Potassium 2-(N-hydroxy-carbamo-yl)acetate monohydrate.

The crystal structure of the title compound, K(+)·C(3)H(4)NO(4) (-)·H(2)O, consists of potassium cations, monoanions of 2-carboxy-acetohydroxamic acid [namely 2-(N-hydroxy-carbamo-yl)acetate] and solvent water mol-ecules. The elements of the structure are united in a three-dimensional network by numerous K⋯O coordinate bonds and O-H⋯O and N-H⋯O hydrogen bonds. The coordination sphere of the K(+) ions may be described as a distorted double capped octa-hedron. Bond lengths and angles are similar to those in related compounds.

Related literature

For background to hydroxamic acids in biological and coordination chemistry, see: Kaczka et al. (1962 ▶); Hershko et al. (1992 ▶); Ghio et al. (1992 ▶); Shao et al. (2004 ▶). For hydroxamic acids as versatile bridging ligands, see: Bodwin et al. (2001 ▶); Cutland-Van Noord et al. (2002 ▶). For related structures, see: Golenya et al. (2007 ▶); Gumienna-Kontecka et al. (2007 ▶); Wörl et al. (2005 ▶). For K—O bond lengths, see: Świątek-Kozłowska et al. (2000 ▶); Mokhir et al. (2002 ▶).

Experimental

Crystal data

K+·C3H4NO4 −·H2O

M = 175.19

Monoclinic,

a = 7.457 (1) Å

b = 13.002 (3) Å

c = 6.816 (1) Å

β = 105.41 (3)°

V = 637.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.80 mm−1

T = 100 K

0.25 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.829, T max = 0.914

3974 measured reflections

1498 independent reflections

1398 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.064

S = 1.10

1498 reflections

107 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809038434/bv2123sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038434/bv2123Isup2.hkl

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

K+·C3H4NO4−·H2O	F(000) = 360
Mr = 175.19	Dx = 1.826 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 567 reflections
a = 7.457 (1) Å	θ = 3.5–27.5°
b = 13.002 (3) Å	µ = 0.80 mm−1
c = 6.816 (1) Å	T = 100 K
β = 105.41 (3)°	Needle, colourless
V = 637.1 (2) Å3	0.25 × 0.20 × 0.12 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1498 independent reflections
Radiation source: fine-focus sealed tube	1398 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 28.4°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −9→9
Tmin = 0.829, Tmax = 0.914	k = −17→17
3974 measured reflections	l = −6→9

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0348P)2 + 0.2753P] where P = (Fo2 + 2Fc2)/3
1498 reflections	(Δ/σ)max < 0.001
107 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

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
K1	0.50362 (4)	0.64050 (2)	0.09788 (4)	0.01167 (10)
O1	−0.30644 (12)	0.82467 (7)	0.01504 (14)	0.0127 (2)
O2	−0.09437 (12)	0.92917 (7)	0.20776 (13)	0.01173 (19)
O3	0.27158 (12)	0.76799 (7)	0.24610 (13)	0.01273 (19)
O4	0.46616 (12)	0.93401 (7)	0.18090 (13)	0.0122 (2)
O1W	0.77186 (13)	0.51272 (8)	0.03917 (15)	0.0155 (2)
N1	0.28881 (15)	0.90970 (9)	0.06042 (16)	0.0110 (2)
C1	−0.14337 (17)	0.85843 (9)	0.07756 (18)	0.0091 (2)
C2	0.00201 (17)	0.81466 (10)	−0.02077 (18)	0.0112 (2)
H2A	−0.0220	0.7419	−0.0464	0.013*
H2B	−0.0110	0.8482	−0.1510	0.013*
C3	0.19948 (16)	0.82835 (10)	0.10799 (18)	0.0096 (2)
H4O	0.543 (3)	0.8999 (18)	0.124 (3)	0.031 (5)*
H1N	0.243 (3)	0.9497 (15)	−0.027 (3)	0.024 (5)*
H1W	0.863 (3)	0.4904 (18)	0.125 (3)	0.036 (6)*
H2W	0.807 (3)	0.5327 (18)	−0.062 (4)	0.043 (6)*

	U11	U22	U33	U12	U13	U23
K1	0.01153 (15)	0.01230 (16)	0.01062 (15)	0.00162 (9)	0.00197 (10)	−0.00076 (9)
O1	0.0095 (4)	0.0153 (4)	0.0134 (4)	−0.0009 (3)	0.0029 (3)	−0.0024 (3)
O2	0.0112 (4)	0.0130 (4)	0.0108 (4)	0.0004 (3)	0.0024 (3)	−0.0031 (3)
O3	0.0131 (4)	0.0140 (4)	0.0112 (4)	0.0013 (3)	0.0034 (3)	0.0021 (3)
O4	0.0078 (4)	0.0165 (5)	0.0118 (4)	−0.0021 (3)	0.0020 (3)	−0.0035 (3)
O1W	0.0120 (4)	0.0218 (5)	0.0130 (5)	0.0038 (4)	0.0041 (4)	0.0064 (4)
N1	0.0096 (5)	0.0121 (5)	0.0097 (5)	0.0001 (4)	−0.0002 (4)	0.0006 (4)
C1	0.0103 (5)	0.0096 (6)	0.0070 (5)	0.0016 (4)	0.0018 (4)	0.0026 (4)
C2	0.0104 (5)	0.0133 (6)	0.0099 (5)	−0.0001 (4)	0.0031 (4)	−0.0029 (4)
C3	0.0096 (5)	0.0113 (6)	0.0092 (5)	0.0009 (4)	0.0047 (4)	−0.0028 (4)

K1—O1W	2.7105 (11)	O4—N1	1.3951 (14)
K1—O3	2.7734 (10)	O4—H4O	0.89 (2)
K1—O3i	2.8202 (12)	O1W—H1W	0.82 (2)
K1—O1Wii	2.8358 (12)	O1W—H2W	0.84 (3)
K1—O1iii	2.8558 (12)	N1—C3	1.3351 (17)
K1—O1iv	2.9128 (11)	N1—H1N	0.79 (2)
K1—O4i	2.9448 (10)	C1—C2	1.5279 (17)
K1—O4v	3.0580 (11)	C2—C3	1.5111 (17)
O1—C1	1.2560 (15)	C2—H2A	0.9700
O2—C1	1.2628 (15)	C2—H2B	0.9700
O3—C3	1.2337 (16)
O1W—K1—O3	167.55 (3)	O3i—K1—O4v	137.54 (3)
O1W—K1—O3i	116.31 (3)	O1Wii—K1—O4v	59.85 (3)
O3—K1—O3i	75.90 (2)	O1iii—K1—O4v	72.32 (3)
O1W—K1—O1Wii	91.10 (3)	O1iv—K1—O4v	147.29 (3)
O3—K1—O1Wii	94.15 (3)	O4i—K1—O4v	99.36 (3)
O3i—K1—O1Wii	77.83 (4)	N1—O4—H4O	104.5 (13)
O1W—K1—O1iii	93.09 (4)	H1W—O1W—H2W	108 (2)
O3—K1—O1iii	74.63 (3)	C3—N1—O4	119.52 (10)
O3i—K1—O1iii	144.05 (3)	C3—N1—H1N	124.0 (14)
O1Wii—K1—O1iii	124.30 (3)	O4—N1—H1N	116.1 (14)
O1W—K1—O1iv	93.40 (3)	O1—C1—O2	124.49 (11)
O3—K1—O1iv	87.81 (3)	O1—C1—C2	117.18 (11)
O3i—K1—O1iv	73.05 (3)	O2—C1—C2	118.23 (11)
O1Wii—K1—O1iv	149.40 (3)	C3—C2—C1	113.38 (10)
O1iii—K1—O1iv	85.67 (3)	C3—C2—H2A	108.9
O1W—K1—O4i	62.64 (4)	C1—C2—H2A	108.9
O3—K1—O4i	129.78 (3)	C3—C2—H2B	108.9
O3i—K1—O4i	55.86 (3)	C1—C2—H2B	108.9
O1Wii—K1—O4i	64.93 (3)	H2A—C2—H2B	107.7
O1iii—K1—O4i	155.21 (3)	O3—C3—N1	123.01 (11)
O1iv—K1—O4i	90.56 (3)	O3—C3—C2	121.88 (11)
O1W—K1—O4v	64.79 (3)	N1—C3—C2	115.11 (11)
O3—K1—O4v	108.45 (3)
O1—C1—C2—C3	−159.16 (11)	O4—N1—C3—C2	174.68 (10)
O2—C1—C2—C3	24.31 (15)	C1—C2—C3—O3	83.28 (14)
O4—N1—C3—O3	−5.58 (18)	C1—C2—C3—N1	−96.98 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O1iv	0.89 (2)	1.79 (2)	2.6820 (13)	177 (2)
N1—H1N···O2vi	0.79 (2)	2.12 (2)	2.9025 (16)	166.7 (18)
O1W—H1W···O2v	0.82 (2)	1.97 (2)	2.7811 (15)	171 (2)
O1W—H2W···O2vii	0.84 (3)	1.97 (3)	2.8046 (14)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O1i	0.89 (2)	1.79 (2)	2.6820 (13)	177 (2)
N1—H1N⋯O2ii	0.79 (2)	2.12 (2)	2.9025 (16)	166.7 (18)
O1W—H1W⋯O2iii	0.82 (2)	1.97 (2)	2.7811 (15)	171 (2)
O1W—H2W⋯O2iv	0.84 (3)	1.97 (3)	2.8046 (14)	175 (2)

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