#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/58/2225815.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_2225815
loop_
_publ_author_name
'Hou, Rui-Bin'
'Li, Bao'
'Yin, Bing-Zhu'
'Wu, Li-Xin'
_publ_section_title
;
 6,7-Bis(methylsulfanyl)-2,3-[(3,6,9-trioxaundecane-1,11-diyl)bis(sulfanediylmethylene)]-1,4,5,8-tetrathiafulvalene
;
_journal_coeditor_code           CV2706
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1044
_journal_paper_doi               10.1107/S160053681001192X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H26 O3 S8'
_chemical_formula_moiety         'C18 H26 O3 S8'
_chemical_formula_sum            'C18 H26 O3 S8'
_chemical_formula_weight         546.87
_chemical_name_systematic
;
6,7-Bis(methylsulfanyl)-2,3-[(3,6,9-trioxaundecane-1,11-
diyl)bis(sulfanediylmethylene)]-1,4,5,8-tetrathiafulvalene
;
_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                98.37(2)
_cell_angle_beta                 112.112(18)
_cell_angle_gamma                103.94(2)
_cell_formula_units_Z            2
_cell_length_a                   9.715(5)
_cell_length_b                   11.585(7)
_cell_length_c                   12.548(5)
_cell_measurement_reflns_used    8201
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.09
_cell_volume                     1225.2(11)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC and Rigaku, 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      290(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_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  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12067
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  0.9223
_exptl_absorpt_correction_T_min  0.9091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.190
_refine_diff_density_min         -0.840
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         5535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0606P)²+0.6546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1254
_reflns_number_gt                4519
_reflns_number_total             5535
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv2706.cif
_cod_data_source_block           I
_cod_original_cell_volume        1225.3(11)
_cod_database_code               2225815
_cod_database_fobs_code          2225815
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 0.8329(4) 0.2619(3) -0.0795(3) 0.0673(8) Uani d . 1 . .
H H1A 0.9100 0.3281 -0.0122 0.101 Uiso calc R 1 . .
H H1B 0.8797 0.2016 -0.0963 0.101 Uiso calc R 1 . .
H H1C 0.7472 0.2243 -0.0620 0.101 Uiso calc R 1 . .
C C2 0.6741(3) 0.4211(2) -0.1600(2) 0.0461(6) Uani d . 1 . .
C C3 0.6468(3) 0.6002(2) -0.0284(2) 0.0378(5) Uani d . 1 . .
C C4 0.6879(3) 0.7034(2) 0.0568(2) 0.0375(5) Uani d . 1 . .
C C5 0.8608(3) 0.9048(2) 0.2248(2) 0.0377(5) Uani d . 1 . .
C C6 1.0049(3) 0.9939(2) 0.3263(2) 0.0453(6) Uani d . 1 . .
H H6A 1.0222 0.9641 0.3970 0.054 Uiso calc R 1 . .
H H6B 0.9875 1.0724 0.3417 0.054 Uiso calc R 1 . .
C C7 1.1338(4) 1.0744(4) 0.1696(3) 0.0672(9) Uani d . 1 . .
H H7A 1.1946 1.0522 0.1287 0.081 Uiso calc R 1 . .
H H7B 1.0238 1.0324 0.1167 0.081 Uiso calc R 1 . .
C C8 1.1631(4) 1.2111(4) 0.1912(4) 0.0809(11) Uani d . 1 . .
H H8A 1.2668 1.2551 0.2548 0.097 Uiso calc R 1 . .
H H8B 1.1577 1.2362 0.1197 0.097 Uiso calc R 1 . .
C C9 1.0704(4) 1.3669(3) 0.2552(3) 0.0717(9) Uani d . 1 . .
H H9A 1.0745 1.4025 0.1906 0.086 Uiso calc R 1 . .
H H9B 1.1688 1.4080 0.3253 0.086 Uiso calc R 1 . .
C C10 0.9373(4) 1.3834(3) 0.2801(3) 0.0631(8) Uani d . 1 . .
H H10A 0.9445 1.4696 0.2948 0.076 Uiso calc R 1 . .
H H10B 0.8383 1.3365 0.2124 0.076 Uiso calc R 1 . .
C C11 0.8268(4) 1.3533(3) 0.4170(3) 0.0631(8) Uani d . 1 . .
H H11A 0.7245 1.3175 0.3497 0.076 Uiso calc R 1 . .
