1H-Indole-3-carbaldehyde.

In the title compound, C(9)H(7)NO, the benzene ring forms a dihedral angle of 3.98 (12)° with the pyrrole ring. In the crystal, N-H⋯O hydrogen bonds links the mol-ecules into chains which run parallel to [02-1].

Related literature

For a related structure, see: Rizal et al. (2008 ▶).

Experimental

Crystal data

C9H7NO

M = 145.16

Orthorhombic,

a = 14.0758 (9) Å

b = 5.8059 (4) Å

c = 8.6909 (5) Å

V = 710.24 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

3791 measured reflections

775 independent reflections

699 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.069

S = 1.08

775 reflections

109 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.11 e Å−3

Δρmin = −0.09 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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: PLATON ▶.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812040573/go2070sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040573/go2070Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812040573/go2070Isup3.cml

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

C9H7NO	Z = 4
Mr = 145.16	F(000) = 304
Orthorhombic, Pca21	Dx = 1.357 Mg m−3
Hall symbol: P 2c -2ac	Mo Kα radiation, λ = 0.71073 Å
a = 14.0758 (9) Å	µ = 0.09 mm−1
b = 5.8059 (4) Å	T = 293 K
c = 8.6909 (5) Å	Block, colourless
V = 710.24 (8) Å3	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	699 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 26.5°, θmin = 2.9°
ω and φ scan	h = −17→16
3791 measured reflections	k = −6→7
775 independent reflections	l = −10→8

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.069	w = 1/[σ2(Fo2) + (0.0297P)2 + 0.0895P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.002
775 reflections	Δρmax = 0.11 e Å−3
109 parameters	Δρmin = −0.09 e Å−3
1 restraint	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.031 (5)

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	0.76788 (16)	0.4092 (3)	−0.0642 (3)	0.0443 (5)
C2	0.72368 (14)	0.2453 (4)	0.0341 (3)	0.0401 (5)
C3	0.76781 (17)	0.0501 (4)	0.0871 (3)	0.0489 (6)
H3	0.8297	0.0074	0.0628	0.059*
C4	0.62446 (14)	0.0451 (3)	0.1907 (3)	0.0418 (5)
C5	0.54556 (17)	−0.0080 (4)	0.2797 (3)	0.0500 (6)
H5	0.5427	−0.1430	0.3371	0.060*
C6	0.47250 (16)	0.1462 (4)	0.2795 (3)	0.0535 (6)
H6	0.4189	0.1166	0.3388	0.064*
C7	0.47646 (15)	0.3467 (4)	0.1924 (3)	0.0526 (6)
H7	0.4255	0.4487	0.1951	0.063*
C8	0.55405 (16)	0.3976 (4)	0.1024 (3)	0.0449 (5)
H8	0.5555	0.5310	0.0433	0.054*
C9	0.63026 (14)	0.2450 (3)	0.1019 (2)	0.0370 (5)
N1	0.70988 (14)	−0.0700 (3)	0.1783 (2)	0.0510 (5)
O1	0.72964 (12)	0.5795 (2)	−0.1176 (2)	0.0565 (5)
H1	0.8360 (16)	0.376 (4)	−0.086 (3)	0.054 (6)*
H1A	0.7253 (17)	−0.204 (4)	0.233 (4)	0.073 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0516 (13)	0.0432 (10)	0.0382 (12)	−0.0002 (9)	0.0027 (11)	−0.0014 (10)
C2	0.0514 (11)	0.0368 (9)	0.0323 (10)	0.0032 (9)	0.0004 (9)	0.0009 (8)
C3	0.0557 (14)	0.0476 (11)	0.0435 (14)	0.0109 (11)	0.0050 (11)	0.0022 (10)
C4	0.0557 (12)	0.0341 (9)	0.0354 (11)	−0.0017 (8)	−0.0038 (10)	0.0013 (10)
C5	0.0666 (14)	0.0435 (12)	0.0399 (13)	−0.0135 (11)	−0.0021 (12)	0.0050 (10)
C6	0.0499 (13)	0.0624 (14)	0.0484 (14)	−0.0136 (11)	0.0036 (11)	−0.0011 (12)
C7	0.0466 (12)	0.0576 (13)	0.0536 (15)	0.0036 (10)	−0.0017 (12)	−0.0041 (14)
C8	0.0512 (12)	0.0406 (10)	0.0428 (13)	0.0013 (9)	−0.0046 (11)	0.0037 (9)
C9	0.0473 (11)	0.0344 (10)	0.0293 (10)	−0.0027 (8)	−0.0052 (9)	−0.0017 (8)
N1	0.0680 (12)	0.0395 (9)	0.0455 (11)	0.0102 (8)	0.0016 (10)	0.0113 (10)
O1	0.0658 (11)	0.0442 (8)	0.0596 (11)	−0.0002 (7)	0.0058 (8)	0.0163 (8)

C1—O1	1.218 (2)	C5—C6	1.363 (3)
C1—C2	1.422 (3)	C5—H5	0.9300
C1—H1	1.00 (2)	C6—C7	1.390 (3)
C2—C3	1.372 (3)	C6—H6	0.9300
C2—C9	1.441 (3)	C7—C8	1.375 (3)
C3—N1	1.334 (3)	C7—H7	0.9300
C3—H3	0.9300	C8—C9	1.391 (3)
C4—N1	1.380 (3)	C8—H8	0.9300
C4—C5	1.388 (3)	N1—H1A	0.94 (2)
C4—C9	1.396 (3)
O1—C1—C2	125.4 (2)	C5—C6—C7	121.4 (2)
O1—C1—H1	120.6 (14)	C5—C6—H6	119.3
C2—C1—H1	114.0 (14)	C7—C6—H6	119.3
C3—C2—C1	123.8 (2)	C8—C7—C6	121.4 (2)
C3—C2—C9	105.93 (19)	C8—C7—H7	119.3
C1—C2—C9	130.22 (19)	C6—C7—H7	119.3
N1—C3—C2	110.8 (2)	C7—C8—C9	118.5 (2)
N1—C3—H3	124.6	C7—C8—H8	120.7
C2—C3—H3	124.6	C9—C8—H8	120.7
N1—C4—C5	129.30 (19)	C8—C9—C4	118.84 (19)
N1—C4—C9	107.95 (18)	C8—C9—C2	134.75 (19)
C5—C4—C9	122.65 (19)	C4—C9—C2	106.31 (18)
C6—C5—C4	117.2 (2)	C3—N1—C4	109.04 (17)
C6—C5—H5	121.4	C3—N1—H1A	126.4 (16)
C4—C5—H5	121.4	C4—N1—H1A	124.4 (16)
O1—C1—C2—C3	177.2 (2)	N1—C4—C9—C8	−176.6 (2)
O1—C1—C2—C9	−4.9 (4)	C5—C4—C9—C8	0.1 (3)
C1—C2—C3—N1	179.3 (2)	N1—C4—C9—C2	0.2 (2)
C9—C2—C3—N1	1.0 (3)	C5—C4—C9—C2	176.9 (2)
N1—C4—C5—C6	175.0 (2)	C3—C2—C9—C8	175.3 (2)
C9—C4—C5—C6	−0.9 (3)	C1—C2—C9—C8	−2.8 (4)
C4—C5—C6—C7	0.7 (4)	C3—C2—C9—C4	−0.7 (2)
C5—C6—C7—C8	0.3 (4)	C1—C2—C9—C4	−178.9 (2)
C6—C7—C8—C9	−1.1 (3)	C2—C3—N1—C4	−0.8 (3)
C7—C8—C9—C4	0.9 (3)	C5—C4—N1—C3	−176.0 (2)
C7—C8—C9—C2	−174.8 (2)	C9—C4—N1—C3	0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.94 (3)	1.92 (3)	2.831 (2)	165 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.94 (3)	1.92 (3)	2.831 (2)	165 (3)

Symmetry code: (i) .