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Acta Cryst. (2009). E65, m99    [ doi:10.1107/S1600536808042335 ]

[mu]-Oxido-bis[(2-chloronicotinato-[kappa]O)triphenylantimony(V)]

L. Quan, H. Yin and D. Wang

Abstract top

A new dinuclear triphenylantimony(V) derivative with an oxide bridge, [Sb2(C6H5)6(C6H3ClNO2)2O], has been synthesized. Each Sb atom is five-coordianted by three C atoms and two O atoms in a distorted trigonal-bipyramidal geometry. Metal centers are bridged by a [mu]2-oxide functionality, and phenyl substituents on Sb atoms are in an staggered arrangement. The Sb-O-Sb bridge displays a bent geometry with an angle of 165.1 (4)°. Molecules interact in the crystal through weak C-H...O and C-H...N intermolecular hydrogen bonds.

Comment top

In the title complex, two sets of Sb—O bonds are observed, of which the bridging bond Sb1—O1, 1.955 (5) Å, is the shortest and correspond to the boundary for known range of Sb—O bond lengths in (Ph3SbX)2O species. The shortest coordinating Sb—O bond, Sb1—O2 = 2.208 (5) Å, is associated with the longest C—O bond, C1—O2 = 1.314 (8). In contrast, the long Sb2—O4 bond length, 2.229 (5) Å, is associated to the short C—O bond, C7—O4 = 1.251 (9) Å (Ferguson & Ridley, 1973; Preut et al., 1985, 1986). In the crystal structure, the molecules are connected through weak C—H···O and C—H···N intermolecular hydrogen bonds (Fig. 2.)

Related literature top

For the synthesis and structures of related triphenylantimony compounds, see: Ferguson & Ridley (1973); Preut et al. (1985, 1986).

Experimental top

2-Chloropyridyl-3-carboxylic acid (0.315 g, 2 mmol) was dissolved in dry toluene (15 ml) together with triethylamine (0.202 g, 2 mmol), and the mixture was refluxed for 30 min. Then µ-oxo-bis(triphenylantimony(V)-chloride) (0.423 g, 1 mmol) dissolved in toluene (15 ml) was added. The reaction was allowed to complete for 12 h at room temperature. After filtration, the solvent was gradually removed by evaporation under vacuum, until a white solid was obtained. The solid was recrystallized from petroleum ether/dichloromethane (1:1) to give colourless crystals.

