Guanidinium 3-carb-oxy-2,3-dihydroxy-propanoate monohydrate.

In the title hydrated salt, CH(6)N(3) (+)·C(4)H(5)O(6) (-)·H(2)O, 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 inter-mediate between normal C-N and C=N bond lengths, indicating significant delocalization in this species. In the crystal structure, anions and water mol-ecules are linked into sheets parallel to the ab plane by inter-molecular O-H⋯O hydrogen bonds. The linking of the anions and water mol-ecules with the cations by inter-molecular 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 = 227.18

Triclinic,

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 (; 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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.02

3418 reflections

197 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.27 e Å−3

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 ▶).

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

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

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

CH6N3+·C4H5O6−·H2O	Z = 2
Mr = 227.18	F(000) = 240
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0471P)2 + 0.1755P] where P = (Fo2 + 2Fc2)/3
3418 reflections	(Δ/σ)max < 0.001
197 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)*

	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)

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)

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···O1Wiv	0.845 (16)	2.184 (16)	3.0019 (11)	162.8 (15)
N1—H2N1···O6iv	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···O4v	0.854 (15)	2.036 (15)	2.8828 (10)	170.7 (15)
N3—H1N3···O5vi	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···O1vii	0.842 (16)	1.984 (16)	2.8100 (11)	166.4 (16)

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⋯O1Wiv	0.845 (16)	2.184 (16)	3.0019 (11)	162.8 (15)
N1—H2N1⋯O6iv	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⋯O4v	0.854 (15)	2.036 (15)	2.8828 (10)	170.7 (15)
N3—H1N3⋯O5vi	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⋯O1vii	0.842 (16)	1.984 (16)	2.8100 (11)	166.4 (16)

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