Crystal structure of 2-benzene-sulfon-amido-3-hy-droxy-propanoic acid.

In the title compound, C9H11NO5S, the O=S=O plane of the sulfonyl group is twisted at a dihedral angle of 52.54 (16)° with respect to the benzene ring. The dihedral angle between the carb-oxy-lic acid group and the benzene ring is 49.91 (16)°. In the crystal, C-H⋯O, N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into (001) sheets.

Related literature

For related structures, see: Aguilar-Castro et al. (2004 ▸); Arshad et al. (2009 ▸, 2012 ▸); Zolotarev et al. (2014 ▸).

Experimental

Crystal data

C9H11NO5S

M = 245.25

Orthorhombic,

a = 5.0464 (4) Å

b = 9.9752 (8) Å

c = 21.4701 (17) Å

V = 1080.78 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.40 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▸) T min = 0.890, T max = 0.950

5013 measured reflections

2354 independent reflections

1978 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.093

S = 1.03

2354 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack x determined using 919 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)

Absolute structure parameter: 0.05 (5)

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT (Bruker, 2007 ▸); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015020149/hb7530sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015020149/hb7530Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015020149/hb7530Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015020149/hb7530fig1.tif

View of the asymmetric unit of title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

PLATON . DOI: 10.1107/S2056989015020149/hb7530fig2.tif

The partial packing (PLATON; Spek, 2009), which shows that mol­ecules form two dimensional polymeric network.

CCDC reference: 1433189

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H11NO5S	Dx = 1.507 Mg m−3
Mr = 245.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1978 reflections
a = 5.0464 (4) Å	θ = 2.8–27.1°
b = 9.9752 (8) Å	µ = 0.31 mm−1
c = 21.4701 (17) Å	T = 296 K
V = 1080.78 (15) Å3	Needle, colorless
Z = 4	0.40 × 0.20 × 0.18 mm
F(000) = 512

Bruker Kappa APEXII CCD diffractometer	2354 independent reflections
Radiation source: fine-focus sealed tube	1978 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 7.80 pixels mm-1	θmax = 27.1°, θmin = 2.8°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→12
Tmin = 0.890, Tmax = 0.950	l = −27→27
5013 measured reflections

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0432P)2 + 0.1053P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2354 reflections	Δρmax = 0.21 e Å−3
149 parameters	Δρmin = −0.28 e Å−3
0 restraints	Absolute structure: Flack x determined using 919 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (5)

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.

	x	y	z	Uiso*/Ueq
S1	0.68841 (17)	0.37500 (8)	0.12794 (3)	0.0362 (2)
O1	0.7864 (6)	0.8154 (3)	0.20233 (14)	0.0624 (8)
H1	0.871 (11)	0.885 (5)	0.194 (2)	0.094*
O2	1.1199 (6)	0.6949 (3)	0.16402 (14)	0.0651 (8)
O3	0.9705 (7)	0.5474 (2)	0.30216 (11)	0.0583 (8)
H3	1.0059	0.6065	0.3274	0.087*
O4	0.4135 (5)	0.3816 (3)	0.14371 (11)	0.0504 (6)
O5	0.8178 (6)	0.2474 (2)	0.12476 (11)	0.0502 (6)
N1	0.8462 (6)	0.4600 (2)	0.17945 (11)	0.0368 (6)
H1A	0.9985	0.4323	0.1920	0.044*
C1	0.9047 (8)	0.7029 (3)	0.18768 (14)	0.0406 (8)
C2	0.7369 (7)	0.5833 (3)	0.20543 (14)	0.0384 (8)
H2	0.5583	0.5962	0.1886	0.046*
C3	0.7171 (9)	0.5712 (4)	0.27649 (16)	0.0530 (10)
H3A	0.6444	0.6533	0.2936	0.064*
H3B	0.5990	0.4981	0.2873	0.064*
C4	0.7318 (7)	0.4526 (3)	0.05482 (14)	0.0365 (8)
C5	0.9275 (9)	0.4077 (4)	0.01556 (16)	0.0542 (10)
H5	1.0338	0.3355	0.0269	0.065*
C6	0.9645 (11)	0.4717 (4)	−0.04132 (17)	0.0653 (12)
H6	1.0988	0.4436	−0.0679	0.078*
C7	0.8028 (10)	0.5765 (4)	−0.05829 (16)	0.0609 (11)
H7	0.8250	0.6180	−0.0967	0.073*
C8	0.6103 (9)	0.6193 (4)	−0.01864 (17)	0.0618 (12)
H8	0.5028	0.6909	−0.0301	0.074*
C9	0.5718 (9)	0.5581 (4)	0.03840 (17)	0.0512 (9)
H9	0.4395	0.5879	0.0652	0.061*

	U11	U22	U33	U12	U13	U23
S1	0.0337 (4)	0.0291 (3)	0.0459 (4)	−0.0024 (4)	−0.0051 (4)	0.0017 (3)
O1	0.061 (2)	0.0327 (13)	0.0933 (19)	0.0046 (14)	0.0105 (17)	−0.0028 (13)
O2	0.054 (2)	0.0441 (14)	0.097 (2)	0.0024 (14)	0.0283 (17)	0.0134 (14)
O3	0.089 (2)	0.0342 (13)	0.0514 (14)	0.0014 (15)	−0.0182 (15)	−0.0063 (10)
O4	0.0350 (13)	0.0529 (14)	0.0634 (14)	−0.0087 (13)	−0.0019 (13)	0.0046 (12)
O5	0.0590 (17)	0.0282 (11)	0.0635 (14)	0.0039 (11)	−0.0118 (16)	0.0015 (10)
N1	0.0325 (16)	0.0352 (14)	0.0428 (12)	0.0059 (13)	−0.0089 (14)	−0.0030 (11)
C1	0.042 (2)	0.0349 (17)	0.0444 (17)	0.0068 (17)	−0.0013 (18)	0.0026 (14)
C2	0.0300 (19)	0.0357 (16)	0.0496 (16)	0.0040 (14)	−0.0014 (16)	−0.0043 (13)
C3	0.059 (3)	0.0427 (19)	0.0569 (19)	−0.005 (2)	0.025 (2)	−0.0085 (15)
C4	0.036 (2)	0.0331 (15)	0.0405 (14)	−0.0015 (16)	−0.0064 (16)	−0.0051 (12)
C5	0.059 (3)	0.051 (2)	0.0528 (19)	0.018 (2)	0.001 (2)	−0.0045 (16)
C6	0.081 (3)	0.069 (3)	0.0457 (19)	0.011 (3)	0.014 (2)	−0.011 (2)
C7	0.080 (3)	0.062 (2)	0.0400 (16)	0.000 (3)	−0.006 (2)	0.0020 (16)
C8	0.071 (3)	0.057 (2)	0.058 (2)	0.014 (2)	−0.011 (2)	0.0106 (19)
C9	0.048 (2)	0.050 (2)	0.0560 (19)	0.0159 (19)	0.003 (2)	0.0046 (17)

S1—O4	1.429 (3)	C3—H3A	0.9700
S1—O5	1.432 (2)	C3—H3B	0.9700
S1—N1	1.605 (3)	C4—C9	1.373 (5)
S1—C4	1.764 (3)	C4—C5	1.374 (5)
O1—C1	1.310 (4)	C5—C6	1.391 (5)
O1—H1	0.84 (5)	C5—H5	0.9300
O2—C1	1.201 (4)	C6—C7	1.375 (6)
O3—C3	1.413 (5)	C6—H6	0.9300
O3—H3	0.8200	C7—C8	1.360 (6)
N1—C2	1.458 (4)	C7—H7	0.9300
N1—H1A	0.8600	C8—C9	1.382 (5)
C1—C2	1.512 (5)	C8—H8	0.9300
C2—C3	1.534 (5)	C9—H9	0.9300
C2—H2	0.9800
O4—S1—O5	119.67 (16)	C2—C3—H3A	109.7
O4—S1—N1	107.09 (15)	O3—C3—H3B	109.7
O5—S1—N1	106.03 (14)	C2—C3—H3B	109.7
O4—S1—C4	108.12 (15)	H3A—C3—H3B	108.2
O5—S1—C4	106.92 (15)	C9—C4—C5	121.0 (3)
N1—S1—C4	108.64 (14)	C9—C4—S1	119.5 (3)
C1—O1—H1	115 (4)	C5—C4—S1	119.5 (3)
C3—O3—H3	109.5	C4—C5—C6	119.1 (4)
C2—N1—S1	121.4 (2)	C4—C5—H5	120.5
C2—N1—H1A	119.3	C6—C5—H5	120.5
S1—N1—H1A	119.3	C7—C6—C5	120.1 (4)
O2—C1—O1	124.8 (4)	C7—C6—H6	119.9
O2—C1—C2	124.1 (3)	C5—C6—H6	119.9
O1—C1—C2	111.1 (3)	C8—C7—C6	119.7 (4)
N1—C2—C1	110.9 (3)	C8—C7—H7	120.1
N1—C2—C3	109.8 (3)	C6—C7—H7	120.1
C1—C2—C3	110.4 (3)	C7—C8—C9	121.1 (4)
N1—C2—H2	108.5	C7—C8—H8	119.4
C1—C2—H2	108.5	C9—C8—H8	119.4
C3—C2—H2	108.5	C4—C9—C8	118.9 (4)
O3—C3—C2	110.0 (3)	C4—C9—H9	120.6
O3—C3—H3A	109.7	C8—C9—H9	120.6
O4—S1—N1—C2	−37.2 (3)	N1—S1—C4—C9	−83.5 (3)
O5—S1—N1—C2	−166.0 (2)	O4—S1—C4—C5	−148.5 (3)
C4—S1—N1—C2	79.4 (3)	O5—S1—C4—C5	−18.4 (3)
S1—N1—C2—C1	−114.8 (3)	N1—S1—C4—C5	95.6 (3)
S1—N1—C2—C3	122.8 (3)	C9—C4—C5—C6	0.7 (6)
O2—C1—C2—N1	−11.0 (5)	S1—C4—C5—C6	−178.4 (3)
O1—C1—C2—N1	170.0 (3)	C4—C5—C6—C7	−1.4 (6)
O2—C1—C2—C3	111.1 (4)	C5—C6—C7—C8	1.4 (7)
O1—C1—C2—C3	−68.0 (4)	C6—C7—C8—C9	−0.8 (7)
N1—C2—C3—O3	59.3 (4)	C5—C4—C9—C8	−0.1 (6)
C1—C2—C3—O3	−63.3 (4)	S1—C4—C9—C8	179.1 (3)
O4—S1—C4—C9	32.4 (3)	C7—C8—C9—C4	0.1 (7)
O5—S1—C4—C9	162.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.84 (5)	1.81 (5)	2.621 (4)	164 (5)
O3—H3···O5i	0.82	1.96	2.754 (3)	164
N1—H1A···O4ii	0.86	2.39	3.066 (4)	136
C2—H2···O2iii	0.98	2.48	3.425 (5)	162
C6—H6···O5iv	0.93	2.52	3.342 (5)	148
C7—H7···O2v	0.93	2.58	3.347 (5)	141

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1O3i	0.84(5)	1.81(5)	2.621(4)	164(5)
O3H3O5i	0.82	1.96	2.754(3)	164
N1H1AO4ii	0.86	2.39	3.066(4)	136
C2H2O2iii	0.98	2.48	3.425(5)	162
C6H6O5iv	0.93	2.52	3.342(5)	148
C7H7O2v	0.93	2.58	3.347(5)	141

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