Melaminium perchlorate monohydrate.

In the title hydrated salt, 2,4,6-triamino-1,3,5-triazin-1-ium perchlorate monohydrate, C(3)H(7)N(6) (+)·ClO(4) (-)·H(2)O, the constituents are linked via hydrogen bonds of the O-H⋯O, N-H⋯O, N-H⋯N and N-H⋯Cl types. All the H atoms of the melaminium cation are involved in the hydrogen bonds. The melaminium residues are inter-connected by four N-H⋯N hydrogen bonds, forming chains parallel to (111). The ribbons are inter-connected by other hydrogen bonds as well as by π-π inter-actions [centroid-centroid distance = 3.8097 (7) Å].

Related literature

For similar organic acid–base compounds, see: Martin & Pinkerton (1995 ▶); Perpétuo & Janczak (2006 ▶). For their ferroelectric properties, see: Hang et al. (2009 ▶), Li et al. (2008 ▶). For impedance studies, see; Uthrakumar et al. (2008 ▶).

Experimental

Crystal data

C3H7N6 +·ClO4 −·H2O

M = 244.61

Triclinic,

a = 5.654 (4) Å

b = 7.553 (7) Å

c = 11.893 (10) Å

α = 102.72 (4)°

β = 94.58 (3)°

γ = 110.78 (2)°

V = 456.1 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.44 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.916, T max = 0.916

4902 measured reflections

2051 independent reflections

1719 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.091

S = 0.90

2051 reflections

163 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001857X/ng2764sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001857X/ng2764Isup2.hkl

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

C3H7N6+·ClO4−·H2O	Z = 2
Mr = 244.61	F(000) = 252
Triclinic, P1	Dx = 1.781 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.654 (4) Å	Cell parameters from 1388 reflections
b = 7.553 (7) Å	θ = 3.0–27.6°
c = 11.893 (10) Å	µ = 0.44 mm−1
α = 102.72 (4)°	T = 293 K
β = 94.58 (3)°	Prism, colorless
γ = 110.78 (2)°	0.20 × 0.20 × 0.20 mm
V = 456.1 (7) Å3

Rigaku SCXmini diffractometer	2051 independent reflections
Radiation source: fine-focus sealed tube	1719 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.0°
CCD_Profile_fitting scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.916, Tmax = 0.916	l = −15→14
4902 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ2(Fo2) + (0.0659P)2 + 0.0106P] where P = (Fo2 + 2Fc2)/3
2051 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.29 e Å−3
10 restraints	Δρmin = −0.41 e Å−3

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

	x	y	z	Uiso*/Ueq
C1	0.5601 (3)	0.8552 (2)	0.63004 (14)	0.0133 (3)
C2	0.7940 (3)	0.7067 (2)	0.53001 (14)	0.0129 (3)
C3	0.7094 (3)	0.6425 (2)	0.70349 (14)	0.0130 (3)
O1	1.0855 (2)	1.12497 (17)	0.75979 (9)	0.0166 (3)
O2	1.1733 (2)	1.45744 (17)	0.84904 (11)	0.0201 (3)
O3	0.8606 (3)	1.2106 (2)	0.90661 (11)	0.0274 (3)
O4	1.2993 (3)	1.26696 (19)	0.95543 (11)	0.0244 (3)
O5	1.3200 (3)	0.87257 (18)	0.88354 (10)	0.0196 (3)
H5B	1.346 (4)	0.9895 (10)	0.9193 (14)	0.023*
H5A	1.259 (4)	0.7975 (19)	0.9260 (13)	0.023*
Cl1	1.10439 (7)	1.26476 (5)	0.86874 (3)	0.01324 (13)
N1	0.4347 (3)	0.9749 (2)	0.64603 (13)	0.0172 (3)
H1B	0.357 (3)	0.990 (3)	0.7040 (12)	0.021*
H1A	0.409 (4)	1.034 (3)	0.5952 (13)	0.021*
N2	0.7213 (3)	0.5547 (2)	0.78757 (13)	0.0169 (3)
H2B	0.657 (4)	0.576 (3)	0.8500 (11)	0.020*
H2A	0.818 (3)	0.489 (3)	0.7840 (16)	0.020*
N3	0.8987 (3)	0.6748 (2)	0.43553 (13)	0.0162 (3)
H3B	0.975 (3)	0.594 (2)	0.4283 (17)	0.019*
H3A	0.890 (4)	0.741 (3)	0.3865 (13)	0.019*
N4	0.5745 (3)	0.7610 (2)	0.71408 (11)	0.0131 (3)
H4A	0.500 (3)	0.784 (3)	0.7707 (11)	0.016*
N5	0.8221 (3)	0.61161 (19)	0.61130 (11)	0.0131 (3)
N6	0.6663 (3)	0.8296 (2)	0.53570 (11)	0.0129 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0126 (7)	0.0127 (7)	0.0130 (8)	0.0043 (6)	0.0003 (6)	0.0015 (6)
C2	0.0130 (7)	0.0121 (7)	0.0118 (8)	0.0041 (6)	0.0006 (6)	0.0012 (6)
C3	0.0115 (7)	0.0123 (7)	0.0136 (8)	0.0036 (6)	0.0014 (6)	0.0024 (6)
O1	0.0217 (6)	0.0173 (6)	0.0111 (6)	0.0095 (5)	0.0030 (5)	0.0008 (5)
O2	0.0241 (7)	0.0143 (6)	0.0249 (7)	0.0091 (5)	0.0061 (5)	0.0073 (5)
O3	0.0210 (7)	0.0342 (8)	0.0240 (7)	0.0048 (6)	0.0153 (6)	0.0072 (6)
O4	0.0325 (8)	0.0254 (7)	0.0162 (6)	0.0170 (6)	−0.0064 (5)	0.0012 (5)
O5	0.0282 (7)	0.0153 (6)	0.0185 (6)	0.0093 (5)	0.0111 (5)	0.0067 (5)
Cl1	0.0151 (2)	0.0145 (2)	0.0113 (2)	0.00664 (15)	0.00399 (14)	0.00364 (15)
N1	0.0233 (8)	0.0230 (8)	0.0138 (7)	0.0167 (6)	0.0076 (6)	0.0069 (6)
N2	0.0202 (8)	0.0240 (8)	0.0151 (7)	0.0145 (6)	0.0089 (6)	0.0099 (6)
N3	0.0240 (8)	0.0194 (7)	0.0136 (7)	0.0151 (6)	0.0082 (6)	0.0077 (6)
N4	0.0151 (7)	0.0163 (7)	0.0102 (7)	0.0079 (6)	0.0060 (5)	0.0039 (6)
N5	0.0154 (7)	0.0146 (7)	0.0119 (7)	0.0079 (6)	0.0040 (5)	0.0044 (5)
N6	0.0159 (7)	0.0145 (6)	0.0103 (7)	0.0084 (6)	0.0028 (5)	0.0029 (5)

C1—N6	1.324 (2)	O3—Cl1	1.4318 (16)
C1—N1	1.325 (2)	O4—Cl1	1.4406 (16)
C1—N4	1.362 (2)	O5—H5B	0.845 (5)
C2—N3	1.327 (2)	O5—H5A	0.843 (5)
C2—N5	1.356 (2)	N1—H1B	0.855 (5)
C2—N6	1.357 (2)	N1—H1A	0.860 (5)
C3—N2	1.325 (2)	N2—H2B	0.861 (5)
C3—N5	1.329 (2)	N2—H2A	0.859 (5)
C3—N4	1.360 (2)	N3—H3B	0.854 (5)
O1—Cl1	1.4493 (16)	N3—H3A	0.855 (5)
O2—Cl1	1.4446 (18)	N4—H4A	0.840 (5)
N6—C1—N1	120.73 (15)	O2—Cl1—O1	108.79 (9)
N6—C1—N4	121.88 (15)	C1—N1—H1B	123.3 (14)
N1—C1—N4	117.39 (15)	C1—N1—H1A	123.2 (14)
N3—C2—N5	116.85 (15)	H1B—N1—H1A	113.2 (19)
N3—C2—N6	117.06 (15)	C3—N2—H2B	122.9 (13)
N5—C2—N6	126.09 (15)	C3—N2—H2A	117.4 (13)
N2—C3—N5	120.63 (15)	H2B—N2—H2A	118.9 (18)
N2—C3—N4	117.70 (15)	C2—N3—H3B	119.0 (13)
N5—C3—N4	121.65 (15)	C2—N3—H3A	116.9 (13)
H5B—O5—H5A	109.5 (11)	H3B—N3—H3A	124.0 (19)
O3—Cl1—O4	110.66 (10)	C3—N4—C1	119.41 (14)
O3—Cl1—O2	109.04 (8)	C3—N4—H4A	124.6 (13)
O4—Cl1—O2	109.67 (9)	C1—N4—H4A	116.0 (13)
O3—Cl1—O1	109.34 (9)	C3—N5—C2	115.48 (14)
O4—Cl1—O1	109.31 (9)	C1—N6—C2	115.45 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O4	0.85 (1)	2.16 (1)	2.960 (3)	158 (2)
O5—H5B···O5i	0.85 (1)	2.64 (2)	3.081 (3)	114 (2)
O5—H5A···O3ii	0.84 (1)	2.16 (1)	2.883 (3)	144 (2)
O5—H5A···O2iii	0.84 (1)	2.38 (2)	2.867 (3)	117 (1)
N1—H1B···O1iv	0.86 (1)	2.19 (1)	2.890 (2)	139 (2)
N1—H1B···O5iv	0.86 (1)	2.48 (2)	3.146 (3)	135 (2)
N1—H1A···N6v	0.86 (1)	2.14 (1)	2.998 (3)	178 (2)
N2—H2B···O4ii	0.86 (1)	2.31 (1)	3.086 (3)	151 (2)
N2—H2B···O2vi	0.86 (1)	2.56 (2)	3.108 (3)	123 (2)
N2—H2A···O2iii	0.86 (1)	2.20 (1)	2.979 (3)	150 (2)
N2—H2A···Cl1iii	0.86 (1)	2.99 (1)	3.792 (3)	157 (2)
N3—H3B···N5vii	0.85 (1)	2.23 (1)	3.084 (3)	173 (2)
N3—H3A···O1viii	0.86 (1)	2.19 (1)	3.029 (3)	168 (2)
N4—H4A···O5iv	0.84 (1)	1.90 (1)	2.723 (2)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯O4	0.85 (1)	2.16 (1)	2.960 (3)	158 (2)
O5—H5B⋯O5i	0.85 (1)	2.64 (2)	3.081 (3)	114 (2)
O5—H5A⋯O3ii	0.84 (1)	2.16 (1)	2.883 (3)	144 (2)
O5—H5A⋯O2iii	0.84 (1)	2.38 (2)	2.867 (3)	117 (1)
N1—H1B⋯O1iv	0.86 (1)	2.19 (1)	2.890 (2)	139 (2)
N1—H1B⋯O5iv	0.86 (1)	2.48 (2)	3.146 (3)	135 (2)
N1—H1A⋯N6v	0.86 (1)	2.14 (1)	2.998 (3)	178 (2)
N2—H2B⋯O4ii	0.86 (1)	2.31 (1)	3.086 (3)	151 (2)
N2—H2B⋯O2vi	0.86 (1)	2.56 (2)	3.108 (3)	123 (2)
N2—H2A⋯O2iii	0.86 (1)	2.20 (1)	2.979 (3)	150 (2)
N2—H2A⋯Cl1iii	0.86 (1)	2.99 (1)	3.792 (3)	157 (2)
N3—H3B⋯N5vii	0.85 (1)	2.23 (1)	3.084 (3)	173 (2)
N3—H3A⋯O1viii	0.86 (1)	2.19 (1)	3.029 (3)	168 (2)
N4—H4A⋯O5iv	0.84 (1)	1.90 (1)	2.723 (2)	168 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .