Dichloridoocta­kis(4-chloro­benz­yl)di-μ2-hydroxido-di-μ3-oxido-tetra­tin(IV) toluene solvate

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

doi:10.1107/S1600536809015128

metal-organic compounds

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Volume 65| Part 5| May 2009| Page m593

doi:10.1107/S1600536809015128

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Dichloridooctakis(4-chlorobenzyl)di-μ₂-hydroxido-di-μ₃-oxido-tetratin(IV) toluene solvate

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 21 April 2009; accepted 23 April 2009; online 30 April 2009)

The title stannoxane is a toluene-solvated dimer, [Sn₄(C₇H₆Cl)₈Cl₂O₂(OH)₂]·C₇H₈, the tetranuclear molecule lying across a center of inversion. The Sn₄O₄ framework, whose two independent Sn atoms show trigonal bipyramidal coordination, is essentially planar (r.m.s deviation = 0.02 Å). One of the two chlorobenzyl groups of the chloridodiorganyltin unit is disordered over two positions with the chlorophenyl residue refined over two positions in a 50:50 ratio. The solvent molecule is disordered about a twofold axis.

Related literature

The distannoxane is a hydrolysed product of di(4-chlorobenzyl)dichloridotin(IV); for the synthesis of the organotin compound by the direct reaction of 4-chlorobenzyl chloride and metallic tin, see: Shishido et al. (1961 ). For octabenzyldichloridodi-μ₂-hydroxo-di-μ₃-oxo-tetratin, which crystallizes as a toluene disolvate, see: Mohamed et al. (2004 ). For octa(4-methylbenzyl)dichloridodi-μ₂-hydroxo-di-μ₃-oxo-tetratin, see: Wang et al. (2007 ).

Experimental

Crystal data

[Sn₄(C₇H₆Cl)₈Cl₂O₂(OH)₂]·C₇H₈
M_r = 1708.35
Monoclinic, C 2/c
a = 26.6531 (3) Å
b = 10.8342 (1) Å
c = 25.8025 (3) Å
β = 121.546 (1)°
V = 6349.8 (1) Å³
Z = 4
Mo Kα radiation
μ = 2.02 mm⁻¹
T = 100 K
0.36 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.564, T_max = 0.746 (expected range = 0.643–0.851)
21584 measured reflections
7288 independent reflections
6556 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.118
S = 0.97
7288 reflections
389 parameters
127 restraints
H-atom parameters constrained
Δρ_max = 1.08 e Å⁻³
Δρ_min = −1.53 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015128/tk2437sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015128/tk2437Isup2.hkl

checkCIF report

Related literature top

The distannoxane is a hydrolysed product of di(4-chlorobenzyl)dichloridotin(IV); for the synthesis of the organotin compound by the direct reaction of 4-chlorobenzyl chloride and metallic tin, see: Shishido et al. (1961). For octabenzyldichloridodi-µ₂-hydroxo-di-µ₃-oxo-tetratin, which crystallizes as a toluene disolvate, see: Mohamed et al. (2004). For octa(4-methylbenzyl)dichloridodi-µ₂-hydroxo-di-µ₃-oxo-tetratin, see: Wang et al. (2007).

Experimental top

Di(4-chlorobenzyl)tin dichloride (1 g, 2.2 mmol) (Shishido et al., 1961) was recrystallized from toluene in the presence of excess pyridine (1 ml) to give well formed, colorless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [Sn₂Cl(C₇H₆Cl)₄O(OH)]₂^.C₇H₈ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. For reasons of clarity, the disorder in the chlorophenyl group is not shown nor is the disordered solvent molecule. Unlabelled atoms are related to the labelled atoms by a centre of inversion.

Dichloridooctakis(4-chlorobenzyl)di-µ₂-hydroxido-di-µ₃-oxido-tetratin(IV) toluene solvate top

Crystal data top

[Sn₄(C₇H₆Cl)₈Cl₂O₂(OH)₂]·C₇H₈	F(000) = 3352
M_r = 1708.35	D_x = 1.787 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9991 reflections
a = 26.6531 (3) Å	θ = 2.5–28.3°
b = 10.8342 (1) Å	µ = 2.02 mm⁻¹
c = 25.8025 (3) Å	T = 100 K
β = 121.546 (1)°	Block, colorless
V = 6349.8 (1) Å³	0.36 × 0.12 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	7288 independent reflections
Radiation source: fine-focus sealed tube	6556 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −34→34
T_min = 0.564, T_max = 0.746	k = −14→14
21584 measured reflections	l = −33→33

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
7288 reflections	(Δ/σ)_max = 0.001
389 parameters	Δρ_max = 1.08 e Å⁻³
127 restraints	Δρ_min = −1.53 e Å⁻³

