Synthesis and fluorine-mediated interactions in methanol-encapsulated solid state self-assembly of an isatin-thiazoline hybrid

Article abstract of DOI:10.1016/j.molstruc.2015.06.013

An exciting isatin-thiazoline hybrid molecule 2 having -CN-NC- linkage has been synthesized in 88% yield by the reaction of 5-fluoroisatin with N-(4-fluorophenyl)hydrazinecarbothioamide followed by condensation of the resultant isatin-thiosemicarbazone in

Full text of DOI:10.1016/j.molstruc.2015.06.013

Accepted Manuscript
Synthesis and fluorine-mediated interactions in methanol-encapsulated solid state
self-assembly of an isatin-thiazoline hybrid
Humayun Pervez, Maqbool Ahmad, Taibi B. Hadda, Loic Toupet, Muhammad
Moazzam Naseer
PII:
S0022-2860(15)30037-5
10.1016/j.molstruc.2015.06.013
MOLSTR 21564
DOI:
Reference:
To appear in: Journal of Molecular Structure
Received Date: 12 April 2015
Revised Date: 2 June 2015
Accepted Date: 2 June 2015
Please cite this article as: H. Pervez, M. Ahmad, T.B. Hadda, L. Toupet, M.M. Naseer, Synthesis and
fluorine-mediated interactions in methanol-encapsulated solid state self-assembly of an isatin-thiazoline
hybrid, Journal of Molecular Structure (2015), doi: 10.1016/j.molstruc.2015.06.013.
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ACCEPTED MANUSCRIPT
Synthesis and fluorine-mediated interactions in methanol-encapsulated solid
state self-assembly of an isatin-thiazoline hybrid
Humayun Perveza, Maqbool Ahmada, Taibi B. Haddab, Loic Toupetc, Muhammad Moazzam
Naseerd*
a Institute of Chemical Sciences, Organic Chemistry Division, Bahauddin Zakariya University, Multan 60800,
Pakistan
b Laboratoire de Chimie des Matériaux (LCM), Faculté des Sciences d’Oujda (FSO), Université Mohammed 1Er,
60000-Oujda, Morocco
c Institut de Physique de Rennes, UMR 625, Université de Rennes 1, Campus de Beaulieu Bat. 11 A, 263 av. Général
Leclerc, 35042 Rennes Cedex, France
d Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan
ABSTRACT: An exciting isatin-thiazoline hybrid molecule 2 having -C=N-N=C- linkage has
been synthesized in 88% yield by the reaction of 5-fluoroisatin with N-(4-
fluorophenyl)hydrazinecarbothioamide followed by condensation of the resultant isatin-
thiosemicarbazone intermediate with p-chlorophenacyl bromide. The solid state self-assembly of
this hybrid molecule was studied by X-ray crystallographic technique. A layered assembly
composed of 1D-chains with methanol molecules encapsulated between every two chains is
obtained, making a bi-chain sandwich like structure. The supramolecular forces involved in the
stabilization of this structure are importantly fluorine-mediated interactions (C-H···F, F···S and
F···π) along with others i.e. N-H···O, O-H···O, C-H···O, Cl···π, C-H···π and π···π interactions.
To the best of our knowledge, this is the first example of solid state fluorine-mediated C-H···F,
F···S and F···π interactions found in a family of isatin-based compounds.
Keywords: isatin-thiazoline hybrid; synthesis; self-assembly; fluorine-mediated interactions;
layered structure
*Corresponding authors. tel.: +92 51 90642129; fax:+92 51 90642241 (M.M.N.).
E-mail addresses: moazzam@qau.edu.pk (M.M. Naseer), pdhpervez@hotmail.com (H. Pervez).

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1. Introduction
Weaker hydrogen bonds of the C-H···X-C type play an important role in the stabilization of
crystal structures. Hence, the C-H···O, C-H···N, and C-H···Cl hydrogen bonds have
increasingly been used in crystal engineering [1-11]. However, the interactions involving
“organic fluorine” i.e. C-H···F interactions have always been a controversial subject in
contemporary research and their nature still remains obscure [12-17]. According to Pauling’s
definition of the hydrogen bond, F atom should be a stronger hydrogen bond acceptor than O and
N atoms due to its high electronegativity [18]. But practically, it does not form hydrogen bonds
commensurate with electronegativity considerations and has been considered as a very poor
acceptor in supramolecular chemistry [14]. Recently, this interaction was evaluated by ab initio
calculations and found to be much more important in defining the crystal packing than portrayed
earlier [19].
In addition to C-H···F interactions, F···X (X=S, π) interactions are the other relatively weak
interactions that have recently been recognized in organic fluorinated molecules [20-24]. It is
now well-established that drug molecules containing one or more fluorine atoms show superior
biological properties as compared to their non-fluorinated analogues perhaps due to better
interactions with the receptor sites in our body [25]. Because of its small size, fluorine is also an
ideal substituent where change in the electronic properties of the molecules is needed without
affecting the steric environment. Furthermore, its lipophilic character also plays an important
role in increasing the bioavailability of fluorinated drug molecules [26]. Therefore, more efforts
are necessary for appropriate understanding of the intermolecular interactions offered by the
fluorine atom.

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Isatin (indole-1H-2,3-dione) is undoubtedly a privileged scaffold for chemical modification
due to its presence in a number of naturally occurring substances [27,28]. Although, a number of
its derivatives have been prepared through electrophilic aromatic substitution at positions C-5
and C-7 of the phenyl ring and by N-substitution, but the most important and fascinating site for
the purpose is C-3 carbonyl group due to its high reactivity with various nucleophiles. It
generally undergoes nucleophilic addition or spiroannulation at this position, providing a broad
range of 2-oxindole derivatives of immense biological importance [27,28]. Furthermore, isatin is
structurally an ideal candidate to serve as a highly variable tecton for the construction of
supramolecular assemblies due to its remarkable hydrogen bond donor/acceptor abilities and a
relatively large molecular dipole moment [29-31]. Keeping this in view, we very recently
reported the synthesis and solid state self-assembly of 5-fluoroisatin-based hybrid molecule 1,
where no intermolecular interactions were observed for fluoro substituent in the presence of N-
H···O, C-H···O, C-H···N, C-H···π, π···π, C-H···Cl interactions [32]. This observation and our
continuous interest in supramolecular self-assemblies [33-39] increased our curiosity and
prompted us to introduce 4-fluoro group as a substitute to 3-methoxy on the central N-aryl ring
of the rigid core of isatin-thiazoline hybrid 1 to explore the existence of fluorine-mediated
interactions in isatin-based compounds. Pleasingly, the approach remained successful and herein,
we report the synthesis and methanol-encapsulated layered assembly of isatin-thiazoline hybrid 2
with unprecedented C-H···F, F···S and F···π interactions in a vast library of isatin-based
compounds. In addition, this also represents one of the rare examples of fluorine-mediated
interactions found in the presence of other strong non-covalent interactions reported so far [40-
42].

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Figure 1. Molecular structures of isatin-thiazoline hybrids 1 and 2
2. Experimental
2.1 Materials and Methods
All regents and solvents were used as obtained from the supplier or recrystallized or redistilled as
necessary. Thin layer chromatography (TLC) using glass plates coated with Silica gel 60 GF254
(E.Marck) was performed to check the progress of the reaction and the purity of the product. The
spots were visualized under ultraviolet light at 254 and 366 nm and / or spraying with iodine
vapours. Melting point was taken on a Fisher-Johns melting point apparatus and is uncorrected.
Elemental analysis was performed on a Leco CHNS-9320 elemental analyzer. Infrared spectrum
1
(KBr disk) was run on Shimadzu 8400. H-NMR spectrum was recorded in C2D6SO on Bruker
(Rhenistentten-Forchheim, Germany) AM 300 spectrometer operating at 300 MHz, using TMS
1
as an internal standard. H chemical shifts are reported in (ppm) and coupling constants in Hz.
Mass spectrum was recorded on agilent 6310 ion trap LC/MS mass spectrometer.
Procedure for the preparation of (3Z)-5-fluoro-1H-indole-2,3-dione 3-{[(2Z)-4-(4-
chlorophenyl)-3-(4-fluorophenyl)-1,3-thiazol-2(3H)-ylidene]hydrazone} (2)

