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O intermolecular bond connecting the bpNO and F4dIb molecules into one-dimensional infinite chains, as well as the other non-covalent interactions present in the crystal, such as C—HO, C—HF and C—HI hydrogen bonds and CC, CN, CI and FF interactions, have been investigated. The integration of electron density over the atomic basins reveals the electrostatic nature of the IO halogen bond, which is very similar to a previously analysed IN halogen bond.Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768104014557/bs5005sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S0108768104014557/bs5005sup2.hkl |
 | Portable Document Format (PDF) file https://doi.org/10.1107/S0108768104014557/bs5005sup3.pdf |
CCDC reference: 255089
Data collection: Bruker SMART; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SIR92, (Altomare et al., 1994); program(s) used to refine structure: VALRAY (Stewart & Spackman, 1983; Stewart, Spackman & Flensburg, 2001); molecular graphics: ORTEP III ( Burnett&Johnson, 1996); software used to prepare material for publication: PARST (Nardelli, 1995).
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![[Figure 6]](http://journals.iucr.org/b/issues/2004/05/00/bs5005/bs5005fig6thm.gif)
| (C10H8N2O2)·(C6I2F4) | Z = 1 |
| Mr = 590.04 | F(000) = 276 |
| Triclinic, P1 | Dx = 2.274 Mg m−3 |
| a = 4.2279 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 8.009 (2) Å | Cell parameters from 8425 reflections |
| c = 13.569 (3) Å | θ = 2.8–59.5° |
| α = 101.180 (5)° | µ = 3.70 mm−1 |
| β = 98.946 (5)° | T = 90 K |
| γ = 102.349 (5)° | Prism, colourless |
| V = 430.91 (18) Å3 | 0.30 × 0.11 × 0.04 mm |
| Bruker APEX CCD area detector diffractometer | 12612 independent reflections |
| Radiation source: fine-focus sealed tube | 12122 reflections with > 0 |
| Graphite monochromator | Rint = 0.027 |
| ω and ϕ scans | θmax = 60.1°, θmin = 2.7° |
| Absorption correction: multi-scan SADABS, Bruker, 1997 | h = −8→9 |
| Tmin = 0.819, Tmax = 1.000 | k = −19→19 |
| 53777 measured reflections | l = −33→32 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.050 | All H-atom parameters refined |
| S = 1.01 | w = 1/[σ2(Fo2)] |
| 12579 reflections | (Δ/σ)max = 0.001 |
| 387 parameters | Δρmax = 0.22 e Å−3 |
| 0 restraints | Δρmin = −0.49 e Å−3 |
| Primary atom site location: structure-invariant direct methods |
| (C10H8N2O2)·(C6I2F4) | γ = 102.349 (5)° |
| Mr = 590.04 | V = 430.91 (18) Å3 |
| Triclinic, P1 | Z = 1 |
| a = 4.2279 (10) Å | Mo Kα radiation |
| b = 8.009 (2) Å | µ = 3.70 mm−1 |
| c = 13.569 (3) Å | T = 90 K |
| α = 101.180 (5)° | 0.30 × 0.11 × 0.04 mm |
| β = 98.946 (5)° |
| Bruker APEX CCD area detector diffractometer | 12612 independent reflections |
| Absorption correction: multi-scan SADABS, Bruker, 1997 | 12122 reflections with > 0 |
| Tmin = 0.819, Tmax = 1.000 | Rint = 0.027 |
| 53777 measured reflections |
| wR(F2) = 0.050 | 0 restraints |
| S = 1.01 | All H-atom parameters refined |
| 12579 reflections | Δρmax = 0.22 e Å−3 |
| 387 parameters | Δρmin = −0.49 e Å−3 |
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 > 0 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. |
| x | y | z | Uiso*/Ueq | ||
| I | 0.61751 (7) | 0.30261 (5) | 0.19332 (2) | 0.01490 (6) | |
| C6 | 0.2567 (2) | 0.12134 (13) | 0.07682 (7) | 0.01395 (16) | |
| C7 | 0.1769 (3) | 0.15072 (15) | −0.02026 (8) | 0.01618 (19) | |
| C8 | −0.0747 (3) | 0.03179 (14) | −0.09519 (7) | 0.01561 (18) | |
| F1 | 0.336 (2) | 0.2961 (10) | −0.0437 (5) | 0.0268 (4) | |
| F2 | −0.138 (2) | 0.0672 (10) | −0.1879 (4) | 0.0241 (3) | |
| O | 1.0343 (3) | 0.51013 (15) | 0.36844 (8) | 0.01676 (18) | |
| N | 1.2965 (2) | 0.64053 (11) | 0.40300 (7) | 0.01241 (14) | |
| C1 | 1.4311 (2) | 0.73095 (13) | 0.33832 (7) | 0.01401 (16) | |
| C2 | 1.7050 (2) | 0.87171 (13) | 0.37509 (7) | 0.01398 (16) | |
| C3 | 1.8552 (2) | 0.92422 (11) | 0.47969 (7) | 0.01168 (14) | |
| C4 | 1.7114 (2) | 0.82543 (12) | 0.54328 (7) | 0.01274 (15) | |
| C5 | 1.4344 (2) | 0.68731 (12) | 0.50483 (7) | 0.01327 (15) | |
| H1 | 1.300 (9) | 0.678 (5) | 0.256 (3) | 0.020 (9)* | |
| H2 | 1.795 (7) | 0.936 (4) | 0.322 (2) | 0.034 (9)* | |
| H4 | 1.782 (8) | 0.849 (4) | 0.626 (3) | 0.041 (10)* | |
| H5 | 1.305 (7) | 0.613 (4) | 0.550 (2) | 0.031 (10)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| I | 0.01292 (10) | 0.01735 (11) | 0.01443 (10) | 0.00143 (8) | 0.00086 (8) | −0.00107 (9) |
| C6 | 0.0148 (3) | 0.0154 (3) | 0.0116 (3) | 0.0016 (2) | 0.0012 (2) | 0.0014 (2) |
| C7 | 0.0198 (4) | 0.0165 (3) | 0.0123 (3) | −0.0013 (3) | 0.0007 (2) | 0.0031 (2) |
| C8 | 0.0191 (3) | 0.0167 (3) | 0.0110 (3) | 0.0007 (3) | 0.0004 (2) | 0.0029 (2) |
| F1 | 0.0370 (8) | 0.0227 (5) | 0.0207 (5) | −0.0093 (5) | 0.0004 (5) | 0.0079 (4) |
| F2 | 0.0340 (6) | 0.0249 (5) | 0.0136 (3) | −0.0016 (5) | −0.0029 (4) | 0.0068 (3) |
| O | 0.0166 (3) | 0.0175 (3) | 0.0162 (3) | −0.0052 (3) | −0.0008 (2) | 0.0023 (3) |
| N | 0.0123 (2) | 0.0123 (2) | 0.0127 (2) | −0.0003 (2) | 0.0005 (2) | 0.0021 (2) |
| C1 | 0.0145 (3) | 0.0158 (3) | 0.0117 (3) | −0.0013 (2) | −0.0005 (2) | 0.0028 (2) |
| C2 | 0.0147 (3) | 0.0152 (3) | 0.0120 (3) | −0.0009 (2) | 0.0009 (2) | 0.0032 (2) |
| C3 | 0.0110 (2) | 0.0118 (2) | 0.0123 (2) | 0.0006 (2) | 0.0011 (2) | 0.0023 (2) |
| C4 | 0.0132 (3) | 0.0131 (3) | 0.0119 (3) | −0.0009 (2) | 0.0003 (2) | 0.0025 (2) |
| C5 | 0.0135 (3) | 0.0136 (3) | 0.0127 (3) | −0.0006 (2) | 0.0015 (2) | 0.0032 (2) |
| I—C6 | 2.0848 (9) | C1—C2 | 1.3800 (12) |
| C6—C7 | 1.3858 (15) | C1—H1 | 1.12 (4) |
| C6—C8i | 1.3903 (15) | C2—C3 | 1.4031 (13) |
| C7—F1 | 1.336 (8) | C2—H2 | 1.03 (4) |
| C7—C8 | 1.3883 (13) | C3—C4 | 1.4007 (14) |
| C8—F2 | 1.342 (6) | C3—C3ii | 1.4737 (11) |
| C8—C6i | 1.390 (2) | C4—C5 | 1.3783 (12) |
| O—N | 1.3010 (12) | C4—H4 | 1.08 (3) |
| N—C1 | 1.3579 (15) | C5—H5 | 1.07 (4) |
| N—C5 | 1.3582 (13) | ||
| C7—C6—C8i | 117.05 (8) | C2—C1—H1 | 126 (2) |
| C7—C6—I | 122.06 (7) | C1—C2—C3 | 121.25 (9) |
| C8i—C6—I | 120.83 (7) | C1—C2—H2 | 117 (2) |
| F1—C7—C6 | 120.8 (3) | C3—C2—H2 | 121 (2) |
| F1—C7—C8 | 118.2 (4) | C4—C3—C2 | 116.09 (8) |
| C6—C7—C8 | 121.00 (10) | C4—C3—C3ii | 122.03 (9) |
| F2—C8—C7 | 118.1 (3) | C2—C3—C3ii | 121.87 (11) |
| F2—C8—C6i | 119.9 (3) | C5—C4—C3 | 121.47 (9) |
| C7—C8—C6i | 121.95 (9) | C5—C4—H4 | 111 (2) |
| O—N—C1 | 120.56 (10) | C3—C4—H4 | 127 (2) |
| O—N—C5 | 119.57 (9) | N—C5—C4 | 120.61 (9) |
| C1—N—C5 | 119.87 (9) | N—C5—H5 | 115 (2) |
| N—C1—C2 | 120.69 (10) | C4—C5—H5 | 125 (2) |
| N—C1—H1 | 113 (2) |
| Symmetry codes: (i) −x, −y, −z; (ii) −x+4, −y+2, −z+1. |
Experimental details
| Crystal data | |
| Chemical formula | (C10H8N2O2)·(C6I2F4) |
| Mr | 590.04 |
| Crystal system, space group | Triclinic, P1 |
| Temperature (K) | 90 |
| a, b, c (Å) | 4.2279 (10), 8.009 (2), 13.569 (3) |
| α, β, γ (°) | 101.180 (5), 98.946 (5), 102.349 (5) |
| V (Å3) | 430.91 (18) |
| Z | 1 |
| Radiation type | Mo Kα |
| µ (mm−1) | 3.70 |
| Crystal size (mm) | 0.30 × 0.11 × 0.04 |
| Data collection | |
| Diffractometer | Bruker APEX CCD area detector diffractometer |
| Absorption correction | Multi-scan SADABS, Bruker, 1997 |
| Tmin, Tmax | 0.819, 1.000 |
| No. of measured, independent and observed ( > 0) reflections | 53777, 12612, 12122 |
| Rint | 0.027 |
| (sin θ/λ)max (Å−1) | 1.220 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | ?, 0.050, 1.01 |
| No. of reflections | 12579 |
| No. of parameters | 387 |
| H-atom treatment | All H-atom parameters refined |
| Δρmax, Δρmin (e Å−3) | 0.22, −0.49 |
Computer programs: Bruker SMART, Bruker SAINT, SIR92, (Altomare et al., 1994), VALRAY (Stewart & Spackman, 1983; Stewart, Spackman & Flensburg, 2001), ORTEP III ( Burnett&Johnson, 1996), PARST (Nardelli, 1995).
