#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/47/2204742.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_2204742
loop_
_publ_author_name
'Qing-ling Ni'
'Xiu-Jian Wang'
'Jian-Qiang Zeng'
'Hong-Xia Jian'
_publ_section_title
;
 4,4'-Dithiodiphenol: a chain of rings generated by two pairs of
 O---H···O hydrogen bonds
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2318
_journal_page_last               o2320
_journal_paper_doi               10.1107/S1600536804028636
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C12 H10 O2 S2'
_chemical_formula_moiety         'C12 H10 O2 S2'
_chemical_formula_sum            'C12 H10 O2 S2'
_chemical_formula_weight         250.32
_chemical_name_common            'bis(4-hydroxyphenyl) disulfide'
_chemical_name_systematic
;
4,4'-Dithiodiphenol
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 115.09(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.886(4)
_cell_length_b                   10.959(2)
_cell_length_c                   11.263(2)
_cell_measurement_reflns_used    3841
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.02
_cell_measurement_theta_min      2.15
_cell_volume                     2334.7(9)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0153
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6726
_diffrn_reflns_theta_full        27.02
_diffrn_reflns_theta_max         27.02
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Siemens, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0496P)²+0.722P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                2071
_reflns_number_total             2547
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6305.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2204742
_cod_database_fobs_code          2204742
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_occupancy
_atom_site_type_symbol
S1 0.24192(3) 0.11462(5) 0.33220(5) 0.06695(17) Uani d 1 S
S2 0.14322(2) 0.14461(4) 0.18475(5) 0.05762(16) Uani d 1 S
O1 0.43270(7) 0.05363(14) 0.07053(14) 0.0648(4) Uani d 1 O
O2 0.01560(7) -0.33155(12) -0.03513(14) 0.0641(4) Uani d 1 O
C1 0.29650(8) 0.09545(16) 0.24787(16) 0.0503(4) Uani d 1 C
C2 0.33037(10) -0.01454(17) 0.25722(18) 0.0591(4) Uani d 1 C
C3 0.37673(10) -0.02977(17) 0.20021(18) 0.0585(4) Uani d 1 C
C4 0.38735(8) 0.06480(15) 0.12950(16) 0.0481(4) Uani d 1 C
C5 0.35261(9) 0.17381(16) 0.11703(19) 0.0548(4) Uani d 1 C
C6 0.30811(9) 0.19026(17) 0.17761(19) 0.0560(4) Uani d 1 C
C7 0.09625(10) -0.17254(17) -0.0154(2) 0.0601(5) Uani d 1 C
C8 0.04642(8) -0.22269(15) 0.02139(16) 0.0480(4) Uani d 1 C
C9 0.02876(9) -0.16365(17) 0.11104(17) 0.0521(4) Uani d 1 C
C10 0.06040(8) -0.05426(16) 0.16365(16) 0.0513(4) Uani d 1 C
C11 0.10938(8) -0.00209(14) 0.12630(16) 0.0459(4) Uani d 1 C
C12 0.12695(9) -0.06259(17) 0.03597(19) 0.0574(4) Uani d 1 C
H10 0.0489(10) -0.0130(17) 0.2281(18) 0.065(5) Uiso d 1 H
H5 0.3587(10) 0.2384(19) 0.0661(19) 0.071(6) Uiso d 1 H
H9 -0.0032(10) -0.2011(17) 0.1390(18) 0.061(5) Uiso d 1 H
H6 0.2853(11) 0.2677(19) 0.1695(19) 0.069(6) Uiso d 1 H
H7 0.1046(11) -0.211(2) -0.082(2) 0.079(6) Uiso d 1 H
H12 0.1590(12) -0.028(2) 0.012(2) 0.082(6) Uiso d 1 H
H3 0.4009(10) -0.102(2) 0.2084(19) 0.067(6) Uiso d 1 H
H2 0.3240(11) -0.082(2) 0.308(2) 0.072(6) Uiso d 1 H
H11 -0.0109(13) -0.352(2) -0.003(2) 0.082(7) Uiso d 1 H
H1 0.4426(11) -0.016(2) 0.069(2) 0.074(7) Uiso d 1 H
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
_geom_angle_publ_flag
C1 S1 S2 103.77(6) yes
C11 S2 S1 105.17(6) yes
C4 O1 H1 109.7(16) ?
C8 O2 H11 108.2(17) ?
C2 C1 C6 119.33(16) ?
C2 C1 S1 119.12(14) yes
C6 C1 S1 121.49(14) yes
C1 C2 C3 120.57(17) ?
C1 C2 H2 120.8(12) ?
C3 C2 H2 118.6(12) ?
C2 C3 C4 119.56(17) ?
C2 C3 H3 121.5(13) ?
C4 C3 H3 119.0(13) ?
C5 C4 O1 118.08(15) yes
C5 C4 C3 120.31(15) ?
O1 C4 C3 121.61(16) ?
C4 C5 C6 120.06(17) ?
C4 C5 H5 120.5(12) ?
C6 C5 H5 119.5(12) ?
C5 C6 C1 120.11(17) ?
C5 C6 H6 118.7(12) ?
C1 C6 H6 121.2(12) ?
C12 C7 C8 119.86(15) ?
C12 C7 H7 121.1(13) ?
C8 C7 H7 118.7(13) ?
C9 C8 O2 121.94(15) yes
C9 C8 C7 120.13(16) ?
O2 C8 C7 117.93(15) ?
C8 C9 C10 119.81(15) ?
C8 C9 H9 119.2(12) ?
C10 C9 H9 120.9(12) ?
C9 C10 C11 120.72(15) ?
C9 C10 H10 120.2(11) ?
C11 C10 H10 119.0(11) ?
C10 C11 C12 119.01(15) ?
C10 C11 S2 119.54(12) ?
C12 C11 S2 121.29(12) ?
C7 C12 C11 120.46(15) ?
C7 C12 H12 120.9(14) ?
C11 C12 H12 118.6(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.7787(17) yes
S1 S2 2.0524(11) yes
S2 C11 1.7672(17) yes
O1 C4 1.3738(19) yes
O1 H1 0.79(2) ?
O2 C8 1.377(2) yes
O2 H11 0.81(2) ?
C1 C2 1.379(3) ?
C1 C6 1.388(2) ?
C2 C3 1.380(3) ?
C2 H2 0.98(2) ?
C3 C4 1.381(2) ?
C3 H3 0.92(2) ?
C4 C5 1.374(2) ?
C5 C6 1.378(2) ?
C5 H5 0.95(2) ?
C6 H6 0.96(2) ?
C7 C12 1.372(3) ?
C7 C8 1.386(2) ?
C7 H7 0.94(2) ?
C8 C9 1.375(2) ?
C9 C10 1.376(2) ?
C9 H9 0.944(19) ?
C10 C11 1.384(2) ?
C10 H10 0.97(2) ?
C11 C12 1.388(2) ?
C12 H12 0.90(2) ?
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
O1 H1 O2 7_545 0.79(2) 1.99(2) 2.759(2) 162(2)
O2 H11 O1 3_445 0.81(2) 1.99(2) 2.7829(19) 165(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 247149
