Home The crystal structure of R-2′-amino-N-methyl-N-(1-phenylethyl)-[1,1′-biphenyl]-4-carboxamide, C22H22N2O
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The crystal structure of R-2′-amino-N-methyl-N-(1-phenylethyl)-[1,1′-biphenyl]-4-carboxamide, C22H22N2O

  • Yi Yao , Jia-Jun Liang and Hai-Ping Wang ORCID logo EMAIL logo
Published/Copyright: May 22, 2025

Abstract

C22H22N2O, orthorhombic, P212121, a = 7.09830(10) Å, b = 13.8691(2) Å, c = 18.1492(3) Å, V = 1786.76(5) Å3, Z = 4, R gt(F) = 0.0386, wR ref(F 2) = 0.1078, T = 300 K.

CCDC no.: 2422815

The molecular structure is shown in the figure. Table 1 contains the crystallographic data and the list of the atoms including atomic coordinates and displacement parameters can be found in the cif-file attached to this article.

Table 1:

Data collection and handling.

Crystal: Clear light colourless needle
Size: 0.10 × 0.05 × 0.03 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 0.59 mm−1
Diffractometer, scan mode: Rigaku Synergy, ω scans
θ max, completeness: 66.6°, 100 %
N(hkl)measured, N(hkl)unique, R int: 11195, 3162, 0.028
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 3,009
N(param)refined: 235
Programs: Rigaku, 1 SHELX, 2 Olex2 3

1 Source of materials

All chemicals were purchased from commercial sources and used as received without further purification. R-2′-amino-N-methyl-N-(1-phenylethyl)-[1,1′-biphenyl]-4-carboxamide was prepared by the Suzuki reaction between 2-aminophenylboronic acid and R-4-bromo-N-methyl-N-(1-phenylethyl)benzamide. A solution of R-2′-amino-N-methyl-N-(1-phenylethyl)-[1,1′-biphenyl]-4-carboxamide (0.01 mmol) in acetonitrile (5 mL). After filtration, slow diffusion of diethyl ether into the filtrate over 72 h afforded needle colourless crystals.

2 Experimental details

SHELXL 2 refinement package were employed to refine the crystal structure. The Olex2 3 was used to visualize the crystal structure. All hydrogen atoms were placed in idealized positions. Their U iso values were set to 1.2U eq of the parent atoms.

3 Comment

In the past thirty years, chiral research has become a hot topic in interdisciplinary fields such as chemistry, biology, physics, and materials science. 4 , 5 Chiral amine compounds are widely present in drug molecules, agrochemicals and functional materials. 6 , 7 Recently, chiral amide compounds are widely studied in the field of chiral luminescent materials due to their rich supramolecular interactions and photophysical properties. 8 , 9 , 10

The title compound is shown in the figure. The presence of the amino group in the side chain causes the dihedral angle between the two benzene rings to be 57.990°. The dihedral angle between the benzene ring connected to the chiral carbon atom C15 and the benzene ring with the amino group in the side chain is 96.29°. The C–N bond lengths range between 1.340(3)–1.459(3) Å, while the C–O bond length is 1.229(3) Å. The C–N–C bond angles range between 116.96(19)°–123.60(19)°. The O–C–N bond angle is 121.7(2)°. The O–C–C bond angle is 119.0(2)°. These values were close to those reported for related compounds. 11 , 12 All C–C and C–N bond lengths and angles are in the expected range.


Corresponding author: Hai-Ping Wang, Jiangmen Key Laboratory of Synthetic Chemistry and Cleaner Production, School of Environmental and Chemical Engineering, Wuyi University, Jiangmen, Guangdong, 529020, P.R. China; and Guangdong Laboratory of Chemistry and Fine Chemical Industry Jieyang Center, Jieyang, Guangdong, 515200, P.R. China, E-mail:

Acknowledgments

We gratefully acknowledge support by the NSFC of China (21703291), the NSF of Guangdong Province (2017A030310258), the Education Department of Guangdong Province (2022ZDJS027) and Jiangmen Municipal Science and Technology Bureau (Jiangke 2020-135, Jiangke 2021-76).

  1. Conflict of interest: The authors declare no conflicts of interest regarding this article.

  2. Research funding: NSFC of China (21703291), the NSF of Guangdong Province (2017A030310258), the Education Department of Guangdong Province (2022ZDJS027) and Jiangmen Municipal Science and Technology Bureau (Jiangke 2020-135, Jiangke 2021-76).

