(Z)-4-{1-[(2-Hy­droxy­ethyl)­amino]­ethyl­idene}-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Jayarajan, R.; Sharmila, P.; Jagadeesan, G.; Vasuki, G.; Aravindhan, S.

doi:10.1107/S1600536810054127

organic compounds

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doi:10.1107/S1600536810054127

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(Z)-4-{1-[(2-Hydroxyethyl)amino]ethylidene}-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

R. Jayarajan,^a P. Sharmila,^b G. Jagadeesan,^b G. Vasuki ^a and S. Aravindhan ^b ^*

^aDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India, and ^bDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: aravindhanpresidency@gmail.com

(Received 17 November 2010; accepted 24 December 2010; online 22 January 2011)

In the title compound C₁₄H₁₇N₃O₂, the dihedral angle between the rings is 16.68 (13)°. Although the compound crystallizes in the keto form, the possibility of keto-enamine–enol-imine tautomerism is explained by a strong intramolecular N—H⋯O hydrogen bond.

Related literature

4-Acylpyrazolones are good chelating ligands and also show antibacterial, antifungal, anti-inflammatory, carcino-static and enzyme inhibitory activity, see: Patel et al. (2000 , 2001 ); Chohan & Kausar (2000 ); Chohan, Jaffery & Supuran (2001 ); Chohan, Munawar & Supuran (2001 ); Chohan et al. (2002); Yang et al. (2000 ). For analgesic agents, see: Gursoy et al. (2000 ).

Experimental

Crystal data

C₁₄H₁₇N₃O₂
M_r = 259.31
Monoclinic, C 2/c
a = 22.4703 (13) Å
b = 7.0902 (4) Å
c = 18.0565 (11) Å
β = 110.926 (7)°
V = 2687.0 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 273 K
0.20 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.978, T_max = 0.982
4492 measured reflections
2353 independent reflections
1544 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.173
S = 0.98
2353 reflections
176 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H⋯O1	0.90 (3)	1.92 (3)	2.711 (3)	146 (3)

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054127/ds2072sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054127/ds2072Isup2.hkl

checkCIF report

Comment top

The ORTEP diagram for the molecule of the title compound is given in Fig:1. The molecule is almost planar where the phenyl ring is tilted by 17.66° to the rest of the molecule. The planarity is explained by the torsion angles C3—C4—C13—N3(-179.49°) and C13—N3—C15—C16 (173.88°).

The hydroxyl oxygen (O2) shows disorder and hence O2A and O2B were not refined using anisotropic thermal parameters.This disordered nature show a dynamic rotation about C15—C16 single bond.

The hydrogen (H3) of the imino group(N3) forms a strong intra-molecular hydrogen bond with keto oxygen O1 (2.711 Å, 146.56°). Along with this, the double bond character of C13—N3, show the possibility of proton shuttling between O1 and N3.

Though phenyl ring and pyrazol ring can adopt perpendicularity,the weak C11—H11···O1 interaction (2.954 Å, 121.13°) keeps them with near planarity.

The crystal packing diagram in Fig:2.

Related literature top

4-Acylpyrazolones are good chelating ligands and also show antibacterial, antifungal, anti-inflammatory, carcino-static and enzyme inhibitory activity, see: Patel et al. (2000, 2001); Chohan & Kausar (2000); Chohan, Jaffery & Supuran (2001); Chohan, Munawar & Supuran (2001); Chohan et al. (2002); Yang et al. (2000). For related literature [on what subject?], see: Gursoy et al. (2000).

Experimental top

Ethanolic solution of 3-methyl-1-phenyl-4-acetylpyrazolin-5-ol (0.432 g, 2 mmol) and 2-aminoethanol (0.122 g, 2mmoL) were taken in a round bottom flask and refluxed for 4 h. The solid product was filtered and washed with cold ethanol. The product obtained was pure by TLC and NMR spectroscopy. However, the product was further purified by re-crystallization from ethanol and dried under vacuum. The compound was crystallized by slow evaporation technique using methanol as solvent at room temperature.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The ORTEP diagram of molecule H-atoms are involved in hydrogen bonding are shown as Dashed lines.
	Fig. 2. Crystal Packing Diagram.

(Z)-4-{1-[(2-Hydroxyethyl)amino]ethylidene}-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one top

Crystal data top

C₁₄H₁₇N₃O₂	F(000) = 1104
M_r = 259.31	D_x = 1.282 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2447 reflections
a = 22.4703 (13) Å	θ = 2.7–29.3°
b = 7.0902 (4) Å	µ = 0.09 mm⁻¹
c = 18.0565 (11) Å	T = 273 K
β = 110.926 (7)°	Monoclinic, colourless
V = 2687.0 (3) Å³	0.20 × 0.20 × 0.20 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2353 independent reflections
Radiation source: fine-focus sealed tube	1544 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 15.9821 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
ω scans	h = −26→26
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −8→4
T_min = 0.978, T_max = 0.982	l = −19→21
4492 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.1157P)²] where P = (F_o² + 2F_c²)/3
2353 reflections	(Δ/σ)_max = 0.001
176 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₇N₃O₂	V = 2687.0 (3) Å³
M_r = 259.31	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.4703 (13) Å	µ = 0.09 mm⁻¹
b = 7.0902 (4) Å	T = 273 K
c = 18.0565 (11) Å	0.20 × 0.20 × 0.20 mm
β = 110.926 (7)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2353 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	1544 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.982	R_int = 0.026
4492 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.46 e Å⁻³
2353 reflections	Δρ_min = −0.24 e Å⁻³
176 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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)
O1	−0.05676 (8)	0.3364 (3)	0.35564 (9)	0.0534 (5)
N1	−0.11378 (9)	0.2982 (3)	0.44012 (10)	0.0384 (5)
N2	−0.10103 (10)	0.2539 (3)	0.51998 (10)	0.0439 (5)
C11	−0.19444 (10)	0.4030 (3)	0.31598 (12)	0.0432 (6)
H11	−0.1628	0.4457	0.2982	0.052*
C10	−0.25819 (11)	0.4237 (4)	0.26886 (14)	0.0523 (7)
H10	−0.2690	0.4794	0.2192	0.063*
N3	0.06883 (10)	0.2770 (3)	0.43754 (13)	0.0500 (6)
C6	−0.17841 (10)	0.3190 (3)	0.38911 (12)	0.0378 (6)
C4	−0.00882 (11)	0.2571 (3)	0.49473 (13)	0.0382 (6)
C9	−0.30523 (12)	0.3635 (4)	0.29449 (15)	0.0586 (8)
H9	−0.3478	0.3793	0.2628	0.070*
C13	0.05492 (11)	0.2441 (3)	0.50051 (13)	0.0397 (6)
C14	0.10798 (12)	0.1939 (4)	0.57534 (14)	0.0539 (7)
H14A	0.1475	0.1930	0.5661	0.081*
H14B	0.1004	0.0711	0.5926	0.081*
H14C	0.1103	0.2852	0.6155	0.081*
C8	−0.28911 (13)	0.2791 (4)	0.36768 (16)	0.0627 (8)
H8	−0.3210	0.2374	0.3852	0.075*
C3	−0.03936 (12)	0.2315 (3)	0.55172 (13)	0.0413 (6)
C7	−0.22638 (12)	0.2558 (4)	0.41503 (14)	0.0510 (7)
H7	−0.2159	0.1980	0.4643	0.061*
C5	−0.05950 (11)	0.3010 (3)	0.42224 (12)	0.0379 (6)
C12	−0.01114 (13)	0.1893 (4)	0.63896 (13)	0.0569 (7)
H12A	−0.0446	0.1807	0.6602	0.085*
H12B	0.0177	0.2884	0.6654	0.085*
H12C	0.0115	0.0718	0.6470	0.085*
C16	0.12548 (15)	0.2950 (5)	0.34639 (18)	0.0694 (9)
C15	0.13080 (13)	0.2678 (5)	0.42954 (18)	0.0677 (8)
H15A	0.1501	0.1461	0.4481	0.081*
H15B	0.1583	0.3644	0.4624	0.081*
O2A	0.08008 (17)	0.1945 (5)	0.2936 (2)	0.0683 (13)*	0.567 (5)
O2B	0.0870 (2)	0.4236 (7)	0.3041 (3)	0.0637 (16)*	0.433 (5)
H	0.0343 (14)	0.315 (4)	0.3970 (16)	0.063 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0487 (10)	0.0768 (13)	0.0344 (9)	0.0027 (9)	0.0143 (8)	0.0094 (8)
N1	0.0392 (11)	0.0452 (11)	0.0299 (10)	0.0004 (8)	0.0115 (8)	0.0011 (8)
N2	0.0461 (12)	0.0548 (13)	0.0294 (10)	−0.0018 (9)	0.0116 (9)	0.0022 (9)
C11	0.0442 (13)	0.0431 (13)	0.0410 (13)	−0.0009 (11)	0.0135 (11)	−0.0001 (10)
C10	0.0544 (15)	0.0531 (15)	0.0421 (14)	0.0072 (12)	0.0084 (12)	0.0011 (12)
N3	0.0375 (12)	0.0651 (15)	0.0450 (13)	0.0036 (10)	0.0120 (10)	0.0048 (11)
C6	0.0441 (13)	0.0344 (12)	0.0336 (12)	0.0012 (10)	0.0122 (10)	−0.0046 (10)
C4	0.0437 (13)	0.0346 (12)	0.0323 (12)	−0.0009 (10)	0.0087 (10)	0.0005 (10)
C9	0.0436 (14)	0.077 (2)	0.0485 (16)	0.0075 (13)	0.0083 (12)	−0.0075 (14)
C13	0.0467 (14)	0.0324 (12)	0.0356 (13)	−0.0027 (10)	0.0093 (11)	−0.0034 (10)
C14	0.0487 (15)	0.0547 (15)	0.0471 (15)	−0.0001 (12)	0.0035 (12)	−0.0006 (12)
C8	0.0467 (16)	0.092 (2)	0.0538 (17)	−0.0024 (14)	0.0234 (13)	−0.0078 (15)
C3	0.0489 (14)	0.0369 (13)	0.0350 (12)	−0.0027 (10)	0.0110 (11)	−0.0003 (10)
C7	0.0445 (14)	0.0710 (19)	0.0388 (14)	−0.0002 (13)	0.0163 (12)	−0.0012 (12)
C5	0.0443 (13)	0.0381 (12)	0.0310 (12)	−0.0007 (10)	0.0131 (10)	0.0014 (9)
C12	0.0632 (17)	0.0698 (18)	0.0328 (13)	−0.0007 (14)	0.0110 (12)	0.0068 (12)
C16	0.0639 (18)	0.091 (2)	0.0568 (18)	−0.0034 (17)	0.0262 (15)	0.0007 (17)
C15	0.0434 (16)	0.094 (2)	0.0663 (19)	0.0048 (14)	0.0208 (14)	0.0060 (16)

