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In the crystal structure of the title compound, C5H6N+·C6H3N2O4, the 5-carboxy­pyrazine-2-carboxyl­ate (pdc) mono­anion lies entirely on a mirror plane. The N and C atoms of the cation, together with their attached H atoms, lie on the same mirror plane. A supra­molecular network is assembled between the pdc anions and pyridinium cations via N—H...O, O—H...O and C—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603039X/xu2105sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603039X/xu2105Isup2.hkl
Contains datablock I

CCDC reference: 625008

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.036
  • wR factor = 0.109
  • Data-to-parameter ratio = 11.0

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.15
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Pyridinium 5-carboxypyrazine-2-carboxylate top
Crystal data top
C5H6N+·C6H3N2O4F(000) = 256
Mr = 247.21Dx = 1.535 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybCell parameters from 1432 reflections
a = 9.237 (2) Åθ = 2.3–26.4°
b = 6.7553 (18) ŵ = 0.12 mm1
c = 9.529 (3) ÅT = 294 K
β = 115.905 (4)°Block, colourless
V = 534.9 (2) Å30.28 × 0.24 × 0.20 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
943 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 26.4°, θmin = 2.4°
φ and ω scansh = 119
3034 measured reflectionsk = 88
1195 independent reflectionsl = 711
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.0544P)2 + 0.1076P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
1195 reflectionsΔρmax = 0.22 e Å3
109 parametersΔρmin = 0.17 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.046 (8)
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
O10.72292 (16)0.25000.55050 (16)0.0473 (4)
O20.46005 (16)0.25000.39199 (15)0.0474 (4)
H20.491 (3)0.25000.319 (2)0.057*
O30.25524 (17)0.25000.99500 (16)0.0470 (4)
O40.51718 (17)0.25001.15898 (15)0.0468 (4)
N10.65329 (17)0.25000.80481 (17)0.0341 (4)
N20.32829 (17)0.25000.74574 (17)0.0346 (4)
C10.5840 (2)0.25000.5279 (2)0.0306 (4)
C20.5351 (2)0.25000.65984 (19)0.0272 (4)
C30.3748 (2)0.25000.6315 (2)0.0351 (5)
H30.29640.25000.52870.042*
C40.4456 (2)0.25000.89071 (19)0.0270 (4)
C50.6061 (2)0.25000.9187 (2)0.0343 (5)
H50.68440.25001.02160.041*
C60.4004 (2)0.25001.0260 (2)0.0304 (4)
C70.06181 (18)0.0778 (2)0.21219 (16)0.0442 (4)
H70.09580.04010.18580.053*
C80.03312 (18)0.0743 (3)0.28930 (17)0.0491 (4)
H80.06470.04560.31520.059*
C90.0810 (2)0.25000.3278 (2)0.0484 (6)
H90.14590.25000.37990.058*
N30.10531 (19)0.25000.17522 (19)0.0386 (4)
H3A0.170 (3)0.25000.121 (3)0.066 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0314 (7)0.0846 (11)0.0344 (8)0.0000.0222 (6)0.000
O20.0328 (7)0.0928 (12)0.0218 (7)0.0000.0168 (6)0.000
O30.0401 (8)0.0753 (11)0.0385 (8)0.0000.0294 (7)0.000
O40.0436 (8)0.0792 (11)0.0247 (7)0.0000.0216 (6)0.000
N10.0267 (8)0.0559 (10)0.0239 (7)0.0000.0149 (6)0.000
N20.0281 (8)0.0541 (10)0.0275 (8)0.0000.0177 (7)0.000
C10.0322 (9)0.0394 (10)0.0264 (9)0.0000.0184 (7)0.000
C20.0284 (9)0.0351 (10)0.0227 (9)0.0000.0155 (7)0.000
C30.0275 (9)0.0584 (12)0.0216 (9)0.0000.0126 (7)0.000
C40.0323 (9)0.0305 (9)0.0245 (9)0.0000.0184 (7)0.000
C50.0310 (9)0.0531 (12)0.0209 (8)0.0000.0133 (7)0.000
C60.0390 (10)0.0338 (10)0.0279 (9)0.0000.0235 (8)0.000
C70.0456 (8)0.0465 (9)0.0417 (8)0.0057 (7)0.0201 (7)0.0025 (7)
C80.0471 (8)0.0577 (10)0.0443 (8)0.0127 (7)0.0215 (7)0.0067 (7)
C90.0290 (10)0.0869 (18)0.0363 (11)0.0000.0207 (9)0.000
N30.0298 (8)0.0595 (12)0.0324 (9)0.0000.0192 (7)0.000
Geometric parameters (Å, º) top
O1—C11.205 (2)C4—C51.387 (2)
O2—C11.301 (2)C4—C61.518 (2)
O2—H20.863 (10)C5—H50.9300
O3—C61.241 (2)C7—N31.3276 (17)
O4—C61.255 (2)C7—C81.368 (2)
N1—C21.335 (2)C7—H70.9300
N1—C51.335 (2)C8—C91.3714 (19)
N2—C41.332 (2)C8—H80.9300
N2—C31.333 (2)C9—C8i1.371 (2)
C1—C21.510 (2)C9—H90.9300
C2—C31.384 (2)N3—C7i1.3276 (17)
C3—H30.9300N3—H3A0.94 (3)
C1—O2—H2110.1 (16)C4—C5—H5118.5
C2—N1—C5115.55 (15)O3—C6—O4127.06 (16)
C4—N2—C3116.13 (15)O3—C6—C4117.88 (16)
O1—C1—O2125.68 (16)O4—C6—C4115.06 (15)
O1—C1—C2122.30 (16)N3—C7—C8119.80 (14)
O2—C1—C2112.03 (15)N3—C7—H7120.1
N1—C2—C3121.55 (15)C8—C7—H7120.1
N1—C2—C1117.02 (15)C7—C8—C9119.06 (15)
C3—C2—C1121.43 (15)C7—C8—H8120.5
N2—C3—C2122.65 (16)C9—C8—H8120.5
N2—C3—H3118.7C8i—C9—C8119.88 (18)
C2—C3—H3118.7C8i—C9—H9120.1
N2—C4—C5121.11 (15)C8—C9—H9120.1
N2—C4—C6118.65 (15)C7—N3—C7i122.38 (17)
C5—C4—C6120.24 (16)C7—N3—H3A118.81 (9)
N1—C5—C4123.02 (17)C7i—N3—H3A118.81 (9)
N1—C5—H5118.5
C5—N1—C2—C30.0C2—N1—C5—C40.000 (1)
C5—N1—C2—C1180.0N2—C4—C5—N10.000 (1)
O1—C1—C2—N10.0C6—C4—C5—N1180.0
O2—C1—C2—N1180.0N2—C4—C6—O30.000 (1)
O1—C1—C2—C3180.0C5—C4—C6—O3180.0
O2—C1—C2—C30.0N2—C4—C6—O4180.0
C4—N2—C3—C20.0C5—C4—C6—O40.000 (1)
N1—C2—C3—N20.0N3—C7—C8—C90.3 (2)
C1—C2—C3—N2180.0C7—C8—C9—C8i0.2 (3)
C3—N2—C4—C50.000 (1)C8—C7—N3—C7i0.9 (3)
C3—N2—C4—C6180.0
Symmetry code: (i) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O4ii0.86 (1)1.64 (1)2.4964 (19)170 (2)
N3—H3A···O3ii0.94 (3)1.70 (3)2.635 (2)170 (2)
C9—H9···O1iii0.932.423.338 (2)171
Symmetry codes: (ii) x, y, z1; (iii) x1, y, z.
 

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