organic compounds
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
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].
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell 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
10.1107/S1600536812040573/go2070sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812040573/go2070Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812040573/go2070Isup3.cml
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.
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.
Data collection: APEX2 (Bruker, 2004); cell
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).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. |
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) |
C9H7NO | V = 710.24 (8) Å3 |
Mr = 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 |
Bruker Kappa APEXII CCD diffractometer | 699 reflections with I > 2σ(I) |
3791 measured reflections | Rint = 0.024 |
775 independent reflections |
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 | Δρmax = 0.11 e Å−3 |
775 reflections | Δρmin = −0.09 e Å−3 |
109 parameters |
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) |
Symmetry code: (i) −x+3/2, y−1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C9H7NO |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (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).
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
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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.