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The crystal structure of the title compound, C9H6OS, also known as 2-thiocoumarin, has been determined. The molecule is essentially planar and crystals may display second harmonic generation (SHG) effects.
Supporting information
CCDC reference: 177208
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.013 Å
- R factor = 0.054
- wR factor = 0.185
- Data-to-parameter ratio = 8.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 24.97
From the CIF: _reflns_number_total 815
Count of symmetry unique reflns 815
Completeness (_total/calc) 100.00%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present yes
WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 1990).
Crystal data top
C9H6OS | Dx = 1.431 Mg m−3 |
Mr = 162.21 | Melting point: 371 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 4.126 (1) Å | θ = 6.1–13.3° |
b = 17.779 (3) Å | µ = 0.36 mm−1 |
c = 10.268 (3) Å | T = 293 K |
V = 753.2 (3) Å3 | Needle, yellow |
Z = 4 | 0.38 × 0.05 × 0.04 mm |
F(000) = 336 | |
Data collection top
Enraf-Nonius Turbo-CAD-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.3° |
Graphite monochromator | h = 0→4 |
non–profiled ω/2θ scans | k = 0→21 |
815 measured reflections | l = 0→12 |
815 independent reflections | 3 standard reflections every 60 min |
375 reflections with I > 2σ(I) | intensity decay: 3% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.186 | w = 1/[σ2(Fo2) + (0.1169P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.84 | (Δ/σ)max < 0.001 |
815 reflections | Δρmax = 0.20 e Å−3 |
100 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.1 (5) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 1.2593 (9) | −0.08497 (13) | 0.6906 (2) | 0.0613 (9) | |
O1 | 0.9875 (18) | 0.0385 (3) | 0.7619 (5) | 0.0467 (17) | |
C1 | 1.072 (2) | −0.0063 (5) | 0.6592 (7) | 0.039 (2) | |
C9 | 0.695 (3) | 0.1257 (4) | 0.6242 (8) | 0.045 (3) | |
C8 | 0.803 (3) | 0.1030 (4) | 0.7458 (8) | 0.045 (3) | |
C2 | 0.976 (3) | 0.0190 (4) | 0.5324 (7) | 0.048 (3) | |
H2 | 1.0401 | −0.0083 | 0.4597 | 0.057* | |
C4 | 0.513 (3) | 0.1906 (4) | 0.6149 (10) | 0.055 (3) | |
H4 | 0.4342 | 0.2066 | 0.5347 | 0.066* | |
C7 | 0.743 (3) | 0.1440 (4) | 0.8571 (8) | 0.050 (2) | |
H7 | 0.8250 | 0.1289 | 0.9373 | 0.060* | |
C3 | 0.795 (3) | 0.0807 (4) | 0.5158 (7) | 0.046 (2) | |
H3 | 0.7339 | 0.0948 | 0.4321 | 0.056* | |
C6 | 0.555 (3) | 0.2086 (5) | 0.8456 (8) | 0.059 (3) | |
H6 | 0.5016 | 0.2364 | 0.9193 | 0.070* | |
C5 | 0.449 (3) | 0.2312 (5) | 0.7258 (10) | 0.064 (3) | |
H5 | 0.3294 | 0.2754 | 0.7191 | 0.076* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0697 (19) | 0.0619 (14) | 0.0521 (12) | 0.014 (2) | −0.002 (2) | 0.0013 (12) |
O1 | 0.057 (4) | 0.051 (3) | 0.032 (3) | −0.007 (4) | −0.004 (4) | 0.003 (3) |
C1 | 0.025 (6) | 0.053 (5) | 0.038 (4) | −0.018 (5) | −0.007 (4) | −0.007 (4) |
C9 | 0.049 (8) | 0.038 (4) | 0.048 (5) | −0.014 (6) | −0.004 (6) | 0.008 (4) |
C8 | 0.043 (7) | 0.045 (5) | 0.046 (4) | −0.004 (6) | 0.002 (6) | 0.000 (4) |
C2 | 0.058 (7) | 0.049 (5) | 0.036 (5) | −0.007 (6) | −0.006 (6) | 0.000 (4) |
C4 | 0.046 (7) | 0.055 (6) | 0.064 (6) | −0.009 (6) | −0.010 (7) | 0.014 (5) |
C7 | 0.052 (7) | 0.046 (4) | 0.052 (5) | −0.001 (7) | −0.002 (8) | −0.003 (4) |
C3 | 0.045 (7) | 0.061 (5) | 0.034 (4) | −0.006 (7) | −0.010 (6) | 0.011 (4) |
C6 | 0.059 (8) | 0.064 (6) | 0.053 (6) | −0.007 (7) | 0.008 (6) | −0.013 (5) |
C5 | 0.063 (8) | 0.043 (6) | 0.085 (8) | −0.006 (6) | 0.012 (8) | −0.006 (5) |
Geometric parameters (Å, º) top
S1—C1 | 1.630 (9) | C2—H2 | 0.930 |
O1—C1 | 1.367 (10) | C4—C5 | 1.373 (13) |
O1—C8 | 1.388 (10) | C4—H4 | 0.930 |
C1—C2 | 1.434 (10) | C7—C6 | 1.391 (14) |
C9—C8 | 1.385 (12) | C7—H7 | 0.930 |
C9—C4 | 1.382 (12) | C3—H3 | 0.930 |
C9—C3 | 1.431 (11) | C6—C5 | 1.366 (13) |
C8—C7 | 1.378 (11) | C6—H6 | 0.930 |
C2—C3 | 1.337 (12) | C5—H5 | 0.930 |
| | | |
C1—O1—C8 | 122.0 (6) | C5—C4—H4 | 120.5 |
O1—C1—C2 | 116.6 (8) | C9—C4—H4 | 120.5 |
O1—C1—S1 | 117.9 (6) | C8—C7—C6 | 117.8 (8) |
C2—C1—S1 | 125.5 (7) | C8—C7—H7 | 121.1 |
C8—C9—C4 | 118.7 (9) | C6—C7—H7 | 121.1 |
C8—C9—C3 | 116.5 (8) | C2—C3—C9 | 121.3 (7) |
C4—C9—C3 | 124.8 (9) | C2—C3—H3 | 119.3 |
O1—C8—C9 | 121.6 (8) | C9—C3—H3 | 119.3 |
O1—C8—C7 | 115.9 (8) | C5—C6—C7 | 119.8 (9) |
C9—C8—C7 | 122.5 (8) | C5—C6—H6 | 120.1 |
C3—C2—C1 | 121.9 (8) | C7—C6—H6 | 120.1 |
C3—C2—H2 | 119.1 | C6—C5—C4 | 122.1 (10) |
C1—C2—H2 | 119.1 | C6—C5—H5 | 119.0 |
C5—C4—C9 | 119.1 (10) | C4—C5—H5 | 119.0 |
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