Catena-Poly[[[(di-2-pyridylamineκ2N2,N 2′)copper(II)]-μ-benzene-1,3-dicarboxylato-κ3O 1,O1′:O3] monohydrate], a zigzag coordination polymer with strong π-π Interactions

Article abstract of DOI:10.1107/S0108270111022451

The novel title coordination polymer, {[Cu(C₈H₄O ₄)(C₁₀H₉N₃)]·H ₂O}_n, synthesized by the slow-diffusion method, takes the form of one-dimensional zigzag chains built up of Cu^II cations linked by benzene-1,3-dicarboxyl-ate (ipht) anions. An exceptional characteristic of this structure is that it belongs to a small group of metal-organic polymers where ipht is coordinated as a bridging tridentate ligand with monodentate and chelate coordination of individual carboxyl-ate groups. The Cu^II cation has a highly distorted square-pyramidal geometry formed by three O atoms from two ipht anions and two N atoms from a di-2-pyridyl-amine (dipya) ligand. The zigzag chains, which run along the b axis, further construct a three-dimensional metal-organic framework via strong face-to-face π-π inter-actions and hydrogen bonds. A solvent water mol-ecule is linked to the different carboxyl-ate groups via hydrogen bonds. Thermogravimetric and differential scanning calorimetric analyses confirm the strong hydrogen bonding.

Full text of DOI:10.1107/S0108270111022451

metal-organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
phthalic) acid (H2ipht) combined with aromatic N-containing
chelating ligands have been used to assemble a wide range of
coordination polymers from chains to sheets to networks (see,
for example, Liu et al., 2008; Ma, Liu et al., 2010). The multi-
dimensional framework structures formed by these combina-
tions of aromatic ligands are often stabilized via noncovalent
intermolecular forces, viz. hydrogen bonds and/or ꢀ–ꢀ inter-
actions (Zhang et al., 2003; Li & Wei, 2007; An et al., 2008; Li et
al., 2009; Ma et al., 2009; Guo et al., 2010; He et al., 2010). The
title compound, {[Cu(ipht)(dipya)]ꢀH2O}n, (I), where dipya is
di-2-pyridylamine, represents a new example, comprising a
three-dimensional structure built up from one-dimensional
zigzag polymeric chains.
ISSN 0108-2701
catena-Poly[[[(di-2-pyridylamine-
0
j2N2,N2 )copper(II)]-l-0benzene-1,3-
dicarboxylato-j3O1,O1 :O3] mono-
hydrate], a zigzag coordination
polymer with strong p–p interactions
a
a
b
´
Jelena Rogan, * Dejan Poleti and Ljiljana Karanovic
aDepartment of General and Inorganic Chemistry, Faculty of Technology and
Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia, and
bLaboratory of Crystallography, Faculty of Mining and Geology, University of
ˇ
Belgrade, Ðusina 7, 11000 Belgrade, Serbia
Correspondence e-mail: rogan@tmf.bg.ac.rs
Received 6 May 2011
Accepted 9 June 2011
Online 17 June 2011
In (I), CuII cations are surrounded by three O atoms from
two carboxylate groups of neighbouring ipht anions and two N
atoms from dipya ligands, forming a (4+1) coordination
polyhedron, which can be described as a square pyramid with
a tetrahedrally distorted basal plane (Fig. 1). The dihedral
angle between coordinated carboxylate groups is 82.73 (8)ꢁ.
The bond distances between the CuII cation and atoms O1, O2
and O4 (Table 1) are within the usual ranges for complexes
where monodentate and chelate carboxylate groups of ipht or
substituted ipht are present (Li & Wei, 2007; Cui et al., 2009;
Du et al., 2009; Su et al., 2009; Zeng et al., 2009; Al-Hashemi et
al., 2010; Guo et al., 2010). The chelate O1—Cu1—O2 angle
[56.76 (6)ꢁ] is also similar to those found in these related
The novel title coordination polymer, {[Cu(C8H4O4)-
(C10H9N3)]ꢀH2O}n, synthesized by the slow-diffusion method,
takes the form of one-dimensional zigzag chains built up of
CuII cations linked by benzene-1,3-dicarboxylate (ipht)
anions. An exceptional characteristic of this structure is that
it belongs to a small group of metal–organic polymers where
ipht is coordinated as a bridging tridentate ligand with
monodentate and chelate coordination of individual carboxyl-
ate groups. The CuII cation has a highly distorted square-
pyramidal geometry formed by three O atoms from two ipht
anions and two N atoms from a di-2-pyridylamine (dipya)
ligand. The zigzag chains, which run along the b axis, further
construct a three-dimensional metal–organic framework via
strong face-to-face ꢀ–ꢀ interactions and hydrogen bonds. A
solvent water molecule is linked to the different carboxylate
groups via hydrogen bonds. Thermogravimetric and differ-
ential scanning calorimetric analyses confirm the strong
hydrogen bonding.
