4-Ethoxy­imino-N′-methoxy­pyrrolidin-1-ium-3-carboximidamidium dichloride

Guo, Q.; Sun, L.; Guo, H.; Liu, M.

doi:10.1107/S1600536809004772

Volume 65
Part 3
Page o580
March 2009

Received 11 January 2009
Accepted 10 February 2009
Online 21 February 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R = 0.077
wR = 0.210
Data-to-parameter ratio = 15.3
Details

4-Ethoxyimino-N'-methoxypyrrolidin-1-ium-3-carboximidamidium dichloride

Qiang Guo,^a Lanying Sun,^a Huiyuan Guo ^a and Mingliang Liu ^a ^*

^aInstitute of Medicinal Biotechnology, Chinese Academy of Medical Sciences, and Peking Union Medical College, Beijing 100050, People's Republic of China
Correspondence e-mail: lmllyx@yahoo.com.cn

The title compound, C₈H₁₈N₄O₂²⁺·2Cl^-, contains two oxime groups. The methyl oxime group has a Z configuration, and the ethyl oxime group is disordered, with both Z and E configurations in occupancies of 0.840 (8) and 0.160 (8), respectively. In the crystal structure, there are a number of N-HCl hydrogen bonds.

Related literature

For properties of quinolone derivatives, see: Ball et al. (1998); Ray et al. (2005). For the synthesis of new quinolones, see: Anderson & Osheroff (2001); Choi et al. (2004); Wang, Guo et al. (2008). For some crystal structures of quinolones, see: Wang, Liu et al. (2008).

Experimental

Crystal data

C₈H₁₈N₄O₂²⁺·2Cl^-
M_r = 273.16
Orthorhombic, P b c n
a = 12.7355 (14) Å
b = 8.8506 (12) Å
c = 26.334 (2) Å
V = 2968.3 (6) Å³
Z = 8
Mo K radiation
= 0.43 mm^-1
T = 298 K
0.23 × 0.20 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.907, T_max = 0.922
14370 measured reflections
2597 independent reflections
1986 reflections with I > 2(I)
R_int = 0.062

Refinement

R[F² > 2(F²)] = 0.077
wR(F²) = 0.210
S = 1.08
2597 reflections
170 parameters
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3BCl1	0.86	2.29	3.144 (4)	173
N3-H3ACl1ⁱ	0.86	2.41	3.213 (4)	156
N2-H2Cl2ⁱⁱ	0.86	2.21	3.029 (4)	160
N1-H1BCl2	0.90	2.18	3.035 (4)	159
N1-H1ACl1ⁱⁱⁱ	0.90	2.20	3.076 (4)	165
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT and SHELXTL (Sheldrick, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); 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: PK2146 ).

Acknowledgements

This work was supported by the IMB Research Foundation.

References

Anderson, V. E. & Osheroff, N. (2001). Curr. Pharm. Des. 7, 337-353.
Ball, P., Tilloston, G. & Fernald, A. (1998). Expert Opin. Investig. Drugs, 7, 761-783.
Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, D. R., Shin, J. H. & Yang, J. (2004). Bioorg. Med. Chem. Lett. 14, 1273-1277.
Ray, S., Pathak, S. R. & Chaturvedi, D. (2005). Drugs Future, 30, 161-180.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, X. Y., Guo, Q. & Wang, Y. C. (2008). Acta Pharmacol. Sin. 43, 819-827.
Wang, J., Liu, M., Cao, J. & Wang, Y. (2008). Acta Cryst. E64, o2294.

organic compounds