2-r-(4-Chloro-phen-yl)-6-c-phenyl-3,4,5,6-tetra-hydro-2H-thio-pyran-4-one 1-oxide.

The thio-pyran unit of the title mol-ecule, C(17)H(15)ClO(2)S, is in chair form. A crystallographic mirror plane bis-ects the mol-ecule, passing through the O=S and the opposite C=O atoms of the central ring, with statistical disorder of the Cl atom. The geometry around the S atom is tetra-hedral and the carbonyl C is planar. The 4-chloro-phenyl group at the 2 position and the phenyl ring at the 6 position have equatorial orientations. Inter-molecular C-H⋯O and C-H⋯Cl hydrogen bonds are found in the crystal structure. In addition, there is a short O⋯C inter-molecular contact [2.970 (5) Å].

Related literature

For a related crystal structure, see: Thiruvalluvar et al. (2007 ▶). For applications of sulfoxides, see: Contreras et al. (1998 ▶); Hutton et al. (2002 ▶); Okada & Tanaka (2002 ▶). For the conformational analysis of substituted thian-1-oxides, see: Freeman et al. (2001 ▶); Nagao et al. (1995 ▶). For the anti­microbial activity of aliphatic, aromatic and cyclic sulfoxides, see: Ansel et al. (2006 ▶); Ingold et al. (1999 ▶); Rouvier et al. (2004 ▶).

Experimental

Crystal data

C17H15ClO2S

M = 318.81

Orthorhombic,

a = 11.5195 (5) Å

b = 25.7589 (12) Å

c = 5.2248 (2) Å

V = 1550.35 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 296 (2) K

0.58 × 0.35 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.809, T max = 0.945

33450 measured reflections

1954 independent reflections

1551 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.211

S = 1.20

1954 reflections

106 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT-NT (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037355/hg2443sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037355/hg2443Isup2.hkl

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

C17H15ClO2S	Dx = 1.366 Mg m−3
Mr = 318.81	Melting point: 417 K
Orthorhombic, Pnma	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 9562 reflections
a = 11.5195 (5) Å	θ = 3.0–24.8º
b = 25.7589 (12) Å	µ = 0.38 mm−1
c = 5.2248 (2) Å	T = 296 (2) K
V = 1550.35 (12) Å3	Thick, colourless
Z = 4	0.58 × 0.35 × 0.15 mm
F000 = 664

Bruker APEXII CCD diffractometer	1954 independent reflections
Radiation source: fine-focus sealed tube	1551 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.040
Detector resolution: 0 pixels mm-1	θmax = 28.3º
T = 296(2) K	θmin = 1.6º
φ and ω scans	h = −15→15
Absorption correction: multi-scan(SADABS; Bruker, 2004)	k = −34→34
Tmin = 0.809, Tmax = 0.945	l = −6→6
33450 measured reflections

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) = 0.211	w = 1/[σ2(Fo2) + (0.0825P)2 + 1.5305P] where P = (Fo2 + 2Fc2)/3
S = 1.20	(Δ/σ)max = 0.001
1954 reflections	Δρmax = 0.32 e Å−3
106 parameters	Δρmin = −0.42 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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)
Cl1	0.0955 (4)	0.00160 (11)	0.0431 (9)	0.1475 (18)	0.500
S1	0.24636 (8)	0.25000	0.27287 (17)	0.0434 (3)
O1	0.3171 (3)	0.25000	0.0330 (5)	0.0614 (10)
O4	0.5597 (3)	0.25000	0.7542 (7)	0.0772 (13)
C2	0.3029 (3)	0.19728 (12)	0.4726 (5)	0.0477 (9)
C3	0.4354 (3)	0.20065 (15)	0.4859 (7)	0.0621 (13)
C4	0.4819 (3)	0.25000	0.5959 (8)	0.0581 (16)
C11	0.2583 (3)	0.14695 (14)	0.3651 (7)	0.0593 (11)
C12	0.1618 (4)	0.12411 (19)	0.4657 (10)	0.0873 (18)
C13	0.1167 (5)	0.0784 (2)	0.3692 (16)	0.113 (3)
C14A	0.1685 (7)	0.0557 (2)	0.1666 (16)	0.112 (3)	0.500
C14B	0.1685 (7)	0.0557 (2)	0.1666 (16)	0.112 (3)	0.500
C15	0.2634 (7)	0.0778 (3)	0.0566 (14)	0.124 (3)
C16	0.3087 (5)	0.1234 (2)	0.1524 (10)	0.0940 (19)
H2	0.27192	0.20147	0.64603	0.0573*
H3A	0.46377	0.17188	0.58808	0.0745*
H3B	0.46629	0.19651	0.31439	0.0745*
H12	0.12502	0.13981	0.60394	0.1053*
H13	0.05139	0.06340	0.44321	0.1358*
H14B	0.13910	0.02476	0.10157	0.1344*	0.500
H15	0.29807	0.06199	−0.08411	0.1492*
H16	0.37304	0.13854	0.07466	0.1130*

	U11	U22	U33	U12	U13	U23
Cl1	0.168 (3)	0.0895 (18)	0.185 (4)	−0.0163 (19)	−0.060 (3)	−0.035 (2)
S1	0.0328 (5)	0.0708 (7)	0.0265 (5)	0.0000	−0.0033 (3)	0.0000
O1	0.0611 (19)	0.101 (2)	0.0221 (13)	0.0000	0.0046 (13)	0.0000
O4	0.0365 (16)	0.138 (3)	0.057 (2)	0.0000	−0.0168 (14)	0.0000
C2	0.0413 (14)	0.0715 (18)	0.0304 (13)	0.0054 (13)	−0.0019 (11)	0.0014 (12)
C3	0.0390 (15)	0.096 (3)	0.0512 (18)	0.0139 (16)	−0.0103 (13)	−0.0018 (17)
C4	0.0304 (19)	0.106 (4)	0.038 (2)	0.0000	−0.0045 (16)	0.0000
C11	0.0562 (18)	0.069 (2)	0.0527 (18)	0.0096 (16)	−0.0125 (15)	0.0000 (15)
C12	0.063 (2)	0.095 (3)	0.104 (4)	−0.007 (2)	0.009 (2)	−0.018 (3)
C13	0.092 (4)	0.097 (4)	0.150 (6)	−0.019 (3)	−0.005 (4)	−0.004 (4)
C14A	0.118 (5)	0.080 (3)	0.138 (5)	−0.001 (3)	−0.048 (4)	−0.017 (3)
C14B	0.118 (5)	0.080 (3)	0.138 (5)	−0.001 (3)	−0.048 (4)	−0.017 (3)
C15	0.156 (6)	0.099 (4)	0.118 (5)	0.008 (4)	−0.006 (4)	−0.045 (4)
C16	0.111 (4)	0.094 (3)	0.077 (3)	−0.001 (3)	0.013 (3)	−0.025 (3)

Cl1—C14A	1.751 (7)	C13—C14B	1.349 (11)
Cl1—C14B	1.751 (7)	C14A—C15	1.360 (11)
Cl1—H14B	0.8400	C14B—C15	1.360 (11)
S1—C2	1.832 (3)	C15—C16	1.379 (9)
S1—C2i	1.832 (3)	C2—H2	0.9800
S1—O1	1.495 (3)	C3—H3A	0.9700
O4—C4	1.220 (5)	C3—H3B	0.9700
C2—C3	1.530 (5)	C12—H12	0.9300
C2—C11	1.503 (5)	C13—H13	0.9300
C3—C4	1.494 (4)	C14A—H14B	0.9300
C11—C12	1.363 (6)	C14B—H14B	0.9300
C11—C16	1.393 (6)	C15—H15	0.9300
C12—C13	1.382 (8)	C16—H16	0.9300
C13—C14A	1.349 (11)
Cl1···C15ii	3.645 (9)	C2···O1xiv	3.232 (4)
Cl1···H15iii	2.8200	C2···O1x	3.232 (4)
S1···O4iv	3.494 (4)	C3···O1xiv	3.412 (4)
S1···O4v	3.276 (4)	C3···O1x	3.412 (4)
S1···C4iv	3.605 (4)	C4···S1xii	3.605 (4)
S1···O4vi	3.494 (4)	C4···O1xiv	2.970 (5)
S1···O4vii	3.276 (4)	C4···S1xv	3.605 (4)
S1···C4vi	3.605 (4)	C4···O1x	2.970 (5)
O1···O4viii	3.152 (5)	C12···C15xiv	3.511 (9)
O1···C2viii	3.232 (4)	C15···C12viii	3.511 (9)
O1···C3viii	3.412 (4)	C15···Cl1iii	3.645 (9)
O1···C4viii	2.970 (5)	C16···O1	3.322 (5)
O1···C16	3.322 (5)	C3···H16	2.7700
O1···C2ix	3.232 (4)	C16···H3B	2.7500
O1···C3ix	3.412 (4)	H2···O1xiv	2.4300
O1···O4ix	3.152 (5)	H2···H12	2.3300
O1···C16i	3.322 (5)	H2···O4v	2.7900
O1···C4ix	2.970 (5)	H2···O4vii	2.7900
O4···O1x	3.152 (5)	H2···O1x	2.4300
O4···S1xi	3.276 (4)	H2···H2i	2.5000
O4···S1xii	3.494 (4)	H3A···H12xi	2.5900
O4···S1xiii	3.276 (4)	H3B···O1	2.6500
O4···O1xiv	3.152 (5)	H3B···C16	2.7500
O4···S1xv	3.494 (4)	H3B···H16	2.2300
O1···H3Bi	2.6500	H12···H2	2.3300
O1···H2viii	2.4300	H12···H3Avii	2.5900
O1···H2ix	2.4300	H15···Cl1ii	2.8200
O1···H3B	2.6500	H16···C3	2.7700
O4···H2xiii	2.7900	H16···H3B	2.2300
O4···H2xi	2.7900
C14A—Cl1—H14B	8.00	C11—C16—C15	120.2 (5)
C14B—Cl1—H14B	8.00	S1—C2—H2	108.00
C2—S1—C2i	95.66 (14)	C3—C2—H2	108.00
O1—S1—C2	106.48 (13)	C11—C2—H2	108.00
O1—S1—C2i	106.48 (13)	C2—C3—H3A	109.00
C3—C2—C11	114.0 (3)	C2—C3—H3B	109.00
S1—C2—C3	109.8 (2)	C4—C3—H3A	109.00
S1—C2—C11	107.8 (2)	C4—C3—H3B	108.00
C2—C3—C4	115.0 (3)	H3A—C3—H3B	108.00
C3—C4—C3i	116.6 (3)	C11—C12—H12	119.00
O4—C4—C3	121.62 (19)	C13—C12—H12	119.00
O4—C4—C3i	121.62 (19)	C12—C13—H13	120.00
C12—C11—C16	117.4 (4)	C14A—C13—H13	120.00
C2—C11—C16	122.1 (4)	C14B—C13—H13	120.00
C2—C11—C12	120.5 (3)	Cl1—C14A—H14B	8.00
C11—C12—C13	122.2 (5)	C13—C14A—H14B	120.00
C12—C13—C14A	119.3 (6)	C15—C14A—H14B	120.00
C12—C13—C14B	119.3 (6)	Cl1—C14B—H14B	8.00
Cl1—C14A—C15	124.3 (6)	C13—C14B—H14B	120.00
Cl1—C14A—C13	115.0 (6)	C15—C14B—H14B	120.00
C13—C14A—C15	120.4 (6)	C14A—C15—H15	120.00
Cl1—C14B—C15	124.3 (6)	C14B—C15—H15	120.00
C13—C14B—C15	120.4 (6)	C16—C15—H15	120.00
Cl1—C14B—C13	115.0 (6)	C11—C16—H16	120.00
C14A—C15—C16	120.5 (7)	C15—C16—H16	120.00
C14B—C15—C16	120.5 (7)
O1—S1—C2—C3	48.2 (2)	C2—C11—C16—C15	−178.6 (5)
O1—S1—C2—C11	−76.5 (2)	C12—C11—C16—C15	−2.2 (7)
C2i—S1—C2—C3	−60.9 (2)	C11—C12—C13—C14A	−0.9 (9)
C2i—S1—C2—C11	174.5 (2)	C11—C12—C13—C14B	−0.9 (9)
S1—C2—C3—C4	59.9 (3)	C12—C13—C14A—Cl1	−174.1 (5)
C11—C2—C3—C4	−179.1 (3)	C12—C13—C14A—C15	−0.7 (11)
S1—C2—C11—C12	−96.7 (4)	C12—C13—C14B—Cl1	−174.1 (5)
S1—C2—C11—C16	79.6 (4)	C12—C13—C14B—C15	−0.7 (11)
C3—C2—C11—C12	141.3 (4)	Cl1—C14A—C15—C16	173.5 (6)
C3—C2—C11—C16	−42.5 (5)	C13—C14A—C15—C16	0.7 (11)
C2—C3—C4—O4	134.6 (4)	Cl1—C14B—C15—C16	173.5 (6)
C2—C3—C4—C3i	−50.5 (4)	C13—C14B—C15—C16	0.7 (11)
C2—C11—C12—C13	178.7 (5)	C14A—C15—C16—C11	0.8 (10)
C16—C11—C12—C13	2.3 (7)	C14B—C15—C16—C11	0.8 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1xiv	0.98	2.43	3.232 (4)	138
C15—H15···Cl1ii	0.93	2.82	3.745 (9)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.98	2.43	3.232 (4)	138
C15—H15⋯Cl1ii	0.93	2.82	3.745 (9)	170

Symmetry codes: (i) ; (ii) .