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

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# 
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#  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
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data_lk201010_2_1

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        '[I(2-imidazolidinethione)2]+  I-  [I3]- '
_chemical_name_common            '[I(etu)2]+  I-  [I3]- '
_chemical_melting_point          119-120
_chemical_formula_moiety         'C6 H12 I N4 S2, 0.5(I3), 0.5(I)'
_chemical_formula_sum            'C6 H12 I3 N4 S2'
_chemical_formula_weight         585.02

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.4457(4)
_cell_length_b                   14.5288(3)
_cell_length_c                   13.7814(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2892.42(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9798
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      36.43

_exptl_crystal_description       plate
_exptl_crystal_colour            'orange red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.687
_exptl_crystal_F_000             2136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.319
_exptl_crystal_size_min          0.108
_exptl_absorpt_coefficient_mu    6.751
_shelx_estimated_absorpt_T_min   0.184
_shelx_estimated_absorpt_T_max   0.529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1835
_exptl_absorpt_correction_T_max  0.5292
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_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  'curved graphite crystal'
_diffrn_measurement_device_type  'Bruker KAPPA APEX II DUO CCD'
_diffrn_measurement_device       '62mm x 62mm CCD camera on κ-goniostat'
_diffrn_detector_area_resol_mean 16 # 8 for binned mode
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_reflns_number            47977
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.477
_diffrn_reflns_theta_max         36.453
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7055
_reflns_number_gt                6098
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'CrystaMaker (CrystalMaker Software ltd., 2011)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0091P)²+4.5475P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7055
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0203
_refine_ls_wR_factor_ref         0.0429
_refine_ls_wR_factor_gt          0.0394
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.002
_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_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 0.62952(2) 0.49408(2) -0.25935(2) 0.01204(2) Uani 1 1 d . . . . .
S1 S 0.63633(4) 0.40051(3) -0.09632(3) 0.01601(8) Uani 1 1 d . . . . .
S2 S 0.62606(4) 0.58352(3) -0.42521(3) 0.01526(8) Uani 1 1 d . . . . .
N1 N 0.64464(13) 0.47046(11) 0.08285(12) 0.0172(3) Uani 1 1 d . . . . .
H1 H 0.658(2) 0.418(2) 0.107(2) 0.036(9) Uiso 1 1 d . . . . .
N2 N 0.60663(13) 0.57315(10) -0.02561(12) 0.0172(3) Uani 1 1 d . . . . .
H2 H 0.599(2) 0.596(2) -0.080(2) 0.028(8) Uiso 1 1 d . . . . .
N3 N 0.60958(14) 0.50595(10) -0.60005(12) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.598(2) 0.562(2) -0.622(2) 0.031(8) Uiso 1 1 d . . . . .
N4 N 0.62904(13) 0.40414(10) -0.48570(11) 0.0161(3) Uani 1 1 d . . . . .
H4 H 0.643(2) 0.3823(19) -0.431(2) 0.019(7) Uiso 1 1 d . . . . .
C1 C 0.62883(13) 0.48573(11) -0.01068(12) 0.0128(3) Uani 1 1 d . . . . .
C2 C 0.62542(14) 0.55313(12) 0.14110(13) 0.0166(3) Uani 1 1 d . . . . .
H2A H 0.6767 0.5664 0.1867 0.020 Uiso 1 1 calc R U . . .
H2B H 0.5671 0.5466 0.1781 0.020 Uiso 1 1 calc R U . . .
C3 C 0.61727(15) 0.62832(12) 0.06299(13) 0.0168(3) Uani 1 1 d . . . . .
H3A H 0.5627 0.6681 0.0743 0.020 Uiso 1 1 calc R U . . .
H3B H 0.6737 0.6670 0.0604 0.020 Uiso 1 1 calc R U . . .
C4 C 0.62151(13) 0.49296(11) -0.50561(12) 0.0125(3) Uani 1 1 d . . . . .
C5 C 0.61439(14) 0.41896(12) -0.65426(13) 0.0158(3) Uani 1 1 d . . . . .
H5A H 0.6699 0.4169 -0.6964 0.019 Uiso 1 1 calc R U . . .
H5B H 0.5584 0.4097 -0.6945 0.019 Uiso 1 1 calc R U . . .
C6 C 0.62028(14) 0.34699(11) -0.57277(13) 0.0153(3) Uani 1 1 d . . . . .
H6A H 0.5637 0.3086 -0.5703 0.018 Uiso 1 1 calc R U . . .
H6B H 0.6749 0.3066 -0.5811 0.018 Uiso 1 1 calc R U . . .
I3 I 0.54638(2) 0.76103(2) -0.18799(2) 0.01709(3) Uani 1 1 d . . . . .
I4 I 0.7500 0.7500 -0.18763(2) 0.01656(3) Uani 1 2 d S T P . .
I2 I 0.7500 0.2500 -0.32663(2) 0.01487(3) Uani 1 2 d S T P . .


_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 S1 2.6279(5) . yes
I1 S2 2.6297(5) . yes
S1 C1 1.7139(17) . yes
S2 C4 1.7214(17) . yes
N1 C1 1.328(2) . ?
N1 C2 1.471(2) . ?
N1 H1 0.86(3) . ?
N2 C1 1.326(2) . ?
N2 C3 1.469(2) . ?
N2 H2 0.83(3) . ?
N3 C4 1.326(2) . ?
N3 C5 1.470(2) . ?
N3 H3 0.88(3) . ?
N4 C4 1.324(2) . ?
N4 C6 1.465(2) . ?
N4 H4 0.84(3) . ?
C2 C3 1.538(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.537(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
I3 I4 2.94585(16) . ?
I4 I3 2.94581(16) 2_665 ?

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
S1 I1 S2 178.119(15) . . yes
C1 S1 I1 102.28(6) . . ?
C4 S2 I1 100.52(6) . . ?
C1 N1 C2 111.15(15) . . ?
C1 N1 H1 125(2) . . ?
C2 N1 H1 124(2) . . ?
C1 N2 C3 111.62(15) . . ?
C1 N2 H2 124(2) . . ?
C3 N2 H2 124(2) . . ?
C4 N3 C5 111.73(14) . . ?
C4 N3 H3 120(2) . . ?
C5 N3 H3 128(2) . . ?
C4 N4 C6 112.07(15) . . ?
C4 N4 H4 125.0(19) . . ?
C6 N4 H4 122.6(19) . . ?
N2 C1 N1 110.62(15) . . ?
N2 C1 S1 126.90(14) . . ?
N1 C1 S1 122.47(13) . . ?
N1 C2 C3 102.26(14) . . ?
N1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
N1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
N2 C3 C2 101.67(14) . . ?
N2 C3 H3A 111.4 . . ?
C2 C3 H3A 111.4 . . ?
N2 C3 H3B 111.4 . . ?
C2 C3 H3B 111.4 . . ?
H3A C3 H3B 109.3 . . ?
N4 C4 N3 110.66(15) . . ?
N4 C4 S2 127.48(13) . . ?
N3 C4 S2 121.86(13) . . ?
N3 C5 C6 102.49(14) . . ?
N3 C5 H5A 111.3 . . ?
C6 C5 H5A 111.3 . . ?
N3 C5 H5B 111.3 . . ?
C6 C5 H5B 111.3 . . ?
H5A C5 H5B 109.2 . . ?
N4 C6 C5 102.57(13) . . ?
N4 C6 H6A 111.3 . . ?
C5 C6 H6A 111.3 . . ?
N4 C6 H6B 111.3 . . ?
C5 C6 H6B 111.3 . . ?
H6A C6 H6B 109.2 . . ?
I3 I4 I3 179.809(8) 2_665 . ?

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
C3 N2 C1 N1 6.9(2) . . . . ?
C3 N2 C1 S1 -173.66(15) . . . . ?
C2 N1 C1 N2 4.5(2) . . . . ?
C2 N1 C1 S1 -174.95(14) . . . . ?
I1 S1 C1 N2 11.81(19) . . . . ?
I1 S1 C1 N1 -168.84(15) . . . . ?
C1 N1 C2 C3 -13.0(2) . . . . ?
C1 N2 C3 C2 -14.4(2) . . . . ?
N1 C2 C3 N2 15.4(2) . . . . ?
C6 N4 C4 N3 -1.1(2) . . . . ?
C6 N4 C4 S2 179.11(15) . . . . ?
C5 N3 C4 N4 -3.7(2) . . . . ?
C5 N3 C4 S2 176.13(14) . . . . ?
I1 S2 C4 N4 -6.93(19) . . . . ?
I1 S2 C4 N3 173.27(15) . . . . ?
C4 N3 C5 C6 6.5(2) . . . . ?
C4 N4 C6 C5 5.0(2) . . . . ?
N3 C5 C6 N4 -6.4(2) . . . . ?

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
_geom_hbond_publ_flag
N2 H2 I1 0.83(3) 2.91(3) 3.4360(16) 123(2) . yes

_refine_diff_density_max         1.447
_refine_diff_density_min         -1.187
_refine_diff_density_rms         0.155

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
_database_code_depnum_ccdc_archive 'CCDC 984540'
