1-Vinyl-1H-indole-3-carbaldehyde.

In the title compound, C(11)H(9)NO, the C and O atoms of the attached carbaldehyde group deviate by just 0.052 (2) and 0.076 (1) Å, respectively, from the mean plane of the indole ring system. In addition to van der Waals forces, the mol-ecular packing is stabilized by C-H⋯O hydrogen bonds, which form a C(7) chain motif, and π-π inter-actions (centroid-centroid distance 3.637 Å) between the pyrrole and benzene rings of the indole ring system.

Related literature

For related literature, see: Padwa et al. (1999 ▶); Mathiesen et al. (2005 ▶); Grinev et al. (1984 ▶); Gadaginamath & Patil (1999 ▶); Rodriguez et al. (1985 ▶); Karthick et al. (2005 ▶); Selvanayagam et al. (2005 ▶); Sonar et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H9NO

M = 171.19

Monoclinic,

a = 8.3200 (5) Å

b = 8.1490 (5) Å

c = 13.1620 (7) Å

β = 99.952 (1)°

V = 878.95 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

9730 measured reflections

2072 independent reflections

1823 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.127

S = 1.05

2072 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680801547X/bt2714sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801547X/bt2714Isup2.hkl

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

C11H9NO	F000 = 360
Mr = 171.19	Dx = 1.294 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4554 reflections
a = 8.3200 (5) Å	θ = 2.1–23.6º
b = 8.1490 (5) Å	µ = 0.08 mm−1
c = 13.1620 (7) Å	T = 293 (2) K
β = 99.952 (1)º	Block, colourless
V = 878.95 (9) Å3	0.24 × 0.22 × 0.20 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	1823 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Monochromator: graphite	θmax = 28.0º
T = 293(2) K	θmin = 3.0º
ω scans	h = −10→10
Absorption correction: none	k = −10→10
9730 measured reflections	l = −17→16
2072 independent reflections

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0665P)2 + 0.1375P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2072 reflections	Δρmax = 0.21 e Å−3
118 parameters	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.81283 (15)	0.20464 (18)	−0.13362 (9)	0.0826 (4)
N1	0.41791 (12)	0.24005 (13)	0.07004 (7)	0.0469 (3)
C1	0.54641 (14)	0.14623 (13)	0.12226 (8)	0.0424 (3)
C2	0.56155 (16)	0.06833 (16)	0.21713 (9)	0.0505 (3)
H2	0.4800	0.0748	0.2572	0.061*
C3	0.70276 (18)	−0.01899 (17)	0.24918 (10)	0.0581 (3)
H3	0.7166	−0.0736	0.3121	0.070*
C4	0.82544 (17)	−0.02764 (17)	0.18966 (11)	0.0594 (4)
H4	0.9197	−0.0870	0.2139	0.071*
C5	0.80997 (15)	0.04980 (16)	0.09564 (10)	0.0527 (3)
H5	0.8925	0.0434	0.0563	0.063*
C6	0.66781 (14)	0.13815 (13)	0.06061 (8)	0.0431 (3)
C7	0.60762 (15)	0.23003 (15)	−0.03148 (9)	0.0480 (3)
C8	0.45684 (16)	0.28725 (16)	−0.02188 (9)	0.0503 (3)
H8	0.3901	0.3497	−0.0712	0.060*
C9	0.27187 (17)	0.27412 (19)	0.10596 (12)	0.0615 (4)
H9	0.2701	0.2521	0.1751	0.074*
C10	0.14066 (19)	0.3327 (2)	0.05257 (15)	0.0779 (5)
H10A	0.1365	0.3567	−0.0169	0.094*
H10B	0.0498	0.3511	0.0834	0.094*
C11	0.68162 (19)	0.2565 (2)	−0.12120 (11)	0.0621 (4)
H11	0.6233	0.3191	−0.1742	0.075*