H H11B 0.8427 1.4396 0.4478 0.076 Uiso calc R 1 . .
C C12 0.8366(4) 1.2872(3) 0.5112(3) 0.0684(9) Uani d . 1 . .
H H12A 0.9438 1.3157 0.5724 0.082 Uiso calc R 1 . .
H H12B 0.7701 1.3060 0.5479 0.082 Uiso calc R 1 . .
C C13 0.6293(4) 1.0953(3) 0.4346(3) 0.0646(8) Uani d . 1 . .
H H13A 0.5700 1.1524 0.4205 0.077 Uiso calc R 1 . .
H H13B 0.6215 1.0642 0.5006 0.077 Uiso calc R 1 . .
C C14 0.5624(4) 0.9902(3) 0.3249(3) 0.0579(7) Uani d . 1 . .
H H14A 0.4659 0.9349 0.3191 0.070 Uiso calc R 1 . .
H H14B 0.6358 0.9445 0.3335 0.070 Uiso calc R 1 . .
C C15 0.7020(3) 1.0495(2) 0.1709(2) 0.0424(5) Uani d . 1 . .
H H15A 0.6948 1.0792 0.1011 0.051 Uiso calc R 1 . .
H H15B 0.7895 1.1095 0.2398 0.051 Uiso calc R 1 . .
C C16 0.7328(3) 0.9291(2) 0.1574(2) 0.0369(5) Uani d . 1 . .
C C17 0.5549(3) 0.4512(3) -0.2335(2) 0.0542(7) Uani d . 1 . .
C C18 0.2899(5) 0.2958(4) -0.4241(4) 0.0993(14) Uani d . 1 . .
H H18A 0.3042 0.2321 -0.3839 0.149 Uiso calc R 1 . .
H H18B 0.2354 0.2598 -0.5086 0.149 Uiso calc R 1 . .
H H18C 0.2296 0.3380 -0.3983 0.149 Uiso calc R 1 . .
O O1 1.0472(3) 1.2390(2) 0.2231(2) 0.0649(6) Uani d . 1 . .
O O2 0.9459(2) 1.3412(2) 0.38150(17) 0.0585(5) Uani d . 1 . .
O O3 0.7891(2) 1.1573(2) 0.46389(19) 0.0605(5) Uani d . 1 . .
S S1 0.76152(11) 0.32107(7) -0.20652(7) 0.0659(2) Uani d . 1 . .
S S2 0.75246(8) 0.49614(6) -0.00808(5) 0.04786(17) Uani d . 1 . .
S S3 0.85994(8) 0.75086(6) 0.19036(5) 0.04658(17) Uani d . 1 . .
S S4 1.18116(8) 1.01831(8) 0.30089(7) 0.0583(2) Uani d . 1 . .
S S5 0.52206(8) 1.03736(6) 0.18849(6) 0.04905(17) Uani d . 1 . .
S S6 0.57706(7) 0.80320(6) 0.04603(6) 0.04656(17) Uani d . 1 . .
S S7 0.48777(8) 0.55840(7) -0.16902(6) 0.05239(18) Uani d . 1 . .
S S8 0.47241(13) 0.40014(12) -0.39012(7) 0.0970(4) 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 ?
C17 C2 S1 . . 124.5(2) ?
C17 C2 S2 . . 116.3(2) ?
S1 C2 S2 . . 119.01(17) ?
C4 C3 S2 . . 121.99(19) ?
C4 C3 S7 . . 124.10(19) ?
S2 C3 S7 . . 113.89(13) ?
C3 C4 S6 . . 123.71(19) ?
C3 C4 S3 . . 122.82(19) ?
S6 C4 S3 . . 113.46(13) ?
C16 C5 C6 . . 126.9(2) ?
C16 C5 S3 . . 116.77(18) ?
C6 C5 S3 . . 116.37(18) ?
C5 C6 S4 . . 114.01(17) ?
C5 C6 H6A . . 108.7 ?
S4 C6 H6A . . 108.7 ?
C5 C6 H6B . . 108.7 ?
S4 C6 H6B . . 108.7 ?
H6A C6 H6B . . 107.6 ?
C8 C7 S4 . . 115.4(2) ?
C8 C7 H7A . . 108.4 ?
S4 C7 H7A . . 108.4 ?
C8 C7 H7B . . 108.4 ?
S4 C7 H7B . . 108.4 ?
H7A C7 H7B . . 107.5 ?
O1 C8 C7 . . 108.5(3) ?
