organic compounds
N-(2-Hydroxyphenyl)-4-methylbenzenesulfonamide
aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, dSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, Wales, eDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
In the title compound, C13H13NO3S, the dihedral angle between the benzene rings is 64.15 (7)° and the C—S—N—C torsion angle is −57.18 (12)°. An intramolecular N—H⋯O hydrogen bond closes an S(5) ring. In the crystal, O—H⋯O hydrogen bonds link the molecules into C(8) chains propagating in [100]. Weak C—H⋯π interactions are also observed.
CCDC reference: 976171
Related literature
For background to the biological activity of sulfonamide compounds, see: Ozbek et al. (2007); El-Sayed et al. (2011). For related structures, see: Gowda et al. (2008a,b,c).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Oxford Diffraction, 2013); cell CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 976171
https://doi.org/10.1107/S1600536813033394/hb7173sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033394/hb7173Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536813033394/hb7173Isup3.cml
A mixture of 2-aminophenol (109 mg, 1 mmol) and p-toluenesulfonyl chloride (190 mg, 1 mmol) in 10 ml dioxane with addition of few drops of triethylamine as a catalyst, was refluxed for 4 h. The reaction mixture was left to cool at ambient temperature where the solid product was deposited, collected by filteration and recrystallized from ethanol in 91% yield. Brown needles were grown from ethanol solution over 3 days at room temperature. M.p. 391 K.
The H atoms of the NH and OH groups were found from difference Fourier maps and refined freely. The C-bound H atoms were positioned geometrically, with C—H = 0.95 and 0.98 Å and refined as riding with Uiso(H) = 1.Ueq(C) for the methyl H atoms and Uiso(H) = 1.2Ueq(C) for the other H atoms.
The biological activities of sulphonamide compounds are well documented, for example as antimicrobial (Ozbek et al., 2007) and anticancer (El-Sayed et al., 2011) agents. Further to our interest in related compounds with potential biactivity, we now report the synthesis and
of the title compound.The benzene rings (C1–C6 and C8–C13) of the title compound (I) in Fig. 1 make a dihedral angle of 64.15 (7)° with each other. The bridge C1—S1—N1—C8 torsion angle between the benzene rings is -57.18 (12)°. The O1–S1–O2 and C1–S1–N1 angles are 119.78 (6) and 107.97 (6)°, respectively. The bond lengths and angles are similar to those in related structures (Gowda et al., 2008a,b,c).
The π interactions are also observed (Table 1).
features an N—H···O hydrogen bond which forms an S(5) ring (Fig. 2). In the crystal, molecules are linked by O—H···O hydrogen bonds into C(8) chains along [100] (Figs. 2 and 3). Weak C—H···For background to the biological activity of sulfonamide compounds, see: Ozbek et al. (2007); El-Sayed et al. (2011). For related structures, see: Gowda et al. (2008a,b,c).
Data collection: CrysAlis PRO (Oxford Diffraction, 2013); cell
CrysAlis PRO (Oxford Diffraction, 2013); data reduction: CrysAlis PRO (Oxford Diffraction, 2013); 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).Fig. 1. View of the title compound with displacement ellipsoids for non-H atoms drawn at the 50% probability level. | |
Fig. 2. View of the hydrogen bonds along the a axis direction of the title compound. H bonds are shown as dashed lines. | |
Fig. 3. View of the molecular packing along the a axis of the title compound. H bonds are shown as dashed lines. |
C13H13NO3S | F(000) = 552 |
Mr = 263.31 | Dx = 1.417 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ybc | Cell parameters from 2248 reflections |
a = 7.6780 (1) Å | θ = 5.1–73.2° |
b = 15.4747 (3) Å | µ = 2.34 mm−1 |
c = 10.7250 (2) Å | T = 120 K |
β = 104.333 (2)° | Needle, brown |
V = 1234.62 (4) Å3 | 0.35 × 0.16 × 0.13 mm |
Z = 4 |
Oxford Diffraction SuperNova (Dual, Cu at zero, Atlas) diffractometer | 2377 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 2248 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.011 |
ω scans | θmax = 73.2°, θmin = 5.1° |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2013) | h = −8→9 |
Tmin = 0.494, Tmax = 0.750 | k = −19→12 |
4355 measured reflections | l = −11→13 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.082 | W = 1/[Σ2(FO2) + (0.0424P)2 + 0.5981P] where P = (FO2 + 2FC2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
2377 reflections | Δρmax = 0.28 e Å−3 |
172 parameters | Δρmin = −0.38 e Å−3 |
C13H13NO3S | V = 1234.62 (4) Å3 |
Mr = 263.31 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 7.6780 (1) Å | µ = 2.34 mm−1 |
b = 15.4747 (3) Å | T = 120 K |
c = 10.7250 (2) Å | 0.35 × 0.16 × 0.13 mm |
β = 104.333 (2)° |
Oxford Diffraction SuperNova (Dual, Cu at zero, Atlas) diffractometer | 2377 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2013) | 2248 reflections with I > 2σ(I) |
Tmin = 0.494, Tmax = 0.750 | Rint = 0.011 |
4355 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.28 e Å−3 |
2377 reflections | Δρmin = −0.38 e Å−3 |
172 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 | 0.51287 (4) | 0.65871 (2) | 0.83597 (3) | 0.0203 (1) | |
O1 | 0.57618 (13) | 0.61174 (7) | 0.95358 (10) | 0.0281 (3) | |
O2 | 0.63687 (13) | 0.70958 (7) | 0.78545 (10) | 0.0267 (3) | |
O3 | 0.00824 (14) | 0.71635 (7) | 0.81974 (10) | 0.0264 (3) | |
N1 | 0.36177 (15) | 0.72621 (8) | 0.86360 (11) | 0.0208 (3) | |
C1 | 0.40408 (17) | 0.58685 (9) | 0.71468 (13) | 0.0196 (4) | |
C2 | 0.3833 (2) | 0.60851 (9) | 0.58584 (14) | 0.0239 (4) | |
C3 | 0.2974 (2) | 0.55124 (10) | 0.49170 (14) | 0.0268 (4) | |
C4 | 0.23172 (19) | 0.47243 (9) | 0.52309 (14) | 0.0247 (4) | |
C5 | 0.2521 (2) | 0.45305 (10) | 0.65261 (15) | 0.0278 (4) | |
C6 | 0.3373 (2) | 0.50922 (10) | 0.74888 (14) | 0.0253 (4) | |
C7 | 0.1447 (2) | 0.40915 (11) | 0.42031 (17) | 0.0343 (5) | |
C8 | 0.25492 (18) | 0.77847 (9) | 0.76315 (13) | 0.0192 (3) | |
C9 | 0.3290 (2) | 0.83739 (9) | 0.69307 (15) | 0.0243 (4) | |
C10 | 0.2174 (2) | 0.89020 (9) | 0.60237 (15) | 0.0273 (4) | |
C11 | 0.0320 (2) | 0.88327 (10) | 0.58080 (14) | 0.0265 (4) | |
C12 | −0.04291 (19) | 0.82447 (10) | 0.65038 (14) | 0.0234 (4) | |
C13 | 0.06818 (18) | 0.77298 (9) | 0.74268 (13) | 0.0202 (3) | |
H1N | 0.301 (3) | 0.7023 (13) | 0.9076 (19) | 0.035 (5)* | |
H1O | −0.106 (3) | 0.7191 (15) | 0.807 (2) | 0.051 (6)* | |
H2 | 0.42760 | 0.66200 | 0.56290 | 0.0290* | |
H3 | 0.28280 | 0.56590 | 0.40370 | 0.0320* | |
H5 | 0.20630 | 0.39990 | 0.67550 | 0.0330* | |
H6 | 0.35000 | 0.49500 | 0.83680 | 0.0300* | |
H7A | 0.22220 | 0.35830 | 0.42470 | 0.0510* | |
H7B | 0.12710 | 0.43650 | 0.33560 | 0.0510* | |
H7C | 0.02810 | 0.39140 | 0.43350 | 0.0510* | |
H9 | 0.45580 | 0.84160 | 0.70710 | 0.0290* | |
H10 | 0.26800 | 0.93100 | 0.55520 | 0.0330* | |
H11 | −0.04390 | 0.91890 | 0.51810 | 0.0320* | |
H12 | −0.16980 | 0.81950 | 0.63480 | 0.0280* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0117 (2) | 0.0246 (2) | 0.0243 (2) | 0.0002 (1) | 0.0036 (1) | −0.0013 (1) |
O1 | 0.0198 (5) | 0.0360 (6) | 0.0254 (5) | 0.0033 (4) | −0.0005 (4) | 0.0019 (4) |
O2 | 0.0140 (5) | 0.0298 (5) | 0.0380 (6) | −0.0027 (4) | 0.0096 (4) | −0.0031 (4) |
O3 | 0.0146 (5) | 0.0354 (6) | 0.0298 (5) | −0.0019 (4) | 0.0068 (4) | 0.0060 (4) |
N1 | 0.0150 (5) | 0.0253 (6) | 0.0229 (6) | −0.0006 (5) | 0.0065 (5) | −0.0022 (5) |
C1 | 0.0154 (6) | 0.0207 (6) | 0.0233 (7) | 0.0027 (5) | 0.0059 (5) | −0.0003 (5) |
C2 | 0.0258 (7) | 0.0208 (7) | 0.0269 (7) | 0.0013 (5) | 0.0101 (6) | 0.0031 (5) |
C3 | 0.0308 (8) | 0.0275 (7) | 0.0232 (7) | 0.0035 (6) | 0.0089 (6) | 0.0008 (6) |
C4 | 0.0197 (6) | 0.0247 (7) | 0.0302 (7) | 0.0040 (6) | 0.0071 (6) | −0.0042 (6) |
C5 | 0.0280 (8) | 0.0210 (7) | 0.0359 (8) | −0.0025 (6) | 0.0107 (6) | 0.0019 (6) |
C6 | 0.0264 (7) | 0.0254 (7) | 0.0247 (7) | 0.0003 (6) | 0.0074 (6) | 0.0047 (6) |
C7 | 0.0288 (8) | 0.0334 (8) | 0.0404 (9) | −0.0004 (7) | 0.0081 (7) | −0.0130 (7) |
C8 | 0.0171 (6) | 0.0196 (6) | 0.0211 (6) | −0.0004 (5) | 0.0052 (5) | −0.0056 (5) |
C9 | 0.0206 (7) | 0.0230 (7) | 0.0319 (7) | −0.0026 (5) | 0.0112 (6) | −0.0047 (6) |
C10 | 0.0317 (8) | 0.0223 (7) | 0.0313 (8) | −0.0011 (6) | 0.0144 (6) | 0.0009 (6) |
C11 | 0.0292 (8) | 0.0243 (7) | 0.0260 (7) | 0.0048 (6) | 0.0069 (6) | 0.0001 (6) |
C12 | 0.0178 (6) | 0.0268 (7) | 0.0255 (7) | 0.0018 (5) | 0.0051 (5) | −0.0041 (6) |
C13 | 0.0186 (6) | 0.0213 (6) | 0.0220 (6) | −0.0023 (5) | 0.0076 (5) | −0.0050 (5) |
S1—O1 | 1.4325 (11) | C8—C9 | 1.390 (2) |
S1—O2 | 1.4405 (11) | C9—C10 | 1.391 (2) |
S1—N1 | 1.6417 (12) | C10—C11 | 1.389 (2) |
S1—C1 | 1.7574 (14) | C11—C12 | 1.389 (2) |
O3—C13 | 1.3606 (18) | C12—C13 | 1.387 (2) |
O3—H1O | 0.86 (2) | C2—H2 | 0.9500 |
N1—C8 | 1.4318 (18) | C3—H3 | 0.9500 |
N1—H1N | 0.83 (2) | C5—H5 | 0.9500 |
C1—C6 | 1.391 (2) | C6—H6 | 0.9500 |
C1—C2 | 1.392 (2) | C7—H7A | 0.9800 |
C2—C3 | 1.382 (2) | C7—H7B | 0.9800 |
C3—C4 | 1.393 (2) | C7—H7C | 0.9800 |
C4—C7 | 1.502 (2) | C9—H9 | 0.9500 |
C4—C5 | 1.392 (2) | C10—H10 | 0.9500 |
C5—C6 | 1.384 (2) | C11—H11 | 0.9500 |
C8—C13 | 1.398 (2) | C12—H12 | 0.9500 |
O1—S1—O2 | 119.78 (6) | C11—C12—C13 | 119.77 (14) |
O1—S1—N1 | 105.36 (6) | O3—C13—C8 | 115.57 (12) |
O1—S1—C1 | 109.04 (6) | O3—C13—C12 | 124.25 (13) |
O2—S1—N1 | 106.42 (6) | C8—C13—C12 | 120.17 (13) |
O2—S1—C1 | 107.74 (6) | C1—C2—H2 | 120.00 |
N1—S1—C1 | 107.97 (6) | C3—C2—H2 | 120.00 |
C13—O3—H1O | 111.0 (15) | C2—C3—H3 | 119.00 |
S1—N1—C8 | 121.50 (9) | C4—C3—H3 | 119.00 |
C8—N1—H1N | 112.5 (15) | C4—C5—H5 | 119.00 |
S1—N1—H1N | 110.0 (15) | C6—C5—H5 | 119.00 |
S1—C1—C6 | 119.35 (11) | C1—C6—H6 | 121.00 |
S1—C1—C2 | 119.94 (11) | C5—C6—H6 | 121.00 |
C2—C1—C6 | 120.71 (13) | C4—C7—H7A | 109.00 |
C1—C2—C3 | 119.17 (13) | C4—C7—H7B | 109.00 |
C2—C3—C4 | 121.39 (14) | C4—C7—H7C | 109.00 |
C5—C4—C7 | 120.78 (13) | H7A—C7—H7B | 109.00 |
C3—C4—C5 | 118.17 (13) | H7A—C7—H7C | 109.00 |
C3—C4—C7 | 121.03 (13) | H7B—C7—H7C | 109.00 |
C4—C5—C6 | 121.67 (14) | C8—C9—H9 | 120.00 |
C1—C6—C5 | 118.87 (13) | C10—C9—H9 | 120.00 |
N1—C8—C9 | 122.85 (13) | C9—C10—H10 | 120.00 |
N1—C8—C13 | 117.26 (12) | C11—C10—H10 | 120.00 |
C9—C8—C13 | 119.73 (13) | C10—C11—H11 | 120.00 |
C8—C9—C10 | 119.99 (14) | C12—C11—H11 | 120.00 |
C9—C10—C11 | 119.98 (14) | C11—C12—H12 | 120.00 |
C10—C11—C12 | 120.33 (14) | C13—C12—H12 | 120.00 |
O1—S1—N1—C8 | −173.59 (11) | C2—C3—C4—C7 | −177.69 (15) |
O2—S1—N1—C8 | 58.25 (12) | C2—C3—C4—C5 | 1.0 (2) |
C1—S1—N1—C8 | −57.18 (12) | C3—C4—C5—C6 | −1.0 (2) |
O1—S1—C1—C2 | −158.83 (12) | C7—C4—C5—C6 | 177.79 (15) |
O2—S1—C1—C2 | −27.38 (14) | C4—C5—C6—C1 | −0.1 (2) |
N1—S1—C1—C2 | 87.19 (13) | N1—C8—C9—C10 | −175.85 (13) |
O1—S1—C1—C6 | 22.08 (14) | C13—C8—C9—C10 | −0.4 (2) |
O2—S1—C1—C6 | 153.53 (12) | N1—C8—C13—O3 | −1.43 (18) |
N1—S1—C1—C6 | −91.91 (13) | N1—C8—C13—C12 | 177.40 (13) |
S1—N1—C8—C9 | −59.30 (17) | C9—C8—C13—O3 | −177.10 (13) |
S1—N1—C8—C13 | 125.18 (12) | C9—C8—C13—C12 | 1.7 (2) |
S1—C1—C6—C5 | −179.91 (12) | C8—C9—C10—C11 | −0.8 (2) |
S1—C1—C2—C3 | −180.00 (12) | C9—C10—C11—C12 | 0.7 (2) |
C6—C1—C2—C3 | −0.9 (2) | C10—C11—C12—C13 | 0.6 (2) |
C2—C1—C6—C5 | 1.0 (2) | C11—C12—C13—O3 | 176.92 (13) |
C1—C2—C3—C4 | −0.1 (2) | C11—C12—C13—C8 | −1.8 (2) |
Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3 | 0.83 (2) | 2.22 (2) | 2.6420 (16) | 111.6 (17) |
O3—H1O···O2i | 0.86 (2) | 1.94 (2) | 2.7852 (15) | 172 (2) |
C9—H9···O2 | 0.95 | 2.50 | 3.0531 (18) | 117 |
C3—H3···Cg2ii | 0.95 | 2.92 | 3.8022 (16) | 155 |
C7—H7C···Cg1iii | 0.98 | 2.85 | 3.5937 (17) | 134 |
Symmetry codes: (i) x−1, y, z; (ii) x, −y+3/2, z−1/2; (iii) −x, −y+1, −z+1. |
Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3 | 0.83 (2) | 2.22 (2) | 2.6420 (16) | 111.6 (17) |
O3—H1O···O2i | 0.86 (2) | 1.94 (2) | 2.7852 (15) | 172 (2) |
C3—H3···Cg2ii | 0.95 | 2.92 | 3.8022 (16) | 155 |
C7—H7C···Cg1iii | 0.98 | 2.85 | 3.5937 (17) | 134 |
Symmetry codes: (i) x−1, y, z; (ii) x, −y+3/2, z−1/2; (iii) −x, −y+1, −z+1. |
Acknowledgements
We thank Manchester Metropolitan University, Erciyes University and Cardiff University for supporting this study.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The biological activities of sulphonamide compounds are well documented, for example as antimicrobial (Ozbek et al., 2007) and anticancer (El-Sayed et al., 2011) agents. Further to our interest in related compounds with potential biactivity, we now report the synthesis and crystal structure of the title compound.
The benzene rings (C1–C6 and C8–C13) of the title compound (I) in Fig. 1 make a dihedral angle of 64.15 (7)° with each other. The bridge C1—S1—N1—C8 torsion angle between the benzene rings is -57.18 (12)°. The O1–S1–O2 and C1–S1–N1 angles are 119.78 (6) and 107.97 (6)°, respectively. The bond lengths and angles are similar to those in related structures (Gowda et al., 2008a,b,c).
The molecular conformation features an N—H···O hydrogen bond which forms an S(5) ring (Fig. 2). In the crystal, molecules are linked by O—H···O hydrogen bonds into C(8) chains along [100] (Figs. 2 and 3). Weak C—H···π interactions are also observed (Table 1).