(1E,4E)-1,5-Bis(4-methyl­phen­yl)penta-1,4-dien-3-one

Muhammad Nadeem Arshad; Muhammad Nawaz Tahir; Muhammad Nadeem Asghar; Islam Ullah Khan; Muhammad Ashfaq

doi:10.1107/S1600536808020084

. 2008 Jul 5;64(Pt 8):o1413. doi: 10.1107/S1600536808020084

(1E,4E)-1,5-Bis(4-methylphenyl)penta-1,4-dien-3-one

Muhammad Nadeem Arshad ^a, Muhammad Nawaz Tahir ^b,^*, Muhammad Nadeem Asghar ^a, Islam Ullah Khan ^a, Muhammad Ashfaq ^a

PMCID: PMC2962047 PMID: 21203132

Abstract

The title compound, C₁₉H₁₈O, crystallizes in a non-centrosymmetric space group although the molecule has no chiral centre. The dihedral angle between the aromatic rings is 20.43 (13)°. The structure is stabilized by two intramolecular hydrogen bonds, and by four π–π and three C—H⋯π interactions between the aromatic rings. The perpendicular distances between the centroids of the rings involved in the π–π interactions have values of 1.996, 2.061, 2.181 and 2.189 Å.

Related literature

For related literature, see: Butcher et al. (2006 ▶); Conard & Dolliver (1943 ▶); Harrison et al. (2006 ▶).

Experimental

Crystal data

C₁₉H₁₈O
M _r = 262.33
Monoclinic,
a = 19.937 (2) Å
b = 5.8637 (5) Å
c = 14.9207 (14) Å
β = 121.001 (3)°
V = 1495.1 (2) Å³
Z = 4
Mo Kα radiation radiation
μ = 0.07 mm⁻¹
T = 296 (2) K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.980, T _max = 0.988
9611 measured reflections
2288 independent reflections
1800 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.137
S = 1.04
2288 reflections
183 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020084/bq2087sup1.cif

e-64-o1413-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020084/bq2087Isup2.hkl

e-64-o1413-Isup2.hkl^{(110.2KB, hkl)}

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

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

CgA and CgB are the centroids of the C4–C9 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1	0.93	2.49	2.817 (4)	101
C12—H12⋯O1	0.93	2.48	2.819 (3)	102
C5—H5⋯CgAⁱ	0.93	2.82	3.523 (3)	133
C9—H9⋯CgBⁱⁱ	0.93	2.89	3.604 (3)	134
C18—H18⋯CgBⁱⁱⁱ	0.93	2.95	3.621 (3)	131

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

Acknowledgments

MNA gratefully acknowledges the Higher Education Commision, Islamabad, Pakistan, for providing a scholarship under the Indigenous PhD Programme (PIN 042-120607-PS2-183).

supplementary crystallographic information

Comment

The chalcones are being synthesized since long for various applications. The title compound (I) differs from 1,5-Bis(4-methoxyphenyl)penta-1,4- dien-3-one (II) (Harrison et al., 2006) and 1,5-Bis(4-chlorophenyl)penta-1,4- dien-3-one (III) (Butcher et al., 2006) due the attachement of methyl group at para position instead of methoxy or chloro moieties. The authors have reported their nonlinear optical (NLO) activity as the compounds crystallize in non-centrosymmetric space groups. The title compound have a monoclinic crystal system and a non-centrosymmetric space group C2. Therefore, it is assumed that this compound will also have nonlinear optical activity.

We compare the bond distances and bond angles realised in (I) with the corresponding values observed in (II) and (III). The central portion of (I) shows double and single bonds originating from O1-atom and five-C-atom behave like a backbone. In (I), the bond distance O1==C1 is 1.211 (4) Å, greater than 1.170 (12) Å (III) but shorter than 1.230 (6) Å as in (II). The bond distances C1—C2 = 1.480 (3) Å, C2==C3 = 1.329 (3) Å, C3—C4 = 1.465 (3) Å are observed in (I), in (II) and (III) the corresponding values are [1.476 (4), 1.318 (5), 1.475 (4) Å] and [1.579 (10), 1.239 (7), 1.502 (7) Å], respectively. The range of bond angles for backbone C-atoms in (I) is 116.0 (2)°-127.8 (2)°, whereas in (II) and (III), the range is 123.8 (5)°- 126.4 (4)° and 103.1 (9)°-128.5 (4)°, respectively. The dihedral angle between the aromatic rings A (C4—C9) and B (C13—C18) is 20.27 (13)°, which is less than 56.92 (9)° and 53.4 (5) as reported in (II) and (III), respectively. The title compound is stabilized due to two intramolecular H-bonding (Fig 1) and three C—H···π interactions as given in Table 1. There exist also π–π-interactions between the aromatic rings. The perpendicular distance between the centroids CgA and CgB [(CgA···CgA^iv), symmetry code: iv = -x + 1/2, y - 1/2, -z], [(CgA···CgB^v), symmetry code: v = -x + 1, y + 1, -z + 1], [(CgB···CgAⁱⁱ), symmetry code: ii = -x + 1, y, -z + 1] and [(CgB···CgB^vi), symmetry code: vi = -x + 3/2, y - 1/2, -z + 1] have values of 1.996, 2.181, 2.061 and 2.189 Å, respectively.

Experimental

The title compound (I) was synthesized using the method of Conard & Dolliver, 1943. Sodium hydroxide (0.8 g, 0.0208 mmol) was dissolved in distilled water (10 ml) and ethanol (8 ml) in a round bottom flask. The solution was cooled to room temperature. Half of the mixture of p-tolualdehide (1 g, 0.00833 mmol) and acetone (0.24 g, 0.00417 mmol) added to the above solution and stirred at room temperature for 15 minute then the remaining mixture was added and stirred for 2 h under the same conditions. Yellow precipitate obtained was filtered and washed with cold water. The washed precipitate was crystallized in aceton under slow evaporation.