Comment
The design and synthesis of mixed metal–organic coordination
polymers are of current interest in the fields of supramolecular
chemistry and crystal engineering, not only for the fascinating
architectures and structural diversity of these compounds, but
also for their potential applications as functional materials (Li
& Wei, 2007; Cui et al., 2009; Du et al., 2009; Shyu et al., 2009;
Huang et al., 2010; Liu et al., 2010). An effective approach for
the synthesis of such complexes is the appropriate choice of
aromatic polycarboxylate ligands as bridges with a variety of
transition metal ions as nodes. During the past decade, there
have been many reports of the synthesis of coordination
compounds where dianions of benzene-1,3-dicarboxylic (iso-
Figure 1
Part of the polymeric zigzag chain of (I), showing the atom-numbering
scheme. Displacement ellipsoids are plotted at the 40% probability level.
1
1
2
1
2
1
2
1
2
[Symmetry codes: (i) ꢂx + , y ꢂ , ꢂz + 12; (ii) ꢂx + , y + , ꢂz + .]
2
m230 # 2011 International Union of Crystallography
doi:10.1107/S0108270111022451
Acta Cryst. (2011). C67, m230–m233

metal-organic compounds
Figure 2
The zigzag chain of (I), running along the b axis.
Figure 3
structures. Due to the constraints imposed by chelation, the
coordination polyhedron of Cu1 is highly distorted.
As expected, the apical Cu1—O2 bond distance
A projection of (I) along the b axis, showing the crystal packing, ꢀ–ꢀ
interactions and hydrogen bonding (dashed lines). For emphasis, solvent
water molecules are shown with displacement ellipsoids (orange in the
electronic version of the paper).
˚
[2.546 (2) A] is significantly longer than the remaining four
distances in the Cu1 coordination polyhedron (Table 1).
Nevertheless, according to bond-valence analysis (Wills, 2009),
atom Cu1 is oversaturated (2.21 bond valence units). A short
˚
(Guo et al., 2010) and 3.3 A (Zhang et al., 2003; Li et al., 2009)
were found, in most reported ipht and substituted ipht
complexes the ꢀ–ꢀ interactions are weaker and the distances
˚
are in the range 3.5–3.9 A (Zhang et al., 2003; Li & Wei, 2007;
i
1
˚
Cu1—O3 contact of 3.0229 (18) A [symmetry code: (i) ꢂx + 2,
1
y ꢂ , ꢂz + 12], which is only slightly longer than the sum of the
2
˚
An et al., 2008; Ma et al., 2009; Guo et al., 2010; He et al., 2010).
In addition to ꢀ–ꢀ interactions, the zigzag chains in (I) are
also interconnected via hydrogen bonding, yielding a three-
dimensional metal–organic framework (Fig. 3). The hydrogen-
bonding geometry is listed in Table 2. Three of the four
hydrogen bonds are between the H2O molecule and O atoms
from different carboxylate groups, while the fourth is between
amine atom H5 from dipya and uncoordinated atom O3 from
the monodentate C18/O3/O4 group (Table 2). Atom O3 acts
as a double hydrogen-bond acceptor from the already
mentioned atom H5 and from atom H11 of the uncoordinated
water molecule. The remaining H atom (H12) of the water
molecule very likely participates in two hydrogen bonds, and
therefore this bond can be described as bifurcated. The Dꢀ ꢀ ꢀA
distance for O5—H12ꢀ ꢀ ꢀO1iii is longer but the angle is
acceptable, which is not the case for O5—H12ꢀ ꢀ ꢀO4iii, where
the distance is suitable but a much smaller angle [127 (3)ꢁ] is
found (distances and symmetry codes are in Table 2).
