A triclinic polymorph of miconazole

被引：1

作者：

Kaspiaruk, Hanna ^{[1
,2
]}

Checinska, Lilianna ^{[2
]}

机构：

[1] Univ Lodz, Doctoral Sch Exact & Nat Sci, Narutowicza 68, PL-90136 Lodz, Poland

[2] Univ Lodz, Fac Chem, Pomorska 163-165, PL-90236 Lodz, Poland

来源：

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS | 2024年 / 80卷

关键词：

miconazole; crystal structure; Hirshfeld surface; energy frameworks; MODEL ENERGIES;

D O I：

10.1107/S2056989024000276

中图分类号：

O7 [晶体学];

学科分类号：

0702 ; 070205 ; 0703 ; 080501 ;

摘要：

The crystal structure of the new triclinic polymorph of miconazole {MIC; C18H14Cl4N2O; systematic name: (RS)-1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole} is reported and compared with the monoclinic form of solvent-free miconazole previously reported [Kaspiaruk & Che. cinska (2022). Acta Cryst. C78, 343-350]. A comparison shows a different orientation of imidazole and one dichlorophenyl ring between polymorphic molecules. In the crystal structure of the title compound, only weak halogen bonds and C-H....(arene) interactions are found. Hirshfeld surface analysis and energy framework calculations complement the comparison of the two polymorphic forms of the miconazole drug.

引用

页码：196 / +

页数：11

共 24 条

[1]

BOTTER A A, 1971, Mykosen, V14, P187

[2] A combined experimental and theoretical study of miconazole salts and cocrystals: crystal structures, DFT computations, formation thermodynamics and solubility improvement [J].

Drozd, K. V. ;

Manin, A. N. ;

Voronin, A. P. ;

Boycov, D. E. ;

Churakov, A. V. ;

Perlovich, G. L. .

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2021, 23 (21) :12456-12470

[3] Simultaneous Improvement of Dissolution Behavior and Oral Bioavailability of Antifungal Miconazole via Cocrystal and Salt Formation [J].

Drozd, Ksenia, V ;

Manin, Alex N. ;

Boycov, Denis E. ;

Perlovich, German L. .

PHARMACEUTICS, 2022, 14 (05)

[4] The Cambridge Structural Database [J].

Groom, Colin R. ;

Bruno, Ian J. ;

Lightfoot, Matthew P. ;

Ward, Suzanna C. .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2016, 72 :171-179

[5] A comparison of three crystalline forms of miconazole: solvent-free, ethanol monosolvate and hemihydrate [J].

Kaspiaruk, Hanna ;

Checinska, Lilianna .

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2022, 78 :343-+

[6] Pharmaceutical solvate formation for the incorporation of the antimicrobial agent hydrogen peroxide [J].

Kersten, Kortney M. ;

Breen, Meghan E. ;

Mapp, Anna K. ;

Matzger, Adam J. .

CHEMICAL COMMUNICATIONS, 2018, 54 (67) :9286-9289

[7] CrystalExplorer model energies and energy frame-works: extension to metal coordination compounds, organic salts, solvates and open-shell systems [J].

Mackenzie, Campbell F. ;

Spackman, Peter R. ;

Jayatilaka, Dylan ;

Spackman, Mark A. .

IUCRJ, 2017, 4 :575-587

[8] Mercury 4.0: from visualization to analysis, design and prediction [J].

Macrae, Clare F. ;

Sovago, Ioana ;

Cottrell, Simon J. ;

Galek, Peter T. A. ;

McCabe, Patrick ;

Pidcock, Elna ;

Platings, Michael ;

Shields, Greg P. ;

Stevens, Joanna S. ;

Towler, Matthew ;

Wood, Peter A. .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2020, 53 :226-235

[9] New insights on the antibacterial efficacy of miconazole in vitro [J].

Nenoff, P. ;

Koch, D. ;

Krueger, C. ;

Drechsel, C. ;

Mayser, P. .

MYCOSES, 2017, 60 (08) :552-557

[10] Solvatomorphism in Miconazole: The Role of Weak C-H•••Cl Hydrogen Bonds and C-Cl•••Cl-C Halogen Interactions in Similarities and Differences in the Crystal Packing [J].

Panini, Piyush ;

Boel, Eline ;

Van Meervelt, Luc ;

Van den Mooter, Guy .

CRYSTAL GROWTH & DESIGN, 2022, 22 (04) :2703-2724

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