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

Sugumar, P.; Sankari, S.; Manisankar, P.; Ponnuswamy, M.N.

doi:10.1107/S1600536813004662

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 (C-C) = 0.003 Å
R = 0.031
wR = 0.083
Data-to-parameter ratio = 20.0
Details

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

P. Sugumar,^a S. Sankari,^b P. Manisankar ^c and M. N. Ponnuswamy ^a ^*

^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-HO 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-Kashef et al. (1986); Kuroda et al. (2001); Khanna (2005); Padmavathi et al. (2002); Plano et al. (2010); Stadtman (1991). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₉H₁₉N₃O₂Se
M_r = 400.33
Triclinic, $[P \overline 1]$
a = 8.2088 (5) Å
b = 8.4755 (5) Å
c = 13.7031 (8) Å
= 80.669 (3)°
= 81.832 (3)°
= 76.681 (3)°
V = 910.00 (9) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.639, T_max = 0.688
16036 measured reflections
4516 independent reflections
3581 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.083
S = 1.04
4516 reflections
226 parameters
H-atom parameters constrained
_max = 0.37 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C19-H19CO2ⁱ	0.96	2.52	3.414 (3)	155
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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.
El-Kashef, H. S., E-Bayoumy, B. & Aly, T. I. (1986). Egypt. J. Pharm. Sci. 27, 27-30.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Khanna, P. K. (2005). Phosphorus Sulfur Silicon Relat. Elem. 180, 951-955.
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.
Plano, D., Moreno, E., Font, M., Encio, I., Palop, J. A. & Sanmartin, C. (2010). Arch. Pharm. Chem. Life Sci. 10, 680-691.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stadtman, T. C. (1991). J. Biol. Chem. 266, 16257-16260.

organic compounds