(2R)-2-Benzene-sulfonamido-2-phenyl-ethanoic acid.

In the title compound, C(14)H(13)NO(4)S, the dihedral angle between the aromatic ring planes is 45.52 (18)°. In the crystal structure, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds lead to chains of mol-ecules propagating in [100] in which the the ring motifs R(2) (1)(8), R(2) (2)(8) and R(3) (3)(11) are apparent. These polymeric chains are linked through C-H⋯O inter-actions.

Related literature

For related structures, see: Chaudhuri (1984 ▶); Shan & Huang (1999 ▶). For background, see: Arshad et al. (2008 ▶); Cama et al. (2003 ▶); Dankwardt et al. (2002 ▶); Zhi-jian et al. (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H13NO4S

M = 291.31

Orthorhombic,

a = 5.6022 (5) Å

b = 12.5026 (9) Å

c = 19.7886 (15) Å

V = 1386.03 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.22 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.944, T max = 0.966

8476 measured reflections

2818 independent reflections

1679 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.091

S = 1.01

2818 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 1092 Friedal Pairs

Flack parameter: 0.02 (10)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011611/hb2938sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011611/hb2938Isup2.hkl

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

C14H13NO4S	F(000) = 608
Mr = 291.31	Dx = 1.396 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2818 reflections
a = 5.6022 (5) Å	θ = 2.6–26.7°
b = 12.5026 (9) Å	µ = 0.25 mm−1
c = 19.7886 (15) Å	T = 296 K
V = 1386.03 (19) Å3	Prism, colorless
Z = 4	0.22 × 0.18 × 0.15 mm

Bruker Kappa APEXII CCD diffractometer	2818 independent reflections
Radiation source: fine-focus sealed tube	1679 reflections with I > 2σ(I)
graphite	Rint = 0.050
Detector resolution: 7.80 pixels mm-1	θmax = 26.7°, θmin = 2.6°
ω scans	h = −7→3
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.944, Tmax = 0.966	l = −25→25
8476 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)] = 0.051	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0304P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2818 reflections	Δρmax = 0.23 e Å−3
182 parameters	Δρmin = −0.28 e Å−3
0 restraints	Absolute structure: Flack (1983), 1092 Friedal Pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (10)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.8906 (2)	0.51683 (6)	0.15187 (4)	0.0387 (3)
O1	1.1438 (4)	0.50754 (15)	0.15986 (10)	0.0489 (9)
O2	0.7303 (5)	0.44742 (17)	0.18723 (11)	0.0554 (9)
O3	0.2940 (5)	0.62039 (15)	0.01637 (12)	0.0456 (10)
O4	0.6710 (5)	0.68015 (15)	0.01169 (12)	0.0496 (9)
N1	0.8409 (5)	0.49873 (16)	0.07161 (11)	0.0338 (9)
C1	0.8088 (7)	0.6505 (2)	0.17079 (15)	0.0363 (13)
C2	0.5942 (8)	0.6698 (3)	0.20125 (16)	0.0533 (14)
C3	0.5343 (9)	0.7746 (4)	0.21780 (18)	0.0723 (19)
C4	0.6886 (11)	0.8565 (3)	0.2012 (2)	0.075 (2)
C5	0.8993 (9)	0.8359 (3)	0.16954 (19)	0.0640 (18)
C6	0.9639 (7)	0.7318 (2)	0.15472 (16)	0.0521 (14)
C7	0.6001 (7)	0.49830 (19)	0.04431 (13)	0.0316 (12)
C8	0.5281 (8)	0.6104 (2)	0.02287 (14)	0.0340 (13)
C9	0.5829 (7)	0.4265 (2)	−0.01808 (14)	0.0318 (13)
C10	0.3966 (8)	0.3565 (2)	−0.02540 (17)	0.0507 (13)
C11	0.3774 (10)	0.2936 (3)	−0.0832 (2)	0.0690 (18)
C12	0.5456 (10)	0.3020 (3)	−0.1324 (2)	0.072 (2)
C13	0.7293 (9)	0.3721 (3)	−0.1256 (2)	0.080 (2)
C14	0.7496 (7)	0.4351 (3)	−0.06873 (18)	0.0583 (16)
H1	0.95974	0.48921	0.04478	0.0406*
H2	0.49001	0.61383	0.21076	0.0640*
H3	0.39147	0.78931	0.23985	0.0865*
H3O	0.26138	0.68249	0.00676	0.0547*
H4	0.64818	0.92669	0.21182	0.0899*
H5	1.00004	0.89197	0.15781	0.0768*
H6	1.10972	0.71706	0.13426	0.0624*
H7	0.48902	0.47247	0.07892	0.0379*
H10	0.28216	0.35094	0.00847	0.0608*
H11	0.25062	0.24614	−0.08804	0.0827*
H12	0.53489	0.25964	−0.17091	0.0872*
H13	0.84273	0.37763	−0.15968	0.0956*
H14	0.87550	0.48313	−0.06466	0.0702*

	U11	U22	U33	U12	U13	U23
S1	0.0371 (7)	0.0395 (4)	0.0395 (4)	0.0025 (5)	−0.0015 (5)	0.0072 (4)
O1	0.0308 (18)	0.0569 (13)	0.0590 (14)	0.0051 (14)	−0.0105 (13)	0.0060 (12)
O2	0.055 (2)	0.0573 (14)	0.0538 (14)	−0.0093 (13)	0.0066 (13)	0.0230 (11)
O3	0.037 (2)	0.0322 (13)	0.0677 (16)	0.0072 (13)	0.0039 (16)	0.0136 (12)
O4	0.048 (2)	0.0318 (11)	0.0690 (16)	−0.0128 (14)	−0.0048 (14)	0.0143 (10)
N1	0.030 (2)	0.0351 (13)	0.0364 (13)	0.0025 (15)	0.0059 (13)	−0.0056 (11)
C1	0.031 (3)	0.0481 (19)	0.0297 (18)	−0.0040 (18)	0.0001 (17)	−0.0046 (14)
C2	0.045 (3)	0.067 (2)	0.048 (2)	0.001 (3)	0.000 (2)	−0.0200 (17)
C3	0.049 (4)	0.096 (3)	0.072 (3)	0.016 (3)	−0.006 (2)	−0.039 (3)
C4	0.085 (5)	0.059 (3)	0.082 (3)	0.015 (3)	−0.011 (3)	−0.033 (2)
C5	0.070 (4)	0.046 (2)	0.076 (3)	−0.010 (2)	−0.004 (3)	−0.0124 (19)
C6	0.057 (3)	0.0494 (19)	0.050 (2)	0.001 (2)	0.009 (2)	−0.0060 (19)
C7	0.032 (3)	0.0251 (15)	0.0378 (16)	0.0002 (19)	0.0039 (17)	0.0037 (12)
C8	0.041 (3)	0.0298 (18)	0.0311 (17)	0.002 (2)	0.003 (2)	−0.0001 (14)
C9	0.030 (3)	0.0242 (14)	0.0412 (18)	0.0008 (17)	0.0001 (18)	0.0012 (13)
C10	0.057 (3)	0.0360 (17)	0.059 (2)	−0.006 (2)	0.003 (2)	−0.0045 (16)
C11	0.082 (4)	0.045 (2)	0.080 (3)	−0.014 (2)	−0.017 (3)	−0.012 (2)
C12	0.093 (5)	0.062 (3)	0.062 (3)	−0.005 (3)	−0.011 (3)	−0.027 (2)
C13	0.078 (5)	0.103 (3)	0.059 (3)	−0.017 (3)	0.020 (3)	−0.029 (2)
C14	0.059 (4)	0.068 (2)	0.048 (2)	−0.022 (2)	0.013 (2)	−0.017 (2)

S1—O1	1.432 (3)	C9—C14	1.374 (5)
S1—O2	1.432 (3)	C9—C10	1.370 (5)
S1—N1	1.628 (2)	C10—C11	1.392 (5)
S1—C1	1.773 (3)	C11—C12	1.359 (7)
O3—C8	1.324 (5)	C12—C13	1.358 (7)
O4—C8	1.204 (4)	C13—C14	1.378 (5)
O3—H3O	0.8200	C2—H2	0.9300
N1—C7	1.453 (5)	C3—H3	0.9300
N1—H1	0.8600	C4—H4	0.9300
C1—C2	1.366 (6)	C5—H5	0.9300
C1—C6	1.375 (4)	C6—H6	0.9300
C2—C3	1.392 (6)	C7—H7	0.9800
C3—C4	1.380 (7)	C10—H10	0.9300
C4—C5	1.361 (7)	C11—H11	0.9300
C5—C6	1.382 (5)	C12—H12	0.9300
C7—C8	1.519 (4)	C13—H13	0.9300
C7—C9	1.530 (4)	C14—H14	0.9300
O1—S1—O2	121.22 (14)	C10—C11—C12	119.4 (4)
O1—S1—N1	105.42 (14)	C11—C12—C13	120.3 (4)
O1—S1—C1	108.01 (15)	C12—C13—C14	120.8 (4)
O2—S1—N1	106.58 (14)	C9—C14—C13	119.7 (4)
O2—S1—C1	107.82 (16)	C1—C2—H2	121.00
N1—S1—C1	107.03 (13)	C3—C2—H2	121.00
C8—O3—H3O	109.00	C2—C3—H3	120.00
S1—N1—C7	121.5 (2)	C4—C3—H3	120.00
S1—N1—H1	119.00	C3—C4—H4	120.00
C7—N1—H1	119.00	C5—C4—H4	120.00
C2—C1—C6	121.9 (3)	C4—C5—H5	120.00
S1—C1—C2	119.2 (3)	C6—C5—H5	120.00
S1—C1—C6	119.0 (3)	C1—C6—H6	121.00
C1—C2—C3	118.8 (4)	C5—C6—H6	121.00
C2—C3—C4	119.5 (4)	N1—C7—H7	109.00
C3—C4—C5	120.8 (4)	C8—C7—H7	109.00
C4—C5—C6	120.2 (4)	C9—C7—H7	109.00
C1—C6—C5	118.8 (4)	C9—C10—H10	120.00
C8—C7—C9	107.4 (2)	C11—C10—H10	120.00
N1—C7—C9	111.2 (3)	C10—C11—H11	120.00
N1—C7—C8	110.3 (3)	C12—C11—H11	120.00
O3—C8—O4	124.9 (3)	C11—C12—H12	120.00
O3—C8—C7	112.2 (3)	C13—C12—H12	120.00
O4—C8—C7	122.9 (4)	C12—C13—H13	120.00
C7—C9—C10	120.6 (3)	C14—C13—H13	120.00
C7—C9—C14	120.0 (3)	C9—C14—H14	120.00
C10—C9—C14	119.4 (3)	C13—C14—H14	120.00
C9—C10—C11	120.4 (4)
O1—S1—N1—C7	177.57 (18)	C4—C5—C6—C1	1.8 (6)
O2—S1—N1—C7	47.6 (2)	N1—C7—C8—O3	−161.7 (2)
C1—S1—N1—C7	−67.6 (2)	N1—C7—C8—O4	20.1 (4)
O1—S1—C1—C2	−145.8 (3)	C9—C7—C8—O3	77.0 (3)
O1—S1—C1—C6	33.9 (3)	C9—C7—C8—O4	−101.2 (4)
O2—S1—C1—C2	−13.2 (3)	N1—C7—C9—C10	134.8 (3)
O2—S1—C1—C6	166.5 (3)	N1—C7—C9—C14	−48.0 (4)
N1—S1—C1—C2	101.2 (3)	C8—C7—C9—C10	−104.5 (3)
N1—S1—C1—C6	−79.2 (3)	C8—C7—C9—C14	72.7 (4)
S1—N1—C7—C8	90.6 (2)	C7—C9—C10—C11	178.0 (3)
S1—N1—C7—C9	−150.35 (18)	C14—C9—C10—C11	0.8 (5)
S1—C1—C2—C3	178.1 (3)	C7—C9—C14—C13	−178.3 (3)
C6—C1—C2—C3	−1.5 (5)	C10—C9—C14—C13	−1.0 (5)
S1—C1—C6—C5	180.0 (3)	C9—C10—C11—C12	0.1 (6)
C2—C1—C6—C5	−0.4 (5)	C10—C11—C12—C13	−0.8 (7)
C1—C2—C3—C4	2.1 (6)	C11—C12—C13—C14	0.5 (7)
C2—C3—C4—C5	−0.7 (6)	C12—C13—C14—C9	0.4 (6)
C3—C4—C5—C6	−1.3 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.86	2.55	3.155 (4)	128
O3—H3O···O4ii	0.82	1.83	2.646 (3)	176
C2—H2···O1iii	0.93	2.56	3.340 (5)	142
C3—H3···O2iv	0.93	2.54	3.225 (5)	131
C7—H7···O1iii	0.98	2.55	3.432 (4)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.86	2.55	3.155 (4)	128
O3—H3O⋯O4ii	0.82	1.83	2.646 (3)	176
C2—H2⋯O1iii	0.93	2.56	3.340 (5)	142
C3—H3⋯O2iv	0.93	2.54	3.225 (5)	131
C7—H7⋯O1iii	0.98	2.55	3.432 (4)	150

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