1,1',2,2'-Tetra-methyl-3,3'-(4-methoxy-benzyl-idene)di-1H-indole.

The title compound, C(28)H(28)N(2)O, was prepared by condensation of 1,2-bimethyl-indole and 4-methoxy-benzaldehyde. In the mol-ecular structure, the plane of the non-fused benzene ring is twisted with respect to the planes of the two indole ring systems, exhibiting dihedral angles of 72.04 (7) and 72.24 (7)°, while the planes of the two indole ring systems are oriented at a dihedral angle of 87.05 (5)°. Neither hydrogen bonding nor π-π stacking is observed in the crystal structure.

Related literature

For general background to the physiological properties of indole derivatives, see: Poter et al. (1977 ▶); Sundberg (1996 ▶). For related structures, see: Chang et al. (1999 ▶); Ge et al. (1999 ▶); Morris & Andersen (1990 ▶); Azizian et al. (2007 ▶); Osawa & Namiki (1983 ▶). For the synthesis, see: Deb & Bhuyan (2006 ▶).

Experimental

Crystal data

C28H28N2O

M = 408.52

Monoclinic,

a = 10.6647 (8) Å

b = 13.2088 (10) Å

c = 16.1494 (13) Å

β = 97.1740 (10)°

V = 2257.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.25 × 0.24 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

11505 measured reflections

3955 independent reflections

3196 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.139

S = 0.83

3955 reflections

285 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017759/xu2523sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017759/xu2523Isup2.hkl

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

C28H28N2O	F(000) = 872
Mr = 408.52	Dx = 1.202 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6354 reflections
a = 10.6647 (8) Å	θ = 4.9–51.2°
b = 13.2088 (10) Å	µ = 0.07 mm−1
c = 16.1494 (13) Å	T = 296 K
β = 97.174 (1)°	Prism, colorless
V = 2257.1 (3) Å3	0.25 × 0.24 × 0.21 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3196 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 25.0°, θmin = 2.0°
φ and ω scans	h = −12→12
11505 measured reflections	k = −15→15
3955 independent reflections	l = −19→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 0.83	w = 1/[σ2(Fo2) + (0.1047P)2 + 0.8752P] where P = (Fo2 + 2Fc2)/3
3955 reflections	(Δ/σ)max < 0.001
285 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.22 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
N1	0.63286 (14)	0.32330 (11)	0.89904 (8)	0.0421 (4)
N2	0.23060 (12)	0.47645 (10)	0.62297 (8)	0.0358 (3)
O1	0.73808 (18)	0.09952 (13)	0.43460 (10)	0.0827 (5)
C1	0.54764 (14)	0.35901 (11)	0.67122 (9)	0.0316 (3)
H1	0.5937	0.4226	0.6671	0.038*
C2	0.59177 (14)	0.28915 (11)	0.60516 (9)	0.0334 (4)
C3	0.72045 (16)	0.27569 (12)	0.60290 (11)	0.0403 (4)
H3	0.7776	0.3097	0.6414	0.048*
C4	0.76556 (18)	0.21341 (14)	0.54521 (12)	0.0501 (5)
H4	0.8522	0.2066	0.5446	0.060*
C5	0.6831 (2)	0.16106 (14)	0.48826 (12)	0.0529 (5)
C6	0.5550 (2)	0.17324 (15)	0.48860 (12)	0.0544 (5)
H6	0.4984	0.1387	0.4502	0.065*
C7	0.51073 (17)	0.23765 (13)	0.54694 (11)	0.0435 (4)
H7	0.4240	0.2460	0.5464	0.052*
C8	0.6598 (4)	0.0526 (3)	0.36972 (17)	0.1146 (13)
H8A	0.7107	0.0159	0.3349	0.172*
H8B	0.6113	0.1031	0.3371	0.172*
H8C	0.6036	0.0066	0.3927	0.172*
C9	0.58732 (14)	0.32027 (11)	0.75930 (9)	0.0319 (3)
C10	0.62303 (14)	0.21961 (11)	0.78731 (10)	0.0317 (3)
C11	0.63396 (15)	0.12468 (12)	0.74924 (10)	0.0373 (4)
H11	0.6147	0.1177	0.6918	0.045*
C12	0.67336 (16)	0.04226 (12)	0.79772 (11)	0.0423 (4)
H12	0.6806	−0.0203	0.7724	0.051*
C13	0.70262 (16)	0.05046 (13)	0.88377 (11)	0.0446 (4)
H13	0.7297	−0.0065	0.9148	0.054*
C14	0.69222 (16)	0.14123 (14)	0.92376 (11)	0.0428 (4)
H14	0.7117	0.1467	0.9813	0.051*
C15	0.65141 (14)	0.22480 (12)	0.87502 (10)	0.0355 (4)
C16	0.59485 (15)	0.38016 (12)	0.82871 (10)	0.0377 (4)
C17	0.6468 (2)	0.35910 (17)	0.98459 (12)	0.0627 (6)
H17A	0.6664	0.3030	1.0218	0.094*
H17B	0.5693	0.3901	0.9960	0.094*
H17C	0.7139	0.4079	0.9926	0.094*
C18	0.5666 (2)	0.49042 (14)	0.83534 (13)	0.0561 (5)
H18A	0.6390	0.5245	0.8638	0.084*
H18B	0.4958	0.4992	0.8660	0.084*
H18C	0.5467	0.5185	0.7804	0.084*
C19	0.40945 (14)	0.38686 (11)	0.65659 (9)	0.0314 (3)
C20	0.30467 (14)	0.32631 (11)	0.67439 (9)	0.0325 (4)
C21	0.29216 (16)	0.22881 (12)	0.70659 (10)	0.0395 (4)
H21	0.3633	0.1891	0.7218	0.047*
C22	0.17413 (17)	0.19248 (14)	0.71551 (11)	0.0455 (4)
H22	0.1659	0.1277	0.7368	0.055*
C23	0.06594 (17)	0.25115 (15)	0.69312 (12)	0.0484 (4)
H23	−0.0130	0.2249	0.7000	0.058*
C24	0.07467 (16)	0.34710 (14)	0.66114 (11)	0.0438 (4)
H24	0.0028	0.3859	0.6458	0.053*
C25	0.19443 (15)	0.38423 (12)	0.65254 (9)	0.0339 (4)
C26	0.36095 (14)	0.47703 (11)	0.62486 (9)	0.0322 (3)
C27	0.14395 (17)	0.55850 (14)	0.59566 (12)	0.0477 (4)
H27A	0.0825	0.5654	0.6340	0.072*
H27B	0.1018	0.5437	0.5410	0.072*
H27C	0.1904	0.6206	0.5940	0.072*
C28	0.42723 (17)	0.56692 (13)	0.59485 (11)	0.0440 (4)
H28A	0.4049	0.6263	0.6240	0.066*
H28B	0.4025	0.5756	0.5361	0.066*
H28C	0.5169	0.5566	0.6051	0.066*

	U11	U22	U33	U12	U13	U23
N1	0.0508 (8)	0.0427 (8)	0.0313 (7)	0.0060 (6)	−0.0012 (6)	−0.0044 (6)
N2	0.0330 (7)	0.0350 (7)	0.0386 (7)	0.0063 (5)	0.0018 (6)	0.0039 (6)
O1	0.1152 (14)	0.0747 (11)	0.0624 (10)	0.0308 (10)	0.0278 (9)	−0.0145 (8)
C1	0.0315 (8)	0.0275 (8)	0.0353 (8)	−0.0008 (6)	0.0018 (6)	0.0037 (6)
C2	0.0382 (9)	0.0299 (8)	0.0324 (8)	0.0016 (6)	0.0052 (6)	0.0063 (6)
C3	0.0371 (9)	0.0382 (9)	0.0457 (10)	0.0028 (7)	0.0058 (7)	0.0039 (7)
C4	0.0499 (11)	0.0477 (11)	0.0557 (11)	0.0115 (8)	0.0177 (9)	0.0075 (9)
C5	0.0758 (14)	0.0434 (10)	0.0417 (10)	0.0161 (9)	0.0160 (9)	0.0026 (8)
C6	0.0690 (13)	0.0507 (11)	0.0416 (10)	0.0012 (9)	−0.0004 (9)	−0.0076 (8)
C7	0.0432 (9)	0.0474 (10)	0.0390 (9)	0.0005 (7)	0.0012 (7)	−0.0003 (8)
C8	0.173 (3)	0.112 (2)	0.0558 (15)	0.059 (2)	0.0022 (18)	−0.0304 (16)
C9	0.0294 (7)	0.0305 (8)	0.0347 (8)	0.0012 (6)	−0.0007 (6)	0.0008 (6)
C10	0.0281 (7)	0.0323 (8)	0.0339 (8)	0.0007 (6)	0.0008 (6)	0.0018 (6)
C11	0.0414 (9)	0.0336 (8)	0.0366 (9)	0.0005 (7)	0.0037 (7)	0.0017 (7)
C12	0.0446 (9)	0.0316 (8)	0.0514 (10)	0.0054 (7)	0.0089 (8)	0.0044 (7)
C13	0.0410 (9)	0.0411 (10)	0.0516 (11)	0.0064 (7)	0.0047 (8)	0.0156 (8)
C14	0.0398 (9)	0.0508 (10)	0.0366 (9)	0.0029 (8)	−0.0005 (7)	0.0085 (8)
C15	0.0337 (8)	0.0380 (9)	0.0338 (8)	0.0024 (7)	0.0001 (6)	0.0012 (7)
C16	0.0391 (9)	0.0338 (9)	0.0391 (9)	0.0042 (7)	0.0007 (7)	−0.0020 (7)
C17	0.0839 (15)	0.0651 (13)	0.0362 (10)	0.0102 (11)	−0.0041 (10)	−0.0105 (9)
C18	0.0727 (14)	0.0391 (10)	0.0550 (12)	0.0119 (9)	0.0018 (10)	−0.0095 (9)
C19	0.0324 (8)	0.0320 (8)	0.0294 (8)	0.0011 (6)	0.0024 (6)	0.0019 (6)
C20	0.0337 (8)	0.0337 (8)	0.0295 (8)	0.0006 (6)	0.0020 (6)	0.0000 (6)
C21	0.0385 (9)	0.0373 (9)	0.0416 (9)	−0.0008 (7)	0.0011 (7)	0.0051 (7)
C22	0.0453 (10)	0.0423 (10)	0.0485 (10)	−0.0090 (8)	0.0048 (8)	0.0065 (8)
C23	0.0375 (9)	0.0545 (11)	0.0536 (11)	−0.0099 (8)	0.0079 (8)	0.0008 (9)
C24	0.0338 (9)	0.0490 (10)	0.0481 (10)	0.0024 (7)	0.0030 (7)	−0.0022 (8)
C25	0.0340 (8)	0.0365 (8)	0.0309 (8)	0.0016 (6)	0.0025 (6)	−0.0013 (6)
C26	0.0335 (8)	0.0326 (8)	0.0305 (8)	0.0023 (6)	0.0036 (6)	0.0012 (6)
C27	0.0435 (10)	0.0446 (10)	0.0535 (11)	0.0141 (8)	0.0003 (8)	0.0048 (8)
C28	0.0461 (10)	0.0368 (9)	0.0492 (10)	0.0022 (7)	0.0069 (8)	0.0103 (7)

N1—C15	1.379 (2)	C12—H12	0.9300
N1—C16	1.380 (2)	C13—C14	1.373 (3)
N1—C17	1.450 (2)	C13—H13	0.9300
N2—C25	1.381 (2)	C14—C15	1.394 (2)
N2—C26	1.3867 (19)	C14—H14	0.9300
N2—C27	1.457 (2)	C16—C18	1.494 (2)
O1—C5	1.372 (2)	C17—H17A	0.9600
O1—C8	1.401 (4)	C17—H17B	0.9600
C1—C19	1.509 (2)	C17—H17C	0.9600
C1—C9	1.521 (2)	C18—H18A	0.9600
C1—C2	1.529 (2)	C18—H18B	0.9600
C1—H1	0.9800	C18—H18C	0.9600
C2—C7	1.375 (2)	C19—C26	1.372 (2)
C2—C3	1.389 (2)	C19—C20	1.432 (2)
C3—C4	1.374 (2)	C20—C21	1.401 (2)
C3—H3	0.9300	C20—C25	1.410 (2)
C4—C5	1.377 (3)	C21—C22	1.371 (2)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.376 (3)	C22—C23	1.400 (3)
C6—C7	1.395 (3)	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.376 (3)
C7—H7	0.9300	C23—H23	0.9300
C8—H8A	0.9600	C24—C25	1.391 (2)
C8—H8B	0.9600	C24—H24	0.9300
C8—H8C	0.9600	C26—C28	1.493 (2)
C9—C16	1.366 (2)	C27—H27A	0.9600
C9—C10	1.440 (2)	C27—H27B	0.9600
C10—C11	1.408 (2)	C27—H27C	0.9600
C10—C15	1.413 (2)	C28—H28A	0.9600
C11—C12	1.376 (2)	C28—H28B	0.9600
C11—H11	0.9300	C28—H28C	0.9600
C12—C13	1.390 (3)
C15—N1—C16	108.65 (13)	N1—C15—C14	129.36 (15)
C15—N1—C17	125.05 (15)	N1—C15—C10	107.91 (13)
C16—N1—C17	126.26 (15)	C14—C15—C10	122.72 (15)
C25—N2—C26	108.65 (12)	C9—C16—N1	109.97 (14)
C25—N2—C27	124.55 (14)	C9—C16—C18	129.17 (16)
C26—N2—C27	126.80 (14)	N1—C16—C18	120.86 (15)
C5—O1—C8	118.2 (2)	N1—C17—H17A	109.5
C19—C1—C9	112.38 (12)	N1—C17—H17B	109.5
C19—C1—C2	114.70 (13)	H17A—C17—H17B	109.5
C9—C1—C2	112.06 (12)	N1—C17—H17C	109.5
C19—C1—H1	105.6	H17A—C17—H17C	109.5
C9—C1—H1	105.6	H17B—C17—H17C	109.5
C2—C1—H1	105.6	C16—C18—H18A	109.5
C7—C2—C3	117.22 (15)	C16—C18—H18B	109.5
C7—C2—C1	123.63 (14)	H18A—C18—H18B	109.5
C3—C2—C1	119.15 (14)	C16—C18—H18C	109.5
C4—C3—C2	121.69 (17)	H18A—C18—H18C	109.5
C4—C3—H3	119.2	H18B—C18—H18C	109.5
C2—C3—H3	119.2	C26—C19—C20	107.00 (13)
C5—C4—C3	120.34 (18)	C26—C19—C1	125.84 (14)
C5—C4—H4	119.8	C20—C19—C1	127.15 (13)
C3—C4—H4	119.8	C21—C20—C25	118.45 (14)
O1—C5—C4	115.59 (19)	C21—C20—C19	134.46 (14)
O1—C5—C6	125.1 (2)	C25—C20—C19	107.09 (13)
C4—C5—C6	119.35 (17)	C22—C21—C20	119.45 (16)
C5—C6—C7	119.62 (18)	C22—C21—H21	120.3
C5—C6—H6	120.2	C20—C21—H21	120.3
C7—C6—H6	120.2	C21—C22—C23	121.13 (17)
C2—C7—C6	121.77 (17)	C21—C22—H22	119.4
C2—C7—H7	119.1	C23—C22—H22	119.4
C6—C7—H7	119.1	C24—C23—C22	120.98 (16)
O1—C8—H8A	109.5	C24—C23—H23	119.5
O1—C8—H8B	109.5	C22—C23—H23	119.5
H8A—C8—H8B	109.5	C23—C24—C25	117.91 (16)
O1—C8—H8C	109.5	C23—C24—H24	121.0
H8A—C8—H8C	109.5	C25—C24—H24	121.0
H8B—C8—H8C	109.5	N2—C25—C24	130.18 (15)
C16—C9—C10	106.89 (13)	N2—C25—C20	107.76 (13)
C16—C9—C1	123.61 (14)	C24—C25—C20	122.07 (15)
C10—C9—C1	129.50 (14)	C19—C26—N2	109.49 (13)
C11—C10—C15	117.53 (14)	C19—C26—C28	129.77 (14)
C11—C10—C9	135.90 (15)	N2—C26—C28	120.74 (13)
C15—C10—C9	106.57 (13)	N2—C27—H27A	109.5
C12—C11—C10	119.50 (15)	N2—C27—H27B	109.5
C12—C11—H11	120.2	H27A—C27—H27B	109.5
C10—C11—H11	120.2	N2—C27—H27C	109.5
C11—C12—C13	121.45 (16)	H27A—C27—H27C	109.5
C11—C12—H12	119.3	H27B—C27—H27C	109.5
C13—C12—H12	119.3	C26—C28—H28A	109.5
C14—C13—C12	121.14 (16)	C26—C28—H28B	109.5
C14—C13—H13	119.4	H28A—C28—H28B	109.5
C12—C13—H13	119.4	C26—C28—H28C	109.5
C13—C14—C15	117.65 (16)	H28A—C28—H28C	109.5
C13—C14—H14	121.2	H28B—C28—H28C	109.5
C15—C14—H14	121.2