<i>N</i>-[4-(2,2-Dimethylpropionylamino)phenyl]-2,2-dimethylpropionamide

Guo, Hui-Zhen; Yin, Guodong; She, Neng-Fang; Wu, An‐Xin

doi:10.1107/s1600536805035993

Cited by 3 publications

(11 citation statements)

References 3 publications

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“…Fig. 2presents a packing view showing the main H bonding interactions in the structure(Table 1): a weak intramolecular N-H•••F contact, somehow anchoring the rotation of the C-F 3 group, and a stronger intermolecular N-H•••O H-bond, linking molecules into chains along [100] The O•••H distance of 2.15 (3) Å is similar to values reported in related compounds [2.14 (1) Å;Guo et al, 2005].…”

supporting

confidence: 58%

“…For the preparation of the title compound, see: Guo et al (2005). For related literature, see: Allen et al (1987); Frederick & Liu (1999).…”

Section: Related Literaturementioning

confidence: 99%

“…The title compound was synthesized according to the procedure of Guo, et al (2005). Crystals of (I) suitable for X-ray data collection were obtained by slow evaporation of a CH 2 Cl 2 and MeOH solution in a ratio of 2:1 at 293 K.…”

Section: S2 Experimentalmentioning

confidence: 99%

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N,N′-(p-Phenylene)bis(2,2,2-trifluoroacetamide)

Huang¹,

Lü²

2007

Acta Cryst E

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supporting

confidence: 58%

“…For the preparation of the title compound, see: Guo et al (2005). For related literature, see: Allen et al (1987); Frederick & Liu (1999).…”

Section: Related Literaturementioning

confidence: 99%

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N,N′-(p-Phenylene)bis(2,2,2-trifluoroacetamide)

Huang¹,

Lü²

2007

Acta Cryst E

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“…Along the c ‐axis only weak van der Waals interactions are detected. Within series 2 one molecule builds four hydrogen bonds to four other molecules as reported within references [34–37] . This leads to a fence‐like crossing pattern with the hydrogen bonds propagating along the b ‐axis.…”

Section: Resultsmentioning

confidence: 76%

“…This implies the growth of an object with one preferred growth rate and an anisotropic morphology. In the second case, the twisted arrangement of the five molecules involved in the supramolecular synthon induces packings with strong interactions in two dimensions [34–37] …”

Section: Introductionmentioning

confidence: 99%

Crystal Engineering of Supramolecular 1,4‐Benzene Bisamides by Side‐Chain Modification – Towards Tuneable Anisotropic Morphologies and Surfaces

et al. 2021

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Benzene bisamides are promising building blocks for supramolecular nano‐objects. Their functionality depends on morphology and surface properties. However, a direct link between surface properties and molecular structure itself is missing for this material class. Here, we investigate this interplay for two series of 1,4‐benzene bisamides with symmetric and asymmetric peripheral substitution. We elucidated the crystal structures, determined the nano‐object morphologies and derived the wetting behaviour of the preferentially exposed surfaces. The crystal structures were solved by combining single‐crystal and powder X‐ray diffraction, solid‐state NMR spectroscopy and computational modelling. Bulky side groups, here t‐butyl groups, serve as a structure‐directing motif into a packing pattern, which favours the formation of thin platelets. The use of slim peripheral groups on both sides, in our case linear perfluorinated, alkyl chains, self‐assemble the benzene bisamides into a second packing pattern which leads to ribbon‐like nano‐objects. For both packing types, the preferentially exposed surfaces consist of the ends of the peripheral groups. Asymmetric substitution with bulky and slim groups leads to an ordered alternating arrangement of the groups exposed to the surface. This allows the hydrophobicity of the surfaces to be gradually altered. We thus identified two leitmotifs for molecular packings of benzene bisamides providing the missing link between the molecular structure, the anisotropic morphologies and adjustable surface properties of the supramolecular nano‐objects.

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NMR-crystallographic study of two-dimensionally self-assembled cyclohexane-based low-molecular-mass organic compounds

et al. 2013

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Using a combined approach based on scanning electron microscopy, powder X-ray diffraction as well as 1D and 2D multinuclear solid-state NMR spectroscopy, we were able to determine the morphology and the crystal structures for a set of three supramolecular compounds with different hydrogen bonding motifs, namely N,N′-(cyclohexane-trans-1,4-diyl)bis(2,2-dimethylpropanamide) 1, 1,1′-(cyclohexane-trans-1,4-diyl)bis(3-tert-butylurea) 2 and N 1 ,N 4-bis(tert-butylcarbamoyl)cyclohexane-trans-1,4-dicarboxamide 3. Based on a complete signal assignment of the 1D solid-state MAS NMR spectra (1 H, 13 C, 15 N) employing 2D HETCOR experiments and a quantitative evaluation of the corresponding resonances, the content of the asymmetric unit was determined to one half of a molecule. Probing the molecular configuration with 1 H-1 H double-quantum experiments revealed an intramolecular hydrogen bond for compound 3 while 1 and 2 form exclusively intermolecular H-bonds. Ab initio structure solutions applying real space methods with an included close-contact penalty were carried out for all compounds. The following Rietveld refinements led to excellent wR p-values between 2.5% and 4.1%. Compounds 1 and 2 crystallise isostructurally in the monoclinic space group P2 1 /c exhibiting a pseudo-biaxial hydrogen bond motif. 3 crystallises in the triclinic space group P1 with intermolecular head-to-tail hydrogen bonds connecting the molecules to one-dimensional ribbons. Nevertheless, all compounds grow in a sheet-like morphology with lateral dimensions of several hundred micrometres indicating a fast growth in two dimensions along two of the crystal axes. Since all three molecules possess inversion symmetry cancelling the molecular dipole moment the growth mechanism itself has to be dominantly driven by the formation of hydrogen bond networks.

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N-[4-(2,2-Dimethylpropionylamino)phenyl]-2,2-dimethylpropionamide

Abstract: In the title compound, C16H24N2O8, the molecule is centrosymmetric. The crystal packing is stabilized by intermolecular N—H⋯O hydrogen bonds.

Cited by 3 publications

References 3 publications

N,N′-(p-Phenylene)bis(2,2,2-trifluoroacetamide)

N,N′-(p-Phenylene)bis(2,2,2-trifluoroacetamide)

Crystal Engineering of Supramolecular 1,4‐Benzene Bisamides by Side‐Chain Modification – Towards Tuneable Anisotropic Morphologies and Surfaces

NMR-crystallographic study of two-dimensionally self-assembled cyclohexane-based low-molecular-mass organic compounds

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N-[4-(2,2-Dimethylpropionylamino)phenyl]-2,2-dimethylpropionamide

Abstract: In the title compound, C16H24N2O8, the mol­ecule is centrosymmetric. The crystal packing is stabilized by inter­molecular N—H⋯O hydrogen bonds.

Cited by 3 publications

References 3 publications

N,N′-(p-Phenylene)bis(2,2,2-trifluoroacetamide)

N,N′-(p-Phenylene)bis(2,2,2-trifluoroacetamide)

Crystal Engineering of Supramolecular 1,4‐Benzene Bisamides by Side‐Chain Modification – Towards Tuneable Anisotropic Morphologies and Surfaces

NMR-crystallographic study of two-dimensionally self-assembled cyclohexane-based low-molecular-mass organic compounds

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Product

Resources

About

Abstract: In the title compound, C16H24N2O8, the molecule is centrosymmetric. The crystal packing is stabilized by intermolecular N—H⋯O hydrogen bonds.