#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/38/2223832.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_2223832
loop_
_publ_author_name
'Hou, Rui-Bin'
'Li, Bao'
'Chen, Tie'
'Yin, Bing-Zhu'
'Wu, Li-Xin'
_publ_section_title
2,3-[(3,6-Dioxaoctane-1,8-diyl)bis(sulfanediylmethylene)]-6,7-bis(methylsulfanyl)-1,4,5,8-tetrathiafulvalene
_journal_coeditor_code           HG2569
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2783
_journal_paper_doi               10.1107/S1600536809041804
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H22 O2 S8'
_chemical_formula_moiety         'C16 H22 O2 S8'
_chemical_formula_sum            'C16 H22 O2 S8'
_chemical_formula_weight         502.82
_chemical_name_systematic
;
2,3-[(3,6-Dioxaoctane-1,8-diyl)bis(sulfanediylmethylene)]-6,7-
bis(methylsulfanyl)-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                98.49(3)
_cell_angle_beta                 105.58(3)
_cell_angle_gamma                113.33(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1748(18)
_cell_length_b                   10.177(2)
_cell_length_c                   14.273(3)
_cell_measurement_reflns_used    9031
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.10
_cell_volume                     1129.1(6)
_computing_cell_refinement       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8752
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_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    0.800
_exptl_absorpt_correction_T_max  0.9101
_exptl_absorpt_correction_T_min  0.8962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.890
_refine_diff_density_min         -0.468
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0734P)²+0.3957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                3345
_reflns_number_total             3948
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            hg2569.cif
_cod_data_source_block           I
_cod_original_cell_volume        1129.1(4)
_cod_database_code               2223832
_cod_database_fobs_code          2223832
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 1.3188(5) 1.3283(5) 1.4807(3) 0.0753(11) Uani d . 1 . .
H H1A 1.3746 1.2709 1.4639 0.113 Uiso calc R 1 . .
H H1B 1.3938 1.4078 1.5421 0.113 Uiso calc R 1 . .
H H1C 1.2897 1.3696 1.4264 0.113 Uiso calc R 1 . .
C C2 1.0102(4) 1.0784(3) 1.3801(2) 0.0407(6) Uani d . 1 . .
C C3 0.9324(3) 0.8957(3) 1.2084(2) 0.0391(6) Uani d . 1 . .
C C4 0.9441(3) 0.8476(3) 1.1199(2) 0.0385(6) Uani d . 1 . .
C C5 1.0573(4) 0.8202(3) 0.9740(2) 0.0390(6) Uani d . 1 . .
C C6 1.1888(4) 0.8549(3) 0.9252(2) 0.0468(7) Uani d . 1 . .
H H6A 1.2329 0.9591 0.9262 0.056 Uiso calc R 1 . .
H H6B 1.1347 0.7950 0.8548 0.056 Uiso calc R 1 . .
C C7 1.2681(5) 0.6217(4) 0.9544(3) 0.0651(9) Uani d . 1 . .
H H7A 1.3327 0.5927 1.0056 0.078 Uiso calc R 1 . .
H H7B 1.1542 0.5855 0.9562 0.078 Uiso calc R 1 . .
C C8 1.2573(7) 0.5487(5) 0.8545(4) 0.0880(13) Uani d . 1 . .
H H8A 1.3674 0.5934 0.8475 0.106 Uiso calc R 1 . .
H H8B 1.2227 0.4433 0.8467 0.106 Uiso calc R 1 . .
C C9 1.0860(8) 0.4660(7) 0.6849(4) 0.1128(19) Uani d . 1 . .
H H9A 1.1787 0.4945 0.6595 0.135 Uiso calc R 1 . .
H H9B 1.0565 0.3662 0.6920 0.135 Uiso calc R 1 . .
C C10 0.9459(9) 0.4676(9) 0.6175(4) 0.131(3) Uani d . 1 . .
H H10A 0.8974 0.3828 0.5580 0.157 Uiso calc R 1 . .
