N -(4-Hydroxyphenyl)benzenesulfonamide

organic compounds Acta Crystallographica Section E Data collection Structure Reports Online 2808 independent reflections 2076 reflections with I > 2(I) Rint = 0.032 Bruker APEXII CCD area-detector diffractometer 6402 measured reflections ISSN 1600-5368 Refinement N-(4-Hydroxyphenyl)benzenesulfonamide Islam Ullah Khan,a Irfana Mariam,a Muhammad Zia-urRehman,b* Muhammad Arif Sajjada and Shahzad Sharifa a Materials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan, and bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan Correspondence e-mail: rehman_pcsir@hotmail.com R[F 2 > 2(F 2)] = 0.048 wR(F 2) = 0.146 S = 1.02 2808 reflections 155 parameters H-atom parameters constrained Table 1 Hydrogen-bond geometry (Å,  ). D—H


A i N1—H1N


O2 O3—H3


O1ii Received 31 March 2010; accepted 9 April 2010 Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.005 Å; R factor = 0.048; wR factor = 0.146; data-to-parameter ratio = 18.1. 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, 2009). For a related structure, see: Khan et al. (2009).
max = 0.26 e Å 3
min = 0.26 e Å 3 Absolute structure: Flack (1983), with 1118 Friedel pairs Flack parameter: 0.08 (13) Symmetry codes: (i) x D—H H


