Download citation
Download citation
link to html
The title compound, C5H10O3S2, consists of a five-membered di­thiol­ane ring with one O atom bonded to each S atom and a methoxy­methyl group at the 2-position. Some interatomic close contacts appear to influence the geometry of the di­thiol­ane ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019500/su6046sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019500/su6046Isup2.hkl
Contains datablock I

CCDC reference: 225781

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.044
  • wR factor = 0.129
  • Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.05 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: SHELXTL97 (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 publication routines (Farrugia, 1999).

(I) top
Crystal data top
C5H10O3S2F(000) = 384
Mr = 182.27Dx = 1.498 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 14.4429 (19) Åθ = 10–18°
b = 6.3787 (8) ŵ = 0.61 mm1
c = 8.8867 (10) ÅT = 293 K
β = 99.260 (14)°Rod shaped, colourless
V = 808.04 (17) Å30.35 × 0.20 × 0.10 mm
Z = 4
Data collection top
Siemens P4 DiffractometerRint = 0.044
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 1.4°
Graphite monochromatorh = 1617
non–profiled w–scansk = 77
1666 measured reflectionsl = 110
1589 independent reflections2 standard reflections every 50 reflections
1033 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.0733P)2 + 0.5976P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
1161 reflectionsΔρmax = 0.38 e Å3
112 parametersΔρmin = 0.48 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.074 (8)
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
xyzUiso*/Ueq
H410.315 (3)0.246 (7)0.377 (5)0.066 (12)*
H10.286 (2)0.019 (5)0.101 (4)0.037 (8)*
H210.145 (2)0.286 (5)0.141 (4)0.043 (9)*
H220.124 (2)0.335 (6)0.304 (4)0.049 (10)*
H420.332 (3)0.341 (7)0.223 (4)0.063 (12)*
S10.26249 (5)0.17257 (12)0.32168 (9)0.0399 (4)
S20.14547 (6)0.16820 (12)0.14049 (9)0.0407 (4)
O20.12296 (18)0.1164 (4)0.0258 (2)0.0544 (7)
O10.25977 (18)0.0965 (4)0.4804 (2)0.0553 (7)
O30.42013 (16)0.1273 (4)0.3048 (3)0.0569 (7)
C20.1429 (2)0.2279 (6)0.2396 (4)0.0427 (8)
C30.0895 (2)0.0274 (6)0.2408 (4)0.0452 (8)
H3A0.02510.04740.19150.054*
H3B0.08890.01740.34490.054*
C40.3306 (2)0.2208 (6)0.2822 (4)0.0469 (9)
C10.2636 (2)0.0610 (5)0.2027 (3)0.0359 (8)
C50.4889 (3)0.2472 (8)0.4002 (5)0.0754 (13)
H5A0.54810.17570.41190.113*
H5B0.49480.38220.35490.113*
H5C0.47020.26480.49830.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0408 (6)0.0381 (6)0.0394 (6)0.0030 (3)0.0024 (4)0.0085 (3)
S20.0503 (6)0.0349 (6)0.0330 (6)0.0060 (3)0.0047 (4)0.0005 (3)
O20.0732 (16)0.0591 (15)0.0258 (12)0.0011 (13)0.0081 (11)0.0015 (11)
O10.0619 (15)0.0732 (17)0.0281 (12)0.0093 (13)0.0008 (10)0.0083 (11)
O30.0439 (13)0.0602 (16)0.0653 (16)0.0097 (12)0.0050 (11)0.0107 (13)
C20.0493 (19)0.0423 (18)0.0362 (18)0.0064 (15)0.0055 (15)0.0016 (15)
C30.0393 (17)0.059 (2)0.0366 (17)0.0004 (15)0.0035 (13)0.0026 (15)
C40.052 (2)0.0435 (19)0.044 (2)0.0058 (16)0.0055 (16)0.0033 (17)
C10.0413 (16)0.0387 (18)0.0272 (14)0.0004 (13)0.0041 (12)0.0035 (12)
C50.061 (3)0.082 (3)0.078 (3)0.028 (2)0.007 (2)0.004 (3)
Geometric parameters (Å, º) top
S1—O11.499 (2)C2—H220.96 (4)
S1—C21.798 (3)C3—H3A0.9700
S1—C11.828 (3)C3—H3B0.9700
S2—O21.498 (2)C4—C11.502 (5)
S2—C31.799 (3)C4—H410.92 (4)
S2—C11.839 (3)C4—H420.93 (4)
O3—C41.409 (4)C1—H11.04 (3)
O3—C51.421 (5)C5—H5A0.9600
C2—C31.494 (5)C5—H5B0.9600
C2—H210.96 (4)C5—H5C0.9600
O1—S1—C2106.04 (15)O3—C4—C1106.6 (3)
O1—S1—C1106.54 (14)O3—C4—H41108 (3)
C2—S1—C191.29 (15)C1—C4—H41108 (3)
O2—S2—C3107.00 (15)O3—C4—H42109 (2)
O2—S2—C1104.96 (14)C1—C4—H42111 (2)
C3—S2—C193.57 (14)H41—C4—H42113 (4)
C4—O3—C5113.2 (3)C4—C1—S1110.2 (2)
C3—C2—S1107.0 (2)C4—C1—S2112.7 (2)
C3—C2—H21115 (2)S1—C1—S2112.51 (16)
S1—C2—H21106.4 (19)C4—C1—H1108.5 (17)
C3—C2—H22114 (2)S1—C1—H1109.0 (17)
S1—C2—H22104 (2)S2—C1—H1103.6 (17)
H21—C2—H22109 (3)O3—C5—H5A109.5
C2—C3—S2108.4 (2)O3—C5—H5B109.5
C2—C3—H3A110.0H5A—C5—H5B109.5
S2—C3—H3A110.0O3—C5—H5C109.5
C2—C3—H3B110.0H5A—C5—H5C109.5
S2—C3—H3B110.0H5B—C5—H5C109.5
H3A—C3—H3B108.4
O1—S1—C2—C360.2 (3)O1—S1—C1—C443.8 (3)
C1—S1—C2—C347.4 (2)C2—S1—C1—C4151.0 (3)
S1—C2—C3—S256.1 (3)O1—S1—C1—S282.86 (18)
O2—S2—C3—C273.5 (2)C2—S1—C1—S224.30 (19)
C1—S2—C3—C233.3 (2)O2—S2—C1—C4126.9 (3)
C5—O3—C4—C1170.7 (3)C3—S2—C1—C4124.4 (3)
O3—C4—C1—S161.2 (3)O2—S2—C1—S1107.70 (18)
O3—C4—C1—S2172.2 (2)C3—S2—C1—S10.96 (19)
Comparison of the bond angles (°) in the dithiolane ring of (I) with the corresponding values in the related compounds (II), (III), (IV), (V) and (VI). Note that s.u. values are not available for (VI) top
Angles(I)(II)(III)(IV)(V)(VI)
S1-C1-S2112.51 (16)105.83 (8)/106.20 (9)106.6 (4)106.93 (8)107.37 (9)112
C1-S1-C291.29 (15)98.60 (8)/97.80 (9)96.1 (5)94.6 (1)95.04 (9)94
C1-S2-C393.57 (14)99.74 (8)/99.81 (9)97.9 (5)98.4 (1)97.89 (9)92
S1-C2-C3107.0 (2)106.13 (12)/106.31 (13)111.7 (5)107.5 (2)109.0 (2)109
C2-C3-S2108.4 (2)105.61 (12)/107.96 (13)111.4 (5)109.7 (2)107.2 (1)106
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds