(E)-3-(4-Decyl­oxyphen­yl)-1-(2-hydroxy­phen­yl)prop-2-en-1-one

Zainab Ngaini; Norashikin Irdawaty Abd Rahman; Hasnain Hussain; Ibrahim Abdul Razak; Hoong-Kun Fun

doi:10.1107/S1600536809010848

. 2009 Mar 28;65(Pt 4):o889–o890. doi: 10.1107/S1600536809010848

(E)-3-(4-Decyloxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one

Zainab Ngaini ^a, Norashikin Irdawaty Abd Rahman ^a, Hasnain Hussain ^b, Ibrahim Abdul Razak ^c,^*,^‡, Hoong-Kun Fun ^c,^§

PMCID: PMC2968804 PMID: 21582598

Abstract

In the title compound, C₂₅H₃₂O₃, the enone group is in an s–cis configuration. The dihedral angle between the benzene rings is 8.84 (7)°. An intramolecular O—H⋯O interaction between the keto and hydroxy groups forms an S(6) ring motif. Intermolecular C—H⋯O interactions link the molecules into supramolecular chains along the c axis which are subsequently stacked down the b axis; the crystal structure is further consolidated by C—H⋯π interactions.

Related literature

For general background, see: Bhat et al. (2005 ▶); Xue et al. (2004 ▶); Satyanarayana et al. (2004 ▶); Won et al. (2005 ▶); Zhao et al. (2005 ▶). For related structures, see: Ng, Razak et al. (2006 ▶); Ng, Patil et al. (2006 ▶); Razak et al. (2009 ▶); Ngaini et al. (2009 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, 1986 ▶.

Experimental

Crystal data

C₂₅H₃₂O₃
M _r = 380.51
Monoclinic,
a = 21.2700 (4) Å
b = 7.6779 (2) Å
c = 13.2330 (3) Å
β = 101.720 (1)°
V = 2116.01 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.44 × 0.28 × 0.04 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.967, T _max = 0.997
25687 measured reflections
6221 independent reflections
4014 reflections with I > 2σ(I)
R _int = 0.056

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.165
S = 1.04
6221 reflections
258 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010848/tk2402sup1.cif

e-65-0o889-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010848/tk2402Isup2.hkl

e-65-0o889-Isup2.hkl^{(304.5KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.91 (2)	1.68 (2)	2.526 (2)	152 (2)
C15—H15A⋯O3ⁱ	0.93	2.48	3.406 (2)	174
C20—H20B⋯Cg1ⁱⁱ	0.97	2.85	3.702 (2)	147
C22—H22A⋯Cg1ⁱⁱⁱ	0.97	2.84	3.712 (2)	149
C16—H16A⋯Cg2ⁱⁱⁱ	0.97	2.87	3.596 (2)	132

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

Acknowledgments

HKF and IAR thank the Malaysian Government and Universiti Sains Malaysia for the award of the Science Fund grant No. 305/PFIZIK/613312 and for the Research University Golden Goose grant No. 1001/PFIZIK/811012. ZN and HH thank Universiti Malaysia Sarawak for the Geran Penyelidikan Dana Khas Inovasi, grant No. DI/01/2007(01). NIAR thanks the Malaysian Government and Universiti Malaysia Sarawak for providing a scholarship for postgraduate studies.

supplementary crystallographic information

Comment

Chalcone is one of the important intermediates in the biosynthesis of flavonoid. Chalcones derivatives are reported to exhibit biological properties such as an anti-malarial (Xue et al., 2004), anti-cancer (Bhat et al., 2005), anti-inflammatory (Won et al., 2005), anti-platelet (Zhao et al., 2005), and as well as anti-hyperglycemic (Satyanarayana et al., 2004) activities.

Chalcone derivatives possessing alkyl chains of varying length have been synthesized in our laboratory. They were tested against E. coli ATCC 8739 for their anti-bacterial activities and showed anti-microbial activity. In this paper, we report the structure of one of the chalcone derivatives mentioned above.

In (I), Fig. 1, the enone group is in an s-cis configuration as indicated by the torsion angle O2—C7—C8—C9 of 1.2 (2)°. The least-square plane through the enone moiety makes dihedral angle of 3.64 (10)° with C1—C6 benzene ring whereas the dihedral angle formed with the C10—C15 benzene ring is 7.72 (10)°. The dihedral angle between these benzene rings is 8.84 (7)°. The alkoxyl group is co-planar with the attached benzene ring as shown by the torsion angle C16—O3—C13—C14 of -1.6 (2)°.

The strain induced by a short H5A···H8A contact (2.11 Å) leads to the slight opening of the C5—C6—C7 angle to 123.03 (13)°. Likewise, the widening of C8—C9—C10 (128.65 (14)°) and C9—C10—C11 (123.18 (13)°) angles are the result of a close H8A···H11A (2.32 Å) interatomic contact. These features were also observed in related structures reported previously (Ng, Razak et al., 2006; Ng, Patil et al., 2006; Razak et al., 2009; Ngaini et al., 2009). An intramolecular O1-H1O1···O2 interaction between the keto group and the hydroxy generates an S(6) ring motif (Bernstein et al., 1995).

In the crystal structure, C15—H15A···O3 (x, -y + 1/2, z + 1/2) intermolecular interactions link the molecules into extended chains along the c axis (Table 1 and Fig. 2). These chains are subsequently stacked down the b axis. The crystal packing is further stabilized by the presence of C—H···π interactions formed between atoms C16, C20 and C22 in the alkoxyl tail and the benzene rings (Table 1).

Experimental

A mixture of 2-hydroxyacetophenone (2.72 ml, 20 mmol), 4-decyloxybenzaldehyde (5.25 ml, 20 mmol) and KOH (4.04 g, 72 mmol) in methanol (60 ml) was heated at reflux for 10 h. The reaction mixture was cooled to room temperature and acidified with cold diluted HCl (2 N). The resulting precipitate was filtered, washed and dried. After redissolving in hexane and followed by few days of slow evaporation, crystals were collected.