  3. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

References

1. Meyer, M.; Paciorek, W.; Kowalski, A.; Muszynski, A.; Wisniewski, A.; Pol, M.; Przewozniczek, M.; Stec, P.; Bujnik, D.; Kulza, H.; Grzesczyk, M.; Kuna, T.; Serwata, L.; Prochniak, G.; Piotrowski, W.; Antkowiak, M.; Jasiak, R.; Idzi, M.; Yoshida, H.; Hendrixson, T.; Archeson, C.; Wodziczko, T.; Jasnowski, M.; Ciesla, M.; Kapral, P.; Nawrocki, M.; Lasek, K.; Kempski, K.; Stepa, B.; Zarzecka, A. CrysAlisPRO Software System, Version 171.42.94a; Rigaku Oxford Diffraction, Rigaku Corporation: Wroclaw, 2023.Search in Google Scholar

2. Sheldrick, G. M. Crystal Structure Refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8, https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

3. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: A Complete Structure Solution, Refinement and Analysis Program. J. Appl. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar

4. Bonner, W. A. Origins of Molecular Chirality (Statistical, Physical and Biotic Theories on Molecular Chirality Origin, Considering Catalytic Processes and Asymmetric Processes with Circularly Polarized Light). Exobiology 1972, 170–234.Search in Google Scholar

5. Bode, M.; Heide, M.; Von, K.; Ferriani, P.; Heinze, S.; Bihlmayer, G.; Kubetzka, A.; Pietzsch, O.; Blügel, S.; Wiesendanger, R. Chiral Magnetic Order at Surfaces Driven by Inversion Asymmetry. Nature 2007, 447, 190–193; https://doi.org/10.1038/nature05802.Search in Google Scholar PubMed

6. Caglioti, L.; Micskei, K.; Pályi, G. First Molecules, Biological Chirality, Origin(s) of Life. Chirality 2011, 23, 65–68; https://doi.org/10.1002/chir.20796.Search in Google Scholar PubMed

7. Katsonis, N.; Lacaze, E.; Ferrarini, A. Controlling Chirality with Helix Inversion in Cholesteric Liquid Crystals. J. Mater. Chem. 2012, 22, 7088–7097; https://doi.org/10.1039/c2jm15962g.Search in Google Scholar

8. Dan, L.; Yanyan, Z.; Yuan, Z.; Hongfeng, L.; Peng, C.; Wenbin, S.; Gao, T.; Yan, P. Chiral Binapo-controlled Diastereoselective Self-assembly and Circularly Polarized Luminescence in Triple-Stranded Europium(III) Podates. Inorg. Chem. 2018, 57; https://doi.org/10.1021/acs.inorgchem.8b00986.Search in Google Scholar PubMed

9. Li, M.; Zhang, C.; Fang, L.; Shi, L.; Tang, Z.; Lu, H. Y.; Chen, C. F. Chiral Nanoparticles with Full-Color and White Cpl Properties Based on Optically Stable Helical Aromatic Imide Enantiomers. ACS Appl. Mater. Interfaces 2018, 10, 8225–8230; https://doi.org/10.1021/acsami.8b00341.Search in Google Scholar PubMed

10. Duan, H.; Li, S.; Zhao, J.; Li, J. Nanocellulose-Induced Helical Assembled Films of a Coil Polymer with Multistimuli Response for Circularly Polarized Luminescent Security Materials. Chem. Eng. J. 2024, 483, 149130; https://doi.org/10.1016/j.cej.2024.149130.Search in Google Scholar

11. Ng, J. C. Y.; Liu, J.; Su, H.; Hong, Y.; Li, H.; Lam, J. W. Y.; Wong, K. S.; Tang, B. Z. Complexation-Induced Circular Dichroism and Circularly Polarised Luminescence of an Aggregation-Induced Emission Luminogen. J. Mater. Chem. C 2014, 2, 78; https://doi.org/10.1039/c3tc31633e.Search in Google Scholar

12. Natarajan, A.; Mague, J. T.; Ramamurthy, V. Designed Molecular Propellers Based on Tetraarylterephthalamide and Their Chiroptical Properties Induced by Biased Helicity through Transmission of Point Chirality. Cryst. Growth Des. 2005, 5, 2348; https://doi.org/10.1021/cg0501175.Search in Google Scholar

Received: 2025-03-14
Accepted: 2025-04-29
Published Online: 2025-05-22
Published in Print: 2025-08-26

© 2025 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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