Diacetatodi-tert-butyltin(IV).

The title compound, [Sn(C4H9)2(CH3COO)2], was synthesized in order to study the influence of large organic groups on the mol-ecular structure of diorganotin di-acetates. The title compound exhibits the same structure type as other diorganotin(IV) di-acetates characterized by an unsymmetrical bidentate bonding mode of the two acetate groups to tin. The influence of the t-butyl groups on this mol-ecular structure is expressed in two significant differences: tin-carbon bond lengths are much more longer than in the other di-acetates, as are the additional inter-actions of the acetate groups with the tin atom. Inter-molecular inter-actions are restricted to C-H⋯O ones similar to those in the other di-acetates, giving rise to a chain-like arrangement of the molecules with the tin atoms and acetate groups in the propagation plane.

Related literature

For background to diorganotin(IV) carboxyl­ates, see: Tiekink (1991 ▶) and to diorganotin(IV) di­acetates, see: Alcock et al. (1992 ▶); Lockhart et al. (1987 ▶); Mistry et al. (1995 ▶).

Experimental

Crystal data

[Sn(C4H9)2(C2H3O2)2]

M = 351.00

Monoclinic,

a = 6.1039 (3) Å

b = 15.3928 (7) Å

c = 15.9601 (8) Å

β = 95.462 (2)°

V = 1492.74 (12) Å3

Z = 4

Mo Kα radiation

μ = 1.71 mm−1

T = 100 K

0.14 × 0.06 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.791, T max = 0.939

76636 measured reflections

3590 independent reflections

2980 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.046

S = 1.04

3590 reflections

167 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.51 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009185/aa2086sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009185/aa2086Isup2.hkl

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

[Sn(C4H9)2(C2H3O2)2]	F(000) = 712
Mr = 351.00	Dx = 1.562 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6480 reflections
a = 6.1039 (3) Å	θ = 2.6–25.7°
b = 15.3928 (7) Å	µ = 1.71 mm−1
c = 15.9601 (8) Å	T = 100 K
β = 95.462 (2)°	Block, colourless
V = 1492.74 (12) Å3	0.14 × 0.06 × 0.04 mm
Z = 4

Bruker APEXII CCD diffractometer	3590 independent reflections
Radiation source: fine-focus sealed tube	2980 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
φ and ω scans	θmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.791, Tmax = 0.939	k = −20→19
76636 measured reflections	l = −21→21

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)] = 0.023	H-atom parameters constrained
wR(F2) = 0.046	w = 1/[σ2(Fo2) + (0.0133P)2 + 1.0511P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.002
3590 reflections	Δρmax = 0.59 e Å−3
167 parameters	Δρmin = −0.51 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00201 (16)

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
Sn1	0.19140 (2)	0.295768 (9)	0.285075 (8)	0.01333 (6)
C11	0.0432 (3)	0.20445 (14)	0.19231 (13)	0.0162 (4)
C12	−0.1709 (3)	0.24192 (16)	0.14968 (14)	0.0257 (5)
H12A	−0.2374	0.2001	0.1085	0.031 (2)*
H12B	−0.1396	0.2962	0.1211	0.031 (2)*
H12C	−0.2730	0.2534	0.1922	0.031 (2)*
C13	0.2095 (4)	0.18975 (15)	0.12781 (13)	0.0216 (5)
H13A	0.3485	0.1689	0.1566	0.031 (2)*
H13B	0.2350	0.2445	0.0990	0.031 (2)*
H13C	0.1515	0.1464	0.0865	0.031 (2)*
C14	−0.0036 (4)	0.11881 (15)	0.23553 (14)	0.0259 (5)
H14A	−0.1128	0.1285	0.2758	0.031 (2)*
H14B	0.1327	0.0966	0.2654	0.031 (2)*
H14C	−0.0609	0.0764	0.1932	0.031 (2)*
C21	0.0894 (3)	0.38924 (14)	0.37595 (12)	0.0161 (4)
C22	−0.0723 (4)	0.34722 (15)	0.43092 (14)	0.0245 (5)
H22A	−0.1180	0.3900	0.4713	0.030 (2)*
H22B	−0.0011	0.2980	0.4614	0.030 (2)*
H22C	−0.2016	0.3267	0.3953	0.030 (2)*
C23	0.2995 (4)	0.41692 (15)	0.42919 (14)	0.0243 (5)
H23A	0.2626	0.4591	0.4717	0.030 (2)*
H23B	0.4014	0.4435	0.3928	0.030 (2)*
H23C	0.3689	0.3659	0.4572	0.030 (2)*
C24	−0.0185 (4)	0.46712 (15)	0.33009 (14)	0.0249 (5)
H24A	−0.1502	0.4481	0.2950	0.030 (2)*
H24B	0.0852	0.4936	0.2944	0.030 (2)*
H24C	−0.0601	0.5098	0.3713	0.030 (2)*
O11	0.4677 (2)	0.22581 (9)	0.33641 (9)	0.0198 (3)
O12	0.1995 (3)	0.18113 (10)	0.40892 (10)	0.0251 (4)
C15	0.3940 (4)	0.17649 (14)	0.39399 (13)	0.0203 (5)
C16	0.5546 (4)	0.11407 (16)	0.43777 (14)	0.0265 (5)
H16A	0.5282	0.1099	0.4973	0.037 (4)*
H16B	0.7049	0.1347	0.4333	0.037 (4)*
H16C	0.5357	0.0567	0.4114	0.037 (4)*
O21	0.4416 (2)	0.36282 (9)	0.23048 (9)	0.0178 (3)
O22	0.1404 (2)	0.41038 (10)	0.15759 (9)	0.0231 (3)
C25	0.3440 (4)	0.40733 (13)	0.16819 (13)	0.0185 (5)
C26	0.4899 (4)	0.45081 (15)	0.11080 (14)	0.0240 (5)
H26A	0.5160	0.4114	0.0646	0.038 (4)*
H26B	0.6306	0.4656	0.1423	0.038 (4)*
H26C	0.4188	0.5039	0.0879	0.038 (4)*

	U11	U22	U33	U12	U13	U23
Sn1	0.01484 (8)	0.01307 (8)	0.01231 (8)	0.00027 (6)	0.00240 (5)	−0.00084 (6)
C11	0.0158 (10)	0.0177 (11)	0.0156 (10)	−0.0010 (8)	0.0038 (8)	−0.0048 (8)
C12	0.0162 (11)	0.0342 (14)	0.0260 (12)	0.0018 (10)	−0.0017 (9)	−0.0072 (10)
C13	0.0222 (11)	0.0235 (13)	0.0194 (11)	−0.0006 (9)	0.0037 (9)	−0.0078 (9)
C14	0.0294 (13)	0.0220 (12)	0.0276 (12)	−0.0095 (10)	0.0089 (10)	−0.0041 (10)
C21	0.0153 (10)	0.0166 (11)	0.0167 (10)	0.0006 (8)	0.0028 (8)	−0.0051 (8)
C22	0.0249 (12)	0.0239 (13)	0.0265 (12)	0.0005 (10)	0.0128 (10)	−0.0036 (10)
C23	0.0246 (12)	0.0266 (13)	0.0216 (12)	−0.0006 (10)	0.0018 (9)	−0.0093 (9)
C24	0.0303 (13)	0.0204 (12)	0.0246 (12)	0.0065 (10)	0.0057 (10)	−0.0020 (9)
O11	0.0211 (8)	0.0180 (8)	0.0199 (8)	0.0020 (6)	−0.0005 (6)	0.0035 (6)
O12	0.0273 (9)	0.0222 (9)	0.0263 (9)	0.0039 (7)	0.0055 (7)	0.0017 (7)
C15	0.0286 (13)	0.0147 (11)	0.0166 (11)	0.0014 (9)	−0.0025 (9)	−0.0031 (8)
C16	0.0337 (13)	0.0229 (12)	0.0221 (12)	0.0072 (10)	−0.0024 (10)	0.0049 (10)
O21	0.0192 (8)	0.0172 (8)	0.0174 (7)	−0.0003 (6)	0.0046 (6)	0.0027 (6)
O22	0.0226 (9)	0.0267 (9)	0.0202 (8)	0.0019 (7)	0.0028 (6)	0.0013 (6)
C25	0.0279 (12)	0.0137 (11)	0.0147 (10)	−0.0021 (9)	0.0055 (9)	−0.0036 (8)
C26	0.0304 (13)	0.0215 (13)	0.0209 (12)	−0.0012 (10)	0.0076 (10)	0.0030 (9)

Sn1—O21	2.1001 (14)	C22—H22B	0.9800
Sn1—O11	2.1002 (14)	C22—H22C	0.9800
Sn1—C11	2.175 (2)	C23—H23A	0.9800
Sn1—C21	2.176 (2)	C23—H23B	0.9800
C11—C14	1.527 (3)	C23—H23C	0.9800
C11—C12	1.528 (3)	C24—H24A	0.9800
C11—C13	1.530 (3)	C24—H24B	0.9800
C12—H12A	0.9800	C24—H24C	0.9800
C12—H12B	0.9800	O11—C15	1.304 (3)
C12—H12C	0.9800	O12—C15	1.235 (3)
C13—H13A	0.9800	C15—C16	1.497 (3)
C13—H13B	0.9800	C16—H16A	0.9800
C13—H13C	0.9800	C16—H16B	0.9800
C14—H14A	0.9800	C16—H16C	0.9800
C14—H14B	0.9800	O21—C25	1.304 (3)
C14—H14C	0.9800	O22—C25	1.239 (3)
C21—C24	1.522 (3)	C25—C26	1.495 (3)
C21—C22	1.525 (3)	C26—H26A	0.9800
C21—C23	1.530 (3)	C26—H26B	0.9800
C22—H22A	0.9800	C26—H26C	0.9800
O21—Sn1—O11	79.93 (6)	C21—C22—H22B	109.5
O21—Sn1—C11	107.88 (7)	H22A—C22—H22B	109.5
O11—Sn1—C11	101.58 (7)	C21—C22—H22C	109.5
O21—Sn1—C21	102.54 (7)	H22A—C22—H22C	109.5
O11—Sn1—C21	110.43 (7)	H22B—C22—H22C	109.5
C11—Sn1—C21	138.97 (7)	C21—C23—H23A	109.5
C14—C11—C12	109.77 (18)	C21—C23—H23B	109.5
C14—C11—C13	109.93 (18)	H23A—C23—H23B	109.5
C12—C11—C13	110.51 (17)	C21—C23—H23C	109.5
C14—C11—Sn1	109.51 (14)	H23A—C23—H23C	109.5
C12—C11—Sn1	109.99 (14)	H23B—C23—H23C	109.5
C13—C11—Sn1	107.09 (13)	C21—C24—H24A	109.5
C11—C12—H12A	109.5	C21—C24—H24B	109.5
C11—C12—H12B	109.5	H24A—C24—H24B	109.5
H12A—C12—H12B	109.5	C21—C24—H24C	109.5
C11—C12—H12C	109.5	H24A—C24—H24C	109.5
H12A—C12—H12C	109.5	H24B—C24—H24C	109.5
H12B—C12—H12C	109.5	C15—O11—Sn1	104.81 (13)
C11—C13—H13A	109.5	O12—C15—O11	120.3 (2)
C11—C13—H13B	109.5	O12—C15—C16	123.1 (2)
H13A—C13—H13B	109.5	O11—C15—C16	116.6 (2)
C11—C13—H13C	109.5	C15—C16—H16A	109.5
H13A—C13—H13C	109.5	C15—C16—H16B	109.5
H13B—C13—H13C	109.5	H16A—C16—H16B	109.5
C11—C14—H14A	109.5	C15—C16—H16C	109.5
C11—C14—H14B	109.5	H16A—C16—H16C	109.5
H14A—C14—H14B	109.5	H16B—C16—H16C	109.5
C11—C14—H14C	109.5	C25—O21—Sn1	106.07 (13)
H14A—C14—H14C	109.5	O22—C25—O21	120.25 (19)
H14B—C14—H14C	109.5	O22—C25—C26	123.21 (19)
C24—C21—C22	109.65 (17)	O21—C25—C26	116.51 (19)
C24—C21—C23	110.46 (18)	C25—C26—H26A	109.5
C22—C21—C23	110.65 (17)	C25—C26—H26B	109.5
C24—C21—Sn1	109.79 (13)	H26A—C26—H26B	109.5
C22—C21—Sn1	110.17 (14)	C25—C26—H26C	109.5
C23—C21—Sn1	106.07 (13)	H26A—C26—H26C	109.5
C21—C22—H22A	109.5	H26B—C26—H26C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···O21i	0.98	2.54	3.362 (3)	142
C22—H22C···O11i	0.98	2.65	3.584 (3)	160
C16—H16C···O22ii	0.98	2.69	3.636 (3)	163
C16—H16A···O22iii	0.98	2.60	3.518 (3)	155

Table 1

Selected bond lengths (Å)

Sn1—O21	2.1001 (14)
Sn1—O11	2.1002 (14)
Sn1—C11	2.175 (2)
Sn1—C21	2.176 (2)
O11—C15	1.304 (3)
O12—C15	1.235 (3)
O21—C25	1.304 (3)
O22—C25	1.239 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12C⋯O21i	0.98	2.54	3.362 (3)	142
C22—H22C⋯O11i	0.98	2.65	3.584 (3)	160
C16—H16C⋯O22ii	0.98	2.69	3.636 (3)	163
C16—H16A⋯O22iii	0.98	2.60	3.518 (3)	155

Symmetry codes: (i) ; (ii) ; (iii) .