Crystal structure of bis­[(η5-tert-butyl­cyclo­pentadien­yl)tri­carbonyl­molybdenum(I)](Mo—Mo)

Ibrahimova, N.Z.; Tagiyev, D.B.; Lyatifov, I.U.; Akkurt, M.; Hasanov, K.I.; Bhattarai, A.

doi:10.1107/S2056989024006959

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ISSN: 2056-9890

Volume 80| Part 8| August 2024| Pages 882-885

https://doi.org/10.1107/S2056989024006959

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Crystal structure of bis[(η⁵-tert-butylcyclopentadienyl)tricarbonylmolybdenum(I)](Mo—Mo)

Nigar Z. Ibrahimova,^a Dilgam B. Tagiyev,^a Iltifat U. Lyatifov,^a Mehmet Akkurt,^b Khudayar I. Hasanov ^c,^d and Ajaya Bhattarai ^e ^*

^aAcad. M. Nagiev Institute of Catalysis and Inorganic Chemistry, Ministry of Science and Education of the Azerbaijan Republic, Azerbaijan, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, ^cWestern Caspian University, Istiqlaliyyat Street 31, AZ 1001, Baku, Azerbaijan, ^dAzerbaijan Medical University, Scientific Research Centre (SRC), A. Kasumzade St. 14. AZ 1022, Baku, Azerbaijan, and ^eDepartment of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal
^*Correspondence e-mail: ajaya.bhattarai@mmamc.tu.edu.np

Edited by M. Weil, Vienna University of Technology, Austria (Received 5 June 2024; accepted 15 July 2024; online 23 July 2024)

The dinuclear molecule of the title compound, [Mo₂(C₉H₁₃)₂(CO)₆] or [Mo(^tBuCp)(CO)₃]₂ where ^tBu and Cp are tert-butyl and cyclopentadienyl, is centrosymmetric and is characterized by an Mo—Mo bond length of 3.2323 (3) Å. Imposed by inversion symmetry, the ^tBuCp and the carbonyl ligands are in a transoid arrangement to each other. In the crystal, intermolecular C—H⋯O contacts lead to the formation of layers parallel to the bc plane.

Keywords: crystal structure; Mo complex; carbonyl ligands; cyclopentadienyl ligand; tert-butyl group; carbonyl group; binuclear complex; steric effect.

CCDC reference: 2243119

1. Chemical context

Cyclopentadienyl (Cp) complexes can be employed as versatile precursors for the synthesis of new functional materials, including heterocycles, catalysts, organic conductors or pharmaceuticals (Absolonová et al., 2021 ; Kharitonov et al., 2022 ). Not only the exchange of the central metal atoms to which the Cp ligands are bound, but also the decoration of Cp ligands with functional groups can be used as a synthetic strategy to develop new catalysts (Loginov et al., 2019 ). Similarly to other coordination compounds (Mahmoudi et al., 2017a ,b ; Mahmudov & Pombeiro 2023 ), the interplay between electron-donating or -withdrawing functions of substituents with their non-covalent donor or acceptor character in cyclopentadienyl complexes can improve activity and selectivity of catalytic transformations.

In this context, we report the synthesis and crystal structure analysis of a dinuclear bis(tert-butylcyclopentadienyl)hexacarbonyldimolybdenum(I) complex, [Mo(C₉H₁₃)(CO)₃]₂ or [Mo(^tBuCp)(CO)₃]₂ (^tBu and Cp represent tert-butyl and cyclopentadienyl).

2. Structural commentary

The dinuclear title complex crystallizes in the monoclinic space group P2₁/c with half of the molecule present in the asymmetric unit (Fig. 1). The entire dimer is generated by an inversion center located at the middle of the Mo—Mo bond (Fig. 2). Imposed by inversion symmetry, the tert-butylcyclopentadienyl (^tBuCp) ligands are in a transoid arrangement about the Mo—Mo bond with that bond being 3.2323 (3) Å in length. For the tert-butyl groups on the (^tBuCp) ring, the Mo1ⁱ—Mo1—C5—C6 torsion angle is 115.30 (18)°. All bond angles involving the carbonyl ligands are close to linearity, with Mo1—C10≡O1, Mo1—C11≡O2 and Mo1—C12≡O3 being 174.6 (2), 173.1 (2) and 178.2 (2)°, respectively.

Figure 1
The asymmetric unit of the title compound, showing the labeling scheme. Displacement ellipsoids are shown at the 50% probability level.

Figure 2
The intra- and intermolecular hydrogen contacts within the crystal structure of the title compound. [Symmetry codes: (i) −x + 1, −y + 1, −z + 1; (ii) x, −y + $[{3\over 2}]$ , z + $[{1\over 2}]$ .]

The molecule of the title compound is sterically strained, which seems to be caused by short non-valent CO⋯CⁱOⁱ and ^tBuCp⋯CⁱⁱOⁱⁱ contacts, as well as steric interaction between the tert-butyl and C12≡O3 groups [symmetry codes: (i) −x + 1, −y + 1, −z + 1; (ii) x, −y + $[{3\over 2}]$ , z + $[{1\over 2}]$ ]. The C12⋯H9A and O3⋯H9A contacts have values as small as 2.65 and 2.68 Å, respectively (Fig. 2). The torsion angles C1—C5—C6—C7 and C4—C5—C6—C7 are 87.0 (3)° and −80.5 (3)°, respectively. The steric influence of the tert-butyl group is also evident in the –Mo(CO)₃– fragment with a C12—Mo1—C11 angle as small as 76.04 (11)°.

In addition, an intramolecular C—H⋯O interaction [(C4)H4⋯O2ⁱ = 2.60 Å, C4 —H4 ⋯O2ⁱ = 123°] consolidates the molecular conformation (Table 1; Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2ⁱ	0.95	2.60	3.212 (3)	123
C2—H2⋯O3ⁱⁱ	0.95	2.52	3.429 (4)	160
Symmetry codes: (i) ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

3. Supramolecular features

In the crystal of the title compound, an intermolecular C—H⋯O interaction [(C2)H2⋯O3ⁱⁱ = 2.52 Å, C2—H2⋯O3ⁱⁱ = 160°; symmetry code: (ii) x, −y + $[{3\over 2}]$ , z + $[{1\over 2}]$ ] is important and close to linear (Table 1; Figs. 2–5 ). These interactions connect the molecules into layers parallel to the bc plane (Figs. 3–5 ).

Figure 3
View of the non-classical hydrogen-bonding interactions down the a axis.

Figure 4
View of the non-classical hydrogen-bonding interactions down the b axis.

Figure 5
View of the non-classical hydrogen-bonding interactions down the c axis.

4. Database survey

A survey of the Cambridge Structural Database (CSD, Version 5.43, last update November 2022; Groom et al., 2016 ) returned 25 hits for a search with the bis[(η⁵-cyclopentadienyl)tricarbonylmolybdenum] moiety as the search criterion. The four closest similar compounds are those with refcodes CYPMOC01 (Gould et al., 1988 ), CYPMOC10 (Adams et al., 1974 ), GAKVUJ (Clegg et al., 1988 ), and TIVLAL (Hughes et al., 1996 ).

CYPMOC10 crystallizes in the monoclinic P2₁/c space group with Z = 2, CYPMOC10 and GAKVUJ crystallize in the monoclinic P2₁/n space group with Z = 2, while CYPMOC01 crystallizes in the monoclinic I2 space group with Z = 2, and TIVLAL in the triclinic P $[\overline{1}]$ space group with Z = 1.

Although the Mo—Mo distances in these structures vary slightly depending on the steric effects caused by the groups attached to the Cp rings, the values may be compared within the error limits of the experiments. The Mo—Mo distances are 3.2239 (11) Å for CYPMOC01, 3.235 (1) Å for CYPMOC10, 3.281 (1) Å for GAKVUJ, and 3.253 (1) Å for TIVLAL. The average length of the Mo—Mo bond in these structures is 3.263 (8) Å, which is in agreement with the length of the Mo—Mo bond for the title compound [3.2323 (3) Å]. In all these structures, the Mo—C≡O angles deviate only slightly from linearity due to the steric effects mentioned.

5. Synthesis and crystallization

The binuclear complex [Mo(^tBuCp)(CO)₃]₂ was synthesized according to a reported protocol (Manning et al., 1990 ). Under an inert atmosphere, 195 mg (5 mmol) of sodium amide and 0.7 ml (5 mmol) of freshly distilled tert-butylcyclopentadiene in diglyme (100 ml) were heated for 3 h at 318–323 K. After the mixture had cooled to room temperature, 1.32 g (5 mmol) of molybdenum hexacarbonyl were added and the mixture heated at 423 K for 40 min. The yellow-colored reaction mixture was cooled to room temperature and 40 g of iron(III) sulfate [Fe₂(SO₄)₃·9H₂O] in 400 ml of water and 25 ml of glacial acetic acid were added. The reaction mixture turned red, and crystals precipitated from it, which were filtered and further washed with water, methanol and pentane. After drying, 2.56 g (85%) of a dark-red crystalline solid of the title compound were obtained. Melting point: 441–442 K (with decomposition); ¹H NMR, 300 MHz, (CD₂Cl₂), δ(p.p.m.): 1.19 (s, 18H, 6CH₃), 5.02 (s, 4H, α-CH), 5.20 (s, 4H, β-CH); IR: ν(cm⁻¹): 1948, 1912 and 1858 (C≡O). Deep-red crystals of the title complex suitable for single crystal X-ray analysis were grown in toluene at a temperature of 263 K.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were included in calculated positions and treated as riding: C—H = 0.95–0.98 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	[Mo₂(C₉H₁₃)₂(CO)₆]
M_r	602.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	12.1857 (7), 8.0515 (5), 12.6153 (8)
β (°)	105.490 (2)
V (Å³)	1192.77 (13)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.09
Crystal size (mm)	0.34 × 0.27 × 0.14

Data collection
Diffractometer	Bruker D8 Quest PHOTON 100 detector
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.692, 0.845
No. of measured, independent and observed [I > 2σ(I)] reflections	13856, 2269, 1892
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.611

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.054, 1.03
No. of reflections	2269
No. of parameters	148
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.34
Computer programs: APEX4 and SAINT (Bruker, 2018 ), SHELXT (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2243119

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989024006959/wm5725sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024006959/wm5725Isup2.hkl

checkCIF report

Computing details top

Bis[(η⁵-tert-butylcyclopentadienyl)tricarbonylmolybdenum(I)](Mo—Mo) top

Crystal data top

[Mo₂(C₉H₁₃)₂(CO)₆]	F(000) = 604
M_r = 602.35	D_x = 1.677 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.1857 (7) Å	Cell parameters from 3077 reflections
b = 8.0515 (5) Å	θ = 3.0–23.6°
c = 12.6153 (8) Å	µ = 1.09 mm⁻¹
β = 105.490 (2)°	T = 150 K
V = 1192.77 (13) Å³	Prism, red
Z = 2	0.34 × 0.27 × 0.14 mm

Data collection top

Bruker D8 Quest PHOTON 100 detector diffractometer	1892 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.051
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 25.7°, θ_min = 1.7°
T_min = 0.692, T_max = 0.845	h = −11→14
13856 measured reflections	k = −8→9
2269 independent reflections	l = −15→12

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.054	w = 1/[σ²(F_o²) + (0.0188P)² + 0.5962P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2269 reflections	Δρ_max = 0.38 e Å⁻³
148 parameters	Δρ_min = −0.34 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.8160 (2)	0.5120 (3)	0.6172 (2)	0.0197 (6)
H1	0.871623	0.568453	0.590368	0.024*
C2	0.7428 (2)	0.5865 (4)	0.6739 (2)	0.0224 (7)
H2	0.741395	0.700674	0.692500	0.027*
C3	0.6726 (2)	0.4613 (3)	0.6979 (2)	0.0206 (6)
H3	0.615467	0.476238	0.735605	0.025*
C4	0.7017 (2)	0.3089 (3)	0.6559 (2)	0.0184 (6)
H4	0.666266	0.204813	0.659823	0.022*
C5	0.7923 (2)	0.3371 (3)	0.6071 (2)	0.0172 (6)
C6	0.8635 (2)	0.2032 (3)	0.5714 (2)	0.0230 (7)
C7	0.9527 (3)	0.1482 (4)	0.6762 (3)	0.0381 (9)
H7A	1.000785	0.243025	0.707718	0.057*
H7B	1.000107	0.060012	0.658058	0.057*
H7C	0.914114	0.106311	0.729745	0.057*
C8	0.7904 (3)	0.0537 (4)	0.5238 (3)	0.0491 (11)
H8A	0.838440	−0.032870	0.504889	0.074*
H8B	0.732053	0.087341	0.457472	0.074*
H8C	0.753562	0.010529	0.578296	0.074*
C9	0.9232 (4)	0.2666 (5)	0.4893 (3)	0.0625 (13)
H9A	0.866552	0.299405	0.421602	0.094*
H9B	0.971821	0.178851	0.472642	0.094*
H9C	0.970149	0.362890	0.520100	0.094*
C10	0.5452 (2)	0.3181 (3)	0.3980 (2)	0.0179 (6)
C11	0.5746 (2)	0.7073 (4)	0.4444 (2)	0.0189 (6)
C12	0.6983 (2)	0.5190 (3)	0.3786 (2)	0.0197 (6)
O1	0.50217 (16)	0.2156 (2)	0.33646 (16)	0.0251 (5)
O2	0.55213 (16)	0.8396 (2)	0.41126 (16)	0.0259 (5)
O3	0.73768 (18)	0.5429 (2)	0.30634 (17)	0.0302 (5)
Mo1	0.63311 (2)	0.48528 (3)	0.50317 (2)	0.01290 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0147 (15)	0.0257 (16)	0.0162 (14)	−0.0030 (12)	−0.0001 (11)	0.0002 (12)
C2	0.0230 (18)	0.0223 (15)	0.0169 (16)	0.0053 (13)	−0.0031 (13)	−0.0044 (12)
C3	0.0170 (16)	0.0344 (17)	0.0091 (14)	0.0089 (13)	0.0014 (11)	0.0011 (12)
C4	0.0162 (16)	0.0218 (15)	0.0156 (15)	0.0028 (12)	0.0016 (12)	0.0067 (12)
C5	0.0129 (16)	0.0212 (15)	0.0145 (15)	0.0022 (11)	−0.0015 (12)	0.0012 (11)
C6	0.0204 (17)	0.0250 (16)	0.0218 (16)	0.0099 (13)	0.0026 (13)	0.0012 (12)
C7	0.030 (2)	0.042 (2)	0.035 (2)	0.0190 (16)	−0.0021 (16)	−0.0046 (16)
C8	0.036 (2)	0.040 (2)	0.065 (3)	0.0123 (17)	0.0026 (19)	−0.0283 (19)
C9	0.079 (3)	0.054 (3)	0.077 (3)	0.040 (2)	0.061 (3)	0.029 (2)
C10	0.0174 (16)	0.0190 (15)	0.0184 (15)	0.0064 (12)	0.0064 (12)	0.0050 (12)
C11	0.0124 (16)	0.0267 (17)	0.0170 (15)	−0.0024 (12)	0.0030 (12)	−0.0021 (12)
C12	0.0197 (16)	0.0155 (15)	0.0230 (16)	0.0041 (12)	0.0039 (13)	0.0011 (12)
O1	0.0268 (12)	0.0224 (11)	0.0241 (12)	0.0005 (9)	0.0032 (9)	−0.0097 (9)
O2	0.0257 (12)	0.0156 (11)	0.0355 (13)	0.0020 (9)	0.0067 (10)	0.0072 (9)
O3	0.0413 (14)	0.0292 (12)	0.0274 (12)	0.0044 (10)	0.0216 (11)	0.0055 (9)
Mo1	0.01234 (14)	0.01388 (13)	0.01223 (13)	0.00102 (10)	0.00287 (9)	0.00043 (10)

Geometric parameters (Å, º) top

C1—C2	1.418 (4)	C6—C7	1.536 (4)
C1—C5	1.437 (4)	C7—H7A	0.9800
C1—Mo1	2.318 (3)	C7—H7B	0.9800
C1—H1	0.9500	C7—H7C	0.9800
C2—C3	1.406 (4)	C8—H8A	0.9800
C2—Mo1	2.357 (3)	C8—H8B	0.9800
C2—H2	0.9500	C8—H8C	0.9800
C3—C4	1.419 (4)	C9—H9A	0.9800
C3—Mo1	2.381 (3)	C9—H9B	0.9800
C3—H3	0.9500	C9—H9C	0.9800
C4—C5	1.419 (4)	C10—O1	1.158 (3)
C4—Mo1	2.360 (3)	C10—Mo1	1.990 (3)
C4—H4	0.9500	C11—O2	1.151 (3)
C5—C6	1.525 (4)	C11—Mo1	1.992 (3)
C5—Mo1	2.356 (3)	C12—O3	1.154 (3)
C6—C9	1.505 (4)	C12—Mo1	1.960 (3)
C6—C8	1.522 (4)

C2—C1—C5	108.7 (2)	C6—C8—H8B	109.5
C2—C1—Mo1	73.84 (15)	H8A—C8—H8B	109.5
C5—C1—Mo1	73.53 (15)	C6—C8—H8C	109.5
C2—C1—H1	125.6	H8A—C8—H8C	109.5
C5—C1—H1	125.6	H8B—C8—H8C	109.5
Mo1—C1—H1	118.8	C6—C9—H9A	109.5
C3—C2—C1	107.8 (2)	C6—C9—H9B	109.5
C3—C2—Mo1	73.69 (15)	H9A—C9—H9B	109.5
C1—C2—Mo1	70.87 (15)	C6—C9—H9C	109.5
C3—C2—H2	126.1	H9A—C9—H9C	109.5
C1—C2—H2	126.1	H9B—C9—H9C	109.5
Mo1—C2—H2	121.1	O1—C10—Mo1	174.6 (2)
C2—C3—C4	108.2 (3)	O2—C11—Mo1	173.1 (2)
C2—C3—Mo1	71.79 (15)	O3—C12—Mo1	178.2 (2)
C4—C3—Mo1	71.76 (15)	C12—Mo1—C10	79.64 (11)
C2—C3—H3	125.9	C12—Mo1—C11	76.04 (11)
C4—C3—H3	125.9	C10—Mo1—C11	106.46 (11)
Mo1—C3—H3	122.2	C12—Mo1—C1	87.50 (11)
C3—C4—C5	108.9 (2)	C10—Mo1—C1	137.22 (10)
C3—C4—Mo1	73.42 (15)	C11—Mo1—C1	109.68 (10)
C5—C4—Mo1	72.33 (15)	C12—Mo1—C5	93.81 (10)
C3—C4—H4	125.5	C10—Mo1—C5	104.20 (10)
C5—C4—H4	125.5	C11—Mo1—C5	145.19 (10)
Mo1—C4—H4	120.4	C1—Mo1—C5	35.79 (9)
C4—C5—C1	106.2 (2)	C12—Mo1—C2	115.65 (11)
C4—C5—C6	125.8 (2)	C10—Mo1—C2	156.39 (10)
C1—C5—C6	127.1 (3)	C11—Mo1—C2	95.11 (10)
C4—C5—Mo1	72.64 (14)	C1—Mo1—C2	35.29 (9)
C1—C5—Mo1	70.68 (14)	C5—Mo1—C2	58.97 (9)
C6—C5—Mo1	129.98 (18)	C12—Mo1—C4	127.37 (10)
C9—C6—C8	109.7 (3)	C10—Mo1—C4	98.49 (10)
C9—C6—C5	112.4 (2)	C11—Mo1—C4	149.01 (10)
C8—C6—C5	110.9 (2)	C1—Mo1—C4	58.45 (10)
C9—C6—C7	109.3 (3)	C5—Mo1—C4	35.03 (9)
C8—C6—C7	108.5 (3)	C2—Mo1—C4	58.06 (10)
C5—C6—C7	106.1 (2)	C12—Mo1—C3	145.58 (11)
C6—C7—H7A	109.5	C10—Mo1—C3	123.87 (10)
C6—C7—H7B	109.5	C11—Mo1—C3	114.21 (10)
H7A—C7—H7B	109.5	C1—Mo1—C3	58.09 (10)
C6—C7—H7C	109.5	C5—Mo1—C3	58.36 (9)
H7A—C7—H7C	109.5	C2—Mo1—C3	34.52 (10)
H7B—C7—H7C	109.5	C4—Mo1—C3	34.82 (9)
C6—C8—H8A	109.5

