2-(3,5-Dimethyl-1H-pyrazol-1-yl)-2-hy­droxy­imino-N′-[1-(pyridin-2-yl)ethyl­idene]acetohydrazide

Plutenko, M.O.; Lampeka, R.D.; Haukka, M.; Nordlander, E.

doi:10.1107/S1600536812045412

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3381

doi:10.1107/S1600536812045412

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2-(3,5-Dimethyl-1H-pyrazol-1-yl)-2-hydroxyimino-N′-[1-(pyridin-2-yl)ethylidene]acetohydrazide

Maxym O. Plutenko,^a ^* Rostislav D. Lampeka,^a Matti Haukka ^b and Ebbe Nordlander ^c

^aDepartment of Chemistry, National Taras Shevchenko University, Volodymyrska Street 64, 01601 Kyiv, Ukraine, ^bDepartment of Chemistry, University of Jyvaskyla, PO Box 35, FI-40014 Jyvaskyla, Finland, and ^cInorganic Chemistry, Center for Chemistry and Chemical Engineering, Lund University, Box 124, SE-221 00 Lund, Sweden
^*Correspondence e-mail: plutenkom@gmail.com

(Received 25 September 2012; accepted 2 November 2012; online 17 November 2012)

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, molecules are connected by N—H⋯O and O—H⋯N hydrogen bonds into supramolecular 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_r = 300.33
Monoclinic, C c
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[F² > 2σ(F²)] = 0.032
wR(F²) = 0.081
S = 1.03
4395 reflections
204 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.36 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
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) $[x, -y+1, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812045412/rz5011sup1.cif

Supporting information file. DOI: 10.1107/S1600536812045412/rz5011Isup2.mol

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

Supporting information file. DOI: 10.1107/S1600536812045412/rz5011Isup4.cml

checkCIF report

Comment top

Polynuclear complexes and supramolecular assemblies based on the bridging ligands are widely used in molecular magnetism, crystal engineering, bioinorganic modeling and catalysis (Świątek-Kozłowska et al., 2000; Wörl et al., 2005). One of the most efficient bridging ligands are oximes. Polydentate ligands containing both oxime and other donor functions (e.g., carboxylic, amide, hydroxamic) are of special interest due to their potential for the bridging mode of coordination and mediation of strong magnetic exchange interactions between metal ions (Sachse et al., 2008) and for the preparation of metal complexes with efficient stabilization of unusually high oxidation states of 3d-metal ions (e.g., copper(III) and nickel(III)) (Kanderal et al., 2005). As a part of our research study we present the structure of the title compound, which comprises several donor groups: oxime, hydrazone, azomethine, and pyridine. It has been shown previously that structurally similiar strand ligands form mono- and tetranuclear grid-like assemblies with 3d-metal ions (Moroz et al., 2012).

In the title compound (Fig. 1), the N—N, N—C and C—O bond lengths of the acetohydrazide group (1.3814 (14), 1.3607 (14) and 1.2204 (14) Å respectively) are typical for the protonated amide group (Kanderal et al., 2005; Sachse et al., 2008; Moroz et al., 2012). The NC(=NOH)C(O)NH fragment deviates from the planarity because of a twist between the oxime and the amide groups about the C(8)—C9 bond; the O(1)—C(8)—C(9)—N(4) torsion angle is 168.65 (11)°. The N—O and C—N bond lengths of the oxime group are 1.370 (1) and 1.281 (0) Å, respectively, that is typical for the amide derivatives of 2-hydroxypropanoic acid (Sliva et al., 1997; Mokhir et al., 2002). The pyridine nitrogen atom is situated in an anti-position with respect to the azomethine group. The C—C, C—N and N—N' (1.3314 (15)–1.4098 (12) Å) bond lengths in the pyrazole ring have typical values. The N4—C9—N5—N6 torsion angle is 63.95 (15)°. The C—N and C—C bond lengths in the pyridine ring are normal for 2-substituted pyridine derivatives (Krämer & Fritsky, 2000; Sachse et al., 2008).

In the crystal packing (Fig. 2), the molecules are connected by N—H···O and O—H···N hydrogen bonds (Table 1) to form chains parallel to the c axis, where the amide nitrogen and the oxime oxygen atoms act as donors and the amide oxygen and the pyrazole nitrogen atoms act as acceptors.

Related literature top

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 top

Synthesis of ethyl 2-[1-(3,5-dimethyl)pyrazolyl]-2-hydroxyiminoacetate: a mixture of ethyl 2-chloro-2-hydroxyiminoacetate synthesized according to Kozikowski et al. (1983) (0.906 g, 6 mmol) and 3,5-dimethylpyrazole (1.152 g, 12 mmol) in 10 ml of chloroform was left for evaporation in the air overnight. The resulting precipitate was recrystallized from water. Yield: 1.12 g (88%).

Synthesis of 2-[1-(3,5-dimethyl)pyrazolyl]-2-hydroxyiminoacetohydrazide: a solution of hydrazine hydrate (0.57 ml, 60%, 10.6 mmol) in water was added to a solution of ethyl 2-[1-(3,5-dimethyl)pyrazolyl]-2-hydroxyiminoacetate (1.12 g, 5.3 mmol) in methanol (30 ml). The resulting mixture was heating under reflux for 1.5 h. After that the solvent was evaporated and the product was recrystallized from methanol. Yield 0.5 g (48%).

