Bis(ethyl­enediammonium) benzene-1,2,4,5-tetra­carboxyl­ate dihydrate

The asymmetric unit of the title compound, 2C₂H₁₀N₂²⁺·C₁₀H₂O₈⁴⁻·2H₂O, contains one cation, one half-anion and one water mol­ecule; the anion is centrosymmetric. Inter­molecular N—H...O and O—H...O hydrogen bonds seem to be effective in the stabilization of the crystal structure, resulting in the formation of a supra­molecular structure.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.045
• wR factor = 0.102
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis(ethylenediammonium) benzene-1,2,4,5-tetracarboxylate dihydrate

Crystal data

2C2H10N2^2+·C10H2O8^4^−·2H2O	Z = 1
Mr = 410.39	F(000) = 218
Triclinic, P1	Dx = 1.474 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4283 (9) Å	Cell parameters from 212 reflections
b = 8.3936 (12) Å	θ = 3–26°
c = 9.8926 (13) Å	µ = 0.13 mm^−1
α = 112.393 (5)°	T = 120 K
β = 105.710 (5)°	Prism, colorless
γ = 95.883 (5)°	0.15 × 0.13 × 0.11 mm
V = 462.23 (11) Å^3

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	1768 independent reflections
Radiation source: fine-focus sealed tube	1414 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −6→7
Tmin = 0.978, Tmax = 0.988	k = −10→9
2724 measured reflections	l = −11→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: mixed
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.03P)^2 + 0.5P] where P = (Fo^2 + 2Fc^2)/3
1768 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.3231 (2)	0.77805 (18)	0.91049 (15)	0.0155 (3)
O2	0.0527 (2)	0.57855 (18)	0.90110 (15)	0.0153 (3)
O3	0.4297 (2)	0.42522 (18)	0.78907 (15)	0.0147 (3)
O4	0.4685 (2)	0.28485 (19)	0.55869 (16)	0.0201 (3)
C1	−0.1010 (3)	0.6136 (2)	0.5895 (2)	0.0122 (4)
H1A	−0.1705	0.6915	0.6512	0.015*
C2	0.0814 (3)	0.5635 (2)	0.6623 (2)	0.0112 (4)
C3	0.1841 (3)	0.4477 (2)	0.5715 (2)	0.0111 (4)
C4	0.1620 (3)	0.6440 (2)	0.8383 (2)	0.0116 (4)
C5	0.3764 (3)	0.3820 (2)	0.6451 (2)	0.0125 (4)
N1	−0.2420 (3)	0.1955 (2)	0.77257 (18)	0.0145 (4)
H1B	−0.3345	0.2272	0.7047	0.017*
H1C	−0.1785	0.2913	0.8659	0.017*
H1D	−0.3208	0.1087	0.7848	0.017*
N2	0.2596 (3)	0.2813 (2)	0.95610 (19)	0.0156 (4)
H2A	0.3827	0.2641	1.0154	0.019*
H2B	0.1799	0.3345	1.0165	0.019*
H2C	0.3012	0.3516	0.9126	0.019*
C6	−0.0654 (3)	0.1291 (3)	0.7110 (2)	0.0153 (4)
H6A	−0.0022	0.2129	0.6763	0.018*
H6B	−0.1323	0.0135	0.6196	0.018*
C7	0.1203 (3)	0.1073 (3)	0.8312 (2)	0.0178 (4)
H7A	0.0552	0.0388	0.8781	0.021*
H7B	0.2153	0.0394	0.7792	0.021*
O1S	0.4478 (3)	0.1235 (2)	0.25264 (17)	0.0274 (4)
H1S	0.5213	0.1603	0.2101	0.033*
H2S	0.4803	0.1909	0.3446	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0142 (7)	0.0166 (7)	0.0140 (7)	0.0029 (6)	0.0028 (6)	0.0063 (6)
O2	0.0162 (7)	0.0189 (7)	0.0141 (7)	0.0053 (6)	0.0070 (6)	0.0086 (6)
O3	0.0147 (7)	0.0194 (7)	0.0119 (7)	0.0071 (6)	0.0043 (5)	0.0078 (6)
O4	0.0213 (8)	0.0282 (8)	0.0148 (7)	0.0167 (6)	0.0074 (6)	0.0094 (6)
C1	0.0117 (9)	0.0127 (9)	0.0139 (9)	0.0043 (7)	0.0063 (7)	0.0058 (7)
C2	0.0111 (9)	0.0125 (9)	0.0116 (9)	0.0019 (7)	0.0042 (7)	0.0066 (7)
C3	0.0099 (9)	0.0125 (9)	0.0133 (9)	0.0027 (7)	0.0040 (7)	0.0079 (7)
C4	0.0104 (9)	0.0141 (9)	0.0132 (9)	0.0090 (7)	0.0043 (7)	0.0072 (8)
C5	0.0109 (9)	0.0125 (9)	0.0145 (9)	0.0027 (7)	0.0036 (7)	0.0065 (8)
N1	0.0117 (8)	0.0162 (9)	0.0157 (8)	0.0046 (6)	0.0038 (7)	0.0071 (7)
N2	0.0112 (8)	0.0198 (9)	0.0172 (8)	0.0043 (7)	0.0034 (7)	0.0102 (7)
C6	0.0150 (10)	0.0151 (10)	0.0152 (9)	0.0050 (8)	0.0060 (8)	0.0049 (8)
C7	0.0140 (10)	0.0159 (10)	0.0232 (11)	0.0068 (8)	0.0063 (8)	0.0073 (8)
O1S	0.0363 (10)	0.0214 (8)	0.0214 (8)	−0.0028 (7)	0.0179 (7)	0.0027 (6)

Geometric parameters (Å, º)

O1—C4	1.264 (2)	N1—H1C	0.9100
O2—C4	1.264 (2)	N1—H1D	0.9100
O3—C5	1.263 (2)	N2—C7	1.490 (3)
O4—C5	1.260 (2)	N2—H2A	0.9100
C1—C2	1.395 (3)	N2—H2B	0.9100
C1—C3^i	1.395 (3)	N2—H2C	0.9100
C1—H1A	0.9500	C6—C7	1.521 (3)
C2—C3	1.405 (3)	C6—H6A	0.9900
C2—C4	1.516 (2)	C6—H6B	0.9900
C3—C1^i	1.395 (3)	C7—H7A	0.9900
C3—C5	1.523 (3)	C7—H7B	0.9900
N1—C6	1.488 (2)	O1S—H1S	0.8200
N1—H1B	0.9100	O1S—H2S	0.8200
C2—C1—C3^i	121.68 (18)	H1C—N1—H1D	109.5
C2—C1—H1A	119.2	C7—N2—H2A	109.5
C3^i—C1—H1A	119.2	C7—N2—H2B	109.5
C1—C2—C3	119.34 (17)	H2A—N2—H2B	109.5
C1—C2—C4	116.92 (17)	C7—N2—H2C	109.5
C3—C2—C4	123.71 (17)	H2A—N2—H2C	109.5
C1^i—C3—C2	118.98 (17)	H2B—N2—H2C	109.5
C1^i—C3—C5	119.73 (17)	N1—C6—C7	112.46 (16)
C2—C3—C5	121.24 (17)	N1—C6—H6A	109.1
O2—C4—O1	125.07 (17)	C7—C6—H6A	109.1
O2—C4—C2	117.09 (16)	N1—C6—H6B	109.1
O1—C4—C2	117.66 (16)	C7—C6—H6B	109.1
O4—C5—O3	124.09 (18)	H6A—C6—H6B	107.8
O4—C5—C3	118.39 (16)	N2—C7—C6	111.91 (16)
O3—C5—C3	117.50 (17)	N2—C7—H7A	109.2
C6—N1—H1B	109.5	C6—C7—H7A	109.2
C6—N1—H1C	109.5	N2—C7—H7B	109.2
H1B—N1—H1C	109.5	C6—C7—H7B	109.2
C6—N1—H1D	109.5	H7A—C7—H7B	107.9
H1B—N1—H1D	109.5	H1S—O1S—H2S	112.0
C3^i—C1—C2—C3	−0.3 (3)	C1—C2—C4—O1	−97.1 (2)
C3^i—C1—C2—C4	177.78 (17)	C3—C2—C4—O1	80.9 (2)
C1—C2—C3—C1^i	0.3 (3)	C1^i—C3—C5—O4	6.0 (3)
C4—C2—C3—C1^i	−177.65 (17)	C2—C3—C5—O4	−176.78 (17)
C1—C2—C3—C5	−176.92 (17)	C1^i—C3—C5—O3	−172.26 (17)
C4—C2—C3—C5	5.2 (3)	C2—C3—C5—O3	4.9 (3)
C1—C2—C4—O2	78.3 (2)	N1—C6—C7—N2	−71.1 (2)
C3—C2—C4—O2	−103.7 (2)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3^ii	0.91	2.43	2.997 (2)	121
N1—H1B···O4^ii	0.91	1.90	2.805 (2)	178
N1—H1C···O2^iii	0.91	2.01	2.869 (2)	156
N1—H1D···O1S^iv	0.91	1.89	2.751 (3)	158
O1S—H1S···O1^v	0.82	1.92	2.740 (2)	173
N2—H2A···O1^vi	0.91	1.96	2.836 (2)	162
N2—H2A···O3^vi	0.91	2.50	2.819 (2)	101
N2—H2B···O2^iii	0.91	1.97	2.857 (2)	166
N2—H2C···O3	0.91	1.89	2.759 (2)	159
O1S—H2S···O4	0.82	1.98	2.764 (2)	158

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