Hydrogen-bonded molecular ladders and interlaced networks in complexes built of V-shaped molecules 4,4′-isopropylidenediphenol or 4,4′-oxydibenzoic acid with 4,4′-bipyridine

Article abstract of DOI:10.1007/s10870-011-0020-z

The title compounds, C₁₀H₈N₂?C ₁₅H₁₆O₂ (1) and C₁₀H ₈N₂?C₁₄H₁₀O₅ (2), were synthesized by 4,4′-bipyridyl and two similar V-shaped molecules. The two complexes both crystallized in the same space group P2₁/n with the crystal cell parameters: a = 16.0536(3) A, b = 6.42730(1) A, c = 21.2717(4) A, β = 102.330°, V = 2144.21(7) A³, Z = 4 in compound 1 and a = 7.45020(10) A, b = 10.0784(2) A, c = 26.9430(5) A, β = 92.1140(10)°, V = 2021.67(6) A³, Z = 4 in compound 2. Compound 1 forms regular molecular chains containing alternative 4,4′-bipyridyl and 4,4′- isopropylidenediphenol units; the molecular components are linked by two types of O-H???N hydrogen bonds. Additionally, every two neighboring chains are connected to be a ladder structure by means of weak C-H???O interactions. In compound 2, 4,4′-bipyridyl and 4,4′-oxydibenzoic acid first construct one-dimensional architecture by strong O-H???N hydrogen bonds, which are similar with the interactions in compound 1. Secondly, two types of weak C-H???O contacts formed between 4,4′-bipyridyl and the acid link one-dimensional chains to be interlaced three-dimensional hydrogen-bonded networks.

Full text of DOI:10.1007/s10870-011-0020-z

J Chem Crystallogr (2011) 41:929–935
DOI 10.1007/s10870-011-0020-z
ORIGINAL PAPER
Hydrogen-Bonded Molecular Ladders and Interlaced Networks
in Complexes Built of V-Shaped Molecules 4,40-
Isopropylidenediphenol or 4,40-Oxydibenzoic Acid
with 4,40-Bipyridine
•
Yunxia Yang Qi Li
Received: 9 December 2010 / Accepted: 1 February 2011 / Published online: 10 February 2011
Ó Springer Science+Business Media, LLC 2011
Abstract The title compounds, C10H8N2ꢀC15H16O2 (1)
and C10H8N2ꢀC14H10O5 (2), were synthesized by 4,40-
bipyridyl and two similar V-shaped molecules. The two
complexes both crystallized in the same space group P21/
Keywords 4,40-Bipyridyl ꢀ 4,40-Isopropylidenediphenol ꢀ
4,40-Oxydibenzoic acid ꢀ Hydrogen bond ꢀ Cocrystal
˚
n with the crystal cell parameters: a = 16.0536(3) A, b =
Introduction
˚
˚
6.42730(1) A, c = 21.2717(4) A, b = 102.330°, V =
3
2144.21(7) A , Z = 4 in compound 1 and a = 7.45020(10) A,
˚
˚
Cocrystal formation is of high effectiveness in construction
of organic solid-state materials that exhibit customized
properties (e.g., optical, photo, electrical, mechanical,
pharmaceutical property) [1–8]. Recognizing that crystal
engineering is the solid-state supramolecular equivalent of
organic synthesis, supramolecular synthons are ‘structural
units within supermolecules formed and/or assembled by
known or conceivable intermolecular interactions’.
The O–HꢀꢀꢀN hydrogen bond is a robust and versatile
synthon in terms of crystal engineering [9–11]. The bis-
phenolic compound, 4,40-isopropylidenediphenol, which
has been widely used in many areas including biochemistry
[12–15] and environmental chemistry [16, 17], could form
several adducts with different amines, e.g., 1,4-diazabicy-
clo[2.2.2]octane [18], hexamethyltetramine [19], meth-
ylhydrazine [20], quinoline [21] and pyridine [22]. Among
these structures, it is obvious that the bisphenol is a good
double hydrogen-bond donor resembling V-shape. Simi-
larly, 4,40-oxydibenzoic acid, which is generally employed
to construct different MOFs [23–27], also exists as an
analogical V-configuration molecule with terminal car-
boxyl groups acting as good hydrogen-bond acceptors and
donors. It is well known that 4,40-bipyridyl is a double
hydrogen-bond acceptor. 4,40-isopropylidenediphenol and
4,40-oxydibenzoic acid molecules both display in the con-
figuration of V-shape, but the terminal functional groups
are very different.
˚
˚
b = 10.0784(2) A, c = 26.9430(5) A, b = 92.1140(10)°,
3
V = 2021.67(6) A , Z = 4 in compound 2. Compound
˚
1 forms regular molecular chains containing alternative
4,40-bipyridyl and 4,40-isopropylidenediphenol units; the
molecular components are linked by two types of O–HꢀꢀꢀN
hydrogen bonds. Additionally, every two neighboring
chains are connected to be a ladder structure by means of
weak C–HꢀꢀꢀO interactions. In compound 2, 4,40-bipyridyl
and 4,40-oxydibenzoic acid first construct one-dimensional
architecture by strong O–HꢀꢀꢀN hydrogen bonds, which are
similar with the interactions in compound 1. Secondly, two
types of weak C–HꢀꢀꢀO contacts formed between 4,40-
bipyridyl and the acid link one-dimensional chains to be
interlaced three-dimensional hydrogen-bonded networks.
Y. Yang ꢀ Q. Li (&)
College of Chemistry, Beijing Normal University,
Beijing 100875, China
e-mail: qili@bnu.edu.cn
Y. Yang
Key Laboratory of Eco-Environment-Related Polymer Materials,
Ministry of Education, College of Chemistry and Chemical
Engineering, Northwest Normal University, Lanzhou 730070,
Gansu, China
In recent years, multiple systematic studied on construc-
tion of new inclusion compounds and the hydrogen-bonding
123

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J Chem Crystallogr (2011) 41:929–935
modes within their crystal structures were undertaken by
our researchers. A number of novel inclusion compounds
have been synthesized based on multi-carboxylato ali-
phatic or aromatic rings, with or without participation of
urea or thiourea molecules [28]. As a part of our ongoing
investigation on properties and molecular packing of
inclusion compounds based on multi-carboxylato aro-
matic rings, some new cocrystals have been prepared in
successive way. For ongoing work, preparation and X-ray
crystallographic analyses of two complexes, 4,40-bip-
yridylꢀ4,40-isopropylidenediphenol (1) and 4,40-bipyri-
dylꢀ4,40-oxydibenzoic acid (2) were reported in this
paper.
Table 1 Crystallographic data
Formula
C10H8N2ꢀC15H16O2 C10H8N2ꢀC14H10O5
Formula weight
Crystal color
Crystal shape
Crystal system
Space group
Crystal size/mm
384.46
414.40
Colorless
Prism
Colorless
Prism
Monoclinic
P21/n
Monoclinic
P21/n
0.68 9 0.48 9 0.53 0.60 9 0.27 9 0.21
˚
a/A
16.0536(3)
6.42730(1)
21.2717(4)
102.330
2144.21(7)
4
7.45020(10)
10.0784(2)
26.9430(5)
92.1140(10)
2021.67(6)
4
˚
b/A
˚
c/A
b/°
3
˚
V/A
Z
Dc/(mg cm-3
l/mm-1
)
1.191
1.362
Experiment
0.076
0.097
Synthesis of 4,40-Bipyridylꢀ4,40-isopropylidenediphenol
(C10H8N2ꢀC15H16O2, 1) and 4,40-Bipyridylꢀ4,40-
oxydibenzoic acid (C10H8N2ꢀC14H10O5, 2)
h range for data collection 1.79–27.62
2.52–27.65
9645
Reflection number
Independent reflections
R1,wR2[I [ 2r(I)]
R1,wR2(all data)
S
13355
4972
4687
0.0462, 0.1267
0.0621, 0.1420
1.041
0.0430, 0.1165
0.0607, 0.1300
1.025
0.25 mmol 4,40-bipyridyl (0.039 g) and 0.25 mmol 4,40-
isopropylidenediphenol (0.057 g) were separately dis-
solved in a small amount of water–ethanol (50/50 v/v). The
mixture were stirred for half an hour and set aside to
crystallize, after 7 days, finally yielding colorless prism-
shaped crystals suitable for single crystal X-ray diffraction.
