organic compounds
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°.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014432/bh2091sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014432/bh2091Isup2.hkl |
CCDC reference: 646724
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (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
Computing details top
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 top
Crystal data top
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) Å3 | 0.36 × 0.24 × 0.07 mm |
Z = 4 |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.111 | w = 1/[σ2(Fo2) + (0.0491P)2 + 0.0655P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/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 (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
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) |