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Colourless crystals of the title compound, C2H10N22+·2C10H5O8-·2H2O, were isolated from an aqueous solution. The basic structural unit consists of two trihydrogen 1,2,4,5-benzene­tetra­carboxyl­ate (H3btec-) anions, an ethyl­enediammonium cation and two solvent water mol­ecules. The ethyl­enediammonium cation is centrosymmetric. The anion has a short intra­molecular hydrogen bond of 2.427 (4) Å involving a deprotonated carboxyl­ate group as acceptor. A three-dimensional hydrogen-bonding network defines the crystal packing, and solvent water mol­ecules and the cations occupy voids in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805042741/kp6074sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805042741/kp6074Isup2.hkl
Contains datablock I

CCDC reference: 298485

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.055
  • wR factor = 0.200
  • Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Alert level A DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards. PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.91 PLAT772_ALERT_2_A Suspect O-H Bond in CIF: O3 -H101 .. 1.40 Ang.
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.608 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _diffrn_reflns_theta_full 27.48 From the CIF: _reflns_number_total 2484 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2738 Completeness (_total/calc) 90.72% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.91 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.61 e/A   3 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.60 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT353_ALERT_3_C Long N-H Bond (0.87A) N1 - H201 ... 1.04 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C9 .. 3.00 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C2 H10 N2
3 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 17 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: RAPID AUTO (Rigaku, 1998); cell refinement: RAPID AUTO; data reduction: RAPID AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1993); software used to prepare material for publication: SHELXL97/2 (Sheldrick,1997).

Ethylenediammonium bis(trihydrogen 1,2,4,5-benzenetetracarboxylate) dihydrate top
Crystal data top
C2H10N22+·2C10H5O8·2H2OZ = 1
Mr = 604.44F(000) = 314
Triclinic, P1Dx = 1.687 Mg m3
a = 8.118 (2) ÅMo Kα radiation, λ = 0.71069 Å
b = 8.2266 (17) ÅCell parameters from 2246 reflections
c = 9.596 (3) Åθ = 2.6–27.4°
α = 83.50 (1)°µ = 0.15 mm1
β = 77.178 (13)°T = 293 K
γ = 72.395 (10)°Block, colourless
V = 594.9 (2) Å30.35 × 0.35 × 0.32 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2074 reflections with I > 2σ(I)
Radiation source: rotor targetRint = 0.033
Graphite monochromatorθmax = 27.5°, θmin = 2.6°
Oscillation scansh = 109
4366 measured reflectionsk = 1010
2484 independent reflectionsl = 1212
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)] = 0.055Hydrogen site location: difference Fourier map
wR(F2) = 0.200All H-atom parameters refined
S = 1.01 w = 1/[σ2(Fo2) + (0.0722P)2 + 2.3708P]
where P = (Fo2 + 2Fc2)/3
2484 reflections(Δ/σ)max < 0.001
238 parametersΔρmax = 0.61 e Å3
1 restraintΔρmin = 0.60 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
O50.1685 (3)0.5467 (3)0.0613 (3)0.0324 (6)
O40.4565 (3)0.2125 (4)0.4121 (2)0.0297 (6)
O70.4551 (4)0.1883 (3)0.3199 (3)0.0297 (6)
O10.9117 (3)0.1961 (3)0.0030 (3)0.0328 (6)
O60.2586 (4)0.5046 (3)0.1700 (3)0.0332 (6)
O30.7459 (3)0.1156 (4)0.3598 (3)0.0311 (6)
O20.9242 (3)0.1065 (4)0.1980 (3)0.0328 (6)
O80.6372 (4)0.3513 (4)0.3435 (3)0.0358 (7)
O90.8316 (4)0.0926 (4)0.6035 (4)0.0408 (7)
N11.1091 (4)0.3843 (4)0.5920 (3)0.0281 (7)
H3010.734 (7)0.131 (7)0.617 (6)0.046 (14)*
H2051.124 (6)0.629 (6)0.559 (5)0.036 (12)*
H1060.760 (5)0.022 (5)0.146 (4)0.025 (10)*
H1010.859 (7)0.010 (7)0.267 (6)0.048 (14)*
H1030.372 (6)0.370 (6)0.206 (5)0.032 (11)*
H2040.942 (7)0.533 (7)0.650 (6)0.048 (14)*
H1070.470 (6)0.199 (6)0.421 (5)0.035 (12)*
H1050.084 (9)0.630 (9)0.024 (7)0.09 (2)*
H2011.154 (8)0.408 (7)0.688 (6)0.061 (16)*
H2031.213 (8)0.384 (7)0.516 (6)0.062 (16)*
H2021.026 (8)0.269 (8)0.612 (6)0.059 (16)*
H3020.824 (11)0.014 (11)0.558 (9)0.10 (3)*
C10.7031 (4)0.0632 (4)0.0656 (3)0.0199 (6)
C20.5862 (4)0.1676 (4)0.1699 (3)0.0184 (6)
C30.4467 (4)0.2961 (4)0.1306 (3)0.0201 (6)
C40.4245 (4)0.3285 (4)0.0091 (3)0.0192 (6)
C50.5456 (4)0.2309 (4)0.1147 (3)0.0178 (6)
C60.6800 (4)0.0963 (4)0.0756 (3)0.0205 (6)
C70.8542 (4)0.0901 (4)0.0883 (4)0.0220 (7)
C80.5976 (4)0.1621 (4)0.3257 (3)0.0219 (7)
C90.2745 (4)0.4685 (4)0.0479 (3)0.0207 (6)
C100.5470 (4)0.2663 (4)0.2716 (3)0.0213 (6)
C111.0330 (5)0.5197 (5)0.5689 (4)0.0272 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O50.0288 (13)0.0301 (13)0.0250 (13)0.0122 (11)0.0049 (10)0.0056 (10)
O40.0308 (13)0.0430 (15)0.0141 (11)0.0052 (11)0.0079 (9)0.0042 (10)
O70.0372 (14)0.0373 (14)0.0179 (12)0.0148 (11)0.0076 (10)0.0008 (10)
O10.0281 (13)0.0266 (13)0.0356 (15)0.0064 (10)0.0077 (11)0.0061 (11)
O60.0342 (14)0.0337 (14)0.0229 (13)0.0053 (11)0.0109 (10)0.0029 (10)
O30.0280 (13)0.0405 (15)0.0252 (13)0.0046 (11)0.0131 (10)0.0019 (11)
O20.0256 (12)0.0359 (14)0.0319 (14)0.0040 (11)0.0140 (10)0.0002 (11)
O80.0438 (16)0.0467 (17)0.0208 (13)0.0230 (13)0.0037 (11)0.0047 (11)
O90.0371 (16)0.0384 (17)0.0411 (17)0.0023 (13)0.0096 (13)0.0021 (14)
N10.0307 (15)0.0366 (17)0.0221 (15)0.0135 (14)0.0113 (12)0.0005 (13)
