Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800020316/na6027sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536800020316/na6027Isup2.hkl |
CCDC reference: 155847
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.009 Å
- R factor = 0.054
- wR factor = 0.146
- Data-to-parameter ratio = 23.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_320 Alert C Check Hybridisation of C(15) in main residue ? PLAT_360 Alert C Short C(sp3)-C(sp3) Bond C(15) - C(16) = 1.41 Ang. PLAT_601 Alert C Structure contains solvent accessible VOIDS of 32.00 A 3 PLAT_732 Alert C Angle Calc 67.80(4), Rep 67.80(10) .... 2.50 s.u-Ratio S3 -SN1 -S4 1.555 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
4 Alert Level C = Please check
A solution of carbon disulfide in methanol was added to a mixture of diphenyltin dichloride and 2-hydroxyethylmethylamine (1:2 molar stoichiometry) at 277 K. The mixture was stirred to afford a pale-yellow solid, which was collected and recrystallized from a methanol/chloroform mixture to afford the title compound (m.p. 401–402 K). Elemental analysis, found (calculated) for C20H26N2O2S4Sn: C 40.40 (41.90), H 4.83 (4.57), N 5.24 (4.89), Sn 20.88% (20.70%).
One of the two hydroxyethyl groups is disordered. The N—C distance was DFIXed at 1.47±0.01 Å, the C—C distance at 1.54±0.01 Å and the C—O distance at 1.43±0.01 Å; the S1/S2/C13/N1/C14/C15 system was restrained to be planar by FLAT 0.01.
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.
Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound at the 50% probability level. H atoms are shown as circles of arbitrary radii. |
[Sn(C6H5)2(C4H8NOS2)] | F(000) = 1160 |
Mr = 573.36 | Dx = 1.532 Mg m−3 |
Monoclinic, P2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9931 (1) Å | Cell parameters from 8192 reflections |
b = 12.2068 (1) Å | θ = 1.7–28.3° |
c = 22.6703 (3) Å | µ = 1.38 mm−1 |
β = 92.507 (1)° | T = 298 K |
V = 2486.29 (5) Å3 | Block, colorless |
Z = 4 | 0.26 × 0.22 × 0.16 mm |
Siemens CCD area-detector diffractometer | 6025 independent reflections |
Radiation source: fine-focus sealed tube | 4060 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.087 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 1.7° |
ω scans | h = −11→11 |
Absorption correction: empirical (SADABS; Sheldrick, 1996) | k = −11→16 |
