2-(4-Methyl-benzene-sulfonamido)-2-phenyl-acetic acid.

In the title compound, C(15)H(15)NO(4)S, the dihedral angle between the phenyl and benzene rings is 46.0 (3)° and a weak intra-molecular N-H⋯O inter-action is present. The crystal structure is stabilized by inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For previous studies on the synthesis of sulfonamide derivatives with phenyl glycine, see: Asiri et al. (2009 ▶); Arshad et al. (2009 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H15NO4S

M = 305.35

Orthorhombic,

a = 5.6592 (12) Å

b = 11.208 (2) Å

c = 23.342 (4) Å

V = 1480.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.35 × 0.22 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: refined from ΔF (XABS2; Parkin et al., 1995 ▶) T min = 0.923, T max = 0.977

3753 measured reflections

3753 independent reflections

1502 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.192

S = 0.94

3753 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.38 e Å−3

Absolute structure: Flack (1983 ▶), 1550 Freidel pairs

Flack parameter: −0.11 (19)

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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809042299/hb5142sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042299/hb5142Isup2.hkl

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

C15H15NO4S	F(000) = 640
Mr = 305.35	Dx = 1.370 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 533 reflections
a = 5.6592 (12) Å	θ = 2.5–15.0°
b = 11.208 (2) Å	µ = 0.23 mm−1
c = 23.342 (4) Å	T = 296 K
V = 1480.5 (5) Å3	Prism, light brown
Z = 4	0.35 × 0.22 × 0.10 mm

Bruker Kappa APEXII CCD diffractometer	3753 independent reflections
Radiation source: sealed tube	1502 reflections with I > 2σ(I)
graphite	Rint = 0.0000
φ and ω scans	θmax = 28.6°, θmin = 1.7°
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	h = −7→7
Tmin = 0.923, Tmax = 0.977	k = 0→15
3753 measured reflections	l = 0→31

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)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.192	w = 1/[σ2(Fo2) + (0.0657P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max < 0.001
3753 reflections	Δρmax = 0.30 e Å−3
195 parameters	Δρmin = −0.38 e Å−3
0 restraints	Absolute structure: Flack (1983), 1550 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.11 (19)

Experimental. Absorption correction: XABS2; Parkin et al. (1995), linear fit to sin(theta)/lambda - 12 parameters

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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.0144 (3)	0.06971 (13)	0.90449 (6)	0.0506 (5)
O1	0.6089 (8)	−0.1884 (4)	0.93717 (17)	0.0620 (16)
O2	0.2309 (8)	−0.2174 (4)	0.96274 (18)	0.0683 (17)
O3	−0.2356 (6)	0.0816 (4)	0.90143 (16)	0.0590 (16)
O4	0.1628 (7)	0.1504 (4)	0.87441 (17)	0.0607 (17)
N1	0.0702 (7)	−0.0631 (4)	0.87997 (19)	0.0470 (17)
C1	0.2019 (12)	−0.2702 (6)	0.8097 (3)	0.070 (3)
C2	0.2455 (14)	−0.3397 (7)	0.7628 (3)	0.085 (3)
C3	0.4491 (12)	−0.3245 (6)	0.7318 (3)	0.073 (3)
C4	0.6069 (13)	−0.2379 (6)	0.7467 (3)	0.072 (3)
C5	0.5634 (9)	−0.1673 (6)	0.7937 (3)	0.061 (3)
C6	0.3604 (10)	−0.1822 (5)	0.8253 (2)	0.0463 (19)
C7	0.3143 (9)	−0.1052 (5)	0.8779 (2)	0.0470 (19)
C8	0.3763 (11)	−0.1745 (5)	0.9306 (2)	0.050 (2)
C9	0.0950 (9)	0.0722 (5)	0.9766 (2)	0.0490 (19)
C10	−0.0428 (11)	0.0200 (5)	1.0177 (3)	0.062 (2)
C11	0.0257 (12)	0.0163 (6)	1.0734 (3)	0.070 (3)
C12	0.2384 (12)	0.0650 (6)	1.0907 (3)	0.067 (2)
C13	0.3774 (11)	0.1171 (6)	1.0498 (3)	0.065 (3)
C14	0.3091 (10)	0.1222 (5)	0.9926 (3)	0.057 (2)
C15	0.3157 (14)	0.0600 (8)	1.1524 (3)	0.099 (3)
H1	0.06550	−0.28220	0.83110	0.0840*
HO1	0.63490	−0.22620	0.96660	0.0930*
H2	0.13660	−0.39750	0.75180	0.1010*
HN1	−0.020 (9)	−0.116 (5)	0.894 (2)	0.0560*
H3	0.47970	−0.37340	0.70040	0.0880*
H4	0.74340	−0.22670	0.72520	0.0870*
H5	0.67200	−0.10900	0.80420	0.0730*
H7	0.41830	−0.03540	0.87600	0.0560*
H10	−0.18660	−0.01380	1.00720	0.0740*
H11	−0.07210	−0.01950	1.10040	0.0840*
H13	0.52160	0.15010	1.06050	0.0780*
H14	0.40570	0.15860	0.96550	0.0690*
H15A	0.48070	0.04040	1.15420	0.1490*
H15B	0.22600	0.00020	1.17220	0.1490*
H15C	0.28970	0.13620	1.17010	0.1490*

	U11	U22	U33	U12	U13	U23
S1	0.0449 (8)	0.0563 (8)	0.0505 (8)	0.0024 (8)	0.0026 (8)	0.0009 (8)
O1	0.051 (2)	0.074 (3)	0.061 (3)	−0.001 (2)	−0.012 (2)	0.021 (2)
O2	0.066 (3)	0.082 (3)	0.057 (3)	0.003 (2)	0.016 (2)	0.017 (2)
O3	0.034 (2)	0.076 (3)	0.067 (3)	0.0123 (19)	−0.0037 (19)	−0.002 (2)
O4	0.059 (3)	0.055 (3)	0.068 (3)	−0.002 (2)	0.013 (2)	0.012 (2)
N1	0.040 (3)	0.054 (3)	0.047 (3)	0.003 (2)	0.001 (2)	−0.002 (2)
C1	0.070 (4)	0.078 (5)	0.062 (4)	−0.014 (4)	0.008 (4)	−0.024 (4)
C2	0.082 (5)	0.083 (6)	0.089 (5)	−0.015 (4)	0.001 (4)	−0.034 (4)
C3	0.065 (5)	0.095 (6)	0.060 (4)	0.016 (4)	0.001 (3)	−0.022 (4)
C4	0.062 (4)	0.096 (6)	0.059 (5)	0.007 (4)	0.011 (4)	−0.009 (4)
C5	0.044 (4)	0.085 (5)	0.053 (4)	0.002 (3)	0.003 (3)	−0.009 (3)
C6	0.048 (3)	0.052 (4)	0.039 (3)	0.003 (3)	0.000 (3)	0.000 (3)
C7	0.038 (3)	0.057 (4)	0.046 (3)	−0.004 (2)	−0.002 (2)	0.001 (3)
C8	0.053 (4)	0.057 (4)	0.040 (3)	−0.008 (3)	0.002 (3)	−0.003 (3)
C9	0.038 (3)	0.056 (3)	0.053 (4)	0.004 (3)	0.004 (3)	−0.007 (3)
C10	0.055 (4)	0.069 (4)	0.062 (4)	−0.008 (3)	0.004 (3)	−0.005 (3)
C11	0.075 (5)	0.084 (5)	0.052 (4)	−0.003 (4)	0.005 (4)	0.000 (3)
C12	0.071 (4)	0.073 (4)	0.056 (4)	0.010 (4)	−0.006 (4)	−0.010 (4)
C13	0.053 (4)	0.069 (4)	0.072 (5)	−0.003 (3)	−0.004 (4)	−0.014 (4)
C14	0.050 (4)	0.062 (4)	0.060 (4)	0.000 (3)	0.003 (3)	−0.007 (3)
C15	0.108 (6)	0.126 (7)	0.064 (5)	0.017 (6)	−0.017 (4)	−0.019 (5)

S1—O3	1.423 (4)	C10—C11	1.357 (10)
S1—O4	1.420 (4)	C11—C12	1.382 (10)
S1—N1	1.626 (5)	C12—C13	1.368 (10)
S1—C9	1.744 (5)	C12—C15	1.506 (10)
O1—C8	1.334 (8)	C13—C14	1.391 (10)
O2—C8	1.213 (7)	C1—H1	0.9300
O1—HO1	0.8200	C2—H2	0.9300
N1—C7	1.461 (7)	C3—H3	0.9300
N1—HN1	0.85 (5)	C4—H4	0.9300
C1—C6	1.382 (9)	C5—H5	0.9300
C1—C2	1.366 (10)	C7—H7	0.9800
C2—C3	1.371 (10)	C10—H10	0.9300
C3—C4	1.364 (10)	C11—H11	0.9300
C4—C5	1.375 (10)	C13—H13	0.9300
C5—C6	1.375 (8)	C14—H14	0.9300
C6—C7	1.523 (7)	C15—H15A	0.9600
C7—C8	1.497 (7)	C15—H15B	0.9600
C9—C14	1.386 (8)	C15—H15C	0.9600
C9—C10	1.368 (8)
O3—S1—O4	120.2 (3)	C13—C12—C15	121.1 (6)
O3—S1—N1	105.1 (2)	C12—C13—C14	121.8 (6)
O3—S1—C9	107.9 (2)	C9—C14—C13	119.0 (6)
O4—S1—N1	107.1 (2)	C2—C1—H1	120.00
O4—S1—C9	108.2 (3)	C6—C1—H1	120.00
N1—S1—C9	107.7 (3)	C1—C2—H2	120.00
C8—O1—HO1	109.00	C3—C2—H2	120.00
S1—N1—C7	119.4 (3)	C2—C3—H3	120.00
S1—N1—HN1	113 (4)	C4—C3—H3	120.00
C7—N1—HN1	111 (4)	C3—C4—H4	120.00
C2—C1—C6	120.1 (6)	C5—C4—H4	120.00
C1—C2—C3	120.3 (7)	C4—C5—H5	120.00
C2—C3—C4	120.3 (7)	C6—C5—H5	120.00
C3—C4—C5	119.7 (6)	N1—C7—H7	108.00
C4—C5—C6	120.5 (6)	C6—C7—H7	108.00
C1—C6—C5	119.2 (5)	C8—C7—H7	108.00
C1—C6—C7	120.4 (5)	C9—C10—H10	119.00
C5—C6—C7	120.4 (5)	C11—C10—H10	119.00
N1—C7—C6	111.8 (4)	C10—C11—H11	120.00
C6—C7—C8	109.2 (4)	C12—C11—H11	119.00
N1—C7—C8	111.2 (4)	C12—C13—H13	119.00
O2—C8—C7	123.7 (5)	C14—C13—H13	119.00
O1—C8—C7	112.7 (5)	C9—C14—H14	121.00
O1—C8—O2	123.5 (5)	C13—C14—H14	120.00
S1—C9—C10	121.4 (4)	C12—C15—H15A	109.00
S1—C9—C14	119.7 (4)	C12—C15—H15B	109.00
C10—C9—C14	118.8 (5)	C12—C15—H15C	110.00
C9—C10—C11	121.5 (6)	H15A—C15—H15B	109.00
C10—C11—C12	121.1 (6)	H15A—C15—H15C	109.00
C11—C12—C15	121.2 (6)	H15B—C15—H15C	109.00
C11—C12—C13	117.8 (6)
O3—S1—N1—C7	−179.2 (4)	C1—C6—C7—N1	−45.4 (7)
O4—S1—N1—C7	51.8 (4)	C1—C6—C7—C8	78.1 (7)
C9—S1—N1—C7	−64.3 (4)	C5—C6—C7—N1	136.5 (5)
O3—S1—C9—C10	36.7 (6)	C5—C6—C7—C8	−100.0 (6)
O3—S1—C9—C14	−146.9 (5)	N1—C7—C8—O1	−164.1 (4)
O4—S1—C9—C10	168.2 (5)	N1—C7—C8—O2	18.5 (7)
O4—S1—C9—C14	−15.4 (5)	C6—C7—C8—O1	72.0 (6)
N1—S1—C9—C10	−76.3 (5)	C6—C7—C8—O2	−105.3 (6)
N1—S1—C9—C14	100.1 (5)	S1—C9—C10—C11	176.5 (5)
S1—N1—C7—C6	−143.9 (4)	C14—C9—C10—C11	0.0 (9)
S1—N1—C7—C8	93.8 (5)	S1—C9—C14—C13	−176.2 (5)
C6—C1—C2—C3	1.6 (11)	C10—C9—C14—C13	0.4 (8)
C2—C1—C6—C5	−1.2 (10)	C9—C10—C11—C12	−0.2 (10)
C2—C1—C6—C7	−179.4 (6)	C10—C11—C12—C13	0.0 (10)
C1—C2—C3—C4	−1.6 (11)	C10—C11—C12—C15	−179.4 (7)
C2—C3—C4—C5	1.3 (11)	C11—C12—C13—C14	0.3 (10)
C3—C4—C5—C6	−0.9 (10)	C15—C12—C13—C14	179.8 (6)
C4—C5—C6—C1	0.9 (9)	C12—C13—C14—C9	−0.5 (9)
C4—C5—C6—C7	179.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—HO1···O2i	0.82	1.85	2.655 (6)	168
N1—HN1···O1ii	0.85 (5)	2.47 (5)	3.251 (6)	154 (5)
N1—HN1···O2	0.85 (5)	2.43 (5)	2.748 (6)	103 (4)
C7—H7···O3iii	0.98	2.43	3.343 (7)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—HO1⋯O2i	0.82	1.85	2.655 (6)	168
N1—HN1⋯O1ii	0.85 (5)	2.47 (5)	3.251 (6)	154 (5)
N1—HN1⋯O2	0.85 (5)	2.43 (5)	2.748 (6)	103 (4)
C7—H7⋯O3iii	0.98	2.43	3.343 (7)	155

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