1H-Indole-3-carbaldehyde

Dileep, C.S.; Abdoh, M.M.M.; Chakravarthy, M.P.; Mohana, K.N.; Sridhar, M.A.

doi:10.1107/S1600536812040573

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3135

doi:10.1107/S1600536812040573

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1H-Indole-3-carbaldehyde

C. S. Dileep,^a M. M. M. Abdoh,^b M. P. Chakravarthy,^c K. N. Mohana ^c and M. A. Sridhar ^a ^*

^aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, ^bDepartment of Physics, Faculty of Science, An Najah National University, Nabtus, West Bank, Palestinian Territories, and ^cDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India
^*Correspondence e-mail: mas@physics.uni-mysore.ac.in

(Received 14 September 2012; accepted 25 September 2012; online 13 October 2012)

In the title compound, C₉H₇NO, 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 molecules into chains which run parallel to [02-1].

Related literature

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

Experimental

Crystal data

C₉H₇NO
M_r = 145.16
Orthorhombic, P c a 2₁
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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.069
S = 1.08
775 reflections
109 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.09 e Å⁻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) $[-x+{\script{3\over 2}}, y-1, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812040573/go2070sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812040573/go2070Isup3.cml

checkCIF report

Comment top

The molecule is shown with its labelling in Figure 1. The molecules are connected into one-dimensional chains by the N1–H1A···O1(3/2-x,-1+y,1/2+z hydrogen bond which links the molecules into one dimensional chains which run parellel to [2-10], Table 1 and Figure2.

Related literature top

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

Experimental top

Indole was converted to 1H-indole-3-carbaldehyde in the presence of DMF, POCl3, NaOH. 1H-indole-3-carbaldehyde was taken and recrystallized in methanol solvent. The purity of the compound is confirmed by the TLC. A little quantity of compound was taken again for recrystallization to get a pure crystal in methanol solvent medium.

Computing details top

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 (Spek, 2009).

Figures top

	Fig. 1. ORTEP of the title compound with the ellipsoids for non-H atoms are drawn at the 50% probability.
	Fig. 2. Molecular packing view of down the b axis. Dashed lines indicate hydrogen bonds.

1H-Indole-3-carbaldehyde top

Crystal data top

C₉H₇NO	Z = 4
M_r = 145.16	F(000) = 304
Orthorhombic, Pca2₁	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0297P)² + 0.0895P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.002
775 reflections	Δρ_max = 0.11 e Å⁻³
109 parameters	Δρ_min = −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)

Crystal data top

C₉H₇NO	V = 710.24 (8) Å³
M_r = 145.16	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 14.0758 (9) Å	µ = 0.09 mm⁻¹
b = 5.8059 (4) Å	T = 293 K
c = 8.6909 (5) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	699 reflections with I > 2σ(I)
3791 measured reflections	R_int = 0.024
775 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	1 restraint
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.11 e Å⁻³
775 reflections	Δρ_min = −0.09 e Å⁻³
109 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y−1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₉H₇NO
M_r	145.16
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	14.0758 (9), 5.8059 (4), 8.6909 (5)
V (Å³)	710.24 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3791, 775, 699
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.069, 1.08
No. of reflections	775
No. of parameters	109
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.09

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y−1, z+1/2.

Acknowledgements

CSD would like to acknowledge the UGC–BRS and the University of Mysore for financial asistance.

References

Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Rizal, M. R., Ali, H. M. & Ng, S. W. (2008). Acta Cryst. E64, o555. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar