organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

5-Methyl-1H-indole-3-carbaldehyde

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: hamid.khaledi@gmail.com

(Received 4 August 2012; accepted 7 August 2012; online 11 August 2012)

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[Ng, S. W. (2007). Acta Cryst. E63, o2732.]) and for the structure of 6-bromo-1H-indole-3-carbaldehyde, see: Johnson et al. (2009[Johnson, J. E., Canseco, D. C., Dolliver, D. D., Schetz, J. A. & Fronczek, F. R. (2009). J. Chem. Crystallogr. 39, 329-336.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9NO

  • Mr = 159.18

  • Orthorhombic, P c a 21

  • a = 16.9456 (19) Å

  • b = 5.7029 (6) Å

  • c = 8.6333 (9) Å

  • V = 834.31 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.47 × 0.15 × 0.05 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.962, Tmax = 0.996

  • 5499 measured reflections

  • 1147 independent reflections

  • 717 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.107

  • S = 0.98

  • 1147 reflections

  • 113 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.12 e Å−3

  • Δρmin = −0.14 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N1/C1/C2/C3/C8 ring.

D—H⋯A D—H H⋯A DA 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+{\script{1\over 2}}, y-1, z-{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

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.

Related literature top

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 top

The title crystals were obtained by slow evaporation of an ethanolic solution of the commercially available 5-methylindole-3-carboxaldehyde at room temperature.

Refinement top

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 anomalous scattering effects Friedel pairs were merged.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing thermal ellipsoids at the 30% prbability level. Hydrogen spheres are drawn with an arbitrary radius.
[Figure 2] Fig. 2. Crystal packing view looking down the a axis, thus showing the two-dimensional-supramolecular structure formed by N—H···O and C—H···π interactions (dashed lines).
5-Methyl-1H-indole-3-carbaldehyde top
Crystal data top
C10H9NOF(000) = 336
Mr = 159.18Dx = 1.267 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 1172 reflections
a = 16.9456 (19) Åθ = 2.4–22.1°
b = 5.7029 (6) ŵ = 0.08 mm1
c = 8.6333 (9) ÅT = 296 K
V = 834.31 (15) Å3Lath, yellow
Z = 40.47 × 0.15 × 0.05 mm
Data collection top
Bruker APEXII CCD
diffractometer
1147 independent reflections
Radiation source: fine-focus sealed tube717 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ϕ and ω scansθmax = 28.8°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2213
Tmin = 0.962, Tmax = 0.996k = 77
5499 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H 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 parametersΔρmax = 0.12 e Å3
1 restraintΔρmin = 0.14 e Å3
Crystal data top
C10H9NOV = 834.31 (15) Å3
Mr = 159.18Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 16.9456 (19) ŵ = 0.08 mm1
b = 5.7029 (6) ÅT = 296 K
c = 8.6333 (9) Å0.47 × 0.15 × 0.05 mm
Data collection top
Bruker APEXII CCD
diffractometer
1147 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
717 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.996Rint = 0.039
5499 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0381 restraint
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 0.98Δρmax = 0.12 e Å3
1147 reflectionsΔρmin = 0.14 e Å3
113 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
O10.27204 (11)1.0610 (3)0.6573 (2)0.0742 (6)
N10.29282 (16)0.4126 (4)0.3481 (3)0.0760 (7)
H1N0.2766 (15)0.285 (5)0.290 (5)0.091*
C10.2435 (2)0.5303 (4)0.4384 (3)0.0717 (8)
H10.19130.48790.45630.086*
C20.27969 (14)0.7233 (4)0.5018 (3)0.0587 (6)
C30.35916 (14)0.7227 (4)0.4414 (3)0.0535 (6)
C40.42432 (15)0.8710 (4)0.4561 (3)0.0554 (6)
H40.42121.00360.51850.066*
C50.49316 (16)0.8208 (4)0.3782 (3)0.0638 (7)
C60.49673 (18)0.6225 (5)0.2839 (4)0.0785 (8)
H60.54340.59040.23110.094*
C70.4341 (2)0.4736 (5)0.2661 (3)0.0766 (8)
H70.43770.34220.20260.092*
C80.36502 (18)0.5241 (4)0.3453 (3)0.0626 (7)
C90.24192 (16)0.8851 (4)0.6026 (3)0.0640 (6)
H90.18970.85440.62920.077*
C100.56347 (18)0.9773 (6)0.3966 (4)0.0860 (10)
H10A0.56541.08660.31210.129*
H10B0.61070.88420.39690.129*
H10C0.55951.06150.49260.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0843 (15)0.0640 (9)0.0743 (12)0.0106 (9)0.0086 (10)0.0101 (9)
N10.109 (2)0.0565 (10)0.0622 (13)0.0129 (12)0.0146 (15)0.0053 (11)
C10.0820 (19)0.0660 (13)0.0671 (17)0.0143 (15)0.0109 (17)0.0081 (14)
C20.0722 (18)0.0533 (11)0.0508 (12)0.0012 (11)0.0030 (12)0.0033 (10)
C30.0668 (17)0.0499 (10)0.0440 (11)0.0056 (10)0.0070 (11)0.0013 (10)
C40.0639 (16)0.0528 (10)0.0495 (12)0.0026 (11)0.0052 (12)0.0003 (10)
C50.0640 (18)0.0699 (14)0.0575 (14)0.0141 (12)0.0022 (13)0.0073 (13)
C60.081 (2)0.0869 (18)0.0678 (16)0.0295 (15)0.0074 (16)0.0032 (15)
C70.105 (2)0.0657 (14)0.0590 (16)0.0237 (16)0.0008 (17)0.0133 (12)
C80.089 (2)0.0488 (10)0.0502 (13)0.0051 (12)0.0112 (14)0.0021 (11)
C90.0662 (17)0.0683 (13)0.0574 (14)0.0083 (14)0.0013 (13)0.0124 (13)
C100.068 (2)0.102 (2)0.088 (2)0.0008 (17)0.0032 (16)0.0136 (17)
Geometric parameters (Å, º) top
O1—C91.221 (3)C4—H40.9300
N1—C11.326 (4)C5—C61.395 (4)
N1—C81.379 (4)C5—C101.497 (4)
N1—H1N0.93 (3)C6—C71.368 (4)
C1—C21.374 (3)C6—H60.9300
C1—H10.9300C7—C81.385 (4)
C2—C91.421 (3)C7—H70.9300
C2—C31.444 (3)C9—H90.9300
C3—C41.397 (3)C10—H10A0.9600
C3—C81.408 (3)C10—H10B0.9600
C4—C51.377 (3)C10—H10C0.9600
C1—N1—C8109.7 (2)C7—C6—C5122.3 (3)
C1—N1—H1N121.9 (18)C7—C6—H6118.8
C8—N1—H1N128.1 (18)C5—C6—H6118.8
N1—C1—C2111.0 (3)C6—C7—C8118.1 (2)
N1—C1—H1124.5C6—C7—H7121.0
C2—C1—H1124.5C8—C7—H7121.0
C1—C2—C9124.3 (3)N1—C8—C7131.4 (2)
C1—C2—C3105.7 (2)N1—C8—C3107.3 (2)
C9—C2—C3130.0 (2)C7—C8—C3121.2 (3)
C4—C3—C8119.0 (2)O1—C9—C2125.6 (3)
C4—C3—C2134.7 (2)O1—C9—H9117.2
C8—C3—C2106.3 (2)C2—C9—H9117.2
C5—C4—C3120.0 (2)C5—C10—H10A109.5
C5—C4—H4120.0C5—C10—H10B109.5
C3—C4—H4120.0H10A—C10—H10B109.5
C4—C5—C6119.4 (3)C5—C10—H10C109.5
C4—C5—C10119.9 (2)H10A—C10—H10C109.5
C6—C5—C10120.7 (3)H10B—C10—H10C109.5
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the N1/C1/C2/C3/C8 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.93 (3)1.90 (3)2.818 (3)169 (3)
C9—H9···Cgii0.932.913.312 (3)107
Symmetry codes: (i) x+1/2, y1, z1/2; (ii) x+1/2, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC10H9NO
Mr159.18
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)296
a, b, c (Å)16.9456 (19), 5.7029 (6), 8.6333 (9)
V3)834.31 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.47 × 0.15 × 0.05
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.962, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections
5499, 1147, 717
Rint0.039
(sin θ/λ)max1)0.677
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.107, 0.98
No. of reflections1147
No. of parameters113
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the N1/C1/C2/C3/C8 ring.
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.93 (3)1.90 (3)2.818 (3)169 (3)
C9—H9···Cgii0.932.913.312 (3)107
Symmetry codes: (i) x+1/2, y1, z1/2; (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

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationJohnson, 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
First citationNg, S. W. (2007). Acta Cryst. E63, o2732.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

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ISSN: 2056-9890
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