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

T S Yamuna; H S Yathirajan; Jerry P Jasinski; Amanda C Keeley; B Narayana; B K Sarojini

doi:10.1107/S1600536813010854

. 2013 Apr 27;69(Pt 5):o790–o791. doi: 10.1107/S1600536813010854

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

T S Yamuna ^a, H S Yathirajan ^a, Jerry P Jasinski ^b,^*, Amanda C Keeley ^b, B Narayana ^c, B K Sarojini ^d

PMCID: PMC3648313 PMID: 23723933

Abstract

In the title compound, C₁₅H₁₀ClNO₃, a substituted chalcone, the dihedral angle between the benzene rings is 5.1 (7)°. The nitro group makes a dihedral angle of 12.5 (3)° with the benzene ring to which it is attached. In the crystal, weak C—H⋯O interactions link the molecules into a one-dimensional array along [010]. The crystal studied was an inversion twin, with a refined ratio for the twin components of 0.6060 (9):0.3939 (1).

Related literature

For the biochemical activity of chalcones, see: Dimmock et al. (1999 ▶). For different chalcone derivatives, see: Samshuddin et al. (2010 ▶); Fun et al. (2010a ▶,b ▶); Jasinski et al. (2010a ▶,b ▶); Baktır et al. (2011a ▶,b ▶). For related structures, see: Jing (2009 ▶); Jasinski et al. (2008 ▶, 2010a ▶,b ▶); Fun et al. (2011 ▶); Sarojini et al. (2007 ▶); Ma (2007 ▶). graphic file with name e-69-0o790-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₀ClNO₃
M _r = 287.69
Orthorhombic,
a = 42.9266 (17) Å
b = 5.9741 (3) Å
c = 5.0680 (2) Å
V = 1299.68 (10) Å³
Z = 4
Cu Kα radiation
μ = 2.67 mm⁻¹
T = 173 K
0.42 × 0.08 × 0.04 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T _min = 0.803, T _max = 1.000
12814 measured reflections
2538 independent reflections
2481 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.100
S = 1.14
2538 reflections
182 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Click here for additional data file.^{(580.4KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813010854/fj2627sup1.cif

e-69-0o790-sup1.cif^{(580.4KB, cif)}

Click here for additional data file.^{(139.5KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010854/fj2627Isup2.hkl

e-69-0o790-Isup2.hkl^{(139.5KB, hkl)}

Click here for additional data file.^{(4.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813010854/fj2627Isup3.cml

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
C12—H12⋯O2ⁱ	0.93	2.69	3.304 (4)	125
C14—H14⋯O1ⁱⁱ	0.93	2.53	3.219 (4)	131

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

Acknowledgments

TSY thanks the University of Mysore for research facilities. BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) 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). The basic skeleton of chalcones which possess α,β-unsaturated carbonyl group is useful synthone for the synthesis of various biodynamic cyclic derivatives such as pyrazoline, benzodiazepine and cyclohexenone derivatives (Samshuddin et al., 2010; Fun et al., 2010a,b; Jasinski et al., 2010a; Baktır et al., 2011a,b). The crystal structures of some of chalcones containing nitro group, viz., (E)-1-(4-nitrophenyl)-3-phenylprop-2-en-1-one (Jing, 2009), (2E)-3-(4-methylphenyl)-1-(3-nitrophenyl)prop-2-en-1-one (Jasinski et al., 2008), (2E)-3-(2-chlorophenyl)-1-(3-nitrophenyl)prop-2-en-1-one (Sarojini et al., 2007); (2E)-1-(2,5-dimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one (Fun et al., 2011) and (E)-3-(4-methoxyphenyl)-1-(3-nitrophenyl)prop-2-en-1-one (Ma, 2007) have been reported. In continuation of our work on synthesis of chalcones (Jasinski et al., 2010b) we report here in the crystal structure of the title compound C₁₅H₁₀ClNO₃, (I).

In (I), the dihedral angle between the mean planes of the 4-chlorophenyl and 4-nitrophenyl rings is 5.1 (7)° (Fig. 1). The nitro group makes a dihedral angle of 12.5 (3)° with the plane of the benzene to which it is bonded. In the crystal, weak C—H···N intermolecular interactions are observed and contribute to packing stability (Fig. 2). The crystal studied was an inversion twin, the refined ratio of the twin components being 0.6060 (9):0.3939 (1).

Experimental

To a mixture of 4-nitrobenzaldehyde (1.51 g, 0.01 mol) and 4-chloroacetophenone (1.54 g, 0.01 mol) in ethanol (50 ml), 10 ml of 10% sodium hydroxide solution was added and stirred at 278-283 K for 3 hours (Fig. 3). The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from acetone by the slow evaporation method (m.p.: 413–418 K).