H H10B 0.9870 0.5570 0.5958 0.157 Uiso calc R 1 . .
C C11 0.7180(7) 0.3431(5) 0.6827(4) 0.0914(14) Uani d . 1 . .
H H11A 0.7741 0.2801 0.6902 0.110 Uiso calc R 1 . .
H H11B 0.6044 0.2836 0.6321 0.110 Uiso calc R 1 . .
C C12 0.7074(4) 0.4011(4) 0.7818(3) 0.0623(9) Uani d . 1 . .
H H12A 0.8214 0.4560 0.8325 0.075 Uiso calc R 1 . .
H H12B 0.6441 0.3173 0.8033 0.075 Uiso calc R 1 . .
C C13 0.7897(4) 0.7058(4) 0.8160(2) 0.0529(7) Uani d . 1 . .
H H13A 0.8643 0.7022 0.7798 0.063 Uiso calc R 1 . .
H H13B 0.7503 0.7771 0.7975 0.063 Uiso calc R 1 . .
C C14 0.8897(4) 0.7596(3) 0.9285(2) 0.0396(6) Uani d . 1 . .
C C15 0.8397(4) 1.0198(3) 1.3351(2) 0.0443(6) Uani d . 1 . .
C C16 0.5893(6) 1.1099(6) 1.2868(4) 0.0912(14) Uani d . 1 . .
H H16A 0.6654 1.1911 1.2698 0.137 Uiso calc R 1 . .
H H16B 0.5123 1.1380 1.3080 0.137 Uiso calc R 1 . .
H H16C 0.5258 1.0238 1.2283 0.137 Uiso calc R 1 . .
O O1 1.1364(5) 0.5674(4) 0.7799(2) 0.0980(10) Uani d . 1 . .
O O2 0.8095(6) 0.4633(5) 0.6516(3) 0.1180(14) Uani d . 1 . .
S S1 1.12983(11) 1.21034(9) 1.49854(6) 0.0562(2) Uani d . 1 . .
S S2 1.10990(9) 0.99321(8) 1.32208(5) 0.0452(2) Uani d . 1 . .
S S3 1.13813(9) 0.87356(9) 1.10784(5) 0.0456(2) Uani d . 1 . .
S S4 1.36459(10) 0.82043(9) 0.98642(7) 0.0545(2) Uani d . 1 . .
S S5 0.60655(10) 0.52141(11) 0.77587(7) 0.0664(3) Uani d . 1 . .
S S6 0.76769(9) 0.74362(8) 1.00707(5) 0.0456(2) Uani d . 1 . .
S S7 0.74108(9) 0.86596(9) 1.22600(6) 0.0486(2) Uani d . 1 . .
S S8 0.71029(12) 1.06618(12) 1.38866(7) 0.0675(3) 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 ?
C15 C2 S1 . . 124.6(2) ?
C15 C2 S2 . . 116.2(2) ?
S1 C2 S2 . . 118.48(17) ?
C4 C3 S7 . . 124.5(2) ?
C4 C3 S2 . . 123.0(2) ?
S7 C3 S2 . . 112.44(15) ?
C3 C4 S6 . . 123.6(2) ?
C3 C4 S3 . . 122.6(2) ?
S6 C4 S3 . . 113.75(15) ?
C14 C5 C6 . . 127.7(3) ?
C14 C5 S3 . . 116.9(2) ?
C6 C5 S3 . . 115.3(2) ?
C5 C6 S4 . . 113.8(2) ?
C5 C6 H6A . . 108.8 ?
S4 C6 H6A . . 108.8 ?
C5 C6 H6B . . 108.8 ?
S4 C6 H6B . . 108.8 ?
H6A C6 H6B . . 107.7 ?
C8 C7 S4 . . 114.3(3) ?
C8 C7 H7A . . 108.7 ?
S4 C7 H7A . . 108.7 ?
C8 C7 H7B . . 108.7 ?
