Received 24 July 2010
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 - 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.
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).
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 ).
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.
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