N-(2,3-Dimethyl-phen-yl)-4-methyl-N-(4-methyl-phenyl-sulfon-yl)benzene-sulfonamide.

In the title compound, C(22)H(23)NO(4)S(2), the dihedral angles between the dimethyl-phenyl ring and the two methyl-phenyl rings are 41.19 (15) and 20.50 (17)°; the dihedral angle between the methyl-phenyl rings is 48.11 (14)°. The C-N-S-C torsion angles are -87.6 (2) and 77.43 (18)°. The only possible directional inter-actions in the crystal are very weak C-H⋯π inter-actions and very weak π-π stacking between parallel methyl-phenyl 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 = 429.53

Triclinic,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.129

S = 0.96

4569 reflections

266 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.30 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039773/xu5622sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039773/xu5622Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039773/xu5622Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H23NO4S2	Z = 2
Mr = 429.53	F(000) = 452
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.052P)2] where P = (Fo2 + 2Fc2)/3
4569 reflections	(Δ/σ)max = 0.002
266 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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⋯Cg i	0.96	2.96	3.912 (4)	169

Symmetry code: (i) .