organic compounds
4-Methyl-N-(4-methylphenyl)benzenesulfonamide
aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan, and bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr
In the title compound, C14H15NO2S, the two aromatic rings enclose a dihedral angle of 70.53 (10)°. A weak intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.
Related literature
For the synthesis, see: Deng & Mani (2006). For the biological activity of see: Pandya et al. (2003); Supuran & Scozzafava (2000). For the effects of substituents on the crystal structures of and bond lengths in aryl see: Sharif et al. (2010); Gowda et al. (2008, 2009, 2010); Nirmala et al. (2009a,b)·For graph-set notation, see: Bernstein et al. (1995); Etter (1990).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell 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).
Supporting information
10.1107/S1600536810008329/bt5205sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810008329/bt5205Isup2.hkl
The synthesis of the title compound was performed by the procedure reported by Deng & Mani (2006). 4-methyl aniline 0.535 g (5 mmol) was dissolved in 10 ml distilled water and pH of the solution was adjusted to 8 by using (3 M) Na2CO3. p-toluene sulfonyl chloride 0.95 g (5 mmol) was added under continuous stirring at room temperature. pH of the reaction mixture during stirring was maintained between 8-9 with 3 M Na2CO3. When the solution was clear, pH was adjusted to 2-3 using 3 M HCl. The precipitate formed was filtered and recrystallized from methanol.
The H atom bonded to N was refined freely. The other H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H = 0.93-0.96 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).C14H15NO2S | Z = 2 |
Mr = 261.34 | F(000) = 276 |
Triclinic, P1 | Dx = 1.312 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.6419 (8) Å | Cell parameters from 3233 reflections |
b = 8.8016 (8) Å | θ = 2.4–25.6° |
c = 9.2509 (7) Å | µ = 0.24 mm−1 |
α = 88.187 (4)° | T = 296 K |
β = 77.010 (4)° | Rod like, light brown |
γ = 74.812 (4)° | 0.28 × 0.17 × 0.08 mm |
V = 661.41 (10) Å3 |
Bruker APEXII CCD diffractometer | 2323 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 28.4°, θmin = 3.4° |
ϕ and ω scans | h = −11→11 |
11831 measured reflections | k = −11→11 |
3259 independent reflections | l = −11→12 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0642P)2 + 0.0376P] where P = (Fo2 + 2Fc2)/3 |
3259 reflections | (Δ/σ)max < 0.001 |
169 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C14H15NO2S | γ = 74.812 (4)° |
Mr = 261.34 | V = 661.41 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.6419 (8) Å | Mo Kα radiation |
b = 8.8016 (8) Å | µ = 0.24 mm−1 |
c = 9.2509 (7) Å | T = 296 K |
α = 88.187 (4)° | 0.28 × 0.17 × 0.08 mm |
β = 77.010 (4)° |
Bruker APEXII CCD diffractometer | 2323 reflections with I > 2σ(I) |
11831 measured reflections | Rint = 0.038 |
3259 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.24 e Å−3 |
3259 reflections | Δρmin = −0.21 e Å−3 |
169 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 esds 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 | 0.18536 (5) | 0.76639 (5) | 0.92202 (4) | 0.0448 (2) | |
O1 | 0.34628 (15) | 0.66385 (16) | 0.90275 (15) | 0.0579 (4) | |
O2 | 0.10049 (15) | 0.83328 (15) | 1.06641 (12) | 0.0537 (4) | |
N1 | 0.1950 (2) | 0.91823 (19) | 0.81866 (16) | 0.0471 (5) | |
C1 | 0.4564 (3) | 0.9071 (3) | 0.1918 (2) | 0.0860 (9) | |
C2 | 0.3869 (3) | 0.9072 (3) | 0.3562 (2) | 0.0589 (7) | |
C3 | 0.4706 (3) | 0.8100 (3) | 0.4474 (2) | 0.0635 (7) | |
C4 | 0.4115 (2) | 0.8091 (2) | 0.5988 (2) | 0.0570 (7) | |
C5 | 0.2605 (2) | 0.9077 (2) | 0.66194 (18) | 0.0423 (5) | |
C6 | 0.1743 (2) | 1.0070 (2) | 0.5727 (2) | 0.0559 (6) | |
C7 | 0.2379 (3) | 1.0074 (3) | 0.4220 (2) | 0.0661 (8) | |
C8 | 0.0609 (2) | 0.66738 (19) | 0.85725 (18) | 0.0428 (5) | |
C9 | 0.1315 (2) | 0.5487 (2) | 0.7513 (2) | 0.0608 (7) | |
C10 | 0.0316 (3) | 0.4755 (2) | 0.6978 (2) | 0.0668 (8) | |
C11 | −0.1361 (2) | 0.5162 (2) | 0.7502 (2) | 0.0526 (6) | |
C12 | −0.2036 (2) | 0.6345 (2) | 0.8566 (2) | 0.0597 (7) | |
C13 | −0.1067 (2) | 0.7097 (2) | 0.9103 (2) | 0.0566 (7) | |
C14 | −0.2439 (3) | 0.4335 (3) | 0.6927 (2) | 0.0702 (8) | |
H1 | 0.118 (3) | 0.994 (3) | 0.843 (2) | 0.068 (7)* | |
H1A | 0.52890 | 0.97510 | 0.17190 | 0.1290* | |
H1B | 0.36830 | 0.94410 | 0.14160 | 0.1290* | |
H1C | 0.51650 | 0.80190 | 0.15690 | 0.1290* | |
H3 | 0.57180 | 0.74160 | 0.40540 | 0.0760* | |
H4 | 0.47290 | 0.74260 | 0.65750 | 0.0680* | |
H6 | 0.07230 | 1.07450 | 0.61420 | 0.0670* | |
H7 | 0.17880 | 1.07680 | 0.36360 | 0.0790* | |
H9 | 0.24500 | 0.51800 | 0.71600 | 0.0730* | |
H10 | 0.07920 | 0.39670 | 0.62450 | 0.0800* | |
H12 | −0.31690 | 0.66430 | 0.89310 | 0.0720* | |
H13 | −0.15450 | 0.78950 | 0.98270 | 0.0680* | |
H14A | −0.27990 | 0.48930 | 0.61030 | 0.1050* | |
H14B | −0.33800 | 0.43100 | 0.77020 | 0.1050* | |
H14C | −0.18250 | 0.32780 | 0.66110 | 0.1050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0441 (3) | 0.0466 (3) | 0.0429 (2) | −0.0104 (2) | −0.0093 (2) | −0.0033 (2) |
O1 | 0.0451 (7) | 0.0608 (8) | 0.0641 (8) | −0.0050 (6) | −0.0149 (6) | −0.0001 (6) |
O2 | 0.0579 (8) | 0.0586 (8) | 0.0416 (6) | −0.0118 (6) | −0.0084 (5) | −0.0055 (6) |
N1 | 0.0467 (9) | 0.0452 (9) | 0.0461 (8) | −0.0127 (8) | −0.0018 (6) | −0.0058 (7) |
C1 | 0.0891 (17) | 0.131 (2) | 0.0475 (11) | −0.0617 (17) | 0.0057 (10) | −0.0124 (12) |
C2 | 0.0595 (13) | 0.0780 (14) | 0.0495 (10) | −0.0430 (11) | −0.0023 (9) | −0.0089 (10) |
C3 | 0.0528 (12) | 0.0689 (13) | 0.0619 (12) | −0.0190 (10) | 0.0074 (9) | −0.0175 (10) |
C4 | 0.0472 (11) | 0.0590 (12) | 0.0575 (11) | −0.0080 (9) | −0.0032 (8) | −0.0046 (9) |
C5 | 0.0404 (9) | 0.0443 (9) | 0.0449 (9) | −0.0197 (8) | −0.0036 (7) | −0.0069 (7) |
C6 | 0.0432 (10) | 0.0656 (12) | 0.0558 (11) | −0.0151 (9) | −0.0042 (8) | 0.0038 (9) |
C7 | 0.0588 (13) | 0.0898 (16) | 0.0566 (11) | −0.0317 (12) | −0.0141 (9) | 0.0142 (11) |
C8 | 0.0452 (10) | 0.0391 (9) | 0.0426 (8) | −0.0108 (7) | −0.0070 (7) | 0.0009 (7) |
C9 | 0.0454 (11) | 0.0571 (12) | 0.0748 (13) | −0.0116 (9) | −0.0022 (9) | −0.0200 (10) |
C10 | 0.0683 (14) | 0.0542 (12) | 0.0765 (14) | −0.0164 (11) | −0.0098 (11) | −0.0226 (10) |
C11 | 0.0611 (12) | 0.0487 (10) | 0.0549 (10) | −0.0222 (9) | −0.0189 (9) | 0.0085 (8) |
C12 | 0.0452 (11) | 0.0654 (13) | 0.0676 (12) | −0.0160 (10) | −0.0080 (9) | −0.0067 (10) |
C13 | 0.0465 (11) | 0.0610 (12) | 0.0581 (11) | −0.0120 (9) | −0.0032 (8) | −0.0160 (9) |
C14 | 0.0783 (15) | 0.0678 (14) | 0.0790 (14) | −0.0320 (12) | −0.0324 (12) | 0.0043 (11) |
S1—O1 | 1.4217 (14) | C11—C14 | 1.511 (3) |
S1—O2 | 1.4324 (12) | C11—C12 | 1.372 (2) |
S1—N1 | 1.6276 (16) | C12—C13 | 1.373 (3) |
S1—C8 | 1.7576 (18) | C1—H1A | 0.9600 |
N1—C5 | 1.429 (2) | C1—H1B | 0.9600 |
N1—H1 | 0.81 (3) | C1—H1C | 0.9600 |
C1—C2 | 1.504 (3) | C3—H3 | 0.9300 |
C2—C7 | 1.376 (4) | C4—H4 | 0.9300 |
C2—C3 | 1.368 (3) | C6—H6 | 0.9300 |
C3—C4 | 1.379 (3) | C7—H7 | 0.9300 |
C4—C5 | 1.376 (3) | C9—H9 | 0.9300 |
C5—C6 | 1.375 (2) | C10—H10 | 0.9300 |
C6—C7 | 1.379 (3) | C12—H12 | 0.9300 |
C8—C13 | 1.374 (3) | C13—H13 | 0.9300 |
C8—C9 | 1.373 (2) | C14—H14A | 0.9600 |
C9—C10 | 1.382 (3) | C14—H14B | 0.9600 |
C10—C11 | 1.374 (3) | C14—H14C | 0.9600 |
S1···H4 | 3.0400 | H1···O2i | 2.11 (3) |
O1···C4 | 3.049 (2) | H1A···N1iv | 2.8000 |
O2···N1i | 2.904 (2) | H1A···C5iv | 3.0100 |
O2···C14ii | 3.377 (3) | H1B···H7 | 2.4300 |
O1···H4 | 2.4500 | H1C···H3 | 2.4700 |
O1···H9 | 2.6100 | H3···H1C | 2.4700 |
O1···H12iii | 2.8900 | H3···H9vii | 2.5400 |
O2···H13 | 2.6100 | H4···S1 | 3.0400 |
O2···H1i | 2.11 (3) | H4···O1 | 2.4500 |
N1···O2i | 2.904 (2) | H6···H1 | 2.3000 |
N1···H1Aiv | 2.8000 | H6···C7v | 3.0400 |
C2···C4iv | 3.481 (3) | H7···H1B | 2.4300 |
C4···O1 | 3.049 (2) | H9···O1 | 2.6100 |
C4···C2iv | 3.481 (3) | H9···H3vii | 2.5400 |
C6···C6v | 3.595 (3) | H10···H14C | 2.4400 |
C6···C7v | 3.587 (3) | H12···O1viii | 2.8900 |
C7···C6v | 3.587 (3) | H12···H14B | 2.4500 |
C14···O2ii | 3.377 (3) | H13···O2 | 2.6100 |
C2···H14Cvi | 3.0800 | H14B···H12 | 2.4500 |
C5···H1Aiv | 3.0100 | H14C···H10 | 2.4400 |
C7···H6v | 3.0400 | H14C···C2vi | 3.0800 |
H1···H6 | 2.3000 | ||
O1—S1—O2 | 119.28 (8) | C2—C1—H1A | 109.00 |
O1—S1—N1 | 108.52 (9) | C2—C1—H1B | 110.00 |
O1—S1—C8 | 108.38 (8) | C2—C1—H1C | 109.00 |
O2—S1—N1 | 104.26 (8) | H1A—C1—H1B | 109.00 |
O2—S1—C8 | 108.41 (8) | H1A—C1—H1C | 109.00 |
N1—S1—C8 | 107.41 (8) | H1B—C1—H1C | 109.00 |
S1—N1—C5 | 123.93 (13) | C2—C3—H3 | 118.00 |
C5—N1—H1 | 112.3 (13) | C4—C3—H3 | 119.00 |
S1—N1—H1 | 114.3 (16) | C3—C4—H4 | 120.00 |
C1—C2—C7 | 121.5 (2) | C5—C4—H4 | 120.00 |
C1—C2—C3 | 121.5 (2) | C5—C6—H6 | 120.00 |
C3—C2—C7 | 117.01 (18) | C7—C6—H6 | 120.00 |
C2—C3—C4 | 122.9 (2) | C2—C7—H7 | 119.00 |
C3—C4—C5 | 119.16 (18) | C6—C7—H7 | 119.00 |
C4—C5—C6 | 119.03 (16) | C8—C9—H9 | 120.00 |
N1—C5—C6 | 118.64 (16) | C10—C9—H9 | 120.00 |
N1—C5—C4 | 122.18 (16) | C9—C10—H10 | 119.00 |
C5—C6—C7 | 120.51 (18) | C11—C10—H10 | 119.00 |
C2—C7—C6 | 121.4 (2) | C11—C12—H12 | 119.00 |
C9—C8—C13 | 119.86 (17) | C13—C12—H12 | 119.00 |
S1—C8—C9 | 119.76 (14) | C8—C13—H13 | 120.00 |
S1—C8—C13 | 120.37 (13) | C12—C13—H13 | 120.00 |
C8—C9—C10 | 119.12 (17) | C11—C14—H14A | 109.00 |
C9—C10—C11 | 121.65 (16) | C11—C14—H14B | 109.00 |
C10—C11—C14 | 121.20 (17) | C11—C14—H14C | 110.00 |
C10—C11—C12 | 118.13 (17) | H14A—C14—H14B | 109.00 |
C12—C11—C14 | 120.68 (17) | H14A—C14—H14C | 109.00 |
C11—C12—C13 | 121.15 (17) | H14B—C14—H14C | 109.00 |
C8—C13—C12 | 120.09 (16) | ||
O1—S1—N1—C5 | 56.26 (18) | C3—C4—C5—C6 | −1.4 (3) |
O2—S1—N1—C5 | −175.62 (16) | C3—C4—C5—N1 | −177.08 (19) |
C8—S1—N1—C5 | −60.71 (18) | C4—C5—C6—C7 | 0.3 (3) |
O1—S1—C8—C13 | 155.34 (14) | N1—C5—C6—C7 | 176.04 (19) |
O2—S1—C8—C13 | 24.51 (16) | C5—C6—C7—C2 | 1.3 (3) |
N1—S1—C8—C13 | −87.60 (15) | S1—C8—C9—C10 | −177.84 (13) |
O2—S1—C8—C9 | −156.51 (14) | C13—C8—C9—C10 | 1.2 (3) |
N1—S1—C8—C9 | 91.38 (15) | S1—C8—C13—C12 | 178.40 (14) |
O1—S1—C8—C9 | −25.69 (16) | C9—C8—C13—C12 | −0.6 (3) |
S1—N1—C5—C6 | 134.31 (16) | C8—C9—C10—C11 | −1.4 (3) |
S1—N1—C5—C4 | −50.0 (2) | C9—C10—C11—C12 | 1.0 (3) |
C3—C2—C7—C6 | −1.5 (4) | C9—C10—C11—C14 | −178.98 (17) |
C1—C2—C7—C6 | 179.9 (2) | C10—C11—C12—C13 | −0.5 (3) |
C7—C2—C3—C4 | 0.2 (4) | C14—C11—C12—C13 | 179.57 (17) |
C1—C2—C3—C4 | 178.9 (2) | C11—C12—C13—C8 | 0.2 (3) |
C2—C3—C4—C5 | 1.2 (4) |
Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x, −y+1, −z+2; (iii) x+1, y, z; (iv) −x+1, −y+2, −z+1; (v) −x, −y+2, −z+1; (vi) −x, −y+1, −z+1; (vii) −x+1, −y+1, −z+1; (viii) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.81 (3) | 2.11 (3) | 2.904 (2) | 170 (2) |
C4—H4···O1 | 0.93 | 2.45 | 3.049 (2) | 122 |
Symmetry code: (i) −x, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C14H15NO2S |
Mr | 261.34 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 8.6419 (8), 8.8016 (8), 9.2509 (7) |
α, β, γ (°) | 88.187 (4), 77.010 (4), 74.812 (4) |
V (Å3) | 661.41 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.28 × 0.17 × 0.08 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11831, 3259, 2323 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.122, 1.01 |
No. of reflections | 3259 |
No. of parameters | 169 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.24, −0.21 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.81 (3) | 2.11 (3) | 2.904 (2) | 170 (2) |
C4—H4···O1 | 0.93 | 2.45 | 3.049 (2) | 122 |
Symmetry code: (i) −x, −y+2, −z+2. |
Footnotes
‡Additional corresponding author, e-mail: iuklodhi@yahoo.com.
Acknowledgements
The authors are grateful to Mr Muhammad Hussain of Bana International for providing technical support to the Materials Chemistry Laboratory, Government College University.
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Sulfonamides are well known for their antibacterial and enzyme inhibitor properties (Pandya et al., 2003). Aromatic sulfonamides were also reported to inhibit the growth of tumor cells (Supuran & Scozzafava, 2000). In continuation of our studies (Sharif et al., 2010), herein, we report the crystal structure of the title compound.
The title molecule (I), (Fig. 1), is bent at the N atom with the C8—SO2—NH—C5 torsion angle of -60.71 (18)°. The dihedral angle between the two aromatic rings is 70.53 (10)°.
The molecular conformation of the title compound is stabilized by a weak intramolecular C—H···O hydrogen bond, generating an S(6) ring motif (Etter, 1990; Bernstein et al., 1995) (Table 1). In the crystal structure of the title compound, inversion-related molecules are linked into dimers by pairs of N—H···O hydrogen bonds, forming an R22(8) graph-set motif (Table 1 and Fig. 2).