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The title compound, C5H8N3+·C4H3O4, contains edge-fused [R21(6)R22(8)R22(8)R65(26)R21(6)] motifs involving 2,6-diamino­pyridinium and hydrogen fumarate ions. In these motifs, 2,6-diamino­pyridinium and hydrogen fumarate ions are connected by N—H...N, N—H...O and O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031096/at2081sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031096/at2081Isup2.hkl
Contains datablock I

CCDC reference: 620536

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.028
  • wR factor = 0.070
  • Data-to-parameter ratio = 6.3

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.33 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.31
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.99 From the CIF: _reflns_number_total 1045 Count of symmetry unique reflns 1045 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); 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).

2,6-diaminopyridinium hydrogen fumarate top
Crystal data top
C5H8N3+·C4H3O4F(000) = 236
Mr = 225.21Dx = 1.479 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 10903 reflections
a = 3.7834 (3) Åθ = 2.0–27.9°
b = 13.3967 (13) ŵ = 0.12 mm1
c = 10.0703 (8) ÅT = 296 K
β = 97.635 (6)°Prism, colourless
V = 505.89 (8) Å30.60 × 0.29 × 0.06 mm
Z = 2
Data collection top
Stoe IPDS-2
diffractometer
1045 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus951 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.039
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.0°
ω scansh = 44
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1616
Tmin = 0.960, Tmax = 0.993l = 1212
5811 measured reflections
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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0376P)2 + 0.0356P]
where P = (Fo2 + 2Fc2)/3
1045 reflections(Δ/σ)max < 0.001
165 parametersΔρmax = 0.09 e Å3
1 restraintΔρmin = 0.15 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
C10.7773 (6)0.26322 (16)0.3689 (2)0.0378 (5)
C20.8996 (7)0.29741 (18)0.2544 (2)0.0447 (6)
H20.90420.25590.18070.054*
C31.0149 (7)0.39481 (19)0.2521 (2)0.0467 (5)
H31.09710.41870.17510.056*
C41.0129 (7)0.45786 (18)0.3597 (2)0.0456 (5)
H41.09160.52340.35570.055*
C50.8898 (6)0.42125 (16)0.4752 (2)0.0403 (5)
C60.4436 (6)0.05435 (17)1.0306 (2)0.0422 (5)
C70.4850 (7)0.11145 (18)0.9075 (2)0.0449 (5)
H70.54850.07620.83470.054*
C80.4387 (7)0.20751 (18)0.8938 (2)0.0443 (5)
H80.35850.24330.96310.053*
C90.5098 (7)0.26191 (17)0.7709 (2)0.0442 (5)
N10.7820 (5)0.32483 (14)0.47516 (19)0.0374 (4)
N20.6634 (6)0.16754 (14)0.3857 (2)0.0460 (5)
N30.8620 (7)0.47546 (17)0.5846 (2)0.0521 (5)
O10.5335 (6)0.03915 (13)1.02012 (18)0.0606 (5)
H1A0.50790.06871.08950.091*
O20.3360 (6)0.09026 (13)1.12802 (15)0.0539 (5)
O30.5382 (6)0.21378 (15)0.66804 (18)0.0620 (5)
O40.5474 (7)0.35467 (14)0.77834 (19)0.0676 (6)
H10.732 (8)0.298 (2)0.549 (3)0.057 (8)*
H2A0.567 (8)0.137 (2)0.308 (3)0.055 (8)*
H2B0.556 (9)0.155 (3)0.452 (3)0.067 (10)*
H3A0.984 (9)0.529 (3)0.596 (3)0.064 (9)*
H3B0.786 (9)0.445 (3)0.659 (4)0.075 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0399 (11)0.0361 (11)0.0373 (12)0.0053 (9)0.0046 (9)0.0022 (9)
C20.0516 (13)0.0470 (13)0.0367 (11)0.0051 (11)0.0106 (9)0.0008 (10)
C30.0477 (13)0.0529 (14)0.0409 (12)0.0006 (11)0.0110 (10)0.0107 (11)
C40.0479 (13)0.0382 (12)0.0519 (13)0.0023 (10)0.0109 (10)0.0098 (10)
C50.0401 (12)0.0355 (12)0.0454 (12)0.0024 (9)0.0059 (9)0.0042 (9)
C60.0518 (14)0.0390 (12)0.0368 (12)0.0050 (10)0.0097 (9)0.0050 (9)
C70.0549 (14)0.0441 (13)0.0379 (11)0.0026 (11)0.0142 (9)0.0043 (10)
C80.0556 (14)0.0431 (13)0.0369 (12)0.0012 (11)0.0164 (10)0.0031 (10)
C90.0518 (13)0.0433 (14)0.0393 (12)0.0007 (11)0.0133 (10)0.0003 (10)
N10.0442 (10)0.0346 (9)0.0342 (9)0.0017 (8)0.0085 (7)0.0035 (7)
N20.0616 (14)0.0370 (10)0.0403 (11)0.0035 (9)0.0099 (10)0.0001 (9)
N30.0692 (15)0.0390 (12)0.0502 (12)0.0087 (11)0.0155 (10)0.0054 (9)
O10.0998 (15)0.0413 (10)0.0456 (10)0.0030 (9)0.0276 (10)0.0009 (7)
O20.0781 (12)0.0485 (10)0.0385 (9)0.0014 (9)0.0203 (8)0.0059 (7)
O30.1008 (16)0.0505 (10)0.0398 (9)0.0062 (10)0.0275 (9)0.0034 (8)
O40.1154 (18)0.0422 (10)0.0522 (11)0.0008 (10)0.0365 (11)0.0011 (8)
Geometric parameters (Å, º) top
C1—N11.350 (3)C6—C71.482 (3)
C1—N21.370 (3)C7—C81.304 (3)
C1—C21.376 (3)C7—H70.9300
C2—C31.377 (4)C8—C91.491 (3)
C2—H20.9300C8—H80.9300
C3—C41.374 (4)C9—O31.237 (3)
C3—H30.9300C9—O41.252 (3)
C4—C51.398 (3)N1—H10.87 (3)
C4—H40.9300N2—H2A0.92 (3)
C5—N31.336 (3)N2—H2B0.84 (4)
C5—N11.354 (3)N3—H3A0.86 (4)
C6—O21.211 (3)N3—H3B0.93 (4)
C6—O11.306 (3)O1—H1A0.8200
N1—C1—N2116.5 (2)C8—C7—H7117.6
N1—C1—C2119.3 (2)C6—C7—H7117.6
N2—C1—C2124.1 (2)C7—C8—C9122.3 (2)
C3—C2—C1118.2 (2)C7—C8—H8118.9
C3—C2—H2120.9C9—C8—H8118.9
C1—C2—H2120.9O3—C9—O4123.1 (2)
C4—C3—C2122.3 (2)O3—C9—C8119.1 (2)
C4—C3—H3118.9O4—C9—C8117.9 (2)
C2—C3—H3118.9C1—N1—C5123.75 (18)
C3—C4—C5118.5 (2)C1—N1—H1117 (2)
C3—C4—H4120.7C5—N1—H1119 (2)
C5—C4—H4120.7C1—N2—H2A114.3 (18)
N3—C5—N1117.5 (2)C1—N2—H2B119 (2)
N3—C5—C4124.6 (2)H2A—N2—H2B114 (3)
N1—C5—C4117.9 (2)C5—N3—H3A118 (2)
O2—C6—O1124.4 (2)C5—N3—H3B119 (2)
O2—C6—C7123.8 (2)H3A—N3—H3B119 (3)
O1—C6—C7111.72 (19)C6—O1—H1A109.5
C8—C7—C6124.8 (2)
N1—C1—C2—C31.5 (3)C6—C7—C8—C9175.5 (2)
N2—C1—C2—C3178.3 (2)C7—C8—C9—O316.0 (4)
C1—C2—C3—C40.3 (4)C7—C8—C9—O4162.2 (3)
C2—C3—C4—C50.1 (4)N2—C1—N1—C5179.5 (2)
C3—C4—C5—N3177.5 (3)C2—C1—N1—C52.4 (3)
C3—C4—C5—N10.6 (3)N3—C5—N1—C1176.3 (2)
O2—C6—C7—C85.8 (4)C4—C5—N1—C12.0 (3)
O1—C6—C7—C8174.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O4i0.821.722.530 (2)172
N1—H1···O30.87 (3)1.87 (3)2.704 (3)161 (3)
N2—H2A···O2ii0.92 (3)2.00 (3)2.913 (3)171 (3)
N2—H2B···O30.84 (4)2.32 (3)3.009 (3)138 (3)
N3—H3A···N2iii0.86 (4)2.28 (4)3.129 (3)175 (3)
N3—H3B···O40.93 (4)2.00 (4)2.908 (3)164 (3)
Symmetry codes: (i) x+1, y1/2, z+2; (ii) x, y, z1; (iii) x+2, y+1/2, z+1.
 

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