


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810037281/jh2201sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810037281/jh2201Isup2.hkl |
CCDC reference: 759469
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean
(C-C) = 0.006 Å
- R factor = 0.068
- wR factor = 0.153
- Data-to-parameter ratio = 17.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 6 PLAT480_ALERT_4_C Long H...A H-Bond Reported H7C .. S1 .. 2.93 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C13 H24 S4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The synthesis of I has been described elsewhere (Gâz et al., 2008). Crystal were obtained from dichloromethane, by slow evaporation at room temperature.
All hydrogen atoms were placed in calculated positions using a riding model, with C—H = 0.93–0.97 Å and with Uiso = 1.5Ueq (C) for H. The methyl groups were allowed to rotate but not to tip.
Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg & Putz, 2004); software used to prepare material for publication: publCIF (Westrip, 2010).
C13H24S4 | F(000) = 664 |
Mr = 308.56 | Dx = 1.268 Mg m−3 |
Monoclinic, C2/c | Melting point = 416–418 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 16.701 (5) Å | Cell parameters from 3441 reflections |
b = 10.241 (3) Å | θ = 2.5–28.1° |
c = 12.063 (3) Å | µ = 0.57 mm−1 |
β = 128.418 (4)° | T = 297 K |
V = 1616.5 (8) Å3 | Block, colourless |
Z = 4 | 0.32 × 0.31 × 0.28 mm |
Bruker SMART APEX CCD area-detector diffractometer | 1432 independent reflections |
Radiation source: fine-focus sealed tube | 1311 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −19→19 |
Tmin = 0.839, Tmax = 0.857 | k = −12→12 |
7606 measured reflections | l = −14→14 |
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.153 | H-atom parameters constrained |
S = 1.27 | w = 1/[σ2(Fo2) + (0.0592P)2 + 2.605P] where P = (Fo2 + 2Fc2)/3 |
1432 reflections | (Δ/σ)max < 0.001 |
80 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C13H24S4 | V = 1616.5 (8) Å3 |
Mr = 308.56 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 16.701 (5) Å | µ = 0.57 mm−1 |
b = 10.241 (3) Å | T = 297 K |
c = 12.063 (3) Å | 0.32 × 0.31 × 0.28 mm |
β = 128.418 (4)° |
Bruker SMART APEX CCD area-detector diffractometer | 1432 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1311 reflections with I > 2σ(I) |
Tmin = 0.839, Tmax = 0.857 | Rint = 0.035 |
7606 measured reflections |
R[F2 > 2σ(F2)] = 0.068 | 0 restraints |
wR(F2) = 0.153 | H-atom parameters constrained |
S = 1.27 | Δρmax = 0.36 e Å−3 |
1432 reflections | Δρmin = −0.28 e Å−3 |
80 parameters |
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 | ||
C1 | 0.5000 | 0.7036 (5) | 1.2500 | 0.0439 (11) | |
C2 | 0.4969 (3) | 0.6137 (4) | 1.1462 (4) | 0.0596 (11) | |
H2A | 0.4357 | 0.5606 | 1.0981 | 0.071* | |
H2B | 0.5551 | 0.5551 | 1.2001 | 0.071* | |
C3 | 0.3816 (3) | 0.7866 (4) | 0.9229 (4) | 0.0486 (9) | |
H3 | 0.3245 | 0.7260 | 0.8842 | 0.058* | |
C4 | 0.4026 (3) | 0.7860 (4) | 1.1697 (4) | 0.0484 (9) | |
H4A | 0.4024 | 0.8353 | 1.2382 | 0.058* | |
H4B | 0.3444 | 0.7273 | 1.1218 | 0.058* | |
C5 | 0.3655 (3) | 0.8601 (4) | 0.7999 (4) | 0.0585 (11) | |
H5 | 0.4243 | 0.9179 | 0.8388 | 0.070* | |
C6 | 0.3597 (5) | 0.7656 (6) | 0.6974 (5) | 0.103 (2) | |
H6A | 0.2997 | 0.7123 | 0.6529 | 0.154* | |
H6B | 0.4193 | 0.7110 | 0.7483 | 0.154* | |
H6C | 0.3564 | 0.8140 | 0.6266 | 0.154* | |
C7 | 0.2696 (4) | 0.9437 (6) | 0.7207 (5) | 0.0846 (16) | |
H7A | 0.2571 | 0.9797 | 0.6377 | 0.127* | |
H7B | 0.2786 | 1.0132 | 0.7809 | 0.127* | |
H7C | 0.2124 | 0.8908 | 0.6934 | 0.127* | |
S1 | 0.49848 (9) | 0.69295 (11) | 1.01407 (11) | 0.0627 (4) | |
S2 | 0.38431 (7) | 0.89852 (9) | 1.04130 (10) | 0.0529 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.050 (3) | 0.036 (3) | 0.041 (3) | 0.000 | 0.026 (2) | 0.000 |
C2 | 0.076 (3) | 0.050 (2) | 0.049 (2) | 0.016 (2) | 0.037 (2) | 0.0054 (18) |
C3 | 0.047 (2) | 0.048 (2) | 0.044 (2) | −0.0022 (16) | 0.0251 (18) | 0.0052 (16) |
C4 | 0.040 (2) | 0.055 (2) | 0.046 (2) | −0.0010 (16) | 0.0251 (17) | −0.0052 (17) |
C5 | 0.055 (2) | 0.061 (2) | 0.050 (2) | −0.0053 (19) | 0.028 (2) | 0.0109 (19) |
C6 | 0.139 (5) | 0.112 (5) | 0.061 (3) | 0.014 (4) | 0.064 (4) | 0.018 (3) |
C7 | 0.062 (3) | 0.102 (4) | 0.068 (3) | 0.014 (3) | 0.029 (2) | 0.039 (3) |
S1 | 0.0744 (8) | 0.0695 (7) | 0.0527 (6) | 0.0285 (6) | 0.0437 (6) | 0.0142 (5) |
S2 | 0.0497 (6) | 0.0444 (6) | 0.0520 (6) | 0.0097 (4) | 0.0254 (5) | 0.0033 (4) |
C1—C4i | 1.529 (4) | C4—H4A | 0.9700 |
C1—C4 | 1.529 (4) | C4—H4B | 0.9700 |
C1—C2 | 1.529 (5) | C5—C7 | 1.520 (6) |
C1—C2i | 1.529 (5) | C5—C6 | 1.524 (7) |
C2—S1 | 1.803 (4) | C5—H5 | 0.9800 |
C2—H2A | 0.9700 | C6—H6A | 0.9600 |
C2—H2B | 0.9700 | C6—H6B | 0.9600 |
C3—C5 | 1.531 (5) | C6—H6C | 0.9600 |
C3—S1 | 1.809 (4) | C7—H7A | 0.9600 |
C3—S2 | 1.810 (4) | C7—H7B | 0.9600 |
C3—H3 | 0.9800 | C7—H7C | 0.9600 |
C4—S2 | 1.798 (4) | ||
C4i—C1—C4 | 113.0 (4) | S2—C4—H4B | 108.2 |
C4i—C1—C2 | 109.4 (2) | H4A—C4—H4B | 107.4 |
C4—C1—C2 | 109.4 (2) | C7—C5—C6 | 109.7 (4) |
C4i—C1—C2i | 109.4 (2) | C7—C5—C3 | 111.6 (4) |
C4—C1—C2i | 109.4 (2) | C6—C5—C3 | 111.0 (4) |
C2—C1—C2i | 106.0 (4) | C7—C5—H5 | 108.2 |
C1—C2—S1 | 116.2 (3) | C6—C5—H5 | 108.2 |
C1—C2—H2A | 108.2 | C3—C5—H5 | 108.2 |
S1—C2—H2A | 108.2 | C5—C6—H6A | 109.5 |
C1—C2—H2B | 108.2 | C5—C6—H6B | 109.5 |
S1—C2—H2B | 108.2 | H6A—C6—H6B | 109.5 |
H2A—C2—H2B | 107.4 | C5—C6—H6C | 109.5 |
C5—C3—S1 | 108.9 (3) | H6A—C6—H6C | 109.5 |
C5—C3—S2 | 110.9 (3) | H6B—C6—H6C | 109.5 |
S1—C3—S2 | 111.59 (19) | C5—C7—H7A | 109.5 |
C5—C3—H3 | 108.5 | C5—C7—H7B | 109.5 |
S1—C3—H3 | 108.5 | H7A—C7—H7B | 109.5 |
S2—C3—H3 | 108.5 | C5—C7—H7C | 109.5 |
C1—C4—S2 | 116.3 (2) | H7A—C7—H7C | 109.5 |
C1—C4—H4A | 108.2 | H7B—C7—H7C | 109.5 |
S2—C4—H4A | 108.2 | C2—S1—C3 | 99.99 (18) |
C1—C4—H4B | 108.2 | C4—S2—C3 | 100.49 (17) |
C4i—C1—C2—S1 | −59.6 (4) | S1—C3—C5—C6 | 58.7 (4) |
C4—C1—C2—S1 | 64.8 (4) | S2—C3—C5—C6 | −178.1 (3) |
C2i—C1—C2—S1 | −177.4 (4) | C1—C2—S1—C3 | −61.4 (3) |
C4i—C1—C4—S2 | 58.00 (19) | C5—C3—S1—C2 | −178.1 (3) |
C2—C1—C4—S2 | −64.2 (4) | S2—C3—S1—C2 | 59.1 (2) |
C2i—C1—C4—S2 | −179.8 (2) | C1—C4—S2—C3 | 60.4 (3) |
S1—C3—C5—C7 | −178.6 (3) | C5—C3—S2—C4 | 179.5 (3) |
S2—C3—C5—C7 | −55.5 (4) | S1—C3—S2—C4 | −58.9 (2) |
Symmetry code: (i) −x+1, y, −z+5/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7C···S1ii | 0.96 | 2.93 | 3.827 (6) | 156 (1) |
Symmetry code: (ii) x−1/2, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C13H24S4 |
Mr | 308.56 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 297 |
a, b, c (Å) | 16.701 (5), 10.241 (3), 12.063 (3) |
β (°) | 128.418 (4) |
V (Å3) | 1616.5 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.57 |
Crystal size (mm) | 0.32 × 0.31 × 0.28 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.839, 0.857 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7606, 1432, 1311 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.153, 1.27 |
No. of reflections | 1432 |
No. of parameters | 80 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.36, −0.28 |
Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg & Putz, 2004), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7C···S1i | 0.961 | 2.928 | 3.827 (6) | 156.20 (4) |
Symmetry code: (i) x−1/2, −y+3/2, z−1/2. |
Despite the rich literature dealing with spiro compounds (Cismaş et al., 2005; Eliel & Wilen, 1994; Grosu et al., 1995, 1997; Terec et al., 2001, 2004) new papers were written recently especially including spiro derivatives having sulfur or selenium heteroatoms. Only few spirans bearing 1,3 dithiane units were reported (Backer & Evenhuis, 1937; Gâz et al., 2008; Mitkin et al., 2001) and only 2 crystals were obtained so far (Zhou et al., 2001). The title compound (Fig. 1) exhibits a C2 symmetry unit with chair conformation for both six-membered rings.
Due to the space arrangement there are differences between positions 2, 4 and 2', 4'. Due to these differencies positions 4 and 4' which are oriented towards the other 1,3-dithiane ring are named methylene inside, while the other two CH2 groups (positions 2 and 2') are oriented in opposite direction and they are named methylene outside groups.
In the crystal packing (Fig. 2 and Fig. 3) the sulfur atom from a neighbour molecule is hydrogen-bonded (weak interactions) via a intermolecular C7—H7c ···S1 connection (Table 1).
These weak interactions stabilize the lattice and form a three-dimensional network as a channel-like arrangement along the c axis.