N′-[1-(2-Fur­yl)ethen­yl]propanohydrazide

Guo, H.-M.

doi:10.1107/S1600536807067669

organic compounds

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doi:10.1107/S1600536807067669

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N′-[1-(2-Furyl)ethenyl]propanohydrazide

Huan-Mei Guo ^a ^*

^aDepartment of Chemistry, Weifang College, Weifang 261061, People's Republic of China
^*Correspondence e-mail: huanmeiguo@163.com

(Received 17 June 2007; accepted 19 December 2007; online 23 January 2008)

The title compound, C₉H₁₂N₂O₂, was prepared by the reaction of acetylfuran and propionylhydrazine. The molecule, excluding H atoms, is approximately planar. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature on similar compounds, see: Cimerman et al. (1997 ); Sutherland & Hoy (1968 ); Tucker et al. (1975 ).

Experimental

Crystal data

C₉H₁₂N₂O₂
M_r = 180.21
Triclinic, $[P \overline 1]$
a = 4.3314 (13) Å
b = 9.560 (3) Å
c = 11.695 (4) Å
α = 102.338 (6)°
β = 98.665 (5)°
γ = 91.273 (5)°
V = 466.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 (2) K
0.38 × 0.14 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
2708 measured reflections
1893 independent reflections
1188 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.149
S = 1.01
1893 reflections
120 parameters
H-atom parameters constrained
Δρ_max = 0.23 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—H2⋯O2ⁱ	0.86	2.08	2.925 (2)	166
Symmetry code: (i) -x-1, -y, -z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067669/rt2014sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807067669/rt2014Isup2.hkl

checkCIF report

Comment top

Schiff bases have received considerable attention in the literature, and are attractive from several points of view, such as the possibility of analytical application (Cimerman, et al., 1997). As part of our search for new schiff base compounds, we synthesized the title compound (I). The C7—N2 bond length [1.343 (2) Å] is longer than the typical value for a double bond, but less than for a single bond, due to conjugation effects within the molecule.

Bond lengths and angles in the phenyl ring are normal. The C5—N1 distance of 1.280 (2) Å is similar to the similar distance of 1.287 (2) Å reported in a corresponding compound (Tucker et al., 1975). Similarly, the C7—O2 distance of 1.226 (2) Å is shorter than the similar distance of 1.298 (2) Å reported by Sutherland et al., 1968.

Related literature top

For related literature on similar compounds, see: Cimerman et al. (1997); Sutherland & Hoy (1968); Tucker et al. (1975).

Experimental top

A mixture of the acetyl furan (11 g, 0.10 mol), and propionylhydrazine (8.8 g, 0.10 mol) was stirred in refluxing ethanol (30 ml) for 5 h to afford the title compound (17 g, 0.087 mol, yield 87%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top

Fig. 1. Structure of the title compound at 30% probability displacement ellipsoids showing the atom-numbering scheme.

N'-[1-(2-Furyl)ethenyl]propanohydrazide top

Crystal data top

C₉H₁₂N₂O₂	Z = 2
M_r = 180.21	F(000) = 192
Triclinic, P1	D_x = 1.282 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.3314 (13) Å	Cell parameters from 960 reflections
b = 9.560 (3) Å	θ = 3.8–25.0°
c = 11.695 (4) Å	µ = 0.09 mm⁻¹
α = 102.338 (6)°	T = 294 K
β = 98.665 (5)°	Rod, yellow
γ = 91.273 (5)°	0.38 × 0.14 × 0.14 mm
V = 466.9 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	1188 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.017
Graphite monochromator	θ_max = 26.5°, θ_min = 1.8°
ϕ and ω scans	h = −5→5
2708 measured reflections	k = −11→11
1893 independent reflections	l = −14→11

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0818P)² + 0.0266P] where P = (F_o² + 2F_c²)/3
1893 reflections	(Δ/σ)_max < 0.001
120 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₉H₁₂N₂O₂	γ = 91.273 (5)°
M_r = 180.21	V = 466.9 (3) Å³
Triclinic, P1	Z = 2
a = 4.3314 (13) Å	Mo Kα radiation
b = 9.560 (3) Å	µ = 0.09 mm⁻¹
c = 11.695 (4) Å	T = 294 K
α = 102.338 (6)°	0.38 × 0.14 × 0.14 mm
β = 98.665 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1188 reflections with I > 2σ(I)
2708 measured reflections	R_int = 0.017
1893 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.01	Δρ_max = 0.23 e Å⁻³
1893 reflections	Δρ_min = −0.18 e Å⁻³
120 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	0.5016 (3)	0.10932 (14)	0.42113 (12)	0.0532 (4)
O2	−0.5552 (4)	−0.16062 (16)	0.03731 (13)	0.0648 (5)
N1	0.0408 (3)	0.04514 (17)	0.23834 (13)	0.0438 (4)
N2	−0.1921 (4)	0.00438 (17)	0.14220 (14)	0.0471 (4)
H2	−0.2381	0.0606	0.0945	0.057*
C1	0.7274 (5)	0.1722 (3)	0.51195 (18)	0.0590 (6)
H1	0.8264	0.1264	0.5689	0.071*
C2	0.7882 (5)	0.3074 (3)	0.50874 (19)	0.0616 (6)
H2A	0.9332	0.3725	0.5616	0.074*
C3	0.5891 (5)	0.3330 (2)	0.40919 (18)	0.0542 (6)
H3	0.5778	0.4187	0.3837	0.065*
C4	0.4190 (4)	0.2105 (2)	0.35796 (16)	0.0424 (5)
C5	0.1730 (4)	0.1706 (2)	0.25591 (16)	0.0416 (5)
C6	0.0995 (5)	0.2787 (2)	0.18300 (18)	0.0598 (6)
H6A	0.2015	0.2570	0.1144	0.090*
H6B	0.1721	0.3724	0.2291	0.090*
H6C	−0.1225	0.2766	0.1584	0.090*
C7	−0.3475 (5)	−0.1237 (2)	0.12307 (17)	0.0473 (5)
C8	−0.2606 (5)	−0.2171 (2)	0.20869 (19)	0.0579 (6)
H8A	−0.3313	−0.1758	0.2828	0.070*
H8B	−0.0345	−0.2188	0.2245	0.070*
C9	−0.3969 (7)	−0.3681 (2)	0.1651 (2)	0.0839 (8)
H9A	−0.6207	−0.3674	0.1483	0.126*
H9B	−0.3393	−0.4218	0.2249	0.126*
H9C	−0.3181	−0.4118	0.0942	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0553 (8)	0.0502 (8)	0.0480 (8)	−0.0076 (6)	−0.0124 (7)	0.0125 (7)
O2	0.0681 (10)	0.0591 (9)	0.0549 (9)	−0.0098 (7)	−0.0248 (8)	0.0106 (7)
N1	0.0404 (9)	0.0468 (9)	0.0388 (9)	−0.0009 (7)	−0.0046 (7)	0.0055 (7)
N2	0.0464 (9)	0.0467 (10)	0.0429 (9)	−0.0028 (7)	−0.0096 (7)	0.0103 (7)
C1	0.0565 (13)	0.0668 (15)	0.0453 (12)	−0.0079 (11)	−0.0145 (10)	0.0108 (10)
C2	0.0605 (14)	0.0653 (15)	0.0484 (12)	−0.0172 (11)	−0.0077 (10)	0.0029 (11)
C3	0.0579 (13)	0.0475 (12)	0.0523 (13)	−0.0093 (10)	0.0005 (10)	0.0076 (10)
C4	0.0416 (10)	0.0434 (10)	0.0402 (11)	−0.0023 (8)	0.0027 (9)	0.0078 (8)
C5	0.0393 (10)	0.0442 (11)	0.0403 (11)	0.0007 (8)	0.0054 (8)	0.0082 (8)
C6	0.0613 (14)	0.0611 (13)	0.0548 (14)	−0.0063 (11)	−0.0053 (11)	0.0191 (11)
C7	0.0474 (11)	0.0478 (12)	0.0405 (11)	0.0009 (9)	−0.0069 (9)	0.0056 (9)
C8	0.0639 (13)	0.0508 (12)	0.0528 (13)	−0.0044 (10)	−0.0118 (11)	0.0128 (10)
C9	0.0964 (19)	0.0543 (14)	0.0903 (19)	−0.0127 (13)	−0.0248 (16)	0.0214 (13)

Geometric parameters (Å, º) top

O1—C1	1.354 (2)	C4—C5	1.452 (3)
O1—C4	1.361 (2)	C5—C6	1.485 (3)
O2—C7	1.226 (2)	C6—H6A	0.9600
N1—C5	1.280 (2)	C6—H6B	0.9600
N1—N2	1.374 (2)	C6—H6C	0.9600
N2—C7	1.343 (2)	C7—C8	1.492 (3)
N2—H2	0.8600	C8—C9	1.500 (3)
C1—C2	1.323 (3)	C8—H8A	0.9700
C1—H1	0.9300	C8—H8B	0.9700
C2—C3	1.410 (3)	C9—H9A	0.9600
C2—H2A	0.9300	C9—H9B	0.9600
C3—C4	1.342 (3)	C9—H9C	0.9600
C3—H3	0.9300

C1—O1—C4	106.66 (15)	C5—C6—H6B	109.5
C5—N1—N2	117.46 (16)	H6A—C6—H6B	109.5
C7—N2—N1	119.69 (16)	C5—C6—H6C	109.5
C7—N2—H2	120.2	H6A—C6—H6C	109.5
N1—N2—H2	120.2	H6B—C6—H6C	109.5
C2—C1—O1	110.85 (19)	O2—C7—N2	119.93 (18)
C2—C1—H1	124.6	O2—C7—C8	121.89 (18)
O1—C1—H1	124.6	N2—C7—C8	118.18 (17)
C1—C2—C3	106.23 (19)	C7—C8—C9	113.33 (19)
C1—C2—H2A	126.9	C7—C8—H8A	108.9
C3—C2—H2A	126.9	C9—C8—H8A	108.9
C4—C3—C2	107.3 (2)	C7—C8—H8B	108.9
C4—C3—H3	126.4	C9—C8—H8B	108.9
C2—C3—H3	126.4	H8A—C8—H8B	107.7
C3—C4—O1	109.02 (18)	C8—C9—H9A	109.5
C3—C4—C5	133.29 (19)	C8—C9—H9B	109.5
O1—C4—C5	117.66 (16)	H9A—C9—H9B	109.5
N1—C5—C4	116.21 (17)	C8—C9—H9C	109.5
N1—C5—C6	126.62 (17)	H9A—C9—H9C	109.5
C4—C5—C6	117.16 (16)	H9B—C9—H9C	109.5
C5—C6—H6A	109.5

C5—N1—N2—C7	−177.01 (17)	N2—N1—C5—C6	0.4 (3)
C4—O1—C1—C2	0.3 (2)	C3—C4—C5—N1	−173.8 (2)
O1—C1—C2—C3	−0.2 (3)	O1—C4—C5—N1	4.2 (3)
C1—C2—C3—C4	0.0 (3)	C3—C4—C5—C6	6.0 (3)
C2—C3—C4—O1	0.2 (2)	O1—C4—C5—C6	−176.03 (17)
C2—C3—C4—C5	178.3 (2)	N1—N2—C7—O2	−179.89 (17)
C1—O1—C4—C3	−0.3 (2)	N1—N2—C7—C8	0.4 (3)
C1—O1—C4—C5	−178.77 (16)	O2—C7—C8—C9	12.9 (3)
N2—N1—C5—C4	−179.81 (15)	N2—C7—C8—C9	−167.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	2.08	2.925 (2)	166

Symmetry code: (i) −x−1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₉H₁₂N₂O₂
M_r	180.21
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	4.3314 (13), 9.560 (3), 11.695 (4)
α, β, γ (°)	102.338 (6), 98.665 (5), 91.273 (5)
V (Å³)	466.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.38 × 0.14 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2708, 1893, 1188
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.149, 1.01
No. of reflections	1893
No. of parameters	120
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.86	2.08	2.925 (2)	165.7

Symmetry code: (i) −x−1, −y, −z.

References

Bruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sutherland, H. H. & Hoy, T. G. (1968). Acta Cryst. B24, 1207–1213. CSD CrossRef IUCr Journals Web of Science Google Scholar
Tucker, P. A., Hoekstra, A., ten Cate, J. M. & Vos, A. (1975). Acta Cryst. B31, 733–734. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o508

doi:10.1107/S1600536807067669

Open

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