Crystal structure of 1-(4-chlorophenyl)-3-{4-[2-(5-ethyl-pyridin-2-yl)- ethoxy]-phenyl}-propenone

Article abstract of DOI:10.1134/S0022476613030293

The title compound C₂₄H₂₂ClNO₂ belongs to the orthorhombic system, space group Pca2₁ with a = 12.1771(10) A, b = 4.9305(4) A, c = 34.419(3) A, α = β = γ = 90, V = 2066.5(3) A³, Z = 4, D_c =

Full text of DOI:10.1134/S0022476613030293

Journal of Structural Chemistry. Vol. 54, No. 3, pp. 645-647, 2013
Original Russian Text Copyright © 2013 by M. Kayalvizhi, G. Vasuki, K. Ramamurthi, Navin B Patel, Hemant R Patel
CRYSTAL STRUCTURE OF 1-(4-CHLOROPHENYL)-3-
{4-[2-(5-ETHYL-PYRIDIN-2-YL)-ETHOXY]-PHENYL}-PROPENONE
1
M. Kayalvizhi, G. Vasuki, K. Ramamurthi,
1
2
UDC 548.737
3
Navin B Patel, and Hemant R Patel
3
The title compound C24H22ClNO2 belongs to the orthorhombic system, space group Pca21 with a =
3
12.1771(10) Å, b = 4.9305(4) Å, c = 34.419(3) Å, α = β = γ = 90°, V = 2066.5(3) Å , Z = 4, Dc =
3
1.260 g/cm , F(000) = 824, R = 0.0402 and wR = 0.1144, S = 1.034, T = 293 K. The compound is a
chalcone with 4-chlorophenyl and [(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl substituents bonded at the
opposite ends of a propenone group, the biologically active region. The propenone bridge makes dihedral
angles of 10.61(23)° and 62.75(22)° respectively, with 4-chlorophenyl and the [(5-ethyl-pyridin-2-yl)-
ethoxy]-phenyl group.
DOI: 10.1134/S0022476613030293
Keywords: chalcones, propenone, chlorophenyl, pyridine ring.
Introduction. Chalcones or 1,3-diaryl-2-propen-1-ones belong to the flavonoid family. Chemically, they consist of
open-chain flavonoids in which two aromatic rings are joined by a three-carbon α-β-unsaturated carbonyl system. The rising
prevalence of multi-drug resistant gram-positive and gram-negative bacteria continues to provide impetus for the search for
and discovery of novel antimicrobial agents active against these pathogens [1]. A vast number of naturally occurring
chalcones are polyhydroxylated in the aryl rings. The radical quenching properties of the phenolic groups present in many
chalcones have raised interest in using the compounds or chalcone-rich plant extracts as drugs or food preservatives. Among
many useful properties that chalcones have been reported to possess include anti-inflammatory, antimicrobial, antifungal,
antioxidant, cytotoxic, HIV-1 protease inhibitory, tyrosinase inhibitory, antiprotozoal, antiulcer as well as other activities.
More importantly, chalcones have shown several anticancer activities as inhibitors of cancer cell proliferation, carcinogenesis
and metastasis [2-6]. Many chalcones have been assessed for their high antimalarial activity, which is probably a result of
Michael addition of nucleophilic species to the double bond of the enone [2]. Some chalcones demonstrated the ability to
block voltage-dependent potassium channels. Chalcones are also finding application as organic compounds reported to have
NLO properties; chalcone derivatives are a recognized material because of their excellent blue light transmittance and good
crystallization ability. The basic skeleton of chalcones is useful as the starting material for the synthesis of various
biodynamic heterocyclic compounds such as cyclohexane derivatives and pyrazoline derivatives [7]. Owing to the
importance of these flavonoid analogs, we report here the crystal structure of the title chalcone derivative.
1
2
Department of Physics, Kunthavai Naachiar Government Arts College (w) Autonomous, Tamilnadu, India. Crystal
Growth and Thin Film Laboratory, School of Physics, Bharathidasan University, Tamilnadu, India; vasuki.arasi@yahoo.com.
3
Department of Chemistry, Veer Narmad South Gujarat University, Gujarat, India. The text was submitted by the authors in
English. Zhurnal Strukturnoi Khimii, Vol. 54, No. 3, pp. 590-592, May-June, 2013. Original article submitted January 21,
2012.
0022-4766/13/5403-0645 © 2013 Springer Science+Business Media, Inc.
645

Fig. 1. The molecular structure of 1 with the atom numbering scheme.
Displacement ellipsoids are drawn at the 50% probability level.
Experimental. To a solution of 4-(2-(5-ethylpyridin-2-yl)ethoxy)benzaldehyde (0.01 mol) in methanol (50 ml),
4-chloro acetophenone (0.01 mol) was added in the presence of 2% NaOH solution (5 ml). The reaction mixture was stirred
for 10-12 h at room temperature. The solvent was distilled off and the crude product was poured into ice water. The
compound thus obtained was washed with water and recrystallised from ethanol. The compound was synthesized using the
published method [1, 4, 5, 8, 9]. A chemical diagram of compound 1 is shown in Scheme. CIF file containing complete
information on the studied structure
was deposited with CCDC, deposition number 854383, and is freely available upon
request from the following web site: www.ccdc.cam.ac.uk/data_request/cif.
X-ray crystallography. A brown crystal of title compound 1 with dimensions 0.35×0.30×0.25 mm was chosen for
the data collection. The data were collected with graphite-monochromated MoK radiation (λ = 0.71073 Å). For compound 1
α
data collection: APEX2 [10 ]; cell refinement: APEX2/SAINT [10]; data reduction: SAINT/XPREP [10]; molecular graphics:
ORTEP-3 [11] and Mercury [12] for Windows; publication software: PLATON [13]. The structure of compound 1 was
solved by direct methods using SHELXS-97 [14] and refined using SHELXL-97 [14]. All non-hydrogen atoms were assigned
anisotropic displacement parameters in the refinement. All hydrogen atoms were positioned geometrically and treated as
riding on their parent atoms, with C–H = 0.93 Å (aromatic) and 0.97 Å (methylene), and refined using a riding model with
Uiso(H) = 1.2Ueq or 1.5Ueq (parent atom). In the range 2.37-23.89, a total of 3210 reflections were collected, out of which
3 3
2693 were independent (Rint = 0.020). The maximum and minimum peaks and holes are 0.30 e/Å and –0.18 e/Å respectively.
S = 1.034 and wR = 0.1144.
Results and discussion. The title compound C24H22ClNO2 crystallized in the orthorhombic system, space group
3 3
Pca21 with a = 12.1771(10) Å, b = 4.9305(4) Å, c = 34.419(3) Å, α = β = γ = 90°, V = 2066.5(3) Å , Z = 4, D 1.260 g/cm ,
=
c
F(000) = 824, R = 0.0402 and wR = 0.1144, S = 1.034, T = 293 K. The compound is a chalcone with 4-chlorophenyl and [(5-
ethyl-pyridin-2-yl)-ethoxy]-phenyl substituents bonded at the opposite ends of a propenone group, the biologically active
region. The propenone unit (C16–C18/O2) is planar [r.m.s. derivation 0.0052 Å] and torsion angle C16–C17–O2 being
–1.67(61)°. The propenone bridge makes dihedral angles of 10.61(23)° and 62.75(22)° respectively with 4-chlorophenyl and
the [(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl group. The pyridine ring system and the benzene ring are oriented at a dihedral
angle of 83.42(10)°. The ethoxy group is coplanar with the phenyl ring [dihedral angle = 7.68(27)°]. Bond lengths [15] and
angles are within the normal range and are comparable to those of the closely related structures [2, 3, 6, 7, 16]. The widening
of the exocyclic angles C17–C16–C13 [128.4(3)°] and C16–C13–C12 [123.1(3)°] deviates significantly from the normal
646

value of 120° and might be due to the repulsion between H12 and H17 at C17 (H12…H17 = 2.2403 Å). The ethyl group is
equatorially substituted to the pyridine ring. While no classical hydrogen bonds are present, weak intermolecular C–H…π-
ring interactions are observed, which contribute to the stability of crystal packing. In the crystal, the molecules are stacked in
columns along the c axis and several intermolecular π–π interactions are present between the six-membered rings, with the
shortest distance of 3.573 Å, as observed in [17].
G. Vasuki thanks the Sophisticated Analytical Instrument Facility, IIT Madras, Chennai, for the X-ray data collection.
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