Supplementary Information (SI-1 to SI-8) SI-1: Preparation of … · 2013. 5. 14. · SI-1:...

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.


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.


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.


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



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-


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


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.


1c melting at 229.15°C

1d melting at 205.04°C


1e melting at 194.17°C

1f melting at 247.28°C


SI-7: TGA of various adducts (1a-1f)


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



(frequency 58.8%)

containing Synthon 2



(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

XAYVIE

XEGGUN XEGHAU

XEGHEY

XEGHOI XEGHUO

XEGJAW

XEGJEA AADMPY10

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

KEKGUD

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


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


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


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

IZIJEH

JASHOB JAXFOE

JAXGAR

JEBGON JECYUL

JEFLEM

JEFLIQ

JEJMUH

JEKKIU

JEWCUK JIQCOB

JIWQIQ

JOGTEF JOGTIJ

JOGTUV

JOGVAD JOTLIN

KABHIE

KABKEF


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


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

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1. a) Siemens, SMART System, Siemens Analytical X-ray Instruments Inc., Madison, WI (USA), 1995; b) G. M. Sheldrick, SADABS Siemens Area Detector Absorption Correction Program, University of Gottingen, Gottingen, Germany, 1994; c) G. M. Sheldrick, SHELXTL-PLUS program for crystal structure solution and refinement, University of Gottingen, Gottingen, Germany. 2. A. L. Spek, PLATON, molecular geometry program, University of Utrecht, The Netherlands, 1995. 3. Diamond—Crystal and Molecular Structure Visualization, Version 3.1f, Crystal Impact, Brandenburg & Putz, Bonn, 2008.


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