Crystal structure of 5-(1-benzo­furan-2-yl)-3-(4-methyl­phen­yl)-4,5-di­hydro-1,2-oxazol-5-ol

A J Ravi; A C Vinayaka; S Jeyaseelan; M P Sadashiva; H C Devarajegowda

doi:10.1107/S2056989015011263

. 2015 Jun 17;71(Pt 7):o492–o493. doi: 10.1107/S2056989015011263

Crystal structure of 5-(1-benzofuran-2-yl)-3-(4-methylphenyl)-4,5-dihydro-1,2-oxazol-5-ol

A J Ravi ^a, A C Vinayaka ^b, S Jeyaseelan ^c, M P Sadashiva ^b, H C Devarajegowda ^a,^*

PMCID: PMC4518973 PMID: 26279925

Abstract

In the title compound, C₁₈H₁₅NO₃, the isoxazole moiety adopts a shallow envelope conformation, with the C atom bearing the OH group displaced by 0.148 (1) Å from the mean plane through the other four atoms. The mean plane of this ring (all atoms) subtends dihedral angles of 87.19 (6) and 15.51 (7)° with the benzofuran ring system (r.m.s. deviation = 0.007 Å) and the 4-methylphenyl ring, respectively. In the crystal, molecules are linked by O—H⋯N hydrogen bonds, generating [001] C(5) chains, with adjacent molecules in the chain related by c-glide symmetry. Weak C—H⋯O interactions link the chains into a three-dimensional network.

Keywords: crystal structure; benzofuran; 1,2-oxazole; alcohol; biological properties; pharmaceutical properties

Related literature

For the biological and pharmaceutical properties of isoxazoles, see: Eddington et al. (2002 ▸); Lee et al. (2009 ▸); Rozman et al. (2002 ▸); Shin et al. (2005 ▸). graphic file with name e-71-0o492-scheme1.jpg

Experimental

Crystal data

C₁₈H₁₅NO₃
M _r = 293.31
Monoclinic,
a = 10.2200 (15) Å
b = 14.2289 (19) Å
c = 10.2474 (15) Å
β = 93.058 (7)°
V = 1488.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
23993 measured reflections
3452 independent reflections
2829 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.123
S = 1.03
3452 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015011263/hb7438sup1.cif

e-71-0o492-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015011263/hb7438Isup2.hkl

e-71-0o492-Isup2.hkl^{(169.3KB, hkl)}

Click here for additional data file.^{(5.9KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015011263/hb7438Isup3.cml

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S2056989015011263/hb7438fig1.tif

Perspective diagram of the molecule with 50% probability displacement ellipsoids.

Click here for additional data file.^{(1.3MB, tif)}

a . DOI: 10.1107/S2056989015011263/hb7438fig2.tif

Packing diagram of the molecule viewed down the a axis.

CCDC reference: 1405867

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
O13H13N9ⁱ	0.82	2.17	2.9352(15)	156
C2H2O10ⁱⁱ	0.93	2.46	3.2328(17)	141
C7H7CO15ⁱⁱⁱ	0.96	2.58	3.175(2)	121
C18H18O10ⁱ	0.93	2.54	3.4183(17)	158

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

supplementary crystallographic information

S1. Comment

Isoxazole derivatives bearing various substituents are known to have diverse biological and pharmaceutical activities; such as antiviral (Lee et al., 2009), anti-HIV activities (Shin et al., 2005) and anticonvulsant activity (Eddington et al., 2002). In addition, isoxazole derivative is used for the treatment of rheumatoid arthritis (Rozman et al., 2002). As part of our interest in these compounds, the title compound was chosen for the X-ray structure analysis.

In the molecular structure of the title compound (Fig. 1), the isoxazole moiety makes dihedral angles of 87.19 (6)° and 15.51 (7)° with benzofuran and phenyl ring, respectively. The dihedral angle between the benzofuran and phenyl ring is 81.67 (6)° The central isoxazole moiety adopts a slightly flattened envelope conformation with puckering parameter Q = 0.2406 (12) Å and φ = 183.41 (17)° , and the maximum deviation found on the puckered atom at C11 is -0.148 (1) Å. The crystal structure features C—H···O and O—H···N hydrogen bonds. The packing diagram of the molecule when viewed down the a axis as shown in Fig. 2.

S2. Experimental

A solution of 2 Eq. of K₂CO₃ in water (1 ml) was added to the stirred solution of 4 Eq. of N-hydroxyl-4-toluenesulfonamide in MeOH/H₂O (5/1 ml). Then 1 Eq. of 1-Benzofuran-2-yl-3-p-tolyl-propenone was added and reaction mixture was allowed to stir at room temperature for overnight. After completion of reaction, the reaction mixture was diluted with EtOAc, washed with water and brine. The organic extract was dried and concentrated under reduced pressure to give crude product, which was further purified using column chromatography (60–120 silica gel) to afford pure product.