5-Meth-oxy-1-(3,4,5-trimethoxy-phen-yl)-1H-indole.

The title compound, C(18)H(19)NO(4), was prepared as an indole derivative with possible anti-mitotic properties. The planes of the indole and trimethoxy-phenyl rings make a dihedral angle of 45.35 (5)° with one another. In the crystal, mol-ecules related by a twofold screw axis exhibit arene C-H⋯arene-π inter-actions which are 3.035 (1) Å in length.

Related literature

For a related structure, see: Suthar et al. (2005 ▶). For pharmaceutical applications of indoles, see: Fuwa & Sasaki (2009 ▶); Li & Martins (2003 ▶).

Experimental

Crystal data

C18H19NO4

M = 313.34

Monoclinic,

a = 19.0036 (16) Å

b = 7.3179 (14) Å

c = 23.672 (4) Å

β = 96.802 (10)°

V = 3268.8 (9) Å3

Z = 8

Cu Kα radiation

μ = 0.74 mm−1

T = 295 K

0.32 × 0.27 × 0.26 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

6084 measured reflections

2951 independent reflections

2074 reflections with I > 2σ(I)

R int = 0.026

3 standard reflections every 190 reflections intensity decay: 4%

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.110

S = 1.00

2951 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶), Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810018568/fl2291sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018568/fl2291Isup2.hkl

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

C18H19NO4	F(000) = 1328
Mr = 313.34	Dx = 1.273 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 24 reflections
a = 19.0036 (16) Å	θ = 6.4–20.8°
b = 7.3179 (14) Å	µ = 0.74 mm−1
c = 23.672 (4) Å	T = 295 K
β = 96.802 (10)°	Prism, colorless
V = 3268.8 (9) Å3	0.32 × 0.27 × 0.26 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	θmax = 67.4°, θmin = 3.8°
non–profiled ω/2θ scans	h = −22→22
6084 measured reflections	k = −8→0
2951 independent reflections	l = −28→28
2074 reflections with I > 2σ(I)	3 standard reflections every 190 reflections
Rint = 0.026	intensity decay: 4%

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0613P)2 + 0.605P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.037	(Δ/σ)max < 0.001
wR(F2) = 0.110	Δρmax = 0.16 e Å−3
S = 1.00	Δρmin = −0.16 e Å−3
2951 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
209 parameters	Extinction coefficient: 0.00188 (13)
0 restraints

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
O14	0.15356 (6)	0.12928 (15)	0.49143 (5)	0.0511 (3)
O13	0.07247 (7)	0.29172 (17)	0.40657 (5)	0.0575 (3)
O5	0.40130 (7)	0.77324 (19)	0.74372 (5)	0.0647 (4)
N	0.14855 (7)	0.67340 (19)	0.60827 (5)	0.0451 (3)
O12	0.02905 (7)	0.64188 (17)	0.41594 (5)	0.0562 (4)
C11	0.08846 (8)	0.6630 (2)	0.51210 (7)	0.0459 (4)
H15	0.0741	0.7834	0.5159	0.055*
C15	0.15105 (8)	0.3970 (2)	0.55189 (6)	0.0429 (4)
H11	0.1773	0.3391	0.5824	0.051*
C14	0.13334 (8)	0.3050 (2)	0.50087 (7)	0.0414 (4)
C8	0.21611 (9)	0.6831 (2)	0.63793 (6)	0.0428 (4)
C7	0.27934 (9)	0.6005 (2)	0.62755 (7)	0.0488 (4)
H4	0.2813	0.5235	0.5965	0.059*
C13	0.09214 (8)	0.3894 (2)	0.45562 (6)	0.0430 (4)
C12	0.06941 (8)	0.5691 (2)	0.46185 (7)	0.0435 (4)
C10	0.12910 (8)	0.5758 (2)	0.55666 (6)	0.0427 (4)
C6	0.33859 (10)	0.6368 (3)	0.66472 (7)	0.0519 (4)
H3	0.3813	0.5823	0.6589	0.062*
C5	0.33640 (10)	0.7540 (2)	0.71127 (7)	0.0496 (4)
C3	0.14176 (10)	0.8679 (2)	0.68041 (7)	0.0539 (5)
H9	0.124	0.95	0.7052	0.065*
C18	0.20053 (9)	0.0443 (2)	0.53514 (7)	0.0532 (4)
H18A	0.2109	−0.0777	0.5237	0.08*
H18B	0.1786	0.04	0.5696	0.08*
H18C	0.2437	0.1134	0.5415	0.08*
C4	0.27495 (10)	0.8393 (2)	0.72137 (7)	0.0520 (4)
H7	0.274	0.9179	0.7521	0.062*
C2	0.10450 (10)	0.7872 (2)	0.63464 (7)	0.0512 (4)
H8	0.0566	0.8057	0.6228	0.061*
C9	0.21305 (9)	0.8044 (2)	0.68373 (7)	0.0466 (4)
C16	0.00926 (10)	0.8294 (3)	0.41920 (8)	0.0597 (5)
H16A	−0.0187	0.8644	0.3844	0.09*
H16B	0.0511	0.9038	0.4248	0.09*
H16C	−0.0179	0.8461	0.4505	0.09*
C17	0.10615 (13)	0.3480 (3)	0.35877 (8)	0.0751 (6)
H17A	0.0895	0.2739	0.3265	0.113*
H17B	0.1565	0.3342	0.3673	0.113*
H17C	0.0951	0.4738	0.3504	0.113*
C19	0.40555 (13)	0.8959 (3)	0.78968 (9)	0.0857 (7)
H1A	0.4531	0.8973	0.8086	0.129*
H1B	0.3736	0.858	0.8159	0.129*
H1C	0.3929	1.0162	0.7759	0.129*

	U11	U22	U33	U12	U13	U23
O14	0.0641 (7)	0.0342 (6)	0.0528 (7)	0.0029 (5)	−0.0026 (6)	−0.0024 (5)
O13	0.0760 (8)	0.0458 (7)	0.0466 (6)	−0.0098 (6)	−0.0091 (6)	−0.0038 (5)
O5	0.0659 (8)	0.0628 (9)	0.0605 (8)	−0.0043 (7)	−0.0125 (6)	−0.0102 (7)
N	0.0516 (8)	0.0402 (8)	0.0423 (7)	0.0020 (6)	0.0006 (6)	−0.0044 (6)
O12	0.0620 (8)	0.0452 (7)	0.0560 (7)	0.0041 (6)	−0.0155 (6)	0.0022 (6)
C11	0.0497 (9)	0.0362 (9)	0.0503 (9)	0.0013 (7)	0.0003 (7)	−0.0013 (7)
C15	0.0465 (9)	0.0387 (9)	0.0420 (8)	−0.0023 (7)	−0.0006 (7)	0.0026 (7)
C14	0.0443 (8)	0.0322 (8)	0.0475 (8)	−0.0049 (7)	0.0050 (7)	0.0006 (7)
C8	0.0522 (9)	0.0359 (9)	0.0394 (8)	−0.0001 (7)	0.0009 (7)	−0.0006 (7)
C7	0.0568 (10)	0.0445 (10)	0.0446 (8)	0.0004 (8)	0.0043 (7)	−0.0065 (7)
C13	0.0468 (9)	0.0386 (9)	0.0421 (8)	−0.0093 (7)	−0.0016 (7)	−0.0018 (7)
C12	0.0409 (8)	0.0398 (9)	0.0480 (9)	−0.0034 (7)	−0.0027 (7)	0.0044 (7)
C10	0.0458 (8)	0.0383 (9)	0.0431 (8)	−0.0040 (7)	0.0021 (7)	−0.0025 (7)
C6	0.0531 (10)	0.0494 (10)	0.0528 (10)	0.0010 (8)	0.0044 (8)	−0.0033 (8)
C5	0.0589 (10)	0.0424 (10)	0.0452 (9)	−0.0040 (8)	−0.0040 (8)	0.0020 (7)
C3	0.0648 (11)	0.0459 (10)	0.0505 (9)	0.0095 (8)	0.0050 (8)	−0.0088 (8)
C18	0.0551 (10)	0.0418 (10)	0.0619 (10)	0.0023 (8)	0.0034 (8)	0.0063 (8)
C4	0.0704 (12)	0.0417 (10)	0.0423 (8)	−0.0013 (9)	−0.0001 (8)	−0.0072 (7)
C2	0.0560 (10)	0.0448 (9)	0.0523 (9)	0.0092 (8)	0.0044 (8)	−0.0017 (8)
C9	0.0608 (10)	0.0371 (9)	0.0409 (8)	0.0014 (8)	0.0022 (7)	−0.0016 (7)
C16	0.0653 (12)	0.0456 (11)	0.0654 (12)	0.0073 (9)	−0.0046 (9)	0.0097 (9)
C17	0.1107 (18)	0.0663 (14)	0.0487 (10)	0.0058 (13)	0.0109 (11)	−0.0032 (10)
C19	0.0995 (17)	0.0828 (17)	0.0663 (13)	0.0018 (14)	−0.0254 (12)	−0.0217 (12)

O14—C14	1.368 (2)	C13—C12	1.397 (2)
O14—C18	1.427 (2)	C6—C5	1.401 (2)
O13—C13	1.3769 (18)	C6—H3	0.93
O13—C17	1.425 (2)	C5—C4	1.370 (2)
O5—C5	1.381 (2)	C3—C2	1.357 (2)
O5—C19	1.405 (2)	C3—C9	1.426 (2)
N—C2	1.381 (2)	C3—H9	0.93
N—C8	1.390 (2)	C18—H18A	0.96
N—C10	1.4255 (19)	C18—H18B	0.96
O12—C12	1.3622 (18)	C18—H18C	0.96
O12—C16	1.427 (2)	C4—C9	1.412 (2)
C11—C12	1.384 (2)	C4—H7	0.93
C11—C10	1.387 (2)	C2—H8	0.93
C11—H15	0.93	C16—H16A	0.96
C15—C10	1.382 (2)	C16—H16B	0.96
C15—C14	1.389 (2)	C16—H16C	0.96
C15—H11	0.93	C17—H17A	0.96
C14—C13	1.394 (2)	C17—H17B	0.96
C8—C7	1.393 (2)	C17—H17C	0.96
C8—C9	1.408 (2)	C19—H1A	0.96
C7—C6	1.371 (2)	C19—H1B	0.96
C7—H4	0.93	C19—H1C	0.96
C14—O14—C18	117.06 (12)	C2—C3—C9	107.72 (15)
C13—O13—C17	114.63 (14)	C2—C3—H9	126.1
C5—O5—C19	117.49 (16)	C9—C3—H9	126.1
C2—N—C8	108.29 (13)	O14—C18—H18A	109.5
C2—N—C10	125.44 (14)	O14—C18—H18B	109.5
C8—N—C10	126.06 (14)	H18A—C18—H18B	109.5
C12—O12—C16	117.38 (13)	O14—C18—H18C	109.5
C12—C11—C10	119.38 (15)	H18A—C18—H18C	109.5
C12—C11—H15	120.3	H18B—C18—H18C	109.5
C10—C11—H15	120.3	C5—C4—C9	118.11 (15)
C10—C15—C14	119.05 (15)	C5—C4—H7	120.9
C10—C15—H11	120.5	C9—C4—H7	120.9
C14—C15—H11	120.5	C3—C2—N	109.65 (16)
O14—C14—C15	123.64 (14)	C3—C2—H8	125.2
O14—C14—C13	115.72 (14)	N—C2—H8	125.2
C15—C14—C13	120.63 (15)	C8—C9—C4	119.51 (16)
N—C8—C7	130.78 (15)	C8—C9—C3	106.80 (15)
N—C8—C9	107.54 (14)	C4—C9—C3	133.69 (16)
C7—C8—C9	121.66 (15)	O12—C16—H16A	109.5
C6—C7—C8	117.58 (16)	O12—C16—H16B	109.5
C6—C7—H4	121.2	H16A—C16—H16B	109.5
C8—C7—H4	121.2	O12—C16—H16C	109.5
O13—C13—C14	119.30 (15)	H16A—C16—H16C	109.5
O13—C13—C12	121.42 (14)	H16B—C16—H16C	109.5
C14—C13—C12	119.23 (14)	O13—C17—H17A	109.5
O12—C12—C11	123.83 (15)	O13—C17—H17B	109.5
O12—C12—C13	115.82 (14)	H17A—C17—H17B	109.5
C11—C12—C13	120.35 (15)	O13—C17—H17C	109.5
C15—C10—C11	121.32 (15)	H17A—C17—H17C	109.5
C15—C10—N	119.60 (14)	H17B—C17—H17C	109.5
C11—C10—N	119.08 (15)	O5—C19—H1A	109.5
C7—C6—C5	121.68 (17)	O5—C19—H1B	109.5
C7—C6—H3	119.2	H1A—C19—H1B	109.5
C5—C6—H3	119.2	O5—C19—H1C	109.5
C4—C5—O5	125.46 (16)	H1A—C19—H1C	109.5
C4—C5—C6	121.44 (16)	H1B—C19—H1C	109.5
O5—C5—C6	113.10 (16)

H··· ring-centroid distance	Angle between the H···ring-centroid line and the aromatic ring normal
3.035 (1) Å	5.6 (3) °