1,1'-Di-tert-butyl-2,2',3,3',4,4',5,5'-octa-ethyl-1,1'-bis-tannole.

The title compound, [Sn(2)(C(4)H(9))(2)(C(12)H(20))(2)], has two 1-stannacyclo-penta-diene skeletons related by inversion symmetry located at the mid-point of the Sn-Sn bond [2.7682 (2) Å]. Thus, the asymmetric unit comprises one half-mol-ecule. The planarity of the stannacyclo-penta-diene ring is illustrated by the dihedral angle of 0.3 (1)°, defined by the C(4) and C-Sn-C planes. To avoid steric repulsion, the two stannole rings are oriented in an anti fashion through the Sn-Sn bond. These structural features are similar to those of other bis-tannoles.

Related literature

For the synthesis and X-ray diffraction analysis of bi(1,1-stannole)s whose carbon atoms of the five-membered rings have phenyl groups, see: Saito et al. (2002 ▶, 2005 ▶). For related literature on bi-, oligo- and poly-(1,1-metallole)s, see: Haga et al. (2008 ▶); Kanno et al. (1998 ▶); Kim & Woo (2002 ▶); Saito & Yoshioka (2005 ▶); Saito et al. (2010 ▶); Sohn et al. (1999 ▶, 2003 ▶); Yamaguchi & Tamao (1998 ▶); Yamaguchi et al. (1997 ▶, 1999 ▶).

Experimental

Crystal data

[Sn2(C4H9)2(C12H20)2]

M = 680.20

Monoclinic,

a = 8.7161 (5) Å

b = 16.5999 (9) Å

c = 11.7913 (6) Å

β = 100.827 (1)°

V = 1675.67 (16) Å3

Z = 2

Mo Kα radiation

μ = 1.51 mm−1

T = 100 K

0.25 × 0.10 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (XPREP; Bruker, 2008 ▶) T min = 0.835, T max = 0.927

9015 measured reflections

3636 independent reflections

3387 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.017

wR(F 2) = 0.043

S = 1.04

3636 reflections

161 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XSHELL (Bruker, 2008) ▶; software used to prepare material for publication: XCIF (Bruker, 2008) ▶.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811022951/kp2332sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022951/kp2332Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811022951/kp2332Isup3.cml

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

[Sn2(C4H9)2(C12H20)2]	F(000) = 700
Mr = 680.20	Dx = 1.348 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6469 reflections
a = 8.7161 (5) Å	θ = 2.5–28.1°
b = 16.5999 (9) Å	µ = 1.51 mm−1
c = 11.7913 (6) Å	T = 100 K
β = 100.827 (1)°	Cube, colourless
V = 1675.67 (16) Å3	0.25 × 0.10 × 0.05 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	3636 independent reflections
Radiation source: Bruker TXS fine-focus rotating anode	3387 reflections with I > 2σ(I)
Bruker Helios multilayer confocal mirror	Rint = 0.017
Detector resolution: 8.333 pixels mm-1	θmax = 27.0°, θmin = 2.1°
φ and ω scans	h = −11→9
Absorption correction: multi-scan (XPREP; Bruker, 2008)	k = −21→21
Tmin = 0.835, Tmax = 0.927	l = −14→12
9015 measured reflections

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)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.043	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.020P)2 + 0.7365P] where P = (Fo2 + 2Fc2)/3
3636 reflections	(Δ/σ)max = 0.002
161 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

Experimental. (SADABS; Bruker, 2008)

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	0.025172 (11)	0.980800 (6)	0.390739 (8)	0.01472 (4)
C1	0.08418 (18)	1.07858 (9)	0.28847 (13)	0.0166 (3)
C2	−0.03317 (18)	1.08829 (9)	0.19728 (13)	0.0165 (3)
C3	−0.17491 (18)	1.03462 (9)	0.18331 (13)	0.0166 (3)
C4	−0.18366 (18)	0.97554 (9)	0.26111 (14)	0.0174 (3)
C5	0.20071 (18)	0.88519 (10)	0.40268 (14)	0.0207 (3)
C6	0.2344 (3)	0.86861 (15)	0.28284 (18)	0.0494 (6)
H6A	0.2631	0.9179	0.2498	0.074*
H6B	0.1428	0.8468	0.2347	0.074*
H6C	0.3187	0.8307	0.2884	0.074*
C7	0.3492 (2)	0.91665 (13)	0.47898 (19)	0.0412 (5)
H7A	0.4319	0.8783	0.4801	0.062*
H7B	0.3311	0.9245	0.5560	0.062*
H7C	0.3781	0.9670	0.4489	0.062*
C8	0.1474 (3)	0.80959 (13)	0.4556 (3)	0.0577 (7)
H8A	0.0592	0.7872	0.4042	0.087*
H8B	0.1182	0.8226	0.5280	0.087*
H8C	0.2310	0.7710	0.4681	0.087*
C9	0.23347 (19)	1.12690 (10)	0.31206 (14)	0.0207 (3)
H9A	0.2443	1.1562	0.2428	0.025*
H9B	0.3215	1.0904	0.3308	0.025*
C10	0.2376 (2)	1.18665 (11)	0.41124 (15)	0.0285 (4)
H10A	0.1539	1.2247	0.3915	0.043*
H10B	0.3356	1.2147	0.4246	0.043*
H10C	0.2260	1.1581	0.4799	0.043*
C11	−0.02473 (19)	1.15157 (10)	0.10545 (13)	0.0213 (3)
H11A	0.0349	1.1974	0.1409	0.026*
H11B	−0.1294	1.1701	0.0735	0.026*
C12	0.0514 (2)	1.11894 (11)	0.00763 (14)	0.0276 (4)
H12A	0.1557	1.1013	0.0387	0.041*
H12B	0.0547	1.1607	−0.0482	0.041*
H12C	−0.0086	1.0744	−0.0289	0.041*
C13	−0.30873 (19)	1.05102 (10)	0.08346 (14)	0.0229 (3)
H13A	−0.3647	1.0012	0.0615	0.027*
H13B	−0.2668	1.0698	0.0176	0.027*
C14	−0.4225 (2)	1.11386 (11)	0.11409 (18)	0.0348 (4)
H14A	−0.4702	1.0938	0.1755	0.052*
H14B	−0.5018	1.1246	0.0475	0.052*
H14C	−0.3669	1.1627	0.1385	0.052*
C15	−0.32148 (19)	0.92105 (10)	0.26192 (15)	0.0230 (3)
H15A	−0.4082	0.9395	0.2037	0.028*
H15B	−0.3527	0.9253	0.3364	0.028*
C16	−0.2897 (2)	0.83329 (11)	0.23913 (18)	0.0337 (4)
H16A	−0.2663	0.8279	0.1631	0.051*
H16B	−0.3802	0.8017	0.2446	0.051*
H16C	−0.2024	0.8147	0.2952	0.051*

	U11	U22	U33	U12	U13	U23
Sn1	0.01341 (6)	0.01614 (6)	0.01448 (6)	0.00001 (4)	0.00225 (4)	0.00191 (4)
C1	0.0176 (7)	0.0170 (7)	0.0159 (7)	−0.0015 (6)	0.0052 (6)	−0.0001 (6)
C2	0.0193 (7)	0.0139 (7)	0.0172 (7)	0.0008 (6)	0.0058 (6)	−0.0002 (6)
C3	0.0149 (7)	0.0168 (7)	0.0175 (7)	0.0016 (6)	0.0014 (6)	−0.0027 (6)
C4	0.0141 (7)	0.0185 (7)	0.0194 (8)	−0.0002 (6)	0.0028 (6)	−0.0020 (6)
C5	0.0170 (8)	0.0210 (8)	0.0232 (8)	0.0027 (6)	0.0013 (6)	0.0000 (6)
C6	0.0559 (14)	0.0607 (15)	0.0314 (11)	0.0330 (12)	0.0074 (10)	−0.0069 (10)
C7	0.0230 (10)	0.0449 (12)	0.0498 (12)	0.0099 (8)	−0.0082 (8)	−0.0115 (10)
C8	0.0319 (12)	0.0326 (11)	0.112 (2)	0.0118 (9)	0.0221 (13)	0.0330 (13)
C9	0.0193 (8)	0.0216 (8)	0.0210 (8)	−0.0044 (6)	0.0036 (6)	0.0011 (6)
C10	0.0302 (10)	0.0268 (9)	0.0270 (9)	−0.0092 (7)	0.0015 (7)	−0.0042 (7)
C11	0.0240 (8)	0.0190 (8)	0.0203 (8)	−0.0009 (6)	0.0027 (6)	0.0041 (6)
C12	0.0343 (10)	0.0299 (9)	0.0195 (8)	−0.0047 (7)	0.0075 (7)	0.0035 (7)
C13	0.0210 (8)	0.0226 (8)	0.0222 (8)	−0.0001 (7)	−0.0030 (6)	0.0014 (7)
C14	0.0234 (9)	0.0293 (9)	0.0472 (12)	0.0069 (7)	−0.0054 (8)	−0.0003 (8)
C15	0.0178 (8)	0.0241 (8)	0.0268 (8)	−0.0037 (6)	0.0033 (6)	0.0017 (7)
C16	0.0355 (10)	0.0252 (9)	0.0433 (11)	−0.0132 (8)	0.0146 (9)	−0.0065 (8)

Sn1—C1	2.1416 (15)	C9—H9A	0.9700
Sn1—C4	2.1475 (16)	C9—H9B	0.9700
Sn1—C5	2.1906 (16)	C10—H10A	0.9600
Sn1—Sn1i	2.7682 (2)	C10—H10B	0.9600
C1—C2	1.347 (2)	C10—H10C	0.9600
C1—C9	1.509 (2)	C11—C12	1.534 (2)
C2—C3	1.507 (2)	C11—H11A	0.9700
C2—C11	1.520 (2)	C11—H11B	0.9700
C3—C4	1.355 (2)	C12—H12A	0.9600
C3—C13	1.518 (2)	C12—H12B	0.9600
C4—C15	1.505 (2)	C12—H12C	0.9600
C5—C8	1.513 (3)	C13—C14	1.529 (2)
C5—C6	1.521 (3)	C13—H13A	0.9700
C5—C7	1.523 (2)	C13—H13B	0.9700
C6—H6A	0.9600	C14—H14A	0.9600
C6—H6B	0.9600	C14—H14B	0.9600
C6—H6C	0.9600	C14—H14C	0.9600
C7—H7A	0.9600	C15—C16	1.516 (2)
C7—H7B	0.9600	C15—H15A	0.9700
C7—H7C	0.9600	C15—H15B	0.9700
C8—H8A	0.9600	C16—H16A	0.9600
C8—H8B	0.9600	C16—H16B	0.9600
C8—H8C	0.9600	C16—H16C	0.9600
C9—C10	1.529 (2)
C1—Sn1—C4	83.75 (6)	C1—C9—H9B	109.1
C1—Sn1—C5	110.28 (6)	C10—C9—H9B	109.1
C4—Sn1—C5	120.31 (6)	H9A—C9—H9B	107.9
C1—Sn1—Sn1i	116.51 (4)	C9—C10—H10A	109.5
C4—Sn1—Sn1i	114.24 (4)	C9—C10—H10B	109.5
C5—Sn1—Sn1i	109.75 (4)	H10A—C10—H10B	109.5
C2—C1—C9	125.63 (14)	C9—C10—H10C	109.5
C2—C1—Sn1	108.27 (11)	H10A—C10—H10C	109.5
C9—C1—Sn1	126.08 (11)	H10B—C10—H10C	109.5
C1—C2—C3	120.03 (13)	C2—C11—C12	112.17 (14)
C1—C2—C11	121.33 (14)	C2—C11—H11A	109.2
C3—C2—C11	118.62 (13)	C12—C11—H11A	109.2
C4—C3—C2	120.22 (14)	C2—C11—H11B	109.2
C4—C3—C13	121.47 (14)	C12—C11—H11B	109.2
C2—C3—C13	118.26 (13)	H11A—C11—H11B	107.9
C3—C4—C15	125.86 (15)	C11—C12—H12A	109.5
C3—C4—Sn1	107.73 (11)	C11—C12—H12B	109.5
C15—C4—Sn1	126.20 (11)	H12A—C12—H12B	109.5
C8—C5—C6	111.14 (18)	C11—C12—H12C	109.5
C8—C5—C7	109.49 (17)	H12A—C12—H12C	109.5
C6—C5—C7	108.65 (17)	H12B—C12—H12C	109.5
C8—C5—Sn1	111.26 (12)	C3—C13—C14	112.16 (14)
C6—C5—Sn1	109.01 (12)	C3—C13—H13A	109.2
C7—C5—Sn1	107.17 (11)	C14—C13—H13A	109.2
C5—C6—H6A	109.5	C3—C13—H13B	109.2
C5—C6—H6B	109.5	C14—C13—H13B	109.2
H6A—C6—H6B	109.5	H13A—C13—H13B	107.9
C5—C6—H6C	109.5	C13—C14—H14A	109.5
H6A—C6—H6C	109.5	C13—C14—H14B	109.5
H6B—C6—H6C	109.5	H14A—C14—H14B	109.5
C5—C7—H7A	109.5	C13—C14—H14C	109.5
C5—C7—H7B	109.5	H14A—C14—H14C	109.5
H7A—C7—H7B	109.5	H14B—C14—H14C	109.5
C5—C7—H7C	109.5	C4—C15—C16	113.80 (14)
H7A—C7—H7C	109.5	C4—C15—H15A	108.8
H7B—C7—H7C	109.5	C16—C15—H15A	108.8
C5—C8—H8A	109.5	C4—C15—H15B	108.8
C5—C8—H8B	109.5	C16—C15—H15B	108.8
H8A—C8—H8B	109.5	H15A—C15—H15B	107.7
C5—C8—H8C	109.5	C15—C16—H16A	109.5
H8A—C8—H8C	109.5	C15—C16—H16B	109.5
H8B—C8—H8C	109.5	H16A—C16—H16B	109.5
C1—C9—C10	112.43 (13)	C15—C16—H16C	109.5
C1—C9—H9A	109.1	H16A—C16—H16C	109.5
C10—C9—H9A	109.1	H16B—C16—H16C	109.5

Sn1—C1	2.1416 (15)
Sn1—C4	2.1475 (16)
Sn1—C5	2.1906 (16)

C1—Sn1—C4

83.75 (6)

Symmetry code: (i) .