Ethyl 3-(4-meth­oxy­phen­yl)-2-phenyl-3-(4-phenyl-1,2,3-selenadiazol-5-yl)propano­ate

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

doi:10.1107/S1600536812028322

. 2012 Jul 7;68(Pt 8):o2347. doi: 10.1107/S1600536812028322

Ethyl 3-(4-methoxyphenyl)-2-phenyl-3-(4-phenyl-1,2,3-selenadiazol-5-yl)propanoate

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

PMCID: PMC3414282 PMID: 22904815

Abstract

In the title compound, C₂₆H₂₄N₂O₃Se, the selenadiazole ring is planar [maximum deviation = 0.002 (2) Å]. The dihedral angle between the selenadiazole ring and the attached phenyl ring is 49.00 (13)°. The crystal structure is stabilized by intermolecular C—H⋯N and C—H⋯π interactions.

Related literature

For general background to selenadiazole derivatives, see: El-Bahaie et al. (1990 ▶); El-Kashef et al. (1986 ▶); Kuroda et al. (2001 ▶); Padmavathi et al. (2002 ▶); Plano et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₆H₂₄N₂O₃Se
M _r = 491.43
Monoclinic,
a = 11.8187 (4) Å
b = 12.8241 (5) Å
c = 16.1837 (6) Å
β = 105.280 (2)°
V = 2366.16 (15) Å³
Z = 4
Mo Kα radiation
μ = 1.62 mm⁻¹
T = 293 K
0.20 × 0.15 × 0.15 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.748, T _max = 0.785
22954 measured reflections
5918 independent reflections
3015 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.108
S = 0.99
5918 reflections
291 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.28 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/S1600536812028322/bt5929sup1.cif

e-68-o2347-sup1.cif^{(29.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028322/bt5929Isup2.hkl

e-68-o2347-Isup2.hkl^{(283.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812028322/bt5929Isup3.cml

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

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

Cg3 and Cg4 are the centroids of the C10–C15 and C17–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯N1ⁱ	0.93	2.57	3.420 (3)	152
C12—H12⋯Cg4ⁱⁱ	0.96	2.81	3.673 (3)	154
C24—H24A⋯Cg3ⁱⁱⁱ	0.96	2.80	3.580 (3)	138

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

Selenium containing compounds, like 1,2,3-selenadiazoles are of increasing interest because of 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) activities. In view of the growing importance 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 selenadiazol ring is planar(maximum deviation -0.002 (2) Å). The dihedral angle between the selenadiazol ring and the attached phenyl ring(C2—C7) is 49.00 (13)°. The propanoate group assumes an extended conformation which can be seen from the torsion angle (C16—C23—O1—C24) value of 178.4 (2)°. The methoxy group lies in the plane of the phenyl ring (C10—C15) and twisted away with propanate group & phenyl ring (C17—C22) at angles of 8.21 (12)° & 68.11 (12)°, respectively. The packing of the molecules viewed down a axis is shown in Fig. 2. The molecules are stabilized by C—H···N and C—H···π types of intermolecular interactions in addition to van der Waals forces.

Experimental

A mixture of ethyl-3-(4-methoxyphenyl)-5-oxo-2,5-diphenylpentanoate (1 mmol), semicarbazide hydrochloride(2 mmol) and anhydrous sodium acetate (3 mmol) in ethanol (10 ml) was refluxed for 4 hrs. 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 mixtureof 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 ethyl 3-(4,5-dihydro-4-phenyl-1,2, 3-selenadiazol-5-yl)-3-(4-methoxyphenyl)-2-phenylpropanoate.