(E)-1-(4-Amino­phen­yl)ethanone oxime

Rafiq, M.; Hanif, M.; Qadeer, G.; Vuoti, S.; Autio, J.

doi:10.1107/S1600536808034120

Volume 64
Part 11
Page o2173
November 2008

Received 13 October 2008
Accepted 18 October 2008
Online 22 October 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.040
wR = 0.108
Data-to-parameter ratio = 15.6
Details

(E)-1-(4-Aminophenyl)ethanone oxime

Muhammad Rafiq,^a Muhammad Hanif,^b Ghulam Qadeer,^b Sauli Vuoti ^c and Juho Autio ^c ^*

^aDepartment of Chemistry, BZU, Multan, Pakistan,^bDepartment of Chemistry, Quaid-i-Azam Univeristy, Islamabad 45320, Pakistan, and ^cDepartment of Chemistry, University of Oulu, PO Box 3000, 90014 Finland
Correspondence e-mail: qadeerqau@yahoo.com

In the molecule of the title compound, C₈H₁₀N₂O, the oxime group is oriented at a dihedral angle of 5.58 (3)° with respect to the benzene ring. In the crystal structure, intermolecular O-HN and N-HO hydrogen bonds link the molecules, forming a three-dimensional network.

Related literature

For general background, see: Bertolasi et al. (1982); Degorre et al. (1998). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₈H₁₀N₂O
M_r = 150.18
Monoclinic, P 2₁ /n
a = 4.8641 (2) Å
b = 9.2016 (3) Å
c = 17.1447 (7) Å
= 95.535 (2)°
V = 763.78 (5) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 100 (2) K
0.34 × 0.28 × 0.26 mm

Data collection

Enraf-Nonius KappaCCD diffractometer
Absorption correction: multi-scan (DENZO; Otwinowski & Minor, 1997) T_min = 0.972, T_max = 0.979
6132 measured reflections
1761 independent reflections
1483 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.107
S = 1.04
1761 reflections
113 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.24 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1ON2ⁱ	0.92 (2)	1.88 (2)	2.7919 (14)	169.8 (18)
N2-H2NO1ⁱⁱ	0.916 (18)	2.165 (18)	3.0790 (13)	175.7 (15)
N2-H2MN1ⁱⁱⁱ	0.929 (19)	2.525 (19)	3.3000 (14)	141.0 (14)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2552 ).

Acknowledgements

The authors gratefully acknowledge funds from the Higher Education Commission, Islamabad, Pakistan.

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.
Bertolasi, V., Gilli, G. & Veronese, A. C. (1982). Acta Cryst. B38, 502-511.
Brandenburg, K. (2007). DIAMOND. Crystal Impact Gbr, Bonn, Germany.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.
Degorre, F., Kiffer, D. & Terrie, F. (1998). J. Med. Chem. 31, 757-761.
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzimology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds