N′-(Butan-2-yl­idene)furan-2-carbohydrazide

Ma, B.; Zhao, Z.; Li, H.

doi:10.1107/S1600536810038018

organic compounds

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Volume 66| Part 10| October 2010| Page o2657

doi:10.1107/S1600536810038018

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N′-(Butan-2-ylidene)furan-2-carbohydrazide

Bu-wei Ma,^a Zhen-xin Zhao ^b ^* and He-ping Li ^c

^aDepartment of Architectural Environment, and Energy Engineering, Henan University of Urban Construction, Pingdingshan 467044, People's Republic of China, ^bDepartment of Chemistry and Chemical Engineering, Henan University of Urban Construction, Pingdingshan 467044, People's Republic of China, and ^cSchool of Chemistry and Biological Engineering, Guilin University of Technology, People's Republic of China
^*Correspondence e-mail: zhao_zhenxin@126.com

(Received 19 September 2010; accepted 23 September 2010; online 30 September 2010)

The title Schiff base compound, C₉H₁₂N₂O₂, 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 butanylidene group is twisted slightly with respect to this plane by a dihedral angle of 5.2 (3)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link pairs of inversion-related molecules, forming dimers of R₂²(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 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_r = 180.21
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.101
S = 0.74
1955 reflections
120 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) -x+1, -y+1, -z.

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.

Supporting information

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

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

checkCIF report

Comment top

The chemistry of Schiff base has attracted a great deal of interest in recent years. These compounds play an important role in the development of various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). In this paper, we synthesized the title compound and reported its crystal structure of the title compound.

The molecular structure of (I) adopts an E conformation with respect to the C=N double bond (Fig.1). The furan ring and the the C5/N1/N2/C6 group are roughly planar with the largest deviation from the mean plane being 0.069 (2)Å but the butan C6/C7/C8/C9 group is slightly twisted with respect to this plane by a dihedral angle of 5.2 (3)°. Distances and bond angles within the furan and the hydrazide moiety agree with related structures found in the literature (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.

Intermolecular N—H···O hydrogen bonds link the molecules two by two around inversion centers to form dimers with a R₂²(8) graph set motif (Etter et al., 1990; Bernstein et al., 1995) (Table 1, Fig. 2).

Related literature top

For general properties of Schiff bases, see: Kahwa et al. (1986); Santos et al. (2001). For related structures containing the 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 top

Furan-2-carbohydrazine (1 mmol, 0.126 g) was dissolved in anhydrous ethanol (10 ml), The mixture was stirred for several minitutes at 351k, butan-2-one(1 mmol, 0.072 g) in ethanol (8 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized from methanol/dicholomethane(1:1), colorless single crystals of (I) was obtained after 3 d.

Computing details top

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

Figures top

	Fig. 1. Molecular view of the title compound with the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small sphere of arbitrary radii.
	Fig. 2. Partial packing view showing the formation of dimer through N-H···O hydogen bonds shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity.

N'-(Butan-2-ylidene)furan-2-carbohydrazide top

Crystal data top

C₉H₁₂N₂O₂	F(000) = 384
M_r = 180.21	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0434P)²] where P = (F_o² + 2F_c²)/3
1955 reflections	(Δ/σ)_max = 0.003
120 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₉H₁₂N₂O₂	V = 955.1 (2) Å³
M_r = 180.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.2664 (15) Å	µ = 0.09 mm⁻¹
b = 16.6687 (13) Å	T = 293 K
c = 7.5396 (11) Å	0.21 × 0.19 × 0.17 mm
β = 113.171 (19)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1955 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	761 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.982	R_int = 0.040
4182 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 0.74	Δρ_max = 0.17 e Å⁻³
1955 reflections	Δρ_min = −0.17 e Å⁻³
120 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₉H₁₂N₂O₂
M_r	180.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.2664 (15), 16.6687 (13), 7.5396 (11)
β (°)	113.171 (19)
V (Å³)	955.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.21 × 0.19 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.978, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	4182, 1955, 761
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.101, 0.74
No. of reflections	1955
No. of parameters	120
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.16	2.981 (2)	160.0

Symmetry code: (i) −x+1, −y+1, −z.

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2657

doi:10.1107/S1600536810038018

Open

access