organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
HÁ Á ÁO hydrogen bonds (Table 2). Hydroxy atom O1 acts as a
1
2
1
2
hydrogen-bond donor to atom O2 at (x � , y � , z), thus
generating chains of molecules running parallel to [110], and
atom O3 acts as a hydrogen-bond donor to atom O1 at (1 + x,
y, 1 + z), thus generating chains of molecules parallel to [101].
The intersection of these two linear motifs generates two-
dimensional square networks parallel to the (111) plane
ISSN 0108-2701
Hydrogen-bond networks in
tris(4-hydroxyphenyl)methane
and its 1:1 molecular complex
(
Fig. 2), which are identical to the square nets observed in
the crystal structure of 1,1,1-tris(4-hydroxyphenyl)ethane
Ferguson et al., 1997), with which the present compound is
isomorphous [after appropriate cell transformation of the
,1,1-tris(4-hydroxyphenyl)ethane cell from Ia to Cc]. The
third hydroxy group (O2) acts as a hydrogen-bond donor to
(
0
with 4,4 -bipyridine
1
a
a
Srinivasulu Aitipamula, Ashwini Nangia, *
1
1
3
atom O3 at (x � , � y, z � ), thus generating an identical
b
b
2
2
2
Ram Thaimattam and Mariusz Jask o lski
square network parallel to the (111) plane. These two square
ꢁ
networks interpenetrate in the structure at an angle of ꢀ160 ,
a
School of Chemistry, University of Hyderabad, Hyderabad 500 046, India, and
b
being connected via the O2ÐH2Á Á ÁO3 hydrogen bond (Fig. 3).
Centre for Biocrystallographic Research, IBCh, Polish Academy of Sciences, and
Department of Crystallography, Mickiewicz University, Grunwaldzka 6, 60-780
Poznan, Poland
Received 18 June 2003
Accepted 25 June 2003
Online 31 July 2003
0
00
In tris(4-hydroxyphenyl)methane (or 4,4 ,4 -methanetriyltri-
phenol), C H O , molecules are connected by OÐHÁ Á ÁO
1
9
16
3
Ê
hydrogen bonds [OÁ Á ÁO = 2.662 (2) and 2.648 (2) A] into two-
dimensional square networks that are twofold interpene-
0
trated. In tris(4-hydroxyphenyl)methane±4,4 -bipyridine (1/1),
C H O ÁC H N , trisphenol molecules form rectangular
1
9
16
3
10
8
2
Ê
The crystal structure of (II) contains one molecule of (I)
0
networks via OÐHÁ Á ÁO [OÁ Á ÁO = 2.694 (3) A] and CÐHÁ Á Á
Ê
and one molecule of 4,4 -bipyridine in the asymmetric unit
(Fig. 4). One of the hydroxy groups of the molecule of (I) acts
as a hydrogen-bond donor to a d-glide-related O atom, and
O [CÁ Á ÁO = 3.384 (3) A] hydrogen bonds. Bipyridine mol-
ecules hydrogen bonded to phenol moieties [OÁ Á ÁN =
Ê
.622 (3) and 2.764 (3) A] ®ll the voids to complete the
2
structure.
the other two hydroxy groups act as hydrogen-bond donors to
0
4
,4 -bipyridine molecules. Each molecule of (I) is connected to
Comment
The crystal structures of 1,1,1-tris(4-hydroxyphenyl)ethane
and its adducts with many nitrogen bases have been reported
(
2
Ferguson et al., 1997; B e nyei et al., 1998; Zakaria et al.,
002a,b). These structures contain sheets and open networks
+
�
of OÐHÁ Á ÁO, OÐHÁ Á ÁN and N ÐHÁ Á ÁO hydrogen bonds,
with up to tenfold interpenetration of giant hexagons in 1,1,1-
0
tris(4-hydroxyphenyl)ethane±4,4 -bipyridine (2/3) (B e nyei et
al., 1998). Molecules with C symmetry are important in the
3
crystal engineering (Desiraju, 1989; Moberg, 1998) of
supramolecular architectures, in host±guest systems and in the
design of non-linear optical materials. In this context, we have
determined the crystal structure of tris(4-hydroxyphenyl)-
0
methane, (I). Cocrystallization of (I) with 4,4 -bipyridine in a
2
:3 stoichiometry gave the 1:1 adduct, (II).
The crystal structure of (I) contains one molecule of tris(4-
hydroxyphenyl)methane in the asymmetric unit (Fig. 1). The
phenol groups act as donors and acceptors of hydrogen bonds,
such that each molecule is bonded to six others through OÐ
Figure 1
A view of the molecule of (I), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 50% probability level for non-H
atoms.
Acta Cryst. (2003). C59, o481±o484
DOI: 10.1107/S0108270103014288
# 2003 International Union of Crystallography o481