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

The title mol­ecule, C₁₂H₈N₄S, possesses anti­bacterial properties and is a potential ligand for metal complexes. The dihedral angles between the pyridyl rings and the central thia­diazole ring are less than 10°.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.111
• Data-to-parameter ratio = 16.0

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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

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

Crystal data

C12H8N4S	F(000) = 496
Mr = 240.29	Dx = 1.464 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1268 reflections
a = 12.872 (2) Å	θ = 3.2–22.4°
b = 11.0157 (19) Å	µ = 0.28 mm^−1
c = 7.8170 (13) Å	T = 291 K
β = 100.405 (2)°	Block, colourless
V = 1090.2 (3) Å^3	0.36 × 0.24 × 0.07 mm
Z = 4

Data collection

Bruker SMART APEXII diffractometer	2480 independent reflections
Radiation source: fine-focus sealed tube	1607 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→16
Tmin = 0.907, Tmax = 0.981	k = −12→14
7069 measured reflections	l = −10→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0491P)^2 + 0.0655P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2480 reflections	Δρmax = 0.21 e Å^−3
155 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (14)

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

	x	y	z	Uiso*/Ueq
S1	0.59978 (4)	0.85764 (4)	0.84368 (7)	0.0523 (2)
N1	0.96414 (14)	0.73907 (18)	0.6939 (3)	0.0708 (6)
N2	0.66769 (14)	0.64330 (14)	0.8180 (2)	0.0599 (5)
N3	0.56693 (14)	0.63101 (14)	0.8517 (2)	0.0594 (5)
N4	0.27159 (14)	0.87171 (16)	0.9614 (2)	0.0618 (5)
C1	0.99272 (17)	0.8548 (2)	0.7123 (3)	0.0691 (7)
H1	1.0589	0.8763	0.6904	0.083*
C2	0.93024 (16)	0.9446 (2)	0.7619 (3)	0.0693 (7)
H2	0.9537	1.0245	0.7729	0.083*
C3	0.83263 (16)	0.91395 (19)	0.7950 (3)	0.0596 (6)
H3	0.7891	0.9729	0.8300	0.072*
C4	0.79946 (14)	0.79478 (18)	0.7757 (2)	0.0459 (5)
C5	0.86925 (16)	0.7110 (2)	0.7247 (3)	0.0583 (5)
H5	0.8478	0.6304	0.7116	0.070*
C6	0.69585 (14)	0.75625 (16)	0.8097 (2)	0.0440 (5)
C7	0.52175 (14)	0.73476 (16)	0.8696 (2)	0.0425 (4)
C8	0.41592 (14)	0.74513 (16)	0.9136 (2)	0.0436 (5)
C9	0.36241 (16)	0.64305 (17)	0.9557 (3)	0.0537 (5)
H9	0.3925	0.5664	0.9543	0.064*
C10	0.26449 (16)	0.65682 (19)	0.9993 (3)	0.0586 (6)
H10	0.2270	0.5896	1.0268	0.070*
C11	0.22255 (16)	0.7720 (2)	1.0018 (3)	0.0600 (6)
H11	0.1566	0.7804	1.0332	0.072*
C12	0.36602 (15)	0.85647 (17)	0.9178 (3)	0.0535 (5)
H12	0.4009	0.9251	0.8880	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0504 (3)	0.0334 (3)	0.0758 (4)	0.0028 (2)	0.0185 (2)	−0.0015 (2)
N1	0.0588 (12)	0.0634 (14)	0.0948 (15)	0.0107 (10)	0.0264 (10)	−0.0079 (11)
N2	0.0589 (11)	0.0387 (10)	0.0854 (13)	0.0044 (8)	0.0223 (9)	−0.0019 (9)
N3	0.0606 (11)	0.0350 (10)	0.0862 (13)	0.0038 (8)	0.0230 (9)	0.0003 (9)
N4	0.0598 (11)	0.0511 (11)	0.0796 (13)	0.0045 (9)	0.0260 (9)	0.0023 (9)
C1	0.0497 (13)	0.0693 (17)	0.0913 (17)	0.0044 (12)	0.0209 (11)	0.0024 (13)
C2	0.0547 (13)	0.0527 (14)	0.1042 (19)	−0.0002 (11)	0.0244 (12)	0.0001 (13)
C3	0.0537 (12)	0.0467 (13)	0.0809 (15)	0.0071 (10)	0.0188 (10)	−0.0014 (11)
C4	0.0476 (11)	0.0411 (11)	0.0490 (11)	0.0072 (9)	0.0084 (8)	0.0004 (9)
C5	0.0577 (12)	0.0465 (12)	0.0724 (14)	0.0072 (10)	0.0159 (10)	−0.0054 (11)
C6	0.0496 (11)	0.0364 (11)	0.0448 (11)	0.0069 (8)	0.0051 (8)	−0.0016 (8)
C7	0.0489 (10)	0.0370 (11)	0.0404 (10)	0.0008 (8)	0.0051 (8)	0.0005 (8)
C8	0.0492 (11)	0.0375 (11)	0.0432 (10)	−0.0009 (8)	0.0064 (8)	−0.0017 (8)
C9	0.0606 (13)	0.0376 (12)	0.0631 (13)	−0.0029 (9)	0.0120 (10)	0.0002 (10)
C10	0.0608 (13)	0.0516 (13)	0.0657 (14)	−0.0114 (10)	0.0172 (10)	0.0000 (11)
C11	0.0524 (12)	0.0666 (15)	0.0636 (14)	−0.0035 (11)	0.0177 (10)	0.0002 (12)
C12	0.0564 (12)	0.0406 (12)	0.0670 (13)	−0.0016 (9)	0.0201 (10)	0.0002 (10)

Geometric parameters (Å, º)

S1—C7	1.7193 (18)	C3—H3	0.9300
S1—C6	1.7222 (18)	C4—C5	1.395 (3)
N1—C5	1.324 (3)	C4—C6	1.469 (3)
N1—C1	1.327 (3)	C5—H5	0.9300
N2—C6	1.301 (2)	C7—C8	1.468 (2)
N2—N3	1.376 (2)	C8—C12	1.388 (2)
N3—C7	1.301 (2)	C8—C9	1.389 (2)
N4—C12	1.331 (3)	C9—C10	1.372 (3)
N4—C11	1.333 (3)	C9—H9	0.9300
C1—C2	1.375 (3)	C10—C11	1.380 (3)
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.370 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.380 (3)
C7—S1—C6	87.63 (9)	N2—C6—S1	113.47 (14)
C5—N1—C1	116.82 (19)	C4—C6—S1	122.77 (14)
C6—N2—N3	112.61 (16)	N3—C7—C8	123.03 (17)
C7—N3—N2	112.91 (16)	N3—C7—S1	113.38 (14)
C12—N4—C11	116.74 (18)	C8—C7—S1	123.56 (13)
N1—C1—C2	123.9 (2)	C12—C8—C9	117.30 (18)
N1—C1—H1	118.1	C12—C8—C7	121.81 (17)
C2—C1—H1	118.1	C9—C8—C7	120.88 (17)
C3—C2—C1	118.6 (2)	C10—C9—C8	119.10 (18)
C3—C2—H2	120.7	C10—C9—H9	120.4
C1—C2—H2	120.7	C8—C9—H9	120.4
C2—C3—C4	119.34 (19)	C9—C10—C11	118.96 (19)
C2—C3—H3	120.3	C9—C10—H10	120.5
C4—C3—H3	120.3	C11—C10—H10	120.5
C3—C4—C5	117.25 (18)	N4—C11—C10	123.4 (2)
C3—C4—C6	121.88 (17)	N4—C11—H11	118.3
C5—C4—C6	120.87 (18)	C10—C11—H11	118.3
N1—C5—C4	124.1 (2)	N4—C12—C8	124.43 (18)
N1—C5—H5	118.0	N4—C12—H12	117.8
C4—C5—H5	118.0	C8—C12—H12	117.8
N2—C6—C4	123.76 (17)
C6—N2—N3—C7	−0.6 (3)	N2—N3—C7—C8	−177.28 (16)
C5—N1—C1—C2	0.4 (4)	N2—N3—C7—S1	0.7 (2)
N1—C1—C2—C3	0.1 (4)	C6—S1—C7—N3	−0.52 (15)
C1—C2—C3—C4	−0.7 (3)	C6—S1—C7—C8	177.48 (16)
C2—C3—C4—C5	0.7 (3)	N3—C7—C8—C12	−174.54 (18)
C2—C3—C4—C6	179.80 (19)	S1—C7—C8—C12	7.6 (3)
C1—N1—C5—C4	−0.4 (3)	N3—C7—C8—C9	6.5 (3)
C3—C4—C5—N1	−0.2 (3)	S1—C7—C8—C9	−171.32 (14)
C6—C4—C5—N1	−179.22 (19)	C12—C8—C9—C10	−0.3 (3)
N3—N2—C6—C4	179.87 (16)	C7—C8—C9—C10	178.76 (18)
N3—N2—C6—S1	0.2 (2)	C8—C9—C10—C11	−0.6 (3)
C3—C4—C6—N2	−169.54 (19)	C12—N4—C11—C10	−0.3 (3)
C5—C4—C6—N2	9.5 (3)	C9—C10—C11—N4	1.0 (3)
C3—C4—C6—S1	10.1 (3)	C11—N4—C12—C8	−0.7 (3)
C5—C4—C6—S1	−170.87 (15)	C9—C8—C12—N4	1.0 (3)
C7—S1—C6—N2	0.18 (15)	C7—C8—C12—N4	−178.03 (18)
C7—S1—C6—C4	−179.52 (16)