Acetohydrazide.

In the title compound, C(2)H(6)N(2)O, a hydrazine derivative, the asymmetric unit contains two mol-ecules with similar geom-etries. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For general background to hydrazine and its derivatives, see: Gagnon et al. (1951 ▶); Hermanson (1996 ▶); Lumley-Woodyear et al. (1996 ▶); Raddatz et al. (2002 ▶).

Experimental

Crystal data

C2H6N2O

M = 74.09

Monoclinic,

a = 9.5636 (7) Å

b = 8.7642 (6) Å

c = 10.4282 (7) Å

β = 110.886 (1)°

V = 816.63 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART 4K CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.971, T max = 0.990

4189 measured reflections

1762 independent reflections

1604 reflections with I > 2σ(I)

R int = 0.097

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.151

S = 1.15

1762 reflections

112 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809042469/rk2154sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042469/rk2154Isup2.hkl

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

C2H6N2O	F(000) = 320
Mr = 74.09	Dx = 1.205 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2153 reflections
a = 9.5636 (7) Å	θ = 2.5–28.0°
b = 8.7642 (6) Å	µ = 0.10 mm−1
c = 10.4282 (7) Å	T = 298 K
β = 110.886 (1)°	Block, colourless
V = 816.63 (10) Å3	0.20 × 0.15 × 0.10 mm
Z = 8

Bruker SMART 4K CCD diffractometer	1762 independent reflections
Radiation source: fine-focus sealed tube	1604 reflections with I > 2σ(I)
graphite	Rint = 0.097
φ and ω scans	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→12
Tmin = 0.971, Tmax = 0.990	k = −11→9
4189 measured reflections	l = −13→10

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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.151	w = 1/[σ2(Fo2) + (0.061P)2 + 0.1265P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max < 0.001
1762 reflections	Δρmax = 0.19 e Å−3
112 parameters	Δρmin = −0.18 e Å−3
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.17 (2)

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 > 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
C1	0.8855 (2)	0.2274 (2)	0.0022 (2)	0.0608 (5)
H1A	0.9481	0.3141	0.0057	0.091*
H1B	0.7835	0.2603	−0.0227	0.091*
H1C	0.8932	0.1562	−0.0649	0.091*
C2	0.93450 (16)	0.15234 (18)	0.13942 (17)	0.0434 (4)
C3	0.4604 (2)	0.0155 (2)	0.1911 (2)	0.0646 (5)
H3A	0.4598	−0.0526	0.1188	0.097*
H3B	0.3836	−0.0142	0.2254	0.097*
H3C	0.5561	0.0111	0.2640	0.097*
C4	0.43160 (16)	0.17510 (19)	0.13651 (16)	0.0443 (4)
N1	0.83138 (14)	0.13848 (17)	0.19703 (16)	0.0501 (4)
H1D	0.7430 (14)	0.176 (2)	0.1567 (19)	0.060*
N2	0.86280 (16)	0.0740 (2)	0.32791 (17)	0.0575 (5)
H2A	0.9337 (19)	0.128 (2)	0.3837 (19)	0.069*
H2B	0.893 (2)	−0.0180 (14)	0.321 (2)	0.069*
N3	0.30038 (14)	0.23464 (17)	0.12609 (15)	0.0490 (4)
H3D	0.2363 (18)	0.182 (2)	0.148 (2)	0.059*
N4	0.25433 (16)	0.38388 (19)	0.07867 (18)	0.0550 (4)
H4B	0.257 (2)	0.398 (2)	−0.0025 (13)	0.066*
H4A	0.3202 (19)	0.443 (2)	0.1362 (18)	0.066*
O1	1.06315 (12)	0.10511 (15)	0.19701 (13)	0.0578 (4)
O2	0.52482 (11)	0.24591 (14)	0.10257 (13)	0.0560 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0487 (9)	0.0676 (12)	0.0619 (11)	−0.0009 (8)	0.0147 (8)	0.0087 (9)
C2	0.0331 (7)	0.0403 (8)	0.0566 (9)	−0.0026 (6)	0.0158 (6)	−0.0024 (7)
C3	0.0511 (10)	0.0578 (11)	0.0859 (14)	−0.0015 (9)	0.0256 (10)	0.0131 (10)
C4	0.0338 (7)	0.0516 (9)	0.0478 (8)	−0.0028 (6)	0.0149 (6)	−0.0019 (7)
N1	0.0330 (7)	0.0591 (9)	0.0590 (9)	0.0061 (6)	0.0174 (6)	0.0051 (7)
N2	0.0446 (8)	0.0717 (11)	0.0612 (10)	0.0017 (7)	0.0252 (7)	0.0019 (8)
N3	0.0350 (7)	0.0567 (9)	0.0605 (9)	−0.0027 (6)	0.0234 (6)	0.0018 (7)
N4	0.0385 (7)	0.0613 (10)	0.0690 (10)	0.0052 (6)	0.0237 (7)	0.0025 (8)
O1	0.0343 (6)	0.0723 (9)	0.0706 (8)	0.0085 (5)	0.0233 (6)	0.0194 (6)
O2	0.0369 (6)	0.0574 (7)	0.0806 (9)	0.0047 (5)	0.0292 (6)	0.0124 (6)

