N-[2-(3,4-Dimeth-oxy-phen-yl)eth-yl]-N,4-dimethyl-benzene-sulfonamide.

In the title compound, C(18)H(23)NO(4)S, the dihedral angle between the two aromatic rings is 29.14 (7)°. The S atom has a distorted tetra-hedral geometry [106.15 (9)-119.54 (10)°]. The crystal structure exhibits weak C-H⋯O and π-π inter-actions.

Related literature

For the biological activity of sulfonamide derivatives, see: Chumakov et al. (2006 ▶); Kremer et al. (2006 ▶). For related structures, see: Khan et al. (2010 ▶); Sharif et al. (2010 ▶).

Experimental

Crystal data

C18H23NO4S

M = 349.43

Monoclinic,

a = 5.7814 (4) Å

b = 13.9861 (12) Å

c = 21.9791 (18) Å

β = 92.949 (4)°

V = 1774.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 295 K

0.30 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.942, T max = 0.960

18724 measured reflections

3343 independent reflections

2614 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.110

S = 1.04

3343 reflections

221 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029746/bt5588sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029746/bt5588Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029746/bt5588Isup3.cml

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

C18H23NO4S	F(000) = 744
Mr = 349.43	Dx = 1.308 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6145 reflections
a = 5.7814 (4) Å	θ = 2.4–25.5°
b = 13.9861 (12) Å	µ = 0.20 mm−1
c = 21.9791 (18) Å	T = 295 K
β = 92.949 (4)°	Block, colourless
V = 1774.9 (2) Å3	0.30 × 0.24 × 0.20 mm
Z = 4

Bruker Kappa APEXII diffractometer	3343 independent reflections
Radiation source: fine-focus sealed tube	2614 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω and φ scans	θmax = 25.8°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→7
Tmin = 0.942, Tmax = 0.960	k = −16→17
18724 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0471P)2 + 0.6472P] where P = (Fo2 + 2Fc2)/3
3343 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.19 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.

	x	y	z	Uiso*/Ueq
S1	0.58829 (8)	0.85799 (4)	0.11159 (2)	0.04660 (17)
O1	0.6833 (3)	0.87108 (11)	0.05383 (7)	0.0609 (4)
O2	0.7388 (3)	0.84655 (12)	0.16418 (7)	0.0663 (5)
O3	0.0375 (3)	0.48564 (11)	−0.16121 (7)	0.0607 (4)
O4	−0.3215 (2)	0.58964 (12)	−0.18094 (6)	0.0612 (4)
N1	0.4284 (3)	0.76123 (11)	0.10662 (7)	0.0430 (4)
C1	0.3980 (3)	0.95272 (13)	0.12431 (8)	0.0425 (4)
C2	0.3502 (4)	0.97724 (15)	0.18308 (9)	0.0537 (5)
H2	0.4308	0.9487	0.2160	0.064*
C3	0.1823 (4)	1.04423 (16)	0.19236 (11)	0.0628 (6)
H3	0.1501	1.0610	0.2320	0.075*
C4	0.0602 (4)	1.08733 (15)	0.14425 (11)	0.0597 (6)
C5	0.1148 (4)	1.06328 (16)	0.08611 (11)	0.0615 (6)
H5	0.0368	1.0929	0.0532	0.074*
C6	0.2822 (4)	0.99631 (15)	0.07548 (9)	0.0522 (5)
H6	0.3167	0.9807	0.0358	0.063*
C7	−0.1298 (5)	1.15787 (19)	0.15501 (15)	0.0872 (9)
H7A	−0.0652	1.2209	0.1591	0.131*
H7B	−0.2038	1.1412	0.1916	0.131*
H7C	−0.2416	1.1565	0.1212	0.131*
C8	0.3156 (4)	0.73564 (17)	0.16243 (10)	0.0587 (6)
H8A	0.1778	0.7732	0.1656	0.088*
H8B	0.4194	0.7478	0.1971	0.088*
H8C	0.2755	0.6690	0.1613	0.088*
C9	0.2771 (4)	0.75162 (14)	0.05110 (9)	0.0492 (5)
H9A	0.3440	0.7863	0.0181	0.059*
H9B	0.1272	0.7796	0.0580	0.059*
C10	0.2458 (4)	0.64822 (14)	0.03316 (9)	0.0497 (5)
H10A	0.3961	0.6211	0.0256	0.060*
H10B	0.1841	0.6135	0.0669	0.060*
C11	0.0868 (3)	0.63423 (13)	−0.02258 (8)	0.0408 (4)
C12	−0.1148 (3)	0.68548 (15)	−0.03237 (9)	0.0489 (5)
H12	−0.1572	0.7298	−0.0034	0.059*
C13	−0.2558 (3)	0.67224 (15)	−0.08459 (9)	0.0498 (5)
H13	−0.3904	0.7082	−0.0905	0.060*
C14	−0.1991 (3)	0.60677 (14)	−0.12757 (8)	0.0420 (4)
C15	0.0004 (3)	0.55133 (13)	−0.11718 (8)	0.0416 (4)
C16	0.1404 (3)	0.56603 (13)	−0.06575 (9)	0.0431 (5)
H16	0.2742	0.5296	−0.0596	0.052*
C17	0.2289 (4)	0.42275 (18)	−0.15152 (13)	0.0742 (7)
H17A	0.3703	0.4588	−0.1508	0.111*
H17B	0.2287	0.3767	−0.1839	0.111*
H17C	0.2169	0.3903	−0.1133	0.111*
C18	−0.4992 (4)	0.65515 (19)	−0.19872 (11)	0.0662 (7)
H18A	−0.6191	0.6526	−0.1701	0.099*
H18B	−0.5626	0.6386	−0.2386	0.099*
H18C	−0.4363	0.7186	−0.1995	0.099*

	U11	U22	U33	U12	U13	U23
S1	0.0386 (3)	0.0522 (3)	0.0483 (3)	0.0061 (2)	−0.0042 (2)	−0.0112 (2)
O1	0.0549 (9)	0.0663 (10)	0.0630 (10)	0.0020 (7)	0.0177 (7)	−0.0123 (8)
O2	0.0512 (8)	0.0763 (11)	0.0685 (10)	0.0111 (8)	−0.0249 (7)	−0.0178 (8)
O3	0.0600 (9)	0.0594 (9)	0.0614 (9)	0.0207 (7)	−0.0094 (7)	−0.0241 (7)
O4	0.0541 (8)	0.0736 (11)	0.0538 (9)	0.0195 (7)	−0.0170 (7)	−0.0185 (8)
N1	0.0453 (9)	0.0435 (9)	0.0394 (9)	0.0073 (7)	−0.0075 (7)	−0.0039 (7)
C1	0.0457 (10)	0.0391 (10)	0.0425 (11)	0.0008 (8)	0.0010 (8)	−0.0059 (8)
C2	0.0714 (14)	0.0478 (12)	0.0420 (12)	0.0067 (10)	0.0031 (10)	−0.0046 (9)
C3	0.0869 (17)	0.0490 (13)	0.0548 (14)	0.0079 (12)	0.0246 (12)	−0.0054 (11)
C4	0.0648 (14)	0.0407 (12)	0.0757 (16)	0.0065 (10)	0.0224 (12)	0.0010 (11)
C5	0.0687 (14)	0.0523 (13)	0.0631 (14)	0.0140 (11)	−0.0003 (11)	0.0081 (11)
C6	0.0634 (13)	0.0507 (12)	0.0426 (11)	0.0062 (10)	0.0041 (9)	−0.0023 (9)
C7	0.0838 (18)	0.0608 (16)	0.120 (2)	0.0226 (14)	0.0352 (17)	0.0052 (16)
C8	0.0647 (14)	0.0592 (14)	0.0520 (13)	0.0055 (11)	0.0017 (10)	−0.0009 (11)
C9	0.0508 (11)	0.0448 (11)	0.0501 (12)	0.0040 (9)	−0.0139 (9)	−0.0035 (9)
C10	0.0555 (12)	0.0445 (12)	0.0480 (12)	0.0055 (9)	−0.0088 (9)	−0.0028 (9)
C11	0.0425 (10)	0.0379 (10)	0.0416 (11)	0.0011 (8)	−0.0021 (8)	−0.0006 (8)
C12	0.0471 (11)	0.0535 (12)	0.0459 (11)	0.0088 (9)	0.0014 (9)	−0.0142 (9)
C13	0.0390 (10)	0.0563 (12)	0.0536 (12)	0.0140 (9)	−0.0031 (9)	−0.0107 (10)
C14	0.0378 (9)	0.0457 (11)	0.0420 (11)	0.0025 (8)	−0.0031 (8)	−0.0035 (9)
C15	0.0424 (10)	0.0368 (10)	0.0453 (11)	0.0031 (8)	0.0012 (8)	−0.0068 (8)
C16	0.0407 (10)	0.0354 (10)	0.0525 (12)	0.0076 (8)	−0.0036 (8)	−0.0023 (9)
C17	0.0615 (14)	0.0631 (16)	0.0972 (19)	0.0222 (12)	−0.0040 (13)	−0.0318 (14)
C18	0.0567 (13)	0.0845 (18)	0.0556 (14)	0.0189 (12)	−0.0147 (11)	−0.0004 (12)

S1—O2	1.4195 (15)	C8—H8A	0.9600
S1—O1	1.4210 (15)	C8—H8B	0.9600
S1—N1	1.6391 (17)	C8—H8C	0.9600
S1—C1	1.7538 (19)	C9—C10	1.507 (3)
O3—C15	1.359 (2)	C9—H9A	0.9700
O3—C17	1.421 (3)	C9—H9B	0.9700
O4—C14	1.360 (2)	C10—C11	1.506 (3)
O4—C18	1.417 (2)	C10—H10A	0.9700
N1—C8	1.463 (3)	C10—H10B	0.9700
N1—C9	1.471 (2)	C11—C12	1.376 (3)
C1—C6	1.378 (3)	C11—C16	1.392 (3)
C1—C2	1.378 (3)	C12—C13	1.386 (3)
C2—C3	1.372 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.367 (3)
C3—C4	1.380 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.399 (3)
C4—C5	1.374 (3)	C15—C16	1.372 (2)
C4—C7	1.504 (3)	C16—H16	0.9300
C5—C6	1.375 (3)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C7—H7A	0.9600	C18—H18A	0.9600
C7—H7B	0.9600	C18—H18B	0.9600
C7—H7C	0.9600	C18—H18C	0.9600
O2—S1—O1	119.54 (10)	N1—C9—H9A	109.4
O2—S1—N1	106.32 (9)	C10—C9—H9A	109.4
O1—S1—N1	106.83 (9)	N1—C9—H9B	109.4
O2—S1—C1	108.57 (9)	C10—C9—H9B	109.4
O1—S1—C1	108.64 (9)	H9A—C9—H9B	108.0
N1—S1—C1	106.15 (9)	C11—C10—C9	113.42 (16)
C15—O3—C17	117.52 (16)	C11—C10—H10A	108.9
C14—O4—C18	117.51 (16)	C9—C10—H10A	108.9
C8—N1—C9	113.66 (16)	C11—C10—H10B	108.9
C8—N1—S1	114.86 (13)	C9—C10—H10B	108.9
C9—N1—S1	116.11 (13)	H10A—C10—H10B	107.7
C6—C1—C2	120.49 (18)	C12—C11—C16	117.84 (17)
C6—C1—S1	119.59 (15)	C12—C11—C10	122.44 (17)
C2—C1—S1	119.67 (15)	C16—C11—C10	119.71 (16)
C3—C2—C1	119.1 (2)	C11—C12—C13	121.17 (18)
C3—C2—H2	120.4	C11—C12—H12	119.4
C1—C2—H2	120.4	C13—C12—H12	119.4
C2—C3—C4	121.5 (2)	C14—C13—C12	120.65 (18)
C2—C3—H3	119.2	C14—C13—H13	119.7
C4—C3—H3	119.2	C12—C13—H13	119.7
C5—C4—C3	118.2 (2)	O4—C14—C13	125.54 (17)
C5—C4—C7	120.8 (2)	O4—C14—C15	115.54 (16)
C3—C4—C7	121.0 (2)	C13—C14—C15	118.91 (17)
C4—C5—C6	121.5 (2)	O3—C15—C16	125.43 (17)
C4—C5—H5	119.3	O3—C15—C14	114.69 (16)
C6—C5—H5	119.3	C16—C15—C14	119.88 (17)
C5—C6—C1	119.15 (19)	C15—C16—C11	121.46 (17)
C5—C6—H6	120.4	C15—C16—H16	119.3
C1—C6—H6	120.4	C11—C16—H16	119.3
C4—C7—H7A	109.5	O3—C17—H17A	109.5
C4—C7—H7B	109.5	O3—C17—H17B	109.5
H7A—C7—H7B	109.5	H17A—C17—H17B	109.5
C4—C7—H7C	109.5	O3—C17—H17C	109.5
H7A—C7—H7C	109.5	H17A—C17—H17C	109.5
H7B—C7—H7C	109.5	H17B—C17—H17C	109.5
N1—C8—H8A	109.5	O4—C18—H18A	109.5
N1—C8—H8B	109.5	O4—C18—H18B	109.5
H8A—C8—H8B	109.5	H18A—C18—H18B	109.5
N1—C8—H8C	109.5	O4—C18—H18C	109.5
H8A—C8—H8C	109.5	H18A—C18—H18C	109.5
H8B—C8—H8C	109.5	H18B—C18—H18C	109.5
N1—C9—C10	111.29 (16)
O2—S1—N1—C8	51.06 (16)	C8—N1—C9—C10	−75.5 (2)
O1—S1—N1—C8	179.76 (14)	S1—N1—C9—C10	147.97 (15)
C1—S1—N1—C8	−64.43 (15)	N1—C9—C10—C11	178.43 (16)
O2—S1—N1—C9	−172.91 (13)	C9—C10—C11—C12	−41.2 (3)
O1—S1—N1—C9	−44.21 (15)	C9—C10—C11—C16	140.1 (2)
C1—S1—N1—C9	71.59 (15)	C16—C11—C12—C13	−2.3 (3)
O2—S1—C1—C6	161.10 (17)	C10—C11—C12—C13	178.9 (2)
O1—S1—C1—C6	29.63 (19)	C11—C12—C13—C14	0.8 (3)
N1—S1—C1—C6	−84.94 (18)	C18—O4—C14—C13	11.4 (3)
O2—S1—C1—C2	−24.6 (2)	C18—O4—C14—C15	−168.70 (19)
O1—S1—C1—C2	−156.06 (17)	C12—C13—C14—O4	−178.3 (2)
N1—S1—C1—C2	89.36 (18)	C12—C13—C14—C15	1.8 (3)
C6—C1—C2—C3	1.4 (3)	C17—O3—C15—C16	4.2 (3)
S1—C1—C2—C3	−172.90 (17)	C17—O3—C15—C14	−176.0 (2)
C1—C2—C3—C4	0.1 (4)	O4—C14—C15—O3	−2.4 (3)
C2—C3—C4—C5	−1.6 (4)	C13—C14—C15—O3	177.47 (19)
C2—C3—C4—C7	177.6 (2)	O4—C14—C15—C16	177.38 (18)
C3—C4—C5—C6	1.7 (4)	C13—C14—C15—C16	−2.7 (3)
C7—C4—C5—C6	−177.6 (2)	O3—C15—C16—C11	−179.08 (18)
C4—C5—C6—C1	−0.2 (3)	C14—C15—C16—C11	1.2 (3)
C2—C1—C6—C5	−1.3 (3)	C12—C11—C16—C15	1.4 (3)
S1—C1—C6—C5	172.95 (17)	C10—C11—C16—C15	−179.82 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.59	2.942 (3)	103
C8—H8B···O2	0.96	2.44	2.895 (3)	109
C9—H9A···O1	0.97	2.39	2.880 (3)	111
C12—H12···O1i	0.93	2.54	3.452 (2)	166
C18—H18B···O2ii	0.96	2.38	3.302 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1i	0.93	2.54	3.452 (2)	166
C18—H18B⋯O2ii	0.96	2.38	3.302 (3)	160

Symmetry codes: (i) ; (ii) .