#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/52/2225291.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_2225291
loop_
_publ_author_name
'Xiao, Qi'
'Liu, Rui'
'Li, Yu-Hao'
'Chen, Hong-Bin'
'Zhu, Hong-Jun'
_publ_section_title
;
 1,2-Bis(4-ethynylphenyl)disulfane
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o606
_journal_paper_doi               10.1107/S1600536810004721
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H10 S2'
_chemical_formula_moiety         'C16 H10 S2'
_chemical_formula_sum            'C16 H10 S2'
_chemical_formula_weight         266.36
_chemical_melting_point          391
_chemical_name_common            1,2-bis(4-ethynylphenyl)disulfane
_chemical_name_systematic
;
1,2-bis(4-ethynylphenyl)disulfane
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.92(3)
_cell_angle_beta                 99.29(3)
_cell_angle_gamma                104.45(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9810(10)
_cell_length_b                   8.881(2)
_cell_length_c                   13.269(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     667.7(3)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo,1995)'
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2887
_diffrn_reflns_theta_full        25.96
_diffrn_reflns_theta_max         25.96
_diffrn_reflns_theta_min         1.57
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.376
_exptl_absorpt_correction_T_max  0.8956
_exptl_absorpt_correction_T_min  0.8642
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.400
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2620
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0604
_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)+(0.0600P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1944
_reflns_number_gt                1969
_reflns_number_total             2620
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            im2180.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        667.7(2)
_cod_database_code               2225291
_cod_database_fobs_code          2225291
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.0903(2) 0.50232(15) 0.20304(9) 0.0594(4) Uani d . 1 . .
C C1 0.8307(10) 0.2056(7) 0.5708(4) 0.0674(13) Uani d D 1 . .
S S2 -0.1535(2) 0.31363(17) 0.11850(10) 0.0619(4) Uani d . 1 . .
C C2 0.7075(8) 0.2523(6) 0.5110(4) 0.0561(11) Uani d . 1 . .
C C3 0.5594(8) 0.3096(5) 0.4359(3) 0.0479(10) Uani d . 1 . .
C C4 0.3177(9) 0.2406(6) 0.4127(4) 0.0606(12) Uani d . 1 . .
H H4A 0.2522 0.1573 0.4461 0.073 Uiso calc R 1 . .
C C5 0.1745(8) 0.2953(6) 0.3402(4) 0.0571(11) Uani d . 1 . .
H H5A 0.0137 0.2475 0.3242 0.069 Uiso calc R 1 . .
C C6 0.2705(8) 0.4209(5) 0.2916(3) 0.0476(10) Uani d . 1 . .
C C7 0.5073(8) 0.4891(6) 0.3143(4) 0.0575(11) Uani d . 1 . .
H H7A 0.5722 0.5718 0.2803 0.069 Uiso calc R 1 . .
C C8 0.6516(8) 0.4362(6) 0.3876(4) 0.0578(11) Uani d . 1 . .
H H8A 0.8116 0.4863 0.4042 0.069 Uiso calc R 1 . .
C C9 0.3291(10) 0.0564(7) -0.3034(4) 0.0686(14) Uani d D 1 . .
C C10 0.2502(8) 0.0917(6) -0.2347(4) 0.0561(11) Uani d . 1 . .
C C11 0.1571(8) 0.1440(5) -0.1475(3) 0.0503(10) Uani d . 1 . .
C C12 0.2959(8) 0.2639(5) -0.0736(3) 0.0522(10) Uani d . 1 . .
H H12A 0.4508 0.3089 -0.0791 0.063 Uiso calc R 1 . .
C C13 0.2091(8) 0.3179(6) 0.0079(4) 0.0567(11) Uani d . 1 . .
H H13A 0.3057 0.3986 0.0570 0.068 Uiso calc R 1 . .
C C14 -0.0207(8) 0.2532(5) 0.0175(3) 0.0490(10) Uani d . 1 . .
C C15 -0.1597(8) 0.1311(5) -0.0558(4) 0.0542(11) Uani d . 1 . .
H H15A -0.3133 0.0845 -0.0493 0.065 Uiso calc R 1 . .
C C16 -0.0744(8) 0.0782(6) -0.1376(3) 0.0542(11) Uani d . 1 . .
H H16A -0.1714 -0.0022 -0.1869 0.065 Uiso calc R 1 . .
H H9 0.385(8) 0.019(5) -0.362(2) 0.065 Uiso d D 1 . .
H H1 0.947(6) 0.176(6) 0.617(3) 0.065 Uiso d D 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 0.0706(8) 0.0593(7) 0.0513(7) 0.0280(6) 0.0044(5) 0.0062(5)
C1 0.069(3) 0.071(3) 0.062(3) 0.021(3) 0.006(3) 0.012(3)
S2 0.0527(7) 0.0807(9) 0.0534(7) 0.0229(6) 0.0062(5) 0.0069(6)
C2 0.055(3) 0.060(3) 0.049(3) 0.014(2) 0.004(2) 0.002(2)
C3 0.051(2) 0.055(2) 0.042(2) 0.023(2) 0.0102(18) 0.0059(18)
C4 0.059(3) 0.064(3) 0.060(3) 0.017(2) 0.010(2) 0.018(2)
C5 0.044(2) 0.062(3) 0.059(3) 0.011(2) 0.001(2) 0.006(2)
C6 0.050(2) 0.045(2) 0.046(2) 0.0144(18) 0.0069(18) 0.0012(18)
C7 0.059(3) 0.058(3) 0.057(3) 0.013(2) 0.013(2) 0.017(2)
C8 0.047(2) 0.063(3) 0.057(3) 0.006(2) 0.004(2) 0.010(2)
C9 0.072(3) 0.070(3) 0.068(3) 0.024(3) 0.021(3) 0.005(3)
C10 0.059(3) 0.056(3) 0.053(3) 0.017(2) 0.004(2) 0.009(2)
C11 0.053(3) 0.053(2) 0.049(2) 0.021(2) 0.0062(19) 0.0157(19)
C12 0.046(2) 0.058(3) 0.050(2) 0.014(2) 0.0022(19) 0.007(2)
C13 0.043(2) 0.067(3) 0.053(3) 0.010(2) -0.0027(19) 0.005(2)
C14 0.057(3) 0.054(2) 0.040(2) 0.023(2) 0.0075(18) 0.0115(18)
C15 0.040(2) 0.060(3) 0.057(3) 0.010(2) -0.0013(19) 0.010(2)
C16 0.052(3) 0.058(3) 0.048(2) 0.016(2) -0.0040(19) 0.001(2)
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'
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
_geom_angle_publ_flag
C6 S1 S2 . . 104.69(15) ?
C2 C1 H1 . . 173(3) ?
C14 S2 S1 . . 105.55(17) ?
C1 C2 C3 . . 178.8(5) ?
C8 C3 C4 . . 118.7(4) ?
C8 C3 C2 . . 121.0(4) ?
C4 C3 C2 . . 120.3(4) ?
C5 C4 C3 . . 120.4(4) ?
C5 C4 H4A . . 119.8 ?
C3 C4 H4A . . 119.8 ?
C6 C5 C4 . . 120.0(4) ?
C6 C5 H5A . . 120.0 ?
C4 C5 H5A . . 120.0 ?
C7 C6 C5 . . 119.7(4) ?
C7 C6 S1 . . 118.7(3) ?
C5 C6 S1 . . 121.5(3) ?
C6 C7 C8 . . 120.6(4) ?
C6 C7 H7A . . 119.7 ?
C8 C7 H7A . . 119.7 ?
C3 C8 C7 . . 120.5(4) ?
C3 C8 H8A . . 119.8 ?
C7 C8 H8A . . 119.8 ?
C10 C9 H9 . . 175(3) ?
C9 C10 C11 . . 177.3(6) ?
C12 C11 C16 . . 118.5(4) ?
C12 C11 C10 . . 120.2(4) ?
C16 C11 C10 . . 121.4(4) ?
C13 C12 C11 . . 121.0(4) ?
C13 C12 H12A . . 119.5 ?
C11 C12 H12A . . 119.5 ?
C12 C13 C14 . . 120.6(4) ?
C12 C13 H13A . . 119.7 ?
C14 C13 H13A . . 119.7 ?
C13 C14 C15 . . 118.5(4) ?
C13 C14 S2 . . 124.8(4) ?
C15 C14 S2 . . 116.7(4) ?
C16 C15 C14 . . 121.0(4) ?
C16 C15 H15A . . 119.5 ?
C14 C15 H15A . . 119.5 ?
C15 C16 C11 . . 120.4(4) ?
C15 C16 H16A . . 119.8 ?
C11 C16 H16A . . 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C6 . 1.786(4) ?
S1 S2 . 2.030(2) ?
C1 C2 . 1.169(7) ?
C1 H1 . 0.956(10) ?
S2 C14 . 1.774(4) ?
C2 C3 . 1.436(6) ?
C3 C8 . 1.382(6) ?
C3 C4 . 1.393(6) ?
C4 C5 . 1.384(6) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.383(6) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.366(6) ?
C7 C8 . 1.386(6) ?
C7 H7A . 0.9300 ?
C8 H8A . 0.9300 ?
C9 C10 . 1.147(7) ?
C9 H9 . 0.959(10) ?
C10 C11 . 1.452(7) ?
C11 C12 . 1.379(6) ?
C11 C16 . 1.394(6) ?
C12 C13 . 1.374(6) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.382(6) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.386(6) ?
C15 C16 . 1.368(7) ?
C15 H15A . 0.9300 ?
C16 H16A . 0.9300 ?
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
C13 H13A S1 . 0.9300 2.7100 3.216(5) 115.00 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744466
