3-[Chloro­(phen­yl)meth­yl]-6-methyl-1,2-benzoxazole

M Kayalvizhi; G Vasuki; K Ramamurthi; A Veerareddy; G Laxminarasimha

doi:10.1107/S1600536811042462

. 2011 Oct 22;67(Pt 11):o2999. doi: 10.1107/S1600536811042462

3-[Chloro(phenyl)methyl]-6-methyl-1,2-benzoxazole

M Kayalvizhi ^a, G Vasuki ^a,^*, K Ramamurthi ^b, A Veerareddy ^c, G Laxminarasimha ^c

PMCID: PMC3247399 PMID: 22220017

Abstract

The title compound, C₁₅H₁₂ClNO, is a functionalized 1,2-benzoxazole with a chloro(phenyl)methyl substituent. The molecule is V-shaped, the dihedral angle between the mean plane of the 1,2-benzoxazole system [maximum deviation = 0.023 (3) Å for the N atom] and the phenyl ring being 70.33 (14)°. There are no hydrogen-bonding interactions in the crystal structure, which is stabilized by van der Waals interactions only.

Related literature

For the synthesis of the title compound, see: Veerareddy et al. (2011 ▶). For related structures, see: Atovmyan & Aliev (1994 ▶); Hu et al. (2009 ▶); Korlyukov et al. (2003 ▶).

Experimental

Crystal data

C₁₅H₁₂ClNO
M _r = 257.71
Monoclinic,
a = 13.2075 (8) Å
b = 6.5888 (4) Å
c = 15.1224 (8) Å
β = 103.738 (3)°
V = 1278.33 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.919, T _max = 0.945
10507 measured reflections
2087 independent reflections
1621 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.125
S = 1.06
2087 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008) ▶; software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042462/su2326sup1.cif

e-67-o2999-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042462/su2326Isup2.hkl

e-67-o2999-Isup2.hkl^{(100.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811042462/su2326Isup3.cml

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

Acknowledgments

VG thanks the UGC, India, for financial assistance under the Minor Research Project (2010–2011) and also thanks the Sophisticated Analytical Instrument Facility, IIT Madras, Chennai, for the X-ray data collection.

supplementary crystallographic information

Comment

Benzisoxazole is an aromatic organic compound with a molecular formula C₇H₅NO containing a benzene-fused isoxazole ring structure. Benzisoxazole is primarily used in industry and research. Being a heterocyclic compound, benzisoxazole finds use in research as a starting material for the synthesis of larger, usually bioactive structures. Isoxazole and benzisoxazole are important classes of nitrogen-oxygen containing heterocycles. They have extensive applications as structural units of various biologically important molecules and as useful intermediates in medicinal chemistry. Among them, 3–substituted–1,2–benzisoxazole and their derivatives are emerging as potential antipsychotic compounds. For example, 1,2–benzisoxazole–3–methanesulfonamide, also known as zonisamide, is an efficient antiseizure agent. It has been reported that it blocks the repetitive firing of voltage–sensitive sodium channels and reduces voltage–sensitive T–type calcium currents (Veerareddy et al., 2011).

In molecular structure of the title functionalized 1,2-benzoxazole compound, (I), is illustrated in Fig. 1. The bond length and angles are in agreement with those found for closely related structures, for example, 6-tert-butyl-4,5-dichloro-3-ethyl-4,5-dihydro-2,1-benzoisoxazole (II) [Atovmyan & Aliev, 1994], 3-(1,3-dioxolan-2-yl)-4,6-dinitrobenzo[d]isoxazole (III) [Korlyukov et al., 2003], and N-Phenyl-4-(8-phenyl-4,5-dihydro-1,2-benzoxazolo- [4,5-d]thiazol-2-yl)-piperidine-1-carboxamide (IV) [Hu et al., 2009]. The widening of the exocyclic angle C10—C9—C3 [113.4 (2)°] from the normal value of 109° may be due to repulsion between neighbouring H atoms [H9··· H11 = 2.2495 (1) Å]. The exocyclic angles C9—C3—C3a [132.1 (2)°] and C3—C3a—C4 [138.2 (2)°] deviate significantly from the normal value of 120° and this may be due to the intramolecular non-bonded interactions between the chlorine atom and H-atom H4 at C10 [Cl··· H4 = 3.1169 (7) Å]. The isoxazole ring (O1,N2,C3,C3a,C7a) is planar [max. deviation 0.007 (3) Å], with the chloro(phenyl)methyl substituent being nearly normal to the plane of the five membered ring [N2-C3-C9-C10 = 100.1 (3)°], similar to the situation in compound (II) (Atovmyan & Aliev, 1994). The dihedral angle between the mean plane of the 1,2-benzoxazole [max. deviation 0.023 (3) Å] and the phenyl ring (C10-C15) is 70.33 (14)°.

Crystal packing of compound (I) is illustrated in Fig. 2. There are no significant non-bonded interactions present and the crystal structure is stabilized by van der Waals interactions only.

Experimental

The compound was synthesized following the published procedure (Veerareddy et al., 2011).