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Volume 68 
Part 11 
Page o3072  
November 2012  

Received 28 August 2012
Accepted 1 October 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.100
Data-to-parameter ratio = 18.2
Details
Open access

N-[4-(2-Propyn-1-yloxy)phenyl]acetamide

aResearch Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg, 2006, South Africa
Correspondence e-mail: mullera@uj.ac.za

The title compound, C11H11NO2, was synthesized by chemoselective N-acetylation of 4-aminophenol followed by reaction with propargyl bromide in the presence of K2CO3. the acetamide and propyn-1-yloxy substituents form dihedral angles of 18.31 (6) and 7.01 (10)°, respectively, with the benzene ring. In the crystal, molecules are linked by N-H...O hydrogen bonds into chains along [010]. C-H...O and C-H...[pi] interactions also occur.

Related literature

For background to the development of hybrid drug candidates against tuberculosis, malaria and cancer, see: Morphy et al. (2004[Morphy, R., Kay, C. & Rankovic, Z. (2004). Drug Discov. Today, 9, 641-651.]). For details of the synthesis of the title compound, see: Hoogendoorn et al. (2011[Hoogendoorn, S., Blom, A. E. M., Willems, L. I., van der Marel, G. A. & Overkleeft, H. S. (2011). Org. Lett. 13, 5656-5659.]); Reppe (1955[Reppe, W. (1955). Justus Liebigs Ann. Chem. 596, 38-79.]).

[Scheme 1]

Experimental

Crystal data
  • C11H11NO2

  • Mr = 189.21

  • Monoclinic, P 21 /c

  • a = 13.973 (2) Å

  • b = 9.1794 (13) Å

  • c = 7.5105 (11) Å

  • [beta] = 99.441 (4)°

  • V = 950.3 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.3 × 0.26 × 0.23 mm

Data collection
  • Bruker APEX DUO 4K CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.969, Tmax = 0.981

  • 6753 measured reflections

  • 2388 independent reflections

  • 2103 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.100

  • S = 1.04

  • 2388 reflections

  • 131 parameters

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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4-C11 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.879 (14) 1.993 (14) 2.8695 (11) 175.2 (13)
C9-H9B...O2i 0.98 2.53 3.4043 (14) 148
C5-H5...Cg1ii 0.95 2.69 3.5171 (12) 146
C9-H9A...Cg1iii 0.98 2.94 3.7373 (12) 139
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]; (ii) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) -x, -y, -z.

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2008[Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2291 ).


Acknowledgements

Research funds of the University of Johannesburg and the Research Centre for Synthesis and Catalysis are gratefully acknowledged. Mrs Z. H. Phasha is thanked for the data collection.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Hoogendoorn, S., Blom, A. E. M., Willems, L. I., van der Marel, G. A. & Overkleeft, H. S. (2011). Org. Lett. 13, 5656-5659.  [ISI] [CrossRef] [ChemPort] [PubMed]
Morphy, R., Kay, C. & Rankovic, Z. (2004). Drug Discov. Today, 9, 641-651.  [ISI] [CrossRef] [PubMed] [ChemPort]
Reppe, W. (1955). Justus Liebigs Ann. Chem. 596, 38-79.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3072  [ doi:10.1107/S1600536812041207 ]

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