Tmin = 0.715, Tmax = 0.809 | l = −30→22 |
17084 measured reflections |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | Riding |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0636P)2] where P = (Fo2 + 2Fc2)/3 |
6025 reflections | (Δ/σ)max = 0.001 |
262 parameters | Δρmax = 1.22 e Å−3 |
6 restraints | Δρmin = −1.77 e Å−3 |
[Sn(C6H5)2(C4H8NOS2)] | V = 2486.29 (5) Å3 |
Mr = 573.36 | Z = 4 |
Monoclinic, P2/c | Mo Kα radiation |
a = 8.9931 (1) Å | µ = 1.38 mm−1 |
b = 12.2068 (1) Å | T = 298 K |
c = 22.6703 (3) Å | 0.26 × 0.22 × 0.16 mm |
β = 92.507 (1)° |
Siemens CCD area-detector diffractometer | 6025 independent reflections |
Absorption correction: empirical (SADABS; Sheldrick, 1996) | 4060 reflections with I > 2σ(I) |
Tmin = 0.715, Tmax = 0.809 | Rint = 0.087 |
17084 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 6 restraints |
wR(F2) = 0.146 | Riding |
S = 0.98 | Δρmax = 1.22 e Å−3 |
6025 reflections | Δρmin = −1.77 e Å−3 |
262 parameters |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.17456 (4) | 0.78194 (3) | 0.42776 (2) | 0.0349 (1) | |
S1 | 0.2827 (2) | 0.6240 (1) | 0.36459 (7) | 0.0484 (4) | |
S2 | 0.4278 (2) | 0.7060 (1) | 0.47491 (7) | 0.0483 (4) | |
S3 | 0.1238 (2) | 0.8751 (1) | 0.52551 (6) | 0.0494 (4) | |
S4 | 0.0492 (2) | 0.6414 (1) | 0.50616 (7) | 0.0481 (4) | |
N1 | 0.5553 (5) | 0.5669 (3) | 0.4037 (2) | 0.060 (1) | |
N2 | −0.0205 (6) | 0.7524 (4) | 0.6013 (2) | 0.051 (1) | |
O1 | 0.6106 (6) | 0.3501 (5) | 0.2909 (3) | 0.095 (2) | |
O2 | 0.1249 (7) | 0.7528 (5) | 0.7169 (2) | 0.101 (2) | |
C1 | −0.0402 (5) | 0.7854 (4) | 0.3808 (2) | 0.038 (1) | |
C2 | −0.1537 (6) | 0.8506 (5) | 0.4017 (3) | 0.057 (2) | |
C3 | −0.2905 (7) | 0.8563 (6) | 0.3722 (4) | 0.068 (2) | |
C4 | −0.3172 (7) | 0.7974 (6) | 0.3210 (3) | 0.064 (2) | |
C5 | −0.2080 (8) | 0.7349 (6) | 0.2990 (3) | 0.065 (2) | |
C6 | −0.0682 (6) | 0.7273 (5) | 0.3290 (3) | 0.053 (2) | |
C7 | 0.2874 (5) | 0.9229 (4) | 0.3915 (2) | 0.040 (1) | |
C8 | 0.2880 (6) | 0.9347 (5) | 0.3311 (3) | 0.046 (1) | |
C9 | 0.3585 (7) | 1.0229 (5) | 0.3058 (3) | 0.060 (2) | |
C10 | 0.4252 (7) | 1.1009 (5) | 0.3411 (4) | 0.065 (2) | |
C11 | 0.4238 (8) | 1.0912 (6) | 0.4018 (3) | 0.068 (2) | |
C12 | 0.3569 (7) | 1.0027 (5) | 0.4268 (3) | 0.054 (2) | |
C13 | 0.4346 (5) | 0.6266 (3) | 0.4131 (2) | 0.042 (1) | |
C14 | 0.6864 (6) | 0.5692 (5) | 0.4442 (3) | 0.069 (2) | |
