(μ-2,3-Dibromo­succinato-κ2O1:O4)bis­[methano­lato-κO)triphenyl­anti­mony(V)]

Quan, L.; Yin, H.; Fu, W.

doi:10.1107/S1600536811016114

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page m713

doi:10.1107/S1600536811016114

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(μ-2,3-Dibromosuccinato-κ²O¹:O⁴)bis[methanolato-κO)triphenylantimony(V)]

Li Quan,^a,^b,^c Handong Yin ^c and Wenfu Fu ^a ^*

^aTechnical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, People's Republic of China, ^bGraduate Unversity of the Chinese Academy of Sciences, Beijing 100049, People's Republic of China, and ^cCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: quanli99@126.com

(Received 25 April 2011; accepted 28 April 2011; online 7 May 2011)

In the title molecule, [Sb₂(C₆H₅)₆(C₄H₄Br₂O₄)(CH₃O)₂], two [Sb(CH₃O)Ph₃]⁺ units are linked by the two carboxylate O atoms of a meso-2,3-dibromosuccinate bridging ligand, forming a dinuclear compound. The Sb^IV atom is five-coordinated in a slightly distorted trigonal–bipyramid geometry by phenyl C atoms in the equatorial positions and two O atoms in the axial positions. C—H⋯O interactions link the molecules into a two-dimensional network parallel to (010). The —CH— group of the centrosymmetric 2,3-dibromosuccinate anion is disordered over two sites in a 0.6:0.4 ratio.

Related literature

For the synthesis and structural characteristics of related organophenylantimony compounds, see: Yin et al. (2008 ).

Experimental

Crystal data

[Sb₂(C₆H₅)₆(C₄H₂Br₂O₄)(CH₃O)₂]
M_r = 1042.04
Triclinic, $[P \overline 1]$
a = 8.707 (8) Å
b = 9.872 (8) Å
c = 12.779 (10) Å
α = 103.74 (2)°
β = 97.93 (2)°
γ = 100.45 (2)°
V = 1030.3 (15) Å³
Z = 1
Mo Kα radiation
μ = 3.29 mm⁻¹
T = 298 K
0.22 × 0.16 × 0.13 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.531, T_max = 0.674
5379 measured reflections
3582 independent reflections
2582 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.131
S = 1.00
3582 reflections
240 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 1.10 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sb1—O3	1.996 (5)
Sb1—C15	2.118 (7)
Sb1—C3	2.119 (7)
Sb1—C9	2.122 (7)
Sb1—O1	2.177 (4)

O3—Sb1—C15	92.7 (2)
O3—Sb1—C3	87.8 (2)
O3—Sb1—C9	93.9 (3)
C15—Sb1—C9	119.3 (3)
C3—Sb1—C9	113.2 (3)
O3—Sb1—O1	176.33 (19)
C15—Sb1—O1	90.7 (2)
C3—Sb1—O1	91.2 (2)
C9—Sb1—O1	83.2 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O2ⁱ	0.93	2.50	3.388 (11)	161
C17—H17⋯O3ⁱⁱ	0.93	2.59	3.435 (10)	152
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x-1, y, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016114/jh2282sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016114/jh2282Isup2.hkl

checkCIF report

Comment top

The similar compound of organotin from meso-2,3-dibromosuccinic acid was synthesized by Professor Yin (Yin et al., 2008). The Sb atom is five-coordinated (Figure 1) with an average Sb-C distance of 2.120 A° almost equal to the average Sn-C distance of 2.123 A° and average Sb-O distance of 2.087 A° much shorter than 2.182 A° of Sn-O distance (Yin et al., 2008). The feature in the solid state structure is the 2D network structure infinitely linked by C19-H19···O2 (2.496 A° of H19···O2) and C17-H17···O3 (2.585 A° of H17···O3) interactions (Figure 2), while the organotin give a 3D network triorganitin(iv) polymer (Yin et al., 2008). The title unit is sited in a symmetrical center, and the coordination environment around the antimony atom is described as a slightly distorted trigonal bipyramid with three carbon atoms from the discrete phenyls in equatorial positions and two oxygen atoms occupying the axial positions with O1-Sb1-O2 angle 176.33 (19)°. The SbC₃ unit is planar (the sum of the C-Sb-C angle is 359.9 °) and the O-Sb-C angles are in the range of 83.2 (2)/93.9 (3)°.

Related literature top

For the synthesis and structural characteristics of related organophenylantimony compounds, see: Yin et al. (2008).

Experimental top

2,3-dibromosuccinic acid (0.276 g, 1.00 mmol) was added to the solution of sodium methoxide (0.108 g, 2.00 mmol) in methanol (15 ml), and the mixture was refluxed with stirring for 30 min. Triphenylantimony chloride (0.423 g, 1.00 mmol) in toluene (25 ml) was then added to the mixture, and the reaction was allowed to continue for 8h under refluxing. After cooling down to room temperature, teh resulting solution was filtered. The solvent was removed by evaporation under vacuum leaving a coloeless solid. The product was recrystallized from dichloromethane/petroleum ether.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of compound (1) showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. 2D network structure infinitely by C19-H19···O2 and C17-H17···O3 interactions [Symmetry code: (i) -x,2-y,1-z; (ii) -1+x,+y,+z].

(µ-2,3-Dibromosuccinato-κ²O¹:O⁴)bis[methanolato- κO)triphenylantimony(V)] top

Crystal data top

[Sb₂(C₆H₅)₆(C₄H₂Br₂O₄)(CH₃O)₂]	Z = 1
M_r = 1042.04	F(000) = 510
Triclinic, P1	D_x = 1.679 Mg m⁻³
a = 8.707 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.872 (8) Å	Cell parameters from 1605 reflections
c = 12.779 (10) Å	θ = 2.4–25.2°
α = 103.74 (2)°	µ = 3.29 mm⁻¹
β = 97.93 (2)°	T = 298 K
γ = 100.45 (2)°	Block, colorless
V = 1030.3 (15) Å³	0.22 × 0.16 × 0.13 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	3582 independent reflections
Radiation source: fine-focus sealed tube	2582 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.531, T_max = 0.674	k = −11→11
5379 measured reflections	l = −8→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0705P)²] where P = (F_o² + 2F_c²)/3
3582 reflections	(Δ/σ)_max < 0.001
240 parameters	Δρ_max = 1.10 e Å⁻³
2 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

[Sb₂(C₆H₅)₆(C₄H₂Br₂O₄)(CH₃O)₂]	γ = 100.45 (2)°
M_r = 1042.04	V = 1030.3 (15) Å³
Triclinic, P1	Z = 1
a = 8.707 (8) Å	Mo Kα radiation
b = 9.872 (8) Å	µ = 3.29 mm⁻¹
c = 12.779 (10) Å	T = 298 K
α = 103.74 (2)°	0.22 × 0.16 × 0.13 mm
β = 97.93 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	3582 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2582 reflections with I > 2σ(I)
T_min = 0.531, T_max = 0.674	R_int = 0.032
5379 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	2 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.00	Δρ_max = 1.10 e Å⁻³
3582 reflections	Δρ_min = −0.68 e Å⁻³
240 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Sb1	0.22561 (5)	0.81465 (5)	0.69951 (4)	0.04269 (19)
Br1	0.22321 (10)	1.18121 (10)	1.08223 (7)	0.0758 (3)
O1	0.1245 (5)	0.8897 (5)	0.8434 (4)	0.0449 (11)
O2	0.0650 (6)	1.0844 (5)	0.8011 (4)	0.0593 (13)
O3	0.3285 (6)	0.7419 (5)	0.5737 (4)	0.0595 (14)
C1	0.0653 (9)	1.0029 (9)	0.8600 (6)	0.0528 (19)
C2	0.028 (2)	1.0561 (18)	0.9733 (9)	0.045 (3)	0.60 (2)
H2	−0.0534	1.1125	0.9678	0.054*	0.60 (2)
C2'	−0.043 (2)	1.001 (3)	0.9429 (16)	0.045 (3)	0.40 (2)
H2'	−0.0900	1.0854	0.9512	0.054*	0.40 (2)
C3	0.4220 (8)	0.9923 (7)	0.7547 (6)	0.0433 (16)
C4	0.4634 (8)	1.0663 (8)	0.8653 (7)	0.059 (2)
H4	0.4005	1.0413	0.9140	0.071*
C5	0.5985 (10)	1.1778 (9)	0.9040 (8)	0.074 (3)
H5	0.6257	1.2256	0.9783	0.089*
C6	0.6886 (10)	1.2161 (10)	0.8353 (9)	0.077 (3)
H6	0.7770	1.2918	0.8612	0.092*
C7	0.6504 (11)	1.1430 (11)	0.7251 (10)	0.086 (3)
H7	0.7145	1.1688	0.6774	0.103*
C8	0.5161 (9)	1.0307 (8)	0.6851 (7)	0.062 (2)
H8	0.4911	0.9822	0.6109	0.074*
C9	0.2537 (8)	0.6454 (7)	0.7711 (6)	0.0472 (17)
C10	0.1370 (10)	0.5804 (8)	0.8189 (7)	0.069 (2)
H10	0.0415	0.6098	0.8200	0.083*
C11	0.1654 (14)	0.4720 (10)	0.8645 (9)	0.096 (3)
H11	0.0868	0.4269	0.8950	0.115*
C12	0.3079 (14)	0.4287 (10)	0.8658 (9)	0.086 (3)
H12	0.3252	0.3558	0.8975	0.103*
C13	0.4230 (12)	0.4940 (10)	0.8202 (8)	0.079 (3)
H13	0.5202	0.4673	0.8225	0.094*
C14	0.3953 (9)	0.6001 (8)	0.7704 (7)	0.061 (2)
H14	0.4721	0.6410	0.7364	0.074*
C15	0.0083 (8)	0.7988 (7)	0.5950 (5)	0.0427 (16)
C16	−0.1375 (9)	0.7702 (8)	0.6290 (7)	0.059 (2)
H16	−0.1398	0.7584	0.6989	0.071*
C17	−0.2776 (10)	0.7594 (10)	0.5594 (9)	0.077 (3)
H17	−0.3734	0.7400	0.5832	0.092*
C18	−0.2792 (12)	0.7763 (10)	0.4578 (9)	0.076 (3)
H18	−0.3747	0.7696	0.4121	0.091*
C19	−0.1357 (13)	0.8041 (9)	0.4223 (7)	0.079 (3)
H19	−0.1355	0.8148	0.3520	0.095*
C20	0.0100 (10)	0.8161 (8)	0.4921 (7)	0.060 (2)
H20	0.1057	0.8356	0.4682	0.072*
C21	0.2653 (11)	0.6019 (9)	0.5003 (7)	0.076 (3)
H21A	0.1873	0.5493	0.5306	0.114*
H21B	0.3498	0.5524	0.4905	0.114*
H21C	0.2167	0.6103	0.4307	0.114*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sb1	0.0395 (3)	0.0443 (3)	0.0438 (3)	0.0105 (2)	0.0141 (2)	0.0065 (2)
Br1	0.0568 (5)	0.0780 (6)	0.0655 (6)	−0.0172 (4)	0.0232 (4)	−0.0143 (5)
O1	0.048 (3)	0.049 (3)	0.043 (3)	0.021 (2)	0.016 (2)	0.013 (2)
O2	0.080 (4)	0.061 (3)	0.048 (3)	0.023 (3)	0.027 (3)	0.022 (3)
O3	0.050 (3)	0.061 (3)	0.062 (3)	0.012 (2)	0.023 (3)	−0.002 (3)
C1	0.055 (4)	0.066 (5)	0.044 (4)	0.020 (4)	0.018 (4)	0.017 (4)
C2	0.057 (10)	0.055 (11)	0.025 (6)	0.025 (7)	0.006 (7)	0.004 (6)
C2'	0.057 (10)	0.055 (11)	0.025 (6)	0.025 (7)	0.006 (7)	0.004 (6)
C3	0.038 (4)	0.044 (4)	0.049 (4)	0.012 (3)	0.011 (3)	0.011 (3)
C4	0.044 (4)	0.067 (5)	0.060 (5)	0.008 (4)	0.013 (4)	0.006 (4)
C5	0.057 (5)	0.070 (6)	0.077 (6)	0.007 (4)	−0.005 (5)	0.000 (5)
C6	0.045 (5)	0.061 (6)	0.109 (8)	0.002 (4)	0.004 (5)	0.008 (6)
C7	0.063 (6)	0.082 (7)	0.121 (9)	0.006 (5)	0.046 (6)	0.034 (7)
C8	0.057 (5)	0.060 (5)	0.070 (6)	0.009 (4)	0.027 (4)	0.018 (4)
C9	0.044 (4)	0.038 (4)	0.051 (4)	0.007 (3)	−0.001 (4)	0.004 (3)
C10	0.065 (5)	0.054 (5)	0.091 (7)	0.010 (4)	0.014 (5)	0.030 (5)
C11	0.105 (8)	0.070 (7)	0.108 (9)	−0.005 (6)	0.014 (7)	0.038 (6)
C12	0.100 (8)	0.052 (6)	0.100 (8)	0.015 (6)	−0.006 (7)	0.023 (5)
C13	0.082 (6)	0.062 (6)	0.088 (7)	0.028 (5)	−0.007 (6)	0.017 (5)
C14	0.061 (5)	0.052 (5)	0.069 (6)	0.017 (4)	0.013 (4)	0.010 (4)
C15	0.048 (4)	0.038 (4)	0.037 (4)	0.006 (3)	0.010 (3)	0.002 (3)
C16	0.054 (5)	0.071 (5)	0.051 (5)	0.019 (4)	0.015 (4)	0.008 (4)
C17	0.044 (5)	0.078 (6)	0.096 (8)	0.015 (4)	0.005 (5)	0.001 (6)
C18	0.069 (6)	0.069 (6)	0.080 (7)	0.018 (5)	−0.018 (5)	0.020 (5)
C19	0.116 (8)	0.067 (6)	0.043 (5)	0.015 (6)	−0.012 (6)	0.014 (4)
C20	0.063 (5)	0.054 (5)	0.057 (5)	0.000 (4)	0.010 (4)	0.014 (4)
C21	0.081 (6)	0.072 (6)	0.068 (6)	0.023 (5)	0.025 (5)	−0.003 (5)

Geometric parameters (Å, º) top

Sb1—O3	1.996 (5)	C8—H8	0.9300
Sb1—C15	2.118 (7)	C9—C14	1.386 (10)
Sb1—C3	2.119 (7)	C9—C10	1.391 (10)
Sb1—C9	2.122 (7)	C10—C11	1.378 (12)
Sb1—O1	2.177 (4)	C10—H10	0.9300
Br1—C2	2.032 (18)	C11—C12	1.383 (14)
Br1—C2'ⁱ	2.09 (2)	C11—H11	0.9300
O1—C1	1.299 (8)	C12—C13	1.366 (14)
O2—C1	1.225 (8)	C12—H12	0.9300
O3—C21	1.435 (9)	C13—C14	1.387 (11)
C1—C2'	1.515 (10)	C13—H13	0.9300
C1—C2	1.521 (9)	C14—H14	0.9300
C2—C2ⁱ	1.48 (3)	C15—C20	1.367 (10)
C2—H2	0.9800	C15—C16	1.401 (10)
C2'—C2'ⁱ	1.56 (5)	C16—C17	1.378 (11)
C2'—Br1ⁱ	2.09 (2)	C16—H16	0.9300
C2'—H2'	0.9800	C17—C18	1.346 (13)
C3—C8	1.362 (10)	C17—H17	0.9300
C3—C4	1.392 (10)	C18—C19	1.390 (13)
C4—C5	1.397 (11)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.414 (12)
C5—C6	1.330 (13)	C19—H19	0.9300
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.383 (14)	C21—H21A	0.9600
C6—H6	0.9300	C21—H21B	0.9600
C7—C8	1.397 (12)	C21—H21C	0.9600
C7—H7	0.9300

O3—Sb1—C15	92.7 (2)	C3—C8—C7	120.0 (8)
O3—Sb1—C3	87.8 (2)	C3—C8—H8	120.0
C15—Sb1—C3	127.3 (3)	C7—C8—H8	120.0
O3—Sb1—C9	93.9 (3)	C14—C9—C10	119.6 (7)
C15—Sb1—C9	119.3 (3)	C14—C9—Sb1	117.8 (6)
C3—Sb1—C9	113.2 (3)	C10—C9—Sb1	122.6 (5)
O3—Sb1—O1	176.33 (19)	C11—C10—C9	118.9 (8)
C15—Sb1—O1	90.7 (2)	C11—C10—H10	120.5
C3—Sb1—O1	91.2 (2)	C9—C10—H10	120.5
C9—Sb1—O1	83.2 (2)	C10—C11—C12	121.6 (10)
C2—Br1—C2'ⁱ	37.5 (5)	C10—C11—H11	119.2
C1—O1—Sb1	123.3 (4)	C12—C11—H11	119.2
C21—O3—Sb1	120.8 (5)	C13—C12—C11	119.3 (9)
O2—C1—O1	125.4 (6)	C13—C12—H12	120.3
O2—C1—C2'	121.6 (11)	C11—C12—H12	120.3
O1—C1—C2'	111.1 (11)	C12—C13—C14	120.2 (9)
O2—C1—C2	116.6 (8)	C12—C13—H13	119.9
O1—C1—C2	116.5 (8)	C14—C13—H13	119.9
C2'—C1—C2	28.0 (7)	C9—C14—C13	120.4 (8)
C2ⁱ—C2—C1	115.5 (14)	C9—C14—H14	119.8
C2ⁱ—C2—Br1	103.3 (13)	C13—C14—H14	119.8
C1—C2—Br1	111.7 (10)	C20—C15—C16	119.3 (7)
C2ⁱ—C2—H2	108.7	C20—C15—Sb1	119.5 (5)
C1—C2—H2	108.7	C16—C15—Sb1	121.2 (5)
Br1—C2—H2	108.7	C17—C16—C15	120.3 (8)
C1—C2'—C2'ⁱ	113.1 (18)	C17—C16—H16	119.9
C1—C2'—Br1ⁱ	118.2 (14)	C15—C16—H16	119.9
C2'ⁱ—C2'—Br1ⁱ	97.0 (18)	C18—C17—C16	121.7 (9)
C1—C2'—H2'	109.3	C18—C17—H17	119.2
C2'ⁱ—C2'—H2'	109.3	C16—C17—H17	119.2
Br1ⁱ—C2'—H2'	109.3	C17—C18—C19	118.9 (8)
C8—C3—C4	118.6 (7)	C17—C18—H18	120.5
C8—C3—Sb1	121.3 (6)	C19—C18—H18	120.5
C4—C3—Sb1	120.0 (5)	C18—C19—C20	120.7 (8)
C3—C4—C5	120.6 (8)	C18—C19—H19	119.7
C3—C4—H4	119.7	C20—C19—H19	119.7
C5—C4—H4	119.7	C15—C20—C19	119.2 (8)
C6—C5—C4	120.5 (9)	C15—C20—H20	120.4
C6—C5—H5	119.8	C19—C20—H20	120.4
C4—C5—H5	119.8	O3—C21—H21A	109.5
C5—C6—C7	119.9 (9)	O3—C21—H21B	109.5
C5—C6—H6	120.1	H21A—C21—H21B	109.5
C7—C6—H6	120.1	O3—C21—H21C	109.5
C6—C7—C8	120.4 (9)	H21A—C21—H21C	109.5
C6—C7—H7	119.8	H21B—C21—H21C	109.5
C8—C7—H7	119.8

Symmetry code: (i) −x, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O2ⁱⁱ	0.93	2.50	3.388 (11)	161
C17—H17···O3ⁱⁱⁱ	0.93	2.59	3.435 (10)	152

Symmetry codes: (ii) −x, −y+2, −z+1; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Sb₂(C₆H₅)₆(C₄H₂Br₂O₄)(CH₃O)₂]
M_r	1042.04
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.707 (8), 9.872 (8), 12.779 (10)
α, β, γ (°)	103.74 (2), 97.93 (2), 100.45 (2)
V (Å³)	1030.3 (15)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	3.29
Crystal size (mm)	0.22 × 0.16 × 0.13

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.531, 0.674
No. of measured, independent and observed [I > 2σ(I)] reflections	5379, 3582, 2582
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.131, 1.00
No. of reflections	3582
No. of parameters	240
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.10, −0.68

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Sb1—O3	1.996 (5)	Sb1—C9	2.122 (7)
Sb1—C15	2.118 (7)	Sb1—O1	2.177 (4)
Sb1—C3	2.119 (7)

O3—Sb1—C15	92.7 (2)	O3—Sb1—O1	176.33 (19)
O3—Sb1—C3	87.8 (2)	C15—Sb1—O1	90.7 (2)
O3—Sb1—C9	93.9 (3)	C3—Sb1—O1	91.2 (2)
C15—Sb1—C9	119.3 (3)	C9—Sb1—O1	83.2 (2)
C3—Sb1—C9	113.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O2ⁱ	0.93	2.50	3.388 (11)	161
C17—H17···O3ⁱⁱ	0.93	2.59	3.435 (10)	152

Symmetry codes: (i) −x, −y+2, −z+1; (ii) x−1, y, z.

Acknowledgements

We acknowledge the National Natural Science Foundation of China for support (grant Nos. 20771053 and 20773059).

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Ctyst. A64, 112–122. CrossRef CAS Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Yin, H. D., Wang, H. Y. & Wang, D. Q. (2008). J. Organomet. Chem. 693, 585–589. CrossRef CAS Google Scholar

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