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The title compound (PBT), C14H14N4S4, possesses C2 symmetry, with the twofold axis bisecting the central benzene ring. The two terminal 2-(5-methyl-1,3,4-thiodiazolyl)thio groups adopt a trans conformation with respect to the benzene moiety, and the dihedral angle between the two thiodiazole planes is 61.3 (2)°, while that between the thiodiazole and benzene planes is 79.4 (5)°.
Supporting information
CCDC reference: 202991
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.029
- wR factor = 0.078
- Data-to-parameter ratio = 14.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
2,2'-[1,2-phenylenebis(methylenethio)]bis[5-methyl-1,3,4-thiadiazole]
top
Crystal data top
C14H14N4S4 | F(000) = 760 |
Mr = 366.53 | Dx = 1.429 Mg m−3 |
Monoclinic, C2/c | Melting point = 387–388 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 18.10 (1) Å | Cell parameters from 774 reflections |
b = 9.239 (5) Å | θ = 2.5–26.3° |
c = 11.216 (6) Å | µ = 0.56 mm−1 |
β = 114.764 (8)° | T = 293 K |
V = 1703.3 (16) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1497 independent reflections |
Radiation source: fine-focus sealed tube | 1242 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.000 |
φ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: empirical (using intensity measurements) multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995) | h = −21→19 |
Tmin = 0.851, Tmax = 0.897 | k = −11→10 |
2152 measured reflections | l = −13→13 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.029 | w = 1/[σ2(Fo2) + (0.0345P)2 + 1.2785P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.078 | (Δ/σ)max = 0.002 |
S = 1.08 | Δρmax = 0.16 e Å−3 |
1497 reflections | Δρmin = −0.27 e Å−3 |
101 parameters | |
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. 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 | |
C1 | 0.21874 (17) | 0.7285 (3) | 1.1845 (3) | 0.0698 (7) | |
H1A | 0.2591 | 0.7676 | 1.1591 | 0.105* | |
H1B | 0.2430 | 0.7084 | 1.2770 | 0.105* | |
H1C | 0.1755 | 0.7973 | 1.1651 | 0.105* | |
C2 | 0.18541 (12) | 0.5917 (2) | 1.1105 (2) | 0.0455 (5) | |
C3 | 0.11765 (12) | 0.3706 (2) | 1.01993 (18) | 0.0389 (5) | |
C4 | 0.08644 (13) | 0.1441 (2) | 0.8508 (2) | 0.0443 (5) | |
H4A | 0.0723 | 0.2155 | 0.7813 | 0.053* | |
H4B | 0.1445 | 0.1261 | 0.8853 | 0.053* | |
C5 | 0.04034 (11) | 0.0062 (2) | 0.79752 (18) | 0.0370 (4) | |
C6 | 0.07878 (13) | −0.1252 (2) | 0.8447 (2) | 0.0439 (5) | |
H6 | 0.1320 | −0.1260 | 0.9088 | 0.053* | |
C7 | 0.03924 (13) | −0.2548 (2) | 0.7977 (2) | 0.0483 (5) | |
H7 | 0.0657 | −0.3419 | 0.8307 | 0.058* | |
N1 | 0.20691 (11) | 0.5378 (2) | 1.02379 (19) | 0.0521 (5) | |
N2 | 0.16765 (10) | 0.40861 (19) | 0.97010 (17) | 0.0471 (4) | |
S1 | 0.11313 (4) | 0.48919 (6) | 1.13513 (6) | 0.05008 (19) | |
S2 | 0.06020 (4) | 0.21166 (6) | 0.98111 (6) | 0.05084 (19) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0786 (18) | 0.0645 (16) | 0.0708 (17) | −0.0309 (14) | 0.0358 (14) | −0.0233 (13) |
C2 | 0.0421 (11) | 0.0476 (12) | 0.0439 (11) | −0.0077 (9) | 0.0152 (10) | −0.0027 (9) |
C3 | 0.0390 (11) | 0.0389 (11) | 0.0357 (10) | −0.0003 (8) | 0.0127 (9) | 0.0009 (8) |
C4 | 0.0430 (11) | 0.0486 (12) | 0.0458 (11) | −0.0064 (9) | 0.0232 (9) | −0.0066 (10) |
C5 | 0.0394 (10) | 0.0398 (11) | 0.0382 (10) | −0.0017 (8) | 0.0225 (8) | −0.0028 (8) |
C6 | 0.0419 (11) | 0.0508 (13) | 0.0407 (11) | 0.0073 (9) | 0.0189 (9) | 0.0022 (9) |
C7 | 0.0669 (14) | 0.0389 (11) | 0.0474 (12) | 0.0111 (10) | 0.0320 (10) | 0.0060 (9) |
N1 | 0.0465 (10) | 0.0546 (11) | 0.0581 (11) | −0.0137 (9) | 0.0248 (9) | −0.0098 (9) |
N2 | 0.0447 (10) | 0.0478 (10) | 0.0507 (10) | −0.0073 (8) | 0.0220 (9) | −0.0064 (8) |
S1 | 0.0599 (4) | 0.0463 (3) | 0.0534 (3) | −0.0122 (3) | 0.0328 (3) | −0.0101 (2) |
S2 | 0.0630 (4) | 0.0460 (3) | 0.0542 (3) | −0.0161 (3) | 0.0350 (3) | −0.0114 (2) |
Geometric parameters (Å, º) top
C1—C2 | 1.494 (3) | C4—S2 | 1.825 (2) |
C2—N1 | 1.289 (3) | C5—C6 | 1.389 (3) |
C2—S1 | 1.729 (2) | C5—C5i | 1.402 (4) |
C3—N2 | 1.295 (3) | C6—C7 | 1.381 (3) |
C3—S1 | 1.722 (2) | C7—C7i | 1.375 (4) |
C3—S2 | 1.746 (2) | N1—N2 | 1.391 (2) |
C4—C5 | 1.504 (3) | | |
| | | |
N1—C2—C1 | 124.5 (2) | C6—C5—C4 | 118.92 (18) |
N1—C2—S1 | 113.39 (16) | C5i—C5—C4 | 122.03 (11) |
C1—C2—S1 | 122.07 (17) | C7—C6—C5 | 121.04 (19) |
N2—C3—S1 | 114.39 (15) | C7i—C7—C6 | 119.89 (12) |
N2—C3—S2 | 124.81 (15) | C2—N1—N2 | 113.40 (17) |
S1—C3—S2 | 120.77 (12) | C3—N2—N1 | 111.61 (17) |
C5—C4—S2 | 108.72 (13) | C3—S1—C2 | 87.21 (10) |
C6—C5—C5i | 119.06 (12) | C3—S2—C4 | 99.19 (9) |
| | | |
S2—C4—C5—C6 | −96.64 (19) | C2—N1—N2—C3 | −0.1 (3) |
S2—C4—C5—C5i | 82.9 (2) | N2—C3—S1—C2 | −0.70 (16) |
C5i—C5—C6—C7 | 1.1 (3) | S2—C3—S1—C2 | 177.62 (14) |
C4—C5—C6—C7 | −179.31 (17) | N1—C2—S1—C3 | 0.65 (17) |
C5—C6—C7—C7i | 0.4 (3) | C1—C2—S1—C3 | −179.0 (2) |
C1—C2—N1—N2 | 179.2 (2) | N2—C3—S2—C4 | −5.3 (2) |
S1—C2—N1—N2 | −0.5 (2) | S1—C3—S2—C4 | 176.60 (12) |
S1—C3—N2—N1 | 0.6 (2) | C5—C4—S2—C3 | −178.04 (14) |
S2—C3—N2—N1 | −177.65 (15) | | |
Symmetry code: (i) −x, y, −z+3/2. |
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