4-Formyl-2-nitrophenyl 2-chlorobenzoate

Moreno-Fuquen, Rodolfo; Hernández, Geraldine; Ellena, Javier; Simone, C. A. De; Tenório, Juan C.

doi:10.1107/s1600536813031346

Cited by 3 publications

(3 citation statements)

References 9 publications

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“…In the next step, this is changed to elastic by varying molecular orientation so that more isotropic, interlocked packing is favored . The 1D elastic crystals are next modified to two-dimensional (2D) elastic through further structural changes. − Finally, the interaction strengths , in the 2D elastic crystal are changed using known chemical principles so that the isotropy is decreased to the extent that plasticity ensues. However, because the basic structural topology is not changed, there are no slip planes in these 2D plastic bendable crystals.…”

Section: Resultsmentioning

confidence: 99%

“…Access to more than one major bendable direction (here, two) requires nearly mutual perpendicular orientations of the molecules (Figure ), in other words, a herringbone arrangement (Figure b). The literature shows that orthogonal C–H···O interactions are potential contacts to maintain such an arrangement. − Compound E3 however is seen to display only 1D elasticity, and there are no side-to-end orthogonal C–H···O interactions (see Figure S15). Then, we used the NO 2 derivative and prepared 4-iodophenyl 4-nitrobenzoate ( 3a ) and 4-iodophenyl 3-methyl-4-nitrobenzoate ( 3b ) (Figure ).…”

Section: Resultsmentioning

confidence: 99%

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Crystal Engineering of Hand-Twisted Helical Crystals

2017

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A strategy is outlined for the design of hand-twisted helical crystals. The starting point in the exercise is the one-dimensional (1D) plastic crystal, 1,4-dibromobenzene, which is then changed to a 1D elastic crystal, exemplified by 4-bromophenyl 4'-chlorobenzoate, by introduction of a molecular synthon -O-CO- in lieu of the supramolecular synthon Br···Br in the precursor. The 1D elastic crystals are next modified to two-dimensional (2D) elastic crystals, of the type 4-bromophenyl 4'-nitrobenzoate where the halogen bonding and C-H···O hydrogen bonding are well-matched. Finally, varying the interaction strengths in these 2D elastic crystals gives plastic crystals with two pairs of bendable faces but without slip planes. Typical examples are 4-chlorophenyl and 4-bromophenyl 4'-nitrobenzoate. This type of 2D plasticity represents a new type of bendable crystals in which plastic behavior is seen with a fair degree of isotropic character in the crystal packing. The presence of two sets of bendable faces, generally orthogonal to each other, allows for the possibility of hand-twisting of the crystals to give grossly helical morphologies. Accordingly, we propose the name hand-twisted helical crystals for these substances.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Crystal Engineering of Hand-Twisted Helical Crystals

2017

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“…(Moreno- Fuquen et al, 2013a), 4-formyl-2-nitrophenyl 4-cloro benzoate (F4ClB)(Moreno-Fuquen et al, 2013b) and 4-formyl-2nitrophenyl 3-nitro-2-methyl benzoate (F3N2MB)(Moreno-Fuquen et al, 2014) reported earlier jobs. The benzene rings of (I) form a dihedral angle of 46.36 (8)°.…”

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4-Formyl-2-nitrophenyl benzoate

2014

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In the title nitroaryl benzoate derivative, C14H9NO5, the aromatic rings form a dihedral angle of 46.37 (8)°. The central ester moiety, —C—(C=O)—O—, is essentially planar (r.m.s. deviation for all non-H atoms = 0.0283 Å) and forms a dihedral angle of 54.06 (9)° with the 4-formyl-2-nitrophenyl ring and 7.99 (19)° with the benzoate ring. In the crystal, molecules are intertwined by weak C—H⋯O interactions, forming helical chains along [100].

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4-Formyl-2-nitrophenyl 3-nitro-2-methylbenzoate

Moreno-Fuquen¹,

Hernández²,

Kennedy³

2013

Acta Cryst E

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In the title formyl nitro aryl benzoate derivative, C15H10N2O7, the benzene rings form a dihedral angle of 4.96 (3)°. The mean plane of the central ester group, C—O—C–(=O)—C (r.m.s. deviation = 0.0484 Å), is twisted away from the formyl nitro aryl and benzoate rings by 46.61 (5) and 49.93 (5)°, respectively. In the crystal, the molecules are packed forming C—H⋯O interactions in chains which propagate along [010]. Edge-fused R 3 3(15) rings are generated along this direction.

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4-Formyl-2-nitrophenyl 2-chlorobenzoate

Cited by 3 publications

References 9 publications

Crystal Engineering of Hand-Twisted Helical Crystals

Crystal Engineering of Hand-Twisted Helical Crystals

4-Formyl-2-nitrophenyl benzoate

4-Formyl-2-nitrophenyl 3-nitro-2-methylbenzoate

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