(IUCr) 2-[2-(4-Methylbenzoyl)-3,3-bis(methylsulfanyl)prop-2-enylidene]malononitrile

Volume 64
Part 3
Page o592
March 2008

Received 25 November 2007
Accepted 7 February 2008
Online 15 February 2008

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.006 Å
R = 0.049
wR = 0.156
Data-to-parameter ratio = 14.0
Details

2-[2-(4-Methylbenzoyl)-3,3-bis(methylsulfanyl)prop-2-enylidene]malononitrile

Joseph Nirmala,^a N. V. Unnikrishnan,^a C. V. Asokan,^b E. R. Anabha ^b and C. Sudarsanakumar ^a ^*

^aSchool of Pure and Applied Physics, Mahatma Gandhi University, Kottayam, Kerala, India, and ^bSchool of Chemical Sciences, Mahatma Gandhi University, Kottayam, Kerala, India
Correspondence e-mail: csudarsan1@sify.com

The title compound, C₁₆H₁₄N₂OS₂, is an example of a push-pull butadiene in which the electron-releasing and electron-withdrawing attachments on either end of the butadiene chain enhance the conjugation in the system. The molecules are linked by intermolecular C-HN interactions.

Related literature

For related literature, see: Anabha & Asokan (2006); Dahne (1978); Dastidar et al. (1993); Freier et al. (1999); Homrighausen & Krause Bauer (2004); Michalik et al. (2002).

Experimental

Crystal data

C₁₆H₁₄N₂OS₂
M_r = 314.41
Monoclinic, C 2
a = 16.6050 (13) Å
b = 10.760 (2) Å
c = 9.905 (2) Å
= 110.09 (2)°
V = 1662.0 (5) Å³
Z = 4
Mo K radiation
= 0.32 mm^-1
T = 295 (2) K
0.25 × 0.25 × 0.20 mm

Data collection

MacScience DIPLabo 32001 diffractometer
Absorption correction: none
4433 measured reflections
2717 independent reflections
2583 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.156
S = 1.11
2717 reflections
194 parameters
1 restraint
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.28 e Å^-3
Absolute structure: Flack (1983), with 1210 Friedel pairs
Flack parameter: 0.11 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12BN2ⁱ	0.96	2.49	3.3871	155
Symmetry code: (i) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z-1]$ .

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003) and ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2055 ).

Acknowledgements

The authors acknowledge the National Single Crystal Diffractometer Facility, Department of Studies in Physics, University of Mysore, Manasagangothri, for help with the data collection. One of the authors (JN) is grateful to UGC, New Delhi, Government of India, for providing a teaching fellowship.

References

Anabha, E. R. & Asokan, C. V. (2006). Synthesis, 1, 151-155.
Dahne, S. (1978). Science, 199, 1163-1167.
Dastidar, P., Guru Row, T. N. & Venkatesan, K. (1993). Acta Cryst. B49, 900-905.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Freier, T., Michalik, M. & Peseke, K. (1999). J. Chem. Soc. Perkin Trans. 2, pp. 1265-1271.
Homrighausen, C. L. & Krause Bauer, J. A. (2004). Acta Cryst. E60, o1828-o1829.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
MacScience (2002). XPRESS. MacScience Co. Ltd, Yokohama, Japan.
Michalik, M., Freier, T., Reinke, H. & Peseke, K. (2002). J. Chem. Soc. Perkin Trans. 2, pp. 114-119.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds