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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 6| June 2008| Pages m749-m750
doi:10.1107/S1600536808012129

Bis(2-bromo­pyridinium) hexa­bromido­stannate(IV)

Basem Fares Ali,a Rawhi H. Al-Farb* and Salim F. Haddadc

aDepartment of Chemistry, Al al-Bayt University, Mafraq 25113, Jordan, bFaculty of Information Technology and Science, Al-Balqa'a Applied University, Salt, Jordan, and cDepartment of Chemistry, The University of Jordan, Amman, Jordan
*Correspondence e-mail: rohi@bau.edu.jo

(Received 10 April 2008; accepted 26 April 2008; online 3 May 2008)

The asymmetric unit of the title compound, (C5H5BrN)2[SnBr6], contains one cation and one half-anion. The [SnBr6]2− anion is located on an inversion center and forms a quasi-regular octa­hedral arrangement. The crystal structure consists of two-dimensional supra­molecular layers assembled via hydrogen-bonding inter­actions of N—H⋯Br—Sn [D⋯A = 3.375 (13)–3.562 (13) Å and D—H⋯A = 127–142°, along with C—Br⋯Br synthons [3.667 (2) and 3.778 (3) Å]. These layers are parallel to the bc plane and built up from anions inter­acting extensively with the six surrounding cations.

Related literature

The title salt is isomorphous with the Te analogue (Fernandes et al., 2004[Fernandes, R. M. Jr, de Oliveira, G. M., Lang, E. S. & Vázquez-López, E. M. (2004). Z. Anorg. Allg. Chem. 630, 2687-2691.]). For related literature, see: Al-Far & Ali (2007[Al-Far, R. & Ali, B. F. (2007). Acta Cryst. C63, m137-m139.]); Ali, Al-Far & Al-Sou'od (2007[Ali, B. F., Al-Far, R. & Al-Sou'od, K. (2007). J. Chem. Crystallogr. 37, 265-273.]); Ali & Al-Far (2007[Ali, B. F. & Al-Far, R. (2007). Acta Cryst. E63, m892-m894.]); Ali, Al-Far & Ng (2007[Ali, B. F., Al-Far, R. & Ng, S. W. (2007). Acta Cryst. E63, m2102-m2103.]); Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]); Aruta et al. (2005[Aruta, C., Licci, F., Zappettini, A., Bolzoni, F., Rastelli, F., Ferro, P. & Besagni, T. (2005). Appl. Phys. A, 81, 963-968.]); Hill (1998[Hill, C. L. (1998). Chem. Rev. 98, 1-2.]); Kagan et al. (1999[Kagan, C. R., Mitzi, D. B. & Dimitrakopoulos, C. D. (1999). Science, 286, 945-947.]); Knutson et al. (2005[Knutson, J. L., Martin, J. D. & Mitzi, D. B. (2005). Inorg. Chem. 44, 4699-4705.]); Raptopoulou et al. (2002[Raptopoulou, C. P., Terzis, A., Mousdis, G. A. & Papavassiliou, G. C. (2002). Z. Naturforsch. Teil B, 57, 645-650.]); Tudela & Khan (1991[Tudela, D. & Khan, M. A. (1991). J. Chem. Soc. Dalton Trans. pp. 1003-1006.]); Willey et al. (1998[Willey, G. R., Woodman, T. J., Somasundaram, U., Aris, D. R. & Errington, W. (1998). J. Chem. Soc. Dalton Trans. pp. 2573-2576.]).

[Scheme 1]

Experimental

Crystal data

  • (C5H5BrN)2[SnBr6]

  • Mr = 916.12

  • Triclinic, [P \overline 1]

  • a = 7.4037 (15) Å

  • b = 8.3393 (17) Å

  • c = 9.4302 (19) Å

  • α = 73.14 (3)°

  • β = 67.98 (3)°

  • γ = 82.44 (3)°

  • V = 516.4 (2) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 16.71 mm−1

  • T = 293 (2) K

  • 0.16 × 0.13 × 0.08 mm
Data collection

  • Bruker–Siemens SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). SADABS. Bruker AXS, Madison, Wisconsin, USA.]) Tmin = 0.058, Tmax = 0.261

  • 2266 measured reflections

  • 1807 independent reflections

  • 1308 reflections with I > 2σ(I)

  • Rint = 0.091
Refinement

  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.178

  • S = 1.02

  • 1807 reflections

  • 67 parameters

  • H-atom parameters constrained

  • Δρmax = 3.31 e Å−3

  • Δρmin = −1.87 e Å−3

Table 1
Selected geometric parameters (Å, °)

Sn1—Br3 2.5939 (15)
Sn1—Br1 2.6027 (15)
Sn1—Br4 2.6174 (17)
Br3—Sn1—Br1 89.06 (5)
Br3i—Sn1—Br1 90.94 (5)
Br3—Sn1—Br4i 89.43 (6)
Br1—Sn1—Br4i 90.21 (5)
Br3—Sn1—Br4 90.57 (6)
Br1—Sn1—Br4 89.79 (5)
Symmetry code: (i) -x+1, -y+1, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯Br4ii 0.86 2.65 3.375 (13) 142
N1—H1⋯Br1iii 0.86 2.98 3.562 (13) 127
Symmetry codes: (ii) -x+2, -y+1, -z-1; (iii) -x+1, -y+1, -z-1.

Data collection: SMART (Bruker, 2006[Bruker (2006). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2006[Bruker (2006). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: XS in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: XL in SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: XCIF in SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012129/bx2139sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012129/bx2139Isup2.hkl

checkCIF report


Comment top

Noncovalent interactions play an important role in organizing structural units in both natural and artificial systems. Hybrid organic-inorganic compounds are of great interest owing to their ionic, electrical, magnetic and optical properties (Hill, 1998; Kagan et al., 1999; Raptopoulou et al., 2002). Tin metal-halo based hybrids are of particular interest as being materials with interesting optical and magnetic properties (Aruta et al., 2005; Knutson et al., 2005; Kagan et al., 1999). We are currently carrying out studies about lattice including different types of intermolecular interactions (aryl···aryl, X···X, X···aryl and X···H). Within our research of hybrid compounds containing tin metal (Al-Far & Ali 2007; Ali, Al-Far & Al-Sou'od, 2007; Ali & Al-Far, 2007; Ali, Al-Far & Ng, 2007), the crystal structure of the title salt, (I), has been investigated.

The asymmetric unit of (I) contains one cation and one-half anion (Fig. 1). The whole (2-Br—C5H5N)2[SnBr6] geometry is generated through an inversion center with tin being lying on the special crystallographic position of (1/2, 1/2, 0). The (SnBr6)2- anion forms a quasi-octahedral geometry (Table 1), with the Sn—Br bond lengths are almost invariant. These lengths are in accordance with tin-bromide distances reported for (SnBr6)2- anion containing compounds (Willey et al.,1998; Tudela & Khan 1991; Al-Far & Ali 2007; Ali, Al-Far & Al-Sou'od, 2007; Ali & Al-Far, 2007; Ali, Al-Far & Ng, 2007). Bond lengths and angles within the cation are as expected (Allen et al., 1987).

The packing of the structure (Fig. 2) can be described as layers of alternating anions and cations parallel to bc plane. In these layers each (SnBr6)2- anion is interacting with six cations via two N—H···Br interactions (Table 2) and the symmetry related ones along with two Br···Br interactions and symmetry related ones [Br2···Br4and Br2···Br1of 3.6666 (23) and 3.7779 (29) Å, respectively; Fig. 2].

The N—H···N interactions along with C—Br···Br synthons are potential building blocks for this stable supramolecular lattice. The stability of this lattice is evident in the isostructurality with the reported Te analogue (Fernandes et al., 2004).

Related literature top

The title salt is isomorphous with the Te-analogue, see: Fernandes et al. (2004). For related literature, see: Al-Far & Ali (2007); Ali, Al-Far & Al-Sou'od (2007); Ali & Al-Far (2007); Ali, Al-Far & Ng (2007); Allen et al. (1987); Aruta et al. (2005); Hill (1998); Kagan et al. (1999); Knutson et al. (2005); Raptopoulou et al. (2002); Tudela & Khan (1991); Willey et al. (1998).

Experimental top

Warm solution of Sn metal (1.0 mmol) dissolved in absolute ethanol (10 ml) and HBr (60%, 5 ml), was added dropwise to a stirred hot solution of 2-bromopyridine (2 mmol) dissolved in ethanol (10 ml). The mixture was then treated with liquid Br2 (2 ml) and refluxed for 3/2 h. The resulting mixture was then filtered off, and allowed to stand undisturbed at room temperature. The salt crystallized over 1 d as nice yellow block crystals (yield: 83%).

Refinement top

H atoms were positioned geometrically, with N—H = 0.86 Å (for NH) and C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C, N).

Computing details top

Data collection: SMART (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2006); data reduction: SAINT-Plus (Bruker, 2006); program(s) used to solve structure: XS in SHELXTL (Sheldrick, 2008); program(s) used to refine structure: XL in SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XCIF in SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the asymmetric unit of (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram of (I). Hydrogen bonds (dashed lines) and Br···Br interactions (thick dashed lines) are shown for (SnBr6)2- anions and six surrounding cations.
Bis(2-bromopyridinium) hexabromidostannate(IV) top
Crystal data top
(C5H5BrN)2[SnBr6]Z = 1
Mr = 916.12F(000) = 414
Triclinic, P1Dx = 2.946 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4037 (15) ÅCell parameters from 255 reflections
b = 8.3393 (17) Åθ = 2.1–27.7°
c = 9.4302 (19) ŵ = 16.71 mm−1
α = 73.14 (3)°T = 293 K
β = 67.98 (3)°Block, yellow
γ = 82.44 (3)°0.16 × 0.13 × 0.08 mm
V = 516.4 (2) Å3
Data collection top
Bruker–Siemens SMART APEX
diffractometer		1807 independent reflections
Radiation source: fine-focus sealed tube1308 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.091
Detector resolution: 8.3 pixels mm-1θmax = 25.0°, θmin = 2.4°
ω scansh = −1→8
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		k = −9→9
Tmin = 0.058, Tmax = 0.261l = −10→11
2266 measured reflections
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1076P)2 + 1.002P]
where P = (Fo2 + 2Fc2)/3
1807 reflections(Δ/σ)max < 0.001
67 parametersΔρmax = 3.31 e Å−3
0 restraintsΔρmin = −1.87 e Å−3
Crystal data top
(C5H5BrN)2[SnBr6]γ = 82.44 (3)°
Mr = 916.12V = 516.4 (2) Å3
Triclinic, P1Z = 1
a = 7.4037 (15) ÅMo Kα radiation
b = 8.3393 (17) ŵ = 16.71 mm−1
c = 9.4302 (19) ÅT = 293 K
α = 73.14 (3)°0.16 × 0.13 × 0.08 mm
β = 67.98 (3)°
Data collection top
Bruker–Siemens SMART APEX
diffractometer		1807 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		1308 reflections with I > 2σ(I)
Tmin = 0.058, Tmax = 0.261Rint = 0.091
2266 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.178H-atom parameters constrained
S = 1.02Δρmax = 3.31 e Å−3
1807 reflectionsΔρmin = −1.87 e Å−3
67 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
Sn10.50000.50000.00000.0271 (4)
Br40.80819 (19)0.51691 (17)−0.25738 (17)0.0365 (4)
Br30.5601 (2)0.17999 (16)0.09614 (18)0.0394 (4)
Br10.2879 (2)0.43877 (19)−0.14375 (19)0.0426 (4)
Br20.6761 (3)0.2489 (2)−0.4484 (2)0.0674 (6)
C20.7936 (19)0.1051 (18)−0.5793 (18)0.038 (3)*
N10.9316 (17)0.1687 (17)−0.7225 (17)0.049 (3)*
H10.95750.2732−0.74990.059*
C30.751 (2)−0.0578 (18)−0.5321 (19)0.042 (3)*
H30.6604−0.1039−0.43240.051*
C40.845 (2)−0.155 (2)−0.6371 (19)0.047 (4)*
H40.8119−0.2665−0.60940.057*
C50.990 (2)−0.090 (2)−0.784 (2)0.051 (4)*
H51.0572−0.1560−0.85260.061*
C61.028 (3)0.077 (2)−0.822 (2)0.060 (5)*
H61.12250.1254−0.91830.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0304 (6)0.0249 (6)0.0213 (7)0.0021 (5)−0.0058 (5)−0.0048 (5)
Br40.0387 (7)0.0322 (7)0.0294 (8)−0.0003 (5)−0.0011 (6)−0.0094 (6)
Br30.0462 (8)0.0258 (7)0.0340 (9)0.0066 (6)−0.0067 (6)−0.0034 (6)
Br10.0491 (8)0.0446 (8)0.0391 (9)−0.0002 (6)−0.0226 (7)−0.0094 (7)
Br20.1089 (15)0.0522 (10)0.0491 (11)0.0059 (10)−0.0295 (11)−0.0268 (9)
Geometric parameters (Å, º) top
Sn1—Br32.5939 (15)N1—C61.32 (2)
Sn1—Br3i2.5939 (15)N1—H10.8600
Sn1—Br12.6027 (15)C3—C41.39 (2)
Sn1—Br1i2.6027 (15)C3—H30.9300
Sn1—Br4i2.6174 (17)C4—C51.40 (2)
Sn1—Br42.6174 (17)C4—H40.9300
Br2—C21.870 (15)C5—C61.37 (2)
C2—C31.34 (2)C5—H50.9300
C2—N11.357 (19)C6—H60.9300
Br3—Sn1—Br3i180.0N1—C2—Br2117.9 (11)
Br3—Sn1—Br189.06 (5)C6—N1—C2122.7 (14)
Br3i—Sn1—Br190.94 (5)C6—N1—H1118.6
Br3—Sn1—Br1i90.94 (5)C2—N1—H1118.6
Br3i—Sn1—Br1i89.06 (5)C2—C3—C4117.8 (15)
Br1—Sn1—Br1i180.00 (5)C2—C3—H3121.1
Br3—Sn1—Br4i89.43 (6)C4—C3—H3121.1
Br3i—Sn1—Br4i90.57 (6)C3—C4—C5121.7 (15)
Br1—Sn1—Br4i90.21 (5)C3—C4—H4119.1
Br1i—Sn1—Br4i89.79 (5)C5—C4—H4119.1
Br3—Sn1—Br490.57 (6)C6—C5—C4116.8 (17)
Br3i—Sn1—Br489.43 (6)C6—C5—H5121.6
Br1—Sn1—Br489.79 (5)C4—C5—H5121.6
Br1i—Sn1—Br490.21 (5)N1—C6—C5120.6 (17)
Br4i—Sn1—Br4180.0N1—C6—H6119.7
C3—C2—N1120.3 (15)C5—C6—H6119.7
C3—C2—Br2121.8 (12)
C3—C2—N1—C61 (2)C2—C3—C4—C54 (2)
Br2—C2—N1—C6177.7 (12)C3—C4—C5—C6−3 (2)
N1—C2—C3—C4−3 (2)C2—N1—C6—C51 (3)
Br2—C2—C3—C4−179.9 (11)C4—C5—C6—N10 (3)
Symmetry code: (i) −x+1, −y+1, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Br4ii0.862.653.375 (13)142
N1—H1···Br1iii0.862.983.562 (13)127
Symmetry codes: (ii) −x+2, −y+1, −z−1; (iii) −x+1, −y+1, −z−1.

Experimental details

Crystal data
Chemical formula(C5H5BrN)2[SnBr6]
Mr916.12
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.4037 (15), 8.3393 (17), 9.4302 (19)
α, β, γ (°)73.14 (3), 67.98 (3), 82.44 (3)
V (Å3)516.4 (2)
Z1
Radiation typeMo Kα
µ (mm−1)16.71
Crystal size (mm)0.16 × 0.13 × 0.08
Data collection
DiffractometerBruker–Siemens SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.058, 0.261
No. of measured, independent and
observed [I > 2σ(I)] reflections		2266, 1807, 1308
Rint0.091
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.178, 1.02
No. of reflections1807
No. of parameters67
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)3.31, −1.87

Computer programs: SMART (Bruker, 2006), SAINT-Plus (Bruker, 2006), XS in SHELXTL (Sheldrick, 2008), XL in SHELXTL (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), XCIF in SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
Sn1—Br32.5939 (15)Sn1—Br42.6174 (17)
Sn1—Br12.6027 (15)
Br3—Sn1—Br189.06 (5)Br1—Sn1—Br4i90.21 (5)
Br3i—Sn1—Br190.94 (5)Br3—Sn1—Br490.57 (6)
Br3—Sn1—Br4i89.43 (6)Br1—Sn1—Br489.79 (5)
Symmetry code: (i) −x+1, −y+1, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Br4ii0.862.653.375 (13)142.4
N1—H1···Br1iii0.862.983.562 (13)126.5
Symmetry codes: (ii) −x+2, −y+1, −z−1; (iii) −x+1, −y+1, −z−1.
 

Acknowledgements

Al al-Bayt University and Al-Balqa'a Applied University are thanked for supporting this work

References

First citationAl-Far, R. & Ali, B. F. (2007). Acta Cryst. C63, m137–m139.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationAli, B. F. & Al-Far, R. (2007). Acta Cryst. E63, m892–m894.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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 First citationWilley, G. R., Woodman, T. J., Somasundaram, U., Aris, D. R. & Errington, W. (1998). J. Chem. Soc. Dalton Trans. pp. 2573–2576.  Web of Science CSD CrossRef Google Scholar

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ISSN: 2056-9890
Volume 64| Part 6| June 2008| Pages m749-m750
doi:10.1107/S1600536808012129
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