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
CCDC reference: 298485
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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−·2H2O | Z = 1 |
Mr = 604.44 | F(000) = 314 |
Triclinic, P1 | Dx = 1.687 Mg m−3 |
a = 8.118 (2) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 8.2266 (17) Å | Cell parameters from 2246 reflections |
c = 9.596 (3) Å | θ = 2.6–27.4° |
α = 83.50 (1)° | µ = 0.15 mm−1 |
β = 77.178 (13)° | T = 293 K |
γ = 72.395 (10)° | Block, colourless |
V = 594.9 (2) Å3 | 0.35 × 0.35 × 0.32 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2074 reflections with I > 2σ(I) |
Radiation source: rotor target | Rint = 0.033 |
Graphite monochromator | θmax = 27.5°, θmin = 2.6° |
Oscillation scans | h = −10→9 |
4366 measured reflections | k = −10→10 |
2484 independent reflections | l = −12→12 |
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)] = 0.055 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.200 | All 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 parameters | Δρmax = 0.61 e Å−3 |
1 restraint | Δρmin = −0.60 e Å−3 |
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 | Uiso*/Ueq | |
O5 | 0.1685 (3) | 0.5467 (3) | 0.0613 (3) | 0.0324 (6) | |
O4 | 0.4565 (3) | 0.2125 (4) | 0.4121 (2) | 0.0297 (6) | |
O7 | 0.4551 (4) | 0.1883 (3) | −0.3199 (3) | 0.0297 (6) | |
O1 | 0.9117 (3) | −0.1961 (3) | −0.0030 (3) | 0.0328 (6) | |
O6 | 0.2586 (4) | 0.5046 (3) | −0.1700 (3) | 0.0332 (6) | |
O3 | 0.7459 (3) | 0.1156 (4) | 0.3598 (3) | 0.0311 (6) | |
O2 | 0.9242 (3) | −0.1065 (4) | 0.1980 (3) | 0.0328 (6) | |
O8 | 0.6372 (4) | 0.3513 (4) | −0.3435 (3) | 0.0358 (7) | |
O9 | 0.8316 (4) | −0.0926 (4) | 0.6035 (4) | 0.0408 (7) | |
N1 | 1.1091 (4) | −0.3843 (4) | 0.5920 (3) | 0.0281 (7) | |
H301 | 0.734 (7) | −0.131 (7) | 0.617 (6) | 0.046 (14)* | |
H205 | 1.124 (6) | −0.629 (6) | 0.559 (5) | 0.036 (12)* | |
H106 | 0.760 (5) | 0.022 (5) | −0.146 (4) | 0.025 (10)* | |
H101 | 0.859 (7) | −0.010 (7) | 0.267 (6) | 0.048 (14)* | |
H103 | 0.372 (6) | 0.370 (6) | 0.206 (5) | 0.032 (11)* | |
H204 | 0.942 (7) | −0.533 (7) | 0.650 (6) | 0.048 (14)* | |
H107 | 0.470 (6) | 0.199 (6) | −0.421 (5) | 0.035 (12)* | |
H105 | 0.084 (9) | 0.630 (9) | 0.024 (7) | 0.09 (2)* | |
H201 | 1.154 (8) | −0.408 (7) | 0.688 (6) | 0.061 (16)* | |
H203 | 1.213 (8) | −0.384 (7) | 0.516 (6) | 0.062 (16)* | |
H202 | 1.026 (8) | −0.269 (8) | 0.612 (6) | 0.059 (16)* | |
H302 | 0.824 (11) | −0.014 (11) | 0.558 (9) | 0.10 (3)* | |
C1 | 0.7031 (4) | 0.0632 (4) | 0.0656 (3) | 0.0199 (6) | |
C2 | 0.5862 (4) | 0.1676 (4) | 0.1699 (3) | 0.0184 (6) | |
C3 | 0.4467 (4) | 0.2961 (4) | 0.1306 (3) | 0.0201 (6) | |
C4 | 0.4245 (4) | 0.3285 (4) | −0.0091 (3) | 0.0192 (6) | |
C5 | 0.5456 (4) | 0.2309 (4) | −0.1147 (3) | 0.0178 (6) | |
C6 | 0.6800 (4) | 0.0963 (4) | −0.0756 (3) | 0.0205 (6) | |
C7 | 0.8542 (4) | −0.0901 (4) | 0.0883 (4) | 0.0220 (7) | |
C8 | 0.5976 (4) | 0.1621 (4) | 0.3257 (3) | 0.0219 (7) | |
C9 | 0.2745 (4) | 0.4685 (4) | −0.0479 (3) | 0.0207 (6) | |
C10 | 0.5470 (4) | 0.2663 (4) | −0.2716 (3) | 0.0213 (6) | |
C11 | 1.0330 (5) | −0.5197 (5) | 0.5689 (4) | 0.0272 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O5 | 0.0288 (13) | 0.0301 (13) | 0.0250 (13) | 0.0122 (11) | −0.0049 (10) | −0.0056 (10) |
O4 | 0.0308 (13) | 0.0430 (15) | 0.0141 (11) | −0.0052 (11) | −0.0079 (9) | −0.0042 (10) |
O7 | 0.0372 (14) | 0.0373 (14) | 0.0179 (12) | −0.0148 (11) | −0.0076 (10) | 0.0008 (10) |
O1 | 0.0281 (13) | 0.0266 (13) | 0.0356 (15) | 0.0064 (10) | −0.0077 (11) | −0.0061 (11) |
O6 | 0.0342 (14) | 0.0337 (14) | 0.0229 (13) | 0.0053 (11) | −0.0109 (10) | 0.0029 (10) |
O3 | 0.0280 (13) | 0.0405 (15) | 0.0252 (13) | −0.0046 (11) | −0.0131 (10) | −0.0019 (11) |
O2 | 0.0256 (12) | 0.0359 (14) | 0.0319 (14) | 0.0040 (11) | −0.0140 (10) | −0.0002 (11) |
O8 | 0.0438 (16) | 0.0467 (17) | 0.0208 (13) | −0.0230 (13) | −0.0037 (11) | 0.0047 (11) |
O9 | 0.0371 (16) | 0.0384 (17) | 0.0411 (17) | −0.0023 (13) | −0.0096 (13) | 0.0021 (14) |
N1 | 0.0307 (15) | 0.0366 (17) | 0.0221 (15) | −0.0135 (14) | −0.0113 (12) | 0.0005 (13) |
C1 | 0.0161 (13) | 0.0204 (15) | 0.0218 (15) | −0.0042 (11) | −0.0029 (11) | −0.0004 (12) |
C2 | 0.0196 (14) | 0.0194 (14) | 0.0157 (14) | −0.0046 (11) | −0.0053 (11) | 0.0017 (11) |
C3 | 0.0204 (14) | 0.0188 (14) | 0.0186 (15) | −0.0026 (12) | −0.0018 (11) | −0.0023 (12) |
C4 | 0.0197 (14) | 0.0184 (14) | 0.0177 (15) | −0.0032 (11) | −0.0021 (11) | −0.0022 (11) |
C5 | 0.0205 (14) | 0.0189 (14) | 0.0152 (14) | −0.0060 (11) | −0.0039 (11) | −0.0038 (11) |
C6 | 0.0195 (14) | 0.0182 (14) | 0.0200 (15) | −0.0017 (12) | −0.0009 (12) | −0.0021 (12) |
C7 | 0.0173 (14) | 0.0231 (16) | 0.0237 (16) | −0.0034 (12) | −0.0053 (12) | 0.0021 (12) |
C8 | 0.0289 (16) | 0.0221 (15) | 0.0156 (14) | −0.0068 (13) | −0.0072 (12) | −0.0007 (12) |
C9 | 0.0211 (14) | 0.0202 (15) | 0.0197 (15) | −0.0034 (12) | −0.0046 (12) | −0.0020 (12) |
C10 | 0.0220 (15) | 0.0195 (15) | 0.0175 (15) | 0.0000 (12) | −0.0016 (11) | −0.0020 (11) |
C11 | 0.0310 (18) | 0.0309 (18) | 0.0222 (18) | −0.0098 (15) | −0.0103 (14) | 0.0011 (14) |
Geometric parameters (Å, º) top
O5—C9 | 1.292 (4) | N1—H202 | 0.99 (6) |
O5—H105 | 0.92 (7) | C1—C2 | 1.386 (4) |
O4—C8 | 1.241 (4) | C1—C6 | 1.394 (5) |
O7—C10 | 1.302 (4) | C1—C7 | 1.505 (4) |
O7—H107 | 0.95 (5) | C2—C3 | 1.385 (4) |
O1—C7 | 1.221 (4) | C2—C8 | 1.513 (4) |
O6—C9 | 1.201 (4) | C3—C4 | 1.378 (4) |
O3—C8 | 1.254 (4) | C3—H103 | 0.97 (5) |
O3—H101 | 1.40 (5) | C4—C5 | 1.379 (4) |
O2—C7 | 1.279 (4) | C4—C9 | 1.484 (4) |
O2—H101 | 1.03 (5) | C5—C6 | 1.383 (4) |
O8—C10 | 1.215 (4) | C5—C10 | 1.499 (4) |
O9—H301 | 0.92 (6) | C6—H106 | 0.95 (4) |
O9—H302 | 0.73 (8) | C11—C11i | 1.501 (7) |
N1—C11 | 1.484 (5) | C11—H205 | 0.97 (5) |
N1—H201 | 1.04 (6) | C11—H204 | 0.97 (5) |
N1—H203 | 0.99 (6) | | |
| | | |
C9—O5—H105 | 105 (4) | C4—C5—C10 | 124.1 (3) |
C10—O7—H107 | 113 (3) | C6—C5—C10 | 117.1 (3) |
C8—O3—H101 | 108 (2) | C5—C6—C1 | 122.1 (3) |
C7—O2—H101 | 112 (3) | C5—C6—H106 | 120 (2) |
H301—O9—H302 | 113 (7) | C1—C6—H106 | 118 (2) |
C11—N1—H201 | 111 (3) | O1—C7—O2 | 120.8 (3) |
C11—N1—H203 | 110 (4) | O1—C7—C1 | 118.2 (3) |
H201—N1—H203 | 107 (5) | O2—C7—C1 | 121.0 (3) |
C11—N1—H202 | 117 (3) | O4—C8—O3 | 123.8 (3) |
H201—N1—H202 | 97 (4) | O4—C8—C2 | 116.8 (3) |
H203—N1—H202 | 114 (5) | O3—C8—C2 | 119.4 (3) |
C2—C1—C6 | 118.7 (3) | O6—C9—O5 | 124.7 (3) |
C2—C1—C7 | 126.6 (3) | O6—C9—C4 | 121.9 (3) |
C6—C1—C7 | 114.6 (3) | O5—C9—C4 | 113.3 (3) |
C3—C2—C1 | 118.6 (3) | O8—C10—O7 | 125.7 (3) |
C3—C2—C8 | 114.7 (3) | O8—C10—C5 | 120.7 (3) |
C1—C2—C8 | 126.7 (3) | O7—C10—C5 | 113.5 (3) |
C4—C3—C2 | 122.4 (3) | N1—C11—C11i | 109.7 (4) |
C4—C3—H103 | 122 (3) | N1—C11—H205 | 110 (3) |
C2—C3—H103 | 116 (3) | C11i—C11—H205 | 107 (3) |
C3—C4—C5 | 119.3 (3) | N1—C11—H204 | 111 (3) |
C3—C4—C9 | 121.1 (3) | C11i—C11—H204 | 112 (3) |
C5—C4—C9 | 119.6 (3) | H205—C11—H204 | 107 (4) |
C4—C5—C6 | 118.7 (3) | | |
Symmetry code: (i) −x+2, −y−1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H301···O4ii | 0.92 (6) | 1.94 (6) | 2.837 (5) | 164 (5) |
O2—H101···O3 | 1.03 (5) | 1.40 (5) | 2.427 (4) | 171 (5) |
O7—H107···O4iii | 0.95 (5) | 1.62 (5) | 2.554 (3) | 169 (4) |
O5—H105···O1iv | 0.92 (7) | 1.71 (7) | 2.610 (3) | 165 (7) |
N1—H201···O6v | 1.04 (6) | 1.74 (6) | 2.759 (4) | 166 (5) |
N1—H203···O8vi | 0.99 (6) | 1.87 (6) | 2.831 (4) | 165 (5) |
N1—H202···O9 | 0.99 (6) | 1.80 (6) | 2.743 (5) | 156 (5) |
O9—H302···O3 | 0.73 (8) | 2.20 (8) | 2.825 (4) | 145 (9) |
Symmetry codes: (ii) −x+1, −y, −z+1; (iii) x, y, z−1; (iv) x−1, y+1, z; (v) x+1, y−1, z+1; (vi) −x+2, −y, −z. |