#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/27/2232707.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_2232707
loop_
_publ_author_name
'Kannan, M.'
'Ramkumar, V.'
'Dhamodharan, R.'
_publ_section_title
;
 3-({[(1-Phenylethyl)sulfanyl]methanethioyl}sulfanyl)propanoic acid
;
_journal_coeditor_code           HB6480
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3352
_journal_paper_doi               10.1107/S1600536811046873
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H14 O2 S3'
_chemical_formula_moiety         'C12 H14 O2 S3'
_chemical_formula_sum            'C12 H14 O2 S3'
_chemical_formula_weight         286.41
_chemical_name_systematic
;
3-({[(1-Phenylethyl)sulfanyl]methanethioyl}sulfanyl)propanoic acid
;
_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                 113.039(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6280(8)
_cell_length_b                   10.2908(5)
_cell_length_c                   10.7299(5)
_cell_measurement_reflns_used    4284
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      2.56
_cell_volume                     1384.77(13)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.862
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9109
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.49
_diffrn_reflns_theta_min         2.56
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  0.8938
_exptl_absorpt_correction_T_min  0.8105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.265
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         3020
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0359
_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)+(0.0372P)²+0.5628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0948
_reflns_number_gt                2224
_reflns_number_total             3020
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6480.cif
_cod_data_source_block           I
_cod_original_cell_volume        1384.77(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232707
_cod_database_fobs_code          2232707
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.34830(19) 0.5248(2) 0.1937(3) 0.0664(6) Uani d . 1 1
H H1 0.3225 0.5785 0.1180 0.080 Uiso calc R 1 1
C C2 0.4227(2) 0.4306(3) 0.2022(4) 0.0874(9) Uani d . 1 1
H H2 0.4469 0.4216 0.1328 0.105 Uiso calc R 1 1
C C3 0.4606(2) 0.3509(3) 0.3116(4) 0.0948(11) Uani d . 1 1
H H3 0.5103 0.2870 0.3168 0.114 Uiso calc R 1 1
C C4 0.4260(2) 0.3645(3) 0.4129(4) 0.0912(10) Uani d . 1 1
H H4 0.4519 0.3095 0.4875 0.109 Uiso calc R 1 1
C C5 0.3523(2) 0.4598(2) 0.4070(3) 0.0684(6) Uani d . 1 1
H H5 0.3302 0.4692 0.4783 0.082 Uiso calc R 1 1
C C6 0.31156(16) 0.54066(18) 0.2959(2) 0.0492(5) Uani d . 1 1
C C7 0.23156(16) 0.64611(17) 0.2845(2) 0.0477(5) Uani d . 1 1
H H7 0.1806 0.6504 0.1901 0.057 Uiso calc R 1 1
C C8 0.1697(2) 0.6301(3) 0.3737(3) 0.0832(8) Uani d . 1 1
H H8A 0.1330 0.5482 0.3546 0.125 Uiso calc R 1 1
H H8B 0.1187 0.6993 0.3559 0.125 Uiso calc R 1 1
H H8C 0.2180 0.6327 0.4671 0.125 Uiso calc R 1 1
C C9 0.21603(15) 0.91964(17) 0.24871(19) 0.0421(4) Uani d . 1 1
C C10 0.18484(18) 1.18835(19) 0.2244(2) 0.0553(5) Uani d . 1 1
H H10A 0.1186 1.1527 0.2231 0.066 Uiso calc R 1 1
H H10B 0.2046 1.2608 0.2872 0.066 Uiso calc R 1 1
C C11 0.16642(16) 1.23796(18) 0.0855(2) 0.0479(5) Uani d . 1 1
H H11A 0.2342 1.2624 0.0825 0.057 Uiso calc R 1 1
H H11B 0.1359 1.1692 0.0199 0.057 Uiso calc R 1 1
C C12 0.09317(15) 1.35291(18) 0.0482(2) 0.0444(4) Uani d . 1 1
O O1 0.04244(14) 1.38506(15) 0.11389(17) 0.0706(5) Uani d . 1 1
O O2 0.08929(15) 1.41368(17) -0.05809(18) 0.0708(5) Uani d . 1 1
S S1 0.30835(4) 0.79721(5) 0.32472(6) 0.05737(18) Uani d . 1 1
S S2 0.09018(4) 0.90297(6) 0.15929(6) 0.06006(18) Uani d . 1 1
S S3 0.28670(5) 1.06576(5) 0.28523(7) 0.06266(19) Uani d . 1 1
H H1O 0.051(3) 1.477(3) -0.073(3) 0.111(12) Uiso d . 1 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'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 121.0(3)
C2 C1 H1 119.5
C6 C1 H1 119.5
C3 C2 C1 120.2(3)
C3 C2 H2 119.9
C1 C2 H2 119.9
C4 C3 C2 119.9(3)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 120.8(3)
C3 C4 H4 119.6
C5 C4 H4 119.6
C6 C5 C4 120.3(3)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C1 117.8(2)
C5 C6 C7 122.5(2)
C1 C6 C7 119.66(19)
C6 C7 C8 115.77(18)
C6 C7 S1 105.29(13)
C8 C7 S1 110.65(16)
C6 C7 H7 108.3
C8 C7 H7 108.3
S1 C7 H7 108.3
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
S2 C9 S1 127.34(11)
S2 C9 S3 126.14(11)
S1 C9 S3 106.51(11)
C11 C10 S3 113.87(14)
C11 C10 H10A 108.8
S3 C10 H10A 108.8
C11 C10 H10B 108.8
S3 C10 H10B 108.8
H10A C10 H10B 107.7
C12 C11 C10 111.69(16)
C12 C11 H11A 109.3
C10 C11 H11A 109.3
C12 C11 H11B 109.3
C10 C11 H11B 109.3
H11A C11 H11B 107.9
O1 C12 O2 123.36(18)
O1 C12 C11 122.18(17)
O2 C12 C11 114.46(16)
C12 O2 H1O 112(2)
C9 S1 C7 105.23(9)
C9 S3 C10 104.07(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.380(3)
C1 C6 1.383(3)
C1 H1 0.9300
C2 C3 1.357(5)
C2 H2 0.9300
C3 C4 1.351(5)
C3 H3 0.9300
C4 C5 1.388(4)
C4 H4 0.9300
C5 C6 1.380(3)
C5 H5 0.9300
C6 C7 1.509(3)
C7 C8 1.512(3)
C7 S1 1.8291(19)
C7 H7 0.9800
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 S2 1.614(2)
C9 S1 1.7415(19)
C9 S3 1.7455(19)
C10 C11 1.500(3)
C10 S3 1.799(2)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.498(2)
C11 H11A 0.9700
C11 H11B 0.9700
C12 O1 1.211(2)
C12 O2 1.283(2)
O2 H1O 0.81(3)
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
O2 H1O O1 3_585 0.81(3) 1.85(3) 2.651(2) 177(3)
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
C6 C1 C2 C3 0.4(4)
C1 C2 C3 C4 -0.5(4)
C2 C3 C4 C5 -0.3(4)
C3 C4 C5 C6 1.2(4)
C4 C5 C6 C1 -1.3(3)
C4 C5 C6 C7 -179.8(2)
C2 C1 C6 C5 0.5(3)
C2 C1 C6 C7 179.0(2)
C5 C6 C7 C8 -20.6(3)
C1 C6 C7 C8 160.9(2)
C5 C6 C7 S1 101.9(2)
C1 C6 C7 S1 -76.6(2)
S3 C10 C11 C12 -171.50(14)
C10 C11 C12 O1 -11.6(3)
C10 C11 C12 O2 168.19(19)
S2 C9 S1 C7 -1.18(16)
S3 C9 S1 C7 179.94(9)
C6 C7 S1 C9 156.85(14)
C8 C7 S1 C9 -77.38(19)
S2 C9 S3 C10 8.69(16)
S1 C9 S3 C10 -172.41(10)
C11 C10 S3 C9 -97.04(17)
