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The title compound, C12H9AsOS3, has a mirror plane so that one thienyl group as well as the As and O atoms lie on that plane. The As atom exists in a distorted tetrahedral geometry with a range of angles of 107.73 (8) to 112.82 (13)°, with an As=O bond distance of 1.648 (2) Å and As-C distances of 1.893 (3)-1.895 (2) Å.
Supporting information
CCDC reference: 177227
Key indicators
- Single-crystal X-ray study
- T = 223 K
- Mean (C-C) = 0.004 Å
- R factor = 0.035
- wR factor = 0.089
- Data-to-parameter ratio = 22.0
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: SMART (Bruker, 2000a); cell refinement: SAINT (Bruker, 2000a); data reduction: SHELXTL (Bruker, 2000a); program(s) used to solve structure: DIRDIF92 PATTY (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHEXLTL.
Crystal data top
C12H9AsOS3 | Dx = 1.751 Mg m−3 |
Mr = 340.29 | Mo Kα radiation, λ = 0.71069 Å |
Orthorhombic, Pnma | Cell parameters from 10145 reflections |
a = 15.2840 (4) Å | θ = 2.7–30.0° |
b = 13.9364 (4) Å | µ = 3.10 mm−1 |
c = 6.0585 (2) Å | T = 223 K |
V = 1290.48 (7) Å3 | Block, colourless |
Z = 4 | 0.23 × 0.19 × 0.16 mm |
F(000) = 680 | |
Data collection top
Bruker AXS SMART CCD diffractometer | 1958 independent reflections |
Radiation source: fine-focus sealed tube | 1893 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω scans | θmax = 30.0°, θmin = 2.7° |
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2000b) | h = −21→21 |
Tmin = 0.481, Tmax = 0.609 | k = −17→19 |
10145 measured reflections | l = −6→8 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0497P)2 + 1.0951P] where P = (Fo2 + 2Fc2)/3 |
1958 reflections | (Δ/σ)max < 0.001 |
89 parameters | Δρmax = 0.67 e Å−3 |
0 restraints | Δρmin = −0.65 e Å−3 |
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 | |
As | 0.491489 (19) | 0.2500 | 0.40629 (5) | 0.02066 (11) | |
S1 | 0.69149 (5) | 0.2500 | 0.33209 (13) | 0.02570 (17) | |
S2 | 0.36740 (4) | 0.07707 (4) | 0.33997 (11) | 0.03452 (16) | |
O1 | 0.48821 (16) | 0.2500 | 0.1344 (4) | 0.0300 (5) | |
C1 | 0.60704 (18) | 0.2500 | 0.5187 (5) | 0.0220 (5) | |
C2 | 0.7679 (2) | 0.2500 | 0.5381 (6) | 0.0277 (6) | |
H2 | 0.8287 | 0.2500 | 0.5142 | 0.053 (5)* | |
C3 | 0.7300 (2) | 0.2500 | 0.7399 (6) | 0.0348 (8) | |
H3 | 0.7618 | 0.2500 | 0.8727 | 0.053 (5)* | |
C4 | 0.6364 (2) | 0.2500 | 0.7304 (6) | 0.0309 (7) | |
H4 | 0.5999 | 0.2500 | 0.8551 | 0.053 (5)* | |
C5 | 0.43421 (13) | 0.13932 (15) | 0.5163 (4) | 0.0234 (4) | |
C6 | 0.34031 (17) | −0.00300 (17) | 0.5392 (5) | 0.0356 (5) | |
H6 | 0.3016 | −0.0546 | 0.5174 | 0.053 (5)* | |
C7 | 0.38061 (19) | 0.01568 (19) | 0.7329 (5) | 0.0375 (5) | |
H7 | 0.3734 | −0.0220 | 0.8603 | 0.053 (5)* | |
C8 | 0.43509 (17) | 0.09822 (19) | 0.7242 (4) | 0.0327 (5) | |
H8 | 0.4676 | 0.1219 | 0.8442 | 0.053 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
As | 0.01585 (15) | 0.02512 (17) | 0.02101 (17) | 0.000 | −0.00022 (10) | 0.000 |
S1 | 0.0200 (3) | 0.0335 (4) | 0.0236 (4) | 0.000 | 0.0035 (3) | 0.000 |
S2 | 0.0350 (3) | 0.0318 (3) | 0.0368 (3) | −0.0067 (2) | −0.0106 (2) | 0.0005 (2) |
O1 | 0.0295 (12) | 0.0409 (14) | 0.0197 (10) | 0.000 | −0.0016 (8) | 0.000 |
C1 | 0.0135 (11) | 0.0280 (13) | 0.0246 (13) | 0.000 | 0.0020 (10) | 0.000 |
C2 | 0.0158 (12) | 0.0347 (16) | 0.0324 (15) | 0.000 | 0.0001 (11) | 0.000 |
C3 | 0.0208 (14) | 0.056 (2) | 0.0275 (16) | 0.000 | −0.0044 (12) | 0.000 |
C4 | 0.0192 (13) | 0.0470 (19) | 0.0266 (15) | 0.000 | 0.0017 (11) | 0.000 |
C5 | 0.0190 (9) | 0.0246 (9) | 0.0267 (10) | −0.0011 (7) | −0.0008 (7) | −0.0022 (8) |
C6 | 0.0308 (12) | 0.0262 (11) | 0.0498 (14) | −0.0050 (9) | 0.0004 (11) | 0.0034 (10) |
C7 | 0.0425 (14) | 0.0320 (12) | 0.0380 (13) | −0.0037 (10) | 0.0054 (11) | 0.0068 (10) |
C8 | 0.0342 (12) | 0.0351 (12) | 0.0289 (11) | −0.0076 (10) | 0.0009 (9) | 0.0002 (9) |
Geometric parameters (Å, º) top
As—O1 | 1.648 (2) | C3—C4 | 1.431 (5) |
As—C1 | 1.893 (3) | C5—C8 | 1.384 (3) |
As—C5 | 1.895 (2) | C6—C7 | 1.351 (4) |
As—C5i | 1.895 (2) | C7—C8 | 1.421 (4) |
S1—C2 | 1.710 (3) | C2—H2 | 0.9400 |
S1—C1 | 1.716 (3) | C3—H3 | 0.9400 |
S2—C6 | 1.695 (3) | C4—H4 | 0.9400 |
S2—C5 | 1.714 (2) | C6—H6 | 0.9400 |
C1—C4 | 1.359 (4) | C7—H7 | 0.9400 |
C2—C3 | 1.353 (5) | C8—H8 | 0.9400 |
| | | |
O1—As—C1 | 112.82 (13) | S2—C5—As | 117.92 (12) |
O1—As—C5 | 109.73 (8) | C7—C6—S2 | 112.36 (19) |
C1—As—C5 | 107.73 (8) | C6—C7—C8 | 113.0 (2) |
O1—As—C5i | 109.73 (8) | C5—C8—C7 | 111.3 (2) |
C1—As—C5i | 107.73 (8) | C3—C2—H2 | 124.2 |
C5—As—C5i | 109.00 (13) | S1—C2—H2 | 124.2 |
C2—S1—C1 | 91.89 (16) | C2—C3—H3 | 123.5 |
C6—S2—C5 | 92.00 (12) | C4—C3—H3 | 123.5 |
C4—C1—S1 | 111.9 (2) | C1—C4—H4 | 124.2 |
C4—C1—As | 130.4 (2) | C3—C4—H4 | 124.2 |
S1—C1—As | 117.71 (17) | C7—C6—H6 | 123.8 |
C3—C2—S1 | 111.5 (2) | S2—C6—H6 | 123.8 |
C2—C3—C4 | 113.1 (3) | C6—C7—H7 | 123.5 |
C1—C4—C3 | 111.6 (3) | C8—C7—H7 | 123.5 |
C8—C5—S2 | 111.32 (16) | C5—C8—H8 | 124.3 |
C8—C5—As | 130.75 (17) | C7—C8—H8 | 124.3 |
Symmetry code: (i) x, −y+1/2, z. |
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