Ethenzamide-gentisic acid-acetic acid (2/1/1)

被引:11
作者
Aitipamula, Srinivasulu [1 ]
Chow, Pui Shan [1 ]
Tan, Reginald B. H. [1 ,2 ]
机构
[1] Agcy Sci Technol & Res, Inst Chem & Engn Sci, Jurong Isl 627833, Singapore
[2] Natl Univ Singapore, Dept Chem & Biomol Engn, Singapore 117576, Singapore
来源
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE | 2010年 / 66卷
关键词
PHARMACEUTICAL PHASES; CARBAMAZEPINE;
D O I
10.1107/S1600536810012407
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
In the title co-crystal solvate, 2-ethoxybenzamide-2,5-dihydroxybenzoic acid-ethanoic acid (2/1/1), 2C(9)H(11)NO(2)center dot C7H6O4 center dot C2H4O2, two nonsteroidal anti-inflammatory drugs, ethenzamide (systematic name: 2-ethoxybenzamide) and gentisic acid (systematic name: 2,5-dihydroxybenzoic acid), together with acetic acid (systematic name: ethanoic acid) form a four-component molecular assembly held together by N-H center dot center dot center dot O and O-H center dot center dot center dot O hydrogen bonds. This assembly features two symmetry-independent molecules of ethenzamide, forming supramolecular acid-amide heterosynthons with gentisic acid and acetic acid. These heterosynthons involve quite strong O-H center dot center dot center dot O [O center dot center dot center dot O = 2.5446 (15) and 2.5327 (15) angstrom] and less strong N-H center dot center dot center dot O [N center dot center dot center dot O = 2.9550 (17) and 2.9542 (17) angstrom] hydrogen bonds. The overall crystal packing features several C-H center dot center dot center dot O and pi-pi stacking interactions [centroid-centroid distance = 3.7792 (11) angstrom].
引用
收藏
页码:O1045 / U1540
页数:14
相关论文
共 15 条
[1]   Trimorphs of a pharmaceutical cocrystal involving two active pharmaceutical ingredients: potential relevance to combination drugs [J].
Aitipamula, Srinivasulu ;
Chow, Pui Shan ;
Tan, Reginald B. H. .
CRYSTENGCOMM, 2009, 11 (09) :1823-1827
[2]   Dimorphs of a 1:1 cocrystal of ethenzamide and saccharin: solid-state grinding methods result in metastable polymorph [J].
Aitipamula, Srinivasulu ;
Chow, Pui Shan ;
Tan, Reginald B. H. .
CRYSTENGCOMM, 2009, 11 (05) :889-895
[3]   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
[4]  
[Anonymous], 2008, CRYSTALCLEAR
[5]  
Barbour L.J., 2001, J SUPRAMOL CHEM, V1, P189, DOI [DOI 10.1016/S1472-7862(02)00030-8, 10.1016/S1472-7862(02)00030-8]
[6]   AN EMPIRICAL CORRECTION FOR ABSORPTION ANISOTROPY [J].
BLESSING, RH .
ACTA CRYSTALLOGRAPHICA SECTION A, 1995, 51 :33-38
[7]  
DESIRAJU GR, 1999, IUCR MONOGRAPHS CRYS, V9, P13
[8]   Crystal engineering of the composition of pharmaceutical phases:: Multiple-component crystalline solids involving carbamazepine [J].
Fleischman, SG ;
Kuduva, SS ;
McMahon, JA ;
Moulton, B ;
Walsh, RDB ;
Rodríguez-Hornedo, N ;
Zaworotko, MJ .
CRYSTAL GROWTH & DESIGN, 2003, 3 (06) :909-919
[9]  
Hirasawa N, 1999, CHEM PHARM BULL, V47, P417, DOI 10.1248/cpb.47.417
[10]   GENTISIC ACID - AN ASPIRIN METABOLITE WITH MULTIPLE EFFECTS ON HUMAN-BLOOD POLYMORPHONUCLEAR LEUKOCYTES [J].
LORICO, A ;
MASTURZO, P ;
VILLA, S ;
SALMONA, M ;
SEMERARO, N ;
DEGAETANO, G .
BIOCHEMICAL PHARMACOLOGY, 1986, 35 (14) :2443-2445