supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

bt2945 scheme

Acta Cryst. (2009). E65, m630    [ doi:10.1107/S1600536809016687 ]

Dipyridinium tribromidochloridobis(4-chlorophenyl)stannate(IV)

K. M. Lo and S. W. Ng

Abstract top

The tin atom in the substituted ammonium stannate(IV), (C5H6N)2[SnBr3(C6H4Cl)2Cl], lies on a center of symmetry in a distorted octahedral coordination geometry. Each independent halogen site is occupied by bromine and chlorine anions in an approximate 3:1 ratio. The pyridinium cation forms a hydrogen bond to only one of the halogen atoms.

Comment top

(type here to add)

Related literature top

For bis(4-dimethylaminopyridinium) tetrahalidodiorganostannates, see: Lo & Ng (2008a,b); Yap et al. (2008).

Experimental top

Bis(4-chlorophenyl)tin dichloride (0.40 g, 1 mol) and pyridine hydrobromide perbromide (0.64 g, 2 mmol) were heated in chloroform for 3 h. Crystals separated from the cool solution after a day.

Refinement top

Hydrogen atoms were placed in calculated positions (C—H 0.95, N–H 0.88 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C,N).

Each of the two independent tin-bound halogen atoms is a mixture of chlorine and bromine; as the total occupancy of chlorine refined to nearly 0.5 and that of bromine to nearly 1.5, these values were fixed as 0.5 and 1.5. Furthermore, the different halogen atoms sharing the same site were constrained to have the same coordinates and the same anisotropic displacement parameters. The final difference Fourier map did not have large peaks/deep holes near the disordered atoms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. 70% Probability anisotropic displacement ellipsoid plot of the ion-pair 2(C5H6 N) [SnBr3Cl(C6H4Cl)2]. Hydrogen atoms are drawn as spheres of arbitrary radius. Dashed lines denote hydrogen bonds. The tin-bound halogen atoms are disordered.
Dipyridinium tribromidochloridobis(4-chlorophenyl)stannate(IV) top
Crystal data top
(C5H6N)2[SnBr3(C6H4Cl)2Cl]F000 = 1488
Mr = 777.17Dx = 2.042 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 6664 reflections
a = 11.5130 (2) Åθ = 2.5–28.3º
b = 11.7139 (2) ŵ = 6.08 mm−1
c = 18.7748 (3) ÅT = 100 K
β = 93.230 (1)ºPrism, brown
V = 2527.99 (7) Å30.27 × 0.19 × 0.12 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		2903 independent reflections
Radiation source: fine-focus sealed tube2668 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.022
T = 100 Kθmax = 27.5º
ω scansθmin = 2.2º
Absorption correction: Multi-scan
(SADABS; Sheldrick, 1996)		h = −14→14
Tmin = 0.327, Tmax = 0.529k = −15→15
11728 measured reflectionsl = −23→24
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.018H-atom parameters constrained
wR(F2) = 0.047  w = 1/[σ2(Fo2) + (0.0246P)2 + 3.4843P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
2903 reflectionsΔρmax = 0.39 e Å−3
146 parametersΔρmin = −0.83 e Å−3
4 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
(C5H6N)2[SnBr3(C6H4Cl)2Cl]V = 2527.99 (7) Å3
Mr = 777.17Z = 4
Monoclinic, C2/cMo Kα
a = 11.5130 (2) ŵ = 6.08 mm−1
b = 11.7139 (2) ÅT = 100 K
c = 18.7748 (3) Å0.27 × 0.19 × 0.12 mm
β = 93.230 (1)º
Data collection top
Bruker SMART APEX
diffractometer		2903 independent reflections
Absorption correction: Multi-scan
(SADABS; Sheldrick, 1996)		2668 reflections with I > 2σ(I)
Tmin = 0.327, Tmax = 0.529Rint = 0.022
11728 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0184 restraints
wR(F2) = 0.047H-atom parameters constrained
S = 1.02Δρmax = 0.39 e Å−3
2903 reflectionsΔρmin = −0.83 e Å−3
146 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.50000.50000.50000.01196 (6)
Br10.308690 (19)0.509165 (19)0.578153 (12)0.01383 (8)0.7365 (11)
Br20.551744 (19)0.288797 (18)0.550827 (12)0.01450 (7)0.7635 (11)
Cl1'0.308690 (19)0.509165 (19)0.578153 (12)0.01383 (8)0.2635 (11)
Cl2'0.551744 (19)0.288797 (18)0.550827 (12)0.01450 (7)0.2365 (11)
Cl10.83429 (5)0.71755 (5)0.76748 (3)0.02688 (12)
N10.15868 (16)0.59124 (16)0.43101 (10)0.0217 (4)
H10.22060.58910.46070.026*
C10.60325 (16)0.57206 (16)0.58772 (10)0.0129 (4)
C20.60187 (18)0.52532 (17)0.65598 (11)0.0165 (4)
H20.55220.46260.66440.020*
C30.67258 (18)0.56972 (18)0.71184 (11)0.0188 (4)
H30.67160.53790.75840.023*
C40.74442 (17)0.66121 (18)0.69830 (11)0.0182 (4)
C50.74654 (17)0.70998 (17)0.63157 (11)0.0171 (4)
H50.79610.77290.62340.021*
C60.67469 (17)0.66515 (17)0.57641 (11)0.0155 (4)
H60.67450.69870.53030.019*
C70.0884 (2)0.50083 (18)0.42776 (13)0.0225 (5)
H70.10480.43660.45750.027*
C8−0.0077 (2)0.50100 (18)0.38125 (13)0.0235 (5)
H8−0.05790.43660.37770.028*
C9−0.03042 (19)0.5968 (2)0.33953 (12)0.0238 (5)
H9−0.09710.59880.30740.029*
C100.0440 (2)0.68937 (19)0.34465 (12)0.0231 (5)
H100.02900.75520.31610.028*
C110.13982 (19)0.68517 (19)0.39135 (12)0.0224 (5)
H110.19200.74790.39550.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01296 (10)0.01329 (10)0.00948 (10)−0.00098 (6)−0.00070 (7)0.00034 (7)
Br10.01297 (12)0.01610 (12)0.01249 (13)−0.00044 (8)0.00142 (9)0.00093 (8)
Br20.01749 (12)0.01242 (11)0.01334 (12)0.00098 (8)−0.00136 (8)0.00188 (8)
Cl1'0.01297 (12)0.01610 (12)0.01249 (13)−0.00044 (8)0.00142 (9)0.00093 (8)
Cl2'0.01749 (12)0.01242 (11)0.01334 (12)0.00098 (8)−0.00136 (8)0.00188 (8)
Cl10.0254 (3)0.0349 (3)0.0193 (3)−0.0073 (2)−0.0073 (2)−0.0056 (2)
N10.0177 (9)0.0277 (10)0.0190 (9)0.0050 (7)−0.0038 (7)−0.0047 (8)
C10.0126 (9)0.0155 (9)0.0103 (9)0.0020 (7)−0.0011 (7)−0.0014 (7)
C20.0160 (9)0.0177 (9)0.0156 (10)−0.0017 (7)0.0004 (8)−0.0001 (8)
C30.0221 (10)0.0222 (10)0.0119 (9)0.0010 (8)−0.0016 (8)0.0022 (8)
C40.0153 (10)0.0237 (10)0.0150 (10)0.0002 (8)−0.0041 (8)−0.0054 (8)
C50.0155 (9)0.0170 (9)0.0188 (10)−0.0028 (7)0.0002 (8)−0.0013 (8)
C60.0154 (9)0.0170 (9)0.0142 (10)0.0012 (7)0.0018 (7)0.0010 (8)
C70.0251 (12)0.0223 (11)0.0204 (12)0.0064 (8)0.0055 (9)0.0023 (9)
C80.0194 (11)0.0239 (11)0.0276 (13)−0.0015 (8)0.0062 (9)−0.0024 (9)
C90.0173 (10)0.0332 (12)0.0204 (11)0.0049 (9)−0.0028 (8)−0.0028 (9)
