Electronic Supplementary Material (ESI) for CrystEngComm This journal is © The Royal Society of Chemistry 2011
The solvates of sulfamerazine: Structural,
thermochemical,
and
desolvation studies Srinivasulu Aitipamula,*,a Pui Shan Chow,a and Reginald B.H. Tan*,a,b a
Institute of Chemical and Engineering Sciences, A*STAR (Agency for Science, Technology
and Research), 1, Pesek Road, Jurong Island, Singapore, 627833. Tel: (65) 6796 3858, Fax: (65) 6316 6183. Email:
[email protected]
b
Department of Chemical & Biomolecular Engineering, National University of Singapore, 4
Engineering Drive 4, Singapore 117576. Email:
[email protected]
Electronic Supplementary Information (10 Pages)
Contents Figs. S1
ORTEP diagrams
Figs. S2-S4
Packing diagrams of crystal structures of the SMZ polymorphs.
Figs. S5-S6
Comparison of the PXRD patterns of the samples obtained in the desolvation experiments
Table S1
List of CSD Refcodes of sulfonamide drug hydrates and their packing motifs.
Table S2
List of CSD Refcodes of sulfonamide drug hydrates and their packing motifs. List of CSD Refcodes found in the CSD analysis
Table S3
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Electronic Supplementary Material (ESI) for CrystEngComm This journal is © The Royal Society of Chemistry 2011
SMZ-Dioxane (1:0.5)
SMZ-Dioxane (1:1)
SMZ-DMA
SMZ-DMF
SMZ-CP
SMZ-3PC
Fig. S1 ORTEP diagrams of crystal structures of the SMZ solvates. Thermal ellipsoids are drawn at 50 % probability.
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Fig. S2 A distorted hexagonal network in the crystal structure of SMZ Form I.
Fig. S3 A ladder network in the crystal structure of SMZ Form II.
Fig. S4 A ladder network in the crystal structure of SMZ Form III.
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Fig. S5 Comparison of the PXRD patterns of the samples obtained in the desolvation experiments on the solvates of SMZ at ambient conditions.
Fig. S6 Comparison of the PXRD patterns of the samples obtained in the desolvation experiments on the solvates of SMZ at 90 °C in a vacuum oven. Notice that all the solvates converted to Form I. 4
Electronic Supplementary Material (ESI) for CrystEngComm This journal is © The Royal Society of Chemistry 2011
Table S1. List of CSD Refcodes of sulfonamide drug solvates and their packing motifs. Solvates of sulfonamide drugs – 41 Refcode
Solvent
ADEDIX ADEFOF BABYIN BABYOT
GIMRUQ GIMSAX
Pyridine DMA Acetonitrile N-formyl piperidine Ethylacetate Pyridine Ethylacetate Aniline Acetonitrile Acetonitrile Caprylic acid 1,4-dioxane Ethyl methyl ketone Acetone DMF
Molar ratio Hydrogen bond (sulfonamide:solvent) network involving sulfonamide moleculesa 1:1 1D ladder 1:2 2D layer 1:1 2D bilayer 1:1 1D chain 1:1 2D layer 1:3 0D (not a dimer) 1:0.5 1D ladder 1:1 2D layer 1:1 1D chain 1:1 1D chain 1:1 0D dimer 1:0.25 0D dimer 1:0.5 1D chain 1:1 2D layer 1:1 3D channel
HEZNEF HEZNIJ HEZNOP HOMZIS IRILOK IRILUQ JENGIS
1-Butanol 1-Pentanol 1,4-Dioxane Methanol Methanol Ethanol Methanol
1:1 1:1 1:1 1:0.5 1:1 1:1 2:3
KEFGAD
Acetone
1:1
LIWMIN LOWKOX MAJQOE MAJQUK
1,4-Dioxane Methanol Methanol Ethanol
1:1 1:1 1:1 1:1
BIXMIF BIZXEO BONROM CASMAL DAHNIJ DATTUN DIKCUW DIKDUX FAYGOC
1D chain 1D chain 1D chain 0D (not a dimer) 2D layer 2D layer 1D column mediated by malate ions Complex 3D structure 0D (not a dimer) 0D (not a dimer) 1D chain 1D chain 5
Remark
cocrystal cocrystal Salt of S-Malic acid
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MALVOL MAPPUP NIKROP NUQGOV ODATIX ODEFEJ PEHYEH
Dimethylsulfoxide Acetonitrile Dimethylsulfoxide Chloroform DMF Dimethylsulfoxide Tetrahydrofuan
1:1 1:1 1:2 1:1 1:1 1:1 1:2
1D chain 1D chain 1D chain 3D coordinates not available 2D layer 0D dimer 1D chain
PIWWAU RASSUZ VIDMUR VIDNEC WOMYAZ YABMIX YESKIR
Acetone Methanol DMA Dimethylsulfoxide Acetone Methanol N-methyl-2pyrrolidone
1:1 1:1 1:2 1:1 1:1 1:1 1:2
1D chain 2D layer 0D dimer 1D chain 1D chain 0D dimer 1D chain
a
cocrystal
Only the strong hydrogen bonds between the molecules of sulfonamide drugs are considered.
Table S2. List of CSD Refcodes of sulfonamide drug hydrates and their packing motifs. Hydrates of sulfonamide drugs – 27
Refcode
Molar ratio (sulfonamide:water) 1:1
Hydrogen bond network involving sulfonamide moleculesa
Remark
CIDYAP CITYEJ
1:2
No sulfonamide-sulfonamide hydrogen bonds. The sulfonamide molecules are connected through water molecules and generate a 3D structure No sulfonamide-sulfonamide 0D hydrogen bonds. 1D hydrogen bond ladder mediated by water molecules 2D layer mediated by water 0D tetramer molecules 3D coordinates not available
CUBKEQ
1:1
0D
ACIGEY
0D
1:2 AHUXOR 1:1
No sulfonamide-sulfonamide hydrogen bonds. 1D hydrogen bond
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ladder mediated by water molecules DAGGIC DICVOB
1:1 1:1
3D structure 1D chain
FEDTEO GUSHAD
1:1 1:0.5
2D sheet structure mediated by water molecules 3D structure Salt of citric acid. 3D coordinates not available
IRIMEB JEBNUZ KOCLUK LEPMOJ
1:1 1:1 1:1 1:1
3D structure 2D layer 1D chain 1D chain
1:1 MAJQIY
1D chain 1:1
MIVNIO01
0D (not a dimer)
QACQUH QOGHUQ
1:1 1:2
RIWLOY SOBZIM
1:1 1:1
SULAMH10 1:1 1:1
1D chain 0D
1:3
2D layer
1:1 1:1 1:1
1D chain 2D layer 0D
0.22:18.7
1D chain
0.5:9.2
1D chain
ZOWDUK BURXOC BURXUI a
Crystal structure contains water and ethanol. 3D structure mediated by water molecules A four component unit with 2 each molecules of sulfonamide and water
1D chain 3D structure norfloxacinium saccharinate mediated by water saccharin cocrystal molecules 2D layer cocrystal 3D coordinates not available
WECXEI WINJAE WODBEW WODBIA
Tetroxoprim sulfametrole cocrystal
No sulfonamide-sulfonamide hydrogen bonds. 2D hexagonal layer, each hexagon composed of 3 each molecules of sulfonamide and water Sodium salt
No sulfonamide-sulfonamide hydrogen bonds. 3D structure mediated by water molecules β-cyclodextrin inclusion complex. Crystal structure also contains ethanol molecule. β-cyclodextrin inclusion complex.
Only the strong hydrogen bonds between the molecules of sulfonamide drugs are considered.
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Table S3. List of CSD Refcodes of sulfonamide drug crystal structures. Hydrates of sulfonamide drugs - 27
Solvates of sulfonamide drugs - 41
Polymorphs of sulfonamide drugs - 25
ACIGEY AHUXOR CIDYAP CITYEJ CUBKEQ DAGGIC DICVOB FEDTEO GUSHAD IRIMEB JEBNUZ KOCLUK LEPMOJ MAJQIY
ADEDIX ADEFOF BABYIN BABYOT BIXMIF BIZXEO BONROM CASMAL DAHNIJ DATTUN DIKCUW DIKDUX FAYGOC GIMRUQ GIMSAX HEZNEF HEZNIJ HEZNOP HOMZIS IRILOK IRILUQ
ATDZSA BEDMIG BEWKUJ04 BIYSEH FOGVIG FURSEM HCSBTZ KUMCEB QQQAUG QQQBSS SAMPYM SLFNMA SLFNMB03
ACICAQ ACIGEY ADAGUI ADEDIX ADEFOF AHEMUV AHUXOR AJULUM AMAVIT ASUMEG ATDZSA BABYIN BABYOT BAGVUA BAPYIB BEBZIS BEDMIG BEGSEL
MIVNIO01 QACQUH QOGHUQ RIWLOY SOBZIM SULAMH10 WECXEI WINJAE WODBEW WODBIA ZOWDUK BURXOC BURXUI
JENGIZ KEFGAD LIWMIN LOWKOX MAJQOE MAJQUK MALVOL MAPPUP NIKROP NUQGOV ODATIX ODEFEJ PEHYEH PIWWAU RASSUZ VIDMUR VIDNEC WOMYAZ YABMIX YESKIR
SLFNMD10 SLFNMF SLFNMG SULDAZ03 SUTHAZ TOHBUN TORSEM VUHFIO WURMOM YUCCIJ ZZZAYP ZZZPUS
Sulfonamide drugs (including hydrates, solvates, and polymorphs) - 418 GARFEK MOKXOA SOJNEK VUQWIO GEHZAV MORJIM SOLSIW VUWBEV GEYSAE MORJUY SOTALC UKIFIE GIMRUQ MOWYON SOVDOW GIMSAX NADLIN SOVDUC GODRUM NAFVIA SUKHOV GODSAT NAWQOR SULAMD06 GODYED NAWQUX SULAMH10 GODYIH NEDSUK SULDAZ01 GUCMEW NERQEH SULPIA GUSHAD NIFKIX SULTAM HADTEL NIKCEQ SUTHAZ HAGMAD NIKROP SUVGUL HANFUY NITQOX TAHDUB HAWZEL NUNGIM TAMRUV HCSBTZ NUQGOV TAMXAG HEZNEF OBAWIX TAQVUD HEZNIJ OBAWOD TEDXAB
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BEWKUJ04 BILSEU BIVTAB BIXMIF BIXMUR BIYSEH BIZXEO BONROM BUDYEF BUDYUV BUNDHA10 CABCOX CABCUD CASMAL CAVGOV CEKHIJ CELNAJ CIDYAP CIHFAA CIRTIG CISKUL CITSON CITYEJ CIVBAK COMFOZ COXYOE COYVER COYVIV CUBKEQ CUQTEN CUZQOD DAGGIC DAHNIJ DATTUN DATWOK DAWRAU DEFZEU DEVLIZ DEVSON DEZQUU DIBBUL DICVOB DIKCIK DIKCOQ DIKCUW
HEZNOP HOLTUY HOMZIS HOQZET HORNEI HOSCAU HOTPAI HUHWAI IDIMOY IDUSUV IFAFAX IFODOX IFODUD INEDUA IRILOK IRILUQ IRIMEB IZEBEU IZEBIY JABJAY JABJEC JAGWAP JAQVAY JATLOF JATMEW JAWHOF JAYJUP JAZVEL JAZZOZ10 JEBNUZ JENGIS JIRKIE JIRKOK JIRLAX JIZGII JIZHEG JUWTUQ JUWWAZ KASXIM KATBEN KEFGAD KEFROC KEGXAW KENDOX KIFZUV
ODATIX ODEFEJ OFEHAJ OFIHIV OFIHOB OFIHUH PABJOR PECTAT PEHVEE PEHVII PEHWEF PEHYEH PEMYOV PEXYEX PIDVEE PILPEG PIWVIB PIWVUN PIWWAU POHYER PONZIC PUBZOB PUBZUH PYMSBZ QACQUH QASFIZ QAXSUD QEFQOH QIHPAY QIJZOY QIMBET QIMDIZ QIMDOF QIMDUL QIYMEQ QODGIA QOGHUQ QORSOG QOVQIC QOVQOI QQQAUD QQQAUG QQQBSS RALSED RASSUZ
TELWAI THTHXN TIKQEK TOHBUN TORSEM TUDTOB UDEWUV UFERED UNEZAO VAKPIH VAZTIA VEFXEJ VEKSEK VENLUV VIDMUR VIDNEC VIGVOW VITWIE VOHZIC VOKSET VOKXEY VOKXIC VONZIH VORBAF VUGMIT VUGMOZ VUHFIO VUXPEJ VUXPUZ WACJIT WASNOT WECXEI WENROX WEWVUQ WIKNAF WINJAE WINWUL WOBHUR WODBEW WODBIA WODBOG WOMYAZ WURBER WURMOM WUVSOW
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DIKDAD DIKDEH DIKDIL DIKDOR DIKDUX DIWSAE DIYJOL DOLJIX DONTOP DONTUV DUGPAW DUNLEE DUNXAL DUXYIE DUXYOK EDEZES EFOFAH ENIROI ETITEG EWUHAF01 EXOCUP FAXVAB FAXZIO FAYGOC FEDTEO FEYKIE FEYKOK FIDDAY FIKHEM FIKHIQ FIXNUV FOGVIG FOMZOX FORFEY FOWSUG FOWTAN FOZXUO FURSEM GAQTUO GAQVAW
KIKCUD KIKFEQ KIXJIL KOCLOE KOCLUK KOLHUP KOMVEO KONJAY KOQHAZ KOWZIF KUMCEB KUSVEZ LADTOZ LAWKUP LEPMOJ LICZOM LISCUL LIVPUB LIVQAI LIWBOJ LIWMIN LOCHUH LOCJAP LOWKOX LUJBOH MAJQIY MAJQOE MAJQUK MALVEB MALVOL MAPPUP MEHNUJ MEJTAX MENPEB MENPIF MENPUR MILFIW MINGOF MISMUX MISNAE MIVNIO01 MOCVEF
RAYLOT RETLEI RETLIM RETLOS REVJAE REZNOA RIQKOS RIWLOY RIYXED RIZKOB RUGFUU RUWCER SAMPYM SEBJAK SEBLEQ SEBPAQ SECDAF SEDZOQ SEQJUT SEQKAA SEQKEE SETSOA SEVHAD SFDMOX02 SIBDAI SIFFUJ SIMJEE SIQRAM SIVZIG SLFNMA SLFNMB03 SLFNMC10 SLFNMD01 SLFNMF SLFNMG SLFQUI SLFSMD10 SLFSXZ SOBJUO SOBZIM
XACVEC XETKUD XIGLAB XIYRUT XOXYAK XUDTIZ01 XUGNAO XUYTUG YABGUD YABMIX YAMPUY YANNEH YAWZIF YEKGUQ YESKIR YESMEO YEZJET YEZJIX YIBFEU YIGBEW YIGMUX YIHRUC YIZQAA YOCVOC YODGUU YOWTIN YUCCIJ YUKKUK ZEXWOO ZIKKAF ZOWDUK ZOYPEI ZOYPIM ZUWRIS ZZZAYP ZZZPUS BURXOC BURXUI FULHUQ NAJLOB QQQAUG09
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