2-r-(4-Chloro­phen­yl)-6-c-phenyl-3,4,5,6-tetra­hydro-2H-thio­pyran-4-one 1-oxide

Thiruvalluvar, A.; Balamurugan, S.; Butcher, R.J.; Pandiarajan, K.; Devanathan, D.

doi:10.1107/S1600536808037355

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2367

doi:10.1107/S1600536808037355

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2-r-(4-Chlorophenyl)-6-c-phenyl-3,4,5,6-tetrahydro-2H-thiopyran-4-one 1-oxide

A. Thiruvalluvar,^a ^* S. Balamurugan,^a R. J. Butcher,^b K. Pandiarajan ^c and D. Devanathan ^c

^aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and ^cDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India
^*Correspondence e-mail: athiru@vsnl.net

(Received 10 November 2008; accepted 11 November 2008; online 20 November 2008)

The thiopyran unit of the title molecule, C₁₇H₁₅ClO₂S, is in chair form. A crystallographic mirror plane bisects the molecule, 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 tetrahedral and the carbonyl C is planar. The 4-chlorophenyl group at the 2 position and the phenyl ring at the 6 position have equatorial orientations. Intermolecular C—H⋯O and C—H⋯Cl hydrogen bonds are found in the crystal structure. In addition, there is a short O⋯C intermolecular 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_r = 318.81
Orthorhombic, P n m a
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[F² > 2σ(F²)] = 0.060
wR(F²) = 0.211
S = 1.20
1954 reflections
106 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.42 e Å⁻³

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) x, y, z+1; (ii) $[-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

Increasing interest has been focused on the stereochemical aspects of sulphoxides. The conformational analysis of cyclic sulphoxides is an area of attraction for many groups (Okada & Tanaka, 2002; Hutton et al., 2002; Contreras et al., 1998). Significant attention was earlier directed toward the conformational analysis of substituted thian-1-oxides (Freeman et al., 2001; Nagao et al., 1995). The conformational integrity of the sulphoxide has also generated interest in the various conditions under which it may undergo stereoisomerization. A large number of aliphatic, aromatic and cyclic sulphoxides exhibit antimicrobial activity (Ingold et al., 1999; Ansel et al., 2006; Rouvier et al., 2004). Although extensive studies on sulphoxides have disclosed their chemical and physico-chemical properties, little is known about the properties of the sulphinyl groups in cyclic sulphoxides. To investigate the conformations, substitution effect and antimicrobial activity of unsymmetrical thiopyran-4-one 1-oxides, the title compound was synthesized.

Thiruvalluvar et al., (2007) have reported a crystal structure of 2-(4-Fluorophenyl)-6-phenyltetrahydro-2H-thiopyran-4-one 1-oxide, wherein the thiopyran unit is in chair form. The molecular structure of the title compound, with atomic numbering scheme, is shown in Fig. 1. The thiopyran unit of the title molecule, C₁₇H₁₅ClO₂S, is in the chair form. The geometry around S1 atom is tetrahedral and C4 is planar. A crystallographic mirror plane bisects the molecule, passing through the O=S and the opposite C=O atoms of the central ring. The (p-chloro)phenyl at the 2 position and the phenyl ring at the 6 position have equatorial orientations. C2—H2···O1(x, y, 1 + z) and C15—H15···Cl1(1/2 - x, -y, -1/2 + z) intermolecular hydrogen bonds forming an infinite one dimensional chain with base vector [0 0 1] are found in the crystal structure. Further, a short intermolecular O1···C4(x, y, -1 + z) contact of 2.970 (5)Å is also found in the crystal structure.

Related literature top

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 top

A mixture of cis-2-(4-chlorophenyl)-6-phenyldithian-4-one (3.18 g, 0.01 mol), diethyl ether (60 ml), bromine (3.0 g) in water (30 ml) was shaken for few minutes. The solid that separated was filtered, washed with ether and recrystallized from chloroform-carbon tetrachloride mixture (1:1 v/v). The yield obtained was 68%(2.16 g).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); 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).

Figures top

	Fig. 1. The molecular structure of the title compound with the atomic numbering and 30% probability displacement ellipsoids. The unlabelled and labelled atoms are related by mirror plane [symmetry code: x, 1/2 - y, z].
	Fig. 2. The packing of the title compound, viewed down the c axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

2-r-(4-Chlorophenyl)-6-c-phenyl-3,4,5,6-tetrahydro-2H-thiopyran-4-one 1-oxide top

Crystal data top

C₁₇H₁₅ClO₂S	D_x = 1.366 Mg m⁻³
M_r = 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 = 3.0–24.8°
b = 25.7589 (12) Å	µ = 0.38 mm⁻¹
c = 5.2248 (2) Å	T = 296 K
V = 1550.35 (12) Å³	Thick, colourless
Z = 4	0.58 × 0.35 × 0.15 mm
F(000) = 664

Data collection top

Bruker APEXII CCD diffractometer	1954 independent reflections
Radiation source: fine-focus sealed tube	1551 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 0 pixels mm^-1	θ_max = 28.3°, θ_min = 1.6°
ϕ and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −34→34
T_min = 0.809, T_max = 0.945	l = −6→6
33450 measured reflections

Refinement top

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.211	H-atom parameters constrained
S = 1.20	w = 1/[σ²(F_o²) + (0.0825P)² + 1.5305P] where P = (F_o² + 2F_c²)/3
1954 reflections	(Δ/σ)_max = 0.001
106 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₇H₁₅ClO₂S	V = 1550.35 (12) Å³
M_r = 318.81	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 11.5195 (5) Å	µ = 0.38 mm⁻¹
b = 25.7589 (12) Å	T = 296 K
c = 5.2248 (2) Å	0.58 × 0.35 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	1954 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1551 reflections with I > 2σ(I)
T_min = 0.809, T_max = 0.945	R_int = 0.040
33450 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.211	H-atom parameters constrained
S = 1.20	Δρ_max = 0.32 e Å⁻³
1954 reflections	Δρ_min = −0.42 e Å⁻³
106 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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···O1^xiv	3.232 (4)
Cl1···H15ⁱⁱⁱ	2.8200	C2···O1^x	3.232 (4)
S1···O4^iv	3.494 (4)	C3···O1^xiv	3.412 (4)
S1···O4^v	3.276 (4)	C3···O1^x	3.412 (4)
S1···C4^iv	3.605 (4)	C4···S1^xii	3.605 (4)
S1···O4^vi	3.494 (4)	C4···O1^xiv	2.970 (5)
S1···O4^vii	3.276 (4)	C4···S1^xv	3.605 (4)
S1···C4^vi	3.605 (4)	C4···O1^x	2.970 (5)
O1···O4^viii	3.152 (5)	C12···C15^xiv	3.511 (9)
O1···C2^viii	3.232 (4)	C15···C12^viii	3.511 (9)
O1···C3^viii	3.412 (4)	C15···Cl1ⁱⁱⁱ	3.645 (9)
O1···C4^viii	2.970 (5)	C16···O1	3.322 (5)
O1···C16	3.322 (5)	C3···H16	2.7700
O1···C2^ix	3.232 (4)	C16···H3B	2.7500
O1···C3^ix	3.412 (4)	H2···O1^xiv	2.4300
O1···O4^ix	3.152 (5)	H2···H12	2.3300
O1···C16ⁱ	3.322 (5)	H2···O4^v	2.7900
O1···C4^ix	2.970 (5)	H2···O4^vii	2.7900
O4···O1^x	3.152 (5)	H2···O1^x	2.4300
O4···S1^xi	3.276 (4)	H2···H2ⁱ	2.5000
O4···S1^xii	3.494 (4)	H3A···H12^xi	2.5900
O4···S1^xiii	3.276 (4)	H3B···O1	2.6500
O4···O1^xiv	3.152 (5)	H3B···C16	2.7500
O4···S1^xv	3.494 (4)	H3B···H16	2.2300
O1···H3Bⁱ	2.6500	H12···H2	2.3300
O1···H2^viii	2.4300	H12···H3A^vii	2.5900
O1···H2^ix	2.4300	H15···Cl1ⁱⁱ	2.8200
O1···H3B	2.6500	H16···C3	2.7700
O4···H2^xiii	2.7900	H16···H3B	2.2300
O4···H2^xi	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)

Symmetry codes: (i) x, −y+1/2, z; (ii) −x+1/2, −y, z−1/2; (iii) −x+1/2, −y, z+1/2; (iv) x−1/2, −y+1/2, −z+1/2; (v) x−1/2, −y+1/2, −z+3/2; (vi) x−1/2, y, −z+1/2; (vii) x−1/2, y, −z+3/2; (viii) x, y, z−1; (ix) x, −y+1/2, z−1; (x) x, −y+1/2, z+1; (xi) x+1/2, y, −z+3/2; (xii) x+1/2, −y+1/2, −z+1/2; (xiii) x+1/2, −y+1/2, −z+3/2; (xiv) x, y, z+1; (xv) x+1/2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1^xiv	0.98	2.43	3.232 (4)	138
C15—H15···Cl1ⁱⁱ	0.93	2.82	3.745 (9)	170

Symmetry codes: (ii) −x+1/2, −y, z−1/2; (xiv) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅ClO₂S
M_r	318.81
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	296
a, b, c (Å)	11.5195 (5), 25.7589 (12), 5.2248 (2)
V (Å³)	1550.35 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.58 × 0.35 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.809, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	33450, 1954, 1551
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.211, 1.20
No. of reflections	1954
No. of parameters	106
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.42

Computer programs: APEX2 (Bruker, 2004), SAINT-NT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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) x, y, z+1; (ii) −x+1/2, −y, z−1/2.

Acknowledgements

AT thanks the UGC, India, for the award of a Minor Research Project [File No. MRP-2355/06(UGC-SERO), Link No. 2355, 10/01/2007]. RJB acknowledges the NSF–MRI program for funding to purchase the X-ray CCD diffractometer.

References

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-r-(4-Chloro­phen­yl)-6-c-phenyl-3,4,5,6-tetra­hydro-2H-thio­pyran-4-one 1-oxide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-r-(4-Chlorophenyl)-6-c-phenyl-3,4,5,6-tetrahydro-2H-thiopyran-4-one 1-oxide