2-[(2-Hy-droxy-eth-yl)aza-nium-yl]ethanaminium oxalate monohydrate.

In the title hydrated mol-ecular salt, C(4)H(14)N(2)O(2+)·C(2)O(4) (2-)·H(2)O, the oxalate dianion is almost planar (r.m.s. deviation = 0.020 Å). In the crystal, the components are linked by N-H⋯O(water), N-H⋯O(oxalate) O-H(ammonium)⋯O(oxalate), O-H(water)⋯O(oxalate) and O-H(water)⋯O(ammonium) hydrogen bonds, thereby forming a complex three-dimensional packing motif.

Related literature

For related structures, see: Sakai et al. (2003 ▶); Kolitsch (2004 ▶); Cotton et al. (1996 ▶); Barnes (2003 ▶).

Experimental

Crystal data

C4H14N2O2+·C2O4 2−·H2O

M = 212.21

Monoclinic,

a = 5.7311 (11) Å

b = 13.136 (3) Å

c = 6.7373 (13) Å

β = 102.52 (3)°

V = 495.16 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.3 × 0.3 × 0.2 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.489, T max = 1.000

5068 measured reflections

2261 independent reflections

1853 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.086

S = 0.97

2261 reflections

135 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 datablock(s) I, global. DOI: 10.1107/S1600536811056157/hb6584sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811056157/hb6584Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811056157/hb6584Isup3.cml

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

C4H14N2O2+·C2O42−·H2O	F(000) = 228
Mr = 212.21	Dx = 1.423 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3450 reflections
a = 5.7311 (11) Å	θ = 6.2–55.3°
b = 13.136 (3) Å	µ = 0.13 mm−1
c = 6.7373 (13) Å	T = 293 K
β = 102.52 (3)°	Block, colorless
V = 495.16 (17) Å3	0.3 × 0.3 × 0.2 mm
Z = 2

Rigaku Mercury CCD diffractometer	2261 independent reflections
Radiation source: fine-focus sealed tube	1853 reflections with I > 2σ(I)
graphite	Rint = 0.046
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −7→7
Tmin = 0.489, Tmax = 1.000	k = −16→16
5068 measured reflections	l = −8→8

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.0314P)2] where P = (Fo2 + 2Fc2)/3
2261 reflections	(Δ/σ)max < 0.001
135 parameters	Δρmax = 0.22 e Å−3
3 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
C1	1.1138 (4)	0.63105 (16)	0.1821 (3)	0.0342 (5)
H1D	1.1520	0.5976	0.0648	0.041*
H1E	1.0764	0.7017	0.1467	0.041*
C2	0.9023 (4)	0.58091 (12)	0.2350 (3)	0.0290 (4)
H2B	0.8808	0.6071	0.3644	0.035*
H2C	0.7607	0.5980	0.1328	0.035*
C3	0.6935 (4)	0.41905 (13)	0.2318 (3)	0.0256 (4)
H3A	0.5915	0.4347	0.1007	0.031*
H3B	0.6171	0.4452	0.3365	0.031*
C4	0.7217 (4)	0.30554 (15)	0.2545 (3)	0.0284 (5)
H4A	0.8062	0.2791	0.1555	0.034*
H4B	0.8127	0.2888	0.3895	0.034*
C5	0.2891 (3)	0.33640 (13)	0.6829 (2)	0.0213 (4)
C6	0.1213 (3)	0.39951 (13)	0.7871 (3)	0.0234 (4)
H1W	0.472 (5)	0.541 (3)	0.636 (3)	0.117 (14)*
H2W	0.702 (3)	0.522 (2)	0.723 (3)	0.057 (9)*
N1	0.4808 (3)	0.26039 (11)	0.2219 (2)	0.0244 (4)
H1A	0.4931	0.1931	0.2351	0.037*
H1B	0.3992	0.2758	0.0975	0.037*
H1F	0.4048	0.2851	0.3134	0.037*
N2	0.9269 (3)	0.46896 (11)	0.2484 (2)	0.0210 (3)
H2A	0.9948	0.4465	0.1480	0.025*
H2D	1.0235	0.4521	0.3678	0.025*
O1	1.3118 (3)	0.62633 (11)	0.3457 (2)	0.0453 (4)
H1C	1.4124	0.6679	0.3285	0.068*
O2	0.2737 (3)	0.35255 (12)	0.49926 (18)	0.0391 (4)
O3	0.4216 (3)	0.27372 (10)	0.78762 (18)	0.0320 (3)
O4	0.1307 (3)	0.38042 (10)	0.96855 (18)	0.0333 (3)
O5	−0.0084 (3)	0.46250 (12)	0.6815 (2)	0.0429 (4)
O1W	0.5752 (3)	0.54801 (12)	0.7448 (2)	0.0425 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0382 (13)	0.0278 (9)	0.0369 (10)	−0.0049 (9)	0.0084 (9)	0.0046 (8)
C2	0.0263 (11)	0.0223 (9)	0.0374 (10)	0.0008 (8)	0.0044 (8)	0.0020 (8)
C3	0.0216 (11)	0.0251 (9)	0.0314 (10)	−0.0002 (8)	0.0081 (8)	−0.0009 (7)
C4	0.0241 (11)	0.0250 (9)	0.0375 (11)	0.0007 (9)	0.0102 (9)	−0.0023 (8)
C5	0.0188 (10)	0.0222 (8)	0.0227 (8)	−0.0017 (7)	0.0045 (7)	0.0004 (7)
C6	0.0231 (11)	0.0248 (9)	0.0220 (8)	−0.0004 (8)	0.0039 (8)	−0.0028 (7)
N1	0.0279 (10)	0.0218 (7)	0.0242 (7)	−0.0011 (7)	0.0071 (7)	0.0015 (6)
N2	0.0213 (9)	0.0226 (7)	0.0192 (7)	0.0018 (7)	0.0047 (6)	0.0004 (6)
O1	0.0344 (9)	0.0474 (9)	0.0505 (9)	−0.0138 (8)	0.0015 (7)	0.0129 (7)
O2	0.0393 (10)	0.0576 (10)	0.0234 (7)	0.0198 (8)	0.0138 (6)	0.0067 (6)
O3	0.0358 (9)	0.0320 (7)	0.0290 (7)	0.0148 (7)	0.0086 (6)	0.0043 (5)
O4	0.0371 (9)	0.0424 (8)	0.0234 (6)	0.0127 (7)	0.0128 (6)	0.0031 (6)
O5	0.0495 (11)	0.0490 (8)	0.0305 (7)	0.0281 (8)	0.0091 (7)	0.0080 (7)
O1W	0.0448 (11)	0.0345 (8)	0.0478 (10)	0.0076 (8)	0.0091 (8)	−0.0079 (7)

C1—O1	1.402 (2)	C5—O3	1.233 (2)
C1—C2	1.489 (3)	C5—O2	1.239 (2)
C1—H1D	0.9700	C5—C6	1.548 (3)
C1—H1E	0.9700	C6—O5	1.230 (2)
C2—N2	1.478 (2)	C6—O4	1.238 (2)
C2—H2B	0.9700	N1—H1A	0.8900
C2—H2C	0.9700	N1—H1B	0.8900
C3—N2	1.472 (2)	N1—H1F	0.8900
C3—C4	1.504 (3)	N2—H2A	0.9000
C3—H3A	0.9700	N2—H2D	0.9000
C3—H3B	0.9700	O1—H1C	0.8200
C4—N1	1.475 (3)	O1W—H1W	0.838 (10)
C4—H4A	0.9700	O1W—H2W	0.841 (10)
C4—H4B	0.9700
O1—C1—C2	110.75 (16)	C3—C4—H4B	110.1
O1—C1—H1D	109.5	H4A—C4—H4B	108.4
C2—C1—H1D	109.5	O3—C5—O2	125.95 (17)
O1—C1—H1E	109.5	O3—C5—C6	117.66 (14)
C2—C1—H1E	109.5	O2—C5—C6	116.37 (15)
H1D—C1—H1E	108.1	O5—C6—O4	126.77 (19)
N2—C2—C1	112.53 (17)	O5—C6—C5	117.06 (15)
N2—C2—H2B	109.1	O4—C6—C5	116.18 (14)
C1—C2—H2B	109.1	C4—N1—H1A	109.5
N2—C2—H2C	109.1	C4—N1—H1B	109.5
C1—C2—H2C	109.1	H1A—N1—H1B	109.5
H2B—C2—H2C	107.8	C4—N1—H1F	109.5
N2—C3—C4	110.98 (15)	H1A—N1—H1F	109.5
N2—C3—H3A	109.4	H1B—N1—H1F	109.5
C4—C3—H3A	109.4	C3—N2—C2	111.45 (14)
N2—C3—H3B	109.4	C3—N2—H2A	109.3
C4—C3—H3B	109.4	C2—N2—H2A	109.3
H3A—C3—H3B	108.0	C3—N2—H2D	109.3
N1—C4—C3	107.88 (16)	C2—N2—H2D	109.3
N1—C4—H4A	110.1	H2A—N2—H2D	108.0
C3—C4—H4A	110.1	C1—O1—H1C	109.5
N1—C4—H4B	110.1	H1W—O1W—H2W	106 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1Wi	0.89	1.96	2.823 (2)	164
N1—H1B···O3ii	0.89	2.12	2.8769 (19)	143
N1—H1B···O4ii	0.89	2.11	2.818 (2)	136
N1—H1F···O2	0.89	1.82	2.707 (2)	172
N2—H2A···O4iii	0.90	1.80	2.688 (2)	170
N2—H2D···O5iv	0.90	2.16	2.862 (2)	134
N2—H2D···O2iv	0.90	2.00	2.773 (2)	143
O1—H1C···O3v	0.82	1.94	2.736 (2)	163
O1W—H2W···O5iv	0.84 (1)	1.91 (1)	2.753 (2)	178 (2)
O1W—H1W···O1vi	0.84 (1)	2.27 (3)	2.968 (2)	141 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1Wi	0.89	1.96	2.823 (2)	164
N1—H1B⋯O3ii	0.89	2.12	2.8769 (19)	143
N1—H1B⋯O4ii	0.89	2.11	2.818 (2)	136
N1—H1F⋯O2	0.89	1.82	2.707 (2)	172
N2—H2A⋯O4iii	0.90	1.80	2.688 (2)	170
N2—H2D⋯O5iv	0.90	2.16	2.862 (2)	134
N2—H2D⋯O2iv	0.90	2.00	2.773 (2)	143
O1—H1C⋯O3v	0.82	1.94	2.736 (2)	163
O1W—H2W⋯O5iv	0.84 (1)	1.91 (1)	2.753 (2)	178 (2)
O1W—H1W⋯O1vi	0.84 (1)	2.27 (3)	2.968 (2)	141 (4)

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