rac-(3-Hydr­oxy-2-phenyl­propionato-κO)triphenyl­tin(IV)

Amini, M.M.; Hajiashrafi, T.; Kharat, A.N.; Ng, S.W.

doi:10.1107/S160053680803242X

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page m1403

doi:10.1107/S160053680803242X

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rac-(3-Hydroxy-2-phenylpropionato-κO)triphenyltin(IV)

Mostafa M. Amini,^a Taraneh Hajiashrafi,^b Ali Nemati Kharat ^b and Seik Weng Ng ^c ^*

^aDepartment of Chemistry, Shahid Beheshti University, Tehran, Iran, ^bSchool of Chemistry, College of Science, Tehran University, Tehran, Iran, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 7 October 2008; accepted 8 October 2008; online 15 October 2008)

The Sn^IV atom in the monomeric title compound, [Sn(C₆H₅)₃(C₉H₉O₃)] exists in a distorted SnC₃O tetrahedral geometry. In the crystal structure, inversion dimers arise from pairs of O—H⋯O hydrogen bonds.

Related literature

For reviews of organotin carboxylates, see: Tiekink (1991 , 1994 ).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₉H₉O₃)]
M_r = 515.15
Triclinic, $[P \overline 1]$
a = 9.3880 (2) Å
b = 9.4899 (2) Å
c = 14.3399 (2) Å
α = 90.087 (1)°
β = 103.664 (1)°
γ = 112.758 (1)°
V = 1138.58 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.15 mm⁻¹
T = 112 (2) K
0.39 × 0.32 × 0.31 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.663, T_max = 0.717
33531 measured reflections
6612 independent reflections
6339 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.054
S = 1.05
6612 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—O1	2.082 (1)
Sn1—C1	2.123 (1)
Sn1—C7	2.122 (1)
Sn1—C13	2.128 (1)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.84	1.98	2.819 (2)	175
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803242X/hb2813sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803242X/hb2813Isup2.hkl

checkCIF report

Comment top

The monomeric structure found for triphenyltin 2-hydroxy-3-phenylpropionate (Scheme I, Fig. 1) conforms to expectations based on the presence of bulky substituents (Tiekink, 1991, 1994). In the arbitrarily chosen asymmetric unit, C20 has R configuration, but crystal symmetry generates a racemic mixture. Selected geometrical data are given in Tables 1 and 2.

Related literature top

For reviews of organotin carboxylates, see: Tiekink (1991, 1994).

Experimental top

Triphenyltin hydroxide (1.0 g, 2.7 mmol) and d,l-tropic acid (0.45 g, 2.7 mmol) were heated in toluene (100 ml) in a Dean–Stark water-separator until all the water had been removed. The solvent was removed under reduced pressure to leave a white solid. The solid was recrystallized from mixture of chloroform, hexane and toluene (2:1:1 v/v) to give colorless blocks of (I), m.p. 385–386 K.

IR (KBr, cm^-1): 3449 (OH), 1627 (CO, asym), 1355 (CO, sym), 576, 601 (Sn—C). ¹H NMR (CDCl₃): 3.72–4.08 (m, 3H), 7.28–7.78 (20H, C₆H₅) p.p.m. ¹³C NMR (CDCl₃): 53.90 (CH), 65.08 (CH₂) 127.5–137.7 (C₆H₅) p.p.m. ¹¹⁹Sn NMR (CDCl₃): -83.1 p.p.m. Mass spectrum (m/e): 515 (M–1) [Ph₃SnO₂CCH(CH₂O)Ph]⁺, 439 (M–Ph) [Ph₃SnO₂CCH(CH₂OH)]⁺.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 70% probability level; hydrogen atoms are shown as spheres of arbitrary radius.

rac-(3-Hydroxy-2-phenylpropionato-κO)triphenyltin(IV) top

Crystal data top

[Sn(C₆H₅)₃(C₉H₉O₃)]	Z = 2
M_r = 515.15	F(000) = 520
Triclinic, P1	D_x = 1.503 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3880 (2) Å	Cell parameters from 9425 reflections
b = 9.4899 (2) Å	θ = 2.3–32.6°
c = 14.3399 (2) Å	µ = 1.15 mm⁻¹
α = 90.087 (1)°	T = 112 K
β = 103.664 (1)°	Block, colourless
γ = 112.758 (1)°	0.39 × 0.32 × 0.31 mm
V = 1138.58 (4) Å³

Data collection top

Bruker APEXII diffractometer	6612 independent reflections
Radiation source: medium-focus sealed tube	6339 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.663, T_max = 0.717	k = −13→13
33531 measured reflections	l = −19→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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.054	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0304P)² + 0.5255P] where P = (F_o² + 2F_c²)/3
6612 reflections	(Δ/σ)_max = 0.001
281 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Sn(C₆H₅)₃(C₉H₉O₃)]	γ = 112.758 (1)°
M_r = 515.15	V = 1138.58 (4) Å³
Triclinic, P1	Z = 2
a = 9.3880 (2) Å	Mo Kα radiation
b = 9.4899 (2) Å	µ = 1.15 mm⁻¹
c = 14.3399 (2) Å	T = 112 K
α = 90.087 (1)°	0.39 × 0.32 × 0.31 mm
β = 103.664 (1)°

Data collection top

Bruker APEXII diffractometer	6612 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	6339 reflections with I > 2σ(I)
T_min = 0.663, T_max = 0.717	R_int = 0.020
33531 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	0 restraints
wR(F²) = 0.054	H-atom parameters constrained
S = 1.05	Δρ_max = 0.64 e Å⁻³
6612 reflections	Δρ_min = −0.35 e Å⁻³
281 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.588742 (10)	0.636637 (10)	0.826066 (6)	0.02043 (3)
O1	0.74512 (13)	0.76508 (12)	0.74695 (7)	0.0268 (2)
O2	0.52531 (13)	0.67054 (13)	0.62949 (8)	0.0303 (2)
O3	0.71606 (16)	0.55344 (13)	0.51412 (10)	0.0394 (3)
H3	0.6449	0.4826	0.4734	0.059*
C1	0.54423 (16)	0.40565 (15)	0.78448 (9)	0.0222 (2)
C2	0.4203 (2)	0.28743 (18)	0.81068 (12)	0.0330 (3)
H2	0.3515	0.3111	0.8411	0.040*
C3	0.3973 (3)	0.1349 (2)	0.79226 (15)	0.0441 (4)
H3A	0.3129	0.0549	0.8102	0.053*
C4	0.4965 (2)	0.09935 (19)	0.74803 (13)	0.0400 (4)
H4	0.4812	−0.0048	0.7365	0.048*
C5	0.6186 (2)	0.21545 (19)	0.72034 (12)	0.0334 (3)
H5	0.6856	0.1908	0.6888	0.040*
C6	0.64278 (18)	0.36822 (17)	0.73878 (11)	0.0274 (3)
H6	0.7269	0.4476	0.7201	0.033*
C7	0.38486 (17)	0.68487 (16)	0.82227 (12)	0.0275 (3)
C8	0.25851 (18)	0.64580 (18)	0.73831 (13)	0.0333 (3)
H8	0.2686	0.6072	0.6802	0.040*
C9	0.1186 (2)	0.6635 (2)	0.74001 (16)	0.0425 (4)
H9	0.0335	0.6372	0.6831	0.051*
C10	0.1040 (2)	0.7191 (2)	0.82417 (19)	0.0480 (5)
H10	0.0082	0.7305	0.8252	0.058*
C11	0.2273 (2)	0.7587 (2)	0.90783 (18)	0.0458 (4)
H11	0.2160	0.7978	0.9655	0.055*
C12	0.3687 (2)	0.74112 (19)	0.90717 (14)	0.0358 (3)
H12	0.4531	0.7675	0.9644	0.043*
C13	0.76077 (16)	0.71155 (16)	0.96187 (10)	0.0231 (2)
C14	0.8361 (2)	0.61586 (19)	1.00105 (11)	0.0323 (3)
H14	0.8035	0.5161	0.9696	0.039*
C15	0.9590 (2)	0.6657 (2)	1.08601 (13)	0.0427 (4)
H15	1.0100	0.6001	1.1120	0.051*
C16	1.0063 (2)	0.8105 (2)	1.13220 (12)	0.0407 (4)
H16	1.0911	0.8451	1.1894	0.049*
C17	0.9304 (2)	0.9052 (2)	1.09543 (12)	0.0366 (3)
H17	0.9617	1.0038	1.1282	0.044*
C18	0.80848 (19)	0.85653 (17)	1.01073 (11)	0.0296 (3)
H18	0.7571	0.9223	0.9858	0.036*
C19	0.67104 (17)	0.73973 (16)	0.65568 (10)	0.0242 (2)
C20	0.77747 (17)	0.80071 (16)	0.58653 (10)	0.0240 (2)
H20	0.8833	0.7969	0.6167	0.029*
C21	0.7052 (2)	0.69608 (18)	0.49250 (11)	0.0310 (3)
H21A	0.5922	0.6808	0.4664	0.037*
H21B	0.7649	0.7415	0.4441	0.037*
C22	0.80597 (18)	0.96785 (16)	0.57297 (10)	0.0248 (3)
C23	0.6983 (2)	1.0097 (2)	0.50719 (13)	0.0394 (4)
H23	0.6010	0.9326	0.4703	0.047*
C24	0.7320 (3)	1.1637 (2)	0.49495 (15)	0.0481 (5)
H24	0.6583	1.1908	0.4490	0.058*
C25	0.8706 (3)	1.2768 (2)	0.54866 (16)	0.0439 (4)
H25	0.8932	1.3818	0.5399	0.053*
C26	0.9769 (2)	1.2367 (2)	0.61539 (17)	0.0444 (4)
H26	1.0719	1.3146	0.6538	0.053*
C27	0.9458 (2)	1.08338 (19)	0.62678 (13)	0.0348 (3)
H27	1.0212	1.0571	0.6719	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01937 (5)	0.01980 (5)	0.02268 (5)	0.00779 (3)	0.00640 (3)	0.00547 (3)
O1	0.0292 (5)	0.0248 (5)	0.0234 (4)	0.0066 (4)	0.0084 (4)	0.0063 (4)
O2	0.0288 (5)	0.0332 (5)	0.0280 (5)	0.0116 (4)	0.0067 (4)	0.0078 (4)
O3	0.0394 (6)	0.0223 (5)	0.0536 (7)	0.0103 (5)	0.0104 (6)	−0.0018 (5)
C1	0.0223 (6)	0.0217 (6)	0.0209 (5)	0.0075 (5)	0.0044 (4)	0.0048 (4)
C2	0.0350 (8)	0.0257 (7)	0.0369 (8)	0.0060 (6)	0.0173 (6)	0.0051 (6)
C3	0.0518 (11)	0.0232 (7)	0.0515 (10)	0.0028 (7)	0.0239 (9)	0.0067 (7)
C4	0.0555 (11)	0.0224 (7)	0.0398 (8)	0.0140 (7)	0.0108 (8)	0.0027 (6)
C5	0.0403 (8)	0.0319 (7)	0.0325 (7)	0.0193 (7)	0.0089 (6)	0.0017 (6)
C6	0.0268 (6)	0.0253 (6)	0.0306 (7)	0.0099 (5)	0.0093 (5)	0.0052 (5)
C7	0.0222 (6)	0.0217 (6)	0.0409 (8)	0.0092 (5)	0.0115 (6)	0.0083 (5)
C8	0.0246 (7)	0.0277 (7)	0.0467 (9)	0.0106 (6)	0.0073 (6)	0.0088 (6)
C9	0.0257 (7)	0.0337 (8)	0.0679 (12)	0.0139 (6)	0.0081 (8)	0.0113 (8)
C10	0.0301 (8)	0.0326 (8)	0.0894 (16)	0.0169 (7)	0.0221 (9)	0.0141 (9)
C11	0.0437 (10)	0.0322 (8)	0.0731 (13)	0.0175 (7)	0.0318 (10)	0.0050 (8)
C12	0.0335 (8)	0.0299 (7)	0.0485 (9)	0.0126 (6)	0.0186 (7)	0.0053 (7)
C13	0.0240 (6)	0.0240 (6)	0.0216 (5)	0.0086 (5)	0.0082 (5)	0.0050 (5)
C14	0.0395 (8)	0.0328 (7)	0.0267 (7)	0.0191 (7)	0.0040 (6)	0.0042 (6)
C15	0.0461 (10)	0.0534 (11)	0.0311 (8)	0.0281 (9)	0.0000 (7)	0.0070 (7)
C16	0.0326 (8)	0.0551 (11)	0.0251 (7)	0.0110 (8)	0.0016 (6)	0.0002 (7)
C17	0.0330 (8)	0.0321 (8)	0.0335 (8)	0.0014 (6)	0.0084 (6)	−0.0048 (6)
C18	0.0292 (7)	0.0246 (6)	0.0326 (7)	0.0075 (5)	0.0089 (6)	0.0032 (5)
C19	0.0301 (6)	0.0199 (6)	0.0240 (6)	0.0107 (5)	0.0083 (5)	0.0067 (5)
C20	0.0238 (6)	0.0228 (6)	0.0255 (6)	0.0083 (5)	0.0080 (5)	0.0061 (5)
C21	0.0367 (8)	0.0260 (7)	0.0300 (7)	0.0096 (6)	0.0133 (6)	0.0034 (5)
C22	0.0308 (7)	0.0214 (6)	0.0237 (6)	0.0090 (5)	0.0122 (5)	0.0063 (5)
C23	0.0438 (9)	0.0311 (8)	0.0345 (8)	0.0124 (7)	−0.0016 (7)	0.0065 (6)
C24	0.0682 (13)	0.0386 (9)	0.0429 (10)	0.0293 (9)	0.0105 (9)	0.0182 (8)
C25	0.0600 (11)	0.0237 (7)	0.0595 (11)	0.0159 (8)	0.0375 (10)	0.0160 (7)
C26	0.0344 (8)	0.0268 (8)	0.0681 (13)	0.0036 (6)	0.0210 (8)	−0.0049 (8)
C27	0.0306 (7)	0.0296 (7)	0.0431 (9)	0.0118 (6)	0.0075 (6)	−0.0005 (6)

Geometric parameters (Å, º) top

Sn1—O1	2.082 (1)	C12—H12	0.9500
Sn1—C1	2.123 (1)	C13—C18	1.399 (2)
Sn1—C7	2.122 (1)	C13—C14	1.397 (2)
Sn1—C13	2.128 (1)	C14—C15	1.397 (2)
O1—C19	1.3016 (17)	C14—H14	0.9500
O2—C19	1.2269 (18)	C15—C16	1.383 (3)
O3—C21	1.4254 (19)	C15—H15	0.9500
O3—H3	0.8400	C16—C17	1.383 (3)
C1—C6	1.397 (2)	C16—H16	0.9500
C1—C2	1.3970 (19)	C17—C18	1.390 (2)
C2—C3	1.394 (2)	C17—H17	0.9500
C2—H2	0.9500	C18—H18	0.9500
C3—C4	1.380 (3)	C19—C20	1.5294 (19)
C3—H3A	0.9500	C20—C22	1.5240 (19)
C4—C5	1.387 (3)	C20—C21	1.519 (2)
C4—H4	0.9500	C20—H20	1.0000
C5—C6	1.392 (2)	C21—H21A	0.9900
C5—H5	0.9500	C21—H21B	0.9900
C6—H6	0.9500	C22—C23	1.389 (2)
C7—C12	1.392 (2)	C22—C27	1.388 (2)
C7—C8	1.406 (2)	C23—C24	1.392 (2)
C8—C9	1.393 (2)	C23—H23	0.9500
C8—H8	0.9500	C24—C25	1.372 (3)
C9—C10	1.373 (3)	C24—H24	0.9500
C9—H9	0.9500	C25—C26	1.378 (3)
C10—C11	1.388 (3)	C25—H25	0.9500
C10—H10	0.9500	C26—C27	1.387 (2)
C11—C12	1.402 (2)	C26—H26	0.9500
C11—H11	0.9500	C27—H27	0.9500

O1—Sn1—C1	104.08 (5)	C15—C14—H14	119.7
O1—Sn1—C7	117.51 (5)	C13—C14—H14	119.7
O1—Sn1—C13	94.95 (5)	C16—C15—C14	119.92 (17)
C1—Sn1—C7	116.29 (5)	C16—C15—H15	120.0
C1—Sn1—C13	109.17 (5)	C14—C15—H15	120.0
C7—Sn1—C13	112.54 (6)	C15—C16—C17	120.18 (16)
C19—O1—Sn1	109.50 (9)	C15—C16—H16	119.9
C21—O3—H3	109.5	C17—C16—H16	119.9
C6—C1—C2	118.99 (13)	C18—C17—C16	120.14 (16)
C6—C1—Sn1	122.04 (10)	C18—C17—H17	119.9
C2—C1—Sn1	118.77 (11)	C16—C17—H17	119.9
C3—C2—C1	120.14 (15)	C17—C18—C13	120.60 (15)
C3—C2—H2	119.9	C17—C18—H18	119.7
C1—C2—H2	119.9	C13—C18—H18	119.7
C4—C3—C2	120.38 (16)	O2—C19—O1	120.51 (13)
C4—C3—H3A	119.8	O2—C19—C20	123.92 (13)
C2—C3—H3A	119.8	O1—C19—C20	115.57 (12)
C3—C4—C5	120.09 (15)	C22—C20—C21	113.37 (12)
C3—C4—H4	120.0	C22—C20—C19	110.50 (11)
C5—C4—H4	120.0	C21—C20—C19	109.60 (12)
C6—C5—C4	119.92 (15)	C22—C20—H20	107.7
C6—C5—H5	120.0	C21—C20—H20	107.7
C4—C5—H5	120.0	C19—C20—H20	107.7
C5—C6—C1	120.48 (14)	O3—C21—C20	106.66 (13)
C5—C6—H6	119.8	O3—C21—H21A	110.4
C1—C6—H6	119.8	C20—C21—H21A	110.4
C12—C7—C8	119.39 (15)	O3—C21—H21B	110.4
C12—C7—Sn1	119.13 (12)	C20—C21—H21B	110.4
C8—C7—Sn1	121.13 (12)	H21A—C21—H21B	108.6
C9—C8—C7	120.32 (17)	C23—C22—C27	118.32 (14)
C9—C8—H8	119.8	C23—C22—C20	122.50 (14)
C7—C8—H8	119.8	C27—C22—C20	119.17 (14)
C10—C9—C8	119.76 (18)	C22—C23—C24	120.45 (17)
C10—C9—H9	120.1	C22—C23—H23	119.8
C8—C9—H9	120.1	C24—C23—H23	119.8
C11—C10—C9	120.90 (17)	C25—C24—C23	120.65 (18)
C11—C10—H10	119.5	C25—C24—H24	119.7
C9—C10—H10	119.5	C23—C24—H24	119.7
C10—C11—C12	119.91 (19)	C24—C25—C26	119.37 (16)
C10—C11—H11	120.0	C24—C25—H25	120.3
C12—C11—H11	120.0	C26—C25—H25	120.3
C7—C12—C11	119.71 (18)	C25—C26—C27	120.40 (18)
C7—C12—H12	120.1	C25—C26—H26	119.8
C11—C12—H12	120.1	C27—C26—H26	119.8
C18—C13—C14	118.58 (14)	C26—C27—C22	120.79 (17)
C18—C13—Sn1	122.64 (11)	C26—C27—H27	119.6
C14—C13—Sn1	118.67 (11)	C22—C27—H27	119.6
C15—C14—C13	120.55 (16)

C1—Sn1—O1—C19	67.61 (10)	C7—Sn1—C13—C18	−45.80 (13)
C7—Sn1—O1—C19	−62.58 (11)	O1—Sn1—C13—C14	−99.31 (12)
C13—Sn1—O1—C19	178.80 (10)	C1—Sn1—C13—C14	7.46 (13)
O1—Sn1—C1—C6	17.13 (12)	C7—Sn1—C13—C14	138.15 (12)
C7—Sn1—C1—C6	148.04 (11)	C18—C13—C14—C15	−1.5 (2)
C13—Sn1—C1—C6	−83.32 (12)	Sn1—C13—C14—C15	174.73 (14)
O1—Sn1—C1—C2	−168.17 (11)	C13—C14—C15—C16	0.3 (3)
C7—Sn1—C1—C2	−37.26 (13)	C14—C15—C16—C17	1.1 (3)
C13—Sn1—C1—C2	91.39 (12)	C15—C16—C17—C18	−1.4 (3)
C6—C1—C2—C3	0.7 (2)	C16—C17—C18—C13	0.2 (2)
Sn1—C1—C2—C3	−174.13 (14)	C14—C13—C18—C17	1.2 (2)
C1—C2—C3—C4	0.0 (3)	Sn1—C13—C18—C17	−174.81 (12)
C2—C3—C4—C5	−0.9 (3)	Sn1—O1—C19—O2	11.24 (16)
C3—C4—C5—C6	1.1 (3)	Sn1—O1—C19—C20	−168.49 (9)
C4—C5—C6—C1	−0.4 (2)	O2—C19—C20—C22	93.95 (17)
C2—C1—C6—C5	−0.5 (2)	O1—C19—C20—C22	−86.33 (15)
Sn1—C1—C6—C5	174.18 (11)	O2—C19—C20—C21	−31.69 (19)
O1—Sn1—C7—C12	−116.37 (12)	O1—C19—C20—C21	148.03 (13)
C1—Sn1—C7—C12	119.36 (12)	C22—C20—C21—O3	168.43 (12)
C13—Sn1—C7—C12	−7.63 (14)	C19—C20—C21—O3	−67.59 (15)
O1—Sn1—C7—C8	70.48 (13)	C21—C20—C22—C23	39.8 (2)
C1—Sn1—C7—C8	−53.78 (13)	C19—C20—C22—C23	−83.70 (18)
C13—Sn1—C7—C8	179.23 (11)	C21—C20—C22—C27	−138.98 (15)
C12—C7—C8—C9	0.1 (2)	C19—C20—C22—C27	97.53 (16)
Sn1—C7—C8—C9	173.25 (12)	C27—C22—C23—C24	1.0 (3)
C7—C8—C9—C10	−0.1 (3)	C20—C22—C23—C24	−177.80 (17)
C8—C9—C10—C11	0.3 (3)	C22—C23—C24—C25	−1.1 (3)
C9—C10—C11—C12	−0.5 (3)	C23—C24—C25—C26	−0.1 (3)
C8—C7—C12—C11	−0.3 (2)	C24—C25—C26—C27	1.4 (3)
Sn1—C7—C12—C11	−173.55 (13)	C25—C26—C27—C22	−1.5 (3)
C10—C11—C12—C7	0.5 (3)	C23—C22—C27—C26	0.3 (3)
O1—Sn1—C13—C18	76.74 (12)	C20—C22—C27—C26	179.09 (15)
C1—Sn1—C13—C18	−176.49 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.84	1.98	2.819 (2)	175

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃(C₉H₉O₃)]
M_r	515.15
Crystal system, space group	Triclinic, P1
Temperature (K)	112
a, b, c (Å)	9.3880 (2), 9.4899 (2), 14.3399 (2)
α, β, γ (°)	90.087 (1), 103.664 (1), 112.758 (1)
V (Å³)	1138.58 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.15
Crystal size (mm)	0.39 × 0.32 × 0.31

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.663, 0.717
No. of measured, independent and observed [I > 2σ(I)] reflections	33531, 6612, 6339
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.054, 1.05
No. of reflections	6612
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.35

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Selected bond lengths (Å) top

Sn1—O1	2.082 (1)	Sn1—C7	2.122 (1)
Sn1—C1	2.123 (1)	Sn1—C13	2.128 (1)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.84	1.98	2.819 (2)	175

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We thank the University of Canterbury, New Zealand, for the diffraction measurements, and the Vice-President's Office for Research Affairs of Shahid Beheshti University and the University of Malaya for supporting this work.

References

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1–23. CrossRef CAS Web of Science Google Scholar
Tiekink, E. R. T. (1994). Trends Organomet. Chem. 1, 71–116. Google Scholar
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