(E)-1-[4-(Hex­yloxy)phen­yl]-3-(4-hy­droxy­phen­yl)prop-2-en-1-one

Zainab Ngaini; Siti Muhaini Haris Fadzillah; Hasnain Hussain; Ibrahim Abdul Razak; Hoong-Kun Fun

doi:10.1107/S1600536810052086

. 2010 Dec 18;67(Pt 1):o169–o170. doi: 10.1107/S1600536810052086

(E)-1-[4-(Hexyloxy)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one

Zainab Ngaini ^a, Siti Muhaini Haris Fadzillah ^a, Hasnain Hussain ^b, Ibrahim Abdul Razak ^c,^*,^‡, Hoong-Kun Fun ^c,^§

PMCID: PMC3050273 PMID: 21522676

Abstract

In the title compound, C₂₁H₂₄O₃, intermolecular O—H⋯O and C—H⋯O interactions form bifurcated acceptor bonds, generating R ₂ ¹(6) ring motifs. These ring motifs link the molecules into extended chains along [010]. The crystal structure is further stabilized by C—H⋯π interactions.

Related literature

For the biological properties of chalcone derivatives, see: Bhat et al. (2005 ▶); Xue et al. (2004 ▶); Zhao et al. (2005 ▶); Lee et al. (2006 ▶). For related structures, see: Razak et al. (2009 ▶, 2009a ▶,b ▶); Ngaini, Fadzillah et al. (2009 ▶); Ngaini, Rahman 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 ▶). For bond-length data, see: Allen et al. (1987) ▶.

Experimental

Crystal data

C₂₁H₂₄O₃
M _r = 324.40
Monoclinic,
a = 10.2807 (2) Å
b = 16.6322 (2) Å
c = 11.4736 (2) Å
β = 113.439 (1)°
V = 1799.99 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.53 × 0.46 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.960, T _max = 0.993
35735 measured reflections
5839 independent reflections
4743 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.135
S = 1.03
5839 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.20 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/S1600536810052086/fj2369sup1.cif

e-67-0o169-sup1.cif^{(21KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052086/fj2369Isup2.hkl

e-67-0o169-Isup2.hkl^{(285.9KB, hkl)}

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

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

Cg2 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.84	1.86	2.694 (1)	175
C4—H4A⋯O1ⁱ	0.95	2.54	3.213 (1)	128
C16—H16A⋯Cg2ⁱⁱ	0.99	2.77	3.666 (1)	151

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

Acknowledgments

HKF and IAR thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No.1001/PFIZIK/811151. ZN and HH thank Universiti Malaysia Sarawak for the Geran Penyelidikan Dana Khas Inovasi, grant No. DI/01/2007 (01). SMHF thanks the Malaysian Government and Universiti Malaysia Sarawak for providing a scholarship for her postgraduate studies.

supplementary crystallographic information

Comment

The biological properties of chalcones derivatives have been extensively reported (Bhat et al., 2005; Xue et al., 2004; Lee et al., 2006; Zhao et al., 2005). Synthetic and naturally occurring chalcones have been widely studied and developed as one of the pharmaceutically important molecules. We have synthesized the title chalcone derivative, (I) which showed antimicrobial activity when tested against E. coli ATCC 8739 In this paper, we report the crystal structure of the title compound.

The bond lengths observed in the title compound (Fig.1) are comparable with previously reported values (Allen et al., 1987). The conformation of the enone moiety (O1/C7—C9) is s-cis as shown by the value of -6.3 (2)° for O1—C9—C8—C7 torsion angle. The enone (O1/C7—C9) moiety adopts s-cis conformation with O2—C7—C8—C9 torsion angle being -6.3 (2)°. The dihedral angle between the mean plane through the enone moiety and the benzene rings is 5.1 (1)° for C1—C6 ring and 5.6 (1)° for C10—C15 ring. The two benzene rings make a dihedral angle of 7.8 (1)° between them.

The widening of C1—C6—C7 and C6—C7—C8 angles to 123.0 (1)° and 126.9 (1)° respectively, are the consequences of the close interatomic contact between H1A and H8A which is 2.20 Å. Similarly, the strain induced by short H8A···H11A contact, which is 2.09Å resulted in the opening of C9—C10—C11 angle to 123.8 (1)°. The distortion of angles, which is relative to what is predicted in terms of hybidization principles can also be observed in the related structures previously reported by Razak, Fun, Ngaini, Rahman et al. (2009), Razak, Fun, Ngaini, Fadzillah et al. (2009a,b), Ngaini, Fadzillah et al. (2009) and Ngaini, Rahman et al. (2009).

The conformation assumed by the zigzag alkoxyl tail is trans. Even though the torsion angle of C12—C13—O3—C16 is -1.3 (2)°, which shows that it is roughly coplanar with the attached benzene ring, the alkoxyl tail is actually twisted about the C18—C19 bond. Within the aliphatic chain, the C17—C18—C19—C20 torsion angle shows the value of -167.0 (1)°

In the crystal structure, intermolecular O2—H2···O1(-x,y - 1/2,-z + 3/2) and C4—H4A···O1(-x,y - 1/2,-z + 3/2) interactions form bifurcated acceptor bonds generating R¹₂(6) ring motifs (Bernstein et al., 1995). These intermolecular interactions link the molecules into extended chains along the [0 1 0] direction. The crystal structure is further stabilized by C—H···π interactions (Table 1).

Experimental

A mixture of 4-hydroxybenzaldehyde (1.22 g, 10 mmol), 4-hexyloxyacetophenone (2.20 g, 10 mmol) and KOH (2.02 g, 36 mmol) in 30 ml of methanol was heated at reflux for 24 h. The reaction 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-ethanol mixture, followed by few days of slow evaporation, suitable crystals were collected for X-ray analysis.