Analysis of intermolecular interactions involving halogens in substituted benzanilides

被引:13
作者
Chopra, D [1 ]
Row, TNG [1 ]
机构
[1] Indian Inst Sci, Solid State & Struct Chem Unit, Bangalore 560012, Karnataka, India
关键词
weak interactions; hydrogen bonds; polymorphism; molecular conformation;
D O I
10.1016/j.molstruc.2004.03.011
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Crystal structures of halogen-substituted benzanilides have been analyzed in terms of weak interactions involving halogens. The four compounds namely 3-fluoro-N-(3-hydroxyphenyl)benzamide, 3-chloro-N-(3-hydroxyphenyl)benzamide, 3-fluoro-N-(4-methylphenyl)benzamide and 3-chloro-N-(4-methylphenyl)benzamide crystallize in monoclinic symmetry. The packing modes in the crystalline lattice generate motifs via N-(HO)-O-... and O-(HO)-O-... hydrogen bonds in structures 1 and 2 and via N-(HO)-O-... hydrogen bond, weak C-H... F and (ClCl)-Cl-... interactions in structures 3 and 4. These structures when compared with the polymorphs of benzanilide show no orientational disorder and depict subtle conformational changes, which are directed by both strong hydrogen bonds and weak interactions involving halogens. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:133 / 141
页数:9
相关论文
共 39 条
[1]   Crystal engineering: Strategies and architectures [J].
Aakeroy, CB .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1997, 53 :569-586
[2]   COMPLETION AND REFINEMENT OF CRYSTAL-STRUCTURES WITH SIR92 [J].
ALTOMARE, A ;
CASCARANO, G ;
GIACOVAZZO, C ;
GUAGLIARDI, A .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1993, 26 (pt 3) :343-350
[3]   FROM SOLID-STATE STRUCTURES AND SUPERSTRUCTURES TO SELF-ASSEMBLY PROCESSES [J].
AMABILINO, DB ;
STODDART, JF ;
WILLIAMS, DJ .
CHEMISTRY OF MATERIALS, 1994, 6 (08) :1159-1167
[4]   PATTERNS IN HYDROGEN BONDING - FUNCTIONALITY AND GRAPH SET ANALYSIS IN CRYSTALS [J].
BERNSTEIN, J ;
DAVIS, RE ;
SHIMONI, L ;
CHANG, NL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (15) :1555-1573
[5]   Salts of maleic and fumaric acids with organic polyamines: comparison of isomeric acids as building blocks in supramolecular chemistry [J].
Bowes, KF ;
Ferguson, G ;
Lough, AJ ;
Glidewell, C .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2003, 59 :100-117
[6]  
BRUKER, 1998, SMART SAINT SADABS X
[7]   Weak interactions involving organic fluorine: a comparative study of the crystal packing in substituted isoquinolines [J].
Choudhury, AR ;
Urs, UK ;
Row, TNG ;
Nagarajan, K .
JOURNAL OF MOLECULAR STRUCTURE, 2002, 605 (01) :71-77
[8]  
Desiraju G. R., 1989, DESIGN ORGANIC SOLID
[9]   THE C-H...O HYDROGEN-BOND IN CRYSTALS - WHAT IS IT [J].
DESIRAJU, GR .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (10) :290-296
[10]   THE NATURE OF HALOGEN ... HALOGEN INTERACTIONS - ARE SHORT HALOGEN CONTACTS DUE TO SPECIFIC ATTRACTIVE FORCES OR DUE TO CLOSE PACKING OF NONSPHERICAL ATOMS [J].
DESIRAJU, GR ;
PARTHASARATHY, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8725-8726