Octa­methyl­bis­(μ2-2-methyl­benzoato-κ2O:O′)bis­(2-methyl­benzoato-κO)di-μ3-oxido-tetra­tin(IV)

Danish, M.; Ghafoor, S.; Tahir, M.N.; Ahmad, N.; Hamid, M.

doi:10.1107/S1600536810036512

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages m1268-m1269

doi:10.1107/S1600536810036512

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Octamethylbis(μ₂-2-methylbenzoato-κ²O:O′)bis(2-methylbenzoato-κO)di-μ₃-oxido-tetratin(IV)

Muhammad Danish,^a Sabiha Ghafoor,^a M. Nawaz Tahir,^b ^* Nazir Ahmad ^a and Masood Hamid ^a

^aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 30 August 2010; accepted 13 September 2010; online 18 September 2010)

The title compound, [Sn₄(CH₃)₈(C₈H₇O₂)₄O₂], is a distannoxane derivative of 2-methylbenzoic acid. The crystal structure is composed of centrosymmetric dimers lying about inversion centres. Both independent Sn atoms adopt distorted trigonal-bipyramidal SnC₂O₃ coordination geometries with the basal planes consisting of two C-atoms from the methyl groups and a bridging O atom. The Sn—C and Sn—O bond lengths lie in the ranges 2.090 (2)–2.104 (3) and 2.0241 (14)–2.2561 (15) Å, respectively. The central four-membered planar Sn₂O₂ ring [Sn⋯Sn distance = 3.2993 (2) Å] makes dihedral angles of 5.43 (11) and 59.50 (7)° with the methylphenyl groups, which are themselves oriented at a dihedral angle of 61.38 (8)°. Besides weak C—H⋯O and C—H⋯π interactions, the packing mainly features van der Waals forces between the molecules.

Related literature

For distannoxanes, see: Amini et al. (2002 ); Danish et al. (2009 ).

Experimental

Crystal data

[Sn₄(CH₃)₈(C₈H₇O₂)₄O₂]
M_r = 1167.66
Triclinic, $[P \overline 1]$
a = 10.0413 (2) Å
b = 10.1280 (2) Å
c = 12.0910 (3) Å
α = 83.300 (1)°
β = 72.850 (2)°
γ = 71.876 (1)°
V = 1116.24 (4) Å³
Z = 1
Mo Kα radiation
μ = 2.26 mm⁻¹
T = 296 K
0.30 × 0.26 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.514, T_max = 0.593
18376 measured reflections
5470 independent reflections
4786 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.018
wR(F²) = 0.049
S = 1.09
5470 reflections
250 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C14–C19 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10C⋯O5ⁱ	0.96	2.678	3.452 (3)	138
C4—H4⋯Cgⁱ	0.93	2.74	3.493 (3)	139
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036512/wm2399sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036512/wm2399Isup2.hkl

checkCIF report

Comment top

Recently we have reported the synthesis and crystal structure of a distannoxane (Danish et al., 2009). In continuation of our interest in tin chemistry, the title compound (I), (Fig. 1) has been synthesized and structurally characterized. The crystal structure of bis(1,1,3,3-tetramethyl-1,3-dibenzoatodistannoxane) (Amini et al., 2002) has also been published which is related to the title compound.

In the title molecule, both independent Sn atoms adopt distorted trigonal-bipyramidal coordination spheres with basal planes A (C9/C10/O3) and B (C11/C12/O3). The Sn—C and Sn—O bond lengths are lying in a range of 2.090 (2)–2.104 (3) Å and 2.0241 (14)–2.2561 (15) Å, respectively. The symmetry-related central four membered ring C (Sn2/O3/Sn2ⁱ/O3ⁱ; symmetry code: i = -x + 1, -y, -z + 1) is planar. The dihedral angles between A/C, B/C and A/B are 72.76 (4), 85.40 (6) and 57.54 (8)°, respectively. In (I), the 2-methylbenzoato ligands are not planar. In the endo ligand, group D (C2—C8) [r.m.s deviation of 0.0082 Å] is oriented at a dihedral angle of 32.9 (2)° with the carboxylato group E (O1/C1/O2). Whereas the exo ligand, group F (C14—C20) [r.m.s deviation of 0.0115 Å] is oriented at a dihedral angle of 45.3 (2)° with the carboxylato group G (O4/C13/O5). The dihedral angles between C/D and C/F are 5.43 (11) and 59.50 (7)°, respectively. There exist a weak C—H···O and a C—H···π interaction (Table 1). The packing mainly features van der Waals interactions between the molecules.

Related literature top

For distannoxanes, see: Amini et al. (2002); Danish et al. (2009).

Experimental top

The sodium salt of o-toluic acid (0.316 g, 2.0 mmol) was suspended in 25 ml dry methanol in a 100 ml round-bottom flask. To this suspension, dimethyl tin dichloride (0.22 g, 1 mmol), dissolved in 25 ml dry methanol, was added dropwise with constant stirring at room temperature. The reaction mixture was refluxed for 6 h. Filtration was carried out to remove sodium chloride formed during reaction. Colorless prism of (I) were obtained after 48 h from the filtrate. M.p 486 K; yield: 71%.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of the molecular structure of the title compound with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown as small spheres of arbitrary radius. [Symmetry code: (i) -x + 1, -y, -z + 1.]

Octamethylbis(µ₂-2-methylbenzoato-κ²O:O')bis(2- methylbenzoato-κO)di-µ₃-oxido-tetratin(IV) top

Crystal data top

[Sn₄(CH₃)₈(C₈H₇O₂)₄O₂]	Z = 1
M_r = 1167.66	F(000) = 572
Triclinic, P1	D_x = 1.737 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0413 (2) Å	Cell parameters from 4786 reflections
b = 10.1280 (2) Å	θ = 2.1–28.3°
c = 12.0910 (3) Å	µ = 2.26 mm⁻¹
α = 83.300 (1)°	T = 296 K
β = 72.850 (2)°	Prism, colorless
γ = 71.876 (1)°	0.30 × 0.26 × 0.23 mm
V = 1116.24 (4) Å³

Data collection top

Bruker APEXII CCD diffractometer	5470 independent reflections
Radiation source: fine-focus sealed tube	4786 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 7.50 pixels mm^-1	θ_max = 28.3°, θ_min = 2.1°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
T_min = 0.514, T_max = 0.593	l = −16→16
18376 measured reflections

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.049	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0194P)² + 0.3314P] where P = (F_o² + 2F_c²)/3
5470 reflections	(Δ/σ)_max = 0.002
250 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Sn₄(CH₃)₈(C₈H₇O₂)₄O₂]	γ = 71.876 (1)°
M_r = 1167.66	V = 1116.24 (4) Å³
Triclinic, P1	Z = 1
a = 10.0413 (2) Å	Mo Kα radiation
b = 10.1280 (2) Å	µ = 2.26 mm⁻¹
c = 12.0910 (3) Å	T = 296 K
α = 83.300 (1)°	0.30 × 0.26 × 0.23 mm
β = 72.850 (2)°

Data collection top

Bruker APEXII CCD diffractometer	5470 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4786 reflections with I > 2σ(I)
T_min = 0.514, T_max = 0.593	R_int = 0.024
18376 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	0 restraints
wR(F²) = 0.049	H-atom parameters constrained
S = 1.09	Δρ_max = 0.43 e Å⁻³
5470 reflections	Δρ_min = −0.40 e Å⁻³
250 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Sn1	0.22041 (1)	0.28397 (1)	0.53408 (1)	0.0339 (1)
Sn2	0.57013 (1)	0.05882 (1)	0.58448 (1)	0.0328 (1)
O1	0.26212 (16)	0.33067 (15)	0.69668 (12)	0.0441 (5)
O2	0.50311 (16)	0.27701 (15)	0.64565 (14)	0.0488 (5)
O3	0.39865 (14)	0.11621 (13)	0.51399 (12)	0.0374 (4)
O4	0.20722 (17)	0.18882 (15)	0.38766 (13)	0.0474 (5)
O5	0.0386 (2)	0.38219 (17)	0.36273 (15)	0.0601 (6)
C1	0.3791 (2)	0.3503 (2)	0.69953 (17)	0.0364 (6)
C2	0.3696 (2)	0.46856 (19)	0.76660 (16)	0.0341 (6)
C3	0.2507 (2)	0.5860 (2)	0.77069 (19)	0.0432 (7)
C4	0.2381 (3)	0.7032 (2)	0.8260 (2)	0.0497 (7)
C5	0.3430 (3)	0.7029 (2)	0.8776 (2)	0.0495 (7)
C6	0.4602 (3)	0.5859 (2)	0.87427 (19)	0.0462 (7)
C7	0.4771 (2)	0.4666 (2)	0.81952 (17)	0.0376 (6)
C8	0.6062 (3)	0.3421 (2)	0.8215 (2)	0.0528 (8)
C9	0.0303 (2)	0.2487 (3)	0.6466 (2)	0.0514 (8)
C10	0.2897 (3)	0.4523 (2)	0.4481 (2)	0.0565 (8)
C11	0.7553 (3)	0.1127 (2)	0.4805 (2)	0.0510 (8)
C12	0.4894 (3)	−0.0106 (3)	0.7538 (2)	0.0572 (8)
C13	0.1215 (2)	0.2684 (2)	0.32976 (18)	0.0423 (7)
C14	0.1306 (2)	0.2099 (2)	0.21784 (18)	0.0415 (6)
C15	0.1326 (3)	0.0718 (2)	0.2182 (2)	0.0503 (7)
C16	0.1385 (3)	0.0126 (3)	0.1193 (2)	0.0597 (9)
C17	0.1461 (3)	0.0905 (3)	0.0183 (2)	0.0656 (10)
C18	0.1470 (3)	0.2263 (3)	0.0163 (2)	0.0603 (9)
C19	0.1369 (2)	0.2902 (3)	0.11569 (19)	0.0477 (7)
C20	0.1334 (3)	0.4405 (3)	0.1102 (3)	0.0668 (10)
H3	0.17942	0.58560	0.73612	0.0518*
H4	0.15890	0.78179	0.82819	0.0596*
H5	0.33508	0.78146	0.91482	0.0594*
H6	0.53017	0.58723	0.90992	0.0555*
H8A	0.66157	0.36151	0.86691	0.0792*
H8B	0.66647	0.32205	0.74390	0.0792*
H8C	0.57295	0.26342	0.85508	0.0792*
H9A	0.05583	0.17731	0.70272	0.0771*
H9B	−0.02124	0.21985	0.60307	0.0771*
H9C	−0.03061	0.33286	0.68556	0.0771*
H10A	0.30365	0.44761	0.36649	0.0847*
H10B	0.38001	0.44916	0.46205	0.0847*
H10C	0.21741	0.53757	0.47635	0.0847*
H11A	0.73019	0.17370	0.41799	0.0764*
H11B	0.83035	0.03018	0.44956	0.0764*
H11C	0.78978	0.15895	0.52634	0.0764*
H12A	0.54898	−0.00324	0.80065	0.0858*
H12B	0.49124	−0.10588	0.75313	0.0858*
H12C	0.39110	0.04533	0.78523	0.0858*
H15	0.12990	0.01860	0.28650	0.0604*
H16	0.13734	−0.07909	0.12108	0.0716*
H17	0.15067	0.05150	−0.04918	0.0787*
H18	0.15457	0.27700	−0.05339	0.0724*
H20A	0.19466	0.45179	0.15394	0.1002*
H20B	0.03524	0.49670	0.14206	0.1002*
H20C	0.16794	0.46896	0.03100	0.1002*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0307 (1)	0.0301 (1)	0.0392 (1)	−0.0034 (1)	−0.0120 (1)	−0.0034 (1)
Sn2	0.0304 (1)	0.0345 (1)	0.0344 (1)	−0.0063 (1)	−0.0115 (1)	−0.0060 (1)
O1	0.0397 (8)	0.0516 (9)	0.0440 (8)	−0.0135 (7)	−0.0113 (6)	−0.0126 (7)
O2	0.0406 (8)	0.0430 (8)	0.0617 (10)	−0.0078 (6)	−0.0088 (7)	−0.0237 (7)
O3	0.0355 (7)	0.0316 (6)	0.0467 (8)	−0.0004 (5)	−0.0203 (6)	−0.0099 (6)
O4	0.0507 (9)	0.0438 (8)	0.0483 (9)	0.0001 (7)	−0.0264 (7)	−0.0083 (6)
O5	0.0612 (11)	0.0534 (10)	0.0574 (10)	0.0092 (8)	−0.0259 (8)	−0.0158 (8)
C1	0.0383 (10)	0.0380 (10)	0.0323 (10)	−0.0095 (8)	−0.0095 (8)	−0.0038 (8)
C2	0.0351 (10)	0.0324 (9)	0.0333 (10)	−0.0083 (8)	−0.0074 (7)	−0.0047 (7)
C3	0.0392 (11)	0.0399 (11)	0.0470 (12)	−0.0030 (9)	−0.0133 (9)	−0.0076 (9)
C4	0.0497 (13)	0.0345 (10)	0.0544 (14)	0.0006 (9)	−0.0096 (10)	−0.0084 (9)
C5	0.0609 (14)	0.0365 (11)	0.0484 (13)	−0.0140 (10)	−0.0070 (10)	−0.0126 (9)
C6	0.0482 (12)	0.0490 (12)	0.0455 (12)	−0.0154 (10)	−0.0138 (9)	−0.0109 (9)
C7	0.0379 (10)	0.0366 (10)	0.0361 (10)	−0.0080 (8)	−0.0080 (8)	−0.0061 (8)
C8	0.0499 (13)	0.0507 (13)	0.0588 (14)	−0.0017 (10)	−0.0263 (11)	−0.0115 (11)
C9	0.0386 (12)	0.0555 (13)	0.0587 (14)	−0.0151 (10)	−0.0073 (10)	−0.0082 (11)
C10	0.0666 (16)	0.0438 (12)	0.0581 (15)	−0.0186 (11)	−0.0158 (12)	0.0060 (10)
C11	0.0465 (13)	0.0465 (12)	0.0556 (14)	−0.0168 (10)	−0.0036 (10)	−0.0028 (10)
C12	0.0550 (14)	0.0631 (15)	0.0442 (13)	−0.0122 (12)	−0.0058 (10)	0.0005 (11)
C13	0.0404 (11)	0.0436 (11)	0.0436 (12)	−0.0074 (9)	−0.0160 (9)	−0.0051 (9)
C14	0.0344 (10)	0.0462 (11)	0.0417 (11)	−0.0025 (9)	−0.0147 (8)	−0.0072 (9)
C15	0.0517 (13)	0.0475 (12)	0.0502 (13)	−0.0039 (10)	−0.0215 (10)	−0.0051 (10)
C16	0.0617 (16)	0.0532 (14)	0.0621 (16)	−0.0041 (12)	−0.0204 (12)	−0.0199 (12)
C17	0.0602 (16)	0.0784 (19)	0.0527 (15)	−0.0040 (14)	−0.0143 (12)	−0.0287 (14)
C18	0.0558 (15)	0.0817 (19)	0.0375 (12)	−0.0121 (13)	−0.0120 (10)	−0.0026 (12)
C19	0.0395 (11)	0.0577 (13)	0.0439 (12)	−0.0092 (10)	−0.0132 (9)	−0.0031 (10)
C20	0.0742 (18)	0.0673 (17)	0.0639 (17)	−0.0287 (14)	−0.0237 (14)	0.0143 (13)

Geometric parameters (Å, º) top

Sn1—O1	2.2561 (15)	C18—C19	1.394 (3)
Sn1—O3	2.0241 (14)	C19—C20	1.506 (4)
Sn1—O4	2.1671 (16)	C3—H3	0.9300
Sn1—C9	2.098 (2)	C4—H4	0.9300
Sn1—C10	2.090 (2)	C5—H5	0.9300
Sn2—O2	2.2463 (15)	C6—H6	0.9300
Sn2—O3	2.0387 (15)	C8—H8A	0.9600
Sn2—C11	2.104 (3)	C8—H8B	0.9600
Sn2—C12	2.094 (2)	C8—H8C	0.9600
Sn2—Sn2ⁱ	3.2993 (2)	C9—H9A	0.9600
Sn2—O3ⁱ	2.1412 (13)	C9—H9B	0.9600
O1—C1	1.261 (3)	C9—H9C	0.9600
O2—C1	1.259 (3)	C10—H10A	0.9600
O4—C13	1.293 (3)	C10—H10B	0.9600
O5—C13	1.223 (3)	C10—H10C	0.9600
C1—C2	1.487 (3)	C11—H11A	0.9600
C2—C3	1.392 (3)	C11—H11B	0.9600
C2—C7	1.402 (3)	C11—H11C	0.9600
C3—C4	1.384 (3)	C12—H12A	0.9600
C4—C5	1.373 (4)	C12—H12B	0.9600
C5—C6	1.381 (3)	C12—H12C	0.9600
C6—C7	1.386 (3)	C15—H15	0.9300
C7—C8	1.505 (3)	C16—H16	0.9300
C13—C14	1.507 (3)	C17—H17	0.9300
C14—C15	1.392 (3)	C18—H18	0.9300
C14—C19	1.394 (3)	C20—H20A	0.9600
C15—C16	1.377 (3)	C20—H20B	0.9600
C16—C17	1.370 (4)	C20—H20C	0.9600
C17—C18	1.376 (4)

Sn1···O5ⁱⁱ	3.6541 (17)	C1···H8C	2.9700
Sn2···C13ⁱ	4.045 (2)	C1···H10B	2.9300
Sn1···H11Bⁱ	3.3500	C1···H8B	3.0100
Sn2···H15ⁱ	3.6200	C3···H20Bⁱⁱ	3.0900
O1···Sn2	3.4765 (15)	C4···H11A^iv	3.0300
O1···O3	2.9929 (19)	C5···H8Aⁱⁱⁱ	3.0700
O1···C9	2.937 (3)	C5···H12B^v	2.8300
O1···C10	3.080 (3)	C6···H8Aⁱⁱⁱ	3.0500
O2···C8	2.842 (3)	C6···H6ⁱⁱⁱ	2.9800
O2···Sn1	3.4633 (17)	C7···H10A^iv	2.9100
O2···O3	2.990 (2)	C8···H10A^iv	3.0600
O2···C11	2.888 (3)	C9···H11Bⁱ	2.9400
O2···C12	3.077 (3)	C10···H8B^iv	3.1000
O3···O3ⁱ	2.5685 (19)	C13···H10A	3.0900
O3···C10	3.314 (2)	C13···H20A	2.7400
O3···C12	3.294 (3)	C14···H4ⁱⁱ	3.0900
O3···O4	2.676 (2)	C14···H3ⁱⁱ	3.0900
O3···O1	2.9929 (19)	C15···H4ⁱⁱ	3.0300
O3···O2	2.990 (2)	C15···H12Aⁱ	3.0000
O3···C12ⁱ	3.287 (3)	C16···H4ⁱⁱ	3.0000
O3···C1	3.374 (2)	C17···H4ⁱⁱ	3.0400
O3···C11ⁱ	3.147 (3)	C19···H3ⁱⁱ	3.0900
O4···Sn2ⁱ	2.8567 (16)	H3···O1	2.5100
O4···O3	2.676 (2)	H3···O5ⁱⁱ	2.7100
O4···C10	3.245 (3)	H3···C14ⁱⁱ	3.0900
O4···C11ⁱ	3.243 (2)	H3···C19ⁱⁱ	3.0900
O4···C9	3.134 (3)	H3···H20Bⁱⁱ	2.5400
O4···C12ⁱ	3.113 (3)	H4···C14ⁱⁱ	3.0900
O5···C10	3.278 (4)	H4···C15ⁱⁱ	3.0300
O5···Sn1ⁱⁱ	3.6541 (17)	H4···C16ⁱⁱ	3.0000
O5···C20	2.965 (4)	H4···C17ⁱⁱ	3.0400
O1···H3	2.5100	H5···H12B^v	2.5200
O2···H8B	2.4600	H6···H8A	2.2900
O2···H8C	2.8000	H6···C6ⁱⁱⁱ	2.9800
O2···H11C	2.7600	H6···H20A^iv	2.5500
O4···H12Bⁱ	2.9100	H8A···H6	2.2900
O4···H9B	2.8900	H8A···C5ⁱⁱⁱ	3.0700
O4···H11Bⁱ	2.8300	H8A···C6ⁱⁱⁱ	3.0500
O4···H15	2.6400	H8B···O2	2.4600
O5···H20A	2.7000	H8B···C1	3.0100
O5···H20B	2.7900	H8B···C10^iv	3.1000
O5···H3ⁱⁱ	2.7100	H8C···O2	2.8000
O5···H9Cⁱⁱ	2.8600	H8C···C1	2.9700
O5···H10Cⁱⁱ	2.6800	H9B···H11C^vi	2.6000
C3···C19ⁱⁱ	3.581 (3)	H9C···O5ⁱⁱ	2.8600
C6···C6ⁱⁱⁱ	3.499 (3)	H10A···C13	3.0900
C7···C10^iv	3.569 (3)	H10A···C7^iv	2.9100
C8···O2	2.842 (3)	H10A···C8^iv	3.0600
C9···O4	3.134 (3)	H10B···C1	2.9300
C9···O1	2.937 (3)	H10C···O5ⁱⁱ	2.6800
C10···C7^iv	3.569 (3)	H11A···C4^iv	3.0300
C10···C1	3.379 (3)	H11B···Sn1ⁱ	3.3500
C10···O4	3.245 (3)	H11B···O4ⁱ	2.8300
C10···C13	3.518 (3)	H11B···C9ⁱ	2.9400
C10···O5	3.278 (4)	H11C···H9B^vii	2.6000
C10···O3	3.314 (2)	H12A···C15ⁱ	3.0000
C10···O1	3.080 (3)	H12B···C5^viii	2.8300
C11···O2	2.888 (3)	H12B···H5^viii	2.5200
C11···O4ⁱ	3.242 (2)	H12B···O4ⁱ	2.9100
C11···Sn1ⁱ	3.970 (2)	H15···O4	2.6400
C11···O3ⁱ	3.147 (3)	H15···Sn2ⁱ	3.6200
C12···O3ⁱ	3.287 (3)	H18···H20C	2.3500
C12···C1	3.517 (3)	H20A···O5	2.7000
C12···O4ⁱ	3.113 (3)	H20A···C13	2.7400
C12···O3	3.294 (3)	H20A···H6^iv	2.5500
C12···O2	3.077 (3)	H20B···O5	2.7900
C13···Sn2ⁱ	4.044 (2)	H20B···C3ⁱⁱ	3.0900
C19···C3ⁱⁱ	3.581 (3)	H20B···H3ⁱⁱ	2.5400
C20···O5	2.965 (4)	H20C···H18	2.3500

O1—Sn1—O3	88.56 (6)	C14—C19—C20	122.4 (2)
O1—Sn1—O4	166.35 (5)	C18—C19—C20	120.1 (2)
O1—Sn1—C9	84.75 (8)	C2—C3—H3	120.00
O1—Sn1—C10	90.16 (8)	C4—C3—H3	120.00
O3—Sn1—O4	79.26 (6)	C3—C4—H4	120.00
O3—Sn1—C9	114.11 (9)	C5—C4—H4	120.00
O3—Sn1—C10	107.30 (8)	C4—C5—H5	120.00
O4—Sn1—C9	94.55 (8)	C6—C5—H5	120.00
O4—Sn1—C10	99.29 (8)	C5—C6—H6	119.00
C9—Sn1—C10	138.08 (11)	C7—C6—H6	119.00
O2—Sn2—O3	88.35 (6)	C7—C8—H8A	109.00
O2—Sn2—C11	83.12 (7)	C7—C8—H8B	109.00
O2—Sn2—C12	90.24 (9)	C7—C8—H8C	109.00
Sn2ⁱ—Sn2—O2	126.86 (4)	H8A—C8—H8B	109.00
O2—Sn2—O3ⁱ	162.12 (6)	H8A—C8—H8C	109.00
O3—Sn2—C11	113.89 (8)	H8B—C8—H8C	110.00
O3—Sn2—C12	105.70 (10)	Sn1—C9—H9A	109.00
Sn2ⁱ—Sn2—O3	38.99 (4)	Sn1—C9—H9B	109.00
O3—Sn2—O3ⁱ	75.78 (5)	Sn1—C9—H9C	109.00
C11—Sn2—C12	139.56 (11)	H9A—C9—H9B	109.00
Sn2ⁱ—Sn2—C11	108.32 (7)	H9A—C9—H9C	109.00
O3ⁱ—Sn2—C11	95.66 (7)	H9B—C9—H9C	109.00
Sn2ⁱ—Sn2—C12	107.47 (8)	Sn1—C10—H10A	110.00
O3ⁱ—Sn2—C12	101.83 (9)	Sn1—C10—H10B	109.00
Sn2ⁱ—Sn2—O3ⁱ	36.80 (4)	Sn1—C10—H10C	109.00
Sn1—O1—C1	123.85 (13)	H10A—C10—H10B	109.00
Sn2—O2—C1	129.00 (14)	H10A—C10—H10C	109.00
Sn1—O3—Sn2	132.78 (7)	H10B—C10—H10C	109.00
Sn1—O3—Sn2ⁱ	122.76 (7)	Sn2—C11—H11A	109.00
Sn2—O3—Sn2ⁱ	104.22 (6)	Sn2—C11—H11B	110.00
Sn1—O4—C13	115.13 (12)	Sn2—C11—H11C	110.00
O1—C1—O2	123.10 (19)	H11A—C11—H11B	109.00
O1—C1—C2	118.30 (18)	H11A—C11—H11C	109.00
O2—C1—C2	118.57 (19)	H11B—C11—H11C	110.00
C1—C2—C3	116.73 (19)	Sn2—C12—H12A	109.00
C1—C2—C7	122.57 (18)	Sn2—C12—H12B	109.00
C3—C2—C7	120.64 (18)	Sn2—C12—H12C	109.00
C2—C3—C4	120.3 (2)	H12A—C12—H12B	109.00
C3—C4—C5	119.7 (2)	H12A—C12—H12C	110.00
C4—C5—C6	120.0 (2)	H12B—C12—H12C	109.00
C5—C6—C7	122.2 (3)	C14—C15—H15	119.00
C2—C7—C6	117.3 (2)	C16—C15—H15	119.00
C2—C7—C8	123.55 (19)	C15—C16—H16	120.00
C6—C7—C8	119.2 (2)	C17—C16—H16	120.00
O4—C13—O5	123.1 (2)	C16—C17—H17	120.00
O4—C13—C14	114.83 (17)	C18—C17—H17	120.00
O5—C13—C14	122.09 (19)	C17—C18—H18	119.00
C13—C14—C15	118.28 (18)	C19—C18—H18	119.00
C13—C14—C19	121.75 (19)	C19—C20—H20A	110.00
C15—C14—C19	120.0 (2)	C19—C20—H20B	109.00
C14—C15—C16	121.2 (2)	C19—C20—H20C	109.00
C15—C16—C17	119.2 (3)	H20A—C20—H20B	109.00
C16—C17—C18	120.2 (2)	H20A—C20—H20C	109.00
C17—C18—C19	121.9 (2)	H20B—C20—H20C	109.00
C14—C19—C18	117.5 (2)

O3—Sn1—O1—C1	57.73 (15)	C12—Sn2—Sn2ⁱ—C12ⁱ	−180.00 (12)
C9—Sn1—O1—C1	172.10 (17)	O3ⁱ—Sn2—Sn2ⁱ—O3	−179.98 (13)
C10—Sn1—O1—C1	−49.57 (17)	O3—Sn2—O3ⁱ—Sn1ⁱ	174.92 (9)
O1—Sn1—O3—Sn2	−16.38 (10)	O3—Sn2—O3ⁱ—Sn2ⁱ	−0.03 (14)
O1—Sn1—O3—Sn2ⁱ	156.91 (8)	C11—Sn2—O3ⁱ—Sn1ⁱ	61.67 (10)
O4—Sn1—O3—Sn2	169.83 (11)	C11—Sn2—O3ⁱ—Sn2ⁱ	−113.25 (8)
O4—Sn1—O3—Sn2ⁱ	−16.88 (8)	C12—Sn2—O3ⁱ—Sn1ⁱ	−81.66 (12)
C9—Sn1—O3—Sn2	−99.97 (11)	C12—Sn2—O3ⁱ—Sn2ⁱ	103.42 (10)
C9—Sn1—O3—Sn2ⁱ	73.32 (10)	Sn1—O1—C1—O2	−42.7 (3)
C10—Sn1—O3—Sn2	73.34 (12)	Sn1—O1—C1—C2	135.22 (15)
C10—Sn1—O3—Sn2ⁱ	−113.38 (10)	Sn2—O2—C1—O1	−23.7 (3)
O3—Sn1—O4—C13	−163.73 (16)	Sn2—O2—C1—C2	158.41 (13)
C9—Sn1—O4—C13	82.56 (17)	Sn1—O4—C13—O5	−9.5 (3)
C10—Sn1—O4—C13	−57.73 (17)	Sn1—O4—C13—C14	170.80 (14)
O3—Sn2—O2—C1	49.17 (18)	O1—C1—C2—C3	−32.3 (3)
C11—Sn2—O2—C1	163.47 (19)	O1—C1—C2—C7	150.43 (19)
C12—Sn2—O2—C1	−56.53 (19)	O2—C1—C2—C3	145.7 (2)
Sn2ⁱ—Sn2—O2—C1	55.71 (19)	O2—C1—C2—C7	−31.6 (3)
O2—Sn2—O3—Sn1	−14.15 (10)	C1—C2—C3—C4	−176.5 (2)
O2—Sn2—O3—Sn2ⁱ	171.68 (7)	C7—C2—C3—C4	0.8 (3)
C11—Sn2—O3—Sn1	−95.88 (11)	C1—C2—C7—C6	176.54 (19)
C11—Sn2—O3—Sn2ⁱ	89.95 (8)	C1—C2—C7—C8	−4.7 (3)
C12—Sn2—O3—Sn1	75.64 (12)	C3—C2—C7—C6	−0.6 (3)
C12—Sn2—O3—Sn2ⁱ	−98.54 (9)	C3—C2—C7—C8	178.2 (2)
Sn2ⁱ—Sn2—O3—Sn1	174.18 (14)	C2—C3—C4—C5	−0.4 (3)
O3ⁱ—Sn2—O3—Sn1	174.18 (11)	C3—C4—C5—C6	−0.1 (4)
O3ⁱ—Sn2—O3—Sn2ⁱ	0.03 (13)	C4—C5—C6—C7	0.3 (4)
O2—Sn2—Sn2ⁱ—O3	−10.42 (8)	C5—C6—C7—C2	0.1 (3)
O2—Sn2—Sn2ⁱ—O2ⁱ	180.00 (8)	C5—C6—C7—C8	−178.8 (2)
O2—Sn2—Sn2ⁱ—O3ⁱ	169.58 (8)	O4—C13—C14—C15	45.0 (3)
O2—Sn2—Sn2ⁱ—C11ⁱ	−84.82 (8)	O4—C13—C14—C19	−135.0 (2)
O2—Sn2—Sn2ⁱ—C12ⁱ	76.02 (10)	O5—C13—C14—C15	−134.7 (3)
O3—Sn2—Sn2ⁱ—O2ⁱ	−169.58 (8)	O5—C13—C14—C19	45.3 (3)
O3—Sn2—Sn2ⁱ—O3ⁱ	179.98 (13)	C13—C14—C15—C16	179.0 (3)
O3—Sn2—Sn2ⁱ—C11ⁱ	−74.40 (9)	C19—C14—C15—C16	−1.0 (4)
O3—Sn2—Sn2ⁱ—C12ⁱ	86.45 (11)	C13—C14—C19—C18	179.2 (2)
C11—Sn2—Sn2ⁱ—O3	−105.61 (9)	C13—C14—C19—C20	−0.7 (4)
C11—Sn2—Sn2ⁱ—O2ⁱ	84.81 (8)	C15—C14—C19—C18	−0.8 (4)
C11—Sn2—Sn2ⁱ—O3ⁱ	74.39 (9)	C15—C14—C19—C20	179.3 (3)
C11—Sn2—Sn2ⁱ—C11ⁱ	180.00 (9)	C14—C15—C16—C17	1.6 (5)
C11—Sn2—Sn2ⁱ—C12ⁱ	−19.16 (11)	C15—C16—C17—C18	−0.4 (5)
C12—Sn2—Sn2ⁱ—O3	93.56 (11)	C16—C17—C18—C19	−1.5 (5)
C12—Sn2—Sn2ⁱ—O2ⁱ	−76.02 (10)	C17—C18—C19—C14	2.1 (4)
C12—Sn2—Sn2ⁱ—O3ⁱ	−86.45 (11)	C17—C18—C19—C20	−178.0 (3)
C12—Sn2—Sn2ⁱ—C11ⁱ	19.16 (11)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x+1, −y+1, −z+1; (v) x, y+1, z; (vi) x−1, y, z; (vii) x+1, y, z; (viii) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C14–C19 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···O5ⁱⁱ	0.96	2.678	3.452 (3)	138
C4—H4···Cgⁱⁱ	0.93	2.74	3.493 (3)	139

Symmetry code: (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Sn₄(CH₃)₈(C₈H₇O₂)₄O₂]
M_r	1167.66
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.0413 (2), 10.1280 (2), 12.0910 (3)
α, β, γ (°)	83.300 (1), 72.850 (2), 71.876 (1)
V (Å³)	1116.24 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.26
Crystal size (mm)	0.30 × 0.26 × 0.23

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.514, 0.593
No. of measured, independent and observed [I > 2σ(I)] reflections	18376, 5470, 4786
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.049, 1.09
No. of reflections	5470
No. of parameters	250
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.40

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C14–C19 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···O5ⁱ	0.96	2.678	3.452 (3)	138
C4—H4···Cgⁱ	0.93	2.74	3.493 (3)	139

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Amini, M. M., Abadi, S. H., Mirzaee, M., Lügger, T., Hahn, F. E. & Ng, S. W. (2002). Acta Cryst. E58, m697–m699. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Danish, M., Tahir, M. N., Ahmad, N., Raza, A. R. & Ibrahim, M. (2009). Acta Cryst. E65, m609–m610. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 10| October 2010| Pages m1268-m1269

doi:10.1107/S1600536810036512

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