Compound 2 was prepared with the same procedure with
0.25 mmol 4,40-oxydibenzoic acid (0.065 g), and the
resulting solution was set aside and allowed to slowly
evaporate at room temperature. After 7 days, colorless
prism-shaped crystals of compound 2 suitable for single
crystal X-ray diffraction were obtained.
Results
Crystal Structure of 4,40-Bipyridyl-4,40-
isopropylidenediphenol (1)
Compound 1 crystallizes in P21/n with one molecule of
bipyridyl and one molecule of bisphenol lying in the gen-
eral positions, thus giving a 1:1 molar ratio of bipyridyl to
bisphenol, and it is explicitly observed that the hydroxyl
hydrogen atoms are fully ordered and there is no evidence
for any proton transfer from bisphenol to pyridyl (Fig. 1a).
Within the asymmetric unit, the oxygen atoms of bisphe-
nol, O1 and O2, both act as hydrogen-bond donors to
interact with the nitrogen atoms N1 and N2 belonged to
bipyridyl, which form two types of O–HꢀꢀꢀN hydrogen
bonds (Fig. 2a). The O–HꢀꢀꢀN interactions between two
components give an infinite molecular chain along the
[101] orientation, and these chains translated by n glide
plane are regularly arranged in b axis (Fig. 2a). Notably,
thinking of weak C–HꢀꢀꢀO hydrogen bond formed between
carbon atom C7 of bipyridyl and hydroxyl oxygen atom O1
of bisphenol (Figs. 1a, 2b) as the rungs of the ladder
structure, two neighboring molecular chains related by 21
screw axis are connected to be the molecular ladder
stretching toward the [101] orientation, and the bordering
X-ray data Collection and Structure Determination
Crystals were mounted on glass fibers for intensity data
collection with a Bruker SMART Apex II CCD area
detector [29] at room temperature. All data were collected
using graphite-monochromated Mo–Ka radiation (k =
˚
0.71073 A). The structure was solved with direct methods
and refined by full matrix least square methods based on
F2, using the structure determination and graphics package
SHELXTL based on SHELX97 [30]. All non-hydrogen
atoms were refined with anisotropic displacement param-
eters, and all the hydrogen atoms bonded to carbon atoms
were introduced into idealized dispositions. The hydrogen
atoms bonded to oxygen atoms were placed in difference
˚
map with fixed distance of 0.86 A. The final reliability
indices together with crystal data of the refinement
calculations were given in Table 1 and the selected geo-
metric parameters of two crystal structures were listed in
Table 2.
ꢀ
ladders are arranged in the direction ½101ꢁto acquire final
three-dimensional crystal structure (Fig. 2b).
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J Chem Crystallogr (2011) 41:929–935
931
˚
Table 2 Selected geometric parameters (fl. A)
˚
Table 2 Selected geometric parameters (fl. A)
1
Bond angle
Bond distance
C(1)–N(1)
C(21)–O(1)–C(14)
C(5)–N(1)–C(1)
C(10)–N(2)–C(6)
C(2)–C(3)–C(8)
C(4)–C(3)–C(8)
C(9)–C(8)–C(3)
C(7)–C(8)–C(3)
N(1)–C(5)–C(4)
N(2)–C(10)–C(9)
N(1)–C(1)–C(2)
N(2)–C(6)–C(7)
C(15)–C(14)–O(1)
C(13)–C(14)–O(1)
O(1)–C(21)–C(22)
O(1)–C(21)–C(20)
O(2)–C(17)–O(3)
O(2)–C(17)–C(11)
O(3)–C(17)–C(11)
O(5)–C(24)–O(4)
O(5)–C(24)–C(18)
O(4)–C(24)–C(18)
120.39(10)
117.13(12)
117.07(13)
121.17(13)
121.41(12)
120.61(13)
121.47(13)
123.48(13)
123.60(15)
123.45(14)
123.73(17)
117.14(13)
120.82(12)
125.05(11)
114.37(12)
123.76(12)
122.74(13)
113.48(11)
123.15(13)
123.61(13)
113.23(13)
1.327(2)
1.484(2)
1.316(2)
1.325(2)
1.329(2)
1.3609(2)
1.5351(2)
1.5311(2)
1.5363(2)
1.5380(2)
C(3)–C(6)
C(5)–N(1)
C(8)–N(2)
C(9)–N(2)
C(11)–O(1)
C(14)–C(17)
C(17)–C(18)
C(17)–C(24)
C(17)–C(25)
Bond angle
N(1)–C(1)–C(2)
C(2)–C(3)–C(6)
C(4)–C(3)–C(6)
N(1)–C(5)–C(4)
C(10)–C(6)–C(3)
C(7)–C(6)–C(3)
N(2)–C(8)–C(7)
N(2)–C(9)–C(10)
O(1)–C(11)–C(16)
O(1)–C(11)–C(12)
C(15)–C(14)–C(17)
C(13)–C(14)–C(17)
C(18)–C(17)–C(14)
C(18)–C(17)–C(24)
C(14)–C(17)–C(24)
C(18)–C(17)–C(25)
C(14)–C(17)–C(25)
C(24)–C(17)–C(25)
O(2)–C(21)–C(20)
O(2)–C(21)–C(22)
2
123.91(16)
122.64(12)
121.33(14)
124.36(16)
122.05(12)
121.89(13)
124.22(14)
123.28(14)
118.37(13)
123.31(13)
123.88(11)
120.11(11)
109.33(10)
112.23(10)
108.29(11)
107.54(11)
112.02(11)
107.47(12)
118.55(13)
123.09(13)
Crystal Structure of 4,40-Bipyridyl-4,40-oxydibenzoic
acid (2)
Compound 2 exhibits the same space group of P21/n, and
the asymmetric unit is constituted by one molecule of
bipyridyl and one molecule of oxydibenzoic acid in
general positions. Similarly, hydroxyl hydrogen atoms of
the acid are fully ordered and there is no proton transfer
from acid to pyridyl (Fig. 1b). Seen from Fig. 3a, the
hydroxyl oxygen atoms in carboxyl groups of 4,40-oxy-
dibenzoic acid, O3 and O4, separately interact with
nitrogen atoms N1 and N2 of bipyridyl to form one-
dimensional chains by using two conventional O–HꢀꢀꢀN
hydrogen bonds that are similar with the hydrogen
bonding in compound 1. Interestingly, the chains extend
to become two-dimensional layers along a axis generated
from the linkage of C–HꢀꢀꢀO hydrogen bonding between
carbon atom of bipyridyl and carbonyl oxygen atom
located in the acid, e.g., C9–H9AꢀꢀꢀO5B (Fig. 3a).
Moreover, another carbonyl oxygen atom O2 of 4,40-
oxydibenzoic acid is also able to generate C–HꢀꢀꢀO
hydrogen bond with the carbon atom adjacent to N1 atom
of pyridyl ring and this weak contact changes the forgo-
ing layers into three-dimensional interlaced hydrogen-
bonded networks shown in block diagram of compound 2
(Fig. 3b).
Bond distance
O(1)–C(21)
1.3726(15)
1.3948(15)
1.3153(17)
1.2075(16)
1.3158(18)
1.2052(18)
1.3249(19)
1.3275(19)
1.321(2)
O(1)–C(14)
O(3)–C(17)
O(2)–C(17)
O(4)–C(24)
O(5)–C(24)
N(1)–C(5)
N(1)–C(1)
N(2)–C(10)
N(2)–C(6)
1.333(2)
C(3)–C(8)
1.4882(17)
1.4948(17)
1.4880(18)
C(11)–C(17)
C(18)–C(24)
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(a)
(b)
Fig. 1 A view of the unique molecular components of compound 1 (a) and 2 (b). Displacement ellipsoids are drawn at 30% probability level
(b)
(a)
Fig. 2 a Part of the crystal structure of compound 1 showing the
infinite chains arranged in the b axis. [Symmetry codes: A 1/2 ? x,
-y ? 2/3, -1/2 ? z]. b Depiction of the 3-D nature of the hydrogen
bonding networks of compound 1 viewed down the b-axis, with
the a-axis pointing to the southwest direction. For the sake of clarity,
all the hydrogen atoms bond to carbon are omitted in a but the ones
that involve in the hydrogen bonds are signified in b
Discussion
In compounds 1 and 2, O–HꢀꢀꢀN hydrogen bonds and
weak C–HꢀꢀꢀO contacts are essential interactions to yield
ultimate crystal structures. Seen from Table 3, in com-
pound 1, the distance of OꢀꢀꢀN varies from 2.7424 to
Complex 1 forms regular molecular chains containing
alternative 4,40-bipyridyl and 4,40-isopropylidenediphenol
units which are linked with O–HꢀꢀꢀN hydrogen bonds.
