N′-(But-2-enyl­idene)­iso­nicotino­hydrazide

Yin, Z.-G.; Li, S.-M.; Qian, H.-Y.; Chen, Y.-Z.

doi:10.1107/S1600536808033266

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2150

doi:10.1107/S1600536808033266

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N′-(But-2-enylidene)isonicotinohydrazide

Zhi-Gang Yin,^a ^* Shu-Mian Li,^b Heng-Yu Qian ^a and Yu-Zhen Chen ^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, and ^bSchool of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450052, People's Republic of China
^*Correspondence e-mail: yinck@263.net

(Received 10 October 2008; accepted 13 October 2008; online 22 October 2008)

In the title Schiff base compound, C₁₀H₁₁N₃O, the pyridine ring is twisted with respect to the mean plane containing the hydrazine chain, making a dihedral angle of 31.40 (9)°. The NH group interacts with the N atom of the pyridine ring through N—H⋯N hydrogen bonds to build up a zigzag chain developing parallel to the ( $[\overline{1}]$ 01) plane.

Related literature

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

Experimental

Crystal data

C₁₀H₁₁N₃O
M_r = 189.22
Monoclinic, C c
a = 9.5779 (8) Å
b = 12.6191 (11) Å
c = 9.2095 (8) Å
β = 113.511 (1)°
V = 1020.70 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.25 × 0.23 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.969, T_max = 0.974
4639 measured reflections
1264 independent reflections
1225 reflections with I > 2σ(I)
R_int = 0.012

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.101
S = 1.08
1264 reflections
128 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N3ⁱ	0.86	2.17	2.991 (2)	160
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536808033266/dn2392sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033266/dn2392Isup2.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.

In the title compound. the pyridine ring is twisted with respect to the mean plane containing the hydrazine chain making a dihedral angle of 31.40 (9)° (Fig. 1). The NH interacts with the nitrogen atom of the pyridine ring through N-H···N hydrogen bond to build up a zig-zag chain developing parallel to the (-1 0 1) plane (Table 1, Fig. 2).

Related literature top

For general 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, 3,4-dichlorobenzyaldehyde (1 mmol 0.070 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 presented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view showing the formation of the zig-zag chain through N-H···N hydrogen bonds which are shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity.[Symmetry code: (i) x-1/2, -y+3/2, z-1/2]

N'-(But-2-enylidene)isonicotinohydrazide top

Crystal data top

C₁₀H₁₁N₃O	F(000) = 400
M_r = 189.22	D_x = 1.231 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2994 reflections
a = 9.5779 (8) Å	θ = 2.4–23.8°
b = 12.6191 (11) Å	µ = 0.08 mm⁻¹
c = 9.2095 (8) Å	T = 293 K
β = 113.511 (1)°	Block, brown
V = 1020.70 (15) Å³	0.25 × 0.23 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	1264 independent reflections
Radiation source: fine-focus sealed tube	1225 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
ω scans	θ_max = 28.3°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −12→12
T_min = 0.969, T_max = 0.974	k = −16→16
4639 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0744P)² + 0.0728P] where P = (F_o² + 2F_c²)/3
1264 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.21 e Å⁻³
2 restraints	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₁₀H₁₁N₃O	V = 1020.70 (15) Å³
M_r = 189.22	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 9.5779 (8) Å	µ = 0.08 mm⁻¹
b = 12.6191 (11) Å	T = 293 K
c = 9.2095 (8) Å	0.25 × 0.23 × 0.18 mm
β = 113.511 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1264 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1225 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.974	R_int = 0.012
4639 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	2 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.08	Δρ_max = 0.21 e Å⁻³
1264 reflections	Δρ_min = −0.12 e Å⁻³
128 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
N1	0.12133 (17)	1.06196 (12)	0.79852 (17)	0.0441 (3)
N2	0.21940 (16)	0.98057 (11)	0.87720 (16)	0.0398 (3)
H2	0.2126	0.9200	0.8322	0.048*
N3	0.6220 (2)	0.73212 (13)	1.2278 (2)	0.0512 (4)
O1	0.33989 (17)	1.07888 (10)	1.10035 (17)	0.0542 (4)
C1	−0.2651 (3)	1.1633 (3)	0.2819 (3)	0.0800 (8)
H1A	−0.2643	1.2313	0.3292	0.120*
H1B	−0.3661	1.1344	0.2431	0.120*
H1C	−0.2337	1.1712	0.1957	0.120*
C2	−0.1590 (3)	1.0910 (2)	0.4019 (3)	0.0625 (5)
H2A	−0.1514	1.0222	0.3696	0.075*
C3	−0.0728 (2)	1.11582 (19)	0.5528 (2)	0.0546 (5)
H3	−0.0819	1.1824	0.5913	0.066*
C4	0.0338 (2)	1.04042 (16)	0.6560 (2)	0.0475 (4)
H4	0.0388	0.9732	0.6170	0.057*
C5	0.32562 (18)	0.99674 (12)	1.02479 (18)	0.0366 (3)
C6	0.42972 (17)	0.90326 (12)	1.09198 (17)	0.0362 (3)
C7	0.4905 (3)	0.88762 (17)	1.2543 (2)	0.0529 (5)
H7	0.4696	0.9347	1.3208	0.064*
C8	0.5828 (3)	0.80039 (19)	1.3153 (2)	0.0584 (5)
H8	0.6198	0.7887	1.4239	0.070*
C9	0.5679 (2)	0.75022 (15)	1.0721 (2)	0.0477 (4)
H9	0.5965	0.7046	1.0096	0.057*
C10	0.47069 (19)	0.83399 (13)	0.99866 (19)	0.0411 (3)
H10	0.4341	0.8433	0.8896	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0439 (8)	0.0368 (7)	0.0431 (8)	0.0086 (6)	0.0081 (6)	0.0041 (6)
N2	0.0428 (7)	0.0303 (6)	0.0381 (7)	0.0045 (5)	0.0075 (5)	−0.0011 (5)
N3	0.0596 (9)	0.0426 (8)	0.0425 (8)	0.0149 (7)	0.0108 (7)	0.0071 (6)
O1	0.0604 (8)	0.0401 (7)	0.0468 (7)	0.0119 (6)	0.0055 (6)	−0.0113 (5)
C1	0.0650 (15)	0.099 (2)	0.0570 (13)	0.0146 (14)	0.0046 (11)	0.0212 (14)
C2	0.0564 (11)	0.0683 (14)	0.0532 (12)	0.0083 (10)	0.0116 (9)	0.0077 (10)
C3	0.0481 (9)	0.0564 (11)	0.0491 (10)	0.0114 (8)	0.0086 (8)	0.0117 (8)
C4	0.0453 (9)	0.0441 (9)	0.0445 (9)	0.0048 (7)	0.0088 (7)	0.0027 (7)
C5	0.0387 (7)	0.0320 (7)	0.0351 (7)	0.0046 (5)	0.0104 (6)	−0.0001 (5)
C6	0.0381 (7)	0.0322 (7)	0.0338 (7)	0.0025 (5)	0.0096 (6)	−0.0003 (6)
C7	0.0662 (12)	0.0525 (11)	0.0334 (8)	0.0194 (9)	0.0128 (8)	−0.0008 (7)
C8	0.0720 (12)	0.0601 (12)	0.0334 (8)	0.0204 (10)	0.0108 (8)	0.0074 (8)
C9	0.0585 (10)	0.0395 (8)	0.0423 (8)	0.0146 (7)	0.0173 (8)	0.0013 (6)
C10	0.0494 (8)	0.0366 (8)	0.0332 (7)	0.0088 (6)	0.0122 (6)	0.0014 (6)

Geometric parameters (Å, º) top

N1—C4	1.273 (2)	C3—C4	1.441 (3)
N1—N2	1.3853 (18)	C3—H3	0.9300
N2—C5	1.349 (2)	C4—H4	0.9300
N2—H2	0.8600	C5—C6	1.509 (2)
N3—C8	1.332 (3)	C6—C7	1.385 (2)
N3—C9	1.335 (2)	C6—C10	1.388 (2)
O1—C5	1.225 (2)	C7—C8	1.383 (3)
C1—C2	1.480 (3)	C7—H7	0.9300
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—C10	1.392 (2)
C1—H1C	0.9600	C9—H9	0.9300
C2—C3	1.340 (3)	C10—H10	0.9300
C2—H2A	0.9300

C4—N1—N2	114.28 (15)	C3—C4—H4	118.6
C5—N2—N1	119.75 (13)	O1—C5—N2	124.64 (15)
C5—N2—H2	120.1	O1—C5—C6	121.51 (15)
N1—N2—H2	120.1	N2—C5—C6	113.84 (13)
C8—N3—C9	117.17 (16)	C7—C6—C10	118.54 (14)
C2—C1—H1A	109.5	C7—C6—C5	118.58 (14)
C2—C1—H1B	109.5	C10—C6—C5	122.85 (14)
H1A—C1—H1B	109.5	C8—C7—C6	118.48 (16)
C2—C1—H1C	109.5	C8—C7—H7	120.8
H1A—C1—H1C	109.5	C6—C7—H7	120.8
H1B—C1—H1C	109.5	N3—C8—C7	123.92 (17)
C3—C2—C1	125.9 (2)	N3—C8—H8	118.0
C3—C2—H2A	117.1	C7—C8—H8	118.0
C1—C2—H2A	117.1	N3—C9—C10	123.32 (16)
C2—C3—C4	120.8 (2)	N3—C9—H9	118.3
C2—C3—H3	119.6	C10—C9—H9	118.3
C4—C3—H3	119.6	C6—C10—C9	118.48 (15)
N1—C4—C3	122.76 (18)	C6—C10—H10	120.8
N1—C4—H4	118.6	C9—C10—H10	120.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3ⁱ	0.86	2.17	2.991 (2)	160

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁N₃O
M_r	189.22
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	9.5779 (8), 12.6191 (11), 9.2095 (8)
β (°)	113.511 (1)
V (Å³)	1020.70 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.23 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.969, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	4639, 1264, 1225
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.101, 1.08
No. of reflections	1264
No. of parameters	128
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.12

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—H2···N3ⁱ	0.86	2.17	2.991 (2)	160.3

Symmetry code: (i) x−1/2, −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

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Kahwa, I. A., Selbin, I., Hsieh, T. C. Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179–185. CrossRef CAS Web of Science Google Scholar
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar