2-Hydroxy-imino-N'-[1-(2-pyrid-yl)ethyl-idene]propanohydrazide.

The title compound, C(10)H(12)N(4)O(2), features an intra-molecular N-H⋯N hydrogen bond formed between the imine NH and oxime N atoms. The oxime group and the amide C=O bond are anti to each other. In the crystal, mol-ecules are connected by O-H⋯O hydrogen bonds into supra-molecular zigzag chains along the c axis.

Related literature

For oxime and pyridine derivatives, see: Sliva et al. (1997b ▶); Mokhir et al. (2002 ▶); Krämer et al. (2002 ▶); Kovbasyuk et al. (2004 ▶). For 2-hydroxy­imino­propanamide 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 2-hydroxy­imino-N′-[1-(2-pyrid­yl)ethyl­idene]propano­hydra­zone, see: Moroz et al. (2008a ▶,b ▶). For typical bond lengths, see: Bürgi & Dunitz (1994 ▶).

Experimental

Crystal data

C10H12N4O2

M = 220.24

Monoclinic,

a = 4.4498 (11) Å

b = 22.833 (7) Å

c = 10.955 (3) Å

β = 97.47 (2)°

V = 1103.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.15 × 0.10 × 0.05 mm

Data collection

Oxford Diffraction KM-4/Xcalibur diffractometer with a Sapphire3 detector

Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2006 ▶) T min = 0.986, T max = 0.995

3899 measured reflections

958 independent reflections

793 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.097

S = 1.10

958 reflections

155 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data 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/S1600536809033352/tk2523sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033352/tk2523Isup2.hkl

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

C10H12N4O2	F(000) = 464
Mr = 220.24	Dx = 1.325 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5860 reflections
a = 4.4498 (11) Å	θ = 3.6–32.0°
b = 22.833 (7) Å	µ = 0.10 mm−1
c = 10.955 (3) Å	T = 293 K
β = 97.47 (2)°	Needles, white
V = 1103.7 (5) Å3	0.15 × 0.10 × 0.05 mm
Z = 4

Oxford Diffraction KM-4/Xcalibur diffractometer with a Sapphire3 detector	958 independent reflections
Radiation source: Enhance (Mo) X-ray Source	793 reflections with I > 2σ(I)
graphite	Rint = 0.059
Detector resolution: 16.1827 pixels mm-1	θmax = 25.0°, θmin = 3.6°
φ scans and ω scans with κ offset	h = −5→5
Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2006)	k = −25→26
Tmin = 0.986, Tmax = 0.995	l = −12→12
3899 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0453P)2 + 0.2337P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
958 reflections	Δρmax = 0.13 e Å−3
155 parameters	Δρmin = −0.16 e Å−3
2 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

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
N1	−0.4385 (8)	0.29326 (15)	0.1660 (4)	0.0601 (10)
N2	−0.0269 (7)	0.41668 (13)	0.0900 (3)	0.0411 (8)
N3	0.1840 (7)	0.45542 (13)	0.1431 (3)	0.0418 (8)
N4	0.6418 (7)	0.52027 (13)	0.2434 (3)	0.0402 (8)
O1	0.1686 (7)	0.50958 (13)	−0.0301 (3)	0.0624 (9)
O2	0.8544 (6)	0.55993 (14)	0.2979 (3)	0.0559 (8)
C1	−0.3464 (9)	0.33542 (16)	0.0958 (4)	0.0439 (10)
C2	−0.4547 (11)	0.3399 (2)	−0.0272 (4)	0.0624 (13)
H2	−0.3891	0.3701	−0.0743	0.075*
C3	−0.6589 (11)	0.2998 (2)	−0.0793 (5)	0.0763 (16)
H3	−0.7310	0.3019	−0.1628	0.092*
C4	−0.7553 (11)	0.2573 (2)	−0.0090 (5)	0.0706 (15)
H4	−0.8962	0.2296	−0.0423	0.085*
C5	−0.6403 (13)	0.2558 (2)	0.1128 (6)	0.0750 (15)
H5	−0.7085	0.2265	0.1614	0.090*
C6	−0.1176 (8)	0.37676 (17)	0.1582 (3)	0.0425 (10)
C7	−0.0053 (11)	0.3692 (2)	0.2922 (4)	0.0607 (13)
H7A	−0.0416	0.4044	0.3357	0.091*
H7B	0.2082	0.3611	0.3022	0.091*
H7C	−0.1103	0.3372	0.3246	0.091*
C8	0.2702 (8)	0.50043 (16)	0.0783 (3)	0.0405 (9)
C9	0.4981 (9)	0.54051 (15)	0.1430 (3)	0.0404 (10)
C10	0.5493 (13)	0.59805 (19)	0.0889 (5)	0.0755 (16)
H10A	0.3634	0.6119	0.0440	0.113*
H10B	0.7001	0.5945	0.0342	0.113*
H10C	0.6177	0.6253	0.1534	0.113*
H3NA	0.239 (8)	0.4565 (15)	0.222 (4)	0.035 (10)*
H2OA	0.932 (11)	0.5383 (19)	0.355 (5)	0.061 (14)*

	U11	U22	U33	U12	U13	U23
N1	0.063 (2)	0.045 (2)	0.069 (3)	−0.013 (2)	−0.0028 (19)	0.0015 (19)
N2	0.0370 (18)	0.0396 (16)	0.0439 (18)	−0.0042 (15)	−0.0056 (14)	−0.0027 (15)
N3	0.0436 (19)	0.0436 (19)	0.0353 (19)	−0.0083 (16)	−0.0062 (15)	−0.0009 (14)
N4	0.0361 (18)	0.0403 (17)	0.0408 (18)	−0.0022 (15)	−0.0078 (14)	−0.0055 (14)
O1	0.071 (2)	0.0603 (18)	0.0478 (17)	−0.0208 (16)	−0.0238 (15)	0.0105 (14)
O2	0.0555 (18)	0.0570 (18)	0.0478 (17)	−0.0045 (15)	−0.0220 (13)	−0.0013 (14)
C1	0.036 (2)	0.041 (2)	0.054 (2)	0.0004 (18)	0.0032 (19)	−0.0047 (18)
C2	0.068 (3)	0.071 (3)	0.046 (2)	−0.025 (3)	0.002 (2)	−0.007 (2)
C3	0.072 (4)	0.089 (4)	0.063 (3)	−0.026 (3)	−0.007 (3)	−0.020 (3)
C4	0.051 (3)	0.058 (3)	0.100 (4)	−0.020 (2)	0.000 (3)	−0.028 (3)
C5	0.078 (4)	0.052 (3)	0.093 (4)	−0.028 (3)	0.004 (3)	−0.003 (3)
C6	0.045 (3)	0.038 (2)	0.043 (2)	0.0000 (18)	0.0022 (19)	−0.0043 (17)
C7	0.075 (3)	0.061 (3)	0.044 (2)	−0.017 (2)	−0.005 (2)	−0.0039 (19)
C8	0.040 (2)	0.038 (2)	0.039 (2)	0.0029 (18)	−0.0085 (17)	0.0004 (17)
C9	0.047 (3)	0.0368 (19)	0.0342 (19)	0.0021 (18)	−0.0066 (17)	−0.0001 (16)
C10	0.087 (4)	0.059 (3)	0.069 (3)	−0.024 (3)	−0.034 (3)	0.015 (3)

