Spectrochimica Acta Part A 75 (2010) 293–298

Contents lists available at ScienceDirect

Spectrochimica Acta Part A: Molecular and

Biomolecular Spectroscopy
journal homepage: www.elsevier.com/locate/saa

Crystal studies, vibrational spectra and non-linear optical properties of

l-histidine chloride monohydrate
A. Ben Ahmed a,∗ , H. Feki a , Y. Abid a , H. Boughzala b , C. Minot c
a
Laboratoire de Physique Appliquée (LPA), Faculté des Sciences 3018, BP802 Sfax, Tunisia
b
Laboratoire de cristallochimie Faculté des Sciences de Tunis, Tunisia
c
Laboratoire de Chimie Théorique (LCT), Université Pierre et Marie Curie, Paris VI, France

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

Article history: This paper presents the results of our calculations on the geometric parameters, vibrational spectra and
Received 3 June 2009 hyperpolarizability of a non-linear optical material l-histidine chloride monohydrate. Due to the lack of
Received in revised form 3 October 2009 sufficiently precise information on geometric parameters available in literature, theoretical calculations
Accepted 13 October 2009
were preceded by re-determination of the crystal X-ray structure. Single crystal of l-histidine chloride
monohydrate has been growing by slow evaporation of an aqueous solution at room temperature. The
Keywords:
compound crystallizes in the non-Centro-symmetric space group P21 21 21 of orthorhombic system. IR
l-Histidine
spectrum has been recorded in the range [400–4000 cm−1 ]. All the experimental vibrational bands have
NLO
Hyperpolarizability
been discussed and assigned to normal mode or to combinations on the basis of our calculations. The opti-
DFT mized geometric bond lengths and bond angles obtained by using DFT//B3LYP/6-31G (d) method show
TD-DFT a good agreement with the experimental data. The calculated vibrational spectra are in well agreement
with the experimental one. To investigate microscopic second-order non-linear optical NLO behavior
of the examined complex, the electric dipole , the polarizability ˛ and the hyperpolarizability ˇ were
computed using DFT//B3LYP/6-31G (d) method. The time-dependent density functional theory (TD-DFT)
was employed to descript the molecular electron structure of the title compound using the B3LYP/6-31G
(d) method. According to our calculations, l-histidine chloride monohydrate exhibits non-zero ˇ value
revealing microscopic second-order NLO behavior.
© 2009 Elsevier B.V. All rights reserved.

1. Introduction theoretical calculations on the structure and vibrational spectra of

The development and focus on new materials possessing non-
linear optical properties have been diverted from traditional
inorganic solids such as LiNbO3 and KH2 PO4 to organic and inor-
ganic systems due to numerous reasons [1]. In fact, considerable
efforts have been made to combine amino acid with various inter-
esting organic and inorganic matrices to produce materials having
a non-Centro-symmetric cell, large polarizability and a strong
non-linear optical coefficient. However, in conjunction with some
recent work on these compounds [2–5], the crystal structure and
vibrational spectra of l-histidine oxalate, l-histidine bromide and
l-histidinium dihydrogen phosphate–phosphoric acid have been
investigated in our laboratory [6–8]. In the previous study, the
crystal structure of l-histidine chloride monohydrate has been pub-
lished by various authors ODA et al. [9], Fuess et al. [10] and Dietmar
et al. [11]. To the best of our knowledge, experimental data on
geometric parameters and especially that of hydrogen bonds and
∗ Corresponding author. Tel.: +216 96 933 658.
E-mail address: ahmedlpa@yahoo.fr (A.B. Ahmed).
l-histidine chloride monohydrate are not available in the literature.
Then, for a proper comparison with our theoretical calculations, the
re-determination of the crystal structure is essential. In this work,
we report X-ray and IR spectroscopy study of l-histidine chloride
monohydrate. To obtain a more reliable assignment of the experi-
mental bands, we have calculated the vibrational frequencies in the
ground states using DFT method. The non-linear optical properties
are also addressed theoretically. The electric dipole moment tot ,
the isotropic polarizability ˛tot and the first hyperpolarizability ˇtot
of the title compound are calculated.
2. Experimental
2.1. Preparation
l-Histidine chloride monohydrate crystal was produce from
aqueous solution with equimolar proportion of l-histidine (purity
99%) and hydrochloric acid. The synthesized compound was dis-
solved in doubly distilled water using a magnetic stirrer and filtered
twice to remove the suspended impurities in the solution. Two
weeks later, transparency crystals were obtained.

1386-1425/$ – see front matter © 2009 Elsevier B.V. All rights reserved.
doi:10.1016/j.saa.2009.10.026
294 A.B. Ahmed et al. / Spectrochimica Acta Part A 75 (2010) 293–298

Table 1
Crystal data and structure refinement for l-histidine chloride
monohydrate.

Empirical formula C6 H12 N3 O3 Cl

Formula weight (g/mol) 209.64
Temperature (K) Room temp. (293–303)
Crystal system Orthorhombic
Space group P21 21 21
a (Å) 6.848 (2)
b (Å) 8.924 (3)
c (Å) 15.298 (5)
˛ (◦ ) 90
ˇ (◦ ) 90
␥ (◦ ) 90
Volume (Å3 ) 934.885 (5)
Z 4
D calc (g cm−1 ) 1.489
 (mm−1 ) 3.897
Crystal color/habit Colorless/prism
R-factor (%) 3.62

2.2. Crystal structure determination

The experiment was carried out on a parallelepiped single crys-

tal using Enraf-Nonus C4D4 four circle diffractometer with Mo K␣
radiation. The crystal structure was solved by direct methods using
SHELXS-97. Full-matrix F2 least-squares refinement and subse-
quent Fourier synthesis procedures were performed by SHELXL-97.
Successive refinements based on F2 leads to a reliability factors
of R = 0.0362. Anisotropy thermal displacement parameter refine-
ment was used for all non-hydrogen atoms. The crystal data and
structure solution and refinement details are given in Table 1.

2.3. Spectroscopic measurements

Infrared spectroscopy is effectively used to identify the func-

tional groups and to determine the molecular structure of the
synthesized compound. In order to analyze qualitatively the pres-
ence of functional groups in l-histidine chloride monohydrate,
FT-IR spectrum was recorded using Bruker FT-IR Spectrometer by
KBr pellet technique in the range 400–4000 cm−1 (Fig. 3).

2.4. Computational details

The geometries were fully optimized without any constraint

with the help of analytical gradient procedure implemented within
Gaussian 98 program [12]. All the parameters were allowed to
relax and all the calculations converged to an optimized geome-
try which corresponds to a true energy minimum revealed by the
lack of imaginary values in the wave numbers calculations. Vibra-
tional frequencies are calculated with B3LYP/6-31G (d) and then
scaled by 0.963 [13]. Vibrational mode assignments were made by
visual inspection of modes animated by using the Molekel program
[14] and also with the results reported for similar compounds. On
the other hand, the time-dependent density functional theory (TD-
DFT) at the B3LYP/6-31G (d) level was employed to determine and
analysis the electronic spectrum.
3. Results and discussions
3.1. Structure description
X-ray diffraction analysis has revealed that the title compound
crystallizes in orthorhombic system with space group P21 21 21 . The
unit cell dimensions are a = 6.848 (2) Å, b = 8.924 (3) Å, c = 15.298
(5) Å and V = 934.88 (5) Å3 . These results agree with that found
by various authors [9–11]. The atom-numbering scheme for l-
histidine chloride monohydrate is shown in Fig. 1. The reduced
Fig. 1. Atom-numbering scheme for of l-histidine chloride monohydrate. (a) The
experimental results and (b) the optimized geometry.
atomic coordinates are listed in Table 2. Selected measured bonds
lengths and bonds angles together with the calculated ones are
grouped in Table 3. The crystal structure consists of l-histidinium
cations, chloride anions and H2 O molecules connected by nine
hydrogen bonds (Table 4). The crystal data confirm that the l-
histidine cation occurs in the zwitterions form, with additional
protonation of the N(2) and N(3) ring atoms. The structure reveals
also that a chloride anion is joined with three l-histidine cation and
a water molecule through six hydrogen bonds. Description of the
structure which reflects the various hydrogen bonds are given in
Fig. 2. As shown in Table 3, the optimized parameters are in well
agreement with the experimental data and the largest discrepan-
cies do not exceed 3.41%. This discrepancies can be explained by
the fact that the calculation relates to the isolated molecule where
 A.B. Ahmed et al. / Spectrochimica Acta Part A 75 (2010) 293–298
Fig. 2. Molecular arrangement of L-histidine chloride monohydrate. The hydrogen bonds are shown as the dashed lines (view along a direction).
the intermolecular Coulombic interaction with the neighboring
molecules are absent, whereas the experimental result corresponds
to interacting molecules in the crystal lattice. The largest dis-
crepancies between the calculated and experimental geometrical
parameters are observed for X–H (X = C, N). Since large deviation
from experimental X–H bonds may arises from the low scattering
factors of hydrogen atoms in the X-ray diffraction experiment we
did not discuss C–H and N–H bonds lengths.
3.2. Vibrational study
To the best of our knowledge, any theoretical vibrational study
made on the title compound was found in the literature. Then, we
have calculated the vibrational spectra (Figs. 4 and 5) of l-histidine
chloride monohydrate by using DFT method with 6-31G (d) basis
set. The frequencies of the calculated and observed bands are pro-
vided in Table 5. The vibration of l-histidine cation and chloride
anion appear in the 400–4000 cm−1 frequency range. As it can be
seen from Table 5 a noticeable difference between the experimental
and the calculated frequencies associated to the N–H, C–H, C=O and
C–N stretching were found. Such discrepancies were reported in the
literature [2,7,8,15]. In fact, the bands at 3444 and 3412 cm−1 are
295
assigned to the O–H asymmetric and symmetric stretching of water
molecule respectively. These modes are calculated at 3506 and
3455 cm−1 for B3LYP. The bands at 3157 and 3108 cm−1 , calculated
at 3252 and 3177 cm−1 , are assigned respectively to the asymmet-
ric and symmetric N–H stretching. Two peaks observed in the IR
spectrum in the region 3050–2900 cm−1 . These are usual range
of appearance for asymmetric and symmetric stretching modes
of –(CH2 )– groups. As it can be seen from Table 5 the calculated
values of these modes (as (CH2 ) and s (CH2 )) are not sensitive
to the environment. Note that the lack of any strong bands at
1700 cm−1 in IR spectrum clearly indicate that l-histidine posses
carboxylic group COO− in l-histidine chloride monohydrate crys-
tal. A detailed assignment of observed bands is given in Table 5.
According to the X-ray data (Table 4), there are 9 hydrogen bonds
in the crystal. They include the O–H· · ·O type with lengths of 2.75 Å.
The hydrogen bonds length of the N–H· · ·O type range from 2.77
to 2.83 Å, while the N–H· · ·Cl and C–H· · ·Cl types extends from
3.18 to 3.36 Å and 3.37 to 3.53 Å respectively. The weak IR band
located at 1122 cm−1 calculated at 1138 is assigned to the set of
weak interactions including N–H· · ·Cl. The weak IR band located
at 3157 cm−1 is assigned to the set of weak interactions including
N–H· · ·O.
296 A.B. Ahmed et al. / Spectrochimica Acta Part A 75 (2010) 293–298

Table 2
The reduced atomic coordinates in the structure of l-histidine chloride
monohydrate.

Atom x/a y/b z/c

Cl1 0.21978 (8) 0.47751 (6) 0.42567 (4)

O1 0.14408 (3) 0.98685 (2) 0.32959 (2)
O2 0.21051 (3) 1.06603 (2) 0.46465 (2)
O3 0.84010 (3) 1.34862 (3) 0.33136 (2)
N1 0.53224 (3) 1.21275 (2) 0.41917 (2)
N2 0.63726 (3) 0.67510 (2) 0.41953 (2)
N3 0.81093 (3) 0.85423 (2) 0.36664 (2)
C1 0.81786 (4) 0.72439 (3) 0.40961 (2)
C2 0.24390 (3) 1.05649 (2) 0.38565 (2)
C3 0.50970 (3) 0.77439 (2) 0.38172 (2)
C4 0.56132 (3) 1.02586 (3) 0.29910 (2)
C5 0.61785 (3) 0.88815 (2) 0.34879 (2)
C6 0.42574 (3) 1.13352 (2) 0.34881 (2)
H1 0.94276 (5) 0.67417 (4) 0.42750 (2)
H2 0.60784 (5) 0.58925 (4) 0.44527 (2)
H3 0.36791 (4) 0.76176 (3) 0.38051 (2)
H4 0.92082 (4) 0.91403 (3) 0.35467 (2)
H5 0.67901 (4) 1.08278 (3) 0.28183 (2) Fig. 3. Measured IR spectrum of L-histidine chloride monohydrate in the region
H6 0.49419 (5) 0.99801 (4) 0.24888 (2) 400–4000 cm−1 .
H7 0.38094 (4) 1.21218 (3) 0.30896 (2)
H8 0.45144 (4) 1.28214 (4) 0.43871 (2)
H9 0.63267 (5) 1.25881 (4) 0.39552 (2) 3.3. Hyperpolarizability calculation
H10 0.57310 (5) 1.15171 (4) 0.46172 (2)
H11 0.95160 (7) 1.37721 (5) 0.35653 (3) As mentioned above, this study is extended to the determination
H12 0.85504 (8) 1.37916 (5) 0.27795 (3) of the electric dipole moment tot , the isotropic polarizability ˛tot
and the first hyperpolarizability ˇtot of the title compound.
Table 3 Since the values of the polarizability ˇ and the first hyperpolar-
Comparison between observed and calculated inter-atomic parameters of l- izability ˇ of Gaussian 98 output are reported in atomic units (a.u.),
histidine chloride monohydrate. the calculated values have been converted into electrostatic units
Parameters Observed Calculated  (%) (esu) (˛: 1 a.u. = 0.1482 × 10−24 esu; ˇ: 1 a.u. = 8.6393 × 10−33 esu.
Bonds length (Å)
Table 6 listed the B3LYP/6-31G (d) results of the electronic dipole
O1–C2 1.26 (2) 1.26 0 moment i (i = x, y, z), polarizability ˛ij and the first hyperpolar-
O2–C2 1.23 (2) 1.23 0 izability ˇijk for l-histidine chloride monohydrate. The calculated
N1–C6 1.48 (2) 1.50 1.33 dipole moment is equal to 14.31 D (Debay). The highest value
N2–C1 1.32 (3) 1.34 1.49
of dipole moment is observed for component y . In this direc-
N2–C3 1.37 (2) 1.38 0.72
N3–C1 1.33 (3) 1.32 0.75 tion, this value is equal to 11.51 D. For direction x and z, these
N3–C5 1.38 (2) 1.38 0 values are equal to 8.50 D and −0.0260 D respectively. The calcu-
C2–C6 1.52 (2) 1.54 1.29 lated polarizability ˛tot , is equal to 12.96 × 10−24 esu. As we can
C3–C5 1.35 (2) 1.37 1.45 see in Table 6, the calculated polarizability ˛ij have non-zero val-
C4–C5 1.49 (2) 1.49 0
ues and was dominated by the diagonal components. The first
C4–C6 1.53 (2) 1.53 0
hyperpolarizability value ˇtot of the title compound is equal to
Bonds angles (◦ )
31.97 × 10−31 esu. The hyperpolarizability ˇ dominated by the lon-
C1–N2–C3 109.42 (0) 108.97 0.41
C1–N3–C5 108.76 (0) 109.87 1.01
gitudinal components of ˇxxx , ˇyyy , ˇxxy and ˇxyy . Domination of
N2–C1–N3 108.22 (0) 108.05 0.15 particular components indicates on a substantial delocalization of
O1–C2–O2 126.90 (0) 129.08 1.68 charges in these directions. In directions of ˇzzz , ˇyyz, ˇxzz , ˇxyz ,
O1–C2–C6 114.34 (0) 113.06 1.11
O2–C2–C6 118.75 (0) 114.85 3.28
N2–C3–C5 107.03 (0) 106.82 0.19
C5–C4–C6 114.73 (0) 116.79 1.76
N3–C5–C3 106.57 (0) 106.27 0.28
N3–C5–C4 121.82 (0) 123.51 1.36
C3–C5–C4 131.57 (0) 130.21 1.10
N1–C6–C2 110.35 (0) 108.89 1.32
N1–C6–C4 111.15 (0) 114.83 3.20
C2–C6–C4 113.14 (0) 109.28 3.41

Table 4
Hydrogen-bonding geometries for l-histidine chloride monohydrate.

D–H· · ·A D–H (Å) D· · ·A (Å) H· · ·A (Å) D–H· · ·A (◦ )

O3–H12· · ·O1 0.867 (5) 2.756 (3) 1.905 (5) 166.47 (4)
O3–H11· · ·Cl 0.892 (5) 3.188 (2) 2.300 (5) 173.04 (4)
N1–H9· · ·O3 0.879 (4) 2.778 (3) 1.903 (4) 173.14 (3)
N1–H10· · ·Cl 0.894 (3) 3.188 (2) 2.304 (3) 170.51 (3)
N1–H8· · ·Cl 0.883 (3) 3.189 (2) 2.366 (3) 155.36 (3)
N2–H2· · ·Cl 0.885 (4) 3.360 (2) 2.854 (4) 117.89 (3)
N2–H2· · ·O2 0.885 (4) 2.832 (2) 2.077 (4) 142.76 (3)
C1–H1· · ·Cl 1.004 (3) 3.534 (2) 2.584 (4) 157.79 (3)
C3–H3· · ·Cl 0.978 (3) 3.378 (2) 2.818 (3) 117.17 (2) Fig. 4. Calculated IR spectrum of l-histidine chloride monohydrate in the region
400–4000 cm−1 .
 A.B. Ahmed et al. / Spectrochimica Acta Part A 75 (2010) 293–298 297

Table 6
The electric dipole moment  (D) the average polarizability ˛tot (×10−24 esu) and
first hyperpolarizability ˇtot (×10−31 esu) for l-histidine chloride monohydrate.

x 8.50 ˇxxx 19.10

y 11.51 ˇyyy 15.93
z −0.02 ˇzzz −0.88
 14.31 ˇxyy 2.03
˛xx −16.90 ˇxxy 5.51
˛yy −9.83 ˇxxz 1.28
˛zz −12.17 ˇxzz 1.22
˛xy 1.48 ˇyzz 1.39
˛xz −0.18 ˇyyz −1.11
˛yz −0.51 ˇxyz 0.45
˛tot 12.96 ˇtot 31.97

Table 7
Comparison of the dipole moment, the polarizability, the first hyperpolarizability
for l-histidine and l-histidine chloride monohydrate.

Compounds  (D) ˛tot (×10−24 esu) ˇtot (×10−31 esu) EH-L (eV)

l-Histidinium(+1) 11.82 6.32 13.37 5.05

l-histidine chloride 14.31 12.96 31.97 3.13
monohydrate

ˇxxz , and ˇyzz the values of components are relatively medium. In

other directions, the particular components are practically equal
to 0. In order to test the effect of hydrogen bonds we have calcu-
lated tot , ˛tot , and ˇtot of l-histidinium (+1) cation. As listed in
Table 7, the value of ˛tot for l-histidine chloride monohydrate is
predicted about twice larger than that of l-histidinium (+1) while
the increment of ˇtot is about 2.39 times than for the corresponding
one of l-histidinium (+1). This clearly indicates that in acid–base
hybrid crystals, hydrogen bonds play an important role not only
in the creation of crystal structure and its stability, but also in the
Fig. 5. Calculated Raman spectra of l-histidine chloride monohydrate in two regions enhancement of the polarizability ˛ and the hyperpolarizability ˇ
(a) 200–1800 cm−1 and (b) 2900–3600 cm−1 .
of the crystal. Similar result has been observed in our previous
studies [7,8]. To understand this phenomenon in the context of
molecular orbital, we examined the molecular HOMOs and molec-
ular LUMOs generated via Gaussian 98. The calculated energies
gaps are listed in Table 7. As it can be seen, the compound hav-
ing the higher ˇtot value, correspond to the low HOMO–LUMO
Table 5 energy gap. This result indicates that intermolecular hydrogen
Observed and calculated frequencies (cm−1 ) of l-histidine chloride monohydrate.
bonds have a substantial influence on the first hyperpolarizabil-
Calculated Observed Assignment ity. It is well-known that the decrease of the gap energy EH-L
Raman IR FT-IR FT-Raman [16]
would enhance the second-order NLO properties. Then, in order
to compare the NLO properties of l-histidine chloride monohy-
3506 – 3444 – O–H asym. stretching of water
drate with other similar compounds, we have calculated EH-L
3403 3455 3412 – O–H sym. stretching of water
3252 – 3157 – N–H asym. stretching of the KDP, l-histidine bromide and l-histidinium dihydrogen
3173 3177 3108 – N–H sym. stretching phosphate–phosphoric acid. As can be seen in Table 8, the energy
3056 3066 3021 – CH2 asym. stretching gap between HOMO and LUMO of l-histidine chloride monohydrate
2961 2948 2934 – CH2 sym. stretching (EH-L = 3.13 eV) is lowers than that of KDP (EH-L = 4.82 eV), l-
1673 1679 1637 1650 C = O stretching
– 1658 1607 1600 H2 O deformation
histidine bromide (EH-L = 4.20 eV) and L-histidinium dihydrogen
1614 – 1583 – NH3 + stretching phosphate–phosphoric acid (EH-L = 3.81 eV). On the other hand, as
1516 1499 1496 1485 C–N stretching it can be seen from Table 8, the title compound presents the lowest
1472 1471 1431 1450 Ring deformation calculated absorption wavelength involving a good transparency in
1445 1442 1414 – N–H bending
visible region. Thus, it has been conclude that l-histidine chloride
1382 1380 1335 1360 CH2 deformation
1309 1344 1309 1317 C–N stretching monohydrate displays large second-order NLO properties.
1293 1291 1286 1264 C–C and C=O stretching
1202 – 1185 1161 C–H in plane bend and C–C stretch
1173 – 1141 1145 C–H in plane bending Table 8
1138 – 1122 – N–H bending Comparison the first hyperpolarizability for l-histidine chloride monohydrate and
1080 – 1079 1068 C–H in plane bending others NLO compounds.
1004 1002 976 – N–H bending
Compounds  (nm) EH-L (eV) ˇtot (×10−31 esu)
953 – 916 – C–H out of plane bending
882 878 866 824 C–N deformation Reference materiel (KDP) 299 4.82 6.85
831 826 822 809 Ring deformation l-histidine bromide 350 4.20 16.75
735 743 696 697 C = O deformation l-histidinium dihydrogen 395 3.81 24.99
657 649 630 – Ring deformation phosphate–phosphoric acid
570 – 528 532 C–C deformation l-histidine chloride monohydrate 225 3.13 31.97
298 A.B. Ahmed et al. / Spectrochimica Acta Part A 75 (2010) 293–298
4. Summary
In this work we have calculated the geometric parameters, the
vibrational frequencies and the non-linear optical properties of
l-histidine chloride monohydrate by using DFT (B3LYP) method.
The theoretical calculations were preceded by re-determination of
the crystal X-ray structure. Single crystal of l-histidine chloride
monohydrate has been growing by slow evaporation of an aque-
ous solution at room temperature. The compound crystallizes in
the non-Centro-symmetric space group P21 21 21 of orthorhombic
system. The theoretical IR and Raman spectrum have been simu-
lated. All the experimental vibrational bands have been discussed
and assigned to normal mode or to combinations on the basis of our
calculations. Non-linear optical NLO behavior of the examined com-
plex was investigated by the determination of the electric dipole
moment , the polarizability ˛ and the first hyperpolarizability
ˇ using the DFT//B3LYP/6-31G(d) method. The value of ˛tot for
l-histidine chloride monohydrate is predicted about twice larger
than that of l-histidinium (+1) while the increment of ˇtot is about
2.39 times than for the corresponding one of l-histidinium (+1).
This clearly indicates that in acid–base hybrid crystals, hydrogen
bonds play an important role not only in the creation of crystal
structure and its stability, but also in the enhancement of the polar-
izability ˛ and the hyperpolarizability ˇ of the crystal. The energy
gap between HOMO and LUMO of l-histidine chloride monohydrate
is lower than that of KDP, l-histidine bromide and l-histidinium
dihydrogen phosphate–phosphoric acid. In summary, l-histidine
chloride monohydrate displays large second-order NLO proper-
ties.
References
[1] M.D. Aggarwal, J. Stephens, A.K. Batra, R.B. Lal, J. Optoelectron. Adv. Mater. 5
(2003) 555.
[2] A. Joseph Arul Pragasam, S. Selvakumar, K. Thamizharasan, D. Prem Anand, P.
Sagayaraj, Cryst. Growth 280 (2005) 271.
[3] S. Dhanuskodi, J. Ramajothi, Cryst. Res. Technol. 39 (2004) 592.
[4] M.K. Marchewka, S. Debrusb, A. Pietraszko, A.J. Barnes, H. Ratajczak, J. Mol.
Struct. 656 (2003) 265.
[5] S. Gokul Raj, G. Ramesh Kumar, R. Mohan, S. Pandi, R. Jayavel, J. Mater. Chem.
Phys. 90 (2005) 144.
[6] T. Dammak, N. Fourati, Y. Abid, H. Boughzala, A. Mlayah, C. Minot, Spectrochim.
Acta Part A 66 (2007) 1097.
[7] A. Ben Ahmed, H. Feki, Y. Abid, H. Boughzala, A. Mlayah, J. Mol. Struct. 888
(2008) 180.
[8] A. Ben Ahmed, H. Feki, Y. Abid, H. Boughzala, A. Mlayah, C. Minot, J. Mol. Struct.
920 (2009) 1.
[9] K. Oda, H. Koyama, Acta Cryst. B28 (1972) 639.
[10] H. Fuess, D. Hohlwein, S.A. Mason, Acta Cryst. B33 (1977) 654.
[11] D. Hohlwein, Acta Cryst. A33 (1977) 649.
[12] M.J. Frish, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman,
V.G. Zakrzewski, J.A. Montgomery, J.R.E. Stramann, J.C. Burant, S. Dapprich, J.M.
Millam, A.D. Daniels, K.N. Kudin, M.C. Stain, O. Farkas, J. Tomasi, V. Barone, M.
Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski,
G.A. Petersson, P.Y. Agula, Q. Cui, K. Morkuma, D.K. Malick, A.D. Rabuck, K.
Raghavachri, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov,
G. Liv, A. Liashenko, P. Piskorz, I. Komaromi, R. Comperts, R.L. Martin, D.J. Fox, T.
Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkaray, M. Challacombe, P.M.W. Gill,
B. Johnson, W. Chen, M.W. Wang, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S.
Replogle, J.A. Pople, Gaussian 98, Revision A. 9, Gaussian, Inc., Pittsburgh, PA,
1998.
[13] G. Rauhut, P. Pulay, J. Phys. Chem. 99 (1995) 3093.
[14] P. Flukiger, H.P. Luhti, S. Portmann, J. Weber, Molekel 4.2, Swiss Center for
Scientific Computing, Manno, Switzerland, 2000–2002.
[15] T. Vijayakumar, I. Hubert Joe, C.P. Reghunadhan Nair, V.S. Jayakumar, J. Mol.
Struct. 877 (2008) 20.
[16] V. Kannan, R. Bairava Ganesh, P. Ramasamy, Cryst. Growth Des. 6 (2006) 1876.