Bis(melaminium) succinate succinic acid monosolvate dihydrate.

The asymmetric unit of the solvated title salt, 2C(3)H(7)N(6) (+)·C(4)H(4)O(4) (2-)·C(4)H(6)O(4)·2H(2)O, contains one essentially planar melaminium (2,4,6-triamino-1,3,5-triazin-1-ium) cation (r.m.s. deviation of the non-H atoms = 0.0097 Å), one-half of a succinate anion, one-half of a succinic acid solvent mol-ecule and one water molecule of crystallization; full mol-ecules are generated by inversion symmetry. Supra-molecular layers parallel to (12-1) are formed through extensive inter-molecular hydrogen bonding of the types O-H⋯O, N-H⋯N and N-H⋯O between the components.

Related literature

For the use of melaminium salts in polymer science, see: Weinstabl et al. (2001 ▶). For a list of structurally determined n class="Chemical">melaminium salts of purely organic carb­oxy­lic acids, see: Froschauer & Weil (2012 ▶).

Experimental

Crystal data

2C3H7N6 +·n class="Chemical">C4H4O4 2−·C4H6O4·2H2O

M = 524.48

Triclinic,

a = 7.1193 (7) Å

b = 8.1650 (8) Å

c = 9.5595 (9) Å

α = 88.013 (2)°

β = 84.647 (2)°

γ = 88.093 (2)°

V = 552.68 (9) Å3

Z = 1

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.23 × 0.18 × 0.12 mm

Data collection

Siemens SMART CCD diffractometer

5533 measured reflections

2719 independent reflections

1545 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.142

S = 0.97

2719 reflections

173 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶) and ATOMS (Dowty, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033387/cv5324sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033387/cv5324Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033387/cv5324Isup3.cml

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

2C3H7N6+·C4H4O42−·C4H6O4·2H2O	Z = 1
Mr = 524.48	F(000) = 276
Triclinic, P1	Dx = 1.576 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1193 (7) Å	Cell parameters from 1570 reflections
b = 8.1650 (8) Å	θ = 2.5–28.8°
c = 9.5595 (9) Å	µ = 0.13 mm−1
α = 88.013 (2)°	T = 293 K
β = 84.647 (2)°	Parallelepiped, colourless
γ = 88.093 (2)°	0.23 × 0.18 × 0.12 mm
V = 552.68 (9) Å3

Siemens SMART CCD diffractometer	1545 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 28.3°, θmin = 2.1°
ω scans	h = −9→9
5533 measured reflections	k = −10→10
2719 independent reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0791P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
2719 reflections	Δρmax = 0.30 e Å−3
173 parameters	Δρmin = −0.26 e Å−3
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (4)

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
N3	0.3081 (2)	1.0330 (2)	0.36672 (15)	0.0308 (4)
N1	0.4064 (2)	0.8895 (2)	0.16163 (15)	0.0323 (4)
H1	0.4894	0.8279	0.1160	0.039*
O1	0.62741 (19)	0.68205 (18)	−0.02657 (14)	0.0385 (4)
O3	0.6682 (2)	0.2996 (2)	0.25900 (15)	0.0456 (4)
O2	0.8071 (2)	0.6984 (2)	0.14806 (15)	0.0480 (5)
O4	0.3997 (2)	0.44613 (19)	0.26505 (14)	0.0431 (4)
C7	0.5535 (3)	0.3930 (3)	0.3191 (2)	0.0309 (5)
C1	0.2450 (3)	0.9365 (2)	0.10469 (19)	0.0284 (4)
N2	0.1121 (2)	1.0287 (2)	0.17327 (15)	0.0305 (4)
C2	0.1488 (3)	1.0729 (2)	0.30373 (18)	0.0281 (4)
C6	0.5839 (3)	0.4567 (3)	0.46117 (19)	0.0339 (5)
H6A	0.6871	0.5321	0.4491	0.041*
H6B	0.6233	0.3651	0.5200	0.041*
N4	0.2251 (2)	0.8874 (2)	−0.02317 (16)	0.0370 (4)
H3	0.1250	0.9151	−0.0632	0.044*
H2	0.3123	0.8277	−0.0664	0.044*
N6	0.5975 (2)	0.8950 (2)	0.34112 (18)	0.0402 (5)
H6	0.6226	0.9242	0.4228	0.048*
H7	0.6778	0.8356	0.2909	0.048*
C3	0.4365 (3)	0.9412 (2)	0.29314 (19)	0.0301 (5)
C4	0.7771 (3)	0.6435 (2)	0.0324 (2)	0.0308 (5)
N5	0.0177 (2)	1.1639 (2)	0.37353 (17)	0.0396 (5)
H5	0.0347	1.1959	0.4561	0.048*
H4	−0.0848	1.1912	0.3365	0.048*
O1W	0.0343 (3)	0.6661 (3)	0.36216 (18)	0.0637 (6)
H1W	0.126 (4)	0.591 (3)	0.353 (3)	0.097*
H2W	−0.024 (4)	0.667 (4)	0.288 (2)	0.097*
H12	0.385 (4)	0.393 (3)	0.171 (2)	0.097*
C5	0.9192 (3)	0.5292 (3)	−0.04228 (19)	0.0306 (5)
H5A	0.9717	0.5841	−0.1280	0.037*
H5B	0.8543	0.4341	−0.0690	0.037*

