Synthetic Metals 159 (2009) 45–51

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Synthetic Metals
journal homepage: www.elsevier.com/locate/synmet

Synthesis and structure of charge transfer salts of tetrathiafulvalene (TTF) and

tetramethyl-TTF with 2,4,7-trinitro and 2,4,5,7-tetranitro-9-fluorenone
Eric W. Reinheimer a , J.R. Galán-Mascarós b,∗ , Kim R. Dunbar a,∗
a
Department of Chemistry, Texas A&M University, College Station, TX 77842-3012, USA
b
Instituto de Ciencia Molecular, Universidad de Valencia, Polígono de la Coma, s/n, 46980 Paterna, Spain

a r t i c l e i n f o a b s t r a c t

Article history: Charge transfer salts of tetrathiafulvalene (TTF) and tetramethyltetrathiafulvalene (TMTTF) with the
Received 23 June 2008 organic acceptors 2,4,7-trinitro-9-fluorenone and 2,4,5,7-tetranitro-9-fluorenone have been prepared
Received in revised form 22 July 2008 and characterized. The compounds (TTF)[TENF] (1), (TTF)3 [TRNF]2 (2) and (TMTTF)[TRNF] (3) contain
Accepted 22 July 2008
mixed stacks of alternating TTF and nitrofluorenone units. Surprisingly, the degree of charge transfer that
Available online 1 October 2008
occurs in these salts is not controlled solely by the redox potentials of the building blocks, but apparently
also by the most effective intermolecular interactions in the solid, as determined from the crystal struc-
Keywords:
tures obtained. These three compounds exhibit poor electron delocalization and therefore they behave as
Charge transfer salts
Tetrathiafulvalene (TTF)
diamagnetic insulators.
Tetramethyltetrathiafulvalene (TMTTF) Published by Elsevier B.V.

1. Introduction containing species. Fluorenone derivatives have recently been

Charge transfer salts and radical salts containing oxidized
species of tetrathiafulvalene (TTF) and its derivatives represent
the most numerous and important family of molecular conduc-
tors, with many examples of molecular metals and superconductors
having been reported in recent years [1]. Most of the success-
ful examples derive from the radical salt approach, in which
the overall cationic charge of the oxidized TTFs is counter bal-
anced by inorganic anions [2], “innocent” or “electroactive”,
which represents a successful approach towards multifunc-
tional conductors [3]. In the case of charge transfer salts, a
purely organic approach is possible. The most studied example
is that of the 1:1 organic complex TTF-TCNQ (TCNQ = 7,7,8,8-
tetracyanoquinodimethane) [4]. In this material, there is partial
charge transfer between the donor and acceptor in the solid
state, wherein the different molecules stack as segregated cationic
and anionic chains of TTF and TCNQ, respectively. This material
represents the paradigm for preparing a pure organic conduc-
tor.
In the same vein, other organic acceptors have been sys-
tematically investigated [5–7], but few detailed studies have
been reported, especially for organic acceptors other than nitrile-
∗ Corresponding authors. Tel.: +1 979 845 5235; fax: +1 979 845 7177.
E-mail addresses: jose.r.galan@uv.es (J.R. Galán-Mascarós),
dunbar@mail.chem.tamu.edu (K.R. Dunbar).
explored as potential organic acceptors in the formation of charge
transfer complexes. The interest in this area has been heightened
by a few examples such as the combination of cyano-derivatives
with BEDO-TTF (BEDO-TTF = bis(ethylenedioxy)tetrathiafulvalene)
to yield organic metals [8]. Also, nitro-containing derivatives have
been combined with trimeric clusters of Au(I) to yield interesting
spectroscopic properties [9]. Nitro carboxylated derivatives of flu-
orene, which are chemically similar to the nitrofluorenone family
of acceptors, have also been combined with TTF and their result-
ing level of charge transfer was probed using infrared and Raman
spectroscopies [10].
In order to explore and understand the possible role of flu-
orenone derivatives in the preparation of charge transfer salts
we have systematically prepared and crystallized the TTF and
tetramethyltetrathiafulvalene (TMTTF) salts of 2,4,7-trinitro-9-
fluorenone, and 2,4,5,7-trinitro-9-fluorenone. It should be noted
that the (TTF)[2,7-dinitro-9-flourenone] charge transfer com-
plex was first reported in 1989 and later discussed in 1993,
and reported to be an insulator [11,12]. This can be under-
stood by the fact that there is a large difference between
their redox potentials, E1/2 (TTF) = +0.23 V and E1/2 (2,7-dinitro-9-
fluorenone) = −0.68), which is expected to lead to a very small
effective charge transfer, with both molecules remaining essen-
tially neutral. By increasing the number of nitro groups one
can enhance the electron accepting properties of the fluorenone
derivatives, for example E1/2 (2,4,7-trinitro-9-fluorenone) = −0.42 V
(1) and E1/2 (2,4,5,7-tetranitro-9-fluorenone) = +0.14 V (2), which

0379-6779/$ – see front matter. Published by Elsevier B.V.

doi:10.1016/j.synthmet.2008.07.017
46 E.W. Reinheimer et al. / Synthetic Metals 159 (2009) 45–51

Table 1 Table 3
X-ray crystallographic data for compounds 1–3 Bond distances for 2 in Å

Compound S(1)–C(1) 1.743(3) C(1)–C(2) 1.326(4)

S(1)–C(3) 1.756(3) C(3)–C(3) 1.362(5)
1: (TTF)[TENF] 2: (TTF)3 [TRNF]2 3: (TMTTF)[TRNF]
S(2)–C(2) 1.742(3) C(4)–C(5) 1.327(4)
Formula C19 H8 N4 O9 S4 C44 H22 N6 O14 S12 C23 H17 N3 O7 S4 S(2)–C(3) 1.749(3) C(6)–C(6) 1.344(6)
Formula weight 564.57 1243.52 575.64 S(3)–C(4) 1.741(3) C(7)–C(8) 1.324(4)
Space group P-1 P-1 P-1 S(3)–C(6) 1.766(3) C(9)–C(9) 1.335(6)
a (Å) 7.300(2) 10.607(2) 7.490(2) S(4)–C(5) 1.737(3) C(10)–C(11) 1.375(4)
b (Å) 11.040(2) 10.742(2) 10.030(2) S(4)–C(6) 1.764(3) C(10)–C(22) 1.379(4)
c (Å) 13.690(3) 10.931(2) 16.294(3) S(5)–C(8) 1.741(3) C(11)–C(12) 1.378(4)
˛ (◦ ) 92.20(3) 89.45(3) 97.46(3) S(5)–C(9) 1.772(3) C(12)–C(13) 1.481(4)
ˇ (◦ ) 91.80(3) 83.16(3) 91.85(3) S(6)–C(7) 1.744(3) C(12)–C(20) 1.508(4)
 (◦ ) 97.00(3) 75.31(3) 99.20(3) S(6)–C(9) 1.759(3) C(13)–C(14) 1.483(4)
V (Å3 ) 1093.55 1195.95 1196.35 N(1)–O(1) 1.227(3) C(14)–C(15) 1.409(4)
Z 2 1 2 N(1)–O(2) 1.224(3) C(14)–C(19) 1.412(4)
 (mm−1 ) 0.498 0.619 0.450 N(1)–C(10) 1.469(4) C(15)–C(16) 1.377(4)
Reflns. collected 2910 3424 3389 N(2)–O(5) 1.230(3) C(16)–C(17) 1.383(4)
Reflns. I > 2 2060 2933 1711 N(2)–O(6) 1.223(3) C(17)–C(18) 1.383(4)
R1a 0.0419 0.0362 0.0912 N(2)–C(16) 1.474(4) C(18)–C(19) 1.387(4)
wR2 0.1341b 0.1153c 0.2445d N(3)–O(3) 1.230(3) C(19)–C(20) 1.508(4)
  N(3)–O(4) 1.210(3) C(20)–C(21) 1.400(4)
a
R1 = [ |Fo | − |Fc |]/ |Fo |. N(3)–C(21) 1.473(3) C(21)–C(22) 1.387(4)
 2
 2
1/2 2
O(7)–C(13) 1.216(3)
b
wR2 = [w(Fo2 − Fc2 ) ]/ [w(Fo2 ) ] , w = 1/[ 2 (Fo2 ) + (0.0596P) ],

where P = [Fo2 + 2Fc2 )]/3.

 2
 2
1/2 2 uct formed between TMTTF and 2,4,7-trinitro-9-fluorenone (3) was
c
wR2 = [w(Fo2 − Fc2 ) ]/ [w(Fo2 ) ] , w = 1/[ 2 (Fo2 ) + (0.0432P) +
carried out in a similar manner as described for adducts 1 and 2,
0.5533P], where P = [Fo2 + 2Fc2 )]/3.
the only modification being the use of dichloromethane instead of
  1/2
d
wR2 = [w(Fo2 − Fc2 ) ]/
2 2
[w(Fo2 ) ]
2
, w = 1/[ 2 (Fo2 ) + (0.1313P) ], where acetonitrile to dissolve the TMTTF. Upon mixing the nitrofluorenone
and TMTTF, no spontaneous color change occurred. Over the period
P = [Fo2 + 2Fc2 )]/3.
of one hour, however, air-stable, X-ray quality black needles formed
that were separated from the mother liquor by filtration.
should have an effect on the packing and electronic properties of
their respective charge transfer salts [13]. 2.2. Structural characterization

2. Experimental In order to probe the solid-state structures of the adducts, a black

2.1. Synthesis
The adducts 1 and 2 were formed by combining concentrated
acetonitrile solutions of TTF with a slight excess of the nitrofluo-
renone derivatives in warm acetonitrile. Upon addition of the pale
yellow nitrofluorenone solution to the intense yellow solutions of
TTF, a spontaneous color change to a slight green color ensues. Upon
slow evaporation in air, air-stable, X-ray quality black needles of 1
and black blocks of 2 formed over the period of one night and one
week for the compounds, respectively. The synthesis of the prod-
needle of dimensions 0.28 mm × 0.16 mm × 0.10 mm for complex 1
and a black block of dimensions 0.40 mm × 0.17 mm × 0.05 mm for
complex 2 were secured to a crystallographic loop using silicon
oil and transferred to a SMART 1000 CCD diffractometer. A black
needle of dimensions 0.39 mm × 0.08 mm × 0.02 mm for complex 3
was transferred in the same manner to a SMART APEX diffractome-
ter. All data collections were conducted at 110 ± 2 K with graphite
monochromated Mo-K␣ (␣ = 0.71073 Å) radiation.
The data were corrected for Lorentz and polarization effects.
The Siemens SAINT software package was used to integrate
the frames, and the data were corrected for absorption using

Table 2 Table 4
Bond distances for 1 in Å Bond distances for 3 in Å

S(1)–C(1) 1.771(4) O(9)–C(17) 1.225(4) S(1)–C(6) 1.756(8) C(3)–C(4) 1.492(11)

