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The title structure, C10H8N2·C6F4I2, is formed by two independent, nearly perpendicular, wave-like chains of bi­pyridine...1,2-di­iodo­tetra­fluoro­benzene adducts, extended throughout the whole crystal, linked by four independent I...N halogen bonds, ranging in length between 2.909 (5) and 2.964 (5) Å and C—I...N angles between 172.1 (2) and 176.2 (2)°. The second structural motif is a number of H...F hydrogen interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802007201/na6158sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802007201/na6158Isup2.hkl
Contains datablock I

CCDC reference: 185805

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.038
  • wR factor = 0.094
  • Data-to-parameter ratio = 15.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_731 Alert C Bond Calc 0.93(5), Rep 0.94(2) .... 2.50 s.u-Ratio C2C -H2C 1.555 1.555 PLAT_731 Alert C Bond Calc 0.93(5), Rep 0.93(2) .... 2.50 s.u-Ratio C2D -H2D 1.555 1.555 PLAT_731 Alert C Bond Calc 0.94(5), Rep 0.93(2) .... 2.50 s.u-Ratio C5D -H5D 1.555 1.555 PLAT_735 Alert C D-H Calc 0.93(5), Rep 0.94(2) .... 2.50 s.u-Ratio C2C -H2C 1.555 1.555 PLAT_735 Alert C D-H Calc 0.93(5), Rep 0.93(2) .... 2.50 s.u-Ratio C2D -H2D 1.555 1.555 General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.673 Tmax scaled 0.662 Tmin scaled 0.450
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
5 Alert Level C = Please check

Comment top

The title structure determination, (I), is part of a study on the halogen bond, which is a powerful intermolecular interaction we have extensively used to produce a variety of structures involving perfluorinated compounds (Cardillo et al., 2000), usually very difficult to crystallize.

In the present structure, 1,2-diiodotetrafluorobenzene (F4dIb) behaves as a bidentate acceptor, as well as 1,4-diiodotetrafluorobenzene, with the same base (Bailey Walsh et al., 2001), towards 4,4'-bipyridine (4,4'-bpy), giving rise to chains extended along the whole crystal, in which the two modules alternate with a 1:1 ratio.

The asymmetric unit contains two independent 4,4'-bpy···F4dIb aggregates, linked by I···N halogen bonds (see Fig. 1). We have assigned the same numbering scheme to chemically equivalent molecules, which are distinguished by the suffix (A and B for F4dIb, and C and D for 4,4'-bpy). The basic aggregates behave as monomers in building two independent, infinite, wave-like chains, in which the F4dIbs represent the crests and 4,4'-bpys the walls; Fig. 2(a) shows a single chain B···D···; the wave A···C··· has the same aspect.

The only strong intermolecular interaction is represented by four independent I···N intermolecular contacts: I1A···N4C 2.928 (4), I1B···N4D 2.909 (5), I2A···N10Ci 2.958 (4) [symmetry code: (i) x, -1/2 - y, -1/2 + z] and I2B···N10Dii 2.964 (5) Å [symmetry code: (ii) -1/2 + x, 1 - y, z]; these distances are not particularly short, if compared, for example, to 2.810 (5) Å found between 1,2-bis(4-pyridyl)ethylene and 1,4-diiodotetrafluorobenzene (Bailey Walsh et al., 2001); the relative C—I···N angles deviate a little from linearity, ranging from 172.1 (2) to 176.2 (2)°.

Within any wave, F4dIbs and 4,4'-bpys are mutually perpendicular because of the second structural motif, namely some H···F contacts shorter than the sum of van der Waals radii (2.7 Å); these attractive interactions, reported in Table 1, act between couples of independent waves. To better understand how these interactions work, see Fig. 2 and 3.

Fig. 2(b) shows the same wave B···D··· projected along c axis as in Fig. 2(a), together a second one related by a screw axis. As can be seen, the two waves, in projections, form large ellipses. In contrast to what would seem from this figure and the following ones, no ππ interaction contributes to the stabilization of the structure; the distance between the partially overlapping F4dIbs in Fig. 2(b) is about 7 Å. Fig. 3 shows the two ways of insertion of the waves A···C··· into the ellipses.

At the bottom, a wave is slipped into the middle of the ellipse; 4,4'-bpyCs are placed exactly at the level of F4dIbBs and form H···F interactions parallel to the sheet, shown as dotted lines. These interactions force the 4,4'-bpyC to be about coplanar with the F4dIbB. The second type of insertion of the wave A···C··· is shown in the top ellipse. Here, two H···F interactions are perpendicular to the sheet and bind 4,4'-bpyD to F4dIbA. BpyD and F4dIbA are also about coplanar.

Figs. 4 and 5 show the whole content of an unit cell viewed along c and b, respectively; it is quite difficult from these two plots to appreciate the contributes to the stability of the structure.

Dunitz & Taylor, (1997) titled their paper `Organic fluorine hardly ever accepts hydrogen bonds'. This is surely true if there is the possibilty of stronger interactions but, in this case, H···F interactions seem quite remarkable for the structure assemblage.

Experimental top

The starting materials were commercial batchs from Aldrich and Apollo Scientific Ltd. The analysed infinite network was obtained by dissolving in chloroform, at room temperature and in a vial, equimolecular amounts of 4,4'-bpy and F4dIb. The open vial was closed in a cylindrical bottle containing vaseline oil. Volatile solvents were allowed to diffuse at room temperature and after one day the formed crystals were filtered and washed with carbon tetrachloride. M.p. 411–413 K; I·R. (KBr/ν/cm-1, selected bands): 3042, 1592, 1483, 1429, 1407, 1218, 1009, 803, 612. Crystals were obtained as large plastic prisms.

Refinement top

A first data collection on a cut crystal permitted the structure resolution, but the refinement was unsatisfactory, probably because the crystal had a very large mosaic spread due to the cut deformation. To prevent such phenomenon the crystal used for the second data collection was reduced by a partial dissolution in chloroform. H atoms were refined by imposing soft geometric restraints on C—H and closest intramolecular H···H distances. The structure may be described in the standard space group C2/c with a very large β (129.35°), so we preferred the I2/a description. Two diagonals of the I2/a monoclinic cell are the axes of a pseudo-orthorhombic F cell (a = 18.227, b = 33.714, c = 22.045 Å, α = 90.00, b = 89.60, γ = 90.00°), but the Laue symmetry is not orthorhombic, because an attempt to merge the data gave Rave = 0.337.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett and Johnson, 1996); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983).

Figures top
[Figure 1] Fig. 1. The molecular plot of indepent molecules with the atom-numbering scheme, showing 50% probability displacement ellipsoids. H atoms are not shown to scale. Dashed lines represent the halogen bond
[Figure 2] Fig. 2. (a) A wave of 4,4'-bpyB···F4dIbD··· projected along the c axis. (b) The same wave together a second one related by a screw axis.
[Figure 3] Fig. 3. As Fig. 2(b), with the addition of two waves 4,4'-bpyA···F4dIbC··· about perpendicular to the sheet showing H···F interactions as dotted lines.
[Figure 4] Fig. 4. The complete packing view along c axis.
[Figure 5] Fig. 5. The packing draw viewed along b axis.
4,4'-bipyridine 1,2-diiodotetrafluorobenzene top
Crystal data top
C10H8N2·C6F4I2F(000) = 4160
Mr = 558.04Dx = 2.189 Mg m3
Monoclinic, I2/aMo Kα radiation, λ = 0.71069 Å
a = 14.2535 (10) ÅCell parameters from 2996 reflections
b = 33.714 (3) Åθ = 3.1–27.3°
c = 14.3511 (12) ŵ = 3.75 mm1
β = 100.831 (6)°T = 290 K
V = 6773.5 (10) Å3Elongated prism with rounded edges, colourless
Z = 160.40 × 0.16 × 0.11 mm
Data collection top
Bruker SMART-APEX CCD area-detector
diffractometer
7796 independent reflections
Radiation source: fine-focus sealed tube5552 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ω and ϕ scansθmax = 27.5°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 1818
Tmin = 0.668, Tmax = 0.983k = 4343
15718 measured reflectionsl = 1818
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)] = 0.039All H-atom parameters refined
wR(F2) = 0.094
S = 0.97(Δ/σ)max = 0.008
7796 reflectionsΔρmax = 0.66 e Å3
498 parametersΔρmin = 0.60 e Å3
148 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.000218 (18)
Crystal data top
C10H8N2·C6F4I2V = 6773.5 (10) Å3
Mr = 558.04Z = 16
Monoclinic, I2/aMo Kα radiation
a = 14.2535 (10) ŵ = 3.75 mm1
b = 33.714 (3) ÅT = 290 K
c = 14.3511 (12) Å0.40 × 0.16 × 0.11 mm
β = 100.831 (6)°
Data collection top
Bruker SMART-APEX CCD area-detector
diffractometer
7796 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
5552 reflections with I > 2σ(I)
Tmin = 0.668, Tmax = 0.983Rint = 0.018
15718 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039148 restraints
wR(F2) = 0.094All H-atom parameters refined
S = 0.97Δρmax = 0.66 e Å3
7796 reflectionsΔρmin = 0.60 e Å3
498 parameters
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
I1A0.11176 (2)0.066462 (9)0.00530 (2)0.06253 (11)
I2A0.13725 (2)0.070509 (9)0.24644 (2)0.06673 (12)
C1A0.1257 (3)0.01598 (12)0.0766 (3)0.0513 (10)
C2A0.1319 (3)0.01726 (12)0.1718 (3)0.0536 (10)
C3A0.1374 (3)0.01814 (14)0.2194 (3)0.0625 (12)
C4A0.1387 (4)0.05432 (14)0.1745 (4)0.0693 (13)
C5A0.1353 (3)0.05542 (14)0.0813 (4)0.0685 (13)
C6A0.1288 (3)0.02103 (14)0.0325 (3)0.0578 (11)
F1A0.1406 (2)0.01814 (9)0.3133 (2)0.0876 (9)
F2A0.1437 (3)0.08798 (9)0.2232 (3)0.0994 (11)
F3A0.1390 (2)0.09058 (8)0.0361 (3)0.0946 (10)
F4A0.1258 (2)0.02359 (8)0.0602 (2)0.0795 (8)
I1B0.26220 (3)0.316354 (11)0.13789 (2)0.07917 (13)
I2B0.00046 (3)0.321219 (10)0.11299 (3)0.07737 (13)
C1B0.1751 (4)0.26572 (14)0.1216 (3)0.0607 (12)
C2B0.0771 (4)0.26780 (14)0.1153 (3)0.0630 (12)
C3B0.0255 (4)0.23284 (16)0.1093 (3)0.0693 (14)
C4B0.0700 (5)0.19652 (16)0.1076 (4)0.0812 (16)
C5B0.1644 (5)0.19500 (16)0.1092 (4)0.0824 (17)
C6B0.2175 (4)0.22931 (17)0.1167 (3)0.0721 (14)
F1B0.0691 (2)0.23280 (10)0.1039 (2)0.1005 (10)
F2B0.0179 (3)0.16290 (10)0.1029 (3)0.1141 (13)
F3B0.2078 (3)0.15950 (11)0.1063 (3)0.1204 (13)
F4B0.3114 (3)0.22600 (11)0.1226 (3)0.1086 (11)
C1C0.1257 (3)0.22460 (12)0.1298 (3)0.0552 (11)
C2C0.2039 (4)0.20170 (15)0.1204 (5)0.0777 (15)
H2C0.259 (3)0.2142 (13)0.109 (5)0.13 (3)*
C3C0.1938 (5)0.16080 (16)0.1106 (5)0.0832 (16)
H3C0.246 (2)0.1459 (11)0.102 (4)0.074 (15)*
N4C0.1127 (4)0.14178 (12)0.1070 (3)0.0765 (12)
C5C0.0376 (5)0.16376 (16)0.1160 (4)0.0797 (15)
H5C0.015 (2)0.1473 (10)0.108 (3)0.064 (14)*
C6C0.0412 (4)0.20463 (15)0.1275 (4)0.0712 (13)
H6C0.018 (2)0.2155 (12)0.129 (4)0.11 (2)*
C7C0.1314 (3)0.26822 (13)0.1404 (3)0.0557 (11)
C8C0.2084 (4)0.28952 (15)0.1227 (4)0.0711 (14)
H8C0.262 (2)0.2758 (12)0.111 (4)0.092 (18)*
C9C0.2095 (5)0.33094 (16)0.1349 (5)0.0805 (16)
H9C0.258 (3)0.3445 (11)0.114 (3)0.081 (17)*
N10C0.1406 (4)0.35109 (12)0.1617 (3)0.0785 (12)
C11C0.0686 (5)0.33047 (17)0.1783 (5)0.0863 (17)
H11C0.017 (3)0.3434 (12)0.193 (4)0.10 (2)*
C12C0.0592 (4)0.28959 (15)0.1694 (4)0.0719 (14)
H12C0.007 (2)0.2751 (12)0.181 (4)0.094 (19)*
C7D0.3859 (3)0.51815 (13)0.1222 (3)0.0582 (11)
C12D0.3969 (5)0.54285 (17)0.1992 (4)0.0787 (15)
H12D0.396 (4)0.5273 (12)0.252 (2)0.11 (2)*
C11D0.4050 (5)0.58305 (19)0.1880 (5)0.0941 (19)
H11D0.408 (4)0.5955 (11)0.246 (2)0.089 (18)*
N10D0.4042 (4)0.60067 (13)0.1079 (4)0.0890 (14)
C9D0.3940 (7)0.57799 (19)0.0334 (5)0.109 (2)
H9D0.382 (4)0.5866 (13)0.0289 (19)0.10 (2)*
C8D0.3830 (5)0.53684 (17)0.0368 (4)0.0894 (19)
H8D0.375 (4)0.5185 (12)0.012 (3)0.11 (2)*
C1D0.3767 (3)0.47456 (14)0.1296 (3)0.0579 (11)
C2D0.3811 (5)0.44943 (17)0.0553 (4)0.0891 (18)
H2D0.377 (7)0.4621 (16)0.003 (3)0.19 (4)*
C3D0.3725 (6)0.40885 (18)0.0681 (5)0.099 (2)
H3D0.373 (4)0.3940 (14)0.014 (3)0.11 (2)*
N4D0.3611 (3)0.39215 (14)0.1472 (4)0.0886 (14)
C5D0.3587 (5)0.4164 (2)0.2187 (6)0.097 (2)
H5D0.341 (5)0.4024 (14)0.269 (3)0.15 (3)*
C6D0.3660 (5)0.45641 (19)0.2124 (4)0.0853 (17)
H6D0.365 (4)0.4703 (12)0.268 (2)0.11 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I1A0.0595 (2)0.05304 (19)0.0771 (2)0.00581 (13)0.01808 (16)0.01005 (14)
I2A0.0715 (2)0.05309 (19)0.0739 (2)0.00423 (15)0.00944 (17)0.01075 (15)
C1A0.043 (2)0.044 (2)0.067 (3)0.0038 (18)0.011 (2)0.002 (2)
C2A0.045 (2)0.046 (2)0.068 (3)0.0035 (18)0.007 (2)0.005 (2)
C3A0.065 (3)0.053 (3)0.071 (3)0.001 (2)0.015 (2)0.003 (2)
C4A0.069 (3)0.048 (3)0.093 (4)0.002 (2)0.019 (3)0.007 (3)
C5A0.063 (3)0.042 (3)0.102 (4)0.001 (2)0.017 (3)0.007 (3)
C6A0.054 (3)0.056 (3)0.064 (3)0.003 (2)0.013 (2)0.005 (2)
F1A0.115 (3)0.079 (2)0.0711 (18)0.0037 (17)0.0232 (17)0.0097 (15)
F2A0.120 (3)0.0536 (17)0.129 (3)0.0027 (17)0.035 (2)0.0256 (18)
F3A0.103 (2)0.0512 (17)0.131 (3)0.0013 (15)0.028 (2)0.0254 (17)
F4A0.091 (2)0.0762 (19)0.0731 (18)0.0130 (16)0.0192 (16)0.0142 (15)
I1B0.0874 (3)0.0814 (3)0.0643 (2)0.02539 (19)0.00273 (18)0.01359 (17)
I2B0.0909 (3)0.0667 (2)0.0743 (2)0.00258 (18)0.01497 (19)0.00712 (17)
C1B0.077 (3)0.061 (3)0.040 (2)0.013 (2)0.002 (2)0.006 (2)
C2B0.084 (4)0.060 (3)0.044 (2)0.013 (3)0.008 (2)0.006 (2)
C3B0.076 (4)0.073 (4)0.056 (3)0.020 (3)0.004 (3)0.009 (2)
C4B0.119 (5)0.060 (3)0.063 (3)0.023 (3)0.011 (3)0.001 (3)
C5B0.130 (6)0.058 (3)0.060 (3)0.010 (4)0.019 (3)0.002 (2)
C6B0.083 (4)0.078 (4)0.055 (3)0.007 (3)0.013 (3)0.001 (3)
F1B0.085 (2)0.099 (2)0.114 (3)0.0256 (19)0.013 (2)0.012 (2)
F2B0.158 (3)0.067 (2)0.109 (3)0.038 (2)0.003 (2)0.0007 (18)
F3B0.180 (4)0.074 (2)0.107 (3)0.028 (2)0.026 (3)0.008 (2)
F4B0.096 (3)0.115 (3)0.120 (3)0.018 (2)0.034 (2)0.009 (2)
C1C0.072 (3)0.043 (2)0.050 (2)0.002 (2)0.009 (2)0.0005 (19)
C2C0.072 (4)0.047 (3)0.113 (4)0.001 (3)0.015 (3)0.008 (3)
C3C0.094 (4)0.051 (3)0.102 (4)0.017 (3)0.011 (4)0.002 (3)
N4C0.097 (3)0.047 (2)0.083 (3)0.003 (2)0.012 (3)0.002 (2)
C5C0.098 (4)0.053 (3)0.089 (4)0.021 (3)0.019 (3)0.008 (3)
C6C0.074 (4)0.057 (3)0.088 (4)0.002 (3)0.029 (3)0.007 (3)
C7C0.069 (3)0.044 (2)0.055 (2)0.001 (2)0.013 (2)0.0011 (19)
C8C0.076 (3)0.055 (3)0.087 (4)0.000 (3)0.025 (3)0.008 (3)
C9C0.087 (4)0.051 (3)0.110 (4)0.009 (3)0.032 (4)0.012 (3)
N10C0.100 (4)0.044 (2)0.094 (3)0.002 (2)0.024 (3)0.007 (2)
C11C0.109 (5)0.057 (3)0.099 (4)0.018 (3)0.035 (4)0.009 (3)
C12C0.081 (4)0.057 (3)0.081 (3)0.000 (3)0.023 (3)0.007 (3)
C7D0.056 (3)0.052 (3)0.068 (3)0.001 (2)0.017 (2)0.005 (2)
C12D0.100 (4)0.068 (4)0.070 (3)0.000 (3)0.021 (3)0.006 (3)
C11D0.121 (5)0.068 (4)0.090 (4)0.005 (4)0.014 (4)0.027 (4)
N10D0.105 (4)0.054 (3)0.108 (4)0.004 (2)0.021 (3)0.010 (3)
C9D0.185 (8)0.059 (4)0.081 (4)0.009 (4)0.022 (5)0.005 (3)
C8D0.144 (6)0.059 (3)0.070 (3)0.006 (3)0.033 (4)0.007 (3)
C1D0.050 (3)0.058 (3)0.068 (3)0.004 (2)0.017 (2)0.001 (2)
C2D0.132 (5)0.059 (3)0.075 (4)0.019 (3)0.015 (4)0.005 (3)
C3D0.140 (6)0.057 (3)0.094 (5)0.018 (4)0.005 (4)0.010 (3)
N4D0.085 (3)0.066 (3)0.113 (4)0.014 (2)0.014 (3)0.013 (3)
C5D0.111 (5)0.078 (4)0.113 (5)0.010 (4)0.056 (4)0.027 (4)
C6D0.099 (4)0.081 (4)0.086 (4)0.006 (3)0.044 (4)0.005 (3)
Geometric parameters (Å, º) top
I1A—C1A2.099 (4)C5C—C6C1.388 (7)
I1A—N4C2.928 (4)C5C—H5C0.92 (2)
I2A—C2A2.099 (4)C6C—H6C0.93 (2)
I2A—N10Ci2.958 (4)C7C—C8C1.375 (7)
C1A—C2A1.387 (6)C7C—C12C1.382 (7)
C1A—C6A1.396 (6)C8C—C9C1.407 (7)
C2A—C3A1.385 (6)C8C—H8C0.93 (2)
C3A—F1A1.357 (5)C9C—N10C1.309 (7)
C3A—C4A1.378 (7)C9C—H9C0.93 (2)
C4A—F2A1.342 (6)N10C—C11C1.299 (7)
C4A—C5A1.348 (8)N10C—I2Aiii2.958 (4)
C5A—F3A1.347 (5)C11C—C12C1.388 (8)
C5A—C6A1.366 (7)C11C—H11C0.92 (2)
C6A—F4A1.342 (5)C12C—H12C0.93 (2)
I1B—C1B2.098 (5)C7D—C12D1.369 (7)
I1B—N4D2.909 (5)C7D—C8D1.372 (7)
I2B—C2B2.103 (5)C7D—C1D1.481 (6)
I2B—N10Dii2.964 (5)C12D—C11D1.372 (8)
C1B—C6B1.376 (7)C12D—H12D0.92 (2)
C1B—C2B1.385 (7)C11D—N10D1.292 (8)
C2B—C3B1.383 (6)C11D—H11D0.92 (2)
C3B—F1B1.336 (6)N10D—C9D1.300 (8)
C3B—C4B1.382 (8)N10D—I2Biv2.964 (5)
C4B—C5B1.342 (9)C9D—C8D1.398 (8)
C4B—F2B1.350 (6)C9D—H9D0.92 (2)
C5B—F3B1.351 (6)C8D—H8D0.92 (2)
C5B—C6B1.375 (8)C1D—C6D1.370 (7)
C6B—F4B1.330 (6)C1D—C2D1.373 (7)
C1C—C6C1.375 (7)C2D—C3D1.389 (8)
C1C—C2C1.382 (7)C2D—H2D0.93 (2)
C1C—C7C1.479 (6)C3D—N4D1.304 (8)
C2C—C3C1.391 (7)C3D—H3D0.93 (2)
C2C—H2C0.94 (2)N4D—C5D1.317 (8)
C3C—N4C1.314 (7)C5D—C6D1.357 (9)
C3C—H3C0.93 (2)C5D—H5D0.93 (2)
N4C—C5C1.328 (7)C6D—H6D0.92 (2)
C1A—I1A—N4C172.09 (15)N4C—C5C—H5C107 (3)
N4C—I1A—C6A160.85 (12)C6C—C5C—H5C129 (3)
C2A—I2A—N10Ci175.37 (16)C1C—C6C—C5C120.1 (5)
C2A—C1A—C6A118.1 (4)C1C—C6C—H6C127 (3)
C2A—C1A—I1A123.8 (3)C5C—C6C—H6C112 (3)
C6A—C1A—I1A118.0 (3)C8C—C7C—C12C116.6 (5)
C3A—C2A—C1A118.6 (4)C8C—C7C—C1C122.0 (4)
C3A—C2A—I2A118.3 (3)C12C—C7C—C1C121.3 (4)
C1A—C2A—I2A123.0 (3)C7C—C8C—C9C119.0 (5)
F1A—C3A—C4A117.7 (4)C7C—C8C—H8C119 (3)
F1A—C3A—C2A120.4 (4)C9C—C8C—H8C122 (3)
C4A—C3A—C2A121.9 (5)N10C—C9C—C8C124.1 (5)
C4A—C3A—I2A159.6 (4)N10C—C9C—H9C119 (3)
F2A—C4A—C5A120.6 (5)C8C—C9C—H9C116 (3)
F2A—C4A—C3A120.1 (5)C11C—N10C—C9C116.0 (5)
C5A—C4A—C3A119.2 (5)C11C—N10C—I2Aiii108.5 (4)
F3A—C5A—C4A119.7 (5)C9C—N10C—I2Aiii132.1 (4)
F3A—C5A—C6A120.0 (5)N10C—C11C—C12C125.4 (6)
C4A—C5A—C6A120.2 (4)N10C—C11C—H11C119 (3)
F4A—C6A—C5A118.1 (4)C12C—C11C—H11C115 (3)
F4A—C6A—C1A120.2 (4)C7C—C12C—C11C118.8 (5)
C5A—C6A—C1A121.7 (4)C7C—C12C—H12C116 (3)
C5A—C6A—I1A159.6 (4)C11C—C12C—H12C125 (3)
C1B—I1B—N4D172.45 (17)C12D—C7D—C8D114.9 (5)
N4D—I1B—C6B162.51 (16)C12D—C7D—C1D122.9 (5)
C2B—I2B—N10Dii176.19 (17)C8D—C7D—C1D122.1 (4)
N10Dii—I2B—C3B159.58 (14)C7D—C12D—C11D120.4 (5)
C6B—C1B—C2B119.3 (4)C7D—C12D—H12D108 (3)
C6B—C1B—I1B118.4 (4)C11D—C12D—H12D132 (3)
C2B—C1B—I1B122.3 (4)N10D—C11D—C12D124.8 (6)