O1 C8 H8A . . 110.0 ?
C7 C8 H8A . . 110.0 ?
O1 C8 H8B . . 110.0 ?
C7 C8 H8B . . 110.0 ?
H8A C8 H8B . . 108.4 ?
O1 C9 C10 . . 108.2(2) ?
O1 C9 H9A . . 110.1 ?
C10 C9 H9A . . 110.1 ?
O1 C9 H9B . . 110.1 ?
C10 C9 H9B . . 110.1 ?
H9A C9 H9B . . 108.4 ?
O2 C10 C9 . . 107.8(3) ?
O2 C10 H10A . . 110.2 ?
C9 C10 H10A . . 110.2 ?
O2 C10 H10B . . 110.2 ?
C9 C10 H10B . . 110.2 ?
H10A C10 H10B . . 108.5 ?
O2 C11 C12 . . 107.1(3) ?
O2 C11 H11A . . 110.3 ?
C12 C11 H11A . . 110.3 ?
O2 C11 H11B . . 110.3 ?
C12 C11 H11B . . 110.3 ?
H11A C11 H11B . . 108.6 ?
O3 C12 C11 . . 111.5(2) ?
O3 C12 H12A . . 109.3 ?
C11 C12 H12A . . 109.3 ?
O3 C12 H12B . . 109.3 ?
C11 C12 H12B . . 109.3 ?
H12A C12 H12B . . 108.0 ?
O3 C13 C14 . . 109.6(2) ?
O3 C13 H13A . . 109.7 ?
C14 C13 H13A . . 109.7 ?
O3 C13 H13B . . 109.7 ?
C14 C13 H13B . . 109.7 ?
H13A C13 H13B . . 108.2 ?
C13 C14 S5 . . 114.0(2) ?
C13 C14 H14A . . 108.8 ?
S5 C14 H14A . . 108.8 ?
C13 C14 H14B . . 108.8 ?
S5 C14 H14B . . 108.8 ?
H14A C14 H14B . . 107.7 ?
C16 C15 S5 . . 112.39(16) ?
C16 C15 H15A . . 109.1 ?
S5 C15 H15A . . 109.1 ?
C16 C15 H15B . . 109.1 ?
S5 C15 H15B . . 109.1 ?
H15A C15 H15B . . 107.9 ?
C5 C16 C15 . . 127.2(2) ?
C5 C16 S6 . . 116.68(18) ?
C15 C16 S6 . . 115.94(18) ?
C2 C17 S8 . . 124.0(2) ?
C2 C17 S7 . . 117.57(19) ?
S8 C17 S7 . . 118.18(19) ?
S8 C18 H18A . . 109.5 ?
S8 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
S8 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C9 O1 C8 . . 113.5(3) ?
C10 O2 C11 . . 114.0(2) ?
C13 O3 C12 . . 113.9(3) ?
C2 S1 C1 . . 101.77(14) ?
C3 S2 C2 . . 95.28(13) ?
C4 S3 C5 . . 94.67(11) ?
C7 S4 C6 . . 103.95(13) ?
C14 S5 C15 . . 102.32(13) ?
C4 S6 C16 . . 94.86(12) ?
C3 S7 C17 . . 94.12(13) ?
C18 S8 C17 . . 102.48(18) ?
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 . 1.790(4) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C17 . 1.341(4) ?
C2 S1 . 1.748(3) ?
C2 S2 . 1.753(3) ?
C3 C4 . 1.345(3) ?
C3 S2 . 1.750(3) ?
C3 S7 . 1.753(2) ?
C4 S6 . 1.746(2) ?
C4 S3 . 1.756(2) ?
C5 C16 . 1.337(3) ?
C5 C6 . 1.492(3) ?
C5 S3 . 1.770(3) ?
C6 S4 . 1.821(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.504(5) ?
C7 S4 . 1.798(4) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 O1 . 1.419(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 O1 . 1.416(4) ?
C9 C10 . 1.487(5) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 O2 . 1.408(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 O2 . 1.415(4) ?
C11 C12 . 1.485(5) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 O3 . 1.425(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 O3 . 1.420(4) ?
C13 C14 . 1.503(5) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 S5 . 1.803(3) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.496(3) ?
C15 S5 . 1.818(3) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 S6 . 1.767(3) ?
C17 S8 . 1.761(3) ?
C17 S7 . 1.765(3) ?
C18 S8 . 1.742(5) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744809
