2,4,6-Triamino-1,3,5-triazine-1,3-diium aqua­penta­fluoridoaluminate

Cadiau, A.; Hemon-Ribaud, A.; Leblanc, M.; Maisonneuve, V.

doi:10.1107/S1600536808004091

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Pages m523-m524

doi:10.1107/S1600536808004091

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2,4,6-Triamino-1,3,5-triazine-1,3-diium aquapentafluoridoaluminate

A. Cadiau,^a A. Hemon-Ribaud,^a M. Leblanc ^a and V. Maisonneuve ^a ^*

^aLaboratoire des Oxydes et Fluorures - UMR 6010 CNRS, Faculté des Sciences et Techniques, Université du Maine, Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France
^*Correspondence e-mail: vincent.maisonneuve@univ-lemans.fr

(Received 28 January 2008; accepted 8 February 2008; online 5 March 2008)

The title compound, (C₃H₈N₆)[AlF₅(H₂O)], was obtained by solvothermal synthesis from the reaction of aluminium hydroxide, 1,3,5-triazine-2,4,6-triamine (melamine), aqueous HF and water at 323 K for 48 h. The structure consists of [AlF₅(H₂O)]²⁻ octahedra and diprotonated melaminium cations. Cohesion is ensured by a three-dimensional network of hydrogen bonds.

Related literature

For related literature, see: Adil, Ben Ali et al. (2006 ); Adil, Leblanc & Maisonneuve (2006 ); Farrugia (1999 ); Goreshnik et al. (2002 , 2003 ); Rother et al. (1996 , 1998 ); Schroder et al. (1993 ); Tang et al. (2001 ).

Experimental

Crystal data

(C₃H₈N₆)[AlF₅(H2O)]
M_r = 268.13
Monoclinic, P 2₁ /c
a = 7.571 (2) Å
b = 8.823 (2) Å
c = 13.484 (5) Å
β = 105.53 (3)°
V = 867.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 298 (2) K
0.20 × 0.13 × 0.08 mm

Data collection

Siemens AED2 diffractometer
Absorption correction: none
2500 measured reflections
2500 independent reflections
1441 reflections with I > 2σ(I)
3 standard reflections frequency: 120 min intensity decay: 4%

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.133
S = 1.04
2500 reflections
152 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯N1ⁱ	0.90 (4)	1.94 (5)	2.789 (3)	156 (5)
O1W—H2W⋯F1ⁱⁱ	0.90 (4)	1.63 (4)	2.515 (3)	169 (5)
N2—H2⋯F4ⁱⁱⁱ	0.86	1.75	2.601 (3)	169
N3—H3⋯F2^iv	0.86	2.11	2.871 (3)	148
N3—H3⋯F3^iv	0.86	2.28	2.990 (3)	140
N3—H3⋯F1^iv	0.86	2.52	2.953 (4)	112
N4—H4A⋯F5^v	0.86	2.07	2.763 (3)	138
N4—H4B⋯F2ⁱⁱⁱ	0.86	1.89	2.739 (3)	168
N5—H5A⋯F3	0.86	2.06	2.837 (3)	151
N5—H5B⋯F3^iv	0.86	2.02	2.804 (4)	151
N5—H5B⋯F4	0.86	2.39	2.863 (3)	115
N6—H6A⋯F1^vi	0.86	2.04	2.836 (4)	154
N6—H6B⋯F2^iv	0.86	2.08	2.860 (4)	150
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) -x+1, -y, -z; (vi) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: STADI4 (Stoe & Cie, 1998 ); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1998); 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 ) and DIAMOND (Brandenburg, 2005 ); software used to prepare material for publication: SHELXL97, enCIFer (Version 1.2; Allen et al., 2004 ) and WinGX (Farrugia, 1999).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004091/dn2317sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004091/dn2317Isup2.hkl

checkCIF report

Comment top

Numerous hybrid fluoroaluminates with linear or branched amines are reported; during the last five years more than 20 compounds were evidenced (Goreshnik et al., 2002; Adil, Ben Ali et al., 2006; Adil, Leblanc & Maisonneuve, 2006). At the opposite, only few hybrid fluoroaluminates with cyclic amines are known (Schroder et al., 1993; Rother et al., 1996; Rother et al., 1998; Tang et al., 2001; Goreshnik et al., 2003). 1,3,5-triazine-2,4,6-triamine (melamine) with three primary amines, three tertiary amines and a conjugated planar configuration was selected. (C₃H₈N₆).[AlF₅(H₂O)] is synthesized and constitutes the first melamine templated fluoroaluminate.

The structure is built up from isolated [AlF₅(H₂O)]^2- anions and diprotonated (C₃H₈N₆)²⁺ cations (Fig. 1). A distortion of the aluminium coordination octahedron results from the presence of the water molecule: Al—F distances range from 1.758 (2) to 1.829 (2) Å and Al—O distance is 1.929 (3) Å. Melaminium cations are planar and two tertiary amines are protonated. C, N, H atomic positions are related by a pseudo two fold symmetry axis along the N1—C2—N5 direction. Hydrogen bonded octahedra form infinite inorganic chains along b axis (Fig. 2); the O1W—H2W···F1 hydrogen bonds (2.51 Å) are short. Every melaminium cation is surrounded by five [AlF₅(H₂O)] octahedra (Fig. 3).

Related literature top

For related literature, see: Adil, Ben Ali et al. (2006); Adil, Leblanc & Maisonneuve (2006); Farrugia (1999); Goreshnik et al. (2002, 2003); Rother et al. (1996, 1998); Schroder et al. (1993); Tang et al. (2001).

Experimental top

The title compound was prepared under hydrothermal conditions at 323 K for 48 h using Teflon-lined autoclaves from a started mixture of Al(OH)₃ (Sochal), 1,3,5-triazine-2,4,6-triamine named melamine (Janssen chimica), HF aqueous solution (40%, Prolabo) and deionized water in the molar ratio 1:0.5:8.5:55.5. The resulting crystalline product was washed with water and dried in air. Needle crystals suitable for single-crystal X-ray diffraction were selected using an optical microscope.

Computing details top

Data collection: STADI4 (Stoe & Cie, 1998); cell refinement: STADI4 (Stoe & Cie, 1998); data reduction: X-RED (Stoe & Cie, 1998); 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) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), enCIFer (Version 1.2; Allen et al., 2004) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of the melaminium cation and [AlF₅(H₂O)]^2- anion with the atom-labellin scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. (100) projection of (C₃H₈N₆).[AlF₅(H₂O)] structure.
	Fig. 3. Network of hydrogen bonds between melaminium cations and [AlF₅(H₂O)] octahedra. [Symmetry codes: (iii) 1 - x, y - 1/2, 1/2 - z; (iv) 1 - x, 1/2 + y, 1/2 - z; (v) 1 - x, -y, -z; (vi) 1 + x, 1/2 - y, z - 1/2]

2,4,6-Triamino-1,3,5-triazine-1,3-diium aquapentafluoridoaluminate top

Crystal data top

(C₃H₈N₆)[AlF₅(H2O)]	F(000) = 544
M_r = 268.13	D_x = 2.052 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 30 reflections
a = 7.571 (2) Å	θ = 28–32°
b = 8.823 (2) Å	µ = 0.31 mm⁻¹
c = 13.484 (5) Å	T = 298 K
β = 105.53 (3)°	Parallepiped, colourless
V = 867.8 (5) Å³	0.20 × 0.13 × 0.08 mm
Z = 4

Data collection top

Siemens AED2 diffractometer	R_int = 0.000
Radiation source: fine-focus sealed tube	θ_max = 30.0°, θ_min = 2.8°
Graphite monochromator	h = −10→10
2θ/ω scans	k = 0→12
2500 measured reflections	l = 0→18
2500 independent reflections	3 standard reflections every 120 min
1441 reflections with I > 2σ(I)	intensity decay: 4%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0437P)² + 0.9389P] where P = (F_o² + 2F_c²)/3
2500 reflections	(Δ/σ)_max < 0.001
152 parameters	Δρ_max = 0.46 e Å⁻³
2 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

(C₃H₈N₆)[AlF₅(H2O)]	V = 867.8 (5) Å³
M_r = 268.13	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.571 (2) Å	µ = 0.31 mm⁻¹
b = 8.823 (2) Å	T = 298 K
c = 13.484 (5) Å	0.20 × 0.13 × 0.08 mm
β = 105.53 (3)°

Data collection top

Siemens AED2 diffractometer	R_int = 0.000
2500 measured reflections	3 standard reflections every 120 min
2500 independent reflections	intensity decay: 4%
1441 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.054	2 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.46 e Å⁻³
2500 reflections	Δρ_min = −0.48 e Å⁻³
152 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Al1	0.2088 (1)	0.2232 (1)	0.30136 (7)	0.0163 (2)
F1	0.0457 (3)	0.0750 (2)	0.30467 (16)	0.0288 (5)
F2	0.2911 (3)	0.1978 (2)	0.44074 (14)	0.0251 (4)
F3	0.3778 (3)	0.0880 (2)	0.28702 (17)	0.0299 (5)
F4	0.3610 (3)	0.3839 (2)	0.31272 (16)	0.0267 (5)
F5	0.1237 (3)	0.2429 (2)	0.16732 (14)	0.0304 (5)
O1W	0.0310 (3)	0.3648 (3)	0.32584 (18)	0.0214 (5)
H1W	−0.062 (5)	0.324 (5)	0.346 (4)	0.062 (12)*
H2W	−0.007 (7)	0.444 (4)	0.284 (3)	0.062 (12)*
N1	0.7845 (4)	0.2143 (3)	−0.0619 (2)	0.0202 (6)
N2	0.6746 (4)	0.1144 (3)	0.0739 (2)	0.0195 (6)
H2	0.6499	0.0359	0.1056	0.023*
N3	0.6895 (4)	0.3729 (3)	0.0557 (2)	0.0203 (6)
H3	0.6714	0.4633	0.0748	0.024*
N4	0.7594 (4)	−0.0423 (3)	−0.0409 (2)	0.0232 (6)
H4A	0.7996	−0.0586	−0.0938	0.028*
H4B	0.7310	−0.1173	−0.0074	0.028*
N5	0.5822 (4)	0.2735 (3)	0.1861 (2)	0.0271 (6)
H5A	0.5543	0.1966	0.2181	0.033*
H5B	0.5664	0.3638	0.2063	0.033*
N6	0.8013 (4)	0.4736 (3)	−0.0717 (2)	0.0293 (7)
H6A	0.8446	0.4652	−0.1242	0.035*
H6B	0.7850	0.5619	−0.0486	0.035*
C1	0.7414 (4)	0.0960 (3)	−0.0113 (2)	0.0179 (6)
C2	0.6481 (4)	0.2534 (4)	0.1076 (2)	0.0191 (6)
C3	0.7602 (4)	0.3525 (4)	−0.0271 (2)	0.0199 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Al1	0.0209 (5)	0.0127 (4)	0.0176 (4)	−0.0002 (4)	0.0090 (3)	−0.0014 (4)
F1	0.0359 (13)	0.0199 (10)	0.0351 (11)	−0.0115 (9)	0.0175 (10)	−0.0075 (9)
F2	0.0330 (11)	0.0214 (10)	0.0204 (9)	0.0027 (8)	0.0063 (8)	0.0020 (8)
F3	0.0355 (13)	0.0191 (10)	0.0413 (12)	0.0089 (9)	0.0207 (10)	0.0013 (9)
F4	0.0292 (12)	0.0191 (9)	0.0379 (11)	−0.0069 (8)	0.0197 (10)	−0.0054 (9)
F5	0.0435 (13)	0.0312 (11)	0.0188 (9)	0.0044 (10)	0.0122 (9)	−0.0009 (8)
O1W	0.0240 (13)	0.0179 (11)	0.0251 (12)	0.0055 (10)	0.0113 (10)	0.0066 (9)
N1	0.0263 (14)	0.0171 (13)	0.0202 (13)	−0.0005 (11)	0.0114 (11)	0.0003 (11)
N2	0.0256 (15)	0.0133 (12)	0.0236 (13)	−0.0001 (11)	0.0134 (12)	0.0016 (10)
N3	0.0260 (15)	0.0125 (12)	0.0240 (13)	−0.0006 (10)	0.0097 (12)	−0.0026 (10)
N4	0.0354 (18)	0.0180 (13)	0.0204 (13)	0.0015 (12)	0.0152 (12)	−0.0003 (11)
N5	0.0340 (17)	0.0241 (14)	0.0288 (15)	−0.0016 (13)	0.0181 (13)	−0.0034 (13)
N6	0.0402 (19)	0.0190 (14)	0.0328 (16)	−0.0052 (13)	0.0166 (15)	0.0020 (12)
C1	0.0200 (16)	0.0181 (15)	0.0166 (14)	0.0008 (12)	0.0065 (12)	−0.0002 (12)
C2	0.0168 (15)	0.0205 (15)	0.0204 (14)	−0.0022 (12)	0.0056 (12)	−0.0025 (12)
C3	0.0192 (16)	0.0177 (15)	0.0228 (15)	−0.0005 (12)	0.0056 (13)	0.0006 (13)

Geometric parameters (Å, º) top

Al1—F5	1.757 (2)	N3—C2	1.347 (4)
Al1—F3	1.797 (2)	N3—C3	1.374 (4)
Al1—F4	1.807 (2)	N3—H3	0.8600
Al1—F1	1.807 (2)	N4—C1	1.302 (4)
Al1—F2	1.829 (2)	N4—H4A	0.8600
Al1—O1W	1.929 (2)	N4—H4B	0.8600
O1W—H1W	0.90 (4)	N5—C2	1.299 (4)
O1W—H2W	0.90 (4)	N5—H5A	0.8600
N1—C1	1.334 (4)	N5—H5B	0.8600
N1—C3	1.337 (4)	N6—C3	1.304 (4)
N2—C2	1.342 (4)	N6—H6A	0.8600
N2—C1	1.383 (4)	N6—H6B	0.8600
N2—H2	0.8600

F5—Al1—F3	91.76 (11)	C2—N3—H3	119.5
F5—Al1—F4	93.42 (11)	C3—N3—H3	119.5
F3—Al1—F4	94.23 (10)	C1—N4—H4A	120.0
F5—Al1—F1	91.84 (11)	C1—N4—H4B	120.0
F3—Al1—F1	91.90 (10)	H4A—N4—H4B	120.0
F4—Al1—F1	171.80 (10)	C2—N5—H5A	120.0
F5—Al1—F2	177.98 (12)	C2—N5—H5B	120.0
F3—Al1—F2	88.45 (11)	H5A—N5—H5B	120.0
F4—Al1—F2	88.57 (10)	C3—N6—H6A	120.0
F1—Al1—F2	86.15 (10)	C3—N6—H6B	120.0
F5—Al1—O1W	91.80 (11)	H6A—N6—H6B	120.0
F3—Al1—O1W	176.37 (11)	N4—C1—N1	121.1 (3)
F4—Al1—O1W	86.32 (10)	N4—C1—N2	117.1 (3)
F1—Al1—O1W	87.23 (10)	N1—C1—N2	121.8 (3)
F2—Al1—O1W	87.97 (10)	N5—C2—N2	121.7 (3)
H1W—O1W—H2W	111 (4)	N5—C2—N3	120.7 (3)
C1—N1—C3	117.3 (3)	N2—C2—N3	117.6 (3)
C2—N2—C1	120.6 (3)	N6—C3—N1	120.9 (3)
C2—N2—H2	119.7	N6—C3—N3	117.4 (3)
C1—N2—H2	119.7	N1—C3—N3	121.7 (3)
C2—N3—C3	121.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···N1ⁱ	0.90 (4)	1.94 (5)	2.789 (3)	156 (5)
O1W—H2W···F1ⁱⁱ	0.90 (4)	1.63 (4)	2.515 (3)	169 (5)
N2—H2···F4ⁱⁱⁱ	0.86	1.75	2.601 (3)	169
N3—H3···F2^iv	0.86	2.11	2.871 (3)	148
N3—H3···F3^iv	0.86	2.28	2.990 (3)	140
N3—H3···F1^iv	0.86	2.52	2.953 (4)	112
N4—H4A···F5^v	0.86	2.07	2.763 (3)	138
N4—H4B···F2ⁱⁱⁱ	0.86	1.89	2.739 (3)	168
N5—H5A···F3	0.86	2.06	2.837 (3)	151
N5—H5B···F3^iv	0.86	2.02	2.804 (4)	151
N5—H5B···F4	0.86	2.39	2.863 (3)	115
N6—H6A···F1^vi	0.86	2.04	2.836 (4)	154
N6—H6B···F2^iv	0.86	2.08	2.860 (4)	150

Symmetry codes: (i) x−1, −y+1/2, z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2; (v) −x+1, −y, −z; (vi) x+1, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	(C₃H₈N₆)[AlF₅(H2O)]
M_r	268.13
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.571 (2), 8.823 (2), 13.484 (5)
β (°)	105.53 (3)
V (Å³)	867.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.20 × 0.13 × 0.08

Data collection
Diffractometer	Siemens AED2 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2500, 2500, 1441
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.133, 1.04
No. of reflections	2500
No. of parameters	152
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.48

Computer programs: STADI4 (Stoe & Cie, 1998), X-RED (Stoe & Cie, 1998), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 2005), SHELXL97 (Sheldrick, 2008), enCIFer (Version 1.2; Allen et al., 2004) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···N1ⁱ	0.90 (4)	1.94 (5)	2.789 (3)	156 (5)
O1W—H2W···F1ⁱⁱ	0.90 (4)	1.63 (4)	2.515 (3)	169 (5)
N2—H2···F4ⁱⁱⁱ	0.86	1.75	2.601 (3)	169.2
N3—H3···F2^iv	0.86	2.11	2.871 (3)	147.6
N3—H3···F3^iv	0.86	2.28	2.990 (3)	140.0
N3—H3···F1^iv	0.86	2.52	2.953 (4)	112.3
N4—H4A···F5^v	0.86	2.07	2.763 (3)	137.5
N4—H4B···F2ⁱⁱⁱ	0.86	1.89	2.739 (3)	168.4
N5—H5A···F3	0.86	2.06	2.837 (3)	150.5
N5—H5B···F3^iv	0.86	2.02	2.804 (4)	151.2
N5—H5B···F4	0.86	2.39	2.863 (3)	115.2
N6—H6A···F1^vi	0.86	2.04	2.836 (4)	154.3
N6—H6B···F2^iv	0.86	2.08	2.860 (4)	150.3

Symmetry codes: (i) x−1, −y+1/2, z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2; (v) −x+1, −y, −z; (vi) x+1, −y+1/2, z−1/2.

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Volume 64| Part 4| April 2008| Pages m523-m524

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