(2E)-2-Benzyl­idene-5,6-dimethoxy­indan-1-one

Mohamed Ashraf Ali; Rusli Ismail; Soo Choon Tan; Chin Sing Yeap; Hoong-Kun Fun

doi:10.1107/S1600536810035695

. 2010 Sep 11;66(Pt 10):o2531–o2532. doi: 10.1107/S1600536810035695

(2E)-2-Benzylidene-5,6-dimethoxyindan-1-one

Mohamed Ashraf Ali ^a, Rusli Ismail ^a, Soo Choon Tan ^a, Chin Sing Yeap ^b,^‡, Hoong-Kun Fun ^b,^*,^§

PMCID: PMC2983266 PMID: 21587524

Abstract

The molecular structure of the title compound, C₁₈H₁₆O₃, is roughly planar; the maximum deviation of the indanone ring system is 0.027 (1) Å and it makes a dihedral angle of 2.69 (3)° with the phenyl ring. The torsion angles between the two methoxy groups and the indanone ring are −14.67 (11) and −1.11 (12)°. In the crystal, molecules are connected into a ribbon along the a axis via weak intermolecular C—H⋯O hydrogen bonds. Weak intermolecular C—H⋯π and π–π [centroid–centroid distance = 3.7086 (6) Å] interactions are also observed.

Related literature

For general background to and the biological activity of chalcone derivatives, see: Boumendjel et al. (2009 ▶); D’Archivio et al. (2008 ▶); Dicarlo et al. (1999 ▶); Echeverria et al. (2009 ▶); Heidenreich et al. (2008 ▶); Katsori & Hadjipavlou-Latina (2009 ▶); Miranda et al. (1999 ▶); Nowakowska (2007 ▶); Shah et al. (2008 ▶); Syed et al. (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₈H₁₆O₃
M _r = 280.31
Monoclinic,
a = 6.0209 (6) Å
b = 14.8550 (14) Å
c = 15.2292 (15) Å
β = 90.603 (2)°
V = 1362.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.44 × 0.29 × 0.16 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.960, T _max = 0.985
31475 measured reflections
6003 independent reflections
4902 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.130
S = 1.09
6003 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.58 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035695/is2598sup1.cif

e-66-o2531-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035695/is2598Isup2.hkl

e-66-o2531-Isup2.hkl^{(293.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O3ⁱ	0.96	2.53	3.4107 (11)	152
C18—H18B⋯O2ⁱⁱ	0.96	2.58	3.5320 (11)	173
C16—H16A⋯Cg1ⁱⁱⁱ	0.93	2.99	3.7224 (9)	137

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

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

supplementary crystallographic information

Comment

Chalcones have been reported to possess antiinflammatory, antimicrobial, antioxidant and anticancer properties (Echeverria et al., 2009; Nowakowska, 2007; Miranda et al., 1999; Shah et al., 2008; Boumendjel et al., 2009; Katsori & Hadjipavlou-Latina, 2009). Chalcones are one of the major classes of natural products with widespread distribution in spices, tea, beer, fruits and vegetables. They have been recently subjects of great interest for their pharmacological activities (Dicarlo et al., 1999). Prostate cancer is one of the most commonly diagnosed cancers in men and the second leading cause of cancer deaths in the European Union and United States of America (Heidenreich et al., 2008). Many antitumor drugs have been developed for prostate cancer patients, but their intolerable systemic toxicity often limits their clinical use. Chemoprevention is one of the most promising approaches in prostate cancer research, in which natural or synthetic agents are used to prevent this malignant disease (Heidenreich et al., 2008; Syed et al., 2008; D'Archivio et al., 2008).

The molecular structure of the title compound is essentially coplanar (Fig. 1). The maximum deviation of the indanone group is 0.027 (1) Å and it makes dihedral angle of 2.69 (3)° with the phenyl ring [C11–C16]. The torsion angles of the two methoxy groups are [C17–O2–C4–C5] 165.99 (7) and [C18–O3–C5–C4] 179.19 (7)°.

In the crystal structure, intermolecular C17—H17A···O3 hydrogen bonds (Table 1) link the molecules into dimers (Fig. 2). These dimers are interconnected into ribbons propagating along the [100] direction via intermolecular C18—H18B···O2 hydrogen bonds (Fig. 2, Table 1). Weak intermolecular C—H···π (Table 1) and π–π interactions are also observed. [Cg1···Cg2^iv of 3.7086 (6) Å; (iv) 1 - x, 1 - y, -z. Cg1 and Cg2 are the centroids of C2–C7 and C11–C16 benzene ring.]

Experimental

A mixture of 5,6-dimethoxyindan-1-one (0.001 mmol) and benzaldehyde (0.001 mmol) were dissolved in methanol (10 ml) and 30% sodium hydroxide solution (5 ml) was added and stirred for 5 h. After completion of the reaction as evident from TLC, the mixture was poured into crushed ice then neutralized with concentrated HCl. The precipitated solid was filtered, washed with water and recrystallized from ethanol to reveal the title compound as light yellow crystals.