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

In the title compound, C(17)H(21)NO(4)S, the phenyl and dimeth-oxy-phenyl rings are almost perpendicular to each other, making a dihedral angle of 82.57 (5)°. The structure is stabilized by inter-molecular C-H⋯O inter-actions and the packing is further enhanced by C-H ⋯π inter-actions.

Related literature

For the biological activity of sulfonamide derivatives, see: Zareef et al. (2007 ▶); Pomarnacka & Kozlarska-Kedra (2003 ▶); Siddiqui et al. (2007 ▶); Gennarte et al. (1994 ▶). For standard bond distances, see: Allen et al. (1987 ▶). For geometric parameters, see: Khan et al. (2010 ▶). For asymmetry parameters, see: Nardelli (1983 ▶).

Experimental

Crystal data

C17H21NO4S

M = 335.41

Monoclinic,

a = 9.9383 (3) Å

b = 14.6494 (4) Å

c = 12.0097 (3) Å

β = 108.535 (1)°

V = 1657.80 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.40 × 0.40 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.879, T max = 0.938

20493 measured reflections

4353 independent reflections

3342 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.115

S = 1.00

4353 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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 Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005272/sj5187sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005272/sj5187Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005272/sj5187Isup3.cml

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

C17H21NO4S	F(000) = 712
Mr = 335.41	Dx = 1.344 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7936 reflections
a = 9.9383 (3) Å	θ = 2.2–29.0°
b = 14.6494 (4) Å	µ = 0.22 mm−1
c = 12.0097 (3) Å	T = 293 K
β = 108.535 (1)°	Block, colourless
V = 1657.80 (8) Å3	0.40 × 0.40 × 0.30 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4353 independent reflections
Radiation source: fine-focus sealed tube	3342 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 29.2°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→8
Tmin = 0.879, Tmax = 0.938	k = −19→19
20493 measured reflections	l = −16→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0586P)2 + 0.383P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
4353 reflections	Δρmax = 0.27 e Å−3
212 parameters	Δρmin = −0.30 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (10)

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	0.11829 (14)	0.66352 (10)	0.73921 (12)	0.0389 (3)
C2	−0.02018 (16)	0.69298 (11)	0.71549 (15)	0.0503 (4)
H2	−0.0811	0.6630	0.7481	0.060*
C3	−0.06711 (18)	0.76743 (13)	0.64283 (16)	0.0590 (4)
H3	−0.1597	0.7881	0.6275	0.071*
C4	0.02163 (19)	0.81095 (11)	0.59322 (15)	0.0557 (4)
H4	−0.0108	0.8607	0.5440	0.067*
C5	0.15918 (18)	0.78080 (11)	0.61644 (16)	0.0548 (4)
H5	0.2191	0.8102	0.5822	0.066*
C6	0.20867 (15)	0.70752 (10)	0.68983 (15)	0.0477 (4)
H6	0.3019	0.6878	0.7060	0.057*
C7	0.01095 (18)	0.45745 (13)	0.66936 (16)	0.0588 (4)
H7A	−0.0252	0.4999	0.6060	0.088*
H7B	−0.0454	0.4605	0.7210	0.088*
H7C	0.0068	0.3968	0.6383	0.088*
C8	0.25582 (17)	0.47960 (10)	0.66388 (14)	0.0463 (3)
H8A	0.3467	0.5047	0.7102	0.056*
H8B	0.2175	0.5182	0.5955	0.056*
C9	0.2778 (2)	0.38392 (11)	0.62405 (14)	0.0531 (4)
H9A	0.1862	0.3602	0.5770	0.064*
H9B	0.3364	0.3884	0.5733	0.064*
C10	0.34519 (14)	0.31529 (10)	0.71947 (12)	0.0404 (3)
C11	0.33172 (14)	0.22281 (10)	0.68971 (12)	0.0413 (3)
H11	0.2803	0.2059	0.6134	0.050*
C12	0.39284 (14)	0.15593 (10)	0.77076 (12)	0.0399 (3)
C13	0.47154 (13)	0.18065 (10)	0.88626 (12)	0.0391 (3)
C14	0.48459 (14)	0.27165 (10)	0.91596 (12)	0.0429 (3)
H14	0.5360	0.2887	0.9922	0.051*
C15	0.42196 (14)	0.33848 (10)	0.83345 (13)	0.0437 (3)
H15	0.4319	0.3996	0.8554	0.052*
C16	0.6248 (2)	0.13091 (15)	1.07208 (15)	0.0661 (5)
H16A	0.7043	0.1641	1.0636	0.099*
H16B	0.6576	0.0755	1.1147	0.099*
H16C	0.5771	0.1676	1.1142	0.099*
C17	0.3105 (2)	0.03597 (13)	0.63220 (16)	0.0655 (5)
H17A	0.2136	0.0561	0.6104	0.098*
H17B	0.3130	−0.0294	0.6279	0.098*
H17C	0.3553	0.0619	0.5796	0.098*
N	0.15832 (12)	0.48049 (8)	0.73455 (10)	0.0398 (3)
O1	0.08318 (15)	0.54928 (9)	0.89196 (10)	0.0632 (3)
O2	0.32561 (12)	0.57504 (8)	0.88559 (10)	0.0597 (3)
O3	0.38351 (13)	0.06447 (7)	0.74855 (10)	0.0576 (3)
O4	0.52907 (12)	0.10956 (8)	0.95905 (9)	0.0554 (3)
S	0.17728 (4)	0.56558 (3)	0.82594 (3)	0.04282 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0437 (7)	0.0361 (7)	0.0379 (7)	0.0028 (5)	0.0145 (5)	−0.0021 (5)
C2	0.0480 (8)	0.0537 (9)	0.0563 (9)	0.0072 (7)	0.0267 (7)	0.0050 (7)
C3	0.0517 (9)	0.0619 (10)	0.0654 (10)	0.0210 (8)	0.0212 (8)	0.0074 (9)
C4	0.0664 (10)	0.0433 (9)	0.0581 (9)	0.0135 (7)	0.0207 (8)	0.0087 (7)
C5	0.0618 (10)	0.0416 (8)	0.0678 (11)	−0.0012 (7)	0.0302 (8)	0.0063 (8)
C6	0.0408 (7)	0.0415 (8)	0.0624 (9)	0.0015 (6)	0.0188 (6)	0.0014 (7)
C7	0.0508 (8)	0.0637 (11)	0.0547 (9)	−0.0121 (8)	0.0066 (7)	−0.0042 (8)
C8	0.0567 (8)	0.0405 (8)	0.0447 (8)	0.0030 (6)	0.0202 (7)	0.0036 (6)
C9	0.0715 (10)	0.0485 (9)	0.0413 (8)	0.0107 (8)	0.0209 (7)	−0.0004 (7)
C10	0.0421 (7)	0.0416 (8)	0.0407 (7)	0.0026 (6)	0.0175 (5)	−0.0027 (6)
C11	0.0421 (7)	0.0450 (8)	0.0355 (7)	0.0008 (6)	0.0107 (5)	−0.0069 (6)
C12	0.0386 (6)	0.0399 (7)	0.0404 (7)	0.0005 (5)	0.0115 (5)	−0.0052 (6)
C13	0.0341 (6)	0.0463 (8)	0.0366 (7)	0.0022 (5)	0.0108 (5)	−0.0026 (6)
C14	0.0356 (6)	0.0515 (8)	0.0391 (7)	−0.0031 (6)	0.0083 (5)	−0.0107 (6)
C15	0.0434 (7)	0.0401 (8)	0.0481 (8)	−0.0037 (6)	0.0153 (6)	−0.0093 (6)
C16	0.0598 (10)	0.0829 (13)	0.0438 (8)	0.0087 (9)	0.0000 (7)	0.0054 (9)
C17	0.0789 (12)	0.0467 (9)	0.0563 (10)	0.0028 (8)	0.0009 (9)	−0.0181 (8)
N	0.0436 (6)	0.0363 (6)	0.0381 (6)	−0.0006 (5)	0.0110 (5)	−0.0007 (5)
O1	0.0888 (9)	0.0641 (8)	0.0482 (6)	0.0084 (6)	0.0383 (6)	0.0079 (6)
O2	0.0581 (7)	0.0543 (7)	0.0491 (6)	0.0022 (5)	−0.0080 (5)	−0.0059 (5)
O3	0.0729 (8)	0.0390 (6)	0.0486 (6)	0.0019 (5)	0.0021 (5)	−0.0087 (5)
O4	0.0631 (7)	0.0524 (7)	0.0422 (6)	0.0095 (5)	0.0048 (5)	0.0015 (5)
S	0.0521 (2)	0.0410 (2)	0.03312 (18)	0.00382 (15)	0.01030 (14)	0.00021 (14)

C1—C6	1.383 (2)	C10—C15	1.381 (2)
C1—C2	1.383 (2)	C10—C11	1.397 (2)
C1—S	1.7604 (14)	C11—C12	1.379 (2)
C2—C3	1.382 (2)	C11—H11	0.9300
C2—H2	0.9300	C12—O3	1.3635 (18)
C3—C4	1.369 (3)	C12—C13	1.4062 (18)
C3—H3	0.9300	C13—O4	1.3631 (17)
C4—C5	1.378 (2)	C13—C14	1.375 (2)
C4—H4	0.9300	C14—C15	1.391 (2)
C5—C6	1.377 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—O4	1.4229 (19)
C7—N	1.4638 (19)	C16—H16A	0.9600
C7—H7A	0.9600	C16—H16B	0.9600
C7—H7B	0.9600	C16—H16C	0.9600
C7—H7C	0.9600	C17—O3	1.4173 (19)
C8—N	1.4773 (19)	C17—H17A	0.9600
C8—C9	1.519 (2)	C17—H17B	0.9600
C8—H8A	0.9700	C17—H17C	0.9600
C8—H8B	0.9700	N—S	1.6317 (12)
C9—C10	1.511 (2)	O1—S	1.4254 (13)
C9—H9A	0.9700	O2—S	1.4262 (11)
C9—H9B	0.9700
C6—C1—C2	120.38 (14)	C12—C11—C10	121.59 (13)
C6—C1—S	119.60 (11)	C12—C11—H11	119.2
C2—C1—S	119.92 (12)	C10—C11—H11	119.2
C3—C2—C1	119.37 (15)	O3—C12—C11	124.96 (12)
C3—C2—H2	120.3	O3—C12—C13	115.34 (13)
C1—C2—H2	120.3	C11—C12—C13	119.70 (13)
C4—C3—C2	120.51 (15)	O4—C13—C14	126.05 (12)
C4—C3—H3	119.7	O4—C13—C12	115.10 (12)
C2—C3—H3	119.7	C14—C13—C12	118.85 (13)
C3—C4—C5	119.85 (15)	C13—C14—C15	120.89 (13)
C3—C4—H4	120.1	C13—C14—H14	119.6
C5—C4—H4	120.1	C15—C14—H14	119.6
C6—C5—C4	120.59 (16)	C10—C15—C14	120.93 (14)
C6—C5—H5	119.7	C10—C15—H15	119.5
C4—C5—H5	119.7	C14—C15—H15	119.5
C5—C6—C1	119.30 (14)	O4—C16—H16A	109.5
C5—C6—H6	120.4	O4—C16—H16B	109.5
C1—C6—H6	120.4	H16A—C16—H16B	109.5
N—C7—H7A	109.5	O4—C16—H16C	109.5
N—C7—H7B	109.5	H16A—C16—H16C	109.5
H7A—C7—H7B	109.5	H16B—C16—H16C	109.5
N—C7—H7C	109.5	O3—C17—H17A	109.5
H7A—C7—H7C	109.5	O3—C17—H17B	109.5
H7B—C7—H7C	109.5	H17A—C17—H17B	109.5
N—C8—C9	112.04 (13)	O3—C17—H17C	109.5
N—C8—H8A	109.2	H17A—C17—H17C	109.5
C9—C8—H8A	109.2	H17B—C17—H17C	109.5
N—C8—H8B	109.2	C7—N—C8	114.72 (12)
C9—C8—H8B	109.2	C7—N—S	114.70 (11)
H8A—C8—H8B	107.9	C8—N—S	115.88 (9)
C10—C9—C8	116.64 (13)	C12—O3—C17	117.65 (13)
C10—C9—H9A	108.1	C13—O4—C16	117.44 (13)
C8—C9—H9A	108.1	O2—S—O1	119.54 (8)
C10—C9—H9B	108.1	O2—S—N	106.98 (7)
C8—C9—H9B	108.1	O1—S—N	106.87 (7)
H9A—C9—H9B	107.3	O2—S—C1	108.34 (7)
C15—C10—C11	118.04 (13)	O1—S—C1	108.16 (7)
C15—C10—C9	124.05 (14)	N—S—C1	106.21 (6)
C11—C10—C9	117.90 (13)
C6—C1—C2—C3	−0.6 (2)	C11—C10—C15—C14	0.3 (2)
S—C1—C2—C3	−177.00 (13)	C9—C10—C15—C14	−178.10 (14)
C1—C2—C3—C4	1.0 (3)	C13—C14—C15—C10	−0.1 (2)
C2—C3—C4—C5	−0.5 (3)	C9—C8—N—C7	−67.78 (17)
C3—C4—C5—C6	−0.4 (3)	C9—C8—N—S	154.94 (11)
C4—C5—C6—C1	0.8 (3)	C11—C12—O3—C17	2.8 (2)
C2—C1—C6—C5	−0.2 (2)	C13—C12—O3—C17	−177.37 (15)
S—C1—C6—C5	176.16 (12)	C14—C13—O4—C16	−7.8 (2)
N—C8—C9—C10	−62.34 (19)	C12—C13—O4—C16	171.97 (14)
C8—C9—C10—C15	−18.9 (2)	C7—N—S—O2	176.93 (11)
C8—C9—C10—C11	162.67 (14)	C8—N—S—O2	−45.78 (12)
C15—C10—C11—C12	−0.1 (2)	C7—N—S—O1	47.78 (13)
C9—C10—C11—C12	178.44 (14)	C8—N—S—O1	−174.93 (10)
C10—C11—C12—O3	179.51 (14)	C7—N—S—C1	−67.51 (12)
C10—C11—C12—C13	−0.4 (2)	C8—N—S—C1	69.77 (11)
O3—C12—C13—O4	0.95 (19)	C6—C1—S—O2	32.79 (14)
C11—C12—C13—O4	−179.17 (13)	C2—C1—S—O2	−150.81 (13)
O3—C12—C13—C14	−179.30 (13)	C6—C1—S—O1	163.73 (12)
C11—C12—C13—C14	0.6 (2)	C2—C1—S—O1	−19.87 (15)
O4—C13—C14—C15	179.37 (14)	C6—C1—S—N	−81.85 (13)
C12—C13—C14—C15	−0.3 (2)	C2—C1—S—N	94.55 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2i	0.93	2.60	3.380 (2)	142
C8—H8A···O3ii	0.97	2.71	3.620 (2)	156
C4—H4···O1iii	0.93	2.65	3.369 (2)	135
C3—H3···Cg2iv	0.93	2.91	3.661 (2)	139
C6—H6···Cg2ii	0.93	3.05	3.827 (8)	123

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the phenyl plane C10–C15.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2i	0.93	2.60	3.380 (2)	142
C8—H8A⋯O3ii	0.97	2.71	3.620 (2)	156
C4—H4⋯O1iii	0.93	2.65	3.369 (2)	135
C3—H3⋯Cg2iv	0.93	2.91	3.661 (2)	139
C6—H6⋯Cg2ii	0.93	3.05	3.827 (8)	123

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .