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Volume 69 
Part 8 
Page o1242  
August 2013  

Received 1 July 2013
Accepted 4 July 2013
Online 13 July 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.117
Data-to-parameter ratio = 19.8
Details
Open access

Ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,bChemistry Department, Faculty of Science, Mini University, 61519 El-Minia, Egypt,cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA,dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

In the title compound, C14H17NO3, the nine-membered 1H-indole ring system is essentially planar [maximum deviation = 0.019 (1) Å]. In the crystal, molecules are linked via N-H...O hydrogen bonds, forming chains along [001]. These chains are linked via C-H...O hydrogen bonds and C-H...[pi] interactions, forming a two-dimensional network lying parallel to the ac plane.

Related literature

For medicinal applications of the drug indomethacin (systematic name: 2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid), see: Paneth (1995[Paneth, N. S. (1995). Future Child, 5, 19-34.]); McIntyre et al. (2001[McIntyre, J., van Overmeire, B. & van den Anker, J. N. (2001). Paediatr. Perinat. Drug Ther. 4, 85-91.]); Abou-Ghannam et al. (2012[Abou-Ghannam, G. M. D., Ihab, M., Usta, M. D., Anwar, H. & Nassar, M. D. (2012). Am. J. Perinatol. 29, 175-186.]). For the synthesis and reactions of indomethacin with other non-steroidal anti-inflammatory molecules, see: Mohamed et al. (2012[Mohamed, S. K., Albayati, M. R., Omara, W. A. M., Abdelhamid, A. A., Potgeiter, H., Hameed, A. S. & Al-Janabi, K. M. (2012). J. Chem. Pharm. Res. 4, 3505-3517.]).

[Scheme 1]

Experimental

Crystal data
  • C14H17NO3

  • Mr = 247.29

  • Monoclinic, P 21 /c

  • a = 7.8117 (5) Å

  • b = 17.1953 (12) Å

  • c = 9.9003 (7) Å

  • [beta] = 106.756 (1)°

  • V = 1273.39 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 150 K

  • 0.23 × 0.21 × 0.06 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.84, Tmax = 1.00

  • 22947 measured reflections

  • 3374 independent reflections

  • 2889 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.117

  • S = 1.08

  • 3374 reflections

  • 170 parameters

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

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.914 (18) 2.013 (18) 2.8987 (14) 162.7 (16)
C7-H7B...O2ii 0.98 2.57 3.4271 (18) 146
C13-H13A...O1iii 0.99 2.55 3.4236 (16) 148
C7-H7A...Cg1iv 0.98 2.99 3.9550 (16) 169
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2618 ).


Acknowledgements

Manchester Metropolitan University, Tulane University and Erciyes University are gratefully acknowledged for supporting this study.

References

Abou-Ghannam, G. M. D., Ihab, M., Usta, M. D., Anwar, H. & Nassar, M. D. (2012). Am. J. Perinatol. 29, 175-186.  [Web of Science] [PubMed]
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
McIntyre, J., van Overmeire, B. & van den Anker, J. N. (2001). Paediatr. Perinat. Drug Ther. 4, 85-91.  [ChemPort]
Mohamed, S. K., Albayati, M. R., Omara, W. A. M., Abdelhamid, A. A., Potgeiter, H., Hameed, A. S. & Al-Janabi, K. M. (2012). J. Chem. Pharm. Res. 4, 3505-3517.  [ChemPort]
Paneth, N. S. (1995). Future Child, 5, 19-34.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1242  [ doi:10.1107/S1600536813018618 ]

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