(Z)-3-(Anthracen-9-yl)-1-(2-eth­oxy­phen­yl)prop-2-en-1-oneThis paper is dedicated to the late His Royal Highness Prince Mahidol of Songkla for his contributions to the development of medical education in Thailand on the occasion of Mahidol Day which falls on the 24th September.

Joothamongkhon, J.; Chantrapromma, S.; Kobkeatthawin, T.; Fun, H.-K.

doi:10.1107/S1600536810038183

Volume 66
Part 10
Pages o2669-o2670
October 2010

Received 14 September 2010
Accepted 24 September 2010
Online 30 September 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.102
Data-to-parameter ratio = 13.0
Details

(Z)-3-(Anthracen-9-yl)-1-(2-ethoxyphenyl)prop-2-en-1-one¹

Jaruwan Joothamongkhon,^a Suchada Chantrapromma,^a ^*⁺ Thawanrat Kobkeatthawin ^a and Hoong-Kun Fun ^b ⁺⁺

^aCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: suchada.c@psu.ac.th

The molecule of the title chalcone, C₂₅H₂₀O₂, consisting of 2-ethoxyphenyl and anthracene rings bridged by a prop-2-en-1-one unit, is twisted and exists in the Z configuration with respect to the central C=C bond. The dihedral angle between the benzene and anthracene rings is 78.17 (9)°. The propene unit makes dihedral angles of 44.5 (2) and 81.1 (2)° with the benzene and anthracene rings, respectively. The ethoxy substituent is almost coplanar with the attached benzene ring [C-O-C-C torsion angle = 178.57 (19)°]. In the crystal, molecules are linked into chains along the a axis by weak C-HO interactions. The crystal structure is further stabilized by C-H [pi] interactions.

Related literature

For bond-length data, see: Allen et al. (1987). For related structures, see: Chantrapromma et al. (2009, 2010); Suwunwong et al. (2009). For background to and applications of chalcones, see: Kobkeatthawin et al. (2010); Nowakowska (2007); Oliveira et al. (2007); Patil & Dharmaprakash (2008); Saydam et al. (2003); Svetlichny et al. (2007); Tewtrakul et al. (2003). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986).

Experimental

Crystal data

C₂₅H₂₀O₂
M_r = 352.41
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.4442 (1) Å
b = 10.7665 (2) Å
c = 32.2160 (7) Å
V = 1888.34 (6) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 100 K
0.47 × 0.16 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.964, T_max = 0.995
18936 measured reflections
3190 independent reflections
2632 reflections with I > 2(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.102
S = 1.04
3190 reflections
245 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C10-C11/C16-C18/C23 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C3-H3AO1ⁱ	0.93	2.59	3.205 (3)	124
C8-H8AO1ⁱⁱ	0.93	2.35	3.093 (2)	136
C9-H9ACg2ⁱⁱ	0.93	2.88	3.7609 (19)	160
C24-H24ACg1ⁱⁱ	0.97	2.86	3.739 (2)	151
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2490 ).

Acknowledgements

JJ thanks the Development and Promotion of Science and Technology Talents Project (DPST) for a study grant. The authors thank the Prince of Songkla University for financial support and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

References

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