(2E)-3-(2-Anthracen-2-yl)-1-(2-hy­droxy­phen­yl)prop-2-en-1-one

Jasinski, J.P.; Butcher, R.J.; Mustafa Khaleel, V.; Sarojini, B.K.; Yathirajan, H.S.

doi:10.1107/S1600536811007598

Volume 67
Part 4
Page o795
April 2011

Received 3 February 2011
Accepted 28 February 2011
Online 5 March 2011

Key indicators
Single-crystal X-ray study
T = 110 K
Mean (C-C) = 0.002 Å
R = 0.046
wR = 0.134
Data-to-parameter ratio = 14.1
Details

(2E)-3-(2-Anthracen-2-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one

Jerry P. Jasinski,^a ^* Ray J. Butcher,^b V. Musthafa Khaleel,^c B. K. Sarojini ^d and H. S. Yathirajan ^d

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,^cDepartment of Chemistry, P.A. College of Engineering, Mangalore, 574 153, India, and ^dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
Correspondence e-mail: jjasinski@keene.edu

The asymmetric unit of the title compound, C₂₃H₁₆O₂, contains two independent molecules in which the dihedral angles between the anthracene ring system and the benzene ring are 73.0 (3) and 73.3 (3)°. In both independent molecules, the hydroxy group is involved in an intramolecular O-HO hydrogen bond. The crystal packing is stabilized by [pi] - [pi] interactions [centroid-centroid distances = 3.6518 (9), 3.7070 (9) and 3.7632 (9) Å] and weak intermolecular C-HO hydrogen bonds.

Related literature

For related structures, see: Chantrapromma et al. (2009); Jasinski et al. (2010, 2011a,b); Lu et al. (2009); Suwunwong et al. (2009); Wang et al. (2009, 2010).

Experimental

Crystal data

C₂₃H₁₆O₂
M_r = 324.36
Monoclinic, P 2₁ /c
a = 14.0748 (5) Å
b = 13.7362 (5) Å
c = 16.9800 (8) Å
= 101.487 (5)°
V = 3217.1 (2) Å³
Z = 8
Cu K radiation
= 0.67 mm^-1
T = 110 K
0.46 × 0.35 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.530, T_max = 1.000
14048 measured reflections
6371 independent reflections
5277 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.134
S = 1.06
6371 reflections
453 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1A-H1AO2A	0.84	1.83	2.5729 (15)	146
O1B-H1BO2B	0.84	1.80	2.5452 (16)	146
C14B-H14BO1Bⁱ	0.95	2.60	3.537 (2)	169
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5048 ).

Acknowledgements

VMK thanks P. A. College of Engineering for the research facilities. HSY thanks the UOM for sabbatical leave. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

Chantrapromma, S., Horkaew, J., Suwunwong, T. & Fun, H.-K. (2009). Acta Cryst. E65, o2673-o2674.
Jasinski, J. P., Butcher, R. J., Chidan Kumar, C. S., Yathirajan, H. S. & Mayekar, A. N. (2010). Acta Cryst. E66, o2936-o2937.
Jasinski, J. P., Butcher, R. J., Siddaraju, B. P., Narayana, B. & Yathirajan, H. S. (2011a). Acta Cryst. E67, o313-o314.
Jasinski, J. P., Butcher, R. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011b). Acta Cryst. E67, o352-o353.
Lu, Y.-H., Wang, G.-Z., Zhou, C.-H. & Zhang, Y.-Y. (2009). Acta Cryst. E65, o1396.
Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Suwunwong, T., Chantrapromma, S., Karalai, C., Pakdeevanich, P. & Fun, H.-K. (2009). Acta Cryst. E65, o420-o421.
Wang, G.-Z., Fang, B. & Zhou, C.-H. (2009). Acta Cryst. E65, o2619.
Wang, X.-L., Wang, G.-Z., Geng, R.-X. & Zhou, C.-H. (2010). Acta Cryst. E66, o320.

organic compounds