N1—C5	1.320 (6)	C3—C4	1.345 (7)
N1—C1	1.330 (5)	C3—H3	0.9300
N2—C6	1.277 (4)	C4—C5	1.366 (8)
N2—N3	1.364 (4)	C4—H4	0.9300
N3—C8	1.334 (5)	C5—H5	0.9300
N3—H3NA	0.87 (4)	C6—C7	1.498 (5)
N4—C9	1.285 (5)	C7—H7A	0.9600
N4—O2	1.388 (4)	C7—H7B	0.9600
O1—C8	1.233 (4)	C7—H7C	0.9600
O2—H2OA	0.84 (5)	C8—C9	1.477 (5)
C1—C2	1.374 (6)	C9—C10	1.471 (5)
C1—C6	1.488 (5)	C10—H10A	0.9600
C2—C3	1.362 (6)	C10—H10B	0.9600
C2—H2	0.9300	C10—H10C	0.9600
C5—N1—C1	117.2 (4)	N2—C6—C1	115.7 (3)
C6—N2—N3	117.7 (3)	N2—C6—C7	124.4 (4)
C8—N3—N2	120.1 (3)	C1—C6—C7	119.9 (4)
C8—N3—H3NA	116 (2)	C6—C7—H7A	109.5
N2—N3—H3NA	122 (2)	C6—C7—H7B	109.5
C9—N4—O2	111.7 (3)	H7A—C7—H7B	109.5
N4—O2—H2OA	97 (3)	C6—C7—H7C	109.5
N1—C1—C2	121.7 (4)	H7A—C7—H7C	109.5
N1—C1—C6	115.9 (3)	H7B—C7—H7C	109.5
C2—C1—C6	122.4 (4)	O1—C8—N3	123.3 (4)
C3—C2—C1	119.4 (5)	O1—C8—C9	120.0 (3)
C3—C2—H2	120.3	N3—C8—C9	116.7 (3)
C1—C2—H2	120.3	N4—C9—C10	125.5 (4)
C4—C3—C2	119.3 (5)	N4—C9—C8	115.0 (3)
C4—C3—H3	120.3	C10—C9—C8	119.5 (3)
C2—C3—H3	120.3	C9—C10—H10A	109.5
C3—C4—C5	118.1 (4)	C9—C10—H10B	109.5
C3—C4—H4	121.0	H10A—C10—H10B	109.5
C5—C4—H4	121.0	C9—C10—H10C	109.5
N1—C5—C4	124.2 (5)	H10A—C10—H10C	109.5
N1—C5—H5	117.9	H10B—C10—H10C	109.5
C4—C5—H5	117.9
C6—N2—N3—C8	−175.2 (3)	C2—C1—C6—N2	−0.3 (6)
C5—N1—C1—C2	−0.3 (6)	N1—C1—C6—C7	0.2 (5)
C5—N1—C1—C6	−179.7 (4)	C2—C1—C6—C7	−179.2 (4)
N1—C1—C2—C3	−0.9 (7)	N2—N3—C8—O1	−0.1 (6)
C6—C1—C2—C3	178.5 (4)	N2—N3—C8—C9	179.6 (3)
C1—C2—C3—C4	1.3 (8)	O2—N4—C9—C10	0.7 (6)
C2—C3—C4—C5	−0.7 (8)	O2—N4—C9—C8	179.1 (3)
C1—N1—C5—C4	0.9 (8)	O1—C8—C9—N4	−164.0 (4)
C3—C4—C5—N1	−0.5 (9)	N3—C8—C9—N4	16.3 (5)
N3—N2—C6—C1	−179.7 (3)	O1—C8—C9—C10	14.5 (6)
N3—N2—C6—C7	−0.8 (5)	N3—C8—C9—C10	−165.2 (4)
N1—C1—C6—N2	179.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2OA···O1i	0.84 (5)	1.88 (5)	2.709 (4)	170 (5)
N3—H3NA···N4	0.87 (4)	2.30 (4)	2.640 (4)	104 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2OA⋯O1i	0.84 (5)	1.88 (5)	2.709 (4)	170 (5)
N3—H3NA⋯N4	0.87 (4)	2.30 (4)	2.640 (4)	104 (3)

Symmetry code: (i) .