9-(4-Meth­oxy­phen­yl)anthracene

Silambarasan, V.; Srinivasan, T.; Sivasakthikumaran, R.; Mohanakrishnan, A.K.; Velmurugan, D.

doi:10.1107/S1600536812047149

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 (C-C) = 0.002 Å
R = 0.045
wR = 0.130
Data-to-parameter ratio = 18.9
Details

9-(4-Methoxyphenyl)anthracene

V. Silambarasan,^a T. Srinivasan,^a R. Sivasakthikumaran,^b A. K. Mohanakrishnan ^b and D. Velmurugan ^a ^*

^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); Debbab et al. (2012). For a related structure, see: Wang et al. (2008).

Experimental

Crystal data

C₂₁H₁₆O
M_r = 284.34
Monoclinic, P 2₁ /c
a = 13.5539 (5) Å
b = 15.0626 (5) Å
c = 7.6130 (2) Å
= 99.219 (2)°
V = 1534.17 (9) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.981, T_max = 0.985
14917 measured reflections
3806 independent reflections
2317 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.130
S = 1.02
3806 reflections
201 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C7-H7Cg4ⁱ	0.93	2.77	3.566 (2)	145
C11-H11Cg1ⁱⁱ	0.93	2.87	3.724 (2)	154
C19-H19Cg1ⁱⁱⁱ	0.93	2.94	3.772 (2)	150
C21-H21Cg4^iv	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); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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.
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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, L., You, W., Huang, W., Jiang, J.-C. & Yao, C. (2008). Acta Cryst. E64, o487.

organic compounds