(Z)-4-{1-[(2-Hy-droxy-ethyl)-amino]-ethyl-idene}-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

In the title compound C(14)H(17)N(3)O(2), 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 intra-molecular 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 = 259.31

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.173

S = 0.98

2353 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); 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) ▶.

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

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

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

C14H17N3O2	F(000) = 1104
Mr = 259.31	Dx = 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

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

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(Fo2) + (0.1157P)2] where P = (Fo2 + 2Fc2)/3
2353 reflections	(Δ/σ)max = 0.001
176 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)*

	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)

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

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)

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)