Role of weak C-H• • •O and strong N-H• • •O intermolecular interactions on the high-symmetry molecular packing of trans-cyclohexane-1,4-dicarboxamude

被引：3
|
作者：
Garcia-Reyes, Fernando [1 ]
Fantoni, Adolfo C. [1 ]
Baron, Maximo [2 ]
Romano, Rosana M. [3 ]
Punte, Graciela M. [1 ]
Echeverria, Gustavo A. [1 ,4 ]
机构：
[1] Univ Nacl La Plata, Fac Ciencias Exactas, Dept Fis, IFLP,CONICET,CCT La Plata, RA-1900 La Plata, Buenos Aires, Argentina
[2] Univ Belgrano, Fac Ciencias Exactas & Nat, Villanueva 1324, RA-1426 Buenos Aires, DF, Argentina
[3] Univ Nacl La Plata, Dept Quim, Fac Ciencias Exactas, CEQUINOR,UNLP,CONICET,CCT La Plata, RA-1900 La Plata, Buenos Aires, Argentina
[4] Univ Nacl La Plata, Fac Ingn, RA-1900 La Plata, Buenos Aires, Argentina
来源：
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY | 2018年 / 74卷
关键词：
crystal structure; ab initio calculations; hydrogen bonds; carboxamide; IR spectroscopy; Raman spectroscopy; TRANS-1,4-SUBSTITUTED CYCLOHEXANES; CRYSTAL-STRUCTURES; PRIMARY AMIDES; DENSITY; MODES; ACID;
D O I：
10.1107/S2053229618011750
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An unpredicted fourfold screw N-H center dot center dot center dot O hydrogen bond C(4) motif in a primary dicarboxamide (trans-cyclohexane-1,4-dicarboxamide, C8H14N2O2) was investigated by single-crystal X-ray diffraction and IR and Raman spectroscopies. Electron-density topology and intermolecular energy analyses determined from ab initio calculations were employed to examine the influence of weak C-H center dot center dot center dot O hydrogen-bond interactions on the peculiar arrangement of molecules in the tetragonal P4(3)2(1)2 space group. In addition, the way in which the co-operative effects of those weak bonds might modify their relative influence on molecular packing was estimated from cluster calculations. Based on the results, a structural model is proposed which helps to rationalize the unusual fourfold screw molecular arrangement.
引用
收藏
页码：1068 / +
页数：15
相关论文
共 50 条
  • [41] Tetramidocavitand: strong anion receptor by well-organized four -(C=O)N-H•••X- interactions
    Jung, Nak Shin
    Lee, Jaeok
    Choi, Sang Beom
    Kim, Jaheon
    Paek, Kyungsoo
    TETRAHEDRON LETTERS, 2010, 51 (09) : 1291 - 1293
  • [42] A cocrystal of L-ascorbic acid with picolinic acid: the role of O-H•••O, N-H•••O and C-H•••O hydrogen bonds and L-ascorbic acid conformation in structure stabilization
    Evtushenko, Diana N.
    Arkhipov, Sergey G.
    Fateev, Alexander, V
    Izaak, Tatyana I.
    Egorova, Lidia A.
    Skorik, Nina A.
    Vodyankina, Olga V.
    Boldyreva, Elena, V
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2020, 76 : 967 - 978
  • [43] Intermolecular N-H [midline ellipsis] N and C-H [midline ellipsis] O interactions form one-dimensional chains comprising the two independent molecules of N,N prime -dicyclohexyl-N-nicotinoylurea
    School of Chemical Sciences, Dublin City University, Dublin 9, Ireland
    Acta Crystallogr Sect C Cryst Struct Commun, 9 (1607-1610):
  • [44] 2,2′-Biphenol-1,4-diazabicyclo[2.2.2]octane (2/1), a three-dimensional framework built from O-H•••O, O•••N, N-H•••O and C-H•••π(arene) hydrogen bonds
    Glidewell, C
    Ferguson, G
    Gregson, RM
    Lough, AJ
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1999, 55 : 2136 - 2140
  • [45] Structures of arylaldehyde 7-chloroquinoline-4-hydrazones: supramolecular arrangements derived from N-H•••N, C-H•••X (X = N, O, or π) and π•••π interactions
    Howie, R. Alan
    de Souza, Marcus V. N.
    Ferreira, Marcelle de Lima
    Kaiser, Carlos R.
    Wardell, James L.
    Wardell, Solange M. S. V.
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-CRYSTALLINE MATERIALS, 2010, 225 (10): : 440 - 447
  • [46] Macrocyclization and molecular interlocking via Mitsunobu alkylation:: Highlighting the role of C-H•••O interactions in templating
    Hansen, JG
    Feeder, N
    Hamilton, DG
    Gunter, MJ
    Becher, J
    Sanders, JKM
    ORGANIC LETTERS, 2000, 2 (04) : 449 - 452
  • [47] Influence of classical N-H ... O and C-H ... O hydrogen bonding interactions on 2-amino-5-methylpyridinium hydrogen succinate crystal: experimental and theoretical perspectives ...
    Nithya, S.
    Chandar Shekar, B.
    Aranganayagam, K. R.
    Boopathi, K.
    MATERIALS RESEARCH EXPRESS, 2019, 6 (12)
  • [48] On the interaction between N-heterocyclic carbenes and organic acids:: Structural authentication of the first N-H•••C hydrogen bond and remarkably short C-H•••O interactions
    Cowan, JA
    Clyburne, JAC
    Davidson, MG
    Harris, RLW
    Howard, JAK
    Küpper, P
    Leech, MA
    Richards, SP
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (08) : 1432 - 1434
  • [49] 2,4-dinitrophenyl 4-toluenesulfonate:: molecular aggregation through weak C-H• • •O interactions
    Vembu, N
    Nallu, M
    Garrison, J
    Youngs, WJ
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2003, 59 : O378 - O380
  • [50] Weak O-Assistance Outcompeting Strong N,N-Bidentate Directing Groups in Copper Catalyzed C-H Chalcogenation
    Cera, Gianpiero
    Ackermann, Lutz
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (25) : 8475 - 8478
12345