Bromide complexes of bismuth with 4-bromobenzyl-substituted cations of pyridinium family

Article abstract of DOI:10.1016/j.molstruc.2019.126955

Two bromobismuthate (III) complexes containing 4-bromobenzyl-substituted pyridinium cations – (1-(4-BrBz)Py)₃[Bi₂Br₉] (1) and (1-(4-BrBz)-2-MePy)₃[BiBr₆] (2) – were prepared by reactions of Bi₂

Full text of DOI:10.1016/j.molstruc.2019.126955

Journal of Molecular Structure 1199 (2020) 126955
Contents lists available at ScienceDirect
Journal of Molecular Structure
journal homepage: http://www.elsevier.com/locate/molstruc
Bromide complexes of bismuth with 4-bromobenzyl-substituted
cations of pyridinium family
,
, c, d,
Igor D. Gorokh a b, Sergey A. Adonin a
*, Andrey N. Usoltsev a, Alexander S. Novikov e,
Denis G. Samsonenko a f, Sergey V. Zakharov g, Maxim N. Sokolov a
,
,
, f, h
Vladimir P. Fedin a
,
f
a Nikolaev Institute of Inorganic Chemistry SB RAS, 630090, 3 Lavrentiev Av., Novosibirsk, Russia
b Skolkovo Institute of Science and Technology, Center for Electrochemical Energy Storage, 143026, Nobel St. 3, Moscow, Russia
c Tobolsk Industrial Institute (Branch of Tyumen Industrial University), 626158, Zona Vuzov 5, Tobolsk, Russia
d South Ural State University, Chessslyabinsk, 454080, Russia
e Saint Petersburg State University, Institute of Chemistry, 199034, Universitetskaya Nab. 7-9, Saint Petersburg, Russia
f Novosibirsk State University, 630090, Pirogova St. 2, Novosibirsk, Russia
g Irkutsk National Research Technical University, 664074, Lermontov St. 83, Irkutsk, Russia
h Kazan Federal University, Alexander Butlerov Institute of Chemistry, Lobachevskogo St. 1/29, 420008, Kazan, Russia
a r t i c l e i n f o
a b s t r a c t
Article history:
Two bromobismuthate (III) complexes containing 4-bromobenzyl-substituted pyridinium cations e (1-
(4-BrBz)Py)3[Bi2Br9] (1) and (1-(4-BrBz)-2-MePy)3[BiBr6] (2) e were prepared by reactions of Bi2O3 and
corresponding pyridinium bromides in HBr. In the structure of 1 there are weak contacts between the Br
atoms of 1-(4-BrBz)Pyþ and bromide ligands of [Bi2Br9]3-, while in the case of 2 such interactions are
absent. The contributions of halogen and hydrogen bonding were estimated by Hirshfeld surface analysis
(HSA); additionally, energies of Br/Br type I halogen-halogen contacts were calculated.
© 2019 Elsevier B.V. All rights reserved.
Received 9 April 2019
Received in revised form
19 August 2019
Accepted 19 August 2019
Available online 20 August 2019
Keywords:
Halide complexes
Hirshfeld surface analysis
Bismuth
Supramolecular contacts
1. Introduction
with certain molecular structure remains a challenging task (and it
is unclear whether such synthetic approaches can be found),
Anionic halide complexes of p-block elements have moved close
to the center stage of current coordination chemistry. The activity
in this field is stimulated by peculiar physical properties of the
compounds in this class, such as photocatalytic activity (especially
for Cu and Ag complexes) [1e3], unusual solvent-induced color
changes [4], luminescence [5e7], ferroelectric behaviour [8e14]
etc. One of the most prominent topics is the use of halide (first of all,
iodide) complexes as light absorbers in solar cells [15e20]. For this
area, there are several crucial parameters which must be achieved;
those are: 1) thermal and photostability, 2) lower optical band gap
and 3) preferably structure of higher dimensionality in order to
achieve isotropy. Since controllable preparation of halometalates
screening remains the key method for the search of compounds
with desired properties. Recently we reported [21] that hal-
obismuthate (III) complexes with halogen-substituted cations of
pyridinium family can demonstrate unusual optical behaviour due
to formation of halogen-halogen short contacts in solid state. In
order to check whether such effects are expandable on the com-
plexes with other aromatic cations able to form halogen-halogen
short contacts in solid state, we used 4-bromobenzyl-substituted
Py derivatives. We consider both type I interactions which assumed
to appear due to crystal packing effects and type II interactions
(“classic” halogen bonding (XB)). In this work we report two new
bromobismuthates (III) e (1-(4-BrBz)Py)3[Bi2Br9] (1) and (1-(4-
BrBz)-2-MePy)3[BiBr6] (2) and discuss the features of supramolec-
ular contacts in their structures.
* Corresponding author. Nikolaev Institute of Inorganic Chemistry SB RAS,
630090, 3 Lavrentiev av., Novosibirsk, Russia.
E-mail address: adonin@niic.nsc.ru (S.A. Adonin).
https://doi.org/10.1016/j.molstruc.2019.126955
0022-2860/© 2019 Elsevier B.V. All rights reserved.

2
I.D. Gorokh et al. / Journal of Molecular Structure 1199 (2020) 126955
Fig. 1. Structures of 1-(4-BrBz)Pyþ (left) and 1-(4-BrBz)-2-MePyþ (right) cations.
2. Experimental part
Fig. 2. Crystal packing in the structure of 1.
All experiments were carried out in air. 1-(4-bromobenzyl)pyr-
idinium and 1-(4-bromobenzyl)-2-methylpyridinium (Fig. 1) bro-
mides were prepared by reactions of pyridine or 2-picoline with 4-
bromobenzyl bromide (1:1.1) in acetonitrile (24 h, r.t., yields are
close to quantitative). Elemental analysis was performed on a Euro
NA 3000 Elemental Analyzer (EuroVector).
Synthesis of (1-(4-BrBz)Py)3[Bi2Br9] (1). 43 mg (0.099 mmol) of
Bi2O3 were dissolved in 15 ml 2 M HBr; then solution of 1-(4-BrBz)
PyBr (90 mg, 0.276 mmol) in 15 ml of 2 M HBr was added. Within 1
day, there form pale yellow crystals of 1. Yield 79%. For
HBr was added. Within 1 day, there form pale yellow crystals of 2.
Yield 81%. For C39H39N3BiBr9 calcd, %: C, 31.9; H, 2.7; N, 2.9; found,
%: C, 31.8; H, 2.7; N, 2.8.
X-ray Diffractometry. Diffraction data for single crystals 1 and 2
were obtained at 130 K on an automated Agilent Xcalibur diffrac-
tometer equipped with an area AtlasS2 detector (graphite mono-
chromator,
l
(MoK
a
) ¼ 0.71073 Å,
u-scans). Integration, absorption
correction, and determination of unit cell parameters were per-
formed using the CrysAlisPro program package (CrysAlisPro
1.171.38.41. Rigaku Oxford Diffraction: The Woodlands, TX, USA,
2015). The structures were solved by dual space algorithm
(SHELXT) [22] and refined by the full-matrix least squares tech-
nique (SHELXL) [23] in the anisotropic approximation (except
C
36H33N3Bi2Br12 calcd, %: C, 23.1; H, 1.8; N, 2.2; found, %: C, 23.0; H,
1.8; N, 2.2.
Synthesis
of
(1-(4-BrBz)-2-MePy)3[BiBr6]
(2).
15 mg
(0.032 mmol) of Bi2O3 were dissolved in 10 ml of 2 M HBr; then
solution of 1-(4-BrBz)-2-MePyBr (16 mg, 0.048 mmol) in 8 ml of
Table 1
Crystal data and structure refinement for 1 and 2.
Compound
1
2
Empirical formula
M, g/mol
Crystal system
Space group
a, Å
C36H33Bi2Br12N3
1884.53
Orthorhombic
Pca21
27.3642(13)
12.6778(5)
27.5745(13)
90
90
90
9566.1(7)
8
2.617
C39H39BiBr9N3
1477.90
Monoclinic
P21/n
15.4597(5)
17.1922(4)
18.5102(6)
90
113.447(4)
90
4513.5(3)
4
b, Å
c, Å
a
b
g
, deg.
, deg.
, deg.
V, Å3
Z
D(calcd), g/cm3
2.175
11.905
m
, mmꢀ1
17.403
F(000)
6848
2768
Crystal size, mm
0.24 ꢁ 0.17 ꢁ 0.05
0.39 ꢁ 0.33 ꢁ 0.28
q
range for data collection, deg.
3.36e25.35
3.30e28.97
Index ranges
Reflections collected/independent
Rint
ꢀ20 ꢂ h ꢂ 32, ꢀ15 ꢂ k ꢂ 10, ꢀ33 ꢂ l ꢂ 25
ꢀ15 ꢂ h ꢂ 21, ꢀ22 ꢂ k ꢂ 23, ꢀ23 ꢂ l ꢂ 19
24993/13443
0.0449
37580/10442
0.0286
Reflections with I > 2
s(I)
12243
8877
Goodness-of-fit on F [2]
1.031
1.036
Final R indices [I > 2
R indices (all data)
s
(I)]
R1 ¼ 0.0415, wR2 ¼ 0.0930
R1 ¼ 0.0486, wR2 ¼ 0.0963
1.398/ꢀ1.138
R1 ¼ 0.0247, wR2 ¼ 0.0460
R1 ¼ 0.0351, wR2 ¼ 0.0480
1.249/ꢀ1.131
Largest diff. peak/hole, e/Å3

I.D. Gorokh et al. / Journal of Molecular Structure 1199 (2020) 126955
3
The Cambridge Crystallographic Data Center at http://www.ccdc.
cam.ac.uk/data_request/cif.
3. Results and discussion
According to the Cambridge Structural Database (CSD), there are
over ten crystal structures containing 1-(4-bromobenzyl)pyr-
idinium cation [24e27]. One of those (CCDC 811817) contains
[CuBr4]2- as a counter anion. Our scrutiny did not detect Br/Br
interactions classifiable as halogen-halogen short contacts. In all
cases these distances exceed 3.66 Å, which is the sum of Bondi's van
der Waals radii for two Br atoms [28,29]. Structures with 1-(4-
bromobenzyl)-2-methylpyridinium have not been reported.
In the structure of 1, the anionic part consists of well-known
[11,12,30e37] binuclear [Bi2Br9]3- units. The BieBr bond lengths
are within the usual range (Bi e Brterm ¼ 2.675e2.803 Å; Bi e m2
-
Br ¼ 2.947e3.162 Å, respectively). The search for possible Br/Br
contacts revealed that relevant distances are only slightly under the
sum of van der Waals radii (3.648 Å in 1 vs 3.66 Å for two Br van der
Waals radii), indicating weak interactions between the Br atoms of
4-bromobenzyl units and terminal Br ligands. The shortest H/Br
contacts in 1 are 2.765 Å, and these involve m2-Br and CH2 fragment
of cation, while the contacts with Brterm are longer; similar effects
were found in other structures of [Bi2Br9]3- salts [38]. The crystal
packing in 1 is shown in Fig. 2 (additional figures illustrating H/Br
and Br/Br contacts are given in SI). The bromobismuthate units in
2 are mononuclear [BiBr6]3- (Fig. 3) with slightly distorted octa-
hedral geometry at Bi (BieBr ¼ 2.786e2.923 Å). The shortest H/Br
Fig. 3. Crystal packing in the structure of 2.
hydrogen atoms). Positions of hydrogen atoms of organic ligands
were calculated geometrically and refined in the riding model.
Residual density on Bi and Br does not exceed the limits common
for heavier atoms. The crystallographic data and details of the
structure refinements are summarized in Table 1. CCDC
1908927e1908928 contain the supplementary crystallographic
data for this paper. These data can be obtained free of charge from
Table 2
Results of the HSA for the X-ray structures of 1 and 2.
X-ray structure
Contributions of different intermolecular contacts to the molecular Hirshfeld surfacea
1
Anionic part: BreH 90.5%, BreC 5.0%, BreBr 4.1%
Cationic part: BreH 44.9%, HeH 18.3%, CeH 16.9%, BreC 12.9%, CeC 3.8%, BreBr 1.4%, NeC 1.3%
2
Anionic part: BreH 91.7%, BreC 6.0%, BreN 1.6%
Cationic part: HeH 38.5%, BreH 31.9%, CeH 17.0%, BreC 6.0%, CeC 4.8%, NeH 1.2%
a
The contributions of all other intermolecular contacts do not exceed 1%.
Fig. 4. Hirshfeld surfaces for 1 (left) and 2 (right) (anionic and cationic parts).

4
I.D. Gorokh et al. / Journal of Molecular Structure 1199 (2020) 126955
Table 3
Values of the density of all electrons (r(r)), Laplacian of electron density (V [2]r(r)) and appropriate l2 eigenvalue, energy density (Hb), potential energy density (V(r)), and
Lagrangian kinetic energy (G(r)) (a.u.) at the bond critical point (3, ꢀ1), corresponding to non-covalent interactions Br/Br (type I halogen-halogen short contacts) in su-
pramolecular structure of 1, bond length (l) (Å), Wiberg bond index (WI), as well as energy for this contact Eint (kcal/mol), defined by different approaches.
a
b
c
d
r
(r)
V [2]
0.018
r
(r)
l2
Hb
V(r)
G(r)
Eint
1.3
Eint
1.1
Eint
1.5
Eint
1.4
le
WI
0.007
ꢀ0.008
0.000
ꢀ0.004
0.004
3.647
0.01
a
Eint ¼ eV(r)/253
.
b
Eint ¼ 0.429G(r) [54].
c
d
e
Eint ¼ 0.58(ꢀV(r)) (correlation developed exclusively for non-covalent interactions involving bromine atoms) [55].
Eint ¼ 0.57G(r) (correlation developed exclusively for non-covalent interactions involving bromine atoms) [54].
The shortest van der Waals radius for Br atom is 1.83 Å29
.
contacts are 2.710 Å (with H atoms of phenyl rings), and the Br/Br
distances exceed the sum of corresponding van der Waals radii,
indicating lack of such interactions. Both complexes were isolated
as pure phases, according to the PXRD data (see SI).
contacts [41,42]) takes place as well.
For estimation of the energies of these type I halogen-halogen
short contacts which, in our opinion, are related to the phenome-
non of halogen bonding [41,42], we performed DFTcalculations and
topological analysis of the electron density distribution (QTAIM
theory) [43] for 1. Previously, this approach was successfully uti-
lized for the studies of various non-covalent interactions in coor-
dination compounds [44e51]. Results are summarized in Table 3,
For estimation of relative contributions of different contacts to
the crystal packing, we performed Hirshfeld surface analysis (HSA)
for 1 and 2, see Table 2 and SI for details. For the visualization, we
have used a mapping of the normalized contact distance (dnorm); its
negative value enables identification of molecular regions of sub-
stantial importance for detection of short contacts. Fig. 4 depicts
the Hirshfeld surfaces for 1 and 2 (anionic and cationic parts). In
these Hirshfeld surfaces, the regions of shortest intermolecular
contacts visualized by red circle areas. In both cases, the domi-
nating contacts are Br/H and/or H/H (this situation is common
for halometalates [39,40]); however, in the case of 1, contribution of
abovementioned Br/Br interactions (type I halogen-halogen short
the contour line diagram of the Laplacian distribution V [2]r(r),
bond paths, and selected zero-flux surfaces as well as reduced
density gradient (RDG) isosurface [52] for non-covalent in-
teractions Br/Br in supramolecular structure of 1 are shown in
Fig. 5.
The Laplacian of electron density is typically decomposed into
the sum of contributions along the three principal axes of maximal
variation, giving the three eigen values (l1, l2 and l3) of the Hessian
matrix. In line with common practice, the sign of l2 can be utilized
to distinguish bonding (attractive, l2 < 0) weak interactions from
non-bonding ones (repulsive, l2 > 0). Thus, the discussed above
non-covalent interactions Br/Br (type I halogen-halogen short
contacts) in supramolecular structure of 1 are attractive (Table 3).
The QTAIM analysis demonstrates the presence of appropriate
bond critical point (3, ꢀ1) (BCP) for non-covalent interactions
Br/Br in supramolecular structure of 1 (Table 3). The low magni-
tude of the electron density, positive value of the Laplacian, and
very low energy density in this BCP are typical for non-covalent
interactions involving halogen atoms [56,57]. We have defined
energy for this weak contact Br/Br according to several proced-
ures [53e55]; depending on the approach used, the strength of this
contact vary in the ranges 1.1e1.5 kcal/mol. The balance between
the Lagrangian kinetic energy G(r) and potential energy density
V(r) at the BCP reveals that a covalent contribution is absent in
Br/Br supramolecular contacts in 1 [58], which correlates well
with negligible Wiberg bond indices for these interactions. The
NBO charges on the bromine atoms involving in non-covalent in-
teractions Br/Br in supramolecular structure of 1 are ꢀ0.44
(anionic part) and 0.12 (cationic part).
Overall, analysis of both geometries and energies of Br/Br in-
teractions reveals that those should be rather classified as Type I
halogen$$$halogen short contacts according to the classification by
Metrangolo et al.
According to the TGA data (see SI), both 1 and 2 reveal high
thermal stability (decomposition begins at z 200 ꢃC for
1
and z220 ꢃC for 2). These observations agree well with the in-
vestigations of thermal stability of bromobismuthates(III) made by
us earlier [59].
Fig. 5. Contour line diagram of the Laplacian distribution V [2]
selected zero-flux surfaces (top) and RDG isosurface (bottom) referring to non-
covalent interactions Br/Br in (packing induced contact aka type halogen-
halogen short contact). Bond critical points (3, ꢀ1) are shown in blue, nuclear crit-
ical points (3, ꢀ3) e in pale brown, length units e Å, isovalues on contour lines and
RDG isosurface values on the color scheme are given in a.u.
r(r), bond paths and
4. Conclusions
1
I
With 4-bromobenzyl-substituted pyridinium salts as pre-
cursors, we prepared two new bromobismuthate complexes.
Combination of Hirshfeld Surface Analysis (HSA) and DFT show that

I.D. Gorokh et al. / Journal of Molecular Structure 1199 (2020) 126955
5
1281e1284.
the desired Br/Br contacts indeed appear in the solid state, but
their role in crystal packing is minor and their energies are low.
From the point of view of halometalate crystal engineering,
halogen-substituted pyridiniums [21,60] still remain better candi-
date for XB formation because of higher charge anisotropy of bro-
mide atom bounded to electron deficientpyridinium moiety.
[24] X.M. Ren, H. Okudera, R.K. Kremer, Y. Song, C. He, Q.J. Meng, P.H. Wu, Inorg.
Chem. 43 (2004) 2569e2576.
[25] X. Ren, Q. Meng, Y. Song, C. Lu, C. Hu, X. Chen, Inorg. Chem. 41 (2002)
5686e5692.
[26] X. Ren, J. Ma, C. Lu, S. Yang, Q. Meng, P. Wu, Dalton Trans. (2003) 1345e1351.
[27] C. Ni, D. Dang, Z. Ni, Y. Li, J. Xie, Q. Meng, Y. Yao, J. Coord. Chem. 57 (2004)
1529e1536.
[28] M. Mantina, A.C. Chamberlin, R. Valero, C.J. Cramer, D.G. Truhlar, J. Phys.
Chem. A 113 (2009) 5806e5812.
Acknowledgements
[29] A. Bondi, J. Phys. Chem. 70 (1966) 3006e3007.
ꢀ
[30] M. Wojtas, R. Jakubas, Z. Ciunik, W. Medycki, J. Solid State Chem. 177 (2004)
This work was supported by Russian Science Foundation (Grant
No. 18-73-10040).
1575e1584.
[31] I.A. Ahmed, R. Blachnik, G. Kastner, W. Brockner, Z. Anorg. Allg. Chem. 627
(2001) 2261.
ꢀ
[32] B. Ptaszynski, Thermochim. Acta 197 (1992) 479e490.
Appendix A. Supplementary data
[33] G.A. Bowmaker, P.C. Junk, A.M. Lee, B.W. Skelton, A.H. White, Aust. J. Chem. 51
(1998) 293.
[34] Y.-H. Peng, S.-F. Sun, X.-H. Yang, T. Gao, Y. Li, J. Wang, J. Mol. Struct.
1056e1057 (2014) 202e208.
[35] V.V. Sharutin, I.V. Yegorova, N.N. Klepikov, E.A. Boyarkina, O.K. Sharutina,
Russ. J. Inorg. Chem. 54 (2009) 52e68.
Supplementary data to this article can be found online at
https://doi.org/10.1016/j.molstruc.2019.126955.
[36] W.-X. Chai, J. Lin, L. Song, L.-S. Qin, H.-S. Shi, J.-Y. Guo, K.-Y. Shu, Solid State Sci.
14 (2012) 1226e1232.
References
[37] G.A. Bowmaker, J.M. Harrowfield, P.C. Junk, B.W. Skelton, A.H. White, Aust. J.
Chem. 51 (1998) 285.
[1] X.-W. Lei, C.-Y. Yue, F. Wu, X.-Y. Jiang, L.-N. Chen, Inorg. Chem. Commun. 77
(2017) 64e67.
[2] X.-W. Lei, C.-Y. Yue, J.-C. Wei, R.-Q. Li, F.-Q. Mi, Y. Li, L. Gao, Q.-X. Liu, Chem.
Eur J. 23 (2017) 14547e14553.
[3] K.-B. Chu, J.-L. Xie, W.-J. Chen, W.-X. Lu, J.-L. Song, C. Zhang, Polyhedron 151
(2018) 146e151.
[4] B. Wagner, N. Dehnhardt, M. Schmid, B.P. Klein, L. Ruppenthal, P. Müller,
M. Zugermeier, J.M. Gottfried, S. Lippert, M.-U. Halbich, A. Rahimi-Iman,
J. Heine, J. Phys. Chem. C 120 (2016) 28363e28373.
[5] J.C. Ahern, A.D. Nicholas, A.W. Kelly, B. Chan, R.D. Pike, H.H. Patterson, Inorg.
Chim. Acta 478 (2018) 71e76.
[6] A.W. Kelly, A. Nicholas, J.C. Ahern, B. Chan, H.H. Patterson, R.D. Pike, J. Alloy.
Comp. 670 (2016) 337e345.
[7] J.R. Sorg, T. Wehner, P.R. Matthes, R. Sure, S. Grimme, J. Heine, K. Müller-
Buschbaum, Dalton Trans. 47 (2018) 7669e7681.
[38] S.A. Adonin, I.D. Gorokh, D.G. Samsonenko, O.V. Antonova, I.V. Korolkov,
M.N. Sokolov, V.P. Fedin, Inorg. Chim. Acta 469 (2018), 32-27.
[39] O. Ben Moussa, H. Chebbi, M.F. Zid, J. Mol. Struct. 1180 (2019) 72e80.
[40] Z. Ouerghi, T. Roisnel, R. Fezai, R. Kefi, J. Mol. Struct. 1173 (2018) 439e447.
[41] G. Cavallo, P. Metrangolo, T. Pilati, G. Resnati, M. Sansotera, G. Terraneo, Chem.
Soc. Rev. 39 (2010) 3772.
[42] G. Cavallo, P. Metrangolo, R. Milani, T. Pilati, A. Priimagi, G. Resnati,
G. Terraneo, Chem. Rev. 116 (2016) 2478e2601.
[43] R.F.W. Bader, Chem. Rev. 91 (1991) 893e928.
[44] X. Ding, M.J. Tuikka, P. Hirva, V.Y. Kukushkin, A.S. Novikov, M. Haukka,
CrystEngComm 18 (2016) 1987e1995.
[45] A.S. Novikov, Inorg. Chim. Acta 471 (2018) 126e129.
[46] D.M. Ivanov, A.S. Novikov, I.V. Ananyev, Y.V. Kirina, V.Y. Kukushkin, Chem.
Commun. 52 (2016) 5565e5568.
[47] D.M. Ivanov, M.A. Kinzhalov, A.S. Novikov, I.V. Ananyev, A.A. Romanova,
V.P. Boyarskiy, M. Haukka, V.Y. Kukushkin, Cryst. Growth Des. 17 (2017)
1353e1362.
[48] L.E. Zelenkov, D.M. Ivanov, M.S. Avdontceva, A.S. Novikov, N.A. Bokach,
Z. Krist. - Cryst. Mater. 234 (2019) 9e17.
[8] M. We˛cławik, A. Ga˛gor, R. Jakubas, A. Piecha-Bisiorek, W. Medycki, J. Baran,
ꢀ
P. Zielinski, M. Gała˛zka, Inorg. Chem. Front. 3 (2016) 1306e1316.
[9] A. Piecha-Bisiorek, R. Jakubas, W. Medycki, M. Florek-Wojciechowska,
M. Wojciechowski, D. Kruk, J. Phys. Chem. A 118 (2014) 3564e3571.
ꢀ
ꢀ
[10] M. Chanski, A. Białonska, R. Jakubas, A. Piecha-Bisiorek, Polyhedron 71 (2014)
69e74.
[49] E.V. Andrusenko, A.S. Novikov, G.L. Starova, N.A. Bokach, Inorg. Chim. Acta 447
(2016) 142e149.
[50] M. Bulatova, A.A. Melekhova, A.S. Novikov, D.M. Ivanov, N.A. Bokach, Z. Krist. -
Cryst. Mater. 233 (2018) 371e377.
ꢀ
[11] P. Szklarz, R. Jakubas, A. Piecha-Bisiorek, G. Bator, M. Chanski, W. Medycki,
J. Wuttke, Polyhedron 139 (2018) 249e256.
ꢀ
[12] M. Wojtas, R. Jakubas, J. Baran, Vib. Spectrosc. 39 (2005) 23e30.
[13] B. Kulicka, R. Jakubas, A. Pietraszko, G. Bator, J. Baran, Solid State Sci. 6 (2004)
1273e1286.
[14] A. Piecha, R. Jakubas, V. Kinzhybalo, T. Lis, J. Mol. Struct. 887 (2008) 194e200.
[15] L.A. Frolova, D.V. Anokhin, A.A. Piryazev, S.Y. Luchkin, N.N. Dremova,
P.A. Troshin, J. Phys. Chem. Lett. 8 (2017) 1651e1656.
[16] L.A. Frolova, D.V. Anokhin, A.A. Piryazev, S.Y. Luchkin, N.N. Dremova,
K.J. Stevenson, P.A. Troshin, J. Phys. Chem. Lett. 8 (2017) 67e72.
[17] L.A. Frolova, N.N. Dremova, P.A. Troshin, Chem. Commun. 51 (2015)
14917e14920.
[18] A.M. Ganose, C.N. Savory, D.O. Scanlon, Chem. Commun. 53 (2017) 20e44.
[19] T.A. Shestimerova, N.A. Yelavik, A.V. Mironov, A.N. Kuznetsov, M.A. Bykov,
A.V. Grigorieva, V.V. Utochnikova, L.S. Lepnev, A.V. Shevelkov, Inorg. Chem. 57
(2018) 4077e4087.
[20] T.A. Shestimerova, N.A. Golubev, N.A. Yelavik, M.A. Bykov, A.V. Grigorieva,
Z. Wei, E.V. Dikarev, A.V. Shevelkov, Cryst. Growth Des. 18 (2018) 2572e2578.
[21] S.A. Adonin, I.D. Gorokh, A.S. Novikov, D.G. Samsonenko, I.V. Yushina,
M.N. Sokolov, V.P. Fedin, CrystEngComm 20 (2018) 7766e7772.
[22] G.M. Sheldrick, Acta Crystallogr. Sect. C Struct. Chem. 71 (2015) 3e8.
[23] C.B. Hübschle, G.M. Sheldrick, B. Dittrich, J. Appl. Crystallogr. 44 (2011)
[51] Z.M. Bikbaeva, D.M. Ivanov, A.S. Novikov, I.V. Ananyev, N.A. Bokach,
V.Y. Kukushkin, Inorg. Chem. 56 (2017) 13562e13578.
ꢀ
[52] E.R. Johnson, S. Keinan, P. Mori-Sanchez, J. Contreras-García, A.J. Cohen,
W. Yang, J. Am. Chem. Soc. 132 (2010) 6498e6506.
[53] E. Espinosa, E. Molins, C. Lecomte, Chem. Phys. Lett. 285 (1998) 170e173.
[54] M.V. Vener, A.N. Egorova, A.V. Churakov, V.G. Tsirelson, J. Comput. Chem. 33
(2012) 2303e2309.
[55] E. V Bartashevich, V.G. Tsirelson, Russ. Chem. Rev. 83 (2014) 1181e1203.
[56] A.S. Novikov, D.M. Ivanov, Z.M. Bikbaeva, N.A. Bokach, V.Y. Kukushkin, Cryst.
Growth Des. 18 (2018) 7641e7654.
[57] S.V. Baykov, U. Dabranskaya, D.M. Ivanov, A.S. Novikov, V.P. Boyarskiy, Cryst.
Growth Des. 18 (2018) 5973e5980.
[58] E. Espinosa, I. Alkorta, J. Elguero, E. Molins, J. Chem. Phys. 117 (2002)
5529e5542.
[59] S.A. Adonin, I.D. Gorokh, D.G. Samsonenko, A.S. Novikov, I.V. Korolkov,
P.E. Plyusnin, M.N. Sokolov, V.P. Fedin, Polyhedron 159 (2019) 318e322.
ꢀ
[60] V. Gomez, O. Fuhr, M. Ruben, CrystEngComm 18 (2016) 8207e8219.