3-Methyl-5-phen­oxy-1-phenyl-1H-pyrazole-4-carbaldehyde

Tara Shahani; Hoong-Kun Fun; Shobhitha Shetty; Balakrishna Kalluraya

doi:10.1107/S1600536811036786

. 2011 Sep 14;67(Pt 10):o2646. doi: 10.1107/S1600536811036786

3-Methyl-5-phenoxy-1-phenyl-1H-pyrazole-4-carbaldehyde

Tara Shahani ^a, Hoong-Kun Fun ^a,^*,^‡, Shobhitha Shetty ^b, Balakrishna Kalluraya ^b

PMCID: PMC3201428 PMID: 22064771

Abstract

In the title compound, C₁₇H₁₄N₂O₂, the pyrazole ring makes dihedral angles of 73.67 (4) and 45.99 (4)°, respectively, with the adjacent phenyl and phenoxy rings. In the crystal, there are no classical hydrogen bonds, but a weak C—H⋯π interaction is observed.

Related literature

For biological applications of pyrazole derivatives, see: Rai et al. (2008 ▶); Isloor et al. (2009 ▶); Girisha et al. (2010 ▶). For a related structure, see: Shahani et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₇H₁₄N₂O₂
M _r = 278.30
Monoclinic,
a = 8.6207 (1) Å
b = 7.1695 (1) Å
c = 22.9228 (3) Å
β = 99.168 (1)°
V = 1398.67 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.46 × 0.20 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.961, T _max = 0.988
24894 measured reflections
6610 independent reflections
5063 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.127
S = 1.06
6610 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.25 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/S1600536811036786/is2775sup1.cif

e-67-o2646-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036786/is2775Isup2.hkl

e-67-o2646-Isup2.hkl^{(323.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811036786/is2775Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯Cg1ⁱ	0.95	2.62	3.5052 (8)	156

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Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSH also thanks USM for the award of a research fellowship.

supplementary crystallographic information

Comment

Pyrazoles are a novel class of heterocyclic compounds possessing wide variety of application in the agrochemical and pharmaceutical industries. Derivatives of pyrazoles are found to show good antibacterial (Rai et al., 2008), anti-inflammatory and analgesic (Isloor et al., 2009) activities. In view of these observations and in continuation of our search for biologically active pyrazole derivatives, we herein report the crystal structure of 3-methyl-5-phenoxy-1-phenyl-1H-pyrazole-4-carbaldehyde. Reaction of 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde with phenol afforded 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (Girisha et al., 2010).

The asymmetric unit of the title compound is shown in Fig. 1. The 1H-pyrazole (N1/N2/C7–C9) ring is essentially planar with a maximum deviation of 0.004 (1) Å for atom N1. The central pyrazole ring makes dihedral angles of 73.67 (4) and 45.99 (4)° with the terminal phenyl (C1–C6) and (C10–C15) rings, respectively. The bond lengths (Allen et al., 1987) and angles are within normal ranges and is comparable to a closely related structure (Shahani et al., 2011).

In the crystal packing (Fig. 2), there are no classical hydrogen bonds but stabilization is provided by weak C—H···π (Table 1) interactions, involving the centroid Cg1 of the C1–C6 ring.

Experimental

5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-carboxaldehyde (0.1 mol) and phenol (0.1 mol) was dissolved in 10 mL of dimethyl sulfoxide. To this solution, 5.6 g (0.1 mol) of potassium hydroxide was added. The reaction mixture was refluxed for 6 hrs and then was cooled to room temperature and poured to crushed ice. The solid product that separated was filtered and dried. It was then recrystallized from ethanol. Crystals suitable for X-ray analysis were obtained from 1:2 mixtures of DMF and ethanol by slow evaporation.