2-(4-Methyl­phenyl­sulfonamido)acetic acid

He, D.-F.; Ma, X.-J.; Ma, L.L.; Shu, S.; Jin, Z.-M.

doi:10.1107/S1600536807037749

2-(4-Methylphenylsulfonamido)acetic acid

D.-F. He, X.-J. Ma, L. L. Ma, S. Shu and Z.-M. Jin

In the title compound, C₉H₁₁O₄NS, there are two crystallographically independent molecules in the asymmetric unit. The S atoms are in a distorted tetrahedral configuration. Symmetry-related molecules are linked to form dimers via O—H

O hydrogen bonding, and the dimers are associated to form infinite chains via N—H

O hydrogen bonding. There are close C—H

O approaches of 3.342 (7) and 3.353 (7) Å between the two independent molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037749/fl2149sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037749/fl2149Isup2.hkl Contains datablock I

CCDC reference: 660219

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Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.010 Å
R factor = 0.056
wR factor = 0.113
Data-to-parameter ratio = 12.8

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Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10

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   0 ALERT level B = Potentially serious problem
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   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
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Comment top

The sulfonamide group is present in many bioactive compounds (Yan et al., 2007; Patani & Lavoie, 1996) and may be used as a protecting group (Yin et al., 2007). Many sulfonamide derivatives have been synthesized, such as sulfacetamide, sulfapyridine, sulfaguanidine, sulfathiazole, etc. We report here the synthesis and crystal structure of the title compound, (I).

As shown in Fig. 1, there are two crystallographically independent molecules in the asymmetric unit. Most bond lengths and angles in (I) are within normal ranges with the geometries around S atom being distorted tetrahedra (Lehman et al., 1981; Starilkova et al., 1982), with two O atoms, one N and C atom.

The self-related independent molecules of (I) are linked via O—H···O hydrogen bonds to form dimers (Fig. 2 and Table 2), which are frequently observed in carboxlic acid that can be described by a graph set of R₂²(8) (Bernstein et al., 1995; Etter, 1990). Such dimers are associated via N—H···O hydrogen bonds to form infinite chains. In the crystal, the independent molecules are linked with each other by the C1—H1B···O5^v and C10—H10B···O2^vi hydrogen bonds.

Related literature top

For the biological activity of sulfonamides, see: Yan et al. (2007); Patani & Lavoie (1996). For the chemistry of sulfonamides, see: Yin et al. (2007). For geometry, see: Lehman et al. (1981); Starilkova et al. (1982); Bernstein et al. (1995); Etter (1990).

Experimental top

4-Methylbenzene-1-sulfonyl chloride (0.02 mol, 3.81 g) and 2-aminoacetic acid (0.02 mol,1.50 g) were added together at room temperature with stirring. The reaction was allowed to proceed for 8 h at room temperature. The purified product was dissovled in acetone, approximately 10 days later single crystals of (I) were formed.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The asymmetric cell unit of (I) with atom labels, showing 30% probability displacement ellipsoids. The hydrogen bond linking the two unique molecules is shown as a dashed line.
	Fig. 2. The crystal packing of (I) viewed down along the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonds are ommitted for clarity.

2-(4-Methylphenylsulfonamido)acetic acid top

Crystal data top

C₉H₁₁NO₄S	F(000) = 960
M_r = 229.26	D_x = 1.523 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1978 reflections
a = 22.3240 (19) Å	θ = 2.6–24.3°
b = 5.7263 (5) Å	µ = 0.32 mm⁻¹
c = 16.5526 (14) Å	T = 298 K
β = 109.069 (2)°	Rod, colourless
V = 1999.9 (3) Å³	0.27 × 0.13 × 0.11 mm
Z = 8

Data collection top

Bruker APEX area-detector diffractometer	3524 independent reflections
Radiation source: fine-focus sealed tube	2969 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
φ and ω scans	θ_max = 25.0°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −24→26
T_min = 0.919, T_max = 0.956	k = −6→6
9980 measured reflections	l = −18→19

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.29	w = 1/[σ²(F_o²) + (0.0579P)² + 6.265P] where P = (F_o² + 2F_c²)/3
3524 reflections	(Δ/σ)_max = 0.001
275 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₉H₁₁NO₄S	V = 1999.9 (3) Å³
M_r = 229.26	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 22.3240 (19) Å	µ = 0.32 mm⁻¹
b = 5.7263 (5) Å	T = 298 K
c = 16.5526 (14) Å	0.27 × 0.13 × 0.11 mm
β = 109.069 (2)°

Data collection top

Bruker APEX area-detector diffractometer	3524 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2969 reflections with I > 2σ(I)
T_min = 0.919, T_max = 0.956	R_int = 0.049
9980 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.29	Δρ_max = 0.62 e Å⁻³
3524 reflections	Δρ_min = −0.41 e Å⁻³
275 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.

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.

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

	x	y	z	U_iso*/U_eq
S1	0.39781 (7)	0.4002 (3)	0.17822 (9)	0.0304 (4)
S2	0.10566 (7)	0.3305 (3)	0.28814 (10)	0.0337 (4)
O1	0.4177 (2)	0.4520 (8)	0.1064 (3)	0.0430 (12)
O2	0.3857 (2)	0.5823 (8)	0.2284 (3)	0.0448 (12)
O3	0.4516 (2)	0.2409 (9)	0.4589 (3)	0.0496 (13)
H3	0.4681	0.3220	0.5012	0.074*
O4	0.5043 (2)	0.4794 (8)	0.3988 (2)	0.0378 (11)
O5	0.1138 (2)	0.5130 (8)	0.3486 (3)	0.0471 (12)
O6	0.0937 (2)	0.3832 (9)	0.2000 (3)	0.0499 (13)
O7	0.0451 (2)	0.2317 (9)	0.5077 (3)	0.0534 (13)
H7	0.0287	0.3211	0.5331	0.080*
O8	−0.0094 (2)	0.4433 (9)	0.3949 (3)	0.0463 (12)
N1	0.4533 (2)	0.2403 (9)	0.2423 (3)	0.0324 (12)
H1	0.4873	0.2066	0.2310	0.039*
N2	0.0455 (2)	0.1782 (10)	0.2924 (3)	0.0374 (13)
H2	0.0144	0.1465	0.2470	0.045*
C1	0.1630 (3)	−0.1992 (14)	0.0510 (5)	0.056 (2)
H1A	0.1703	−0.3438	0.0821	0.083*
H1B	0.1541	−0.2304	−0.0087	0.083*
H1C	0.1276	−0.1201	0.0594	0.083*
C2	0.2204 (3)	−0.0497 (11)	0.0825 (4)	0.0383 (16)
C3	0.2776 (3)	−0.1197 (11)	0.0739 (4)	0.0374 (16)
H3A	0.2796	−0.2623	0.0481	0.045*
C4	0.3313 (3)	0.0154 (11)	0.1025 (4)	0.0364 (15)
H4	0.3688	−0.0330	0.0946	0.044*
C5	0.3288 (3)	0.2253 (11)	0.1432 (4)	0.0317 (14)
C6	0.2732 (3)	0.2982 (12)	0.1535 (4)	0.0421 (17)
H6	0.2716	0.4380	0.1813	0.050*
C7	0.2202 (3)	0.1619 (13)	0.1223 (4)	0.0447 (18)
H7A	0.1824	0.2144	0.1281	0.054*
C8	0.4430 (3)	0.1568 (11)	0.3196 (4)	0.0329 (14)
H8A	0.4616	0.0026	0.3330	0.039*
H8B	0.3978	0.1414	0.3087	0.039*
C9	0.4702 (3)	0.3116 (11)	0.3958 (4)	0.0302 (14)
C10	0.3427 (3)	−0.2626 (13)	0.3970 (4)	0.0487 (18)
H10A	0.3753	−0.1830	0.4409	0.073*
H10B	0.3564	−0.2870	0.3484	0.073*
H10C	0.3343	−0.4107	0.4182	0.073*
C11	0.2833 (3)	−0.1171 (12)	0.3709 (4)	0.0377 (16)
C12	0.2297 (3)	−0.1886 (12)	0.3062 (4)	0.0417 (16)
H12	0.2306	−0.3289	0.2784	0.050*
C13	0.1752 (3)	−0.0585 (11)	0.2820 (4)	0.0390 (16)
H13	0.1396	−0.1101	0.2383	0.047*
C14	0.1737 (3)	0.1500 (11)	0.3231 (4)	0.0324 (14)
C15	0.2263 (3)	0.2262 (12)	0.3882 (4)	0.0414 (17)
H15	0.2253	0.3654	0.4167	0.050*
C16	0.2804 (3)	0.0919 (12)	0.4102 (4)	0.0419 (16)
H16	0.3163	0.1446	0.4531	0.050*