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To a solution of 5-fluoroisatin (0.01 mol) in 50% aqueous EtOH (20 mL) containing a catalytic
amount of glacial AcOH was added an ethanolic solution (20 mL) of N-(4-
fluorophenyl)hydrazinecarbothioamide (0.01 mol) with constant stirring. The reaction mixture
was then refluxed for 2 h. The solid obtained during refluxing was collected by suction filtration.
Thorough washing with hot aqueous EtOH (50%) afforded the desired thiosemicabazone, which
was used as such without further purification [43]. The synthesized thiosemicabazone (0.005
mol) was subsequently mixed with p-chlorophenacyl bromide (0.005 mol) in absolute EtOH (25
mL) and heated under reflux for 15 h. The refluxate was concentrated on rotary evaporator and
the precipitate thus formed was filtered. Thorough washing with n-hexane followed by
crystallization from water/ethanol furnished the target compound 2 in pure form. The synthesized
compound 2 is characterized as follows:
Yield 88% as orange yellow crystals; m.p. 298-300 °C; IR (KBr, cm-1): 3177 (NH stretching),
1
1705 (C=O), 1624 (C=N); H-NMR (DMSO-d6, δ, ppm): 6.75 (dd, J = 8.7, 4.5 Hz, 1H, indole
C7-H), 7.03 (td, J = 9.3, 2.7 Hz, 1H, indole C6-H), 7.09 (dd, J = 9.0, 2.7 Hz, 1H, indole C4-H),
7.11 (s, 1H, thiazoline =CH), 7.29 (d, J = 8.7 Hz, 2H, phenyl C2-H, C6-H), 7.37 (t, J = 8.7 Hz,
2H, N- phenyl C2-H, C6-H), 7.41 (d, J = 8.7 Hz, 2H, phenyl C3-H, C5-H), 7.55 (dd, J = 8.7, 4.5
Hz, 2H, N-phenyl C3-H, C5-H), 10.50 (s, 1H, indole NH); EIMS (70eV) m/z (%): 468 (M ++ 2,
75), 467 (M+ + 1, 55), 466 (M+, 100), 440 (8), 439 (9), 438 (18), 437 (11), 305 (6), 304 (8), 303
(12), 292 (35), 291 (19), 290 (82), 288 (22), 234 (7), 232 (16), 170 (8), 168 (19), 153 (26), 149
(13), 136 (9), 134 (7), 133 (6), 121 (12), 108 (6), 95 (14), 75 (7); Anal calcd. for
C23H13ClF2N4OS: C 59.16, H 2.79, N 12.00; found: C 59.16, H 2.77, N 11.99.
2.2. Crystallographic data collection and structure refinements

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Suitable X-ray quality crystals of compound 2 were obtained by slow evaporation of its solution
in dichloromethane-methanol solvent mixture at ambient temperature. Single crystal X-ray
structural studies of 2 were performed on a CCD Oxford Diffraction XcaliburSaphir 3
diffractometer, employing graphite-monochromated Mo-Kα radiation generated from a fine-
focus sealed tube (λ = 0.71073Å) at 150(2) K. Data collection strategy was evaluated by using
the CrysAlisPro CCD software. Collections of data were observed by the standard ω scan
techniques and were scaled and reduced using CrysAlisPro RED software. The structure was
solved by direct methods using SIR-97 [44] and refined by least–squares methods on F2 using
SHELXL-97 [45]. The positions of all the atoms were obtained by direct methods. Anisotropic
thermal parameters were assigned to all non–hydrogen atoms and the remaining hydrogen atoms
were placed in geometrically constrained positions and refined as riding atoms with a common
fixed isotropic thermal parameter. The drawing of the complex was realized with PLATON [46].
A summary of the selected crystallographic information is given in Table 1.
Table 1. Crystal data and structure refinement for 2
Crystal data
CCDC
2
981215
Chemical formula
Mr
C24H17ClF2N4O2S
498.93
Crystal system, space group
Temperature (K)
a, b, c (Å)
Monoclinic, P21/c
150
9.6361 (4), 10.6068 (3), 22.6225 (7)
97.549 (3)
2292.16 (14)
4
β
(°)
V (Å3)
Z
Radiation type
Mo K
α
(mm-1)
0.30
µ

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Crystal size (mm)
Data collection
Diffractometer
0.29 × 0.19 × 0.13
CCD Saphire 3 Xcalibur
diffractometer
Absorption correction
–
No. of measured, independent and
19330, 5008, 4183
observed [I> 2σ(I)] reflections
Rint
0.032
0.639
(sin
Refinement
R[F2> 2 (F2)], wR(F2), S
θ/λ)
max (Å-1)
0.033, 0.086, 1.02
σ
No. of reflections
No. of parameters
H-atom treatment
5008
308
H-atom parameters constrained
0.30, -0.27
∆〉
, ∆〉
min (e Å-3)
max
3. Results and discussion
As depicted in Scheme 1, isatin-thiazoline hybrid molecule 2 was synthesized by reacting 5-
fluoroisatin with one equivalent of N-(4-fluorophenyl)hydrazinecarbothioamide in ethanol
solvent containing a catalytic amount of glacial acetic acid in the first step and then treating the
resultant product dissolved in absolute ethanol with 4-chlorophenacyl bromide at reflux
temperature in the second step.

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Scheme 1. Synthesis of isatin-thiazoline hybrid molecule 2
Single crystals of 2, suitable for X-ray analysis (Figure 2, Table 1) were cultivated in a
dichloromethane/methanol solvent mixture by slow evaporation method and found to have a
monoclinic crystal lattice with the P21/c space group. It is important to mention here that these
are the same conditions for crystal growth as used previously for compound 1 [32]. In this
compound, isatin and the central thiazoline rings that are connected with each other through -
C=N-N=C- linkage lie nearly in the same plane. However, the two aryl rings substituted on
thiazoline moiety are tilted as compared to the plane of isatin-thiazoline rings. The fluoro-
substituted aryl ring present at N4-of the thiazoline moiety is positioned in such a way that H5 of
the isatin is located on almost top and the centre of its aromatic ring plane with a distance of
2.977 Å. The dihedral angle between the plane of fluoro-substituted aryl and thiazoline rings is

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69.67° (C9-N4-C18-C19). The chloro-substituted aryl ring at C-10 of the thiazoline ring is less
tilted as compared to the N4-aryl one with a dihedral angle of 42.06° (N4-C10-C12-C17) from
the isatin-thiazoline plane. In the thiazoline ring, the S(1)-C(9) and S(1)-C(11) bond lengths are
1.733(14) Å and 1.735(15) Å, respectively, with the C(9)-S(1)-C(11) bond angle being
90.10(7)°. Other selected bond lengths and bond angles are presented in the caption to figure 2.
The most significant and interesting feature of this compound is its molecular packing in the
solid state, stabilized by fluorine-mediated interactions (C-H···F, F···S and F···π) (Figure 3) in
addition to other non-covalent interactions (N-H···O, O-H···O, C-H···O, Cl···π, C-H···π, π···π)
(Table 2). The crystal structure revealed methanol-encapsulated layered assembly, composed of
1D-supramolecular chains (Figure 4). As shown in figures 4a & 4b, methanol molecules are
sandwiched between every two chains of a layer. Each 1D-chain of this assembly is formed by
the lateral arrangement of molecules by means of F···S [F(1)···S(1) 3.014 Å] and F···π [F(1)
···C(11) 3.123 Å] interactions. The molecules in every chain of a layer with respect to another
are inverted. Two neighbouring chains, which are encapsulating the methanol molecules by
means of mainly N-H···O [N(1)-H(1)···O(2) 1.981 Å], O-H···O [O(2)-H(2A)···O(1) 1.871 Å]
and C-H···O [C(3)-H(3)···O(2) 2.521 Å] interactions, are connected with each other through C-
H···O [C(2)-H(2)···O(1) 2.448 Å] interactions. The two consecutive chains, which are
sandwiching the methanol molecules (a bi-chain sandwich) are connected to the next bi-chain
sandwich with the help of Cl···π [Cl(1)···C(20) 3.406 Å, Cl(1)···C(21) 3.261 Å] interactions.
Furthermore, each layer of this assembly is connected to the next layer by means of C-H···F
[C(22)-H(22)···F(1) 2.597 Å], C-H···π [C(24)-H(24)···C(15) 2.876 Å, C(20)-H(20)···C(3) 2.828
Å], C-H···O [C(17)-H(17)···O(1) 2.601 Å] and π···π [C(9)···N(2) 3.232 Å] interactions between
anti-parallel stacked molecules of 2, providing an overall multi-layered structure (Figure 4c).

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Figure 2. X-ray crystal structure of 2. Selected bond lengths (Å): Cl(1)-C(15) 1.373(16); S(1)-
C(9) 1.733(14); S(1)-C(11) 1.735(15); F(1)-C(4) 1.368(17); F(2)-C(21) 1.360(18); O(1)-C(8)
1.230(18); N(1)-C(8) 1.356(19); N(1)-C(1) 1.405(19); N(1)-H(1) 0.8800; N(2)-C(7) 1.298(19);
N(2)-N(3) 1.363(16); N(3)-C(9) 1.309(18); N(4)-C(9) 1.369(18); N(4)-C(10) 1.406(18); N(4)-
C(18) 1.443(17). Selected bond angles (°): C(9)-S(1)-C(11) 90.10(7); C(8)-N(1)-C(1)
111.25(12); C(7)-N(2)-N(3) 111.95(12); C(9)-N(3)-N(2) 111.84(12); C(9)-N(4)-C(10)
113.78(11); C(9)-N(4)-C(18) 118.44(11); C(10)-N(4)-C(18) 127.76(11).
Figure 3. Crystal packing of 2 highlighting fluorine-mediated C-H···F, F···S and F···π
interactions

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Table 2. Non-covalent interactions stabilizing the methanol-encapsulated solid state self-
assembly of compound
2
Interaction type
C-H···F
F···S
Atoms involved
C(22)-H(22)···F(1)
C(4)-F(1)···S(1)
C(4)-F(1) ···C(11)
N(1)-H(1)···O(2)
O(2)-H(2A)···O(1)
C(3)-H(3)···O(2)
C(2)-H(2)···O(1)
C(17)-H(17)···O(1)
C(24)-H(24)···C(15)
C(20)-H(20)···C(3)
Cl(1)···C(20)
Distance (Å)
2.597
3.014
3.123
1.981
1.871
2.521
2.448
2.601
2.876
2.828
3.406
3.261
3.232
F···π
N-H···O
O-H···O
C-H···O
C-H···π
Cl···π
π···π
Cl(1)···C(21)
C(9)···N(2)
(a)

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(b)
(c)
Figure 4.Crystal packing of compound 2: a) view of four neighbouring 1D-chains having
methanol molecules encapsulated between two chains forming a bi-chain methanol sandwich
along a-axis; b) view of a layer along b-axis; c) view of two consecutive layers along b-axis
To the best of our knowledge, fluorine-mediated C-H···F, F···S and F···π interactions described
here have not been reported so far in a family of isatin-based compounds. It is worth mentioning
that C-H···O interactions observed in
outweighed by the fluorine-mediated interactions found in the present case [32]. The
introduction of fluoro substituent as a substitute to methoxy on the central aryl ring of led to
1 due to the presence of methoxy substituent are
2
the appearance of fluorine-mediated interactions. The strategy to observe fluorine-mediated
interactions used here could possibly be used in other rigid systems to explore and understand
their positive effects on the biological properties of a specific drug molecule, in addition to their
applications in crystal engineering field [47].
4. Conclusions
In summary, we have synthesized an interesting isatin-thiazoline hybrid molecule 2 and studied
its solid state self-assembling behaviour by X-ray crystallography. A multi-layered methanol
encapsulated network assembly, which is composed of various 1D-chains, has been observed.
Fascinatingly, methanol molecules are sandwiched between two 1D-chains of this assembly. The

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notable supramolecular interactions involved in the stabilization of this assembly are C-H···F,
F···S and F···π, which were not only absent in our previously reported isatin-thiazoline hybrid
1
but also, to the best of our knowledge, never reported earlier in the family of isatin-based
compounds by other workers. As illustrated in the present example and also revealed from our
previous study and the literature survey, fluorine-mediated interactions may occur even in the
presence of other strong non-covalent interactions but it depends largely on the geometry of the
molecules. Furthermore, they are not very weak interactions (C-H···F = 2.597 Å) and may have
significant ability to direct the molecular packing, which highlights their much larger role in the
crystal packing than anticipated so far [47]. The general perception that organic fluorine hardly
ever accepts hydrogen bond [14] has been found to gradually change during the past two decades
and its structure directing role is now recognized [16]. However, to understand its role in biology
and use as a reliable synthon in crystal engineering still needs more research.
Acknowledgments
We acknowledge partial funding of this research work and the award of indigenous PhD
scholarship to MA by Higher Education Commission (HEC), Government of Pakistan.
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self-assembly of an isatin-thiazoline hybrid driven by three self-complementary dimeric
motifs, Tetrahedron Lett, 55 (2014) 5400-5403.

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Research Highlights:
ꢀ An isatin-thiazoline hybrid molecule having -C=N-N=C- linkage has been synthesized.
ꢀ Solid state self-assembly was studied by X-ray crystallographic technique.
ꢀ A bi-chain sandwich like structure with methanol molecules encapsulated between every
two chains is obtained.
ꢀ Fluorine-mediated interactions are involved in the stabilization of this assembly.

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checkCIF/PLATON report
You have not supplied any structure factors. As a result the full set of tests cannot be run.
THIS REPORT IS FOR GUIDANCE ONLY. IF USED AS PART OF A REVIEW PROCEDURE
FOR PUBLICATION, IT SHOULD NOT REPLACE THE EXPERTISE OF AN EXPERIENCED
CRYSTALLOGRAPHIC REFEREE.
No syntax errors found.
CIF dictionary
Interpreting this report
Datablock: shelx
Bond precision: C-C = 0.0021 A
Wavelength=0.71073
Cell:
a=9.6361(4)
alpha=90
150 K
b=10.6068(3)
beta=97.549(3)
c=22.6225(7)
gamma=90
Temperature:
Calculated
Reported
Volume
Space group
Hall group
2292.17(14)
P 21/c
-P 2ybc
2292.16(14)
P 21/c
-P 2ybc
C23 H13 Cl F2 N4 O S, C H4
O
Moiety formula
?
Sum formula
Mr
Dx,g cm-3
Z
C24 H17 Cl F2 N4 O2 S
498.93
1.446
C24 H17 Cl F2 N4 O2 S
498.92
1.446
4
4
Mu (mm-1)
F000
F000’
h,k,lmax
Nref
0.304
0.304
1024.0
1024.0
1025.55
12,13,28
5012
12,13,28
5008
Tmin,Tmax
Tmin’
0.933,0.961
0.917
Correction method= Not given
Data completeness= 0.999
Theta(max)= 26.997
wR2(reflections)= 0.0864( 5008)
R(reflections)= 0.0333( 4183)
S = 1.022
Npar= 307
The following ALERTS were generated. Each ALERT has the format
test-name_ALERT_alert-type_alert-level.
Click on the hyperlinks for more details of the test.

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Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. #
C23 H13 Cl F2 N4 O S
1 Note
Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............
PLAT169_ALERT_4_G The CIF-Embedded .res File Contains AFIX 1 Recds
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. #
C H4 O
2 Report
2 Report
2 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
3 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
It is advisable to attempt to resolve as many as possible of the alerts in all categories. Often the
minor alerts point to easily fixed oversights, errors and omissions in your CIF or refinement
strategy, so attention to these fine details can be worthwhile. In order to resolve some of the more
serious problems it may be necessary to carry out additional measurements or structure
refinements. However, the purpose of your study may justify the reported deviations and the more
serious of these should normally be commented upon in the discussion or experimental section of a
paper or in the "special_details" fields of the CIF. checkCIF was carefully designed to identify
outliers and unusual parameters, but every test has its limitations and alerts that are not important
in a particular case may appear. Conversely, the absence of alerts does not guarantee there are no
aspects of the results needing attention. It is up to the individual to critically assess their own
results and, if necessary, seek expert advice.
Publication of your CIF in IUCr journals
A basic structural check has been run on your CIF. These basic checks will be run on all CIFs
submitted for publication in IUCr journals (Acta Crystallographica, Journal of Applied
Crystallography, Journal of Synchrotron Radiation); however, if you intend to submit to Acta
Crystallographica Section C or E, you should make sure that full publication checks are run on the
final version of your CIF prior to submission.
Publication of your CIF in other journals
Please refer to the Notes for Authors of the relevant journal for any special instructions relating to
CIF submission.
PLATON version of 21/04/2015; check.def file version of 09/03/2015

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Datablock shelx - ellipsoid plot