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The crystal structure of the title compound, C14H16N2S2, adopts an anti conformation based on the two pyridine rings with respect to the central alkyl chain. The two terminal pyridine rings are almost parallel to each other, with a dihedral angle of 18.1 (4)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027230/hg6103sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027230/hg6103Isup2.hkl
Contains datablock I

CCDC reference: 259574

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.049
  • wR factor = 0.080
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc. PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C14 .. 5.43 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

1,4-Bis(2-pyridylsulfanyl)butane top
Crystal data top
C14H16N2S2F(000) = 584
Mr = 276.41Dx = 1.281 Mg m3
Dm = ?NONE Mg m3
Dm measured by not measured
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 870 reflections
a = 10.979 (5) Åθ = 2.5–18.3°
b = 11.480 (5) ŵ = 0.36 mm1
c = 11.694 (6) ÅT = 273 K
β = 103.508 (8)°Block, colorless
V = 1433.2 (12) Å30.25 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2526 independent reflections
Radiation source: fine-focus sealed tube1168 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.089
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
h = 1213
Tmin = 0.916, Tmax = 0.932k = 1013
5737 measured reflectionsl = 1113
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.01P)2]
where P = (Fo2 + 2Fc2)/3
2526 reflections(Δ/σ)max = 0.002
163 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.20 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S11.06328 (9)0.22782 (8)1.00208 (9)0.0608 (3)
S20.47049 (9)0.00077 (10)0.79680 (8)0.0656 (3)
N10.9271 (3)0.3942 (3)1.0724 (2)0.0461 (8)
N20.6082 (3)0.1300 (3)0.6851 (3)0.0570 (9)
C10.9156 (3)0.4844 (3)1.1419 (3)0.0550 (10)
H10.83860.52221.12830.066*
C21.0104 (4)0.5249 (3)1.2321 (3)0.0634 (11)
H20.99770.58751.27840.076*
C31.1240 (4)0.4698 (4)1.2512 (3)0.0724 (13)
H31.19030.49511.31100.087*
C41.1398 (3)0.3772 (4)1.1819 (3)0.0596 (11)
H41.21600.33821.19420.071*
C51.0383 (4)0.3434 (3)1.0926 (3)0.0438 (9)
C60.9123 (3)0.2107 (3)0.9015 (3)0.0553 (10)
H6A0.87060.28580.89040.066*
H6B0.92480.18570.82580.066*
C70.8278 (3)0.1240 (3)0.9426 (3)0.0511 (10)
H7A0.80900.15221.01480.061*
H7B0.87170.05040.95980.061*
C80.7059 (3)0.1041 (3)0.8516 (3)0.0495 (10)
H8A0.66070.17710.83610.059*
H8B0.72460.07790.77870.059*
C90.6240 (3)0.0147 (3)0.8922 (3)0.0563 (10)
H9A0.61500.03630.97000.068*
H9B0.66600.06020.89880.068*
C100.4966 (4)0.0825 (3)0.6781 (3)0.0441 (9)
C110.3970 (3)0.0951 (3)0.5810 (4)0.0563 (11)
H110.31990.06080.57970.068*
C120.4142 (4)0.1588 (3)0.4875 (4)0.0680 (12)
H120.34850.16930.42180.082*
C130.5298 (5)0.2073 (3)0.4912 (4)0.0734 (13)
H130.54450.24940.42790.088*
C140.6226 (4)0.1915 (3)0.5916 (4)0.0683 (12)
H140.70020.22550.59490.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0477 (6)0.0531 (6)0.0825 (7)0.0004 (5)0.0170 (5)0.0079 (6)
