4-(Dodec-yloxy)benzonitrile

Area of Science:

• Crystallography and Molecular Structure
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Benzonitrile derivatives are important in various chemical applications.
• Understanding the solid-state behavior of organic molecules is crucial for materials science.
• Alkyl-benzene structures typically exhibit planar zigzag conformations in their aliphatic chains.

Purpose of the Study:

• To elucidate the crystal structure of the title compound, C(19)H(29)NO.
• To analyze the bond distances within the benzonitrile group.
• To investigate the conformational preferences of the aliphatic fragment and its packing in the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction analysis was employed to determine the molecular and crystal structure.
• Analysis of bond lengths (C-C and C-N) within the benzonitrile moiety.
• Identification and characterization of intermolecular interactions, including hydrogen bonds (C-H⋯O and C-H⋯N).

Main Results:

• The benzonitrile group exhibits characteristic C-C (1.445(2) Å) and C-N (1.157(2) Å) bond distances.
• The aliphatic fragment adopts a non-planar, bent zigzag conformation, deviating from the typical planar zigzag observed in similar compounds.
• Crystal packing reveals inversion dimers linked by C-H⋯O hydrogen bonds and a C-H⋯N interaction, forming a ripple-like motif along the a axis.

Conclusions:

• The title compound displays a unique bent zigzag conformation in its aliphatic chain, challenging typical structural expectations.
• Intermolecular hydrogen bonding plays a significant role in organizing the molecules within the crystal structure.
• The observed head-to-tail orientation of nitrile and aliphatic groups contributes to the formation of a distinct ripple-like motif.