Dibromidodi-μ-hydroxido-di-μ3-oxido-octa­phenyl­tetra­tin(IV)

Yap, Q.L.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536809051691

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m8

doi:10.1107/S1600536809051691

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Dibromidodi-μ-hydroxido-di-μ₃-oxido-octaphenyltetratin(IV)

Quai Ling Yap,^a 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 16 November 2009; accepted 1 December 2009; online 4 December 2009)

In the centrosymmetric title compound, [Sn₄Br₂(C₆H₅)₈O₂(OH)₂], the four tin(IV) atoms are bridged by the hydroxo and oxo ligands, forming a ladder-like array of three edge-connected Sn₂O₂ squares. The two independent tin atoms show distorted trigonal-bipyramidal SnC₂O₃ and SnC₂O₂Br coordination geometries.

Related literature

For other [Sn₄X₂(O)₂(OH)₂R₈] (X = halogen, R = organic group) structures, see: Baumeister et al. (2002 ); Beckmann et al. (2001 ); Cox & Tiekink (1994 ); Kresinski et al. (1994 ); Lo & Ng (2009 ); Mohamed et al. (2004 ); Puff et al. (1983 ); Tiekink (1991 ); Vollano et al. (1984 ).

Experimental

Crystal data

[Sn₄Br₂(C₆H₅)₈O₂(OH)₂]
M_r = 1317.40
Triclinic, $[P \overline 1]$
a = 10.3759 (1) Å
b = 10.8247 (1) Å
c = 12.0341 (2) Å
α = 77.1809 (7)°
β = 65.4426 (7)°
γ = 75.2040 (7)°
V = 1178.26 (3) Å³
Z = 1
Mo Kα radiation
μ = 3.83 mm⁻¹
T = 293 K
0.25 × 0.25 × 0.25 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.539, T_max = 0.746
10751 measured reflections
5309 independent reflections
4449 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.160
S = 1.06
5309 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 2.39 e Å⁻³
Δρ_min = −1.38 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—O1ⁱ	2.068 (4)
Sn1—O1	2.095 (4)
Sn1—C1	2.117 (6)
Sn1—C7	2.120 (6)
Sn1—O2	2.171 (4)
Sn2—O1ⁱ	2.029 (4)
Sn2—C13	2.118 (7)
Sn2—C19	2.126 (7)
Sn2—O2	2.167 (4)
Sn2—Br1	2.6444 (9)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 software (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/S1600536809051691/hb5234sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051691/hb5234Isup2.hkl

checkCIF report

Related literature top

For other [Sn₄X₂(O)₂(OH)₂R₈] (X = halogen, R = organic group) structures, see: Baumeister et al. (2002); Beckmann et al. (2001); Cox & Tiekink (1994); Kresinski et al. (1994); Lo & Ng (2009); Mohamed et al. (2004); Puff et al. (1983); Tiekink (1991); Vollano et al. (1984).

Experimental top

In an attempt to cleave a tin-carbon bond in a tetraorganotin compound, bis(3-methyl-2-thienyl)diphenyltin (0.47 g,1 mmol) and trimethylphenylammonium tribromide (0.38 g, 1 mmol) were heated in ethanol for three hours. Colourless blocks of (I) separated from solution after a few days.

Computing details top

Data collection: APEX2 software (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. View of (I) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. Unlabelled atoms are generated by the symmetry operation (1–x, 1–y, 1–z).

Dibromidodi-µ-hydroxido-di-µ₃-oxido-octaphenyltetratin(IV) top

Crystal data top

[Sn₄Br₂(C₆H₅)₈O₂(OH)₂]	Z = 1
M_r = 1317.40	F(000) = 632
Triclinic, P1	D_x = 1.857 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.3759 (1) Å	Cell parameters from 7354 reflections
b = 10.8247 (1) Å	θ = 2.2–28.5°
c = 12.0341 (2) Å	µ = 3.83 mm⁻¹
α = 77.1809 (7)°	T = 293 K
β = 65.4426 (7)°	Block, colourless
γ = 75.2040 (7)°	0.25 × 0.25 × 0.25 mm
V = 1178.26 (3) Å³

Data collection top

Bruker SMART APEX diffractometer	5309 independent reflections
Radiation source: fine-focus sealed tube	4449 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.539, T_max = 0.746	k = −14→13
10751 measured reflections	l = −15→15

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0952P)² + 4.7584P] where P = (F_o² + 2F_c²)/3
5309 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 2.39 e Å⁻³
0 restraints	Δρ_min = −1.38 e Å⁻³

Crystal data top

[Sn₄Br₂(C₆H₅)₈O₂(OH)₂]	γ = 75.2040 (7)°
M_r = 1317.40	V = 1178.26 (3) Å³
Triclinic, P1	Z = 1
a = 10.3759 (1) Å	Mo Kα radiation
b = 10.8247 (1) Å	µ = 3.83 mm⁻¹
c = 12.0341 (2) Å	T = 293 K
α = 77.1809 (7)°	0.25 × 0.25 × 0.25 mm
β = 65.4426 (7)°

Data collection top

Bruker SMART APEX diffractometer	5309 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4449 reflections with I > 2σ(I)
T_min = 0.539, T_max = 0.746	R_int = 0.028
10751 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.06	Δρ_max = 2.39 e Å⁻³
5309 reflections	Δρ_min = −1.38 e Å⁻³
262 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.38584 (4)	0.45011 (4)	0.46172 (4)	0.03147 (14)
Sn2	0.52171 (5)	0.20525 (4)	0.63535 (4)	0.03495 (15)
Br1	0.70321 (9)	0.23768 (8)	0.72424 (7)	0.0508 (2)
O1	0.4796 (5)	0.6078 (4)	0.4416 (4)	0.0315 (8)
O2	0.3774 (5)	0.2494 (4)	0.5377 (4)	0.0364 (9)
H2O	0.3312	0.2022	0.5311	0.044*
C1	0.4869 (8)	0.4083 (7)	0.2777 (6)	0.0437 (15)
C2	0.6000 (10)	0.4680 (9)	0.1951 (7)	0.062 (2)
H2	0.6262	0.5303	0.2198	0.074*
C3	0.6748 (14)	0.4366 (14)	0.0765 (9)	0.092 (4)
H3	0.7537	0.4739	0.0230	0.111*
C4	0.6308 (17)	0.3499 (15)	0.0393 (11)	0.104 (5)
H4	0.6786	0.3303	−0.0410	0.125*
C5	0.5169 (15)	0.2913 (12)	0.1190 (11)	0.088 (4)
H5	0.4865	0.2338	0.0921	0.106*
C6	0.4471 (11)	0.3183 (9)	0.2404 (8)	0.060 (2)
H6	0.3736	0.2753	0.2959	0.072*
C7	0.1737 (7)	0.5207 (7)	0.5813 (6)	0.0379 (13)
C8	0.0633 (8)	0.4546 (8)	0.6167 (8)	0.0524 (18)
H8	0.0782	0.3810	0.5819	0.063*
C9	−0.0724 (10)	0.4978 (12)	0.7057 (10)	0.075 (3)
H9	−0.1485	0.4550	0.7284	0.090*
C10	−0.0900 (10)	0.6034 (13)	0.7578 (9)	0.082 (3)
H10	−0.1780	0.6296	0.8196	0.098*
C11	0.0158 (11)	0.6711 (12)	0.7228 (11)	0.084 (3)
H11	−0.0008	0.7451	0.7576	0.100*
C12	0.1506 (9)	0.6298 (9)	0.6340 (8)	0.0554 (19)
H12	0.2247	0.6754	0.6103	0.067*
C13	0.3559 (8)	0.1680 (7)	0.8092 (6)	0.0453 (15)
C14	0.3843 (12)	0.0721 (11)	0.8954 (9)	0.077 (3)
H14	0.4784	0.0286	0.8804	0.093*
C15	0.2745 (16)	0.0389 (14)	1.0052 (10)	0.103 (4)
H15	0.2949	−0.0282	1.0623	0.123*
C16	0.1375 (15)	0.1039 (13)	1.0295 (10)	0.091 (4)
H16	0.0637	0.0796	1.1022	0.109*
C17	0.1077 (13)	0.2043 (14)	0.9484 (10)	0.094 (4)
H17	0.0144	0.2512	0.9670	0.113*
C18	0.2175 (10)	0.2370 (10)	0.8367 (8)	0.065 (2)
H18	0.1971	0.3056	0.7809	0.078*
C19	0.6770 (7)	0.0737 (6)	0.5153 (6)	0.0388 (13)
C20	0.7810 (9)	−0.0145 (8)	0.5494 (8)	0.0527 (18)
H20	0.7787	−0.0227	0.6288	0.063*
C21	0.8893 (9)	−0.0909 (9)	0.4642 (9)	0.062 (2)
H21	0.9578	−0.1515	0.4879	0.074*
C22	0.8961 (9)	−0.0784 (8)	0.3475 (9)	0.059 (2)
H22	0.9705	−0.1285	0.2911	0.071*
C23	0.7926 (9)	0.0089 (8)	0.3123 (8)	0.0541 (19)
H23	0.7975	0.0177	0.2321	0.065*
C24	0.6816 (9)	0.0834 (7)	0.3962 (7)	0.0495 (17)
H24	0.6101	0.1399	0.3732	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0317 (2)	0.0315 (2)	0.0317 (2)	−0.00616 (16)	−0.01214 (17)	−0.00462 (15)
Sn2	0.0381 (2)	0.0287 (2)	0.0345 (2)	−0.00560 (17)	−0.01235 (18)	−0.00091 (16)
Br1	0.0555 (4)	0.0517 (4)	0.0531 (4)	−0.0067 (3)	−0.0305 (3)	−0.0063 (3)
O1	0.033 (2)	0.026 (2)	0.036 (2)	−0.0070 (16)	−0.0157 (17)	0.0008 (16)
O2	0.040 (2)	0.030 (2)	0.045 (2)	−0.0123 (18)	−0.0197 (19)	−0.0005 (17)
C1	0.055 (4)	0.039 (3)	0.033 (3)	0.000 (3)	−0.017 (3)	−0.008 (3)
C2	0.068 (5)	0.070 (6)	0.040 (4)	−0.024 (5)	−0.006 (4)	−0.010 (4)
C3	0.104 (9)	0.114 (10)	0.041 (5)	−0.033 (8)	−0.002 (5)	−0.014 (5)
C4	0.127 (11)	0.120 (11)	0.050 (6)	−0.001 (9)	−0.019 (7)	−0.036 (6)
C5	0.123 (10)	0.082 (7)	0.080 (7)	0.005 (7)	−0.055 (7)	−0.046 (6)
C6	0.069 (5)	0.061 (5)	0.061 (5)	−0.005 (4)	−0.032 (4)	−0.024 (4)
C7	0.031 (3)	0.041 (3)	0.038 (3)	−0.005 (3)	−0.012 (2)	−0.004 (3)
C8	0.039 (4)	0.049 (4)	0.066 (5)	−0.010 (3)	−0.017 (3)	−0.005 (3)
C9	0.044 (5)	0.096 (8)	0.077 (6)	−0.024 (5)	−0.016 (4)	0.002 (6)
C10	0.044 (5)	0.114 (9)	0.061 (6)	−0.008 (5)	0.006 (4)	−0.018 (6)
C11	0.058 (6)	0.086 (8)	0.090 (7)	−0.003 (5)	−0.001 (5)	−0.046 (6)
C12	0.042 (4)	0.059 (5)	0.060 (5)	−0.011 (4)	−0.007 (3)	−0.021 (4)
C13	0.051 (4)	0.043 (4)	0.038 (3)	−0.016 (3)	−0.010 (3)	−0.003 (3)
C14	0.075 (6)	0.073 (6)	0.059 (5)	−0.011 (5)	−0.019 (5)	0.023 (5)
C15	0.110 (10)	0.107 (10)	0.058 (6)	−0.033 (8)	−0.015 (6)	0.033 (6)
C16	0.101 (9)	0.094 (8)	0.049 (5)	−0.038 (7)	0.010 (5)	−0.009 (5)
C17	0.069 (7)	0.115 (10)	0.065 (6)	−0.025 (7)	0.016 (5)	−0.024 (7)
C18	0.058 (5)	0.068 (6)	0.053 (5)	−0.009 (4)	−0.009 (4)	−0.005 (4)
C19	0.036 (3)	0.030 (3)	0.050 (4)	−0.007 (3)	−0.016 (3)	−0.008 (3)
C20	0.054 (4)	0.046 (4)	0.060 (5)	−0.002 (3)	−0.025 (4)	−0.012 (3)
C21	0.051 (5)	0.048 (5)	0.087 (6)	0.011 (4)	−0.031 (4)	−0.024 (4)
C22	0.040 (4)	0.051 (5)	0.081 (6)	−0.003 (3)	−0.013 (4)	−0.023 (4)
C23	0.054 (4)	0.058 (5)	0.048 (4)	−0.018 (4)	−0.009 (3)	−0.014 (3)
C24	0.052 (4)	0.038 (4)	0.055 (4)	−0.002 (3)	−0.019 (3)	−0.010 (3)

Geometric parameters (Å, º) top

Sn1—O1ⁱ	2.068 (4)	C9—H9	0.9300
Sn1—O1	2.095 (4)	C10—C11	1.345 (16)
Sn1—C1	2.117 (6)	C10—H10	0.9300
Sn1—C7	2.120 (6)	C11—C12	1.396 (12)
Sn1—O2	2.171 (4)	C11—H11	0.9300
Sn2—O1ⁱ	2.029 (4)	C12—H12	0.9300
Sn2—C13	2.118 (7)	C13—C14	1.365 (11)
Sn2—C19	2.126 (7)	C13—C18	1.377 (12)
Sn2—O2	2.167 (4)	C14—C15	1.385 (14)
Sn2—Br1	2.6444 (9)	C14—H14	0.9300
O1—Sn2ⁱ	2.029 (4)	C15—C16	1.355 (18)
O1—Sn1ⁱ	2.068 (4)	C15—H15	0.9300
O2—H2O	0.8200	C16—C17	1.356 (19)
C1—C6	1.369 (11)	C16—H16	0.9300
C1—C2	1.384 (11)	C17—C18	1.397 (13)
C2—C3	1.384 (12)	C17—H17	0.9300
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.365 (19)	C19—C20	1.383 (10)
C3—H3	0.9300	C19—C24	1.394 (11)
C4—C5	1.37 (2)	C20—C21	1.393 (11)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.395 (13)	C21—C22	1.355 (13)
C5—H5	0.9300	C21—H21	0.9300
C6—H6	0.9300	C22—C23	1.381 (12)
C7—C12	1.384 (10)	C22—H22	0.9300
C7—C8	1.373 (10)	C23—C24	1.385 (11)
C8—C9	1.407 (12)	C23—H23	0.9300
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.360 (16)

