N'-(Butan-2-yl-idene)furan-2-carbohydrazide.

The title Schiff base compound, C(9)H(12)N(2)O(2), was obtained from a condensation reaction of butan-2-one and furan-2-carbohydrazide. The furan ring and the hydrazide fragment are roughly planar, the largest deviation from the mean plane being 0.069 (2)Å, but the butanyl-idene group is twisted slightly with respect to this plane by a dihedral angle of 5.2 (3)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link pairs of inversion-related mol-ecules, forming dimers of R(2) (2)(8) graph-set motif.

Related literature

For general properties of Schiff bases, see: Kahwa et al. (1986 ▶); Santos et al. (2001 ▶). For related structures containing the n class="Chemical">furan-2-carbohydrazide fragment, see: Jing et al. (2007a ▶,b ▶); Yao & Jing (2007 ▶); Bakir & Gyles (2003 ▶); Tai et al. (2007a ▶,b ▶); Zhou et al. (2007 ▶); Butcher et al. (2007 ▶); Zhao et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

C9H12N2O2

M = 180.21

Monoclinic,

a = 8.2664 (15) Å

b = 16.6687 (13) Å

c = 7.5396 (11) Å

β = 113.171 (19)°

V = 955.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.21 × 0.19 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.978, T max = 0.982

4182 measured reflections

1955 independent reflections

761 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.101

S = 0.74

1955 reflections

120 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038018/dn2605sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038018/dn2605Isup2.hkl

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

C9H12N2O2	F(000) = 384
Mr = 180.21	Dx = 1.253 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1520 reflections
a = 8.2664 (15) Å	θ = 3.1–28.8°
b = 16.6687 (13) Å	µ = 0.09 mm−1
c = 7.5396 (11) Å	T = 293 K
β = 113.171 (19)°	Block, colorless
V = 955.1 (2) Å3	0.21 × 0.19 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1955 independent reflections
Radiation source: fine-focus sealed tube	761 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω scans	θmax = 26.4°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→9
Tmin = 0.978, Tmax = 0.982	k = −18→21
4182 measured reflections	l = −6→9

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 0.74	w = 1/[σ2(Fo2) + (0.0434P)2] where P = (Fo2 + 2Fc2)/3
1955 reflections	(Δ/σ)max = 0.003
120 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.17 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 > 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	0.4993 (2)	0.32297 (8)	0.4042 (2)	0.0598 (5)
O2	0.4694 (2)	0.41298 (8)	0.1056 (2)	0.0670 (6)
N1	0.6592 (3)	0.50672 (9)	0.2784 (3)	0.0511 (6)
H1	0.6497	0.5314	0.1746	0.061*
N2	0.7678 (3)	0.53804 (11)	0.4554 (3)	0.0505 (6)
C1	0.5264 (4)	0.29006 (14)	0.5768 (4)	0.0586 (8)
H1B	0.4800	0.2411	0.5932	0.070*
C2	0.6274 (4)	0.33618 (14)	0.7195 (4)	0.0638 (8)
H2B	0.6641	0.3262	0.8509	0.077*
C3	0.6686 (3)	0.40406 (13)	0.6316 (4)	0.0582 (7)
H3A	0.7383	0.4473	0.6956	0.070*
C4	0.5899 (3)	0.39476 (11)	0.4416 (3)	0.0437 (6)
C5	0.5674 (3)	0.43790 (12)	0.2653 (3)	0.0473 (7)
C6	0.8540 (3)	0.60130 (13)	0.4535 (3)	0.0502 (7)
C7	0.9668 (4)	0.63698 (13)	0.6436 (4)	0.0669 (8)
H7A	0.9302	0.6921	0.6457	0.080*
H7B	1.0872	0.6381	0.6529	0.080*
C8	0.9648 (4)	0.59519 (17)	0.8197 (4)	0.0933 (10)
H8A	1.0343	0.6251	0.9329	0.140*
H8B	1.0128	0.5422	0.8278	0.140*
H8C	0.8459	0.5916	0.8108	0.140*
C9	0.8539 (4)	0.64420 (13)	0.2796 (4)	0.0806 (10)
H9A	0.8447	0.6059	0.1810	0.121*
H9B	0.9613	0.6740	0.3134	0.121*
H9C	0.7557	0.6803	0.2325	0.121*

	U11	U22	U33	U12	U13	U23
O1	0.0962 (15)	0.0377 (8)	0.0454 (11)	−0.0067 (9)	0.0276 (10)	0.0008 (7)
O2	0.1069 (16)	0.0467 (9)	0.0373 (11)	−0.0157 (9)	0.0174 (11)	−0.0023 (8)
N1	0.0748 (15)	0.0400 (10)	0.0386 (12)	−0.0059 (11)	0.0224 (11)	0.0015 (9)
N2	0.0599 (15)	0.0458 (11)	0.0440 (13)	−0.0015 (10)	0.0186 (11)	−0.0015 (9)
C1	0.085 (2)	0.0456 (13)	0.0495 (18)	−0.0007 (14)	0.0312 (16)	0.0107 (12)
C2	0.077 (2)	0.0659 (16)	0.0435 (17)	−0.0090 (15)	0.0182 (16)	0.0110 (13)
C3	0.067 (2)	0.0543 (14)	0.0472 (17)	−0.0152 (13)	0.0155 (15)	0.0028 (12)
C4	0.0572 (18)	0.0318 (12)	0.0431 (15)	0.0011 (11)	0.0208 (13)	0.0017 (10)
C5	0.0661 (19)	0.0369 (13)	0.0406 (16)	0.0038 (13)	0.0228 (15)	−0.0010 (11)
C6	0.0518 (18)	0.0415 (13)	0.0561 (17)	0.0021 (13)	0.0199 (14)	0.0008 (11)
C7	0.060 (2)	0.0655 (16)	0.069 (2)	−0.0095 (14)	0.0184 (17)	−0.0050 (14)
C8	0.092 (3)	0.123 (2)	0.059 (2)	−0.0321 (19)	0.0227 (18)	−0.0138 (18)
C9	0.101 (3)	0.0641 (17)	0.075 (2)	−0.0200 (16)	0.0328 (19)	0.0117 (14)

O1—C1	1.347 (2)	C4—C5	1.457 (3)
O1—C4	1.381 (2)	C6—C7	1.492 (3)
O2—C5	1.229 (2)	C6—C9	1.493 (3)
N1—C5	1.357 (3)	C7—C8	1.505 (3)
N1—N2	1.384 (2)	C7—H7A	0.9700
N1—H1	0.8600	C7—H7B	0.9700
N2—C6	1.276 (3)	C8—H8A	0.9600
C1—C2	1.319 (3)	C8—H8B	0.9600
C1—H1B	0.9300	C8—H8C	0.9600
C2—C3	1.419 (3)	C9—H9A	0.9600
C2—H2B	0.9300	C9—H9B	0.9600
C3—C4	1.329 (3)	C9—H9C	0.9600
C3—H3A	0.9300
C1—O1—C4	106.56 (17)	N2—C6—C9	126.8 (2)
C5—N1—N2	121.40 (19)	C7—C6—C9	115.9 (2)
C5—N1—H1	119.3	C6—C7—C8	116.3 (2)
N2—N1—H1	119.3	C6—C7—H7A	108.2
C6—N2—N1	117.00 (19)	C8—C7—H7A	108.2
C2—C1—O1	111.2 (2)	C6—C7—H7B	108.2
C2—C1—H1B	124.4	C8—C7—H7B	108.2
O1—C1—H1B	124.4	H7A—C7—H7B	107.4
C1—C2—C3	106.0 (2)	C7—C8—H8A	109.5
C1—C2—H2B	127.0	C7—C8—H8B	109.5
C3—C2—H2B	127.0	H8A—C8—H8B	109.5
C4—C3—C2	107.7 (2)	C7—C8—H8C	109.5
C4—C3—H3A	126.1	H8A—C8—H8C	109.5
C2—C3—H3A	126.1	H8B—C8—H8C	109.5
C3—C4—O1	108.49 (19)	C6—C9—H9A	109.5
C3—C4—C5	139.3 (2)	C6—C9—H9B	109.5
O1—C4—C5	112.16 (19)	H9A—C9—H9B	109.5
O2—C5—N1	119.4 (2)	C6—C9—H9C	109.5
O2—C5—C4	121.6 (2)	H9A—C9—H9C	109.5
N1—C5—C4	118.9 (2)	H9B—C9—H9C	109.5
N2—C6—C7	117.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.16	2.981 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.16	2.981 (2)	160

Symmetry code: (i) .