Crystal structure and Hirshfeld surface analysis of 3-benzoyl-6-(1,3-dioxo-1-phenyl­butan-2-yl)-2-hy­droxy-2-methyl-4-phenyl­cyclo­hexane-1,1-dicarbo­nitrile

Naghiyev, F.N.; Khrustalev, V.N.; Dobrokhotova, E.V.; Akkurt, M.; Khalilov, A.N.; Bhattarai, A.; Mamedov, İ.G.

doi:10.1107/S2056989022004777

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ISSN: 2056-9890

Volume 78| Part 6| June 2022| Pages 568-573

https://doi.org/10.1107/S2056989022004777

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Crystal structure and Hirshfeld surface analysis of 3-benzoyl-6-(1,3-dioxo-1-phenylbutan-2-yl)-2-hydroxy-2-methyl-4-phenylcyclohexane-1,1-dicarbonitrile

Farid N. Naghiyev,^a Victor N. Khrustalev,^b,^c Ekaterina V. Dobrokhotova,^b Mehmet Akkurt,^d Ali N. Khalilov,^e,^a Ajaya Bhattarai ^f ^* and İbrahim G. Mamedov ^a

^aDepartment of Chemistry, Baku State University, Z. Khalilov str. 23, Az 1148, Baku, Azerbaijan, ^bPeoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St. 6, Moscow 117198, Russian Federation, ^cN. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow 119991, Russian Federation, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^e`Composite Materials' Scientific Research Center, Azerbaijan State Economic University (UNEC), H. Aliyev str. 135, Az 1063, Baku, Azerbaijan, and ^fDepartment 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 11 April 2022; accepted 4 May 2022; online 13 May 2022)

The central cyclohexane ring of the title compound, C₃₂H₂₈N₂O₄, adopts a chair conformation, with puckering parameters Q_T = 0.618 (2) Å, θ = 176.72 (19)° and φ = 290 (3)°. In the crystal, molecules are linked by O—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds, forming layers parallel to (100). These layers are linked by weak C—H⋯π interactions and van der Waals forces. A Hirshfeld surface analysis indicates that the contributions from the most prevalent interactions are H⋯H (41.2% contribution), C⋯H/H⋯C (20.3%), O⋯H/H⋯O (17.8%) and N⋯H/H⋯N (10.6%).

Keywords: crystal structure; cyclohexane conformation; hydrogen bond; van der Waals forces; Hirshfeld surface analysis.

CCDC reference: 2170547

1. Chemical context

Functionalized derivatives of carbo- and heterocyclic compounds are of great interest in the fields of organic synthesis, catalysis, materials science and medicinal chemistry (Zubkov et al., 2018 ; Shikhaliyev et al., 2019 ; Viswanathan et al., 2019 ; Gurbanov et al., 2020 ; Khalilov et al., 2021 ). In particular, β-dicarbonyl compounds are important chemical substrates for the construction of various classes of organic compounds (Kaur et al., 2021 ).

To the best of our knowledge, the interaction of β-dicarbonyl compounds with phenyl–allylidene–malononitriles leads to the formation of xanthene, benzo[b]pyran and pyridine derivatives (Bardasov et al., 2014 ; Amoozadeh et al., 2018 ). Interestingly, we discovered that in case of the reaction of one equivalent of phenyl–allylidene–malononitrile with two equivalents of benzoylacetone at room temperature, a substituted cyclohexane derivative was the product. In the context of ongoing structural studies (Safavora et al., 2019 ; Aliyeva et al., 2011 ; Mamedov et al., 2022 ), we report here the crystal structure and Hirshfeld surface analysis of the title compound, 3-benzoyl-6-(1,3-dioxo-1-phenylbutan-2-yl)-2-hydroxy-2-methyl-4-phenylcyclohexane-1,1-dicarbonitrile.

2. Structural commentary

In the title compound (Fig. 1), the central cyclohexane ring (A: atoms C1–C6) adopts a chair conformation, with puckering parameters (Cremer & Pople, 1975 ) Q_T = 0.618 (2) Å, θ = 176.72 (19)° and φ = 290 (3)°. The phenyl (B: C11–C16; C: C21–C26; D: C27–C32) rings make dihedral angles of 78.23 (10), 83.20 (11) and 82.09 (10)°, respectively, with the mean plane of the central cyclohexane ring. The dihedral angles between the phenyl rings are B/C = 21.88 (10)°, B/D = 21.88 (19)° and C/D = 73.64 (10)°. The C1—C7—C10—C11, C1—C7—C10—O2, C1—C7—C8—C9 and C1—C7—C8—O1 torsion angles are −157.13 (16), 27.9 (2), −73.6 (2) and 106.7 (2)°. The phenyl, benzoyl, hydroxy, cyano C2—C17≡N1 and 1,3-dioxo-1-phenylbutan-2-yl substituents all occupy equatorial sites, so that the cyano C2—C18≡N2 substituent necessarily occupies an axial site. There are five stereogenic centres and the chirality about the C1, C3, C4, C5 and C7 atoms are S, R, R, S and R, respectively. The values of the geometric parameters of the title compound are normal and compatible with those of related compounds compiled in the Database survey section (§5).

Figure 1
The molecular structure of the title compound, showing the labelling scheme and displacement ellipsoids drawn at the 30% probability level.

3. Supramolecular features

In the crystal, O—H⋯O hydrogen bonds of medium strength, and weaker C—H⋯O and C—H⋯N interactions link adjacent molecules, forming layers extending parallel to (100) (Table 1 and Figs. 2–4 ). These layers are connected by weak C—H⋯π interactions and van der Waals interactions (Table 1 and Fig. 5).

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C27–C32 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1ⁱ	0.94 (3)	1.89 (3)	2.787 (2)	159 (3)
C1—H1⋯N1ⁱ	1.00	2.50	3.466 (3)	163
C12—H12⋯O4ⁱⁱ	0.95	2.58	3.242 (3)	127
C28—H28⋯O2ⁱⁱ	0.95	2.40	3.319 (2)	164
C14—H14⋯Cg4ⁱⁱⁱ	0.95	2.80	3.475 (2)	129
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x+1, y, z.

Figure 2
A view of the molecular packing down [100], showing O—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds as dashed lines.

Figure 3
A view of the molecular packing down [010]. Intermolecular interactions are depicted as in Fig. 2

Figure 4
A view of the molecular packing down [001]. Intermolecular interactions are depicted as in Fig. 2

Figure 5
The crystal packing viewed down [010], showing O—H⋯O, C—H⋯O, C—H⋯N hydrogen bonds and C—H⋯π interactions.

4. Hirshfeld surface analysis

A Hirshfeld surface for the title compound and its associated two-dimensional fingerprint plots were analyzed and calculated using CrystalExplorer (Version 17.5; Turner et al., 2017 ). Hirshfeld surfaces allow for the display of intermolecular interactions by using distinct colours and intensities to indicate short and long contacts, as well as the relative strengths of the interactions. The three-dimensional (3D) Hirshfeld surface of the title compound plotted over d_norm in the range from −0.5877 to +1.7202 a.u. is shown in Fig. 6. As discussed above, the O3—H3⋯O1 interactions play a key role in the molecular packing of the title compound.

Figure 6
(a) Front and (b) back sides of the 3D Hirshfeld surface of the title compound plotted over d_norm in the range from −0.5877 to +1.7202 a.u.

The overall two-dimensional (2D) fingerprint plot [Fig. 7(a)] and those delineated into H⋯H (41.2% contribution), C⋯H/H⋯C (20.3%), O⋯H/H⋯O (17.8%) and N⋯H/H⋯N (10.6%) contacts are illustrated in Figs. 7(b)–(e), respectively. The other minor contributions to the Hirshfeld surface are from N⋯C/C⋯N (1.0%), C⋯C (0.9%), O⋯N/N⋯O (0.8%) and O⋯C/C⋯O (0.8%) contacts. The large number of H⋯H, C⋯H/H⋯C, O⋯H/H⋯O and N⋯H/H⋯N interactions suggest that van der Waals interactions and hydrogen bonding play major roles in the crystal packing. Various interatomic contacts are compiled in Table 2.

Table 2
Summary of short interatomic contacts (Å) in the title compound

Contact	Distance	Symmetry operation
O1⋯H3	1.89	1 − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z
H9A⋯H6A	2.39	1 − x, 1 − y, − z
O4⋯H15	2.73	−1 + x, y, z
H19B⋯N1	2.77	1 − x, 1 − y, 1 − z
H26⋯H31	2.37	x, $[{1\over 2}]$ − y, $[{1\over 2}]$ + z
C25⋯C24	3.367	−x, 1 − y, 1 − z
H29⋯H23	2.41	x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z
H13⋯H15	2.36	2 − x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z

Figure 7
A view of the 2D fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) C⋯H/H⋯C, (d) O⋯H/H⋯O and (e) N⋯H/H⋯N interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

5. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.42, update of September 2021; Groom et al., 2016 ) for the 2-hydroxy-2-methylcyclohexane-1,1-dicarbonitrile moiety revealed five structures closely related to the title compound: 3-cyano-4-hydroxy-2-(4-methylphenyl)-6-oxo-N-phenyl-4-(thiophen-2-yl)cyclohexane-1-carboxamide hydrate (CSD refcode UPOMOE; Naghiyev et al., 2021 ), (2RS,3SR,4RS,6SR)-3-benzoyl-4-hydroxy-2,4,6-triphenylcyclohexane-1,1-dicarbonitrile (MEHMOC01; Rodríguez et al., 2008 ), 3-(4-fluorobenzoyl)-4-(4-fluorophenyl)-4-hydroxy-2,6-diphenylcyclohexane-1,1-dicarbonitrile (SODHAW; Narayana et al., 2014 ), 5-cyano-2-hydroxy-2-methyl-N-phenyl-4-(pyridin-4-yl)-6-(thiophen-2-yl)-3,4-dihydro-2H-pyran-3-carboxamide (JUPHUA; Naghiyev et al., 2020 ) and 5-cyano-2-hydroxy-2-methyl-6-oxo-N-phenyl-4-(thiophen-2-yl)piperidine-3-carboxamide methanol solvate (JUPJOW; Naghiyev et al., 2020).

