Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703961X/hy2075sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680703961X/hy2075Isup2.hkl |
CCDC reference: 651149
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%).
H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å (CH), 0.97 Å (CH2) and Uiso = 1.2Ueq(C), and with C—H = 0.96 Å (CH3) and Uiso = 1.5Ueq(C).
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).
For related literature, see: Marcel (2002); Zhu et al. (2003)
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).
[Sn(C6H5)3(C9H11O2S2)] | F(000) = 1144 |
Mr = 565.29 | Dx = 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 |
Bruker SMART APEX CCD area-detector diffractometer | 4503 independent reflections |
Radiation source: fine-focus sealed tube | 3086 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 25.4°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.661, Tmax = 0.703 | k = −15→17 |
12531 measured reflections | l = −20→25 |
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(Fo2) + (0.0317P)2 + 0.6236P] where P = (Fo2 + 2Fc2)/3 |
4503 reflections | (Δ/σ)max = 0.001 |
289 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
[Sn(C6H5)3(C9H11O2S2)] | V = 2452 (2) Å3 |
Mr = 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)° |
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 = 0.703 | Rint = 0.033 |
12531 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.37 e Å−3 |
4503 reflections | Δρmin = −0.27 e Å−3 |
289 parameters |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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)] |
Mr | 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) |
Tmin, Tmax | 0.661, 0.703 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12531, 4503, 3086 |
Rint | 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 |
Δρmax, Δρmin (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).
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) |
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).