2,4,6-Tri­amino-1,3,5-triazin-1-ium 3-(prop-2-eno­yloxy)propano­ate acrylic acid monosolvate monohydrate

Sangeetha, V.; Kanagathara, N.; Chakkaravarthi, G.; Marchewka, M.K.; Anbalagan, G.

doi:10.1107/S1600536813009999

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o741

https://doi.org/10.1107/S1600536813009999

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2,4,6-Triamino-1,3,5-triazin-1-ium 3-(prop-2-enoyloxy)propanoate acrylic acid monosolvate monohydrate

V. Sangeetha,^a N. Kanagathara,^b G. Chakkaravarthi,^c ^* M. K. Marchewka ^d and G. Anbalagan ^e ^*

^aDepartment of Physics, D.G. Vaishnav College, Chennai 600 106, India, ^bDepartment of Physics, Vel Tech Multi Tech Dr. Rangarajan and Dr. Sakunthala Eng. College, Chennai 600 062, India, ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^dInstitute of Low Temperature and Structure Research, Polish Academy of Sciences, 50-950 Wrocław, 2, PO Box 937, Poland, and ^eDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, anbu_24663@yahoo.co.in

(Received 9 April 2013; accepted 11 April 2013; online 17 April 2013)

The asymmetric unit of the title salt, C₃H₇N₆⁺·C₆H₇O₄⁻·C₃H₄O₂·H₂O, contains a 2,4,6-triamino-1,3,5-triazin-1-ium cation, a 3-(prop-2-enoyloxy)propanoate anion and acrylic acid and water solvent molecules in a 1:1:1:1 ratio and with each species in a general position. In the crystal, the components are linked into a supramolecular 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_r = 360.34
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.059
wR(F²) = 0.204
S = 1.07
14152 reflections
264 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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⋯O2^iv	0.97 (2)	2.03 (2)	3.001 (2)	175 (17)
N5—H5B⋯O7^v	0.898 (18)	2.031 (18)	2.875 (2)	156 (14)
N6—H6B⋯N3^vi	0.88 (2)	2.17 (2)	3.039 (2)	169 (17)
O7—H7B⋯O6^iv	0.84 (1)	2.17 (2)	2.977 (3)	161 (4)
Symmetry codes: (i) -x+1, -y-1, -z+1; (ii) x-1, y, z; (iii) -x, -y-1, -z+1; (iv) x+1, y, z; (v) -x+2, -y, -z+1; (vi) -x+1, -y, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813009999/tk5217sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009999/tk5217Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813009999/tk5217Isup3.cml

checkCIF report

Comment top

Melamine and its derivatives can develop well defined non-covalent supramolecular nanoarchitectures via multiple hydrogen bonds by self-assembly of components containing complementary arrays of hydrogen-bonding sites (Krische & Lehn, 2000). The geometric parameters of the title compound (I), Fig. 1, are comparable with similar structures (Kanagathara et al., 2012; Wang et al., 2007).

The crystal packing is stabilized by intermolecular O—H···O, N—H···O, N—H···N and C—H···O interactions to form layers in the bc-plane, Fig. 2.

Related literature top

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

Experimental top

Melamine (0.64 g, 5 mmol) and acrylic acid (0.36 g, 5 mmol) were taken in 1:3 ratio. Melamine was dissolved in a hot solution (100 ml) of distilled water. Acrylic acid (1.3911 g, 0.01 mmol) was dissolved in distilled water (5 ml) separately. To the hot solution of melamine, the acrylic acid solution was added slowly, and stirred well for nearly four hours to get a homogeneous solution. Then, the mixture is allowed to evaporate. After several days, transparent crystals suitable for X-ray diffractions were formed.

Structure description top

The crystal packing is stabilized by intermolecular O—H···O, N—H···O, N—H···N and C—H···O interactions to form layers in the bc-plane, Fig. 2.

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

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the constituents of (I), showing atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A view of the packing of (I) in projection down the a axis. Hydrogen bonds are shown as dashed lines.

2,4,6-Triamino-1,3,5-triazin-1-ium 3-(prop-2-enoyloxy)propanoate acrylic acid monosolvate monohydrate top

Crystal data top

C₃H₇N₆⁺·C₆H₇O₄⁻·C₃H₄O₂·H₂O	Z = 2
M_r = 360.34	F(000) = 380
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1084P)² + 0.3527P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
14152 reflections	Δρ_max = 0.40 e Å⁻³
264 parameters	Δρ_min = −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)

Crystal data top

C₃H₇N₆⁺·C₆H₇O₄⁻·C₃H₄O₂·H₂O	γ = 94.117 (1)°
M_r = 360.34	V = 875.84 (3) Å³
Triclinic, P1	Z = 2
a = 4.84800 (1) Å	Mo Kα radiation
b = 12.4200 (2) Å	µ = 0.11 mm⁻¹
c = 14.8850 (3) Å	T = 295 K
α = 101.010 (1)°	0.30 × 0.26 × 0.24 mm
β = 92.652 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	14152 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	10635 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.973	R_int = 0.000
14152 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	3 restraints
wR(F²) = 0.204	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.40 e Å⁻³
14152 reflections	Δρ_min = −0.25 e Å⁻³
264 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.97 (2)	2.03 (2)	3.001 (2)	175 (17)
N5—H5B···O7^v	0.898 (18)	2.031 (18)	2.875 (2)	156 (14)
N6—H6B···N3^vi	0.88 (2)	2.17 (2)	3.039 (2)	169 (17)
O7—H7B···O6^iv	0.84 (1)	2.17 (2)	2.977 (3)	161 (4)

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

Experimental details

Crystal data
Chemical formula	C₃H₇N₆⁺·C₆H₇O₄⁻·C₃H₄O₂·H₂O
M_r	360.34
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	4.84800 (1), 12.4200 (2), 14.8850 (3)
α, β, γ (°)	101.010 (1), 92.652 (1), 94.117 (1)
V (Å³)	875.84 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.26 × 0.24

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.967, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	14152, 14152, 10635
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.204, 1.07
No. of reflections	14152
No. of parameters	264
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.25

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4	0.843 (10)	2.050 (19)	2.804 (2)	149 (3)
O1—H1···O3ⁱ	0.82	1.77	2.5872 (17)	171
N1—H1A···O3ⁱⁱ	0.889 (9)	1.896 (10)	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···O2^iv	0.97 (2)	2.03 (2)	3.001 (2)	175 (17)
N5—H5B···O7^v	0.898 (18)	2.031 (18)	2.875 (2)	156 (14)
N6—H6B···N3^vi	0.88 (2)	2.17 (2)	3.039 (2)	169 (17)
O7—H7B···O6^iv	0.836 (10)	2.173 (17)	2.977 (3)	161 (4)

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

Acknowledgements

The authors wish to acknowledge the SAIF, IIT Madras, for the data collection.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kanagathara, N., Chakkaravarthi, G., Marchewka, M. K., Gunasekaran, S. & Anbalagan, G. (2012). Acta Cryst. E68, o2286. CSD CrossRef IUCr Journals Google Scholar
Krische, M. J. & Lehn, J. M. (2000). Struct. Bond. 96, 3–29. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, G., Wu, W. & Zhuang, L. (2007). Acta Cryst. E63, m2552–m2553. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,4,6-Tri­amino-1,3,5-triazin-1-ium 3-(prop-2-eno­yl­oxy)propano­ate acrylic acid monosolvate monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,4,6-Triamino-1,3,5-triazin-1-ium 3-(prop-2-enoyloxy)propanoate acrylic acid monosolvate monohydrate