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In the title compound, C8H6N2OS, the planar oxadiazole ring is effectively coplanar with the phenyl ring. This facilitates the formation of N—H...S inter­actions, leading to a thione tautomer in the solid state, and the formation of centrosymmetric dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806052238/kj2029sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806052238/kj2029Isup2.hkl
Contains datablock I

CCDC reference: 636720

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.106
  • Data-to-parameter ratio = 26.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT021_ALERT_1_B Ratio Unique / Expected Reflections too High ... 1.13
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.79 mm PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

5-Phenyl-1,3,4-oxadiazole-2(3H)-thione top
Crystal data top
C8H6N2OSF(000) = 368
Mr = 178.21Dx = 1.440 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.3414 (15) ÅCell parameters from 3166 reflections
b = 4.6589 (16) Åθ = 3.7–30.6°
c = 16.0242 (7) ŵ = 0.34 mm1
β = 103.845 (5)°T = 298 K
V = 822.1 (3) Å3Plate, colourless
Z = 40.79 × 0.23 × 0.07 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2888 independent reflections
Radiation source: fine-focus sealed tube2386 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 30.7°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.775, Tmax = 0.977k = 66
12966 measured reflectionsl = 2222
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0696P)2]
where P = (Fo2 + 2Fc2)/3
2888 reflections(Δ/σ)max = 0.001
110 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

Experimental. IR (Medium?, ν, cm-1): 3108 (–NH), 1610 (CN), 1145 (–CS); 1H NMR (DMSO-d6, TMS, δ, p.p.m.): 13.56 (s, 1H, NH), 8.55–7.25 (m, 5H, phenyl); 13C NMR (DMSO-d6, TMS, δ, p.p.m.): 131.48 (C1), 128.68 (C2, C6),125.29 (C3, C5), 121.73 (C4), 159.72 (C7), 176.74 (C8). The IR and NMR data confirm the presence of the thione tautomer in the solid state as well as in solution.

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
S10.68387 (3)1.03196 (9)0.45854 (2)0.04557 (13)
O10.60441 (7)0.6440 (2)0.33504 (6)0.0379 (2)
C10.49558 (11)0.2792 (3)0.23604 (8)0.0372 (3)
C70.50227 (11)0.4791 (3)0.30667 (9)0.0374 (3)
C80.58430 (11)0.8025 (3)0.40210 (8)0.0375 (3)
N10.42105 (12)0.5232 (3)0.34905 (9)0.0477 (3)
C60.59515 (12)0.2282 (4)0.20132 (10)0.0454 (3)
H6A0.66780.32520.22260.055*
N20.47371 (10)0.7277 (3)0.40827 (8)0.0475 (3)
H2B0.43860.79960.44550.057*
C50.58552 (15)0.0333 (4)0.13530 (10)0.0531 (4)
H5A0.65210.00370.11260.064*
C20.38610 (12)0.1370 (4)0.20291 (10)0.0470 (3)
H2A0.31930.17140.22570.056*
C40.47638 (15)0.1079 (4)0.10273 (10)0.0544 (4)
H4A0.47020.23890.05810.065*
C30.37748 (16)0.0554 (4)0.13593 (11)0.0536 (4)
H3A0.30450.14960.11330.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.04042 (19)0.0496 (2)0.0479 (2)0.00313 (15)0.01284 (15)0.00394 (16)
O10.0333 (4)0.0403 (5)0.0424 (5)0.0001 (4)0.0134 (4)0.0003 (4)
C10.0347 (6)0.0375 (7)0.0395 (6)0.0024 (5)0.0092 (5)0.0031 (5)
C70.0303 (5)0.0392 (7)0.0431 (6)0.0015 (5)0.0093 (5)0.0041 (6)
C80.0378 (6)0.0369 (7)0.0396 (6)0.0051 (5)0.0125 (5)0.0047 (5)
N10.0366 (6)0.0552 (8)0.0547 (7)0.0038 (5)0.0174 (5)0.0099 (6)
C60.0361 (6)0.0533 (9)0.0487 (7)0.0028 (6)0.0136 (6)0.0039 (6)
N20.0400 (6)0.0553 (8)0.0522 (7)0.0027 (6)0.0211 (5)0.0110 (6)
C50.0478 (8)0.0624 (11)0.0543 (9)0.0004 (7)0.0227 (7)0.0050 (8)
C20.0351 (6)0.0533 (9)0.0538 (8)0.0028 (6)0.0130 (6)0.0025 (7)
C40.0616 (10)0.0552 (10)0.0466 (8)0.0018 (8)0.0131 (7)0.0085 (7)
C30.0478 (8)0.0555 (10)0.0546 (9)0.0086 (7)0.0069 (7)0.0066 (7)
Geometric parameters (Å, º) top
S1—C81.6574 (15)C6—H6A0.9300
O1—C81.3672 (16)N2—H2B0.8600
O1—C71.3739 (16)C5—C41.389 (2)
C1—C61.3936 (19)C5—H5A0.9300
C1—C21.3953 (19)C2—C31.384 (2)
C1—C71.454 (2)C2—H2A0.9300
C7—N11.2850 (19)C4—C31.373 (2)
C8—N21.3281 (17)C4—H4A0.9300
N1—N21.3761 (18)C3—H3A0.9300
C6—C51.378 (2)
C8—O1—C7106.03 (10)C8—N2—H2B123.5
C6—C1—C2119.97 (14)N1—N2—H2B123.5
C6—C1—C7121.59 (12)C6—C5—C4120.02 (15)
C2—C1—C7118.44 (12)C6—C5—H5A120.0
N1—C7—O1112.96 (12)C4—C5—H5A120.0
N1—C7—C1127.12 (13)C3—C2—C1119.60 (14)
O1—C7—C1119.92 (12)C3—C2—H2A120.2
N2—C8—O1104.77 (12)C1—C2—H2A120.2
N2—C8—S1131.38 (12)C3—C4—C5120.48 (15)
O1—C8—S1123.86 (10)C3—C4—H4A119.8
C7—N1—N2103.14 (12)C5—C4—H4A119.8
C5—C6—C1119.71 (14)C4—C3—C2120.20 (15)
C5—C6—H6A120.1C4—C3—H3A119.9
C1—C6—H6A120.1C2—C3—H3A119.9
C8—N2—N1113.09 (12)
C8—O1—C7—N10.75 (15)C7—C1—C6—C5178.92 (14)
C8—O1—C7—C1178.73 (11)O1—C8—N2—N11.02 (17)
C6—C1—C7—N1172.88 (15)S1—C8—N2—N1179.02 (12)
C2—C1—C7—N17.2 (2)C7—N1—N2—C80.58 (18)
C6—C1—C7—O16.5 (2)C1—C6—C5—C41.0 (3)
C2—C1—C7—O1173.42 (13)C6—C1—C2—C30.4 (2)
C7—O1—C8—N21.02 (14)C7—C1—C2—C3179.69 (14)
C7—O1—C8—S1179.01 (10)C6—C5—C4—C30.1 (3)
O1—C7—N1—N20.13 (16)C5—C4—C3—C20.6 (3)
C1—C7—N1—N2179.30 (13)C1—C2—C3—C40.5 (3)
C2—C1—C6—C51.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···S1i0.862.443.2907 (13)173
Symmetry code: (i) x+1, y+2, z+1.
 

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