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A new polymorph of 2,5-bis­(4-pyrid­yl)-1,3,4-thia­diazole, C12H8N4S, obtained under hydro­thermal conditions, is described. In this structure, the two terminal pyrid­yl groups are inclined to the central thia­diazole ring with dihedral angles of 6.47 (2) and 29.95 (5)°, and the dihedral angle between the pyrid­yl ring planes is 23.65 (6)°. An inter­molecular C—H...N weak inter­action is observed. The structural differences of two polymorphs of 2,5-bis­(4-pyrid­yl)-1,3,4-thia­diazole are also discussed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805022142/ww6408sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805022142/ww6408Isup2.hkl
Contains datablock I

CCDC reference: 282698

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.032
  • wR factor = 0.101
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.770 1.000 Tmin(prime) and Tmax expected: 0.917 0.978 RR(prime) = 0.821 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K 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 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: APEX-II (Bruker, 2003); cell refinement: APEX-II; 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(4-pyridyl)-1,3,4-thiadiazole top
Crystal data top
C12H8N4SF(000) = 496
Mr = 240.28Dx = 1.504 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1940 reflections
a = 13.395 (2) Åθ = 3.2–27.3°
b = 7.1833 (11) ŵ = 0.28 mm1
c = 11.4151 (18) ÅT = 293 K
β = 104.948 (2)°Lamellar, pale yellow
V = 1061.2 (3) Å30.30 × 0.24 × 0.08 mm
Z = 4
Data collection top
Bruker APEX-II CCD area-detector
diffractometer
1862 independent reflections
Radiation source: fine-focus sealed tube1515 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.770, Tmax = 1.000k = 84
5414 measured reflectionsl = 1313
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.0679P)2 + 0.0172P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
1862 reflectionsΔρmax = 0.23 e Å3
155 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.009 (2)
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
xyzUiso*/Ueq
S10.70555 (3)0.13019 (6)0.87463 (4)0.0411 (2)
N11.11893 (11)0.1743 (2)0.93303 (14)0.0464 (4)
N20.75023 (11)0.1460 (2)0.67143 (14)0.0462 (4)
N30.64493 (12)0.1409 (2)0.64481 (14)0.0472 (4)
N40.28675 (12)0.1179 (2)0.71677 (16)0.0506 (4)
C10.97174 (13)0.0817 (2)0.77593 (15)0.0390 (4)
H10.94610.02530.70080.047*
C21.07654 (13)0.0957 (3)0.82551 (17)0.0432 (5)
H21.12040.04770.78180.052*
C31.05425 (13)0.2411 (2)0.99306 (16)0.0453 (5)
H31.08210.29611.06810.054*
C40.94792 (13)0.2340 (2)0.95096 (15)0.0404 (4)
H40.90600.28300.99680.048*
C50.90482 (13)0.1529 (2)0.83938 (15)0.0339 (4)
C60.79231 (13)0.1427 (2)0.78771 (16)0.0347 (4)
C70.61030 (13)0.1342 (2)0.74097 (15)0.0354 (4)
C80.49930 (12)0.1287 (2)0.73569 (16)0.0355 (4)
C90.46184 (15)0.1391 (2)0.83724 (18)0.0462 (5)
H90.50690.15030.91400.055*
C100.35611 (15)0.1328 (3)0.82321 (18)0.0510 (5)
H100.33210.13940.89260.061*
C110.32375 (14)0.1087 (3)0.61987 (18)0.0472 (5)
H110.27670.09910.54440.057*
C120.42750 (14)0.1123 (2)0.62359 (17)0.0420 (4)
H120.44910.10400.55260.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0303 (3)0.0582 (3)0.0354 (3)0.00014 (18)0.00981 (19)0.00226 (19)
N10.0340 (8)0.0565 (9)0.0473 (9)0.0046 (7)0.0081 (7)0.0035 (7)
N20.0293 (8)0.0719 (11)0.0374 (8)0.0008 (7)0.0085 (7)0.0038 (7)
N30.0293 (8)0.0738 (11)0.0384 (8)0.0022 (7)0.0085 (7)0.0042 (7)
N40.0335 (9)0.0587 (10)0.0617 (11)0.0001 (7)0.0162 (8)0.0020 (8)
C10.0380 (10)0.0451 (9)0.0355 (9)0.0012 (8)0.0124 (7)0.0013 (7)
C20.0329 (10)0.0542 (11)0.0455 (11)0.0020 (8)0.0155 (8)0.0032 (8)
C30.0401 (10)0.0525 (11)0.0399 (10)0.0071 (8)0.0041 (8)0.0018 (8)
C40.0382 (10)0.0443 (10)0.0403 (9)0.0003 (7)0.0131 (7)0.0036 (7)
C50.0293 (9)0.0365 (9)0.0367 (9)0.0014 (6)0.0096 (7)0.0031 (7)
C60.0304 (9)0.0378 (9)0.0370 (9)0.0002 (7)0.0107 (7)0.0017 (7)
C70.0303 (9)0.0390 (9)0.0375 (9)0.0009 (7)0.0097 (7)0.0024 (7)
C80.0293 (9)0.0344 (9)0.0433 (10)0.0005 (7)0.0100 (8)0.0016 (7)
C90.0374 (10)0.0601 (12)0.0419 (10)0.0019 (8)0.0112 (8)0.0043 (8)
C100.0427 (11)0.0654 (13)0.0513 (12)0.0027 (9)0.0239 (10)0.0040 (9)
C110.0327 (10)0.0577 (12)0.0489 (11)0.0020 (8)0.0062 (8)0.0027 (9)
C120.0342 (10)0.0527 (11)0.0397 (10)0.0032 (7)0.0106 (8)0.0026 (8)
Geometric parameters (Å, º) top
S1—C61.7141 (17)C3—H30.9300
S1—C71.7182 (18)C4—C51.384 (2)
N1—C31.325 (2)C4—H40.9300
N1—C21.337 (2)C5—C61.472 (2)
N2—C61.302 (2)C7—C81.473 (2)
N2—N31.365 (2)C8—C91.379 (3)
N3—C71.298 (2)C8—C121.393 (2)
N4—C111.325 (3)C9—C101.384 (3)
N4—C101.330 (3)C9—H90.9300
C1—C21.375 (2)C10—H100.9300
C1—C51.387 (2)C11—C121.379 (3)
C1—H10.9300C11—H110.9300
C2—H20.9300C12—H120.9300
C3—C41.382 (2)
C6—S1—C786.79 (8)N2—C6—S1114.29 (14)
C3—N1—C2116.62 (16)C5—C6—S1123.21 (13)
C6—N2—N3112.18 (15)N3—C7—C8122.92 (16)
C7—N3—N2112.76 (15)N3—C7—S1113.96 (13)
C11—N4—C10116.29 (16)C8—C7—S1123.12 (13)
C2—C1—C5119.13 (16)C9—C8—C12117.51 (16)
C2—C1—H1120.4C9—C8—C7123.13 (16)
C5—C1—H1120.4C12—C8—C7119.36 (16)
N1—C2—C1123.72 (17)C8—C9—C10118.96 (18)
N1—C2—H2118.1C8—C9—H9120.5
C1—C2—H2118.1C10—C9—H9120.5
N1—C3—C4124.03 (17)N4—C10—C9124.13 (18)
N1—C3—H3118.0N4—C10—H10117.9
C4—C3—H3118.0C9—C10—H10117.9
C3—C4—C5118.91 (16)N4—C11—C12124.33 (17)
C3—C4—H4120.5N4—C11—H11117.8
C5—C4—H4120.5C12—C11—H11117.8
C4—C5—C1117.60 (16)C11—C12—C8118.76 (17)
C4—C5—C6122.05 (15)C11—C12—H12120.6
C1—C5—C6120.35 (15)C8—C12—H12120.6
N2—C6—C5122.49 (16)
C6—N2—N3—C70.1 (2)N2—N3—C7—C8179.64 (14)
C3—N1—C2—C10.1 (3)N2—N3—C7—S10.87 (19)
C5—C1—C2—N10.2 (3)C6—S1—C7—N31.04 (13)
C2—N1—C3—C40.2 (3)C6—S1—C7—C8179.48 (13)
N1—C3—C4—C50.0 (3)N3—C7—C8—C9173.72 (16)
C3—C4—C5—C10.3 (2)S1—C7—C8—C96.8 (2)
C3—C4—C5—C6179.06 (15)N3—C7—C8—C126.3 (2)
C2—C1—C5—C40.4 (2)S1—C7—C8—C12173.16 (13)
C2—C1—C5—C6179.00 (15)C12—C8—C9—C100.0 (2)
N3—N2—C6—C5178.05 (14)C7—C8—C9—C10179.97 (15)
N3—N2—C6—S10.71 (18)C11—N4—C10—C90.1 (3)
C4—C5—C6—N2149.13 (17)C8—C9—C10—N40.3 (3)
C1—C5—C6—N230.2 (2)C10—N4—C11—C120.5 (3)
C4—C5—C6—S129.5 (2)N4—C11—C12—C80.7 (3)
C1—C5—C6—S1151.11 (14)C9—C8—C12—C110.4 (2)
C7—S1—C6—N20.98 (13)C7—C8—C12—C11179.56 (15)
C7—S1—C6—C5177.77 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N4i0.932.573.361 (3)143
Symmetry code: (i) x+1, y, z.
 

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