research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 82| Part 2| February 2026| Pages 126-131
https://doi.org/10.1107/S2056989025011582

Synthesis, crystal structure and Hirshfeld surface analysis of (3aSR,10RS,10aRS)-2-(4-iodo­phen­yl)-1-oxo-5-tosyl-1,2,3,3a,4,5,10,10a-octa­hydro­pyrrolo[3,4-b]carbazole-10-carb­­oxy­lic acid–ethanol (4/1)

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Elizaveta D. Yakovleva,a Atash V. Gurbanov,b Victor N. Khrustalev,a,c Mohammed Hadi Al-Douh,d Tuncer Hökelek,e Khudayar I. Hasanovf and Roman A. Litvinovg,h*

aRUDN University, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation, bExcellence Center, Baku State University, Z. Khalilov Str. 33, AZ 1148, Baku, Azerbaijan, cZelinsky Institute of Organic Chemistry of RAS, 47 Leninsky Prospect, 119991 Moscow, Russian Federation, dChemistry Department, Faculty of Science, Hadhramout University, Mukalla, Hadhramout, Yemen, eHacettepe University, Department of Physics, 06800 Beytepe-Ankara, Türkiye, fAzerbaijan Medical University, Scientific Research Centre (SRC), A. Kasumzade St. 14, AZ 1022, Baku, Azerbaijan, gVolgograd State Medical University, 1 Pavshikh Bortsov Sq., Volgograd 400131, Russian Federation, and hLLC <<InnoVVita>>, Office 401, Room 2, 6 Komsomolskaya St., Volgograd 400066, Russian Federation
*Correspondence e-mail: [email protected]

Edited by F. Di Salvo, University of Buenos Aires, Argentina (Received 5 September 2025; accepted 23 December 2025; online 6 January 2026)

The asymmetric unit of the title compound, 4C28H23IN2O5S·C2H6O, contains two crystallographically independent mol­ecules and an ethanol solvent mol­ecule. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional architecture, enclosing R44(23) ring motifs. C—H⋯π(ring) inter­actions and the π–π stacking between the parallel rings help to consolidate the packing. Hirshfeld surface analysis reveals that the most important contributions to the crystal packing are from H⋯H (36.1% and 38.5%), H⋯O/O⋯H (23.7% and 22.1%), H⋯C/C⋯H (20.0% and 16.1%) and H⋯I/I⋯H (6.4% and 10.1%) inter­actions.

CCDC reference: 2518350

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1. Chemical context

The development of novel compounds capable of preventing the disabling consequences of fibrotic remodeling diseases represents a highly promising direction in pharmacology (Lapthorn et al., 2024View full citation). Oxidative stress is among the key factors contributing to the progression of such pathologies (Cheresh et al., 2013View full citation). The annulated iso­indole scaffold may hold considerable potential, as evidenced by data on structurally related iso­indole motifs that have demonstrated anti­oxidant and anti­fibrotic effects under experimental conditions (Yakan et al., 2023View full citation; Li et al., 2013View full citation). Prior studies have provided evidence supporting the potential of hydrogenated iso­indole-7-carb­oxy­lic acids as a scaffold for the rational design of novel agents targeting diseases associated with non-enzymatic mol­ecular damage pathways (e.g., glycation/glycoxidation) and oxidative stress, with the putative mode of action involving inhibition of oxidative processes (in particular, non-enzymatic glycation, some mechanistic steps of which are oxidation-dependent; Ibragimova et al., 2024View full citation). Subsequent elaboration of this mol­ecular core has led to the development of (3aSR,10RS,10aRS)-2-(4-iodo­phen­yl)-1-oxo-5-tosyl-1,2,3,3a,4,5,10,10a-octa­hydro­pyrrolo­[3,4-b]carbazole-10-carb­oxy­lic acid ethanol solvent (1), a new and promising representative of the series. The synthetic approach to the structures of such a type requires elaboration and an efficient and general method for constructing diverse polycycles possessing the iso­indole core. The intra­molecular Diels–Alder reaction of vinyl­arenes (IMDAV) reaction represents a highly efficient strategy, enabling single-step preparation of iso­indole derivatives annulated with various carbo- and heterocyclic frameworks (Krishna et al., 2022View full citation; Yakovleva et al., 2024View full citation). Moreover, non-covalent bond donor or acceptor attached N-compounds are of inter­est due to their high solubility in polar solvents, functional properties, photoactivity in the solid state, coordination ability, high thermal and oxidative stability, etc. (Gurbanov et al., 2018View full citation, 2023View full citation; Maharramov et al., 2010View full citation, 2011View full citation; Pronina et al., 2024View full citation). Functionalization of N-containing compounds with –COOH, –SO3H, etc. groups can improve catalytic activity and other properties (Burkin et al., 2024View full citation; Mahmudov et al., 2021View full citation, 2023View full citation).

[Scheme 1]

In a continuation of our investigations into the properties of iso­indole­carb­oxy­lic acids previously synthesized from corresponding indolyl­allyl­amines via the IMDAV reaction (Shelukho et al., 2025View full citation; Zubkov et al., 2016View full citation; Horak et al., 2015View full citation), we developed a highly efficient preparative protocol for the aromatization of [4 + 2] cyclo­addition adducts. Special emphasis was placed on optimizing the reaction conditions, leading to the identification of the most effective procedure involving acid-catalyzed isomerization in 1,2-di­chloro­ethane using an equimolar amount of hydrogen chloride in dioxane (Fig. 1[link]). The selected conditions ensure qu­anti­tative conversion of the starting materials. Moreover, the developed protocol enables complete aromatizaion of certain mixtures of non-aromatic and aromatic adducts, facilitating structural elucidation of the resulting acids. The target product was isolated in 92% yield as a white crystalline solid. For unambiguous structural confirmation and verification of the degree of aromacity, single crystals were grown by controlled slow evaporation from an ethanol–DMF mixture. X-ray diffraction analysis conclusively confirmed complete aromatization of the polycyclic system, which is consistent with NMR spectroscopic data. The developed method demonstrates excellent reproducibility and can be successfully applied to the aromatization of structurally related analogues. Herein, we report the synthesis, mol­ecular and crystal structures together with the Hirshfeld surface analysis of the title compound (I)( Fig. 2[link]).

[Figure 1]
Figure 1
Reaction scheme to obtain the title compound (I).
[Figure 2]
Figure 2
The asymmetric unit of the title compound (I) with the atom-numbering scheme and 50% probability ellipsoids, where the upper and lower mol­ecules are named as mol­ecules A and B, respectively. H atoms have been omitted for clarity.

