organic compounds
5-Methyl-1H-indole-3-carbaldehyde
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: hamid.khaledi@gmail.com
The title molecule, C10H9NO, is almost planar with an r.m.s. deviation for all non-H atoms of 0.0115 Å. In the crystal, molecules are connected through N—H⋯O hydrogen bonds into chains running along [021]. The chains are further connected via C—H⋯π interactions, forming layers in the bc plane.
Related literature
For the structure of 1H-indole-3-carbaldehyde, see: Ng (2007) and for the structure of 6-bromo-1H-indole-3-carbaldehyde, see: Johnson et al. (2009).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536812034873/zl2498sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812034873/zl2498Isup2.hkl
The title crystals were obtained by slow evaporation of an ethanolic solution of the commercially available 5-methylindole-3-carboxaldehyde at room temperature.
The C-bound hydrogen atoms were located in calculated positions and refined in a riding mode with C—H distances of 0.93 (Csp2) and 0.96 (Cmethyl) Å. The N-bound H atom was found in a difference Fourier map and refined freely. For all hydrogen atoms, Uiso were set to 1.2–1.5Ueq(carrier atom). In the absence of significant
effects Friedel pairs were merged.Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).C10H9NO | F(000) = 336 |
Mr = 159.18 | Dx = 1.267 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 1172 reflections |
a = 16.9456 (19) Å | θ = 2.4–22.1° |
b = 5.7029 (6) Å | µ = 0.08 mm−1 |
c = 8.6333 (9) Å | T = 296 K |
V = 834.31 (15) Å3 | Lath, yellow |
Z = 4 | 0.47 × 0.15 × 0.05 mm |
Bruker APEXII CCD diffractometer | 1147 independent reflections |
Radiation source: fine-focus sealed tube | 717 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ϕ and ω scans | θmax = 28.8°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −22→13 |
Tmin = 0.962, Tmax = 0.996 | k = −7→7 |
5499 measured reflections | l = −11→11 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0596P)2] where P = (Fo2 + 2Fc2)/3 |
1147 reflections | (Δ/σ)max < 0.001 |
113 parameters | Δρmax = 0.12 e Å−3 |
1 restraint | Δρmin = −0.14 e Å−3 |
C10H9NO | V = 834.31 (15) Å3 |
Mr = 159.18 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 16.9456 (19) Å | µ = 0.08 mm−1 |
b = 5.7029 (6) Å | T = 296 K |
c = 8.6333 (9) Å | 0.47 × 0.15 × 0.05 mm |
Bruker APEXII CCD diffractometer | 1147 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 717 reflections with I > 2σ(I) |
Tmin = 0.962, Tmax = 0.996 | Rint = 0.039 |
5499 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 1 restraint |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | Δρmax = 0.12 e Å−3 |
1147 reflections | Δρmin = −0.14 e Å−3 |
113 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 | ||
O1 | 0.27204 (11) | 1.0610 (3) | 0.6573 (2) | 0.0742 (6) | |
N1 | 0.29282 (16) | 0.4126 (4) | 0.3481 (3) | 0.0760 (7) | |
H1N | 0.2766 (15) | 0.285 (5) | 0.290 (5) | 0.091* | |
C1 | 0.2435 (2) | 0.5303 (4) | 0.4384 (3) | 0.0717 (8) | |
H1 | 0.1913 | 0.4879 | 0.4563 | 0.086* | |
C2 | 0.27969 (14) | 0.7233 (4) | 0.5018 (3) | 0.0587 (6) | |
C3 | 0.35916 (14) | 0.7227 (4) | 0.4414 (3) | 0.0535 (6) | |
C4 | 0.42432 (15) | 0.8710 (4) | 0.4561 (3) | 0.0554 (6) | |
H4 | 0.4212 | 1.0036 | 0.5185 | 0.066* | |
C5 | 0.49316 (16) | 0.8208 (4) | 0.3782 (3) | 0.0638 (7) | |
C6 | 0.49673 (18) | 0.6225 (5) | 0.2839 (4) | 0.0785 (8) | |
H6 | 0.5434 | 0.5904 | 0.2311 | 0.094* | |
C7 | 0.4341 (2) | 0.4736 (5) | 0.2661 (3) | 0.0766 (8) | |
H7 | 0.4377 | 0.3422 | 0.2026 | 0.092* | |
C8 | 0.36502 (18) | 0.5241 (4) | 0.3453 (3) | 0.0626 (7) | |
C9 | 0.24192 (16) | 0.8851 (4) | 0.6026 (3) | 0.0640 (6) | |
H9 | 0.1897 | 0.8544 | 0.6292 | 0.077* | |
C10 | 0.56347 (18) | 0.9773 (6) | 0.3966 (4) | 0.0860 (10) | |
H10A | 0.5654 | 1.0866 | 0.3121 | 0.129* | |
H10B | 0.6107 | 0.8842 | 0.3969 | 0.129* | |
H10C | 0.5595 | 1.0615 | 0.4926 | 0.129* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0843 (15) | 0.0640 (9) | 0.0743 (12) | 0.0106 (9) | 0.0086 (10) | −0.0101 (9) |
N1 | 0.109 (2) | 0.0565 (10) | 0.0622 (13) | −0.0129 (12) | −0.0146 (15) | −0.0053 (11) |
C1 | 0.0820 (19) | 0.0660 (13) | 0.0671 (17) | −0.0143 (15) | −0.0109 (17) | 0.0081 (14) |
C2 | 0.0722 (18) | 0.0533 (11) | 0.0508 (12) | −0.0012 (11) | −0.0030 (12) | 0.0033 (10) |
C3 | 0.0668 (17) | 0.0499 (10) | 0.0440 (11) | 0.0056 (10) | −0.0070 (11) | −0.0013 (10) |
C4 | 0.0639 (16) | 0.0528 (10) | 0.0495 (12) | 0.0026 (11) | −0.0052 (12) | −0.0003 (10) |
C5 | 0.0640 (18) | 0.0699 (14) | 0.0575 (14) | 0.0141 (12) | −0.0022 (13) | 0.0073 (13) |
C6 | 0.081 (2) | 0.0869 (18) | 0.0678 (16) | 0.0295 (15) | 0.0074 (16) | 0.0032 (15) |
C7 | 0.105 (2) | 0.0657 (14) | 0.0590 (16) | 0.0237 (16) | 0.0008 (17) | −0.0133 (12) |
C8 | 0.089 (2) | 0.0488 (10) | 0.0502 (13) | 0.0051 (12) | −0.0112 (14) | −0.0021 (11) |
C9 | 0.0662 (17) | 0.0683 (13) | 0.0574 (14) | 0.0083 (14) | 0.0013 (13) | 0.0124 (13) |
C10 | 0.068 (2) | 0.102 (2) | 0.088 (2) | 0.0008 (17) | 0.0032 (16) | 0.0136 (17) |
O1—C9 | 1.221 (3) | C4—H4 | 0.9300 |
N1—C1 | 1.326 (4) | C5—C6 | 1.395 (4) |
N1—C8 | 1.379 (4) | C5—C10 | 1.497 (4) |
N1—H1N | 0.93 (3) | C6—C7 | 1.368 (4) |
C1—C2 | 1.374 (3) | C6—H6 | 0.9300 |
C1—H1 | 0.9300 | C7—C8 | 1.385 (4) |
C2—C9 | 1.421 (3) | C7—H7 | 0.9300 |
C2—C3 | 1.444 (3) | C9—H9 | 0.9300 |
C3—C4 | 1.397 (3) | C10—H10A | 0.9600 |
C3—C8 | 1.408 (3) | C10—H10B | 0.9600 |
C4—C5 | 1.377 (3) | C10—H10C | 0.9600 |
C1—N1—C8 | 109.7 (2) | C7—C6—C5 | 122.3 (3) |
C1—N1—H1N | 121.9 (18) | C7—C6—H6 | 118.8 |
C8—N1—H1N | 128.1 (18) | C5—C6—H6 | 118.8 |
N1—C1—C2 | 111.0 (3) | C6—C7—C8 | 118.1 (2) |
N1—C1—H1 | 124.5 | C6—C7—H7 | 121.0 |
C2—C1—H1 | 124.5 | C8—C7—H7 | 121.0 |
C1—C2—C9 | 124.3 (3) | N1—C8—C7 | 131.4 (2) |
C1—C2—C3 | 105.7 (2) | N1—C8—C3 | 107.3 (2) |
C9—C2—C3 | 130.0 (2) | C7—C8—C3 | 121.2 (3) |
C4—C3—C8 | 119.0 (2) | O1—C9—C2 | 125.6 (3) |
C4—C3—C2 | 134.7 (2) | O1—C9—H9 | 117.2 |
C8—C3—C2 | 106.3 (2) | C2—C9—H9 | 117.2 |
C5—C4—C3 | 120.0 (2) | C5—C10—H10A | 109.5 |
C5—C4—H4 | 120.0 | C5—C10—H10B | 109.5 |
C3—C4—H4 | 120.0 | H10A—C10—H10B | 109.5 |
C4—C5—C6 | 119.4 (3) | C5—C10—H10C | 109.5 |
C4—C5—C10 | 119.9 (2) | H10A—C10—H10C | 109.5 |
C6—C5—C10 | 120.7 (3) | H10B—C10—H10C | 109.5 |
Cg is the centroid of the N1/C1/C2/C3/C8 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.93 (3) | 1.90 (3) | 2.818 (3) | 169 (3) |
C9—H9···Cgii | 0.93 | 2.91 | 3.312 (3) | 107 |
Symmetry codes: (i) −x+1/2, y−1, z−1/2; (ii) −x+1/2, y, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H9NO |
Mr | 159.18 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 296 |
a, b, c (Å) | 16.9456 (19), 5.7029 (6), 8.6333 (9) |
V (Å3) | 834.31 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.47 × 0.15 × 0.05 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.962, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5499, 1147, 717 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.677 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.107, 0.98 |
No. of reflections | 1147 |
No. of parameters | 113 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.12, −0.14 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).
Cg is the centroid of the N1/C1/C2/C3/C8 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.93 (3) | 1.90 (3) | 2.818 (3) | 169 (3) |
C9—H9···Cgii | 0.93 | 2.91 | 3.312 (3) | 107 |
Symmetry codes: (i) −x+1/2, y−1, z−1/2; (ii) −x+1/2, y, z+1/2. |
Acknowledgements
We thank the University of Malaya for funding this study (UMRG grant No. RG 066/12BIO).
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Johnson, J. E., Canseco, D. C., Dolliver, D. D., Schetz, J. A. & Fronczek, F. R. (2009). J. Chem. Crystallogr. 39, 329–336. Web of Science CSD CrossRef CAS Google Scholar
Ng, S. W. (2007). Acta Cryst. E63, o2732. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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The structure of the title compound is isomorphous with that of 1H-indole-3-carbaldehyde (Ng, 2007). The planar molecules are connected via N—H···O hydrogen bonds (Table 1) into chains in the [021] direction. The chains are further linked through C—H···π interactions (Table 1) to form layers in the bc plane. The structure of 6-bromo-1H-indole-3-carbaldehyde (Johnson et al., 2009) exhibits similar N—H···O bonded chains, however, further supramolecular aggregation by Br-involved interactions is observed.