2,4-Dimethyl-N-(2-methyl­phen­yl)benzene­sulfonamide

Nirmala, P.G.; Gowda, B.T.; Foro, S.; Fuess, H.

doi:10.1107/S1600536809049563

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3210

doi:10.1107/S1600536809049563

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2,4-Dimethyl-N-(2-methylphenyl)benzenesulfonamide

P. G. Nirmala,^a B. Thimme Gowda,^a ^* Sabine Foro ^b and Hartmut Fuess ^b

^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

(Received 19 November 2009; accepted 19 November 2009; online 25 November 2009)

In the title compound, C₁₅H₁₇NO₂S, the molecule is bent at the S atom with a C—SO₂—NH—C torsion angle of 71.6 (1)°. The two benzene rings are tilted by 47.0 (1)° relative to each other. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ). For related structures, see: Gelbrich et al. (2007 ); Gowda et al. (2008 ; 2009a ,b ); Perlovich et al. (2006 ).

Experimental

Crystal data

C₁₅H₁₇NO₂S
M_r = 275.36
Triclinic, $[P \overline 1]$
a = 8.1789 (8) Å
b = 8.2659 (9) Å
c = 11.005 (1) Å
α = 96.249 (9)°
β = 96.078 (9)°
γ = 106.782 (9)°
V = 700.68 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 299 K
0.48 × 0.26 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.898, T_max = 0.973
4894 measured reflections
2862 independent reflections
2446 reflections with I > 2σ(I)
R_int = 0.010

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.116
S = 1.05
2862 reflections
178 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.83 (2)	2.19 (2)	3.002 (2)	165 (2)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049563/ci2971sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049563/ci2971Isup2.hkl

checkCIF report

Comment top

As part of a study of the substituent effects on the structures of N-(aryl)-arylsulfonamides (Gowda et al., 2008; 2009a,b), in the present work, the structure of 2,4-dimethyl-N-(2-methylphenyl)benzenesulfonamide (I) has been determined (Fig. 1). The molecule is bent at the S atom with the C—SO₂—NH—C torsion angle of 71.6 (1)°, compared with the values of 73.0 (2)° in 4-chloro-2-methyl-N-(2-methylphenyl)benzenesulfonamide (II) (Gowda et al. 2009b), -46.1 (3)° (molecule 1) and 47.7 (3)° (molecule 2) in the two molecules of 2,4-dimethyl-N-(phenyl)benzenesulfonamide (III) (Gowda et al. 2009a) and 72.0 (2)° in N-(2-methylphenyl)benzenesulfonamide (IV) (Gowda et al., 2008). The two benzene rings in (I) are tilted relative to each other by 47.0 (1)°, compared to the values of 45.8 (1)° in (II), 67.5 (1)° in molecule 1 and 72.9 (1)° in molecule 2 of (III), and 61.5 (1)° in (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 of molecules in (I) is characterized by N—H···O hydrogen bonds (Table 1, Fig.2).

Related literature top

For the preparation of the title compound, see: Savitha & Gowda (2006). For related structures, see: Gelbrich et al. (2007); Gowda et al. (2008; 2009a,b); Perlovich et al. (2006).

Experimental top

A 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 o-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-(2-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.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: 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).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

2,4-Dimethyl-N-(2-methylphenyl)benzenesulfonamide top

Crystal data top

C₁₅H₁₇NO₂S	Z = 2
M_r = 275.36	F(000) = 292
Triclinic, P1	D_x = 1.305 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1789 (8) Å	Cell parameters from 2978 reflections
b = 8.2659 (9) Å	θ = 3.0–27.9°
c = 11.005 (1) Å	µ = 0.23 mm⁻¹
α = 96.249 (9)°	T = 299 K
β = 96.078 (9)°	Prism, colourless
γ = 106.782 (9)°	0.48 × 0.26 × 0.12 mm
V = 700.68 (12) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2862 independent reflections
Radiation source: fine-focus sealed tube	2446 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.010
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→10
T_min = 0.898, T_max = 0.973	k = −10→7
4894 measured reflections	l = −13→13

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.064P)² + 0.2128P] where P = (F_o² + 2F_c²)/3
2862 reflections	(Δ/σ)_max = 0.001
178 parameters	Δρ_max = 0.39 e Å⁻³
1 restraint	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₅H₁₇NO₂S	γ = 106.782 (9)°
M_r = 275.36	V = 700.68 (12) Å³
Triclinic, P1	Z = 2
a = 8.1789 (8) Å	Mo Kα radiation
b = 8.2659 (9) Å	µ = 0.23 mm⁻¹
c = 11.005 (1) Å	T = 299 K
α = 96.249 (9)°	0.48 × 0.26 × 0.12 mm
β = 96.078 (9)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2862 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2446 reflections with I > 2σ(I)
T_min = 0.898, T_max = 0.973	R_int = 0.010
4894 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.39 e Å⁻³
2862 reflections	Δρ_min = −0.24 e Å⁻³
178 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.1125 (2)	0.5794 (2)	0.78239 (16)	0.0390 (4)
C2	0.2116 (2)	0.6728 (2)	0.89249 (16)	0.0440 (4)
C3	0.1243 (3)	0.7397 (3)	0.97740 (17)	0.0496 (4)
H3	0.1876	0.8030	1.0513	0.060*
C4	−0.0514 (3)	0.7168 (2)	0.95762 (18)	0.0480 (4)
C5	−0.1451 (2)	0.6234 (3)	0.84761 (18)	0.0505 (4)
H5	−0.2633	0.6063	0.8322	0.061*
C6	−0.0645 (2)	0.5551 (2)	0.76046 (17)	0.0458 (4)
H6	−0.1287	0.4925	0.6866	0.055*
C7	0.4102 (2)	0.7886 (2)	0.61387 (14)	0.0380 (4)
C8	0.3900 (2)	0.9481 (2)	0.64940 (15)	0.0432 (4)
C9	0.5397 (3)	1.0860 (3)	0.68291 (19)	0.0599 (5)
H9	0.5304	1.1944	0.7053	0.072*
C10	0.7000 (3)	1.0659 (3)	0.6837 (2)	0.0693 (7)
H10	0.7978	1.1600	0.7075	0.083*
C11	0.7175 (3)	0.9075 (3)	0.6495 (2)	0.0691 (7)
H11	0.8268	0.8942	0.6511	0.083*
C12	0.5722 (2)	0.7676 (3)	0.61251 (19)	0.0525 (5)
H12	0.5831	0.6607	0.5870	0.063*
C13	0.4036 (3)	0.7076 (3)	0.9262 (2)	0.0642 (6)
H13A	0.4627	0.7664	0.8654	0.077*
H13B	0.4287	0.6014	0.9290	0.077*
H13C	0.4416	0.7771	1.0057	0.077*
C14	−0.1363 (3)	0.7946 (3)	1.0542 (2)	0.0660 (6)
H14A	−0.0497	0.8623	1.1206	0.079*
H14B	−0.2169	0.7053	1.0855	0.079*
H14C	−0.1960	0.8657	1.0176	0.079*
C15	0.2154 (3)	0.9733 (2)	0.6503 (2)	0.0583 (5)
H15A	0.1600	0.9167	0.7135	0.070*
H15B	0.1462	0.9261	0.5714	0.070*
H15C	0.2283	1.0932	0.6667	0.070*
N1	0.26247 (19)	0.64126 (19)	0.57272 (13)	0.0409 (3)
H1N	0.175 (2)	0.659 (3)	0.5378 (18)	0.049*
O1	0.06289 (17)	0.36111 (16)	0.58290 (13)	0.0527 (3)
O2	0.35102 (17)	0.45144 (17)	0.70879 (13)	0.0524 (3)
S1	0.20156 (5)	0.49271 (5)	0.65960 (4)	0.04048 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0394 (9)	0.0368 (8)	0.0420 (9)	0.0129 (7)	0.0056 (7)	0.0065 (7)
C2	0.0413 (9)	0.0472 (9)	0.0434 (9)	0.0139 (8)	0.0035 (7)	0.0074 (7)
C3	0.0527 (11)	0.0531 (11)	0.0422 (9)	0.0177 (9)	0.0034 (8)	0.0025 (8)
C4	0.0538 (11)	0.0481 (10)	0.0500 (10)	0.0232 (9)	0.0146 (8)	0.0127 (8)
C5	0.0404 (9)	0.0584 (11)	0.0571 (11)	0.0200 (9)	0.0087 (8)	0.0123 (9)
C6	0.0412 (9)	0.0480 (10)	0.0473 (10)	0.0143 (8)	0.0020 (7)	0.0051 (8)
C7	0.0374 (8)	0.0422 (9)	0.0328 (8)	0.0095 (7)	0.0055 (6)	0.0050 (6)
C8	0.0522 (10)	0.0408 (9)	0.0344 (8)	0.0100 (8)	0.0084 (7)	0.0046 (7)
C9	0.0737 (14)	0.0435 (10)	0.0498 (11)	0.0012 (10)	0.0025 (10)	0.0043 (8)
C10	0.0565 (13)	0.0683 (14)	0.0624 (13)	−0.0109 (11)	−0.0078 (10)	0.0199 (11)
C11	0.0368 (10)	0.0928 (18)	0.0765 (15)	0.0099 (11)	0.0044 (10)	0.0380 (13)
C12	0.0426 (10)	0.0627 (12)	0.0579 (11)	0.0201 (9)	0.0117 (8)	0.0176 (9)
C13	0.0440 (11)	0.0873 (16)	0.0544 (12)	0.0194 (11)	−0.0049 (9)	−0.0059 (11)
C14	0.0683 (14)	0.0747 (15)	0.0644 (13)	0.0333 (12)	0.0219 (11)	0.0065 (11)
C15	0.0692 (13)	0.0461 (11)	0.0683 (13)	0.0261 (10)	0.0246 (11)	0.0074 (9)
N1	0.0391 (8)	0.0405 (8)	0.0409 (8)	0.0117 (6)	0.0020 (6)	0.0006 (6)
O1	0.0516 (7)	0.0371 (6)	0.0622 (8)	0.0085 (6)	0.0031 (6)	−0.0050 (6)
O2	0.0499 (7)	0.0472 (7)	0.0660 (8)	0.0246 (6)	0.0075 (6)	0.0078 (6)
S1	0.0399 (2)	0.0329 (2)	0.0477 (3)	0.01217 (17)	0.00452 (18)	0.00091 (17)

Geometric parameters (Å, º) top

C1—C6	1.394 (2)	C10—C11	1.375 (4)
C1—C2	1.396 (2)	C10—H10	0.93
C1—S1	1.7799 (17)	C11—C12	1.384 (3)
C2—C3	1.394 (3)	C11—H11	0.93
C2—C13	1.510 (2)	C12—H12	0.93
C3—C4	1.385 (3)	C13—H13A	0.96
C3—H3	0.93	C13—H13B	0.96
C4—C5	1.381 (3)	C13—H13C	0.96
C4—C14	1.513 (3)	C14—H14A	0.96
C5—C6	1.380 (3)	C14—H14B	0.96
C5—H5	0.93	C14—H14C	0.96
C6—H6	0.93	C15—H15A	0.96
C7—C12	1.386 (2)	C15—H15B	0.96
C7—C8	1.395 (2)	C15—H15C	0.96
C7—N1	1.436 (2)	N1—S1	1.6350 (16)
C8—C9	1.393 (3)	N1—H1N	0.832 (15)
C8—C15	1.503 (3)	O1—S1	1.4377 (13)
C9—C10	1.368 (3)	O2—S1	1.4299 (13)
C9—H9	0.93

C6—C1—C2	120.83 (16)	C12—C11—H11	120.1
C6—C1—S1	115.77 (13)	C11—C12—C7	119.3 (2)
C2—C1—S1	123.34 (13)	C11—C12—H12	120.3
C3—C2—C1	116.59 (16)	C7—C12—H12	120.3
C3—C2—C13	117.89 (17)	C2—C13—H13A	109.5
C1—C2—C13	125.51 (17)	C2—C13—H13B	109.5
C4—C3—C2	123.53 (18)	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	118.18 (17)	H13B—C13—H13C	109.5
C5—C4—C14	121.52 (18)	C4—C14—H14A	109.5
C3—C4—C14	120.30 (19)	C4—C14—H14B	109.5
C6—C5—C4	120.45 (17)	H14A—C14—H14B	109.5
C6—C5—H5	119.8	C4—C14—H14C	109.5
C4—C5—H5	119.8	H14A—C14—H14C	109.5
C5—C6—C1	120.42 (17)	H14B—C14—H14C	109.5
C5—C6—H6	119.8	C8—C15—H15A	109.5
C1—C6—H6	119.8	C8—C15—H15B	109.5
C12—C7—C8	121.51 (17)	H15A—C15—H15B	109.5
C12—C7—N1	117.73 (16)	C8—C15—H15C	109.5
C8—C7—N1	120.71 (15)	H15A—C15—H15C	109.5
C9—C8—C7	117.21 (18)	H15B—C15—H15C	109.5
C9—C8—C15	120.60 (18)	C7—N1—S1	121.46 (11)
C7—C8—C15	122.19 (16)	C7—N1—H1N	116.5 (14)
C10—C9—C8	121.6 (2)	S1—N1—H1N	108.7 (15)
C10—C9—H9	119.2	O2—S1—O1	118.89 (8)
C8—C9—H9	119.2	O2—S1—N1	108.05 (8)
C9—C10—C11	120.4 (2)	O1—S1—N1	104.94 (8)
C9—C10—H10	119.8	O2—S1—C1	109.57 (8)
C11—C10—H10	119.8	O1—S1—C1	107.40 (8)
C10—C11—C12	119.9 (2)	N1—S1—C1	107.42 (8)
C10—C11—H11	120.1

C6—C1—C2—C3	−0.2 (3)	C15—C8—C9—C10	179.47 (19)
S1—C1—C2—C3	176.86 (13)	C8—C9—C10—C11	0.9 (3)
C6—C1—C2—C13	−179.88 (19)	C9—C10—C11—C12	0.8 (4)
S1—C1—C2—C13	−2.8 (3)	C10—C11—C12—C7	−1.8 (3)
C1—C2—C3—C4	0.4 (3)	C8—C7—C12—C11	1.2 (3)
C13—C2—C3—C4	−179.95 (19)	N1—C7—C12—C11	178.85 (17)
C2—C3—C4—C5	−0.3 (3)	C12—C7—N1—S1	75.97 (18)
C2—C3—C4—C14	−179.61 (19)	C8—C7—N1—S1	−106.39 (17)
C3—C4—C5—C6	0.0 (3)	C7—N1—S1—O2	−46.56 (15)
C14—C4—C5—C6	179.35 (18)	C7—N1—S1—O1	−174.35 (12)
C4—C5—C6—C1	0.1 (3)	C7—N1—S1—C1	71.57 (14)
C2—C1—C6—C5	0.0 (3)	C6—C1—S1—O2	−152.26 (13)
S1—C1—C6—C5	−177.30 (14)	C2—C1—S1—O2	30.51 (17)
C12—C7—C8—C9	0.3 (3)	C6—C1—S1—O1	−21.81 (16)
N1—C7—C8—C9	−177.20 (15)	C2—C1—S1—O1	160.95 (14)
C12—C7—C8—C15	179.46 (17)	C6—C1—S1—N1	90.60 (14)
N1—C7—C8—C15	1.9 (3)	C2—C1—S1—N1	−86.63 (16)
C7—C8—C9—C10	−1.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.83 (2)	2.19 (2)	3.002 (2)	165 (2)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇NO₂S
M_r	275.36
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	8.1789 (8), 8.2659 (9), 11.005 (1)
α, β, γ (°)	96.249 (9), 96.078 (9), 106.782 (9)
V (Å³)	700.68 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.48 × 0.26 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.898, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	4894, 2862, 2446
R_int	0.010
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.116, 1.05
No. of reflections	2862
No. of parameters	178
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.24

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.83 (2)	2.19 (2)	3.002 (2)	165 (2)

Symmetry code: (i) −x, −y+1, −z+1.

References

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Volume 65| Part 12| December 2009| Page o3210

doi:10.1107/S1600536809049563

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