O1ⁱ—Sn1—O1	73.05 (18)	C9—C8—H8	119.9
O1ⁱ—Sn1—C1	113.5 (2)	C10—C9—C8	118.7 (9)
O1—Sn1—C1	98.9 (2)	C10—C9—H9	120.6
O1ⁱ—Sn1—C7	109.8 (2)	C8—C9—H9	120.6
O1—Sn1—C7	98.4 (2)	C11—C10—C9	122.1 (9)
C1—Sn1—C7	136.4 (3)	C11—C10—H10	118.9
O1ⁱ—Sn1—O2	72.57 (17)	C9—C10—H10	118.9
O1—Sn1—O2	145.58 (17)	C10—C11—C12	119.7 (10)
C1—Sn1—O2	93.1 (2)	C10—C11—H11	120.2
C7—Sn1—O2	94.7 (2)	C12—C11—H11	120.2
O1ⁱ—Sn2—C13	116.9 (2)	C7—C12—C11	119.8 (8)
O1ⁱ—Sn2—C19	113.2 (2)	C7—C12—H12	120.1
C13—Sn2—C19	129.4 (3)	C11—C12—H12	120.1
O1ⁱ—Sn2—O2	73.38 (17)	C14—C13—C18	118.6 (8)
C13—Sn2—O2	93.3 (2)	C14—C13—Sn2	120.1 (7)
C19—Sn2—O2	94.0 (2)	C18—C13—Sn2	121.3 (6)
O1ⁱ—Sn2—Br1	86.33 (12)	C13—C14—C15	120.8 (10)
C13—Sn2—Br1	95.6 (2)	C13—C14—H14	119.6
C19—Sn2—Br1	94.25 (18)	C15—C14—H14	119.6
O2—Sn2—Br1	159.71 (12)	C16—C15—C14	120.1 (11)
Sn2ⁱ—O1—Sn1ⁱ	111.45 (19)	C16—C15—H15	120.0
Sn2ⁱ—O1—Sn1	141.6 (2)	C14—C15—H15	120.0
Sn1ⁱ—O1—Sn1	106.95 (18)	C17—C16—C15	120.3 (10)
Sn2—O2—Sn1	102.60 (18)	C17—C16—H16	119.9
Sn2—O2—H2O	128.7	C15—C16—H16	119.9
Sn1—O2—H2O	128.7	C16—C17—C18	119.8 (12)
C6—C1—C2	119.3 (7)	C16—C17—H17	120.1
C6—C1—Sn1	121.1 (6)	C18—C17—H17	120.1
C2—C1—Sn1	119.5 (6)	C13—C18—C17	120.2 (10)
C3—C2—C1	121.1 (9)	C13—C18—H18	119.9
C3—C2—H2	119.5	C17—C18—H18	119.9
C1—C2—H2	119.5	C20—C19—C24	119.3 (7)
C4—C3—C2	119.0 (11)	C20—C19—Sn2	121.2 (5)
C4—C3—H3	120.5	C24—C19—Sn2	119.4 (5)
C2—C3—H3	120.5	C19—C20—C21	119.6 (8)
C3—C4—C5	120.9 (10)	C19—C20—H20	120.2
C3—C4—H4	119.6	C21—C20—H20	120.2
C5—C4—H4	119.6	C22—C21—C20	121.0 (8)
C4—C5—C6	119.7 (11)	C22—C21—H21	119.5
C4—C5—H5	120.1	C20—C21—H21	119.5
C6—C5—H5	120.1	C21—C22—C23	119.9 (8)
C1—C6—C5	119.9 (10)	C21—C22—H22	120.0
C1—C6—H6	120.0	C23—C22—H22	120.0
C5—C6—H6	120.0	C24—C23—C22	120.1 (8)
C12—C7—C8	119.5 (7)	C24—C23—H23	119.9
C12—C7—Sn1	118.4 (5)	C22—C23—H23	119.9
C8—C7—Sn1	121.8 (5)	C23—C24—C19	120.0 (7)
C7—C8—C9	120.1 (9)	C23—C24—H24	120.0
C7—C8—H8	119.9	C19—C24—H24	120.0

O1ⁱ—Sn1—O1—Sn2ⁱ	−177.8 (5)	C12—C7—C8—C9	0.2 (12)
C1—Sn1—O1—Sn2ⁱ	70.2 (4)	Sn1—C7—C8—C9	173.6 (7)
C7—Sn1—O1—Sn2ⁱ	−69.5 (4)	C7—C8—C9—C10	−1.9 (15)
O2—Sn1—O1—Sn2ⁱ	179.3 (3)	C8—C9—C10—C11	3.2 (19)
O1ⁱ—Sn1—O1—Sn1ⁱ	0.0	C9—C10—C11—C12	−3 (2)
C1—Sn1—O1—Sn1ⁱ	−112.0 (2)	C8—C7—C12—C11	0.2 (13)
C7—Sn1—O1—Sn1ⁱ	108.2 (2)	Sn1—C7—C12—C11	−173.4 (8)
O2—Sn1—O1—Sn1ⁱ	−2.9 (4)	C10—C11—C12—C7	1.0 (17)
O1ⁱ—Sn2—O2—Sn1	−0.23 (16)	O1ⁱ—Sn2—C13—C14	−143.7 (8)
C13—Sn2—O2—Sn1	116.9 (3)	C19—Sn2—C13—C14	45.3 (9)
C19—Sn2—O2—Sn1	−113.2 (2)	O2—Sn2—C13—C14	143.2 (8)
Br1—Sn2—O2—Sn1	0.7 (5)	Br1—Sn2—C13—C14	−55.0 (8)
O1ⁱ—Sn1—O2—Sn2	0.23 (16)	O1ⁱ—Sn2—C13—C18	37.9 (8)
O1—Sn1—O2—Sn2	3.2 (4)	C19—Sn2—C13—C18	−133.2 (7)
C1—Sn1—O2—Sn2	113.9 (3)	O2—Sn2—C13—C18	−35.2 (7)
C7—Sn1—O2—Sn2	−109.1 (2)	Br1—Sn2—C13—C18	126.6 (7)
O1ⁱ—Sn1—C1—C6	112.1 (6)	C18—C13—C14—C15	4.3 (17)
O1—Sn1—C1—C6	−172.6 (6)	Sn2—C13—C14—C15	−174.2 (11)
C7—Sn1—C1—C6	−60.4 (8)	C13—C14—C15—C16	−2 (2)
O2—Sn1—C1—C6	39.7 (7)	C14—C15—C16—C17	−2 (2)
O1ⁱ—Sn1—C1—C2	−64.6 (7)	C15—C16—C17—C18	3 (2)
O1—Sn1—C1—C2	10.7 (7)	C14—C13—C18—C17	−3.3 (16)
C7—Sn1—C1—C2	122.9 (7)	Sn2—C13—C18—C17	175.2 (9)
O2—Sn1—C1—C2	−137.0 (7)	C16—C17—C18—C13	−0.3 (19)
C6—C1—C2—C3	−1.1 (15)	O1ⁱ—Sn2—C19—C20	123.9 (6)
Sn1—C1—C2—C3	175.6 (9)	C13—Sn2—C19—C20	−64.8 (7)
C1—C2—C3—C4	3.3 (19)	O2—Sn2—C19—C20	−162.4 (6)
C2—C3—C4—C5	−2 (2)	Br1—Sn2—C19—C20	36.1 (6)
C3—C4—C5—C6	−1 (2)	O1ⁱ—Sn2—C19—C24	−50.8 (6)
C2—C1—C6—C5	−2.4 (13)	C13—Sn2—C19—C24	120.5 (6)
Sn1—C1—C6—C5	−179.1 (8)	O2—Sn2—C19—C24	22.9 (6)
C4—C5—C6—C1	3.7 (17)	Br1—Sn2—C19—C24	−138.6 (6)
O1ⁱ—Sn1—C7—C12	63.6 (6)	C24—C19—C20—C21	0.7 (12)
O1—Sn1—C7—C12	−11.3 (6)	Sn2—C19—C20—C21	−174.0 (6)
C1—Sn1—C7—C12	−123.7 (6)	C19—C20—C21—C22	1.4 (14)
O2—Sn1—C7—C12	136.8 (6)	C20—C21—C22—C23	−1.7 (14)
O1ⁱ—Sn1—C7—C8	−109.8 (6)	C21—C22—C23—C24	−0.2 (13)
O1—Sn1—C7—C8	175.3 (6)	C22—C23—C24—C19	2.3 (12)
C1—Sn1—C7—C8	62.9 (7)	C20—C19—C24—C23	−2.5 (12)
O2—Sn1—C7—C8	−36.7 (6)	Sn2—C19—C24—C23	172.3 (6)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Sn₄Br₂(C₆H₅)₈O₂(OH)₂]
M_r	1317.40
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.3759 (1), 10.8247 (1), 12.0341 (2)
α, β, γ (°)	77.1809 (7), 65.4426 (7), 75.2040 (7)
V (Å³)	1178.26 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	3.83
Crystal size (mm)	0.25 × 0.25 × 0.25

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.539, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	10751, 5309, 4449
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.160, 1.06
No. of reflections	5309
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.39, −1.38

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

Selected bond lengths (Å) top

Sn1—O1ⁱ	2.068 (4)	Sn2—O1ⁱ	2.029 (4)
Sn1—O1	2.095 (4)	Sn2—C13	2.118 (7)
Sn1—C1	2.117 (6)	Sn2—C19	2.126 (7)
Sn1—C7	2.120 (6)	Sn2—O2	2.167 (4)
Sn1—O2	2.171 (4)	Sn2—Br1	2.6444 (9)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

References

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