1-(4-Chloro­phen­yl)-3-phenyl-1H-pyrazol-5(4H)-one

Yong-Jie Ding; Chun-Xiang Zhao

doi:10.1107/S1600536809055263

. 2010 Feb 27;66(Pt 3):o709. doi: 10.1107/S1600536809055263

1-(4-Chlorophenyl)-3-phenyl-1H-pyrazol-5(4H)-one

Yong-Jie Ding ^a, Chun-Xiang Zhao ^b,^*

PMCID: PMC2983571 PMID: 21580447

Abstract

In the crystal of the title compound, C₁₅H₁₁ClN₂O, the molecules are linked by C—H⋯O and weak C—H⋯π interactions. The chlorophenyl and phenyl rings are twisted with respect to the central pyrazolone ring, making dihedral angles of 18.23 (8) and 8.35 (8)°, respectively. The N—N and C=O bond lengths are comparable to those reported for pyrazolone compounds.

Related literature

For the properties and applications of pyrazolones and their derivatives, see: Bao et al. (2006 ▶); Bose et al. (2005 ▶); Ito et al. (2001 ▶); Li et al. (2000 ▶); Shi, et al. (2005 ▶); Whitaker (1995 ▶). For the synthesis, see: Jensen (1959 ▶). For related structures, see: Bovio et al. (1974 ▶); Dardonville et al. (1998 ▶); Ferretti et al. (1985 ▶); Holzer et al. (1999 ▶).

Experimental

Crystal data

C₁₅H₁₁ClN₂O
M _r = 270.71
Monoclinic,
a = 11.2593 (4) Å
b = 12.1848 (4) Å
c = 9.5498 (3) Å
β = 103.053 (1)°
V = 1276.31 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 296 K
0.32 × 0.28 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
17039 measured reflections
3172 independent reflections
2578 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.111
S = 1.04
3172 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809055263/dn2522sup1.cif

e-66-0o709-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055263/dn2522Isup2.hkl

e-66-0o709-Isup2.hkl^{(155.6KB, hkl)}

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

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

Cg1 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O1ⁱ	0.97	2.40	3.3115 (19)	156
C8—H8A⋯Cg1ⁱⁱ	0.97	2.76	3.5026 (17)	134

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

Table 2. Comparison of C=O and N—N bond lengths (Å) between the title compound and reported pyrazolone compounds.

Compound	C=O	N—N
C₁₃H₁₄N₂O₂^a	1.313 (2)	1.395 (2)
C₁₉H₁₆N₂O₂^a	1.261 (2)	1.404 (2)
C₁₅H₁₂N₂O₂S^a	1.246 (2)	1.373 (2)
C₂₂H₁₅ClN₂O^c	1.228 (2)	1.405 (2)
C₁₆H₁₁N₃O^c	1.252 (3)	1.412 (4)
C₁₆H₁₀ClN₃O^c	1.250 (5)	1.420 (5)
C₁₀H₈N₄O₅^d	1.207 (3)	1.412 (2)
C₁₅H₁₁ClN₂O^e	1.213 (2)	1.404 (2)

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Notes: (a) Holzer et al. (1999 ▶); (b) Bovio et al. (1974 ▶); (c) Ferretti et al. (1985 ▶); (d) Dardonville et al. (1998 ▶); (e) this work.

Acknowledgments

The authors gratefully acknowledge financial support by the Scientific Research Innovation Foundation for youth teachers of Zhoukou Normal University

supplementary crystallographic information

Comment

Pyrazolones and their derivatives constitute a group of organic compounds that have been extensively studied due to their diverse properties and applications. For example, many more applications have been devised for this group of molecules in the pharmaceutical field. Moreover, they have been applied to the solvent extraction of metal ions (Bose et al., 2005), for analytical purposes (Ito et al., 2001), in the preparation of azo colorants (Whitaker, 1995), as ligands in complexes with catalytic activity (Bao et al., 2006) and in the synthesis of rare earth metal complexes with interesting photophysical properties (Shi et al., 2005). Also, it is important in understanding the behaviour of these compounds with respect to the mechanisms of pharmacological activities (Li et al., 2000). In order to expand this field, the novel title compound (I) has been synthesized, and its crystal structure is reported herein for the first time.

The asymmetric unit of the title compound is built up from a central pyrazolone ring substituted in 1,3 by a 4-chlorophenyl and a phenyl rings (Fig. 1). The chlorophenyl and phenyl rings are slightly twisted with respect to the central pyrazolone ring making dihedral angles of 18.23 (8)° and 8.35 (8)° respectively, thus indicating a high degree of conjugation and electron delocalization.The N(1)–N(2) and C(7)=O(1) distances are comparable, within experimental errors, with related pyrazolones reported in the literature (Table 2).

The cohesion of the crystal is assured by weak C-H···O and C-H···π interactions (Table 1).

Experimental

All reagents were obtained from commercial sources and used without further purification. 1-(4-chlorophenyl)-3-phenyl-1H-pyrazol-5(4H)-one was synthesized according to the method proposed by Jensen (1959). (yield 84.5%; m.p. 435–436 K). Analysis required for C₁₅H₁₁ClN₂O: C 66.55%, H 4.10%, N10.35%; found: C 66.51, H 4.08, N 10.41%. Block-like golden single crystals of CPP were grown from ethanol by slow evaporation over a period of several weeks.