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Volume 69 
Part 9 
Page o1418  
September 2013  

Received 2 August 2013
Accepted 8 August 2013
Online 21 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.098
Data-to-parameter ratio = 14.1
Details
Open access

anti-Ethyl acetohydroximate

aInstitute of Chemistry, University of Silesia, 14 Bankowa Street, 40-007 Katowice, Poland, and bInstitute of Physics, University of Silesia, 4 Uniwersytecka Street, 40-007 Katowice, Poland
Correspondence e-mail: bhachula@o2.pl

In the crystal structure of the title compound, C4H9NO2, the O-H...N hydrogen bonds link the molecules into supramolecular chains extending along the b-axis direction. The conformation of the NOH group in the nearly planar (r.m.s. deviation = 0.0546 Å) ethyl acetohydroximate molecule is trans to N=C.

Related literature

For related structures, see: Kjaer et al. (1977[Kjaer, A., Larsen, I. K. & Sivertsen, P. (1977). Acta Chem. Scand. Ser. B, 31, 415-423.]); Larsen (1971[Larsen, I. K. (1971). Acta Chem. Scand. 25, 2409-2420.]). For studies of the IR spectra of hydrogen bonding in oxime derivatives, see: Flakus et al. (2012[Flakus, H., Hachula, B. & Garbacz, A. (2012). J. Phys. Chem. A116, 11553-11567.]). For typical bond distances, see: Allen et al. (1987[Allen, F. A., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C4H9NO2

  • Mr = 103.12

  • Monoclinic, C 2/c

  • a = 19.9481 (9) Å

  • b = 4.4138 (1) Å

  • c = 13.3277 (5) Å

  • [beta] = 109.027 (4)°

  • V = 1109.35 (7) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.52 × 0.18 × 0.14 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Sapphire3 detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]) Tmin = 0.505, Tmax = 1.000

  • 6699 measured reflections

  • 970 independent reflections

  • 868 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.098

  • S = 1.08

  • 970 reflections

  • 69 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1i 0.871 (19) 1.954 (19) 2.8196 (14) 172.4 (16)
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.]); 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2116 ).


References

Allen, F. A., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Flakus, H., Hachula, B. & Garbacz, A. (2012). J. Phys. Chem. A116, 11553-11567.  [ISI] [CrossRef]
Kjaer, A., Larsen, I. K. & Sivertsen, P. (1977). Acta Chem. Scand. Ser. B, 31, 415-423.
Larsen, I. K. (1971). Acta Chem. Scand. 25, 2409-2420.  [CrossRef]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wroclaw, Poland.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1418  [ doi:10.1107/S1600536813022368 ]

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