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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2409.
Published online 2008 November 22. doi:  10.1107/S1600536808037677
PMCID: PMC2959840

N′-[1-(4-Methoxy­phen­yl)ethyl­idene]acetohydrazide

Abstract

The title compound, C11H14N2O2, was prepared by the reaction of acetohydrazide and 1-(4-methoxy­phen­yl)ethanone. In the mol­ecule, all bond lengths and angles are within normal ranges. In the crystal structure, adjacent mol­ecules are linked into a centrosymmetric dimer by inter­molecular N—H(...)O hydrogen bonding.

Related literature

For related literature, see: Cimerman et al. (1997 [triangle]); Girgis (2006 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-64-o2409-scheme1.jpg

Experimental

Crystal data

  • C11H14N2O2
  • M r = 206.24
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2409-efi1.jpg
  • a = 13.282 (3) Å
  • b = 4.9923 (10) Å
  • c = 16.854 (3) Å
  • β = 98.88 (3)°
  • V = 1104.2 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 (2) K
  • 0.25 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 6830 measured reflections
  • 2681 independent reflections
  • 1228 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.196
  • S = 0.93
  • 2681 reflections
  • 137 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.17 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/S1600536808037677/at2657sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037677/at2657Isup2.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 (Fig. 1), all bond lengths and angles are within normal ranges (Allen et al., 1987). The C8—N1 bond length of 1.278 (3)Å is comparable with C—N double bond [1.281 (2) Å] reported (Girgis, 2006).

In the crystal structure, adjacent molecules are linked into a centro-symmetric supra-molecular dimer by intermolecular N—H···O hydrogen bonding (Table 1, Fig. 2).

Experimental

A mixture of the acetohydrazide (0.1 mol), and 1-(4-methoxyphenyl)ethanone (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.080 mol, yield 80%). Single crystals suitable for X-ray measurements 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 = 0.93-0.96 Å and N—H = 0.86 Å, and with Uiso=1.2–1.5Ueq.

Figures

Fig. 1.
The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
Part of the crystal structure of the title compound showing the formation of a cyclic centrosymmetric dimer. For the sake of clarity, H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C11H14N2O2F000 = 440
Mr = 206.24Dx = 1.241 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 831 reflections
a = 13.282 (3) Åθ = 2.4–24.0º
b = 4.9923 (10) ŵ = 0.09 mm1
c = 16.854 (3) ÅT = 293 (2) K
β = 98.88 (3)ºBlock, yellow
V = 1104.2 (4) Å30.25 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer1228 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Monochromator: graphiteθmax = 28.3º
T = 273(2) Kθmin = 1.8º
[var phi] and ω scansh = −17→15
Absorption correction: nonek = −6→6
6830 measured reflectionsl = −16→22
2681 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.196  w = 1/[σ2(Fo2) + (0.0986P)2 + 0.0719P] where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max < 0.001
2681 reflectionsΔρmax = 0.17 e Å3
137 parametersΔρmin = −0.17 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
O20.98272 (13)0.2016 (4)0.91643 (10)0.0761 (6)
O11.64324 (12)0.8045 (4)1.19345 (10)0.0788 (6)
N21.12429 (14)0.2219 (4)1.00666 (11)0.0631 (6)
H2A1.10370.09251.03380.076*
N11.21780 (14)0.3415 (4)1.03226 (11)0.0608 (5)
C51.36778 (17)0.4053 (4)1.12310 (13)0.0559 (6)
C101.06577 (19)0.3085 (5)0.93934 (14)0.0606 (6)
C81.26860 (17)0.2683 (4)1.09940 (13)0.0572 (6)
C21.55227 (16)0.6811 (5)1.16686 (13)0.0588 (6)
C71.51710 (18)0.5048 (5)1.21885 (14)0.0675 (7)
H7A1.55470.47751.26950.081*
C31.49509 (19)0.7215 (5)1.09293 (15)0.0739 (8)
H3A1.51740.84081.05700.089*
C41.40476 (19)0.5860 (6)1.07177 (14)0.0752 (8)
H4A1.36710.61631.02130.090*
C61.42740 (18)0.3683 (5)1.19720 (13)0.0632 (7)
H6A1.40610.24771.23330.076*
C111.1030 (2)0.5331 (5)0.89359 (15)0.0754 (7)
H11A1.05320.57290.84750.113*
H11B1.16600.48280.87640.113*
H11C1.11370.68860.92730.113*
C91.2343 (2)0.0599 (6)1.15380 (17)0.0931 (10)
H9A1.16890.10901.16680.159 (16)*
H9B1.28280.04821.20220.239*
H9C1.2292−0.11051.12710.239*
C11.68123 (19)0.9957 (5)1.14314 (16)0.0807 (8)
H1B1.74531.06391.16950.121*
H1C1.63351.14041.13240.121*
H1D1.69060.91201.09350.121*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O20.0790 (12)0.0801 (12)0.0670 (11)−0.0227 (10)0.0048 (9)0.0087 (9)
O10.0687 (11)0.0908 (13)0.0735 (12)−0.0172 (10)0.0003 (9)0.0073 (10)
N20.0729 (13)0.0604 (12)0.0562 (12)−0.0161 (10)0.0109 (10)0.0038 (9)
N10.0651 (12)0.0615 (12)0.0562 (12)−0.0126 (9)0.0107 (9)−0.0025 (9)
C50.0640 (13)0.0541 (13)0.0515 (13)−0.0032 (11)0.0153 (11)−0.0005 (10)
C100.0718 (16)0.0557 (14)0.0558 (14)−0.0084 (12)0.0145 (12)−0.0020 (11)
C80.0674 (15)0.0560 (14)0.0506 (13)−0.0047 (12)0.0162 (11)−0.0009 (11)
C20.0598 (14)0.0620 (14)0.0549 (13)0.0000 (11)0.0097 (11)0.0000 (11)
C70.0722 (15)0.0773 (16)0.0510 (13)−0.0031 (14)0.0033 (11)0.0059 (12)
C30.0746 (16)0.0863 (19)0.0598 (15)−0.0177 (15)0.0072 (13)0.0196 (14)
C40.0759 (16)0.0917 (19)0.0542 (14)−0.0197 (15)−0.0016 (12)0.0178 (13)
C60.0768 (16)0.0603 (14)0.0533 (14)−0.0024 (12)0.0130 (12)0.0081 (11)
C110.0877 (17)0.0683 (16)0.0696 (16)−0.0160 (14)0.0099 (13)0.0132 (13)
C90.101 (2)0.097 (2)0.0798 (19)−0.0350 (18)0.0105 (16)0.0259 (17)
C10.0726 (16)0.0842 (19)0.0872 (18)−0.0190 (15)0.0183 (14)0.0019 (16)

