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J Chem Crystallogr (2010) 40:376–380
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References
Table 3 Hydrogen bonding geometry (A, °) for 3-(4-(phenylami-
no)phenylamino) cyclohex-2-enone
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D–HÁÁÁA
D–H
DÁÁÁA
HÁÁÁA
D–HÁÁÁA
C11–H11ÁÁÁO(1)
N2-H2 NÁÁÁO(1)
N1–H1 NÁÁÁO(2)
0.93(2)
0.89(2)
0.91(2)
3.358(2)
2.942(3)
2.846(2)
2.655(1)
2.122(27)
1.954(22)
132.9(1)
151.7(19)
165.3(2)
Symmetry codes: (1) -x ? 1, ?y ? 1/2, -z ? 1/2 ? 1; (2) x,
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properties in the crystal structure such as molecular cis-
keto form [31]. In the molecular structure, the C–O bond
length is the most sensitive indicator of the type of tauto-
meric form. It is a single bond in the case of the enol-imino
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˚
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bond length of the title compound, which is slightly longer
˚
than the expected value of 1.222 A for a double bond [32].
According to the enol form and electron delocalizations
some bond lengths can be deviated from the expected
values [32]. In molecular structures of acyclic b-enami-
nones, conformational isomerism is usually expected,
however, the title compound has a cyclic structure and
shows only E isomer. In conjunction with literature data
reported for compounds containing the b-enaminone
structure the conformation of enaminone can be deduced
from their 1H and 13C NMR data [25, 26]. The newly
prepared b-enaminone compound, owing to the influence
of strong intermolecular hydrogen bonding, exists only as
the E-s-E-s-Z conformation (Scheme 1). This is consistent
with X-ray crystallographic study.
In summary, the X-ray studies confirm the original
structural assignments based on spectroscopic techniques
and furthermore yield accurate structural parameters which
are useful for future biological and pharmaceutical mod-
eling studies.
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Supplementary Data
CCDC-657271 contains the supplementary crystallo-
graphic data for the compound reported in this paper.
These data can be obtained free of charge at http://www.
bridge Crystallographic Data Centre (CCDC), 12 Union
Road, Cambridge CB2 1EZ, UK; fax: ?44-1223-336033;
e-mail: deposit@ccdc.cam.ac.uk].
´
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Acknowledgments This work was supported financially by Hacet-
tepe University (Research Center Office/Projects No: 01.02.602.002
and 05A601009).
123