FORMATION OF ONE-DIMENSIONAL CHAINS, 2-DIMENSIONAL BILAYERS AND A 3-DIMENSIONAL DIAMONDOID ARCHITECTURE IN HYDROGEN-BONDED ADDUCTS OF 4,4'-BIPHENOL WITH 1,4-DIAZABICYCLO[2.2.2]OCTANE AND 1,2-DIAMINOETHANE
G. Ferguson et al., FORMATION OF ONE-DIMENSIONAL CHAINS, 2-DIMENSIONAL BILAYERS AND A 3-DIMENSIONAL DIAMONDOID ARCHITECTURE IN HYDROGEN-BONDED ADDUCTS OF 4,4'-BIPHENOL WITH 1,4-DIAZABICYCLO[2.2.2]OCTANE AND 1,2-DIAMINOETHANE, Acta crystallographica. Section B, Structural science, 54, 1998, pp. 151-161
In 4,4'-biphenol-1,4-diazabicyclo[2.2.2]oct (1/1), C12H10O2 .C6H12N2 (
1), monoclinic, C2/c, a = 12.1510(9), b = 6.3202(4), c = 21.051(2)Angs
trom, beta = 98.875 (10)degrees with Z = 4, the biphenol units lie acr
oss twofold rotation axes and the diamine units are disordered across
centres of inversion. The molecular components are linked by means of
O-H ... N hydrogen bonds into zigzag chains with graph set C-2(2)(16)
running parallel to the [201] direction; the chains are not coiled and
there are no interactions between neighbouring chains. In 4,4'-biphen
ol-1,2-diamino-ethane-methanol (2/1/1), (C12H10O2)(2 .)C2H8N2 .CH4O (2
), triclinic, P (1) over bar, a = 9.4592 (7), b = 10.6311(10), c 12.20
85 (14) Angstrom, alpha = 91.812(9), beta = 93.091(6), gamma = 90.652(
6)degrees with Z = 2, there are seven independent hydrogen bonds of O-
H ... O, O-H ... N and N-H ... O types and each oxygen and each nitrog
en acts as a single donor and single acceptor of hydrogen bonds. The f
our independent components are linked by means of O-H ... O and O-H ..
. N hydrogen bonds into a linear aggregate, and further O-H ... N and
O-H ... O hydrogen bonds generate chains in the [011] direction contai
ning alternating biphenol and diamine units, and in the [021] directio
n containing methanol and pairs of biphenol molecules. These two types
of chain intersect to form a continuous two-dimensional net, graph se
t R-10(10)(62), with biphenol molecules at the nodes: pairs of these n
ets are linked into bilayers by N-H ... O hydrogen bonds, but the nets
are not interwoven. In 4,4'-biphenol-1,2-diaminoethane (1/1), C12H10O
2 .-C2H8N2 (3), monoclinic, P2(1)/a, a = 8.2121(5), b= 5.3401 (3), c =
14.6014 (9) Angstrom, beta= 99.962 (7)degrees with Z = 2, each of the
components lies across a centre of inversion. The O atoms act as sing
le donors and double accepters of hydrogen bonds and the N atoms as do
uble donors and single accepters, so that both oxygen and nitrogen are
effectively four-coordinate; all the hydrogen bonds are of O-H ... N
or N-H ... O type. Chains built from N-H ... O and O-H ... N hydrogen
bonds run parallel to [100] and [010] and the intersection of these gi
ves two-dimensional nets built from R-6(6)(12) rings: these nets are l
inked by the -C6H4C6H4- and -CH2CH2-spacer units into a continuous thr
ee-dimensional diamondoid structure.