(2E)-3-(1,3-Diphenyl-1H-pyrazol-4-yl)-1-phenyl­prop-2-en-1-one

Hoong-Kun Fun; Madhukar Hemamalini; Shridhar Malladi; Pradeep Poojari; Arun M Isloor

doi:10.1107/S1600536811023282

. 2011 Jun 18;67(Pt 7):o1745–o1746. doi: 10.1107/S1600536811023282

(2E)-3-(1,3-Diphenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one

Hoong-Kun Fun ^a,^*,^‡, Madhukar Hemamalini ^a, Shridhar Malladi ^b, Pradeep Poojari ^b, Arun M Isloor ^b

PMCID: PMC3151840 PMID: 21837132

Abstract

In the title compound, C₂₄H₁₈N₂O, the pyrazole ring is essentially planar [maximum deviation = 0.004 (1) Å] and makes dihedral angles of 18.07 (4), 48.60 (4) and 9.13 (5)° with the phenyl rings. In the crystal, adjacent molecules are connected via intermolecular C—H⋯O hydrogen bonds, forming dimers. Furthermore, the crystal structure is stabilized by weak C—H⋯π and π–π interactions, with centroid–centroid distances of 3.6808 (5) Å.

Related literature

For applications of pyrazoles, see: Patel et al. (2004 ▶); Isloor et al. (2009 ▶); Vijesh et al. (2010 ▶); Sharma et al. (2010 ▶); Rostom et al. (2003 ▶); Ghorab et al. (2010 ▶); Amnekar & Bhusari (2010 ▶). For the synthetic procedure, see: Sharma et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₄H₁₈N₂O
M _r = 350.40
Triclinic,
a = 8.1027 (2) Å
b = 9.3157 (2) Å
c = 12.9634 (3) Å
α = 73.630 (1)°
β = 74.713 (1)°
γ = 74.820 (1)°
V = 886.83 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.66 × 0.23 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.949, T _max = 0.988
27273 measured reflections
7371 independent reflections
6190 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.131
S = 1.04
7371 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023282/rz2615sup1.cif

e-67-o1745-sup1.cif^{(21.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023282/rz2615Isup2.hkl

e-67-o1745-Isup2.hkl^{(360.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811023282/rz2615Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg2 and Cg3 are the centroids of the C20–C25 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1ⁱ	0.95	2.27	3.2019 (11)	167
C15—H15A⋯Cg2ⁱⁱ	0.95	2.81	3.6171 (9)	143
C2—H2A⋯Cg3ⁱⁱⁱ	0.95	2.63	3.4304 (9)	143

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

Acknowledgments

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks the Universiti Sains Malaysia for a post-doctoral research fellowship. AMI thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for a Young Scientist’s award.

supplementary crystallographic information

Comment

Pyrazoles are a novel class of heterocyclic compounds possessing wide variety of applications in the agrochemical and pharmaceutical industries (Patel et al., 2004). Derivatives of pyrazoles are found to show good antibacterial (Isloor et al., 2009; Vijesh et al., 2010), anti-inflammatory (Sharma et al., 2010), analgesic (Rostom et al., 2003), anticancer, radioprotective (Ghorab et al., 2010) and anti-convulsant activities (Amnekar et al., 2010). Prompted by these diverse activities of pyrazole derivatives, we have synthesized the title compound to study its crystal structure.

In the title compound (Fig. 1), the pyrazole (N1/N2/C10–C12) group is essentially planar, with a maximum deviation of 0.004 (1) Å for atom C12, and makes dihedral angles of 18.07 (4)°, 48.60 (4)° and 9.13 (5)° with the adjacent C1–C6, C13–C18) and C19–C24 phenyl rings, respectively.

In the crystal structure (Fig. 2), adjacent molecules are connected via intermolecular C12—H12A···O1 (Table 1) hydrogen bonds forming dimers. Furthermore, the crystal structure is stabilized by weak π–π interactions between the pyrazole (N1/N2/C10–C12) and phenyl (C19–C24) rings [Cg···Cg = 3.6808 (5) Å; -x, 2-y, 1-z] and C—H···π (Table 1) interactions, involving the centroids of the C20–C25 (Cg2) and C13–C18 (Cg3) rings.

Experimental

To a cold stirred mixture of methanol (20 ml) and sodium hydroxide (12.09 mmol) was added acetophenone (4.03 mmol). The reaction mixture was stirred for 10 min. To this solution was added formyl pyrazole (4.03 mmol) followed by tetrahydrofuran (30 ml). The solution was further stirred for 2 h at 0 °C and then at room temperature for 5 h. It was then poured into ice cold water. The resulting solution was neutralized with diluted HCl. The solid that separated out was filtered, washed with water, dried and crystallized from ethanol. Yield: 1.15 g, 81.5 %. M. p.: 406–408 K (Sharma et al., 2010).