2-Methyl-sulfanyl-5,6-dihydro-2H-1,3-dithiolo[4,5-b][1,4]dioxin-2-ium tetra-fluoro-borate.

The title compound, C(6)H(7)O(2)S(3) (+)·BF(4) (-), consists of a planar 2-thioxo-1,3-dithiol-4,5-yl unit [maximum deviation from the ring plane = 0.020 (3) Å], with an ethyl-enedi-oxy group fused at the 4,5-positions; the ethyl-enedi-oxy C atoms are disordered over two positions with site-occupancy factors of 0.5. The 1,4-dioxine ring has a twist-chair conformation. Weak cation-anion S⋯F inter-actions [3.022 (4)-3.095 (4) Å] and an S⋯O [3.247 (4) Å] inter-action are present.

Related literature

For background on metal–organic coordination compounds, see: Chen et al. (2000 ▶); Xiong et al. (1999 ▶). For the preparation and crystal structure of a related compound, see: Han & Zhang (2010 ▶); Kanchanadevi et al. (2010 ▶).

Experimental

Crystal data

C6H7O2S3 +·BF4 −

M = 294.14

Monoclinic,

a = 10.7410 (13) Å

b = 10.1175 (10) Å

c = 10.1874 (11) Å

β = 94.488 (4)°

V = 1103.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.71 mm−1

T = 223 K

0.40 × 0.35 × 0.35 mm

Data collection

Rigaku Saturn CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.593, T max = 0.781

6014 measured reflections

2046 independent reflections

1749 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.174

S = 1.07

2046 reflections

147 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.55 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005326/rk2328sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005326/rk2328Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005326/rk2328Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H7O2S3+·BF4−	F(000) = 592
Mr = 294.14	Dx = 1.770 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 2895 reflections
a = 10.7410 (13) Å	θ = 3.3–27.5°
b = 10.1175 (10) Å	µ = 0.71 mm−1
c = 10.1874 (11) Å	T = 223 K
β = 94.488 (4)°	Block, yellow
V = 1103.7 (2) Å3	0.40 × 0.35 × 0.35 mm
Z = 4

Rigaku Saturn CCD diffractometer	2046 independent reflections
Radiation source: fine-focus sealed tube	1749 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 14.63 pixels mm-1	θmax = 25.5°, θmin = 3.3°
ω–scan	h = −12→13
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −10→12
Tmin = 0.593, Tmax = 0.781	l = −11→12
6014 measured reflections

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0986P)2 + 1.5661P] where P = (Fo2 + 2Fc2)/3
2046 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.69 e Å−3
6 restraints	Δρmin = −0.55 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	Occ. (<1)
S1	0.15907 (11)	0.25827 (11)	0.56191 (12)	0.0482 (4)
S2	0.26927 (10)	0.49599 (10)	0.46964 (11)	0.0428 (3)
S3	0.02403 (10)	0.39889 (11)	0.34288 (10)	0.0439 (3)
F1	0.1210 (3)	0.8199 (4)	0.4652 (3)	0.0815 (11)
F2	0.3311 (4)	0.7944 (4)	0.4588 (5)	0.1015 (14)
F3	0.2587 (4)	0.9828 (4)	0.5236 (5)	0.0953 (13)
F4	0.2242 (5)	0.9251 (8)	0.3140 (4)	0.161 (3)
O1	0.3475 (3)	0.2304 (3)	0.7435 (3)	0.0566 (9)
O2	0.4604 (3)	0.4681 (3)	0.6479 (3)	0.0528 (8)
C1	0.1508 (4)	0.3871 (4)	0.4559 (4)	0.0368 (9)
C2	0.3004 (4)	0.3043 (4)	0.6403 (4)	0.0427 (10)
C3	0.3528 (4)	0.4142 (4)	0.5960 (4)	0.0388 (9)
C4	0.4786 (15)	0.2727 (17)	0.7661 (15)	0.083 (3)	0.50
H4A	0.5251	0.2454	0.6916	0.099*	0.50
H4B	0.5169	0.2303	0.8457	0.099*	0.50
C4'	0.4634 (16)	0.2771 (19)	0.8065 (15)	0.083 (3)	0.50
H4'1	0.5278	0.2114	0.7917	0.099*	0.50
H4'2	0.4548	0.2801	0.9015	0.099*	0.50
C5	0.486 (2)	0.4194 (17)	0.7811 (18)	0.083 (3)	0.50
H5A	0.4229	0.4514	0.8384	0.099*	0.50
H5B	0.5686	0.4469	0.8179	0.099*	0.50
C5'	0.509 (2)	0.4054 (18)	0.7666 (19)	0.083 (3)	0.50
H5'1	0.4964	0.4670	0.8387	0.099*	0.50
H5'2	0.5991	0.3969	0.7616	0.099*	0.50
C6	0.0632 (5)	0.5445 (5)	0.2538 (5)	0.0603 (13)
H6A	0.0631	0.6207	0.3117	0.091*
H6B	0.0021	0.5575	0.1797	0.091*
H6C	0.1454	0.5340	0.2221	0.091*
B1	0.2316 (5)	0.8787 (6)	0.4366 (6)	0.0508 (13)

	U11	U22	U33	U12	U13	U23
S1	0.0445 (7)	0.0429 (6)	0.0560 (7)	−0.0110 (4)	−0.0040 (5)	0.0114 (5)
S2	0.0417 (6)	0.0382 (6)	0.0480 (6)	−0.0064 (4)	0.0010 (5)	0.0072 (4)
S3	0.0439 (6)	0.0461 (6)	0.0408 (6)	0.0008 (5)	−0.0032 (5)	−0.0037 (4)
F1	0.059 (2)	0.108 (3)	0.078 (2)	−0.0333 (19)	0.0133 (17)	−0.009 (2)
F2	0.073 (3)	0.079 (2)	0.152 (4)	0.0122 (19)	0.008 (3)	−0.008 (2)
F3	0.090 (3)	0.071 (2)	0.125 (3)	−0.0072 (19)	0.005 (2)	−0.028 (2)
F4	0.094 (3)	0.311 (8)	0.073 (3)	−0.079 (4)	−0.022 (2)	0.071 (4)
O1	0.051 (2)	0.058 (2)	0.059 (2)	−0.0042 (15)	−0.0088 (16)	0.0206 (16)
O2	0.0385 (17)	0.061 (2)	0.0575 (19)	−0.0113 (15)	−0.0048 (15)	0.0072 (15)
C1	0.039 (2)	0.033 (2)	0.038 (2)	0.0008 (16)	0.0050 (17)	−0.0016 (15)
C2	0.042 (2)	0.042 (2)	0.044 (2)	−0.0021 (18)	0.0020 (18)	0.0048 (18)
C3	0.033 (2)	0.041 (2)	0.042 (2)	−0.0013 (16)	−0.0003 (17)	0.0028 (17)
C4	0.074 (5)	0.097 (4)	0.071 (5)	−0.025 (3)	−0.029 (4)	0.035 (3)
C4'	0.074 (5)	0.097 (4)	0.071 (5)	−0.025 (3)	−0.029 (4)	0.035 (3)
C5	0.074 (5)	0.097 (4)	0.071 (5)	−0.025 (3)	−0.029 (4)	0.035 (3)
C5'	0.074 (5)	0.097 (4)	0.071 (5)	−0.025 (3)	−0.029 (4)	0.035 (3)
C6	0.069 (3)	0.057 (3)	0.054 (3)	0.007 (3)	−0.007 (2)	0.013 (2)
B1	0.044 (3)	0.054 (3)	0.055 (3)	−0.005 (2)	0.003 (2)	−0.002 (2)

S1—C1	1.691 (4)	O2—C5	1.450 (15)
S1—C2	1.723 (5)	C2—C3	1.341 (6)
S2—C1	1.681 (4)	C4—C5	1.493 (18)
S2—C3	1.723 (4)	C4—H4A	0.9800
S3—C1	1.717 (4)	C4—H4B	0.9800
S3—C6	1.797 (5)	C4'—C5'	1.456 (16)
F1—B1	1.379 (6)	C4'—H4'1	0.9800
F2—B1	1.373 (7)	C4'—H4'2	0.9800
F3—B1	1.392 (7)	C5—H5A	0.9800
F4—B1	1.332 (7)	C5—H5B	0.9800
O1—C2	1.356 (5)	C5'—H5'1	0.9800
O1—C4'	1.435 (13)	C5'—H5'2	0.9800
O1—C4	1.473 (14)	C6—H6A	0.9700
O2—C3	1.347 (5)	C6—H6B	0.9700
O2—C5'	1.427 (15)	C6—H6C	0.9700
C1—S1—C2	95.1 (2)	O1—C4'—H4'2	107.9
C1—S2—C3	95.4 (2)	C5'—C4'—H4'2	107.9
C1—S3—C6	101.0 (2)	H4'1—C4'—H4'2	107.2
C2—O1—C4'	115.0 (6)	O2—C5—C4	103.7 (14)
C2—O1—C4	104.8 (6)	O2—C5—H5A	111.0
C4'—O1—C4	18.0 (12)	C4—C5—H5A	111.0
C3—O2—C5'	113.3 (9)	O2—C5—H5B	111.0
C3—O2—C5	108.7 (9)	C4—C5—H5B	111.0
C5'—O2—C5	13 (2)	H5A—C5—H5B	109.0
S2—C1—S1	116.8 (3)	O2—C5'—C4'	121.7 (15)
S2—C1—S3	124.5 (2)	O2—C5'—H5'1	106.9
S1—C1—S3	118.8 (2)	C4'—C5'—H5'1	106.9
C3—C2—O1	125.3 (4)	O2—C5'—H5'2	106.9
C3—C2—S1	116.5 (3)	C4'—C5'—H5'2	106.9
O1—C2—S1	118.2 (3)	H5'1—C5'—H5'2	106.7
C2—C3—O2	125.0 (4)	S3—C6—H6A	109.5
C2—C3—S2	116.2 (3)	S3—C6—H6B	109.5
O2—C3—S2	118.6 (3)	H6A—C6—H6B	109.5
O1—C4—C5	110.2 (18)	S3—C6—H6C	109.5
O1—C4—H4A	109.6	H6A—C6—H6C	109.5
C5—C4—H4A	109.6	H6B—C6—H6C	109.5
O1—C4—H4B	109.6	F4—B1—F2	111.2 (5)
C5—C4—H4B	109.6	F4—B1—F1	111.2 (5)
H4A—C4—H4B	108.1	F2—B1—F1	111.7 (5)
O1—C4'—C5'	117.8 (13)	F4—B1—F3	108.9 (5)
O1—C4'—H4'1	107.9	F2—B1—F3	104.1 (5)
C5'—C4'—H4'1	107.9	F1—B1—F3	109.4 (4)
C3—S2—C1—S1	1.2 (3)	C5'—O2—C3—C2	−6.9 (13)
C3—S2—C1—S3	−178.9 (3)	C5—O2—C3—C2	−20.1 (11)
C2—S1—C1—S2	−0.6 (3)	C5'—O2—C3—S2	168.9 (12)
C2—S1—C1—S3	179.5 (3)	C5—O2—C3—S2	155.7 (10)
C6—S3—C1—S2	2.2 (3)	C1—S2—C3—C2	−1.7 (4)
C6—S3—C1—S1	−177.9 (3)	C1—S2—C3—O2	−177.8 (3)
C4'—O1—C2—C3	−0.6 (12)	C2—O1—C4—C5	53.2 (14)
C4—O1—C2—C3	−16.3 (10)	C4'—O1—C4—C5	−74 (5)
C4'—O1—C2—S1	−178.1 (11)	C2—O1—C4'—C5'	8 (3)
C4—O1—C2—S1	166.1 (8)	C4—O1—C4'—C5'	67 (4)
C1—S1—C2—C3	−0.6 (4)	C3—O2—C5—C4	53.0 (19)
C1—S1—C2—O1	177.2 (4)	C5'—O2—C5—C4	−60 (6)
O1—C2—C3—O2	−0.1 (7)	O1—C4—C5—O2	−75 (2)
S1—C2—C3—O2	177.4 (3)	C3—O2—C5'—C4'	15 (3)
O1—C2—C3—S2	−176.0 (4)	C5—O2—C5'—C4'	87 (7)
S1—C2—C3—S2	1.5 (5)	O1—C4'—C5'—O2	−16 (4)