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

Belay, Y.H.; Kinfe, H.H.; Muller, A.

doi:10.1107/S1600536812041207

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 (C-C) = 0.002 Å
R = 0.037
wR = 0.100
Data-to-parameter ratio = 18.2
Details

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

Yonas H. Belay,^a Henok H. Kinfe ^a and Alfred Muller ^a ^*

^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-HO hydrogen bonds into chains along [010]. C-HO 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). For details of the synthesis of the title compound, see: Hoogendoorn et al. (2011); Reppe (1955).

Experimental

Crystal data

C₁₁H₁₁NO₂
M_r = 189.21
Monoclinic, P 2₁ /c
a = 13.973 (2) Å
b = 9.1794 (13) Å
c = 7.5105 (11) Å
= 99.441 (4)°
V = 950.3 (2) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.969, T_max = 0.981
6753 measured reflections
2388 independent reflections
2103 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(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
_max = 0.28 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4-C11 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1O2ⁱ	0.879 (14)	1.993 (14)	2.8695 (11)	175.2 (13)
C9-H9BO2ⁱ	0.98	2.53	3.4043 (14)	148
C5-H5Cg1ⁱⁱ	0.95	2.69	3.5171 (12)	146
C9-H9ACg1ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

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.
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.
Hoogendoorn, S., Blom, A. E. M., Willems, L. I., van der Marel, G. A. & Overkleeft, H. S. (2011). Org. Lett. 13, 5656-5659.
Morphy, R., Kay, C. & Rankovic, Z. (2004). Drug Discov. Today, 9, 641-651.
Reppe, W. (1955). Justus Liebigs Ann. Chem. 596, 38-79.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds