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

Thy, C.K.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536810028084

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m992

https://doi.org/10.1107/S1600536810028084

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

Chun Keng Thy,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^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 ).

Experimental

Crystal data

[Sn(C₁₅H₁₁O₂)₂Cl₂]·0.5C₇H₈
M_r = 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 ) T_min = 0.663, T_max = 0.730
23143 measured reflections
6534 independent reflections
6269 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810028084/bt5299sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810028084/bt5299Isup2.hkl

checkCIF report

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–carbon_benzyl 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.

Structure description top

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

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]·0.5C₇H₈	F(000) = 1372
M_r = 682.13	D_x = 1.587 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9775 reflections
a = 8.0024 (1) Å	θ = 2.6–28.3°
b = 21.5554 (2) Å	µ = 1.12 mm⁻¹
c = 16.6838 (2) Å	T = 100 K
β = 97.2740 (5)°	Block, colorless
V = 2854.71 (6) Å³	0.40 × 0.35 × 0.30 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	6534 independent reflections
Radiation source: fine-focus sealed tube	6269 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.663, T_max = 0.730	k = −28→27
23143 measured reflections	l = −21→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.049	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0264P)² + 1.8695P] where P = (F_o² + 2F_c²)/3
6534 reflections	(Δ/σ)_max = 0.001
386 parameters	Δρ_max = 0.51 e Å⁻³
43 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Sn(C₁₅H₁₁O₂)₂Cl₂]·0.5C₇H₈	V = 2854.71 (6) Å³
M_r = 682.13	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0024 (1) Å	µ = 1.12 mm⁻¹
b = 21.5554 (2) Å	T = 100 K
c = 16.6838 (2) Å	0.40 × 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)
T_min = 0.663, T_max = 0.730	R_int = 0.014
23143 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	43 restraints
wR(F²) = 0.049	H-atom parameters constrained
S = 1.02	Δρ_max = 0.51 e Å⁻³
6534 reflections	Δρ_min = −0.48 e Å⁻³
386 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.423028 (11)	0.234239 (4)	0.547401 (5)	0.01263 (4)
Cl1	0.20470 (4)	0.170342 (15)	0.48111 (2)	0.01801 (7)
Cl2	0.23181 (4)	0.308712 (15)	0.58666 (2)	0.01822 (7)
O1	0.62198 (12)	0.28585 (4)	0.60498 (6)	0.01569 (18)
O2	0.43258 (12)	0.18534 (4)	0.65338 (6)	0.01634 (19)
O3	0.59905 (12)	0.17245 (4)	0.51420 (6)	0.01660 (19)
O4	0.45921 (13)	0.28244 (4)	0.44524 (6)	0.01604 (19)
C1	0.74806 (17)	0.35237 (6)	0.70667 (8)	0.0146 (2)
C2	0.87260 (18)	0.37017 (7)	0.65982 (9)	0.0187 (3)
H2	0.8871	0.3476	0.6123	0.022*
C3	0.97545 (18)	0.42080 (7)	0.68234 (9)	0.0219 (3)
H3	1.0615	0.4321	0.6508	0.026*
C4	0.95274 (18)	0.45488 (7)	0.75081 (9)	0.0209 (3)
H4	1.0223	0.4898	0.7658	0.025*
C5	0.82797 (19)	0.43778 (7)	0.79729 (9)	0.0199 (3)
H5	0.8114	0.4613	0.8438	0.024*
C6	0.72730 (18)	0.38632 (6)	0.77598 (8)	0.0176 (3)
H6	0.6440	0.3742	0.8087	0.021*
C7	0.63927 (16)	0.29790 (6)	0.68135 (8)	0.0142 (2)
C8	0.56859 (18)	0.26349 (6)	0.73948 (8)	0.0160 (3)
H8	0.5858	0.2782	0.7936	0.019*
C9	0.47456 (16)	0.20909 (6)	0.72458 (8)	0.0142 (2)
C10	0.41507 (17)	0.17367 (6)	0.79168 (8)	0.0153 (2)
C11	0.42603 (19)	0.19764 (7)	0.87008 (9)	0.0208 (3)
H11	0.4811	0.2361	0.8825	0.025*
C12	0.3567 (2)	0.16530 (8)	0.92983 (9)	0.0257 (3)
H12	0.3618	0.1823	0.9826	0.031*
C13	0.2798 (2)	0.10820 (8)	0.91288 (10)	0.0259 (3)
H13	0.2328	0.0862	0.9540	0.031*
C14	0.27184 (19)	0.08334 (7)	0.83542 (10)	0.0230 (3)
H14	0.2213	0.0439	0.8239	0.028*
C15	0.33758 (18)	0.11603 (6)	0.77509 (9)	0.0183 (3)
H15	0.3300	0.0992	0.7221	0.022*
C16	0.62450 (16)	0.16168 (6)	0.44027 (8)	0.0146 (2)
C17	0.70704 (16)	0.10122 (6)	0.42799 (8)	0.0153 (3)
C18	0.67625 (18)	0.05155 (6)	0.47798 (9)	0.0182 (3)
H18	0.6084	0.0576	0.5201	0.022*
C19	0.74452 (19)	−0.00663 (7)	0.46630 (9)	0.0225 (3)
H19	0.7217	−0.0404	0.4998	0.027*
C20	0.84583 (19)	−0.01515 (7)	0.40570 (10)	0.0243 (3)
H20	0.8925	−0.0549	0.3978	0.029*
C21	0.87930 (19)	0.03398 (7)	0.35662 (10)	0.0245 (3)
H21	0.9500	0.0280	0.3156	0.029*
C22	0.80949 (18)	0.09223 (7)	0.36718 (9)	0.0202 (3)
H22	0.8316	0.1257	0.3331	0.024*
C23	0.57756 (17)	0.20051 (6)	0.37482 (8)	0.0158 (3)
H23	0.5989	0.1865	0.3231	0.019*
C24	0.50103 (17)	0.25886 (6)	0.37916 (8)	0.0140 (2)
C25	0.45972 (16)	0.29810 (6)	0.30672 (8)	0.0145 (2)
C26	0.36654 (18)	0.35218 (6)	0.31416 (9)	0.0187 (3)
H26	0.3362	0.3637	0.3653	0.022*
C27	0.31824 (19)	0.38901 (7)	0.24702 (9)	0.0221 (3)
H27	0.2554	0.4258	0.2523	0.027*
C28	0.36168 (19)	0.37208 (7)	0.17210 (9)	0.0222 (3)
H28	0.3264	0.3969	0.1260	0.027*
C29	0.45660 (19)	0.31897 (7)	0.16435 (9)	0.0211 (3)
H29	0.4874	0.3078	0.1131	0.025*
C30	0.50646 (17)	0.28211 (7)	0.23134 (8)	0.0171 (3)
H30	0.5723	0.2460	0.2260	0.020*
C31	0.3563 (8)	0.4768 (3)	0.4741 (4)	0.0210 (10)	0.50
C32	0.4464 (8)	0.4664 (3)	0.5497 (4)	0.0265 (13)	0.50
H32	0.4019	0.4398	0.5872	0.032*	0.50
C33	0.6015 (8)	0.4950 (3)	0.5706 (4)	0.0285 (14)	0.50
H33	0.6631	0.4879	0.6223	0.034*	0.50
C34	0.6666 (8)	0.5339 (3)	0.5158 (5)	0.0315 (15)	0.50
H34	0.7726	0.5535	0.5300	0.038*	0.50
C35	0.5765 (9)	0.5443 (4)	0.4401 (5)	0.0266 (12)	0.50
H35	0.6210	0.5709	0.4027	0.032*	0.50
C36	0.4214 (9)	0.5158 (3)	0.4193 (4)	0.0260 (12)	0.50
H36	0.3599	0.5229	0.3676	0.031*	0.50
C37	0.1816 (4)	0.44999 (16)	0.4561 (2)	0.0292 (7)	0.50
H37A	0.1831	0.4064	0.4730	0.044*	0.50
H37B	0.1441	0.4527	0.3980	0.044*	0.50
H37C	0.1041	0.4734	0.4857	0.044*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01623 (5)	0.01190 (5)	0.00992 (5)	0.00085 (3)	0.00233 (3)	−0.00018 (3)
Cl1	0.02183 (16)	0.01610 (15)	0.01564 (15)	−0.00272 (11)	0.00060 (12)	−0.00137 (11)
Cl2	0.01985 (15)	0.01574 (15)	0.01997 (16)	0.00295 (11)	0.00608 (12)	−0.00062 (12)
O1	0.0185 (5)	0.0165 (5)	0.0126 (4)	−0.0016 (4)	0.0038 (4)	−0.0010 (4)
O2	0.0221 (5)	0.0148 (4)	0.0119 (4)	−0.0004 (4)	0.0012 (4)	−0.0007 (3)
O3	0.0206 (5)	0.0164 (5)	0.0128 (4)	0.0043 (4)	0.0021 (4)	−0.0008 (4)
O4	0.0231 (5)	0.0134 (4)	0.0122 (4)	0.0012 (4)	0.0048 (4)	0.0003 (3)
C1	0.0153 (6)	0.0138 (6)	0.0143 (6)	0.0014 (5)	0.0007 (5)	0.0015 (5)
C2	0.0188 (6)	0.0195 (7)	0.0181 (7)	0.0000 (5)	0.0040 (5)	−0.0013 (5)
C3	0.0184 (7)	0.0219 (7)	0.0260 (8)	−0.0028 (5)	0.0060 (6)	0.0015 (6)
C4	0.0186 (7)	0.0165 (6)	0.0264 (7)	−0.0016 (5)	−0.0020 (6)	0.0007 (5)
C5	0.0249 (7)	0.0169 (6)	0.0174 (7)	0.0007 (5)	0.0005 (5)	−0.0023 (5)
C6	0.0199 (6)	0.0171 (6)	0.0160 (6)	0.0005 (5)	0.0032 (5)	0.0010 (5)
C7	0.0140 (6)	0.0141 (6)	0.0144 (6)	0.0028 (5)	0.0013 (5)	−0.0007 (5)
C8	0.0183 (6)	0.0169 (7)	0.0126 (6)	0.0000 (5)	0.0015 (5)	−0.0005 (5)
C9	0.0148 (6)	0.0145 (6)	0.0135 (6)	0.0032 (5)	0.0021 (5)	0.0012 (5)
C10	0.0150 (6)	0.0165 (6)	0.0143 (6)	0.0016 (5)	0.0012 (5)	0.0032 (5)
C11	0.0232 (7)	0.0230 (7)	0.0161 (7)	−0.0050 (5)	0.0017 (5)	0.0014 (5)
C12	0.0297 (8)	0.0335 (8)	0.0140 (7)	−0.0048 (6)	0.0035 (6)	0.0032 (6)
C13	0.0277 (8)	0.0292 (8)	0.0217 (7)	−0.0021 (6)	0.0071 (6)	0.0106 (6)
C14	0.0239 (7)	0.0186 (7)	0.0271 (8)	−0.0015 (5)	0.0060 (6)	0.0057 (6)
C15	0.0207 (7)	0.0156 (6)	0.0191 (7)	0.0020 (5)	0.0040 (5)	0.0011 (5)
C16	0.0137 (6)	0.0141 (6)	0.0162 (6)	−0.0021 (5)	0.0027 (5)	−0.0021 (5)
C17	0.0142 (6)	0.0140 (6)	0.0171 (6)	0.0004 (5)	−0.0008 (5)	−0.0029 (5)
C18	0.0196 (6)	0.0168 (6)	0.0178 (7)	0.0010 (5)	0.0006 (5)	−0.0017 (5)
C19	0.0254 (7)	0.0153 (6)	0.0254 (7)	0.0014 (5)	−0.0018 (6)	−0.0002 (5)
C20	0.0206 (7)	0.0178 (7)	0.0330 (8)	0.0049 (5)	−0.0025 (6)	−0.0080 (6)
C21	0.0189 (7)	0.0249 (7)	0.0304 (8)	0.0029 (6)	0.0063 (6)	−0.0080 (6)
C22	0.0186 (7)	0.0190 (7)	0.0236 (7)	−0.0003 (5)	0.0049 (5)	−0.0028 (5)
C23	0.0196 (6)	0.0151 (6)	0.0133 (6)	−0.0001 (5)	0.0048 (5)	−0.0017 (5)
C24	0.0151 (6)	0.0138 (6)	0.0132 (6)	−0.0026 (5)	0.0025 (5)	−0.0006 (5)
C25	0.0155 (6)	0.0144 (6)	0.0138 (6)	−0.0032 (5)	0.0023 (5)	0.0002 (5)
C26	0.0218 (7)	0.0178 (7)	0.0168 (6)	0.0003 (5)	0.0036 (5)	0.0009 (5)
C27	0.0229 (7)	0.0185 (7)	0.0245 (7)	0.0020 (5)	0.0015 (6)	0.0044 (6)
C28	0.0217 (7)	0.0248 (7)	0.0188 (7)	−0.0041 (6)	−0.0023 (5)	0.0081 (6)
C29	0.0231 (7)	0.0268 (7)	0.0134 (6)	−0.0057 (6)	0.0025 (5)	0.0018 (5)
C30	0.0180 (6)	0.0184 (6)	0.0150 (6)	−0.0029 (5)	0.0029 (5)	−0.0001 (5)
C31	0.023 (2)	0.018 (2)	0.024 (2)	0.0032 (17)	0.0075 (19)	0.0015 (16)
C32	0.041 (3)	0.017 (3)	0.025 (2)	0.006 (2)	0.017 (2)	0.0064 (19)
C33	0.034 (3)	0.028 (3)	0.021 (2)	0.011 (2)	−0.003 (2)	−0.004 (2)
C34	0.030 (2)	0.026 (3)	0.042 (3)	−0.0038 (19)	0.016 (2)	−0.010 (2)
C35	0.033 (2)	0.017 (2)	0.032 (3)	−0.0018 (16)	0.012 (2)	0.0031 (19)
C36	0.034 (2)	0.019 (2)	0.028 (2)	0.0038 (18)	0.0139 (19)	0.0056 (17)
C37	0.0278 (16)	0.0270 (16)	0.0324 (17)	−0.0008 (12)	0.0020 (13)	−0.0004 (13)

Geometric parameters (Å, º) top

Sn1—O4	2.0477 (9)	C17—C18	1.3981 (19)
Sn1—O2	2.0515 (10)	C18—C19	1.391 (2)
Sn1—O3	2.0646 (9)	C18—H18	0.9500
Sn1—O1	2.0756 (10)	C19—C20	1.386 (2)
Sn1—Cl2	2.3667 (3)	C19—H19	0.9500
Sn1—Cl1	2.3840 (3)	C20—C21	1.385 (2)
O1—C7	1.2904 (16)	C20—H20	0.9500
O2—C9	1.2981 (16)	C21—C22	1.395 (2)
O3—C16	1.2962 (16)	C21—H21	0.9500
O4—C24	1.2957 (16)	C22—H22	0.9500
C1—C6	1.3961 (19)	C23—C24	1.4049 (18)
C1—C2	1.3959 (19)	C23—H23	0.9500
C1—C7	1.4906 (18)	C24—C25	1.4779 (18)
C2—C3	1.390 (2)	C25—C26	1.3978 (19)
C2—H2	0.9500	C25—C30	1.3997 (19)
C3—C4	1.389 (2)	C26—C27	1.387 (2)
C3—H3	0.9500	C26—H26	0.9500
C4—C5	1.389 (2)	C27—C28	1.388 (2)
C4—H4	0.9500	C27—H27	0.9500
C5—C6	1.390 (2)	C28—C29	1.389 (2)
C5—H5	0.9500	C28—H28	0.9500
C6—H6	0.9500	C29—C30	1.388 (2)
C7—C8	1.3963 (19)	C29—H29	0.9500
C8—C9	1.3984 (19)	C30—H30	0.9500
C8—H8	0.9500	C31—C32	1.3900
C9—C10	1.4826 (18)	C31—C36	1.3900
C10—C11	1.399 (2)	C31—C37	1.507 (6)
C10—C15	1.4005 (19)	C32—C33	1.3900
C11—C12	1.388 (2)	C32—H32	0.9500
C11—H11	0.9500	C33—C34	1.3900
C12—C13	1.389 (2)	C33—H33	0.9500
C12—H12	0.9500	C34—C35	1.3900
C13—C14	1.393 (2)	C34—H34	0.9500
C13—H13	0.9500	C35—C36	1.3900
C14—C15	1.386 (2)	C35—H35	0.9500
C14—H14	0.9500	C36—H36	0.9500
C15—H15	0.9500	C37—H37A	0.9800
C16—C23	1.3893 (19)	C37—H37B	0.9800
C16—C17	1.4870 (18)	C37—H37C	0.9800
C17—C22	1.3962 (19)

O4—Sn1—O2	169.82 (4)	O3—C16—C23	125.49 (12)
O4—Sn1—O3	86.03 (4)	O3—C16—C17	114.46 (12)
O2—Sn1—O3	87.00 (4)	C23—C16—C17	120.02 (12)
O4—Sn1—O1	86.12 (4)	C22—C17—C18	119.43 (13)
O2—Sn1—O1	86.20 (4)	C22—C17—C16	122.25 (12)
O3—Sn1—O1	87.74 (4)	C18—C17—C16	118.30 (12)
O4—Sn1—Cl2	92.91 (3)	C19—C18—C17	120.31 (13)
O2—Sn1—Cl2	93.72 (3)	C19—C18—H18	119.8
O3—Sn1—Cl2	177.21 (3)	C17—C18—H18	119.8
O1—Sn1—Cl2	89.61 (3)	C20—C19—C18	119.86 (14)
O4—Sn1—Cl1	94.56 (3)	C20—C19—H19	120.1
O2—Sn1—Cl1	92.76 (3)	C18—C19—H19	120.1
O3—Sn1—Cl1	89.29 (3)	C19—C20—C21	120.31 (14)
O1—Sn1—Cl1	176.90 (3)	C19—C20—H20	119.8
Cl2—Sn1—Cl1	93.366 (12)	C21—C20—H20	119.8
C7—O1—Sn1	123.02 (8)	C20—C21—C22	120.20 (14)
C9—O2—Sn1	124.27 (8)	C20—C21—H21	119.9
C16—O3—Sn1	124.44 (8)	C22—C21—H21	119.9
C24—O4—Sn1	126.03 (8)	C17—C22—C21	119.88 (14)
C6—C1—C2	119.22 (13)	C17—C22—H22	120.1
C6—C1—C7	121.41 (12)	C21—C22—H22	120.1
C2—C1—C7	119.37 (12)	C16—C23—C24	125.10 (12)
C3—C2—C1	120.31 (13)	C16—C23—H23	117.4
C3—C2—H2	119.8	C24—C23—H23	117.4
C1—C2—H2	119.8	O4—C24—C23	123.80 (12)
C4—C3—C2	120.20 (13)	O4—C24—C25	114.60 (11)
C4—C3—H3	119.9	C23—C24—C25	121.60 (12)
C2—C3—H3	119.9	C26—C25—C30	119.42 (13)
C5—C4—C3	119.78 (13)	C26—C25—C24	118.11 (12)
C5—C4—H4	120.1	C30—C25—C24	122.44 (12)
C3—C4—H4	120.1	C27—C26—C25	120.19 (13)
C4—C5—C6	120.20 (13)	C27—C26—H26	119.9
C4—C5—H5	119.9	C25—C26—H26	119.9
C6—C5—H5	119.9	C28—C27—C26	120.04 (14)
C5—C6—C1	120.27 (13)	C28—C27—H27	120.0
C5—C6—H6	119.9	C26—C27—H27	120.0
C1—C6—H6	119.9	C27—C28—C29	120.19 (13)
O1—C7—C8	125.22 (12)	C27—C28—H28	119.9
O1—C7—C1	115.09 (12)	C29—C28—H28	119.9
C8—C7—C1	119.67 (12)	C30—C29—C28	120.11 (14)
C7—C8—C9	125.32 (13)	C30—C29—H29	119.9
C7—C8—H8	117.3	C28—C29—H29	119.9
C9—C8—H8	117.3	C29—C30—C25	120.02 (13)
O2—C9—C8	124.37 (12)	C29—C30—H30	120.0
O2—C9—C10	114.66 (12)	C25—C30—H30	120.0
C8—C9—C10	120.97 (12)	C32—C31—C36	120.0
C11—C10—C15	119.09 (13)	C32—C31—C37	118.7 (3)
C11—C10—C9	121.86 (12)	C36—C31—C37	121.1 (3)
C15—C10—C9	118.96 (12)	C33—C32—C31	120.0
C12—C11—C10	120.17 (14)	C33—C32—H32	120.0
C12—C11—H11	119.9	C31—C32—H32	120.0
C10—C11—H11	119.9	C32—C33—C34	120.0
C13—C12—C11	120.38 (15)	C32—C33—H33	120.0
C13—C12—H12	119.8	C34—C33—H33	120.0
C11—C12—H12	119.8	C35—C34—C33	120.0
C12—C13—C14	119.80 (14)	C35—C34—H34	120.0
C12—C13—H13	120.1	C33—C34—H34	120.0
C14—C13—H13	120.1	C36—C35—C34	120.0
C15—C14—C13	120.07 (14)	C36—C35—H35	120.0
C15—C14—H14	120.0	C34—C35—H35	120.0
C13—C14—H14	120.0	C35—C36—C31	120.0
C14—C15—C10	120.46 (14)	C35—C36—H36	120.0
C14—C15—H15	119.8	C31—C36—H36	120.0
C10—C15—H15	119.8

O4—Sn1—O1—C7	153.37 (10)	C11—C12—C13—C14	−0.2 (2)
O2—Sn1—O1—C7	−33.32 (10)	C12—C13—C14—C15	−1.2 (2)
O3—Sn1—O1—C7	−120.46 (10)	C13—C14—C15—C10	1.1 (2)
Cl2—Sn1—O1—C7	60.43 (10)	C11—C10—C15—C14	0.3 (2)
O4—Sn1—O2—C9	74.0 (2)	C9—C10—C15—C14	−176.28 (13)
O3—Sn1—O2—C9	120.85 (10)	Sn1—O3—C16—C23	19.78 (18)
O1—Sn1—O2—C9	32.92 (10)	Sn1—O3—C16—C17	−158.46 (9)
Cl2—Sn1—O2—C9	−56.45 (10)	O3—C16—C17—C22	−150.91 (13)
Cl1—Sn1—O2—C9	−150.00 (10)	C23—C16—C17—C22	30.7 (2)
O4—Sn1—O3—C16	−29.25 (10)	O3—C16—C17—C18	30.91 (17)
O2—Sn1—O3—C16	158.17 (11)	C23—C16—C17—C18	−147.44 (13)
O1—Sn1—O3—C16	−115.51 (10)	C22—C17—C18—C19	−1.2 (2)
Cl1—Sn1—O3—C16	65.37 (10)	C16—C17—C18—C19	177.04 (13)
O2—Sn1—O4—C24	76.8 (2)	C17—C18—C19—C20	1.1 (2)
O3—Sn1—O4—C24	29.95 (11)	C18—C19—C20—C21	−0.1 (2)
O1—Sn1—O4—C24	117.95 (11)	C19—C20—C21—C22	−0.8 (2)
Cl2—Sn1—O4—C24	−152.63 (11)	C18—C17—C22—C21	0.3 (2)
Cl1—Sn1—O4—C24	−59.02 (11)	C16—C17—C22—C21	−177.86 (13)
C6—C1—C2—C3	0.5 (2)	C20—C21—C22—C17	0.7 (2)
C7—C1—C2—C3	−179.98 (13)	O3—C16—C23—C24	2.7 (2)
C1—C2—C3—C4	−1.3 (2)	C17—C16—C23—C24	−179.11 (13)
C2—C3—C4—C5	0.7 (2)	Sn1—O4—C24—C23	−20.39 (19)
C3—C4—C5—C6	0.7 (2)	Sn1—O4—C24—C25	158.82 (9)
C4—C5—C6—C1	−1.6 (2)	C16—C23—C24—O4	−2.7 (2)
C2—C1—C6—C5	1.0 (2)	C16—C23—C24—C25	178.13 (12)
C7—C1—C6—C5	−178.56 (13)	O4—C24—C25—C26	−6.43 (18)
Sn1—O1—C7—C8	22.71 (18)	C23—C24—C25—C26	172.79 (13)
Sn1—O1—C7—C1	−158.92 (8)	O4—C24—C25—C30	175.33 (12)
C6—C1—C7—O1	153.74 (12)	C23—C24—C25—C30	−5.4 (2)
C2—C1—C7—O1	−25.77 (18)	C30—C25—C26—C27	1.2 (2)
C6—C1—C7—C8	−27.79 (19)	C24—C25—C26—C27	−177.09 (13)
C2—C1—C7—C8	152.70 (13)	C25—C26—C27—C28	0.3 (2)
O1—C7—C8—C9	3.1 (2)	C26—C27—C28—C29	−1.4 (2)
C1—C7—C8—C9	−175.23 (13)	C27—C28—C29—C30	0.9 (2)
Sn1—O2—C9—C8	−21.43 (18)	C28—C29—C30—C25	0.6 (2)
Sn1—O2—C9—C10	158.76 (9)	C26—C25—C30—C29	−1.7 (2)
C7—C8—C9—O2	−4.1 (2)	C24—C25—C30—C29	176.55 (13)
C7—C8—C9—C10	175.70 (13)	C36—C31—C32—C33	0.0
O2—C9—C10—C11	−169.73 (13)	C37—C31—C32—C33	−174.4 (4)
C8—C9—C10—C11	10.4 (2)	C31—C32—C33—C34	0.0
O2—C9—C10—C15	6.79 (18)	C32—C33—C34—C35	0.0
C8—C9—C10—C15	−173.03 (13)	C33—C34—C35—C36	0.0
C15—C10—C11—C12	−1.8 (2)	C34—C35—C36—C31	0.0
C9—C10—C11—C12	174.76 (14)	C32—C31—C36—C35	0.0
C10—C11—C12—C13	1.7 (2)	C37—C31—C36—C35	174.2 (4)

Experimental details

Crystal data
Chemical formula	[Sn(C₁₅H₁₁O₂)₂Cl₂]·0.5C₇H₈
M_r	682.13
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	8.0024 (1), 21.5554 (2), 16.6838 (2)
β (°)	97.2740 (5)
V (Å³)	2854.71 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.40 × 0.35 × 0.30

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.663, 0.730
No. of measured, independent and observed [I > 2σ(I)] reflections	23143, 6534, 6269
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.049, 1.02
No. of reflections	6534
No. of parameters	386
No. of restraints	43
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Searle, 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
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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