Geometric parameters (Å, º) top

O1—C5	1.251 (3)	C9—H9	0.9300
N1—C5	1.369 (3)	C13—C14	1.491 (3)
N1—N2	1.402 (2)	C14—H14A	0.9600
N1—C6	1.423 (3)	C14—H14B	0.9600
N2—C3	1.306 (3)	C14—H14C	0.9600
C11—C6	1.374 (3)	C8—C7	1.373 (3)
C11—C10	1.388 (3)	C8—H8	0.9300
C11—H11	0.9300	C3—C12	1.503 (3)
C10—C9	1.365 (4)	C7—H7	0.9300
C10—H10	0.9300	C12—H12A	0.9600
N3—C13	1.303 (3)	C12—H12B	0.9600
N3—C15	1.452 (4)	C12—H12C	0.9600
N3—H	0.90 (3)	C16—O2B	1.300 (5)
C6—C7	1.394 (4)	C16—O2A	1.328 (4)
C4—C13	1.401 (4)	C16—C15	1.476 (4)
C4—C3	1.438 (3)	C15—H15A	0.9700
C4—C5	1.429 (3)	C15—H15B	0.9700
C9—C8	1.376 (4)

C5—N1—N2	111.97 (17)	H14A—C14—H14C	109.5
C5—N1—C6	129.44 (18)	H14B—C14—H14C	109.5
N2—N1—C6	118.40 (18)	C7—C8—C9	120.7 (3)
C3—N2—N1	105.88 (18)	C7—C8—H8	119.7
C6—C11—C10	119.6 (2)	C9—C8—H8	119.7
C6—C11—H11	120.2	N2—C3—C4	111.9 (2)
C10—C11—H11	120.2	N2—C3—C12	117.9 (2)
C9—C10—C11	120.9 (2)	C4—C3—C12	130.1 (2)
C9—C10—H10	119.5	C8—C7—C6	119.8 (2)
C11—C10—H10	119.5	C8—C7—H7	120.1
C13—N3—C15	128.0 (2)	C6—C7—H7	120.1
C13—N3—H	111.0 (18)	O1—C5—N1	125.7 (2)
C15—N3—H	120.9 (18)	O1—C5—C4	128.8 (2)
C11—C6—C7	119.6 (2)	N1—C5—C4	105.45 (19)
C11—C6—N1	121.6 (2)	C3—C12—H12A	109.5
C7—C6—N1	118.8 (2)	C3—C12—H12B	109.5
C13—C4—C3	132.4 (2)	H12A—C12—H12B	109.5
C13—C4—C5	122.8 (2)	C3—C12—H12C	109.5
C3—C4—C5	104.8 (2)	H12A—C12—H12C	109.5
C10—C9—C8	119.4 (2)	H12B—C12—H12C	109.5
C10—C9—H9	120.3	O2B—C16—O2A	77.0 (3)
C8—C9—H9	120.3	O2B—C16—C15	119.0 (3)
N3—C13—C4	118.7 (2)	O2A—C16—C15	114.9 (3)
N3—C13—C14	118.0 (2)	N3—C15—C16	111.3 (2)
C4—C13—C14	123.3 (2)	N3—C15—H15A	109.4
C13—C14—H14A	109.5	C16—C15—H15A	109.4
C13—C14—H14B	109.5	N3—C15—H15B	109.4
H14A—C14—H14B	109.5	C16—C15—H15B	109.4
C13—C14—H14C	109.5	H15A—C15—H15B	108.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H···O1	0.90 (3)	1.92 (3)	2.711 (3)	146 (3)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₇N₃O₂
M_r	259.31
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	273
a, b, c (Å)	22.4703 (13), 7.0902 (4), 18.0565 (11)
β (°)	110.926 (7)
V (Å³)	2687.0 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.978, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	4492, 2353, 1544
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.173, 0.98
No. of reflections	2353
No. of parameters	176
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.24

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H···O1	0.90 (3)	1.92 (3)	2.711 (3)	146 (3)

Acknowledgements

RJ thanks the UGC, India, for the award of Rajiv Gandhi National Fellowship. GV thanks the UGC, India, and the DST–India (Green Chemistry open-ended project) for financial assistance and the DST–FIST for the single crystal X-ray facility at the Department of Chemistry, Pondicherry University, Puducherry.

References

Chohan, Z. H., Jaffery, M. F. & Supuran, C. T. (2001). Met. Based Drugs. 8, 95–101. CrossRef PubMed CAS Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(Z)-4-{1-[(2-Hy­dr­oxy­ethyl)­amino]­ethyl­­idene}-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(Z)-4-{1-[(2-Hydroxyethyl)amino]ethylidene}-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one