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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3125.
Published online 2009 November 21. doi:  10.1107/S1600536809048569
PMCID: PMC2972171

N′-(1-Phenyl­ethyl­idene)isonicotinohydrazide

Abstract

The title compound, C14H13N3O, was prepared from hypnone and isoniazid. The dihedral angle between the aromatic rings is 12.21 (2)°. In the crystal, N—H(...)O hydrogen bonds link the mol­ecules into chains propagating in [001] and C—H(...)O inter­actions consolidate the packing.

Related literature

For background on Schiff bases, see: Cimerman et al. (1997 [triangle]). For a related structure, see: Chen et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o3125-scheme1.jpg

Experimental

Crystal data

  • C14H13N3O
  • M r = 239.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3125-efi1.jpg
  • a = 25.878 (5) Å
  • b = 5.7100 (11) Å
  • c = 8.3089 (17) Å
  • β = 90.94 (3)°
  • V = 1227.6 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.35 × 0.25 × 0.25 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: none
  • 11394 measured reflections
  • 2821 independent reflections
  • 2024 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.068
  • wR(F 2) = 0.205
  • S = 1.03
  • 2821 reflections
  • 167 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048569/hb5224sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048569/hb5224Isup2.hkl

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

Acknowledgments

The authors would like to thank the National Natural Science Foundation of Shandong Province (Y2008B29) and the Yuandu Scholar Fund of Weifang City for support.

supplementary crystallographic information

Comment

Schiff bases have received considerable attention in the literature. They 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) and report its crystal structure herein.

In the title compound (I) (Fig. 1), the C8=N2 bond, 1.285 (3) Å, and the C6—N3 bond, 1.351 (3) Å, are both longer than those in a related compound (Chen et al., 2006). All other bond lengths are within normal ranges. The dihedral angle between the benzene and pyridine rings is 12.21 (2)°. The structure of (I) is stabilized by C—H···O,N—H···O and C—H···N hydrogen bonds (Table 1).

Experimental

A mixture of the isoniazid (0.05 mol) and hypnone (0.05 mol) was stirred in refluxing ethanol(30 ml) for 2 h to afford the title compound (yield 78%). Colourless bars of (I) were obtained by recrystallization from ethanol at room temperature.

Refinement

The N-bound H atom was located in a difference map and freely refined. The other H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances = 0.97 Å, and Uiso(H) = 1.2–1.5Ueq(C).

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.

Crystal data

C14H13N3OF(000) = 504
Mr = 239.27Dx = 1.295 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2024 reflections
a = 25.878 (5) Åθ = 3.2–27.5°
b = 5.7100 (11) ŵ = 0.09 mm1
c = 8.3089 (17) ÅT = 293 K
β = 90.94 (3)°Bar, colourless
V = 1227.6 (4) Å30.35 × 0.25 × 0.25 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer2024 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
graphiteθmax = 27.5°, θmin = 3.2°
ω scansh = −33→33
11394 measured reflectionsk = −7→7
2821 independent reflectionsl = −9→10

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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.205H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.1014P)2 + 0.6215P] where P = (Fo2 + 2Fc2)/3
2821 reflections(Δ/σ)max < 0.001
167 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.29 e Å3

Special details

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)

xyzUiso*/Ueq
N30.28050 (6)0.2893 (3)0.9742 (2)0.0401 (4)
N20.23151 (7)0.3104 (3)1.0394 (2)0.0414 (5)
C60.31164 (7)0.1224 (4)1.0382 (2)0.0366 (5)
O10.30052 (6)0.0099 (3)1.15887 (18)0.0472 (4)
C90.15153 (7)0.4982 (4)1.0663 (2)0.0364 (5)
C80.20515 (8)0.4938 (4)1.0019 (2)0.0356 (5)
C30.36258 (7)0.0813 (4)0.9583 (2)0.0375 (5)
C40.38721 (8)0.2432 (4)0.8623 (3)0.0446 (5)
H4A0.37190.38700.83900.054*
C70.22348 (9)0.6943 (4)0.9029 (3)0.0492 (6)
H7A0.25830.66580.87040.074*
H7B0.22230.83560.96540.074*
H7C0.20160.71070.80920.074*
C100.13477 (8)0.3243 (4)1.1704 (3)0.0476 (6)
H10A0.15740.20581.20210.057*
C130.06659 (9)0.6712 (5)1.0781 (3)0.0591 (7)
H13A0.04370.78871.04680.071*
C110.08489 (9)0.3254 (5)1.2275 (3)0.0564 (7)
H11A0.07440.20921.29820.068*
C140.11683 (9)0.6724 (5)1.0213 (3)0.0501 (6)
H14A0.12730.79110.95240.060*
C20.38778 (9)−0.1288 (5)0.9907 (3)0.0526 (6)
H2B0.3728−0.24141.05610.063*
N10.45942 (8)−0.0143 (5)0.8287 (3)0.0630 (7)
C120.05063 (8)0.4978 (5)1.1801 (3)0.0558 (7)
H12A0.01690.49651.21700.067*
C50.43514 (9)0.1864 (5)0.8015 (3)0.0564 (7)
H5A0.45140.29660.73730.068*
C10.43566 (10)−0.1669 (5)0.9235 (4)0.0658 (8)
H1B0.4523−0.30780.94600.079*
H3A0.2875 (9)0.349 (5)0.881 (3)0.045 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N30.0333 (9)0.0442 (10)0.0431 (9)0.0044 (7)0.0129 (7)0.0055 (8)
N20.0334 (9)0.0454 (11)0.0459 (9)0.0043 (7)0.0134 (7)0.0031 (8)
C60.0323 (9)0.0408 (11)0.0368 (9)−0.0011 (8)0.0055 (8)−0.0025 (8)
O10.0431 (8)0.0558 (11)0.0431 (8)0.0037 (7)0.0106 (7)0.0078 (7)
C90.0321 (9)0.0400 (11)0.0372 (10)0.0010 (8)0.0026 (8)−0.0047 (8)
C80.0348 (10)0.0366 (11)0.0355 (9)0.0004 (8)0.0044 (8)−0.0050 (8)
C30.0308 (9)0.0431 (12)0.0387 (10)−0.0001 (8)0.0042 (8)−0.0065 (9)
C40.0328 (10)0.0499 (13)0.0513 (12)−0.0003 (9)0.0073 (9)0.0020 (10)
C70.0497 (13)0.0392 (13)0.0590 (13)0.0002 (9)0.0154 (11)0.0030 (10)
C100.0359 (11)0.0496 (14)0.0573 (13)0.0044 (9)0.0049 (10)0.0088 (11)
C130.0416 (12)0.0639 (18)0.0720 (17)0.0195 (11)0.0061 (12)0.0028 (13)
C110.0399 (12)0.0642 (17)0.0654 (15)−0.0024 (11)0.0128 (11)0.0112 (13)
C140.0454 (12)0.0478 (14)0.0572 (13)0.0081 (10)0.0071 (11)0.0061 (11)
C20.0435 (12)0.0449 (14)0.0697 (15)0.0046 (10)0.0102 (11)0.0025 (12)
N10.0366 (10)0.0716 (17)0.0813 (16)0.0040 (10)0.0147 (10)−0.0137 (13)
C120.0310 (10)0.0702 (19)0.0662 (15)0.0045 (10)0.0087 (10)−0.0048 (13)
C50.0349 (11)0.0729 (19)0.0619 (14)−0.0045 (11)0.0135 (10)0.0007 (13)
C10.0445 (13)0.0534 (16)0.100 (2)0.0129 (11)0.0110 (14)−0.0080 (15)

Geometric parameters (Å, °)

N3—C61.351 (3)C7—H7C0.9600
N3—N21.392 (2)C10—C111.382 (3)
N3—H3A0.87 (2)C10—H10A0.9300
N2—C81.285 (3)C13—C121.371 (4)
C6—O11.229 (2)C13—C141.391 (3)
C6—C31.504 (3)C13—H13A0.9300
C9—C141.387 (3)C11—C121.378 (4)
C9—C101.391 (3)C11—H11A0.9300
C9—C81.496 (3)C14—H14A0.9300
C8—C71.492 (3)C2—C11.385 (3)
C3—C41.384 (3)C2—H2B0.9300
C3—C21.390 (3)N1—C51.324 (4)
C4—C51.385 (3)N1—C11.332 (4)
C4—H4A0.9300C12—H12A0.9300
C7—H7A0.9600C5—H5A0.9300
C7—H7B0.9600C1—H1B0.9300
C6—N3—N2116.69 (17)C11—C10—C9120.8 (2)
C6—N3—H3A119.8 (16)C11—C10—H10A119.6
N2—N3—H3A121.1 (16)C9—C10—H10A119.6
C8—N2—N3117.33 (18)C12—C13—C14120.4 (2)
O1—C6—N3122.91 (18)C12—C13—H13A119.8
O1—C6—C3119.80 (19)C14—C13—H13A119.8
N3—C6—C3117.27 (18)C12—C11—C10120.4 (2)
C14—C9—C10118.20 (19)C12—C11—H11A119.8
C14—C9—C8121.05 (19)C10—C11—H11A119.8
C10—C9—C8120.74 (18)C9—C14—C13120.6 (2)
N2—C8—C7125.95 (18)C9—C14—H14A119.7
N2—C8—C9114.75 (18)C13—C14—H14A119.7
C7—C8—C9119.30 (18)C1—C2—C3118.5 (2)
C4—C3—C2117.99 (19)C1—C2—H2B120.7
C4—C3—C6124.4 (2)C3—C2—H2B120.7
C2—C3—C6117.5 (2)C5—N1—C1116.4 (2)
C3—C4—C5118.5 (2)C13—C12—C11119.6 (2)
C3—C4—H4A120.8C13—C12—H12A120.2
C5—C4—H4A120.8C11—C12—H12A120.2
C8—C7—H7A109.5N1—C5—C4124.5 (2)
C8—C7—H7B109.5N1—C5—H5A117.8
H7A—C7—H7B109.5C4—C5—H5A117.8
C8—C7—H7C109.5N1—C1—C2124.1 (3)
H7A—C7—H7C109.5N1—C1—H1B117.9
H7B—C7—H7C109.5C2—C1—H1B117.9

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3A···O1i0.87 (2)2.04 (3)2.914 (2)177 (2)
C4—H4A···O1i0.932.433.123 (3)131
C7—H7A···O1i0.962.313.095 (3)138

Symmetry codes: (i) x, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5224).

References

  • Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chen, S.-S., Zhang, S.-P., Huang, C.-B. & Shao, S.-C. (2006). Acta Cryst. E62, o31–o32.
  • Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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