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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): m99.
Published online 2008 December 20. doi:  10.1107/S1600536808042335
PMCID: PMC2967930

μ-Oxido-bis­[(2-chloro­nicotinato-κO)triphenyl­anti­mony(V)]

Abstract

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 μ2-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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-00m99-scheme1.jpg

Experimental

Crystal data

  • [Sb2(C6H5)6(C6H3ClNO2)2O]
  • M r = 1035.19
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00m99-efi1.jpg
  • a = 20.477 (2) Å
  • b = 9.6220 (11) Å
  • c = 22.513 (3) Å
  • β = 94.978 (2)°
  • V = 4419.0 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.39 mm−1
  • T = 298 (2) K
  • 0.45 × 0.26 × 0.19 mm

Data collection

  • Bruker SMART diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.567, T max = 0.770
  • 20773 measured reflections
  • 7764 independent reflections
  • 4921 reflections with I > 2σ(I)
  • R int = 0.083

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.135
  • S = 1.05
  • 7764 reflections
  • 532 parameters
  • H-atom parameters constrained
  • Δρmax = 2.07 e Å−3
  • Δρmin = −1.02 e Å−3

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: DIAMOND (Brandenburg, 1998 [triangle]); software used to prepare material for publication: SHELXL97.

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042335/bh2210sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042335/bh2210Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.)

Experimental

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

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

Figures

Fig. 1.
The molecular structure of the title compound, showing displacement ellipsoids at the 30% probability level.
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.

Crystal data

[Sb2(C6H5)6(C6H3ClNO2)2O]F(000) = 2056
Mr = 1035.19Dx = 1.556 Mg m3
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 mm1
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

Bruker SMART diffractometer7764 independent reflections
Radiation source: fine-focus sealed tube4921 reflections with I > 2σ(I)
graphiteRint = 0.083
[var phi] 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

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 = 1.05w = 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 Å3
0 restraintsΔρmin = −1.02 e Å3

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

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2210).

References

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

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