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metal-organic compounds
The title compound, [Sn(C6H5)3(C6H12NS2)], has a long-range intramolecular SnS interaction of 3.0950 (10) Å, which allows the geometry of the Sn atom to be close to trigonal bipyramidal, with an axial C—Sn—S bond angle of 156.50 (6)°. The structural dimensions of the molecule are comparable with those of other triphenyltin–dithiocarbamate complexes.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804025784/cv6391sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804025784/cv6391Isup2.hkl |
CCDC reference: 255436
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.005 Å
- R factor = 0.028
- wR factor = 0.063
- Data-to-parameter ratio = 19.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Siemens, 1997); cell refinement: SAINT (Siemens, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
(N-Ethyl-N-propyldithiocarbamato)triphenyltin(IV) top
Crystal data top
[Sn(C6H5)3(C6H12NS2)] | F(000) = 1040 |
Mr = 512.28 | Dx = 1.419 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4395 (18) Å | Cell parameters from 983 reflections |
b = 26.225 (5) Å | θ = 2.2–26.5° |
c = 9.8059 (19) Å | µ = 1.25 mm−1 |
β = 98.954 (3)° | T = 273 K |
V = 2397.9 (8) Å3 | Block, colourless |
Z = 4 | 0.38 × 0.29 × 0.16 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4928 independent reflections |
Radiation source: fine-focus sealed tube | 4481 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.5°, θmin = 2.2° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −22→32 |
Tmin = 0.648, Tmax = 0.825 | l = −12→10 |
13102 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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0247P)2 + 0.9515P] where P = (Fo2 + 2Fc2)/3 |
4928 reflections | (Δ/σ)max < 0.001 |
255 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.634073 (16) | 0.081382 (6) | 0.208680 (16) | 0.04317 (6) | |
S1 | 0.81744 (7) | 0.12090 (2) | 0.38232 (7) | 0.05446 (16) | |
S2 | 0.57525 (8) | 0.19172 (3) | 0.29688 (8) | 0.06112 (18) | |
N1 | 0.8206 (2) | 0.21815 (8) | 0.4522 (2) | 0.0531 (5) | |
C1 | 0.7417 (3) | 0.18211 (9) | 0.3820 (2) | 0.0469 (5) | |
C2 | 0.7685 (4) | 0.27123 (10) | 0.4540 (3) | 0.0695 (8) | |
H2A | 0.7098 | 0.2788 | 0.3661 | 0.083* | |
H2B | 0.8500 | 0.2942 | 0.4650 | 0.083* | |
C3 | 0.6823 (4) | 0.28072 (13) | 0.5680 (4) | 0.0886 (11) | |
H3A | 0.5997 | 0.2588 | 0.5560 | 0.133* | |
H3B | 0.6518 | 0.3157 | 0.5654 | 0.133* | |
H3C | 0.7402 | 0.2737 | 0.6554 | 0.133* | |
C4 | 0.9661 (3) | 0.20913 (11) | 0.5261 (3) | 0.0578 (6) | |
H4A | 0.9747 | 0.1737 | 0.5547 | 0.069* | |
H4B | 0.9813 | 0.2301 | 0.6086 | 0.069* | |
C5 | 1.0805 (3) | 0.22104 (13) | 0.4395 (3) | 0.0726 (8) | |
H5A | 1.0722 | 0.2565 | 0.4110 | 0.087* | |
H5B | 1.0656 | 0.2001 | 0.3570 | 0.087* | |
C6 | 1.2293 (4) | 0.21159 (15) | 0.5169 (4) | 0.0921 (11) | |
H6A | 1.2458 | 0.2332 | 0.5968 | 0.138* | |
H6B | 1.2988 | 0.2190 | 0.4579 | 0.138* | |
H6C | 1.2380 | 0.1765 | 0.5452 | 0.138* | |
C7 | 0.5182 (3) | 0.10838 (11) | −0.0919 (3) | 0.0645 (7) | |
H7 | 0.4365 | 0.0921 | −0.0719 | 0.077* | |
C8 | 0.5217 (5) | 0.12657 (13) | −0.2244 (3) | 0.0880 (11) | |
H8 | 0.4426 | 0.1220 | −0.2927 | 0.106* | |
C9 | 0.6399 (6) | 0.15095 (14) | −0.2548 (4) | 0.0959 (14) | |
H9 | 0.6417 | 0.1629 | −0.3438 | 0.115* | |
C10 | 0.7564 (5) | 0.15796 (14) | −0.1543 (4) | 0.0921 (12) | |
H10 | 0.8367 | 0.1751 | −0.1749 | 0.110* | |
C11 | 0.7551 (3) | 0.13957 (12) | −0.0224 (3) | 0.0707 (8) | |
H11 | 0.8350 | 0.1441 | 0.0450 | 0.085* | |
C12 | 0.6354 (3) | 0.11436 (9) | 0.0102 (3) | 0.0491 (6) | |
C13 | 0.8031 (3) | −0.00604 (10) | 0.0932 (3) | 0.0552 (6) | |
H13 | 0.7854 | 0.0130 | 0.0123 | 0.066* | |
C14 | 0.8820 (3) | −0.05091 (12) | 0.0954 (3) | 0.0697 (8) | |
H14 | 0.9175 | −0.0615 | 0.0167 | 0.084* | |
C15 | 0.9073 (4) | −0.07926 (11) | 0.2130 (4) | 0.0745 (9) | |
H15 | 0.9591 | −0.1095 | 0.2143 | 0.089* | |
C16 | 0.8566 (3) | −0.06344 (12) | 0.3296 (3) | 0.0693 (8) | |
H16 | 0.8745 | −0.0828 | 0.4100 | 0.083* | |
C17 | 0.7789 (3) | −0.01881 (10) | 0.3274 (3) | 0.0545 (6) | |
H17 | 0.7448 | −0.0084 | 0.4070 | 0.065* | |
C18 | 0.7506 (2) | 0.01074 (9) | 0.2093 (2) | 0.0431 (5) | |
C19 | 0.4292 (2) | 0.06185 (10) | 0.2598 (2) | 0.0459 (5) | |
C20 | 0.4001 (3) | 0.01084 (10) | 0.2769 (3) | 0.0564 (6) | |
H20 | 0.4717 | −0.0133 | 0.2739 | 0.068* | |
C21 | 0.2649 (3) | −0.00480 (12) | 0.2986 (3) | 0.0665 (7) | |
H21 | 0.2470 | −0.0392 | 0.3107 | 0.080* | |
C22 | 0.1585 (3) | 0.02988 (13) | 0.3022 (3) | 0.0666 (8) | |
H22 | 0.0679 | 0.0192 | 0.3162 | 0.080* | |
C23 | 0.1853 (3) | 0.08044 (13) | 0.2853 (4) | 0.0736 (9) | |
H23 | 0.1127 | 0.1042 | 0.2875 | 0.088* | |
C25 | 0.3201 (3) | 0.09647 (12) | 0.2647 (3) | 0.0652 (7) | |
H25 | 0.3374 | 0.1310 | 0.2541 | 0.078* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.04024 (10) | 0.04253 (10) | 0.04691 (10) | 0.00008 (6) | 0.00733 (6) | 0.00087 (7) |
S1 | 0.0489 (3) | 0.0439 (3) | 0.0671 (4) | 0.0026 (3) | −0.0018 (3) | −0.0074 (3) |
S2 | 0.0565 (4) | 0.0513 (4) | 0.0721 (4) | 0.0061 (3) | −0.0010 (3) | −0.0012 (3) |
N1 | 0.0597 (13) | 0.0411 (11) | 0.0587 (12) | −0.0071 (9) | 0.0098 (10) | −0.0040 (9) |
C1 | 0.0521 (14) | 0.0431 (13) | 0.0465 (13) | −0.0024 (10) | 0.0115 (10) | 0.0003 (10) |
C2 | 0.083 (2) | 0.0419 (14) | 0.084 (2) | −0.0069 (14) | 0.0148 (16) | −0.0035 (14) |
C3 | 0.100 (3) | 0.067 (2) | 0.102 (3) | 0.0079 (19) | 0.025 (2) | −0.0221 (19) |
C4 | 0.0635 (17) | 0.0524 (15) | 0.0562 (15) | −0.0111 (12) | 0.0049 (12) | −0.0095 (12) |
C5 | 0.0657 (19) | 0.072 (2) | 0.082 (2) | −0.0157 (15) | 0.0167 (16) | −0.0003 (16) |
C6 | 0.066 (2) | 0.096 (3) | 0.115 (3) | −0.0056 (19) | 0.018 (2) | −0.009 (2) |
C7 | 0.078 (2) | 0.0527 (16) | 0.0603 (17) | 0.0010 (14) | 0.0041 (14) | 0.0030 (13) |
C8 | 0.137 (3) | 0.067 (2) | 0.0551 (18) | 0.011 (2) | −0.002 (2) | 0.0048 (15) |
C9 | 0.165 (4) | 0.067 (2) | 0.066 (2) | 0.029 (2) | 0.051 (3) | 0.0165 (17) |
C10 | 0.110 (3) | 0.075 (2) | 0.107 (3) | 0.016 (2) | 0.068 (3) | 0.024 (2) |
C11 | 0.0627 (18) | 0.0692 (19) | 0.086 (2) | 0.0049 (14) | 0.0301 (16) | 0.0143 (16) |
C12 | 0.0553 (14) | 0.0402 (13) | 0.0545 (14) | 0.0062 (10) | 0.0164 (11) | 0.0030 (10) |
C13 | 0.0611 (16) | 0.0579 (16) | 0.0468 (14) | 0.0000 (12) | 0.0095 (11) | −0.0028 (11) |
C14 | 0.0739 (19) | 0.0712 (19) | 0.0678 (19) | 0.0077 (15) | 0.0230 (15) | −0.0194 (16) |
C15 | 0.080 (2) | 0.0531 (17) | 0.092 (2) | 0.0193 (15) | 0.0179 (18) | −0.0008 (16) |
C16 | 0.076 (2) | 0.0581 (17) | 0.076 (2) | 0.0167 (14) | 0.0160 (16) | 0.0166 (15) |
C17 | 0.0588 (16) | 0.0553 (15) | 0.0513 (14) | 0.0080 (12) | 0.0143 (12) | 0.0033 (12) |
C18 | 0.0406 (12) | 0.0414 (12) | 0.0470 (13) | −0.0021 (9) | 0.0065 (9) | −0.0028 (10) |
C19 | 0.0404 (12) | 0.0517 (13) | 0.0459 (13) | −0.0014 (10) | 0.0077 (10) | −0.0021 (10) |
C20 | 0.0498 (14) | 0.0534 (15) | 0.0675 (17) | −0.0012 (11) | 0.0142 (12) | −0.0042 (12) |
C21 | 0.0627 (18) | 0.0623 (17) | 0.0771 (19) | −0.0165 (14) | 0.0187 (15) | −0.0012 (15) |
C22 | 0.0457 (15) | 0.091 (2) | 0.0657 (17) | −0.0144 (15) | 0.0171 (13) | −0.0062 (16) |
C23 | 0.0451 (15) | 0.081 (2) | 0.097 (2) | 0.0074 (14) | 0.0200 (15) | −0.0049 (18) |
C25 | 0.0504 (15) | 0.0556 (16) | 0.092 (2) | 0.0012 (12) | 0.0173 (14) | 0.0038 (15) |
Geometric parameters (Å, º) top
Sn1—S1 | 2.4600 (7) | C8—H8 | 0.9300 |
Sn1—S2 | 3.0950 (10) | C9—C10 | 1.370 (6) |
Sn1—C12 | 2.132 (2) | C9—H9 | 0.9300 |
Sn1—C19 | 2.134 (2) | C10—C11 | 1.382 (5) |
Sn1—C18 | 2.154 (2) | C10—H10 | 0.9300 |
S1—C1 | 1.757 (2) | C11—C12 | 1.389 (4) |
S2—C1 | 1.679 (3) | C11—H11 | 0.9300 |
N1—C1 | 1.328 (3) | C13—C18 | 1.383 (3) |
N1—C4 | 1.469 (3) | C13—C14 | 1.391 (4) |
N1—C2 | 1.478 (3) | C13—H13 | 0.9300 |
C2—C3 | 1.502 (5) | C14—C15 | 1.362 (5) |
C2—H2A | 0.9700 | C14—H14 | 0.9300 |
C2—H2B | 0.9700 | C15—C16 | 1.370 (5) |
C3—H3A | 0.9600 | C15—H15 | 0.9300 |
C3—H3B | 0.9600 | C16—C17 | 1.380 (4) |
C3—H3C | 0.9600 | C16—H16 | 0.9300 |
C4—C5 | 1.506 (4) | C17—C18 | 1.384 (3) |
C4—H4A | 0.9700 | C17—H17 | 0.9300 |
C4—H4B | 0.9700 | C19—C25 | 1.379 (4) |
C5—C6 | 1.510 (5) | C19—C20 | 1.381 (4) |
C5—H5A | 0.9700 | C20—C21 | 1.387 (4) |
C5—H5B | 0.9700 | C20—H20 | 0.9300 |
C6—H6A | 0.9600 | C21—C22 | 1.360 (4) |
C6—H6B | 0.9600 | C21—H21 | 0.9300 |
C6—H6C | 0.9600 | C22—C23 | 1.365 (4) |
C7—C12 | 1.380 (4) | C22—H22 | 0.9300 |
C7—C8 | 1.389 (4) | C23—C25 | 1.384 (4) |
C7—H7 | 0.9300 | C23—H23 | 0.9300 |
C8—C9 | 1.359 (6) | C25—H25 | 0.9300 |
C12—Sn1—C19 | 116.49 (9) | C7—C8—H8 | 119.8 |
C12—Sn1—C18 | 106.03 (9) | C8—C9—C10 | 120.0 (3) |
C19—Sn1—C18 | 105.89 (9) | C8—C9—H9 | 120.0 |
C12—Sn1—S1 | 110.95 (7) | C10—C9—H9 | 120.0 |
C19—Sn1—S1 | 120.29 (7) | C9—C10—C11 | 120.2 (4) |
C18—Sn1—S1 | 93.23 (6) | C9—C10—H10 | 119.9 |
C18—Sn1—S2 | 156.50 (6) | C11—C10—H10 | 119.9 |
C1—S1—Sn1 | 98.11 (8) | C10—C11—C12 | 120.5 (3) |
C1—N1—C4 | 123.2 (2) | C10—C11—H11 | 119.7 |
C1—N1—C2 | 121.0 (2) | C12—C11—H11 | 119.7 |
C4—N1—C2 | 115.7 (2) | C7—C12—C11 | 118.4 (3) |
N1—C1—S2 | 123.86 (19) | C7—C12—Sn1 | 119.9 (2) |
N1—C1—S1 | 116.98 (19) | C11—C12—Sn1 | 121.6 (2) |
S2—C1—S1 | 119.15 (14) | C18—C13—C14 | 121.1 (3) |
N1—C2—C3 | 112.7 (3) | C18—C13—H13 | 119.5 |
N1—C2—H2A | 109.1 | C14—C13—H13 | 119.5 |
C3—C2—H2A | 109.1 | C15—C14—C13 | 119.8 (3) |
N1—C2—H2B | 109.1 | C15—C14—H14 | 120.1 |
C3—C2—H2B | 109.1 | C13—C14—H14 | 120.1 |
H2A—C2—H2B | 107.8 | C14—C15—C16 | 120.2 (3) |
C2—C3—H3A | 109.5 | C14—C15—H15 | 119.9 |
C2—C3—H3B | 109.5 | C16—C15—H15 | 119.9 |
H3A—C3—H3B | 109.5 | C15—C16—C17 | 119.9 (3) |
C2—C3—H3C | 109.5 | C15—C16—H16 | 120.1 |
H3A—C3—H3C | 109.5 | C17—C16—H16 | 120.1 |
H3B—C3—H3C | 109.5 | C16—C17—C18 | 121.4 (3) |
N1—C4—C5 | 112.7 (2) | C16—C17—H17 | 119.3 |
N1—C4—H4A | 109.1 | C18—C17—H17 | 119.3 |
C5—C4—H4A | 109.1 | C13—C18—C17 | 117.6 (2) |
N1—C4—H4B | 109.1 | C13—C18—Sn1 | 121.30 (18) |
C5—C4—H4B | 109.1 | C17—C18—Sn1 | 121.06 (17) |
H4A—C4—H4B | 107.8 | C25—C19—C20 | 118.0 (2) |
C4—C5—C6 | 112.0 (3) | C25—C19—Sn1 | 124.0 (2) |
C4—C5—H5A | 109.2 | C20—C19—Sn1 | 117.78 (18) |
C6—C5—H5A | 109.2 | C19—C20—C21 | 120.7 (3) |
C4—C5—H5B | 109.2 | C19—C20—H20 | 119.7 |
C6—C5—H5B | 109.2 | C21—C20—H20 | 119.7 |
H5A—C5—H5B | 107.9 | C22—C21—C20 | 120.5 (3) |
C5—C6—H6A | 109.5 | C22—C21—H21 | 119.8 |
C5—C6—H6B | 109.5 | C20—C21—H21 | 119.8 |
H6A—C6—H6B | 109.5 | C21—C22—C23 | 119.6 (3) |
C5—C6—H6C | 109.5 | C21—C22—H22 | 120.2 |
H6A—C6—H6C | 109.5 | C23—C22—H22 | 120.2 |
H6B—C6—H6C | 109.5 | C22—C23—C25 | 120.3 (3) |
C12—C7—C8 | 120.5 (3) | C22—C23—H23 | 119.8 |
C12—C7—H7 | 119.8 | C25—C23—H23 | 119.8 |
C8—C7—H7 | 119.8 | C19—C25—C23 | 120.9 (3) |
C9—C8—C7 | 120.4 (4) | C19—C25—H25 | 119.6 |
C9—C8—H8 | 119.8 | C23—C25—H25 | 119.6 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···S2 | 0.97 | 2.65 | 3.029 (3) | 104 |
C4—H4A···S1 | 0.97 | 2.49 | 2.949 (3) | 109 |
C25—H25···S2 | 0.93 | 2.73 | 3.450 (3) | 135 |
C4—H4B···S2i | 0.97 | 2.81 | 3.745 (3) | 162 |
Symmetry code: (i) x+1/2, −y+1/2, z+1/2. |
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