(E)-1-(3-Hy­droxy­phen­yl)-3-[4-(tetra­dec­yl­oxy)phen­yl]prop-2-en-1-one

Siti Muhaini Haris Fadzillah; Zainab Ngaini; Hasnain Hussain; Ibrahim Abdul Razak; Safra Izuani Jama Asik

doi:10.1107/S1600536812038020

. 2012 Sep 8;68(Pt 10):o2911–o2912. doi: 10.1107/S1600536812038020

(E)-1-(3-Hydroxyphenyl)-3-[4-(tetradecyloxy)phenyl]prop-2-en-1-one

Siti Muhaini Haris Fadzillah ^a, Zainab Ngaini ^a, Hasnain Hussain ^b, Ibrahim Abdul Razak ^c,^*,^‡, Safra Izuani Jama Asik ^c

PMCID: PMC3470259 PMID: 23125703

Abstract

In the title compound, C₂₉H₄₀O₃, the enone moiety adopts an s-cis conformation. The dihedral angle between the benzene rings is 4.33 (5)° The least-squares mean line through the tetradecyl side chain forms a dihedral angle of 83.99 (7)° with the normal to the attached benzene ring. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds involving the keto and the hydroxy O atoms form ribbons along [-41-1]. The crystal structure also features C—H⋯π interactions.

Related literature

For the biological properties of chalcone derivatives, see: Bhat et al. (2005 ▶); Xue et al. (2004 ▶); Won et al. (2005 ▶); Zhao et al. (2005 ▶); Satyanarayana et al. (2004 ▶). For related structures, see: Razak et al. (2009 ▶); Ngaini et al. (2010 ▶, 2011 ▶). 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

C₂₉H₄₀O₃
M _r = 436.61
Triclinic,
a = 6.5138 (16) Å
b = 10.155 (2) Å
c = 19.264 (5) Å
α = 75.361 (6)°
β = 85.872 (7)°
γ = 83.013 (6)°
V = 1222.6 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.29 × 0.12 × 0.08 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.979, T _max = 0.994
26295 measured reflections
7155 independent reflections
5052 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.147
S = 0.95
7155 reflections
293 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT (Bruker, 2009 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812038020/rz5001sup1.cif

e-68-o2911-sup1.cif^{(33.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038020/rz5001Isup2.hkl

e-68-o2911-Isup2.hkl^{(350.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812038020/rz5001Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the C10–C15 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2ⁱ	0.93 (2)	1.80 (2)	2.7269 (14)	175.6 (18)
C29—H29A⋯O1ⁱⁱ	0.96	2.44	3.3589 (18)	160
C17—H17B⋯Cg1ⁱⁱⁱ	0.97	2.73	3.6159 (16)	152
C28—H28A⋯Cg2^iv	0.97	2.93	3.8481 (16)	159

Open in a new tab

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

Acknowledgments

IAR and SIJA thank the Malaysian Government and Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS) No. 203/PFIZIK/6711171. ZN and HH thank Universiti Malaysia Sarawak and the Ministry of Science, Technology and Innovation (MOSTI), for financing this project through FRGS/01(14)/743/2010 (29). SMHF thanks the Malaysian Government and Universiti Malaysia Sarawak for providing a scholarship for postgraduate studies.

supplementary crystallographic information

Comment

Chalcones are highly reactive subtances of varied nature. They have been reported to possess many useful properties including 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 anti-hyperglynemic (Satyanarayana et al., 2004) activities. Herein, we report the crystal structure of the title compound (Fig. 1).

The enone moiety (O2/C7–C9) adopts an s-cis conformation with the O2–C7–C8–C9 torsion angle of 0.64 (17)°. The dihedral angles between the least-square plane through the enone moiety and the benzene rings (C1–C6 and C10–C15) are 6.26 (7) and 4.65 (7)°, respectively. The dihedral angle between these benzene rings is 4.33 (5)°. The bond lengths observed in the title compound are comparable with the values previously reported values in the literature (Allen et al., 1987).

The short H8A···H15A (2.20 Å) and H8A···H1A (2.11 Å) contacts results in the widening of C8–C9–C10 (126.84 (11)°) and C1–C6–C7 (123.31 (10)°) angles, respectively. The geometric parameters are consistent to those observed in closely related structures (Razak et al., 2009; Ngaini et al., 2010; Ngaini et al., 2011).

The conformation throughout the zigzag alkoxyl tail is trans and is roughly coplanar with the attached benzene (C10–C15) ring as the torsion angle C16–O3–C13–C14 is 176.57 (10)°. However, only the aliphatic part (C16–C29) of the alkoxyl tail is constantly within the zigzag plane. The torsion angle of the aliphatic part deviate from the ideal value by 0.02 (10)–3.75 (10)° while the O3–C16–C17–C18 torsion angle shows value of 173.64 (9)°.

In the crystal packing (Fig. 2), the molecules are arranged in head-to-tail manner along the [-4 1 -1] direction. This arrangement is linked into extended chains through C29—H29···O1 intermolecular interactions. These chains are alternately interconnected by O1—H1O1···O2 intermolecuar hydrogen bonds. Furthermore, the crystal packing is stabilized by weak C—H···π interactions (Table 1) with the distance of 3.6159 (16) and 3.8481 (16) Å.

Experimental

A mixture of 3-hydroxyacetophenone (1.36 g, 10 mmol) and 4-tetradecyloxybenzaldehyde (3.19 ml, 10 mmol) in methanol (40 ml) was heated at reflux for 12 h. The reaction was cooled to room temperature and acidified with cold diluted HCl (2N). The resulting precipitate was filtered, washed and dried. After redissolving in hexane-ethanol (7:1 v/v) followed by few days of slow evaporation, crystals were collected.