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

Grzegorz Dutkiewicz; S Samshuddin; B Narayana; H S Yathirajan; Maciej Kubicki

doi:10.1107/S1600536809050508

. 2009 Nov 28;65(Pt 12):o3255–o3256. doi: 10.1107/S1600536809050508

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

Grzegorz Dutkiewicz ^a, S Samshuddin ^b, B Narayana ^b, H S Yathirajan ^c, Maciej Kubicki ^a,^*

PMCID: PMC2971946 PMID: 21578952

Abstract

In the title compound, C₁₉H₁₃ClO, the benzene ring and the naphthalene system, are twisted by 12.3 (3) and 36.1 (2)°, respectively, and in opposite directions with respect to the central propenone bridge. The bond-angle pattern within the benzene ring is influence by both substituents; these influences are almost additive. In the crystal, the molecules are linked by C—H⋯O and C—H⋯Cl interactions.

Related literature

For chalcones, see: Dhar (1981 ▶); Di Carlo et al. (1999 ▶); Dimmock et al. (1999 ▶); Goto et al. (1991 ▶); Indira et al. (2002 ▶); Sarojini et al. (2006 ▶); Satyanarayana et al. (2004 ▶); Uchida et al. (1998 ▶); Yarishkin (2008 ▶). For the 1-naphtyl analogue, see: Eswaramoorthy et al. (1994 ▶). For the influence of substituents on the geometry of the phenyl ring, see: Domenicano (1988 ▶). For a description of the Cambridge Crystallographic Database, see: Allen (2002 ▶). graphic file with name e-65-o3255-scheme1.jpg

Experimental

Crystal data

C₁₉H₁₃ClO
M _r = 292.74
Monoclinic,
a = 12.0392 (14) Å
b = 8.0544 (5) Å
c = 7.8472 (6) Å
β = 98.091 (10)°
V = 753.36 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 295 K
0.30 × 0.20 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire2, large Be window) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.666, T _max = 1.000
2481 measured reflections
1866 independent reflections
1440 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.083
S = 0.96
1866 reflections
190 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.13 e Å⁻³
Absolute structure: Flack (1983 ▶), 423 Friedel pairs
Flack parameter: 0.08 (7)

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050508/fk2008sup1.cif

e-65-o3255-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050508/fk2008Isup2.hkl

e-65-o3255-Isup2.hkl^{(89.9KB, 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
C17—H17⋯O12ⁱ	0.93	2.42	3.180 (4)	139
C3—H3⋯Cl21ⁱⁱ	0.93	2.92	3.703 (3)	143
C8—H8⋯O12ⁱⁱⁱ	0.93	2.64	3.546 (4)	163

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

Acknowledgments

SS thanks Mangalore University for the research facilitie.

supplementary crystallographic information

Comment

Chalcones constitute an important family of flavonoids. They have been reported to possess many interesting pharmacological activities (Dhar, 1981) including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Dimmock et al., 1999; Satyanarayana et al., 2004). Some chalcones demonstrated the ability to block voltage-dependent potassium channels (Yarishkin et al., 2008). Chalcones are also finding application as organic nonlinear optical materials (NLO) for their SHG conversion efficiency (Sarojini et al., 2006). Chalcone derivatives are recognized material in the NLO applications because of their excellent blue light transmittance and good crystallization ability (Goto et al.,1991; Uchida et al.,1998; Indira et al., 2002). Chemically chalcones consists of open-chain flavonoids in which the two aromatic rings are joined by α,\&s-unsaturated carbonyl system. The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using these compounds or chalcone rich plant extracts as drugs or food preservatives (Di Carlo et al., 1999). As a part of our efforts on the synthesis of naphthyl chalcones, this paper describes the crystal structure of a new naphthyl chalcone, (2E)-3-(4-Chlorophenyl)-1-(naphthalen-1-yl)prop-2-en-1-one (I, Scheme 1). There are 298 structures in the Cambridge Crystallographic Database (Allen, 2002: Ver. 5.30, Nov. 2008, last update Sep. 2009) that posses two aromatic moieties connected via CH=CH—CO– fragment, but only 10 of them are naphthyl chalcones, and the single one example with 1-naphthalene substituent (1-(1-Naphthalenyl)-3-(4-nitrophenyl)-2-propenone, Eswaramoorthy et al., 1994). It might be noted, that this structure apparently has errors: one of the torsion angles in the aromatic ring is as large as 5°.

The molecule of I is built of three approximately planar fragments (Fig. 1): the phenyl ring (A, maximum deviation form the least-squares plane is 0.006 (3) Å), propenone fragment C=C—C=O (B, 0.014 (2) Å), and the naphtalene ring system (C). This last fragment however is significantly folded, even though both individual rings are almost planar, the dihedral angle between these planes is as high as 5.05 (13)°. The overall conformation of I can be described in terms of dihedral angles between these fragments: A/B 36.1 (2)°, B/C 12.3 (3)°, and A/C 25.51 (9)°. These values show that the terminal planes are twisted in opposite sense with respect to the central bridging fragment. This situation is relatively rare, the majority of chalcones found in the CDB shows the same sense of rotation with respect to the central bridge.

The bond lengths within the conjugated linear fragment suggest the large degree of localization: C—C bond length of 1.480 (4) Å, C=C of 1.329 (4)Å and C=O 1.232 (3) Å. The bond angles within the phenyl ring are influenced by both Cl and C=C– substituents, and these influences are almost additive, as suggested e.g., by Domenicano (1988). The distribution is almost symmetrical with respect to the C15···C18 line, and the values are close to those calculated by summing the effects of both substituents.

In the crystal structure there is one relatively short C—H···O potential hydrogen bond, C17—H17···O12(x,1 + y,z), that link molecules into infinite chains along y direction, and few weak C—H···O and C—H···π contacts, which can stabilize the packing otherwise determined by the van der Waals interactions and close packing requirements (Fig. 2).

Experimental

To a mixture of 1-acetonaphthone (1.7 g, 0.01 mol) and p-chlorobenzaldehyde (1.4 g, 0.01 mol) in 30 ml e thanol, 10 ml of 10% sodium hydroxide solution was added and stirred at 5–10 ^oC for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. The single-crystal was grown from DMF by slow evaporation method and yield of the compound was 82%. (m.p. 360–362 K). Analytical data: Found (Calculated): C %: 76.89 (77.95); H %: 4.23 (4.48).