Crystal structure of flumioxazin

Hyunjin Park; Jineun Kim; Eunjin Kwon; Tae Ho Kim

doi:10.1107/S2056989015017223

. 2015 Sep 17;71(Pt 10):o768. doi: 10.1107/S2056989015017223

Crystal structure of flumioxazin

Hyunjin Park ^a, Jineun Kim ^a,^*, Eunjin Kwon ^a, Tae Ho Kim ^a,^*

PMCID: PMC4647385 PMID: 26594468

Abstract

The title compound {systematic name: 2-[7-fluoro-3,4-dihydro-3-oxo-4-(prop-2-yn-1-yl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione}, C₁₉H₁₅FN₂O₄, is a dicarboximide herbicide. The dihedral angle between the maleimide and benzene ring planes is 66.13 (5)°. In the crystal, C—H⋯O and C—H⋯F hydrogen bonds and weak C—H⋯π interactions [3.5601 (19) Å] link adjacent molecules, forming two-dimensional networks extending parallel to the (110) plane.

Keywords: crystal structure; dicarboximide herbicide; flumioxazin; 1H-isoindole; 1,4-benzoxazine; C—H⋯F hydrogen bonds

Related literature

For information on the herbicidal properties of the title compound, see: Saladin et al. (2003 ▸); Geoffroy et al. (2004 ▸). For a related crystal structure, see: Hou et al. (2004 ▸). graphic file with name e-71-0o768-scheme1.jpg

Experimental

Crystal data

C₁₉H₁₅FN₂O₄
M _r = 354.33
Monoclinic,
a = 8.896 (1) Å
b = 7.1592 (8) Å
c = 25.708 (3) Å
β = 96.039 (6)°
V = 1628.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 173 K
0.50 × 0.26 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T _min = 0.575, T _max = 0.746
27372 measured reflections
4067 independent reflections
3277 reflections with I > 2σ(I)
R _int = 0.067

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.137
S = 1.07
4067 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: DIAMOND (Brandenburg, 2010 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015017223/hb7502sup1.cif

e-71-0o768-sup1.cif^{(847.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015017223/hb7502Isup2.hkl

e-71-0o768-Isup2.hkl^{(223.1KB, hkl)}

Click here for additional data file.^{(6.7KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015017223/hb7502Isup3.cml

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S2056989015017223/hb7502fig1.tif

The asymmetric unit of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

Click here for additional data file.^{(1.2MB, tif)}

c . DOI: 10.1107/S2056989015017223/hb7502fig2.tif

Crystal packing viewed along the c axis. The intermolecular interactions are shown as dashed lines.

CCDC reference: 1424397

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

Cg1 is the centroid of the C3/C4/C8C11 ring.

DHA	DH	HA	D A	DHA
C7H7O4ⁱ	0.95	2.39	3.178(2)	140
C19H19BF1ⁱⁱ	0.99	2.36	3.289(2)	155
C16H16A Cg1ⁱⁱⁱ	0.99	2.63	3.5601(19)	157

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2015R1D1A4A01020317).

supplementary crystallographic information

S1. Comment

Flumioxazin [systematic name: 2-[7-fluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione] is a soil applied pre-emergent herbicide used to inhibit development of redroot pigweed. (Geoffroy et al., 2004; Saladin et al., 2003). However, its crystal structure has not been reported until now. In the title compound (Fig. 1), the dihedral angle between pyrrole and benzne rings is 66.13 (5)°. All bond lengths and bond angles are normal and comparable to those observed in a similar crystal structure (Hou et al., 2004).

In the crystal structure (Fig. 2), C—H···O and C—H···F hydrogen bonds and weak C–H···π interactions are observed (Table 1). Two-dimensional networks are formed by the hydrogen bonds and weak C–H···π interactions.

S2. Experimental

The title compound was purchased from the Dr Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH₃CN gave single crystals suitable for X-ray analysis.