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Volume 69 
Part 5 
Pages o667-o668  
May 2013  

Received 25 March 2013
Accepted 2 April 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.055
wR = 0.168
Data-to-parameter ratio = 12.3
Details
Open access

2-(4-Methylphenyl)-6-nitro-1,3-benzoxazole

aDipartimento di Scienze Chimiche, Università degli Studi di Napoli 'Federico II', Complesso di Monte S. Angelo, Via Cinthia, 80126 Napoli, Italy
Correspondence e-mail: roberto.centore@unina.it

The title compound, C14H10N2O3, is a [pi]-conjugated molecule containing a benzoxazole aromatic fused heterobicycle. The benzoxazole ring system is planar within 0.01 Å. The molecule assumes an approximately flat conformation, the benzoxazole ring system forming dihedral angles of 6.52 (12) and 7.4 (3)° with the benzene ring and the nitro group, respectively. In the crystal, molecules are connected by very weak C-H...O hydrogen interactions, forming chains running parallel to the a or c axes. The methyl H atoms are disordered over two sets of sites of equal occupancy rotated by 60°.

Related literature

For general information on heterocycles in organic electronics and optoelectronics, see: Dalton (2002[Dalton, L. (2002). Adv. Polym. Sci. 158, 1-86.]); Heeger (2010[Heeger, A. J. (2010). Chem. Soc. Rev. 39, 2354-2371.]). For heterocycle-based semiconductors, optoelectronic and piezoelectric materials, see: Carella, Centore, Sirigu et al. (2004[Carella, A., Centore, R., Sirigu, A., Tuzi, A., Quatela, A., Schutzmann, S. & Casalboni, M. (2004). Macromol. Chem. Phys. 205, 1948-1954.]); Centore, Ricciotti et al. (2012[Centore, R., Ricciotti, L., Carella, A., Roviello, A., Causà, M., Barra, M., Ciccullo, F. & Cassinese, A. (2012). Org. Electron. 13, 2083-2093.]); Centore, Concilio et al. (2012[Centore, R., Concilio, A., Borbone, F., Fusco, S., Carella, A., Roviello, A., Stracci, G. & Gianvito, A. (2012). J. Polym. Sci. Part B Polym. Phys. 50, 650-655.]). For structural and theoretical analysis of conjugation in heterocycle-based organic molecules, see: Carella, Centore, Fort et al. (2004[Carella, A., Centore, R., Fort, A., Peluso, A., Sirigu, A. & Tuzi, A. (2004). Eur. J. Org. Chem. pp. 2620-2626.]); Gainsford et al. (2008[Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2008). Acta Cryst. C64, o616-o619.]). For structural and theoretical analysis of conjugation in heterocycle-based metallorganic compounds, see: Takjoo et al. (2011[Takjoo, R., Centore, R., Hakimi, M., Beyramabadi, A. S. & Morsali, A. (2011). Inorg. Chim. Acta, 371, 36-41.]); Takjoo & Centore (2013[Takjoo, R. & Centore, R. (2013). J. Mol. Struct. 1031, 180-185.]). For theoretical computations on similar compounds, see: Capobianco et al. (2012[Capobianco, A., Esposito, A., Caruso, T., Borbone, F., Carella, A., Centore, R. & Peluso, A. (2012). Eur. J. Org. Chem. pp. 2980-2989.], 2013[Capobianco, A., Centore, R., Noce, C. & Peluso, A. (2013). Chem. Phys. 411, 11-16.]). For the synthesis of related heterocyclic compounds, see: Bruno et al. (2002[Bruno, V., Castaldo, A., Centore, R., Sirigu, A., Sarcinelli, F., Casalboni, M. & Pizzoferrato, R. (2002). J. Polym. Sci. Part A Polym. Chem. 40, 1468-1475.]); Centore et al. (2007[Centore, R., Riccio, P., Fusco, S., Carella, A., Quatela, A., Schutzmann, S., Stella, F. & De Matteis, F. (2007). J. Polym. Sci. Part A Polym. Chem. 45, 2719-2725.]); Piccialli et al. (2013[Piccialli, V., D'Errico, S., Borbone, N., Oliviero, G., Centore, R. & Zaccaria, S. (2013). Eur. J. Org. Chem. In the press. doi:10.1002/ejoc.201201554.]); Centore, Fusco, Capobianco et al. (2013[Centore, R., Fusco, S., Capobianco, A., Piccialli, V., Zaccaria, S. & Peluso, A. (2013). Eur. J. Org. Chem. In the press. doi:10.1002/ejoc.201201653.]). For hydrogen bonding in crystals see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). In The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press Inc.]); Centore, Fusco, Jazbinsek et al. (2013[Centore, R., Fusco, S., Jazbinsek, M., Capobianco, A. & Peluso, A. (2013). CrystEngComm. 15, 3318-3325.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10N2O3

  • Mr = 254.24

  • Orthorhombic, P b c a

  • a = 27.251 (4) Å

  • b = 7.4457 (6) Å

  • c = 11.990 (9) Å

  • V = 2432.8 (19) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.40 × 0.20 × 0.20 mm

Data collection
  • Enraf-Nonius MACH3 diffractometer

  • 2968 measured reflections

  • 2140 independent reflections

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

  • Rint = 0.020

  • 1 standard reflections every 120 min intensity decay: none

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.168

  • S = 1.11

  • 2140 reflections

  • 174 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10...O2i 0.93 2.61 3.502 (6) 160
C1-H1B...O2ii 0.96 2.80 3.143 (5) 102
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z].

Data collection: MACH3/PC Software (Nonius, 1996[Nonius (1996). MACH3/PC and CAD-4-PC. Nonius BV, Delft, The Netherlands.]); cell refinement: CELLFITW (Centore, 2004[Centore, R. (2004). CELLFITW. Università degli Studi di Napoli "Federico II", Naples, Italy.]); data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5053 ).


Acknowledgements

The authors thank the Centro Interdipartimentale di Metodologie Chimico-Fisiche, Università degli Studi di Napoli "Federico II", for support.

References

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Bruno, V., Castaldo, A., Centore, R., Sirigu, A., Sarcinelli, F., Casalboni, M. & Pizzoferrato, R. (2002). J. Polym. Sci. Part A Polym. Chem. 40, 1468-1475.  [CrossRef] [ChemPort]
Capobianco, A., Centore, R., Noce, C. & Peluso, A. (2013). Chem. Phys. 411, 11-16.  [ISI] [CrossRef] [ChemPort]
Capobianco, A., Esposito, A., Caruso, T., Borbone, F., Carella, A., Centore, R. & Peluso, A. (2012). Eur. J. Org. Chem. pp. 2980-2989.  [CSD] [CrossRef]
Carella, A., Centore, R., Fort, A., Peluso, A., Sirigu, A. & Tuzi, A. (2004). Eur. J. Org. Chem. pp. 2620-2626.  [CSD] [CrossRef]
Carella, A., Centore, R., Sirigu, A., Tuzi, A., Quatela, A., Schutzmann, S. & Casalboni, M. (2004). Macromol. Chem. Phys. 205, 1948-1954.  [ISI] [CSD] [CrossRef] [ChemPort]
Centore, R. (2004). CELLFITW. Università degli Studi di Napoli "Federico II", Naples, Italy.
Centore, R., Concilio, A., Borbone, F., Fusco, S., Carella, A., Roviello, A., Stracci, G. & Gianvito, A. (2012). J. Polym. Sci. Part B Polym. Phys. 50, 650-655.  [ISI] [CrossRef] [ChemPort]
Centore, R., Fusco, S., Capobianco, A., Piccialli, V., Zaccaria, S. & Peluso, A. (2013). Eur. J. Org. Chem. In the press. doi:10.1002/ejoc.201201653.
Centore, R., Fusco, S., Jazbinsek, M., Capobianco, A. & Peluso, A. (2013). CrystEngComm. 15, 3318-3325.  [CSD] [CrossRef] [ChemPort]
Centore, R., Riccio, P., Fusco, S., Carella, A., Quatela, A., Schutzmann, S., Stella, F. & De Matteis, F. (2007). J. Polym. Sci. Part A Polym. Chem. 45, 2719-2725.  [CrossRef] [ChemPort]
Centore, R., Ricciotti, L., Carella, A., Roviello, A., Causà, M., Barra, M., Ciccullo, F. & Cassinese, A. (2012). Org. Electron. 13, 2083-2093.  [ISI] [CrossRef] [ChemPort]
Dalton, L. (2002). Adv. Polym. Sci. 158, 1-86.  [CrossRef] [ChemPort]
Desiraju, G. R. & Steiner, T. (1999). In The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press Inc.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2008). Acta Cryst. C64, o616-o619.  [CSD] [CrossRef] [ChemPort] [details]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Heeger, A. J. (2010). Chem. Soc. Rev. 39, 2354-2371.  [ISI] [CrossRef] [ChemPort] [PubMed]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Nonius (1996). MACH3/PC and CAD-4-PC. Nonius BV, Delft, The Netherlands.
Piccialli, V., D'Errico, S., Borbone, N., Oliviero, G., Centore, R. & Zaccaria, S. (2013). Eur. J. Org. Chem. In the press. doi:10.1002/ejoc.201201554.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Takjoo, R. & Centore, R. (2013). J. Mol. Struct. 1031, 180-185.  [ISI] [CSD] [CrossRef] [ChemPort]
Takjoo, R., Centore, R., Hakimi, M., Beyramabadi, A. S. & Morsali, A. (2011). Inorg. Chim. Acta, 371, 36-41.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o667-o668   [ doi:10.1107/S1600536813008970 ]

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