4-[Bis(1H-indol-3-yl)meth-yl]benzonitrile.

In the title mol-ecule, C(24)H(17)N(3), the didhedral angles formed by the mean planes of the indole ring systems and the benzene ring are 86.44 (7) and 86.96 (7)°. The dihedral angle between the two indole ring systems is 72.08 (6)°. In the crystal, inter-molecular bifurcated (N-H)(2)⋯N hydrogen bonds link mol-ecules into sheets lying parallel to (010).

Related literature

For background and the biological activity of bis­indolylalkanes and their derivatives, see: Bell et al. (1994 ▶). For related structures, see: Govindasamy et al. (1998 ▶); Krishna, Velmurugan, Babu & Perumal (1999 ▶); Krishna, Velmurugan & Shanmuga Sundara (1999 ▶); Seetharaman & Rajan (1995 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C24H17N3

M = 347.41

Monoclinic,

a = 9.5882 (12) Å

b = 19.155 (3) Å

c = 10.3801 (13) Å

β = 100.562 (3)°

V = 1874.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.20 × 0.15 × 0.09 mm

Data collection

Bruker SMART CCD diffractometer

14081 measured reflections

3292 independent reflections

2613 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 1.05

3292 reflections

253 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020411/lh5252sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020411/lh5252Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020411/lh5252Isup3.cml

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

C24H17N3	F(000) = 728
Mr = 347.41	Dx = 1.231 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3543 reflections
a = 9.5882 (12) Å	θ = 2.9–24.6°
b = 19.155 (3) Å	µ = 0.07 mm−1
c = 10.3801 (13) Å	T = 296 K
β = 100.562 (3)°	Block, colourless
V = 1874.1 (4) Å3	0.20 × 0.15 × 0.09 mm
Z = 4

Bruker SMART CCD diffractometer	2613 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
graphite	θmax = 25.0°, θmin = 2.1°
φ and ω scans	h = −11→11
14081 measured reflections	k = −22→22
3292 independent reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.3483P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3292 reflections	Δρmax = 0.15 e Å−3
253 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (2)

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	0.58636 (15)	0.10803 (8)	0.05439 (14)	0.0403 (4)
H1	0.5637	0.0581	0.0542	0.048*
C2	0.62867 (15)	0.12277 (7)	−0.07541 (15)	0.0403 (4)
C3	0.54762 (15)	0.10350 (8)	−0.20061 (15)	0.0421 (4)
C4	0.41722 (17)	0.06995 (9)	−0.23996 (16)	0.0520 (4)
H4	0.3633	0.0566	−0.1782	0.062*
C5	0.3700 (2)	0.05705 (10)	−0.37001 (18)	0.0652 (5)
H5	0.2839	0.0342	−0.3963	0.078*
C6	0.4482 (2)	0.07750 (11)	−0.46368 (19)	0.0690 (5)
H6	0.4132	0.0685	−0.5517	0.083*
C7	0.5762 (2)	0.11079 (10)	−0.42865 (17)	0.0627 (5)
H7	0.6286	0.1242	−0.4915	0.075*
C8	0.62532 (16)	0.12383 (8)	−0.29631 (16)	0.0467 (4)
C9	0.74842 (16)	0.15361 (8)	−0.10002 (17)	0.0477 (4)
H9	0.8208	0.1714	−0.0365	0.057*
C10	0.70384 (15)	0.11951 (8)	0.16965 (15)	0.0419 (4)
C11	0.82977 (15)	0.07764 (8)	0.20221 (15)	0.0425 (4)
C12	0.88333 (17)	0.02088 (9)	0.14286 (17)	0.0526 (4)
H12	0.8366	0.0042	0.0623	0.063*
C13	1.00687 (19)	−0.01001 (10)	0.2058 (2)	0.0657 (5)
H13	1.0432	−0.0481	0.1674	0.079*
C14	1.0784 (2)	0.01494 (11)	0.3263 (2)	0.0686 (5)
H14	1.1610	−0.0073	0.3671	0.082*
C15	1.02992 (19)	0.07111 (11)	0.38510 (18)	0.0624 (5)
H15	1.0783	0.0878	0.4650	0.075*
C16	0.90608 (16)	0.10251 (9)	0.32187 (15)	0.0496 (4)
C17	0.71121 (17)	0.16730 (9)	0.26731 (16)	0.0517 (4)
H17	0.6434	0.2015	0.2715	0.062*
C18	0.45208 (15)	0.14628 (8)	0.07105 (15)	0.0422 (4)
C19	0.42852 (19)	0.21445 (10)	0.0326 (2)	0.0742 (6)
H19	0.4949	0.2373	−0.0072	0.089*
C20	0.3091 (2)	0.24975 (10)	0.0516 (2)	0.0786 (7)
H20	0.2961	0.2962	0.0262	0.094*
C21	0.20928 (16)	0.21613 (9)	0.10831 (17)	0.0528 (4)
C22	0.23052 (18)	0.14779 (10)	0.14648 (19)	0.0647 (5)
H22	0.1631	0.1246	0.1846	0.078*
C23	0.35136 (17)	0.11352 (9)	0.12836 (17)	0.0569 (5)
H23	0.3653	0.0673	0.1554	0.068*
C24	0.08275 (18)	0.25223 (10)	0.12602 (18)	0.0602 (5)
N1	−0.01856 (16)	0.28075 (10)	0.13748 (17)	0.0757 (5)
N2	0.83216 (15)	0.15817 (8)	0.35857 (15)	0.0585 (4)
H2A	0.856 (2)	0.1831 (12)	0.434 (2)	0.088 (7)*
N3	0.74724 (15)	0.15470 (7)	−0.23225 (15)	0.0539 (4)
H3A	0.814 (2)	0.1722 (10)	−0.2680 (19)	0.069 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0363 (8)	0.0372 (8)	0.0485 (9)	0.0003 (6)	0.0109 (7)	0.0017 (7)
C2	0.0330 (7)	0.0403 (8)	0.0488 (9)	0.0030 (6)	0.0102 (7)	0.0026 (7)
C3	0.0387 (8)	0.0405 (8)	0.0478 (9)	0.0061 (7)	0.0101 (7)	0.0065 (7)
C4	0.0448 (9)	0.0555 (10)	0.0540 (10)	−0.0033 (8)	0.0051 (8)	0.0092 (8)
C5	0.0619 (11)	0.0678 (12)	0.0594 (12)	−0.0042 (9)	−0.0057 (9)	0.0031 (9)
C6	0.0797 (14)	0.0726 (13)	0.0498 (11)	0.0064 (11)	−0.0007 (10)	0.0013 (9)
C7	0.0752 (13)	0.0673 (12)	0.0496 (11)	0.0144 (10)	0.0219 (9)	0.0124 (9)
C8	0.0446 (9)	0.0450 (9)	0.0530 (10)	0.0077 (7)	0.0152 (7)	0.0085 (7)
C9	0.0383 (8)	0.0484 (9)	0.0574 (10)	−0.0027 (7)	0.0118 (7)	0.0019 (7)
C10	0.0369 (8)	0.0449 (9)	0.0455 (9)	−0.0026 (6)	0.0119 (7)	0.0005 (7)
C11	0.0366 (8)	0.0479 (9)	0.0443 (9)	−0.0022 (7)	0.0110 (7)	0.0054 (7)
C12	0.0470 (9)	0.0536 (10)	0.0576 (10)	0.0024 (8)	0.0109 (8)	0.0013 (8)
C13	0.0561 (11)	0.0599 (11)	0.0824 (14)	0.0144 (9)	0.0163 (10)	0.0089 (10)
C14	0.0497 (10)	0.0788 (14)	0.0744 (13)	0.0089 (10)	0.0035 (10)	0.0259 (11)
C15	0.0503 (10)	0.0829 (14)	0.0511 (10)	−0.0064 (10)	0.0017 (8)	0.0153 (10)
C16	0.0430 (9)	0.0604 (10)	0.0465 (9)	−0.0070 (8)	0.0110 (7)	0.0066 (8)
C17	0.0434 (9)	0.0565 (10)	0.0567 (10)	−0.0002 (8)	0.0131 (8)	−0.0054 (8)
C18	0.0351 (8)	0.0442 (9)	0.0483 (9)	−0.0013 (6)	0.0108 (7)	0.0011 (7)
C19	0.0574 (11)	0.0509 (11)	0.1275 (18)	0.0076 (9)	0.0519 (12)	0.0222 (11)
C20	0.0654 (12)	0.0509 (11)	0.1321 (19)	0.0138 (9)	0.0516 (13)	0.0227 (11)
C21	0.0400 (9)	0.0618 (11)	0.0593 (10)	0.0086 (8)	0.0163 (8)	0.0024 (8)
C22	0.0508 (10)	0.0704 (12)	0.0821 (13)	0.0072 (9)	0.0362 (9)	0.0218 (10)
C23	0.0503 (10)	0.0539 (10)	0.0723 (12)	0.0079 (8)	0.0264 (9)	0.0198 (9)
C24	0.0460 (10)	0.0738 (12)	0.0634 (12)	0.0099 (9)	0.0171 (8)	0.0044 (9)
N1	0.0533 (9)	0.0929 (13)	0.0860 (12)	0.0226 (9)	0.0265 (8)	0.0099 (9)
N2	0.0539 (9)	0.0728 (10)	0.0486 (9)	−0.0063 (8)	0.0088 (7)	−0.0127 (8)
N3	0.0445 (8)	0.0587 (9)	0.0643 (10)	−0.0013 (7)	0.0253 (7)	0.0109 (7)

C1—C10	1.502 (2)	C12—H12	0.9300
C1—C2	1.503 (2)	C13—C14	1.396 (3)
C1—C18	1.519 (2)	C13—H13	0.9300
C1—H1	0.9800	C14—C15	1.361 (3)
C2—C9	1.356 (2)	C14—H14	0.9300
C2—C3	1.435 (2)	C15—C16	1.384 (2)
C3—C4	1.399 (2)	C15—H15	0.9300
C3—C8	1.402 (2)	C16—N2	1.372 (2)
C4—C5	1.366 (2)	C17—N2	1.368 (2)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.389 (3)	C18—C19	1.372 (2)
C5—H5	0.9300	C18—C23	1.375 (2)
C6—C7	1.371 (3)	C19—C20	1.375 (2)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.391 (2)	C20—C21	1.373 (2)
C7—H7	0.9300	C20—H20	0.9300
C8—N3	1.369 (2)	C21—C22	1.372 (2)
C9—N3	1.371 (2)	C21—C24	1.437 (2)
C9—H9	0.9300	C22—C23	1.374 (2)
C10—C17	1.358 (2)	C22—H22	0.9300
C10—C11	1.437 (2)	C23—H23	0.9300
C11—C12	1.393 (2)	C24—N1	1.140 (2)
C11—C16	1.404 (2)	N2—H2A	0.91 (2)
C12—C13	1.377 (2)	N3—H3A	0.86 (2)
C10—C1—C2	113.60 (12)	C12—C13—H13	119.4
C10—C1—C18	111.50 (12)	C14—C13—H13	119.4
C2—C1—C18	112.65 (12)	C15—C14—C13	121.38 (17)
C10—C1—H1	106.1	C15—C14—H14	119.3
C2—C1—H1	106.1	C13—C14—H14	119.3
C18—C1—H1	106.1	C14—C15—C16	117.70 (17)
C9—C2—C3	106.14 (13)	C14—C15—H15	121.2
C9—C2—C1	128.86 (14)	C16—C15—H15	121.2
C3—C2—C1	124.97 (13)	N2—C16—C15	130.37 (17)
C4—C3—C8	118.91 (15)	N2—C16—C11	107.29 (14)
C4—C3—C2	133.59 (14)	C15—C16—C11	122.30 (17)
C8—C3—C2	107.49 (13)	C10—C17—N2	110.63 (15)
C5—C4—C3	119.26 (16)	C10—C17—H17	124.7
C5—C4—H4	120.4	N2—C17—H17	124.7
C3—C4—H4	120.4	C19—C18—C23	117.96 (14)
C4—C5—C6	121.14 (18)	C19—C18—C1	121.60 (13)
C4—C5—H5	119.4	C23—C18—C1	120.43 (14)
C6—C5—H5	119.4	C18—C19—C20	121.58 (16)
C7—C6—C5	121.16 (18)	C18—C19—H19	119.2
C7—C6—H6	119.4	C20—C19—H19	119.2
C5—C6—H6	119.4	C21—C20—C19	119.69 (17)
C6—C7—C8	118.03 (17)	C21—C20—H20	120.2
C6—C7—H7	121.0	C19—C20—H20	120.2
C8—C7—H7	121.0	C22—C21—C20	119.55 (15)
N3—C8—C7	131.44 (16)	C22—C21—C24	120.41 (16)
N3—C8—C3	107.05 (14)	C20—C21—C24	120.04 (16)
C7—C8—C3	121.50 (16)	C21—C22—C23	120.03 (15)
C2—C9—N3	110.08 (15)	C21—C22—H22	120.0
C2—C9—H9	125.0	C23—C22—H22	120.0
N3—C9—H9	125.0	C22—C23—C18	121.19 (16)
C17—C10—C11	105.91 (14)	C22—C23—H23	119.4
C17—C10—C1	128.49 (14)	C18—C23—H23	119.4
C11—C10—C1	125.50 (13)	N1—C24—C21	178.7 (2)
C12—C11—C16	118.77 (14)	C17—N2—C16	108.82 (14)
C12—C11—C10	133.90 (15)	C17—N2—H2A	125.3 (14)
C16—C11—C10	107.31 (14)	C16—N2—H2A	125.7 (14)
C13—C12—C11	118.70 (17)	C8—N3—C9	109.24 (13)
C13—C12—H12	120.7	C8—N3—H3A	126.3 (13)
C11—C12—H12	120.7	C9—N3—H3A	124.4 (13)
C12—C13—C14	121.11 (18)
C10—C1—C2—C9	−10.3 (2)	C11—C12—C13—C14	−0.5 (3)
C18—C1—C2—C9	117.73 (17)	C12—C13—C14—C15	−0.8 (3)
C10—C1—C2—C3	167.30 (13)	C13—C14—C15—C16	0.5 (3)
C18—C1—C2—C3	−64.69 (18)	C14—C15—C16—N2	178.63 (17)
C9—C2—C3—C4	179.30 (17)	C14—C15—C16—C11	1.1 (2)
C1—C2—C3—C4	1.3 (3)	C12—C11—C16—N2	179.62 (14)
C9—C2—C3—C8	0.43 (16)	C10—C11—C16—N2	−1.61 (17)
C1—C2—C3—C8	−177.61 (13)	C12—C11—C16—C15	−2.3 (2)
C8—C3—C4—C5	0.9 (2)	C10—C11—C16—C15	176.45 (14)
C2—C3—C4—C5	−177.91 (16)	C11—C10—C17—N2	−0.21 (18)
C3—C4—C5—C6	−0.9 (3)	C1—C10—C17—N2	176.26 (14)
C4—C5—C6—C7	0.6 (3)	C10—C1—C18—C19	87.1 (2)
C5—C6—C7—C8	−0.3 (3)	C2—C1—C18—C19	−42.0 (2)
C6—C7—C8—N3	179.15 (17)	C10—C1—C18—C23	−91.44 (18)
C6—C7—C8—C3	0.3 (3)	C2—C1—C18—C23	139.46 (16)
C4—C3—C8—N3	−179.68 (14)	C23—C18—C19—C20	0.7 (3)
C2—C3—C8—N3	−0.62 (17)	C1—C18—C19—C20	−177.84 (19)
C4—C3—C8—C7	−0.6 (2)	C18—C19—C20—C21	−1.1 (4)
C2—C3—C8—C7	178.47 (14)	C19—C20—C21—C22	0.6 (3)
C3—C2—C9—N3	−0.08 (17)	C19—C20—C21—C24	−178.70 (19)
C1—C2—C9—N3	177.86 (14)	C20—C21—C22—C23	0.2 (3)
C2—C1—C10—C17	115.39 (17)	C24—C21—C22—C23	179.56 (18)
C18—C1—C10—C17	−13.2 (2)	C21—C22—C23—C18	−0.6 (3)
C2—C1—C10—C11	−68.78 (18)	C19—C18—C23—C22	0.2 (3)
C18—C1—C10—C11	162.63 (13)	C1—C18—C23—C22	178.74 (16)
C17—C10—C11—C12	179.63 (17)	C10—C17—N2—C16	−0.81 (19)
C1—C10—C11—C12	3.0 (3)	C15—C16—N2—C17	−176.35 (17)
C17—C10—C11—C16	1.12 (17)	C11—C16—N2—C17	1.50 (18)
C1—C10—C11—C16	−175.49 (14)	C7—C8—N3—C9	−178.39 (17)
C16—C11—C12—C13	2.0 (2)	C3—C8—N3—C9	0.58 (17)
C10—C11—C12—C13	−176.41 (16)	C2—C9—N3—C8	−0.32 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1i	0.86 (2)	2.22 (2)	3.084 (2)	178.6 (18)
N2—H2A···N1ii	0.91 (2)	2.34 (2)	3.206 (2)	160.3 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N1i	0.86 (2)	2.22 (2)	3.084 (2)	178.6 (18)
N2—H2A⋯N1ii	0.91 (2)	2.34 (2)	3.206 (2)	160.3 (19)

Symmetry codes: (i) ; (ii) .