N-[2-(3,4-Dimeth-oxy-phenyl)eth-yl]-N-methyl-naphthalene-1-sulfonamide.

In the title compound, C(21)H(23)NO(4)S, the dihedral angle between the naphthalene residue and the benzene ring is 7.66 (3)°. In the molecule, there are some short C-H⋯O interactions. In the crystal, the structure is stabilized by weak intra-molecular C-H⋯O hydrogen bonds and the crystal structure is stabilized by weak C-H⋯O, C-H⋯π and π-π [centroid-centroid distance = 3.710 (2) Å] inter-actions.

Related literature

For biological activities of sulfonamide derivatives, see: Schultz et al. (2001 ▶); Sheppard (2006 ▶); Xiong et al. (2007 ▶). For related structures, see: Vennila, Thilagavathi et al. (2008 ▶); Vennila, Kavitha et al. (2008 ▶).

Experimental

Crystal data

C21H23NO4S

M = 385.46

Orthorhombic,

a = 10.070 (5) Å

b = 14.120 (4) Å

c = 27.229 (5) Å

V = 3872 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.19 mm−1

T = 295 K

0.34 × 0.30 × 0.28 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.937, T max = 0.948

9215 measured reflections

5239 independent reflections

3248 reflections with I > 2σ(I)

R int = 0.041

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.120

S = 1.01

5239 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.38 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/S1600536812008203/bt5826sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008203/bt5826Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008203/bt5826Isup3.cml

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

C21H23NO4S	F(000) = 1632
Mr = 385.46	Dx = 1.323 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 26403 reflections
a = 10.070 (5) Å	θ = 2.5–29.3°
b = 14.120 (4) Å	µ = 0.19 mm−1
c = 27.229 (5) Å	T = 295 K
V = 3872 (2) Å3	Block, colourless
Z = 8	0.34 × 0.30 × 0.28 mm

Bruker Kappa APEXII diffractometer	5239 independent reflections
Radiation source: fine-focus sealed tube	3248 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ω and φ scans	θmax = 29.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.937, Tmax = 0.948	k = −10→19
9215 measured reflections	l = −36→37

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0441P)2 + 1.1352P] where P = (Fo2 + 2Fc2)/3
5239 reflections	(Δ/σ)max < 0.001
247 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.92055 (17)	0.36733 (11)	0.08433 (6)	0.0419 (4)
C2	0.94855 (17)	0.35623 (11)	0.13542 (6)	0.0404 (4)
C3	0.8706 (2)	0.30395 (13)	0.16901 (7)	0.0524 (5)
H3	0.7930	0.2749	0.1583	0.063*
C4	0.9080 (2)	0.29561 (14)	0.21685 (7)	0.0623 (6)
H4	0.8551	0.2612	0.2384	0.075*
C5	1.0239 (2)	0.33759 (14)	0.23403 (7)	0.0640 (6)
H5	1.0485	0.3303	0.2667	0.077*
C6	1.1009 (2)	0.38904 (14)	0.20327 (7)	0.0583 (5)
H6	1.1779	0.4173	0.2151	0.070*
C7	1.06558 (19)	0.40032 (12)	0.15342 (6)	0.0463 (4)
C8	1.1458 (2)	0.45408 (13)	0.12135 (8)	0.0586 (5)
H8	1.2222	0.4829	0.1334	0.070*
C9	1.1141 (2)	0.46457 (14)	0.07347 (8)	0.0614 (5)
H9	1.1674	0.5012	0.0531	0.074*
C10	1.0010 (2)	0.42025 (12)	0.05468 (7)	0.0521 (5)
H10	0.9803	0.4268	0.0216	0.063*
C11	0.6973 (2)	0.13869 (18)	0.06506 (9)	0.0765 (7)
H11A	0.6656	0.1242	0.0327	0.115*
H11B	0.6282	0.1695	0.0834	0.115*
H11C	0.7224	0.0812	0.0814	0.115*
C12	0.92293 (19)	0.16608 (13)	0.03129 (6)	0.0498 (4)
H12A	0.9896	0.2153	0.0282	0.060*
H12B	0.8901	0.1516	−0.0014	0.060*
C13	0.98652 (19)	0.07800 (12)	0.05306 (6)	0.0493 (4)
H13A	0.9214	0.0274	0.0533	0.059*
H13B	1.0591	0.0583	0.0320	0.059*
C14	1.03892 (17)	0.09117 (11)	0.10439 (6)	0.0408 (4)
C15	0.98454 (18)	0.04479 (12)	0.14386 (6)	0.0481 (4)
H15	0.9130	0.0042	0.1390	0.058*
C16	1.03471 (19)	0.05758 (12)	0.19086 (6)	0.0496 (4)
H16	0.9955	0.0264	0.2172	0.059*
C17	1.14125 (18)	0.11561 (12)	0.19879 (6)	0.0432 (4)
C18	1.19942 (16)	0.16272 (12)	0.15871 (6)	0.0400 (4)
C19	1.14727 (16)	0.15094 (12)	0.11246 (6)	0.0396 (4)
H19	1.1847	0.1833	0.0861	0.048*
C20	1.1405 (3)	0.08946 (18)	0.28507 (7)	0.0775 (7)
H20A	1.0503	0.1109	0.2878	0.116*
H20B	1.1889	0.1075	0.3140	0.116*
H20C	1.1417	0.0218	0.2818	0.116*
C21	1.3788 (2)	0.25648 (17)	0.12955 (8)	0.0718 (6)
H21A	1.4030	0.2076	0.1068	0.108*
H21B	1.4575	0.2871	0.1415	0.108*
H21C	1.3233	0.3021	0.1133	0.108*
N1	0.81255 (14)	0.20151 (10)	0.06160 (5)	0.0460 (4)
O1	0.78111 (16)	0.34316 (12)	0.00575 (6)	0.0787 (5)
O2	0.66402 (14)	0.33351 (11)	0.08444 (7)	0.0782 (5)
O3	1.20031 (14)	0.13109 (10)	0.24318 (4)	0.0611 (4)
O4	1.30859 (13)	0.21602 (10)	0.16952 (5)	0.0563 (3)
S1	0.78111 (5)	0.31428 (4)	0.056242 (19)	0.05377 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0431 (9)	0.0320 (8)	0.0507 (10)	0.0023 (7)	0.0041 (8)	0.0032 (7)
C2	0.0467 (9)	0.0276 (8)	0.0469 (9)	0.0013 (7)	0.0096 (8)	−0.0001 (7)
C3	0.0557 (11)	0.0467 (11)	0.0549 (11)	−0.0065 (9)	0.0141 (9)	0.0008 (8)
C4	0.0846 (15)	0.0499 (12)	0.0524 (12)	−0.0034 (11)	0.0223 (11)	0.0054 (9)
C5	0.0966 (17)	0.0504 (12)	0.0449 (10)	0.0050 (12)	0.0016 (11)	−0.0040 (9)
C6	0.0765 (14)	0.0458 (11)	0.0526 (11)	−0.0035 (10)	−0.0043 (10)	−0.0114 (9)
C7	0.0569 (11)	0.0311 (9)	0.0510 (10)	−0.0020 (8)	0.0051 (8)	−0.0066 (7)
C8	0.0617 (12)	0.0451 (11)	0.0689 (13)	−0.0199 (9)	0.0048 (10)	−0.0040 (9)
C9	0.0691 (13)	0.0511 (12)	0.0640 (12)	−0.0204 (10)	0.0132 (11)	0.0092 (10)
C10	0.0632 (12)	0.0449 (10)	0.0484 (10)	−0.0020 (9)	0.0045 (9)	0.0100 (8)
C11	0.0538 (13)	0.0750 (16)	0.1008 (18)	−0.0260 (11)	−0.0027 (12)	−0.0060 (13)
C12	0.0542 (11)	0.0564 (11)	0.0389 (9)	−0.0039 (9)	−0.0016 (8)	−0.0026 (8)
C13	0.0562 (11)	0.0451 (10)	0.0467 (10)	−0.0019 (9)	−0.0007 (8)	−0.0122 (8)
C14	0.0465 (9)	0.0346 (8)	0.0413 (9)	0.0060 (7)	0.0008 (7)	−0.0070 (7)
C15	0.0513 (10)	0.0409 (9)	0.0521 (10)	−0.0090 (8)	−0.0017 (9)	−0.0022 (8)
C16	0.0579 (11)	0.0460 (10)	0.0447 (10)	−0.0100 (9)	0.0034 (8)	0.0051 (8)
C17	0.0489 (10)	0.0420 (9)	0.0388 (9)	−0.0004 (8)	−0.0017 (8)	−0.0016 (7)
C18	0.0384 (9)	0.0369 (9)	0.0447 (9)	0.0000 (7)	0.0020 (7)	−0.0030 (7)
C19	0.0416 (9)	0.0367 (9)	0.0405 (9)	0.0037 (7)	0.0068 (7)	−0.0008 (7)
C20	0.1034 (19)	0.0884 (16)	0.0407 (11)	−0.0257 (15)	−0.0018 (12)	0.0064 (11)
C21	0.0554 (12)	0.0881 (17)	0.0717 (14)	−0.0249 (12)	0.0095 (11)	0.0059 (12)
N1	0.0383 (7)	0.0474 (9)	0.0524 (9)	−0.0076 (6)	−0.0042 (6)	0.0007 (7)
O1	0.0816 (11)	0.0849 (11)	0.0697 (10)	−0.0032 (9)	−0.0314 (8)	0.0276 (8)
O2	0.0397 (8)	0.0758 (11)	0.1191 (14)	0.0113 (7)	0.0055 (8)	0.0047 (9)
O3	0.0721 (9)	0.0705 (9)	0.0408 (7)	−0.0192 (7)	−0.0081 (6)	0.0050 (6)
O4	0.0484 (7)	0.0687 (9)	0.0518 (7)	−0.0179 (6)	−0.0003 (6)	0.0008 (6)
S1	0.0413 (2)	0.0552 (3)	0.0648 (3)	0.0029 (2)	−0.0096 (2)	0.0108 (2)

