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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1720.
Published online 2010 June 18. doi:  10.1107/S1600536810021471
PMCID: PMC3006900

N′-Benzyl­idene­furan-2-carbohydrazide

Abstract

In the title compound, C12H10N2O2, the dihedral angle between the benzene ring and the furan ring is 24.6 (2)°. In the crystal, mol­ecules are linked by N—H(...)O hydrogen bonds, generating C(4) chains propagating in [010].

Related literature

For background to Schiff bases as ligands, see: Polt et al. (2003 [triangle]). For a related structure, see: Jiang (2010 [triangle]).

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Object name is e-66-o1720-scheme1.jpg

Experimental

Crystal data

  • C12H10N2O2
  • M r = 214.22
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1720-efi1.jpg
  • a = 11.628 (2) Å
  • b = 7.6638 (15) Å
  • c = 23.873 (5) Å
  • V = 2127.4 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.22 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD diffractometer
  • 15748 measured reflections
  • 1915 independent reflections
  • 841 reflections with I > 2σ(I)
  • R int = 0.180

Refinement

  • R[F 2 > 2σ(F 2)] = 0.069
  • wR(F 2) = 0.182
  • S = 0.87
  • 1915 reflections
  • 146 parameters
  • H-atom parameters constrained
  • Δρmax = 0.48 e Å−3
  • Δρmin = −0.35 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/S1600536810021471/hb5485sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021471/hb5485Isup2.hkl

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

supplementary crystallographic information

Comment

Metal complexes based on Schiff bases have attracted much attention because they can be utilized as effective ligands to form the compounds with optically active (Polt et al., 2003). As part of our search for new Schiff base compounds we synthesized the title compound (I), and describe its structure here. The dihedral angle between the benzene ring and the furan ring is 24.6 (2)°. In the crystal lattice, the N—H···O hydrogen bonds which form chains stable the molecule structures.

Bond lengths and angles are comparable to those in a related material (Jiang, 2010).

Experimental

A mixture of benzaldehyde (0.1 mol), and furan-2-carbohydrazide (0.1 mol) was stirred in refluxing ethanol (20 ml) for 2 h to afford the title compound (0.096 mol, yield 96%). Colourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.

Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances=0.97 Å, and with Uiso=1.2–1.5Ueq.

Figures

Fig. 1.
The structure of (I) showing 30% probability displacement ellipsoids.

Crystal data

C12H10N2O2F(000) = 896
Mr = 214.22Dx = 1.338 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2542 reflections
a = 11.628 (2) Åθ = 2.7–25.4°
b = 7.6638 (15) ŵ = 0.09 mm1
c = 23.873 (5) ÅT = 293 K
V = 2127.4 (7) Å3Block, colorless
Z = 80.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer841 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.180
graphiteθmax = 25.3°, θmin = 3.3°
phi and ω scansh = −13→13
15748 measured reflectionsk = −9→9
1915 independent reflectionsl = −28→28

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.182w = 1/[σ2(Fo2) + (0.0916P)2] where P = (Fo2 + 2Fc2)/3
S = 0.87(Δ/σ)max < 0.001
1915 reflectionsΔρmax = 0.48 e Å3
146 parametersΔρmin = −0.35 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.042 (4)

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
C70.6392 (3)0.2814 (4)0.22579 (15)0.0427 (9)
N20.7400 (2)0.2911 (4)0.13973 (12)0.0444 (8)
O20.89248 (19)0.4222 (3)0.06644 (10)0.0525 (7)
C60.6608 (3)0.2226 (4)0.16890 (15)0.0464 (9)
H6A0.61610.13380.15370.056*
N10.7595 (2)0.2165 (4)0.08817 (12)0.0468 (8)
H1A0.72040.12730.07740.056*
C110.5250 (3)0.2748 (5)0.30936 (18)0.0614 (11)
H11A0.45990.23570.32820.074*
C50.8408 (3)0.2861 (4)0.05515 (15)0.0433 (9)
O10.8127 (2)0.0388 (3)−0.00680 (11)0.0624 (8)
C120.5431 (3)0.2243 (5)0.25478 (17)0.0565 (11)
H12A0.49050.15110.23720.068*
C20.9298 (4)0.0939 (6)−0.07761 (19)0.0717 (13)
H2B0.96970.0836−0.11120.086*
C80.7157 (3)0.3882 (5)0.25381 (16)0.0499 (10)
H8A0.78160.42620.23540.060*
C40.8663 (3)0.1949 (4)0.00321 (15)0.0457 (9)
C30.9374 (3)0.2318 (5)−0.03877 (18)0.0619 (12)
H4A0.98350.3304−0.04190.074*
C100.6010 (4)0.3816 (5)0.33627 (18)0.0617 (11)
H10A0.58840.41480.37320.074*
C90.6968 (3)0.4393 (5)0.30781 (17)0.0607 (11)
H9A0.74880.51340.32540.073*
C10.8544 (4)−0.0182 (6)−0.05660 (18)0.0746 (13)
H1B0.8329−0.1222−0.07370.090*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C70.047 (2)0.0397 (19)0.042 (2)0.0015 (16)0.0025 (17)0.0011 (17)
N20.0508 (17)0.0434 (17)0.0389 (19)−0.0018 (14)0.0016 (14)−0.0050 (14)
O20.0574 (14)0.0490 (15)0.0512 (18)−0.0076 (12)0.0024 (13)−0.0054 (12)
C60.052 (2)0.0403 (19)0.047 (2)−0.0016 (17)−0.0001 (19)−0.0025 (17)
N10.0558 (18)0.0463 (17)0.0384 (19)−0.0070 (14)0.0023 (15)−0.0081 (14)
C110.058 (2)0.073 (3)0.054 (3)0.005 (2)0.019 (2)0.001 (2)
C50.0469 (19)0.0411 (19)0.042 (2)0.0030 (17)−0.0022 (18)0.0021 (18)
O10.0769 (18)0.0604 (17)0.0499 (19)−0.0157 (13)0.0153 (14)−0.0151 (13)
C120.051 (2)0.060 (2)0.059 (3)−0.0034 (19)0.007 (2)−0.006 (2)
C20.085 (3)0.080 (3)0.051 (3)−0.011 (2)0.024 (2)−0.006 (2)
C80.051 (2)0.051 (2)0.047 (3)−0.0037 (18)0.0013 (19)−0.0039 (18)
C40.051 (2)0.0434 (19)0.043 (3)−0.0017 (16)−0.0007 (18)−0.0012 (18)
C30.070 (3)0.062 (3)0.053 (3)−0.010 (2)0.012 (2)−0.005 (2)
C100.080 (3)0.068 (3)0.038 (2)0.016 (2)0.007 (2)−0.001 (2)
C90.073 (3)0.062 (3)0.048 (3)0.002 (2)−0.003 (2)−0.010 (2)
C10.101 (3)0.069 (3)0.053 (3)−0.007 (3)0.019 (2)−0.021 (2)

Geometric parameters (Å, °)

C7—C81.382 (5)O1—C41.370 (4)
C7—C121.385 (5)C12—H12A0.9300
C7—C61.453 (5)C2—C11.327 (6)
N2—C61.268 (4)C2—C31.408 (5)
N2—N11.376 (4)C2—H2B0.9300
O2—C51.234 (4)C8—C91.365 (5)
C6—H6A0.9300C8—H8A0.9300
N1—C51.342 (4)C4—C31.329 (5)
N1—H1A0.8600C3—H4A0.9300
C11—C101.366 (5)C10—C91.377 (5)
C11—C121.376 (5)C10—H10A0.9300
C11—H11A0.9300C9—H9A0.9300
C5—C41.454 (5)C1—H1B0.9300
O1—C11.357 (4)
C8—C7—C12117.7 (4)C1—C2—H2B126.9
C8—C7—C6121.6 (3)C3—C2—H2B126.9
C12—C7—C6120.6 (3)C9—C8—C7121.6 (4)
C6—N2—N1116.0 (3)C9—C8—H8A119.2
N2—C6—C7120.7 (3)C7—C8—H8A119.2
N2—C6—H6A119.6C3—C4—O1109.7 (3)
C7—C6—H6A119.6C3—C4—C5131.9 (3)
C5—N1—N2118.4 (3)O1—C4—C5118.4 (3)
C5—N1—H1A120.8C4—C3—C2107.4 (3)
N2—N1—H1A120.8C4—C3—H4A126.3
C10—C11—C12121.0 (4)C2—C3—H4A126.3
C10—C11—H11A119.5C11—C10—C9119.0 (4)
C12—C11—H11A119.5C11—C10—H10A120.5
O2—C5—N1123.5 (3)C9—C10—H10A120.5
O2—C5—C4119.5 (3)C8—C9—C10120.2 (4)
N1—C5—C4117.0 (3)C8—C9—H9A119.9
C1—O1—C4105.8 (3)C10—C9—H9A119.9
C11—C12—C7120.6 (4)C2—C1—O1111.0 (4)
C11—C12—H12A119.7C2—C1—H1B124.5
C7—C12—H12A119.7O1—C1—H1B124.5
C1—C2—C3106.1 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.062.911 (4)168

Symmetry codes: (i) −x+3/2, y−1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5485).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Jiang, J.-H. (2010). Acta Cryst. E66, o627. [PMC free article] [PubMed]
  • Polt, R., Kelly, B. D. & Dangel, B. D. (2003). Inorg. Chem 42, 566–574. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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