2-(1H-indol-3-ylcarbon-yl)acetonitrile.

The title compound, C(11)H(8)N(2)O, crystallizes with two crystallographically independent mol-ecules in the asymmetric unit which are approximately perpendicular to each other [79.97 (6)°]. The indole ring system is planar [r.m.s. deviation = 0.010 (1) Å]. The crystal structure is stabilized by inter-molecular C-H⋯N and N-H⋯O inter-actions.

Related literature

For the use of indole derivatives as bioactive drugs, see: Stevenson et al. (2000 ▶). For their biological properties, see: Harris & Uhle (1960 ▶); Ho et al. (1986 ▶). For their high aldose reductase inhibitory activity, see: Rajeswaran et al. (1999 ▶). For a related structure, see: Ramesh et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H8N2O

M = 184.19

Triclinic,

a = 7.3439 (2) Å

b = 7.3534 (2) Å

c = 18.2475 (5) Å

α = 83.402 (2)°

β = 78.890 (2)°

γ = 73.501 (1)°

V = 925.23 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.974, T max = 0.983

18838 measured reflections

3253 independent reflections

2717 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.100

S = 1.06

3253 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001342/bt2839sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001342/bt2839Isup2.hkl

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

C11H8N2O	Z = 4
Mr = 184.19	F(000) = 384
Triclinic, P1	Dx = 1.322 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3439 (2) Å	Cell parameters from 3554 reflections
b = 7.3534 (2) Å	θ = 1.1–25.0°
c = 18.2475 (5) Å	µ = 0.09 mm−1
α = 83.402 (2)°	T = 293 K
β = 78.890 (2)°	Block, colourless
γ = 73.501 (1)°	0.30 × 0.30 × 0.20 mm
V = 925.23 (4) Å3

Bruker Kappa APEXII area-detector diffractometer	3253 independent reflections
Radiation source: fine-focus sealed tube	2717 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω and φ scans	θmax = 25.0°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −7→8
Tmin = 0.974, Tmax = 0.983	k = −8→8
18838 measured reflections	l = −21→21

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0404P)2 + 0.2437P] where P = (Fo2 + 2Fc2)/3
3253 reflections	(Δ/σ)max = 0.008
253 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.16 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	0.13478 (16)	0.2464 (2)	1.01403 (7)	0.0659 (4)
O1'	0.76317 (17)	0.33368 (14)	0.47980 (6)	0.0543 (3)
N1	0.7573 (2)	0.2397 (2)	1.00692 (9)	0.0619 (4)
H1	0.8678	0.2314	1.0183	0.074*
N1'	0.77718 (19)	−0.28849 (17)	0.48288 (7)	0.0479 (3)
H1'	0.7932	−0.4024	0.4709	0.057*
C2	0.6023 (2)	0.2202 (2)	1.05570 (11)	0.0567 (4)
H2	0.5977	0.1956	1.1071	0.068*
C2'	0.8188 (2)	−0.1468 (2)	0.43593 (9)	0.0441 (4)
H2'	0.8689	−0.1567	0.3853	0.053*
C3	0.4501 (2)	0.2418 (2)	1.01850 (9)	0.0475 (4)
C3'	0.7768 (2)	0.01550 (19)	0.47349 (8)	0.0385 (3)
C4	0.5195 (2)	0.2786 (2)	0.94094 (9)	0.0478 (4)
C4'	0.7012 (2)	−0.03211 (19)	0.54959 (8)	0.0389 (3)
C5'	0.6267 (2)	0.0675 (2)	0.61400 (9)	0.0479 (4)
H5'	0.6214	0.1956	0.6133	0.058*
C5	0.4391 (2)	0.3141 (2)	0.87583 (10)	0.0565 (4)
H5	0.3107	0.3175	0.8777	0.068*
C6'	0.5613 (3)	−0.0269 (2)	0.67853 (9)	0.0569 (4)
H6'	0.5098	0.0389	0.7216	0.068*
C6	0.5521 (3)	0.3437 (3)	0.80899 (11)	0.0678 (5)
H6	0.4991	0.3687	0.7653	0.081*
C7'	0.5702 (3)	−0.2187 (2)	0.68090 (10)	0.0583 (4)
H7'	0.5269	−0.2792	0.7257	0.070*
C7	0.7456 (3)	0.3370 (3)	0.80531 (13)	0.0742 (6)
H7	0.8195	0.3559	0.7591	0.089*
C8'	0.6417 (2)	−0.3200 (2)	0.61849 (10)	0.0527 (4)
H8'	0.6475	−0.4483	0.6199	0.063*
C8	0.8287 (3)	0.3032 (3)	0.86844 (13)	0.0684 (5)
H8	0.9574	0.2993	0.8660	0.082*
C9	0.7140 (2)	0.2751 (2)	0.93550 (11)	0.0540 (4)
C9'	0.7049 (2)	−0.2241 (2)	0.55332 (8)	0.0419 (3)
C10	0.2612 (2)	0.2273 (2)	1.05110 (9)	0.0482 (4)
C10'	0.8024 (2)	0.19645 (19)	0.44251 (8)	0.0396 (3)
C11'	0.8851 (2)	0.2118 (2)	0.35992 (8)	0.0455 (4)
H11A	1.0210	0.1451	0.3524	0.055*
H11B	0.8214	0.1505	0.3322	0.055*
C11	0.2210 (2)	0.1842 (3)	1.13506 (9)	0.0562 (4)
H11C	0.3072	0.0628	1.1480	0.067*
H11D	0.2474	0.2809	1.1602	0.067*
C12	0.0245 (3)	0.1779 (3)	1.16141 (9)	0.0605 (5)
C12'	0.8620 (2)	0.4067 (2)	0.33086 (9)	0.0513 (4)
N13	−0.1297 (3)	0.1725 (3)	1.18193 (9)	0.0878 (6)
N13'	0.8429 (3)	0.5597 (2)	0.30820 (9)	0.0806 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0436 (6)	0.1027 (10)	0.0585 (7)	−0.0291 (6)	−0.0166 (6)	0.0039 (7)
O1'	0.0829 (8)	0.0340 (6)	0.0491 (6)	−0.0248 (5)	−0.0035 (6)	−0.0054 (5)
N1	0.0409 (8)	0.0647 (9)	0.0868 (11)	−0.0155 (7)	−0.0217 (8)	−0.0100 (8)
N1'	0.0611 (8)	0.0298 (6)	0.0566 (8)	−0.0163 (6)	−0.0112 (6)	−0.0059 (6)
C2	0.0469 (9)	0.0597 (10)	0.0689 (11)	−0.0150 (8)	−0.0187 (8)	−0.0087 (8)
C2'	0.0521 (9)	0.0379 (8)	0.0453 (8)	−0.0158 (6)	−0.0082 (7)	−0.0056 (6)
C3	0.0412 (8)	0.0451 (9)	0.0602 (10)	−0.0126 (7)	−0.0144 (7)	−0.0072 (7)
C3'	0.0432 (8)	0.0323 (7)	0.0435 (8)	−0.0136 (6)	−0.0109 (6)	−0.0027 (6)
C4	0.0420 (8)	0.0367 (8)	0.0674 (11)	−0.0124 (6)	−0.0128 (7)	−0.0038 (7)
C4'	0.0409 (8)	0.0333 (7)	0.0461 (8)	−0.0130 (6)	−0.0123 (6)	−0.0011 (6)
C5'	0.0566 (9)	0.0388 (8)	0.0501 (9)	−0.0144 (7)	−0.0095 (7)	−0.0043 (7)
C5	0.0509 (9)	0.0527 (10)	0.0689 (11)	−0.0184 (8)	−0.0160 (8)	0.0048 (8)
C6'	0.0671 (11)	0.0573 (10)	0.0458 (9)	−0.0172 (8)	−0.0067 (8)	−0.0043 (8)
C6	0.0761 (13)	0.0590 (11)	0.0706 (13)	−0.0260 (9)	−0.0147 (10)	0.0103 (9)
C7'	0.0656 (11)	0.0587 (11)	0.0514 (10)	−0.0237 (8)	−0.0092 (8)	0.0103 (8)
C7	0.0741 (13)	0.0641 (12)	0.0810 (14)	−0.0287 (10)	0.0052 (11)	0.0041 (10)
C8'	0.0611 (10)	0.0385 (8)	0.0623 (11)	−0.0213 (7)	−0.0151 (8)	0.0093 (7)
C8	0.0486 (10)	0.0584 (11)	0.0983 (16)	−0.0215 (8)	−0.0032 (10)	−0.0021 (10)
C9	0.0424 (9)	0.0429 (9)	0.0794 (12)	−0.0144 (7)	−0.0114 (8)	−0.0055 (8)
C9'	0.0443 (8)	0.0348 (7)	0.0498 (9)	−0.0136 (6)	−0.0119 (7)	−0.0016 (6)
C10	0.0438 (8)	0.0472 (9)	0.0576 (10)	−0.0131 (7)	−0.0148 (7)	−0.0065 (7)
C10'	0.0432 (8)	0.0347 (7)	0.0446 (8)	−0.0140 (6)	−0.0106 (6)	−0.0026 (6)
C11'	0.0512 (9)	0.0421 (8)	0.0451 (9)	−0.0155 (7)	−0.0081 (7)	−0.0026 (7)
C11	0.0554 (10)	0.0621 (10)	0.0551 (10)	−0.0163 (8)	−0.0154 (8)	−0.0085 (8)
C12	0.0591 (12)	0.0765 (12)	0.0430 (9)	−0.0117 (9)	−0.0078 (8)	−0.0100 (8)
C12'	0.0641 (10)	0.0487 (10)	0.0432 (9)	−0.0227 (8)	−0.0044 (8)	0.0001 (7)
N13	0.0640 (11)	0.1429 (18)	0.0513 (10)	−0.0231 (11)	−0.0009 (8)	−0.0111 (10)
N13'	0.1215 (15)	0.0564 (10)	0.0620 (10)	−0.0331 (10)	−0.0029 (10)	0.0065 (8)

O1—C10	1.2190 (18)	C5—H5	0.9300
O1'—C10'	1.2173 (17)	C6'—C7'	1.389 (2)
N1—C2	1.335 (2)	C6'—H6'	0.9300
N1—C9	1.379 (2)	C6—C7	1.396 (3)
N1—H1	0.8600	C6—H6	0.9300
N1'—C2'	1.3372 (19)	C7'—C8'	1.367 (2)
N1'—C9'	1.3755 (19)	C7'—H7'	0.9300
N1'—H1'	0.8600	C7—C8	1.371 (3)
C2—C3	1.379 (2)	C7—H7	0.9300
C2—H2	0.9300	C8'—C9'	1.381 (2)
C2'—C3'	1.373 (2)	C8'—H8'	0.9300
C2'—H2'	0.9300	C8—C9	1.376 (3)
C3—C10	1.429 (2)	C8—H8	0.9300
C3—C4	1.431 (2)	C10—C11	1.517 (2)
C3'—C10'	1.4331 (19)	C10'—C11'	1.516 (2)
C3'—C4'	1.436 (2)	C11'—C12'	1.445 (2)
C4—C5	1.393 (2)	C11'—H11A	0.9700
C4—C9	1.406 (2)	C11'—H11B	0.9700
C4'—C5'	1.393 (2)	C11—C12	1.443 (3)
C4'—C9'	1.3987 (19)	C11—H11C	0.9700
C5'—C6'	1.372 (2)	C11—H11D	0.9700
C5'—H5'	0.9300	C12—N13	1.133 (2)
C5—C6	1.369 (3)	C12'—N13'	1.132 (2)
C2—N1—C9	109.94 (14)	C8'—C7'—H7'	119.4
C2—N1—H1	125.0	C6'—C7'—H7'	119.4
C9—N1—H1	125.0	C8—C7—C6	121.35 (19)
C2'—N1'—C9'	109.56 (12)	C8—C7—H7	119.3
C2'—N1'—H1'	125.2	C6—C7—H7	119.3
C9'—N1'—H1'	125.2	C7'—C8'—C9'	117.34 (15)
N1—C2—C3	109.81 (16)	C7'—C8'—H8'	121.3
N1—C2—H2	125.1	C9'—C8'—H8'	121.3
C3—C2—H2	125.1	C7—C8—C9	117.29 (18)
N1'—C2'—C3'	110.07 (14)	C7—C8—H8	121.4
N1'—C2'—H2'	125.0	C9—C8—H8	121.4
C3'—C2'—H2'	125.0	C8—C9—N1	130.03 (16)
C2—C3—C10	126.55 (16)	C8—C9—C4	122.72 (17)
C2—C3—C4	106.56 (14)	N1—C9—C4	107.25 (15)
C10—C3—C4	126.89 (14)	N1'—C9'—C8'	129.55 (14)
C2'—C3'—C10'	126.66 (14)	N1'—C9'—C4'	107.66 (13)
C2'—C3'—C4'	106.34 (12)	C8'—C9'—C4'	122.78 (14)
C10'—C3'—C4'	126.99 (13)	O1—C10—C3	122.51 (15)
C5—C4—C9	118.60 (16)	O1—C10—C11	119.87 (15)
C5—C4—C3	134.95 (15)	C3—C10—C11	117.61 (13)
C9—C4—C3	106.45 (14)	O1'—C10'—C3'	122.74 (13)
C5'—C4'—C9'	118.54 (13)	O1'—C10'—C11'	120.06 (13)
C5'—C4'—C3'	135.07 (13)	C3'—C10'—C11'	117.20 (12)
C9'—C4'—C3'	106.36 (12)	C12'—C11'—C10'	112.33 (13)
C6'—C5'—C4'	118.70 (14)	C12'—C11'—H11A	109.1
C6'—C5'—H5'	120.6	C10'—C11'—H11A	109.1
C4'—C5'—H5'	120.6	C12'—C11'—H11B	109.1
C6—C5—C4	118.94 (17)	C10'—C11'—H11B	109.1
C6—C5—H5	120.5	H11A—C11'—H11B	107.9
