Ethane-1,2-diaminium 2,2'-[tereph-thal-oyl-bis(aza-nedi-yl)]di-acetate tetrahydrate.

In the title salt hydrate, C2H10N2 (2+)·C12H10N2O6 (2-)·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 mol-ecules are connected by O-H⋯O and N-H⋯O hydrogen bonding into a three-dimensional network.

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

C2H10N2 2+·C12H10N2O6 2−·4H2O

M = 412.40

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.096

S = 1.09

1859 reflections

183 parameters

All H-atom parameters refined

Δρmax = 0.27 e Å−3

Δρmin = −0.27 e Å−3

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 ▶).

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

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813029632/nc2319Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813029632/nc2319Isup4.cml

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

C2H10N22+·C12H10N2O62−·4H2O	F(000) = 440
Mr = 412.40	Dx = 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

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

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(Fo2) + (0.0383P)2 + 0.2529P] where P = (Fo2 + 2Fc2)/3
1859 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.27 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	0.49836 (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)*

	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)

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)

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···O2iv	0.92 (3)	1.87 (3)	2.7669 (17)	168 (2)
O5—H5B···O1v	0.86 (3)	2.01 (3)	2.8641 (17)	169 (3)
N1—H1···O4vi	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···O2vii	0.93 (2)	1.89 (2)	2.8086 (17)	169 (2)

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⋯O4iv	0.87 (2)	2.02 (2)	2.8509 (17)	159.8 (18)
N2—H2A⋯O5v	0.93 (2)	1.91 (2)	2.8278 (18)	172.6 (18)
N2—H2C⋯O2vi	0.93 (2)	1.89 (2)	2.8086 (17)	169 (2)

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