#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:50:37 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179992 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/86/7028678.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_7028678
loop_
_publ_author_name
'Biesiada, M.'
'Kourkoumelis, N.'
'Kubicki, M.'
'Owczarzak, A. M.'
'Balas, V.'
'Hadjikakou, S. K.'
_publ_section_title
;
 Fundamental chemistry of iodine. The reaction of di-iodine towards
 thiourea and its methyl-derivative: formation of aminothiazoles and
 aminothiadiazoles through dicationic disulfides.
;
_journal_issue                   12
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4790
_journal_page_last               4806
_journal_paper_doi               10.1039/c3dt53302f
_journal_volume                  43
_journal_year                    2014
_chemical_formula_moiety         '2(C2 H8 N4 S2), I3, 2(I), Cl'
_chemical_formula_sum            'C4 H16 Cl I5 N8 S4'
_chemical_formula_weight         974.44
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.653(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6516(3)
_cell_length_b                   9.7546(2)
_cell_length_c                   13.8230(5)
_cell_measurement_reflns_used    5739
_cell_measurement_temperature    129.9(2)
_cell_measurement_theta_max      75.4687
_cell_measurement_theta_min      3.3923
_cell_volume                     1225.59(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      129.9(2)
_diffrn_detector_area_resol_mean 10.5357
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0097
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3685
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         75.71
_diffrn_reflns_theta_min         4.91
_exptl_absorpt_coefficient_mu    54.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.743
_refine_diff_density_min         -1.399
_refine_diff_density_rms         0.276
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         3685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0994P)²+2.4648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1378
_reflns_number_gt                3404
_reflns_number_total             3685
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt53302f.txt
_cod_data_source_block           2
_cod_original_cell_volume        1225.59(6)
_cod_original_sg_symbol_H-M      ' P 21/n'
_cod_database_code               7028678
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.16085(5) 0.25926(3) 0.61089(3) 0.01917(15) Uani 1 1 d .
Cl1 Cl 0.5000 0.5000 0.5000 0.0203(4) Uani 1 2 d S
S1 S 0.10191(17) 0.18825(14) 0.21745(11) 0.0229(3) Uani 1 1 d .
N11 N -0.0305(6) -0.0450(5) 0.2183(4) 0.0226(10) Uani 1 1 d .
H11B H -0.0655 -0.1128 0.2424 0.027 Uiso 1 1 calc R
H11A H -0.0382 -0.0437 0.1545 0.027 Uiso 1 1 calc R
C1 C 0.0344(7) 0.0561(6) 0.2785(4) 0.0198(11) Uani 1 1 d .
I2 I 0.5000 0.0000 0.5000 0.02527(17) Uani 1 2 d S
S2 S 0.22286(16) 0.30603(14) 0.33811(11) 0.0234(3) Uani 1 1 d .
N12 N 0.0492(7) 0.0594(5) 0.3758(4) 0.0268(11) Uani 1 1 d .
H12A H 0.0155 -0.0066 0.4026 0.032 Uiso 1 1 calc R
H12B H 0.0926 0.1277 0.4131 0.032 Uiso 1 1 calc R
C2 C 0.0968(7) 0.4357(6) 0.3446(4) 0.0194(11) Uani 1 1 d .
I3 I 0.29636(4) -0.16236(4) 0.56926(3) 0.02805(15) Uani 1 1 d .
N21 N -0.0448(6) 0.4295(6) 0.2918(4) 0.0283(11) Uani 1 1 d .
H21A H -0.1025 0.4940 0.2971 0.034 Uiso 1 1 calc R
H21B H -0.0796 0.3609 0.2519 0.034 Uiso 1 1 calc R
N22 N 0.1557(6) 0.5367(5) 0.4061(4) 0.0219(10) Uani 1 1 d .
H22A H 0.1017 0.6032 0.4135 0.026 Uiso 1 1 calc R
H22B H 0.2487 0.5370 0.4393 0.026 Uiso 1 1 calc R
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
I1 0.0214(3) 0.0203(2) 0.0157(3) 0.00028(11) 0.00621(19) 0.00184(11)
Cl1 0.0198(10) 0.0293(9) 0.0112(8) -0.0015(8) 0.0044(7) 0.0020(8)
S1 0.0317(7) 0.0223(7) 0.0181(6) -0.0038(5) 0.0127(6) -0.0064(5)
N11 0.033(3) 0.018(2) 0.018(2) -0.0007(18) 0.011(2) -0.005(2)
C1 0.025(3) 0.019(3) 0.017(2) 0.000(2) 0.008(2) 0.004(2)
I2 0.0285(4) 0.0220(3) 0.0227(3) -0.0016(2) 0.0052(2) 0.0045(2)
S2 0.0212(7) 0.0223(7) 0.0266(7) -0.0064(5) 0.0080(5) -0.0009(5)
N12 0.045(3) 0.022(2) 0.016(2) -0.0036(19) 0.013(2) -0.008(2)
C2 0.022(3) 0.020(3) 0.016(2) 0.001(2) 0.005(2) -0.002(2)
I3 0.0330(3) 0.0216(2) 0.0279(2) 0.00037(13) 0.00799(18) 0.00281(13)
N21 0.021(3) 0.027(3) 0.031(3) -0.008(2) 0.001(2) 0.000(2)
N22 0.018(2) 0.021(2) 0.022(2) -0.0034(19) 0.0001(19) -0.0003(18)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C1 S1 S2 102.7(2) .
N12 C1 N11 122.6(6) .
N12 C1 S1 122.7(5) .
N11 C1 S1 114.7(4) .
I3 I2 I3 180.0 3_656
C2 S2 S1 103.2(2) .
N22 C2 N21 122.8(6) .
N22 C2 S2 114.6(5) .
N21 C2 S2 122.6(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.780(6) .
S1 S2 2.038(2) .
N11 C1 1.307(8) .
C1 N12 1.303(7) .
I2 I3 2.9246(4) 3_656
I2 I3 2.9246(4) .
S2 C2 1.778(6) .
C2 N22 1.300(8) .
C2 N21 1.316(8) .
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
N11 H11B I1 0.86 2.87 3.678(5) 156.6 3_556
N11 H11B I3 0.86 3.19 3.587(5) 110.9 4
N11 H11A Cl1 0.86 2.33 3.159(5) 163.5 2_545
N12 H12A I1 0.86 2.96 3.749(5) 152.6 3_556
N12 H12B S2 0.86 2.56 3.075(6) 119.3 .
N12 H12B I1 0.86 2.89 3.629(5) 145.3 .
N21 H21A I1 0.86 2.86 3.646(6) 152.0 3_566
N21 H21B S1 0.86 2.59 3.095(6) 118.8 .
N21 H21B I1 0.86 2.86 3.597(5) 145.1 4_565
N22 H22A I1 0.86 2.79 3.587(5) 155.9 3_566
N22 H22A I3 0.86 3.27 3.673(5) 111.7 1_565
N22 H22B Cl1 0.86 2.31 3.155(5) 166.5 .
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
S2 S1 C1 N12 8.9(6)
S2 S1 C1 N11 -170.7(4)
C1 S1 S2 C2 -94.5(3)
S1 S2 C2 N22 -169.5(4)
S1 S2 C2 N21 10.7(6)
