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In the crystal structure of the title compound, C12H10N22+·2NO3-, the 1,2-bis­(4-pyrid­yl)ethyl­ene cation is located on an inversion centre and is hydrogen bonded to the nitrate anion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040712/xu2137sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040712/xu2137Isup2.hkl
Contains datablock I

CCDC reference: 628433

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.118
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3
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, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
C12H12N22+·2NO3F(000) = 320
Mr = 308.26Dx = 1.517 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1257 reflections
a = 3.7654 (5) Åθ = 2.1–25.6°
b = 13.9364 (18) ŵ = 0.12 mm1
c = 12.8879 (16) ÅT = 273 K
β = 93.942 (2)°Block, white
V = 674.71 (15) Å30.38 × 0.29 × 0.25 mm
Z = 2
Data collection top
Bruker SMART CCD area detector
diffractometer
879 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
Graphite monochromatorθmax = 25.5°, θmin = 2.1°
φ and ω scansh = 44
3459 measured reflectionsk = 1616
1257 independent reflectionsl = 1514
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)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118 w = 1/[σ2(Fo2) + (0.0638P)2 + 0.0484P]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
1257 reflectionsΔρmax = 0.23 e Å3
105 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: none
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
C10.2201 (5)0.50227 (12)0.63902 (12)0.0422 (4)
C80.2536 (5)0.59778 (13)0.66872 (13)0.0528 (5)
H80.16420.64600.62440.063*
C20.3516 (5)0.43337 (13)0.70978 (14)0.0528 (5)
H20.33030.36860.69320.063*
C30.5122 (5)0.46055 (15)0.80380 (14)0.0562 (5)
H30.59930.41430.85090.067*
C40.4172 (5)0.62053 (14)0.76265 (14)0.0595 (6)
H40.44120.68470.78180.071*
N20.5434 (4)0.55281 (13)0.82752 (11)0.0549 (5)
C70.0604 (5)0.47144 (13)0.53723 (13)0.0492 (5)
H70.04400.40580.52490.059*
N30.9951 (4)0.30318 (11)0.99810 (11)0.0539 (5)
O31.0551 (4)0.39197 (9)0.99781 (9)0.0650 (5)
O10.8222 (5)0.26699 (9)0.92362 (12)0.0803 (5)
O21.1107 (5)0.25462 (10)1.07290 (12)0.0826 (5)
H1A0.675 (6)0.5751 (16)0.8926 (18)0.096 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0369 (9)0.0539 (11)0.0356 (9)0.0021 (8)0.0006 (7)0.0003 (7)
C80.0573 (12)0.0526 (11)0.0469 (10)0.0007 (9)0.0071 (9)0.0025 (8)
C20.0590 (12)0.0504 (11)0.0483 (10)0.0008 (9)0.0018 (9)0.0021 (8)
C30.0534 (12)0.0715 (13)0.0429 (10)0.0050 (10)0.0023 (9)0.0137 (9)
C40.0658 (14)0.0573 (12)0.0537 (12)0.0001 (10)0.0081 (10)0.0082 (9)
N20.0498 (10)0.0773 (12)0.0366 (8)0.0024 (8)0.0040 (7)0.0064 (8)
C70.0523 (12)0.0517 (11)0.0424 (10)0.0032 (8)0.0046 (8)0.0008 (7)
N30.0628 (11)0.0461 (9)0.0517 (9)0.0010 (8)0.0051 (8)0.0058 (7)
O30.0929 (11)0.0449 (8)0.0537 (8)0.0066 (7)0.0215 (7)0.0014 (6)
O10.0949 (12)0.0607 (9)0.0803 (10)0.0035 (8)0.0292 (9)0.0235 (8)
O20.1105 (14)0.0610 (9)0.0727 (10)0.0000 (8)0.0193 (9)0.0196 (8)
Geometric parameters (Å, º) top
C1—C81.388 (2)C4—N21.327 (2)
C1—C21.392 (2)C4—H40.9300
C1—C71.469 (2)N2—H1A0.99 (2)
C8—C41.357 (2)C7—C7i1.304 (3)
C8—H80.9300C7—H70.9300
C2—C31.370 (3)N3—O11.2304 (18)
C2—H20.9300N3—O21.2326 (19)
C3—N21.325 (3)N3—O31.2579 (19)
C3—H30.9300
C8—C1—C2117.34 (15)N2—C4—C8121.11 (18)
C8—C1—C7123.40 (15)N2—C4—H4119.4
C2—C1—C7119.25 (15)C8—C4—H4119.4
C4—C8—C1119.80 (17)C3—N2—C4121.50 (16)
C4—C8—H8120.1C3—N2—H1A121.9 (13)
C1—C8—H8120.1C4—N2—H1A116.5 (13)
C3—C2—C1120.29 (17)C7i—C7—C1125.4 (2)
C3—C2—H2119.9C7i—C7—H7117.3
C1—C2—H2119.9C1—C7—H7117.3
N2—C3—C2119.95 (17)O1—N3—O2121.64 (17)
N2—C3—H3120.0O1—N3—O3119.11 (15)
C2—C3—H3120.0O2—N3—O3119.25 (15)
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1A···O3ii0.99 (2)1.74 (2)2.7344 (19)174 (2)
C3—H3···O10.932.393.283 (2)162
Symmetry code: (ii) x+2, y+1, z+2.
 

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