2. Structural commentary

The asymmetric unit of the title compound (I) contains two crystallographically independent mol­ecules (A and B) and one ethanol solvent mol­ecule (Fig. 2[link]). In mol­ecules A and B, the essentially planar A (C11–C16), D (N5/C4A/C5A/C9A/C9B), E (C5A/C6–C9/C9A) (in A), and F (C17–C22) and G (C35–C40), J (N29/C28A/C29A/C33A/C33B), K (C29A/C30–C33/C33A) and L (C41–C46)] (in B) rings are oriented at dihedral angles A/D = 5.56 (9)°, A/E = 7.69 (8)°, A/F = 82.16 (7)°, D/E = 2.80 (9)°, D/F = 87.21 (8)°, E/F = 87.98 (8)°, and G/J = 17.03 (9)°, G/K = 15.76 (8)°, G/L = 70.85 (8)°, J/K = 2.08 (8)°, J/L = 87.33 (9)°, K/L = 85.63 (8)°. It is clear that the A/D and A/E dihedral angles in mol­ecule A are much narrower than the corresponding ones (G/J and G/K) in mol­ecule B. On the other hand, the A/F dihedral angle in mol­ecule A is considerably enlarged with respect to the corresponding one (G/L) in mol­ecule B due to the intra- and inter­molecular C—H⋯O and O—H⋯O hydrogen bonds (Table 1[link]). The B (N2/C1/C3/C3A/C10A and C (C3A/C4/C4A/C9B/C10/C10A) (in mol­ecule A) and H (N26/C25/C27/C27A/C34A) and I (C27A/C28/C28A/C33B/C34/C34A) (in mol­ecule B) rings exhibit envelope conformations, where atoms C3A, C10A, C27A and C34A occupy the flap positions, displaced by −0.534 (3), 0.698 (2), −0.600 (3) and 0.652 (3) Å away from the best least-squares planes of the other atoms. The O4—C24 [1.211 (3) Å], O5—C24 [1.328 (3) Å], O9—C48 [1.205 (3) Å] and O10—C48 [1.320 (3) Å] distances in the carb­oxy­lic acid moieties indicate localized single and double bonds rather than delocalized bonding arrangements. The O4—C24—O5 [123.9 (2)°] and O9—C48—O10 [123.9 (2)°] bond angles are increased with respect to that in a free acid (122.2°, Sim et al., 1955View full citation) and may be compared with the corresponding values of 124.27 (17)° in di­aqua­bis­(2-bromo­benzoato-O)bis­(nicotinamide-κN1)zinc(II) (Hökelek et al., 2009View full citation), 126.3 (3)° in trans-di­aqua­bis­(N,N-di­ethyl­nicotinamide-κN1)bis­(4-nitro­benzoato-κO)copper(II) (Hökelek et al., 1997View full citation) and 122.55 (12)° in methyl 2-oxo-1-(prop-2-yn­yl)-1,2-di­hydro­quinoline-4-carboxyl­ate (El-Mrabet et al., 2023View full citation). No unusual bond distances or inter­bond angles are observed in (I).

Table 1
Hydrogen-bond geometry (Å, °)

Cg6, Cg8 and Cg12 are the centroids of the C5A/C6–C9/C9A, C17–C22 and C41–C46 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O5—H5O⋯O6 0.85 (4) 1.80 (4) 2.640 (2) 174 (4)
C3A—H3C⋯O4 1.00 2.44 3.066 (3) 120
C6—H6⋯O3 0.95 2.32 2.913 (4) 120
C12—H12⋯O1 0.95 2.23 2.838 (3) 121
C18—H18⋯O8i 0.95 2.45 3.298 (3) 148
O10—H10O⋯O1ii 0.78 (5) 1.87 (5) 2.623 (3) 163 (5)
C27A—H27C⋯O10 1.00 2.35 3.011 (3) 123
C30—H30⋯O8 0.95 2.40 2.980 (4) 119
C36—H36⋯O6 0.95 2.35 2.895 (3) 116
O11—H11O⋯O5ii 0.90 2.12 3.024 (6) 177
C27—H27A⋯Cg8iii 0.99 2.87 3.729 (3) 145
C37—H37⋯Cg12iv 0.95 2.93 3.776 (3) 148
C39—H39⋯Cg6iii 0.95 2.70 3.526 (3) 145
Symmetry codes: (i) Mathematical equation; (ii) Mathematical equation; (iii) Mathematical equation; (iv) Mathematical equation.

3. Supra­molecular features

In the crystal, O—H⋯O and C—H⋯O hydrogen bonds (Table 1[link]) link the mol­ecules into a three-dimensional architecture, enclosing R44(23) ring motifs (Etter et al., 1990View full citation) (Fig. 3[link]). The O5—H5O⋯O6 hydrogen bond links the two independent mol­ecules in the asymmetric unit while the C18—H18⋯O8 and O10—H10O⋯O5 hydrogen bonds as well as the O11—H11O⋯O5 hydrogen bond between the solvent mol­ecule and mol­ecule A contribute to the supra­molecular behaviour. Further the C—H⋯π(ring) inter­actions and the π–π inter­actions between the F [centroid-to-centroid distance = 3.6818 (15) Å, α = 0.02 (12)° and slippage = 1.084 Å] and G rings of adjacent mol­ecules [centroid-to-centroid distance = 3.6747 (14) Å, α = 0.00 (12)° and slippage = 1.496 Å], and the D and E rings [centroid-to-centroid distance = 3.7727 (15) Å, α = 2.79 (13)° and slippage = 1.355 Å] help to consolidate the packing.

[Figure 3]
Figure 3
A partial packing diagram for the title compound (I). The O—H⋯O and C—H⋯O hydrogen bonds are shown as dashed lines. H atoms not involved in these inter­actions have been omitted for clarity.

4. Hirshfeld surface analysis

To visualize the inter­molecular inter­actions in the crystal of title compound (I), a Hirshfeld surface (HS) analysis was carried out using Crystal Explorer 17.5 (Spackman et al., 2021View full citation). In the HS plotted over dnorm (Fig. 4[link]a and b), the contact distances equal, shorter and longer with respect to the sum of van der Waals radii are shown the white, red and blue colours, respectively. According to the two-dimensional fingerprint plots, H⋯H, H⋯O/O⋯H, H⋯C/C⋯H and H⋯I/I⋯H contacts make the most important contributions to the HS (Figs. 5[link] and 6[link]), and they have significant differences due to the different numbers and values of the close contacts (see supporting information).

[Figure 4]
Figure 4
Views of the three-dimensional Hirshfeld surfaces for mol­ecules (a) A and (b) B plotted over dnorm.
[Figure 5]
Figure 5
The full two-dimensional fingerprint plots for mol­ecule A, showing (a) all inter­actions, and delineated into (b) H⋯H, (c) H⋯O/O⋯H, (d) H⋯C/C⋯H, (e) H⋯I/I⋯H, (f) C⋯I/I⋯C, (g) C⋯C, (h) H⋯N/N⋯H, (i) I⋯I, (j) O⋯O, (k) C⋯O/O⋯C, (l) O⋯I/I⋯O, (m) N⋯O/O⋯N and (n) C⋯N/N⋯C inter­actions. The di and de values are the closest inter­nal and external distances (in Å) from given points on the Hirshfeld surface.
[Figure 6]
Figure 6
The full two-dimensional fingerprint plots for mol­ecule B, showing (a) all inter­actions, and delineated into (b) H⋯H, (c) H⋯O/O⋯H, (d) H⋯C/C⋯H, (e) H⋯I/I⋯H, (f) C⋯C, (g) C⋯I/I⋯C, (h) H⋯N/N⋯H, (i) C⋯N/N⋯C, (j) I⋯I, (k) C⋯O/O⋯C and (l) O⋯O inter­actions.

5. Synthesis and crystallization

Anequimolar amount of HCl in dioxane (5.0 mol L−1; 0.250 mmol, 0.0045 mL) was added to a suspension of the starting material (3aRS,9bRS,10RS,10aRS)-2-(4-iodo­phen­yl)-5-[(4-methyl­phen­yl)sulfon­yl]-1-oxo-1,2,3,3a,4,5,10,10a-octa­hydro­pyrrolo­[3,4-b]carbozole-10-carb­oxy­lic acid (0.250 mmol, 0.13 g) in DCE (10 mL). The resulting mixture was stirred at r.t. for 24 h. The resulting precipitate was filtered off, washed with diethyl ether (5 mL), and air-dried to afford the target product (3aS,10R,10aR)-2-(4-iodo­phen­yl)-1-oxo-5-tosyl-1,2,3,3a,4,5,10,10a-octa­hydro­pyrrolo­[3,4-b]carbazole-10-carb­oxy­lic acid as white powder (0.23 mmol, 92%). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a mixture of ethanol and DMF. Yield 92%, 0.12 g; m.p. 538–543 K. 1H NMR (700 MHz, DMSO-d6, 298 K) δ 12.81 (br. s, 1H, CO2H), 8.05 (d, J = 8.3 Hz, 1H, H-Ar), 7.83 (m, J = 8.3 Hz, 2H, H-Ar), 7.78–7.71 (m, 3H, H-Ar), 7.54 (m, 2H, H-Ar), 7.40–7.25 (m, 5H, H-Ar), 4.14 (d, J = 4.0 Hz, 1H, H-10), 4.08 (t, J = 8.0 Hz, 1H, H-3), 3.80 (t, J = 10.0 Hz, 1H, H-10a), 3.59 (dd, J = 16.9, 5.0 Hz, 1H, H-3), 3.05–2.91 (m, 2H, H-3a, H-4), 2.32 (s, 3H, H-CH3) ppm 13C NMR (176.1 MHz, DMSO-d6, 298 K) δ 172.8, 172.6, 146.0, 140.0, 137.8 (2C) 136.7, 136.0, 135.1, 130.8 (2C), 129.0, 128.7 (2C), 126.9 (2C), 125.8, 125.0, 121.5, 116.4, 114.2, 88.1, 51.6, 47.1, 37.2, 32.1, 28.3, 21.5 ppm. MS (ESI): m/z = 627 [M + H]+. Analysis calculated for C28H23O5IN2S: C, 53.68; H, 3.70; O, 12.77; N, 4.47; S, 5.12; found: C, 53.51; H, 3.52; O, 12.62; N, 4.52; S, 5.32.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The OH hydrogen atoms were located in a difference-Fourier map, and refined isotropically. The C-bound hydrogen-atom positions were calculated geometrically at distances of 1.00 (for methine CH), 0.95 (for aromatic CH), 0.99 (for methyl­ene CH) and 0.98 Å (for CH3) and refined using a riding model by applying the constraint Uiso(H) = k × Ueq(C), where k = 1.5 for methyl H atoms and k = 1.2 for the other H atoms. The ethanol solvent mol­ecule is disordered relative to the inversion center. To fit its geometry to the ideal theoretical one, upon refinement the three intra­molecular distances were fixed with the accuracy of 0.003 Å: O11—C49 = 1.430 (3) Å, C49—C50 = 1.525 (3) Å and O11⋯C50 = 2.450 (3) Å. The hydrogen atom of the OH group was objectively localized in the difference-Fourier maps and refined within the riding model with fixed positional (at 0.90 Å) and isotropic displacement parameters [Uiso(H) = 1.5Ueq(O)]. The other hydrogen atoms in this mol­ecule were placed in calculated positions and refined within the riding model with fixed isotropic displacement parameters [Uiso(H) = 1.5Ueq(C) for the CH3 group and 1.2Ueq(C) for the CH2 group].

Table 2
Experimental details

Crystal data
Chemical formula 4C28H23IN2O5S·C2H6O
Mr 2551.84
Crystal system, space group Triclinic, PMathematical equation
Temperature (K) 100
a, b, c (Å) 12.39864 (18), 14.7576 (2), 15.05254 (16)
α, β, γ (°) 100.860 (1), 103.3627 (10), 98.5545 (12)
V (Å3) 2577.83 (6)
Z 1
Radiation type Cu Kα
μ (mm−1) 10.89
Crystal size (mm) 0.21 × 0.09 × 0.09
 
Data collection
Diffractometer Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector
Absorption correction Multi-scan (CrysAlis PRO; Rigaku OD, 2025View full citation)
Tmin, Tmax 0.307, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 57678, 11116, 10276
Rint 0.063
(sin θ/λ)max (Å−1) 0.639
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.103, 1.08
No. of reflections 11116
No. of parameters 703
No. of restraints 3
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.73, −1.49
Computer programs: CrysAlis PRO (Rigaku OD, 2025View full citation), SHELXT (Sheldrick, 2015aView full citation), SHELXL (Sheldrick, 2015bView full citation) and SHELXTL (Sheldrick, 2008View full citation).

Supporting information

CCDC reference: 2518350

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989025011582/vu2015sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025011582/vu2015Isup2.hkl

Supplementary tables. DOI: https://doi.org/10.1107/S2056989025011582/vu2015sup3.pdf

checkCIF report


Computing details top

(3aSR,10RS,10aRS)-2-(4-Iodophenyl)-1-oxo-5-tosyl-1,2,3,3a,4,5,10,10a-octahydropyrrolo[3,4-b]carbazole-10-carboxylic acid–ethanol (4/1) top
Crystal data top
4C28H23IN2O5S·C2H6OZ = 1
Mr = 2551.84F(000) = 1282
Triclinic, P1Dx = 1.644 Mg m−3
a = 12.39864 (18) ÅCu Kα radiation, λ = 1.54184 Å
b = 14.7576 (2) ÅCell parameters from 34693 reflections
c = 15.05254 (16) Åθ = 3.1–79.7°
α = 100.860 (1)°µ = 10.89 mm−1
β = 103.3627 (10)°T = 100 K
γ = 98.5545 (12)°Prism, colourless
V = 2577.83 (6) Å30.21 × 0.09 × 0.09 mm
Data collection top
Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector
diffractometer		10276 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tubeRint = 0.063
φ and ω scansθmax = 80.1°, θmin = 3.1°
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2025)		h = −15→15
Tmin = 0.307, Tmax = 1.000k = −18→18
57678 measured reflectionsl = −15→18
11116 independent reflections
Refinement top
Refinement on F2Primary atom site location: difference Fourier map
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: mixed
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0678P)2 + 0.6004P]
where P = (Fo2 + 2Fc2)/3
11116 reflections(Δ/σ)max = 0.001
703 parametersΔρmax = 0.73 e Å−3
3 restraintsΔρmin = −1.49 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
xyzUiso*/UeqOcc. (<1)
I10.62834 (2)1.12895 (2)0.80589 (2)0.02282 (6)
S10.80588 (5)0.67569 (4)0.03768 (4)0.01867 (12)
O10.48320 (15)0.72592 (13)0.42547 (13)0.0207 (3)
O20.80596 (18)0.77433 (14)0.05512 (13)0.0253 (4)
O30.78203 (17)0.62072 (14)−0.05633 (12)0.0231 (4)
O40.71115 (16)0.65374 (13)0.45052 (12)0.0216 (4)
O50.68875 (16)0.51002 (12)0.35881 (12)0.0199 (3)
H5O0.733 (3)0.505 (3)0.409 (3)0.030*
C10.5560 (2)0.76524 (17)0.39477 (17)0.0170 (4)
N20.61722 (17)0.85528 (15)0.42748 (14)0.0164 (4)
C30.6875 (2)0.88120 (17)0.36464 (17)0.0176 (4)
H3A0.7620660.9206500.4010390.021*
H3B0.6486550.9149510.3199480.021*
C3A0.6994 (2)0.78430 (17)0.31391 (16)0.0160 (4)
H3C0.7605870.7634250.3564320.019*
C40.7227 (2)0.77192 (17)0.21743 (17)0.0188 (5)
H4A0.6759670.8060820.1781440.023*
H4B0.8034210.7970740.2239430.023*
C4A0.6930 (2)0.66801 (17)0.17307 (16)0.0158 (4)
N50.70751 (18)0.62733 (15)0.08390 (14)0.0171 (4)
C5A0.66157 (19)0.52894 (17)0.06230 (16)0.0168 (4)
C60.6519 (2)0.4588 (2)−0.01715 (18)0.0225 (5)
H60.6826300.471500−0.0667960.027*
C70.5946 (2)0.36878 (19)−0.01997 (19)0.0236 (5)
H70.5861500.319238−0.0730550.028*
C80.5491 (2)0.34935 (19)0.05320 (19)0.0237 (5)
H80.5105310.2873730.0488230.028*
C90.5602 (2)0.41990 (18)0.13175 (18)0.0204 (5)
H90.5298710.4069480.1815290.025*
C9A0.6169 (2)0.51039 (17)0.13617 (16)0.0164 (4)
C9B0.63787 (19)0.59880 (17)0.20452 (16)0.0153 (4)
C100.59346 (19)0.61824 (16)0.29041 (16)0.0150 (4)
H100.5158550.5791060.2767180.018*
C10A0.58696 (19)0.72211 (16)0.30752 (16)0.0151 (4)
H10A0.5297750.7305720.2524030.018*
C110.6132 (2)0.91830 (17)0.50950 (17)0.0170 (4)
C120.5742 (2)0.88460 (18)0.57877 (17)0.0178 (4)
H120.5469020.8189770.5696990.021*
C130.5747 (2)0.94634 (18)0.66199 (17)0.0187 (5)
H130.5471000.9228940.7088670.022*
C140.6157 (2)1.04195 (18)0.67529 (16)0.0176 (4)
C150.6539 (2)1.07669 (17)0.60631 (17)0.0189 (4)
H150.6814241.1423530.6158970.023*
C160.6520 (2)1.01539 (18)0.52263 (17)0.0184 (4)
H160.6768171.0393980.4748940.022*
C170.9340 (2)0.65741 (18)0.10353 (17)0.0194 (5)
C181.0085 (2)0.7318 (2)0.17129 (18)0.0240 (5)
H180.9902550.7924460.1832450.029*
C191.1100 (2)0.7153 (2)0.22092 (19)0.0285 (6)
H191.1610680.7652890.2679460.034*
C201.1388 (2)0.6267 (2)0.20321 (18)0.0255 (5)
C211.0614 (2)0.5536 (2)0.13549 (17)0.0228 (5)
H211.0792210.4928500.1232230.027*
C220.9592 (2)0.56828 (18)0.08596 (17)0.0195 (5)
H220.9068980.5179100.0404200.023*
C231.2493 (3)0.6095 (3)0.2567 (2)0.0369 (7)
H23A1.3115610.6575680.2543110.055*
H23B1.2596800.5469830.2283850.055*
H23C1.2487030.6125680.3221620.055*
C240.67064 (19)0.59732 (17)0.37605 (17)0.0162 (4)
I21.11860 (2)0.79531 (2)0.96304 (2)0.02919 (7)
S21.03004 (5)0.02919 (4)0.35060 (4)0.02059 (12)
O60.83670 (16)0.49561 (14)0.51016 (13)0.0222 (4)
O71.08688 (17)0.05066 (14)0.44799 (14)0.0244 (4)
O80.98904 (18)−0.06680 (14)0.29942 (15)0.0292 (4)
O90.59404 (17)0.28231 (18)0.36431 (15)0.0323 (5)
O100.69260 (16)0.27402 (16)0.50547 (14)0.0270 (4)
H10O0.633 (4)0.270 (3)0.515 (3)0.041*
C250.8940 (2)0.43778 (18)0.53221 (16)0.0173 (4)
N260.96981 (17)0.44835 (15)0.61642 (14)0.0172 (4)
C271.0284 (2)0.36768 (18)0.61789 (17)0.0174 (4)
H27A1.0406910.3507180.6795230.021*
H27B1.1020560.3815890.6031600.021*
C27A0.94458 (19)0.28986 (17)0.54076 (16)0.0160 (4)
H27C0.8818690.2635450.5658890.019*
C280.9920 (2)0.20916 (18)0.49494 (17)0.0195 (5)
H28A1.0680480.2332620.4884400.023*
H28B0.9987130.1621000.5338410.023*
C28A0.9115 (2)0.16489 (18)0.39981 (18)0.0189 (5)
N290.91600 (19)0.07836 (16)0.34149 (15)0.0203 (4)
C29A0.8285 (2)0.06166 (18)0.25696 (18)0.0202 (5)
C300.7991 (3)−0.00993 (19)0.17547 (19)0.0258 (5)
H300.842140−0.0576120.1679560.031*
C310.7042 (3)−0.0087 (2)0.1058 (2)0.0297 (6)
H310.680860−0.0577410.0503280.036*
C320.6421 (3)0.0627 (2)0.1148 (2)0.0315 (6)
H320.5780570.0616360.0653320.038*
C330.6727 (2)0.1349 (2)0.19475 (19)0.0261 (5)
H330.6306320.1834600.2008560.031*
C33A0.7672 (2)0.13445 (18)0.26649 (18)0.0202 (5)
C33B0.8223 (2)0.19868 (18)0.35581 (17)0.0188 (5)
C340.7948 (2)0.29292 (18)0.39186 (17)0.0172 (4)
H340.7875150.3270790.3400340.021*
C34A0.8990 (2)0.34667 (17)0.47004 (16)0.0157 (4)
H34A0.9601300.3620530.4388740.019*
C351.0035 (2)0.53027 (17)0.69079 (16)0.0170 (4)
C360.9290 (2)0.59036 (19)0.70616 (17)0.0213 (5)
H360.8556500.5788610.6643050.026*
C370.9630 (2)0.6671 (2)0.78305 (18)0.0240 (5)
H370.9124930.7078730.7939240.029*
C381.0705 (2)0.68407 (19)0.84388 (17)0.0211 (5)
C391.1455 (2)0.62533 (19)0.82786 (17)0.0204 (5)
H391.2193760.6377470.8690660.025*
C401.1119 (2)0.54866 (19)0.75158 (18)0.0192 (5)
H401.1629400.5084630.7406210.023*
C411.1164 (2)0.0884 (2)0.29294 (19)0.0230 (5)
C421.1868 (2)0.1739 (2)0.3408 (2)0.0252 (5)
H421.1861700.2017670.4028350.030*
C431.2587 (2)0.2183 (2)0.2964 (2)0.0277 (6)
H431.3057530.2779100.3281020.033*
C441.2629 (2)0.1770 (2)0.2064 (2)0.0319 (6)
C451.1895 (3)0.0917 (3)0.1590 (2)0.0365 (7)
H451.1898890.0639490.0967860.044*
C461.1158 (3)0.0466 (2)0.2013 (2)0.0321 (6)
H461.065884−0.0115000.1686550.039*
C471.3487 (3)0.2237 (3)0.1635 (3)0.0414 (8)
H47A1.4252070.2231670.1995410.062*
H47B1.3403750.2888780.1647560.062*
H47C1.3359810.1892070.0984230.062*
C480.6826 (2)0.28292 (18)0.41848 (18)0.0189 (5)
O110.5545 (4)0.5639 (4)0.6475 (3)0.0417 (11)0.5
H11O0.4825010.5433930.6477640.063*0.5
C490.5758 (5)0.5140 (7)0.5644 (3)0.045 (2)0.5
H49A0.5911860.4519570.5733710.055*0.5
H49B0.6441540.5496600.5539800.055*0.5
C500.4768 (5)0.4993 (6)0.4780 (3)0.043 (2)0.5
H50A0.4873260.4528730.4264910.065*0.5
H50B0.4733770.5591170.4593750.065*0.5
H50C0.4061480.4762690.4926490.065*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02824 (10)0.02330 (10)0.01369 (9)0.00995 (7)0.00207 (6)−0.00291 (6)
S10.0247 (3)0.0202 (3)0.0135 (3)0.0097 (2)0.0067 (2)0.0036 (2)
O10.0178 (8)0.0213 (9)0.0212 (8)0.0018 (7)0.0078 (7)−0.0013 (7)
O20.0382 (11)0.0208 (9)0.0231 (9)0.0113 (8)0.0149 (8)0.0075 (7)
O30.0306 (10)0.0277 (9)0.0136 (8)0.0134 (8)0.0067 (7)0.0047 (7)
O40.0247 (9)0.0214 (9)0.0140 (8)0.0069 (7)−0.0015 (7)−0.0005 (7)
O50.0239 (9)0.0180 (8)0.0153 (8)0.0092 (7)−0.0003 (7)0.0010 (6)
C10.0150 (10)0.0186 (11)0.0162 (11)0.0070 (9)0.0022 (8)0.0004 (9)
N20.0152 (9)0.0168 (9)0.0153 (9)0.0044 (7)0.0032 (7)−0.0002 (7)
C30.0207 (11)0.0148 (11)0.0176 (11)0.0059 (9)0.0064 (9)0.0011 (9)
C3A0.0154 (10)0.0151 (10)0.0150 (11)0.0041 (8)0.0014 (8)0.0000 (8)
C40.0190 (11)0.0194 (11)0.0177 (11)0.0051 (9)0.0059 (9)0.0012 (9)
C4A0.0165 (10)0.0194 (11)0.0105 (10)0.0080 (9)0.0020 (8)−0.0003 (8)
N50.0199 (10)0.0176 (10)0.0134 (9)0.0073 (8)0.0043 (7)−0.0004 (7)
C5A0.0139 (10)0.0181 (11)0.0145 (10)0.0063 (8)−0.0018 (8)−0.0011 (9)
C60.0202 (12)0.0279 (13)0.0157 (11)0.0091 (10)−0.0001 (9)−0.0009 (10)
C70.0233 (12)0.0199 (12)0.0197 (12)0.0083 (10)−0.0030 (10)−0.0068 (9)
C80.0205 (12)0.0200 (12)0.0245 (13)0.0051 (9)−0.0007 (10)−0.0020 (10)
C90.0175 (11)0.0217 (12)0.0184 (11)0.0049 (9)0.0003 (9)0.0004 (9)
C9A0.0151 (10)0.0167 (11)0.0143 (10)0.0067 (8)−0.0013 (8)0.0000 (9)
C9B0.0148 (10)0.0180 (11)0.0117 (10)0.0070 (8)0.0007 (8)0.0005 (8)
C100.0128 (10)0.0164 (10)0.0143 (10)0.0045 (8)0.0017 (8)0.0006 (8)
C10A0.0129 (10)0.0164 (10)0.0136 (10)0.0046 (8)0.0014 (8)−0.0010 (8)
C110.0142 (10)0.0186 (11)0.0160 (11)0.0066 (8)0.0003 (8)0.0008 (9)
C120.0176 (11)0.0187 (11)0.0151 (11)0.0051 (9)0.0018 (9)0.0010 (9)
C130.0183 (11)0.0207 (12)0.0157 (11)0.0065 (9)0.0021 (9)0.0015 (9)
C140.0172 (11)0.0205 (11)0.0100 (10)0.0080 (9)−0.0032 (8)−0.0034 (8)
C150.0192 (11)0.0171 (11)0.0172 (11)0.0049 (9)0.0004 (9)0.0003 (9)
C160.0191 (11)0.0200 (11)0.0140 (10)0.0072 (9)0.0009 (8)0.0007 (9)
C170.0206 (11)0.0237 (12)0.0148 (11)0.0049 (9)0.0080 (9)0.0024 (9)
C180.0275 (13)0.0243 (12)0.0186 (12)0.0020 (10)0.0115 (10)−0.0029 (10)
C190.0232 (13)0.0351 (15)0.0190 (12)−0.0035 (11)0.0052 (10)−0.0055 (11)
C200.0191 (12)0.0409 (15)0.0143 (11)0.0041 (11)0.0046 (9)0.0027 (11)
C210.0208 (12)0.0319 (14)0.0152 (11)0.0070 (10)0.0039 (9)0.0039 (10)
C220.0201 (11)0.0215 (12)0.0143 (10)0.0031 (9)0.0029 (9)0.0012 (9)
C230.0214 (13)0.063 (2)0.0212 (13)0.0082 (14)0.0004 (11)0.0044 (14)
C240.0138 (10)0.0183 (11)0.0165 (11)0.0052 (8)0.0042 (8)0.0028 (9)
I20.03386 (11)0.02806 (11)0.01843 (10)0.00133 (7)0.00502 (7)−0.00585 (7)
S20.0219 (3)0.0174 (3)0.0221 (3)0.0065 (2)0.0062 (2)0.0012 (2)
O60.0238 (9)0.0233 (9)0.0166 (8)0.0103 (7)−0.0030 (7)0.0036 (7)
O70.0278 (9)0.0237 (9)0.0243 (9)0.0118 (8)0.0076 (8)0.0058 (7)
O80.0321 (10)0.0179 (9)0.0352 (11)0.0066 (8)0.0099 (9)−0.0018 (8)
O90.0160 (9)0.0547 (14)0.0266 (10)0.0077 (9)0.0007 (8)0.0158 (10)
O100.0145 (8)0.0477 (12)0.0194 (9)0.0086 (8)0.0046 (7)0.0069 (8)
C250.0162 (10)0.0220 (12)0.0127 (10)0.0048 (9)0.0016 (8)0.0038 (9)
N260.0165 (9)0.0199 (10)0.0142 (9)0.0081 (8)0.0006 (7)0.0022 (8)
C270.0149 (10)0.0206 (11)0.0154 (11)0.0071 (9)0.0008 (8)0.0019 (9)
C27A0.0140 (10)0.0196 (11)0.0129 (10)0.0055 (8)0.0011 (8)0.0018 (8)
C280.0178 (11)0.0201 (11)0.0177 (11)0.0073 (9)0.0003 (9)0.0003 (9)
C28A0.0186 (11)0.0193 (11)0.0181 (11)0.0043 (9)0.0048 (9)0.0023 (9)
N290.0200 (10)0.0199 (10)0.0190 (10)0.0037 (8)0.0049 (8)0.0002 (8)
C29A0.0196 (11)0.0202 (11)0.0187 (11)0.0019 (9)0.0033 (9)0.0030 (9)
C300.0308 (14)0.0200 (12)0.0223 (13)0.0015 (10)0.0060 (11)−0.0011 (10)
C310.0363 (16)0.0246 (13)0.0188 (12)−0.0029 (12)0.0023 (11)−0.0042 (10)
C320.0326 (15)0.0317 (15)0.0206 (13)0.0001 (12)−0.0021 (11)−0.0008 (11)
C330.0231 (13)0.0289 (14)0.0208 (12)0.0033 (10)−0.0001 (10)0.0010 (11)
C33A0.0190 (11)0.0213 (12)0.0169 (11)0.0019 (9)0.0031 (9)0.0001 (9)
C33B0.0169 (11)0.0209 (11)0.0166 (11)0.0041 (9)0.0031 (9)0.0015 (9)
C340.0142 (10)0.0222 (12)0.0133 (10)0.0045 (9)0.0009 (8)0.0024 (9)
C34A0.0156 (10)0.0183 (11)0.0125 (10)0.0042 (8)0.0029 (8)0.0026 (8)
C350.0177 (11)0.0197 (11)0.0115 (10)0.0044 (9)0.0007 (8)0.0021 (9)
C360.0194 (11)0.0264 (12)0.0152 (11)0.0101 (10)−0.0014 (9)0.0012 (10)
C370.0273 (13)0.0261 (13)0.0181 (12)0.0137 (10)0.0023 (10)0.0020 (10)
C380.0252 (12)0.0232 (12)0.0105 (10)0.0043 (10)0.0009 (9)−0.0012 (9)
C390.0171 (11)0.0258 (12)0.0155 (11)0.0035 (9)0.0003 (9)0.0032 (9)
C400.0161 (11)0.0249 (12)0.0176 (11)0.0073 (9)0.0032 (9)0.0063 (10)
C410.0199 (12)0.0267 (13)0.0244 (13)0.0075 (10)0.0071 (10)0.0068 (10)
C420.0225 (12)0.0271 (13)0.0285 (13)0.0112 (10)0.0077 (11)0.0061 (11)
C430.0196 (12)0.0273 (13)0.0385 (15)0.0095 (10)0.0052 (11)0.0127 (12)
C440.0218 (13)0.0466 (17)0.0351 (15)0.0145 (12)0.0066 (11)0.0236 (14)
C450.0276 (14)0.060 (2)0.0230 (14)0.0096 (14)0.0073 (11)0.0097 (14)
C460.0285 (14)0.0398 (16)0.0253 (14)0.0066 (12)0.0070 (11)0.0012 (12)
C470.0283 (15)0.066 (2)0.0407 (18)0.0131 (15)0.0105 (13)0.0328 (18)
C480.0156 (11)0.0228 (12)0.0173 (11)0.0056 (9)0.0030 (9)0.0028 (9)
O110.034 (2)0.048 (3)0.043 (3)0.014 (2)0.008 (2)0.009 (2)
C490.045 (5)0.055 (5)0.047 (5)0.018 (5)0.023 (4)0.016 (5)
C500.032 (7)0.044 (4)0.057 (8)0.003 (6)0.022 (4)0.011 (7)
Geometric parameters (Å, º) top
I1—C142.094 (2)S2—C411.761 (3)
S1—O21.4295 (19)O6—C251.233 (3)
S1—O31.4321 (19)O9—C481.205 (3)
S1—N51.674 (2)O10—C481.320 (3)
S1—C171.755 (3)O10—H10O0.78 (5)
O1—C11.226 (3)C25—N261.359 (3)
O4—C241.211 (3)C25—C34A1.505 (3)
O5—C241.328 (3)N26—C351.419 (3)
O5—H5O0.85 (4)N26—C271.485 (3)
C1—N21.366 (3)C27—C27A1.527 (3)
C1—C10A1.506 (3)C27—H27A0.9900
N2—C111.415 (3)C27—H27B0.9900
N2—C31.489 (3)C27A—C281.525 (3)
C3—C3A1.534 (3)C27A—C34A1.534 (3)
C3—H3A0.9900C27A—H27C1.0000
C3—H3B0.9900C28—C28A1.505 (3)
C3A—C10A1.523 (3)C28—H28A0.9900
C3A—C41.528 (3)C28—H28B0.9900
C3A—H3C1.0000C28A—C33B1.364 (3)
C4—C4A1.505 (3)C28A—N291.423 (3)
C4—H4A0.9900N29—C29A1.421 (3)
C4—H4B0.9900C29A—C301.394 (4)
C4A—C9B1.363 (3)C29A—C33A1.410 (4)
C4A—N51.426 (3)C30—C311.388 (4)
N5—C5A1.424 (3)C30—H300.9500
C5A—C61.395 (3)C31—C321.400 (5)
C5A—C9A1.404 (3)C31—H310.9500
C6—C71.398 (4)C32—C331.383 (4)
C6—H60.9500C32—H320.9500
C7—C81.404 (4)C33—C33A1.400 (4)
C7—H70.9500C33—H330.9500
C8—C91.385 (4)C33A—C33B1.441 (3)
C8—H80.9500C33B—C341.512 (3)
C9—C9A1.396 (4)C34—C34A1.524 (3)
C9—H90.9500C34—C481.529 (3)
C9A—C9B1.448 (3)C34—H341.0000
C9B—C101.514 (3)C34A—H34A1.0000
C10—C10A1.523 (3)C35—C401.396 (3)
C10—C241.530 (3)C35—C361.399 (3)
C10—H101.0000C36—C371.392 (4)
C10A—H10A1.0000C36—H360.9500
C11—C121.388 (3)C37—C381.389 (4)
C11—C161.403 (3)C37—H370.9500
C12—C131.402 (3)C38—C391.392 (4)
C12—H120.9500C39—C401.386 (4)
C13—C141.387 (4)C39—H390.9500
C13—H130.9500C40—H400.9500
C14—C151.386 (4)C41—C421.382 (4)
C15—C161.399 (3)C41—C461.398 (4)
C15—H150.9500C42—C431.391 (4)
C16—H160.9500C42—H420.9500
C17—C221.388 (4)C43—C441.393 (5)
C17—C181.393 (4)C43—H430.9500
C18—C191.388 (4)C44—C451.394 (5)
C18—H180.9500C44—C471.514 (4)
C19—C201.401 (4)C45—C461.391 (5)
C19—H190.9500C45—H450.9500
C20—C211.396 (4)C46—H460.9500
C20—C231.504 (4)C47—H47A0.9800
C21—C221.383 (4)C47—H47B0.9800
C21—H210.9500C47—H47C0.9800
C22—H220.9500O11—C491.428 (3)
C23—H23A0.9800O11—H11O0.9000
C23—H23B0.9800C49—C501.523 (3)
C23—H23C0.9800C49—H49A0.9900
I2—C382.091 (3)C49—H49B0.9900
S2—O71.424 (2)C50—H50A0.9800
S2—O81.433 (2)C50—H50B0.9800
S2—N291.673 (2)C50—H50C0.9800
O2—S1—O3120.60 (11)O6—C25—N26125.5 (2)
O2—S1—N5106.39 (11)O6—C25—C34A126.9 (2)
O3—S1—N5105.96 (12)N26—C25—C34A107.6 (2)
O2—S1—C17109.32 (13)C25—N26—C35126.0 (2)
O3—S1—C17108.72 (12)C25—N26—C27111.6 (2)
N5—S1—C17104.67 (11)C35—N26—C27121.86 (19)
C24—O5—H5O105 (3)N26—C27—C27A101.99 (18)
O1—C1—N2127.8 (2)N26—C27—H27A111.4
O1—C1—C10A124.3 (2)C27A—C27—H27A111.4
N2—C1—C10A107.8 (2)N26—C27—H27B111.4
C1—N2—C11124.9 (2)C27A—C27—H27B111.4
C1—N2—C3111.85 (19)H27A—C27—H27B109.2
C11—N2—C3123.3 (2)C28—C27A—C27116.95 (19)
N2—C3—C3A101.80 (19)C28—C27A—C34A111.18 (19)
N2—C3—H3A111.4C27—C27A—C34A100.81 (19)
C3A—C3—H3A111.4C28—C27A—H27C109.2
N2—C3—H3B111.4C27—C27A—H27C109.2
C3A—C3—H3B111.4C34A—C27A—H27C109.2
H3A—C3—H3B109.3C28A—C28—C27A107.44 (19)
C10A—C3A—C4110.36 (19)C28A—C28—H28A110.2
C10A—C3A—C3102.44 (19)C27A—C28—H28A110.2
C4—C3A—C3119.7 (2)C28A—C28—H28B110.2
C10A—C3A—H3C107.9C27A—C28—H28B110.2
C4—C3A—H3C107.9H28A—C28—H28B108.5
C3—C3A—H3C107.9C33B—C28A—N29108.7 (2)
C4A—C4—C3A107.1 (2)C33B—C28A—C28126.7 (2)
C4A—C4—H4A110.3N29—C28A—C28124.6 (2)
C3A—C4—H4A110.3C29A—N29—C28A107.8 (2)
C4A—C4—H4B110.3C29A—N29—S2123.48 (18)
C3A—C4—H4B110.3C28A—N29—S2124.75 (18)
H4A—C4—H4B108.5C30—C29A—C33A121.3 (2)
C9B—C4A—N5108.5 (2)C30—C29A—N29131.3 (2)
C9B—C4A—C4126.9 (2)C33A—C29A—N29107.4 (2)
N5—C4A—C4124.3 (2)C31—C30—C29A117.3 (3)
C5A—N5—C4A107.96 (19)C31—C30—H30121.4
C5A—N5—S1123.83 (17)C29A—C30—H30121.4
C4A—N5—S1123.68 (17)C30—C31—C32121.9 (3)
C6—C5A—C9A121.9 (2)C30—C31—H31119.0
C6—C5A—N5130.5 (2)C32—C31—H31119.0
C9A—C5A—N5107.5 (2)C33—C32—C31120.8 (3)
C5A—C6—C7116.6 (2)C33—C32—H32119.6
C5A—C6—H6121.7C31—C32—H32119.6
C7—C6—H6121.7C32—C33—C33A118.3 (3)
C6—C7—C8122.0 (2)C32—C33—H33120.9
C6—C7—H7119.0C33A—C33—H33120.9
C8—C7—H7119.0C33—C33A—C29A120.4 (2)
C9—C8—C7120.5 (3)C33—C33A—C33B132.2 (3)
C9—C8—H8119.8C29A—C33A—C33B107.3 (2)
C7—C8—H8119.8C28A—C33B—C33A108.6 (2)
C8—C9—C9A118.6 (2)C28A—C33B—C34124.7 (2)
C8—C9—H9120.7C33A—C33B—C34126.4 (2)
C9A—C9—H9120.7C33B—C34—C34A105.51 (19)
C9—C9A—C5A120.4 (2)C33B—C34—C48112.4 (2)
C9—C9A—C9B132.3 (2)C34A—C34—C48115.9 (2)
C5A—C9A—C9B107.3 (2)C33B—C34—H34107.5
C4A—C9B—C9A108.8 (2)C34A—C34—H34107.5
C4A—C9B—C10123.1 (2)C48—C34—H34107.5
C9A—C9B—C10127.6 (2)C25—C34A—C34119.7 (2)
C9B—C10—C10A105.48 (19)C25—C34A—C27A102.91 (18)
C9B—C10—C24112.02 (18)C34—C34A—C27A114.4 (2)
C10A—C10—C24110.88 (19)C25—C34A—H34A106.3
C9B—C10—H10109.5C34—C34A—H34A106.3
C10A—C10—H10109.5C27A—C34A—H34A106.3
C24—C10—H10109.5C40—C35—C36119.8 (2)
C1—C10A—C3A104.07 (19)C40—C35—N26118.8 (2)
C1—C10A—C10118.0 (2)C36—C35—N26121.4 (2)
C3A—C10A—C10111.74 (19)C37—C36—C35119.7 (2)
C1—C10A—H10A107.5C37—C36—H36120.1
C3A—C10A—H10A107.5C35—C36—H36120.1
C10—C10A—H10A107.5C38—C37—C36120.0 (2)
C12—C11—C16119.4 (2)C38—C37—H37120.0
C12—C11—N2120.5 (2)C36—C37—H37120.0
C16—C11—N2120.1 (2)C37—C38—C39120.4 (2)
C11—C12—C13120.7 (2)C37—C38—I2120.04 (19)
C11—C12—H12119.6C39—C38—I2119.56 (19)
C13—C12—H12119.6C40—C39—C38119.8 (2)
C14—C13—C12119.4 (2)C40—C39—H39120.1
C14—C13—H13120.3C38—C39—H39120.1
C12—C13—H13120.3C39—C40—C35120.3 (2)
C15—C14—C13120.5 (2)C39—C40—H40119.9
C15—C14—I1121.75 (18)C35—C40—H40119.9
C13—C14—I1117.60 (18)C42—C41—C46121.3 (3)
C14—C15—C16120.2 (2)C42—C41—S2119.1 (2)
C14—C15—H15119.9C46—C41—S2119.6 (2)
C16—C15—H15119.9C41—C42—C43118.9 (3)
C15—C16—C11119.7 (2)C41—C42—H42120.6
C15—C16—H16120.1C43—C42—H42120.6
C11—C16—H16120.1C42—C43—C44121.2 (3)
C22—C17—C18121.3 (2)C42—C43—H43119.4
C22—C17—S1118.7 (2)C44—C43—H43119.4
C18—C17—S1119.9 (2)C43—C44—C45118.8 (3)
C19—C18—C17118.5 (3)C43—C44—C47119.7 (3)
C19—C18—H18120.8C45—C44—C47121.5 (3)
C17—C18—H18120.8C46—C45—C44121.0 (3)
C18—C19—C20121.4 (3)C46—C45—H45119.5
C18—C19—H19119.3C44—C45—H45119.5
C20—C19—H19119.3C45—C46—C41118.8 (3)
C21—C20—C19118.4 (3)C45—C46—H46120.6
C21—C20—C23120.4 (3)C41—C46—H46120.6
C19—C20—C23121.2 (3)C44—C47—H47A109.5
C22—C21—C20121.1 (3)C44—C47—H47B109.5
C22—C21—H21119.5H47A—C47—H47B109.5
C20—C21—H21119.5C44—C47—H47C109.5
C21—C22—C17119.3 (2)H47A—C47—H47C109.5
C21—C22—H22120.4H47B—C47—H47C109.5
C17—C22—H22120.4O9—C48—O10123.9 (2)
C20—C23—H23A109.5O9—C48—C34122.7 (2)
C20—C23—H23B109.5O10—C48—C34113.5 (2)
H23A—C23—H23B109.5C49—O11—H11O109.7
C20—C23—H23C109.5O11—C49—C50112.5 (3)
H23A—C23—H23C109.5O11—C49—H49A109.1
H23B—C23—H23C109.5C50—C49—H49A109.1
O4—C24—O5123.9 (2)O11—C49—H49B109.1
O4—C24—C10124.1 (2)C50—C49—H49B109.1
O5—C24—C10112.0 (2)H49A—C49—H49B107.8
O7—S2—O8120.30 (13)C49—C50—H50A109.5
O7—S2—N29106.29 (11)C49—C50—H50B109.5
O8—S2—N29105.63 (12)H50A—C50—H50B109.5
O7—S2—C41108.47 (13)C49—C50—H50C109.5
O8—S2—C41109.40 (13)H50A—C50—H50C109.5
N29—S2—C41105.79 (12)H50B—C50—H50C109.5
C48—O10—H10O109 (3)
O1—C1—N2—C115.3 (4)O6—C25—N26—C35−5.6 (4)
C10A—C1—N2—C11−178.8 (2)C34A—C25—N26—C35170.8 (2)
O1—C1—N2—C3−173.0 (2)O6—C25—N26—C27−177.1 (2)
C10A—C1—N2—C32.9 (3)C34A—C25—N26—C27−0.7 (3)
C1—N2—C3—C3A−23.2 (2)C25—N26—C27—C27A−23.1 (3)
C11—N2—C3—C3A158.5 (2)C35—N26—C27—C27A165.0 (2)
N2—C3—C3A—C10A33.0 (2)N26—C27—C27A—C28156.6 (2)
N2—C3—C3A—C4155.4 (2)N26—C27—C27A—C34A36.0 (2)
C10A—C3A—C4—C4A−43.7 (2)C27—C27A—C28—C28A−157.2 (2)
C3—C3A—C4—C4A−162.1 (2)C34A—C27A—C28—C28A−42.2 (3)
C3A—C4—C4A—C9B10.2 (3)C27A—C28—C28A—C33B9.4 (4)
C3A—C4—C4A—N5−177.3 (2)C27A—C28—C28A—N29−169.4 (2)
C9B—C4A—N5—C5A−1.6 (3)C33B—C28A—N29—C29A2.7 (3)
C4—C4A—N5—C5A−175.2 (2)C28—C28A—N29—C29A−178.4 (2)
C9B—C4A—N5—S1−158.37 (17)C33B—C28A—N29—S2160.67 (19)
C4—C4A—N5—S127.9 (3)C28—C28A—N29—S2−20.4 (4)
O2—S1—N5—C5A164.11 (19)O7—S2—N29—C29A−170.7 (2)
O3—S1—N5—C5A34.6 (2)O8—S2—N29—C29A−41.9 (2)
C17—S1—N5—C5A−80.2 (2)C41—S2—N29—C29A74.1 (2)
O2—S1—N5—C4A−42.7 (2)O7—S2—N29—C28A34.6 (2)
O3—S1—N5—C4A−172.16 (18)O8—S2—N29—C28A163.4 (2)
C17—S1—N5—C4A73.0 (2)C41—S2—N29—C28A−80.6 (2)
C4A—N5—C5A—C6177.9 (2)C28A—N29—C29A—C30176.8 (3)
S1—N5—C5A—C6−25.3 (4)S2—N29—C29A—C3018.4 (4)
C4A—N5—C5A—C9A1.6 (2)C28A—N29—C29A—C33A−3.6 (3)
S1—N5—C5A—C9A158.34 (17)S2—N29—C29A—C33A−161.97 (18)
C9A—C5A—C6—C70.4 (4)C33A—C29A—C30—C31−2.5 (4)
N5—C5A—C6—C7−175.5 (2)N29—C29A—C30—C31177.0 (3)
C5A—C6—C7—C8−0.2 (4)C29A—C30—C31—C322.0 (4)
C6—C7—C8—C9−0.2 (4)C30—C31—C32—C33−0.6 (5)
C7—C8—C9—C9A0.3 (4)C31—C32—C33—C33A−0.2 (5)
C8—C9—C9A—C5A0.0 (3)C32—C33—C33A—C29A−0.4 (4)
C8—C9—C9A—C9B176.6 (2)C32—C33—C33A—C33B178.3 (3)
C6—C5A—C9A—C9−0.3 (3)C30—C29A—C33A—C331.8 (4)
N5—C5A—C9A—C9176.4 (2)N29—C29A—C33A—C33−177.8 (2)
C6—C5A—C9A—C9B−177.7 (2)C30—C29A—C33A—C33B−177.2 (2)
N5—C5A—C9A—C9B−1.0 (2)N29—C29A—C33A—C33B3.2 (3)
N5—C4A—C9B—C9A0.9 (3)N29—C28A—C33B—C33A−0.7 (3)
C4—C4A—C9B—C9A174.4 (2)C28—C28A—C33B—C33A−179.6 (2)
N5—C4A—C9B—C10−171.2 (2)N29—C28A—C33B—C34−175.0 (2)
C4—C4A—C9B—C102.3 (4)C28—C28A—C33B—C346.1 (4)
C9—C9A—C9B—C4A−176.9 (2)C33—C33A—C33B—C28A179.6 (3)
C5A—C9A—C9B—C4A0.0 (3)C29A—C33A—C33B—C28A−1.6 (3)
C9—C9A—C9B—C10−5.2 (4)C33—C33A—C33B—C34−6.2 (5)
C5A—C9A—C9B—C10171.7 (2)C29A—C33A—C33B—C34172.6 (2)
C4A—C9B—C10—C10A18.9 (3)C28A—C33B—C34—C34A12.7 (3)
C9A—C9B—C10—C10A−151.7 (2)C33A—C33B—C34—C34A−160.7 (2)
C4A—C9B—C10—C24−101.9 (3)C28A—C33B—C34—C48−114.6 (3)
C9A—C9B—C10—C2487.5 (3)C33A—C33B—C34—C4872.1 (3)
O1—C1—C10A—C3A−165.0 (2)O6—C25—C34A—C34−31.2 (4)
N2—C1—C10A—C3A18.9 (2)N26—C25—C34A—C34152.5 (2)
O1—C1—C10A—C10−40.5 (3)O6—C25—C34A—C27A−159.5 (2)
N2—C1—C10A—C10143.4 (2)N26—C25—C34A—C27A24.2 (2)
C4—C3A—C10A—C1−160.65 (19)C33B—C34—C34A—C25−170.2 (2)
C3—C3A—C10A—C1−32.1 (2)C48—C34—C34A—C25−45.1 (3)
C4—C3A—C10A—C1071.0 (2)C33B—C34—C34A—C27A−47.4 (3)
C3—C3A—C10A—C10−160.51 (19)C48—C34—C34A—C27A77.7 (3)
C9B—C10—C10A—C1−174.16 (19)C28—C27A—C34A—C25−161.5 (2)
C24—C10—C10A—C1−52.7 (3)C27—C27A—C34A—C25−36.9 (2)
C9B—C10—C10A—C3A−53.6 (2)C28—C27A—C34A—C3467.0 (3)
C24—C10—C10A—C3A67.9 (2)C27—C27A—C34A—C34−168.4 (2)
C1—N2—C11—C1220.6 (3)C25—N26—C35—C40−151.0 (2)
C3—N2—C11—C12−161.3 (2)C27—N26—C35—C4019.7 (3)
C1—N2—C11—C16−161.4 (2)C25—N26—C35—C3631.4 (4)
C3—N2—C11—C1616.8 (3)C27—N26—C35—C36−157.9 (2)
C16—C11—C12—C13−0.9 (4)C40—C35—C36—C37−1.2 (4)
N2—C11—C12—C13177.2 (2)N26—C35—C36—C37176.3 (2)
C11—C12—C13—C14−0.7 (4)C35—C36—C37—C380.3 (4)
C12—C13—C14—C151.3 (4)C36—C37—C38—C390.8 (4)
C12—C13—C14—I1−174.40 (17)C36—C37—C38—I2−176.9 (2)
C13—C14—C15—C16−0.4 (4)C37—C38—C39—C40−1.0 (4)
I1—C14—C15—C16175.14 (18)I2—C38—C39—C40176.72 (19)
C14—C15—C16—C11−1.2 (4)C38—C39—C40—C350.1 (4)
C12—C11—C16—C151.8 (3)C36—C35—C40—C391.0 (4)
N2—C11—C16—C15−176.3 (2)N26—C35—C40—C39−176.6 (2)
O2—S1—C17—C22−169.95 (19)O7—S2—C41—C42−31.2 (2)
O3—S1—C17—C22−36.5 (2)O8—S2—C41—C42−164.2 (2)
N5—S1—C17—C2276.4 (2)N29—S2—C41—C4282.5 (2)
O2—S1—C17—C189.5 (2)O7—S2—C41—C46146.3 (2)
O3—S1—C17—C18143.0 (2)O8—S2—C41—C4613.3 (3)
N5—S1—C17—C18−104.1 (2)N29—S2—C41—C46−100.0 (2)
C22—C17—C18—C190.6 (4)C46—C41—C42—C43−0.4 (4)
S1—C17—C18—C19−178.9 (2)S2—C41—C42—C43177.1 (2)
C17—C18—C19—C200.9 (4)C41—C42—C43—C44−1.8 (4)
C18—C19—C20—C21−1.6 (4)C42—C43—C44—C453.1 (4)
C18—C19—C20—C23179.5 (3)C42—C43—C44—C47−175.2 (3)
C19—C20—C21—C220.8 (4)C43—C44—C45—C46−2.1 (5)
C23—C20—C21—C22179.8 (3)C47—C44—C45—C46176.1 (3)
C20—C21—C22—C170.6 (4)C44—C45—C46—C410.0 (5)
C18—C17—C22—C21−1.3 (4)C42—C41—C46—C451.3 (4)
S1—C17—C22—C21178.16 (19)S2—C41—C46—C45−176.1 (2)
C9B—C10—C24—O4124.7 (3)C33B—C34—C48—O9−92.4 (3)
C10A—C10—C24—O47.2 (3)C34A—C34—C48—O9146.2 (3)
C9B—C10—C24—O5−54.7 (3)C33B—C34—C48—O1086.9 (3)
C10A—C10—C24—O5−172.29 (19)C34A—C34—C48—O10−34.6 (3)
Hydrogen-bond geometry (Å, º) top
Cg6, Cg8 and Cg12 are the centroids of the C5A/C6–C9/C9A, C17–C22 and C41–C46 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O5—H5O···O60.85 (4)1.80 (4)2.640 (2)174 (4)
C3A—H3C···O41.002.443.066 (3)120
C6—H6···O30.952.322.913 (4)120
C12—H12···O10.952.232.838 (3)121
C18—H18···O8i0.952.453.298 (3)148
O10—H10O···O1ii0.78 (5)1.87 (5)2.623 (3)163 (5)
C27A—H27C···O101.002.353.011 (3)123
C30—H30···O80.952.402.980 (4)119
C36—H36···O60.952.352.895 (3)116
O11—H11O···O5ii0.902.123.024 (6)177
C27—H27A···Cg8iii0.992.873.729 (3)145
C37—H37···Cg12iv0.952.933.776 (3)148
C39—H39···Cg6iii0.952.703.526 (3)145
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+1, −z+1.
 

Acknowledgements

The authors' contributions are as follows: conceptualization, AVG and MHAD; synthesis, EDY and RAL; X-ray analysis, AVG, VKN and TH; Hirshfeld surface analysis, TH; founding, KIH; writing (review and editing of the manuscript) AVG, EDY, RAL and TH, supervision, AVG, TH and MHAD.

Funding information

This work was supported by the Russian Science Foundation and the Administration of Volgograd oblast (project No. 24–24-20112, https://rscf.ru/project/24–24-20112/), as well as by the Baku State University and Azerbaijan Medical University. TH is also grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).

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ISSN: 2056-9890
Volume 82| Part 2| February 2026| Pages 126-131
https://doi.org/10.1107/S2056989025011582
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