N′-(2-Furylmethyl­ene)acetohydrazide

Abstract

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,

• 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) ų

• 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

• Δρ_max = 0.19 e Å⁻³

• Δρ_min = −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.

Supplementary Material

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

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) .

supplementary crystallographic information

Comment

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).

Experimental

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).

Refinement

H atoms were positioned geometrically (N-H = 0.86 Å and C-H = 0.93 or 0.96Å) and refined using a riding model, with U_iso(H) = 1.2U_eq(C,N) and 1.5U_eq(C_methyl).

Figures

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.

Crystal data

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

Data collection

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

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

Special details

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 (Ų)

	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)

Atomic displacement parameters (Ų)

	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, °)

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, °)

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

Symmetry codes: (i) −x, −y+1, −z+1.