Crystal data top

[Sn₄(C₇H₆Cl)₈Cl₂O₂(OH)₂]·C₇H₈	V = 6349.8 (1) Å³
M_r = 1708.35	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 26.6531 (3) Å	µ = 2.02 mm⁻¹
b = 10.8342 (1) Å	T = 100 K
c = 25.8025 (3) Å	0.36 × 0.12 × 0.08 mm
β = 121.546 (1)°

Data collection top

Bruker SMART APEX diffractometer	7288 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6556 reflections with I > 2σ(I)
T_min = 0.564, T_max = 0.746	R_int = 0.025
21584 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	127 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 0.97	Δρ_max = 1.08 e Å⁻³
7288 reflections	Δρ_min = −1.53 e Å⁻³
389 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.327847 (9)	0.98788 (2)	0.507504 (10)	0.01694 (9)
Sn2	0.275327 (9)	0.70201 (2)	0.456210 (9)	0.01484 (9)
Cl1	0.44736 (9)	1.2278 (2)	0.33532 (10)	0.0402 (5)	0.50
Cl1'	0.47812 (11)	1.3027 (2)	0.39056 (13)	0.0466 (6)	0.50
Cl2	0.56752 (4)	1.39884 (11)	0.58933 (5)	0.0421 (3)
Cl3	0.42907 (6)	0.44291 (13)	0.75877 (5)	0.0566 (4)
Cl4	0.27115 (4)	0.87250 (9)	0.18192 (4)	0.0302 (2)
Cl5	0.29674 (4)	1.10490 (8)	0.56878 (4)	0.02368 (18)
O1	0.33270 (10)	0.8384 (2)	0.45170 (10)	0.0201 (5)
H2	0.3515	0.8354	0.4338	0.030*
O2	0.27917 (10)	0.8466 (2)	0.50928 (10)	0.0167 (4)
C1	0.28989 (16)	1.1114 (4)	0.43078 (17)	0.0255 (8)
H1A	0.2541	1.0731	0.3966	0.031*	0.50
H1B	0.2780	1.1888	0.4419	0.031*	0.50
H1C	0.2582	1.0675	0.3949	0.031*	0.50
H1D	0.2719	1.1825	0.4392	0.031*	0.50
C2	0.3321 (3)	1.1416 (7)	0.4104 (3)	0.019 (3)	0.50
C3	0.3242 (2)	1.0776 (6)	0.3600 (3)	0.0192 (17)	0.50
H3	0.2944	1.0165	0.3413	0.023*	0.50
C4	0.3600 (2)	1.1032 (5)	0.3369 (2)	0.0224 (14)	0.50
H4	0.3546	1.0595	0.3024	0.027*	0.50
C5	0.4036 (2)	1.1927 (6)	0.3643 (3)	0.0240 (18)	0.50
C6	0.4115 (2)	1.2566 (5)	0.4148 (3)	0.0246 (19)	0.50
H6	0.4413	1.3178	0.4335	0.030*	0.50
C7	0.3757 (3)	1.2310 (6)	0.4378 (3)	0.0190 (18)	0.50
H7	0.3811	1.2747	0.4723	0.023*	0.50
C2'	0.3344 (3)	1.1548 (7)	0.4162 (3)	0.017 (3)	0.50
C3'	0.3450 (3)	1.0990 (6)	0.3743 (3)	0.0242 (19)	0.50
H3'	0.3220	1.0302	0.3514	0.029*	0.50
C4'	0.3891 (3)	1.1441 (6)	0.3660 (3)	0.0277 (18)	0.50
H4'	0.3964	1.1060	0.3374	0.033*	0.50
C5'	0.4227 (2)	1.2449 (6)	0.3996 (3)	0.028 (2)	0.50
C6'	0.4121 (2)	1.3006 (5)	0.4415 (3)	0.0279 (17)	0.50
H6'	0.4350	1.3695	0.4645	0.033*	0.50
C7'	0.3679 (3)	1.2556 (6)	0.4498 (3)	0.0177 (18)	0.50
H7'	0.3607	1.2936	0.4784	0.021*	0.50
C8	0.41833 (15)	0.9705 (3)	0.57839 (17)	0.0237 (7)
H8A	0.4206	0.9632	0.6178	0.028*
H8B	0.4343	0.8933	0.5720	0.028*
C9	0.45657 (9)	1.07721 (16)	0.58191 (10)	0.0195 (6)
C10	0.49762 (10)	1.06170 (16)	0.56468 (11)	0.0251 (7)
H10	0.5022	0.9833	0.5512	0.030*
C11	0.53194 (9)	1.1609 (2)	0.56725 (11)	0.0270 (8)
H11	0.5600	1.1503	0.5555	0.032*
C12	0.52521 (9)	1.27552 (18)	0.58704 (12)	0.0286 (8)
C13	0.48416 (10)	1.29103 (16)	0.60427 (11)	0.0253 (7)
H13	0.4796	1.3694	0.6178	0.030*
C14	0.44984 (9)	1.19187 (19)	0.60170 (11)	0.0219 (7)
H14	0.4218	1.2025	0.6135	0.026*
C15	0.34351 (17)	0.5660 (4)	0.49764 (18)	0.0281 (8)
H15A	0.3291	0.4888	0.4737	0.034*
H15B	0.3777	0.5950	0.4956	0.034*
C16	0.36408 (10)	0.5374 (2)	0.56319 (8)	0.0217 (7)
C17	0.40371 (11)	0.61529 (19)	0.60939 (11)	0.0465 (13)
H17	0.4170	0.6882	0.5997	0.056*
C18	0.42397 (12)	0.5865 (2)	0.66972 (10)	0.0543 (15)
H18	0.4511	0.6398	0.7013	0.065*
C19	0.40460 (11)	0.4799 (2)	0.68384 (7)	0.0331 (9)
C20	0.36497 (10)	0.40193 (18)	0.63764 (10)	0.0232 (7)
H20	0.3517	0.3290	0.6473	0.028*
C21	0.34471 (9)	0.43068 (19)	0.57732 (8)	0.0218 (7)
H21	0.3176	0.3774	0.5457	0.026*
C22	0.20707 (16)	0.7021 (4)	0.36242 (16)	0.0257 (8)
H22A	0.1921	0.6167	0.3505	0.031*
H22B	0.1742	0.7537	0.3575	0.031*
C23	0.22529 (9)	0.7490 (2)	0.31922 (9)	0.0198 (7)
C24	0.19185 (8)	0.8399 (2)	0.27705 (10)	0.0253 (7)
H24	0.1590	0.8749	0.2768	0.030*
C25	0.20642 (10)	0.8794 (2)	0.23531 (9)	0.0274 (8)
H25	0.1836	0.9415	0.2065	0.033*
C26	0.25443 (10)	0.8281 (2)	0.23573 (9)	0.0223 (7)
C27	0.28787 (9)	0.7373 (2)	0.27789 (10)	0.0259 (7)
H27	0.3207	0.7022	0.2782	0.031*
C28	0.27330 (9)	0.6977 (2)	0.31963 (9)	0.0244 (7)
H28	0.2962	0.6356	0.3484	0.029*
C29	0.4229 (5)	0.9306 (13)	0.2428 (6)	0.033 (2)	0.50
H29A	0.4038	1.0072	0.2436	0.050*	0.50
H29B	0.4315	0.8792	0.2777	0.050*	0.50
H29C	0.3967	0.8858	0.2050	0.050*	0.50
C30	0.47904 (19)	0.9607 (5)	0.2457 (3)	0.0256 (15)	0.50
C31	0.4921 (3)	1.0827 (4)	0.2406 (3)	0.032 (2)	0.50
H31	0.4652	1.1465	0.2351	0.039*	0.50
C32	0.5444 (3)	1.1115 (4)	0.2438 (3)	0.043 (2)	0.50
H32	0.5533	1.1948	0.2403	0.052*	0.50
C33	0.5837 (2)	1.0182 (6)	0.2519 (3)	0.038 (2)	0.50
H33	0.6195	1.0378	0.2541	0.046*	0.50
C34	0.5707 (2)	0.8962 (5)	0.2570 (4)	0.036 (3)	0.50
H34	0.5976	0.8324	0.2625	0.043*	0.50
C35	0.5183 (2)	0.8675 (4)	0.2538 (3)	0.0278 (16)	0.50
H35	0.5094	0.7841	0.2573	0.033*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01971 (14)	0.01661 (14)	0.01916 (14)	−0.00310 (8)	0.01341 (11)	0.00117 (8)
Sn2	0.01654 (13)	0.01655 (14)	0.01512 (13)	0.00008 (8)	0.01083 (10)	0.00288 (8)
Cl1	0.0258 (9)	0.0584 (13)	0.0445 (12)	0.0056 (9)	0.0240 (9)	0.0273 (10)
Cl1'	0.0477 (12)	0.0421 (12)	0.0787 (17)	0.0062 (9)	0.0528 (13)	0.0182 (11)
Cl2	0.0310 (5)	0.0405 (6)	0.0516 (6)	−0.0154 (4)	0.0194 (5)	0.0024 (5)
Cl3	0.0672 (8)	0.0566 (8)	0.0172 (5)	0.0364 (6)	0.0022 (5)	−0.0001 (5)
Cl4	0.0372 (5)	0.0391 (5)	0.0220 (4)	−0.0055 (4)	0.0209 (4)	0.0018 (4)
Cl5	0.0323 (4)	0.0210 (4)	0.0269 (4)	−0.0033 (3)	0.0217 (4)	−0.0027 (3)
O1	0.0228 (12)	0.0213 (12)	0.0204 (12)	−0.0058 (10)	0.0141 (10)	−0.0004 (10)
O2	0.0211 (11)	0.0176 (11)	0.0178 (11)	−0.0034 (9)	0.0145 (9)	0.0006 (9)
C1	0.0288 (18)	0.0257 (19)	0.0308 (19)	0.0052 (14)	0.0217 (16)	0.0083 (15)
C2	0.023 (5)	0.009 (4)	0.025 (5)	0.000 (4)	0.012 (4)	0.008 (4)
C3	0.024 (4)	0.019 (4)	0.018 (4)	−0.010 (3)	0.013 (3)	0.000 (3)
C4	0.023 (3)	0.029 (4)	0.017 (3)	−0.001 (3)	0.011 (3)	0.001 (3)
C5	0.017 (3)	0.028 (4)	0.029 (4)	0.005 (3)	0.013 (3)	0.014 (4)
C6	0.022 (4)	0.023 (4)	0.023 (4)	−0.009 (3)	0.007 (3)	0.010 (3)
C7	0.027 (4)	0.016 (4)	0.017 (4)	−0.005 (3)	0.014 (3)	−0.001 (3)
C2'	0.025 (6)	0.019 (5)	0.017 (4)	0.004 (4)	0.018 (4)	0.002 (4)
C3'	0.031 (5)	0.021 (4)	0.023 (4)	−0.004 (3)	0.016 (4)	−0.003 (3)
C4'	0.037 (5)	0.032 (4)	0.028 (4)	0.006 (4)	0.026 (4)	−0.002 (4)
C5'	0.028 (4)	0.033 (4)	0.035 (5)	0.004 (3)	0.024 (4)	0.010 (4)
C6'	0.023 (3)	0.032 (4)	0.026 (4)	0.003 (3)	0.012 (3)	0.004 (3)
C7'	0.024 (4)	0.022 (4)	0.012 (3)	−0.005 (3)	0.013 (3)	0.001 (3)
C8	0.0234 (17)	0.0237 (18)	0.0258 (18)	−0.0008 (14)	0.0141 (15)	0.0019 (14)
C9	0.0186 (15)	0.0239 (17)	0.0131 (14)	−0.0027 (13)	0.0061 (12)	0.0018 (13)
C10	0.0263 (17)	0.0274 (19)	0.0233 (17)	−0.0002 (15)	0.0140 (15)	0.0007 (15)
C11	0.0202 (16)	0.032 (2)	0.0310 (19)	−0.0012 (15)	0.0152 (15)	0.0036 (16)
C12	0.0171 (16)	0.036 (2)	0.0262 (19)	−0.0058 (15)	0.0064 (14)	0.0020 (16)
C13	0.0201 (16)	0.0267 (19)	0.0206 (17)	−0.0071 (13)	0.0047 (14)	−0.0063 (14)
C14	0.0202 (16)	0.0261 (18)	0.0179 (16)	−0.0005 (13)	0.0090 (13)	−0.0009 (13)
C15	0.0310 (19)	0.0249 (19)	0.041 (2)	0.0145 (15)	0.0271 (17)	0.0182 (16)
C16	0.0155 (15)	0.0196 (17)	0.0331 (19)	0.0043 (13)	0.0148 (14)	0.0068 (14)
C17	0.027 (2)	0.022 (2)	0.055 (3)	−0.0061 (16)	−0.0030 (19)	0.015 (2)
C18	0.043 (3)	0.019 (2)	0.043 (3)	−0.0004 (18)	−0.017 (2)	−0.0012 (19)
C19	0.032 (2)	0.031 (2)	0.0193 (18)	0.0152 (17)	0.0018 (16)	0.0017 (16)
C20	0.0198 (16)	0.0273 (19)	0.0231 (17)	0.0038 (14)	0.0118 (14)	0.0055 (14)
C21	0.0221 (16)	0.0234 (17)	0.0222 (16)	−0.0017 (13)	0.0132 (14)	−0.0005 (14)
C22	0.0193 (16)	0.042 (2)	0.0158 (16)	−0.0063 (15)	0.0093 (14)	0.0031 (15)
C23	0.0196 (15)	0.0276 (18)	0.0119 (14)	−0.0072 (13)	0.0081 (12)	−0.0032 (13)
C24	0.0271 (17)	0.0284 (19)	0.0252 (18)	0.0011 (15)	0.0171 (15)	0.0019 (15)
C25	0.0343 (19)	0.0260 (19)	0.0236 (18)	0.0033 (15)	0.0163 (16)	0.0077 (15)
C26	0.0284 (17)	0.0239 (18)	0.0172 (16)	−0.0084 (14)	0.0138 (14)	−0.0050 (13)
C27	0.0252 (17)	0.031 (2)	0.0267 (18)	0.0005 (15)	0.0172 (15)	0.0001 (16)
C28	0.0260 (18)	0.0260 (19)	0.0231 (18)	0.0028 (14)	0.0141 (15)	0.0022 (14)
C29	0.029 (4)	0.031 (5)	0.039 (5)	0.001 (4)	0.017 (4)	−0.003 (4)
C30	0.026 (3)	0.025 (4)	0.018 (3)	0.001 (3)	0.006 (3)	0.002 (3)
C31	0.035 (5)	0.026 (3)	0.031 (6)	0.003 (4)	0.015 (5)	−0.001 (3)
C32	0.058 (5)	0.036 (4)	0.032 (4)	−0.013 (4)	0.021 (4)	0.002 (3)
C33	0.033 (4)	0.050 (5)	0.027 (4)	−0.008 (4)	0.013 (3)	0.003 (4)
C34	0.038 (6)	0.036 (6)	0.021 (4)	−0.003 (4)	0.007 (4)	−0.002 (4)
C35	0.033 (4)	0.023 (4)	0.025 (3)	0.000 (3)	0.014 (4)	0.000 (3)

Geometric parameters (Å, º) top

Sn1—O2	2.023 (2)	C10—H10	0.9500
Sn1—C8	2.140 (4)	C11—C12	1.3900
Sn1—C1	2.154 (4)	C11—H11	0.9500
Sn1—O1	2.215 (2)	C12—C13	1.3900
Sn1—Cl5	2.4834 (8)	C13—C14	1.3900
Sn2—O2	2.047 (2)	C13—H13	0.9500
Sn2—O2ⁱ	2.129 (2)	C14—H14	0.9500
Sn2—C22	2.135 (3)	C15—C16	1.512 (4)
Sn2—C15	2.141 (3)	C15—H15A	0.9900
Sn2—O1	2.173 (2)	C15—H15B	0.9900
Cl1—C5	1.725 (4)	C16—C17	1.3900
Cl1'—C5'	1.730 (4)	C16—C21	1.3900
Cl2—C12	1.7292 (17)	C17—C18	1.3900
Cl3—C19	1.733 (2)	C17—H17	0.9500
Cl4—C26	1.7335 (16)	C18—C19	1.3900
O1—H2	0.8400	C18—H18	0.9500
O2—Sn2ⁱ	2.129 (2)	C19—C20	1.3900
C1—C2'	1.495 (5)	C20—C21	1.3900
C1—C2	1.505 (4)	C20—H20	0.9500
C1—H1A	0.9900	C21—H21	0.9500
C1—H1B	0.9900	C22—C23	1.518 (4)
C1—H1C	0.9900	C22—H22A	0.9900
C1—H1D	0.9901	C22—H22B	0.9900
C2—C3	1.3900	C23—C24	1.3900
C2—C7	1.3900	C23—C28	1.3900
C3—C4	1.3900	C24—C25	1.3900
C3—H3	0.9500	C24—H24	0.9500
C4—C5	1.3900	C25—C26	1.3900
C4—H4	0.9500	C25—H25	0.9500
C5—C6	1.3900	C26—C27	1.3900
C6—C7	1.3900	C27—C28	1.3900
C6—H6	0.9500	C27—H27	0.9500
C7—H7	0.9500	C28—H28	0.9500
C2'—C3'	1.3900	C29—C30	1.493 (10)
C2'—C7'	1.3900	C29—H29A	0.9800
C3'—C4'	1.3900	C29—H29B	0.9800
C3'—H3'	0.9500	C29—H29C	0.9800
C4'—C5'	1.3900	C30—C31	1.3900
C4'—H4'	0.9500	C30—C35	1.3900
C5'—C6'	1.3900	C31—C32	1.3900
C6'—C7'	1.3900	C31—H31	0.9500
C6'—H6'	0.9500	C32—C33	1.3900
C7'—H7'	0.9500	C32—H32	0.9500
C8—C9	1.512 (4)	C33—C34	1.3900
C8—H8A	0.9900	C33—H33	0.9500
C8—H8B	0.9900	C34—C35	1.3900
C9—C10	1.3900	C34—H34	0.9500
C9—C14	1.3900	C35—H35	0.9500
C10—C11	1.3900

O2—Sn1—C8	111.30 (12)	C10—C9—C14	120.0
O2—Sn1—C1	119.52 (12)	C10—C9—C8	120.45 (19)
C8—Sn1—C1	128.14 (14)	C14—C9—C8	119.54 (19)
O2—Sn1—O1	73.60 (8)	C9—C10—C11	120.0
C8—Sn1—O1	93.91 (12)	C9—C10—H10	120.0
C1—Sn1—O1	90.90 (12)	C11—C10—H10	120.0
O2—Sn1—Cl5	86.57 (6)	C10—C11—C12	120.0
C8—Sn1—Cl5	95.92 (10)	C10—C11—H11	120.0
C1—Sn1—Cl5	96.62 (10)	C12—C11—H11	120.0
O1—Sn1—Cl5	159.98 (6)	C13—C12—C11	120.0
O2—Sn2—O2ⁱ	73.49 (10)	C13—C12—Cl2	120.27 (14)
O2—Sn2—C22	118.21 (13)	C11—C12—Cl2	119.73 (14)
O2ⁱ—Sn2—C22	96.37 (11)	C14—C13—C12	120.0
O2—Sn2—C15	117.40 (14)	C14—C13—H13	120.0
O2ⁱ—Sn2—C15	101.99 (11)	C12—C13—H13	120.0
C22—Sn2—C15	124.29 (16)	C13—C14—C9	120.0
O2—Sn2—O1	74.04 (8)	C13—C14—H14	120.0
O2ⁱ—Sn2—O1	147.53 (9)	C9—C14—H14	120.0
C22—Sn2—O1	98.35 (11)	C16—C15—Sn2	114.6 (2)
C15—Sn2—O1	93.30 (12)	C16—C15—H15A	108.6
Sn2—O1—Sn1	100.39 (9)	Sn2—C15—H15A	108.6
Sn2—O1—H2	129.8	C16—C15—H15B	108.6
Sn1—O1—H2	129.8	Sn2—C15—H15B	108.6
Sn1—O2—Sn2	111.85 (9)	H15A—C15—H15B	107.6
Sn1—O2—Sn2ⁱ	141.49 (12)	C17—C16—C21	120.0
Sn2—O2—Sn2ⁱ	106.51 (10)	C17—C16—C15	120.2 (2)
C2'—C1—Sn1	112.0 (4)	C21—C16—C15	119.8 (2)
C2—C1—Sn1	112.2 (4)	C16—C17—C18	120.0
C2'—C1—H1A	115.4	C16—C17—H17	120.0
C2—C1—H1A	109.2	C18—C17—H17	120.0
Sn1—C1—H1A	109.2	C19—C18—C17	120.0
C2'—C1—H1B	102.9	C19—C18—H18	120.0
C2—C1—H1B	109.2	C17—C18—H18	120.0
Sn1—C1—H1B	109.2	C18—C19—C20	120.0
H1A—C1—H1B	107.9	C18—C19—Cl3	120.66 (16)
C2'—C1—H1C	108.4	C20—C19—Cl3	119.34 (16)
C2—C1—H1C	101.8	C21—C20—C19	120.0
Sn1—C1—H1C	108.8	C21—C20—H20	120.0
C2'—C1—H1D	110.5	C19—C20—H20	120.0
C2—C1—H1D	116.4	C20—C21—C16	120.0
Sn1—C1—H1D	109.3	C20—C21—H21	120.0
H1C—C1—H1D	107.8	C16—C21—H21	120.0
C3—C2—C7	120.0	C23—C22—Sn2	115.0 (2)
C3—C2—C1	116.4 (4)	C23—C22—H22A	108.5
C7—C2—C1	123.6 (4)	Sn2—C22—H22A	108.5
C2—C3—C4	120.0	C23—C22—H22B	108.5
C2—C3—H3	120.0	Sn2—C22—H22B	108.5
C4—C3—H3	120.0	H22A—C22—H22B	107.5
C5—C4—C3	120.0	C24—C23—C28	120.0
C5—C4—H4	120.0	C24—C23—C22	119.5 (2)
C3—C4—H4	120.0	C28—C23—C22	120.5 (2)
C4—C5—C6	120.0	C25—C24—C23	120.0
C4—C5—Cl1	120.6 (4)	C25—C24—H24	120.0
C6—C5—Cl1	119.4 (4)	C23—C24—H24	120.0
C7—C6—C5	120.0	C24—C25—C26	120.0
C7—C6—H6	120.0	C24—C25—H25	120.0
C5—C6—H6	120.0	C26—C25—H25	120.0
C6—C7—C2	120.0	C27—C26—C25	120.0
C6—C7—H7	120.0	C27—C26—Cl4	119.67 (13)
C2—C7—H7	120.0	C25—C26—Cl4	120.28 (13)
C3'—C2'—C7'	120.0	C26—C27—C28	120.0
C3'—C2'—C1	124.7 (4)	C26—C27—H27	120.0
C7'—C2'—C1	115.2 (4)	C28—C27—H27	120.0
C2'—C3'—C4'	120.0	C27—C28—C23	120.0
C2'—C3'—H3'	120.0	C27—C28—H28	120.0
C4'—C3'—H3'	120.0	C23—C28—H28	120.0
C5'—C4'—C3'	120.0	C31—C30—C35	120.0
C5'—C4'—H4'	120.0	C31—C30—C29	119.7 (7)
C3'—C4'—H4'	120.0	C35—C30—C29	120.3 (7)
C4'—C5'—C6'	120.0	C30—C31—C32	120.0
C4'—C5'—Cl1'	121.1 (4)	C30—C31—H31	120.0
C6'—C5'—Cl1'	118.9 (4)	C32—C31—H31	120.0
C5'—C6'—C7'	120.0	C31—C32—C33	120.0
C5'—C6'—H6'	120.0	C31—C32—H32	120.0
C7'—C6'—H6'	120.0	C33—C32—H32	120.0
C6'—C7'—C2'	120.0	C34—C33—C32	120.0
C6'—C7'—H7'	120.0	C34—C33—H33	120.0
C2'—C7'—H7'	120.0	C32—C33—H33	120.0
C9—C8—Sn1	114.0 (2)	C33—C34—C35	120.0
C9—C8—H8A	108.8	C33—C34—H34	120.0
Sn1—C8—H8A	108.8	C35—C34—H34	120.0
C9—C8—H8B	108.8	C34—C35—C30	120.0
Sn1—C8—H8B	108.8	C34—C35—H35	120.0
H8A—C8—H8B	107.6	C30—C35—H35	120.0

O2—Sn2—O1—Sn1	−2.43 (8)	C1—C2'—C7'—C6'	177.6 (7)
O2ⁱ—Sn2—O1—Sn1	−1.4 (2)	O2—Sn1—C8—C9	−176.63 (19)
C22—Sn2—O1—Sn1	114.63 (13)	C1—Sn1—C8—C9	15.2 (3)
C15—Sn2—O1—Sn1	−120.01 (13)	O1—Sn1—C8—C9	109.5 (2)
O2—Sn1—O1—Sn2	2.47 (9)	Cl5—Sn1—C8—C9	−88.0 (2)
C8—Sn1—O1—Sn2	113.53 (12)	Sn1—C8—C9—C10	−108.9 (2)
C1—Sn1—O1—Sn2	−118.14 (12)	Sn1—C8—C9—C14	70.2 (3)
Cl5—Sn1—O1—Sn2	−5.8 (3)	C14—C9—C10—C11	0.0
C8—Sn1—O2—Sn2	−90.57 (14)	C8—C9—C10—C11	179.1 (2)
C1—Sn1—O2—Sn2	78.73 (16)	C9—C10—C11—C12	0.0
O1—Sn1—O2—Sn2	−2.78 (10)	C10—C11—C12—C13	0.0
Cl5—Sn1—O2—Sn2	174.40 (10)	C10—C11—C12—Cl2	−179.31 (19)
C8—Sn1—O2—Sn2ⁱ	94.6 (2)	C11—C12—C13—C14	0.0
C1—Sn1—O2—Sn2ⁱ	−96.1 (2)	Cl2—C12—C13—C14	179.30 (19)
O1—Sn1—O2—Sn2ⁱ	−177.6 (2)	C12—C13—C14—C9	0.0
Cl5—Sn1—O2—Sn2ⁱ	−0.40 (18)	C10—C9—C14—C13	0.0
O2ⁱ—Sn2—O2—Sn1	−176.62 (18)	C8—C9—C14—C13	−179.1 (2)
C22—Sn2—O2—Sn1	−88.21 (14)	O2—Sn2—C15—C16	37.0 (3)
C15—Sn2—O2—Sn1	88.19 (15)	O2ⁱ—Sn2—C15—C16	−40.4 (3)
O1—Sn2—O2—Sn1	2.82 (10)	C22—Sn2—C15—C16	−146.8 (2)
O2ⁱ—Sn2—O2—Sn2ⁱ	0.0	O1—Sn2—C15—C16	110.8 (2)
C22—Sn2—O2—Sn2ⁱ	88.41 (14)	Sn2—C15—C16—C17	−80.2 (3)
C15—Sn2—O2—Sn2ⁱ	−95.18 (14)	Sn2—C15—C16—C21	101.8 (2)
O1—Sn2—O2—Sn2ⁱ	179.45 (12)	C21—C16—C17—C18	0.0
O2—Sn1—C1—C2'	−145.1 (3)	C15—C16—C17—C18	−177.9 (2)
C8—Sn1—C1—C2'	22.2 (4)	C16—C17—C18—C19	0.0
O1—Sn1—C1—C2'	−73.5 (3)	C17—C18—C19—C20	0.0
Cl5—Sn1—C1—C2'	125.1 (3)	C17—C18—C19—Cl3	−179.7 (2)
O2—Sn1—C1—C2	−137.2 (3)	C18—C19—C20—C21	0.0
C8—Sn1—C1—C2	30.1 (4)	Cl3—C19—C20—C21	179.7 (2)
O1—Sn1—C1—C2	−65.6 (3)	C19—C20—C21—C16	0.0
Cl5—Sn1—C1—C2	133.0 (3)	C17—C16—C21—C20	0.0
C2'—C1—C2—C3	−170 (5)	C15—C16—C21—C20	177.9 (2)
Sn1—C1—C2—C3	100.5 (4)	O2—Sn2—C22—C23	98.0 (3)
C2'—C1—C2—C7	7 (5)	O2ⁱ—Sn2—C22—C23	172.7 (2)
Sn1—C1—C2—C7	−81.9 (5)	C15—Sn2—C22—C23	−78.1 (3)
C7—C2—C3—C4	0.0	O1—Sn2—C22—C23	21.7 (3)
C1—C2—C3—C4	177.7 (6)	Sn2—C22—C23—C24	−129.00 (19)
C2—C3—C4—C5	0.0	Sn2—C22—C23—C28	54.1 (3)
C3—C4—C5—C6	0.0	C28—C23—C24—C25	0.0
C3—C4—C5—Cl1	−178.6 (5)	C22—C23—C24—C25	−176.9 (2)
C4—C5—C6—C7	0.0	C23—C24—C25—C26	0.0
Cl1—C5—C6—C7	178.7 (5)	C24—C25—C26—C27	0.0
C5—C6—C7—C2	0.0	C24—C25—C26—Cl4	177.44 (18)
C3—C2—C7—C6	0.0	C25—C26—C27—C28	0.0
C1—C2—C7—C6	−177.5 (7)	Cl4—C26—C27—C28	−177.45 (18)
Sn1—C1—C2'—C3'	93.2 (5)	C26—C27—C28—C23	0.0
C2—C1—C2'—C7'	−178 (5)	C24—C23—C28—C27	0.0
Sn1—C1—C2'—C7'	−84.3 (4)	C22—C23—C28—C27	176.9 (2)
C7'—C2'—C3'—C4'	0.0	C35—C30—C31—C32	0.0
C1—C2'—C3'—C4'	−177.4 (7)	C29—C30—C31—C32	179.6 (9)
C2'—C3'—C4'—C5'	0.0	C30—C31—C32—C33	0.0
C3'—C4'—C5'—C6'	0.0	C31—C32—C33—C34	0.0
C3'—C4'—C5'—Cl1'	179.7 (5)	C32—C33—C34—C35	0.0
C4'—C5'—C6'—C7'	0.0	C33—C34—C35—C30	0.0
Cl1'—C5'—C6'—C7'	−179.7 (5)	C31—C30—C35—C34	0.0
C5'—C6'—C7'—C2'	0.0	C29—C30—C35—C34	−179.6 (9)
C3'—C2'—C7'—C6'	0.0

Symmetry code: (i) −x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Sn₄(C₇H₆Cl)₈Cl₂O₂(OH)₂]·C₇H₈
M_r	1708.35
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	26.6531 (3), 10.8342 (1), 25.8025 (3)
β (°)	121.546 (1)
V (Å³)	6349.8 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.02
Crystal size (mm)	0.36 × 0.12 × 0.08

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.564, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	21584, 7288, 6556
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.118, 0.97
No. of reflections	7288
No. of parameters	389
No. of restraints	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.08, −1.53

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank the University of Malaya (FS339/2008 A) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mohamed, E. M., Panchanatheswaran, K., Low, J. N. & Glidewell, C. (2004). Acta Cryst. E60, m489–m491. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shishido, K., Yoshiyuki, T. & Jiro, K. (1961). J. Am. Chem. Soc. 83, 538–541. CAS Google Scholar
Wang, J.-Q., Zhang, F.-X., Kuang, D.-Z., Feng, Y.-L., Xu, Z.-F. & Chen, Z.-M. (2007). Chin. J. Inorg. Chem. 23, 871–874. CAS Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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