Experimental and theoretical studies of the triphenyltin(IV) chloride adduct of pyridine-2-ethanol

Article abstract of DOI:10.1016/j.molstruc.2009.08.010

In this paper, we have reported adduct complex structure of triphenyltin(IV) chloride and pyridine-2-ethanol as a novel triorganotin complex, which was prepared by the reaction of Ph₃SnCl with pyridine-2-ethanol. The complex was characterized b

Full text of DOI:10.1016/j.molstruc.2009.08.010

Journal of Molecular Structure 937 (2009) 44–49
Contents lists available at ScienceDirect
Journal of Molecular Structure
journal homepage: www.elsevier.com/locate/molstruc
Experimental and theoretical studies of the triphenyltin(IV) chloride adduct
of pyridine-2-ethanol
Ali R. Salimi a, Masoud Mirzaei a, Mohammad Chahkandi a, Amirreza Azadmeher b,
Hossein Eshtiagh-Hosseini a, Hamid R. Khavasi b, Mostafa M. Amini b,
*
a Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad 917791436, Iran
b Department of Chemistry, Shahid Beheshti University, G.C., Tehran 1983963113, Iran
a r t i c l e i n f o
a b s t r a c t
Article history:
Received 9 July 2009
Received in revised form 8 August 2009
Accepted 11 August 2009
Available online 15 August 2009
In this paper, we have reported adduct complex structure of triphenyltin(IV) chloride and pyridine-2-eth-
anol as a novel triorganotin complex, which was prepared by the reaction of Ph3SnCl with pyridine-2-eth-
anol. The complex was characterized by elemental analysis, mass spectrometry, and IR, 1H, 13C and 119Sn
NMR spectroscopies. The molecular structure was determined by single crystal X-ray analysis. Complex
adapts trigonal–bipyramidal geometry with trigonality index
s = 0.88; the phenyl substituents on tin
occupying the equatorial positions and the oxygen and chlorine atoms taking up the axial positions.
DFT calculations of adduct complex compound of triphenyltin(IV) chloride and pyridine-2-ethanol ligand
as a monomeric and dimeric forms at the B3LYP/6-31G (d, p) level using effective core potential with con-
sideration of relativistic effects for stannous have been performed. Theoretical investigation of dimeric
form of complex, which exists in the crystal structure, shows the stabilization role of intermolecular
hydrogen bonding in this system.
Keywords:
Triorganotin complex
X-ray crystal structure
Hydrogen bonding
Theoretical calculations
Ó 2009 Elsevier B.V. All rights reserved.
1. Introduction
from the other moieties into oxygen atoms of H2O by polar hydro-
gen bonding can increase the basicity of oxygen atom until it can
Hydrogen bond formation is often the key interaction in both
intramolecular and intermolecular contacts. Its understanding
carries the potential of correlating structure with chemical proper-
ties and it may provide opportunity to design molecules with
desired characteristics. The presence of hydrogen bonding interac-
tions can play an important role in stabilizing of many biological
and chemical systems. Researching into hydrogen-bonded molecu-
lar clusters is crucial with a view to understanding a wide variety
of chemical and biochemical processes. Hydrogen bonding and in
effect, anomalous physical and chemical properties have been
extensively studied both theoretically and experimentally [1–4].
Organotin compounds, which are amongst the most widely
used organometallic compounds, because of industrial and agricul-
tural applications in general and di- and triorganotin containing
Sn–O bonds in particular continues to grow, are very focus of
attention [5–7]. Donor ligands such as carboxylate group, water
and alkoxide molecules can provide coordinated oxygen to tin cen-
ter [8–10]. X-ray crystal structure investigations of several aqua
complexes of di- and triorganotin(IV) compounds has demon-
strated the basic behavior of hydrogen bonding in formation of cor-
responding complexes. In fact, the pumping of electron density
easily coordinate to tin center. This has been observed in the
crown–ether complex of {[(CH3)2SnCl2ÁH2O]18-crown-6}n previ-
ously [11]. In this paper, similar to above verified evidence, in a
new synthesized triphenyltin(IV) complex of pyridin-2-ethanol,
[Ph3SnCl(HOC7H9N)], hydrogen bonding has been investigated in
which pyridin-2-ethanol retains the hydrogen atom of alcohol
and oxygen of hydroxyl group act as a ligand in complex formation.
In fact, the existence of hydrogen atom engaged in the intermolec-
ular hydrogen bonding forms the stable dimmer of complex. The
role of this hydrogen bonding as an important factor in the stabil-
ization of structure has been considered at the density functional
level of theory (DFT). All calculations were performed using the hy-
brid exchange–correlation functional B3LYP method.
2. Experimental
2.1. Materials and physical measurements
Triphenyltin(IV) chloride and pyridine-2-ethanol were pur-
chased from Merck and used without further purification. Melting
point was obtained with Electrothermal 9200 melting point appa-
ratus and was not corrected. Infrared spectrum from 4000 to
400 cmÀ1 was recorded on a Shimadzu 470 FT-IR instrument, using
KBr pellets. 1H, 13C and 119Sn NMR spectra were recorded at room
* Corresponding author. Tel.: +98 21 22431661; fax: +98 21 22431663.
E-mail address: m-pouramini@cc.sbu.ac.ir (M.M. Amini).
0022-2860/$ - see front matter Ó 2009 Elsevier B.V. All rights reserved.
doi:10.1016/j.molstruc.2009.08.010

A.R. Salimi et al. / Journal of Molecular Structure 937 (2009) 44–49
45
Table 1
colorless crystals. Anal. Calc. for C25H24ONClSn: C, 59.04; H, 4.76; N,
2.75. Found: C, 58.82; H, 4.83; N, 2.49. IR (KBr, cmÀ1): 477(m),
504(w), 576(w), 695(s), 732(s), 765(m), 1007(m), 1049(m),
1077(m), 1430(s), 1480(m), 1596(m), 1634(b), 2923(w), 3048(w),
Crystal data for title compound.
Formula
Formula wt.
Crystal size
Crystal system
Space group
T (K)
a (Å)
b (Å)
c (Å)
C25H24ClNOSn
508.61
0.50 Â 0.40 Â 0.18
Monoclinic
P21/c
3
3422(s). 1H NMR (CDCl3, ppm): 2.13 (2H, t, CH2, JH–H, 7.5 Hz), 2.3
3
(2H, t, CH2, JH–H, 7.5), 7.2–7.7 (19H, m, C6H5 and C5H4N), 8.5 (1,
OH). 13C NMR (CDCl3, ppm): 38.7 (CH2), 61.8 (CH2), 121.6 (C,
293 (2)
10.0375 (11)
10.6965 (10)
21.608 (3)
97.233 (10)
2301.5 (4)
4
1.468
1.241
56
C5H4N), 123.5 (C, C5H4N), 129.2 (Cmeta
130.4 (Cpara
4 117/119Sn_13C, 20 Hz), 136.2 (Cortho
49 Hz), 136.8 (Cipso
1 117/119Sn_13C, 460 Hz), 137.5 (C5H4N). 119Sn
,
J
3 117/119Sn_13C, 61 Hz),
,
J
, J
2 117/119Sn_13C,
,
J
b (°)
V (Å3)
NMR (ppm): À33.3. Mass spectra data, tin-bearing fragment: m/e
351 [(C6H5)3Sn]+ (calcd 351), 309 [(C6H5)2SnCl]+ (calcd 309), 197
[(C6H5)Sn]+ (calcd 197), 155 [(SnCl)]+ (calcd 155), 120 [Sn]+ (calcd
120).
Z
qcalcd (g cmÀ3
)
l
(Mo K , mmÀ1
)
a
2hmax (°)
# ref. meas., unique
# of parameters
Rint
12445, 5375
266
0.0316
2.3. Crystal structure determination
R1, wR2 [I > 2
R1, wR2 (all data)
GooF
r
(I)]
0.0314, 0.0648
0.0261, 0.0625
1.057
The X-ray diffraction measurement was made on a STOE IPDS-II
diffractometer with graphite monochromated Mo K radiation. A
a
crystal of title compound with a dimension of 0.50 Â 0.40 Â
0.35 mm, was mounted on a glass fiber and used for data collec-
temperature in CDCl3 on a Bruker AVANCE 300-MHz operating at
300.3, 75.4 MHz and 111.9 MHz, respectively. The NMR spectra
are referenced to Me4Si (1H and 13C) or Me4Sn (119Sn) as external
standards. The mass spectroscopy was performed on a Varian
MAT 44 instrument (electron impact, 20 eV). The calculated isoto-
pic distribution for each ion was in agreement with experimental
values.
Table 2
Selected bonds length (Å) and angles (°) for title compound.
Bond lengths
Sn1–C1
Sn1–C7
Sn1–C13
Sn1–Cl1
2.122 (2)
2.124 (2)
2.124 (2)
2.4526 (7)
Sn1–O1
O1–H1
C19–O1
C25–N1
2.6263 (17)
0.79 (3)
1.428 (3)
1.341 (3)
Bond angles
C1–Sn1–C7
C1–Sn1–C13
C7–Sn1–C13
C1–Sn1–Cl1
C7–Sn1–Cl1
2.2. Synthesis and characterization
118.10 (8)
114.04 (8)
123.25 (8)
97.38 (6)
95.27 (6)
O1–Sn1–Cl1
C13–Sn1–Cl1
C25–N1–C21
C19–O1–H1
176.01(4)
98.88 (6)
117.8 (2)
106 (2)
The triphenyltin(IV) chloride (0.385 g, 1 mmol) was treated with
pyridine-2-ethanol (0.123 g, 1 mmol) in chloroform (10 ml) and was
refluxed for 2 h. Slow evaporation of the resulting solution furnished
Fig. 1. Molecular structure of [Ph3SnCl(HOC7H9N)] compound with ellipsoids at 30% probability. Hydrogen atoms are omitted for clarity.

46
A.R. Salimi et al. / Journal of Molecular Structure 937 (2009) 44–49
Fig. 2. Representation of trigonal bipyramidal geometry around tin (IV) atom.
tion. Cell constants and an orientation matrix for the data collec-
tion were obtained by least-squares refinement of diffraction data
from 5563 unique reflections (Table 1). Data were collected at a
temperature of 20 °C to a maximum 2h value of 53.6 and in a series
of x scans in 1° oscillations and integrated using the Stoe X-AREA
software package [12]. The numerical absorption coefficient, l, for
Mo K radiation is 0.918 mmÀ1. A numerical absorption correction
a
was applied using X-RED [13] and X-SHAPE software’s [14]. The
Fig. 3. Representation of symmetrical intermolecular hydrogen bonding between two monomeric complexes.

A.R. Salimi et al. / Journal of Molecular Structure 937 (2009) 44–49
47
data was corrected for Lorentz and Polarizing effects. The struc-
tures were solved by direct and subsequent difference Fourier
map and then refined on F2 by a full-matrix least-squares proce-
dure using anisotropic displacement parameters methods [15].
Subsequent refinement then converged with R factors and param-
eters errors significantly better than for all attempts to model the
solvent disorder. Atomic factors are from International Tables for
X-ray Crystallography [16]. All refinements were performed using
the X-STEP32 crystallographic software package [17].
nyl rings, respectively. Although, these values are significantly dif-
ferent from ideal value of 90° in tbp geometry, they are far from
that of in the tetrahedral Ph3SnCl (106.40°) [24]. It is of interest
to note that the pyridine-2-ethanol with two coordination sites
of N-pyridine and O-alcohol coordinated to the central tin atom
using hydroxyl group. Since the nitrogen atom of pyridine ring is
more basic than oxygen atom, it was expected nitrogen atom coor-
dinated to tin rather than oxygen, however, it seems due to the ste-
ric factor coordination of N-pyridine inhibited and instead the
2.4. Computational approach
All theoretical calculations were performed with the Gaussian
98 program package [18]. Full geometry optimizations of all inves-
tigated molecular structures were computed by density functional
theory (DFT) using the hybrid density functional B3LYP [19]. The
LanL2DZ basis set with quasi-relativistic effective core potentials
(LanL2) was used to represent the atomic cores and double-zeta
quality (DZ) to describe the valence electrons of tin atom. The stan-
dard basis set 6-31G (d, p) was used that use to describe the elec-
trons of carbon, nitrogen oxygen, and hydrogen atoms.
3. Results and discussion
3.1. General characterization
For the determination of structural feature of complex in solu-
tion, its 1H, 13C, and 119Sn has been recorded in CDCl3. The 1H
NMR spectrum of complex showed expected aliphatic and aro-
matic peaks with right multiplicities. Although, the 13C NMR spec-
trum of the title compound almost was identical with the 13C NMR
spectrum of triphenyltin(IV) chloride [20], the 119Sn NMR chemical
of it shifted 40 ppm to up field and indicate that the coordination
geometry in solution is somewhat different than triphenyltin(IV)
chloride [20]. The J
1 117/119Sn–13C value, 460 Hz, suggest that the
tin atom is pentacoordinated in solution [21,22]. The average
C–Sn–C angle in solution is estimated to be about 117.10° from
the magnitude of J
1 117/119Sn–13C [21]. The estimated value is in
good agreement with the C–Sn–C angles found in solid-state
(114.04–123.25°, average 118.46°), which indicates that the so-
lid-state structure and hydrogen bonding maintained in solution.
Fig. 4. Representation of crystal packing of titled compound along a-axis. Hydrogen
atoms are omitted for clarity.
3.2. Crystal structure description
Table 3
The adopted numbering scheme of the non-hydrogen atoms
along with the thermal vibrational ellipsoids is shown in an ORTEP
drawing of [Ph3SnCl(HOC7H9N)] complex (Fig. 1). Selected bond
distances and angles are listed in Table 2. In the titled compound,
Sn exhibit a slightly distorted trigonal–bipyramidal geometry
Geometrical parameters of calculated structures at the B3LYP level with experimental
data from X-ray analysis (distances in Å, angles in °).
Complex
C1.calc
Ligand
L1.calc
Exp.
C2.calc
L2.calc
Sn–O (hydroxyl group)
Sn–C (phenyl group)
Sn–Cl
2.479
2.140
2.507
2.620
2.132
2.496
2.626
2.123
2.453
(hereafter tbp), with trigonality index
where b is the greatest basal angle and
tude; = 0 and 1 for perfect square-pyramidal and trigonal–bipyra-
s
= 0.88 (
s
= (b À
a)/60,
a
is the second in magni-
s
C–C (phenyl group)
C–O (hydroxyl group)
C–N (pyridine ring)
O–H
1.400
1.434
1.343
0.995
1.400
1.429
1.346
0.995
1.379
1.428
1.342
0.793
midal geometries, respectively) [23] (Fig. 2).
1.412
1.343
0.975
1.407
1.342
0.984
Our findings confirm that the three carbon atoms of phenyl
rings are in equatorial position, while the chlorine and hydroxyl
group of alcohol occupy the apical positions with different bond
distances [Sn–Cl: 2.453 (1) Å and Sn–O: 2.626 (2) Å]. Furthermore,
the Cl–Sn–O bond angle of 176.01 (4)°, which is close to ideal value
of 180° in the axial position of tbp geometry, can be a clear evi-
dence for the interaction of hydroxyl group of pryridin-2-ethanol
moiety as a ligand with the central tin atom. In addition, the pla-
narity of carbon atoms of phenyl rings with tin atom is resulted
as a summation of C–Sn–C angles in the equatorial plane to
355.40°. Moreover, the C–Sn–Cl bond angles of title compound
are 97.38°, 95.27° and 98.88° for the C1, C7 and C13 atoms of phe-
O–H. . .N (intermolecular)
O. . .N
H. . .N
O–H. . .N
2.821
1.837
169.58
2.851
1.873
172.89
2.798
2.010
172.06
O–H. . .N (intramolecular)
O. . .N
H. . .N
O–H. . .N
2.656
1.771
146.28
2.820
2.013
138.79
C–Sn–C (summation)
Cl–Sn–O
355.88
176.06
355.92
177.98
355.40
176.01

