organic compounds
2,4-Dimethyl-N-(3-methylphenyl)benzenesulfonamide
aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com
In the structure of the title compound, C15H17NO2S, the dihedral angle between the two aromatic rings is 47.1 (1)°. In the molecules are connected by N—H⋯O hydrogen bonds, forming C(4) chains running along the c axis.
Related literature
For the preparation of the title compound, see: Savitha & Gowda (2006). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2009, 2010); Nirmala et al. (2009). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536810011529/bt5222sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810011529/bt5222Isup2.hkl
The solution of 1,3-xylene (1,3-dimethylbenzene) (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0 ° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 2,4-dimethylbenzenesulfonylchloride was treated with m-toluidine in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid 2,4-dimethyl-N-(3-methylphenyl)benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra (Savitha & Gowda, 2006). The prism like colourless single crystals used in X-ray diffraction studies were grown in ethanolic solution by a slow evaporation at room temperature.
The H atom of the NH group was located in a difference map and its positional parameters were refined. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.96 Å. All H atoms were refined with isotropic displacement parameters set to 1.2 times of the Ueq of the parent atom.
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C15H17NO2S | F(000) = 584 |
Mr = 275.36 | Dx = 1.292 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3146 reflections |
a = 9.110 (1) Å | θ = 2.6–27.7° |
b = 15.367 (2) Å | µ = 0.23 mm−1 |
c = 10.422 (1) Å | T = 299 K |
β = 104.05 (1)° | Prism, colourless |
V = 1415.4 (3) Å3 | 0.40 × 0.40 × 0.26 mm |
Z = 4 |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 2870 independent reflections |
Radiation source: fine-focus sealed tube | 2375 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
Rotation method data acquisition using ω and phi scans | θmax = 26.4°, θmin = 2.7° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −11→9 |
Tmin = 0.915, Tmax = 0.944 | k = −19→14 |
5538 measured reflections | l = −13→10 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0485P)2 + 0.8232P] where P = (Fo2 + 2Fc2)/3 |
2870 reflections | (Δ/σ)max = 0.014 |
178 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C15H17NO2S | V = 1415.4 (3) Å3 |
Mr = 275.36 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.110 (1) Å | µ = 0.23 mm−1 |
b = 15.367 (2) Å | T = 299 K |
c = 10.422 (1) Å | 0.40 × 0.40 × 0.26 mm |
β = 104.05 (1)° |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 2870 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 2375 reflections with I > 2σ(I) |
Tmin = 0.915, Tmax = 0.944 | Rint = 0.012 |
5538 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.23 e Å−3 |
2870 reflections | Δρmin = −0.34 e Å−3 |
178 parameters |
Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4436 (2) | 0.60399 (12) | 0.09959 (19) | 0.0371 (4) | |
C2 | 0.4722 (2) | 0.55232 (13) | 0.2140 (2) | 0.0411 (4) | |
C3 | 0.3789 (2) | 0.48048 (14) | 0.2118 (2) | 0.0492 (5) | |
H3 | 0.3962 | 0.4450 | 0.2863 | 0.059* | |
C4 | 0.2619 (2) | 0.45894 (14) | 0.1049 (3) | 0.0522 (6) | |
C5 | 0.2385 (3) | 0.51066 (16) | −0.0060 (2) | 0.0567 (6) | |
H5 | 0.1616 | 0.4968 | −0.0797 | 0.068* | |
C6 | 0.3279 (2) | 0.58303 (15) | −0.0092 (2) | 0.0491 (5) | |
H6 | 0.3103 | 0.6177 | −0.0846 | 0.059* | |
C7 | 0.3096 (2) | 0.79578 (12) | 0.12108 (18) | 0.0361 (4) | |
C8 | 0.2602 (2) | 0.84940 (13) | 0.01270 (19) | 0.0415 (4) | |
H8 | 0.3302 | 0.8725 | −0.0298 | 0.050* | |
C9 | 0.1078 (2) | 0.86943 (14) | −0.0339 (2) | 0.0485 (5) | |
C10 | 0.0062 (3) | 0.83549 (16) | 0.0326 (3) | 0.0574 (6) | |
H10 | −0.0963 | 0.8480 | 0.0027 | 0.069* | |
C11 | 0.0547 (3) | 0.78367 (17) | 0.1417 (3) | 0.0579 (6) | |
H11 | −0.0150 | 0.7622 | 0.1858 | 0.069* | |
C12 | 0.2064 (2) | 0.76310 (15) | 0.1869 (2) | 0.0470 (5) | |
H12 | 0.2388 | 0.7277 | 0.2607 | 0.056* | |
C13 | 0.5968 (3) | 0.56894 (17) | 0.3359 (2) | 0.0578 (6) | |
H13A | 0.5926 | 0.6284 | 0.3629 | 0.069* | |
H13B | 0.6929 | 0.5578 | 0.3168 | 0.069* | |
H13C | 0.5841 | 0.5312 | 0.4058 | 0.069* | |
C14 | 0.1627 (3) | 0.38099 (18) | 0.1097 (3) | 0.0747 (8) | |
H14A | 0.1046 | 0.3909 | 0.1738 | 0.090* | |
H14B | 0.2248 | 0.3303 | 0.1341 | 0.090* | |
H14C | 0.0955 | 0.3722 | 0.0243 | 0.090* | |
C15 | 0.0547 (3) | 0.92755 (19) | −0.1527 (3) | 0.0722 (8) | |
H15A | 0.1317 | 0.9310 | −0.2010 | 0.087* | |
H15B | 0.0345 | 0.9847 | −0.1239 | 0.087* | |
H15C | −0.0361 | 0.9040 | −0.2087 | 0.087* | |
N1 | 0.46833 (19) | 0.77649 (11) | 0.16714 (16) | 0.0385 (4) | |
H1N | 0.499 (3) | 0.7705 (15) | 0.249 (2) | 0.046* | |
O1 | 0.69751 (16) | 0.69397 (11) | 0.16345 (16) | 0.0528 (4) | |
O2 | 0.51059 (18) | 0.72673 (10) | −0.04494 (14) | 0.0497 (4) | |
S1 | 0.54326 (5) | 0.70137 (3) | 0.09104 (5) | 0.03742 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0366 (9) | 0.0369 (10) | 0.0394 (10) | 0.0039 (8) | 0.0121 (8) | −0.0016 (8) |
C2 | 0.0402 (10) | 0.0411 (11) | 0.0437 (11) | 0.0093 (8) | 0.0132 (8) | 0.0034 (8) |
C3 | 0.0516 (12) | 0.0411 (11) | 0.0600 (13) | 0.0067 (9) | 0.0230 (10) | 0.0058 (10) |
C4 | 0.0462 (12) | 0.0414 (11) | 0.0754 (16) | −0.0002 (9) | 0.0270 (11) | −0.0091 (11) |
C5 | 0.0492 (13) | 0.0552 (14) | 0.0613 (14) | −0.0057 (11) | 0.0049 (10) | −0.0138 (11) |
C6 | 0.0516 (12) | 0.0511 (13) | 0.0411 (11) | 0.0000 (10) | 0.0044 (9) | −0.0020 (9) |
C7 | 0.0386 (10) | 0.0353 (10) | 0.0351 (9) | −0.0017 (8) | 0.0106 (7) | −0.0069 (8) |
C8 | 0.0456 (11) | 0.0397 (10) | 0.0417 (10) | −0.0010 (9) | 0.0154 (8) | −0.0017 (8) |
C9 | 0.0483 (12) | 0.0447 (12) | 0.0512 (12) | 0.0073 (9) | 0.0093 (9) | −0.0012 (9) |
C10 | 0.0404 (12) | 0.0573 (14) | 0.0746 (16) | 0.0049 (10) | 0.0141 (11) | −0.0018 (12) |
C11 | 0.0488 (13) | 0.0625 (15) | 0.0695 (15) | −0.0050 (11) | 0.0283 (11) | 0.0010 (12) |
C12 | 0.0501 (12) | 0.0504 (12) | 0.0434 (11) | −0.0025 (10) | 0.0167 (9) | 0.0015 (9) |
C13 | 0.0599 (14) | 0.0602 (14) | 0.0476 (13) | 0.0055 (12) | 0.0021 (10) | 0.0126 (11) |
C14 | 0.0625 (16) | 0.0534 (15) | 0.116 (2) | −0.0128 (12) | 0.0367 (16) | −0.0095 (15) |
C15 | 0.0686 (17) | 0.0737 (18) | 0.0720 (17) | 0.0219 (14) | 0.0124 (13) | 0.0188 (14) |
N1 | 0.0411 (9) | 0.0435 (9) | 0.0297 (8) | −0.0028 (7) | 0.0064 (7) | −0.0042 (7) |
O1 | 0.0348 (8) | 0.0641 (10) | 0.0587 (9) | −0.0024 (7) | 0.0101 (7) | 0.0024 (8) |
O2 | 0.0614 (9) | 0.0565 (9) | 0.0359 (7) | −0.0010 (7) | 0.0207 (7) | 0.0015 (7) |
S1 | 0.0361 (3) | 0.0441 (3) | 0.0336 (3) | −0.0008 (2) | 0.01146 (18) | 0.0008 (2) |
C1—C6 | 1.386 (3) | C10—C11 | 1.371 (4) |
C1—C2 | 1.403 (3) | C10—H10 | 0.9300 |
C1—S1 | 1.764 (2) | C11—C12 | 1.385 (3) |
C2—C3 | 1.390 (3) | C11—H11 | 0.9300 |
C2—C13 | 1.506 (3) | C12—H12 | 0.9300 |
C3—C4 | 1.383 (3) | C13—H13A | 0.9600 |
C3—H3 | 0.9300 | C13—H13B | 0.9600 |
C4—C5 | 1.376 (3) | C13—H13C | 0.9600 |
C4—C14 | 1.509 (3) | C14—H14A | 0.9600 |
C5—C6 | 1.383 (3) | C14—H14B | 0.9600 |
C5—H5 | 0.9300 | C14—H14C | 0.9600 |
C6—H6 | 0.9300 | C15—H15A | 0.9600 |
C7—C8 | 1.382 (3) | C15—H15B | 0.9600 |
C7—C12 | 1.386 (3) | C15—H15C | 0.9600 |
C7—N1 | 1.439 (2) | N1—S1 | 1.6402 (17) |
C8—C9 | 1.390 (3) | N1—H1N | 0.83 (2) |
C8—H8 | 0.9300 | O1—S1 | 1.4291 (15) |
C9—C10 | 1.385 (3) | O2—S1 | 1.4298 (15) |
C9—C15 | 1.508 (3) | ||
C6—C1—C2 | 120.74 (19) | C12—C11—H11 | 119.7 |
C6—C1—S1 | 117.03 (16) | C11—C12—C7 | 119.4 (2) |
C2—C1—S1 | 122.10 (15) | C11—C12—H12 | 120.3 |
C3—C2—C1 | 116.67 (19) | C7—C12—H12 | 120.3 |
C3—C2—C13 | 118.75 (19) | C2—C13—H13A | 109.5 |
C1—C2—C13 | 124.57 (19) | C2—C13—H13B | 109.5 |
C4—C3—C2 | 123.5 (2) | H13A—C13—H13B | 109.5 |
C4—C3—H3 | 118.2 | C2—C13—H13C | 109.5 |
C2—C3—H3 | 118.2 | H13A—C13—H13C | 109.5 |
C5—C4—C3 | 118.1 (2) | H13B—C13—H13C | 109.5 |
C5—C4—C14 | 121.0 (2) | C4—C14—H14A | 109.5 |
C3—C4—C14 | 120.9 (2) | C4—C14—H14B | 109.5 |
C4—C5—C6 | 120.8 (2) | H14A—C14—H14B | 109.5 |
C4—C5—H5 | 119.6 | C4—C14—H14C | 109.5 |
C6—C5—H5 | 119.6 | H14A—C14—H14C | 109.5 |
C5—C6—C1 | 120.1 (2) | H14B—C14—H14C | 109.5 |
C5—C6—H6 | 119.9 | C9—C15—H15A | 109.5 |
C1—C6—H6 | 119.9 | C9—C15—H15B | 109.5 |
C8—C7—C12 | 119.67 (19) | H15A—C15—H15B | 109.5 |
C8—C7—N1 | 119.79 (17) | C9—C15—H15C | 109.5 |
C12—C7—N1 | 120.51 (18) | H15A—C15—H15C | 109.5 |
C7—C8—C9 | 121.15 (19) | H15B—C15—H15C | 109.5 |
C7—C8—H8 | 119.4 | C7—N1—S1 | 119.08 (13) |
C9—C8—H8 | 119.4 | C7—N1—H1N | 115.2 (16) |
C10—C9—C8 | 118.3 (2) | S1—N1—H1N | 109.8 (16) |
C10—C9—C15 | 120.9 (2) | O1—S1—O2 | 119.10 (9) |
C8—C9—C15 | 120.8 (2) | O1—S1—N1 | 105.78 (9) |
C11—C10—C9 | 120.9 (2) | O2—S1—N1 | 106.05 (9) |
C11—C10—H10 | 119.5 | O1—S1—C1 | 110.99 (9) |
C9—C10—H10 | 119.5 | O2—S1—C1 | 107.19 (9) |
C10—C11—C12 | 120.6 (2) | N1—S1—C1 | 107.04 (9) |
C10—C11—H11 | 119.7 | ||
C6—C1—C2—C3 | −0.2 (3) | C8—C9—C10—C11 | 0.2 (4) |
S1—C1—C2—C3 | 175.52 (14) | C15—C9—C10—C11 | −179.0 (2) |
C6—C1—C2—C13 | 178.9 (2) | C9—C10—C11—C12 | −0.9 (4) |
S1—C1—C2—C13 | −5.4 (3) | C10—C11—C12—C7 | 0.3 (4) |
C1—C2—C3—C4 | −0.5 (3) | C8—C7—C12—C11 | 1.0 (3) |
C13—C2—C3—C4 | −179.7 (2) | N1—C7—C12—C11 | 179.05 (19) |
C2—C3—C4—C5 | 1.2 (3) | C8—C7—N1—S1 | −80.5 (2) |
C2—C3—C4—C14 | −178.8 (2) | C12—C7—N1—S1 | 101.5 (2) |
C3—C4—C5—C6 | −1.2 (3) | C7—N1—S1—O1 | −176.76 (14) |
C14—C4—C5—C6 | 178.8 (2) | C7—N1—S1—O2 | 55.85 (17) |
C4—C5—C6—C1 | 0.5 (4) | C7—N1—S1—C1 | −58.35 (17) |
C2—C1—C6—C5 | 0.2 (3) | C6—C1—S1—O1 | −148.09 (16) |
S1—C1—C6—C5 | −175.76 (17) | C2—C1—S1—O1 | 36.00 (19) |
C12—C7—C8—C9 | −1.7 (3) | C6—C1—S1—O2 | −16.48 (19) |
N1—C7—C8—C9 | −179.83 (18) | C2—C1—S1—O2 | 167.61 (15) |
C7—C8—C9—C10 | 1.1 (3) | C6—C1—S1—N1 | 96.94 (17) |
C7—C8—C9—C15 | −179.6 (2) | C2—C1—S1—N1 | −78.97 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.83 (2) | 2.13 (3) | 2.932 (2) | 162 (2) |
Symmetry code: (i) x, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H17NO2S |
Mr | 275.36 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 299 |
a, b, c (Å) | 9.110 (1), 15.367 (2), 10.422 (1) |
β (°) | 104.05 (1) |
V (Å3) | 1415.4 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.40 × 0.40 × 0.26 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.915, 0.944 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5538, 2870, 2375 |
Rint | 0.012 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.112, 1.06 |
No. of reflections | 2870 |
No. of parameters | 178 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.34 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.83 (2) | 2.13 (3) | 2.932 (2) | 162 (2) |
Symmetry code: (i) x, −y+3/2, z+1/2. |
References
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As part of a study of the effect of substitutions on the structures of N-(aryl)-arylsulfonamides (Gowda et al., 2009; Gowda et al., 2010; Nirmala et al., 2009), in the present work, the structure of 2,4-dimethyl-N-(3-methylphenyl)benzenesulfonamide (I) has been determined (Fig. 1). The conformation of the N—C bond in the C—SO2—NH—C segment has gauche torsions with respect to the S═O bonds. The molecule is twisted at the S—N bond with the C1—SO2—NH—C7 torsion angle of -58.4 (2)°, compared to the values of 71.6 (1)° in 2,4-dimethyl-N-(3-methylphenyl)benzenesulfonamide (II)(Nirmala et al., 2009), -46.1 (3)° (molecule 1) & 47.7 (3)° (molecule 2) in the two molecules of 2,4-dimethyl-N-(phenyl)- benzenesulfonamide (III)(Gowda et al., 2009) and 55.8 (2)° and -58.4 (3)°, respectively, in the 2 molecules of N- (3-methylphenyl)benzenesulfonamide (IV)(Gowda et al., 2010). The conformation of the N—H bond in (I) is anti to the 3-methyl group in the aniline benzene ring, compared the syn conformation observed between the N—H bond and the 3-methyl group in (IV).
The sulfonyl benzene and the aniline benzene rings in (I) are tilted relative to each other by 47.1 (1)°, compared to the values of 47.0 (1)° in (II), 67.5 (1)° in molecule 1 and 72.9 (1)° in molecule 2 of (III), and 67.9 (1)° in molecule 1 and 68.6 (1)° in molecule 2 of (IV).
The other bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The crystal packing shows that the molecules are connected by N—H···O hydrogen bonds (Table 1) to chains running along the c axis (Fig. 2).