Melaminium sulfate.

In the title compound, C(3)H(8)N(6) (2+)·SO(4) (2-), the melaminium cations and sulfate anions are inter-connected by N-H⋯N and N-H⋯O hydrogen bonds, forming a layer in the (101) plane. The layers are connected through multiple hydrogen bonds and π-π stacking inter-actions (centroid-centroid distance of about 3.4 Å).

Related literature

For related literature, see: Janczak & Perpétuo (2001a ▶,b ▶); Martin & Pinkerton (1995 ▶); Dewar et al. (1985 ▶).

Experimental

Crystal data

C3H8N6 2+·SO4 2−

M = 224.21

Monoclinic,

a = 18.5787 (3) Å

b = 8.6272 (2) Å

c = 12.7945 (4) Å

β = 129.739 (1)°

V = 1576.94 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.42 mm−1

T = 293 (2) K

0.32 × 0.27 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (APEX2; Bruker, 2005 ▶) T min = 0.878, T max = 0.900

3793 measured reflections

1794 independent reflections

1672 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.088

S = 1.00

1794 reflections

136 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067463/bt2656sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067463/bt2656Isup2.hkl

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

C3H8N62+·SO42–	F000 = 928
Mr = 224.21	Dx = 1.889 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
a = 18.5787 (3) Å	Cell parameters from 2920 reflections
b = 8.6272 (2) Å	θ = 2.8–27.5º
c = 12.7945 (4) Å	µ = 0.42 mm−1
β = 129.7390 (10)º	T = 293 (2) K
V = 1576.94 (7) Å3	Prism, colorless
Z = 8	0.32 × 0.27 × 0.26 mm

Bruker APEX2 CCD diffractometer	1794 independent reflections
Radiation source: fine-focus sealed tube	1672 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.013
T = 293(2) K	θmax = 27.5º
φ and ω scans	θmin = 2.8º
Absorption correction: multi-scan(APEX2; Bruker, 2005)	h = −24→19
Tmin = 0.879, Tmax = 0.900	k = −6→11
3793 measured reflections	l = −16→16

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.041P)2 + 3.6165P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.089	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.48 e Å−3
1794 reflections	Δρmin = −0.45 e Å−3
136 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (5)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
S1	0.65733 (3)	0.06360 (5)	0.27385 (4)	0.02105 (15)
O2	0.63929 (12)	0.11467 (16)	0.36667 (16)	0.0369 (4)
O4	0.70593 (10)	−0.08710 (15)	0.32413 (17)	0.0348 (4)
C2	0.84604 (12)	0.9717 (2)	0.65207 (17)	0.0210 (3)
N5	0.86032 (10)	0.82418 (17)	0.63479 (15)	0.0215 (3)
N3	0.95352 (12)	1.16685 (18)	0.54108 (18)	0.0312 (4)
H3A	0.9834	1.1488	0.5118	0.037*
H3B	0.9448	1.2607	0.5534	0.037*
O3	0.71951 (10)	0.17704 (15)	0.28119 (15)	0.0309 (3)
N2	0.80592 (11)	1.00382 (18)	0.70342 (17)	0.0277 (3)
H2A	0.7879	0.9301	0.7272	0.033*
H2B	0.7974	1.0988	0.7136	0.033*
C3	0.92125 (12)	1.0513 (2)	0.56700 (18)	0.0222 (3)
N4	0.93490 (11)	0.90603 (17)	0.54780 (16)	0.0236 (3)
N1	0.91024 (13)	0.64908 (18)	0.55885 (18)	0.0317 (4)
H1A	0.9372	0.6259	0.5259	0.038*
H1B	0.8889	0.5768	0.5787	0.038*
O1	0.56934 (11)	0.0514 (2)	0.13681 (16)	0.0440 (4)
N6	0.87638 (11)	1.08607 (18)	0.61675 (16)	0.0232 (3)
C1	0.90174 (12)	0.7934 (2)	0.57868 (17)	0.0219 (3)
H6	0.8684 (18)	1.183 (3)	0.626 (2)	0.042 (7)*
H5	0.8388 (18)	0.749 (3)	0.651 (3)	0.044 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0277 (2)	0.0160 (2)	0.0288 (2)	0.00029 (15)	0.0224 (2)	0.00143 (15)
O2	0.0657 (10)	0.0212 (7)	0.0574 (9)	−0.0009 (7)	0.0549 (9)	−0.0015 (6)
O4	0.0425 (8)	0.0182 (6)	0.0605 (10)	0.0067 (6)	0.0408 (8)	0.0085 (6)
C2	0.0228 (8)	0.0197 (8)	0.0233 (8)	−0.0007 (6)	0.0160 (7)	−0.0004 (6)
N5	0.0284 (7)	0.0166 (7)	0.0289 (7)	−0.0010 (6)	0.0226 (7)	0.0004 (6)
N3	0.0438 (9)	0.0183 (7)	0.0528 (10)	−0.0030 (7)	0.0407 (9)	−0.0011 (7)
O3	0.0416 (8)	0.0189 (6)	0.0502 (8)	−0.0047 (5)	0.0377 (7)	−0.0022 (6)
N2	0.0395 (9)	0.0202 (7)	0.0418 (9)	−0.0002 (6)	0.0345 (8)	−0.0006 (6)
C3	0.0246 (8)	0.0201 (8)	0.0274 (8)	−0.0013 (6)	0.0191 (7)	−0.0010 (6)
N4	0.0296 (8)	0.0185 (7)	0.0345 (8)	−0.0010 (6)	0.0259 (7)	−0.0010 (6)
N1	0.0519 (10)	0.0172 (7)	0.0516 (10)	−0.0016 (7)	0.0449 (9)	−0.0018 (7)
O1	0.0361 (8)	0.0554 (10)	0.0329 (8)	−0.0085 (7)	0.0185 (7)	0.0045 (7)
N6	0.0320 (8)	0.0156 (7)	0.0330 (8)	−0.0002 (6)	0.0259 (7)	−0.0012 (6)
C1	0.0254 (8)	0.0194 (8)	0.0262 (8)	−0.0003 (6)	0.0188 (7)	−0.0007 (6)

S1—O1	1.447 (1)	N3—H3B	0.8600
S1—O3	1.471 (1)	N2—H2A	0.8600
S1—O4	1.475 (1)	N2—H2B	0.8600
S1—O2	1.492 (1)	C3—N4	1.333 (2)
C2—N2	1.300 (2)	C3—N6	1.367 (2)
C2—N5	1.347 (2)	N4—C1	1.338 (2)
C2—N6	1.350 (2)	N1—C1	1.300 (2)
N5—C1	1.373 (2)	N1—H1A	0.8600
N5—H5	0.85 (3)	N1—H1B	0.8600
N3—C3	1.310 (2)	N6—H6	0.87 (3)
N3—H3A	0.8600
O1—S1—O3	111.02 (9)	C2—N2—H2B	120.0
O1—S1—O4	111.51 (10)	H2A—N2—H2B	120.0
O3—S1—O4	108.77 (8)	N3—C3—N4	119.80 (16)
O1—S1—O2	109.36 (10)	N3—C3—N6	117.71 (16)
O3—S1—O2	108.65 (8)	N4—C3—N6	122.46 (16)
O4—S1—O2	107.42 (9)	C3—N4—C1	116.79 (15)
N2—C2—N5	121.41 (16)	C1—N1—H1A	120.0
N2—C2—N6	120.69 (16)	C1—N1—H1B	120.0
N5—C2—N6	117.88 (15)	H1A—N1—H1B	120.0
C2—N5—C1	120.25 (15)	C2—N6—C3	120.35 (15)
C2—N5—H5	120.6 (18)	C2—N6—H6	120.8 (17)
C1—N5—H5	118.9 (19)	C3—N6—H6	118.8 (17)
C3—N3—H3A	120.0	N1—C1—N4	120.09 (16)
C3—N3—H3B	120.0	N1—C1—N5	117.76 (16)
H3A—N3—H3B	120.0	N4—C1—N5	122.13 (15)
C2—N2—H2A	120.0
N2—C2—N5—C1	179.14 (16)	N3—C3—N6—C2	−176.50 (17)
N6—C2—N5—C1	−2.1 (2)	N4—C3—N6—C2	1.8 (3)
N3—C3—N4—C1	178.76 (17)	C3—N4—C1—N1	178.06 (18)
N6—C3—N4—C1	0.5 (3)	C3—N4—C1—N5	−3.6 (3)
N2—C2—N6—C3	177.84 (17)	C2—N5—C1—N1	−177.10 (17)
N5—C2—N6—C3	−0.9 (3)	C2—N5—C1—N4	4.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O2i	0.87 (3)	1.76 (3)	2.622 (2)	171 (3)
N5—H5···O4ii	0.85 (3)	1.76 (3)	2.608 (2)	176 (3)
N3—H3B···O2i	0.86	2.59	3.244 (2)	134
N3—H3B···O1iii	0.86	2.44	2.944 (2)	118
N3—H3A···N4iv	0.86	2.14	3.000 (2)	176
N2—H2B···O3i	0.86	1.97	2.822 (2)	172
N2—H2A···O3v	0.86	2.02	2.836 (2)	159
N1—H1B···O2ii	0.86	1.99	2.838 (2)	169
N1—H1A···O1vi	0.86	2.43	2.992 (2)	123
N1—H1A···O1vii	0.86	2.11	2.887 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯O2i	0.87 (3)	1.76 (3)	2.622 (2)	171 (3)
N5—H5⋯O4ii	0.85 (3)	1.76 (3)	2.608 (2)	176 (3)
N3—H3B⋯O2i	0.86	2.59	3.244 (2)	134
N3—H3B⋯O1iii	0.86	2.44	2.944 (2)	118
N3—H3A⋯N4iv	0.86	2.14	3.000 (2)	176
N2—H2B⋯O3i	0.86	1.97	2.822 (2)	172
N2—H2A⋯O3v	0.86	2.02	2.836 (2)	159
N1—H1B⋯O2ii	0.86	1.99	2.838 (2)	169
N1—H1A⋯O1vi	0.86	2.43	2.992 (2)	123
N1—H1A⋯O1vii	0.86	2.11	2.887 (2)	151

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