organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
ISSN 0108-2701
(E)-1-(2-Hydroxyphenyl)propan-2-one
O-methyloxime forms hydrogen-
bonded chains of edge-fused R44(16)
and R44(24) rings
Christopher Glidewell,a* John N. Low,b
Janet M. S. Skakleb and James L. Wardellc
aSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland,
bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen
Figure 1
c
The two independent molecules in compound (I), showing the atom-
labelling scheme. Displacement ellipsoids are drawn at the 30%
probability level and H atoms are shown as small spheres of arbitrary
radii.
Â
Â
AB24 3UE, Scotland, and Instituto de Quõmica, Departamento de Quõmica
Ã
Inorganica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ,
Brazil
Correspondence e-mail: cg@st-andrews.ac.uk
Received 13 February 2004
Accepted 17 February 2004
Online 11 March 2004
The molecules of (I) are linked into a chain of edge-fused
rings by the combination of two nearly linear OÐHÁ Á ÁN
hydrogen bonds and one rather weak CÐHÁ Á ÁO hydrogen
bond (Table 2). Within the asymmetric unit, phenolic atom O1
in the type 1 molecule (containing O1, etc.) acts as hydrogen-
bond donor to oxime atom N28 in the type 2 molecule
(containing O2, etc.) (Fig. 1), and in a similar way, phenolic
atom O2 in the type 2 molecule at (x, y, z) acts as hydrogen-
bond donor to oxime atom N18 in the type 1 molecule at (x, y,
The title compound, C10H13NO2, crystallizes with Z0 = 2 in
space group P1. The molecules are linked by two OÐHÁ Á ÁN
Ê
hydrogen bonds [HÁ Á ÁO = 1.97 and 1.98 A, OÁ Á ÁN = 2.810 (2)
ꢀ
Ê
Ê
and 2.815 (2) A, and OÐHÁ Á ÁN = 175 and 174 ] and by one
CÐHÁ Á ÁO hydrogen bond [HÁ Á ÁO = 2.50 A, CÁ Á ÁO =
ꢀ
Ê
3.313 (2) A and CÐHÁ Á ÁO = 144 ] into chains of edge-fused
centrosymmetric rings in which R44(16) and R44(24) rings
alternate.
z
1). The combination of these two hydrogen bonds then
generates by translation a C22(14) (Bernstein et al., 1995) chain
running parallel to the [001] direction (Fig. 2).
Two such chains, related to one another by inversion, pass
through each unit cell, and these two chains are weakly linked
by the CÐHÁ Á ÁO hydrogen bond. Aryl atom C23 in the type 2
molecule at (x, y, z) acts as hydrogen-bond donor to phenolic
atom O1 in the type 1 molecule at (1 x, 1 y, 1 z), so
Comment
The title compound, (I), was originally prepared as part of a
study of the cyclization reactions of phenolic oximes
(Forrester et al., 1975). Its structure has now been determined
in order to establish both the geometry at the oxime group and
the nature of the supramolecular interactions.
Compound (I) crystallizes in space group P1, with two
independent molecules in the asymmetric unit (Fig. 1). Both
molecules have the E con®guration at the C N bond. The
intramolecular dimensions are very similar in the two mol-
ecules, and the bond distances show no unusual features. The
angles at the planar C atoms C18 and C28 show considerable
variation from 120ꢀ (Table 1) and both of the CÐNÐO angles
are substantially less than 120ꢀ. As shown by the leading
torsion angles, the conformations of the two molecules are
very similar.
Figure 2
Part of the crystal structure of (I), showing the formation of a C22(14)
chain along [001]. For the sake of clarity, H atoms bonded to C atoms
have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at
the symmetry positions (x, y, z 1) and (x, y, 1 + z), respectively.
Acta Cryst. (2004). C60, o245±o247
DOI: 10.1107/S0108270104003737
# 2004 International Union of Crystallography o245
Glidewell, Christopher
