2,4,6-Tri-amino-1,3,5-triazin-1-ium 3-(prop-2-eno-yloxy)propano-ate acrylic acid monosolvate monohydrate.

The asymmetric unit of the title salt, C3H7N6 (+)·C6H7O4 (-)·C3H4O2·H2O, contains a 2,4,6-tri-amino-1,3,5-triazin-1-ium cation, a 3-(prop-2-eno-yloxy)propano-ate anion and acrylic acid and water solvent mol-ecules in a 1:1:1:1 ratio and with each species in a general position. In the crystal, the components are linked into a supra-molecular layer in the bc plane via a combination of O-H⋯O, N-H⋯N and N-H⋯O hydrogen bonding. The crystal studied was a non-merohedral twin, the minor component contribution being approximately 26%.

Related literature

For general background to melamine derivatives, see: Krische & Lehn, (2000 ▶). For related structures, see: Kanagathara et al. (2012 ▶); Wang et al. (2007 ▶).

Experimental

Crystal data

C3H7N6 +·C6H7O4 −·C3H4O2·H2O

M = 360.34

Triclinic,

a = 4.84800 (1) Å

b = 12.4200 (2) Å

c = 14.8850 (3) Å

α = 101.010 (1)°

β = 92.652 (1)°

γ = 94.117 (1)°

V = 875.84 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 295 K

0.30 × 0.26 × 0.24 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.973

14152 measured reflections

14152 independent reflections

10635 reflections with I > 2σ(I)

R int = 0.000

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.204

S = 1.07

14152 reflections

264 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009999/tk5217sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009999/tk5217Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009999/tk5217Isup3.cml

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

C3H7N6+·C6H7O4−·C3H4O2·H2O	Z = 2
Mr = 360.34	F(000) = 380
Triclinic, P1	Dx = 1.366 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.84800 (1) Å	Cell parameters from 3859 reflections
b = 12.4200 (2) Å	θ = 2.0–25.0°
c = 14.8850 (3) Å	µ = 0.11 mm−1
α = 101.010 (1)°	T = 295 K
β = 92.652 (1)°	Block, colourless
γ = 94.117 (1)°	0.30 × 0.26 × 0.24 mm
V = 875.84 (3) Å3

Bruker Kappa APEXII CCD diffractometer	14152 independent reflections
Radiation source: fine-focus sealed tube	10635 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
ω and φ scan	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.967, Tmax = 0.973	k = −14→14
14152 measured reflections	l = −17→17

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)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.204	w = 1/[σ2(Fo2) + (0.1084P)2 + 0.3527P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
14152 reflections	Δρmax = 0.40 e Å−3
264 parameters	Δρmin = −0.25 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: 0.011 (2)

