3-(4-Methyl­phen­yl)-1-phenyl-3-(4,5,6,7-tetra­hydro-1,2,3-benzoselenadiazol-4-yl)propan-1-one

J Muthukumaran; M Nishandhini; S Chitra; P Manisankar; Suman Bhattacharya; S Muthusubramanian; R Krishna; J Jeyakanthan

doi:10.1107/S160053681102174X

. 2011 Jun 18;67(Pt 7):o1660–o1661. doi: 10.1107/S160053681102174X

3-(4-Methylphenyl)-1-phenyl-3-(4,5,6,7-tetrahydro-1,2,3-benzoselenadiazol-4-yl)propan-1-one

J Muthukumaran ^a, M Nishandhini ^b, S Chitra ^c, P Manisankar ^c, Suman Bhattacharya ^d, S Muthusubramanian ^e, R Krishna ^a,^‡, J Jeyakanthan ^b,^*

PMCID: PMC3151998 PMID: 21837060

Abstract

In the title compound, C₂₂H₂₂N₂OSe, the fused six-membered ring of the 4,5,6,7-tetrahydrobenzo[d][1,2,3] selenadiazole group adopts a near to envelope (E form) conformation and the five-membered 1,2,3-selenadiazole ring is essentially planar (r.m.s. deviation = 0.0059 Å). In the crystal, adjacent molecules are interlinked through weak intermolecular C—H⋯π interactions.

Related literature

For bond lengths in compounds containing a 1,2,3-selenadiazole group, see: Arsenyan et al. (2007 ▶); Saravanan et al. (2006a ▶,b ▶, 2007 ▶, 2008 ▶); Marx et al. (2007 ▶, 2008a ▶,b ▶); Gunasekaran et al. (2007a ▶,b ▶). For biological applications of 1,2,3-selenadiazole derivatives, see: Kuroda et al. (2001 ▶); El-Bahaie et al. (1990 ▶); El-Kashef et al. (1986 ▶); Plano et al. (2010 ▶); Padmavathi et al. (2002 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For C—H⋯π interactions, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C₂₂H₂₂N₂OSe
M _r = 409.38
Triclinic,
a = 8.1485 (9) Å
b = 9.7929 (9) Å
c = 12.1234 (13) Å
α = 98.707 (9)°
β = 96.387 (9)°
γ = 94.792 (9)°
V = 945.36 (17) Å³
Z = 2
Mo Kα radiation
μ = 2.00 mm⁻¹
T = 293 K
0.5 × 0.40 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.585, T _max = 1.000
8343 measured reflections
3339 independent reflections
2615 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.100
S = 1.00
3339 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S160053681102174X/zl2374sup1.cif

e-67-o1660-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102174X/zl2374Isup2.hkl

e-67-o1660-Isup2.hkl^{(163.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681102174X/zl2374Isup3.cml

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

Acknowledgments

JJ thanks Dr Binoy Krishna Saha, Assistant Professor, Department of Chemistry, Pondicherry University, Puducherry, for providing access to the X-ray facility. JM thanks the Council for Scientific and Industrial Research (CSIR) for a Senior Research Fellowship (SRF).

supplementary crystallographic information

Comment

1,2,3-Selenadiazole and its derivatives exhibit various potential biological activities 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. Considering the importances of the 1,2,3-selenadiazole derivatives, we present herein the single-crystal structure analysis of the title compound. The bond lengths of the 1,2,3-selenadiazole moiety in the title compound are comparable to those observed for selenadiazole moieties in several crystal structures such as 4-methyl-5-ethoxycarbonyl-1,2,3-selenadiazole phenylboronic acid (Arsenyan et al., 2007), diethyl 2-((4-methylphenyl)(4-phenyl-1,2,3-selenadiazol-5-yl)methyl)malonate (Saravanan et al., 2006a), 4-(4-chlorophenyl)-5-(1-(4-methoxyphenyl)-2-methyl-2-nitropropyl)-1,2,3-selenadiazole (Saravanan et al., 2006b), 3-(4-methylphenyl)-3-(4-(4-methylphenyl)-1,2,3-selenadiazol-5-yl)-2-phenylpropanenitrile (Saravanan et al., 2007), ethyl (Z)-3-(4-chlorophenyl)-2-cyano-3-(4-phenyl-1,2,3-selenadiazol-5-yl)prop-2-enoate (Saravanan et al., 2008), 5-(2-methyl-2-nitro-1-phenylpropyl)-4-phenyl-1,2,3-selenadiazole (Marx et al., 2007), 4-(4-Chlorophenyl)-5-(1-(4-chlorophenyl)-2-methyl-2-nitropropyl)-1,2,3-selenadiazole (Marx et al., 2008a), diethyl 2-((4-nitrophenyl)(4-phenyl-1,2,3-selenadiazol-5-yl)methyl)malonate (Marx et al., 2008b), 5-[2-methyl-1-(4-methylphenyl)-2-nitropropyl]-4-phenyl-1,2,3-selenadiazole (Gunasekaran et al., 2007a) and 4-(4-chlorophenyl)-5-[2-methyl-1-(4-methylphenyl)-2-nitropropyl]-1,2,3-selenadiazole (Gunasekaran et al., 2007b). The molecular structure of the title compound is shown in Fig. 1.

The five-membered 1,2,3-selenadiazole moiety (C1/N1/N2/Se1/C2) of the title compound adopts a planar conformation as observed in the selenadiazole moieties of several crystal structures (Arsenyan et al., 2007; Saravanan et al., 2006a; Saravanan et al., 2006b; Saravanan et al., 2007; Saravanan et al., 2008; Marx et al., 2007; Marx et al., 2008a; Marx et al., 2008b; Gunasekaran et al., 2007a; Gunasekaran et al., 2007b). Cremer & Pople puckering analysis (Cremer & Pople, 1975) cannot be performed, for its weighted average absolute torsion angle is 0.89°, which is less than 5.0°. However, the fused six-membered ring (C1/C2/C3/C4/C5/C6) of the 4,5,6,7-tetrahydrobenzo[d][1,2,3] selenadiazole group adopts a near envelope (E form) conformation with puckering parameters of Q = 0.485 (3) Å, θ = 47.7 (4)° and Φ = 217.1 (5)°.

The molecular structure is stabilized by an intramolecular C7—H7···N1 interaction (Fig. 2) [C7-N1 distance: 2.96 Å, H7-N1 distance: 2.57 Å and C7-H7···N1 angle 104 °]. The C—H···π interaction (Fig. 2) is observed between C4—H4A···Cg (Cg is the centroid of the C17—C22 six-membered ring, C···Cg distance: 3.549 (3) Å, H-Perp: -2.61 Å), which contributes to the stabilization of crystal packing (Fig. 3, symmetry code for the centroid: 1-x,-y,-z). The bond distance of C—H···π interaction agrees with those described by Desiraju & Steiner (1999).

Experimental

A mixture of 2-[1-(4-methylphenyl)-3-oxo-3-phenylpropyl]-1-cyclohexanone (1 mmol, 0.32 g) and semicarbazide hydrochloride (1 mmol, 0.11 g) in ethanol (10 ml) was refluxed for 3 h. After completion of the reaction as monitored by TLC, the mixture was poured into ice cold water (50 ml) and the resulting mono-semicarbazone solid was filtered off. Then, a mixture of mono-semicarbazone (1 mmol, 0.38 g) and SeO₂ (2 mmol, 0.44 g) in tetrahydrofuran (THF) (10 ml) were refluxed on a water bath for 30 minutes. After completion of the reaction as monitored by TLC, the reaction mixture was filtered to remove selenium powder, the filtrate was concentrated under vacuum, and the residue was subjected to column chromatography using a petroleum ether/ethylacetate mixture (95:5; v/v) as eluent to afford the pure product (Yield: 69%, melting point: 398-399 K). Dissolving the pure compound in a 3:1 mixture of dichloromethane:ethylacetate and slow evaporation of the solvents provided crystals suitable for X-ray analysis. Spectroscopic data for the title compound: IR (KBr): 2940 (C-H), 1679 (C=O), 1585 (N=N), 1351 (C-N)cm^-1 .