#------------------------------------------------------------------------------
#$Date: 2018-05-22 18:48:05 +0300 (Tue, 22 May 2018) $
#$Revision: 207905 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/25/2242506.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2242506
loop_
_publ_author_name
'Trentin, Ivan'
'Schindler, Claudia'
'Schulzke, Carola'
_publ_section_title
;
 Crystal structures of
 4,4'-(disulfane-1,2-diyl)bis(5-methyl-2H-1,3-dithiol-2-one) and
 4,4'-(diselanane-1,2-diyl)bis(5-methyl-2H-1,3-dithiol-2-one)
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              840
_journal_page_last               845
_journal_paper_doi               10.1107/S2056989018007454
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C8 H6 O2 S6'
_chemical_formula_moiety         'C8 H6 O2 S6'
_chemical_formula_sum            'C8 H6 O2 S6'
_chemical_formula_weight         326.49
_chemical_name_systematic
;
4,4'-(Diselanane-1,2-diyl)bis(5-methyl-2H-1,3-dithiol-2-one)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 108.95(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.845(2)
_cell_length_b                   9.0387(18)
_cell_length_c                   13.370(3)
_cell_measurement_reflns_used    13753
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      58.5
_cell_measurement_theta_min      6.4
_cell_volume                     1239.6(5)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2010)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2010)
;
_computing_data_reduction
;
X-AREA (Stoe & Cie, 2010)
;
_computing_molecular_graphics
;
XP (Bruker, 1998), DIAMOND (Brandenburg, 2001),
Mercury (Macrae et al.,  2006)
;
_computing_publication_material
;
CIFTAB (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2016/6 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR-92 (Altomare et al.,  1994), SHELXS2016/6 (Sheldrick,
2008)
;
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       ω
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13324
_diffrn_reflns_theta_full        29.23
_diffrn_reflns_theta_max         29.23
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    1.082
_exptl_absorpt_correction_T_max  0.9421
_exptl_absorpt_correction_T_min  0.7709
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'face indexed'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.344
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         3344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0269
_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)+(0.0310P)²+0.2272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0597
_refine_ls_wR_factor_ref         0.0635
_reflns_number_gt                2636
_reflns_number_total             3344
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            wm5446sup1.cif
_cod_data_source_block           it14ii
_cod_original_cell_volume        1239.6(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2242506
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_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_occupancy
C C1 0.56140(18) 0.97691(18) 0.25987(13) 0.0303(3) Uani d 1
C C2 0.68624(16) 0.94540(18) 0.46161(11) 0.0264(3) Uani d 1
C C3 0.58060(16) 0.85986(19) 0.44516(12) 0.0283(3) Uani d 1
C C4 0.54816(19) 0.7632(2) 0.52398(15) 0.0377(4) Uani d 1
H H4A 0.616846 0.771796 0.592700 0.057 Uiso calc 1
H H4B 0.541661 0.660179 0.500052 0.057 Uiso calc 1
H H4C 0.464737 0.794436 0.530838 0.057 Uiso calc 1
C C5 0.8123(2) 0.6221(2) 0.36279(14) 0.0432(4) Uani d 1
H H5A 0.856072 0.716664 0.361746 0.065 Uiso calc 1
H H5B 0.718458 0.633249 0.326446 0.065 Uiso calc 1
H H5C 0.847281 0.546622 0.326768 0.065 Uiso calc 1
C C6 0.83515(16) 0.5762(2) 0.47454(13) 0.0310(3) Uani d 1
C C7 0.89133(16) 0.6551(2) 0.56261(13) 0.0298(3) Uani d 1
C C8 0.82334(18) 0.4069(2) 0.63253(14) 0.0345(4) Uani d 1
O O1 0.52663(15) 1.00821(15) 0.16765(9) 0.0419(3) Uani d 1
O O2 0.80246(16) 0.30792(16) 0.68404(11) 0.0476(3) Uani d 1
S S1 0.47149(4) 0.85968(5) 0.31651(4) 0.03579(11) Uani d 1
S S2 0.70545(4) 1.04272(5) 0.35471(3) 0.02809(9) Uani d 1
S S3 0.80927(5) 0.96538(5) 0.58353(3) 0.03365(10) Uani d 1
S S4 0.95479(4) 0.83296(5) 0.56233(4) 0.03649(11) Uani d 1
S S5 0.89988(5) 0.57621(5) 0.68428(3) 0.03564(11) Uani d 1
S S6 0.78190(5) 0.40033(5) 0.49318(3) 0.03672(11) Uani d 1
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
O1 C1 S2 124.61(15)
O1 C1 S1 123.25(15)
S2 C1 S1 112.13(9)
C3 C2 S2 118.62(12)
C3 C2 S3 124.44(12)
S2 C2 S3 116.93(10)
C2 C3 C4 127.26(16)
C2 C3 S1 115.65(12)
C4 C3 S1 117.07(13)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C6 C5 H5A 109.5
C6 C5 H5B 109.5
H5A C5 H5B 109.5
C6 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C7 C6 C5 127.68(18)
C7 C6 S6 115.98(13)
C5 C6 S6 116.34(14)
C6 C7 S4 123.61(14)
C6 C7 S5 118.09(14)
S4 C7 S5 118.30(10)
O2 C8 S6 123.42(15)
O2 C8 S5 125.06(15)
S6 C8 S5 111.52(10)
C3 S1 C1 97.47(8)
C2 S2 C1 96.03(8)
C2 S3 S4 101.38(6)
C7 S4 S3 102.29(6)
C7 S5 C8 96.44(8)
C6 S6 C8 97.92(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.200(2)
C1 S2 1.7652(19)
C1 S1 1.7682(19)
C2 C3 1.340(2)
C2 S2 1.7473(16)
C2 S3 1.7486(17)
C3 C4 1.496(2)
C3 S1 1.7426(18)
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 C6 1.492(2)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 C7 1.342(2)
C6 S6 1.7363(19)
C7 S4 1.7494(18)
C7 S5 1.7507(17)
C8 O2 1.195(2)
C8 S6 1.7700(18)
C8 S5 1.7710(19)
S3 S4 2.0723(7)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C4 H4A S3 . 0.98 2.76 3.244(2) 111.4
C5 H5A S4 . 0.98 2.75 3.234(2) 110.9
C4 H4B O1 2_645 0.98 2.53 3.345(2) 140.9
C5 H5C S3 4_575 0.98 3.14 3.8063(19) 126.2
C5 H5C S5 3_766 0.98 3.01 3.825(2) 141.9
C4 H4C S2 3_676 0.98 3.12 4.021(2) 153.1

_cod_database_fobs_code 2242506