Interestingly, every two neighboring chains are further
connected to be a ladder structure by weak C–HꢀꢀꢀO
interactions. Meanwhile, in compound 2, 4,40-bipyridyl and
4,40-oxydibenzoic acid form one-dimensional architec-
ture firstly; the molecular components are connected by
strong O–HꢀꢀꢀN contacts. Additionally, two kinds of weak
C–HꢀꢀꢀO hydrogen bonds formed between 4,40-bipyridyl
and the acid link one-dimensional chains to be interlaced
three-dimensional hydrogen-bonded networks. Obviously,
the conventional O–HꢀꢀꢀN hydrogen bonds play a signifi-
cant role in the formation of two cocrystals, but to some
extent, weak C–HꢀꢀꢀO interaction causes distinction to exist
between these two crystal structures.
˚
2.7663 A, and angle of O–HꢀꢀꢀN from 170° to 171°,
whereas the corresponding distances from 2.6718 to
˚
2.6729 A, and the angles from 176° to 174° in compound
2. Apparently, the O–HꢀꢀꢀN hydrogen bonds of compound 2
are stronger than those in compound 1. Compared with the
related parameters of O–HꢀꢀꢀN hydrogen bonds formed by
V-shaped analogues and bipyridyl as well as its derivatives
[31–34], the changes of the OꢀꢀꢀN distances and the cor-
responding angles of compound 1 and 2 are within the
range of relevant values (The distance of OꢀꢀꢀN varies from
˚
2.629 to 2.792 A and the angles from 162° to 176°). From
the two structures of this paper and other analogous
structures in the literatures, it can be speculated that
O–HꢀꢀꢀN hydrogen bond is a kind of efficient interaction to
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J Chem Crystallogr (2011) 41:929–935
933
(a)
(b)
Fig. 3 a Part of the crystal structure of compound 2 showing the two-
dimensional layer along the a-axis. [Symmetry codes: A 5/2 ? x,
-1 ? y, 1/2 ? z; B 3/2 ? x, -1 ? y, 1/2 ? z]. b Projection of the
3-D nature of the interlaced networks of 2 viewed down the a-axis.
All the hydrogen atoms but the ones that involve in the hydrogen
bonds are omitted for clarity in b
Table 3 Hydrogen bonding geometry
hydrogen bonds in these two cocrystals are comparable
˚
with normal values (3.35(2) A and 127(1)°) [36].
˚
Distance (A)
Hydrogen bond
Angle (°)
In crystal structure of compound 1, the dihedral angle
of two benzenes of 4,40-isopropylidenediphenol is 87.5°,
close to right-angle. Comparatively, the relevant angle of
4,40-oxydibenzoic acid is 66.6° in compound 2. Evidently,
the interplanar angle of 4,40-isopropylidenediphenol in
compound 1 is greater than 4,40-oxydibenzoic acid. That
is to say, the repulsion of unshared pair electrons belon-
ged to bridged oxygen atom of 4,40-oxydibenzoic acid is
not as strong as that yielded by two methyls in 4,40-iso-
propylidenediphenol. Thus 4,40-oxydibenzoic acid exhibits
a gentle V-shaped structure compared with 4,40-isopro-
pylidenediphenol. Analyzing the crystal structures of
4,40-sulfonyldiphenolꢀ4,40-bipyridyl (3) [34], 4,40-bipyri-
dylꢀ4,40-thiodiphnol (4) [32] and 4,40-dihydroxybenzo-
phenoneꢀ4,40-bipyridyl (5) [33], these three compounds
are all constructed by similar V-shaped molecules with
terminal hydroxyl groups and 4,40-bipyridyl, but the
central bridge atoms or groups of the V-shaped compo-
nents are very different. In compound 3, the dihedral
angle of two benzenes connected by O=S=O group is
88.8°, whereas in complexes 4 and 5, which are linked by
S atom and C=O group separately, the corresponding
values are 75.8° and 63.0°. Obviously, according to tor-
sion angles, the sequence should be 3 [ 1 [ 4 [ 2 [ 5.
