Crystal structure and Hirshfeld surface analysis of dimethyl 3-methyl-8-{[4-(tri­fluoro­meth­yl)phen­yl]sulfon­yl}-7,8-di­hydro-4H-4,6a-ep­oxy­benzo[b]naphtho­[1,8-de]azepine-5,6-di­carboxyl­ate

Burkin, G.M.; Annadurdyyeva, S.; Kutasevich, A.G.; Guliyeva, N.A.; Hasanov, K.I.; Akkurt, M.; Manahelohe, G.M.

doi:10.1107/S2056989025004426

research communications

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 81| Part 6| June 2025| Pages 543-548

https://doi.org/10.1107/S2056989025004426

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Crystal structure and Hirshfeld surface analysis of dimethyl 3-methyl-8-{[4-(trifluoromethyl)phenyl]sulfonyl}-7,8-dihydro-4H-4,6a-epoxybenzo[b]naphtho[1,8-de]azepine-5,6-dicarboxylate

Gleb M. Burkin,^a Selbi Annadurdyyeva,^a Alexandra G. Kutasevich,^a Narmina A. Guliyeva,^b Khudayar I. Hasanov,^c Mehmet Akkurt ^d and Gizachew Mulugeta Manahelohe ^e ^*

^aRUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation, ^bDepartment of Chemical Engineering, Baku Engineering University, Hasan Aliyev, str. 120, Baku, Absheron AZ0101, Azerbaijan, ^cAzerbaijan Medical University, Scientific Research Centre (SRC), A. Kasumzade St. 14. AZ 1022, Baku, Azerbaijan, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, and ^eDepartment of Chemistry, University of Gondar, PO Box 196, Gondar, Ethiopia
^*Correspondence e-mail: Gizachew.Mulugeta@uog.edu.et

Edited by X. Hao, Institute of Chemistry, Chinese Academy of Sciences (Received 9 May 2025; accepted 16 May 2025; online 23 May 2025)

The molecular conformation of the title compound, C₂₉H₂₂F₃NO₇S, is stable due to the intramolecular C—H⋯O hydrogen bonds. The central seven-membered ring adopts a distorted chair form. In the 7-oxabicyclo[2.2.1]hepta-2,5-diene unit, the five-membered rings adopt envelope conformations. In the crystal, the molecules are linked by C—H⋯O and C—H⋯F interactions, forming sheets parallel to the (002) plane. Additionally, S—O⋯π and π–π interactions [centroid-to-centroid distance = 3.6159 (7) Å] connect the molecules along the a-axis direction. van der Waals interactions between the molecular sheets reinforce the molecular packing. A Hirshfeld surface analysis was conducted to visualize the various intermolecular interactions, indicating that the largest contribution to the surface contacts is from H⋯H interactions (37.3%), followed by O⋯H/H⋯O (24.1%), F⋯H/H⋯F (19.0%), and C⋯H/H⋯C (10.3%) interactions.

Keywords: crystal structure; disorder; acylation; furan; sulfonamide; 4+2 cycloaddition; weak interactions; Hirshfeld surface analysis.

CCDC reference: 2451675

1. Chemical context

7-Oxabicyclo[2.2.1]heptenes, products of the thermic reaction between furans and alkenes or alkynes, have great synthetic potential as a useful tool for the design of a broad diversity of substances with various practical properties. For example, these scaffolds can be used in the synthesis of polycyclic arenes – fragments of graphene – and serve as models for new carbon-based electronic materials (Eda et al., 2015 ; Criado et al., 2013 ; Furrer et al., 2013 ). The 7-oxabicyclo[2.2.1]heptane moiety annelated with other rings serves as a scaffold for the preparation of molecular tweezers (Murphy et al., 2016 ; Warrener et al., 1999 ), supramolecular systems (Chou et al., 2015 ; Oh et al., 2010 ; Eckert-Maksić et al., 2005 ), bridging donor–acceptor molecules (Chakrabarti et al., 2007 ), various bioactive and natural products (Roscalesa et al., 2017 ; Enev et al., 2012 ; Gromov et al., 2009 ; Schindler et al., 2009 ; Vogel et al., 1999 ), high-molecular-weight materials (Margetić et al., 2010 ; Warrener et al., 2001 ; Vogel et al., 1999), etc. Under acid catalysis and temperature, cycloaddition intermediates can be converted into phenols, cyclohexenoles, or substituted aromatic hydrocarbons (Zaytsev et al., 2019 ; Zubkov et al., 2012a ,b ; Guliyeva et al., 2024 ). Continuing our research into the chemistry of furyl-substituted sulfonamides (Burkin et al., 2024 ; Mammadova et al., 2023a ,b ), a new approach toward the cycloaddition of dimethyl but-2-ynedioate (DMAD) with substituted furans (Zubkov et al., 2009 ; Borisova et al., 2018a ,b ) has been developed. In particular, in the course of the thermic [4 + 2] cycloaddition between DMAD and sulfamide 2, an interesting sequence of reaction steps was observed; [4 + 2] cycloaddition, cleavage of the epoxy bridge, and a subsequent aromatization of the cyclohexene ring (Fig. 1).

Figure 1
Synthesis of dimethyl 3-methyl-8-{[4-(trifluoromethyl)phenyl]sulfonyl}-7,8-dihydro-4H-4,6a-epoxybenzo[b]naphtho[1,8-de]azepine-5,6-dicarboxylate.

