metal-organic compounds
In the title compound, [Sn(CH3)2(C5H10N3S)Cl], the 1-isopropylidene-4-methyl-3-thiosemicarbazidate ligand has a Z configuration and is chelated to the Sn atom through the S and hydrazinic N atoms in a distorted trigonal–bipyramidal pentacoordination environment. The molecular structure is stabilized by intramolecular C—HN and intermolecular N—HS hydrogen bonds. The latter link the molecules into dimers.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805034136/hk6049sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805034136/hk6049Isup2.hkl |
CCDC reference: 289776
Computing details top
Data collection: SMART (Bruker, 2000); cell refinement: SAINT; 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).
Crystal data top
[Sn(CH3)2(C5H10N3S)Cl] | Z = 2 |
Mr = 328.43 | F(000) = 324 |
Triclinic, P1 | Dx = 1.686 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5419 (16) Å | Cell parameters from 5170 reflections |
b = 7.7652 (16) Å | θ = 1.6–26.5° |
c = 12.703 (3) Å | µ = 2.31 mm−1 |
α = 95.485 (3)° | T = 273 K |
β = 93.302 (3)° | Block, colourless |
γ = 118.389 (3)° | 0.48 × 0.34 × 0.19 mm |
V = 647.0 (2) Å3 |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2656 independent reflections |
Radiation source: fine-focus sealed tube | 2498 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.5°, θmin = 1.6° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −9→9 |
Tmin = 0.403, Tmax = 0.668 | l = −15→15 |
6879 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)] = 0.023 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.062 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0311P)2 + 0.1504P] where P = (Fo2 + 2Fc2)/3 |
2656 reflections | (Δ/σ)max < 0.001 |
118 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.11356 (3) | 0.19519 (3) | 0.189477 (13) | 0.05365 (8) | |
Cl1 | −0.06985 (14) | −0.17554 (12) | 0.13677 (8) | 0.0816 (2) | |
S1 | 0.09368 (17) | 0.11359 (11) | 0.36877 (6) | 0.0804 (3) | |
N1 | 0.1803 (4) | 0.3493 (4) | 0.54710 (19) | 0.0702 (7) | |
H1D | 0.1302 | 0.2381 | 0.5715 | 0.084* | |
N2 | 0.2698 (3) | 0.5171 (3) | 0.40623 (17) | 0.0553 (5) | |
N3 | 0.2717 (3) | 0.5074 (3) | 0.29618 (18) | 0.0531 (5) | |
C1 | 0.2506 (6) | 0.5286 (6) | 0.6201 (3) | 0.0837 (10) | |
H1A | 0.2303 | 0.4971 | 0.6912 | 0.126* | |
H1B | 0.1760 | 0.5948 | 0.6012 | 0.126* | |
H1C | 0.3925 | 0.6135 | 0.6166 | 0.126* | |
C2 | 0.1907 (4) | 0.3507 (4) | 0.4417 (2) | 0.0566 (6) | |
C3 | 0.3600 (5) | 0.6764 (4) | 0.2626 (3) | 0.0626 (7) | |
C4 | 0.4557 (6) | 0.8665 (5) | 0.3358 (3) | 0.0882 (11) | |
H4A | 0.4439 | 0.8402 | 0.4081 | 0.132* | |
H4B | 0.3885 | 0.9412 | 0.3203 | 0.132* | |
H4C | 0.5965 | 0.9409 | 0.3261 | 0.132* | |
C5 | 0.3663 (6) | 0.6870 (5) | 0.1465 (3) | 0.0786 (9) | |
H5A | 0.3013 | 0.5556 | 0.1080 | 0.118* | |
H5B | 0.5049 | 0.7561 | 0.1322 | 0.118* | |
H5C | 0.2967 | 0.7560 | 0.1244 | 0.118* | |
C6 | 0.3802 (4) | 0.2363 (5) | 0.1235 (2) | 0.0672 (7) | |
H6A | 0.4784 | 0.3743 | 0.1346 | 0.101* | |
H6B | 0.3480 | 0.1894 | 0.0485 | 0.101* | |
H6C | 0.4350 | 0.1638 | 0.1575 | 0.101* | |
C7 | −0.1245 (5) | 0.2388 (5) | 0.1243 (3) | 0.0731 (8) | |
H7A | −0.0848 | 0.3769 | 0.1361 | 0.110* | |
H7B | −0.2440 | 0.1659 | 0.1579 | 0.110* | |
H7C | −0.1526 | 0.1932 | 0.0491 | 0.110* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.05193 (12) | 0.05788 (13) | 0.05084 (12) | 0.02701 (9) | 0.00749 (8) | 0.00294 (8) |
Cl1 | 0.0809 (5) | 0.0606 (4) | 0.0898 (6) | 0.0278 (4) | 0.0025 (4) | −0.0096 (4) |
S1 | 0.1178 (7) | 0.0517 (4) | 0.0562 (4) | 0.0273 (4) | 0.0183 (4) | 0.0095 (3) |
N1 | 0.0825 (17) | 0.0704 (15) | 0.0484 (13) | 0.0290 (13) | 0.0122 (11) | 0.0084 (11) |
N2 | 0.0571 (13) | 0.0554 (12) | 0.0511 (12) | 0.0258 (10) | 0.0085 (9) | 0.0039 (10) |
N3 | 0.0534 (12) | 0.0537 (12) | 0.0535 (12) | 0.0266 (10) | 0.0094 (9) | 0.0079 (9) |
C1 | 0.093 (2) | 0.095 (2) | 0.0552 (17) | 0.043 (2) | 0.0020 (16) | −0.0080 (16) |
C2 | 0.0560 (15) | 0.0614 (15) | 0.0512 (14) | 0.0276 (12) | 0.0079 (11) | 0.0063 (12) |
C3 | 0.0594 (16) | 0.0568 (15) | 0.0740 (19) | 0.0285 (13) | 0.0129 (13) | 0.0156 (13) |
C4 | 0.101 (3) | 0.0531 (16) | 0.099 (3) | 0.0282 (17) | 0.012 (2) | 0.0113 (17) |
C5 | 0.087 (2) | 0.077 (2) | 0.076 (2) | 0.0379 (18) | 0.0229 (17) | 0.0335 (17) |
C6 | 0.0578 (16) | 0.085 (2) | 0.0612 (17) | 0.0387 (15) | 0.0073 (13) | −0.0027 (15) |
C7 | 0.0609 (17) | 0.090 (2) | 0.074 (2) | 0.0447 (17) | −0.0013 (14) | −0.0054 (16) |
Geometric parameters (Å, º) top
Sn1—C6 | 2.117 (3) | C3—C5 | 1.487 (5) |
Sn1—C7 | 2.118 (3) | C3—C4 | 1.487 (5) |
Sn1—N3 | 2.361 (2) | C4—H4A | 0.9600 |
Sn1—S1 | 2.4158 (10) | C4—H4B | 0.9600 |
Sn1—Cl1 | 2.5273 (10) | C4—H4C | 0.9600 |
S1—C2 | 1.760 (3) | C5—H5A | 0.9600 |
N1—C2 | 1.346 (4) | C5—H5B | 0.9600 |
N1—C1 | 1.440 (4) | C5—H5C | 0.9600 |
N1—H1D | 0.8600 | C6—H6A | 0.9600 |
N2—C2 | 1.280 (4) | C6—H6B | 0.9600 |
N2—N3 | 1.394 (3) | C6—H6C | 0.9600 |
N3—C3 | 1.287 (4) | C7—H7A | 0.9600 |
C1—H1A | 0.9600 | C7—H7B | 0.9600 |
C1—H1B | 0.9600 | C7—H7C | 0.9600 |
C1—H1C | 0.9600 | ||
C6—Sn1—C7 | 128.61 (13) | N3—C3—C5 | 120.1 (3) |
C6—Sn1—N3 | 94.70 (10) | N3—C3—C4 | 122.5 (3) |
C7—Sn1—N3 | 92.54 (10) | C5—C3—C4 | 117.4 (3) |
C6—Sn1—S1 | 115.16 (9) | C3—C4—H4A | 109.5 |
C7—Sn1—S1 | 116.02 (10) | C3—C4—H4B | 109.5 |
N3—Sn1—S1 | 76.68 (6) | H4A—C4—H4B | 109.5 |
C6—Sn1—Cl1 | 94.03 (9) | C3—C4—H4C | 109.5 |
C7—Sn1—Cl1 | 95.49 (9) | H4A—C4—H4C | 109.5 |
N3—Sn1—Cl1 | 160.59 (6) | H4B—C4—H4C | 109.5 |
S1—Sn1—Cl1 | 83.92 (3) | C3—C5—H5A | 109.5 |
C2—S1—Sn1 | 100.20 (9) | C3—C5—H5B | 109.5 |
C2—N1—C1 | 121.9 (3) | H5A—C5—H5B | 109.5 |
C2—N1—H1D | 119.0 | C3—C5—H5C | 109.5 |
C1—N1—H1D | 119.0 | H5A—C5—H5C | 109.5 |
C2—N2—N3 | 115.6 (2) | H5B—C5—H5C | 109.5 |
C3—N3—N2 | 114.6 (2) | Sn1—C6—H6A | 109.5 |
C3—N3—Sn1 | 126.1 (2) | Sn1—C6—H6B | 109.5 |
N2—N3—Sn1 | 119.21 (15) | H6A—C6—H6B | 109.5 |
N1—C1—H1A | 109.5 | Sn1—C6—H6C | 109.5 |
N1—C1—H1B | 109.5 | H6A—C6—H6C | 109.5 |
H1A—C1—H1B | 109.5 | H6B—C6—H6C | 109.5 |
N1—C1—H1C | 109.5 | Sn1—C7—H7A | 109.5 |
H1A—C1—H1C | 109.5 | Sn1—C7—H7B | 109.5 |
H1B—C1—H1C | 109.5 | H7A—C7—H7B | 109.5 |
N2—C2—N1 | 118.7 (3) | Sn1—C7—H7C | 109.5 |
N2—C2—S1 | 127.7 (2) | H7A—C7—H7C | 109.5 |
N1—C2—S1 | 113.6 (2) | H7B—C7—H7C | 109.5 |
C6—Sn1—S1—C2 | 94.51 (14) | S1—Sn1—N3—N2 | −6.37 (17) |
C7—Sn1—S1—C2 | −80.72 (14) | Cl1—Sn1—N3—N2 | −4.7 (3) |
N3—Sn1—S1—C2 | 5.55 (11) | N3—N2—C2—N1 | −178.7 (2) |
Cl1—Sn1—S1—C2 | −173.89 (11) | N3—N2—C2—S1 | 2.6 (4) |
C2—N2—N3—C3 | −177.0 (3) | C1—N1—C2—N2 | 1.6 (5) |
C2—N2—N3—Sn1 | 4.2 (3) | C1—N1—C2—S1 | −179.5 (3) |
C6—Sn1—N3—C3 | 60.2 (3) | Sn1—S1—C2—N2 | −7.1 (3) |
C7—Sn1—N3—C3 | −68.9 (3) | Sn1—S1—C2—N1 | 174.1 (2) |
S1—Sn1—N3—C3 | 174.9 (2) | N2—N3—C3—C5 | −177.9 (3) |
Cl1—Sn1—N3—C3 | 176.63 (18) | Sn1—N3—C3—C5 | 0.9 (4) |
C6—Sn1—N3—N2 | −121.14 (19) | N2—N3—C3—C4 | 1.1 (4) |
C7—Sn1—N3—N2 | 109.8 (2) | Sn1—N3—C3—C4 | 179.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···N2 | 0.96 | 2.21 | 2.668 (4) | 108 |
N1—H1D···S1i | 0.86 | 2.65 | 3.501 (3) | 169 |
Symmetry code: (i) −x, −y, −z+1. |