Fluorine-fluorine type II versus πF-π stacking interactions in the supramolecular organizations of extended thiophene derivatives end capped by imino-perfluorophenyl units

Article abstract of DOI:10.1016/j.jfluchem.2015.06.018

Abstract The solid state arrangements of extended thiophene derivatives associating pentafluorophenyl units linked via azomethine bonds are analyzed in terms of intermolecular interactions involving hydrogen and halogen bonds and π-π_F interacti

Full text of DOI:10.1016/j.jfluchem.2015.06.018

Journal of Fluorine Chemistry 178 (2015) 34–39
Contents lists available at ScienceDirect
Journal of Fluorine Chemistry
journal homepage: www.elsevier.com/locate/fluor
Fluorine–fluorine type II versus pF–p stacking interactions in the
supramolecular organizations of extended thiophene derivatives
end capped by imino-perfluorophenyl units
*
´ ´
`
Chady Moussallem, Magali Allain, Charlotte Mallet, Frederic Gohier, Pierre Frere
Universite´ d’Angers, MOLTECH-Anjou, UMR CNRS 6200, 2 boulevard Lavoisier, 49045 Angers cedex, France
A R T I C L E I N F O
A B S T R A C T
Article history:
The solid state arrangements of extended thiophene derivatives associating pentafluorophenyl units
linked via azomethine bonds are analyzed in terms of intermolecular interactions involving hydrogen
Received 20 March 2015
Received in revised form 17 June 2015
Accepted 19 June 2015
and halogen bonds and
systems, the structure is driven by FÁ Á ÁF type II contacts giving orthogonal disposition while the
lengthening of the conjugated backbone favors parallel arrangements via pF interactions.
pÀpF interactions. It is shown that in the presence of the shortest conjugated
Available online 25 June 2015
pÀ
ß 2015 Elsevier B.V. All rights reserved.
Keywords:
Pentafluorophenyl unit
Aryl–perfluoroaryl interactions
Halogen bonds
Azomethine bonds
Conjugated systems
1. Introduction
are only a consequence of the stacking mode in the solid [21].
Generally the FÁ Á ÁF contacts are type I and it is admitted that the
FÁ Á ÁF interactions do not participate in the supramolecular
organization of the solid. Nevertheless it was demonstrated that
when pentafluorophenyl or tetrafluorophenyl units were com-
bined with acceptor groups, FÁ Á ÁF type II interactions could
intervene in the packing of the molecules in the crystal [22]. In
the field of organic semiconducting materials, the insertion of
perfluorophenyl units in conjugated systems has been exploited to
control the electronic affinity and/or the packing mode of the
conjugated backbone and thus to tune the electronic properties of
the materials [3,4,23–27].
The discovery of the benzene–perfluorobenzene co-crystalliza-
tion by Patrick and Prosper [1] initiated numerous studies aiming
at a better understanding of the intermolecular interactions
involved between aryl and perfluoroaryl groups [2–9]. Although
the various factors that determine the role of the fluorine atoms in
the intermolecular interactions are not yet fully mastered, several
types of interactions can be considered: (i)
p pF interactions
À
between aryl and perfluoroaryl units that contribute to favor the
stacking of the molecules in the materials, (ii) hydrogen bonds
C–FÁ Á ÁH–C that favor the lateral contacts and can also contribute to
strengthen the pi-stacking, (iii) C–FÁ Á Á
p
F contacts induced by the
We have reported on the structural features of Donor–Acceptor–
Donor type conjugated materials associating furan or thiophene
cycles linked via azomethine bonds to pentafluorophenyl units
[28,29]. We showed that the imino-perfluorophenyl units drive the
polarization of the C–F bond and by the character globally positive
in the center of the aromatic C6F5 ring, and (iv) FÁ Á ÁF halogen bonds
[5,9–16]. Owing to the small polarizability of the fluorine atoms,
the FÁ Á ÁF contacts should be weak and do not have any influence on
the stacking mode in the crystal. Ramasubbu et al. classified the
halogen bonds in two types depending on the angles u1 and u2
packing modes in the solids via subtle balance between
pÀp and
donor–acceptor interactions. The preponderant roles of these
intermolecular interactions were strongly dependent on the nature
of the heterocycle and on the extended systems used as a spacer
between the two external pentafluorophenyls units. In our
continuing effort of studying the role of the imino-perfluorophenyl
units on the stacking mode of hybrid heterocycle–perfluorophenyl
structures, we report here on the structural features of the extended
compounds 1–3. We show that the structures are entirely driven by
intermolecular interactions induced by the external phenyl or
adopted between the C–XÁ Á ÁX–C bonds (Fig. 1): type I when u1
ꢀ
u2
and type II when u1 ꢀ 1808 and u2 ꢀ 908 [17–20]. The interactions
of type II are considered as stabilizing while the type I interactions
*
Corresponding author. Tel.: +33 241735063.
E-mail address: pierre.frere@univ-angers.fr (P. Fre`re).
http://dx.doi.org/10.1016/j.jfluchem.2015.06.018
0022-1139/ß 2015 Elsevier B.V. All rights reserved.

C. Moussallem et al. / Journal of Fluorine Chemistry 178 (2015) 34–39
35
the ethylenic bonds of 3 is demonstrated by the 15.6 Hz constant
coupling in the 1H NMR signal of the ethylenic bonds (Fig. S1 in
supplementary data).
Electronic properties of compounds 1–3 have been analyzed by
UV–vis spectroscopy and by cyclic voltammetry (CV) (Table 1). The
UV–vis absorption spectra of compounds 1–3 in CHCl3 exhibit
broad band absorption bands (Fig. S2). Compounds 1 and 2 present
maxima wavelength at 375 and 370 nm. The blue shift observed for
2 compared to 1 corresponds to an increase of the torsional angle of
Fig. 1. The two types of halogen bonds.
the azomethine bonds (F) with perfluorophenyl units (vide infra).
As expected, the extension of the conjugated systems for 3
provokes a bathochromic shift of the absorption bands to reach a
lmax of 410 nm. The three compounds present an irreversible
oxidation process respectively at 1.34, 1.52 and 1.28 V correspond-
ing to the formation of a radical cation (Figs. S3–S5). Moreover 3
shows a second irreversible oxidation wave at 1.51 V due to the
oxidation of 3+ꢁ in dication 3++. The extension of the conjugated
systems by polyene units is known to favor the access to the
dication state by decreasing the Coulombic repulsion between the
positive charges. In reduction compounds 1–3 presents an
irreversible wave respectively at À1.40, À1.30 and À1.32 V. The
replacement of the phenyl by perfluorophenyl units between 1 and
2 increase the electron acceptor character leading to a rise both of
oxidation and reduction potentials. The insertion of ethylenic
bonds for 3 gives a modest effect on the reduction potential
indicating that the electron acceptor character is mainly due to the
iminoperfluorophenyl units [36,37].
Single crystals suitable for X-ray diffraction analysis are
obtained for compounds 1–3 by slow evaporation of chloro-
form–ethanol solutions.
Compound 1 crystallizes in the monoclinic space group C2/c.
The structure is defined from a half molecule which lies on a
twofold axis. As shown in Fig. 2a, compound 1 has an E–E
configuration for the azomethine junctions that present also a
perfluorophenyl units without any participation of the central
thiophene cycle. Moreover depending on the length of the
conjugated systems, a competition occurs between FÁ Á ÁF interac-
tions of type II and pF–p stacking interactions.
2. Results and discussion
Compounds 1–3 were synthesized by condensation of 2,5-
dicarbaldehyde thiophene 4 and 2,5-bis(3-oxo-1-propenyl)thio-
phene 5 with aniline or pentafluoroaniline (Scheme 1). Dialdehyde
5 was prepared by Wittig oxopropenylation with 1,3-dioxan-2-
ylmethyltributylphosphorane on
4 [30]. Compound 1 was
obtained by adding an excess of aniline to aldehyde 4 without
solvent at room temperature [31]. The exothermic reaction led to a
yellow solid which was washed with methanol to give 1 in 90%
yield. Compounds 2 were obtained by condensation of aldehyde 4
and pentafluoroaniline in ethyl lactate as solvent at room
temperature with a little amount of P2O5 (ꢀ5 mol%) [32–35].
After 8 h stirring the mixture was poured in a water–methanol
solution (50–50 vol.) to give a yellow precipitate. The solid was
recrystallized from ethanol solution to give 2 in 70% yield. The
same protocol with aldehyde 5 yielded compound 3 in small yield
of 15%. The synthesis of compound 3 was also tested using
microwave irradiation with a catalytic amount of P2O5 (10 mol%) in
dichloromethane [28]. This method allowed to obtain 3 in 55%
yield after chromatography on silica gel. The E–E configuration of
d
-syn configuration with the nitrogen atoms pointing in the same
direction of sulfur atom. Such configuration of extended thiophene
derivatives are often observed [38,39]. The lateral phenyl rings are
not coplanar with the central conjugated system assuming a
NH2
S
1
no solvent
N
N
+ 2
+ 2
OHC
OHC
CHO
CHO
S
4
NH2
F
F
F
F
S
F
F
F
F
F
Ethyl lactate
N
N
2
P2O5 (5% mol)
S
4
F
F
F
F
F
F
F
O
O
1)
Br
PBu3
MeONa, MeOH
2) CHCl3, HCl
S
F
NH2
F
F
F
F
F
F
N
3
N
CHCl3
P2O5 (10% mol)
microwave
S
5
+ 2
CHO
F
F
OHC
F
F
F
F
F
Scheme 1. Synthesis of compounds 1–3.

36
C. Moussallem et al. / Journal of Fluorine Chemistry 178 (2015) 34–39
Table 1
same E–E configuration as 1 with a torsion angle between the
perfluorophenyl rings and the imine bonds increasing to 458
(Fig. 3a). As shown in Fig. 3b, the molecules stack along the b axis
Torsional angle of azomethine bondsa, electronic absorptionb and cyclic voltam-
metry datac of compounds 1–3.
Compound
F
/(8)
lmax/nm
Eox1/V
Eox2/V
Ered1/V
with
a juxtaposition of the thiophene cycles but without
presenting any
p
À
p
interactions. Indeed the distance separating
˚
1
2
3
358
458
358
375
370
410
1.34
1.52
1.28
–
À1.45
À1.30
À1.32
–
two planes defined by the thiophene cycle is of 3.83 A with a SÁ Á ÁS
1.51
˚
distance of 4.286(2) A. The packing mode is defined by C–FÁ Á Á
pF
a
Calculated from the X-ray structure.
10À5 M in CHCl3.
10À3 M in 0.1 M Bu4NPF6/CH2Cl2, v = 200 mV/s, reference AgCl/Ag.
interactions between pentafluorophenyl rings that present a face
to face arrangement with a slight shift allowing a fluorine atom to
superimpose the center of the aromatic ring (Fig. 3c). The distance
b
c
˚
separating two benzene cores is of 3.2 A. Between the columns of
molecules, the structure exhibits type II FÁ Á ÁF contacts with short
˚
distances dFÁ Á ÁF = 2.836(4) A and angles of
u
1 = 86.78 and
u
2 = 156.38
torsional angle of 358 with respect to the thiophene cycle. The
structure is iso-structural to the one obtained for furan analog [28].
The packing of the molecules is mainly defined by C–HÁ Á ÁPh
interactions between the external phenyl cycles that present an
edge to face arrangement (Figs. 2b and c). Such interactions lead to
a stacking of the molecules along the c axis in a head to tail mode
which strongly limits the contacts between the conjugated
systems. As shown in Fig. 2c, the planes defined by the thiophene
(purple dotted lines in Figs. 3b and c) leading to quasi orthogonal
arrangement between the two perfluorophenyl units. Moreover
the contacts inter column are complemented by HÁ Á ÁF contacts
involving hydrogen atoms of the thiophene cycles with distances
˚
dHÁ Á ÁF = 2.70(7) A (orange dotted lines in Fig. 3b) and habitual type I
˚
˚
FÁ Á ÁF contacts with distances of 2.852(5) A and 2.881(5) A (green
dotted lines in Fig. 3b). By contrast with furan derivatives for which
furan–perfluorophenyl interactions were observed, here there is
˚
cycles are parallel and equidistant of 3.593(2) A. There are few
no p-interaction between the thiophene and perfluorophenyl
contacts between the thiophene cycles, the shortest distance
between two atoms implying sulfur and carbon atoms of two
cycles for participating to the supramolecular organization.
Compound 3 crystallizes in the monoclinic space group C2/c.
The structure is defined from a half molecule which lies on a
twofold axis. The structure confirms the E–E configuration for the
ethylenic protons and shows an E–E configuration for the imine
bonds (Fig. 4a). The ethylenic and the imine bonds are in the plane
defined by the central thiophene cycle while the external
pentafluorophenyl groups present a torsional angle of 358 with
the imine bonds.
˚
adjacent thiophene cycles is of 3.601(2) A. On the other hand, there
is not any contact along the a and b axes between the columns of
molecules.
Compound 2 crystallizes in the monoclinic space group Cc. The
replacement of hydrogen atoms by fluorine atoms provokes a
strong modification of the packing mode while the molecular
structure is not strongly modified. The molecule 2 presents the
Fig. 2. X-ray structure of 1. (a) Molecular structure of 1 with anisotropic displacement ellipsoid drawn at 50% probability level. (b) Crystal packing of 1 viewed along the c axis.
(c) Stacking mode of molecules along the c axis, C–HÁ Á ÁPh interactions are shown in red dotted lines. (For interpretation of the references to color in this figure legend, the
reader is referred to the web version of this article.)

C. Moussallem et al. / Journal of Fluorine Chemistry 178 (2015) 34–39
37
Fig. 3. X-ray structure of 2. (a) Molecular structure of 2 with anisotropic displacement ellipsoid drawn at 50% probability level. (b) Crystal packing of 2 viewed along b axis, C–
FÁ Á ÁH–C contacts are presented in orange dotted lines and the type I FÁ Á ÁF contacts in green dotted lines. (c) Stacking mode of molecules along the b axis showing the type II
FÁ Á ÁF contacts (purple dotted lines). (For interpretation of the references to color in this figure legend, the reader is referred to the web version of this article.)
The lengthening of the conjugated systems by the incorporation
of ethylenic bonds between the central thiophene core and the
3. Experimental
external iminoperfluorophenyl units leads to increase the
p
3.1. Synthesis
contacts in the packing mode. As shown in Fig. 4b, the structure is
built by some ribbons of molecules oriented along the c axis which
stack along the a axis. The ribbons are linked themselves by
Dialdehyde derivatives 4 [40] and 5 [30] were synthesized as
already described.
˚
C–HÁ Á ÁF contacts with distances dHÁ Á ÁF = 2.523(3) A (dotted orange
line in Fig. 4b). Along the a axis, the molecules overlap by
presenting an arrangement in which each molecule is in close
contacts with four molecules, two below and two above (Fig. 4c).
The short contacts are essentially due to interactions between
carbon and fluorine atoms of the perfluorophenyl cycles and
carbon and nitrogen atoms of the conjugated systems with
3.1.1. 2,5-Bis(phenyliminomethyl)thiophene 1 [31]
A slight excess of aniline was added to an erlenmeyer of 25 mL
containing 1.0 g of dialdehyde 4 (7.1 mmol) at room temperature.
The temperature rapidly raised thus allowing the liberation of
vapor water. After 10 min, the brown solid obtained was purified
by adding 3 mL of methanol. The solid was recovered by filtration,
washed with 2 mL of methanol and dried in vacuo to give 1.9 g of
compound 1 (90% yield).
˚
interatomic distances ranging between 3.179(7) and 3.456(6) A
as shown by blue dotted lines in Fig. 4c. Thus the stacking mode in
compound 3 mainly implicates pF
contacts.
In conclusion this comparative structural study between the
–
p
interactions combined with
Yellow pale solid, Mp = 204–206 8C.
p
À
p
1H NMR (CDCl3): 8.58 (s, 2H), 7.50 (s, 2H), 7.43–7.38 (m, 4H),
7.28–7.24 (m, 6H).
compounds 1–3 well shows the primordial role of the external
imino-perfluorophenyl groups to organize the packing arrange-
ments in the crystals. The shortest structure 2 is dominated by
FÁ Á ÁF type II contacts completed by C–FÁ Á ÁpF interactions. Such
13C NMR (CDCl3): 152.5, 151.1, 146.5, 131.9, 129.4, 126.8, 121.3.
MS Maldi-tof: calcd. for C18H14SN2 (M + H) 291.0956; found
291.0957.
Elemental analysis for C18H14SN2: calcd. C 74.45, H 4.86, N 9.65;
found 74.25, H 4.90, N 9.54.
organization is not in favor of a
p-stacking mode. By lengthening
the conjugated systems with ethylenic bonds in 3, the importance
of the C–FÁ Á ÁpF rises thus favoring parallel arrangement between
the perfluorophenyl cycles, to the detriment of the orthogonal
disposition imposed by FÁ Á ÁF type II interactions, leading to a
3.1.2. 2,5-Bis(pentafluorophenyliminomethyl)thiophene 2
Aldehyde 4 (52 mg, 0.37 mmol) and a catalytic amount of P2O5
were successively added to a solution of perfluoroaniline (200 mg,
1.1 mmol) in ethyl lactate (3 mL) at room temperature. After 8 h
p
-stacking mode.

38
C. Moussallem et al. / Journal of Fluorine Chemistry 178 (2015) 34–39
Fig. 4. X-ray structure of 3. (a) Molecular structure of 3 with anisotropic displacement ellipsoid drawn at 50% probability level. (b) Partial crystal packing of 3 viewed along a
axis C–FÁ Á ÁH–C contacts are presented in orange dotted lines. (c) Stacking mode of molecules along the b axis, shorter intermolecular distances are presented in blue dotted
lines. (For interpretation of the references to color in this figure legend, the reader is referred to the web version of this article.)
stirring, the obtained precipitate was poured in a 10 mL of water-
methanol (50/50 vol) solution. After filtration the solid was
recovered, washed with methanol and dried under vacuum to
give 120 mg of compound 2 (70% yield).
Orange solid, Mp = 216–218 8C.
1H NMR (CDCl3): 8.35 (d, 2H, Himine, J = 8.9 Hz), 7.31 (d, 2H,
Hethylenic, J = 15.6 Hz), 7.24 (s, 2H, Hthiophene), 6.97 (dd, 2H,
Hethylenic, J1 = 15.6 Hz and J2 = 8.9 Hz).
Yellow solid, Mp = 212–214 8C.
13C NMR (CD3COCD3): 166.4, 152.8, 139.1, 122.5, 113.7.
19F NMR (CDCl3): À155.35 (dd, 4F, J = 22 Hz, J = 6 Hz), À162.15
(t, 2F, J = 22 Hz), À165.35 (td, 4F, J = 24 Hz, J = 6 Hz).
MS Maldi-tof: calcd. for C22H8SN2F10 (M + H) 523.0327; found
523.0329.
1H NMR (CDCl3): 8.77 (s, 2H), 7.60 (s, 2H).
13C NMR (CDCl3): 160.0, 146.9, 133.8.
19F NMR (CDCl3): À154.25 (dd, 4F, J = 21 Hz, J = 6 Hz), À162.15
(t, 2F, J = 21 Hz), À165.35 (td, 4F, J = 24 Hz, J = 6 Hz).
MS Maldi-tof: calcd. for C18H4SN2F10 (M + H) 471.0014; found
471.0013.
Elemental analysis for C22H8SN2F10: calcd. C 50.58, H 1.54, N
5.36; found 50.46, H 1.68, N 5.12.
Elemental analysis for C18H4SN2 F10: calcd. C 45.97, H 0.86, N
5.96; found 45.54, H 0.67, N 5.80.
3.2. X-ray structures
3.1.3. 2,5-Bis(pentafluorophenyliminoprop-1-enyl)thiophene 3
A 10 mL tube equipped with a magnetic stirring bar was filled
with 115 mg of dialdehyde 5 (0.6 mmol), 320 mg of perfluoroani-
line (1.7 mmol) in 3 mL of CH2Cl2 and 50 mg of P2O5. The tube was
sealed with a rubber cap and irradiated three times for 10 min at
80 8C and under a pressure of 4.4 bar with a power reactor of
200 W. The mixture was cooled to room temperature, poured on
20 mL of water, extracted twice with CH2Cl2 (2 Â 20 mL) and the
organic phase was dried on MgSO4. After evaporation of the solvent
the residue was purified by a flash chromatography on silica gel in
the presence of several drops of triethylamine (Petroleum ether/
CH2Cl2, 1/1) to give 173 mg (0.33 mmol) of compound 3 (55%
yield).
X-ray single-crystal diffraction data of 1–3 were collected at
293 K for 1 and 2 and at 180 K for 3 on a BRUKER KappaCCD
diffractometer for 1 and 3 and on a STOE IPDS diffractometer for 2,
both equipped with a graphite monochromator using MoK
˚
radiation (l = 0.71073 A). The structures were solved by direct
a
methods and refined by full matrix least squares techniques using
SHELX97 package (G.M. Sheldrick, 1998). All non-H atoms were
refined anisotropically and the H-atoms were found by Fourier
difference for 1 and 2 or were included in the calculation without
refinement for 3. Absorption was corrected by gaussian technique
for 1, multi-scan technique for 2 and SADABS program (Bruker AXS
area detector scaling and absorption correction, v2008/1, Sheldrick,
G.M. (2008)) for 3. Data collection details are found in Table 2.

C. Moussallem et al. / Journal of Fluorine Chemistry 178 (2015) 34–39
39
[3] M.L. Renak, G.P. Bartholomew, S. Wang, P.J. Ricatto, R.J. Lachicotte, G.C. Bazan,
Table 2
J. Am. Chem. Soc. 121 (1999) 7787–7799.
Data collection parameters for the resolved crystal structures of 1–3.
[4] G.P. Bartholomew, X. Bu, G.C. Bazan, Chem. Mater. 12 (2000) 2311–2318.
[5] K. Reichenbacher, H.I. Suss, J. Hulliger, Chem. Soc. Rev. 34 (2005) 22–30.
[6] A. Collas, R. De Borger, T. Amanova, F. Blockhuys, CrystEngComm 13 (2011)
702–710.
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CrystEngComm 6 (2004) 25–28.
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[9] F. Cozzi, S. Bacchi, G. Filippini, T. Pilati, A. Gavezzotti, Chem. Eur. J. 13 (2007)
7177–7184.
Crystal
1
2
3
Formula
C18H14N2S
293
C18H4N2F10
S
C22H8F10N2S
180
Temperature
Molecular
weight
293
290.37
470.29
522.36
Crystal system
Space group
Monoclinic
C2/c
Monoclinic
Cc
Monoclinic
C2/c
˚
[10] T.V. Rybalova, I.Y. Bagryanskaya, J. Struct. Chem. 50 (2009) 741–753.
[11] R. Berger, G. Resnati, P. Metrangolo, E. Weber, J. Hulliger, Chem. Soc. Rev. 40
(2011) 3496–3508.
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(2012) 231–239.
[13] T.S. Thakur, M.T. Kirchner, D. Blaser, R. Boese, G.R. Desiraju, CrystEngComm 12
(2010) 2079–2085.
[14] R. Mariaca, N.-R. Behrnd, P. Eggli, H. Stoeckli-Evans, J. Hulliger, CrystEngComm
8 (2006) 222–232.
[15] S. Bacchi, M. Benaglia, F. Cozzi, F. Demartin, G. Filippini, A. Gavezzotti, Chem.
Eur. J. 12 (2006) 3538–3546.
[16] F. Cozzi, S. Bacchi, G. Filippini, T. Pilati, A. Gavezzotti, CrystEngComm 11
(2009) 1122–1127.
[17] N. Ramasubbu, R. Parthasarathy, P. Murray-Rust, J. Am. Chem. Soc. 108 (1986)
4308–4314.
a (A)
33.668(6)
5.995(1)
7.4708(8)
90
34.915(4)
4.2860(2)
11.5818(8)
90
15.824(4)
6.299(1)
20.023(2)
90
˚
b (A)
˚
c (A)
a
b
g
(8)
(8)
(8)
99.01(2)
90
100.39(1)
90
92.86(1)
90
3
˚
V (A )
1489.3(4)
4
1704.7(7)
4
1993.3(6)
4
Z
Crystal color
Crystal size
(mm3)
Dc (g/cm3)
F (0 0 0)
Yellow pale
0.42 Â 0.10 Â 0.07
Yellow
Orange
0.28 Â 0.13 Â 0.05
0.77 Â 0.77 Â 0.04
1.295
1.832
1.741
608
928
1040
m
(/mm)
0.211
0.304
0.270
[18] M. Fourmigue, Curr. Opin. Solid State Mater. Sci. 13 (2009) 36–45.
[19] A. Priimagi, G. Cavallo, P. Metrangolo, G. Resnati, Acc. Chem. Res. 46 (2013)
2686–2695.
Transmission
(max/min)
0.9862/0.9401
0.9881/0.6486
0.987/0.812
u
(min/max)
4.48/28.07
3.56/25.76
2.04/27.65
[20] F. Meyer, P. Dubois, CrystEngComm 15 (2013) 3058–3071.
(8)
`
`
[21] A.-L. Barres, M. Allain, P. Frere, P. Batail, Isr. J. Chem. 54 (2014) 689–698.
[22] R.B.K. Siram, D.P. Karothu, T.N. Guru Row, S. Patil, Cryst. Growth Des. 13
(2013) 1045–1049.
Data collected
Data unique
R (int)
14,995
1773
6090
3025
0.0461
296
10,385
2265
0.0667
124
0.1331
159
[23] C.-Z. Li, Y. Matsuo, T. Niinomi, Y. Sato, E. Nakamura, Chem. Commun. 46
(2010) 8582–8584.
[24] A. Facchetti, M.H. Yoon, C.L. Stern, H.E. Katz, T.J. Marks, Angew. Chem. Int. Ed.
42 (2003) 3900–3903.
Nb of
parameters
R1 [I > 2s(I)]
0.0457
0.0526
0.0759
wR2 [I > 2
s
(I)]
0.0861
0.1369
0.1318
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R1 [all data]
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0.0737
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