(2E)-3-(4-Methyl­phen­yl)-1-(3-nitro­phen­yl)prop-2-en-1-one

Jerry P Jasinski; Ray J Butcher; B Narayana; K Lakshmana; H S Yathirajan

doi:10.1107/S160053680706182X

. 2007 Dec 6;64(Pt 1):o1–o2. doi: 10.1107/S160053680706182X

(2E)-3-(4-Methylphenyl)-1-(3-nitrophenyl)prop-2-en-1-one

Jerry P Jasinski ^a,^*, Ray J Butcher ^b, B Narayana ^c, K Lakshmana ^c, H S Yathirajan ^d

PMCID: PMC2914892 PMID: 21200665

Abstract

The title compound, C₁₆H₁₃NO₃, crystallizes with two independent molecules (A and B) in the asymmetric unit. The dihedral angle between the mean planes of the 4-methylphenyl and 3-nitrophenyl groups is 4.0 (3)° in molecule A and 16.2 (7)° in molecule B. Intermolecular C—H⋯O hydrogen bonding involving the O atoms of the 3-nitrophenyl group of both independent molecules link the molecules into layers approximately parallel to the (110) plane. The layers are held together by π–π stacking interactions between the 4-methylphenyl ring of molecule A and the 3-nitrophenyl ring of molecule B of the adjacent layer, with the distance between the centroids of interacting rings being 3.6987 (7) Å.

Related literature

For related structures, see: Butcher, Jasinski, Narayana et al. (2007 ▶); Butcher, Jasinski, Yathirajan, Narayana et al. (2007 ▶); Butcher, Jasinski, Yathirajan, Veena et al. (2007 ▶); Rosli et al. (2007 ▶); Patil et al. (2007 ▶). For related literature, see: Dimmock et al. (1999 ▶); Go et al. (2005 ▶); Goto et al. (1991 ▶); Uchida et al. (1998 ▶); Tam et al. (1989 ▶).

Experimental

Crystal data

C₁₆H₁₃NO₃
M _r = 267.27
Triclinic,
a = 8.0951 (3) Å
b = 11.5088 (5) Å
c = 14.6970 (5) Å
α = 80.351 (3)°
β = 74.830 (3)°
γ = 84.416 (3)°
V = 1300.78 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 (2) K
0.41 × 0.35 × 0.28 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.874, T _max = 0.974
19776 measured reflections
8636 independent reflections
4667 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.127
S = 0.97
8636 reflections
363 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: CrysAlisPro (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2000 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706182X/ci2518sup1.cif

e-64-000o1-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706182X/ci2518Isup2.hkl

e-64-000o1-Isup2.hkl^{(422.4KB, 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
C2A—H2A⋯O2B	0.93	2.55	3.4644 (16)	170
C11A—H11A⋯O2B	0.93	2.59	3.5156 (14)	176
C2B—H2B⋯O2Aⁱ	0.93	2.51	3.4311 (16)	171
C14A—H14A⋯O3Aⁱⁱ	0.93	2.54	3.4455 (16)	164

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

Acknowledgments

KL thanks Mangalore University for use of their research facilities. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

Chalcones can be easily obtained from the Claisen-Schmidt reaction of aromatic aldehydes and aromatic ketones. Chalcones have been reported to possess many useful properties including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumour and anticancer activities (Dimmock et al. 1999; Go et al. 2005). They are also important intermediates in organic synthesis. Among several organic compounds reported to have NLO properties, chalcone derivatives are recognized material because of their excellent blue light transmittance and good crystallization ability. They provide necessary configuration to show NLO properties having two planar rings connected through a conjugated double bond (Goto et al. 1991; Uchida et al. 1998; Tam et al. 1989). The crystal structures of 1-(3-hydroxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one (Butcher, Jasinski, Narayana et al., 2007), (2E)-1-(4-methylphenyl)-3-(4-nitrophenyl)prop-2-en-1-one (Butcher, Jasinski, Yathirajan, Veena et al., 2007), (E)-3-(4-fluorophenyl)-1-(4-methylphenyl)prop-2-en-1-one (Butcher, Jasinski, Yathirajan, Narayana et al. 2007), 3-(dimethylaminophenyl)-1-(3-nitrophenyl)prop-2-en-1-one (Rosli et al. 2007) and 3-(5-bromo-2-thienyl)-1-(4-nitrophenyl)prop-2-en-1-one (Patil et al. 2007) have been reported. We report here the crystal structure of a new chalcone, the title compound.

The title compound crystallizes with two independent molecules (A and B) in the asymmetric unit (Fig. 1). The dihedral angle between the mean planes of the 4-methylphenyl and 3-nitrophenyl groups is 4.0 (3)° in molecule A and 16.2 (7)° in molecule B. Crystal packing is stabilized by intermolecular C—H···O hydrogen bonding involving the O atoms on the 3-nitrophenyl group of both indpendent molecules. These hydrogen bonds (Table 1) link the molecules into a layer approximately parallel to the (1 1 0) plane (Fig. 2). Intermolecular π-π stacking interactions occur between 4-methylphenyl ring of molecule A at (x, y, z) and 3-nitrophenyl ring of molecule B of the adjacent layer at (1 - x, 1 - y, -z), with the distance between the centroids of interacting rings being 3.6987 (7) Å.

Experimental

A solution of 1-(3-nitrophenyl)ethanone (1.65 g, 0.01 mol) and 4-methylbenzaldehyde (1.20 g, 0.01 mol) in ethanol (25 ml) was stirred well and 10% NaOH solution (5 ml) was added. The reaction mixture was stirred for about 6 h and filtered. The product was crystallized from acetone (m.p. 414–416 K). Single crystals suitable for X-ray structure determination were grown by slow evaporation of an acetone solution of the title compound at room temperature. Analysis found: C 71.82, H 4.85, N 5.20%; C₁₆H₁₃NO₃ requires: C 71.90, H 4.90, N 5.24%.