C17	0.0465 (3)	0.0973 (12)	0.3763 (4)	0.0406 (16)
H17A	0.0894	0.0511	0.4090	0.049*
H17B	0.0197	−0.0396	0.3691	0.049*
C18	0.0242 (3)	0.2790 (12)	0.4257 (4)	0.0346 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0359 (9)	0.0317 (9)	0.0215 (8)	0.0010 (7)	0.0065 (6)	−0.0006 (6)
S2	0.0331 (9)	0.0361 (9)	0.0313 (9)	0.0002 (7)	0.0096 (7)	0.0007 (7)
O1	0.049 (3)	0.050 (3)	0.028 (2)	−0.008 (2)	0.010 (2)	0.011 (2)
O2	0.053 (3)	0.040 (3)	0.038 (3)	0.002 (2)	0.010 (2)	−0.006 (2)
O3	0.068 (3)	0.061 (3)	0.024 (2)	−0.018 (3)	0.021 (2)	0.000 (2)
O4	0.042 (3)	0.049 (3)	0.023 (2)	−0.015 (2)	0.0099 (19)	−0.005 (2)
O5	0.044 (3)	0.045 (3)	0.054 (3)	0.000 (2)	0.017 (2)	−0.009 (2)
O6	0.048 (3)	0.060 (3)	0.043 (3)	0.009 (2)	0.017 (2)	0.012 (2)
O7	0.068 (4)	0.060 (3)	0.032 (3)	0.006 (3)	0.016 (2)	0.005 (2)
O8	0.044 (3)	0.057 (3)	0.036 (3)	0.015 (3)	0.012 (2)	0.005 (2)
N1	0.027 (3)	0.043 (3)	0.030 (3)	0.001 (2)	0.013 (2)	0.000 (2)
N2	0.029 (3)	0.050 (3)	0.028 (3)	−0.002 (3)	0.003 (2)	−0.004 (2)
C1	0.051 (5)	0.060 (5)	0.047 (4)	−0.004 (4)	0.005 (4)	0.010 (4)
C2	0.040 (4)	0.035 (4)	0.035 (4)	−0.004 (3)	0.005 (3)	0.011 (3)
C3	0.042 (4)	0.029 (3)	0.034 (4)	0.004 (3)	0.002 (3)	−0.003 (3)
C4	0.030 (3)	0.044 (4)	0.033 (4)	0.005 (3)	0.007 (3)	0.001 (3)
C5	0.038 (4)	0.035 (4)	0.022 (3)	0.003 (3)	0.008 (3)	0.004 (3)
C6	0.041 (4)	0.040 (4)	0.050 (4)	0.004 (3)	0.021 (3)	−0.003 (3)
C7	0.038 (4)	0.050 (4)	0.051 (4)	0.008 (3)	0.020 (3)	0.014 (4)
C8	0.039 (4)	0.031 (3)	0.027 (3)	0.002 (3)	0.009 (3)	0.002 (3)
C9	0.025 (3)	0.042 (4)	0.020 (3)	0.007 (3)	0.004 (2)	0.004 (3)
C10	0.053 (5)	0.049 (4)	0.050 (4)	0.004 (4)	0.025 (4)	0.008 (4)
C11	0.042 (4)	0.040 (4)	0.037 (4)	0.004 (3)	0.020 (3)	0.012 (3)
C12	0.049 (4)	0.038 (4)	0.037 (4)	0.006 (3)	0.014 (3)	−0.006 (3)
C13	0.041 (4)	0.040 (4)	0.033 (4)	−0.010 (3)	0.009 (3)	−0.009 (3)
C14	0.032 (3)	0.034 (4)	0.032 (3)	−0.004 (3)	0.012 (3)	0.002 (3)
C15	0.049 (4)	0.043 (4)	0.029 (4)	−0.001 (3)	0.009 (3)	−0.010 (3)
C16	0.041 (4)	0.045 (4)	0.035 (4)	−0.004 (3)	0.004 (3)	−0.004 (3)
C17	0.037 (4)	0.041 (4)	0.041 (4)	−0.007 (3)	0.009 (3)	0.002 (3)
C18	0.030 (4)	0.043 (4)	0.030 (4)	−0.011 (3)	0.009 (3)	−0.002 (3)

Geometric parameters (Å, º) top

S1—O2	1.413 (4)	C4—C5	1.388 (9)
S1—O1	1.429 (4)	C4—H4	0.9300
S1—N1	1.625 (5)	C5—C6	1.370 (8)
S1—C5	1.769 (6)	C6—C7	1.371 (9)
S2—O5	1.417 (5)	C6—H6	0.9300
S2—O6	1.427 (5)	C7—H7A	0.9300
S2—N2	1.622 (5)	C8—C9	1.499 (8)
S2—C14	1.771 (6)	C8—H8A	0.9700
O3—C9	1.308 (7)	C8—H8B	0.9700
O3—H3	0.8200	C10—C11	1.506 (9)
O4—C9	1.216 (7)	C10—H10A	0.9600
O7—C18	1.311 (7)	C10—H10B	0.9600
O7—H7	0.8200	C10—H10C	0.9600
O8—C18	1.208 (8)	C11—C16	1.373 (9)
N1—C8	1.453 (7)	C11—C12	1.382 (9)
N1—H1	0.8600	C12—C13	1.370 (9)
N2—C17	1.457 (8)	C12—H12	0.9300
N2—H2	0.8600	C13—C14	1.381 (9)
C1—C2	1.486 (9)	C13—H13	0.9300
C1—H1A	0.9600	C14—C15	1.380 (8)
C1—H1B	0.9600	C15—C16	1.377 (9)
C1—H1C	0.9600	C15—H15	0.9300
C2—C7	1.380 (10)	C16—H16	0.9300
C2—C3	1.389 (9)	C17—C18	1.506 (9)
C3—C4	1.374 (9)	C17—H17A	0.9700
C3—H3A	0.9300	C17—H17B	0.9700

O2—S1—O1	120.4 (3)	C2—C7—H7A	118.6
O2—S1—N1	106.4 (3)	N1—C8—C9	114.2 (5)
O1—S1—N1	106.4 (3)	N1—C8—H8A	108.7
O2—S1—C5	107.3 (3)	C9—C8—H8A	108.7
O1—S1—C5	108.6 (3)	N1—C8—H8B	108.7
N1—S1—C5	107.0 (3)	C9—C8—H8B	108.7
O5—S2—O6	120.3 (3)	H8A—C8—H8B	107.6
O5—S2—N2	106.4 (3)	O4—C9—O3	124.7 (6)
O6—S2—N2	106.1 (3)	O4—C9—C8	125.2 (5)
O5—S2—C14	107.5 (3)	O3—C9—C8	110.0 (5)
O6—S2—C14	108.2 (3)	C11—C10—H10A	109.5
N2—S2—C14	107.8 (3)	C11—C10—H10B	109.5
C9—O3—H3	109.5	H10A—C10—H10B	109.5
C18—O7—H7	109.5	C11—C10—H10C	109.5
C8—N1—S1	117.0 (4)	H10A—C10—H10C	109.5
C8—N1—H1	121.5	H10B—C10—H10C	109.5
S1—N1—H1	121.5	C16—C11—C12	117.6 (6)
C17—N2—S2	117.2 (4)	C16—C11—C10	121.3 (6)
C17—N2—H2	121.4	C12—C11—C10	121.1 (6)
S2—N2—H2	121.4	C13—C12—C11	121.8 (6)
C2—C1—H1A	109.5	C13—C12—H12	119.1
C2—C1—H1B	109.5	C11—C12—H12	119.1
H1A—C1—H1B	109.5	C12—C13—C14	119.2 (6)
C2—C1—H1C	109.5	C12—C13—H13	120.4
H1A—C1—H1C	109.5	C14—C13—H13	120.4
H1B—C1—H1C	109.5	C15—C14—C13	120.4 (6)
C7—C2—C3	116.7 (6)	C15—C14—S2	119.4 (5)
C7—C2—C1	122.4 (6)	C13—C14—S2	120.0 (5)
C3—C2—C1	120.9 (6)	C16—C15—C14	118.6 (6)
C4—C3—C2	122.0 (6)	C16—C15—H15	120.7
C4—C3—H3A	119.0	C14—C15—H15	120.7
C2—C3—H3A	119.0	C11—C16—C15	122.3 (6)
C3—C4—C5	119.0 (6)	C11—C16—H16	118.9
C3—C4—H4	120.5	C15—C16—H16	118.9
C5—C4—H4	120.5	N2—C17—C18	113.2 (5)
C6—C5—C4	120.4 (6)	N2—C17—H17A	108.9
C6—C5—S1	120.9 (5)	C18—C17—H17A	108.9
C4—C5—S1	118.7 (5)	N2—C17—H17B	108.9
C5—C6—C7	119.0 (6)	C18—C17—H17B	108.9
C5—C6—H6	120.5	H17A—C17—H17B	107.8
C7—C6—H6	120.5	O8—C18—O7	124.0 (6)
C6—C7—C2	122.8 (6)	O8—C18—C17	125.4 (6)
C6—C7—H7A	118.6	O7—C18—C17	110.6 (6)

O2—S1—N1—C8	52.6 (5)	S1—N1—C8—C9	−93.0 (5)
O1—S1—N1—C8	−177.8 (4)	N1—C8—C9—O4	−8.0 (9)
C5—S1—N1—C8	−61.8 (5)	N1—C8—C9—O3	171.5 (5)
O5—S2—N2—C17	−51.9 (5)	C16—C11—C12—C13	−0.6 (10)
O6—S2—N2—C17	178.9 (5)	C10—C11—C12—C13	179.8 (6)
C14—S2—N2—C17	63.2 (5)	C11—C12—C13—C14	0.1 (10)
C7—C2—C3—C4	−0.8 (9)	C12—C13—C14—C15	−0.3 (9)
C1—C2—C3—C4	−180.0 (6)	C12—C13—C14—S2	175.8 (5)
C2—C3—C4—C5	1.8 (9)	O5—S2—C14—C15	−12.0 (6)
C3—C4—C5—C6	−1.0 (9)	O6—S2—C14—C15	119.3 (5)
C3—C4—C5—S1	−179.0 (5)	N2—S2—C14—C15	−126.4 (5)
O2—S1—C5—C6	10.9 (6)	O5—S2—C14—C13	171.9 (5)
O1—S1—C5—C6	−120.8 (5)	O6—S2—C14—C13	−56.8 (6)
N1—S1—C5—C6	124.8 (5)	N2—S2—C14—C13	57.5 (6)
O2—S1—C5—C4	−171.1 (5)	C13—C14—C15—C16	1.0 (10)
O1—S1—C5—C4	57.2 (5)	S2—C14—C15—C16	−175.1 (5)
N1—S1—C5—C4	−57.3 (5)	C12—C11—C16—C15	1.3 (10)
C4—C5—C6—C7	−0.6 (9)	C10—C11—C16—C15	−179.1 (6)
S1—C5—C6—C7	177.3 (5)	C14—C15—C16—C11	−1.5 (10)
C5—C6—C7—C2	1.7 (10)	S2—N2—C17—C18	82.7 (6)
C3—C2—C7—C6	−1.0 (10)	N2—C17—C18—O8	22.6 (9)
C1—C2—C7—C6	178.2 (6)	N2—C17—C18—O7	−158.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.86	2.57	3.167 (6)	127
N2—H2···O8ⁱⁱ	0.86	2.59	3.231 (7)	132
O3—H3···O4ⁱⁱⁱ	0.82	1.94	2.751 (6)	172
O7—H7···O8^iv	0.82	1.94	2.745 (7)	167
C1—H1B···O5^v	0.96	2.56	3.342 (7)	138
C10—H10B···O2^vi	0.96	2.40	3.353 (7)	170
C17—H17B···O6ⁱⁱ	0.97	2.45	3.211 (6)	134

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

Experimental details

Crystal data
Chemical formula	C₉H₁₁NO₄S
M_r	229.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	22.3240 (19), 5.7263 (5), 16.5526 (14)
β (°)	109.069 (2)
V (Å³)	1999.9 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.27 × 0.13 × 0.11

Data collection
Diffractometer	Bruker APEX area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.919, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	9980, 3524, 2969
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.114, 1.29
No. of reflections	3524
No. of parameters	275
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.41

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXL97.

Selected geometric parameters (Å, º) top

S1—O2	1.413 (4)	S1—N1	1.625 (5)
S1—O1	1.429 (4)	S1—C5	1.769 (6)

O2—S1—O1	120.4 (3)	O2—S1—C5	107.3 (3)
O2—S1—N1	106.4 (3)	O1—S1—C5	108.6 (3)
O1—S1—N1	106.4 (3)	N1—S1—C5	107.0 (3)