Guanidinium 3-carb­oxy-2,3-dihydroxy­propanoate monohydrate

Al-Dajani, M.T.M.; Abdallah, H.H.; Mohamed, N.; Goh, J.H.; Fun, H.-K.

doi:10.1107/S1600536809037313

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages o2508-o2509

doi:10.1107/S1600536809037313

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Guanidinium 3-carboxy-2,3-dihydroxypropanoate monohydrate

Mohammad T. M. Al-Dajani,^a Hassan H. Abdallah,^b Nornisah Mohamed,^a ^* Jia Hao Goh ^c and Hoong-Kun Fun ^c ^*‡

^aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: nornisah@usm.my, hkfun@usm.my

(Received 14 September 2009; accepted 15 September 2009; online 19 September 2009)

In the title hydrated salt, CH₆N₃⁺·C₄H₅O₆⁻·H₂O, the deprotonated carboxyl group is disordered over two positions with a site-occupancy ratio of 0.945 (3):0.055 (3). The bond lengths in the guanidinium cation are intermediate between normal C—N and C=N bond lengths, indicating significant delocalization in this species. In the crystal structure, anions and water molecules are linked into sheets parallel to the ab plane by intermolecular O—H⋯O hydrogen bonds. The linking of the anions and water molecules with the cations by intermolecular N—H⋯O hydrogen bonds creates a three-dimensional network.

Related literature

For general background to and applications of guanidine derivatives, see: Angyal & Warburton (1951 ); Raczyńska et al. (2003 ); Yamada et al. (2009 ). For closely related guanidinium structures, see: Najafpour et al. (2007 ); Pereira Silva et al. (2007 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

CH₆N₃⁺·C₄H₅O₆⁻·H₂O
M_r = 227.18
Triclinic, $[P \overline 1]$
a = 7.4588 (1) Å
b = 8.0931 (1) Å
c = 8.6423 (1) Å
α = 72.415 (1)°
β = 71.620 (1)°
γ = 81.558 (1)°
V = 471.18 (1) Å³
Z = 2
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 100 K
0.45 × 0.32 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.937, T_max = 0.979
10837 measured reflections
3418 independent reflections
3115 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.093
S = 1.02
3418 reflections
197 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O5ⁱ	0.82	1.72	2.5272 (10)	170
O3—H1O3⋯O6ⁱⁱ	0.836 (16)	1.832 (16)	2.6564 (9)	168.6 (16)
O4—H1O4⋯O1Wⁱⁱⁱ	0.852 (16)	1.963 (16)	2.7455 (10)	152.1 (15)
N1—H1N1⋯O1W^iv	0.845 (16)	2.184 (16)	3.0019 (11)	162.8 (15)
N1—H2N1⋯O6^iv	0.859 (16)	2.075 (16)	2.8573 (11)	151.2 (14)
N2—H1N2⋯O1	0.844 (16)	2.274 (16)	3.0131 (10)	146.3 (15)
N2—H2N2⋯O4^v	0.854 (15)	2.036 (15)	2.8828 (10)	170.7 (15)
N3—H1N3⋯O5^vi	0.862 (16)	2.049 (16)	2.8973 (11)	167.6 (15)
N3—H2N3⋯O1	0.847 (16)	2.441 (16)	3.1540 (11)	142.3 (14)
N3—H2N3⋯O3	0.847 (16)	2.345 (16)	3.0410 (11)	139.7 (14)
O1W—H1W1⋯O3ⁱⁱ	0.82 (2)	2.14 (2)	2.9051 (10)	155.0 (15)
O1W—H2W1⋯O1^vii	0.842 (16)	1.984 (16)	2.8100 (11)	166.4 (16)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1; (iii) x, y+1, z; (iv) x, y+1, z-1; (v) x, y, z-1; (vi) -x+1, -y+2, -z+1; (vii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037313/tk2542sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037313/tk2542Isup2.hkl

checkCIF report

Comment top

Guanidine, formed by the oxidation of guanine, is a strongly alkaline compound that can be used in the manufacturing of plastics and explosives. It is also the final product of the protein metabolism. Interest in this molecule spans many generations of chemists (Angyal & Warburton, 1951; Raczyńska et al., 2003; Yamada et al., 2009).

The asymmetric unit of the title salt (Fig. 1) contains a guanidinium cation, a 3-carboxy-2,3-dihydroxypropanoate anion and a water molecule. A proton transfer from the carboxyl group of 3-carboxy-2,3-dihydroxypropanoic acid to atom N1 of guanidine resulted in the formation of ions. The deprotonated carboxyl group is disordered over two positions with a site-occupancy ratio of 0.945 (3):0.055 (3). The C5—N1, C5—N2 and C5—N3 bond lengths in the propeller-shaped guanidinium cation (CN₃H₆)⁺ are almost equal [range of C—N = 1.3286 (10) – 1.3355 (10) Å], indicating that the usual model of electron dislocalization in this species (Allen et al., 1987). The bond lengths and angles are comparable to those found in closely related structures (Najafpour et al., 2007; Pereira Silva et al., 2007).

The crystal structure is mainly stabilized by a network of O—H···O and N—H···O hydrogen bonds. In this network, the O atoms of anion and water molecule act as donors as well as acceptors. Each guanidinium-H atom participates in intermolecular hydrogen bonds. In the crystal structure (Fig. 2), the anions and water molecules are linked into sheets parallel to the ab plane by intermolecular O2—H1O2···O5, O3—H1O3···O6, O4—H1O4···O1W, O1W—H1W1···O3 and O1W—H2W1···O1 hydrogen bonds (Table 1). The anions and water molecules are further linked with the cations by intermolecular N1—H1N1···O1W, N1—H2N1···O6, N2—H1N2···O1, N2—H2N2···O4, N3—H1N3···O5, N3—H2N3···O1 and N3—H2N3···O3 hydrogen bonds (Table 1), thus establishing a connection between these sheets to create a three-dimensional crystal structure.

Related literature top

For general background to and applications of guanidine derivatives, see: Angyal & Warburton (1951); Raczyńska et al. (2003); Yamada et al. (2009). For closely related guanidinium structures, see: Najafpour et al. (2007); Pereira Silva et al. (2007). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

Tartaric acid (1 mol) was dissolved in THF (10 ml) in a round bottom flask. In a separating funnel, guanidine carbonate (1 mol), 99 % [H₂NC(=NH)NH₂].2H₂CO₃, was dissolved in THF (10 ml) and three drops of concentrated HCl were added. The guanidine solution then was added drop-wise to the flask of tartaric acid with stirring. The reactant mixture was left stirring for 3 h at room temperature. The colourless single crystals formed were washed with THF and dried at 353 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme. Open bonds indicate the minor disordered component.
	Fig. 2. Unit cell contents of (I) viewed along the a axis, showing the three-dimensional network. Only the major component of the anion is shown. H atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

Guanidinium 3-carboxy-2,3-dihydroxypropanoate monohydrate top

Crystal data top

CH₆N₃⁺·C₄H₅O₆⁻·H₂O	Z = 2
M_r = 227.18	F(000) = 240
Triclinic, P1	D_x = 1.601 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4588 (1) Å	Cell parameters from 6392 reflections
b = 8.0931 (1) Å	θ = 2.6–32.6°
c = 8.6423 (1) Å	µ = 0.15 mm⁻¹
α = 72.415 (1)°	T = 100 K
β = 71.620 (1)°	Block, colourless
γ = 81.558 (1)°	0.45 × 0.32 × 0.14 mm
V = 471.18 (1) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3418 independent reflections
Radiation source: fine-focus sealed tube	3115 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 32.6°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
T_min = 0.937, T_max = 0.979	k = −11→12
10837 measured reflections	l = −12→13

Refinement top

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0471P)² + 0.1755P] where P = (F_o² + 2F_c²)/3
3418 reflections	(Δ/σ)_max < 0.001
197 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