C10.0161 (13)0.0204 (15)0.0218 (15)0.0042 (11)0.0029 (11)0.0004 (12)
C20.0196 (14)0.0194 (14)0.0157 (14)0.0046 (11)0.0053 (11)0.0017 (11)
C30.0204 (14)0.0188 (14)0.0186 (15)0.0026 (12)0.0018 (11)0.0023 (12)
C40.0197 (14)0.0184 (14)0.0177 (15)0.0032 (11)0.0021 (11)0.0022 (11)
C50.0205 (14)0.0189 (14)0.0152 (14)0.0060 (11)0.0039 (11)0.0038 (11)
C60.0195 (14)0.0182 (14)0.0200 (15)0.0017 (12)0.0009 (12)0.0021 (12)
C70.0173 (14)0.0231 (16)0.0237 (16)0.0034 (12)0.0053 (12)0.0021 (12)
C80.0289 (16)0.0221 (15)0.0156 (14)0.0068 (13)0.0072 (12)0.0007 (12)
C90.0211 (14)0.0202 (15)0.0197 (15)0.0034 (12)0.0046 (12)0.0020 (12)
C100.0220 (15)0.0195 (15)0.0175 (15)0.0000 (12)0.0016 (11)0.0020 (11)
C110.0310 (18)0.0309 (18)0.0222 (18)0.0098 (15)0.0103 (14)0.0011 (14)
Geometric parameters (Å, º) top
O5—C91.292 (4)N1—H2020.99 (6)
O5—H1050.92 (7)C1—C21.386 (4)
O4—C81.241 (4)C1—C61.394 (5)
O7—C101.302 (4)C1—C71.505 (4)
O7—H1070.95 (5)C2—C31.385 (4)
O1—C71.221 (4)C2—C81.513 (4)
O6—C91.201 (4)C3—C41.378 (4)
O3—C81.254 (4)C3—H1030.97 (5)
O3—H1011.40 (5)C4—C51.379 (4)
O2—C71.279 (4)C4—C91.484 (4)
O2—H1011.03 (5)C5—C61.383 (4)
O8—C101.215 (4)C5—C101.499 (4)
O9—H3010.92 (6)C6—H1060.95 (4)
O9—H3020.73 (8)C11—C11i1.501 (7)
N1—C111.484 (5)C11—H2050.97 (5)
N1—H2011.04 (6)C11—H2040.97 (5)
N1—H2030.99 (6)
C9—O5—H105105 (4)C4—C5—C10124.1 (3)
C10—O7—H107113 (3)C6—C5—C10117.1 (3)
C8—O3—H101108 (2)C5—C6—C1122.1 (3)
C7—O2—H101112 (3)C5—C6—H106120 (2)
H301—O9—H302113 (7)C1—C6—H106118 (2)
C11—N1—H201111 (3)O1—C7—O2120.8 (3)
C11—N1—H203110 (4)O1—C7—C1118.2 (3)
H201—N1—H203107 (5)O2—C7—C1121.0 (3)
C11—N1—H202117 (3)O4—C8—O3123.8 (3)
H201—N1—H20297 (4)O4—C8—C2116.8 (3)
H203—N1—H202114 (5)O3—C8—C2119.4 (3)
C2—C1—C6118.7 (3)O6—C9—O5124.7 (3)
C2—C1—C7126.6 (3)O6—C9—C4121.9 (3)
C6—C1—C7114.6 (3)O5—C9—C4113.3 (3)
C3—C2—C1118.6 (3)O8—C10—O7125.7 (3)
C3—C2—C8114.7 (3)O8—C10—C5120.7 (3)
C1—C2—C8126.7 (3)O7—C10—C5113.5 (3)
C4—C3—C2122.4 (3)N1—C11—C11i109.7 (4)
C4—C3—H103122 (3)N1—C11—H205110 (3)
C2—C3—H103116 (3)C11i—C11—H205107 (3)
C3—C4—C5119.3 (3)N1—C11—H204111 (3)
C3—C4—C9121.1 (3)C11i—C11—H204112 (3)
C5—C4—C9119.6 (3)H205—C11—H204107 (4)
C4—C5—C6118.7 (3)
Symmetry code: (i) x+2, y1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H301···O4ii0.92 (6)1.94 (6)2.837 (5)164 (5)
O2—H101···O31.03 (5)1.40 (5)2.427 (4)171 (5)
O7—H107···O4iii0.95 (5)1.62 (5)2.554 (3)169 (4)
O5—H105···O1iv0.92 (7)1.71 (7)2.610 (3)165 (7)
N1—H201···O6v1.04 (6)1.74 (6)2.759 (4)166 (5)
N1—H203···O8vi0.99 (6)1.87 (6)2.831 (4)165 (5)
N1—H202···O90.99 (6)1.80 (6)2.743 (5)156 (5)
O9—H302···O30.73 (8)2.20 (8)2.825 (4)145 (9)
Symmetry codes: (ii) x+1, y, z+1; (iii) x, y, z1; (iv) x1, y+1, z; (v) x+1, y1, z+1; (vi) x+2, y, z.
 

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