1-Benzyl-3-(1,2-diphenyl-ethen-yl)-1H-indole.

In the title compound, C(29)H(23)N, the planar [maximum deviation from the least squares plane = 0.056 (1) Å] indole ring makes dihedral angles of 83.4 (4), 69.9 (1) and 59.9 (1)°, with the least-squares planes of three benzene rings. The mol-ecular packing is stabilized by weak inter-molecular C-H⋯π inter-actions.

Related literature

For applications of heteroarenes, see: Dyker (1999 ▶); Ritleng et al. (2002 ▶). For their pharmaceutical properties and for related reactions, see: Sundberg (1996 ▶); Ferrer et al. 2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C29H23N

M = 385.48

Monoclinic,

a = 9.6513 (7) Å

b = 11.1857 (10) Å

c = 20.0026 (14) Å

β = 101.636 (4)°

V = 2115.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 298 K

0.22 × 0.19 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.985, T max = 0.989

14333 measured reflections

4736 independent reflections

1944 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.164

S = 0.96

4736 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.17 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 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶)’.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034707/jj2051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034707/jj2051Isup2.hkl

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

C29H23N	F(000) = 816
Mr = 385.48	Dx = 1.211 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1467 reflections
a = 9.6513 (7) Å	θ = 2.6–20.8°
b = 11.1857 (10) Å	µ = 0.07 mm−1
c = 20.0026 (14) Å	T = 298 K
β = 101.636 (4)°	Block, colourless
V = 2115.0 (3) Å3	0.22 × 0.19 × 0.16 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4736 independent reflections
Radiation source: fine-focus sealed tube	1944 reflections with I > 2σ(I)
graphite	Rint = 0.057
ω and φ scan	θmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→11
Tmin = 0.985, Tmax = 0.989	k = −13→13
14333 measured reflections	l = −25→20

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.069P)2] where P = (Fo2 + 2Fc2)/3
4736 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.17 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	0.8730 (2)	0.1329 (2)	0.39886 (12)	0.0542 (7)
H1	0.9018	0.1247	0.3574	0.065*
C2	0.7345 (2)	0.1302 (2)	0.40656 (12)	0.0491 (6)
C3	0.7395 (2)	0.1442 (2)	0.47796 (11)	0.0491 (6)
C4	0.6392 (3)	0.1373 (3)	0.51975 (13)	0.0663 (8)
H4	0.5440	0.1260	0.5006	0.080*
C5	0.6829 (3)	0.1474 (3)	0.58865 (14)	0.0832 (9)
H5	0.6159	0.1437	0.6161	0.100*
C6	0.8239 (3)	0.1629 (3)	0.61903 (14)	0.0806 (9)
H6	0.8494	0.1712	0.6662	0.097*
C7	0.9262 (3)	0.1662 (2)	0.58053 (13)	0.0659 (8)
H7	1.0213	0.1747	0.6006	0.079*
C8	0.8821 (2)	0.1563 (2)	0.51037 (12)	0.0503 (6)
C9	1.1159 (2)	0.1514 (2)	0.47240 (13)	0.0592 (7)
H9A	1.1458	0.1222	0.4319	0.071*
H9B	1.1524	0.0967	0.5094	0.071*
C10	1.1807 (2)	0.2726 (2)	0.49003 (12)	0.0499 (6)
C11	1.3105 (2)	0.2806 (3)	0.53319 (12)	0.0631 (7)
H11	1.3531	0.2121	0.5543	0.076*
C12	1.3780 (3)	0.3894 (4)	0.54542 (16)	0.0867 (10)
H12	1.4664	0.3936	0.5742	0.104*
C13	1.3161 (4)	0.4907 (3)	0.51563 (19)	0.0918 (11)
H13	1.3622	0.5639	0.5240	0.110*
C14	1.1867 (4)	0.4845 (3)	0.47361 (18)	0.0918 (10)
H14	1.1435	0.5535	0.4535	0.110*
C15	1.1194 (3)	0.3754 (3)	0.46090 (15)	0.0755 (8)
H15	1.0310	0.3718	0.4320	0.091*
C16	0.6105 (2)	0.1190 (2)	0.35057 (11)	0.0515 (6)
C17	0.6344 (2)	0.0550 (2)	0.28908 (11)	0.0484 (6)
C18	0.7060 (2)	−0.0527 (3)	0.29393 (13)	0.0628 (7)
H18	0.7317	−0.0892	0.3364	0.075*
C19	0.7404 (3)	−0.1075 (3)	0.23813 (16)	0.0745 (8)
H19	0.7883	−0.1801	0.2429	0.089*
C20	0.7036 (3)	−0.0545 (3)	0.17518 (16)	0.0785 (9)
H20	0.7278	−0.0905	0.1372	0.094*
C21	0.6326 (3)	0.0498 (3)	0.16852 (13)	0.0719 (8)
H21	0.6079	0.0855	0.1258	0.086*
C22	0.5959 (3)	0.1044 (3)	0.22447 (13)	0.0640 (7)
H22	0.5446	0.1753	0.2187	0.077*
C23	0.4864 (2)	0.1698 (2)	0.35701 (13)	0.0618 (7)
H23	0.4919	0.2161	0.3961	0.074*
C24	0.3455 (2)	0.1647 (3)	0.31340 (12)	0.0562 (7)
C25	0.2926 (3)	0.0713 (3)	0.27103 (15)	0.0827 (9)
H25	0.3514	0.0071	0.2668	0.099*
C26	0.1547 (3)	0.0700 (3)	0.23466 (16)	0.0942 (11)
H26	0.1217	0.0056	0.2065	0.113*
C27	0.0660 (3)	0.1649 (4)	0.24024 (17)	0.0891 (10)
H27	−0.0264	0.1660	0.2152	0.107*
C28	0.1159 (3)	0.2566 (3)	0.28288 (16)	0.0820 (9)
H28	0.0565	0.3201	0.2876	0.098*
C29	0.2521 (3)	0.2569 (3)	0.31884 (13)	0.0702 (8)
H29	0.2832	0.3207	0.3478	0.084*
N1	0.96186 (19)	0.14922 (18)	0.46014 (10)	0.0531 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0569 (15)	0.0496 (18)	0.0525 (15)	0.0052 (13)	0.0023 (12)	0.0001 (12)
C2	0.0393 (13)	0.0439 (17)	0.0594 (15)	0.0035 (11)	−0.0009 (11)	0.0010 (12)
C3	0.0490 (14)	0.0434 (17)	0.0524 (15)	0.0013 (12)	0.0046 (11)	−0.0014 (12)
C4	0.0513 (15)	0.077 (2)	0.0687 (19)	−0.0006 (14)	0.0067 (14)	−0.0074 (15)
C5	0.077 (2)	0.109 (3)	0.0635 (19)	−0.0081 (19)	0.0151 (16)	−0.0050 (18)
C6	0.088 (2)	0.094 (3)	0.0565 (17)	−0.0118 (19)	0.0061 (17)	−0.0085 (16)
C7	0.0630 (17)	0.062 (2)	0.0637 (18)	−0.0053 (14)	−0.0086 (14)	−0.0053 (14)
C8	0.0466 (14)	0.0391 (17)	0.0623 (16)	−0.0009 (12)	0.0038 (12)	−0.0002 (12)
C9	0.0430 (14)	0.0535 (19)	0.0767 (17)	0.0046 (13)	0.0018 (12)	−0.0007 (14)
C10	0.0411 (14)	0.0489 (19)	0.0594 (15)	0.0035 (13)	0.0096 (12)	0.0018 (13)
C11	0.0459 (15)	0.070 (2)	0.0721 (17)	−0.0049 (14)	0.0088 (13)	0.0033 (15)
C12	0.0548 (18)	0.106 (3)	0.097 (2)	−0.029 (2)	0.0089 (16)	−0.010 (2)
C13	0.092 (3)	0.072 (3)	0.122 (3)	−0.030 (2)	0.047 (2)	−0.017 (2)
C14	0.092 (2)	0.054 (2)	0.130 (3)	−0.001 (2)	0.025 (2)	0.009 (2)
C15	0.0668 (18)	0.057 (2)	0.096 (2)	0.0027 (17)	−0.0005 (16)	0.0042 (18)
C16	0.0485 (14)	0.0480 (17)	0.0537 (15)	0.0026 (13)	0.0001 (11)	0.0043 (13)
C17	0.0416 (13)	0.0454 (17)	0.0522 (15)	−0.0009 (12)	−0.0047 (11)	0.0038 (13)
C18	0.0595 (16)	0.058 (2)	0.0643 (17)	0.0064 (15)	−0.0043 (13)	−0.0011 (15)
C19	0.0684 (18)	0.059 (2)	0.089 (2)	0.0113 (15)	−0.0013 (17)	−0.0144 (19)
C20	0.078 (2)	0.079 (3)	0.077 (2)	−0.0152 (19)	0.0120 (16)	−0.026 (2)
C21	0.092 (2)	0.065 (2)	0.0541 (18)	−0.0093 (18)	0.0034 (15)	0.0006 (16)
C22	0.0698 (17)	0.0533 (19)	0.0616 (18)	−0.0034 (14)	−0.0040 (14)	−0.0019 (14)
C23	0.0535 (16)	0.066 (2)	0.0613 (16)	0.0058 (14)	0.0001 (12)	−0.0008 (13)
C24	0.0477 (14)	0.060 (2)	0.0586 (15)	0.0095 (14)	0.0051 (12)	0.0085 (14)
C25	0.0544 (17)	0.083 (3)	0.102 (2)	0.0073 (16)	−0.0058 (16)	−0.0126 (19)
C26	0.0613 (19)	0.097 (3)	0.113 (3)	0.000 (2)	−0.0087 (18)	−0.013 (2)
C27	0.0467 (17)	0.122 (3)	0.092 (2)	0.012 (2)	−0.0033 (16)	0.021 (2)
C28	0.057 (2)	0.090 (3)	0.097 (2)	0.0196 (18)	0.0126 (17)	0.012 (2)
C29	0.0536 (17)	0.078 (2)	0.0779 (18)	0.0092 (16)	0.0114 (14)	0.0061 (16)
N1	0.0412 (11)	0.0516 (15)	0.0620 (13)	−0.0013 (10)	0.0001 (10)	−0.0011 (10)

