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Acta Cryst. (2008). E64, m1403    [ doi:10.1107/S160053680803242X ]

rac-(3-Hydroxy-2-phenylpropionato-[kappa]O)triphenyltin(IV)

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

Abstract top

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.

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)]+.

Refinement top

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).

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
[Figure 1] 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
Mr = 515.15F(000) = 520
Triclinic, P1Dx = 1.503 Mg m−3
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 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 tube6339 reflections with I > 2σ(I)
graphiteRint = 0.020
φ 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 top
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 = 1.05 w = 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 Å−3
0 restraintsΔρmin = −0.35 e Å−3
Crystal data top
[Sn(C6H5)3(C9H9O3)]γ = 112.758 (1)°
Mr = 515.15V = 1138.58 (4) Å3
Triclinic, P1Z = 2
a = 9.3880 (2) ÅMo Kα radiation
b = 9.4899 (2) ŵ = 1.15 mm−1
c = 14.3399 (2) ÅT = 112 K
α = 90.087 (1)°0.39 × 0.32 × 0.31 mm
β = 103.664 (1)°
Data collection top
Bruker APEXII
diffractometer		6339 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		Rint = 0.020
Tmin = 0.663, Tmax = 0.717θmax = 30.0°
33531 measured reflectionsStandard reflections: 0
6612 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.019H-atom parameters constrained
wR(F2) = 0.054Δρmax = 0.64 e Å−3
S = 1.05Δρmin = −0.35 e Å−3
6612 reflectionsAbsolute structure: ?
281 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Selected geometric parameters (Å) top
Sn1—O12.082 (1)Sn1—C72.122 (1)
Sn1—C12.123 (1)Sn1—C132.128 (1)
Table 2
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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
References top

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