#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/90/2209012.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_2209012
loop_
_publ_author_name
'Isabelle Malfant '
'Laure Vendier'
'Oleg A. D'Yachenko'
'Alexander I. Kotov'
_publ_section_title
;
 The π-donor
 4,5;4',5'-bis(dioxane-1,4-diyl-2,3-dithio)tetrathiafulvalene
;
_journal_coeditor_code           TK2005
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1948
_journal_page_last               o1950
_journal_paper_doi               10.1107/S1600536806007161
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H12 O4 S8'
_chemical_formula_moiety         'C14 H12 O4 S8'
_chemical_formula_sum            'C14 H12 O4 S8'
_chemical_formula_weight         500.72
_chemical_name_systematic
;
4,5;4',5'-bis(dioxane-1,4-diyl-2,3-dithio)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                106.009(11)
_cell_angle_beta                 90.107(12)
_cell_angle_gamma                103.453(12)
_cell_formula_units_Z            2
_cell_length_a                   6.3867(7)
_cell_length_b                   11.0716(13)
_cell_length_c                   14.1462(16)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    180
_cell_measurement_theta_max      26.1
_cell_measurement_theta_min      1.7
_cell_volume                     932.8(2)
_computing_cell_refinement       'IPDS Software'
_computing_data_collection       'IPDS Software (Stoe, 1996)'
_computing_data_reduction        'XRED (Stoe, 1996)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device       'Stoe IPDS'
_diffrn_measurement_method       φ
_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  0.042
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7398
_diffrn_reflns_theta_full        24.1
_diffrn_reflns_theta_max         24.1
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  4
_diffrn_standards_number         200
_exptl_absorpt_coefficient_mu    0.977
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            orange--yellow
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.97
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.97
_refine_ls_R_factor_all          0.037
_refine_ls_R_factor_gt           0.026
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0364P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.058
_refine_ls_wR_factor_ref         0.060
_reflns_number_gt                2225
_reflns_number_total             2733
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2005.cif
_cod_data_source_block           I
_cod_original_cell_volume        932.78(18)
_cod_database_code               2209012
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
C C1 0.5883(4) -0.07113(19) 0.12969(15) 0.0150(5) Uani d . 1
C C2 0.6865(4) 0.0104(2) 0.21550(15) 0.0164(5) Uani d . 1
C C3 0.5017(4) -0.20101(19) -0.05357(15) 0.0160(5) Uani d . 1
C C4 0.3127(4) -0.2170(2) -0.01319(15) 0.0173(5) Uani d . 1
C C5 0.9444(4) 0.20572(19) 0.33307(14) 0.0140(5) Uani d . 1
C C6 0.7574(4) 0.1947(2) 0.37568(15) 0.0158(5) Uani d . 1
C C7 0.3319(4) -0.4177(2) -0.22100(16) 0.0208(5) Uani d . 1
H H7 0.2401 -0.4078 -0.2726 0.025 Uiso calc R 1
C C8 0.1844(4) -0.4514(2) -0.14301(16) 0.0210(5) Uani d . 1
H H8 0.0637 -0.5233 -0.1768 0.025 Uiso calc R 1
C C9 1.1541(4) 0.3042(2) 0.51084(15) 0.0163(5) Uani d . 1
H H9 1.2873 0.3557 0.5506 0.02 Uiso calc R 1
C C10 0.9671(4) 0.3515(2) 0.56182(15) 0.0176(5) Uani d . 1
H H10 1.0108 0.4463 0.5801 0.021 Uiso calc R 1
C C11 0.5316(4) -0.5621(2) -0.19549(19) 0.0303(6) Uani d . 1
H H11A 0.6513 -0.4931 -0.1594 0.036 Uiso calc R 1
