5-(4-Chloro­phen­oxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde

N Vinutha; S Madan Kumar; S Shobhitha; B Kalluraya; N K Lokanath; D Revannasiddaiah

doi:10.1107/S1600536814007879

. 2014 Apr 16;70(Pt 5):o560. doi: 10.1107/S1600536814007879

5-(4-Chlorophenoxy)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde

N Vinutha ^a, S Madan Kumar ^a, S Shobhitha ^b, B Kalluraya ^b, N K Lokanath ^a, D Revannasiddaiah ^a,^*

PMCID: PMC4011310 PMID: 24860367

Abstract

In the title compound, C₁₇H₁₃ClN₂O₂, the phenyl and chlorobenzene rings are inclined to the central pyrazole ring at 40.84 (9) and 65.30 (9)°, respectively. In the crystal, pairs of C—H⋯π interactions link the molecules into inversion dimers and C—H⋯O hydrogen bonds link these dimers into columns extended in [010]. The crystal packing exhibits short intermolecular O⋯Cl contacts of 3.0913 (16) Å.

Related literature

For biological properties and pharmocological applications of aryloxy pyrazole derivatives, see: Rai et al. (2008 ▶); Girisha et al. (2010 ▶); Isloor et al. (2009 ▶, 2010 ▶); Shobhitha et al. (2013 ▶). For related structures, see: Shahani, Fun, Ragavan et al. (2011 ▶); Shahani, Fun, Shetty et al. (2011 ▶); Prasath et al. (2011 ▶).

Experimental

Crystal data

C₁₇H₁₃ClN₂O₂
M _r = 312.74
Monoclinic,
a = 9.1016 (7) Å
b = 7.5298 (6) Å
c = 22.1242 (16) Å
β = 93.908 (3)°
V = 1512.7 (2) Å³
Z = 4
Cu Kα radiation
μ = 2.31 mm⁻¹
T = 296 K
0.23 × 0.22 × 0.21 mm

Data collection

Bruker X8 Proteum diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T _min = 0.619, T _max = 0.643
9744 measured reflections
2501 independent reflections
2314 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.105
S = 1.03
2501 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814007879/cv5447sup1.cif

e-70-0o560-sup1.cif^{(24.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007879/cv5447Isup2.hkl

e-70-0o560-Isup2.hkl^{(120.4KB, hkl)}

Click here for additional data file.^{(5.6KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814007879/cv5447Isup3.cml

CCDC reference: 996262

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.93	2.58	3.503 (2)	171
C2—H2⋯Cg ⁱⁱ	0.93	2.63	3.476 (2)	152

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

Acknowledgments

The authors are thankful to the IOE and UPE, University of Mysore, for providing the single-crystal X-ray diffraction facility and for the financial support. VN is grateful to the UGC for the award of an RFSMS Fellowship. RD acknowledges the UGC, New Delhi, for financial support under the Major Research Project Scheme [UGC MRP No. F.41–882/2012 (SR) dated 01/07/2012].

supplementary crystallographic information

1. Comment

Aryloxy pyrazoles and their derivatives possess a significant pharmcological activities such as antimicrobial (Rai et al. 2008; Girisha et al., 2010), anti-inflammatory (Isloor et al., 2009) and analgesic activities (Shobhitha et al., 2013). The title compound can serve as an intermediate in the synthesis of various pyrazole derivatives with significant pharmacological activities (Isloor et al., 2010).

In the title compound (Fig.1), all bond lengths and angles are normal and correspond well to those observed in the related compounds (Shahani, Fun, Ragavan et al., 2011; Shahani, Fun, Shetty et al., 2011; Prasath et al., 2011). The pyrazole ring makes dihedral angles of 65.30 (9)° with chlorobenzene ring and 40.84 (9)° with benzene ring. The dihedral angle between the chlorobenzene ring and benzene ring is 76.23 (9)°.

In the crystal, C–H···π interactions (Table 1) link the molecules into inversion dimers, and intermolecular C–H···O hydrogen bonds (Table 1) link these dimers into columns extended in [010]. The crystal packing exhibits short intermolecular O···Cl contacts of 3.0913 (16) Å.

2. Experimental

The title compound was prepared by refluxing a mixture of 5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-carboxaldehyde (0.1 mol) and 4-chloro phenol (0.1 mol) in 10 ml of dimethyl sulfoxide. To this solution, 0.1 mol of potassium hydroxide was added. The reaction mixture was refluxed for 3 hrs and then it 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 slow evaporation of ethanol.