The Sn atom in the title compound, [Sn(C6H5)2(C5H10NO2S2)2], is six-coordinate in a cis-C2SnS4 octahedral environment.
Supporting information
CCDC reference: 155849
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.048
- wR factor = 0.112
- Data-to-parameter ratio = 20.5
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level B:
REFLT_03
From the CIF: _diffrn_reflns_theta_max 29.52
From the CIF: _reflns_number_total 6443
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 7369
Completeness (_total/calc) 87.43%
Alert B: < 90% complete (theta max?)
Alert Level C:
PLAT_732 Alert C Angle Calc 68.29(3), Rep 68.30(10) .... 3.33 s.u-Ratio
S1 -SN1 -S2 1.555 1.555 1.555
PLAT_732 Alert C Angle Calc 158.38(3), Rep 158.40(10) .... 3.33 s.u-Ratio
S1 -SN1 -S3 1.555 1.555 1.555
PLAT_732 Alert C Angle Calc 100.99(3), Rep 101.00(10) .... 3.33 s.u-Ratio
S1 -SN1 -S4 1.555 1.555 1.555
PLAT_732 Alert C Angle Calc 91.83(3), Rep 91.80(10) .... 3.33 s.u-Ratio
S2 -SN1 -S3 1.555 1.555 1.555
PLAT_732 Alert C Angle Calc 82.08(3), Rep 82.10(10) .... 3.33 s.u-Ratio
S2 -SN1 -S4 1.555 1.555 1.555
PLAT_732 Alert C Angle Calc 66.58(3), Rep 66.60(10) .... 3.33 s.u-Ratio
S3 -SN1 -S4 1.555 1.555 1.555
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
6 Alert Level C = Please check
A solution of carbon disulfide in methanol was added to a mixture of diphenyltin
dichloride and diethanolamine (1:2 molar ratio) at 277 K. The mixture was
stirred to afford a pale-yellow solid, which was collected and recrystallized
from a 3:2 methanol–chloroform mixture to afford (I) (m.p. 402–403 K).
Elemental analysis, found (calculated) for C22H30N2O4S4Sn: C 42.66
(41.72), H 4.60 (4.77), N 4.46 (4.42), Sn 18.30% (18.74%).
The hydroxyl H atoms were located and refined.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Bis[
N,
N-bis(2-hydroxyethyl)dithiocarbamato-
S,
S']diphenyltin(IV)
top
Crystal data top
[Sn(C6H5)2(C5H10NO2S2)2] | Z = 2 |
Mr = 633.41 | F(000) = 644 |
Triclinic, P1 | Dx = 1.596 Mg m−3 |
a = 9.0118 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.4051 (1) Å | Cell parameters from 7568 reflections |
c = 12.6024 (2) Å | θ = 1.6–29.5° |
α = 86.889 (1)° | µ = 1.32 mm−1 |
β = 69.575 (1)° | T = 298 K |
γ = 88.293 (1)° | Block, colorless |
V = 1318.24 (4) Å3 | 0.40 × 0.22 × 0.20 mm |
Data collection top
Siemens CCD area-detector diffractometer | 6443 independent reflections |
