catena-Poly[[cyclo­hexyl­diphenyl­tin(IV)]-μ-hydroxido-κ2O:O]

Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536808011100

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages m724-m725

doi:10.1107/S1600536808011100

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catena-Poly[[cyclohexyldiphenyltin(IV)]-μ-hydroxido-κ²O:O]

Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 26 March 2008; accepted 20 April 2008; online 26 April 2008)

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.

Related literature

For background literature on mixed alkyl/diaryltin(IV) 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

Crystal data

[Sn(C₆H₅)₂(C₆H₁₁)(OH)]
M_r = 373.05
Orthorhombic, C m c 2₁
a = 18.3830 (2) Å
b = 10.2801 (1) Å
c = 8.1762 (1) Å
V = 1545.13 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.65 mm⁻¹
T = 100 (2) K
0.22 × 0.09 × 0.08 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.771, T_max = 0.880
9651 measured reflections
1711 independent reflections
1637 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.017
wR(F²) = 0.071
S = 1.28
1711 reflections
97 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.31 e Å⁻³
Absolute structure: Flack (1983 ), 650 Friedel pairs
Flack parameter: 0.02 (4)

Table 1
Selected geometric parameters (Å, °)

Sn1—O1	2.201 (4)
Sn1—C1	2.159 (4)
Sn1—C5	2.139 (3)

C1—Sn1—C5	118.4 (1)
C1—Sn1—O1	94.1 (2)
C1—Sn1—O1ⁱ	89.8 (2)
C5—Sn1—C5ⁱⁱ	122.9 (2)
C5—Sn1—O1	90.7 (1)
C5—Sn1—O1ⁱ	87.5 (1)
O1—Sn1—O1ⁱ	176.1 (1)
Sn1—O1—Sn1ⁱⁱⁱ	133.7 (2)
Symmetry codes: (i) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (ii) -x+1, y, z; (iii) $[-x+1, -y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011100/tk2257sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011100/tk2257Isup2.hkl

checkCIF report

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.

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

	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.
	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)]	F(000) = 752
M_r = 373.05	D_x = 1.604 Mg m⁻³
Orthorhombic, Cmc2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c -2	Cell parameters from 8850 reflections
a = 18.3830 (2) Å	θ = 2.2–28.3°
b = 10.2801 (1) Å	µ = 1.65 mm⁻¹
c = 8.1762 (1) Å	T = 100 K
V = 1545.13 (3) Å³	Prism, colorless
Z = 4	0.22 × 0.09 × 0.08 mm

Data collection top

Bruker SMART APEXII diffractometer	1711 independent reflections
Radiation source: fine-focus sealed tube	1637 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
T_min = 0.771, T_max = 0.880	k = −13→13
9651 measured reflections	l = −9→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.017	H-atom parameters constrained
wR(F²) = 0.071	w = 1/[σ²(F_o²) + (0.0421P)² + 0.0692P] where P = (F_o² + 2F_c²)/3
S = 1.28	(Δ/σ)_max = 0.001
1711 reflections	Δρ_max = 0.57 e Å⁻³
97 parameters	Δρ_min = −0.31 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 650 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (4)

Crystal data top

[Sn(C₆H₅)₂(C₆H₁₁)(OH)]	V = 1545.13 (3) Å³
M_r = 373.05	Z = 4
Orthorhombic, Cmc2₁	Mo Kα radiation
a = 18.3830 (2) Å	µ = 1.65 mm⁻¹
b = 10.2801 (1) Å	T = 100 K
c = 8.1762 (1) Å	0.22 × 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)
T_min = 0.771, T_max = 0.880	R_int = 0.024
9651 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.017	H-atom parameters constrained
wR(F²) = 0.071	Δρ_max = 0.57 e Å⁻³
S = 1.28	Δρ_min = −0.31 e Å⁻³
1711 reflections	Absolute structure: Flack (1983), 650 Friedel pairs
97 parameters	Absolute structure parameter: 0.02 (4)
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Sn1	0.5000	0.494121 (18)	0.50000 (18)	0.01298 (10)
O1	0.5000	0.5850 (3)	0.2563 (4)	0.0165 (6)
H1O	0.5000	0.6666	0.2598	0.025*
C1	0.5000	0.2980 (4)	0.4053 (6)	0.0189 (9)
H1	0.5000	0.3071	0.2836	0.023*
C2	0.43184 (16)	0.2226 (3)	0.4465 (5)	0.0234 (7)
H2A	0.3888	0.2721	0.4084	0.028*
H2B	0.4281	0.2132	0.5667	0.028*
C3	0.4313 (2)	0.0883 (3)	0.3681 (5)	0.0260 (8)
H3A	0.3885	0.0392	0.4078	0.031*
H3B	0.4268	0.0977	0.2480	0.031*
C4	0.5000	0.0125 (4)	0.4074 (8)	0.0248 (13)
H4A	0.5000	−0.0102	0.5251	0.030*
H4B	0.5000	−0.0696	0.3442	0.030*
C5	0.60222 (16)	0.5831 (3)	0.5558 (4)	0.0170 (6)
C6	0.62261 (15)	0.7060 (2)	0.5004 (5)	0.0227 (6)
H6	0.5897	0.7548	0.4352	0.027*
C7	0.69028 (19)	0.7587 (3)	0.5387 (4)	0.0296 (8)
H7	0.7023	0.8441	0.5036	0.036*
C8	0.74004 (18)	0.6867 (4)	0.6280 (5)	0.0308 (8)
H8	0.7867	0.7216	0.6514	0.037*
C9	0.72163 (17)	0.5644 (4)	0.6826 (5)	0.0256 (7)
H9	0.7553	0.5149	0.7449	0.031*
C10	0.6529 (3)	0.5133 (3)	0.6458 (7)	0.0247 (9)
H10	0.6407	0.4287	0.6836	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01281 (14)	0.01401 (14)	0.01211 (16)	0.000	0.000	0.0003 (2)
O1	0.0227 (14)	0.0168 (15)	0.0101 (15)	0.000	0.000	−0.0008 (11)
C1	0.022 (2)	0.0167 (19)	0.018 (2)	0.000	0.000	0.0005 (17)
C2	0.0200 (15)	0.0215 (14)	0.0288 (19)	−0.0023 (11)	0.0003 (13)	−0.0006 (12)
C3	0.0306 (19)	0.0193 (15)	0.028 (2)	−0.0044 (13)	0.0033 (14)	0.0001 (14)
C4	0.038 (4)	0.019 (2)	0.017 (3)	0.000	0.000	−0.0032 (17)
C5	0.0168 (13)	0.0194 (13)	0.0147 (15)	−0.0006 (12)	0.0029 (11)	−0.0018 (11)
C6	0.0268 (14)	0.0242 (12)	0.0171 (16)	−0.0042 (10)	−0.0025 (17)	0.001 (2)
C7	0.0366 (18)	0.0302 (16)	0.022 (2)	−0.0150 (14)	0.0004 (14)	0.0036 (13)
C8	0.0213 (16)	0.043 (2)	0.028 (2)	−0.0107 (14)	−0.0009 (15)	−0.0088 (16)
C9	0.0174 (15)	0.0343 (19)	0.0250 (18)	0.0007 (13)	−0.0047 (13)	−0.0072 (15)
C10	0.023 (2)	0.0195 (17)	0.032 (3)	−0.0007 (11)	−0.0051 (18)	−0.0014 (14)

Geometric parameters (Å, º) top

Sn1—O1	2.201 (4)	C8—C9	1.377 (5)
Sn1—C1	2.159 (4)	C9—C10	1.400 (5)
Sn1—C5	2.139 (3)	O1—H1O	0.8400
Sn1—C5ⁱ	2.139 (3)	C1—H1	1.0000
Sn1—O1ⁱⁱ	2.248 (4)	C2—H2A	0.9900
O1—Sn1ⁱⁱⁱ	2.248 (4)	C2—H2B	0.9900
C1—C2	1.511 (4)	C3—H3A	0.9900
C1—C2ⁱ	1.511 (4)	C3—H3B	0.9900
C2—C3	1.522 (4)	C4—H4A	0.9900
C3—C4	1.518 (4)	C4—H4B	0.9900
C4—C3ⁱ	1.518 (4)	C6—H6	0.9500
C5—C10	1.388 (6)	C7—H7	0.9500
C5—C6	1.394 (4)	C8—H8	0.9500
C6—C7	1.393 (4)	C9—H9	0.9500
C7—C8	1.385 (5)	C10—H10	0.9500

C1—Sn1—C5	118.4 (1)	C2—C1—H1	105.6
C1—Sn1—O1	94.1 (2)	Sn1—C1—H1	105.6
C1—Sn1—O1ⁱⁱ	89.8 (2)	C1—C2—H2A	109.2
C5—Sn1—C5ⁱ	122.9 (2)	C3—C2—H2A	109.2
C5—Sn1—O1	90.7 (1)	C1—C2—H2B	109.2
C5—Sn1—O1ⁱⁱ	87.5 (1)	C3—C2—H2B	109.2
C5ⁱ—Sn1—C1	118.4 (1)	H2A—C2—H2B	107.9
C5ⁱ—Sn1—O1	90.7 (1)	C4—C3—H3A	109.3
C5ⁱ—Sn1—O1ⁱⁱ	87.5 (1)	C2—C3—H3A	109.3
O1—Sn1—O1ⁱⁱ	176.1 (1)	C4—C3—H3B	109.3
Sn1—O1—Sn1ⁱⁱⁱ	133.7 (2)	C2—C3—H3B	109.3
C2—C1—C2ⁱ	112.0 (3)	H3A—C3—H3B	107.9
C2—C1—Sn1	113.5 (2)	C3ⁱ—C4—H4A	109.1
C2ⁱ—C1—Sn1	113.5 (2)	C3—C4—H4A	109.1
C1—C2—C3	112.1 (3)	C3ⁱ—C4—H4B	109.1
C4—C3—C2	111.8 (3)	C3—C4—H4B	109.1
C3ⁱ—C4—C3	112.5 (4)	H4A—C4—H4B	107.8
C10—C5—C6	117.4 (3)	C7—C6—H6	119.3
C10—C5—Sn1	118.8 (2)	C5—C6—H6	119.3
C6—C5—Sn1	123.7 (2)	C8—C7—H7	120.0
C7—C6—C5	121.3 (3)	C6—C7—H7	120.0
C8—C7—C6	120.0 (3)	C9—C8—H8	120.1
C9—C8—C7	119.8 (3)	C7—C8—H8	120.1
C8—C9—C10	119.6 (4)	C8—C9—H9	120.2
C5—C10—C9	121.7 (3)	C10—C9—H9	120.2
Sn1—O1—H1O	113.2	C5—C10—H10	119.1
Sn1ⁱⁱⁱ—O1—H1O	113.2	C9—C10—H10	119.1

C5—Sn1—O1—Sn1ⁱⁱⁱ	118.53 (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—Sn1ⁱⁱⁱ	0.0	O1ⁱⁱ—Sn1—C5—C10	41.0 (3)
C5—Sn1—C1—C2	151.7 (2)	C5ⁱ—Sn1—C5—C6	−56.7 (4)
C5ⁱ—Sn1—C1—C2	−22.3 (3)	C1—Sn1—C5—C6	129.6 (3)
O1—Sn1—C1—C2	−115.3 (3)	O1—Sn1—C5—C6	34.5 (3)
O1ⁱⁱ—Sn1—C1—C2	64.7 (3)	O1ⁱⁱ—Sn1—C5—C6	−142.0 (3)
C5—Sn1—C1—C2ⁱ	22.3 (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—C2ⁱ	115.3 (3)	C5—C6—C7—C8	2.6 (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—C10	0.7 (6)
Sn1—C1—C2—C3	176.0 (3)	C6—C5—C10—C9	1.0 (6)
C1—C2—C3—C4	52.9 (5)	Sn1—C5—C10—C9	178.2 (3)
C2—C3—C4—C3ⁱ	−52.3 (6)	C8—C9—C10—C5	−0.3 (7)
C5ⁱ—Sn1—C5—C10	126.3 (3)

Symmetry codes: (i) −x+1, y, z; (ii) −x+1, −y+1, z+1/2; (iii) −x+1, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₂(C₆H₁₁)(OH)]
M_r	373.05
Crystal system, space group	Orthorhombic, Cmc2₁
Temperature (K)	100
a, b, c (Å)	18.3830 (2), 10.2801 (1), 8.1762 (1)
V (Å³)	1545.13 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.65
Crystal size (mm)	0.22 × 0.09 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.771, 0.880
No. of measured, independent and observed [I > 2σ(I)] reflections	9651, 1711, 1637
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.017, 0.071, 1.28
No. of reflections	1711
No. of parameters	97
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.31
Absolute structure	Flack (1983), 650 Friedel pairs
Absolute structure parameter	0.02 (4)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Selected geometric parameters (Å, º) top

Sn1—O1	2.201 (4)	Sn1—C5	2.139 (3)
Sn1—C1	2.159 (4)

C1—Sn1—C5	118.4 (1)	C5—Sn1—O1	90.7 (1)
C1—Sn1—O1	94.1 (2)	C5—Sn1—O1ⁱ	87.5 (1)
C1—Sn1—O1ⁱ	89.8 (2)	O1—Sn1—O1ⁱ	176.1 (1)
C5—Sn1—C5ⁱⁱ	122.9 (2)	Sn1—O1—Sn1ⁱⁱⁱ	133.7 (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

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

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