(E)-3-(4-Heptyl­oxyphen­yl)-1-phenyl­prop-2-en-1-one

Davia McKoy; Marion A Franks; Zerihun Assefa

doi:10.1107/S1600536813034429

. 2014 Jan 18;70(Pt 2):o163–o164. doi: 10.1107/S1600536813034429

(E)-3-(4-Heptyloxyphenyl)-1-phenylprop-2-en-1-one

Davia McKoy ^a, Marion A Franks ^a,^*, Zerihun Assefa ^a

PMCID: PMC3998321 PMID: 24764882

Abstract

In the title compound, C₂₂H₂₆O₂, the aromatic rings are inclined to one another by 8.39 (9)° and the molecule has an E conformation about the C=C bond. In the crystal, molecules stack head-to-tail along the b-axis direction. They are linked by very weak C—H⋯O contacts, forming C(4) chains along [100]. Two chains are linked by a pair of very weak C—H⋯O contacts, enclosing inversion-dimeric R ₂ ²(8) ring motifs. There are also C—H⋯π interactions present, which link the double-stranded chains, forming a two-dimensional network.

Related literature

For general background to chalcones, see: Uchida et al. (1998 ▶); Indira et al. (2002 ▶); Treadwell (2006 ▶). For their various biological properties, see: Avila et al. (2008 ▶); ElSohly et al. (2001 ▶); Gafner et al. (1996 ▶); Akihisa et al. (2003 ▶); Szliszka et al. (2009 ▶); Xia et al. (2000 ▶); Lahtchev et al. (2008 ▶); Bandgar et al. (2010 ▶). For their enhanced cytotoxicity towards certain cancers, see: Won et al. (2005 ▶). For examples of chalcones with general formula Ar—CH–CH—CO—Ar, with molecular pairing involving π–π interactions and hydrogen-bonding, see: Wang et al. (2005 ▶). For related halogen derivatives, see: Dutkiewicz et al. (2010 ▶); Qiu et al. (2006 ▶). graphic file with name e-70-0o163-scheme1.jpg

Experimental

Crystal data

C₂₂H₂₆O₂
M _r = 322.43
Triclinic,
a = 5.6069 (9) Å
b = 7.7822 (13) Å
c = 22.864 (4) Å
α = 81.101 (5)°
β = 85.571 (5)°
γ = 69.879 (4)°
V = 925.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 200 K
0.50 × 0.26 × 0.16 mm

Data collection

Bruker X2S diffractometer
Absorption correction: multi-scan (SADABS, Bruker, 2005 ▶) T _min = 0.965, T _max = 0.989
5754 measured reflections
3149 independent reflections
2314 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.152
S = 1.09
3149 reflections
322 parameters
All H-atom parameters refined
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 2005 ▶; cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: JMol (Hanson, 2010 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813034429/zp2008sup1.cif

e-70-0o163-sup1.cif^{(24.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034429/zp2008Isup2.hkl

e-70-0o163-Isup2.hkl^{(154.5KB, hkl)}

Click here for additional data file.^{(2.5KB, cdx)}

Supporting information file. DOI: 10.1107/S1600536813034429/zp2008Isup3.cdx

Click here for additional data file.^{(7KB, cml)}

Supporting information file. DOI: 10.1107/S1600536813034429/zp2008Isup4.cml

CCDC reference: http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=978369

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

Cg1 and Cg2 are the centroids of rings C4–C9 and C17–C22, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.99 (2)	2.67 (2)	3.513 (2)	143.3 (12)
C8—H8⋯O2ⁱⁱ	0.95 (2)	2.64 (2)	3.545 (2)	159.3 (13)
C10—H10B⋯Cg1ⁱⁱⁱ	0.98 (2)	2.972 (15)	3.8279 (18)	146.6 (13)
C16—H16A⋯Cg2ⁱⁱⁱ	0.97 (3)	2.97 (2)	3.792 (3)	144.5 (18)

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

Acknowledgments

Support from the National Science Foundation (CHE-0959406) for the purchase of the X-ray diffractometer is gratefully acknowledged.

supplementary crystallographic information

1. Comment

Chalcones along with their derivatives can easily be obtained by means of isolation from natural products or synthesized by classic scientific methods. These compounds are interesting in the medical field because of their antibacterial (Avila et al., 2008), antifungal (ElSohly et al., 2001; Gafner et al., 1996), antitumor (Akihisa et al., 2003; Szliszka et al., 2009; Xia et al., 2000; Lahtchev et al., 2008) and anti-inflammatory properties (Bandgar et al., 2010). These compounds have also shown enhanced cytotoxicity towards certain cancers (Won et al., 2005). Synthetically chalcones are derived through an aldol condensation which involves the reaction between an aromatic aldehyde with an aliphatic aldehyde or ketone in the presence of a strong base (hydroxide or alkoxide). The resulting compound contains two aromatic rings joined by a three carbon α,β-unsaturated carbonyl system, and we report herein on its crystal structure.

The molecular structure of the title molecule is illustrated in Fig. 1. The two aromatic rings (C4–C9 and C17–C22) are inclined to one another by 8.39 (9)° and the molecule has an E conformation about the C2═C3 bond.

In the crystal, the molecules stack head-to-tail along the b axis. They molecules are linked by very weak C-H···O and C-H···π interactions (Table 1). Atom O1 of the carbonyl group interacts with the H atom, H2, of the C2═ C3 double bond in a C═O···HC═C fashion, resulting in the formation of C(4) chains along the a-axis direction. In addition, the O atom, O2, of the ether moiety is also involved in a weak hydrogen bond with the central phenyl group of an inversion related neighboring molecule. The two molecules are arranged head-to-tail, which induces formation of an inversion dimeric unit and an eight-membered R₂²(8) ring containing a pair of very weak C-H···O hydrogen bonds (Table 1).

As a result of the head-to-tail flipping, there is no ring alignment within the structure, hence the system lacks any significant π–π interactions but there are C—H···π contacts present (Table 1) which link the double stranded chains to form a two-dimensional network.

2. Experimental

The title compound was obtained by mixing acetophenone (0.150 g, 1.22 mmol), 4-(heptyloxy)benzaldehyde (0.269 g, 1.22 mmol), a 10% solution of NaOH and ethanol at 273 K for 18 h, after which it was acidified with 1 N HCl. The crude product obtained was recrystallized from ethanol yielding yellow plate-like crystals.