Molecular and Inner Complex Compounds of Dioxomolybdenum(VI) with Disubstituted Salicydenealcoholimines: Crystal Structure of 1 : 1 Dioxo(3,5-Dibromosalicylidenemonoethanoliminato)molybdenum(VI) Solvate with Methanol [MoO2(L1) · MeOH] (L1 = C9H7Br2NO2)

Article abstract of DOI:10.1134/S107032841911006X

Abstract: Complexes of dioxomolybdenum(VI) of the molecular (МоО₂Сl₂ · 2H₂L) and inner complex ([MoO₂L · Solv]) types are synthesized (H₂L are azomethines, derivatives of disubstituted R¹,R²-salicylaldehydes (R¹, R² = 3.5-Вr₂; R¹ = 3-МеО, R² = 5-Вr) and monoethanolamine; Solv is a methanol, dimethylformamide, pyridine, or α-picoline molecule). The cis-octahedral structure of the complexes is concluded on the basis of the IR spectroscopic data. In the molecular compounds, the ligands are coordinated via the O atom of the carbonyl group of the H₂L tautomeric form. In the inner complex compounds, the ligands are coordinated in the deprotonated benzoid form. The structure of [MoO₂(L¹) · МеОН] (I) (where L¹ is C₉H₇Br₂NO₂) is determined by X-ray diffraction analysis (СIF file CCDC no. 1898088). In the mononuclear molecule of compound I, the Mo atom has the octahedral coordination by two oxo ligands, two oxygen atoms, the nitrogen atom of the tridentate bis(chelate) two-charge ligand (L¹)^2–, and the O atom of the methanol molecule. The neutral N(1) and O(1) atoms of the L¹ and МеОН ligands, respectively, are arranged in the trans positions to the O(oxo) ligands. The Mo–N(1) (2.265 ?) and Мо–О(1) (2.372 ?) bonds are substantially elongated due to the structural manifestation of the trans effect of the multiply bonded oxo ligands. The intermolecular hydrogen bonds (МеОН)О–Н···О(oxo) join the molecules into supramolecular 1D chains.

Full text of DOI:10.1134/S107032841911006X

ISSN 1070-3284, Russian Journal of Coordination Chemistry, 2019, Vol. 45, No. 12, pp. 876–882. © Pleiades Publishing, Ltd., 2019.
Russian Text © The Author(s), 2019, published in Koordinatsionnaya Khimiya, 2019, Vol. 45, No. 12, pp. 756–762.
Molecular and Inner Complex Compounds of Dioxomolybdenum(VI)
with Disubstituted Salicydenealcoholimines:
Crystal Structure of 1 : 1 Dioxo(3,5-
Dibromosalicylidenemonoethanoliminato)molybdenum(VI) Solvate
with Methanol [MoO2(L1) · MeOH] (L1 = C9H7Br2NO2)
V. S. Sergienkoa, b, *, V. L. Abramenkoc, Yu. E. Gorbunovaa, and A. V. Churakova
aKurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, 119991 Russia
bAll-Russia Institute of Scientific and Technical Information, Russian Academy of Sciences, Moscow, Russia
cVladimir Dal National University, Lugansk, Ukraine
*е-mail: sergienko@igic.ras.ru
Received February 20, 2019; revised May 27, 2019; accepted June 3, 2019
Abstract—Complexes of dioxomolybdenum(VI) of the molecular (МоО2Сl2 · 2H2L) and inner complex
([MoO2L · Solv]) types are synthesized (H2L are azomethines, derivatives of disubstituted R1,R2-salicylalde-
hydes (R1, R2 = 3.5-Вr2; R1 = 3-МеО, R2 = 5-Вr) and monoethanolamine; Solv is a methanol, dimethylfor-
mamide, pyridine, or α-picoline molecule). The cis-octahedral structure of the complexes is concluded on
the basis of the IR spectroscopic data. In the molecular compounds, the ligands are coordinated via the O
atom of the carbonyl group of the H2L tautomeric form. In the inner complex compounds, the ligands are
coordinated in the deprotonated benzoid form. The structure of [MoO2(L1) · МеОН] (I) (where L1 is
C9H7Br2NO2) is determined by X-ray diffraction analysis (СIF file CCDC no. 1898088). In the mononuclear
molecule of compound I, the Mo atom has the octahedral coordination by two oxo ligands, two oxygen
atoms, the nitrogen atom of the tridentate bis(chelate) two-charge ligand (L1)2–, and the O atom of the meth-
anol molecule. The neutral N(1) and O(1) atoms of the L1 and МеОН ligands, respectively, are arranged in
the trans positions to the O(oxo) ligands. The Mo–N(1) (2.265 Å) and Мо–О(1) (2.372 Å) bonds are sub-
stantially elongated due to the structural manifestation of the trans effect of the multiply bonded oxo ligands.
The intermolecular hydrogen bonds (МеОН)О–Н···О(oxo) join the molecules into supramolecular 1D
chains.
Keywords: synthesis, IR spectroscopy, X-ray diffraction analysis, dioxomolybdenum(VI) complexes, sali-
cylidenealcoholiminate ligands
DOI: 10.1134/S107032841911006X
nemonoethanolamines (R1, R2 = 3.5-Cl2 and R1 =
INTRODUCTION
3-МеО, R2 = H) have the cis-octahedral structure
with the ligands coordinated via the azomethine nitro-
gen atom and two oxygen atoms of the deprotonated
hydroxo groups of the aldehyde and alcohol frag-
ments. The sixth vertex in the octahedron is occupied
by the donor atom of the solvent molecule (Solv is
MeOH).
Salicylidenealcoholimines (Н2L) are potential tri-
dentate dibasic ligands, which react with the d-metal
salts to form inner complex compounds (ICC) of sev-
eral types with the monomeric ([МLn], [М(НL)n],
and di-[МLn]2) or oligomeric ([МLn]m) structures and
exhibit the bi- or tridentate function [1–5]. The
monomeric structures of the complexes МоО2L
(coordination number 5) and МоО2L · Solv (Solv is a
solvent molecule) (coordination number 6) were con-
cluded on the basis of the data of IR and NMR spec-
troscopy [6–9]. Later we found from the X-ray dif-
fraction (XRD) data [1, 2] that the solvated dioxomo-
lybdenum(VI) complexes with substituted salicylide-
O
Solv
R1
O
O
Mo
N
O
CH2
R2
C
H2
876

MOLECULAR AND INNER COMPLEX COMPOUNDS OF DIOXOMOLYBDENUM(VI)
877
For С9Н9Br2NO2 (HL2)
The molecules in the ICC structures are joined in
pairs into centrosymmetrical pseudodimers by nearly
linear intermolecular hydrogen bonds. Similar con-
clusions were made [10, 11] on the basis of the XRD
data for a series of the ICC of dioxomolybdenum(VI)
with monosubstituted salicylidenealcoholimines.
Anal. calcd., %
Found, %
С, 43.81
С, 43.67
Н, 4.41
Н, 4.64
N, 5.11
N, 4.93
IR spectra for HL1 (ν, cm–1): 3310 br, 1652, 1610,
1512, 1350, 1270, 1215, 1158, 1090, 1070, 1030, 908,
870, 770, 748, 630, 580, 495, 447; for HL2 (ν, cm–1):
3400 br, 1650, 1598, 1520, 1412, 1344, 1240, 1210,
1100, 1065, 1040, 1017, 965, 898, 870, 850, 780, 763,
722, 665, 570, 552, 415.
