[Journal logo]

Volume 69 
Part 12 
Pages o1804-o1805  
December 2013  

Received 15 October 2013
Accepted 15 November 2013
Online 23 November 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.025
wR = 0.074
Data-to-parameter ratio = 18.1
Details
Open access

Ethyl 3-(10-bromo­anthracen-9-yl)-5-methyl-1,2-oxazole-4-carboxyl­ate

aDepartment of Chemistry, Ithaca College, 953 Danby Road, Ithaca, NY 14850, USA, and bDepartment of Pharmaceutical & Biomedical Science, The University of Montana, 32 Campus Drive, Missoula, MT 59812, USA
Correspondence e-mail: nicholas.natale@umontana.edu

In the title compound, C21H16BrNO3, the mean planes of the anthracene tricycle and isoxazole ring are inclined to each other at a dihedral angle of 72.12 (7)°. The carb­oxy group is slightly out of the isoxazole mean plane, with a maximum deviation of 0.070 (5) Å for the carbonyl O atom. In the crystal, pairs of weak C-H...O hydrogen bonds link the mol­ecules into dimers, and weak C-H...N inter­actions further link these dimers into corrugated layers parallel to the bc plane.

Related literature

For the synthesis of anthryl isoxazoles, see: Mosher & Natale (1995[Mosher, M. D. & Natale, N. R. (1995). J. Heterocycl. Chem. 32, 779-781.]); Zhou et al. (1997[Zhou, P., Mosher, M. D., Taylor, W. D., Crawford, G. A. & Natale, N. R. (1997). Bioorg. Med. Chem. Lett. 7, 2455-2456.]); Han & Natale (2001[Han, X. & Natale, N. R. (2001). J. Heterocycl. Chem. 38, 415-418.]); Rider et al. (2010[Rider, K. C., Burkhart, D. J., Li, C., Mckenzie, A. R., Nelson, J. K. & Natale, N. R. (2010). Arkivoc, pp. 97-107.]); Mirzaei et al. (2012[Mirzaei, Y. R., Weaver, M. W., Steiger, S. A., Kearns, A. K., Gajewski, M. P., Rider, K. C., Beall, H. D. & Natale, N. R. (2012). Tetrahedron, 68, 10360-10364.]). For related structures, see: Mosher et al. (1996[Mosher, M. D., Natale, N. R. & Vij, A. (1996). Acta Cryst. C52, 2513-2515.]); Han et al. (2002[Han, X., Li, C., Rider, K. C., Blumenfeld, A., Twamley, B. & Natale, N. R. (2002). Tetrahedron Lett. 43, 7673-7677.], 2003[Han, X., Twamley, B. & Natale, N. R. (2003). J. Heterocycl. Chem. 40, 539-545.]); Li et al. (2006[Li, C., Twamley, B. & Natale, N. R. (2006). Acta Cryst. E62, o854-o856.], 2008[Li, C., Twamley, B. & Natale, N. R. (2008). J. Heterocycl. Chem. 45, 259-264.]). For the anti­tumor activity of aryl isoxazole amides (AIMs), see: Han et al. (2009[Han, X., Li, C., Mosher, M. D., Rider, K. C., Zhou, P., Crawford, R. L., Fusco, W., Paszczynski, A. & Natale, N. R. (2009). Bioorg. Med. Chem. 17, 1671-1680.]); Gajewski et al. (2009[Gajewski, M. P., Beall, H., Schnieder, M., Stranahan, S. M., Mosher, M. D., Rider, K. C. & Natale, N. R. (2009). Bioorg. Med. Chem. Lett. 19, 4067-4069.]); Balasubramanian et al. (2011[Balasubramanian, S., Hurley, L. H. & Neidle, S. (2011). Nat. Rev. Drug Discov. 10, 261-275.]); Neidle (2012[Neidle, S. (2012). In Therapeutic Applications of Quadruplex Nucleic Acids. Amsterdam: Elsevier/Academic Press.]); Kohn et al. (2012[Kohn, K. W., Zeeberg, B. R., Reinhold, W. C., Sunshine, M., Luna, A. & Pommier, Y. (2012). PLoS ONE, 7, e35716.]); Shoemaker (2006[Shoemaker, R. H. (2006). Nat. Rev. Cancer, 6, 816-823.]).

[Scheme 1]

Experimental

Crystal data
  • C21H16BrNO3

  • Mr = 410.26

  • Monoclinic, P 21 /c

  • a = 8.8437 (1) Å

  • b = 16.7099 (2) Å

  • c = 11.7157 (2) Å

  • [beta] = 92.419 (1)°

  • V = 1729.77 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.40 mm-1

  • T = 100 K

  • 0.49 × 0.47 × 0.38 mm

Data collection
  • Bruker SMART BREEZE CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Ins., Madison, Wisconsin, USA.]) Tmin = 0.39, Tmax = 0.47

  • 34958 measured reflections

  • 4290 independent reflections

  • 4128 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.025

  • wR(F2) = 0.074

  • S = 1.05

  • 4290 reflections

  • 237 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.51 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...N1i 0.95 2.54 3.4305 (19) 155
C4-H4...O2ii 0.95 2.58 3.1990 (18) 123
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Ins., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Ins., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2 and 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: CV5433 ).


Acknowledgements

The Bruker single-crystal X-ray diffraction facility was established at Ithaca College in 2012. NRN, MJC, MJW and ND thank the National Institutes of Health for grants NINDS P20RR015583 Center for Structural and Functional Neuroscience (CSFN) and P20 RR017670 Center for Environ­mental Health Sciences (CEHS), and the University of Montana Grant Program.

References

Balasubramanian, S., Hurley, L. H. & Neidle, S. (2011). Nat. Rev. Drug Discov. 10, 261-275.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Ins., Madison, Wisconsin, USA.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gajewski, M. P., Beall, H., Schnieder, M., Stranahan, S. M., Mosher, M. D., Rider, K. C. & Natale, N. R. (2009). Bioorg. Med. Chem. Lett. 19, 4067-4069.  [CrossRef] [PubMed] [ChemPort]
Han, X., Li, C., Mosher, M. D., Rider, K. C., Zhou, P., Crawford, R. L., Fusco, W., Paszczynski, A. & Natale, N. R. (2009). Bioorg. Med. Chem. 17, 1671-1680.  [CrossRef] [PubMed] [ChemPort]
Han, X., Li, C., Rider, K. C., Blumenfeld, A., Twamley, B. & Natale, N. R. (2002). Tetrahedron Lett. 43, 7673-7677.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Han, X. & Natale, N. R. (2001). J. Heterocycl. Chem. 38, 415-418.  [CrossRef] [ChemPort]
Han, X., Twamley, B. & Natale, N. R. (2003). J. Heterocycl. Chem. 40, 539-545.  [CrossRef] [ChemPort]
Kohn, K. W., Zeeberg, B. R., Reinhold, W. C., Sunshine, M., Luna, A. & Pommier, Y. (2012). PLoS ONE, 7, e35716.  [CrossRef] [PubMed]
Li, C., Twamley, B. & Natale, N. R. (2006). Acta Cryst. E62, o854-o856.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Li, C., Twamley, B. & Natale, N. R. (2008). J. Heterocycl. Chem. 45, 259-264.  [CrossRef] [ChemPort]
Mirzaei, Y. R., Weaver, M. W., Steiger, S. A., Kearns, A. K., Gajewski, M. P., Rider, K. C., Beall, H. D. & Natale, N. R. (2012). Tetrahedron, 68, 10360-10364.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Mosher, M. D. & Natale, N. R. (1995). J. Heterocycl. Chem. 32, 779-781.  [CrossRef] [ChemPort]
Mosher, M. D., Natale, N. R. & Vij, A. (1996). Acta Cryst. C52, 2513-2515.  [CSD] [CrossRef] [IUCr Journals]
Neidle, S. (2012). In Therapeutic Applications of Quadruplex Nucleic Acids. Amsterdam: Elsevier/Academic Press.
Rider, K. C., Burkhart, D. J., Li, C., Mckenzie, A. R., Nelson, J. K. & Natale, N. R. (2010). Arkivoc, pp. 97-107.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shoemaker, R. H. (2006). Nat. Rev. Cancer, 6, 816-823.  [Web of Science] [CrossRef]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zhou, P., Mosher, M. D., Taylor, W. D., Crawford, G. A. & Natale, N. R. (1997). Bioorg. Med. Chem. Lett. 7, 2455-2456.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1804-o1805   [ doi:10.1107/S1600536813031395 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.