2. Structural commentary

Fig. 2 shows the molecular structure of the title compound, intramolecular C—H⋯O hydrogen bonds, and naming of the rings in the molecule. The molecular conformation is stable due to the intramolecular hydrogen bonds C7—H7B⋯O17, C7—H7A⋯O1 and C19—H19⋯O2, which form S(6), S(5) and S(5) ring motifs, respectively (Fig. 2; Table 1; Bernstein et al., 1995 ). Fig. 3 shows a detailed view of the central rings of the molecule. The central ring A (C6A/C7/N8/C8A/C12A/C12B/C12C) exhibits a distorted chair form [puckering parameters: q2 = 0.708 (1), q3 = 207 (1) Å, φ(2) = −29.76 (9), φ(3) = −138.1 (4) °, Q_T = 0.738 (1) Å, and spherical polar angle θ(2) = 73.70 (9)°]. Ring A (r.m.s. deviation of fitted atoms = 0.2783 Å) subtends dihedral angles of 20.58 (5), 50.46 (5), 30.64 (5) and 28.18 (5)°, respectively, with rings D (C1–C3/C3A/C12C/C12B), E (C3A/C4–C6/C6A/C12C), F (C8A/C9–C12/C12A) and G (C18–C23). In the 7-oxabicyclo[2.2.1]hepta-2,5-diene unit, the five-membered rings B (O13/C4/C3A/C12C/C6A) and C (O13/C4–C6/C6A) show envelope conformations on atom O13 [B: q(2) = 0.5436 (12) Å, φ(2) = 0.35 (14)° and C: q(2) = 0.5395 (12) Å, φ(2) = 179.95 (14)°]. The bond lengths and angles in the title compound are in good agreement with those reported for related compounds (see Database survey section).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O16ⁱ	1.00	2.49	3.3893 (16)	149
C7—H7A⋯O1	0.99	2.35	2.8481 (15)	111
C7—H7B⋯O17	0.99	2.46	3.0071 (14)	115
C12—H12⋯O2ⁱⁱ	0.95	2.55	3.1357 (15)	120
C15—H15A⋯O13ⁱⁱ	0.98	2.47	3.3741 (17)	153
C17—H17B⋯F1ⁱⁱⁱ	0.98	2.54	3.3033 (17)	135
C19—H19⋯O2	0.95	2.52	2.9003 (17)	104
C22—H22⋯O14ⁱ	0.95	2.37	3.2698 (19)	158
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) ; (iii) .

Figure 2
Molecular structure of the title compound showing atom labelling and ellipsoids at the 30% probability level. The minor disorder component has been omitted for clarity.

Figure 3
A detailed view of the central rings of the title molecule.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal, molecules form R₂²(17) ring motifs by C—H⋯O interactions and are linked by C—H⋯F interactions to form sheets parallel to the (002) plane (Figs. 4 and 5; Table 1). Additionally, S—O⋯π (Fig. 5; Table 1) and π–π interactions [Fig. 6; Cg3⋯Cg6 = 3.6159 (7) Å, slippage = 0.804 Å; where Cg3 and Cg6 are the centroids of rings D (C1–C3/C3A/C12C/C12B) and G (C18–C23), respectively] link the molecules along the a-axis direction. van der Waals interactions between the molecular sheets reinforce the molecular packing.

Figure 4
A view along the a axis of the title compound, showing the crystal packing. C—H⋯O and C—H⋯F hydrogen bonds are shown as dashed lines; H atoms not involved in hydrogen bonding have been omitted.

Figure 5
A view along the b axis of the title compound, showing the crystal packing. C—H⋯O and C—H⋯F hydrogen bonds are shown as dashed lines; H atoms not involved in hydrogen bonding have been omitted.

Figure 6
A partial packing diagram showing S—O⋯π and π–π interactions as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Hirshfeld surfaces and the corresponding two-dimensional fingerprint plots were created using CrystalExplorer17.5 (Spackman et al., 2021 ) in order to visualize the intermolecular interactions (Tables 1 and 2). Fig. 7 shows the full two-dimensional fingerprint plot and those delineated into the major contacts: H⋯H (37.3%), O⋯H/H⋯O (24.1%), F⋯H/H⋯F (19.0%) and C⋯H/H⋯C (10.3%). Smaller contributions are made by O⋯C/C⋯O(4.9%), O⋯O(1.6%), C⋯C (1.5%), F⋯C/C⋯F (0.7%), F⋯O/O⋯F (0.4%), N⋯H/H⋯N (0.2%), S⋯C/C⋯S (0.1%) and S⋯H/H⋯S (0.1%) interactions.

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

Contact	distance	Symmetry operation
F3⋯H17C	2.72	x, −1 + y, z
F1⋯H17B	2.54	−1 + x, −1 + y, z
H12⋯H1	2.54	1 − x, 1 − y, 1 − z
O13⋯H15A	2.47	−1 + x, y, z
O14⋯H22	2.37	1 − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z
O14⋯H15B	2.64	2 − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z
H22⋯O14	2.37	1 − x, − $[{1\over 2}]$ + y, $[{3\over 2}]$ − z
H19⋯H19	2.27	−x, 1 − y, 1 − z
H17A⋯H10	2.51	1 − x, 2 − y, 1 − z
H10⋯H9	2.58	1 − x, 2 − y, 1 − z

Figure 7
(a) The full two-dimensional fingerprint plot for the title compound and those delineated into (b) H⋯H, (c) O⋯H/H⋯O, (c) F⋯H/H⋯F and (c) C⋯H/H⋯C contacts.

4. Database survey

A search of the Cambridge Structural Database (Version 5.41, last update November 2019; Groom et al., 2016 ) for 11-oxatricyclo[6.2.1.0^2,7]undecanes gave 739 hits, while a search for 3-methyl-11-oxatricyclo[6.2.1.0^2,7]undecanes gave zero hits. In these searches, the most related compounds are CSD refcode COKHAP (Sadikhova et al., 2024 ) and POYBEL (Zubkov et al., 2009). In COKHAP, two hexane rings and one oxane ring are fused together. The two hexane rings tend toward a distorted boat conformation, while the tetrahydrofuran and dihydrofuran rings adopt envelope conformations. The oxane ring is puckered. In the crystal, C—H⋯O hydrogen bonds connect the molecules into a three-dimensional network. POYBEL comprises a fused pentacyclic system containing two five-membered (cyclopentane and tetrahydrofuran) and three six-membered (tetrahydropyridinone, tetrahydropyridine and benzene) rings. Both five-membered rings of the bicyclic fragment have the usual envelope conformations, and the two central six-membered rings adopt sofa and non-symmetrical half-chair conformations.

In addition, three related compounds containing the O=S=O group are YIKROD (Mammadova et al., 2023a), KETGID (Schinke et al., 2022 ) and LUJKUA (Yakuth et al., 2024 ). In YIKROD, intramolecular interactions are observed between the furan and benzene rings of the 4-cyanophenyl group. In the crystal, molecules are connected via C—H⋯O and C—H⋯N hydrogen bonds, forming layers parallel to the (100) plane. These layers are interconnected by C⋯H interactions and weak van der Waals interactions. In KETGID, the 1,2-oxazole and methanone fragments form an almost coplanar unit. The crystal structure features three short intermolecular C—H⋯O contacts involving the methanesulfonyl-O atoms. In LUJKUA, the asymmetric unit contains two distinct molecules, which exhibit differences in conformation resulting from a variation in key torsion angles. These distinctions influence the molecular orientation and intermolecular interactions, with strong N—H⋯N and N—H⋯O hydrogen bonds forming a centrosymmetric tetramer stabilized by π–π stacking.