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
C1	0.3604 (3)	−0.33906 (13)	0.54291 (10)	0.0388 (4)
C2	0.6285 (3)	−0.25897 (13)	0.45046 (10)	0.0387 (4)
C3	0.3461 (3)	−0.15225 (13)	0.53714 (10)	0.0376 (4)
C4	0.5541 (5)	−0.4187 (2)	0.14464 (17)	0.0881 (7)
H4A	0.6272	−0.4866	0.1297	0.106*
H4B	0.6184	−0.3606	0.1179	0.106*
C5	0.3624 (4)	−0.40507 (17)	0.20271 (14)	0.0658 (6)
H5	0.2942	−0.3361	0.2160	0.079*
C6	0.2452 (4)	−0.49050 (15)	0.24902 (13)	0.0525 (5)
C7	0.7769 (3)	−0.16472 (14)	0.73027 (11)	0.0412 (4)
C8	0.5604 (3)	−0.15879 (14)	0.80048 (11)	0.0461 (4)
H8A	0.4012	−0.2087	0.7746	0.055*
H8B	0.6352	−0.1844	0.8534	0.055*
C9	0.4644 (3)	−0.04632 (15)	0.83200 (12)	0.0501 (5)
H9A	0.4362	−0.0105	0.7802	0.060*
H9B	0.2907	−0.0516	0.8613	0.060*
C10	0.6404 (4)	0.12157 (16)	0.92622 (12)	0.0535 (5)
C11	0.8622 (4)	0.17721 (19)	0.99161 (14)	0.0669 (6)
H11	1.0107	0.1383	1.0049	0.080*
C12	0.8592 (6)	0.2792 (2)	1.03178 (18)	0.1037 (9)
H12A	0.7122	0.3192	1.0192	0.124*
H12B	1.0041	0.3123	1.0732	0.124*
N1	0.2537 (3)	−0.24126 (11)	0.57194 (9)	0.0404 (3)
H1A	0.128 (3)	−0.2424 (18)	0.6135 (11)	0.074 (6)*
N2	0.5509 (3)	−0.35026 (11)	0.48202 (9)	0.0421 (3)
N3	0.5367 (3)	−0.15873 (11)	0.47602 (8)	0.0392 (3)
N4	0.2644 (3)	−0.42345 (13)	0.57764 (11)	0.0536 (4)
H4C	0.323 (3)	−0.4922 (17)	0.5560 (12)	0.057 (5)*
H4D	0.121 (3)	−0.4097 (13)	0.6191 (11)	0.042 (4)*
N5	0.8195 (3)	−0.26917 (14)	0.38830 (9)	0.0467 (4)
H5A	0.899 (4)	−0.3378 (19)	0.3654 (14)	0.081 (7)*
H5B	0.862 (3)	−0.2142 (14)	0.3587 (11)	0.042 (5)*
N6	0.2362 (3)	−0.05879 (13)	0.56754 (11)	0.0492 (4)
H6A	0.110 (4)	−0.0621 (15)	0.6107 (13)	0.055 (5)*
H6B	0.317 (4)	−0.0013 (17)	0.5495 (12)	0.062 (6)*
O1	0.3317 (3)	−0.58757 (11)	0.21954 (9)	0.0694 (4)
H1	0.2598	−0.6320	0.2475	0.104*
O2	0.0843 (3)	−0.47429 (11)	0.30853 (10)	0.0718 (4)
O3	0.8711 (2)	−0.25670 (10)	0.70356 (8)	0.0532 (3)
O4	0.8527 (3)	−0.08094 (10)	0.70184 (8)	0.0563 (3)
O5	0.6780 (2)	0.01609 (10)	0.89658 (8)	0.0518 (3)
O6	0.4413 (3)	0.16469 (12)	0.90105 (11)	0.0773 (4)
