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Acta Cryst. (2008). E64, m724-m725    [ doi:10.1107/S1600536808011100 ]

catena-Poly[[cyclohexyldiphenyltin(IV)]-[mu]-hydroxido-[kappa]2O:O]

K. M. Lo and S. W. Ng

Abstract top

The title polymeric mixed-organyl tin hydroxide, [Sn(C6H5)2(C6H11)(OH)]n, hass a hydroxide-bridged chain structure; the tin center shows trans-C3SnO2 trigonal bipyramidal coordination. The Sn atom lies on a special position of site symmetry m; the symmetry element relates one phenyl ring to the other and also relates one half of the cyclohexyl ring to the other half.

Comment top

Mixed alkyl/diaryltin compounds possess much more useful activity against plant pathogens than the symmetrical triorganotin homologs, particularly if one of the alkyl substituent is a cyclic unit (Koshy et al., 2001). The title compound (I) is the starting reactant for the synthesis of mixed organotin carboxylates.

The compound adopts a zigzag chain motif that propagates along the c-axis of the orthorhombic unit cell; the tin center shows trans-C3SnO2 trigonal bipyramidal coordination (Figs 1 and 2 & Table 1).

Related literature top

For background literature on mixed alkyl/diarytin compounds, see: Koshy et al. (2001). For the synthesis of cyclohexyldiphenyltin hydroxide, see: Teo et al. (2007). For the structure of triethyltin hydroxide, see: Deacon et al. (1993). For the structure of tribenzyltin hydroxide, see: Chen et al. (2005); Reuter (2004). For the structure of triphenyltin hydroxide, see: Fu et al. (2003); Glidewell & Liles (1978); Glidewell et al. (2002). For the structure of the mixed organyl compound, benzyldimethyltin hydroxide, see: Wannagat et al. (1993).

Experimental top

The compound was synthesized as described previously (Teo et al., 2007). Crystals were obtained by recrystallization from ethanol.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C). The hydroxo H atom (O–H 0.84 Å) was similarly treated.

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, 2008).

Figures top
[Figure 1] Fig. 1. 70% Probability thermal ellipsoid plot of the asymmetric unit in Sn(C6H11)(C6H5)2(OH) (I) extended to show the trans-C3SnO2 trigonal bipyramidal coordination geometry. Hydrogen atoms are drawn as spheres of arbitrary radius; symmetry-related atoms are not labeled.
[Figure 2] Fig. 2. Hydroxo-bridged chain motif in (I).
catena-Poly[[cyclohexyldiphenyltin(IV)]-µ-hydroxido- κ2O:O] top
Crystal data top
[Sn(C6H5)2(C6H11)(OH)]F000 = 752
Mr = 373.05Dx = 1.604 Mg m−3
Orthorhombic, Cmc21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: C 2c -2Cell parameters from 8850 reflections
a = 18.3830 (2) Åθ = 2.2–28.3º
b = 10.2801 (1) ŵ = 1.65 mm−1
c = 8.1762 (1) ÅT = 100 (2) K
V = 1545.13 (3) Å3Prism, colorless
Z = 40.22 × 0.09 × 0.08 mm
Data collection top
Bruker SMART APEXII
diffractometer		1711 independent reflections
Radiation source: fine-focus sealed tube1637 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.024
T = 100(2) Kθmax = 27.5º
ω scansθmin = 2.2º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −23→23
Tmin = 0.771, Tmax = 0.880k = −13→13
9651 measured reflectionsl = −9→10
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.017  w = 1/[σ2(Fo2) + (0.0421P)2 + 0.0692P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.071(Δ/σ)max = 0.001
S = 1.28Δρmax = 0.57 e Å−3
1711 reflectionsΔρmin = −0.31 e Å−3
97 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 650 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (4)
Secondary atom site location: difference Fourier map
Crystal data top
[Sn(C6H5)2(C6H11)(OH)]V = 1545.13 (3) Å3
Mr = 373.05Z = 4
Orthorhombic, Cmc21Mo Kα
a = 18.3830 (2) ŵ = 1.65 mm−1
b = 10.2801 (1) ÅT = 100 (2) K
c = 8.1762 (1) Å0.22 × 0.09 × 0.08 mm
Data collection top
Bruker SMART APEXII
diffractometer		1711 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1637 reflections with I > 2σ(I)
Tmin = 0.771, Tmax = 0.880Rint = 0.024
9651 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.017H-atom parameters constrained
wR(F2) = 0.071Δρmax = 0.57 e Å−3
S = 1.28Δρmin = −0.31 e Å−3
1711 reflectionsAbsolute structure: Flack (1983), 650 Friedel pairs
97 parametersFlack parameter: 0.02 (4)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.50000.494121 (18)0.50000 (18)0.01298 (10)
O10.50000.5850 (3)0.2563 (4)0.0165 (6)
H1O0.50000.66660.25980.025*
C10.50000.2980 (4)0.4053 (6)0.0189 (9)
H10.50000.30710.28360.023*
C20.43184 (16)0.2226 (3)0.4465 (5)0.0234 (7)
H2A0.38880.27210.40840.028*
H2B0.42810.21320.56670.028*
C30.4313 (2)0.0883 (3)0.3681 (5)0.0260 (8)
H3A0.38850.03920.40780.031*
H3B0.42680.09770.24800.031*
C40.50000.0125 (4)0.4074 (8)0.0248 (13)
H4A0.5000−0.01020.52510.030*
H4B0.5000−0.06960.34420.030*
C50.60222 (16)0.5831 (3)0.5558 (4)0.0170 (6)
C60.62261 (15)0.7060 (2)0.5004 (5)0.0227 (6)
H60.58970.75480.43520.027*
C70.69028 (19)0.7587 (3)0.5387 (4)0.0296 (8)
H70.70230.84410.50360.036*
C80.74004 (18)0.6867 (4)0.6280 (5)0.0308 (8)
H80.78670.72160.65140.037*
C90.72163 (17)0.5644 (4)0.6826 (5)0.0256 (7)
H90.75530.51490.74490.031*
C100.6529 (3)0.5133 (3)0.6458 (7)0.0247 (9)
H100.64070.42870.68360.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01281 (14)0.01401 (14)0.01211 (16)0.0000.0000.0003 (2)
O10.0227 (14)0.0168 (15)0.0101 (15)0.0000.000−0.0008 (11)
C10.022 (2)0.0167 (19)0.018 (2)0.0000.0000.0005 (17)
C20.0200 (15)0.0215 (14)0.0288 (19)−0.0023 (11)0.0003 (13)−0.0006 (12)
C30.0306 (19)0.0193 (15)0.028 (2)−0.0044 (13)0.0033 (14)0.0001 (14)
C40.038 (4)0.019 (2)0.017 (3)0.0000.000−0.0032 (17)
C50.0168 (13)0.0194 (13)0.0147 (15)−0.0006 (12)0.0029 (11)−0.0018 (11)
C60.0268 (14)0.0242 (12)0.0171 (16)−0.0042 (10)−0.0025 (17)0.001 (2)
C70.0366 (18)0.0302 (16)0.022 (2)−0.0150 (14)0.0004 (14)0.0036 (13)
C80.0213 (16)0.043 (2)0.028 (2)−0.0107 (14)−0.0009 (15)−0.0088 (16)
C90.0174 (15)0.0343 (19)0.0250 (18)0.0007 (13)−0.0047 (13)−0.0072 (15)
C100.023 (2)0.0195 (17)0.032 (3)−0.0007 (11)−0.0051 (18)−0.0014 (14)
Geometric parameters (Å, °) top
Sn1—O12.201 (4)C8—C91.377 (5)
Sn1—C12.159 (4)C9—C101.400 (5)
Sn1—C52.139 (3)O1—H1O0.8400
Sn1—C5i2.139 (3)C1—H11.0000
Sn1—O1ii2.248 (4)C2—H2A0.9900
O1—Sn1iii2.248 (4)C2—H2B0.9900
C1—C21.511 (4)C3—H3A0.9900
C1—C2i1.511 (4)C3—H3B0.9900
C2—C31.522 (4)C4—H4A0.9900
C3—C41.518 (4)C4—H4B0.9900
C4—C3i1.518 (4)C6—H60.9500
C5—C101.388 (6)C7—H70.9500
C5—C61.394 (4)C8—H80.9500
C6—C71.393 (4)C9—H90.9500
C7—C81.385 (5)C10—H100.9500
C1—Sn1—C5118.4 (1)C2—C1—H1105.6
C1—Sn1—O194.1 (2)Sn1—C1—H1105.6
C1—Sn1—O1ii89.8 (2)C1—C2—H2A109.2
C5—Sn1—C5i122.9 (2)C3—C2—H2A109.2
C5—Sn1—O190.7 (1)C1—C2—H2B109.2
C5—Sn1—O1ii87.5 (1)C3—C2—H2B109.2
C5i—Sn1—C1118.4 (1)H2A—C2—H2B107.9
C5i—Sn1—O190.7 (1)C4—C3—H3A109.3
C5i—Sn1—O1ii87.5 (1)C2—C3—H3A109.3
O1—Sn1—O1ii176.1 (1)C4—C3—H3B109.3
Sn1—O1—Sn1iii133.7 (2)C2—C3—H3B109.3
C2—C1—C2i112.0 (3)H3A—C3—H3B107.9
C2—C1—Sn1113.5 (2)C3i—C4—H4A109.1
C2i—C1—Sn1113.5 (2)C3—C4—H4A109.1
C1—C2—C3112.1 (3)C3i—C4—H4B109.1
C4—C3—C2111.8 (3)C3—C4—H4B109.1
C3i—C4—C3112.5 (4)H4A—C4—H4B107.8
C10—C5—C6117.4 (3)C7—C6—H6119.3
C10—C5—Sn1118.8 (2)C5—C6—H6119.3
C6—C5—Sn1123.7 (2)C8—C7—H7120.0
C7—C6—C5121.3 (3)C6—C7—H7120.0
C8—C7—C6120.0 (3)C9—C8—H8120.1
C9—C8—C7119.8 (3)C7—C8—H8120.1
C8—C9—C10119.6 (4)C8—C9—H9120.2
C5—C10—C9121.7 (3)C10—C9—H9120.2
Sn1—O1—H1O113.2C5—C10—H10119.1
Sn1iii—O1—H1O113.2C9—C10—H10119.1
C5—Sn1—O1—Sn1iii118.53 (8)C1—Sn1—C5—C10−47.4 (4)
C5i—Sn1—O1—Sn1iii−118.53 (8)O1—Sn1—C5—C10−142.4 (3)
C1—Sn1—O1—Sn1iii0.0O1ii—Sn1—C5—C1041.0 (3)
C5—Sn1—C1—C2151.7 (2)C5i—Sn1—C5—C6−56.7 (4)
C5i—Sn1—C1—C2−22.3 (3)C1—Sn1—C5—C6129.6 (3)
O1—Sn1—C1—C2−115.3 (3)O1—Sn1—C5—C634.5 (3)
O1ii—Sn1—C1—C264.7 (3)O1ii—Sn1—C5—C6−142.0 (3)
C5—Sn1—C1—C2i22.3 (3)C10—C5—C6—C7−2.2 (5)
C5i—Sn1—C1—C2i−151.7 (2)Sn1—C5—C6—C7−179.2 (3)
O1—Sn1—C1—C2i115.3 (3)C5—C6—C7—C82.6 (5)
O1ii—Sn1—C1—C2i−64.7 (3)C6—C7—C8—C9−1.8 (6)
C2i—C1—C2—C3−53.8 (5)C7—C8—C9—C100.7 (6)
Sn1—C1—C2—C3176.0 (3)C6—C5—C10—C91.0 (6)
C1—C2—C3—C452.9 (5)Sn1—C5—C10—C9178.2 (3)
C2—C3—C4—C3i−52.3 (6)C8—C9—C10—C5−0.3 (7)
C5i—Sn1—C5—C10126.3 (3)
Symmetry codes: (i) −x+1, y, z; (ii) −x+1, −y+1, z+1/2; (iii) −x+1, −y+1, z−1/2.
Table 1
Selected geometric parameters (Å, °) top
Sn1—O12.201 (4)Sn1—C52.139 (3)
Sn1—C12.159 (4)
C1—Sn1—C5118.4 (1)C5—Sn1—O190.7 (1)
C1—Sn1—O194.1 (2)C5—Sn1—O1i87.5 (1)
C1—Sn1—O1i89.8 (2)O1—Sn1—O1i176.1 (1)
C5—Sn1—C5ii122.9 (2)Sn1—O1—Sn1iii133.7 (2)
Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) −x+1, y, z; (iii) −x+1, −y+1, z−1/2.
Acknowledgements top

We thank the University of Malaya for funding this study (SF022155/2007 A) and also for the purchase of the diffractometer.

references
References top

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