S(1)–C(3) 1.763(4) C(1)–C(2) 1.350(5) S(1)–C(7) 1.776(7) C(5)–C(6) 1.334(11)
S(2)–C(2) 1.753(4) C(3)–C(4) 1.374(5) S(2)–C(6) 1.781(8) C(7)–C(8) 1.327(12)
S(2)–C(3) 1.793(4) C(5)–C(6) 1.340(6) S(2)–C(8) 1.749(9) C(7)–C(9) 1.509(11)
S(3)–C(4) 1.784(4) C(7)–C(8) 1.388(6) S(3)–C(2) 1.752(8) C(8)–C(10) 1.510(11)
S(3)–C(5) 1.748(4) C(7)–C(19) 1.400(6) S(3)–C(5) 1.775(8) C(11)–C(12) 1.393(12)
S(4)–C(4) 1.763(4) C(8)–C(9) 1.406(5) S(4)–C(3) 1.769(8) C(11)–C(23) 1.370(11)
S(4)–C(6) 1.756(4) C(9)–C(10) 1.415(5) S(4)–C(5) 1.735(8) C(12)–C(13) 1.381(11)
N(1)–O(1) 1.229(5) C(10)–C(11) 1.516(5) N(1)–O(1) 1.229(9) C(13)–C(14) 1.480(12)
N(1)–O(2) 1.246(5) C(10)–C(18) 1.424(5) N(1)–O(2) 1.210(9) C(13)–C(21) 1.394(11)
N(1)–C(7) 1.501(5) C(11)–C(12) 1.411(5) N(1)–C(11) 1.482(11) C(14)–C(15) 1.494(10)
N(2)–O(3) 1.247(4) C(11)–C(16) 1.421(5) N(2)–O(5) 1.219(9) C(15)–C(16) 1.363(12)
N(2)–O(4) 1.244(4) C(12)–C(13) 1.400(5) N(2)–O(6) 1.237(9) C(15)–C(20) 1.412(11)
N(2)–C(9) 1.486(5) C(13)–C(14) 1.397(5) N(2)–C(17) 1.461(10) C(16)–C(17) 1.397(11)
N(3)–O(5) 1.248(4) C(14)–C(15) 1.385(5) N(3)–O(3) 1.221(9) C(17)–C(18) 1.375(11)
N(3)–O(6) 1.236(4) C(15)–C(16) 1.406(5) N(3)–O(4) 1.220(9) C(18)–C(19) 1.362(11)
N(3)–C(12) 1.485(5) C(16)–C(17) 1.499(5) N(3)–C(22) 1.476(10) C(19)–C(20) 1.397(11)
N(4)–O(7) 1.243(4) C(17)–C(18) 1.511(5) O(7)–C(14) 1.224(9) C(20)–C(21) 1.511(11)
N(4)–O(8) 1.239(4) C(18)–C(19) 1.395(5) C(1)–C(2) 1.508(10) C(21)–C(22) 1.393(11)
N(4)–C(14) 1.497(5) C(2)–C(3) 1.340(12) C(22)–C(23) 1.377(11)
 E.W. Reinheimer et al. / Synthetic Metals 159 (2009) 45–51 47

Fig. 1. X-ray structure of (TTF)[TENF] (1).

Fig. 2. X-ray structure of (TTF)3 [TRNF]2 (2).

the SADABS program [14]. The structures were solved by direct

methods by the use of the SHELXS-97 program [15], in the Bruker
SHELXTL v5.1 interface [16], in the XSEED software package [17].
The SHELXL-97 program [18], was employed to refine all non-
hydrogen atoms with anisotropic thermal parameters by full matrix
least squares calculations on F2 . Hydrogen atoms were inserted at
calculated positions and constrained with isotropic thermal param-

Fig. 4. Projection of the crystal structure of 1 in the bc plane, and representation of

the alternating chains that run along the a axis.

eters. Crystallographic information is shown in Table 1, while bond

Fig. 3. X-ray structure of (TMTTF)[TENF] (3).
distances for 1–3 are presented in Tables 2–4. X-ray crystallo-
graphic structures and packing diagrams for 1–3 are shown in
Figs. 1–6. CCDC 612659–612661 contain the supplementary crys-
tallographic data for this paper. These data can be obtained free
of charge from the Cambridge Crystallographic Data Center via
www.ccdc.cam.ac.uk/data request/cif.
48 E.W. Reinheimer et al. / Synthetic Metals 159 (2009) 45–51

Fig. 5. Projection of the crystal structure of 2 in the bc plane, and representation of the alternating chains that run parallel to this plane.
 E.W. Reinheimer et al. / Synthetic Metals 159 (2009) 45–51 49

Fig. 6. Projection of the crystal structure of 3 in the bc plane, and representation of the alternating chains that run parallel to this plane.

