Et4N[NO3(SnClPh3)2(SnPh 3NO3)]: A trinuclear organostannate complex and related derivatives

Article abstract of DOI:10.1515/mgmc-2013-0009

Four new di- and triorganonitrato stannate complexes and related derivatives have been synthesized and characterized by infrared and Moessbauer spectroscopy. The structure of Et₄N[NO ₃(SnClPh₃)₂(SnPh₃NO₃)](1) has been determined by single-crystal X-ray diffraction analysis. In the trinuclear organostannate complex, each Sn IV atom is five-coordinated and adopts a trigonal-bipyramidal trans -OXSnC₃(X = O or Cl) geometry. The overall coordination environment of the Sn^IV atoms is trans-octahedral for 2 and 3 or cis-trigonal-bipyramidal for 4. In the related derivatives, the NO₃^- anions behave as monodentate ligands.

Full text of DOI:10.1515/mgmc-2013-0009

ꢁ
ꢁꢁꢂ
DOI 10.1515/mgmc-2013-0009ꢀ
ꢀMain Group Met. Chem. 2013; 36(3-4): 83–88
Tidiane Diop*, Libasse Diop, François Michaud and José Domingos Ardisson
E t N[NO (SnClPh ) (SnPh NO )]: a trinuclear
4
3
3 2
3
3
organostannate complex and related derivatives
Abstract: Four new di- and triorganonitrato stannate com- et al., 2004; Basu et al., 2005; Hadjikakou and Hadjiliadis,
plexes and related derivatives have been synthesized and 2009). Reports on structure determinations or spectroscopic
characterized by infrared and Mössbauer spectroscopy. characterizations of triphenyltin(IV) derivatives with mono-
n-
The structure of Et N[NO (SnClPh ) (SnPh NO )] (1) has and polybasic oxyanions (XOm ; X=Cr, Se, S, As; m=3, 4; n=1,
4
3
3
2
3
3
been determined by single-crystal X-ray diffraction analy- 2, 3) show that the oxyanions behave mainly as polydentate
IV
sis. In the trinuclear organostannate complex, each Sn
ligands involving a one-dimensional polymeric, bi- or tridi-
atom is five-coordinated and adopts a trigonal-bipyramidal mensional network structure (Molloy et al., 1989; Diop et al.,
trans-OXSnC (X=O or Cl) geometry. The overall coordina- 2002; Diassé-Sarr et al., 2004; Fall et al., 2010; Boye et al.,
3
IV
tion environment of the Sn atoms is trans-octahedral for 2 2012). Some nitrato derivatives (Jurkschat et al., 2003a;
and 3 or cis-trigonal-bipyramidal for 4. In the related deri- García-Cuesta et al., 2004; Seward et al., 2007; Anjaneyulu
-
vatives, the NO anions behave as monodentate ligands.
et al., 2010; Hakimi et al., 2012) have also been reported. Our
groups have published some articles dealing with SnMe3-
3
Keywords: di- and triorganonitrato stannate; Mössbauer; and SnPh -containing derivatives with mono- and polybasic
3
2-
2-
-
2-
octahedral; trigonal-bipyramida; trinuclear.
oxyanions [SO , C O , PhP(H)O , HAsO ] (Sall et al., 1995;
4 2 4 2 4
Diallo et al., 2009; Gueye et al., 2011; Diop et al., 2013). In this
paper, we report on the reactions between tetraethylammo-
*
Corresponding author: Tidiane Diop, Laboratoire de Chimie
nium nitrate (Et NNO ) or dicyclohexylammonium nitrate
Minérale et Analytique, Département de Chimie, Faculté des
Sciences et Techniques, Université Cheikh Anta Diop (UCAD),
BP 5005, Dakar, Senegal, e-mail: tijchimia@yahoo.fr
4
3
(
Cy NH NO ) and mixing triphenyltin(IV) chloride (SnPh Cl)
2 2 3 3
or SnR Cl (R=Ph, Bu), which have yielded a trinuclear orga-
2
2
Libasse Diop: Laboratoire de Chimie Minérale et Analytique,
Département de Chimie, Faculté des Sciences et Techniques,
Université Cheikh Anta Diop, UCAD-sénégal, B.P 5005, Dakar, Senegal
François Michaud: Service Commun d’Analyse par Diffraction
Rayons X, Université de Bretagne Occidentale, 6 avenue Victor Le
Gorgeu, CS93837, 29238 Brest Cedex 3, France
nostannate complex and related derivatives. The structure
in the solid state of Et N[NO (SnClPh ) (SnPh NO )] has been
determined by single-crystal X-ray diffraction analysis. All
compounds have been characterized by Mössbauer and
infrared spectroscopy.
