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

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ISSN: 2056-9890

catena-Poly[[di­phenyl­propyl­tin(IV)]-μ-chloro­acetato-κ2O:O′]

aDepartment of Chemistry, Shahid Beheshti University, Evin, Tehran 1983963113, Iran, and bSchool of Chemistry, University College of Science, University of Tehran, Tehran, Iran
*Correspondence e-mail: m-pouramini@cc.sbu.ac.ir

(Received 27 May 2008; accepted 2 July 2008; online 9 July 2008)

The title compound, [Sn(C3H7)(C6H5)2(C2H2ClO2)]n, comprises polymeric carboxyl­ate-bridged spiral chains with two monomer formula units in the asymmetric unit. Both Sn centres exhibit similar distorted trigonal–bipyramidal [C3SnO2] coordination, with the O atoms of the carboyxlate ligands in trans positions.

Related literature

For the structures of similar organotin compounds, see: Amini et al. (2002[Amini, M. M., Abadi, S. H., Mirzaee, M., Lügger, T., Hahn, F. E. & Ng, S. W. (2002). Acta Cryst. E58, m650-m652.], 2006[Amini, M. M., Alijani, V., Azadmeher, A., Khavasi, H. & Ng, S. W. (2006). Acta Cryst. E62, m2028-m2029.]); Ng et al. (1988[Ng, S. W., Chen, W. & Kumar Das, V. G. (1988). J. Organomet. Chem. 364, 59-64.]); Teo et al. (2004[Teo, Y. Y., Lo, K. M. & Ng, S. W. (2004). Acta Cryst. E60, m1478-m1480.]). The synthesis of the precursor diphenyl-n-propyl­tin(IV) iodide follows the procedure given by Snegur & Manulkin (1964[Snegur, L. N. & Manulkin, Z. M. (1964). Zh. Obshch. Khim. 34, 4030-4035.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C3H7)(C6H5)2(C2H2ClO2)]

  • Mr = 409.48

  • Orthorhombic, P c a 21

  • a = 19.330 (4) Å

  • b = 11.440 (2) Å

  • c = 16.390 (3) Å

  • V = 3624.4 (13) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.56 mm−1

  • T = 298 (2) K

  • 0.49 × 0.21 × 0.19 mm

Data collection
  • Stoe IPDSII diffractometer

  • Absorption correction: numerical [X-RED and X-SHAPE (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany.])] Tmin = 0.679, Tmax = 0.826

  • 13588 measured reflections

  • 8672 independent reflections

  • 7285 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.123

  • S = 1.11

  • 8672 reflections

  • 380 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.79 e Å−3

  • Δρmin = −0.55 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 3643 Friedel pairs

  • Flack parameter: −0.04 (4)

Table 1
Selected bond lengths (Å)

Sn1—C3 2.105 (9)
Sn1—C12 2.125 (7)
Sn1—C6 2.137 (7)
Sn1—O1 2.178 (4)
Sn1—O4i 2.478 (5)
Sn2—C29 2.129 (7)
Sn2—C23 2.130 (6)
Sn2—C20 2.130 (8)
Sn2—O3 2.190 (5)
Sn2—O2 2.469 (5)
Symmetry code: (i) [-x, -y, z-{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

This study continues our structural work on Sn compounds of carboxylic acid derivatives with mixed organic groups. Since the synthesis of these compounds (mixed organic groups on tin) is not always straightforward, only a few structures have been reported. For mixed aryl/alkyl carboxylates the structures of diphenylmethyltin (Amini et al., 2006), diphenylmethyltin (Amini et al., 2002) and diphenylcyclopentyltin (Teo et al., 2004) are known. For all these structures, the Sn centres are carboxylate-bridged (Ng et al., 1988). This structural motif is also realised in the title compound which consists of two independent molecules in the asymmetric unit (Fig. 1). The two molecules are linked via carboxylate O atoms to form polymeric spiral chains parallel to [001]. The distorted trigonal bipyrimidal [C3SnO2] coordination of the two Sn centers in the independent molecules is very similar, with one axial Sn—O bond being considerably longer ( 2.47 Å) than the other axial Sn—O bond ( 2.18 Å; Table 1).

Related literature top

For the structures of similar organotin compounds, see: Amini et al. (2002, 2006); Ng et al. (1988); Teo et al. (2004). The synthesis of the precursor diphenyl-n-propyltin(IV) iodide follows the procedure given by Snegur & Manulkin (1964).

Experimental top

Triphenyl-n-propyltin was prepared by using a conventional Grignard reaction based on triphenyltin chloride. The reagent was then treated with elemental iodine in order to cleave one of the three aromatic groups to yield diphenyl-n-propyltin(IV) iodide (Snegur & Manulkin, 1964). The latter (0.20 g, 0.45 mmol) was combined with silver monochloroacetate (0.09 g, 0.45 mmol) in methanol (10 ml), and the resulting AgI precipitate was removed by filtration. The solid obtained from concentration of the filtrate was purified by recrystallisation from a methanol–hexane (1:1 v/v) mixture to yield block-shaped, colorless crystals with an average size of about 0.3 mm (melting point 385 K).

Refinement top

The H atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and included in the refinement in the riding model approximation, with their displacement parameters set at 1.2 or 1.5 (propyl) times Ueq(C) of their parent atom.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound as a portion of the polymeric chain, showing the atom labelling scheme and displacement ellipsoids drawn at the 30% probability level.
catena-Poly[[diphenylpropyltin(IV)]-µ-chloroacetato-κ2O:O'] top
Crystal data top
[Sn(C3H7)(C6H5)2(C2H2ClO2)]F(000) = 1632
Mr = 409.48Dx = 1.501 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 7531 reflections
a = 19.330 (4) Åθ = 2.1–29.3°
b = 11.440 (2) ŵ = 1.56 mm1
c = 16.390 (3) ÅT = 298 K
V = 3624.4 (13) Å3Block, colourless
Z = 80.49 × 0.21 × 0.19 mm
Data collection top
Stoe IPDSII
diffractometer
7285 reflections with I > 2σ(I)
ω scansRint = 0.034
Absorption correction: numerical
[X-RED and X-SHAPE (Stoe & Cie, 2005)]
θmax = 29.3°, θmin = 2.1°
Tmin = 0.679, Tmax = 0.826h = 2619
13588 measured reflectionsk = 1115
8672 independent reflectionsl = 2220
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0589P)2 + 2.5701P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.045(Δ/σ)max = 0.026
wR(F2) = 0.123Δρmax = 0.79 e Å3
S = 1.12Δρmin = 0.55 e Å3
8672 reflectionsAbsolute structure: Flack (1983), with 3643 Friedel pairs
380 parametersAbsolute structure parameter: 0.04 (4)
1 restraint
Crystal data top
[Sn(C3H7)(C6H5)2(C2H2ClO2)]V = 3624.4 (13) Å3
Mr = 409.48Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 19.330 (4) ŵ = 1.56 mm1
b = 11.440 (2) ÅT = 298 K
c = 16.390 (3) Å0.49 × 0.21 × 0.19 mm
Data collection top
Stoe IPDSII
diffractometer
8672 independent reflections
Absorption correction: numerical
[X-RED and X-SHAPE (Stoe & Cie, 2005)]
7285 reflections with I > 2σ(I)
Tmin = 0.679, Tmax = 0.826Rint = 0.034
13588 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.123Δρmax = 0.79 e Å3
S = 1.12Δρmin = 0.55 e Å3
8672 reflectionsAbsolute structure: Flack (1983), with 3643 Friedel pairs
380 parametersAbsolute structure parameter: 0.04 (4)
1 restraint
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.116980 (19)0.14033 (4)0.14385 (3)0.06080 (11)
Sn20.069248 (18)0.19052 (3)0.10089 (3)0.05654 (10)
Cl10.31159 (9)0.0258 (3)0.04475 (13)0.0973 (7)
Cl20.0078 (3)0.5469 (3)0.2698 (3)0.181 (2)
O10.1911 (2)0.0768 (5)0.0541 (3)0.0688 (11)
O20.1179 (2)0.0422 (4)0.0078 (3)0.0610 (10)
O30.0358 (3)0.3316 (5)0.1821 (3)0.0735 (13)
O40.0384 (3)0.2223 (5)0.2512 (3)0.0693 (12)
C10.1739 (3)0.0072 (6)0.0016 (4)0.0560 (13)
C20.2274 (4)0.0195 (8)0.0668 (5)0.084 (2)
H2A0.21290.01750.11720.1*
H2B0.22790.10320.0760.1*
C30.0926 (6)0.0203 (9)0.1995 (7)0.102 (3)
H3A0.06750.00520.24970.123*
H3B0.06220.0640.16360.123*
C40.1574 (7)0.0968 (12)0.2194 (9)0.104 (4)
H4B0.17970.11870.16860.149*
H4A0.190.05010.25040.149*
C50.1422 (12)0.1986 (18)0.2636 (13)0.110 (10)
H5A0.15290.18630.32020.301*
H5B0.16940.26230.2430.301*
H5C0.0940.21670.2580.301*
C60.1961 (3)0.2438 (6)0.1993 (4)0.0638 (14)
C70.2427 (5)0.3094 (6)0.1541 (8)0.085 (2)
H70.24040.30740.09750.102*
C80.2919 (5)0.3771 (8)0.1913 (7)0.097 (3)
H80.32190.42160.15970.117*
C90.2973 (6)0.3797 (9)0.2740 (8)0.109 (4)
H90.33010.42710.29910.131*
C100.2531 (7)0.3105 (12)0.3208 (7)0.119 (4)
H100.25830.30790.37720.143*
C110.2017 (5)0.2460 (9)0.2835 (5)0.089 (2)
H110.17060.20360.31520.106*
C120.0543 (4)0.2221 (7)0.0539 (4)0.0657 (16)
C130.0797 (4)0.3076 (9)0.0027 (6)0.089 (3)
H130.12590.32970.00650.107*
C140.0377 (6)0.3603 (10)0.0536 (6)0.104 (3)
H140.05580.41890.08670.125*
C150.0302 (7)0.3290 (12)0.0625 (8)0.115 (4)
H150.05780.36520.10150.138*
C160.0567 (5)0.2440 (12)0.0135 (9)0.113 (3)
H160.10270.22150.01960.136*
C170.0146 (4)0.1885 (8)0.0475 (6)0.086 (2)
H170.0330.13170.08190.103*
C180.0086 (4)0.3153 (7)0.2375 (5)0.0694 (17)
C190.0275 (7)0.4147 (9)0.2922 (7)0.115 (4)
H19A0.01410.39420.34740.138*
H19B0.07740.42290.29160.138*
C200.0249 (4)0.1638 (9)0.0359 (7)0.111 (2)
H20A0.01380.12390.01460.109*
H20B0.05350.11140.06790.109*
C210.0660 (8)0.2664 (17)0.0160 (15)0.100 (10)
H21B0.10110.23780.02130.24*
H21A0.09020.28520.06610.24*
C220.0485 (13)0.3780 (15)0.0125 (16)0.114 (12)
H22A0.08980.42460.01700.269*
H22B0.01840.41630.02620.269*
H22C0.02520.37250.06410.269*
C230.1495 (4)0.2993 (6)0.0543 (5)0.0678 (16)
C240.1565 (7)0.3199 (12)0.0289 (6)0.114 (4)
H240.12390.290.06510.137*
C250.2113 (8)0.3843 (15)0.0583 (9)0.113 (6)
H250.21390.40120.11370.183*
C260.2619 (6)0.4234 (12)0.0071 (9)0.110 (4)
H260.30020.46240.02790.156*
C270.2559 (5)0.4052 (9)0.0734 (7)0.111 (4)
H270.290.4330.10850.133*
C280.1991 (4)0.3451 (6)0.1053 (7)0.087 (2)
H280.19480.3360.16150.105*
C290.0973 (4)0.0755 (8)0.1974 (5)0.0716 (19)
C300.0815 (6)0.0416 (9)0.1932 (7)0.107 (4)
H300.05830.07160.14820.128*
C310.1009 (9)0.1152 (15)0.2576 (11)0.117 (8)
H310.08920.1940.25550.188*
C320.1358 (9)0.0744 (19)0.3219 (9)0.107 (8)
H320.14880.12510.36350.188*
C330.1525 (7)0.0414 (16)0.3269 (6)0.113 (5)
H330.17750.06910.37140.159*
C340.1322 (5)0.1175 (11)0.2659 (5)0.099 (3)
H340.14180.19690.27050.119*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.05910 (19)0.0703 (2)0.05297 (19)0.00035 (18)0.0032 (2)0.0007 (2)
Sn20.05046 (16)0.0652 (2)0.05397 (19)0.00106 (16)0.00380 (19)0.0087 (2)
Cl10.0545 (8)0.165 (2)0.0727 (11)0.0156 (11)0.0042 (8)0.0015 (12)
Cl20.304 (6)0.099 (2)0.140 (3)0.048 (3)0.074 (4)0.015 (2)
O10.061 (2)0.085 (3)0.060 (2)0.005 (2)0.007 (2)0.018 (2)
O20.051 (2)0.070 (3)0.062 (2)0.0060 (19)0.0063 (19)0.011 (2)
O30.078 (3)0.074 (3)0.068 (3)0.006 (2)0.022 (3)0.000 (2)
O40.064 (3)0.079 (3)0.065 (3)0.006 (2)0.018 (2)0.004 (2)
C10.049 (3)0.065 (3)0.054 (3)0.002 (2)0.000 (2)0.004 (3)
C20.058 (3)0.111 (6)0.082 (4)0.017 (4)0.017 (3)0.032 (4)
C30.115 (7)0.094 (6)0.098 (6)0.014 (5)0.038 (6)0.024 (5)
C40.121 (9)0.122 (9)0.129 (10)0.007 (7)0.020 (7)0.025 (8)
C50.12 (2)0.169 (16)0.193 (19)0.012 (15)0.064 (18)0.072 (15)
C60.060 (3)0.068 (4)0.063 (3)0.004 (3)0.003 (3)0.007 (3)
C70.087 (5)0.088 (4)0.081 (5)0.009 (4)0.009 (5)0.009 (5)
C80.083 (5)0.087 (6)0.122 (8)0.008 (4)0.023 (5)0.003 (5)
C90.095 (6)0.096 (7)0.137 (10)0.007 (5)0.031 (7)0.038 (7)
C100.114 (8)0.156 (11)0.087 (7)0.003 (8)0.014 (6)0.046 (7)
C110.097 (6)0.112 (7)0.058 (4)0.001 (5)0.012 (4)0.013 (4)
C120.061 (3)0.083 (4)0.053 (3)0.005 (3)0.002 (3)0.003 (3)
C130.071 (4)0.125 (8)0.072 (5)0.006 (5)0.001 (4)0.022 (5)
C140.116 (8)0.110 (7)0.086 (6)0.009 (6)0.003 (6)0.031 (5)
C150.105 (8)0.143 (10)0.098 (7)0.012 (7)0.031 (6)0.014 (7)
C160.078 (5)0.120 (8)0.141 (10)0.002 (6)0.034 (6)0.002 (8)
C170.069 (4)0.094 (5)0.095 (6)0.009 (4)0.005 (4)0.008 (5)
C180.072 (4)0.076 (4)0.061 (4)0.006 (3)0.012 (3)0.003 (3)
C190.110 (10)0.080 (5)0.104 (7)0.004 (6)0.058 (7)0.008 (5)
C200.092 (4)0.108 (6)0.102 (6)0.000 (4)0.022 (4)0.004 (5)
C210.105 (12)0.119 (14)0.20 (3)0.001 (10)0.0207 (14)0.090 (17)
C220.12 (2)0.117 (12)0.30 (3)0.018 (13)0.09 (2)0.089 (16)
C230.061 (3)0.069 (4)0.074 (4)0.009 (3)0.017 (3)0.008 (3)
C240.113 (7)0.160 (11)0.070 (5)0.055 (7)0.017 (5)0.004 (6)
C250.160 (12)0.180 (13)0.117 (10)0.073 (11)0.054 (9)0.021 (9)
C260.103 (7)0.125 (9)0.163 (12)0.044 (7)0.047 (8)0.009 (8)
C270.093 (6)0.103 (6)0.137 (10)0.046 (5)0.005 (6)0.006 (6)
C280.090 (5)0.080 (4)0.092 (5)0.026 (3)0.009 (5)0.009 (5)
C290.060 (3)0.091 (5)0.064 (4)0.019 (3)0.015 (3)0.017 (4)
C300.125 (8)0.093 (6)0.102 (7)0.047 (6)0.046 (6)0.028 (5)
C310.120 (14)0.143 (12)0.148 (13)0.086 (11)0.079 (12)0.083 (11)
C320.166 (13)0.206 (17)0.099 (9)0.105 (13)0.055 (9)0.074 (10)
C330.111 (8)0.215 (16)0.072 (6)0.054 (10)0.012 (5)0.033 (8)
C340.090 (5)0.147 (9)0.060 (5)0.026 (6)0.010 (4)0.020 (5)
Geometric parameters (Å, º) top
Sn1—C32.105 (9)C13—H130.93
Sn1—C122.125 (7)C14—C151.368 (17)
Sn1—C62.137 (7)C14—H140.93
Sn1—O12.178 (4)C15—C161.362 (17)
Sn1—O4i2.478 (5)C15—H150.93
Sn2—C292.129 (7)C16—C171.437 (14)
Sn2—C232.130 (6)C16—H160.93
Sn2—C202.130 (8)C17—H170.93
Sn2—O32.190 (5)C18—C191.493 (12)
Sn2—O22.469 (5)C19—H19A0.97
Cl1—C21.746 (7)C19—H19B0.97
Cl2—C191.699 (11)C20—C211.455 (17)
O1—C11.257 (8)C20—H20A0.97
O2—C11.224 (7)C20—H20B0.97
O3—C181.264 (9)C21—C221.40 (3)
O4—C181.231 (9)C21—H21B0.97
O4—Sn1ii2.478 (5)C21—H21A0.97
C1—C21.518 (9)C22—H22A0.96
C2—H2A0.97C22—H22B0.96
C2—H2B0.97C22—H22C0.96
C3—C41.562 (16)C23—C281.376 (12)
C3—H3A0.97C23—C241.392 (12)
C3—H3B0.97C24—C251.376 (15)
C4—C51.40 (2)C24—H240.93
C4—H4B0.97C25—C261.36 (2)
C4—H4A0.97C25—H250.93
C5—H5A0.96C26—C271.342 (16)
C5—H5B0.96C26—H260.93
C5—H5C0.96C27—C281.396 (12)
C6—C111.384 (10)C27—H270.93
C6—C71.387 (12)C28—H280.93
C7—C81.370 (13)C29—C301.375 (14)
C7—H70.93C29—C341.394 (14)
C8—C91.360 (17)C30—C311.401 (16)
C8—H80.93C30—H300.93
C9—C101.394 (18)C31—C321.34 (3)
C9—H90.93C31—H310.93
C10—C111.381 (15)C32—C331.37 (2)
C10—H100.93C32—H320.93
C11—H110.93C33—C341.383 (15)
C12—C131.378 (12)C33—H330.93
C12—C171.391 (11)C34—H340.93
C13—C141.370 (14)
C3—Sn1—C12123.9 (4)C15—C14—C13121.6 (10)
C3—Sn1—C6117.4 (4)C15—C14—H14119.2
C12—Sn1—C6117.3 (3)C13—C14—H14119.2
C3—Sn1—O198.6 (3)C16—C15—C14119.1 (10)
C12—Sn1—O193.0 (2)C16—C15—H15120.5
C6—Sn1—O190.1 (2)C14—C15—H15120.5
C3—Sn1—O4i83.8 (3)C15—C16—C17120.9 (10)
C12—Sn1—O4i88.0 (2)C15—C16—H16119.6
C6—Sn1—O4i86.2 (2)C17—C16—H16119.6
O1—Sn1—O4i176.21 (18)C12—C17—C16118.2 (9)
C29—Sn2—C23116.2 (3)C12—C17—H17120.9
C29—Sn2—C20120.0 (4)C16—C17—H17120.9
C23—Sn2—C20121.8 (4)O4—C18—O3125.3 (7)
C29—Sn2—O394.5 (3)O4—C18—C19115.7 (7)
C23—Sn2—O390.1 (2)O3—C18—C19119.0 (8)
C20—Sn2—O399.1 (3)C18—C19—Cl2116.7 (7)
C29—Sn2—O286.4 (2)C18—C19—H19A108.1
C23—Sn2—O284.4 (2)Cl2—C19—H19A108.1
C20—Sn2—O285.3 (3)C18—C19—H19B108.1
O3—Sn2—O2174.26 (18)Cl2—C19—H19B108.1
C1—O1—Sn1121.9 (4)H19A—C19—H19B107.3
C1—O2—Sn2134.8 (4)C21—C20—Sn2117.6 (9)
C18—O3—Sn2121.9 (5)C21—C20—H20A107.7
C18—O4—Sn1ii137.8 (5)Sn2—C20—H20A107.9
O2—C1—O1125.9 (6)C21—C20—H20B108
O2—C1—C2116.8 (6)Sn2—C20—H20B107.9
O1—C1—C2117.3 (5)H20A—C20—H20B107.2
C1—C2—Cl1115.5 (5)C22—C21—C20132.7 (16)
C1—C2—H2A108.4C22—C21—H21B104.8
Cl1—C2—H2A108.4C20—C21—H21B104.8
C1—C2—H2B108.4C22—C21—H21A101.0
Cl1—C2—H2B108.4C20—C21—H21A104.5
H2A—C2—H2B107.5H21B—C21—H21A105.7
C4—C3—Sn1113.6 (8)C21—C22—H22A109.2
C4—C3—H3A108.8C21—C22—H22B109.6
Sn1—C3—H3A108.9H22A—C22—H22B107.0
C4—C3—H3B108.9C21—C22—H22C109.6
Sn1—C3—H3B108.9H22A—C22—H22C111.0
H3A—C3—H3B107.7H22B—C22—H22C109.5
C5—C4—C3113.9 (13)C28—C23—C24117.6 (8)
C5—C4—H4B108.8C28—C23—Sn2120.9 (6)
C3—C4—H4B108.8C24—C23—Sn2121.4 (6)
C5—C4—H4A108.8C25—C24—C23120.5 (11)
C3—C4—H4A108.8C25—C24—H24119.7
H4B—C4—H4A107.7C23—C24—H24119.7
C4—C5—H5A109.5C26—C25—C24120.8 (12)
C4—C5—H5B109.4C26—C25—H25119.6
H5A—C5—H5B109.5C24—C25—H25119.6
C4—C5—H5C109.5C27—C26—C25119.5 (9)
H5A—C5—H5C109.5C27—C26—H26120.3
H5B—C5—H5C109.5C25—C26—H26120.2
C11—C6—C7118.1 (8)C26—C27—C28120.8 (11)
C11—C6—Sn1119.4 (6)C26—C27—H27119.6
C7—C6—Sn1122.5 (6)C28—C27—H27119.6
C8—C7—C6121.3 (11)C23—C28—C27120.6 (10)
C8—C7—H7119.4C23—C28—H28119.7
C6—C7—H7119.4C27—C28—H28119.7
C9—C8—C7120.6 (11)C30—C29—C34118.9 (9)
C9—C8—H8119.7C30—C29—Sn2120.6 (7)
C7—C8—H8119.7C34—C29—Sn2120.5 (7)
C8—C9—C10119.2 (10)C29—C30—C31119.2 (15)
C8—C9—H9120.4C29—C30—H30120.4
C10—C9—H9120.4C31—C30—H30120.4
C11—C10—C9120.1 (10)C32—C31—C30121.3 (17)
C11—C10—H10119.9C32—C31—H31119.3
C9—C10—H10120C30—C31—H31119.4
C10—C11—C6120.5 (10)C31—C32—C33120.4 (12)
C10—C11—H11119.8C31—C32—H32119.9
