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In the crystalline state, the low-melting title compound [common name: diphenyl­tin(IV) dibromide], [SnBr2(C6H5)2], consists of distorted tetra­hedral mol­ecules with compressed halide and enlarged carbon opening angles of 102.741 (9) and 123.53 (8)°, respectively, and Sn—C and Sn—Br bond lengths of 2.109 (2)/2.113 (2) and 2.4710 (3)/2.4947 (3) Å, respectively. Inter­molecular Sn...Br inter­actions, typical for diorganotin(IV) dihalides, R2SnHal2 (with Hal = Cl, Br, I), and sterically less demanding organic groups lead to the formation of a hitherto unknown association pattern consisting of centrosymmetric dimers with an anti­parallel orientation of the dipole moments and two weak inter­molecular Sn...Br distances of 3.8482 (3) Å between one of the two Br atoms and its neighbouring Sn atom, and vice versa. The second Br atom is not involved in inter­molecular inter­actions and lies somewhat outside the association plane that, therefore, is not coplanar [inter­planar angle = 1.750 (2)°] with the tin–halide plane. The new structure motif of inter­molecular tin–halide inter­action can be classified as 2ai, which indicates the number of mol­ecules (i.e. `2') composing the oligomer, the anti­parallel orientation (i.e. `a') of their dipole moments and the centre of symmetry (i.e. `i') giving rise to the association pattern.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112012504/fg3245sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112012504/fg3245Isup2.hkl
Contains datablock I

CCDC reference: 879433

Comment top

Diorganotin(IV) dihalides, denoted R2SnHal2 (Hal = Cl, Br, I; R = nonfunctionalized organic groups), are easy to prepare and versatile starting materials for the preparation of many other diorganotin derivatives, such as alkoxides (Bradley et al., 1978), hydrides (Ingham et al., 1960), tetraorganodistannoxanes (Jurkschat, 2008), carboxylates (Mehrotra & Bohra, 1980) or different coordination monomers and polymers that are not only important in basic research for the formation of, for example, supramolecular assemblies (Dakternieks & Duthie, 2003; Haiduc, 2007) or metal–organic frameworks (MOFs) (Shankar et al., 2011), but are also used in industry as PVC stabilizers (Arkis, 2008) or catalysts (Evans & Karpel, 1985).

In the gas phase, they consist of monomeric molecules of point-group symmetry C2v with a considerable dipole moment (Lorberth & Nöth, 1965) in the direction of the twofold axis of symmetry. For dimethyltin(IV) dichloride, Me2SnCl2 (Fujii & Kimura, 1971), and di-tert-butyltin(IV) dichloride, tBu2SnCl2 (Belyakov et al., 1988), the four main structural parameters (Sn—Hal, Sn—C, Hal—Sn—Hal and C—Sn—C) were determined by electron diffraction experiments. Deviations from a tetrahedral bond arrangement at the Sn atom mainly result from bond-angle distortions which are small in the case of Me2SnCl2 (Cl—Sn—Cl = 107.5±3.9°) but considerable for tBu2SnCl2 (C—Sn—C = 118.6±4.2° and Cl—Sn—Cl = 103.1±4.5°).

In different noncoordinating organic solvents, such as toluene or chloroform, they also represent monomeric molecules, whereas coordination compounds are formed in the case of solvent molecules with donor atoms like N [e.g. N-dimethylformamide (DMF) or dimethyl sulfoxide (DMSO)] as a result of Lewis base–Lewis acid adduct formation between the solvent molecule and the diorganotin(IV) dihalide unit.

In the solid state, diorganotin(IV) dichlorides, bromides and iodides with large voluminous organic residuals like tert-butyl [tBu2SnCl2; Dakternieks et al., 1994], 2-methyl-2-phenylpropyl [(MePhPr)PhSnBr2; Bomfim et al., 2003] or mesityl [Mes2SnBr2; Chandrasekhar & Thirumoorthi, 2010] are monomeric also, with large carbon and small halide opening angles, viz. 133.1 (2) and 101.86 (5)° in tBu2SnCl2, 127.0 (1) and 102.18 (1)° in (MePhPr)PhSnBr2, and 118.7 (2) and 100.51 (2)° in Mes2SnBr2.

The corresponding diorganotin(IV) dihalides with organic ligands of small steric requirements, however, show a strong tendency for intermolecular association as result of intermolecular tin (Lewis acid) halide (Lewis base) interactions for which such terms like `secondary bonding' (Alcock & Sawyer, 1977), `supramolecular architecture' (Buntine et al., 2003) or `soft–soft interactions' (Haiduc, 2007) were used. Usually, these additional (sec) bonds are considerably longer than normal (cov) ones, but shorter than van der Waals (vdW) contacts: d(Sn—Hal)cov d(Sn···Hal)sec d(Sn···Hal)vdW. Furthermore, they are accompanied by an increase of the coordination number at tin from four to five or six, resulting in a distorted trigonal–bipyramid or a distorted octahedron as the coordination polyhedron.

In the case of small organic ligands, predominantly infinite polymeric chains are formed which we propose to term einer-single chains following the terminology of silicates (Liebau, 1985) in order to delimit these structures from others. There are two main structure-type families in this area: one with an antiparallel (A) or nearly antiparallel ordering of the dipole moments of neighbouring molecules and the other where they are parallel (P) or nearly parallel to each other. The aristotypes of these structure-type families (Fig. 1) are represented by dimethyltin(IV) dichloride (Me2SnCl2; Reuter & Pawlak, 2001a) as type A and diethyltin(IV) diiodide (Et2SnI2; Alcock & Sawyer, 1977) as type P. The less symmetrical members of both structure-type families can be further classified according to the symmetry elements responsible for the chain propagation. Other structure types based on an infinite polymeric association pattern can be classified as einer-double chains or bands (β-Cy2SnCl2; Ganis et al., 1986), zweier-single chains (Ph2SnCl2; Greene & Bryan, 1971) or sheets (EtPhSnCl2; Casas et al., 2003).

On the other hand, finite oligomeric association patterns are rare. Applying the bond criteria defined above, there is only one example of a noncentrosymmetric dimer, viz. trans-Myr2SnCl2 (Myr = myrtanyl; Beckmann et al., 2008), with an antiparallel orientation of the dipole moments and one example of a centrosymmetric tetramer (MePhSnCl2; Amini et al., 1987), also with an antiparallel orientation of the dipole moments.

With the crystal structure of dibromodiphenylstannane, Ph2SnBr2, (I), we present the first example of a diorganotin(IV) dihalide exhibiting a centrosymmetric dimeric association pattern in the solid state.

(I) is a colourless low-melting solid (m.p. 309–311 K) that can be easily prepared (Chambers & Scherer, 1926) from commercially available tetraphenylstannane and bromine using carbon tetrachloride as solvent. Yields are usually moderate ( 35%) because of the formation of the side products bromotriphenylstannane and bromobenzene.

The asymmetric unit of (I) (Fig. 2) consists of one molecule of local point-group symmetry C1. Both phenyl groups are almost planar [maximum deviations from least-squares planes = ±0.002 (2) Å for the C11–C16 ring and ±0.003 (2) Å for the C21–C26 ring] and bond lengths within the phenyl groups covering the range 1.375 (4)–1.395 (3) Å, with a mean value of 1.385 (7) Å, are as expected (Allen et al., 1987). Distortions of the bond angles within the organic groups are small and in the range 119.1 (2)–120.9 (2)°, an ipso effect (Domenicano et al., 1983) is not recognizable, but the Sn atom lies significantly outside [0.038 (3) and -0.044 (3) Å] the least-squares planes through both phenyl groups. Both Sn—C bonds are very similar [mean value = 2.111 (3) Å] and comparable with other tin–phenyl bond lengths with tin in a predominantly tetrahedral environment, such as in triphenyltin(IV) bromide (Ph3SnBr; Preut & Huber, 1979), where a mean value of 2.114 (8) Å (T = 293 K) was found.

Both Sn—Br bond lengths are also very similar [Δ = 0.0237 Å and mean value = 2.483 (17) Å] but considerably ( 0.1 Å) shorter than the sum (2.59 Å) of the covalent radii (Cordero et al., 2008) of tin (1.39 Å) and bromine (1.20 Å). They fit very well into the range (2.44–2.54 Å) of Sn—Br bond lengths found in other [ten compounds with 14 individual values; Cambridge Structural Database (Allen, 2002)] diorganotin(IV) dibromides with nonfunctionalized hydrocarbon groups, even if the literature data cover all kinds of intermolecular association patterns and are derived from X-ray diffraction measurements at different temperatures. They are, however, longer than the corresponding bond lengths [mean value = 2.423 (4) Å, T = 249 K) in tin(IV) bromide (Reuter & Pawlak, 2001b). Because of the low symmetry of the molecule, the tin–halide plane is not exactly perpendicular to the tin–carbon plane, but the deviation of 0.14 (4)° is negligible.

The bromine and carbon opening angles (Table 1) of (I) are compressed and significantly enlarged, respectively. A detailed comparison with the corresponding values of other diorganotin(IV) dibromides, however, is difficult because other association patterns will give clearly different values. In addition, monomeric diorganotin(IV) dibromides show a similar broad spectrum of carbon and bromine opening angles as can be seen from the examples Mes2SnBr2 and MePhPr)PhSnBr2 above.

Looking for intermolecular Sn···Br interactions, we have taken into account all intermolecular Sn···Br distances shorter than the sum (4.00 Å) of the van der Waals radii (Mantina et al., 2009) of tin (2.17 Å) and bromine (1.83 Å). Indeed, there are only two intermolecular Sn···Br contacts of 3.8482 (3) Å fulfilling this criterion. These contacts exist between the Sn and Br atoms (Br2) of two molecules related to each other by a crystallographic (1/2,0,0; Wyckoff letter b) centre of symmetry (Fig. 3). The intermolecular bond angles within the four-membered centrosymmetric tin–bromine ring are Sn—Br···Sn = 101.92 (1)° and Br—Sn···Br = 78.08 (1)°.

For further discussion of the association pattern of oligomeric diorganotin(IV) dihalides, it seems helpful to determine the four-membered tin–halide ring as [an] aggregation plane. Because of the centre of symmetry, this reference plane is almost planar in the present case, in contrast to the nonplanar aggregation plane in trans-Myr2SnCl2. In relation to the aggregation plane, Br1 is 0.0742 (3) Å below it. As a consequence, the tin–halide plane is not coplanar with the reference plane, resulting in an interplanar angle of 1.750 (2)°. Furthermore, the dipole moments of both molecules which are exactly antiparallel to each other (inversion centre) will be situated somewhat outside the association plane. Taking the weak intermolecular interactions into account, the Sn atoms adopt a fivefold trigonal–bipyramidal coordination with the organic groups in equatorial and atoms Br1 and Br2i in axial positions [symmetry code: (i) -x+1, -y, -z]. This may be the reason why the Sn—Br distance to Br1 is somewhat longer than to Br2, although this atom interacts with the neighbouring Sn atom. The crystal packing (Fig. 4) reveals that the phenyl groups completing the dimers inhibit further intermolecular Sn···Br interactions.

In order to classify the association pattern of diorganotin(IV) dihalides more rationally, we propose to denote the new association pattern as 2ai, where `2' indicates the number of molecules comprising the oligomer, `a' represents the antiparallel orientation of the dipole moments of both molecules and the subscript `i' represents the symmetry element leading to the association pattern. In doing this, the noncentrosymmetric dimers of trans-Myr2SnCl2 (see above) can be classified as 2a1.

In addition, the new structure motif for the intermolecular Sn···Br interaction in Ph2SnBr2 shows some important relationships to other structure types in the field of diorganotin(IV) dihalides: for one thing, dimers with [an] antiparallel orientation of dipole moments are the shortest possible oligomeric sections within the structure family of Me2SnCl2, and for another thing, the structure type of Ph2SnCl2, which is characterized as zweier-single chain, is built up of two different centrosymmetric dimers of type 2ai with each Sn atom undergoing an additional interaction to the exocyclic chlorine atom of a neighbouring dimer, and vice versa. Applying our classification scheme, this structure type can be expressed by the term C2(2ai), with the letter C being an abbreviation for the chain structure motif and 2(2ai) as repeat unit.

