The crystal structures and melting point properties of isonicotinamide cocrystals with alkanediacids HO2C(CH2)n-2CO2H n=7-9

被引:28
作者
Thompson, Laura J. [1 ]
Voguri, Raja S. [1 ]
Male, Louise [1 ]
Tremayne, Maryjane [1 ]
机构
[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England
基金
英国工程与自然科学研究理事会;
关键词
MOLECULAR-COMPLEXES; ACIDS; ALTERNATION;
D O I
10.1039/c1ce05160a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The tunability of physiochemical properties of crystalline materials through controlled cocrystal formulation is an aim for both the pharmaceutical industry and crystal engineers. In this paper we report that the melting point alternation behaviour of odd and even alkanedicarboxylic acids is mimicked in a set of cocrystals in which isonicotinamide is combined in a 1:1 stoichiometry with pimelic acid, suberic acid and azelaic acid. All three structures contain hydrogen bonded chains of alternating acid and amide molecules between which acid-pyridine and acid-amide synthons are formed. Both isonicotinamide : pimelic acid and isonicotinamide : azelaic acid form structures in which the acid moiety adopts a twisted alkyl backbone conformation similar to that observed in the pure odd alkanediacid materials. The isonicotinamide : suberic acid cocrystal differs from the others reported here retaining both the elevated melting point and the planar acid conformation displayed by even alkanediacid materials in this series.
引用
收藏
页码:4188 / 4195
页数:8
相关论文
共 26 条
[1]   2-Acetaminopyridine:: A highly effective cocrystallizing agent [J].
Aakeröy, CB ;
Hussain, I ;
Desper, J .
CRYSTAL GROWTH & DESIGN, 2006, 6 (02) :474-480
[2]   Do polymorphic compounds make good cocrystallizing agents?: A structural case study that demonstrates the importance of synthon flexibility [J].
Aakeröy, CB ;
Beatty, AM ;
Helfrich, BA ;
Nieuwenhuyzen, M .
CRYSTAL GROWTH & DESIGN, 2003, 3 (02) :159-165
[3]   A high-yielding supramolecular reaction [J].
Aakeröy, CB ;
Beatty, AM ;
Helfrich, BA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (48) :14425-14432
[4]   Using Cocrystals To Systematically Modulate Aqueous Solubility and Melting Behavior of an Anticancer Drug [J].
Aakeroy, Christer B. ;
Forbes, Safiyyah ;
Desper, John .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (47) :17048-+
[5]   Crystal engineering of the composition of pharmaceutical phases.: Do pharmaceutical co-crystals represent a new path to improved medicines? [J].
Almarsson, Ö ;
Zaworotko, MJ .
CHEMICAL COMMUNICATIONS, 2004, (17) :1889-1896
[6]   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
[7]   Current directions in co-crystal growth [J].
Blagden, Nicholas ;
Berry, David J. ;
Parkin, Andrew ;
Javed, Hafsa ;
Ibrahim, Asim ;
Gavan, Pauline T. ;
De Matos, Luciana L. ;
Seaton, Colin C. .
NEW JOURNAL OF CHEMISTRY, 2008, 32 (10) :1659-1672
[8]   Inversion of the melting point alternation in n-alkyl carboxylic acids by co-crystallization with pyrazine [J].
Bond, AD .
CRYSTENGCOMM, 2006, 8 (04) :333-337
[9]   Mechanochemical preparation of hydrogen-bonded adducts between the diamine 1,4-diazabicyclo [2.2.2] octane and dicarboxylic acids of variable chain length: An x-ray diffraction and solid-state NMR study [J].
Braga, D ;
Maini, L ;
de Sanctis, G ;
Rubini, K ;
Grepioni, F ;
Chierotti, MR ;
Gobetto, R .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (22) :5538-5548
[10]  
Brandenburg K., 1997, DIAMOND VERSION 3 0