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

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

doi:10.1107/S1600536809019436

. 2009 May 29;65(Pt 6):o1439–o1440. doi: 10.1107/S1600536809019436

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

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

PMCID: PMC2969694 PMID: 21583279

Abstract

In the title compound, C₂₁H₂₄O₃, the enone group adopts an s–cis conformation. The planes of the aromatic rings are inclined at an angle of 6.1 (1)°. The alkoxy tail is not linear, with the maximum deviation from the least-squares plane being 0.375 (2) Å. Molecules are connected into extended chains along the a axis through O—H⋯O_carbonyl hydrogen bonds and are interlinked via C—H⋯O interactions to form a two-dimensional array parallel to the ab plane.

Related literature

For the biological properties of chalcone derivatives, see: Bhat et al. (2005 ▶); Xue et al. (2004 ▶); Zhao et al. (2005 ▶); Satyanarayana et al. (2004 ▶); Won et al. (2005 ▶). For related structures, see: Razak et al. (2009 ▶); Razak et al. (2009a ▶,b ▶); Ngaini, Fadzillah et al. (2009 ▶); Ngaini, Rahman et al. (2009 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₁H₂₄O₃
M _r = 324.40
Orthorhombic,
a = 10.0237 (2) Å
b = 9.7695 (2) Å
c = 35.3220 (6) Å
V = 3458.96 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.25 × 0.12 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.980, T _max = 0.995
25370 measured reflections
5659 independent reflections
3311 reflections with I > 2σ(I)
R _int = 0.086

Refinement

R[F ² > 2σ(F ²)] = 0.073
wR(F ²) = 0.139
S = 1.02
5659 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.25 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/S1600536809019436/tk2457sup1.cif

e-65-o1439-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019436/tk2457Isup2.hkl

e-65-o1439-Isup2.hkl^{(277.2KB, 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⋯O2ⁱ	0.89 (3)	1.77 (3)	2.6466 (19)	169 (2)
C1—H1A⋯O1ⁱⁱ	0.93	2.55	3.458 (2)	164

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

Acknowledgments

HKF and IAR thank the Malaysian Government and Universiti Sains Malaysia for a Science Fund grant (No. 305/PFIZIK/613312) and a Research University Golden Goose grant (No. 1001/PFIZIK/811012). ZN and HH thank Universiti Malaysia Sarawak for a 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

Chalcones derivatives are reported to demonstrate 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) as well as anti-hyperglycemic (Satyanarayana et al., 2004) activities. Synthetic and naturally occurring chalcones have been extensively studied and developed as pharmaceutically important molecules. As part of our studies, we have synthesized the title chalcone derivative, (I), and tested its anti-bacterial activity against E. coli ATCC 8739; the compound showed anti-microbial activity. In this paper, we report the crystal structure of (I).

The conformation of the enone (O2/C7–C9) moiety in (I) is s–cis with the O2—C7—C8—C9 torsion angle being 5.7 (3)°. The mean plane through the enone moiety makes dihedral angles of 15.9 (1)° and 10.9 (1)°, with the C1–C6 and C10–C15 aromatic rings, respectively. The two aromatic rings form a dihedral angle of 6.1 (1)°.

The short H1A···H8A (2.16 Å) contact resulted in the slight widening of the C1—C6—C7 (123.0 (2)°) and C6—C7—C8 (120.7 (2)°) angles whereas the widening of C8—C9—C10 and C9—C10—C15 angles to 129.0 (2)° and 123.7 (2)° respectively, resulted from the close interatomic contact of H8A···H15A (2.34 Å). Correspondingly, the opening of the O3—C13—C12 (124.9 (2)°) angle is the consequence of strain induced by short H12A···H16A (2.28 Å) and H12A···H16B (2.38 Å) contacts. Similar features can also be found in previously reported related structures (Razak et al., 2009; Razak et al., 2009a,b; Ngaini, Fadzillah et al., 2009; Ngaini, Rahman et al., 2009).

Even though the C16—O3—C13—C12 torsion angle is 0.8 (3)°, only part of the alkoxyl tail, O3/C16–C18, is co-planar with the attached aromatic ring [maximum deviation of the least-squares plane of O3/C16–C18 is -0.002 (2) Å]. The alkoxyl chain is twisted about the C19—C20 bond as shown by the C18—C19—C20—C21 torsion angle being -73.4 (2)°. The least-squares plane through the the alkoxyl chain, O3/C16–C21, [maximum deviation of 0.375 (2) Å at C16] makes a dihedral angle of 49.1 (2)° with the attached aromatic ring.

In the crystal structure, intermolecular O1—H1O1···O2 hydrogen bonds between the hydroxy and keto groups link the molecules into extended chains along the a axis, Table 1. The chains are interlinked via C1—H1A···O1 interactions into a 2-D array parallel to the ab-plane, Table 1 and Fig. 2.

Experimental

A mixture of 4-hydroxyacetophenone (1.36 g, 10 mmol), 4-hexyloxybenzaldehyde (2.06 ml, 10 mmol) and KOH (2.02 g, 36 mmol) in methanol (30 ml) 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 a hexane–ethanol (7:1) solution, followed by few days of slow evaporation, crystals were collected.