Related literature top

For related literature, see: Alcock & Sawyer (1977); Allen (2002); Allen et al. (1987); Amini et al. (1987); Arkis (2008); Beckmann et al. (2008); Belyakov et al. (1988); Bomfim et al. (2003); Bradley et al. (1978); Buntine et al. (2003); Casas et al. (2003); Chambers & Scherer (1926); Chandrasekhar & Thirumoorthi (2010); Cordero et al. (2008); Dakternieks & Duthie (2003); Dakternieks et al. (1994); Domenicano et al. (1983); Evans & Karpel (1985); Fujii & Kimura (1971); Ganis et al. (1986); Greene & Bryan (1971); Haiduc (2007); Holeček et al. (1990); Ingham et al. (1960); Jurkschat (2008); Liebau (1985); Lorberth & Nöth (1965); Mantina et al. (2009); Mehrotra & Bohra (1980); Poller (1962); Preut & Huber (1979); Reuter & Pawlak (2001a, 2001b); Shankar et al. (2011).

Experimental top

A solution of tetraphenyltin (21.36 g, 50 mmo, Janssen Chimica) and bromine (15.98 g, 100 mmol, Fluka) in carbon tetrachloride (150 ml, Fluka) was heated for 3 h under reflux. After filtration, the solvent was removed under reduced pressure. The residue was purified by fractional dstillation of PhBr (300 K, 0.37 bar), PhSnBr3 (358–361 K, 0.17 bar) and Ph2SnBr2 (396–402 K, 0.16 bar). After cooling, colourless crystals of the title compound were obtained in a yield of 33.09%. Elemental data (Elementar vario MICRO Cube, calculated/found, %): C 33.31/32.91, H 2.33/2.26.

ATR–FT–IR (Bruker VERTEX 70, cm-1): 3068.0 [w, ν(CH)], 1576.2 [w, ν(CC)], 1479.0 [w, ν(CC)], 1430.6 [s, ν(CC)], 1331.8 [m, ν(CC) and δ(CH)ip], 1301.5 [w, δ(CH)ip], 1189.3 [w, δ(CH)ip], 1159.8 [w, δ(CH)ip], 1070.5 [m, δ(CH)ip], 1020.3 [w, δ(CH)ip], 995.3 [m, δ(ring)], 913.2 [m, δ(CH)oop], 724.5 [s s, δ(CH)oop], 688.0 [s s, δ(CH)oop]; assignments according to Poller (1962).

1H NMR (Bruker AVANCE DPX, 250 MHz, CDCl3): δ 7.34–7.51(m, 3H, meta,para); 7.55–7.62 (m, 2H, ortho).

{1H} 13C NMR (Bruker AVANCE DPX, 250 MHz, CDCl3): δ [nJ (Hz)] 128.1 [Cmeta, 3J(13C–119Sn/117Sn) = 84.2/80.6], 130.2 [Cpara, 4J(13C–119/117Sn) = 17.3], 133.4 [Cortho, 2J(13C–119Sn/117Sn) = 63.9/61.5], 135.8 [Cipso, 1J(13C–119Sn/117Sn) = 728.8/696.5]; for literature data, see Holeček et al. (1990).

A suitable single crystal was selected under a polarization microsope and mounted on a 50 µm MicroMesh MiTeGen Micromount using Fromblin Y perfluoropolyether (LVAC 16/6, Aldrich).

Refinement top

All H atoms were found in a difference Fourier synthesis, but were placed in geometrically idealized positions, with C—H = 0.95 Å, and constrained to ride on their parent atoms, with one common isotropic displacement parameter for each of the two phenyl groups.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Schematic representation of the tin–halide interactions (broken bonds) and the orientation of the dipole moments (red arrows of arbitrary units) in the crystal structures Me2SnCl2 and Et2SnI2. In both cases, the halide atoms of one molecule are individually labelled although they are symmetry related in the real structures. Organic groups have been omitted for clarity.
[Figure 2] Fig. 2. A view of the molecule of (I) in parallel projection, showing the atom-labelling scheme. Diplacement ellipsoids are drawn at the 50% probability level.
[Figure 3] Fig. 3. Capped sticks model (right side) of the centrosymmetric dimers resulting from intermoelcular Sn···Br interactions [3.8482 (3) Å, broken sticks] in the crystal structure of (I). A detailed view of the centrosymmetric dimers (left side) projected (above) on the association plane [Sn1—Br2—Sn1i—Br2i, grey; i = centre of inversion) and a view (below) showing the antiparallel orientation of the dipole moments (arrows of arbitrary units) and the out-of-plane positions of the exocyclic Br1 and Br1i atoms. The positions of the phenyl groups are indicated by shortened sticks. [Symmetry code: (i) -x+1, -y, -z.]
[Figure 4] Fig. 4. The crystal packing of (I), viewed down the b axis, showing the isolated centrosymmetric dimers formed by intermolecular Sn···Br interactions.
Dibromodiphenylstannane top
Crystal data top
[SnBr2(C6H5)2]F(000) = 808
Mr = 432.71Dx = 2.181 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8762 reflections
a = 8.9553 (5) Åθ = 2.4–28.0°
b = 8.7468 (5) ŵ = 7.97 mm1
c = 17.0671 (8) ÅT = 100 K
β = 99.713 (2)°Bloc, colourless
V = 1317.71 (12) Å30.23 × 0.17 × 0.13 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
3182 independent reflections
Radiation source: fine-focus sealed tube2856 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ϕ and ω scansθmax = 28.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1111
Tmin = 0.262, Tmax = 0.419k = 1111
46736 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.017Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.039H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0169P)2 + 0.9678P]
where P = (Fo2 + 2Fc2)/3
3182 reflections(Δ/σ)max = 0.002
138 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.48 e Å3
Crystal data top
[SnBr2(C6H5)2]V = 1317.71 (12) Å3
Mr = 432.71Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.9553 (5) ŵ = 7.97 mm1
b = 8.7468 (5) ÅT = 100 K
c = 17.0671 (8) Å0.23 × 0.17 × 0.13 mm
β = 99.713 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
3182 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2856 reflections with I > 2σ(I)
Tmin = 0.262, Tmax = 0.419Rint = 0.031
46736 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0170 restraints
wR(F2) = 0.039H-atom parameters constrained
S = 1.05Δρmax = 0.43 e Å3
3182 reflectionsΔρmin = 0.48 e Å3
138 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.671404 (15)0.195428 (14)0.073759 (8)0.02111 (4)
Br10.80819 (2)0.44485 (2)0.081248 (14)0.03092 (6)
Br20.54784 (3)0.18404 (3)0.066963 (13)0.03211 (6)
C110.8398 (2)0.0242 (2)0.09497 (12)0.0238 (4)
C120.8450 (2)0.0892 (2)0.03800 (14)0.0291 (5)
H120.77220.09070.00940.042 (3)*
C130.9573 (3)0.1993 (2)0.05120 (17)0.0382 (6)
H130.96170.27660.01250.042 (3)*
C141.0628 (3)0.1977 (2)0.12013 (18)0.0428 (6)
H141.13910.27410.12880.042 (3)*
C151.0580 (3)0.0858 (3)0.17647 (17)0.0410 (6)
H151.13100.08510.22380.042 (3)*
C160.9465 (2)0.0260 (2)0.16398 (14)0.0326 (5)
H160.94330.10360.20260.042 (3)*
C210.5000 (2)0.2236 (2)0.14348 (12)0.0222 (4)
C220.3820 (2)0.3262 (2)0.12122 (14)0.0303 (5)
H220.37840.38710.07480.044 (3)*
C230.2690 (3)0.3386 (3)0.16780 (16)0.0411 (6)
H230.18750.40810.15300.044 (3)*
C240.2748 (3)0.2500 (3)0.23569 (16)0.0419 (6)
H240.19780.25980.26740.044 (3)*
C250.3914 (3)0.1483 (3)0.25729 (14)0.0376 (5)
H250.39480.08750.30370.044 (3)*
C260.5034 (3)0.1346 (2)0.21136 (12)0.0291 (5)
H260.58370.06390.22620.044 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02097 (8)0.02129 (7)0.02126 (8)0.00134 (5)0.00415 (5)0.00069 (5)
Br10.03290 (12)0.02184 (10)0.04005 (13)0.00479 (8)0.01202 (10)0.00286 (8)
Br20.03074 (12)0.04248 (13)0.02239 (11)0.00606 (9)0.00238 (9)0.00078 (9)
C110.0210 (10)0.0203 (9)0.0311 (11)0.0042 (7)0.0075 (9)0.0014 (8)
C120.0289 (11)0.0241 (10)0.0368 (12)0.0064 (8)0.0128 (10)0.0023 (8)
C130.0385 (14)0.0197 (10)0.0633 (17)0.0053 (9)0.0284 (13)0.0022 (10)
C140.0256 (12)0.0242 (11)0.082 (2)0.0013 (8)0.0187 (13)0.0132 (11)
C150.0247 (12)0.0356 (12)0.0586 (16)0.0054 (9)0.0047 (11)0.0135 (11)
C160.0273 (12)0.0271 (10)0.0416 (13)0.0058 (8)0.0010 (10)0.0000 (9)
C210.0222 (10)0.0210 (9)0.0232 (10)0.0031 (7)0.0028 (8)0.0036 (7)
C220.0287 (12)0.0242 (10)0.0366 (12)0.0005 (8)0.0014 (10)0.0029 (8)
C230.0239 (12)0.0368 (12)0.0611 (18)0.0038 (9)0.0029 (12)0.0204 (12)
C240.0375 (14)0.0440 (13)0.0504 (16)0.0177 (11)0.0250 (12)0.0217 (12)
C250.0478 (15)0.0385 (12)0.0296 (12)0.0157 (11)0.0153 (11)0.0063 (10)
C260.0328 (12)0.0289 (10)0.0257 (11)0.0041 (8)0.0054 (9)0.0014 (8)
Geometric parameters (Å, º) top
Sn1—C212.109 (2)C15—H150.9500
Sn1—C112.113 (2)C16—H160.9500
Sn1—Br22.4710 (3)C21—C221.390 (3)
Sn1—Br12.4947 (3)C21—C261.392 (3)
C11—C161.386 (3)C22—C231.393 (3)
C11—C121.395 (3)C22—H220.9500
C12—C131.383 (3)C23—C241.387 (4)
C12—H120.9500C23—H230.9500
C13—C141.379 (4)C24—C251.375 (4)
C13—H130.9500C24—H240.9500
C14—C151.378 (4)C25—C261.378 (3)
C14—H140.9500C25—H250.9500
C15—C161.388 (3)C26—H260.9500
C21—Sn1—C11123.53 (8)C11—C16—C15119.8 (2)
C21—Sn1—Br2107.70 (5)C11—C16—H16120.1
C11—Sn1—Br2109.12 (6)C15—C16—H16120.1
C21—Sn1—Br1105.46 (5)C22—C21—C26119.8 (2)
C11—Sn1—Br1106.33 (5)C22—C21—Sn1120.90 (15)
Br2—Sn1—Br1102.741 (9)C26—C21—Sn1119.26 (15)
C16—C11—C12120.1 (2)C21—C22—C23119.1 (2)
C16—C11—Sn1120.48 (15)C21—C22—H22120.4
C12—C11—Sn1119.44 (16)C23—C22—H22120.4
C13—C12—C11119.4 (2)C24—C23—C22120.3 (2)
C13—C12—H12120.3C24—C23—H23119.9
C11—C12—H12120.3C22—C23—H23119.9
C14—C13—C12120.4 (2)C25—C24—C23120.4 (2)
C14—C13—H13119.8C25—C24—H24119.8
C12—C13—H13119.8C23—C24—H24119.8
C15—C14—C13120.4 (2)C24—C25—C26119.8 (2)
C15—C14—H14119.8C24—C25—H25120.1
C13—C14—H14119.8C26—C25—H25120.1
C14—C15—C16120.0 (2)C25—C26—C21120.6 (2)
C14—C15—H15120.0C25—C26—H26119.7
C16—C15—H15120.0C21—C26—H26119.7

Experimental details

Crystal data
Chemical formula[SnBr2(C6H5)2]
Mr432.71
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)8.9553 (5), 8.7468 (5), 17.0671 (8)
β (°) 99.713 (2)
V3)1317.71 (12)
Z4
Radiation typeMo Kα
µ (mm1)7.97
Crystal size (mm)0.23 × 0.17 × 0.13
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.262, 0.419
No. of measured, independent and
observed [I > 2σ(I)] reflections
46736, 3182, 2856
Rint0.031
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.017, 0.039, 1.05
No. of reflections3182
No. of parameters138
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.48

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006) and Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
Sn1—C212.109 (2)Sn1—Br22.4710 (3)
Sn1—C112.113 (2)Sn1—Br12.4947 (3)
C21—Sn1—C11123.53 (8)C21—Sn1—Br1105.46 (5)
C21—Sn1—Br2107.70 (5)C11—Sn1—Br1106.33 (5)
C11—Sn1—Br2109.12 (6)Br2—Sn1—Br1102.741 (9)
 

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