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In the crystal structure of the title compound, C
7H
5N
3OS, 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
CCDC reference: 236059
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.092
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
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(3
H)-thione
top
Crystal data top
C7H5N3OS | F(000) = 368 |
Mr = 179.20 | Dx = 1.500 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 683 reflections |
a = 4.869 (2) Å | θ = 2.3–24.1° |
b = 13.902 (5) Å | µ = 0.36 mm−1 |
c = 11.839 (4) Å | T = 293 K |
β = 97.930 (6)° | Prism, yellow |
V = 793.6 (5) Å3 | 0.24 × 0.12 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker SMART 1000 diffractometer | 1112 reflections with I > 2σ(I) |
ω scans | Rint = 0.040 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | θmax = 26.4°, θmin = 2.3° |
Tmin = 0.955, Tmax = 0.968 | h = −6→4 |
4439 measured reflections | k = −17→17 |
1616 independent reflections | l = −14→12 |
Refinement top
Refinement on F2 | 0 restraints |
R[F2 > 2σ(F2)] = 0.045 | H-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 reflections | Δρmax = 0.21 e Å−3 |
109 parameters | Δρmin = −0.22 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.20965 (15) | 0.47730 (5) | 0.22950 (6) | 0.0613 (3) | |
O1 | 0.5789 (3) | 0.58746 (11) | 0.35848 (13) | 0.0413 (4) | |
N1 | 0.2735 (4) | 0.66994 (13) | 0.25196 (15) | 0.0400 (5) | |
H1 | 0.1328 | 0.6853 | 0.2031 | 0.048* | |
N2 | 0.4459 (4) | 0.73605 (13) | 0.31172 (16) | 0.0410 (5) | |
N3 | 1.3180 (4) | 0.77811 (14) | 0.60246 (16) | 0.0445 (5) | |
C1 | 0.3472 (4) | 0.57973 (17) | 0.27766 (18) | 0.0393 (6) | |
C2 | 0.6246 (4) | 0.68426 (16) | 0.37347 (17) | 0.0336 (5) | |
C3 | 1.2454 (5) | 0.68580 (19) | 0.5961 (2) | 0.0488 (6) | |
H3 | 1.3513 | 0.6420 | 0.6430 | 0.059* | |
C4 | 1.0208 (5) | 0.65194 (17) | 0.52339 (19) | 0.0435 (6) | |
H4 | 0.9774 | 0.5868 | 0.5212 | 0.052* | |
C5 | 0.8613 (4) | 0.71618 (16) | 0.45382 (18) | 0.0346 (5) | |
C6 | 0.9336 (5) | 0.81280 (17) | 0.46052 (19) | 0.0424 (6) | |
H6 | 0.8303 | 0.8583 | 0.4154 | 0.051* | |
C7 | 1.1627 (5) | 0.83948 (17) | 0.5359 (2) | 0.0467 (6) | |
H7 | 1.2110 | 0.9042 | 0.5403 | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0599 (5) | 0.0484 (4) | 0.0689 (5) | −0.0058 (3) | −0.0151 (3) | −0.0094 (4) |
O1 | 0.0405 (9) | 0.0359 (9) | 0.0435 (9) | 0.0024 (7) | −0.0087 (7) | −0.0030 (7) |
N1 | 0.0359 (11) | 0.0437 (12) | 0.0370 (11) | 0.0028 (9) | −0.0070 (8) | 0.0013 (9) |
N2 | 0.0403 (11) | 0.0409 (11) | 0.0392 (11) | −0.0002 (9) | −0.0037 (9) | 0.0017 (9) |
N3 | 0.0384 (11) | 0.0518 (13) | 0.0415 (12) | −0.0029 (10) | −0.0015 (9) | −0.0045 (10) |
C1 | 0.0363 (13) | 0.0466 (14) | 0.0337 (13) | 0.0015 (11) | 0.0003 (10) | −0.0014 (11) |
C2 | 0.0352 (12) | 0.0348 (12) | 0.0309 (12) | 0.0020 (10) | 0.0043 (9) | 0.0014 (11) |
C3 | 0.0451 (14) | 0.0521 (16) | 0.0453 (14) | 0.0081 (13) | −0.0073 (11) | 0.0012 (12) |
C4 | 0.0483 (15) | 0.0347 (14) | 0.0447 (15) | 0.0012 (11) | −0.0034 (11) | −0.0006 (11) |
C5 | 0.0309 (12) | 0.0385 (13) | 0.0344 (12) | 0.0012 (10) | 0.0046 (10) | −0.0016 (10) |
C6 | 0.0410 (13) | 0.0406 (14) | 0.0436 (14) | 0.0027 (11) | −0.0010 (11) | 0.0056 (11) |
C7 | 0.0457 (15) | 0.0423 (15) | 0.0507 (16) | −0.0054 (11) | 0.0019 (12) | −0.0015 (11) |
Geometric parameters (Å, º) top
S1—C1 | 1.642 (2) | C2—C5 | 1.458 (3) |
O1—C2 | 1.371 (2) | C3—C4 | 1.378 (3) |
O1—C1 | 1.379 (3) | C3—H3 | 0.9300 |
N1—C1 | 1.328 (3) | C4—C5 | 1.379 (3) |
N1—N2 | 1.373 (2) | C4—H4 | 0.9300 |
N1—H1 | 0.8600 | C5—C6 | 1.388 (3) |
N2—C2 | 1.278 (3) | C6—C7 | 1.380 (3) |
N3—C7 | 1.325 (3) | C6—H6 | 0.9300 |
N3—C3 | 1.330 (3) | C7—H7 | 0.9300 |
| | | |
C2—O1—C1 | 105.59 (16) | C4—C3—H3 | 118.4 |
C1—N1—N2 | 112.78 (18) | C3—C4—C5 | 119.0 (2) |
C1—N1—H1 | 123.6 | C3—C4—H4 | 120.5 |
N2—N1—H1 | 123.6 | C5—C4—H4 | 120.5 |
C2—N2—N1 | 103.71 (18) | C4—C5—C6 | 118.4 (2) |
C7—N3—C3 | 117.5 (2) | C4—C5—C2 | 121.4 (2) |
N1—C1—O1 | 104.75 (19) | C6—C5—C2 | 120.20 (19) |
N1—C1—S1 | 130.91 (17) | C7—C6—C5 | 118.2 (2) |
O1—C1—S1 | 124.33 (17) | C7—C6—H6 | 120.9 |
N2—C2—O1 | 113.16 (18) | C5—C6—H6 | 120.9 |
N2—C2—C5 | 128.0 (2) | N3—C7—C6 | 123.7 (2) |
O1—C2—C5 | 118.84 (18) | N3—C7—H7 | 118.1 |
N3—C3—C4 | 123.1 (2) | C6—C7—H7 | 118.1 |
N3—C3—H3 | 118.4 | | |
| | | |
C1—N1—N2—C2 | 0.1 (3) | C3—C4—C5—C6 | −0.3 (3) |
N2—N1—C1—O1 | 0.2 (2) | C3—C4—C5—C2 | 178.7 (2) |
N2—N1—C1—S1 | −179.75 (18) | N2—C2—C5—C4 | 173.3 (2) |
C2—O1—C1—N1 | −0.4 (2) | O1—C2—C5—C4 | −7.1 (3) |
C2—O1—C1—S1 | 179.54 (16) | N2—C2—C5—C6 | −7.7 (4) |
N1—N2—C2—O1 | −0.4 (2) | O1—C2—C5—C6 | 171.9 (2) |
N1—N2—C2—C5 | 179.2 (2) | C4—C5—C6—C7 | 0.5 (3) |
C1—O1—C2—N2 | 0.5 (2) | C2—C5—C6—C7 | −178.6 (2) |
C1—O1—C2—C5 | −179.15 (18) | C3—N3—C7—C6 | −0.6 (4) |
C7—N3—C3—C4 | 0.7 (4) | C5—C6—C7—N3 | 0.0 (4) |
N3—C3—C4—C5 | −0.3 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N3i | 0.86 | 1.88 | 2.737 (3) | 177 |
Symmetry code: (i) x−3/2, −y+3/2, z−1/2. |
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