N'-(2-Furylmethyl-ene)acetohydrazide.

In the title mol-ecule, C(7)H(8)N(2)O(2), the acetohydrazide group is planar within 0.014 (2) Å and forms a dihedral angle of 5.35 (8)° with the furan ring. The mol-ecule adopts a trans configuration with respect to the C=N bond. In the crystal, molecules are linked into a chain along the a axis by N-H⋯O hydrogen bonds.

Related literature

For general background to Schiff bases, see: Cimerman et al. (1997 ▶); Offe et al. (1952 ▶); Richardson et al. (1988 ▶). For related structures, see: Li & Jian (2008 ▶); Tamboura et al. (2009 ▶).

Experimental

Crystal data

C7H8N2O2

M = 152.15

Triclinic,

a = 4.4618 (13) Å

b = 9.275 (3) Å

c = 10.541 (4) Å

α = 112.069 (15)°

β = 98.135 (16)°

γ = 101.945 (11)°

V = 383.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 223 K

0.19 × 0.17 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.978, T max = 0.982

2182 measured reflections

1400 independent reflections

918 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.174

S = 0.95

1400 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033571/bg2291sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033571/bg2291Isup2.hkl

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

C7H8N2O2	Z = 2
Mr = 152.15	F(000) = 160
Triclinic, P1	Dx = 1.317 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.4618 (13) Å	Cell parameters from 1400 reflections
b = 9.275 (3) Å	θ = 2.2–25.5°
c = 10.541 (4) Å	µ = 0.10 mm−1
α = 112.069 (15)°	T = 223 K
β = 98.135 (16)°	Block, colourless
γ = 101.945 (11)°	0.19 × 0.17 × 0.16 mm
V = 383.8 (2) Å3

Bruker SMART CCD area-detector diffractometer	1400 independent reflections
Radiation source: fine-focus sealed tube	918 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −5→5
Tmin = 0.978, Tmax = 0.982	k = −11→11
2182 measured reflections	l = −12→12

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.1191P)2] where P = (Fo2 + 2Fc2)/3
1400 reflections	(Δ/σ)max < 0.001
101 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.5605 (4)	0.02737 (18)	0.15111 (17)	0.0701 (6)
O2	−0.0574 (4)	0.58652 (17)	0.37154 (16)	0.0608 (5)
C6	0.0623 (5)	0.4844 (2)	0.3031 (2)	0.0495 (6)
C5	0.4180 (5)	0.2017 (2)	0.3531 (2)	0.0505 (6)
H5	0.4064	0.2313	0.4465	0.061*
C4	0.5534 (5)	0.0730 (3)	0.2899 (2)	0.0518 (6)
C3	0.6756 (6)	−0.0219 (3)	0.3396 (3)	0.0699 (7)
H3	0.6993	−0.0158	0.4307	0.084*
C2	0.7615 (7)	−0.1334 (3)	0.2251 (4)	0.0826 (9)
H2	0.8504	−0.2151	0.2268	0.099*
C7	0.0863 (7)	0.4567 (3)	0.1567 (3)	0.0774 (8)
H7A	0.0404	0.5436	0.1365	0.116*
H7B	−0.0622	0.3557	0.0911	0.116*
H7C	0.2963	0.4531	0.1481	0.116*
C1	0.6908 (7)	−0.0983 (3)	0.1166 (3)	0.0850 (9)
H1	0.7253	−0.1522	0.0282	0.102*
N2	0.1808 (4)	0.39408 (19)	0.36019 (18)	0.0499 (5)
H2A	0.1737	0.4099	0.4454	0.060*
N1	0.3127 (4)	0.27748 (19)	0.28617 (18)	0.0487 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0859 (12)	0.0630 (10)	0.0655 (11)	0.0438 (9)	0.0226 (9)	0.0178 (8)
O2	0.0828 (12)	0.0579 (9)	0.0577 (10)	0.0425 (9)	0.0275 (8)	0.0258 (7)
C6	0.0587 (13)	0.0462 (11)	0.0482 (12)	0.0236 (10)	0.0167 (10)	0.0186 (9)
C5	0.0532 (13)	0.0525 (12)	0.0532 (12)	0.0233 (11)	0.0170 (10)	0.0241 (10)
C4	0.0512 (13)	0.0504 (12)	0.0594 (13)	0.0210 (10)	0.0180 (10)	0.0240 (10)
C3	0.0702 (16)	0.0672 (15)	0.094 (2)	0.0355 (13)	0.0237 (14)	0.0469 (14)
C2	0.0707 (17)	0.0558 (15)	0.130 (3)	0.0367 (13)	0.0245 (17)	0.0383 (17)
C7	0.117 (2)	0.0843 (17)	0.0598 (15)	0.0623 (17)	0.0354 (15)	0.0384 (13)
C1	0.091 (2)	0.0633 (16)	0.091 (2)	0.0469 (16)	0.0227 (16)	0.0084 (14)
N2	0.0627 (12)	0.0505 (10)	0.0475 (10)	0.0313 (9)	0.0216 (9)	0.0214 (8)
N1	0.0533 (11)	0.0457 (10)	0.0530 (11)	0.0244 (8)	0.0182 (8)	0.0195 (8)

O1—C1	1.361 (3)	C3—H3	0.9300
O1—C4	1.369 (3)	C2—C1	1.317 (4)
O2—C6	1.228 (2)	C2—H2	0.9300
C6—N2	1.347 (3)	C7—H7A	0.9600
C6—C7	1.490 (3)	C7—H7B	0.9600
C5—N1	1.276 (3)	C7—H7C	0.9600
C5—C4	1.431 (3)	C1—H1	0.9300
C5—H5	0.9300	N2—N1	1.373 (2)
C4—C3	1.345 (3)	N2—H2A	0.8600
C3—C2	1.425 (4)
C1—O1—C4	106.4 (2)	C3—C2—H2	126.6
O2—C6—N2	120.26 (19)	C6—C7—H7A	109.5
O2—C6—C7	122.07 (19)	C6—C7—H7B	109.5
N2—C6—C7	117.66 (19)	H7A—C7—H7B	109.5
N1—C5—C4	122.5 (2)	C6—C7—H7C	109.5
N1—C5—H5	118.7	H7A—C7—H7C	109.5
C4—C5—H5	118.7	H7B—C7—H7C	109.5
C3—C4—O1	109.4 (2)	C2—C1—O1	111.0 (2)
C3—C4—C5	132.4 (2)	C2—C1—H1	124.5
O1—C4—C5	118.18 (19)	O1—C1—H1	124.5
C4—C3—C2	106.5 (2)	C6—N2—N1	121.83 (18)
C4—C3—H3	126.8	C6—N2—H2A	119.1
C2—C3—H3	126.8	N1—N2—H2A	119.1
C1—C2—C3	106.7 (2)	C5—N1—N2	115.38 (18)
C1—C2—H2	126.6
C1—O1—C4—C3	0.0 (3)	C3—C2—C1—O1	−0.8 (3)
C1—O1—C4—C5	−178.3 (2)	C4—O1—C1—C2	0.5 (3)
N1—C5—C4—C3	−179.8 (2)	O2—C6—N2—N1	179.19 (17)
N1—C5—C4—O1	−1.9 (3)	C7—C6—N2—N1	−1.6 (3)
O1—C4—C3—C2	−0.4 (3)	C4—C5—N1—N2	177.93 (17)
C5—C4—C3—C2	177.6 (2)	C6—N2—N1—C5	179.50 (19)
C4—C3—C2—C1	0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.86	2.06	2.904 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.86	2.06	2.904 (3)	167

Symmetry code: (i) .