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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806041481/hk2148sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806041481/hk2148Isup2.hkl
Contains datablock I

CCDC reference: 617701

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

No syntax errors found


No errors found in this datablock

Computing details top

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 top
Crystal data top
2C2H10N22+·C10H2O84·2H2OZ = 1
Mr = 410.39F(000) = 218
Triclinic, P1Dx = 1.474 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.4283 (9) ÅCell parameters from 212 reflections
b = 8.3936 (12) Åθ = 3–26°
c = 9.8926 (13) ŵ = 0.13 mm1
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) Å3
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1768 independent reflections
Radiation source: fine-focus sealed tube1414 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
φ and ω scansθmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
h = 67
Tmin = 0.978, Tmax = 0.988k = 109
2724 measured reflectionsl = 1112
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: mixed
wR(F2) = 0.102H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.03P)2 + 0.5P]
where P = (Fo2 + 2Fc2)/3
1768 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.31 e Å3
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
xyzUiso*/Ueq
O10.3231 (2)0.77805 (18)0.91049 (15)0.0155 (3)
O20.0527 (2)0.57855 (18)0.90110 (15)0.0153 (3)
O30.4297 (2)0.42522 (18)0.78907 (15)0.0147 (3)
O40.4685 (2)0.28485 (19)0.55869 (16)0.0201 (3)
C10.1010 (3)0.6136 (2)0.5895 (2)0.0122 (4)
H1A0.17050.69150.65120.015*
C20.0814 (3)0.5635 (2)0.6623 (2)0.0112 (4)
C30.1841 (3)0.4477 (2)0.5715 (2)0.0111 (4)
C40.1620 (3)0.6440 (2)0.8383 (2)0.0116 (4)
C50.3764 (3)0.3820 (2)0.6451 (2)0.0125 (4)
N10.2420 (3)0.1955 (2)0.77257 (18)0.0145 (4)
H1B0.33450.22720.70470.017*
H1C0.17850.29130.86590.017*
H1D0.32080.10870.78480.017*
N20.2596 (3)0.2813 (2)0.95610 (19)0.0156 (4)
H2A0.38270.26411.01540.019*
H2B0.17990.33451.01650.019*
H2C0.30120.35160.91260.019*
C60.0654 (3)0.1291 (3)0.7110 (2)0.0153 (4)
H6A0.00220.21290.67630.018*
H6B0.13230.01350.61960.018*
C70.1203 (3)0.1073 (3)0.8312 (2)0.0178 (4)
H7A0.05520.03880.87810.021*
H7B0.21530.03940.77920.021*
O1S0.4478 (3)0.1235 (2)0.25264 (17)0.0274 (4)
H1S0.52130.16030.21010.033*
H2S0.48030.19090.34460.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0142 (7)0.0166 (7)0.0140 (7)0.0029 (6)0.0028 (6)0.0063 (6)
O20.0162 (7)0.0189 (7)0.0141 (7)0.0053 (6)0.0070 (6)0.0086 (6)
O30.0147 (7)0.0194 (7)0.0119 (7)0.0071 (6)0.0043 (5)0.0078 (6)
O40.0213 (8)0.0282 (8)0.0148 (7)0.0167 (6)0.0074 (6)0.0094 (6)
C10.0117 (9)0.0127 (9)0.0139 (9)0.0043 (7)0.0063 (7)0.0058 (7)
C20.0111 (9)0.0125 (9)0.0116 (9)0.0019 (7)0.0042 (7)0.0066 (7)
C30.0099 (9)0.0125 (9)0.0133 (9)0.0027 (7)0.0040 (7)0.0079 (7)
C40.0104 (9)0.0141 (9)0.0132 (9)0.0090 (7)0.0043 (7)0.0072 (8)
C50.0109 (9)0.0125 (9)0.0145 (9)0.0027 (7)0.0036 (7)0.0065 (8)
N10.0117 (8)0.0162 (9)0.0157 (8)0.0046 (6)0.0038 (7)0.0071 (7)
N20.0112 (8)0.0198 (9)0.0172 (8)0.0043 (7)0.0034 (7)0.0102 (7)
C60.0150 (10)0.0151 (10)0.0152 (9)0.0050 (8)0.0060 (8)0.0049 (8)
C70.0140 (10)0.0159 (10)0.0232 (11)0.0068 (8)0.0063 (8)0.0073 (8)
O1S0.0363 (10)0.0214 (8)0.0214 (8)0.0028 (7)0.0179 (7)0.0027 (6)
Geometric parameters (Å, º) top
O1—C41.264 (2)N1—H1C0.9100
O2—C41.264 (2)N1—H1D0.9100
O3—C51.263 (2)N2—C71.490 (3)
O4—C51.260 (2)N2—H2A0.9100
C1—C21.395 (3)N2—H2B0.9100
C1—C3i1.395 (3)N2—H2C0.9100
C1—H1A0.9500C6—C71.521 (3)
C2—C31.405 (3)C6—H6A0.9900
C2—C41.516 (2)C6—H6B0.9900
C3—C1i1.395 (3)C7—H7A0.9900
C3—C51.523 (3)C7—H7B0.9900
N1—C61.488 (2)O1S—H1S0.8200
N1—H1B0.9100O1S—H2S0.8200
C2—C1—C3i121.68 (18)H1C—N1—H1D109.5
C2—C1—H1A119.2C7—N2—H2A109.5
C3i—C1—H1A119.2C7—N2—H2B109.5
C1—C2—C3119.34 (17)H2A—N2—H2B109.5
C1—C2—C4116.92 (17)C7—N2—H2C109.5
C3—C2—C4123.71 (17)H2A—N2—H2C109.5
C1i—C3—C2118.98 (17)H2B—N2—H2C109.5
C1i—C3—C5119.73 (17)N1—C6—C7112.46 (16)
C2—C3—C5121.24 (17)N1—C6—H6A109.1
O2—C4—O1125.07 (17)C7—C6—H6A109.1
O2—C4—C2117.09 (16)N1—C6—H6B109.1
O1—C4—C2117.66 (16)C7—C6—H6B109.1
O4—C5—O3124.09 (18)H6A—C6—H6B107.8
O4—C5—C3118.39 (16)N2—C7—C6111.91 (16)
O3—C5—C3117.50 (17)N2—C7—H7A109.2
C6—N1—H1B109.5C6—C7—H7A109.2
C6—N1—H1C109.5N2—C7—H7B109.2
H1B—N1—H1C109.5C6—C7—H7B109.2
C6—N1—H1D109.5H7A—C7—H7B107.9
H1B—N1—H1D109.5H1S—O1S—H2S112.0
C3i—C1—C2—C30.3 (3)C1—C2—C4—O197.1 (2)
C3i—C1—C2—C4177.78 (17)C3—C2—C4—O180.9 (2)
C1—C2—C3—C1i0.3 (3)C1i—C3—C5—O46.0 (3)
C4—C2—C3—C1i177.65 (17)C2—C3—C5—O4176.78 (17)
C1—C2—C3—C5176.92 (17)C1i—C3—C5—O3172.26 (17)
C4—C2—C3—C55.2 (3)C2—C3—C5—O34.9 (3)
C1—C2—C4—O278.3 (2)N1—C6—C7—N271.1 (2)
C3—C2—C4—O2103.7 (2)
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O3ii0.912.432.997 (2)121
N1—H1B···O4ii0.911.902.805 (2)178
N1—H1C···O2iii0.912.012.869 (2)156
N1—H1D···O1Siv0.911.892.751 (3)158
O1S—H1S···O1v0.821.922.740 (2)173
N2—H2A···O1vi0.911.962.836 (2)162
N2—H2A···O3vi0.912.502.819 (2)101
N2—H2B···O2iii0.911.972.857 (2)166
N2—H2C···O30.911.892.759 (2)159
O1S—H2S···O40.821.982.764 (2)158
Symmetry codes: (ii) x1, 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.
 

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