2-Chloro-methyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine.

In the mol-ecule of the title compound, C(7)H(7)ClO(2)S, the six-membered ring adopts a twisted conformation. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules. There is also a weak C-H⋯π inter-action.

Related literature

For a related structure, see: Jose et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C7H7ClO2S

M = 190.64

Monoclinic,

a = 10.227 (2) Å

b = 5.7500 (12) Å

c = 14.376 (3) Å

β = 105.55 (3)°

V = 814.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.67 mm−1

T = 294 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.825, T max = 0.936

1565 measured reflections

1479 independent reflections

1065 reflections with I > 2σ(I)

R int = 0.067

3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.185

S = 1.01

1479 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809007156/hk2630sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007156/hk2630Isup2.hkl

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

C7H7ClO2S	F(000) = 392
Mr = 190.64	Dx = 1.555 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 10.227 (2) Å	θ = 10–13°
b = 5.7500 (12) Å	µ = 0.67 mm−1
c = 14.376 (3) Å	T = 294 K
β = 105.55 (3)°	Block, colorless
V = 814.4 (3) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1065 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.067
graphite	θmax = 25.4°, θmin = 2.2°
ω/2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→6
Tmin = 0.825, Tmax = 0.936	l = −17→16
1565 measured reflections	3 standard reflections every 120 min
1479 independent reflections	intensity decay: 1%

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.1P)2 + 0.92P] where P = (Fo2 + 2Fc2)/3
1479 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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
Cl	−0.37084 (12)	0.1937 (2)	0.51615 (9)	0.0759 (5)
S	0.12047 (12)	0.1840 (2)	0.27636 (9)	0.0740 (5)
O1	−0.1425 (3)	0.6480 (5)	0.29741 (19)	0.0619 (8)
O2	−0.1277 (2)	0.2762 (4)	0.43358 (19)	0.0505 (7)
C1	−0.2959 (4)	0.4560 (8)	0.4923 (3)	0.0569 (10)
H1A	−0.3636	0.5786	0.4805	0.068*
H1B	−0.2238	0.4991	0.5486	0.068*
C2	−0.2397 (4)	0.4363 (7)	0.4079 (3)	0.0524 (9)
H2A	−0.3096	0.3729	0.3531	0.063*
C3	−0.1903 (4)	0.6650 (6)	0.3787 (3)	0.0539 (10)
H3A	−0.2641	0.7765	0.3663	0.065*
H3B	−0.1181	0.7236	0.4320	0.065*
C4	−0.0539 (4)	0.4634 (7)	0.3034 (3)	0.0515 (9)
C5	−0.0507 (4)	0.2828 (6)	0.3683 (3)	0.0477 (9)
C6	0.0309 (4)	0.4363 (8)	0.2481 (3)	0.0632 (11)
H6A	0.0400	0.5405	0.2008	0.076*
C7	0.0424 (4)	0.1179 (7)	0.3626 (3)	0.0591 (10)
H7A	0.0605	−0.0143	0.4012	0.071*

	U11	U22	U33	U12	U13	U23
Cl	0.0794 (8)	0.0787 (9)	0.0741 (8)	−0.0128 (6)	0.0285 (6)	−0.0007 (6)
S	0.0758 (8)	0.0812 (9)	0.0696 (8)	0.0012 (6)	0.0275 (6)	−0.0095 (6)
O1	0.0693 (18)	0.0601 (18)	0.0461 (16)	0.0112 (14)	−0.0024 (13)	0.0218 (13)
O2	0.0571 (15)	0.0440 (14)	0.0484 (15)	0.0044 (12)	0.0110 (12)	0.0090 (12)
C1	0.061 (2)	0.066 (3)	0.0370 (19)	−0.005 (2)	0.0014 (17)	−0.0062 (18)
C2	0.051 (2)	0.053 (2)	0.042 (2)	−0.0049 (17)	−0.0081 (16)	−0.0067 (17)
C3	0.068 (2)	0.047 (2)	0.040 (2)	0.0146 (18)	0.0034 (17)	0.0132 (17)
C4	0.055 (2)	0.057 (2)	0.0329 (18)	−0.0073 (18)	−0.0059 (16)	0.0042 (17)
C5	0.059 (2)	0.044 (2)	0.0355 (18)	−0.0114 (17)	0.0042 (15)	−0.0069 (16)
C6	0.069 (3)	0.073 (3)	0.044 (2)	−0.004 (2)	0.0078 (19)	0.006 (2)
C7	0.064 (2)	0.051 (2)	0.059 (2)	0.0111 (19)	0.012 (2)	0.001 (2)

Cl—C1	1.766 (4)	C2—C3	1.508 (5)
S—C7	1.688 (4)	C2—H2A	0.9800
S—C6	1.706 (5)	C3—H3A	0.9700
O1—C4	1.384 (5)	C3—H3B	0.9700
O1—C3	1.386 (5)	C4—C6	1.333 (5)
O2—C5	1.377 (5)	C4—C5	1.391 (5)
O2—C2	1.439 (5)	C5—C7	1.362 (5)
C1—C2	1.480 (5)	C6—H6A	0.9300
C1—H1A	0.9700	C7—H7A	0.9300
C1—H1B	0.9700
C7—S—C6	92.1 (2)	C2—C3—H3A	108.9
C4—O1—C3	112.0 (3)	O1—C3—H3B	108.9
C5—O2—C2	111.6 (3)	C2—C3—H3B	108.9
C2—C1—Cl	112.2 (3)	H3A—C3—H3B	107.8
C2—C1—H1A	109.2	C6—C4—O1	124.9 (4)
Cl—C1—H1A	109.2	C6—C4—C5	114.3 (4)
C2—C1—H1B	109.2	O1—C4—C5	120.8 (3)
Cl—C1—H1B	109.2	C7—C5—O2	124.0 (3)
H1A—C1—H1B	107.9	C7—C5—C4	111.7 (4)
O2—C2—C1	107.2 (3)	O2—C5—C4	124.3 (3)
O2—C2—C3	109.0 (3)	C4—C6—S	110.5 (3)
C1—C2—C3	113.2 (3)	C4—C6—H6A	124.7
O2—C2—H2A	109.1	S—C6—H6A	124.7
C1—C2—H2A	109.1	C5—C7—S	111.3 (3)
C3—C2—H2A	109.1	C5—C7—H7A	124.3
O1—C3—C2	113.2 (3)	S—C7—H7A	124.3
O1—C3—H3A	108.9
C5—O2—C2—C1	−167.2 (3)	C6—C4—C5—C7	1.5 (5)
C5—O2—C2—C3	−44.3 (4)	O1—C4—C5—C7	179.5 (3)
Cl—C1—C2—O2	−66.6 (3)	C6—C4—C5—O2	178.7 (3)
Cl—C1—C2—C3	173.1 (3)	O1—C4—C5—O2	−3.2 (5)
C4—O1—C3—C2	−48.0 (4)	O1—C4—C6—S	−178.8 (3)
O2—C2—C3—O1	63.1 (4)	C5—C4—C6—S	−0.8 (5)
C1—C2—C3—O1	−177.6 (3)	C7—S—C6—C4	0.0 (3)
C3—O1—C4—C6	−163.6 (4)	O2—C5—C7—S	−178.7 (3)
C3—O1—C4—C5	18.6 (5)	C4—C5—C7—S	−1.4 (4)
C2—O2—C5—C7	−165.2 (4)	C6—S—C7—C5	0.8 (3)
C2—O2—C5—C4	17.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1i	0.98	2.45	3.317 (5)	146
C1—H1B···Cg1ii	0.97	2.75	3.708 (5)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1i	0.98	2.45	3.317 (5)	146
C1—H1B⋯Cg1ii	0.97	2.75	3.708 (5)	168

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the S/C4–C7 ring.