C6—C11—H11119.7C33—C32—H32119.8
C13—C12—C17119.5 (8)C32—C33—C34120.0 (14)
C13—C12—Sn1122.1 (6)C32—C33—H33120
C17—C12—Sn1118.4 (6)C34—C33—H33120
C14—C13—C12120.8 (9)C33—C34—C29120.1 (13)
C14—C13—H13119.6C33—C34—H34120
C12—C13—H13119.6C29—C34—H34119.9
C3—Sn1—O1—C163.3 (6)C14—C15—C16—C171 (2)
C12—Sn1—O1—C161.6 (6)C13—C12—C17—C160.8 (14)
C6—Sn1—O1—C1178.9 (5)Sn1—C12—C17—C16179.9 (8)
C29—Sn2—O2—C155.1 (6)C15—C16—C17—C121.5 (18)
C23—Sn2—O2—C161.7 (6)Sn1ii—O4—C18—O3172.1 (5)
C20—Sn2—O2—C1175.6 (7)Sn1ii—O4—C18—C197.7 (13)
C29—Sn2—O3—C1854.2 (6)Sn2—O3—C18—O41.5 (11)
C23—Sn2—O3—C18170.5 (6)Sn2—O3—C18—C19178.3 (8)
C20—Sn2—O3—C1867.2 (7)O4—C18—C19—Cl2175.0 (8)
Sn2—O2—C1—O1175.3 (5)O3—C18—C19—Cl25.2 (15)
Sn2—O2—C1—C24.0 (10)C29—Sn2—C20—C21138.4 (13)
Sn1—O1—C1—O28.1 (10)C23—Sn2—C20—C2158.1 (14)
Sn1—O1—C1—C2172.6 (5)O3—Sn2—C20—C2137.7 (14)
O2—C1—C2—Cl1166.5 (6)O2—Sn2—C20—C21138.5 (14)
O1—C1—C2—Cl112.8 (10)Sn2—C20—C21—C2245 (4)
C12—Sn1—C3—C4145.3 (8)C29—Sn2—C23—C2836.4 (7)
C6—Sn1—C3—C448.8 (10)C20—Sn2—C23—C28159.5 (6)
O1—Sn1—C3—C445.7 (9)O3—Sn2—C23—C2858.7 (7)
O4i—Sn1—C3—C4131.3 (9)O2—Sn2—C23—C28119.6 (7)
Sn1—C3—C4—C5174.0 (13)C29—Sn2—C23—C24139.1 (9)
C3—Sn1—C6—C1136.3 (8)C20—Sn2—C23—C2425.0 (10)
C12—Sn1—C6—C11130.5 (7)O3—Sn2—C23—C24125.7 (9)
O1—Sn1—C6—C11136.0 (7)O2—Sn2—C23—C2455.9 (9)
O4i—Sn1—C6—C1144.7 (7)C28—C23—C24—C250 (2)
C3—Sn1—C6—C7143.5 (6)Sn2—C23—C24—C25175.8 (12)
C12—Sn1—C6—C749.6 (7)C23—C24—C25—C264 (3)
O1—Sn1—C6—C743.9 (6)C24—C25—C26—C274 (3)
O4i—Sn1—C6—C7135.4 (6)C25—C26—C27—C281 (2)
C11—C6—C7—C81.6 (12)C24—C23—C28—C273.0 (14)
Sn1—C6—C7—C8178.5 (7)Sn2—C23—C28—C27172.7 (8)
C6—C7—C8—C91.4 (14)C26—C27—C28—C232.6 (17)
C7—C8—C9—C101.5 (17)C23—Sn2—C29—C30129.2 (6)
C8—C9—C10—C114.1 (18)C20—Sn2—C29—C3035.2 (7)
C9—C10—C11—C63.8 (18)O3—Sn2—C29—C30138.5 (6)
C7—C6—C11—C101.0 (14)O2—Sn2—C29—C3047.2 (6)
Sn1—C6—C11—C10178.9 (8)C23—Sn2—C29—C3450.7 (7)
C3—Sn1—C12—C13161.3 (7)C20—Sn2—C29—C34144.9 (7)
C6—Sn1—C12—C1332.7 (8)O3—Sn2—C29—C3441.7 (6)
O1—Sn1—C12—C1358.9 (7)O2—Sn2—C29—C34132.6 (6)
O4i—Sn1—C12—C13117.4 (7)C34—C29—C30—C310.0 (13)
C3—Sn1—C12—C1719.4 (8)Sn2—C29—C30—C31179.8 (8)
C6—Sn1—C12—C17146.6 (6)C29—C30—C31—C321.7 (18)
O1—Sn1—C12—C17121.8 (7)C30—C31—C32—C331 (2)
O4i—Sn1—C12—C1761.9 (7)C31—C32—C33—C341 (2)
C17—C12—C13—C140.6 (15)C32—C33—C34—C292.8 (16)
Sn1—C12—C13—C14178.7 (8)C30—C29—C34—C332.3 (13)
C12—C13—C14—C151.3 (18)Sn2—C29—C34—C33177.6 (7)
C13—C14—C15—C161 (2)
Symmetry codes: (i) x, y, z1/2; (ii) x, y, z+1/2.

