(E)-4-(5-Hydr­oxy-2-methyl­benzyl­idene­amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Zheng, Y.-F.; Yang, M.-H.

doi:10.1107/S1600536808029930

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o2017

doi:10.1107/S1600536808029930

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(E)-4-(5-Hydroxy-2-methylbenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Yun-Fa Zheng ^a and Ming-Hua Yang ^a ^*

^aDepartment of Chemistry, Lishui University, Lishui 323000, People's Republic of China
^*Correspondence e-mail: zjlsxyhx@126.com

(Received 15 September 2008; accepted 17 September 2008; online 27 September 2008)

The title compound, C₁₉H₁₉N₃O₂, is a Schiff base compound derived from 4-aminoantipyrine and 5-hydroxy-2-methylbenzaldehyde. The molecule adopts a trans configuration about the central C=N bond. There is an intramolecular O—H⋯N hydrogen bond. Futhermore, weak C—H⋯O hydrogen bonds lead to the formation of a chain developing parallel to the b axis.

Related literature

For related literature, see: Alemi & Shaabani (2000 ); Kim & Shin (1999 ); Yan et al. (2006 ); Zheng et al. (2006 ); You et al. (2006 ).

Experimental

Crystal data

C₁₉H₁₉N₃O₂
M_r = 321.37
Monoclinic, P 2₁ /n
a = 12.030 (2) Å
b = 7.1400 (14) Å
c = 20.210 (4) Å
β = 104.01 (3)°
V = 1684.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.28 × 0.27 × 0.23 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.965, T_max = 0.971
12992 measured reflections
3038 independent reflections
2101 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.117
S = 1.11
3038 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.90	2.6275 (19)	148
C10—H10C⋯O1ⁱ	0.96	2.46	3.386 (2)	163
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808029930/dn2375sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029930/dn2375Isup2.hkl

checkCIF report

Comment top

The design, synthesis, characterization, and properties of Schiff bases and Schiff base complexes. (Yan et al., 2006; Zheng et al., 2006; You et al., 2006) are still of great interest. Schiff bases that have solvent dependent UV/vis spectra (solvatochromicity) can be suitable NLO active materials (Alemi & Shaabani, 2000). They are also useful in asymmetric oxidation of methyl phenyl sulfide (Kim & Shin, 1999).

The molecule adopts trans configuration about the central C=N bond (Fig. 1). There is an intramolecular O-H···N hydrogen bond. Futhermore, weak C-H···O hydrogen bonds lead to the formation of a chain developping parallel to the b axis (Table 1, Fig. 2).

Related literature top

For related literature, see: Alemi & Shaabani (2000); Kim & Shin (1999); Yan et al. (2006); Zheng et al. (2006); You et al. (2006).

Experimental top

Under nitrogen, a mixture of 5-hydroxy-2-methylbenzaldehyde (1.36 g,10 mmol) and 4-amino-1,2-dihydro-1,5-dimethyl -1-phenylpyrazol-3-one (2.03 g, 10 mmol) in absolute ethanol (120 ml) was refluxed for about 3 h to yield a yellow precipitate. The product was collected by vacuum filtration and washed with ethanol. The crude solid was redissolved in CH₂Cl₂ (100 ml) and washed with water (2*10 ml)and brine(10 ml). After dried over Na₂SO₄, the solvent was removed under vacuum, and yellow solid was isolated in yield 92% (3.5 g). Colourless single crystals of the compound suitable for X-ray analysis were grown from CH₂Cl₂ and absolute ethanol(5:1) by slow evaporation of the solvent at room temperature over a period of about a week.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom-labelling scheme. Ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bond is shown as dashed line.
	Fig. 2. Partial packing view showing the formation of the chain through C-H···O hydrogen bondings displayed as dashed line. H atoms not involved in hydrogen bonds have been omitted for clarity. [Symmetry code: (i) x, 1+y, z]

(E)-4-(5-Hydroxy-2-methylbenzylideneamino)-1,5-dimethyl-2-phenyl- 1H-pyrazol-3(2H)-one top

Crystal data top

C₁₉H₁₉N₃O₂	F(000) = 680
M_r = 321.37	D_x = 1.267 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3038 reflections
a = 12.030 (2) Å	θ = 3.0–25.2°
b = 7.1400 (14) Å	µ = 0.08 mm⁻¹
c = 20.210 (4) Å	T = 298 K
β = 104.01 (3)°	Block, colourless
V = 1684.4 (6) Å³	0.28 × 0.27 × 0.23 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	3038 independent reflections
Radiation source: fine-focus sealed tube	2101 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.2°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.965, T_max = 0.971	k = −8→8
12992 measured reflections	l = −24→24

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0593P)² + 0.1685P] where P = (F_o² + 2F_c²)/3
3038 reflections	(Δ/σ)_max = 0.003
220 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₉H₁₉N₃O₂	V = 1684.4 (6) Å³
M_r = 321.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.030 (2) Å	µ = 0.08 mm⁻¹
b = 7.1400 (14) Å	T = 298 K
c = 20.210 (4) Å	0.28 × 0.27 × 0.23 mm
β = 104.01 (3)°

Data collection top

Bruker APEXII area-detector diffractometer	3038 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2101 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.971	R_int = 0.026
12992 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.11	Δρ_max = 0.19 e Å⁻³
3038 reflections	Δρ_min = −0.18 e Å⁻³
220 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.54536 (10)	0.08488 (19)	0.09989 (7)	0.0484 (4)
N2	0.84821 (10)	0.10229 (18)	0.18740 (7)	0.0478 (4)
N3	0.82904 (11)	0.27459 (18)	0.15274 (7)	0.0489 (4)
O1	0.74035 (9)	−0.16626 (16)	0.18989 (7)	0.0607 (4)
O2	0.35066 (11)	0.19101 (19)	0.01845 (7)	0.0721 (4)
H2	0.4177	0.1999	0.0399	0.108*
C1	1.03702 (13)	0.0611 (2)	0.16517 (8)	0.0500 (4)
H1	1.0178	0.1448	0.1289	0.060*
C2	1.14339 (14)	−0.0241 (3)	0.18084 (9)	0.0569 (5)
H2A	1.1959	0.0045	0.1553	0.068*
C3	1.17288 (15)	−0.1505 (3)	0.23369 (11)	0.0659 (5)
H3	1.2445	−0.2076	0.2436	0.079*
C4	1.09553 (15)	−0.1913 (3)	0.27139 (10)	0.0667 (5)
H4	1.1144	−0.2776	0.3068	0.080*
C5	0.98929 (14)	−0.1047 (2)	0.25717 (9)	0.0549 (5)
H5	0.9378	−0.1311	0.2836	0.066*
C6	0.95980 (12)	0.0212 (2)	0.20351 (8)	0.0433 (4)
C7	0.74648 (13)	−0.0029 (2)	0.17136 (9)	0.0469 (4)
C8	0.66180 (13)	0.1204 (2)	0.13035 (8)	0.0454 (4)
C9	0.71364 (13)	0.2853 (2)	0.12208 (8)	0.0472 (4)
C10	0.66222 (17)	0.4584 (2)	0.08666 (11)	0.0650 (5)
H10A	0.5826	0.4372	0.0659	0.097*
H10B	0.7013	0.4912	0.0521	0.097*
H10C	0.6696	0.5588	0.1191	0.097*
C11	0.89730 (16)	0.4347 (2)	0.18612 (10)	0.0618 (5)
H11A	0.8869	0.5390	0.1552	0.093*
H11B	0.9768	0.4006	0.1986	0.093*
H11C	0.8727	0.4689	0.2263	0.093*
C12	0.49748 (13)	−0.0712 (2)	0.10893 (9)	0.0494 (4)
H12	0.5403	−0.1634	0.1362	0.059*
C13	0.37643 (13)	−0.1053 (2)	0.07677 (8)	0.0469 (4)
C14	0.30773 (14)	0.0258 (2)	0.03279 (9)	0.0524 (4)
C15	0.19260 (15)	−0.0150 (3)	0.00338 (9)	0.0630 (5)
H15	0.1475	0.0710	−0.0258	0.076*
C16	0.14615 (15)	−0.1806 (3)	0.01736 (9)	0.0625 (5)
H16	0.0694	−0.2050	−0.0025	0.075*
C17	0.21076 (14)	−0.3139 (3)	0.06057 (9)	0.0581 (5)
C18	0.15794 (18)	−0.4936 (3)	0.07672 (13)	0.0859 (7)
H18A	0.2150	−0.5676	0.1070	0.129*	0.50
H18B	0.1283	−0.5621	0.0353	0.129*	0.50
H18C	0.0968	−0.4660	0.0981	0.129*	0.50
H18D	0.0784	−0.4962	0.0533	0.129*	0.50
H18E	0.1651	−0.5017	0.1250	0.129*	0.50
H18F	0.1966	−0.5978	0.0622	0.129*	0.50
C19	0.32577 (13)	−0.2731 (2)	0.08928 (9)	0.0546 (4)
H19	0.3703	−0.3611	0.1178	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0449 (8)	0.0456 (8)	0.0570 (8)	0.0014 (6)	0.0167 (6)	−0.0045 (6)
N2	0.0432 (7)	0.0360 (7)	0.0657 (9)	−0.0001 (6)	0.0162 (6)	0.0038 (6)
N3	0.0522 (8)	0.0338 (7)	0.0632 (9)	−0.0023 (6)	0.0190 (7)	0.0010 (6)
O1	0.0527 (7)	0.0390 (7)	0.0894 (9)	−0.0031 (5)	0.0155 (6)	0.0106 (6)
O2	0.0633 (8)	0.0671 (9)	0.0836 (10)	0.0044 (7)	0.0131 (7)	0.0225 (7)
C1	0.0485 (9)	0.0541 (10)	0.0469 (9)	−0.0024 (8)	0.0108 (7)	−0.0004 (8)
C2	0.0462 (9)	0.0640 (12)	0.0617 (11)	−0.0030 (8)	0.0157 (8)	−0.0062 (9)
C3	0.0460 (10)	0.0657 (13)	0.0818 (14)	0.0045 (9)	0.0072 (9)	0.0020 (11)
C4	0.0594 (11)	0.0615 (12)	0.0729 (13)	0.0021 (9)	0.0040 (9)	0.0177 (10)
C5	0.0528 (10)	0.0541 (11)	0.0582 (11)	−0.0057 (8)	0.0139 (8)	0.0056 (9)
C6	0.0412 (8)	0.0386 (9)	0.0492 (9)	−0.0047 (7)	0.0092 (7)	−0.0046 (7)
C7	0.0444 (9)	0.0396 (9)	0.0596 (10)	−0.0003 (7)	0.0180 (7)	−0.0028 (8)
C8	0.0449 (9)	0.0402 (9)	0.0543 (10)	0.0023 (7)	0.0182 (7)	−0.0031 (7)
C9	0.0494 (9)	0.0414 (9)	0.0536 (10)	0.0036 (7)	0.0176 (7)	−0.0031 (7)
C10	0.0704 (12)	0.0459 (11)	0.0794 (13)	0.0078 (9)	0.0196 (10)	0.0107 (9)
C11	0.0649 (11)	0.0410 (10)	0.0824 (13)	−0.0108 (8)	0.0234 (10)	−0.0065 (9)
C12	0.0448 (9)	0.0455 (10)	0.0584 (10)	0.0048 (7)	0.0137 (7)	−0.0030 (8)
C13	0.0424 (8)	0.0487 (10)	0.0507 (9)	0.0034 (7)	0.0135 (7)	−0.0051 (8)
C14	0.0536 (10)	0.0530 (11)	0.0520 (10)	0.0042 (8)	0.0152 (8)	0.0028 (8)
C15	0.0528 (10)	0.0784 (14)	0.0532 (11)	0.0096 (10)	0.0042 (8)	0.0047 (10)
C16	0.0475 (10)	0.0798 (14)	0.0563 (11)	−0.0026 (9)	0.0051 (8)	−0.0087 (10)
C17	0.0498 (9)	0.0611 (11)	0.0628 (11)	−0.0055 (9)	0.0122 (8)	−0.0103 (9)
C18	0.0655 (13)	0.0754 (15)	0.1124 (18)	−0.0206 (11)	0.0128 (12)	−0.0031 (13)
C19	0.0469 (9)	0.0509 (10)	0.0647 (11)	0.0027 (8)	0.0108 (8)	−0.0023 (9)

Geometric parameters (Å, º) top

N1—C12	1.288 (2)	C10—H10A	0.9600
N1—C8	1.410 (2)	C10—H10B	0.9600
N2—C7	1.405 (2)	C10—H10C	0.9600
N2—N3	1.4068 (18)	C11—H11A	0.9600
N2—C6	1.425 (2)	C11—H11B	0.9600
N3—C9	1.379 (2)	C11—H11C	0.9600
N3—C11	1.472 (2)	C12—C13	1.464 (2)
O1—C7	1.2330 (19)	C12—H12	0.9300
O2—C14	1.347 (2)	C13—C19	1.395 (2)
O2—H2	0.8200	C13—C14	1.412 (2)
C1—C6	1.376 (2)	C14—C15	1.399 (2)
C1—C2	1.383 (2)	C15—C16	1.366 (3)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.378 (3)	C16—C17	1.394 (3)
C2—H2A	0.9300	C16—H16	0.9300
C3—C4	1.369 (3)	C17—C19	1.395 (2)
C3—H3	0.9300	C17—C18	1.503 (3)
C4—C5	1.386 (3)	C18—H18A	0.9600
C4—H4	0.9300	C18—H18B	0.9600
C5—C6	1.387 (2)	C18—H18C	0.9600
C5—H5	0.9300	C18—H18D	0.9600
C7—C8	1.446 (2)	C18—H18E	0.9600
C8—C9	1.361 (2)	C18—H18F	0.9600
C9—C10	1.486 (2)	C19—H19	0.9300

C12—N1—C8	121.67 (14)	H11A—C11—H11C	109.5
C7—N2—N3	108.89 (12)	H11B—C11—H11C	109.5
C7—N2—C6	123.74 (13)	N1—C12—C13	120.77 (15)
N3—N2—C6	120.05 (12)	N1—C12—H12	119.6
C9—N3—N2	107.34 (12)	C13—C12—H12	119.6
C9—N3—C11	123.52 (14)	C19—C13—C14	117.94 (15)
N2—N3—C11	116.40 (13)	C19—C13—C12	119.56 (15)
C14—O2—H2	109.5	C14—C13—C12	122.50 (16)
C6—C1—C2	119.58 (16)	O2—C14—C15	118.85 (16)
C6—C1—H1	120.2	O2—C14—C13	121.29 (15)
C2—C1—H1	120.2	C15—C14—C13	119.86 (17)
C3—C2—C1	121.07 (18)	C16—C15—C14	120.31 (17)
C3—C2—H2A	119.5	C16—C15—H15	119.8
C1—C2—H2A	119.5	C14—C15—H15	119.8
C4—C3—C2	119.25 (17)	C15—C16—C17	121.76 (17)
C4—C3—H3	120.4	C15—C16—H16	119.1
C2—C3—H3	120.4	C17—C16—H16	119.1
C3—C4—C5	120.45 (18)	C16—C17—C19	117.67 (17)
C3—C4—H4	119.8	C16—C17—C18	121.21 (17)
C5—C4—H4	119.8	C19—C17—C18	121.12 (18)
C4—C5—C6	119.99 (17)	C17—C18—H18A	109.5
C4—C5—H5	120.0	C17—C18—H18B	109.5
C6—C5—H5	120.0	H18A—C18—H18B	109.5
C1—C6—C5	119.64 (15)	C17—C18—H18C	109.5
C1—C6—N2	120.95 (15)	H18A—C18—H18C	109.5
C5—C6—N2	119.37 (14)	H18B—C18—H18C	109.5
O1—C7—N2	123.25 (15)	C17—C18—H18D	109.5
O1—C7—C8	131.64 (15)	H18A—C18—H18D	141.1
N2—C7—C8	105.10 (14)	H18B—C18—H18D	56.3
C9—C8—N1	122.57 (15)	H18C—C18—H18D	56.3
C9—C8—C7	108.46 (14)	C17—C18—H18E	109.5
N1—C8—C7	128.93 (15)	H18A—C18—H18E	56.3
C8—C9—N3	109.78 (14)	H18B—C18—H18E	141.1
C8—C9—C10	128.96 (15)	H18C—C18—H18E	56.3
N3—C9—C10	121.26 (15)	H18D—C18—H18E	109.5
C9—C10—H10A	109.5	C17—C18—H18F	109.5
C9—C10—H10B	109.5	H18A—C18—H18F	56.3
H10A—C10—H10B	109.5	H18B—C18—H18F	56.3
C9—C10—H10C	109.5	H18C—C18—H18F	141.1
H10A—C10—H10C	109.5	H18D—C18—H18F	109.5
H10B—C10—H10C	109.5	H18E—C18—H18F	109.5
N3—C11—H11A	109.5	C13—C19—C17	122.45 (16)
N3—C11—H11B	109.5	C13—C19—H19	118.8
H11A—C11—H11B	109.5	C17—C19—H19	118.8
N3—C11—H11C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.90	2.6275 (19)	148
C10—H10C···O1ⁱ	0.96	2.46	3.386 (2)	163

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉N₃O₂
M_r	321.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	12.030 (2), 7.1400 (14), 20.210 (4)
β (°)	104.01 (3)
V (Å³)	1684.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.28 × 0.27 × 0.23

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.965, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	12992, 3038, 2101
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.117, 1.11
No. of reflections	3038
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.90	2.6275 (19)	147.6
C10—H10C···O1ⁱ	0.96	2.46	3.386 (2)	162.8

Symmetry code: (i) x, y+1, z.

Acknowledgements

The authors are grateful to the Natural Science Foundation of Zhejiang Province (No. Y407081) for financial support.

References

Alemi, A. A. & Shaabani, B. (2000). Acta Chim. Slov. 47, 363–369. CAS Google Scholar
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Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 64| Part 10| October 2008| Page o2017

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(E)-4-(5-Hydr­­oxy-2-methyl­benzyl­­idene­amino)-1,5-di­methyl-2-phenyl-1H-pyrazol-3(2H)-one

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(E)-4-(5-Hydroxy-2-methylbenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one