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Acta Cryst. (2009). E65, m716    [ doi:10.1107/S1600536809019758 ]

Di-[mu]-hydroxido-bis[bromidodi-p-tolyltin(IV)]

K. M. Lo and S. W. Ng

Abstract top

The Sn atoms in the dinuclear title compound, [Sn2Br2(C7H7)4(OH)2], exist in distorted trigonal-bipyramidal BrSnC2O2 coordination geometries. Each of the two independent dinuclear molecules comprising the asymmetric unit is disposed about a center of inversion. In the crystal, molecules are linked by an O-H... hydrogen bond.

Related literature top

For other dihalo-di-µ-hydoxotetraorganylditins, see: Anacona et al. (2003); Barba et al. (2007); Puff et al. (1984).

Experimental top

Di(p-tolyl)dimethyltin was synthesized by a Grignard reaction. This compound (3.37 g, 10 mmol) and pyridinium tribromide (3.19 g, 10 mmol) were heated in an ethanol/chloroform mixture for 1 hour. The solution was set aside for the growth of crystals. The organic reactant probably cleaved the two tin-methyl bonds to form di(p-tolyl)tin dibromide, which then underwent hydrolysis to the title compound.

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.98 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5 times Ueq(C). The hydroxyl H-atom was similarly treated; O—H 0.84 Å and U(H) set to 1.2 times Ueq(O).

The final difference Fourier map had a large peaks/deep holes at approximately 1 Å from Sn2 but was otherwise featureless.

The plate-like nature of the crystal, along with the presence of heavy atoms, adversedly affected the quality of the diffraction data. As some of the displacement ellipsoids were rather elongated, the refinement strategy was to restrain the anisotropic displacement parameters of all carbon and oxygen atoms to be nearly isotropic.

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. Thermal ellipsoid plot (Barbour, 2001) of one independent molecule of Sn2Br2(OH)2(C7H7)4 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Thermal ellipsoid plot (Barbour, 2001) of the second independent molecule of Sn2Br2(OH)2(C7H7)4at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Di-µ-hydroxido-bis[bromidodi-p-tolyltin(IV)] top
Crystal data top
[Sn2Br2(C7H7)4(OH)2]Z = 2
Mr = 795.72F(000) = 768
Triclinic, P1Dx = 1.887 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.9971 (3) ÅCell parameters from 3015 reflections
b = 11.5391 (3) Åθ = 2.2–28.0°
c = 12.1969 (3) ŵ = 4.66 mm−1
α = 77.092 (2)°T = 100 K
β = 86.552 (2)°Plate, colorless
γ = 68.204 (2)°0.35 × 0.05 × 0.05 mm
V = 1400.34 (6) Å3
Data collection top
Bruker SMART APEX
diffractometer		4871 independent reflections
Radiation source: fine-focus sealed tube3367 reflections with I > 2σ(I)
graphiteRint = 0.056
ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.292, Tmax = 0.800k = −12→13
9026 measured reflectionsl = −14→14
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)] = 0.076Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.227H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1452P)2]
where P = (Fo2 + 2Fc2)/3
4871 reflections(Δ/σ)max = 0.001
311 parametersΔρmax = 2.96 e Å−3
180 restraintsΔρmin = −3.19 e Å−3
Crystal data top
[Sn2Br2(C7H7)4(OH)2]γ = 68.204 (2)°
Mr = 795.72V = 1400.34 (6) Å3
Triclinic, P1Z = 2
a = 10.9971 (3) ÅMo Kα radiation
b = 11.5391 (3) ŵ = 4.66 mm−1
c = 12.1969 (3) ÅT = 100 K
α = 77.092 (2)°0.35 × 0.05 × 0.05 mm
β = 86.552 (2)°
Data collection top
Bruker SMART APEX
diffractometer		4871 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3367 reflections with I > 2σ(I)
Tmin = 0.292, Tmax = 0.800Rint = 0.056
9026 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.076H-atom parameters constrained
wR(F2) = 0.227Δρmax = 2.96 e Å−3
S = 1.05Δρmin = −3.19 e Å−3
4871 reflectionsAbsolute structure: ?
311 parametersFlack parameter: ?
180 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.62921 (7)0.55224 (9)0.51125 (6)0.0230 (3)
Sn20.64941 (7)0.38277 (9)0.05546 (6)0.0247 (3)
Br10.68040 (11)0.63918 (14)0.67783 (9)0.0280 (4)
Br20.67660 (12)0.23425 (14)0.25580 (10)0.0302 (4)
O10.4708 (7)0.5278 (8)0.5909 (6)0.0248 (19)
H10.44580.54530.65380.030*
O20.4555 (7)0.4658 (8)0.0890 (6)0.0244 (19)
H20.42060.44510.14960.029*
C10.5776 (11)0.7262 (12)0.3905 (10)0.024 (3)
C20.6189 (12)0.7250 (13)0.2814 (10)0.029 (3)
H2a0.66890.64690.25990.035*
C30.5850 (12)0.8423 (14)0.2031 (11)0.031 (3)
H30.61530.84160.12850.038*
C40.5107 (11)0.9574 (13)0.2283 (10)0.029 (3)
C50.4709 (12)0.9557 (13)0.3400 (10)0.029 (3)
H50.41971.03400.36060.034*
C60.5041 (11)0.8434 (13)0.4206 (10)0.028 (3)
H60.47770.84490.49600.033*
C70.4664 (13)1.0812 (15)0.1414 (11)0.039 (3)
H7A0.53651.08170.08790.058*
H7B0.44581.15300.17860.058*
H7C0.38811.08950.10110.058*
C80.8096 (11)0.3956 (13)0.5251 (10)0.026 (3)
C90.8241 (12)0.2834 (13)0.4902 (10)0.031 (3)
H90.74960.27430.46310.037*
C100.9453 (13)0.1859 (15)0.4946 (11)0.036 (3)
H100.95350.11070.47020.043*
C111.0547 (12)0.1972 (14)0.5344 (10)0.031 (3)
C121.0404 (13)0.3050 (15)0.5719 (12)0.040 (4)
H121.11430.31200.60250.048*
C130.9190 (13)0.4043 (16)0.5658 (12)0.041 (4)
H130.91170.47920.59010.049*
C141.1892 (13)0.0913 (16)0.5399 (13)0.045 (4)
H14A1.24570.12050.48440.067*
H14B1.18020.01550.52340.067*
H14C1.22820.06980.61540.067*
C150.7678 (11)0.4819 (14)0.0875 (10)0.028 (3)
C160.8608 (11)0.4277 (12)0.1749 (9)0.023 (3)
H160.86760.34920.22450.027*
C170.9444 (12)0.4905 (13)0.1889 (10)0.030 (3)
H171.00810.45280.24860.035*
C180.9376 (12)0.6030 (14)0.1205 (11)0.032 (3)
C190.8446 (12)0.6556 (15)0.0312 (11)0.035 (3)
H190.83850.7338−0.01860.042*
C200.7623 (12)0.5951 (13)0.0151 (10)0.031 (3)
H200.70100.6314−0.04630.037*
C211.0280 (13)0.6689 (15)0.1349 (12)0.040 (4)
H21A1.05360.70540.06090.060*
H21B1.10630.60700.17830.060*
H21C0.98330.73730.17510.060*
C220.7048 (11)0.2359 (13)−0.0370 (10)0.027 (3)
C230.6804 (12)0.2653 (14)−0.1532 (10)0.030 (3)
H230.62830.3495−0.19090.036*
C240.7342 (13)0.1684 (14)−0.2122 (10)0.033 (3)
H240.71310.1866−0.29010.039*
C250.8156 (13)0.0490 (15)−0.1629 (11)0.035 (3)
C260.8421 (13)0.0196 (15)−0.0484 (12)0.037 (3)
H260.8979−0.0639−0.01230.045*
C270.7869 (12)0.1125 (13)0.0126 (10)0.031 (3)
H270.80530.09180.09120.037*
C280.8804 (14)−0.0516 (15)−0.2323 (12)0.041 (4)
H28A0.9194−0.0147−0.29870.061*
H28B0.8146−0.0799−0.25630.061*
H28C0.9490−0.1248−0.18660.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0242 (4)0.0333 (6)0.0114 (4)−0.0063 (4)0.0016 (3)−0.0123 (4)
Sn20.0272 (5)0.0359 (6)0.0117 (4)−0.0082 (4)0.0011 (3)−0.0127 (4)
Br10.0312 (6)0.0416 (9)0.0135 (6)−0.0108 (6)0.0014 (5)−0.0155 (6)
Br20.0346 (7)0.0402 (9)0.0134 (6)−0.0085 (6)0.0002 (5)−0.0104 (6)
O10.027 (4)0.037 (5)0.012 (4)−0.009 (4)0.005 (3)−0.014 (4)
O20.024 (4)0.034 (5)0.014 (4)−0.007 (3)0.003 (3)−0.012 (3)
C10.025 (5)0.025 (6)0.017 (5)−0.002 (5)−0.005 (4)−0.004 (5)
C20.031 (6)0.031 (7)0.022 (6)−0.008 (5)−0.002 (4)−0.005 (5)
C30.033 (6)0.039 (7)0.023 (6)−0.010 (5)0.003 (5)−0.014 (5)
C40.029 (5)0.036 (7)0.022 (5)−0.007 (5)−0.005 (4)−0.014 (5)
C50.029 (5)0.034 (7)0.024 (6)−0.008 (5)−0.001 (4)−0.016 (5)
C60.029 (5)0.036 (7)0.016 (5)−0.005 (5)−0.001 (4)−0.013 (5)
C70.038 (6)0.046 (7)0.030 (6)−0.013 (5)0.000 (5)−0.009 (6)
C80.024 (5)0.036 (7)0.015 (5)−0.002 (5)0.004 (4)−0.014 (5)
C90.033 (6)0.033 (7)0.024 (6)−0.006 (5)−0.004 (5)−0.010 (5)
C100.043 (6)0.042 (7)0.026 (6)−0.011 (5)−0.002 (5)−0.020 (5)
C110.031 (6)0.040 (7)0.018 (5)−0.010 (5)0.002 (4)−0.005 (5)
C120.034 (6)0.051 (8)0.035 (6)−0.009 (5)−0.002 (5)−0.018 (6)
C130.038 (6)0.047 (8)0.042 (7)−0.015 (6)0.003 (5)−0.019 (6)
C140.042 (6)0.046 (8)0.040 (7)−0.005 (6)−0.001 (5)−0.014 (6)
C150.023 (5)0.040 (7)0.024 (6)−0.011 (5)0.005 (4)−0.018 (5)
C160.028 (5)0.025 (6)0.014 (5)−0.005 (5)0.001 (4)−0.011 (5)
C170.030 (5)0.039 (7)0.021 (5)−0.010 (5)0.004 (4)−0.017 (5)
C180.033 (6)0.038 (7)0.027 (6)−0.008 (5)0.009 (5)−0.019 (5)
C190.037 (6)0.041 (7)0.027 (6)−0.015 (5)0.003 (5)−0.008 (5)
C200.032 (6)0.041 (7)0.016 (5)−0.004 (5)−0.009 (4)−0.011 (5)
C210.040 (6)0.051 (8)0.036 (6)−0.020 (6)−0.003 (5)−0.016 (6)
C220.030 (5)0.032 (7)0.022 (5)−0.007 (5)−0.002 (4)−0.018 (5)
C230.038 (6)0.036 (7)0.014 (5)−0.010 (5)−0.003 (4)−0.009 (5)
C240.043 (6)0.036 (7)0.020 (5)−0.007 (5)−0.003 (5)−0.019 (5)
C250.041 (6)0.045 (7)0.025 (6)−0.014 (5)0.000 (5)−0.022 (5)
C260.034 (6)0.039 (7)0.037 (6)−0.009 (5)0.000 (5)−0.012 (6)
C270.043 (6)0.031 (7)0.016 (5)−0.008 (5)−0.007 (5)−0.009 (5)
C280.048 (6)0.044 (7)0.031 (6)−0.013 (6)0.005 (5)−0.021 (6)
Geometric parameters (Å, °) top
Sn1—O12.024 (8)C11—C141.523 (18)
Sn1—C82.115 (12)C12—C131.39 (2)
Sn1—C12.111 (12)C12—H120.9500
Sn1—O1i2.248 (8)C13—H130.9500
Sn1—Br12.6304 (14)C14—H14A0.9800
Sn2—O22.046 (8)C14—H14B0.9800
Sn2—C222.126 (13)C14—H14C0.9800
Sn2—C152.127 (13)C15—C201.386 (19)
Sn2—O2ii2.205 (8)C15—C161.390 (16)
Sn2—Br22.6141 (15)C16—C171.402 (18)
O1—Sn1i2.248 (8)C16—H160.9500
O1—H10.8400C17—C181.357 (19)
O2—Sn2ii2.205 (8)C17—H170.9500
O2—H20.8400C18—C191.406 (18)
C1—C21.381 (17)C18—C211.496 (19)
C1—C61.411 (18)C19—C201.378 (19)
C2—C31.405 (18)C19—H190.9500
C2—H2a0.9500C20—H200.9500
C3—C41.368 (19)C21—H21A0.9800
C3—H30.9500C21—H21B0.9800
C4—C51.404 (17)C21—H21C0.9800
C4—C71.507 (19)C22—C271.391 (18)
C5—C61.380 (18)C22—C231.400 (16)
C5—H50.9500C23—C241.390 (19)
C6—H60.9500C23—H230.9500
C7—H7A0.9800C24—C251.357 (19)
C7—H7B0.9800C24—H240.9500
C7—H7C0.9800C25—C261.383 (19)
C8—C131.374 (18)C25—C281.525 (19)
C8—C91.403 (19)C26—C271.37 (2)
C9—C101.383 (18)C26—H260.9500
C9—H90.9500C27—H270.9500
C10—C111.384 (18)C28—H28A0.9800
C10—H100.9500C28—H28B0.9800
C11—C121.37 (2)C28—H28C0.9800
O1—Sn1—C8119.8 (4)C10—C11—C14121.3 (14)
O1—Sn1—C1112.0 (4)C11—C12—C13120.8 (13)
C8—Sn1—C1126.5 (5)C11—C12—H12119.6
O1—Sn1—O1i69.1 (3)C13—C12—H12119.6
C8—Sn1—O1i94.3 (4)C8—C13—C12121.1 (15)
C1—Sn1—O1i91.6 (4)C8—C13—H13119.5
O1—Sn1—Br190.9 (2)C12—C13—H13119.5
C8—Sn1—Br195.4 (3)C11—C14—H14A109.5
C1—Sn1—Br196.5 (3)C11—C14—H14B109.5
O1i—Sn1—Br1160.0 (2)H14A—C14—H14B109.5
O2—Sn2—C22118.3 (4)C11—C14—H14C109.5
O2—Sn2—C15114.3 (4)H14A—C14—H14C109.5
C22—Sn2—C15126.0 (5)H14B—C14—H14C109.5
O2—Sn2—O2ii69.2 (4)C20—C15—C16119.0 (12)
C22—Sn2—O2ii93.8 (4)C20—C15—Sn2120.5 (9)
C15—Sn2—O2ii93.7 (4)C16—C15—Sn2120.3 (10)
O2—Sn2—Br287.4 (2)C15—C16—C17119.1 (12)
C22—Sn2—Br296.9 (3)C15—C16—H16120.4
C15—Sn2—Br296.7 (3)C17—C16—H16120.4
O2ii—Sn2—Br2156.6 (2)C18—C17—C16122.4 (12)
Sn1—O1—Sn1i110.9 (3)C18—C17—H17118.8
Sn1—O1—H1124.6C16—C17—H17118.8
Sn1i—O1—H1124.6C17—C18—C19117.8 (13)
Sn2—O2—Sn2ii110.8 (4)C17—C18—C21122.2 (12)
Sn2—O2—H2124.6C19—C18—C21119.9 (13)
Sn2ii—O2—H2124.6C20—C19—C18120.8 (14)
C2—C1—C6119.9 (11)C20—C19—H19119.6
C2—C1—Sn1119.4 (10)C18—C19—H19119.6
C6—C1—Sn1120.7 (9)C19—C20—C15120.8 (11)
C1—C2—C3118.2 (13)C19—C20—H20119.6
C1—C2—H2a120.9C15—C20—H20119.6
C3—C2—H2a120.9C18—C21—H21A109.5
C4—C3—C2123.6 (12)C18—C21—H21B109.5
C4—C3—H3118.2H21A—C21—H21B109.5
C2—C3—H3118.2C18—C21—H21C109.5
C3—C4—C5116.9 (13)H21A—C21—H21C109.5
C3—C4—C7123.0 (12)H21B—C21—H21C109.5
C5—C4—C7120.0 (13)C27—C22—C23118.1 (12)
C6—C5—C4121.7 (13)C27—C22—Sn2120.1 (9)
C6—C5—H5119.2C23—C22—Sn2120.8 (10)
C4—C5—H5119.2C24—C23—C22118.5 (12)
C5—C6—C1119.7 (11)C24—C23—H23120.8
C5—C6—H6120.2C22—C23—H23120.8
C1—C6—H6120.2C25—C24—C23122.6 (12)
C4—C7—H7A109.5C25—C24—H24118.7
C4—C7—H7B109.5C23—C24—H24118.7
H7A—C7—H7B109.5C24—C25—C26119.2 (13)
C4—C7—H7C109.5C24—C25—C28120.9 (12)
H7A—C7—H7C109.5C26—C25—C28119.8 (13)
H7B—C7—H7C109.5C27—C26—C25119.3 (13)
C13—C8—C9117.9 (12)C27—C26—H26120.4
C13—C8—Sn1119.5 (11)C25—C26—H26120.4
C9—C8—Sn1122.6 (9)C26—C27—C22122.2 (12)
C10—C9—C8120.9 (12)C26—C27—H27118.9
C10—C9—H9119.5C22—C27—H27118.9
C8—C9—H9119.5C25—C28—H28A109.5
C11—C10—C9120.3 (14)C25—C28—H28B109.5
C11—C10—H10119.8H28A—C28—H28B109.5
C9—C10—H10119.8C25—C28—H28C109.5
C12—C11—C10119.0 (12)H28A—C28—H28C109.5
C12—C11—C14119.6 (12)H28B—C28—H28C109.5
C8—Sn1—O1—Sn1i−82.8 (5)C14—C11—C12—C13178.7 (13)
C1—Sn1—O1—Sn1i83.0 (5)C9—C8—C13—C120(2)
O1i—Sn1—O1—Sn1i0.0Sn1—C8—C13—C12−177.5 (11)
Br1—Sn1—O1—Sn1i−179.6 (3)C11—C12—C13—C82(2)
C22—Sn2—O2—Sn2ii−82.9 (6)O2—Sn2—C15—C20−74.5 (10)
C15—Sn2—O2—Sn2ii84.5 (5)C22—Sn2—C15—C2091.8 (11)
O2ii—Sn2—O2—Sn2ii0.0O2ii—Sn2—C15—C20−5.6 (10)
Br2—Sn2—O2—Sn2ii−179.4 (3)Br2—Sn2—C15—C20−164.6 (10)
O1—Sn1—C1—C2−127.0 (9)O2—Sn2—C15—C16111.9 (10)
C8—Sn1—C1—C237.7 (12)C22—Sn2—C15—C16−81.8 (11)
O1i—Sn1—C1—C2−58.9 (10)O2ii—Sn2—C15—C16−179.3 (9)
Br1—Sn1—C1—C2139.4 (9)Br2—Sn2—C15—C1621.8 (10)
O1—Sn1—C1—C654.4 (11)C20—C15—C16—C171.4 (18)
C8—Sn1—C1—C6−140.9 (9)Sn2—C15—C16—C17175.2 (9)
O1i—Sn1—C1—C6122.5 (10)C15—C16—C17—C180.3 (19)
Br1—Sn1—C1—C6−39.3 (10)C16—C17—C18—C19−1.4 (19)
C6—C1—C2—C3−0.4 (18)C16—C17—C18—C21−179.3 (12)
Sn1—C1—C2—C3−179.0 (9)C17—C18—C19—C201(2)
C1—C2—C3—C4−1.6 (19)C21—C18—C19—C20178.7 (13)
C2—C3—C4—C52.0 (19)C18—C19—C20—C151(2)
C2—C3—C4—C7−175.1 (12)C16—C15—C20—C19−2.0 (19)
C3—C4—C5—C6−0.4 (19)Sn2—C15—C20—C19−175.8 (10)
C7—C4—C5—C6176.8 (11)O2—Sn2—C22—C27−116.7 (10)
C4—C5—C6—C1−1.4 (18)C15—Sn2—C22—C2777.5 (12)
C2—C1—C6—C51.8 (18)O2ii—Sn2—C22—C27174.9 (10)
Sn1—C1—C6—C5−179.6 (9)Br2—Sn2—C22—C27−25.9 (10)
O1—Sn1—C8—C13−123.0 (10)O2—Sn2—C22—C2375.3 (11)
C1—Sn1—C8—C1373.4 (12)C15—Sn2—C22—C23−90.5 (11)
O1i—Sn1—C8—C13168.7 (10)O2ii—Sn2—C22—C236.9 (10)
Br1—Sn1—C8—C13−28.8 (11)Br2—Sn2—C22—C23166.0 (10)
O1—Sn1—C8—C959.6 (11)C27—C22—C23—C243.0 (19)
C1—Sn1—C8—C9−104.0 (11)Sn2—C22—C23—C24171.3 (10)
O1i—Sn1—C8—C9−8.8 (10)C22—C23—C24—C25−4(2)
Br1—Sn1—C8—C9153.7 (10)C23—C24—C25—C263(2)
C13—C8—C9—C10−1.3 (19)C23—C24—C25—C28−175.5 (13)
Sn1—C8—C9—C10176.3 (10)C24—C25—C26—C27−1(2)
C8—C9—C10—C110(2)C28—C25—C26—C27177.6 (13)
C9—C10—C11—C122(2)C25—C26—C27—C220(2)
C9—C10—C11—C14−179.9 (12)C23—C22—C27—C26−1(2)
C10—C11—C12—C13−3(2)Sn2—C22—C27—C26−169.4 (11)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···Br1i0.842.493.329 (8)173
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···Br1i0.842.493.329 (8)173
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

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

references
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