3-Oxo-5-(piperidin-1-yl)-2,3-dihydro-1H-pyrazole-4-carbonitrile.

In the title compound, C(9)H(12)N(4)O, the piperidine ring adopts a chair conformation and makes a dihedral angle of 42.49 (11)° with the approximately planar pyrazole moiety [maximum deviation = 0.038 (2) Å]. In the crystal, N-H⋯O and N-H⋯N hydrogen bonds and a weak C-H⋯O inter-action link the mol-ecules into sheets lying parallel to (110).

Related literature

For pharmacological background, see: Patel et al. (1990 ▶); Morimoto et al. (1990 ▶). For related structures see: Zaharan et al. (2001 ▶); Elgemeie et al. (2007 ▶); Gouda et al. (2010 ▶); Shelton et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H12N4O

M = 192.23

Triclinic,

a = 7.2667 (5) Å

b = 7.9624 (5) Å

c = 8.8306 (8) Å

α = 89.280 (6)°

β = 75.934 (7)°

γ = 71.906 (6)°

V = 470.01 (6) Å3

Z = 2

Cu Kα radiation

μ = 0.77 mm−1

T = 150 K

0.22 × 0.19 × 0.13 mm

Data collection

Oxford Diffraction Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.849, T max = 0.906

5083 measured reflections

1803 independent reflections

1627 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.166

S = 1.11

1803 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.61 e Å−3

Data collection: Gemini User Manual (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2002 ▶); data reduction: CrysAlis RED; 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: SHELXTL, PARST (Nardelli, 1995 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047714/hb6450sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047714/hb6450Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047714/hb6450Isup3.cml

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

C9H12N4O	Z = 2
Mr = 192.23	F(000) = 204
Triclinic, P1	Dx = 1.358 Mg m−3
Hall symbol: -P 1	Melting point: 527 K
a = 7.2667 (5) Å	Cu Kα radiation, λ = 1.54178 Å
b = 7.9624 (5) Å	Cell parameters from 3129 reflections
c = 8.8306 (8) Å	θ = 5–71°
α = 89.280 (6)°	µ = 0.77 mm−1
β = 75.934 (7)°	T = 150 K
γ = 71.906 (6)°	Block, colourless
V = 470.01 (6) Å3	0.22 × 0.19 × 0.13 mm

Oxford Diffraction Gemini diffractometer	1803 independent reflections
Radiation source: fine-focus sealed tube	1627 reflections with I > 2σ(I)
graphite	Rint = 0.013
ω/2θ scans	θmax = 70.9°, θmin = 5.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	h = −8→8
Tmin = 0.849, Tmax = 0.906	k = −9→9
5083 measured reflections	l = −10→10

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0971P)2 + 0.2641P] where P = (Fo2 + 2Fc2)/3
1803 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.61 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K.Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107.

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
O1	1.2334 (2)	0.03312 (18)	0.39572 (17)	0.0334 (4)
N1	0.8756 (2)	0.6211 (2)	0.2901 (2)	0.0306 (4)
N2	0.8011 (2)	0.3667 (2)	0.38329 (19)	0.0273 (4)
H2	0.6730	0.4130	0.4070	0.033*
N3	0.9078 (2)	0.1884 (2)	0.39566 (19)	0.0285 (4)
H3	0.8563	0.1043	0.4146	0.034*
N4	1.4774 (3)	0.3703 (3)	0.2487 (2)	0.0397 (5)
C1	1.0124 (3)	0.7167 (3)	0.2139 (3)	0.0349 (5)
H1A	1.1496	0.6418	0.2014	0.042*
H1B	0.9907	0.8218	0.2789	0.042*
C2	0.9771 (4)	0.7692 (3)	0.0547 (3)	0.0394 (5)
H2A	1.0165	0.6635	−0.0144	0.047*
H2B	1.0596	0.8413	0.0094	0.047*
C3	0.7585 (4)	0.8722 (3)	0.0673 (3)	0.0424 (6)
H3A	0.7234	0.9851	0.1253	0.051*
H3B	0.7386	0.8954	−0.0366	0.051*
C4	0.6237 (3)	0.7685 (3)	0.1497 (3)	0.0380 (5)
H4A	0.4847	0.8390	0.1628	0.046*
H4B	0.6491	0.6610	0.0865	0.046*
C5	0.6632 (3)	0.7218 (3)	0.3084 (2)	0.0333 (5)
H5A	0.6282	0.8293	0.3742	0.040*
H5B	0.5808	0.6517	0.3588	0.040*
C6	0.9374 (3)	0.4540 (2)	0.3267 (2)	0.0249 (4)
C7	1.1293 (3)	0.3363 (2)	0.3210 (2)	0.0252 (4)
C8	1.1054 (3)	0.1702 (2)	0.3729 (2)	0.0262 (4)
C9	1.3185 (3)	0.3601 (3)	0.2816 (2)	0.0289 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0258 (7)	0.0273 (7)	0.0420 (8)	−0.0030 (6)	−0.0067 (6)	0.0098 (6)
N1	0.0276 (9)	0.0285 (9)	0.0356 (9)	−0.0062 (7)	−0.0116 (7)	0.0092 (7)
N2	0.0200 (8)	0.0254 (8)	0.0343 (9)	−0.0032 (6)	−0.0082 (6)	0.0071 (6)
N3	0.0254 (8)	0.0232 (8)	0.0371 (9)	−0.0070 (7)	−0.0092 (7)	0.0072 (6)
N4	0.0283 (10)	0.0412 (11)	0.0545 (11)	−0.0131 (8)	−0.0169 (8)	0.0118 (8)
C1	0.0353 (11)	0.0276 (10)	0.0462 (12)	−0.0126 (9)	−0.0152 (9)	0.0095 (9)
C2	0.0445 (13)	0.0297 (11)	0.0387 (12)	−0.0095 (9)	−0.0038 (9)	0.0084 (9)
C3	0.0532 (14)	0.0321 (11)	0.0331 (11)	−0.0007 (10)	−0.0116 (10)	0.0076 (9)
C4	0.0364 (11)	0.0332 (11)	0.0388 (11)	0.0013 (9)	−0.0154 (9)	0.0018 (9)
C5	0.0295 (11)	0.0274 (10)	0.0382 (11)	−0.0016 (8)	−0.0093 (8)	0.0061 (8)
C6	0.0271 (10)	0.0274 (10)	0.0215 (8)	−0.0078 (8)	−0.0095 (7)	0.0035 (7)
C7	0.0244 (9)	0.0259 (10)	0.0257 (9)	−0.0066 (7)	−0.0090 (7)	0.0029 (7)
C8	0.0255 (9)	0.0261 (9)	0.0252 (9)	−0.0050 (7)	−0.0071 (7)	0.0016 (7)
C9	0.0298 (11)	0.0269 (10)	0.0318 (10)	−0.0070 (8)	−0.0141 (8)	0.0065 (8)

O1—C8	1.246 (2)	C2—H2A	0.9700
N1—C6	1.329 (3)	C2—H2B	0.9700
N1—C1	1.467 (3)	C3—C4	1.520 (3)
N1—C5	1.471 (3)	C3—H3A	0.9700
N2—C6	1.376 (2)	C3—H3B	0.9700
N2—N3	1.408 (2)	C4—C5	1.517 (3)
N2—H2	0.8600	C4—H4A	0.9700
N3—C8	1.362 (3)	C4—H4B	0.9700
N3—H3	0.8600	C5—H5A	0.9700
N4—C9	1.148 (3)	C5—H5B	0.9700
C1—C2	1.520 (3)	C6—C7	1.407 (3)
C1—H1A	0.9700	C7—C9	1.406 (3)
C1—H1B	0.9700	C7—C8	1.442 (3)
C2—C3	1.521 (3)
C6—N1—C1	123.24 (17)	C2—C3—H3B	109.5
C6—N1—C5	122.91 (17)	H3A—C3—H3B	108.1
C1—N1—C5	113.60 (16)	C5—C4—C3	109.84 (19)
C6—N2—N3	108.06 (14)	C5—C4—H4A	109.7
C6—N2—H2	126.0	C3—C4—H4A	109.7
N3—N2—H2	126.0	C5—C4—H4B	109.7
C8—N3—N2	109.28 (15)	C3—C4—H4B	109.7
C8—N3—H3	125.4	H4A—C4—H4B	108.2
N2—N3—H3	125.4	N1—C5—C4	110.09 (17)
N1—C1—C2	109.99 (17)	N1—C5—H5A	109.6
N1—C1—H1A	109.7	C4—C5—H5A	109.6
C2—C1—H1A	109.7	N1—C5—H5B	109.6
N1—C1—H1B	109.7	C4—C5—H5B	109.6
C2—C1—H1B	109.7	H5A—C5—H5B	108.2
H1A—C1—H1B	108.2	N1—C6—N2	120.17 (17)
C1—C2—C3	111.40 (19)	N1—C6—C7	132.01 (18)
C1—C2—H2A	109.3	N2—C6—C7	107.82 (16)
C3—C2—H2A	109.3	C9—C7—C6	131.41 (17)
C1—C2—H2B	109.3	C9—C7—C8	121.20 (17)
C3—C2—H2B	109.3	C6—C7—C8	107.35 (16)
H2A—C2—H2B	108.0	O1—C8—N3	124.15 (18)
C4—C3—C2	110.68 (18)	O1—C8—C7	129.26 (18)
C4—C3—H3A	109.5	N3—C8—C7	106.58 (16)
C2—C3—H3A	109.5	N4—C9—C7	176.5 (2)
C4—C3—H3B	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N4i	0.86	2.32	2.875 (3)	123
N3—H3···O1ii	0.86	2.07	2.772 (2)	138
C4—H4A···O1iii	0.97	2.54	3.258 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N4i	0.86	2.32	2.875 (3)	123
N3—H3⋯O1ii	0.86	2.07	2.772 (2)	138
C4—H4A⋯O1iii	0.97	2.54	3.258 (3)	131

Symmetry codes: (i) ; (ii) ; (iii) .