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ISSN: 2056-9890

1H-Indole-3-carbaldehyde

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[Rizal, M. R., Ali, H. M. & Ng, S. W. (2008). Acta Cryst. E64, o555.]).

[Scheme 1]

Experimental

Crystal data
  • C9H7NO

  • Mr = 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)

  • Rint = 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

  • Δρmax = 0.11 e Å−3

  • Δρmin = −0.09 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009)[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]; software used to prepare material for publication: PLATON[Spek, A. L. (2009). Acta Cryst. D65, 148-155.].

Supporting information


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.

Refinement top

H atoms were treated as riding atoms with C—H(aromatic), 0.93 Å with Uiso = 1.2Ueq(C). The H atoms attached to C1 and N1 were located on a difference map and refined isotropically. Friedel pairs were merged.

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
[Figure 1] Fig. 1. ORTEP of the title compound with the ellipsoids for non-H atoms are drawn at the 50% probability.
[Figure 2] Fig. 2. Molecular packing view of down the b axis. Dashed lines indicate hydrogen bonds.
1H-Indole-3-carbaldehyde top
Crystal data top
C9H7NOZ = 4
Mr = 145.16F(000) = 304
Orthorhombic, Pca21Dx = 1.357 Mg m3
Hall symbol: P 2c -2acMo Kα radiation, λ = 0.71073 Å
a = 14.0758 (9) ŵ = 0.09 mm1
b = 5.8059 (4) ÅT = 293 K
c = 8.6909 (5) ÅBlock, colourless
V = 710.24 (8) Å30.30 × 0.20 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
699 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 26.5°, θmin = 2.9°
ω and ϕ scanh = 1716
3791 measured reflectionsk = 67
775 independent reflectionsl = 108
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H 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 reflectionsΔρmax = 0.11 e Å3
109 parametersΔρmin = 0.09 e Å3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.031 (5)
Crystal data top
C9H7NOV = 710.24 (8) Å3
Mr = 145.16Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 14.0758 (9) ŵ = 0.09 mm1
b = 5.8059 (4) ÅT = 293 K
c = 8.6909 (5) Å0.30 × 0.20 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
699 reflections with I > 2σ(I)
3791 measured reflectionsRint = 0.024
775 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0291 restraint
wR(F2) = 0.069H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.11 e Å3
775 reflectionsΔρmin = 0.09 e Å3
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
xyzUiso*/Ueq
C10.76788 (16)0.4092 (3)0.0642 (3)0.0443 (5)
C20.72368 (14)0.2453 (4)0.0341 (3)0.0401 (5)
C30.76781 (17)0.0501 (4)0.0871 (3)0.0489 (6)
H30.82970.00740.06280.059*
C40.62446 (14)0.0451 (3)0.1907 (3)0.0418 (5)
C50.54556 (17)0.0080 (4)0.2797 (3)0.0500 (6)
H50.54270.14300.33710.060*
C60.47250 (16)0.1462 (4)0.2795 (3)0.0535 (6)
H60.41890.11660.33880.064*
C70.47646 (15)0.3467 (4)0.1924 (3)0.0526 (6)
H70.42550.44870.19510.063*
C80.55405 (16)0.3976 (4)0.1024 (3)0.0449 (5)
H80.55550.53100.04330.054*
C90.63026 (14)0.2450 (3)0.1019 (2)0.0370 (5)
N10.70988 (14)0.0700 (3)0.1783 (2)0.0510 (5)
O10.72964 (12)0.5795 (2)0.1176 (2)0.0565 (5)
H10.8360 (16)0.376 (4)0.086 (3)0.054 (6)*
H1A0.7253 (17)0.204 (4)0.233 (4)0.073 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0516 (13)0.0432 (10)0.0382 (12)0.0002 (9)0.0027 (11)0.0014 (10)
C20.0514 (11)0.0368 (9)0.0323 (10)0.0032 (9)0.0004 (9)0.0009 (8)
C30.0557 (14)0.0476 (11)0.0435 (14)0.0109 (11)0.0050 (11)0.0022 (10)
C40.0557 (12)0.0341 (9)0.0354 (11)0.0017 (8)0.0038 (10)0.0013 (10)
C50.0666 (14)0.0435 (12)0.0399 (13)0.0135 (11)0.0021 (12)0.0050 (10)
C60.0499 (13)0.0624 (14)0.0484 (14)0.0136 (11)0.0036 (11)0.0011 (12)
C70.0466 (12)0.0576 (13)0.0536 (15)0.0036 (10)0.0017 (12)0.0041 (14)
C80.0512 (12)0.0406 (10)0.0428 (13)0.0013 (9)0.0046 (11)0.0037 (9)
C90.0473 (11)0.0344 (10)0.0293 (10)0.0027 (8)0.0052 (9)0.0017 (8)
N10.0680 (12)0.0395 (9)0.0455 (11)0.0102 (8)0.0016 (10)0.0113 (10)
O10.0658 (11)0.0442 (8)0.0596 (11)0.0002 (7)0.0058 (8)0.0163 (8)
Geometric parameters (Å, º) top
C1—O11.218 (2)C5—C61.363 (3)
C1—C21.422 (3)C5—H50.9300
C1—H11.00 (2)C6—C71.390 (3)
C2—C31.372 (3)C6—H60.9300
C2—C91.441 (3)C7—C81.375 (3)
C3—N11.334 (3)C7—H70.9300
C3—H30.9300C8—C91.391 (3)
C4—N11.380 (3)C8—H80.9300
C4—C51.388 (3)N1—H1A0.94 (2)
C4—C91.396 (3)
O1—C1—C2125.4 (2)C5—C6—C7121.4 (2)
O1—C1—H1120.6 (14)C5—C6—H6119.3
C2—C1—H1114.0 (14)C7—C6—H6119.3
C3—C2—C1123.8 (2)C8—C7—C6121.4 (2)
C3—C2—C9105.93 (19)C8—C7—H7119.3
C1—C2—C9130.22 (19)C6—C7—H7119.3
N1—C3—C2110.8 (2)C7—C8—C9118.5 (2)
N1—C3—H3124.6C7—C8—H8120.7
C2—C3—H3124.6C9—C8—H8120.7
N1—C4—C5129.30 (19)C8—C9—C4118.84 (19)
N1—C4—C9107.95 (18)C8—C9—C2134.75 (19)
C5—C4—C9122.65 (19)C4—C9—C2106.31 (18)
C6—C5—C4117.2 (2)C3—N1—C4109.04 (17)
C6—C5—H5121.4C3—N1—H1A126.4 (16)
C4—C5—H5121.4C4—N1—H1A124.4 (16)
O1—C1—C2—C3177.2 (2)N1—C4—C9—C8176.6 (2)
O1—C1—C2—C94.9 (4)C5—C4—C9—C80.1 (3)
C1—C2—C3—N1179.3 (2)N1—C4—C9—C20.2 (2)
C9—C2—C3—N11.0 (3)C5—C4—C9—C2176.9 (2)
N1—C4—C5—C6175.0 (2)C3—C2—C9—C8175.3 (2)
C9—C4—C5—C60.9 (3)C1—C2—C9—C82.8 (4)
C4—C5—C6—C70.7 (4)C3—C2—C9—C40.7 (2)
C5—C6—C7—C80.3 (4)C1—C2—C9—C4178.9 (2)
C6—C7—C8—C91.1 (3)C2—C3—N1—C40.8 (3)
C7—C8—C9—C40.9 (3)C5—C4—N1—C3176.0 (2)
C7—C8—C9—C2174.8 (2)C9—C4—N1—C30.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.94 (3)1.92 (3)2.831 (2)165 (3)
Symmetry code: (i) x+3/2, y1, z+1/2.

Experimental details

Crystal data
Chemical formulaC9H7NO
Mr145.16
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)293
a, b, c (Å)14.0758 (9), 5.8059 (4), 8.6909 (5)
V3)710.24 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3791, 775, 699
Rint0.024
(sin θ/λ)max1)0.627
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.069, 1.08
No. of reflections775
No. of parameters109
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N1—H1A···O1i0.94 (3)1.92 (3)2.831 (2)165 (3)
Symmetry code: (i) x+3/2, y1, z+1/2.
 

Acknowledgements

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

References

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

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COMMUNICATIONS
ISSN: 2056-9890
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