[Journal logo]

Volume 68 
Part 12 
Page o3410  
December 2012  

Received 22 October 2012
Accepted 16 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.130
Data-to-parameter ratio = 18.9
Details
Open access

9-(4-Methoxyphenyl)anthracene

aCAS in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai-25, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai-25, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C21H16O, the dihedral angle between the anthracene ring system and the benzene ring is 74.3 (5)°. The anthracene ring system is essentially planar (r.m.s. deviation = 0.0257 Å) and the methoxy group lies in the plane of the benzene ring [C1-O1-C2-C7 torsion angle = 0.5 (2)°]. The crystal structure features [pi]-[pi] [centroid-centroid distance = 3.9487 (12) Å] and C-H...[pi] interactions, forming a sheet running along the a-axis direction.

Related literature

For applications of anthracene, see: Bae et al. (2010[Bae, S. Y., Jung, K. H., Hoang, M. H., Kim, K. H., Lee, T. W., Cho, M. J., Jin, J., Lee, D. H., Chung, D. S., Park, C. E. & Choi, D. H. (2010). Synth. Met. 160, 1022-1029.]); Debbab et al. (2012[Debbab, A., Aly, A. H., Edrada-Ebel, R., Wray, V., Pretsch, A., Pescitelli, G., Kurtan, T. & Proksch, P. (2012). Eur. J. Org. Chem. pp. 1351-1359.]). For a related structure, see: Wang et al. (2008[Wang, L., You, W., Huang, W., Jiang, J.-C. & Yao, C. (2008). Acta Cryst. E64, o487.]).

[Scheme 1]

Experimental

Crystal data
  • C21H16O

  • Mr = 284.34

  • Monoclinic, P 21 /c

  • a = 13.5539 (5) Å

  • b = 15.0626 (5) Å

  • c = 7.6130 (2) Å

  • [beta] = 99.219 (2)°

  • V = 1534.17 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 293 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.981, Tmax = 0.985

  • 14917 measured reflections

  • 3806 independent reflections

  • 2317 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.130

  • S = 1.02

  • 3806 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg4 are the centroids of the C2-C7 and C16-C21 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C7-H7...Cg4i 0.93 2.77 3.566 (2) 145
C11-H11...Cg1ii 0.93 2.87 3.724 (2) 154
C19-H19...Cg1iii 0.93 2.94 3.772 (2) 150
C21-H21...Cg4iv 0.93 2.88 3.711 (2) 150
Symmetry codes: (i) x, y, z-1; (ii) -x+1, -y, -z; (iii) -x+2, -y, -z+1; (iv) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2599 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. VS and DV also thank the UGC SAP for financial support.

References

Bae, S. Y., Jung, K. H., Hoang, M. H., Kim, K. H., Lee, T. W., Cho, M. J., Jin, J., Lee, D. H., Chung, D. S., Park, C. E. & Choi, D. H. (2010). Synth. Met. 160, 1022-1029.  [ISI] [CrossRef] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Debbab, A., Aly, A. H., Edrada-Ebel, R., Wray, V., Pretsch, A., Pescitelli, G., Kurtan, T. & Proksch, P. (2012). Eur. J. Org. Chem. pp. 1351-1359.  [CrossRef]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wang, L., You, W., Huang, W., Jiang, J.-C. & Yao, C. (2008). Acta Cryst. E64, o487.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3410  [ doi:10.1107/S1600536812047149 ]

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.