(1RS,3RS)-2-Methoxy­methyl-1,3-di­thiol­ane 1,3-dioxide

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.

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

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)

Crystal data

C5H10O3S2	F(000) = 384
Mr = 182.27	Dx = 1.498 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 14.4429 (19) Å	θ = 10–18°
b = 6.3787 (8) Å	µ = 0.61 mm^−1
c = 8.8867 (10) Å	T = 293 K
β = 99.260 (14)°	Rod shaped, colourless
V = 808.04 (17) Å^3	0.35 × 0.20 × 0.10 mm
Z = 4

Data collection

Siemens P4 Diffractometer	Rint = 0.044
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 1.4°
Graphite monochromator	h = −16→17
non–profiled w–scans	k = −7→7
1666 measured reflections	l = −1→10
1589 independent reflections	2 standard reflections every 50 reflections
1033 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0733P)^2 + 0.5976P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1161 reflections	Δρmax = 0.38 e Å^−3
112 parameters	Δρmin = −0.48 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.074 (8)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
H41	0.315 (3)	−0.246 (7)	0.377 (5)	0.066 (12)*
H1	0.286 (2)	−0.019 (5)	0.101 (4)	0.037 (8)*
H21	0.145 (2)	0.286 (5)	0.141 (4)	0.043 (9)*
H22	0.124 (2)	0.335 (6)	0.304 (4)	0.049 (10)*
H42	0.332 (3)	−0.341 (7)	0.223 (4)	0.063 (12)*
S1	0.26249 (5)	0.17257 (12)	0.32168 (9)	0.0399 (4)
S2	0.14547 (6)	−0.16820 (12)	0.14049 (9)	0.0407 (4)
O2	0.12296 (18)	−0.1164 (4)	−0.0258 (2)	0.0544 (7)
O1	0.25977 (18)	0.0965 (4)	0.4804 (2)	0.0553 (7)
O3	0.42013 (16)	−0.1273 (4)	0.3048 (3)	0.0569 (7)
C2	0.1429 (2)	0.2279 (6)	0.2396 (4)	0.0427 (8)
C3	0.0895 (2)	0.0274 (6)	0.2408 (4)	0.0452 (8)
H3A	0.0251	0.0474	0.1915	0.054*
H3B	0.0889	−0.0174	0.3449	0.054*
C4	0.3306 (2)	−0.2208 (6)	0.2822 (4)	0.0469 (9)
C1	0.2636 (2)	−0.0610 (5)	0.2027 (3)	0.0359 (8)
C5	0.4889 (3)	−0.2472 (8)	0.4002 (5)	0.0754 (13)
H5A	0.5481	−0.1757	0.4119	0.113*
H5B	0.4948	−0.3822	0.3549	0.113*
H5C	0.4702	−0.2648	0.4983	0.113*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0408 (6)	0.0381 (6)	0.0394 (6)	−0.0030 (3)	0.0024 (4)	−0.0085 (3)
S2	0.0503 (6)	0.0349 (6)	0.0330 (6)	−0.0060 (3)	−0.0047 (4)	0.0005 (3)
O2	0.0732 (16)	0.0591 (15)	0.0258 (12)	−0.0011 (13)	−0.0081 (11)	−0.0015 (11)
O1	0.0619 (15)	0.0732 (17)	0.0281 (12)	0.0093 (13)	−0.0008 (10)	−0.0083 (11)
O3	0.0439 (13)	0.0602 (16)	0.0653 (16)	0.0097 (12)	0.0050 (11)	0.0107 (13)
C2	0.0493 (19)	0.0423 (18)	0.0362 (18)	0.0064 (15)	0.0055 (15)	0.0016 (15)
C3	0.0393 (17)	0.059 (2)	0.0366 (17)	−0.0004 (15)	0.0035 (13)	0.0026 (15)
C4	0.052 (2)	0.0435 (19)	0.044 (2)	0.0058 (16)	0.0055 (16)	0.0033 (17)
C1	0.0413 (16)	0.0387 (18)	0.0272 (14)	0.0004 (13)	0.0041 (12)	−0.0035 (12)
C5	0.061 (3)	0.082 (3)	0.078 (3)	0.028 (2)	−0.007 (2)	0.004 (3)

Geometric parameters (Å, º)

S1—O1	1.499 (2)	C2—H22	0.96 (4)
S1—C2	1.798 (3)	C3—H3A	0.9700
S1—C1	1.828 (3)	C3—H3B	0.9700
S2—O2	1.498 (2)	C4—C1	1.502 (5)
S2—C3	1.799 (3)	C4—H41	0.92 (4)
S2—C1	1.839 (3)	C4—H42	0.93 (4)
O3—C4	1.409 (4)	C1—H1	1.04 (3)
O3—C5	1.421 (5)	C5—H5A	0.9600
C2—C3	1.494 (5)	C5—H5B	0.9600
C2—H21	0.96 (4)	C5—H5C	0.9600
O1—S1—C2	106.04 (15)	O3—C4—C1	106.6 (3)
O1—S1—C1	106.54 (14)	O3—C4—H41	108 (3)
C2—S1—C1	91.29 (15)	C1—C4—H41	108 (3)
O2—S2—C3	107.00 (15)	O3—C4—H42	109 (2)
O2—S2—C1	104.96 (14)	C1—C4—H42	111 (2)
C3—S2—C1	93.57 (14)	H41—C4—H42	113 (4)
C4—O3—C5	113.2 (3)	C4—C1—S1	110.2 (2)
C3—C2—S1	107.0 (2)	C4—C1—S2	112.7 (2)
C3—C2—H21	115 (2)	S1—C1—S2	112.51 (16)
S1—C2—H21	106.4 (19)	C4—C1—H1	108.5 (17)
C3—C2—H22	114 (2)	S1—C1—H1	109.0 (17)
S1—C2—H22	104 (2)	S2—C1—H1	103.6 (17)
H21—C2—H22	109 (3)	O3—C5—H5A	109.5
C2—C3—S2	108.4 (2)	O3—C5—H5B	109.5
C2—C3—H3A	110.0	H5A—C5—H5B	109.5
S2—C3—H3A	110.0	O3—C5—H5C	109.5
C2—C3—H3B	110.0	H5A—C5—H5C	109.5
S2—C3—H3B	110.0	H5B—C5—H5C	109.5
H3A—C3—H3B	108.4
O1—S1—C2—C3	−60.2 (3)	O1—S1—C1—C4	−43.8 (3)
C1—S1—C2—C3	47.4 (2)	C2—S1—C1—C4	−151.0 (3)
S1—C2—C3—S2	−56.1 (3)	O1—S1—C1—S2	82.86 (18)
O2—S2—C3—C2	−73.5 (2)	C2—S1—C1—S2	−24.30 (19)
C1—S2—C3—C2	33.3 (2)	O2—S2—C1—C4	−126.9 (3)
C5—O3—C4—C1	170.7 (3)	C3—S2—C1—C4	124.4 (3)
O3—C4—C1—S1	−61.2 (3)	O2—S2—C1—S1	107.70 (18)
O3—C4—C1—S2	172.2 (2)	C3—S2—C1—S1	−0.96 (19)