	U11	U22	U33	U12	U13	U23
N3	0.0277 (9)	0.0441 (10)	0.0218 (8)	0.0109 (8)	−0.0092 (7)	−0.0101 (7)
N1	0.0283 (9)	0.0444 (10)	0.0248 (8)	0.0147 (8)	−0.0070 (7)	−0.0131 (7)
O1	0.0295 (8)	0.0537 (10)	0.0344 (8)	0.0173 (7)	−0.0150 (6)	−0.0151 (7)
O3	0.0392 (9)	0.0659 (11)	0.0337 (8)	0.0230 (8)	−0.0151 (7)	−0.0236 (7)
O2	0.0455 (9)	0.0664 (11)	0.0351 (8)	0.0258 (8)	−0.0193 (7)	−0.0285 (8)
O4	0.0381 (9)	0.0635 (11)	0.0303 (8)	0.0209 (7)	−0.0178 (6)	−0.0191 (7)
C7	0.0278 (10)	0.0395 (12)	0.0261 (9)	0.0081 (9)	−0.0067 (8)	−0.0069 (8)
C1	0.0269 (10)	0.0366 (11)	0.0222 (9)	0.0051 (8)	−0.0061 (8)	−0.0061 (8)
N2	0.0281 (9)	0.0428 (10)	0.0217 (8)	0.0076 (7)	−0.0085 (7)	−0.0097 (7)
C2	0.0250 (10)	0.0386 (11)	0.0215 (9)	0.0063 (8)	−0.0062 (8)	−0.0067 (8)
C6	0.0296 (11)	0.0479 (13)	0.0257 (10)	0.0076 (9)	−0.0106 (8)	−0.0085 (9)
N4	0.0332 (9)	0.0548 (12)	0.0245 (8)	0.0131 (8)	−0.0107 (7)	−0.0169 (8)
N6	0.0330 (10)	0.0596 (12)	0.0295 (9)	0.0231 (9)	−0.0130 (7)	−0.0173 (8)
C3	0.0301 (10)	0.0372 (12)	0.0243 (9)	0.0055 (9)	−0.0095 (8)	−0.0070 (8)
C4	0.0282 (10)	0.0357 (11)	0.0294 (10)	0.0105 (9)	−0.0083 (8)	−0.0083 (8)
N5	0.0322 (9)	0.0630 (13)	0.0255 (8)	0.0174 (9)	−0.0127 (7)	−0.0182 (8)
O1W	0.0646 (12)	0.0902 (15)	0.0408 (9)	0.0294 (10)	−0.0287 (8)	−0.0315 (9)
C5	0.0299 (10)	0.0388 (12)	0.0243 (9)	0.0108 (9)	−0.0087 (8)	−0.0104 (8)

N3—C3	1.328 (2)	C6—H6A	0.9700
N3—C2	1.358 (2)	C6—H6B	0.9700
N1—C1	1.356 (2)	N4—H3	0.8600
N1—C3	1.378 (2)	N4—H2	0.8600
N1—H1	0.8600	N6—C3	1.313 (2)
O1—C4	1.277 (2)	N6—H6	0.8600
O3—C7	1.217 (2)	N6—H7	0.8600
O2—C4	1.246 (2)	C4—C5	1.500 (3)
O4—C7	1.309 (2)	N5—H5	0.8600
O4—H12	1.023 (17)	N5—H4	0.8600
C7—C6	1.507 (3)	O1W—H1W	0.882 (17)
C1—N4	1.321 (2)	O1W—H2W	0.856 (18)
C1—N2	1.328 (2)	C5—C5ii	1.522 (3)
N2—C2	1.361 (2)	C5—H5A	0.9700
C2—N5	1.319 (2)	C5—H5B	0.9700
C6—C6i	1.514 (4)
C3—N3—C2	115.93 (15)	C1—N4—H2	120.0
C1—N1—C3	119.48 (16)	H3—N4—H2	120.0
C1—N1—H1	120.3	C3—N6—H6	120.0
C3—N1—H1	120.3	C3—N6—H7	120.0
C7—O4—H12	111.6 (17)	H6—N6—H7	120.0
O3—C7—O4	122.87 (17)	N6—C3—N3	122.22 (17)
O3—C7—C6	121.05 (18)	N6—C3—N1	116.61 (17)
O4—C7—C6	116.07 (17)	N3—C3—N1	121.17 (17)
N4—C1—N2	120.96 (17)	O2—C4—O1	121.88 (17)
N4—C1—N1	117.14 (17)	O2—C4—C5	120.22 (17)
N2—C1—N1	121.90 (16)	O1—C4—C5	117.90 (16)
C1—N2—C2	115.70 (16)	C2—N5—H5	120.0
N5—C2—N3	117.76 (16)	C2—N5—H4	120.0
N5—C2—N2	116.44 (16)	H5—N5—H4	120.0
N3—C2—N2	125.80 (17)	H1W—O1W—H2W	107 (3)
C7—C6—C6i	116.3 (2)	C4—C5—C5ii	115.00 (19)
C7—C6—H6A	108.2	C4—C5—H5A	108.5
C6i—C6—H6A	108.2	C5ii—C5—H5A	108.5
C7—C6—H6B	108.2	C4—C5—H5B	108.5
C6i—C6—H6B	108.2	C5ii—C5—H5B	108.5
H6A—C6—H6B	107.4	H5A—C5—H5B	107.5
C1—N4—H3	120.0

D—H···A	D—H	H···A	D···A	D—H···A
N4—H3···N2iii	0.86	2.10	2.959 (2)	176
N1—H1···O1	0.86	2.01	2.844 (2)	164
N5—H4···O3iv	0.86	2.13	2.976 (2)	170
N6—H6···N3v	0.86	2.16	3.015 (2)	173
N1—H1···O2	0.86	2.50	3.199 (2)	138
N4—H2···O3vi	0.86	2.14	2.799 (2)	134
N4—H2···O1	0.86	2.56	3.268 (2)	141
N6—H7···O2	0.86	1.94	2.782 (2)	166
N5—H5···O1Wvii	0.86	2.11	2.912 (2)	154
O1W—H1W···O4	0.88 (2)	2.35 (2)	3.195 (2)	162 (3)
O1W—H2W···O2viii	0.86 (2)	1.89 (2)	2.726 (2)	167 (3)
O4—H12···O1vi	1.02 (2)	1.55 (2)	2.5673 (19)	177 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H3⋯N2i	0.86	2.10	2.959 (2)	176
N1—H1⋯O1	0.86	2.01	2.844 (2)	164
N5—H4⋯O3ii	0.86	2.13	2.976 (2)	170
N6—H6⋯N3iii	0.86	2.16	3.015 (2)	173
N1—H1⋯O2	0.86	2.50	3.199 (2)	138
N4—H2⋯O3iv	0.86	2.14	2.799 (2)	134
N4—H2⋯O1	0.86	2.56	3.268 (2)	141
N6—H7⋯O2	0.86	1.94	2.782 (2)	166
N5—H5⋯O1W v	0.86	2.11	2.912 (2)	154
O1W—H1W⋯O4	0.88 (2)	2.35 (2)	3.195 (2)	162 (3)
O1W—H2W⋯O2vi	0.86 (2)	1.89 (2)	2.726 (2)	167 (3)
O4—H12⋯O1iv	1.02 (2)	1.55 (2)	2.5673 (19)	177 (3)

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