Triphenyl­bis(2,4,5-trifluoro-3-methoxy­benzoato)anti­mony(V)

Wen, L.; Yin, H.; Quan, L.; Wang, D.

doi:10.1107/S1600536808029656

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1303

doi:10.1107/S1600536808029656

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Triphenylbis(2,4,5-trifluoro-3-methoxybenzoato)antimony(V)

Liyuan Wen,^a Handong Yin,^a ^* Li Quan ^a and Daqi Wang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 11 September 2008; accepted 16 September 2008; online 20 September 2008)

In the title compound, [Sb(C₆H₅)₃(C₈H₄F₃O₃)₂], the Sb atom lies on an inversion centre and exhibits a trigonal bipyramidal geometry with the axial positions occupied by the O atoms of two carboxylate groups and the equatorial positions occupied by C atoms of the phenyl groups. Intramolecular C—H⋯O hydrogen bonds stabilize the molecular conformation. In the crystal structure, molecules are connected by intermolecular C—H⋯O hydrogen-bonding interactions, forming a layer structure parallel to ( $[\overline{2}]$ 01).

Related literature

For related structures, see: Ferguson et al. (1987 ); Ruether et al. (1985 ).

Experimental

Crystal data

[Sb(C₆H₅)₃(C₈H₄F₃O₃)₂]
M_r = 763.27
Monoclinic, C 2/c
a = 12.7970 (14) Å
b = 22.890 (2) Å
c = 12.5131 (10) Å
β = 120.107 (2)°
V = 3170.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.95 mm⁻¹
T = 293 (2) K
0.50 × 0.40 × 0.35 mm

Data collection

Bruker SMART area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.635, T_max = 0.718
7869 measured reflections
2791 independent reflections
2338 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.092
S = 1.01
2791 reflections
215 parameters
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2	0.93	2.36	3.053 (5)	131
C16—H16⋯O1	0.93	2.49	2.979 (5)	113
C8—H8B⋯O3ⁱ	0.96	2.57	3.240 (7)	127
C11—H11⋯O2ⁱⁱ	0.93	2.51	3.255 (5)	138
Symmetry codes: (i) -x, -y+1, -z+2; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808029656/rz2246sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029656/rz2246Isup2.hkl

checkCIF report

Comment top

In recent years organoantimony(V) derivatives have attracted considerable attention due to their significant antimicrobial properties as well as antitumor activities. We have therefore synthesized the title compound, and present its crystal structure here.

The molecular structure of the compound is shown in Fig.1 The Sb atom, which lies on an inversion centre, assumes a distorted trigonal bipyramidal coordination geometry, provided by three phenyl groups at the equatorial positions and two carboxylate groups at the axial positions. The Sb—O bond lengths in organoantimony compounds are extremely variable, ranging from 1.935 Å in triphenylstibine oxide (Ferguson et al. 1987) to 2.506 Å in tetraphenylstibonium benzenesulphonate hydrate (Ruether et al. 1985). The Sb1—O1 distance (2.132 (2) Å) in the title compound lies within this range. The Sb—C bond distances (Sb1—C9 = 2.122 (3) Å; Sb1—C15 = 2.118 (5) Å) fall in the normal range for Sb—C(phenyl) bonds (2.10–2.13 Å). The molecular conformation is stabilized by C—H···O hydrogen bonds. In the crystal packing, molecules are linked by intermolecular C—H···O hydrogen bonds (Fig.2, Table 1,) into layers parallel to the (-2 0 1) plane.

Related literature top

For related structures, see: Ferguson et al. (1987); Ruether et al. (1985).

Experimental top

The reaction was carried out under nitrogen atmosphere. 3-Methoxyl-2,4,5-trifluorobenzoic acid (2 mmol) and sodium ethoxide (2.4 mmol) were added to a stirred solution of methanol (30 ml) in a Schlenk flask and stirred for 0.5 h. Triphenylantimony dichloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at room temperature. The resulting clear solution was evaporated under vacuum. The product was crystallized from a dichloromethane/methanol (1:1 v/v) solution to yield colourless blocks of the title compound (yield 86%. m.p. 458 K). Anal. Calcd (%) for C₃₄H₂₃O₆Sb₁F₆ (Mr = 763.27): C, 53.50; H, 3.04; F, 14.93; Sb, 15.95. Found (%): C, 53.55; H, 3.07; F, 14.89; Sb, 15.99

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity. Symmetry code: (A) = 1 - x, y, 3/2 - z.
	Fig. 2. View of the two-dimensional layer structure in the title compound. Intermolecular hydrogen bonds are shown as dashed lines. H atoms are omitted.

Triphenylbis(2,4,5-trifluoro-3-methoxybenzoato)antimony(V) top

Crystal data top

[Sb(C₆H₅)₃(C₈H₄F₃O₃)₂]	F(000) = 1520
M_r = 763.27	D_x = 1.599 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3589 reflections
a = 12.7970 (14) Å	θ = 2.6–23.9°
b = 22.890 (2) Å	µ = 0.95 mm⁻¹
c = 12.5131 (10) Å	T = 293 K
β = 120.107 (2)°	Block, colourless
V = 3170.9 (5) Å³	0.50 × 0.40 × 0.35 mm
Z = 4

Data collection top

Bruker SMART area-detector diffractometer	2791 independent reflections
Radiation source: fine-focus sealed tube	2338 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→15
T_min = 0.635, T_max = 0.718	k = −27→23
7869 measured reflections	l = −14→14

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.053P)² + 2.3063P] where P = (F_o² + 2F_c²)/3
2791 reflections	(Δ/σ)_max = 0.001
215 parameters	Δρ_max = 0.98 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Sb(C₆H₅)₃(C₈H₄F₃O₃)₂]	V = 3170.9 (5) Å³
M_r = 763.27	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 12.7970 (14) Å	µ = 0.95 mm⁻¹
b = 22.890 (2) Å	T = 293 K
c = 12.5131 (10) Å	0.50 × 0.40 × 0.35 mm
β = 120.107 (2)°

Data collection top

Bruker SMART area-detector diffractometer	2791 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2338 reflections with I > 2σ(I)
T_min = 0.635, T_max = 0.718	R_int = 0.036
7869 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.01	Δρ_max = 0.98 e Å⁻³
2791 reflections	Δρ_min = −0.37 e Å⁻³
215 parameters

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

	x	y	z	U_iso*/U_eq
Sb1	0.5000	0.601220 (13)	0.7500	0.04156 (14)
F1	0.2452 (3)	0.54248 (11)	0.8929 (3)	0.0850 (8)
F2	−0.0110 (3)	0.65440 (19)	0.9796 (3)	0.1229 (13)
F3	0.0513 (3)	0.75229 (15)	0.9055 (3)	0.1104 (11)
O1	0.3684 (2)	0.59621 (10)	0.8065 (2)	0.0501 (6)
O2	0.3552 (2)	0.69304 (12)	0.7893 (3)	0.0614 (7)
O3	0.0880 (4)	0.54671 (19)	0.9730 (4)	0.1077 (13)
C1	0.3247 (3)	0.64637 (17)	0.8139 (3)	0.0501 (9)
C2	0.2343 (3)	0.64523 (17)	0.8571 (3)	0.0515 (9)
C3	0.2004 (4)	0.59594 (19)	0.8951 (4)	0.0608 (11)
C4	0.1193 (4)	0.5976 (2)	0.9386 (5)	0.0745 (14)
C5	0.0708 (4)	0.6507 (3)	0.9410 (5)	0.0808 (15)
C6	0.1022 (4)	0.7004 (3)	0.9027 (5)	0.0789 (14)
C7	0.1836 (3)	0.6985 (2)	0.8621 (4)	0.0612 (10)
H7	0.2052	0.7327	0.8380	0.073*
C8	0.1418 (6)	0.5380 (3)	1.1036 (6)	0.121 (2)
H8A	0.2277	0.5425	1.1423	0.181*
H8B	0.1233	0.4994	1.1192	0.181*
H8C	0.1102	0.5663	1.1367	0.181*
C9	0.6319 (3)	0.63273 (16)	0.9264 (3)	0.0455 (8)
C10	0.6261 (4)	0.68703 (18)	0.9726 (4)	0.0609 (10)
H10	0.5623	0.7123	0.9257	0.073*
C11	0.7170 (4)	0.7030 (2)	1.0897 (4)	0.0752 (13)
H11	0.7134	0.7390	1.1222	0.090*
C12	0.8122 (5)	0.6661 (3)	1.1582 (4)	0.0837 (15)
H12	0.8736	0.6775	1.2360	0.100*
C13	0.8168 (4)	0.6123 (3)	1.1118 (5)	0.0858 (15)
H13	0.8805	0.5870	1.1589	0.103*
C14	0.7263 (4)	0.59551 (19)	0.9947 (4)	0.0675 (12)
H14	0.7298	0.5593	0.9629	0.081*
C15	0.5000	0.5087 (2)	0.7500	0.0441 (11)
C16	0.4754 (4)	0.47799 (17)	0.8308 (4)	0.0601 (10)
H16	0.4585	0.4981	0.8849	0.072*
C17	0.4761 (5)	0.4175 (2)	0.8306 (5)	0.0791 (14)
H17	0.4603	0.3972	0.8853	0.095*
C18	0.5000	0.3873 (3)	0.7500	0.085 (2)
H18	0.5000	0.3466	0.7500	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sb1	0.0500 (2)	0.0384 (2)	0.0411 (2)	0.000	0.02652 (16)	0.000
F1	0.107 (2)	0.0643 (16)	0.114 (2)	−0.0008 (14)	0.0786 (19)	0.0110 (15)
F2	0.092 (2)	0.195 (4)	0.124 (3)	0.005 (2)	0.086 (2)	−0.008 (3)
F3	0.105 (2)	0.126 (3)	0.121 (3)	0.0416 (19)	0.072 (2)	−0.008 (2)
O1	0.0571 (15)	0.0497 (15)	0.0566 (16)	0.0085 (11)	0.0384 (13)	0.0076 (12)
O2	0.0731 (17)	0.0541 (16)	0.0691 (19)	0.0055 (14)	0.0447 (15)	0.0113 (14)
O3	0.117 (3)	0.136 (3)	0.097 (3)	−0.050 (3)	0.074 (2)	−0.004 (3)
C1	0.048 (2)	0.061 (2)	0.042 (2)	0.0083 (17)	0.0229 (17)	0.0064 (17)
C2	0.0451 (19)	0.065 (2)	0.047 (2)	0.0059 (17)	0.0252 (17)	0.0075 (18)
C3	0.058 (2)	0.073 (3)	0.058 (3)	0.001 (2)	0.034 (2)	0.000 (2)
C4	0.064 (3)	0.105 (4)	0.066 (3)	−0.019 (3)	0.041 (2)	−0.001 (3)
C5	0.060 (3)	0.128 (5)	0.070 (3)	0.004 (3)	0.044 (2)	−0.005 (3)
C6	0.064 (3)	0.105 (4)	0.073 (3)	0.019 (3)	0.038 (2)	−0.010 (3)
C7	0.057 (2)	0.071 (3)	0.059 (2)	0.007 (2)	0.031 (2)	0.004 (2)
C8	0.121 (5)	0.135 (5)	0.110 (5)	−0.011 (4)	0.061 (4)	0.011 (5)
C9	0.052 (2)	0.047 (2)	0.041 (2)	−0.0099 (16)	0.0265 (16)	−0.0040 (16)
C10	0.072 (3)	0.055 (2)	0.060 (3)	−0.012 (2)	0.036 (2)	−0.010 (2)
C11	0.088 (3)	0.080 (3)	0.059 (3)	−0.033 (3)	0.039 (3)	−0.023 (2)
C12	0.077 (3)	0.116 (4)	0.051 (3)	−0.039 (3)	0.027 (2)	−0.027 (3)
C13	0.066 (3)	0.113 (4)	0.058 (3)	0.007 (3)	0.016 (2)	0.006 (3)
C14	0.062 (3)	0.077 (3)	0.052 (3)	0.003 (2)	0.020 (2)	−0.008 (2)
C15	0.048 (3)	0.043 (3)	0.040 (3)	0.000	0.022 (2)	0.000
C16	0.082 (3)	0.052 (2)	0.056 (2)	0.000 (2)	0.042 (2)	0.0034 (19)
C17	0.108 (4)	0.054 (3)	0.085 (4)	−0.005 (3)	0.056 (3)	0.013 (2)
C18	0.116 (6)	0.040 (3)	0.102 (6)	0.000	0.056 (5)	0.000

