The molecule of the title compound, C
6H
4N
2O
2S, 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
CCDC reference: 236057
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (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
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(3
H)-thione
top
Crystal data top
C6H4N2O2S | F(000) = 344 |
Mr = 168.18 | Dx = 1.585 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 145 reflections |
a = 5.194 (5) Å | θ = 6–20° |
b = 20.102 (5) Å | µ = 0.40 mm−1 |
c = 6.914 (5) Å | T = 100 K |
β = 102.573 (5)° | Block, pale yellow |
V = 704.6 (9) Å3 | 0.33 × 0.28 × 0.19 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 1855 independent reflections |
Radiation source: fine-focus sealed tube | 1618 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 9 pixels mm-1 | θmax = 29.0°, θmin = 3.6° |
φ and ω–scans (per frame) with 1.6° and 32 sec per frame | h = −6→7 |
Absorption correction: empirical (using intensity measurements) (SADABS, Sheldrick, 1996) | k = −27→27 |
Tmin = 0.879, Tmax = 0.928 | l = −9→9 |
15534 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-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 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.12856 (6) | 0.47180 (1) | 0.27058 (5) | 0.0173 (1) | |
O1 | 0.25400 (16) | 0.34259 (4) | 0.30831 (13) | 0.0127 (3) | |
O2 | 0.67037 (18) | 0.19945 (5) | 0.47082 (13) | 0.0169 (3) | |
N1 | 0.5789 (2) | 0.40572 (5) | 0.44103 (15) | 0.0144 (3) | |
N2 | 0.6744 (2) | 0.34169 (5) | 0.47497 (16) | 0.0155 (3) | |
C1 | 0.3276 (3) | 0.40781 (6) | 0.34354 (18) | 0.0128 (3) | |
C2 | 0.4738 (2) | 0.30573 (6) | 0.39286 (17) | 0.0120 (3) | |
C3 | 0.4506 (2) | 0.23451 (6) | 0.38206 (18) | 0.0123 (3) | |
C4 | 0.2480 (3) | 0.19344 (6) | 0.30458 (18) | 0.0157 (4) | |
C5 | 0.3477 (3) | 0.12750 (7) | 0.3467 (2) | 0.0202 (4) | |
C6 | 0.6001 (3) | 0.13386 (7) | 0.44587 (19) | 0.0203 (4) | |
H1 | 0.67190 | 0.44060 | 0.47890 | 0.0170* | |
H4 | 0.07920 | 0.20560 | 0.23790 | 0.0190* | |
H5 | 0.25610 | 0.08800 | 0.31240 | 0.0240* | |
H6 | 0.71190 | 0.09840 | 0.49130 | 0.0240* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0166 (2) | 0.0118 (2) | 0.0205 (2) | 0.0012 (1) | −0.0022 (1) | −0.0010 (1) |
O1 | 0.0122 (5) | 0.0111 (4) | 0.0138 (4) | 0.0003 (3) | 0.0009 (3) | −0.0003 (3) |
O2 | 0.0170 (5) | 0.0156 (5) | 0.0166 (5) | 0.0045 (4) | 0.0005 (4) | 0.0007 (3) |
N1 | 0.0127 (5) | 0.0115 (5) | 0.0177 (5) | −0.0017 (4) | 0.0005 (4) | −0.0008 (4) |
N2 | 0.0147 (5) | 0.0131 (5) | 0.0178 (6) | 0.0010 (4) | 0.0014 (4) | 0.0000 (4) |
C1 | 0.0154 (6) | 0.0131 (6) | 0.0101 (6) | −0.0023 (5) | 0.0033 (4) | −0.0004 (4) |
C2 | 0.0119 (6) | 0.0149 (6) | 0.0093 (6) | 0.0005 (4) | 0.0028 (4) | 0.0003 (4) |
C3 | 0.0122 (6) | 0.0140 (6) | 0.0110 (6) | 0.0026 (4) | 0.0032 (5) | 0.0016 (4) |
C4 | 0.0160 (7) | 0.0171 (6) | 0.0140 (6) | −0.0020 (5) | 0.0034 (5) | −0.0003 (5) |
C5 | 0.0279 (7) | 0.0150 (6) | 0.0197 (7) | −0.0042 (5) | 0.0098 (6) | −0.0023 (5) |
C6 | 0.0288 (8) | 0.0136 (6) | 0.0196 (7) | 0.0060 (5) | 0.0079 (6) | 0.0030 (5) |
Geometric parameters (Å, º) top
S1—C1 | 1.659 (2) | N1—H1 | 0.8593 |
O1—C1 | 1.373 (2) | C2—C3 | 1.437 (2) |
O1—C2 | 1.3797 (19) | C3—C4 | 1.353 (2) |
O2—C3 | 1.368 (2) | C4—C5 | 1.430 (2) |
O2—C6 | 1.369 (2) | C5—C6 | 1.347 (3) |
N1—N2 | 1.381 (2) | C4—H4 | 0.9301 |
N1—C1 | 1.333 (2) | C5—H5 | 0.9295 |
N2—C2 | 1.293 (2) | C6—H6 | 0.9298 |
| | | |
S1···N1i | 3.321 (3) | C2···C3vi | 3.505 (4) |
S1···H1ii | 3.0953 | C2···C4vi | 3.306 (4) |
S1···H5iii | 3.0460 | C2···C6v | 3.513 (4) |
S1···H1i | 2.5285 | C3···C2v | 3.505 (4) |
S1···H6iv | 2.9299 | C3···C2vi | 3.600 (4) |
O1···N2 | 2.236 (3) | C3···C3v | 3.513 (4) |
O1···C5v | 3.385 (4) | C3···C3vi | 3.513 (4) |
O2···C2vi | 3.296 (3) | C4···N2iv | 3.408 (4) |
O2···N2 | 2.860 (3) | C4···C2v | 3.306 (4) |
O1···H4 | 2.9073 | C5···O1vi | 3.385 (4) |
N1···O1 | 2.151 (2) | C5···N1v | 3.350 (4) |
N1···S1i | 3.321 (3) | C5···N2v | 3.430 (4) |
N1···C5vi | 3.350 (4) | C5···C1v | 3.530 (4) |
N2···O1 | 2.236 (3) | C5···C1vi | 3.531 (4) |
N2···O2 | 2.860 (3) | C6···N2v | 3.397 (4) |
N2···C4vii | 3.408 (4) | C6···C1vi | 3.458 (4) |
N2···C5vi | 3.430 (4) | C6···C2vi | 3.513 (4) |
N2···C6vi | 3.397 (4) | H1···S1viii | 3.0953 |
N2···H4vii | 2.6391 | H1···S1i | 2.5286 |
C1···C5v | 3.531 (4) | H4···O1 | 2.9073 |
C1···C5vi | 3.530 (4) | H4···N2iv | 2.6391 |
C1···C6v | 3.458 (4) | H5···S1ix | 3.0460 |
C2···O2v | 3.296 (3) | H6···S1vii | 2.9299 |
C2···C3v | 3.600 (4) | | |
| | | |
C1—O1—C2 | 105.37 (10) | O2—C3—C4 | 111.37 (11) |
C3—O2—C6 | 105.43 (10) | C2—C3—C4 | 132.65 (11) |
N2—N1—C1 | 113.03 (10) | O2—C3—C2 | 115.95 (10) |
N1—N2—C2 | 102.77 (10) | C3—C4—C5 | 105.61 (12) |
C1—N1—H1 | 123.50 | C4—C5—C6 | 106.56 (13) |
N2—N1—H1 | 123.46 | O2—C6—C5 | 111.03 (12) |
S1—C1—N1 | 130.93 (10) | C3—C4—H4 | 127.15 |
S1—C1—O1 | 123.77 (11) | C5—C4—H4 | 127.24 |
O1—C1—N1 | 105.30 (10) | C4—C5—H5 | 126.69 |
O1—C2—C3 | 117.43 (10) | C6—C5—H5 | 126.76 |
O1—C2—N2 | 113.52 (10) | O2—C6—H6 | 124.47 |
N2—C2—C3 | 129.04 (11) | C5—C6—H6 | 124.50 |
| | | |
C1—O1—C2—C3 | 178.58 (10) | N1—N2—C2—C3 | −179.00 (12) |
C2—O1—C1—S1 | −179.76 (10) | N1—N2—C2—O1 | −0.17 (13) |
C2—O1—C1—N1 | 0.81 (12) | O1—C2—C3—C4 | −0.9 (2) |
C1—O1—C2—N2 | −0.40 (13) | O1—C2—C3—O2 | −178.71 (10) |
C6—O2—C3—C4 | 0.32 (14) | N2—C2—C3—O2 | 0.08 (19) |
C3—O2—C6—C5 | −0.21 (14) | N2—C2—C3—C4 | 177.91 (14) |
C6—O2—C3—C2 | 178.61 (10) | C2—C3—C4—C5 | −178.21 (13) |
N2—N1—C1—S1 | 179.64 (10) | O2—C3—C4—C5 | −0.31 (14) |
C1—N1—N2—C2 | 0.73 (13) | C3—C4—C5—C6 | 0.17 (15) |
N2—N1—C1—O1 | −0.98 (14) | C4—C5—C6—O2 | 0.03 (17) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) −x, y+1/2, −z+1/2; (iv) x−1, −y+1/2, z−1/2; (v) x, −y+1/2, z−1/2; (vi) x, −y+1/2, z+1/2; (vii) x+1, −y+1/2, z+1/2; (viii) x+1, y, z; (ix) −x, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S1i | 0.86 | 2.53 | 3.321 (3) | 154 |
Symmetry code: (i) −x+1, −y+1, −z+1. |