1-[6-(1H-Indol-1-yl)pyridin-2-yl]-1H-indole-3-carbaldehyde.

In the title compound, C22H15N3O, the dihedral angle between the two indole units is 33.72 (3)°. The mol-ecular structure features a weak intra-molecular C-H⋯N inter-action. In the crystal, weak C-H⋯O and C-H⋯π inter-actions, forming a two-dimensional network parallel to the bc plane.

Related literature

For the biological activity of indole derivatives, see: Macor et al. (1992 ▶); Andreani et al. (2001 ▶); Quetin-Leclercq (1994 ▶); Mukhopadhyay et al. (1981 ▶); Singh et al. (2000 ▶). For related structures see: Dileep et al. (2012 ▶); Wu et al. (2012 ▶)

Experimental

Crystal data

C22H15N3O

M = 337.37

Orthorhombic,

a = 18.2208 (7) Å

b = 15.7672 (9) Å

c = 11.7034 (7) Å

V = 3362.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.980, T max = 0.987

11189 measured reflections

3521 independent reflections

2072 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.118

S = 1.00

3521 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813034375/hg5369sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034375/hg5369Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813034375/hg5369Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H15N3O	F(000) = 1408
Mr = 337.37	Dx = 1.333 Mg m−3
Orthorhombic, Pnna	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2bc	Cell parameters from 3755 reflections
a = 18.2208 (7) Å	θ = 2.0–26.6°
b = 15.7672 (9) Å	µ = 0.08 mm−1
c = 11.7034 (7) Å	T = 295 K
V = 3362.3 (3) Å3	Block, colourless
Z = 8	0.25 × 0.20 × 0.15 mm

Bruker APEXII CCD diffractometer	3521 independent reflections
Radiation source: fine-focus sealed tube	2072 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 0 pixels mm-1	θmax = 26.7°, θmin = 2.1°
ω and φ scans	h = −14→22
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −19→13
Tmin = 0.980, Tmax = 0.987	l = −14→10
11189 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.3404P] where P = (Fo2 + 2Fc2)/3
3521 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.19452 (8)	0.09535 (11)	0.38032 (14)	0.0407 (4)
C2	0.23265 (9)	0.15297 (11)	0.44461 (16)	0.0493 (5)
H2	0.2599	0.1961	0.4109	0.059*
C3	0.22882 (10)	0.14407 (12)	0.56135 (16)	0.0541 (5)
H3	0.2545	0.1812	0.6083	0.065*
C4	0.18729 (10)	0.08067 (12)	0.60890 (15)	0.0506 (5)
H4	0.1840	0.0745	0.6877	0.061*
C5	0.15023 (8)	0.02580 (10)	0.53543 (14)	0.0408 (4)
C6	0.10521 (10)	−0.06632 (14)	0.69106 (16)	0.0595 (5)
H6	0.1322	−0.0413	0.7495	0.071*
C7	0.05930 (11)	−0.13186 (14)	0.70475 (18)	0.0658 (6)
H7	0.0495	−0.1599	0.7730	0.079*
C8	0.02821 (9)	−0.15088 (12)	0.59656 (16)	0.0510 (5)
C9	−0.02337 (10)	−0.21026 (13)	0.55946 (19)	0.0619 (6)
H9	−0.0439	−0.2484	0.6109	0.074*
C10	−0.04334 (10)	−0.21191 (13)	0.4474 (2)	0.0639 (6)
H10	−0.0771	−0.2520	0.4222	0.077*
C11	−0.01383 (10)	−0.15451 (13)	0.37027 (18)	0.0598 (5)
H11	−0.0286	−0.1565	0.2943	0.072*
C12	0.03711 (9)	−0.09435 (12)	0.40377 (16)	0.0500 (5)
H12	0.0564	−0.0557	0.3518	0.060*
C13	0.05850 (9)	−0.09360 (10)	0.51763 (15)	0.0417 (4)
C14	0.13419 (11)	0.07765 (11)	0.19300 (16)	0.0528 (5)
H14	0.0891	0.0604	0.2220	0.063*
C15	0.15005 (12)	0.08533 (11)	0.07958 (16)	0.0579 (5)
C16	0.22504 (11)	0.11196 (11)	0.07240 (16)	0.0530 (5)
C17	0.27264 (15)	0.12907 (13)	−0.01922 (19)	0.0745 (7)
H17	0.2566	0.1241	−0.0943	0.089*
C18	0.34277 (16)	0.15310 (15)	0.0044 (2)	0.0852 (8)
H18	0.3745	0.1651	−0.0557	0.102*
C19	0.36810 (13)	0.16008 (14)	0.1154 (2)	0.0807 (7)
H19	0.4164	0.1765	0.1283	0.097*
C20	0.32270 (11)	0.14309 (12)	0.20799 (19)	0.0610 (5)
H20	0.3396	0.1470	0.2828	0.073*
C21	0.25168 (10)	0.12027 (10)	0.18389 (15)	0.0489 (5)
C22	0.09838 (16)	0.06891 (14)	−0.0091 (2)	0.0804 (7)
H22	0.0518	0.0513	0.0129	0.096*
N1	0.15424 (7)	0.03227 (8)	0.42256 (11)	0.0408 (4)
N2	0.10689 (7)	−0.04099 (9)	0.57769 (11)	0.0438 (4)
N3	0.19390 (8)	0.09876 (9)	0.25834 (12)	0.0464 (4)
O1	0.10984 (12)	0.07594 (11)	−0.11088 (14)	0.1121 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0422 (9)	0.0379 (10)	0.0420 (10)	0.0049 (8)	0.0027 (8)	0.0014 (8)
C2	0.0513 (11)	0.0412 (10)	0.0555 (12)	−0.0061 (9)	0.0021 (9)	−0.0001 (9)
C3	0.0583 (12)	0.0485 (11)	0.0555 (12)	−0.0063 (10)	−0.0070 (9)	−0.0080 (10)
C4	0.0599 (11)	0.0518 (12)	0.0402 (11)	−0.0027 (10)	−0.0033 (9)	−0.0020 (9)
C5	0.0404 (9)	0.0405 (10)	0.0415 (10)	0.0049 (8)	0.0026 (8)	0.0004 (8)
C6	0.0656 (12)	0.0715 (14)	0.0415 (11)	−0.0075 (11)	0.0011 (9)	0.0080 (10)
C7	0.0693 (13)	0.0733 (15)	0.0548 (13)	−0.0130 (12)	0.0074 (10)	0.0201 (11)
C8	0.0455 (10)	0.0474 (11)	0.0600 (12)	0.0034 (9)	0.0045 (9)	0.0108 (10)
C9	0.0523 (12)	0.0494 (13)	0.0841 (16)	−0.0028 (10)	0.0022 (11)	0.0159 (11)
C10	0.0525 (12)	0.0461 (13)	0.0930 (18)	−0.0048 (10)	−0.0075 (12)	0.0009 (12)
C11	0.0575 (12)	0.0569 (13)	0.0650 (13)	−0.0005 (11)	−0.0078 (10)	−0.0025 (11)
C12	0.0501 (10)	0.0461 (11)	0.0537 (12)	−0.0003 (9)	0.0010 (9)	0.0014 (9)
C13	0.0378 (9)	0.0380 (10)	0.0493 (11)	0.0060 (8)	0.0033 (8)	0.0006 (9)
C14	0.0634 (12)	0.0436 (11)	0.0515 (12)	−0.0067 (10)	−0.0049 (10)	0.0035 (9)
C15	0.0851 (15)	0.0409 (11)	0.0476 (12)	−0.0030 (11)	−0.0051 (11)	0.0012 (9)
C16	0.0813 (14)	0.0307 (10)	0.0469 (12)	0.0023 (10)	0.0109 (10)	0.0005 (9)
C17	0.117 (2)	0.0508 (13)	0.0559 (14)	0.0038 (14)	0.0237 (14)	−0.0006 (10)
C18	0.100 (2)	0.0672 (16)	0.088 (2)	−0.0025 (15)	0.0469 (16)	0.0001 (14)
C19	0.0740 (15)	0.0641 (15)	0.104 (2)	−0.0029 (12)	0.0309 (15)	−0.0014 (14)
C20	0.0591 (12)	0.0508 (12)	0.0729 (14)	0.0022 (10)	0.0118 (11)	0.0007 (10)
C21	0.0614 (12)	0.0323 (10)	0.0530 (12)	−0.0003 (9)	0.0097 (10)	0.0017 (9)
C22	0.125 (2)	0.0581 (14)	0.0584 (15)	−0.0025 (14)	−0.0222 (14)	−0.0043 (12)
N1	0.0427 (8)	0.0375 (8)	0.0422 (9)	0.0005 (7)	0.0031 (6)	0.0023 (7)
N2	0.0475 (8)	0.0438 (9)	0.0400 (9)	−0.0009 (7)	0.0039 (7)	0.0025 (7)
N3	0.0538 (9)	0.0405 (9)	0.0448 (9)	−0.0051 (7)	0.0049 (7)	0.0043 (7)
O1	0.189 (2)	0.0900 (13)	0.0577 (12)	0.0140 (13)	−0.0299 (12)	−0.0115 (9)

