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In the title compound, 2C4H7N5O+·C10H6O82-, the benzene-1,2,4,5-tetracarboxylate anion lies on a centre of inversion, the two carboxyl H atoms being transferred to the endocyclic imine N atoms of two creatinine mol­ecules. Hydrogen bonds link the ions into a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700325X/bi2143sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680700325X/bi2143Isup2.hkl
Contains datablock I

CCDC reference: 636153

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.113
  • Data-to-parameter ratio = 16.1

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.10 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C18 H20 N6 O10 Atom count from _chemical_formula_moiety:C18 H20 N10 O10 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-RED (Stoe & Cie, 2005); data reduction: X-RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(creatininium) 2,5-dicarboxybenzene-1,4-dicarboxylate top
Crystal data top
2C4H7N5O+·C10H6O82F(000) = 500
Mr = 480.40Dx = 1.545 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2000 reflections
a = 7.4863 (16) Åθ = 2.5–29.2°
b = 12.825 (2) ŵ = 0.13 mm1
c = 10.846 (2) ÅT = 293 K
β = 97.418 (16)°Prism, colourless
V = 1032.6 (3) Å30.40 × 0.13 × 0.13 mm
Z = 2
Data collection top
Stoe IPDS II
diffractometer
2757 independent reflections
Radiation source: fine-focus sealed tube2450 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ scansθmax = 29.2°, θmin = 2.5°
Absorption correction: numerical
(X-SHAPE; Stoe & Cie, 2005)
h = 109
Tmin = 0.980, Tmax = 0.985k = 1717
8191 measured reflectionsl = 1414
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: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0512P)2 + 0.3677P]
where P = (Fo2 + 2Fc2)/3
2757 reflections(Δ/σ)max < 0.001
171 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.19 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
O10.0399 (2)0.22649 (10)0.47963 (11)0.0532 (4)
O20.34215 (17)0.56627 (8)0.67045 (9)0.0372 (3)
O30.22927 (16)0.41431 (8)0.71747 (9)0.0379 (3)
O40.60716 (16)0.32205 (8)0.75875 (9)0.0358 (3)
O50.49120 (16)0.22661 (7)0.90057 (10)0.0346 (2)
H50.534 (3)0.1774 (19)0.859 (2)0.062 (7)*
N10.10783 (16)0.40576 (9)0.27163 (10)0.0287 (2)
N20.25176 (19)0.53194 (11)0.40861 (12)0.0359 (3)
H2A0.280 (3)0.5476 (15)0.4876 (19)0.041 (5)*
H2B0.291 (3)0.5711 (18)0.351 (2)0.055 (6)*
N30.11704 (16)0.38080 (10)0.47436 (10)0.0297 (3)
H30.150 (3)0.3939 (16)0.559 (2)0.050 (5)*
C10.1125 (2)0.45905 (14)0.15395 (12)0.0392 (4)
H1A0.13590.53190.16900.059*
H1B0.00140.45080.10300.059*
H1C0.20610.42970.11210.059*
C20.16423 (17)0.44445 (10)0.38347 (11)0.0258 (3)
C30.0243 (2)0.29505 (11)0.42303 (13)0.0324 (3)
C40.0203 (2)0.30524 (11)0.28379 (12)0.0307 (3)
H4A0.08670.24920.25050.037*
H4B0.10230.30560.24200.037*
C50.32556 (17)0.49221 (9)0.74337 (10)0.0221 (2)
C60.42237 (16)0.49782 (9)0.87503 (10)0.0207 (2)
C70.50587 (16)0.40898 (9)0.93080 (11)0.0206 (2)
C80.53721 (17)0.31532 (9)0.85335 (11)0.0224 (2)
C90.58125 (17)0.41081 (9)1.05555 (11)0.0224 (2)
H9A0.63400.35091.09240.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0771 (9)0.0419 (7)0.0380 (6)0.0200 (6)0.0024 (6)0.0118 (5)
O20.0637 (7)0.0239 (5)0.0216 (4)0.0117 (5)0.0041 (4)0.0038 (4)
O30.0532 (6)0.0333 (5)0.0237 (4)0.0197 (5)0.0083 (4)0.0038 (4)
O40.0571 (7)0.0259 (5)0.0270 (5)0.0014 (4)0.0149 (4)0.0030 (4)
O50.0553 (7)0.0161 (4)0.0351 (5)0.0008 (4)0.0156 (5)0.0022 (4)
N10.0373 (6)0.0288 (6)0.0192 (5)0.0030 (4)0.0011 (4)0.0024 (4)
N20.0458 (7)0.0382 (7)0.0238 (5)0.0141 (6)0.0051 (5)0.0041 (5)
N30.0371 (6)0.0318 (6)0.0193 (5)0.0032 (5)0.0000 (4)0.0006 (4)
C10.0509 (9)0.0471 (9)0.0198 (6)0.0135 (7)0.0049 (6)0.0014 (6)
C20.0273 (6)0.0291 (6)0.0207 (5)0.0011 (5)0.0026 (4)0.0016 (5)
C30.0403 (7)0.0285 (6)0.0270 (6)0.0001 (5)0.0014 (5)0.0026 (5)
C40.0390 (7)0.0265 (6)0.0256 (6)0.0012 (5)0.0001 (5)0.0027 (5)
C50.0284 (6)0.0191 (5)0.0179 (5)0.0010 (4)0.0003 (4)0.0011 (4)
C60.0260 (5)0.0176 (5)0.0179 (5)0.0007 (4)0.0000 (4)0.0001 (4)
C70.0264 (5)0.0154 (5)0.0194 (5)0.0004 (4)0.0010 (4)0.0022 (4)
C80.0286 (6)0.0171 (5)0.0208 (5)0.0013 (4)0.0002 (4)0.0023 (4)
C90.0290 (6)0.0167 (5)0.0202 (5)0.0026 (4)0.0016 (4)0.0003 (4)
Geometric parameters (Å, º) top
O1—C31.2070 (19)N3—H30.93 (2)
O2—C51.2524 (15)C1—H1A0.960
O3—C51.2427 (15)C1—H1B0.960
O4—C81.2137 (16)C1—H1C0.960
O5—C81.3118 (15)C3—C41.5123 (19)
O5—H50.86 (2)C4—H4A0.970
N1—C21.3279 (16)C4—H4B0.970
N1—C11.4522 (17)C5—C61.5174 (16)
N1—C41.4599 (18)C6—C9i1.3950 (16)
N2—C21.3102 (18)C6—C71.3990 (16)
N2—H2A0.88 (2)C7—C91.3973 (16)
N2—H2B0.89 (2)C7—C81.5015 (16)
N3—C21.3612 (17)C9—C6i1.3950 (15)
N3—C31.3790 (18)C9—H9A0.930
C8—O5—H5107.4 (16)N1—C4—C3102.43 (11)
C2—N1—C1125.88 (12)N1—C4—H4A111.3
C2—N1—C4109.93 (11)C3—C4—H4A111.3
C1—N1—C4123.85 (11)N1—C4—H4B111.3
C2—N2—H2A116.6 (13)C3—C4—H4B111.3
C2—N2—H2B122.8 (15)H4A—C4—H4B109.2
H2A—N2—H2B120.4 (19)O3—C5—O2124.67 (11)
C2—N3—C3110.49 (11)O3—C5—C6116.33 (10)
C2—N3—H3122.8 (13)O2—C5—C6118.95 (11)
C3—N3—H3126.6 (13)C9i—C6—C7119.31 (10)
N1—C1—H1A109.5C9i—C6—C5120.50 (10)
N1—C1—H1B109.5C7—C6—C5120.05 (10)
H1A—C1—H1B109.5C9—C7—C6120.47 (10)
N1—C1—H1C109.5C9—C7—C8118.84 (10)
H1A—C1—H1C109.5C6—C7—C8120.20 (10)
H1B—C1—H1C109.5O4—C8—O5123.74 (11)
N2—C2—N1126.98 (13)O4—C8—C7122.11 (11)
N2—C2—N3122.17 (12)O5—C8—C7114.05 (10)
N1—C2—N3110.84 (12)C6i—C9—C7120.21 (10)
O1—C3—N3126.04 (13)C6i—C9—H9A119.9
O1—C3—C4127.81 (14)C7—C9—H9A119.9
N3—C3—C4106.15 (12)
C1—N1—C2—N28.1 (2)O2—C5—C6—C9i45.17 (17)
C4—N1—C2—N2178.41 (14)O3—C5—C6—C743.22 (17)
C1—N1—C2—N3171.13 (14)O2—C5—C6—C7139.17 (13)
C4—N1—C2—N32.38 (16)C9i—C6—C7—C91.5 (2)
C3—N3—C2—N2179.15 (14)C5—C6—C7—C9174.22 (11)
C3—N3—C2—N10.10 (16)C9i—C6—C7—C8170.39 (11)
C2—N3—C3—O1177.56 (16)C5—C6—C7—C813.91 (17)
C2—N3—C3—C42.40 (16)C9—C7—C8—O4122.31 (14)
C2—N1—C4—C33.60 (15)C6—C7—C8—O449.70 (18)
C1—N1—C4—C3170.06 (14)C9—C7—C8—O554.33 (16)
O1—C3—C4—N1176.42 (17)C6—C7—C8—O5133.67 (13)
N3—C3—C4—N13.54 (15)C6—C7—C9—C6i1.5 (2)
O3—C5—C6—C9i132.44 (13)C8—C7—C9—C6i170.48 (11)
Symmetry code: (i) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O30.93 (2)1.76 (2)2.6965 (15)176 (2)
N2—H2A···O20.88 (2)1.99 (2)2.8672 (17)173.7 (18)
N2—H2B···O4ii0.89 (2)2.02 (2)2.9004 (17)170 (2)
O5—H5···O2iii0.86 (2)1.75 (3)2.5743 (15)159 (2)
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x+1, y1/2, z+3/2.
 

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