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In the title compound, [Sn(CH
3)
2(C
5H
10N
3S)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—H
N and intermolecular N—H
S hydrogen bonds. The latter link the molecules into dimers.
Supporting information
CCDC reference: 289776
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.005 Å
- R factor = 0.023
- wR factor = 0.062
- Data-to-parameter ratio = 22.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Sn1
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
2 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
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).
Chloro(1-isopropylidene-4-methyl-3-thiosemicarbazidato-
κ2N3,
S)dimethyltin(IV)
top
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. |
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