#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/61/4506192.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_4506192
loop_
_publ_author_name
'Eccles, Kevin S.'
'Morrison, Robin E.'
'Stokes, Stephen P.'
'O’Mahony, Graham E.'
'Hayes, John A.'
'Kelly, Dawn M.'
'O’Boyle, Noel M.'
'Fábián, László'
'Moynihan, Humphrey A.'
'Maguire, Anita R.'
'Lawrence, Simon E.'
_publ_section_title
;
 Utilizing Sulfoxide···Iodine Halogen Bonding for
 Cocrystallization
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2969
_journal_paper_doi               10.1021/cg300189v
_journal_volume                  12
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H8 O S2'
_chemical_formula_sum            'C12 H8 O S2'
_chemical_formula_weight         232.30
_chemical_melting_point          414.0(10)
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.011(3)
_cell_length_b                   32.093(6)
_cell_length_c                   4.0823(8)
_cell_measurement_reflns_used    1163
_cell_measurement_temperature    293.(2)
_cell_measurement_theta_max      25.3736
_cell_measurement_theta_min      2.8434
_cell_volume                     2097.7(7)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2009, 3, 0, 0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'Mercury 2.3 (Macrae et al, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX II DUO'
_diffrn_measurement_method       'φ & ω  scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2741
_diffrn_reflns_theta_full        25.88
_diffrn_reflns_theta_max         25.88
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.473
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.165
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.25(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         907
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0317P)²+0.4306P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0685
_reflns_number_gt                826
_reflns_number_total             907
_reflns_threshold_expression     >2sigma(I)
_iucr_refine_instructions_details
;
TITL Kevin in Fdd2
CELL 0.71073  16.0110  32.0930   4.0823  90.000  90.000  90.000
ZERR    8.00   0.0032   0.0064   0.0008   0.000   0.000   0.000
LATT -4
SYMM -X, -Y, Z
SYMM 0.25+X, 0.25-Y, 0.25+Z
SYMM 0.25-X, 0.25+Y, 0.25+Z
SFAC C  H  O  S
UNIT 96  64  8  16
L.S. 5
ACTA
BOND $H
FMAP 2
PLAN 5
WGHT    0.030300
FVAR       0.11151
MOLE 1
S1    4    1.078388    0.029600    0.312107    11.00000    0.07742    0.05158 =
         0.07042    0.01993    0.02887    0.01466
O2    3    1.141067    0.053828    0.391481    10.50000    0.04754    0.04764 =
         0.14040    0.01554    0.01286   -0.01856
C3    1    0.983698    0.046639    0.495757    11.00000    0.05418    0.04102 =
         0.04012    0.00566   -0.00305    0.01054
C4    1    0.977754    0.086160    0.627145    11.00000    0.06011    0.03912 =
         0.06551    0.00234   -0.01328    0.00389
AFIX  43
H4    2    1.024011    0.103686    0.626338    11.00000   -1.20000
AFIX   0
C5    1    0.903516    0.099645    0.759222    11.00000    0.07118    0.04643 =
         0.07172   -0.01296   -0.01003    0.01717
AFIX  43
H5    2    0.899460    0.126432    0.844668    11.00000   -1.20000
AFIX   0
C6    1    0.835056    0.073579    0.765393    11.00000    0.06154    0.06109 =
         0.06377   -0.00342   -0.00140    0.02392
AFIX  43
H6    2    0.785147    0.082783    0.856757    11.00000   -1.20000
AFIX   0
C7    1    0.840283    0.033684    0.635928    11.00000    0.05373    0.05555 =
         0.05102    0.00770   -0.00685    0.00617
AFIX  43
H7    2    0.794148    0.016090    0.641102    11.00000   -1.20000
AFIX   0
C8    1    0.914613    0.020275    0.499122    11.00000    0.05673    0.04037 =
         0.03763    0.00116   -0.00640    0.00975
HKLF 4
 
REM  Kevin in Fdd2
REM R1 =  0.0298 for    826 Fo > 4sig(Fo)  and  0.0338 for all    907 data
REM     73 parameters refined using      1 restraints
 
END  
     
WGHT      0.0306      0.4827 
REM Highest difference peak  0.149,  deepest hole -0.169,  1-sigma level  0.034
Q1    1   0.9579  0.0304  0.5435  11.00000  0.05    0.15
Q2    1   1.0644  0.1006  0.4933  11.00000  0.05    0.11
Q3    1   1.1798  0.0548  0.7294  11.00000  0.05    0.09
Q4    1   0.6915  0.0210  0.5402  11.00000  0.05    0.09
Q5    1   1.1854  0.0184  0.3347  11.00000  0.05    0.09

;
_cod_data_source_file            cg300189v_si_002.cif
_cod_data_source_block           f
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '413 - 415' was changed to
'414.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               4506192
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.07839(5) 0.029599(19) 0.31185(15) 0.0665(3) Uani d . 1
C C7 -0.09648(16) 0.09964(8) 0.7589(7) 0.0630(7) Uani d . 1
H H7 -0.1006 0.1264 0.8443 0.076 Uiso calc R 1
C C3 0.08538(14) -0.02029(7) 0.4989(5) 0.0450(5) Uani d . 1
C C4 0.15975(15) -0.03369(7) 0.6357(5) 0.0535(6) Uani d . 1
H H4 0.2059 -0.0161 0.6407 0.064 Uiso calc R 1
C C5 -0.01631(13) 0.04663(6) 0.4955(5) 0.0451(5) Uani d . 1
C C6 -0.02221(15) 0.08618(7) 0.6269(6) 0.0549(6) Uani d . 1
H H6 0.0241 0.1037 0.6262 0.066 Uiso calc R 1
C C8 -0.16496(15) 0.07358(8) 0.7651(7) 0.0621(7) Uani d . 1
H H8 -0.2149 0.0828 0.8566 0.075 Uiso calc R 1
O O2 0.1411(2) 0.05383(10) 0.3915(12) 0.0786(13) Uani d P 0.5
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0774(5) 0.0515(4) 0.0704(4) 0.0147(3) 0.0290(3) 0.0200(3)
C7 0.0714(17) 0.0464(13) 0.0713(19) 0.0173(12) -0.0099(14) -0.0128(14)
C3 0.0568(14) 0.0405(11) 0.0376(11) 0.0096(10) 0.0065(10) -0.0011(9)
C4 0.0537(14) 0.0557(14) 0.0511(16) 0.0064(11) 0.0068(10) -0.0078(11)
C5 0.0542(13) 0.0410(12) 0.0401(11) 0.0106(10) -0.0030(10) 0.0057(10)
C6 0.0603(15) 0.0390(12) 0.0655(15) 0.0042(11) -0.0133(12) 0.0022(11)
C8 0.0616(15) 0.0610(16) 0.0638(16) 0.0239(13) -0.0013(13) -0.0036(14)
O2 0.0474(18) 0.0475(18) 0.141(4) -0.0187(17) 0.013(2) 0.016(2)
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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O2 S1 C3 . . 112.31(19)
O2 S1 C5 . . 111.47(19)
C3 S1 C5 . . 98.59(10)
C6 C7 C8 . . 120.3(2)
C6 C7 H7 . . 119.9
C8 C7 H7 . . 119.9
C4 C3 C5 . 2 119.9(2)
C4 C3 S1 . . 120.50(17)
C5 C3 S1 2 . 119.53(17)
C3 C4 C8 . 2 119.5(2)
C3 C4 H4 . . 120.3
C8 C4 H4 2 . 120.3
C6 C5 C3 . 2 120.0(2)
C6 C5 S1 . . 120.31(18)
C3 C5 S1 2 . 119.67(17)
C7 C6 C5 . . 120.0(2)
C7 C6 H6 . . 120.0
C5 C6 H6 . . 120.0
C7 C8 C4 . 2 120.3(2)
C7 C8 H8 . . 119.8
C4 C8 H8 2 . 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 O2 . 1.311(3)
S1 C3 . 1.777(2)
S1 C5 . 1.778(2)
C7 C6 . 1.375(3)
C7 C8 . 1.379(4)
C7 H7 . 0.93
C3 C4 . 1.384(3)
C3 C5 2 1.392(3)
C4 C8 2 1.388(3)
C4 H4 . 0.93
C5 C6 . 1.381(3)
C5 C3 2 1.392(3)
C6 H6 . 0.93
C8 C4 2 1.388(3)
C8 H8 . 0.93
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 226448
