#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/63/2206302.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_2206302
loop_
_publ_author_name
'Santos, Isabel C.'
'Belo, Dulce'
'Mendonça, Joana'
'Figueira, Mauro João'
'Almeida, Manuel'
'Rovira, Concepcion'
_publ_section_title
;
 5,6-Dihydrothieno[2,3-d][1,3]dithiol-2-one
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2161
_journal_page_last               o2163
_journal_paper_doi               10.1107/S1600536805018234
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C5 H4 O S3'
_chemical_formula_moiety         'C5 H4 O S3'
_chemical_formula_sum            'C5 H4 O S3'
_chemical_formula_weight         176.26
_chemical_name_systematic
;
5,6-dihydrothieno[2,3-d][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                 94.651(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.0743(7)
_cell_length_b                   11.154(2)
_cell_length_c                   14.778(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      8
_cell_volume                     669.4(2)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection
'CAD-4 Software (Enraf--Nonius, 1989 or 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω--2θ
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1476
_diffrn_reflns_theta_full        26.98
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         3.65
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  3600
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    1.009
_exptl_absorpt_correction_T_max  0.9491
_exptl_absorpt_correction_T_min  0.8253
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.346
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0384P)²+1.0429P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                1132
_reflns_number_total             1423
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6203.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206302
_cod_database_fobs_code          2206302
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_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
_atom_site_type_symbol
C1 0.8992(8) 0.3713(3) 0.2422(2) 0.0309(7) Uani d . 1 C
S1 0.8260(2) 0.45795(7) 0.33978(5) 0.0302(2) Uani d . 1 S
S2 0.7734(2) 0.21974(7) 0.25081(5) 0.0328(2) Uani d . 1 S
S3 0.5720(2) 0.34529(8) 0.51140(6) 0.0394(3) Uani d . 1 S
C2 0.6687(7) 0.3399(3) 0.39890(19) 0.0244(6) Uani d . 1 C
C3 0.6432(7) 0.2321(3) 0.3594(2) 0.0248(6) Uani d . 1 C
C4 0.5310(7) 0.1270(3) 0.41925(19) 0.0238(6) Uani d . 1 C
H4A 0.3476 0.0836 0.3888 0.029 Uiso calc R 1 H
H4B 0.7103 0.0716 0.4347 0.029 Uiso calc R 1 H
C5 0.4267(9) 0.1926(3) 0.5043(2) 0.0382(8) Uani d . 1 C
H5A 0.5125 0.1494 0.5581 0.046 Uiso calc R 1 H
H5B 0.1883 0.1923 0.5032 0.046 Uiso calc R 1 H
O 1.0221(7) 0.4119(2) 0.17777(16) 0.0450(6) Uani d . 1 O
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
C1 0.0349(17) 0.0320(16) 0.0269(15) 0.0042(14) 0.0089(13) 0.0018(13)
S1 0.0405(5) 0.0227(4) 0.0291(4) -0.0030(3) 0.0120(3) 0.0009(3)
S2 0.0451(5) 0.0297(4) 0.0246(4) -0.0001(4) 0.0091(3) -0.0053(3)
S3 0.0546(6) 0.0344(5) 0.0311(4) -0.0036(4) 0.0163(4) -0.0032(4)
C2 0.0292(16) 0.0237(14) 0.0208(13) -0.0012(12) 0.0053(11) 0.0018(11)
C3 0.0261(15) 0.0257(14) 0.0226(13) -0.0014(12) 0.0025(11) -0.0013(12)
C4 0.0282(15) 0.0215(13) 0.0225(14) -0.0043(12) 0.0061(12) -0.0026(11)
C5 0.042(2) 0.0388(19) 0.0345(18) -0.0058(16) 0.0098(15) 0.0067(15)
O 0.0592(16) 0.0458(14) 0.0329(13) 0.0016(13) 0.0223(12) 0.0075(11)
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
O C1 S2 123.9(3)
O C1 S1 123.1(3)
S2 C1 S1 113.04(17)
C2 S1 C1 95.08(15)
C3 S2 C1 95.85(14)
C2 S3 C5 90.60(15)
C3 C2 S1 118.9(2)
C3 C2 S3 115.6(2)
S1 C2 S3 125.26(18)
C2 C3 C4 116.4(3)
C2 C3 S2 117.1(2)
C4 C3 S2 126.2(2)
C5 C4 C3 102.6(2)
C5 C4 H4A 111.2
C3 C4 H4A 111.2
C5 C4 H4B 111.2
C3 C4 H4B 111.2
H4A C4 H4B 109.2
C4 C5 S3 112.6(2)
C4 C5 H5A 109.1
S3 C5 H5A 109.1
C4 C5 H5B 109.1
S3 C5 H5B 109.1
H5A C5 H5B 107.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O 1.201(4) yes
C1 S2 1.774(3) yes
C1 S1 1.781(3) yes
S1 C2 1.732(3) yes
S2 C3 1.737(3) yes
S3 C2 1.740(3) yes
S3 C5 1.804(4) yes
C2 C3 1.337(4) yes
C3 C4 1.559(4) yes
C4 C5 1.543(4) yes
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 S3 3.5860(10) 1_555 3_666 yes
S3 S1 3.5860(10) 1_555 3_666 ?
S3 S3 3.5120(10) 1_555 3_666 yes
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 O 2_645 0.97 2.58 3.517(4) 162
C5 H5A O 4_566 0.97 2.70 3.578(5) 150
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9074468