Geometric parameters (Å, °)

O2—C101.232 (3)C7—H7A0.9300
O1—C21.369 (3)C3—C41.376 (3)
O1—C11.420 (3)C3—H3A0.9300
N2—C101.344 (3)C4—H4A0.9300
N2—N11.386 (2)C6—H6A0.9300
N2—H2A0.8600C11—H11A0.9600
N1—C81.278 (3)C11—H11B0.9600
C5—C61.384 (3)C11—H11C0.9600
C5—C41.391 (3)C9—H9A0.9600
C5—C81.483 (3)C9—H9B0.9600
C10—C111.488 (3)C9—H9C0.9600
C8—C91.503 (3)C1—H1B0.9600
C2—C31.370 (3)C1—H1C0.9600
C2—C71.374 (3)C1—H1D0.9600
C7—C61.372 (3)
C2—O1—C1118.96 (19)C3—C4—H4A118.8
C10—N2—N1119.9 (2)C5—C4—H4A118.8
C10—N2—H2A120.1C7—C6—C5121.7 (2)
N1—N2—H2A120.1C7—C6—H6A119.1
C8—N1—N2118.54 (19)C5—C6—H6A119.1
C6—C5—C4116.1 (2)C10—C11—H11A109.5
C6—C5—C8122.8 (2)C10—C11—H11B109.5
C4—C5—C8121.0 (2)H11A—C11—H11B109.5
O2—C10—N2119.9 (2)C10—C11—H11C109.5
O2—C10—C11121.1 (2)H11A—C11—H11C109.5
N2—C10—C11119.0 (2)H11B—C11—H11C109.5
N1—C8—C5115.6 (2)C8—C9—H9A109.5
N1—C8—C9124.7 (2)C8—C9—H9B109.5
C5—C8—C9119.7 (2)H9A—C9—H9B109.5
O1—C2—C3124.7 (2)C8—C9—H9C109.5
O1—C2—C7116.7 (2)H9A—C9—H9C109.5
C3—C2—C7118.6 (2)H9B—C9—H9C109.5
C6—C7—C2121.0 (2)O1—C1—H1B109.5
C6—C7—H7A119.5O1—C1—H1C109.5
C2—C7—H7A119.5H1B—C1—H1C109.5
C2—C3—C4120.1 (2)O1—C1—H1D109.5
C2—C3—H3A119.9H1B—C1—H1D109.5
C4—C3—H3A119.9H1C—C1—H1D109.5
C3—C4—C5122.4 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.862.122.956 (3)166
C4—H4A···N10.932.442.755 (3)100

Symmetry codes: (i) −x+2, −y, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2657).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153.
  • Girgis, A. S. (2006). J. Chem. Res. pp. 81–85.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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