#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/00/2220080.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_2220080
loop_
_publ_author_name
'Liang, Yao-Ren'
'Tong, Hung-Chun'
'Lo, Yih-Hsing'
'Lin, Chia-Her'
'Kuo, Ting Shen'
_publ_section_title
;
 Methylene bis(dithiobenzoate)
;
_journal_coeditor_code           BI2313
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2366
_journal_paper_doi               10.1107/S1600536808037379
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C15 H12 S4'
_chemical_formula_moiety         'C15 H12 S4'
_chemical_formula_sum            'C15 H12 S4'
_chemical_formula_weight         320.49
_chemical_name_systematic
;
Methylene bis(dithiobenzoate)
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.5800(3)
_cell_length_b                   14.6440(11)
_cell_length_c                   4.2710(7)
_cell_measurement_reflns_used    5256
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.04
_cell_volume                     724.27(13)
_computing_cell_refinement
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       φ
_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  0.0964
_diffrn_reflns_av_sigmaI/netI    0.0876
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5256
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.463
_refine_ls_abs_structure_details 'Flack (1983), 505 Friedel pairs'
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         1317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0733P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1574
_reflns_number_gt                931
_reflns_number_total             1317
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2313.cif
_cod_data_source_block           I
_cod_database_code               2220080
_cod_database_fobs_code          2220080
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
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 0.47264(14) 0.89784(9) 0.5726(3) 0.0446(5) Uani d . 1
S S2 0.72612(15) 0.92562(10) 0.5091(5) 0.0613(6) Uani d . 1
C C1 0.5000 1.0000 0.792(2) 0.049(2) Uani d S 1
H H1A 0.4346 1.0109 0.9253 0.058 Uiso d R 1
C C2 0.6098(5) 0.8635(4) 0.4525(14) 0.0437(15) Uani d . 1
C C3 0.6104(5) 0.7734(4) 0.2900(15) 0.0381(14) Uani d . 1
C C4 0.7071(5) 0.7447(4) 0.1238(15) 0.0480(17) Uani d . 1
H H4A 0.7733 0.7828 0.1147 0.058 Uiso calc R 1
C C5 0.7082(6) 0.6617(4) -0.0279(16) 0.0572(18) Uani d . 1
H H5A 0.7749 0.6428 -0.1397 0.069 Uiso calc R 1
C C6 0.6127(6) 0.6064(4) -0.0173(15) 0.0562(18) Uani d . 1
H H6A 0.6136 0.5491 -0.1211 0.067 Uiso calc R 1
C C7 0.5161(6) 0.6336(4) 0.1422(16) 0.0600(19) Uani d . 1
H H7A 0.4503 0.5949 0.1492 0.072 Uiso calc R 1
C C8 0.5140(6) 0.7159(4) 0.2913(15) 0.0499(17) Uani d . 1
H H8A 0.4459 0.7345 0.3977 0.060 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 0.0456(9) 0.0410(8) 0.0472(9) -0.0042(7) 0.0029(7) 0.0005(7)
S2 0.0472(10) 0.0568(9) 0.0800(14) -0.0132(7) -0.0145(9) 0.0109(10)
C1 0.063(7) 0.043(5) 0.039(5) -0.008(4) 0.000 0.000
C2 0.042(4) 0.048(3) 0.041(3) -0.003(2) -0.012(3) 0.017(3)
C3 0.035(3) 0.035(3) 0.044(4) 0.001(3) 0.000(3) 0.016(3)
C4 0.038(4) 0.058(4) 0.048(4) 0.002(3) 0.002(3) 0.018(3)
C5 0.055(4) 0.062(4) 0.054(4) 0.019(3) 0.016(4) 0.011(4)
C6 0.068(5) 0.039(3) 0.062(4) 0.013(3) 0.012(4) -0.001(4)
C7 0.057(5) 0.046(3) 0.077(5) -0.001(3) 0.017(4) -0.005(3)
C8 0.044(4) 0.042(3) 0.064(4) 0.003(3) 0.008(4) 0.001(3)
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'
Ru Ru -1.2594 0.8363 '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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 S1 C1 . . 103.5(2)
S1 C1 S1 . 2_675 116.9(5)
S1 C1 H1A . . 108.0
S1 C1 H1A 2_675 . 108.0
C3 C2 S2 . . 123.6(4)
C3 C2 S1 . . 113.4(4)
S2 C2 S1 . . 123.0(4)
C4 C3 C8 . . 117.5(6)
C4 C3 C2 . . 120.6(5)
C8 C3 C2 . . 121.8(5)
C5 C4 C3 . . 121.0(6)
C5 C4 H4A . . 119.5
C3 C4 H4A . . 119.5
C6 C5 C4 . . 119.9(6)
C6 C5 H5A . . 120.1
C4 C5 H5A . . 120.1
C7 C6 C5 . . 120.3(6)
C7 C6 H6A . . 119.9
C5 C6 H6A . . 119.9
C8 C7 C6 . . 120.2(7)
C8 C7 H7A . . 119.9
C6 C7 H7A . . 119.9
C7 C8 C3 . . 121.1(6)
C7 C8 H8A . . 119.5
C3 C8 H8A . . 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C2 . 1.743(6)
S1 C1 . 1.794(5)
S2 C2 . 1.643(6)
C1 S1 2_675 1.794(5)
C1 H1A . 0.960
C2 C3 . 1.491(8)
C3 C4 . 1.391(8)
C3 C8 . 1.399(8)
C4 C5 . 1.377(9)
C4 H4A . 0.950
C5 C6 . 1.370(9)
C5 H5A . 0.950
C6 C7 . 1.369(8)
C6 H6A . 0.950
C7 C8 . 1.364(8)
C7 H7A . 0.950
C8 H8A . 0.950
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_site_symmetry_4
_geom_torsion
C2 S1 C1 S1 2_675 78.0(2)
C1 S1 C2 C3 . 174.1(4)
C1 S1 C2 S2 . -6.7(5)
S2 C2 C3 C4 . -12.4(8)
S1 C2 C3 C4 . 166.7(5)
S2 C2 C3 C8 . 169.3(5)
S1 C2 C3 C8 . -11.6(7)
C8 C3 C4 C5 . -1.4(9)
C2 C3 C4 C5 . -179.7(5)
C3 C4 C5 C6 . 0.3(9)
C4 C5 C6 C7 . 0.3(10)
C5 C6 C7 C8 . 0.2(10)
C6 C7 C8 C3 . -1.3(10)
C4 C3 C8 C7 . 1.8(9)
C2 C3 C8 C7 . -179.8(6)