Since the initial positions of the H atoms were not found in
ÁF maps but were generated using a combined geometric and
force-field approach (Nardelli, 1999), they can not be
considered as very reliable. For a better insight into the
strength of the hydrogen bonding in (I), thermogravimetric
and differential scanning calorimetric (TG and DSC) analyses
were performed. It was found that the TG and DSC curves of
(I) are practically identical to the recently published curves of
the corresponding polycrystalline complex (Rogan et al.,
2011), so only dehydration will be discussed here. The dehy-
dration is a single-step process and the mass loss of 4.5%
between 396 and 450 K is attributed to the loss of the solvent
H2O molecule (calculated 4.3%). The endothermic peak in the
DSC curve relating to the dehydration process gives a molar
enthalpy of 50.4 kJ molꢂ1 which, together with the high final
dehydration temperature, indicates strong hydrogen bonding.
A similar value of the dehydration molar enthalpy was
recently found for an MnII complex {[Mn(C5O5)(bipy)-
van der Waals radii (2.92 A; Bondi, 1964), should also be
mentioned. Since the O2—Cu1—O3i angle is 160.56 (5)ꢁ, the
Cu1 environment could also be described as an extremely
deformed very elongated octahedron.
As usual, dipya is a chelating ligand in (I), while the ipht
anions act as bridging tridentate ligands with monodentate
(C18/O3/O4) and chelating (C11/O1/O2) carboxylate groups,
forming one-dimensional zigzag chains running along the b
axis (Fig. 2). The distance between two Cu1 atoms bridged by
˚
the ipht anion is 11.7216 (5) A, while the shortest interchain
˚
Cu1ꢀ ꢀ ꢀCu1 distance is 7.9931 (4) A. Very similar zigzag chains
are found in [Zn(ipht)(1-methylimidazole)2]n (Zhao, 2008a),
[Co(ipht)(1-ethylimidazole)2]n (Zhao, 2008b), [Cu(tbipht)-
(bipy)]n (bipy is 2,20-bipyridine and tbipht is 5-tert-butyliso-
phthalate; Li & Huang, 2008) and {[Mn(ipht)(bipy)(H2O)2]ꢀ-
H2O}n (Ma, Hu et al., 2010). In (I), the ipht aromatic ring and
the entire dipya ligand are nearly perpendicular to each other
[dihedral angle = 82.20 (6)ꢁ]. Considering the bridging role of
the ipht anion, the value of this angle is probably the main
reason for the existence of the zigzag chains.
All the dipya ligands in (I) are oriented approximately
parallel to the (102) plane (Fig. 3). This enables stacking of the
chains by face-to-face ꢀ–ꢀ interactions between neighbouring
dipya ligands. Although in mixed metal–organic complexes
(Rogan et al., 2006) the dihedral angle between the two
pyridine rings of dipya can reach 29ꢁ, in (I) this angle is very
small [7.68 (7)ꢁ] and both pyridine rings are involved in ꢀ–ꢀ
interactions. The shortest distances between C atoms of
v
˚
neighbouring dipya ligands are 3.307 (4) A for C5ꢀ ꢀ ꢀC5 and
v
1
2
˚
3.303 (4) A for C6ꢀ ꢀ ꢀC6 [symmetry code: (v) ꢂx, y, ꢂ z],
with corresponding Cgꢀ ꢀ ꢀCgv separations between aromatic
˚
rings of 3.502 (7) and 3.678 (7) A, respectively; these values
confirm strong face-to-face ꢀ–ꢀ interactions (Janiak, 2000). In
this way, hydrophilic and hydrophobic layers parallel to the bc
plane are formed. With a few exceptions, e.g. where ꢀ–ꢀ
interactions with centroid–centroid distances of around 3.2
ꢃ
Acta Cryst. (2011). C67, m230–m233
Rogan et al.
[Cu(C8H4O4)(C10H9N3)]ꢀH2O m231

metal-organic compounds
Table 1
Selected bond lengths (A).
(H2O)]ꢀH2O}n (Chen et al., 2010), where the solvent H2O
˚
molecule participates in two hydrogen bonds but with signif-
˚
icantly shorter Dꢀ ꢀ ꢀA distances (2.88–2.98 A). At the same
Cu1—O4i
Cu1—O1
Cu1—N2
1.9250 (15)
1.9356 (15)
1.9650 (17)
Cu1—N1
Cu1—O2
Cu1—O3i
1.9806 (18)
2.546 (2)
3.0229 (18)
time, a detailed analysis of analogous terephthalate complexes
(Rogan & Poleti, 2004) showed that the mean energy of a
hydrogen bond should be about 16 kJ molꢂ1 or slightly higher.