5. Synthesis and crystallization

Dimethyl but-2-ynedioate (133.2 µL, 1.1 mmol) was added to a solution of N-(furan-2-ylmethyl)-N-[2-(5-methylfuran-2-yl)phenyl]-4-(trifluoromethyl)benzenesulfonamide 2 (100 mg, 0.22 mmol) in o-xylene (5 mL). The mixture was refluxed for 5 h. After cooling of the reaction to r.t, the solvent was evaporated under reduced pressure and the crude product was purified by column chromatography (eluent: from hexane to ethyl acetate). The title compound was obtained as colourless powder, yield 27%, 35 mg (0.059 mmol); m.p. 486–487 K. A single crystal of the title compound was grown from ethanol. IR (KBr), ν (cm⁻¹): 1753 (CO₂), 1325 (ν_as SO₂), 1169 (ν_s SO₂). ¹H NMR (700.2 MHz, CDCl₃) (J, Hz): δ 7.71 (dd, J = 7.6, 1.7, 1H, H Ar), 7.50–7.44 (m, 5H, H Ar), 7.20 (d, J = 8.1, 2H, H Ar), 6.69 (d, J = 7.9, 1H, H Ar), 6.61 (d, J = 8.1, 1H, H Ar), 5.91 (s, 1H, H Ar), 5.15 (d, J = 16.7, 1H, NCH), 4.47 (d, J = 16.7, 1H, NCH), 3.76 (s, 3H, OCH₃), 3.47 (s, 3H, OCH₃), 2.29 (s, 3H, CH₃). ¹³C{¹H} NMR (176.1 MHz, CDCl₃): δ there are no signal of CF₃ 163.1, 162.4, 151.2, 150.6, 145.3, 144.1, 142.7, 137.4, 137.0, 133.3 (q, J = 32.4, 1 C), 132.4, 130.9, 130.0, 129.7, 129.2 (2C), 128.3, 127.9 (2C), 126.1, 124.5 (q, J = 4.1, 2 C), 96.9, 81.3, 54.8, 52.5, 52.2, 17.4. ¹⁹F{¹H} NMR (658.8 MHz, CDCl₃): −63.27. MS (ESI) m/z: [M + H]⁺ 586. Elemental analysis calculated (%) for C₂₉H₂₂F₃NO₇S: C 59.49, H 3.79, N 2.39, S 5.48; found: C 59.81, H 3.48, N 2.19, S 5.33.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All C-bound H atoms were positioned geometrically (C—H = 0.95 and 1.00 Å) and refined using a riding model with U_iso(H) = 1.2 or 1.5U_eq(C). The methyl group (C13) attached to the benzene ring was found to be disordered over two positions with a refined occupancy ratio of 0.53 (2): 0.47 (2). A SADI instruction was used to restrain the C3—C13 and C3—C13′ bonds. The anisotropic displacement parameters of both parts of the carbon atom of the disordered methyl group were restrained to be similar with EADP instruction.

Table 3
Experimental details

Crystal data
Chemical formula	C₂₉H₂₂F₃NO₇S
M_r	585.53
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.6375 (5), 11.0324 (6), 30.2019 (8)
β (°)	93.983 (1)
V (Å³)	2538.7 (2)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.79
Crystal size (mm)	0.35 × 0.18 × 0.17

Data collection
Diffractometer	Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.713, 0.737
No. of measured, independent and observed [I > 2σ(I)] reflections	31570, 5526, 5187
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.103, 1.05
No. of reflections	5526
No. of parameters	379
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.43
Computer programs: CrysAlis PRO (Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2016/6 (Sheldrick, 2015a ), SHELXL2016/6 (Sheldrick, 2015b , ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2451675

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989025004426/nx2026sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025004426/nx2026Isup2.hkl

checkCIF report

Computing details top

Dimethyl 3-methyl-8-{[4-(trifluoromethyl)phenyl]sulfonyl}-7,8-dihydro-4H-4,6a-epoxybenzo[b]naphtho[1,8-de]azepine-5,6-dicarboxylate top

Crystal data top

C₂₉H₂₂F₃NO₇S	F(000) = 1208
M_r = 585.53	D_x = 1.532 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 7.6375 (5) Å	Cell parameters from 20964 reflections
b = 11.0324 (6) Å	θ = 2.9–79.9°
c = 30.2019 (8) Å	µ = 1.79 mm⁻¹
β = 93.983 (1)°	T = 100 K
V = 2538.7 (2) Å³	Prism, colourless
Z = 4	0.35 × 0.18 × 0.17 mm

Data collection top

Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector diffractometer	5187 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.049
φ and ω scans	θ_max = 80.1°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −9→8
T_min = 0.713, T_max = 0.737	k = −14→13
31570 measured reflections	l = −38→38
5526 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0633P)² + 0.8141P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
5526 reflections	Δρ_max = 0.45 e Å⁻³
379 parameters	Δρ_min = −0.43 e Å⁻³
1 restraint	Extinction correction: SHELXL-2019/2 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: difference Fourier map	Extinction coefficient: 0.00089 (14)

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	Occ. (<1)
S1	−0.08268 (3)	0.68046 (3)	0.60331 (2)	0.01536 (10)
F1	0.03672 (12)	0.08285 (8)	0.60261 (3)	0.0324 (2)
F2	0.22478 (16)	0.13678 (9)	0.55695 (5)	0.0501 (3)
F3	0.29014 (14)	0.14333 (10)	0.62756 (5)	0.0539 (3)
O1	−0.16062 (12)	0.70213 (9)	0.64434 (3)	0.0216 (2)
O2	−0.17402 (12)	0.70996 (9)	0.56162 (3)	0.0225 (2)
C1	0.48862 (15)	0.49339 (11)	0.57852 (4)	0.0171 (2)
H1	0.496038	0.479440	0.547665	0.021*
C2	0.55556 (16)	0.40746 (11)	0.60859 (4)	0.0187 (2)
H2	0.607100	0.336071	0.597644	0.022*
C3	0.54990 (15)	0.42217 (11)	0.65483 (4)	0.0172 (2)
C3A	0.47063 (15)	0.52723 (11)	0.66816 (4)	0.0156 (2)
C4	0.44151 (15)	0.58212 (12)	0.71373 (4)	0.0171 (2)
H4	0.444763	0.524274	0.739264	0.021*
C5	0.56803 (16)	0.69088 (11)	0.71852 (4)	0.0165 (2)
C6	0.50225 (15)	0.77414 (11)	0.68956 (4)	0.0149 (2)
C6A	0.33411 (15)	0.71572 (11)	0.66698 (4)	0.0141 (2)
C7	0.18668 (15)	0.79745 (11)	0.64834 (4)	0.0158 (2)
H7A	0.096592	0.803245	0.670287	0.019*
H7B	0.234316	0.879823	0.644221	0.019*
N8	0.10246 (13)	0.75554 (9)	0.60592 (3)	0.0148 (2)
C8A	0.19749 (15)	0.76703 (11)	0.56657 (4)	0.0144 (2)
C9	0.14221 (16)	0.85518 (12)	0.53567 (4)	0.0186 (2)
H9	0.041411	0.902688	0.540357	0.022*
C10	0.23335 (17)	0.87407 (12)	0.49810 (4)	0.0217 (3)
H10	0.195141	0.934034	0.477015	0.026*
C11	0.38118 (17)	0.80441 (12)	0.49158 (4)	0.0202 (3)
H11	0.445235	0.817581	0.466155	0.024*
C12	0.43538 (16)	0.71573 (12)	0.52212 (4)	0.0171 (2)
H12	0.535760	0.668175	0.517074	0.020*
C12A	0.34499 (15)	0.69485 (11)	0.56029 (4)	0.0143 (2)
C12B	0.40963 (14)	0.60123 (11)	0.59260 (4)	0.0144 (2)
C12C	0.40171 (14)	0.61400 (11)	0.63793 (4)	0.0137 (2)
O13	0.27786 (11)	0.64524 (8)	0.70381 (3)	0.01706 (19)
C13	0.6235 (19)	0.3275 (12)	0.6870 (4)	0.0238 (3)	0.53 (2)
H13A	0.732679	0.294903	0.676576	0.036*	0.53 (2)
H13B	0.538176	0.261703	0.689067	0.036*	0.53 (2)
H13C	0.647483	0.364271	0.716356	0.036*	0.53 (2)
C13'	0.625 (2)	0.3275 (13)	0.6867 (5)	0.0238 (3)	0.47 (2)
H13D	0.747394	0.348027	0.695799	0.036*	0.47 (2)
H13E	0.621140	0.248114	0.672104	0.036*	0.47 (2)
H13F	0.556513	0.324858	0.712874	0.036*	0.47 (2)
C14	0.74252 (17)	0.68539 (12)	0.74318 (4)	0.0187 (3)
O14	0.82551 (14)	0.77048 (10)	0.75805 (4)	0.0298 (2)
O15	0.79316 (12)	0.56938 (9)	0.74709 (3)	0.0221 (2)
C15	0.96586 (17)	0.54877 (14)	0.76935 (5)	0.0252 (3)
H15A	1.051895	0.601521	0.756353	0.038*
H15B	0.999568	0.463854	0.765660	0.038*
H15C	0.962354	0.567077	0.801032	0.038*
C16	0.58807 (15)	0.88141 (11)	0.67119 (4)	0.0160 (2)
O16	0.68066 (13)	0.95432 (9)	0.69113 (3)	0.0247 (2)
O17	0.54422 (11)	0.88538 (8)	0.62730 (3)	0.01773 (19)
C17	0.63324 (19)	0.97498 (13)	0.60257 (5)	0.0244 (3)
H17A	0.585829	0.974193	0.571579	0.037*
H17B	0.759006	0.956514	0.603902	0.037*
H17C	0.615553	1.055289	0.615390	0.037*
C18	−0.02522 (15)	0.52580 (11)	0.60113 (4)	0.0161 (2)
C19	−0.01841 (17)	0.47033 (12)	0.56005 (4)	0.0213 (3)
H19	−0.055255	0.512804	0.533666	0.026*
C20	0.04285 (18)	0.35202 (13)	0.55788 (5)	0.0241 (3)
H20	0.049166	0.312688	0.530058	0.029*
C21	0.09484 (17)	0.29210 (12)	0.59721 (5)	0.0220 (3)
C22	0.08252 (17)	0.34703 (12)	0.63835 (5)	0.0224 (3)
H22	0.115329	0.303757	0.664827	0.027*
C23	0.02216 (17)	0.46516 (12)	0.64049 (4)	0.0195 (3)
H23	0.013327	0.503979	0.668321	0.023*
C24	0.16202 (19)	0.16488 (13)	0.59579 (6)	0.0296 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01088 (15)	0.01765 (16)	0.01767 (16)	0.00027 (9)	0.00183 (11)	0.00049 (10)
F1	0.0335 (5)	0.0180 (4)	0.0464 (5)	−0.0065 (3)	0.0085 (4)	−0.0001 (4)
F2	0.0591 (7)	0.0245 (5)	0.0717 (8)	0.0035 (4)	0.0407 (6)	−0.0050 (5)
F3	0.0374 (5)	0.0263 (5)	0.0941 (10)	0.0095 (4)	−0.0236 (6)	−0.0078 (5)
O1	0.0165 (4)	0.0240 (5)	0.0252 (5)	0.0012 (3)	0.0086 (4)	−0.0018 (4)
O2	0.0159 (4)	0.0257 (5)	0.0250 (5)	−0.0014 (3)	−0.0049 (3)	0.0034 (4)
C1	0.0160 (5)	0.0185 (6)	0.0170 (5)	−0.0007 (4)	0.0020 (4)	−0.0035 (4)
C2	0.0174 (5)	0.0157 (5)	0.0231 (6)	0.0007 (4)	0.0027 (4)	−0.0026 (4)
C3	0.0137 (5)	0.0166 (6)	0.0213 (6)	−0.0015 (4)	0.0013 (4)	0.0031 (4)
C3A	0.0129 (5)	0.0186 (6)	0.0154 (5)	−0.0025 (4)	0.0017 (4)	0.0016 (4)
C4	0.0153 (5)	0.0215 (6)	0.0148 (5)	0.0005 (4)	0.0025 (4)	0.0028 (4)
C5	0.0169 (6)	0.0218 (6)	0.0110 (5)	0.0010 (4)	0.0028 (4)	−0.0018 (4)
C6	0.0143 (5)	0.0193 (6)	0.0114 (5)	0.0005 (4)	0.0023 (4)	−0.0036 (4)
C6A	0.0137 (5)	0.0174 (5)	0.0116 (5)	−0.0014 (4)	0.0035 (4)	0.0002 (4)
C7	0.0142 (5)	0.0178 (5)	0.0155 (5)	0.0011 (4)	0.0013 (4)	−0.0029 (4)
N8	0.0123 (4)	0.0175 (5)	0.0144 (5)	−0.0002 (4)	0.0012 (4)	−0.0006 (4)
C8A	0.0133 (5)	0.0157 (5)	0.0141 (5)	−0.0026 (4)	0.0011 (4)	−0.0011 (4)
C9	0.0182 (5)	0.0183 (6)	0.0192 (6)	0.0011 (4)	0.0003 (4)	0.0015 (5)
C10	0.0244 (6)	0.0218 (6)	0.0188 (6)	−0.0007 (5)	0.0002 (5)	0.0054 (5)
C11	0.0210 (6)	0.0258 (6)	0.0141 (5)	−0.0032 (5)	0.0033 (4)	0.0017 (5)
C12	0.0150 (5)	0.0217 (6)	0.0146 (5)	−0.0011 (4)	0.0011 (4)	−0.0027 (4)
C12A	0.0139 (5)	0.0161 (5)	0.0128 (5)	−0.0021 (4)	−0.0010 (4)	−0.0022 (4)
C12B	0.0117 (5)	0.0165 (5)	0.0151 (5)	−0.0014 (4)	0.0012 (4)	−0.0010 (4)
C12C	0.0108 (5)	0.0148 (5)	0.0155 (5)	−0.0007 (4)	0.0018 (4)	−0.0009 (4)
O13	0.0149 (4)	0.0225 (4)	0.0142 (4)	0.0008 (3)	0.0043 (3)	0.0036 (3)
C13	0.0248 (7)	0.0199 (6)	0.0267 (7)	0.0026 (5)	0.0027 (6)	0.0074 (5)
C13'	0.0248 (7)	0.0199 (6)	0.0267 (7)	0.0026 (5)	0.0027 (6)	0.0074 (5)
C14	0.0192 (6)	0.0258 (6)	0.0112 (5)	0.0013 (5)	0.0007 (4)	0.0012 (4)
O14	0.0306 (5)	0.0287 (5)	0.0282 (5)	−0.0025 (4)	−0.0117 (4)	−0.0016 (4)
O15	0.0185 (4)	0.0259 (5)	0.0216 (4)	0.0025 (4)	−0.0020 (3)	0.0031 (4)
C15	0.0177 (6)	0.0360 (7)	0.0217 (6)	0.0042 (5)	−0.0010 (5)	0.0066 (5)
C16	0.0151 (5)	0.0168 (5)	0.0164 (5)	0.0021 (4)	0.0024 (4)	−0.0020 (4)
O16	0.0266 (5)	0.0233 (5)	0.0236 (5)	−0.0069 (4)	−0.0016 (4)	−0.0053 (4)
O17	0.0190 (4)	0.0192 (4)	0.0150 (4)	−0.0035 (3)	0.0011 (3)	0.0015 (3)
C17	0.0274 (6)	0.0215 (6)	0.0246 (6)	−0.0037 (5)	0.0051 (5)	0.0066 (5)
C18	0.0127 (5)	0.0180 (6)	0.0179 (6)	−0.0022 (4)	0.0028 (4)	−0.0001 (4)
C19	0.0243 (6)	0.0231 (6)	0.0167 (6)	−0.0038 (5)	0.0035 (5)	−0.0010 (5)
C20	0.0276 (7)	0.0220 (6)	0.0235 (6)	−0.0045 (5)	0.0069 (5)	−0.0050 (5)
C21	0.0169 (6)	0.0171 (6)	0.0325 (7)	−0.0035 (5)	0.0045 (5)	−0.0018 (5)
C22	0.0218 (6)	0.0198 (6)	0.0250 (6)	−0.0031 (5)	−0.0016 (5)	0.0030 (5)
C23	0.0210 (6)	0.0199 (6)	0.0175 (6)	−0.0025 (5)	0.0010 (4)	−0.0003 (4)
C24	0.0227 (7)	0.0199 (6)	0.0469 (9)	−0.0026 (5)	0.0067 (6)	−0.0021 (6)

Geometric parameters (Å, º) top

S1—O1	1.4314 (9)	C10—H10	0.9500
S1—O2	1.4338 (10)	C11—C12	1.3877 (18)
S1—N8	1.6359 (10)	C11—H11	0.9500
S1—C18	1.7642 (13)	C12—C12A	1.4034 (16)
F1—C24	1.3434 (17)	C12—H12	0.9500
F2—C24	1.334 (2)	C12A—C12B	1.4819 (17)
F3—C24	1.343 (2)	C12B—C12C	1.3816 (16)
C1—C2	1.3857 (18)	C13—H13A	0.9800
C1—C12B	1.4129 (17)	C13—H13B	0.9800
C1—H1	0.9500	C13—H13C	0.9800
C2—C3	1.4096 (18)	C13'—H13D	0.9800
C2—H2	0.9500	C13'—H13E	0.9800
C3—C3A	1.3805 (17)	C13'—H13F	0.9800
C3—C13'	1.507 (10)	C14—O14	1.2022 (18)
C3—C13	1.509 (9)	C14—O15	1.3400 (17)
C3A—C12C	1.4001 (17)	O15—C15	1.4562 (15)
C3A—C4	1.5340 (17)	C15—H15A	0.9800
C4—O13	1.4439 (15)	C15—H15B	0.9800
C4—C5	1.5411 (17)	C15—H15C	0.9800
C4—H4	1.0000	C16—O16	1.2045 (16)
C5—C6	1.3416 (18)	C16—O17	1.3452 (15)
C5—C14	1.4820 (17)	O17—C17	1.4378 (15)
C6—C16	1.4795 (17)	C17—H17A	0.9800
C6—C6A	1.5517 (16)	C17—H17B	0.9800
C6A—O13	1.4466 (13)	C17—H17C	0.9800
C6A—C7	1.5198 (16)	C18—C19	1.3876 (17)
C6A—C12C	1.5358 (16)	C18—C23	1.3899 (18)
C7—N8	1.4680 (15)	C19—C20	1.390 (2)
C7—H7A	0.9900	C19—H19	0.9500
C7—H7B	0.9900	C20—C21	1.393 (2)
N8—C8A	1.4405 (15)	C20—H20	0.9500
C8A—C9	1.3928 (17)	C21—C22	1.391 (2)
C8A—C12A	1.4031 (17)	C21—C24	1.4961 (19)
C9—C10	1.3877 (18)	C22—C23	1.3854 (19)
C9—H9	0.9500	C22—H22	0.9500
C10—C11	1.3910 (19)	C23—H23	0.9500

O1—S1—O2	121.06 (6)	C12—C12A—C12B	119.67 (11)
O1—S1—N8	106.49 (6)	C12C—C12B—C1	115.67 (11)
O2—S1—N8	107.06 (5)	C12C—C12B—C12A	123.09 (11)
O1—S1—C18	108.27 (6)	C1—C12B—C12A	121.22 (11)
O2—S1—C18	107.08 (6)	C12B—C12C—C3A	122.41 (11)
N8—S1—C18	105.97 (5)	C12B—C12C—C6A	132.85 (11)
C2—C1—C12B	121.64 (11)	C3A—C12C—C6A	104.66 (10)
C2—C1—H1	119.2	C4—O13—C6A	96.88 (8)
C12B—C1—H1	119.2	C3—C13—H13A	109.5
C1—C2—C3	122.36 (11)	C3—C13—H13B	109.5
C1—C2—H2	118.8	H13A—C13—H13B	109.5
C3—C2—H2	118.8	C3—C13—H13C	109.5
C3A—C3—C2	115.46 (11)	H13A—C13—H13C	109.5
C3A—C3—C13'	123.5 (7)	H13B—C13—H13C	109.5
C2—C3—C13'	121.1 (7)	C3—C13'—H13D	109.5
C3A—C3—C13	123.0 (6)	C3—C13'—H13E	109.5
C2—C3—C13	121.5 (6)	H13D—C13'—H13E	109.5
C3—C3A—C12C	122.45 (11)	C3—C13'—H13F	109.5
C3—C3A—C4	133.39 (11)	H13D—C13'—H13F	109.5
C12C—C3A—C4	104.11 (10)	H13E—C13'—H13F	109.5
O13—C4—C3A	100.46 (9)	O14—C14—O15	124.85 (12)
O13—C4—C5	99.91 (10)	O14—C14—C5	126.04 (12)
C3A—C4—C5	105.22 (9)	O15—C14—C5	109.10 (11)
O13—C4—H4	116.3	C14—O15—C15	115.88 (11)
C3A—C4—H4	116.3	O15—C15—H15A	109.5
C5—C4—H4	116.3	O15—C15—H15B	109.5
C6—C5—C14	129.68 (12)	H15A—C15—H15B	109.5
C6—C5—C4	105.54 (11)	O15—C15—H15C	109.5
C14—C5—C4	123.47 (11)	H15A—C15—H15C	109.5
C5—C6—C16	129.54 (11)	H15B—C15—H15C	109.5
C5—C6—C6A	105.26 (10)	O16—C16—O17	124.64 (12)
C16—C6—C6A	122.82 (10)	O16—C16—C6	127.35 (12)
O13—C6A—C7	110.59 (9)	O17—C16—C6	108.01 (10)
O13—C6A—C12C	100.14 (9)	C16—O17—C17	116.09 (10)
C7—C6A—C12C	119.46 (10)	O17—C17—H17A	109.5
O13—C6A—C6	99.57 (9)	O17—C17—H17B	109.5
C7—C6A—C6	119.05 (10)	H17A—C17—H17B	109.5
C12C—C6A—C6	104.71 (9)	O17—C17—H17C	109.5
N8—C7—C6A	113.89 (10)	H17A—C17—H17C	109.5
N8—C7—H7A	108.8	H17B—C17—H17C	109.5
C6A—C7—H7A	108.8	C19—C18—C23	121.92 (12)
N8—C7—H7B	108.8	C19—C18—S1	119.01 (10)
C6A—C7—H7B	108.8	C23—C18—S1	118.95 (10)
H7A—C7—H7B	107.7	C18—C19—C20	119.34 (12)
C8A—N8—C7	118.49 (9)	C18—C19—H19	120.3
C8A—N8—S1	119.23 (8)	C20—C19—H19	120.3
C7—N8—S1	121.75 (8)	C19—C20—C21	118.86 (12)
C9—C8A—C12A	120.98 (11)	C19—C20—H20	120.6
C9—C8A—N8	117.87 (11)	C21—C20—H20	120.6
C12A—C8A—N8	121.12 (10)	C22—C21—C20	121.45 (13)
C10—C9—C8A	120.45 (12)	C22—C21—C24	118.61 (13)
C10—C9—H9	119.8	C20—C21—C24	119.93 (13)
C8A—C9—H9	119.8	C23—C22—C21	119.65 (12)
C9—C10—C11	119.40 (12)	C23—C22—H22	120.2
C9—C10—H10	120.3	C21—C22—H22	120.2
C11—C10—H10	120.3	C22—C23—C18	118.72 (12)
C12—C11—C10	120.20 (12)	C22—C23—H23	120.6
C12—C11—H11	119.9	C18—C23—H23	120.6
C10—C11—H11	119.9	F2—C24—F3	107.37 (13)
C11—C12—C12A	121.37 (11)	F2—C24—F1	106.36 (13)
C11—C12—H12	119.3	F3—C24—F1	105.22 (13)
C12A—C12—H12	119.3	F2—C24—C21	112.84 (13)
C8A—C12A—C12	117.59 (11)	F3—C24—C21	112.32 (13)
C8A—C12A—C12B	122.72 (10)	F1—C24—C21	112.23 (11)

C12B—C1—C2—C3	−0.27 (19)	C12—C12A—C12B—C12C	143.46 (12)
C1—C2—C3—C3A	0.97 (18)	C8A—C12A—C12B—C1	146.80 (12)
C1—C2—C3—C13'	−179.4 (8)	C12—C12A—C12B—C1	−34.76 (17)
C1—C2—C3—C13	180.0 (7)	C1—C12B—C12C—C3A	1.32 (17)
C2—C3—C3A—C12C	−0.53 (17)	C12A—C12B—C12C—C3A	−176.99 (11)
C13'—C3—C3A—C12C	179.9 (8)	C1—C12B—C12C—C6A	177.79 (11)
C13—C3—C3A—C12C	−179.5 (7)	C12A—C12B—C12C—C6A	−0.5 (2)
C2—C3—C3A—C4	−177.38 (12)	C3—C3A—C12C—C12B	−0.65 (18)
C13'—C3—C3A—C4	3.0 (8)	C4—C3A—C12C—C12B	177.00 (11)
C13—C3—C3A—C4	3.6 (7)	C3—C3A—C12C—C6A	−177.97 (11)
C3—C3A—C4—O13	−148.68 (13)	C4—C3A—C12C—C6A	−0.32 (11)
C12C—C3A—C4—O13	34.06 (11)	O13—C6A—C12C—C12B	149.70 (12)
C3—C3A—C4—C5	107.93 (15)	C7—C6A—C12C—C12B	28.95 (18)
C12C—C3A—C4—C5	−69.34 (11)	C6—C6A—C12C—C12B	−107.51 (14)
O13—C4—C5—C6	−33.53 (11)	O13—C6A—C12C—C3A	−33.39 (11)
C3A—C4—C5—C6	70.27 (12)	C7—C6A—C12C—C3A	−154.14 (10)
O13—C4—C5—C14	158.45 (10)	C6—C6A—C12C—C3A	69.41 (11)
C3A—C4—C5—C14	−97.75 (13)	C3A—C4—O13—C6A	−54.37 (10)
C14—C5—C6—C16	4.6 (2)	C5—C4—O13—C6A	53.28 (10)
C4—C5—C6—C16	−162.42 (11)	C7—C6A—O13—C4	−179.14 (10)
C14—C5—C6—C6A	167.07 (12)	C12C—C6A—O13—C4	53.93 (10)
C4—C5—C6—C6A	0.07 (12)	C6—C6A—O13—C4	−53.03 (10)
C5—C6—C6A—O13	33.30 (11)	C6—C5—C14—O14	36.1 (2)
C16—C6—C6A—O13	−162.73 (10)	C4—C5—C14—O14	−158.94 (13)
C5—C6—C6A—C7	153.40 (10)	C6—C5—C14—O15	−144.93 (13)
C16—C6—C6A—C7	−42.62 (15)	C4—C5—C14—O15	20.01 (16)
C5—C6—C6A—C12C	−69.93 (11)	O14—C14—O15—C15	−3.06 (18)
C16—C6—C6A—C12C	94.05 (12)	C5—C14—O15—C15	177.98 (10)
O13—C6A—C7—N8	−105.16 (11)	C5—C6—C16—O16	−44.8 (2)
C12C—C6A—C7—N8	10.18 (15)	C6A—C6—C16—O16	155.42 (12)
C6—C6A—C7—N8	140.52 (10)	C5—C6—C16—O17	135.61 (13)
C6A—C7—N8—C8A	−72.75 (13)	C6A—C6—C16—O17	−24.19 (14)
C6A—C7—N8—S1	98.88 (11)	O16—C16—O17—C17	8.00 (17)
O1—S1—N8—C8A	−170.14 (9)	C6—C16—O17—C17	−172.38 (10)
O2—S1—N8—C8A	−39.32 (10)	O1—S1—C18—C19	152.89 (10)
C18—S1—N8—C8A	74.73 (10)	O2—S1—C18—C19	20.83 (11)
O1—S1—N8—C7	18.29 (11)	N8—S1—C18—C19	−93.20 (11)
O2—S1—N8—C7	149.11 (9)	O1—S1—C18—C23	−30.97 (11)
C18—S1—N8—C7	−96.85 (10)	O2—S1—C18—C23	−163.03 (10)
C7—N8—C8A—C9	−107.68 (13)	N8—S1—C18—C23	82.94 (11)
S1—N8—C8A—C9	80.47 (13)	C23—C18—C19—C20	−2.14 (19)
C7—N8—C8A—C12A	70.01 (15)	S1—C18—C19—C20	173.88 (10)
S1—N8—C8A—C12A	−101.83 (12)	C18—C19—C20—C21	0.4 (2)
C12A—C8A—C9—C10	−0.56 (19)	C19—C20—C21—C22	1.6 (2)
N8—C8A—C9—C10	177.14 (11)	C19—C20—C21—C24	−179.74 (12)
C8A—C9—C10—C11	−0.2 (2)	C20—C21—C22—C23	−1.9 (2)
C9—C10—C11—C12	0.9 (2)	C24—C21—C22—C23	179.43 (12)
C10—C11—C12—C12A	−0.7 (2)	C21—C22—C23—C18	0.18 (19)
C9—C8A—C12A—C12	0.70 (17)	C19—C18—C23—C22	1.85 (19)
N8—C8A—C12A—C12	−176.93 (10)	S1—C18—C23—C22	−174.17 (9)
C9—C8A—C12A—C12B	179.17 (11)	C22—C21—C24—F2	−158.19 (13)
N8—C8A—C12A—C12B	1.54 (17)	C20—C21—C24—F2	23.13 (19)
C11—C12—C12A—C8A	−0.05 (18)	C22—C21—C24—F3	−36.65 (18)
C11—C12—C12A—C12B	−178.57 (11)	C20—C21—C24—F3	144.67 (14)
C2—C1—C12B—C12C	−0.87 (17)	C22—C21—C24—F1	81.66 (17)
C2—C1—C12B—C12A	177.47 (11)	C20—C21—C24—F1	−97.02 (16)
C8A—C12A—C12B—C12C	−34.98 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O16ⁱ	1.00	2.49	3.3893 (16)	149
C7—H7A···O1	0.99	2.35	2.8481 (15)	111
C7—H7B···O17	0.99	2.46	3.0071 (14)	115
C12—H12···O2ⁱⁱ	0.95	2.55	3.1357 (15)	120
C15—H15A···O13ⁱⁱ	0.98	2.47	3.3741 (17)	153
C17—H17B···F1ⁱⁱⁱ	0.98	2.54	3.3033 (17)	135
C19—H19···O2	0.95	2.52	2.9003 (17)	104
C22—H22···O14ⁱ	0.95	2.37	3.2698 (19)	158

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

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

Contact	distance	Symmetry operation
F3···H17C	2.72	x, -1 + y, z
F1···H17B	2.54	-1 + x, -1 + y, z
H12···H1	2.54	1 - x, 1 - y, 1 - z
O13···H15A	2.47	-1 + x, y, z
O14···H22	2.37	1 - x, 1/2 + y, 3/2 - z
O14···H15B	2.64	2 - x, 1/2 + y, 3/2 - z
H22···O14	2.37	1 - x, -1/2 + y, 3/2 - z
H19···H19	2.27	-x, 1 - y, 1 - z
H17A···H10	2.51	1 - x, 2 - y, 1 - z
H10···H9	2.58	1 - x, 2 - y, 1 - z

Acknowledgements

GMB and SA thank to Common Use Center `Physical and Chemical Research of New Materials, Substances and Catalytic Systems'. This publication has been supported by the RUDN University Scientific Projects Grant System, project No. 021408–2-000, as well as by the Baku Engineering University (Azerbaijan) and Azerbaijan Medical University. The author's contributions are as follows. Conceptualization, MA and GMM; synthesis, GMB and SA; AGK NMR analysis; X-ray analysis, VNK, NAG; writing (review and editing of the manuscript) MA and GMM; funding acquisition KIH; supervision, MA and GMM.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Borisova, K., Nikitina, E., Novikov, R., Khrustalev, V., Dorovatovskii, P., Zubavichus, Y., Kuznetsov, M., Zaytsev, V., Varlamov, A. & Zubkov, F. (2018a). Chem. Commun. 54, 2850–2853. Web of Science CSD CrossRef CAS Google Scholar
Borisova, K. K., Kvyatkovskaya, E. A., Nikitina, E. V., Aysin, R. R., Novikov, R. A. & Zubkov, F. I. (2018b). J. Org. Chem. 83, 4840–4850. Web of Science CSD CrossRef CAS PubMed Google Scholar
Burkin, G. M., Kvyatkovskaya, E. A., Khrustalev, V. N., Hasanov, K. I., Sadikhova, N. D., Akkurt, M. & Bhattarai, A. (2024). Acta Cryst. E80, 418–422. CSD CrossRef IUCr Journals Google Scholar
Chakrabarti, S., Liu, M., Waldeck, D. H., Oliver, A. M. & Paddon-Row, M. N. (2007). J. Am. Chem. Soc. 129, 3247–3256. CrossRef PubMed CAS Google Scholar
Chou, T.-C. & Li, Y.-J. (2015). Tetrahedron 71, 5620–5633. CSD CrossRef CAS Google Scholar
Criado, A., Vilas-Varela, M., Cobas, A., Peréz, D., Pena, D. & Guitián, E. (2013). J. Org. Chem. 78, 12637–12649. CSD CrossRef CAS PubMed Google Scholar
Eckert-Maksić, M., Margetić, D., Kirin, S., Milić, D. & Matković-Čalogović, D. (2005). Eur. J. Org. Chem. pp. 4612–4620. Google Scholar
Eda, S., Eguchi, F., Haneda, H. & Hamura, T. (2015). Chem. Commun. 51, 5963–5966. Web of Science CSD CrossRef CAS Google Scholar
Enev, V. S., Felzmann, W., Gromov, A., Marchart, S. & Mulzer, J. (2012). Chem. Eur. J. 18, 9651–9668. CrossRef CAS PubMed Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Furrer, F., Linden, A. & Stuparu, M. C. (2013). Chem. Eur. J. 19, 13199–13206. CSD CrossRef CAS PubMed Google Scholar
Gromov, A., Enev, V. & Mulzer, J. (2009). Org. Lett. 11, 2884–2886. CSD CrossRef PubMed CAS Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Guliyeva, N. A., Burkin, G. M., Annadurdyyeva, S., Khrustalev, V. N., Atioğlu, Z., Akkurt, M. & Bhattarai, A. (2024). Acta Cryst. E80, 62–66. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mammadova, G. Z., Annadurdyyeva, S., Burkin, G. M., Khrustalev, V. N., Akkurt, M., Yıldırım, S. Ö. & Bhattarai, A. (2023b). Acta Cryst. E79, 499–503. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mammadova, G. Z., Yakovleva, E. D., Burkin, G. M., Khrustalev, V. N., Akkurt, M., Çelikesir, S. T. & Bhattarai, A. (2023a). Acta Cryst. E79, 747–751. Web of Science CSD CrossRef IUCr Journals Google Scholar
Margetić, D., Eckert-Maksić, M., Trošelj, P. & Marinić, Z. (2010). J. Fluorine Chem. 131, 408–416. Google Scholar
Murphy, R. B., Norman, R. E., White, J. M., Perkins, M. V. & Johnston, M. R. (2016). Org. Biomol. Chem. 14, 8707–8720. Web of Science CSD CrossRef CAS PubMed Google Scholar
Oh, C. H., Yi, H. J. & Lee, K. H. (2010). Bull. Korean Chem. Soc. 31, 683–688. Web of Science CrossRef CAS Google Scholar
Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Roscalesa, S. & Plumet, J. (2017). Nat. Prod. Commun. 12, 713–732. PubMed Google Scholar
Sadikhova, N. D., Atioğlu, Z., Guliyeva, N. A., Podrezova, A. G., Nikitina, E. V., Akkurt, M. & Bhattarai, A. (2024). Acta Cryst. E80, 83–87. CSD CrossRef IUCr Journals Google Scholar
Schindler, C. S. & Carreira, E. M. (2009). Chem. Soc. Rev. 38, 3222–3241. CrossRef PubMed CAS Google Scholar
Schinke, J., Gelbrich, T. & Griesser, U. J. (2022). Acta Cryst. E78, 979–983. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst. 54, 1006–1011. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Vinaya, Yakuth, S. A., Mohan Kumar, T. M., Bhaskar, B. L., Divakara, T. R., Yathirajan, H. S., Basavaraju, Y. B. & Parkin, S. (2024). Acta Cryst. E80, 1354–1358. CSD CrossRef IUCr Journals Google Scholar
Vogel, P., Cossy, J., Plumet, J. & Arjona, O. (1999). Tetrahedron 55, 13521–13642. CrossRef CAS Google Scholar
Warrener, R. N., Margetic, D., Amarasekara, A. S., Butler, D. N., Mahadevan, I. B. & Russell, R. A. (1999). Org. Lett. 1, 199–202. Web of Science CrossRef CAS Google Scholar
Warrener, R. N., Margetić, D., Foley, P. J., Butler, D. N., Winling, A., Beales, K. A. & Russell, R. A. (2001). Tetrahedron 57, 571–582. CrossRef CAS Google Scholar
Zaytsev, V. P., Mertsalov, D. F., Chervyakova, L. V., Krishna, G., Zubkov, F. I., Dorovatovskii, P. V., Khrustalev, V. N. & Zarubaev, V. V. (2019). Tetrahedron Lett. 60, 151204. Web of Science CSD CrossRef Google Scholar
Zubkov, F. I., Airiyan, I. K., Ershova, J. D., Galeev, T. R., Zaytsev, V. P., Nikitina, E. V. & Varlamov, A. V. (2012b). RSC Adv. 2, 4103–4109. Web of Science CrossRef CAS Google Scholar
Zubkov, F. I., Ershova, J. D., Orlova, A. A., Zaytsev, V. P., Nikitina, E. V., Peregudov, A. S., Gurbanov, A. V., Borisov, R. S., Khrustalev, V. N., Maharramov, A. M. & Varlamov, A. V. (2009). Tetrahedron 65, 3789–3803. CSD CrossRef CAS Google Scholar
Zubkov, F. I., Zaytsev, V. P., Puzikova, E. S., Nikitina, E. V., Khrustalev, V. N., Novikov, R. A. & Varlamov, A. V. (2012a). Chem. Heterocycl. Compd. 48, 514–524. CrossRef CAS Google Scholar

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