A D


A D—H


A 0.96 0.82 2.07 2.05 3.030 (3) 2.857 (4) 173 166 1; y; z; (ii) x; y 1; z. 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: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON. The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5239). References Experimental Crystal data C12H11NO3S Mr = 249.28 Orthorhombic, P21 21 21 a = 5.1072 (2) Å b = 9.3948 (4) Å c = 24.0903 (10) Å o1088 Khan et al. V = 1155.88 (8) Å3 Z=4 Mo K radiation  = 0.28 mm 1 T = 296 K 0.12  0.12  0.10 mm 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. 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. Spek, A. L. (2009). Acta Cryst. D65, 148–155. Zia-ur-Rehman, M. Z., Choudary, J. A., Ahmad, S. & Siddiqui, H. L. (2006). Chem. Pharm. Bull. 54, 1175–1178. 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. doi:10.1107/S160053681001322X Acta Cryst. (2010). E66, o1088 supplementary materials supplementary materials Acta Cryst. (2010). E66, o1088 [ doi:10.1107/S160053681001322X ] N-(4-Hydroxyphenyl)benzenesulfonamide I. U. Khan, I. Mariam, M. Zia-ur-Rehman, M. Arif Sajjad and S. Sharif 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-urRehman 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. sup-1 supplementary materials 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. N-(4-Hydroxyphenyl)benzenesulfonamide Crystal data C12H11NO3S F(000) = 520 Mr = 249.28 Dx = 1.432 Mg m−3 Orthorhombic, P212121 Mo Kα radiation, λ = 0.71073 Å Hall symbol: P 2ac 2ab a = 5.1072 (2) Å Cell parameters from 6462 reflections θ = 2.5–27.1° b = 9.3948 (4) Å µ = 0.28 mm−1 T = 296 K c = 24.0903 (10) Å V = 1155.88 (8) Å3 Z=4 Needle, colourless 0.12 × 0.12 × 0.10 mm Data collection Bruker APEXII CCD area-detector diffractometer 2076 reflections with I > 2σ(I) Radiation source: fine-focus sealed tube Rint = 0.032 graphite θmax = 28.3°, θmin = 1.7° φ and ω scans 6402 measured reflections 2808 independent reflections h = −4→6 k = −8→12 l = −32→32 Refinement 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)] = 0.048 H-atom parameters constrained wR(F2) = 0.146 w = 1/[σ2(Fo2) + (0.0829P)2] where P = (Fo2 + 2Fc2)/3 S = 1.02 (Δ/σ)max < 0.001 2808 reflections Δρmax = 0.26 e Å−3 155 parameters Δρmin = −0.26 e Å−3 sup-2 supplementary materials 0 restraints Absolute structure: Flack (1983), 1118 Friedel pairs Primary atom site location: structure-invariant direct Flack parameter: 0.08 (13) methods 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 Rfactors(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) S1 O1 N1 C1 H1 O2 C2 H2 O3 H3 C3 C4 H4 C5 H5 C6 C7 C8 H8 C9 H9 C10 H10 C11 H11 C12 H12 H1N x y z Uiso*/Ueq 0.63260 (16) 0.5233 (5) 0.4626 (5) 0.4079 (7) 0.2692 0.9034 (4) 0.4814 (6) 0.3893 0.7825 (6) 0.6871 0.6923 (7) 0.8231 (7) 0.9647 0.7442 (7) 0.8313 0.5380 (6) 0.5766 (6) 0.3782 (7) 0.2742 0.3350 (8) 0.2018 0.4879 (8) 0.4584 0.6818 (8) 0.7834 0.7288 (7) 0.8620 0.2803 0.61227 (9) 0.7519 (3) 0.5129 (3) 0.2576 (4) 0.2783 0.5892 (3) 0.1180 (4) 0.0445 −0.0468 (3) −0.1039 0.0881 (4) 0.1962 (4) 0.1759 0.3353 (4) 0.4087 0.3661 (4) 0.5525 (4) 0.6111 (4) 0.6831 0.5617 (5) 0.6009 0.4549 (5) 0.4225 0.3963 (5) 0.3233 0.4448 (4) 0.4049 0.5303 0.12889 (3) 0.13349 (12) 0.17054 (11) 0.15217 (13) 0.1285 0.14085 (9) 0.16065 (13) 0.1437 0.20338 (12) 0.1874 0.19449 (13) 0.22069 (14) 0.2437 0.21288 (14) 0.2311 0.17841 (12) 0.06026 (12) 0.02947 (14) 0.0442 −0.02374 (15) −0.0452 −0.04506 (15) −0.0810 −0.01419 (16) −0.0289 0.03900 (14) 0.0602 0.1630 0.0363 (2) 0.0522 (7) 0.0370 (7) 0.0395 (8) 0.047* 0.0485 (6) 0.0431 (8) 0.052* 0.0585 (8) 0.088* 0.0396 (8) 0.0433 (9) 0.052* 0.0402 (8) 0.048* 0.0321 (7) 0.0351 (7) 0.0493 (8) 0.059* 0.0595 (11) 0.071* 0.0598 (11) 0.072* 0.0662 (12) 0.079* 0.0507 (9) 0.061* 0.061* sup-3 supplementary materials Atomic displacement parameters (Å2) S1 O1 N1 C1 O2 C2 O3 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 U11 0.0375 (4) 0.0636 (17) 0.0364 (15) 0.0377 (18) 0.0358 (13) 0.0430 (18) 0.072 (2) 0.048 (2) 0.046 (2) 0.0486 (19) 0.0352 (15) 0.0345 (17) 0.0475 (19) 0.060 (3) 0.065 (3) 0.065 (3) 0.045 (2) U22 0.0329 (4) 0.0303 (12) 0.0373 (15) 0.0422 (19) 0.0577 (16) 0.0401 (18) 0.0341 (14) 0.0371 (19) 0.045 (2) 0.0345 (18) 0.0326 (17) 0.0343 (17) 0.050 (2) 0.073 (3) 0.078 (3) 0.084 (3) 0.061 (2) U33 0.0385 (4) 0.0625 (16) 0.0373 (13) 0.0385 (16) 0.0519 (13) 0.0463 (17) 0.0689 (18) 0.0340 (16) 0.0395 (17) 0.0375 (16) 0.0284 (13) 0.0364 (15) 0.0504 (19) 0.046 (2) 0.0364 (18) 0.050 (2) 0.0468 (19) U12 −0.0016 (4) 0.0040 (12) 0.0033 (12) 0.0000 (16) −0.0093 (12) −0.0019 (17) 0.0048 (14) 0.0018 (16) −0.0033 (17) −0.0059 (17) 0.0008 (14) −0.0052 (14) 0.004 (2) 0.000 (2) −0.003 (2) 0.017 (3) 0.012 (2) U13 −0.0041 (3) −0.0060 (14) 0.0024 (11) −0.0116 (14) −0.0081 (11) −0.0108 (14) −0.0216 (14) −0.0018 (13) −0.0152 (16) −0.0104 (15) 0.0042 (12) 0.0005 (13) −0.0062 (17) −0.0144 (19) 0.0001 (18) −0.0014 (18) −0.0053 (16) U23 −0.0002 (4) −0.0046 (12) 0.0021 (13) 0.0006 (15) 0.0039 (12) −0.0059 (18) 0.0013 (14) 0.0043 (15) 0.0063 (16) 0.0008 (15) 0.0024 (13) 0.0036 (14) 0.0066 (18) 0.012 (2) −0.009 (2) −0.017 (2) −0.0020 (19) Geometric parameters (Å, °) S1—O2 S1—O1 S1—N1 S1—C7 N1—C6 N1—H1N C1—C6 C1—C2 C1—H1 C2—C3 C2—H2 O3—C3 O3—H3 C3—C4 C4—C5 1.429 (2) 1.430 (3) 1.622 (3) 1.769 (3) 1.445 (4) 0.9629 1.371 (5) 1.380 (5) 0.9300 1.380 (4) 0.9300 1.365 (4) 0.8200 1.370 (5) 1.381 (5) C4—H4 C5—C6 C5—H5 C7—C8 C7—C12 C8—C9 C8—H8 C9—C10 C9—H9 C10—C11 C10—H10 C11—C12 C11—H11 C12—H12 0.9300 1.372 (4) 0.9300 1.371 (5) 1.375 (5) 1.381 (5) 0.9300 1.371 (6) 0.9300 1.355 (6) 0.9300 1.381 (5) 0.9300 0.9300 O2—S1—O1 O2—S1—N1 O1—S1—N1 O2—S1—C7 O1—S1—C7 N1—S1—C7 C6—N1—S1 C6—N1—H1N S1—N1—H1N 120.06 (15) 107.82 (15) 105.73 (15) 107.28 (15) 107.48 (16) 107.99 (15) 119.2 (2) 116.4 107.6 C6—C5—H5 C4—C5—H5 C1—C6—C5 C1—C6—N1 C5—C6—N1 C8—C7—C12 C8—C7—S1 C12—C7—S1 C7—C8—C9 119.8 119.8 119.7 (3) 121.3 (3) 119.0 (3) 120.8 (3) 119.9 (3) 119.3 (3) 119.0 (4) sup-4 supplementary materials C6—C1—C2 C6—C1—H1 C2—C1—H1 C1—C2—C3 C1—C2—H2 C3—C2—H2 C3—O3—H3 O3—C3—C4 O3—C3—C2 C4—C3—C2 C3—C4—C5 C3—C4—H4 C5—C4—H4 C6—C5—C4 120.4 (3) 119.8 119.8 119.6 (3) 120.2 120.2 109.5 116.8 (3) 123.1 (3) 120.1 (3) 119.8 (3) 120.1 120.1 120.4 (3) C7—C8—H8 C9—C8—H8 C10—C9—C8 C10—C9—H9 C8—C9—H9 C11—C10—C9 C11—C10—H10 C9—C10—H10 C10—C11—C12 C10—C11—H11 C12—C11—H11 C7—C12—C11 C7—C12—H12 C11—C12—H12 120.5 120.5 120.2 (4) 119.9 119.9 120.5 (4) 119.7 119.7 120.2 (4) 119.9 119.9 119.3 (3) 120.3 120.3 O2—S1—N1—C6 O1—S1—N1—C6 C7—S1—N1—C6 C6—C1—C2—C3 C1—C2—C3—O3 C1—C2—C3—C4 O3—C3—C4—C5 C2—C3—C4—C5 C3—C4—C5—C6 C2—C1—C6—C5 C2—C1—C6—N1 C4—C5—C6—C1 C4—C5—C6—N1 S1—N1—C6—C1 S1—N1—C6—C5 −45.9 (3) −175.5 (2) 69.7 (3) −2.0 (5) −177.7 (3) 1.8 (5) 179.1 (3) −0.4 (5) −0.9 (5) 0.7 (5) −179.4 (3) 0.8 (5) −179.2 (3) −101.5 (3) 78.5 (3) O2—S1—C7—C8 O1—S1—C7—C8 N1—S1—C7—C8 O2—S1—C7—C12 O1—S1—C7—C12 N1—S1—C7—C12 C12—C7—C8—C9 S1—C7—C8—C9 C7—C8—C9—C10 C8—C9—C10—C11 C9—C10—C11—C12 C8—C7—C12—C11 S1—C7—C12—C11 C10—C11—C12—C7 −152.9 (3) −22.5 (3) 91.1 (3) 28.9 (3) 159.3 (3) −87.1 (3) −0.9 (6) −179.1 (3) 0.4 (6) 0.3 (6) −0.6 (7) 0.6 (5) 178.8 (3) 0.2 (6) Hydrogen-bond geometry (Å, °) D—H···A N1—H1N···O2 ii i O3—H3···O1 Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z. D—H H···A D···A D—H···A 0.96 2.07 3.030 (3) 173. 0.82 2.05 2.857 (4) 166. sup-5 supplementary materials Fig. 1 sup-6 supplementary materials Fig. 2 sup-7