2-Hydroxy-amino-2-oxoacetohydrazide.

In the title compound, C(2)H(5)N(3)O(3), the hydroxamic group adopts an anti orientation with respect to the hydrazide group. In the crystal, mol-ecules are connected by N-H⋯O and O-H⋯N hydrogen bonds into zigzag chains along the c axis.

Related literature

For hydroxamic acids in biological chemistry, see: Kaczka et al. (1962 ▶); Komatsu et al. (2001 ▶). For the use of hydroxamic acids as strong chelating agents, see: Dobosz et al. (1999 ▶); Świątek-Kozłowska et al. (2000 ▶). For hydroxamic acids as the basis for the synthesis of metallacrowns compounds, see: Bodwin et al. (2001 ▶); Gumienna-Kontecka et al. (2007 ▶). For related structures, see: Sliva et al. (1997a ▶,b ▶); Mokhir et al. (2002 ▶); Fritsky et al. (2006 ▶); Moroz et al. (2008 ▶).

Experimental

Crystal data

C2H5N3O3

M = 119.09

Monoclinic,

a = 9.3968 (7) Å

b = 3.6728 (2) Å

c = 12.7510 (8) Å

β = 95.598 (5)°

V = 437.97 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 77 K

0.12 × 0.10 × 0.07 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.980, T max = 0.988

1149 measured reflections

445 independent reflections

404 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.077

S = 1.06

445 reflections

74 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810012341/jh2142sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012341/jh2142Isup2.hkl

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

C2H5N3O3	F(000) = 248
Mr = 119.09	Dx = 1.806 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1149 reflections
a = 9.3968 (7) Å	θ = 3.2–26.5°
b = 3.6728 (2) Å	µ = 0.17 mm−1
c = 12.7510 (8) Å	T = 77 K
β = 95.598 (5)°	Block, colourless
V = 437.97 (5) Å3	0.12 × 0.10 × 0.07 mm
Z = 4

Bruker APEXII diffractometer	445 independent reflections
Radiation source: fine-focus sealed tube	404 reflections with I > 2σ(I)
horizontally mounted graphite crystal	Rint = 0.021
Detector resolution: 9 pixels mm-1	θmax = 26.5°, θmin = 3.2°
φ scans and ω scans with κ offset	h = −10→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	k = −4→4
Tmin = 0.980, Tmax = 0.988	l = −15→15
1149 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) = 0.077	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0363P)2 + 0.3945P] where P = (Fo2 + 2Fc2)/3
445 reflections	(Δ/σ)max < 0.001
74 parameters	Δρmax = 0.19 e Å−3
3 restraints	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.4570 (5)	0.6710 (10)	0.8492 (3)	0.0187 (10)
C2	0.4385 (4)	0.8528 (9)	0.7408 (3)	0.0149 (9)
N1	0.3439 (4)	0.7171 (8)	0.9018 (3)	0.0185 (8)
H1N1	0.2695	0.8396	0.8732	0.022*
N2	0.5546 (4)	0.8238 (9)	0.6907 (3)	0.0199 (8)
H1N2	0.6295	0.7036	0.7194	0.024*
N3	0.5578 (4)	0.9881 (9)	0.5899 (3)	0.0215 (9)
H1N3	0.6479	1.0696	0.5880	0.032*
H2N3	0.5534	0.8113	0.5371	0.032*
O1	0.3428 (3)	0.5725 (8)	1.0016 (2)	0.0249 (8)
H1O1	0.4139	0.6969	1.0456	0.037*
O2	0.5674 (3)	0.5033 (7)	0.8820 (2)	0.0236 (8)
O3	0.3288 (3)	1.0094 (7)	0.7077 (2)	0.0248 (9)

	U11	U22	U33	U12	U13	U23
C1	0.016 (3)	0.0199 (18)	0.020 (2)	0.0004 (15)	0.0007 (17)	−0.0040 (15)
C2	0.016 (2)	0.0162 (16)	0.013 (2)	0.0003 (14)	0.0037 (17)	−0.0026 (14)
N1	0.0142 (17)	0.0252 (17)	0.0162 (19)	0.0030 (13)	0.0019 (14)	0.0015 (14)
N2	0.0194 (19)	0.0256 (16)	0.015 (2)	0.0059 (14)	0.0050 (14)	0.0019 (14)
N3	0.020 (2)	0.0287 (16)	0.017 (2)	0.0034 (13)	0.0093 (15)	0.0020 (14)
O1	0.0266 (19)	0.0337 (15)	0.0150 (17)	−0.0005 (13)	0.0048 (13)	0.0048 (14)
O2	0.018 (2)	0.0294 (17)	0.024 (2)	0.0081 (12)	0.0057 (16)	0.0060 (12)
O3	0.020 (2)	0.0373 (18)	0.0173 (19)	0.0095 (12)	0.0025 (16)	0.0031 (12)

C1—O2	1.243 (6)	N1—H1N1	0.8800
C1—N1	1.322 (4)	N2—N3	1.422 (6)
C1—C2	1.530 (4)	N2—H1N2	0.8800
C2—O3	1.220 (5)	N3—H1N3	0.9009
C2—N2	1.321 (4)	N3—H2N3	0.9332
N1—O1	1.380 (5)	O1—H1O1	0.9468
O2—C1—N1	125.4 (4)	O1—N1—H1N1	120.1
O2—C1—C2	122.5 (3)	C2—N2—N3	119.6 (4)
N1—C1—C2	112.1 (3)	C2—N2—H1N2	120.2
O3—C2—N2	125.5 (4)	N3—N2—H1N2	120.2
O3—C2—C1	122.4 (3)	N2—N3—H1N3	105.5
N2—C2—C1	112.1 (3)	N2—N3—H2N3	110.6
C1—N1—O1	119.8 (4)	H1N3—N3—H2N3	100.8
C1—N1—H1N1	120.1	N1—O1—H1O1	107.0
O2—C1—C2—O3	178.1 (5)	O2—C1—N1—O1	0.0 (6)
N1—C1—C2—O3	−2.3 (4)	C2—C1—N1—O1	−179.6 (3)
O2—C1—C2—N2	−3.1 (4)	O3—C2—N2—N3	0.8 (6)
N1—C1—C2—N2	176.5 (4)	C1—C2—N2—N3	−178.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O3i	0.88	2.02	2.813 (5)	149
O1—H1O1···N3ii	0.95	1.83	2.740 (4)	161
O1—H1O1···N3ii	0.95	1.83	2.740 (4)	161
N3—H1N3···O1iii	0.90	2.29	3.013 (3)	137
N3—H2N3···O1iv	0.93	2.44	3.024 (4)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O3i	0.88	2.02	2.813 (5)	149
O1—H1O1⋯N3ii	0.95	1.83	2.740 (4)	161
O1—H1O1⋯N3ii	0.95	1.83	2.740 (4)	161
N3—H1N3⋯O1iii	0.90	2.29	3.013 (3)	137
N3—H2N3⋯O1iv	0.93	2.44	3.024 (4)	121

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .