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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): m1403.
Published online 2008 October 15. doi:  10.1107/S160053680803242X
PMCID: PMC2959787

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

Abstract

The SnIV 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 [triangle], 1994 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1403-scheme1.jpg

Experimental

Crystal data

  • [Sn(C6H5)3(C9H9O3)]
  • M r = 515.15
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1403-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.019
  • wR(F 2) = 0.054
  • S = 1.05
  • 6612 reflections
  • 281 parameters
  • H-atom parameters constrained
  • Δρmax = 0.64 e Å−3
  • Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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)]+.

Refinement

The hydrogen atoms were placed in calculated positions (C—H = 0.95–1.00 Å, O—H = 0.84 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier).

Figures

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

Crystal data

[Sn(C6H5)3(C9H9O3)]Z = 2
Mr = 515.15F(000) = 520
Triclinic, P1Dx = 1.503 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3880 (2) ÅCell parameters from 9425 reflections
b = 9.4899 (2) Åθ = 2.3–32.6°
c = 14.3399 (2) ŵ = 1.15 mm1
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

Bruker APEXII diffractometer6612 independent reflections
Radiation source: medium-focus sealed tube6339 reflections with I > 2σ(I)
graphiteRint = 0.020
[var phi] and ω scansθmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.663, Tmax = 0.717k = −13→13
33531 measured reflectionsl = −19→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.019Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0304P)2 + 0.5255P] where P = (Fo2 + 2Fc2)/3
6612 reflections(Δ/σ)max = 0.001
281 parametersΔρmax = 0.64 e Å3
0 restraintsΔρmin = −0.35 e Å3

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

xyzUiso*/Ueq
Sn10.588742 (10)0.636637 (10)0.826066 (6)0.02043 (3)
O10.74512 (13)0.76508 (12)0.74695 (7)0.0268 (2)
O20.52531 (13)0.67054 (13)0.62949 (8)0.0303 (2)
O30.71606 (16)0.55344 (13)0.51412 (10)0.0394 (3)
H30.64490.48260.47340.059*
C10.54423 (16)0.40565 (15)0.78448 (9)0.0222 (2)
C20.4203 (2)0.28743 (18)0.81068 (12)0.0330 (3)
H20.35150.31110.84110.040*
C30.3973 (3)0.1349 (2)0.79226 (15)0.0441 (4)
H3A0.31290.05490.81020.053*
C40.4965 (2)0.09935 (19)0.74803 (13)0.0400 (4)
H40.4812−0.00480.73650.048*
C50.6186 (2)0.21545 (19)0.72034 (12)0.0334 (3)
H50.68560.19080.68880.040*
C60.64278 (18)0.36822 (17)0.73878 (11)0.0274 (3)
H60.72690.44760.72010.033*
C70.38486 (17)0.68487 (16)0.82227 (12)0.0275 (3)
C80.25851 (18)0.64580 (18)0.73831 (13)0.0333 (3)
H80.26860.60720.68020.040*
C90.1186 (2)0.6635 (2)0.74001 (16)0.0425 (4)
H90.03350.63720.68310.051*
C100.1040 (2)0.7191 (2)0.82417 (19)0.0480 (5)
H100.00820.73050.82520.058*
C110.2273 (2)0.7587 (2)0.90783 (18)0.0458 (4)
H110.21600.79780.96550.055*
C120.3687 (2)0.74112 (19)0.90717 (14)0.0358 (3)
H120.45310.76750.96440.043*
C130.76077 (16)0.71155 (16)0.96187 (10)0.0231 (2)
C140.8361 (2)0.61586 (19)1.00105 (11)0.0323 (3)
H140.80350.51610.96960.039*
C150.9590 (2)0.6657 (2)1.08601 (13)0.0427 (4)
H151.01000.60011.11200.051*
C161.0063 (2)0.8105 (2)1.13220 (12)0.0407 (4)
H161.09110.84511.18940.049*
C170.9304 (2)0.9052 (2)1.09543 (12)0.0366 (3)
H170.96171.00381.12820.044*
C180.80848 (19)0.85653 (17)1.01073 (11)0.0296 (3)
H180.75710.92230.98580.036*
C190.67104 (17)0.73973 (16)0.65568 (10)0.0242 (2)
C200.77747 (17)0.80071 (16)0.58653 (10)0.0240 (2)
H200.88330.79690.61670.029*
C210.7052 (2)0.69608 (18)0.49250 (11)0.0310 (3)
H21A0.59220.68080.46640.037*
H21B0.76490.74150.44410.037*
C220.80597 (18)0.96785 (16)0.57297 (10)0.0248 (3)
C230.6983 (2)1.0097 (2)0.50719 (13)0.0394 (4)
H230.60100.93260.47030.047*
C240.7320 (3)1.1637 (2)0.49495 (15)0.0481 (5)
H240.65831.19080.44900.058*
C250.8706 (3)1.2768 (2)0.54866 (16)0.0439 (4)
H250.89321.38180.53990.053*
C260.9769 (2)1.2367 (2)0.61539 (17)0.0444 (4)
H261.07191.31460.65380.053*
C270.9458 (2)1.08338 (19)0.62678 (13)0.0348 (3)
H271.02121.05710.67190.042*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.01937 (5)0.01980 (5)0.02268 (5)0.00779 (3)0.00640 (3)0.00547 (3)
O10.0292 (5)0.0248 (5)0.0234 (4)0.0066 (4)0.0084 (4)0.0063 (4)
O20.0288 (5)0.0332 (5)0.0280 (5)0.0116 (4)0.0067 (4)0.0078 (4)
O30.0394 (6)0.0223 (5)0.0536 (7)0.0103 (5)0.0104 (6)−0.0018 (5)
C10.0223 (6)0.0217 (6)0.0209 (5)0.0075 (5)0.0044 (4)0.0048 (4)
C20.0350 (8)0.0257 (7)0.0369 (8)0.0060 (6)0.0173 (6)0.0051 (6)
C30.0518 (11)0.0232 (7)0.0515 (10)0.0028 (7)0.0239 (9)0.0067 (7)
C40.0555 (11)0.0224 (7)0.0398 (8)0.0140 (7)0.0108 (8)0.0027 (6)
C50.0403 (8)0.0319 (7)0.0325 (7)0.0193 (7)0.0089 (6)0.0017 (6)
C60.0268 (6)0.0253 (6)0.0306 (7)0.0099 (5)0.0093 (5)0.0052 (5)
C70.0222 (6)0.0217 (6)0.0409 (8)0.0092 (5)0.0115 (6)0.0083 (5)
C80.0246 (7)0.0277 (7)0.0467 (9)0.0106 (6)0.0073 (6)0.0088 (6)
C90.0257 (7)0.0337 (8)0.0679 (12)0.0139 (6)0.0081 (8)0.0113 (8)
C100.0301 (8)0.0326 (8)0.0894 (16)0.0169 (7)0.0221 (9)0.0141 (9)
C110.0437 (10)0.0322 (8)0.0731 (13)0.0175 (7)0.0318 (10)0.0050 (8)
C120.0335 (8)0.0299 (7)0.0485 (9)0.0126 (6)0.0186 (7)0.0053 (7)
C130.0240 (6)0.0240 (6)0.0216 (5)0.0086 (5)0.0082 (5)0.0050 (5)
C140.0395 (8)0.0328 (7)0.0267 (7)0.0191 (7)0.0040 (6)0.0042 (6)
C150.0461 (10)0.0534 (11)0.0311 (8)0.0281 (9)0.0000 (7)0.0070 (7)
C160.0326 (8)0.0551 (11)0.0251 (7)0.0110 (8)0.0016 (6)0.0002 (7)
C170.0330 (8)0.0321 (8)0.0335 (8)0.0014 (6)0.0084 (6)−0.0048 (6)
C180.0292 (7)0.0246 (6)0.0326 (7)0.0075 (5)0.0089 (6)0.0032 (5)
C190.0301 (6)0.0199 (6)0.0240 (6)0.0107 (5)0.0083 (5)0.0067 (5)
C200.0238 (6)0.0228 (6)0.0255 (6)0.0083 (5)0.0080 (5)0.0061 (5)
C210.0367 (8)0.0260 (7)0.0300 (7)0.0096 (6)0.0133 (6)0.0034 (5)
C220.0308 (7)0.0214 (6)0.0237 (6)0.0090 (5)0.0122 (5)0.0063 (5)
C230.0438 (9)0.0311 (8)0.0345 (8)0.0124 (7)−0.0016 (7)0.0065 (6)
C240.0682 (13)0.0386 (9)0.0429 (10)0.0293 (9)0.0105 (9)0.0182 (8)
C250.0600 (11)0.0237 (7)0.0595 (11)0.0159 (8)0.0375 (10)0.0160 (7)
C260.0344 (8)0.0268 (8)0.0681 (13)0.0036 (6)0.0210 (8)−0.0049 (8)
C270.0306 (7)0.0296 (7)0.0431 (9)0.0118 (6)0.0075 (6)−0.0005 (6)

Geometric parameters (Å, °)

Sn1—O12.082 (1)C12—H120.9500
Sn1—C12.123 (1)C13—C181.399 (2)
Sn1—C72.122 (1)C13—C141.397 (2)
Sn1—C132.128 (1)C14—C151.397 (2)
O1—C191.3016 (17)C14—H140.9500
O2—C191.2269 (18)C15—C161.383 (3)
O3—C211.4254 (19)C15—H150.9500
O3—H30.8400C16—C171.383 (3)
C1—C61.397 (2)C16—H160.9500
C1—C21.3970 (19)C17—C181.390 (2)
C2—C31.394 (2)C17—H170.9500
C2—H20.9500C18—H180.9500
C3—C41.380 (3)C19—C201.5294 (19)
C3—H3A0.9500C20—C221.5240 (19)
C4—C51.387 (3)C20—C211.519 (2)
C4—H40.9500C20—H201.0000
C5—C61.392 (2)C21—H21A0.9900
C5—H50.9500C21—H21B0.9900
C6—H60.9500C22—C231.389 (2)
C7—C121.392 (2)C22—C271.388 (2)
C7—C81.406 (2)C23—C241.392 (2)
C8—C91.393 (2)C23—H230.9500
C8—H80.9500C24—C251.372 (3)
C9—C101.373 (3)C24—H240.9500
C9—H90.9500C25—C261.378 (3)
C10—C111.388 (3)C25—H250.9500
C10—H100.9500C26—C271.387 (2)
C11—C121.402 (2)C26—H260.9500
C11—H110.9500C27—H270.9500
O1—Sn1—C1104.08 (5)C15—C14—H14119.7
O1—Sn1—C7117.51 (5)C13—C14—H14119.7
O1—Sn1—C1394.95 (5)C16—C15—C14119.92 (17)
C1—Sn1—C7116.29 (5)C16—C15—H15120.0
C1—Sn1—C13109.17 (5)C14—C15—H15120.0
C7—Sn1—C13112.54 (6)C15—C16—C17120.18 (16)
C19—O1—Sn1109.50 (9)C15—C16—H16119.9
C21—O3—H3109.5C17—C16—H16119.9
C6—C1—C2118.99 (13)C18—C17—C16120.14 (16)
C6—C1—Sn1122.04 (10)C18—C17—H17119.9
C2—C1—Sn1118.77 (11)C16—C17—H17119.9
C3—C2—C1120.14 (15)C17—C18—C13120.60 (15)
C3—C2—H2119.9C17—C18—H18119.7
C1—C2—H2119.9C13—C18—H18119.7
C4—C3—C2120.38 (16)O2—C19—O1120.51 (13)
C4—C3—H3A119.8O2—C19—C20123.92 (13)
C2—C3—H3A119.8O1—C19—C20115.57 (12)
C3—C4—C5120.09 (15)C22—C20—C21113.37 (12)
C3—C4—H4120.0C22—C20—C19110.50 (11)
C5—C4—H4120.0C21—C20—C19109.60 (12)
C6—C5—C4119.92 (15)C22—C20—H20107.7
C6—C5—H5120.0C21—C20—H20107.7
C4—C5—H5120.0C19—C20—H20107.7
C5—C6—C1120.48 (14)O3—C21—C20106.66 (13)
C5—C6—H6119.8O3—C21—H21A110.4
C1—C6—H6119.8C20—C21—H21A110.4
C12—C7—C8119.39 (15)O3—C21—H21B110.4
C12—C7—Sn1119.13 (12)C20—C21—H21B110.4
C8—C7—Sn1121.13 (12)H21A—C21—H21B108.6
C9—C8—C7120.32 (17)C23—C22—C27118.32 (14)
C9—C8—H8119.8C23—C22—C20122.50 (14)
C7—C8—H8119.8C27—C22—C20119.17 (14)
C10—C9—C8119.76 (18)C22—C23—C24120.45 (17)
C10—C9—H9120.1C22—C23—H23119.8
C8—C9—H9120.1C24—C23—H23119.8
C11—C10—C9120.90 (17)C25—C24—C23120.65 (18)
C11—C10—H10119.5C25—C24—H24119.7
C9—C10—H10119.5C23—C24—H24119.7
C10—C11—C12119.91 (19)C24—C25—C26119.37 (16)
C10—C11—H11120.0C24—C25—H25120.3
C12—C11—H11120.0C26—C25—H25120.3
C7—C12—C11119.71 (18)C25—C26—C27120.40 (18)
C7—C12—H12120.1C25—C26—H26119.8
C11—C12—H12120.1C27—C26—H26119.8
C18—C13—C14118.58 (14)C26—C27—C22120.79 (17)
C18—C13—Sn1122.64 (11)C26—C27—H27119.6
C14—C13—Sn1118.67 (11)C22—C27—H27119.6
C15—C14—C13120.55 (16)
C1—Sn1—O1—C1967.61 (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—C19178.80 (10)C1—Sn1—C13—C147.46 (13)
O1—Sn1—C1—C617.13 (12)C7—Sn1—C13—C14138.15 (12)
C7—Sn1—C1—C6148.04 (11)C18—C13—C14—C15−1.5 (2)
C13—Sn1—C1—C6−83.32 (12)Sn1—C13—C14—C15174.73 (14)
O1—Sn1—C1—C2−168.17 (11)C13—C14—C15—C160.3 (3)
C7—Sn1—C1—C2−37.26 (13)C14—C15—C16—C171.1 (3)
C13—Sn1—C1—C291.39 (12)C15—C16—C17—C18−1.4 (3)
C6—C1—C2—C30.7 (2)C16—C17—C18—C130.2 (2)
Sn1—C1—C2—C3−174.13 (14)C14—C13—C18—C171.2 (2)
C1—C2—C3—C40.0 (3)Sn1—C13—C18—C17−174.81 (12)
C2—C3—C4—C5−0.9 (3)Sn1—O1—C19—O211.24 (16)
C3—C4—C5—C61.1 (3)Sn1—O1—C19—C20−168.49 (9)
C4—C5—C6—C1−0.4 (2)O2—C19—C20—C2293.95 (17)
C2—C1—C6—C5−0.5 (2)O1—C19—C20—C22−86.33 (15)
Sn1—C1—C6—C5174.18 (11)O2—C19—C20—C21−31.69 (19)
O1—Sn1—C7—C12−116.37 (12)O1—C19—C20—C21148.03 (13)
C1—Sn1—C7—C12119.36 (12)C22—C20—C21—O3168.43 (12)
C13—Sn1—C7—C12−7.63 (14)C19—C20—C21—O3−67.59 (15)
O1—Sn1—C7—C870.48 (13)C21—C20—C22—C2339.8 (2)
C1—Sn1—C7—C8−53.78 (13)C19—C20—C22—C23−83.70 (18)
C13—Sn1—C7—C8179.23 (11)C21—C20—C22—C27−138.98 (15)
C12—C7—C8—C90.1 (2)C19—C20—C22—C2797.53 (16)
Sn1—C7—C8—C9173.25 (12)C27—C22—C23—C241.0 (3)
C7—C8—C9—C10−0.1 (3)C20—C22—C23—C24−177.80 (17)
C8—C9—C10—C110.3 (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—C271.4 (3)
Sn1—C7—C12—C11−173.55 (13)C25—C26—C27—C22−1.5 (3)
C10—C11—C12—C70.5 (3)C23—C22—C27—C260.3 (3)
O1—Sn1—C13—C1876.74 (12)C20—C22—C27—C26179.09 (15)
C1—Sn1—C13—C18−176.49 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.841.982.819 (2)175

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2813).

References

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