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Volume 69 
Part 4 
Page o571  
April 2013  

Received 13 March 2013
Accepted 17 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 113 K
Mean [sigma](C-C) = 0.003 Å
R = 0.031
wR = 0.076
Data-to-parameter ratio = 12.8
Details
Open access

(E)-[2-(1,3-Dithiolan-2-ylidene)hydrazinylidene](3-fluorophenyl)methyl 3-fluorobenzoate

aDepartment of Chemistry and Chemical Engineering, Jining University, Qufu 273155, People's Republic of China
Correspondence e-mail: yinling_1109@163.com

In the title compound, C17H12F2N2O2S2, the conformation of the dithiacyclopentane ring is a half-chair, with a total puckering amplitude QT = 0.460 (1) Å. [pi]-[pi] interactions [centroid-centroid distance = 3.585 (9) Å between the fluorophenyl rings of neighbouring molecules] and C-H...N and C-H...O interactions help to stabilize the crystal structure and form ladders along the c axis.

Related literature

For the use of dithiolan heterocyclic compounds as broad-spectrum fungicides, see: Tanaka et al. (1976[Tanaka, H., Araki, F., Harada, T. & Kurono, H. (1976). Jpn Patent No. 51151326A.]); Wang et al. (1994[Wang, Y., Li, Z. H. & Gao, N. (1994). Yaoxue Xuebao, 29, 78-80.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12F2N2O2S2

  • Mr = 378.41

  • Triclinic, [P \overline 1]

  • a = 9.124 (4) Å

  • b = 9.757 (4) Å

  • c = 10.738 (4) Å

  • [alpha] = 104.592 (3)°

  • [beta] = 110.326 (5)°

  • [gamma] = 101.194 (4)°

  • V = 824.6 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.36 mm-1

  • T = 113 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Rigaku Saturn724 CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009)[Rigaku/MSC (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.] Tmin = 0.932, Tmax = 0.932

  • 7057 measured reflections

  • 2896 independent reflections

  • 2098 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.076

  • S = 0.96

  • 2896 reflections

  • 226 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9B...O2i 0.97 2.49 3.280 (2) 138
C10-H10B...O2ii 0.97 2.46 3.248 (2) 138
C13-H13A...N1iii 0.93 2.50 3.424 (3) 176
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x+1, y, z; (iii) -x, -y+2, -z+2.

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2009)[Rigaku/MSC (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]; cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5300 ).


Acknowledgements

The author thanks the Jining University Foundation (No. 2012YYJJ07) for financial support of this work.

References

Rigaku/MSC (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tanaka, H., Araki, F., Harada, T. & Kurono, H. (1976). Jpn Patent No. 51151326A.
Wang, Y., Li, Z. H. & Gao, N. (1994). Yaoxue Xuebao, 29, 78-80.


Acta Cryst (2013). E69, o571  [ doi:10.1107/S1600536813007319 ]

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