Refinement top

All H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(carrier 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: DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 30% probability level.
[Figure 2] Fig. 2. A 3D network of hydrogen bonds in the crystal structure of the title compound. Symmetry code: (i) x, y+1, z; (ii) -x+1, -y, -z+1; (iii) x, y-1, z; (iv) x, y-1, z.
µ-Oxido-bis[(2-chloronicotinato-κO)triphenylantimony(V)] top
Crystal data top
[Sb2(C6H5)6(C6H3ClNO2)2O]F(000) = 2056
Mr = 1035.19Dx = 1.556 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7208 reflections
a = 20.477 (2) Åθ = 2.3–27.7°
b = 9.6220 (11) ŵ = 1.39 mm−1
c = 22.513 (3) ÅT = 298 K
β = 94.978 (2)°Block, colourless
V = 4419.0 (9) Å30.45 × 0.26 × 0.19 mm
Z = 4
Data collection top
Bruker SMART
diffractometer		7764 independent reflections
Radiation source: fine-focus sealed tube4921 reflections with I > 2σ(I)
graphiteRint = 0.083
φ and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −20→24
Tmin = 0.567, Tmax = 0.770k = −10→11
20773 measured reflectionsl = −17→26
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.045P)2 + 6.3977P]
where P = (Fo2 + 2Fc2)/3
7764 reflections(Δ/σ)max = 0.001
532 parametersΔρmax = 2.07 e Å−3
0 restraintsΔρmin = −1.02 e Å−3
Crystal data top
[Sb2(C6H5)6(C6H3ClNO2)2O]V = 4419.0 (9) Å3
Mr = 1035.19Z = 4
Monoclinic, P21/nMo Kα radiation
a = 20.477 (2) ŵ = 1.39 mm−1
b = 9.6220 (11) ÅT = 298 K
c = 22.513 (3) Å0.45 × 0.26 × 0.19 mm
β = 94.978 (2)°
Data collection top
Bruker SMART
diffractometer		7764 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4921 reflections with I > 2σ(I)
Tmin = 0.567, Tmax = 0.770Rint = 0.083
20773 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.135Δρmax = 2.07 e Å−3
S = 1.05Δρmin = −1.02 e Å−3
7764 reflectionsAbsolute structure: ?
532 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sb10.44005 (2)0.10749 (5)0.19403 (2)0.03649 (16)
Sb20.55296 (2)−0.06381 (5)0.32056 (2)0.03710 (17)
Cl10.40604 (13)0.2694 (4)−0.01255 (13)0.1010 (10)
Cl20.60168 (11)−0.2946 (3)0.51028 (12)0.0704 (7)
N10.2954 (4)0.3827 (9)−0.0438 (4)0.082 (3)
N20.7167 (4)−0.3926 (8)0.5378 (4)0.073 (2)
O10.4918 (2)0.0377 (6)0.2648 (2)0.0554 (15)
O20.3813 (2)0.1832 (5)0.1136 (2)0.0391 (13)
O30.3645 (3)0.3807 (6)0.1607 (3)0.0614 (16)
O40.6211 (2)−0.1640 (5)0.3904 (2)0.0383 (13)
O50.6467 (3)−0.3492 (6)0.3376 (3)0.0603 (16)
C10.3584 (4)0.3045 (9)0.1167 (4)0.042 (2)
C20.3316 (4)0.3395 (10)0.0038 (4)0.064 (3)
C30.3172 (4)0.3516 (9)0.0621 (4)0.047 (2)
C40.2598 (4)0.4261 (9)0.0693 (5)0.065 (3)
H40.24790.44470.10740.079*
C50.2209 (5)0.4719 (11)0.0205 (6)0.088 (4)
H50.18230.52030.02500.105*
C60.2401 (6)0.4449 (12)−0.0338 (6)0.095 (4)
H60.21240.4720−0.06670.114*
C70.6508 (4)−0.2755 (9)0.3831 (3)0.042 (2)
C80.6795 (4)−0.3396 (8)0.4927 (4)0.051 (2)
C90.6964 (4)−0.3276 (9)0.4352 (4)0.050 (2)
C100.7589 (5)−0.3705 (11)0.4241 (5)0.080 (3)
H100.7735−0.36230.38630.095*
C110.7982 (6)−0.4250 (14)0.4703 (6)0.112 (5)
H110.8400−0.45640.46390.135*
C120.7765 (6)−0.4336 (13)0.5256 (6)0.098 (4)
H120.8046−0.46960.55650.117*
C130.3583 (3)0.1332 (8)0.2427 (3)0.0380 (18)
C140.3002 (4)0.0707 (11)0.2244 (4)0.073 (3)
H140.29640.02150.18870.087*
C150.2476 (5)0.0793 (15)0.2578 (6)0.100 (4)
H150.20920.03130.24610.120*
C160.2516 (6)0.1569 (13)0.3072 (6)0.087 (4)
H160.21510.16670.32880.104*
C170.3087 (7)0.2217 (11)0.3261 (5)0.092 (4)
H170.31110.27520.36060.111*
C180.3628 (5)0.2086 (9)0.2947 (4)0.068 (3)
H180.40220.25040.30840.082*
C190.4400 (3)−0.0780 (7)0.1436 (4)0.040 (2)
C200.4469 (4)−0.0785 (10)0.0843 (4)0.064 (3)
H200.45150.00420.06380.077*
C210.4468 (5)−0.2042 (13)0.0552 (6)0.093 (4)
H210.4517−0.20610.01450.112*
C220.4396 (5)−0.3254 (13)0.0847 (8)0.098 (5)
H220.4401−0.40890.06400.118*
C230.4317 (5)−0.3272 (11)0.1441 (7)0.093 (4)
H230.4260−0.41070.16380.112*
C240.4322 (4)−0.2014 (9)0.1747 (5)0.069 (3)
H240.4273−0.19970.21540.082*
C250.5104 (5)0.2593 (12)0.1798 (5)0.086 (4)
C260.5370 (5)0.2649 (12)0.1250 (5)0.096 (4)
H260.52260.20330.09480.116*
C270.5848 (5)0.3614 (12)0.1152 (5)0.098 (4)
H270.60350.36230.07910.117*
C280.6043 (5)0.4540 (12)0.1576 (5)0.093 (4)
H280.63730.51730.15120.112*
C290.5762 (5)0.4552 (11)0.2093 (6)0.094 (4)
H290.58860.52120.23820.113*
C300.5281 (5)0.3567 (10)0.2195 (5)0.078 (3)
H300.50810.35980.25510.094*
C310.6260 (4)−0.0831 (8)0.2614 (3)0.0419 (19)
C320.6865 (5)−0.0301 (13)0.2772 (5)0.099 (4)
H320.69460.01340.31400.119*
C330.7358 (6)−0.0394 (13)0.2399 (6)0.098 (4)
H330.77580.00440.24940.117*
C340.7250 (6)−0.1142 (14)0.1886 (6)0.100 (4)
H340.7594−0.13060.16520.120*
C350.6649 (6)−0.1646 (11)0.1715 (5)0.086 (3)
H350.6573−0.20930.13490.103*
C360.6140 (4)−0.1501 (9)0.2084 (4)0.064 (3)
H360.5726−0.18560.19690.077*
C370.5658 (3)0.1034 (8)0.3808 (4)0.0404 (19)
C380.5912 (5)0.2259 (9)0.3622 (5)0.070 (3)
H380.60130.23670.32300.084*
C390.6016 (6)0.3336 (10)0.4028 (7)0.096 (4)
H390.61920.41700.39080.115*
C400.5864 (5)0.3187 (11)0.4600 (6)0.086 (3)
H400.59390.39190.48670.103*
C410.5608 (5)0.1993 (10)0.4783 (5)0.073 (3)
H410.54940.19010.51720.087*
C420.5515 (4)0.0896 (8)0.4382 (4)0.054 (2)
H420.53530.00540.45100.065*
C430.4813 (4)−0.2111 (8)0.3396 (3)0.0369 (18)
C440.4183 (4)−0.1642 (10)0.3414 (5)0.073 (3)
H440.4081−0.07160.33310.088*
C450.3699 (5)−0.2554 (13)0.3558 (5)0.088 (4)
H450.3271−0.22360.35670.105*
C460.3837 (5)−0.3904 (12)0.3687 (5)0.080 (3)
H460.3506−0.45100.37780.096*
C470.4452 (5)−0.4351 (10)0.3680 (5)0.082 (3)
H470.4551−0.52720.37770.099*
C480.4944 (4)−0.3475 (9)0.3532 (4)0.067 (3)
H480.5369−0.38120.35250.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sb10.0423 (3)0.0373 (3)0.0291 (3)−0.0034 (2)−0.0012 (2)0.0032 (2)
Sb20.0417 (3)0.0410 (3)0.0281 (3)−0.0049 (2)0.0002 (2)0.0047 (2)
Cl10.0790 (18)0.172 (3)0.0542 (18)0.0339 (19)0.0204 (15)0.0190 (19)
Cl20.0636 (14)0.0895 (18)0.0606 (17)0.0100 (13)0.0190 (13)0.0172 (14)
N10.082 (6)0.105 (7)0.056 (6)0.017 (5)−0.008 (5)0.021 (5)
N20.080 (6)0.087 (6)0.049 (5)0.011 (5)−0.007 (5)0.014 (5)
O10.052 (3)0.066 (4)0.046 (4)−0.011 (3)−0.012 (3)0.022 (3)
O20.051 (3)0.033 (3)0.032 (3)0.003 (2)−0.005 (3)0.003 (2)
O30.087 (4)0.045 (4)0.052 (4)0.000 (3)0.005 (3)0.001 (3)
O40.052 (3)0.029 (3)0.033 (3)0.004 (2)−0.003 (3)0.005 (2)
O50.079 (4)0.057 (4)0.044 (4)0.005 (3)0.000 (3)−0.002 (3)
C10.047 (5)0.054 (6)0.025 (5)−0.009 (4)0.003 (4)0.006 (4)
C20.053 (5)0.081 (7)0.055 (7)0.009 (5)−0.002 (5)0.019 (5)
C30.040 (5)0.076 (6)0.027 (5)−0.012 (4)0.007 (4)0.000 (4)
C40.057 (6)0.061 (6)0.077 (7)0.015 (5)0.001 (5)0.006 (5)
C50.074 (7)0.075 (8)0.110 (11)0.032 (6)−0.012 (7)0.010 (8)
C60.097 (9)0.108 (10)0.073 (9)0.022 (7)−0.036 (8)0.021 (8)
C70.052 (5)0.053 (6)0.020 (5)−0.006 (4)−0.002 (4)0.003 (4)
C80.056 (5)0.053 (5)0.044 (6)0.005 (4)−0.001 (5)0.002 (4)
C90.050 (5)0.053 (5)0.045 (6)0.005 (4)−0.002 (4)0.000 (4)
C100.068 (6)0.120 (9)0.052 (7)0.031 (6)0.011 (5)0.003 (6)
C110.085 (8)0.163 (13)0.085 (10)0.069 (8)−0.011 (8)−0.006 (9)
C120.082 (8)0.136 (11)0.070 (9)0.049 (7)−0.017 (7)0.010 (8)
C130.045 (4)0.041 (5)0.028 (5)0.000 (4)0.007 (4)0.003 (4)
C140.053 (5)0.121 (9)0.045 (6)−0.019 (6)0.004 (5)−0.008 (6)
C150.058 (7)0.168 (13)0.076 (9)−0.023 (7)0.013 (6)0.021 (9)
C160.072 (8)0.116 (10)0.077 (9)0.027 (7)0.034 (7)0.028 (8)
C170.136 (11)0.072 (8)0.076 (9)0.008 (7)0.051 (9)−0.012 (7)
C180.088 (7)0.064 (6)0.058 (7)−0.023 (5)0.032 (6)−0.020 (5)
C190.041 (4)0.028 (5)0.051 (6)0.000 (3)−0.005 (4)−0.002 (4)
C200.069 (6)0.072 (7)0.054 (7)0.003 (5)0.014 (5)−0.017 (6)
C210.094 (8)0.090 (9)0.098 (10)0.010 (7)0.028 (7)−0.050 (8)
C220.081 (8)0.059 (8)0.156 (15)−0.002 (6)0.015 (9)−0.050 (10)
