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

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

doi:10.1107/S160053680703961X

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(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

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703961X/hy2075sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680703961X/hy2075Isup2.hkl Contains datablock I

CCDC reference: 651149

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.030
wR factor = 0.075
Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C11    -C16           1.37 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C21    -C26           1.37 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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%).

Structure description top

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

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

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)]	F(000) = 1144
M_r = 565.29	D_x = 1.531 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3517 reflections
a = 8.170 (4) Å	θ = 1.7–25.4°
b = 14.250 (7) Å	µ = 1.23 mm⁻¹
c = 21.171 (9) Å	T = 293 K
β = 95.871 (9)°	Block, colorless
V = 2452 (2) Å³	0.34 × 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 tube	3086 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 25.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.661, T_max = 0.703	k = −15→17
12531 measured reflections	l = −20→25

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0317P)² + 0.6236P] where P = (F_o² + 2F_c²)/3
4503 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

[Sn(C₆H₅)₃(C₉H₁₁O₂S₂)]	V = 2452 (2) Å³
M_r = 565.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.170 (4) Å	µ = 1.23 mm⁻¹
b = 14.250 (7) Å	T = 293 K
c = 21.171 (9) Å	0.34 × 0.32 × 0.29 mm
β = 95.871 (9)°

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)
T_min = 0.661, T_max = 0.703	R_int = 0.033
12531 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.00	Δρ_max = 0.37 e Å⁻³
4503 reflections	Δρ_min = −0.27 e Å⁻³
289 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.14620 (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	−0.1334	0.8059	−0.0416	0.064*
C2	−0.2048 (4)	0.8123 (2)	0.04241 (15)	0.0546 (9)
H2A	−0.3084	0.8338	0.0266	0.066*
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	−0.0034	1.0830	0.1155	0.145*
H5B	0.1038	1.0151	0.1610	0.145*
H5C	−0.0662	1.0508	0.1797	0.145*
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	−0.3470	0.4817	0.1083	0.102*
H7B	−0.1727	0.5201	0.1323	0.102*
C8	−0.3302 (6)	0.5244 (3)	0.1989 (2)	0.0867 (13)
H8A	−0.4291	0.4869	0.1994	0.104*
H8B	−0.2418	0.4911	0.2235	0.104*
C9	−0.3562 (5)	0.6145 (3)	0.23040 (19)	0.0770 (12)
H9A	−0.3598	0.6027	0.2754	0.092*
H9B	−0.4631	0.6386	0.2139	0.092*
C11	0.1669 (4)	0.6234 (2)	0.07770 (15)	0.0514 (8)
C12	0.1930 (5)	0.5402 (3)	0.04814 (19)	0.0772 (12)
H12A	0.2003	0.5394	0.0046	0.093*
C13	0.2086 (6)	0.4572 (3)	0.0819 (2)	0.0954 (15)
H13A	0.2221	0.4010	0.0609	0.115*
C14	0.2042 (5)	0.4576 (3)	0.1457 (2)	0.0854 (13)
H14A	0.2185	0.4020	0.1686	0.102*
C15	0.1791 (5)	0.5390 (3)	0.17601 (19)	0.0706 (11)
H15A	0.1746	0.5392	0.2197	0.085*
C16	0.1602 (4)	0.6215 (3)	0.14231 (16)	0.0594 (9)