4
3
3
2
3
3
José Domingos Ardisson: Centro de Desenvolvimento da Tecnologia
Nuclear (CDTN), Servico de Nanotecnologia (SENAN), Laboratorio
de Fisica Aplicada, Av. Antonio Carlos 6.627, Campus da UFMG,
Pampulha, 31270-901 Belo Horizonte, MG, Brazil
Results and discussion
Molecular structure and spectroscopic charac-
terization of Et N[NO (SnClPh ) (SnPh NO )] (1)
Introduction
4
3
3 2
3
3
The various applications of organotin(IV) compounds The reaction of triphenyltin chloride (Ph SnCl) with
3
in many fields such as agriculture, medicine, antifou- Et NNO in the molar ratio 3:2 provided the trinuclear
4
3
ling paints, and wood preservatives are the main reasons organostannate complex Et N[NO (SnClPh ) (SnPh NO )]
4
3
3
2
3
3
several research groups are involved in the synthesis of new (1) as a colorless crystalline material that shows good sol-
organotin(IV) compounds (Růžička et al., 2002; Thoonen ubility in ethanol [Eq. (1)].
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4ꢀꢁꢁꢁꢂꢀT. Diop et al.: Et N[NO (SnClPh ) (SnPh NO )] trinuclear organostannate complex and derivatives
4
3
3
2
3
3
+
The trinuclear organostannate complex consists Between the Et N cations and the [NO (SnClPh ) (SnPh
4
3
3 2
-
-
of a discrete [NO (SnClPh ) (SnPh NO )] anion and a NO )] anion, the interactions are mainly of electrostatic
3
3
2
3
3
3
3
+
tetraethylammonium cation Et N (Figure 1). The [NO (Sn nature. The infrared (IR) spectrum of the complex in the
4
3
-
-1
ClPh ) (SnPh NO )] anion consists of two crystallographic 4000–400 cm region shows the presence of bands due to
3
2
3
3
-
1
-1
independent SnClPh moieties and one SnONO Ph moiety the nitrate ring vibrations at 1070 cm (s) and 1061 cm (s),
3
2
3
-1
-1
-1
that each show a distorted trigonal-bipyramidal environ- (ν NO ); 1334 cm (vs), 1362 cm (vs), and 1392 cm (vs) (ν
3
1
3
-
-
ment as a result of their simultaneous coordination to the NO ). The presence of two bands of ν NO reflects the two
3
1
3
central nitrate anion. The axial positions are occupied by types of nitrates.
O(1), O(4) (Sn1), Cl(1), O(2) (Sn2), and Cl(2), O(3) (Sn3),
whereas the equatorial positions are taken by the ipso
carbon atoms of the corresponding phenyl substituents.
Selected bond distances (Å)
The central nitrate anion is μ -bridging to three SnPh moi-
3
3
eties, and the second nitrate anion coordinates the Sn(1)
atom in a monodentate mode. A similar arrangement has
Sn(1)-O(4) 2.216(10); Sn(1)-O(1) 2.459(5); C(19)-Sn(2)
.128(5); C(31A)-Sn(2) 2.188(12); Sn(2)-O(2) 2.502(5); Sn(2)-
Cl(1) 2.512(4); C(37)-Sn(3) 2.134(5); C(43)-Sn(3) 2.125(4);
C(49A)-Sn(3) 2.045(11); Sn(3)-Cl(2) 2.453(3); N(1)-O(2)
2
been observed in the crystal structure of poly[μ -chlorido-
2
nonamethyl-μ -nitrato-tritin(IV)],ꢀꢀꢀ[(CH ) Sn] NO Cl,
3
3
3
3
3
(
Rehman et al., 2007) with a nitrate anion coordinated to
1
.242(7); N(1)-O(1) 1.248(7); N(1)-O(3) 1.251(7); N(2)-O(4)
.081(9); N(2)-O(5) 1.270(10); N(2)-O(6) 1.296(10); N(70)-
three Sn atoms. The Sn-O distances are in the accepted
range [Sn-O: 2.216(10) and 2.459(5) Å] and are shorter than
1
C(77)#1 1.492(15); N(70)-C(71)#1 1.500(14); N(70)-C(73)#1
.513(15).
