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Volume 69 
Part 7 
Page o1015  
July 2013  

Received 10 April 2013
Accepted 24 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
R = 0.071
wR = 0.217
Data-to-parameter ratio = 13.5
Details
Open access

1-[(6-Chloropyridin-3-yl)methyl]-10-nitro-1,2,3,5,6,7,8,9-octahydro-5,9-methanoimidazo[1,2-a]azocin-5-ol

aShandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, People's Republic of China
Correspondence e-mail: chm_tianzz@ujn.edu.cn

In the title compound, C16H19ClN4O3, the cyclohexane ring displays a chair formation and the tetrahydropyridine ring displays an envelope conformation with the methylene C atom as the flap; the imidazolidine ring also displays an envelope conformation with a methylene C atom as the flap. In the crystal, O-H...N hydrogen bonds between hydroxy groups and pyridine rings link inversion-related molecules into dimers. Weak C-H...O hydrogen bonds further link the dimers into supramolecular chains running along the c axis.

Related literature

For background to the title compound, see: Jeschkel & Nauen (2008[Jeschkel, P. & Nauen, R. (2008). Pest Manage. Sci. 64, 1084-1098.]). For the synthesis, see: Tian et al. (2007[Tian, Z.-Z., Shao, X.-S., Li, Z., Qian, X.-H. & Huang, Q.-C. (2007). J. Agric. Food Chem. 55, 2288-2292.]).

[Scheme 1]

Experimental

Crystal data
  • C16H19ClN4O3

  • Mr = 350.80

  • Monoclinic, P 21 /c

  • a = 13.3975 (14) Å

  • b = 18.7124 (18) Å

  • c = 6.5721 (8) Å

  • [beta] = 97.897 (10)°

  • V = 1632.0 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 296 K

  • 0.38 × 0.24 × 0.23 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.93, Tmax = 0.94

  • 7705 measured reflections

  • 2921 independent reflections

  • 1727 reflections with I > 2[sigma](I)

  • Rint = 0.056

Refinement
  • R[F2 > 2[sigma](F2)] = 0.071

  • wR(F2) = 0.217

  • S = 1.05

  • 2921 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...N4i 0.82 2.04 2.855 (4) 174
C11-H11A...O1ii 0.97 2.53 3.467 (5) 161
C13-H13...O2ii 0.93 2.48 3.265 (5) 142
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x, y, z-1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. 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: XU5695 ).


Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 20902037), the Promotive Research Fund for Excellent Young and Middle-aged Scientists of Shandong Province (grant No. BS2010NY001), and the Opening Fund of Shanghai Key Laboratory of Chemical Biology (grant No. SKLCB-2008-08).

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Jeschkel, P. & Nauen, R. (2008). Pest Manage. Sci. 64, 1084-1098.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Tian, Z.-Z., Shao, X.-S., Li, Z., Qian, X.-H. & Huang, Q.-C. (2007). J. Agric. Food Chem. 55, 2288-2292.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1015  [ doi:10.1107/S1600536813014402 ]

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