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Volume 69 
Part 4 
Page o508  
April 2013  

Received 2 February 2013
Accepted 28 February 2013
Online 9 March 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.008 Å
R = 0.041
wR = 0.090
Data-to-parameter ratio = 20.8
Details
Open access

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

aDepartment of Organic Chemistry, Ivan Franko National University of Lviv, Kyryla and Mefodiya 6, Lviv 79005, Ukraine,bInstitute of Low Temperature and Structure Research, Okolna 2, 50-422 Wroclaw, Poland, and cFaculty of Chemistry, University of Wroclaw, 14 Joliot-Curie St, 50-383 Wroclaw, Poland
Correspondence e-mail: dangercorp@gmail.com

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...[pi] and C-I...O interactions.

Related literature

For the biologial activity and applications of benzo[c]isoxazoles, see: McEvoy et al. (1968[McEvoy, F. J., Greenblatt, E. N., Osterrerg, A. C. & Allen, G. R. Jr (1968). J. Med. Chem. 11, 1248-1250.]); Hester et al. (1989[Hester, J. B., Ludens, J. H., Emmert, D. E. & West, B. E. (1989). J. Med. Chem. 32, 1157-1163.]); Walsh et al. (1990[Walsh, D. A., Moran, H. W., Shamblee, D. A. & Welstead, W. J. (1990). J. Med. Chem. 33, 2296-2304.]); Angibaud et al. (2003[Angibaud, P., Bourdrez, X., Devine, A., End, D. W., Freyne, E., Ligny, Y., Muller, P., Mannens, G., Pilatte, I., Poncelet, V., Skrzat, S., Smets, G., Van Dun, J., Van Remoortere, P., Venet, M. & Wouters, W. (2003). Bioorg. Med. Chem. Lett. 13, 1543-1548.]). For a related structure, see: Teslenko et al. (2008[Teslenko, Y., Matiychuk, V., Obushak, M., Kinzhybalo, V. & Slepokura, K. (2008). Acta Cryst. E64, o2420.]). For a general synthetic procedure, see: Davis & Pizzini (1960[Davis, R. B. & Pizzini, L. C. (1960). J. Org. Chem. 25, 1884-1888.]).

[Scheme 1]

Experimental

Crystal data
  • C13H8INO

  • Mr = 321.10

  • Monoclinic, P 21

  • a = 5.381 (3) Å

  • b = 15.225 (7) Å

  • c = 13.749 (7) Å

  • [beta] = 94.92 (3)°

  • V = 1122.2 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]) Tmin = 0.44, Tmax = 0.80

  • 15060 measured reflections

  • 6015 independent reflections

  • 4621 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.090

  • S = 1.00

  • 6015 reflections

  • 289 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 1.98 e Å-3

  • [Delta][rho]min = -1.01 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1659 Friedel pairs

  • Flack parameter: 0.00 (3)

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...N1Bi 0.95 2.40 3.247 (7) 149
C11A-H11A...N1Aii 0.95 2.47 3.339 (8) 152
C4A-I1A...Cgiii 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)
Symmetry codes: (i) x, y, z-1; (ii) [-x-1, y-{\script{1\over 2}}, -z+1]; (iii) [-x+1, y-{\script{1\over 2}}, -z+1].

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2554 ).


Acknowledgements

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

References

Angibaud, P., Bourdrez, X., Devine, A., End, D. W., Freyne, E., Ligny, Y., Muller, P., Mannens, G., Pilatte, I., Poncelet, V., Skrzat, S., Smets, G., Van Dun, J., Van Remoortere, P., Venet, M. & Wouters, W. (2003). Bioorg. Med. Chem. Lett. 13, 1543-1548.  [CrossRef] [PubMed] [ChemPort]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Davis, R. B. & Pizzini, L. C. (1960). J. Org. Chem. 25, 1884-1888.  [CrossRef] [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Hester, J. B., Ludens, J. H., Emmert, D. E. & West, B. E. (1989). J. Med. Chem. 32, 1157-1163.  [CrossRef] [ChemPort] [PubMed] [ISI]
McEvoy, F. J., Greenblatt, E. N., Osterrerg, A. C. & Allen, G. R. Jr (1968). J. Med. Chem. 11, 1248-1250.  [CrossRef] [ChemPort] [PubMed] [ISI]
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Teslenko, Y., Matiychuk, V., Obushak, M., Kinzhybalo, V. & Slepokura, K. (2008). Acta Cryst. E64, o2420.  [CSD] [CrossRef] [details]
Walsh, D. A., Moran, H. W., Shamblee, D. A. & Welstead, W. J. (1990). J. Med. Chem. 33, 2296-2304.  [CrossRef] [ChemPort] [PubMed] [ISI]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o508  [ doi:10.1107/S1600536813005862 ]

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