N′-[4-(2-Fur­yl)but-3-en-2-yl­idene]­iso­nicotino­hydrazide

Yin, Z.-G.; Chen, Y.-Z.; Qian, H.-Y.; Hu, J.

doi:10.1107/S1600536808033242

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2148

doi:10.1107/S1600536808033242

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N′-[4-(2-Furyl)but-3-en-2-ylidene]isonicotinohydrazide

Zhi-Gang Yin,^a ^* Yu-Zhen Chen,^a Heng-Yu Qian ^a and Jie Hu ^a

^aKey Laboratory of Surface and Interface Science of Henan, School of Materials and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: yinck@263.net

(Received 9 October 2008; accepted 13 October 2008; online 22 October 2008)

The molecule of the title Schiff base compound, C₁₄H₁₃N₃O₂, is not perfectly planar; the furyl and pyridine rings are twisted with respect to each other along the C₄N₂C₂ organic chain, making a dihedral angle of 13.3 (1)°. The occurence of N—H⋯O hydrogen bonds builds up a chain developing parallel to the c axis.

Related literature

For background, see: Kahwa et al. (1986 ); Santos et al. (2001 ).

Experimental

Crystal data

C₁₄H₁₃N₃O₂
M_r = 255.27
Monoclinic, P 2₁ /c
a = 16.6325 (14) Å
b = 9.3572 (8) Å
c = 8.3554 (7) Å
β = 100.912 (1)°
V = 1276.87 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.25 × 0.23 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.965, T_max = 0.978
11728 measured reflections
3151 independent reflections
2124 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.132
S = 1.03
3151 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 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	2.26	2.9289 (16)	134
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033242/dn2389sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033242/dn2389Isup2.hkl

checkCIF report

Comment top

The chemistry of Schiff bases 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). As part of our interest in the study of the coordination chemistry of Schiff bases, we have synthesized the title compound (I) and reported its cyrstal structure.

The molecule of the title compound is not perfectly planar, the furyl and the pyridine rings are twisted to each other along the C5/C6/C7/C8/N1/N2/C9 organic chain making a dihedral angle of 13.3 (1)°(Fig. 1). The organic chain is nearly planar with the largest deviation from the mean plane being 0.039 (1)Å at C7. The occurence of N-H···O hydrogen bonds builts up a chain developing parallel to the c axis (Fig. 2, Table 1).

Related literature top

For background, see: Kahwa et al. (1986); Santos et al. (2001).

Experimental top

Pyridine-4-carboxylic acid hydrazide (1 mmol, 0.137 g) was dissolved in anhydrous methanol, H₂SO₄ (98% 0.5 ml) was added to this, the mixture was stirred for several minitutes at 351 K, furylideneacetone (1 mmol 0.136 g) in methanol (8 ml) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized in dichloromethane, brown single crystals of (I) was obtained after 5 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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular view of (I) with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view showing the N-H···O hydrogen bondings resulting in the formation of a chain parallel to the c axis. H atoms not involved in hydrogen bondings have been omitted for clarity. H bonds are shown as dashed lines. [Symmetry code: (i) x, -y+3/2, z+1/2]

N'-[4-(2-Furyl)but-3-en-2-ylidene]isonicotinohydrazide top

Crystal data top

C₁₄H₁₃N₃O₂	F(000) = 536
M_r = 255.27	D_x = 1.328 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2552 reflections
a = 16.6325 (14) Å	θ = 2.2–24.8°
b = 9.3572 (8) Å	µ = 0.09 mm⁻¹
c = 8.3554 (7) Å	T = 293 K
β = 100.912 (1)°	Block, brown
V = 1276.87 (19) Å³	0.25 × 0.23 × 0.16 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3151 independent reflections
Radiation source: fine-focus sealed tube	2124 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 28.3°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −22→20
T_min = 0.965, T_max = 0.978	k = −12→12
11728 measured reflections	l = −11→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) = 0.132	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0611P)² + 0.1613P] where P = (F_o² + 2F_c²)/3
3151 reflections	(Δ/σ)_max = 0.005
173 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₄H₁₃N₃O₂	V = 1276.87 (19) Å³
M_r = 255.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.6325 (14) Å	µ = 0.09 mm⁻¹
b = 9.3572 (8) Å	T = 293 K
c = 8.3554 (7) Å	0.25 × 0.23 × 0.16 mm
β = 100.912 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3151 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2124 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.978	R_int = 0.026
11728 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
3151 reflections	Δρ_min = −0.22 e Å⁻³
173 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
C1	−0.34240 (10)	0.8729 (3)	0.0347 (2)	0.0765 (6)
H1	−0.3937	0.9084	0.0428	0.092*
C2	−0.33013 (10)	0.7542 (2)	−0.0421 (2)	0.0679 (5)
H2	−0.3700	0.6929	−0.0970	0.081*
C3	−0.24415 (10)	0.73836 (19)	−0.0245 (2)	0.0606 (4)
H3	−0.2168	0.6641	−0.0654	0.073*
C4	−0.20947 (9)	0.85094 (17)	0.06234 (19)	0.0510 (4)
C5	−0.12679 (9)	0.89496 (16)	0.12619 (19)	0.0496 (4)
H5	−0.1190	0.9739	0.1949	0.060*
C6	−0.06062 (8)	0.82982 (14)	0.09315 (18)	0.0454 (3)
H6	−0.0694	0.7556	0.0178	0.055*
C7	0.02404 (8)	0.86343 (14)	0.16352 (17)	0.0424 (3)
C8	0.04425 (9)	0.98435 (16)	0.2800 (2)	0.0547 (4)
H8A	0.0616	0.9475	0.3883	0.082*
H8B	−0.0033	1.0432	0.2765	0.082*
H8C	0.0875	1.0403	0.2503	0.082*
C9	0.21798 (8)	0.73017 (15)	0.13795 (17)	0.0439 (3)
C10	0.30344 (8)	0.77406 (15)	0.21280 (17)	0.0450 (3)
C11	0.32441 (9)	0.90777 (17)	0.2786 (2)	0.0540 (4)
H11	0.2842	0.9759	0.2829	0.065*
C12	0.40575 (10)	0.93870 (19)	0.3378 (2)	0.0653 (5)
H12	0.4186	1.0289	0.3821	0.078*
C13	0.44536 (11)	0.7198 (2)	0.2728 (3)	0.0838 (6)
H13	0.4868	0.6536	0.2703	0.101*
C14	0.36583 (10)	0.67795 (19)	0.2110 (2)	0.0651 (5)
H14	0.3547	0.5865	0.1689	0.078*
N1	0.07718 (7)	0.77927 (12)	0.11825 (15)	0.0466 (3)
N2	0.15805 (7)	0.80590 (12)	0.18733 (15)	0.0475 (3)
H2A	0.1701	0.8704	0.2613	0.057*
N3	0.46678 (9)	0.84786 (19)	0.3355 (2)	0.0772 (5)
O1	−0.26987 (7)	0.93681 (14)	0.10076 (15)	0.0705 (4)
O2	0.20525 (6)	0.63417 (12)	0.03656 (13)	0.0573 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0337 (9)	0.1172 (16)	0.0746 (13)	0.0063 (9)	0.0004 (8)	−0.0027 (12)
C2	0.0450 (10)	0.0840 (12)	0.0703 (12)	−0.0101 (9)	−0.0003 (8)	0.0038 (10)
C3	0.0477 (9)	0.0634 (9)	0.0681 (11)	−0.0004 (7)	0.0043 (8)	−0.0046 (8)
C4	0.0366 (8)	0.0627 (9)	0.0519 (9)	0.0068 (6)	0.0039 (6)	0.0025 (7)
C5	0.0401 (8)	0.0524 (8)	0.0533 (9)	0.0031 (6)	0.0012 (6)	−0.0001 (7)
C6	0.0390 (8)	0.0452 (7)	0.0489 (8)	0.0002 (6)	0.0002 (6)	0.0010 (6)
C7	0.0375 (7)	0.0415 (7)	0.0463 (8)	0.0010 (5)	0.0033 (6)	0.0039 (6)
C8	0.0425 (8)	0.0518 (8)	0.0649 (10)	0.0036 (6)	−0.0024 (7)	−0.0087 (7)
C9	0.0383 (7)	0.0502 (7)	0.0421 (8)	0.0003 (6)	0.0045 (6)	0.0005 (6)
C10	0.0357 (7)	0.0553 (8)	0.0434 (8)	−0.0004 (6)	0.0059 (6)	0.0005 (6)
C11	0.0382 (8)	0.0560 (9)	0.0693 (10)	−0.0045 (6)	0.0138 (7)	−0.0041 (8)
C12	0.0436 (9)	0.0708 (10)	0.0827 (12)	−0.0121 (8)	0.0147 (8)	−0.0144 (9)
C13	0.0405 (10)	0.0959 (14)	0.1109 (17)	0.0142 (9)	0.0039 (10)	−0.0275 (13)
C14	0.0449 (9)	0.0705 (10)	0.0769 (12)	0.0066 (8)	0.0039 (8)	−0.0174 (9)
N1	0.0329 (6)	0.0516 (6)	0.0526 (7)	−0.0027 (5)	0.0010 (5)	−0.0038 (5)
N2	0.0332 (6)	0.0528 (7)	0.0540 (7)	−0.0018 (5)	0.0021 (5)	−0.0111 (6)
N3	0.0382 (8)	0.0978 (12)	0.0931 (12)	−0.0041 (7)	0.0058 (7)	−0.0236 (9)
O1	0.0407 (6)	0.0913 (9)	0.0753 (8)	0.0138 (6)	0.0007 (5)	−0.0177 (7)
O2	0.0467 (6)	0.0676 (7)	0.0548 (7)	0.0016 (5)	0.0025 (5)	−0.0162 (5)

Geometric parameters (Å, º) top

C1—C2	1.317 (3)	C8—H8C	0.9600
C1—O1	1.366 (2)	C9—O2	1.2253 (17)
C1—H1	0.9300	C9—N2	1.3496 (18)
C2—C3	1.417 (2)	C9—C10	1.4980 (19)
C2—H2	0.9300	C10—C14	1.375 (2)
C3—C4	1.346 (2)	C10—C11	1.385 (2)
C3—H3	0.9300	C11—C12	1.380 (2)
C4—O1	1.3711 (18)	C11—H11	0.9300
C4—C5	1.438 (2)	C12—N3	1.327 (2)
C5—C6	1.332 (2)	C12—H12	0.9300
C5—H5	0.9300	C13—N3	1.330 (2)
C6—C7	1.4540 (19)	C13—C14	1.382 (2)
C6—H6	0.9300	C13—H13	0.9300
C7—N1	1.2926 (18)	C14—H14	0.9300
C7—C8	1.489 (2)	N1—N2	1.3822 (15)
C8—H8A	0.9600	N2—H2A	0.8600
C8—H8B	0.9600

C2—C1—O1	111.08 (16)	H8B—C8—H8C	109.5
C2—C1—H1	124.5	O2—C9—N2	123.73 (13)
O1—C1—H1	124.5	O2—C9—C10	121.05 (13)
C1—C2—C3	106.49 (16)	N2—C9—C10	115.20 (12)
C1—C2—H2	126.8	C14—C10—C11	117.48 (14)
C3—C2—H2	126.8	C14—C10—C9	118.32 (14)
C4—C3—C2	107.16 (16)	C11—C10—C9	124.15 (13)
C4—C3—H3	126.4	C12—C11—C10	119.20 (15)
C2—C3—H3	126.4	C12—C11—H11	120.4
C3—C4—O1	109.08 (13)	C10—C11—H11	120.4
C3—C4—C5	134.95 (15)	N3—C12—C11	124.13 (16)
O1—C4—C5	115.91 (13)	N3—C12—H12	117.9
C6—C5—C4	124.18 (14)	C11—C12—H12	117.9
C6—C5—H5	117.9	N3—C13—C14	124.65 (17)
C4—C5—H5	117.9	N3—C13—H13	117.7
C5—C6—C7	126.31 (14)	C14—C13—H13	117.7
C5—C6—H6	116.8	C10—C14—C13	118.77 (16)
C7—C6—H6	116.8	C10—C14—H14	120.6
N1—C7—C6	114.42 (12)	C13—C14—H14	120.6
N1—C7—C8	124.89 (12)	C7—N1—N2	115.67 (11)
C6—C7—C8	120.68 (12)	C9—N2—N1	119.63 (12)
C7—C8—H8A	109.5	C9—N2—H2A	120.2
C7—C8—H8B	109.5	N1—N2—H2A	120.2
H8A—C8—H8B	109.5	C12—N3—C13	115.76 (15)
C7—C8—H8C	109.5	C1—O1—C4	106.18 (14)
H8A—C8—H8C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.26	2.9289 (16)	134

Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃N₃O₂
M_r	255.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	16.6325 (14), 9.3572 (8), 8.3554 (7)
β (°)	100.912 (1)
V (Å³)	1276.87 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.23 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.965, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	11728, 3151, 2124
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.132, 1.03
No. of reflections	3151
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.22

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.26	2.9289 (16)	134.2

Symmetry code: (i) x, −y+3/2, z+1/2.

Acknowledgements

The authors express their deep appreciation to the Outstanding Youth Fund for Henan Natural Scientific Research (grant No. 0512001100) and the Fund for Scientific and Technical Emphasis (grant No. 072102270006).

References

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