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The title compound, C10H14N4S2, obtained from the alkylation of methimazole with ethylene dibromide, is centrosymmetric and the two imidazole-2-thione ring moieties are anti-parallel to one another.
Supporting information
CCDC reference: 206791
Key indicators
- Single-crystal X-ray study
- T = 288 K
- Mean (C-C) = 0.004 Å
- R factor = 0.039
- wR factor = 0.104
- Data-to-parameter ratio = 14.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
1,1'-(1,2-Ethanediyl)bis(2,3-dihydro-3-methyl-1
H-imidazole-2-thione)
top
Crystal data top
C10H14N4S2 | F(000) = 268 |
Mr = 254.37 | Dx = 1.365 Mg m−3 |
Monoclinic, P21/c | Melting point = 467–468.5 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 4.667 (1) Å | Cell parameters from 27 reflections |
b = 19.720 (3) Å | θ = 4.8–13.6° |
c = 7.037 (1) Å | µ = 0.41 mm−1 |
β = 107.08 (1)° | T = 288 K |
V = 619.0 (2) Å3 | Plate, colourless |
Z = 2 | 0.40 × 0.28 × 0.20 mm |
Data collection top
Siemens P4 diffractometer | 804 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ω scans | h = 0→5 |
Absorption correction: empirical (using intensity measurements) (SHELXS97; Sheldrick, 1990) | k = 0→23 |
Tmin = 0.860, Tmax = 0.921 | l = −8→8 |
1339 measured reflections | 3 standard reflections every 97 reflections |
1097 independent reflections | intensity decay: 2.9% |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0578P)2] where P = (Fo2 + 2Fc2)/3 |
1097 reflections | (Δ/σ)max < 0.001 |
74 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. The structure was solved by direct methods(Sheldrick, 1990) and successive
difference Fourier syntheses. Refinement of F2 against ALL
reflections. The weighted R-factor wR and goodness of fit
S are based on F2, conventional R-factors R are
based on F, with F set to zero for negative F2. The
threshold expression of F2 > σ(F2) is used only for
calculating R-factors(gt) etc. and is not relevant to the choice
of reflections for refinement. R-factors based on F2 are
statistically about twice as large as those based on F, and
R-factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S | 0.73870 (16) | 0.35819 (4) | 0.32720 (10) | 0.0483 (3) | |
N1 | 1.0288 (4) | 0.35026 (10) | 0.7244 (3) | 0.0364 (5) | |
N2 | 0.6764 (4) | 0.42550 (10) | 0.6515 (3) | 0.0351 (5) | |
C1 | 0.8145 (5) | 0.37769 (11) | 0.5692 (4) | 0.0335 (6) | |
C2 | 1.0220 (7) | 0.38040 (13) | 0.8990 (4) | 0.0477 (7) | |
H2 | 1.1459 | 0.3701 | 1.0254 | 0.057* | |
C3 | 0.8064 (6) | 0.42695 (14) | 0.8548 (4) | 0.0466 (7) | |
H3 | 0.7529 | 0.4553 | 0.9445 | 0.056* | |
C4 | 0.4371 (5) | 0.46939 (11) | 0.5390 (4) | 0.0400 (6) | |
H4A | 0.3183 | 0.4843 | 0.6235 | 0.048* | |
H4B | 0.3071 | 0.4443 | 0.4285 | 0.048* | |
C5 | 1.2262 (6) | 0.29465 (13) | 0.7078 (4) | 0.0506 (8) | |
H5A | 1.1246 | 0.2523 | 0.7067 | 0.061* | |
H5B | 1.4042 | 0.2958 | 0.8190 | 0.061* | |
H5C | 1.2796 | 0.2993 | 0.5867 | 0.061* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.0456 (4) | 0.0641 (5) | 0.0335 (4) | −0.0011 (4) | 0.0089 (3) | −0.0072 (3) |
N1 | 0.0343 (11) | 0.0357 (11) | 0.0377 (12) | 0.0028 (9) | 0.0081 (9) | 0.0053 (9) |
N2 | 0.0364 (11) | 0.0330 (11) | 0.0343 (12) | 0.0016 (9) | 0.0081 (9) | 0.0009 (9) |
C1 | 0.0313 (13) | 0.0323 (13) | 0.0366 (14) | −0.0043 (10) | 0.0096 (11) | 0.0043 (10) |
C2 | 0.0504 (17) | 0.0559 (17) | 0.0304 (14) | 0.0039 (14) | 0.0018 (12) | 0.0038 (12) |
C3 | 0.0541 (17) | 0.0499 (16) | 0.0347 (15) | 0.0032 (14) | 0.0111 (13) | −0.0073 (12) |
C4 | 0.0283 (13) | 0.0378 (14) | 0.0528 (16) | 0.0026 (11) | 0.0103 (12) | 0.0043 (12) |
C5 | 0.0438 (17) | 0.0422 (16) | 0.066 (2) | 0.0083 (13) | 0.0163 (15) | 0.0104 (13) |
Geometric parameters (Å, º) top
S—C1 | 1.679 (2) | C2—H2 | 0.9300 |
N1—C1 | 1.358 (3) | C3—H3 | 0.9300 |
N1—C2 | 1.374 (3) | C4—H4A | 0.9700 |
N1—C5 | 1.459 (3) | C4—H4B | 0.9700 |
N2—C1 | 1.364 (3) | C5—H5A | 0.9600 |
N2—C3 | 1.381 (3) | C5—H5B | 0.9600 |
N2—C4 | 1.451 (3) | C5—H5C | 0.9600 |
C2—C3 | 1.329 (4) | | |
| | | |
C1—N1—C2 | 110.0 (2) | C2—C3—N2 | 107.5 (2) |
C1—N1—C5 | 124.6 (2) | C2—C3—H3 | 126.3 |
C2—N1—C5 | 125.3 (2) | N2—C3—H3 | 126.3 |
C1—N2—C3 | 109.6 (2) | N2—C4—H4A | 109.5 |
C1—N2—C4 | 124.4 (2) | N2—C4—H4B | 109.5 |
C3—N2—C4 | 125.9 (2) | H4A—C4—H4B | 108.1 |
N1—C1—N2 | 105.2 (2) | N1—C5—H5A | 109.5 |
N1—C1—S | 127.63 (19) | N1—C5—H5B | 109.5 |
N2—C1—S | 127.16 (18) | H5A—C5—H5B | 109.5 |
C3—C2—N1 | 107.7 (2) | N1—C5—H5C | 109.5 |
C3—C2—H2 | 126.1 | H5A—C5—H5C | 109.5 |
N1—C2—H2 | 126.1 | H5B—C5—H5C | 109.5 |
| | | |
C2—N1—C1—N2 | 0.2 (3) | C4—N2—C1—S | −1.1 (3) |
C5—N1—C1—N2 | 177.4 (2) | C1—N1—C2—C3 | −0.4 (3) |
C2—N1—C1—S | 179.3 (2) | C5—N1—C2—C3 | −177.6 (2) |
C5—N1—C1—S | −3.6 (3) | N1—C2—C3—N2 | 0.4 (3) |
C3—N2—C1—N1 | 0.0 (3) | C1—N2—C3—C2 | −0.3 (3) |
C4—N2—C1—N1 | 177.93 (19) | C4—N2—C3—C2 | −178.2 (2) |
C3—N2—C1—S | −178.99 (19) | | |
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