N-(2,3-Dimethyl­phen­yl)-4-methyl-N-(4-methyl­phenyl­sulfon­yl)benzene­sulfonamide

Mughal, S.Y.; Khan, I.U.; Harrison, W.T.A.; Khan, M.H.; Tahir, M.N.

doi:10.1107/S1600536812039773

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o3013

https://doi.org/10.1107/S1600536812039773

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N-(2,3-Dimethylphenyl)-4-methyl-N-(4-methylphenylsulfonyl)benzenesulfonamide

Shumaila Younas Mughal,^a Islam Ullah Khan,^a ^* William T. A. Harrison,^b Muneeb Hayat Khan ^c and Muhammad Nawaz Tahir ^d

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, ^cQuestioned Documents Unit, Punjab Forensic Science Agency, Home Department, Lahore, Pakistan, and ^dDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: koolmuneeb@yahoo.com

(Received 13 September 2012; accepted 19 September 2012; online 26 September 2012)

In the title compound, C₂₂H₂₃NO₄S₂, the dihedral angles between the dimethylphenyl ring and the two methylphenyl rings are 41.19 (15) and 20.50 (17)°; the dihedral angle between the methylphenyl rings is 48.11 (14)°. The C—N—S—C torsion angles are −87.6 (2) and 77.43 (18)°. The only possible directional interactions in the crystal are very weak C—H⋯π interactions and very weak π–π stacking between parallel methylphenyl rings [centroid-to-centroid separation = 4.010 (2) Å and slippage = 1.987 Å].

Related literature

For a related structure, see: Mughal et al. (2012 ).

Experimental

Crystal data

C₂₂H₂₃NO₄S₂
M_r = 429.53
Triclinic, $[P \overline 1]$
a = 7.5523 (8) Å
b = 8.4635 (9) Å
c = 17.5004 (17) Å
α = 103.282 (7)°
β = 91.659 (7)°
γ = 108.382 (7)°
V = 1026.89 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 296 K
0.32 × 0.23 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.913, T_max = 0.966
16232 measured reflections
4569 independent reflections
2359 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.129
S = 0.96
4569 reflections
266 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C16–C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯Cgⁱ	0.96	2.96	3.912 (4)	169
Symmetry code: (i) 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: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812039773/xu5622sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039773/xu5622Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812039773/xu5622Isup3.cml

checkCIF report

Comment top

Rather than the intended product of 4-methyl-N-(2,3-dimethylphenyl)benzenesulfonamide, the title `double' sulfonamide (in which both amine N—N bonds have been replaced by N—S bonds), (I), (Fig. 1) was unexpectedly prepared. A similar double sulfonamide and previous related structures are described by Mughal et al. (2012).

The molecule of (I) cannot possess any local symmetry due to the two methyl groups of the xylene ring. If these are neglected, the rest of the molecule possesses approximate local twofold symmetry about the C1—N1 axis. The dihedral angles between the o-xylene ring (C1–C6) and the C9–C14 and C15–C20 toluyl rings are 41.19 (15) and 20.50 (17)°, respectively; the dihedral angle between the toluyl rings is 48.11 (14)°. The sulfonamide torsion angles in (I) are -87.6 (2)(2)° for C1—N1—S1—C9 and 77.43 (18)° for C1—N1—S2—C16. The bond-angle sum for N1 in (I) of 359.4° implies sp² hybridization for the N atom. However, its (presumed) unhybridized p orbital is almost orthogonal to the aromatic π system of the C1–C6 ring and the C1—N1 bond length of 1.452 (3) Å is that expected for a C—N single bond.

The only direction interactions in the crystal of (I) are a possible very weak C—H···π bond (Table 1) and aromatic π–π stacking between inversion-related pairs of C9–C14 rings [centroid–centroid separation = 4.010 (2) Å; slippage = 1.987 Å].

Related literature top

For a related structure, see: Mughal et al. (2012).

Experimental top

0.10 g of 2,3-dimethyl aniline was dissolved in 15 ml dichloromethane and 0.157 g of toulene sulfonyl chloride was added. The mixture was stirred at room temperature overnight and the pH was maintained at 8–9 with triethylamine. On completion of the reaction (after TLC), 1 M HCl solution was added and the organic layer was separated and allowed to evaporate at room temperature to generate light-brown crystals in 97% yield. Yellow blocks were recrystallized from ethanol solution.

Structure description top

For a related structure, see: Mughal et al. (2012).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: 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 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 50% probability level.

N-(2,3-Dimethylphenyl)-4-methyl-N-(4- methylphenylsulfonyl)benzenesulfonamide top

Crystal data top

C₂₂H₂₃NO₄S₂	Z = 2
M_r = 429.53	F(000) = 452
Triclinic, P1	D_x = 1.389 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5523 (8) Å	Cell parameters from 185 reflections
b = 8.4635 (9) Å	θ = 3.3–19.5°
c = 17.5004 (17) Å	µ = 0.29 mm⁻¹
α = 103.282 (7)°	T = 296 K
β = 91.659 (7)°	Block, yellow
γ = 108.382 (7)°	0.32 × 0.23 × 0.12 mm
V = 1026.89 (18) Å³

Data collection top

Bruker APEXII CCD diffractometer	4569 independent reflections
Radiation source: fine-focus sealed tube	2359 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ω scans	θ_max = 27.3°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→9
T_min = 0.913, T_max = 0.966	k = −10→10
16232 measured reflections	l = −22→22

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.052P)²] where P = (F_o² + 2F_c²)/3
4569 reflections	(Δ/σ)_max = 0.002
266 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₂H₂₃NO₄S₂	γ = 108.382 (7)°
M_r = 429.53	V = 1026.89 (18) Å³
Triclinic, P1	Z = 2
a = 7.5523 (8) Å	Mo Kα radiation
b = 8.4635 (9) Å	µ = 0.29 mm⁻¹
c = 17.5004 (17) Å	T = 296 K
α = 103.282 (7)°	0.32 × 0.23 × 0.12 mm
β = 91.659 (7)°

Data collection top

Bruker APEXII CCD diffractometer	4569 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2359 reflections with I > 2σ(I)
T_min = 0.913, T_max = 0.966	R_int = 0.068
16232 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 0.96	Δρ_max = 0.24 e Å⁻³
4569 reflections	Δρ_min = −0.30 e Å⁻³
266 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	0.1812 (4)	0.1458 (4)	0.21323 (18)	0.0419 (8)
C2	0.1984 (4)	−0.0039 (4)	0.22706 (18)	0.0439 (8)
C3	0.2906 (4)	−0.0938 (4)	0.17351 (19)	0.0462 (8)
C4	0.3599 (5)	−0.0318 (4)	0.1105 (2)	0.0569 (9)
H4	0.4194	−0.0923	0.0751	0.068*
C5	0.3422 (5)	0.1202 (5)	0.0990 (2)	0.0580 (10)
H5	0.3914	0.1611	0.0565	0.070*
C6	0.2535 (5)	0.2086 (4)	0.14952 (18)	0.0477 (8)
H6	0.2410	0.3099	0.1418	0.057*
C7	0.1242 (5)	−0.0688 (4)	0.29584 (18)	0.0546 (9)
H7A	0.0585	0.0028	0.3239	0.082*
H7B	0.2266	−0.0663	0.3305	0.082*
H7C	0.0398	−0.1848	0.2776	0.082*
C8	0.3123 (5)	−0.2576 (4)	0.1842 (2)	0.0694 (11)
H8A	0.3848	−0.2974	0.1447	0.104*
H8B	0.1906	−0.3432	0.1789	0.104*
H8C	0.3753	−0.2372	0.2357	0.104*
C9	0.2566 (4)	0.3436 (4)	0.41450 (18)	0.0433 (8)
C10	0.1242 (5)	0.3167 (4)	0.46751 (19)	0.0514 (9)
H10	0.0154	0.3442	0.4620	0.062*
C11	0.1568 (5)	0.2491 (4)	0.52790 (19)	0.0570 (9)
H11	0.0679	0.2307	0.5635	0.068*
C12	0.3164 (5)	0.2071 (4)	0.53832 (19)	0.0500 (9)
C13	0.4476 (5)	0.2369 (4)	0.48554 (19)	0.0533 (9)
H13	0.5568	0.2104	0.4918	0.064*
C14	0.4203 (5)	0.3057 (4)	0.42331 (18)	0.0468 (8)
H14	0.5100	0.3259	0.3882	0.056*
C15	0.3467 (5)	0.1285 (4)	0.6041 (2)	0.0719 (11)
H15A	0.3366	0.2009	0.6536	0.108*
H15B	0.4694	0.1175	0.6046	0.108*
H15C	0.2535	0.0169	0.5961	0.108*
C16	−0.1829 (4)	0.3224 (4)	0.18865 (18)	0.0419 (8)
C17	−0.1586 (4)	0.2853 (4)	0.10925 (19)	0.0483 (8)
H17	−0.1287	0.1878	0.0862	0.058*
C18	−0.1790 (4)	0.3935 (4)	0.06515 (19)	0.0504 (9)
H18	−0.1608	0.3694	0.0119	0.061*
C19	−0.2260 (4)	0.5380 (4)	0.09775 (19)	0.0487 (8)
C20	−0.2563 (4)	0.5687 (4)	0.17601 (19)	0.0507 (9)
H20	−0.2927	0.6628	0.1984	0.061*
C21	−0.2338 (4)	0.4631 (4)	0.22206 (19)	0.0451 (8)
H21	−0.2528	0.4867	0.2752	0.054*
C22	−0.2436 (5)	0.6588 (4)	0.0491 (2)	0.0703 (11)
H22A	−0.3473	0.6978	0.0634	0.105*
H22B	−0.2646	0.5998	−0.0059	0.105*
H22C	−0.1301	0.7558	0.0587	0.105*
S1	0.21539 (12)	0.42043 (10)	0.33376 (5)	0.0459 (2)
S2	−0.15010 (12)	0.18724 (10)	0.24649 (5)	0.0463 (3)
O1	0.1014 (3)	0.5258 (3)	0.35325 (13)	0.0608 (7)
O2	0.3882 (3)	0.4819 (3)	0.30225 (12)	0.0556 (6)
O3	−0.2238 (3)	0.2258 (3)	0.31952 (13)	0.0610 (7)
O4	−0.2068 (3)	0.0159 (3)	0.19840 (14)	0.0591 (7)
N1	0.0840 (3)	0.2420 (3)	0.26533 (14)	0.0391 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0376 (19)	0.0415 (19)	0.0474 (19)	0.0163 (16)	−0.0025 (16)	0.0090 (16)
C2	0.0392 (19)	0.0467 (19)	0.0449 (19)	0.0117 (16)	−0.0030 (15)	0.0144 (16)
C3	0.036 (2)	0.051 (2)	0.051 (2)	0.0206 (17)	0.0014 (16)	0.0036 (17)
C4	0.051 (2)	0.060 (2)	0.060 (2)	0.0245 (19)	0.0056 (19)	0.0086 (19)
C5	0.055 (2)	0.073 (3)	0.052 (2)	0.024 (2)	0.0149 (19)	0.023 (2)
C6	0.050 (2)	0.052 (2)	0.049 (2)	0.0225 (18)	0.0090 (17)	0.0189 (17)
C7	0.060 (2)	0.049 (2)	0.056 (2)	0.0148 (18)	0.0050 (18)	0.0190 (18)
C8	0.073 (3)	0.061 (2)	0.086 (3)	0.038 (2)	0.010 (2)	0.018 (2)
C9	0.046 (2)	0.0410 (19)	0.0442 (19)	0.0171 (16)	0.0063 (16)	0.0090 (16)
C10	0.054 (2)	0.058 (2)	0.051 (2)	0.0271 (19)	0.0175 (18)	0.0163 (18)
C11	0.062 (3)	0.064 (2)	0.047 (2)	0.020 (2)	0.0189 (19)	0.0160 (19)
C12	0.057 (2)	0.042 (2)	0.047 (2)	0.0137 (17)	0.0012 (18)	0.0095 (17)
C13	0.052 (2)	0.050 (2)	0.060 (2)	0.0246 (18)	0.0004 (19)	0.0097 (19)
C14	0.045 (2)	0.0447 (19)	0.048 (2)	0.0145 (17)	0.0085 (17)	0.0073 (16)
C15	0.089 (3)	0.064 (3)	0.062 (2)	0.020 (2)	0.000 (2)	0.024 (2)
C16	0.0370 (19)	0.0437 (19)	0.051 (2)	0.0186 (16)	0.0045 (16)	0.0171 (16)
C17	0.047 (2)	0.046 (2)	0.053 (2)	0.0212 (17)	0.0038 (17)	0.0080 (17)
C18	0.050 (2)	0.060 (2)	0.0431 (19)	0.0199 (19)	0.0062 (17)	0.0125 (18)
C19	0.044 (2)	0.053 (2)	0.053 (2)	0.0193 (18)	0.0010 (17)	0.0174 (18)
C20	0.056 (2)	0.047 (2)	0.058 (2)	0.0279 (18)	0.0057 (18)	0.0152 (18)
C21	0.042 (2)	0.052 (2)	0.049 (2)	0.0246 (17)	0.0092 (16)	0.0157 (17)
C22	0.084 (3)	0.078 (3)	0.068 (3)	0.043 (2)	0.008 (2)	0.034 (2)
S1	0.0543 (6)	0.0368 (5)	0.0494 (5)	0.0175 (4)	0.0080 (4)	0.0127 (4)
S2	0.0412 (5)	0.0448 (5)	0.0622 (6)	0.0189 (4)	0.0124 (4)	0.0242 (5)
O1	0.0785 (18)	0.0464 (14)	0.0692 (16)	0.0382 (14)	0.0113 (14)	0.0123 (12)
O2	0.0524 (15)	0.0477 (14)	0.0604 (15)	0.0034 (12)	0.0131 (12)	0.0193 (12)
O3	0.0601 (16)	0.0763 (17)	0.0700 (16)	0.0367 (14)	0.0329 (14)	0.0406 (14)
O4	0.0485 (15)	0.0355 (13)	0.0910 (18)	0.0114 (11)	0.0001 (13)	0.0159 (13)
N1	0.0349 (15)	0.0394 (15)	0.0456 (15)	0.0154 (13)	0.0042 (12)	0.0112 (13)

Geometric parameters (Å, º) top

C1—C2	1.387 (4)	C13—C14	1.386 (4)
C1—C6	1.396 (4)	C13—H13	0.9300
C1—N1	1.452 (3)	C14—H14	0.9300
C2—C3	1.409 (4)	C15—H15A	0.9600
C2—C7	1.487 (4)	C15—H15B	0.9600
C3—C4	1.374 (4)	C15—H15C	0.9600
C3—C8	1.498 (4)	C16—C21	1.375 (4)
C4—C5	1.393 (4)	C16—C17	1.383 (4)
C4—H4	0.9300	C16—S2	1.758 (3)
C5—C6	1.356 (4)	C17—C18	1.365 (4)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.383 (4)
C7—H7A	0.9600	C18—H18	0.9300
C7—H7B	0.9600	C19—C20	1.374 (4)
C7—H7C	0.9600	C19—C22	1.506 (4)
C8—H8A	0.9600	C20—C21	1.377 (4)
C8—H8B	0.9600	C20—H20	0.9300
C8—H8C	0.9600	C21—H21	0.9300
C9—C14	1.385 (4)	C22—H22A	0.9600
C9—C10	1.385 (4)	C22—H22B	0.9600
C9—S1	1.744 (3)	C22—H22C	0.9600
C10—C11	1.362 (4)	S1—O1	1.419 (2)
C10—H10	0.9300	S1—O2	1.423 (2)
C11—C12	1.379 (4)	S1—N1	1.689 (3)
C11—H11	0.9300	S2—O3	1.419 (2)
C12—C13	1.379 (4)	S2—O4	1.422 (2)
C12—C15	1.500 (4)	S2—N1	1.682 (2)

C2—C1—C6	122.1 (3)	C13—C14—H14	120.7
C2—C1—N1	120.2 (3)	C12—C15—H15A	109.5
C6—C1—N1	117.7 (2)	C12—C15—H15B	109.5
C1—C2—C3	117.6 (3)	H15A—C15—H15B	109.5
C1—C2—C7	122.0 (3)	C12—C15—H15C	109.5
C3—C2—C7	120.4 (3)	H15A—C15—H15C	109.5
C4—C3—C2	119.9 (3)	H15B—C15—H15C	109.5
C4—C3—C8	119.6 (3)	C21—C16—C17	120.3 (3)
C2—C3—C8	120.5 (3)	C21—C16—S2	120.1 (2)
C3—C4—C5	121.0 (3)	C17—C16—S2	119.5 (2)
C3—C4—H4	119.5	C18—C17—C16	119.3 (3)
C5—C4—H4	119.5	C18—C17—H17	120.4
C6—C5—C4	120.2 (3)	C16—C17—H17	120.4
C6—C5—H5	119.9	C17—C18—C19	121.5 (3)
C4—C5—H5	119.9	C17—C18—H18	119.2
C5—C6—C1	119.2 (3)	C19—C18—H18	119.2
C5—C6—H6	120.4	C20—C19—C18	118.1 (3)
C1—C6—H6	120.4	C20—C19—C22	120.7 (3)
C2—C7—H7A	109.5	C18—C19—C22	121.1 (3)
C2—C7—H7B	109.5	C19—C20—C21	121.4 (3)
H7A—C7—H7B	109.5	C19—C20—H20	119.3
C2—C7—H7C	109.5	C21—C20—H20	119.3
H7A—C7—H7C	109.5	C16—C21—C20	119.2 (3)
H7B—C7—H7C	109.5	C16—C21—H21	120.4
C3—C8—H8A	109.5	C20—C21—H21	120.4
C3—C8—H8B	109.5	C19—C22—H22A	109.5
H8A—C8—H8B	109.5	C19—C22—H22B	109.5
C3—C8—H8C	109.5	H22A—C22—H22B	109.5
H8A—C8—H8C	109.5	C19—C22—H22C	109.5
H8B—C8—H8C	109.5	H22A—C22—H22C	109.5
C14—C9—C10	120.9 (3)	H22B—C22—H22C	109.5
C14—C9—S1	119.0 (2)	O1—S1—O2	120.61 (13)
C10—C9—S1	120.1 (2)	O1—S1—N1	106.68 (13)
C11—C10—C9	118.6 (3)	O2—S1—N1	105.80 (12)
C11—C10—H10	120.7	O1—S1—C9	109.75 (14)
C9—C10—H10	120.7	O2—S1—C9	108.68 (14)
C10—C11—C12	122.5 (3)	N1—S1—C9	103.99 (13)
C10—C11—H11	118.7	O3—S2—O4	120.69 (14)
C12—C11—H11	118.7	O3—S2—N1	107.89 (14)
C11—C12—C13	118.0 (3)	O4—S2—N1	104.27 (12)
C11—C12—C15	121.5 (3)	O3—S2—C16	109.27 (13)
C13—C12—C15	120.5 (3)	O4—S2—C16	108.54 (14)
C12—C13—C14	121.4 (3)	N1—S2—C16	105.04 (12)
C12—C13—H13	119.3	C1—N1—S2	118.5 (2)
C14—C13—H13	119.3	C1—N1—S1	117.88 (19)
C9—C14—C13	118.6 (3)	S2—N1—S1	123.06 (14)
C9—C14—H14	120.7

C6—C1—C2—C3	−0.8 (5)	C17—C16—C21—C20	−1.4 (5)
N1—C1—C2—C3	178.6 (3)	S2—C16—C21—C20	179.1 (2)
C6—C1—C2—C7	178.9 (3)	C19—C20—C21—C16	−1.1 (5)
N1—C1—C2—C7	−1.7 (5)	C14—C9—S1—O1	−151.8 (3)
C1—C2—C3—C4	0.2 (5)	C10—C9—S1—O1	30.0 (3)
C7—C2—C3—C4	−179.5 (3)	C14—C9—S1—O2	−18.0 (3)
C1—C2—C3—C8	−179.2 (3)	C10—C9—S1—O2	163.8 (3)
C7—C2—C3—C8	1.1 (5)	C14—C9—S1—N1	94.4 (3)
C2—C3—C4—C5	0.6 (5)	C10—C9—S1—N1	−83.8 (3)
C8—C3—C4—C5	−179.9 (3)	C21—C16—S2—O3	12.9 (3)
C3—C4—C5—C6	−0.9 (6)	C17—C16—S2—O3	−166.5 (3)
C4—C5—C6—C1	0.3 (5)	C21—C16—S2—O4	146.4 (3)
C2—C1—C6—C5	0.6 (5)	C17—C16—S2—O4	−33.1 (3)
N1—C1—C6—C5	−178.9 (3)	C21—C16—S2—N1	−102.6 (3)
C14—C9—C10—C11	−1.2 (5)	C17—C16—S2—N1	78.0 (3)
S1—C9—C10—C11	177.0 (3)	C2—C1—N1—S2	−87.0 (3)
C9—C10—C11—C12	0.2 (5)	C6—C1—N1—S2	92.5 (3)
C10—C11—C12—C13	0.7 (5)	C2—C1—N1—S1	101.4 (3)
C10—C11—C12—C15	−178.4 (3)	C6—C1—N1—S1	−79.1 (3)
C11—C12—C13—C14	−0.6 (5)	O3—S2—N1—C1	149.88 (19)
C15—C12—C13—C14	178.5 (3)	O4—S2—N1—C1	20.4 (2)
C10—C9—C14—C13	1.2 (5)	C16—S2—N1—C1	−93.7 (2)
S1—C9—C14—C13	−176.9 (2)	O3—S2—N1—S1	−39.04 (18)
C12—C13—C14—C9	−0.4 (5)	O4—S2—N1—S1	−168.49 (14)
C21—C16—C17—C18	2.4 (5)	C16—S2—N1—S1	77.43 (18)
S2—C16—C17—C18	−178.1 (2)	O1—S1—N1—C1	156.45 (19)
C16—C17—C18—C19	−0.9 (5)	O2—S1—N1—C1	26.9 (2)
C17—C18—C19—C20	−1.5 (5)	C9—S1—N1—C1	−87.6 (2)
C17—C18—C19—C22	178.5 (3)	O1—S1—N1—S2	−14.67 (18)
C18—C19—C20—C21	2.5 (5)	O2—S1—N1—S2	−144.26 (15)
C22—C19—C20—C21	−177.5 (3)	C9—S1—N1—S2	101.31 (17)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cgⁱ	0.96	2.96	3.912 (4)	169

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₃NO₄S₂
M_r	429.53
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.5523 (8), 8.4635 (9), 17.5004 (17)
α, β, γ (°)	103.282 (7), 91.659 (7), 108.382 (7)
V (Å³)	1026.89 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.32 × 0.23 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.913, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	16232, 4569, 2359
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.645

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.129, 0.96
No. of reflections	4569
No. of parameters	266
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.30

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cgⁱ	0.96	2.96	3.912 (4)	169

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for providing a grant under the project to strengthen the Materials Chemistry Laboratory at GC University, Lahore.

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Mughal, S. Y., Khan, I. U., Harrison, W. T. A., Khan, M. H. & Tahir, M. N. (2012). Acta Cryst. E68, o2973. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 10| October 2012| Page o3013

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-(2,3-Di­methyl­phen­yl)-4-methyl-N-(4-methyl­phenyl­sulfon­yl)benzene­sulfonamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

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organic compounds

N-(2,3-Dimethylphenyl)-4-methyl-N-(4-methylphenylsulfonyl)benzenesulfonamide