#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/85/7218527.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7218527
loop_
_publ_author_name
'Koskinen, L.'
'Hirva, P.'
'Kalenius, E.'
'Jääskeläinen, S.'
'Rissanen, K.'
'Haukka, M.'
_publ_section_title
;
 Halogen bonds with coordinative nature: halogen bonding in a S--I+--S
 iodonium complex
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              1231
_journal_paper_doi               10.1039/C4CE01735H
_journal_volume                  17
_journal_year                    2015
_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
_chemical_melting_point          119.5(5)
_chemical_name_common            '[I(etu)2]+  I-  [I3]- '
_chemical_name_systematic        '[I(2-imidazolidinethione)2]+  I-  [I3]- '
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4457(4)
_cell_length_b                   14.5288(3)
_cell_length_c                   13.7814(3)
_cell_measurement_reflns_used    9798
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.43
_cell_measurement_theta_min      2.48
_cell_volume                     2892.42(12)
_computing_cell_refinement       'SAINT (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT (Bruker AXS, 2009)'
_computing_molecular_graphics
'CrystaMaker (CrystalMaker Software ltd., 2011)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '62mm x 62mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Bruker KAPPA APEX II DUO CCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  'curved graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            47977
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.453
_diffrn_reflns_theta_min         2.477
_exptl_absorpt_coefficient_mu    6.751
_exptl_absorpt_correction_T_max  0.5292
_exptl_absorpt_correction_T_min  0.1835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            'orange red'
_exptl_crystal_density_diffrn    2.687
_exptl_crystal_description       plate
_exptl_crystal_F_000             2136
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.319
_exptl_crystal_size_min          0.108
_refine_diff_density_max         1.447
_refine_diff_density_min         -1.187
_refine_diff_density_rms         0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         7055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0203
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0091P)²+4.5475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0394
_refine_ls_wR_factor_ref         0.0429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6098
_reflns_number_total             7055
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ce01735h2.cif
_cod_data_source_block           lk201010_2_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '119-120' was changed to '119.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 7218527.cif.
;
_cod_database_code               7218527
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelx_estimated_absorpt_t_min   0.184
_shelx_estimated_absorpt_t_max   0.529
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
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'
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
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
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'
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_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_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_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_publ_flag
N2 H2 I1 0.83(3) 2.91(3) 3.4360(16) 123(2) yes
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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199383
