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Volume 68 
Part 11 
Pages o3086-o3087  
November 2012  

Received 12 September 2012
Accepted 1 October 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.003 Å
R = 0.022
wR = 0.055
Data-to-parameter ratio = 13.4
Details
Open access

Bicyclo[2.2.1]hept-7-yl p-bromobenzoate

aDepartment of Chemistry, Weber State University, Ogden, Utah 84408-2503, and bDepartment of Chemistry, University of Utah, Salt Lake City, Utah, 84112, USA
Correspondence e-mail: blloyd@weber.edu

The title compound, C14H15BrO2, contains a sterically unencumbered norbornyl group. The dihedral angle between the plane of the carboxylate group and the mean plane of the adjacent benzene ring is 5.3 (2)°. The dihedral angle between the plane of the carboxylate group and the norbornyl methano C-O bond is 4.5 (1)°, the methano C atom deviating by 0.141 (2) Å from this plane. In the crystal, molecules pack as pairs of enantiomers, with a distance of 3.747 (1) Å between the centroids of nearest parallel benzene rings.

Related literature

For calculated and experimental norbornane and related structures, see: Allinger et al. (1989[Allinger, N. L., Geise, H. J., Pyckhout, W., Paquette, L. A. & Gallucci, J. C. (1989). J. Am. Chem. Soc. 111, 1106-1114.]); Pfund et al. (1980[Pfund, R. A., Schweizer, W. B. & Ganter, C. (1980). Helv. Chim. Acta, 63, 674-681.]). For related polycyclic p-bromobenzoate structures, see: Lloyd & Arif (2012[Lloyd, B. A. & Arif, A. M. (2012). Acta Cryst. E68, o2209.]); Lloyd et al. (1995[Lloyd, B. A., Arif, A. M., Coots, R. J. & Allred, E. L. (1995). Acta Cryst. C51, 2059-2062.], 2000[Lloyd, B. A., Arif, A. M. & Allred, E. L. (2000). Acta Cryst. C56, 1377-1379.]). For a high resolution low temperature powder synchrotron X-ray diffraction structure of norbornane, see: Fitch & Jobic (1993[Fitch, A. N. & Jobic, H. (1993). J. Chem. Soc. Chem. Commun. pp. 1516-1517.]). For some norbornyl bond lengths and angles, see: Watson et al. (1992[Watson, W. H., Kashyap, R. P., Krawiec, M., Marchand, A. P., Reddy, C. M. & Gadgil, V. R. (1992). Acta Cryst. B48, 731-737.]). For possible C-O bond-length correlation to reactivity in a 7-norbornenyl benzoate, see: Jones et al. (1992[Jones, P. G., Kirby, A. J. & Percy, J. M. (1992). Acta Cryst. C48, 829-832.]).

[Scheme 1]

Experimental

Crystal data
  • C14H15BrO2

  • Mr = 295.17

  • Monoclinic, P 21 /c

  • a = 11.7401 (2) Å

  • b = 6.3767 (1) Å

  • c = 17.7462 (3) Å

  • [beta] = 109.584 (1)°

  • V = 1251.68 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.27 mm-1

  • T = 150 K

  • 0.30 × 0.25 × 0.18 mm

Data collection
  • Nonius KappaCCD Diffractometer

  • Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.440, Tmax = 0.591

  • 5495 measured reflections

  • 2882 independent reflections

  • 2469 reflections with I > 2[sigma](I)

  • Rint = 0.015

Refinement
  • R[F2 > 2[sigma](F2)] = 0.022

  • wR(F2) = 0.055

  • S = 1.03

  • 2882 reflections

  • 215 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN; 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]) 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: FJ2598 ).


Acknowledgements

We thank the Weber State Chemistry Department for supporting this work, the University of Utah Chemistry Department X-ray crystallographic facility, and the late Professor Evan L. Allred who began this work.

References

Allinger, N. L., Geise, H. J., Pyckhout, W., Paquette, L. A. & Gallucci, J. C. (1989). J. Am. Chem. Soc. 111, 1106-1114.  [CrossRef] [ChemPort] [ISI]
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.  [ISI] [CrossRef] [ChemPort] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fitch, A. N. & Jobic, H. (1993). J. Chem. Soc. Chem. Commun. pp. 1516-1517.  [CrossRef] [ISI]
Jones, P. G., Kirby, A. J. & Percy, J. M. (1992). Acta Cryst. C48, 829-832.  [CrossRef] [details]
Lloyd, B. A. & Arif, A. M. (2012). Acta Cryst. E68, o2209.  [CSD] [CrossRef] [details]
Lloyd, B. A., Arif, A. M. & Allred, E. L. (2000). Acta Cryst. C56, 1377-1379.  [CrossRef] [details]
Lloyd, B. A., Arif, A. M., Coots, R. J. & Allred, E. L. (1995). Acta Cryst. C51, 2059-2062.  [CSD] [CrossRef] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Pfund, R. A., Schweizer, W. B. & Ganter, C. (1980). Helv. Chim. Acta, 63, 674-681.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Watson, W. H., Kashyap, R. P., Krawiec, M., Marchand, A. P., Reddy, C. M. & Gadgil, V. R. (1992). Acta Cryst. B48, 731-737.  [CrossRef] [ISI] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3086-o3087   [ doi:10.1107/S1600536812041268 ]

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