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Volume 69 
Part 3 
Page o430  
March 2013  

Received 29 November 2012
Accepted 18 February 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.031
wR = 0.083
Data-to-parameter ratio = 20.0
Details
Open access

5-[1-(4-Methylphenyl)-2-nitrobutyl]-4-phenyl-1,2,3-selenadiazole

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India,bDepartment of Chemistry, Sri Sarada College for Women (Autonomus), Fairlands, Salem 636 016, India, and cDepartment of Industrial Chemistry, Alagappa University, Karaikudi 630 003, India
Correspondence e-mail: mnpsy2004@yahoo.com

In the title compound, C19H19N3O2Se, the selenadiazole ring is roughly planar [maximum deviation 0.033 (6) Å]. The attached phenyl ring is twisted away at an angle of 47.5 (1)°. The butyl group is in an extended conformation [C-C-C-C torsion angle = 174.7 (2)°]. In the crystal, C-H...O interactions form C(10) chains running aling the c-axis direction.

Related literature

For general background to selenadiazol derivatives, see: El-Bahaie et al. (1990[El-Bahaie, S., Assy, M. G. & Hassanien, M. M. (1990). Pharmazie, 45, 791-793.]); El-Kashef et al. (1986[El-Kashef, H. S., E-Bayoumy, B. & Aly, T. I. (1986). Egypt. J. Pharm. Sci. 27, 27-30.]); Kuroda et al. (2001[Kuroda, K., Uchikurohane, T., Tajima, S. & Tsubata, K. (2001). US Patent 6166054.]); Khanna (2005[Khanna, P. K. (2005). Phosphorus Sulfur Silicon Relat. Elem. 180, 951-955.]); Padmavathi et al. (2002[Padmavathi, V., Sumathi, R. P. & Padmaja, A. (2002). J. Ecobiol. 14, 9-12.]); Plano et al. (2010[Plano, D., Moreno, E., Font, M., Encio, I., Palop, J. A. & Sanmartin, C. (2010). Arch. Pharm. Chem. Life Sci. 10, 680-691.]); Stadtman (1991[Stadtman, T. C. (1991). J. Biol. Chem. 266, 16257-16260.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. 1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C19H19N3O2Se

  • Mr = 400.33

  • Triclinic, [P \overline 1]

  • a = 8.2088 (5) Å

  • b = 8.4755 (5) Å

  • c = 13.7031 (8) Å

  • [alpha] = 80.669 (3)°

  • [beta] = 81.832 (3)°

  • [gamma] = 76.681 (3)°

  • V = 910.00 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.08 mm-1

  • T = 293 K

  • 0.22 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART APEX CCD detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.639, Tmax = 0.688

  • 16036 measured reflections

  • 4516 independent reflections

  • 3581 reflections with I > 2[sigma](I)

  • Rint = 0.029

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

  • wR(F2) = 0.083

  • S = 1.04

  • 4516 reflections

  • 226 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C19-H19C...O2i 0.96 2.52 3.414 (3) 155
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6877 ).


Acknowledgements

The authors thank the TBI consultancy, University of Madras, India, for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. 1-19.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Bahaie, S., Assy, M. G. & Hassanien, M. M. (1990). Pharmazie, 45, 791-793.  [ChemPort] [PubMed]
El-Kashef, H. S., E-Bayoumy, B. & Aly, T. I. (1986). Egypt. J. Pharm. Sci. 27, 27-30.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Khanna, P. K. (2005). Phosphorus Sulfur Silicon Relat. Elem. 180, 951-955.  [CrossRef] [ChemPort]
Kuroda, K., Uchikurohane, T., Tajima, S. & Tsubata, K. (2001). US Patent 6166054.
Padmavathi, V., Sumathi, R. P. & Padmaja, A. (2002). J. Ecobiol. 14, 9-12.  [ChemPort]
Plano, D., Moreno, E., Font, M., Encio, I., Palop, J. A. & Sanmartin, C. (2010). Arch. Pharm. Chem. Life Sci. 10, 680-691.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stadtman, T. C. (1991). J. Biol. Chem. 266, 16257-16260.  [PubMed] [ChemPort]


Acta Cryst (2013). E69, o430  [ doi:10.1107/S1600536813004662 ]

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