2,4-Diamino-6-methyl-1,3,5-triazine ethanol solvate

Zun-Hong Xiao

doi:10.1107/S1600536808000159

. 2008 Jan 9;64(Pt 2):o411. doi: 10.1107/S1600536808000159

2,4-Diamino-6-methyl-1,3,5-triazine ethanol solvate

Zun-Hong Xiao ^a,^*

PMCID: PMC2960281 PMID: 21201439

Abstract

The crystal structure of the title compound, C₄H₇N₅·C₂H₆O, is determined by extensive hydrogen bonding. A sequence of dimeric associations, formed by N—H(amino)⋯N(ring), connects the triazine rings into a molecular tape. Molecules are linked into a supramolecular structure by N—H⋯O and O—H⋯O hydrogen bonds. The asymmetric unit consists of two formula units.

Related literature

For general background, see: Sebenik et al. (1989 ▶); Tashiro & Oiwa (1981 ▶).

Experimental

Crystal data

C₄H₇N₅·C₂H₆O
M _r = 171.21
Triclinic,
a = 8.3860 (6) Å
b = 9.1514 (6) Å
c = 11.9104 (9) Å
α = 88.703 (1)°
β = 87.614 (2)°
γ = 76.668 (2)°
V = 888.56 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 273 (2) K
0.34 × 0.26 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.975, T _max = 0.985
7627 measured reflections
3111 independent reflections
2619 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.118
S = 1.07
3111 reflections
223 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000159/bq2061sup1.cif

e-64-0o411-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000159/bq2061Isup2.hkl

e-64-0o411-Isup2.hkl^{(147KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯N7ⁱ	0.86	2.11	2.9666 (18)	171
N5—H5D⋯N8ⁱⁱ	0.86	2.19	3.0132 (19)	159
N5—H5E⋯O2ⁱⁱⁱ	0.86	2.29	3.0071 (19)	142
N10—H10A⋯O2^iv	0.86	2.10	2.9337 (18)	163
O2—H2⋯O1^v	0.82	1.90	2.7185 (18)	174

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

This work was supported by the Nomarch Education Foundation of Guizhou, China (No. 2004–07).

supplementary crystallographic information

Comment

Triazine compounds are used in pharmaceutical industry as coupling agents for the synthesis of peptides and as side chain of antibiotics, as well as in formulating bactericides and fungicides. 2,4-Diamino-6-methyl-1,3,5-triazine (acetoguanamine) is used as an intermediate for pharmaceuticals and as a modifier and flexibilizer of formaldehyde resins (Sebenik et al., 1989, Tashiro et al., 1981).

The crystal structure of the title compound (Fig. 1) consists of triazine and solvate ethanol molecule. The amino groups are coplanar with the ring plane, the dihedral angle between the triazine ring (C2,N2,C4,N1,C3,N3) and the ring (C8,N7,C9,N8,C10,N6) is 12.73 (7)°. A lot of hydrogen bonds are observed (Table 1), each NH₂ group acts as a donor in hydrogen bond with the ring nitrogen atoms of neighboring molecules, these contacts and the cross-linking interactions stabilize the crystal packing.

Experimental

2,4-diamino-6-methyl-1,3,5-triazine (0.625 g, 0.05 mol) was added to a stirred solvent of ethanol (100 ml) at 50°C for 3 h. After cooling to room temperature, the mixture was filtered. The filtrate was set aside for one week to obtain colorless crystals.