(2E)-1-(2-Hy­droxy-5-methyl­phen­yl)-3-(4-meth­oxy­phen­yl)prop-2-en-1-one

Hoong-Kun Fun; Suhana Arshad; B K Sarojini; V Musthafa Khaleel; B Narayana

doi:10.1107/S1600536811015054

. 2011 Apr 29;67(Pt 5):o1248–o1249. doi: 10.1107/S1600536811015054

(2E)-1-(2-Hydroxy-5-methylphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one

Hoong-Kun Fun ^a,^*,^‡, Suhana Arshad ^a, B K Sarojini ^b, V Musthafa Khaleel ^b, B Narayana ^c

PMCID: PMC3089145 PMID: 21754540

Abstract

In the title compound, C₁₇H₁₆O₃, the dihedral angle between the aromatic rings is 4.59 (7)° and an intramolecular O—H⋯O hydrogen bond generates an S(6) ring. In the crystal, adjacent molecules are linked by C—H⋯O hydrogen bonds, leading to the formation of [001] supramolecular chains. Weak C—H⋯π interactions consolidate the packing.

Related literature

For a related structure and background references to chalcones, see: Fun et al. (2010 ▶). For related structures, see: Chantrapromma et al. (2009 ▶, 2010 ▶); Fun et al. (2009 ▶); Horkaew et al. (2010 ▶); Lu et al. (2009 ▶); Suwunwong et al. (2009 ▶); Wang et al. (2009 ▶, 2010 ▶); Jasinski et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₇H₁₆O₃
M _r = 268.30
Monoclinic,
a = 12.6990 (18) Å
b = 8.8022 (13) Å
c = 13.172 (2) Å
β = 105.565 (2)°
V = 1418.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.46 × 0.32 × 0.18 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.962, T _max = 0.984
11493 measured reflections
4090 independent reflections
2608 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.131
S = 1.02
4090 reflections
187 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536811015054/hb5847sup1.cif

e-67-o1248-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015054/hb5847Isup2.hkl

e-67-o1248-Isup2.hkl^{(200.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811015054/hb5847Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.95 (2)	1.65 (2)	2.5112 (18)	149.4 (19)
C11—H11A⋯O3ⁱ	0.93	2.60	3.4317 (17)	149
C16—H16C⋯Cg1ⁱⁱ	0.96	2.81	3.5800 (18)	138

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

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). SA thanks the Malaysian Government and USM for the award of a research scholarship. VMK also thanks P. A. College of Engineering for research facilities.

supplementary crystallographic information

Comment

In continuation of our studies on the crystal structures of chalcones (Fun et al., 2010), we now report the synthesis and crystal structure of the title compound, (I). The structures of some related chalcones viz: (Z)-3-(9-anthryl)-1-(4-methoxyphenyl)prop-2-en-1-one (Chantrapromma et al., 2009), (Z)-3-(9-anthryl)- 1-(2-thienyl)prop-2-en-1-one (Fun et al., 2009), (E)-3- (anthracen-9-yl)-1-(4-bromophenyl)prop-2-en-1-one (Suwunwong et al., 2009), (Z)-3-(9-anthryl)-1-(4-bromophenyl)-2-(4-nitro-1H- imidazol-1-yl)prop-2-en-1-one (Lu et al., 2009),(Z)-3- (9-anthryl)-2-(4-nitro-1H-imidazol-1-yl)-1-p-tolylprop- 2-en-1-one (Wang et al., 2009), (E)-3-(9-anthryl)-1- (4-fluorophenyl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one (Wang et al., 2010), (E)-3-(anthracen-9-yl)-1-(furan-2-yl) prop-2-en-1-one (Horkaew et al., 2010), and an orthorhombic polymorph of (Z)-3-(9-anthryl)-1-(2-thienyl)prop-2-en-1-one (Chantrapromma et al., 2010) and 2(E)-3-(4-hydroxyphenyl)-1-(4-chlorophenyl) prop-2-en-1-one (Jasinski et al.,2011) have been reported.

The molecular structure is shown in Fig. 1. An intramolecular O1—H1O1···O2 hydrogen bond (Table 1) stabilizes the molecular structure and forms an S(6) ring motif (Bernstein et al., 1995). The dihedral angle between the phenyl (C1–C6) ring and the methoxy-substituted phenyl (C10–C15) ring is 4.59 (7)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structures (Fun et al., 2010).

In the crystal packing (Fig. 2), the molecules are linked into infinite one-dimensional chain along the c-axis by intermolecular C11—H11A···O3 hydrogen bonds (Table 1). There are also C—H···π interactions (Table 1) which involves C16 and phenyl ring (Cg1 = C1–C6).

Experimental

2-Hydroxy-5-methylacetophenone (1.50 g, 0.01 mol) was mixed with 4-methoxybenzaldehyde (1.36 g, 0.01 mol) and dissolved in ethanol (40 ml). To this solution, 5 ml of KOH (50%) was added at 278 K. The reaction mixture stirred for 6 h and poured on to crushed ice. The pH of this mixture was adjusted to 3–4 with 2 M HCl aqueous solution. The resulting crude yellow solid was filtered, washed successively with dilute HCl solution and distilled water and finally recrystallized from ethanol (95%) to give the pure chalcone. Orange blocks of (I) were grown by the slow evaporation of the solution of the compound in ethyl alcohol (m. p.: 361 K). Composition: Found (Calculated) for C₁₇H₁₆O₃, C: 76.10 (76.16); H: 6.01 (6.05).