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Volume 69 
Part 5 
Page o714  
May 2013  

Received 2 April 2013
Accepted 4 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 113 K
Mean [sigma](C-C) = 0.003 Å
R = 0.030
wR = 0.074
Data-to-parameter ratio = 18.1
Details
Open access

(3-Chlorophenyl)[(E)-2-(1,3-dithiolan-2-ylidene)hydrazinylidene]methyl 3-chlorobenzoate

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, C17H12Cl2N2O2S2, the dithiacyclopentane ring has an envelope conformation with one of the methylene C atoms as the flap. The chlorophenyl rings make a dihedral angle of 82.63 (7)°. In the crystal, [pi]-[pi] interactions between the benzene rings of neighbouring molecules [centroid-centroid distance = 3.547 (2) Å] link the molecules into inversion dimers. Weak non-classical C-H...X (X = O, N, Cl) interactions further consolidate the packing, forming a layer structure parallel to (110).

Related literature

For applications of heterocyclic dithiolane compounds, 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.]). For the crystal structure of (E)-[2-(1,3-dithiolan-2-ylidene)hydrazinylidene](3-fluorophenyl)methyl 3-fluorobenzoate, see: Yin (2013[Yin, L. (2013). Acta Cryst. E69, o571.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12Cl2N2O2S2

  • Mr = 411.31

  • Triclinic, [P \overline 1]

  • a = 8.960 (5) Å

  • b = 9.944 (6) Å

  • c = 11.128 (6) Å

  • [alpha] = 104.174 (8)°

  • [beta] = 111.041 (7)°

  • [gamma] = 99.410 (2)°

  • V = 861.9 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.63 mm-1

  • T = 113 K

  • 0.34 × 0.25 × 0.20 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku/MSC, 2009[Rigaku/MSC (2009). CrystalClear-SM Expert. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.884, Tmax = 0.884

  • 11088 measured reflections

  • 4080 independent reflections

  • 3115 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.074

  • S = 0.95

  • 4080 reflections

  • 226 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10A...N1i 0.95 2.59 3.534 (2) 173
C14-H14A...Cl1ii 0.95 2.80 3.727 (2) 165
C16-H16B...O2iii 0.99 2.48 3.274 (3) 137
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x, y+1, z; (iii) x+1, y, z.

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2009[Rigaku/MSC (2009). CrystalClear-SM Expert. 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: CV5400 ).


Acknowledgements

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

References

Rigaku/MSC (2009). CrystalClear-SM Expert. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [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.
Yin, L. (2013). Acta Cryst. E69, o571.  [CrossRef] [details]


Acta Cryst (2013). E69, o714  [ doi:10.1107/S1600536813009239 ]

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