C1—N1	1.331 (2)	C11—H11	0.9300
C1—C2	1.369 (2)	C12—C13	1.388 (2)
C1—N3	1.429 (2)	C12—H12	0.9300
C2—C3	1.375 (2)	C13—N2	1.400 (2)
C2—H2	0.9300	C14—C15	1.364 (2)
C3—C4	1.372 (2)	C14—N3	1.371 (2)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.394 (2)	C15—C22	1.425 (3)
C4—H4	0.9300	C15—C16	1.432 (3)
C5—N1	1.3269 (19)	C16—C21	1.398 (2)
C5—N2	1.406 (2)	C16—C17	1.405 (3)
C6—C7	1.339 (3)	C17—C18	1.361 (3)
C6—N2	1.386 (2)	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.383 (3)
C7—C8	1.419 (3)	C18—H18	0.9300
C7—H7	0.9300	C19—C20	1.390 (3)
C8—C9	1.396 (3)	C19—H19	0.9300
C8—C13	1.405 (2)	C20—C21	1.372 (3)
C9—C10	1.362 (3)	C20—H20	0.9300
C9—H9	0.9300	C21—N3	1.408 (2)
C10—C11	1.386 (3)	C22—O1	1.215 (3)
C10—H10	0.9300	C22—H22	0.9300
C11—C12	1.384 (3)
N1—C1—C2	124.85 (16)	C12—C13—C8	121.02 (17)
N1—C1—N3	113.26 (15)	N2—C13—C8	107.35 (16)
C2—C1—N3	121.88 (16)	C15—C14—N3	110.69 (17)
C1—C2—C3	116.90 (17)	C15—C14—H14	124.7
C1—C2—H2	121.5	N3—C14—H14	124.7
C3—C2—H2	121.5	C14—C15—C22	123.6 (2)
C4—C3—C2	120.36 (17)	C14—C15—C16	106.58 (17)
C4—C3—H3	119.8	C22—C15—C16	129.9 (2)
C2—C3—H3	119.8	C21—C16—C17	118.7 (2)
C3—C4—C5	117.99 (17)	C21—C16—C15	107.70 (16)
C3—C4—H4	121.0	C17—C16—C15	133.6 (2)
C5—C4—H4	121.0	C18—C17—C16	118.6 (2)
N1—C5—C4	122.65 (16)	C18—C17—H17	120.7
N1—C5—N2	116.02 (15)	C16—C17—H17	120.7
C4—C5—N2	121.32 (16)	C17—C18—C19	121.7 (2)
C7—C6—N2	110.53 (17)	C17—C18—H18	119.1
C7—C6—H6	124.7	C19—C18—H18	119.1
N2—C6—H6	124.7	C18—C19—C20	121.2 (2)
C6—C7—C8	107.79 (17)	C18—C19—H19	119.4
C6—C7—H7	126.1	C20—C19—H19	119.4
C8—C7—H7	126.1	C21—C20—C19	116.9 (2)
C9—C8—C13	119.42 (18)	C21—C20—H20	121.6
C9—C8—C7	133.48 (18)	C19—C20—H20	121.6
C13—C8—C7	107.10 (17)	C20—C21—C16	122.93 (17)
C10—C9—C8	119.50 (19)	C20—C21—N3	129.86 (18)
C10—C9—H9	120.2	C16—C21—N3	107.17 (16)
C8—C9—H9	120.2	O1—C22—C15	125.7 (3)
C9—C10—C11	120.73 (19)	O1—C22—H22	117.1
C9—C10—H10	119.6	C15—C22—H22	117.1
C11—C10—H10	119.6	C5—N1—C1	117.23 (14)
C12—C11—C10	121.54 (19)	C6—N2—C13	107.22 (14)
C12—C11—H11	119.2	C6—N2—C5	124.40 (15)
C10—C11—H11	119.2	C13—N2—C5	128.38 (14)
C11—C12—C13	117.77 (17)	C14—N3—C21	107.86 (15)
C11—C12—H12	121.1	C14—N3—C1	123.68 (14)
C13—C12—H12	121.1	C21—N3—C1	128.43 (15)
C12—C13—N2	131.59 (16)
N1—C1—C2—C3	0.3 (3)	C19—C20—C21—N3	179.32 (18)
N3—C1—C2—C3	179.43 (15)	C17—C16—C21—C20	−1.1 (3)
C1—C2—C3—C4	−1.1 (3)	C15—C16—C21—C20	178.44 (17)
C2—C3—C4—C5	0.6 (3)	C17—C16—C21—N3	−179.34 (16)
C3—C4—C5—N1	0.6 (2)	C15—C16—C21—N3	0.19 (19)
C3—C4—C5—N2	179.67 (16)	C14—C15—C22—O1	179.0 (2)
N2—C6—C7—C8	−0.6 (2)	C16—C15—C22—O1	−0.8 (4)
C6—C7—C8—C9	−178.4 (2)	C4—C5—N1—C1	−1.4 (2)
C6—C7—C8—C13	0.5 (2)	N2—C5—N1—C1	179.54 (13)
C13—C8—C9—C10	0.2 (3)	C2—C1—N1—C5	0.9 (2)
C7—C8—C9—C10	178.9 (2)	N3—C1—N1—C5	−178.30 (13)
C8—C9—C10—C11	−1.0 (3)	C7—C6—N2—C13	0.6 (2)
C9—C10—C11—C12	0.6 (3)	C7—C6—N2—C5	−179.48 (16)
C10—C11—C12—C13	0.6 (3)	C12—C13—N2—C6	177.36 (18)
C11—C12—C13—N2	−178.68 (16)	C8—C13—N2—C6	−0.26 (18)
C11—C12—C13—C8	−1.3 (3)	C12—C13—N2—C5	−2.6 (3)
C9—C8—C13—C12	1.0 (3)	C8—C13—N2—C5	179.79 (15)
C7—C8—C13—C12	−178.03 (16)	N1—C5—N2—C6	169.29 (16)
C9—C8—C13—N2	178.90 (15)	C4—C5—N2—C6	−9.8 (2)
C7—C8—C13—N2	−0.11 (19)	N1—C5—N2—C13	−10.8 (2)
N3—C14—C15—C22	−179.03 (18)	C4—C5—N2—C13	170.11 (16)
N3—C14—C15—C16	0.8 (2)	C15—C14—N3—C21	−0.7 (2)
C14—C15—C16—C21	−0.6 (2)	C15—C14—N3—C1	−178.77 (16)
C22—C15—C16—C21	179.2 (2)	C20—C21—N3—C14	−177.78 (18)
C14—C15—C16—C17	178.8 (2)	C16—C21—N3—C14	0.30 (19)
C22—C15—C16—C17	−1.4 (4)	C20—C21—N3—C1	0.2 (3)
C21—C16—C17—C18	0.0 (3)	C16—C21—N3—C1	178.24 (16)
C15—C16—C17—C18	−179.4 (2)	N1—C1—N3—C14	34.4 (2)
C16—C17—C18—C19	0.7 (3)	C2—C1—N3—C14	−144.83 (17)
C17—C18—C19—C20	−0.3 (4)	N1—C1—N3—C21	−143.23 (16)
C18—C19—C20—C21	−0.8 (3)	C2—C1—N3—C21	37.5 (3)
C19—C20—C21—C16	1.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.50	3.227 (3)	135
C12—H12···N1	0.93	2.41	2.931 (2)	116
C2—H2···Cg5ii	0.93	2.73	3.554 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg5 is the centroid of the C16–C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.50	3.227 (3)	135
C12—H12⋯N1	0.93	2.41	2.931 (2)	116
C2—H2⋯Cg5ii	0.93	2.73	3.554 (2)	148

Symmetry codes: (i) ; (ii) .