S4 C7 H7B . . 108.7 ?
H7A C7 H7B . . 107.6 ?
O1 C8 C7 . . 108.0(3) ?
O1 C8 H8A . . 110.1 ?
C7 C8 H8A . . 110.1 ?
O1 C8 H8B . . 110.1 ?
C7 C8 H8B . . 110.1 ?
H8A C8 H8B . . 108.4 ?
C10 C9 O1 . . 108.7(5) ?
C10 C9 H9A . . 109.9 ?
O1 C9 H9A . . 109.9 ?
C10 C9 H9B . . 109.9 ?
O1 C9 H9B . . 109.9 ?
H9A C9 H9B . . 108.3 ?
C9 C10 O2 . . 118.5(4) ?
C9 C10 H10A . . 107.7 ?
O2 C10 H10A . . 107.7 ?
C9 C10 H10B . . 107.7 ?
O2 C10 H10B . . 107.7 ?
H10A C10 H10B . . 107.1 ?
O2 C11 C12 . . 109.1(4) ?
O2 C11 H11A . . 109.9 ?
C12 C11 H11A . . 109.9 ?
O2 C11 H11B . . 109.9 ?
C12 C11 H11B . . 109.9 ?
H11A C11 H11B . . 108.3 ?
C11 C12 S5 . . 113.1(3) ?
C11 C12 H12A . . 109.0 ?
S5 C12 H12A . . 108.9 ?
C11 C12 H12B . . 108.9 ?
S5 C12 H12B . . 109.0 ?
H12A C12 H12B . . 107.8 ?
C14 C13 S5 . . 113.2(2) ?
C14 C13 H13A . . 108.9 ?
S5 C13 H13A . . 108.9 ?
C14 C13 H13B . . 108.9 ?
S5 C13 H13B . . 108.9 ?
H13A C13 H13B . . 107.7 ?
C5 C14 C13 . . 127.3(3) ?
C5 C14 S6 . . 117.3(2) ?
C13 C14 S6 . . 115.4(2) ?
C2 C15 S8 . . 124.2(2) ?
C2 C15 S7 . . 116.8(2) ?
S8 C15 S7 . . 118.15(17) ?
S8 C16 H16A . . 109.5 ?
S8 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
S8 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C9 O1 C8 . . 110.0(4) ?
C11 O2 C10 . . 121.3(4) ?
C2 S1 C1 . . 102.60(16) ?
C3 S2 C2 . . 94.09(13) ?
C4 S3 C5 . . 94.92(13) ?
C7 S4 C6 . . 102.45(18) ?
C12 S5 C13 . . 101.68(16) ?
C4 S6 C14 . . 94.74(13) ?
C3 S7 C15 . . 93.90(14) ?
C15 S8 C16 . . 101.88(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 . 1.786(4) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C15 . 1.351(4) ?
C2 S1 . 1.741(3) ?
C2 S2 . 1.760(3) ?
C3 C4 . 1.335(4) ?
C3 S7 . 1.753(3) ?
C3 S2 . 1.759(3) ?
C4 S6 . 1.753(3) ?
C4 S3 . 1.753(3) ?
C5 C14 . 1.327(4) ?
C5 C6 . 1.500(4) ?
C5 S3 . 1.763(3) ?
C6 S4 . 1.809(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.465(6) ?
C7 S4 . 1.782(4) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 O1 . 1.411(6) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.391(8) ?
C9 O1 . 1.410(5) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 O2 . 1.448(6) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 O2 . 1.394(6) ?
C11 C12 . 1.493(6) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 S5 . 1.802(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.506(4) ?
C13 S5 . 1.828(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 S6 . 1.767(3) ?
C15 S8 . 1.744(3) ?
C15 S7 . 1.760(3) ?
C16 S8 . 1.806(5) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 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
C8 H8A S5 1_655 0.97 2.94 3.762(5) 143.0
C1 H1C O2 2_777 0.96 2.49 3.379(6) 153.9
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743546
