catena-Poly[[cyclo-hexyl-diphenyl-tin(IV)]-μ-hydroxido-κO:O].

The title polymeric mixed-organyl tin hydroxide, [Sn(C(6)H(5))(2)(C(6)H(11))(OH)](n), hass a hydroxide-bridged chain structure; the tin center shows trans-C(3)SnO(2) 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 cyclo-hexyl 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 = 373.05

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.017

wR(F 2) = 0.071

S = 1.28

1711 reflections

97 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.31 e Å−3

Absolute structure: Flack (1983 ▶), 650 Friedel pairs

Flack parameter: 0.02 (4)

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Sn(C6H5)2(C6H11)(OH)]	F000 = 752
Mr = 373.05	Dx = 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 = 2.2–28.3º
b = 10.2801 (1) Å	µ = 1.65 mm−1
c = 8.1762 (1) Å	T = 100 (2) K
V = 1545.13 (3) Å3	Prism, colorless
Z = 4	0.22 × 0.09 × 0.08 mm

Bruker SMART APEXII diffractometer	1711 independent reflections
Radiation source: fine-focus sealed tube	1637 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
T = 100(2) K	θmax = 27.5º
ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −23→23
Tmin = 0.771, Tmax = 0.880	k = −13→13
9651 measured reflections	l = −9→10

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-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 = 1.28	Δρmax = 0.57 e Å−3
1711 reflections	Δρmin = −0.31 e Å−3
97 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 650 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (4)
Secondary atom site location: difference Fourier map

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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) ; (ii) ; (iii) .