+
-
the Sn-O distances in [Ph P] [(Ph ClSn) CH .NO ] [Sn-O:
4
2
2
2
3
1
2
.510(5) and 2.545(5) Å] (Jurkschat et al., 2003b), which are
very close to those observed in Et NNO .SnPh Cl [Sn-O:
4
3
2
2
2
.292(11) Å] (Diop et al., 2011). The sum of the O-N(1)-O
-
angles subtended at NO3 μ3-bridging [119.7° (6), 121.0° Selected bond angles (°)
(
6), and 119.3° (6)] is 360°, reflecting its trigonal-planar
geometry. The C-N(70)-C angles of the cation are close to C(7B)-Sn(1)-C(1A) 119.8(6); C(1B)-Sn(1)-C(7A) 123.9(6);
3
1
09°, in agreement with the expected sp hybridization. C(13)-Sn(1)-C(7A) 121.7(5); C(1A)-Sn(1)-C(7A) 116.5(6);
CI2
C49
Sn3
C37
C43
C19
O2
O3
N1
O1
Sn2
C31
C72
C13
CI1
C7
Sn1
C25
C71
C77
C76
O4
N2
N70
C73
C74
C1
C75
O6
C78
O5
Figure 1ꢀMolecular structure of Et N[NO (SnClPh ) (SnPh NO )] (1) showing the labeling scheme (the hydrogen atoms have been omitted for
4
3
3
2
3
3
clarity). Symmetry codes: (′) x, y, z (″) -x, -y, -z; displacement ellipsoids are drawn at the 50% probability level.
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T. Diop et al.: Et N[NO (SnClPh ) (SnPh NO )] trinuclear organostannate complex and derivativesꢀꢂꢁꢁꢁꢀ85
4
3
3
2
3
3
C(7B)-Sn(1)-O(4) 96.8(5); O(4)-Sn(1)-O(1) 171.5(3);
C(25A)-Sn(2)-C(31B) 117.1(8); C(25A)-Sn(2)-C(19) 116.8(5);
C(31B)-Sn(2)-C(19) 124.2(5); C(25A)-Sn(2)-C(31A) 123.2(7);
(
49A)-Sn(3)-C(43) 122.9(5); O(2)-N(1)-O(1) 119.7(6); O(2)-
N(1)-O(3) 121.0(6); O(1)-N(1)-O(3) 119.3(6); N(1)-O(1)-Sn(1)
25.4(4); N(1)-O(2)-Sn(2) 122.0(4); O(4)-N(2)-O(5) 125.3(11);
1
O(4)-N(2)-O(6) 122.8(10); O(5)-N(2)-O(6) 111.8(10); N(2)-
O(4)-Sn(1) 117.6(8); C(77)-N(70)-C(71) 110.1(12); C(77)-
N(70)-C(73) 113.0(12); C(71)-N(70)-C(73) 112.9(11); C(77)-
N(70)-C(75) 109.1(12).
Scheme 1ꢀSuggested structure for (Cy NH ) Cl SnBu (NO ) .
2
2
4
2
2
3 4
A and B refer to the disorder of the molecular struc-
ture at the temperature measured.
normal range for a diorganotin(IV) derivative (Davies and
Smith, 1982). The value of the quadrupole splitting (3.78
Spectroscopic characterization
of (Cy NH ) Cl SnBu (NO ) (2)
mm/s) is consistent with a trans hexacoordinated SnBu2
2
2 4
2
2
3 4
moiety (Scheme 1) according to Bancroft and Platt (1972).
2
-
Methanolic solutions containing Cy NH NO and SnBu Cl These [SnBu (NO ) ] , including the Cl atom, anions are
2
2
3
2
2
2
3 4
…
were mixed and stirred at room temperature for more than then connected by the cation through NH O hydrogen
h. The solution was allowed to evaporate to give powder bonds responsible for the strong IR absorptions at 3340
1
-1
of the title compound [Eq. (2)].
and 3215 cm .
In comparison with the data reported for other nitrato Spectroscopic characterization
adducts or derivatives (Addison et al., 1967; Nakamoto,
of (Cy NH ) SnPh Cl (NO ) (3)
2
2 2
2
2
3 2
1
997), we suggest the following IR band assignments to be
-
1
made for the compound. The bands located at 1061 cm
1 3 3 3
assigned to the vibrations of the NO groups.
The title compound, (Cy NH ) SnPh Cl (NO ) (3), was pre-
2
2
2
2
2
3 2
-1
-1
(
s,ꢀν NO ), 1335 cm (vs), and 1370 cm (vs), (ν NO ) are pared by the condensation reaction of diphenyltin(IV)
dichloride with Cy NH NO in a 1:2 molar ratio [Eq. (3)].
2 2 3
3
The absence of ν SnBu in the IR spectrum indicates
In the IR spectrum, the bands located at 1060 (s,
s
2
-1
the n-Bu substituents to be trans. The Mössbauer spectrum ν NO ), 1334, and 1375 (vs,ꢀν NO ) cm are assigned to the
1
3
3
3
of compound 2 shows a slightly asymmetric quadrupole stretching vibrations of the NO groups. The value of the
3
-1
split doublet with an isomer shift value (1.20 mm ) in the quadrupole splitting of (3) (QS=3.57 mm/s) is consistent
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6ꢀꢁꢁꢁꢂꢀT. Diop et al.: Et N[NO (SnClPh ) (SnPh NO )] trinuclear organostannate complex and derivatives
4
3
3
2
3
3
dicyclohexylammonium cation connects adjacent anionic
-
…
[
SnPh (NO ) ] layers through N-H O hydrogen bonding
2 3 3
into a three-dimensional network structure. The Cl atom
can be involving in the hydrogen bonds network of supra-
molecular architecture.
Experimental
Scheme 2ꢀSuggested structure for (Cy NH ) SnPh Cl (NO ) .
2
2
2
2
2
3 2
Materials and spectroscopic methods
with the presence of a trans hexacoordinated SnPh group
2
SnPh Cl , SnBu Cl , SnPh Cl, AgNO , Et NCl, HNO , and Cy NH were
2
2
2
2
3
3
4
3
2
according to Bancroft and Platt (1972). The suggested
purchased from Aldrich or Merck Chemical Company and used with-
out further purification.
structure for (3) consists of a trans-octahedral geometry
IV
around the Sn atom (Scheme 2). The dicyclohexylammo-
The infrared spectra were recorded at the laboratory of control
medicine (Dakar) by means of a Bruker FT-IR type spectrometer;
2-
nium cation connects adjacent anionic [SnPh (NO ) Cl ]
2
3
2
2
…
layers through N-H O hydrogen bonding into a three- the samples were prepared as KBr pellets. Elemental analyses were
performed at the University of Bath (UK) using an Exeter Analyti-
dimensional network structure.
-1
cal CE440 analyzer. Infrared data are given in cm (abbreviations:
1
19
vs, very strong; s, strong; m, medium; w, weak). Sn Mössbauer
spectra were obtained from a constant-acceleration spectrometer
Spectroscopic characterization
of (Cy NH ) ClSnPh (NO ) (4)
moving a CaSnO source at room temperature. The samples were
3
2
2 2
2
3 3
analyzed at liquid N temperature, and the isomer shif values are
2
given with respect to that source. All the Mössbauer spectra were
computer-fitted assuming Lorentzian lineshapes. Mössbauer para-
meters are given in mm/s (abbreviations: QS, quadrupole splitting;
IS, isomer shif ).
(
Cy NH ) ClSnPh (NO ) (4) has been prepared by allowing
2
2
2
2
3 3
Cy NH NO to react with diphenyltin dichloride, Ph SnCl ,
2
2
3
2
2
in methanol in the molar ratio 1:3 [Eq. (4)] (Scheme 3).
The value of the quadrupole splitting (QS=3.07 Synthesis of ligands
mm/s) is consistent with a cis-trigonal-bipyramidal coor-
Et NNO (L ) was obtained on mixing AgNO (0.50 g, 2.95 mmol) with
4
3
1
3
dinated SnPh residue according to Bancroft and Platt
2
tetraethylammonium chloride (Et NCl) (0.82 g, 2.95 mmol) both in
4
IV
(
1972). The overall coordination environment of the Sn
atom is trigonal-bipyramidal defined by two phenyl C
water and filtering off the AgCl precipitate (Sall et al., 1995).
Cy NH NO (L ) was obtained as a precipitate on mixing an aque-
2
2
3
2
atoms in cis positions and three nitrate O atoms. The ous solution of Cy NH with NO H in 1:1 ratio. Analytical data: % found
2
3
(
(
% calc. for ligand): % C, 58.76 (58.99); % H, 9.56 (9.90); % N, 11.00
11.47).
Synthesis of Et N[NO (SnClPh )
4
3
3 2
(
SnPh NO )](1)
3
3
Regular crystals of Et N[NO (SnClPh ) (SnPh NO )] suitable for
4
3
3
2
3
3
X-ray work were obtained af er a slow solvent evaporation of the
solution obtained on SnPh Cl (0.23 g, 0.6 mmol) with Et NNO
Scheme 3ꢀSuggested structure for (Cy NH ) ClSnPh (NO ) .
2
2
2
2
3
3
3
4
3
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T. Diop et al.: Et N[NO (SnClPh ) (SnPh NO )] trinuclear organostannate complex and derivativesꢀꢂꢁꢁꢁꢀ87
4
3
3
2
3
3
3
(
0.12 g, 0.40 mmol) in methanol in 3:2 ratio [melting point (mp), hole (eÅ ): 1.763, -0.672. The structure itself is highly disordered ow-
260°C; yield, 82%]. ing to the temperature measurement [298(2) K]. The crystallographic
+
Analyticaldata:[%found(%calc.)forC H Cl N O Sn ,1375.14g]: data for CCDC 859692 contain the supplementary crystallographic
6
2
65
2
3
6
3
-1
%
3
C: 54.32 (54.15); % H: 4.34 (4.76); % N: 2.95 (3.06). IR (cm , KBr):
078 m (ν CH), 1070 s, and 1061 s (ν NO ); 1334 vs, 1362 vs, and 1392
data for this paper.
1 3
vs (ν NO ).
3
3
Synthesis of (Cy NH ) Cl SnBu (NO ) (2)
2
2 4
2
2
3 4
X-ray crystallographic data of
(Cy NH ) Cl SnBu (NO ) (2) has been obtained by reacting (L )
2 2 4 2 2 3 4 2
0.20 g, 0.80 mmol) with dibutyltin(IV) dichloride (SnBu Cl ) (0.06 g,
(
Et N[NO (SnClPh ) (SnPh NO )] (1)
2 2
4
3
3 2
3
3
0
.20 mmol) in methanol. Af er a slow solvent evaporation a white
A crystal of approximate dimensions 0.13 mm×0.08 mm×0.07 mm
was used for data collection. Data were collected at 298(2) K using
Mo-kα radiation (λ=0.71073 Å).
powder was collected in the solvent (81%, mp 200°C).
Analytical data: [% found (% calc.) for C56H114Cl O12Sn, 1280.7 g]:
2
-1
% C: 52.56 (52.50); % H: 8.92 (8.97); % N: 8.70 (8.75). IR (cm , KBr):
340 s and 3215 s (ν NH ), 3160 m (ν NH), 3078 m (ν CH), 1061 s
3
2
(
ν NO ); 1335 vs and 1370 vs (ν NO ), 669w (ν SnBu ). Mössbauer
1
3
3
3
a
s
2
data (mm/s): IS=1.20, QS=3.78.
2
Refinement of F against ALL reflections
The weighted R factor wR and goodness of fit S are based on F2,
and conventional R factors R are based on F, with F set to zero for
Synthesis of (Cy NH ) SnPh Cl (NO ) (3)
2
2 2
2
2
3 2
2
2
2
negative F . The threshold expression of F >2σ(F ) is used only for
calculating R factors (gt), etc. and is not relevant to the choice of re-
An ethanolic solution containing 0.10 g (0.4 mmol) of L and 0.07 g
2
(
0.2 mmol) of diphenyltin(IV) dichloride (SnPh Cl ) was stirred at
2
2 2
flections for refinement. R factors based on F are statistically about
room temperature for more than 1 h. Af er a slow solvent evaporation
of the solution a white powder was obtained (78%, mp 160°C).
Analytical data: [% found (% calc.) for C H Cl N O Sn,
twice as large as those based on F, and R factors based on all data
will be even larger.
3
6
58
2
4
6
8
(
32.28 g]: % C: 52.00 (51.94); % H: 7.00 (7.02); % N: 6.70 (6.73). IR
-1
cm , KBr): 3321 and 3000 m (ν NH ), 3160 m (ν NH), 3072 m (ν CH),
2
Data collection
1060 s (ν NO ); 1334 vs, and 1375 vs (ν NO ). Mössbauer data (mm/s):
IS=1.25, QS=3.57.
1
3
3
3
CrysAlis CCD, Oxford Diffraction (2009); cell refinement: CrysAlis
RED, Oxford Diffraction (2009); data reduction: CrysAlis RED, Oxford
Diffraction; program used to solve structure: SHELXS97 (Sheldrick,
Synthesis of (Cy NH ) ClSnPh (NO ) (4)
2
008); program used to refine structure: SHELX97 (Sheldrick, 2008);
2
2 2
2
3 3
molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); sof ware
used to prepare material for publication: enCIFer (Allen et al., 2004),
PlATON (Spek, 1990, 1998), WinGX (Farrugia, 1999).
(
Cy NH ) ClSnPh (NO ) (4) has been obtained by reacting 0.10 g
2 2 2 2 3 3
0.4 mmol) of L with 0.05 g (0.13 mmol) of diphenyltin(IV) dichloride
(
2
(
SnPh Cl ) in methanol. Af er a slow solvent evaporation a white pow-
2 2
der was collected in the solvent (79%, mp 173°C).
Analytical data: [% found (% calc.) for C H ClN O Sn,
3
6
58
5
9
8
59.04 g]: % C: 50.23 (50.33); % H: 6.80 (6.81); % N: 8.40 (8.15). IR
Crystal data and structure refinement
-
1
(
cm , KBr): 3340 and 3215 m (ν NH ), 3160 m (ν NH), 3078 m (ν CH),
2
1
061 s (ν NO ); 1340 vs, and 1370 vs (ν NO ). Mössbauer data (mm/s):
1 3 3 3
Empirical formula: C H Cl N O Sn ; formula weight=1375.14; crystal
62
65
2
3
6
3
IS=1.30, QS=3.07.
system: triclinic; space group: P-1; a=14.0465(12) Å; b=15.0816(10)
o
Å; c=16.0431(13) Å; α (°) = 85.611(6), β ( ) =85.599(7), γ(°) =63.381(7);
Acknowledgements: We thank Professor K. C. Molloy
University of Bath, UK) for performing the elemental
3
3
-1
V (Å ) =3026.0(4); Z=2; ρ (mg/m ) =1.509; μ(Mo-k ) (mm ) =1.368;
calc
α
(
F(000): 1380; reflections collected: 23,179; independent reflections
[
R(int)]: 12,346 [0.062]; reflections observed (>2σ): 6014; absorption analyses, and Djibril Fall (Cheikh Anta Diop University,
correction: semiempirical from equivalents; maximum, minimum Dakar , Senegal) for recording the infrared spectrum.
transmission: 0.9103, 0.8422. Refinement method, full-matrix least
2
squares on F ; goodness of fit, 0.825; final R indices [I>2σ(I)]: 0.0659,
Received February 20, 2013; accepted February 23, 2013; previously
published online June 18, 2013
0
.1588; R indices (all data): 0.1502, 0.1832; largest difference peak and
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8ꢀꢁꢁꢁꢂꢀT. Diop et al.: Et N[NO (SnClPh ) (SnPh NO )] trinuclear organostannate complex and derivatives
4
3
3
2
3
3
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