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Acta Cryst. (2009). E65, m23    [ doi:10.1107/S1600536808040816 ]

A monoclinic polymorph of (nitrato-[kappa]O)tetraphenylantimony(V)

L. Quan, H. Yin and D. Wang

Abstract top

The asymmetric unit of the title compound, [Sb(C6H5)4(NO3)], contains two crystallographically independent molecules. Each Sb atom exhibits a slightly distorted trigonal-bipyramidal geometry, with the O atom in the apical site. The crystal structure is stabilized by intermolecular C-H...O hydrogen bonds, forming a three-dimensional network.

Comment top

Recently some organoantimony compounds have been reported by our group to possess potential biological activities (Yin et al., 2008). In a continuation of this study, we had synthesized the title compound and report its crystal structure herein. The crystal structure of a first polymorph of the title compound has been previously reported by Sharutin et al. (2002) in the triclinic space group P1, with a = 10.002 (2), b = 12.332 (2), c = 18.758 (5) Å, α = 73.54 (2), β = 75.59 (2), γ = 81.78 (2)°.

As shown in Fig. 1, each antimony atom displays a slightly distorted trigonal bipyramidal geometry, with the equatorial positions occupied by the C atoms of three phenyl groups and the axial positions by one C atom of a phenyl group and one oxygen atom of the nitrate anion. The average Sb—C distance (2.114 Å; Table 1) corresponds well to that found in the triclinic polymorph, and is significantly shorter than the average distance found in [µ2-oxo)-bis((1-phenyl-3-methyl-4-benzoylpyrazolan-5-ato)-triphenyl- antimony(v)] (2.225 Å; Mahon et al., 1998). The average Sb—O distance (2.518 Å) is comparable to that found in the triclinic polymorph (2.521 Å) and remarkably longer than the average distance found in [Me3Sb(O2C–C5H4N)2].H2O (2.145 Å; Chaudhari et al., 2007). In the crystal structure, molecules are linked by C—H···O hydrogen bonds (Table 2) forming chains along the [1 1 0] direction (Fig. 2). The chains are further connected by additional C—H···O hydrogen bonds forming a three-dimensional network (Fig. 3).

Related literature top

For the structure of the triclinic polymorph, see: Sharutin et al. (2002). For the synthesis and structures of related triphenylantimony compounds, see: Yin et al. (2008); Chaudhari et al. (2007); Mahon et al. (1998); Liu et al. (2003).

Experimental top

Silver nitrate (0.339 g, 0.2 mmol) was added to a stirred solution of terraphenylantimonybromide (1.020 g, 0.2 mmol) in toluene (25 ml). After refluxing for 8 h, the resulting black mixture was filtered and the solvent gradually removed by evaporation under vacuum until a white solid was obtained. Colourless crystals suitable for X-ray analysis were obtained by slow evaporation of a petroleum ether/dichloromethane (1:1 v/v) solution.

Refinement top

All H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C).

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. H atoms are omitted for clarity.
[Figure 2] Fig. 2. A partial packing diagram of the title compound showing the formation of chains linked by C—H···O interactions (dotted lines) [Symmetry codes: (i) = 1/2+x, 1/2+y, z; (ii) = 1/2+x, 1/2-y, -1/2+z; (iii) = x, -y, -1/2+z; (iv) = -1/2+x, -1/2+y, z; (v) -1/2+x, -1/2-y -1/2+z; (vi) -1+x, -1+y, z].
[Figure 3] Fig. 3. Packing diagram of the title compound showing the three-dimensional network. Intermolecular C—H···O hydrogen bonds are shown as dotted lines.
(nitrato-κO)tetraphenylantimony(V) top
Crystal data top
[Sb(C6H5)4(NO3)]F(000) = 1968
Mr = 492.17Dx = 1.531 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 4801 reflections
a = 16.7500 (19) Åθ = 2.5–25.5°
b = 12.0274 (12) ŵ = 1.32 mm−1
c = 22.561 (2) ÅT = 298 K
β = 110.054 (2)°Block, colourless
V = 4269.5 (7) Å30.50 × 0.26 × 0.23 mm
Z = 8
Data collection top
Bruker SMART
diffractometer		5811 independent reflections
Radiation source: fine-focus sealed tube5258 reflections with I > 2σ(I)
graphiteRint = 0.028
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→19
Tmin = 0.548, Tmax = 0.737k = −14→13
10559 measured reflectionsl = −26→26
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.056 w = 1/[σ2(Fo2) + (0.018P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
5811 reflectionsΔρmax = 0.53 e Å−3
523 parametersΔρmin = −0.36 e Å−3
3 restraintsAbsolute structure: Flack (1983), 2054 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.033 (18)
Crystal data top
[Sb(C6H5)4(NO3)]V = 4269.5 (7) Å3
Mr = 492.17Z = 8
Monoclinic, CcMo Kα radiation
a = 16.7500 (19) ŵ = 1.32 mm−1
b = 12.0274 (12) ÅT = 298 K
c = 22.561 (2) Å0.50 × 0.26 × 0.23 mm
β = 110.054 (2)°
Data collection top
Bruker SMART
diffractometer		5811 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		5258 reflections with I > 2σ(I)
Tmin = 0.548, Tmax = 0.737Rint = 0.028
10559 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.056Δρmax = 0.53 e Å−3
S = 1.02Δρmin = −0.36 e Å−3
5811 reflectionsAbsolute structure: Flack (1983), 2054 Friedel pairs
523 parametersFlack parameter: −0.033 (18)
3 restraints
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
xyzUiso*/Ueq
Sb10.28494 (2)0.37970 (3)0.346834 (16)0.03919 (10)
Sb20.261037 (18)0.14794 (3)0.063529 (14)0.03867 (10)
N10.0924 (3)0.2489 (4)0.2885 (2)0.0527 (12)
N20.4137 (3)0.0435 (4)0.0215 (2)0.0521 (13)
O10.1687 (3)0.2327 (3)0.2935 (2)0.0587 (12)
O20.0708 (3)0.3394 (4)0.3024 (2)0.0726 (13)
O30.0418 (3)0.1706 (3)0.26967 (19)0.0743 (14)
O40.4020 (3)0.1219 (3)0.05705 (18)0.0508 (10)
O50.3628 (3)−0.0334 (3)0.0056 (2)0.0629 (11)
O60.4767 (3)0.0503 (4)0.0058 (2)0.0801 (15)
C10.3748 (4)0.5073 (4)0.3908 (3)0.0488 (15)
C20.4043 (4)0.5155 (5)0.4552 (3)0.0648 (19)
H20.38760.46330.47900.078*
C30.4584 (5)0.5999 (7)0.4850 (4)0.092 (3)
H30.47870.60470.52880.111*
C40.4818 (5)0.6762 (7)0.4497 (6)0.108 (4)
H40.51580.73570.46980.130*
C50.4570 (6)0.6679 (6)0.3862 (6)0.096 (3)
H50.47700.71800.36320.115*
C60.4013 (4)0.5836 (5)0.3556 (3)0.0682 (19)
H60.38190.57860.31180.082*
C70.2344 (3)0.3543 (4)0.4186 (2)0.0374 (12)
C80.1843 (4)0.4354 (5)0.4318 (3)0.0566 (16)
H80.17070.49970.40740.068*
C90.1546 (4)0.4210 (6)0.4809 (3)0.0676 (19)
H90.11990.47460.48930.081*
C100.1763 (5)0.3269 (6)0.5178 (3)0.065 (2)
H100.15630.31700.55110.078*
C110.2272 (5)0.2479 (5)0.5053 (3)0.0671 (19)
H110.24320.18560.53110.081*
C120.2550 (4)0.2602 (5)0.4549 (3)0.0542 (16)
H120.28760.20480.44550.065*
C130.3632 (4)0.2493 (4)0.3360 (3)0.0427 (14)
C140.4459 (4)0.2747 (5)0.3434 (3)0.0547 (16)
H140.46440.34780.35150.066*
C150.5023 (4)0.1937 (5)0.3390 (3)0.0670 (18)
H150.55760.21250.34260.080*
C160.4757 (5)0.0865 (6)0.3295 (3)0.074 (2)
H160.51290.03130.32610.089*
C170.3960 (5)0.0597 (5)0.3249 (4)0.094 (3)
H170.3783−0.01400.31880.113*
C180.3416 (4)0.1387 (5)0.3291 (4)0.075 (2)
H180.28740.11780.32720.090*
C190.2101 (4)0.4676 (4)0.2660 (3)0.0411 (14)
C200.1778 (4)0.5687 (5)0.2743 (3)0.0570 (17)
H200.19230.59920.31440.068*
C210.1238 (5)0.6253 (5)0.2229 (4)0.063 (2)
H210.10120.69340.22870.075*
C220.1035 (4)0.5821 (6)0.1644 (3)0.0652 (18)
H220.06670.62000.12980.078*
C230.1376 (5)0.4822 (6)0.1561 (3)0.077 (2)
H230.12410.45280.11570.093*
C240.1914 (5)0.4252 (5)0.2067 (3)0.0620 (18)
H240.21490.35800.20060.074*
C250.1390 (4)0.1929 (4)0.0666 (3)0.0388 (13)
C260.1174 (4)0.1793 (4)0.1207 (3)0.0482 (14)
H260.15640.14770.15660.058*
C270.0388 (4)0.2124 (5)0.1214 (3)0.0581 (17)
H270.02460.20200.15740.070*
C28−0.0182 (4)0.2607 (5)0.0686 (3)0.0634 (18)
H28−0.07100.28340.06930.076*
C290.0012 (4)0.2757 (5)0.0155 (3)0.0590 (17)
H29−0.03800.3084−0.02000.071*
C300.0799 (4)0.2420 (4)0.0145 (3)0.0473 (14)
H300.09320.2526−0.02190.057*
C310.2257 (3)0.1317 (4)−0.0351 (2)0.0374 (12)
C320.1621 (4)0.0557 (4)−0.0652 (3)0.0491 (15)
H320.13310.0186−0.04260.059*
C330.1425 (5)0.0358 (5)−0.1281 (3)0.0638 (18)
H330.1006−0.0159−0.14800.077*
C340.1831 (5)0.0900 (6)−0.1621 (3)0.075 (2)
H340.16950.0747−0.20490.090*
C350.2448 (5)0.1682 (6)−0.1332 (3)0.0696 (19)
H350.27130.2072−0.15690.084*
C360.2670 (4)0.1886 (5)−0.0696 (3)0.0538 (16)
H360.30930.2400−0.05000.065*
C370.3313 (4)0.2876 (4)0.1089 (3)0.0415 (14)
C380.3054 (5)0.3906 (5)0.0836 (3)0.081 (2)
H380.25790.39770.04720.097*
C390.3499 (6)0.4832 (6)0.1123 (4)0.096 (3)
H390.33470.55250.09340.115*
C400.4163 (5)0.4753 (5)0.1679 (4)0.076 (2)
H400.44410.53890.18820.092*
C410.4408 (6)0.3744 (6)0.1930 (3)0.085 (3)
H410.48680.36800.23030.102*
C420.3982 (5)0.2797 (5)0.1635 (3)0.076 (2)
H420.41560.21030.18140.092*
C430.2844 (4)0.0027 (4)0.1198 (2)0.0464 (15)
C440.3643 (5)−0.0344 (5)0.1516 (3)0.0638 (19)
H440.41150.00280.14880.077*
C450.3738 (7)−0.1310 (7)0.1892 (4)0.087 (3)
H450.4280−0.15650.21210.104*
C460.3045 (8)−0.1871 (7)0.1923 (4)0.099 (3)
H460.3116−0.25070.21700.118*
C470.2247 (6)−0.1499 (5)0.1589 (4)0.079 (2)
H470.1776−0.18860.16090.095*
C480.2133 (5)−0.0553 (4)0.1223 (3)0.0577 (17)
H480.1589−0.03030.09950.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sb10.0355 (2)0.03932 (17)0.0427 (2)0.00308 (18)0.01348 (18)−0.00078 (17)
Sb20.0315 (2)0.03843 (17)0.0414 (2)0.00229 (18)0.00652 (17)−0.00081 (17)
N10.037 (3)0.065 (3)0.045 (3)−0.008 (3)0.001 (3)0.006 (3)
N20.040 (3)0.054 (3)0.061 (4)0.010 (3)0.016 (3)0.007 (3)
O10.055 (3)0.052 (2)0.063 (3)−0.002 (2)0.011 (3)−0.009 (2)
O20.049 (3)0.061 (3)0.102 (4)0.004 (2)0.019 (3)−0.014 (2)
O30.066 (3)0.070 (3)0.066 (3)−0.032 (3)−0.005 (3)0.006 (2)
O40.038 (2)0.055 (2)0.060 (3)0.000 (2)0.017 (2)−0.012 (2)
O50.051 (3)0.048 (2)0.088 (3)0.002 (2)0.021 (3)−0.012 (2)
O60.066 (3)0.087 (3)0.106 (4)0.004 (3)0.055 (3)−0.003 (3)
C10.037 (4)0.036 (3)0.072 (5)−0.002 (3)0.017 (3)−0.011 (3)
C20.047 (4)0.071 (4)0.067 (5)−0.013 (4)0.008 (4)−0.026 (4)
C30.053 (5)0.099 (6)0.105 (7)−0.011 (5)0.002 (5)−0.047 (5)
C40.059 (6)0.083 (6)0.183 (11)−0.030 (5)0.042 (7)−0.063 (7)
C50.078 (6)0.056 (4)0.181 (10)−0.020 (4)0.077 (7)−0.016 (5)
C60.057 (5)0.058 (4)0.099 (5)−0.011 (3)0.039 (4)−0.004 (4)
C70.028 (3)0.044 (3)0.040 (3)−0.004 (2)0.011 (3)0.002 (2)
C80.058 (4)0.052 (3)0.066 (4)0.008 (3)0.029 (4)0.000 (3)
C90.066 (5)0.070 (4)0.078 (5)−0.006 (4)0.040 (4)−0.022 (4)
C100.068 (5)0.080 (5)0.059 (4)−0.023 (4)0.036 (4)−0.011 (4)
C110.075 (5)0.065 (4)0.068 (5)−0.005 (4)0.032 (4)0.016 (3)
C120.049 (4)0.060 (4)0.061 (4)−0.001 (3)0.028 (4)0.002 (3)
C130.041 (4)0.042 (3)0.048 (4)0.007 (3)0.019 (3)−0.001 (2)
C140.043 (4)0.054 (3)0.070 (5)0.001 (3)0.022 (4)−0.008 (3)
C150.043 (4)0.077 (5)0.088 (5)0.004 (4)0.031 (4)−0.016 (4)
C160.058 (5)0.071 (5)0.094 (5)0.020 (4)0.027 (4)−0.013 (4)
C170.077 (6)0.044 (4)0.172 (8)0.006 (4)0.058 (6)−0.026 (4)
C180.053 (5)0.051 (4)0.124 (7)−0.001 (3)0.034 (5)−0.018 (4)
C190.037 (4)0.038 (3)0.049 (4)−0.001 (3)0.014 (3)0.004 (3)
C200.064 (5)0.056 (4)0.055 (4)0.018 (3)0.025 (4)0.009 (3)
C210.056 (5)0.059 (4)0.078 (5)0.022 (3)0.029 (4)0.019 (4)
C220.050 (4)0.070 (4)0.060 (5)−0.008 (4)−0.001 (4)0.022 (4)
C230.102 (7)0.075 (5)0.039 (4)−0.018 (5)0.003 (4)0.002 (3)
C240.085 (5)0.051 (3)0.045 (4)0.001 (3)0.015 (4)−0.005 (3)
C250.036 (4)0.034 (3)0.040 (3)0.003 (3)0.005 (3)−0.002 (2)
C260.047 (4)0.050 (3)0.043 (3)0.003 (3)0.009 (3)−0.004 (3)
C270.057 (5)0.068 (4)0.057 (4)0.000 (4)0.030 (4)−0.006 (3)
C280.049 (5)0.071 (4)0.073 (5)0.010 (3)0.025 (4)−0.018 (4)
C290.040 (4)0.072 (4)0.055 (4)0.019 (3)0.003 (3)−0.003 (3)
C300.040 (4)0.053 (3)0.046 (4)0.008 (3)0.010 (3)−0.003 (3)
C310.031 (3)0.040 (3)0.038 (3)0.006 (2)0.009 (3)0.002 (2)
C320.038 (4)0.047 (3)0.061 (4)0.001 (3)0.015 (3)−0.005 (3)
C330.059 (5)0.060 (4)0.063 (5)0.002 (3)0.010 (4)−0.020 (3)
C340.079 (6)0.095 (5)0.042 (4)0.028 (5)0.011 (4)−0.011 (4)
C350.075 (5)0.086 (5)0.053 (4)0.016 (4)0.030 (4)0.022 (4)
C360.048 (4)0.055 (3)0.054 (4)−0.003 (3)0.012 (3)0.000 (3)
C370.041 (4)0.036 (3)0.042 (3)0.001 (3)0.007 (3)−0.003 (2)
C380.075 (6)0.048 (4)0.087 (5)−0.007 (4)−0.015 (4)−0.002 (3)
C390.114 (8)0.054 (4)0.094 (6)−0.019 (5)0.000 (6)0.013 (4)
C400.090 (6)0.056 (4)0.073 (5)−0.033 (4)0.015 (5)−0.017 (4)
C410.091 (7)0.065 (5)0.065 (5)−0.019 (4)−0.016 (4)−0.012 (4)
C420.087 (6)0.048 (4)0.069 (5)0.002 (4)−0.006 (4)0.001 (3)
C430.059 (4)0.038 (3)0.040 (4)0.014 (3)0.014 (3)0.000 (3)
C440.062 (5)0.062 (4)0.066 (5)0.021 (4)0.020 (4)0.009 (3)
C450.095 (8)0.088 (6)0.059 (5)0.045 (5)0.002 (5)0.011 (4)
C460.164 (11)0.067 (5)0.073 (6)0.029 (6)0.051 (7)0.017 (4)
C470.119 (8)0.053 (4)0.085 (6)−0.002 (5)0.060 (6)0.009 (4)
C480.069 (5)0.044 (3)0.063 (4)0.000 (3)0.027 (4)0.000 (3)
Geometric parameters (Å, °) top
Sb1—C72.091 (5)C20—C211.381 (9)
Sb1—C192.108 (5)C20—H200.9300
Sb1—C132.111 (5)C21—C221.350 (9)
Sb1—C12.140 (6)C21—H210.9300
Sb1—O12.600 (4)C22—C231.370 (9)
Sb2—C372.105 (5)C22—H220.9300
Sb2—C312.106 (5)C23—C241.371 (9)
Sb2—C432.115 (5)C23—H230.9300
Sb2—C252.139 (6)C24—H240.9300
Sb2—O42.435 (4)C25—C301.382 (7)
Sb2—O42.435 (4)C25—C261.396 (7)
N1—O21.222 (6)C26—C271.381 (8)
N1—O31.240 (6)C26—H260.9300
N1—O31.240 (6)C27—C281.374 (9)
N1—O11.259 (6)C27—H270.9300
N2—O51.224 (6)C28—C291.357 (8)
N2—O61.226 (6)C28—H280.9300
N2—O41.296 (6)C29—C301.387 (8)
N2—O41.296 (6)C29—H290.9300
C1—C21.370 (8)C30—H300.9300
C1—C61.381 (8)C31—C361.386 (7)
C2—C31.373 (9)C31—C321.392 (7)
C2—H20.9300C32—C331.364 (8)
C3—C41.358 (12)C32—H320.9300
C3—H30.9300C33—C341.354 (9)
C4—C51.352 (12)C33—H330.9300
C4—H40.9300C34—C351.384 (10)
C5—C61.391 (10)C34—H340.9300
C5—H50.9300C35—C361.375 (8)
C6—H60.9300C35—H350.9300
C7—C121.370 (7)C36—H360.9300
C7—C81.385 (7)C37—C421.355 (8)
C8—C91.372 (8)C37—C381.371 (7)
C8—H80.9300C38—C391.373 (8)
C9—C101.378 (9)C38—H380.9300
C9—H90.9300C39—C401.365 (10)
C10—C111.369 (9)C39—H390.9300
C10—H100.9300C40—C411.342 (9)
C11—C121.377 (8)C40—H400.9300
C11—H110.9300C41—C421.386 (8)
C12—H120.9300C41—H410.9300
C13—C141.372 (8)C42—H420.9300
C13—C181.373 (7)C43—C441.358 (9)
C14—C151.384 (8)C43—C481.398 (8)
C14—H140.9300C44—C451.415 (10)
C15—C161.357 (9)C44—H440.9300
C15—H150.9300C45—C461.365 (12)
C16—C171.344 (10)C45—H450.9300
C16—H160.9300C46—C471.365 (12)
C17—C181.342 (8)C46—H460.9300
C17—H170.9300C47—C481.381 (8)
C18—H180.9300C47—H470.9300
C19—C241.365 (7)C48—H480.9300
C19—C201.369 (7)
C7—Sb1—C19117.7 (2)C24—C19—C20119.7 (6)
C7—Sb1—C13114.42 (19)C24—C19—Sb1122.0 (4)
C19—Sb1—C13118.7 (2)C20—C19—Sb1118.2 (4)
C7—Sb1—C198.8 (2)C19—C20—C21120.0 (6)
C19—Sb1—C199.0 (2)C19—C20—H20120.0
C13—Sb1—C1102.7 (2)C21—C20—H20120.0
C7—Sb1—O179.68 (17)C22—C21—C20120.3 (6)
C19—Sb1—O179.16 (17)C22—C21—H21119.9
C13—Sb1—O180.63 (19)C20—C21—H21119.9
C1—Sb1—O1176.65 (18)C21—C22—C23119.6 (6)
C37—Sb2—C31119.7 (2)C21—C22—H22120.2
C37—Sb2—C43114.2 (2)C23—C22—H22120.2
C31—Sb2—C43118.98 (18)C22—C23—C24120.7 (6)
C37—Sb2—C2599.4 (2)C22—C23—H23119.6
C31—Sb2—C2597.6 (2)C24—C23—H23119.6
C43—Sb2—C2599.9 (2)C19—C24—C23119.6 (6)
C37—Sb2—O474.92 (18)C19—C24—H24120.2
C31—Sb2—O481.46 (17)C23—C24—H24120.2
C43—Sb2—O486.89 (19)C30—C25—C26117.9 (5)
C25—Sb2—O4172.60 (18)C30—C25—Sb2119.6 (4)
C37—Sb2—O474.92 (18)C26—C25—Sb2122.3 (4)
C31—Sb2—O481.46 (17)C27—C26—C25120.7 (6)
C43—Sb2—O486.89 (19)C27—C26—H26119.7
C25—Sb2—O4172.60 (18)C25—C26—H26119.7
O4—Sb2—O40.0 (2)C28—C27—C26119.6 (6)
O2—N1—O3122.5 (6)C28—C27—H27120.2
O2—N1—O3122.5 (6)C26—C27—H27120.2
O2—N1—O1119.8 (5)C29—C28—C27121.1 (6)
O3—N1—O1117.8 (5)C29—C28—H28119.5
O3—N1—O1117.8 (5)C27—C28—H28119.5
O5—N2—O6123.2 (5)C28—C29—C30119.4 (6)
O5—N2—O4119.5 (5)C28—C29—H29120.3
O6—N2—O4117.3 (5)C30—C29—H29120.3
O5—N2—O4119.5 (5)C29—C30—C25121.3 (6)
O6—N2—O4117.3 (5)C29—C30—H30119.4
N1—O1—Sb1120.8 (3)C25—C30—H30119.4
N2—O4—Sb2119.1 (3)C36—C31—C32119.7 (5)
C2—C1—C6119.5 (6)C36—C31—Sb2122.3 (4)
C2—C1—Sb1118.9 (5)C32—C31—Sb2117.9 (4)
C6—C1—Sb1121.6 (5)C33—C32—C31119.6 (6)
C1—C2—C3120.7 (7)C33—C32—H32120.2
C1—C2—H2119.7C31—C32—H32120.2
C3—C2—H2119.7C34—C33—C32121.1 (6)
C4—C3—C2119.1 (9)C34—C33—H33119.4
C4—C3—H3120.4C32—C33—H33119.4
C2—C3—H3120.4C33—C34—C35119.9 (6)
C5—C4—C3121.7 (8)C33—C34—H34120.1
C5—C4—H4119.1C35—C34—H34120.1
C3—C4—H4119.1C36—C35—C34120.3 (6)
C4—C5—C6119.3 (8)C36—C35—H35119.8
C4—C5—H5120.3C34—C35—H35119.8
C6—C5—H5120.3C35—C36—C31119.3 (6)
C1—C6—C5119.5 (7)C35—C36—H36120.4
C1—C6—H6120.2C31—C36—H36120.4
C5—C6—H6120.2C42—C37—C38119.2 (6)
C12—C7—C8120.0 (5)C42—C37—Sb2122.5 (4)
C12—C7—Sb1119.8 (4)C38—C37—Sb2118.3 (5)
C8—C7—Sb1120.0 (4)C37—C38—C39119.5 (7)
C9—C8—C7119.9 (6)C37—C38—H38120.2
C9—C8—H8120.0C39—C38—H38120.2
C7—C8—H8120.0C40—C39—C38121.1 (6)
C8—C9—C10119.8 (6)C40—C39—H39119.4
C8—C9—H9120.1C38—C39—H39119.4
C10—C9—H9120.1C41—C40—C39119.0 (6)
C11—C10—C9120.0 (6)C41—C40—H40120.5
C11—C10—H10120.0C39—C40—H40120.5
C9—C10—H10120.0C40—C41—C42120.5 (7)
C10—C11—C12120.4 (6)C40—C41—H41119.7
C10—C11—H11119.8C42—C41—H41119.7
C12—C11—H11119.8C37—C42—C41120.5 (6)
C7—C12—C11119.7 (6)C37—C42—H42119.8
C7—C12—H12120.2C41—C42—H42119.8
C11—C12—H12120.2C44—C43—C48120.9 (6)
C14—C13—C18116.4 (5)C44—C43—Sb2122.3 (5)
C14—C13—Sb1117.5 (4)C48—C43—Sb2116.8 (4)
C18—C13—Sb1125.7 (4)C43—C44—C45118.3 (8)
C13—C14—C15121.4 (6)C43—C44—H44120.9
C13—C14—H14119.3C45—C44—H44120.9
C15—C14—H14119.3C46—C45—C44120.9 (8)
C16—C15—C14119.0 (6)C46—C45—H45119.5
C16—C15—H15120.5C44—C45—H45119.5
C14—C15—H15120.5C47—C46—C45119.9 (7)
C17—C16—C15120.2 (6)C47—C46—H46120.1
C17—C16—H16119.9C45—C46—H46120.1
C15—C16—H16119.9C46—C47—C48120.5 (8)
C16—C17—C18120.4 (6)C46—C47—H47119.7
C16—C17—H17119.8C48—C47—H47119.7
C18—C17—H17119.8C47—C48—C43119.4 (7)
C13—C18—C17122.4 (6)C47—C48—H48120.3
C13—C18—H18118.8C43—C48—H48120.3
C17—C18—H18118.8
O2—N1—O1—Sb18.1 (7)Sb1—C19—C20—C21−175.5 (5)
O3—N1—O1—Sb1−171.4 (3)C19—C20—C21—C22−1.0 (10)
O3—N1—O1—Sb1−171.4 (3)C20—C21—C22—C23−0.6 (11)
C7—Sb1—O1—N155.1 (4)C21—C22—C23—C240.6 (11)
C19—Sb1—O1—N1−65.9 (4)C20—C19—C24—C23−2.7 (10)
C13—Sb1—O1—N1172.2 (4)Sb1—C19—C24—C23175.5 (5)
O2—N1—O3—O30.00 (11)C22—C23—C24—C191.0 (11)
O1—N1—O3—O30.00 (14)C37—Sb2—C25—C3097.3 (4)
O5—N2—O4—O40.00 (6)C31—Sb2—C25—C30−24.6 (4)
O6—N2—O4—O40.00 (17)C43—Sb2—C25—C30−145.9 (4)
O5—N2—O4—Sb2−19.6 (6)C37—Sb2—C25—C26−79.6 (4)
O6—N2—O4—Sb2161.1 (4)C31—Sb2—C25—C26158.5 (4)
O4—N2—O4—Sb20(26)C43—Sb2—C25—C2637.2 (5)
C37—Sb2—O4—O40.000 (9)C30—C25—C26—C271.1 (8)
C31—Sb2—O4—O40.00 (4)Sb2—C25—C26—C27178.1 (4)
C43—Sb2—O4—O40.00 (3)C25—C26—C27—C28−1.0 (9)
C37—Sb2—O4—N2−169.9 (4)C26—C27—C28—C290.5 (9)
C31—Sb2—O4—N2−45.8 (4)C27—C28—C29—C30−0.1 (9)
C43—Sb2—O4—N274.1 (4)C28—C29—C30—C250.2 (9)
O4—Sb2—O4—N20(2)C26—C25—C30—C29−0.7 (8)
C7—Sb1—C1—C223.8 (5)Sb2—C25—C30—C29−177.8 (4)
C19—Sb1—C1—C2143.8 (5)C37—Sb2—C31—C3620.3 (5)
C13—Sb1—C1—C2−93.9 (5)C43—Sb2—C31—C36−128.5 (4)
C7—Sb1—C1—C6−153.9 (5)C25—Sb2—C31—C36125.7 (4)
C19—Sb1—C1—C6−33.9 (5)O4—Sb2—C31—C36−46.9 (4)
C13—Sb1—C1—C688.5 (5)O4—Sb2—C31—C36−46.9 (4)
C6—C1—C2—C31.3 (10)C37—Sb2—C31—C32−163.8 (4)
Sb1—C1—C2—C3−176.4 (5)C43—Sb2—C31—C3247.5 (5)
C1—C2—C3—C40.6 (11)C25—Sb2—C31—C32−58.3 (4)
C2—C3—C4—C5−3.6 (13)O4—Sb2—C31—C32129.1 (4)
C3—C4—C5—C64.6 (13)O4—Sb2—C31—C32129.1 (4)
C2—C1—C6—C5−0.4 (9)C36—C31—C32—C331.7 (8)
Sb1—C1—C6—C5177.3 (5)Sb2—C31—C32—C33−174.4 (4)
C4—C5—C6—C1−2.5 (11)C31—C32—C33—C34−1.0 (9)
C19—Sb1—C7—C12148.2 (4)C32—C33—C34—C35−0.9 (10)
C13—Sb1—C7—C121.7 (5)C33—C34—C35—C362.1 (10)
C1—Sb1—C7—C12−106.7 (5)C34—C35—C36—C31−1.4 (10)
O1—Sb1—C7—C1276.4 (4)C32—C31—C36—C35−0.5 (8)
C19—Sb1—C7—C8−35.6 (5)Sb2—C31—C36—C35175.4 (4)
C13—Sb1—C7—C8177.9 (4)C31—Sb2—C37—C42−136.7 (6)
C1—Sb1—C7—C869.5 (5)C43—Sb2—C37—C4213.4 (6)
O1—Sb1—C7—C8−107.4 (5)C25—Sb2—C37—C42118.9 (6)
C12—C7—C8—C9−0.6 (9)O4—Sb2—C37—C42−66.0 (6)
Sb1—C7—C8—C9−176.8 (5)O4—Sb2—C37—C42−66.0 (6)
C7—C8—C9—C101.4 (10)C31—Sb2—C37—C3846.6 (6)
C8—C9—C10—C11−0.1 (10)C43—Sb2—C37—C38−163.2 (5)
C9—C10—C11—C12−2.0 (11)C25—Sb2—C37—C38−57.8 (5)
C8—C7—C12—C11−1.5 (9)O4—Sb2—C37—C38117.3 (5)
Sb1—C7—C12—C11174.7 (5)O4—Sb2—C37—C38117.3 (5)
C10—C11—C12—C72.8 (10)C42—C37—C38—C393.1 (12)
C7—Sb1—C13—C14−120.3 (4)Sb2—C37—C38—C39179.9 (6)
C19—Sb1—C13—C1493.5 (5)C37—C38—C39—C40−4.4 (13)
C1—Sb1—C13—C14−14.3 (5)C38—C39—C40—C413.6 (14)
O1—Sb1—C13—C14165.6 (5)C39—C40—C41—C42−1.5 (14)
C7—Sb1—C13—C1852.0 (6)C38—C37—C42—C41−1.1 (12)
C19—Sb1—C13—C18−94.2 (6)Sb2—C37—C42—C41−177.7 (6)
C1—Sb1—C13—C18158.0 (6)C40—C41—C42—C370.2 (13)
O1—Sb1—C13—C18−22.1 (6)C37—Sb2—C43—C44−49.6 (5)
C18—C13—C14—C155.0 (10)C31—Sb2—C43—C44100.8 (5)
Sb1—C13—C14—C15178.0 (5)C25—Sb2—C43—C44−154.8 (5)
C13—C14—C15—C16−2.4 (10)O4—Sb2—C43—C4422.3 (5)
C14—C15—C16—C17−0.6 (11)O4—Sb2—C43—C4422.3 (5)
C15—C16—C17—C180.7 (13)C37—Sb2—C43—C48131.2 (4)
C14—C13—C18—C17−4.9 (11)C31—Sb2—C43—C48−78.4 (5)
Sb1—C13—C18—C17−177.3 (6)C25—Sb2—C43—C4826.0 (4)
C16—C17—C18—C132.2 (13)O4—Sb2—C43—C48−156.9 (4)
C7—Sb1—C19—C24−126.0 (5)O4—Sb2—C43—C48−156.9 (4)
C13—Sb1—C19—C2419.1 (6)C48—C43—C44—C45−2.2 (9)
C1—Sb1—C19—C24129.0 (5)Sb2—C43—C44—C45178.6 (5)
O1—Sb1—C19—C24−53.8 (5)C43—C44—C45—C461.6 (11)
C7—Sb1—C19—C2052.2 (5)C44—C45—C46—C47−0.2 (12)
C13—Sb1—C19—C20−162.8 (5)C45—C46—C47—C48−0.4 (12)
C1—Sb1—C19—C20−52.8 (5)C46—C47—C48—C43−0.3 (10)
O1—Sb1—C19—C20124.3 (5)C44—C43—C48—C471.6 (9)
C24—C19—C20—C212.7 (9)Sb2—C43—C48—C47−179.1 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C27—H27···O30.932.483.366 (8)160
C45—H45···O2i0.932.553.429 (10)157
C9—H9···O6ii0.932.573.233 (8)129
C40—H40···O3iii0.932.553.449 (8)163
C12—H12···O5iv0.932.553.255 (7)133
C33—H33···O3v0.932.573.414 (8)150
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x−1/2, −y+1/2, z+1/2; (iii) x+1/2, y+1/2, z; (iv) x, −y, z+1/2; (v) x, −y, z−1/2.
Table 1
Selected geometric parameters (Å) top
Sb1—C72.091 (5)Sb2—C312.106 (5)
Sb1—C192.108 (5)Sb2—C432.115 (5)
Sb1—C132.111 (5)Sb2—C252.139 (6)
Sb1—C12.140 (6)Sb2—O42.435 (4)
Sb1—O12.600 (4)Sb2—O42.435 (4)
Sb2—C372.105 (5)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C27—H27···O30.932.483.366 (8)160
C45—H45···O2i0.932.553.429 (10)157
C9—H9···O6ii0.932.573.233 (8)129
C40—H40···O3iii0.932.553.449 (8)163
C12—H12···O5iv0.932.553.255 (7)133
C33—H33···O3v0.932.573.414 (8)150
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x−1/2, −y+1/2, z+1/2; (iii) x+1/2, y+1/2, z; (iv) x, −y, z+1/2; (v) x, −y, z−1/2.
Acknowledgements top

We acknowledge the Nationa Natural Science Foundation of China (grant Nos. 20771053 and #20773059).

references
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