The supramolecular structure of 6-hydroxy-1,3-benzoxa­thiol-2-one (tioxolone)

Byres, M.; Cox, P.J.

doi:10.1107/S0108270104008236

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 60| Part 6| June 2004| Pages o395-o396

doi:10.1107/S0108270104008236

The supramolecular structure of 6-hydroxy-1,3-benzoxathiol-2-one (tioxolone)

Maureen Byres ^a and Philip J. Cox ^a ^*

^aSchool of Pharmacy, The Robert Gordon University, Schoolhill, Aberdeen AB10 1FR, Scotland
^*Correspondence e-mail: p.j.cox@rgu.ac.uk

(Received 10 March 2004; accepted 5 April 2004; online 11 May 2004)

The planar molecules of 6-hydroxy-1,3-benzoxathiol-2-one, C₇H₄O₃S, are linked by extensive O—H⋯O and C—H⋯O hydrogen bonding and are further stablilized by face-to-face π–π interactions.

Comment

The title compound, (I), also known as tioxolone, has been used in the treatment of acne due to its sulfur content (Lius & Sennerfeldt, 1979 ). It is reported to possess cytostatic (Goeth & Wildfeuer, 1969 ), antipsoriatic, antibacterial and antimycotic properties (Wildfeuer, 1970 ). It is also added to some cosmetics (e.g. hair shampoos and skin cleansers), due to claims for its oil-regulating and antibacterial properties.

The bond lengths and angles in (I) are as expected (Table 1) for this almost planar molecule, where the greatest torsion angle deviation from zero or ±180° is seen for C2—O1—C7—O2 [−177.49 (18)°]. For simple molecules of this kind, with a hydrogen-bond donor group (—OH) at one end and an acceptor (C=O) at the other, it can be predicted that a continuous chain of hydrogen-bonded molecules will be present in the crystal lattice. Such is the case for 5-hydroxybenzofuran-(3H)-one (Bocelli & Grenier-Loustalot, 1982 ). For (I), this is indeed the case, and details of the classical O3—H3⋯O2ⁱ hydrogen bond are given in Table 2 [symmetry code: (i) 1 + x, $[{1 \over 2}]$ − y, z − $[{1 \over 2}]$ ].

Further examination of non-bonded contacts also reveals two intermolecular C—H⋯O bonds (Table 2). Hence, as shown in Fig. 2, each molecule of (I) is linked through six hydrogen bonds to five adjacent molecules. One C—H⋯O bond is arranged as described by graph set R₂²(8) about inversion centres, as shown in Fig. 3. The other C—H⋯O bond links the O2 keto group to C4; hence atom O2 acts as an acceptor for two H atoms, with an H3⋯O2⋯H4 angle of 120°. The resultant C—H⋯O hydrogen-bonding motif may be described as zigzag ribbons. Hydroxy atom O3 acts as both a donor, in forming the continuous chain of classical hydrogen bonds in the [20 $[\overline 1]$ ] direction, and an acceptor, in the formation of the R₂²(8) rings. Only one H atom in the molecule, namely H5, is not involved in hydrogen bonding.

The three-dimensional framework of (I) is further stabilized by π–π interactions (Steed & Atwood, 2000 ) between the oxathiolone and benzene rings in partially overlapping molecules (Fig. 4). Here, the interplanar spacing is 3.377 (3) Å, the distance between the centroids of the two rings is 3.508 (2) Å, the two centres are offset by 0.961 (2) Å and the interacting molecules are related by unit-cell translations along the short a axis.

A search of the Cambridge Structural Database (Version 5.25, January 2004 update; Allen, 2002 ) shows that the ring system in (I) is unique among crystal structures examined to date. Similar, but not identical, ring systems which lack classical hydrogen bonding are present in the crystal structures of 5,7-di-tert-butyl-3H-2,1-benzoxathiol-3-one (Krische et al., 1982 ) and 3-oxo-3H-2,1-benzoxathiole-7-carboxylic acid methyl ester (Walter et al., 1978 ).

Figure 1
A view of the atomic arrangement in (I

), showing the atom-numbering scheme and 50% probability displacement ellipsoids.

Figure 2
A partial packing diagram for (I

), showing the intermolecular hydrogen bonding [symmetry codes: (i) 1 + x, $[{1 \over 2}]$ − y, z − $[{1 \over 2}]$ ; (ii) 1 − x, 1 − y, 1 − z; (iii) 1 −x, y − $[{1 \over 2}]$ , $[{3 \over 2}]$ − z; (iv) x − 1, $[{1 \over 2}]$ − y, z + $[{1 \over 2}]$ ; (v) 1 − x, y + $[{1 \over 2}]$ , $[{3 \over 2}]$ − z].

Figure 3
The C—H⋯O hydrogen bonding in the crystal structure of (I

Figure 4
A partial packing diagram for (I

), showing molecules stacked along the a axis. Ring centroids (Cg1 for the oxathiolone ring and Cg2 for the benzene ring) involved in the π–π interactions are joined by dashed lines.

Experimental

The title compound was purchased from Sigma and recrystallized from n-butanol. Data were collected on a very small crystal (2 × 10⁻⁵ mm³).

Crystal data

C₇H₄O₃S
M_r = 168.16
Monoclinic, P2₁/c
a = 3.7620 (2) Å
b = 10.686 (4) Å
c = 16.447 (9) Å
β = 91.424 (16)°
V = 661.0 (4) Å³
Z = 4
D_x = 1.69 Mg m⁻³
Mo Kα radiation
Cell parameters from 18 478 reflections
θ = 2.9–27.5°
μ = 0.43 mm⁻¹
T = 120 (2) K
Needle, colourless
0.10 × 0.02 × 0.01 mm

Data collection

Enraf–Nonius KappaCCD area-detector diffractometer
φ and ω scans to fill Ewald sphere
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.965, T_max = 1.000
11 482 measured reflections
1502 independent reflections
1174 reflections with I > 2σ(I)
R_int = 0.08
θ_max = 27.5°
h = −4 → 4
k = −13 → 13
l = −21 → 21

Refinement

Refinement on F²
R(F) = 0.037
wR(F²) = 0.083
S = 1.05
1502 reflections
103 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F_o²) + (0.0338P)² + 0.3671P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

S1—C7	1.747 (2)
S1—C3	1.748 (2)
O1—C7	1.362 (2)
O2—C7	1.207 (2)

C7—S1—C3	90.11 (9)
C7—O1—C2	112.08 (15)
C2—C3—S1	110.61 (14)
O2—C7—S1	127.03 (16)
O1—C7—S1	112.63 (13)

C2—O1—C7—O2	−177.49 (18)
C2—O1—C7—S1	2.3 (2)

Table 2
Hydrogen-bonding geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.86 (2)	1.91 (2)	2.767 (2)	172 (2)
C1—H1⋯O3ⁱⁱ	0.95	2.42	3.365 (3)	174
C4—H4⋯O2ⁱⁱⁱ	0.95	2.53	3.437 (3)	161
Symmetry codes: (i) $[1+x,{\script{1\over 2}}-y,z-{\script{1\over 2}}]$ ; (ii) 1-x,1-y,1-z; (iii) $[1-x,y-{\script{1\over 2}},{\script{3\over 2}}-z]$ .

Due to the small amount of scattering material, it was necessary to stabilize the position of the hydroxy H atom using distance restraints [O3—H3 = 0.90 (2) Å and H3⋯O2 = 1.90 (2) Å] that led to acceptable geometries. The remaining H atoms were allowed to ride on their attached atoms, with C—H distances constrained to 0.95 Å. For all H atoms, U_iso(H) = 1.2U_eq(parent atom).

Data collection: DENZO (Otwinowski & Minor, 1997 ) and COLLECT (Nonius, 1998 ); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S0108270104008236/bm1566sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270104008236/bm1566Isup2.hkl

Comment top

The title compound, (I), also known as tioxolone, has been used in the treatment of acne due to its sulfur content (Lius & Sennerfeldt, 1979). It is reported to possess cytostatic (Goeth & Wildfeuer, 1969), antipsoriatic, antibacterial and antimycotic properties (Wildfeuer, 1970). It is also added to some cosmetics (e.g. hair shampoos and skin cleansers), due to claims for its oil-regulating and antibacterial properties. \sch

The bond lengths and angles in (I) are as expected (Table 1) for this almost planar molecule, where the greatest torsion angle deviation from zero or ±180° is seen for C2—O1—C7—O2 [−177.49 (18)°]. For simple molecules of this kind, with a hydrogen-bond donor group (–OH) at one end and an acceptor (C═O) at the other, it can be predicted that a continuous chain of hydrogen-bonded molecules will be present in the crystal lattice. Such is the case for 5-hydroxy-2(3H)-benzofuranone (Bocelli & Grenier-Loustalot, 1982). For (I), this is indeed the case, and details of the classical O3—H3···O2ⁱ hydrogen bond are given in Table 2 [symmetry code: (i) 1 + x, 1/2 − y, z − 1/2].

Further examination of non-bonded contacts also reveals two intermolecular C—H···O bonds (Table 2). Hence, as shown in Fig. 2, each molecule of (I) is linked through six hydrogen bonds to five adjacent molecules. One C—H···O bond is arranged as described by graph set R₂²(8) about inversion centres, as shown in Fig.3. The other C—H···O bond links the O2 keto group to C4, hence atom O2 acts as an acceptor for two H atoms, with H3···O2···H4 120°. The resultant C—H···O hydrogen-bonding motif may be described as zigzag ribbons. The hydroxy atom O3 acts as both a donor, in forming the continuous chain of classical hydrogen bonds in the [201] direction, and as an acceptor, in the formation of the R₂²(8) rings. Only one H atom in the molecule, namely H5, is not involved in hydrogen bonding.

The three-dimensional framework of (I) is further stabilized by π–π interactions (Steed & Atwood, 2000) between the oxathiolone and phenyl rings in partially overlapping molecules (Fig. 4). Here, the interplanar spacing is 3.377 (3) Å, the distance between the centres of gravity of the two rings is 3.508 (2) Å, the two centres are offset by 0.961 (2) Å and the interacting molecules are related by unit-cell translations along the short a axis.

A search of the Cambridge Structural Database (Version?; Allen, 2002) shows that the ring system in (I) is unique among crystal structures examined to date. Similar, but not identical, ring systems which lack classical hydrogen bonding are present in the crystal structures of 5,7-di-tert-butyl-3H-2,1-benzoxathiol-3-one (Krische et al., 1982) and 3-oxo-3H-2,1-benzoxathiole-7-carboxylic acid methyl ester (Walter et al., 1978).

Experimental top

The title compound was purchased from Sigma and recrystallized from n-butanol. Data were collected on a very small crystal (2 × 10⁻⁵mm³).

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A view of the atomic arrangement in (I), showing the atom-numbering scheme and with 50% probability displacement ellipsoids.
	Fig. 2. A partial packing diagram for (I), showing the intermolecular hydrogen bonding [symmetry codes: (i) 1 + x, 1/2 − y, z − 1/2; (ii) 1 − x, 1 − y, 1 − z; (iii) 1 − x, y − 1/2, 3/2 − z; (iv) x − 1, 1/2 − y, z + 1/2; (v) 1 − x, y + 1/2, 3/2 − z].
	Fig. 3. The C—H···O hydrogen bonding in the crystal of (I).
	Fig. 4. A partial packing diagram for (I), showing molecules stacked along the a axis. Ring centroids (Cg1 for the oxathiolone ring and Cg2 for the phenyl ring) involved in the π–π interactions are joined by dotted lines.

(I) top

Crystal data top

C₇H₄O₃S	F(000) = 344
M_r = 168.16	D_x = 1.69 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 18478 reflections
a = 3.7620 (2) Å	θ = 2.9–27.5°
b = 10.686 (4) Å	µ = 0.43 mm⁻¹
c = 16.447 (9) Å	T = 120 K
β = 91.424 (16)°	Needle, colourless
V = 661.0 (4) Å³	0.1 × 0.02 × 0.01 mm
Z = 4

Data collection top

Enraf Nonius KappaCCD area-detector diffractometer	1174 reflections with I > 2σ(I)
ϕ and ω scans to fill Ewald sphere	R_int = 0.08
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	θ_max = 27.5°, θ_min = 3.1°
T_min = 0.965, T_max = 1.000	h = −4→4
11482 measured reflections	k = −13→13
1502 independent reflections	l = −21→21

Refinement top

Refinement on F²	2 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0338P)² + 0.3671P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.083	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.33 e Å⁻³
1502 reflections	Δρ_min = −0.30 e Å⁻³
103 parameters

Crystal data top

C₇H₄O₃S	V = 661.0 (4) Å³
M_r = 168.16	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 3.7620 (2) Å	µ = 0.43 mm⁻¹
b = 10.686 (4) Å	T = 120 K
c = 16.447 (9) Å	0.1 × 0.02 × 0.01 mm
β = 91.424 (16)°

Data collection top

Enraf Nonius KappaCCD area-detector diffractometer	1502 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	1174 reflections with I > 2σ(I)
T_min = 0.965, T_max = 1.000	R_int = 0.08
11482 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	2 restraints
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.33 e Å⁻³
1502 reflections	Δρ_min = −0.30 e Å⁻³
103 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1	0.31869 (13)	0.12103 (4)	0.76562 (3)	0.01635 (16)
O1	0.2310 (4)	0.35210 (12)	0.72071 (8)	0.0161 (3)
O2	0.0223 (4)	0.31042 (13)	0.84351 (8)	0.0215 (4)
O3	0.6947 (4)	0.34264 (13)	0.45481 (8)	0.0211 (4)
H3	0.802 (6)	0.2907 (19)	0.4239 (12)	0.025*
C1	0.4639 (5)	0.35334 (18)	0.58528 (11)	0.0151 (4)
H1	0.4152	0.4399	0.5781	0.018*
C2	0.3875 (5)	0.29119 (17)	0.65601 (11)	0.0135 (4)
C3	0.4551 (5)	0.16607 (18)	0.66909 (11)	0.0137 (4)
C4	0.6082 (5)	0.09592 (18)	0.60835 (11)	0.0156 (4)
H4	0.6574	0.0095	0.6161	0.019*
C5	0.6879 (5)	0.15485 (18)	0.53593 (11)	0.0151 (4)
H5	0.7918	0.1082	0.4935	0.018*
C6	0.6171 (5)	0.28151 (18)	0.52483 (11)	0.0152 (4)
C7	0.1683 (5)	0.27299 (18)	0.78366 (11)	0.0157 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0207 (3)	0.0143 (3)	0.0141 (2)	−0.0007 (2)	0.00184 (18)	0.0018 (2)
O1	0.0218 (8)	0.0138 (7)	0.0129 (7)	0.0011 (5)	0.0037 (5)	0.0001 (5)
O2	0.0278 (9)	0.0192 (8)	0.0178 (7)	−0.0048 (6)	0.0093 (6)	−0.0035 (6)
O3	0.0330 (9)	0.0181 (8)	0.0125 (7)	0.0052 (6)	0.0082 (6)	0.0022 (6)
C1	0.0178 (10)	0.0123 (10)	0.0154 (9)	0.0002 (8)	0.0000 (8)	0.0002 (7)
C2	0.0142 (10)	0.0136 (10)	0.0129 (9)	−0.0005 (8)	0.0004 (7)	−0.0040 (7)
C3	0.0141 (10)	0.0144 (10)	0.0124 (9)	−0.0016 (7)	−0.0019 (8)	0.0030 (7)
C4	0.0160 (10)	0.0121 (10)	0.0186 (10)	0.0035 (8)	−0.0025 (8)	0.0005 (8)
C5	0.0153 (10)	0.0164 (10)	0.0135 (9)	0.0011 (8)	−0.0001 (8)	−0.0034 (7)
C6	0.0164 (11)	0.0173 (10)	0.0119 (9)	0.0001 (8)	−0.0009 (8)	0.0012 (8)
C7	0.0165 (10)	0.0161 (10)	0.0144 (9)	−0.0038 (8)	0.0005 (8)	−0.0003 (8)

Geometric parameters (Å, º) top

S1—C7	1.747 (2)	C1—C6	1.392 (3)
S1—C3	1.748 (2)	C1—H1	0.95
O1—C7	1.362 (2)	C2—C3	1.377 (3)
O1—C2	1.391 (2)	C3—C4	1.386 (3)
O2—C7	1.207 (2)	C4—C5	1.387 (3)
O3—C6	1.362 (2)	C4—H4	0.95
O3—H3	0.860 (15)	C5—C6	1.391 (3)
C1—C2	1.376 (3)	C5—H5	0.95

C7—S1—C3	90.11 (9)	C3—C4—C5	118.44 (18)
C7—O1—C2	112.08 (15)	C3—C4—H4	120.8
C6—O3—H3	107.7 (15)	C5—C4—H4	120.8
C2—C1—C6	115.89 (18)	C4—C5—C6	120.66 (18)
C2—C1—H1	122.1	C4—C5—H5	119.7
C6—C1—H1	122.1	C6—C5—H5	119.7
C1—C2—C3	123.99 (17)	O3—C6—C5	122.24 (17)
C1—C2—O1	121.49 (17)	O3—C6—C1	116.15 (17)
C3—C2—O1	114.52 (16)	C5—C6—C1	121.62 (18)
C2—C3—C4	119.41 (17)	O2—C7—O1	120.34 (18)
C2—C3—S1	110.61 (14)	O2—C7—S1	127.03 (16)
C4—C3—S1	129.97 (15)	O1—C7—S1	112.63 (13)

C6—C1—C2—C3	0.3 (3)	S1—C3—C4—C5	179.12 (15)
C6—C1—C2—O1	−179.38 (17)	C3—C4—C5—C6	0.3 (3)
C7—O1—C2—C1	178.14 (17)	C4—C5—C6—O3	179.41 (18)
C7—O1—C2—C3	−1.6 (2)	C4—C5—C6—C1	−0.2 (3)
C1—C2—C3—C4	−0.2 (3)	C2—C1—C6—O3	−179.74 (17)
O1—C2—C3—C4	179.49 (17)	C2—C1—C6—C5	−0.1 (3)
C1—C2—C3—S1	−179.59 (16)	C2—O1—C7—O2	−177.49 (18)
O1—C2—C3—S1	0.1 (2)	C2—O1—C7—S1	2.3 (2)
C7—S1—C3—C2	0.98 (15)	C3—S1—C7—O2	177.9 (2)
C7—S1—C3—C4	−178.3 (2)	C3—S1—C7—O1	−1.90 (15)
C2—C3—C4—C5	−0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.86 (2)	1.91 (2)	2.767 (2)	172 (2)
C1—H1···O3ⁱⁱ	0.95	2.42	3.365 (3)	174
C4—H4···O2ⁱⁱⁱ	0.95	2.53	3.437 (3)	161

Symmetry codes: (i) x+1, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₇H₄O₃S
M_r	168.16
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	3.7620 (2), 10.686 (4), 16.447 (9)
β (°)	91.424 (16)
V (Å³)	661.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.1 × 0.02 × 0.01

Data collection
Diffractometer	Enraf Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.965, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11482, 1502, 1174
R_int	0.08
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.083, 1.05
No. of reflections	1502
No. of parameters	103
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.30

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998), DENZO and COLLECT, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

S1—C7	1.747 (2)	O1—C7	1.362 (2)
S1—C3	1.748 (2)	O2—C7	1.207 (2)

C7—S1—C3	90.11 (9)	O2—C7—S1	127.03 (16)
C7—O1—C2	112.08 (15)	O1—C7—S1	112.63 (13)
C2—C3—S1	110.61 (14)

C2—O1—C7—O2	−177.49 (18)	C2—O1—C7—S1	2.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.860 (15)	1.912 (15)	2.767 (2)	172 (2)
C1—H1···O3ⁱⁱ	0.95	2.42	3.365 (3)	174
C4—H4···O2ⁱⁱⁱ	0.95	2.53	3.437 (3)	161

Symmetry codes: (i) x+1, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y−1/2, −z+3/2.

Acknowledgements

The authors thank the EPSRC National X-ray Crystallography Service at Southampton University for collecting the data.

References

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ISSN: 2053-2296

Volume 60| Part 6| June 2004| Pages o395-o396

doi:10.1107/S0108270104008236

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

The supramolecular structure of 6-hy­droxy-1,3-benzoxa­thiol-2-one (tioxolone)

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

The supramolecular structure of 6-hydroxy-1,3-benzoxathiol-2-one (tioxolone)