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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): m23.
Published online 2008 December 6. doi:  10.1107/S1600536808040816
PMCID: PMC2967871

A monoclinic polymorph of (nitrato-κO)tetra­phenyl­anti­mony(V)

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-00m23-scheme1.jpg

Experimental

Crystal data

  • [Sb(C6H5)4(NO3)]
  • M r = 492.17
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00m23-efi10.jpg
  • a = 16.7500 (19) Å
  • b = 12.0274 (12) Å
  • c = 22.561 (2) Å
  • β = 110.054 (2)°
  • V = 4269.5 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.32 mm−1
  • T = 298 (2) K
  • 0.50 × 0.26 × 0.23 mm

Data collection

  • Bruker SMART diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.548, T max = 0.737
  • 10559 measured reflections
  • 5811 independent reflections
  • 5258 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.056
  • S = 1.02
  • 5811 reflections
  • 523 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.36 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2054 Friedel pairs
  • Flack parameter: −0.033 (18)

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

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040816/rz2272sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040816/rz2272Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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

Figures

Fig. 1.
The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. H atoms are omitted for clarity.
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) ...
Fig. 3.
Packing diagram of the title compound showing the three-dimensional network. Intermolecular C—H···O hydrogen bonds are shown as dotted lines.

Crystal data

[Sb(C6H5)4(NO3)]F(000) = 1968
Mr = 492.17Dx = 1.531 Mg m3
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 mm1
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

Bruker SMART diffractometer5811 independent reflections
Radiation source: fine-focus sealed tube5258 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] 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

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) = 0.056w = 1/[σ2(Fo2) + (0.018P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
5811 reflectionsΔρmax = 0.53 e Å3
523 parametersΔρmin = −0.36 e Å3
3 restraintsAbsolute structure: Flack (1983), 2054 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.033 (18)

Special details

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)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2272).

References

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