N′-(2-Furylmethyl­ene)acetohydrazide

Lv, L.-P.; Yu, T.-M.; Yu, W.-B.; Li, W.-W.; Hu, X.-C.

doi:10.1107/S1600536809033571

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2272

doi:10.1107/S1600536809033571

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N′-(2-Furylmethylene)acetohydrazide

Lu-Ping Lv,^a Tie-Ming Yu,^a Wen-Bo Yu,^a Wei-Wei Li ^a and Xian-Chao Hu ^b ^*

^aDepartment of Chemical Engineering, Hangzhou Vocational and Technical College, Hangzhou 310018, People's Republic of China, and ^bResearch Center of Analysis and Measurement, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: zgdhxc@126.com

(Received 5 August 2009; accepted 23 August 2009; online 29 August 2009)

In the title molecule, C₇H₈N₂O₂, the acetohydrazide group is planar within 0.014 (2) Å and forms a dihedral angle of 5.35 (8)° with the furan ring. The molecule 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_r = 152.15
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.051
wR(F²) = 0.174
S = 0.95
1400 reflections
101 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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

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.

Supporting information

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

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

checkCIF report

Comment top

Schiff bases have attracted much attention due to the possibility of their analytical applications (Cimerman et al., 1997). They are also important ligands, which have been reported to have mild bacteriostatic activity and are used as potential oral iron-chelating drugs for genetic disorders such as thalassemia (Offe et al., 1952; Richardson et al., 1988). Metal complexes based on Schiff bases have received considerable attention because they can be utilized as model compounds of active centres in various complexes (Tamboura et al., 2009). We report here the crystal structure of the title compound (Fig. 1).

The acetohydrazide group is planar and it forms a dihedral angle of 5.35 (8)° with the benzene ring. The molecule adopts a trans configuration with respect to the C═N bond. Bond lengths and angles are comparable to those observed for N'-[1-(4-methoxyphenyl)ethylidene]acetohydrazide (Li et al., 2008).

The molecules are linked into a chain along the a axis by N—H···O hydrogen bonds (Table 1, Fig.2).

Related literature top

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

Experimental top

Furfuraldehyde (0.96 g, 0.01 mol) and acetohydrazide (0.74 g, 0.01 mol) were dissolved in stirred methanol (20 ml) and left for 1.5 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 87% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 485–487 K).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. Part of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

N'-(2-Furylmethylene)acetohydrazide top

Crystal data top

C₇H₈N₂O₂	Z = 2
M_r = 152.15	F(000) = 160
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.1191P)²] where P = (F_o² + 2F_c²)/3
1400 reflections	(Δ/σ)_max < 0.001
101 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₇H₈N₂O₂	γ = 101.945 (11)°
M_r = 152.15	V = 383.8 (2) Å³
Triclinic, P1	Z = 2
a = 4.4618 (13) Å	Mo Kα radiation
b = 9.275 (3) Å	µ = 0.10 mm⁻¹
c = 10.541 (4) Å	T = 223 K
α = 112.069 (15)°	0.19 × 0.17 × 0.16 mm
β = 98.135 (16)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1400 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	918 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.982	R_int = 0.023
2182 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 0.95	Δρ_max = 0.19 e Å⁻³
1400 reflections	Δρ_min = −0.18 e Å⁻³
101 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 > 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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₇H₈N₂O₂
M_r	152.15
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	4.4618 (13), 9.275 (3), 10.541 (4)
α, β, γ (°)	112.069 (15), 98.135 (16), 101.945 (11)
V (Å³)	383.8 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.19 × 0.17 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.978, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	2182, 1400, 918
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.174, 0.95
No. of reflections	1400
No. of parameters	101
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.06	2.904 (3)	167.3

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

The authors thank the Science and Technology Project of Zhejiang Province (grant No. 2007 F70077) and Hangzhou Vocational and Technical College for financial support.

References

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