C1—N1	1.359 (3)	C14—H14	0.9300
C1—C2	1.377 (3)	C15—H15	0.9300
C1—H1	0.9300	C16—C23	1.355 (3)
C2—C3	1.428 (3)	C16—C17	1.481 (3)
C2—C16	1.470 (3)	C17—C18	1.382 (3)
C3—C4	1.403 (3)	C17—C22	1.386 (3)
C3—C8	1.405 (3)	C18—C19	1.372 (3)
C4—C5	1.362 (3)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.372 (4)
C5—C6	1.385 (4)	C19—H19	0.9300
C5—H5	0.9300	C20—C21	1.345 (4)
C6—C7	1.370 (3)	C20—H20	0.9300
C6—H6	0.9300	C21—C22	1.383 (4)
C7—C8	1.386 (3)	C21—H21	0.9300
C7—H7	0.9300	C22—H22	0.9300
C8—N1	1.386 (3)	C23—C24	1.461 (3)
C9—N1	1.457 (3)	C23—H23	0.9300
C9—C10	1.505 (3)	C24—C25	1.377 (4)
C9—H9A	0.9700	C24—C29	1.389 (3)
C9—H9B	0.9700	C25—C26	1.382 (3)
C10—C15	1.369 (4)	C25—H25	0.9300
C10—C11	1.373 (3)	C26—C27	1.383 (4)
C11—C12	1.379 (4)	C26—H26	0.9300
C11—H11	0.9300	C27—C28	1.359 (4)
C12—C13	1.361 (4)	C27—H27	0.9300
C12—H12	0.9300	C28—C29	1.365 (3)
C13—C14	1.359 (4)	C28—H28	0.9300
C13—H13	0.9300	C29—H29	0.9300
C14—C15	1.381 (4)
N1—C1—C2	110.6 (2)	C14—C15—H15	119.4
N1—C1—H1	124.7	C23—C16—C2	119.4 (2)
C2—C1—H1	124.7	C23—C16—C17	124.8 (2)
C1—C2—C3	105.7 (2)	C2—C16—C17	115.79 (19)
C1—C2—C16	125.2 (2)	C18—C17—C22	116.7 (2)
C3—C2—C16	129.0 (2)	C18—C17—C16	121.5 (2)
C4—C3—C8	117.4 (2)	C22—C17—C16	121.6 (2)
C4—C3—C2	134.5 (2)	C19—C18—C17	122.1 (3)
C8—C3—C2	107.75 (19)	C19—C18—H18	118.9
C5—C4—C3	119.2 (2)	C17—C18—H18	118.9
C5—C4—H4	120.4	C18—C19—C20	119.6 (3)
C3—C4—H4	120.4	C18—C19—H19	120.2
C4—C5—C6	122.0 (3)	C20—C19—H19	120.2
C4—C5—H5	119.0	C21—C20—C19	119.8 (3)
C6—C5—H5	119.0	C21—C20—H20	120.1
C7—C6—C5	120.9 (3)	C19—C20—H20	120.1
C7—C6—H6	119.6	C20—C21—C22	120.8 (3)
C5—C6—H6	119.6	C20—C21—H21	119.6
C6—C7—C8	117.3 (2)	C22—C21—H21	119.6
C6—C7—H7	121.4	C21—C22—C17	120.9 (3)
C8—C7—H7	121.4	C21—C22—H22	119.5
N1—C8—C7	129.5 (2)	C17—C22—H22	119.5
N1—C8—C3	107.19 (19)	C16—C23—C24	131.4 (2)
C7—C8—C3	123.2 (2)	C16—C23—H23	114.3
N1—C9—C10	114.6 (2)	C24—C23—H23	114.3
N1—C9—H9A	108.6	C25—C24—C29	116.5 (2)
C10—C9—H9A	108.6	C25—C24—C23	125.6 (2)
N1—C9—H9B	108.6	C29—C24—C23	117.7 (3)
C10—C9—H9B	108.6	C24—C25—C26	122.0 (3)
H9A—C9—H9B	107.6	C24—C25—H25	119.0
C15—C10—C11	118.3 (3)	C26—C25—H25	119.0
C15—C10—C9	122.3 (2)	C25—C26—C27	119.7 (3)
C11—C10—C9	119.3 (2)	C25—C26—H26	120.1
C10—C11—C12	120.5 (3)	C27—C26—H26	120.1
C10—C11—H11	119.8	C28—C27—C26	118.9 (3)
C12—C11—H11	119.8	C28—C27—H27	120.6
C13—C12—C11	120.5 (3)	C26—C27—H27	120.6
C13—C12—H12	119.7	C27—C28—C29	121.0 (3)
C11—C12—H12	119.7	C27—C28—H28	119.5
C14—C13—C12	119.7 (3)	C29—C28—H28	119.5
C14—C13—H13	120.2	C28—C29—C24	121.9 (3)
C12—C13—H13	120.2	C28—C29—H29	119.1
C13—C14—C15	119.9 (3)	C24—C29—H29	119.1
C13—C14—H14	120.0	C1—N1—C8	108.66 (18)
C15—C14—H14	120.0	C1—N1—C9	126.2 (2)
C10—C15—C14	121.1 (3)	C8—N1—C9	125.02 (19)
C10—C15—H15	119.4
N1—C1—C2—C3	−0.9 (3)	C2—C16—C17—C18	46.9 (3)
N1—C1—C2—C16	177.3 (2)	C23—C16—C17—C22	49.6 (4)
C1—C2—C3—C4	−172.3 (3)	C2—C16—C17—C22	−128.0 (2)
C16—C2—C3—C4	9.6 (5)	C22—C17—C18—C19	1.3 (4)
C1—C2—C3—C8	0.7 (3)	C16—C17—C18—C19	−173.8 (2)
C16—C2—C3—C8	−177.4 (2)	C17—C18—C19—C20	0.3 (4)
C8—C3—C4—C5	2.6 (4)	C18—C19—C20—C21	−0.9 (4)
C2—C3—C4—C5	175.2 (3)	C19—C20—C21—C22	0.0 (4)
C3—C4—C5—C6	−0.8 (5)	C20—C21—C22—C17	1.7 (4)
C4—C5—C6—C7	−1.4 (5)	C18—C17—C22—C21	−2.3 (4)
C5—C6—C7—C8	1.5 (4)	C16—C17—C22—C21	172.9 (2)
C6—C7—C8—N1	−175.4 (2)	C2—C16—C23—C24	−174.0 (2)
C6—C7—C8—C3	0.5 (4)	C17—C16—C23—C24	8.5 (4)
C4—C3—C8—N1	174.1 (2)	C16—C23—C24—C25	28.5 (4)
C2—C3—C8—N1	−0.3 (3)	C16—C23—C24—C29	−157.1 (3)
C4—C3—C8—C7	−2.6 (4)	C29—C24—C25—C26	1.3 (4)
C2—C3—C8—C7	−177.0 (2)	C23—C24—C25—C26	175.7 (3)
N1—C9—C10—C15	−36.5 (3)	C24—C25—C26—C27	0.2 (5)
N1—C9—C10—C11	148.1 (2)	C25—C26—C27—C28	−1.5 (5)
C15—C10—C11—C12	−1.4 (4)	C26—C27—C28—C29	1.2 (5)
C9—C10—C11—C12	174.2 (2)	C27—C28—C29—C24	0.3 (4)
C10—C11—C12—C13	0.9 (4)	C25—C24—C29—C28	−1.6 (4)
C11—C12—C13—C14	0.1 (5)	C23—C24—C29—C28	−176.5 (2)
C12—C13—C14—C15	−0.6 (5)	C2—C1—N1—C8	0.7 (3)
C11—C10—C15—C14	0.9 (4)	C2—C1—N1—C9	177.1 (2)
C9—C10—C15—C14	−174.6 (3)	C7—C8—N1—C1	176.2 (2)
C13—C14—C15—C10	0.1 (5)	C3—C8—N1—C1	−0.3 (3)
C1—C2—C16—C23	−149.8 (3)	C7—C8—N1—C9	−0.2 (4)
C3—C2—C16—C23	27.9 (4)	C3—C8—N1—C9	−176.7 (2)
C1—C2—C16—C17	27.9 (4)	C10—C9—N1—C1	109.4 (3)
C3—C2—C16—C17	−154.3 (2)	C10—C9—N1—C8	−74.8 (3)
C23—C16—C17—C18	−135.6 (3)

Cg1 and Cg2 are the centroids of the N1/C1/C2/C3/C8 and C17–C22 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···Cg1i	0.97	2.79	3.619 (3)	144
C28—H28···Cg2ii	0.93	2.92	3.830 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/C1/C2/C3/C8 and C17–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯Cg1i	0.97	2.79	3.619 (3)	144
C28—H28⋯Cg2ii	0.93	2.92	3.830 (3)	165

Symmetry codes: (i) ; (ii) .