Di-μ-methoxido-μ-oxido-bis­[triphenyl­antimony(V)] methanol disolvate

Betz, R.; Junggeburth, S.; Klüfers, P.; Mayer, P.

doi:10.1107/S1600536809052192

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m28

doi:10.1107/S1600536809052192

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Di-μ-methoxido-μ-oxido-bis[triphenylantimony(V)] methanol disolvate

Richard Betz,^a Sebastian Junggeburth,^a Peter Klüfers ^a ^* and Peter Mayer ^a

^aLudwig-Maximilians Universität, Department Chemie und Biochemie, Butenandtstrasse 5–13 (Haus D), 81377 München, Germany
^*Correspondence e-mail: kluef@cup.uni-muenchen.de

(Received 23 October 2009; accepted 4 December 2009; online 9 December 2009)

The title compound, [Sb₂(C₆H₅)₆(CH₃O)₂O]·2CH₃OH, is the methanol disolvate of a dinuclear triphenylantimony derivative. The molecule shows C_s symmetry. The Sb—O—Sb angles cover a range from 89.65 (10)° to 102.08 (13)°. In the crystal structure, two O—H⋯O hydrogen bonds are present.

Related literature

For related structures, see: Bordner et al. (1986 ). For graph-set analysis, see: Bernstein et al. (1995 ); Etter et al. (1990 ). For the synthesis of triphenylstibane oxide, see: Goodgame & Cotton (1960 ).

Experimental

Crystal data

[Sb₂(C₆H₅)₆(CH₃O)₂O]·2CH₄O
M_r = 848.25
Orthorhombic, P n m a
a = 10.7666 (3) Å
b = 20.9205 (5) Å
c = 16.5619 (5) Å
V = 3730.45 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.49 mm⁻¹
T = 200 K
0.21 × 0.13 × 0.11 mm

Data collection

Oxford Xcalibur KappaCCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, England.]$ ) T_min = 0.923, T_max = 1.000
15055 measured reflections
3877 independent reflections
2632 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.069
S = 1.07
3877 reflections
250 parameters
35 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.16 e Å⁻³
Δρ_min = −0.91 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O90—H90C⋯O1	0.83 (2)	1.90 (3)	2.718 (5)	168 (7)
O91—H91C⋯O90	0.84 (2)	1.81 (2)	2.642 (7)	180 (15)

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-III (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052192/bq2171sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052192/bq2171Isup2.hkl

checkCIF report

Comment top

In a program focused on the synthesis of carbohydrate-derived chelates of members of the p-block of the periodic table of elements, efforts were made to synthesize a diol compound derived from Sb(V). Unintendedly, a dinuclear triphenylantimony derivative was isolated.

In the C_s symmetric molecule, two antimony atoms bearing three phenyl moieties each are connected by two methoxido ligands and one oxido ligand (Fig. 1). The Sb–O–Sb angles cover a range from 90° to 102° with the largest angle on the oxido bridge.

In the crystal structure, two methanol molecules are present which form finite hydrogen bonds (Fig. 2). On the unitary level of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995) the descriptor of this pattern is DD.

Related literature top

For related structures, see Bordner et al. (1986). For graph-set analysis, see Bernstein et al. (1995); Etter et al. (1990). For the synthesis of triphenylstibane oxide, see: Goodgame & Cotton (1960).

Experimental top

The compound was unintendedly prepared upon the attempted condensation of triphenylstibane oxide with a polyol in an aprotic solvent. 1 eq. of triphenylstibane oxide (prepared according to Goodgame & Cotton, 1960) was stirred with 1 eq. of xylitol in dioxane until a clear solution was obtained. After removal of the solvent and subsequent recrystallization from methanol crystals were obtained.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED (Oxford Diffraction, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-III (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms. Symmetry code: i x, -y + 1/2, z.
	Fig. 2. Hydrogen bonds in the crystal structure of the title compound, viewed along [0 1 0]. Symmetry codes: i x + 1/2, y, -z + 1/2; ii x - 1/2, y, -z + 1/2.

Di-µ-methoxido-µ-oxido-bis[triphenylantimony(V)] methanol disolvate top

Crystal data top

[Sb₂(C₆H₅)₆(CH₃O)₂O]·2CH₄O	F(000) = 1704
M_r = 848.25	D_x = 1.510 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 6848 reflections
a = 10.7666 (3) Å	θ = 3.8–26.3°
b = 20.9205 (5) Å	µ = 1.49 mm⁻¹
c = 16.5619 (5) Å	T = 200 K
V = 3730.45 (18) Å³	Rod, colourless
Z = 4	0.21 × 0.13 × 0.11 mm

Data collection top

Oxford Xcalibur KappaCCD diffractometer	3877 independent reflections
Radiation source: fine-focus sealed tube	2632 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω–scans	θ_max = 26.3°, θ_min = 3.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005)	h = −13→10
T_min = 0.923, T_max = 1.000	k = −25→26
15055 measured reflections	l = −20→20

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0343P)²] where P = (F_o² + 2F_c²)/3
3877 reflections	(Δ/σ)_max = 0.001
250 parameters	Δρ_max = 1.16 e Å⁻³
35 restraints	Δρ_min = −0.91 e Å⁻³

Crystal data top

[Sb₂(C₆H₅)₆(CH₃O)₂O]·2CH₄O	V = 3730.45 (18) Å³
M_r = 848.25	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 10.7666 (3) Å	µ = 1.49 mm⁻¹
b = 20.9205 (5) Å	T = 200 K
c = 16.5619 (5) Å	0.21 × 0.13 × 0.11 mm

Data collection top

Oxford Xcalibur KappaCCD diffractometer	3877 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005)	2632 reflections with I > 2σ(I)
T_min = 0.923, T_max = 1.000	R_int = 0.035
15055 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	35 restraints
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 1.16 e Å⁻³
3877 reflections	Δρ_min = −0.91 e Å⁻³
250 parameters

Special details top

Experimental. Absorption correction Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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

	x	y	z	U_iso*/U_eq
C1	0.3088 (3)	0.12147 (15)	0.46497 (18)	0.0318 (7)
C2	0.3241 (3)	0.06249 (15)	0.42762 (19)	0.0351 (8)
H2	0.4048	0.0494	0.4112	0.042*
C3	0.2232 (3)	0.02236 (17)	0.4139 (2)	0.0445 (9)
H3	0.2349	−0.0178	0.3883	0.053*
C4	0.1068 (4)	0.04132 (18)	0.4375 (2)	0.0535 (11)
H4	0.0374	0.0143	0.4281	0.064*
C5	0.0904 (4)	0.0994 (2)	0.4748 (2)	0.0565 (11)
H5	0.0094	0.1121	0.4910	0.068*
C6	0.1907 (3)	0.13995 (18)	0.4893 (2)	0.0448 (9)
H6	0.1784	0.1798	0.5156	0.054*
C7	0.5293 (3)	0.13287 (13)	0.59936 (18)	0.0302 (7)
C8	0.4591 (3)	0.08530 (16)	0.6357 (2)	0.0420 (9)
H8	0.3868	0.0696	0.6096	0.050*
C9	0.4943 (4)	0.06062 (19)	0.7100 (2)	0.0543 (11)
H9	0.4457	0.0281	0.7346	0.065*
C10	0.5977 (5)	0.08263 (18)	0.7479 (2)	0.0640 (13)
H10	0.6195	0.0664	0.7995	0.077*
C11	0.6706 (4)	0.12803 (17)	0.7119 (2)	0.0580 (12)
H11	0.7445	0.1421	0.7377	0.070*
C12	0.6364 (4)	0.15360 (16)	0.6376 (2)	0.0455 (10)
H12	0.6868	0.1854	0.6130	0.055*
C13	0.5940 (3)	0.13122 (14)	0.40116 (18)	0.0289 (7)
C14	0.6844 (3)	0.08906 (17)	0.4273 (2)	0.0450 (9)
H14	0.6913	0.0797	0.4832	0.054*
C15	0.7646 (4)	0.06037 (19)	0.3733 (2)	0.0597 (11)
H15	0.8258	0.0312	0.3919	0.072*
C16	0.7554 (3)	0.07419 (18)	0.2925 (2)	0.0521 (10)
H16	0.8121	0.0555	0.2555	0.063*
C17	0.6651 (4)	0.11463 (16)	0.2649 (2)	0.0464 (9)
H17	0.6579	0.1232	0.2088	0.056*
C18	0.5844 (4)	0.14299 (15)	0.3193 (2)	0.0402 (8)
H18	0.5214	0.1709	0.3000	0.048*
O1	0.5888 (3)	0.2500	0.50194 (15)	0.0258 (7)
O20	0.3612 (3)	0.2500	0.54656 (17)	0.0277 (7)
O21	0.4204 (3)	0.2500	0.40014 (16)	0.0264 (6)
Sb1	0.47467 (2)	0.175954 (8)	0.487384 (12)	0.02407 (8)
C20	0.3345 (5)	0.2500	0.6305 (3)	0.0400 (13)
H20A	0.407 (5)	0.2500	0.660 (3)	0.060*
H20B	0.283 (3)	0.2876 (16)	0.645 (2)	0.060*
C21	0.3109 (5)	0.2500	0.3525 (3)	0.0397 (12)
H21A	0.237 (3)	0.2500	0.385 (3)	0.060*
H21B	0.299 (3)	0.2858 (12)	0.3186 (18)	0.060*
C90	0.8713 (6)	0.2500	0.3896 (4)	0.0681 (18)
O90	0.8368 (3)	0.2500	0.4711 (3)	0.0744 (13)
H90A	0.960 (2)	0.2500	0.385 (5)	0.112*
H90B	0.839 (4)	0.2871 (16)	0.363 (3)	0.112*
H90C	0.7602 (19)	0.2500	0.473 (4)	0.112*
C91	0.9684 (6)	0.2500	0.6588 (5)	0.100 (3)
O91	1.0052 (5)	0.2500	0.5871 (4)	0.176 (4)
H91A	1.038 (3)	0.2500	0.6941 (16)	0.264*
H91B	0.916 (3)	0.2124 (5)	0.665 (2)	0.264*
H91C	0.952 (10)	0.2500	0.550 (6)	0.264*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0364 (19)	0.0323 (17)	0.0268 (18)	−0.0047 (16)	−0.0006 (14)	0.0040 (13)
C2	0.044 (2)	0.0330 (17)	0.0287 (18)	−0.0055 (17)	−0.0045 (16)	0.0053 (14)
C3	0.061 (2)	0.0344 (19)	0.038 (2)	−0.014 (2)	−0.0098 (18)	0.0050 (15)
C4	0.052 (3)	0.060 (3)	0.048 (2)	−0.031 (2)	−0.004 (2)	0.0075 (19)
C5	0.035 (2)	0.075 (3)	0.059 (3)	−0.015 (2)	0.007 (2)	−0.003 (2)
C6	0.039 (2)	0.051 (2)	0.045 (2)	−0.0101 (19)	0.0073 (18)	−0.0066 (17)
C7	0.0411 (19)	0.0259 (16)	0.0236 (16)	0.0067 (16)	0.0000 (16)	−0.0009 (12)
C8	0.047 (2)	0.0409 (19)	0.038 (2)	0.0017 (18)	−0.0001 (18)	0.0110 (16)
C9	0.075 (3)	0.044 (2)	0.043 (2)	0.006 (2)	0.009 (2)	0.0178 (18)
C10	0.114 (4)	0.047 (2)	0.030 (2)	0.023 (3)	−0.009 (2)	0.0055 (19)
C11	0.088 (3)	0.042 (2)	0.043 (2)	0.005 (2)	−0.029 (2)	−0.0004 (18)
C12	0.068 (3)	0.0330 (19)	0.036 (2)	−0.0012 (19)	−0.0146 (19)	0.0029 (15)
C13	0.0324 (18)	0.0252 (16)	0.0291 (17)	−0.0018 (14)	0.0025 (15)	−0.0015 (13)
C14	0.054 (2)	0.053 (2)	0.0282 (19)	0.016 (2)	−0.0059 (18)	−0.0065 (16)
C15	0.058 (3)	0.071 (3)	0.050 (3)	0.033 (2)	−0.009 (2)	−0.016 (2)
C16	0.050 (2)	0.059 (3)	0.047 (2)	0.013 (2)	0.0143 (19)	−0.0154 (19)
C17	0.067 (3)	0.040 (2)	0.032 (2)	−0.001 (2)	0.0106 (19)	−0.0052 (16)
C18	0.053 (2)	0.0347 (19)	0.033 (2)	0.0088 (18)	0.0024 (18)	0.0016 (15)
O1	0.0259 (16)	0.0229 (14)	0.0284 (17)	0.000	−0.0009 (13)	0.000
O20	0.0316 (17)	0.0268 (15)	0.0246 (16)	0.000	0.0054 (14)	0.000
O21	0.0302 (16)	0.0277 (16)	0.0213 (15)	0.000	−0.0026 (13)	0.000
Sb1	0.02763 (12)	0.02247 (11)	0.02209 (12)	−0.00063 (10)	0.00017 (9)	0.00018 (8)
C20	0.051 (3)	0.037 (3)	0.032 (3)	0.000	0.016 (2)	0.000
C21	0.040 (3)	0.042 (3)	0.037 (3)	0.000	−0.014 (2)	0.000
C90	0.058 (4)	0.089 (5)	0.057 (4)	0.000	0.012 (4)	0.000
O90	0.034 (2)	0.140 (4)	0.049 (3)	0.000	−0.001 (2)	0.000
C91	0.062 (5)	0.182 (9)	0.056 (5)	0.000	0.007 (4)	0.000
O91	0.077 (4)	0.385 (12)	0.064 (4)	0.000	0.003 (3)	0.000

Geometric parameters (Å, º) top

C1—C6	1.388 (5)	C15—C16	1.372 (5)
C1—C2	1.390 (4)	C15—H15	0.9500
C1—Sb1	2.151 (3)	C16—C17	1.367 (5)
C2—C3	1.392 (4)	C16—H16	0.9500
C2—H2	0.9500	C17—C18	1.386 (4)
C3—C4	1.372 (5)	C17—H17	0.9500
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.375 (5)	O1—Sb1	1.9921 (18)
C4—H4	0.9500	O1—Sb1ⁱ	1.9922 (18)
C5—C6	1.394 (5)	O20—C20	1.420 (5)
C5—H5	0.9500	O20—Sb1	2.203 (2)
C6—H6	0.9500	O20—Sb1ⁱ	2.203 (2)
C7—C12	1.386 (4)	O21—C21	1.419 (5)
C7—C8	1.387 (4)	O21—Sb1ⁱ	2.1975 (19)
C7—Sb1	2.144 (3)	O21—Sb1	2.1975 (19)
C8—C9	1.388 (5)	Sb1—Sb1ⁱ	3.0981 (4)
C8—H8	0.9500	C20—H20A	0.92 (6)
C9—C10	1.358 (5)	C20—H20B	0.99 (3)
C9—H9	0.9500	C21—H21A	0.956 (19)
C10—C11	1.368 (5)	C21—H21B	0.945 (17)
C10—H10	0.9500	C90—O90	1.400 (8)
C11—C12	1.391 (5)	C90—H90A	0.96 (2)
C11—H11	0.9500	C90—H90B	0.959 (19)
C12—H12	0.9500	O90—H90C	0.83 (2)
C13—C18	1.382 (4)	C91—O91	1.252 (9)
C13—C14	1.383 (4)	C91—H91A	0.95 (2)
C13—Sb1	2.137 (3)	C91—H91B	0.973 (18)
C14—C15	1.381 (5)	O91—H91C	0.84 (2)
C14—H14	0.9500

C6—C1—C2	119.0 (3)	C16—C17—C18	119.6 (3)
C6—C1—Sb1	124.2 (2)	C16—C17—H17	120.2
C2—C1—Sb1	116.6 (2)	C18—C17—H17	120.2
C1—C2—C3	121.0 (3)	C13—C18—C17	121.0 (3)
C1—C2—H2	119.5	C13—C18—H18	119.5
C3—C2—H2	119.5	C17—C18—H18	119.5
C4—C3—C2	119.5 (3)	Sb1—O1—Sb1ⁱ	102.08 (13)
C4—C3—H3	120.3	C20—O20—Sb1	123.25 (17)
C2—C3—H3	120.3	C20—O20—Sb1ⁱ	123.25 (17)
C3—C4—C5	120.1 (4)	Sb1—O20—Sb1ⁱ	89.38 (10)
C3—C4—H4	120.0	C21—O21—Sb1ⁱ	125.92 (15)
C5—C4—H4	120.0	C21—O21—Sb1	125.92 (15)
C4—C5—C6	121.1 (4)	Sb1ⁱ—O21—Sb1	89.65 (10)
C4—C5—H5	119.5	O1—Sb1—C13	92.90 (11)
C6—C5—H5	119.5	O1—Sb1—C7	93.03 (11)
C1—C6—C5	119.3 (3)	C13—Sb1—C7	103.24 (11)
C1—C6—H6	120.3	O1—Sb1—C1	160.95 (11)
C5—C6—H6	120.3	C13—Sb1—C1	98.73 (12)
C12—C7—C8	118.7 (3)	C7—Sb1—C1	98.88 (12)
C12—C7—Sb1	119.5 (2)	O1—Sb1—O21	72.27 (9)
C8—C7—Sb1	121.8 (2)	C13—Sb1—O21	91.67 (10)
C7—C8—C9	120.2 (4)	C7—Sb1—O21	159.72 (9)
C7—C8—H8	119.9	C1—Sb1—O21	92.25 (10)
C9—C8—H8	119.9	O1—Sb1—O20	75.01 (9)
C10—C9—C8	120.4 (4)	C13—Sb1—O20	159.85 (10)
C10—C9—H9	119.8	C7—Sb1—O20	93.61 (10)
C8—C9—H9	119.8	C1—Sb1—O20	89.38 (10)
C9—C10—C11	120.3 (4)	O21—Sb1—O20	69.47 (9)
C9—C10—H10	119.8	O1—Sb1—Sb1ⁱ	38.96 (6)
C11—C10—H10	119.8	C13—Sb1—Sb1ⁱ	115.98 (8)
C10—C11—C12	120.0 (4)	C7—Sb1—Sb1ⁱ	114.86 (8)
C10—C11—H11	120.0	C1—Sb1—Sb1ⁱ	122.00 (9)
C12—C11—H11	120.0	O21—Sb1—Sb1ⁱ	45.18 (5)
C7—C12—C11	120.3 (4)	O20—Sb1—Sb1ⁱ	45.31 (5)
C7—C12—H12	119.9	O20—C20—H20A	110 (3)
C11—C12—H12	119.9	O20—C20—H20B	110 (2)
C18—C13—C14	118.2 (3)	H20A—C20—H20B	111 (3)
C18—C13—Sb1	122.2 (2)	O21—C21—H21A	112 (3)
C14—C13—Sb1	119.6 (2)	O21—C21—H21B	116 (2)
C15—C14—C13	121.0 (3)	H21A—C21—H21B	103 (3)
C15—C14—H14	119.5	O90—C90—H90A	110 (5)
C13—C14—H14	119.5	O90—C90—H90B	111 (3)
C16—C15—C14	119.6 (4)	H90A—C90—H90B	109 (4)
C16—C15—H15	120.2	C90—O90—H90C	108 (5)
C14—C15—H15	120.2	O91—C91—H91A	109 (2)
C17—C16—C15	120.5 (3)	O91—C91—H91B	106 (2)
C17—C16—H16	119.8	H91A—C91—H91B	114 (3)
C15—C16—H16	119.8	C91—O91—H91C	118 (10)

C6—C1—C2—C3	0.6 (5)	C8—C7—Sb1—C13	−102.7 (3)
Sb1—C1—C2—C3	177.0 (2)	C12—C7—Sb1—C1	179.6 (3)
C1—C2—C3—C4	0.0 (5)	C8—C7—Sb1—C1	−1.5 (3)
C2—C3—C4—C5	−0.3 (5)	C12—C7—Sb1—O21	−57.9 (5)
C3—C4—C5—C6	0.0 (6)	C8—C7—Sb1—O21	121.0 (3)
C2—C1—C6—C5	−0.8 (5)	C12—C7—Sb1—O20	−90.5 (3)
Sb1—C1—C6—C5	−177.0 (3)	C8—C7—Sb1—O20	88.4 (3)
C4—C5—C6—C1	0.6 (6)	C12—C7—Sb1—Sb1ⁱ	−48.8 (3)
C12—C7—C8—C9	1.9 (5)	C8—C7—Sb1—Sb1ⁱ	130.0 (2)
Sb1—C7—C8—C9	−177.0 (3)	C6—C1—Sb1—O1	−35.9 (5)
C7—C8—C9—C10	−0.2 (6)	C2—C1—Sb1—O1	147.8 (3)
C8—C9—C10—C11	−2.0 (6)	C6—C1—Sb1—C13	−162.9 (3)
C9—C10—C11—C12	2.4 (6)	C2—C1—Sb1—C13	20.8 (2)
C8—C7—C12—C11	−1.5 (5)	C6—C1—Sb1—C7	92.1 (3)
Sb1—C7—C12—C11	177.4 (3)	C2—C1—Sb1—C7	−84.1 (2)
C10—C11—C12—C7	−0.6 (6)	C6—C1—Sb1—O21	−70.8 (3)
C18—C13—C14—C15	1.3 (5)	C2—C1—Sb1—O21	112.9 (2)
Sb1—C13—C14—C15	−178.7 (3)	C6—C1—Sb1—O20	−1.4 (3)
C13—C14—C15—C16	0.5 (6)	C2—C1—Sb1—O20	−177.7 (2)
C14—C15—C16—C17	−1.9 (6)	C6—C1—Sb1—Sb1ⁱ	−34.7 (3)
C15—C16—C17—C18	1.5 (6)	C2—C1—Sb1—Sb1ⁱ	149.0 (2)
C14—C13—C18—C17	−1.7 (5)	C21—O21—Sb1—O1	−169.6 (3)
Sb1—C13—C18—C17	178.2 (3)	Sb1ⁱ—O21—Sb1—O1	−33.56 (9)
C16—C17—C18—C13	0.3 (5)	C21—O21—Sb1—C13	97.9 (3)
Sb1ⁱ—O1—Sb1—C13	129.41 (12)	Sb1ⁱ—O21—Sb1—C13	−126.07 (11)
Sb1ⁱ—O1—Sb1—C7	−127.15 (12)	C21—O21—Sb1—C7	−124.4 (4)
Sb1ⁱ—O1—Sb1—C1	1.7 (4)	Sb1ⁱ—O21—Sb1—C7	11.6 (4)
Sb1ⁱ—O1—Sb1—O21	38.58 (10)	C21—O21—Sb1—C1	−0.9 (3)
Sb1ⁱ—O1—Sb1—O20	−34.23 (11)	Sb1ⁱ—O21—Sb1—C1	135.13 (11)
C18—C13—Sb1—O1	−90.0 (3)	C21—O21—Sb1—O20	−89.4 (3)
C14—C13—Sb1—O1	89.9 (3)	Sb1ⁱ—O21—Sb1—O20	46.64 (9)
C18—C13—Sb1—C7	176.2 (3)	C21—O21—Sb1—Sb1ⁱ	−136.1 (3)
C14—C13—Sb1—C7	−3.9 (3)	C20—O20—Sb1—O1	−100.6 (3)
C18—C13—Sb1—C1	74.9 (3)	Sb1ⁱ—O20—Sb1—O1	29.84 (9)
C14—C13—Sb1—C1	−105.2 (3)	C20—O20—Sb1—C13	−155.3 (3)
C18—C13—Sb1—O21	−17.6 (3)	Sb1ⁱ—O20—Sb1—C13	−24.9 (4)
C14—C13—Sb1—O21	162.3 (3)	C20—O20—Sb1—C7	−8.4 (3)
C18—C13—Sb1—O20	−37.8 (5)	Sb1ⁱ—O20—Sb1—C7	122.01 (11)
C14—C13—Sb1—O20	142.1 (3)	C20—O20—Sb1—C1	90.4 (3)
C18—C13—Sb1—Sb1ⁱ	−57.3 (3)	Sb1ⁱ—O20—Sb1—C1	−139.13 (11)
C14—C13—Sb1—Sb1ⁱ	122.6 (2)	C20—O20—Sb1—O21	−176.9 (3)
C12—C7—Sb1—O1	−15.3 (3)	Sb1ⁱ—O20—Sb1—O21	−46.50 (9)
C8—C7—Sb1—O1	163.6 (3)	C20—O20—Sb1—Sb1ⁱ	−130.4 (3)
C12—C7—Sb1—C13	78.4 (3)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O90—H90C···O1	0.83 (2)	1.90 (3)	2.718 (5)	168 (7)
O91—H91C···O90	0.84 (2)	1.81 (2)	2.642 (7)	180 (15)

Experimental details

Crystal data
Chemical formula	[Sb₂(C₆H₅)₆(CH₃O)₂O]·2CH₄O
M_r	848.25
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	200
a, b, c (Å)	10.7666 (3), 20.9205 (5), 16.5619 (5)
V (Å³)	3730.45 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.49
Crystal size (mm)	0.21 × 0.13 × 0.11

Data collection
Diffractometer	Oxford Xcalibur KappaCCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2005)
T_min, T_max	0.923, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15055, 3877, 2632
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.069, 1.07
No. of reflections	3877
No. of parameters	250
No. of restraints	35
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.16, −0.91

Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-III (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O90—H90C···O1	0.83 (2)	1.90 (3)	2.718 (5)	168 (7)
O91—H91C···O90	0.84 (2)	1.81 (2)	2.642 (7)	180 (15)

Acknowledgements

The authors thank Prof Klapötke for generous allocation of measurement time on the diffractometer.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bordner, J., Doak, G. O. & Everett, T. S. (1986). J. Am. Chem. Soc. 108, 4206–4213. CSD CrossRef CAS Web of Science Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Goodgame, D. M. L. & Cotton, F. A. (1960). J. Am. Chem. Soc. 82, 5774–5776. CrossRef CAS Web of Science Google Scholar
Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar