 16_544 ?
I1 C12 2.1015 . ?
C12 I1 0.0378 16_544 ?
C12 H12' 0.9391 . ?
N1 H1 0.8800 . ?
S1 S1 2.033(3) 16_544 ?

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 C6 120.4(5) . . ?
C2 C1 S1 120.3(5) . . ?
C6 C1 S1 119.3(3) . . ?
C1 C2 C3 120.2(6) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.2(6) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.1(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 122.1(5) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
N1 C6 C5 122.0(5) . . ?
N1 C6 C1 120.2(4) . . ?
C5 C6 C1 117.7(4) . . ?
N1 C7 C8 111.0(4) . . ?
N1 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C9 120.4(4) . 2_655 ?
C9 C8 C7 120.1(4) . . ?
C9 C8 C7 119.4(4) 2_655 . ?
C8 C9 C8 119.6(4) . 3_665 ?
C8 C9 C10 120.2(4) . . ?
C8 C9 C10 120.2(4) 3_665 . ?
C11 C10 C9 114.1(5) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
I1 I1 C12 0.0 16_544 . ?
I1 C12 I1 0.1 16_544 . ?
I1 C12 H12' 114.5 16_544 . ?
I1 C12 H12' 114.6 . . ?
C6 N1 C7 121.6(4) . . ?
C6 N1 H1 119.2 . . ?
C7 N1 H1 119.2 . . ?
C1 S1 S1 103.98(17) . 16_544 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.072

# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.145 -0.141 -0.001 4525.1 836.3

_platon_squeeze_details          
; ?
;