C230.103 (9)0.046 (7)0.131 (13)−0.014 (6)0.019 (9)−0.015 (8)
C240.068 (6)0.055 (6)0.083 (8)−0.014 (5)0.007 (6)−0.012 (6)
C250.088 (7)0.116 (9)0.056 (7)−0.058 (7)0.015 (6)−0.007 (7)
C260.098 (8)0.126 (10)0.067 (8)−0.060 (7)0.020 (7)−0.010 (7)
C270.100 (8)0.129 (10)0.067 (8)−0.058 (8)0.021 (7)−0.007 (8)
C280.094 (8)0.122 (10)0.065 (8)−0.060 (7)0.018 (7)−0.006 (8)
C290.118 (9)0.069 (7)0.095 (10)−0.049 (7)0.014 (8)−0.016 (7)
C300.087 (7)0.080 (7)0.072 (8)−0.031 (6)0.028 (6)−0.017 (6)
C310.045 (4)0.051 (5)0.031 (5)−0.011 (4)0.009 (4)0.007 (4)
C320.056 (6)0.190 (13)0.054 (7)−0.041 (7)0.022 (6)−0.008 (8)
C330.096 (9)0.131 (11)0.068 (8)−0.055 (8)0.019 (7)−0.006 (8)
C340.068 (8)0.151 (12)0.088 (10)0.004 (8)0.040 (7)0.005 (9)
C350.115 (9)0.096 (8)0.052 (7)0.003 (7)0.038 (7)−0.010 (6)
C360.069 (6)0.073 (7)0.053 (7)−0.016 (5)0.018 (5)−0.012 (5)
C370.047 (4)0.036 (5)0.038 (5)−0.001 (4)0.004 (4)−0.001 (4)
C380.099 (8)0.036 (5)0.078 (8)−0.008 (5)0.015 (6)0.005 (5)
C390.135 (10)0.028 (6)0.128 (12)−0.018 (6)0.028 (9)0.006 (7)
C400.103 (9)0.054 (7)0.101 (11)−0.003 (6)0.018 (8)−0.025 (7)
C410.090 (7)0.069 (7)0.062 (7)−0.011 (6)0.022 (6)−0.027 (6)
C420.069 (6)0.040 (5)0.056 (6)−0.012 (4)0.014 (5)−0.007 (5)
C430.051 (5)0.047 (5)0.013 (4)−0.008 (4)0.003 (3)0.001 (4)
C440.059 (6)0.066 (6)0.097 (9)−0.007 (5)0.023 (6)0.011 (6)
C450.056 (6)0.107 (10)0.105 (10)−0.024 (6)0.035 (6)−0.002 (8)
C460.080 (8)0.083 (8)0.079 (8)−0.048 (7)0.019 (6)0.006 (7)
C470.094 (8)0.055 (6)0.098 (9)−0.032 (6)0.007 (7)0.022 (6)
C480.060 (6)0.062 (6)0.076 (8)−0.012 (5)0.001 (5)0.009 (6)
Geometric parameters (Å, °) top
Sb1—O11.955 (5)C21—C221.356 (16)
Sb1—C132.094 (7)C21—H210.9300
Sb1—C252.095 (9)C22—C231.360 (17)
Sb1—C192.115 (7)C22—H220.9300
Sb1—O22.208 (5)C23—C241.392 (14)
Sb2—O11.955 (5)C23—H230.9300
Sb2—C312.096 (8)C24—H240.9300
Sb2—C372.106 (8)C25—C301.325 (13)
Sb2—C432.111 (7)C25—C261.393 (14)
Sb2—O42.229 (5)C26—C271.380 (12)
Cl1—C21.735 (9)C26—H260.9300
Cl2—C81.730 (9)C27—C281.340 (14)
N1—C61.317 (14)C27—H270.9300
N1—C21.317 (11)C28—C291.343 (14)
N2—C81.319 (10)C28—H280.9300
N2—C121.336 (13)C29—C301.400 (12)
O2—C11.261 (9)C29—H290.9300
O3—C11.232 (9)C30—H300.9300
O4—C71.251 (9)C31—C321.358 (11)
O5—C71.244 (9)C31—C361.360 (11)
C1—C31.498 (10)C32—C331.372 (14)
C2—C31.376 (12)C32—H320.9300
C3—C41.398 (11)C33—C341.362 (16)
C4—C51.372 (14)C33—H330.9300
C4—H40.9300C34—C351.347 (14)
C5—C61.343 (15)C34—H340.9300
C5—H50.9300C35—C361.395 (13)
C6—H60.9300C35—H350.9300
C7—C91.518 (10)C36—H360.9300
C8—C91.374 (12)C37—C421.356 (11)
C9—C101.388 (11)C37—C381.369 (11)
C10—C111.364 (14)C38—C391.386 (14)
C10—H100.9300C38—H380.9300
C11—C121.361 (16)C39—C401.357 (15)
C11—H110.9300C39—H390.9300
C12—H120.9300C40—C411.344 (13)
C13—C141.363 (10)C40—H400.9300
C13—C181.373 (11)C41—C421.391 (11)
C14—C151.369 (14)C41—H410.9300
C14—H140.9300C42—H420.9300
C15—C161.338 (16)C43—C481.369 (11)
C15—H150.9300C43—C441.371 (11)
C16—C171.361 (15)C44—C451.382 (12)
C16—H160.9300C44—H440.9300
C17—C181.372 (13)C45—C461.355 (13)
C17—H170.9300C45—H450.9300
C18—H180.9300C46—C471.332 (13)
C19—C201.354 (12)C46—H460.9300
C19—C241.395 (11)C47—C481.377 (12)
C20—C211.376 (13)C47—H470.9300
C20—H200.9300C48—H480.9300
O1—Sb1—C1390.9 (3)C22—C21—C20121.2 (12)
O1—Sb1—C2591.9 (3)C22—C21—H21119.4
C13—Sb1—C25126.1 (4)C20—C21—H21119.4
O1—Sb1—C1997.0 (3)C21—C22—C23121.3 (11)
C13—Sb1—C19114.7 (3)C21—C22—H22119.4
C25—Sb1—C19118.3 (4)C23—C22—H22119.4
O1—Sb1—O2179.2 (2)C22—C23—C24118.7 (12)
C13—Sb1—O289.2 (2)C22—C23—H23120.7
C25—Sb1—O288.7 (3)C24—C23—H23120.7
C19—Sb1—O282.2 (2)C23—C24—C19119.1 (11)
O1—Sb2—C3195.1 (3)C23—C24—H24120.4
O1—Sb2—C3793.9 (3)C19—C24—H24120.4
C31—Sb2—C37114.9 (3)C30—C25—C26117.8 (9)
O1—Sb2—C4392.7 (2)C30—C25—Sb1122.8 (8)
C31—Sb2—C43128.1 (3)C26—C25—Sb1119.3 (8)
C37—Sb2—C43115.6 (3)C27—C26—C25120.3 (11)
O1—Sb2—O4174.6 (2)C27—C26—H26119.9
C31—Sb2—O488.4 (2)C25—C26—H26119.9
C37—Sb2—O480.8 (2)C28—C27—C26120.4 (11)
C43—Sb2—O488.3 (2)C28—C27—H27119.8
C6—N1—C2115.8 (10)C26—C27—H27119.8
C8—N2—C12115.8 (9)C27—C28—C29119.9 (10)
Sb1—O1—Sb2165.1 (4)C27—C28—H28120.0
C1—O2—Sb1116.1 (5)C29—C28—H28120.0
C7—O4—Sb2124.1 (5)C28—C29—C30119.8 (11)
O3—C1—O2125.6 (7)C28—C29—H29120.1
O3—C1—C3119.3 (8)C30—C29—H29120.1
O2—C1—C3114.9 (8)C25—C30—C29121.5 (11)
N1—C2—C3126.8 (9)C25—C30—H30119.3
N1—C2—Cl1113.1 (8)C29—C30—H30119.3
C3—C2—Cl1120.0 (7)C32—C31—C36120.0 (8)
C2—C3—C4113.9 (8)C32—C31—Sb2119.0 (7)
C2—C3—C1127.2 (8)C36—C31—Sb2121.0 (6)
C4—C3—C1118.7 (8)C31—C32—C33121.2 (10)
C5—C4—C3120.5 (10)C31—C32—H32119.4
C5—C4—H4119.7C33—C32—H32119.4
C3—C4—H4119.7C34—C33—C32118.6 (10)
C6—C5—C4118.1 (10)C34—C33—H33120.7
C6—C5—H5120.9C32—C33—H33120.7
C4—C5—H5120.9C35—C34—C33120.7 (11)
N1—C6—C5124.6 (10)C35—C34—H34119.6
N1—C6—H6117.7C33—C34—H34119.6
C5—C6—H6117.7C34—C35—C36120.3 (11)
O5—C7—O4126.7 (7)C34—C35—H35119.9
O5—C7—C9116.2 (8)C36—C35—H35119.9
O4—C7—C9117.1 (7)C31—C36—C35118.9 (9)
N2—C8—C9125.5 (8)C31—C36—H36120.6
N2—C8—Cl2113.8 (7)C35—C36—H36120.6
C9—C8—Cl2120.5 (6)C42—C37—C38119.6 (8)
C8—C9—C10117.2 (8)C42—C37—Sb2120.9 (6)
C8—C9—C7124.5 (8)C38—C37—Sb2119.4 (7)
C10—C9—C7118.3 (9)C37—C38—C39118.9 (10)
C11—C10—C9118.0 (10)C37—C38—H38120.5
C11—C10—H10121.0C39—C38—H38120.5
C9—C10—H10121.0C40—C39—C38120.8 (10)
C12—C11—C10120.2 (10)C40—C39—H39119.6
C12—C11—H11119.9C38—C39—H39119.6
C10—C11—H11119.9C41—C40—C39120.6 (10)
N2—C12—C11123.2 (10)C41—C40—H40119.7
N2—C12—H12118.4C39—C40—H40119.7
C11—C12—H12118.4C40—C41—C42119.0 (10)
C14—C13—C18118.9 (8)C40—C41—H41120.5
C14—C13—Sb1120.4 (6)C42—C41—H41120.5
C18—C13—Sb1120.7 (6)C37—C42—C41121.1 (8)
C13—C14—C15121.0 (10)C37—C42—H42119.5
C13—C14—H14119.5C41—C42—H42119.5
C15—C14—H14119.5C48—C43—C44118.4 (8)
C16—C15—C14119.8 (11)C48—C43—Sb2124.3 (6)
C16—C15—H15120.1C44—C43—Sb2117.3 (6)
C14—C15—H15120.1C43—C44—C45119.5 (9)
C15—C16—C17120.3 (11)C43—C44—H44120.2
C15—C16—H16119.9C45—C44—H44120.2
C17—C16—H16119.9C46—C45—C44121.3 (10)
C16—C17—C18120.5 (11)C46—C45—H45119.4
C16—C17—H17119.7C44—C45—H45119.4
C18—C17—H17119.7C47—C46—C45119.1 (9)
C17—C18—C13119.4 (10)C47—C46—H46120.4
C17—C18—H18120.3C45—C46—H46120.4
C13—C18—H18120.3C46—C47—C48121.1 (10)
C20—C19—C24121.2 (8)C46—C47—H47119.4
C20—C19—Sb1122.5 (6)C48—C47—H47119.4
C24—C19—Sb1116.3 (7)C43—C48—C47120.6 (9)
C19—C20—C21118.5 (10)C43—C48—H48119.7
C19—C20—H20120.8C47—C48—H48119.7
C21—C20—H20120.8
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C17—H17···N2i0.932.663.556 (14)163
C39—H39···O5ii0.932.633.544 (12)167
C23—H23···O3iii0.932.373.166 (12)144
C23—H23···O3iii0.932.373.166 (12)144
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y+1, z; (iii) x, y−1, z.
Table 1
Selected geometric parameters (Å, °) top
Sb1—O11.955 (5)Sb2—O11.955 (5)
Sb1—O22.208 (5)Sb2—O42.229 (5)
O1—Sb1—O2179.2 (2)Sb1—O1—Sb2165.1 (4)
O1—Sb2—O4174.6 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C17—H17···N2i0.932.663.556 (14)163
C39—H39···O5ii0.932.633.544 (12)167
C23—H23···O3iii0.932.373.166 (12)144
C23—H23···O3iii0.932.373.166 (12)144
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y+1, z; (iii) x, y−1, z.
Acknowledgements top

We acknowledge the National Natural Science Foundation of China (grant No. 20771053).

references
References top

Brandenburg, K. (1998). DIAMOND. University of Bonn, Germany.

Ferguson, G. & Ridley, D. R. (1973). Acta Cryst. B29, 2221–2226.

Preut, H., Rüther, R. & Huber, F. (1985). Acta Cryst. C41, 358–360.

Preut, H., Rüther, R. & Huber, F. (1986). Acta Cryst. C42, 1154–1157.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Ctyst. A63, 112-122.

Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.