5-(2-Nitro-1-phenyl­but­yl)-4-phenyl-1,2,3-selenadiazole

S Sankari; P Sugumar; P Manisankar; S Muthusubramanian; M N Ponnuswamy

doi:10.1107/S1600536812007027

. 2012 Feb 29;68(Pt 3):o871. doi: 10.1107/S1600536812007027

5-(2-Nitro-1-phenylbutyl)-4-phenyl-1,2,3-selenadiazole

S Sankari ^a, P Sugumar ^b, P Manisankar ^c, S Muthusubramanian ^d, M N Ponnuswamy ^b,^*

PMCID: PMC3297921 PMID: 22412724

Abstract

In the title compound, C₁₈H₁₇N₃O₂Se, the selenadiazole ring is planar [maximum deviation = 0.012 (2) Å for the ring C atom bearing the phenyl substituent]. The dihedral angle between the selenadiazole ring and the attached benzene ring is 46.5 (1)°. There is one short intramolecular C—H⋯Se contact.

Related literature

For general background to selenadiazole 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 ▶).

Experimental

Crystal data

C₁₈H₁₇N₃O₂Se
M _r = 386.31
Triclinic,
a = 7.879 (5) Å
b = 8.450 (5) Å
c = 13.438 (5) Å
α = 80.629 (5)°
β = 85.273 (5)°
γ = 75.352 (5)°
V = 853.2 (8) Å³
Z = 2
Mo Kα radiation
μ = 2.22 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.636, T _max = 0.702
15132 measured reflections
4265 independent reflections
3478 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.079
S = 1.05
4265 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812007027/bt5784sup1.cif

e-68-0o871-sup1.cif^{(19.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007027/bt5784Isup2.hkl

e-68-0o871-Isup2.hkl^{(204.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812007027/bt5784Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯Se1	0.98	2.85	3.313 (3)	110

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Acknowledgments

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

supplementary crystallographic information

Comment

Selenadiazoles, having one selenium and two nitrogen atoms in a five membered ring, are the important class of organoselenium compounds utilized in the synthesis of semiconductor nanoparticles (Khanna, 2005). These 1,2, 3-selenadiazoles are used as the synthetic intermediates in the preparation of many alkynes and other selenium compounds. In addition, 1,2,3-Selenadiazoles are of interest owing to their chemical properties and biological applications such as anti-fungal (Kuroda et al., 2001), anti-bacterial (El-Kashef et al., 1986), anti-microbial (El-Bahaie et al., 1990), anti-cancer (Plano et al., 2010) and insecticidal (Padmavathi et al., 2002) properties. Glutathione peroxidases(GPx) are the antioxidant selenoenzymes protecting various organisms from oxidative stress by catalyzing the reduction of hydroperoxides at the expense of glutathione(GSH) (Stadtman, 1991). Owing to the above mentioned important properties of selenium containing compounds, the crystal structure of the title compound has been carried out.

The ORTEP plot of the molecule is shown in Fig.1. The bond lengths [Se1—N1] 1.877 (2)Å and [Se1—C8] 1.839 (2)Å are normal. The selenadiazol ring is planar and oriented at an angle of 46.5 (1)° with the attached phenyl ring. The phenylbutyl group is in extended conformation, which can be seen from the torsion angle values of [C9—C16—C17—C18]-178.5 (2)° & [C10—C9—C16—C17]-168.8 (2)°. The planar nitro group is oriented at an angle of 78.9 (2)° with phenylbutyl group. The molecular packing is controlled by C—H···π type of intermolecular interactions in addition to van der Waals forces.

Experimental

A mixture of 4-nitro-1,3-diiphenylhexan-1-one (1 mmol), semicarbazide hydrochloride(2 mmol) and anhydrous sodium acetate (3 mmol) in ethanol (10 ml) was refluxed for 4 h. After completion of the reaction as monitored by TLC, the mixture was poured into ice cold water and the resulting semicarbazone was filtered off. Then, a mixture of semicarbazone (1 mmol) and SeO2 (2 mmol) in tetrahydrofuran (10 ml) were refluxed on a water bath for 1 h. The selenium deposited on cooling was removed by filtration, and the filtrate was poured into crushed ice, extracted with dichloromethane, and purified by column chromatography using silica gel (60–120 mesh) with 97:3 petroleum ether: ethyl acetate as eluent to give 5-(2-nitro-1-phenylbutyl)-4-phenyl-1,2, 3-selenadiazole.