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Volume 66 
Part 10 
Page o2631  
October 2010  

Received 8 September 2010
Accepted 17 September 2010
Online 25 September 2010

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.043
wR = 0.128
Data-to-parameter ratio = 14.6
Details
Open access

2-(1,3-Dioxoisoindolin-2-yl)acetonitrile

Younas Aouine,a Anouar Alami,a* Abdelilah El Hallaoui,a Abdelrhani Elachqara and Hafid Zouihrib

aLaboratoire de Chimie Organique, Faculté des Sciences, Dhar el Mahraz, Université Sidi Mohammed Ben Abdellah, Fès, Morocco, and bLaboratoires de Diffraction des Rayons X, Division UATRS, Centre National pour la Recherche Scientifique et Technique, Rabat, Morocco
Correspondence e-mail: alamianouar@yahoo.fr

The asymmetric unit of the title compound, C10H6N2O2, contains two independent molecules. The dihedral angles between the acetonitrile and the 1H-isoindole-1,3(2H)-dione units are 69.0 (7)° and 77.0 (5)° in the two molecules. One of the two terminal N atoms is disordered over two positions in a 0.66 (8):0,34 (8) ratio. In the crystal structure, the molecules are linked by intermolecular C-H...O hydrogen bonds.

Related literature

The title compound was prepared as a key intermediate for the synthesis of a new new tetrazolic derivative. For the use of tetrazoles as pesticides, see: Schocken et al. (1989[Schocken, M. J., Creekmore, R. W., Theodoridis, G., Nystrom, G. J. & Robinson, R. A. (1989). Appl. Environ. Microbiol. 55, 1220-2122.]); Yanagi et al. (2001[Yanagi, A. (2001). Pflanzenschutz Nachr. Bayer. 54, 1-11.]); Lim et al. (2007[Lim, S. J., Sunohara, Y. & Matsumoto, H. (2007). J. Pestic. Sci. 32, 249-254.]) and as antihypertensive, antialergic, antibiotic and anticonvulsant agents, see: Hashimoto et al. (1998[Hashimoto, Y., Ohashi, R., Kurosawa, Y., Minami, K., Kaji, H., Hayashida, K., Narita, H. & Murata, S. (1998). J. Cardiovasc. Pharm. 31, 568-575.]); Berghmans et al. (2007[Berghmans, S., Hunt, J., Roach, A. & Goldsmith, P. (2007). Epilepsy Res. 75, 18-28.]). For their use in cancer, AIDS and obesity treatments, see: Tamura et al. (1998[Tamura, Y. F., Watanabe, F., Nakatani, T., Yasui, K., Fuji, M., Komurasaki, T., Tsuzuki, H., Maekawa, R., Yoshioka, T., Kawada, K., Sugita, K. & Ohtani, M. (1998). J. Med. Chem. 41, 640-649.]); Shih et al. (1999[Shih, T. L., Candelore, M. R., Cascieri, M. A., Chiu, S.-H. L., Colwell, L. F. Jr, Deng, L., Feeney, W. P., Forrest, M. J., Hom, G. J., MacIntyre, D. E., Miller, R. R., Stearns, R. A., Strader, C. D., Tota, L., Wyvratt, M. J., Fisher, M. H. & Weber, A. E. (1999). Bioorg. Med. Chem. Lett. 9, 1251-1254.]); Muraglia et al. (2006[Muraglia, E., Kinzel, O. D., Laufer, R., Miller, M. D., Moyer, G., Munshi, V., Orvieto, F., Palumbi, M. C., Pescatore, G., Rowley, M., Williams, P. D. & Summa, V. (2006). Bioorg. Med. Chem. Lett. 16, 2748-2752.]). A major advantage of tetrazoles over carboxylic acids is that they are resistant to many biological metabolic degradation pathways, see: Singh et al. (1980[Singh, H., Chawla, A. S., Kapoor, V. K., Paul, D. & Malhotra, R. K. (1980). Prog. Med. Chem. 17, 151-183.]).

[Scheme 1]

Experimental

Crystal data

  • C10H6N2O2

  • Mr = 186.17

  • Triclinic, [P \overline 1]

  • a = 8.0960 (2) Å

  • b = 8.4371 (2) Å

  • c = 14.3118 (3) Å

  • [alpha] = 85.072 (1)°

  • [beta] = 79.272 (1)°

  • [gamma] = 68.421 (1)°

  • V = 893.02 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.25 × 0.24 × 0.16 mm
Data collection

  • Bruker APEXII CCD detector diffractometer

  • 18332 measured reflections

  • 3906 independent reflections

  • 2885 reflections with I > 2[sigma](I)

  • Rint = 0.034
Refinement

  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.128

  • S = 1.05

  • 3906 reflections

  • 267 parameters

  • 6 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 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
C13-H13...O12i 0.93 2.51 3.386 (2) 158
C15-H15...O20ii 0.93 2.45 3.144 (2) 132
C18-H18B...O20 0.97 2.42 3.372 (2) 167
C28-H28A...O21iii 0.97 2.39 3.298 (2) 156
Symmetry codes: (i) x, y-1, z; (ii) -x+2, -y+1, -z; (iii) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2206 ).

Acknowledgements

The authors thank the CNRST, Morocco, for making this work possible.

References

Berghmans, S., Hunt, J., Roach, A. & Goldsmith, P. (2007). Epilepsy Res. 75, 18-28.  [CrossRef] [PubMed] [ChemPort]
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Hashimoto, Y., Ohashi, R., Kurosawa, Y., Minami, K., Kaji, H., Hayashida, K., Narita, H. & Murata, S. (1998). J. Cardiovasc. Pharm. 31, 568-575.  [CrossRef] [ChemPort]
Lim, S. J., Sunohara, Y. & Matsumoto, H. (2007). J. Pestic. Sci. 32, 249-254.  [CrossRef] [ChemPort]
Muraglia, E., Kinzel, O. D., Laufer, R., Miller, M. D., Moyer, G., Munshi, V., Orvieto, F., Palumbi, M. C., Pescatore, G., Rowley, M., Williams, P. D. & Summa, V. (2006). Bioorg. Med. Chem. Lett. 16, 2748-2752.  [CrossRef] [PubMed] [ChemPort]
Schocken, M. J., Creekmore, R. W., Theodoridis, G., Nystrom, G. J. & Robinson, R. A. (1989). Appl. Environ. Microbiol. 55, 1220-2122.  [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shih, T. L., Candelore, M. R., Cascieri, M. A., Chiu, S.-H. L., Colwell, L. F. Jr, Deng, L., Feeney, W. P., Forrest, M. J., Hom, G. J., MacIntyre, D. E., Miller, R. R., Stearns, R. A., Strader, C. D., Tota, L., Wyvratt, M. J., Fisher, M. H. & Weber, A. E. (1999). Bioorg. Med. Chem. Lett. 9, 1251-1254.  [CrossRef] [PubMed]
Singh, H., Chawla, A. S., Kapoor, V. K., Paul, D. & Malhotra, R. K. (1980). Prog. Med. Chem. 17, 151-183.  [CrossRef] [ChemPort] [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Tamura, Y. F., Watanabe, F., Nakatani, T., Yasui, K., Fuji, M., Komurasaki, T., Tsuzuki, H., Maekawa, R., Yoshioka, T., Kawada, K., Sugita, K. & Ohtani, M. (1998). J. Med. Chem. 41, 640-649.  [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Yanagi, A. (2001). Pflanzenschutz Nachr. Bayer. 54, 1-11.

Acta Cryst (2010). E66, o2631  [ doi:10.1107/S1600536810037335 ]

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