Tris(o-chloro­benz­yl)[3-(4-meth­oxybenzoyl)­propionato-κO]tin(IV)

Keng, T.C.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536810005921

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page m315

doi:10.1107/S1600536810005921

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Tris(o-chlorobenzyl)[3-(4-methoxybenzoyl)propionato-κO]tin(IV)

Thy Chun Keng,^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 11 February 2010; accepted 13 February 2010; online 20 February 2010)

The tin atom in the title compound, [Sn(C₇H₆Cl)₃(C₁₁H₁₁O₄)], exists in a distorted tetrahedral coordination environment. The carboxylate anion is equally disordered over two positions.

Related literature

Trialkyltin carboxylates are generally carboxylate-bridged polymers; see: Ng & Kumar Das (1991 ). For the direct synthesis of substituted tribenzyltin chlorides, see: Sisido et al. (1961 ).

Experimental

Crystal data

[Sn(C₇H₆Cl)₃(C₁₁H₁₁O₄)]
M_r = 702.59
Triclinic, $[P \overline 1]$
a = 8.4934 (6) Å
b = 9.2077 (7) Å
c = 21.3736 (16) Å
α = 82.592 (1)°
β = 85.654 (1)°
γ = 66.757 (1)°
V = 1522.47 (19) Å³
Z = 2
Mo Kα radiation
μ = 1.14 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.795, T_max = 1.000
14685 measured reflections
6922 independent reflections
5062 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.114
S = 1.03
6922 reflections
348 parameters
116 restraints
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.41 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: 10.1107/S1600536810005921/xu2728sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005921/xu2728Isup2.hkl

checkCIF report

Related literature top

Trialkyltin carboxylates are generally carboxylate-bridged polymers; see: Ng & Kumar Das (1991). For the direct synthesis of substituted tribenzyltin chlorides, see: Sisido et al. (1961).

Experimental top

3-(4-Methoxyl)benzoylpropionic acid (0.1 g, 0.5 mmol) and tri(o-chlorobenzyl)tin hydroxide (0.25 g, 0.5 mmol) were heated in ethanol (100 ml) for 1 h. After filtering of the mixture, colorless crystals were obtained upon slow evaporation of the filtrate.

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. Thermal ellipsoid plot (Barbour, 2001) of Sn(C₇H₆Cl)₃(C₁₁H₁₁O₄) at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder component of the carboxylate anion is shown in the monodentate mode.
	Fig. 2. Thermal ellipsoid plot (Barbour, 2001) of Sn(C₇H₆Cl)₃(C₁₁H₁₁O₄) at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder component of the carboxylate anion is shown in the chelating mode.

Tris(o-chlorobenzyl)[3-(4-methoxybenzoyl)propionato-κO]tin(IV) top

Crystal data top

[Sn(C₇H₆Cl)₃(C₁₁H₁₁O₄)]	Z = 2
M_r = 702.59	F(000) = 708
Triclinic, P1	D_x = 1.533 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4934 (6) Å	Cell parameters from 3994 reflections
b = 9.2077 (7) Å	θ = 2.4–22.1°
c = 21.3736 (16) Å	µ = 1.14 mm⁻¹
α = 82.592 (1)°	T = 293 K
β = 85.654 (1)°	Prism, colorless
γ = 66.757 (1)°	0.30 × 0.20 × 0.10 mm
V = 1522.47 (19) Å³

Data collection top

Bruker SMART APEX diffractometer	6922 independent reflections
Radiation source: fine-focus sealed tube	5062 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 27.5°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.795, T_max = 1.000	k = −11→11
14685 measured reflections	l = −27→27

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0516P)² + 0.397P] where P = (F_o² + 2F_c²)/3
6922 reflections	(Δ/σ)_max = 0.001
348 parameters	Δρ_max = 0.39 e Å⁻³
116 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Sn(C₇H₆Cl)₃(C₁₁H₁₁O₄)]	γ = 66.757 (1)°
M_r = 702.59	V = 1522.47 (19) Å³
Triclinic, P1	Z = 2
a = 8.4934 (6) Å	Mo Kα radiation
b = 9.2077 (7) Å	µ = 1.14 mm⁻¹
c = 21.3736 (16) Å	T = 293 K
α = 82.592 (1)°	0.30 × 0.20 × 0.10 mm
β = 85.654 (1)°

Data collection top

Bruker SMART APEX diffractometer	6922 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5062 reflections with I > 2σ(I)
T_min = 0.795, T_max = 1.000	R_int = 0.027
14685 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	116 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.03	Δρ_max = 0.39 e Å⁻³
6922 reflections	Δρ_min = −0.41 e Å⁻³
348 parameters

Special details top

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

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.43681 (3)	0.57720 (3)	0.210995 (12)	0.05681 (11)
Cl1	0.26514 (16)	0.91485 (13)	0.09610 (6)	0.0829 (3)
Cl2	0.86070 (17)	0.2126 (2)	0.18407 (7)	0.1150 (5)
Cl3	0.2567 (3)	0.26908 (19)	0.23276 (8)	0.1215 (5)
C1	0.1641 (5)	0.7088 (5)	0.19945 (18)	0.0605 (10)
H1A	0.1026	0.6603	0.2294	0.073*
H1B	0.1341	0.8167	0.2093	0.073*
C2	0.1068 (3)	0.7144 (3)	0.13357 (9)	0.0509 (8)
C3	0.0112 (3)	0.6280 (3)	0.12270 (11)	0.0618 (10)
H3	−0.0205	0.5691	0.1562	0.074*
C4	−0.0369 (3)	0.6296 (3)	0.06181 (13)	0.0714 (11)
H4	−0.1008	0.5717	0.0545	0.086*
C5	0.0105 (4)	0.7176 (3)	0.01178 (9)	0.0733 (12)
H5	−0.0216	0.7187	−0.0290	0.088*
C6	0.1061 (3)	0.8041 (3)	0.02265 (10)	0.0659 (10)
H6	0.1378	0.8630	−0.0108	0.079*
C7	0.1542 (3)	0.8025 (3)	0.08354 (11)	0.0549 (9)
C8	0.5728 (5)	0.5071 (5)	0.1235 (2)	0.0676 (11)
H8A	0.5150	0.5857	0.0891	0.081*
H8B	0.6878	0.5044	0.1251	0.081*
C9	0.5835 (3)	0.3466 (3)	0.11058 (13)	0.0559 (9)
C10	0.4632 (3)	0.3387 (3)	0.07197 (13)	0.0745 (12)
H10	0.3806	0.4317	0.0533	0.089*
C11	0.4664 (4)	0.1919 (4)	0.06124 (15)	0.0962 (16)
H11	0.3859	0.1866	0.0354	0.115*
C12	0.5899 (5)	0.0529 (3)	0.08913 (18)	0.1005 (18)
H12	0.5920	−0.0454	0.0820	0.121*
C13	0.7102 (4)	0.0607 (3)	0.12775 (16)	0.0869 (15)
H13	0.7928	−0.0323	0.1464	0.104*
C14	0.7070 (3)	0.2076 (3)	0.13847 (12)	0.0664 (10)
C15	0.4920 (6)	0.3911 (5)	0.2881 (2)	0.0772 (12)
H15A	0.5436	0.2885	0.2718	0.093*
H15B	0.5733	0.3995	0.3155	0.093*
C16	0.3305 (4)	0.4030 (4)	0.32513 (14)	0.0729 (12)
C17	0.2955 (5)	0.4740 (4)	0.38092 (16)	0.0969 (16)
H17	0.3744	0.5073	0.3959	0.116*
C18	0.1425 (6)	0.4953 (5)	0.41438 (15)	0.132 (3)
H18	0.1191	0.5428	0.4517	0.159*
C19	0.0246 (4)	0.4456 (5)	0.3920 (2)	0.136 (3)
H19	−0.0778	0.4598	0.4144	0.164*
C20	0.0596 (4)	0.3746 (5)	0.3362 (2)	0.122 (2)
H20	−0.0193	0.3413	0.3213	0.146*
C21	0.2126 (5)	0.3533 (4)	0.30278 (15)	0.0834 (13)
O1	0.4575 (9)	0.7580 (9)	0.2569 (3)	0.0768 (14)	0.50
O2	0.7217 (9)	0.6062 (9)	0.2436 (3)	0.0887 (15)	0.50
O3	0.588 (4)	0.655 (3)	0.4097 (15)	0.104 (4)	0.50
O4	0.0927 (11)	0.9380 (10)	0.6204 (4)	0.1084 (18)	0.50
C22	0.6118 (11)	0.7264 (9)	0.2664 (3)	0.081 (2)	0.50
C23	0.6705 (14)	0.8200 (15)	0.3018 (6)	0.075 (3)	0.50
H23A	0.7752	0.7495	0.3227	0.090*	0.50
H23B	0.6982	0.8962	0.2722	0.090*	0.50
C24	0.548 (2)	0.9058 (18)	0.3491 (7)	0.071 (2)	0.50
H24A	0.4394	0.9684	0.3292	0.086*	0.50
H24B	0.5890	0.9788	0.3645	0.086*	0.50
C25	0.5198 (18)	0.802 (3)	0.4030 (6)	0.0772 (15)	0.50
C26	0.403 (2)	0.8541 (13)	0.4597 (6)	0.0708 (14)	0.50
C27	0.4017 (15)	0.7283 (9)	0.5032 (5)	0.081 (2)	0.50
H27	0.4724	0.6245	0.4964	0.097*	0.50
C28	0.2951 (11)	0.7578 (7)	0.5567 (4)	0.082 (2)	0.50
H28	0.2945	0.6736	0.5858	0.099*	0.50
C29	0.1895 (9)	0.9130 (8)	0.5668 (3)	0.072 (2)	0.50
C30	0.1905 (12)	1.0387 (7)	0.5234 (4)	0.081 (2)	0.50
H30	0.1198	1.1426	0.5301	0.097*	0.50
C31	0.2971 (18)	1.0093 (11)	0.4698 (5)	0.078 (2)	0.50
H31	0.2978	1.0934	0.4408	0.094*	0.50
C32	−0.022 (3)	1.0886 (15)	0.6320 (10)	0.124 (4)	0.50
H32A	−0.0767	1.0831	0.6727	0.187*	0.50
H32B	−0.1072	1.1294	0.6001	0.187*	0.50
H32C	0.0383	1.1578	0.6311	0.187*	0.50
O1'	0.3878 (8)	0.7681 (8)	0.2923 (3)	0.0768 (14)	0.50
O2'	0.5929 (9)	0.7007 (9)	0.2224 (3)	0.0887 (15)	0.50
O3'	0.611 (4)	0.677 (3)	0.3979 (15)	0.104 (4)	0.50
O4'	0.0474 (11)	1.0989 (9)	0.5980 (4)	0.1084 (18)	0.50
C22'	0.5231 (10)	0.7763 (8)	0.2700 (3)	0.081 (2)	0.50
C23'	0.6080 (14)	0.8686 (15)	0.2958 (6)	0.075 (3)	0.50
H23C	0.6144	0.9514	0.2640	0.090*	0.50
H23D	0.7237	0.7991	0.3079	0.090*	0.50
C24'	0.506 (2)	0.9411 (19)	0.3522 (7)	0.071 (2)	0.50
H24C	0.5528	1.0112	0.3666	0.086*	0.50
H24D	0.3883	1.0038	0.3407	0.086*	0.50
C25'	0.5114 (19)	0.816 (3)	0.4034 (6)	0.0772 (15)	0.50
C26'	0.389 (2)	0.8780 (13)	0.4571 (6)	0.0708 (14)	0.50
C27'	0.3492 (15)	0.7807 (8)	0.5055 (5)	0.081 (2)	0.50
H27'	0.3991	0.6709	0.5055	0.097*	0.50
C28'	0.2352 (11)	0.8477 (8)	0.5540 (3)	0.082 (2)	0.50
H28'	0.2088	0.7827	0.5864	0.099*	0.50
C29'	0.1607 (9)	1.0120 (8)	0.5540 (3)	0.072 (2)	0.50
C30'	0.2002 (12)	1.1092 (8)	0.5055 (4)	0.081 (2)	0.50
H30'	0.1504	1.2191	0.5055	0.097*	0.50
C31'	0.3142 (18)	1.0422 (12)	0.4571 (5)	0.078 (2)	0.50
H31'	0.3406	1.1073	0.4247	0.094*	0.50
C32'	−0.004 (3)	1.017 (2)	0.6466 (9)	0.124 (4)	0.50
H32D	0.0576	1.0085	0.6836	0.187*	0.50
H32E	0.0174	0.9126	0.6359	0.187*	0.50
H32F	−0.1249	1.0719	0.6549	0.187*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.05296 (17)	0.06063 (18)	0.05656 (17)	−0.02085 (13)	0.00286 (11)	−0.01208 (12)
Cl1	0.0876 (8)	0.0649 (6)	0.1080 (9)	−0.0445 (6)	−0.0020 (7)	−0.0017 (6)
Cl2	0.0662 (8)	0.1523 (14)	0.0965 (10)	−0.0022 (8)	−0.0191 (7)	−0.0315 (9)
Cl3	0.1578 (16)	0.1071 (11)	0.1053 (11)	−0.0565 (11)	−0.0304 (10)	0.0005 (9)
C1	0.057 (2)	0.058 (2)	0.059 (2)	−0.0125 (18)	0.0048 (18)	−0.0129 (18)
C2	0.0423 (19)	0.0439 (18)	0.059 (2)	−0.0094 (15)	0.0026 (16)	−0.0052 (16)
C3	0.054 (2)	0.059 (2)	0.071 (3)	−0.0237 (19)	0.0071 (19)	−0.0021 (19)
C4	0.067 (3)	0.076 (3)	0.081 (3)	−0.035 (2)	−0.005 (2)	−0.017 (2)
C5	0.071 (3)	0.078 (3)	0.061 (3)	−0.016 (2)	−0.013 (2)	−0.012 (2)
C6	0.064 (3)	0.057 (2)	0.064 (3)	−0.014 (2)	0.004 (2)	0.0029 (19)
C7	0.050 (2)	0.0436 (19)	0.067 (2)	−0.0148 (16)	0.0027 (18)	−0.0048 (17)
C8	0.063 (3)	0.071 (3)	0.067 (3)	−0.025 (2)	0.015 (2)	−0.011 (2)
C9	0.046 (2)	0.064 (2)	0.053 (2)	−0.0173 (18)	0.0114 (16)	−0.0103 (18)
C10	0.064 (3)	0.084 (3)	0.073 (3)	−0.027 (2)	0.007 (2)	−0.016 (2)
C11	0.072 (3)	0.123 (5)	0.109 (4)	−0.049 (3)	0.013 (3)	−0.043 (4)
C12	0.094 (4)	0.093 (4)	0.131 (5)	−0.054 (3)	0.045 (4)	−0.041 (4)
C13	0.077 (3)	0.064 (3)	0.096 (4)	−0.010 (2)	0.034 (3)	−0.002 (3)
C14	0.051 (2)	0.071 (3)	0.062 (2)	−0.009 (2)	0.0118 (18)	−0.009 (2)
C15	0.066 (3)	0.079 (3)	0.071 (3)	−0.014 (2)	−0.001 (2)	0.002 (2)
C16	0.072 (3)	0.061 (3)	0.068 (3)	−0.012 (2)	0.006 (2)	0.009 (2)
C17	0.107 (4)	0.090 (4)	0.075 (3)	−0.023 (3)	0.018 (3)	−0.006 (3)
C18	0.141 (6)	0.104 (5)	0.112 (5)	−0.016 (4)	0.051 (5)	−0.009 (4)
C19	0.098 (5)	0.125 (6)	0.151 (7)	−0.022 (4)	0.055 (5)	0.004 (5)
C20	0.087 (4)	0.109 (5)	0.159 (6)	−0.044 (4)	0.003 (4)	0.040 (4)
C21	0.085 (3)	0.070 (3)	0.087 (3)	−0.028 (3)	−0.002 (3)	0.015 (2)
O1	0.067 (3)	0.091 (3)	0.085 (4)	−0.038 (3)	0.004 (2)	−0.030 (3)
O2	0.088 (4)	0.109 (4)	0.082 (3)	−0.047 (3)	0.008 (3)	−0.034 (3)
O3	0.102 (6)	0.073 (5)	0.103 (9)	−0.007 (4)	0.016 (5)	0.012 (5)
O4	0.123 (5)	0.105 (4)	0.096 (4)	−0.042 (4)	0.001 (3)	−0.019 (3)
C22	0.087 (7)	0.088 (5)	0.076 (4)	−0.041 (5)	−0.008 (5)	−0.011 (4)
C23	0.070 (7)	0.090 (6)	0.078 (4)	−0.040 (6)	−0.010 (4)	−0.017 (4)
C24	0.075 (7)	0.065 (6)	0.077 (3)	−0.027 (5)	−0.007 (4)	−0.013 (3)
C25	0.073 (3)	0.072 (4)	0.078 (3)	−0.018 (3)	−0.016 (2)	−0.006 (2)
C26	0.066 (3)	0.073 (4)	0.070 (3)	−0.020 (3)	−0.019 (2)	−0.006 (3)
C27	0.082 (7)	0.077 (6)	0.074 (3)	−0.017 (5)	−0.009 (4)	−0.015 (4)
C28	0.084 (6)	0.074 (6)	0.079 (4)	−0.019 (5)	−0.018 (4)	−0.003 (5)
C29	0.070 (4)	0.066 (5)	0.080 (4)	−0.018 (4)	−0.012 (3)	−0.027 (4)
C30	0.082 (4)	0.072 (6)	0.086 (6)	−0.027 (4)	−0.007 (4)	−0.006 (5)
C31	0.076 (4)	0.078 (5)	0.077 (5)	−0.024 (3)	−0.011 (3)	−0.006 (4)
C32	0.117 (6)	0.163 (10)	0.105 (8)	−0.066 (8)	−0.002 (5)	−0.021 (7)
O1'	0.067 (3)	0.091 (3)	0.085 (4)	−0.038 (3)	0.004 (2)	−0.030 (3)
O2'	0.088 (4)	0.109 (4)	0.082 (3)	−0.047 (3)	0.008 (3)	−0.034 (3)
O3'	0.102 (6)	0.073 (5)	0.103 (9)	−0.007 (4)	0.016 (5)	0.012 (5)
O4'	0.123 (5)	0.105 (4)	0.096 (4)	−0.042 (4)	0.001 (3)	−0.019 (3)
C22'	0.087 (7)	0.088 (5)	0.076 (4)	−0.041 (5)	−0.008 (5)	−0.011 (4)
C23'	0.070 (7)	0.090 (6)	0.078 (4)	−0.040 (6)	−0.010 (4)	−0.017 (4)
C24'	0.075 (7)	0.065 (6)	0.077 (3)	−0.027 (5)	−0.007 (4)	−0.013 (3)
C25'	0.073 (3)	0.072 (4)	0.078 (3)	−0.018 (3)	−0.016 (2)	−0.006 (2)
C26'	0.066 (3)	0.073 (4)	0.070 (3)	−0.020 (3)	−0.019 (2)	−0.006 (3)
C27'	0.082 (7)	0.077 (6)	0.074 (3)	−0.017 (5)	−0.009 (4)	−0.015 (4)
C28'	0.084 (6)	0.074 (6)	0.079 (4)	−0.019 (5)	−0.018 (4)	−0.003 (5)
C29'	0.070 (4)	0.066 (5)	0.080 (4)	−0.018 (4)	−0.012 (3)	−0.027 (4)
C30'	0.082 (4)	0.072 (6)	0.086 (6)	−0.027 (4)	−0.007 (4)	−0.006 (5)
C31'	0.076 (4)	0.078 (5)	0.077 (5)	−0.024 (3)	−0.011 (3)	−0.006 (4)
C32'	0.117 (6)	0.163 (10)	0.105 (8)	−0.066 (8)	−0.002 (5)	−0.021 (7)

Geometric parameters (Å, º) top

Sn1—O2'	2.103 (7)	O3—C25	1.236 (9)
Sn1—O1	2.108 (7)	O4—C29	1.348 (7)
Sn1—C15	2.150 (4)	O4—C32	1.385 (9)
Sn1—C8	2.155 (4)	C22—C23	1.460 (9)
Sn1—C1	2.165 (4)	C23—C24	1.457 (8)
Sn1—O1'	2.527 (6)	C23—H23A	0.9700
Cl1—C7	1.706 (2)	C23—H23B	0.9700
Cl2—C14	1.705 (3)	C24—C25	1.469 (9)
Cl3—C21	1.722 (3)	C24—H24A	0.9700
C1—C2	1.513 (4)	C24—H24B	0.9700
C1—H1A	0.9700	C25—C26	1.510 (8)
C1—H1B	0.9700	C26—C27	1.3900
C2—C3	1.3900	C26—C31	1.3900
C2—C7	1.3900	C27—C28	1.3900
C3—C4	1.3900	C27—H27	0.9300
C3—H3	0.9300	C28—C29	1.3900
C4—C5	1.3900	C28—H28	0.9300
C4—H4	0.9300	C29—C30	1.3900
C5—C6	1.3900	C30—C31	1.3900
C5—H5	0.9300	C30—H30	0.9300
C6—C7	1.3900	C31—H31	0.9300
C6—H6	0.9300	C32—H32A	0.9600
C8—C9	1.505 (4)	C32—H32B	0.9600
C8—H8A	0.9700	C32—H32C	0.9600
C8—H8B	0.9700	O1'—C22'	1.237 (8)
C9—C10	1.3900	O2'—C22'	1.279 (8)
C9—C14	1.3900	O3'—C25'	1.240 (9)
C10—C11	1.3900	O4'—C32'	1.354 (9)
C10—H10	0.9300	O4'—C29'	1.379 (7)
C11—C12	1.3900	C22'—C23'	1.487 (9)
C11—H11	0.9300	C23'—C24'	1.496 (8)
C12—C13	1.3900	C23'—H23C	0.9700
C12—H12	0.9300	C23'—H23D	0.9700
C13—C14	1.3900	C24'—C25'	1.475 (9)
C13—H13	0.9300	C24'—H24C	0.9700
C15—C16	1.504 (5)	C24'—H24D	0.9700
C15—H15A	0.9700	C25'—C26'	1.499 (8)
C15—H15B	0.9700	C26'—C27'	1.3900
C16—C17	1.3900	C26'—C31'	1.3900
C16—C21	1.3900	C27'—C28'	1.3900
C17—C18	1.3900	C27'—H27'	0.9300
C17—H17	0.9300	C28'—C29'	1.3900
C18—C19	1.3900	C28'—H28'	0.9300
C18—H18	0.9300	C29'—C30'	1.3900
C19—C20	1.3900	C30'—C31'	1.3900
C19—H19	0.9300	C30'—H30'	0.9300
C20—C21	1.3900	C31'—H31'	0.9300
C20—H20	0.9300	C32'—H32D	0.9600
O1—C22	1.251 (8)	C32'—H32E	0.9600
O2—C22	1.260 (8)	C32'—H32F	0.9600

O2'—Sn1—O1	35.4 (2)	C20—C21—Cl3	120.8 (3)
O2'—Sn1—C15	106.1 (2)	C16—C21—Cl3	119.2 (3)
O1—Sn1—C15	99.8 (2)	C22—O1—Sn1	109.7 (6)
O2'—Sn1—C8	89.2 (2)	C29—O4—C32	121.6 (11)
O1—Sn1—C8	122.1 (2)	O1—C22—O2	117.3 (8)
C15—Sn1—C8	115.29 (17)	O1—C22—C23	124.0 (8)
O2'—Sn1—C1	119.2 (2)	O2—C22—C23	118.7 (8)
O1—Sn1—C1	91.8 (2)	C24—C23—C22	114.9 (8)
C15—Sn1—C1	112.27 (17)	C24—C23—H23A	108.5
C8—Sn1—C1	112.93 (16)	C22—C23—H23A	108.5
O2'—Sn1—O1'	54.5 (2)	C24—C23—H23B	108.5
O1—Sn1—O1'	20.3 (2)	C22—C23—H23B	108.5
C15—Sn1—O1'	87.3 (2)	H23A—C23—H23B	107.5
C8—Sn1—O1'	142.43 (18)	C23—C24—C25	113.6 (8)
C1—Sn1—O1'	81.82 (17)	C23—C24—H24A	108.8
C2—C1—Sn1	113.2 (2)	C25—C24—H24A	108.8
C2—C1—H1A	108.9	C23—C24—H24B	108.8
Sn1—C1—H1A	108.9	C25—C24—H24B	108.8
C2—C1—H1B	108.9	H24A—C24—H24B	107.7
Sn1—C1—H1B	108.9	O3—C25—C24	125.8 (14)
H1A—C1—H1B	107.7	O3—C25—C26	107.8 (18)
C3—C2—C7	120.0	C24—C25—C26	126.4 (15)
C3—C2—C1	120.1 (2)	C27—C26—C31	120.0
C7—C2—C1	119.8 (2)	C27—C26—C25	113.4 (11)
C4—C3—C2	120.0	C31—C26—C25	126.5 (11)
C4—C3—H3	120.0	C26—C27—C28	120.0
C2—C3—H3	120.0	C26—C27—H27	120.0
C3—C4—C5	120.0	C28—C27—H27	120.0
C3—C4—H4	120.0	C29—C28—C27	120.0
C5—C4—H4	120.0	C29—C28—H28	120.0
C4—C5—C6	120.0	C27—C28—H28	120.0
C4—C5—H5	120.0	O4—C29—C28	118.5 (6)
C6—C5—H5	120.0	O4—C29—C30	121.4 (6)
C7—C6—C5	120.0	C28—C29—C30	120.0
C7—C6—H6	120.0	C29—C30—C31	120.0
C5—C6—H6	120.0	C29—C30—H30	120.0
C6—C7—C2	120.0	C31—C30—H30	120.0
C6—C7—Cl1	119.14 (15)	C30—C31—C26	120.0
C2—C7—Cl1	120.82 (15)	C30—C31—H31	120.0
C9—C8—Sn1	112.1 (2)	C26—C31—H31	120.0
C9—C8—H8A	109.2	C22'—O1'—Sn1	84.2 (5)
Sn1—C8—H8A	109.2	C22'—O2'—Sn1	103.2 (6)
C9—C8—H8B	109.2	C32'—O4'—C29'	117.2 (11)
Sn1—C8—H8B	109.2	O1'—C22'—O2'	117.8 (8)
H8A—C8—H8B	107.9	O1'—C22'—C23'	123.4 (8)
C10—C9—C14	120.0	O2'—C22'—C23'	118.8 (8)
C10—C9—C8	118.9 (3)	C22'—C23'—C24'	108.8 (7)
C14—C9—C8	121.1 (3)	C22'—C23'—H23C	109.9
C9—C10—C11	120.0	C24'—C23'—H23C	109.9
C9—C10—H10	120.0	C22'—C23'—H23D	109.9
C11—C10—H10	120.0	C24'—C23'—H23D	109.9
C12—C11—C10	120.0	H23C—C23'—H23D	108.3
C12—C11—H11	120.0	C25'—C24'—C23'	110.2 (8)
C10—C11—H11	120.0	C25'—C24'—H24C	109.6
C11—C12—C13	120.0	C23'—C24'—H24C	109.6
C11—C12—H12	120.0	C25'—C24'—H24D	109.6
C13—C12—H12	120.0	C23'—C24'—H24D	109.6
C12—C13—C14	120.0	H24C—C24'—H24D	108.1
C12—C13—H13	120.0	O3'—C25'—C24'	118.9 (14)
C14—C13—H13	120.0	O3'—C25'—C26'	128.2 (19)
C13—C14—C9	120.0	C24'—C25'—C26'	112.9 (15)
C13—C14—Cl2	118.7 (2)	C27'—C26'—C31'	120.0
C9—C14—Cl2	121.2 (2)	C27'—C26'—C25'	123.5 (11)
C16—C15—Sn1	110.4 (3)	C31'—C26'—C25'	116.5 (11)
C16—C15—H15A	109.6	C28'—C27'—C26'	120.0
Sn1—C15—H15A	109.6	C28'—C27'—H27'	120.0
C16—C15—H15B	109.6	C26'—C27'—H27'	120.0
Sn1—C15—H15B	109.6	C27'—C28'—C29'	120.0
H15A—C15—H15B	108.1	C27'—C28'—H28'	120.0
C17—C16—C21	120.0	C29'—C28'—H28'	120.0
C17—C16—C15	118.6 (3)	O4'—C29'—C28'	128.1 (6)
C21—C16—C15	121.3 (3)	O4'—C29'—C30'	111.9 (6)
C18—C17—C16	120.0	C28'—C29'—C30'	120.0
C18—C17—H17	120.0	C31'—C30'—C29'	120.0
C16—C17—H17	120.0	C31'—C30'—H30'	120.0
C17—C18—C19	120.0	C29'—C30'—H30'	120.0
C17—C18—H18	120.0	C30'—C31'—C26'	120.0
C19—C18—H18	120.0	C30'—C31'—H31'	120.0
C18—C19—C20	120.0	C26'—C31'—H31'	120.0
C18—C19—H19	120.0	O4'—C32'—H32D	109.5
C20—C19—H19	120.0	O4'—C32'—H32E	109.5
C21—C20—C19	120.0	H32D—C32'—H32E	109.5
C21—C20—H20	120.0	O4'—C32'—H32F	109.5
C19—C20—H20	120.0	H32D—C32'—H32F	109.5
C20—C21—C16	120.0	H32E—C32'—H32F	109.5

O2'—Sn1—C1—C2	109.8 (3)	Sn1—O1—C22—O2	5.3 (5)
O1—Sn1—C1—C2	133.3 (3)	Sn1—O1—C22—C23	−174.8 (5)
C15—Sn1—C1—C2	−125.3 (3)	O1—C22—C23—C24	26.9 (10)
C8—Sn1—C1—C2	7.1 (3)	O2—C22—C23—C24	−153.2 (10)
O1'—Sn1—C1—C2	151.1 (3)	C22—C23—C24—C25	68.8 (14)
Sn1—C1—C2—C3	108.5 (2)	C23—C24—C25—O3	−0.9 (14)
Sn1—C1—C2—C7	−69.5 (3)	C23—C24—C25—C26	179.3 (14)
C7—C2—C3—C4	0.0	O3—C25—C26—C27	−0.1 (11)
C1—C2—C3—C4	−178.1 (3)	C24—C25—C26—C27	179.8 (11)
C2—C3—C4—C5	0.0	O3—C25—C26—C31	−177.5 (17)
C3—C4—C5—C6	0.0	C24—C25—C26—C31	2.4 (17)
C4—C5—C6—C7	0.0	C31—C26—C27—C28	0.0
C5—C6—C7—C2	0.0	C25—C26—C27—C28	−177.6 (13)
C5—C6—C7—Cl1	−177.78 (19)	C26—C27—C28—C29	0.0
C3—C2—C7—C6	0.0	C32—O4—C29—C28	−176.6 (14)
C1—C2—C7—C6	178.1 (3)	C32—O4—C29—C30	6.1 (17)
C3—C2—C7—Cl1	177.74 (19)	C27—C28—C29—O4	−177.4 (10)
C1—C2—C7—Cl1	−4.2 (3)	C27—C28—C29—C30	0.0
O2'—Sn1—C8—C9	148.1 (3)	O4—C29—C30—C31	177.3 (10)
O1—Sn1—C8—C9	161.9 (3)	C28—C29—C30—C31	0.0
C15—Sn1—C8—C9	40.7 (3)	C29—C30—C31—C26	0.0
C1—Sn1—C8—C9	−90.2 (3)	C27—C26—C31—C30	0.0
O1'—Sn1—C8—C9	162.5 (3)	C25—C26—C31—C30	177.2 (15)
Sn1—C8—C9—C10	96.0 (3)	O2'—Sn1—O1'—C22'	−2.6 (3)
Sn1—C8—C9—C14	−81.6 (3)	O1—Sn1—O1'—C22'	−18.9 (7)
C14—C9—C10—C11	0.0	C15—Sn1—O1'—C22'	109.4 (3)
C8—C9—C10—C11	−177.6 (3)	C8—Sn1—O1'—C22'	−20.4 (5)
C9—C10—C11—C12	0.0	C1—Sn1—O1'—C22'	−137.7 (3)
C10—C11—C12—C13	0.0	O1—Sn1—O2'—C22'	12.3 (4)
C11—C12—C13—C14	0.0	C15—Sn1—O2'—C22'	−72.0 (4)
C12—C13—C14—C9	0.0	C8—Sn1—O2'—C22'	171.8 (4)
C12—C13—C14—Cl2	−177.9 (2)	C1—Sn1—O2'—C22'	55.8 (5)
C10—C9—C14—C13	0.0	O1'—Sn1—O2'—C22'	2.6 (3)
C8—C9—C14—C13	177.5 (3)	Sn1—O1'—C22'—O2'	3.9 (4)
C10—C9—C14—Cl2	177.9 (2)	Sn1—O1'—C22'—C23'	−175.9 (4)
C8—C9—C14—Cl2	−4.6 (3)	Sn1—O2'—C22'—O1'	−4.8 (5)
O2'—Sn1—C15—C16	123.7 (3)	Sn1—O2'—C22'—C23'	175.1 (5)
O1—Sn1—C15—C16	87.9 (4)	O1'—C22'—C23'—C24'	1.8 (9)
C8—Sn1—C15—C16	−139.4 (3)	O2'—C22'—C23'—C24'	−178.1 (9)
C1—Sn1—C15—C16	−8.1 (4)	C22'—C23'—C24'—C25'	65.6 (13)
