N,N′-Bis(2-hydroxy­ethyl)-N,N′-[ethyl­ene­dioxy­bis(o-phenyl­enemethyl­ene)]­diammonium fumarate tetra­hydrate

Bai, H.-Y.; Liu, H.-Y.; Ma, J.-F.

doi:10.1107/S1600536808033746

organic compounds

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Volume 64| Part 11| November 2008| Page o2162

doi:10.1107/S1600536808033746

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N,N′-Bis(2-hydroxyethyl)-N,N′-[ethylenedioxybis(o-phenylenemethylene)]diammonium fumarate tetrahydrate

Hong-Ye Bai,^a Hai-Yan Liu ^a and Jian-Fang Ma ^a ^*

^aDepartment of Chemistry, Northeast Normal University, Changchun 130024, People's Republic of China
^*Correspondence e-mail: majf247nenu@yahoo.com.cn

(Received 17 September 2008; accepted 16 October 2008; online 22 October 2008)

The reaction of 1,2-bis{2-[(2-hydroxyethyl)aminomethyl]phenoxy}ethane and fumaric acid in a mixed solution in ethanol–water (1:1 v/v) yields the title compound, C₂₀H₃₀N₂O₄²⁺·C₄H₂O₄²⁻·4H₂O. In the crystal structure, the anions, cations and water molecules are connected via O—H⋯O and N—H⋯O hydrogen bonds into a three-dimensional network. The fumarate anion and the N,N′-bis(2-hydroxyethyl)-N,N′-[ethylenedioxybis(o-phenylenemethylene)]diammonium cation are located on centers of inversion, whereas the two crystallographically independent water molecules occupy general positions.

Related literature

For a related structure, see: Wang & Wei (2005 ). For background to the synthesis, see: Armstrong & Lindoy (1975 ).

Experimental

Crystal data

C₂₀H₃₀N₂O₄²⁺·C₄H₂O₄²⁻·4H₂O
M_r = 548.58
Triclinic, $[P \overline 1]$
a = 7.585 (7) Å
b = 8.623 (6) Å
c = 11.515 (7) Å
α = 104.64 (2)°
β = 96.77 (3)°
γ = 104.29 (3)°
V = 693.0 (9) Å³
Z = 1
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 (2) K
0.41 × 0.34 × 0.28 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.952, T_max = 0.983
6826 measured reflections
3128 independent reflections
2394 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.128
S = 1.11
3128 reflections
193 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1C⋯O2W	0.85 (3)	1.97 (3)	2.792 (3)	164 (3)
O2W—H2C⋯O2	0.85 (3)	1.97 (3)	2.828 (3)	176 (3)
N5—H5B⋯O2	0.950 (19)	1.811 (19)	2.749 (2)	168.6 (16)
O1W—H1D⋯O3ⁱ	0.91 (3)	1.96 (3)	2.830 (3)	159 (3)
O2W—H2D⋯O4ⁱⁱ	0.86 (3)	2.01 (3)	2.867 (3)	175 (3)
N5—H5A⋯O1Wⁱⁱⁱ	0.900 (19)	2.125 (19)	2.925 (3)	147.6 (15)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x-1, y-1, z; (iii) x+1, y, z.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; 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/S1600536808033746/nc2116sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033746/nc2116Isup2.hkl

checkCIF report

Comment top

Currently, many groups are investigating crystal structures of cocrystals containing organic acids and organic bases, which are based on hydrogen bonding (Wang & Wei, 2005). In this context, the crystal structure of the title compound is presented.

The crystal structure consists of one N,N'-bis(2-hydroxyethyl)-N,N'-[ethylenedioxybis(o-phenylenemethylene)]diammonium cation and one fumarate anion located on centers of inversion and two crystallographically independent water molecules that occupy general positions (Fig. 1). In the crystal structure, different O—H···O and N—H···O hydrogen bonds link the components of the title compound into a three-dimensional network (Table 1 and Fig. 2).