C1—C10	1.366 (2)	C12—H12B	0.9700
C1—C2	1.428 (2)	C13—C14	1.506 (2)
C1—S1	1.7656 (19)	C13—H13A	0.9700
C2—C3	1.413 (2)	C13—H13B	0.9700
C2—C7	1.420 (2)	C14—C15	1.372 (2)
C3—C4	1.361 (3)	C14—C19	1.397 (2)
C3—H3	0.9300	C15—C16	1.388 (2)
C4—C5	1.390 (3)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.367 (2)
C5—C6	1.353 (3)	C16—H16	0.9300
C5—H5	0.9300	C17—O3	1.365 (2)
C6—C7	1.412 (3)	C17—C18	1.406 (2)
C6—H6	0.9300	C18—O4	1.364 (2)
C7—C8	1.411 (3)	C18—C19	1.375 (2)
C8—C9	1.350 (3)	C19—H19	0.9300
C8—H8	0.9300	C20—O3	1.418 (2)
C9—C10	1.396 (3)	C20—H20A	0.9600
C9—H9	0.9300	C20—H20B	0.9600
C10—H10	0.9300	C20—H20C	0.9600
C11—N1	1.464 (2)	C21—O4	1.418 (2)
C11—H11A	0.9600	C21—H21A	0.9600
C11—H11B	0.9600	C21—H21B	0.9600
C11—H11C	0.9600	C21—H21C	0.9600
C12—N1	1.472 (2)	N1—S1	1.6300 (16)
C12—C13	1.519 (2)	O1—S1	1.4341 (15)
C12—H12A	0.9700	O2—S1	1.4330 (16)
C10—C1—C2	121.23 (16)	C14—C13—H13B	108.7
C10—C1—S1	116.60 (14)	C12—C13—H13B	108.7
C2—C1—S1	122.17 (12)	H13A—C13—H13B	107.6
C3—C2—C7	117.79 (17)	C15—C14—C19	118.48 (16)
C3—C2—C1	125.33 (17)	C15—C14—C13	121.88 (16)
C7—C2—C1	116.87 (15)	C19—C14—C13	119.63 (15)
C4—C3—C2	120.74 (19)	C14—C15—C16	120.98 (17)
C4—C3—H3	119.6	C14—C15—H15	119.5
C2—C3—H3	119.6	C16—C15—H15	119.5
C3—C4—C5	121.16 (19)	C17—C16—C15	120.63 (16)
C3—C4—H4	119.4	C17—C16—H16	119.7
C5—C4—H4	119.4	C15—C16—H16	119.7
C6—C5—C4	120.11 (19)	O3—C17—C16	125.31 (16)
C6—C5—H5	119.9	O3—C17—C18	115.48 (16)
C4—C5—H5	119.9	C16—C17—C18	119.20 (16)
C5—C6—C7	120.8 (2)	O4—C18—C19	124.91 (15)
C5—C6—H6	119.6	O4—C18—C17	115.41 (15)
C7—C6—H6	119.6	C19—C18—C17	119.66 (16)
C8—C7—C6	120.76 (18)	C18—C19—C14	121.04 (15)
C8—C7—C2	119.83 (17)	C18—C19—H19	119.5
C6—C7—C2	119.41 (17)	C14—C19—H19	119.5
C9—C8—C7	121.38 (19)	O3—C20—H20A	109.5
C9—C8—H8	119.3	O3—C20—H20B	109.5
C7—C8—H8	119.3	H20A—C20—H20B	109.5
C8—C9—C10	119.84 (18)	O3—C20—H20C	109.5
C8—C9—H9	120.1	H20A—C20—H20C	109.5
C10—C9—H9	120.1	H20B—C20—H20C	109.5
C1—C10—C9	120.81 (18)	O4—C21—H21A	109.5
C1—C10—H10	119.6	O4—C21—H21B	109.5
C9—C10—H10	119.6	H21A—C21—H21B	109.5
N1—C11—H11A	109.5	O4—C21—H21C	109.5
N1—C11—H11B	109.5	H21A—C21—H21C	109.5
H11A—C11—H11B	109.5	H21B—C21—H21C	109.5
N1—C11—H11C	109.5	C11—N1—C12	115.39 (16)
H11A—C11—H11C	109.5	C11—N1—S1	116.34 (14)
H11B—C11—H11C	109.5	C12—N1—S1	115.37 (12)
N1—C12—C13	112.19 (14)	C17—O3—C20	117.45 (16)
N1—C12—H12A	109.2	C18—O4—C21	117.28 (15)
C13—C12—H12A	109.2	O2—S1—O1	117.38 (10)
N1—C12—H12B	109.2	O2—S1—N1	107.27 (9)
C13—C12—H12B	109.2	O1—S1—N1	111.32 (9)
H12A—C12—H12B	107.9	O2—S1—C1	109.99 (10)
C14—C13—C12	114.14 (14)	O1—S1—C1	107.14 (9)
C14—C13—H13A	108.7	N1—S1—C1	102.78 (8)
C12—C13—H13A	108.7
C10—C1—C2—C3	179.26 (17)	C15—C16—C17—C18	0.3 (3)
S1—C1—C2—C3	−0.5 (2)	O3—C17—C18—O4	1.2 (2)
C10—C1—C2—C7	−1.8 (2)	C16—C17—C18—O4	−177.34 (16)
S1—C1—C2—C7	178.39 (12)	O3—C17—C18—C19	179.58 (15)
C7—C2—C3—C4	−0.7 (3)	C16—C17—C18—C19	1.0 (3)
C1—C2—C3—C4	178.20 (17)	O4—C18—C19—C14	176.77 (15)
C2—C3—C4—C5	−0.4 (3)	C17—C18—C19—C14	−1.4 (2)
C3—C4—C5—C6	1.0 (3)	C15—C14—C19—C18	0.5 (2)
C4—C5—C6—C7	−0.5 (3)	C13—C14—C19—C18	−178.45 (15)
C5—C6—C7—C8	179.94 (19)	C13—C12—N1—C11	−65.3 (2)
C5—C6—C7—C2	−0.6 (3)	C13—C12—N1—S1	154.41 (12)
C3—C2—C7—C8	−179.36 (17)	C16—C17—O3—C20	−5.1 (3)
C1—C2—C7—C8	1.6 (2)	C18—C17—O3—C20	176.43 (18)
C3—C2—C7—C6	1.2 (2)	C19—C18—O4—C21	−4.9 (3)
C1—C2—C7—C6	−177.81 (16)	C17—C18—O4—C21	173.40 (17)
C6—C7—C8—C9	179.26 (19)	C11—N1—S1—O2	34.67 (17)
C2—C7—C8—C9	−0.2 (3)	C12—N1—S1—O2	174.52 (13)
C7—C8—C9—C10	−1.2 (3)	C11—N1—S1—O1	−95.00 (16)
C2—C1—C10—C9	0.5 (3)	C12—N1—S1—O1	44.86 (15)
S1—C1—C10—C9	−179.67 (15)	C11—N1—S1—C1	150.62 (15)
C8—C9—C10—C1	1.0 (3)	C12—N1—S1—C1	−69.52 (14)
N1—C12—C13—C14	−57.6 (2)	C10—C1—S1—O2	−130.70 (15)
C12—C13—C14—C15	113.75 (19)	C2—C1—S1—O2	49.10 (16)
C12—C13—C14—C19	−67.3 (2)	C10—C1—S1—O1	−2.07 (17)
C19—C14—C15—C16	0.7 (3)	C2—C1—S1—O1	177.73 (14)
C13—C14—C15—C16	179.70 (16)	C10—C1—S1—N1	115.32 (14)
C14—C15—C16—C17	−1.1 (3)	C2—C1—S1—N1	−64.88 (15)
C15—C16—C17—O3	−178.17 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2	0.93	2.53	3.132 (3)	122
C10—H10···O1	0.93	2.37	2.804 (3)	109
C11—H11B···O2	0.96	2.34	2.821 (3)	110
C4—H4···O3i	0.93	2.46	3.310 (3)	152
C8—H8···Cg3ii	0.93	2.59	3.488 (3)	163
C20—H20C···Cg2iii	0.96	2.92	3.740 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C2–C7 and C14–C19 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2	0.93	2.53	3.132 (3)	122
C10—H10⋯O1	0.93	2.37	2.804 (3)	109
C11—H11B⋯O2	0.96	2.34	2.821 (3)	110
C4—H4⋯O3i	0.93	2.46	3.310 (3)	152
C8—H8⋯Cg3ii	0.93	2.59	3.488 (3)	163
C20—H20C⋯Cg2iii	0.96	2.92	3.740 (3)	144

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