CH₆N₃⁺·C₄H₅O₆⁻·H₂O	γ = 81.558 (1)°
M_r = 227.18	V = 471.18 (1) Å³
Triclinic, P1	Z = 2
a = 7.4588 (1) Å	Mo Kα radiation
b = 8.0931 (1) Å	µ = 0.15 mm⁻¹
c = 8.6423 (1) Å	T = 100 K
α = 72.415 (1)°	0.45 × 0.32 × 0.14 mm
β = 71.620 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3418 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3115 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.979	R_int = 0.018
10837 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.49 e Å⁻³
3418 reflections	Δρ_min = −0.27 e Å⁻³
197 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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 > 2sigma(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	Occ. (<1)
O1	−0.00986 (9)	0.73134 (10)	0.50517 (8)	0.02036 (14)
O2	−0.09291 (9)	0.54671 (9)	0.76558 (8)	0.01726 (13)
H1O2	−0.2005	0.5811	0.7604	0.026*
O3	0.35923 (9)	0.69520 (8)	0.49515 (8)	0.01562 (12)
O4	0.19600 (9)	0.77452 (8)	0.81295 (8)	0.01573 (12)
C1	0.02941 (11)	0.62976 (11)	0.62883 (10)	0.01333 (14)
C2	0.23376 (10)	0.58428 (10)	0.63385 (9)	0.01179 (13)
C3	0.25872 (11)	0.60619 (10)	0.79571 (9)	0.01189 (13)
C4	0.46665 (12)	0.55432 (14)	0.78966 (10)	0.01126 (17)	0.945 (3)
O5	0.57222 (9)	0.66863 (9)	0.77930 (9)	0.01673 (17)	0.945 (3)
O6	0.52211 (9)	0.39998 (9)	0.79084 (8)	0.01420 (16)	0.945 (3)
C4A	0.480 (3)	0.606 (3)	0.793 (2)	0.01126 (17)	0.055 (3)
O5A	0.503 (3)	0.736 (3)	0.823 (3)	0.042 (5)*	0.055 (3)
O6A	0.5654 (17)	0.4820 (18)	0.7605 (14)	0.015 (3)*	0.055 (3)
N1	0.29076 (11)	1.10920 (10)	−0.04338 (10)	0.01787 (14)
N2	0.13002 (11)	0.86542 (10)	0.12497 (9)	0.01554 (13)
N3	0.25830 (11)	1.02160 (10)	0.24365 (10)	0.01706 (14)
C5	0.22818 (11)	0.99832 (10)	0.10812 (10)	0.01293 (14)
O1W	0.31892 (10)	0.09289 (9)	0.60724 (9)	0.01863 (13)
H2A	0.2663 (17)	0.4572 (16)	0.6371 (16)	0.011 (3)*
H3A	0.1831 (18)	0.5272 (17)	0.8903 (17)	0.014 (3)*
H1O3	0.382 (2)	0.660 (2)	0.409 (2)	0.032 (4)*
H1O4	0.261 (2)	0.851 (2)	0.731 (2)	0.035 (4)*
H1N1	0.277 (2)	1.093 (2)	−0.131 (2)	0.029 (4)*
H2N1	0.356 (2)	1.194 (2)	−0.0562 (19)	0.024 (3)*
H1N2	0.112 (2)	0.789 (2)	0.219 (2)	0.029 (4)*
H2N2	0.136 (2)	0.8370 (19)	0.0359 (19)	0.023 (3)*
H1N3	0.325 (2)	1.105 (2)	0.233 (2)	0.026 (3)*
H2N3	0.227 (2)	0.944 (2)	0.337 (2)	0.025 (3)*
H1W1	0.417 (3)	0.143 (2)	0.551 (2)	0.039 (4)*
H2W1	0.240 (2)	0.154 (2)	0.559 (2)	0.036 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0161 (3)	0.0283 (3)	0.0131 (3)	0.0031 (2)	−0.0054 (2)	−0.0013 (2)
O2	0.0102 (2)	0.0224 (3)	0.0168 (3)	−0.0034 (2)	−0.0044 (2)	−0.0001 (2)
O3	0.0144 (3)	0.0197 (3)	0.0112 (2)	−0.0052 (2)	−0.00005 (19)	−0.0039 (2)
O4	0.0180 (3)	0.0138 (3)	0.0148 (3)	−0.0006 (2)	−0.0026 (2)	−0.0054 (2)
C1	0.0121 (3)	0.0160 (3)	0.0126 (3)	−0.0009 (2)	−0.0042 (2)	−0.0042 (3)
C2	0.0100 (3)	0.0140 (3)	0.0113 (3)	−0.0016 (2)	−0.0027 (2)	−0.0032 (2)
C3	0.0101 (3)	0.0138 (3)	0.0116 (3)	−0.0012 (2)	−0.0029 (2)	−0.0030 (2)
C4	0.0101 (3)	0.0143 (4)	0.0099 (3)	−0.0040 (3)	−0.0026 (2)	−0.0027 (3)
O5	0.0117 (3)	0.0165 (3)	0.0236 (3)	−0.0037 (2)	−0.0053 (2)	−0.0063 (2)
O6	0.0133 (3)	0.0135 (3)	0.0157 (3)	−0.0003 (2)	−0.0044 (2)	−0.0040 (2)
C4A	0.0101 (3)	0.0143 (4)	0.0099 (3)	−0.0040 (3)	−0.0026 (2)	−0.0027 (3)
N1	0.0182 (3)	0.0184 (3)	0.0147 (3)	−0.0050 (3)	−0.0037 (2)	−0.0003 (3)
N2	0.0188 (3)	0.0143 (3)	0.0139 (3)	−0.0032 (2)	−0.0050 (2)	−0.0030 (2)
N3	0.0212 (3)	0.0164 (3)	0.0156 (3)	−0.0027 (3)	−0.0073 (3)	−0.0043 (3)
C5	0.0112 (3)	0.0133 (3)	0.0136 (3)	0.0011 (2)	−0.0034 (2)	−0.0036 (2)
O1W	0.0148 (3)	0.0186 (3)	0.0192 (3)	−0.0026 (2)	−0.0058 (2)	0.0013 (2)

Geometric parameters (Å, º) top

O1—C1	1.2246 (10)	C4—O5	1.2662 (12)
O2—C1	1.3042 (10)	C4A—O6A	1.17 (2)
O2—H1O2	0.8200	C4A—O5A	1.20 (3)
O3—C2	1.4169 (9)	N1—C5	1.3286 (10)
O3—H1O3	0.840 (18)	N1—H1N1	0.844 (17)
O4—C3	1.4101 (10)	N1—H2N1	0.859 (15)
O4—H1O4	0.851 (18)	N2—C5	1.3355 (10)
C1—C2	1.5258 (11)	N2—H1N2	0.846 (16)
C2—C3	1.5319 (11)	N2—H2N2	0.854 (16)
C2—H2A	1.015 (13)	N3—C5	1.3303 (10)
C3—C4	1.5347 (11)	N3—H1N3	0.865 (16)
C3—C4A	1.641 (18)	N3—H2N3	0.851 (15)
C3—H3A	0.945 (13)	O1W—H1W1	0.822 (19)
C4—O6	1.2549 (12)	O1W—H2W1	0.842 (18)

C1—O2—H1O2	109.5	C4A—C3—H3A	115.5 (10)
C2—O3—H1O3	109.6 (11)	O6—C4—O5	124.13 (8)
C3—O4—H1O4	110.8 (12)	O6—C4—C3	116.93 (8)
O1—C1—O2	125.21 (8)	O5—C4—C3	118.92 (8)
O1—C1—C2	121.76 (7)	O6A—C4A—O5A	140 (2)
O2—C1—C2	113.01 (7)	O6A—C4A—C3	110.4 (14)
O3—C2—C1	111.04 (6)	O5A—C4A—C3	109.7 (16)
O3—C2—C3	107.06 (6)	C5—N1—H1N1	121.2 (11)
C1—C2—C3	110.81 (6)	C5—N1—H2N1	120.5 (10)
O3—C2—H2A	112.1 (7)	H1N1—N1—H2N1	118.0 (14)
C1—C2—H2A	109.1 (7)	C5—N2—H1N2	115.7 (11)
C3—C2—H2A	106.6 (7)	C5—N2—H2N2	118.2 (10)
O4—C3—C2	111.00 (6)	H1N2—N2—H2N2	119.5 (14)
O4—C3—C4	115.34 (7)	C5—N3—H1N3	120.5 (10)
C2—C3—C4	106.58 (6)	C5—N3—H2N3	118.7 (10)
O4—C3—C4A	99.2 (7)	H1N3—N3—H2N3	119.9 (15)
C2—C3—C4A	114.6 (6)	N1—C5—N3	120.41 (8)
C4—C3—C4A	16.1 (7)	N1—C5—N2	119.70 (7)
O4—C3—H3A	107.2 (8)	N3—C5—N2	119.87 (7)
C2—C3—H3A	108.8 (8)	H1W1—O1W—H2W1	101.2 (17)
C4—C3—H3A	107.8 (8)