Complexes of the molecular type (adducts) МХn ·
mН2L (Х– is anion) in which the Н2L ligands are coor-
dinated in the neutral form are less known. Continu-
ing the concepts of the structures and properties of the
dioxomolybdenum(VI) complexes with salicylidene-
alcoholimines, we synthesized the molecular com-
pounds (MC) and ICC of dioxomolybdenum(VI) with
disubstituted (R1, R2 = 3,5-Вr2 (Н2L1) and R1 = 3-МеО,
Syntheses of MC МоО2Сl2 · 2H2L1,2 were carried
out by the direct reaction of МоО2Сl2 with salicylide-
neimines similarly to the described procedure [14] in
low-polarity solvents. In diethyl ether the complexes
were formed in an almost quantitative yield. A solution
of the corresponding azomethine (0.002 mol) in ben-
zene was added dropwise with magnetic stirring to
R2 = 5-Вr (Н2L2)) salicylidenemonoethanolimines
and studied them by IR spectroscopy. According to
the elemental analysis data, the synthesized com-
pounds have the compositions МоО2Сl2 · 2Н2L1,2 and
[MoO2L1, 2 · Solv] (Solv is a methanol, DMF, pyri- a solution of molybdenum dioxodichloride (0.199 g,
0.001 mol) in anhydrous diethyl ether (20 mL). The
formed precipitate of the complex was separated on
the Schott filter equipped with the drying system,
washed with ether, and dried in a dry argon flow.
dine, and α-picoline (α-Pіс) molecule).
The structure of the complex [MoO2(L1) · МеОН]
(I) (L1 = C9H7Br2NO2) was determined by the XRD
method.
Syntheses of ICC [MoO2L1,2 · МеОН] were carried
out by the method of ligand exchange between molyb-
denyl acetylacetonate and azomethines [1, 2]. A meth-
anol solution of azomethine (0.001 mol) was added
dropwise to a hot solution of МоО2(Асас)2 (0.326 g,
0.001 mol) in methanol (20 mL), and the reaction
mixture was refluxed for 10–15 min and left to stay at
room temperature for crystallization. The precipitated
crystals of the complexes were filtered off, washed with
cold methanol, and dried first in a dry air flow and
then in a vacuum desiccator over СаСl2. The yields of
the complexes were ~90%. The corresponding solvate
complexes [MoO2L1, 2 · Рy] and [MoO L1, 2 · α-Рic]
EXPERIMENTAL
The initial molybdenum dioxide was synthesized
using the commonly known procedure by the
reduction of molybdenum trioxide (reagent grade)
with hydrogen at 400°С. The reagents and solvents
purchased from Lancaster, Mark, and Fluka were
used.
Synthesis of МоО2Сl2 was carried out by the chlo-
rination of powdered МоО2 at 350°С [12]. The
МоО2Сl2 formed during the reaction was carried away
from the hot zone and condensed in the cold part of
the reactor as pale yellow flakes. An excess chlorine were formed after the recrystallization of the
[MoO2L1, 2 · МеОН] complexes from pyridine or
was removed by purging molybdenum dioxochloride
with dry argon on weak heating (40–50°С) until the
reaction to free chlorine became negative. Since the
pressure of the initial molybdenum dioxide vapors is
very low, the formed МоО2Сl2 needed no additional
purification.
α-picoline. The [MoO2L2 · DMF] complex was
obtained during the synthesis in methanol with the
addition of DMF (2 mL) to the reaction mixture. In all
cases, the yield of the complexes was at least 90%.
The used organic solvents were thoroughly puri-
fied and dehydrated using commonly accepted pro-
cedures [15].
Molybdenyl acetylacetonate МоО2(Aсас)2 was
synthesized using the described procedure [13].
Syntheses of Н2L1 and Н2L2 were carried out by the
condensation of 3,5-dibromo- and 3-methoxy-5-bro-
mosalicylaldehyde and monoethanolamine in boiling
ethanol. After recrystallization from ethanol, they rep-
resented lemon- (HL1) or yellow-colored (HL2) nee-
dles with mp = 147–148 and 124–125°С, respectively.
Elemental analyses of the complexes to the con-
tents of molybdenum and chlorine were conducted
using standard procedures [14]. Analyses of the com-
pounds to the contents of carbon, hydrogen, and
nitrogen were carried out on a Carlo-Erba 1106 Ele-
mental Analyzer CHN analyzer. The electric conduc-
tance of solutions of the complexes was measured on a
conductometer with an alternating current frequency
of 1000 Hz using the bridge scheme in a temperature-
maintained cell with platinized electrodes.
For С9Н9Br2NO2 (HL1)
Anal. calcd., %
Found, %
С, 33.47
С, 33.20
Н, 2.81
Н, 2.98
N, 4.34
N, 4.15
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SERGIENKO et al.
Table 1. Bond lengths (d) and bond angles (ω) in the structure of compound I
Bond
d, Å
Bond
d, Å
Bond
d, Å
Bond
d, Å
Mo(1)–O(4)
Mo(1)–N(1)
O(1)–C(10)
O(1)–H(1)
1.691(5) Mo(1)–O(2)
2.265(5) Mo(1)–O(1)
1.428(9) O(3)–C(9)
0.74(10) O(5)–C(2)
1.723(5)
2.372(5)
1.431(9)
1.338(7)
Mo(1)–O(3)
Br(1)–C(5)
N(1)–C(7)
N(1)–C(8)
1.899(5) Mo(1)–O(5)
1.894(6) Br(2)–C(3)
1.969(4)
1.888(7)
1.440(8)
1.488(11)
1.273(8)
1.465(8) C(8)–C(9)
ω, deg Angle
C(1)–C(7)
Angle
ω, deg
Angle
ω, deg
Angle
ω, deg
O(4)Mo(1)O(2) 107.2(3) O(2)Mo(1)O(5) 99.9(2)
O(4)Mo(1)O(3) 100.0(2) O(3)Mo(1)O(5) 151.6(2)
O(3)Mo(1)N(1) 75.5(2)
O(5)Mo(1)N(1) 79.9(2)
O(4)Mo(1)O(1) 168.5(2)
O(3)Mo(1)O(1) 83.0(2)
O(5)Mo(1)O(1) 77.6(2)
N(1)Mo(1)O(1) 76.4(2)
O(2)Mo(1)O(3)
O(4)Mo(1)O(5)
98.1(2) O(4)Mo(1)N(1) 93.5(2)
95.5(2) O(2)Mo(1)N(1) 159.1(2)
O(2)Mo(1)O(1)
83.2(2)
N(1)C(8)C(9)
O(3)C(9)C(8)
105.5(6)
108.8(5)
C(10)O(1)Mo(1) 130.4(4) C(9)O(3)Mo(1) 120.2(4)
C(7)N(1)Mo(1) 126.9(5)
C(8)N(1)Mo(1) 111.2(4)
C(10)O(1)H(1)
Mo(1)O(1)H(1)
130(9)
99(9)
C(2)O(5)Mo(1) 129.7(4)
C(7)N(1)C(8) 121.8(6)
N(1)C(7)C(1)
124.6(6)
The IR spectra of azomethines and the complexes
were recorded on an IKS-29 spectrometer in a range of
3600–400 cm–1 (suspensions in Nujol).
RESULTS AND DISCUSSION
It is experimentally found that the MC (rather than
ICC) МоО2Сl2 · 2H2L1, 2 were formed by the reaction
of МоО2Сl2 with H2L1, 2 in low-polarity solvents
(diethyl ether, dioxane, and tetrahydrofuran) in spite
of the presence of two hydroxo groups in the sali-
cylidenealcoholimine molecules (Table 2). These
products are amorphous powders undergoing hydro-
X-ray diffraction analysis of complex I was carried
out on an Enraf-Nonius CAD4 automated diffrac-
tometer at room temperature (MoKα radiation, λ =
0.71073 Å, graphite monochromator). The crystals of
complex I (C10H11Br2MoNO5, FW = 480.96) are ort-
horhombic, space group Pbca, a = 6.711(1), b = lysis in air and are easily soluble in methanol to form
13.278(1), c = 31.534(1) Å, V = 2810.0(5) Å3, Z = 8,
calc = 2.274 g/cm3, μ(MoKα) = 6.635 mm–1, F(000) =
conductive solutions. The molar electric conductance
(λМ) of MC solutions in methanol for concentrations
ρ
of 1 × 10–3 mol/L is ~150 cm cm2 mol–1, which char-
acterizes the MC as electrolytes of the 1 : 2 type [14].
1840. The intensities of 12584 reflections (of which
2766 reflections were independent, Rint = 0.0948)
were measured by the ω scan mode in the range 2.58° <
θ < 26.00° (–1 ≤ h ≤ 8, –16 ≤ k ≤ 16, –38 ≤ l ≤ 38). The
structure was solved by a direct method and refined by
full-matrix anisotropic least squares for F2 for all non-
hydrogen atoms (SHELXL-97 [16]). The hydroxyl
hydrogen atom Н(1) was found from the difference
Fourier synthesis and refined isotropically, and other
hydrogen atoms were placed in the calculated posi-
tions and refined by the riding model. The final R fac-
tors were R1 = 0.0460, wR2 = 0.1036 for 1856 reflec-
tions with I > 2σ(I) and 178 refinement parameters,
GООF = 1.010, Δρmax, Δρmin = 1.261, –1.564 e/Å3.
Selected bond lengths and bond angles are given in
Table 1.
Unlike the MC, the slow crystallization of the ICC
[MoOL1,2 · Solv] from organic solvents produces
structured crystals (Table 2). The obtained ICC are
stable in air and poorly soluble in cold polar solvents
(methanol, dimethyl sulfoxide, DMF, pyridine, and
picolines), while they are soluble in them on heating to
form solutions that do not conduct electric current.
The storage of the complexes in air at 140–150°С for 2 h
results in their complete desolvation.
The IR spectra of the obtained ICC (Table 2)
exhibit the low-frequency shift of the stretching vibra-
tion band of the С=N bond by 10–14 cm–1 compared
to its position in the spectra of free ligands, which is
characteristic of inner complex compounds of metals
with azomethine, and the disappearance of the
stretching vibration bands of the hydroxo groups in
a range of 3100–3600 cm–1. The strong band at
1655 cm–1 in the spectrum of [MoO2L2 · DMF] is
attributed to the decreased ν(С=О) frequency of the
The coordinates of atoms and other parameters for
the structure of compound I were deposited with the
Cambridge Crystallographic Data Centre (CIF file
CCDC no. 1898088; deposit@ccdc.cam.ac.uk or
http://www.ccdc.cam.ac.uk/data_request/cif).
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SERGIENKO et al.
Br(2)
C(10)
O(1)
C(3)
O(2)
O(3)
O(5)
C(4)
C(2)
C(5)
Mo(1)
C(1)
C(6)
Br(1)
O(4)
N(1)
C(7)
С(9)
С(8)
Fig. 1. Structure of the molecule of compound I. Thermal ellipsoids are given with 50% probability.
coordinated DMF molecule. The shift of a series of and dioxo cations of VIВ Group with two multiply
bands to a range of ~1000–1610 cm–1 corresponding
to the vibrations of the bonds of the heterocycle is
observed in the spectra of [MoO2L1, 2 · Solv], where
Solv is pyridine or α-picoline [17].
bonded oxo ligands in the cis position. In the MC, the
vertices of the octahedron contain the terminal oxygen
atoms, two carbonyl O atoms of the quinoid tautom-
eric form of oxoazomethines in the trans positions to
the oxo ligands according to the principle of self-con-
sistency [25], and two chlorine atoms in the trans posi-
tions to each other. The vertices of the octahedron in
the ICC are occupied by two multiply bonded O
atoms: the donor N atom of the azomethine group
(trans to the oxo ligands) and two O atoms of the
deprotonated hydroxo groups of the aldehyde and
alcohol fragments in the cis positions to the oxo
ligands. The sixth coordination site (trans to the oxo
ligand) is occupied by the donor atoms of the coordi-
nated solvent molecules.
The 1600–1700 cm–1 range of the spectra of the
MC contains the intense band at ~1660 cm–1, which
should be ascribed (with the highest probability) to the
stretching vibration band of the С=О quinoid
(ketoamine) tautomer increased due to complex for-
mation. The stabilization of the quinoid tautomeric
form of o-oxyazomethines during the formation of
complexes of the molecular type was repeatedly dis-
cussed [18–20]. Scarce literature data on the XRD of
the molecular complexes of a series of metals with
o-oxyazomethines [21–24] also confirm the coordi-
nation of the ligands in the quinoid tautomeric form.
The strong bands at 890–930 cm–1 are attributed to
the symmetric and antisymmetric stretching vibra-
tions of the Мо=О bond of the cis-МоО2 group [1, 2].
New absorption bands appear in the IR spectra of the
complexes at low frequencies: at 540–580 cm–1 (in the
spectra of the MC) and at 520–540 and 470–475 cm–1
(in the spectra of the ICC), which should be assigned
to the stretching vibrations of the Мо–ОHL or Мо–NL
and Мо–ОL bonds, respectively [1, 2, 14].
The structure of ICC I was determined by the XRD
method. In the mononuclear molecule of complex I
(Fig. 1), the molybdenum atom has the octahedral
coordination mode by two oxo ligands О(2) and О(4),
two oxygen atoms О(3) and О(5) and the N(1) nitro-
gen atom of the tridentate bis(chelate) two-charge
ligand (L1)2–, and the O(1) atom of the methanol mol-
ecule. According to the principle of self-consistency
[25], the neutral N(1) and O(1) atoms of the L1 and
МеОН ligands, respectively, are arranged in the
trans positions to the O(oxo) ligands. The Mo–N(1)
Based on the obtained experimental results and (2.265 Å) and Мо–О(1) (2.372 Å) bonds are substan-
taking into account literature data, we may conclude tially elongated due to the structural manifestation of
that the studied MC and ICC of dioxomolybde- the trans effect of the multiply bonded oxo ligands.
num(VI) with substituted salicylidenemonoethano- These bonds are also appreciably longer than the stan-
limines have the octahedral structure typical of oxo dard distances Мо–О(ST) (2.04 Å) and Мо–N(ST)
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The molecules of compound I are joined in pairs by
the hydrogen bond О(1)–Н(1)…О(2) (0.5 + х, у, 0.5 – z)
between the methanol molecule and one of the oxo
ligands (О(1)–Н(1) 0.74(10), Н(1)…О(2) 2.07(10),
О(1)…О(2) 2.695(6) Å, angle О(1)Н(1)О(2)
143(13)°). The 1D chains along the с axis of the crystal
are formed due to these hydrogen bonds (Fig. 2). Evi-
dently, the participation of the oxo ligand О(2) in the
hydrogen bond is a reason for the Мо–О(2) bond to be
somewhat longer (1.723 Å) than Мо–О(4) (1.691 Å).
ACKNOWLEDGMENTS
The X-ray diffraction analysis was carried out at the
Center for Collective Use of Physical Methods of Investiga-
tion at the Kurnakov Institute of General and Inorganic
Chemistry (Russian Academy of Sciences).
b
0
FUNDING
a
This work was carried out in the framework of the state
task of the Kurnakov Institute of General and Inorganic
Chemistry (Russian Academy of Sciences) in the area of
basic research.
Fig. 2. Chains joined by hydrogen bonds in the structure of
compound I.
(2.10 Å) [25]. The Мо–О(oxo) bonds (average 1.707
0.016 Å) are typical in length and correspond to the
increased multiplicity. Fairly short Мо–О(3)cis and
CONFLICT OF INTEREST
The authors declare that they have no conflicts of interest.
Мо–О(5)(L1)cis bonds differ substantially in length
(1.899 and 1.969 Å, respectively). The Mo atom is
shifted from the center of the МоО5N octahedron to
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Translated by E. Yablonskaya
https://doi.org/10.1134/S0036023617120019
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Vol. 45
No. 12
2019