N-(2-Hydroxy­ethyl)-2-[2-(hydroxy­imino)propanamido]ethanaminium 2-(hydroxy­imino)propanoate

Iskenderov, T.S.; Kalibabchuk, V.A.; Golenya, I.A.; Dudarenko, N.M.; Usenko, N.I.

doi:10.1107/S1600536809029778

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages o2077-o2078

doi:10.1107/S1600536809029778

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N-(2-Hydroxyethyl)-2-[2-(hydroxyimino)propanamido]ethanaminium 2-(hydroxyimino)propanoate

Turganbay S. Iskenderov,^a ^* Valentina A. Kalibabchuk,^b Irina A. Golenya,^c Nikolay M. Dudarenko ^c and Natalia I. Usenko ^c

^aKarakalpakian University, Department of Chemistry, Universitet Keshesi 1, 742012 Nukus, Uzbekistan, ^bO. O. Bohomolets National Medical University, Department of General Chemistry, Shevchenko Blvd. 13, 01601 Kiev, Ukraine, and ^cKiev National Taras Shevchenko University, Department of Chemistry, Volodymyrska Str. 64, 01601 Kiev, Ukraine
^*Correspondence e-mail: turgiskend@freemail.ru

(Received 21 July 2009; accepted 27 July 2009; online 8 August 2009)

The cation of the title salt, C₇H₁₆N₃O₃⁺·C₃H₄NO₃⁻, the oxime group is trans with respect to the amide–carbonyl group. The components of the structure are united into a three-dimensional network by an extensive system of O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For background to oximes in coordination chemistry, see: Kukushkin et al. (1996 ); Chaudhuri (2003 ). For polynuclear species arising from bridging and/or functionalized oximes, see: Cervera et al. (1997 ); Costes et al. (1998 ); Moroz et al. (2008 ); Onindo et al. (1995 ); Sliva et al. (1997a ,b ); Gumienna-Kontecka et al. (2000 ). For oximes stabilizing high oxidation states, see: Kanderal et al. (2005 ); Fritsky et al. (2006 ). For related structures, see: Duda et al. (1997 ); Fritsky et al. (1999 ); Fritsky (1999 ); Mokhir et al. (2002 ). For the synthesis, see: Lau & Gutsche (1978 ).

Experimental

Crystal data

C₇H₁₆N₃O₃⁺·C₃H₄NO₃⁻
M_r = 292.30
Monoclinic, P 2₁ /c
a = 9.355 (2) Å
b = 6.996 (1) Å
c = 20.606 (4) Å
β = 96.99 (3)°
V = 1338.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 120 K
0.30 × 0.24 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (North et al., 1968 ) T_min = 0.957, T_max = 0.979
8410 measured reflections
3090 independent reflections
1887 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.088
S = 0.92
3090 reflections
201 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 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
O3—H3O⋯O5ⁱ	0.90 (2)	1.78 (2)	2.677 (2)	173 (2)
O4—H4O⋯O2ⁱⁱ	0.95 (2)	1.63 (2)	2.5733 (18)	172.3 (19)
O6—H6O⋯O2	0.87 (2)	2.25 (2)	3.101 (2)	163.4 (18)
N3—H3N⋯O6ⁱⁱ	0.86 (2)	2.11 (2)	2.940 (2)	162.6 (18)
N4—H4N⋯O1ⁱⁱⁱ	0.970 (19)	1.93 (2)	2.838 (2)	155.1 (15)
N4—H5N⋯O1^iv	0.895 (18)	1.921 (19)	2.796 (2)	165.1 (17)
Symmetry codes: (i) $[-x-1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x, -y, -z+2; (iii) x+1, y, z; (iv) -x-1, -y, -z+2.

Data collection: COLLECT (Bruker, 2004 ); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029778/tk2512sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029778/tk2512Isup2.hkl

checkCIF report

Comment top

Oximes are classical type of chelating ligands traditionally widely used in coordination and analytical chemistry (Kukushkin et al., 1996; Chaudhuri, 2003). They are also important bridging ligands extensively used in molecular magnetism for obtaining of polynuclear complexes (Cervera et al., 1997; Costes et al., 1998; Moroz et al., 2008). The presence of an additional donor function in the vicinity to the oxime group may result in important increase of chelating efficiency and ability to form polynuclear species. For example, amide derivatives of 2-hydroxyiminopropanoic acid were shown to act as highly efficient chelators with respect to Cu(II), Ni(II) and Al(III) (Onindo et al., 1995; Sliva et al., 1997a; Sliva, et al., 1997b; Gumienna-Kontecka et al., 2000). Recently, owing to their strong σ-donor capacity, open-chain tetradentate oxime and amide ligands were shown to efficiently stabilize unusual oxidation states of metal ions, such as Cu³⁺ and Ni³⁺ (Kanderal et al., 2005; Fritsky et al., 2006). The present investigation is dedicated to the study of the molecular structure of the title compound (I), which is a new polynucleative ligand containing several donor functions: oxime, amine, amide and alcohol.

The structure of (I) is ionic and and comprises cations of N-[2-(2-hydroxy-ethylammonium)ethyl]-2-hydroxyiminopropanamide and 2-(hydroxyimino)propanoate anions (Fig. 1). The cation has a Γ-shaped conformation and consists of two nearly planar CH₃C(=NOH)C(O)NHCH₂and CH₂CH₂NH₂CH₂ fragments. The dihedral plane between their mean planes, defined by the non-hydrogen atoms, is 75.8 (1)°. The hydroxyl group is situated nearly perpendicular to the CH₂CH₂NH₂CH₂ moiety: the torsion angle N4/C9/C10/O6 is 60.2 (2)°. The observed conformation of the CH₃C(=NOH)C(O)NHCH₂moiety is the same as that observed in the structure of N,N'-bis(2-hydroxyiminopropionylpropane)-1,2-diamine and its homologues (Duda et al., 1997; Fritsky, Karaczyn et al., 1999). The oxime group is trans to the amide-carbonyl. It is noted that the CH₃C(=NOH)C(O)NHCH₂moiety deviates somewhat from planarity because of a twisting of the oxime and amide groups along the C5—C6 bond. The dihedral angle between the corresponding least square planes is 9.5 (1)°. The C=N, C=O, N—O, C—N bond lengths are typical for 2-hydroxyiminopropanoic acid and its amide derivatives (Duda et al., 1997; Fritsky, 1999; Mokhir et al., 2002).

The elements of the structure are united into a 3-D network by extensive system of the O—H···O and N—H···O hydrogen bonds (Table 1).

Related literature top

For background to oximes in coordination chemistry, see: Kukushkin et al. (1996); Chaudhuri (2003). For polynuclear species arising from bridging and/or functionalized oximes, see: Cervera et al. (1997); Costes et al. (1998); Moroz et al. (2008); Onindo et al. (1995); Sliva et al. (1997a,b); Gumienna-Kontecka et al. (2000). For oximes stabilizing high oxidation states, see: Kanderal et al. (2005); Fritsky et al. (2006). For related structures, see: Duda et al. (1997); Fritsky et al. (1999); Fritsky (1999); Mokhir et al. (2002). For the synthesis, see: Lau & Gutsche (1978).

Experimental top

Ethyl 2-(hydroxyimino)propanoate (1.31 g, 0.01 mol) was dissolved in methanol (50 ml) to which 2-((2-aminoethyl)amino)ethanol (1.04 g, 0.01 mol) was added. The mixture was set aside for 24 h at room temperature, then the solvent was removed on a rotary evaporator. Recrystallization of the crude product from water afforded the pure (I) in the form of single crystals. Ethyl 2-(hydroxyimino)propanoate was prepared according to the reported method (Lau & Gutsche, 1978).

Computing details top

Data collection: COLLECT (Bruker, 2004); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); 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. Hydrogen bonds are indicated by dashed lines.

N-(2-Hydroxyethyl)-2-[2-(hydroxyimino)propanamido]ethanaminium 2-(hydroxyimino)propanoate top

Crystal data top

C₇H₁₆N₃O₃⁺·C₃H₄NO₃⁻	F(000) = 624
M_r = 292.30	D_x = 1.450 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1078 reflections
a = 9.355 (2) Å	θ = 3.2–27.5°
b = 6.996 (1) Å	µ = 0.12 mm⁻¹
c = 20.606 (4) Å	T = 120 K
β = 96.99 (3)°	Block, colourless
V = 1338.6 (4) Å³	0.30 × 0.24 × 0.20 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	3090 independent reflections
Radiation source: fine-focus sealed tube	1887 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	R_int = 0.049
Detector resolution: 9 pixels mm^-1	θ_max = 28.4°, θ_min = 3.1°
ϕ scans and ω scans with κ offset	h = −12→9
Absorption correction: multi-scan (North et al., 1968)	k = −8→9
T_min = 0.957, T_max = 0.979	l = −23→26
8410 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ²(F_o²) + (0.0375P)²] where P = (F_o² + 2F_c²)/3
3090 reflections	(Δ/σ)_max = 0.002
201 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₇H₁₆N₃O₃⁺·C₃H₄NO₃⁻	V = 1338.6 (4) Å³
M_r = 292.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.355 (2) Å	µ = 0.12 mm⁻¹
b = 6.996 (1) Å	T = 120 K
c = 20.606 (4) Å	0.30 × 0.24 × 0.20 mm
β = 96.99 (3)°

Data collection top

Nonius KappaCCD diffractometer	3090 independent reflections
Absorption correction: multi-scan (North et al., 1968)	1887 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.979	R_int = 0.049
8410 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	Δρ_max = 0.20 e Å⁻³
3090 reflections	Δρ_min = −0.25 e Å⁻³
201 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
O1	−0.84446 (13)	−0.16641 (17)	0.98706 (6)	0.0158 (3)
O2	−0.60613 (13)	−0.22237 (19)	1.00166 (6)	0.0180 (3)
O3	−0.84727 (14)	−0.3817 (2)	0.80265 (6)	0.0181 (3)
H3O	−0.939 (2)	−0.373 (3)	0.7840 (10)	0.027*
O4	0.55821 (13)	0.0801 (2)	0.88257 (6)	0.0193 (3)
H4O	0.583 (2)	0.126 (3)	0.9258 (10)	0.029*
O5	0.12037 (13)	0.11505 (19)	0.75400 (6)	0.0179 (3)
O6	−0.27505 (15)	−0.2615 (2)	1.00518 (6)	0.0211 (3)
H6O	−0.369 (2)	−0.261 (3)	0.9960 (9)	0.032*
N1	−0.85445 (16)	−0.3060 (2)	0.86557 (7)	0.0146 (4)
N2	0.41206 (16)	0.1204 (2)	0.87427 (7)	0.0153 (4)
N3	0.13295 (17)	0.1750 (2)	0.86292 (8)	0.0139 (4)
H3N	0.189 (2)	0.184 (3)	0.8990 (9)	0.021*
N4	−0.10824 (17)	−0.0767 (2)	0.90998 (7)	0.0121 (4)
H4N	−0.008 (2)	−0.108 (3)	0.9240 (9)	0.018*
H5N	−0.139 (2)	−0.009 (3)	0.9426 (9)	0.018*
C1	−0.7283 (2)	−0.2267 (3)	0.96857 (9)	0.0139 (4)
C2	−0.73259 (19)	−0.3166 (3)	0.90150 (9)	0.0125 (4)
C3	−0.59762 (19)	−0.4002 (3)	0.88233 (9)	0.0162 (4)
H3A	−0.6191	−0.4704	0.8423	0.024*
H3C	−0.5558	−0.4846	0.9162	0.024*
H3B	−0.5309	−0.2995	0.8762	0.024*
C4	0.4116 (2)	−0.0067 (3)	0.76127 (9)	0.0203 (5)
H4A	0.5142	−0.0162	0.7719	0.030*
H4B	0.3899	0.0728	0.7234	0.030*
H4C	0.3720	−0.1319	0.7523	0.030*
C5	0.3476 (2)	0.0790 (3)	0.81755 (9)	0.0124 (4)
C6	0.1903 (2)	0.1255 (3)	0.80944 (9)	0.0142 (4)
C7	−0.01883 (19)	0.2223 (3)	0.86077 (9)	0.0160 (4)
H7A	−0.0450	0.3120	0.8254	0.019*
H7B	−0.0345	0.2847	0.9013	0.019*
C8	−0.1158 (2)	0.0483 (3)	0.85087 (9)	0.0143 (4)
H8A	−0.2145	0.0903	0.8394	0.017*
H8B	−0.0887	−0.0260	0.8145	0.017*
C9	−0.19929 (19)	−0.2503 (3)	0.89620 (8)	0.0143 (4)
H9A	−0.1580	−0.3293	0.8646	0.017*
H9B	−0.2948	−0.2118	0.8770	0.017*
C10	−0.2118 (2)	−0.3664 (3)	0.95673 (9)	0.0171 (4)
H10A	−0.2698	−0.4789	0.9449	0.021*
H10B	−0.1167	−0.4091	0.9750	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0160 (7)	0.0177 (8)	0.0139 (7)	0.0013 (6)	0.0025 (5)	−0.0025 (6)
O2	0.0156 (8)	0.0239 (8)	0.0132 (7)	0.0003 (6)	−0.0028 (6)	−0.0031 (6)
O3	0.0161 (8)	0.0264 (8)	0.0114 (7)	0.0014 (7)	−0.0003 (6)	−0.0043 (6)
O4	0.0112 (7)	0.0286 (9)	0.0177 (8)	0.0035 (6)	−0.0002 (6)	−0.0047 (6)
O5	0.0154 (7)	0.0250 (8)	0.0127 (7)	0.0001 (6)	−0.0003 (6)	0.0020 (6)
O6	0.0173 (8)	0.0311 (9)	0.0157 (7)	−0.0033 (7)	0.0057 (6)	−0.0020 (6)
N1	0.0193 (9)	0.0160 (9)	0.0089 (8)	−0.0016 (7)	0.0030 (7)	−0.0017 (7)
N2	0.0095 (8)	0.0173 (9)	0.0193 (9)	0.0018 (7)	0.0022 (7)	0.0012 (7)
N3	0.0117 (9)	0.0180 (10)	0.0116 (9)	−0.0007 (7)	−0.0001 (6)	−0.0003 (7)
N4	0.0113 (9)	0.0159 (9)	0.0094 (8)	0.0011 (7)	0.0027 (7)	−0.0001 (7)
C1	0.0160 (11)	0.0116 (11)	0.0141 (10)	−0.0007 (8)	0.0017 (8)	0.0028 (8)
C2	0.0135 (10)	0.0101 (10)	0.0139 (10)	−0.0010 (8)	0.0022 (8)	0.0014 (8)
C3	0.0142 (10)	0.0197 (11)	0.0146 (10)	0.0003 (9)	0.0010 (8)	−0.0018 (9)
C4	0.0164 (11)	0.0276 (12)	0.0167 (11)	0.0011 (9)	0.0015 (9)	−0.0019 (9)
C5	0.0152 (10)	0.0096 (10)	0.0126 (10)	−0.0005 (8)	0.0024 (8)	0.0009 (8)
C6	0.0191 (11)	0.0097 (10)	0.0138 (10)	−0.0026 (8)	0.0023 (9)	0.0030 (8)
C7	0.0151 (11)	0.0161 (11)	0.0175 (11)	0.0009 (9)	0.0042 (8)	0.0016 (8)
C8	0.0123 (10)	0.0192 (12)	0.0115 (10)	0.0014 (9)	0.0017 (8)	0.0015 (8)
C9	0.0131 (10)	0.0150 (11)	0.0150 (10)	−0.0019 (8)	0.0022 (8)	−0.0019 (8)
C10	0.0174 (11)	0.0174 (11)	0.0172 (10)	0.0015 (9)	0.0047 (8)	0.0023 (9)

Geometric parameters (Å, º) top

O1—C1	1.266 (2)	C2—C3	1.488 (2)
O2—C1	1.258 (2)	C3—H3A	0.9600
O3—N1	1.4095 (18)	C3—H3C	0.9600
O3—H3O	0.90 (2)	C3—H3B	0.9600
O4—N2	1.3861 (19)	C4—C5	1.494 (2)
O4—H4O	0.95 (2)	C4—H4A	0.9600
O5—C6	1.248 (2)	C4—H4B	0.9600
O6—C10	1.424 (2)	C4—H4C	0.9600
O6—H6O	0.87 (2)	C5—C6	1.497 (2)
N1—C2	1.284 (2)	C7—C8	1.518 (2)
N2—C5	1.281 (2)	C7—H7A	0.9700
N3—C6	1.329 (2)	C7—H7B	0.9700
N3—C7	1.453 (2)	C8—H8A	0.9700
N3—H3N	0.86 (2)	C8—H8B	0.9700
N4—C9	1.491 (2)	C9—C10	1.505 (2)
N4—C8	1.494 (2)	C9—H9A	0.9700
N4—H4N	0.970 (19)	C9—H9B	0.9700
N4—H5N	0.895 (18)	C10—H10A	0.9700
C1—C2	1.515 (2)	C10—H10B	0.9700

N1—O3—H3O	102.4 (12)	H4B—C4—H4C	109.5
N2—O4—H4O	99.8 (12)	N2—C5—C4	127.62 (17)
C10—O6—H6O	110.1 (13)	N2—C5—C6	113.55 (15)
C2—N1—O3	111.74 (14)	C4—C5—C6	118.83 (16)
C5—N2—O4	114.45 (14)	O5—C6—N3	123.72 (18)
C6—N3—C7	121.71 (16)	O5—C6—C5	119.22 (16)
C6—N3—H3N	118.4 (13)	N3—C6—C5	117.05 (16)
C7—N3—H3N	119.8 (13)	N3—C7—C8	112.78 (15)
C9—N4—C8	110.61 (14)	N3—C7—H7A	109.0
C9—N4—H4N	112.3 (11)	C8—C7—H7A	109.0
C8—N4—H4N	108.9 (11)	N3—C7—H7B	109.0
C9—N4—H5N	110.3 (12)	C8—C7—H7B	109.0
C8—N4—H5N	108.5 (12)	H7A—C7—H7B	107.8
H4N—N4—H5N	106.1 (16)	N4—C8—C7	113.05 (15)
O2—C1—O1	125.82 (17)	N4—C8—H8A	109.0
O2—C1—C2	115.20 (16)	C7—C8—H8A	109.0
O1—C1—C2	118.98 (17)	N4—C8—H8B	109.0
N1—C2—C3	126.33 (17)	C7—C8—H8B	109.0
N1—C2—C1	115.17 (16)	H8A—C8—H8B	107.8
C3—C2—C1	118.46 (16)	N4—C9—C10	112.47 (15)
C2—C3—H3A	109.5	N4—C9—H9A	109.1
C2—C3—H3C	109.5	C10—C9—H9A	109.1
H3A—C3—H3C	109.5	N4—C9—H9B	109.1
C2—C3—H3B	109.5	C10—C9—H9B	109.1
H3A—C3—H3B	109.5	H9A—C9—H9B	107.8
H3C—C3—H3B	109.5	O6—C10—C9	112.58 (15)
C5—C4—H4A	109.5	O6—C10—H10A	109.1
C5—C4—H4B	109.5	C9—C10—H10A	109.1
H4A—C4—H4B	109.5	O6—C10—H10B	109.1
C5—C4—H4C	109.5	C9—C10—H10B	109.1
H4A—C4—H4C	109.5	H10A—C10—H10B	107.8

O3—N1—C2—C3	−1.2 (3)	N2—C5—C6—O5	170.68 (17)
O3—N1—C2—C1	176.22 (14)	C4—C5—C6—O5	−9.1 (3)
O2—C1—C2—N1	−174.16 (17)	N2—C5—C6—N3	−9.8 (2)
O1—C1—C2—N1	7.0 (2)	C4—C5—C6—N3	170.42 (17)
O2—C1—C2—C3	3.4 (2)	C6—N3—C7—C8	73.0 (2)
O1—C1—C2—C3	−175.41 (17)	C9—N4—C8—C7	−176.88 (15)
O4—N2—C5—C4	0.4 (3)	N3—C7—C8—N4	72.22 (18)
O4—N2—C5—C6	−179.41 (14)	C8—N4—C9—C10	−171.87 (14)
C7—N3—C6—O5	−0.2 (3)	N4—C9—C10—O6	60.2 (2)
C7—N3—C6—C5	−179.75 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O5ⁱ	0.90 (2)	1.78 (2)	2.677 (2)	173 (2)
O4—H4O···O2ⁱⁱ	0.95 (2)	1.63 (2)	2.5733 (18)	172.3 (19)
O6—H6O···O2	0.87 (2)	2.25 (2)	3.101 (2)	163.4 (18)
N3—H3N···O6ⁱⁱ	0.86 (2)	2.11 (2)	2.940 (2)	162.6 (18)
N4—H4N···O1ⁱⁱⁱ	0.970 (19)	1.93 (2)	2.838 (2)	155.1 (15)
N4—H5N···O1^iv	0.895 (18)	1.921 (19)	2.796 (2)	165.1 (17)

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

Experimental details

Crystal data
Chemical formula	C₇H₁₆N₃O₃⁺·C₃H₄NO₃⁻
M_r	292.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	9.355 (2), 6.996 (1), 20.606 (4)
β (°)	96.99 (3)
V (Å³)	1338.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.30 × 0.24 × 0.20

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (North et al., 1968)
T_min, T_max	0.957, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	8410, 3090, 1887
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.088, 0.92
No. of reflections	3090
No. of parameters	201
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.25

Computer programs: COLLECT (Bruker, 2004), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O5ⁱ	0.90 (2)	1.78 (2)	2.677 (2)	173 (2)
O4—H4O···O2ⁱⁱ	0.95 (2)	1.63 (2)	2.5733 (18)	172.3 (19)
O6—H6O···O2	0.87 (2)	2.25 (2)	3.101 (2)	163.4 (18)
N3—H3N···O6ⁱⁱ	0.86 (2)	2.11 (2)	2.940 (2)	162.6 (18)
N4—H4N···O1ⁱⁱⁱ	0.970 (19)	1.93 (2)	2.838 (2)	155.1 (15)
N4—H5N···O1^iv	0.895 (18)	1.921 (19)	2.796 (2)	165.1 (17)

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

Acknowledgements

The authors thank the Ministry of Education and Science of Ukraine for financial support (grant No. F28/241–2009).

References

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Volume 65| Part 9| September 2009| Pages o2077-o2078

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

N-(2-Hy­droxy­ethyl)-2-[2-(hy­droxy­imino)propanamido]ethanaminium 2-(hy­droxy­imino)propanoate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-(2-Hydroxyethyl)-2-[2-(hydroxyimino)propanamido]ethanaminium 2-(hydroxyimino)propanoate