N-Ethyl-6-ethyl­amino-4-oxo-1,3,5-triazin-2-aminium chloride (Oxysimazine·HCl)

Brown, J.E.; Baughman, R.G.

doi:10.1107/S1600536810033775

Volume 66
Part 10
Page o2481
October 2010

Received 24 July 2010
Accepted 20 August 2010
Online 4 September 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
R = 0.037
wR = 0.094
Data-to-parameter ratio = 14.9
Details

N-Ethyl-6-ethylamino-4-oxo-1,3,5-triazin-2-aminium chloride (Oxysimazine·HCl)

J. Emery Brown ^a and Russell G. Baughman ^a ^*

^aDepartment of Chemistry, Truman State University, Kirksville, MO 63501-4221, USA
Correspondence e-mail: baughman@truman.edu

In the title molecular salt, C₇H₁₄N₅O⁺·Cl^- (the HCl salt of the oxo derivative of the triazine herbicide simazine), the cation and anion are linked by N-HCl hydrogen bonds. The chloride ion is also involved in a close electrostatic interaction with an inversion-related triazine ring [Clcentroid distance = 3.201 (1) Å]. A [pi] - [pi] interaction having a centroidcentroid distance of 3.456 (2) Å exists between pairs of rings via another inversion relation. The triazine ring and adjacent non-H atoms are essentially planar (r.m.s. deviation = 0.042 Å), while both methyl groups are approximately perpendicular and on the same side of the plane [torsion angles = 79.3 (3) and -84.6 (3)°]. Upon exposure to X-rays for about two days, the color of the title compound changed from colorless to a pale yellow-orange with no apparent affect on the structure as evidenced by no significant change in the intensities of the standard reflections.

Related literature

The structure determinations of twoherbicides have been reported (Black & Baughman, 2010; Baughman & Yu, 1988 and references cited therein) as has information on the mode of action of this class of herbicides (Roberts, 1998). For the Gaussian calculation, see: Frisch et al. (2009).

Experimental

Crystal data

C₇H₁₄N₅O⁺·Cl^-
M_r = 219.68
Orthorhombic, P b c a
a = 8.2804 (5) Å
b = 14.5930 (9) Å
c = 17.9924 (11) Å
V = 2174.1 (2) Å³
Z = 8
Mo K radiation
= 0.33 mm^-1
T = 295 K
0.40 × 0.28 × 0.27 mm

Data collection

Bruker P4 diffractometer
Absorption correction: integration (XSHELL; Bruker, 1999) T_min = 0.912, T_max = 0.927
2548 measured reflections
1969 independent reflections
1316 reflections with I > 2(I)
R_int = 0.026
3 standard reflections every 100 reflections intensity decay: 1.1%

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.094
S = 1.02
1940 reflections
130 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1ACl1	0.86	2.43	3.225 (2)	154
N2-H2ACl1ⁱ	0.86	2.24	3.080 (2)	167
N4-H4CCl1	0.86	2.44	3.246 (2)	156
N5-H5DCl1ⁱ	0.86	2.80	3.536 (2)	144
C5-H5AO1ⁱⁱ	0.96	2.53	3.471 (4)	166
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC and SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2312 ).

Acknowledgements

This material is based upon work supported by the National Science Foundation under grant No. DUE-0431664. The authors thank Eric V. Patterson for the quantum calculations.

References

Baughman, R. G. & Yu, P.-J. (1988). J. Agric. Food Chem. 36, 1294-1296.
Black, H. M. & Baughman, R. G. (2010). Acta Cryst. E66, o2221.
Bruker (1996). XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (1999). XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.
Frisch, M. J., et al. (2009). GAUSSIAN09. Gaussian Inc., Wallingsford, Connecticut, USA.
Roberts, T. R. (1998). Editor. Metabolic Pathways of Agrochemicals, Part 1. Cambridge, England: RSC Publishing.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds