(1RS,4RS)-1-Methoxy­spiro­[bicyclo­[2.2.2]oct-5-ene-2,2′-[1′,3′]dithiol­ane]. Corrigendum

Gültekin, Z.; Adams, H.; Hökelek, T.

doi:10.1107/S1600536806003072

addenda and errata

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 62| Part 2| February 2006| Pages e6-e7

https://doi.org/10.1107/S1600536806003072

(1RS,4RS)-1-Methoxyspiro[bicyclo[2.2.2]oct-5-ene-2,2′-[1′,3′]dithiolane]. Corrigendum

Zeynep Gültekin,^a Harry Adams ^b and Tuncer Hökelek ^c ^*

^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

(Received 20 January 2006; accepted 25 January 2006; online 31 January 2006)

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.

Figure 1
A view of the molecular structure, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

2. Experimental

2.1.3. Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.144
S = 1.02
1983 reflections
133 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F_o²) + (0.0805P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

S1—C7	1.802 (5)
S1—C2	1.823 (4)
S2—C8	1.774 (7)
S2—C2	1.844 (4)
O1—C1	1.416 (4)
O1—C9	1.420 (5)
C1—C10	1.506 (6)
C1—C3	1.516 (6)
C2—C1	1.558 (5)
C2—C6	1.566 (5)
C4—C3	1.511 (7)
C4—C5	1.529 (7)
C5—C6	1.536 (8)
C7—C8	1.467 (9)
C11—C10	1.332 (7)
C11—C5	1.502 (7)

C7—S1—C2	97.3 (2)
C8—S2—C2	99.3 (2)
C1—O1—C9	116.2 (3)
O1—C1—C10	114.9 (3)
O1—C1—C3	112.7 (3)
O1—C1—C2	106.6 (3)
C3—C1—C2	107.1 (3)
C1—C2—S1	113.8 (2)
C6—C2—S1	108.4 (3)
C1—C2—S2	110.7 (3)
C6—C2—S2	110.4 (3)
S1—C2—S2	106.1 (2)
C4—C3—C1	112.1 (3)
C4—C5—C6	106.0 (4)
C8—C7—S1	109.5 (4)
C7—C8—S2	114.0 (4)
C11—C10—C1	114.7 (4)
C10—C11—C5	114.0 (4)

C7—S1—C2—S2	30.0 (3)
C2—S1—C7—C8	−37.9 (5)
C2—S2—C8—C7	−9.2 (5)
C8—S2—C2—S1	−15.6 (3)
C9—O1—C1—C3	−70.9 (5)
S1—C2—C1—O1	56.8 (4)
S2—C2—C1—O1	−62.5 (3)
S1—C7—C8—S2	31.2 (6)

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 U_iso(H) = xU_eq(carrier atom), where x = 1.5 for methyl H atoms and x = 1.2 for all others.

Data collection: XSCANS (Siemens, 1996 ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536806003072/wn9163sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806003072/wn9163Isup2.hkl

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: 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).

(1RS,4RS)-1-Methoxyspiro[bicyclo[2.2.2]oct-5-ene-2,2'-[1',3']dithiolane] top

Crystal data top

C₁₁H₁₆OS₂	Z = 2
M_r = 228.36	F(000) = 244
Triclinic, P1	D_x = 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

Data collection top

Siemens P4 diffractometer	R_int = 0.037
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 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 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)] = 0.058	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(F_o²) + (0.0805P)²] where P = (F_o² + 2F_c²)/3
1983 reflections	(Δ/σ)_max < 0.001
133 parameters	Δρ_max = 0.30 e Å⁻³
6 restraints	Δρ_min = −0.22 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	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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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Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
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