organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: ffjian2008@163.com

(Received 20 October 2008; accepted 13 November 2008; online 22 November 2008)

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[Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145-153.]); Girgis (2006[Girgis, A. S. (2006). J. Chem. Res. pp. 81-85.]). For bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C11H14N2O2

  • Mr = 206.24

  • Monoclinic, P 21 /n

  • 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)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2A⋯O2i 0.86 2.12 2.956 (3) 166
Symmetry code: (i) -x+2, -y, -z+2.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] 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.
N'-[1-(4-Methoxyphenyl)ethylidene]acetohydrazide top
Crystal data top
C11H14N2O2F(000) = 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 = 2.4–24.0°
b = 4.9923 (10) ŵ = 0.09 mm1
c = 16.854 (3) ÅT = 293 K
β = 98.88 (3)°Block, yellow
V = 1104.2 (4) Å30.25 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
1228 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 28.3°, θmin = 1.8°
ϕ and ω scansh = 1715
6830 measured reflectionsk = 66
2681 independent reflectionsl = 1622
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0986P)2 + 0.0719P]
where P = (Fo2 + 2Fc2)/3
2681 reflections(Δ/σ)max < 0.001
137 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C11H14N2O2V = 1104.2 (4) Å3
Mr = 206.24Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.282 (3) ŵ = 0.09 mm1
b = 4.9923 (10) ÅT = 293 K
c = 16.854 (3) Å0.25 × 0.20 × 0.18 mm
β = 98.88 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
1228 reflections with I > 2σ(I)
6830 measured reflectionsRint = 0.035
2681 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.196H-atom parameters constrained
S = 0.93Δρmax = 0.17 e Å3
2681 reflectionsΔρmin = 0.17 e Å3
137 parameters
Special details top

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) top
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*
H9C1.22920.11051.12710.239*
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) top
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, º) top
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, º) top
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 code: (i) x+2, y, z+2.

Experimental details

Crystal data
Chemical formulaC11H14N2O2
Mr206.24
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)13.282 (3), 4.9923 (10), 16.854 (3)
β (°) 98.88 (3)
V3)1104.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.25 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6830, 2681, 1228
Rint0.035
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.196, 0.93
No. of reflections2681
No. of parameters137
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.17

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.862.122.956 (3)166
Symmetry code: (i) x+2, y, z+2.
 

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science
First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153.  CrossRef CAS Web of Science
First citationGirgis, A. S. (2006). J. Chem. Res. pp. 81–85.  CrossRef
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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ISSN: 2056-9890
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