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The title compound, C10H9N2+·I3, contains monoprotonated 4,4′-bipyridinium cations and triiodide anions. The cations assemble into infinite chains by way of N—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047623/hb2197sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047623/hb2197Isup2.hkl
Contains datablock I

CCDC reference: 629886

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.036
  • wR factor = 0.079
  • Data-to-parameter ratio = 38.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.27 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.42
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 0 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 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: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXL97.

4-(4-Pyridyl)pyridinium triiodide top
Crystal data top
C10H9N2+·I3Z = 2
Mr = 537.89F(000) = 484
Triclinic, P1Dx = 2.649 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8399 (9) ÅCell parameters from 3150 reflections
b = 9.6529 (8) Åθ = 3.6–36.6°
c = 9.7154 (7) ŵ = 6.93 mm1
α = 107.743 (7)°T = 100 K
β = 104.709 (7)°Prism, yellow–brown
γ = 110.791 (8)°0.12 × 0.06 × 0.06 mm
V = 674.38 (13) Å3
Data collection top
Kuma KM-4-CCD
diffractometer
5192 independent reflections
Radiation source: fine-focus sealed tube3429 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
ω scansθmax = 36.6°, θmin = 3.6°
Absorption correction: numerical
(CrysAlis RED; Oxford Diffraction, 2003)
h = 1411
Tmin = 0.490, Tmax = 0.681k = 1515
10483 measured reflectionsl = 1416
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)] = 0.036Hydrogen site location: difmap and geom
wR(F2) = 0.079H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.0339P)2]
where P = (Fo2 + 2Fc2)/3
5192 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 3.20 e Å3
0 restraintsΔρmin = 1.41 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.7381 (5)0.5423 (4)0.0037 (4)0.0161 (8)
H1A0.74220.44030.00070.019*
N20.7301 (5)1.2664 (4)0.0020 (4)0.0150 (7)
C10.8532 (6)0.6894 (5)0.1275 (5)0.0173 (9)
H10.93610.69460.21570.021*
C20.8532 (6)0.8338 (5)0.1291 (5)0.0167 (9)
H20.93560.93690.21720.020*
C30.6215 (6)0.5334 (5)0.1223 (5)0.0163 (8)
H30.54240.42900.20990.020*
C40.6135 (6)0.6719 (5)0.1282 (5)0.0157 (8)
H40.52930.66290.21820.019*
C50.6827 (6)0.9944 (5)0.1419 (5)0.0162 (8)
H50.64920.90600.23980.019*
C60.6885 (6)1.1418 (5)0.1375 (5)0.0165 (8)
H60.66241.15420.23270.020*
C70.7686 (6)1.1095 (5)0.1399 (5)0.0148 (8)
H70.79631.10140.23730.018*
C80.7689 (6)1.2505 (5)0.1342 (5)0.0157 (8)
H80.79751.33970.22940.019*
C90.7262 (6)0.9774 (5)0.0019 (5)0.0128 (8)
C100.7311 (5)0.8257 (5)0.0002 (5)0.0137 (8)
I10.23357 (4)0.32624 (3)0.47599 (3)0.01487 (6)
I20.26742 (4)0.05081 (3)0.52739 (3)0.01641 (7)
I30.22289 (4)0.61395 (3)0.43887 (3)0.01844 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.026 (2)0.0093 (15)0.0189 (18)0.0115 (15)0.0100 (15)0.0085 (14)
N20.0185 (17)0.0099 (15)0.0161 (17)0.0061 (13)0.0058 (14)0.0068 (13)
C10.021 (2)0.0152 (19)0.016 (2)0.0105 (17)0.0020 (16)0.0090 (15)
C20.023 (2)0.0113 (18)0.0149 (19)0.0081 (16)0.0060 (16)0.0060 (15)
C30.021 (2)0.0097 (17)0.0150 (19)0.0066 (16)0.0041 (16)0.0043 (14)
C40.019 (2)0.0130 (18)0.0152 (19)0.0096 (16)0.0046 (16)0.0065 (15)
C50.023 (2)0.0160 (19)0.0140 (19)0.0131 (17)0.0072 (16)0.0083 (15)
C60.021 (2)0.0155 (19)0.015 (2)0.0114 (17)0.0050 (16)0.0076 (16)
C70.020 (2)0.0094 (17)0.0134 (18)0.0066 (15)0.0041 (15)0.0047 (14)
C80.020 (2)0.0124 (18)0.0143 (19)0.0094 (16)0.0066 (16)0.0044 (14)
C90.0163 (18)0.0063 (16)0.0178 (19)0.0067 (15)0.0066 (15)0.0064 (14)
C100.016 (2)0.0145 (18)0.016 (2)0.0098 (16)0.0064 (16)0.0101 (15)
I10.01617 (13)0.01307 (11)0.01417 (12)0.00690 (10)0.00475 (10)0.00561 (9)
I20.02006 (14)0.01468 (13)0.01560 (13)0.00868 (10)0.00629 (10)0.00807 (10)
I30.02265 (15)0.01595 (13)0.02152 (15)0.01120 (11)0.00981 (11)0.01070 (11)
Geometric parameters (Å, º) top
N1—C31.342 (6)C4—H40.9500
N1—C11.345 (5)C5—C61.392 (6)
N1—H1A0.9902C5—C91.393 (6)
N2—C61.338 (5)C5—H50.9500
N2—C81.350 (6)C6—H60.9500
C1—C21.390 (6)C7—C81.378 (6)
C1—H10.9500C7—C91.412 (5)
C2—C101.391 (6)C7—H70.9500
C2—H20.9500C8—H80.9500
C3—C41.382 (6)C9—C101.486 (5)
C3—H30.9500I1—I32.9380 (5)
C4—C101.399 (6)I1—I22.9505 (5)
C3—N1—C1119.9 (4)C9—C5—H5120.2
C3—N1—H1A118.8N2—C6—C5121.5 (4)
C1—N1—H1A121.1N2—C6—H6119.3
C6—N2—C8119.7 (4)C5—C6—H6119.3
N1—C1—C2121.3 (4)C8—C7—C9118.7 (4)
N1—C1—H1119.3C8—C7—H7120.7
C2—C1—H1119.3C9—C7—H7120.7
C1—C2—C10119.2 (4)N2—C8—C7122.3 (4)
C1—C2—H2120.4N2—C8—H8118.9
C10—C2—H2120.4C7—C8—H8118.9
N1—C3—C4121.8 (4)C5—C9—C7118.3 (4)
N1—C3—H3119.1C5—C9—C10121.4 (4)
C4—C3—H3119.1C7—C9—C10120.3 (4)
C3—C4—C10119.0 (4)C2—C10—C4118.7 (4)
C3—C4—H4120.5C2—C10—C9120.7 (4)
C10—C4—H4120.5C4—C10—C9120.6 (4)
C6—C5—C9119.5 (4)I3—I1—I2176.443 (13)
C6—C5—H5120.2
 

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