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Volume 68 
Part 5 
Page o1381  
May 2012  

Received 23 March 2012
Accepted 29 March 2012
Online 13 April 2012

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.027
wR = 0.068
Data-to-parameter ratio = 22.8
Details
Open access

1-Methyl-2,3-dihydro-1H-benzimidazole-2-selone

Gunay Z. Mammadova,a* Zhanna V. Matsulevich,b Vladimir K. Osmanov,b Alexander V. Borisovb and Victor N. Khrustalevc

aBaku State University, Z. Khalilov St 23, Baku AZ-1148, Azerbaijan,bR.E. Alekseev Nizhny Novgorod State Technical University, 24 Minin St, Nizhny Novgorod, 603950, Russian Federation, and cX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St, B-334, Moscow 119991, Russian Federation
Correspondence e-mail: gunka479@mail.ru

The title compound C8H8N2Se, is the product of the reaction of 2-chloro-1-methylbenzimidazole with sodium hydroselenide. The molecule is almost planar (r.m.s. deviation = 0.041 Å) owing to the presence of the long chain of conjugated bonds (Se=C-NMe-C=C-C=C-C=C-NH). The C=Se bond length [1.838 (2) Å] corresponds well to those found in the close analogs and indicates its pronounced double-bond character. In the crystal, molecules form helicoidal chains along the b axis by means of N-H...Se hydrogen bonds.

Related literature

For selones as potential antithyroid drugs, see: Taurog et al. (1994[Taurog, A., Dorris, M. L., Guziec, L. J. & Guziec, F. S. (1994). Biochem. Pharmacol. 48, 1447-1453.]); Roy & Mugesh (2005[Roy, G. & Mugesh, G. (2005). J. Am. Chem. Soc. 127, 15207-15217.], 2006[Roy, G. & Mugesh, G. (2006). Bioorg. Chem. Appl. pp. 1-9.]); Roy et al. (2007[Roy, G., Das, D. & Mugesh, G. (2007). Inorg. Chim. Acta, 360, 303-316.], 2011[Roy, G., Bhabak, K. P. & Mugesh, G. (2011). Cryst. Growth Des. 11, 2279-2286.]). For related compounds, see: Guziec & Guziec (1994[Guziec, L. J. & Guziec, F. S. (1994). J. Org. Chem. 59, 4691-4692.]); Husebye et al. (1997[Husebye, S., Lindeman, S. V. & Rudd, M. D. (1997). Acta Cryst. C53, 809-811.]); Aydin et al. (1999[Aydin, A., Soylu, H., Küçükbay, H., Akkurt, M. & Ercan, F. (1999). Z. Kristallogr. New Cryst. Struct. 214, 295-296.]); Akkurt et al. (2004[Akkurt, M., Öztürk, S., Küçükbay, H., Orhan, E. & Büyükgüngör, O. (2004). Acta Cryst. E60, o1263-o1265.], 2011[Akkurt, M., Yilmaz, Ü., Küçükbay, H. & Büyükgüngör, O. (2011). Acta Cryst. E67, o1179.]); Landry et al. (2006[Landry, V. K., Minoura, M., Pang, K., Buccella, D., Kelly, B. V. & Parkin, G. (2006). J. Am. Chem. Soc. 128, 12490-12497.]); Nakanishi et al. (2008[Nakanishi, W., Hayashi, S., Morinaka, S., Sasamori, T. & Tokitoh, N. (2008). New J. Chem. 32, 1881-1889.]); Mammadova et al. (2011[Mammadova, G. Z., Matsulevich, Z. V., Osmanov, V. K., Borisov, A. V. & Khrustalev, V. N. (2011). Acta Cryst. E67, o3050.]). For hypervalent adducts of selones with dihalogens and interhalogens, see: Aragoni et al. (2001[Aragoni, M. C., Arca, M., Demartin, F., Devillanova, F. A., Garau, A., Isaia, F., Lelj, F., Lippolis, V. & Verani, G. (2001). Chem. Eur. J. 7, 3122-3133.]); Boyle & Godfrey (2001[Boyle, P. D. & Godfrey, S. M. (2001). Coord. Chem. Rev. 223, 265-299.]); Roy et al. (2011[Roy, G., Bhabak, K. P. & Mugesh, G. (2011). Cryst. Growth Des. 11, 2279-2286.]).

[Scheme 1]

Experimental

Crystal data

  • C8H8N2Se

  • Mr = 211.12

  • Monoclinic, P 21 /n

  • a = 9.9434 (13) Å

  • b = 5.8472 (8) Å

  • c = 13.6387 (18) Å

  • [beta] = 95.360 (2)°

  • V = 789.50 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.69 mm-1

  • T = 100 K

  • 0.24 × 0.20 × 0.20 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.399, Tmax = 0.454

  • 9470 measured reflections

  • 2304 independent reflections

  • 1941 reflections with I > 2[sigma](I)

  • Rint = 0.030
Refinement

  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.068

  • S = 1.00

  • 2304 reflections

  • 101 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.10 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3N...Se1i 0.91 2.58 3.471 (2) 168
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2347 ).

Acknowledgements

We thank Professor Abel M. Maharramov for fruitful discussions and help in this work.

References

Akkurt, M., Öztürk, S., Küçükbay, H., Orhan, E. & Büyükgüngör, O. (2004). Acta Cryst. E60, o1263-o1265.  [CSD] [CrossRef] [details]
Akkurt, M., Yilmaz, Ü., Küçükbay, H. & Büyükgüngör, O. (2011). Acta Cryst. E67, o1179.  [CSD] [CrossRef] [details]
Aragoni, M. C., Arca, M., Demartin, F., Devillanova, F. A., Garau, A., Isaia, F., Lelj, F., Lippolis, V. & Verani, G. (2001). Chem. Eur. J. 7, 3122-3133.  [CrossRef] [PubMed] [ChemPort]
Aydin, A., Soylu, H., Küçükbay, H., Akkurt, M. & Ercan, F. (1999). Z. Kristallogr. New Cryst. Struct. 214, 295-296.  [ChemPort]
Boyle, P. D. & Godfrey, S. M. (2001). Coord. Chem. Rev. 223, 265-299.  [ISI] [CrossRef] [ChemPort]
Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Guziec, L. J. & Guziec, F. S. (1994). J. Org. Chem. 59, 4691-4692.  [CrossRef] [ChemPort]
Husebye, S., Lindeman, S. V. & Rudd, M. D. (1997). Acta Cryst. C53, 809-811.  [CrossRef] [details]
Landry, V. K., Minoura, M., Pang, K., Buccella, D., Kelly, B. V. & Parkin, G. (2006). J. Am. Chem. Soc. 128, 12490-12497.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Mammadova, G. Z., Matsulevich, Z. V., Osmanov, V. K., Borisov, A. V. & Khrustalev, V. N. (2011). Acta Cryst. E67, o3050.  [CSD] [CrossRef] [details]
Nakanishi, W., Hayashi, S., Morinaka, S., Sasamori, T. & Tokitoh, N. (2008). New J. Chem. 32, 1881-1889.  [ISI] [CSD] [CrossRef] [ChemPort]
Roy, G., Bhabak, K. P. & Mugesh, G. (2011). Cryst. Growth Des. 11, 2279-2286.  [CrossRef] [ChemPort]
Roy, G., Das, D. & Mugesh, G. (2007). Inorg. Chim. Acta, 360, 303-316.  [ISI] [CSD] [CrossRef] [ChemPort]
Roy, G. & Mugesh, G. (2005). J. Am. Chem. Soc. 127, 15207-15217.  [ISI] [CrossRef] [PubMed] [ChemPort]
Roy, G. & Mugesh, G. (2006). Bioorg. Chem. Appl. pp. 1-9.
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Taurog, A., Dorris, M. L., Guziec, L. J. & Guziec, F. S. (1994). Biochem. Pharmacol. 48, 1447-1453.  [CrossRef] [ChemPort] [PubMed] [ISI]

Acta Cryst (2012). E68, o1381  [ doi:10.1107/S1600536812013700 ]

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