#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/04/2230433.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_2230433
loop_
_publ_author_name
'Li, Haiyun'
'Wang, Guannan'
'Xiao, Xunwen'
_publ_section_title
;
 4-(2-Cyanoethylsulfanyl)-5'-(pyridin-4-yl)tetrathiafulvalene
;
_journal_coeditor_code           NG5167
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1467
_journal_paper_doi               10.1107/S1600536811018800
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H10 N2 S5'
_chemical_formula_moiety         'C14 H10 N2 S5'
_chemical_formula_sum            'C14 H10 N2 S5'
_chemical_formula_weight         366.54
_chemical_name_common
;
4-(2-Cyanoethylsulfanyl)-5'-(pyridin-4-yl)tetrathiafulvalene
;
_chemical_name_systematic
;
3-({2-[4-(pyridin-4-yl)-2H-1,3-dithiol-2-ylidene]-2H-1,3-dithiol-
4-yl}sulfanyl)propanenitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.775(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6231(18)
_cell_length_b                   10.7197(12)
_cell_length_c                   9.9211(12)
_cell_measurement_reflns_used    5787
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1549.8(3)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalStructure (Rigaku, 2005)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7658
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  0.856
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.315
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0609
_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)+(0.0484P)²+1.3388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                2268
_reflns_number_total             2869
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng5167.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230433
_cod_database_fobs_code          2230433
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.45140(7) 0.17432(9) 0.11234(11) 0.0324(3) Uani d . 1 1 . .
S S2 0.57042(7) -0.02950(10) 0.22543(11) 0.0362(3) Uani d . 1 1 . .
S S3 0.61033(7) 0.25532(10) -0.08148(12) 0.0377(3) Uani d . 1 1 . .
S S4 0.72869(7) 0.05022(10) 0.03146(11) 0.0361(3) Uani d . 1 1 . .
S S5 0.87437(8) 0.10167(11) -0.16139(12) 0.0438(3) Uani d . 1 1 . .
N N1 0.1558(3) 0.1902(4) 0.3981(5) 0.0555(11) Uani d . 1 1 . .
N N2 0.9396(3) 0.4512(4) -0.1998(5) 0.0619(12) Uani d . 1 1 . .
C C1 0.1881(3) 0.2455(5) 0.2923(6) 0.0601(14) Uani d . 1 1 . .
H H1 0.1532 0.3107 0.2508 0.072 Uiso calc R 1 1 . .
C C2 0.2690(3) 0.2145(4) 0.2386(5) 0.0459(12) Uani d . 1 1 . .
H H2 0.2865 0.2562 0.1615 0.055 Uiso calc R 1 1 . .
C C3 0.3240(3) 0.1224(4) 0.2984(4) 0.0323(9) Uani d . 1 1 . .
C C4 0.2907(3) 0.0618(4) 0.4090(5) 0.0451(12) Uani d . 1 1 . .
H H4 0.3242 -0.0035 0.4528 0.054 Uiso calc R 1 1 . .
C C5 0.2082(3) 0.0989(5) 0.4532(5) 0.0529(14) Uani d . 1 1 . .
H H5 0.1873 0.0568 0.5278 0.063 Uiso calc R 1 1 . .
C C6 0.4131(3) 0.0883(4) 0.2484(4) 0.0321(9) Uani d . 1 1 . .
C C7 0.4680(3) -0.0036(4) 0.2963(4) 0.0345(10) Uani d . 1 1 . .
H H7 0.4512 -0.0538 0.3680 0.041 Uiso calc R 1 1 . .
C C8 0.5581(2) 0.0973(3) 0.1123(4) 0.0284(9) Uani d . 1 1 . .
C C9 0.6232(3) 0.1293(4) 0.0326(4) 0.0298(9) Uani d . 1 1 . .
C C10 0.7170(3) 0.2350(4) -0.1449(4) 0.0348(10) Uani d . 1 1 . .
H H10 0.7363 0.2886 -0.2120 0.042 Uiso calc R 1 1 . .
C C11 0.7705(3) 0.1427(4) -0.0967(4) 0.0350(10) Uani d . 1 1 . .
C C12 0.9586(3) 0.1601(5) -0.0324(5) 0.0484(12) Uani d . 1 1 . .
H H12A 0.9549 0.1103 0.0498 0.058 Uiso calc R 1 1 . .
H H12B 1.0199 0.1478 -0.0632 0.058 Uiso calc R 1 1 . .
C C13 0.9480(3) 0.2965(5) 0.0034(5) 0.0511(13) Uani d . 1 1 . .
H H13A 0.8915 0.3064 0.0491 0.061 Uiso calc R 1 1 . .
H H13B 0.9995 0.3207 0.0676 0.061 Uiso calc R 1 1 . .
C C14 0.9445(3) 0.3823(5) -0.1136(5) 0.0458(12) Uani d . 1 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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 C8 . . 95.29(18) ?
C7 S2 C8 . . 95.10(19) ?
C10 S3 C9 . . 94.88(19) ?
C9 S4 C11 . . 95.20(19) ?
C11 S5 C12 . . 102.3(2) ?
C1 N1 C5 . . 115.0(4) ?
N1 C1 C2 . . 124.8(5) ?
N1 C1 H1 . . 117.6 ?
C2 C1 H1 . . 117.6 ?
C3 C2 C1 . . 119.8(4) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C2 C3 C4 . . 116.2(4) ?
C2 C3 C6 . . 122.2(4) ?
C4 C3 C6 . . 121.6(4) ?
