#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/10/2211065.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_2211065
loop_
_publ_author_name
'Pu-Zhou Hu'
'Jian-Hua Qin'
'Jun-Qing Chen'
'Lu Wang'
'Bang-Tun Zhao'
_publ_section_title
;
 4,5-Bis(2-hydroxyethylsulfanyl)-1,3-dithiole-2-thione
;
_journal_coeditor_code           HK2152
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5188
_journal_page_last               o5190
_journal_paper_doi               10.1107/S160053680604253X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C7 H10 O2 S5'
_chemical_formula_moiety         'C7 H10 O2 S5'
_chemical_formula_sum            'C7 H10 O2 S5'
_chemical_formula_weight         286.45
_chemical_melting_point          74
_chemical_name_systematic
;
4,5-Bis(2'-hydroxyethylsulfanyl)-1,3-dithiole-2-thione
;
_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                 105.1070(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3016(4)
_cell_length_b                   26.1430(19)
_cell_length_c                   8.7195(6)
_cell_measurement_reflns_used    4756
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.54
_cell_volume                     1166.75(15)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT, (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-2 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7239
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.964
_exptl_absorpt_correction_T_max  0.8857
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.381
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0288
_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)+(0.044P)²+0.1379P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0777
_reflns_number_gt                2383
_reflns_number_total             2668
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2152.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2211065
_cod_database_fobs_code          2211065
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_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 0.47428(9) -0.026909(17) 0.70605(5) 0.05222(14) Uani d . 1
S S2 0.14627(7) 0.032939(14) 0.86669(5) 0.04016(11) Uani d . 1
S S3 0.17256(8) 0.065069(15) 0.55597(5) 0.04475(12) Uani d . 1
S S4 -0.23558(7) 0.116539(17) 0.89809(5) 0.04688(13) Uani d . 1
S S5 -0.19165(8) 0.153892(16) 0.53632(5) 0.04876(13) Uani d . 1
O O1 0.1365(3) 0.19903(4) 1.09771(16) 0.0553(3) Uani d . 1
H H1 0.2506 0.2176 1.1513 0.083 Uiso calc R 1
O O2 0.0233(3) 0.24273(4) 0.78852(15) 0.0541(3) Uani d . 1
H H2 0.0136 0.2280 0.8699 0.081 Uiso calc R 1
C C1 0.2787(3) 0.02142(5) 0.70850(17) 0.0355(3) Uani d . 1
C C2 -0.0362(3) 0.08745(5) 0.79131(18) 0.0353(3) Uani d . 1
C C3 -0.0230(3) 0.10228(5) 0.64601(18) 0.0374(3) Uani d . 1
C C4 -0.0332(3) 0.11428(6) 1.10158(19) 0.0432(3) Uani d . 1
H H4A -0.1371 0.1252 1.1722 0.052 Uiso calc R 1
H H4B 0.0193 0.0791 1.1279 0.052 Uiso calc R 1
C C5 0.2076(3) 0.14708(6) 1.1311(2) 0.0438(3) Uani d . 1
H H5A 0.3070 0.1437 1.2411 0.053 Uiso calc R 1
H H5B 0.3168 0.1358 1.0641 0.053 Uiso calc R 1
C C6 0.0758(4) 0.19894(6) 0.5533(2) 0.0503(4) Uani d . 1
H H6A 0.2080 0.1831 0.5101 0.060 Uiso calc R 1
H H6B 0.0105 0.2287 0.4888 0.060 Uiso calc R 1
C C7 0.2021(3) 0.21635(6) 0.7203(2) 0.0508(4) Uani d . 1
H H7A 0.2705 0.1868 0.7853 0.061 Uiso calc R 1
H H7B 0.3477 0.2387 0.7194 0.061 Uiso calc R 1
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 0.0538(3) 0.0494(2) 0.0527(3) 0.02135(18) 0.0126(2) 0.00228(18)
S2 0.0418(2) 0.03813(19) 0.0437(2) 0.00032(14) 0.01695(16) 0.00318(15)
S3 0.0543(2) 0.0460(2) 0.0339(2) 0.01720(17) 0.01154(17) -0.00046(15)
S4 0.0299(2) 0.0603(3) 0.0520(2) 0.00151(16) 0.01338(16) -0.01432(18)
S5 0.0449(2) 0.0467(2) 0.0457(2) 0.01462(16) -0.00433(17) -0.00369(17)
O1 0.0593(8) 0.0402(6) 0.0601(8) -0.0052(5) 0.0043(6) -0.0048(5)
O2 0.0709(8) 0.0407(6) 0.0468(7) 0.0114(5) 0.0086(6) 0.0014(5)
C1 0.0338(7) 0.0341(7) 0.0368(7) 0.0001(5) 0.0058(6) -0.0029(5)
C2 0.0282(6) 0.0354(7) 0.0421(8) -0.0027(5) 0.0088(5) -0.0082(6)
C3 0.0342(7) 0.0364(7) 0.0388(8) 0.0060(5) 0.0044(6) -0.0065(6)
C4 0.0499(9) 0.0424(8) 0.0425(8) -0.0010(6) 0.0214(7) -0.0012(6)
C5 0.0419(8) 0.0445(8) 0.0424(8) 0.0029(6) 0.0063(6) -0.0049(6)
C6 0.0595(10) 0.0471(8) 0.0469(9) 0.0138(8) 0.0183(8) 0.0103(7)
C7 0.0469(9) 0.0455(8) 0.0569(10) -0.0005(7) 0.0078(8) 0.0042(7)
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
C1 S2 C2 98.14(7)
C1 S3 C3 97.68(7)
C2 S4 C4 102.69(7)
C3 S5 C6 100.23(7)
C5 O1 H1 109.5
C7 O2 H2 109.5
S1 C1 S2 122.32(9)
S1 C1 S3 125.34(9)
S2 C1 S3 112.32(8)
C3 C2 S2 115.42(11)
C3 C2 S4 124.19(12)
S2 C2 S4 120.26(9)
C2 C3 S3 116.42(11)
C2 C3 S5 126.19(12)
S3 C3 S5 117.35(9)
C5 C4 S4 114.04(11)
C5 C4 H4A 108.7
S4 C4 H4A 108.7
C5 C4 H4B 108.7
S4 C4 H4B 108.7
H4A C4 H4B 107.6
O1 C5 C4 110.05(13)
O1 C5 H5A 109.7
C4 C5 H5A 109.7
O1 C5 H5B 109.7
C4 C5 H5B 109.7
H5A C5 H5B 108.2
C7 C6 S5 114.52(12)
C7 C6 H6A 108.6
S5 C6 H6A 108.6
C7 C6 H6B 108.6
S5 C6 H6B 108.6
H6A C6 H6B 107.6
O2 C7 C6 111.98(14)
O2 C7 H7A 109.2
C6 C7 H7A 109.2
O2 C7 H7B 109.2
C6 C7 H7B 109.2
H7A C7 H7B 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.6382(14)
S2 C1 1.7294(15)
S2 C2 1.7513(15)
S3 C1 1.7313(15)
S3 C3 1.7499(14)
S4 C2 1.7538(14)
S4 C4 1.8196(18)
S5 C3 1.7575(15)
S5 C6 1.8193(19)
O1 C5 1.4192(19)
O1 H1 0.8200
O2 C7 1.422(2)
O2 H2 0.8200
C2 C3 1.344(2)
C4 C5 1.503(2)
C4 H4A 0.9700
C4 H4B 0.9700
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.506(3)
C6 H6A 0.9700
C6 H6B 0.9700
C7 H7A 0.9700
C7 H7B 0.9700
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
O1 H1 O2 4_666 0.82 1.92 2.7408(17) 175.8
O2 H2 O1 . 0.82 2.07 2.8444(18) 158.2
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 -179.47(9)
C2 S2 C1 S3 -1.28(9)
C3 S3 C1 S1 179.41(10)
C3 S3 C1 S2 1.29(9)
C1 S2 C2 C3 0.78(13)
C1 S2 C2 S4 176.81(8)
C4 S4 C2 C3 -142.80(13)
C4 S4 C2 S2 41.53(10)
S2 C2 C3 S3 0.02(16)
S4 C2 C3 S3 -175.83(8)
S2 C2 C3 S5 177.71(8)
S4 C2 C3 S5 1.9(2)
C1 S3 C3 C2 -0.81(13)
C1 S3 C3 S5 -178.71(9)
C6 S5 C3 C2 107.30(15)
C6 S5 C3 S3 -75.04(10)
C2 S4 C4 C5 66.63(12)
S4 C4 C5 O1 60.04(16)
C3 S5 C6 C7 -63.27(13)
S5 C6 C7 O2 -61.86(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1737630
