organic compounds
6-Fluoro-1H-indole-2,3-dione
aDepartment of Chemistry and Biochemistry, University of Massachusetts Dartmouth, 285 Old Westport Road, North Dartmouth, MA 02747, USA
*Correspondence e-mail: dmanke@umassd.edu
The title compound, C8H4FNO2, has a single, almost planar, molecule in the with the non-H atoms having a mean deviation from planarity of 0.042 Å. Intermolecular N—H⋯O hydrogen bonds result in infinite chains along [100]. The molecules are further linked through weak C—H⋯O and C—H⋯F interactions.
Keywords: crystal structure; hydrogen bonding; isatins.
CCDC reference: 1450254
Structure description
Herein we report the ). The bond lengths and angles were similar to those observed in the parent isatin (Goldschmidt et al., 1950). In the crystal, the molecule exhibits N1—H1⋯O1 hydrogen bonds that result in infinite chains along [100]. There are also C7—H7⋯O2 interactions and C5—H5⋯F1 interactions that further link the molecules in the solid state (Table 1, Fig. 2). These C—H⋯F interactions are unique to this class of compounds as there are no halogen interactions reported in other fluoroisatin derivatives (Mohamed et al., 2007a,b; Shankland et al., 2007; Wu et al., 2011; Wang et al., 2012; Mudududdla et al., 2014). The structure of the only other 6-haloisatin reported, 6-bromoisatin, also possesses a halogen interaction, with a Br⋯O close contact being observed (Turbitt et al., 2016).
of 6-fluoroisatin as part of a continuing study on the structure of halogenated isatins. The structure exhibits a near planar molecule with the non-hydrogen atoms possessing a mean deviation from planarity of 0.042 Å (Fig. 1Synthesis and crystallization
A commercial sample (Matrix Scientific) of 6-fluoro-1H-indole-2,3-dione was used for the crystallization. A sample suitable for single-crystal X-ray analysis was grown from the slow evaporation of its acetone solution.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1450254
https://doi.org/10.1107/S2414314616001656/sj4011sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616001656/sj4011Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616001656/sj4011Isup3.cml
Data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).C8H4FNO2 | Dx = 1.633 Mg m−3 |
Mr = 165.12 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, P212121 | Cell parameters from 6268 reflections |
a = 4.9880 (3) Å | θ = 5.5–68.3° |
b = 5.5522 (3) Å | µ = 1.19 mm−1 |
c = 24.2578 (12) Å | T = 298 K |
V = 671.80 (6) Å3 | BLOCK, orange |
Z = 4 | 0.25 × 0.15 × 0.1 mm |
F(000) = 336 |
Bruker D8 Venture CMOS diffractometer | 1205 independent reflections |
Radiation source: Cu | 1184 reflections with I > 2σ(I) |
HELIOS MX monochromator | Rint = 0.043 |
φ and ω scans | θmax = 68.3°, θmin = 9.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −6→5 |
Tmin = 0.528, Tmax = 0.753 | k = −6→6 |
7354 measured reflections | l = −29→29 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0688P)2 + 0.1919P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.112 | (Δ/σ)max < 0.001 |
S = 1.10 | Δρmax = 0.49 e Å−3 |
1205 reflections | Δρmin = −0.23 e Å−3 |
112 parameters | Absolute structure: Flack x determined using 451 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.03 (7) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
F1 | 0.0765 (5) | 0.5676 (5) | 0.70923 (9) | 0.0721 (7) | |
O1 | 1.0503 (4) | 0.4748 (4) | 0.50142 (8) | 0.0409 (5) | |
O2 | 1.0523 (4) | 0.0601 (4) | 0.57698 (9) | 0.0438 (6) | |
N1 | 0.6855 (5) | 0.5829 (4) | 0.55480 (9) | 0.0345 (6) | |
H1 | 0.644 (7) | 0.712 (4) | 0.5368 (11) | 0.041* | |
C1 | 0.8919 (5) | 0.4412 (5) | 0.53884 (10) | 0.0317 (6) | |
C2 | 0.8971 (6) | 0.2246 (4) | 0.57986 (10) | 0.0310 (6) | |
C3 | 0.6835 (5) | 0.2782 (5) | 0.61916 (10) | 0.0327 (6) | |
C4 | 0.6008 (7) | 0.1608 (5) | 0.66655 (11) | 0.0398 (7) | |
H4 | 0.6838 | 0.0190 | 0.6777 | 0.048* | |
C5 | 0.3914 (7) | 0.2583 (6) | 0.69712 (12) | 0.0467 (7) | |
H5 | 0.3297 | 0.1827 | 0.7289 | 0.056* | |
C6 | 0.2774 (6) | 0.4711 (7) | 0.67891 (11) | 0.0432 (7) | |
C7 | 0.3538 (6) | 0.5951 (6) | 0.63205 (12) | 0.0398 (7) | |
H7 | 0.2705 | 0.7371 | 0.6211 | 0.048* | |
C8 | 0.5624 (5) | 0.4936 (5) | 0.60257 (10) | 0.0308 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0613 (12) | 0.0928 (17) | 0.0622 (12) | 0.0084 (15) | 0.0169 (10) | −0.0181 (12) |
O1 | 0.0407 (11) | 0.0395 (10) | 0.0426 (10) | −0.0048 (9) | 0.0053 (8) | 0.0086 (9) |
O2 | 0.0450 (11) | 0.0342 (10) | 0.0522 (11) | 0.0089 (10) | −0.0021 (9) | 0.0043 (9) |
N1 | 0.0393 (12) | 0.0250 (11) | 0.0394 (12) | 0.0020 (10) | −0.0016 (10) | 0.0107 (9) |
C1 | 0.0330 (12) | 0.0272 (12) | 0.0348 (12) | −0.0046 (11) | −0.0039 (10) | 0.0040 (10) |
C2 | 0.0329 (12) | 0.0251 (12) | 0.0349 (12) | −0.0017 (12) | −0.0048 (11) | 0.0026 (10) |
C3 | 0.0345 (13) | 0.0290 (13) | 0.0346 (13) | −0.0024 (12) | −0.0036 (11) | 0.0027 (10) |
C4 | 0.0482 (16) | 0.0348 (14) | 0.0365 (13) | −0.0038 (14) | −0.0022 (14) | 0.0090 (11) |
C5 | 0.0508 (17) | 0.0541 (16) | 0.0354 (13) | −0.0104 (18) | 0.0032 (13) | 0.0026 (13) |
C6 | 0.0373 (14) | 0.0546 (19) | 0.0377 (14) | −0.0023 (14) | 0.0031 (11) | −0.0128 (13) |
C7 | 0.0388 (16) | 0.0349 (14) | 0.0458 (14) | 0.0032 (13) | −0.0060 (13) | −0.0059 (11) |
C8 | 0.0321 (13) | 0.0265 (12) | 0.0337 (12) | −0.0022 (11) | −0.0055 (10) | 0.0006 (10) |
F1—C6 | 1.353 (4) | C3—C8 | 1.399 (4) |
O1—C1 | 1.218 (3) | C4—H4 | 0.9300 |
O2—C2 | 1.199 (3) | C4—C5 | 1.391 (5) |
N1—H1 | 0.864 (13) | C5—H5 | 0.9300 |
N1—C1 | 1.352 (4) | C5—C6 | 1.383 (5) |
N1—C8 | 1.402 (3) | C6—C7 | 1.382 (4) |
C1—C2 | 1.561 (3) | C7—H7 | 0.9300 |
C2—C3 | 1.460 (4) | C7—C8 | 1.383 (4) |
C3—C4 | 1.384 (4) | ||
C1—N1—H1 | 121 (2) | C5—C4—H4 | 120.5 |
C1—N1—C8 | 111.4 (2) | C4—C5—H5 | 121.0 |
C8—N1—H1 | 127 (2) | C6—C5—C4 | 118.1 (3) |
O1—C1—N1 | 128.2 (2) | C6—C5—H5 | 121.0 |
O1—C1—C2 | 125.6 (2) | F1—C6—C5 | 118.0 (3) |
N1—C1—C2 | 106.2 (2) | F1—C6—C7 | 117.0 (3) |
O2—C2—C1 | 124.1 (2) | C7—C6—C5 | 125.1 (3) |
O2—C2—C3 | 131.6 (2) | C6—C7—H7 | 122.3 |
C3—C2—C1 | 104.3 (2) | C6—C7—C8 | 115.5 (3) |
C4—C3—C2 | 131.6 (3) | C8—C7—H7 | 122.3 |
C4—C3—C8 | 120.8 (3) | C3—C8—N1 | 110.6 (2) |
C8—C3—C2 | 107.5 (2) | C7—C8—N1 | 127.8 (3) |
C3—C4—H4 | 120.5 | C7—C8—C3 | 121.6 (2) |
C3—C4—C5 | 118.9 (3) | ||
F1—C6—C7—C8 | 179.0 (2) | C2—C3—C8—C7 | −179.1 (2) |
O1—C1—C2—O2 | −3.9 (4) | C3—C4—C5—C6 | −0.8 (4) |
O1—C1—C2—C3 | 175.1 (3) | C4—C3—C8—N1 | 177.9 (2) |
O2—C2—C3—C4 | 3.0 (5) | C4—C3—C8—C7 | −1.1 (4) |
O2—C2—C3—C8 | −179.4 (3) | C4—C5—C6—F1 | −179.0 (3) |
N1—C1—C2—O2 | 178.2 (3) | C4—C5—C6—C7 | 0.6 (5) |
N1—C1—C2—C3 | −2.8 (3) | C5—C6—C7—C8 | −0.6 (5) |
C1—N1—C8—C3 | −1.9 (3) | C6—C7—C8—N1 | −177.9 (3) |
C1—N1—C8—C7 | 177.0 (3) | C6—C7—C8—C3 | 0.8 (4) |
C1—C2—C3—C4 | −176.0 (3) | C8—N1—C1—O1 | −175.0 (3) |
C1—C2—C3—C8 | 1.7 (3) | C8—N1—C1—C2 | 2.8 (3) |
C2—C3—C4—C5 | 178.4 (3) | C8—C3—C4—C5 | 1.1 (4) |
C2—C3—C8—N1 | −0.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 (1) | 2.03 (1) | 2.889 (3) | 177 (3) |
C5—H5···F1ii | 0.93 | 2.60 | 3.425 (4) | 148 |
C7—H7···O2iii | 0.93 | 2.36 | 3.273 (4) | 169 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x, y−1/2, −z+3/2; (iii) x−1, y+1, z. |
Acknowledgements
We greatly acknowledge support from the National Science Foundation (CHE-1429086)
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