X-ray analysis at 150 K, synthesis and theoretical calculations of 1-naphthaleneacrylic acid

Article abstract of DOI:10.1007/s11224-011-9873-1

The X-ray structure, synthesis, theoretical calculation and IR spectra of 1-naphthaleneacrylic acid are reported. The titled compound crystallizes in the monoclinic C 2/c space group with unit cell parameters: a = 14.556(3), b = 5.1332(10), c = 26.832(5) A , β = 97.02(3), V = 1989.8(7) A³, Z = 8 and form typical centrosymmetric hydrogen-bonded dimers. Theoretical calculations of 1-naphthylacrylic acid isolated molecule and hydrogen-bonded dimer have been carried out using density functional theory at the B3LYP level. For optimized structures the vibrational spectra have been then calculated and compared with experimental IR spectrum. The assignment and characterization of theoretical vibrational spectra were based on the potential energy distribution analysis. This comparison has shown that the theoretical spectrum for the dimer structure is in good agreement with the experimental one. Structural comparisons with naphthalene, and with some substituted 2-propenoic acids have shown influence of the substituent on conformation of the naphthalene ring or 2-propenoic moiety. Springer Science+Business Media, LLC 2012.

Full text of DOI:10.1007/s11224-011-9873-1

Struct Chem (2012) 23:325–332
DOI 10.1007/s11224-011-9873-1
ORIGINAL RESEARCH
X-ray analysis at 150 K, synthesis and theoretical calculations
of 1-naphthaleneacrylic acid
•
Aleksandra Tyl Elzbieta Chełmecka
•
_
Magdalena Jabłonska Maria Nowak
•
•
´
Joachim Kusz Karol Pasterny Roman Wrzalik
•
•
Received: 18 February 2011 / Accepted: 26 August 2011 / Published online: 14 September 2011
Ó Springer Science+Business Media, LLC 2011
Abstract The X-ray structure, synthesis, theoretical cal-
culation and IR spectra of 1-naphthaleneacrylic acid are
reported. The titled compound crystallizes in the mono-
clinic C 2/c space group with unit cell parameters:
agreement with the experimental one. Structural com-
parisons with naphthalene, and with some substituted
2-propenoic acids have shown influence of the substituent
on conformation of the naphthalene ring or 2-propenoic
moiety.
˚
a = 14.556(3), b = 5.1332(10), c = 26.832(5) A, b =
3
˚
97.02(3)°, V = 1989.8(7) A , Z = 8 and form typical
centrosymmetric hydrogen-bonded dimers. Theoretical
calculations of 1-naphthylacrylic acid isolated molecule
and hydrogen-bonded dimer have been carried out using
density functional theory at the B3LYP level. For opti-
mized structures the vibrational spectra have been then
calculated and compared with experimental IR spectrum.
The assignment and characterization of theoretical vibra-
tional spectra were based on the potential energy distri-
bution analysis. This comparison has shown that the
theoretical spectrum for the dimer structure is in good
Keywords Naphthaleneacrylic acid Á Crystal structure Á
Density functional theory (DFT) calculation Á IR spectra Á
Hydrogen bonds
Introduction
The present study is connected with our research on the
nature of hydrogen bonds on spectral differences in car-
boxylic acid crystals. We investigated selected carboxylic
acid systems containing aromatic ring, for which the car-
boxyl groups in the molecules are being separated from
aromatic rings by a C=C double bond or methylene group.
Research on trans-cinnamic [1], benzoic [2], phenyla-
cetic [3], 1- and 2-naphthoic [4], 1- and 2-naphthylacetic
[5] acid crystals (Fig. 1), gave very interesting information
about influence of the electronic structure hydrogen-bon-
ded carboxylic acid molecules on polarized IR spectra in
the frequency ranges of the proton and deuteron stretching
vibration bands. Our results prove that separation of the
vibrating protons in the hydrogen bonds from the p-elec-
tron system by e.g. methylene group, is the main reason of
the differences observed in IR spectra of the investigated
compounds [3, 5].
´
A. Tyl (&) Á M. Jabłonska
Institute of Chemistry, University of Silesia, 9 Szkolna Street,
40-006 Katowice, Poland
e-mail: aleksandra.tyl@us.edu.pl
E. Chełmecka
Division of Statistics, Department of Instrumental Analysis,
´
Medical University of Silesia, 30 Ostrogorska Street,
41-200 Sosnowiec, Poland
Present Address:
´
M. Jabłonska
Institute of Environmental Engineering of the Polish Academy
of Sciences, 34M. Skłodowskiej-Curie Street,
41-819 Zabrze, Poland
In 1-naphthaleneacrylic acid [named also 3-(1-naph-
thyl)acrylic acid, systematic name: (E)-3-naphthalen-1-
ylprop-2-enoic acid], the carboxyl group is linked with
aromatic ring by styryl group. In this case, we expect similar
effects to those observed in IR spectra of trans-cinnamic acid
M. Nowak Á J. Kusz Á K. Pasterny Á R. Wrzalik
Insitute of Physics, University of Silesia, 4th Uniwersytecka
Street, 40-006 Katowice, Poland
123

326
Struct Chem (2012) 23:325–332
O
O
OH
OH
OH
OH
O
O
(III)
(IV)
(I)
(II)
O
OH
O
OH
O
O
OH
OH
(V)
(VI)
(VII)
(VIII)
OH
OH
OH
O
S
O
O
O
(XI)
(IX)
(X)
Fig. 1 The formulas of carboxylic acid systems: (I) 1-naphthalene-
acrylic acid, (II) trans-cinnamic acid, (III) benzoic acid, (IV)
phenylacetic acid, (V) 1-naphthoic acid, (VI) 2-naphthoic acid, (VII)
1-naphthylacetic acid, (VIII) 2-naphthylacetic acid, (IX) 3-(2-
furyl)acrylic acid, (X) trans-beta-2-thienylacrylic acid, (XI) 3,3-
dimethylacrylic acid
[1]. Thus, determination of 1-naphthaleneacrylic acid crystal
structure was indispensable for our spectral studies.
obtained with yield 37% (m.p. = 208 °C). Colourless
crystals suitable for X-ray analysis were grown from a
solution of ethanol and acetone (1:1 v/v) at room temper-
ature over a period of a few days in air.
1-naphthylacrylic acid and other acrylic acid derivatives
were recently evaluated [6] for their ability to inhibit the in
vitro activation of human complement. The investigations
have also shown that titled compound is not cytotoxic
towards mammalian cell lines. To shed more light on its
molecular structure and vibrational properties, detailed
molecular orbital calculations have been performed and
their results have been compared with experiment.
The IR spectra of the polycrystalline samples of the
1-naphthaleneacrylic acid and trans-cinnamic acid were
recorded on a Nicolet Magna 560 FT-IR spectrometer with
4 cm-1 resolution.
The X-ray experiment was performed at 150 K. For this
measurement, a colourless single crystal of the title com-
pound was mounted on a quartz glass capillary. The
measurement was performed with Oxford Diffraction KM4
kappa diffractometer equipped with a Sapphire3 CCD
detector and graphite-monochromated Mo Ka radiation
Experimental and computational methods
´
˚
3-(1-Naphthyl)acrylic acid was prepared by Doebner’s
condensation [7, 8] of 1-naphthaldehyde and malonic acid
(Scheme 1). A mixture of malonic acid (15 g, 144 mmol),
piperidine (1 mL, 10 mmol) and pyridine (25 mL,
310 mmol) was heated under reflux with stirring at 353 K.
After 30 min, 1-naphthaldehyde (4.4 mL, 32 mmol) was
added to the mixture. Then, the mixture was heating under
reflux for 5 h. Obtained yellow solution was freezing for
48 h at 255 K, filtered and soured by hydrochloric acid.
The resulting precipitate was purified by twice recrystalli-
zation from ethanol. After that white powder of (1) was
(k = 0.71073 A). Data collection, reduction, and correc-
tions were achieved using CrysAlis CCD, CrysAlis RED
[9].
During the data collection, x scans were performed. The
unit cell parameters were determined by least square
refinement of 2,080 reflections, 3.04 \ h \ 25°. The
structure was solved by direct method using SHELXS-97
[10] and refined by full-matrix least-squares procedure on
F2 with SHELXL-97 [10].
The hydrogen atoms were treated as riding on their
˚
parent atoms, with C–H = 0.95 A and with Uiso(H) = 1.2
123

Struct Chem (2012) 23:325–332
327
times Ueq(C). Hydrogen atoms involved in hydrogen
bonding were located in a difference Fourier map (DF) and
refined freely with isotropic displacement parameters.
Theoretical calculations of isolated 1-naphthylacrylic
acid molecule and two hydrogen-bonded molecules have
been carried out with the Gaussian 03 software package
[11] using density functional theory (DFT) at the B3LYP
level and with 6-31G(d, p) and 6-31 ? G(d, p) basis sets.
BSSE (basis set superposition error) effect has been taken
into consideration in the calculation. 1-naphthylacrylic acid
molecule can exist as different isomers due to the different
orientation around the double C=C bond. And, in addition,
each isomer can exist as different conformers due to the
hindered rotation around two single C1–C11 and C12–C13
bonds. First, we have regarded possible isomers, cis and
trans, according to orientation around C11=C12 bond.
Isomer trans is energetically more favourable than isomer
cis; the difference in energy is about 6 kcal/mol. Next, we
have investigated the dependence of the molecule energy
on the C9–C1–C11–C12 torsion angle. The rotational
Scheme 1 Synthesis of
1-naphthaleneacrylic acid
Fig. 2 a A view of the title
molecule, showing the atom
numbering scheme.
Displacement ellipsoids are
drawn at the 50% probability
level and H atoms are shown as
small spheres of arbitrary radii.
b Optimized structure and atom
numbering of 1-naphthylacrylic
acid dimer
123

328
Struct Chem (2012) 23:325–332
energy surface consists of four minima (two pairs). The
energy minimum corresponding to the angles -152.7° and
147.3° lies about 1.5 kcal/mol lower than the minimum
corresponding to the angles -32.7° and 27.3°. In the next
step, we have calculated the energy dependence on the
rotation around the C12–C13 bond. We have observed the
energy minimum for torsion angle C11–C12–C13–O1
equals -0.2 that correspond to an ideal synperiplanar
(‘cis’) (0°) geometry around C12–C13 bond. For compar-
ison, the energy of antiperiplanar (‘trans’) C12–C13
geometry is 1 kcal/mol higher. The geometry, corre-
sponding to the energy minimum, obtained according to the
procedure described above proved to be consistent with the
geometry obtained from the X-ray diffraction and has been
used as initial geometry for the further calculation of the
dimer.
The naphthalene ring of (1) is almost planar, the maxi-
˚
mum deviation of any of its atom is 0.0191 (13) A for C10,
˚
while the average deviation is 0.0121 A. The bond lengths
and angles (Table 2) correspond to those expected for the
atom types [14] and also with those of unsubstituted
naphthalene measured at 135 K [15]. Only within the C1
atom, the bonds are elongated and the angles are defor-
mated, which is connected with the presence of large
substituent in the a position. The satisfactory agreement
between calculated and experimental structural parameters
is observed; the dimer parameters are closer to experiment
than the corresponding monomer ones. In Table 3, the
greatest differences between monomer and dimer bond
lengths are visible for C13–O1 and C13–O2 interatomic
distances. The use of diffuse functions does not make a
significant difference in accuracy.
It is noteworthy that while in (1) the C1–C2 and C1–C9
bond lengths are quite different, 1.3859 (19) and 1.4486
˚
(19) A, respectively, that in the trans-cinnamic acid [16],
the corresponding bond lengths are similar [1.395 (2) and
Results and discussion
˚
1.401 (2) A]. In opposite to this, there are the differences
The asymmetric unit of (1) contains one 1-naphthaleneac-
rylic acid molecule. This compound crystallize in the form
of centrosymmetric hydrogen-bonded dimers (Fig. 2). The
experimental conditions are summarized in Table 1. The
data for publication were prepared with Shelx [10], Platon
[12] and Mercury [13] program packages.
between the C2–C1–C11 and C9–C1–C11 angles in both
acids—in (1) these angles are comparable [120.18 (14)°
and 121.12 (13)°, respectively], but in trans-cinnamic acid
they are significant differ [119.8 (1)° and 126.3 (1)°].
˚
Moreover, the C1–C11 = 1.481 (2) A bond in (1) is
˚
elongated towards the theoretical value (1.465 A) and the
˚
corresponding bond in trans-cinnamic acid (1.467 (2) A
[16]).
Table 1 Crystal data, structure solution methods and refinement
results for 1-naphthaleneacrylic acid
The naphthalene ring is not coplanar with the propenoic
group, the dihedral angle between the mean plane of the
naphthalene ring and the plane of the propenoic moiety is
11.11 (7)°. By comparison, the corresponding angles,
between the aromatic rings and the propenoic moiety, in
cinnamic acid [16], 3-(2-furyl)acrylic acid [17] and trans-
b-2-thienylacrylic acid (see Fig. 1) [18] are only about
6.3°, 5.18° and 3.63°, respectively. The only significant
differences between the calculated and the experimental
CCDC deposit no.
Empirical formula
Formula weight
Temperature (K)
Crystal system
Space group
715976
13H10O2
C
198.21
150 (2)
Monoclinic
C2/c
˚
a (A)
14.556 (3)
˚
b (A)
5.1332 (10)
26.832 (5)
˚
c (A)
Table 2 Selected geometrical parameters of the 1-naphthaleneacrylic
˚
b (°)
Volume (A )
97.02 (3)
3
˚
acid (A and °)
1989.8 (7)
Z
8
O1–C13
1.2453 (16)
1.3203 (16)
1.3858 (19)
1.4486 (19)
1.481 (2)
Calculated density (g/cm3)
Absorption coefficient (mm-1
Crystal size (mm)
1.323
O2–C13
)
0.09
C1–C2
0.56 9 0.09 9 0.02
2.8462–32.6796
5749/1711/0.028
1711/0/139
1.001
C1–C9
h range for data collection (°)
C1–C11
Reflection collected/unique/Rint
Data/restrains/parameters
Goodness of fit on F2
O1–C13–C12
C2–C1–C11–C12
C9–C1–C11–C12
O2–C13–C12
C11–C12–C13–O1
C11–C12–C13–O2
122.60 (14)
-12.1 (2)
169.37 (15)
114.82 (14)
4.0 (2)
Final R indices [I [ 2r (I)]
R indices (all data)
Largest peak and hole (eA-3
R1 = 0.0322, wR2 = 0.0584
R1 = 0.0594, wR2 = 0.0605
0.13 and -0.17
)
-175.90 (14)
123

Struct Chem (2012) 23:325–332
329
˚
˚
values are observed for the torsion angles C2–C1–C11–
C12 and C9–C1–C11–C12. The experimental angles are
-12.1° and 169.37°, while those calculated by the B3LYP/
6-31G** method are 26.3° and -155.4°, respectively.
The alkene-carbonyl conformation (C=C–C=O) is syn,
which is similar to the 2-propenoic acid [19] and to the
other mentioned above acids except trans-cinnamic acid
[16], where the conformation is anti. The substituents
affects also on the alkene-carbonyl torsion angle, which in
unsubstituted 2-propenoic acid is 0°. The value of this
angle increases when there is attached large group to the a
unsaturated carbon. For example, in dimethylacrylic acid
(see Fig. 1) [20, 21], 3-(2-furyl)acrylic acid [17], trans-b-
2-thienylacrylic acid [18], trans-cinnamic acid [16] and in
(1) the C=C–C=O torsion angles are about 0.5°, 3.99°,
5.49°, 177.17° and 4°, respectively. It is noteworthy that
from theoretical calculations the syn and anti conformers of
(1) were found to have comparable energies. The computed
C=C–C=O torsion angles for anti and syn conformers of
(1) are 179.668° and -0.333°, respectively.
[C13–O1 = 1.2453 A, C13–O2 = 1.3202 A] and the C–
C–O angles [C12–C13–O1 = 122.60°, C12–C13–O2 =
˚
114.82°] are different, the Dr and Du are 0.0749 A and
7.78°, respectively. It means that the carboxyl group is
ordered. By comparison, in 2-propenoic acid [19] the car-
˚
A and
boxyl group is also ordered (Dr = 0.0887
Du = 10.79°), but in trans-cinnamic acid [16] is only
partially ordered (Dr = 0.038 A and Du = 1.9°).
˚
There is only one independent molecule in the asym-
metric unit (Fig. 1). The molecule interact with molecule at
(1-x, -y, 1-z), via O–HÁÁÁO hydrogen bonds. This inter-
action leads to the formation of cyclic centrosymmetric
dimers, centred at (1/2, 0, 1/2), with the common motif
which is found in most other monocarboxylic acids,
namely R22(8) [22–25].
The crystal packing, viewed down the a axis, shows that
the dimers form layers that stack in the c direction and
form a zigzag pattern in the bc plane (Fig. 3). There are no
significant interactions between the dimers.
All the geometric parameters of O–HÁÁÁO interactions
(Table 4) observed in (1) fit into the limits for strong
hydrogen bonds defined by Desiraju and Steiner [26].
The theoretical investigation of hydrogen bonds was
The O–H group adopts a synplanar O=C–O–H confor-
mation, like most of carboxylic acids without intramolec-
ular O–HÁÁÁO hydrogen bonds [22]. The C–O bond lengths
Table 3 Comparison of
Experimental
6-31G(d, p)
monomer
6-31G(d, p)
dimer
6-31 ? G(d, p)
dimer
selected calculated geometry
parameters of 1-naphthylacrylic
acid with experiment
˚
Bond lengths (A)
C1–C11
1.481
1.336
1.471
1.245
1.320
1.465
1.346
1.477
1.217
1.360
1.465
1.346
1.473
1.237
1.326
1.464
1.343
1.472
1.231
1.326
C11–C12
C12–C13
C13–O1
C13–O2
Angles (°)
C9–C1–C11
C2–C1–C11
C1–C11–C12
C11–C12–C13
C12–C13–O1
C12–C13–O2
Dihedral angles (°)
C9–C1–C11–C12
C2–C1–C11–C12
C1–C11–C12–C13
C11–C12–C13–O1
C11–C12–C13–O2
Hydrogen bond geometry
O–H
121.1
120.6
120.4
126.4
120.0
126.3
111.5
120.6
120.3
126.4
120.7
123.3
112.8
120.5
120.4
126.3
120.8
123.7
112.8
120.2
127.7
121.6
122.6
114.8
169.4
-12.1
178.8
4.0
-154.6
27.0
-154.4
-153.3
27.2
28.3
-178.0
-0.5
-178.2
-178.3
-0.1
-0.1
-175.9
179.7
-179.8
-179.8
A/B
A/B
0.987
–
–
–
–
1.004/1.004
1.682/1.679
2.686/2.683
178.7/178.4
0.999/0.999
1.670/1.670
2.670/2.670
179.5/179.5
HÁÁÁO
1.664
2.646
OÁÁÁO
O–HÁÁÁO (°)
172.7
123

330
Struct Chem (2012) 23:325–332
Figure 4 presents also similarity between the IR spectra
in the range of the mO–H stretching vibration bands of the
1-naphtylacrylic and trans-cinnamic acids. There are some
differences between their structures, however, their hydro-
gen bond lengths and angles are very similar.
In Table 5, the assignment of the selected experimental
IR bands to the calculated vibrational frequencies, based on
the potential energy distribution (PED) analysis [29, 30], is
shown; the theoretical frequencies were scaled using the
common scaling factor, f = 0.965.
The most intense peak at 3004 cm-1 in the calculated
scaled dimer spectrum, assigned to the O–H–O hydrogen
bond stretching vibrations, corresponds to the experimental
broad band in the range 2800–3200 cm-1. Figure 5 pre-
sents the comparison of calculated IR spectra of isolated
molecule and 1-naphthylacrylic dimer with experimental
spectrum. In the case of the theoretical spectra, the calcu-
lated intensities were converted to Lorentzian bands with
5 cm-1 half-width. It is known that IR spectra of the
hydrogen-bonded dimers are fundamentally different from
the hydrogen bonds in monomer. The calculated IR spec-
trum for hydrogen-bonded dimer agrees much better with
experiment than that for the monomer. It can be seen that
the structure of the experimental spectrum has been quite
correctly reproduced in spite of the very simple scaling
procedure applied.
Fig. 3 A packing diagram of (1) viewed along the a axis. Symmetry
codes: (i) -x ? 1, -y, -z ? 1
Conclusions
performed at the B3LYP/6-31G** level of theory. Calcu-
˚
It was shown that the substituents affects also on the
conformation of the aromatic ring and of the propenoic
moiety. But when the carboxyl group is linked with aro-
matic ring by styryl group, the type of the aromatic ring do
not change the hydrogen bond geometry. The IR spectra of
1-naphtylacrylic and trans-cinnamic acids, in the range of
the mO–H stretching vibration bands, are very similar.
Theoretically predicted structural parameters appeared
to be in good agreement with the X-ray experimental ones.
The structure of the experimental IR spectrum has been
quite correctly reproduced by B3LYP/6-31G(d, p) calcu-
lations in spite of the very simple scaling procedure, using
one common scaling factor for all vibrations, applied. The
very good agreement between theoretical calculation and
experiment indicates that in the 1-naphthaleneacrylic
dimer, we have to do with two strong intermolecular
hydrogen bonds.
lated hydrogen-bond distances were O2ÁÁÁO1 = 2.655 A,
˚
˚
O2–H2O = 1.005 A, H2OÁÁÁO1 = 1.651 A and the calcu-
lated O2–H2OÁÁÁO1 angle was 178.2°. The energy of the
intermolecular hydrogen bonds was calculated and cor-
rected to basis set superposition error (BSSE) using a
standard procedure [27]. For the dimer, the total calcu-
lated energy of the hydrogen bonds was estimated at
-16.23 kcal/mol. This value indicates that regarding
hydrogen bonds are strong.
The strength of the hydrogen bond was also confirmed
by IR spectroscopy. From the polycrystalline spectrum of
(1) (Fig. 4), it can be seen that the mO–H stretching vibration
band is situated in the range 3100–2300 cm-1, with a shift
of about 900 cm-1 in relation to the band of the isolated
O–H stretching vibrations at 3650–3590 cm-1 [28].
Table 4 Hydrogen bond geometry for 1-naphthaleneacrylic acid
˚
(A and °)
D–HÁÁÁA
d(D–H)
d(HÁÁÁA)
d(DÁÁÁA)
\(DHA)
Supplementary material
O2–H2OÁÁÁOi 0.987 (17) 1.664 (17) 2.6458 (15) 172.7 (15)
Symmetry codes: (i) -x ? 1, -y, -z ? 1
Crystallographic data can be obtained from the Cambridge
Crystallographic Data Centre, by quoting the reference
123

Struct Chem (2012) 23:325–332
331
Fig. 4 The IR spectra of
1-naphthaleneacrylic acid and
trans-cinnamic acid measured
by the KBr pellet technique at
room temperature, showing the
mO–H frequency range
Table 5 Selected calculated and experimental vibrational frequen-
cies of 1-naphthylacrylic acid dimer
Experimentala Calculatedb Assignment PED([10%)c
dimer
3083 vw
3059 w
3048 m
3097
3093
64m(C–H)Ar B ? 12mC–H B; 63m(C–H)Ar A
? 12mC–H A
31m(C–H)Ar B ? 29m(C–H)Ar A
;
31m(C–H)Ar A ? 29m(C–H)Ar B
91m(C–H)Ar B; 91m(C–H)Ar A
50mO–HÁÁÁO A 50mO–HÁÁÁO B
57mO–HÁÁÁO B 49mO–HÁÁÁO A
32mC=O A ? 32mC=O B
3084
2995
2885
1697
1648
1682 vs
1626 m
23mC=O A ? 20mC=O B ? 12mC=C A
? 12mC=C B
1574 vw
1588
14mC–C(Ar) A ? 13mC–C(Ar) B;
14mC–C(Ar) B ? 13mC–C(Ar) A
1425 m
1350 w
1297 m
1227 w
975 w
1469
1357
1311
1161
990
24dO–H A ? 11mC–O A
15mC–C(Ar) A ? 15mC–C(Ar) B
12mC–O B ? 11mC–O A
Fig. 5 Comparison of B3LYP calculated scaled infrared spectrum of
1-naphthylacrylic acid dimer and monomer with experiment
10dC–H(Ar) A; 10dC–H(Ar) B
21cC–H A ? 17cC–H B; 21cC–H B
? 17cC–H A
number CCDC 715976. This data can be obtain free of
charge via www.ccdc.cam.ac.uk, or by contacting The
Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: ?44(0)1223-336033.
943 w
932
51cO–H A ? 29cO–H B
A and B denotes the corresponding part of the dimer in which the
given vibration is localized
a
Peak intensity: vs very strong, s strong, m medium, w weak, vw very
weak
b
Acknowledgement The authors gratefully acknowledge for enabled
performance of the calculations at the Academic Computer Centre
´
´
CYFRONET AGH of Krakow (grant No. MNiSW/SGI3700/SUM/
077/2008) and at WCSS Wrocław.
B3LYP/6-31G(d, p), scaled (f = 0.965)
c
Mode description: m stretching, d in-plane deformation, c out of
plane deformation
123

332
Struct Chem (2012) 23:325–332
12. Speak AL (2002) PLATON. University of Utrecht, Utrecht
13. Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP,
Taylor R, Towler M, van de Streek J (2006) J Appl Cryst 39:
453–457
14. Allen FA, Kennard O, Watson DG, Brammer L, Orpen AG,
Taylor R (1987) J Chem Soc Perkin Trans 2:S1–S19
15. Oddershede J, Larsen S (2004) J Phys Chem A 108:1057–1063
16. Wierda DA, Feng TL, Barron AR (1989) Acta Cryst C 45:
338–339
17. Danish M, Ali S, Mazhar M, Badshah A, Tiekink ERT (1995) Z
Kristallogr 210:703–704
18. Block S, Filippakis SE, Schmidt GMJ (1967) J Chem Soc B
233–238
References
´
1. Flakus HT, Jabłonska M (2004) J Mol Struct 707:97–108
2. Flakus HT, Chełmecki M (2002) Spectrochim Acta A 58:
179–196
3. Flakus HT, Chełmecki M (2002) Spectrochim Acta A 58:
1867–1880
4. Flakus HT, Chełmecki M (2003) J Mol Struct 659:103–117
5. Flakus HT, Chełmecki M (2004) J Mol Struct 705:81–89
6. Master HE, Khan SI, Poojari KA (2005) Bioorg Med Chem
13:4891–4899
7. Schulte-Frohlinde D, Bent DU (1974) Mol Photochem 6:315–320
8. Tanaka H, Takamuku S, Sakurai H (1979) Bull Chem Soc Jpn
523:801–806
¨
¨
19. Boese R, Blaser D, Steller I, Latz R, Baumen A (1999) Acta
Cryst C 55:IUC9900006
9. Diffraction Oxford (2006) CrysAlis CCD and CrysAlis RED,
version 1.171.29.2. Oxford Diffraction Ltd, Wrocław
10. Sheldrick GM (2008) Acta Crystallogr A64:112–122
11. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA,
Cheeseman JR, Montgomery JA Jr, Vreven T, Burant JC, Kudin
KN, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B,
Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada
M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M,
Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox
JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J,
Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R,
Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA,
Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels
AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghava-
chari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S,
Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P,
Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng
CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B,
Chen W, Wong MW, Gonzalez C, Pople JA (2004) GAUSS-
IAN03 revision B.04. Gaussian Inc, Pittsburgh
20. VECVEF – Private communication in CSD; Version 5.29
21. Allen FH (2002) Acta Cryst B 58:380–388
22. Leiserowitz L (1976) Acta Cryst B 32:775–802
23. Etter MC, MacDonald JC, Bernstein J (1990) Acta Cryst B
46:256–262
24. Bernstein J, Davis RE, Shimoni L, Chang NL (1995) Angew
Chem Int Ed Engl 34:1555–1573
25. Samuel Motherwell WD, Shields GP, Allen FH (1999) Acta
Cryst B 55:1044–1056
26. Desiraju GR, Steiner T (1999) The weak hydrogen bond in
structural chemistry and biology. Oxford University Press Inc,
New York
27. Boys SF, Bernardi F (1970) Mol Phys 19:553–566
28. Gu¨nzler H, Gremlich HU (2002) IR spectroscopy. Wiley,
Weinheim
29. Califano S (1976) Vibrational states. John Wiley & Sons, London
30. Baker J, Jarzecki AA, Pulay P (1998) J Phys Chem A 102:
1412–1424
123