Tris(methylammonium thiocyanurate) monohydrate

Yimin Hou; Yunxia Yang

doi:10.1107/S1600536810050312

. 2010 Dec 8;67(Pt 1):o44. doi: 10.1107/S1600536810050312

Tris(methylammonium thiocyanurate) monohydrate

Yimin Hou ^a, Yunxia Yang ^b,^*

PMCID: PMC3050359 PMID: 21522753

Abstract

In the title compound, 3[(CH₃)₃HN⁺]·3C₃H₂N₃S₃ ⁻·H₂O, two independent trithiocyanurate anions construct a planar hydrogen-bonded ribbon with two N—H⋯S hydrogen bonds linking each pair of adjacent anions in the chain. The third independent anion and the water molecule form a chain by way of N—H⋯S and O—H⋯S contacts, which propagates parallel to the ribbon. The chains and ribbons are cross-linked by O—H⋯S hydrogen bonds, generating sheets. The three independent trimethylammonium cations are contained between the sheets by way of various N—H⋯S and N—H⋯N contacts.

Related literature

For hydrogen-bond formation in the compounds of trithiocyanuric acid, see: Dean et al. (2004 ▶).

Experimental

Crystal data

3C₃H₁₀N⁺·3C₃H₂N₃S₃ ⁻·H₂O
M _r = 727.23
Triclinic,
a = 11.3466 (1) Å
b = 12.6474 (1) Å
c = 12.8135 (1) Å
α = 76.950 (1)°
β = 84.762 (1)°
γ = 82.274 (1)°
V = 1771.51 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 296 K
0.55 × 0.40 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan SADABS (Bruker, 2007 ▶) T _min = 0.735, T _max = 0.948
14356 measured reflections
6243 independent reflections
5406 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.103
S = 1.05
6243 reflections
388 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810050312/hb5752sup1.cif

e-67-00o44-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050312/hb5752Isup2.hkl

e-67-00o44-Isup2.hkl^{(305.6KB, 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
O1W—H1WA⋯S3	0.86	2.57	3.284 (2)	140
O1W—H1WB⋯S9ⁱ	0.87	2.52	3.355 (2)	161
N2—H2⋯S4ⁱⁱ	0.85 (1)	2.48 (1)	3.3196 (17)	168 (2)
N3—H3⋯S6ⁱⁱⁱ	0.85 (1)	2.48 (1)	3.3203 (17)	168 (2)
N4—H4⋯S2ⁱⁱ	0.86 (1)	2.45 (1)	3.2962 (17)	169 (2)
N5—H5⋯S1ⁱⁱⁱ	0.86 (1)	2.49 (1)	3.3316 (17)	167 (2)
N7—H7⋯O1W	0.86 (1)	2.03 (1)	2.878 (3)	172 (3)
N9—H9⋯S8^iv	0.86 (1)	2.63 (1)	3.470 (2)	167 (3)
N10—H10⋯N6	0.87 (1)	1.95 (1)	2.804 (3)	168 (3)
N11—H11⋯N1	0.86 (1)	1.95 (1)	2.795 (2)	164 (3)
N12—H12⋯S7^v	0.85 (1)	2.69 (2)	3.439 (2)	148 (3)

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

Acknowledgments

We thank Northwest Normal University for supporting this study.

supplementary crystallographic information

Comment

Trithiocyanuric acid, which can be regarded as the polymer of three thiourea molecules, have a strong tendency to form various hydrogen bonds (Dean et al. 2004). Here we report the crystal structure of the title ammonium water-trithiocyanurate, 3[(CH₃)₃HN⁺].3C₃H₂N₃S₃^-.H₂O, (I). In this structure, two independent trithiocyanurate anions containing S1 and S4 atoms firstly form the hydrogen-bonded ribbon parallel to (010) plane by four N—H···S hydrogen bonds, and then between two planar ribbons, there exist a totally different waving ribbon composed of the third trithiocyanurate anion and the only water molecule, in which the anion links the water molecule with varied N—H···S and O—H···S contacts (Fig. 2). With the existence of one independent O—H···S interaction between the aforementioned planar hydrogen-bonded ribbon and the waving ribbon, two planar ribbons and one waving ribbon can yield the larger hydrogen-bonded unit as shown in Fig. 3. The ammonium cations, with the existence of N—H···S and N—H···N interactions, are stably accommodated to the intervals of these separated units to form the stable crystal structure.

Experimental

Trithiocyanuric acid (0.044 g, 0.25 mmol) was dissolved in a water-ethanol (1:2 v/v) mixture and a 33% solution of trimethyl amine was added to neutralize the acid. Colorless block crystals separated after several weeks.