C15 | 0.5698 (9) | 0.4996 (5) | 0.3503 (3) | 0.134 (5) | |
C16 | 0.579 (1) | 0.3842 (7) | 0.3486 (4) | 0.158 (6) | |
C17 | 0.0435 (6) | 0.7545 (4) | 0.5495 (2) | 0.041 (1) | |
C18 | −0.0934 (9) | 0.6534 (7) | 0.6232 (4) | 0.094 (3) | |
C19 | −0.0220 (7) | 0.8491 (6) | 0.6391 (3) | 0.062 (2) | |
C20 | 0.1133 (8) | 0.8515 (7) | 0.6796 (3) | 0.076 (2) | |
H1a | 0.7030 | 0.3819 | 0.2799 | 0.142* | |
H2a | 0.2130 | 0.7572 | 0.7422 | 0.151* | |
H2 | −0.1368 | 0.8909 | 0.4361 | 0.068* | |
H3 | −0.3651 | 0.9001 | 0.3868 | 0.082* | |
H4 | −0.4103 | 0.8005 | 0.3016 | 0.077* | |
H5 | −0.2257 | 0.6967 | 0.2639 | 0.078* | |
H6 | 0.0057 | 0.6833 | 0.3140 | 0.063* | |
H8 | 0.2405 | 0.8828 | 0.3069 | 0.055* | |
H9 | 0.3603 | 1.0290 | 0.2650 | 0.072* | |
H10 | 0.4715 | 1.1607 | 0.3242 | 0.078* | |
H11 | 0.4684 | 1.1448 | 0.4258 | 0.082* | |
H12 | 0.3580 | 0.9960 | 0.4676 | 0.065* | |
H14a | 0.7649 | 0.5272 | 0.4278 | 0.104* | |
H14b | 0.6617 | 0.5383 | 0.4815 | 0.104* | |
H14c | 0.7187 | 0.6435 | 0.4499 | 0.104* | |
H15a | 0.4860 | 0.5191 | 0.3240 | 0.161* | |
H15b | 0.6580 | 0.5262 | 0.3318 | 0.161* | |
H16a | 0.4854 | 0.3526 | 0.3598 | 0.190* | |
H16b | 0.6567 | 0.3591 | 0.3763 | 0.190* | |
H18a | −0.1325 | 0.6682 | 0.6611 | 0.140* | |
H18b | −0.0222 | 0.5950 | 0.6267 | 0.140* | |
H18c | −0.1732 | 0.6325 | 0.5959 | 0.140* | |
H19a | −0.1104 | 0.8481 | 0.6622 | 0.074* | |
H19b | −0.0251 | 0.9146 | 0.6149 | 0.074* | |
H20a | 0.2011 | 0.8572 | 0.6564 | 0.091* | |
H20b | 0.1098 | 0.9158 | 0.7047 | 0.091* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0321 (2) | 0.0368 (2) | 0.0354 (2) | 0.0027 (1) | −0.0016 (1) | −0.0037 (2) |
S1 | 0.0383 (7) | 0.0530 (8) | 0.0525 (8) | 0.0132 (6) | −0.0146 (6) | −0.0164 (7) |
S2 | 0.0432 (8) | 0.0571 (9) | 0.0435 (8) | 0.0086 (6) | −0.0120 (6) | −0.0082 (7) |
S3 | 0.070 (1) | 0.0382 (7) | 0.0408 (8) | −0.0021 (7) | 0.0120 (7) | −0.0056 (6) |
S4 | 0.0485 (8) | 0.0378 (7) | 0.0573 (9) | 0.0002 (6) | −0.0077 (7) | 0.0012 (7) |
N1 | 0.045 (3) | 0.063 (3) | 0.070 (4) | 0.023 (2) | −0.020 (3) | −0.022 (3) |
N2 | 0.047 (3) | 0.059 (3) | 0.048 (3) | 0.001 (2) | 0.010 (2) | 0.006 (2) |
O1 | 0.085 (4) | 0.110 (4) | 0.091 (4) | 0.006 (3) | 0.027 (3) | −0.048 (4) |
O2 | 0.084 (4) | 0.167 (6) | 0.051 (3) | 0.025 (4) | −0.003 (3) | 0.024 (4) |
C1 | 0.025 (2) | 0.046 (3) | 0.041 (3) | −0.001 (2) | −0.003 (2) | 0.008 (2) |
