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Volume 69 
Part 8 
Page o1207  
August 2013  

Received 27 June 2013
Accepted 29 June 2013
Online 6 July 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.083
Data-to-parameter ratio = 10.6
Details
Open access

Napropamide

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
Correspondence e-mail: jekim@gnu.ac.kr, thkim@gnu.ac.kr

The title compound [systematic name: N,N-diethyl-2-(naphthalen-1-yloxy)propanamide], C17H21NO2, crystallizes with two independent molecules in the asymmetric unit in which the dihedral angles between the naphthalene ring systems and the amide groups are 88.1 (9) and 88.7 (3)°. Four C-H...O hydrogen bonds stabilize the crystal structure.

Related literature

For the herbicidal effects of the title compound, see: Freeman (1986[Freeman, J. A. (1986). Can. J. Plant Sci. 66, 141-152.]). For information on the synthesis of the title compound, see: Gless (1986[Gless, R. D. Jr (1986). Synth. Commun. 16, 633-638.]). For a related crystal structure, see: Au-Yeung et al. (2009[Au-Yeung, H. Y., Pengo, P., Pantos, G. D., Otto, S. & Sanders, J. K. (2009). Chem. Commun. pp. 419-421.]).

[Scheme 1]

Experimental

Crystal data
  • C17H21NO2

  • Mr = 271.35

  • Monoclinic, P 21

  • a = 9.8733 (3) Å

  • b = 10.7710 (4) Å

  • c = 14.1044 (5) Å

  • [beta] = 97.943 (2)°

  • V = 1485.55 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 173 K

  • 0.35 × 0.18 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.988

  • 26573 measured reflections

  • 3897 independent reflections

  • 3297 reflections with I > 2[sigma](I)

  • Rint = 0.041

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

  • wR(F2) = 0.083

  • S = 1.03

  • 3897 reflections

  • 367 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C25-H25...O2 0.95 2.41 3.228 (3) 144
C6-H6...O2i 0.95 2.53 3.388 (3) 150
C7-H7...O4ii 0.95 2.60 3.481 (3) 154
C23-H23...O4iii 0.95 2.46 3.376 (3) 161
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z]; (ii) [-x+1, y-{\script{3\over 2}}, -z]; (iii) [-x+1, y-{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5338 ).


Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2012M2B2A4029305).

References

Au-Yeung, H. Y., Pengo, P., Pantos, G. D., Otto, S. & Sanders, J. K. (2009). Chem. Commun. pp. 419-421.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Freeman, J. A. (1986). Can. J. Plant Sci. 66, 141-152.  [CrossRef] [ChemPort]
Gless, R. D. Jr (1986). Synth. Commun. 16, 633-638.  [CrossRef] [ChemPort] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1207  [ doi:10.1107/S1600536813017947 ]

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