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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2797.
Published online 2009 October 17. doi:  10.1107/S1600536809042299
PMCID: PMC2971098

2-(4-Methyl­benzene­sulfonamido)-2-phenyl­acetic acid

Abstract

In the title compound, C15H15NO4S, the dihedral angle between the phenyl and benzene rings is 46.0 (3)° and a weak intra­molecular N—H(...)O inter­action is present. The crystal structure is stabilized by inter­molecular 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 [triangle]); Arshad et al. (2009 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-o2797-scheme1.jpg

Experimental

Crystal data

  • C15H15NO4S
  • M r = 305.35
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2797-efi1.jpg
  • 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 [triangle]) 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 [triangle]), 1550 Freidel pairs
  • Flack parameter: −0.11 (19)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

supplementary crystallographic information

Comment

(R)-alpha-Amino-benzeneacetic is a side chain component of Ampicillin, Cephalexin and Cephaclor. Cephalexin has D-phenylglycyl group as a substituent at the 7-amino position and an unsubstituted methyl group at the 3-position. This is in connection with our previous study on synthesis of sulfonamide derivatives with phenyl glycine (Arshad et al., 2009).

In the title molecule (I), (Fig. 1), bond lengths (Allen et al., 1987) and bond angles are in the range of expected values. The planes of the phenyl and benzene rings (C1–C6) and (C9–C14) make a dihedral angle of 46.0 (3) ° with each other.

In the structure, the adjacent molecules are connected by intermolecular O—H···O, N—H···O and C—H···O hydrogen bonds (Table 1). In Fig. 2, the packing and hydrogen bonding of (I) are shown viewed down a axis.

Experimental

Phenyl glycine (1.0 g, 6.6 mmol) was dissolved in 20 ml distilled in a round bottom flask (100 ml). 1M Na2CO3 solution was used to maintain pH at 8–9. Para-toluene sulfonyl chloride (1.26 g, 6.6 mmol) was added to the solution, and stirred at room temperature until the para-toluene sulfonylchloride was consumed. On completion of the reaction, while vigorous stirring pH was adjusted 1–2, using 1 M HCl. The precipitate formed in this way was filtered off, washed with distilled water, dried and recrystalized in methanol and ethyl acetate (50:50 v/v) to yield light brown prisms of (I).

Refinement

The NH H atom was localized from the difference-Fourier map and its coordinates were refined freely. The isotropic temperature parameters of the H atom were calculated as 1.2Ueq of the parent atom. H atoms were located geometrically and treated as riding with C—H = 0.98 Å (methine), C—H = 0.96 Å (methyl), C—H = 0.93 Å (aromatic) and O—H = 0.82 Å (hydroxyl) with Uiso(H) = 1.2 or 1.5Ueq(C, O).

Figures

Fig. 1.
An ORTEP-3 view of the title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
Fig. 2.
The packing and hydrogen bonding of the title compound viewed down a axis. Hydrogen atoms not involved in the showed interactions have been omitted for clarity.

Crystal data

C15H15NO4SF(000) = 640
Mr = 305.35Dx = 1.370 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 533 reflections
a = 5.6592 (12) Åθ = 2.5–15.0°
b = 11.208 (2) ŵ = 0.23 mm1
c = 23.342 (4) ÅT = 296 K
V = 1480.5 (5) Å3Prism, light brown
Z = 40.35 × 0.22 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer3753 independent reflections
Radiation source: sealed tube1502 reflections with I > 2σ(I)
graphiteRint = 0.0000
[var phi] and ω scansθmax = 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 = 0.977k = 0→15
3753 measured reflectionsl = 0→31

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.192w = 1/[σ2(Fo2) + (0.0657P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max < 0.001
3753 reflectionsΔρmax = 0.30 e Å3
195 parametersΔρmin = −0.38 e Å3
0 restraintsAbsolute structure: Flack (1983), 1550 Freidel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.11 (19)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.0144 (3)0.06971 (13)0.90449 (6)0.0506 (5)
O10.6089 (8)−0.1884 (4)0.93717 (17)0.0620 (16)
O20.2309 (8)−0.2174 (4)0.96274 (18)0.0683 (17)
O3−0.2356 (6)0.0816 (4)0.90143 (16)0.0590 (16)
O40.1628 (7)0.1504 (4)0.87441 (17)0.0607 (17)
N10.0702 (7)−0.0631 (4)0.87997 (19)0.0470 (17)
C10.2019 (12)−0.2702 (6)0.8097 (3)0.070 (3)
C20.2455 (14)−0.3397 (7)0.7628 (3)0.085 (3)
C30.4491 (12)−0.3245 (6)0.7318 (3)0.073 (3)
C40.6069 (13)−0.2379 (6)0.7467 (3)0.072 (3)
C50.5634 (9)−0.1673 (6)0.7937 (3)0.061 (3)
C60.3604 (10)−0.1822 (5)0.8253 (2)0.0463 (19)
C70.3143 (9)−0.1052 (5)0.8779 (2)0.0470 (19)
C80.3763 (11)−0.1745 (5)0.9306 (2)0.050 (2)
C90.0950 (9)0.0722 (5)0.9766 (2)0.0490 (19)
C10−0.0428 (11)0.0200 (5)1.0177 (3)0.062 (2)
C110.0257 (12)0.0163 (6)1.0734 (3)0.070 (3)
C120.2384 (12)0.0650 (6)1.0907 (3)0.067 (2)
C130.3774 (11)0.1171 (6)1.0498 (3)0.065 (3)
C140.3091 (10)0.1222 (5)0.9926 (3)0.057 (2)
C150.3157 (14)0.0600 (8)1.1524 (3)0.099 (3)
H10.06550−0.282200.831100.0840*
HO10.63490−0.226200.966600.0930*
H20.13660−0.397500.751800.1010*
HN1−0.020 (9)−0.116 (5)0.894 (2)0.0560*
H30.47970−0.373400.700400.0880*
H40.74340−0.226700.725200.0870*
H50.67200−0.109000.804200.0730*
H70.41830−0.035400.876000.0560*
H10−0.18660−0.013801.007200.0740*
H11−0.07210−0.019501.100400.0840*
H130.521600.150101.060500.0780*
H140.405700.158600.965500.0690*
H15A0.480700.040401.154200.1490*
H15B0.226000.000201.172200.1490*
H15C0.289700.136201.170100.1490*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0449 (8)0.0563 (8)0.0505 (8)0.0024 (8)0.0026 (8)0.0009 (8)
O10.051 (2)0.074 (3)0.061 (3)−0.001 (2)−0.012 (2)0.021 (2)
O20.066 (3)0.082 (3)0.057 (3)0.003 (2)0.016 (2)0.017 (2)
O30.034 (2)0.076 (3)0.067 (3)0.0123 (19)−0.0037 (19)−0.002 (2)
O40.059 (3)0.055 (3)0.068 (3)−0.002 (2)0.013 (2)0.012 (2)
N10.040 (3)0.054 (3)0.047 (3)0.003 (2)0.001 (2)−0.002 (2)
C10.070 (4)0.078 (5)0.062 (4)−0.014 (4)0.008 (4)−0.024 (4)
C20.082 (5)0.083 (6)0.089 (5)−0.015 (4)0.001 (4)−0.034 (4)
C30.065 (5)0.095 (6)0.060 (4)0.016 (4)0.001 (3)−0.022 (4)
C40.062 (4)0.096 (6)0.059 (5)0.007 (4)0.011 (4)−0.009 (4)
C50.044 (4)0.085 (5)0.053 (4)0.002 (3)0.003 (3)−0.009 (3)
C60.048 (3)0.052 (4)0.039 (3)0.003 (3)0.000 (3)0.000 (3)
C70.038 (3)0.057 (4)0.046 (3)−0.004 (2)−0.002 (2)0.001 (3)
C80.053 (4)0.057 (4)0.040 (3)−0.008 (3)0.002 (3)−0.003 (3)
C90.038 (3)0.056 (3)0.053 (4)0.004 (3)0.004 (3)−0.007 (3)
C100.055 (4)0.069 (4)0.062 (4)−0.008 (3)0.004 (3)−0.005 (3)
C110.075 (5)0.084 (5)0.052 (4)−0.003 (4)0.005 (4)0.000 (3)
C120.071 (4)0.073 (4)0.056 (4)0.010 (4)−0.006 (4)−0.010 (4)
C130.053 (4)0.069 (4)0.072 (5)−0.003 (3)−0.004 (4)−0.014 (4)
C140.050 (4)0.062 (4)0.060 (4)0.000 (3)0.003 (3)−0.007 (3)
C150.108 (6)0.126 (7)0.064 (5)0.017 (6)−0.017 (4)−0.019 (5)

Geometric parameters (Å, °)

S1—O31.423 (4)C10—C111.357 (10)
S1—O41.420 (4)C11—C121.382 (10)
S1—N11.626 (5)C12—C131.368 (10)
S1—C91.744 (5)C12—C151.506 (10)
O1—C81.334 (8)C13—C141.391 (10)
O2—C81.213 (7)C1—H10.9300
O1—HO10.8200C2—H20.9300
N1—C71.461 (7)C3—H30.9300
N1—HN10.85 (5)C4—H40.9300
C1—C61.382 (9)C5—H50.9300
C1—C21.366 (10)C7—H70.9800
C2—C31.371 (10)C10—H100.9300
C3—C41.364 (10)C11—H110.9300
C4—C51.375 (10)C13—H130.9300
C5—C61.375 (8)C14—H140.9300
C6—C71.523 (7)C15—H15A0.9600
C7—C81.497 (7)C15—H15B0.9600
C9—C141.386 (8)C15—H15C0.9600
C9—C101.368 (8)
O3—S1—O4120.2 (3)C13—C12—C15121.1 (6)
O3—S1—N1105.1 (2)C12—C13—C14121.8 (6)
O3—S1—C9107.9 (2)C9—C14—C13119.0 (6)
O4—S1—N1107.1 (2)C2—C1—H1120.00
O4—S1—C9108.2 (3)C6—C1—H1120.00
N1—S1—C9107.7 (3)C1—C2—H2120.00
C8—O1—HO1109.00C3—C2—H2120.00
S1—N1—C7119.4 (3)C2—C3—H3120.00
S1—N1—HN1113 (4)C4—C3—H3120.00
C7—N1—HN1111 (4)C3—C4—H4120.00
C2—C1—C6120.1 (6)C5—C4—H4120.00
C1—C2—C3120.3 (7)C4—C5—H5120.00
C2—C3—C4120.3 (7)C6—C5—H5120.00
C3—C4—C5119.7 (6)N1—C7—H7108.00
C4—C5—C6120.5 (6)C6—C7—H7108.00
C1—C6—C5119.2 (5)C8—C7—H7108.00
C1—C6—C7120.4 (5)C9—C10—H10119.00
C5—C6—C7120.4 (5)C11—C10—H10119.00
N1—C7—C6111.8 (4)C10—C11—H11120.00
C6—C7—C8109.2 (4)C12—C11—H11119.00
N1—C7—C8111.2 (4)C12—C13—H13119.00
O2—C8—C7123.7 (5)C14—C13—H13119.00
O1—C8—C7112.7 (5)C9—C14—H14121.00
O1—C8—O2123.5 (5)C13—C14—H14120.00
S1—C9—C10121.4 (4)C12—C15—H15A109.00
S1—C9—C14119.7 (4)C12—C15—H15B109.00
C10—C9—C14118.8 (5)C12—C15—H15C110.00
C9—C10—C11121.5 (6)H15A—C15—H15B109.00
C10—C11—C12121.1 (6)H15A—C15—H15C109.00
C11—C12—C15121.2 (6)H15B—C15—H15C109.00
C11—C12—C13117.8 (6)
O3—S1—N1—C7−179.2 (4)C1—C6—C7—N1−45.4 (7)
O4—S1—N1—C751.8 (4)C1—C6—C7—C878.1 (7)
C9—S1—N1—C7−64.3 (4)C5—C6—C7—N1136.5 (5)
O3—S1—C9—C1036.7 (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—C10168.2 (5)N1—C7—C8—O218.5 (7)
O4—S1—C9—C14−15.4 (5)C6—C7—C8—O172.0 (6)
N1—S1—C9—C10−76.3 (5)C6—C7—C8—O2−105.3 (6)
N1—S1—C9—C14100.1 (5)S1—C9—C10—C11176.5 (5)
S1—N1—C7—C6−143.9 (4)C14—C9—C10—C110.0 (9)
S1—N1—C7—C893.8 (5)S1—C9—C14—C13−176.2 (5)
C6—C1—C2—C31.6 (11)C10—C9—C14—C130.4 (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—C130.0 (10)
C1—C2—C3—C4−1.6 (11)C10—C11—C12—C15−179.4 (7)
C2—C3—C4—C51.3 (11)C11—C12—C13—C140.3 (10)
C3—C4—C5—C6−0.9 (10)C15—C12—C13—C14179.8 (6)
C4—C5—C6—C10.9 (9)C12—C13—C14—C9−0.5 (9)
C4—C5—C6—C7179.1 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—HO1···O2i0.821.852.655 (6)168
N1—HN1···O1ii0.85 (5)2.47 (5)3.251 (6)154 (5)
N1—HN1···O20.85 (5)2.43 (5)2.748 (6)103 (4)
C7—H7···O3iii0.982.433.343 (7)155

Symmetry codes: (i) x+1/2, −y−1/2, −z+2; (ii) x−1, y, z; (iii) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5142).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Arshad, M. N., Tahir, M. N., Khan, I. U., Shafiq, M. & Ahmad, S. (2009). Acta Cryst. E65, o940. [PMC free article] [PubMed]
  • Asiri, A. M., Akkurt, M., Khan, S. A., Arshad, M. N., Khan, I. U. & Sharif, H. M. A. (2009). Acta Cryst. E65, o1246–o1247. [PMC free article] [PubMed]
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst.28, 53–56.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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