Related literature top

For a related structure, see: Wang & Wei (2005). For background to the synthesis, see: Armstrong & Lindoy (1975). [Please check added text]

Experimental top

All chemicals were obtained from commercial sources and used without further purification except for L (L is 1,2-bis{2-[(2-hydroxyethyl)aminomethyl]phenoxy}ethane). 1,4-bis(2-formylphenyl)-1,4-dioxabutuane, which was prepared according to the literature (Armstrong & Lindoy, 1975). 2-aminoethanol (1.22 g, 2.0 mol) in 50 ml of methanol were added slowly to a stirred boiling solution of 1,4-bis(2'-formylphenyl)-1,4-dioxabutuane (2.70 g, 1 mol) in 100 ml of methanol. The mixed solution was refluxed for 1 h, filtered off and cooled to room temperature. 1.52 g NaBH₄ were added slowly to the filtrate and stirred for a further 2 h. The solvent was evaporated and 100 ml water of were added. After extraction with chloroform the solvent was evaporated, which led to a white solid of L. Crystals of the title compound were obtained by dissolving L (0.180 g, 1 mmol) and fumaric acid (0.116 g, 1 mmol) in a mixture of ethanol and water (1:1), followed by slow evaporation of the solvents.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); 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. Crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 30% probability level (for the H atoms spheres of arbitrary size are used). Symmetry codes: (i) -x + 2, -y + 1, -z + 1; (ii) -x + 1, -y, -z + 2.
	Fig. 2. Crystal structure of the title compound with hydrogen bonding indicated by dashed lines. For clarity, H atoms not involved in hydrogen bonding are omitted.

N,N'-Bis(2-hydroxyethyl)-N,N'-[ethylenedioxybis(o-phenylenemethylene)]diammonium fumarate tetrahydrate top

Crystal data top

C₂₀H₃₀N₂O₄²⁺·C₄H₂O₄²⁻·4H₂O	Z = 1
M_r = 548.58	F(000) = 294
Triclinic, P1	D_x = 1.315 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 7.585 (7) Å	Cell parameters from 3128 reflections
b = 8.623 (6) Å	θ = 3.1–27.4°
c = 11.515 (7) Å	µ = 0.11 mm⁻¹
α = 104.64 (2)°	T = 293 K
β = 96.77 (3)°	Block, colourless
γ = 104.29 (3)°	0.41 × 0.34 × 0.28 mm
V = 693.0 (9) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	3128 independent reflections
Radiation source: fine-focus sealed tube	2394 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.4°, θ_min = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→10
T_min = 0.952, T_max = 0.983	l = −14→14
6826 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0619P)² + 0.1182P] where P = (F_o² + 2F_c²)/3
3128 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₀H₃₀N₂O₄²⁺·C₄H₂O₄²⁻·4H₂O	γ = 104.29 (3)°
M_r = 548.58	V = 693.0 (9) Å³
Triclinic, P1	Z = 1
a = 7.585 (7) Å	Mo Kα radiation
b = 8.623 (6) Å	µ = 0.11 mm⁻¹
c = 11.515 (7) Å	T = 293 K
α = 104.64 (2)°	0.41 × 0.34 × 0.28 mm
β = 96.77 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3128 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2394 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.983	R_int = 0.018
6826 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.68 e Å⁻³
3128 reflections	Δρ_min = −0.20 e Å⁻³
193 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
C1	0.4884 (2)	0.33265 (18)	0.58122 (12)	0.0353 (3)
C2	0.3124 (2)	0.2213 (2)	0.54836 (15)	0.0470 (4)
H2	0.2257	0.2368	0.5977	0.056*
C3	0.2632 (3)	0.0871 (2)	0.44313 (17)	0.0582 (5)
H3	0.1438	0.0140	0.4212	0.070*
C4	0.3923 (3)	0.0628 (2)	0.37144 (15)	0.0576 (5)
H4	0.3599	−0.0284	0.3015	0.069*
C5	0.5695 (3)	0.1718 (2)	0.40173 (14)	0.0507 (4)
H5	0.6560	0.1539	0.3528	0.061*
C6	0.6173 (2)	0.3083 (2)	0.50592 (12)	0.0388 (3)
C7	0.5438 (2)	0.48184 (19)	0.69256 (13)	0.0381 (3)
H7A	0.5907	0.5822	0.6688	0.046*
H7B	0.4355	0.4914	0.7277	0.046*
C8	0.7528 (2)	0.61530 (18)	0.90008 (13)	0.0406 (3)
H8A	0.8408	0.5931	0.9574	0.049*
H8B	0.6472	0.6266	0.9380	0.049*
C9	0.8425 (2)	0.77871 (19)	0.87634 (15)	0.0471 (4)
H9A	0.7507	0.8081	0.8269	0.056*
H9B	0.8863	0.8665	0.9536	0.056*
C10	0.9210 (2)	0.4234 (2)	0.46928 (15)	0.0532 (4)
H10A	0.8711	0.4244	0.3880	0.064*
H10B	0.9610	0.3235	0.4623	0.064*
C11	0.6218 (2)	0.21555 (18)	0.97927 (15)	0.0403 (3)
C12	0.5574 (2)	0.07174 (19)	1.03092 (14)	0.0431 (4)
H12	0.6033	0.0873	1.1129	0.052*
O1	0.78557 (15)	0.42777 (16)	0.54483 (10)	0.0503 (3)
O2	0.52895 (15)	0.21994 (13)	0.88286 (10)	0.0485 (3)
O3	0.76640 (19)	0.32235 (16)	1.03867 (13)	0.0684 (4)
O1W	0.0354 (2)	0.3790 (2)	0.77573 (13)	0.0646 (4)
H1C	0.050 (4)	0.289 (4)	0.787 (2)	0.097*
H1D	0.122 (4)	0.462 (4)	0.836 (3)	0.097*
O2W	0.1427 (2)	0.09631 (18)	0.79075 (15)	0.0672 (4)
H2C	0.260 (5)	0.129 (4)	0.818 (3)	0.101*
H2D	0.101 (4)	−0.004 (4)	0.795 (3)	0.101*
O4	0.99312 (17)	0.76942 (15)	0.81566 (12)	0.0521 (3)
H4A	1.073 (3)	0.739 (3)	0.860 (2)	0.078*
N5	0.68936 (17)	0.46959 (14)	0.78706 (10)	0.0310 (3)
H5A	0.792 (3)	0.458 (2)	0.7581 (16)	0.046*
H5B	0.638 (2)	0.374 (2)	0.8117 (15)	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0385 (8)	0.0408 (8)	0.0311 (6)	0.0160 (6)	0.0048 (5)	0.0145 (6)
C2	0.0411 (9)	0.0564 (10)	0.0431 (8)	0.0116 (7)	0.0047 (7)	0.0178 (7)
C3	0.0580 (11)	0.0534 (10)	0.0505 (10)	0.0022 (9)	−0.0066 (8)	0.0145 (8)
C4	0.0831 (14)	0.0453 (9)	0.0381 (8)	0.0208 (9)	−0.0048 (8)	0.0062 (7)
C5	0.0675 (12)	0.0614 (10)	0.0326 (7)	0.0346 (9)	0.0104 (7)	0.0139 (7)
C6	0.0426 (8)	0.0501 (9)	0.0309 (7)	0.0206 (7)	0.0070 (6)	0.0172 (6)
C7	0.0407 (8)	0.0432 (8)	0.0363 (7)	0.0194 (6)	0.0082 (6)	0.0142 (6)
C8	0.0494 (9)	0.0363 (8)	0.0324 (7)	0.0077 (7)	0.0096 (6)	0.0077 (6)
C9	0.0546 (10)	0.0323 (8)	0.0485 (8)	0.0073 (7)	0.0042 (7)	0.0095 (7)
C10	0.0455 (9)	0.0832 (13)	0.0438 (9)	0.0271 (9)	0.0210 (7)	0.0269 (9)
C11	0.0413 (8)	0.0330 (7)	0.0523 (9)	0.0105 (6)	0.0112 (7)	0.0213 (7)
C12	0.0460 (9)	0.0398 (8)	0.0414 (8)	0.0063 (6)	0.0036 (6)	0.0166 (6)
O1	0.0404 (6)	0.0728 (8)	0.0381 (6)	0.0139 (6)	0.0152 (5)	0.0156 (5)
O2	0.0438 (6)	0.0429 (6)	0.0542 (7)	−0.0019 (5)	0.0034 (5)	0.0230 (5)
O3	0.0600 (8)	0.0487 (7)	0.0848 (10)	−0.0074 (6)	−0.0187 (7)	0.0361 (7)
O1W	0.0677 (9)	0.0684 (9)	0.0612 (8)	0.0352 (8)	0.0032 (6)	0.0141 (7)
O2W	0.0480 (8)	0.0537 (8)	0.1011 (11)	0.0065 (6)	−0.0001 (7)	0.0393 (8)
O4	0.0433 (7)	0.0515 (7)	0.0639 (7)	0.0049 (5)	0.0056 (5)	0.0319 (6)
N5	0.0327 (6)	0.0306 (6)	0.0313 (6)	0.0079 (5)	0.0087 (5)	0.0122 (5)

Geometric parameters (Å, º) top

C1—C2	1.383 (2)	C9—O4	1.416 (2)
C1—C6	1.400 (2)	C9—H9A	0.9700
C1—C7	1.499 (2)	C9—H9B	0.9700
C2—C3	1.385 (3)	C10—O1	1.424 (2)
C2—H2	0.9300	C10—C10ⁱ	1.492 (4)
C3—C4	1.374 (3)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
C4—C5	1.383 (3)	C11—O3	1.235 (2)
C4—H4	0.9300	C11—O2	1.257 (2)
C5—C6	1.389 (2)	C11—C12	1.508 (2)
C5—H5	0.9300	C12—C12ⁱⁱ	1.293 (3)
C6—O1	1.369 (2)	C12—H12	0.9300
C7—N5	1.499 (2)	O1W—H1C	0.85 (3)
C7—H7A	0.9700	O1W—H1D	0.91 (3)
C7—H7B	0.9700	O2W—H2C	0.85 (3)
C8—N5	1.494 (2)	O2W—H2D	0.86 (3)
C8—C9	1.513 (2)	O4—H4A	0.88 (3)
C8—H8A	0.9700	N5—H5A	0.900 (19)
C8—H8B	0.9700	N5—H5B	0.950 (19)

C2—C1—C6	118.93 (15)	H8A—C8—H8B	107.7
C2—C1—C7	122.15 (14)	O4—C9—C8	112.16 (13)
C6—C1—C7	118.89 (14)	O4—C9—H9A	109.2
C1—C2—C3	120.98 (17)	C8—C9—H9A	109.2
C1—C2—H2	119.5	O4—C9—H9B	109.2
C3—C2—H2	119.5	C8—C9—H9B	109.2
C4—C3—C2	119.45 (18)	H9A—C9—H9B	107.9
C4—C3—H3	120.3	O1—C10—C10ⁱ	105.74 (17)
C2—C3—H3	120.3	O1—C10—H10A	110.6
C3—C4—C5	121.00 (17)	C10ⁱ—C10—H10A	110.6
C3—C4—H4	119.5	O1—C10—H10B	110.6
C5—C4—H4	119.5	C10ⁱ—C10—H10B	110.6
C4—C5—C6	119.42 (17)	H10A—C10—H10B	108.7
C4—C5—H5	120.3	O3—C11—O2	125.21 (14)
C6—C5—H5	120.3	O3—C11—C12	114.98 (14)
O1—C6—C5	125.51 (15)	O2—C11—C12	119.81 (14)
O1—C6—C1	114.30 (14)	C12ⁱⁱ—C12—C11	124.47 (19)
C5—C6—C1	120.19 (16)	C12ⁱⁱ—C12—H12	117.8
N5—C7—C1	112.04 (12)	C11—C12—H12	117.8
N5—C7—H7A	109.2	C6—O1—C10	118.86 (13)
C1—C7—H7A	109.2	H1C—O1W—H1D	104 (2)
N5—C7—H7B	109.2	H2C—O2W—H2D	108 (3)
C1—C7—H7B	109.2	C9—O4—H4A	108.2 (15)
H7A—C7—H7B	107.9	C8—N5—C7	114.91 (12)
N5—C8—C9	113.42 (13)	C8—N5—H5A	106.3 (11)
N5—C8—H8A	108.9	C7—N5—H5A	112.5 (11)
C9—C8—H8A	108.9	C8—N5—H5B	106.9 (10)
N5—C8—H8B	108.9	C7—N5—H5B	107.6 (10)
C9—C8—H8B	108.9	H5A—N5—H5B	108.3 (15)

C6—C1—C2—C3	0.3 (2)	C2—C1—C7—N5	114.29 (16)
C7—C1—C2—C3	178.16 (14)	C6—C1—C7—N5	−67.81 (17)
C1—C2—C3—C4	1.1 (3)	N5—C8—C9—O4	−55.82 (19)
C2—C3—C4—C5	−1.0 (3)	O3—C11—C12—C12ⁱⁱ	−160.5 (2)
C3—C4—C5—C6	−0.3 (3)	O2—C11—C12—C12ⁱⁱ	19.9 (3)
C4—C5—C6—O1	−178.31 (14)	C5—C6—O1—C10	5.5 (2)
C4—C5—C6—C1	1.6 (2)	C1—C6—O1—C10	−174.42 (13)
C2—C1—C6—O1	178.34 (12)	C10ⁱ—C10—O1—C6	174.87 (16)
C7—C1—C6—O1	0.37 (18)	C9—C8—N5—C7	−61.95 (18)
C2—C1—C6—C5	−1.6 (2)	C1—C7—N5—C8	179.32 (12)
C7—C1—C6—C5	−179.58 (13)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1C···O2W	0.85 (3)	1.97 (3)	2.792 (3)	164 (3)
O2W—H2C···O2	0.85 (3)	1.97 (3)	2.828 (3)	176 (3)
N5—H5B···O2	0.950 (19)	1.811 (19)	2.749 (2)	168.6 (16)
O1W—H1D···O3ⁱⁱⁱ	0.91 (3)	1.96 (3)	2.830 (3)	159 (3)
O2W—H2D···O4^iv	0.86 (3)	2.01 (3)	2.867 (3)	175 (3)
N5—H5A···O1W^v	0.900 (19)	2.125 (19)	2.925 (3)	147.6 (15)

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

Experimental details

Crystal data
Chemical formula	C₂₀H₃₀N₂O₄²⁺·C₄H₂O₄²⁻·4H₂O
M_r	548.58
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.585 (7), 8.623 (6), 11.515 (7)
α, β, γ (°)	104.64 (2), 96.77 (3), 104.29 (3)
V (Å³)	693.0 (9)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.41 × 0.34 × 0.28

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.952, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	6826, 3128, 2394
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.128, 1.11
No. of reflections	3128
No. of parameters	193
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.20

Computer programs: PROCESS-AUTO (Rigaku, 1998), 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
O1W—H1C···O2W	0.85 (3)	1.97 (3)	2.792 (3)	164 (3)
O2W—H2C···O2	0.85 (3)	1.97 (3)	2.828 (3)	176 (3)
N5—H5B···O2	0.950 (19)	1.811 (19)	2.749 (2)	168.6 (16)
O1W—H1D···O3ⁱ	0.91 (3)	1.96 (3)	2.830 (3)	159 (3)
O2W—H2D···O4ⁱⁱ	0.86 (3)	2.01 (3)	2.867 (3)	175 (3)
N5—H5A···O1Wⁱⁱⁱ	0.900 (19)	2.125 (19)	2.925 (3)	147.6 (15)

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

Acknowledgements

We thank the Program for New Century Excellent Talents in Chinese Universities (grant No. NCET-05-0320) and the Analysis and Testing Foundation of Northeast Normal University for support.

References

Armstrong, L. G. & Lindoy, L. F. (1975). Inorg. Chem. 14, 1322–1326. CrossRef CAS Web of Science Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Z.-L. & Wei, L.-H. (2005). Acta Cryst. E61, o3129–o3130. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 11| November 2008| Page o2162

doi:10.1107/S1600536808033746

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

N,N′-Bis(2-hy­droxy­ethyl)-N,N′-[ethyl­ene­di­oxy­bis­(o-phenyl­ene­methyl­ene)]­di­ammonium fumarate tetra­hydrate

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Experimental

Crystal data

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Acknowledgements

References

organic compounds

N,N′-Bis(2-hydroxyethyl)-N,N′-[ethylenedioxybis(o-phenylenemethylene)]diammonium fumarate tetrahydrate