Ethyl­enediammonium bis­(trihydrogen 1,2,4,5-benzene­tetra­carboxyl­ate) dihydrate

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.

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

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Computing details

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

Crystal data

C2H10N2^2+·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) Å^3	0.35 × 0.35 × 0.32 mm

Data collection

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

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)] = 0.055	Hydrogen site location: difference Fourier map
wR(F^2) = 0.200	All H-atom parameters refined
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0722P)^2 + 2.3708P] where P = (Fo^2 + 2Fc^2)/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

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
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C11^i	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—C11^i	109.7 (4)
C4—C3—H103	122 (3)	N1—C11—H205	110 (3)
C2—C3—H103	116 (3)	C11^i—C11—H205	107 (3)
C3—C4—C5	119.3 (3)	N1—C11—H204	111 (3)
C3—C4—C9	121.1 (3)	C11^i—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)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H301···O4^ii	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···O4^iii	0.95 (5)	1.62 (5)	2.554 (3)	169 (4)
O5—H105···O1^iv	0.92 (7)	1.71 (7)	2.610 (3)	165 (7)
N1—H201···O6^v	1.04 (6)	1.74 (6)	2.759 (4)	166 (5)
N1—H203···O8^vi	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.