C1—C2	1.491 (2)	C4—O2	1.2370 (18)
C1—H1A	0.9600	C4—N3	1.327 (2)
C1—H1B	0.9600	N1—N2	1.407 (2)
C1—H1C	0.9600	N1—H1D	0.863 (9)
C2—O1	1.2324 (18)	N2—H2A	0.863 (10)
C2—N1	1.331 (2)	N2—H2B	0.867 (10)
C3—C4	1.498 (3)	N3—N4	1.412 (2)
C3—H3A	0.9600	N3—H3D	0.857 (9)
C3—H3B	0.9600	N4—H4B	0.865 (9)
C3—H3C	0.9600	N4—H4A	0.868 (9)
C2—C1—H1A	109.5	O2—C4—N3	122.42 (16)
C2—C1—H1B	109.5	O2—C4—C3	121.57 (14)
H1A—C1—H1B	109.5	N3—C4—C3	116.01 (14)
C2—C1—H1C	109.5	C2—N1—N2	122.56 (13)
H1A—C1—H1C	109.5	C2—N1—H1D	120.0 (14)
H1B—C1—H1C	109.5	N2—N1—H1D	117.3 (14)
O1—C2—N1	121.40 (16)	N1—N2—H2A	106.0 (15)
O1—C2—C1	122.26 (15)	N1—N2—H2B	104.9 (16)
N1—C2—C1	116.34 (14)	H2A—N2—H2B	111 (2)
C4—C3—H3A	109.5	C4—N3—N4	124.09 (14)
C4—C3—H3B	109.5	C4—N3—H3D	120.8 (14)
H3A—C3—H3B	109.5	N4—N3—H3D	115.1 (14)
C4—C3—H3C	109.5	N3—N4—H4B	110.9 (14)
H3A—C3—H3C	109.5	N3—N4—H4A	104.5 (14)
H3B—C3—H3C	109.5	H4B—N4—H4A	109 (2)
O1—C2—N1—N2	2.0 (3)	O2—C4—N3—N4	−1.3 (3)
C1—C2—N1—N2	−178.17 (16)	C3—C4—N3—N4	179.13 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O2	0.86 (1)	2.05 (1)	2.8971 (17)	166 (2)
N4—H4B···N2i	0.87 (1)	2.34 (1)	3.160 (2)	158 (2)
N4—H4A···O1ii	0.87 (1)	2.22 (1)	3.061 (2)	164 (2)
N3—H3D···O1iii	0.86 (1)	2.02 (1)	2.8599 (17)	167 (2)
N2—H2B···O2iv	0.87 (1)	2.26 (1)	3.065 (2)	155 (2)
N2—H2A···O2v	0.86 (1)	2.40 (2)	3.152 (2)	146 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯O2	0.863 (9)	2.052 (10)	2.8971 (17)	166.0 (19)
N4—H4B⋯N2i	0.865 (9)	2.342 (12)	3.160 (2)	157.9 (19)
N4—H4A⋯O1ii	0.868 (9)	2.216 (11)	3.061 (2)	164.2 (19)
N3—H3D⋯O1iii	0.857 (9)	2.018 (10)	2.8599 (17)	167.1 (19)
N2—H2B⋯O2iv	0.867 (10)	2.255 (13)	3.065 (2)	155 (2)
N2—H2A⋯O2v	0.863 (10)	2.400 (15)	3.152 (2)	145.7 (19)

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