#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/87/2238749.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_2238749
loop_
_publ_author_name
'Abe, Daisuke'
'Sasanuma, Yuji'
_publ_section_title
;
 S,S'-Butane-1,4-diyl bis(benzenecarbothioate)
;
_journal_coeditor_code           IS5305
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1612
_journal_paper_doi               10.1107/S1600536813026822
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C18 H18 O2 S2'
_chemical_formula_moiety         'C18 H18 O2 S2'
_chemical_formula_sum            'C18 H18 O2 S2'
_chemical_formula_weight         330.44
_chemical_melting_point          323
_chemical_name_systematic
;
S,S'-Butane-1,4-diyl bis(benzenecarbothioate)
;
_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                 106.8970(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.2230(14)
_cell_length_b                   4.8903(5)
_cell_length_c                   13.2638(15)
_cell_measurement_reflns_used    2016
_cell_measurement_temperature    173
_cell_measurement_theta_max      26.84
_cell_measurement_theta_min      3.15
_cell_volume                     820.67(15)
_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) and PLATON (Spek, 2009)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4326
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_correction_T_min  0.9079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0296
_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)+(0.0413P)²+0.1965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0828
_reflns_number_gt                1626
_reflns_number_total             1845
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is5305.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2238749
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 0.70285(9) 0.4894(3) 0.15671(9) 0.0292(3) Uani d . 1 1
C C2 0.62320(10) 0.6555(3) 0.09507(10) 0.0350(3) Uani d . 1 1
H H2 0.6032 0.6402 0.0205 0.042 Uiso calc R 1 1
C C3 0.57314(11) 0.8429(3) 0.14248(12) 0.0422(3) Uani d . 1 1
H H3 0.5188 0.9562 0.1003 0.051 Uiso calc R 1 1
C C4 0.60192(12) 0.8656(3) 0.25099(12) 0.0414(3) Uani d . 1 1
H H4 0.5688 0.9982 0.2832 0.050 Uiso calc R 1 1
C C5 0.67851(12) 0.6964(3) 0.31244(11) 0.0427(3) Uani d . 1 1
H H5 0.6968 0.7092 0.3870 0.051 Uiso calc R 1 1
C C6 0.72895(11) 0.5077(3) 0.26594(10) 0.0376(3) Uani d . 1 1
H H6 0.7814 0.3905 0.3087 0.045 Uiso calc R 1 1
C C7 0.75788(10) 0.2993(3) 0.10215(10) 0.0311(3) Uani d . 1 1
C C8 0.91038(11) -0.0700(3) 0.08957(11) 0.0377(3) Uani d . 1 1
H H8A 0.9495 -0.2334 0.1244 0.045 Uiso calc R 1 1
H H8B 0.8470 -0.1342 0.0344 0.045 Uiso calc R 1 1
C C9 0.98021(10) 0.0896(3) 0.03740(11) 0.0382(3) Uani d . 1 1
H H9A 1.0415 0.1647 0.0924 0.046 Uiso calc R 1 1
H H9B 0.9397 0.2452 -0.0023 0.046 Uiso calc R 1 1
O O1 0.73074(8) 0.2677(2) 0.00745(7) 0.0429(3) Uani d . 1 1
S S1 0.86863(3) 0.12549(8) 0.18584(3) 0.03886(13) 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C6 C1 C2 . . 119.39(12)
C6 C1 C7 . . 122.48(11)
C2 C1 C7 . . 118.13(11)
C3 C2 C1 . . 119.98(12)
C3 C2 H2 . . 120.0
C1 C2 H2 . . 120.0
C4 C3 C2 . . 120.21(13)
C4 C3 H3 . . 119.9
C2 C3 H3 . . 119.9
C5 C4 C3 . . 120.04(13)
C5 C4 H4 . . 120.0
C3 C4 H4 . . 120.0
C4 C5 C6 . . 120.26(13)
C4 C5 H5 . . 119.9
C6 C5 H5 . . 119.9
C5 C6 C1 . . 120.06(13)
C5 C6 H6 . . 120.0
C1 C6 H6 . . 120.0
O1 C7 C1 . . 122.90(12)
O1 C7 S1 . . 121.94(10)
C1 C7 S1 . . 115.15(9)
C9 C8 S1 . . 113.65(10)
C9 C8 H8A . . 108.8
S1 C8 H8A . . 108.8
C9 C8 H8B . . 108.8
S1 C8 H8B . . 108.8
H8A C8 H8B . . 107.7
C8 C9 C9 . 3_755 111.70(14)
C8 C9 H9A . . 109.3
C9 C9 H9A 3_755 . 109.3
C8 C9 H9B . . 109.3
C9 C9 H9B 3_755 . 109.3
H9A C9 H9B . . 107.9
C7 S1 C8 . . 100.22(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C6 . 1.3913(17)
C1 C2 . 1.3916(17)
C1 C7 . 1.4912(17)
C2 C3 . 1.3841(19)
C2 H2 . 0.9500
C3 C4 . 1.382(2)
C3 H3 . 0.9500
C4 C5 . 1.377(2)
C4 H4 . 0.9500
C5 C6 . 1.384(2)
C5 H5 . 0.9500
C6 H6 . 0.9500
C7 O1 . 1.2117(15)
C7 S1 . 1.7761(13)
C8 C9 . 1.5204(19)
C8 S1 . 1.8053(14)
C8 H8A . 0.9900
C8 H8B . 0.9900
C9 C9 3_755 1.526(3)
C9 H9A . 0.9900
C9 H9B . 0.9900
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
_geom_hbond_publ_flag
C4 H4 Cg1 2_655 0.95 3.09 3.8810(15) 141 yes
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 . 2.1(2)
C7 C1 C2 C3 . -177.31(13)
C1 C2 C3 C4 . -0.1(2)
C2 C3 C4 C5 . -1.8(2)
C3 C4 C5 C6 . 1.7(2)
C4 C5 C6 C1 . 0.4(2)
C2 C1 C6 C5 . -2.3(2)
C7 C1 C6 C5 . 177.12(14)
C6 C1 C7 O1 . 174.55(14)
C2 C1 C7 O1 . -6.1(2)
C6 C1 C7 S1 . -6.66(18)
C2 C1 C7 S1 . 172.72(11)
S1 C8 C9 C9 3_755 175.95(10)
O1 C7 S1 C8 . -0.26(14)
C1 C7 S1 C8 . -179.07(11)
C9 C8 S1 C7 . 83.52(11)
