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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1088.
Published online 2010 April 14. doi:  10.1107/S160053681001322X
PMCID: PMC2979209

N-(4-Hydroxy­phen­yl)benzene­sulfon­amide

Abstract

The title compound, C12H11NO3S, synthesized by the reaction of benzene sulfonyl chloride with para-amino­phenol, is of inter­est as a precursor to biologically active sulfur-containing heterocyclic compounds. The structure is stabilized by N—H(...)O and O—H(...)O hydrogen bonds.

Related literature

For the synthesis of related mol­ecules, see: Zia-ur-Rehman et al. (2006 [triangle], 2009 [triangle]). For a related structure, see: Khan et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1088-scheme1.jpg

Experimental

Crystal data

  • C12H11NO3S
  • M r = 249.28
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1088-efi1.jpg
  • a = 5.1072 (2) Å
  • b = 9.3948 (4) Å
  • c = 24.0903 (10) Å
  • V = 1155.88 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 296 K
  • 0.12 × 0.12 × 0.10 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • 6402 measured reflections
  • 2808 independent reflections
  • 2076 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.146
  • S = 1.02
  • 2808 reflections
  • 155 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.26 e Å−3
  • Absolute structure: Flack (1983 [triangle]), with 1118 Friedel pairs
  • Flack parameter: 0.08 (13)

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: PLATON (Spek, 2009 [triangle]) and Mercury (Macrae et al., 2006 [triangle]); software used to prepare material for publication: PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001322X/bt5239sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001322X/bt5239Isup2.hkl

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

Acknowledgments

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

supplementary crystallographic information

Comment

In the present paper, the structure of N-(4-hydroxyphenyl) benzene sulfonamide (Fig. 1) has been determined as part of a research program involving the synthesis and biological evaluation of sulfur containing heterocyclic compounds (Zia-ur-Rehman et al., 2006, 2009; Khan et al., 2009). Bond lengths and bond angles are almost similar to those in the related molecules (Khan et al., 2009). The molecules are linked through intermolecular N—H···O and O—H···O hydrogen bonds (Fig. 2; Table 1).

Experimental

A mixture of benzene sulfonyl chloride (10.0 mmoles; 1.766 g), para-aminophenol (10.0 mmoles; 1.286 g), aqueous sodium carbonate (10%; 10.0 ml) and water (25 ml) was stirred for half an hour at room temperature followed by evaporation of the solvent. The crude mixture was washed with water and dried. Product obtained was dissolved in methanol and crystallized by slow evaporation of the solvent. Yield 73%.

Refinement

All H atoms were identified in the difference map. Nevertheless, they were fixed in ideal positions and treated as riding on their parent atoms. The following distances were used: Cmethyl—H 0.98 Å, Caromatic—H 0.95Å, O—H 0.84 Å. U(H) was set to 1.2Ueq of the parent atoms or 1.5Ueq for methyl groups.

Figures

Fig. 1.
The molecular structure of the title compound with displacement ellipsoids at the 50% probability level.
Fig. 2.
Perspective view of the three-dimensional crystal packing showing hydrogen-bonded interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C12H11NO3SF(000) = 520
Mr = 249.28Dx = 1.432 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6462 reflections
a = 5.1072 (2) Åθ = 2.5–27.1°
b = 9.3948 (4) ŵ = 0.28 mm1
c = 24.0903 (10) ÅT = 296 K
V = 1155.88 (8) Å3Needle, colourless
Z = 40.12 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer2076 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
graphiteθmax = 28.3°, θmin = 1.7°
[var phi] and ω scansh = −4→6
6402 measured reflectionsk = −8→12
2808 independent reflectionsl = −32→32

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.146w = 1/[σ2(Fo2) + (0.0829P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2808 reflectionsΔρmax = 0.26 e Å3
155 parametersΔρmin = −0.26 e Å3
0 restraintsAbsolute structure: Flack (1983), 1118 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.08 (13)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