C5 C4 C3 . . 119.2(4) ?
C5 C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
N1 C5 C4 . . 124.9(5) ?
N1 C5 H5 . . 117.6 ?
C4 C5 H5 . . 117.6 ?
C7 C6 C3 . . 125.8(4) ?
C7 C6 S1 . . 116.0(3) ?
C3 C6 S1 . . 118.2(3) ?
C6 C7 S2 . . 119.3(3) ?
C6 C7 H7 . . 120.3 ?
S2 C7 H7 . . 120.3 ?
C9 C8 S2 . . 122.4(3) ?
C9 C8 S1 . . 123.7(3) ?
S2 C8 S1 . . 113.8(2) ?
C8 C9 S4 . . 123.3(3) ?
C8 C9 S3 . . 122.3(3) ?
S4 C9 S3 . . 114.3(2) ?
C11 C10 S3 . . 118.8(3) ?
C11 C10 H10 . . 120.6 ?
S3 C10 H10 . . 120.6 ?
C10 C11 S5 . . 123.9(3) ?
C10 C11 S4 . . 116.8(3) ?
S5 C11 S4 . . 119.1(2) ?
C13 C12 S5 . . 115.0(3) ?
C13 C12 H12A . . 108.5 ?
S5 C12 H12A . . 108.5 ?
C13 C12 H12B . . 108.5 ?
S5 C12 H12B . . 108.5 ?
H12A C12 H12B . . 107.5 ?
C14 C13 C12 . . 114.5(4) ?
C14 C13 H13A . . 108.6 ?
C12 C13 H13A . . 108.6 ?
C14 C13 H13B . . 108.6 ?
C12 C13 H13B . . 108.6 ?
H13A C13 H13B . . 107.6 ?
N2 C14 C13 . . 177.0(5) ?
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 . 1.764(4) ?
S1 C8 . 1.765(4) ?
S2 C7 . 1.729(4) ?
S2 C8 . 1.762(4) ?
S3 C10 . 1.744(4) ?
S3 C9 . 1.762(4) ?
S4 C9 . 1.761(4) ?
S4 C11 . 1.761(4) ?
S5 C11 . 1.753(4) ?
S5 C12 . 1.812(5) ?
N1 C1 . 1.327(7) ?
N1 C5 . 1.331(7) ?
N2 C14 . 1.128(6) ?
C1 C2 . 1.377(6) ?
C1 H1 . 0.9400 ?
C2 C3 . 1.377(6) ?
C2 H2 . 0.9400 ?
C3 C4 . 1.398(6) ?
C3 C6 . 1.478(5) ?
C4 C5 . 1.376(6) ?
C4 H4 . 0.9400 ?
C5 H5 . 0.9400 ?
C6 C7 . 1.333(6) ?
C7 H7 . 0.9400 ?
C8 C9 . 1.333(5) ?
C10 C11 . 1.326(6) ?
C10 H10 . 0.9400 ?
C12 C13 . 1.515(6) ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C13 C14 . 1.479(7) ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . 0.3(8) ?
N1 C1 C2 C3 . . . . -2.1(8) ?
C1 C2 C3 C4 . . . . 2.7(7) ?
C1 C2 C3 C6 . . . . -177.7(4) ?
C2 C3 C4 C5 . . . . -1.7(6) ?
C6 C3 C4 C5 . . . . 178.7(4) ?
C1 N1 C5 C4 . . . . 0.7(8) ?
C3 C4 C5 N1 . . . . 0.0(8) ?
C2 C3 C6 C7 . . . . -176.5(4) ?
C4 C3 C6 C7 . . . . 3.1(7) ?
C2 C3 C6 S1 . . . . 2.9(6) ?
C4 C3 C6 S1 . . . . -177.5(3) ?
C8 S1 C6 C7 . . . . -4.2(4) ?
C8 S1 C6 C3 . . . . 176.3(3) ?
C3 C6 C7 S2 . . . . -179.7(3) ?
S1 C6 C7 S2 . . . . 0.9(5) ?
C8 S2 C7 C6 . . . . 3.0(4) ?
C7 S2 C8 C9 . . . . 175.7(4) ?
C7 S2 C8 S1 . . . . -5.7(3) ?
C6 S1 C8 C9 . . . . -175.4(4) ?
C6 S1 C8 S2 . . . . 6.1(2) ?
S2 C8 C9 S4 . . . . -0.5(5) ?
S1 C8 C9 S4 . . . . -178.9(2) ?
S2 C8 C9 S3 . . . . 179.4(2) ?
S1 C8 C9 S3 . . . . 1.0(5) ?
C11 S4 C9 C8 . . . . 178.6(4) ?
C11 S4 C9 S3 . . . . -1.4(3) ?
C10 S3 C9 C8 . . . . -179.1(4) ?
C10 S3 C9 S4 . . . . 0.8(3) ?
C9 S3 C10 C11 . . . . 0.3(4) ?
S3 C10 C11 S5 . . . . 173.8(2) ?
S3 C10 C11 S4 . . . . -1.4(5) ?
C12 S5 C11 C10 . . . . 106.0(4) ?
C12 S5 C11 S4 . . . . -79.0(3) ?
C9 S4 C11 C10 . . . . 1.6(4) ?
C9 S4 C11 S5 . . . . -173.7(3) ?
C11 S5 C12 C13 . . . . -53.5(4) ?
S5 C12 C13 C14 . . . . -53.5(5) ?
C12 C13 C14 N2 . . . . 152(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656723