H H11B 0.5885 -0.6352 -0.2295 0.036 Uiso calc R 1
C C12 0.3742(5) -0.6013(2) -0.12472(19) 0.0315(6) Uani d . 1
H H12A 0.2575 -0.6731 -0.1601 0.038 Uiso calc R 1
H H12B 0.4457 -0.6294 -0.077 0.038 Uiso calc R 1
C C13 1.1188(5) 0.1488(2) 0.59729(17) 0.0298(6) Uani d . 1
H H13A 1.2437 0.2003 0.6414 0.036 Uiso calc R 1
H H13B 1.11 0.0582 0.5907 0.036 Uiso calc R 1
C C14 0.9190(5) 0.1837(2) 0.63898(18) 0.0335(7) Uani d . 1
H H14A 0.7943 0.131 0.5952 0.04 Uiso calc R 1
H H14B 0.9017 0.166 0.7024 0.04 Uiso calc R 1
O O1 0.4305(3) -0.51882(15) -0.26616(11) 0.0256(4) Uani d . 1
O O2 0.2891(3) -0.49318(14) -0.07471(11) 0.0241(4) Uani d . 1
O O3 1.1416(3) 0.17242(14) 0.50242(11) 0.0214(4) Uani d . 1
O O4 0.9314(3) 0.31811(15) 0.65083(10) 0.0243(4) Uani d . 1
S S1 0.73390(10) -0.11429(5) 0.02499(4) 0.01928(15) Uani d . 1
S S2 0.31341(10) -0.15205(5) 0.11500(4) 0.02103(15) Uani d . 1
S S3 0.96642(10) 0.07803(5) 0.23044(4) 0.01908(15) Uani d . 1
S S4 0.55056(10) 0.05490(5) 0.32345(4) 0.01799(15) Uani d . 1
S S5 0.54342(11) -0.26324(5) -0.17755(4) 0.02258(16) Uani d . 1
S S6 0.07267(11) -0.31886(6) -0.07728(4) 0.02771(17) Uani d . 1
S S7 1.17817(10) 0.32490(5) 0.38831(4) 0.01849(15) Uani d . 1
S S8 0.70916(10) 0.30355(6) 0.48407(4) 0.02335(16) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C2 C1 S2 123.50(18)
C2 C1 S1 121.62(19)
S2 C1 S1 114.71(11)
C1 C2 S3 122.21(18)
C1 C2 S4 123.75(19)
S3 C2 S4 114.00(11)
C4 C3 S5 126.00(17)
C4 C3 S1 117.72(16)
S5 C3 S1 116.24(13)
C3 C4 S6 123.41(16)
C3 C4 S2 117.62(17)
S6 C4 S2 118.22(14)
C6 C5 S3 117.34(16)
C6 C5 S7 122.42(16)
S3 C5 S7 119.15(13)
C5 C6 S8 124.65(17)
C5 C6 S4 117.54(15)
S8 C6 S4 117.67(13)
O1 C7 C8 111.80(19)
O1 C7 S5 109.16(17)
C8 C7 S5 115.07(14)
O1 C7 H7 106.8
C8 C7 H7 106.8
S5 C7 H7 106.8
O2 C8 C7 112.1(2)
O2 C8 S6 109.16(14)
C7 C8 S6 112.73(16)
O2 C8 H8 107.5
C7 C8 H8 107.5
S6 C8 H8 107.5
O3 C9 C10 113.11(18)
O3 C9 S7 107.57(13)
C10 C9 S7 112.84(16)
O3 C9 H9 107.7
C10 C9 H9 107.7
S7 C9 H9 107.7
O4 C10 C9 112.10(19)
O4 C10 S8 110.19(15)
C9 C10 S8 115.40(14)
O4 C10 H10 106.2
C9 C10 H10 106.2
S8 C10 H10 106.2
O1 C11 C12 110.9(2)
O1 C11 H11A 109.5
C12 C11 H11A 109.5
O1 C11 H11B 109.5
C12 C11 H11B 109.5
H11A C11 H11B 108
O2 C12 C11 109.4(2)
O2 C12 H12A 109.8
C11 C12 H12A 109.8
O2 C12 H12B 109.8
C11 C12 H12B 109.8
H12A C12 H12B 108.2
O3 C13 C14 109.5(2)
O3 C13 H13A 109.8
C14 C13 H13A 109.8
O3 C13 H13B 109.8
C14 C13 H13B 109.8
H13A C13 H13B 108.2
O4 C14 C13 110.4(2)
O4 C14 H14A 109.6
C13 C14 H14A 109.6
O4 C14 H14B 109.6
C13 C14 H14B 109.6
H14A C14 H14B 108.1
C7 O1 C11 112.29(17)
C8 O2 C12 110.44(17)
C9 O3 C13 110.46(16)
C10 O4 C14 112.40(16)
C3 S1 C1 94.21(11)
C4 S2 C1 94.44(10)
C5 S3 C2 93.03(10)
C6 S4 C2 92.79(10)
C3 S5 C7 104.94(10)
C4 S6 C8 97.45(11)
C5 S7 C9 96.55(10)
C6 S8 C10 104.25(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.345(3)
C1 S2 1.759(2)
C1 S1 1.763(2)
C2 S3 1.758(2)
C2 S4 1.766(2)
C3 C4 1.332(3)
C3 S5 1.744(2)
C3 S1 1.760(2)
C4 S6 1.752(2)
C4 S2 1.756(2)
C5 C6 1.334(3)
C5 S3 1.757(2)
C5 S7 1.758(2)
C6 S8 1.747(2)
C6 S4 1.761(2)
C7 O1 1.412(3)
C7 C8 1.520(3)
C7 S5 1.862(2)
C7 H7 0.98
C8 O2 1.408(3)
C8 S6 1.807(2)
C8 H8 0.98
C9 O3 1.414(3)
C9 C10 1.519(3)
C9 S7 1.812(2)
C9 H9 0.98
C10 O4 1.412(3)
C10 S8 1.863(2)
C10 H10 0.98
C11 O1 1.432(3)
C11 C12 1.497(4)
C11 H11A 0.97
C11 H11B 0.97
C12 O2 1.438(3)
C12 H12A 0.97
C12 H12B 0.97
C13 O3 1.438(3)
C13 C14 1.494(4)
C13 H13A 0.97
C13 H13B 0.97
C14 O4 1.435(3)
C14 H14A 0.97
C14 H14B 0.97
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8611489
