2-(3,5-Dimethyl-1H-pyrazol-1-yl)-2-hy-droxy-imino-N'-[1-(pyridin-2-yl)ethyl-idene]acetohydrazide.

In the title compound, C14H16N6O2, the dihedral angles formed by the mean plane of the acetohydrazide group [maximum deviation 0.0629 (12) Å] with the pyrazole and pyridine rings are 81.62 (6) and 38.38 (4)° respectively. In the crystal, mol-ecules are connected by N-H⋯O and O-H⋯N hydrogen bonds into supra-molecular chains extending parallel to the c-axis direction.

Related literature

For uses of polynuclear complexes, see: Świątek-Kozłowska et al. (2000 ▶); Wörl et al. (2005 ▶). For the use of oximes having additional donor functions as versatile ligands, see: Krämer & Fritsky (2000 ▶); Sachse et al. (2008 ▶); Kanderal et al. (2005 ▶). For related structures, see: Moroz et al. (2012 ▶); Mokhir et al. (2002 ▶); Sliva et al. (1997 ▶). For the synthesis, see: Kozikowski & Adamczyk (1983 ▶).

Experimental

Crystal data

C14H16N6O2

M = 300.33

Monoclinic,

a = 24.5792 (6) Å

b = 7.5795 (2) Å

c = 8.3072 (2) Å

β = 107.335 (1)°

V = 1477.32 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.36 × 0.28 × 0.21 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.966, T max = 0.980

8846 measured reflections

4395 independent reflections

4096 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.081

S = 1.03

4395 reflections

204 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812045412/rz5011sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812045412/rz5011Isup2.mol

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045412/rz5011Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812045412/rz5011Isup4.cml

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

C14H16N6O2	F(000) = 632
Mr = 300.33	Dx = 1.350 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5439 reflections
a = 24.5792 (6) Å	θ = 3.5–32.2°
b = 7.5795 (2) Å	µ = 0.10 mm−1
c = 8.3072 (2) Å	T = 100 K
β = 107.335 (1)°	Block, colourless
V = 1477.32 (6) Å3	0.36 × 0.28 × 0.21 mm
Z = 4

Bruker Kappa APEXII DUO CCD diffractometer	4395 independent reflections
Radiation source: fine-focus sealed tube	4096 reflections with I > 2σ(I)
Curved graphite crystal monochromator	Rint = 0.016
Detector resolution: 16 pixels mm-1	θmax = 32.2°, θmin = 1.7°
φ scans and ω scans with κ offset	h = −28→36
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	k = −11→11
Tmin = 0.966, Tmax = 0.980	l = −12→12
8846 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0459P)2 + 0.467P] where P = (Fo2 + 2Fc2)/3
4395 reflections	(Δ/σ)max = 0.001
204 parameters	Δρmax = 0.36 e Å−3
3 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
O1	0.36481 (4)	0.69023 (11)	0.54259 (10)	0.01537 (16)
O2	0.22703 (4)	0.54704 (12)	0.05549 (11)	0.01825 (18)
H2O	0.2225	0.4597	−0.0165	0.027*
N1	0.56071 (4)	0.19215 (14)	0.65828 (13)	0.01662 (19)
N2	0.42935 (4)	0.41283 (13)	0.53143 (12)	0.01403 (18)
N3	0.38561 (4)	0.46283 (14)	0.39135 (11)	0.01331 (17)
H3N	0.3778	0.4153	0.2937	0.019 (4)*
N4	0.27952 (4)	0.51059 (13)	0.16581 (12)	0.01522 (18)
N5	0.26314 (4)	0.76793 (12)	0.30874 (11)	0.01181 (17)
N6	0.21438 (4)	0.73146 (13)	0.35109 (11)	0.01289 (18)
C1	0.51137 (5)	0.25530 (15)	0.67204 (14)	0.01364 (19)
C2	0.50044 (5)	0.27091 (17)	0.82763 (15)	0.0172 (2)
H2	0.4648	0.3142	0.8333	0.021*
C3	0.54243 (6)	0.22232 (18)	0.97295 (16)	0.0202 (2)
H3	0.5360	0.2318	1.0799	0.024*
C4	0.59418 (5)	0.15935 (17)	0.96004 (15)	0.0185 (2)
H4	0.6240	0.1262	1.0575	0.022*
C5	0.60086 (5)	0.14650 (17)	0.80058 (15)	0.0179 (2)
H5	0.6360	0.1026	0.7916	0.021*
C6	0.46826 (5)	0.30868 (16)	0.51196 (14)	0.01365 (19)
C7	0.47343 (6)	0.24075 (18)	0.34765 (15)	0.0189 (2)
H7A	0.4467	0.1428	0.3084	0.028*
H7B	0.5124	0.1994	0.3634	0.028*
H7C	0.4645	0.3357	0.2638	0.028*
C8	0.35246 (5)	0.59735 (15)	0.41689 (13)	0.01189 (19)
C9	0.29671 (5)	0.62508 (16)	0.28350 (13)	0.01239 (19)
C10	0.19299 (5)	0.88846 (16)	0.37111 (14)	0.0156 (2)
C11	0.13847 (6)	0.89937 (19)	0.41554 (17)	0.0226 (3)
H11A	0.1083	0.9459	0.3192	0.034*
H11B	0.1435	0.9780	0.5126	0.034*
H11C	0.1278	0.7815	0.4440	0.034*
C12	0.22777 (6)	1.02525 (16)	0.34214 (16)	0.0191 (2)
H12	0.2216	1.1485	0.3478	0.023*
C13	0.27257 (5)	0.94425 (15)	0.30399 (15)	0.0156 (2)
C14	0.32359 (6)	1.01682 (18)	0.26595 (17)	0.0227 (3)
H0AA	0.3555	1.0228	0.3700	0.034*
H0AB	0.3151	1.1355	0.2182	0.034*
H0AC	0.3338	0.9401	0.1846	0.034*

	U11	U22	U33	U12	U13	U23
O1	0.0150 (4)	0.0166 (4)	0.0135 (4)	0.0014 (3)	0.0026 (3)	−0.0019 (3)
O2	0.0122 (4)	0.0191 (4)	0.0188 (4)	0.0038 (3)	−0.0025 (3)	−0.0061 (3)
N1	0.0132 (4)	0.0191 (5)	0.0162 (4)	0.0036 (4)	0.0025 (4)	0.0002 (4)
N2	0.0111 (4)	0.0165 (4)	0.0129 (4)	0.0010 (3)	0.0012 (3)	0.0014 (3)
N3	0.0116 (4)	0.0160 (4)	0.0110 (4)	0.0033 (3)	0.0013 (3)	−0.0007 (3)
N4	0.0110 (4)	0.0163 (4)	0.0161 (4)	0.0018 (4)	0.0007 (3)	−0.0024 (4)
N5	0.0111 (4)	0.0104 (4)	0.0139 (4)	0.0001 (3)	0.0036 (3)	−0.0001 (3)
N6	0.0108 (4)	0.0134 (4)	0.0147 (4)	0.0011 (3)	0.0040 (3)	0.0013 (3)
C1	0.0126 (5)	0.0130 (5)	0.0145 (5)	0.0012 (4)	0.0028 (4)	0.0005 (4)
C2	0.0148 (5)	0.0221 (6)	0.0151 (5)	0.0044 (4)	0.0052 (4)	0.0023 (4)
C3	0.0199 (6)	0.0250 (6)	0.0153 (5)	0.0036 (5)	0.0048 (5)	0.0035 (4)
C4	0.0166 (5)	0.0189 (5)	0.0168 (5)	0.0021 (4)	0.0001 (4)	0.0041 (4)
C5	0.0119 (5)	0.0203 (5)	0.0197 (5)	0.0045 (4)	0.0018 (4)	0.0005 (4)
C6	0.0113 (5)	0.0155 (5)	0.0133 (5)	0.0008 (4)	0.0024 (4)	0.0002 (4)
C7	0.0161 (5)	0.0242 (6)	0.0151 (5)	0.0072 (5)	0.0027 (4)	−0.0004 (4)
C8	0.0101 (5)	0.0129 (5)	0.0128 (4)	0.0001 (4)	0.0034 (4)	0.0013 (4)
C9	0.0111 (4)	0.0125 (5)	0.0135 (5)	0.0016 (4)	0.0035 (4)	0.0003 (4)
C10	0.0155 (5)	0.0154 (5)	0.0156 (5)	0.0037 (4)	0.0039 (4)	−0.0009 (4)
C11	0.0183 (6)	0.0264 (6)	0.0249 (6)	0.0057 (5)	0.0094 (5)	−0.0016 (5)
C12	0.0215 (6)	0.0115 (5)	0.0237 (6)	0.0026 (4)	0.0056 (5)	−0.0001 (4)
C13	0.0165 (5)	0.0126 (5)	0.0170 (5)	−0.0014 (4)	0.0039 (4)	0.0018 (4)
C14	0.0208 (6)	0.0207 (6)	0.0277 (6)	−0.0052 (5)	0.0087 (5)	0.0048 (5)

O1—C8	1.2204 (14)	C4—C5	1.3859 (17)
O2—N4	1.3697 (13)	C4—H4	0.9500
O2—H2O	0.8763	C5—H5	0.9500
N1—C1	1.3400 (15)	C6—C7	1.4991 (16)
N1—C5	1.3401 (15)	C7—H7A	0.9800
N2—C6	1.2870 (15)	C7—H7B	0.9800
N2—N3	1.3814 (13)	C7—H7C	0.9800
N3—C8	1.3607 (14)	C8—C9	1.4982 (15)
N3—H3N	0.8555	C10—C12	1.4094 (18)
N4—C9	1.2811 (15)	C10—C11	1.4943 (17)
N5—C13	1.3589 (14)	C11—H11A	0.9800
N5—N6	1.3738 (13)	C11—H11B	0.9800
N5—C9	1.4144 (14)	C11—H11C	0.9800
N6—C10	1.3314 (15)	C12—C13	1.3775 (18)
C1—C2	1.4013 (16)	C12—H12	0.9500
C1—C6	1.4884 (15)	C13—C14	1.4870 (18)
C2—C3	1.3841 (17)	C14—H0AA	0.9800
C2—H2	0.9500	C14—H0AB	0.9800
C3—C4	1.3922 (18)	C14—H0AC	0.9800
C3—H3	0.9500
N4—O2—H2O	102.0	H7A—C7—H7B	109.5
C1—N1—C5	117.66 (10)	C6—C7—H7C	109.5
C6—N2—N3	118.91 (9)	H7A—C7—H7C	109.5
C8—N3—N2	115.22 (9)	H7B—C7—H7C	109.5
C8—N3—H3N	119.2	O1—C8—N3	123.90 (10)
N2—N3—H3N	125.6	O1—C8—C9	119.44 (10)
C9—N4—O2	113.87 (9)	N3—C8—C9	116.61 (9)
C13—N5—N6	112.00 (9)	N4—C9—N5	123.87 (10)
C13—N5—C9	129.53 (10)	N4—C9—C8	119.37 (10)
N6—N5—C9	118.41 (9)	N5—C9—C8	116.30 (9)
C10—N6—N5	105.03 (9)	N6—C10—C12	110.72 (10)
N1—C1—C2	122.41 (11)	N6—C10—C11	119.80 (11)
N1—C1—C6	116.25 (10)	C12—C10—C11	129.47 (11)
C2—C1—C6	121.34 (10)	C10—C11—H11A	109.5
C3—C2—C1	118.94 (11)	C10—C11—H11B	109.5
C3—C2—H2	120.5	H11A—C11—H11B	109.5
C1—C2—H2	120.5	C10—C11—H11C	109.5
C2—C3—C4	119.01 (11)	H11A—C11—H11C	109.5
C2—C3—H3	120.5	H11B—C11—H11C	109.5
C4—C3—H3	120.5	C13—C12—C10	106.18 (10)
C5—C4—C3	117.96 (11)	C13—C12—H12	126.9
C5—C4—H4	121.0	C10—C12—H12	126.9
C3—C4—H4	121.0	N5—C13—C12	106.06 (10)
N1—C5—C4	124.00 (11)	N5—C13—C14	122.13 (11)
N1—C5—H5	118.0	C12—C13—C14	131.80 (11)
C4—C5—H5	118.0	C13—C14—H0AA	109.5
N2—C6—C1	114.35 (9)	C13—C14—H0AB	109.5
N2—C6—C7	126.36 (10)	H0AA—C14—H0AB	109.5
C1—C6—C7	119.29 (10)	C13—C14—H0AC	109.5
C6—C7—H7A	109.5	H0AA—C14—H0AC	109.5
C6—C7—H7B	109.5	H0AB—C14—H0AC	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N6i	0.88	1.79	2.6686 (13)	175
N3—H3N···O1i	0.86	2.17	3.0196 (13)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯N6i	0.88	1.79	2.6686 (13)	175
N3—H3N⋯O1i	0.86	2.17	3.0196 (13)	174

Symmetry code: (i) .