Crystal structures and Hirshfeld surface analyses of methyl 4-{2,2-dichloro-1-[(E)-phenyldiazenyl]ethenyl}benzoate, methyl 4-{2,2-dichloro-1-[(E)-(4-methylphenyl)diazenyl]ethenyl}benzoate and methyl 4-{2,2-dichloro-1-[(E)-(3,4-dimethylphenyl)diazenyl]ethenyl}benzoate

Crystal structures and Hirshfeld surface analyses of methyl 4-{2,2-dichloro-1-[(E)-phenyldiazenyl]ethenyl}benzoate, methyl 4-{2,2-dichloro-1-[(E)-(4-methylphenyl)diazenyl]ethenyl}benzoate and methyl 4-{2,2-dichloro-1-[(E)-(3,4-dimethylphenyl)diazenyl]ethenyl}benzoate Full article

Journal

Acta Crystallographica Section E: Crystallographic Communications
ISSN: 2056-9890

Output data

Year: 2024, Volume: 80, Number: 2, Pages: 184-190 Pages count : 7 DOI: 10.1107/s2056989024000732

Authors

Shikhaliyev Namiq Q. ¹ , İbrahimova Shafiga A. ¹ , Atakishiyeva Gulnar T. ¹ , Ahmedova Nigar E. ¹ , Babayeva Gulnara V. ^2,1 , Khrustalev Victor N. ^3,4 , Atioğlu Zeliha ⁵ , Akkurt Mehmet ⁶ , Bhattarai Ajaya ⁷

Affiliations

1	Organic Chemistry Department, Baku State University, Z. Khalilov str. 23, AZ 1148 Baku, Azerbaijan
2	Department of Analytical and Organic Chemistry, Azerbaijan State Pedagogical University, Uzeyir Hajibeyli str., 68, Baku, Azerbaijan
3	N. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation
4	Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St. 6, Moscow, 117198, Russian Federation
5	Department of Aircraft Electrics and Electronics, School of Applied Sciences, Cappadocia University, Mustafapaşa, 50420 Ürgüp, Nevşehir, Türkiye
6	Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye
7	Department of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal

The crystal structures and Hirshfeld surface analyses of three similar azo compounds are reported. Methyl 4-{2,2-dichloro-1-[(E)-phenyldiazenyl]ethenyl}benzoate, C16H12Cl2N2O2, (I), and methyl 4-{2,2-dichloro-1-[(E)-(4-methylphenyl)diazenyl]ethenyl}benzoate, C17H14Cl2N2O2, (II), crystallize in the space group P21/c with Z = 4, and methyl 4-{2,2-dichloro-1-[(E)-(3,4-dimethylphenyl)diazenyl]ethenyl}benzoate, C18H16Cl2N2O2, (III), in the space group P[\overline{1}] with Z = 2. In the crystal of (I), molecules are linked by C—H⋯N hydrogen bonds, forming chains with C(6) motifs parallel to the b axis. Short intermolecular Cl⋯O contacts of 2.8421 (16) Å and weak van der Waals interactions between these chains stabilize the crystal structure. In (II), molecules are linked by C—H⋯O hydrogen bonds and C—Cl⋯π interactions, forming layers parallel to (010). Weak van der Waals interactions between these layers consolidate the molecular packing. In (III), molecules are linked by C—H⋯π and C—Cl⋯π interactions forming chains parallel to [011]. Furthermore, these chains are connected by C—Cl⋯π interactions parallel to the a axis, forming (0[\overline{1}]1) layers. The stability of the molecular packing is ensured by van der Waals forces between these layers.

Shikhaliyev N.Q. , İbrahimova S.A. , Atakishiyeva G.T. , Ahmedova N.E. , Babayeva G.V. , Khrustalev V.N. , Atioğlu Z. , Akkurt M. , Bhattarai A.
Crystal structures and Hirshfeld surface analyses of methyl 4-{2,2-dichloro-1-[(E)-phenyldiazenyl]ethenyl}benzoate, methyl 4-{2,2-dichloro-1-[(E)-(4-methylphenyl)diazenyl]ethenyl}benzoate and methyl 4-{2,2-dichloro-1-[(E)-(3,4-dimethylphenyl)diazenyl]ethenyl}benzoate
Acta Crystallographica Section E: Crystallographic Communications. 2024. V.80. N2. P.184-190. DOI: 10.1107/s2056989024000732 WOS Scopus OpenAlex

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Scopus:	2-s2.0-85184596854
OpenAlex:	W4391261932

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