That is to say, if it is expressed by the central bridge
atoms or groups, the order should be O=S=O [ Me–C–
Me [ S [ O [ C=O. Conclusion can be made that the
repulsions of O=S=O and Me–C–Me are similar and they
are both stronger than forces generated by unshared pair
electrons of single S or O atom. Regarding C=O group,
Compound 1
O1ꢀꢀꢀN1
2.7663
2.7424
3.3646
171
170
160
O2ꢀꢀꢀN2
C7ꢀꢀꢀO1
Compound 2
O3ꢀꢀꢀN1
2.6729
2.6718
3.2920
3.3290
174
176
155
145
O4ꢀꢀꢀN2
C2ꢀꢀꢀO2
C9ꢀꢀꢀO5
synthesize crystal structures. Thus it can be seen, it is
useful to pre-design some interesting structures if the
linkage models of different hydrogen bonds can be
obtained.
Although two structures mentioned above form one-
dimensional architecture by O–HꢀꢀꢀN hydrogen bonds, the
final packing modes of two compounds are not identical for
the influence of weak C–HꢀꢀꢀO interactions. There is only
one type of weak C–HꢀꢀꢀO hydrogen bond in compound 1,
˚
in which the related distance reaches 3.3646 A and the
angle 160°, whereas there exist two C–HꢀꢀꢀO hydrogen
bonds in compound 2 (The corresponding distances are
˚
3.2920 and 3.3290 A, and the angles 155° and 145°).
C–HꢀꢀꢀO contact is not a classic hydrogen bond, but many
properties of C–HꢀꢀꢀO interaction have been discussed
because weak and less common types of hydrogen bonds
have been major topics in hydrogen bond research [35, 36].
Obviously, the related distances and angles of C–HꢀꢀꢀO
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J Chem Crystallogr (2011) 41:929–935
V-shaped molecule having a smaller torsion angle com-
pared with other analogues in compound 5 is possibly due
to its planarity .
unit cell volume, and the percent of filled space of com-
pound 2 realizes 68.4% and the unit cell contains no
residual solvent accessible void. Clearly, the V-shaped
molecules and 4,40-bipyridyl pack so tightly that no guest
molecules can be included within them.
Meanwhile, it can be found that the dihedral angle of
two pyridyls is 19.3° in compound 1 and 37.5° in 2. Cal-
culating the optimized configuration of a single 4,40-
bipyridyl molecule using the Hartree–Fock method based
on the 3-21G basis set by the program Gaussian03 W [37],
the result shows that the dihedral angle of two pyridyl rings
is up to 49.2°. In other words, 4,40-bipyridyl distorts to
greater extent in compound 1 compared with optimized
structure of itself. In compounds 3, 4 and 5, the V-shaped
molecules all have terminal hydroxyl groups and the cor-
responding angles of bipyridyls are 24.4°, 25.8° and 12.7°,
compared with the related values in compound 1. As we
have calculated the relevant interplanar angles of the
V-shaped molecules in those five cocrystals, it is evident
that the configuration of 4,40-oxydibenzoic acid in com-
pound 2 is comparatively gentle and its terminal carboxyl
groups can subtly adjust their torsion angles (The dihedral
angles between the carboxyl groups and the related ben-
zene rings amount to 5.8° and 7.3°) to access pyridyl rings
of 4,40-bipyridyl. Thus 4,40-bipyridyl of 2 doesn’t need too
much distortion to match 4,40-oxydibenzoic acid. On the
contrary, in complexes 1, 3, 4 and 5, the terminal groups of
the V-shaped components are all hydroxyl groups rotating
along single C–O bond. To adapt the configuration of
bisphenol and to generate hydrogen bonds as many as
possible, 4,40-bipyridyl in these four compounds contorts at
least 23° from its optimized structure, thus builds final
crystal structures.
Supplementary Materials
CCDC 710200 and 747454 contain the supplementary
crystallographic data for this paper. These data can be
obtained free of charge via www.ccdc.cam.ac.uk/data
request/cif, by e-mailing data request@ccdc.cam.ac.uk, or
by contracting the Cambridge Crystallographic Data Cen-
tre, 12 Union Road, Cambridge CB2 1EZ, UK; fax:
?44(0)1223-336033.
Acknowledgments Support from the National Nature Science
Foundation of China (Grant No. 20871019) is gratefully acknowl-
edged.
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