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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2150.
Published online 2008 October 22. doi:  10.1107/S1600536808033266
PMCID: PMC2959776

N′-(But-2-enyl­idene)­iso­nicotino­hydrazide

Abstract

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 (An external file that holds a picture, illustration, etc.
Object name is e-64-o2150-efi4.jpg01) plane.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-o2150-scheme1.jpg

Experimental

Crystal data

  • C10H11N3O
  • M r = 189.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2150-efi5.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.101
  • S = 1.08
  • 1264 reflections
  • 128 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.12 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033266/dn2392sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033266/dn2392Isup2.hkl

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

Acknowledgments

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)

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

H atoms were placed in calculated position and treated as riding with C—H= 0.93Å (aromatic), 0.96Å(methyl) and N-H= 0.86\%A with Uiso(H)=1.2Ueq(C,N) or Uiso(H)=1.5Ueq(methyl).

In the absence of significant anomalous scattering, the absolute structure could not be reliably determined and then the Friedel pairs were merged and any references to the Flack parameter were removed.

Figures

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, ...

Crystal data

C10H11N3OF(000) = 400
Mr = 189.22Dx = 1.231 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 2994 reflections
a = 9.5779 (8) Åθ = 2.4–23.8°
b = 12.6191 (11) ŵ = 0.08 mm1
c = 9.2095 (8) ÅT = 293 K
β = 113.511 (1)°Block, brown
V = 1020.70 (15) Å30.25 × 0.23 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer1264 independent reflections
Radiation source: fine-focus sealed tube1225 reflections with I > 2σ(I)
graphiteRint = 0.012
ω scansθmax = 28.3°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 1998)h = −12→12
Tmin = 0.969, Tmax = 0.974k = −16→16
4639 measured reflectionsl = −12→12

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0744P)2 + 0.0728P] where P = (Fo2 + 2Fc2)/3
1264 reflections(Δ/σ)max < 0.001
128 parametersΔρmax = 0.21 e Å3
2 restraintsΔρmin = −0.12 e Å3

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 > 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)

xyzUiso*/Ueq
N10.12133 (17)1.06196 (12)0.79852 (17)0.0441 (3)
N20.21940 (16)0.98057 (11)0.87720 (16)0.0398 (3)
H20.21260.92000.83220.048*
N30.6220 (2)0.73212 (13)1.2278 (2)0.0512 (4)
O10.33989 (17)1.07888 (10)1.10035 (17)0.0542 (4)
C1−0.2651 (3)1.1633 (3)0.2819 (3)0.0800 (8)
H1A−0.26431.23130.32920.120*
H1B−0.36611.13440.24310.120*
H1C−0.23371.17120.19570.120*
C2−0.1590 (3)1.0910 (2)0.4019 (3)0.0625 (5)
H2A−0.15141.02220.36960.075*
C3−0.0728 (2)1.11582 (19)0.5528 (2)0.0546 (5)
H3−0.08191.18240.59130.066*
C40.0338 (2)1.04042 (16)0.6560 (2)0.0475 (4)
H40.03880.97320.61700.057*
C50.32562 (18)0.99674 (12)1.02479 (18)0.0366 (3)
C60.42972 (17)0.90326 (12)1.09198 (17)0.0362 (3)
C70.4905 (3)0.88762 (17)1.2543 (2)0.0529 (5)
H70.46960.93471.32080.064*
C80.5828 (3)0.80039 (19)1.3153 (2)0.0584 (5)
H80.61980.78871.42390.070*
C90.5679 (2)0.75022 (15)1.0721 (2)0.0477 (4)
H90.59650.70461.00960.057*
C100.47069 (19)0.83399 (13)0.99866 (19)0.0411 (3)
H100.43410.84330.88960.049*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0439 (8)0.0368 (7)0.0431 (8)0.0086 (6)0.0081 (6)0.0041 (6)
N20.0428 (7)0.0303 (6)0.0381 (7)0.0045 (5)0.0075 (5)−0.0011 (5)
N30.0596 (9)0.0426 (8)0.0425 (8)0.0149 (7)0.0108 (7)0.0071 (6)
O10.0604 (8)0.0401 (7)0.0468 (7)0.0119 (6)0.0055 (6)−0.0113 (5)
C10.0650 (15)0.099 (2)0.0570 (13)0.0146 (14)0.0046 (11)0.0212 (14)
C20.0564 (11)0.0683 (14)0.0532 (12)0.0083 (10)0.0116 (9)0.0077 (10)
C30.0481 (9)0.0564 (11)0.0491 (10)0.0114 (8)0.0086 (8)0.0117 (8)
C40.0453 (9)0.0441 (9)0.0445 (9)0.0048 (7)0.0088 (7)0.0027 (7)
C50.0387 (7)0.0320 (7)0.0351 (7)0.0046 (5)0.0104 (6)−0.0001 (5)
C60.0381 (7)0.0322 (7)0.0338 (7)0.0025 (5)0.0096 (6)−0.0003 (6)
C70.0662 (12)0.0525 (11)0.0334 (8)0.0194 (9)0.0128 (8)−0.0008 (7)
C80.0720 (12)0.0601 (12)0.0334 (8)0.0204 (10)0.0108 (8)0.0074 (8)
C90.0585 (10)0.0395 (8)0.0423 (8)0.0146 (7)0.0173 (8)0.0013 (6)
C100.0494 (8)0.0366 (8)0.0332 (7)0.0088 (6)0.0122 (6)0.0014 (6)

Geometric parameters (Å, °)

N1—C41.273 (2)C3—C41.441 (3)
N1—N21.3853 (18)C3—H30.9300
N2—C51.349 (2)C4—H40.9300
N2—H20.8600C5—C61.509 (2)
N3—C81.332 (3)C6—C71.385 (2)
N3—C91.335 (2)C6—C101.388 (2)
O1—C51.225 (2)C7—C81.383 (3)
C1—C21.480 (3)C7—H70.9300
C1—H1A0.9600C8—H80.9300
C1—H1B0.9600C9—C101.392 (2)
C1—H1C0.9600C9—H90.9300
C2—C31.340 (3)C10—H100.9300
C2—H2A0.9300
C4—N1—N2114.28 (15)C3—C4—H4118.6
C5—N2—N1119.75 (13)O1—C5—N2124.64 (15)
C5—N2—H2120.1O1—C5—C6121.51 (15)
N1—N2—H2120.1N2—C5—C6113.84 (13)
C8—N3—C9117.17 (16)C7—C6—C10118.54 (14)
C2—C1—H1A109.5C7—C6—C5118.58 (14)
C2—C1—H1B109.5C10—C6—C5122.85 (14)
H1A—C1—H1B109.5C8—C7—C6118.48 (16)
C2—C1—H1C109.5C8—C7—H7120.8
H1A—C1—H1C109.5C6—C7—H7120.8
H1B—C1—H1C109.5N3—C8—C7123.92 (17)
C3—C2—C1125.9 (2)N3—C8—H8118.0
C3—C2—H2A117.1C7—C8—H8118.0
C1—C2—H2A117.1N3—C9—C10123.32 (16)
C2—C3—C4120.8 (2)N3—C9—H9118.3
C2—C3—H3119.6C10—C9—H9118.3
C4—C3—H3119.6C6—C10—C9118.48 (15)
N1—C4—C3122.76 (18)C6—C10—H10120.8
N1—C4—H4118.6C9—C10—H10120.8

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···N3i0.862.172.991 (2)160

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2392).

References

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography