4-(4-Chloro­benz­yl)-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one

Shaaban K Mohamed; Mahmoud A A El-Remaily; Ahmed M Soliman; Hossam Abdel-Ghany; Seik Weng Ng

doi:10.1107/S1600536811013791

. 2011 Apr 16;67(Pt 5):o1153. doi: 10.1107/S1600536811013791

4-(4-Chlorobenzyl)-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one

Shaaban K Mohamed ^a, Mahmoud A A El-Remaily ^b, Ahmed M Soliman ^b, Hossam Abdel-Ghany ^b, Seik Weng Ng ^c,^*

PMCID: PMC3089257 PMID: 21754461

Abstract

The five-membered ring of the title compound, C₁₇H₁₅ClN₂O, is almost planar (r.m.s. deviation = 0.008 Å), and its phenyl subsitutent is aligned at 34.9 (1)° with respect to this ring. The angle at the methylene C atom is opened to 116.4 (2)°. In the crystal, adjacent molecules are linked by an N—H⋯O hydrogen bond, generating a linear chain along the a axis.

Related literature

For the synthesis, see: Pettinari et al. (1994 ▶).

Experimental

Crystal data

C₁₇H₁₅ClN₂O
M _r = 298.76
Orthorhombic,
a = 23.1540 (3) Å
b = 43.8905 (6) Å
c = 5.6239 (1) Å
V = 5715.23 (15) Å³
Z = 16
Cu Kα radiation
μ = 2.36 mm⁻¹
T = 100 K
0.30 × 0.30 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.538, T _max = 0.933
10182 measured reflections
2623 independent reflections
2611 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.097
S = 1.08
2623 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.41 e Å⁻³
Absolute structure: Flack (1983 ▶), 1011 Friedel pairs
Flack parameter: 0.000 (12)

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013791/bt5516sup1.cif

e-67-o1153-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013791/bt5516Isup2.hkl

e-67-o1153-Isup2.hkl^{(129.1KB, hkl)}

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
N2—H2⋯O1ⁱ	0.85 (3)	1.82 (3)	2.6516 (18)	165 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank Machester Metropolitan University, Sohag University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

3-Methyl-1-phenyl-4,5-dihydro-1H-5-pyrazolone possesses an active methylene linkage that undergoes condensation with aromatic aldehydes to yield compounds that react with metal salts (Pettinari et al., 1994). In these organic compounds, the pyrazole ring is connected to the aromatic system (of the aldehyde precursor) by a methylene linkage. The five-membered ring of C₁₇H₁₅ClN₂O (Scheme I) is planar, and its phenyl subsitutent is aligned at 34.9 (1) ° with respect to this ring. The angle at the methylene C atom is opened to 116.4 (2) ° (Fig. 1). Adjacent molecules are linked by an N–H···O hydrogen bond to generate a linear chain along the a-axis of the orthorhombic unit cell (Fig. 2).

Experimental

3-Methyl-1-phenyl-4,5-dihydro-1H-5-pyrazolone (10 mmol) and 4-chlorobenzaldehyde (10 mmol) along with few drops of concentrated hydrochloric acid were heated at 426 K in N,N-dimethylformamide (50 ml) for 8 h. The product was collected and recrystallized from ethanol; m.p. 471 K.