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

xyzUiso*/Ueq
S10.63260 (16)0.61227 (9)0.12889 (3)0.0363 (2)
O10.5233 (5)0.7519 (3)0.13349 (12)0.0522 (7)
N10.4626 (5)0.5129 (3)0.17054 (11)0.0370 (7)
C10.4079 (7)0.2576 (4)0.15217 (13)0.0395 (8)
H10.26920.27830.12850.047*
O20.9034 (4)0.5892 (3)0.14085 (9)0.0485 (6)
C20.4814 (6)0.1180 (4)0.16065 (13)0.0431 (8)
H20.38930.04450.14370.052*
O30.7825 (6)−0.0468 (3)0.20338 (12)0.0585 (8)
H30.6871−0.10390.18740.088*
C30.6923 (7)0.0881 (4)0.19449 (13)0.0396 (8)
C40.8231 (7)0.1962 (4)0.22069 (14)0.0433 (9)
H40.96470.17590.24370.052*
C50.7442 (7)0.3353 (4)0.21288 (14)0.0402 (8)
H50.83130.40870.23110.048*
C60.5380 (6)0.3661 (4)0.17841 (12)0.0321 (7)
C70.5766 (6)0.5525 (4)0.06026 (12)0.0351 (7)
C80.3782 (7)0.6111 (4)0.02947 (14)0.0493 (8)
H80.27420.68310.04420.059*
C90.3350 (8)0.5617 (5)−0.02374 (15)0.0595 (11)
H90.20180.6009−0.04520.071*
C100.4879 (8)0.4549 (5)−0.04506 (15)0.0598 (11)
H100.45840.4225−0.08100.072*
C110.6818 (8)0.3963 (5)−0.01419 (16)0.0662 (12)
H110.78340.3233−0.02890.079*
C120.7288 (7)0.4448 (4)0.03900 (14)0.0507 (9)
H120.86200.40490.06020.061*
H1N0.28030.53030.16300.061*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0375 (4)0.0329 (4)0.0385 (4)−0.0016 (4)−0.0041 (3)−0.0002 (4)
O10.0636 (17)0.0303 (12)0.0625 (16)0.0040 (12)−0.0060 (14)−0.0046 (12)
N10.0364 (15)0.0373 (15)0.0373 (13)0.0033 (12)0.0024 (11)0.0021 (13)
C10.0377 (18)0.0422 (19)0.0385 (16)0.0000 (16)−0.0116 (14)0.0006 (15)
O20.0358 (13)0.0577 (16)0.0519 (13)−0.0093 (12)−0.0081 (11)0.0039 (12)
C20.0430 (18)0.0401 (18)0.0463 (17)−0.0019 (17)−0.0108 (14)−0.0059 (18)
O30.072 (2)0.0341 (14)0.0689 (18)0.0048 (14)−0.0216 (14)0.0013 (14)
C30.048 (2)0.0371 (19)0.0340 (16)0.0018 (16)−0.0018 (13)0.0043 (15)
C40.046 (2)0.045 (2)0.0395 (17)−0.0033 (17)−0.0152 (16)0.0063 (16)
C50.0486 (19)0.0345 (18)0.0375 (16)−0.0059 (17)−0.0104 (15)0.0008 (15)
C60.0352 (15)0.0326 (17)0.0284 (13)0.0008 (14)0.0042 (12)0.0024 (13)
C70.0345 (17)0.0343 (17)0.0364 (15)−0.0052 (14)0.0005 (13)0.0036 (14)
C80.0475 (19)0.050 (2)0.0504 (19)0.004 (2)−0.0062 (17)0.0066 (18)
C90.060 (3)0.073 (3)0.046 (2)0.000 (2)−0.0144 (19)0.012 (2)
C100.065 (3)0.078 (3)0.0364 (18)−0.003 (2)0.0001 (18)−0.009 (2)
C110.065 (3)0.084 (3)0.050 (2)0.017 (3)−0.0014 (18)−0.017 (2)
C120.045 (2)0.061 (2)0.0468 (19)0.012 (2)−0.0053 (16)−0.0020 (19)

Geometric parameters (Å, °)

S1—O21.429 (2)C4—H40.9300
S1—O11.430 (3)C5—C61.372 (4)
S1—N11.622 (3)C5—H50.9300
S1—C71.769 (3)C7—C81.371 (5)
N1—C61.445 (4)C7—C121.375 (5)
N1—H1N0.9629C8—C91.381 (5)
C1—C61.371 (5)C8—H80.9300
C1—C21.380 (5)C9—C101.371 (6)
C1—H10.9300C9—H90.9300
C2—C31.380 (4)C10—C111.355 (6)
C2—H20.9300C10—H100.9300
O3—C31.365 (4)C11—C121.381 (5)
O3—H30.8200C11—H110.9300
C3—C41.370 (5)C12—H120.9300
C4—C51.381 (5)
O2—S1—O1120.06 (15)C6—C5—H5119.8
O2—S1—N1107.82 (15)C4—C5—H5119.8
O1—S1—N1105.73 (15)C1—C6—C5119.7 (3)
O2—S1—C7107.28 (15)C1—C6—N1121.3 (3)
O1—S1—C7107.48 (16)C5—C6—N1119.0 (3)
N1—S1—C7107.99 (15)C8—C7—C12120.8 (3)
C6—N1—S1119.2 (2)C8—C7—S1119.9 (3)
C6—N1—H1N116.4C12—C7—S1119.3 (3)
S1—N1—H1N107.6C7—C8—C9119.0 (4)
C6—C1—C2120.4 (3)C7—C8—H8120.5
C6—C1—H1119.8C9—C8—H8120.5
C2—C1—H1119.8C10—C9—C8120.2 (4)
C1—C2—C3119.6 (3)C10—C9—H9119.9
C1—C2—H2120.2C8—C9—H9119.9
C3—C2—H2120.2C11—C10—C9120.5 (4)
C3—O3—H3109.5C11—C10—H10119.7
O3—C3—C4116.8 (3)C9—C10—H10119.7
O3—C3—C2123.1 (3)C10—C11—C12120.2 (4)
C4—C3—C2120.1 (3)C10—C11—H11119.9
C3—C4—C5119.8 (3)C12—C11—H11119.9
C3—C4—H4120.1C7—C12—C11119.3 (3)
C5—C4—H4120.1C7—C12—H12120.3
C6—C5—C4120.4 (3)C11—C12—H12120.3
O2—S1—N1—C6−45.9 (3)O2—S1—C7—C8−152.9 (3)
O1—S1—N1—C6−175.5 (2)O1—S1—C7—C8−22.5 (3)
C7—S1—N1—C669.7 (3)N1—S1—C7—C891.1 (3)
C6—C1—C2—C3−2.0 (5)O2—S1—C7—C1228.9 (3)
C1—C2—C3—O3−177.7 (3)O1—S1—C7—C12159.3 (3)
C1—C2—C3—C41.8 (5)N1—S1—C7—C12−87.1 (3)
O3—C3—C4—C5179.1 (3)C12—C7—C8—C9−0.9 (6)
C2—C3—C4—C5−0.4 (5)S1—C7—C8—C9−179.1 (3)
C3—C4—C5—C6−0.9 (5)C7—C8—C9—C100.4 (6)
C2—C1—C6—C50.7 (5)C8—C9—C10—C110.3 (6)
C2—C1—C6—N1−179.4 (3)C9—C10—C11—C12−0.6 (7)
C4—C5—C6—C10.8 (5)C8—C7—C12—C110.6 (5)
C4—C5—C6—N1−179.2 (3)S1—C7—C12—C11178.8 (3)
S1—N1—C6—C1−101.5 (3)C10—C11—C12—C70.2 (6)
S1—N1—C6—C578.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.962.073.030 (3)173
O3—H3···O1ii0.822.052.857 (4)166

Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5239).

References

  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Khan, I. U., Haider, Z., Zia-ur-Rehman, M., Arshad, M. N. & Shafiq, M. (2009). Acta Cryst. E65, o2867. [PMC free article] [PubMed]
  • Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst.39, 453–457.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Zia-ur-Rehman, M. Z., Choudary, J. A., Ahmad, S. & Siddiqui, H. L. (2006). Chem. Pharm. Bull.54, 1175–1178. [PubMed]
  • Zia-ur-Rehman, M., Choudary, J. A., Elsegood, M. R. J., Siddiqui, H. L. & Khan, K. M. (2009). Eur. J. Med. Chem.44, 1311–1316. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography