Hydrogen bonds or not? Synthesis and structure of 2,3-di­cyanona­phthalene-1,4-diyl bis­(4-methylbenzene-1-sulfonate)

Akdemir, N.; Tahir, M.N.; Ashfaq, M.

doi:10.1107/S2056989026002884

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ISSN: 2056-9890

Volume 82| Part 4| April 2026| Pages 400-403

https://doi.org/10.1107/S2056989026002884

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Hydrogen bonds or not? Synthesis and structure of 2,3-dicyanonaphthalene-1,4-diyl bis(4-methylbenzene-1-sulfonate)

Nesuhi Akdemir,^a Muhammad Nawaz Tahir ^b ^* and Muhammad Ashfaq ^b

^aAmasya University, Art and Science Faculty, Department of Chemistry, 05100, İpekköy, AMASYA, Türkiye, and ^bDepartment of Physics, University of Sargodha, Sargodha 40100, Punjab, Pakistan
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 26 February 2026; accepted 19 March 2026; online 24 March 2026)

In the title compound, C₂₆H₁₈N₂O₆S₂, the pendant substituted para-toluene moieties are inclined relative to the central naphthalene-2,3-dicarbonitrile unit by 45.82 (7) and 42.41 (6)°. In the extended structure, the molecules are linked by offset parallel π–π stacking and C—H⋯π interactions to form chains that propagate along the crystallographic b-axis direction. There are no conventional hydrogen bonds according to the usual distance and angle criteria, but a Hirshfeld surface analysis shows various contacts shorter than the van der Waals radii sums of the atoms concerned. The top four contributors to the packing have percentage contributions of 26.8, 26.0, 18.7 and 17.9% for H⋯H, H⋯O, H⋯C and H⋯N, respectively.

Keywords: crystal structure; sulfonate; hydrogen bond; π-stacking.

CCDC reference: 2539097

1. Chemical context

Aryl sulfonate derivatives show interesting supramolecular behaviour in the solid state (El-Gamal et al., 2020 ). The sulfonate ester functional group is comprised of two double-bonded oxygen atoms, a single-bonded oxygen atom and carbon atom creating a polar group capable of engaging in directional intermolecular interactions (Côté & Shimizu, 2003 ; Korkmaz & Bursal, 2022 ). A number of aryl sulfonate derivatives are present in functional materials, synthetic intermediates and molecular-recognition studies (Ghazzali et al., 2013 ; Simpson & Widlanski, 2006 ; Hodges et al., 2006 ). The effect of substituents on the resultant aryl sulfonate derivatives may significantly influence the conformational behaviour, planarity and rotation of the molecules, thus determining the overall crystal packing efficiency. As part of our studies in this area, we now report the synthesis and structure of the title compound, C₂₆H₁₈N₂O₆S₂ (I).

2. Structural commentary

The crystal structure contains one molecule of (I) in the asymmetric unit (Fig. 1) in space group P $[\overline{1}]$ . As expected, the central part of the molecule (C1–C12/N1/N2) is close to planar with a root-mean-square deviation of 0.042 Å. The molecule adopts a conformation such that the central part is inclined at dihedral angles of 45.82 (7) and 42.41 (6)°, respectively, relative to the para toluene moieties (C13–C19) and (C20–C26): one lies above the central plane and one lies below. The dihedral angle between the substituted para toluene moieties is 4.30 (18)°. The C7—O1—S1—C13 and C10—O4—S2—C20 torsion angles are 91.4 (2) and −94.6 (2)°, respectively. The distorted tetrahedral geometry around the sulfur atoms in both sulfonate groups is very similar with the O=S=O bond angle [121.46 (18)° for S1 and 121.34 (14)° for S2] the largest in each case.

Figure 1
The molecular structure of (I) showing 50% probability ellipsoids.

3. Supramolecular features

In the extended structure of (I), no hydrogen-bonding interactions are observed based on the standard distance and angle criteria for such interactions but see below. The molecules are connected to each other through off-set parallel π–π stacking and C—H⋯π interactions with an inter-centroid distance of 3.9309 (15) Å and H⋯π distance of 2.93 Å. The value of the slippage distance for the offset parallel π–π stacking interaction is 1.715 Å. As the results of these interactions, a supramolecular chain is formed that propagates along the crystallographic b-axis direction (Fig. 2).

Figure 2
Fragment of a chain chain in the extended structure of (I) formed by offset parallel π–π stacking and C—H⋯π interactions. Distances shown are given in Å.

4. Hirshfeld surface analysis

A Hirshfeld surface (HS) analysis was carried out using Crystal Explorer 21.5 (Spackman et al., 2021 ). Fig. 3a shows the Hirshfeld surface plotted over d_norm, normalized distances. Red spots on the surface around an O atom of the sulfonyl group, N atoms of cyano groups, and a CH group indicate that these atoms form short-range contacts. The face-to face red and blue triangular-shaped regions/patches on the surface of the shape index plot (Fig. 3b) around the aromatic rings indicate that weak π–π interactions are present in the crystal packing (Fig. 3b). The two-dimensional fingerprint plots show that H⋯H, H⋯O, H⋯C and H⋯N contacts make the largest contributions to the packing of 26.8%, 26%, 18.7% and 17.9%, respectively (Fig. 4a–d).

Figure 3
The Hirshfeld surface of (I) plotted over (a) d_norm and (b) shape-index. Short contacts associated with red spots in the d_norm plot include O2⋯H2 (2.69 Å), O2⋯C25 (3.15 Å), N2⋯H3 (2.69 Å) and N1⋯C21 (3.41 Å).

Figure 4
The two-dimensional fingerprint plots for (I) showing: (a)–(d) the top four contributing percentage contacts and (e)–(h) associated Hirshfeld surfaces.

5. Database survey

A survey of the Cambridge Structural Database (CSD 6.0.1 updated November 2025; Groom et al., 2015 ) found two structures having sulfonate groups attached to a naphthalene fused-ring system, viz. CSD refcodes HUSYAX (Hassan et al., 2015 ) and WUFYAX (Yang et al., 2002 ). Three polymorphs of the central naphthalene-2,3-dicarbonitrile group in the present compound have also been published [XEJNOV (Janczak & Kubiak, 2000 ), XEJNOV01 (Pitchumony & Stoeckli-Evans, 2005 ) and XEJNOV02 (Marsh, 2005 )].

The bond lengths and bond angles of the present structure are consistent with corresponding ones in above-mentioned reported structures. The geometry around the sulfur atoms in HUSYAX and WUFYAX is distorted tetrahedral, just as observed in the present structure. The central part of the molecule in HUSYAX and WUFYAX is almost planar, with r.m.s. deviations of 0.042 and 0.043 Å, respectively.

6. Interaction energy calculations and energy frameworks

The calculation of the intermolecular interaction energies using Crystal Explorer (Spackman et al., 2021) provides a quantitative understanding of the types of forces that contribute to the aggregation of molecules in the extended structure. By decomposing the overall intermolecular interaction energy into the electrostatic, polarization, dispersive, and repulsion components, the identification of dominant stabilizing intermolecular interactions is now possible (Mackenzie et al., 2017 ; Turner et al., 2014 ). The maximum attractive interaction for (I) occurs when the centroid-to-centroid distance between the molecular pair is 5.71 Å with a total energy (E_total) of −68.6 kJ mol⁻¹ (Table S1). The total energy of the interaction is dominated by a dispersion component (E_disp = −87.6 kJ mol⁻¹), significantly larger than its repulsion contribution (E_rep = +43.3 kJ mol⁻¹). Other close stabilizing contacts at centroid-to-centroid distances of 6.82, 8.11, and 9.98 Å are seen, with total energies of −53.7, −49.8 and −45.5 kJ mol⁻¹, respectively, exhibiting complementary electrostatic and dispersion contributions. The energy framework plots of the crystal structure demonstrate that the dispersion energy contributes the most to the overall energy of the crystal structure as shown in the supporting information (Fig. S2a–c).

7. Synthesis and crystallization

4-Methylbenzene-1-sulfonyl chloride (2.04 g, 9.71 mmol), 1,4-dihydroxynaphthalene-2,3-dicarbonitrile (4.39 g, 23.0 mmol) and K₂CO₃ (6 g, 43 mmol) in acetone (150 ml) were refluxed for 5 h and stirred under a nitrogen atmosphere (Fig. 5). The reaction mixture was cooled and poured into ice–water (250 g). The product was filtered off and washed with 10% (w/w) NaOH solution and water until the filtrate was neutral and dried: yield = 5.04 g, 85.2%, m.p. 463 K. Single crystals of (I) in the form of orange blocks were obtained from acetonitrile solution at room temperature by slow evaporation. FT-IR (cm⁻¹): 3053 (aromatic CH), 2977 (aliphatic CH), 2236 (C≡N) 1358 (sulfonyl ν_asym) and 1175 (sulfonyl ν_sym) (Fig. S3).

Figure 5
Reaction scheme.

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. The hydrogen atom positions were calculated geometrically at distances of 0.93 Å (for aromatic CH) and 0.96 Å (for CH₃) and refined using a riding model with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C).

Table 1
Experimental details

Crystal data
Chemical formula	C₂₆H₁₈N₂O₆S₂
M_r	518.54
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	9.9829 (7), 10.8324 (8), 12.6366 (10)
α, β, γ (°)	108.467 (3), 90.006 (3), 111.812 (2)
V (Å³)	1192.53 (16)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.27
Crystal size (mm)	0.21 × 0.17 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.619, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	29617, 4856, 4032
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.126, 1.16
No. of reflections	4856
No. of parameters	328
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.30
Computer programs: APEX2 and SAINT (Bruker, 2014 ), SHELXT2014/5 (Sheldrick, 2015a ), SHELXL2025/1 (Sheldrick, 2015b ), Mercury (Macrae et al., 2020 ) and DIAMOND (Brandenburg & Putz, 2005 ).

Supporting information

CCDC reference: 2539097

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026002884/hb8198sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026002884/hb8198Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026002884/hb8198sup4.docx

Supporting information file. DOI: https://doi.org/10.1107/S2056989026002884/hb8198Isup4.cml

checkCIF report

Computing details top

2,3-Dicyanonaphthalene-1,4-diyl bis(4-methylbenzene-1-sulfonate) top

Crystal data top

C₂₆H₁₈N₂O₆S₂	Z = 2
M_r = 518.54	F(000) = 536
Triclinic, P1	D_x = 1.444 Mg m⁻³
a = 9.9829 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8324 (8) Å	Cell parameters from 4032 reflections
c = 12.6366 (10) Å	θ = 3.0–26.5°
α = 108.467 (3)°	µ = 0.27 mm⁻¹
β = 90.006 (3)°	T = 293 K
γ = 111.812 (2)°	Block, orange
V = 1192.53 (16) Å³	0.21 × 0.17 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	4032 reflections with I > 2σ(I)
Detector resolution: 0.7979 pixels mm^-1	R_int = 0.049
ω scans	θ_max = 26.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −12→12
T_min = 0.619, T_max = 0.745	k = −13→13
29617 measured reflections	l = −15→15
4856 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.057	w = 1/[σ²(F_o²) + (0.0197P)² + 1.3252P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.126	(Δ/σ)_max < 0.001
S = 1.16	Δρ_max = 0.36 e Å⁻³
4856 reflections	Δρ_min = −0.30 e Å⁻³
328 parameters	Extinction correction: SHELXL-2025/1 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.049 (2)
Primary atom site location: dual

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
S1	0.38243 (8)	0.62969 (7)	0.88565 (6)	0.0516 (2)
S2	0.14200 (7)	0.02617 (7)	0.30348 (6)	0.03969 (19)
O1	0.3124 (2)	0.45839 (18)	0.81957 (14)	0.0408 (4)
O2	0.4683 (2)	0.6927 (2)	0.8127 (2)	0.0718 (7)
O3	0.4454 (3)	0.6399 (3)	0.9900 (2)	0.0881 (9)
O4	0.21202 (19)	0.20023 (17)	0.35525 (14)	0.0371 (4)
O5	0.0730 (2)	−0.0232 (2)	0.38872 (18)	0.0548 (5)
O6	0.0617 (2)	−0.0017 (2)	0.20035 (17)	0.0605 (6)
N1	−0.0626 (2)	0.3710 (3)	0.75159 (19)	0.0478 (6)
N2	−0.1281 (3)	0.2042 (3)	0.4258 (2)	0.0618 (7)
C1	0.5529 (3)	0.4413 (3)	0.7005 (3)	0.0530 (8)
H1	0.571033	0.481170	0.778571	0.064*
C2	0.6637 (3)	0.4311 (3)	0.6397 (3)	0.0650 (10)
H2	0.757451	0.465769	0.676913	0.078*
C3	0.6387 (3)	0.3697 (3)	0.5227 (3)	0.0610 (9)
H3	0.716230	0.365652	0.482937	0.073*
C4	0.5018 (3)	0.3153 (3)	0.4658 (3)	0.0465 (7)
H4	0.486208	0.273185	0.387834	0.056*
C5	0.3839 (3)	0.3232 (2)	0.5255 (2)	0.0344 (5)
C6	0.4107 (3)	0.3910 (2)	0.6445 (2)	0.0361 (6)
C7	0.2924 (3)	0.4036 (2)	0.7029 (2)	0.0327 (5)
C8	0.1547 (2)	0.3531 (2)	0.64783 (19)	0.0295 (5)
C9	0.1278 (2)	0.2831 (2)	0.52832 (19)	0.0298 (5)
C10	0.2402 (3)	0.2674 (2)	0.47140 (19)	0.0309 (5)
C11	0.0351 (3)	0.3641 (3)	0.70744 (19)	0.0336 (5)
C12	−0.0152 (3)	0.2354 (3)	0.4705 (2)	0.0389 (6)
C13	0.2307 (3)	0.6736 (3)	0.9029 (2)	0.0401 (6)
C14	0.1866 (3)	0.7227 (3)	0.8263 (2)	0.0456 (6)
H14	0.238631	0.734739	0.766786	0.055*
C15	0.0644 (3)	0.7532 (3)	0.8397 (2)	0.0497 (7)
H15	0.034337	0.786661	0.788666	0.060*
C16	−0.0151 (3)	0.7352 (3)	0.9278 (2)	0.0456 (6)
C17	0.0333 (3)	0.6884 (3)	1.0036 (2)	0.0500 (7)
H17	−0.017879	0.677738	1.063739	0.060*
C18	0.1554 (3)	0.6570 (3)	0.9928 (2)	0.0472 (7)
H18	0.186455	0.625412	1.044743	0.057*
C19	−0.1493 (4)	0.7677 (4)	0.9419 (3)	0.0708 (10)
H19A	−0.122396	0.865196	0.987111	0.106*
H19B	−0.214557	0.708540	0.978208	0.106*
H19C	−0.196601	0.749963	0.869335	0.106*
C20	0.2954 (3)	−0.0147 (2)	0.2792 (2)	0.0332 (5)
C21	0.3516 (3)	−0.0549 (3)	0.3559 (2)	0.0424 (6)
H21	0.307498	−0.062599	0.419600	0.051*
C22	0.4745 (3)	−0.0835 (3)	0.3364 (2)	0.0482 (7)
H22	0.513505	−0.110111	0.388143	0.058*
C23	0.5413 (3)	−0.0737 (3)	0.2417 (2)	0.0453 (7)
C24	0.4815 (3)	−0.0337 (3)	0.1663 (2)	0.0463 (7)
H24	0.525008	−0.026795	0.102164	0.056*
C25	0.3588 (3)	−0.0036 (3)	0.1834 (2)	0.0400 (6)
H25	0.319824	0.023477	0.132009	0.048*
C26	0.6732 (3)	−0.1085 (4)	0.2196 (3)	0.0671 (10)
H26A	0.643189	−0.206686	0.175093	0.101*
H26B	0.726899	−0.089700	0.289921	0.101*
H26C	0.733834	−0.051388	0.179810	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0441 (4)	0.0375 (4)	0.0543 (4)	0.0164 (3)	−0.0115 (3)	−0.0095 (3)
S2	0.0377 (3)	0.0320 (3)	0.0413 (4)	0.0144 (3)	0.0068 (3)	0.0012 (3)
O1	0.0504 (11)	0.0338 (9)	0.0321 (9)	0.0182 (8)	−0.0060 (8)	0.0015 (7)
O2	0.0510 (13)	0.0369 (11)	0.111 (2)	0.0110 (10)	0.0247 (13)	0.0111 (12)
O3	0.0908 (18)	0.0875 (18)	0.0627 (15)	0.0547 (16)	−0.0434 (13)	−0.0281 (13)
O4	0.0487 (10)	0.0309 (9)	0.0323 (9)	0.0191 (8)	0.0112 (7)	0.0075 (7)
O5	0.0551 (12)	0.0371 (10)	0.0689 (14)	0.0163 (9)	0.0323 (10)	0.0159 (9)
O6	0.0549 (12)	0.0638 (14)	0.0504 (12)	0.0328 (11)	−0.0119 (10)	−0.0080 (10)
N1	0.0406 (13)	0.0582 (15)	0.0376 (12)	0.0188 (11)	0.0093 (10)	0.0080 (11)
N2	0.0503 (15)	0.085 (2)	0.0430 (14)	0.0363 (14)	−0.0056 (12)	0.0020 (13)
C1	0.0392 (15)	0.0435 (16)	0.067 (2)	0.0204 (13)	−0.0100 (13)	0.0017 (14)
C2	0.0344 (15)	0.0498 (18)	0.101 (3)	0.0201 (14)	−0.0056 (16)	0.0093 (18)
C3	0.0362 (15)	0.0443 (17)	0.099 (3)	0.0195 (13)	0.0195 (16)	0.0151 (17)
C4	0.0408 (15)	0.0314 (13)	0.0658 (18)	0.0172 (11)	0.0188 (13)	0.0112 (12)
C5	0.0343 (12)	0.0228 (11)	0.0469 (14)	0.0146 (10)	0.0089 (11)	0.0087 (10)
C6	0.0331 (12)	0.0249 (11)	0.0483 (14)	0.0145 (10)	0.0001 (10)	0.0063 (10)
C7	0.0380 (13)	0.0236 (11)	0.0338 (12)	0.0127 (10)	−0.0020 (10)	0.0055 (9)
C8	0.0309 (12)	0.0254 (11)	0.0317 (12)	0.0131 (9)	0.0036 (9)	0.0068 (9)
C9	0.0314 (12)	0.0277 (11)	0.0299 (12)	0.0136 (9)	0.0025 (9)	0.0070 (9)
C10	0.0393 (13)	0.0237 (11)	0.0309 (12)	0.0151 (10)	0.0068 (10)	0.0075 (9)
C11	0.0346 (13)	0.0328 (12)	0.0270 (12)	0.0117 (10)	−0.0002 (10)	0.0039 (9)
C12	0.0422 (15)	0.0470 (15)	0.0263 (12)	0.0239 (12)	0.0035 (10)	0.0033 (11)
C13	0.0450 (14)	0.0307 (12)	0.0351 (13)	0.0135 (11)	−0.0024 (11)	0.0003 (10)
C14	0.0534 (16)	0.0439 (15)	0.0398 (14)	0.0196 (13)	0.0122 (12)	0.0141 (12)
C15	0.0597 (18)	0.0547 (17)	0.0454 (16)	0.0299 (15)	0.0071 (13)	0.0221 (14)
C16	0.0461 (15)	0.0416 (15)	0.0433 (15)	0.0177 (12)	0.0050 (12)	0.0065 (12)
C17	0.0592 (18)	0.0486 (16)	0.0367 (14)	0.0189 (14)	0.0118 (13)	0.0103 (12)
C18	0.0659 (19)	0.0398 (15)	0.0320 (13)	0.0206 (14)	−0.0026 (12)	0.0072 (11)
C19	0.056 (2)	0.089 (3)	0.069 (2)	0.0377 (19)	0.0122 (17)	0.0162 (19)
C20	0.0370 (13)	0.0243 (11)	0.0332 (12)	0.0124 (10)	0.0069 (10)	0.0028 (9)
C21	0.0511 (16)	0.0391 (14)	0.0357 (14)	0.0167 (12)	0.0077 (11)	0.0122 (11)
C22	0.0538 (17)	0.0423 (15)	0.0497 (16)	0.0232 (13)	−0.0022 (13)	0.0120 (13)
C23	0.0364 (14)	0.0287 (13)	0.0586 (17)	0.0113 (11)	0.0024 (12)	0.0010 (12)
C24	0.0496 (16)	0.0408 (15)	0.0457 (15)	0.0186 (13)	0.0178 (13)	0.0100 (12)
C25	0.0465 (15)	0.0377 (14)	0.0367 (13)	0.0185 (12)	0.0089 (11)	0.0116 (11)
C26	0.0451 (17)	0.057 (2)	0.090 (3)	0.0273 (15)	0.0055 (16)	0.0045 (18)

Geometric parameters (Å, º) top

S1—O3	1.415 (2)	C13—C14	1.383 (4)
S1—O2	1.419 (3)	C13—C18	1.385 (4)
S1—O1	1.6382 (18)	C14—C15	1.375 (4)
S1—C13	1.743 (3)	C14—H14	0.9300
S2—O6	1.415 (2)	C15—C16	1.390 (4)
S2—O5	1.418 (2)	C15—H15	0.9300
S2—O4	1.6464 (17)	C16—C17	1.377 (4)
S2—C20	1.747 (2)	C16—C19	1.503 (4)
O1—C7	1.387 (3)	C17—C18	1.378 (4)
O4—C10	1.391 (3)	C17—H17	0.9300
N1—C11	1.138 (3)	C18—H18	0.9300
N2—C12	1.140 (3)	C19—H19A	0.9600
C1—C2	1.365 (4)	C19—H19B	0.9600
C1—C6	1.412 (3)	C19—H19C	0.9600
C1—H1	0.9300	C20—C21	1.375 (4)
C2—C3	1.394 (5)	C20—C25	1.385 (3)
C2—H2	0.9300	C21—C22	1.377 (4)
C3—C4	1.366 (4)	C21—H21	0.9300
C3—H3	0.9300	C22—C23	1.385 (4)
C4—C5	1.413 (3)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.382 (4)
C5—C10	1.408 (3)	C23—C26	1.502 (4)
C5—C6	1.423 (4)	C24—C25	1.380 (4)
C6—C7	1.419 (3)	C24—H24	0.9300
C7—C8	1.368 (3)	C25—H25	0.9300
C8—C9	1.432 (3)	C26—H26A	0.9600
C8—C11	1.434 (3)	C26—H26B	0.9600
C9—C10	1.368 (3)	C26—H26C	0.9600
C9—C12	1.432 (3)

O3—S1—O2	121.46 (18)	C14—C13—S1	119.7 (2)
O3—S1—O1	101.94 (13)	C18—C13—S1	119.1 (2)
O2—S1—O1	107.23 (12)	C15—C14—C13	118.9 (3)
O3—S1—C13	110.58 (15)	C15—C14—H14	120.6
O2—S1—C13	110.13 (14)	C13—C14—H14	120.6
O1—S1—C13	103.64 (11)	C14—C15—C16	121.4 (3)
O6—S2—O5	121.34 (14)	C14—C15—H15	119.3
O6—S2—O4	102.41 (12)	C16—C15—H15	119.3
O5—S2—O4	107.33 (10)	C17—C16—C15	118.2 (3)
O6—S2—C20	110.53 (12)	C17—C16—C19	120.4 (3)
O5—S2—C20	110.27 (13)	C15—C16—C19	121.4 (3)
O4—S2—C20	103.03 (10)	C16—C17—C18	121.9 (3)
C7—O1—S1	120.59 (16)	C16—C17—H17	119.0
C10—O4—S2	119.14 (15)	C18—C17—H17	119.0
C2—C1—C6	119.8 (3)	C17—C18—C13	118.4 (3)
C2—C1—H1	120.1	C17—C18—H18	120.8
C6—C1—H1	120.1	C13—C18—H18	120.8
C1—C2—C3	121.1 (3)	C16—C19—H19A	109.5
C1—C2—H2	119.5	C16—C19—H19B	109.5
C3—C2—H2	119.5	H19A—C19—H19B	109.5
C4—C3—C2	120.9 (3)	C16—C19—H19C	109.5
C4—C3—H3	119.6	H19A—C19—H19C	109.5
C2—C3—H3	119.6	H19B—C19—H19C	109.5
C3—C4—C5	119.9 (3)	C21—C20—C25	121.6 (2)
C3—C4—H4	120.1	C21—C20—S2	119.66 (19)
C5—C4—H4	120.1	C25—C20—S2	118.8 (2)
C10—C5—C4	122.3 (2)	C20—C21—C22	118.7 (2)
C10—C5—C6	118.5 (2)	C20—C21—H21	120.6
C4—C5—C6	119.1 (2)	C22—C21—H21	120.6
C1—C6—C7	122.3 (2)	C21—C22—C23	121.6 (3)
C1—C6—C5	119.1 (2)	C21—C22—H22	119.2
C7—C6—C5	118.6 (2)	C23—C22—H22	119.2
C8—C7—O1	118.1 (2)	C24—C23—C22	118.1 (3)
C8—C7—C6	121.8 (2)	C24—C23—C26	120.6 (3)
O1—C7—C6	119.9 (2)	C22—C23—C26	121.3 (3)
C7—C8—C9	119.5 (2)	C25—C24—C23	121.8 (3)
C7—C8—C11	121.6 (2)	C25—C24—H24	119.1
C9—C8—C11	118.9 (2)	C23—C24—H24	119.1
C10—C9—C8	119.3 (2)	C24—C25—C20	118.2 (3)
C10—C9—C12	121.4 (2)	C24—C25—H25	120.9
C8—C9—C12	119.3 (2)	C20—C25—H25	120.9
C9—C10—O4	118.4 (2)	C23—C26—H26A	109.5
C9—C10—C5	122.3 (2)	C23—C26—H26B	109.5
O4—C10—C5	119.2 (2)	H26A—C26—H26B	109.5
N1—C11—C8	177.9 (3)	C23—C26—H26C	109.5
N2—C12—C9	176.6 (3)	H26A—C26—H26C	109.5
C14—C13—C18	121.2 (3)	H26B—C26—H26C	109.5

O3—S1—O1—C7	−153.7 (2)	C4—C5—C10—C9	−175.7 (2)
O2—S1—O1—C7	−25.1 (2)	C6—C5—C10—C9	3.7 (3)
C13—S1—O1—C7	91.4 (2)	C4—C5—C10—O4	0.9 (3)
O6—S2—O4—C10	150.60 (18)	C6—C5—C10—O4	−179.7 (2)
O5—S2—O4—C10	21.8 (2)	O3—S1—C13—C14	155.5 (2)
C20—S2—O4—C10	−94.61 (18)	O2—S1—C13—C14	18.5 (3)
C6—C1—C2—C3	−1.0 (5)	O1—S1—C13—C14	−96.0 (2)
C1—C2—C3—C4	−1.3 (5)	O3—S1—C13—C18	−25.3 (3)
C2—C3—C4—C5	1.1 (4)	O2—S1—C13—C18	−162.3 (2)
C3—C4—C5—C10	−179.2 (3)	O1—S1—C13—C18	83.3 (2)
C3—C4—C5—C6	1.4 (4)	C18—C13—C14—C15	−0.9 (4)
C2—C1—C6—C7	−177.6 (3)	S1—C13—C14—C15	178.3 (2)
C2—C1—C6—C5	3.5 (4)	C13—C14—C15—C16	−0.3 (4)
C10—C5—C6—C1	176.9 (2)	C14—C15—C16—C17	1.3 (4)
C4—C5—C6—C1	−3.7 (4)	C14—C15—C16—C19	−179.5 (3)
C10—C5—C6—C7	−2.1 (3)	C15—C16—C17—C18	−1.2 (4)
C4—C5—C6—C7	177.3 (2)	C19—C16—C17—C18	179.6 (3)
S1—O1—C7—C8	−102.8 (2)	C16—C17—C18—C13	0.1 (4)
S1—O1—C7—C6	82.1 (2)	C14—C13—C18—C17	1.0 (4)
C1—C6—C7—C8	−179.2 (2)	S1—C13—C18—C17	−178.2 (2)
C5—C6—C7—C8	−0.3 (3)	O6—S2—C20—C21	−151.9 (2)
C1—C6—C7—O1	−4.3 (4)	O5—S2—C20—C21	−15.0 (2)
C5—C6—C7—O1	174.6 (2)	O4—S2—C20—C21	99.3 (2)
O1—C7—C8—C9	−173.8 (2)	O6—S2—C20—C25	29.1 (2)
C6—C7—C8—C9	1.2 (3)	O5—S2—C20—C25	166.04 (19)
O1—C7—C8—C11	4.0 (3)	O4—S2—C20—C25	−79.7 (2)
C6—C7—C8—C11	179.0 (2)	C25—C20—C21—C22	0.4 (4)
C7—C8—C9—C10	0.4 (3)	S2—C20—C21—C22	−178.5 (2)
C11—C8—C9—C10	−177.5 (2)	C20—C21—C22—C23	−0.4 (4)
C7—C8—C9—C12	−177.5 (2)	C21—C22—C23—C24	0.2 (4)
C11—C8—C9—C12	4.6 (3)	C21—C22—C23—C26	−178.5 (3)
C8—C9—C10—O4	−179.5 (2)	C22—C23—C24—C25	0.1 (4)
C12—C9—C10—O4	−1.6 (3)	C26—C23—C24—C25	178.8 (3)
C8—C9—C10—C5	−2.9 (3)	C23—C24—C25—C20	−0.2 (4)
C12—C9—C10—C5	175.0 (2)	C21—C20—C25—C24	−0.1 (4)
S2—O4—C10—C9	−82.1 (2)	S2—C20—C25—C24	178.83 (19)
S2—O4—C10—C5	101.2 (2)

Acknowledgements

The authors acknowledge the Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2014). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Côté, A. P. & Shimizu, G. K. H. (2003). Coord. Chem. Rev. 245, 49–64. Web of Science CrossRef CAS Google Scholar
El-Gamal, M. I., Zaraei, S.-O., Foster, P. A., Anbar, H. S., El-Gamal, R., El-Awady, R. & Potter, B. V. L. (2020). Bioorg. Med. Chem. 28, 115406. PubMed Google Scholar
Ghazzali, M., Khattab, S. A. N., Elnakady, Y. A., Al-Mekhlafi, F. A., Al-Farhan, K. & El-Faham, A. (2013). J. Mol. Struct. 1046, 147–152. Web of Science CSD CrossRef 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
Hassan, Z., Al-Shidhani, S., Al-Ghafri, A., Al-Harrasi, A., Hussain, J. & Csuk, R. (2015). Tetrahedron Lett. 56, 7141–7144. CSD CrossRef CAS Google Scholar
Hodges, G., Roberts, D. W., Marshall, S. J. & Dearden, J. C. (2006). Chemosphere 63, 1443–1450. CrossRef PubMed CAS Google Scholar
Janczak, J. & Kubiak, R. (2000). J. Mol. Struct. 516, 81–90. Web of Science CSD CrossRef CAS Google Scholar
Korkmaz, A. & Bursal, E. (2022). Chem. Biodivers. 19, e202200140. CrossRef PubMed Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Mackenzie, C. F., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). IUCrJ 4, 575–587. Web of Science CrossRef CAS PubMed IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Marsh, R. E. (2005). Acta Cryst. B61, 359–359. CSD CrossRef CAS IUCr Journals Google Scholar
Pitchumony, T. S. & Stoeckli-Evans, H. (2005). Acta Cryst. E61, o40–o41. Web of Science 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
Simpson, L. S. & Widlanski, T. S. (2006). J. Am. Chem. Soc. 128, 1605–1610. CrossRef PubMed CAS 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
Turner, M. J., Grabowsky, S., Jayatilaka, D. & Spackman, M. A. (2014). J. Phys. Chem. Lett. 5, 4249–4255. Web of Science CrossRef CAS PubMed Google Scholar
Yang, J.-S., Liu, C.-P., Lin, B.-C., Tu, C.-W. & Lee, G.-H. (2002). J. Org. Chem. 67, 7343–7354. CSD CrossRef PubMed CAS Google Scholar

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