2.3. Magnetic characterization
Bulk magnetization measurements were carried out on poly-
crystalline samples with a Quantum Design MPMS7 magnetometer.
The thermal dependence of the magnetic susceptibility was stud-
ied in an applied field of 1000 G in the temperature range 2–300 K.
Susceptibility measurements revealed that all three compounds are
essentially diamagnetic, as expected, with no temperature inde-
pendent paramagnetic (TIP) contribution.
intermolecular donor–acceptor interactions also dictate the pack-
ing in the solid state, wherein, rather than segregated stacks,
one observes an alternating integrated stacking of the molecular
species. The strength of these and other intermolecular interac-
tions determine the crystal structure of these materials. The organic
molecules appear with non-integer charge, due to the presence of
partial charge transfer, as estimated from the TTF bonding distances
which are very sensitive to its oxidation level, whereas the nitroflu-
orenone molecules did not reveal any obvious structural alterations.

3. Results and discussion 3.1. (TTF)[TENF] (1)

In all cases, the interaction between donor and acceptor favors The solid state structure of 1 contains 1:1 mixed, alternating
the formation of mixed solids with strong intermolecular inter- stacks of donor and acceptor molecules along the a axis forming
actions between the TTF and nitrofluorenone units. These strong 1D chains (Fig. 4) in a pseudo-tetragonal packing arrangement.
50 E.W. Reinheimer et al. / Synthetic Metals 159 (2009) 45–51
The TTF molecule is not planar, and displays a slight distor-
tion from planarity by an angle of 7◦ between the planes of
the dithiole rings. From the C–C and C–S bonding distances, a
charge of +0.18 per TTF molecule can be estimated according to
Coppens method [19]. The nitrofluorenone molecule displays a
torsion angle collinear with the C2 axis that bisects the central
five-membered ring resulting in a twisted conformation for the
central fluorenone moiety. In most cases, the fluorenone moiety
of the nitrofluorenone molecules remain planar, while their con-
stituent nitro groups deviate from planarity. A single nitro group
is coplanar with each half of the molecule (torsion angles below
3◦ ), while the second nitro group in each half, in the 4- and
5-positions, differs from planarity by torsion angles of 25◦ and
30◦ . This conformation involves weak intermolecular interactions
between these two nitro groups, with N· · ·O distances as short
as 2.694(5) Å. Another interesting feature of the tetranitrofluo-
renone molecule is the bond length of the carbonyl group defined
by C(12) and O(3) is 1.226(4) Å, whereas the neutral molecule
shows a carbonyl bond distance of 1.205(3) Å. This increase in
carbonyl bond distance is indicative of electron donation from
TTF to the carbonyl group of tetranitrofluorenone. There are no
close interactions between chains, with all contacts being essen-
tially the sum of van der Waals radii. There is a weak interaction
between adjacent chains between a nitro group and a sulfur atom
(O3· · ·S1 = 2.981(4) Å).
3.2. (TTF)3 [TRNF]2 (2)
In this case, the stoichiometry is 3:2 instead of 1:1, as in the
other compounds, and is composed of mixed stacks of alternat-
ing donor and acceptor units as well as isolated TTF molecules
(Fig. 5). The asymmetric unit contains a single trinitrofluorenone
molecule and three half-molecules of TTF (A–C). Two of the
three crystallographically independent TTF molecules (A and B)
form alternating stacks with the trinitrofluorenone acceptor par-
allel to the [0 1 −1] direction on the bc plane, with a sequence
· · ·A· · ·TRNF· · ·B· · ·TRNF· · · [9]. Molecule C appears in the inter-
chain separation with the plane perpendicular to the chains. From
the intramolecular bonding distance, there are two TTF molecules
that appear neutral (B and C) while molecule A has an estimated
charge of +0.3. This was expected for molecule C because it is
completely isolated which usually leads to neutral TTF. The dif-
ference charges observed for the TTFs in the chains are in good
agreement with the intermolecular distances. Indeed, the chains
do not show a regular stack, with very close contacts between
molecule A and the TRNF molecules (3.01(5) Å between S1 and
the mean plane of the two adjacent TRNF molecules), and much
longer for molecule B (3.35(5) and 3.43 Å between S3 and the
mean plane of the two adjacent TRNF molecule). Thus the struc-
ture can be considered as being composed of sandwiched trimers
TRNF· · ·TTF(A)· · ·TRNF with effective charge transfer, separated by
neutral TTF molecules.
Along the chain, the molecules are related by a center of
symmetry, and thus consecutive TRNF molecules show opposite
orientation, regarding the C O group and appear with completely
planar conformation including the nitro groups, which exhibit
a maximum deviation of 7◦ from planarity. In the case of the
4-nitro group, this coplanarity is the result of weak intramolec-
ular H-bonding interactions, as short as O3· · ·C22 = 2.633(5) and
O4· · ·C18 = 2.832(6) Å. There are no close contacts between stacks
or with the neutral and isolated TTF molecule. The most relevant
intermolecular interactions come between the C O group with sul-
fur atoms from TTF A molecules, the ones with highest positive
charge (S1· · ·O7 = 2.904(8) Å).
3.3. (TMTTF)[TRNF] (3)
This compound also exhibits mixed 1:1 stacks of alternating
TMTTF and nitrofluorenone units (Fig. 6) which form along the a
axis in a pseudo-hexagonal packing motif. There is only one crys-
tallographically independent neutral TTF molecule, as estimated
from the intermolecular bonding distances [19]. The interplanar
distance is 3.288 Å. The trinitrofluorenone molecule also shows a
planar configuration, with torsion angles up to 27◦ for the cen-
tral 4-nitro group. The loss of coplanarity of this group with
respect to compound 2 is the result of stronger intermolecular
interactions. In this case in addition to weak intramolecular H-
bonding (O3· · ·C22 = 2.633(7) Å) there are also O· · ·N intermolecular
interactions as short as O4· · ·C18 = 2.832(6) Å. Interchain interac-
tions are much weaker, and no significant H-bonding is observed,
with the shortest contact appearing between a nitro group and
aromatic carbons from fluorenone molecules in adjacent chains
(O4· · ·C19 = 2.844(6) Å). It is obvious that the packing arrangement
is dominated by ␲–␲ interactions.
4. Conclusion
We have analyzed the crystal structures of products formed by
the direct reaction of TTF and TMTTF with tri- and tetranitrofluo-
renone. We have found that there is partial charge transfer in the
salts containing TTF, while none occurs in the TMTTF. The crys-
tal packing in all cases consists of mixed donor–acceptor stacks.
The absence of segregated stacks of donors and acceptors must be
related to the low ionicity of the TTF molecules, that as almost
neutral entities do not show such strong S· · ·S interactions. Our
results indicate that the degree of charge transfer in these com-
pounds depends on the solid state structure, controlled mostly by
␲–␲ and other very weak intermolecular interactions. It is surpris-
ing to observe that in the TTF case, the stronger electron donor,
tetranitrofluorenone, did not yield a product with the most effi-
cient charge transfer, such as was found for trinitrofluorenone with
an estimated +0.3 charge for TTF. The reason for this is obviously
structural since, in the trinitrofluorenone derivative, two fluo-
renone molecules are accepting electron density from only one TTF
molecule, thereby forming trimers with close interactions, while in
the tetranitrofluorenone there is a regular stack in the chain. Apart
from the interesting structural features controlling the degree of
charge transfer from the TTF molecules, the weak charge transfer
found in all cases renders these compounds diamagnetic insulators.
Stronger electron acceptors could be used with similar geometries
to obtain increased electrical conductivity for these types of mate-
rials.
Acknowledgements
The authors would like to thank the National Science Foundation
and the Robert A. Welch Foundation for financial support as well
as for the grants used to purchase the X-ray diffractometer (NSF
9807975) and SQUID magnetometer (NSF 9974899). JRGM thanks
the Generalitat Valenciana for a travel grant.
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