1,3-Dimethyl-5-(3-methyl­phen­oxy)-1H-pyrazole-4-carbaldehyde

Hong Dai; Hai-Jun Zhang; Lei Shi; Hai-Qin Sun; Yu-Jun Shi

doi:10.1107/S1600536811050926

. 2011 Nov 30;67(Pt 12):o3510. doi: 10.1107/S1600536811050926

1,3-Dimethyl-5-(3-methylphenoxy)-1H-pyrazole-4-carbaldehyde

Hong Dai ^a, Hai-Jun Zhang ^a, Lei Shi ^a, Hai-Qin Sun ^a, Yu-Jun Shi ^a,^*

PMCID: PMC3239131 PMID: 22199979

Abstract

There are two independent molecules in the asymmetric unit of the title compound, C₁₃H₁₄N₂O₂, in which the dihedral angles between the substituted phenyl ring and the pyrazole ring are 86.5 (2) and 82.3 (3)°. The crystal packing features weak intermolecular C—H⋯O interactions.

Related literature

For the biological activity of pyrazole derivatives, see: Drabek (1992 ▶); Haga et al. (1990 ▶); Motoba et al. (1992 ▶); Watanabe et al. (2001 ▶).

Experimental

Crystal data

C₁₃H₁₄N₂O₂
M _r = 230.26
Triclinic,
a = 7.9444 (16) Å
b = 10.643 (3) Å
c = 15.053 (3) Å
α = 107.732 (3)°
β = 102.473 (5)°
γ = 93.225 (7)°
V = 1173.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 113 K
0.20 × 0.16 × 0.12 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T _min = 0.982, T _max = 0.989
12386 measured reflections
5529 independent reflections
2226 reflections with I > 2σ(I)
R _int = 0.064

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.100
S = 1.02
5529 reflections
313 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050926/ds2155sup1.cif

e-67-o3510-sup1.cif^{(23.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050926/ds2155Isup2.hkl

e-67-o3510-Isup2.hkl^{(270.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811050926/ds2155Isup3.cml

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
C12—H12A⋯O4ⁱ	0.98	2.57	3.488 (3)	157
C15—H15⋯O2ⁱⁱ	0.95	2.58	3.315 (3)	134

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (NNSFC) (grant No. 20772068), the Science and Technology Projects Fund of Nantong City (grant Nos. K2010016, AS2010005), the Science Foundation of Nantong University (grant Nos. 09Z010, 09 C001) and the Scientific Research Foundation for Talent Introduction of Nantong University.

supplementary crystallographic information

Comment

It is well known that compounds containing pyrazole ring have good bioactivities such as fungicidal, insecticidal, and herbicidal activities (Haga et al., 1990; Motoba et al., 1992; Watanabe et al., 2001). They are widely applied in the field of plant protection (Drabek, 1992). In order to discover more biologically active pyrazole compounds, the title compound, (I), was synthesized and its crystal structure was determined (Fig.1). The dihedral angles between substituted phenyl ring and pyrazole ring in the two independent molecules are 86.5 (2) ° and 82.3 (3) °, respectively. The crystal packing displays weak intermolecular C—H···O interactions (Table 1).

Experimental

To a stirred solution of 1-methyl-3-methyl-5-chloro-1H-pyrazole- 4-carbaldehyde(30 mmol) and 3-methylphenol(48 mmol) in DMF(30 ml) was added potassium hydroxide(60 mmol) at room temperature. The resulting mixture was heated to 388 k for 6 h. Then the reaction solution was poured into cold water(100 ml) and extracted with ethyl acetate (3 x 60 ml). The organic layer was dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was recrystallized from ethyl acetate/petroleum ether to give colourless crystals.