5-(3-Pyrid­yl)-1,3,4-oxadiazole-2-thione

In the title compound, C₇H₅N₃OS, the dihedral angle between the pyridyl and oxadiazole rings is 9.32 (2) Å. In the crystal structure, a combination of inter­molecular N—H...N hydrogen bonds and π–π stacking inter­actions forms a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.098
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1999); software used to prepare material for publication: SHELXTL.

5-(3-Pyridyl)-1,3,4-oxadiazole-2-thione

Crystal data

C7H5N3OS	F(000) = 368
Mr = 179.20	Dx = 1.503 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1342 reflections
a = 5.1351 (2) Å	θ = 2.7–26.2°
b = 18.1940 (7) Å	µ = 0.36 mm^−1
c = 8.5727 (4) Å	T = 293 K
β = 98.694 (3)°	Plate, pale yellow
V = 791.73 (6) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer	1804 independent reflections
Radiation source: fine-focus sealed tube	1371 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 27.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.900, Tmax = 0.965	k = −23→19
4047 measured reflections	l = −11→5

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	All H-atom parameters refined
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0475P)^2 + 0.162P] where P = (Fo^2 + 2Fc^2)/3
1804 reflections	(Δ/σ)max = 0.001
129 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.32792 (10)	0.62705 (3)	0.23934 (6)	0.04673 (19)
O1	0.6622 (2)	0.61418 (6)	0.03048 (13)	0.0366 (3)
N1	1.2852 (3)	0.65454 (9)	−0.32830 (17)	0.0405 (4)
N2	0.7374 (3)	0.72894 (8)	−0.03755 (17)	0.0380 (4)
N3	0.5637 (3)	0.72662 (8)	0.07103 (17)	0.0389 (4)
C1	1.1196 (4)	0.67778 (11)	−0.2333 (2)	0.0369 (4)
C2	0.9621 (3)	0.63049 (9)	−0.16110 (19)	0.0333 (4)
C3	0.9754 (4)	0.55578 (10)	−0.1904 (2)	0.0404 (4)
C4	1.1448 (4)	0.53137 (11)	−0.2893 (2)	0.0460 (5)
C5	1.2948 (4)	0.58204 (11)	−0.3556 (2)	0.0436 (5)
C6	0.7898 (3)	0.66080 (9)	−0.05733 (19)	0.0332 (4)
C7	0.5156 (3)	0.65819 (10)	0.11450 (19)	0.0352 (4)
H1	1.119 (4)	0.7289 (11)	−0.214 (2)	0.045 (5)*
H3	0.875 (4)	0.5229 (10)	−0.143 (2)	0.042 (5)*
H5	1.421 (4)	0.5668 (12)	−0.420 (2)	0.055 (6)*
H1A	0.485 (4)	0.7694 (13)	0.105 (2)	0.066 (7)*
H4	1.158 (4)	0.4806 (12)	−0.312 (2)	0.050 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0547 (3)	0.0428 (3)	0.0482 (3)	−0.0054 (2)	0.0256 (2)	0.0019 (2)
O1	0.0422 (7)	0.0309 (6)	0.0400 (7)	−0.0015 (5)	0.0170 (5)	0.0008 (5)
N1	0.0416 (8)	0.0418 (9)	0.0408 (8)	0.0004 (7)	0.0146 (7)	0.0027 (7)
N2	0.0426 (9)	0.0330 (8)	0.0414 (8)	−0.0003 (7)	0.0161 (7)	0.0015 (6)
N3	0.0453 (9)	0.0329 (8)	0.0425 (9)	−0.0004 (7)	0.0198 (7)	−0.0008 (7)
C1	0.0393 (10)	0.0324 (9)	0.0403 (10)	−0.0003 (8)	0.0104 (8)	0.0016 (8)
C2	0.0342 (9)	0.0343 (9)	0.0320 (9)	0.0006 (7)	0.0069 (7)	0.0022 (7)
C3	0.0486 (11)	0.0322 (9)	0.0428 (10)	−0.0037 (9)	0.0144 (9)	0.0022 (8)
C4	0.0586 (13)	0.0337 (11)	0.0483 (11)	0.0048 (9)	0.0160 (10)	−0.0033 (9)
C5	0.0469 (11)	0.0468 (12)	0.0403 (10)	0.0058 (9)	0.0168 (9)	−0.0011 (8)
C6	0.0356 (9)	0.0323 (9)	0.0327 (9)	−0.0029 (7)	0.0079 (7)	0.0015 (7)
C7	0.0386 (9)	0.0347 (9)	0.0334 (9)	−0.0014 (8)	0.0093 (7)	−0.0031 (7)

Geometric parameters (Å, º)

S1—C7	1.6454 (17)	C1—C2	1.389 (2)
O1—C6	1.3655 (19)	C1—H1	0.945 (19)
O1—C7	1.375 (2)	C2—C3	1.386 (2)
N1—C1	1.332 (2)	C2—C6	1.455 (2)
N1—C5	1.342 (2)	C3—C4	1.377 (3)
N2—C6	1.285 (2)	C3—H3	0.924 (18)
N2—N3	1.384 (2)	C4—C5	1.378 (3)
N3—C7	1.333 (2)	C4—H4	0.95 (2)
N3—H1A	0.94 (2)	C5—H5	0.95 (2)
C6—O1—C7	105.86 (13)	C2—C3—H3	120.6 (12)
C1—N1—C5	117.53 (16)	C3—C4—C5	118.87 (18)
C6—N2—N3	103.21 (14)	C3—C4—H4	120.8 (12)
C7—N3—N2	112.44 (15)	C5—C4—H4	120.4 (12)
C7—N3—H1A	125.4 (13)	N1—C5—C4	123.25 (17)
N2—N3—H1A	122.1 (13)	N1—C5—H5	115.6 (13)
N1—C1—C2	122.98 (17)	C4—C5—H5	121.1 (13)
N1—C1—H1	116.0 (12)	N2—C6—O1	113.51 (14)
C2—C1—H1	121.0 (12)	N2—C6—C2	127.24 (15)
C3—C2—C1	118.63 (16)	O1—C6—C2	119.25 (15)
C3—C2—C6	122.25 (15)	N3—C7—O1	104.97 (14)
C1—C2—C6	119.13 (16)	N3—C7—S1	130.90 (14)
C4—C3—C2	118.74 (17)	O1—C7—S1	124.13 (13)
C4—C3—H3	120.7 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1A···N1^i	0.94 (2)	1.86 (2)	2.800 (2)	172 (2)

Symmetry code: (i) x−1, −y+3/2, z+1/2.