addenda and errata
(1RS,4RS)-1-Methoxyspiro[bicyclo[2.2.2]oct-5-ene-2,2′-[1′,3′]dithiolane]. Corrigendum
aZonguldak Karaelmas University, Department of Chemistry, 067100 Zonguldak, Turkey, bUniversity of Sheffield, Department of Chemistry, Sheffield S3 7HF, England, and cHacettepe University, Department of Physics, 06532 Beytepe Ankara, Turkey
*Correspondence e-mail: merzifon@hacettepe.edu.tr
In the paper by Gültekin, Adams & Hökelek [Acta Cryst. (2003), E59, o926–o928], the placement of H atoms bonded to C3, C4, C10 and C11 is wrong. C10=C11 is a double bond, but there are two H atoms on each C atom instead of one. On the other hand, C3—C4 is a single bond and there is one H atom on each C atom instead of two. The structure has now been rerefined with the correct assignment of H atoms and the structure is shown in Fig. 1.
2. Experimental
2.1.3. Refinement
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Atoms H10 and H11 were located in a difference map and refined isotropically [C—H = 0.96 (2)–0.99 (2) Å]. The other H atoms were positioned geometrically, with C—H = 0.96, 0.97 and 0.98 Å for methyl, methylene and methine H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(carrier atom), where x = 1.5 for methyl H atoms and x = 1.2 for all others.
Data collection: XSCANS (Siemens, 1996); cell XSCANS; data reduction: SHELXTL (Bruker, 1997); 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); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
https://doi.org/10.1107/S1600536806003072/wn9163sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806003072/wn9163Isup2.hkl
Data collection: XSCANS (Siemens, 1996); cell
XSCANS; data reduction: SHELXTL (Bruker, 1997); 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); software used to prepare material for publication: WinGX (Farrugia, 1999).C11H16OS2 | Z = 2 |
Mr = 228.36 | F(000) = 244 |
Triclinic, P1 | Dx = 1.342 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.748 (4) Å | Cell parameters from 25 reflections |
b = 7.870 (4) Å | θ = 12–20° |
c = 11.474 (7) Å | µ = 0.44 mm−1 |
α = 99.23 (4)° | T = 293 K |
β = 103.00 (5)° | Block, colorless |
γ = 102.69 (3)° | 0.55 × 0.34 × 0.28 mm |
V = 564.9 (6) Å3 |
Siemens P4 diffractometer | Rint = 0.037 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.7° |
Graphite monochromator | h = −1→8 |
non–profiled ω scans | k = −9→9 |
2493 measured reflections | l = −13→13 |
1983 independent reflections | 3 standard reflections every 100 reflections |
1040 reflections with I > 2σ(I) | intensity decay: 1% |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0805P)2] where P = (Fo2 + 2Fc2)/3 |
1983 reflections | (Δ/σ)max < 0.001 |
133 parameters | Δρmax = 0.30 e Å−3 |
6 restraints | Δρmin = −0.22 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.14528 (18) | 0.75241 (15) | 0.10473 (10) | 0.0530 (4) | |
S2 | −0.0295 (2) | 1.01482 (16) | 0.22939 (14) | 0.0668 (4) | |
O1 | 0.2275 (5) | 0.8109 (5) | 0.3843 (3) | 0.0615 (9) | |
C1 | 0.0184 (6) | 0.7119 (5) | 0.3203 (3) | 0.0403 (9) | |
C2 | −0.0367 (6) | 0.7759 (5) | 0.1983 (3) | 0.0389 (9) | |
C3 | −0.0041 (7) | 0.5130 (6) | 0.2860 (4) | 0.0540 (11) | |
C4 | −0.2285 (8) | 0.4089 (7) | 0.2191 (5) | 0.0670 (14) | |
C5 | −0.3620 (7) | 0.5409 (6) | 0.1991 (4) | 0.0589 (12) | |
C6 | −0.2629 (7) | 0.6603 (6) | 0.1225 (4) | 0.0571 (12) | |
C7 | 0.3242 (9) | 0.9721 (7) | 0.1652 (6) | 0.0780 (16) | |
C8 | 0.2042 (9) | 1.1024 (7) | 0.1882 (6) | 0.0796 (15) | |
C9 | 0.3010 (8) | 0.7912 (8) | 0.5062 (4) | 0.0679 (14) | |
C10 | −0.1471 (7) | 0.7445 (6) | 0.3834 (4) | 0.0524 (11) | |
C11 | −0.3444 (8) | 0.6569 (8) | 0.3204 (5) | 0.0657 (14) | |
H3A | 0.0876 | 0.4917 | 0.2343 | 0.065* | |
H3B | 0.0409 | 0.4707 | 0.3599 | 0.065* | |
H4A | −0.2839 | 0.3288 | 0.2671 | 0.080* | |
H4B | −0.2326 | 0.3380 | 0.1408 | 0.080* | |
H5 | −0.5095 | 0.4782 | 0.1566 | 0.071* | |
H6A | −0.3509 | 0.7379 | 0.0987 | 0.069* | |
H6B | −0.2542 | 0.5865 | 0.0484 | 0.069* | |
H7A | 0.4240 | 0.9733 | 0.2410 | 0.094* | |
H7B | 0.4027 | 1.0033 | 0.1071 | 0.094* | |
H8A | 0.1669 | 1.1482 | 0.1150 | 0.096* | |
H8B | 0.2940 | 1.2020 | 0.2535 | 0.096* | |
H9A | 0.4438 | 0.8629 | 0.5409 | 0.102* | |
H9B | 0.2957 | 0.6681 | 0.5055 | 0.102* | |
H9C | 0.2132 | 0.8293 | 0.5546 | 0.102* | |
H10 | −0.127 (8) | 0.869 (4) | 0.416 (5) | 0.097 (19)* | |
H11 | −0.438 (8) | 0.613 (10) | 0.371 (5) | 0.14 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0519 (7) | 0.0612 (7) | 0.0462 (6) | 0.0142 (5) | 0.0169 (5) | 0.0086 (5) |
S2 | 0.074 | 0.0470 (7) | 0.0913 (10) | 0.0230 (5) | 0.0366 (6) | 0.0178 (6) |
O1 | 0.0422 (18) | 0.084 (2) | 0.0387 (15) | −0.0088 (15) | −0.0036 (13) | 0.0145 (15) |
C1 | 0.0234 (18) | 0.053 (2) | 0.0344 (19) | 0.0040 (15) | −0.0018 (15) | 0.0045 (16) |
C2 | 0.032 (2) | 0.0438 (19) | 0.0374 (18) | 0.0113 (16) | 0.0040 (15) | 0.0055 (16) |
C3 | 0.044 (3) | 0.066 (3) | 0.055 (2) | 0.023 (2) | 0.009 (2) | 0.020 (2) |
C4 | 0.072 (3) | 0.054 (3) | 0.060 (3) | 0.002 (2) | 0.012 (2) | −0.002 (2) |
C5 | 0.035 (2) | 0.070 (3) | 0.053 (2) | −0.0014 (19) | −0.0009 (19) | 0.001 (2) |
C6 | 0.038 (2) | 0.056 (2) | 0.056 (3) | 0.0066 (19) | −0.016 (2) | 0.003 (2) |
C7 | 0.061 (3) | 0.068 (3) | 0.095 (4) | −0.004 (3) | 0.029 (3) | 0.008 (3) |
C8 | 0.071 | 0.058 (3) | 0.094 (4) | 0.009 (2) | 0.000 (3) | 0.014 (3) |
C9 | 0.058 (3) | 0.093 (4) | 0.035 (2) | 0.000 (3) | −0.004 (2) | 0.015 (2) |
C10 | 0.044 (2) | 0.053 (2) | 0.054 (2) | 0.0088 (19) | 0.012 (2) | 0.002 (2) |
C11 | 0.045 (3) | 0.089 (4) | 0.068 (3) | 0.021 (2) | 0.022 (2) | 0.018 (3) |
S1—C7 | 1.802 (5) | C5—C6 | 1.536 (8) |
S1—C2 | 1.823 (4) | C5—H5 | 0.9800 |
S2—C8 | 1.774 (7) | C6—H6A | 0.9700 |
S2—C2 | 1.844 (4) | C6—H6B | 0.9700 |
O1—C1 | 1.416 (4) | C7—C8 | 1.467 (9) |
O1—C9 | 1.420 (5) | C7—H7A | 0.9700 |
C1—C10 | 1.506 (6) | C7—H7B | 0.9700 |
C1—C3 | 1.516 (6) | C8—H8A | 0.9700 |
C2—C1 | 1.558 (5) | C8—H8B | 0.9700 |
C2—C6 | 1.566 (5) | C9—H9A | 0.9600 |
C3—H3A | 0.9700 | C9—H9B | 0.9600 |
C3—H3B | 0.9700 | C9—H9C | 0.9600 |
C4—C3 | 1.511 (7) | C10—H10 | 0.96 (2) |
C4—C5 | 1.529 (7) | C11—C10 | 1.332 (7) |
C4—H4A | 0.9700 | C11—C5 | 1.502 (7) |
C4—H4B | 0.9700 | C11—H11 | 0.99 (2) |
C7—S1—C2 | 97.3 (2) | C6—C5—H5 | 111.1 |
C8—S2—C2 | 99.3 (2) | C5—C6—C2 | 110.2 (4) |
C1—O1—C9 | 116.2 (3) | C5—C6—H6A | 109.6 |
O1—C1—C10 | 114.9 (3) | C2—C6—H6A | 109.6 |
O1—C1—C3 | 112.7 (3) | C5—C6—H6B | 109.6 |
C10—C1—C3 | 109.7 (3) | C2—C6—H6B | 109.6 |
O1—C1—C2 | 106.6 (3) | H6A—C6—H6B | 108.1 |
C10—C1—C2 | 105.2 (3) | C8—C7—S1 | 109.5 (4) |
C3—C1—C2 | 107.1 (3) | C8—C7—H7A | 109.8 |
C1—C2—C6 | 107.5 (3) | S1—C7—H7A | 109.8 |
C1—C2—S1 | 113.8 (2) | C8—C7—H7B | 109.8 |
C6—C2—S1 | 108.4 (3) | S1—C7—H7B | 109.8 |
C1—C2—S2 | 110.7 (3) | H7A—C7—H7B | 108.2 |
C6—C2—S2 | 110.4 (3) | C7—C8—S2 | 114.0 (4) |
S1—C2—S2 | 106.1 (2) | C7—C8—H8A | 108.8 |
C4—C3—C1 | 112.1 (3) | S2—C8—H8A | 108.8 |
C4—C3—H3A | 109.2 | C7—C8—H8B | 108.8 |
C1—C3—H3A | 109.2 | S2—C8—H8B | 108.8 |
C4—C3—H3B | 109.2 | H8A—C8—H8B | 107.7 |
C1—C3—H3B | 109.2 | O1—C9—H9A | 109.5 |
H3A—C3—H3B | 107.9 | O1—C9—H9B | 109.5 |
C3—C4—C5 | 108.6 (4) | H9A—C9—H9B | 109.5 |
C3—C4—H4A | 110.0 | O1—C9—H9C | 109.5 |
C5—C4—H4A | 110.0 | H9A—C9—H9C | 109.5 |
C3—C4—H4B | 110.0 | H9B—C9—H9C | 109.5 |
C5—C4—H4B | 110.0 | C11—C10—C1 | 114.7 (4) |
H4A—C4—H4B | 108.3 | C11—C10—H10 | 114 (3) |
C11—C5—C4 | 109.5 (4) | C1—C10—H10 | 112 (4) |
C11—C5—C6 | 108.0 (4) | C10—C11—C5 | 114.0 (4) |
C4—C5—C6 | 106.0 (4) | C10—C11—H11 | 115 (4) |
C11—C5—H5 | 111.1 | C5—C11—H11 | 119 (4) |
C4—C5—H5 | 111.1 | ||
C7—S1—C2—C1 | −91.9 (3) | S2—C2—C1—O1 | −62.5 (3) |
C7—S1—C2—C6 | 148.6 (3) | C6—C2—C1—C10 | −60.7 (4) |
C7—S1—C2—S2 | 30.0 (3) | S1—C2—C1—C10 | 179.3 (3) |
C2—S1—C7—C8 | −37.9 (5) | S2—C2—C1—C10 | 60.0 (3) |
C2—S2—C8—C7 | −9.2 (5) | C6—C2—C1—C3 | 56.0 (4) |
C8—S2—C2—C1 | 108.2 (3) | S1—C2—C1—C3 | −64.0 (4) |
C8—S2—C2—C6 | −132.9 (3) | S2—C2—C1—C3 | 176.7 (3) |
C8—S2—C2—S1 | −15.6 (3) | C1—C2—C6—C5 | 6.6 (4) |
C9—O1—C1—C10 | 55.7 (5) | S1—C2—C6—C5 | 129.9 (3) |
C9—O1—C1—C3 | −70.9 (5) | S2—C2—C6—C5 | −114.3 (4) |
C9—O1—C1—C2 | 171.9 (4) | C5—C4—C3—C1 | 3.8 (6) |
O1—C1—C3—C4 | 179.3 (4) | C3—C4—C5—C11 | −56.4 (5) |
C10—C1—C3—C4 | 50.0 (5) | C3—C4—C5—C6 | 59.8 (5) |
C2—C1—C3—C4 | −63.8 (5) | C11—C5—C6—C2 | 51.3 (5) |
O1—C1—C10—C11 | 177.3 (4) | C4—C5—C6—C2 | −65.9 (4) |
C3—C1—C10—C11 | −54.6 (5) | S1—C7—C8—S2 | 31.2 (6) |
C2—C1—C10—C11 | 60.3 (5) | C5—C11—C10—C1 | 0.7 (7) |
C6—C2—C1—O1 | 176.8 (3) | C10—C11—C5—C4 | 56.4 (6) |
S1—C2—C1—O1 | 56.8 (4) | C10—C11—C5—C6 | −58.6 (6) |
References
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