H16A	0.1424	0.6771	0.1636	0.071*
C21	0.2445 (4)	0.7326 (2)	−0.06506 (15)	0.0489 (8)
C22	0.4102 (5)	0.7381 (2)	−0.06899 (17)	0.0629 (10)
H22A	0.4811	0.7445	−0.0320	0.075*
C23	0.4741 (5)	0.7344 (3)	−0.1265 (2)	0.0734 (12)
H23A	0.5873	0.7384	−0.1279	0.088*
C24	0.3745 (6)	0.7250 (3)	−0.18070 (19)	0.0714 (12)
H24A	0.4186	0.7238	−0.2195	0.086*
C25	0.2125 (6)	0.7174 (3)	−0.17882 (17)	0.0731 (12)
H25A	0.1441	0.7093	−0.2163	0.088*
C26	0.1451 (5)	0.7214 (2)	−0.12110 (17)	0.0626 (10)
H26A	0.0317	0.7166	−0.1204	0.075*
C31	0.2921 (4)	0.8562 (2)	0.07341 (14)	0.0486 (8)
C32	0.3052 (5)	0.9437 (3)	0.04708 (17)	0.0722 (11)
H32A	0.2424	0.9577	0.0091	0.087*
C33	0.4084 (6)	1.0109 (3)	0.0754 (2)	0.0796 (12)
H33A	0.4167	1.0689	0.0559	0.095*
C34	0.4985 (4)	0.9933 (3)	0.13154 (18)	0.0621 (9)
H34A	0.5670	1.0392	0.1511	0.075*
C35	0.4872 (4)	0.9076 (3)	0.15873 (16)	0.0620 (9)
H35A	0.5488	0.8946	0.1971	0.074*
C36	0.3853 (4)	0.8396 (2)	0.13000 (15)	0.0566 (9)
H36A	0.3795	0.7813	0.1494	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.05945 (16)	0.05002 (14)	0.04181 (13)	−0.00129 (12)	0.00632 (10)	0.00262 (11)
S1	0.0930 (8)	0.0571 (6)	0.0637 (6)	−0.0188 (5)	−0.0064 (5)	0.0009 (5)
S2	0.0757 (6)	0.0560 (5)	0.0489 (5)	−0.0053 (5)	0.0109 (4)	0.0064 (4)
O1	0.0839 (18)	0.0426 (14)	0.0678 (16)	−0.0125 (12)	0.0061 (13)	0.0067 (12)
O2	0.115 (2)	0.0654 (18)	0.0524 (15)	−0.0256 (16)	−0.0129 (15)	0.0019 (13)
C1	0.059 (2)	0.057 (2)	0.0416 (18)	−0.0067 (18)	−0.0023 (16)	0.0089 (16)
C2	0.049 (2)	0.057 (2)	0.056 (2)	−0.0015 (17)	−0.0036 (17)	0.0101 (17)
C3	0.0457 (19)	0.0410 (18)	0.0441 (18)	0.0045 (15)	0.0039 (14)	0.0035 (15)
C4	0.053 (2)	0.046 (2)	0.058 (2)	−0.0027 (16)	0.0064 (17)	0.0038 (17)
C5	0.140 (4)	0.052 (3)	0.101 (3)	−0.036 (3)	0.025 (3)	−0.008 (2)
C6	0.049 (2)	0.0465 (19)	0.0458 (18)	0.0038 (14)	0.0045 (15)	0.0005 (14)
C7	0.120 (4)	0.048 (2)	0.088 (3)	−0.005 (2)	0.022 (3)	−0.006 (2)
C8	0.125 (4)	0.052 (3)	0.087 (3)	−0.011 (2)	0.034 (3)	0.002 (2)
C9	0.099 (3)	0.063 (3)	0.075 (3)	−0.007 (2)	0.037 (2)	0.011 (2)
C11	0.052 (2)	0.049 (2)	0.053 (2)	−0.0044 (16)	0.0048 (16)	0.0063 (16)
C12	0.109 (3)	0.062 (3)	0.060 (2)	−0.003 (2)	0.003 (2)	0.001 (2)
C13	0.138 (4)	0.051 (3)	0.096 (4)	0.003 (3)	0.004 (3)	0.002 (2)
C14	0.100 (4)	0.066 (3)	0.088 (3)	−0.003 (2)	−0.001 (3)	0.026 (2)
C15	0.068 (3)	0.081 (3)	0.065 (2)	−0.001 (2)	0.011 (2)	0.020 (2)
C16	0.060 (2)	0.063 (2)	0.057 (2)	0.0037 (18)	0.0154 (18)	0.0087 (18)
C21	0.062 (2)	0.040 (2)	0.0447 (18)	−0.0042 (15)	0.0044 (16)	0.0015 (13)
C22	0.064 (2)	0.073 (3)	0.051 (2)	−0.002 (2)	0.0013 (17)	−0.0087 (18)
C23	0.072 (3)	0.072 (3)	0.080 (3)	−0.008 (2)	0.025 (2)	−0.011 (2)
C24	0.107 (4)	0.056 (3)	0.055 (2)	0.000 (2)	0.028 (2)	−0.0018 (18)
C25	0.108 (4)	0.066 (3)	0.042 (2)	0.011 (2)	−0.007 (2)	−0.0076 (17)
C26	0.066 (2)	0.061 (2)	0.059 (2)	0.0005 (18)	−0.0020 (19)	−0.0070 (17)
C31	0.056 (2)	0.049 (2)	0.0412 (18)	0.0033 (16)	0.0067 (15)	−0.0031 (15)
C32	0.096 (3)	0.055 (2)	0.060 (2)	−0.004 (2)	−0.016 (2)	0.0128 (19)
C33	0.108 (3)	0.047 (2)	0.081 (3)	−0.007 (2)	−0.005 (3)	0.012 (2)
C34	0.063 (2)	0.055 (2)	0.069 (2)	0.0017 (18)	0.008 (2)	−0.0118 (19)
C35	0.060 (2)	0.072 (3)	0.053 (2)	0.008 (2)	−0.0007 (17)	−0.0062 (19)
C36	0.065 (2)	0.051 (2)	0.053 (2)	0.0050 (18)	0.0047 (17)	0.0018 (17)

Geometric parameters (Å, º) top

Sn1—C1	2.113 (3)	C12—H12A	0.9300
Sn1—C11	2.128 (3)	C13—C14	1.354 (5)
Sn1—C31	2.129 (3)	C13—H13A	0.9300
Sn1—C21	2.144 (3)	C14—C15	1.351 (6)
S1—C6	1.729 (3)	C14—H14A	0.9300
S1—C7	1.774 (4)	C15—C16	1.376 (5)
S2—C6	1.746 (3)	C15—H15A	0.9300
S2—C9	1.789 (4)	C16—H16A	0.9300
O1—C4	1.337 (4)	C21—C22	1.367 (5)
O1—C5	1.437 (4)	C21—C26	1.377 (5)
O2—C4	1.196 (4)	C22—C23	1.373 (5)
C1—C2	1.315 (4)	C22—H22A	0.9300
C1—H1A	0.9300	C23—C24	1.344 (6)
C2—C3	1.477 (4)	C23—H23A	0.9300
C2—H2A	0.9300	C24—C25	1.333 (6)
C3—C6	1.360 (4)	C24—H24A	0.9300
C3—C4	1.455 (4)	C25—C26	1.392 (5)
C5—H5A	0.9600	C25—H25A	0.9300
C5—H5B	0.9600	C26—H26A	0.9300
C5—H5C	0.9600	C31—C36	1.372 (4)
C7—C8	1.481 (5)	C31—C32	1.374 (4)
C7—H7A	0.9700	C32—C33	1.373 (5)
C7—H7B	0.9700	C32—H32A	0.9300
C8—C9	1.473 (5)	C33—C34	1.356 (5)
C8—H8A	0.9700	C33—H33A	0.9300
C8—H8B	0.9700	C34—C35	1.358 (5)
C9—H9A	0.9700	C34—H34A	0.9300
C9—H9B	0.9700	C35—C36	1.377 (5)
C11—C12	1.368 (5)	C35—H35A	0.9300
C11—C16	1.375 (4)	C36—H36A	0.9300
C12—C13	1.381 (5)

C1—Sn1—C11	114.15 (13)	C11—C12—C13	121.0 (4)
C1—Sn1—C31	111.22 (13)	C11—C12—H12A	119.5
C11—Sn1—C31	109.40 (13)	C13—C12—H12A	119.5
C1—Sn1—C21	105.21 (13)	C14—C13—C12	120.2 (4)
C11—Sn1—C21	110.69 (12)	C14—C13—H13A	119.9
C31—Sn1—C21	105.80 (12)	C12—C13—H13A	119.9
C6—S1—C7	103.22 (18)	C15—C14—C13	119.9 (4)
C6—S2—C9	101.23 (18)	C15—C14—H14A	120.1
C4—O1—C5	115.6 (3)	C13—C14—H14A	120.1
C2—C1—Sn1	125.0 (3)	C14—C15—C16	120.1 (4)
C2—C1—H1A	117.5	C14—C15—H15A	119.9
Sn1—C1—H1A	117.5	C16—C15—H15A	119.9
C1—C2—C3	125.5 (3)	C11—C16—C15	121.2 (4)
C1—C2—H2A	117.3	C11—C16—H16A	119.4
C3—C2—H2A	117.3	C15—C16—H16A	119.4
C6—C3—C4	121.4 (3)	C22—C21—C26	117.1 (3)
C6—C3—C2	120.5 (3)	C22—C21—Sn1	120.6 (2)
C4—C3—C2	117.8 (3)	C26—C21—Sn1	122.2 (3)
O2—C4—O1	123.3 (3)	C21—C22—C23	121.3 (4)
O2—C4—C3	125.8 (3)	C21—C22—H22A	119.3
O1—C4—C3	110.9 (3)	C23—C22—H22A	119.3
O1—C5—H5A	109.5	C24—C23—C22	120.6 (4)
O1—C5—H5B	109.5	C24—C23—H23A	119.7
H5A—C5—H5B	109.5	C22—C23—H23A	119.7
O1—C5—H5C	109.5	C25—C24—C23	119.9 (4)
H5A—C5—H5C	109.5	C25—C24—H24A	120.0
H5B—C5—H5C	109.5	C23—C24—H24A	120.0
C3—C6—S1	118.0 (2)	C24—C25—C26	120.4 (4)
C3—C6—S2	122.9 (2)	C24—C25—H25A	119.8
S1—C6—S2	119.04 (19)	C26—C25—H25A	119.8
C8—C7—S1	117.6 (3)	C21—C26—C25	120.6 (4)
C8—C7—H7A	107.9	C21—C26—H26A	119.7
S1—C7—H7A	107.9	C25—C26—H26A	119.7
C8—C7—H7B	107.9	C36—C31—C32	116.8 (3)
S1—C7—H7B	107.9	C36—C31—Sn1	122.5 (2)
H7A—C7—H7B	107.2	C32—C31—Sn1	120.6 (3)
C9—C8—C7	115.1 (3)	C33—C32—C31	121.7 (4)
C9—C8—H8A	108.5	C33—C32—H32A	119.2
C7—C8—H8A	108.5	C31—C32—H32A	119.2
C9—C8—H8B	108.5	C34—C33—C32	120.6 (4)
C7—C8—H8B	108.5	C34—C33—H33A	119.7
H8A—C8—H8B	107.5	C32—C33—H33A	119.7
C8—C9—S2	116.4 (3)	C33—C34—C35	118.9 (4)
C8—C9—H9A	108.2	C33—C34—H34A	120.6
S2—C9—H9A	108.2	C35—C34—H34A	120.6
C8—C9—H9B	108.2	C34—C35—C36	120.6 (3)
S2—C9—H9B	108.2	C34—C35—H35A	119.7
H9A—C9—H9B	107.3	C36—C35—H35A	119.7
C12—C11—C16	117.5 (3)	C31—C36—C35	121.4 (3)
C12—C11—Sn1	120.0 (3)	C31—C36—H36A	119.3
C16—C11—Sn1	122.4 (3)	C35—C36—H36A	119.3

Experimental details

Crystal data
Chemical formula	[Sn(C₆H₅)₃(C₉H₁₁O₂S₂)]
M_r	565.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.170 (4), 14.250 (7), 21.171 (9)
β (°)	95.871 (9)
V (Å³)	2452 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.23
Crystal size (mm)	0.34 × 0.32 × 0.29

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.661, 0.703
No. of measured, independent and observed [I > 2σ(I)] reflections	12531, 4503, 3086
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.075, 1.00
No. of reflections	4503
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.27

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).

Selected geometric parameters (Å, º) top

Sn1—C1	2.113 (3)	Sn1—C31	2.129 (3)
Sn1—C11	2.128 (3)	Sn1—C21	2.144 (3)

C1—Sn1—C11	114.15 (13)	C1—Sn1—C21	105.21 (13)
C1—Sn1—C31	111.22 (13)	C11—Sn1—C21	110.69 (12)
C11—Sn1—C31	109.40 (13)	C31—Sn1—C21	105.80 (12)

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