2,5-Bis(4-pyridyl)-1,3,4-thia­diazo­le

In the structure of the title compound, C₁₂H₈N₄S, the mol­ecule has crystallographic C₂ symmetry. The two pyridine rings make dihedral angles of 21.8 (2)° with the mean plane of the central thia­diazo­le system, and the dihedral angle between the pyridine rings is 43.0 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.146
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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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: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXL97.

2,5-Bis(4-pyridyl)-1,3,4-thiadiazole

Crystal data

C12H8N4S	F(000) = 496
Mr = 240.28	Dx = 1.518 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 629 reflections
a = 26.179 (9) Å	θ = 3.6–26.2°
b = 5.8223 (17) Å	µ = 0.29 mm^−1
c = 7.169 (3) Å	T = 293 K
β = 105.855 (9)°	Block, colourless
V = 1051.1 (6) Å^3	0.20 × 0.18 × 0.12 mm
Z = 4

Data collection

Bruker SMART 1000 diffractometer	854 reflections with I > 2σ(I)
ω scans	Rint = 0.026
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 26.4°, θmin = 1.6°
Tmin = 0.945, Tmax = 0.966	h = −28→32
2924 measured reflections	k = −7→6
1081 independent reflections	l = −8→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H-atom parameters constrained
S = 1.19	w = 1/[σ^2(Fo^2) + (0.0872P)^2 + 0.0744P] where P = (Fo^2 + 2Fc^2)/3
1081 reflections	(Δ/σ)max < 0.001
78 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.0000	0.86747 (15)	0.2500	0.0350 (3)
N1	0.20650 (8)	0.7820 (4)	0.2628 (4)	0.0404 (6)
N2	0.02631 (8)	0.4433 (4)	0.2518 (4)	0.0359 (6)
C1	0.19126 (10)	0.5839 (5)	0.3244 (4)	0.0375 (7)
H1	0.2170	0.4721	0.3706	0.045*
C2	0.13960 (10)	0.5349 (4)	0.3238 (4)	0.0312 (6)
H2	0.1310	0.3935	0.3675	0.037*
C3	0.10078 (9)	0.7003 (4)	0.2568 (3)	0.0265 (6)
C4	0.11626 (10)	0.9092 (5)	0.1950 (4)	0.0342 (6)
H4	0.0917	1.0259	0.1507	0.041*
C5	0.16925 (11)	0.9391 (5)	0.2012 (4)	0.0388 (7)
H5	0.1792	1.0789	0.1593	0.047*
C6	0.04511 (9)	0.6508 (4)	0.2523 (4)	0.0265 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0265 (5)	0.0301 (5)	0.0509 (6)	0.000	0.0146 (4)	0.000
N1	0.0306 (12)	0.0446 (13)	0.0495 (15)	−0.0060 (10)	0.0165 (10)	−0.0038 (11)
N2	0.0224 (10)	0.0339 (12)	0.0530 (15)	0.0003 (9)	0.0129 (10)	−0.0012 (10)
C1	0.0257 (12)	0.0384 (14)	0.0498 (17)	0.0035 (11)	0.0129 (12)	−0.0013 (12)
C2	0.0295 (13)	0.0274 (13)	0.0386 (14)	−0.0001 (10)	0.0126 (11)	0.0007 (11)
C3	0.0219 (11)	0.0310 (13)	0.0275 (12)	0.0000 (10)	0.0082 (10)	−0.0038 (10)
C4	0.0326 (13)	0.0308 (14)	0.0380 (15)	0.0015 (11)	0.0078 (11)	0.0018 (11)
C5	0.0410 (15)	0.0368 (15)	0.0420 (16)	−0.0125 (12)	0.0171 (12)	−0.0016 (12)
C6	0.0217 (12)	0.0302 (13)	0.0278 (12)	0.0021 (9)	0.0071 (9)	0.0000 (10)

Geometric parameters (Å, º)

S1—C6^i	1.725 (2)	C2—H2	0.9300
S1—C6	1.725 (2)	N1—C5	1.322 (4)
C3—C2	1.387 (3)	C5—C4	1.387 (4)
C3—C4	1.392 (4)	C5—H5	0.9300
C3—C6	1.477 (3)	C4—H4	0.9300
C1—N1	1.334 (4)	N2—C6	1.305 (3)
C1—C2	1.381 (4)	N2—N2^i	1.371 (4)
C1—H1	0.9300
C6^i—S1—C6	86.02 (16)	N1—C5—C4	124.3 (2)
C2—C3—C4	117.9 (2)	N1—C5—H5	117.8
C2—C3—C6	119.8 (2)	C4—C5—H5	117.8
C4—C3—C6	122.3 (2)	C5—C4—C3	118.4 (2)
N1—C1—C2	124.0 (3)	C5—C4—H4	120.8
N1—C1—H1	118.0	C3—C4—H4	120.8
C2—C1—H1	118.0	C6—N2—N2^i	112.12 (13)
C1—C2—C3	118.8 (2)	N2—C6—C3	123.4 (2)
C1—C2—H2	120.6	N2—C6—S1	114.87 (17)
C3—C2—H2	120.6	C3—C6—S1	121.76 (18)
C5—N1—C1	116.7 (2)
N1—C1—C2—C3	−0.5 (4)	N2^i—N2—C6—C3	179.7 (3)
C4—C3—C2—C1	−0.6 (4)	N2^i—N2—C6—S1	0.4 (4)
C6—C3—C2—C1	179.2 (2)	C2—C3—C6—N2	−21.2 (4)
C2—C1—N1—C5	1.2 (4)	C4—C3—C6—N2	158.6 (3)
C1—N1—C5—C4	−0.8 (4)	C2—C3—C6—S1	158.03 (19)
N1—C5—C4—C3	−0.2 (4)	C4—C3—C6—S1	−22.2 (3)
C2—C3—C4—C5	0.9 (4)	C6^i—S1—C6—N2	−0.17 (14)
C6—C3—C4—C5	−178.9 (2)	C6^i—S1—C6—C3	−179.4 (3)

Symmetry code: (i) −x, y, −z+1/2.