4-[(E)-(4-Diethyl­amino-2-hy­droxy­benzyl­idene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

K Manvizhi; G Chakkaravarthi; G Anbalagan; G Rajagopal

doi:10.1107/S1600536811037615

. 2011 Sep 20;67(Pt 10):o2692. doi: 10.1107/S1600536811037615

4-[(E)-(4-Diethylamino-2-hydroxybenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

K Manvizhi ^a, G Chakkaravarthi ^b,^*, G Anbalagan ^c, G Rajagopal ^d,^*

PMCID: PMC3201426 PMID: 22064620

Abstract

In the title compound, C₂₂H₂₆N₄O₂, the phenyl ring and hydroxybenzene group are twisted with respect to the central pyrazolone ring, making dihedral angles of 54.05 (5) and 21.80 (6)°, respectively. One of the ethyl groups is disordered over two positions with site occupancies of 0.872 (6) and 0.128 (6). The molecular structure features short intramolecular O—H⋯N and C—H⋯O contacts. The crystal packing exhibits weak intermolecular C—H⋯O and C—H⋯π interactions.

Related literature

For biological activities of pyrazolone derivatives, see: Gursoy et al. (2000 ▶); Ragavan et al. (2009 ▶). For related structures, see: Wang et al. (2007 ▶); Zhu et al. (2008 ▶).

Experimental

Crystal data

C₂₂H₂₆N₄O₂
M _r = 378.47
Monoclinic,
a = 17.2794 (6) Å
b = 7.1853 (3) Å
c = 32.9711 (12) Å
β = 101.652 (1)°
V = 4009.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.28 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.977, T _max = 0.984
21210 measured reflections
4398 independent reflections
3293 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.126
S = 1.03
4398 reflections
274 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037615/gk2400sup1.cif

e-67-o2692-sup1.cif^{(30.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037615/gk2400Isup2.hkl

e-67-o2692-Isup2.hkl^{(211.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811037615/gk2400Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the N1/N2/C7/C8/C9 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N3	0.82	1.88	2.6127 (17)	148
C12—H12⋯O1	0.93	2.33	3.004 (2)	130
C2—H2⋯O2ⁱ	0.93	2.48	3.267 (2)	142
C11—H11B⋯O1ⁱⁱ	0.96	2.36	3.309 (2)	172
C4—H4⋯Cg2ⁱⁱⁱ	0.93	2.89	3.746 (2)	153
C6—H6⋯Cg1^iv	0.93	2.78	3.559 (2)	142

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

Acknowledgments

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

supplementary crystallographic information

Comment

Pyrazolone derivatives exhibit antipyretic, anti-inflammatory, antibacterial and antifungal (Gursoy et al., 2000; Ragavan et al., 2009) activities. The geometric parameters of the title compound, (Fig. 1) agree well with the reported similar structures (Wang et al., 2007; Zhu et al., 2008).

The phenyl ring (C1–C6) and hydroxybenzene group (C13–C18) are twisted with respect to the pyrazolone ring (N1/N2/C7/C8/C9), making the dihedral angles of and 54.05 (5) and 21.80 (6)°, respectively. One of the ethyl groups is disordered over two positions with site occupancies of 0.872 (6) and 0.128 (6). The molecular structure is stabilized by weak intramolecular O—H···N and C—H···O interactions and the crystal packing exhibits weak intermolecular C—H···O and C—H···π interactions (Table 1 & Fig. 2).

Experimental

A solution of 1-phenyl-2,3-dimethyl-4-amino-3-pyrazolin-5-one (0.203 g, 1 mmol) in ethanol (5 ml) was added to a solution of 4-diethylamino-2-hydroxybenzaldehyde (0.193 g, 1 mmol) in ethanol (5 ml). The reaction mixture was stirred for 2 h at room temperature then heated to reflux for 2 h and kept at 273 K for 4h. The characteristic pale-green precipitate obtained was filtered and recrystallized by dissolving in methanol (m.p. 438 K). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.