4-Nitro­phenol–2,4,6-triamino-1,3,5-triazine–water (2/1/1)

N Kanagathara; G Chakkaravarthi; M K Marchewka; S Gunasekaran; G Anbalagan

doi:10.1107/S1600536812029066

. 2012 Jun 30;68(Pt 7):o2286. doi: 10.1107/S1600536812029066

4-Nitrophenol–2,4,6-triamino-1,3,5-triazine–water (2/1/1)

N Kanagathara ^a, G Chakkaravarthi ^b,^*, M K Marchewka ^c, S Gunasekaran ^d, G Anbalagan ^e,^*

PMCID: PMC3394065 PMID: 22798930

Abstract

In the title adduct, 2C₆H₅NO₃·C₃H₆N₆·H₂O, the melamine and the two independent nitrophenol molecules are essentially planar, with maximum deviations of 0.0294 (10), 0.0706 (12) and 0.0742 (12) Å, respectively. In the crystal, N—H⋯N, O—H⋯N, N—H⋯O and O—H⋯O hydrogen bonds link the components into a three-dimensional network. In addition, weak π–π interactions [centroid–centroid distances = 3.728 (3) and 3.749 (3) Å] are observed.

Related literature

For applications of melamine, see: Cook et al. (2005 ▶); Rima et al. (2008 ▶). For a related structure, see: Cousson et al. (2005 ▶).

Experimental

Crystal data

2C₆H₅NO₃·C₃H₆N₆·H₂O
M _r = 422.37
Triclinic,
a = 7.123 (5) Å
b = 10.577 (4) Å
c = 13.680 (5) Å
α = 68.256 (5)°
β = 88.772 (6)°
γ = 76.604 (5)°
V = 928.9 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 295 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.964, T _max = 0.976
21610 measured reflections
5696 independent reflections
4164 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.122
S = 1.03
5696 reflections
311 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029066/lh5493sup1.cif

e-68-o2286-sup1.cif^{(26.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029066/lh5493Isup2.hkl

e-68-o2286-Isup2.hkl^{(273.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812029066/lh5493Isup3.cml

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
O1—H1⋯O7ⁱ	0.90 (2)	1.76 (2)	2.6600 (18)	172 (2)
O4—H4⋯N5	0.91 (2)	1.87 (2)	2.7217 (16)	157 (2)
O7—H7A⋯N4	0.88 (2)	1.94 (2)	2.8020 (18)	166 (2)
O7—H7B⋯O2^iv	0.84 (2)	2.22 (2)	3.0424 (18)	164 (2)
N6—H6A⋯O6ⁱⁱ	0.860 (18)	2.363 (19)	3.0276 (16)	134 (2)
N6—H6B⋯N3ⁱⁱⁱ	0.845 (18)	2.235 (19)	3.080 (2)	178 (2)
N7—H7C⋯O6^v	0.867 (17)	2.250 (17)	3.056 (2)	155 (2)
N7—H7D⋯O1^v	0.894 (19)	2.049 (19)	2.8996 (17)	159 (2)
N8—H8A⋯O3	0.830 (17)	2.367 (18)	3.158 (2)	159 (2)
N8—H8B⋯O7^iv	0.867 (19)	2.517 (18)	3.1890 (19)	135 (2)

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

Acknowledgments

The authors thank SAIF, IIT Madras, for the data collection.

supplementary crystallographic information

Comment

Melamines are used in the production of melamine foam in polymeric cleaning (Rima et al., 2008) and as a chemical intermediate in plastics manufacturing (Cook et al., 2005). Here, we report the crystal structure of a the title compound. The asymmetric unit contains one melamine molecule, two independent nitrophenol molecules and one solvent water molecule.

The geometric parameters of the melamine molecule (I) (Fig. 1) are comparable with those determined by Cousson et al. (2005). The melamine and nitrophenol molecules are essentially planar, with a maximum deviation of -0.0294 (10) Å for atom N4 in the least square plane (N6/C13/C14/N7/N4/C15/N8/N5), -0.0706 (12) Å for atom O2 in the least square plane (O1/C1-C6/N1/O2/O3) and 0.0742 (12) Å for atom O5 in the least square plane (O4/C10/C11/C12/C7/C8/C9/N2/O5/O6).

In the crystal, O—H···N, N—H···O and O—H···O hydrogen bonds (Table 1 & Fig. 2) and π–π interactions [Cg1···Cg1 (1-x,-y,1-z) distance of 3.749 (3)Å; Cg1···Cg2 (x,-1+y,z) distance of 3.728 (3)Å and Cg2···Cg1 (x,1+y,z) distance of 3.728 (3)Å; Cg1 and Cg2 are the centroids of the rings (C1-C6) and (C7-C12), respectively] connect the components of the structure into a three-dimensional network.

Experimental

Melamine (1.2612g, 0.01 mmol) was dissolved in 200 ml of hot solution of distilled water. p-Nitrophenol (1.3911g, 0.01 mmol) was dissolved in 100 ml of distilled water separately. To the hot solution of melamine, p-nitrophenol solution was added gently, and stirred well for nearly five hours to get the homogenous solution and the mixture is allowed to evaporate. Within a few days tiny, transparent, yellowish crystals were formed. Recrystallization was carried out by using distilled water to get the pure crystal suitable for X-ray diffraction.