organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
ISSN 0108-2701
Racemic (1,4-dioxan-2-yl)diphenyl-
methanol
Tomi Hsiao, Robert M. Buchanan and Mark S. Mashuta*
Department of Chemistry, University of Louisville, Louisville, KY 40292, USA
Correspondence e-mail: msmashuta.xray@louisville.edu
Received 11 February 2011
Accepted 5 March 2011
Online 11 March 2011
Figure 1
A view of the S enantiomer of (I), showing 50% probability displacement
ellipsoids.
The title compound, C17H18O3, prepared by microwave
irradiation of benzophenone and dioxane, crystallizes in a
racemic mixture that forms one-dimensional chains via strong
hydrogen bonding of the hydroxy group to the adjacent
symmetry-generated 1,4-dioxan-2-yl group; the O—Hꢀ ꢀ ꢀO
crystallizes with one molecule in the asymmetric unit in the
noncentrosymmetric space group Cc, which was confirmed
using the program PLATON (routines ADDSYM and
NEWSYM; Spek, 2009). Two enantiomeric forms are present
and the structure of the S form is shown in Fig. 1. The Hooft
analysis parameters P2(true) = 1.000, P3(true) = 1.000,
P3(false) = 0.000 and Hooft y = 0.14 (7) obtained from
PLATON were used to assign the absolute configuration
(Hooft et al., 2008).
The C—C and C—O bond distances and associated bond
angles around atoms C1 [average = 109.04 (17)ꢁ] and C2
[average = 109.48 (14)ꢁ] are consistent with sp3 hybridization
(Table 1). The C—C and C—O distances, and respective
angles, for the phenyl and dioxanyl groups are normal. The
phenyl rings adopt a twisted arrangement, minimizing ring-to-
ring and Hꢀ ꢀ ꢀH atom interactions, while the dioxanyl group
adopts a distorted-chair conformation.
ꢁ
˚
distance is 1.99 (3) A and the O—Hꢀ ꢀ ꢀO angle is 160 (2) .
Comment
The formation of C—C bonds is an important synthetic step in
organic synthesis, and there are several well known methods
that efficiently promote this bond-formation process. One
frequently used method involves the coupling of carbon
radicals generated during photolysis (Ohkura et al., 2004;
Derk et al., 2008), radiolysis (Burr & Strong, 1959), oxidation
reactions (Beccalli et al., 2007; Yu et al., 2009) and organo-
metallic catalysed reactions (Hartwig, 2008). The known title
compound, (I), was synthesized using microwave irradiation to
promote C—C bond coupling between dioxane and benzo-
phenone, and was isolated as a racemic mixture upon crys-
tallization. (I) has been prepared previously by UV irradiation
1
of benzophenone in dioxane, and characterized by H and
13C NMR and mass spectrometry (Bakar Bin Baba et al., 1985;
Droste et al., 1969). However, to date, no crystal structure of
(I) has been reported.
Figure 2
A packing diagram for (I), showing the intermolecular hydrogen-bonding
The C—C bond coupling between the 2-position C atom of
dioxane and the carbonyl C atom of benzophenone results in
the formation of a stereocenter at atom C2. Compound (I)
interactions between atoms H30A and O2i of adjacent S and R
1
2
enantiomers. [Symmetry code: (i) x, ꢂy + 1, z ꢂ .]
Acta Cryst. (2011). C67, o129–o130
doi:10.1107/S0108270111008419
# 2011 International Union of Crystallography o129
Hsiao, Tomi
