PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2200.
Published online 2008 October 25. doi:  10.1107/S1600536808034156
PMCID: PMC2959652

Ethyl 1,3-dimethyl-1H-indole-2-carboxyl­ate

Abstract

In the title compound, C13H15NO2, the plane of the indole ring forms a dihedral angle of 5.26 (6)° with the ester group and the ethyl side-chain C atoms. The crystal packing is stabilized by weak inter­molecular C—H(...)O and C—H(...)π inter­actions.

Related literature

For biological activities of indole derivatives, see: Okabe & Adachi (1998 [triangle]); Schollmeyer et al. (1995 [triangle]). For related structures, see: Chakkaravarthi et al. (2007 [triangle], 2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2200-scheme1.jpg

Experimental

Crystal data

  • C13H15NO2
  • M r = 217.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2200-efi1.jpg
  • a = 7.5511 (3) Å
  • b = 12.2476 (6) Å
  • c = 12.9449 (5) Å
  • β = 105.488 (2)°
  • V = 1153.71 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 295 (2) K
  • 0.25 × 0.20 × 0.20 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.979, T max = 0.983
  • 15440 measured reflections
  • 3620 independent reflections
  • 2068 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.184
  • S = 1.03
  • 3620 reflections
  • 148 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034156/bq2100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034156/bq2100Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Madras, for the data collection.

supplementary crystallographic information

Comment

The indole derivatives are found to possess antibacterial (Okabe and Adachi, 1998) and antitumour activities (Schollmeyer et al., 1995). In continuation to our studies in indole derivatives, we determine the crystal structure of the title compound (I). The geometric parameters of the molecule of (I) (Fig. 1) agree well with the reported structures (Chakkaravarthi et al., 2007; Chakkaravarthi et al., 2008).

The five- (N1/C1/C6/C7/C8) and six- (C1—C6) membered rings in the indane group are almost planar, with a dihedral angle of 1.67 (6)° between these rings. The plane of indole ring forms a dihedral angle of 5.26 (6)° with the ester group. The molecular packing is stabilized by weak intramolecular C—H···O interaction and the crystal packing of (I) is stabilized by weak intermolecular C—H···O and C—H···π interactions (Table 1) (Fig. 2).

Experimental

To a stirred suspension of NaH (0.6 mmol, hexane washed) in THF (2 ml), a solution of 2-carbethoxy-3-methyl indole (0.5 mmol) in THF (2 ml) was added and stirred for 30 minutes at room temperature. To the reaction mixture, a solution of Iodomethane (0.6 mmol) was added and stirring was continued for further 6 hr. After the indole was consumed (monitored by TLC), the reaction mixture was quenched with cold dil HCl (25 ml), extracted with ethyl acetate (2 x 10 ml) and dried (Na2SO4). Removal of solvent followed by crystalization (hexane) afforded as yellow crystal.

Refinement

H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic H atoms, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2 and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms.

Figures

Fig. 1.
The molecular structure of (I), with atom labeling scheme. Displacement ellipsoids are drawn at 50% probability level.
Fig. 2.
The crystal structure of (I), viewed down the a face. For the sake of clarity, H atoms not involved in interaction have been omitted.

Crystal data

C13H15NO2F(000) = 464
Mr = 217.26Dx = 1.251 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4312 reflections
a = 7.5511 (3) Åθ = 2.3–24.1°
b = 12.2476 (6) ŵ = 0.08 mm1
c = 12.9449 (5) ÅT = 295 K
β = 105.488 (2)°Block, yellow
V = 1153.71 (9) Å30.25 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker Kappa APEXII diffractometer3620 independent reflections
Radiation source: fine-focus sealed tube2068 reflections with I > 2σ(I)
graphiteRint = 0.026
ω and [var phi] scansθmax = 31.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.979, Tmax = 0.983k = −17→17
15440 measured reflectionsl = −18→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0844P)2 + 0.1542P] where P = (Fo2 + 2Fc2)/3
3620 reflections(Δ/σ)max < 0.001
148 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = −0.17 e Å3

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

xyzUiso*/Ueq
C10.7616 (2)−0.19859 (13)0.57067 (13)0.0527 (4)
C20.7747 (2)−0.30504 (16)0.61130 (15)0.0653 (5)
H20.8324−0.31940.68290.078*
C30.7003 (3)−0.38637 (16)0.54252 (18)0.0750 (5)
H30.7075−0.45770.56790.090*
C40.6132 (3)−0.36648 (16)0.43493 (18)0.0738 (5)
H40.5646−0.42460.39010.089*
C50.5983 (2)−0.26368 (16)0.39465 (14)0.0655 (4)
H50.5386−0.25100.32300.079*
C60.67448 (19)−0.17669 (13)0.46276 (12)0.0525 (4)
C70.68784 (19)−0.06336 (13)0.44615 (11)0.0501 (4)
C80.78272 (19)−0.01966 (13)0.54312 (11)0.0512 (4)
C90.9305 (3)−0.09425 (17)0.73226 (14)0.0757 (5)
H9A0.9384−0.16510.76500.114*
H9B0.8689−0.04490.76870.114*
H9C1.0519−0.06750.73710.114*
C100.6076 (2)−0.00822 (15)0.34166 (13)0.0670 (5)
H10A0.54640.05750.35340.100*
H10B0.5209−0.05610.29550.100*
H10C0.70380.00950.30880.100*
C110.8333 (2)0.09395 (14)0.57069 (13)0.0559 (4)
C120.8335 (2)0.27250 (13)0.50367 (14)0.0644 (4)
H12A0.96520.28370.52860.077*
H12B0.77710.30070.55730.077*
C130.7583 (3)0.32875 (18)0.40024 (17)0.0805 (6)
H13A0.80790.29620.34650.121*
H13B0.79130.40460.40770.121*
H13C0.62690.32190.37930.121*
N10.82742 (18)−0.10221 (11)0.61980 (10)0.0568 (4)
O10.9033 (2)0.12730 (12)0.65918 (10)0.0943 (5)
O20.79272 (16)0.15785 (9)0.48555 (9)0.0632 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0489 (7)0.0561 (9)0.0535 (9)0.0029 (6)0.0146 (6)0.0022 (7)
C20.0636 (9)0.0662 (11)0.0666 (11)0.0026 (8)0.0182 (8)0.0136 (9)
C30.0774 (12)0.0564 (11)0.0939 (15)−0.0017 (9)0.0278 (11)0.0091 (10)
C40.0742 (11)0.0606 (11)0.0849 (14)−0.0079 (9)0.0183 (10)−0.0079 (10)
C50.0627 (9)0.0696 (11)0.0595 (10)−0.0025 (8)0.0081 (7)−0.0072 (9)
C60.0476 (7)0.0574 (9)0.0519 (8)0.0043 (6)0.0122 (6)0.0002 (7)
C70.0499 (7)0.0552 (9)0.0439 (8)0.0047 (6)0.0104 (6)−0.0002 (6)
C80.0529 (8)0.0556 (9)0.0459 (8)0.0041 (6)0.0144 (6)0.0012 (7)
C90.0883 (13)0.0815 (13)0.0488 (9)0.0011 (10)0.0035 (9)0.0088 (9)
C100.0770 (11)0.0675 (11)0.0492 (9)0.0038 (9)0.0043 (8)0.0050 (8)
C110.0624 (9)0.0597 (10)0.0462 (8)0.0004 (7)0.0155 (7)−0.0025 (7)
C120.0722 (10)0.0549 (10)0.0682 (11)0.0016 (8)0.0226 (8)−0.0044 (8)
C130.0902 (13)0.0688 (12)0.0804 (13)0.0093 (10)0.0189 (11)0.0097 (10)
N10.0588 (7)0.0631 (9)0.0467 (7)0.0022 (6)0.0109 (6)0.0036 (6)
O10.1481 (14)0.0728 (9)0.0498 (7)−0.0162 (9)0.0050 (8)−0.0092 (6)
O20.0805 (8)0.0518 (7)0.0536 (7)−0.0007 (5)0.0113 (6)−0.0014 (5)

Geometric parameters (Å, °)

C1—N11.370 (2)C9—N11.459 (2)
C1—C21.400 (2)C9—H9A0.9600
C1—C61.402 (2)C9—H9B0.9600
C2—C31.354 (3)C9—H9C0.9600
C2—H20.9300C10—H10A0.9600
C3—C41.394 (3)C10—H10B0.9600
C3—H30.9300C10—H10C0.9600
C4—C51.356 (3)C11—O11.198 (2)
C4—H40.9300C11—O21.319 (2)
C5—C61.404 (2)C12—O21.443 (2)
C5—H50.9300C12—C131.478 (3)
C6—C71.412 (2)C12—H12A0.9700
C7—C81.377 (2)C12—H12B0.9700
C7—C101.488 (2)C13—H13A0.9600
C8—N11.394 (2)C13—H13B0.9600
C8—C111.462 (2)C13—H13C0.9600
N1—C1—C2130.38 (16)H9A—C9—H9C109.5
N1—C1—C6108.26 (14)H9B—C9—H9C109.5
C2—C1—C6121.33 (16)C7—C10—H10A109.5
C3—C2—C1117.57 (17)C7—C10—H10B109.5
C3—C2—H2121.2H10A—C10—H10B109.5
C1—C2—H2121.2C7—C10—H10C109.5
C2—C3—C4122.06 (18)H10A—C10—H10C109.5
C2—C3—H3119.0H10B—C10—H10C109.5
C4—C3—H3119.0O1—C11—O2122.77 (16)
C5—C4—C3121.00 (18)O1—C11—C8125.30 (16)
C5—C4—H4119.5O2—C11—C8111.93 (14)
C3—C4—H4119.5O2—C12—C13107.02 (15)
C4—C5—C6119.02 (17)O2—C12—H12A110.3
C4—C5—H5120.5C13—C12—H12A110.3
C6—C5—H5120.5O2—C12—H12B110.3
C1—C6—C5119.01 (15)C13—C12—H12B110.3
C1—C6—C7107.83 (14)H12A—C12—H12B108.6
C5—C6—C7133.16 (15)C12—C13—H13A109.5
C8—C7—C6106.51 (13)C12—C13—H13B109.5
C8—C7—C10129.70 (16)H13A—C13—H13B109.5
C6—C7—C10123.78 (14)C12—C13—H13C109.5
C7—C8—N1109.60 (14)H13A—C13—H13C109.5
C7—C8—C11129.14 (14)H13B—C13—H13C109.5
N1—C8—C11121.25 (14)C1—N1—C8107.79 (13)
N1—C9—H9A109.5C1—N1—C9123.47 (14)
N1—C9—H9B109.5C8—N1—C9128.70 (15)
H9A—C9—H9B109.5C11—O2—C12116.72 (13)
N1—C9—H9C109.5
N1—C1—C2—C3−177.99 (16)C6—C7—C8—C11−179.58 (14)
C6—C1—C2—C30.1 (2)C10—C7—C8—C11−0.7 (3)
C1—C2—C3—C40.0 (3)C7—C8—C11—O1173.58 (17)
C2—C3—C4—C5−0.5 (3)N1—C8—C11—O1−5.4 (3)
C3—C4—C5—C60.9 (3)C7—C8—C11—O2−6.4 (2)
N1—C1—C6—C5178.77 (13)N1—C8—C11—O2174.65 (12)
C2—C1—C6—C50.3 (2)C2—C1—N1—C8178.04 (15)
N1—C1—C6—C7−0.08 (16)C6—C1—N1—C8−0.24 (16)
C2—C1—C6—C7−178.54 (14)C2—C1—N1—C9−0.1 (3)
C4—C5—C6—C1−0.8 (2)C6—C1—N1—C9−178.40 (14)
C4—C5—C6—C7177.72 (16)C7—C8—N1—C10.48 (16)
C1—C6—C7—C80.37 (16)C11—C8—N1—C1179.62 (13)
C5—C6—C7—C8−178.25 (16)C7—C8—N1—C9178.52 (15)
C1—C6—C7—C10−178.61 (14)C11—C8—N1—C9−2.3 (2)
C5—C6—C7—C102.8 (3)O1—C11—O2—C12−1.2 (2)
C6—C7—C8—N1−0.52 (15)C8—C11—O2—C12178.80 (13)
C10—C7—C8—N1178.38 (15)C13—C12—O2—C11−173.84 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C10—H10A···O20.962.492.858 (2)103
C2—H2···O1i0.932.533.401 (2)156
C12—H12A···Cg1ii0.972.763.646 (2)152

Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+2, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2100).

References

  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3673.
  • Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542. [PMC free article] [PubMed]
  • Okabe, N. & Adachi, Y. (1998). Acta Cryst. C54, 386–387.
  • Schollmeyer, D., Fischer, G. & Pindur, U. (1995). Acta Cryst. C51, 2572–2575.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography