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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047374/lh2230sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047374/lh2230Isup2.hkl
Contains datablock I

CCDC reference: 630055

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

No syntax errors found



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

Computing details top

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 top
Crystal data top
C7H5N3OSF(000) = 368
Mr = 179.20Dx = 1.503 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1342 reflections
a = 5.1351 (2) Åθ = 2.7–26.2°
b = 18.1940 (7) ŵ = 0.36 mm1
c = 8.5727 (4) ÅT = 293 K
β = 98.694 (3)°Plate, pale yellow
V = 791.73 (6) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
1804 independent reflections
Radiation source: fine-focus sealed tube1371 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 27.6°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 66
Tmin = 0.900, Tmax = 0.965k = 2319
4047 measured reflectionsl = 115
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098All H-atom parameters refined
S = 1.00 w = 1/[σ2(Fo2) + (0.0475P)2 + 0.162P]
where P = (Fo2 + 2Fc2)/3
1804 reflections(Δ/σ)max = 0.001
129 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.25 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. 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
S10.32792 (10)0.62705 (3)0.23934 (6)0.04673 (19)
O10.6622 (2)0.61418 (6)0.03048 (13)0.0366 (3)
N11.2852 (3)0.65454 (9)0.32830 (17)0.0405 (4)
N20.7374 (3)0.72894 (8)0.03755 (17)0.0380 (4)
N30.5637 (3)0.72662 (8)0.07103 (17)0.0389 (4)
C11.1196 (4)0.67778 (11)0.2333 (2)0.0369 (4)
C20.9621 (3)0.63049 (9)0.16110 (19)0.0333 (4)
C30.9754 (4)0.55578 (10)0.1904 (2)0.0404 (4)
C41.1448 (4)0.53137 (11)0.2893 (2)0.0460 (5)
C51.2948 (4)0.58204 (11)0.3556 (2)0.0436 (5)
C60.7898 (3)0.66080 (9)0.05733 (19)0.0332 (4)
C70.5156 (3)0.65819 (10)0.11450 (19)0.0352 (4)
H11.119 (4)0.7289 (11)0.214 (2)0.045 (5)*
H30.875 (4)0.5229 (10)0.143 (2)0.042 (5)*
H51.421 (4)0.5668 (12)0.420 (2)0.055 (6)*
H1A0.485 (4)0.7694 (13)0.105 (2)0.066 (7)*
H41.158 (4)0.4806 (12)0.312 (2)0.050 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0547 (3)0.0428 (3)0.0482 (3)0.0054 (2)0.0256 (2)0.0019 (2)
O10.0422 (7)0.0309 (6)0.0400 (7)0.0015 (5)0.0170 (5)0.0008 (5)
N10.0416 (8)0.0418 (9)0.0408 (8)0.0004 (7)0.0146 (7)0.0027 (7)
N20.0426 (9)0.0330 (8)0.0414 (8)0.0003 (7)0.0161 (7)0.0015 (6)
N30.0453 (9)0.0329 (8)0.0425 (9)0.0004 (7)0.0198 (7)0.0008 (7)
C10.0393 (10)0.0324 (9)0.0403 (10)0.0003 (8)0.0104 (8)0.0016 (8)
C20.0342 (9)0.0343 (9)0.0320 (9)0.0006 (7)0.0069 (7)0.0022 (7)
C30.0486 (11)0.0322 (9)0.0428 (10)0.0037 (9)0.0144 (9)0.0022 (8)
C40.0586 (13)0.0337 (11)0.0483 (11)0.0048 (9)0.0160 (10)0.0033 (9)
C50.0469 (11)0.0468 (12)0.0403 (10)0.0058 (9)0.0168 (9)0.0011 (8)
C60.0356 (9)0.0323 (9)0.0327 (9)0.0029 (7)0.0079 (7)0.0015 (7)
C70.0386 (9)0.0347 (9)0.0334 (9)0.0014 (8)0.0093 (7)0.0031 (7)
Geometric parameters (Å, º) top
S1—C71.6454 (17)C1—C21.389 (2)
O1—C61.3655 (19)C1—H10.945 (19)
O1—C71.375 (2)C2—C31.386 (2)
N1—C11.332 (2)C2—C61.455 (2)
N1—C51.342 (2)C3—C41.377 (3)
N2—C61.285 (2)C3—H30.924 (18)
N2—N31.384 (2)C4—C51.378 (3)
N3—C71.333 (2)C4—H40.95 (2)
N3—H1A0.94 (2)C5—H50.95 (2)
C6—O1—C7105.86 (13)C2—C3—H3120.6 (12)
C1—N1—C5117.53 (16)C3—C4—C5118.87 (18)
C6—N2—N3103.21 (14)C3—C4—H4120.8 (12)
C7—N3—N2112.44 (15)C5—C4—H4120.4 (12)
C7—N3—H1A125.4 (13)N1—C5—C4123.25 (17)
N2—N3—H1A122.1 (13)N1—C5—H5115.6 (13)
N1—C1—C2122.98 (17)C4—C5—H5121.1 (13)
N1—C1—H1116.0 (12)N2—C6—O1113.51 (14)
C2—C1—H1121.0 (12)N2—C6—C2127.24 (15)
C3—C2—C1118.63 (16)O1—C6—C2119.25 (15)
C3—C2—C6122.25 (15)N3—C7—O1104.97 (14)
C1—C2—C6119.13 (16)N3—C7—S1130.90 (14)
C4—C3—C2118.74 (17)O1—C7—S1124.13 (13)
C4—C3—H3120.7 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1A···N1i0.94 (2)1.86 (2)2.800 (2)172 (2)
Symmetry code: (i) x1, y+3/2, z+1/2.
 

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