In the title compound, 2C
5H
8N
3+·C
2O
22−·2H
2O, 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
CCDC reference: 624955
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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−·2H2O | F(000) = 364 |
Mr = 344.34 | Dx = 1.444 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 14420 reflections |
a = 8.0068 (6) Å | θ = 2.6–27.9° |
b = 15.4788 (8) Å | µ = 0.12 mm−1 |
c = 7.0250 (5) Å | T = 296 K |
β = 114.531 (6)° | Prism, light yellow |
V = 792.06 (9) Å3 | 0.65 × 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 focus | 1401 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.047 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.6° |
ω scans | h = −9→9 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −18→18 |
Tmin = 0.936, Tmax = 0.971 | l = −8→8 |
11192 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | All 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 reflections | Δρmax = 0.15 e Å−3 |
150 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.09584 (15) | 0.68653 (8) | 0.09659 (17) | 0.0409 (3) | |
C2 | 0.00451 (18) | 0.76411 (9) | 0.0806 (2) | 0.0486 (3) | |
C3 | 0.09684 (18) | 0.84004 (9) | 0.0908 (2) | 0.0489 (3) | |
C4 | 0.27626 (17) | 0.84136 (8) | 0.11443 (18) | 0.0432 (3) | |
C5 | 0.36672 (15) | 0.76343 (7) | 0.12846 (16) | 0.0357 (3) | |
C6 | 0.58366 (15) | 0.51923 (7) | 0.98574 (18) | 0.0387 (3) | |
N1 | 0.27389 (13) | 0.68927 (6) | 0.12240 (14) | 0.0367 (2) | |
N2 | 0.02268 (17) | 0.60827 (9) | 0.0867 (2) | 0.0545 (3) | |
N3 | 0.53983 (15) | 0.75560 (7) | 0.15032 (18) | 0.0438 (3) | |
O1 | 0.66072 (13) | 0.58252 (6) | 1.09322 (17) | 0.0616 (3) | |
O2 | 0.62758 (14) | 0.48268 (5) | 0.85337 (15) | 0.0534 (3) | |
O3 | 0.69012 (16) | 0.58577 (7) | 0.5533 (2) | 0.0588 (3) | |
H1 | 0.3288 (19) | 0.6390 (10) | 0.132 (2) | 0.047 (4)* | |
H2 | −0.121 (2) | 0.7616 (10) | 0.062 (2) | 0.060 (4)* | |
H3 | 0.035 (2) | 0.8950 (11) | 0.083 (2) | 0.059 (4)* | |
H4 | 0.341 (2) | 0.8932 (10) | 0.119 (2) | 0.055 (4)* | |
H2A | 0.094 (3) | 0.5626 (12) | 0.105 (3) | 0.073 (5)* | |
H2B | −0.087 (3) | 0.6040 (11) | 0.083 (2) | 0.064 (4)* | |
H3A | 0.579 (2) | 0.7043 (10) | 0.139 (2) | 0.051 (4)* | |
H3B | 0.594 (2) | 0.8023 (11) | 0.133 (2) | 0.057 (4)* | |
H3C | 0.636 (3) | 0.5645 (16) | 0.430 (4) | 0.107 (8)* | |
H3D | 0.671 (3) | 0.5480 (14) | 0.636 (3) | 0.088 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0343 (6) | 0.0543 (7) | 0.0344 (6) | −0.0032 (5) | 0.0145 (4) | −0.0062 (5) |
C2 | 0.0352 (6) | 0.0671 (8) | 0.0452 (6) | 0.0074 (6) | 0.0185 (5) | −0.0016 (5) |
C3 | 0.0517 (7) | 0.0522 (7) | 0.0456 (7) | 0.0163 (6) | 0.0230 (6) | 0.0027 (5) |
C4 | 0.0479 (7) | 0.0409 (6) | 0.0423 (6) | 0.0042 (5) | 0.0202 (5) | 0.0007 (5) |
C5 | 0.0365 (6) | 0.0408 (6) | 0.0306 (5) | 0.0007 (4) | 0.0149 (4) | −0.0013 (4) |
C6 | 0.0377 (6) | 0.0331 (6) | 0.0482 (6) | 0.0030 (4) | 0.0206 (5) | 0.0029 (4) |
N1 | 0.0335 (5) | 0.0389 (5) | 0.0381 (5) | 0.0011 (4) | 0.0154 (4) | −0.0035 (4) |
N2 | 0.0398 (6) | 0.0584 (7) | 0.0678 (8) | −0.0112 (5) | 0.0248 (5) | −0.0129 (6) |
N3 | 0.0388 (6) | 0.0411 (6) | 0.0566 (6) | 0.0005 (4) | 0.0248 (5) | 0.0002 (4) |
O1 | 0.0480 (5) | 0.0533 (6) | 0.0903 (8) | −0.0141 (4) | 0.0356 (5) | −0.0240 (5) |
O2 | 0.0689 (6) | 0.0423 (5) | 0.0696 (6) | −0.0005 (4) | 0.0492 (5) | −0.0005 (4) |
O3 | 0.0701 (7) | 0.0524 (6) | 0.0601 (6) | −0.0087 (5) | 0.0331 (5) | −0.0021 (5) |
Geometric parameters (Å, º) top
C1—N2 | 1.3346 (17) | C6—O1 | 1.2343 (14) |
C1—N1 | 1.3611 (15) | C6—O2 | 1.2570 (14) |
C1—C2 | 1.3862 (18) | C6—C6i | 1.553 (2) |
C2—C3 | 1.374 (2) | N1—H1 | 0.882 (15) |
C2—H2 | 0.958 (18) | N2—H2A | 0.89 (2) |
C3—C4 | 1.3762 (19) | N2—H2B | 0.869 (19) |
C3—H3 | 0.975 (16) | N3—H3A | 0.871 (16) |
C4—C5 | 1.3893 (16) | N3—H3B | 0.877 (17) |
C4—H4 | 0.950 (16) | O3—H3C | 0.85 (3) |
C5—N3 | 1.3351 (16) | O3—H3D | 0.88 (2) |
C5—N1 | 1.3586 (15) | | |
| | | |
N2—C1—N1 | 116.62 (11) | N1—C5—C4 | 117.97 (11) |
N2—C1—C2 | 125.22 (11) | O1—C6—O2 | 125.98 (11) |
N1—C1—C2 | 118.16 (11) | O1—C6—C6i | 117.66 (12) |
C3—C2—C1 | 118.85 (11) | O2—C6—C6i | 116.36 (13) |
C3—C2—H2 | 123.6 (9) | C5—N1—C1 | 124.03 (10) |
C1—C2—H2 | 117.6 (9) | C5—N1—H1 | 119.5 (9) |
C2—C3—C4 | 122.07 (12) | C1—N1—H1 | 116.4 (9) |
C2—C3—H3 | 119.4 (9) | C1—N2—H2A | 118.1 (12) |
C4—C3—H3 | 118.5 (9) | C1—N2—H2B | 119.1 (11) |
C3—C4—C5 | 118.88 (12) | H2A—N2—H2B | 122.1 (17) |
C3—C4—H4 | 123.1 (9) | C5—N3—H3A | 118.1 (10) |
C5—C4—H4 | 118.0 (9) | C5—N3—H3B | 117.1 (10) |
N3—C5—N1 | 117.07 (10) | H3A—N3—H3B | 121.4 (15) |
N3—C5—C4 | 124.95 (11) | H3C—O3—H3D | 105 (2) |
| | | |
N2—C1—C2—C3 | −179.14 (12) | C3—C4—C5—N1 | −1.32 (17) |
N1—C1—C2—C3 | 0.16 (17) | N3—C5—N1—C1 | −178.61 (10) |
C1—C2—C3—C4 | 0.6 (2) | C4—C5—N1—C1 | 2.23 (16) |
C2—C3—C4—C5 | −0.05 (19) | N2—C1—N1—C5 | 177.71 (10) |
C3—C4—C5—N3 | 179.60 (11) | C2—C1—N1—C5 | −1.65 (17) |
Symmetry code: (i) −x+1, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2ii | 0.882 (15) | 1.911 (15) | 2.7611 (13) | 161.2 (13) |
N2—H2A···O2ii | 0.89 (2) | 2.23 (2) | 3.0037 (17) | 145.2 (16) |
N2—H2B···O1iii | 0.869 (19) | 2.079 (19) | 2.9445 (15) | 174.0 (16) |
N3—H3A···O1iv | 0.871 (16) | 2.062 (17) | 2.9322 (15) | 176.7 (14) |
N3—H3B···O3v | 0.877 (17) | 2.065 (17) | 2.9365 (16) | 172.3 (15) |
O3—H3C···O1iv | 0.85 (3) | 2.47 (3) | 3.1418 (16) | 136 (2) |
O3—H3C···O2ii | 0.85 (3) | 2.34 (2) | 3.1176 (16) | 152 (2) |
O3—H3D···O2 | 0.88 (2) | 1.98 (2) | 2.8493 (15) | 168.9 (19) |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z−1; (iv) x, y, z−1; (v) x, −y+3/2, z−1/2. |