#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/34/2223499.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_2223499
loop_
_publ_author_name
'Hou, Rui-Bin'
'Li, Bao'
'Che, Tie'
'Yin, Bing-Zhu'
'Wu, Li-Xin'
_publ_section_title
13-[4,5-Bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-6-oxa-3,9,12,14-tetrathiabicyclo[9.3.0]tetradec-1(11)-ene
_journal_coeditor_code           NG2642
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2538
_journal_paper_doi               10.1107/S1600536809037301
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H18 O S8'
_chemical_formula_moiety         'C14 H18 O S8'
_chemical_formula_sum            'C14 H18 O S8'
_chemical_formula_weight         458.76
_chemical_name_common
;
2,3-(5-Oxa-2,8-dithiacycloundecane)-6,7-dimethylthio-1,4,5,8-
tetrathiafulvalene
;
_chemical_name_systematic
;
13-[4,5-bis(methylsulfanyl)-1,3-dithiol-2-ylidene]-6-oxa-3,9,12,14-
tetrathiabicyclo[9.3.0]tetradec-1(11)-ene
;
_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
_cell_angle_alpha                105.00(3)
_cell_angle_beta                 97.83(3)
_cell_angle_gamma                112.22(3)
_cell_formula_units_Z            2
_cell_length_a                   8.4542(17)
_cell_length_b                   10.158(2)
_cell_length_c                   13.612(3)
_cell_measurement_reflns_used    8201
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.09
_cell_volume                     1008.8(5)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_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  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9961
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_T_max  0.9013
_exptl_absorpt_correction_T_min  0.8862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.093
_refine_diff_density_min         -0.637
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4572
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0884P)²+0.6622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1702
_reflns_number_gt                3655
_reflns_number_total             4572
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2642.cif
_cod_data_source_block           I
_cod_original_cell_volume        1008.8(3)
_cod_database_code               2223499
_cod_database_fobs_code          2223499
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
C C1 0.0932(11) 0.6629(10) 0.3460(6) 0.147(3) Uani d U 1 . .
H H1A 0.1923 0.7484 0.3443 0.220 Uiso calc R 1 . .
H H1B 0.0094 0.6954 0.3720 0.220 Uiso calc R 1 . .
H H1C 0.0378 0.5904 0.2761 0.220 Uiso calc R 1 . .
C C2 0.3190(6) 0.5333(5) 0.3702(3) 0.0698(11) Uani d . 1 . .
C C3 0.4341(5) 0.4102(4) 0.2243(3) 0.0507(7) Uani d . 1 . .
C C4 0.4512(4) 0.3545(3) 0.1275(2) 0.0461(7) Uani d . 1 . .
C C5 0.3940(4) 0.2608(3) -0.0741(2) 0.0413(6) Uani d . 1 . .
C C6 0.2894(5) 0.2050(4) -0.1861(3) 0.0525(8) Uani d . 1 . .
H H6A 0.3691 0.2087 -0.2314 0.063 Uiso calc R 1 . .
H H6B 0.2366 0.2724 -0.1949 0.063 Uiso calc R 1 . .
C C7 0.2424(8) -0.0950(6) -0.2145(6) 0.1025(17) Uani d U 1 . .
H H7A 0.3145 -0.0519 -0.1423 0.123 Uiso calc R 1 . .
H H7B 0.1583 -0.1969 -0.2240 0.123 Uiso calc R 1 . .
C C8 0.3534(6) -0.1067(5) -0.2800(5) 0.0943(17) Uani d . 1 . .
H H8A 0.2905 -0.1288 -0.3517 0.113 Uiso calc R 1 . .
H H8B 0.3794 -0.1915 -0.2786 0.113 Uiso calc R 1 . .
C C9 0.6658(6) 0.0075(5) -0.2091(4) 0.0740(12) Uani d . 1 . .
H H9A 0.7526 0.0358 -0.2487 0.089 Uiso calc R 1 . .
H H9B 0.6321 -0.0978 -0.2166 0.089 Uiso calc R 1 . .
C C10 0.7491(5) 0.1017(4) -0.0953(3) 0.0649(10) Uani d . 1 . .
H H10A 0.8265 0.0635 -0.0660 0.078 Uiso calc R 1 . .
H H10B 0.6563 0.0882 -0.0589 0.078 Uiso calc R 1 . .
C C11 0.7040(4) 0.3605(4) -0.0996(3) 0.0469(7) Uani d . 1 . .
H H11A 0.7589 0.4682 -0.0874 0.056 Uiso calc R 1 . .
H H11B 0.6438 0.3094 -0.1740 0.056 Uiso calc R 1 . .
C C12 0.5700(4) 0.3284(3) -0.0371(2) 0.0407(6) Uani d . 1 . .
C C13 0.4928(6) 0.6013(4) 0.4070(3) 0.0661(10) Uani d . 1 . .
C C14 0.7619(13) 0.8815(12) 0.4955(7) 0.176(4) Uani d U 1 . .
H H14A 0.8239 0.8368 0.4545 0.264 Uiso calc R 1 . .
H H14B 0.8442 0.9598 0.5587 0.264 Uiso calc R 1 . .
H H14C 0.7053 0.9239 0.4552 0.264 Uiso calc R 1 . .
O O1 0.5140(4) 0.0229(3) -0.2531(2) 0.0707(7) Uani d . 1 . .
S S1 0.1683(2) 0.5780(2) 0.43099(13) 0.1162(6) Uani d . 1 . .
S S2 0.22953(15) 0.37585(11) 0.25246(8) 0.0674(3) Uani d . 1 . .
S S3 0.26931(11) 0.23691(10) 0.01898(7) 0.0513(2) Uani d . 1 . .
S S4 0.11564(12) 0.01405(12) -0.22817(9) 0.0704(3) Uani d . 1 . .
S S5 0.87487(12) 0.30094(10) -0.06741(8) 0.0602(3) Uani d . 1 . .
S S6 0.65644(11) 0.38520(10) 0.10015(6) 0.0504(2) Uani d . 1 . .
S S7 0.61409(14) 0.52278(11) 0.33593(7) 0.0619(3) Uani d . 1 . .
S S8 0.6096(2) 0.74971(15) 0.52682(9) 0.1030(5) Uani d . 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
_geom_angle_publ_flag
S1 C1 H1A . . 109.5 ?
S1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
S1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C13 C2 S1 . . 125.9(3) ?
C13 C2 S2 . . 117.2(3) ?
S1 C2 S2 . . 116.8(3) ?
C4 C3 S2 . . 123.3(3) ?
C4 C3 S7 . . 123.7(3) ?
S2 C3 S7 . . 112.98(18) ?
C3 C4 S3 . . 122.6(3) ?
C3 C4 S6 . . 123.2(3) ?
S3 C4 S6 . . 114.08(18) ?
C12 C5 C6 . . 127.3(3) ?
C12 C5 S3 . . 116.9(2) ?
C6 C5 S3 . . 115.8(2) ?
C5 C6 S4 . . 113.5(3) ?
C5 C6 H6A . . 108.9 ?
S4 C6 H6A . . 108.9 ?
C5 C6 H6B . . 108.9 ?
S4 C6 H6B . . 108.9 ?
H6A C6 H6B . . 107.7 ?
C8 C7 S4 . . 119.7(5) ?
C8 C7 H7A . . 107.4 ?
S4 C7 H7A . . 107.4 ?
C8 C7 H7B . . 107.4 ?
S4 C7 H7B . . 107.4 ?
H7A C7 H7B . . 106.9 ?
C7 C8 O1 . . 114.6(4) ?
C7 C8 H8A . . 108.6 ?
O1 C8 H8A . . 108.6 ?
C7 C8 H8B . . 108.6 ?
O1 C8 H8B . . 108.6 ?
H8A C8 H8B . . 107.6 ?
O1 C9 C10 . . 113.4(3) ?
O1 C9 H9A . . 108.9 ?
C10 C9 H9A . . 108.9 ?
O1 C9 H9B . . 108.9 ?
C10 C9 H9B . . 108.9 ?
H9A C9 H9B . . 107.7 ?
C9 C10 S5 . . 116.1(3) ?
C9 C10 H10A . . 108.3 ?
S5 C10 H10A . . 108.3 ?
C9 C10 H10B . . 108.3 ?
S5 C10 H10B . . 108.3 ?
H10A C10 H10B . . 107.4 ?
C12 C11 S5 . . 113.4(2) ?
C12 C11 H11A . . 108.9 ?
S5 C11 H11A . . 108.9 ?
C12 C11 H11B . . 108.9 ?
S5 C11 H11B . . 108.9 ?
H11A C11 H11B . . 107.7 ?
C5 C12 C11 . . 127.1(3) ?
C5 C12 S6 . . 117.2(2) ?
C11 C12 S6 . . 115.7(2) ?
C2 C13 S8 . . 125.2(3) ?
C2 C13 S7 . . 116.7(3) ?
S8 C13 S7 . . 117.7(3) ?
S8 C14 H14A . . 109.5 ?
S8 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
S8 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C8 O1 C9 . . 114.7(4) ?
C2 S1 C1 . . 100.8(3) ?
C3 S2 C2 . . 94.04(19) ?
C4 S3 C5 . . 94.20(15) ?
C6 S4 C7 . . 102.0(2) ?
C10 S5 C11 . . 102.29(17) ?
C4 S6 C12 . . 93.92(15) ?
C3 S7 C13 . . 94.02(19) ?
C14 S8 C13 . . 104.6(3) ?
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
C1 S1 . 1.794(9) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C13 . 1.319(7) ?
C2 S1 . 1.744(4) ?
C2 S2 . 1.768(4) ?
C3 C4 . 1.344(5) ?
C3 S2 . 1.747(4) ?
C3 S7 . 1.756(4) ?
C4 S3 . 1.747(3) ?
C4 S6 . 1.753(3) ?
C5 C12 . 1.335(4) ?
C5 C6 . 1.496(4) ?
C5 S3 . 1.762(3) ?
C6 S4 . 1.814(4) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.397(8) ?
C7 S4 . 1.833(6) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 O1 . 1.405(6) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 O1 . 1.421(5) ?
C9 C10 . 1.495(6) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 S5 . 1.798(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.498(4) ?
C11 S5 . 1.809(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 S6 . 1.763(3) ?
C13 S8 . 1.752(4) ?
C13 S7 . 1.765(4) ?
C14 S8 . 1.665(9) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
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
C7 H7B S2 2 0.97 3.00 3.793(6) 140.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743329