O7	1.0138 (4)	0.14515 (14)	0.74741 (12)	0.0742 (4)
H7A	0.915 (5)	0.0873 (16)	0.724 (2)	0.141 (14)*
H7B	1.130 (6)	0.135 (4)	0.787 (2)	0.21 (2)*

	U11	U22	U33	U12	U13	U23
C1	0.0455 (9)	0.0298 (10)	0.0405 (9)	0.0014 (7)	0.0056 (7)	0.0058 (7)
C2	0.0450 (9)	0.0327 (10)	0.0367 (8)	0.0016 (7)	0.0031 (7)	0.0028 (7)
C3	0.0422 (9)	0.0324 (10)	0.0389 (8)	0.0013 (7)	0.0007 (7)	0.0097 (7)
C4	0.115 (2)	0.0604 (16)	0.0961 (17)	0.0067 (13)	0.0356 (16)	0.0270 (13)
C5	0.0868 (15)	0.0412 (13)	0.0705 (13)	0.0073 (10)	0.0062 (12)	0.0123 (10)
C6	0.0622 (12)	0.0352 (11)	0.0585 (11)	0.0059 (9)	−0.0014 (9)	0.0053 (9)
C7	0.0376 (9)	0.0386 (11)	0.0452 (9)	0.0028 (8)	0.0021 (7)	0.0029 (8)
C8	0.0439 (10)	0.0435 (11)	0.0507 (10)	0.0046 (8)	0.0110 (8)	0.0062 (8)
C9	0.0428 (10)	0.0510 (12)	0.0561 (11)	0.0088 (8)	0.0094 (8)	0.0061 (9)
C10	0.0590 (12)	0.0473 (13)	0.0550 (11)	0.0076 (9)	0.0255 (9)	0.0059 (9)
C11	0.0728 (14)	0.0657 (16)	0.0580 (12)	0.0051 (11)	0.0127 (10)	−0.0007 (11)
C12	0.128 (2)	0.075 (2)	0.0941 (19)	0.0066 (16)	−0.0105 (17)	−0.0134 (15)
N1	0.0478 (8)	0.0316 (8)	0.0426 (7)	0.0014 (6)	0.0086 (7)	0.0090 (6)
N2	0.0524 (8)	0.0292 (8)	0.0444 (8)	0.0025 (6)	0.0112 (6)	0.0048 (6)
N3	0.0469 (8)	0.0289 (8)	0.0430 (8)	0.0043 (6)	0.0098 (6)	0.0076 (6)
N4	0.0719 (11)	0.0323 (9)	0.0606 (10)	0.0060 (8)	0.0244 (9)	0.0134 (7)
N5	0.0638 (10)	0.0354 (9)	0.0443 (8)	0.0083 (7)	0.0221 (7)	0.0100 (7)
N6	0.0562 (10)	0.0324 (9)	0.0628 (10)	0.0106 (7)	0.0243 (8)	0.0117 (7)
O1	0.0963 (11)	0.0413 (9)	0.0760 (9)	0.0149 (7)	0.0341 (8)	0.0146 (6)
O2	0.0886 (10)	0.0496 (9)	0.0828 (10)	0.0199 (7)	0.0371 (8)	0.0139 (7)
O3	0.0568 (7)	0.0376 (8)	0.0657 (8)	0.0089 (6)	0.0222 (6)	0.0053 (6)
O4	0.0680 (8)	0.0412 (8)	0.0633 (8)	0.0059 (6)	0.0269 (6)	0.0132 (6)
O5	0.0562 (8)	0.0462 (8)	0.0506 (7)	0.0119 (6)	0.0054 (6)	0.0005 (6)
O6	0.0733 (10)	0.0545 (10)	0.1014 (12)	0.0216 (7)	0.0028 (8)	0.0034 (8)
O7	0.0988 (13)	0.0528 (10)	0.0763 (10)	0.0053 (9)	0.0210 (10)	0.0227 (8)

