5-Meth-oxy-3-[(5-meth-oxy-1H-indol-3-yl)(phen-yl)meth-yl]-1H-indole.

In the title compound, C(25)H(22)N(2)O(2), the indole rings are individually almost planar [with maximum deviations of 0.0116 (19) and 0.0113 (18) Å] and are almost orthogonal to each other, making a dihedral angle of 84.49 (6)°. The benzene ring is inclined at 72.83 (9) and 80.85 (9)° with respect to the indole rings. In the crystal, mol-ecules are linked by N-H⋯O inter-actions into chains running parallel to the c axis. The crystal structure is further stabilized by C-H⋯π inter-actions.

Related literature

For the biological activity and uses of indole derivatives, see: Bell et al. (1994 ▶); Ge et al. (1996 ▶). For related structures, see: Zhang et al. (2006 ▶, 2007 ▶).

Experimental

Crystal data

C25H22N2O2

M = 382.45

Monoclinic,

a = 9.1545 (4) Å

b = 10.5954 (6) Å

c = 21.1668 (13) Å

β = 93.679 (2)°

V = 2048.86 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEXII KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.981, T max = 0.988

16790 measured reflections

3087 independent reflections

2317 reflections with I > 2σ(I)

R int = 0.034

θmax = 23.7°

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.119

S = 1.03

3087 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811045491/pv2461sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045491/pv2461Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045491/pv2461Isup3.cml

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

C25H22N2O2	F(000) = 808
Mr = 382.45	Dx = 1.240 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3087 reflections
a = 9.1545 (4) Å	θ = 2.2–23.7°
b = 10.5954 (6) Å	µ = 0.08 mm−1
c = 21.1668 (13) Å	T = 293 K
β = 93.679 (2)°	Block, brown
V = 2048.86 (19) Å3	0.25 × 0.20 × 0.15 mm
Z = 4

Bruker APEXII KappaCCD diffractometer	3087 independent reflections
Radiation source: fine-focus sealed tube	2317 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω and φ scans	θmax = 23.7°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −7→10
Tmin = 0.981, Tmax = 0.988	k = −11→11
16790 measured reflections	l = −22→23

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0627P)2 + 0.4003P] where P = (Fo2 + 2Fc2)/3
3087 reflections	(Δ/σ)max < 0.001
264 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.18 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.

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	0.4797 (2)	0.37371 (19)	0.41816 (10)	0.0532 (5)
H1	0.5236	0.4447	0.4370	0.064*
C2	0.3360 (2)	0.3804 (2)	0.39415 (11)	0.0661 (6)
H2	0.2837	0.4552	0.3973	0.079*
C3	0.2704 (2)	0.2767 (3)	0.36573 (12)	0.0748 (7)
H3	0.1739	0.2812	0.3493	0.090*
C4	0.3477 (2)	0.1667 (3)	0.36166 (12)	0.0776 (8)
H4	0.3033	0.0962	0.3426	0.093*
C5	0.4916 (2)	0.1600 (2)	0.38590 (10)	0.0580 (6)
H5	0.5433	0.0850	0.3827	0.070*
C6	0.55940 (18)	0.26319 (17)	0.41470 (8)	0.0405 (5)
C7	0.71658 (18)	0.25468 (16)	0.44225 (8)	0.0374 (4)
H7	0.7559	0.1752	0.4268	0.045*
C8	0.72666 (19)	0.24617 (17)	0.51335 (8)	0.0394 (4)
C9	0.6212 (2)	0.26862 (18)	0.55446 (9)	0.0493 (5)
H9	0.5270	0.2967	0.5429	0.059*
C10	0.85246 (19)	0.20426 (17)	0.55141 (8)	0.0402 (4)
C11	0.8153 (2)	0.20311 (18)	0.61463 (9)	0.0489 (5)
C12	0.9142 (3)	0.1637 (2)	0.66314 (10)	0.0639 (6)
H12	0.8885	0.1626	0.7049	0.077*
C13	1.0503 (3)	0.1267 (2)	0.64757 (11)	0.0681 (6)
H13	1.1183	0.1007	0.6795	0.082*
C14	1.0901 (2)	0.1267 (2)	0.58488 (11)	0.0566 (6)
C15	0.9929 (2)	0.16574 (17)	0.53660 (9)	0.0460 (5)
H15	1.0197	0.1666	0.4950	0.055*
C16	1.2814 (2)	0.0968 (2)	0.51545 (13)	0.0767 (7)
H16A	1.2214	0.0460	0.4866	0.115*
H16B	1.3809	0.0682	0.5160	0.115*
H16C	1.2763	0.1834	0.5020	0.115*
C17	0.80985 (17)	0.35843 (17)	0.41750 (8)	0.0378 (4)
C18	0.8511 (2)	0.46889 (19)	0.44561 (9)	0.0502 (5)
H18	0.8282	0.4933	0.4860	0.060*
C19	0.94249 (19)	0.47413 (18)	0.35062 (9)	0.0445 (5)
C20	0.86769 (17)	0.35972 (16)	0.35638 (8)	0.0365 (4)
C21	0.86324 (18)	0.27284 (18)	0.30657 (8)	0.0422 (5)
H21	0.8142	0.1964	0.3095	0.051*
C22	0.9332 (2)	0.30362 (19)	0.25334 (9)	0.0468 (5)
C23	1.0038 (2)	0.4195 (2)	0.24795 (10)	0.0566 (6)
H23	1.0473	0.4387	0.2106	0.068*
C24	1.0106 (2)	0.5050 (2)	0.29604 (10)	0.0571 (6)
H24	1.0592	0.5815	0.2924	0.069*
C25	0.8751 (4)	0.1091 (3)	0.20263 (14)	0.1214 (14)
H25A	0.9235	0.0574	0.2348	0.182*
H25B	0.8804	0.0692	0.1621	0.182*
H25C	0.7744	0.1199	0.2116	0.182*
N1	0.6733 (2)	0.24406 (16)	0.61507 (8)	0.0585 (5)
H1A	0.6248	0.2529	0.6483	0.070*
N2	0.93115 (18)	0.53917 (16)	0.40619 (8)	0.0568 (5)
H2A	0.9683	0.6122	0.4148	0.068*
O1	1.23040 (17)	0.08657 (16)	0.57707 (8)	0.0778 (5)
O2	0.94253 (17)	0.22539 (15)	0.20173 (7)	0.0693 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0506 (12)	0.0478 (13)	0.0616 (14)	0.0015 (10)	0.0059 (10)	−0.0035 (10)
C2	0.0535 (13)	0.0641 (16)	0.0804 (17)	0.0134 (11)	0.0026 (11)	−0.0016 (13)
C3	0.0444 (12)	0.092 (2)	0.0867 (18)	0.0084 (13)	−0.0066 (11)	−0.0137 (15)
C4	0.0510 (13)	0.0825 (19)	0.097 (2)	−0.0035 (13)	−0.0095 (12)	−0.0342 (15)
C5	0.0470 (11)	0.0568 (14)	0.0701 (15)	0.0024 (10)	0.0022 (10)	−0.0191 (11)
C6	0.0387 (10)	0.0447 (12)	0.0390 (11)	−0.0023 (8)	0.0090 (8)	−0.0032 (8)
C7	0.0385 (9)	0.0368 (10)	0.0376 (11)	−0.0013 (8)	0.0088 (8)	−0.0050 (8)
C8	0.0442 (10)	0.0363 (11)	0.0390 (11)	−0.0053 (8)	0.0115 (8)	−0.0025 (8)
C9	0.0522 (11)	0.0499 (12)	0.0472 (13)	−0.0019 (9)	0.0134 (10)	−0.0004 (9)
C10	0.0504 (11)	0.0320 (10)	0.0387 (11)	−0.0068 (8)	0.0072 (8)	−0.0012 (8)
C11	0.0643 (13)	0.0415 (12)	0.0419 (12)	−0.0069 (10)	0.0118 (10)	0.0000 (9)
C12	0.0972 (18)	0.0559 (14)	0.0384 (12)	−0.0070 (13)	0.0021 (12)	0.0074 (10)
C13	0.0833 (17)	0.0560 (15)	0.0626 (16)	0.0029 (12)	−0.0130 (13)	0.0122 (12)
C14	0.0611 (13)	0.0438 (13)	0.0641 (15)	−0.0001 (10)	−0.0033 (11)	0.0032 (10)
C15	0.0514 (11)	0.0403 (11)	0.0464 (12)	−0.0042 (9)	0.0046 (9)	−0.0017 (9)
C16	0.0547 (13)	0.0661 (17)	0.111 (2)	0.0008 (11)	0.0160 (14)	0.0084 (15)
C17	0.0364 (9)	0.0403 (11)	0.0372 (11)	−0.0024 (8)	0.0056 (8)	−0.0028 (8)
C18	0.0574 (12)	0.0516 (13)	0.0427 (11)	−0.0084 (10)	0.0122 (9)	−0.0075 (10)
C19	0.0474 (10)	0.0405 (11)	0.0463 (12)	−0.0032 (9)	0.0079 (9)	0.0011 (9)
C20	0.0341 (9)	0.0378 (11)	0.0379 (11)	−0.0009 (8)	0.0047 (7)	0.0008 (8)
C21	0.0402 (10)	0.0454 (12)	0.0418 (11)	−0.0063 (8)	0.0089 (8)	−0.0014 (9)
C22	0.0490 (11)	0.0546 (13)	0.0379 (11)	−0.0024 (9)	0.0112 (9)	−0.0024 (10)
C23	0.0662 (13)	0.0579 (14)	0.0483 (13)	−0.0051 (11)	0.0236 (10)	0.0102 (11)
C24	0.0662 (13)	0.0416 (13)	0.0659 (15)	−0.0092 (10)	0.0223 (11)	0.0068 (11)
C25	0.167 (3)	0.118 (3)	0.086 (2)	−0.081 (2)	0.067 (2)	−0.0612 (19)
N1	0.0740 (12)	0.0639 (12)	0.0403 (11)	−0.0035 (9)	0.0243 (9)	−0.0015 (8)
N2	0.0704 (11)	0.0422 (10)	0.0591 (11)	−0.0166 (8)	0.0140 (9)	−0.0078 (9)
O1	0.0604 (10)	0.0750 (12)	0.0961 (14)	0.0174 (8)	−0.0089 (9)	0.0057 (9)
O2	0.0840 (11)	0.0779 (11)	0.0491 (9)	−0.0194 (9)	0.0296 (8)	−0.0157 (8)

C1—C2	1.382 (3)	C14—C15	1.374 (3)
C1—C6	1.384 (3)	C15—H15	0.9300
C1—H1	0.9300	C16—O1	1.417 (3)
C2—C3	1.372 (3)	C16—H16A	0.9600
C2—H2	0.9300	C16—H16B	0.9600
C3—C4	1.369 (3)	C16—H16C	0.9600
C3—H3	0.9300	C17—C18	1.356 (3)
C4—C5	1.385 (3)	C17—C20	1.429 (2)
C4—H4	0.9300	C18—N2	1.366 (2)
C5—C6	1.379 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—N2	1.373 (2)
C6—C7	1.520 (2)	C19—C24	1.386 (3)
C7—C8	1.505 (2)	C19—C20	1.401 (2)
C7—C17	1.506 (2)	C20—C21	1.398 (2)
C7—H7	0.9800	C21—C22	1.371 (3)
C8—C9	1.362 (3)	C21—H21	0.9300
C8—C10	1.433 (3)	C22—O2	1.378 (2)
C9—N1	1.365 (3)	C22—C23	1.395 (3)
C9—H9	0.9300	C23—C24	1.361 (3)
C10—C11	1.402 (3)	C23—H23	0.9300
C10—C15	1.404 (3)	C24—H24	0.9300
C11—N1	1.371 (3)	C25—O2	1.379 (3)
C11—C12	1.389 (3)	C25—H25A	0.9600
C12—C13	1.367 (3)	C25—H25B	0.9600
C12—H12	0.9300	C25—H25C	0.9600
C13—C14	1.398 (3)	N1—H1A	0.8600
C13—H13	0.9300	N2—H2A	0.8600
C14—O1	1.373 (2)
C2—C1—C6	121.1 (2)	C14—C15—H15	120.7
C2—C1—H1	119.4	C10—C15—H15	120.7
C6—C1—H1	119.4	O1—C16—H16A	109.5
C3—C2—C1	120.0 (2)	O1—C16—H16B	109.5
C3—C2—H2	120.0	H16A—C16—H16B	109.5
C1—C2—H2	120.0	O1—C16—H16C	109.5
C4—C3—C2	119.8 (2)	H16A—C16—H16C	109.5
C4—C3—H3	120.1	H16B—C16—H16C	109.5
C2—C3—H3	120.1	C18—C17—C20	106.26 (15)
C3—C4—C5	120.2 (2)	C18—C17—C7	128.73 (16)
C3—C4—H4	119.9	C20—C17—C7	124.96 (15)
C5—C4—H4	119.9	C17—C18—N2	110.36 (17)
C6—C5—C4	120.9 (2)	C17—C18—H18	124.8
C6—C5—H5	119.5	N2—C18—H18	124.8
C4—C5—H5	119.5	N2—C19—C24	131.17 (18)
C5—C6—C1	118.03 (17)	N2—C19—C20	107.18 (15)
C5—C6—C7	120.69 (17)	C24—C19—C20	121.65 (18)
C1—C6—C7	121.27 (17)	C21—C20—C19	119.64 (16)
C8—C7—C17	113.07 (14)	C21—C20—C17	132.98 (16)
C8—C7—C6	112.52 (14)	C19—C20—C17	107.37 (15)
C17—C7—C6	111.53 (15)	C22—C21—C20	118.07 (17)
C8—C7—H7	106.4	C22—C21—H21	121.0
C17—C7—H7	106.4	C20—C21—H21	121.0
C6—C7—H7	106.4	C21—C22—O2	124.35 (18)
C9—C8—C10	105.80 (17)	C21—C22—C23	121.32 (18)
C9—C8—C7	128.92 (17)	O2—C22—C23	114.32 (17)
C10—C8—C7	125.19 (15)	C24—C23—C22	121.57 (18)
C8—C9—N1	110.34 (18)	C24—C23—H23	119.2
C8—C9—H9	124.8	C22—C23—H23	119.2
N1—C9—H9	124.8	C23—C24—C19	117.70 (19)
C11—C10—C15	119.51 (18)	C23—C24—H24	121.2
C11—C10—C8	107.68 (16)	C19—C24—H24	121.2
C15—C10—C8	132.80 (17)	O2—C25—H25A	109.5
N1—C11—C12	131.56 (19)	O2—C25—H25B	109.5
N1—C11—C10	106.98 (17)	H25A—C25—H25B	109.5
C12—C11—C10	121.46 (19)	O2—C25—H25C	109.5
C13—C12—C11	118.0 (2)	H25A—C25—H25C	109.5
C13—C12—H12	121.0	H25B—C25—H25C	109.5
C11—C12—H12	121.0	C9—N1—C11	109.19 (16)
C12—C13—C14	121.7 (2)	C9—N1—H1A	125.4
C12—C13—H13	119.2	C11—N1—H1A	125.4
C14—C13—H13	119.2	C18—N2—C19	108.83 (16)
O1—C14—C15	124.7 (2)	C18—N2—H2A	125.6
O1—C14—C13	114.60 (19)	C19—N2—H2A	125.6
C15—C14—C13	120.7 (2)	C14—O1—C16	116.91 (17)
C14—C15—C10	118.66 (19)	C22—O2—C25	118.42 (16)
C6—C1—C2—C3	−0.7 (3)	C8—C10—C15—C14	−178.15 (19)
C1—C2—C3—C4	0.4 (4)	C8—C7—C17—C18	−28.6 (3)
C2—C3—C4—C5	−0.2 (4)	C6—C7—C17—C18	99.3 (2)
C3—C4—C5—C6	0.3 (4)	C8—C7—C17—C20	154.25 (16)
C4—C5—C6—C1	−0.5 (3)	C6—C7—C17—C20	−77.8 (2)
C4—C5—C6—C7	178.92 (19)	C20—C17—C18—N2	−0.1 (2)
C2—C1—C6—C5	0.7 (3)	C7—C17—C18—N2	−177.62 (17)
C2—C1—C6—C7	−178.74 (18)	N2—C19—C20—C21	−179.02 (16)
C5—C6—C7—C8	−104.3 (2)	C24—C19—C20—C21	1.2 (3)
C1—C6—C7—C8	75.1 (2)	N2—C19—C20—C17	0.3 (2)
C5—C6—C7—C17	127.43 (19)	C24—C19—C20—C17	−179.42 (17)
C1—C6—C7—C17	−53.1 (2)	C18—C17—C20—C21	179.09 (19)
C17—C7—C8—C9	113.9 (2)	C7—C17—C20—C21	−3.3 (3)
C6—C7—C8—C9	−13.6 (3)	C18—C17—C20—C19	−0.2 (2)
C17—C7—C8—C10	−70.0 (2)	C7—C17—C20—C19	177.49 (16)
C6—C7—C8—C10	162.53 (17)	C19—C20—C21—C22	0.0 (3)
C10—C8—C9—N1	0.3 (2)	C17—C20—C21—C22	−179.20 (18)
C7—C8—C9—N1	176.99 (16)	C20—C21—C22—O2	177.46 (17)
C9—C8—C10—C11	0.2 (2)	C20—C21—C22—C23	−1.7 (3)
C7—C8—C10—C11	−176.63 (16)	C21—C22—C23—C24	2.3 (3)
C9—C8—C10—C15	179.1 (2)	O2—C22—C23—C24	−176.93 (19)
C7—C8—C10—C15	2.2 (3)	C22—C23—C24—C19	−1.1 (3)
C15—C10—C11—N1	−179.67 (17)	N2—C19—C24—C23	179.6 (2)
C8—C10—C11—N1	−0.7 (2)	C20—C19—C24—C23	−0.7 (3)
C15—C10—C11—C12	−0.5 (3)	C8—C9—N1—C11	−0.7 (2)
C8—C10—C11—C12	178.51 (18)	C12—C11—N1—C9	−178.2 (2)
N1—C11—C12—C13	179.5 (2)	C10—C11—N1—C9	0.9 (2)
C10—C11—C12—C13	0.5 (3)	C17—C18—N2—C19	0.3 (2)
C11—C12—C13—C14	−0.6 (3)	C24—C19—N2—C18	179.3 (2)
C12—C13—C14—O1	−179.8 (2)	C20—C19—N2—C18	−0.4 (2)
C12—C13—C14—C15	0.7 (3)	C15—C14—O1—C16	5.7 (3)
O1—C14—C15—C10	179.89 (18)	C13—C14—O1—C16	−173.79 (19)
C13—C14—C15—C10	−0.7 (3)	C21—C22—O2—C25	1.3 (3)
C11—C10—C15—C14	0.6 (3)	C23—C22—O2—C25	−179.6 (2)

Cg2, Cg3, Cg4 and Cg5 are the centroids of the N2/C17–C20, C1–C6, C10–C15 and C19–C24 rings, respectively

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.09	2.904 (2)	158
C25—H25B···Cg2ii	0.96	2.95	3.515 (3)	119
C16—H16C···Cg3iii	0.96	2.90	3.508 (3)	122
N2—H2A···Cg4iv	0.86	2.49	3.3149 (19)	160
C3—H3···Cg5v	0.93	2.60	3.470 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg2, Cg3, Cg4 and Cg5 are the centroids of the N2/C17–C20, C1–C6, C10–C15 and C19–C24 rings, respectively

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.09	2.904 (2)	158
C25—H25B⋯Cg2ii	0.96	2.95	3.515 (3)	119
C16—H16C⋯Cg3iii	0.96	2.90	3.508 (3)	122
N2—H2A⋯Cg4iv	0.86	2.49	3.3149 (19)	160
C3—H3⋯Cg5v	0.93	2.60	3.470 (2)	157

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