 | Acta Crystallographica Section E Acta Crystallographica Section E CRYSTALLOGRAPHIC COMMUNICATIONS |
journal menu
organic compounds
| CRYSTALLOGRAPHIC COMMUNICATIONS |
access2-(2-Iodophenyl)isoindoline-1,3-dione
aOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139 Samsun, Turkey, and bOndokuz Mayıs University, Arts and Sciences Faculty, Department of Chemistry, 55139 Samsun, Turkey
*Correspondence e-mail: gunesd@omu.edu.tr
In the title compound, C14H8INO2, the dihedral angle between the isoindole ring and the phenyl ring of the 1-iodobenzene group is 84.77 (15)°. There is a short intermolecular I⋯O contact of 3.068 (3) Å in the crystal.
Related literature
For the biological activity of phthalimides, see: Kerrigan et al. (2000![[Kerrigan, J. E., Walters, M. C., Forrester, K. J., Crowder, J. B. & Christopher, L. J. (2000). Bioorg. Med. Chem. Lett. 10, 27-30.]](../../../../../../logos/arrows/e_arr.gif "Kerrigan, J. E., Walters, M. C., Forrester, K. J., Crowder, J. B. & Christopher, L. J. (2000). Bioorg. Med. Chem. Lett. 10, 27-30.")
); Lima et al. (2002). For the crystal structures of phthalimide derivatives, see: Devarajegowda et al. (2010); Sakthivel et al. (2007a,b); Nagaraj et al. (2005).
![[Scheme 1]](lw2057scheme1.gif)
Experimental
Crystal data
|
Data collection: X-AREA (Stoe & Cie, 2002); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: WinGX (Farrugia, 1999) and SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: WinGX (Farrugia, 1999) and SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX and PLATON (Spek, 2009).
Supporting information
contains datablocks I, global. DOI: 10.1107/S1600536811006544/lw2057sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536811006544/lw2057Isup2.hkl
The compound N-2-Iodophenylphthalimide was prepared by refluxing a mixture of a solution containing N-hydroxyphthalimide (0.0113 g 0.069 mmol) in 20 ml ethanol and a solution containing 4-amino-4-methylphenol (0.0303 g 0.069 mmol) in 20 ml ethanol. The reaction mixture was stirred for 1h under reflux. The crystals of N-2-Iodophenylphthalimide suitable for X-ray analysis were obtained from ethyl alcohol by slow evaporation (yield % 41; m.p 180.3–184.0 oC).
All hydrogen atoms were positioned geometrically (C—H=0.93 Å) and treated as riding with Uiso(H)=1.1Ueq(C).
Data collection: X-AREA (Stoe & Cie, 2002); cell X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: WinGX (Farrugia, 1999) and SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: WinGX (Farrugia, 1999) and SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
![[Figure 1]](./lw2057fig1thm.gif) | Fig. 1. The asymmetric unit of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./lw2057fig2thm.gif) | Fig. 2. The crystal packing of the title compound in the unit cell. |
| C14H8INO2 | F(000) = 672 |
| Mr = 349.11 | Dx = 1.812 Mg m−3 |
| Monoclinic, P21/c | Melting point: 455 K |
| Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
| a = 11.5318 (5) Å | Cell parameters from 26549 reflections |
| b = 8.0597 (2) Å | θ = 1.8–28.0° |
| c = 15.6134 (7) Å | µ = 2.50 mm−1 |
| β = 118.157 (3)° | T = 296 K |
| V = 1279.42 (9) Å3 | Prism, red |
| Z = 4 | 0.69 × 0.51 × 0.28 mm |
| Stoe IPDS 2 diffractometer | 2517 independent reflections |
| Radiation source: fine-focus sealed tube | 2434 reflections with I > 2σ(I) |
| Plane graphite monochromator | Rint = 0.033 |
| rotation method scans | θmax = 26.0°, θmin = 2.0° |
| Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | h = −14→14 |
| Tmin = 0.291, Tmax = 0.590 | k = −9→9 |
| 13075 measured reflections | l = −19→19 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.078 | H-atom parameters constrained |
| S = 1.11 | w = 1/[σ2(Fo2) + (0.0373P)2 + 1.3378P] where P = (Fo2 + 2Fc2)/3 |
| 2517 reflections | (Δ/σ)max = 0.002 |
| 163 parameters | Δρmax = 0.82 e Å−3 |
| 0 restraints | Δρmin = −1.05 e Å−3 |
| C14H8INO2 | V = 1279.42 (9) Å3 |
| Mr = 349.11 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 11.5318 (5) Å | µ = 2.50 mm−1 |
| b = 8.0597 (2) Å | T = 296 K |
| c = 15.6134 (7) Å | 0.69 × 0.51 × 0.28 mm |
| β = 118.157 (3)° |
| Stoe IPDS 2 diffractometer | 2517 independent reflections |
| Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2434 reflections with I > 2σ(I) |
| Tmin = 0.291, Tmax = 0.590 | Rint = 0.033 |
| 13075 measured reflections |
| R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
| wR(F2) = 0.078 | H-atom parameters constrained |
| S = 1.11 | Δρmax = 0.82 e Å−3 |
| 2517 reflections | Δρmin = −1.05 e Å−3 |
| 163 parameters |
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. |
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.6644 (3) | 0.2407 (4) | 0.1170 (2) | 0.0391 (6) | |
| C2 | 0.6487 (3) | 0.3409 (4) | 0.1906 (2) | 0.0388 (6) | |
| C3 | 0.5850 (3) | 0.4891 (4) | 0.1819 (2) | 0.0500 (7) | |
| H3 | 0.5418 | 0.5438 | 0.1225 | 0.060* | |
| C4 | 0.5880 (4) | 0.5537 (5) | 0.2652 (3) | 0.0581 (8) | |
| H4 | 0.5485 | 0.6557 | 0.2622 | 0.070* | |
| C5 | 0.6482 (4) | 0.4699 (5) | 0.3524 (3) | 0.0588 (9) | |
| H5 | 0.6469 | 0.5156 | 0.4066 | 0.071* | |
| C6 | 0.7105 (4) | 0.3194 (4) | 0.3610 (2) | 0.0535 (8) | |
| H6 | 0.7506 | 0.2624 | 0.4197 | 0.064* | |
| C7 | 0.7105 (3) | 0.2578 (4) | 0.2786 (2) | 0.0405 (6) | |
| C8 | 0.7669 (3) | 0.1017 (4) | 0.2642 (2) | 0.0445 (6) | |
| C9 | 0.7720 (3) | −0.0319 (3) | 0.12144 (19) | 0.0392 (6) | |
| C10 | 0.8848 (3) | −0.0215 (4) | 0.1120 (2) | 0.0425 (6) | |
| C11 | 0.9183 (4) | −0.1504 (5) | 0.0691 (2) | 0.0540 (8) | |
| H11 | 0.9939 | −0.1433 | 0.0621 | 0.065* | |
| C12 | 0.8393 (5) | −0.2892 (4) | 0.0369 (3) | 0.0630 (10) | |
| H12 | 0.8621 | −0.3762 | 0.0087 | 0.076* | |
| C13 | 0.7274 (5) | −0.2994 (4) | 0.0464 (3) | 0.0627 (10) | |
| H13 | 0.6744 | −0.3933 | 0.0243 | 0.075* | |
| C14 | 0.6924 (4) | −0.1705 (4) | 0.0887 (3) | 0.0527 (8) | |
| H14 | 0.6162 | −0.1774 | 0.0949 | 0.063* | |
| I1 | 1.00579 (2) | 0.18859 (3) | 0.158933 (17) | 0.06096 (11) | |
| N1 | 0.7345 (2) | 0.0987 (3) | 0.16550 (16) | 0.0399 (5) | |
| O1 | 0.6253 (2) | 0.2689 (3) | 0.03201 (15) | 0.0534 (5) | |
| O2 | 0.8266 (3) | −0.0042 (3) | 0.32190 (18) | 0.0722 (8) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0420 (14) | 0.0404 (14) | 0.0373 (14) | 0.0006 (12) | 0.0207 (12) | 0.0023 (12) |
| C2 | 0.0407 (14) | 0.0423 (14) | 0.0353 (13) | 0.0008 (11) | 0.0196 (12) | 0.0009 (11) |
| C3 | 0.0539 (17) | 0.0491 (17) | 0.0505 (16) | 0.0086 (14) | 0.0277 (14) | 0.0063 (14) |
| C4 | 0.060 (2) | 0.0550 (19) | 0.065 (2) | 0.0098 (16) | 0.0335 (17) | −0.0071 (16) |
| C5 | 0.0586 (19) | 0.071 (2) | 0.0498 (17) | 0.0052 (17) | 0.0283 (16) | −0.0170 (16) |
| C6 | 0.0536 (18) | 0.070 (2) | 0.0362 (15) | 0.0082 (15) | 0.0204 (14) | −0.0010 (14) |
| C7 | 0.0411 (14) | 0.0462 (15) | 0.0354 (13) | 0.0040 (12) | 0.0192 (12) | 0.0000 (12) |
| C8 | 0.0501 (16) | 0.0492 (17) | 0.0353 (13) | 0.0087 (13) | 0.0211 (12) | 0.0053 (12) |
| C9 | 0.0462 (15) | 0.0376 (14) | 0.0340 (13) | 0.0001 (11) | 0.0191 (12) | −0.0003 (11) |
| C10 | 0.0453 (15) | 0.0443 (15) | 0.0374 (14) | −0.0020 (12) | 0.0191 (12) | −0.0035 (12) |
| C11 | 0.0600 (19) | 0.0583 (19) | 0.0499 (17) | 0.0068 (16) | 0.0309 (16) | −0.0063 (15) |
| C12 | 0.089 (3) | 0.0476 (18) | 0.058 (2) | 0.0041 (17) | 0.039 (2) | −0.0110 (15) |
| C13 | 0.087 (3) | 0.0417 (17) | 0.061 (2) | −0.0143 (17) | 0.037 (2) | −0.0098 (15) |
| C14 | 0.064 (2) | 0.0464 (17) | 0.0532 (18) | −0.0091 (14) | 0.0324 (16) | −0.0014 (14) |
| I1 | 0.05713 (16) | 0.06921 (18) | 0.05964 (17) | −0.02284 (10) | 0.03011 (12) | −0.02193 (10) |
| N1 | 0.0480 (13) | 0.0408 (12) | 0.0341 (11) | 0.0045 (10) | 0.0222 (10) | 0.0021 (9) |
| O1 | 0.0687 (15) | 0.0578 (13) | 0.0354 (11) | 0.0109 (11) | 0.0259 (11) | 0.0079 (10) |
| O2 | 0.102 (2) | 0.0705 (16) | 0.0473 (13) | 0.0420 (16) | 0.0381 (14) | 0.0217 (12) |
| C1—O1 | 1.204 (3) | C8—O2 | 1.196 (4) |
| C1—N1 | 1.399 (4) | C8—N1 | 1.403 (3) |
| C1—C2 | 1.485 (4) | C9—C10 | 1.379 (4) |
| C2—C3 | 1.374 (4) | C9—C14 | 1.382 (4) |
| C2—C7 | 1.385 (4) | C9—N1 | 1.432 (4) |
| C3—C4 | 1.387 (5) | C10—C11 | 1.385 (4) |
| C3—H3 | 0.9300 | C10—I1 | 2.094 (3) |
| C4—C5 | 1.377 (5) | C11—C12 | 1.379 (5) |
| C4—H4 | 0.9300 | C11—H11 | 0.9300 |
| C5—C6 | 1.384 (5) | C12—C13 | 1.369 (6) |
| C5—H5 | 0.9300 | C12—H12 | 0.9300 |
| C6—C7 | 1.379 (4) | C13—C14 | 1.390 (5) |
| C6—H6 | 0.9300 | C13—H13 | 0.9300 |
| C7—C8 | 1.481 (4) | C14—H14 | 0.9300 |
| O1—C1—N1 | 124.8 (3) | N1—C8—C7 | 105.8 (2) |
| O1—C1—C2 | 129.2 (3) | C10—C9—C14 | 120.4 (3) |
| N1—C1—C2 | 106.0 (2) | C10—C9—N1 | 121.4 (3) |
| C3—C2—C7 | 121.3 (3) | C14—C9—N1 | 118.2 (3) |
| C3—C2—C1 | 130.5 (3) | C9—C10—C11 | 119.9 (3) |
| C7—C2—C1 | 108.1 (2) | C9—C10—I1 | 121.2 (2) |
| C2—C3—C4 | 117.2 (3) | C11—C10—I1 | 118.9 (2) |
| C2—C3—H3 | 121.4 | C12—C11—C10 | 119.8 (3) |
| C4—C3—H3 | 121.4 | C12—C11—H11 | 120.1 |
| C5—C4—C3 | 121.4 (3) | C10—C11—H11 | 120.1 |
| C5—C4—H4 | 119.3 | C13—C12—C11 | 120.2 (3) |
| C3—C4—H4 | 119.3 | C13—C12—H12 | 119.9 |
| C4—C5—C6 | 121.5 (3) | C11—C12—H12 | 119.9 |
| C4—C5—H5 | 119.3 | C12—C13—C14 | 120.4 (3) |
| C6—C5—H5 | 119.3 | C12—C13—H13 | 119.8 |
| C7—C6—C5 | 117.0 (3) | C14—C13—H13 | 119.8 |
| C7—C6—H6 | 121.5 | C9—C14—C13 | 119.2 (3) |
| C5—C6—H6 | 121.5 | C9—C14—H14 | 120.4 |
| C6—C7—C2 | 121.6 (3) | C13—C14—H14 | 120.4 |
| C6—C7—C8 | 129.9 (3) | C1—N1—C8 | 111.5 (2) |
| C2—C7—C8 | 108.5 (2) | C1—N1—C9 | 124.7 (2) |
| O2—C8—N1 | 125.1 (3) | C8—N1—C9 | 123.7 (2) |
| O2—C8—C7 | 129.0 (3) | ||
| O1—C1—C2—C3 | 1.0 (6) | C14—C9—C10—I1 | 179.0 (2) |
| N1—C1—C2—C3 | −178.1 (3) | N1—C9—C10—I1 | −1.4 (4) |
| O1—C1—C2—C7 | 180.0 (3) | C9—C10—C11—C12 | −0.6 (5) |
| N1—C1—C2—C7 | 0.9 (3) | I1—C10—C11—C12 | −179.4 (3) |
| C7—C2—C3—C4 | 1.5 (5) | C10—C11—C12—C13 | 0.6 (6) |
| C1—C2—C3—C4 | −179.7 (3) | C11—C12—C13—C14 | −0.2 (6) |
| C2—C3—C4—C5 | −2.2 (5) | C10—C9—C14—C13 | 0.1 (5) |
| C3—C4—C5—C6 | 1.3 (6) | N1—C9—C14—C13 | −179.5 (3) |
| C4—C5—C6—C7 | 0.5 (6) | C12—C13—C14—C9 | −0.2 (6) |
| C5—C6—C7—C2 | −1.2 (5) | O1—C1—N1—C8 | 179.7 (3) |
| C5—C6—C7—C8 | −179.4 (3) | C2—C1—N1—C8 | −1.2 (3) |
| C3—C2—C7—C6 | 0.3 (5) | O1—C1—N1—C9 | 1.3 (5) |
| C1—C2—C7—C6 | −178.8 (3) | C2—C1—N1—C9 | −179.6 (3) |
| C3—C2—C7—C8 | 178.8 (3) | O2—C8—N1—C1 | −180.0 (3) |
| C1—C2—C7—C8 | −0.3 (3) | C7—C8—N1—C1 | 1.0 (3) |
| C6—C7—C8—O2 | −1.0 (6) | O2—C8—N1—C9 | −1.5 (5) |
| C2—C7—C8—O2 | −179.4 (4) | C7—C8—N1—C9 | 179.4 (3) |
| C6—C7—C8—N1 | 178.0 (3) | C10—C9—N1—C1 | 84.2 (4) |
| C2—C7—C8—N1 | −0.4 (3) | C14—C9—N1—C1 | −96.2 (3) |
| C14—C9—C10—C11 | 0.3 (4) | C10—C9—N1—C8 | −94.1 (4) |
| N1—C9—C10—C11 | 179.9 (3) | C14—C9—N1—C8 | 85.6 (4) |
Experimental details
| Crystal data | |
| Chemical formula | C14H8INO2 |
| Mr | 349.11 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 296 |
| a, b, c (Å) | 11.5318 (5), 8.0597 (2), 15.6134 (7) |
| β (°) | 118.157 (3) |
| V (Å3) | 1279.42 (9) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 2.50 |
| Crystal size (mm) | 0.69 × 0.51 × 0.28 |
| Data collection | |
| Diffractometer | Stoe IPDS 2 diffractometer |
| Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
| Tmin, Tmax | 0.291, 0.590 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 13075, 2517, 2434 |
| Rint | 0.033 |
| (sin θ/λ)max (Å−1) | 0.617 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.078, 1.11 |
| No. of reflections | 2517 |
| No. of parameters | 163 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.82, −1.05 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), WinGX (Farrugia, 1999) and SHELXS97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
Acknowledgements
The authors thanks the Ondokuz Mayis University Research Fund for financial support of this project.
References
Devarajegowda, H. C., Revanasiddappa, H. D., Kumar, L. S., Sumangala, V. & Prasad, V. D. J. (2010). Acta Cryst. E66, o2703. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Kerrigan, J. E., Walters, M. C., Forrester, K. J., Crowder, J. B. & Christopher, L. J. (2000). Bioorg. Med. Chem. Lett. 10, 27–30. Web of Science CrossRef PubMed CAS Google Scholar
Lima, L. M., Castro, P., Machado, A. L., Fraga, C. A. M., Lugnier, C., Gonçalves de Moraes, V. L. & Barreiro, E. J. (2002). Bioorg. Med. Chem. 10, 3067–3073. Web of Science CrossRef PubMed CAS Google Scholar
Nagaraj, B., Yathirajan, H. S. & Bolte, M. (2005). Acta Cryst. E61, o928–o929. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sakthivel, P., Joseph, P. S., Sebastiyan, A., Ramesh, M. & Suvaikin, M. Y. (2007a). Acta Cryst. E63, o4284. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sakthivel, P., Joseph, P. S., Sebastiyan, A., Suvaikin, M. Y. & Ramesh, M. (2007b). Acta Cryst. E63, o4388. Web of Science CSD CrossRef 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
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
| CRYSTALLOGRAPHIC COMMUNICATIONS |
The importance of the biological activity of the phthalimide group with reference to N-2-Iodophenylphthalimide is described by Kerrigan et al., (2000) and Lima et al., (2002).
The C—C bond distances are 1.485 (4) Å for C1—C2 and 1.481 (4)Å for C7—C8. The bond distances between carbon atoms in the aromatic rings range from 1.369 (6)Å to 1.390 (5)Å. The C1=O1 and C8=O2 bond distances are 1.204 (3)Å and 1.196 (4)Å, respectively. The N—C bond distances range from 1.399 (4) Å to 1.432 (4)Å. These values are consistent with those reported in the literature (Devarajegowda et al., 2010; Sakthivel et al., 2007a; Sakthivel et al.2007b; Nagaraj et al., 2005). C10—I1 bond distance is 2.094 (3) Å. An intermolecular I1···O2 contact of 3.068 (3)Å is present in the crystal.