(E)-4-[(2-Hydroxy­benzyl­idene)amino]benzene­sulfonic acid

Zhang, X.; Li, Z.

doi:10.1107/S1600536808015407

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1159

doi:10.1107/S1600536808015407

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(E)-4-[(2-Hydroxybenzylidene)amino]benzenesulfonic acid

Xinli Zhang ^a and Zongxiao Li ^a ^*

^aDepartment of Chemistry, Baoji University of Arts and Science, Baoji, Shaanxi 721007, People's Republic of China
^*Correspondence e-mail: mingtian8001@163.com

(Received 4 May 2008; accepted 22 May 2008; online 30 May 2008)

The title molecule, C₁₃H₁₁NO₄S, displays a trans configuration with respect to the imine C=N double bond. The central benzene ring directly linked to N and the hydroxyl group are disordered over two orientations [occupancies of 0.510 (16)/0.490 (16) and 0.528 (8)/0.472 (8), respectively]. The dihedral angle between the two aromatic rings is 23.3 (5)° for the major component and 18.3 (5)° for the minor component. There is an intramolecular O—H⋯N hydrogen bond and molecules are linked into chains along the a axis by O—H⋯O hydrogen bonds.

Related literature

For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₃H₁₁NO₄S
M_r = 277.29
Monoclinic, C c
a = 4.8711 (5) Å
b = 29.022 (3) Å
c = 9.0356 (17) Å
β = 97.223 (2)°
V = 1267.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 298 (2) K
0.42 × 0.31 × 0.15 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.897, T_max = 0.961
3185 measured reflections
1952 independent reflections
1656 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.121
S = 1.09
1952 reflections
213 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ), 822 Friedel pairs
Flack parameter: −0.06 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3ⁱ	0.82	2.17	2.917 (5)	151
O4—H4⋯N1	0.82	2.01	2.665 (10)	136
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808015407/ci2596sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015407/ci2596Isup2.hkl

checkCIF report

Comment top

Schiff base compounds have been of great interest for many years. These compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures. As an extension of the work on the structural characterization of Schiff base compounds, the crystal structure of the title compound is reported here.

The structure of the title molecule is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987). The C7═N1 bond length of 1.262 (7) Å conforms to the value for a double bond. The dihedral angle between C1—C6 and C8—C13 benzene rings is 23.3 (5)° and that between C1/C2'/C3'/C4/C5'/C6' and C8—C13 rings is 18.3 (5)°. The C7—N1—C4—C5, C7—N1—C4—C3, O1—S1—C1—C6, O3—S1—C1—C6 and O2—S1—C1—C6 torsion angles are 22.8 (12)°, -156.4 (9)°, 173.5 (9)°, -58.9 (9)° and 56.3 (9)°, respectively. The molecule adopts a trans configuration about the C7?N1 bond. There exists an intramolecular O4—H4···N1 hydrogen bond involving the hydroxyl group and the imine N atom (Table 1).

In the crystal structure, the molecules are linked into chains running along the a axis by O—H···O hydrogen bonds.

Related literature top

For bond-length data, see: Allen et al. (1987).

Experimental top

Salicylaldehyde (0.1 mmol, 12.2 mg) and sulfamide (0.1 mmol, 17.2 mg) were dissolved in methanol (10 ml). The mixture was stirred at room temperature for 10 min and then filtered. The filtrate was allowed to stand in air for 3 d, after which time yellow block-shaped crystals of the title compound were formed by slow evaporation of the solvent. The crystals were collected, washed with methanol and dried in a vacuum desiccator using anhydrous CaCl₂ (yield 54%). Analysis found: C 48.88, H 3.20, N 4.07%; calculated for C₁₃H₁₁NO₄S: C 48.9, H 3.20, N 4.08%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Both disorder components are shown.

(E)-4-[(2-Hydroxybenzylidene)amino]benzenesulfonic acid top

Crystal data top

C₁₃H₁₁NO₄S	F(000) = 576
M_r = 277.29	D_x = 1.453 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1329 reflections
a = 4.8711 (5) Å	θ = 2.7–23.9°
b = 29.022 (3) Å	µ = 0.27 mm⁻¹
c = 9.0356 (17) Å	T = 298 K
β = 97.223 (2)°	Block, yellow
V = 1267.2 (3) Å³	0.42 × 0.31 × 0.15 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	1952 independent reflections
Radiation source: fine-focus sealed tube	1656 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
T_min = 0.897, T_max = 0.961	k = −34→31
3185 measured reflections	l = −9→10

Refinement top

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)] = 0.050	H-atom parameters constrained
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.0495P)² + 1.7913P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
1952 reflections	Δρ_max = 0.34 e Å⁻³
213 parameters	Δρ_min = −0.30 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 822 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (14)

Crystal data top

C₁₃H₁₁NO₄S	V = 1267.2 (3) Å³
M_r = 277.29	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 4.8711 (5) Å	µ = 0.27 mm⁻¹
b = 29.022 (3) Å	T = 298 K
c = 9.0356 (17) Å	0.42 × 0.31 × 0.15 mm
β = 97.223 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	1952 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1656 reflections with I > 2σ(I)
T_min = 0.897, T_max = 0.961	R_int = 0.026
3185 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.121	Δρ_max = 0.34 e Å⁻³
S = 1.09	Δρ_min = −0.30 e Å⁻³
1952 reflections	Absolute structure: Flack (1983), 822 Friedel pairs
213 parameters	Absolute structure parameter: −0.06 (14)
2 restraints

