Ethyl (E)-3-(anthracen-9-yl)prop-2-enoate

Bugenhagen, B.; Al Jasem, Y.; Hindawi, B. al; Al Rawashdeh, N.; Thiemann, T.

doi:10.1107/S1600536812051033

Volume 69
Part 1
Pages o130-o131
January 2013

Received 9 December 2012
Accepted 17 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.004 Å
R = 0.057
wR = 0.171
Data-to-parameter ratio = 12.9
Details

Ethyl (E)-3-(anthracen-9-yl)prop-2-enoate

Bernhard Bugenhagen,^a Yosef Al Jasem,^b Bassam al Hindawi,^c Nathir Al Rawashdeh ^c and Thies Thiemann ^c ^*

^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 asymmetric unit of the title compound, C₁₉H₁₆O₂, there are two symmetry-independent molecules (A and B) that differ in the conformation of the ester ethoxy group. In the crystal, the molecules form inversion dimers via pairs of C-HO interactions. Within the dimers, the anthracenyl units have interplanar distances of 0.528 (2) and 0.479 (2) Å for dimers of molecules A and B, respectively. Another short C-HO contact between symmetry-independent dimers links them into columns parallel to [10-1]. These columns are arranged into (111) layers and there are [pi] - [pi] stacking interactions [centroid-centroid distances = 3.6446 (15) and 3.6531 (15) Å] between the anthracenyl units from the neighbouring columns. In addition, there are C-H [pi] interactions between the anthracenyl unit of dimers A and dimers B within the same column.

Related literature

For an analogous preparation of the title compound, see: Nguyen & Weizman (2007). For modeling of the title compound at the B3LYP/6-31G* level, see: Coleman (2007). For crystal structures of photodimerizable arylenes, see: Vishnumurthy et al. (2002); Mascitti & Corey (2006); Sonoda (2011); Schmidt (1964). For the photodimerization of anthracenes in the crystal, see: Schmidt (1971); Ihmels et al. (2000).

Experimental

Crystal data

C₁₉H₁₆O₂
M_r = 276.32
Triclinic, $[P \overline 1]$
a = 8.8700 (5) Å
b = 12.8918 (7) Å
c = 13.1062 (7) Å
= 84.389 (4)°
= 84.620 (4)°
= 70.771 (5)°
V = 1405.28 (13) Å³
Z = 4
Cu K radiation
= 0.66 mm^-1
T = 291 K
0.22 × 0.11 × 0.09 mm

Data collection

Agilent SuperNova Dual Atlas diffractometer
Absorption correction: Gaussian (CrysAlis PRO; Agilent, 2012) T_min = 0.889, T_max = 0.942
11350 measured reflections
4901 independent reflections
4250 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.171
S = 1.10
4901 reflections
381 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1A/C2A/C7A-C9A/C14A and C2A-C7A rings, respectively.

D-HA	D-H	HA	DA	D-HA
C13A-H13AO1Aⁱ	0.93	2.56	3.455 (3)	163
C18B-H18BO2Aⁱⁱ	0.97	2.56	3.422 (3)	148
C3B-H3BO1Bⁱⁱⁱ	0.93	2.57	3.470 (3)	162
C6A-H6AO2B^iv	0.93	2.67	3.438 (3)	140
C19A-H19EO1B^v	0.96	2.66	3.409 (3)	135
C6B-H6BCg1^vi	0.93	2.81	3.447 (3)	126
C8B-H8BCg2^vi	0.93	2.82	3.439 (3)	124
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x+2, -y+1, -z+1; (iii) -x+2, -y, -z+1; (iv) x, y, z+1; (v) x-1, y+1, z; (vi) -x+1, -y+1, -z+2.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within OLEX2 (Dolomanov et al., 2009); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); 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: GK2545 ).

Acknowledgements

The authors thank the UAEU interdisciplinary grant 31S036 for financial support. They also thank Thirumurugan Prakasam, NYU Abu Dhabi, for the mass spectrometry measurements.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Coleman, W. F. (2007). J. Chem. Educ. 84, 121-121.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Ihmels, H., Leusser, D., Pfeiffer, M. & Stalke, D. (2000). Tetrahedron, 56, 6867-6875.
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.
Mascitti, V. & Corey, E. J. (2006). Tetrahedron Lett. 47, 5879-5882.
Nguyen, K. & Weizman, H. (2007). J. Chem. Educ. 84, 119-121.
Schmidt, G. M. J. (1964). J. Chem. Soc., pp. 2014-2021.
Schmidt, G. M. J. (1971). Pure Appl. Chem., 27, 647-678.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sonoda, Y. (2011). Molecules, 16, 119-148.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Vishnumurthy, K., Guru Row, T. N. & Venkatesan, K. (2002). Photochem. Photobiol. Sci. 1, 427-430.

organic compounds

Ethyl (E)-3-(anthracen-9-yl)prop-2-enoate

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References