	U11	U22	U33	U12	U13	U23
O1	0.0720 (7)	0.1185 (10)	0.0649 (7)	0.0021 (6)	0.0336 (6)	0.0075 (6)
N1	0.0474 (5)	0.0518 (6)	0.0428 (5)	0.0032 (4)	0.0110 (4)	−0.0026 (4)
C1	0.0457 (6)	0.0418 (5)	0.0396 (5)	−0.0022 (4)	0.0075 (4)	−0.0069 (4)
C2	0.0595 (7)	0.0521 (7)	0.0417 (6)	−0.0035 (5)	0.0136 (5)	−0.0023 (5)
C3	0.0707 (8)	0.0549 (7)	0.0464 (6)	0.0007 (6)	0.0035 (6)	0.0051 (5)
C4	0.0562 (7)	0.0544 (7)	0.0641 (8)	0.0080 (6)	0.0011 (6)	0.0007 (6)
C5	0.0475 (6)	0.0527 (7)	0.0591 (7)	0.0000 (5)	0.0129 (5)	−0.0070 (5)
C6	0.0472 (6)	0.0418 (6)	0.0411 (5)	−0.0053 (4)	0.0102 (4)	−0.0072 (4)
C7	0.0543 (7)	0.0486 (6)	0.0425 (6)	−0.0046 (5)	0.0124 (5)	−0.0023 (5)
C8	0.0566 (7)	0.0513 (7)	0.0427 (6)	0.0017 (5)	0.0079 (5)	0.0021 (5)
C9	0.0564 (8)	0.0736 (9)	0.0586 (8)	0.0089 (6)	0.0209 (6)	−0.0013 (6)
C10	0.0580 (9)	0.0892 (12)	0.0894 (12)	0.0170 (8)	0.0205 (8)	0.0036 (9)
C11	0.0670 (8)	0.0743 (9)	0.0481 (7)	−0.0059 (7)	0.0185 (6)	0.0041 (6)

O1—C11	1.2079 (19)	C5—C6	1.3933 (17)
N1—C8	1.3610 (16)	C5—H5	0.9300
N1—C1	1.3949 (15)	C6—C7	1.4390 (17)
N1—C9	1.4055 (16)	C7—C8	1.3645 (18)
C1—C2	1.3869 (16)	C7—C11	1.4393 (18)
C1—C6	1.4023 (16)	C8—H8	0.9300
C2—C3	1.3760 (19)	C9—C10	1.284 (2)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.392 (2)	C10—H10A	0.9300
C3—H3	0.9300	C10—H10B	0.9300
C4—C5	1.3751 (19)	C11—H11	0.9300
C4—H4	0.9300
C8—N1—C1	108.24 (10)	C5—C6—C1	119.20 (11)
C8—N1—C9	126.55 (12)	C5—C6—C7	134.39 (11)
C1—N1—C9	125.17 (11)	C1—C6—C7	106.40 (10)
C2—C1—N1	129.57 (11)	C8—C7—C6	106.95 (10)
C2—C1—C6	122.48 (11)	C8—C7—C11	123.72 (13)
N1—C1—C6	107.94 (10)	C6—C7—C11	129.29 (12)
C3—C2—C1	116.91 (12)	N1—C8—C7	110.46 (11)
C3—C2—H2	121.5	N1—C8—H8	124.8
C1—C2—H2	121.5	C7—C8—H8	124.8
C2—C3—C4	121.60 (12)	C10—C9—N1	126.30 (15)
C2—C3—H3	119.2	C10—C9—H9	116.8
C4—C3—H3	119.2	N1—C9—H9	116.8
C5—C4—C3	121.31 (12)	C9—C10—H10A	120.0
C5—C4—H4	119.3	C9—C10—H10B	120.0
C3—C4—H4	119.3	H10A—C10—H10B	120.0
C4—C5—C6	118.49 (12)	O1—C11—C7	125.68 (15)
C4—C5—H5	120.8	O1—C11—H11	117.2
C6—C5—H5	120.8	C7—C11—H11	117.2
C8—N1—C1—C2	−178.34 (12)	N1—C1—C6—C7	−0.32 (12)
C9—N1—C1—C2	−0.3 (2)	C5—C6—C7—C8	178.96 (13)
C8—N1—C1—C6	0.77 (13)	C1—C6—C7—C8	−0.24 (13)
C9—N1—C1—C6	178.86 (12)	C5—C6—C7—C11	1.3 (2)
N1—C1—C2—C3	178.96 (11)	C1—C6—C7—C11	−177.94 (13)
C6—C1—C2—C3	−0.04 (18)	C1—N1—C8—C7	−0.95 (14)
C1—C2—C3—C4	0.56 (19)	C9—N1—C8—C7	−179.00 (12)
C2—C3—C4—C5	−0.6 (2)	C6—C7—C8—N1	0.73 (14)
C3—C4—C5—C6	0.0 (2)	C11—C7—C8—N1	178.60 (12)
C4—C5—C6—C1	0.47 (17)	C8—N1—C9—C10	11.7 (3)
C4—C5—C6—C7	−178.65 (12)	C1—N1—C9—C10	−166.00 (16)
C2—C1—C6—C5	−0.47 (17)	C8—C7—C11—O1	−178.09 (15)
N1—C1—C6—C5	−179.66 (10)	C6—C7—C11—O1	−0.7 (3)
C2—C1—C6—C7	178.87 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1i	0.93	2.51	3.390 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1i	0.93	2.51	3.390 (2)	159

Symmetry code: (i) .