Synthesis, characterization, crystal structure and Hirshfeld surface analysis of isobutyl 4-[4-(difluoromethoxy)phenyl]-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

被引:1
|
作者
Yildirim, Sema Ozturk [1 ,2 ]
Akkurt, Mehmet [3 ]
Cetin, Gokalp [4 ]
Simsek, Rahime [5 ]
Butcher, Ray J. [6 ]
Bhattarai, Ajaya [7 ]
机构
[1] Eskisehir Tech Univ, Dept Phys, Fac Sci, Yunus Emre Campus, TR-26470 Eskisehir, Turkiye
[2] Erciyes Univ, Dept Phys, Fac Sci, TR-38039 Kayseri, Turkiye
[3] Erciyes Univ, Dept Phys, Fac Sci, TR-38039 Kayseri, Turkiye
[4] Erzincan Binali Yildirim Univ, Dept Pharmaceut Chem, Fac Pharm, TR-24100 Erzincan, Turkiye
[5] Hacettepe Univ, Dept Pharmaceut Chem, Fac Pharm, TR-06100 Ankara, Turkiye
[6] Howard Univ, Dept Chem, Washington, DC 20059 USA
[7] M M A M C Tribhuvan Univ, Dept Chem, Biratnagar, Nepal
关键词
crystal structure; 1,4-dihydropyridine ring; cyclohexene ring; quinoline ring system; van der Waals interactions; Hirshfeld surface analysis;
D O I
10.1107/S2056989023009623
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
In the title compound, C24H29F2NO4, which crystallizes in the orthorhombic Pca2(1) space group with Z = 4, the 1,4-dihydropyridine ring adopts a distorted boat conformation, while the cyclohexene ring is in a distorted half-chair conformation. In the crystal, the molecules are linked by N-H center dot center dot center dot O and C-H center dot center dot center dot O interactions, forming supramolecular chains parallel to the a axis. These chains pack with C-H center dot center dot center dot pi interactions between them, forming layers parallel to the (010) plane. The cohesion of the crystal structure is ensured by van der Waals interactions between these layers. Hirshfeld surface analysis shows the major contributions to the crystal packing are from H center dot center dot center dot H (56.9%), F center dot center dot center dot H/H center dot center dot center dot F (15.7%), O center dot center dot center dot H/H center dot center dot center dot O (13.7%) and C center dot center dot center dot H/H center dot center dot center dot C (9.5%) contacts.
引用
收藏
页码:1132 / +
页数:11
相关论文
共 50 条
  • [41] Synthesis of 4-aryl-2,7,7-trimethyl-5-oxo-n-phenyl-1,4,5,6,7,8-hexahydroquinoline-3-carboxamides
    V. L. Gein
    M. I. Kazantseva
    A. A. Kurbatova
    M. I. Vahrin
    Chemistry of Heterocyclic Compounds, 2010, 46 : 629 - 630
  • [42] Ethyl 2,7,7-trimethyl-4-(1-methyl-1H-indol-3-yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
    Yildirim, Sema Ozturk
    Butcher, Ray J.
    Gunduz, Miyase Gozde
    El-Khouly, Ahmed
    Simsek, Rahime
    Safak, Cihat
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O40 - +
  • [43] Synthesis of 4-isobutyl-5-oxo-3-cyano-1,4,5,6,7,8-hexahydroquinoline-2-thiol and its alkylation
    Krivokolysko, SG
    Dyachenko, VD
    Litvinov, VP
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1999, (02): : 230 - 231
  • [44] N,N-Diethyl-2,6,6-trimethyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxamide
    Linden, A
    Safak, C
    Kismetli, E
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2002, 58 : o436 - o438
  • [45] Synthesis, structural characterization and density functional studies of ethyl 4-(biphenyl-4-yl)-2,6,6-trimethy1-5-oxo-1,4,5,6,7,8-updtte hexahydroquinoline-3-carboxylate A non-merohedral twinned structure
    Yidirim, Sema Ozturk
    Buyukmumcu, Zeki
    Butcher, Ray J.
    Cetin, Gokalp
    Simsek, Rahime
    Safak, Cihat
    JOURNAL OF MOLECULAR STRUCTURE, 2018, 1163 : 161 - 166
  • [46] Crystal structure of methyl 4-(4-isopropylphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylate, C23H29NO3
    Li, Da
    Zhou, Yan
    Zhao, Li
    Zhang, Hua
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2019, 234 (01): : 35 - 36
  • [47] Crystal structure and metabolic activity of 4-(thien-2-yl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethoxycarbonylphenylmethylester
    Mishnev, Anatoly
    Bisenieks, Egils
    Mandrika, Ilona
    Petrovska, Ramona
    Kalme, Zenta
    Bruvere, Manta
    Duburs, Gunars
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2018, 74 : 1577 - +
  • [48] Synthesis and calcium antagonistic activity of 2,6,6-trimethyl-3-carbomethoxy(ethoxy)-4-aryl-1,4,5,6,7,8-hexahydroquinoline derivatives
    Simsek, R
    Ismailoglu, UB
    Safak, C
    Sahin-Erdemli, I
    FARMACO, 2000, 55 (11-12): : 665 - 668
  • [49] Synthesis and crystal structure of 2,7,7-trimethyl-3-ethoxycarbonyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline under microwave irradiation
    Tu, SJ
    Yu, CX
    Liu, XH
    Yao, CS
    Liu, F
    Gao, Y
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2002, 21 (01) : 99 - 102
  • [50] Crystal structure of methyl 4-(3-phenoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydro quinoline-3-carboxylate, C26H27NO4
    Gou, Wei
    Chen, Gang
    Chen, Wei-Yong
    Li, Wen-Jun
    Feng, Jing
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2019, 234 (01): : 53 - 54