(E)-2-(3,4-Dimeth­oxy­benzyl­idene)-5,6-dimeth­oxy-2,3-dihydro-1H-inden-1-one

Ali, M.A.; Ismail, R.; Tan, S.C.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536810041619

Volume 66
Part 11
Page o2875
November 2010

Received 14 October 2010
Accepted 15 October 2010
Online 20 October 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R = 0.043
wR = 0.124
Data-to-parameter ratio = 24.1
Details

(E)-2-(3,4-Dimethoxybenzylidene)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Mohamed Ashraf Ali,^a Rusli Ismail,^a Soo Choon Tan,^a Ching Kheng Quah ^b ⁺ and Hoong-Kun Fun ^b ^*⁺⁺

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound, C₂₀H₂₀O₅, the 2,3-dihydro-1H-indene ring system is essentially planar [maximum deviation = 0.010 (1) Å] and is inclined at an angle of 4.09 (4)° with respect to the phenyl ring. The C=C bond has an E configuration. In the crystal, the molecules are linked into chains propagating in [102] via intermolecular C-HO hydrogen bonds. The crystal structure is further consolidated by C-H [pi] interactions.

Related literature

For general background to and the biological activity of chalcones, see: Nielsen et al. (1998); Go et al. (2005); Nowakowska (2007); Furusawa et al. (2005). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₂₀H₂₀O₅
M_r = 340.36
Monoclinic, P 2₁ /c
a = 7.7991 (7) Å
b = 7.2595 (6) Å
c = 29.589 (2) Å
= 101.977 (3)°
V = 1638.8 (2) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 100 K
0.53 × 0.45 × 0.09 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.950, T_max = 0.992
19303 measured reflections
5535 independent reflections
4471 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.124
S = 1.04
5535 reflections
230 parameters
H-atom parameters constrained
_max = 0.48 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the cetroid of C2-C7 benzene ring.

D-HA	D-H	HA	DA	D-HA
C18-H18AO4ⁱ	0.96	2.34	3.0939 (13)	135
C1-H1ACg1ⁱⁱ	0.97	2.64	3.4804 (11)	146
Symmetry codes: (i) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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: HB5680 ).

Acknowledgements

The authors wish to express their thanks to Universiti Sains Malysia (USM) for providing research facilities. HKF and CKQ also thank USM for the Research University Grant (No. 1001/PFIZIK/811160). CKQ also thanks USM for the award of a USM fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Furusawa, M., Tanaka, T., Ito, T., Nishikawa, A., Yamazaki, N., Nakaya, K., Matsuura, N., Tsuchiya, H., Nagayama, M. & Iinuma, M. (2005). J. Health Sci. 51, 376-378.
Go, M. L., Wu, X. & Liu, X. L. (2005). Curr. Med. Chem. 12, 483-499.
Nielsen, S. B., Christensen, S. F., Cruciani, G. & Kharazmi, A. (1998). J. Med. Chem. 41, 4819-4832
Nowakowska, Z. (2007). Eur. J. Med. Chem. 42, 125-137.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds