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In the crystal structure of the title compound, C7H5N3OS, the H atom of the thiol group is transferred to the neighboring N atom of the five-membered oxa­diazo­le ring. Intermolecular N—H...N interactions exist between adjacent mol­ecules, resulting in a one-dimensional (1D) supramolecular structure; π–π stacking interactions also exist between these 1D motifs.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001916/ww6163sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001916/ww6163Isup2.hkl
Contains datablock I

CCDC reference: 236059

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.092
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

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: SHELXTL (Bruker, 1998).

5-(4-Pyridyl)-1,3,4-oxadiazole-2(3H)-thione top
Crystal data top
C7H5N3OSF(000) = 368
Mr = 179.20Dx = 1.500 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 683 reflections
a = 4.869 (2) Åθ = 2.3–24.1°
b = 13.902 (5) ŵ = 0.36 mm1
c = 11.839 (4) ÅT = 293 K
β = 97.930 (6)°Prism, yellow
V = 793.6 (5) Å30.24 × 0.12 × 0.10 mm
Z = 4
Data collection top
Bruker SMART 1000
diffractometer
1112 reflections with I > 2σ(I)
ω scansRint = 0.040
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
θmax = 26.4°, θmin = 2.3°
Tmin = 0.955, Tmax = 0.968h = 64
4439 measured reflectionsk = 1717
1616 independent reflectionsl = 1412
Refinement top
Refinement on F20 restraints
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0325P)2 + 0.1604P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
1616 reflectionsΔρmax = 0.21 e Å3
109 parametersΔρmin = 0.22 e Å3
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. Full-MATRIX

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.20965 (15)0.47730 (5)0.22950 (6)0.0613 (3)
O10.5789 (3)0.58746 (11)0.35848 (13)0.0413 (4)
N10.2735 (4)0.66994 (13)0.25196 (15)0.0400 (5)
H10.13280.68530.20310.048*
N20.4459 (4)0.73605 (13)0.31172 (16)0.0410 (5)
N31.3180 (4)0.77811 (14)0.60246 (16)0.0445 (5)
C10.3472 (4)0.57973 (17)0.27766 (18)0.0393 (6)
C20.6246 (4)0.68426 (16)0.37347 (17)0.0336 (5)
C31.2454 (5)0.68580 (19)0.5961 (2)0.0488 (6)
H31.35130.64200.64300.059*
C41.0208 (5)0.65194 (17)0.52339 (19)0.0435 (6)
H40.97740.58680.52120.052*
C50.8613 (4)0.71618 (16)0.45382 (18)0.0346 (5)
C60.9336 (5)0.81280 (17)0.46052 (19)0.0424 (6)
H60.83030.85830.41540.051*
C71.1627 (5)0.83948 (17)0.5359 (2)0.0467 (6)
H71.21100.90420.54030.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0599 (5)0.0484 (4)0.0689 (5)0.0058 (3)0.0151 (3)0.0094 (4)
O10.0405 (9)0.0359 (9)0.0435 (9)0.0024 (7)0.0087 (7)0.0030 (7)
N10.0359 (11)0.0437 (12)0.0370 (11)0.0028 (9)0.0070 (8)0.0013 (9)
N20.0403 (11)0.0409 (11)0.0392 (11)0.0002 (9)0.0037 (9)0.0017 (9)
N30.0384 (11)0.0518 (13)0.0415 (12)0.0029 (10)0.0015 (9)0.0045 (10)
C10.0363 (13)0.0466 (14)0.0337 (13)0.0015 (11)0.0003 (10)0.0014 (11)
C20.0352 (12)0.0348 (12)0.0309 (12)0.0020 (10)0.0043 (9)0.0014 (11)
C30.0451 (14)0.0521 (16)0.0453 (14)0.0081 (13)0.0073 (11)0.0012 (12)
C40.0483 (15)0.0347 (14)0.0447 (15)0.0012 (11)0.0034 (11)0.0006 (11)
C50.0309 (12)0.0385 (13)0.0344 (12)0.0012 (10)0.0046 (10)0.0016 (10)
C60.0410 (13)0.0406 (14)0.0436 (14)0.0027 (11)0.0010 (11)0.0056 (11)
C70.0457 (15)0.0423 (15)0.0507 (16)0.0054 (11)0.0019 (12)0.0015 (11)
Geometric parameters (Å, º) top
S1—C11.642 (2)C2—C51.458 (3)
O1—C21.371 (2)C3—C41.378 (3)
O1—C11.379 (3)C3—H30.9300
N1—C11.328 (3)C4—C51.379 (3)
N1—N21.373 (2)C4—H40.9300
N1—H10.8600C5—C61.388 (3)
N2—C21.278 (3)C6—C71.380 (3)
N3—C71.325 (3)C6—H60.9300
N3—C31.330 (3)C7—H70.9300
C2—O1—C1105.59 (16)C4—C3—H3118.4
C1—N1—N2112.78 (18)C3—C4—C5119.0 (2)
C1—N1—H1123.6C3—C4—H4120.5
N2—N1—H1123.6C5—C4—H4120.5
C2—N2—N1103.71 (18)C4—C5—C6118.4 (2)
C7—N3—C3117.5 (2)C4—C5—C2121.4 (2)
N1—C1—O1104.75 (19)C6—C5—C2120.20 (19)
N1—C1—S1130.91 (17)C7—C6—C5118.2 (2)
O1—C1—S1124.33 (17)C7—C6—H6120.9
N2—C2—O1113.16 (18)C5—C6—H6120.9
N2—C2—C5128.0 (2)N3—C7—C6123.7 (2)
O1—C2—C5118.84 (18)N3—C7—H7118.1
N3—C3—C4123.1 (2)C6—C7—H7118.1
N3—C3—H3118.4
C1—N1—N2—C20.1 (3)C3—C4—C5—C60.3 (3)
N2—N1—C1—O10.2 (2)C3—C4—C5—C2178.7 (2)
N2—N1—C1—S1179.75 (18)N2—C2—C5—C4173.3 (2)
C2—O1—C1—N10.4 (2)O1—C2—C5—C47.1 (3)
C2—O1—C1—S1179.54 (16)N2—C2—C5—C67.7 (4)
N1—N2—C2—O10.4 (2)O1—C2—C5—C6171.9 (2)
N1—N2—C2—C5179.2 (2)C4—C5—C6—C70.5 (3)
C1—O1—C2—N20.5 (2)C2—C5—C6—C7178.6 (2)
C1—O1—C2—C5179.15 (18)C3—N3—C7—C60.6 (4)
C7—N3—C3—C40.7 (4)C5—C6—C7—N30.0 (4)
N3—C3—C4—C50.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N3i0.861.882.737 (3)177
Symmetry code: (i) x3/2, y+3/2, z1/2.
 

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