C1—N4	1.320 (2)	C8—H8B	0.9700
C1—N2	1.3198 (19)	C9—O5	1.451 (2)
C1—N1	1.356 (2)	C9—H9A	0.9700
C2—N5	1.335 (2)	C9—H9B	0.9700
C2—N2	1.344 (2)	C10—O6	1.215 (2)
C2—N3	1.344 (2)	C10—O5	1.329 (2)
C3—N6	1.321 (2)	C10—C11	1.456 (3)
C3—N3	1.3225 (18)	C11—C12	1.294 (3)
C3—N1	1.364 (2)	C11—H11	0.9300
C4—C5	1.296 (3)	C12—H12A	0.9300
C4—H4A	0.9300	C12—H12B	0.9300
C4—H4B	0.9300	N1—H1A	0.889 (9)
C5—C6	1.467 (3)	N4—H4C	0.922 (19)
C5—H5	0.9300	N4—H4D	0.953 (15)
C6—O2	1.205 (2)	N5—H5A	0.97 (2)
C6—O1	1.308 (2)	N5—H5B	0.898 (18)
C7—O4	1.235 (2)	N6—H6A	0.911 (18)
C7—O3	1.2609 (19)	N6—H6B	0.88 (2)
C7—C8	1.511 (2)	O1—H1	0.8200
C8—C9	1.500 (2)	O7—H7A	0.843 (10)
C8—H8A	0.9700	O7—H7B	0.836 (10)
N4—C1—N2	120.99 (15)	O5—C9—H9B	110.3
N4—C1—N1	117.24 (15)	C8—C9—H9B	110.3
N2—C1—N1	121.77 (14)	H9A—C9—H9B	108.5
N5—C2—N2	116.22 (14)	O6—C10—O5	122.83 (18)
N5—C2—N3	117.01 (15)	O6—C10—C11	125.0 (2)
N2—C2—N3	126.76 (14)	O5—C10—C11	112.21 (17)
N6—C3—N3	121.40 (15)	C12—C11—C10	122.1 (2)
N6—C3—N1	116.79 (15)	C12—C11—H11	119.0
N3—C3—N1	121.80 (14)	C10—C11—H11	119.0
C5—C4—H4A	120.0	C11—C12—H12A	120.0
C5—C4—H4B	120.0	C11—C12—H12B	120.0
H4A—C4—H4B	120.0	H12A—C12—H12B	120.0
C4—C5—C6	124.8 (2)	C1—N1—C3	119.00 (13)
C4—C5—H5	117.6	C1—N1—H1A	114.6 (14)
C6—C5—H5	117.6	C3—N1—H1A	126.4 (14)
O2—C6—O1	122.40 (17)	C1—N2—C2	115.50 (13)
O2—C6—C5	124.07 (18)	C3—N3—C2	115.15 (13)
O1—C6—C5	113.53 (17)	C1—N4—H4C	119.3 (11)
O4—C7—O3	123.29 (15)	C1—N4—H4D	116.1 (9)
O4—C7—C8	119.37 (15)	H4C—N4—H4D	124.2 (15)
O3—C7—C8	117.35 (15)	C2—N5—H5A	123.5 (12)
C9—C8—C7	114.76 (15)	C2—N5—H5B	120.4 (10)
C9—C8—H8A	108.6	H5A—N5—H5B	115.5 (16)
C7—C8—H8A	108.6	C3—N6—H6A	114.9 (11)
C9—C8—H8B	108.6	C3—N6—H6B	114.1 (12)
C7—C8—H8B	108.6	H6A—N6—H6B	130.1 (17)
H8A—C8—H8B	107.6	C6—O1—H1	109.5
O5—C9—C8	107.26 (13)	C10—O5—C9	115.98 (13)
O5—C9—H9A	110.3	H7A—O7—H7B	112 (4)
C8—C9—H9A	110.3
C4—C5—C6—O2	173.4 (2)	N4—C1—N2—C2	178.84 (15)
C4—C5—C6—O1	−6.6 (3)	N1—C1—N2—C2	−0.7 (2)
O4—C7—C8—C9	−2.2 (2)	N5—C2—N2—C1	−179.50 (14)
O3—C7—C8—C9	177.86 (15)	N3—C2—N2—C1	1.6 (2)
C7—C8—C9—O5	−77.34 (18)	N6—C3—N3—C2	−179.36 (15)
O6—C10—C11—C12	2.7 (3)	N1—C3—N3—C2	0.8 (2)
O5—C10—C11—C12	−177.0 (2)	N5—C2—N3—C3	179.48 (14)
N4—C1—N1—C3	−179.52 (15)	N2—C2—N3—C3	−1.6 (2)
N2—C1—N1—C3	0.0 (2)	O6—C10—O5—C9	−0.5 (2)
N6—C3—N1—C1	−179.95 (14)	C11—C10—O5—C9	179.17 (14)
N3—C3—N1—C1	−0.1 (2)	C8—C9—O5—C10	174.42 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4	0.84 (1)	2.05 (2)	2.804 (2)	149 (3)
O1—H1···O3i	0.82	1.77	2.5872 (17)	171
N1—H1A···O3ii	0.89 (1)	1.90 (1)	2.7829 (17)	175 (2)
N4—H4C···N2i	0.922 (19)	2.08 (2)	2.995 (2)	175 (16)
N4—H4D···O3ii	0.953 (15)	2.494 (16)	3.295 (2)	142 (12)
N4—H4D···O2iii	0.953 (15)	2.172 (15)	2.850 (2)	127 (12)
N5—H5A···O2iv	0.97 (2)	2.03 (2)	3.001 (2)	175 (17)
N5—H5B···O7v	0.898 (18)	2.031 (18)	2.875 (2)	156 (14)
N6—H6B···N3vi	0.88 (2)	2.17 (2)	3.039 (2)	169 (17)
O7—H7B···O6iv	0.84 (1)	2.17 (2)	2.977 (3)	161 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O4	0.84 (1)	2.05 (2)	2.804 (2)	149 (3)
O1—H1⋯O3i	0.82	1.77	2.5872 (17)	171
N1—H1A⋯O3ii	0.89 (1)	1.90 (1)	2.7829 (17)	175 (2)
N4—H4C⋯N2i	0.922 (19)	2.08 (2)	2.995 (2)	175 (16)
N4—H4D⋯O3ii	0.953 (15)	2.494 (16)	3.295 (2)	142 (12)
N4—H4D⋯O2iii	0.953 (15)	2.172 (15)	2.850 (2)	127 (12)
N5—H5A⋯O2iv	0.97 (2)	2.03 (2)	3.001 (2)	175 (17)
N5—H5B⋯O7v	0.898 (18)	2.031 (18)	2.875 (2)	156 (14)
N6—H6B⋯N3vi	0.88 (2)	2.17 (2)	3.039 (2)	169 (17)
O7—H7B⋯O6iv	0.84 (1)	2.17 (2)	2.977 (3)	161 (4)

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