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In the title compound (5-fluoroisatin), C8H4FNO2, the N atom of one molecule is linked to the amido-O atom of an adjacent molecule across a center of symmetry by a cyclic hydrogen bond [N
O = 2.888 (4) Å].
O = 2.888 (4) Å].Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010568/qd0008sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010568/qd0008Isup2.hkl |
CCDC reference: 150740
Computing details top
Data collection: XDS (Kabsch, 1988); cell refinement: XDS; data reduction: XDS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
5-Fluoro-2,3-indolinedione top
Crystal data top
| C8H4FNO2 | F(000) = 336 |
| Mr = 165.12 | Dx = 1.587 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 3.789 (7) Å | Cell parameters from 2310 reflections |
| b = 12.20 (1) Å | θ = 2.2–26.0° |
| c = 14.99 (2) Å | µ = 0.13 mm−1 |
| β = 94.41 (1)° | T = 298 K |
| V = 691 (2) Å3 | Parallelepiped, brown |
| Z = 4 | 0.30 × 0.25 × 0.25 mm |
Data collection top
| MarResearch Image Plate diffractometer | 851 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.034 |
| Graphite monochromator | θmax = 26.0°, θmin = 2.2° |
| Method: 95 frames at 2° intervals, counting time 2 min. scans | h = 0→4 |
| 2310 measured reflections | k = −15→14 |
| 1265 independent reflections | l = −18→18 |
Refinement top
| 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)] = 0.053 | H-atom parameters constrained |
| wR(F2) = 0.166 | w = 1/[σ2(Fo2) + (0.0891P)2 + 0.1412P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max < 0.001 |
| 1265 reflections | Δρmax = 0.20 e Å−3 |
| 110 parameters | Δρmin = −0.19 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.04 (1) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| F1 | 0.3855 (6) | 1.0281 (2) | 0.2614 (1) | 0.0844 (7) | |
| O1 | 0.9244 (6) | 0.8277 (2) | 0.5724 (1) | 0.0685 (7) | |
| O2 | 0.7484 (6) | 0.5926 (2) | 0.5759 (1) | 0.0708 (7) | |
| N1 | 0.4707 (6) | 0.6339 (2) | 0.4371 (1) | 0.0537 (7) | |
| C1 | 0.4261 (7) | 0.7294 (2) | 0.3836 (2) | 0.0443 (7) | |
| C2 | 0.2582 (7) | 0.7380 (2) | 0.2989 (2) | 0.0511 (7) | |
| C3 | 0.2485 (7) | 0.8403 (3) | 0.2589 (2) | 0.0541 (7) | |
| C4 | 0.4036 (8) | 0.9289 (2) | 0.3041 (2) | 0.0549 (8) | |
| C5 | 0.5729 (7) | 0.9227 (2) | 0.3879 (2) | 0.0524 (7) | |
| C6 | 0.5829 (6) | 0.8200 (2) | 0.4278 (2) | 0.0431 (7) | |
| C7 | 0.7472 (7) | 0.7809 (2) | 0.5134 (2) | 0.0477 (7) | |
| C8 | 0.6606 (8) | 0.6565 (2) | 0.5154 (2) | 0.0530 (7) | |
| H1 | 0.3885 | 0.5703 | 0.4220 | 0.064* | |
| H2 | 0.1552 | 0.6773 | 0.2698 | 0.061* | |
| H3 | 0.1381 | 0.8495 | 0.2018 | 0.065* | |
| H5 | 0.6753 | 0.9838 | 0.4165 | 0.063* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| F1 | 0.115 (2) | 0.061 (1) | 0.076 (1) | −0.001 (1) | −0.002 (1) | 0.024 (1) |
| O1 | 0.084 (2) | 0.069 (1) | 0.050 (1) | −0.015 (1) | −0.015 (1) | −0.009 (1) |
| O2 | 0.099 (2) | 0.061 (1) | 0.048 (1) | −0.012 (1) | −0.021 (1) | 0.010 (1) |
| N1 | 0.072 (2) | 0.043 (1) | 0.044 (1) | −0.008 (1) | −0.011 (1) | 0.001 (1) |
| C1 | 0.050 (2) | 0.045 (2) | 0.038 (1) | −0.004 (1) | 0.003 (1) | −0.002 (1) |
| C2 | 0.056 (2) | 0.054 (2) | 0.042 (2) | −0.001 (1) | −0.003 (1) | −0.007 (1) |
| C3 | 0.058 (2) | 0.066 (2) | 0.037 (1) | 0.006 (1) | 0.000 (1) | 0.002 (1) |
| C4 | 0.067 (2) | 0.048 (2) | 0.051 (2) | 0.007 (1) | 0.009 (1) | 0.012 (1) |
| C5 | 0.060 (2) | 0.048 (2) | 0.050 (2) | −0.003 (1) | 0.009 (1) | −0.002 (1) |
| C6 | 0.047 (1) | 0.043 (1) | 0.039 (1) | −0.003 (1) | 0.003 (1) | −0.003 (1) |
| C7 | 0.052 (2) | 0.051 (2) | 0.040 (1) | −0.004 (1) | −0.001 (1) | −0.005 (1) |
| C8 | 0.062 (2) | 0.057 (2) | 0.039 (1) | −0.007 (1) | −0.005 (1) | 0.002 (1) |
Geometric parameters (Å, º) top
| F1—C4 | 1.368 (3) | C4—C5 | 1.368 (4) |
| O1—C7 | 1.211 (3) | C5—C6 | 1.388 (4) |
| O2—C8 | 1.222 (3) | C6—C7 | 1.463 (4) |
| N1—C1 | 1.417 (3) | C7—C8 | 1.554 (4) |
| N1—C8 | 1.356 (4) | N1—H1 | 0.8600 |
| C1—C2 | 1.378 (4) | C2—H2 | 0.9300 |
| C1—C6 | 1.398 (4) | C3—H3 | 0.9300 |
| C2—C3 | 1.385 (4) | C5—H5 | 0.9300 |
| C3—C4 | 1.382 (4) | ||
| C8—N1—C1 | 110.8 (2) | O1—C7—C6 | 131.4 (3) |
| C2—C1—C6 | 121.7 (3) | O1—C7—C8 | 123.6 (2) |
| C2—C1—N1 | 127.6 (2) | C6—C7—C8 | 105.0 (2) |
| C6—C1—N1 | 110.7 (2) | O2—C8—N1 | 127.5 (3) |
| C1—C2—C3 | 117.5 (3) | O2—C8—C7 | 126.2 (2) |
| C2—C3—C4 | 119.8 (3) | N1—C8—C7 | 106.3 (2) |
| C5—C4—F1 | 118.8 (3) | C8—N1—H1 | 124.6 |
| C5—C4—C3 | 124.0 (3) | C1—C2—H2 | 121.2 |
| F1—C4—C3 | 117.3 (3) | C3—C2—H2 | 121.2 |
| C4—C5—C6 | 116.2 (3) | C4—C3—H3 | 120.1 |
| C5—C6—C1 | 120.9 (2) | C2—C3—H3 | 120.1 |
| C5—C6—C7 | 131.9 (2) | C4—C5—H5 | 121.9 |
| C1—C6—C7 | 107.1 (2) | C6—C5—H5 | 121.9 |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O2i | 0.86 | 2.06 | 2.888 (4) | 163 |
| Symmetry code: (i) −x+1, −y+1, −z+1. |
