<i>N</i>-(4-Fluorophenyl)-4-nitrophthalimide: tripartite hydrogen-bonded sheets

Glidewell, Christopher; Low, John N.; Skakle, Janet M. S.; Wardell, James L.

doi:10.1107/s0108270104013575

Cited by 31 publications

(36 citation statements)

References 5 publications

(2 reference statements)

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“…The dihedral angle between the planar benzene (C9-C14) and pyridine (N3, C3-C7) rings in 3 is 44.5(1) . The S-O and S-N bond distances in 3 [ Table 3] are similar to that reported for analogous structures [11][12][13]. Mechanistically, it was not clearly understood how the compound 3 formed during the reaction of piroxicam 1 with benzoyl chloride.…”

Section: Resultssupporting

confidence: 69%

Synthesis and structure analysis of cyclodehydration product of piroxicam: A metabolite detected in dogs and monkeys

Pal

Bindu

Dubey

et al. 2009

European Journal of Medicinal Chemistry

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Section: Resultssupporting

confidence: 69%

Synthesis and structure analysis of cyclodehydration product of piroxicam: A metabolite detected in dogs and monkeys

Pal

Bindu

Dubey

et al. 2009

European Journal of Medicinal Chemistry

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“…ring has been reported previously (see for example the recent publication by Glidewell et al, 2004).…”

Section: Figuresupporting

confidence: 58%

Solid solution of two diastereomers of [3a(R,S),7a(R,S)]-3-[(1′R)-1-phenylethyl]perhydro-1,3-benzothiazol-2-iminium chloride

Plutecka¹,

Rychłewska²,

Prusinowska³

et al. 2010

Acta Crystallogr Sect B

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A mixture of two diastereomers with the configurations (3aS,7aS,1'R) and (3aR,7aR,1'R) forms co-crystals in which there is one unique molecule in the asymmetric unit, but the molecule displays disorder which is a result of the presence of the two diastereomers at the same crystallographic site. Theoretical calculations carried out by the DFT method with the 6-311++G(2df,p) basis set allowed for the estimation of the energy difference between the two diastereomers both in the isolated and the solid state, while the natural bond orbital (NBO), Mulliken, natural population (NPA) and CHelpG analyses helped to establish the electronic structure of the thazolidin-2-imine fragment.

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“…The primary intermediate in such a reaction is an acid of type (G), see Scheme 3; hydrolysis of (G) can give an anilinium salt (H) or, alter-natively, loss of water from (G) can give the N-arylphthalimide (J). We have recently reported the supramolecular structures of representative examples of type (G) (Glidewell et al, 2004b) and (H) (Glidewell et al, 2003c), while the six isomeric compounds (I)-(VI) discussed in this paper are representative of form (J).…”

Section: Introductionmentioning

confidence: 91%

Isomeric N-(iodophenyl)nitrophthalimides: interplay of C—H...O hydrogen bonds, iodo...nitro and iodo...carbonyl interactions, and aromatic π...π stacking interactions

Glidewell

Low

Skakle

et al. 2005

Acta Crystallogr Sect B

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The six isomeric N-(iodophenyl)nitrophthalimides, C(14)H(7)IN(2)O(4), have been synthesized and the structures of five of them are reported. In N-(4-iodophenyl)-4-nitrophthalimide [(I), orthorhombic P2(1)2(1)2(1)] the molecules are linked into sheets by a combination of four independent C-H...O hydrogen bonds, but I...O interactions are absent. The isomers N-(3-iodophenyl)-4-nitrophthalimide [(II), monoclinic P2(1)/c] and N-(2-iodophenyl)-4-nitrophthalimide [(III), monoclinic P2(1)/n] both form sheets, but in (II) the molecules are linked by a combination of one two-centre iodo...nitro interaction and one C-H...O hydrogen bond into sheets containing R_4/4(30) rings, while in (III) they are linked by an iodo...carbonyl interaction and a C-H...O hydrogen bond into sheets or R_4/4(26) rings. Three-dimensional supramolecular structures are formed in both N-(4-iodophenyl)-3-nitrophthalimide [(IV), monoclinic P2(1)/n] and N-(3-iodophenyl)-3-nitrophthalimide [(V), orthorhombic, P2(1)2(1)2(1)]. In (IV) the molecules are linked by a three-centre iodo...nitro interaction, three C-H...O hydrogen bonds and an aromatic pi...pi stacking interaction, but the framework in (V) is generated by a two-centre iodo...nitro interaction and only two C-H...O hydrogen bonds: aromatic pi...pi stacking interactions are absent from (V).

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N-(4-Fluorophenyl)-4-nitrophthalimide: tripartite hydrogen-bonded sheets

Cited by 31 publications

References 5 publications

Synthesis and structure analysis of cyclodehydration product of piroxicam: A metabolite detected in dogs and monkeys

Synthesis and structure analysis of cyclodehydration product of piroxicam: A metabolite detected in dogs and monkeys

Solid solution of two diastereomers of [3a(R,S),7a(R,S)]-3-[(1′R)-1-phenylethyl]perhydro-1,3-benzothiazol-2-iminium chloride

Isomeric N-(iodophenyl)nitrophthalimides: interplay of C—H...O hydrogen bonds, iodo...nitro and iodo...carbonyl interactions, and aromatic π...π stacking interactions

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