2,2'-[1,2-Phenyl­enebis­(methyl­ene­thio)]­bis(5-methyl-1,3,4-thia­diazo­le)

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)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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]

Crystal data

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) Å^3	Block, colorless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.029	w = 1/[σ^2(Fo^2) + (0.0345P)^2 + 1.2785P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C5^i	1.402 (4)
C3—N2	1.295 (3)	C6—C7	1.381 (3)
C3—S1	1.722 (2)	C7—C7^i	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)	C5^i—C5—C4	122.03 (11)
C1—C2—S1	122.07 (17)	C7—C6—C5	121.04 (19)
N2—C3—S1	114.39 (15)	C7^i—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—C5^i	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—C5^i	82.9 (2)	N2—C3—S1—C2	−0.70 (16)
C5^i—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—C7^i	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.