N-(2-Hydroxy-ethyl)-2-[2-(hydroxy-imino)propanamido]ethanaminium 2-(hydroxy-imino)propanoate.

The cation of the title salt, C(7)H(16)N(3)O(3) (+)·C(3)H(4)NO(3) (-), 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 = 292.30

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.088

S = 0.92

3090 reflections

201 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

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.

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

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

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

C7H16N3O3+·C3H4NO3−	F(000) = 624
Mr = 292.30	Dx = 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

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

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(Fo2) + (0.0375P)2] where P = (Fo2 + 2Fc2)/3
3090 reflections	(Δ/σ)max = 0.002
201 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.25 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
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*

	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)

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)

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···O1iv	0.895 (18)	1.921 (19)	2.796 (2)	165.1 (17)

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⋯O1iv	0.895 (18)	1.921 (19)	2.796 (2)	165.1 (17)

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