C100.0280 (11)0.0214 (10)0.0201 (11)0.0058 (9)0.0029 (9)0.0019 (9)
C110.0251 (11)0.0196 (10)0.0225 (11)−0.0018 (8)0.0034 (9)−0.0048 (9)
Geometric parameters (Å, °) top
Sn1—C1i2.149 (2)C3—C41.386 (3)
Sn1—C12.149 (2)C3—H30.9500
Sn1—Br12.7166 (2)C4—C51.378 (3)
Sn1—Cl2'i2.7060 (2)C5—C61.391 (3)
Sn1—Br2i2.7060 (2)C5—H50.9500
Sn1—Br22.7060 (2)C6—H60.9500
Sn1—Cl1'i2.7166 (2)C7—C81.370 (3)
Sn1—Br1i2.7166 (2)C7—H70.9500
Cl1—C41.744 (2)C8—C91.384 (3)
N1—C71.332 (3)C8—H80.9500
N1—C111.339 (3)C9—C101.383 (3)
N1—H10.8800C9—H90.9500
C1—C61.389 (3)C10—C111.371 (3)
C1—C21.394 (3)C10—H100.9500
C2—C31.392 (3)C11—H110.9500
C2—H20.9500
C1i—Sn1—C1180.000 (1)C6—C1—Sn1119.86 (14)
C1i—Sn1—Cl2'i89.29 (5)C2—C1—Sn1121.05 (14)
C1—Sn1—Cl2'i90.71 (5)C3—C2—C1120.63 (19)
C1i—Sn1—Br2i89.29 (5)C3—C2—H2119.7
C1—Sn1—Br2i90.71 (5)C1—C2—H2119.7
Cl2'i—Sn1—Br2i0.000 (13)C4—C3—C2118.71 (19)
C1i—Sn1—Br290.71 (5)C4—C3—H3120.6
C1—Sn1—Br289.29 (5)C2—C3—H3120.6
Cl2'i—Sn1—Br2180.0C5—C4—C3121.90 (19)
Br2i—Sn1—Br2180.0C5—C4—Cl1118.68 (16)
C1i—Sn1—Cl1'i90.05 (5)C3—C4—Cl1119.41 (17)
C1—Sn1—Cl1'i89.95 (5)C4—C5—C6118.67 (19)
Cl2'i—Sn1—Cl1'i90.845 (7)C4—C5—H5120.7
Br2i—Sn1—Cl1'i90.845 (7)C6—C5—H5120.7
Br2—Sn1—Cl1'i89.155 (7)C5—C6—C1120.98 (19)
C1i—Sn1—Br1i90.05 (5)C5—C6—H6119.5
C1—Sn1—Br1i89.95 (5)C1—C6—H6119.5
Cl2'i—Sn1—Br1i90.845 (7)N1—C7—C8119.7 (2)
Br2i—Sn1—Br1i90.845 (7)N1—C7—H7120.2
Br2—Sn1—Br1i89.155 (7)C8—C7—H7120.2
Cl1'i—Sn1—Br1i0.000 (8)C7—C8—C9118.8 (2)
C1i—Sn1—Br189.95 (5)C7—C8—H8120.6
C1—Sn1—Br190.05 (5)C9—C8—H8120.6
Cl2'i—Sn1—Br189.155 (7)C8—C9—C10120.0 (2)
Br2i—Sn1—Br189.155 (7)C8—C9—H9120.0
Br2—Sn1—Br190.845 (7)C10—C9—H9120.0
Cl1'i—Sn1—Br1180.0C11—C10—C9119.3 (2)
Br1i—Sn1—Br1180.0C11—C10—H10120.3
C7—N1—C11123.26 (19)C9—C10—H10120.3
C7—N1—H1118.4N1—C11—C10119.0 (2)
C11—N1—H1118.4N1—C11—H11120.5
C6—C1—C2119.08 (18)C10—C11—H11120.5
Cl2'i—Sn1—C1—C6−40.72 (15)C1—C2—C3—C4−0.1 (3)
Br2i—Sn1—C1—C6−40.72 (15)C2—C3—C4—C50.9 (3)
Br2—Sn1—C1—C6139.28 (15)C2—C3—C4—Cl1−179.64 (16)
Cl1'i—Sn1—C1—C650.12 (15)C3—C4—C5—C6−0.4 (3)
Br1i—Sn1—C1—C650.12 (15)Cl1—C4—C5—C6−179.89 (15)
Br1—Sn1—C1—C6−129.88 (15)C4—C5—C6—C1−0.9 (3)
Cl2'i—Sn1—C1—C2140.70 (15)C2—C1—C6—C51.7 (3)
Br2i—Sn1—C1—C2140.70 (15)Sn1—C1—C6—C5−176.91 (15)
Br2—Sn1—C1—C2−39.30 (15)C11—N1—C7—C81.0 (3)
Cl1'i—Sn1—C1—C2−128.46 (15)N1—C7—C8—C9−1.2 (3)
Br1i—Sn1—C1—C2−128.46 (15)C7—C8—C9—C100.8 (3)
Br1—Sn1—C1—C251.54 (15)C8—C9—C10—C11−0.1 (3)
C6—C1—C2—C3−1.2 (3)C7—N1—C11—C10−0.3 (3)
Sn1—C1—C2—C3177.39 (15)C9—C10—C11—N1−0.1 (3)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Br10.882.553.317 (2)146
Table 1
Selected geometric parameters (Å) top
Sn1—C12.149 (2)Sn1—Br22.7060 (2)
Sn1—Br12.7166 (2)
Acknowledgements top

We thank the University of Malaya for funding this study (RG020/09AFR).

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Lo, K. M. & Ng, S. W. (2008a). Acta Cryst. E64, m800.

Lo, K. M. & Ng, S. W. (2008b). Acta Cryst. E64, m834.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.

Yap, Q. L., Lo, K. M. & Ng, S. W. (2008). Acta Cryst. E64, m696.