Therefore, the hydrogen bonds in (I) are stronger than
expected and it is evident that all three hydrogen bonds in
which the solvent H2O molecule participates really exist.
Metal–organic polymers where ipht is coordinated as a
bridging tridentate ligand with monodentate and chelate
carboxylate groups are quite rare among the numerous ipht
complexes. To the best of our knowledge, in total four such
transition metal complexes have been described so far (Li &
Wei, 2007; Cui et al., 2009; Su et al., 2009; Al-Hashemi et al.,
2010), but two of them (Su et al., 2009; Al-Hashemi et al., 2010)
contain two chemically different ipht anions, i.e. one anion is
not a bridging tridentate ligand. In addition, five complexes
are known containing derivatives of ipht coordinating in the
same mode to CuII (Guo et al., 2010) or CoII (Du et al., 2009;
Zeng et al., 2009) as the central atoms. The predominant
coordination number of the transition metal atoms in these
complexes is 6.
1
1
1
2
Symmetry code: (i) ꢂx þ ; y ꢂ ; ꢂz þ .
2
2
Table 2
Hydrogen-bond geometry (A, ).
ꢁ
˚
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
O5—H11ꢀ ꢀ ꢀO3i
O5—H12ꢀ ꢀ ꢀO1ii
O5—H12ꢀ ꢀ ꢀO4iii
N3—H5ꢀ ꢀ ꢀO3iv
0.84 (3)
0.85 (2)
0.85 (2)
0.86
2.21 (3)
2.51 (3)
2.53 (4)
1.95
3.017 (4)
3.346 (3)
3.117 (4)
2.813 (3)
159 (2)
167 (3)
127 (3)
178
1
2
1
2
1
2
1
2
1
2
Symmetry codes: (i) ꢂx þ ; y ꢂ ; ꢂz þ ; (ii) ꢂx þ ; ꢂy þ ; ꢂz þ 1; (iii) x; ꢂy þ 1,
1
2
1
2
1
2
z þ ; (iv) x ꢂ ; y ꢂ ; z.
Crystal data
3
˚
[Cu(C8H4O4)(C10H9N3)]ꢀH2O
V = 3394.1 (3) A
Z = 8
Mo Kꢂ radiation
ꢃ = 1.32 mmꢂ1
T = 295 K
Mr = 416.87
Monoclinic, C2=c
a = 23.2351 (11) A
˚
The similarities in geometry between (I) and comparable
metal–organic polymers are related to the dihedral angle
between the plane of the benzene ring of the polycarboxylate
ligand and the chelate or monodentate carboxylate group, as
well as that between the planes of the chelate and mono-
dentate carboxylate group. With one exception (Table 3),
these angles do not exceed 25ꢁ. Accordingly, a general char-
acteristic of (I) and related complexes containing ipht or its
derivatives is that these kinds of ligands do not deviate very
much from planarity. It seems that higher dihedral angles in
several complexes (Table 3) are associated with the bulkiness
of the second ligand (Al-Hashemi et al., 2010), the bulkiness of
the substituent on the ipht ligand (Du et al., 2009) or the
overall bulkiness of the complex unit (Guo et al., 2010). The
same coordination mode for polycarboxylate ligands is
presumably the main explanation for the minor deviations
between the stated dihedral angles.
˚
b = 11.7216 (4) A
˚
c = 13.7825 (7) A
0.29 ꢄ 0.16 ꢄ 0.10 mm
ꢁ = 115.285 (6)ꢁ
Data collection
Oxford Gemini-S diffractometer
Absorption correction: multi-scan
(CrysAlis PRO; Oxford
Diffraction, 2009)
Tmin = 0.700, Tmax = 0.879
8071 measured reflections
3214 independent reflections
2473 reflections with I > 2ꢄ(I)
Rint = 0.021
Refinement
R[F2 > 2ꢄ(F2)] = 0.030
wR(F2) = 0.076
S = 0.96
3214 reflections
250 parameters
2 restraints
H atoms treated by a mixture of
independent and constrained
refinement
ꢂ3
˚
Áꢅmax = 0.45 e A
Áꢅmin = ꢂ0.34 e A
ꢂ3
˚
C-bound H atoms and amine atom H5 of the dipya ligand were
˚
positioned geometrically and refined as riding, with C—H = 0.93 A
˚
and N—H = 0.86 A, and with Uiso(H) = 1.2Ueq(C,N). The initial
Experimental
Single crystals of (I) were obtained by a modification of the slow-
diffusion method. A mixture containing Cu(NO3)2ꢀ3H2O (60 mg,
0.25 mmol), di-2-pyridylamine (43 mg, 0.25 mmol) and H2ipht
(42 mg, 0.25 mmol) was dissolved in dimethyl sulfoxide (12 ml). The
mixture was stirred for 10 min and then transferred to a small test
tube. A dilute solution of Na2ipht in H2O (0.05 M) was then layered
on top carefully and very slowly in order to minimize mixing of the
solutions. The first prismatic green crystals of (I) appeared within
24 h, but single crystals of a suitable size for analysis were filtered off
after about 10 d. The complex is stable in air and insoluble in all
common solvents. The thermal properties of (I) were examined from
room temperature up to 973 K on an SDT Q600 TGA/DSC instru-
ment (TA Instruments). The heating rate was 20 K minꢂ1 using less
than 10 mg sample mass. The furnace atmosphere consisted of dry
positions of water atoms H11 and H12 were calculated using the
program HYDROGEN (Nardelli, 1999) and then refined with O—H
˚
restrained to 0.85 (1) A and with Uiso(H) = 1.5Ueq(O5).
Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell
refinement: CrysAlis PRO; data reduction: CrysAlis PRO;
program(s) used to solve structure: SIR97 (Altomare et al., 1999);
program(s) used to refine structure: SHELXL97 (Sheldrick, 2008);
molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and
Mercury (Macrae et al., 2008); software used to prepare material for
publication: publCIF (Westrip, 2010) and PARST (Nardelli, 1995).
This work was supported financially by the Ministry for
Education and Science of the Republic of Serbia (grant No.
45007).
nitrogen at a flow rate of 100 cm3 minꢂ1
.
ꢃ
m232 Rogan et al. [Cu(C8H4O4)(C10H9N3)]ꢀH2O
Acta Cryst. (2011). C67, m230–m233

metal-organic compounds
Table 3
Selected dihedral angles (ꢁ) for (I) and some related compounds.
3-bpo is 2,5-bis(3-pyridyl)-1,3,4-oxadiazole, mipht is 5-methylisophthalate, moipht is 5-methoxyisophthalate, 5-NH2-ipht is 5-aminoisophthalate, phen is 1,10-
phenanthroline, tbipht is 5-tert-butylisophthalate, dm4bt is 2,20-dimethyl-4,40-bithiazole and tib is 1,3,5-triimidazol-1-ylbenzene.
Compound
Benzene ring–chelate
COOꢂ group
Benzene ring–monodentate
COOꢂ group
Chelate–monodentate
COOꢂ group
(I)
9.37
6.43
0.81
7.23
7.98
9.10
18.89
12.88
4.75
6.07
12.64
7.80
17.92
12.24
3.15
9.34
13.65
8.61
25.15
20.12
11.50
21.64
23.69
9.04
a
{[Cu(ipht)(C6H9N3)(H2O)]ꢀC6H9N3}n
b
[Ni(ipht)(2,40-bipyridine)2(H2O)]n
c
{[Cu(mipht)(3-bpo)(H2O)]ꢀ0.5H2O}n
c
{[Cu(moipht)(3-bpo)(H2O)]ꢀ0.5H2O}n
d
{[Co(5-NH2-ipht)(4,40-bipyridine)0.5(H2O)]ꢀ2H2O}n
e
{[Co(tbipht)(H2O)(phen)]ꢀH2O}n
2.79
[{Cu(ipht)(dm4bt)(H2O)}4ꢀ2H2O]f
23.45
5.51
6.38
g
{[Zn2(ipht)2(H2O)(tib)]ꢀ2H2O}n
e
[Co4(tbipht)4(2,20-bipyridine)4(H2O)4]n
26.16
32.48
References: (a) Li & Wei (2007); (b) Cui et al. (2009); (c) Guo et al. (2010); (d) Zeng et al. (2009); (e) Du et al. (2009); (f) Al-Hashemi et al. (2010); (g) Su et al. (2009).
Liu, D., Li, H. X., Liu, L. L., Wang, H. M., Li, N. Y., Ren, Z. G. & Lang, J. P.
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