Radiation source: fine-focus sealed tube | 5242 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
Detector resolution: 8.33 pixels mm-1 | θmax = 29.5°, θmin = 1.6° |
ω scans | h = −12→10 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −17→16 |
Tmin = 0.621, Tmax = 0.779 | l = −17→12 |
9804 measured reflections | |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0278P)2] where P = (Fo2 + 2Fc2)/3 |
6443 reflections | (Δ/σ)max < 0.001 |
314 parameters | Δρmax = 2.31 e Å−3 |
0 restraints | Δρmin = −1.91 e Å−3 |
Crystal data top
[Sn(C6H5)2(C5H10NO2S2)2] | γ = 88.293 (1)° |
Mr = 633.41 | V = 1318.24 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.0118 (2) Å | Mo Kα radiation |
b = 12.4051 (1) Å | µ = 1.32 mm−1 |
c = 12.6024 (2) Å | T = 298 K |
α = 86.889 (1)° | 0.40 × 0.22 × 0.20 mm |
β = 69.575 (1)° | |
Data collection top
Siemens CCD area-detector diffractometer | 6443 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 5242 reflections with I > 2σ(I) |
Tmin = 0.621, Tmax = 0.779 | Rint = 0.053 |
9804 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | Δρmax = 2.31 e Å−3 |
6443 reflections | Δρmin = −1.91 e Å−3 |
314 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Sn1 | 0.29068 (3) | 0.19575 (2) | 0.31666 (2) | 0.0232 (1) | |
S1 | 0.4809 (1) | 0.31187 (8) | 0.14828 (8) | 0.0342 (2) | |
S2 | 0.4882 (1) | 0.30506 (9) | 0.37961 (8) | 0.0348 (2) | |
S3 | 0.1329 (1) | 0.13741 (8) | 0.52039 (8) | 0.0328 (2) | |
S4 | 0.0751 (1) | 0.35543 (8) | 0.43504 (8) | 0.0340 (2) | |
O1 | 0.8600 (5) | 0.6072 (3) | 0.2289 (4) | 0.066 (1) | |
O2 | 0.6820 (4) | 0.6105 (2) | 0.0990 (3) | 0.041 (1) | |
O3 | −0.1148 (4) | 0.2588 (3) | 0.8525 (3) | 0.046 (1) | |
O4 | −0.3642 (4) | 0.3716 (3) | 0.8287 (3) | 0.052 (1) | |
N1 | 0.7126 (3) | 0.3973 (2) | 0.2004 (3) | 0.026 (1) | |
N2 | −0.1236 (4) | 0.2547 (3) | 0.6212 (3) | 0.028 (1) | |
C1 | 0.1201 (4) | 0.1761 (3) | 0.2348 (3) | 0.024 (1) | |
C2 | −0.0250 (5) | 0.1264 (4) | 0.2925 (4) | 0.038 (1) | |
C3 | −0.1319 (5) | 0.1117 (4) | 0.2384 (4) | 0.048 (1) | |
C4 | −0.0985 (5) | 0.1455 (4) | 0.1273 (4) | 0.047 (1) | |
C5 | 0.0440 (5) | 0.1947 (4) | 0.0693 (4) | 0.044 (1) | |
C6 | 0.1515 (5) | 0.2103 (4) | 0.1226 (3) | 0.036 (1) | |
C7 | 0.4340 (4) | 0.0502 (3) | 0.2847 (3) | 0.029 (1) | |
C8 | 0.4524 (5) | −0.0167 (3) | 0.3716 (4) | 0.037 (1) | |
C9 | 0.5425 (6) | −0.1108 (4) | 0.3478 (5) | 0.051 (1) | |
C11 | 0.5973 (6) | −0.0738 (4) | 0.1504 (5) | 0.058 (1) | |
C10 | 0.6157 (6) | −0.1387 (4) | 0.2376 (6) | 0.060 (2) | |
C12 | 0.5071 (5) | 0.0192 (4) | 0.1745 (4) | 0.041 (1) | |
C13 | 0.5769 (4) | 0.3441 (3) | 0.2392 (3) | 0.026 (1) | |
C14 | 0.8028 (5) | 0.4161 (3) | 0.2750 (4) | 0.034 (1) | |
C15 | 0.7855 (6) | 0.5297 (4) | 0.3169 (4) | 0.050 (1) | |
C16 | 0.7893 (4) | 0.4265 (3) | 0.0796 (3) | 0.032 (1) | |
C17 | 0.7088 (5) | 0.5173 (3) | 0.0334 (3) | 0.035 (1) | |
C18 | 0.0136 (4) | 0.2521 (3) | 0.5340 (3) | 0.027 (1) | |
C19 | −0.1704 (4) | 0.1638 (3) | 0.7065 (3) | 0.033 (1) | |
C20 | −0.0864 (5) | 0.1626 (4) | 0.7921 (3) | 0.038 (1) | |
C21 | −0.2439 (5) | 0.3400 (4) | 0.6263 (4) | 0.043 (1) | |
C22 | −0.2737 (5) | 0.4166 (4) | 0.7200 (4) | 0.048 (1) | |
H1a | 0.812 (7) | 0.618 (5) | 0.189 (5) | 0.07 (2)* | |
H2a | 0.589 (6) | 0.621 (4) | 0.119 (4) | 0.05 (2)* | |
H3a | −0.044 (5) | 0.295 (4) | 0.830 (4) | 0.03 (1)* | |
H4a | −0.308 (6) | 0.332 (4) | 0.851 (4) | 0.04 (2)* | |
H2 | −0.0498 | 0.1030 | 0.3680 | 0.046* | |
H3 | −0.2278 | 0.0784 | 0.2779 | 0.058* | |
H4 | −0.1710 | 0.1353 | 0.0915 | 0.056* | |
H5 | 0.0679 | 0.2176 | −0.0063 | 0.053* | |
H6 | 0.2467 | 0.2443 | 0.0825 | 0.043* | |
H8 | 0.4037 | 0.0019 | 0.4464 | 0.045* | |
H9 | 0.5533 | −0.1551 | 0.4066 | 0.061* | |
H10 | 0.6776 | −0.2012 | 0.2217 | 0.072* | |
H11 | 0.6457 | −0.0928 | 0.0757 | 0.069* | |
H12 | 0.4950 | 0.0623 | 0.1152 | 0.050* | |
H14a | 0.9140 | 0.4014 | 0.2343 | 0.041* | |
H14b | 0.7681 | 0.3654 | 0.3400 | 0.041* | |
H15a | 0.6738 | 0.5478 | 0.3500 | 0.060* | |
H15b | 0.8315 | 0.5322 | 0.3757 | 0.060* | |
H16a | 0.7941 | 0.3629 | 0.0369 | 0.039* | |
H16b | 0.8974 | 0.4473 | 0.0667 | 0.039* | |
H17a | 0.7743 | 0.5366 | −0.0441 | 0.042* | |
H17b | 0.6082 | 0.4922 | 0.0327 | 0.042* | |
H19a | −0.1477 | 0.0965 | 0.6679 | 0.039* | |
H19b | −0.2838 | 0.1679 | 0.7466 | 0.039* | |
H20a | −0.1224 | 0.1013 | 0.8453 | 0.046* | |
H20b | 0.0265 | 0.1537 | 0.7529 | 0.046* | |
H21a | −0.3429 | 0.3057 | 0.6347 | 0.051* | |
H21b | −0.2107 | 0.3814 | 0.5545 | 0.051* | |
H22a | −0.1727 | 0.4397 | 0.7218 | 0.057* | |
H22b | −0.3287 | 0.4801 | 0.7034 | 0.057* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.0217 (1) | 0.0247 (1) | 0.0234 (1) | −0.0046 (1) | −0.0079 (1) | −0.0009 (1) |
