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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801019067/cf6115sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801019067/cf6115Isup2.hkl
Contains datablock I

CCDC reference: 177208

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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).

2H-chromene-2-thione top
Crystal data top
C9H6OSDx = 1.431 Mg m3
Mr = 162.21Melting point: 371 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 4.126 (1) Åθ = 6.1–13.3°
b = 17.779 (3) ŵ = 0.36 mm1
c = 10.268 (3) ÅT = 293 K
V = 753.2 (3) Å3Needle, yellow
Z = 40.38 × 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 tubeθmax = 25.0°, θmin = 2.3°
Graphite monochromatorh = 04
non–profiled ω/2θ scansk = 021
815 measured reflectionsl = 012
815 independent reflections3 standard reflections every 60 min
375 reflections with I > 2σ(I) intensity decay: 3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-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 reflectionsΔρmax = 0.20 e Å3
100 parametersΔρmin = 0.26 e Å3
0 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute 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
xyzUiso*/Ueq
S11.2593 (9)0.08497 (13)0.6906 (2)0.0613 (9)
O10.9875 (18)0.0385 (3)0.7619 (5)0.0467 (17)
C11.072 (2)0.0063 (5)0.6592 (7)0.039 (2)
C90.695 (3)0.1257 (4)0.6242 (8)0.045 (3)
C80.803 (3)0.1030 (4)0.7458 (8)0.045 (3)
C20.976 (3)0.0190 (4)0.5324 (7)0.048 (3)
H21.04010.00830.45970.057*
C40.513 (3)0.1906 (4)0.6149 (10)0.055 (3)
H40.43420.20660.53470.066*
C70.743 (3)0.1440 (4)0.8571 (8)0.050 (2)
H70.82500.12890.93730.060*
C30.795 (3)0.0807 (4)0.5158 (7)0.046 (2)
H30.73390.09480.43210.056*
C60.555 (3)0.2086 (5)0.8456 (8)0.059 (3)
H60.50160.23640.91930.070*
C50.449 (3)0.2312 (5)0.7258 (10)0.064 (3)
H50.32940.27540.71910.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0697 (19)0.0619 (14)0.0521 (12)0.014 (2)0.002 (2)0.0013 (12)
O10.057 (4)0.051 (3)0.032 (3)0.007 (4)0.004 (4)0.003 (3)
C10.025 (6)0.053 (5)0.038 (4)0.018 (5)0.007 (4)0.007 (4)
C90.049 (8)0.038 (4)0.048 (5)0.014 (6)0.004 (6)0.008 (4)
C80.043 (7)0.045 (5)0.046 (4)0.004 (6)0.002 (6)0.000 (4)
C20.058 (7)0.049 (5)0.036 (5)0.007 (6)0.006 (6)0.000 (4)
C40.046 (7)0.055 (6)0.064 (6)0.009 (6)0.010 (7)0.014 (5)
C70.052 (7)0.046 (4)0.052 (5)0.001 (7)0.002 (8)0.003 (4)
C30.045 (7)0.061 (5)0.034 (4)0.006 (7)0.010 (6)0.011 (4)
C60.059 (8)0.064 (6)0.053 (6)0.007 (7)0.008 (6)0.013 (5)
C50.063 (8)0.043 (6)0.085 (8)0.006 (6)0.012 (8)0.006 (5)
Geometric parameters (Å, º) top
S1—C11.630 (9)C2—H20.930
O1—C11.367 (10)C4—C51.373 (13)
O1—C81.388 (10)C4—H40.930
C1—C21.434 (10)C7—C61.391 (14)
C9—C81.385 (12)C7—H70.930
C9—C41.382 (12)C3—H30.930
C9—C31.431 (11)C6—C51.366 (13)
C8—C71.378 (11)C6—H60.930
C2—C31.337 (12)C5—H50.930
C1—O1—C8122.0 (6)C5—C4—H4120.5
O1—C1—C2116.6 (8)C9—C4—H4120.5
O1—C1—S1117.9 (6)C8—C7—C6117.8 (8)
C2—C1—S1125.5 (7)C8—C7—H7121.1
C8—C9—C4118.7 (9)C6—C7—H7121.1
C8—C9—C3116.5 (8)C2—C3—C9121.3 (7)
C4—C9—C3124.8 (9)C2—C3—H3119.3
O1—C8—C9121.6 (8)C9—C3—H3119.3
O1—C8—C7115.9 (8)C5—C6—C7119.8 (9)
C9—C8—C7122.5 (8)C5—C6—H6120.1
C3—C2—C1121.9 (8)C7—C6—H6120.1
C3—C2—H2119.1C6—C5—C4122.1 (10)
C1—C2—H2119.1C6—C5—H5119.0
C5—C4—C9119.1 (10)C4—C5—H5119.0
 

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