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The crystal structure of the title compound, C9H6OS, also known as 2H-thio­chromen-2-one, has been determined as monoclinic in the space group Pc at room temperature. The mol­ecule is essentially planar and the crystal is a candidate for second harmonic generation (SHG) effects.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802003628/cf6156sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802003628/cf6156Isup2.hkl
Contains datablock I

CCDC reference: 183773

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.029
  • wR factor = 0.072
  • Data-to-parameter ratio = 13.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.02 From the CIF: _reflns_number_total 1304 Count of symmetry unique reflns 663 Completeness (_total/calc) 196.68% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 641 Fraction of Friedel pairs measured 0.967 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); 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) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: PLATON (Spek, 1990) and SHELXL.

'2H-thiochromene-2-one' top
Crystal data top
C9H6OSF(000) = 168
Mr = 162.20Dx = 1.442 Mg m3
Monoclinic, PcMelting point: 354 K
Hall symbol: P -2ycMo Kα radiation, λ = 0.71073 Å
a = 3.8899 (5) ÅCell parameters from 2232 reflections
b = 8.4355 (11) Åθ = 2.4–24.9°
c = 11.4569 (15) ŵ = 0.36 mm1
β = 96.530 (5)°T = 293 K
V = 373.50 (8) Å3Block, pale pink
Z = 20.40 × 0.21 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1253 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 25.0°, θmin = 2.4°
φ and ω scansh = 44
3453 measured reflectionsk = 109
1304 independent reflectionsl = 1313
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)] = 0.029H-atom parameters constrained
wR(F2) = 0.072 w = 1/[σ2(Fo2) + (0.0459P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1304 reflectionsΔρmax = 0.18 e Å3
100 parametersΔρmin = 0.15 e Å3
2 restraintsAbsolute structure: Flack (1983); 644 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (8)
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.

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
S10.75064 (9)0.17066 (6)0.08296 (5)0.04768 (18)
C80.5386 (5)0.3008 (2)0.0186 (2)0.0403 (5)
C90.4161 (5)0.2541 (3)0.13238 (18)0.0408 (5)
C70.4920 (6)0.4545 (3)0.0184 (2)0.0512 (5)
H70.57630.48460.09440.061*
C30.4673 (5)0.0962 (3)0.17322 (18)0.0481 (5)
H30.38110.07350.25050.058*
C40.2449 (6)0.3674 (3)0.2068 (2)0.0538 (6)
H40.16130.33890.28320.065*
C20.6255 (6)0.0200 (3)0.1113 (2)0.0518 (5)
H20.64140.11680.14920.062*
C10.7745 (6)0.0109 (3)0.0083 (2)0.0493 (5)
C60.3235 (7)0.5620 (3)0.0559 (2)0.0605 (6)
H60.29200.66520.03050.073*
O10.9222 (5)0.1185 (2)0.06346 (17)0.0756 (6)
C50.1979 (6)0.5177 (3)0.1701 (3)0.0600 (6)
H50.08240.59110.22090.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0555 (3)0.0497 (3)0.0360 (2)0.0027 (3)0.00344 (18)0.0000 (3)
C80.0376 (11)0.0433 (11)0.0407 (11)0.0019 (8)0.0080 (8)0.0025 (8)
C90.0399 (10)0.0448 (12)0.0378 (10)0.0049 (9)0.0050 (8)0.0031 (9)
C70.0569 (13)0.0448 (13)0.0527 (13)0.0013 (10)0.0099 (11)0.0073 (10)
C30.0571 (13)0.0486 (13)0.0376 (10)0.0049 (10)0.0015 (9)0.0031 (10)
C40.0540 (13)0.0595 (15)0.0465 (13)0.0011 (11)0.0000 (10)0.0122 (11)
C20.0673 (14)0.0404 (12)0.0476 (13)0.0004 (10)0.0067 (11)0.0075 (10)
C10.0564 (13)0.0436 (12)0.0474 (13)0.0067 (9)0.0034 (10)0.0026 (9)
C60.0622 (13)0.0428 (13)0.0786 (18)0.0050 (11)0.0178 (12)0.0013 (12)
O10.0995 (14)0.0565 (10)0.0669 (12)0.0267 (10)0.0079 (10)0.0083 (9)
C50.0594 (18)0.0519 (15)0.0675 (15)0.0089 (12)0.0022 (12)0.0185 (12)
Geometric parameters (Å, º) top
S1—C81.738 (2)C3—H30.930
S1—C11.762 (2)C4—C51.355 (4)
C8—C71.383 (3)C4—H40.930
C8—C91.393 (3)C2—C11.428 (3)
C9—C41.398 (3)C2—H20.930
C9—C31.433 (3)C1—O11.213 (3)
C7—C61.360 (3)C6—C51.395 (4)
C7—H70.930C6—H60.930
C3—C21.320 (3)C5—H50.930
C8—S1—C1105.74 (10)C5—C4—H4119.3
C7—C8—C9120.6 (2)C9—C4—H4119.3
C7—C8—S1117.14 (17)C3—C2—C1126.1 (2)
C9—C8—S1122.27 (16)C3—C2—H2116.9
C8—C9—C4117.8 (2)C1—C2—H2116.9
C8—C9—C3121.50 (19)O1—C1—C2125.2 (2)
C4—C9—C3120.7 (2)O1—C1—S1116.45 (18)
C6—C7—C8120.3 (2)C2—C1—S1118.31 (17)
C6—C7—H7119.9C7—C6—C5120.1 (2)
C8—C7—H7119.9C7—C6—H6120.0
C2—C3—C9126.04 (19)C5—C6—H6120.0
C2—C3—H3117.0C4—C5—C6119.8 (2)
C9—C3—H3117.0C4—C5—H5120.1
C5—C4—C9121.5 (2)C6—C5—H5120.1
 

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