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Acta Cryst. (2007). E63, m2346    [ doi:10.1107/S160053680703961X ]

(Z)-Methyl 2-(1,3-dithian-2-ylidene)-4-(triphenylstannyl)but-3-enoate

C.-G. Zhu, D.-S. Zhu, X.-Y. Wu, Y.-H. Wang and D.-F. Du

Abstract top

In the title compound, [Sn(C6H5)3(C9H11O2S2)], the coordination geometry around the Sn atom is tetrahedral, involving three C atoms from three phenyl groups and one C atom from a methyl 2-(1,3-dithian-2-ylidene)but-3-enoate group. The conformation of the heterocyclic ring is twist-boat.

Comment top

In recent years there has been considerable interest in organotin compounds. Many organotin compounds are biologically active (Marcel, 2002). In this paper, the structure of the title compound is described.

As shown in Fig. 1, the coordination geometry around the Sn atom is tetrahedral, involving three C atoms from three phenyl groups and one C atom from a methy 2-(1,3-dithian-2-ylidene)but-3-enoate group (Table 1). The bond distances and angles are normal (Zhu et al., 2003).

Related literature top

For related literature, see: Marcel (2002); Zhu et al. (2003)

Experimental top

Methyl 2-(1,3-dithian-2-ylidene)but-3-enoate (10.70 g, 50 mmol) and dibenzoyl peroxide (0.100 g, 0.83 mmol) were added to dry ether (200 ml), and then triphenyltin hydride (21.94 g, 62.5 mmol) was added. The mixture was stirred for 30 h at room temperature. The ether was evaporated off and the residue was recrystallized three times from ethanol. Colorless single crystals were obtained by evaporation of ethanol at room temperature (17 g, yield 60%).

