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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2370.
Published online 2008 November 20. doi:  10.1107/S1600536808037276
PMCID: PMC2959938

N′-[(5-Methyl­furan-2-yl)methyl­ene]isonicotinohydrazide

Abstract

The title compound, C12H11N3O2, was prepared by the reaction of isonicotinohydrazide and 5-methyl­furan-2-carbalde­hyde. The pyridine ring makes a dihedral angle of 46.90 (9)° with the mean plane of the furan ring. The crystal packing is stabilized by a bifurcated inter­molecular N—H(...)(N,O) inter­action.

Related literature

For general background, see: Cimerman et al. (1997 [triangle]). For bond-length data, see: Chiu et al. (1998 [triangle]).

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Object name is e-64-o2370-scheme1.jpg

Experimental

Crystal data

  • C12H11N3O2
  • M r = 229.24
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-64-o2370-efi1.jpg
  • a = 17.313 (3) Å
  • c = 15.749 (5) Å
  • V = 4720.5 (18) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 (2) K
  • 0.25 × 0.20 × 0.19 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 14901 measured reflections
  • 2911 independent reflections
  • 2151 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.117
  • S = 1.04
  • 2911 reflections
  • 155 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.14 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/S1600536808037276/at2662sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037276/at2662Isup2.hkl

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

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 describe its structure here.

In the title compound (I) (Fig. 1), the C12—N3 bond length of 1.2812 (17)Å is comparable with C—N double bond [1.284 (2) Å] reported (Chiu et al., 1998). The pyridine ring (N1/C1–C5) makes a dihedral angle of 46.90 (9)°, with the plane of the furan ring (O2/C6–C9).

The crsytal packing is stabilized by intermolecular N—H···O, N—H···N hydrogen bonds (Table 1, Fig. 2).

Experimental

A mixture of the isonicotinohydrazide (0.1 mol), and 5-methylfuran-2-carbaldehyde (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.082 mol, yield 82%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Refinement

All H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances in the range 0.93-0.97 Å and N—H = 0.86 Å, and with Uiso=1.2–1.5Ueq(N,C).

Figures

Fig. 1.
The molecular structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C12H11N3O2Z = 16
Mr = 229.24F000 = 1920
Tetragonal, I41/aDx = 1.290 Mg m3
Hall symbol: -I 4adMo Kα radiation λ = 0.71073 Å
a = 17.313 (3) ÅCell parameters from 4665 reflections
b = 17.313 (3) Åθ = 2.9–27.2º
c = 15.749 (5) ŵ = 0.09 mm1
α = 90ºT = 273 (2) K
β = 90ºBlock, yellow
γ = 90º0.25 × 0.20 × 0.19 mm
V = 4720.5 (18) Å3

Data collection

Bruker SMART CCD area-detector diffractometer2151 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Monochromator: graphiteθmax = 28.3º
T = 273(2) Kθmin = 1.8º
[var phi] and ω scansh = −16→23
Absorption correction: nonek = −22→22
14901 measured reflectionsl = −20→20
2911 independent reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041  w = 1/[σ2(Fo2) + (0.0456P)2 + 2.257P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.117(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.17 e Å3
2911 reflectionsΔρmin = −0.14 e Å3
155 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0031 (3)
Secondary atom site location: difference Fourier map

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
O20.58347 (5)0.51303 (5)0.10958 (6)0.0482 (3)
N30.72302 (6)0.49350 (7)0.03623 (7)0.0427 (3)
C120.67464 (8)0.53721 (7)−0.00223 (9)0.0423 (3)
H12A0.68660.5578−0.05520.051*
N20.79076 (6)0.47620 (7)−0.00603 (7)0.0443 (3)
H2A0.79800.4901−0.05780.053*
C80.60143 (8)0.55421 (7)0.03726 (8)0.0417 (3)
O10.83833 (7)0.42110 (8)0.11302 (7)0.0750 (4)
C40.91448 (8)0.41092 (8)−0.01179 (8)0.0442 (3)
C110.84487 (8)0.43670 (9)0.03721 (8)0.0460 (3)
C90.51105 (8)0.53616 (9)0.13450 (10)0.0513 (4)
C70.54259 (8)0.60254 (8)0.01805 (10)0.0505 (4)
H7A0.54020.6366−0.02760.061*
C30.91374 (8)0.39635 (10)−0.09860 (9)0.0531 (4)
H3B0.86960.4056−0.13070.064*
N11.04629 (8)0.35518 (10)−0.09513 (9)0.0736 (5)
C50.98256 (9)0.39741 (11)0.03194 (10)0.0640 (5)
H5A0.98530.40610.09010.077*
C20.98006 (9)0.36780 (11)−0.13609 (10)0.0650 (5)
H2B0.97840.3566−0.19380.078*
C60.48512 (9)0.59116 (9)0.08124 (11)0.0561 (4)
H6A0.43820.61700.08510.067*
C11.04634 (10)0.37078 (13)−0.01203 (12)0.0758 (6)
H1B1.09200.36330.01800.091*
C100.47813 (11)0.49172 (12)0.20700 (12)0.0760 (6)
H10A0.42770.51130.22030.114*
H10B0.51120.49710.25560.114*
H10C0.47430.43820.19180.114*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O20.0471 (5)0.0516 (6)0.0459 (6)0.0050 (4)0.0087 (4)0.0080 (4)
N30.0440 (6)0.0466 (6)0.0374 (6)0.0030 (5)0.0080 (5)0.0042 (5)
C120.0482 (7)0.0410 (7)0.0377 (7)−0.0013 (5)0.0043 (5)0.0035 (5)
N20.0455 (6)0.0564 (7)0.0309 (5)0.0060 (5)0.0089 (4)0.0086 (5)
C80.0469 (7)0.0390 (7)0.0393 (7)−0.0019 (5)0.0027 (5)0.0022 (5)
O10.0740 (8)0.1156 (10)0.0355 (6)0.0391 (7)0.0150 (5)0.0225 (6)
C40.0432 (7)0.0547 (8)0.0346 (7)0.0036 (6)0.0027 (5)0.0012 (6)
C110.0493 (8)0.0564 (8)0.0324 (7)0.0078 (6)0.0065 (5)0.0053 (6)
C90.0462 (8)0.0537 (8)0.0540 (9)0.0000 (6)0.0107 (6)−0.0028 (7)
C70.0529 (8)0.0440 (7)0.0545 (9)0.0040 (6)0.0006 (6)0.0051 (6)
C30.0429 (7)0.0785 (10)0.0379 (7)0.0050 (7)−0.0012 (6)−0.0047 (7)
N10.0497 (8)0.1162 (13)0.0550 (8)0.0166 (8)0.0024 (6)−0.0196 (8)
C50.0577 (9)0.0961 (13)0.0381 (8)0.0182 (9)−0.0062 (7)−0.0109 (8)
C20.0546 (9)0.1006 (13)0.0399 (8)0.0090 (9)0.0034 (7)−0.0151 (8)
C60.0468 (8)0.0544 (9)0.0672 (10)0.0085 (6)0.0047 (7)−0.0014 (7)
C10.0483 (9)0.1212 (16)0.0579 (10)0.0220 (10)−0.0099 (7)−0.0188 (10)
C100.0718 (12)0.0839 (13)0.0722 (12)0.0022 (9)0.0292 (9)0.0134 (10)

Geometric parameters (Å, °)

O2—C91.3735 (16)C7—C61.421 (2)
O2—C81.3793 (16)C7—H7A0.9300
N3—C121.2812 (17)C3—C21.383 (2)
N3—N21.3813 (15)C3—H3B0.9300
C12—C81.4421 (18)N1—C21.334 (2)
C12—H12A0.9300N1—C11.336 (2)
N2—C111.3450 (17)C5—C11.383 (2)
N2—H2A0.8600C5—H5A0.9300
C8—C71.3526 (19)C2—H2B0.9300
O1—C111.2293 (16)C6—H6A0.9300
C4—C51.385 (2)C1—H1B0.9300
C4—C31.3904 (19)C10—H10A0.9600
C4—C111.4990 (18)C10—H10B0.9600
C9—C61.346 (2)C10—H10C0.9600
C9—C101.490 (2)
C9—O2—C8106.92 (11)C2—C3—C4118.50 (14)
C12—N3—N2117.08 (11)C2—C3—H3B120.7
N3—C12—C8119.42 (12)C4—C3—H3B120.7
N3—C12—H12A120.3C2—N1—C1116.18 (14)
C8—C12—H12A120.3C1—C5—C4119.14 (14)
C11—N2—N3117.23 (11)C1—C5—H5A120.4
C11—N2—H2A121.4C4—C5—H5A120.4
N3—N2—H2A121.4N1—C2—C3124.47 (14)
C7—C8—O2109.55 (12)N1—C2—H2B117.8
C7—C8—C12133.77 (13)C3—C2—H2B117.8
O2—C8—C12116.66 (11)C9—C6—C7107.52 (13)
C5—C4—C3117.78 (13)C9—C6—H6A126.2
C5—C4—C11118.59 (12)C7—C6—H6A126.2
C3—C4—C11123.56 (12)N1—C1—C5123.88 (15)
O1—C11—N2122.64 (12)N1—C1—H1B118.1
O1—C11—C4120.56 (13)C5—C1—H1B118.1
N2—C11—C4116.79 (11)C9—C10—H10A109.5
C6—C9—O2109.43 (13)C9—C10—H10B109.5
C6—C9—C10135.66 (15)H10A—C10—H10B109.5
O2—C9—C10114.68 (14)C9—C10—H10C109.5
C8—C7—C6106.55 (13)H10A—C10—H10C109.5
C8—C7—H7A126.7H10B—C10—H10C109.5
C6—C7—H7A126.7

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.862.182.9083 (19)143
N2—H2A···N3i0.862.583.3255 (19)146

Symmetry codes: (i) −y+5/4, x−1/4, z−1/4.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2662).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chiu, P., Chen, B. & Cheng, K. F. (1998). Tetrahedron Lett 39, 9229–9232.
  • 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