Experimental details

Crystal data
Chemical formula[Sn(C3H7)(C6H5)2(C2H2ClO2)]
Mr409.48
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)298
a, b, c (Å)19.330 (4), 11.440 (2), 16.390 (3)
V3)3624.4 (13)
Z8
Radiation typeMo Kα
µ (mm1)1.56
Crystal size (mm)0.49 × 0.21 × 0.19
Data collection
DiffractometerStoe IPDSII
diffractometer
Absorption correctionNumerical
[X-RED and X-SHAPE (Stoe & Cie, 2005)]
Tmin, Tmax0.679, 0.826
No. of measured, independent and
observed [I > 2σ(I)] reflections
13588, 8672, 7285
Rint0.034
(sin θ/λ)max1)0.687
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.123, 1.12
No. of reflections8672
No. of parameters380
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.79, 0.55
Absolute structureFlack (1983), with 3643 Friedel pairs
Absolute structure parameter0.04 (4)

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top
Sn1—C32.105 (9)Sn2—C292.129 (7)
Sn1—C122.125 (7)Sn2—C232.130 (6)
Sn1—C62.137 (7)Sn2—C202.130 (8)
Sn1—O12.178 (4)Sn2—O32.190 (5)
Sn1—O4i2.478 (5)Sn2—O22.469 (5)
Symmetry code: (i) x, y, z1/2.
 

Acknowledgements

The authors acknowledge Shahid Beheshti University and Tehran University for financial support.

References

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