#------------------------------------------------------------------------------
#$Date: 2016-08-07 11:33:13 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185263 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/53/7225364.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_7225364
loop_
_publ_author_name
'Le Gal, Yann'
'Lorcy, Dominique'
'Jeannin, Olivier'
'Barrière, Frédéric'
'Dorcet, Vincent'
'Lieffrig, Julien'
'Fourmigué, Marc'
_publ_section_title
;
 CS⋯I halogen bonding interactions in crystalline iodinated
 dithiole-2-thiones and thiazole-2-thiones
;
_journal_issue                   29
_journal_name_full               CrystEngComm
_journal_page_first              5474
_journal_paper_doi               10.1039/C6CE00822D
_journal_volume                  18
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C3 H1 I1 S3'
_chemical_formula_sum            'C3 H I S3'
_chemical_formula_weight         260.12
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2016-03-21T14:59:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-05-11 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.224(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.2277(2)
_cell_length_b                   11.0881(8)
_cell_length_c                   14.3608(12)
_cell_measurement_reflns_used    12810
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_measurement_wavelength     0.71073
_cell_volume                     670.40(8)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.130982
_diffrn_orient_matrix_UB_12      -0.06204
_diffrn_orient_matrix_UB_13      0.037329
_diffrn_orient_matrix_UB_21      -0.110674
_diffrn_orient_matrix_UB_22      0.02032
_diffrn_orient_matrix_UB_23      0.058174
_diffrn_orient_matrix_UB_31      -0.166437
_diffrn_orient_matrix_UB_32      -0.062335
_diffrn_orient_matrix_UB_33      -0.018189
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3628
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.675
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.585
_exptl_absorpt_correction_T_max  0.366
_exptl_absorpt_correction_T_min  0.139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    2.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.549
_refine_diff_density_min         -2.943
_refine_diff_density_rms         0.659
_refine_ls_extinction_coef       0.025(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.401
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     65
_refine_ls_number_reflns         1380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.401
_refine_ls_R_factor_all          0.1504
_refine_ls_R_factor_gt           0.0814
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.235
_refine_ls_wR_factor_ref         0.3345
_reflns_Friedel_coverage         0
_reflns_number_gt                998
_reflns_number_total             1380
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce00822d2.cif
_cod_data_source_block           SSI
_cod_depositor_comments
'Adding full bibliography for 7225364--7225367.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7225364
_shelx_res_file
;
 
    shelx.res created by SHELXL-2014/7
 
TITL JL96 in P 21/c
CELL  0.71073   4.2277  11.0881  14.3608   90.000   95.224   90.000
ZERR     4.00   0.0002   0.0008   0.0012    0.000    0.005    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    S    I
UNIT  12   4    12   4
MERG   2
FMAP   2
PLAN   25
conf
acta 50
bond $H
L.S.   8
WGHT    0.200000
EXTI    0.024506
FVAR       0.66295
I1  4    0.840133    0.145774    0.114018    11.00000    0.04452    0.05604 =
         0.04849    0.00352   -0.00212    0.00243
S1    3    0.113714    0.469186   -0.182503    11.00000    0.07926    0.05848 =
         0.05193    0.00041   -0.02204    0.00537
S2    3    0.439737    0.351292   -0.013679    11.00000    0.05993    0.04899 =
         0.04484   -0.00178   -0.00782    0.00089
S3    3    0.404316    0.223730   -0.189304    11.00000    0.06473    0.06429 =
         0.04333   -0.00296   -0.00020    0.00209
C1    1    0.309626    0.353205   -0.130075    11.00000    0.03535    0.05874 =
         0.03741    0.01240   -0.00151    0.00112
C2    1    0.625236    0.213356   -0.014098    11.00000    0.05066    0.06751 =
         0.03490    0.00664    0.00067   -0.00440
C3    1    0.606391    0.152343   -0.094068    11.00000    0.06359    0.04031 =
         0.03612    0.00203    0.01412    0.00794
AFIX  43
H3    2    0.695826    0.076197   -0.098721    11.00000   -1.20000
 
AFIX   0
HKLF    4
 
REM  JL96 in P 21/c
REM R1 =  0.0814 for     998 Fo > 4sig(Fo)  and  0.1504 for all    1380 data
REM     65 parameters refined using      0 restraints
 
END
 
WGHT      0.2000      0.0000
 
REM Highest difference peak  2.549,  deepest hole -2.943,  1-sigma level  0.659
Q1    1   0.8438  0.2113  0.0617  11.00000  0.05    2.55
Q2    1   0.6394  0.1465  0.1224  11.00000  0.05    2.43
Q3    1   0.8387  0.0897  0.0702  11.00000  0.05    2.38
Q4    1   1.0346  0.1494  0.1046  11.00000  0.05    2.33
Q5    1   0.8422  0.2090  0.1614  11.00000  0.05    2.27
Q6    1   0.9163  0.1462  0.0421  11.00000  0.05    2.22
Q7    1   0.6425 -0.0556 -0.1028  11.00000  0.05    2.13
Q8    1   1.1177  0.1322 -0.0202  11.00000  0.05    2.11
Q9    1   0.8888  0.3482  0.0051  11.00000  0.05    1.82
Q10   1   0.1572  0.2421 -0.0128  11.00000  0.05    1.80
Q11   1   1.3244  0.1995  0.1236  11.00000  0.05    1.80
Q12   1   0.2167  0.6511 -0.2173  11.00000  0.05    1.79
Q13   1   0.4848  0.0162 -0.0983  11.00000  0.05    1.78
Q14   1   1.1358  0.0613 -0.0068  11.00000  0.05    1.76
Q15   1   0.5982  0.3445 -0.1757  11.00000  0.05    1.74
Q16   1   0.3826  0.3126 -0.3092  11.00000  0.05    1.73
Q17   1   0.1994  0.4834 -0.0139  11.00000  0.05    1.65
Q18   1   0.5689  0.2229 -0.2493  11.00000  0.05    1.64
Q19   1   1.2554  0.1833  0.1374  11.00000  0.05    1.63
Q20   1   0.8775  0.0194 -0.0107  11.00000  0.05    1.62
Q21   1   1.2173  0.0916  0.0506  11.00000  0.05    1.61
Q22   1  -0.3437  0.4910 -0.1873  11.00000  0.05    1.51
Q23   1   0.5543  0.4803 -0.2597  11.00000  0.05    1.47
Q24   1   0.5348  0.3017  0.1066  11.00000  0.05    1.47
Q25   1   0.4561  0.0860  0.1673  11.00000  0.05    1.47
;
_shelx_res_checksum              58384
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
I1 I 0.8401(2) 0.14577(8) 0.11402(7) 0.0501(7) Uani 1 1 d . .
S1 S 0.1137(10) 0.4692(4) -0.1825(3) 0.0649(13) Uani 1 1 d . .
S2 S 0.4397(10) 0.3513(3) -0.0137(3) 0.0520(11) Uani 1 1 d . .
S3 S 0.4043(9) 0.2237(4) -0.1893(3) 0.0578(11) Uani 1 1 d . .
C1 C 0.310(3) 0.3532(11) -0.1301(11) 0.044(3) Uani 1 1 d . .
C2 C 0.625(3) 0.2134(13) -0.0141(10) 0.051(3) Uani 1 1 d . .
C3 C 0.606(4) 0.1523(10) -0.0941(11) 0.046(3) Uani 1 1 d . .
H3 H 0.6958 0.0762 -0.0987 0.055 Uiso 1 1 calc R U
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 0.0445(9) 0.0560(9) 0.0485(10) 0.0035(3) -0.0021(6) 0.0024(3)
S1 0.079(3) 0.058(2) 0.052(2) 0.0004(16) -0.0220(19) 0.0054(17)
S2 0.060(2) 0.049(2) 0.045(2) -0.0018(12) -0.0078(18) 0.0009(12)
S3 0.065(2) 0.064(2) 0.043(2) -0.0030(14) -0.0002(16) 0.0021(16)
C1 0.035(7) 0.059(8) 0.037(8) 0.012(5) -0.002(6) 0.001(4)
C2 0.051(7) 0.068(9) 0.035(7) 0.007(6) 0.001(6) -0.004(6)
C3 0.064(9) 0.040(6) 0.036(7) 0.002(4) 0.014(7) 0.008(5)
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 0 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-10 1 19 0.216
9 -1 -19 0.246
1 1 19 0.304
-1 -1 -19 0.405
0 1 0 0.011
0 -1 0 0.01
1 -2 -15 0.363
-1 -1 14 0.317
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S3 C3 96.3(7)
C1 S2 C2 96.5(6)
S1 C1 S2 123.5(9)
S1 C1 S3 122.9(9)
S2 C1 S3 113.6(7)
C3 C2 S2 117.7(11)
C3 C2 I1 124.0(11)
S2 C2 I1 118.2(8)
C2 C3 S3 115.8(10)
C2 C3 H3 122.1
S3 C3 H3 122.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C2 2.114(13)
S1 C1 1.671(13)
S2 C1 1.712(15)
S2 C2 1.719(15)
S3 C1 1.734(14)
S3 C3 1.736(15)
C2 C3 1.33(2)
C3 H3 0.93
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
C2 S2 C1 S1 -177.3(9)
C2 S2 C1 S3 2.0(9)
C3 S3 C1 S1 178.1(9)
C3 S3 C1 S2 -1.2(10)
C1 S2 C2 C3 -2.4(13)
C1 S2 C2 I1 -178.1(7)
S2 C2 C3 S3 2.0(17)
I1 C2 C3 S3 177.4(7)
C1 S3 C3 C2 -0.4(14)
