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The mol­ecule of the title compound, C6H4N2O2S, is planar. An intermolecular N—H...S hydrogen bond is formed between the oxa­diazo­le group and the S atom of a neighbouring mol­ecule; the pair of mol­ecules involve a twofold screw axis along the [001] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001977/wn6214sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001977/wn6214Isup2.hkl
Contains datablock I

CCDC reference: 236057

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.030
  • wR factor = 0.107
  • Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C1 = 6.84 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: EVALCCD (Duisenberg, 1998); data reduction: EVALCCD; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

5-Furan-2-yl-1,3,4-oxadiazole-2(3H)-thione top
Crystal data top
C6H4N2O2SF(000) = 344
Mr = 168.18Dx = 1.585 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 145 reflections
a = 5.194 (5) Åθ = 6–20°
b = 20.102 (5) ŵ = 0.40 mm1
c = 6.914 (5) ÅT = 100 K
β = 102.573 (5)°Block, pale yellow
V = 704.6 (9) Å30.33 × 0.28 × 0.19 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
1855 independent reflections
Radiation source: fine-focus sealed tube1618 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 9 pixels mm-1θmax = 29.0°, θmin = 3.6°
φ and ω–scans (per frame) with 1.6° and 32 sec per frameh = 67
Absorption correction: empirical (using intensity measurements)
(SADABS, Sheldrick, 1996)
k = 2727
Tmin = 0.879, Tmax = 0.928l = 99
15534 measured reflections
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.08P)2]
where P = (Fo2 + 2Fc2)/3
1855 reflections(Δ/σ)max = 0.001
100 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.29 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S10.12856 (6)0.47180 (1)0.27058 (5)0.0173 (1)
O10.25400 (16)0.34259 (4)0.30831 (13)0.0127 (3)
O20.67037 (18)0.19945 (5)0.47082 (13)0.0169 (3)
N10.5789 (2)0.40572 (5)0.44103 (15)0.0144 (3)
N20.6744 (2)0.34169 (5)0.47497 (16)0.0155 (3)
C10.3276 (3)0.40781 (6)0.34354 (18)0.0128 (3)
C20.4738 (2)0.30573 (6)0.39286 (17)0.0120 (3)
C30.4506 (2)0.23451 (6)0.38206 (18)0.0123 (3)
C40.2480 (3)0.19344 (6)0.30458 (18)0.0157 (4)
C50.3477 (3)0.12750 (7)0.3467 (2)0.0202 (4)
C60.6001 (3)0.13386 (7)0.44587 (19)0.0203 (4)
H10.671900.440600.478900.0170*
H40.079200.205600.237900.0190*
H50.256100.088000.312400.0240*
H60.711900.098400.491300.0240*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0166 (2)0.0118 (2)0.0205 (2)0.0012 (1)0.0022 (1)0.0010 (1)
O10.0122 (5)0.0111 (4)0.0138 (4)0.0003 (3)0.0009 (3)0.0003 (3)
O20.0170 (5)0.0156 (5)0.0166 (5)0.0045 (4)0.0005 (4)0.0007 (3)
N10.0127 (5)0.0115 (5)0.0177 (5)0.0017 (4)0.0005 (4)0.0008 (4)
