2,2-Bis(1H-indol-3-yl)indolin-3-one.

In the title mol-ecule, C(24)H(17)N(3)O, the mean plane of the indolone ring forms dihedral angles of 112.0 (1) and 103.1 (1)° with the planes of the two indole rings. The dihedral angle between the mean planes of the two indole rings is 63.5 (1)°. In the crystal structure, mol-ecules are linked via inter-molecular N-H⋯O hydrogen bonds, forming a two-dimensional network parallel to the ab plane.

Related literature

For the applications of indole derivatives, see: Ramesh et al. (2009 ▶). For the isolation of the title compound as a natural product, see: Ganachaud et al. (2008 ▶); Stull et al. (1995 ▶).

Experimental

Crystal data

C24H17N3O

M = 363.41

Monoclinic,

a = 10.559 (4) Å

b = 8.931 (3) Å

c = 19.899 (7) Å

β = 98.480 (6)°

V = 1856.1 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.40 × 0.35 × 0.15 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.968, T max = 0.988

14004 measured reflections

4245 independent reflections

3606 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.118

S = 1.06

4245 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017553/lh2811sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017553/lh2811Isup2.hkl

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

C24H17N3O	F(000) = 760
Mr = 363.41	Dx = 1.300 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4234 reflections
a = 10.559 (4) Å	θ = 3.0–27.5°
b = 8.931 (3) Å	µ = 0.08 mm−1
c = 19.899 (7) Å	T = 293 K
β = 98.480 (6)°	Prism, yellow
V = 1856.1 (11) Å3	0.40 × 0.35 × 0.15 mm
Z = 4

Rigaku Mercury CCD diffractometer	4245 independent reflections
Radiation source: fine-focus sealed tube	3606 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 14.6306 pixels mm-1	θmax = 27.5°, θmin = 2.1°
CCD_Profile_fitting scans	h = −11→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −11→11
Tmin = 0.968, Tmax = 0.988	l = −22→25
14004 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0513P)2 + 0.4603P] where P = (Fo2 + 2Fc2)/3
4245 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.19 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
O1	0.96565 (9)	0.43252 (10)	0.15911 (5)	0.0369 (2)
N1	0.95403 (12)	0.04726 (13)	0.11858 (6)	0.0406 (3)
H1A	0.9668	−0.0474	0.1239	0.049*
N2	0.75509 (12)	0.05077 (15)	0.28328 (7)	0.0490 (3)
H2B	0.6914	−0.0017	0.2923	0.059*
N3	1.31856 (12)	0.10180 (15)	0.26178 (6)	0.0471 (3)
H3B	1.3724	0.0659	0.2945	0.056*
C1	0.89773 (13)	0.11138 (16)	0.05986 (7)	0.0374 (3)
C2	0.85094 (14)	0.0420 (2)	−0.00189 (8)	0.0483 (4)
H2A	0.8532	−0.0615	−0.0065	0.058*
C3	0.80181 (17)	0.1314 (2)	−0.05518 (8)	0.0635 (5)
H3A	0.7706	0.0868	−0.0966	0.076*
C4	0.7967 (2)	0.2867 (3)	−0.04991 (9)	0.0746 (6)
H4A	0.7630	0.3437	−0.0874	0.090*
C5	0.84151 (19)	0.3558 (2)	0.01064 (8)	0.0604 (5)
H5A	0.8383	0.4595	0.0147	0.072*
C6	0.89185 (13)	0.26719 (17)	0.06585 (7)	0.0392 (3)
C7	0.94976 (12)	0.30732 (14)	0.13383 (6)	0.0315 (3)
C8	0.99057 (13)	0.15946 (14)	0.17220 (6)	0.0321 (3)
C9	0.81798 (14)	0.15783 (17)	0.32497 (7)	0.0417 (3)
C10	0.79721 (18)	0.2065 (2)	0.38885 (8)	0.0557 (4)
H10A	0.7324	0.1655	0.4100	0.067*
C11	0.8753 (2)	0.3166 (2)	0.41938 (8)	0.0616 (5)
H11A	0.8635	0.3509	0.4621	0.074*
C12	0.97253 (17)	0.3786 (2)	0.38756 (8)	0.0550 (4)
H12A	1.0236	0.4541	0.4093	0.066*
C13	0.99417 (15)	0.32982 (17)	0.32449 (7)	0.0424 (3)
H13A	1.0597	0.3712	0.3040	0.051*
C14	0.91605 (13)	0.21709 (15)	0.29179 (7)	0.0351 (3)
C15	0.90865 (13)	0.13904 (15)	0.22798 (7)	0.0342 (3)
C16	0.80919 (14)	0.04053 (17)	0.22537 (8)	0.0432 (3)
H16A	0.7823	−0.0240	0.1894	0.052*
C17	1.34968 (13)	0.18478 (15)	0.20847 (7)	0.0380 (3)
C18	1.46884 (15)	0.23042 (18)	0.19416 (9)	0.0491 (4)
H18A	1.5436	0.2065	0.2230	0.059*
C19	1.47219 (15)	0.31203 (18)	0.13592 (9)	0.0511 (4)
H19A	1.5507	0.3436	0.1251	0.061*
C20	1.36003 (15)	0.34840 (18)	0.09265 (8)	0.0461 (4)
H20A	1.3651	0.4030	0.0533	0.055*
C21	1.24194 (14)	0.30469 (15)	0.10722 (7)	0.0380 (3)
H21A	1.1679	0.3304	0.0782	0.046*
C22	1.23417 (12)	0.22113 (14)	0.16619 (6)	0.0322 (3)
C23	1.13200 (12)	0.15690 (14)	0.19763 (6)	0.0326 (3)
C24	1.18882 (14)	0.08515 (16)	0.25473 (7)	0.0412 (3)
H24A	1.1454	0.0325	0.2846	0.049*

	U11	U22	U33	U12	U13	U23
O1	0.0351 (5)	0.0344 (5)	0.0407 (5)	0.0007 (4)	0.0040 (4)	−0.0052 (4)
N1	0.0497 (7)	0.0320 (6)	0.0391 (6)	−0.0014 (5)	0.0029 (5)	−0.0058 (5)
N2	0.0361 (7)	0.0527 (8)	0.0603 (8)	−0.0086 (6)	0.0138 (6)	0.0105 (6)
N3	0.0361 (7)	0.0560 (8)	0.0472 (7)	0.0108 (6)	−0.0002 (5)	0.0156 (6)
C1	0.0288 (7)	0.0464 (8)	0.0367 (7)	−0.0010 (6)	0.0041 (5)	−0.0075 (6)
C2	0.0377 (8)	0.0583 (9)	0.0474 (8)	−0.0003 (7)	0.0016 (6)	−0.0203 (7)
C3	0.0549 (11)	0.0890 (14)	0.0415 (9)	0.0140 (10)	−0.0100 (8)	−0.0235 (9)
C4	0.0916 (16)	0.0844 (14)	0.0395 (9)	0.0287 (12)	−0.0181 (9)	−0.0053 (9)
C5	0.0750 (12)	0.0580 (10)	0.0423 (8)	0.0195 (9)	−0.0110 (8)	−0.0010 (7)
C6	0.0353 (7)	0.0455 (8)	0.0347 (7)	0.0055 (6)	−0.0015 (6)	−0.0053 (6)
C7	0.0252 (6)	0.0364 (7)	0.0330 (6)	0.0018 (5)	0.0048 (5)	−0.0025 (5)
C8	0.0327 (7)	0.0322 (6)	0.0311 (6)	−0.0015 (5)	0.0034 (5)	−0.0032 (5)
C9	0.0367 (8)	0.0463 (8)	0.0437 (8)	0.0066 (6)	0.0114 (6)	0.0125 (6)
C10	0.0577 (10)	0.0660 (11)	0.0486 (9)	0.0120 (9)	0.0249 (8)	0.0170 (8)
C11	0.0735 (13)	0.0775 (13)	0.0365 (8)	0.0178 (10)	0.0174 (8)	0.0021 (8)
C12	0.0601 (11)	0.0623 (10)	0.0419 (8)	0.0047 (8)	0.0051 (7)	−0.0090 (7)
C13	0.0425 (8)	0.0485 (8)	0.0366 (7)	−0.0009 (6)	0.0067 (6)	−0.0014 (6)
C14	0.0327 (7)	0.0391 (7)	0.0338 (6)	0.0038 (5)	0.0058 (5)	0.0054 (5)
C15	0.0309 (7)	0.0353 (7)	0.0359 (7)	−0.0004 (5)	0.0039 (5)	0.0026 (5)
C16	0.0367 (8)	0.0436 (8)	0.0486 (8)	−0.0051 (6)	0.0044 (6)	0.0023 (6)
C17	0.0338 (7)	0.0366 (7)	0.0430 (7)	0.0063 (5)	0.0037 (6)	0.0013 (6)
C18	0.0297 (7)	0.0524 (9)	0.0640 (10)	0.0058 (6)	0.0030 (7)	0.0001 (8)
C19	0.0359 (8)	0.0515 (9)	0.0686 (11)	−0.0027 (7)	0.0172 (7)	−0.0014 (8)
C20	0.0472 (9)	0.0473 (8)	0.0463 (8)	−0.0034 (7)	0.0154 (7)	0.0031 (7)
C21	0.0371 (7)	0.0407 (7)	0.0359 (7)	0.0006 (6)	0.0049 (6)	0.0006 (6)
C22	0.0313 (7)	0.0308 (6)	0.0346 (6)	0.0036 (5)	0.0051 (5)	−0.0022 (5)
C23	0.0319 (7)	0.0327 (6)	0.0334 (6)	0.0029 (5)	0.0056 (5)	0.0001 (5)
C24	0.0376 (8)	0.0436 (8)	0.0428 (8)	0.0054 (6)	0.0070 (6)	0.0096 (6)

O1—C7	1.2274 (16)	C9—C14	1.411 (2)
N1—C1	1.3571 (18)	C10—C11	1.367 (3)
N1—C8	1.4731 (16)	C10—H10A	0.9300
N1—H1A	0.8600	C11—C12	1.398 (3)
N2—C16	1.363 (2)	C11—H11A	0.9300
N2—C9	1.371 (2)	C12—C13	1.379 (2)
N2—H2B	0.8600	C12—H12A	0.9300
N3—C24	1.3645 (19)	C13—C14	1.400 (2)
N3—C17	1.3731 (19)	C13—H13A	0.9300
N3—H3B	0.8600	C14—C15	1.4405 (19)
C1—C6	1.399 (2)	C15—C16	1.3652 (19)
C1—C2	1.3997 (19)	C16—H16A	0.9300
C2—C3	1.367 (3)	C17—C18	1.391 (2)
C2—H2A	0.9300	C17—C22	1.4136 (19)
C3—C4	1.392 (3)	C18—C19	1.374 (2)
C3—H3A	0.9300	C18—H18A	0.9300
C4—C5	1.374 (2)	C19—C20	1.396 (2)
C4—H4A	0.9300	C19—H19A	0.9300
C5—C6	1.394 (2)	C20—C21	1.378 (2)
C5—H5A	0.9300	C20—H20A	0.9300
C6—C7	1.4451 (18)	C21—C22	1.4031 (19)
C7—C8	1.5542 (18)	C21—H21A	0.9300
C8—C23	1.5046 (19)	C22—C23	1.4434 (18)
C8—C15	1.5155 (19)	C23—C24	1.3640 (19)
C9—C10	1.391 (2)	C24—H24A	0.9300
C1—N1—C8	111.79 (11)	C10—C11—C12	121.26 (16)
C1—N1—H1A	124.1	C10—C11—H11A	119.4
C8—N1—H1A	124.1	C12—C11—H11A	119.4
C16—N2—C9	109.42 (12)	C13—C12—C11	121.24 (17)
C16—N2—H2B	125.3	C13—C12—H12A	119.4
C9—N2—H2B	125.3	C11—C12—H12A	119.4
C24—N3—C17	109.29 (12)	C12—C13—C14	119.00 (15)
C24—N3—H3B	125.4	C12—C13—H13A	120.5
C17—N3—H3B	125.4	C14—C13—H13A	120.5
N1—C1—C6	111.45 (12)	C13—C14—C9	118.37 (13)
N1—C1—C2	128.48 (14)	C13—C14—C15	135.19 (13)
C6—C1—C2	120.06 (14)	C9—C14—C15	106.43 (13)
C3—C2—C1	117.83 (16)	C16—C15—C14	106.67 (12)
C3—C2—H2A	121.1	C16—C15—C8	124.66 (13)
C1—C2—H2A	121.1	C14—C15—C8	128.66 (12)
C2—C3—C4	122.53 (15)	N2—C16—C15	109.91 (14)
C2—C3—H3A	118.7	N2—C16—H16A	125.0
C4—C3—H3A	118.7	C15—C16—H16A	125.0
C5—C4—C3	120.11 (17)	N3—C17—C18	130.01 (13)
C5—C4—H4A	119.9	N3—C17—C22	107.46 (12)
C3—C4—H4A	119.9	C18—C17—C22	122.53 (14)
C4—C5—C6	118.52 (17)	C19—C18—C17	117.69 (14)
C4—C5—H5A	120.7	C19—C18—H18A	121.2
C6—C5—H5A	120.7	C17—C18—H18A	121.2
C5—C6—C1	120.95 (14)	C18—C19—C20	121.24 (14)
C5—C6—C7	131.01 (14)	C18—C19—H19A	119.4
C1—C6—C7	107.97 (12)	C20—C19—H19A	119.4
O1—C7—C6	128.53 (13)	C21—C20—C19	121.07 (14)
O1—C7—C8	124.16 (12)	C21—C20—H20A	119.5
C6—C7—C8	107.31 (11)	C19—C20—H20A	119.5
N1—C8—C23	111.98 (11)	C20—C21—C22	119.54 (13)
N1—C8—C15	109.37 (11)	C20—C21—H21A	120.2
C23—C8—C15	113.41 (11)	C22—C21—H21A	120.2
N1—C8—C7	101.43 (10)	C21—C22—C17	117.92 (12)
C23—C8—C7	111.57 (10)	C21—C22—C23	135.52 (12)
C15—C8—C7	108.37 (11)	C17—C22—C23	106.56 (12)
N2—C9—C10	130.02 (15)	C24—C23—C22	106.43 (12)
N2—C9—C14	107.57 (13)	C24—C23—C8	125.45 (12)
C10—C9—C14	122.41 (15)	C22—C23—C8	128.05 (11)
C11—C10—C9	117.71 (15)	C23—C24—N3	110.25 (13)
C11—C10—H10A	121.1	C23—C24—H24A	124.9
C9—C10—H10A	121.1	N3—C24—H24A	124.9

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1i	0.86	2.12	2.9412 (17)	159
N3—H3B···O1ii	0.86	2.18	2.9830 (16)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O1i	0.86	2.12	2.9412 (17)	159
N3—H3B⋯O1ii	0.86	2.18	2.9830 (16)	156

Symmetry codes: (i) ; (ii) .