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	Occ. (<1)
S1	0.75870 (18)	0.76105 (3)	0.47671 (13)	0.0372 (3)
N1	0.6129 (9)	0.96320 (13)	0.4070 (4)	0.0490 (10)
O1	0.6035 (6)	0.73963 (10)	0.3515 (3)	0.0470 (8)
O2	0.6306 (8)	0.74475 (13)	0.6247 (5)	0.0663 (11)
H2	0.4678	0.7526	0.6185	0.099*
O3	1.0490 (7)	0.75204 (11)	0.5021 (4)	0.0501 (8)
O4	0.387 (2)	1.0337 (3)	0.2463 (11)	0.0675 (18)	0.528 (8)
H4	0.4579	1.0080	0.2483	0.101*	0.528 (8)
O4'	0.285 (2)	1.0279 (4)	0.3133 (12)	0.0675 (18)	0.472 (8)
H4'	0.3138	1.0031	0.3557	0.101*	0.472 (8)
C1	0.7196 (9)	0.82135 (14)	0.4573 (5)	0.0365 (11)
C2	0.585 (3)	0.8377 (3)	0.3264 (16)	0.042 (3)	0.510 (16)
H2A	0.5178	0.8179	0.2493	0.051*	0.510 (16)
C3	0.554 (3)	0.8837 (3)	0.3133 (16)	0.045 (3)	0.510 (16)
H3	0.4598	0.8955	0.2254	0.055*	0.510 (16)
C2'	0.470 (3)	0.8413 (3)	0.3925 (16)	0.042 (3)	0.490 (16)
H2'	0.3224	0.8223	0.3586	0.051*	0.490 (16)
C3'	0.439 (3)	0.8887 (3)	0.3777 (16)	0.044 (3)	0.490 (16)
H3'	0.2733	0.9015	0.3339	0.053*	0.490 (16)
C4	0.6589 (11)	0.91570 (17)	0.4298 (6)	0.0426 (11)
C5	0.805 (3)	0.8949 (4)	0.5579 (16)	0.046 (3)	0.510 (16)
H5	0.8868	0.9136	0.6346	0.056*	0.510 (16)
C6	0.829 (3)	0.8473 (4)	0.5726 (16)	0.043 (3)	0.510 (16)
H6	0.9179	0.8339	0.6592	0.052*	0.510 (16)
C5'	0.909 (3)	0.8993 (4)	0.4909 (19)	0.047 (3)	0.490 (16)
H5'	1.0547	0.9193	0.5213	0.056*	0.490 (16)
C6'	0.941 (3)	0.8522 (4)	0.5065 (17)	0.047 (3)	0.490 (16)
H6'	1.1100	0.8403	0.5497	0.057*	0.490 (16)
C7	0.7682 (15)	0.99282 (16)	0.4771 (9)	0.0655 (13)
H7	0.9180	0.9826	0.5429	0.079*
C8	0.7245 (14)	1.04208 (16)	0.4601 (8)	0.0570 (14)
C9	0.5144 (14)	1.0594 (2)	0.3606 (8)	0.0771 (19)
C10	0.488 (2)	1.1068 (2)	0.3501 (10)	0.107 (3)
H10	0.3437	1.1187	0.2843	0.129*
C11	0.6584 (18)	1.1363 (2)	0.4287 (9)	0.0768 (18)
H11	0.6321	1.1679	0.4172	0.092*
C12	0.863 (2)	1.1202 (2)	0.5224 (11)	0.102 (3)
H12	0.9840	1.1404	0.5776	0.122*
C13	0.8992 (19)	1.0729 (2)	0.5393 (10)	0.111 (3)
H13	1.0455	1.0618	0.6059	0.133*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0310 (6)	0.0410 (5)	0.0369 (5)	0.0050 (6)	−0.0055 (4)	−0.0024 (6)
N1	0.052 (3)	0.041 (2)	0.054 (3)	−0.0006 (18)	0.008 (2)	0.0014 (18)
O1	0.048 (2)	0.0473 (18)	0.0402 (19)	0.0021 (15)	−0.0139 (15)	−0.0081 (15)
O2	0.055 (2)	0.072 (2)	0.070 (3)	0.0037 (18)	0.0028 (19)	0.0086 (19)
O3	0.0328 (18)	0.057 (2)	0.060 (2)	0.0086 (14)	0.0027 (15)	−0.0050 (16)
O4	0.076 (6)	0.062 (3)	0.062 (5)	0.009 (3)	−0.001 (3)	0.008 (4)
O4'	0.076 (6)	0.062 (3)	0.062 (5)	0.009 (3)	−0.001 (3)	0.008 (4)
C1	0.032 (3)	0.040 (2)	0.037 (3)	0.002 (2)	0.003 (2)	0.000 (2)
C2	0.047 (8)	0.039 (6)	0.039 (7)	−0.008 (5)	−0.001 (6)	−0.005 (5)
C3	0.047 (7)	0.045 (6)	0.043 (7)	0.002 (5)	0.001 (6)	0.002 (5)
C2'	0.036 (7)	0.041 (6)	0.047 (8)	−0.004 (5)	−0.004 (6)	−0.004 (5)
C3'	0.044 (7)	0.042 (6)	0.046 (7)	0.005 (5)	0.004 (6)	0.000 (5)
C4	0.041 (3)	0.040 (3)	0.046 (3)	−0.002 (2)	0.005 (2)	−0.001 (2)
C5	0.057 (9)	0.041 (6)	0.042 (7)	0.002 (5)	0.007 (6)	−0.008 (5)
C6	0.048 (8)	0.042 (6)	0.036 (7)	0.002 (5)	−0.003 (6)	−0.007 (5)
C5'	0.041 (8)	0.042 (6)	0.056 (9)	−0.003 (5)	0.004 (7)	−0.008 (6)
C6'	0.037 (8)	0.046 (7)	0.057 (9)	0.003 (5)	0.000 (7)	−0.003 (6)
C7	0.069 (3)	0.048 (3)	0.075 (3)	−0.001 (4)	−0.010 (3)	0.009 (4)
C8	0.064 (4)	0.042 (2)	0.066 (4)	−0.006 (3)	0.013 (3)	0.002 (3)
C9	0.083 (5)	0.051 (3)	0.091 (5)	0.019 (3)	−0.014 (4)	−0.018 (3)
C10	0.125 (7)	0.058 (4)	0.126 (7)	0.030 (4)	−0.035 (6)	−0.003 (4)
C11	0.105 (6)	0.046 (3)	0.084 (5)	0.006 (4)	0.027 (4)	−0.004 (3)
C12	0.118 (7)	0.056 (4)	0.125 (7)	−0.021 (5)	−0.012 (6)	0.001 (5)
C13	0.120 (6)	0.058 (4)	0.139 (7)	−0.013 (4)	−0.042 (6)	0.010 (5)

Geometric parameters (Å, º) top

S1—O1	1.422 (3)	C3'—H3'	0.93
S1—O3	1.428 (3)	C4—C5'	1.359 (15)
S1—O2	1.615 (4)	C4—C5	1.415 (14)
S1—C1	1.767 (4)	C5—C6	1.392 (15)
N1—C7	1.262 (7)	C5—H5	0.93
N1—C4	1.408 (6)	C6—H6	0.93
O2—H2	0.82	C5'—C6'	1.382 (15)
O4—C9	1.359 (10)	C5'—H5'	0.93
O4—H4	0.82	C6'—H6'	0.93
O4'—C9	1.465 (12)	C7—C8	1.451 (6)
O4'—H4'	0.82	C7—H7	0.93
C1—C6	1.340 (11)	C8—C9	1.370 (8)
C1—C2	1.363 (12)	C8—C13	1.372 (9)
C1—C2'	1.405 (12)	C9—C10	1.382 (8)
C1—C6'	1.430 (13)	C10—C11	1.333 (11)
C2—C3	1.348 (13)	C10—H10	0.93
C2—H2A	0.93	C11—C12	1.310 (10)
C3—C4	1.448 (13)	C11—H11	0.93
C3—H3	0.93	C12—C13	1.390 (9)
C2'—C3'	1.387 (14)	C12—H12	0.93
C2'—H2'	0.93	C13—H13	0.93
C3'—C4	1.364 (12)

O1—S1—O3	117.6 (2)	C5—C4—C3	114.6 (7)
O1—S1—O2	108.0 (2)	C6—C5—C4	122.0 (10)
O3—S1—O2	106.9 (2)	C6—C5—H5	119.0
O1—S1—C1	108.29 (19)	C4—C5—H5	119.0
O3—S1—C1	106.8 (2)	C1—C6—C5	117.5 (10)
O2—S1—C1	108.9 (2)	C1—C6—H6	121.2
C7—N1—C4	121.3 (4)	C5—C6—H6	121.2
S1—O2—H2	109.5	C4—C5'—C6'	118.2 (11)
C9—O4—H4	109.5	C4—C5'—H5'	120.9
C9—O4'—H4'	109.5	C6'—C5'—H5'	120.9
C6—C1—C2	125.4 (8)	C5'—C6'—C1	121.1 (11)
C6—C1—C2'	109.3 (8)	C5'—C6'—H6'	119.5
C2—C1—C6'	108.3 (7)	C1—C6'—H6'	119.5
C2'—C1—C6'	116.8 (7)	N1—C7—C8	123.2 (6)
C6—C1—S1	116.8 (6)	N1—C7—H7	118.4
C2—C1—S1	117.7 (5)	C8—C7—H7	118.4
C2'—C1—S1	121.8 (5)	C9—C8—C13	117.8 (6)
C6'—C1—S1	121.4 (5)	C9—C8—C7	121.3 (6)
C3—C2—C1	117.3 (10)	C13—C8—C7	120.9 (6)
C3—C2—H2A	121.4	O4—C9—C8	121.9 (6)
C1—C2—H2A	121.4	O4—C9—C10	117.7 (7)
C2—C3—C4	123.0 (10)	C8—C9—C10	117.7 (6)
C2—C3—H3	118.5	C8—C9—O4'	116.2 (6)
C4—C3—H3	118.5	C10—C9—O4'	122.7 (7)
C3'—C2'—C1	121.9 (9)	C11—C10—C9	123.8 (7)
C3'—C2'—H2'	119.0	C11—C10—H10	118.1
C1—C2'—H2'	119.0	C9—C10—H10	118.1
C4—C3'—C2'	117.6 (10)	C12—C11—C10	119.1 (7)
C4—C3'—H3'	121.2	C12—C11—H11	120.5
C2'—C3'—H3'	121.2	C10—C11—H11	120.5
C5'—C4—C3'	124.4 (8)	C11—C12—C13	119.9 (8)
C5'—C4—N1	121.3 (6)	C11—C12—H12	120.0
C3'—C4—N1	114.1 (6)	C13—C12—H12	120.0
C3'—C4—C5	109.2 (8)	C8—C13—C12	121.7 (8)
N1—C4—C5	126.3 (6)	C8—C13—H13	119.2
C5'—C4—C3	106.8 (8)	C12—C13—H13	119.2
N1—C4—C3	119.1 (6)

O1—S1—C1—C6	173.5 (9)	C3'—C4—C5—C6	34.7 (15)
O3—S1—C1—C6	−58.9 (9)	N1—C4—C5—C6	177.2 (9)
O2—S1—C1—C6	56.3 (9)	C3—C4—C5—C6	−3.6 (16)
O1—S1—C1—C2	−7.4 (9)	C2—C1—C6—C5	−0.2 (17)
O3—S1—C1—C2	120.2 (8)	C2'—C1—C6—C5	−37.8 (14)
O2—S1—C1—C2	−124.6 (8)	C6'—C1—C6—C5	71.4 (15)
O1—S1—C1—C2'	35.0 (9)	S1—C1—C6—C5	178.8 (9)
O3—S1—C1—C2'	162.6 (8)	C4—C5—C6—C1	3.0 (18)
O2—S1—C1—C2'	−82.2 (9)	C3'—C4—C5'—C6'	−2.4 (19)
O1—S1—C1—C6'	−144.8 (9)	N1—C4—C5'—C6'	−178.4 (10)
O3—S1—C1—C6'	−17.2 (9)	C5—C4—C5'—C6'	71.8 (15)
O2—S1—C1—C6'	98.0 (9)	C3—C4—C5'—C6'	−37.3 (15)
C6—C1—C2—C3	−1.7 (17)	C4—C5'—C6'—C1	1 (2)
C2'—C1—C2—C3	72.3 (14)	C6—C1—C6'—C5'	−86.4 (17)
C6'—C1—C2—C3	−38.2 (14)	C2—C1—C6'—C5'	39.1 (16)
S1—C1—C2—C3	179.3 (9)	C2'—C1—C6'—C5'	0.2 (17)
C1—C2—C3—C4	1.0 (18)	S1—C1—C6'—C5'	180.0 (10)
C6—C1—C2'—C3'	38.5 (15)	C4—N1—C7—C8	−178.4 (6)
C2—C1—C2'—C3'	−85.4 (15)	N1—C7—C8—C9	−2.7 (11)
C6'—C1—C2'—C3'	−0.5 (16)	N1—C7—C8—C13	179.9 (8)
S1—C1—C2'—C3'	179.7 (9)	C13—C8—C9—O4	159.1 (9)
C1—C2'—C3'—C4	−0.6 (17)	C7—C8—C9—O4	−18.5 (11)
C2'—C3'—C4—C5'	2.1 (17)	C13—C8—C9—C10	−1.8 (11)
C2'—C3'—C4—N1	178.4 (9)	C7—C8—C9—C10	−179.4 (8)
C2'—C3'—C4—C5	−34.2 (14)	C13—C8—C9—O4'	−161.6 (8)
C2'—C3'—C4—C3	71.5 (13)	C7—C8—C9—O4'	20.9 (11)
C7—N1—C4—C5'	−19.9 (12)	O4—C9—C10—C11	−160.3 (10)
C7—N1—C4—C3'	163.7 (9)	C8—C9—C10—C11	1.4 (14)
C7—N1—C4—C5	22.8 (12)	O4'—C9—C10—C11	159.7 (10)
C7—N1—C4—C3	−156.4 (9)	C9—C10—C11—C12	−0.2 (15)
C2—C3—C4—C5'	38.7 (16)	C10—C11—C12—C13	−0.4 (14)
C2—C3—C4—C3'	−87.5 (16)	C9—C8—C13—C12	1.3 (13)
C2—C3—C4—N1	−179.1 (10)	C7—C8—C13—C12	178.9 (9)
C2—C3—C4—C5	1.5 (17)	C11—C12—C13—C8	−0.2 (14)
C5'—C4—C5—C6	−88.1 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.82	2.17	2.917 (5)	151
O4—H4···N1	0.82	2.01	2.665 (10)	136

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁NO₄S
M_r	277.29
Crystal system, space group	Monoclinic, Cc
Temperature (K)	298
a, b, c (Å)	4.8711 (5), 29.022 (3), 9.0356 (17)
β (°)	97.223 (2)
V (Å³)	1267.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.42 × 0.31 × 0.15

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.897, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	3185, 1952, 1656
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.121, 1.09
No. of reflections	1952
No. of parameters	213
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.30
Absolute structure	Flack (1983), 822 Friedel pairs
Absolute structure parameter	−0.06 (14)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.82	2.17	2.917 (5)	151
O4—H4···N1	0.82	2.01	2.665 (10)	136

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors are grateful for research grant No. 02js40 from the Phytochemistry Key Laboratory of Shaanxi Province.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar