3-Hy-droxy-2-(4-meth-oxy-benzene-sulfonamido)-butanoic acid.

The title compound, C(11)H(15)NO(6)S, features a distorted tetra-hedral geometry for the S atom. One of the sulfonamide O atoms is approximately coplanar with the benzene ring [C-C-S-O torsion angle = -160.81 (7)°], whereas the other lies well below the plane [C-C-S-O = -29.66 (8)°]. In the crystal, O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into chains parallel to the b axis.

Related literature

For details and applications of sulfonamides, see: Supuran et al. (2003 ▶); Scozzafava et al. (2003 ▶); Robinson et al. (2003 ▶); Delaet et al. (2003 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C11H15NO6S

M = 289.30

Orthorhombic,

a = 5.6505 (2) Å

b = 9.9204 (3) Å

c = 23.0561 (6) Å

V = 1292.41 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.75 × 0.19 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.821, T max = 0.954

35154 measured reflections

5756 independent reflections

5505 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.073

S = 1.07

5756 reflections

186 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.42 e Å−3

Absolute structure: Flack (1983 ▶), 2444 Friedel pairs

Flack parameter: 0.02 (4)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046502/rz2664sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046502/rz2664Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046502/rz2664Isup3.cml

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

C11H15NO6S	F(000) = 608
Mr = 289.30	Dx = 1.487 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9845 reflections
a = 5.6505 (2) Å	θ = 3.4–35.2°
b = 9.9204 (3) Å	µ = 0.27 mm−1
c = 23.0561 (6) Å	T = 100 K
V = 1292.41 (7) Å3	Block, colourless
Z = 4	0.75 × 0.19 × 0.17 mm

Bruker SMART APEXII CCD area-detector diffractometer	5756 independent reflections
Radiation source: fine-focus sealed tube	5505 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 35.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→9
Tmin = 0.821, Tmax = 0.954	k = −16→16
35154 measured reflections	l = −37→37

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.073	w = 1/[σ2(Fo2) + (0.0407P)2 + 0.163P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
5756 reflections	Δρmax = 0.34 e Å−3
186 parameters	Δρmin = −0.42 e Å−3
0 restraints	Absolute structure: Flack (1983), 2444 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (4)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 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
S1	0.72919 (4)	0.22850 (2)	0.138337 (9)	0.01332 (4)
O1	0.78573 (15)	0.61425 (7)	−0.05450 (3)	0.02057 (13)
O2	0.48689 (13)	0.21583 (8)	0.15597 (3)	0.01902 (13)
O3	0.86556 (14)	0.10991 (7)	0.12458 (3)	0.01897 (13)
O4	1.15328 (13)	0.52453 (7)	0.17150 (3)	0.02082 (14)
O5	0.85821 (13)	0.66432 (7)	0.19810 (4)	0.01992 (14)
O6	0.96165 (12)	0.40568 (7)	0.30315 (3)	0.01456 (11)
N1	0.87145 (14)	0.30287 (7)	0.19112 (3)	0.01372 (12)
C1	0.93213 (15)	0.33833 (9)	0.04102 (4)	0.01481 (14)
H1A	1.0550	0.2771	0.0462	0.018*
C2	0.94041 (16)	0.43159 (9)	−0.00357 (4)	0.01560 (14)
H2A	1.0688	0.4326	−0.0288	0.019*
C3	0.75624 (17)	0.52429 (8)	−0.01084 (3)	0.01491 (14)
C4	0.56040 (16)	0.52178 (10)	0.02592 (4)	0.01660 (15)
H4A	0.4368	0.5824	0.0206	0.020*
C5	0.55119 (15)	0.42778 (9)	0.07069 (4)	0.01495 (14)
H5A	0.4214	0.4255	0.0955	0.018*
C6	0.73634 (15)	0.33731 (8)	0.07829 (3)	0.01262 (12)
C7	0.78523 (15)	0.43593 (8)	0.20919 (4)	0.01261 (13)
H7A	0.6333	0.4522	0.1899	0.015*
C8	0.74478 (15)	0.44309 (8)	0.27510 (3)	0.01324 (13)
H8A	0.7047	0.5359	0.2858	0.016*
C9	0.54836 (17)	0.35081 (11)	0.29434 (4)	0.02040 (17)
H9A	0.5260	0.3595	0.3354	0.031*
H9B	0.5891	0.2593	0.2852	0.031*
H9C	0.4047	0.3748	0.2747	0.031*
C10	0.95658 (16)	0.54537 (9)	0.19018 (4)	0.01371 (14)
C11	0.6019 (2)	0.71196 (10)	−0.06293 (4)	0.02317 (19)
H11A	0.6467	0.7728	−0.0934	0.035*
H11B	0.5782	0.7616	−0.0277	0.035*
H11C	0.4578	0.6668	−0.0734	0.035*
H1N1	1.025 (3)	0.3010 (15)	0.1834 (7)	0.025 (4)*
H1O5	0.952 (3)	0.7296 (19)	0.1933 (8)	0.039 (5)*
H1O6	1.008 (4)	0.462 (2)	0.3261 (9)	0.059 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.01979 (8)	0.00881 (7)	0.01137 (8)	−0.00184 (7)	−0.00180 (7)	0.00073 (6)
O1	0.0300 (3)	0.0169 (3)	0.0149 (3)	0.0028 (3)	0.0028 (3)	0.0051 (2)
O2	0.0214 (3)	0.0182 (3)	0.0175 (3)	−0.0080 (3)	0.0000 (2)	0.0032 (2)
O3	0.0322 (4)	0.0089 (2)	0.0157 (3)	0.0027 (3)	−0.0047 (3)	−0.0007 (2)
O4	0.0202 (3)	0.0154 (3)	0.0269 (3)	0.0005 (2)	0.0100 (3)	0.0002 (3)
O5	0.0183 (3)	0.0094 (3)	0.0321 (4)	0.0004 (2)	0.0039 (3)	0.0003 (3)
O6	0.0156 (2)	0.0127 (3)	0.0154 (3)	−0.0003 (2)	−0.0030 (2)	−0.0036 (2)
N1	0.0178 (3)	0.0104 (3)	0.0130 (3)	0.0009 (2)	−0.0027 (2)	−0.0016 (2)
C1	0.0166 (3)	0.0127 (3)	0.0151 (3)	0.0023 (3)	0.0001 (3)	−0.0012 (3)
C2	0.0184 (3)	0.0147 (3)	0.0137 (3)	0.0010 (3)	0.0032 (3)	−0.0002 (3)
C3	0.0209 (3)	0.0123 (3)	0.0115 (3)	0.0005 (3)	0.0006 (3)	0.0010 (2)
C4	0.0181 (4)	0.0163 (4)	0.0153 (4)	0.0037 (3)	0.0000 (3)	0.0035 (3)
C5	0.0151 (3)	0.0158 (3)	0.0139 (3)	0.0013 (3)	0.0007 (3)	0.0014 (3)
C6	0.0159 (3)	0.0107 (3)	0.0113 (3)	0.0000 (3)	−0.0006 (3)	0.0007 (2)
C7	0.0147 (3)	0.0097 (3)	0.0135 (3)	0.0002 (3)	−0.0003 (3)	−0.0006 (2)
C8	0.0129 (3)	0.0135 (3)	0.0133 (3)	0.0009 (3)	0.0010 (3)	−0.0013 (2)
C9	0.0155 (3)	0.0252 (4)	0.0206 (4)	−0.0034 (3)	0.0036 (3)	0.0027 (3)
C10	0.0163 (3)	0.0113 (3)	0.0136 (3)	0.0005 (3)	0.0007 (3)	0.0002 (3)
C11	0.0355 (5)	0.0165 (4)	0.0175 (4)	0.0033 (4)	−0.0036 (4)	0.0037 (3)

S1—O2	1.4337 (8)	C2—H2A	0.9300
S1—O3	1.4416 (7)	C3—C4	1.3940 (13)
S1—N1	1.6345 (8)	C4—C5	1.3922 (12)
S1—C6	1.7561 (8)	C4—H4A	0.9300
O1—C3	1.3555 (10)	C5—C6	1.3895 (12)
O1—C11	1.4338 (13)	C5—H5A	0.9300
O4—C10	1.2097 (11)	C7—C10	1.5193 (12)
O5—C10	1.3171 (11)	C7—C8	1.5385 (11)
O5—H1O5	0.845 (19)	C7—H7A	0.9800
O6—C8	1.4344 (11)	C8—C9	1.5055 (13)
O6—H1O6	0.81 (2)	C8—H8A	0.9800
N1—C7	1.4674 (11)	C9—H9A	0.9600
N1—H1N1	0.887 (17)	C9—H9B	0.9600
C1—C2	1.3839 (13)	C9—H9C	0.9600
C1—C6	1.4008 (12)	C11—H11A	0.9600
C1—H1A	0.9300	C11—H11B	0.9600
C2—C3	1.3989 (13)	C11—H11C	0.9600
O2—S1—O3	120.08 (5)	C1—C6—S1	120.41 (6)
O2—S1—N1	107.35 (4)	N1—C7—C10	110.45 (7)
O3—S1—N1	105.62 (4)	N1—C7—C8	111.80 (7)
O2—S1—C6	107.42 (4)	C10—C7—C8	110.28 (7)
O3—S1—C6	108.41 (4)	N1—C7—H7A	108.1
N1—S1—C6	107.35 (4)	C10—C7—H7A	108.1
C3—O1—C11	117.17 (8)	C8—C7—H7A	108.1
C10—O5—H1O5	113.7 (13)	O6—C8—C9	109.86 (7)
C8—O6—H1O6	113.2 (16)	O6—C8—C7	107.85 (7)
C7—N1—S1	117.01 (6)	C9—C8—C7	111.87 (7)
C7—N1—H1N1	113.6 (10)	O6—C8—H8A	109.1
S1—N1—H1N1	108.9 (10)	C9—C8—H8A	109.1
C2—C1—C6	119.16 (8)	C7—C8—H8A	109.1
C2—C1—H1A	120.4	C8—C9—H9A	109.5
C6—C1—H1A	120.4	C8—C9—H9B	109.5
C1—C2—C3	120.23 (8)	H9A—C9—H9B	109.5
C1—C2—H2A	119.9	C8—C9—H9C	109.5
C3—C2—H2A	119.9	H9A—C9—H9C	109.5
O1—C3—C4	124.11 (8)	H9B—C9—H9C	109.5
O1—C3—C2	115.49 (8)	O4—C10—O5	126.17 (9)
C4—C3—C2	120.39 (8)	O4—C10—C7	124.47 (8)
C5—C4—C3	119.50 (8)	O5—C10—C7	109.35 (7)
C5—C4—H4A	120.2	O1—C11—H11A	109.5
C3—C4—H4A	120.2	O1—C11—H11B	109.5
C6—C5—C4	119.87 (8)	H11A—C11—H11B	109.5
C6—C5—H5A	120.1	O1—C11—H11C	109.5
C4—C5—H5A	120.1	H11A—C11—H11C	109.5
C5—C6—C1	120.84 (8)	H11B—C11—H11C	109.5
C5—C6—S1	118.63 (6)
O2—S1—N1—C7	−57.73 (7)	O3—S1—C6—C5	154.30 (7)
O3—S1—N1—C7	173.03 (6)	N1—S1—C6—C5	−92.03 (7)
C6—S1—N1—C7	57.50 (7)	O2—S1—C6—C1	−160.81 (7)
C6—C1—C2—C3	0.59 (13)	O3—S1—C6—C1	−29.66 (8)
C11—O1—C3—C4	−0.22 (13)	N1—S1—C6—C1	84.01 (8)
C11—O1—C3—C2	−179.31 (8)	S1—N1—C7—C10	−108.33 (7)
C1—C2—C3—O1	177.73 (8)	S1—N1—C7—C8	128.47 (6)
C1—C2—C3—C4	−1.40 (14)	N1—C7—C8—O6	55.38 (9)
O1—C3—C4—C5	−177.88 (9)	C10—C7—C8—O6	−67.91 (8)
C2—C3—C4—C5	1.17 (14)	N1—C7—C8—C9	−65.53 (9)
C3—C4—C5—C6	−0.15 (14)	C10—C7—C8—C9	171.18 (7)
C4—C5—C6—C1	−0.66 (13)	N1—C7—C10—O4	−11.26 (12)
C4—C5—C6—S1	175.37 (7)	C8—C7—C10—O4	112.81 (10)
C2—C1—C6—C5	0.43 (13)	N1—C7—C10—O5	169.63 (7)
C2—C1—C6—S1	−175.52 (7)	C8—C7—C10—O5	−66.30 (9)
O2—S1—C6—C5	23.15 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1O5···O6i	0.844 (18)	1.816 (19)	2.6019 (10)	154.3 (17)
O6—H1O6···O3i	0.81 (2)	1.99 (2)	2.7990 (10)	174.2 (19)
C5—H5A···O4ii	0.93	2.52	3.3732 (11)	153.
C8—H8A···O2iii	0.98	2.48	3.4000 (11)	156.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1O5⋯O6i	0.844 (18)	1.816 (19)	2.6019 (10)	154.3 (17)
O6—H1O6⋯O3i	0.81 (2)	1.99 (2)	2.7990 (10)	174.2 (19)
C5—H5A⋯O4ii	0.93	2.52	3.3732 (11)	153
C8—H8A⋯O2iii	0.98	2.48	3.4000 (11)	156

Symmetry codes: (i) ; (ii) ; (iii) .