Geometric parameters (Å, º) top

Sb1—C15	2.118 (5)	C8—H8B	0.9600
Sb1—C9	2.122 (3)	C8—H8C	0.9600
Sb1—C9ⁱ	2.122 (3)	C9—C14	1.371 (5)
Sb1—O1ⁱ	2.132 (2)	C9—C10	1.388 (5)
Sb1—O1	2.132 (2)	C10—C11	1.387 (6)
F1—C3	1.358 (5)	C10—H10	0.9300
F2—C5	1.358 (5)	C11—C12	1.372 (7)
F3—C6	1.364 (6)	C11—H11	0.9300
O1—C1	1.301 (4)	C12—C13	1.376 (7)
O2—C1	1.228 (4)	C12—H12	0.9300
O3—C4	1.370 (6)	C13—C14	1.391 (6)
O3—C8	1.434 (7)	C13—H13	0.9300
C1—C2	1.504 (5)	C14—H14	0.9300
C2—C3	1.376 (5)	C15—C16ⁱ	1.390 (4)
C2—C7	1.398 (5)	C15—C16	1.390 (5)
C3—C4	1.393 (6)	C16—C17	1.384 (6)
C4—C5	1.371 (7)	C16—H16	0.9300
C5—C6	1.370 (8)	C17—C18	1.378 (6)
C6—C7	1.369 (6)	C17—H17	0.9300
C7—H7	0.9300	C18—C17ⁱ	1.378 (6)
C8—H8A	0.9600	C18—H18	0.9300

C15—Sb1—C9	109.87 (10)	H8A—C8—H8B	109.5
C15—Sb1—C9ⁱ	109.87 (10)	O3—C8—H8C	109.5
C9—Sb1—C9ⁱ	140.3 (2)	H8A—C8—H8C	109.5
C15—Sb1—O1ⁱ	86.91 (6)	H8B—C8—H8C	109.5
C9—Sb1—O1ⁱ	90.84 (12)	C14—C9—C10	120.7 (4)
C9ⁱ—Sb1—O1ⁱ	91.25 (12)	C14—C9—Sb1	115.4 (3)
C15—Sb1—O1	86.91 (6)	C10—C9—Sb1	123.8 (3)
C9—Sb1—O1	91.25 (12)	C11—C10—C9	118.9 (4)
C9ⁱ—Sb1—O1	90.84 (12)	C11—C10—H10	120.5
O1ⁱ—Sb1—O1	173.83 (12)	C9—C10—H10	120.5
C1—O1—Sb1	114.6 (2)	C12—C11—C10	120.7 (4)
C4—O3—C8	115.3 (5)	C12—C11—H11	119.7
O2—C1—O1	123.2 (3)	C10—C11—H11	119.7
O2—C1—C2	120.3 (3)	C11—C12—C13	119.9 (4)
O1—C1—C2	116.5 (3)	C11—C12—H12	120.0
C3—C2—C7	117.8 (3)	C13—C12—H12	120.0
C3—C2—C1	124.9 (4)	C12—C13—C14	120.2 (5)
C7—C2—C1	117.3 (3)	C12—C13—H13	119.9
F1—C3—C2	121.5 (3)	C14—C13—H13	119.9
F1—C3—C4	116.0 (4)	C9—C14—C13	119.5 (4)
C2—C3—C4	122.5 (4)	C9—C14—H14	120.2
O3—C4—C5	122.7 (5)	C13—C14—H14	120.2
O3—C4—C3	119.5 (5)	C16ⁱ—C15—C16	119.3 (5)
C5—C4—C3	117.8 (4)	C16ⁱ—C15—Sb1	120.3 (2)
F2—C5—C6	119.1 (5)	C16—C15—Sb1	120.3 (2)
F2—C5—C4	120.0 (5)	C17—C16—C15	120.0 (4)
C6—C5—C4	120.9 (4)	C17—C16—H16	120.0
F3—C6—C7	119.9 (5)	C15—C16—H16	120.0
F3—C6—C5	119.1 (4)	C18—C17—C16	120.5 (5)
C7—C6—C5	121.0 (5)	C18—C17—H17	119.7
C6—C7—C2	120.0 (4)	C16—C17—H17	119.7
C6—C7—H7	120.0	C17—C18—C17ⁱ	119.6 (6)
C2—C7—H7	120.0	C17—C18—H18	120.2
O3—C8—H8A	109.5	C17ⁱ—C18—H18	120.2
O3—C8—H8B	109.5

C15—Sb1—O1—C1	−175.3 (2)	C1—C2—C7—C6	−178.9 (4)
C9—Sb1—O1—C1	74.9 (3)	C15—Sb1—C9—C14	25.4 (3)
C9ⁱ—Sb1—O1—C1	−65.5 (3)	C9ⁱ—Sb1—C9—C14	−154.6 (3)
Sb1—O1—C1—O2	0.8 (5)	O1ⁱ—Sb1—C9—C14	−61.7 (3)
Sb1—O1—C1—C2	−178.2 (2)	O1—Sb1—C9—C14	112.5 (3)
O2—C1—C2—C3	−175.3 (4)	C15—Sb1—C9—C10	−154.6 (3)
O1—C1—C2—C3	3.8 (6)	C9ⁱ—Sb1—C9—C10	25.4 (3)
O2—C1—C2—C7	2.9 (5)	O1ⁱ—Sb1—C9—C10	118.3 (3)
O1—C1—C2—C7	−178.1 (3)	O1—Sb1—C9—C10	−67.5 (3)
C7—C2—C3—F1	179.9 (4)	C14—C9—C10—C11	−0.5 (6)
C1—C2—C3—F1	−2.0 (6)	Sb1—C9—C10—C11	179.5 (3)
C7—C2—C3—C4	−0.5 (6)	C9—C10—C11—C12	1.0 (7)
C1—C2—C3—C4	177.6 (4)	C10—C11—C12—C13	−1.4 (7)
C8—O3—C4—C5	−77.2 (7)	C11—C12—C13—C14	1.2 (8)
C8—O3—C4—C3	105.1 (6)	C10—C9—C14—C13	0.4 (7)
F1—C3—C4—O3	−1.5 (7)	Sb1—C9—C14—C13	−179.6 (4)
C2—C3—C4—O3	178.9 (4)	C12—C13—C14—C9	−0.7 (8)
F1—C3—C4—C5	−179.3 (4)	C9—Sb1—C15—C16ⁱ	−119.9 (2)
C2—C3—C4—C5	1.1 (7)	C9ⁱ—Sb1—C15—C16ⁱ	60.1 (2)
O3—C4—C5—F2	0.6 (8)	O1ⁱ—Sb1—C15—C16ⁱ	−30.1 (2)
C3—C4—C5—F2	178.3 (4)	O1—Sb1—C15—C16ⁱ	149.9 (2)
O3—C4—C5—C6	−178.2 (5)	C9—Sb1—C15—C16	60.1 (2)
C3—C4—C5—C6	−0.5 (8)	C9ⁱ—Sb1—C15—C16	−119.9 (2)
F2—C5—C6—F3	0.6 (7)	O1ⁱ—Sb1—C15—C16	149.9 (2)
C4—C5—C6—F3	179.5 (5)	O1—Sb1—C15—C16	−30.1 (2)
F2—C5—C6—C7	−179.5 (4)	C16ⁱ—C15—C16—C17	0.3 (3)
C4—C5—C6—C7	−0.7 (8)	Sb1—C15—C16—C17	−179.7 (3)
F3—C6—C7—C2	−178.9 (4)	C15—C16—C17—C18	−0.6 (7)
C5—C6—C7—C2	1.3 (7)	C16—C17—C18—C17ⁱ	0.3 (3)
C3—C2—C7—C6	−0.7 (6)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2	0.93	2.36	3.053 (5)	131
C16—H16···O1	0.93	2.49	2.979 (5)	113
C8—H8B···O3ⁱⁱ	0.96	2.57	3.240 (7)	127
C11—H11···O2ⁱⁱⁱ	0.93	2.51	3.255 (5)	138

Symmetry codes: (ii) −x, −y+1, −z+2; (iii) x+1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Sb(C₆H₅)₃(C₈H₄F₃O₃)₂]
M_r	763.27
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	12.7970 (14), 22.890 (2), 12.5131 (10)
β (°)	120.107 (2)
V (Å³)	3170.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.50 × 0.40 × 0.35

Data collection
Diffractometer	Bruker SMART area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.635, 0.718
No. of measured, independent and observed [I > 2σ(I)] reflections	7869, 2791, 2338
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.093, 1.01
No. of reflections	2791
No. of parameters	215
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.98, −0.37

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2	0.93	2.36	3.053 (5)	131
C16—H16···O1	0.93	2.49	2.979 (5)	113
C8—H8B···O3ⁱ	0.96	2.57	3.240 (7)	127
C11—H11···O2ⁱⁱ	0.93	2.51	3.255 (5)	138

Symmetry codes: (i) −x, −y+1, −z+2; (ii) x+1/2, −y+3/2, z+1/2.

Acknowledgements

We acknowledge the National Natural Foundation of China (grant No. 20771053) and the Natural Science Foundation of Shandong Province (2005ZX09) for financial support.

References

Ferguson, G., Glidewell, C., Kaitner, B., Lloyd, D. & Metcalfe, S. (1987). Acta Cryst. C43, 824–826. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Ruether, R., Huber, F. & Preut, H. (1985). J. Organomet. Chem. 295, 21–28. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar