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


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Yih-Chern Horng'
_publ_contact_author_email       ychorng@cc.ncue.edu.tw
loop_
_publ_author_name
'Pin-Shen Huang'
'Chih-Hong Kuo'
'Chang-Chih Hsieh'
'Yih-Chern Horng'

data_1-I2
_database_code_depnum_ccdc_archive 'CCDC 848479'
#TrackingRef 'web_deposit_cif_file_0_Yih-ChernHorng_1326272386.1-I2.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C66 H72 N6 S6, I2'
_chemical_formula_sum            'C66 H72 I2 N6 S6'
_chemical_melting_point          ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?

_diffrn_ambient_temperature      200(2)
_chemical_formula_weight         1395.46

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'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'R -3 c'
_symmetry_int_tables_number      167
_chemical_absolute_configuration ?

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                   17.583(3)
_cell_length_b                   17.583(3)
_cell_length_c                   48.345(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     12943(4)
_cell_formula_units_Z            6
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2293
_cell_measurement_theta_min      3.92
_cell_measurement_theta_max      18.26
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.074
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4272
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6909
_exptl_absorpt_correction_T_max  0.8323
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
;
The R(int) is relatively high due to the relatively poor quality of the
crystal resulting in the weak intensities of some high-angle reflections.
An appropiate structural model could only be obtained the current
space group.
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2548
_diffrn_reflns_av_R_equivalents  0.1459
_diffrn_reflns_av_sigmaI/netI    0.0724
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.08
_reflns_number_total             2548
_reflns_number_gt                1182
_reflns_threshold_expression     I>2\s

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'DIAMOND (Brandenburg, 2006)'

_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. Two of the carbon atoms in
the pheny ring are disorded. SADI and EADP restraints
were applied to C2, C2', C3 and C3'.
;

_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^)+(0.1990P)^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         2548
_refine_ls_number_parameters     126
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1417
_refine_ls_R_factor_gt           0.0924
_refine_ls_wR_factor_ref         0.3261
_refine_ls_wR_factor_gt          0.2989
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.6758(5) 0.9299(6) 0.2157(2) 0.102(3) Uani 1 1 d . . .
C2 C 0.5999(11) 0.9287(17) 0.2212(5) 0.125(8) Uani 0.60 1 d PD A 1
H2 H 0.5822 0.9255 0.2399 0.150 Uiso 0.60 1 calc PR A 1
C3 C 0.5424(11) 0.9322(9) 0.1989(5) 0.099(3) Uani 0.60 1 d PD A 1
H3 H 0.4936 0.9400 0.2025 0.119 Uiso 0.60 1 calc PR A 1
C2' C 0.5740(19) 0.885(3) 0.2240(7) 0.125(8) Uani 0.40 1 d PD A 2
H2' H 0.5499 0.8629 0.2418 0.150 Uiso 0.40 1 calc PR A 2
C3' C 0.5237(19) 0.8838(15) 0.1989(7) 0.099(3) Uani 0.40 1 d PD A 2
H3' H 0.4615 0.8563 0.1998 0.119 Uiso 0.40 1 calc PR A 2
C4 C 0.5670(7) 0.9231(7) 0.1736(2) 0.106(3) Uani 1 1 d . . .
H4 H 0.5265 0.9082 0.1588 0.127 Uiso 1 1 calc R A 1
C5 C 0.6464(5) 0.9342(5) 0.16844(18) 0.087(2) Uani 1 1 d . A .
H5 H 0.6644 0.9388 0.1497 0.104 Uiso 1 1 calc R . .
C6 C 0.7050(5) 0.9394(5) 0.18917(18) 0.079(2) Uani 1 1 d . A .
C7 C 0.8186(5) 0.9610(5) 0.15680(16) 0.084(2) Uani 1 1 d . A .
H7A H 0.8137 1.0077 0.1469 0.101 Uiso 1 1 calc R . .
H7B H 0.7827 0.9052 0.1467 0.101 Uiso 1 1 calc R . .
C8 C 0.9131(5) 0.9830(5) 0.15680(14) 0.0730(19) Uani 1 1 d . . .
C9 C 0.9328(5) 0.9112(5) 0.15583(16) 0.080(2) Uani 1 1 d . . .
C10 C 0.8577(5) 0.8193(5) 0.15820(18) 0.091(2) Uani 1 1 d . . .
H10A H 0.8762 0.7845 0.1695 0.110 Uiso 1 1 calc R . .
H10B H 0.8087 0.8202 0.1680 0.110 Uiso 1 1 calc R . .
C11 C 0.8270(8) 0.7772(9) 0.1322(3) 0.164(5) Uani 1 1 d . . .
H11A H 0.7760 0.7186 0.1350 0.246 Uiso 1 1 calc R . .
H11B H 0.8738 0.7717 0.1230 0.246 Uiso 1 1 calc R . .
H11C H 0.8102 0.8121 0.1206 0.246 Uiso 1 1 calc R . .
N1 N 0.7852(4) 0.9526(4) 0.18383(13) 0.0835(18) Uani 1 1 d . . .
H1 H 0.8188 0.9562 0.1978 0.100 Uiso 1 1 calc R A .
S2 S 0.74430(18) 0.9360(2) 0.24422(5) 0.1215(10) Uani 1 1 d . . .
I1 I 0.0000 0.0000 0.22287(2) 0.1141(7) Uani 1 3 d S . .

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 0.083(6) 0.129(7) 0.118(8) 0.007(6) -0.022(5) 0.071(5)
C2 0.079(12) 0.18(3) 0.115(9) 0.094(13) 0.062(9) 0.063(14)
C3 0.066(8) 0.075 0.152(10) -0.005(13) -0.016(8) 0.032(9)
C2' 0.079(12) 0.18(3) 0.115(9) 0.094(13) 0.062(9) 0.063(14)
C3' 0.066(8) 0.075 0.152(10) -0.005(13) -0.016(8) 0.032(9)
C4 0.104(7) 0.132(8) 0.091(7) -0.002(5) 0.003(5) 0.066(6)
C5 0.069(5) 0.097(6) 0.101(6) 0.001(5) -0.011(4) 0.048(4)
C6 0.072(5) 0.071(4) 0.090(6) 0.000(4) 0.008(4) 0.032(4)
C7 0.083(5) 0.094(5) 0.082(6) -0.020(4) -0.023(4) 0.048(4)
C8 0.080(5) 0.079(5) 0.057(4) 0.000(3) 0.006(3) 0.037(4)
C9 0.080(5) 0.072(5) 0.088(5) -0.001(4) 0.014(4) 0.039(4)
C10 0.089(6) 0.080(5) 0.100(6) -0.015(5) 0.007(5) 0.039(5)
C11 0.138(10) 0.139(9) 0.144(11) -0.009(8) 0.017(8) 0.016(8)
N1 0.072(4) 0.109(5) 0.076(4) -0.004(3) -0.013(3) 0.050(4)
S2 0.125(2) 0.186(3) 0.0992(18) 0.0260(17) 0.0140(15) 0.1123(19)
I1 0.1297(9) 0.1297(9) 0.0829(9) 0.000 0.000 0.0649(4)

_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 1.35(2) . ?
C1 C6 1.360(12) . ?
C1 C2' 1.60(3) . ?
C1 S2 1.798(8) . ?
C2 C3 1.498(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.33(2) . ?
C3 H3 0.9500 . ?
C2' C3' 1.499(16) . ?
C2' H2' 0.9500 . ?
C3' C4 1.42(3) . ?
C3' H3' 0.9500 . ?
C4 C5 1.334(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(11) . ?
C5 H5 0.9500 . ?
C6 N1 1.334(9) . ?
C7 N1 1.410(10) . ?
C7 C8 1.507(10) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.345(10) 3_675 ?
C8 C9 1.467(10) . ?
C9 C8 1.346(10) 2_765 ?
C9 C10 1.495(10) . ?
C10 C11 1.421(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N1 H1 0.8800 . ?
S2 S2 2.027(7) 5_675 ?
I1 I1 2.623(2) 4 ?

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 119.7(11) . . ?
C6 C1 C2' 123.8(14) . . ?
C2 C1 S2 118.5(12) . . ?
C6 C1 S2 121.0(6) . . ?
C2' C1 S2 112.7(12) . . ?
C1 C2 C3 122.7(18) . . ?
C1 C2 H2 118.6 . . ?
C3 C2 H2 118.6 . . ?
C4 C3 C2 112.8(17) . . ?
C4 C3 H3 123.6 . . ?
C2 C3 H3 123.6 . . ?
C3' C2' C1 108(2) . . ?
C3' C2' H2' 126.0 . . ?
C1 C2' H2' 126.0 . . ?
C4 C3' C2' 121(2) . . ?
C4 C3' H3' 119.3 . . ?
C2' C3' H3' 119.3 . . ?
C3 C4 C5 122.2(11) . . ?
C5 C4 C3' 119.9(13) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C3' C4 H4 111.7 . . ?
C4 C5 C6 123.7(8) . . ?
C4 C5 H5 118.1 . . ?
C6 C5 H5 118.1 . . ?
N1 C6 C1 120.3(8) . . ?
N1 C6 C5 123.3(8) . . ?
C1 C6 C5 116.4(7) . . ?
N1 C7 C8 112.0(6) . . ?
N1 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C9 120.4(8) 3_675 . ?
C9 C8 C7 120.5(7) 3_675 . ?
C9 C8 C7 118.9(7) . . ?
C8 C9 C8 119.3(8) 2_765 . ?
C8 C9 C10 122.2(7) 2_765 . ?
C8 C9 C10 117.8(7) . . ?
C11 C10 C9 113.3(8) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
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 . . ?
C6 N1 C7 123.1(6) . . ?
C6 N1 H1 118.5 . . ?
C7 N1 H1 118.5 . . ?
C1 S2 S2 105.2(3) . 5_675 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.631
_refine_diff_density_min         -1.092
_refine_diff_density_rms         0.130
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0