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

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Di­chloridobis(1,3-phenyl­propane-1,3-dionato-κ2O,O′)tin(IV) toluene hemisolvate

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 13 July 2010; accepted 14 July 2010; online 21 July 2010)

The two Sn—O—C—C—C—O chelate rings in the title compound, [Sn(C15H11O2)2Cl2]·0.5C7H8, adopt envelope conformations, with the Sn atom deviating from the least-squares plane passing through the C and O atoms by 0.626 (1) Å in one ring and by 0.690 (1) Å for the other. The two planes are aligned at an angle of 59.6 (1)°. The Cl atoms occupy cis positions in the octa­hedral SnCl2O4 coordination environment. The solvent mol­ecule is disordered about a center of inversion.

Related literature

For the crystal structure of anhydrous dichloro­dibis(1,3-phenyl­propane-1,3-dionato)tin(IV), see: Searle et al. (1989[Searle, D., Smith, P. J., Bell, N. A., March, L. A., Nowell, I. W. & Donaldson, J. D. (1989). Inorg. Chim. Acta, 162, 143-149.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C15H11O2)2Cl2]·0.5C7H8

  • Mr = 682.13

  • Monoclinic, P 21 /n

  • a = 8.0024 (1) Å

  • b = 21.5554 (2) Å

  • c = 16.6838 (2) Å

  • β = 97.2740 (5)°

  • V = 2854.71 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.12 mm−1

  • T = 100 K

  • 0.40 × 0.35 × 0.30 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.663, Tmax = 0.730

  • 23143 measured reflections

  • 6534 independent reflections

  • 6269 reflections with I > 2σ(I)

  • Rint = 0.014

Refinement
  • R[F2 > 2σ(F2)] = 0.018

  • wR(F2) = 0.049

  • S = 1.02

  • 6534 reflections

  • 386 parameters

  • 43 restraints

  • H-atom parameters constrained

  • Δρmax = 0.51 e Å−3

  • Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The toluene solvate (Scheme I) was obtained from the reaction of dibenzyltin dichloride and dibenzoylmethane in ethanol. Since no toluene was used in the synthesis, the toluene in the crystal structure would have resulted from the cleavage of the tin–carbonbenzyl bond by the dibenzoylmethane molecule, which in the deprotonated form chelates to tin (Fig. 1). The six-membered Sn–O–C–C–C–O chelate rings adopt an envelope-shaped conformation, with the tin atom lying off the least-squares plane defined by the carbon/oxygen atoms. Bond dimensions are similar to those reported for the anhydrous compound (Searle et al., 1989).

Related literature top

For the crystal structure of anhydrous dichlorodibis(1,3-phenylpropane-1,3-dionato)tin, see: Searle et al. (1989).

Experimental top

Dibenzyltin dichloride (1 mmol) and dibenzoylmethane (1 mmol) were refluxed in ethanol for 1 h. The toluene solvate was obtained as crystals when the solvent was allowed to evaporate.

Refinement top

The toluene molecule is disordered over a center-of-inversion. The aromatic ring was refined as a hexagon of 1.39 Å sides, and the Cmethyl–Cphenyl distance was refined with a distance restraint of 1.54±0.01 Å; the displacement parameters of the seven carbon atoms were restrained to be nearly isotropic.

Hydrogen atoms were placed in calculated positions (C–H 0.95–0.98 Å) and included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C).

Structure description top

The toluene solvate (Scheme I) was obtained from the reaction of dibenzyltin dichloride and dibenzoylmethane in ethanol. Since no toluene was used in the synthesis, the toluene in the crystal structure would have resulted from the cleavage of the tin–carbonbenzyl bond by the dibenzoylmethane molecule, which in the deprotonated form chelates to tin (Fig. 1). The six-membered Sn–O–C–C–C–O chelate rings adopt an envelope-shaped conformation, with the tin atom lying off the least-squares plane defined by the carbon/oxygen atoms. Bond dimensions are similar to those reported for the anhydrous compound (Searle et al., 1989).

For the crystal structure of anhydrous dichlorodibis(1,3-phenylpropane-1,3-dionato)tin, see: Searle et al. (1989).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of SnCl2(C15H11O2).0.5C7H8 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Dichloridobis(1,3-phenylpropane-1,3-dionato-κ2O,O')tin(IV) toluene hemisolvate top
Crystal data top
[Sn(C15H11O2)2Cl2]·0.5C7H8F(000) = 1372
Mr = 682.13Dx = 1.587 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9775 reflections
a = 8.0024 (1) Åθ = 2.6–28.3°
b = 21.5554 (2) ŵ = 1.12 mm1
c = 16.6838 (2) ÅT = 100 K
β = 97.2740 (5)°Block, colorless
V = 2854.71 (6) Å30.40 × 0.35 × 0.30 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
6534 independent reflections
Radiation source: fine-focus sealed tube6269 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.663, Tmax = 0.730k = 2827
23143 measured reflectionsl = 2120
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)] = 0.018Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.049H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0264P)2 + 1.8695P]
where P = (Fo2 + 2Fc2)/3
6534 reflections(Δ/σ)max = 0.001
386 parametersΔρmax = 0.51 e Å3
43 restraintsΔρmin = 0.48 e Å3
Crystal data top
[Sn(C15H11O2)2Cl2]·0.5C7H8V = 2854.71 (6) Å3
Mr = 682.13Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.0024 (1) ŵ = 1.12 mm1
b = 21.5554 (2) ÅT = 100 K
c = 16.6838 (2) Å0.40 × 0.35 × 0.30 mm
β = 97.2740 (5)°
Data collection top
Bruker SMART APEX
diffractometer
6534 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
6269 reflections with I > 2σ(I)
Tmin = 0.663, Tmax = 0.730Rint = 0.014
23143 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.01843 restraints
wR(F2) = 0.049H-atom parameters constrained
S = 1.02Δρmax = 0.51 e Å3
6534 reflectionsΔρmin = 0.48 e Å3
386 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.423028 (11)0.234239 (4)0.547401 (5)0.01263 (4)
Cl10.20470 (4)0.170342 (15)0.48111 (2)0.01801 (7)
Cl20.23181 (4)0.308712 (15)0.58666 (2)0.01822 (7)
O10.62198 (12)0.28585 (4)0.60498 (6)0.01569 (18)
O20.43258 (12)0.18534 (4)0.65338 (6)0.01634 (19)
O30.59905 (12)0.17245 (4)0.51420 (6)0.01660 (19)
O40.45921 (13)0.28244 (4)0.44524 (6)0.01604 (19)
C10.74806 (17)0.35237 (6)0.70667 (8)0.0146 (2)
C20.87260 (18)0.37017 (7)0.65982 (9)0.0187 (3)
H20.88710.34760.61230.022*
C30.97545 (18)0.42080 (7)0.68234 (9)0.0219 (3)
H31.06150.43210.65080.026*
C40.95274 (18)0.45488 (7)0.75081 (9)0.0209 (3)
H41.02230.48980.76580.025*
C50.82797 (19)0.43778 (7)0.79729 (9)0.0199 (3)
H50.81140.46130.84380.024*
C60.72730 (18)0.38632 (6)0.77598 (8)0.0176 (3)
H60.64400.37420.80870.021*
C70.63927 (16)0.29790 (6)0.68135 (8)0.0142 (2)
C80.56859 (18)0.26349 (6)0.73948 (8)0.0160 (3)
H80.58580.27820.79360.019*
C90.47456 (16)0.20909 (6)0.72458 (8)0.0142 (2)
C100.41507 (17)0.17367 (6)0.79168 (8)0.0153 (2)
C110.42603 (19)0.19764 (7)0.87008 (9)0.0208 (3)
H110.48110.23610.88250.025*
C120.3567 (2)0.16530 (8)0.92983 (9)0.0257 (3)
H120.36180.18230.98260.031*
C130.2798 (2)0.10820 (8)0.91288 (10)0.0259 (3)
H130.23280.08620.95400.031*
C140.27184 (19)0.08334 (7)0.83542 (10)0.0230 (3)
H140.22130.04390.82390.028*
C150.33758 (18)0.11603 (6)0.77509 (9)0.0183 (3)
H150.33000.09920.72210.022*
C160.62450 (16)0.16168 (6)0.44027 (8)0.0146 (2)
C170.70704 (16)0.10122 (6)0.42799 (8)0.0153 (3)
C180.67625 (18)0.05155 (6)0.47798 (9)0.0182 (3)
H180.60840.05760.52010.022*
C190.74452 (19)0.00663 (7)0.46630 (9)0.0225 (3)
H190.72170.04040.49980.027*
C200.84583 (19)0.01515 (7)0.40570 (10)0.0243 (3)
H200.89250.05490.39780.029*
C210.87930 (19)0.03398 (7)0.35662 (10)0.0245 (3)
H210.95000.02800.31560.029*
C220.80949 (18)0.09223 (7)0.36718 (9)0.0202 (3)
H220.83160.12570.33310.024*
C230.57756 (17)0.20051 (6)0.37482 (8)0.0158 (3)
H230.59890.18650.32310.019*
C240.50103 (17)0.25886 (6)0.37916 (8)0.0140 (2)
C250.45972 (16)0.29810 (6)0.30672 (8)0.0145 (2)
C260.36654 (18)0.35218 (6)0.31416 (9)0.0187 (3)
H260.33620.36370.36530.022*
C270.31824 (19)0.38901 (7)0.24702 (9)0.0221 (3)
H270.25540.42580.25230.027*
C280.36168 (19)0.37208 (7)0.17210 (9)0.0222 (3)
H280.32640.39690.12600.027*
C290.45660 (19)0.31897 (7)0.16435 (9)0.0211 (3)
H290.48740.30780.11310.025*
C300.50646 (17)0.28211 (7)0.23134 (8)0.0171 (3)
H300.57230.24600.22600.020*
C310.3563 (8)0.4768 (3)0.4741 (4)0.0210 (10)0.50
C320.4464 (8)0.4664 (3)0.5497 (4)0.0265 (13)0.50
H320.40190.43980.58720.032*0.50
C330.6015 (8)0.4950 (3)0.5706 (4)0.0285 (14)0.50
H330.66310.48790.62230.034*0.50
C340.6666 (8)0.5339 (3)0.5158 (5)0.0315 (15)0.50
H340.77260.55350.53000.038*0.50
C350.5765 (9)0.5443 (4)0.4401 (5)0.0266 (12)0.50
H350.62100.57090.40270.032*0.50
C360.4214 (9)0.5158 (3)0.4193 (4)0.0260 (12)0.50
H360.35990.52290.36760.031*0.50
C370.1816 (4)0.44999 (16)0.4561 (2)0.0292 (7)0.50
H37A0.18310.40640.47300.044*0.50
H37B0.14410.45270.39800.044*0.50
H37C0.10410.47340.48570.044*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01623 (5)0.01190 (5)0.00992 (5)0.00085 (3)0.00233 (3)0.00018 (3)
Cl10.02183 (16)0.01610 (15)0.01564 (15)0.00272 (11)0.00060 (12)0.00137 (11)
Cl20.01985 (15)0.01574 (15)0.01997 (16)0.00295 (11)0.00608 (12)0.00062 (12)
O10.0185 (5)0.0165 (5)0.0126 (4)0.0016 (4)0.0038 (4)0.0010 (4)
O20.0221 (5)0.0148 (4)0.0119 (4)0.0004 (4)0.0012 (4)0.0007 (3)
O30.0206 (5)0.0164 (5)0.0128 (4)0.0043 (4)0.0021 (4)0.0008 (4)
O40.0231 (5)0.0134 (4)0.0122 (4)0.0012 (4)0.0048 (4)0.0003 (3)
C10.0153 (6)0.0138 (6)0.0143 (6)0.0014 (5)0.0007 (5)0.0015 (5)
C20.0188 (6)0.0195 (7)0.0181 (7)0.0000 (5)0.0040 (5)0.0013 (5)
C30.0184 (7)0.0219 (7)0.0260 (8)0.0028 (5)0.0060 (6)0.0015 (6)
C40.0186 (7)0.0165 (6)0.0264 (7)0.0016 (5)0.0020 (6)0.0007 (5)
C50.0249 (7)0.0169 (6)0.0174 (7)0.0007 (5)0.0005 (5)0.0023 (5)
C60.0199 (6)0.0171 (6)0.0160 (6)0.0005 (5)0.0032 (5)0.0010 (5)
C70.0140 (6)0.0141 (6)0.0144 (6)0.0028 (5)0.0013 (5)0.0007 (5)
C80.0183 (6)0.0169 (7)0.0126 (6)0.0000 (5)0.0015 (5)0.0005 (5)
C90.0148 (6)0.0145 (6)0.0135 (6)0.0032 (5)0.0021 (5)0.0012 (5)
C100.0150 (6)0.0165 (6)0.0143 (6)0.0016 (5)0.0012 (5)0.0032 (5)
C110.0232 (7)0.0230 (7)0.0161 (7)0.0050 (5)0.0017 (5)0.0014 (5)
C120.0297 (8)0.0335 (8)0.0140 (7)0.0048 (6)0.0035 (6)0.0032 (6)
C130.0277 (8)0.0292 (8)0.0217 (7)0.0021 (6)0.0071 (6)0.0106 (6)
C140.0239 (7)0.0186 (7)0.0271 (8)0.0015 (5)0.0060 (6)0.0057 (6)
C150.0207 (7)0.0156 (6)0.0191 (7)0.0020 (5)0.0040 (5)0.0011 (5)
C160.0137 (6)0.0141 (6)0.0162 (6)0.0021 (5)0.0027 (5)0.0021 (5)
C170.0142 (6)0.0140 (6)0.0171 (6)0.0004 (5)0.0008 (5)0.0029 (5)
C180.0196 (6)0.0168 (6)0.0178 (7)0.0010 (5)0.0006 (5)0.0017 (5)
C190.0254 (7)0.0153 (6)0.0254 (7)0.0014 (5)0.0018 (6)0.0002 (5)
C200.0206 (7)0.0178 (7)0.0330 (8)0.0049 (5)0.0025 (6)0.0080 (6)
C210.0189 (7)0.0249 (7)0.0304 (8)0.0029 (6)0.0063 (6)0.0080 (6)
C220.0186 (7)0.0190 (7)0.0236 (7)0.0003 (5)0.0049 (5)0.0028 (5)
C230.0196 (6)0.0151 (6)0.0133 (6)0.0001 (5)0.0048 (5)0.0017 (5)
C240.0151 (6)0.0138 (6)0.0132 (6)0.0026 (5)0.0025 (5)0.0006 (5)
C250.0155 (6)0.0144 (6)0.0138 (6)0.0032 (5)0.0023 (5)0.0002 (5)
C260.0218 (7)0.0178 (7)0.0168 (6)0.0003 (5)0.0036 (5)0.0009 (5)
C270.0229 (7)0.0185 (7)0.0245 (7)0.0020 (5)0.0015 (6)0.0044 (6)
C280.0217 (7)0.0248 (7)0.0188 (7)0.0041 (6)0.0023 (5)0.0081 (6)
C290.0231 (7)0.0268 (7)0.0134 (6)0.0057 (6)0.0025 (5)0.0018 (5)
C300.0180 (6)0.0184 (6)0.0150 (6)0.0029 (5)0.0029 (5)0.0001 (5)
C310.023 (2)0.018 (2)0.024 (2)0.0032 (17)0.0075 (19)0.0015 (16)
C320.041 (3)0.017 (3)0.025 (2)0.006 (2)0.017 (2)0.0064 (19)
C330.034 (3)0.028 (3)0.021 (2)0.011 (2)0.003 (2)0.004 (2)
C340.030 (2)0.026 (3)0.042 (3)0.0038 (19)0.016 (2)0.010 (2)
C350.033 (2)0.017 (2)0.032 (3)0.0018 (16)0.012 (2)0.0031 (19)
C360.034 (2)0.019 (2)0.028 (2)0.0038 (18)0.0139 (19)0.0056 (17)
C370.0278 (16)0.0270 (16)0.0324 (17)0.0008 (12)0.0020 (13)0.0004 (13)
Geometric parameters (Å, º) top
Sn1—O42.0477 (9)C17—C181.3981 (19)
Sn1—O22.0515 (10)C18—C191.391 (2)
Sn1—O32.0646 (9)C18—H180.9500
Sn1—O12.0756 (10)C19—C201.386 (2)
Sn1—Cl22.3667 (3)C19—H190.9500
Sn1—Cl12.3840 (3)C20—C211.385 (2)
O1—C71.2904 (16)C20—H200.9500
O2—C91.2981 (16)C21—C221.395 (2)
O3—C161.2962 (16)C21—H210.9500
O4—C241.2957 (16)C22—H220.9500
C1—C61.3961 (19)C23—C241.4049 (18)
C1—C21.3959 (19)C23—H230.9500
C1—C71.4906 (18)C24—C251.4779 (18)
C2—C31.390 (2)C25—C261.3978 (19)
C2—H20.9500C25—C301.3997 (19)
C3—C41.389 (2)C26—C271.387 (2)
C3—H30.9500C26—H260.9500
C4—C51.389 (2)C27—C281.388 (2)
C4—H40.9500C27—H270.9500
C5—C61.390 (2)C28—C291.389 (2)
C5—H50.9500C28—H280.9500
C6—H60.9500C29—C301.388 (2)
C7—C81.3963 (19)C29—H290.9500
C8—C91.3984 (19)C30—H300.9500
C8—H80.9500C31—C321.3900
C9—C101.4826 (18)C31—C361.3900
C10—C111.399 (2)C31—C371.507 (6)
C10—C151.4005 (19)C32—C331.3900
C11—C121.388 (2)C32—H320.9500
C11—H110.9500C33—C341.3900
C12—C131.389 (2)C33—H330.9500
C12—H120.9500C34—C351.3900
C13—C141.393 (2)C34—H340.9500
C13—H130.9500C35—C361.3900
C14—C151.386 (2)C35—H350.9500
C14—H140.9500C36—H360.9500
C15—H150.9500C37—H37A0.9800
C16—C231.3893 (19)C37—H37B0.9800
C16—C171.4870 (18)C37—H37C0.9800
C17—C221.3962 (19)
O4—Sn1—O2169.82 (4)O3—C16—C23125.49 (12)
O4—Sn1—O386.03 (4)O3—C16—C17114.46 (12)
O2—Sn1—O387.00 (4)C23—C16—C17120.02 (12)
O4—Sn1—O186.12 (4)C22—C17—C18119.43 (13)
O2—Sn1—O186.20 (4)C22—C17—C16122.25 (12)
O3—Sn1—O187.74 (4)C18—C17—C16118.30 (12)
O4—Sn1—Cl292.91 (3)C19—C18—C17120.31 (13)
O2—Sn1—Cl293.72 (3)C19—C18—H18119.8
O3—Sn1—Cl2177.21 (3)C17—C18—H18119.8
O1—Sn1—Cl289.61 (3)C20—C19—C18119.86 (14)
O4—Sn1—Cl194.56 (3)C20—C19—H19120.1
O2—Sn1—Cl192.76 (3)C18—C19—H19120.1
O3—Sn1—Cl189.29 (3)C19—C20—C21120.31 (14)
O1—Sn1—Cl1176.90 (3)C19—C20—H20119.8
Cl2—Sn1—Cl193.366 (12)C21—C20—H20119.8
C7—O1—Sn1123.02 (8)C20—C21—C22120.20 (14)
C9—O2—Sn1124.27 (8)C20—C21—H21119.9
C16—O3—Sn1124.44 (8)C22—C21—H21119.9
C24—O4—Sn1126.03 (8)C17—C22—C21119.88 (14)
C6—C1—C2119.22 (13)C17—C22—H22120.1
C6—C1—C7121.41 (12)C21—C22—H22120.1
C2—C1—C7119.37 (12)C16—C23—C24125.10 (12)
C3—C2—C1120.31 (13)C16—C23—H23117.4
C3—C2—H2119.8C24—C23—H23117.4
C1—C2—H2119.8O4—C24—C23123.80 (12)
C4—C3—C2120.20 (13)O4—C24—C25114.60 (11)
C4—C3—H3119.9C23—C24—C25121.60 (12)
C2—C3—H3119.9C26—C25—C30119.42 (13)
C5—C4—C3119.78 (13)C26—C25—C24118.11 (12)
C5—C4—H4120.1C30—C25—C24122.44 (12)
C3—C4—H4120.1C27—C26—C25120.19 (13)
C4—C5—C6120.20 (13)C27—C26—H26119.9
C4—C5—H5119.9C25—C26—H26119.9
C6—C5—H5119.9C28—C27—C26120.04 (14)
C5—C6—C1120.27 (13)C28—C27—H27120.0
C5—C6—H6119.9C26—C27—H27120.0
C1—C6—H6119.9C27—C28—C29120.19 (13)
O1—C7—C8125.22 (12)C27—C28—H28119.9
O1—C7—C1115.09 (12)C29—C28—H28119.9
C8—C7—C1119.67 (12)C30—C29—C28120.11 (14)
C7—C8—C9125.32 (13)C30—C29—H29119.9
C7—C8—H8117.3C28—C29—H29119.9
C9—C8—H8117.3C29—C30—C25120.02 (13)
O2—C9—C8124.37 (12)C29—C30—H30120.0
O2—C9—C10114.66 (12)C25—C30—H30120.0
C8—C9—C10120.97 (12)C32—C31—C36120.0
C11—C10—C15119.09 (13)C32—C31—C37118.7 (3)
C11—C10—C9121.86 (12)C36—C31—C37121.1 (3)
C15—C10—C9118.96 (12)C33—C32—C31120.0
C12—C11—C10120.17 (14)C33—C32—H32120.0
C12—C11—H11119.9C31—C32—H32120.0
C10—C11—H11119.9C32—C33—C34120.0
C13—C12—C11120.38 (15)C32—C33—H33120.0
C13—C12—H12119.8C34—C33—H33120.0
C11—C12—H12119.8C35—C34—C33120.0
C12—C13—C14119.80 (14)C35—C34—H34120.0
C12—C13—H13120.1C33—C34—H34120.0
C14—C13—H13120.1C36—C35—C34120.0
C15—C14—C13120.07 (14)C36—C35—H35120.0
C15—C14—H14120.0C34—C35—H35120.0
C13—C14—H14120.0C35—C36—C31120.0
C14—C15—C10120.46 (14)C35—C36—H36120.0
C14—C15—H15119.8C31—C36—H36120.0
C10—C15—H15119.8
O4—Sn1—O1—C7153.37 (10)C11—C12—C13—C140.2 (2)
O2—Sn1—O1—C733.32 (10)C12—C13—C14—C151.2 (2)
O3—Sn1—O1—C7120.46 (10)C13—C14—C15—C101.1 (2)
Cl2—Sn1—O1—C760.43 (10)C11—C10—C15—C140.3 (2)
O4—Sn1—O2—C974.0 (2)C9—C10—C15—C14176.28 (13)
O3—Sn1—O2—C9120.85 (10)Sn1—O3—C16—C2319.78 (18)
O1—Sn1—O2—C932.92 (10)Sn1—O3—C16—C17158.46 (9)
Cl2—Sn1—O2—C956.45 (10)O3—C16—C17—C22150.91 (13)
Cl1—Sn1—O2—C9150.00 (10)C23—C16—C17—C2230.7 (2)
O4—Sn1—O3—C1629.25 (10)O3—C16—C17—C1830.91 (17)
O2—Sn1—O3—C16158.17 (11)C23—C16—C17—C18147.44 (13)
O1—Sn1—O3—C16115.51 (10)C22—C17—C18—C191.2 (2)
Cl1—Sn1—O3—C1665.37 (10)C16—C17—C18—C19177.04 (13)
O2—Sn1—O4—C2476.8 (2)C17—C18—C19—C201.1 (2)
O3—Sn1—O4—C2429.95 (11)C18—C19—C20—C210.1 (2)
