metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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

(Received 15 November 2008; accepted 12 December 2008; online 20 December 2008)

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[Ferguson, G. & Ridley, D. R. (1973). Acta Cryst. B29, 2221-2226.]); Preut et al. (1985[Preut, H., Rüther, R. & Huber, F. (1985). Acta Cryst. C41, 358-360.], 1986[Preut, H., Rüther, R. & Huber, F. (1986). Acta Cryst. C42, 1154-1157.]).

[Scheme 1]

Experimental

Crystal data
  • [Sb2(C6H5)6(C6H3ClNO2)2O]

  • Mr = 1035.19

  • Monoclinic, P 21 /n

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.567, Tmax = 0.770

  • 20773 measured reflections

  • 7764 independent reflections

  • 4921 reflections with I > 2σ(I)

  • Rint = 0.083

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 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

Table 1
Selected geometric parameters (Å, °)

Sb1—O1 1.955 (5)
Sb1—O2 2.208 (5)
Sb2—O1 1.955 (5)
Sb2—O4 2.229 (5)
O1—Sb1—O2 179.2 (2)
O1—Sb2—O4 174.6 (2)
Sb1—O1—Sb2 165.1 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C17—H17⋯N2i 0.93 2.66 3.556 (14) 163
C39—H39⋯O5ii 0.93 2.63 3.544 (12) 167
C23—H23⋯O3iii 0.93 2.37 3.166 (12) 144
C23—H23⋯O3iii 0.93 2.37 3.166 (12) 144
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x, y+1, z; (iii) x, y-1, z.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Ctyst. A63, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Ctyst. A63, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. University of Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


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 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 top
Bruker SMART
diffractometer
7764 independent reflections
Radiation source: fine-focus sealed tube4921 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.083
ϕ and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2024
Tmin = 0.567, Tmax = 0.770k = 1011
20773 measured reflectionsl = 1726
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 Å3
0 restraintsΔρmin = 1.02 e Å3
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 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 1.05Δρmax = 2.07 e Å3
7764 reflectionsΔρmin = 1.02 e Å3
532 parameters
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)
H60.21240.47200.06670.114*
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)
H100.77350.36230.38630.095*
C110.7982 (6)0.4250 (14)0.4703 (6)0.112 (5)
H110.84000.45640.46390.135*
C120.7765 (6)0.4336 (13)0.5256 (6)0.098 (4)
H120.80460.46960.55650.117*
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)
H210.45170.20610.01450.112*
C220.4396 (5)0.3254 (13)0.0847 (8)0.098 (5)
H220.44010.40890.06400.118*
C230.4317 (5)0.3272 (11)0.1441 (7)0.093 (4)
H230.42600.41070.16380.112*
C240.4322 (4)0.2014 (9)0.1747 (5)0.069 (3)
H240.42730.19970.21540.082*
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)
H340.75940.13060.16520.120*
C350.6649 (6)0.1646 (11)0.1715 (5)0.086 (3)
H350.65730.20930.13490.103*
C360.6140 (4)0.1501 (9)0.2084 (4)0.064 (3)
H360.57260.18560.19690.077*
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)
H440.40810.07160.33310.088*
C450.3699 (5)0.2554 (13)0.3558 (5)0.088 (4)
H450.32710.22360.35670.105*
C460.3837 (5)0.3904 (12)0.3687 (5)0.080 (3)
H460.35060.45100.37780.096*
C470.4452 (5)0.4351 (10)0.3680 (5)0.082 (3)
H470.45510.52720.37770.099*
C480.4944 (4)0.3475 (9)0.3532 (4)0.067 (3)
H480.53690.38120.35250.080*
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, º) 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, º) 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, y1, z.

Experimental details

Crystal data
Chemical formula[Sb2(C6H5)6(C6H3ClNO2)2O]
Mr1035.19
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)20.477 (2), 9.6220 (11), 22.513 (3)
β (°) 94.978 (2)
V3)4419.0 (9)
Z4
Radiation typeMo Kα
µ (mm1)1.39
Crystal size (mm)0.45 × 0.26 × 0.19
Data collection
DiffractometerBruker SMART
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.567, 0.770
No. of measured, independent and
observed [I > 2σ(I)] reflections
20773, 7764, 4921
Rint0.083
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.135, 1.05
No. of reflections7764
No. of parameters532
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)2.07, 1.02

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1998).

Selected geometric parameters (Å, º) 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)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17···N2i0.932.663.556 (14)162.8
C39—H39···O5ii0.932.633.544 (12)166.9
C23—H23···O3iii0.932.373.166 (12)143.7
C23—H23···O3iii0.932.373.166 (12)143.7
Symmetry codes: (i) x+1, y, z+1; (ii) x, y+1, z; (iii) x, y1, z.
 

Acknowledgements

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

References

First citationBrandenburg, K. (1998). DIAMOND. University of Bonn, Germany.  Google Scholar
First citationFerguson, G. & Ridley, D. R. (1973). Acta Cryst. B29, 2221–2226.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
First citationPreut, H., Rüther, R. & Huber, F. (1985). Acta Cryst. C41, 358–360.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationPreut, H., Rüther, R. & Huber, F. (1986). Acta Cryst. C42, 1154–1157.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Ctyst. A63, 112-122.  Web of Science CrossRef Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar

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