2-[7-Fluoro-3,4-dihydro-4-(3-iodoprop-2-ynyl)-3-oxo-2<i>H</i>-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-2<i>H</i>-isoindole-1,3-dione

Hou, Zhuang; Ren, Yulin; Huang, Ming-Zhi; Song, Jian; Chen, Ligong

doi:10.1107/s160053680401637x

Cited by 3 publications

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“…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).…”

Section: Related Literaturesupporting

confidence: 81%

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Crystal structure of flumioxazin

et al. 2015

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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.

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Section: Related Literaturesupporting

confidence: 81%

“…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 Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of flumioxazin

et al. 2015

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Intramolecular N–H···O and N–H···N hydrogen bonding patterns in N-benzyl and N-(pyridin-2-ylmethyl) benzamides

Jiang

2009

Tetrahedron Letters

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Diiodoacetylene: compact, strong ditopic halogen bond donor

et al. 2012

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Diiodoacetylene, C 2 I 2 , is the smallest ditopic halogen bond donor other than I 2 or other dihalogens. A convenient synthesis of diiodoacetylene from the common Sonagashira coupling reagent Me 3 SiChCH, is described. The halogen-bonded adducts of C 2 I 2 with dimethylformamide (DMF), pyrazine (pyz) and 1,4-diazabicyclooctane (dabco) have been characterised by X-ray crystallography. All adopt 1D halogen-bonded chains linked via short C-I/O [I/O 2.834(4)-2.888(4) A; C-I/O > 170 ] or C-I/N [I/N 2.715(3)-2.832(7) A; C-I/N > 175 ] interactions. Attempts to synthesise the adduct of C 2 I 2 with hexamethylenetetramine (hmta) resulted in isolation and crystallographic characterisation of the adduct of C 2 I 4 $hmta, indicating decomposition of C 2 I 2 to yield C 2 I 4 in solution. The adduct comprises two independent C 2 I 4 molecules that act, respectively, as tetratopic and ditopic halogen bond donors forming C-I/N interactions [I/N 2.948(7)-2.999(8) A; C-I/N > 165 ], occupying three of the four nitrogen sites on htma. The remaining nitrogen sites engage in N/C(p) interactions directed orthogonal to the plane of the ditopic C 2 I 4 molecules. Separate surveys of halogen bonds formed by diiodo(poly)alkynes I(ChC) n I (n ¼ 1-3) and by C 2 I 4 molecules indicate that C-I/N halogen bonds are shorter, when normalised for van der Waals radii, and, by inference, stronger than halogen bonds involving other acceptor groups, and demonstrates that C sp -I/N halogen bonds are generally shorter C sp 2-I/N halogen bonds.

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2-[7-Fluoro-3,4-dihydro-4-(3-iodoprop-2-ynyl)-3-oxo-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione

Abstract: The title compound, C19H14FIN2O4, known as a protox inhibitor, was synthesized from flumioxazin. The cyclohexene ring in the molecule is in a distorted chair conformation. The molecules are connected into two‐dimensional layers by C=O⋯I interactions.

Cited by 3 publications

References 2 publications

Crystal structure of flumioxazin

Crystal structure of flumioxazin

Intramolecular N–H···O and N–H···N hydrogen bonding patterns in N-benzyl and N-(pyridin-2-ylmethyl) benzamides

Diiodoacetylene: compact, strong ditopic halogen bond donor

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2-[7-Fluoro-3,4-dihydro-4-(3-iodoprop-2-ynyl)-3-oxo-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione

Abstract: The title compound, C19H14FIN2O4, known as a protox inhibitor, was synthesized from flumioxazin. The cyclo­hexene ring in the mol­ecule is in a distorted chair conformation. The mol­ecules are connected into two‐dimensional layers by C=O⋯I interactions.

Cited by 3 publications

References 2 publications

Crystal structure of flumioxazin

Crystal structure of flumioxazin

Intramolecular N–H···O and N–H···N hydrogen bonding patterns in N-benzyl and N-(pyridin-2-ylmethyl) benzamides

Diiodoacetylene: compact, strong ditopic halogen bond donor

Contact Info

Product

Resources

About

Abstract: The title compound, C19H14FIN2O4, known as a protox inhibitor, was synthesized from flumioxazin. The cyclohexene ring in the molecule is in a distorted chair conformation. The molecules are connected into two‐dimensional layers by C=O⋯I interactions.