5-Iodo-3-phenyl-2,1-benzoxazole

Yuriy Teslenko; Vasyl S Matiychuk; Vasyl Kinzhybalo; Tadeusz Lis; Mykola D Obushak

doi:10.1107/S1600536813005862

. 2013 Mar 9;69(Pt 4):o508. doi: 10.1107/S1600536813005862

5-Iodo-3-phenyl-2,1-benzoxazole

Yuriy Teslenko ^a,^*, Vasyl S Matiychuk ^a, Vasyl Kinzhybalo ^b, Tadeusz Lis ^c, Mykola D Obushak ^a

PMCID: PMC3629537 PMID: 23634055

Abstract

The title compound, C₁₃H₈INO, was prepared by a condensation reaction of 4-nitrobenzene with phenylacetonitrile in NaOH–ethanol solution. There are two independent molecules in the asymmetric unit, in which the dihedral angles between the benzene ring and the benzoisoxazole unit are 4.2 (3) and 4.1 (3)°. The crystal packing is governed by C—H⋯N, C—I⋯π and C—I⋯O interactions.

Related literature

For the biologial activity and applications of benzo[c]isoxazoles, see: McEvoy et al. (1968 ▶); Hester et al. (1989 ▶); Walsh et al. (1990 ▶); Angibaud et al. (2003 ▶). For a related structure, see: Teslenko et al. (2008 ▶). For a general synthetic procedure, see: Davis & Pizzini (1960 ▶).

Experimental

Crystal data

C₁₃H₈INO
M _r = 321.10
Monoclinic,
a = 5.381 (3) Å
b = 15.225 (7) Å
c = 13.749 (7) Å
β = 94.92 (3)°
V = 1122.2 (10) Å³
Z = 4
Mo Kα radiation
μ = 2.83 mm⁻¹
T = 100 K
0.25 × 0.08 × 0.03 mm

Data collection

Kuma KM-4-CCD four-circle diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006 ▶) T _min = 0.44, T _max = 0.80
15060 measured reflections
6015 independent reflections
4621 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.090
S = 1.00
6015 reflections
289 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 1.98 e Å⁻³
Δρ_min = −1.01 e Å⁻³
Absolute structure: Flack (1983 ▶), 1659 Friedel pairs
Flack parameter: 0.00 (3)

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(26.8KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005862/gk2554sup1.cif

e-69-0o508-sup1.cif^{(26.8KB, cif)}

Click here for additional data file.^{(294.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005862/gk2554Isup2.hkl

e-69-0o508-Isup2.hkl^{(294.4KB, hkl)}

Click here for additional data file.^{(2KB, cdx)}

Supplementary material file. DOI: 10.1107/S1600536813005862/gk2554Isup3.cdx

Click here for additional data file.^{(4.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813005862/gk2554Isup4.cml

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

Table 1. Intermolecular interactions (Å, °).

Cg is the centroid of the C1B–C6B ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3A—H3A⋯N1B ⁱ	0.95	2.40	3.247 (7)	149
C11A—H11A⋯N1A ⁱⁱ	0.95	2.47	3.339 (8)	152
C4A—I1A⋯Cg ⁱⁱⁱ	2.100 (5)	3.618 (2)	5.637 (6)	160.0 (2)
C4B—I1B⋯O1A	2.100 (5)	3.335 (5)	5.325 (7)	156.3 (2)

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

Acknowledgments

The authors are grateful to the State fund for fundamental research of Ukraine for the financial support (Project F54.3/004).

supplementary crystallographic information

Comment

Our interest in benzo[c]isoxazoles is concerned with their application as precursors of a variety of bioactive compounds (Angibaud et al., 2003; Walsh et al., 1990; Hester et al., 1989; McEvoy et al., 1968). The title compound will be used in our further investigations as arylation agent in palladium-catalyzed reactions with alkenes and alkynes.

The title compound crystalizes in the noncentrosymmetric monoclinic P2₁ space group with two independent molecules in the asymmetric part (A and B), see Fig. 1. The molecules are almost planar, the dihedral angles between the mean planes of benzoisoxazole and benzene rings being 4.2 (3)° and 4.1 (3)° for A and B, respectively. The geometrical parameters of the molecules are similar and consistent with the previously studied 2,1-benzoxazole derivatives (Teslenko et al., 2008).

Crystal packing is governed by hydrogen bonds of C–H···N type and other intermolecular interactions including C–I···π and C–I···O. Intermolecular interactions C4A–I1A···C_gⁱⁱⁱ (C_g is a centroid of C1B/C6B aromatic ring) and C4B–I1B···O1A connect the molecules into chains propagating in b-axis direction along 2₁ screw axis (see Fig. 2). Hydrogen bond C3A–H3A···N1Bⁱ connects the chains into corrugated layer parallel to the bc-plane. Hydrogen bond C11A–H11A···N1Aⁱⁱ binds successive layers.

Experimental

Phenylacetonitrile (1.4 g, 12 mmol) and 5 ml of benzene solution of 4-iodonitrobenene (2.49 g, 10 mmol) were added with stirring to 40 ml of ethanol solution of potassium hydroxide (4 g, 0.1 mole). The mixture was stirred for 4 h at 323 K, then poured into 150 ml of water and acidified with hydrochloric acid. The precipitate was isolated by filtration, washed with water and dried. Recrystallization of crude product from ethanol gave 2.57 g (80% yield) of 5-iodo-3-phenyl-2,1-benzoxazole as pale yellow needles suitable for X-ray analysis, m.p. 390–391 K.