O1—Sn1—O4—C24117.95 (11)C19—C20—C21—C220.8 (2)
Cl2—Sn1—O4—C24152.63 (11)C18—C17—C22—C210.3 (2)
Cl1—Sn1—O4—C2459.02 (11)C16—C17—C22—C21177.86 (13)
C6—C1—C2—C30.5 (2)C20—C21—C22—C170.7 (2)
C7—C1—C2—C3179.98 (13)O3—C16—C23—C242.7 (2)
C1—C2—C3—C41.3 (2)C17—C16—C23—C24179.11 (13)
C2—C3—C4—C50.7 (2)Sn1—O4—C24—C2320.39 (19)
C3—C4—C5—C60.7 (2)Sn1—O4—C24—C25158.82 (9)
C4—C5—C6—C11.6 (2)C16—C23—C24—O42.7 (2)
C2—C1—C6—C51.0 (2)C16—C23—C24—C25178.13 (12)
C7—C1—C6—C5178.56 (13)O4—C24—C25—C266.43 (18)
Sn1—O1—C7—C822.71 (18)C23—C24—C25—C26172.79 (13)
Sn1—O1—C7—C1158.92 (8)O4—C24—C25—C30175.33 (12)
C6—C1—C7—O1153.74 (12)C23—C24—C25—C305.4 (2)
C2—C1—C7—O125.77 (18)C30—C25—C26—C271.2 (2)
C6—C1—C7—C827.79 (19)C24—C25—C26—C27177.09 (13)
C2—C1—C7—C8152.70 (13)C25—C26—C27—C280.3 (2)
O1—C7—C8—C93.1 (2)C26—C27—C28—C291.4 (2)
C1—C7—C8—C9175.23 (13)C27—C28—C29—C300.9 (2)
Sn1—O2—C9—C821.43 (18)C28—C29—C30—C250.6 (2)
Sn1—O2—C9—C10158.76 (9)C26—C25—C30—C291.7 (2)
C7—C8—C9—O24.1 (2)C24—C25—C30—C29176.55 (13)
C7—C8—C9—C10175.70 (13)C36—C31—C32—C330.0
O2—C9—C10—C11169.73 (13)C37—C31—C32—C33174.4 (4)
C8—C9—C10—C1110.4 (2)C31—C32—C33—C340.0
O2—C9—C10—C156.79 (18)C32—C33—C34—C350.0
C8—C9—C10—C15173.03 (13)C33—C34—C35—C360.0
C15—C10—C11—C121.8 (2)C34—C35—C36—C310.0
C9—C10—C11—C12174.76 (14)C32—C31—C36—C350.0
C10—C11—C12—C131.7 (2)C37—C31—C36—C35174.2 (4)

Experimental details

Crystal data
Chemical formula[Sn(C15H11O2)2Cl2]·0.5C7H8
Mr682.13
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)8.0024 (1), 21.5554 (2), 16.6838 (2)
β (°) 97.2740 (5)
V3)2854.71 (6)
Z4
Radiation typeMo Kα
µ (mm1)1.12
Crystal size (mm)0.40 × 0.35 × 0.30
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.663, 0.730
No. of measured, independent and
observed [I > 2σ(I)] reflections
23143, 6534, 6269
Rint0.014
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.018, 0.049, 1.02
No. of reflections6534
No. of parameters386
No. of restraints43
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.51, 0.48

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

Acknowledgements

We thank the University of Malaya (RG020/09AFR) for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSearle, D., Smith, P. J., Bell, N. A., March, L. A., Nowell, I. W. & Donaldson, J. D. (1989). Inorg. Chim. Acta, 162, 143–149.  CSD CrossRef CAS Web of Science Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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