5-Fluoro­indoline-2,3-dione

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].

Computing details

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

Crystal data

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) Å^3	Parallelepiped, brown
Z = 4	0.30 × 0.25 × 0.25 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.166	w = 1/[σ^2(Fo^2) + (0.0891P)^2 + 0.1412P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.86	2.06	2.888 (4)	163

Symmetry code: (i) −x+1, −y+1, −z+1.