Diethyl 2-[(4-nitro­phen­yl)(4-phenyl-1,2,3-selenadiazol-5-yl)meth­yl]malonate

A Marx; S Saravanan; S Muthusubramanian; V Manivannan; Nigam P Rath

doi:10.1107/S160053680800706X

. 2008 Mar 20;64(Pt 4):o729. doi: 10.1107/S160053680800706X

Diethyl 2-[(4-nitrophenyl)(4-phenyl-1,2,3-selenadiazol-5-yl)methyl]malonate

A Marx ^a, S Saravanan ^b, S Muthusubramanian ^b, V Manivannan ^a,^*, Nigam P Rath ^c

PMCID: PMC2961064 PMID: 21202119

Abstract

In the title compound, C₂₂H₂₁N₃O₆Se, the heterocyclic ring makes dihedral angles of 50.03 (11) and 67.75 (11)°, respectively, with the benzene and phenyl rings. The terminal C atoms of the ester groups are disordered over two positions: the site occupancies for the C atoms are 0.62 (3)/0.38 (3) and 0.48 (3)/0.52 (3). In the crystal structure, weak intra- and intermolecular C—H⋯O interactions are observed.

Related literature

For biological activities, see: El-Kashef et al. (1986 ▶); El-Bahaie et al. (1990 ▶). For closely related compounds, see: Bertini et al. (1984 ▶); Gunasekaran et al. (2007 ▶).

Experimental

Crystal data

C₂₂H₂₁N₃O₆Se
M _r = 502.38
Triclinic,
a = 9.9530 (6) Å
b = 10.5220 (6) Å
c = 12.2305 (7) Å
α = 79.350 (3)°
β = 74.632 (3)°
γ = 67.632 (3)°
V = 1137.05 (11) Å³
Z = 2
Mo Kα radiation
μ = 1.69 mm⁻¹
T = 295 (2) K
0.23 × 0.17 × 0.16 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.697, T _max = 0.773
30194 measured reflections
4477 independent reflections
3053 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.161
S = 1.04
4477 reflections
313 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.93 e Å⁻³
Δρ_min = −0.80 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800706X/is2278sup1.cif

e-64-0o729-sup1.cif^{(23KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800706X/is2278Isup2.hkl

e-64-0o729-Isup2.hkl^{(214.9KB, hkl)}

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
C22A—H22D⋯O2ⁱ	0.96	2.47	3.38 (4)	159
C11—H11⋯O6ⁱⁱ	0.93	2.56	3.410 (6)	152
C18—H18A⋯O4	0.97	2.29	2.686 (7)	103
C21—H21C⋯O6	0.97	2.17	2.627 (6)	107

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

supplementary crystallographic information

Comment

Selenium containing compounds like 1,2,3-selenadiazole possess various beneficial activities like antibacterial (El-Kashef et al., 1986), antimicrobial (El-Bahaie et al., 1990) activities. The geometric parameters in the compound, (I) (Fig. 1), agree with the reported values of similar structures (Bertini et al., 1984; Gunasekaran et al., 2007).

The heterocyclic ring makes the dihedral angles of 50.03 (11) and 67.75 (11)° with the benzene and phenyl rings. The terminal C atoms of the ester groups are disordered over two positions; the site occupancies for the C atoms are 0.62/0.38 and 0.48/0.52. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing of (I) is stabilized by weak intermolecular C—H···O contacts (Table 1 and Fig. 2).

Experimental

2.22 g (0.02 mol) of powdered selenium dioxide was dissolved in glacial acetic acid by gentle warming. To this warm solution, 0.002 mol of diethyl 2-{3-[2-(aminocarbonyl)hydrazono]-1-(4-nitrophenyl)-3-phenylpropyl} malonate was added at once and the mixture was gently heated on a water bath until gas evolution ceased. The selenium deposited on cooling was removed by filtration and the filtrate poured into crushed ice, extracted with chloroform and purified by column chromatography, using silica gel (60–120 mesh) to yield diethyl 2-[(4-nitrophenyl) (4-phenyl-1,2,3-selenadiazol-5-yl)methyl]malonate. Solvent used for crystallization is ethanol.