O1—C1—C2—O3	10.22 (11)	C2—C3—C4—O6	−62.98 (9)
O2—C1—C2—O3	−171.38 (7)	C4A—C3—C4—O6	175 (2)
O1—C1—C2—C3	129.07 (8)	O4—C3—C4—O5	−8.52 (11)
O2—C1—C2—C3	−52.53 (9)	C2—C3—C4—O5	115.16 (8)
O3—C2—C3—O4	66.54 (8)	C4A—C3—C4—O5	−7 (2)
C1—C2—C3—O4	−54.69 (8)	O4—C3—C4A—O6A	−172.1 (12)
O3—C2—C3—C4	−59.80 (8)	C2—C3—C4A—O6A	−53.8 (14)
C1—C2—C3—C4	178.98 (7)	C4—C3—C4A—O6A	9.2 (12)
O3—C2—C3—C4A	−44.8 (7)	O4—C3—C4A—O5A	6.8 (16)
C1—C2—C3—C4A	−166.1 (7)	C2—C3—C4A—O5A	125.0 (14)
O4—C3—C4—O6	173.34 (7)	C4—C3—C4A—O5A	−172 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O5ⁱ	0.82	1.72	2.5272 (10)	170
O3—H1O3···O6ⁱⁱ	0.836 (16)	1.832 (16)	2.6564 (9)	168.6 (16)
O4—H1O4···O1Wⁱⁱⁱ	0.852 (16)	1.963 (16)	2.7455 (10)	152.1 (15)
N1—H1N1···O1W^iv	0.845 (16)	2.184 (16)	3.0019 (11)	162.8 (15)
N1—H2N1···O6^iv	0.859 (16)	2.075 (16)	2.8573 (11)	151.2 (14)
N2—H1N2···O1	0.844 (16)	2.274 (16)	3.0131 (10)	146.3 (15)
N2—H2N2···O4^v	0.854 (15)	2.036 (15)	2.8828 (10)	170.7 (15)
N3—H1N3···O5^vi	0.862 (16)	2.049 (16)	2.8973 (11)	167.6 (15)
N3—H2N3···O1	0.847 (16)	2.441 (16)	3.1540 (11)	142.3 (14)
N3—H2N3···O3	0.847 (16)	2.345 (16)	3.0410 (11)	139.7 (14)
O1W—H1W1···O3ⁱⁱ	0.82 (2)	2.14 (2)	2.9051 (10)	155.0 (15)
O1W—H2W1···O1^vii	0.842 (16)	1.984 (16)	2.8100 (11)	166.4 (16)

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

Experimental details

Crystal data
Chemical formula	CH₆N₃⁺·C₄H₅O₆⁻·H₂O
M_r	227.18
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.4588 (1), 8.0931 (1), 8.6423 (1)
α, β, γ (°)	72.415 (1), 71.620 (1), 81.558 (1)
V (Å³)	471.18 (1)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.45 × 0.32 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.937, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	10837, 3418, 3115
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.093, 1.02
No. of reflections	3418
No. of parameters	197
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.27

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O5ⁱ	0.8200	1.7200	2.5272 (10)	170.00
O3—H1O3···O6ⁱⁱ	0.836 (16)	1.832 (16)	2.6564 (9)	168.6 (16)
O4—H1O4···O1Wⁱⁱⁱ	0.852 (16)	1.963 (16)	2.7455 (10)	152.1 (15)
N1—H1N1···O1W^iv	0.845 (16)	2.184 (16)	3.0019 (11)	162.8 (15)
N1—H2N1···O6^iv	0.859 (16)	2.075 (16)	2.8573 (11)	151.2 (14)
N2—H1N2···O1	0.844 (16)	2.274 (16)	3.0131 (10)	146.3 (15)
N2—H2N2···O4^v	0.854 (15)	2.036 (15)	2.8828 (10)	170.7 (15)
N3—H1N3···O5^vi	0.862 (16)	2.049 (16)	2.8973 (11)	167.6 (15)
N3—H2N3···O1	0.847 (16)	2.441 (16)	3.1540 (11)	142.3 (14)
N3—H2N3···O3	0.847 (16)	2.345 (16)	3.0410 (11)	139.7 (14)
O1W—H1W1···O3ⁱⁱ	0.82 (2)	2.14 (2)	2.9051 (10)	155.0 (15)
O1W—H2W1···O1^vii	0.842 (16)	1.984 (16)	2.8100 (11)	166.4 (16)

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

This research was supported by Universiti Sains Malaysia (USM) under a Short Term Grant (No. 304/PKIMIA/639039). HKF and JHG thank USM for a Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

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