supplementary information (si-1 to si-8) si-1: preparation of … · 2013. 5. 14. · si-1:...
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Supplementary Information (SI-1 to SI-8)
SI-1: Preparation of molecular adducts (1a – 1f).
SI-2: Details of crystallographic analysis of the molecular adducts (1a – 1f).
SI-3: Preparation of phase-pure molecular adducts (1a – 1f).
SI-4: Crystallographic Table
SI-5: Hydrogen bond table
SI-6: DSC of various adducts (1a-1g)
SI-7: TGA of various adducts (1a-1f)
SI-8: Reference code of structures found in CSD containing Synthons 1, 2 and 3
Electronic Supplementary Material (ESI) for CrystEngCommThis journal is © The Royal Society of Chemistry 2013
SI-1: Preparation of molecular adducts (1a – 1f).
All the chemicals used in this study were obtained from aldrich and used as such without any
further purification. The solvents employed for the crystallization purpose were of spectroscopy grade
of highest available purity. Molecular adducts have been prepared by dissolving the triazine, 1, and
the corresponding carboxylic acid in a 1:1 ratio in a CH3OH solvent and slowly evaporating the
obtained solution. Single crystals were obtained over a period of 48 h in all the cases. In a typical
preparation, 0.0935 g (0.5 mmol) of 1 and 0.0830 g (0.5 mmol) of isophthalic acid were dissolved in
30 mL of CH3OH by gently warming on a water bath. The resultant solution was kept for evaporation
at ambient conditions by protecting the conical flask from external mechanical disturbances and
within 48 h, colourless and good quality crystals of 1f, were obtained that are suitable for studies by
single crystal X-ray diffraction methods.
SI-2: Details of crystallographic analysis of the molecular adducts (1a – 1f).
Good quality single crystals of 1a – 1f obtained by the procedure described above, have been chosen
by viewing under microscope and glued to a glass fibre using an adhesive to mount on a goniometer
of Bruker single crystal X-ray diffractometer equipped with APEX CCD detector. The data collections
were smooth in all the cases without any complications and all the crystals were found to be stable
throughout data collection period. The intensity data were processed using Bruker suite of
programmes,1 SAINT,
followed by absorption correction by SADABS.
1 The structures were solved by
using SHELXS and refined by least-square methods using SHELXL.1 All the non-hydrogen atoms
were refined by anisotropical methods and the hydrogen atoms were either refined or placed in the
calculated positions. All the structural refinements converged to good R-factors as listed in Table 1
and the intermolecular interactions were computed using PLATON software,2 and have been given in
Table 2. The packing diagrams were generated using Diamond, version 3.1e.3
SI-3: Preparation of phase-pure molecular adducts (1a – 1f).
The phase pure adducts were obtained by grinding 1 and various acids either in 1:1 (for 1a, 1e, 1f) or
2:1 (for 1b-1d) for 30 minutes, 30Hertz in the presence of the 30L of the methanol, as demonstrated
by comparison of PXRD plots of phase pure materials (1a-1f) with the simulated patterns of their
respective crystal structures.
Electronic Supplementary Material (ESI) for CrystEngCommThis journal is © The Royal Society of Chemistry 2013
Comparison of the PXRD pattern of (a) simulated crystal structure of 1a with the (b)
cocrystal 1a synthesized by liquid-assisted-grinding.
Comparison of the PXRD pattern of (a) simulated crystal structure of 1b with the (b)
cocrystal 1b synthesized by liquid-assisted-grinding.
Comparison of the PXRD pattern of (a) simulated crystal structure of 1c with the (b)
cocrystal 1c synthesized by liquid-assisted-grinding.
Electronic Supplementary Material (ESI) for CrystEngCommThis journal is © The Royal Society of Chemistry 2013
Comparison of the PXRD pattern of (a) simulated crystal structure of 1d with the (b)
cocrystal 1d synthesized by liquid-assisted-grinding.
Comparison of the PXRD pattern of (a) simulated crystal structure of 1e with the (b) salt
1e synthesized by liquid-assisted-grinding.
Comparison of the PXRD pattern of (a) simulated crystal structure of 1f with the (b)
cocrystal 1f synthesized by liquid-assisted-grinding.
Electronic Supplementary Material (ESI) for CrystEngCommThis journal is © The Royal Society of Chemistry 2013
SI-4: Crystallographic Table
Table 1: Crystallographic data for the adducts 1a-1f.
1a 1b 1c 1d 1e 1f
Formula 1(C9H9N5):
1(C7H6O2):
2(C9H9N5):
1(C8H6O4)
2(C9H9N5):
1(C10H10O4)
2(C9H9N5):
1(C10H10O4)
1(C9H10N5):
1(C8H5O4)
1(C9H9N5):
1(C8H6O4)
Formula Wt. 309.33 540.55 568.60 568.60 353.34 353.34
Crystal habit Blocks Rectangular
Blocks
Blocks Blocks Rod Shaped Blocks
Crystal color Colorless Colorless Colorless Colorless Colorless Colorless
Crystal
system
Monoclinic Monoclinic Orthorhombic Orthorhombic Triclinic Triclinic
Space group Pc C 2/c Pbca Pbcn Pī Pī
a (Å) 9.821(3) 29.943(1) 12.405(4) 31.500(7) 7.162(2) 8.504(6)
b (Å) 7.135(2) 7.007(2) 6.948(2) 12.412(3) 10.042(2) 10.199(7)
c (Å) 12.126(2) 12.152(4) 31.402(1) 7.016(2) 12.835(3) 10.258(7)
(deg) 90.00 90.00 90.00 90.00 68.27(1) 108.53(1)
(deg) 116.60(2) 107.78(1) 90.00 90.00 85.45(1) 91.79(1)
(deg) 90.00 90.00 90.00 90.00 71.46(1) 92.96(1)
V (Å3) 759.8(3) 2427.8(1) 2706.5(15) 2743.1(1) 812.2(3) 841.4(1)
Z 2 4 4 4 2 2
Dcalc (g cm-3
) 1.352 1.479 1.395 1.377 1.445 1.395
T (K) 298(2) 100(2) 298(2) 298(2) 273(2) 273(2)
(Mo-K) 0.71073 0.71073 0.71073 0.71073 0.71073 0.71073
(mm-1
) 0.094 0.105 0.098 0.097 0.107 0.103
2 range
(deg)
50.58 50.54 50.58 50.46 50.48 50.50
Limiting
indices -11 h 11
-8 k 8
-14 h 14
-35 h 35
-8 k 8
-14 h 14
-14 h 14
-8 k 8
-37 h 37
-37 h 37
-14 k 14
-8 h 8
-8 h 8
-12 k 12
-8 h 15
-9 h 10
-7 k 12
-12 h 12
F(000) 324 1128 1192 1192 368 368
No. of
Reflns.
Measured
7108 7497 18044 18397 4143 4255
No. Unique
Reflns.
2748 2210 2459 2487 2883 2967
No. of
Reflns.
Used
2498 1750 2152 2109 1607 1693
No. of
Parameters
210 206 234 225 265 259
GOF on F2 1.576 2.037 1.292 1.106 1.012 0.973
R1 [I2(I)] 0.0869 0.0871 0.0685 0.0642 0.0639 0.0594
wR2 0.2169 0.2998 0.1856 0.1617 0.1624 0.1387
Final diff.
Fourier map
(e-.Å
-3) max,
min
0.483, -
0.330
0.554, -
0.361
0.264, -0.389 0.420, -0.266 0.265, -0.304 0.254, -0.258
Electronic Supplementary Material (ESI) for CrystEngCommThis journal is © The Royal Society of Chemistry 2013
SI-5: Hydrogen bond table
Table 2: Bond length and angles of the hydrogen bonds observed in the adducts 1a-1f.
Hydrogen
Bond, D-H...
A
1a
1b 1c 1d
N–H...
N 2.14 2.99 170 2.08 2.97 166 2.12 2.99 168 2.11 2.98 170
2.31 3.16 172 2.32 3.18 174 2.16 3.04 172 2.21 3.06 169
N–H...
O
2.03 2.88 167 2.05 2.90 168 2.10 2.98 175 2.25 3.08 162
2.44 2.98 121 2.56 3.27 139 2.54 3.26 138
2.59 3.25 134
N–H...
O-
N+–H
...O
-
O–H...
N 1.79 2.61 173 1.78 2.59 170 1.73 2.63 172 1.85 2.65 166
O–H...
O
C–H...
O
C–H...
O-
SI-5: Hydrogen bond table
Table 2: continued..
Table 2: Bond length and angles of the hydrogen bonds observed
in the adducts 1a-1f.
Hydrogen
Bond, D-H...
A 1e
1f
N–H...
N 2.15 2.97 160 2.20 3.05 174
N–H...
O
2.09 2.77 136 2.01 2.86 173
2.28 3.10 159 2.10 2.93 162
2.59 3.24 133
N–H...
O- 1.99 2.84 154
N+–H
...O
- 1.87 2.78 173
O–H...
N 1.87 2.69 171
1.93 2.74 167
O–H...
O 1.59 2.40 167
C–H...
O 2.55 3.37 147
C–H...
O- 2.34 3.19 151
Electronic Supplementary Material (ESI) for CrystEngCommThis journal is © The Royal Society of Chemistry 2013
SI-6: DSC of various adducts (1a-1f)
1a melting at 216.70°C
1b melting at 312.70°C. The peak near 65 may be due to solvent adsorbed to the surface of sample.
Electronic Supplementary Material (ESI) for CrystEngCommThis journal is © The Royal Society of Chemistry 2013
1c melting at 229.15°C
1d melting at 205.04°C
Electronic Supplementary Material (ESI) for CrystEngCommThis journal is © The Royal Society of Chemistry 2013
1e melting at 194.17°C
1f melting at 247.28°C
Electronic Supplementary Material (ESI) for CrystEngCommThis journal is © The Royal Society of Chemistry 2013
SI-7: TGA of various adducts (1a-1f)
Electronic Supplementary Material (ESI) for CrystEngCommThis journal is © The Royal Society of Chemistry 2013
Electronic Supplementary Material (ESI) for CrystEngCommThis journal is © The Royal Society of Chemistry 2013
Electronic Supplementary Material (ESI) for CrystEngCommThis journal is © The Royal Society of Chemistry 2013
SI-8: Reference code of structures found in CSD containing Synthons 1, 2 and 3
Reference code of 2190
structures out of 5035
(frequency 43.5%)
containing Synthon 1
Reference code of 170
structures out of 289
(frequency 58.8%)
containing Synthon 2
Reference code of 772
structures out of 952
(frequency 81%) containing
Synthon 3
ELENUF01 ELEPOB01
FAZDAN
FAZDER FAZDIV
HOWRIV01
LEFRUL LEGDUY
LEGLIU
LEGZEE NAXSIQ
NAXWIU
NEBBED NEBVOH
NEBWEY NEBWIC
NEBWOI
NEBWUO NEBXAV
NEBXEZ
NEBXUP NEBYEA
SAXHIK
SAXHOQ SAXHUW
SAXJAE
VAXHIN VEBKIY
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XEGGUN XEGHAU
XEGHEY
XEGHOI XEGHUO
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ABEGAQ
ABEMIE ABEROP
ABIGIB
ABOCUR ABOMEJ
ABONEK
ABUHAZ ACAPID
ACEMEB
ACIKUS ACIVUE
ACIWAL
ACMCPY ACPYRI01
ACUHUB
ADBPPD ADELAX
ADHGND10
ADETOT BASYOL
BASYUR
BASZAY CAQLIQ
CIDCUO
CONYAF10 COQNAX
COVVIS
COWHOM COWHUS
COWJAA
COWJOO DAYWAC
DAYWAC01 DETJAO
DUCXOP
DUSKUY DUXSAR
DUXSEV
EPIVUV EPIWAC
EPIWEG
EPIWIK ETAZEF
EXEYIQ
EXEYOW EXEYUC
EXEZAJ
EXEZEN EXEZIR
EXEZOX
EXEZUD EXIBAP
EXIBET
EXIBIX EXIBOD
EXIBUJ
EXICAQ EXICEU
EXICIY
FAJMAE FOVWIX
FUHGUL
GIMPAU GODQIZ
GUZDEL
HOVLIN HOWQUG
IFACUO
JIQCAN JIQCER
JIWQIQ
KAHMOV KEKGAJ
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ABECEQ ABECOA
ABEDAN
ABEDOB ABELUP
ABUNUH
ACUHIP ADAVIK
ADIHOL
ADIJUT ADMINA
AFESOU
AJECEX AJECIB
AJICIG AJOFUA
AJOFUA01
AKOFUB ALUPAZ
ANENOX
ANENUD ANENUD01
ANEPAL
ARGIND11 ARUDAS
AWIJUM
AWUMAH AXASUO
AYUQAN
AYUXUO AZOQAI
BAGSAD
BANCID BECZUF
BEDBAO
BETNOD BEWNAT
BEWNAT01
BEWNEX BEXPUQ
BGCUCB
BGUDCB10 BICHAW
BIPQIA
BIZJEA BOBQEO
BOBQIS
BOJFEM BOPTEG
BOQBAK
BORYUD BOTSEJ
BOVTEM
BUYBIH CABNIE
CACBOY
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ADIHUQ
ADMEHH
ADMEHI ADPRTR
ADPRTY
ADUYUU ADUZEF
AFABUF
AFMIMZ AFOWAT
AFOWEX
AFOWEX01 AFOWEX02
AFUYAB
AFUYIJ AFUYUV
AFZPYM
AGIGIH AGIGUT
AHEGEZ
AHEGEZ01 AHEGID
AHEGOJ
AHEGUP AHEHAW
AHEKUT
AHIPEM AHMXTZ10
AHUMAR
AHUMIZ AHUMOF
AHUMUL
AHUNAS AIMZCX10
AJAKOL
AJAPIL AJAPIL01
AJAPIL02
AJAPIL03 AJAPIL04
AJAPOR AJAPOR01
AJAQOS
AJIPOZ AKAYOB
AKEDUQ
AKEWUI ALESEQ
AMADCS
AMADCU AMAZBR
AMBZPY
AMCLPY AMCLPY11
AMCLPY12
AMCPYZ AMCQUN
AMEPYD
AMEROZ AMMEPY
AMMTAZ01
AMNTPY AMNTPY01
AMNTPY02
AMPIBR AMPTRA10
AMPTRB10
AMPYRD
AMPYRM01
AMPYRM10
AMPYRZ AMQUIN
AMSCNI11
AMSMPI AMTHTZ
AMTZLA
AMXBPM10 AMXBPM11
AMXPYZ
AMXZPY10
KIXVES
KURGOU
KURGOU01 KUZZUB
LADDAX
LADDEB LEWPUY
LEWRAG
LEWREK LEWRIO
LEZHAA
LEZHEE LOMTAI
LOMTEM
MAQBEM MIRQEJ
MODPAX
MOXTUP MUBRAD
NEXXIX
NIFCAH NIQNIL
NIQNIL01
NUHMEI NUHMIM
NUKWEW
NUKWEW01 NUKWOG
NUSHIT
OFUHUS PEQPAD
PEQPEH
PEQPIL PEQPOR
PEQPUX
PEQQAE PEQQEI
PEQQIM
PEQQOS PUJBOM
PUJNIS PUKDIJ
QAKRIF
QAMNID QAWTUE
RADFEI
RADGAF ROGPIN
ROGQUA
SERMOR SERMOR10
SIYCEJ
SIYCIN SOVNIA
SUVJEY
TALDAN TALDIV
TAWSOB
TAZWOH TAZWOH01
TETXUL
TIPFII ULECEU
UXOBEP
UXOBIT UXOBOZ
UYAZEA
VAPFEX
VOCZET
VOCZET01
VOCZET02 WINMIQ
XOJMOZ
XOJMUF XOJNAM
XOJNEQ
XOJNIU XOJNOA
XOJNUG
XOJPAO
CAFKID
CAGCUJ
CASCIJ CAXNUK
CEBZUE10
CEKVAP CELHOR
CELHUX
CESRUN CEWBOW
CICZUK
CIDCIC CIDCOI
CIDCUO
CIKRIY CINXED
CINXIH
CIQBIO CIRVUV
CIRWAC
COFBOO10 COSFUM
COWJEE
COWJII COWJUU
CREATH01
CREATH03 CREATH04
CREATH05
CREATH06 CREATH07
CTSGLM
CUCSEY10 CUDREY
CUGNEX
CUNVUD CUNVUD01
CUWROB
CUWWOG CUWWUM
CUWXEX CUWXIB
CYTBGL01
CYTFGL DADBEQ
DAMQEP
DAMQUD DEBMOM
DEBMOM01
DEHSAK10 DENWUP
DENWUP01
DENXAW DEWYOU
DEXNIE
DEYBUF DIYZIU
DOCMAK
DONMAU DOTGID
DOTWOZ
DUCSOK DUFDIR10
DUFDOX10
DUJKID DUJKOJ
DUMJEA10
DUMPUW
DUNCOF
DUPFUQ
DUPJEE DUSJIL
DUSKIM
DUSKOS DUSLUY
DUSMOU
DUSMUA DUSPUD
DUSQAK
DUSYIA
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ANOYEI
ANUXAJ
APIQOG APIVUR
AQILOC
ARUDAS ARUQOT
ARUTIQ
ASENES ASICAH
ASINUL
ASOVUZ ATDZDX
ATDZPY
ATURUC ATZCXA
ATZQZN
AWEROK AWERUQ
AWOJUS
AYAKER AYOKUV
AYOLOP
AYOVAM AZADMS10
AZIGUL
AZOQAI AZUYUQ
BABRUR
BABTAB BADXOT01
BADXUZ01
BAFREF BAJYIV
BAKBIZ
BAKCOF BALZAR
BAMBEY
BAMLOR BAMMUY
BAQNUC BAQSUH
BAWKEP10
BAYXUU BAYXUU01
BAYXUU10
BEBZIR BEDLUR
BEDPUW
BEGBAQ BEGZUI
BEHPUZ
BEKJEG BEQWAW
BERFUZ
BESSUO BEWHAM
BGUCRM
BGUHCL BGUSUL10
BIFWES10
BIFYOE BIGUAN
BIGUAN01
BIKFAC10 BILROD
BILVIC
BIMSAR
BIPRAT01
BIQQOH
BIRMEU03 BISMAR
BISQAV
BIVVIL BIYQOQ
BIZCAP
BNZSCU01 BNZSCU02
BOFVIC
BOFXAW
XUVQEL
XUVSAJ
YIRLOB ZAJHOH
ZAJJAV
ZAJJEZ ZAPGII
ZERNAL
ZUKXAE ZUKXEI
ZUKXUY
KEBQIT NAXSOW
NEBVOH
NEBWIC NEBWOI
NEBWUO
NEBXAV NEBXEZ
NEBXID
NEBXOJ NEBXUP
VAXHEJ
VAXHIN ACERIL
CEGGUS
EFAPUY PECWEB
WEDKUN
WEDLAU WEDLEY
WEDLOI
WEDLUO WEDMEZ
DUTNUC
DUTZOI
DUVCIH DUZNIW
DUZPUK
DUZQAR EBAWAH
EBAZOY
EBAZOY01 EBOKIP
EDATOS
EFAZOA EFUNOJ
EHACIA
EJAFAW EJATOY
EJATUE
EMIHAJ EPIVIJ
EPIVOP
EROHOJ ETAYUU
ETAZAB
ETAZIJ ETAZOP
ETAZUV
ETIGUJ ETIGUJ01
ETIZOW
EVASAW EWINAZ
EWOTUG
FAFNOR FAKWEV
FAYFAN
FECZES FEDPUA
FEQLES
FETTOO FETTOO01
FIWJIF FIXTAI
FOLROO
FONMEB FOVBUO
FOVMEI
FOWMUA FOXLUA
FOXMAH
FOXMEL FOYMAH
FUGXIO
FUHKEZ FUHNIG
FUHPOO
FUHVOU FUWVAU
GADMUT
GALQAM GAPJEO
GAQJEP
GATMIZ GAVLEV
GAWBUC
GEKYOK GELHEK01
GIGZIG
GIHCIK
GIHGEK
GINMOG
GINNIB GIPHES
GIPHIW
GIVBUJ GODMUI
GOLFOC
GOLXUB GUACET
GUACET01
GUACOT
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BOFZAY
BOJGEN
BOMTAY BOMTUS10
BONQAW
BOPTEG BOQRAB
BOQREF
BOQRIJ BOQROO
BOTQAD
BOTVIQ BOTZOA
BOWZAP
BOYGAY BUCYAA
BUDDUA
BUDWAY10 BUFPEX
BULYOX
BULYUD BULZEO
BULZOY
BUMWEL10 BUMWIP10
BUPMAA
BUPMAA01 BURQUB
BURXIW
BUYGEI BZAPCX10
BZAPUC20
CAADNS10 CABYIO
CAFQUW
CAGBES CAGBES01
CAGCET
CAJWUG CAJWUG01
CAJXAN CALFAY
CALFEC
CALVES CAQLEM
CATFIO
CATKUF CATNES
CATNIW
CBHTAZ10 CEDDAR
CEDDEV
CEFTUC CEFVAK
CEJHAA
CEJSOZ CEKFON
CEKGUV
CEKJOR CEQZAA
CEQZOO
CERKUG CETZEH
CEXLEX
CFTXIM CICZUK
CIDCIC
CIDWOB
CIDWUH
CIHKOT
CIHSIW CIHSOC
CIKCEF
CIMJEN CIQLET
CISHUI
CIVDEQ01 CIWWAG
CIXTOS
COBLEL
GUANCB
GUHFOE
GUHOXM GUHOXM01
GUHOXM02
GUPICL10 GUPRAC
GUTSET
GUVFOS HAMYIE
HATTIG
HEGHOR HEJPOB
HEJPUH
HEKSAR HEVSAC
HEYJAX
HEYJIF HIBPOX
HIGFUZ
HILPOI HIQKUN
HIVYOB
HOCGEL HOCGIP
HOCGOV
HOFDEL HOLPON
HORGUQ
HOWQUG HOWRIV
HURMOW
HURMUC HUTNAL
HUTNEP
HUYLES HUYTEB
HUYYAB
HUYYAB01 HUYYAB02
IBOKEP IFIDAD
IFIDUW
IFUPUV IGAMUZ
IHAQOX
IHESOD IJONOL
INEFIQ
INEFIQ01 IPODOH
ISIBUI
ISICIX ISUTUL
IVEZEP
IWIRAH IWIZAQ
IYAWUB
IYAXAI IZEDAS
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JASHOB JAXFOE
JAXGAR
JEBGON JECYUL
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JEFLIQ
JEJMUH
JEKKIU
JEWCUK JIQCOB
JIWQIQ
JOGTEF JOGTIJ
JOGTUV
JOGVAD JOTLIN
KABHIE
KABKEF
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COCVEV
CODLEN
CODYUP10 COJMUJ
COJTAW
COLWOP CONRED
CONZUB
COPBAL COQZIS
COTGEY
COWHAY COWJAA
COWJOO
COWJUU COWLAC
COXJUV
COYVER COYVIV
CREATI02
CUCQEW CUCSEY01
CUCSEY10
CUGCEM CUGGUH
CUHGAO
CUJSAB CUJSEF
CUKCER
CUPMAB CYAMPD01
CYAMPD03
CYGUAN01 DACSUX
DAFPUV
DAFRAD DAFTOT
DAHNEG
DALWES DAMTRZ11
DAMTRZ20 DAMVAP
DANQOY
DAQHEJ DAQHOS
DARGAE
DATZUV DECYUF
DEFXUH
DEGBUN DEMHAF
DEPBEG
DEPRIZ DEQTUO
DESLOD
DETJAO DETKAP
DEWRAY
DEWYOU DEYVOT
DEYVUZ
DEYVUZ01 DEZXIQ
DIAVER
DIBMEG DICYUK
DIGTIX
DIHSUI01
DIQLEU
DISGES
DIVWAG DIWBIV
DIWCOB
DIWLAX DIWMEC
DIWWUC
DIYXIT DOJJOC
DOKWUW
DOLBUC
KADFUR
KADGAY
KAJTAS KAYXUD
KEFZAX
KEKGEN KEMBEK
KERFUJ
KIBKEL KIWLEI
KUFBUI
KUFCAP KUFCIX
KUQQUJ
KUQRAQ KUQREU
KUSTEY
KUSVAW KUSVAW01
KUSVEA
KUTXUT KUYNAU
KUYZUA
KUZJIZ LADBEZ
LADBID
LADBOJ LADBUP
LALCOQ
LAPFAL LAPMUL
LAPMUL01
LAPNAS LAPNEW
LAPNIA
LAPNOG LAPNUM
LAPPEY
LAPPIC LAQGOA
LARGIN02 LARRIG
LARROM
LAVYUD LAVZAK
LENKEV
LEPVIM LEWPOS
LEWROU
LEWRUA LICGIO
LILHIX
LISZES LOLDAS
LOLDEW
LOLDIA LOLDOG
LOMTIQ
LORRIT LORWEV
LUDKAW
LUPZOL LUPZOL01
MAMLAO
MAQBAI MAQBEM
MAQBIQ
MARTEE
MAWGUM
MENBIR
MIFQOH MIFWUT
MISMAC
MOPPEM MOSMIR
MOXTAV
MOZNAR MOZPUN
MOZXOP
MUPNUG
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DOLCAJ
DOVCAT
DTBIPT DTHBPD10
DUBKER
DUCSOK DUKGAS
DUKGEW
DUKHOH DUKHUN
DUKKOJ
DUKPIJ DUKPOP
DUKVAG
DUPYIW DUTSAM10
DUTSEQ10
DUTTOC DUXDIJ
DUXDOP
DUXWAU DUXWIC
DUYLEP
DUZHAH DUZHEL
DUZROG
DXCYTD EADPBA
EATZAC
EBILEI EBONAM
EBONEQ
EBONIU EBONOA
ECAFEU
EDUMOG EFAWAJ
EFAZOA
EFEMUX01 EFOMUI
EFONUJ EFOTUP
EFOVAX
EFOVEB EFOVIF
EFOVOL
EFOVUR EFOWAY
EFOWEC
EFOWIG EFOWOM
EFOWUS
EFOXUT EFOYEE
EFOYII
EFOYUU EGMCYT10
EGMFCY10
EGUANC EGUTCP
EHACOG
EHEVUI EHEWAP
EHINAK
EHINEO EHUYIQ
EHUYOW
EJADUO
EJESUH
EJIZOM
EKEGUX EKEHEI
EKELEL
EKELIP ELENUF
ELEPOB
ELEYID ELEYID01
ELOVOR
EMAVAQ
MUPPAO
MUTBAF
MUTLUJ NAGLYB10
NAPSEE
NATHEW NEGQIA
NEGQOG
NEGRAT NEGREX
NIQCOG
NOFYEM NOQHEG
NOQHIK
NOQHOQ NORGEH
NOSXAU
NOSXEY NOTBAZ
NOTPAN
NUMVIA NUQVEB
NUTVUT
NUWNAU OBECIJ
OBUPOS
OCAGAC OCEMUG
ODAZID
ODAZID01 ODAZID02
OJOSUC
OJOVEO OJUJOS
OJUVEU
OMIJEZ OQUMOD
OQUMUJ
OSISAL OVUMEY
OVUMIC PABQEO
PACDEC
PACDIG PAHLAN
PAJBUY
PAKNOG PANSAA
PAQRIK
PAQROQ PARWOV
PARWUB
PARXEM PARXIQ
PAVXIV
PAXHAZ PAXQOV
PIGQUS
POXSOL POYLIY
POYMAR
PUGRUF PUJDAA
PUJJOU
PUJKOV PUJWEX
PUJWIB
PUKDEF
PUKDOP
PUKJIP
PUKJOV PUKZUR
PUNPIY
PUNPOE PUNPUK
PUNQAR
PUWTOQ QADHAE
QAGJAJ
QAGJEN
Electronic Supplementary Material (ESI) for CrystEngCommThis journal is © The Royal Society of Chemistry 2013
EMIKAM
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EMIKOA EMIKUG
EMISEY
EMISUO EMITEZ
ENAGUW
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EPICEM
EQACAB EQACEF
EQACOP
EQILOG EQIYAE
EQUBEX
EROZUH ESAQEU
ESESEA
ESEXAB ETASIB
ETAYUU
ETAZAB ETAZEF
ETAZIJ
ETAZOP ETAZUV
ETETIG
ETIGUJ ETIGUJ01
ETIQON
EVAQUO EVENAU
EVENEY
EVIGAR EVIKAV
EVITEI
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EWANIA EWANOG
EWEKAS
EWOCUP EWUYOL
EWUYUR
EXAXAD EXAXEH
EXEKEY
EXEKIC EXEKOI
EXELID
EXELOJ EXEMUQ
EXEYIQ
EXEYOW EXEYUC
EXEZEN
EXEZIR EXEZOX
EXEZUD
EXIBAP EXIBET
EXIBIX
EXIBOD EXIBUJ
EXICAQ
EXICEU
EXICIY
EXIHAV
EXOSAM EXUGEJ
EXUQAP
EXUQET EYECOB
EYIXOZ
EYIXUF EYUKEP
EYUKEP01
EZOTOD
QAGJIR
QAGJOX
QAGJUD QAJKET
QAKCUC
QALDOY QAMNEZ
QAMNID
QAMXEI QAMXIM
QANPEB
QEQTUB QEQVIS
QIFFIU
QIFFOA QOVROJ
QQQFGS10
QUBRAH QUFDAX
QUFDEB
QUFDIF QUFDOL
QUFDUR
QUPSIE QUPTAX
QUPTOL
QUWXAI QUWXEM
QUWXIQ
QUYCAP QUYFEW
RADDUW
RADFAE RADFIM
RADFUY
RADGEJ RATJEC
RAVGIF
RAZWUL RAZXAS
REGKUK RIFXEK
RIGBEO
RIGMEA RIGMIE
RIZBUY
ROFLAZ ROFVEO
ROGPOT
ROGPUZ ROGQAG
ROGQEK
ROGQIO ROGQOU
ROGXIU
ROGXIU01 ROJFAX
ROJGON
ROMZOJ RONBUS
RONBUS01
RUVPEE RUZPIL
RUZPOR
RUZQOS SABFEI
SABKEN
SAGGUE
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SEFXIL
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FACKIE FADHUO
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FAGSUB02 FAKTUI
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FATHEN
FAXKIZ FAXSUT
FAYJIZ
FAZFES FAZFUI
FAZXIO
FEBDIA FECSIQ
FEDTAK
FELRUJ FENMEQ
FENMEQ01
FERDOW FESCIQ
FETSEC
FETTOO FETTOO01
FEYGOG
FEYGUM FEZBIW
FEZJIE
FIBGEC FIBWIX
FIFJUZ
FIFRER FIHKEM
FIJKEP
FILSAV FILSAV01
FIPREB FIRNID
FITXIP
FITZAJ FITZAJ01
FIWRAE
FLYITU FMPTER
FOGVIG01
FOGVIG04 FOGVIG07
FONMEB
FORJUR FOSGIE
FOSVEP
FOTXES FOVFIG
FOVHUT
FOVQOW FOWQOY
FOXBEA
FOXROA FPYSNI
FUBLAQ
FUFQUS FUHKEZ
FUPKOQ
FUREAP
FURGAA01
FURGAA02
FURPAJ FUWVAU
FUXKAL
GABTEK GACNUU
GACNUV
GACPAC GADCIX
GADPUX
GAFTIQ
SOFXOA
SUYNUW
SUYQAF SUYXIU
SUYYAN
SUYYIV SUZBEV
SUZNEH
SUZSOW SUZXUH
TADRUM
TAKZUC TALDAN
TALDER
TAMSAC TAQBIY
TARXAL
TATWUI TAVFOM
TAVFUS
TEFLUL TESVIX
TETXIZ
TETXOF TEVRAO
TIDCAK
TIHGUN TILSUD
TMPFOR01
TORQIA TORQOG
TOYLOI
TOYTEG TOYTIK
TOYTOQ
TUDLOT TUPTUU
TUPVAC
TUQGUI TUQKEW
TUTFIY TUTFOE
TUTGAR
TUTGEV TUTGIZ
TUWCOE
UGUKEM UHAYEH
UHAYIL
UHUCUV UJOCOM
ULAXIO
ULAXOU ULAXUA
ULAYAH
ULEHID ULEKUS
ULINOS
ULINOS01 UNOFAF
UNOGUA
UPOBIL UVOKEW
UVOKIA
UYEYIH UYODES
UYOREG
UYOROQ
VABLOZ
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VAPLIH
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GAPPIY GAQFEL
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GATDUC GATJOC
GATJUI
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GEGZIB
GEKTIA GEKTOG
GELGEK
GELGIO GENKOA
GERBOU
GERBUA GESCIQ
GETVOR
GEVKUO GEYXOX
GIBHUU
GICWAR GICWEV
GICWIZ
GICWOF GICWUL
GICXAS
GICXEW GICXIA
GICXOG
GIDMEL GIFZAW01
GIGQOD
GIHFAF GIHHEK
GIJMER
GIJTID GIJTID01
GIJTOJ GIJTOJ01
GIKMUI
GILGOY GIMPAU
GIMRIE
GIMZUY GINMOG
GIRKOI
GIRNIF GIRNOL
GIRNOL01
GIRNUR GIRPAZ
GIRPED
GISDES GISDES01
GISVAG
GITKUQ GITPAB
GIVYAL
GOCHIQ GOCHUC
GOCJAK
GOCJEO GOCJIS
GODDUY
GODFAG
GOLMEZ
GOMKEY
GOMKIC GOMKOI
GOTMEH
GOTMIL GOTMOR
GOTMOR01
GOTMUX GOVKEH
GOVKIL
GOXCIF
VAQSOW
VAQSUC
VAQTAJ VAQTEN
VAQTOX
VAQTUD VAQVAL
VASFUS
VATVET VATVET01
VAYYIE
VOCZAP VULTOM
VUZBAT
WABHOX WADKOD
WADTEC
WAFKEV WEPTIV
WEPTIV01
WETGAE WIJNEI
WIJNIM
WIJNOS WIJNOS01
WINJUZ
WIPZAW WIPZAW01
WIPZEA
WIPZEA01 WIPZIE
WIPZIE01
WODGIG WOHDIG
WOQWII
WOQWOO WOSBEL
WOYPIJ
WUKZEH01 WUVKUU
WUVLAB WUVLEF
WUVLEF01
WUWDEY WUWDIC
WUXDEY
WUZRUF XAGFAM
XANDAR
XAPXAN XAPXER
XAPXIV
XARVOB XAVKOV
XAVTIZ
XAZRIA XEBPAV
XEBPID
XEGLAW XINRUH
XINRUH01
XINSES XIQCEF
XISTID
XIXTUU XOKSAR
XUVPOU
XUVQEL
XUVRIP
XUVROV
XUVRUB YAGKEY
YAHQOO
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YAJHUO
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YEJZAO
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GUANCD GUANCD01
GUANCD02
GUANCH01 GUDYUA
GUFDOB
GUGNAX GUGNIF
GUGNUR
GUKROT GULHAW
GULHEA
GUNPIC10 GUSZUQ
GUTSET
GUXKUG GUYTOK
HACNUV
HAGRUD HAKJIM
HALHOT
HALXOJ HALXUP
HANPUH
HANRAP HAQBIM
HAQVIG
HAXRAB HAXWIO
HAYMUR
HAZGIY HEGFUV
HEGHIL
HEKNIU HEKXAW
HETZAI
HEVQAB HEYHUP
HICDIG HICVEU
HIDXOI
HIFNIT HIFNOZ
HIFVEX
HIJCUY HIJFIP
HIJFIP01
HIKSEZ HILFIS
HIMMEW
HIMMIA HISCIW
HISFUL
HIVSUB HIZHII
HOBVEA
HOBVIE HODSIC
HOFCEL
HOFFUD HOFHUG
HOLFAP
HOLFAP01 HOLKUP
HOMLIF
HOPBOD
HOPBUJ
HORTUE
HORTUE01 HORVAM
HORVEQ
HORVIU HORVOA
HORVUG
HORWAN HORWER
HORWIV
HOSQUB
YEMJAB
YEXFUD
YEYMEV YEYWUV01
YICCIX
YIZCIU YOVQUW
YOVQUW01
YOWDET YOWDIX
YUHVUS
YUQKOL YUQKUR
ZAJHUN
ZANYOE ZARHOR
ZASYUP
ZAYHEO ZERMEO
ZERPUH
ZERQES ZIVROL
ZOJXIF
ZOJXOL GAXFOC
GAXFUI
HOWRIV01 KEBJOS
KEBJUY
LEGZEE NAXSIQ
NAXWOA
NEBVUN NEBWAU
NEBWEY
NEBYAW NEBYEA
QEDHIS
SAXQIT VAXRIX
XEGGUN XEGHAU
XEGHEY
XEGHIC XEGHOI
XEGHUO
XEGJAW CEFTEO
EDUXEI
EDUYUZ EFAFIC
EFALII
EFALOO FEFKIM
FEFKIM01
KELVOO KELVUU
PAZFON
SECKUI SECPUN
SECWEE
SECXIJ SECXOP
VEQKIN
WECXAF WECXEJ
WEDKEX
XEMPEM
XEMPEM01
YEHWIT
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HOVLIN HOWRIU
HOWRIV
HOXZID HOXZOJ
HOXZUP
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HOYPIV
HOYYUQ HUBPAV
HUCBIR
HUGQAC HUHJEA
HUHWEM
HUMYOE HURMUC
HUTVAU
HUTVIC HUVGUB
HUXLOC
HUXLUI HUYBUY
HUZLUJ
HUZSEA IBAKUT
IBALAA
IBALEE IBALII
IBALUU
IBAMAB IBAMEF
IBIDIG
IBIDOM IBIJAF
IBIJEJ
IBIJIN ICACUL
ICECIC ICYTIN
ICYTIN01
IDAMEG IDAMIK
IDAMIK01
IDAMOQ IDAXAN
IDILUC
IDUVUZ IFELAH
IFIDUW
IFOYIM IGINUI
IHEKIQ
IHELAJ IHELEN
IHOZEK
IHUFAS IJAHOR
IJELEP
IJUKED IKALUC
IKEDAE
IKOJIB IKOJOH
ILAFOR
ILAYIE
ILONOM
IMIVOP
IMPTHA12 IMTAZO01
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IRORIQ IRUFAD
IRUGAE
ISIPUV ISUNAL
ISUNAL01
ISUTUL IVAYOT
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IWIZAQ IWOCUS
IWOKEL
IXAMAV IXATEG
IYIFEC
IZECAS IZECUL
JABCUL
JABDAS JAGWIY
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JAJPOA JAJPUG
JAKJUA
JAKKAH JAMRIY02
JAQKUI
JASTIH JATCOW
JAVJIA
JAWPIH JEBPOW
JECMIN
JEDMUA JEHCUU01
JEJDOS
JEJDUY JEKGEL
JEKGIP JEPJUK
JICLAI
JIKHOA JIMKOF
JIMMUO
JIQCAN JIQCER
JIQCIV
JITYOB JITYUH
JIWQIQ
JIXGUS JODHOA
JOLJID
JOWWIB JOWWOH
JOXTIZ
JOXTUL JOZYUS
JOZYUS01
JUFKEA JUFZIT
JUJFID
JUKVOA JUPPAL
JUZCAI
KABDEY
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KAHZOK KAHZUQ
KAJFIK
KAJFIK10 KAJGEH
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KANSUP KAPBIM
KAPHIU
KARYEI KEKGUD
KEPQAY
KEQLEY KEQPOL
KEQWIM
KERDIU KERVIN
KESXEM
KESZAJ KEWGEZ
KEWJIF
KEWXAM KEWXEQ
KEXLAB
KEZDUP KIFQAS
KIGQIA
KIHSEA KIJZAF
KIWLEI
KIWNEK KIWVIW
KIWVIW01
KIWVIW02 KIWYAR
KIWYEV
KIWYEV01 KIWZIA
KIXLIN KODFEO
KOGXIO
KOKPOP KOWTAR
KOWTEV
KOXBOO KUCKOI
KUCNAY
KUFBUI KUJFOL
KUKGUS
KUPVUM KUQQOD
KUQQUJ
KUQYUR KUSQEV
KUTLAM01
KUTTAV KUZMUO
LACBEW
LACXEU LAFNIQ
LAGCUS
LAGMEM LAHJUZ
LAHTUL
LALKOZ
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LAMLUG LAMLUG01
LANBOT
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LEFMUF LEFYOL
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LEFZAY LEFZEC
LEFZIG
LEJLER LEJYAB
LEJYEF
LELNUM LELPOI
LENKEV
LESLIF LEWBAR
LEWBEV
LEWPUY LEWREK
LEYXUI
LEYYAP LEYYAP01
LEYZIZ
LICZOM LIHCOU
LIJJAP
LIJJAP01 LINFOD
LIPWEM
LIPWEM01 LIPWEM02
LIQPAD
LIQPEH LIQPIL
LITNEH
LITQOU LIVKAD
LIXNEM
LIYGIJ LOBFAK
LOBFAK01 LOBFEO
LOBPOI
LOHROQ LOKYAM
LOLCUL
LOLSOU LONXOC
LORRAL
LORXAS LOSYOH
LOTXUN
LOTYAU LUDXOX
LUDXUD
LUDYAK LUDYEO
LUFAEP10
LUHBAS LULVOE
LUPCGS
LUPVOH LUPVOH01
LUPVUN
LUPWAU LUPWOI
LUPWUO
LUPZUR
LUQBAA
LUQBEE
LURCUX LUVNAS
LUVPIB
LUWCOV LUWHAM
LUWHEQ
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MACQIS MAFXOH
MAHSEV
MAHYUP MALWIG
MAQBAI
MAQBEM MAVZAL
MAVZEP
MAWXOX MAWXUD
MAXYOZ
MAXYUF MAYGID
MAZADN
MAZZIX MEBHAD
MECYTS
MECYTS01 MEHZUU
MEKGOZ
MEKLUJ MEKLUJ01
MEKMAQ
MELAMI01 MELAMI02
MELAMI03
MELAMI04 MELAMI05
MELAMI06
MELAMI07 MELXIL
MELYOS
MEMKIY MEMKUK
MENRED
METCYT01 METSAG
MEVWEP MGUCUS
MHPTEC
MIDNUJ MIFROI
MIFSOJ
MIFWUT MIKTOQ
MIMSEG
MIMSOQ MIMSUW
MIWFOO
MIWFOO01 MIWFUU
MIXGEG
MOBYIL MODJUL
MOFDER
MOGLAV MOGQII
MOJDIZ
MOLFOJ MOLFUP
MOLVUE
MOLWAL MOPPUC
MOPPUC01
MORBGB
MOSPIU
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MOXSUO MOXTEZ
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MTYDAP MUBLEB
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MULYOI MUQVIE
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MURKIU MUTJER
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MZPYPM NADSEQ
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NAGLAJ NAGLEN
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NAMGCU
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NARBIS NARBOY
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NERJIE NERJOK
NERJUQ
NERKEB NERKIF
NEVNUY NEVXIV
NIBDIM
NIBDIM01 NICGAH
NICGEL
NIGNEX NIGNIB
NIGNOH
NIGQOK NIGSIF
NIJNOK
NIJWAF NIKSIK
NINCIX
NINCOD NIQNIL
NIQNIL01
NIXPEP NIYDOO01
NODDEQ
NOFBUF NOFZOX
NOJGID
NOJKED NOPDAY
NORDUU
NOTSAQ
NOTSAQ01
NOVCAC
NPHPYM10 NUDKON
NUDVEN
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OBETUM OBEZAY
OBEZIG
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OBUPOS
OCATOB OCATUH
OCESIA
OCINIY ODOTUX
OFEXAY01
OFEYAZ OFEYED
OFOXAJ
OFUHOM OGANIU
OHODIZ
OHOHUP OJOSUC
OKISAD
OLAREY OLOBAS
OLOWIV
OMIJEZ OMOKUW
ONATON
OPASEE OQIKEF
OQOTEU
OQUQEX OQUQIB
OQUQOH
OQUQUN OQURAU
OQUREY OSOGUZ
OSOHAG
OSOHEK OSOHIO
OVUGES
OVUGIW OVUGOC
OVUGUI
OVUHAP OVUHIX
OVUMEY
OVUMUO OVUNAV
OWOZEG
OWUWIN OXAYAO
OXOSOK
OXOTAX PABCEC
PABYEW
PACMOX PACXIA
PACZUO
PAHBUW PAHBUW01
PAHDOS
PAKRIE
PAMLIA
PAMLOG
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PANKOF PANSAA
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PAVVUE PAWHEB
PAWWOB
PAXQUA PEBGUC
PEBGUC01
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PEDKEP
PEHYEH PEKPEA
PEMQII
PEMXEL PEQPUX
PEQQEI
PEQQIM PESQOU
PEYFUV
PIDBUA PIGTAB
PIJDER
PIJDIV PIKSAE
PINDIZ01
PIVROB PIXKOX
PIZNAO
PIZNIW POCPIH
POCPON
PODLAV PODQOP
POFPEG
POGPUX POMRIT
POSHIO
POWBOT PRMESA10
PUBHOK PUBYER
PUFGAZ
PUGWEU PUJBOM
PUMHIP
PUNPUK PUNQAR
PUPBAD
PUPBAD01 PUPBAD02
PUQVIH
PUTTAZ PUTTAZ02
PUZKUQ
PUZVIQ QACFOP
QACPEP
QAFRAR QAGPOE
QAGPUK
QAGQAR QAJRUQ
QAJVUU
QAKCUC QAKSIF
QAMKEW
QAMNID
QAMPOJ
QANJUL
QARHUM QARJAU
QARJEA
QARJEY QASDOE
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QAZYAR
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QELPED
QELQAA QERNIL
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QEZNIT
QIGVOR QIKDIX
QITQEP
QIWXOK QIZHIQ
QIZHIQ01
QIZHOW QOKROY
QOKWET
QOMXIZ QOTQOG
QOVQAU
QOYFOZ QUDKUW
QUIASP10
QUKSUL QUSDUE
QUWXEM
QUWXIQ QUYFEW
QUYYUF
RABNUZ RACBIH
RAFQOG
RAFZII RAGPIZ
RAJBAH
RALDOX RALPUQ
RANPIG RANPOM
RANPUS
RAPQAB RARCIX
RARCOD
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RARDEU
RARQOR RARZAM
RASSUZ
RAVQIO RAWBAS
RAWBAS01
RAWBAS02 RAWBAS03
RAWBAS04
RAWBAS05 RAWBAS06
REFJOC
REFJUI REGKOD
REGKOD01
REGWOP REMMOM
REMTUY
RENMOM
RENNAA
RENNEE
RENTAF RENTOT
RETQIQ
REVTUI RHODHY
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RIJVOV
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RISPEP RISVAQ
RIWLOY
RIYHOW RIYMIW
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ROGCEW
ROGPIN ROGPOT
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ROGQIO
ROGQOU ROGQUA
ROJGIH
ROJGON ROKCOJ
ROKPEM
ROLSER ROMZOJ
RORJOX
RORNAN RORNER
RUBVEQ
RUFGEF RUFTUI
RUFYAT
RUGQAM RUJPOC
RUKBAB
RUKGUZ RULVUQ
RUPSAW
RUQWAC RUTLEX
RUYKEC RUZMII
SAGZEG
SAGZIK SAHGOZ
SAHKAP
SAJSAZ SALYEL
SANWUA
SAZGUW SECKEQ
SEFSOL
SEGRUR SEMNAA
SEQFIE
SEQJED SERRAJ
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SETHII SETLOS
SEWZOJ
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SEYDIJ03 SEZDOR
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