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access(E)-1-(2-Iodophenyl)-2-phenyldiazene
ainGAP Centre for Research Based Innovation, Center for Materials Science and Nanotechnology, Department of Chemistry, University of Oslo, PO Box 1033 Blindern, Oslo 0315, Norway, and bDepartment of Chemistry, University of Oslo, PO Box 1033 Blindern, Oslo 0315, Norway
*Correspondence e-mail: david.wragg@smn.uio.no
The molecule of the title compound, C12H9IN2, is approximately planar [maximum deviation = 0.020 (5) Å] with a trans arrangement of the groups around the N=N double bond. This double bond is rotated away from the iodine substiuent.
![[Scheme 1]](qm2021scheme1.gif)
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2011![[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]](../../../../../../logos/arrows/e_arr.gif "Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.")
); cell SAINT (Bruker, 2011); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) in WinGX (Farrugia, 1999); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supporting information
contains datablocks I, global. DOI: 10.1107/S1600536811032119/qm2021sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536811032119/qm2021Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811032119/qm2021Isup3.cml
(1) was synthesized according to the literature procedure (Badger et al. 1964) and recrystallized from absolute ethanol in the form of long orange needles.
Least squares was carried out with SHELXL97 (Sheldrick, 2008) as implemented in WinGX (Farrugia, 1999). Hydrogen atoms were refined using a riding model the Uiso set to 1.2 times that of the heavy atom to which they are attached.
Data collection: APEX2 (Bruker, 2011); cell SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) in WinGX (Farrugia, 1999); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).
![[Figure 1]](./qm2021fig1thm.gif) | Fig. 1. The asymmetric unit of (1) shown with thermal ellipsoids at 50% probability. Hydrogen atoms unlabelled for clarity. |
![[Figure 2]](./qm2021fig2thm.gif) | Fig. 2. Packing diagram of (1) viewed along the a-axis. |
![[Figure 3]](./qm2021fig3thm.gif) | Fig. 3. Packing diagram of (1) viewed along the c-axis. |
| C12H9IN2 | F(000) = 592 |
| Mr = 308.11 | Dx = 1.886 Mg m−3 |
| Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 4258 reflections |
| a = 4.628 (3) Å | θ = 2.2–25.0° |
| b = 12.801 (9) Å | µ = 2.92 mm−1 |
| c = 18.312 (12) Å | T = 296 K |
| V = 1084.9 (13) Å3 | Needle, orange |
| Z = 4 | 1.00 × 0.07 × 0.07 mm |
| Bruker APEXII CCD diffractometer | 1930 independent reflections |
| Radiation source: sealed tube | 1842 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.033 |
| ϕ and ω scans | θmax = 25.1°, θmin = 1.9° |
| Absorption correction: multi-scan (SADABS; Bruker, 2011) | h = −5→5 |
| Tmin = 0.783, Tmax = 0.822 | k = −15→15 |
| 10050 measured reflections | l = −21→21 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
| wR(F2) = 0.070 | w = 1/[σ2(Fo2) + (0.0345P)2 + 0.6387P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max = 0.001 |
| 1930 reflections | Δρmax = 0.57 e Å−3 |
| 137 parameters | Δρmin = −0.48 e Å−3 |
| 0 restraints | Absolute structure: Flack (1983), 763 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.08 (4) |
| C12H9IN2 | V = 1084.9 (13) Å3 |
| Mr = 308.11 | Z = 4 |
| Orthorhombic, P212121 | Mo Kα radiation |
| a = 4.628 (3) Å | µ = 2.92 mm−1 |
| b = 12.801 (9) Å | T = 296 K |
| c = 18.312 (12) Å | 1.00 × 0.07 × 0.07 mm |
| Bruker APEXII CCD diffractometer | 1930 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2011) | 1842 reflections with I > 2σ(I) |
| Tmin = 0.783, Tmax = 0.822 | Rint = 0.033 |
| 10050 measured reflections |
| R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
| wR(F2) = 0.070 | Δρmax = 0.57 e Å−3 |
| S = 1.07 | Δρmin = −0.48 e Å−3 |
| 1930 reflections | Absolute structure: Flack (1983), 763 Friedel pairs |
| 137 parameters | Absolute structure parameter: 0.08 (4) |
| 0 restraints |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. |
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.1092 (10) | 0.3166 (4) | 0.1768 (3) | 0.0549 (12) | |
| H1 | −0.0297 | 0.3672 | 0.1865 | 0.066* | |
| C2 | 0.1881 (10) | 0.2473 (3) | 0.2300 (3) | 0.0521 (11) | |
| H2 | 0.1032 | 0.2496 | 0.2760 | 0.062* | |
| C3 | 0.3968 (9) | 0.1737 (3) | 0.2138 (2) | 0.0450 (10) | |
| C4 | 0.5235 (10) | 0.1691 (3) | 0.1465 (2) | 0.0389 (8) | |
| C5 | 1.0496 (8) | 0.0040 (3) | 0.0680 (2) | 0.0407 (9) | |
| C6 | 1.1155 (10) | −0.0629 (3) | 0.1240 (3) | 0.0530 (10) | |
| H6 | 1.0261 | −0.0561 | 0.1693 | 0.064* | |
| C7 | 1.3160 (11) | −0.1401 (4) | 0.1121 (3) | 0.0643 (13) | |
| H7 | 1.3637 | −0.1860 | 0.1495 | 0.077* | |
| C8 | 1.4446 (10) | −0.1497 (4) | 0.0459 (3) | 0.0637 (14) | |
| H8 | 1.5794 | −0.2025 | 0.0383 | 0.076* | |
| C9 | 0.2346 (10) | 0.3116 (3) | 0.1090 (3) | 0.0523 (11) | |
| H9 | 0.1763 | 0.3584 | 0.0731 | 0.063* | |
| C10 | 0.4372 (8) | 0.2417 (3) | 0.0934 (2) | 0.0420 (10) | |
| H10 | 0.5218 | 0.2408 | 0.0473 | 0.050* | |
| C11 | 1.1796 (10) | −0.0058 (4) | 0.0017 (3) | 0.0550 (12) | |
| H11 | 1.1331 | 0.0400 | −0.0360 | 0.066* | |
| C12 | 1.3793 (10) | −0.0833 (4) | −0.0095 (3) | 0.0638 (14) | |
| H12 | 1.4693 | −0.0903 | −0.0546 | 0.077* | |
| N1 | 0.8420 (7) | 0.0855 (3) | 0.07490 (19) | 0.0433 (8) | |
| N2 | 0.7314 (7) | 0.0892 (3) | 0.13658 (19) | 0.0422 (8) | |
| I1 | 0.51175 (8) | 0.06841 (2) | 0.294862 (15) | 0.06222 (13) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.050 (2) | 0.039 (2) | 0.075 (3) | 0.0054 (19) | 0.000 (2) | −0.010 (2) |
| C2 | 0.048 (3) | 0.052 (3) | 0.056 (3) | −0.006 (2) | 0.009 (2) | −0.013 (2) |
| C3 | 0.045 (2) | 0.042 (2) | 0.048 (2) | −0.0057 (17) | −0.0028 (18) | −0.0042 (18) |
| C4 | 0.036 (2) | 0.0332 (16) | 0.0476 (19) | 0.003 (2) | 0.000 (2) | −0.0029 (13) |
| C5 | 0.032 (2) | 0.039 (2) | 0.051 (2) | 0.0013 (18) | −0.0029 (18) | −0.0058 (15) |
| C6 | 0.051 (2) | 0.050 (2) | 0.058 (3) | 0.005 (2) | 0.001 (2) | 0.002 (2) |
| C7 | 0.056 (3) | 0.051 (3) | 0.086 (4) | 0.011 (2) | −0.006 (3) | 0.006 (3) |
| C8 | 0.043 (3) | 0.048 (2) | 0.100 (4) | 0.008 (2) | −0.007 (3) | −0.021 (2) |
| C9 | 0.055 (3) | 0.042 (2) | 0.060 (3) | −0.002 (2) | −0.013 (2) | 0.003 (2) |
| C10 | 0.038 (2) | 0.047 (2) | 0.041 (2) | −0.0067 (18) | −0.0007 (17) | −0.0027 (16) |
| C11 | 0.054 (3) | 0.063 (3) | 0.049 (3) | 0.004 (2) | −0.001 (2) | −0.005 (2) |
| C12 | 0.046 (2) | 0.079 (4) | 0.066 (3) | 0.005 (3) | 0.003 (2) | −0.025 (3) |
| N1 | 0.0426 (18) | 0.040 (2) | 0.047 (2) | 0.0022 (16) | 0.0011 (16) | −0.0016 (15) |
| N2 | 0.0394 (17) | 0.044 (2) | 0.0433 (19) | −0.0003 (15) | 0.0006 (15) | −0.0031 (15) |
| I1 | 0.0674 (2) | 0.0688 (2) | 0.05044 (18) | −0.0007 (2) | 0.0006 (2) | 0.01231 (12) |
| C1—C2 | 1.367 (7) | C6—H6 | 0.9300 |
| C1—C9 | 1.371 (7) | C7—C8 | 1.356 (7) |
| C1—H1 | 0.9300 | C7—H7 | 0.9300 |
| C2—C3 | 1.381 (6) | C8—C12 | 1.357 (7) |
| C2—H2 | 0.9300 | C8—H8 | 0.9300 |
| C3—C4 | 1.367 (6) | C9—C10 | 1.328 (6) |
| C3—I1 | 2.075 (4) | C9—H9 | 0.9300 |
| C4—C10 | 1.403 (5) | C10—H10 | 0.9300 |
| C4—N2 | 1.416 (5) | C11—C12 | 1.371 (7) |
| C5—C11 | 1.361 (6) | C11—H11 | 0.9300 |
| C5—C6 | 1.370 (6) | C12—H12 | 0.9300 |
| C5—N1 | 1.424 (5) | N1—N2 | 1.241 (5) |
| C6—C7 | 1.374 (6) | ||
| C2—C1—C9 | 120.1 (4) | C8—C7—H7 | 119.9 |
| C2—C1—H1 | 120.0 | C6—C7—H7 | 119.9 |
| C9—C1—H1 | 120.0 | C7—C8—C12 | 120.9 (4) |
| C1—C2—C3 | 118.5 (4) | C7—C8—H8 | 119.5 |
| C1—C2—H2 | 120.8 | C12—C8—H8 | 119.5 |
| C3—C2—H2 | 120.8 | C10—C9—C1 | 121.7 (4) |
| C4—C3—C2 | 121.5 (4) | C10—C9—H9 | 119.1 |
| C4—C3—I1 | 120.5 (3) | C1—C9—H9 | 119.1 |
| C2—C3—I1 | 118.0 (3) | C9—C10—C4 | 119.9 (4) |
| C3—C4—C10 | 118.3 (4) | C9—C10—H10 | 120.1 |
| C3—C4—N2 | 116.0 (3) | C4—C10—H10 | 120.1 |
| C10—C4—N2 | 125.7 (4) | C5—C11—C12 | 119.8 (5) |
| C11—C5—C6 | 120.8 (4) | C5—C11—H11 | 120.1 |
| C11—C5—N1 | 116.4 (4) | C12—C11—H11 | 120.1 |
| C6—C5—N1 | 122.8 (4) | C8—C12—C11 | 119.5 (5) |
| C5—C6—C7 | 118.7 (5) | C8—C12—H12 | 120.3 |
| C5—C6—H6 | 120.6 | C11—C12—H12 | 120.3 |
| C7—C6—H6 | 120.6 | N2—N1—C5 | 112.8 (3) |
| C8—C7—C6 | 120.3 (5) | N1—N2—C4 | 115.1 (3) |
| C9—C1—C2—C3 | 0.6 (7) | C1—C9—C10—C4 | 1.3 (7) |
| C1—C2—C3—C4 | −0.1 (6) | C3—C4—C10—C9 | −0.8 (6) |
| C1—C2—C3—I1 | −179.5 (3) | N2—C4—C10—C9 | 178.5 (4) |
| C2—C3—C4—C10 | 0.3 (6) | C6—C5—C11—C12 | −0.1 (7) |
| I1—C3—C4—C10 | 179.6 (3) | N1—C5—C11—C12 | −179.2 (4) |
| C2—C3—C4—N2 | −179.1 (4) | C7—C8—C12—C11 | −0.3 (8) |
| I1—C3—C4—N2 | 0.2 (5) | C5—C11—C12—C8 | 0.1 (7) |
| C11—C5—C6—C7 | 0.1 (7) | C11—C5—N1—N2 | 179.6 (4) |
| N1—C5—C6—C7 | 179.1 (4) | C6—C5—N1—N2 | 0.5 (5) |
| C5—C6—C7—C8 | −0.2 (7) | C5—N1—N2—C4 | 179.9 (3) |
| C6—C7—C8—C12 | 0.3 (8) | C3—C4—N2—N1 | 179.3 (4) |
| C2—C1—C9—C10 | −1.2 (7) | C10—C4—N2—N1 | 0.0 (6) |
Experimental details
| Crystal data | |
| Chemical formula | C12H9IN2 |
| Mr | 308.11 |
| Crystal system, space group | Orthorhombic, P212121 |
| Temperature (K) | 296 |
| a, b, c (Å) | 4.628 (3), 12.801 (9), 18.312 (12) |
| V (Å3) | 1084.9 (13) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 2.92 |
| Crystal size (mm) | 1.00 × 0.07 × 0.07 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD diffractometer |
| Absorption correction | Multi-scan (SADABS; Bruker, 2011) |
| Tmin, Tmax | 0.783, 0.822 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 10050, 1930, 1842 |
| Rint | 0.033 |
| (sin θ/λ)max (Å−1) | 0.596 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.070, 1.07 |
| No. of reflections | 1930 |
| No. of parameters | 137 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.57, −0.48 |
| Absolute structure | Flack (1983), 763 Friedel pairs |
| Absolute structure parameter | 0.08 (4) |
Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) in WinGX (Farrugia, 1999), DIAMOND (Brandenburg, 2006), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Acknowledgements
The Norwegian research council is acknowledged for funding under RENERGI project No. 200014.
References
Badger, G. M., Drewer, R. J. & Lewis, G. E. (1964). Aust. J. Chem. 17, 1036–1049. CrossRef CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
(E)-1-(2-iodophenyl)-2-phenyldiazene (1) was synthesized by a literature procedure (Badger et al. 1964) and recrystallized from absolute ethanol. The molecule is planar with a trans arrangement of the phenyl groups around the N—N double bond. This double bond is rotated away from the iodine substiuent on C3 (Fig. 1). There are no strong intermolecular interactions, although π-stacking interactions may exist between the phenyl rings and the N—N double bonds (Fig. 2, 3).