#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/87/2238752.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_2238752
loop_
_publ_author_name
'Abe, Daisuke'
'Sasanuma, Yuji'
_publ_section_title
;
 Butane-1,4-diyl bis(benzenecarbodithioate)
;
_journal_coeditor_code           IS5312
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1636
_journal_paper_doi               10.1107/S1600536813027529
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C18 H18 S4'
_chemical_formula_moiety         'C18 H18 S4'
_chemical_formula_sum            'C18 H18 S4'
_chemical_formula_weight         362.56
_chemical_melting_point          341
_chemical_name_systematic
;
Butane-1,4-diyl bis(benzenecarbodithioate)
;
_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                 110.805(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.0205(6)
_cell_length_b                   7.2535(5)
_cell_length_c                   11.3090(7)
_cell_measurement_reflns_used    5003
_cell_measurement_temperature    173
_cell_measurement_theta_max      67.82
_cell_measurement_theta_min      4.81
_cell_volume                     845.06(9)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;SHELXTL (Sheldrick, 2008) and
 Mercury (Macrae et al., 2006)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4872
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         68.14
_diffrn_reflns_theta_min         4.81
_exptl_absorpt_coefficient_mu    5.091
_exptl_absorpt_correction_T_max  0.9509
_exptl_absorpt_correction_T_min  0.2353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0366
_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)+(0.0393P)²+1.0478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                1468
_reflns_number_total             1480
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is5312.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2238752
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
_atom_site_symmetry_multiplicity
C C1 -0.0082(2) 0.2157(3) 0.3798(2) 0.0226(5) Uani d . 1 1
C C2 0.0225(2) 0.2350(4) 0.5097(2) 0.0271(5) Uani d . 1 1
H H2 0.1068 0.2029 0.5658 0.033 Uiso calc R 1 1
C C3 -0.0686(2) 0.3004(4) 0.5579(2) 0.0309(5) Uani d . 1 1
H H3 -0.0463 0.3138 0.6467 0.037 Uiso calc R 1 1
C C4 -0.1921(2) 0.3461(4) 0.4770(3) 0.0314(6) Uani d . 1 1
H H4 -0.2547 0.3904 0.5100 0.038 Uiso calc R 1 1
C C5 -0.2237(2) 0.3270(4) 0.3480(3) 0.0347(6) Uani d . 1 1
H H5 -0.3085 0.3581 0.2923 0.042 Uiso calc R 1 1
C C6 -0.1329(2) 0.2628(4) 0.2992(2) 0.0300(5) Uani d . 1 1
H H6 -0.1556 0.2508 0.2103 0.036 Uiso calc R 1 1
C C7 0.0885(2) 0.1450(3) 0.3270(2) 0.0222(5) Uani d . 1 1
C C8 0.3424(2) 0.0498(4) 0.3534(2) 0.0288(5) Uani d . 1 1
H H8A 0.3123 -0.0796 0.3375 0.035 Uiso calc R 1 1
H H8B 0.3313 0.1080 0.2710 0.035 Uiso calc R 1 1
C C9 0.4854(2) 0.0543(4) 0.4385(2) 0.0270(5) Uani d . 1 1
H H9A 0.5121 0.1841 0.4594 0.032 Uiso calc R 1 1
H H9B 0.5381 0.0031 0.3913 0.032 Uiso calc R 1 1
S S1 0.04887(5) 0.05242(9) 0.18505(5) 0.0286(2) Uani d . 1 1
S S2 0.24732(5) 0.17228(9) 0.42927(5) 0.0278(2) Uani 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 0.0181 0.0091 '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 0.3331 0.5567 '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 C1 C6 . . 118.6(2)
C2 C1 C7 . . 121.2(2)
C6 C1 C7 . . 120.2(2)
C3 C2 C1 . . 120.7(2)
C3 C2 H2 . . 119.6
C1 C2 H2 . . 119.6
C4 C3 C2 . . 120.1(2)
C4 C3 H3 . . 120.0
C2 C3 H3 . . 120.0
C5 C4 C3 . . 119.6(2)
C5 C4 H4 . . 120.2
C3 C4 H4 . . 120.2
C4 C5 C6 . . 120.5(2)
C4 C5 H5 . . 119.7
C6 C5 H5 . . 119.7
C5 C6 C1 . . 120.4(2)
C5 C6 H6 . . 119.8
C1 C6 H6 . . 119.8
C1 C7 S1 . . 123.48(16)
C1 C7 S2 . . 113.01(16)
S1 C7 S2 . . 123.51(13)
C9 C8 S2 . . 109.43(16)
C9 C8 H8A . . 109.8
S2 C8 H8A . . 109.8
C9 C8 H8B . . 109.8
S2 C8 H8B . . 109.8
H8A C8 H8B . . 108.2
C8 C9 C9 . 3_656 113.5(2)
C8 C9 H9A . . 108.9
C9 C9 H9A 3_656 . 108.9
C8 C9 H9B . . 108.9
C9 C9 H9B 3_656 . 108.9
H9A C9 H9B . . 107.7
C7 S2 C8 . . 104.20(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.392(3)
C1 C6 . 1.395(3)
C1 C7 . 1.487(3)
C2 C3 . 1.386(4)
C2 H2 . 0.9500
C3 C4 . 1.383(4)
C3 H3 . 0.9500
C4 C5 . 1.381(4)
C4 H4 . 0.9500
C5 C6 . 1.384(3)
C5 H5 . 0.9500
C6 H6 . 0.9500
C7 S1 . 1.649(2)
C7 S2 . 1.732(2)
C8 C9 . 1.527(3)
C8 S2 . 1.807(2)
C8 H8A . 0.9900
C8 H8B . 0.9900
C9 C9 3_656 1.530(5)
C9 H9A . 0.9900
C9 H9B . 0.9900
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
C6 C1 C2 C3 . -0.3(4)
C7 C1 C2 C3 . -179.8(2)
C1 C2 C3 C4 . 0.5(4)
C2 C3 C4 C5 . -0.3(4)
C3 C4 C5 C6 . -0.1(4)
C4 C5 C6 C1 . 0.3(4)
C2 C1 C6 C5 . -0.1(4)
C7 C1 C6 C5 . 179.4(2)
C2 C1 C7 S1 . 158.30(19)
C6 C1 C7 S1 . -21.2(3)
C2 C1 C7 S2 . -22.3(3)
C6 C1 C7 S2 . 158.2(2)
S2 C8 C9 C9 3_656 66.7(3)
C1 C7 S2 C8 . 172.54(17)
S1 C7 S2 C8 . -8.11(19)
C9 C8 S2 C7 . -176.88(17)