S20.0432 (6)0.0923 (8)0.0608 (6)0.0011 (6)0.0110 (5)0.0090 (6)
N10.040 (2)0.050 (2)0.0494 (19)0.0021 (15)0.0125 (16)0.0009 (17)
N20.046 (2)0.057 (2)0.067 (2)0.0022 (17)0.0115 (18)0.0081 (18)
C10.049 (3)0.057 (3)0.063 (3)0.005 (2)0.022 (2)0.010 (2)
C20.079 (3)0.057 (3)0.061 (3)0.014 (3)0.029 (3)0.012 (2)
C30.061 (3)0.095 (4)0.059 (3)0.022 (3)0.010 (2)0.011 (3)
C40.037 (3)0.078 (3)0.061 (3)0.004 (2)0.007 (2)0.003 (2)
C50.041 (3)0.045 (2)0.049 (2)0.006 (2)0.016 (2)0.0079 (18)
C60.065 (3)0.048 (2)0.054 (2)0.007 (2)0.015 (2)0.010 (2)
C70.054 (3)0.044 (2)0.054 (2)0.0052 (19)0.011 (2)0.0007 (19)
C80.056 (3)0.049 (3)0.043 (2)0.0006 (19)0.009 (2)0.0025 (18)
C90.055 (2)0.069 (3)0.042 (2)0.010 (2)0.0065 (18)0.002 (2)
C100.039 (2)0.044 (2)0.049 (3)0.0055 (19)0.009 (2)0.0054 (18)
C110.045 (3)0.058 (3)0.061 (3)0.001 (2)0.003 (2)0.013 (2)
C120.079 (4)0.062 (3)0.056 (3)0.019 (3)0.001 (3)0.003 (2)
C130.097 (4)0.053 (3)0.076 (3)0.001 (3)0.031 (3)0.007 (2)
C140.057 (3)0.058 (3)0.089 (3)0.006 (2)0.013 (3)0.004 (3)
Geometric parameters (Å, º) top
S1—C51.758 (3)C6—H6B0.9700
S1—C61.806 (3)C7—C81.520 (4)
S2—C91.800 (3)C7—H7A0.9700
S2—C101.754 (3)C7—H7B0.9700
N1—C51.324 (4)C8—C91.511 (4)
N1—C11.340 (4)C8—H8A0.9700
N2—C101.326 (4)C8—H8B0.9700
N2—C141.341 (4)C9—H9A0.9700
C1—C21.379 (4)C9—H9B0.9700
C1—H10.9300C10—C111.388 (4)
C2—C31.369 (5)C11—C121.364 (4)
C2—H20.9300C11—H110.9300
C3—C41.372 (5)C12—C131.377 (5)
C3—H30.9300C12—H120.9300
C4—C51.393 (4)C13—C141.375 (5)
C4—H40.9300C13—H130.9300
C6—C71.514 (4)C14—H140.9300
C6—H6A0.9700
C5—S1—C6103.1 (2)C8—C7—H7B109.1
C9—S2—C10103.9 (2)H7A—C7—H7B107.9
C1—N1—C5116.5 (3)C9—C8—C7111.9 (3)
C10—N2—C14116.7 (3)C9—C8—H8A109.2
N1—C1—C2124.3 (3)C7—C8—H8A109.2
N1—C1—H1117.9C9—C8—H8B109.2
C2—C1—H1117.9C7—C8—H8B109.2
C3—C2—C1117.7 (4)H8A—C8—H8B107.9
C3—C2—H2121.1C8—C9—S2114.3 (2)
C1—C2—H2121.1C8—C9—H9A108.7
C2—C3—C4119.8 (4)S2—C9—H9A108.7
C2—C3—H3120.1C8—C9—H9B108.7
C4—C3—H3120.1S2—C9—H9B108.7
C3—C4—C5118.0 (4)H9A—C9—H9B107.6
C3—C4—H4121.0N2—C10—C11123.3 (3)
C5—C4—H4121.0N2—C10—S2119.4 (3)
N1—C5—C4123.6 (3)C11—C10—S2117.4 (3)
N1—C5—S1119.5 (3)C12—C11—C10118.8 (4)
C4—C5—S1116.9 (3)C12—C11—H11120.6
C7—C6—S1113.7 (2)C10—C11—H11120.6
C7—C6—H6A108.8C11—C12—C13119.3 (4)
S1—C6—H6A108.8C11—C12—H12120.3
C7—C6—H6B108.8C13—C12—H12120.3
S1—C6—H6B108.8C14—C13—C12117.9 (4)
H6A—C6—H6B107.7C14—C13—H13121.1
C6—C7—C8112.4 (3)C12—C13—H13121.1
C6—C7—H7A109.1N2—C14—C13124.1 (4)
C8—C7—H7A109.1N2—C14—H14118.0
C6—C7—H7B109.1C13—C14—H14118.0
C5—N1—C1—C21.1 (5)C7—C8—C9—S2173.0 (2)
N1—C1—C2—C30.6 (5)C10—S2—C9—C876.7 (3)
C1—C2—C3—C40.4 (5)C14—N2—C10—C110.8 (5)
C2—C3—C4—C50.7 (5)C14—N2—C10—S2180.0 (2)
C1—N1—C5—C41.4 (5)C9—S2—C10—N29.5 (3)
C1—N1—C5—S1177.6 (2)C9—S2—C10—C11171.2 (3)
C3—C4—C5—N11.3 (5)N2—C10—C11—C120.4 (5)
C3—C4—C5—S1177.8 (3)S2—C10—C11—C12179.7 (3)
C6—S1—C5—N11.4 (3)C10—C11—C12—C130.8 (5)
C6—S1—C5—C4179.5 (3)C11—C12—C13—C141.6 (5)
C5—S1—C6—C791.4 (2)C10—N2—C14—C130.1 (5)
S1—C6—C7—C8175.2 (2)C12—C13—C14—N21.3 (6)
C6—C7—C8—C9178.3 (3)
 

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