Potassium 2-(N-hydroxy­carbamo­yl)acetate monohydrate

Prisyazhnaya, E.V.; Odarich, I.; Fritsky, I.O.; Gumienna-Kontecka, E.; Iskenderov, T.S.

doi:10.1107/S1600536809038434

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages m1254-m1255

doi:10.1107/S1600536809038434

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Potassium 2-(N-hydroxycarbamoyl)acetate monohydrate

Elena V. Prisyazhnaya,^a Irina Odarich,^b Igor O. Fritsky,^c Elżbieta Gumienna-Kontecka ^d and Turganbay S. Iskenderov ^e ^*

^aKyiv National University of Construction and Architecture, Department of Chemistry, Povitroflotsky Ave., 31, 03680 Kiev, Ukraine, ^bNational Medical University, Department of General Chemistry, Volodymyrska str. 13, 010004 Kiev, Ukraine, ^cNational Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01033 Kiev, Ukraine, ^dFaculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie str., 50-383 Wrocław, Poland, and ^eKarakalpakian University, Department of Chemistry, Universitet Keshesi 1, 742012 Nukus, Uzbekistan
^*Correspondence e-mail: turgiskend@freemail.ru

(Received 19 July 2009; accepted 22 September 2009; online 30 September 2009)

The crystal structure of the title compound, K⁺·C₃H₄NO₄⁻·H₂O, consists of potassium cations, monoanions of 2-carboxyacetohydroxamic acid [namely 2-(N-hydroxycarbamoyl)acetate] and solvent water molecules. 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 octahedron. 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_r = 175.19
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.025
wR(F²) = 0.064
S = 1.10
1498 reflections
107 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.43 e Å⁻³

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⋯O2^iv	0.84 (3)	1.97 (3)	2.8046 (14)	175 (2)
Symmetry codes: (i) x+1, y, z; (ii) -x, -y+2, -z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Hydroxamic acids represent an important class of chelating agents and enzyme inhibitors (Kaczka et al., 1962; Hershko et al., 1992; Ghio et al., 1992; Shao et al., 2004). In recent years hydroxamic acids have also been widely used in coordination chemistry as versatile bridging ligands able to produce multinuclear compounds containing a large number of metal ions, such as metallacrowns (Bodwin et al., 2001; Cutland-Van Noord et al., 2002). Recently we reported that 2-carboxyacetohydroxamic acid is an efficient ligand for obtaining 12-metallacrown-4 complexes with copper(II) ions which can be used as pentanuclear building blocks for preparation of one-dimensional coordination polymers (Gumienna-Kontecka et al., 2007). The present investigation is aimed at the study of the molecular structure of the title compound (I) which is a suitable ligand for preparation of polynuclear complexes and coordination polymers.

The atom-numbering scheme of compound (I) is shown in Fig. 1. The crystal structure of (I) is ionic and consists of potassium cations, monoanions of 2-carboxyacetohydroxamic acid and solvate water molecules. The elements of the structure are united in three-dimensional-network by numerous K···O coordination bonds and the O—H···O and N—H···O hydrogen bonds (Fig. 2,. Table 1).

The residue of 2-carboxyacetohydroxamic acid is a monoanion bearing the deprotonated carboxylic group with the hydroxamic function remaining protonated. The anion exhibits C—O, N—O, C—N bond lengths which are typical for carboxylic and hydroxamic groups (Wörl et al., 2005, Golenya et al., 2007). The conformation of monoanion of 2-carboxyacetohydroxamic acid is significantly non-planar due to the presence of the flexible C—CH₂—C moiety uniting two planar hydroxamic and carboxylic fragments. The mentioned groups are disposed nearly perpendicularly; the dihedral angle between their planes is equal to 86.37 (5)^o.

The potassium cation exhibits coordination number 8, and its coordination polyhedron can be considered as severely distorted double capped octahedron. Its coordination environment is formed by two solvate water molecules and six oxygen atoms of monoanion of 2-carboxyacetohydroxamic acid belonging to the deprotonated carboxylic groups (O(1)) and both oxygen atoms of the hydroxamic functions(O(3) and O(4)) belonging to the different translational anions. Each potassium cation has in its coordination sphere the oxygen atoms belonging to five different translational monoanions of 2-carboxyacetohydroxamic acid. The K—O bond lengths lie in the range 2.711 (1) - 3.058 (1) Å which is normal for potassium cations (Świątek-Kozłowska et al., 2000; Mokhir et al., 2002).

Related literature top

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 top

I was obtained as white powder precipitate by addition of 1 equiv. of KOH (1 M aqueous solution) to warm solution of 2-carboxyacetohydroxamic acid (1.19 g, 10 mmol) in water (40 ml) with consequent reduction in volume of the obtained solution. Single crystals suitable for X-ray analysis were grown by slow isothermal evaporation of aqueous solution at room temperature. Anal. For C₃H₆NO₅K (175.18) calcd.: C - 20.57, H - 3.45, N - 8.00. Found: C - 20.7, H - 3.5, N - 7.8. - IR (cm^-1): 1062 (ν(N—O)), 1380 (ν_s(COO^-)), 1580 (ν_as(COO^-)), 1672 (ν(C=O) Amide I).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of compound (I), with displacement ellipsoids shown at the 50% probability level. H atoms are drawn as spheres of arbitrary radii. The hydrogen bonding is shown by dashed lines [symmetry codes: (i) 1 + x, y, z; (ii) x, 1.5 - y, -1/2 + z; (iii) 1 + x, 1.5 - y, 1/2 + z; (iv)1 - x, 1 - y, - z; (v) 1 - x, -1/2 + y, 1/2 - z].
	Fig. 2. A packing diagram of the title compound. Hydrogen bonds are indicated by dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

Potassium 2-(N-hydroxycarbamoyl)acetate monohydrate top

Crystal data top

K⁺·C₃H₄NO₄⁻·H₂O	F(000) = 360
M_r = 175.19	D_x = 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

Data collection top

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

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)] = 0.025	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(F_o²) + (0.0348P)² + 0.2753P] where P = (F_o² + 2F_c²)/3
1498 reflections	(Δ/σ)_max < 0.001
107 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

K⁺·C₃H₄NO₄⁻·H₂O	V = 637.1 (2) Å³
M_r = 175.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.457 (1) Å	µ = 0.80 mm⁻¹
b = 13.002 (3) Å	T = 100 K
c = 6.816 (1) Å	0.25 × 0.20 × 0.12 mm
β = 105.41 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1498 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	1398 reflections with I > 2σ(I)
T_min = 0.829, T_max = 0.914	R_int = 0.025
3974 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.36 e Å⁻³
1498 reflections	Δρ_min = −0.43 e Å⁻³
107 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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—O1^iv	2.9128 (11)	N1—H1N	0.79 (2)
K1—O4ⁱ	2.9448 (10)	C1—C2	1.5279 (17)
K1—O4^v	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—O4^v	137.54 (3)
O1W—K1—O3ⁱ	116.31 (3)	O1Wⁱⁱ—K1—O4^v	59.85 (3)
O3—K1—O3ⁱ	75.90 (2)	O1ⁱⁱⁱ—K1—O4^v	72.32 (3)
O1W—K1—O1Wⁱⁱ	91.10 (3)	O1^iv—K1—O4^v	147.29 (3)
O3—K1—O1Wⁱⁱ	94.15 (3)	O4ⁱ—K1—O4^v	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—O1^iv	93.40 (3)	O1—C1—O2	124.49 (11)
O3—K1—O1^iv	87.81 (3)	O1—C1—C2	117.18 (11)
O3ⁱ—K1—O1^iv	73.05 (3)	O2—C1—C2	118.23 (11)
O1Wⁱⁱ—K1—O1^iv	149.40 (3)	C3—C2—C1	113.38 (10)
O1ⁱⁱⁱ—K1—O1^iv	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)
O1^iv—K1—O4ⁱ	90.56 (3)	O3—C3—C2	121.88 (11)
O1W—K1—O4^v	64.79 (3)	N1—C3—C2	115.11 (11)
O3—K1—O4^v	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)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z; (iii) x+1, −y+3/2, z+1/2; (iv) x+1, y, z; (v) −x+1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O1^iv	0.89 (2)	1.79 (2)	2.6820 (13)	177 (2)
N1—H1N···O2^vi	0.79 (2)	2.12 (2)	2.9025 (16)	166.7 (18)
O1W—H1W···O2^v	0.82 (2)	1.97 (2)	2.7811 (15)	171 (2)
O1W—H2W···O2^vii	0.84 (3)	1.97 (3)	2.8046 (14)	175 (2)

Symmetry codes: (iv) x+1, y, z; (v) −x+1, y−1/2, −z+1/2; (vi) −x, −y+2, −z; (vii) x+1, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	K⁺·C₃H₄NO₄⁻·H₂O
M_r	175.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.457 (1), 13.002 (3), 6.816 (1)
β (°)	105.41 (3)
V (Å³)	637.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.25 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.829, 0.914
No. of measured, independent and observed [I > 2σ(I)] reflections	3974, 1498, 1398
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.064, 1.10
No. of reflections	1498
No. of parameters	107
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.43

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.84 (3)	1.97 (3)	2.8046 (14)	175 (2)

Symmetry codes: (i) x+1, y, z; (ii) −x, −y+2, −z; (iii) −x+1, y−1/2, −z+1/2; (iv) x+1, −y+3/2, z−1/2.

Acknowledgements

The authors thank the Ministry of Education and Science of Ukraine for financial support (grant No. M/42–2008).

References

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