Buy article online - an online subscription or single-article purchase is required to access this article.
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
CCDC reference: 183773
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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.
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.
'2
H-thiochromene-2-one'
top
Crystal data top
C9H6OS | F(000) = 168 |
Mr = 162.20 | Dx = 1.442 Mg m−3 |
Monoclinic, Pc | Melting point: 354 K |
Hall symbol: P -2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 3.8899 (5) Å | Cell parameters from 2232 reflections |
b = 8.4355 (11) Å | θ = 2.4–24.9° |
c = 11.4569 (15) Å | µ = 0.36 mm−1 |
β = 96.530 (5)° | T = 293 K |
V = 373.50 (8) Å3 | Block, pale pink |
Z = 2 | 0.40 × 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 tube | Rint = 0.037 |
Graphite monochromator | θmax = 25.0°, θmin = 2.4° |
φ and ω scans | h = −4→4 |
3453 measured reflections | k = −10→9 |
1304 independent reflections | l = −13→13 |
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)] = 0.029 | H-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 reflections | Δρmax = 0.18 e Å−3 |
100 parameters | Δρmin = −0.15 e Å−3 |
2 restraints | Absolute structure: Flack (1983); 644 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
S1 | 0.75064 (9) | 0.17066 (6) | 0.08296 (5) | 0.04768 (18) | |
C8 | 0.5386 (5) | 0.3008 (2) | −0.0186 (2) | 0.0403 (5) | |
C9 | 0.4161 (5) | 0.2541 (3) | −0.13238 (18) | 0.0408 (5) | |
C7 | 0.4920 (6) | 0.4545 (3) | 0.0184 (2) | 0.0512 (5) | |
H7 | 0.5763 | 0.4846 | 0.0944 | 0.061* | |
C3 | 0.4673 (5) | 0.0962 (3) | −0.17322 (18) | 0.0481 (5) | |
H3 | 0.3811 | 0.0735 | −0.2505 | 0.058* | |
C4 | 0.2449 (6) | 0.3674 (3) | −0.2068 (2) | 0.0538 (6) | |
H4 | 0.1613 | 0.3389 | −0.2832 | 0.065* | |
C2 | 0.6255 (6) | −0.0200 (3) | −0.1113 (2) | 0.0518 (5) | |
H2 | 0.6414 | −0.1168 | −0.1492 | 0.062* | |
C1 | 0.7745 (6) | −0.0109 (3) | 0.0083 (2) | 0.0493 (5) | |
C6 | 0.3235 (7) | 0.5620 (3) | −0.0559 (2) | 0.0605 (6) | |
H6 | 0.2920 | 0.6652 | −0.0305 | 0.073* | |
O1 | 0.9222 (5) | −0.1185 (2) | 0.06346 (17) | 0.0756 (6) | |
C5 | 0.1979 (6) | 0.5177 (3) | −0.1701 (3) | 0.0600 (6) | |
H5 | 0.0824 | 0.5911 | −0.2209 | 0.072* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0555 (3) | 0.0497 (3) | 0.0360 (2) | 0.0027 (3) | −0.00344 (18) | 0.0000 (3) |
C8 | 0.0376 (11) | 0.0433 (11) | 0.0407 (11) | −0.0019 (8) | 0.0080 (8) | 0.0025 (8) |
C9 | 0.0399 (10) | 0.0448 (12) | 0.0378 (10) | −0.0049 (9) | 0.0050 (8) | 0.0031 (9) |
C7 | 0.0569 (13) | 0.0448 (13) | 0.0527 (13) | −0.0013 (10) | 0.0099 (11) | −0.0073 (10) |
C3 | 0.0571 (13) | 0.0486 (13) | 0.0376 (10) | −0.0049 (10) | 0.0015 (9) | −0.0031 (10) |
C4 | 0.0540 (13) | 0.0595 (15) | 0.0465 (13) | −0.0011 (11) | 0.0000 (10) | 0.0122 (11) |
C2 | 0.0673 (14) | 0.0404 (12) | 0.0476 (13) | −0.0004 (10) | 0.0067 (11) | −0.0075 (10) |
C1 | 0.0564 (13) | 0.0436 (12) | 0.0474 (13) | 0.0067 (9) | 0.0034 (10) | 0.0026 (9) |
C6 | 0.0622 (13) | 0.0428 (13) | 0.0786 (18) | 0.0050 (11) | 0.0178 (12) | 0.0013 (12) |
O1 | 0.0995 (14) | 0.0565 (10) | 0.0669 (12) | 0.0267 (10) | −0.0079 (10) | 0.0083 (9) |
C5 | 0.0594 (18) | 0.0519 (15) | 0.0675 (15) | 0.0089 (12) | 0.0022 (12) | 0.0185 (12) |
Geometric parameters (Å, º) top
S1—C8 | 1.738 (2) | C3—H3 | 0.930 |
S1—C1 | 1.762 (2) | C4—C5 | 1.355 (4) |
C8—C7 | 1.383 (3) | C4—H4 | 0.930 |
C8—C9 | 1.393 (3) | C2—C1 | 1.428 (3) |
C9—C4 | 1.398 (3) | C2—H2 | 0.930 |
C9—C3 | 1.433 (3) | C1—O1 | 1.213 (3) |
C7—C6 | 1.360 (3) | C6—C5 | 1.395 (4) |
C7—H7 | 0.930 | C6—H6 | 0.930 |
C3—C2 | 1.320 (3) | C5—H5 | 0.930 |
| | | |
C8—S1—C1 | 105.74 (10) | C5—C4—H4 | 119.3 |
C7—C8—C9 | 120.6 (2) | C9—C4—H4 | 119.3 |
C7—C8—S1 | 117.14 (17) | C3—C2—C1 | 126.1 (2) |
C9—C8—S1 | 122.27 (16) | C3—C2—H2 | 116.9 |
C8—C9—C4 | 117.8 (2) | C1—C2—H2 | 116.9 |
C8—C9—C3 | 121.50 (19) | O1—C1—C2 | 125.2 (2) |
C4—C9—C3 | 120.7 (2) | O1—C1—S1 | 116.45 (18) |
C6—C7—C8 | 120.3 (2) | C2—C1—S1 | 118.31 (17) |
C6—C7—H7 | 119.9 | C7—C6—C5 | 120.1 (2) |
C8—C7—H7 | 119.9 | C7—C6—H6 | 120.0 |
C2—C3—C9 | 126.04 (19) | C5—C6—H6 | 120.0 |
C2—C3—H3 | 117.0 | C4—C5—C6 | 119.8 (2) |
C9—C3—H3 | 117.0 | C4—C5—H5 | 120.1 |
C5—C4—C9 | 121.5 (2) | C6—C5—H5 | 120.1 |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.