Crystal structure of 2-hy­droxy­imino-2-(pyridin-2-yl)-N′-[1-(pyridin-2-yl)ethyl­idene]acetohydrazide

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

doi:10.1107/S1600536814025793

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Volume 70| Part 12| December 2014| Pages 584-586

doi:10.1107/S1600536814025793

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Crystal structure of 2-hydroxyimino-2-(pyridin-2-yl)-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

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 14 November 2014; accepted 25 November 2014; online 29 November 2014)

The molecule of the title compound, C₁₄H₁₃N₅O₂, is approximately planar (r.m.s deviation for all non-H atoms = 0.093 Å), with the planes of the two pyridine rings inclined to one another by 5.51 (7)°. The oxime group is syn to the amide group, probably due to the formation of an intramolecular N—H⋯N hydrogen bond that forms an S(6) ring motif. In the crystal, molecules are linked by pairs of bifurcated O—H⋯(O,N) hydrogen bonds, forming inversion dimers. The latter are linked via C—H⋯O and C—H⋯N hydrogen bonds, forming sheets lying parallel to (502). The sheets are linked via π–π stacking interactions [inter-centroid distance = 3.7588 (9) Å], involving the pyridine rings of inversion-related molecules, forming a three-dimensional structure.

Keywords: crystal structure; hydroxyimino; acetohydrazide; pyridylethylidene; hydrogen bonding; π–π stacking interactions.

CCDC reference: 1035993

1. Chemical context

Polynuclear oxime-containing ligands have attracted considerable interest because of their ability to act as efficient bridging ligands and for their tendency to form polynuclear metal complexes (Penkova et al., 2010 ; Pavlishchuk et al., 2010 , 2011 ). The presence of additional non-oxime donor functions (e.g. hydrazide, azomethine, pyridine) in the ligand molecule favours the formation of metal complexes with strong magnetic exchange interactions between the metal ions (Pavlishchuk et al., 2011), and complexes which efficiently stabilize unusual high oxidation states of 3d metal ions (Kanderal et al., 2005 ; Fritsky et al., 1998 , 2006 ). As a part of our research study, we present the structure of the title compound, which contains several donor functions of a different nature; oxime, hydrazide, and two different pyridine groups.

2. Structural commentary

The molecular structure of the title compound is illustrated in Fig. 1. The molecule is approximately planar (r.m.s deviation for all non-H atoms = 0.093 Å) with the maximum deviations from the mean plane being 0.255 (1) Å for atom N1, and 0.198 (1) Å for atom O1. The two pyridine rings (N1/C1–C5) and N5/C10–C14) are inclined to one another by 5.51 (7)°. The N2—O1 [1.3691 (14) Å] and C6—N2 [1.2866 (17) Å] bond lengths of the oxime group have typical values (Fritsky et al., 1998). The pyridine N atom, N1, is situated in an anti position with respect to the azomethine group, in accordance with the structures of earlier synthesized ligands of this type (Plutenko et al., 2011 , 2013 ).

Figure 1
A view of the molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular N—H⋯N hydrogen bond is shown as a dashed line (see Table 1

for details).

The N4—N3, N3—C7 and C7—O2 bond lengths of the hydrazide group are 1.3776 (16), 1.3471 (18) and 1.2269 (17) Å, respectively, typical for protonated moieties of this type (Plutenko et al., 2011, 2013). The oxime group is situated in a syn position with respect to the amide group, in contrast to earlier synthesized ligands of this type (Plutenko et al., 2012 , 2013). Such a disposition of these moieties is atypical for amide derivatives of 2-hydroxyiminopropanoic acid (Onindo et al., 1995 ; Sliva et al., 1997 ; Duda et al., 1997 ). It can be explained by the presence of an intramolecular N3—H3⋯N1 hydrogen bond in which the azomethine N atom, N3, acts as donor and the pyridine N atom, N1, acts as an acceptor (Fig. 1 and Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N1	0.89 (2)	1.84 (2)	2.6126 (17)	144 (2)
O1—H1⋯O2ⁱ	0.93 (2)	1.98 (2)	2.8327 (14)	151 (2)
O1—H1⋯N2ⁱ	0.93 (2)	2.13 (2)	2.8489 (16)	133 (2)
C2—H2⋯O2ⁱⁱ	0.95	2.54	3.1985 (15)	127
C3—H3A⋯O1ⁱⁱⁱ	0.95	2.56	3.4755 (15)	163
C13—H13⋯N5^iv	0.95	2.46	3.3811 (19)	163
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x, y-1, z; (iii) -x+1, -y+1, -z; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

3. Supramolecular features

In the crystal, molecules are linked by pairs of bifurcated O—H⋯(O,N) hydrogen bonds forming inversion dimers (Fig. 2 and Table 1). The dimers are linked via C—H⋯O and C—H⋯N hydrogen bonds, forming sheets lying parallel to plane (502). The sheets are linked via π–π stacking interactions, forming a three-dimensional structure [Cg1⋯Cg2ⁱ = 3.7588 (9) Å; Cg1 and Cg2 are the centroids of pyridine rings N1/C1–C5 and N5/C10–C14, respectively; symmetry code: (i) −x + 1, −y + 2, −z + 1].

Figure 2
Crystal packing of the title compound viewed along the b axis. Hydrogen bonds are indicated by dashed lines (see Table 1

for details). H atoms not involved in hydrogen bonds have been omitted for clarity.

4. Database survey

The crystal structures of two very similar compounds have been reported, viz. 2-hydroxyimino-N′-(1-(pyridin-2-yl)ethylidene)propanohydrazide (Moroz et al., 2009 ) and two polymorphs of 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-(hydroxyimino)-N′-(1-(pyridin-2-yl) ethylidene)acetohydrazide (Plutenko et al., 2012, 2013).

5. Synthesis and crystallization

A solution of 2-hydroxyimino-2-(pyridin-2-yl)acetohydrazide (0.36 g, 2 mmol), prepared according to a published procedure (Zyl et al., 1961 ; Kolar et al., 1991 ), in methanol (20 ml) was treated with 2-acetylpyridine (0.242 g, 2 mmol) and the mixture was heated under reflux for 3 h. After cooling, the solvent was evaporated under vacuum and the resulting product was recrystallized from methanol, giving colourless block-like crystals of the title compound (yield 0.52 g; 92%).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The N—H and O—H hydrogen atoms were located in difference Fourier maps and freely refined. The C-bound H atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.95–0.98 Å, and with U_iso = 1.5U_eq(C) for methyl H atoms and = 1.2U_eq(C) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₃N₅O₂
M_r	283.29
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	123
a, b, c (Å)	11.4319 (9), 9.3598 (4), 12.4297 (9)
β (°)	105.016 (3)
V (Å³)	1284.57 (15)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.27 × 0.15 × 0.14

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996 )
T_min, T_max	0.973, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	7900, 2850, 2226
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.115, 1.05
No. of reflections	2850
No. of parameters	196
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.22
Computer programs: APEX2 and SAINT (Bruker, 2010 ), SHELXS97 and SHELXL97 (Sheldrick, 2008 ), DIAMOND (Brandenburg, 2008 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1035993

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814025793/su5024sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814025793/su5024Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814025793/su5024Isup3.mol

Supporting information file. DOI: 10.1107/S1600536814025793/su5024Isup4.cml

checkCIF report

Chemical context top

Polynuclear oxime-containing ligands have attracted considerable interest because of their ability to act as efficient bridging ligands and for their tendency to form polynuclear metal complexes (Penkova et al., 2010; Pavlishchuk et al., 2010, 2011). The presence of additional non-oxime donor functions (e.g. hydrazide, azomethine, pyridine) in the ligand molecule favours the formation of metal complexes with strong magnetic exchange interactions between the metal ions (Pavlishchuk et al., 2011), and complexes which efficiently stabilize unusual high oxidation states of 3d-metal ions (Kanderal et al., 2005; Fritsky et al., 1998, 2006). As a part of our research study, we present the structure of the title compound, which contains several donor functions of a different nature; oxime, hydrazide, and two different pyridine groups.

Structural commentary top

The N4—N3, N3—C7 and C7—O2 bond lengths of the hydrazide group are 1.3776 (16), 1.3471 (18) and 1.2269 (17) Å, respectively, typical for protonated moieties of this type (Plutenko et al., 2011, 2013). The oxime group is situated in a syn position with respect to the amide group, in contrast to earlier synthesized ligands of this type (Plutenko et al., 2012, 2013). Such a disposition of these moieties is atypical for amide derivatives of 2-hydroxyiminopropanoic acid (Onindo et al., 1995; Sliva et al., 1997; Duda et al., 1997). It can be explained by the presence of an intramolecular N3—H3···N1 hydrogen bond in which the azomethine N atom, N3, acts as donor and the pyridine N atom, N1, acts as an acceptor (Fig. 1 and Table 1).

Supramolecular features top

In the crystal, molecules are linked by pairs of bifurcated O—H···(O,N) hydrogen bonds forming inversion dimers (Fig. 2 and Table 1). The dimers are linked via C—H···O and C—H···N hydrogen bonds, forming sheets lying parallel to plane (502). The sheets are linked via π–π stacking interactions, forming a three-dimensional structure [Cg1···Cg2ⁱ = 3.7588 (9) Å; Cg1 and Cg2 are the centroids of pyridine rings N1/C1–C5 and N5/C10–C14, respectively; symmetry code: (i) -x + 1, -y + 2, -z + 1].

Database survey top

The crystal structures of two very similar compounds have been reported, viz. 2-hydroxyimino-N'-(1-(pyridin-2-yl)ethylidene)propanohydrazide (Moroz et al., 2009) and two polymorphs of 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-(hydroxyimino)-N'-(1-(pyridin-2-yl) ethylidene)acetohydrazide (Plutenko et al., 2012, 2013).

Synthesis and crystallization top

A solution of 2-hydroxyimino-2-(pyridin-2-yl)acetohydrazide (0.36 g, 2 mmol), prepared according to a published procedure (Zyl et al., 1961; Kolar et al., 1991), in methanol (20 ml) was treated with 2-acetylpyridine (0.242 g, 2 mmol) and the mixture was heated under reflux for 3 h. After cooling, the solvent was evaporated under vacuum and the resulting product was recrystallized from methanol, giving colourless block-like crystals of the title compound (yield 0.52 g; 92%).

Refinement top

Related literature top

For use of oxime ligands, see: Penkova et al. (2010); Pavlishchuk et al. (2010, 2011). For use of oximes having additional donor functions as versatile ligands, see: Fritsky et al. (1998, 2004, 2006), Kanderal et al. (2005), Onindo et al. (1995); Sliva et al. (1997). For related structures, see: Duda et al. (1997); Kanderal et al. (2005); Sliva et al. (1997); Penkova et al. (2010); Fritsky et al. (2004).

Computing details top

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

Figures top

A view of the molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular N—H···N hydrogen bond is shown as a dashed line (see Table 1 for details).

Crystal packing of the title compound viewed along the b axis. Hydrogen bonds are indicated by dashed lines (see Table 1 for details). H atoms not involved in hydrogen bonds have been omitted for clarity.

2-Hydroxyimino-2-(pyridin-2-yl)-N'-[1-(pyridin-2-yl)ethylidene]acetohydrazide top

Crystal data top

C₁₄H₁₃N₅O₂	F(000) = 592
M_r = 283.29	D_x = 1.465 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 12859 reflections
a = 11.4319 (9) Å	θ = 1.0–27.5°
b = 9.3598 (4) Å	µ = 0.10 mm⁻¹
c = 12.4297 (9) Å	T = 123 K
β = 105.016 (3)°	Block, colourless
V = 1284.57 (15) Å³	0.27 × 0.15 × 0.14 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2850 independent reflections
Radiation source: fine-focus sealed tube	2226 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	R_int = 0.032
Detector resolution: 16 pixels mm^-1	θ_max = 27.6°, θ_min = 3.6°
ϕ scans and ω scans with κ offset	h = −14→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→12
T_min = 0.973, T_max = 0.986	l = −13→16
7900 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0444P)² + 0.5602P] where P = (F_o² + 2F_c²)/3
2850 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₄H₁₃N₅O₂	V = 1284.57 (15) Å³
M_r = 283.29	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.4319 (9) Å	µ = 0.10 mm⁻¹
b = 9.3598 (4) Å	T = 123 K
c = 12.4297 (9) Å	0.27 × 0.15 × 0.14 mm
β = 105.016 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2850 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2226 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.986	R_int = 0.032
7900 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.33 e Å⁻³
2850 reflections	Δρ_min = −0.22 e Å⁻³
196 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	0.53771 (10)	0.81661 (11)	0.01882 (9)	0.0275 (3)
H1	0.547 (2)	0.873 (3)	−0.0406 (19)	0.061 (7)*
O2	0.41325 (12)	1.10609 (11)	0.18548 (9)	0.0365 (3)
N1	0.42020 (13)	0.68309 (13)	0.29508 (10)	0.0269 (3)
N2	0.49655 (12)	0.91005 (12)	0.08547 (10)	0.0227 (3)
N3	0.39671 (12)	0.95674 (13)	0.32531 (10)	0.0217 (3)
H3	0.3983 (18)	0.865 (2)	0.3433 (16)	0.045 (6)*
N4	0.36523 (11)	1.06522 (12)	0.38730 (9)	0.0211 (3)
N5	0.27415 (12)	1.10442 (13)	0.63724 (10)	0.0249 (3)
C1	0.40835 (17)	0.54907 (16)	0.32784 (14)	0.0332 (4)
H1A	0.3841	0.5347	0.3946	0.040*
C2	0.42966 (11)	0.43023 (11)	0.26956 (9)	0.0279 (3)
H2	0.4195	0.3363	0.2946	0.033*
C3	0.46609 (11)	0.45322 (11)	0.17415 (9)	0.0261 (3)
H3A	0.4818	0.3742	0.1320	0.031*
C4	0.48006 (15)	0.59117 (15)	0.13888 (12)	0.0258 (3)
H4	0.5061	0.6074	0.0732	0.031*
C5	0.45529 (13)	0.70606 (14)	0.20141 (11)	0.0196 (3)
C6	0.46209 (13)	0.85875 (14)	0.16827 (11)	0.0198 (3)
C7	0.42130 (14)	0.98666 (14)	0.22744 (12)	0.0225 (3)
C8	0.33284 (13)	1.02516 (14)	0.47426 (11)	0.0206 (3)
C9	0.32455 (16)	0.87266 (15)	0.50997 (13)	0.0282 (4)
H9A	0.2782	0.8166	0.4466	0.042*
H9B	0.2838	0.8694	0.5702	0.042*
H9C	0.4062	0.8327	0.5363	0.042*
C10	0.30190 (13)	1.14279 (14)	0.54298 (11)	0.0200 (3)
C11	0.30120 (14)	1.28513 (15)	0.50943 (12)	0.0253 (3)
H11	0.3217	1.3094	0.4424	0.030*
C12	0.27019 (15)	1.39034 (16)	0.57523 (13)	0.0281 (3)
H12	0.2690	1.4879	0.5539	0.034*
C13	0.24098 (14)	1.35182 (16)	0.67237 (12)	0.0257 (3)
H13	0.2188	1.4216	0.7190	0.031*
C14	0.24502 (15)	1.20881 (16)	0.69948 (12)	0.0275 (3)
H14	0.2259	1.1824	0.7667	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0449 (7)	0.0188 (5)	0.0253 (6)	0.0028 (4)	0.0206 (5)	−0.0006 (4)
O2	0.0691 (9)	0.0166 (5)	0.0338 (6)	0.0044 (5)	0.0315 (6)	0.0034 (4)
N1	0.0415 (8)	0.0172 (6)	0.0263 (6)	0.0000 (5)	0.0165 (6)	−0.0005 (5)
N2	0.0321 (7)	0.0180 (6)	0.0197 (6)	0.0003 (5)	0.0100 (5)	−0.0028 (4)
N3	0.0323 (7)	0.0147 (6)	0.0213 (6)	0.0013 (5)	0.0128 (5)	−0.0003 (4)
N4	0.0278 (7)	0.0173 (6)	0.0203 (6)	0.0010 (5)	0.0102 (5)	−0.0027 (4)
N5	0.0344 (7)	0.0215 (6)	0.0219 (6)	−0.0003 (5)	0.0126 (6)	−0.0005 (5)
C1	0.0550 (11)	0.0207 (7)	0.0314 (8)	−0.0003 (7)	0.0247 (8)	0.0026 (6)
C2	0.0387 (9)	0.0165 (7)	0.0310 (8)	−0.0002 (6)	0.0136 (7)	0.0024 (6)
C3	0.0354 (9)	0.0177 (7)	0.0276 (8)	0.0000 (6)	0.0124 (7)	−0.0035 (5)
C4	0.0372 (9)	0.0196 (7)	0.0242 (7)	−0.0003 (6)	0.0143 (7)	−0.0020 (5)
C5	0.0218 (7)	0.0174 (7)	0.0199 (6)	−0.0007 (5)	0.0062 (5)	−0.0001 (5)
C6	0.0251 (7)	0.0165 (7)	0.0192 (7)	−0.0003 (5)	0.0080 (6)	−0.0008 (5)
C7	0.0315 (8)	0.0164 (7)	0.0218 (7)	−0.0015 (5)	0.0107 (6)	−0.0018 (5)
C8	0.0241 (7)	0.0177 (7)	0.0211 (7)	0.0001 (5)	0.0079 (6)	0.0000 (5)
C9	0.0432 (10)	0.0188 (7)	0.0275 (8)	−0.0003 (6)	0.0177 (7)	0.0015 (5)
C10	0.0229 (7)	0.0188 (7)	0.0190 (7)	−0.0008 (5)	0.0066 (6)	−0.0008 (5)
C11	0.0357 (9)	0.0201 (7)	0.0236 (7)	0.0008 (6)	0.0138 (7)	0.0002 (5)
C12	0.0365 (9)	0.0197 (7)	0.0297 (8)	0.0017 (6)	0.0117 (7)	−0.0011 (6)
C13	0.0289 (8)	0.0237 (7)	0.0257 (7)	0.0024 (6)	0.0090 (6)	−0.0063 (6)
C14	0.0360 (9)	0.0277 (8)	0.0223 (7)	0.0000 (6)	0.0141 (7)	−0.0028 (6)

Geometric parameters (Å, º) top

O1—N2	1.3691 (14)	C4—C5	1.3981 (19)
O1—H1	0.93 (2)	C4—H4	0.9500
O2—C7	1.2269 (17)	C5—C6	1.4950 (18)
N1—C1	1.3365 (19)	C6—C7	1.5392 (18)
N1—C5	1.3435 (18)	C8—C10	1.4911 (18)
N2—C6	1.2866 (17)	C8—C9	1.5051 (19)
N3—C7	1.3471 (18)	C9—H9A	0.9800
N3—N4	1.3776 (16)	C9—H9B	0.9800
N3—H3	0.89 (2)	C9—H9C	0.9800
N4—C8	1.2858 (18)	C10—C11	1.3954 (19)
N5—C10	1.3398 (18)	C11—C12	1.3837 (19)
N5—C14	1.3407 (18)	C11—H11	0.9500
C1—C2	1.3831 (18)	C12—C13	1.382 (2)
C1—H1A	0.9500	C12—H12	0.9500
C2—C3	1.3719	C13—C14	1.378 (2)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.3861 (17)	C14—H14	0.9500
C3—H3A	0.9500

N2—O1—H1	104.1 (14)	O2—C7—C6	120.28 (12)
C1—N1—C5	119.39 (12)	N3—C7—C6	115.45 (11)
C6—N2—O1	118.04 (11)	N4—C8—C10	115.40 (12)
C7—N3—N4	119.85 (12)	N4—C8—C9	125.33 (12)
C7—N3—H3	115.7 (13)	C10—C8—C9	119.27 (12)
N4—N3—H3	124.4 (13)	C8—C9—H9A	109.5
C8—N4—N3	115.41 (12)	C8—C9—H9B	109.5
C10—N5—C14	117.37 (12)	H9A—C9—H9B	109.5
N1—C1—C2	123.35 (13)	C8—C9—H9C	109.5
N1—C1—H1A	118.3	H9A—C9—H9C	109.5
C2—C1—H1A	118.3	H9B—C9—H9C	109.5
C3—C2—C1	117.44 (8)	N5—C10—C11	122.20 (12)
C3—C2—H2	121.3	N5—C10—C8	116.62 (12)
C1—C2—H2	121.3	C11—C10—C8	121.17 (12)
C2—C3—C4	120.34 (7)	C12—C11—C10	119.04 (13)
C2—C3—H3A	119.8	C12—C11—H11	120.5
C4—C3—H3A	119.8	C10—C11—H11	120.5
C3—C4—C5	118.95 (12)	C13—C12—C11	119.20 (14)
C3—C4—H4	120.5	C13—C12—H12	120.4
C5—C4—H4	120.5	C11—C12—H12	120.4
N1—C5—C4	120.51 (12)	C14—C13—C12	117.83 (13)
N1—C5—C6	116.12 (12)	C14—C13—H13	121.1
C4—C5—C6	123.34 (12)	C12—C13—H13	121.1
N2—C6—C5	128.74 (12)	N5—C14—C13	124.36 (14)
N2—C6—C7	106.58 (11)	N5—C14—H14	117.8
C5—C6—C7	124.62 (11)	C13—C14—H14	117.8
O2—C7—N3	124.27 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N1	0.89 (2)	1.84 (2)	2.6126 (17)	144 (2)
O1—H1···O2ⁱ	0.93 (2)	1.98 (2)	2.8327 (14)	151 (2)
O1—H1···N2ⁱ	0.93 (2)	2.13 (2)	2.8489 (16)	133 (2)
C2—H2···O2ⁱⁱ	0.95	2.54	3.1985 (15)	127
C3—H3A···O1ⁱⁱⁱ	0.95	2.56	3.4755 (15)	163
C13—H13···N5^iv	0.95	2.46	3.3811 (19)	163

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x, y−1, z; (iii) −x+1, −y+1, −z; (iv) −x+1/2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N1	0.89 (2)	1.84 (2)	2.6126 (17)	144 (2)
O1—H1···O2ⁱ	0.93 (2)	1.98 (2)	2.8327 (14)	151 (2)
O1—H1···N2ⁱ	0.93 (2)	2.13 (2)	2.8489 (16)	133 (2)
C2—H2···O2ⁱⁱ	0.95	2.54	3.1985 (15)	127
C3—H3A···O1ⁱⁱⁱ	0.95	2.56	3.4755 (15)	163
C13—H13···N5^iv	0.95	2.46	3.3811 (19)	163

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x, y−1, z; (iii) −x+1, −y+1, −z; (iv) −x+1/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃N₅O₂
M_r	283.29
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	123
a, b, c (Å)	11.4319 (9), 9.3598 (4), 12.4297 (9)
β (°)	105.016 (3)
V (Å³)	1284.57 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.27 × 0.15 × 0.14

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.973, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	7900, 2850, 2226
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.115, 1.05
No. of reflections	2850
No. of parameters	196
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.22

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

Acknowledgements

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

References

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Volume 70| Part 12| December 2014| Pages 584-586

doi:10.1107/S1600536814025793

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 2-hy­dr­oxy­imino-2-(pyridin-2-yl)-N′-[1-(pyridin-2-yl)ethyl­­idene]acetohydrazide

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structure of 2-hydroxyimino-2-(pyridin-2-yl)-N′-[1-(pyridin-2-yl)ethylidene]acetohydrazide

3. Supramolecular features