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In the title compound, C12H16N42+·2Br, the mol­ecule has a centre of symmetry at the mid-point of the central C—C bond and a mirror plane passes through the amino N atom, the attached C atom, the ring N atom, and the linking chain C atom; the Br anion lies on a position of site symmetry m. The two pyridyl rings are parallel to each other.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007975/wn2010sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007975/wn2010Isup2.hkl
Contains datablock I

CCDC reference: 605208

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.056
  • wR factor = 0.157
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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, 1997); software used to prepare material for publication: SHELXTL.

1,1'-ethylenebis(4-aminopyridinium) dibromide top
Crystal data top
C12H16N42+·2BrF(000) = 372
Mr = 376.11Dx = 1.799 Mg m3
Monoclinic, C2/mMelting point: 451 K
Hall symbol: -C 2yMo Kα radiation, λ = 0.71073 Å
a = 13.121 (4) ÅCell parameters from 1061 reflections
b = 6.4876 (19) Åθ = 3.2–26.2°
c = 8.406 (2) ŵ = 5.83 mm1
β = 104.023 (5)°T = 294 K
V = 694.2 (4) Å3Block, colorless
Z = 20.32 × 0.22 × 0.18 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
758 independent reflections
Radiation source: fine-focus sealed tube638 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 26.2°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1614
Tmin = 0.214, Tmax = 0.350k = 87
1850 measured reflectionsl = 107
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0778P)2 + 6.17P]
where P = (Fo2 + 2Fc2)/3
758 reflections(Δ/σ)max < 0.001
52 parametersΔρmax = 1.52 e Å3
0 restraintsΔρmin = 0.93 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*/UeqOcc. (<1)
N10.3254 (8)0.00000.2149 (10)0.044 (2)
H1A0.323 (6)0.111 (12)0.265 (10)0.053*
N20.4139 (6)0.00000.2871 (8)0.0321 (16)
C10.3581 (7)0.00000.0528 (10)0.0316 (19)
C20.3752 (5)0.1845 (10)0.0379 (8)0.0375 (15)
H20.36820.31050.01630.045*
C30.4019 (6)0.1790 (10)0.2043 (8)0.0393 (15)
H30.41210.30230.26240.047*
C60.4414 (8)0.00000.4675 (10)0.036 (2)
H6A0.41170.12100.50700.044*0.50
H6B0.41170.12100.50700.044*0.50
Br10.14890 (9)0.00000.36179 (12)0.0437 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.058 (6)0.043 (5)0.034 (4)0.0000.018 (4)0.000
N20.032 (4)0.036 (4)0.032 (4)0.0000.014 (3)0.000
C10.024 (5)0.038 (5)0.037 (4)0.0000.016 (4)0.000
C20.043 (4)0.030 (3)0.041 (3)0.002 (3)0.012 (3)0.006 (3)
C30.050 (4)0.028 (3)0.041 (3)0.001 (3)0.015 (3)0.004 (3)
C60.036 (5)0.045 (5)0.030 (4)0.0000.011 (4)0.000
Br10.0523 (8)0.0311 (5)0.0491 (6)0.0000.0149 (5)0.000
Geometric parameters (Å, º) top
N1—C11.325 (12)C2—C31.358 (9)
N1—H1A0.83 (8)C2—H20.9300
N2—C31.344 (7)C3—H30.9300
N2—C3i1.344 (7)C6—C6ii1.503 (19)
N2—C61.471 (11)C6—H6A0.9700
C1—C21.408 (8)C6—H6B0.9700
C1—C2i1.408 (8)
C1—N1—H1A119 (6)N2—C3—C2121.7 (6)
C3—N2—C3i119.6 (7)N2—C3—H3119.2
C3—N2—C6120.2 (4)C2—C3—H3119.2
C3i—N2—C6120.2 (4)N2—C6—C6ii110.4 (9)
N1—C1—C2121.8 (4)N2—C6—H6A109.6
N1—C1—C2i121.8 (4)C6ii—C6—H6A109.6
C2—C1—C2i116.5 (8)N2—C6—H6B109.6
C3—C2—C1120.2 (6)C6ii—C6—H6B109.6
C3—C2—H2119.9H6A—C6—H6B108.1
C1—C2—H2119.9
N1—C1—C2—C3175.5 (8)C1—C2—C3—N20.8 (11)
C2i—C1—C2—C33.0 (12)C3—N2—C6—C6ii89.6 (7)
C3i—N2—C3—C21.6 (13)C3i—N2—C6—C6ii89.6 (7)
C6—N2—C3—C2179.1 (7)
Symmetry codes: (i) x, y, z; (ii) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Br1iii0.83 (8)2.70 (8)3.516 (3)166 (7)
Symmetry code: (iii) x+1/2, y1/2, z.
 

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