Synthesis of 2-[1-(3,5-dimethyl)pyrazolyl]-2-hydroxyimino-N'-[1-(2-pyridyl)ethylidene]acetohydrazide (1): a solution of 2-[1-(3,5-dimethyl)pyrazolyl]-2-hydroxyiminoacetohydrazide (0.5 g, 2.54 mmol) in methanol (30 ml) was treated with 2-acetylpyridine (0.307 g, 2.54 mmol) and the mixture was heated under reflux for 3 h. After that the solvent was evaporated in vacuum and the product was recrystallized from methanol. Yield 0.65 g (85%).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radii.
	Fig. 2. Crystal packing of the title compound. Hydrogen bonds are indicated by dashed lines. H atoms not involved in H-bonds are omitted for clarity.

2-(3,5-Dimethyl-1H-pyrazol-1-yl)-2-hydroxyimino- N'-[1-(pyridin-2-yl)ethylidene]acetohydrazide top

Crystal data top

C₁₄H₁₆N₆O₂	F(000) = 632
M_r = 300.33	D_x = 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

Data collection top

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	R_int = 0.016
Detector resolution: 16 pixels mm^-1	θ_max = 32.2°, θ_min = 1.7°
ϕ scans and ω scans with κ offset	h = −28→36
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	k = −11→11
T_min = 0.966, T_max = 0.980	l = −12→12
8846 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0459P)² + 0.467P] where P = (F_o² + 2F_c²)/3
4395 reflections	(Δ/σ)_max = 0.001
204 parameters	Δρ_max = 0.36 e Å⁻³
3 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₆N₆O₂	V = 1477.32 (6) Å³
M_r = 300.33	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 24.5792 (6) Å	µ = 0.10 mm⁻¹
b = 7.5795 (2) Å	T = 100 K
c = 8.3072 (2) Å	0.36 × 0.28 × 0.21 mm
β = 107.335 (1)°

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	4395 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	4096 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.980	R_int = 0.016
8846 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	3 restraints
wR(F²) = 0.081	H-atom parameters constrained
S = 1.03	Δρ_max = 0.36 e Å⁻³
4395 reflections	Δρ_min = −0.24 e Å⁻³
204 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆N₆O₂
M_r	300.33
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	24.5792 (6), 7.5795 (2), 8.3072 (2)
β (°)	107.335 (1)
V (Å³)	1477.32 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.36 × 0.28 × 0.21

Data collection
Diffractometer	Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.966, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	8846, 4395, 4096
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.751

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.081, 1.03
No. of reflections	4395
No. of parameters	204
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.24

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N6ⁱ	0.88	1.79	2.6686 (13)	175.2
N3—H3N···O1ⁱ	0.86	2.17	3.0196 (13)	174.4

Symmetry code: (i) x, −y+1, z−1/2.

Acknowledgements

Financial support from the State Fund for Fundamental Research of Ukraine (grant No. F40.3/041) and the Swedish Institute (Visby Program) is gratefully acknowledged.

References

Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2010). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kanderal, O. M., Kozłowski, H., Dobosz, A., Świątek-Kozłowska, J., Meyer, F. & Fritsky, I. O. (2005). Dalton Trans. pp. 1428–1437. Web of Science CrossRef PubMed Google Scholar
Kozikowski, A. P. & Adamczyk, M. (1983). J. Org. Chem. 48, 366–372. CrossRef CAS Web of Science Google Scholar
Krämer, R. & Fritsky, I. O. (2000). Eur. J. Org. Chem. pp. 3505–3510. Google Scholar
Mokhir, A. A., Gumienna-Kontecka, E., Swiatek-Kozlowska, J., Petkova, E. G., Fritsky, I. O., Jerzykiewicz, L., Kapshuk, A. A. & Sliva, T. Y. (2002). Inorg. Chim. Acta, 329, 113–121. Web of Science CSD CrossRef CAS Google Scholar
Moroz, Y. S., Demeshko, S., Haukka, M., Mokhir, A., Mitra, U., Stocker, M., Müller, P., Meyer, F. & Fritsky, I. O. (2012). Inorg. Chem. 51, 7445–7447. Web of Science CSD CrossRef CAS PubMed Google Scholar
Sachse, A., Penkova, L., Noel, G., Dechert, S., Varzatskii, O. A., Fritsky, I. O. & Meyer, F. (2008). Synthesis, 5, 800–806. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sliva, T. Yu., Kowalik-Jankowska, T., Amirkhanov, V. M., Głowiak, T., Onindo, C. O., Fritsky, I. O. & Kozłowski, H. (1997). J. Inorg. Biochem. 65, 287–294. CSD CrossRef CAS Web of Science Google Scholar
Świątek-Kozłowska, J., Fritsky, I. O., Dobosz, A., Karaczyn, A., Dudarenko, N. M., Sliva, T. Yu., Gumienna-Kontecka, E. & Jerzykiewicz, L. (2000). J. Chem. Soc. Dalton Trans. pp. 4064–4068. Google Scholar
Wörl, S., Pritzkow, H., Fritsky, I. O. & Krämer, R. (2005). Dalton Trans. pp. 27–29. Google Scholar

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Volume 68| Part 12| December 2012| Page o3381

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-(3,5-Di­methyl-1H-pyrazol-1-yl)-2-hy­dr­oxy­imino-N′-[1-(pyridin-2-yl)ethyl­­idene]acetohydrazide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-(3,5-Dimethyl-1H-pyrazol-1-yl)-2-hydroxyimino-N′-[1-(pyridin-2-yl)ethylidene]acetohydrazide