48
A.R. Salimi et al. / Journal of Molecular Structure 937 (2009) 44–49
oxygen of the hydroxyl group with enhanced basicity due to
hydrogen bonding is coordinated to tin. This suggestion is in accor-
dance with the 119Sn NMR chemical shift that shows coordination
of pyridine-2-ethanol is maintained in solution. Alternatively,
coordination of oxygen of alcohol instead of nitrogen can be ex-
plained by steric demand of pyridine ring. The steric control over
the molecular structure of organotin compounds has been noticed
previously [25].
The crystal structure analysis reveals that the complex consists
of [Ph3SnCl(HOC7H9N)] discrete monomeric molecular units, which
are involved the hydrogen bonding between two units (Fig. 3). Two
hydrogen bonds (O1–H. . .N1, 2.010 Å; O1–H. . .N1, 172.06°) be-
tween alcohol hydroxyl group and pyridine ring of two monomers
give rise to a base pairing and forming dimmer complexes that ex-
hibit crystallographically imposed inversion symmetry. We pres-
ent a more detailed analysis of these hydrogen bonds and follow
this, dimmer complexes, in the computational section of this arti-
cle. Finally, the existence of dimeric units in tandem with electro-
static forces, generate an interesting zig-zag layered structure that
is viewed along a-axis in Fig. 4.
with consideration of relativistic effects for stannous have been
performed. Geometrical parameters of optimized structures are
listed in Table 3. The optimization of complex in form of a mono-
mer ended up with equilibrium structure that the conformation
of pyridine-2-ethanol ligand has changed in the calculated mono-
meric complex (C1.calc) (Fig. 5). The severe change in the confor-
mation of ligand is the rotation along with aliphatic bonds and
the change of dihedral angle of C20–C9–O1–H from À68.19° to
52.16° in initial and optimized structure of C1.calc, respectively,
which result in formation of strong intramolecular hydrogen bond-
ing between alcohol hydroxyl group and pyridine ring (O1–H. . .N1,
1.771 Å; O1–H. . .N1, 146.28°). In addition, the bond lengths of Sn–
O and Sn–Cl have changed to 2.479 and 2.507 Å, respectively.
Since, formation of complex is acid–base reaction between tin me-
tal atom and oxygen atom of hydroxyl group, one can found that
increases of the basicity of oxygen atom by hydrogen bonding
can decreases the Sn–O bond length.
DFT calculation of free ligand (L1.calc) shows that the change of
conformation of ligand occurs similarly. The intramolecular hydro-
gen bond, which forms with 2.013 Å and 138.79° distance and an-
gle respectively, indicate that pyridine-2-ethanol has hydrogen
bond in the complex stronger than free form.
3.3. Computational studies
The optimization of base paired dimmer complex (C2.calc) re-
veals that the change of conformation of ligand did not occur and
the structure of ligand retained without any rotation. In fact, the
existence of intermolecular hydrogen bonds between two mono-
mer that exist in the crystal structure can play a key role in the for-
To get insight into the hydrogen bonding in the title compound
and the pyridine-2-ethanol ligand, DFT calculations of monomer
complex [Ph3SnCl(HOC7H9N)] and the base paired dimmer com-
plex at the B3LYP/6-31G (d, p) level using effective core potential
Fig. 5. Calculated structures of monomer and dimmer complexes, C1.calc and C2.calc, and monomer and dimmer ligands L1.calc and L2.calc, respectively.

A.R. Salimi et al. / Journal of Molecular Structure 937 (2009) 44–49
49
mation of dimmer complex and stabilization of this structure in
the real system. In order to investigate the stabilization effect of
intermolecular instead of intramolecular hydrogen bond, calcula-
tion of base paired dimmer ligands (L2.calc) also has been carried
out. Similarly, in the dimmer complex, the structure of ligands re-
tained without any change in conformation. The O1–H. . .N1 dis-
tance; angle in C2.calc and L2.calc are 1.837 Å; 169.58° and
1.873 Å; 172.90° respectively. The bond lengths of Sn–O and Sn–
Cl and bond angle of Cl–Sn–O in C2.calc structure are 2.620 Å,
2.496 Å and 178.00°, respectively. Overall, the agreement between
geometrical parameters of calculated C2.calc and experimental
structures is very good.
The strength of hydrogen bonds calculated based on the ener-
gies differences of the paired dimmer complexes and ligands,
C2.calc and L2.calc, with the requisite monomer complex and li-
gand, respectively. The cleavage of the dimeric complex, which
having same hydrogen bond pattern as in L2.calc, to monomeric
units costs 83.51 kJ/mol (corrected for the basis set superposition
error, BSSE). This exhibits a moderate strength hydrogen bond [1]
for the C2.calc with energy of 41.76 kJ/mol. The analogous hydro-
gen bonds in L2.calc proved to be slightly stronger (41.84 kJ/mol,
BSSE corrected) than dimmer complex (C2.calc). Comparison of di-
meric complex (C2.calc), which it is consistent with the crystal
structure, with the monomeric complex of C1.calc that contains
intramolecular hydrogen bonding shows that the half energy of
dimmer is greater than monomer complex (8.63 kJ/mol). These re-
sults probably can explain reason for chose of dimeric structure by
complex.
charge from The Director, CCDC, 12 Union Road, Cambridge CB2
1EZ, UK (Fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk
or www: http://www.ccdc.cam.ac.uk).
Acknowledgments
We thank Ferdowsi University of Mashhad and Shahid Behehsti
University for supporting this work.
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In this study, a new adduct complex of triphenyltin(IV) chloride
and pyridine-2-ethanol has been prepared and characterized by
spectroscopic methods. DFT calculations of monomer complex
[Ph3SnCl(HOC7H9N)], dimmer complex, monomer free pyridine-
2-ethanol ligand, and dimeric form of ligands at the B3LYP/6-31G
(d, p) level have been carried out. Based on the theoretical results
we can conclude that intermolecular hydrogen bonding in the
crystal structure can play important role in the stabilization of title
compound as a dimeric complex. Theoretical results are in accor-
dance with the experimental data to good extent.
Supplementary material
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metallics 22 (2003) 4599.
Crystallographic data for the structural analysis have been
deposited with the Cambridge Crystallographic Data Centre, CCDC
No. 739025. Copy of this information may be obtained free of