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

Hoong-Kun Fun; Suchada Chantrapromma; P S Patil; S M Dharmaprakash

doi:10.1107/S160053680801218X

. 2008 May 3;64(Pt 6):o958–o959. doi: 10.1107/S160053680801218X

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

Hoong-Kun Fun ^a,^*, Suchada Chantrapromma ^b,^‡, P S Patil ^c, S M Dharmaprakash ^c

PMCID: PMC2961413 PMID: 21202689

Abstract

In the title compound, C₁₅H₁₀ClNO₃, a substituted chalcone, the 2-chlorophenyl and 4-nitrophenyl rings make a dihedral angle of 26.48 (6)°. The nitro group makes a dihedral angle of 11.64 (7)° with the plane of the benzene ring to which it is bound. Weak intramolecular C—H⋯O and C—H⋯Cl interactions involving the enone groups generate S(5) ring motifs, which help to stabilize the planarity of the 3-(2-chlorophenyl)prop-2-en-1-one segment of the molecule. In the crystal structure, adjacent molecules are stacked in a head-to-tail fashion into columns along the a axis by π–π interactions [centroid–centroid distance = 3.6955 (8) Å]. Neighbouring columns are linked by weak C—H⋯O interactions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see, for example: Fun et al. (2007 ▶); Patil et al. (2006b ▶; 2007a ▶,b ▶,c ▶). For background to the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999 ▶); Gu et al. (2008 ▶); Patil et al. (2006a ▶, 2007c ▶,d ▶).

Experimental

Crystal data

C₁₅H₁₀ClNO₃
M _r = 287.69
Monoclinic,
a = 13.7003 (2) Å
b = 7.3659 (1) Å
c = 25.9954 (4) Å
β = 102.290 (1)°
V = 2563.21 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 100.0 (1) K
0.36 × 0.22 × 0.14 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.899, T _max = 0.957
27534 measured reflections
3736 independent reflections
3008 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.103
S = 1.07
3736 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801218X/sj2489sup1.cif

e-64-0o958-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801218X/sj2489Isup2.hkl

e-64-0o958-Isup2.hkl^{(183.3KB, 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
C4—H4⋯O2ⁱ	0.93	2.58	3.4284 (18)	152
C5—H5⋯O1ⁱⁱ	0.93	2.59	3.2996 (17)	134
C7—H7⋯Cl1	0.93	2.60	3.0531 (14)	110
C7—H7⋯O1	0.93	2.47	2.7981 (16)	101
C12—H12⋯O1ⁱⁱⁱ	0.93	2.56	3.3298 (17)	141

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

Acknowledgments

PSP thanks the DRDO, Government of India, for a Senior Research Fellowship (SRF). This work is supported by the Department of Science and Technology (DST), Government of India, under grant No. SR/S2/LOP-17/2006. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Chalcone derivatives have been extensively studied in attempts to obtain non-linear optical (NLO) materials (Agrinskaya et al., 1999; Patil et al., 2006a, 2007c, 2007d). We have previously synthesized and crystallized several chalcone derivatives to study their non-linear optical properties (Agrinskaya et al., 1999; Fun et al., 2007; Patil et al., 2006a, 2007a, 2007b, 2007c, 2007d). As part of our studies on structure-property relationships of chalcones and the importance of substituted chalcones in nonlinear optics (Agrinskaya et al., 1999; Patil et al., 2006a, 2007c, 2007d), the title compound was synthesized and its crystal structure is reported here. Unfortunately this crystal does not have second-order NLO properties because it crystallizes in the centrosymmetric C2/c space group.

The molecular structure of the title compound (Fig. 1) is not planar as indicated by the dihedral angle between the 4-nitrobenzene and 2-chlorobenzene rings being 26.48 (6)°. The propene unit (C7/C8/C9) is co-planar with the 2-chlorobenzene ring with the torsion angle C6–C7–C8–C9 = -178.41 (12)°. Atoms O1, C8, C9 and C10 lie on a plane and the least-squares plane through this moiety makes dihedral angles of 8.69 (7)° and 26.48 (6)° with the 4-nitrobenzene and 2-chlorolbenzene rings, repectively. The nitro group makes a dihedral angle of 11.64 (7)° with the plane of the benzene ring to which it is bound. Bond lengths and angles shown normal values (Allen et al., 1987) and are comparable to those in related structures (Fun et al., 2007; Patil et al., 2006b; 2007a; 2007b; 2007c; 2007d). In the structure of the title compound, weak intramolecular C7—H7···O1 and C7—H7···Cl1 interactions generate S(5) ring motifs (Bernstein et al., 1995) (Fig. 1 and Table 1) which help to stabilize the planarity of the (2-chlorophenyl)prop-2-en-1-one segment of the molecule.

In the crystal structure (Fig. 2), adjacent molecules are stacked in a head to tail fashion into columns along the a-axis by π···π interactions with the distances of Cg₁···Cg₂ = 3.6955 (8) Å: symmetry code 1/2 - x, 1/2 + y, 1/2 - zCg₁ and Cg₂ are the centroids of C1–C6 and C10–C15, respectively. The neighbouring columns are linked by weak C—H···O interactions (Table 1).

Experimental

The title compound was synthesized by the condensation of 2-chlorobenzaldehyde (0.01 mol) with 4-nitroacetophenone (0.01 mol) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring for 4 hr, the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 5 hr. The resulting crude solid was filtered and dried. Colorless single crystals of the title compound suitable for x-ray structure determination were recrystallized from N,N-dimethylformamide (DMF).