(2E)-2-Hydroxy-imino-N'-[(E)-2-pyridyl-methyl-ene]propanohydrazide.

In the title compound, C(9)H(10)N(4)O(2), the pyridine ring is twisted by 16.5 (1)° from the mean plane defined by the remaining non-H atoms. An intra-molecular N-H⋯N inter-action is present. In the crystal, inter-molecular O-H⋯N and N-H⋯O hydrogen bonds link mol-ecules into layers parallel to the bc plane. The crystal packing exhibits π-π inter-actions indicated by the short distance of 3.649 (1) Å between the centroids of the pyridine rings of neighbouring mol-ecules.

Related literature

For the crystal structures of related oxime derivatives, see: Mokhir et al. (2002 ▶); Moroz et al. (2009 ▶). For 2-hydroxy­imino­propann class="Chemical">amide and amide derivatives of 2-hydroxy­imino­propanoic acid, see: Onindo et al. (1995 ▶); Duda et al. (1997 ▶); Sliva et al. (1997a ▶). For the preparation and characterization of 3d-metal complexes with the structural analog of the title compound, see: Moroz et al. (2008a ▶,b ▶). For the synthesis of 2-(hydroxy­imino)propane­hydrazide, see Fritsky et al. (1998 ▶).

Experimental

Crystal data

C9H10N4O2

M = 206.21

Monoclinic,

a = 10.274 (4) Å

b = 9.717 (4) Å

c = 10.136 (4) Å

β = 109.28 (4)°

V = 955.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.4 × 0.4 × 0.3 mm

Data collection

Kuma KM-4-CCD diffractometer

Absorption correction: none

10648 measured reflections

2680 independent reflections

2449 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.08

2680 reflections

176 parameters

All H-atom parameters refined

Δρmax = 0.46 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data n class="Disease">reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809034400/cv2608sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034400/cv2608Isup2.hkl

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

C9H10N4O2	F(000) = 432
Mr = 206.21	Dx = 1.434 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 11569 reflections
a = 10.274 (4) Å	θ = 3–37°
b = 9.717 (4) Å	µ = 0.11 mm−1
c = 10.136 (4) Å	T = 100 K
β = 109.28 (4)°	Block, white
V = 955.2 (7) Å3	0.4 × 0.4 × 0.3 mm
Z = 4

Kuma KM-4-CCD diffractometer	2449 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.023
graphite	θmax = 30.0°, θmin = 3.2°
Detector resolution: 8.3359 pixels mm-1	h = −14→13
ω scans	k = −13→10
10648 measured reflections	l = −14→14
2680 independent 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	All H-atom parameters refined
S = 1.08	w = 1/[σ2(Fo2) + (0.0621P)2 + 0.2439P] where P = (Fo2 + 2Fc2)/3
2680 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.18 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	0.59592 (7)	0.23238 (7)	0.23853 (7)	0.01751 (17)
O2	0.24735 (8)	0.10483 (8)	−0.16272 (8)	0.01954 (17)
H21	0.2245 (17)	0.1328 (17)	−0.2501 (18)	0.032 (4)*
N1	0.85431 (9)	0.66853 (8)	−0.05564 (8)	0.01561 (18)
N2	0.70574 (8)	0.39826 (8)	0.08234 (8)	0.01477 (17)
N3	0.59208 (9)	0.31588 (9)	0.02612 (9)	0.01608 (18)
H31	0.5529 (16)	0.3104 (16)	−0.0650 (17)	0.030 (4)*
N4	0.36471 (8)	0.18113 (8)	−0.09566 (8)	0.01500 (17)
C1	0.95964 (11)	0.75821 (10)	−0.01987 (11)	0.0176 (2)
H1	0.9570 (16)	0.8267 (16)	−0.0903 (16)	0.029 (4)*
C2	1.06781 (10)	0.75321 (10)	0.10549 (10)	0.0168 (2)
H2	1.1433 (15)	0.8188 (14)	0.1263 (15)	0.023 (3)*
C3	1.06686 (10)	0.64989 (10)	0.20031 (10)	0.0167 (2)
H3	1.1409 (16)	0.6414 (16)	0.2873 (16)	0.026 (4)*
C4	0.95703 (10)	0.55828 (10)	0.16717 (10)	0.01493 (19)
H4	0.9544 (15)	0.4838 (15)	0.2317 (15)	0.024 (3)*
C5	0.85205 (10)	0.57099 (9)	0.03849 (9)	0.01315 (18)
C6	0.73225 (10)	0.47858 (10)	−0.00602 (10)	0.01499 (19)
H6	0.6756 (15)	0.4825 (15)	−0.1032 (15)	0.026 (3)*
C7	0.54344 (10)	0.23721 (9)	0.11115 (10)	0.01334 (18)
C8	0.41629 (10)	0.15545 (9)	0.03573 (10)	0.01366 (19)
C9	0.36358 (11)	0.05663 (11)	0.11943 (11)	0.0188 (2)
H9A	0.2794 (19)	0.0181 (19)	0.0675 (19)	0.044 (5)*
H9B	0.3462 (17)	0.1013 (17)	0.1967 (18)	0.037 (4)*
H9C	0.4325 (17)	−0.0149 (17)	0.1626 (17)	0.035 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0173 (3)	0.0225 (4)	0.0118 (3)	−0.0006 (3)	0.0036 (3)	0.0006 (2)
O2	0.0176 (4)	0.0249 (4)	0.0133 (3)	−0.0076 (3)	0.0014 (3)	−0.0023 (3)
N1	0.0163 (4)	0.0174 (4)	0.0136 (4)	0.0008 (3)	0.0055 (3)	0.0016 (3)
N2	0.0133 (4)	0.0166 (4)	0.0145 (4)	−0.0022 (3)	0.0046 (3)	−0.0024 (3)
N3	0.0160 (4)	0.0202 (4)	0.0109 (4)	−0.0054 (3)	0.0029 (3)	−0.0011 (3)
N4	0.0128 (4)	0.0168 (4)	0.0146 (4)	−0.0022 (3)	0.0036 (3)	−0.0028 (3)
C1	0.0192 (5)	0.0172 (4)	0.0180 (5)	−0.0002 (3)	0.0084 (4)	0.0029 (3)
C2	0.0155 (4)	0.0163 (4)	0.0198 (5)	−0.0018 (3)	0.0076 (4)	−0.0022 (3)
C3	0.0147 (4)	0.0188 (4)	0.0153 (4)	0.0002 (3)	0.0034 (3)	−0.0017 (3)
C4	0.0161 (4)	0.0153 (4)	0.0132 (4)	0.0001 (3)	0.0046 (3)	0.0007 (3)
C5	0.0139 (4)	0.0138 (4)	0.0128 (4)	0.0006 (3)	0.0058 (3)	−0.0011 (3)
C6	0.0147 (4)	0.0171 (4)	0.0126 (4)	−0.0005 (3)	0.0038 (3)	−0.0014 (3)
C7	0.0133 (4)	0.0139 (4)	0.0133 (4)	0.0011 (3)	0.0050 (3)	−0.0004 (3)
C8	0.0136 (4)	0.0139 (4)	0.0139 (4)	0.0001 (3)	0.0051 (3)	−0.0010 (3)
C9	0.0201 (5)	0.0190 (4)	0.0170 (4)	−0.0037 (4)	0.0058 (4)	0.0024 (3)

O1—C7	1.2249 (13)	C2—H2	0.972 (14)
O2—N4	1.3872 (12)	C3—C4	1.3886 (14)
O2—H21	0.881 (17)	C3—H3	0.959 (15)
N1—C1	1.3427 (13)	C4—C5	1.3967 (15)
N1—C5	1.3505 (12)	C4—H4	0.982 (14)
N2—C6	1.2832 (13)	C5—C6	1.4691 (14)
N2—N3	1.3746 (12)	C6—H6	0.965 (14)
N3—C7	1.3643 (12)	C7—C8	1.5042 (14)
N3—H31	0.879 (16)	C8—C9	1.4962 (13)
N4—C8	1.2848 (14)	C9—H9A	0.930 (19)
C1—C2	1.3854 (16)	C9—H9B	0.962 (17)
C1—H1	0.970 (15)	C9—H9C	0.985 (17)
C2—C3	1.3921 (14)
N4—O2—H21	103.1 (11)	N1—C5—C4	122.25 (9)
C1—N1—C5	117.71 (9)	N1—C5—C6	114.84 (9)
C6—N2—N3	114.32 (9)	C4—C5—C6	122.90 (9)
C7—N3—N2	120.18 (8)	N2—C6—C5	120.45 (9)
C7—N3—H31	119.6 (10)	N2—C6—H6	122.7 (9)
N2—N3—H31	120.2 (10)	C5—C6—H6	116.8 (9)
C8—N4—O2	113.47 (8)	O1—C7—N3	124.18 (9)
N1—C1—C2	123.77 (9)	O1—C7—C8	121.44 (9)
N1—C1—H1	115.0 (9)	N3—C7—C8	114.38 (8)
C2—C1—H1	121.2 (9)	N4—C8—C9	127.58 (9)
C1—C2—C3	118.17 (9)	N4—C8—C7	114.58 (9)
C1—C2—H2	121.1 (9)	C9—C8—C7	117.84 (9)
C3—C2—H2	120.7 (9)	C8—C9—H9A	112.3 (11)
C4—C3—C2	119.06 (10)	C8—C9—H9B	111.8 (10)
C4—C3—H3	120.1 (9)	H9A—C9—H9B	104.7 (15)
C2—C3—H3	120.8 (9)	C8—C9—H9C	111.3 (9)
C3—C4—C5	118.98 (9)	H9A—C9—H9C	111.4 (15)
C3—C4—H4	120.7 (8)	H9B—C9—H9C	104.8 (13)
C5—C4—H4	120.3 (8)
C6—N2—N3—C7	−172.56 (9)	N1—C5—C6—N2	−167.65 (9)
C5—N1—C1—C2	2.31 (14)	C4—C5—C6—N2	13.31 (14)
N1—C1—C2—C3	−0.46 (15)	N2—N3—C7—O1	−1.03 (15)
C1—C2—C3—C4	−1.31 (14)	N2—N3—C7—C8	178.35 (8)
C2—C3—C4—C5	1.19 (14)	O2—N4—C8—C9	−0.54 (14)
C1—N1—C5—C4	−2.42 (14)	O2—N4—C8—C7	−179.80 (7)
C1—N1—C5—C6	178.54 (8)	O1—C7—C8—N4	173.25 (9)
C3—C4—C5—N1	0.71 (14)	N3—C7—C8—N4	−6.14 (12)
C3—C4—C5—C6	179.68 (8)	O1—C7—C8—C9	−6.08 (13)
N3—N2—C6—C5	−178.98 (8)	N3—C7—C8—C9	174.52 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H21···N1i	0.881 (17)	1.897 (18)	2.7667 (17)	168.6 (15)
N3—H31···O1ii	0.879 (16)	2.217 (16)	2.9656 (15)	142.9 (14)
N3—H31···N4	0.879 (16)	2.240 (16)	2.6059 (15)	104.7 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H21⋯N1i	0.881 (17)	1.897 (18)	2.7667 (17)	168.6 (15)
N3—H31⋯O1ii	0.879 (16)	2.217 (16)	2.9656 (15)	142.9 (14)
N3—H31⋯N4	0.879 (16)	2.240 (16)	2.6059 (15)	104.7 (12)

Symmetry codes: (i) ; (ii) .