N-{4-[(3,4-Dimethyl-phen-yl)(eth-yl)sulfamo-yl]phen-yl}-N-ethyl-acetamide.

When viewed down the central S⋯N axis of the title compound, C(20)H(26)N(2)O(3)S, it is apparent that the mol-ecule adopts a gauche conformation with all O atoms lying to one side of the central benzene ring; the carbonyl O atom is directed away from the central ring and the N-bound ethyl groups lie to one side of the mol-ecule. Supra-molecular helical chains aligned along the b axis and sustained by C-H⋯O contacts feature in the crystal packing. These are consolidated in the three-dimensional structure by C-H⋯π inter-actions.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For related structures, see: Sharif et al. (2010 ▶); Khan et al. (2010 ▶).

Experimental

Crystal data

C20H26N2O3S

M = 374.51

Monoclinic,

a = 8.0882 (2) Å

b = 11.5978 (3) Å

c = 21.2717 (5) Å

β = 97.194 (1)°

V = 1979.69 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 293 K

0.28 × 0.14 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.692, T max = 0.895

16612 measured reflections

4079 independent reflections

3325 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.122

S = 1.01

4079 reflections

240 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAIn class="Chemical">NT (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 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045708/hg2743sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045708/hg2743Isup2.hkl

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

C20H26N2O3S	F(000) = 800
Mr = 374.51	Dx = 1.257 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7015 reflections
a = 8.0882 (2) Å	θ = 3.0–27.8°
b = 11.5978 (3) Å	µ = 0.19 mm−1
c = 21.2717 (5) Å	T = 293 K
β = 97.194 (1)°	Block, colourless
V = 1979.69 (8) Å3	0.28 × 0.14 × 0.08 mm
Z = 4

Bruker APEXII CCD diffractometer	4079 independent reflections
Radiation source: fine-focus sealed tube	3325 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 26.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.692, Tmax = 0.895	k = −14→11
16612 measured reflections	l = −26→26

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) = 0.122	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0713P)2 + 0.4585P] where P = (Fo2 + 2Fc2)/3
4079 reflections	(Δ/σ)max = 0.001
240 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1	1.12740 (5)	0.72075 (4)	0.249229 (18)	0.03937 (14)
O1	1.07590 (16)	0.82013 (10)	0.28110 (6)	0.0509 (3)
O2	1.25922 (15)	0.73062 (12)	0.21059 (6)	0.0536 (3)
O3	0.27644 (17)	0.53664 (14)	0.04014 (7)	0.0694 (4)
N1	1.18549 (16)	0.62329 (11)	0.30379 (6)	0.0376 (3)
N2	0.52634 (17)	0.52003 (13)	0.09842 (7)	0.0475 (4)
C1	1.2726 (2)	0.52088 (16)	0.28259 (8)	0.0476 (4)
H1A	1.1913	0.4620	0.2683	0.057*
H1B	1.3306	0.5419	0.2470	0.057*
C2	1.3933 (3)	0.4738 (2)	0.33407 (12)	0.0874 (8)
H2A	1.4686	0.5337	0.3505	0.131*
H2B	1.4551	0.4123	0.3178	0.131*
H2C	1.3347	0.4450	0.3673	0.131*
C3	1.06969 (18)	0.60395 (13)	0.34975 (7)	0.0339 (3)
C4	1.06258 (19)	0.68223 (14)	0.39837 (7)	0.0389 (3)
H4	1.1336	0.7456	0.4015	0.047*
C5	0.9517 (2)	0.66828 (15)	0.44270 (7)	0.0422 (4)
C6	0.8482 (2)	0.57149 (16)	0.43848 (8)	0.0442 (4)
C7	0.8584 (2)	0.49348 (15)	0.39000 (8)	0.0488 (4)
H7	0.7902	0.4286	0.3873	0.059*
C8	0.9669 (2)	0.50905 (14)	0.34545 (8)	0.0440 (4)
H8	0.9704	0.4559	0.3129	0.053*
C9	0.9443 (3)	0.7571 (2)	0.49396 (9)	0.0631 (5)
H9A	1.0265	0.8155	0.4903	0.095*
H9B	0.9660	0.7207	0.5347	0.095*
H9C	0.8355	0.7916	0.4896	0.095*
C10	0.7272 (3)	0.5500 (2)	0.48570 (10)	0.0673 (6)
H10A	0.7868	0.5468	0.5276	0.101*
H10B	0.6708	0.4781	0.4761	0.101*
H10C	0.6471	0.6114	0.4834	0.101*
C11	0.95077 (19)	0.66426 (14)	0.20256 (7)	0.0377 (3)
C12	0.7959 (2)	0.68032 (16)	0.22264 (8)	0.0454 (4)
H12	0.7859	0.7231	0.2589	0.055*
C13	0.6567 (2)	0.63238 (16)	0.18843 (8)	0.0477 (4)
H13	0.5526	0.6421	0.2020	0.057*
C14	0.67146 (19)	0.56991 (14)	0.13400 (8)	0.0410 (4)
C15	0.8263 (2)	0.55379 (15)	0.11401 (8)	0.0435 (4)
H15	0.8359	0.5115	0.0775	0.052*
C16	0.96666 (19)	0.60077 (15)	0.14841 (7)	0.0422 (4)
H16	1.0710	0.5898	0.1353	0.051*
C17	0.5128 (2)	0.39364 (17)	0.09782 (10)	0.0592 (5)
H17A	0.6237	0.3608	0.1001	0.071*
H17B	0.4510	0.3697	0.0579	0.071*
C18	0.4287 (4)	0.3465 (2)	0.15098 (12)	0.0839 (7)
H18A	0.4904	0.3684	0.1907	0.126*
H18B	0.4241	0.2639	0.1480	0.126*
H18C	0.3177	0.3768	0.1484	0.126*
C19	0.4017 (2)	0.58325 (17)	0.06710 (8)	0.0485 (4)
C20	0.4223 (3)	0.71197 (17)	0.06548 (9)	0.0564 (5)
H20A	0.3588	0.7423	0.0280	0.085*
H20B	0.5379	0.7305	0.0652	0.085*
H20C	0.3834	0.7454	0.1022	0.085*

	U11	U22	U33	U12	U13	U23
S1	0.0372 (2)	0.0426 (3)	0.0387 (2)	−0.00274 (16)	0.00612 (16)	0.00737 (16)
O1	0.0619 (8)	0.0375 (6)	0.0527 (7)	0.0004 (6)	0.0049 (6)	0.0032 (5)
O2	0.0408 (6)	0.0717 (9)	0.0498 (7)	−0.0092 (6)	0.0114 (5)	0.0127 (6)
O3	0.0518 (8)	0.0747 (10)	0.0762 (9)	−0.0066 (7)	−0.0140 (7)	−0.0079 (8)
N1	0.0376 (7)	0.0394 (7)	0.0365 (6)	0.0037 (5)	0.0071 (5)	0.0036 (5)
N2	0.0397 (7)	0.0436 (8)	0.0584 (9)	0.0001 (6)	0.0028 (6)	−0.0044 (7)
C1	0.0457 (9)	0.0479 (10)	0.0514 (9)	0.0085 (8)	0.0142 (8)	0.0004 (8)
C2	0.0891 (17)	0.0869 (18)	0.0821 (16)	0.0473 (14)	−0.0048 (13)	0.0050 (14)
C3	0.0342 (7)	0.0354 (8)	0.0323 (7)	−0.0006 (6)	0.0043 (6)	0.0021 (6)
C4	0.0388 (8)	0.0380 (8)	0.0392 (8)	−0.0052 (7)	0.0018 (6)	−0.0018 (6)
C5	0.0413 (8)	0.0477 (9)	0.0367 (8)	0.0048 (7)	0.0021 (7)	−0.0035 (7)
C6	0.0393 (8)	0.0528 (10)	0.0416 (8)	0.0021 (7)	0.0086 (7)	0.0060 (7)
C7	0.0494 (10)	0.0434 (9)	0.0544 (10)	−0.0142 (8)	0.0095 (8)	0.0013 (8)
C8	0.0530 (10)	0.0379 (9)	0.0416 (8)	−0.0073 (7)	0.0082 (7)	−0.0068 (7)
C9	0.0642 (12)	0.0715 (13)	0.0544 (11)	0.0027 (10)	0.0107 (10)	−0.0209 (10)
C10	0.0596 (12)	0.0847 (16)	0.0622 (11)	−0.0031 (11)	0.0254 (10)	0.0073 (11)
C11	0.0340 (8)	0.0451 (9)	0.0343 (7)	0.0036 (7)	0.0061 (6)	0.0065 (7)
C12	0.0404 (9)	0.0559 (10)	0.0414 (8)	0.0047 (8)	0.0104 (7)	−0.0042 (8)
C13	0.0339 (8)	0.0619 (11)	0.0490 (9)	0.0029 (8)	0.0122 (7)	−0.0034 (8)
C14	0.0351 (8)	0.0438 (9)	0.0439 (8)	0.0014 (7)	0.0038 (7)	0.0027 (7)
C15	0.0428 (9)	0.0504 (10)	0.0380 (8)	0.0055 (7)	0.0080 (7)	−0.0016 (7)
C16	0.0344 (8)	0.0541 (10)	0.0396 (8)	0.0058 (7)	0.0110 (6)	0.0046 (7)
C17	0.0519 (11)	0.0488 (11)	0.0774 (13)	0.0015 (8)	0.0105 (9)	−0.0121 (10)
C18	0.112 (2)	0.0563 (13)	0.0870 (16)	−0.0039 (13)	0.0250 (15)	0.0065 (12)
C19	0.0429 (9)	0.0578 (11)	0.0445 (9)	0.0004 (8)	0.0043 (7)	−0.0042 (8)
C20	0.0589 (11)	0.0538 (11)	0.0549 (10)	0.0054 (9)	0.0002 (9)	0.0030 (9)

S1—O1	1.4256 (13)	C9—H9A	0.9600
S1—O2	1.4301 (12)	C9—H9B	0.9600
S1—N1	1.6458 (13)	C9—H9C	0.9600
S1—C11	1.7608 (16)	C10—H10A	0.9600
O3—C19	1.226 (2)	C10—H10B	0.9600
N1—C3	1.4534 (18)	C10—H10C	0.9600
N1—C1	1.480 (2)	C11—C12	1.386 (2)
N2—C19	1.352 (2)	C11—C16	1.386 (2)
N2—C14	1.436 (2)	C12—C13	1.379 (2)
N2—C17	1.470 (2)	C12—H12	0.9300
C1—C2	1.478 (3)	C13—C14	1.384 (2)
C1—H1A	0.9700	C13—H13	0.9300
C1—H1B	0.9700	C14—C15	1.385 (2)
C2—H2A	0.9600	C15—C16	1.383 (2)
C2—H2B	0.9600	C15—H15	0.9300
C2—H2C	0.9600	C16—H16	0.9300
C3—C8	1.376 (2)	C17—C18	1.494 (3)
C3—C4	1.383 (2)	C17—H17A	0.9700
C4—C5	1.390 (2)	C17—H17B	0.9700
C4—H4	0.9300	C18—H18A	0.9600
C5—C6	1.396 (2)	C18—H18B	0.9600
C5—C9	1.506 (2)	C18—H18C	0.9600
C6—C7	1.382 (2)	C19—C20	1.503 (3)
C6—C10	1.508 (2)	C20—H20A	0.9600
C7—C8	1.382 (2)	C20—H20B	0.9600
C7—H7	0.9300	C20—H20C	0.9600
C8—H8	0.9300
O1—S1—O2	119.46 (8)	H9B—C9—H9C	109.5
O1—S1—N1	107.13 (7)	C6—C10—H10A	109.5
O2—S1—N1	107.03 (7)	C6—C10—H10B	109.5
O1—S1—C11	107.71 (8)	H10A—C10—H10B	109.5
O2—S1—C11	108.45 (7)	C6—C10—H10C	109.5
N1—S1—C11	106.37 (7)	H10A—C10—H10C	109.5
C3—N1—C1	116.91 (12)	H10B—C10—H10C	109.5
C3—N1—S1	115.41 (10)	C12—C11—C16	120.59 (15)
C1—N1—S1	116.17 (10)	C12—C11—S1	118.50 (12)
C19—N2—C14	123.41 (15)	C16—C11—S1	120.86 (12)
C19—N2—C17	119.09 (15)	C13—C12—C11	119.53 (15)
C14—N2—C17	117.48 (15)	C13—C12—H12	120.2
C2—C1—N1	111.47 (16)	C11—C12—H12	120.2
C2—C1—H1A	109.3	C12—C13—C14	120.17 (15)
N1—C1—H1A	109.3	C12—C13—H13	119.9
C2—C1—H1B	109.3	C14—C13—H13	119.9
N1—C1—H1B	109.3	C15—C14—C13	120.26 (15)
H1A—C1—H1B	108.0	C15—C14—N2	119.64 (15)
C1—C2—H2A	109.5	C13—C14—N2	120.09 (14)
C1—C2—H2B	109.5	C16—C15—C14	119.88 (15)
H2A—C2—H2B	109.5	C16—C15—H15	120.1
C1—C2—H2C	109.5	C14—C15—H15	120.1
H2A—C2—H2C	109.5	C15—C16—C11	119.56 (14)
H2B—C2—H2C	109.5	C15—C16—H16	120.2
C8—C3—C4	119.57 (14)	C11—C16—H16	120.2
C8—C3—N1	120.92 (13)	N2—C17—C18	113.53 (17)
C4—C3—N1	119.50 (13)	N2—C17—H17A	108.9
C3—C4—C5	121.45 (14)	C18—C17—H17A	108.9
C3—C4—H4	119.3	N2—C17—H17B	108.9
C5—C4—H4	119.3	C18—C17—H17B	108.9
C4—C5—C6	118.84 (15)	H17A—C17—H17B	107.7
C4—C5—C9	119.93 (16)	C17—C18—H18A	109.5
C6—C5—C9	121.23 (16)	C17—C18—H18B	109.5
C7—C6—C5	118.90 (15)	H18A—C18—H18B	109.5
C7—C6—C10	119.53 (17)	C17—C18—H18C	109.5
C5—C6—C10	121.57 (16)	H18A—C18—H18C	109.5
C8—C7—C6	121.90 (15)	H18B—C18—H18C	109.5
C8—C7—H7	119.0	O3—C19—N2	120.85 (18)
C6—C7—H7	119.0	O3—C19—C20	120.99 (18)
C3—C8—C7	119.31 (15)	N2—C19—C20	118.16 (16)
C3—C8—H8	120.3	C19—C20—H20A	109.5
C7—C8—H8	120.3	C19—C20—H20B	109.5
C5—C9—H9A	109.5	H20A—C20—H20B	109.5
C5—C9—H9B	109.5	C19—C20—H20C	109.5
H9A—C9—H9B	109.5	H20A—C20—H20C	109.5
C5—C9—H9C	109.5	H20B—C20—H20C	109.5
H9A—C9—H9C	109.5
O1—S1—N1—C3	48.43 (12)	O2—S1—C11—C12	−159.96 (14)
O2—S1—N1—C3	177.67 (10)	N1—S1—C11—C12	85.22 (14)
C11—S1—N1—C3	−66.55 (12)	O1—S1—C11—C16	153.43 (13)
O1—S1—N1—C1	−169.22 (12)	O2—S1—C11—C16	22.83 (16)
O2—S1—N1—C1	−39.98 (14)	N1—S1—C11—C16	−91.99 (14)
C11—S1—N1—C1	75.80 (13)	C16—C11—C12—C13	0.2 (3)
C3—N1—C1—C2	−68.9 (2)	S1—C11—C12—C13	−177.06 (13)
S1—N1—C1—C2	149.37 (17)	C11—C12—C13—C14	−0.8 (3)
C1—N1—C3—C8	−39.7 (2)	C12—C13—C14—C15	0.9 (3)
S1—N1—C3—C8	102.32 (16)	C12—C13—C14—N2	180.00 (16)
C1—N1—C3—C4	140.40 (15)	C19—N2—C14—C15	−114.12 (19)
S1—N1—C3—C4	−77.54 (16)	C17—N2—C14—C15	67.4 (2)
C8—C3—C4—C5	−1.0 (2)	C19—N2—C14—C13	66.8 (2)
N1—C3—C4—C5	178.83 (13)	C17—N2—C14—C13	−111.71 (19)
C3—C4—C5—C6	1.4 (2)	C13—C14—C15—C16	−0.3 (3)
C3—C4—C5—C9	−178.33 (16)	N2—C14—C15—C16	−179.42 (15)
C4—C5—C6—C7	−0.7 (2)	C14—C15—C16—C11	−0.4 (3)
C9—C5—C6—C7	179.10 (17)	C12—C11—C16—C15	0.4 (2)
C4—C5—C6—C10	178.90 (16)	S1—C11—C16—C15	177.57 (13)
C9—C5—C6—C10	−1.3 (3)	C19—N2—C17—C18	−89.7 (2)
C5—C6—C7—C8	−0.5 (3)	C14—N2—C17—C18	88.9 (2)
C10—C6—C7—C8	179.92 (17)	C14—N2—C19—O3	−176.18 (16)
C4—C3—C8—C7	−0.2 (2)	C17—N2—C19—O3	2.3 (3)
N1—C3—C8—C7	179.99 (15)	C14—N2—C19—C20	4.7 (2)
C6—C7—C8—C3	0.9 (3)	C17—N2—C19—C20	−176.83 (17)
O1—S1—C11—C12	−29.36 (15)

Cg1 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.93	2.54	3.455 (2)	170
C10—H10a···Cg1ii	0.96	2.93	3.728 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.93	2.54	3.455 (2)	170
C10—H10a⋯Cg1ii	0.96	2.93	3.728 (2)	142

Symmetry codes: (i) ; (ii) .