C3B—C2B—C1B118.6 (5)N10D—C11D—H11D125 (3)
C3B—C2B—I2B117.4 (4)C12D—C11D—H11D110 (3)
C1B—C2B—I2B124.0 (3)C11D—N10D—C9D116.3 (5)
F1B—C3B—C4B117.4 (5)C11D—N10D—I2Biv117.4 (4)
F1B—C3B—C2B121.6 (5)C9D—N10D—I2Biv121.5 (4)
C4B—C3B—C2B121.0 (5)N10D—C9D—C8D123.4 (6)
C4B—C3B—I2B159.4 (4)N10D—C9D—H9D126 (3)
C5B—C4B—F2B120.6 (6)C8D—C9D—H9D110 (3)
C5B—C4B—C3B119.7 (5)C7D—C8D—C9D120.1 (5)
F2B—C4B—C3B119.6 (6)C7D—C8D—H8D110 (3)
C4B—C5B—F3B119.7 (6)C9D—C8D—H8D130 (3)
C4B—C5B—C6B120.3 (5)C6D—C1D—C2D115.3 (5)
F3B—C5B—C6B120.0 (6)C6D—C1D—C7D122.1 (5)
F4B—C6B—C5B117.8 (5)C2D—C1D—C7D122.6 (5)
F4B—C6B—C1B121.2 (5)C1D—C2D—C3D119.1 (6)
C5B—C6B—C1B120.9 (5)C1D—C2D—H2D114 (4)
C5B—C6B—I1B158.7 (4)C3D—C2D—H2D126 (4)
C6C—C1C—C2C116.2 (4)N4D—C3D—C2D124.7 (6)
C6C—C1C—C7C121.3 (4)N4D—C3D—H3D121 (3)
C2C—C1C—C7C122.4 (4)C2D—C3D—H3D114 (3)
C1C—C2C—C3C119.6 (5)C3D—N4D—C5D115.8 (5)
C1C—C2C—H2C119 (3)C3D—N4D—I1B118.5 (4)
C3C—C2C—H2C120 (3)C5D—N4D—I1B119.9 (4)
N4C—C3C—C2C124.1 (6)N4D—C5D—C6D123.4 (6)
N4C—C3C—H3C117 (3)N4D—C5D—H5D110 (3)
C2C—C3C—H3C119 (3)C6D—C5D—H5D126 (3)
C3C—N4C—C5C116.3 (5)C5D—C6D—C1D121.6 (6)
C3C—N4C—I1A111.3 (4)C5D—C6D—H6D116 (3)
C5C—N4C—I1A127.2 (4)C1D—C6D—H6D123 (3)
N4C—C5C—C6C123.6 (5)
C6A—C1A—C2A—C3A2.3 (6)F3B—C5B—C6B—C1B178.7 (4)
I1A—C1A—C2A—C3A177.7 (3)C4B—C5B—C6B—I1B3.0 (14)
C6A—C1A—C2A—I2A175.9 (3)F3B—C5B—C6B—I1B175.0 (7)
I1A—C1A—C2A—I2A4.1 (5)C2B—C1B—C6B—F4B179.9 (4)
C1A—C2A—C3A—F1A177.9 (4)I1B—C1B—C6B—F4B0.4 (6)
I2A—C2A—C3A—F1A3.8 (6)C2B—C1B—C6B—C5B2.5 (7)
C1A—C2A—C3A—C4A1.2 (7)I1B—C1B—C6B—C5B177.8 (4)
I2A—C2A—C3A—C4A177.0 (4)C2B—C1B—C6B—I1B179.7 (6)
C1A—C2A—C3A—I2A178.3 (6)C6C—C1C—C2C—C3C0.8 (8)
F1A—C3A—C4A—F2A0.5 (7)C7C—C1C—C2C—C3C179.9 (5)
C2A—C3A—C4A—F2A179.7 (4)C1C—C2C—C3C—N4C1.8 (10)
I2A—C3A—C4A—F2A175.1 (7)C2C—C3C—N4C—C5C1.7 (9)
F1A—C3A—C4A—C5A179.7 (5)C3C—N4C—C5C—C6C0.7 (9)
C2A—C3A—C4A—C5A0.6 (8)C2C—C1C—C6C—C5C0.2 (8)
I2A—C3A—C4A—C5A4.7 (14)C7C—C1C—C6C—C5C178.9 (5)
F2A—C4A—C5A—F3A1.5 (8)N4C—C5C—C6C—C1C0.3 (9)
C3A—C4A—C5A—F3A178.3 (4)C6C—C1C—C7C—C8C165.7 (5)
F2A—C4A—C5A—C6A179.0 (4)C2C—C1C—C7C—C8C13.3 (7)
C3A—C4A—C5A—C6A1.2 (8)C6C—C1C—C7C—C12C14.7 (7)
F3A—C5A—C6A—F4A0.4 (7)C2C—C1C—C7C—C12C166.3 (5)
C4A—C5A—C6A—F4A179.9 (4)C12C—C7C—C8C—C9C0.1 (8)
F3A—C5A—C6A—C1A179.5 (4)C1C—C7C—C8C—C9C179.5 (5)
C4A—C5A—C6A—C1A0.0 (8)C7C—C8C—C9C—N10C0.6 (9)
F3A—C5A—C6A—I1A177.5 (7)C8C—C9C—N10C—C11C0.7 (9)
C4A—C5A—C6A—I1A3.0 (13)C9C—N10C—C11C—C12C0.4 (10)
C2A—C1A—C6A—F4A178.1 (4)C8C—C7C—C12C—C11C0.2 (8)
I1A—C1A—C6A—F4A1.9 (6)C1C—C7C—C12C—C11C179.8 (5)
C2A—C1A—C6A—C5A1.7 (7)N10C—C11C—C12C—C7C0.1 (10)
I1A—C1A—C6A—C5A178.3 (4)C8D—C7D—C12D—C11D0.6 (8)
C2A—C1A—C6A—I1A180.0 (6)C1D—C7D—C12D—C11D179.9 (6)
C6B—C1B—C2B—C3B3.5 (7)C7D—C12D—C11D—N10D0.8 (11)
I1B—C1B—C2B—C3B176.9 (3)C12D—C11D—N10D—C9D0.7 (11)
C6B—C1B—C2B—I2B176.0 (3)C12D—C11D—N10D—I2Biv155.0 (6)
I1B—C1B—C2B—I2B3.7 (5)C11D—N10D—C9D—C8D0.9 (12)
C1B—C2B—C3B—F1B179.4 (4)I2Biv—N10D—C9D—C8D155.5 (6)
I2B—C2B—C3B—F1B1.1 (6)C12D—C7D—C8D—C9D2.0 (9)
C1B—C2B—C3B—C4B1.4 (7)C1D—C7D—C8D—C9D178.7 (6)
I2B—C2B—C3B—C4B178.1 (4)N10D—C9D—C8D—C7D2.3 (13)
C1B—C2B—C3B—I2B179.5 (6)C12D—C7D—C1D—C6D8.7 (8)
F1B—C3B—C4B—C5B177.5 (5)C8D—C7D—C1D—C6D170.6 (6)
C2B—C3B—C4B—C5B1.7 (8)C12D—C7D—C1D—C2D169.3 (6)
I2B—C3B—C4B—C5B1.7 (14)C8D—C7D—C1D—C2D11.4 (8)
F1B—C3B—C4B—F2B1.6 (7)C6D—C1D—C2D—C3D1.4 (9)
C2B—C3B—C4B—F2B179.2 (4)C7D—C1D—C2D—C3D179.6 (6)
I2B—C3B—C4B—F2B177.4 (7)C1D—C2D—C3D—N4D0.6 (12)
F2B—C4B—C5B—F3B0.1 (8)C2D—C3D—N4D—C5D0.6 (11)
C3B—C4B—C5B—F3B179.2 (4)C3D—N4D—C5D—C6D1.0 (10)
F2B—C4B—C5B—C6B178.2 (5)I1B—N4D—C5D—C6D151.9 (6)
C3B—C4B—C5B—C6B2.8 (9)N4D—C5D—C6D—C1D0.2 (11)
C4B—C5B—C6B—F4B176.8 (5)C2D—C1D—C6D—C5D1.1 (9)
F3B—C5B—C6B—F4B1.2 (7)C7D—C1D—C6D—C5D179.3 (6)
C4B—C5B—C6B—C1B0.7 (8)
Symmetry codes: (i) x, y1/2, z1/2; (ii) x1/2, y+1, z; (iii) x, y1/2, z+1/2; (iv) x+1/2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2C—H2C···F1Bv0.94 (2)2.54 (4)3.452 (7)165 (4)
C5C—H5C···F3Avi0.92 (2)2.68 (3)3.557 (7)160 (3)
C6C—H6C···F4Bvii0.93 (2)2.44 (4)3.342 (7)165 (3)
C2D—H2D···F1Aviii0.93 (2)2.69 (4)3.597 (7)167 (3)
C6D—H6D···F4Aix0.92 (2)2.46 (4)3.313 (7)154 (3)
Symmetry codes: (v) x+1/2, y, z; (vi) x, y, z; (vii) x1/2, y, z; (viii) x+1/2, y+1/2, z1/2; (ix) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC10H8N2·C6F4I2
Mr558.04
Crystal system, space groupMonoclinic, I2/a
Temperature (K)290
a, b, c (Å)14.2535 (10), 33.714 (3), 14.3511 (12)
β (°) 100.831 (6)
V3)6773.5 (10)
Z16
Radiation typeMo Kα
µ (mm1)3.75
Crystal size (mm)0.40 × 0.16 × 0.11
Data collection
DiffractometerBruker SMART-APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.668, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
15718, 7796, 5552
Rint0.018
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.094, 0.97
No. of reflections7796
No. of parameters498
No. of restraints148
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.66, 0.60

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett and Johnson, 1996), SHELXL97 and PARST (Nardelli, 1983).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2C—H2C···F1Bi0.94 (2)2.54 (4)3.452 (7)165 (4)
C5C—H5C···F3Aii0.92 (2)2.68 (3)3.557 (7)160 (3)
C6C—H6C···F4Biii0.93 (2)2.44 (4)3.342 (7)165 (3)
C2D—H2D···F1Aiv0.93 (2)2.69 (4)3.597 (7)167 (3)
C6D—H6D···F4Av0.92 (2)2.46 (4)3.313 (7)154 (3)
Symmetry codes: (i) x+1/2, y, z; (ii) x, y, z; (iii) x1/2, y, z; (iv) x+1/2, y+1/2, z1/2; (v) x+1/2, y+1/2, z+1/2.
 

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