O1'—Sn1—C15—C16	71.9 (3)	C23'—C24'—C25'—O3'	9.6 (14)
Sn1—C15—C16—C17	−99.6 (3)	C23'—C24'—C25'—C26'	−170.3 (14)
Sn1—C15—C16—C21	76.6 (3)	O3'—C25'—C26'—C27'	−11.1 (12)
C21—C16—C17—C18	0.0	C24'—C25'—C26'—C27'	168.8 (12)
C15—C16—C17—C18	176.2 (3)	O3'—C25'—C26'—C31'	168.3 (14)
C16—C17—C18—C19	0.0	C24'—C25'—C26'—C31'	−11.8 (14)
C17—C18—C19—C20	0.0	C31'—C26'—C27'—C28'	0.0
C18—C19—C20—C21	0.0	C25'—C26'—C27'—C28'	179.4 (15)
C19—C20—C21—C16	0.0	C26'—C27'—C28'—C29'	0.0
C19—C20—C21—Cl3	−178.7 (3)	C32'—O4'—C29'—C28'	−2.5 (17)
C17—C16—C21—C20	0.0	C32'—O4'—C29'—C30'	178.2 (14)
C15—C16—C21—C20	−176.1 (3)	C27'—C28'—C29'—O4'	−179.2 (11)
C17—C16—C21—Cl3	178.8 (3)	C27'—C28'—C29'—C30'	0.0
C15—C16—C21—Cl3	2.6 (3)	O4'—C29'—C30'—C31'	179.3 (9)
O2'—Sn1—O1—C22	−30.9 (4)	C28'—C29'—C30'—C31'	0.0
C15—Sn1—O1—C22	73.1 (4)	C29'—C30'—C31'—C26'	0.0
C8—Sn1—O1—C22	−55.2 (5)	C27'—C26'—C31'—C30'	0.0
C1—Sn1—O1—C22	−173.9 (4)	C25'—C26'—C31'—C30'	−179.4 (14)
O1'—Sn1—O1—C22	125.8 (10)

Experimental details

Crystal data
Chemical formula	[Sn(C₇H₆Cl)₃(C₁₁H₁₁O₄)]
M_r	702.59
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.4934 (6), 9.2077 (7), 21.3736 (16)
α, β, γ (°)	82.592 (1), 85.654 (1), 66.757 (1)
V (Å³)	1522.47 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.14
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.795, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14685, 6922, 5062
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.114, 1.03
No. of reflections	6922
No. of parameters	348
No. of restraints	116
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.41

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 and PS338/2009C) for supporting this study.

References

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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
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