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Volume 69 
Part 7 
Pages o1138-o1139  
July 2013  

Received 13 May 2013
Accepted 18 June 2013
Online 22 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.026
wR = 0.066
Data-to-parameter ratio = 15.5
Details
Open access

(E)-Methyl 3-(10-bromoanthracen-9-yl)acrylate

aInstitute of Inorganic Chemistry, University of Hamburg, Hamburg, Germany,bDepartment of Chemical Engineering, United Arab Emirates University, AL Ain, Abu Dhabi, United Arab Emirates, and cDepartment of Chemistry, United Arab Emirates University, AL Ain, Abu Dhabi, United Arab Emirates
Correspondence e-mail: thies@uaeu.ac.ae

In the title molecule, C18H13BrO2, the anthracene unit forms an angle of 46.91 (2)° with the mean plane of the methyl acrylate moiety. In the crystal, the molecules arrange themselves into strands parallel to [010] and, due to the crystal symmetry, there are eight strands crossing the unit cell. In each strand, molecules form short C-H...O and C-H...[pi] contacts and have their anthracene groups parallel to each other. Neighboring strands, related by a c-glide operation, are connected via C-H...O interactions and form a layer parallel to (100). The arrangement of the acrylate and anthracene groups in the crystal do not allow for [2 + 2] or [4 + 4] cycloaddition.

Related literature

For an analogous preparation of the title compound, see: Bugenhagen et al. (2013[Bugenhagen, B., Al Jasem, Y., Hindawi, B. al, Al Rawashdeh, N. & Thiemann, T. (2013). Acta Cryst. E69, o130-o131.]); Nguyen & Weizman (2007[Nguyen, K. & Weizman, H. (2007). J. Chem. Educ. 84, 119-121.]). For crystal structures of photodimerizable aryl-enes, see: Vishnumurthy et al. (2002[Vishnumurthy, K., Guru Row, T. N. & Venkatesan, K. (2002). Photochem. Photobiol. Sci. 1, 427-430.]); Mascitti & Corey (2006[Mascitti, V. & Corey, E. J. (2006). Tetrahedron Lett. 47, 5879-5882.]); Sonoda (2011[Sonoda, Y. (2011). Molecules, 16, 119-148.]); Schmidt (1964[Schmidt, G. M. J. (1964). J. Chem. Soc. pp. 2014-2021.]). For the photodimerization of anthracenes in the crystal, see: Schmidt (1971[Schmidt, G. M. J. (1971). J. Pure Appl. Chem. 27, 647-678.]); Ihmels et al. (2000[Ihmels, H., Leusser, D., Pfeiffer, M. & Stalke, D. (2000). Tetrahedron, 56, 6867-6875.]). For the X-ray crystal structure of a non-planar bromoanthracene, see: Barkhuizen et al. (2004[Barkhuizen, D. A., Howie, R. A., Maguire, G. E. M. & Rademeyer, M. (2004). Acta Cryst. E60, o571-o573.]).

[Scheme 1]

Experimental

Crystal data
  • C18H13BrO2

  • Mr = 341.19

  • Orthorhombic, P b c n

  • a = 40.5848 (4) Å

  • b = 5.32093 (5) Å

  • c = 13.0710 (1) Å

  • V = 2822.67 (5) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 3.98 mm-1

  • T = 100 K

  • 0.21 × 0.19 × 0.13 mm

Data collection
  • Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer

  • Absorption correction: analytical (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.891, Tmax = 0.924

  • 25313 measured reflections

  • 2961 independent reflections

  • 2900 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.026

  • wR(F2) = 0.066

  • S = 1.12

  • 2961 reflections

  • 191 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2-C7 ring.

D-H...A D-H H...A D...A D-H...A
C15-H15...Cg1i 0.93 2.91 (2) 3.5055 (19) 123
C16-H16...O2ii 0.93 2.40 3.315 (3) 170
C5-H5...O2iii 0.93 2.53 3.372 (2) 150
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z; (iii) [x, -y+1, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.]) within 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.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and 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.]); software used to prepare material for publication: SHELXL97 and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2574 ).


Acknowledgements

The authors thank UAEU interdisciplinary grant 31S036 for financial support.

References

Agilent (2013). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Barkhuizen, D. A., Howie, R. A., Maguire, G. E. M. & Rademeyer, M. (2004). Acta Cryst. E60, o571-o573.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Bugenhagen, B., Al Jasem, Y., Hindawi, B. al, Al Rawashdeh, N. & Thiemann, T. (2013). Acta Cryst. E69, o130-o131.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
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]
Ihmels, H., Leusser, D., Pfeiffer, M. & Stalke, D. (2000). Tetrahedron, 56, 6867-6875.  [Web of Science] [CSD] [CrossRef] [ChemPort]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Mascitti, V. & Corey, E. J. (2006). Tetrahedron Lett. 47, 5879-5882.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Nguyen, K. & Weizman, H. (2007). J. Chem. Educ. 84, 119-121.  [CrossRef] [ChemPort]
Schmidt, G. M. J. (1964). J. Chem. Soc. pp. 2014-2021.  [CrossRef]
Schmidt, G. M. J. (1971). J. Pure Appl. Chem. 27, 647-678.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sonoda, Y. (2011). Molecules, 16, 119-148.  [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Vishnumurthy, K., Guru Row, T. N. & Venkatesan, K. (2002). Photochem. Photobiol. Sci. 1, 427-430.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1138-o1139   [ doi:10.1107/S1600536813016905 ]

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