(4-Formyl-2-methoxy­phenolato)tris­(2-methyl-2-phenyl­prop­yl)tin(IV)

Dong, Y.

doi:10.1107/S1600536808003437

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page m450

doi:10.1107/S1600536808003437

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(4-Formyl-2-methoxyphenolato)tris(2-methyl-2-phenylpropyl)tin(IV)

Yan Dong ^a ^*

^aDepartment of Chemistry, Dezhou University, Dezhou 253023, People's Republic of China
^*Correspondence e-mail: dongyanchem@163.com

(Received 2 October 2007; accepted 31 January 2008; online 6 February 2008)

The Sn atom of the title compound, [Sn(C₁₀H₁₃)₃(C₈H₇O₃)], is four-coordinate and possesses a distorted SnOC₃ tetrahedral geometry.

Related literature

For related literature, see: Domingos & Sheldrick (1974 ); Yang et al. (2006 , 2007 ); Zhang et al. (2002 ).

Experimental

Crystal data

[Sn(C₁₀H₁₃)₃(C₈H₇O₃)]
M_r = 669.44
Monoclinic, P 2₁ /n
a = 9.7900 (13) Å
b = 33.761 (4) Å
c = 10.3073 (13) Å
β = 92.873 (2)°
V = 3402.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.79 mm⁻¹
T = 295 (2) K
0.20 × 0.16 × 0.08 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.859, T_max = 0.942
26454 measured reflections
6675 independent reflections
5252 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.099
S = 1.06
6675 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.96 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—O1	2.038 (3)
Sn1—C21	2.142 (4)
Sn1—C11	2.145 (4)
Sn1—C1	2.148 (4)

O1—Sn1—C21	106.72 (15)
O1—Sn1—C11	101.37 (13)
C21—Sn1—C11	118.18 (15)
O1—Sn1—C1	93.83 (14)
C21—Sn1—C1	115.01 (16)
C11—Sn1—C1	116.65 (16)

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003437/wn2240sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003437/wn2240Isup2.hkl

checkCIF report

Comment top

Little attention has been paid to the condensing reaction of tris(2-methyl-2-phenylpropyl)tin oxide, {[C₆H₅C(CH₃)₂CH₂]₃Sn}₂O, with phenols in the literature. In reported three structures, tris(2-methyl-2-phenylpropyl)tin pentachlorophenoate, 4-nitrophenolate, and 4-acetylphenolate (Zhang et al., 2002; Yang et al., 2006; Yang et al., 2007), the tin atom is four coordinated.

In the title compound, the Sn atom is also four-coordinate and possess a distorted SnOC₃ tetrahedral geometry (Fig. 1). This is different from Me₃SnOMe, in which almost planar trimethyltin groups are linked by two methoxy ligands forming infinite one-dimensional zigzag chains with nearly ideally trigonal-bipyramidal coordinated tin atom (Domingos & Sheldrick,1974), due to the crowding of the four bulky groups at the Sn atom in the title compound. The three Sn—C distances are almost equal [from 2.142 (4) to 2.148 (4) Å] and comparable with those [2.142 (2)–2.158 (2) and 2.144 (2)–2.157 (2) Å, respectively] in tris(2-methyl-2-phenylpropyl)tin 4-nitrophenolate and 4-acetylphenolate (Yang et al., 2006; Yang et al., 2007), but slightly longer than those [2.105 (4)–2.114 (4) Å] in tris(2-methyl-2-phenylpropyl)tin pentachlorophenoate (Zhang et al., 2002). The Sn—O dimension of the title compound is almost same as that [2.045 (2) and 2.041 (2) Å, respectively] of tris(2-methyl-2-phenylpropyl)tin 4-nitrophenolate and 4-acetylphenolate and shorter than that [2.103 (3) Å] found in tris(2-methyl-2-phenylpropyl)tin pentachlorophenoate.

Related literature top

For related literature, see: Domingos & Sheldrick (1974); Yang et al. (2006, 2007); Zhang et al. (2002).

Experimental top

The title compound was synthesized by condensing bis[tri(2-phenyl-2-methylpropyl)tin] oxide (1.05 g, 1 mmol) with 4-hydroxy-2-methoxybenzaldehyde (0.30 g, 2 mmol) in toluene (50 ml). Water was removed with a Dean-Stark water separator. The resulting clear solution was evaporated using a rotary evaporator. The white solid obtained was recrystallized from ethanol and crystals of title compound were obtained from chloroform-hexane (V/V, 1:1) by slow evaporation at room temperature (yield 81%, m.p. 388–389 K). Analysis, found: C 68.02, H 6.79%; calculated for C₃₈H₄₆O₃Sn: C 68.17, H 6.93%.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.

(4-Formyl-2-methoxyphenolato)tris(2-methyl-2-phenylpropyl)tin(IV) top

Crystal data top

[Sn(C₁₀H₁₃)₃(C₈H₇O₃)]	F(000) = 1392
M_r = 669.44	D_x = 1.307 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 4584 reflections
a = 9.7900 (13) Å	θ = 2.2–21.5°
b = 33.761 (4) Å	µ = 0.79 mm⁻¹
c = 10.3073 (13) Å	T = 295 K
β = 92.873 (2)°	Prism, colorless
V = 3402.5 (7) Å³	0.20 × 0.16 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEX area-detector diffractometer	6675 independent reflections
Radiation source: fine-focus sealed tube	5252 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
T_min = 0.859, T_max = 0.942	k = −41→41
26454 measured reflections	l = −12→12

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.023P)² + 3.2918P] where P = (F_o² + 2F_c²)/3
6675 reflections	(Δ/σ)_max = 0.001
379 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.96 e Å⁻³

Crystal data top

[Sn(C₁₀H₁₃)₃(C₈H₇O₃)]	V = 3402.5 (7) Å³
M_r = 669.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7900 (13) Å	µ = 0.79 mm⁻¹
b = 33.761 (4) Å	T = 295 K
c = 10.3073 (13) Å	0.20 × 0.16 × 0.08 mm
β = 92.873 (2)°

Data collection top

Bruker SMART APEX area-detector diffractometer	6675 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	5252 reflections with I > 2σ(I)
T_min = 0.859, T_max = 0.942	R_int = 0.055
26454 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.06	Δρ_max = 0.49 e Å⁻³
6675 reflections	Δρ_min = −0.96 e Å⁻³
379 parameters

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Sn1	0.63396 (3)	0.884454 (7)	0.76497 (2)	0.04078 (10)
O1	0.4361 (3)	0.89038 (8)	0.6964 (3)	0.0552 (7)
O2	0.3783 (3)	0.81358 (9)	0.7079 (3)	0.0634 (8)
O3	0.1355 (4)	0.78647 (13)	0.2522 (4)	0.0956 (12)
C1	0.6474 (5)	0.94423 (12)	0.8359 (4)	0.0560 (11)
H1A	0.5552	0.9532	0.8496	0.067*
H1B	0.6958	0.9435	0.9203	0.067*
C2	0.7167 (5)	0.97585 (12)	0.7536 (4)	0.0573 (11)
C3	0.6356 (5)	0.97925 (14)	0.6225 (5)	0.0789 (15)
H3A	0.5417	0.9852	0.6372	0.118*
H3B	0.6406	0.9546	0.5765	0.118*
H3C	0.6737	1.0000	0.5720	0.118*
C4	0.7058 (6)	1.01584 (14)	0.8247 (6)	0.0923 (18)
H4A	0.6112	1.0221	0.8344	0.138*
H4B	0.7473	1.0362	0.7750	0.138*
H4C	0.7521	1.0141	0.9088	0.138*
C5	0.8666 (5)	0.96629 (11)	0.7398 (5)	0.0565 (11)
C6	0.9267 (6)	0.96385 (13)	0.6211 (5)	0.0679 (13)
H6	0.8735	0.9685	0.5454	0.081*
C7	1.0630 (6)	0.95477 (15)	0.6121 (6)	0.0812 (16)
H7	1.0998	0.9530	0.5309	0.097*
C8	1.1438 (6)	0.94842 (16)	0.7202 (7)	0.0866 (17)
H8	1.2359	0.9424	0.7137	0.104*
C9	1.0890 (6)	0.95095 (16)	0.8388 (6)	0.0844 (17)
H9	1.1444	0.9468	0.9135	0.101*
C10	0.9512 (5)	0.95968 (13)	0.8497 (5)	0.0663 (13)
H10	0.9154	0.9611	0.9315	0.080*
C11	0.7350 (4)	0.87195 (11)	0.5896 (4)	0.0445 (9)
H11A	0.6692	0.8760	0.5173	0.053*
H11B	0.8067	0.8915	0.5816	0.053*
C12	0.7994 (4)	0.83075 (11)	0.5732 (4)	0.0436 (9)
C13	0.8845 (5)	0.83177 (14)	0.4515 (4)	0.0664 (13)
H13A	0.8260	0.8381	0.3767	0.100*
H13B	0.9259	0.8063	0.4395	0.100*
H13C	0.9546	0.8516	0.4623	0.100*
C14	0.6860 (5)	0.80029 (14)	0.5503 (5)	0.0675 (13)
H14A	0.6293	0.8078	0.4756	0.101*
H14B	0.6315	0.7991	0.6251	0.101*
H14C	0.7256	0.7748	0.5358	0.101*
C15	0.8936 (4)	0.82085 (11)	0.6905 (4)	0.0396 (9)
C16	0.9885 (4)	0.84824 (13)	0.7388 (4)	0.0575 (11)
H16	0.9940	0.8728	0.6984	0.069*
C17	1.0749 (5)	0.84018 (16)	0.8449 (5)	0.0782 (15)
H17	1.1370	0.8593	0.8753	0.094*
C18	1.0701 (6)	0.80462 (18)	0.9054 (5)	0.0783 (16)
H18	1.1284	0.7993	0.9773	0.094*
C19	0.9787 (5)	0.77666 (16)	0.8598 (5)	0.0741 (15)
H19	0.9750	0.7522	0.9009	0.089*
C20	0.8922 (4)	0.78446 (13)	0.7534 (4)	0.0579 (12)
H20	0.8316	0.7650	0.7230	0.069*
C21	0.6354 (5)	0.83972 (12)	0.9124 (4)	0.0547 (11)
H21A	0.5780	0.8181	0.8803	0.066*
H21B	0.7279	0.8296	0.9235	0.066*
C22	0.5881 (5)	0.85141 (13)	1.0473 (4)	0.0567 (11)
C23	0.4406 (5)	0.8664 (2)	1.0298 (5)	0.0923 (18)
H23A	0.3847	0.8463	0.9879	0.138*
H23B	0.4384	0.8898	0.9772	0.138*
H23C	0.4063	0.8723	1.1132	0.138*
C24	0.5910 (7)	0.81390 (17)	1.1334 (5)	0.102 (2)
H24A	0.5317	0.7942	1.0941	0.153*
H24B	0.5604	0.8205	1.2178	0.153*
H24C	0.6826	0.8038	1.1418	0.153*
C25	0.6838 (4)	0.88179 (13)	1.1135 (4)	0.0511 (10)
C26	0.8219 (5)	0.87993 (15)	1.1027 (5)	0.0671 (13)
H26	0.8587	0.8596	1.0544	0.081*
C27	0.9098 (6)	0.90794 (19)	1.1631 (6)	0.0865 (17)
H27	1.0037	0.9062	1.1545	0.104*
C28	0.8578 (9)	0.93748 (19)	1.2336 (6)	0.098 (2)
H28	0.9155	0.9564	1.2726	0.117*
C29	0.7232 (9)	0.93948 (19)	1.2471 (6)	0.108 (2)
H29	0.6876	0.9597	1.2965	0.130*
C30	0.6361 (6)	0.91187 (16)	1.1888 (5)	0.0819 (16)
H30	0.5427	0.9137	1.2007	0.098*
C31	0.3764 (4)	0.87261 (12)	0.5919 (4)	0.0480 (10)
C32	0.3435 (5)	0.89388 (13)	0.4813 (4)	0.0598 (12)
H32	0.3668	0.9206	0.4781	0.072*
C33	0.2766 (5)	0.87657 (15)	0.3742 (4)	0.0643 (13)
H33	0.2561	0.8914	0.2998	0.077*
C34	0.2407 (4)	0.83744 (15)	0.3786 (4)	0.0579 (12)
C35	0.1688 (5)	0.82004 (18)	0.2631 (5)	0.0753 (15)
H35	0.1480	0.8368	0.1932	0.090*
C36	0.2732 (4)	0.81543 (13)	0.4886 (4)	0.0545 (11)
H36	0.2502	0.7887	0.4904	0.065*
C37	0.3390 (4)	0.83231 (12)	0.5952 (4)	0.0476 (10)
C38	0.3435 (6)	0.77269 (15)	0.7182 (5)	0.0832 (16)
H38A	0.3760	0.7628	0.8015	0.125*
H38B	0.3851	0.7580	0.6509	0.125*
H38C	0.2460	0.7697	0.7093	0.125*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.04377 (16)	0.03930 (15)	0.03881 (15)	0.00142 (13)	−0.00246 (10)	−0.00157 (13)
O1	0.0413 (15)	0.0565 (18)	0.0669 (19)	0.0020 (13)	−0.0061 (14)	−0.0146 (15)
O2	0.062 (2)	0.0576 (19)	0.070 (2)	−0.0053 (15)	−0.0016 (16)	0.0036 (16)
O3	0.092 (3)	0.092 (3)	0.102 (3)	0.005 (2)	−0.014 (2)	−0.037 (2)
C1	0.065 (3)	0.046 (2)	0.057 (3)	0.002 (2)	−0.003 (2)	−0.012 (2)
C2	0.072 (3)	0.037 (2)	0.062 (3)	0.004 (2)	−0.013 (2)	0.002 (2)
C3	0.092 (4)	0.063 (3)	0.078 (4)	0.001 (3)	−0.021 (3)	0.017 (3)
C4	0.103 (4)	0.045 (3)	0.127 (5)	0.003 (3)	−0.010 (4)	−0.013 (3)
C5	0.072 (3)	0.033 (2)	0.063 (3)	−0.011 (2)	−0.009 (2)	0.003 (2)
C6	0.090 (4)	0.051 (3)	0.062 (3)	−0.011 (3)	−0.005 (3)	0.011 (2)
C7	0.092 (4)	0.062 (3)	0.091 (4)	−0.014 (3)	0.017 (4)	0.006 (3)
C8	0.073 (4)	0.063 (3)	0.123 (5)	−0.015 (3)	0.003 (4)	−0.015 (4)
C9	0.076 (4)	0.072 (4)	0.102 (5)	−0.008 (3)	−0.030 (3)	−0.010 (3)
C10	0.075 (3)	0.061 (3)	0.061 (3)	−0.014 (3)	−0.013 (3)	−0.004 (2)
C11	0.041 (2)	0.053 (2)	0.040 (2)	0.0021 (18)	0.0029 (17)	0.0052 (18)
C12	0.038 (2)	0.047 (2)	0.046 (2)	−0.0058 (17)	0.0017 (17)	−0.0083 (18)
C13	0.064 (3)	0.083 (3)	0.053 (3)	0.003 (3)	0.012 (2)	−0.010 (2)
C14	0.055 (3)	0.068 (3)	0.079 (3)	−0.014 (2)	−0.005 (2)	−0.018 (3)
C15	0.034 (2)	0.036 (2)	0.050 (2)	0.0048 (16)	0.0102 (17)	−0.0060 (17)
C16	0.057 (3)	0.049 (3)	0.065 (3)	0.004 (2)	−0.013 (2)	−0.001 (2)
C17	0.075 (3)	0.072 (4)	0.084 (4)	0.008 (3)	−0.031 (3)	−0.018 (3)
C18	0.084 (4)	0.091 (4)	0.058 (3)	0.031 (3)	−0.012 (3)	−0.001 (3)
C19	0.076 (4)	0.069 (3)	0.079 (4)	0.024 (3)	0.013 (3)	0.028 (3)
C20	0.050 (3)	0.045 (2)	0.078 (3)	0.002 (2)	0.006 (2)	0.007 (2)
C21	0.075 (3)	0.045 (2)	0.044 (2)	0.000 (2)	−0.004 (2)	0.0038 (19)
C22	0.062 (3)	0.064 (3)	0.044 (2)	−0.003 (2)	0.000 (2)	0.007 (2)
C23	0.055 (3)	0.155 (6)	0.068 (4)	−0.007 (3)	0.012 (3)	−0.005 (4)
C24	0.149 (6)	0.099 (4)	0.056 (3)	−0.046 (4)	−0.007 (3)	0.029 (3)
C25	0.061 (3)	0.057 (3)	0.035 (2)	0.007 (2)	0.0008 (18)	0.006 (2)
C26	0.063 (3)	0.075 (3)	0.063 (3)	0.007 (3)	−0.005 (2)	−0.004 (3)
C27	0.074 (4)	0.094 (4)	0.089 (4)	−0.011 (3)	−0.020 (3)	0.015 (4)
C28	0.135 (6)	0.080 (4)	0.076 (4)	−0.028 (4)	−0.023 (4)	−0.003 (3)
C29	0.149 (7)	0.088 (5)	0.087 (5)	−0.005 (5)	0.010 (5)	−0.035 (4)
C30	0.084 (4)	0.084 (4)	0.079 (4)	0.010 (3)	0.016 (3)	−0.018 (3)
C31	0.031 (2)	0.052 (2)	0.061 (3)	0.0034 (17)	0.0009 (18)	−0.009 (2)
C32	0.058 (3)	0.056 (3)	0.065 (3)	−0.001 (2)	−0.004 (2)	0.000 (2)
C33	0.060 (3)	0.078 (4)	0.054 (3)	0.004 (2)	−0.002 (2)	0.005 (2)
C34	0.040 (2)	0.076 (3)	0.057 (3)	0.008 (2)	−0.001 (2)	−0.014 (2)
C35	0.062 (3)	0.092 (4)	0.072 (4)	0.012 (3)	0.002 (3)	−0.028 (3)
C36	0.042 (2)	0.052 (3)	0.069 (3)	−0.0024 (19)	0.004 (2)	−0.009 (2)
C37	0.032 (2)	0.055 (3)	0.055 (3)	0.0045 (18)	−0.0007 (18)	−0.004 (2)
C38	0.096 (4)	0.064 (3)	0.090 (4)	−0.008 (3)	0.005 (3)	0.009 (3)

Geometric parameters (Å, º) top

Sn1—O1	2.038 (3)	C16—H16	0.9300
Sn1—C21	2.142 (4)	C17—C18	1.355 (7)
Sn1—C11	2.145 (4)	C17—H17	0.9300
Sn1—C1	2.148 (4)	C18—C19	1.368 (7)
O1—C31	1.341 (5)	C18—H18	0.9300
O2—C37	1.361 (5)	C19—C20	1.377 (6)
O2—C38	1.427 (5)	C19—H19	0.9300
O3—C35	1.183 (6)	C20—H20	0.9300
C1—C2	1.541 (6)	C21—C22	1.539 (6)
C1—H1A	0.9700	C21—H21A	0.9700
C1—H1B	0.9700	C21—H21B	0.9700
C2—C5	1.517 (6)	C22—C25	1.527 (6)
C2—C3	1.537 (6)	C22—C23	1.532 (6)
C2—C4	1.542 (6)	C22—C24	1.546 (6)
C3—H3A	0.9600	C23—H23A	0.9600
C3—H3B	0.9600	C23—H23B	0.9600
C3—H3C	0.9600	C23—H23C	0.9600
C4—H4A	0.9600	C24—H24A	0.9600
C4—H4B	0.9600	C24—H24B	0.9600
C4—H4C	0.9600	C24—H24C	0.9600
C5—C6	1.386 (6)	C25—C26	1.364 (6)
C5—C10	1.388 (6)	C25—C30	1.374 (6)
C6—C7	1.377 (7)	C26—C27	1.403 (7)
C6—H6	0.9300	C26—H26	0.9300
C7—C8	1.350 (7)	C27—C28	1.349 (8)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.362 (8)	C28—C29	1.334 (8)
C8—H8	0.9300	C28—H28	0.9300
C9—C10	1.390 (7)	C29—C30	1.381 (8)
C9—H9	0.9300	C29—H29	0.9300
C10—H10	0.9300	C30—H30	0.9300
C11—C12	1.540 (5)	C31—C32	1.373 (6)
C11—H11A	0.9700	C31—C37	1.410 (5)
C11—H11B	0.9700	C32—C33	1.384 (6)
C12—C15	1.520 (5)	C32—H32	0.9300
C12—C14	1.523 (5)	C33—C34	1.368 (6)
C12—C13	1.541 (5)	C33—H33	0.9300
C13—H13A	0.9600	C34—C36	1.380 (6)
C13—H13B	0.9600	C34—C35	1.474 (6)
C13—H13C	0.9600	C35—H35	0.9300
C14—H14A	0.9600	C36—C37	1.369 (5)
C14—H14B	0.9600	C36—H36	0.9300
C14—H14C	0.9600	C38—H38A	0.9600
C15—C16	1.386 (5)	C38—H38B	0.9600
C15—C20	1.390 (5)	C38—H38C	0.9600
C16—C17	1.376 (6)

O1—Sn1—C21	106.72 (15)	C18—C17—H17	119.8
O1—Sn1—C11	101.37 (13)	C16—C17—H17	119.8
C21—Sn1—C11	118.18 (15)	C17—C18—C19	119.3 (5)
O1—Sn1—C1	93.83 (14)	C17—C18—H18	120.3
C21—Sn1—C1	115.01 (16)	C19—C18—H18	120.3
C11—Sn1—C1	116.65 (16)	C18—C19—C20	120.5 (5)
C31—O1—Sn1	127.1 (2)	C18—C19—H19	119.7
C37—O2—C38	117.1 (4)	C20—C19—H19	119.7
C2—C1—Sn1	119.0 (3)	C19—C20—C15	121.4 (4)
C2—C1—H1A	107.6	C19—C20—H20	119.3
Sn1—C1—H1A	107.6	C15—C20—H20	119.3
C2—C1—H1B	107.6	C22—C21—Sn1	118.0 (3)
Sn1—C1—H1B	107.6	C22—C21—H21A	107.8
H1A—C1—H1B	107.0	Sn1—C21—H21A	107.8
C5—C2—C3	113.1 (4)	C22—C21—H21B	107.8
C5—C2—C1	111.0 (3)	Sn1—C21—H21B	107.8
C3—C2—C1	108.2 (4)	H21A—C21—H21B	107.2
C5—C2—C4	108.8 (4)	C25—C22—C23	112.7 (4)
C3—C2—C4	107.9 (4)	C25—C22—C21	111.7 (4)
C1—C2—C4	107.6 (4)	C23—C22—C21	107.6 (4)
C2—C3—H3A	109.5	C25—C22—C24	107.5 (4)
C2—C3—H3B	109.5	C23—C22—C24	109.1 (4)
H3A—C3—H3B	109.5	C21—C22—C24	108.1 (4)
C2—C3—H3C	109.5	C22—C23—H23A	109.5
H3A—C3—H3C	109.5	C22—C23—H23B	109.5
H3B—C3—H3C	109.5	H23A—C23—H23B	109.5
C2—C4—H4A	109.5	C22—C23—H23C	109.5
C2—C4—H4B	109.5	H23A—C23—H23C	109.5
H4A—C4—H4B	109.5	H23B—C23—H23C	109.5
C2—C4—H4C	109.5	C22—C24—H24A	109.5
H4A—C4—H4C	109.5	C22—C24—H24B	109.5
H4B—C4—H4C	109.5	H24A—C24—H24B	109.5
C6—C5—C10	116.7 (5)	C22—C24—H24C	109.5
C6—C5—C2	123.5 (4)	H24A—C24—H24C	109.5
C10—C5—C2	119.9 (4)	H24B—C24—H24C	109.5
C7—C6—C5	121.9 (5)	C26—C25—C30	116.5 (5)
C7—C6—H6	119.1	C26—C25—C22	121.4 (4)
C5—C6—H6	119.1	C30—C25—C22	122.0 (4)
C8—C7—C6	120.6 (6)	C25—C26—C27	121.4 (5)
C8—C7—H7	119.7	C25—C26—H26	119.3
C6—C7—H7	119.7	C27—C26—H26	119.3
C7—C8—C9	119.3 (6)	C28—C27—C26	119.9 (6)
C7—C8—H8	120.3	C28—C27—H27	120.1
C9—C8—H8	120.3	C26—C27—H27	120.1
C8—C9—C10	120.9 (5)	C29—C28—C27	119.7 (6)
C8—C9—H9	119.6	C29—C28—H28	120.2
C10—C9—H9	119.6	C27—C28—H28	120.2
C5—C10—C9	120.6 (5)	C28—C29—C30	120.8 (6)
C5—C10—H10	119.7	C28—C29—H29	119.6
C9—C10—H10	119.7	C30—C29—H29	119.6
C12—C11—Sn1	118.6 (3)	C25—C30—C29	121.6 (6)
C12—C11—H11A	107.7	C25—C30—H30	119.2
Sn1—C11—H11A	107.7	C29—C30—H30	119.2
C12—C11—H11B	107.7	O1—C31—C32	120.5 (4)
Sn1—C11—H11B	107.7	O1—C31—C37	121.1 (4)
H11A—C11—H11B	107.1	C32—C31—C37	118.3 (4)
C15—C12—C14	112.5 (3)	C31—C32—C33	121.6 (4)
C15—C12—C11	110.3 (3)	C31—C32—H32	119.2
C14—C12—C11	109.1 (3)	C33—C32—H32	119.2
C15—C12—C13	108.7 (3)	C34—C33—C32	119.6 (4)
C14—C12—C13	108.0 (3)	C34—C33—H33	120.2
C11—C12—C13	108.1 (3)	C32—C33—H33	120.2
C12—C13—H13A	109.5	C33—C34—C36	119.8 (4)
C12—C13—H13B	109.5	C33—C34—C35	118.1 (5)
H13A—C13—H13B	109.5	C36—C34—C35	122.0 (5)
C12—C13—H13C	109.5	O3—C35—C34	125.2 (6)
H13A—C13—H13C	109.5	O3—C35—H35	117.4
H13B—C13—H13C	109.5	C34—C35—H35	117.4
C12—C14—H14A	109.5	C37—C36—C34	121.0 (4)
C12—C14—H14B	109.5	C37—C36—H36	119.5
H14A—C14—H14B	109.5	C34—C36—H36	119.5
C12—C14—H14C	109.5	O2—C37—C36	126.4 (4)
H14A—C14—H14C	109.5	O2—C37—C31	114.0 (4)
H14B—C14—H14C	109.5	C36—C37—C31	119.7 (4)
C16—C15—C20	116.4 (4)	O2—C38—H38A	109.5
C16—C15—C12	120.5 (3)	O2—C38—H38B	109.5
C20—C15—C12	123.1 (4)	H38A—C38—H38B	109.5
C17—C16—C15	121.9 (4)	O2—C38—H38C	109.5
C17—C16—H16	119.1	H38A—C38—H38C	109.5
C15—C16—H16	119.1	H38B—C38—H38C	109.5
C18—C17—C16	120.5 (5)

C21—Sn1—O1—C31	−95.1 (3)	C16—C15—C20—C19	1.4 (6)
C11—Sn1—O1—C31	29.2 (4)	C12—C15—C20—C19	−179.7 (4)
C1—Sn1—O1—C31	147.4 (3)	O1—Sn1—C21—C22	−78.4 (3)
O1—Sn1—C1—C2	−99.6 (3)	C11—Sn1—C21—C22	168.4 (3)
C21—Sn1—C1—C2	149.9 (3)	C1—Sn1—C21—C22	24.2 (4)
C11—Sn1—C1—C2	5.2 (4)	Sn1—C21—C22—C25	−64.9 (4)
Sn1—C1—C2—C5	−63.6 (4)	Sn1—C21—C22—C23	59.2 (5)
Sn1—C1—C2—C3	61.1 (4)	Sn1—C21—C22—C24	177.0 (3)
Sn1—C1—C2—C4	177.5 (3)	C23—C22—C25—C26	−159.5 (4)
C3—C2—C5—C6	4.7 (6)	C21—C22—C25—C26	−38.2 (5)
C1—C2—C5—C6	126.6 (4)	C24—C22—C25—C26	80.2 (5)
C4—C2—C5—C6	−115.2 (5)	C23—C22—C25—C30	21.8 (6)
C3—C2—C5—C10	−175.7 (4)	C21—C22—C25—C30	143.1 (4)
C1—C2—C5—C10	−53.8 (5)	C24—C22—C25—C30	−98.5 (5)
C4—C2—C5—C10	64.4 (5)	C30—C25—C26—C27	−1.5 (7)
C10—C5—C6—C7	0.9 (6)	C22—C25—C26—C27	179.7 (4)
C2—C5—C6—C7	−179.5 (4)	C25—C26—C27—C28	0.1 (8)
C5—C6—C7—C8	−0.9 (8)	C26—C27—C28—C29	1.0 (9)
C6—C7—C8—C9	0.2 (8)	C27—C28—C29—C30	−0.6 (10)
C7—C8—C9—C10	0.4 (8)	C26—C25—C30—C29	1.9 (8)
C6—C5—C10—C9	−0.2 (6)	C22—C25—C30—C29	−179.3 (5)
C2—C5—C10—C9	−179.9 (4)	C28—C29—C30—C25	−0.9 (10)
C8—C9—C10—C5	−0.4 (8)	Sn1—O1—C31—C32	−108.0 (4)
O1—Sn1—C11—C12	−113.5 (3)	Sn1—O1—C31—C37	75.5 (4)
C21—Sn1—C11—C12	2.6 (4)	O1—C31—C32—C33	−177.2 (4)
C1—Sn1—C11—C12	146.3 (3)	C37—C31—C32—C33	−0.6 (6)
Sn1—C11—C12—C15	−52.1 (4)	C31—C32—C33—C34	0.7 (7)
Sn1—C11—C12—C14	72.0 (4)	C32—C33—C34—C36	−1.0 (7)
Sn1—C11—C12—C13	−170.8 (3)	C32—C33—C34—C35	179.7 (4)
C14—C12—C15—C16	−169.4 (4)	C33—C34—C35—O3	177.7 (5)
C11—C12—C15—C16	−47.3 (5)	C36—C34—C35—O3	−1.7 (8)
C13—C12—C15—C16	71.0 (5)	C33—C34—C36—C37	1.2 (6)
C14—C12—C15—C20	11.7 (5)	C35—C34—C36—C37	−179.4 (4)
C11—C12—C15—C20	133.8 (4)	C38—O2—C37—C36	−2.4 (6)
C13—C12—C15—C20	−107.8 (4)	C38—O2—C37—C31	179.8 (4)
C20—C15—C16—C17	−1.2 (6)	C34—C36—C37—O2	−178.8 (4)
C12—C15—C16—C17	179.8 (4)	C34—C36—C37—C31	−1.2 (6)
C15—C16—C17—C18	0.5 (8)	O1—C31—C37—O2	−4.7 (5)
C16—C17—C18—C19	0.2 (8)	C32—C31—C37—O2	178.8 (4)
C17—C18—C19—C20	0.0 (8)	O1—C31—C37—C36	177.4 (4)
C18—C19—C20—C15	−0.9 (7)	C32—C31—C37—C36	0.9 (6)

Experimental details

Crystal data
Chemical formula	[Sn(C₁₀H₁₃)₃(C₈H₇O₃)]
M_r	669.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	9.7900 (13), 33.761 (4), 10.3073 (13)
β (°)	92.873 (2)
V (Å³)	3402.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.20 × 0.16 × 0.08

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.859, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	26454, 6675, 5252
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.099, 1.06
No. of reflections	6675
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.96

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Selected geometric parameters (Å, º) top

Sn1—O1	2.038 (3)	Sn1—C11	2.145 (4)
Sn1—C21	2.142 (4)	Sn1—C1	2.148 (4)

O1—Sn1—C21	106.72 (15)	O1—Sn1—C1	93.83 (14)
O1—Sn1—C11	101.37 (13)	C21—Sn1—C1	115.01 (16)
C21—Sn1—C11	118.18 (15)	C11—Sn1—C1	116.65 (16)

Acknowledgements

The author thanks the Science Foundation of Dezhou University for supporting this work.

References

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