C2 | 0.043 (3) | 0.048 (3) | 0.078 (4) | 0.008 (3) | −0.009 (3) | −0.007 (3) |
C3 | 0.039 (3) | 0.066 (4) | 0.099 (6) | 0.020 (3) | 0.003 (4) | 0.015 (4) |
C4 | 0.037 (3) | 0.086 (5) | 0.068 (4) | 0.006 (3) | −0.009 (3) | 0.022 (4) |
C5 | 0.055 (4) | 0.096 (5) | 0.044 (3) | −0.004 (4) | −0.014 (3) | 0.004 (4) |
C6 | 0.032 (3) | 0.085 (4) | 0.040 (3) | 0.005 (3) | −0.004 (2) | −0.003 (3) |
C7 | 0.031 (3) | 0.044 (3) | 0.044 (3) | 0.002 (2) | 0.004 (2) | −0.004 (2) |
C8 | 0.040 (3) | 0.049 (3) | 0.047 (3) | −0.001 (2) | 0.005 (3) | −0.006 (3) |
C9 | 0.048 (3) | 0.076 (4) | 0.056 (4) | 0.009 (3) | 0.016 (3) | 0.006 (3) |
C10 | 0.052 (4) | 0.051 (4) | 0.093 (6) | −0.008 (3) | 0.014 (4) | 0.010 (4) |
C11 | 0.061 (4) | 0.059 (4) | 0.084 (5) | −0.018 (3) | −0.005 (4) | −0.006 (4) |
C12 | 0.050 (3) | 0.059 (4) | 0.053 (4) | −0.006 (3) | −0.003 (3) | −0.003 (3) |
C13 | 0.036 (3) | 0.040 (3) | 0.048 (3) | 0.003 (2) | −0.002 (2) | −0.003 (2) |
C14 | 0.043 (3) | 0.074 (4) | 0.089 (5) | 0.022 (3) | −0.025 (4) | −0.008 (4) |
C15 | 0.086 (7) | 0.134 (9) | 0.18 (1) | 0.053 (6) | −0.068 (7) | −0.057 (9) |
C16 | 0.13 (1) | 0.118 (9) | 0.23 (2) | −0.040 (8) | −0.03 (1) | 0.06 (1) |
C17 | 0.035 (3) | 0.048 (3) | 0.041 (3) | 0.007 (2) | −0.001 (2) | 0.005 (2) |
C18 | 0.087 (6) | 0.100 (6) | 0.097 (6) | −0.030 (5) | 0.036 (5) | 0.015 (5) |
C19 | 0.052 (4) | 0.091 (5) | 0.043 (3) | 0.022 (3) | 0.011 (3) | −0.003 (3) |
C20 | 0.073 (5) | 0.100 (6) | 0.056 (4) | 0.000 (4) | 0.015 (4) | −0.017 (4) |
Sn1—C1 | 2.164 (5) | C15—C16 | 1.411 (8) |
Sn1—C7 | 2.177 (5) | C19—C20 | 1.49 (1) |
Sn1—S1 | 2.614 (1) | O1—H1a | 0.9600 |
Sn1—S2 | 2.641 (1) | O2—H2a | 0.9600 |
Sn1—S3 | 2.550 (1) | C2—H2 | 0.9300 |
Sn1—S4 | 2.748 (2) | C3—H3 | 0.9300 |
S1—C13 | 1.717 (6) | C4—H4 | 0.9300 |
S2—C13 | 1.706 (6) | C5—H5 | 0.9300 |
S3—C17 | 1.737 (6) | C6—H6 | 0.9300 |
S4—C17 | 1.697 (6) | C8—H8 | 0.9300 |
N1—C13 | 1.332 (7) | C9—H9 | 0.9300 |
N1—C14 | 1.463 (8) | C10—H10 | 0.9300 |
N1—C15 | 1.474 (7) | C11—H11 | 0.9300 |
N2—C17 | 1.331 (7) | C12—H12 | 0.9300 |
N2—C19 | 1.459 (8) | C14—H14a | 0.9600 |
N2—C18 | 1.471 (8) | C14—H14b | 0.9600 |
O1—C16 | 1.412 (8) | C14—H14c | 0.9600 |
O2—C20 | 1.473 (9) | C15—H15a | 0.9700 |
C1—C6 | 1.386 (8) | C15—H15b | 0.9700 |
C1—C2 | 1.393 (7) | C16—H16a | 0.9700 |
C2—C3 | 1.376 (9) | C16—H16b | 0.9700 |
C3—C4 | 1.38 (1) | C18—H18a | 0.9600 |
C4—C5 | 1.356 (9) | C18—H18b | 0.9600 |
C5—C6 | 1.406 (8) | C18—H18c | 0.9600 |
C8—C9 | 1.386 (8) | C19—H19a | 0.9700 |
C9—C10 | 1.365 (9) | C19—H19b | 0.9700 |
C10—C11 | 1.38 (1) | C20—H20a | 0.9700 |
C11—C12 | 1.370 (9) | C20—H20b | 0.9700 |
C1—Sn1—C7 | 102.7 (2) | C3—C2—H2 | 119.4 |
C1—Sn1—S1 | 95.2 (1) | C1—C2—H2 | 119.4 |
C1—Sn1—S2 | 160.2 (1) | C2—C3—H3 | 119.9 |
C1—Sn1—S3 | 103.2 (1) | C4—C3—H3 | 119.9 |
C1—Sn1—S4 | 87.0 (1) | C5—C4—H4 | 119.9 |
C7—Sn1—S1 | 100.7 (1) | C3—C4—H4 | 119.9 |
C7—Sn1—S2 | 91.3 (1) | C4—C5—H5 | 119.8 |
C7—Sn1—S3 | 94.6 (1) | C6—C5—H5 | 119.8 |
C7—Sn1—S4 | 161.6 (2) | C1—C6—H6 | 119.9 |
S1—Sn1—S2 | 68.2 (1) | C5—C6—H6 | 119.9 |
S1—Sn1—S3 | 152.9 (1) | C7—C8—H8 | 119.6 |
S1—Sn1—S4 | 93.8 (1) | C9—C8—H8 | 119.6 |
S2—Sn1—S3 | 89.4 (1) | C10—C9—H9 | 120.1 |
S2—Sn1—S4 | 83.7 (1) | C8—C9—H9 | 120.1 |
S3—Sn1—S4 | 67.8 (1) | C9—C10—H10 | 120.0 |
C13—S1—Sn1 | 86.6 (2) | C11—C10—H10 | 120.0 |
C13—S2—Sn1 | 85.9 (2) | C12—C11—H11 | 119.9 |
C17—S3—Sn1 | 89.2 (2) | C10—C11—H11 | 119.9 |
C17—S4—Sn1 | 83.7 (2) | C11—C12—H12 | 119.7 |
C13—N1—C14 | 122.0 (5) | C7—C12—H12 | 119.7 |
C13—N1—C15 | 122.6 (6) | N1—C14—H14a | 109.5 |
C14—N1—C15 | 115.3 (5) | N1—C14—H14b | 109.5 |
C17—N2—C19 | 121.2 (5) | H14a—C14—H14b | 109.5 |
C17—N2—C18 | 122.0 (6) | N1—C14—H14c | 109.5 |
C19—N2—C18 | 116.8 (5) | H14a—C14—H14c | 109.5 |
C6—C1—C2 | 118.1 (5) | H14b—C14—H14c | 109.5 |
C6—C1—Sn1 | 122.1 (4) | C16—C15—H15a | 105.8 |
C2—C1—Sn1 | 119.7 (4) | N1—C15—H15a | 105.8 |
C3—C2—C1 | 121.2 (6) | C16—C15—H15b | 105.8 |
C2—C3—C4 | 120.1 (6) | N1—C15—H15b | 105.8 |
C5—C4—C3 | 120.1 (6) | H15a—C15—H15b | 106.2 |
C4—C5—C6 | 120.4 (6) | C15—C16—H16a | 109.8 |
C1—C6—C5 | 120.1 (6) | O1—C16—H16a | 109.8 |
C8—C7—C12 | 118.5 (5) | C15—C16—H16b | 109.8 |
C8—C7—Sn1 | 118.7 (4) | O1—C16—H16b | 109.8 |
C12—C7—Sn1 | 122.8 (4) | H16a—C16—H16b | 108.2 |
C7—C8—C9 | 120.9 (6) | N2—C18—H18a | 109.5 |
C10—C9—C8 | 119.9 (6) | N2—C18—H18b | 109.5 |
C9—C10—C11 | 120.0 (6) | H18a—C18—H18b | 109.5 |
C12—C11—C10 | 120.1 (6) | N2—C18—H18c | 109.5 |
C11—C12—C7 | 120.6 (6) | H18a—C18—H18c | 109.5 |
N1—C13—S2 | 120.1 (4) | H18b—C18—H18c | 109.5 |
N1—C13—S1 | 121.2 (4) | N2—C19—H19a | 109.6 |
S2—C13—S1 | 118.7 (3) | C20—C19—H19a | 109.6 |
C16—C15—N1 | 125.9 (6) | N2—C19—H19b | 109.6 |
C15—C16—O1 | 109.5 (8) | C20—C19—H19b | 109.6 |
N2—C17—S4 | 121.3 (4) | H19a—C19—H19b | 108.1 |
N2—C17—S3 | 119.6 (4) | O2—C20—H20a | 109.3 |
S4—C17—S3 | 119.0 (3) | C19—C20—H20a | 109.3 |
N2—C19—C20 | 110.5 (5) | O2—C20—H20b | 109.3 |
O2—C20—C19 | 111.8 (6) | C19—C20—H20b | 109.3 |
C16—O1—H1a | 109.5 | H20a—C20—H20b | 107.9 |
C20—O2—H2a | 109.5 | ||
C1—Sn1—S1—C13 | −173.8 (1) | S3—Sn1—C7—C8 | −154.3 (4) |
C7—Sn1—S1—C13 | 82.2 (2) | S1—Sn1—C7—C8 | 48.2 (4) |
S3—Sn1—S1—C13 | −40.9 (1) | S2—Sn1—C7—C8 | 116.2 (4) |
S2—Sn1—S1—C13 | −4.8 (1) | S4—Sn1—C7—C8 | −170.1 (3) |
S4—Sn1—S1—C13 | −86.5 (1) | C1—Sn1—C7—C12 | 129.2 (5) |
C1—Sn1—S2—C13 | 39.2 (4) | S3—Sn1—C7—C12 | 24.6 (5) |
C7—Sn1—S2—C13 | −96.1 (2) | S1—Sn1—C7—C12 | −132.9 (4) |
S3—Sn1—S2—C13 | 169.3 (1) | S2—Sn1—C7—C12 | −64.9 (5) |
S1—Sn1—S2—C13 | 4.9 (1) | S4—Sn1—C7—C12 | 8.7 (8) |
S4—Sn1—S2—C13 | 101.6 (1) | C12—C7—C8—C9 | 1.2 (8) |
C1—Sn1—S3—C17 | 78.1 (2) | Sn1—C7—C8—C9 | −179.9 (4) |
C7—Sn1—S3—C17 | −177.7 (2) | C7—C8—C9—C10 | −1.7 (9) |
S1—Sn1—S3—C17 | −53.4 (2) | C8—C9—C10—C11 | 1 (1) |
S2—Sn1—S3—C17 | −86.5 (2) | C9—C10—C11—C12 | 1 (1) |
S4—Sn1—S3—C17 | −3.0 (2) | C10—C11—C12—C7 | −1 (1) |
C1—Sn1—S4—C17 | −102.5 (2) | C8—C7—C12—C11 | 0.2 (9) |
C7—Sn1—S4—C17 | 20.2 (5) | Sn1—C7—C12—C11 | −178.6 (5) |
S3—Sn1—S4—C17 | 3.1 (2) | C14—N1—C13—S2 | −1.8 (4) |
S1—Sn1—S4—C17 | 162.5 (2) | C15—N1—C13—S2 | −177.9 (2) |
S2—Sn1—S4—C17 | 95.0 (2) | C14—N1—C13—S1 | 179.2 (2) |
C7—Sn1—C1—C6 | 92.6 (5) | C15—N1—C13—S1 | 3.1 (4) |
S3—Sn1—C1—C6 | −169.5 (4) | Sn1—S2—C13—N1 | 173.1 (2) |
S1—Sn1—C1—C6 | −9.5 (5) | Sn1—S2—C13—S1 | −7.9 (1) |
S2—Sn1—C1—C6 | −41.2 (7) | Sn1—S1—C13—N1 | −173.1 (2) |
S4—Sn1—C1—C6 | −103.1 (4) | Sn1—S1—C13—S2 | 7.9 (1) |
C7—Sn1—C1—C2 | −85.2 (5) | C13—N1—C15—C16 | −114.5 (9) |
S3—Sn1—C1—C2 | 12.7 (5) | C14—N1—C15—C16 | 69 (1) |
S1—Sn1—C1—C2 | 172.6 (4) | N1—C15—C16—O1 | −172.7 (7) |
S2—Sn1—C1—C2 | 140.9 (4) | C19—N2—C17—S4 | 178.5 (4) |
S4—Sn1—C1—C2 | 79.0 (4) | C18—N2—C17—S4 | −1.8 (9) |
C6—C1—C2—C3 | 0.7 (9) | C19—N2—C17—S3 | −1.3 (7) |
Sn1—C1—C2—C3 | 178.7 (5) | C18—N2—C17—S3 | 178.5 (5) |
C1—C2—C3—C4 | 0 (1) | Sn1—S4—C17—N2 | 175.4 (5) |
C2—C3—C4—C5 | −1 (1) | Sn1—S4—C17—S3 | −4.9 (3) |
C3—C4—C5—C6 | 2 (1) | Sn1—S3—C17—N2 | −175.0 (4) |
C2—C1—C6—C5 | −0.1 (9) | Sn1—S3—C17—S4 | 5.2 (3) |
Sn1—C1—C6—C5 | −178.0 (5) | C17—N2—C19—C20 | −89.2 (7) |
C4—C5—C6—C1 | −1 (1) | C18—N2—C19—C20 | 91.0 (7) |
C1—Sn1—C7—C8 | −49.6 (4) | N2—C19—C20—O2 | −58.3 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1a···O2i | 0.96 | 2.26 | 2.703 (8) | 107 |
O2—H2a···O1i | 0.96 | 2.21 | 2.703 (8) | 110 |
C15—H15a···S1 | 0.97 | 2.44 | 3.025 (8) | 118 |
C19—H19b···S3 | 0.97 | 2.52 | 2.958 (7) | 107 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Sn(C6H5)2(C4H8NOS2)] |
Mr | 573.36 |
Crystal system, space group | Monoclinic, P2/c |
Temperature (K) | 298 |
a, b, c (Å) | 8.9931 (1), 12.2068 (1), 22.6703 (3) |
β (°) | 92.507 (1) |
V (Å3) | 2486.29 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.38 |
Crystal size (mm) | 0.26 × 0.22 × 0.16 |
Data collection | |
Diffractometer | Siemens CCD area-detector diffractometer |
Absorption correction | Empirical (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.715, 0.809 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17084, 6025, 4060 |
Rint | 0.087 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.146, 0.98 |
No. of reflections | 6025 |
No. of parameters | 262 |
No. of restraints | 6 |
H-atom treatment | Riding |
Δρmax, Δρmin (e Å−3) | 1.22, −1.77 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.
Sn1—C1 | 2.164 (5) | Sn1—S2 | 2.641 (1) |
Sn1—C7 | 2.177 (5) | Sn1—S3 | 2.550 (1) |
Sn1—S1 | 2.614 (1) | Sn1—S4 | 2.748 (2) |
C1—Sn1—C7 | 102.7 (2) | C7—Sn1—S4 | 161.6 (2) |
C1—Sn1—S1 | 95.2 (1) | S1—Sn1—S2 | 68.2 (1) |
C1—Sn1—S2 | 160.2 (1) | S1—Sn1—S3 | 152.9 (1) |
C1—Sn1—S3 | 103.2 (1) | S1—Sn1—S4 | 93.8 (1) |
C1—Sn1—S4 | 87.0 (1) | S2—Sn1—S3 | 89.4 (1) |
C7—Sn1—S1 | 100.7 (1) | S2—Sn1—S4 | 83.7 (1) |
C7—Sn1—S2 | 91.3 (1) | S3—Sn1—S4 | 67.8 (1) |
C7—Sn1—S3 | 94.6 (1) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1a···O2i | 0.96 | 2.26 | 2.703 (8) | 107 |
O2—H2a···O1i | 0.96 | 2.21 | 2.703 (8) | 110 |
C15—H15a···S1 | 0.97 | 2.44 | 3.025 (8) | 118 |
C19—H19b···S3 | 0.97 | 2.52 | 2.958 (7) | 107 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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Six-coordinate bis-chelated diaryltin compounds generally adopt a cis-octahedral geometry (Ng et al., 1987). The bond dimensions of the Sn atom in the title compound, (I), are similar to those found in the symmetrical compound, diphenyltin bis[bis(2-hydroxyethyl)dithiocarbamate] (Farina et al., 2000).