C5—C1—C2—C3	−0.9 (3)	C2—C1—C5—C4	1.6 (3)
Mo1—C1—C2—C3	64.91 (18)	Mo1—C1—C5—C4	−64.44 (17)
C5—C1—C2—Mo1	−65.81 (18)	C2—C1—C5—C6	−167.9 (2)
C1—C2—C3—C4	−0.1 (3)	Mo1—C1—C5—C6	126.0 (3)
Mo1—C2—C3—C4	62.92 (18)	C2—C1—C5—Mo1	66.01 (18)
C1—C2—C3—Mo1	−63.06 (18)	C4—C5—C6—C9	160.1 (3)
C2—C3—C4—C5	1.2 (3)	C1—C5—C6—C9	−32.3 (4)
Mo1—C3—C4—C5	64.09 (18)	Mo1—C5—C6—C9	63.0 (4)
C2—C3—C4—Mo1	−62.93 (19)	C4—C5—C6—C8	37.0 (4)
C3—C4—C5—C1	−1.7 (3)	C1—C5—C6—C8	−155.4 (3)
Mo1—C4—C5—C1	63.12 (17)	Mo1—C5—C6—C8	−60.1 (3)
C3—C4—C5—C6	168.0 (2)	C4—C5—C6—C7	−80.5 (3)
Mo1—C4—C5—C6	−127.2 (3)	C1—C5—C6—C7	87.0 (3)
C3—C4—C5—Mo1	−64.78 (18)	Mo1—C5—C6—C7	−177.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.95	2.60	3.212 (3)	123
C2—H2···O3ⁱⁱ	0.95	2.52	3.429 (4)	160

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z+1/2.

Acknowledgements

This work was supported by the Acad. M. Nagiev Institute of Catalysis and Inorganic Chemistry, Ministry of Science and Education of the Azerbaijan Republic, Western Caspian University (Azerbaijan) and Azerbaijan Medical University. The authors′ contributions are as follows. Conceptualization, IUL, MA and AB; synthesis, NZI and IUL; X-ray analysis, IUL and KIH; writing (review and editing of the manuscript) IUL and MA; funding acquisition, NZI, DBT, IUL and KIH; supervision, IUL, MA and AB.

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