C4—C5—H5	120.5	C12—C11—C10	112.34 (14)
C5'—C6'—C7'	121.46 (16)	C12—C11—H11C	109.1
C5'—C6'—H6'	119.3	C10—C11—H11C	109.1
C7'—C6'—H6'	119.3	C12—C11—H11D	109.1
C5—C6—C7	121.09 (19)	C10—C11—H11D	109.1
C5—C6—H6	119.5	H11C—C11—H11D	107.9
C7—C6—H6	119.5	N13—C12—C11	179.8 (2)
C8'—C7'—C6'	121.15 (16)	N13'—C12'—C11'	179.6 (2)
C9—N1—C2—C3	0.0 (2)	C2—N1—C9—C4	0.35 (18)
C9'—N1'—C2'—C3'	0.34 (17)	C5—C4—C9—C8	−0.7 (2)
N1—C2—C3—C10	178.76 (15)	C3—C4—C9—C8	179.28 (15)
N1—C2—C3—C4	−0.41 (19)	C5—C4—C9—N1	179.39 (14)
N1'—C2'—C3'—C10'	179.69 (14)	C3—C4—C9—N1	−0.59 (17)
N1'—C2'—C3'—C4'	−0.69 (17)	C2'—N1'—C9'—C8'	179.31 (16)
C2—C3—C4—C5	−179.36 (17)	C2'—N1'—C9'—C4'	0.18 (17)
C10—C3—C4—C5	1.5 (3)	C7'—C8'—C9'—N1'	−177.93 (15)
C2—C3—C4—C9	0.61 (17)	C7'—C8'—C9'—C4'	1.1 (2)
C10—C3—C4—C9	−178.56 (15)	C5'—C4'—C9'—N1'	177.78 (13)
C2'—C3'—C4'—C5'	−177.20 (16)	C3'—C4'—C9'—N1'	−0.59 (16)
C10'—C3'—C4'—C5'	2.4 (3)	C5'—C4'—C9'—C8'	−1.4 (2)
C2'—C3'—C4'—C9'	0.78 (16)	C3'—C4'—C9'—C8'	−179.80 (14)
C10'—C3'—C4'—C9'	−179.60 (14)	C2—C3—C10—O1	−179.17 (16)
C9'—C4'—C5'—C6'	0.4 (2)	C4—C3—C10—O1	−0.2 (3)
C3'—C4'—C5'—C6'	178.23 (16)	C2—C3—C10—C11	0.1 (2)
C9—C4—C5—C6	0.2 (2)	C4—C3—C10—C11	179.09 (15)
C3—C4—C5—C6	−179.88 (17)	C2'—C3'—C10'—O1'	−179.31 (15)
C4'—C5'—C6'—C7'	0.8 (3)	C4'—C3'—C10'—O1'	1.1 (2)
C4—C5—C6—C7	0.6 (3)	C2'—C3'—C10'—C11'	−0.3 (2)
C5'—C6'—C7'—C8'	−1.2 (3)	C4'—C3'—C10'—C11'	−179.83 (13)
C5—C6—C7—C8	−0.9 (3)	O1'—C10'—C11'—C12'	−14.8 (2)
C6'—C7'—C8'—C9'	0.2 (3)	C3'—C10'—C11'—C12'	166.12 (13)
C6—C7—C8—C9	0.3 (3)	O1—C10—C11—C12	−2.2 (2)
C7—C8—C9—N1	−179.67 (17)	C3—C10—C11—C12	178.56 (15)
C7—C8—C9—C4	0.5 (3)	C10—C11—C12—N13	51 (88)
C2—N1—C9—C8	−179.50 (18)	C10'—C11'—C12'—N13'	−58 (25)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	1.98	2.8146 (18)	163
C2—H2···N13i	0.93	2.59	3.236 (2)	127
N1'—H1'···O1'ii	0.86	2.00	2.8166 (15)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	1.98	2.8146 (18)	163
C2—H2⋯N13i	0.93	2.59	3.236 (2)	127
N1′—H1′⋯O1′ii	0.86	2.00	2.8166 (15)	158

Symmetry codes: (i) ; (ii) .