N20.0147 (5)0.0131 (5)0.0178 (6)0.0010 (4)0.0014 (4)0.0000 (4)
C10.0154 (6)0.0131 (6)0.0101 (6)0.0023 (5)0.0033 (4)0.0004 (4)
C20.0119 (6)0.0149 (6)0.0093 (6)0.0005 (4)0.0028 (4)0.0003 (4)
C30.0122 (6)0.0140 (6)0.0110 (6)0.0026 (4)0.0032 (5)0.0016 (4)
C40.0160 (7)0.0171 (6)0.0140 (6)0.0020 (5)0.0034 (5)0.0003 (5)
C50.0279 (7)0.0150 (6)0.0197 (7)0.0042 (5)0.0098 (6)0.0023 (5)
C60.0288 (8)0.0136 (6)0.0196 (7)0.0060 (5)0.0079 (6)0.0030 (5)
Geometric parameters (Å, º) top
S1—C11.659 (2)N1—H10.8593
O1—C11.373 (2)C2—C31.437 (2)
O1—C21.3797 (19)C3—C41.353 (2)
O2—C31.368 (2)C4—C51.430 (2)
O2—C61.369 (2)C5—C61.347 (3)
N1—N21.381 (2)C4—H40.9301
N1—C11.333 (2)C5—H50.9295
N2—C21.293 (2)C6—H60.9298
S1···N1i3.321 (3)C2···C3vi3.505 (4)
S1···H1ii3.0953C2···C4vi3.306 (4)
S1···H5iii3.0460C2···C6v3.513 (4)
S1···H1i2.5285C3···C2v3.505 (4)
S1···H6iv2.9299C3···C2vi3.600 (4)
O1···N22.236 (3)C3···C3v3.513 (4)
O1···C5v3.385 (4)C3···C3vi3.513 (4)
O2···C2vi3.296 (3)C4···N2iv3.408 (4)
O2···N22.860 (3)C4···C2v3.306 (4)
O1···H42.9073C5···O1vi3.385 (4)
N1···O12.151 (2)C5···N1v3.350 (4)
N1···S1i3.321 (3)C5···N2v3.430 (4)
N1···C5vi3.350 (4)C5···C1v3.530 (4)
N2···O12.236 (3)C5···C1vi3.531 (4)
N2···O22.860 (3)C6···N2v3.397 (4)
N2···C4vii3.408 (4)C6···C1vi3.458 (4)
N2···C5vi3.430 (4)C6···C2vi3.513 (4)
N2···C6vi3.397 (4)H1···S1viii3.0953
N2···H4vii2.6391H1···S1i2.5286
C1···C5v3.531 (4)H4···O12.9073
C1···C5vi3.530 (4)H4···N2iv2.6391
C1···C6v3.458 (4)H5···S1ix3.0460
C2···O2v3.296 (3)H6···S1vii2.9299
C2···C3v3.600 (4)
C1—O1—C2105.37 (10)O2—C3—C4111.37 (11)
C3—O2—C6105.43 (10)C2—C3—C4132.65 (11)
N2—N1—C1113.03 (10)O2—C3—C2115.95 (10)
N1—N2—C2102.77 (10)C3—C4—C5105.61 (12)
C1—N1—H1123.50C4—C5—C6106.56 (13)
N2—N1—H1123.46O2—C6—C5111.03 (12)
S1—C1—N1130.93 (10)C3—C4—H4127.15
S1—C1—O1123.77 (11)C5—C4—H4127.24
O1—C1—N1105.30 (10)C4—C5—H5126.69
O1—C2—C3117.43 (10)C6—C5—H5126.76
O1—C2—N2113.52 (10)O2—C6—H6124.47
N2—C2—C3129.04 (11)C5—C6—H6124.50
C1—O1—C2—C3178.58 (10)N1—N2—C2—C3179.00 (12)
C2—O1—C1—S1179.76 (10)N1—N2—C2—O10.17 (13)
C2—O1—C1—N10.81 (12)O1—C2—C3—C40.9 (2)
C1—O1—C2—N20.40 (13)O1—C2—C3—O2178.71 (10)
C6—O2—C3—C40.32 (14)N2—C2—C3—O20.08 (19)
C3—O2—C6—C50.21 (14)N2—C2—C3—C4177.91 (14)
C6—O2—C3—C2178.61 (10)C2—C3—C4—C5178.21 (13)
N2—N1—C1—S1179.64 (10)O2—C3—C4—C50.31 (14)
C1—N1—N2—C20.73 (13)C3—C4—C5—C60.17 (15)
N2—N1—C1—O10.98 (14)C4—C5—C6—O20.03 (17)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y, z; (iii) x, y+1/2, z+1/2; (iv) x1, y+1/2, z1/2; (v) x, y+1/2, z1/2; (vi) x, y+1/2, z+1/2; (vii) x+1, y+1/2, z+1/2; (viii) x+1, y, z; (ix) x, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S1i0.862.533.321 (3)154
Symmetry code: (i) x+1, y+1, z+1.
 

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