4-Decyl­phenyl 4-benz­yloxy-3-methyl­benzoate

H K Arun Kashi; B S Palakshamurthy; M VinduVahini; H T Srinivasa; H C Devarajegowda

doi:10.1107/S1600536810028965

. 2010 Jul 24;66(Pt 8):o2126. doi: 10.1107/S1600536810028965

4-Decylphenyl 4-benzyloxy-3-methylbenzoate

H K Arun Kashi ^a, B S Palakshamurthy ^a, M VinduVahini ^b, H T Srinivasa ^c, H C Devarajegowda ^a,^*

PMCID: PMC3007531 PMID: 21588415

Abstract

In the title compound, C₃₁H₃₈O₃, the central benzene ring makes dihedral angles of 66.06 (9) and 65.21 (8)°, respectively, with the benzyl and 4-decylphenyl rings.

Related literature

For general background to benzyloxybenzoate, see: Laschat (2009 ▶); Meter & Klanderman (1973 ▶); Young et al. (1974 ▶); Tinn et al. (1982 ▶). For the synthesis, see: Sadashiva & Subba (1975 ▶); Sadashiva (1979 ▶); Hari et al. (2009 ▶). For related structures, see: Blake et al. (1996 ▶); Chin & Goodby (1986 ▶).

Experimental

Crystal data

C₃₁H₃₈O₃
M _r = 458.61
Triclinic,
a = 9.3684 (16) Å
b = 11.168 (2) Å
c = 15.204 (3) Å
α = 68.588 (11)°
β = 87.274 (11)°
γ = 65.578 (10)°
V = 1338.3 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 K
0.22 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: ψ scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.987, T _max = 0.992
23986 measured reflections
6737 independent reflections
3840 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.183
S = 1.04
6737 reflections
308 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810028965/gw2084sup1.cif

e-66-o2126-sup1.cif^{(25.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028965/gw2084Isup2.hkl

e-66-o2126-Isup2.hkl^{(323KB, hkl)}

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

Acknowledgments

The authors thank Dr Gunasekaran and Dr Karthik, Department of Crystallography and Bio-Chemistry, University of Madras Guindy Campus, Chennai, India, for their help with the data collection.

supplementary crystallographic information

Comment

Liquid crystals are unique functional soft materials that possess both order and mobility at the molecular and supramolecular level.One of the major issues in liquid crystal research today is still the poor knowledge of structure-property relationships and thus the synthesis of whole series of structurally related compounds is required in order to allow the design of liquid crystalline and other physical properties (Laschat, 2009) Several benzyloxy derivative liquid crystals were reported with terminal alkyl and alkoxy chains (Meter et al., 1973), and these compounds were shown to be of nematic mesophases (Young et al., 1974; Tinn et al., 1982). Terminal carbonitrile group containing liquid crystals were also synthesized and studied for their positive dielectric anisotropy (Sadashiva et al., 1975; Sadashiva, 1979). In our study a novel rod shaped liquid crystal having a decyloxy chain has been synthesized and characterized using single-crystal X-ray diffraction study. 4-decylphenyl 4-(benzyloxy)-3- methylbenzoate is the study compound showing monotropic nematic mesophase at 305 K.

The structure of decylphenyl 4-(benzyloxy) -3-methylbenzoate contains one independent molecule in the asymmetric unit. The ring systems and alkyl chain are non coplanar with each other. The dihedral angle between the aromatic rings A–B, B–C and A–C are 66.06 (9)°, 65.21 (8)° and 12.89 (10)° respectively. The alkyl chain and ring C together makes a dihedral angle of 10.73 (12)°. The packing of the molecules is stabilized by C7—H7B···O2 hydrogen bond and Van der Waal's forces(Figure 2).

Experimental

A mixture of 3-methyl-4-benzyloxybenzoic acid(0.41 mol) and 4-decylphenol(0.41 mol), a catalytic quantity of 4-(N,N-Dimethylamino) pyridine (DMAP) and dry dichloromethane(10 ml) were stirred for 10 min. To this N, N'-dicyclohexylcarbodiimide(DCC,0.49 mol) was added and the mixture stirred overnight at room temperature. The precipitated N,N'-dicyclohexylurea was filtered off; the filterate was diluted with dichloromethane(30 ml) and washed successively with 5% acetic acid(10 ml x 2), 5% ice-cold sodium hydroxide solution(10 ml x 2) and water(20 ml x 3), then dried over anhydrous sodium sulfate.Removal of solvent gave a product which was chromatographed on silica gel using dichloromethane as eluent. Removal of solvent from the eluate afforded a white product which was recrystallized with analytical grade methanol. Yield was about 90%. m.p. 339 K. Spectral data IR (KBr) cm^-1: 2951 & 2891(CH₂ aliphatic), 1728(C=O ester),1602(aromatic C=C), 1469(CH aromatic). ¹H NMR(CDCl₃): 8.01(d, 2H, Ar—H), 7.43(m, 5H, Ar—H), 7.33(d, 1H, Ar—H),7.20(d, 2H, Ar—H), 7.10(d, 2H, Ar—H), 5.20(s, 2H, Ar—CH₂—O–), 2.56(t, 2H, Ar—CH₂–), 2.30(s, 3H, Ar—CH₃), 1.56(m,2H, Ar—CH₂—CH₂–), 1.30(m, 14H, aliphatic-CH₂–),0.9 (t, 3H, –CH₃). Elemental analysis: Molecular Weight, 458.63 for C₃₁ H₃₈O₃requires C 81.18%, H 8.35%. Found, C 80.71% H 8.50%.