Download citation
Download citation
link to html
In the title compound, 2C5H8N3+·C2O22−·2H2O, the 2,6-diamino­pyridinium ions are linked to centrosymmetric oxalate ions and water mol­ecules through N—H...O and O—H...O hydrogen bonds, generating edge-fused [R21(6)R12(5)R22(9)R42(8)R66(17)] motifs.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603755X/ob3017sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680603755X/ob3017Isup2.hkl
Contains datablock I

CCDC reference: 624955

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.089
  • Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level C 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 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C6 - C6_a ... 1.55 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 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 1 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, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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(2,6-diaminopyridinium) oxalate dihydrate top
Crystal data top
2C5H8N3+·C2O42·2H2OF(000) = 364
Mr = 344.34Dx = 1.444 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 14420 reflections
a = 8.0068 (6) Åθ = 2.6–27.9°
b = 15.4788 (8) ŵ = 0.12 mm1
c = 7.0250 (5) ÅT = 296 K
β = 114.531 (6)°Prism, light yellow
V = 792.06 (9) Å30.65 × 0.44 × 0.28 mm
Z = 2
Data collection top
Stoe IPDS-2
diffractometer
1551 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1401 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.047
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.6°
ω scansh = 99
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1818
Tmin = 0.936, Tmax = 0.971l = 88
11192 measured reflections
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)] = 0.032All H-atom parameters refined
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.0479P)2 + 0.1298P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1551 reflectionsΔρmax = 0.15 e Å3
150 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.034 (5)
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
C10.09584 (15)0.68653 (8)0.09659 (17)0.0409 (3)
C20.00451 (18)0.76411 (9)0.0806 (2)0.0486 (3)
C30.09684 (18)0.84004 (9)0.0908 (2)0.0489 (3)
C40.27626 (17)0.84136 (8)0.11443 (18)0.0432 (3)
C50.36672 (15)0.76343 (7)0.12846 (16)0.0357 (3)
C60.58366 (15)0.51923 (7)0.98574 (18)0.0387 (3)
N10.27389 (13)0.68927 (6)0.12240 (14)0.0367 (2)
N20.02268 (17)0.60827 (9)0.0867 (2)0.0545 (3)
N30.53983 (15)0.75560 (7)0.15032 (18)0.0438 (3)
O10.66072 (13)0.58252 (6)1.09322 (17)0.0616 (3)
O20.62758 (14)0.48268 (5)0.85337 (15)0.0534 (3)
O30.69012 (16)0.58577 (7)0.5533 (2)0.0588 (3)
H10.3288 (19)0.6390 (10)0.132 (2)0.047 (4)*
H20.121 (2)0.7616 (10)0.062 (2)0.060 (4)*
H30.035 (2)0.8950 (11)0.083 (2)0.059 (4)*
H40.341 (2)0.8932 (10)0.119 (2)0.055 (4)*
H2A0.094 (3)0.5626 (12)0.105 (3)0.073 (5)*
H2B0.087 (3)0.6040 (11)0.083 (2)0.064 (4)*
H3A0.579 (2)0.7043 (10)0.139 (2)0.051 (4)*
H3B0.594 (2)0.8023 (11)0.133 (2)0.057 (4)*
H3C0.636 (3)0.5645 (16)0.430 (4)0.107 (8)*
H3D0.671 (3)0.5480 (14)0.636 (3)0.088 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0343 (6)0.0543 (7)0.0344 (6)0.0032 (5)0.0145 (4)0.0062 (5)
C20.0352 (6)0.0671 (8)0.0452 (6)0.0074 (6)0.0185 (5)0.0016 (5)
C30.0517 (7)0.0522 (7)0.0456 (7)0.0163 (6)0.0230 (6)0.0027 (5)
C40.0479 (7)0.0409 (6)0.0423 (6)0.0042 (5)0.0202 (5)0.0007 (5)
C50.0365 (6)0.0408 (6)0.0306 (5)0.0007 (4)0.0149 (4)0.0013 (4)
C60.0377 (6)0.0331 (6)0.0482 (6)0.0030 (4)0.0206 (5)0.0029 (4)
N10.0335 (5)0.0389 (5)0.0381 (5)0.0011 (4)0.0154 (4)0.0035 (4)
N20.0398 (6)0.0584 (7)0.0678 (8)0.0112 (5)0.0248 (5)0.0129 (6)
N30.0388 (6)0.0411 (6)0.0566 (6)0.0005 (4)0.0248 (5)0.0002 (4)
O10.0480 (5)0.0533 (6)0.0903 (8)0.0141 (4)0.0356 (5)0.0240 (5)
O20.0689 (6)0.0423 (5)0.0696 (6)0.0005 (4)0.0492 (5)0.0005 (4)
O30.0701 (7)0.0524 (6)0.0601 (6)0.0087 (5)0.0331 (5)0.0021 (5)
Geometric parameters (Å, º) top
C1—N21.3346 (17)C6—O11.2343 (14)
C1—N11.3611 (15)C6—O21.2570 (14)
C1—C21.3862 (18)C6—C6i1.553 (2)
C2—C31.374 (2)N1—H10.882 (15)
C2—H20.958 (18)N2—H2A0.89 (2)
C3—C41.3762 (19)N2—H2B0.869 (19)
C3—H30.975 (16)N3—H3A0.871 (16)
C4—C51.3893 (16)N3—H3B0.877 (17)
C4—H40.950 (16)O3—H3C0.85 (3)
C5—N31.3351 (16)O3—H3D0.88 (2)
C5—N11.3586 (15)
N2—C1—N1116.62 (11)N1—C5—C4117.97 (11)
N2—C1—C2125.22 (11)O1—C6—O2125.98 (11)
N1—C1—C2118.16 (11)O1—C6—C6i117.66 (12)
C3—C2—C1118.85 (11)O2—C6—C6i116.36 (13)
C3—C2—H2123.6 (9)C5—N1—C1124.03 (10)
C1—C2—H2117.6 (9)C5—N1—H1119.5 (9)
C2—C3—C4122.07 (12)C1—N1—H1116.4 (9)
C2—C3—H3119.4 (9)C1—N2—H2A118.1 (12)
C4—C3—H3118.5 (9)C1—N2—H2B119.1 (11)
C3—C4—C5118.88 (12)H2A—N2—H2B122.1 (17)
C3—C4—H4123.1 (9)C5—N3—H3A118.1 (10)
C5—C4—H4118.0 (9)C5—N3—H3B117.1 (10)
N3—C5—N1117.07 (10)H3A—N3—H3B121.4 (15)
N3—C5—C4124.95 (11)H3C—O3—H3D105 (2)
N2—C1—C2—C3179.14 (12)C3—C4—C5—N11.32 (17)
N1—C1—C2—C30.16 (17)N3—C5—N1—C1178.61 (10)
C1—C2—C3—C40.6 (2)C4—C5—N1—C12.23 (16)
C2—C3—C4—C50.05 (19)N2—C1—N1—C5177.71 (10)
C3—C4—C5—N3179.60 (11)C2—C1—N1—C51.65 (17)
Symmetry code: (i) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2ii0.882 (15)1.911 (15)2.7611 (13)161.2 (13)
N2—H2A···O2ii0.89 (2)2.23 (2)3.0037 (17)145.2 (16)
N2—H2B···O1iii0.869 (19)2.079 (19)2.9445 (15)174.0 (16)
N3—H3A···O1iv0.871 (16)2.062 (17)2.9322 (15)176.7 (14)
N3—H3B···O3v0.877 (17)2.065 (17)2.9365 (16)172.3 (15)
O3—H3C···O1iv0.85 (3)2.47 (3)3.1418 (16)136 (2)
O3—H3C···O2ii0.85 (3)2.34 (2)3.1176 (16)152 (2)
O3—H3D···O20.88 (2)1.98 (2)2.8493 (15)168.9 (19)
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x1, y, z1; (iv) x, y, z1; (v) x, y+3/2, z1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds