1-{3-[1-(Hydroxyimino)ethyl]-4-methyl-1H-pyrazol-5-yl}ethanone.

In the title compound, C(8)H(11)N(3)O(2), the oxime and the acetyl groups adopt a transoid conformation, while the pyrazole H atom is localized in the proximity of the acetyl group and is cis with respect to the acetyl O atom. In the crystal, dimers are formed as the result of hydrogen-bonding inter-actions involving the pyrazole NH group of one mol-ecule and the carbonyl O atom of another. The dimers are associated into sheets via O-H⋯N hydrogen bonds involving the oxime hydroxyl and the unprotonated pyrazole N atom, generating a macrocyclic motif with six mol-ecules.

Related literature

For details and applications of related pyrazoles, see: Kovbasyuk et al. (2004 ▶); Krämer & Fritsky (2000 ▶); Sachse et al. (2008 ▶). For the use of azomethine-functionalized pyrazoles in coordination chemistry and catalysis, see: De Geest et al. (2007 ▶); Roy et al. (2008 ▶). For the use of the oxime substituents in the synthesis of polynucleative ligands, see: Kanderal et al. (2005 ▶); Moroz et al. (2010 ▶). For related structures, see: Fritsky et al. (1998 ▶); Mokhir et al. (2002 ▶); Petrusenko et al. (1997 ▶); Sliva et al. (1997 ▶); Świątek-Kozłowska et al. (2000 ▶); Wörl et al. (2005a ▶,b ▶). For the preparation of related ligands, see: Wolff (1902 ▶).

Experimental

Crystal data

C8H11N3O2

M = 181.20

Monoclinic,

a = 9.0721 (2) Å

b = 11.7030 (7) Å

c = 8.2401 (9) Å

β = 104.124 (3)°

V = 848.41 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 120 K

0.46 × 0.33 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.955, T max = 0.987

8532 measured reflections

1925 independent reflections

1486 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.115

wR(F 2) = 0.346

S = 1.12

1925 reflections

125 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.50 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811036518/hy2464sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036518/hy2464Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036518/hy2464Isup3.cml

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

C8H11N3O2	F(000) = 384
Mr = 181.20	Dx = 1.419 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1467 reflections
a = 9.0721 (2) Å	θ = 3.0–27.5°
b = 11.7030 (7) Å	µ = 0.11 mm−1
c = 8.2401 (9) Å	T = 120 K
β = 104.124 (3)°	Block, yellow
V = 848.41 (11) Å3	0.46 × 0.33 × 0.13 mm
Z = 4

Nonius KappaCCD diffractometer	1925 independent reflections
Radiation source: fine-focus sealed tube	1486 reflections with I > 2σ(I)
horizontally mounted graphite crystal	Rint = 0.061
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 2.9°
φ and ω scans with κ offset	h = −11→11
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	k = −14→15
Tmin = 0.955, Tmax = 0.987	l = −10→10
8532 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)] = 0.115	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.346	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.1523P)2 + 2.4348P] where P = (Fo2 + 2Fc2)/3
1925 reflections	(Δ/σ)max = 0.001
125 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

	x	y	z	Uiso*/Ueq
O1	−0.1219 (4)	0.1464 (4)	0.8109 (6)	0.0463 (11)
H1O	−0.1354	0.0584	0.8303	0.069*
O2	0.5690 (4)	0.3709 (3)	0.4582 (5)	0.0401 (10)
N1	0.0051 (5)	0.1629 (3)	0.7433 (6)	0.0307 (10)
N2	0.1958 (4)	0.4074 (3)	0.6374 (5)	0.0293 (9)
N3	0.3189 (4)	0.4064 (3)	0.5780 (5)	0.0280 (9)
H3N	0.3551	0.4681	0.5396	0.034*
C1	0.0281 (5)	0.2679 (4)	0.7208 (6)	0.0272 (10)
C2	−0.0687 (6)	0.3628 (4)	0.7597 (8)	0.0377 (12)
H2A	−0.1725	0.3547	0.6903	0.056*
H2B	−0.0268	0.4364	0.7360	0.056*
H2C	−0.0700	0.3594	0.8781	0.056*
C3	0.1637 (5)	0.2962 (4)	0.6571 (6)	0.0269 (10)
C4	0.2704 (5)	0.2239 (4)	0.6090 (6)	0.0267 (10)
C5	0.2749 (6)	0.0955 (4)	0.6118 (7)	0.0337 (11)
H5A	0.1801	0.0661	0.6327	0.050*
H5B	0.3610	0.0697	0.7009	0.050*
H5C	0.2865	0.0671	0.5037	0.050*
C6	0.3685 (5)	0.2991 (4)	0.5583 (6)	0.0273 (10)
C7	0.5069 (6)	0.2844 (4)	0.4959 (7)	0.0320 (11)
C8	0.5688 (6)	0.1672 (4)	0.4798 (7)	0.0367 (12)
H8A	0.6503	0.1722	0.4210	0.055*
H8B	0.4873	0.1181	0.4165	0.055*
H8C	0.6091	0.1348	0.5915	0.055*

	U11	U22	U33	U12	U13	U23
O1	0.043 (2)	0.042 (2)	0.059 (3)	−0.0029 (16)	0.0225 (19)	0.0047 (19)
O2	0.0369 (19)	0.0322 (19)	0.055 (2)	−0.0066 (15)	0.0191 (17)	0.0020 (17)
N1	0.0314 (19)	0.0256 (19)	0.040 (2)	−0.0020 (15)	0.0179 (16)	−0.0007 (16)
N2	0.035 (2)	0.0204 (19)	0.035 (2)	0.0004 (15)	0.0147 (17)	0.0016 (15)
N3	0.0322 (19)	0.0196 (18)	0.034 (2)	−0.0034 (14)	0.0121 (16)	0.0008 (15)
C1	0.0224 (19)	0.027 (2)	0.032 (2)	0.0001 (16)	0.0058 (17)	0.0007 (18)
C2	0.037 (3)	0.025 (2)	0.055 (3)	0.0029 (19)	0.020 (2)	0.000 (2)
C3	0.032 (2)	0.021 (2)	0.029 (2)	0.0015 (16)	0.0111 (18)	0.0023 (17)
C4	0.028 (2)	0.022 (2)	0.032 (2)	0.0019 (16)	0.0101 (17)	0.0022 (18)
C5	0.042 (3)	0.019 (2)	0.045 (3)	0.0005 (18)	0.021 (2)	0.004 (2)
C6	0.029 (2)	0.021 (2)	0.032 (2)	0.0013 (16)	0.0086 (18)	0.0032 (18)
C7	0.034 (2)	0.027 (2)	0.038 (3)	−0.0040 (18)	0.016 (2)	0.000 (2)
C8	0.031 (2)	0.031 (3)	0.052 (3)	0.0032 (19)	0.018 (2)	0.002 (2)

O1—N1	1.410 (5)	C2—H2C	0.9800
O1—H1O	1.0542	C3—C4	1.413 (6)
O2—C7	1.234 (6)	C4—C6	1.386 (6)
N1—C1	1.267 (6)	C4—C5	1.503 (6)
N2—N3	1.324 (5)	C5—H5A	0.9800
N2—C3	1.353 (6)	C5—H5B	0.9800
N3—C6	1.357 (6)	C5—H5C	0.9800
N3—H3N	0.8839	C6—C7	1.479 (6)
C1—C3	1.487 (6)	C7—C8	1.500 (7)
C1—C2	1.498 (6)	C8—H8A	0.9800
C2—H2A	0.9800	C8—H8B	0.9800
C2—H2B	0.9800	C8—H8C	0.9800
N1—O1—H1O	109.3	C3—C4—C5	127.7 (4)
C1—N1—O1	111.7 (4)	C4—C5—H5A	109.5
N3—N2—C3	105.2 (4)	C4—C5—H5B	109.5
N2—N3—C6	112.8 (4)	H5A—C5—H5B	109.5
N2—N3—H3N	123.1	C4—C5—H5C	109.5
C6—N3—H3N	123.4	H5A—C5—H5C	109.5
N1—C1—C3	116.5 (4)	H5B—C5—H5C	109.5
N1—C1—C2	124.1 (4)	N3—C6—C4	107.2 (4)
C3—C1—C2	119.3 (4)	N3—C6—C7	118.9 (4)
C1—C2—H2A	109.5	C4—C6—C7	133.9 (4)
C1—C2—H2B	109.5	O2—C7—C6	118.1 (4)
H2A—C2—H2B	109.5	O2—C7—C8	121.6 (4)
C1—C2—H2C	109.5	C6—C7—C8	120.3 (4)
H2A—C2—H2C	109.5	C7—C8—H8A	109.5
H2B—C2—H2C	109.5	C7—C8—H8B	109.5
N2—C3—C4	111.1 (4)	H8A—C8—H8B	109.5
N2—C3—C1	118.5 (4)	C7—C8—H8C	109.5
C4—C3—C1	130.4 (4)	H8A—C8—H8C	109.5
C6—C4—C3	103.8 (4)	H8B—C8—H8C	109.5
C6—C4—C5	128.5 (4)
C3—N2—N3—C6	−0.1 (5)	C1—C3—C4—C5	−0.7 (9)
O1—N1—C1—C3	177.3 (4)	N2—N3—C6—C4	−0.1 (6)
O1—N1—C1—C2	−0.6 (7)	N2—N3—C6—C7	−178.9 (4)
N3—N2—C3—C4	0.2 (5)	C3—C4—C6—N3	0.2 (5)
N3—N2—C3—C1	−179.2 (4)	C5—C4—C6—N3	179.9 (5)
N1—C1—C3—N2	−177.5 (4)	C3—C4—C6—C7	178.7 (5)
C2—C1—C3—N2	0.5 (7)	C5—C4—C6—C7	−1.6 (9)
N1—C1—C3—C4	3.2 (8)	N3—C6—C7—O2	−2.6 (8)
C2—C1—C3—C4	−178.8 (5)	C4—C6—C7—O2	179.0 (5)
N2—C3—C4—C6	−0.3 (5)	N3—C6—C7—C8	177.3 (5)
C1—C3—C4—C6	179.0 (5)	C4—C6—C7—C8	−1.0 (9)
N2—C3—C4—C5	−180.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2i	1.05	1.89	2.932 (6)	170
N3—H3N···O2ii	0.88	2.00	2.840 (5)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N2i	1.05	1.89	2.932 (6)	170
N3—H3N⋯O2ii	0.88	2.00	2.840 (5)	157

Symmetry codes: (i) ; (ii) .