catena-Poly[[di-tert-butyl-tin(IV)]-μ-oxalato].

The title compound, [Sn(C4H9)2(C2O4)] n , an unexpected side product in the reaction of di-tert-butyl-tin(IV) oxide with nitric acid, represents the first diorganotin(IV) oxalate to be structurally characterized. The Sn(IV) atom of the one-dimensional coordination polymer is located on a mirror plane and is coordinated by two chelating oxalate ions with two rather different Sn-O bond lengths of 2.150 (1) and 2.425 (1) Å, and two t-butyl groups with Sn-C bond lengths of 2.186 (2) and 2.190 (2) Å. The coordination polyhedron around the Sn(IV) atom is a distorted tetra-gonal disphenoid. The centrosymmetric oxalate ion also has an asymmetric coordination geometry, as reflected by the two slightly different C-O bond lengths of 1.242 (2) and 1.269 (2) Å. The chains of the polymer propagate along the b-axis direction. Only van der Waals inter-actions are observed between the chains.

Related literature

For tin(II) oxalate and related compounds, see: Christie et al. (1979 ▶); Gleizes & Galy (1979 ▶); Ramaswamy et al. (2008 ▶). For (R 3Sn)2Ox (Ox = oxalate) and related compounds, see: Diop et al. (2003 ▶); Ng & Kumar Das (1993 ▶); Ng et al. (1994 ▶); Diop et al. (1997 ▶). For comparative compounds, see: Reichelt & Reuter (2013 ▶).

Experimental

Crystal data

[Sn(C4H9)2(C2O4)]

M = 320.93

Orthorhombic,

a = 11.5763 (3) Å

b = 11.3417 (3) Å

c = 9.3160 (2) Å

V = 1223.14 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.08 mm−1

T = 100 K

0.19 × 0.09 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.691, T max = 0.843

49069 measured reflections

1548 independent reflections

1426 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.015

wR(F 2) = 0.038

S = 1.10

1548 reflections

83 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.37 e Å−3

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: DIAMOND (Brandenburg, 2006 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681400539X/cq2010sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400539X/cq2010Isup2.hkl

CCDC reference: 990826

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Sn(C4H9)2(C2O4)]	F(000) = 640
Mr = 320.93	Dx = 1.743 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 9773 reflections
a = 11.5763 (3) Å	θ = 2.8–29.0°
b = 11.3417 (3) Å	µ = 2.08 mm−1
c = 9.3160 (2) Å	T = 100 K
V = 1223.14 (5) Å3	Needle, colourless
Z = 4	0.19 × 0.09 × 0.09 mm

Bruker APEXII CCD diffractometer	1548 independent reflections
Radiation source: fine-focus sealed tube	1426 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
φ and ω scans	θmax = 28.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.691, Tmax = 0.843	k = −14→14
49069 measured reflections	l = −12→12

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)] = 0.015	H-atom parameters constrained
wR(F2) = 0.038	w = 1/[σ2(Fo2) + (0.0134P)2 + 0.5948P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
1548 reflections	Δρmax = 0.53 e Å−3
83 parameters	Δρmin = −0.37 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (3)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Sn1	0.071797 (12)	0.7500	0.025488 (15)	0.01094 (6)
C1	0.06018 (13)	0.47568 (15)	0.02020 (16)	0.0128 (3)
O1	0.13768 (10)	0.54788 (9)	0.04776 (11)	0.0150 (2)
O2	0.07125 (9)	0.36437 (10)	0.02238 (12)	0.0144 (2)
C11	0.17351 (18)	0.7500	−0.1723 (2)	0.0146 (4)
C12	0.3005 (2)	0.7500	−0.1283 (3)	0.0286 (6)
H12A	0.3488	0.7643	−0.2130	0.0266 (19)*	0.50
H12B	0.3204	0.6734	−0.0864	0.0266 (19)*	0.50
H12C	0.3139	0.8123	−0.0574	0.0266 (19)*	0.50
C13	0.14660 (16)	0.85947 (14)	−0.26272 (18)	0.0231 (3)
H13A	0.1691	0.9304	−0.2096	0.0266 (19)*
H13B	0.0636	0.8622	−0.2834	0.0266 (19)*
H13C	0.1899	0.8558	−0.3530	0.0266 (19)*
C21	0.08213 (18)	0.7500	0.2603 (2)	0.0150 (4)
C22	0.02448 (15)	0.64021 (14)	0.32317 (18)	0.0207 (3)
H22A	0.0662	0.5697	0.2914	0.0266 (19)*
H22B	−0.0558	0.6360	0.2902	0.0266 (19)*
H22C	0.0261	0.6445	0.4282	0.0266 (19)*
C23	0.2108 (2)	0.7500	0.2959 (3)	0.0235 (5)
H23A	0.2211	0.7605	0.3995	0.0266 (19)*	0.50
H23B	0.2489	0.8147	0.2448	0.0266 (19)*	0.50
H23C	0.2450	0.6748	0.2663	0.0266 (19)*	0.50

	U11	U22	U33	U12	U13	U23
Sn1	0.01011 (9)	0.01186 (9)	0.01084 (9)	0.000	−0.00048 (5)	0.000
C1	0.0131 (8)	0.0157 (7)	0.0098 (7)	0.0009 (6)	0.0006 (5)	0.0000 (5)
O1	0.0130 (5)	0.0135 (5)	0.0184 (6)	−0.0008 (4)	−0.0020 (4)	0.0001 (4)
O2	0.0123 (6)	0.0127 (5)	0.0183 (6)	0.0006 (4)	−0.0011 (4)	0.0002 (4)
C11	0.0123 (10)	0.0180 (10)	0.0137 (10)	0.000	0.0020 (8)	0.000
C12	0.0156 (12)	0.0475 (16)	0.0228 (13)	0.000	0.0036 (10)	0.000
C13	0.0303 (9)	0.0211 (8)	0.0178 (8)	0.0007 (7)	0.0064 (7)	0.0036 (6)
C21	0.0130 (10)	0.0217 (10)	0.0103 (10)	0.000	−0.0010 (8)	0.000
C22	0.0224 (8)	0.0237 (8)	0.0159 (8)	−0.0013 (7)	0.0003 (6)	0.0031 (6)
C23	0.0142 (11)	0.0385 (13)	0.0177 (11)	0.000	−0.0034 (9)	0.000

Sn1—O2i	2.150 (1)	C12—H12B	0.9800
Sn1—O2ii	2.150 (1)	C12—H12C	0.9800
Sn1—C11	2.186 (2)	C13—H13A	0.9800
Sn1—C21	2.190 (2)	C13—H13B	0.9800
Sn1—O1	2.425 (1)	C13—H13C	0.9800
Sn1—O1iii	2.425 (1)	C21—C23	1.526 (3)
C1—O1	1.2416 (19)	C21—C22iii	1.530 (2)
C1—O2	1.269 (2)	C21—C22	1.530 (2)
C1—C1i	1.545 (3)	C22—H22A	0.9800
O2—Sn1i	2.1503 (11)	C22—H22B	0.9800
C11—C12	1.526 (3)	C22—H22C	0.9800
C11—C13	1.533 (2)	C23—H23A	0.9800
C11—C13iii	1.533 (2)	C23—H23B	0.9800
C12—H12A	0.9800	C23—H23C	0.9800
O2i—Sn1—O2ii	74.21 (6)	H12A—C12—H12B	109.5
O2i—Sn1—C11	103.89 (5)	C11—C12—H12C	109.5
O2ii—Sn1—C11	103.89 (5)	H12A—C12—H12C	109.5
O2i—Sn1—C21	104.43 (5)	H12B—C12—H12C	109.5
O2ii—Sn1—C21	104.43 (5)	C11—C13—H13A	109.5
C11—Sn1—C21	144.29 (8)	C11—C13—H13B	109.5
O2i—Sn1—O1	71.92 (4)	H13A—C13—H13B	109.5
O2ii—Sn1—O1	146.13 (4)	C11—C13—H13C	109.5
C11—Sn1—O1	84.42 (3)	H13A—C13—H13C	109.5
C21—Sn1—O1	84.11 (3)	H13B—C13—H13C	109.5
O2i—Sn1—O1iii	146.13 (4)	C23—C21—C22iii	110.0 (1)
O2ii—Sn1—O1iii	71.92 (4)	C23—C21—C22	110.0 (1)
C11—Sn1—O1iii	84.42 (3)	C22iii—C21—C22	109.0 (2)
C21—Sn1—O1iii	84.11 (3)	C23—C21—Sn1	105.7 (1)
O1—Sn1—O1iii	141.95 (5)	C22iii—C21—Sn1	111.0 (1)
O1—C1—O2	125.4 (1)	C22—C21—Sn1	111.0 (1)
O1—C1—C1i	117.8 (2)	C21—C22—H22A	109.5
O2—C1—C1i	116.8 (2)	C21—C22—H22B	109.5
C1—O1—Sn1	112.3 (1)	H22A—C22—H22B	109.5
C1—O2—Sn1i	121.3 (1)	C21—C22—H22C	109.5
C12—C11—C13	110.1 (1)	H22A—C22—H22C	109.5
C12—C11—C13iii	110.1 (1)	H22B—C22—H22C	109.5
C13—C11—C13iii	108.2 (2)	C21—C23—H23A	109.5
C12—C11—Sn1	107.0 (2)	C21—C23—H23B	109.5
C13—C11—Sn1	110.7 (1)	H23A—C23—H23B	109.5
C13iii—C11—Sn1	110.7 (1)	C21—C23—H23C	109.5
C11—C12—H12A	109.5	H23A—C23—H23C	109.5
C11—C12—H12B	109.5	H23B—C23—H23C	109.5