Ethane-1,2-diaminium 2,2′-[tereph­thal­oyl­bis(aza­nedi­yl)]di­acetate tetrahydrate

Pook, N.-P.; Gjikaj, M.; Adam, A.

doi:10.1107/S1600536813029632

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page o1731

doi:10.1107/S1600536813029632

Open

access

Ethane-1,2-diaminium 2,2′-[terephthaloylbis(azanediyl)]diacetate tetrahydrate

Niels-Patrick Pook,^a Mimoza Gjikaj ^a and Arnold Adam ^a ^*

^aInstitute of Inorganic and Analytical Chemistry, Clausthal University of Technology, Paul-Ernst-Str. 4, D-38678, Clausthal-Zellerfeld, Germany
^*Correspondence e-mail: arnold.adam@tu-clausthal.de

(Received 15 October 2013; accepted 28 October 2013; online 6 November 2013)

In the title salt hydrate, C₂H₁₀N₂²⁺·C₁₂H₁₀N₂O₆²⁻·4H₂O, each of the ions is located about a centre of inversion and the asymmetric unit is completed by two water molecules in general positons. In the crystal, the cations, anions and water molecules are connected by O—H⋯O and N—H⋯O hydrogen bonding into a three-dimensional network.

CCDC reference: 968970

Related literature

The starting material, 2,2′-(benzene-1,4-dicarboxamido)diacetatic acid, was prepared by the method of Cleaver & Pratt (1955 ). For related organic structures, see: Armelin et al. (2001 ); Ray et al. (2006 ). For crystal strucutres of d-block elements with 2,2′-(terephthaloylbis(azanediyl))diacetate and similar ligands, see: Duan et al. (2010 ); Kostakis et al. (2005 , 2011 ); Wisser et al. (2008 ); Zhang & You (2005); Zhang et al. (2006 ).

Experimental

Crystal data

C₂H₁₀N₂²⁺·C₁₂H₁₀N₂O₆²⁻·4H₂O
M_r = 412.40
Monoclinic, P 2₁ /c
a = 7.3710 (11) Å
b = 9.0675 (11) Å
c = 14.704 (2) Å
β = 105.041 (11)°
V = 949.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 223 K
0.28 × 0.25 × 0.22 mm

Data collection

Stoe IPDS 2 diffractometer
9883 measured reflections
1859 independent reflections
1633 reflections with I > 2σ(I)
R_int = 0.099

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.096
S = 1.09
1859 reflections
183 parameters
All H-atom parameters refined
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4B⋯O3	0.89 (3)	1.80 (3)	2.6792 (16)	169 (2)
N2—H2B⋯O3	0.96 (2)	1.85 (2)	2.7896 (17)	164.3 (18)
O4—H4A⋯O1ⁱ	0.87 (3)	2.03 (3)	2.8741 (16)	162 (2)
O5—H5A⋯O2ⁱⁱ	0.92 (3)	1.87 (3)	2.7669 (17)	168 (2)
O5—H5B⋯O1ⁱⁱⁱ	0.86 (3)	2.01 (3)	2.8641 (17)	169 (3)
N1—H1⋯O4^iv	0.87 (2)	2.02 (2)	2.8509 (17)	159.8 (18)
N2—H2A⋯O5^v	0.93 (2)	1.91 (2)	2.8278 (18)	172.6 (18)
N2—H2C⋯O2^vi	0.93 (2)	1.89 (2)	2.8086 (17)	169 (2)
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) x-1, y, z; (v) -x+2, -y+1, -z+1; (vi) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe, 2008 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia 2012 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 968970

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813029632/nc2319sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813029632/nc2319Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813029632/nc2319Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536813029632/nc2319Isup4.cml

checkCIF report

Comment top

Recently, the interest in constructing metal-organic coordination polymers continuously rises due to their facinating structures and properties with potential application as functional materials. For the synthesis of such compounds frequently relatively rigid ligands with several coordination centers are used. In this context the title compound was prepared, which should be used as a precursor in the synthesis of new coordination polymers.

The crystal structure of the title compound consists of 2,2'-(terephthaloylbis(azanediyl))diacetate anions that are located on centers of inversion as well as of ethylenediaminium cations and water molecules in general positions (Fig. 1). The ethylenediamine cations are connected to the anions by N—H···O hydrogen bonding between the carboxylate O atom and the ammonium H atoms. The anions and cations are additionally linked to water molecules via N—H···O and O—H···O hydrogen bonding into a three-dimensional network (Fig. 2 and Table 1). Furthermore, the compound shows luminescence under excitation with ultraviolet light.

Experimental top

The starting material, 2,2'-(benzene-1,4-dicarboxamido)diacetatic acid, was prepared by the method of Cleaver & Pratt (Cleaver & Pratt, 1955). Single crystals were obtained by slow evaporation from an aqueous solution (40 ml) of 2,2'-terephthaloylbis-(glycine) dihydrate (630 mg) and ethylenediamine (3 ml) at room temperature. Colorless block shaped crystals appeared after a few days.

Refinement top

All hydrogen atoms were located the difference Fourier map and were refined isotropically with no restraints.

Related literature top

For related organic structures, see: Armelin et al. (2001); Ray et al. (2006). For crystal strucutres of d-block elements with 2,2'-(terephthaloylbis(azanediyl))diacetate and similar ligands, see: Duan et al. (2010); Kostakis et al. (2005, 2011); Wisser et al. (2008); Zhang & You (2005); Zhang et al. (2006). The starting material, 2,2'-(benzene-1,4-dicarboxamido)diacetatic acid, was prepared by the method of Cleaver & Pratt (1955).

Computing details top

Data collection: X-AREA (Stoe, 2008); cell refinement: X-AREA (Stoe, 2008); data reduction: X-AREA (Stoe, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. View of the asymmetric unit of the title compound with labeling and displacement ellipsoids drawn at the 50% probability level. The dashed lines indicate N—H···O and O—H···O hydrogen bonds (see Table 1 for details). Symmetry codes: (i) -x - 1, -y - 1, -1 - z; (ii) -x + 1, -y - 1, -z.
	Fig. 2. Crystal structure of the title compound viewed along the a axis. Displacement ellipsoids are drawn at the 50% probability level and hydrogen bonding is shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

Ethane-1,2-diaminium 2,2'-[terephthaloylbis(azanediyl)]diacetate tetrahydrate top

Crystal data top

C₂H₁₀N₂²⁺·C₁₂H₁₀N₂O₆²⁻·4H₂O	F(000) = 440
M_r = 412.40	D_x = 1.443 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1859 reflections
a = 7.3710 (11) Å	θ = 1.0–26.0°
b = 9.0675 (11) Å	µ = 0.12 mm⁻¹
c = 14.704 (2) Å	T = 223 K
β = 105.041 (11)°	Block, colorless
V = 949.1 (2) Å³	0.28 × 0.25 × 0.22 mm
Z = 2

Data collection top

Stoe IPDS 2 diffractometer	1633 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.099
Graphite monochromator	θ_max = 26.0°, θ_min = 2.7°
ω–scans	h = −9→9
9883 measured reflections	k = −11→11
1859 independent reflections	l = −18→18

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	All H-atom parameters refined
S = 1.09	w = 1/[σ²(F_o²) + (0.0383P)² + 0.2529P] where P = (F_o² + 2F_c²)/3
1859 reflections	(Δ/σ)_max < 0.001
183 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂H₁₀N₂²⁺·C₁₂H₁₀N₂O₆²⁻·4H₂O	V = 949.1 (2) Å³
M_r = 412.40	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3710 (11) Å	µ = 0.12 mm⁻¹
b = 9.0675 (11) Å	T = 223 K
c = 14.704 (2) Å	0.28 × 0.25 × 0.22 mm
β = 105.041 (11)°

Data collection top

Stoe IPDS 2 diffractometer	1633 reflections with I > 2σ(I)
9883 measured reflections	R_int = 0.099
1859 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.096	All H-atom parameters refined
S = 1.09	Δρ_max = 0.27 e Å⁻³
1859 reflections	Δρ_min = −0.27 e Å⁻³
183 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	0.49836 (13)	0.43561 (11)	0.11941 (7)	0.0248 (2)
O2	0.67537 (15)	0.79044 (11)	0.17064 (7)	0.0293 (3)
O3	0.87997 (14)	0.70796 (12)	0.30002 (8)	0.0307 (3)
O4	1.16417 (16)	0.83739 (12)	0.24811 (9)	0.0304 (3)
H4A	1.250 (3)	0.875 (3)	0.2948 (17)	0.052 (6)*
H4B	1.067 (3)	0.806 (3)	0.2678 (16)	0.050 (6)*
O5	0.57247 (18)	0.30272 (13)	0.50636 (9)	0.0387 (3)
H5A	0.505 (3)	0.294 (3)	0.4449 (19)	0.058 (7)*
H5B	0.539 (4)	0.227 (3)	0.534 (2)	0.073 (8)*
N1	0.39210 (16)	0.60948 (13)	0.20250 (8)	0.0216 (3)
H1	0.302 (3)	0.670 (2)	0.2048 (14)	0.037 (5)*
N2	1.13211 (18)	0.50461 (14)	0.40607 (9)	0.0256 (3)
H2A	1.234 (3)	0.561 (2)	0.4374 (14)	0.035 (5)*
H2B	1.039 (3)	0.560 (2)	0.3615 (15)	0.041 (5)*
H2C	1.183 (3)	0.434 (3)	0.3741 (16)	0.053 (6)*
C1	0.17640 (18)	0.50869 (14)	0.06420 (9)	0.0192 (3)
C2	0.01507 (19)	0.54693 (15)	0.09178 (10)	0.0218 (3)
H2	0.023 (2)	0.5766 (19)	0.1573 (13)	0.028 (4)*
C3	0.16018 (19)	0.46137 (15)	−0.02754 (10)	0.0220 (3)
H3	0.268 (2)	0.4371 (18)	−0.0461 (12)	0.021 (4)*
C4	0.36832 (18)	0.51552 (14)	0.13090 (9)	0.0194 (3)
C5	0.56927 (18)	0.62239 (15)	0.27321 (10)	0.0215 (3)
H51	0.625 (2)	0.527 (2)	0.2943 (12)	0.025 (4)*
H52	0.544 (3)	0.673 (2)	0.3279 (14)	0.033 (5)*
C6	0.71953 (19)	0.71403 (14)	0.24383 (10)	0.0205 (3)
C7	1.0404 (2)	0.43916 (16)	0.47572 (11)	0.0275 (3)
H7A	1.135 (3)	0.384 (2)	0.5210 (14)	0.036 (5)*
H7B	0.937 (3)	0.375 (2)	0.4412 (13)	0.033 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0196 (5)	0.0265 (5)	0.0275 (5)	0.0040 (4)	0.0048 (4)	−0.0023 (4)
O2	0.0294 (6)	0.0305 (5)	0.0258 (6)	−0.0051 (4)	0.0034 (4)	0.0053 (4)
O3	0.0208 (5)	0.0308 (6)	0.0363 (6)	−0.0048 (4)	−0.0001 (4)	0.0053 (4)
O4	0.0237 (6)	0.0322 (6)	0.0349 (6)	−0.0038 (4)	0.0070 (5)	−0.0053 (5)
O5	0.0466 (7)	0.0325 (6)	0.0307 (7)	−0.0133 (5)	−0.0010 (5)	0.0009 (5)
N1	0.0157 (5)	0.0219 (6)	0.0266 (6)	0.0004 (4)	0.0041 (5)	−0.0026 (4)
N2	0.0255 (6)	0.0263 (6)	0.0237 (6)	0.0008 (5)	0.0040 (5)	−0.0018 (5)
C1	0.0180 (6)	0.0154 (6)	0.0237 (7)	−0.0017 (5)	0.0047 (5)	0.0024 (5)
C2	0.0204 (7)	0.0224 (7)	0.0230 (7)	−0.0017 (5)	0.0065 (5)	−0.0016 (5)
C3	0.0170 (6)	0.0226 (7)	0.0281 (7)	−0.0007 (5)	0.0087 (5)	−0.0016 (5)
C4	0.0189 (6)	0.0177 (6)	0.0227 (7)	−0.0011 (5)	0.0070 (5)	0.0033 (5)
C5	0.0201 (7)	0.0229 (7)	0.0204 (7)	−0.0011 (5)	0.0033 (5)	−0.0010 (6)
C6	0.0202 (7)	0.0181 (6)	0.0228 (7)	−0.0006 (5)	0.0050 (5)	−0.0038 (5)
C7	0.0358 (8)	0.0206 (7)	0.0260 (8)	0.0025 (6)	0.0076 (6)	−0.0010 (6)

Geometric parameters (Å, º) top

O1—C4	1.2476 (16)	C1—C3	1.391 (2)
O2—C6	1.2500 (18)	C1—C2	1.3961 (19)
O3—C6	1.2558 (17)	C1—C4	1.4990 (18)
O4—H4A	0.87 (3)	C2—C3ⁱ	1.390 (2)
O4—H4B	0.89 (3)	C2—H2	0.987 (19)
O5—H5A	0.92 (3)	C3—C2ⁱ	1.390 (2)
O5—H5B	0.86 (3)	C3—H3	0.931 (17)
N1—C4	1.3301 (18)	C5—C6	1.5337 (18)
N1—C5	1.4476 (17)	C5—H51	0.977 (18)
N1—H1	0.87 (2)	C5—H52	0.98 (2)
N2—C7	1.489 (2)	C6—O3	1.2558 (17)
N2—H2A	0.93 (2)	C7—C7ⁱⁱ	1.517 (3)
N2—H2B	0.96 (2)	C7—H7A	0.97 (2)
N2—H2C	0.93 (2)	C7—H7B	0.98 (2)

H4A—O4—H4B	110 (2)	O1—C4—N1	122.09 (12)
H5A—O5—H5B	104 (2)	O1—C4—C1	121.01 (12)
C4—N1—C5	121.96 (12)	N1—C4—C1	116.90 (11)
C4—N1—H1	119.3 (13)	N1—C5—C6	115.11 (12)
C5—N1—H1	118.6 (13)	N1—C5—H51	112.5 (10)
C7—N2—H2A	109.4 (12)	C6—C5—H51	107.3 (10)
C7—N2—H2B	108.1 (12)	N1—C5—H52	107.5 (11)
H2A—N2—H2B	113.2 (17)	C6—C5—H52	106.3 (11)
C7—N2—H2C	112.9 (14)	H51—C5—H52	107.8 (15)
H2A—N2—H2C	104.4 (18)	O2—C6—O3	125.53 (13)
H2B—N2—H2C	108.9 (18)	O2—C6—O3	125.53 (13)
C3—C1—C2	119.54 (13)	O2—C6—C5	119.81 (12)
C3—C1—C4	118.45 (12)	O3—C6—C5	114.62 (12)
C2—C1—C4	122.01 (13)	O3—C6—C5	114.62 (12)
C3ⁱ—C2—C1	120.03 (14)	N2—C7—C7ⁱⁱ	109.72 (15)
C3ⁱ—C2—H2	119.1 (10)	N2—C7—H7A	107.8 (12)
C1—C2—H2	120.9 (10)	C7ⁱⁱ—C7—H7A	110.7 (12)
C2ⁱ—C3—C1	120.43 (13)	N2—C7—H7B	107.9 (11)
C2ⁱ—C3—H3	120.1 (10)	C7ⁱⁱ—C7—H7B	109.0 (11)
C1—C3—H3	119.5 (10)	H7A—C7—H7B	111.6 (16)

C3—C1—C2—C3ⁱ	−0.5 (2)	C3—C1—C4—N1	154.93 (12)
C4—C1—C2—C3ⁱ	−179.87 (12)	C2—C1—C4—N1	−25.66 (18)
C2—C1—C3—C2ⁱ	0.5 (2)	C4—N1—C5—C6	79.20 (16)
C4—C1—C3—C2ⁱ	179.89 (12)	O3—O3—C6—O2	0.00 (17)
C5—N1—C4—O1	−1.6 (2)	O3—O3—C6—C5	0.00 (13)
C5—N1—C4—C1	177.93 (11)	N1—C5—C6—O2	11.70 (18)
C3—C1—C4—O1	−25.48 (18)	N1—C5—C6—O3	−170.64 (12)
C2—C1—C4—O1	153.92 (13)	N1—C5—C6—O3	−170.64 (12)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···O3	0.89 (3)	1.80 (3)	2.6792 (16)	169 (2)
N2—H2B···O3	0.96 (2)	1.85 (2)	2.7896 (17)	164.3 (18)
O4—H4A···O1ⁱⁱⁱ	0.87 (3)	2.03 (3)	2.8741 (16)	162 (2)
O5—H5A···O2^iv	0.92 (3)	1.87 (3)	2.7669 (17)	168 (2)
O5—H5B···O1^v	0.86 (3)	2.01 (3)	2.8641 (17)	169 (3)
N1—H1···O4^vi	0.87 (2)	2.02 (2)	2.8509 (17)	159.8 (18)
N2—H2A···O5ⁱⁱ	0.93 (2)	1.91 (2)	2.8278 (18)	172.6 (18)
N2—H2C···O2^vii	0.93 (2)	1.89 (2)	2.8086 (17)	169 (2)

Symmetry codes: (ii) −x+2, −y+1, −z+1; (iii) −x+2, y+1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2; (vi) x−1, y, z; (vii) −x+2, 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—H4B···O3	0.89 (3)	1.80 (3)	2.6792 (16)	169 (2)
N2—H2B···O3	0.96 (2)	1.85 (2)	2.7896 (17)	164.3 (18)
O4—H4A···O1ⁱ	0.87 (3)	2.03 (3)	2.8741 (16)	162 (2)
O5—H5A···O2ⁱⁱ	0.92 (3)	1.87 (3)	2.7669 (17)	168 (2)
O5—H5B···O1ⁱⁱⁱ	0.86 (3)	2.01 (3)	2.8641 (17)	169 (3)
N1—H1···O4^iv	0.87 (2)	2.02 (2)	2.8509 (17)	159.8 (18)
N2—H2A···O5^v	0.93 (2)	1.91 (2)	2.8278 (18)	172.6 (18)
N2—H2C···O2^vi	0.93 (2)	1.89 (2)	2.8086 (17)	169 (2)

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

References

Armelin, E., Escudero, E., Campos, L. & Puiggalí, J. (2001). Acta Cryst. C57, 172–173. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Cleaver, C. S. & Pratt, B. C. (1955). J. Am. Chem. Soc. 77, 1544–1546. CrossRef CAS Web of Science Google Scholar
Duan, J., Zheng, B., Bai, J., Zhang, Q. & Zuo, C. (2010). Inorg. Chim. Acta, 363, 3172–3177. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kostakis, G. E., Casella, L., Boudalis, A. K., Monzani, E. & Plakatouras, J. C. (2011). New J. Chem. 35, 1060–1071. Web of Science CSD CrossRef CAS Google Scholar
Kostakis, G. E., Casella, L., Hadjiliadis, N., Monzani, E., Kourkoumelis, N. & Plakatouras, J. C. (2005). Chem. Commun. 30, 3859–3861. Web of Science CSD CrossRef Google Scholar
Ray, S., Hegde, R. P., Das, A. K., Shamala, N. & Banerjee, A. (2006). Tetrahedron, 62, 9603–9609. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe (2008). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wisser, B., Chamayou, A.-C., Miller, R., Scherer, W. & Janiak, C. (2008). CrystEngComm, 10, 461–464. Web of Science CSD CrossRef CAS Google Scholar
Zhang, H.-T., Li, Y.-Z., Wang, T.-W., Nfor, E. N., Wang, H.-Q. & You, X.-Z. (2006). Eur. J. Inorg. Chem. pp. 3532–3536. Web of Science CSD CrossRef Google Scholar
Zhang, H.-T. & You, X.-Z. (2005). Acta Cryst. E61, m1163–m1165. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page o1731

doi:10.1107/S1600536813029632

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Ethane-1,2-diaminium 2,2′-[tereph­thal­oyl­bis­(aza­nedi­yl)]di­acetate tetrahydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

Ethane-1,2-diaminium 2,2′-[terephthaloylbis(azanediyl)]diacetate tetrahydrate