Refinement top

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93Å (CH), 0.97Å (CH2) and Uiso = 1.2Ueq(C), and with C—H = 0.96Å (CH3) and Uiso = 1.5Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound.
(Z)-Methyl 2-(1,3-dithian-2-ylidene)-4-(triphenylstannyl)but-3-enoate top
Crystal data top
[Sn(C6H5)3(C9H11O2S2)]F000 = 1144
Mr = 565.29Dx = 1.531 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3517 reflections
a = 8.170 (4) Åθ = 1.7–25.4º
b = 14.250 (7) ŵ = 1.23 mm−1
c = 21.171 (9) ÅT = 293 (2) K
β = 95.871 (9)ºBlock, colorless
V = 2452 (2) Å30.34 × 0.32 × 0.29 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4503 independent reflections
Radiation source: fine-focus sealed tube3086 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.033
T = 293(2) Kθmax = 25.4º
φ and ω scansθmin = 1.7º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.661, Tmax = 0.703k = −15→17
12531 measured reflectionsl = −20→25
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.075  w = 1/[σ2(Fo2) + (0.0317P)2 + 0.6236P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
4503 reflectionsΔρmax = 0.37 e Å−3
289 parametersΔρmin = −0.26 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Sn(C6H5)3(C9H11O2S2)]V = 2452 (2) Å3
Mr = 565.29Z = 4
Monoclinic, P21/cMo Kα
a = 8.170 (4) ŵ = 1.23 mm−1
b = 14.250 (7) ÅT = 293 (2) K
c = 21.171 (9) Å0.34 × 0.32 × 0.29 mm
β = 95.871 (9)º
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4503 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3086 reflections with I > 2σ(I)
Tmin = 0.661, Tmax = 0.703Rint = 0.033
12531 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.030289 parameters
wR(F2) = 0.075H-atom parameters constrained
S = 1.00Δρmax = 0.37 e Å−3
4503 reflectionsΔρmin = −0.26 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.14620 (3)0.750137 (16)0.024269 (10)0.05035 (9)
S1−0.33618 (14)0.63882 (7)0.09192 (5)0.0722 (3)
S2−0.20634 (13)0.70399 (7)0.22197 (4)0.0599 (2)
O1−0.0865 (3)0.95267 (16)0.11336 (11)0.0649 (7)
O2−0.0514 (4)0.87350 (17)0.20459 (12)0.0790 (8)
C1−0.0983 (4)0.7962 (2)0.00111 (15)0.0531 (8)
H1A−0.13340.8059−0.04160.064*
C2−0.2048 (4)0.8123 (2)0.04241 (15)0.0546 (9)
H2A−0.30840.83380.02660.066*
C3−0.1736 (4)0.7991 (2)0.11178 (14)0.0436 (7)
C4−0.0978 (4)0.8761 (2)0.14920 (17)0.0526 (8)
C5−0.0064 (6)1.0320 (3)0.1450 (2)0.0967 (15)
H5A−0.00341.08300.11550.145*
H5B0.10381.01510.16100.145*
H5C−0.06621.05080.17970.145*
C6−0.2290 (4)0.7211 (2)0.13986 (15)0.0470 (8)
C7−0.2896 (6)0.5317 (3)0.13250 (19)0.0846 (13)
H7A−0.34700.48170.10830.102*
H7B−0.17270.52010.13230.102*
C8−0.3302 (6)0.5244 (3)0.1989 (2)0.0867 (13)
H8A−0.42910.48690.19940.104*
H8B−0.24180.49110.22350.104*
C9−0.3562 (5)0.6145 (3)0.23040 (19)0.0770 (12)
H9A−0.35980.60270.27540.092*
H9B−0.46310.63860.21390.092*
C110.1669 (4)0.6234 (2)0.07770 (15)0.0514 (8)
C120.1930 (5)0.5402 (3)0.04814 (19)0.0772 (12)
H12A0.20030.53940.00460.093*
C130.2086 (6)0.4572 (3)0.0819 (2)0.0954 (15)
H13A0.22210.40100.06090.115*
C140.2042 (5)0.4576 (3)0.1457 (2)0.0854 (13)
H14A0.21850.40200.16860.102*
C150.1791 (5)0.5390 (3)0.17601 (19)0.0706 (11)
H15A0.17460.53920.21970.085*
C160.1602 (4)0.6215 (3)0.14231 (16)0.0594 (9)
H16A0.14240.67710.16360.071*
C210.2445 (4)0.7326 (2)−0.06506 (15)0.0489 (8)
C220.4102 (5)0.7381 (2)−0.06899 (17)0.0629 (10)
H22A0.48110.7445−0.03200.075*
C230.4741 (5)0.7344 (3)−0.1265 (2)0.0734 (12)
H23A0.58730.7384−0.12790.088*
C240.3745 (6)0.7250 (3)−0.18070 (19)0.0714 (12)
H24A0.41860.7238−0.21950.086*
C250.2125 (6)0.7174 (3)−0.17882 (17)0.0731 (12)
H25A0.14410.7093−0.21630.088*
C260.1451 (5)0.7214 (2)−0.12110 (17)0.0626 (10)
H26A0.03170.7166−0.12040.075*
C310.2921 (4)0.8562 (2)0.07341 (14)0.0486 (8)
C320.3052 (5)0.9437 (3)0.04708 (17)0.0722 (11)
H32A0.24240.95770.00910.087*
C330.4084 (6)1.0109 (3)0.0754 (2)0.0796 (12)
H33A0.41671.06890.05590.095*
C340.4985 (4)0.9933 (3)0.13154 (18)0.0621 (9)
H34A0.56701.03920.15110.075*
C350.4872 (4)0.9076 (3)0.15873 (16)0.0620 (9)
H35A0.54880.89460.19710.074*
C360.3853 (4)0.8396 (2)0.13000 (15)0.0566 (9)
H36A0.37950.78130.14940.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.05945 (16)0.05002 (14)0.04181 (13)−0.00129 (12)0.00632 (10)0.00262 (11)
S10.0930 (8)0.0571 (6)0.0637 (6)−0.0188 (5)−0.0064 (5)0.0009 (5)
S20.0757 (6)0.0560 (5)0.0489 (5)−0.0053 (5)0.0109 (4)0.0064 (4)
O10.0839 (18)0.0426 (14)0.0678 (16)−0.0125 (12)0.0061 (13)0.0067 (12)
O20.115 (2)0.0654 (18)0.0524 (15)−0.0256 (16)−0.0129 (15)0.0019 (13)
C10.059 (2)0.057 (2)0.0416 (18)−0.0067 (18)−0.0023 (16)0.0089 (16)
C20.049 (2)0.057 (2)0.056 (2)−0.0015 (17)−0.0036 (17)0.0101 (17)
C30.0457 (19)0.0410 (18)0.0441 (18)0.0045 (15)0.0039 (14)0.0035 (15)
C40.053 (2)0.046 (2)0.058 (2)−0.0027 (16)0.0064 (17)0.0038 (17)
C50.140 (4)0.052 (3)0.101 (3)−0.036 (3)0.025 (3)−0.008 (2)
C60.049 (2)0.0465 (19)0.0458 (18)0.0038 (14)0.0045 (15)0.0005 (14)
C70.120 (4)0.048 (2)0.088 (3)−0.005 (2)0.022 (3)−0.006 (2)
C80.125 (4)0.052 (3)0.087 (3)−0.011 (2)0.034 (3)0.002 (2)
C90.099 (3)0.063 (3)0.075 (3)−0.007 (2)0.037 (2)0.011 (2)
C110.052 (2)0.049 (2)0.053 (2)−0.0044 (16)0.0048 (16)0.0063 (16)
C120.109 (3)0.062 (3)0.060 (2)−0.003 (2)0.003 (2)0.001 (2)
C130.138 (4)0.051 (3)0.096 (4)0.003 (3)0.004 (3)0.002 (2)
C140.100 (4)0.066 (3)0.088 (3)−0.003 (2)−0.001 (3)0.026 (2)
C150.068 (3)0.081 (3)0.065 (2)−0.001 (2)0.011 (2)0.020 (2)
C160.060 (2)0.063 (2)0.057 (2)0.0037 (18)0.0154 (18)0.0087 (18)
C210.062 (2)0.040 (2)0.0447 (18)−0.0042 (15)0.0044 (16)0.0015 (13)
C220.064 (2)0.073 (3)0.051 (2)−0.002 (2)0.0013 (17)−0.0087 (18)
C230.072 (3)0.072 (3)0.080 (3)−0.008 (2)0.025 (2)−0.011 (2)
C240.107 (4)0.056 (3)0.055 (2)0.000 (2)0.028 (2)−0.0018 (18)
C250.108 (4)0.066 (3)0.042 (2)0.011 (2)−0.007 (2)−0.0076 (17)
C260.066 (2)0.061 (2)0.059 (2)0.0005 (18)−0.0020 (19)−0.0070 (17)
C310.056 (2)0.049 (2)0.0412 (18)0.0033 (16)0.0067 (15)−0.0031 (15)
C320.096 (3)0.055 (2)0.060 (2)−0.004 (2)−0.016 (2)0.0128 (19)
C330.108 (3)0.047 (2)0.081 (3)−0.007 (2)−0.005 (3)0.012 (2)
C340.063 (2)0.055 (2)0.069 (2)0.0017 (18)0.008 (2)−0.0118 (19)
C350.060 (2)0.072 (3)0.053 (2)0.008 (2)−0.0007 (17)−0.0062 (19)
C360.065 (2)0.051 (2)0.053 (2)0.0050 (18)0.0047 (17)0.0018 (17)
Geometric parameters (Å, °) top
Sn1—C12.113 (3)C12—H12A0.9300
Sn1—C112.128 (3)C13—C141.354 (5)
Sn1—C312.129 (3)C13—H13A0.9300
Sn1—C212.144 (3)C14—C151.351 (6)
S1—C61.729 (3)C14—H14A0.9300
S1—C71.774 (4)C15—C161.376 (5)
S2—C61.746 (3)C15—H15A0.9300
S2—C91.789 (4)C16—H16A0.9300
O1—C41.337 (4)C21—C221.367 (5)
O1—C51.437 (4)C21—C261.377 (5)
O2—C41.196 (4)C22—C231.373 (5)
C1—C21.315 (4)C22—H22A0.9300
C1—H1A0.9300C23—C241.344 (6)
C2—C31.477 (4)C23—H23A0.9300
C2—H2A0.9300C24—C251.333 (6)
C3—C61.360 (4)C24—H24A0.9300
C3—C41.455 (4)C25—C261.392 (5)
C5—H5A0.9600C25—H25A0.9300
C5—H5B0.9600C26—H26A0.9300
C5—H5C0.9600C31—C361.372 (4)
C7—C81.481 (5)C31—C321.374 (4)
C7—H7A0.9700C32—C331.373 (5)
C7—H7B0.9700C32—H32A0.9300
C8—C91.473 (5)C33—C341.356 (5)
C8—H8A0.9700C33—H33A0.9300
C8—H8B0.9700C34—C351.358 (5)
C9—H9A0.9700C34—H34A0.9300
C9—H9B0.9700C35—C361.377 (5)
C11—C121.368 (5)C35—H35A0.9300
C11—C161.375 (4)C36—H36A0.9300
C12—C131.381 (5)
C1—Sn1—C11114.15 (13)C11—C12—C13121.0 (4)
C1—Sn1—C31111.22 (13)C11—C12—H12A119.5
C11—Sn1—C31109.40 (13)C13—C12—H12A119.5
C1—Sn1—C21105.21 (13)C14—C13—C12120.2 (4)
C11—Sn1—C21110.69 (12)C14—C13—H13A119.9
C31—Sn1—C21105.80 (12)C12—C13—H13A119.9
C6—S1—C7103.22 (18)C15—C14—C13119.9 (4)
C6—S2—C9101.23 (18)C15—C14—H14A120.1
C4—O1—C5115.6 (3)C13—C14—H14A120.1
C2—C1—Sn1125.0 (3)C14—C15—C16120.1 (4)
C2—C1—H1A117.5C14—C15—H15A119.9
Sn1—C1—H1A117.5C16—C15—H15A119.9
C1—C2—C3125.5 (3)C11—C16—C15121.2 (4)
C1—C2—H2A117.3C11—C16—H16A119.4
C3—C2—H2A117.3C15—C16—H16A119.4
C6—C3—C4121.4 (3)C22—C21—C26117.1 (3)
C6—C3—C2120.5 (3)C22—C21—Sn1120.6 (2)
C4—C3—C2117.8 (3)C26—C21—Sn1122.2 (3)
O2—C4—O1123.3 (3)C21—C22—C23121.3 (4)
O2—C4—C3125.8 (3)C21—C22—H22A119.3
O1—C4—C3110.9 (3)C23—C22—H22A119.3
O1—C5—H5A109.5C24—C23—C22120.6 (4)
O1—C5—H5B109.5C24—C23—H23A119.7
H5A—C5—H5B109.5C22—C23—H23A119.7
O1—C5—H5C109.5C25—C24—C23119.9 (4)
H5A—C5—H5C109.5C25—C24—H24A120.0
H5B—C5—H5C109.5C23—C24—H24A120.0
C3—C6—S1118.0 (2)C24—C25—C26120.4 (4)
C3—C6—S2122.9 (2)C24—C25—H25A119.8
S1—C6—S2119.04 (19)C26—C25—H25A119.8
C8—C7—S1117.6 (3)C21—C26—C25120.6 (4)
C8—C7—H7A107.9C21—C26—H26A119.7
S1—C7—H7A107.9C25—C26—H26A119.7
C8—C7—H7B107.9C36—C31—C32116.8 (3)
S1—C7—H7B107.9C36—C31—Sn1122.5 (2)
H7A—C7—H7B107.2C32—C31—Sn1120.6 (3)
C9—C8—C7115.1 (3)C33—C32—C31121.7 (4)
C9—C8—H8A108.5C33—C32—H32A119.2
C7—C8—H8A108.5C31—C32—H32A119.2
C9—C8—H8B108.5C34—C33—C32120.6 (4)
C7—C8—H8B108.5C34—C33—H33A119.7
H8A—C8—H8B107.5C32—C33—H33A119.7
C8—C9—S2116.4 (3)C33—C34—C35118.9 (4)
C8—C9—H9A108.2C33—C34—H34A120.6
S2—C9—H9A108.2C35—C34—H34A120.6
C8—C9—H9B108.2C34—C35—C36120.6 (3)
S2—C9—H9B108.2C34—C35—H35A119.7
H9A—C9—H9B107.3C36—C35—H35A119.7
C12—C11—C16117.5 (3)C31—C36—C35121.4 (3)
C12—C11—Sn1120.0 (3)C31—C36—H36A119.3
C16—C11—Sn1122.4 (3)C35—C36—H36A119.3
Selected geometric parameters (Å, °) top
Sn1—C12.113 (3)Sn1—C312.129 (3)
Sn1—C112.128 (3)Sn1—C212.144 (3)
C1—Sn1—C11114.15 (13)C1—Sn1—C21105.21 (13)
C1—Sn1—C31111.22 (13)C11—Sn1—C21110.69 (12)
C11—Sn1—C31109.40 (13)C31—Sn1—C21105.80 (12)
Acknowledgements top

We thank the supporting certificate of the China Postdoctoral Science Foundation (No. 2005038561).

references
References top

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Marcel, G. (2002). Appl. Organomet. Chem. 16, 481–494.

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