S1 | 0.0340 (5) | 0.0418 (6) | 0.0326 (5) | −0.0181 (4) | −0.0187 (4) | 0.0070 (4) |
S2 | 0.0364 (5) | 0.0413 (6) | 0.0266 (5) | −0.0140 (4) | −0.0098 (4) | −0.0012 (4) |
S3 | 0.0317 (5) | 0.0336 (5) | 0.0270 (5) | 0.0034 (4) | −0.0038 (4) | 0.0032 (4) |
S4 | 0.0374 (5) | 0.0294 (5) | 0.0324 (5) | −0.0025 (4) | −0.0087 (4) | 0.0008 (4) |
O1 | 0.084 (3) | 0.044 (2) | 0.096 (3) | −0.026 (2) | −0.065 (3) | 0.010 (2) |
O2 | 0.038 (2) | 0.036 (2) | 0.049 (2) | −0.002 (1) | −0.017 (2) | −0.002 (1) |
O3 | 0.044 (2) | 0.060 (2) | 0.037 (2) | −0.005 (2) | −0.015 (2) | −0.012 (2) |
O4 | 0.039 (2) | 0.063 (2) | 0.042 (2) | 0.013 (2) | −0.002 (2) | −0.010 (2) |
N1 | 0.024 (1) | 0.029 (2) | 0.028 (2) | −0.006 (1) | −0.013 (1) | 0.002 (1) |
N2 | 0.025 (1) | 0.034 (2) | 0.025 (2) | 0.000 (1) | −0.008 (1) | −0.002 (1) |
C1 | 0.022 (2) | 0.023 (2) | 0.033 (2) | −0.001 (1) | −0.015 (1) | −0.003 (1) |
C2 | 0.034 (2) | 0.042 (2) | 0.041 (2) | −0.009 (2) | −0.017 (2) | 0.006 (2) |
C3 | 0.028 (2) | 0.057 (3) | 0.064 (3) | −0.015 (2) | −0.020 (2) | 0.002 (2) |
C4 | 0.032 (2) | 0.058 (3) | 0.061 (3) | −0.006 (2) | −0.028 (2) | −0.004 (2) |
C5 | 0.043 (2) | 0.060 (3) | 0.035 (2) | −0.004 (2) | −0.022 (2) | 0.000 (2) |
C6 | 0.027 (2) | 0.048 (2) | 0.033 (2) | −0.007 (2) | −0.011 (2) | 0.002 (2) |
C7 | 0.023 (2) | 0.030 (2) | 0.036 (2) | −0.003 (1) | −0.012 (2) | −0.006 (2) |
C8 | 0.035 (2) | 0.039 (2) | 0.047 (2) | −0.001 (2) | −0.026 (2) | −0.004 (2) |
C9 | 0.051 (3) | 0.036 (2) | 0.082 (4) | 0.003 (2) | −0.044 (3) | −0.001 (2) |
C10 | 0.042 (3) | 0.040 (3) | 0.106 (5) | 0.012 (2) | −0.031 (3) | −0.025 (3) |
C11 | 0.046 (3) | 0.055 (3) | 0.066 (3) | 0.007 (2) | −0.009 (3) | −0.029 (3) |
C12 | 0.039 (2) | 0.041 (2) | 0.042 (2) | 0.000 (2) | −0.011 (2) | −0.005 (2) |
C13 | 0.024 (2) | 0.023 (2) | 0.031 (2) | −0.003 (1) | −0.010 (1) | −0.001 (1) |
C14 | 0.032 (2) | 0.037 (2) | 0.041 (2) | −0.010 (2) | −0.022 (2) | 0.004 (2) |
C15 | 0.056 (3) | 0.048 (3) | 0.058 (3) | −0.009 (2) | −0.032 (2) | −0.016 (2) |
C16 | 0.025 (2) | 0.038 (2) | 0.030 (2) | −0.006 (2) | −0.004 (2) | −0.001 (2) |
C17 | 0.036 (2) | 0.038 (2) | 0.032 (2) | −0.011 (2) | −0.014 (2) | 0.004 (2) |
C18 | 0.027 (2) | 0.029 (2) | 0.024 (2) | −0.004 (1) | −0.009 (1) | −0.004 (1) |
C19 | 0.026 (2) | 0.038 (2) | 0.031 (2) | −0.010 (2) | −0.005 (2) | −0.001 (2) |
C20 | 0.039 (2) | 0.045 (2) | 0.030 (2) | −0.005 (2) | −0.011 (2) | 0.002 (2) |
C21 | 0.030 (2) | 0.054 (3) | 0.041 (2) | 0.02 (2) | −0.008 (2) | 0.000 (2) |
C22 | 0.039 (2) | 0.040 (2) | 0.052 (3) | 0.005 (2) | −0.001 (2) | −0.004 (2) |
Geometric parameters (Å, º) top
Sn1—C1 | 2.156 (4) | C16—C17 | 1.521 (6) |
Sn1—C7 | 2.160 (4) | C19—C20 | 1.517 (6) |
Sn1—S1 | 2.606 (1) | C21—C22 | 1.502 (7) |
Sn1—S2 | 2.624 (1) | O1—H1a | 0.77 (6) |
Sn1—S3 | 2.540 (1) | O2—H2a | 0.80 (5) |
Sn1—S4 | 2.827 (1) | O3—H3a | 0.76 (4) |
S1—C13 | 1.727 (4) | O4—H4a | 0.80 (5) |
S2—C13 | 1.717 (4) | C2—H2 | 0.9300 |
S3—C18 | 1.737 (4) | C3—H3 | 0.9300 |
S4—C18 | 1.700 (4) | C4—H4 | 0.9300 |
O1—C15 | 1.417 (6) | C5—H5 | 0.9300 |
O2—C17 | 1.423 (5) | C6—H6 | 0.9300 |
O3—C20 | 1.419 (5) | C8—H8 | 0.9300 |
O4—C22 | 1.420 (5) | C9—H9 | 0.9300 |
N1—C13 | 1.329 (4) | C10—H10 | 0.9300 |
N1—C16 | 1.465 (5) | C11—H11 | 0.9300 |
N1—C14 | 1.473 (5) | C12—H12 | 0.9300 |
N2—C18 | 1.339 (4) | C14—H14a | 0.9700 |
N2—C19 | 1.478 (5) | C14—H14b | 0.9700 |
N2—C21 | 1.479 (5) | C15—H15a | 0.9700 |
C1—C6 | 1.386 (5) | C15—H15b | 0.9700 |
C1—C2 | 1.398 (5) | C16—H16a | 0.9700 |
C2—C3 | 1.382 (6) | C16—H16b | 0.9700 |
C3—C4 | 1.369 (7) | C17—H17a | 0.9700 |
C4—C5 | 1.378 (6) | C17—H17b | 0.9700 |
C5—C6 | 1.381 (6) | C19—H19a | 0.9700 |
C7—C12 | 1.384 (6) | C19—H19b | 0.9700 |
C7—C8 | 1.391 (6) | C20—H20a | 0.9700 |
C8—C9 | 1.388 (6) | C20—H20b | 0.9700 |
C9—C10 | 1.372 (8) | C21—H21a | 0.9700 |
C10—C11 | 1.381 (8) | C21—H21b | 0.9700 |
C11—C12 | 1.376 (7) | C22—H22a | 0.9700 |
C14—C15 | 1.516 (6) | C22—H22b | 0.9700 |
| | | |
C1—Sn1—C7 | 104.9 (1) | C1—C2—H2 | 119.7 |
C1—Sn1—S1 | 94.2 (1) | C4—C3—H3 | 119.5 |
C1—Sn1—S2 | 154.8 (1) | C2—C3—H3 | 119.5 |
C1—Sn1—S3 | 101.6 (1) | C3—C4—H4 | 120.4 |
C1—Sn1—S4 | 83.8 (1) | C5—C4—H4 | 120.4 |
C7—Sn1—S1 | 96.0 (1) | C4—C5—H5 | 119.8 |
C7—Sn1—S2 | 95.2 (1) | C6—C5—H5 | 119.8 |
C7—Sn1—S3 | 94.1 (1) | C5—C6—H6 | 119.4 |
C7—Sn1—S4 | 160.3 (1) | C1—C6—H6 | 119.4 |
S1—Sn1—S2 | 68.3 (1) | C7—C8—H8 | 119.6 |
S1—Sn1—S3 | 158.4 (1) | C9—C8—H8 | 119.6 |
S1—Sn1—S4 | 101.0 (1) | C10—C9—H9 | 119.9 |
S2—Sn1—S3 | 91.8 (1) | C8—C9—H9 | 119.9 |
S2—Sn1—S4 | 82.1 (1) | C11—C10—H10 | 120.1 |
S3—Sn1—S4 | 66.6 (1) | C9—C10—H10 | 120.1 |
C13—S1—Sn1 | 87.1 (1) | C10—C11—H11 | 120.1 |
C13—S2—Sn1 | 86.8 (1) | C12—C11—H11 | 120.1 |
C18—S3—Sn1 | 90.6 (1) | C11—C12—H12 | 119.2 |
C18—S4—Sn1 | 82.1 (1) | C7—C12—H12 | 119.2 |
C13—N1—C16 | 121.7 (3) | N1—C14—H14a | 108.8 |
C13—N1—C14 | 120.9 (3) | C15—C14—H14a | 108.8 |
C16—N1—C14 | 116.9 (3) | N1—C14—H14b | 108.8 |
C18—N2—C19 | 121.0 (3) | C15—C14—H14b | 108.8 |
C18—N2—C21 | 121.1 (3) | H14a—C14—H14b | 107.6 |
C19—N2—C21 | 117.3 (3) | O1—C15—H15a | 109.1 |
C6—C1—C2 | 117.7 (4) | C14—C15—H15a | 109.1 |
C6—C1—Sn1 | 121.3 (3) | O1—C15—H15b | 109.1 |
C2—C1—Sn1 | 121.0 (3) | C14—C15—H15b | 109.1 |
C3—C2—C1 | 120.5 (4) | H15a—C15—H15b | 107.9 |
C4—C3—C2 | 120.9 (4) | N1—C16—H16a | 108.5 |
C3—C4—C5 | 119.2 (4) | C17—C16—H16a | 108.5 |
C4—C5—C6 | 120.4 (4) | N1—C16—H16b | 108.5 |
C5—C6—C1 | 121.2 (4) | C17—C16—H16b | 108.5 |
C12—C7—C8 | 117.9 (4) | H16a—C16—H16b | 107.5 |
C12—C7—Sn1 | 119.7 (3) | O2—C17—H17a | 109.2 |
C8—C7—Sn1 | 122.4 (3) | C16—C17—H17a | 109.2 |
C7—C8—C9 | 120.7 (4) | O2—C17—H17a | 109.2 |
C10—C9—C8 | 120.2 (5) | C16—C17—H17b | 109.2 |
C11—C10—C9 | 119.8 (4) | H17a—C17—H17b | 107.9 |
C10—C11—C12 | 119.8 (5) | N2—C19—H19a | 108.9 |
C11—C12—C7 | 121.6 (4) | C20—C19—H19a | 108.9 |
N1—C13—S2 | 122.5 (3) | N2—C19—H19b | 108.9 |
N1—C13—S1 | 120.5 (3) | C20—C19—H19b | 108.9 |
S2—C13—S1 | 116.9 (2) | H19a—C19—H19b | 107.7 |
N1—C14—C15 | 114.0 (3) | O3—C20—H20a | 109.2 |
O1—C15—C14 | 112.3 (4) | C19—C20—H20a | 109.2 |
N1—C16—C17 | 115.2 (3) | O3—C20—H20b | 109.2 |
O2—C17—C16 | 112.2 (3) | C19—C20—H20b | 109.2 |
N2—C18—S4 | 122.9 (3) | H20a—C20—H20b | 107.9 |
N2—C18—S3 | 118.5 (3) | N2—C21—H21a | 108.4 |
S4—C18—S3 | 118.6 (2) | C22—C21—H21a | 108.4 |
N2—C19—C20 | 113.4 (3) | N2—C21—H21b | 108.4 |
O3—C20—C19 | 112.2 (3) | C22—C21—H21b | 108.4 |
N2—C21—C22 | 115.4 (4) | H21a—C21—H21b | 107.5 |
O4—C22—C21 | 113.7 (4) | O4—C22—H22a | 108.8 |
C15—O1—H1a | 111 (5) | C21—C22—H22a | 108.8 |
C17—O2—H2a | 105 (4) | O4—C22—H22b | 108.8 |
C20—O3—H3a | 111 (3) | C21—C22—H22b | 108.8 |
C22—O4—H4a | 109 (3) | H22a—C22—H22b | 107.7 |
C3—C2—H2 | 119.7 | | |
| | | |
C1—Sn1—S1—C13 | 167.0 (2) | S4—Sn1—C7—C12 | 168.9 (2) |
C7—Sn1—S1—C13 | −87.6 (2) | C1—Sn1—C7—C8 | −123.4 (3) |
S3—Sn1—S1—C13 | 29.9 (2) | S3—Sn1—C7—C8 | −20.2 (3) |
S2—Sn1—S1—C13 | 5.6 (1) | S1—Sn1—C7—C8 | 140.6 (3) |
S4—Sn1—S1—C13 | 82.4 (1) | S2—Sn1—C7—C8 | 72.0 (3) |
C1—Sn1—S2—C13 | −54.2 (3) | S4—Sn1—C7—C8 | −9.0 (5) |
C7—Sn1—S2—C13 | 88.8 (2) | C12—C7—C8—C9 | 0.6 (6) |
S3—Sn1—S2—C13 | −177.0 (1) | Sn1—C7—C8—C9 | 178.5 (3) |
S1—Sn1—S2—C13 | −5.7 (1) | C7—C8—C9—C10 | 0.4 (7) |
S4—Sn1—S2—C13 | −110.9 (1) | C8—C9—C10—C11 | −1.1 (8) |
C1—Sn1—S3—C18 | −69.4 (2) | C9—C10—C11—C12 | 0.8 (8) |
C7—Sn1—S3—C18 | −175.5 (2) | C10—C11—C12—C7 | 0.3 (8) |
S1—Sn1—S3—C18 | 66.7 (2) | C8—C7—C12—C11 | −0.9 (6) |
S2—Sn1—S3—C18 | 89.2 (1) | Sn1—C7—C12—C11 | −178.9 (4) |
S4—Sn1—S3—C18 | 8.6 (1) | C16—N1—C13—S2 | 177.8 (3) |
C1—Sn1—S4—C18 | 96.7 (2) | C14—N1—C13—S2 | 6.2 (5) |
C7—Sn1—S4—C18 | −21.0 (3) | C16—N1—C13—S1 | −2.6 (5) |
S3—Sn1—S4—C18 | −8.9 (1) | C14—N1—C13—S1 | −174.2 (3) |
S1—Sn1—S4—C18 | −170.3 (1) | Sn1—S2—C13—N1 | −171.5 (3) |
S2—Sn1—S4—C18 | −104.3 (1) | Sn1—S2—C13—S1 | 8.9 (2) |
C7—Sn1—C1—C6 | −89.5 (3) | Sn1—S1—C13—N1 | 171.4 (3) |
S3—Sn1—C1—C6 | 173.0 (3) | Sn1—S1—C13—S2 | −9.0 (2) |
S1—Sn1—C1—C6 | 7.9 (3) | C13—N1—C14—C15 | −102.5 (4) |
S2—Sn1—C1—C6 | 52.2 (4) | C16—N1—C14—C15 | 85.6 (4) |
S4—Sn1—C1—C6 | 108.5 (3) | N1—C14—C15—O1 | −69.2 (5) |
C7—Sn1—C1—C2 | 89.3 (3) | C13—N1—C16—C17 | 72.8 (5) |
S3—Sn1—C1—C2 | −8.2 (3) | C14—N1—C16—C17 | −115.4 (4) |
S1—Sn1—C1—C2 | −173.4 (3) | N1—C16—C17—O2 | 52.2 (5) |
S2—Sn1—C1—C2 | −129.1 (3) | C19—N2—C18—S4 | −178.6 (3) |
S4—Sn1—C1—C2 | −72.7 (3) | C21—N2—C18—S4 | 10.6 (5) |
C6—C1—C2—C3 | 0.4 (6) | C19—N2—C18—S3 | 2.2 (5) |
Sn1—C1—C2—C3 | −178.3 (3) | C21—N2—C18—S3 | −168.5 (3) |
C1—C2—C3—C4 | −0.1 (7) | Sn1—S4—C18—N2 | −165.5 (3) |
C2—C3—C4—C5 | 0.0 (8) | Sn1—S4—C18—S3 | 13.6 (2) |
C3—C4—C5—C6 | −0.3 (8) | Sn1—S3—C18—N2 | 164.1 (3) |
C4—C5—C6—C1 | 0.7 (7) | Sn1—S3—C18—S4 | −15.0 (2) |
C2—C1—C6—C5 | −0.7 (6) | C18—N2—C19—C20 | 77.7 (5) |
Sn1—C1—C6—C5 | 178.1 (3) | C21—N2—C19—C20 | −111.2 (4) |
C1—Sn1—C7—C12 | 54.5 (3) | N2—C19—C20—O3 | 58.8 (4) |
S3—Sn1—C7—C12 | 157.7 (3) | C18—N2—C21—C22 | −113.7 (4) |
S1—Sn1—C7—C12 | −41.4 (3) | C19—N2—C21—C22 | 75.2 (5) |
S2—Sn1—C7—C12 | −110.1 (3) | N2—C21—C22—O4 | −75.1 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1a···O2 | 0.77 (6) | 1.90 (6) | 2.660 (5) | 167 (7) |
O2—H2a···O4i | 0.80 (5) | 1.90 (5) | 2.692 (5) | 173 (5) |
O3—H3a···O1ii | 0.76 (4) | 1.98 (5) | 2.736 (5) | 179 (4) |
O4—H4a···O3 | 0.80 (5) | 1.95 (5) | 2.710 (5) | 159 (5) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data |
Chemical formula | [Sn(C6H5)2(C5H10NO2S2)2] |
Mr | 633.41 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 9.0118 (2), 12.4051 (1), 12.6024 (2) |
α, β, γ (°) | 86.889 (1), 69.575 (1), 88.293 (1) |
V (Å3) | 1318.24 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.32 |
Crystal size (mm) | 0.40 × 0.22 × 0.20 |
|
Data collection |
Diffractometer | Siemens CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.621, 0.779 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9804, 6443, 5242 |
Rint | 0.053 |
(sin θ/λ)max (Å−1) | 0.693 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.112, 0.98 |
No. of reflections | 6443 |
No. of parameters | 314 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 2.31, −1.91 |
Selected geometric parameters (Å, º) topSn1—C1 | 2.156 (4) | Sn1—S2 | 2.624 (1) |
Sn1—C7 | 2.160 (4) | Sn1—S3 | 2.540 (1) |
Sn1—S1 | 2.606 (1) | Sn1—S4 | 2.827 (1) |
| | | |
C1—Sn1—C7 | 104.9 (1) | C7—Sn1—S4 | 160.3 (1) |
C1—Sn1—S1 | 94.2 (1) | S1—Sn1—S2 | 68.3 (1) |
C1—Sn1—S2 | 154.8 (1) | S1—Sn1—S3 | 158.4 (1) |
C1—Sn1—S3 | 101.6 (1) | S1—Sn1—S4 | 101.0 (1) |
C1—Sn1—S4 | 83.8 (1) | S2—Sn1—S3 | 91.8 (1) |
C7—Sn1—S1 | 96.0 (1) | S2—Sn1—S4 | 82.1 (1) |
C7—Sn1—S2 | 95.2 (1) | S3—Sn1—S4 | 66.6 (1) |
C7—Sn1—S3 | 94.1 (1) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1a···O2 | 0.77 (6) | 1.90 (6) | 2.660 (5) | 167 (7) |
O2—H2a···O4i | 0.80 (5) | 1.90 (5) | 2.692 (5) | 173 (5) |
O3—H3a···O1ii | 0.76 (4) | 1.98 (5) | 2.736 (5) | 179 (4) |
O4—H4a···O3 | 0.80 (5) | 1.95 (5) | 2.710 (5) | 159 (5) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1. |
Six-coordinate bis-chelated diaryltin compounds generally adopt a cis-octahedral geometry (Ng et al., 1987). In diphenyltin bis(diethyldithiocarbamate), the chelation by one dithiocarbamate group is relatively symmetrical [Sn—S = 2.613 (5) and 2.637 (5) Å] whereas the chelation by the other is not [Sn—S = 2.548 (5) and 2.790 (6) Å]; the C—Sn—C angle is opened up to 101.4 (6) Å (Lindley & Carr, 1974). The bond dimensions in the title compound, (I), are similar to those found in diphenyltin bis(diethyldithiocarbamate); in the title compound, the hydroxyl group of each dithiocarbamate ligand is hydrogen bonded to the hydroxyl group of the same dithiocarbamate group. Adjacent molecules are linked by hydrogen bonds into a linear chain structure. The cis geometry contrasts with the skew-trapezoidal geometry [C—Sn—C = 139.3 (2)°] adopted by the dimethyltin homolog (Yang Farina et al., 2000).