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The title compound, C13H18O2S5, possesses twofold symmetry and is composed of two pivalyl groups lying on opposite sides of the planar 1,3-dithiole-2-thione conjugated moiety. Owing to the introduction of the C=O electron-acceptor group the adjacent C-S bond length [1.774 (4) Å] is shorter than that of a typical C-S single bond. In the crystal structure, there are no significant intermolecular hydrogen bonds.
Supporting information
CCDC reference: 270552
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.061
- wR factor = 0.169
- Data-to-parameter ratio = 18.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
Alert level C
PLAT147_ALERT_1_C su on Symmetry Constrained Cell Angle(s) ....... ?
PLAT213_ALERT_2_C Atom S1 has ADP max/min Ratio ............. 3.20 prolat
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.88
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXTL (Bruker, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
4,5-Bis(pivaloylsulfanyl)-1,3-dithiolane-2-thione
top
Crystal data top
C13H18O2S5 | F(000) = 768 |
Mr = 366.57 | Dx = 1.372 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -C 2yc | Cell parameters from 57 reflections |
a = 23.469 (5) Å | θ = 4.4–12.5° |
b = 8.953 (5) Å | µ = 0.65 mm−1 |
c = 8.492 (5) Å | T = 293 K |
β = 95.879 (5)° | Prism, pale-yellow |
V = 1774.9 (15) Å3 | 0.40 × 0.36 × 0.32 mm |
Z = 4 | |
Data collection top
Bruker P4 diffractometer | 1332 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 26.0°, θmin = 2.4° |
ω scans | h = −1→28 |
Absorption correction: ψ scan (XSCANS; Bruker, 1997) | k = −1→11 |
Tmin = 0.762, Tmax = 0.843 | l = −10→10 |
2170 measured reflections | 3 standard reflections every 97 reflections |
1746 independent reflections | intensity decay: none |
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)] = 0.061 | H-atom parameters constrained |
wR(F2) = 0.170 | w = 1/[σ2(Fo2) + (0.0739P)2 + 4.6825P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
1746 reflections | Δρmax = 0.66 e Å−3 |
94 parameters | Δρmin = −0.47 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0128 (16) |
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 | |
C1 | 0.0000 | 0.1586 (6) | 0.2500 | 0.0696 (19) | |
C2 | 0.02496 (14) | 0.4396 (4) | 0.2176 (4) | 0.0427 (8) | |
C3 | 0.12931 (17) | 0.5834 (5) | 0.2417 (6) | 0.0595 (11) | |
C4 | 0.16726 (16) | 0.7188 (4) | 0.2268 (5) | 0.0504 (9) | |
C5 | 0.14658 (19) | 0.8195 (5) | 0.0896 (6) | 0.0690 (12) | |
H5A | 0.1473 | 0.7658 | −0.0080 | 0.103* | |
H5B | 0.1712 | 0.9052 | 0.0892 | 0.103* | |
H5C | 0.1081 | 0.8515 | 0.1005 | 0.103* | |
C6 | 0.1672 (2) | 0.8023 (7) | 0.3840 (6) | 0.0890 (17) | |
H6A | 0.1292 | 0.8373 | 0.3957 | 0.134* | |
H6B | 0.1929 | 0.8859 | 0.3852 | 0.134* | |
H6C | 0.1795 | 0.7362 | 0.4698 | 0.134* | |
C7 | 0.2272 (2) | 0.6627 (6) | 0.2058 (7) | 0.0811 (15) | |
H7A | 0.2266 | 0.6106 | 0.1069 | 0.122* | |
H7B | 0.2398 | 0.5962 | 0.2910 | 0.122* | |
H7C | 0.2530 | 0.7460 | 0.2063 | 0.122* | |
S2 | 0.05302 (4) | 0.26497 (11) | 0.17973 (16) | 0.0618 (4) | |
S3 | 0.05722 (4) | 0.60354 (12) | 0.15865 (16) | 0.0647 (4) | |
O1 | 0.14523 (17) | 0.4707 (5) | 0.3048 (8) | 0.152 (3) | |
S1 | 0.0000 | −0.0231 (2) | 0.2500 | 0.1387 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.048 (3) | 0.033 (3) | 0.130 (6) | 0.000 | 0.017 (3) | 0.000 |
C2 | 0.0348 (16) | 0.0334 (17) | 0.058 (2) | −0.0020 (13) | −0.0034 (15) | 0.0007 (15) |
C3 | 0.045 (2) | 0.051 (2) | 0.078 (3) | −0.0086 (18) | −0.0085 (19) | 0.020 (2) |
C4 | 0.047 (2) | 0.046 (2) | 0.058 (2) | −0.0109 (16) | 0.0067 (17) | 0.0011 (17) |
C5 | 0.062 (3) | 0.057 (3) | 0.089 (3) | −0.014 (2) | 0.009 (2) | 0.016 (2) |
C6 | 0.091 (4) | 0.101 (4) | 0.077 (3) | −0.033 (3) | 0.022 (3) | −0.028 (3) |
C7 | 0.052 (2) | 0.079 (3) | 0.113 (4) | −0.002 (2) | 0.013 (3) | 0.005 (3) |
S2 | 0.0440 (6) | 0.0395 (6) | 0.1045 (10) | 0.0010 (4) | 0.0205 (5) | −0.0066 (5) |
S3 | 0.0429 (6) | 0.0471 (6) | 0.1010 (9) | −0.0067 (4) | −0.0079 (5) | 0.0258 (6) |
O1 | 0.069 (2) | 0.096 (3) | 0.275 (7) | −0.029 (2) | −0.056 (3) | 0.106 (4) |
S1 | 0.0830 (14) | 0.0311 (9) | 0.311 (4) | 0.000 | 0.064 (2) | 0.000 |
Geometric parameters (Å, º) top
C1—S1 | 1.627 (6) | C4—C6 | 1.530 (6) |
C1—S2i | 1.721 (3) | C5—H5A | 0.9600 |
C1—S2 | 1.721 (3) | C5—H5B | 0.9600 |
C2—C2i | 1.344 (7) | C5—H5C | 0.9600 |
C2—S2 | 1.739 (4) | C6—H6A | 0.9600 |
C2—S3 | 1.748 (4) | C6—H6B | 0.9600 |
C3—O1 | 1.185 (5) | C6—H6C | 0.9600 |
C3—C4 | 1.517 (5) | C7—H7A | 0.9600 |
C3—S3 | 1.774 (4) | C7—H7B | 0.9600 |
C4—C5 | 1.514 (6) | C7—H7C | 0.9600 |
C4—C7 | 1.521 (6) | | |
| | | |
S1—C1—S2i | 123.58 (16) | C4—C5—H5C | 109.5 |
S1—C1—S2 | 123.58 (16) | H5A—C5—H5C | 109.5 |
S2i—C1—S2 | 112.8 (3) | H5B—C5—H5C | 109.5 |
C2i—C2—S2 | 115.99 (12) | C4—C6—H6A | 109.5 |
C2i—C2—S3 | 122.57 (13) | C4—C6—H6B | 109.5 |
S2—C2—S3 | 121.2 (2) | H6A—C6—H6B | 109.5 |
O1—C3—C4 | 123.9 (4) | C4—C6—H6C | 109.5 |
O1—C3—S3 | 120.7 (3) | H6A—C6—H6C | 109.5 |
C4—C3—S3 | 115.4 (3) | H6B—C6—H6C | 109.5 |
C5—C4—C3 | 113.3 (3) | C4—C7—H7A | 109.5 |
C5—C4—C7 | 109.5 (4) | C4—C7—H7B | 109.5 |
C3—C4—C7 | 107.7 (4) | H7A—C7—H7B | 109.5 |
C5—C4—C6 | 110.6 (4) | C4—C7—H7C | 109.5 |
C3—C4—C6 | 105.4 (4) | H7A—C7—H7C | 109.5 |
C7—C4—C6 | 110.3 (4) | H7B—C7—H7C | 109.5 |
C4—C5—H5A | 109.5 | C1—S2—C2 | 97.6 (2) |
C4—C5—H5B | 109.5 | C2—S3—C3 | 102.94 (17) |
H5A—C5—H5B | 109.5 | | |
| | | |
O1—C3—C4—C5 | 156.0 (6) | S2i—C1—S2—C2 | 0.17 (12) |
S3—C3—C4—C5 | −24.6 (5) | C2i—C2—S2—C1 | −0.6 (4) |
O1—C3—C4—C7 | 34.7 (7) | S3—C2—S2—C1 | −175.4 (2) |
S3—C3—C4—C7 | −145.8 (4) | C2i—C2—S3—C3 | 132.2 (5) |
O1—C3—C4—C6 | −83.0 (7) | S2—C2—S3—C3 | −53.3 (3) |
S3—C3—C4—C6 | 96.4 (4) | O1—C3—S3—C2 | 6.3 (6) |
S1—C1—S2—C2 | −179.83 (12) | C4—C3—S3—C2 | −173.1 (3) |
Symmetry code: (i) −x, y, −z+1/2. |
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