In the crystal of UPOMOE, the central cyclohexane ring adopts a chair conformation. Molecules are linked by N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds, forming layers parallel to (100), which interact via the van der Waals forces between them.

In the crystal of MEHMOC01, the molecules are linked into complex sheets by two C—H⋯O hydrogen bonds and three C—H⋯N hydrogen bonds.

In the crystal of SODHAW, molecules are linked via pairs of O—H⋯N hydrogen bonds, forming inversion dimers. The dimers are linked via C—H⋯N and C—H⋯O hydrogen bonds, forming chains parallel to [001]. C—H⋯F hydrogen bonds link the chains into sheets lying parallel to (100).

In JUPHUA, the crystal structure is stabilized by an extensive hydrogen-bonding network defined by N—H⋯N, O—H⋯N and C—H⋯O interactions with graph-set motifs C(9), C(8), C₄⁴(32) and R₆⁶(48), with base vectors [100], [011] and [110] for the 3D network.

In JUPJOW, the crystal structure is also stabilized by an extensive hydrogen-bonding network of N—H⋯O, O—H⋯O and O—H⋯N interactions, where the methanol molecule participate with neighbouring molecules with graph-set motifs C(4), C₂²(10), C₄⁴(28), R₂²(8) and R₆⁶(36), with base vectors [010], [100] and [001] for the 3D network. For JUPHUA and JUPJOW, another non-covalent weak interaction is also observed, specifically a chalcogen⋯π interaction (ca 3.6 Å) in JUPHUA between the thiophenyl sulfur fragment and the phenyl ring and a hydrogen⋯π interaction (ca 3.2 Å) in JUPJOW between the methyl group on the piperidone ring and the phenyl ring.

6. Synthesis and crystallization

To a solution of 2-(3-phenylallylidene)malononitrile (0.92 g, 5 mmol) and benzoylacetone (1.68 g, 10 mmol) in benzene (25 ml), 3–4 drops of 1-methylpiperazine were added and the mixture was stirred for 10 min and kept at room temperature for 72 h. Benzene (15 ml) was then removed from the reaction mixture by distillation, which was left overnight. The crystals which formed were separated by filtration and recrystallized from an ethanol–water (1:1 v/v) solution (yield 41%; m.p. 514–515 K).

¹H NMR (300 MHz, DMSO-d₆, ppm): δ 1.74 (s, 3H, CH₃), 2.01 (t, 2H, CH₂), 2.12 (s, 3H, COCH₃), 3.47 (d–d, 1H, CH), 3.52 (s, 1H, OH), 4.08 (m, 1H, CH), 4.62 (d, 1H, CH), 4.86 (d, 1H, CH), 7.12–7.78 (m, 15H, 15Ar-H). ¹³C NMR (75 MHz, DMSO-d₆, ppm): δ 24.28 (CH₃), 30.36 (COCH₃), 34.42 (CH₂), 39.41 (CH), 45.49 (CH), 56.46 (C_tert), 57.01 (CH), 60.85 (CH), 81.92 (O—C_tert), 111.37 (CN), 111.81 (CN), 125.94 (CH_arom), 127.22 (2CH_arom), 127.86 (2CH_arom), 128.90 (2CH_arom), 128.98 (2CH_arom), 129.31 (2CH_arom), 130.35 (2CH_arom), 132.52 (CH_arom), 133.85 (CH_arom), 135.44 (C_arom), 138.49 (C_arom), 141.22 (C_arom), 194.97 (C=O), 195.93 (C=O), 200.21 (C=O).

7. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 3. Due to large differences between calculated and observed intensities, about 40 reflections were omitted from the refinement. The H atom of the OH group was located in a difference map and its positional parameters were allowed to refine freely [O3—H3 = 0.93 (3) Å], with U_iso(H) = 1.5U_eq(O). All H atoms bound to C atoms were positioned geometrically and refined as riding, with C—H = 0.95 (aromatic), 0.99 (methylene), 1.00 (methine) and 0.98 Å (methyl), with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for the others.

Table 3
Experimental details

Crystal data
Chemical formula	C₃₂H₂₈N₂O₄
M_r	504.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.9798 (3), 11.8411 (2), 15.7406 (3)
β (°)	91.901 (2)
V (Å³)	2604.21 (9)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.69
Crystal size (mm)	0.09 × 0.06 × 0.06

Data collection
Diffractometer	Rigaku XtaLAB Synergy Dualflex HyPix
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Tokyo, Japan.]$ )
T_min, T_max	0.933, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	77914, 5618, 5497
R_int	0.110
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.187, 1.11
No. of reflections	5618
No. of parameters	348
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.33
Computer programs: CrysAlis PRO (Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Tokyo, Japan.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2170547

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989022004777/wm5643sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989022004777/wm5643Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989022004777/wm5643Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

3-Benzoyl-6-(1,3-dioxo-1-phenylbutan-2-yl)-2-hydroxy-2-methyl-4-phenylcyclohexane-1,1-dicarbonitrile top

Crystal data top

C₃₂H₂₈N₂O₄	F(000) = 1064
M_r = 504.56	D_x = 1.287 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 13.9798 (3) Å	Cell parameters from 52541 reflections
b = 11.8411 (2) Å	θ = 3.1–79.4°
c = 15.7406 (3) Å	µ = 0.69 mm⁻¹
β = 91.901 (2)°	T = 100 K
V = 2604.21 (9) Å³	Prism, colourless
Z = 4	0.09 × 0.06 × 0.06 mm

Data collection top

Rigaku XtaLAB Synergy Dualflex HyPix diffractometer	5497 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.110
φ and ω scans	θ_max = 80.3°, θ_min = 4.7°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021)	h = −17→17
T_min = 0.933, T_max = 0.949	k = −14→12
77914 measured reflections	l = −20→20
5618 independent reflections

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.074	Hydrogen site location: mixed
wR(F²) = 0.187	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0869P)² + 2.2708P] where P = (F_o² + 2F_c²)/3
5618 reflections	(Δ/σ)_max < 0.001
348 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.33 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
O1	0.60930 (11)	0.56945 (13)	0.06669 (10)	0.0327 (3)
O2	0.68557 (10)	0.25976 (12)	0.19898 (9)	0.0290 (3)
O3	0.42148 (11)	0.24428 (13)	0.31883 (10)	0.0324 (3)
H3	0.415 (2)	0.199 (3)	0.367 (2)	0.049*
O4	0.20303 (11)	0.28810 (13)	0.28805 (10)	0.0351 (4)
N1	0.52004 (13)	0.62769 (17)	0.35886 (12)	0.0344 (4)
N2	0.65726 (13)	0.31942 (18)	0.39833 (12)	0.0368 (4)
C1	0.52388 (13)	0.39859 (16)	0.21623 (12)	0.0231 (4)
H1	0.5225	0.3158	0.2038	0.028*
C2	0.51310 (13)	0.41460 (17)	0.31391 (12)	0.0240 (4)
C3	0.41622 (13)	0.35964 (18)	0.34400 (12)	0.0266 (4)
C4	0.33213 (13)	0.42000 (17)	0.29384 (12)	0.0237 (4)
H4	0.3342	0.5025	0.3074	0.028*
C5	0.34164 (13)	0.40464 (16)	0.19736 (12)	0.0236 (4)
H5	0.3408	0.3219	0.1846	0.028*
C6	0.43762 (13)	0.45324 (17)	0.16959 (12)	0.0244 (4)
H6A	0.4432	0.4417	0.1077	0.029*
H6B	0.4386	0.5356	0.1805	0.029*
C7	0.62107 (13)	0.44637 (16)	0.18714 (12)	0.0237 (4)
H7	0.6368	0.5172	0.2193	0.028*
C8	0.61386 (13)	0.47219 (17)	0.09111 (12)	0.0261 (4)
C9	0.61333 (15)	0.3741 (2)	0.03178 (13)	0.0320 (4)
H9A	0.5778	0.3941	−0.0208	0.048*
H9B	0.5825	0.3095	0.0585	0.048*
H9C	0.6793	0.3543	0.0187	0.048*
C10	0.70293 (13)	0.36013 (16)	0.20056 (12)	0.0235 (4)
C11	0.80373 (13)	0.40261 (17)	0.20804 (12)	0.0255 (4)
C12	0.82669 (14)	0.51657 (19)	0.20982 (14)	0.0308 (4)
H12	0.7773	0.5717	0.2078	0.037*
C13	0.92204 (15)	0.5500 (2)	0.21452 (15)	0.0352 (5)
H13	0.9376	0.6281	0.2152	0.042*
C14	0.99465 (15)	0.4702 (2)	0.21823 (15)	0.0364 (5)
H14	1.0597	0.4935	0.2220	0.044*
C15	0.97192 (15)	0.3563 (2)	0.21636 (17)	0.0403 (6)
H15	1.0215	0.3015	0.2188	0.048*
C16	0.87744 (15)	0.32241 (19)	0.21094 (15)	0.0346 (5)
H16	0.8623	0.2442	0.2092	0.041*
C17	0.51666 (13)	0.53547 (18)	0.33812 (12)	0.0257 (4)
C18	0.59353 (14)	0.35950 (18)	0.36132 (12)	0.0269 (4)
C19	0.40934 (15)	0.3705 (2)	0.43962 (13)	0.0343 (5)
H19A	0.4054	0.4505	0.4550	0.051*
H19B	0.4662	0.3368	0.4675	0.051*
H19C	0.3520	0.3311	0.4581	0.051*
C20	0.23709 (13)	0.37142 (17)	0.32275 (12)	0.0254 (4)
C21	0.19117 (14)	0.42334 (19)	0.39784 (13)	0.0301 (4)
C22	0.20292 (16)	0.5357 (2)	0.41997 (16)	0.0403 (5)
H22	0.2385	0.5844	0.3849	0.048*
C23	0.16292 (19)	0.5777 (3)	0.4932 (2)	0.0582 (8)
H23	0.1697	0.6553	0.5074	0.070*
C24	0.1136 (2)	0.5067 (4)	0.54509 (18)	0.0669 (10)
H24	0.0878	0.5351	0.5959	0.080*
C25	0.1012 (2)	0.3952 (4)	0.5241 (2)	0.0663 (10)
H25	0.0675	0.3465	0.5606	0.080*
C26	0.13807 (17)	0.3531 (3)	0.44923 (17)	0.0457 (6)
H26	0.1270	0.2767	0.4333	0.055*
C27	0.26091 (13)	0.46041 (17)	0.14557 (12)	0.0243 (4)
C28	0.23681 (13)	0.57302 (17)	0.15741 (13)	0.0261 (4)
H28	0.2681	0.6150	0.2016	0.031*
C29	0.16717 (14)	0.62547 (19)	0.10523 (13)	0.0297 (4)
H29	0.1507	0.7022	0.1147	0.036*
C30	0.12222 (14)	0.5654 (2)	0.03973 (14)	0.0330 (5)
H30	0.0756	0.6011	0.0035	0.040*
C31	0.14567 (15)	0.4533 (2)	0.02747 (14)	0.0346 (5)
H31	0.1149	0.4119	−0.0173	0.042*
C32	0.21395 (15)	0.40056 (19)	0.08018 (13)	0.0301 (4)
H32	0.2287	0.3232	0.0716	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0331 (8)	0.0336 (8)	0.0315 (8)	0.0030 (6)	0.0039 (6)	0.0075 (6)
O2	0.0234 (7)	0.0273 (7)	0.0364 (8)	0.0000 (5)	0.0006 (5)	0.0033 (6)
O3	0.0323 (8)	0.0267 (7)	0.0385 (8)	−0.0003 (6)	0.0031 (6)	0.0060 (6)
O4	0.0280 (7)	0.0334 (8)	0.0444 (9)	−0.0061 (6)	0.0048 (6)	−0.0021 (7)
N1	0.0320 (9)	0.0354 (10)	0.0355 (9)	0.0023 (7)	−0.0010 (7)	−0.0007 (8)
N2	0.0290 (9)	0.0458 (11)	0.0353 (10)	0.0044 (8)	−0.0025 (7)	0.0073 (8)
C1	0.0188 (8)	0.0272 (9)	0.0234 (9)	−0.0002 (7)	0.0000 (6)	0.0028 (7)
C2	0.0198 (8)	0.0288 (10)	0.0233 (9)	0.0014 (7)	−0.0017 (7)	0.0021 (7)
C3	0.0215 (9)	0.0329 (10)	0.0255 (9)	0.0000 (7)	0.0005 (7)	0.0063 (8)
C4	0.0197 (8)	0.0279 (9)	0.0236 (9)	0.0002 (7)	0.0009 (7)	0.0011 (7)
C5	0.0195 (8)	0.0276 (9)	0.0236 (9)	−0.0009 (7)	−0.0003 (6)	0.0014 (7)
C6	0.0207 (8)	0.0319 (10)	0.0204 (8)	0.0006 (7)	0.0006 (6)	0.0034 (7)
C7	0.0193 (8)	0.0270 (9)	0.0248 (9)	0.0007 (7)	0.0002 (6)	0.0028 (7)
C8	0.0166 (8)	0.0338 (10)	0.0280 (9)	0.0010 (7)	0.0026 (6)	0.0046 (8)
C9	0.0304 (10)	0.0407 (12)	0.0250 (9)	0.0034 (8)	0.0017 (8)	0.0022 (8)
C10	0.0209 (8)	0.0272 (9)	0.0225 (8)	0.0020 (7)	0.0011 (6)	0.0030 (7)
C11	0.0199 (8)	0.0318 (10)	0.0248 (9)	0.0022 (7)	0.0009 (7)	0.0029 (7)
C12	0.0230 (9)	0.0331 (11)	0.0361 (11)	0.0012 (8)	−0.0006 (7)	0.0009 (8)
C13	0.0245 (10)	0.0347 (11)	0.0462 (12)	−0.0045 (8)	−0.0024 (8)	−0.0007 (9)
C14	0.0193 (9)	0.0457 (13)	0.0441 (12)	−0.0019 (8)	−0.0011 (8)	0.0112 (10)
C15	0.0216 (10)	0.0410 (13)	0.0585 (15)	0.0064 (8)	0.0042 (9)	0.0166 (11)
C16	0.0228 (9)	0.0328 (11)	0.0482 (13)	0.0028 (8)	0.0027 (8)	0.0112 (9)
C17	0.0196 (8)	0.0335 (11)	0.0238 (9)	0.0016 (7)	−0.0016 (6)	0.0025 (7)
C18	0.0235 (9)	0.0335 (10)	0.0235 (9)	0.0007 (7)	0.0006 (7)	0.0045 (8)
C19	0.0251 (10)	0.0536 (13)	0.0242 (10)	0.0017 (9)	0.0007 (7)	0.0010 (9)
C20	0.0226 (9)	0.0269 (9)	0.0266 (9)	0.0015 (7)	0.0002 (7)	0.0047 (7)
C21	0.0187 (8)	0.0427 (12)	0.0289 (10)	0.0045 (8)	0.0020 (7)	0.0038 (8)
C22	0.0237 (10)	0.0520 (14)	0.0453 (13)	0.0038 (9)	0.0017 (9)	−0.0153 (11)
C23	0.0311 (12)	0.088 (2)	0.0552 (17)	0.0090 (13)	0.0003 (11)	−0.0338 (16)
C24	0.0444 (15)	0.121 (3)	0.0360 (13)	0.0343 (18)	0.0033 (11)	−0.0123 (16)
C25	0.0412 (15)	0.112 (3)	0.0469 (16)	0.0273 (16)	0.0208 (12)	0.0340 (18)
C26	0.0336 (12)	0.0575 (16)	0.0470 (14)	0.0113 (10)	0.0145 (10)	0.0213 (12)
C27	0.0181 (8)	0.0312 (10)	0.0236 (9)	−0.0027 (7)	0.0015 (6)	0.0025 (7)
C28	0.0222 (9)	0.0288 (10)	0.0271 (9)	−0.0025 (7)	−0.0007 (7)	0.0017 (7)
C29	0.0236 (9)	0.0322 (10)	0.0333 (10)	0.0007 (8)	0.0002 (7)	0.0045 (8)
C30	0.0225 (9)	0.0446 (12)	0.0315 (10)	0.0006 (8)	−0.0037 (7)	0.0076 (9)
C31	0.0267 (10)	0.0446 (12)	0.0321 (10)	−0.0014 (9)	−0.0076 (8)	−0.0044 (9)
C32	0.0261 (9)	0.0340 (11)	0.0300 (10)	0.0012 (8)	−0.0023 (8)	−0.0039 (8)

Geometric parameters (Å, º) top

O1—C8	1.215 (3)	C12—H12	0.9500
O2—C10	1.213 (2)	C13—C14	1.387 (3)
O3—C3	1.425 (3)	C13—H13	0.9500
O3—H3	0.93 (3)	C14—C15	1.386 (4)
O4—C20	1.217 (3)	C14—H14	0.9500
N1—C17	1.140 (3)	C15—C16	1.380 (3)
N2—C18	1.151 (3)	C15—H15	0.9500
C1—C6	1.534 (2)	C16—H16	0.9500
C1—C7	1.555 (2)	C19—H19A	0.9800
C1—C2	1.561 (3)	C19—H19B	0.9800
C1—H1	1.0000	C19—H19C	0.9800
C2—C18	1.480 (3)	C20—C21	1.496 (3)
C2—C17	1.481 (3)	C21—C22	1.384 (3)
C2—C3	1.589 (3)	C21—C26	1.392 (3)
C3—C19	1.517 (3)	C22—C23	1.390 (4)
C3—C4	1.567 (3)	C22—H22	0.9500
C4—C20	1.531 (3)	C23—C24	1.374 (6)
C4—C5	1.540 (3)	C23—H23	0.9500
C4—H4	1.0000	C24—C25	1.370 (6)
C5—C27	1.521 (3)	C24—H24	0.9500
C5—C6	1.537 (3)	C25—C26	1.393 (4)
C5—H5	1.0000	C25—H25	0.9500
C6—H6A	0.9900	C26—H26	0.9500
C6—H6B	0.9900	C27—C28	1.389 (3)
C7—C8	1.542 (3)	C27—C32	1.396 (3)
C7—C10	1.543 (3)	C28—C29	1.398 (3)
C7—H7	1.0000	C28—H28	0.9500
C8—C9	1.490 (3)	C29—C30	1.386 (3)
C9—H9A	0.9800	C29—H29	0.9500
C9—H9B	0.9800	C30—C31	1.383 (3)
C9—H9C	0.9800	C30—H30	0.9500
C10—C11	1.497 (3)	C31—C32	1.392 (3)
C11—C12	1.387 (3)	C31—H31	0.9500
C11—C16	1.401 (3)	C32—H32	0.9500
C12—C13	1.390 (3)

C3—O3—H3	108 (2)	C13—C12—H12	120.0
C6—C1—C7	112.72 (15)	C14—C13—C12	120.5 (2)
C6—C1—C2	108.66 (15)	C14—C13—H13	119.8
C7—C1—C2	111.08 (15)	C12—C13—H13	119.8
C6—C1—H1	108.1	C15—C14—C13	119.7 (2)
C7—C1—H1	108.1	C15—C14—H14	120.2
C2—C1—H1	108.1	C13—C14—H14	120.2
C18—C2—C17	106.12 (16)	C16—C15—C14	120.2 (2)
C18—C2—C1	110.26 (16)	C16—C15—H15	119.9
C17—C2—C1	111.54 (16)	C14—C15—H15	119.9
C18—C2—C3	108.05 (15)	C15—C16—C11	120.4 (2)
C17—C2—C3	109.92 (16)	C15—C16—H16	119.8
C1—C2—C3	110.78 (15)	C11—C16—H16	119.8
O3—C3—C19	111.25 (17)	N1—C17—C2	178.2 (2)
O3—C3—C4	110.00 (16)	N2—C18—C2	178.2 (2)
C19—C3—C4	112.97 (17)	C3—C19—H19A	109.5
O3—C3—C2	104.92 (15)	C3—C19—H19B	109.5
C19—C3—C2	110.11 (16)	H19A—C19—H19B	109.5
C4—C3—C2	107.20 (15)	C3—C19—H19C	109.5
C20—C4—C5	110.67 (15)	H19A—C19—H19C	109.5
C20—C4—C3	108.84 (15)	H19B—C19—H19C	109.5
C5—C4—C3	110.81 (15)	O4—C20—C21	121.07 (18)
C20—C4—H4	108.8	O4—C20—C4	120.11 (18)
C5—C4—H4	108.8	C21—C20—C4	118.68 (17)
C3—C4—H4	108.8	C22—C21—C26	119.3 (2)
C27—C5—C6	108.92 (15)	C22—C21—C20	122.9 (2)
C27—C5—C4	112.99 (15)	C26—C21—C20	117.7 (2)
C6—C5—C4	109.95 (15)	C21—C22—C23	120.4 (3)
C27—C5—H5	108.3	C21—C22—H22	119.8
C6—C5—H5	108.3	C23—C22—H22	119.8
C4—C5—H5	108.3	C24—C23—C22	119.8 (3)
C1—C6—C5	112.69 (15)	C24—C23—H23	120.1
C1—C6—H6A	109.1	C22—C23—H23	120.1
C5—C6—H6A	109.1	C25—C24—C23	120.5 (3)
C1—C6—H6B	109.1	C25—C24—H24	119.7
C5—C6—H6B	109.1	C23—C24—H24	119.7
H6A—C6—H6B	107.8	C24—C25—C26	120.1 (3)
C8—C7—C10	106.82 (15)	C24—C25—H25	119.9
C8—C7—C1	109.36 (15)	C26—C25—H25	119.9
C10—C7—C1	111.73 (15)	C21—C26—C25	119.8 (3)
C8—C7—H7	109.6	C21—C26—H26	120.1
C10—C7—H7	109.6	C25—C26—H26	120.1
C1—C7—H7	109.6	C28—C27—C32	118.43 (18)
O1—C8—C9	122.77 (18)	C28—C27—C5	121.58 (17)
O1—C8—C7	119.93 (18)	C32—C27—C5	119.82 (18)
C9—C8—C7	117.30 (17)	C27—C28—C29	120.97 (18)
C8—C9—H9A	109.5	C27—C28—H28	119.5
C8—C9—H9B	109.5	C29—C28—H28	119.5
H9A—C9—H9B	109.5	C30—C29—C28	119.9 (2)
C8—C9—H9C	109.5	C30—C29—H29	120.0
H9A—C9—H9C	109.5	C28—C29—H29	120.0
H9B—C9—H9C	109.5	C31—C30—C29	119.51 (19)
O2—C10—C11	121.19 (17)	C31—C30—H30	120.2
O2—C10—C7	119.91 (17)	C29—C30—H30	120.2
C11—C10—C7	118.70 (16)	C30—C31—C32	120.6 (2)
C12—C11—C16	119.29 (18)	C30—C31—H31	119.7
C12—C11—C10	123.02 (17)	C32—C31—H31	119.7
C16—C11—C10	117.66 (18)	C31—C32—C27	120.5 (2)
C11—C12—C13	119.9 (2)	C31—C32—H32	119.7
C11—C12—H12	120.0	C27—C32—H32	119.7

C6—C1—C2—C18	178.10 (16)	O2—C10—C11—C12	179.81 (19)
C7—C1—C2—C18	−57.3 (2)	C7—C10—C11—C12	4.9 (3)
C6—C1—C2—C17	−64.26 (19)	O2—C10—C11—C16	1.6 (3)
C7—C1—C2—C17	60.3 (2)	C7—C10—C11—C16	−173.24 (18)
C6—C1—C2—C3	58.5 (2)	C16—C11—C12—C13	−0.1 (3)
C7—C1—C2—C3	−176.92 (15)	C10—C11—C12—C13	−178.23 (19)
C18—C2—C3—O3	−63.67 (19)	C11—C12—C13—C14	−0.6 (4)
C17—C2—C3—O3	−179.06 (15)	C12—C13—C14—C15	0.6 (4)
C1—C2—C3—O3	57.22 (19)	C13—C14—C15—C16	−0.1 (4)
C18—C2—C3—C19	56.1 (2)	C14—C15—C16—C11	−0.6 (4)
C17—C2—C3—C19	−59.3 (2)	C12—C11—C16—C15	0.6 (3)
C1—C2—C3—C19	177.02 (17)	C10—C11—C16—C15	178.9 (2)
C18—C2—C3—C4	179.40 (16)	C5—C4—C20—O4	34.1 (2)
C17—C2—C3—C4	64.01 (19)	C3—C4—C20—O4	−87.9 (2)
C1—C2—C3—C4	−59.7 (2)	C5—C4—C20—C21	−150.15 (17)
O3—C3—C4—C20	67.89 (19)	C3—C4—C20—C21	87.8 (2)
C19—C3—C4—C20	−57.1 (2)	O4—C20—C21—C22	−155.3 (2)
C2—C3—C4—C20	−178.56 (15)	C4—C20—C21—C22	29.0 (3)
O3—C3—C4—C5	−54.0 (2)	O4—C20—C21—C26	27.6 (3)
C19—C3—C4—C5	−179.00 (17)	C4—C20—C21—C26	−148.07 (19)
C2—C3—C4—C5	59.5 (2)	C26—C21—C22—C23	0.7 (3)
C20—C4—C5—C27	58.4 (2)	C20—C21—C22—C23	−176.3 (2)
C3—C4—C5—C27	179.24 (15)	C21—C22—C23—C24	1.7 (4)
C20—C4—C5—C6	−179.68 (15)	C22—C23—C24—C25	−1.7 (4)
C3—C4—C5—C6	−58.8 (2)	C23—C24—C25—C26	−0.6 (4)
C7—C1—C6—C5	179.09 (16)	C22—C21—C26—C25	−2.9 (3)
C2—C1—C6—C5	−57.3 (2)	C20—C21—C26—C25	174.2 (2)
C27—C5—C6—C1	−177.85 (16)	C24—C25—C26—C21	2.9 (4)
C4—C5—C6—C1	57.8 (2)	C6—C5—C27—C28	−70.2 (2)
C6—C1—C7—C8	−35.8 (2)	C4—C5—C27—C28	52.3 (2)
C2—C1—C7—C8	−158.06 (16)	C6—C5—C27—C32	105.0 (2)
C6—C1—C7—C10	−153.88 (16)	C4—C5—C27—C32	−132.47 (19)
C2—C1—C7—C10	83.90 (19)	C32—C27—C28—C29	0.0 (3)
C10—C7—C8—O1	−132.18 (18)	C5—C27—C28—C29	175.32 (18)
C1—C7—C8—O1	106.7 (2)	C27—C28—C29—C30	−1.0 (3)
C10—C7—C8—C9	47.5 (2)	C28—C29—C30—C31	1.1 (3)
C1—C7—C8—C9	−73.6 (2)	C29—C30—C31—C32	−0.1 (3)
C8—C7—C10—O2	−91.6 (2)	C30—C31—C32—C27	−0.9 (3)
C1—C7—C10—O2	27.9 (2)	C28—C27—C32—C31	0.9 (3)
C8—C7—C10—C11	83.3 (2)	C5—C27—C32—C31	−174.44 (19)
C1—C7—C10—C11	−157.13 (16)

Hydrogen-bond geometry (Å, º) top

Cg4 is a centroid of the C27–C32 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.94 (3)	1.89 (3)	2.787 (2)	159 (3)
C1—H1···O2	1.00	2.38	2.815 (2)	106
C1—H1···O3	1.00	2.48	2.855 (2)	102
C1—H1···N1ⁱ	1.00	2.50	3.466 (3)	163
C5—H5···O3	1.00	2.53	2.892 (2)	101
C12—H12···O4ⁱⁱ	0.95	2.58	3.242 (3)	127
C28—H28···O2ⁱⁱ	0.95	2.40	3.319 (2)	164
C14—H14···Cg4ⁱⁱⁱ	0.95	2.80	3.475 (2)	129

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

Summary of short interatomic contacts (Å) in the title compound top

Contact	Distance	Symmetry operation
O1···H3	1.89	1 - x, 1/2 + y, 1/2 - z
H9A···H6A	2.39	1 - x, 1 - y, - z
O4···H15	2.73	- 1 + x, y, z
H19B···N1	2.77	1 - x, 1 - y, 1 - z
H26···H31	2.37	x, 1/2 - y, 1/2 + z
C25···C24	3.367	- x, 1 - y, 1 - z
H29···H23	2.41	x, 3/2 - y, - 1/2 + z
H13···H15	2.36	2 - x, 1/2 + y, 1/2 - z

Acknowledgements

This paper has been supported by the Baku State University and the Ministry of Science and Higher Education of the Russian Federation. Authors' contributions are as follows. Conceptualization, ANK and IGM; methodology, ANK and IGM; investigation, ANK, MA and EVD; writing (original draft), MA and ANK; writing (review and editing of the manuscript), MA and ANK; visualization, MA, ANK and IGM; funding acquisition, VNK, FNN and ANK; resources, AAA, VNK and FNN; supervision, ANK and MA.

Funding information

Funding for this research was provided by: Ministry of Science and Higher Education of the Russian Federation (award No. 075-03-2020-223 (FSSF-2020-0017).

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