Crystal structure and Hirshfeld surface analysis of 4-cyano-N-[(4-cyano­phen­yl)sulfon­yl]-N-[2-(5-methyl­furan-2-yl)phen­yl]benzene­sulfonamide

Mammadova, G.Z.; Yakovleva, E.D.; Burkin, G.M.; Khrustalev, V.N.; Akkurt, M.; Çelikesir, S.T.; Bhattarai, A.

doi:10.1107/S2056989023006254

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ISSN: 2056-9890

Volume 79| Part 8| August 2023| Pages 747-751

https://doi.org/10.1107/S2056989023006254

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Crystal structure and Hirshfeld surface analysis of 4-cyano-N-[(4-cyanophenyl)sulfonyl]-N-[2-(5-methylfuran-2-yl)phenyl]benzenesulfonamide

Gunay Z. Mammadova,^a Elizaveta D. Yakovleva,^b Gleb M. Burkin,^b Victor N. Khrustalev,^b,^c Mehmet Akkurt,^d ^* Sevim Türktekin Çelikesir ^d and Ajaya Bhattarai ^e ^*

^aOrganic Chemistry Department, Baku State University, Z. Xalilov Str. 23, Az 1148 Baku, Azerbaijan, ^bPeoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation, ^cZelinsky Institute of Organic Chemistry of RAS, 4, 7 Leninsky Prospect, 119991 Moscow, Russian Federation, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, and ^eDepartment of Chemistry, M.M.A.M.C (Tribhuvan University), Biratnagar, Nepal
^*Correspondence e-mail: akkurt@erciyes.edu.tr, ajaya.bhattarai@mmamc.tu.edu.np

Edited by B. Therrien, University of Neuchâtel, Switzerland (Received 5 July 2023; accepted 17 July 2023; online 21 July 2023)

In the title compound, C₂₅H₁₇N₃O₅S₂, intramolecular π–π interactions [centroid-to-centroid distance = 3.5640 (9) Å] 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⋯π interactions and weak van der Waals interactions. Hirshfeld surface analysis indicates that H⋯H (30.2%), N⋯H/H⋯N (22.3%), C⋯H/H⋯C (17.9%) and O⋯H/H⋯O (15.4%) interactions make the most significant contributions to the crystal packing.

Keywords: crystal structure; sulfonamides; hydrogen bonds; C—H⋯π interactions; π–π interactions; Hirshfeld surface analysis.

CCDC reference: 2282070

1. Chemical context

The famous Hinsberg reaction, first described by Oscar Hinsberg in 1890 (Hinsberg, 1890 ; Hinsberg & Kessler, 1905 ), is a laboratory test used for the detection of primary, secondary and tertiary amines. In this reaction, the corresponding amine is shaken with benzyl or p-tolylsulfonyl chloride in the presence of an aqueous base. Reactions with ammonia, and primary and secondary amines are the most widespread. A primary amine will form a soluble sulfonamide salt in the presence of aqueous alkali (either KOH or NaOH). A secondary amine in the same reaction forms an insoluble sulfonamide. The most widely used sulfonylamide is sulfanilamide, an antibacterial drug that was first obtained in 1908 by the Austrian chemist Paul Josef Jakob Gelmo while he was trying to synthesize a dye for textile materials (Gelmo, 1908 ). Moreover, sulfonylamides are active against seizures (Thiry et al., 2008 ), and inhibit various enzymes such as human leukocyte elastase, cathespin G and HIV-1 protease (Supuran et al., 2003 ). Sulfonamides are also used in fungicidal (Chohan et al., 2006 , 2010 ) and insecticidal mixtures (Beesley & Peters, 1971 ). The number of donor and acceptor groups is a fundamental molecular descriptor to predict the oral bioavailability as well as biocatalytic activity of small drug candidates (Gurbanov et al., 2020a ,b , 2022 ; Mahmoudi et al., 2017a ,b ). Continuing our research in the improved multiple displacement amplification (IMDA) reaction field (Mammadova et al., 2023 ; Krishna et al., 2022 ; Yarovaya et al., 2021 ), in this work we have studied the interaction of 2-(α-furyl)aniline with sulfochloride containing an electron-withdrawing 4-cyanophenyl group. Unexpectedly, under mild reaction conditions, the product of a double sulfarylation was isolated in good yield from the reaction mixture (Fig. 1). The formation of such double sulfonamide was previously observed in the presence of strong bases (Bartsch et al., 1977 ; Li et al., 2022 ).

Figure 1
Reaction scheme showing the one-pot synthesis of the title compound.

2. Structural commentary

In the title compound (Fig. 2), the angle between the planes of the phenyl rings (C12–C17 and C19–C24) of the (4-cyanophenyl)sulfonyl groups is 47.90 (7)°. The furan ring (O1/C7–C10) is inclined at angles of 39.05 (8) and 17.38 (8)° with respect to the C12–C17 and C19–C24 phenyl rings of the (4-cyanophenyl)sulfonyl groups, while it makes a dihedral angle of 20.21 (8)° with the plane of the phenyl ring (C1–C6) attached to the furan ring. The latter phenyl ring makes dihedral angles of 26.28 (7) and 36.40 (7)°, respectively, with the phenyl rings of the (4-cyanophenyl)sulfonyl groups. All geometric parameters are normal and consistent with those of related compounds listed in the Database survey (Section 4).

Figure 2
Molecular structure of the title compound showing the atomic labelling. Displacement ellipsoids are drawn at the 50% probability level.

Intramolecular π–π stacking interactions [Cg1⋯Cg4 = 3.5640 (9) Å; Cg1 and Cg4 are the centroids of the furan (O1/C7–C10) and benzene rings (C19–C24), respectively, of one of the two 4-cyanophenyl)sulfonyl groups, respectively; slippage = 0.793 Å], ensures the stability of the molecular configuration.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal, molecules are linked via C—H⋯O and C—H⋯N hydrogen bonds, forming layers parallel to the (100) plane (Table 1; Fig. 3). These layers are interconnected by C—H⋯π interactions and weak van der Waals interactions, thus ensuring crystal cohesion.

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2ⁱ	0.95	2.56	3.3639 (17)	142
C6—H6⋯O5ⁱⁱ	0.95	2.56	3.3744 (17)	143
C11—H11B⋯N3ⁱⁱⁱ	0.98	2.67	3.616 (2)	163
C16—H16⋯O4^iv	0.95	2.55	3.2115 (18)	127
C21—H21⋯N3ⁱⁱⁱ	0.95	2.54	3.433 (2)	156
C14—H14⋯Cg2^v	0.95	2.85	3.4945 (16)	126
Symmetry codes: (i) x, y+1, z; (ii) ; (iii) ; (iv) ; (v) .

Figure 3
Crystal packing of the title compound along the b axis showing the C—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π and π–π interactions.

Hirshfeld surfaces were generated for the molecule of the title compound using Crystal Explorer 17.5 (Spackman et al., 2021 ). The d_norm mappings was performed in the range −0.3260 to +1.4294 a.u. The C—H⋯O and C—H⋯N interactions are indicated by red areas on the Hirshfeld surfaces (Fig. 4). Fingerprint plots (Fig. 5) reveal that while H⋯H interactions (30.2%) make the largest contributions to surface contacts (Tables 1 and 2), N⋯H/H⋯N (22.3%), C⋯H/H⋯C (17.9%) and O⋯H/H⋯O (15.4%) contacts are also important. Other, less notable interactions are O⋯C/C⋯O (6.0%), C⋯C (5.0%), N⋯N (1.2%), O⋯O (1.1%), N⋯C/C⋯N (0.5%), S⋯H/H⋯S (0.1%) and S⋯O/O⋯S (0.1%).

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

Contact	Distance	Symmetry operation
C25⋯H11C	2.91	−1 + x, y, z
H20⋯H4	2.37	x, −1 + y, z
H11E⋯N2	2.76	2 − x, −y, 1 − z
H20⋯H16	2.44	1 − x, −y, 1 − z
H6⋯O5	2.56	1 − x, 1 − y, 1 − z
H21⋯N3	2.54	1 − x, −y, −z
H8⋯N3	2.73	1 − x, 1 − y, −z
H13⋯H13	2.40	2 − x, 1 − y, 1 − z
H11D⋯H11D	2.02	2 − x, −y, −z

Figure 4
Front (a) and back (b) views of the three-dimensional Hirshfeld surface for the title compound. Some intermolecular C—H⋯O and C—H⋯N interactions are shown.

Figure 5
The two-dimensional fingerprint plots for the title compound showing (a) all interactions, and delineated into (b) H⋯H, (c) N⋯H/H⋯N, (d) C⋯H/H⋯C and (e) O⋯H/H⋯O interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

4. Database survey

Ten related compounds were found as a result of the search for `N-(methanesulfonyl)-N-methylmethanesulfonamide' in the Cambridge Structural Database (CSD, Version 5.42, update of September 2021; Groom et al., 2016 ), viz. PIMGUR (Mammadova et al., 2023), JOBTIF (Kim, 2014 ), CEGMIM (Mughal et al., 2012a ), CEGSUE (Mughal et al., 2012b ), YAXKAL (Taher & Smith, 2012a ), EFASUB (Taher & Smith, 2012b ), OCABUR (Abbassi et al., 2011 ), AYUPUG (Arshad et al., 2011 ), PONZIC (Rizzoli et al., 2009 ) and ROGJON (Li & Song, 2008 ).

In PIMGUR (space group P2₁/n), C—H⋯O hydrogen bonds link adjacent molecules in a three-dimensional network, while π–π stacking interactions [centroid–centroid distance = 3.8745 (9) Å] between the furan and a phenyl ring of one of the two (3-nitrophenyl)sulfonyl groups result in chains parallel to the a axis. In JOBTIF (space group P2₁/n), molecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers. In CEGMIM (space group Pbca), molecules are connected by C—H⋯O interactions into sheets in the ab plane. In the crystal of CEGSUE (space group P $[\overline{1}]$ ), the only directional interactions are very weak C—H⋯π interactions and very weak π–π stacking between parallel methylphenyl rings. In YAXKAL (space group P $[\overline{1}]$ ), molecules associate via pairs of N—H⋯N hydrogen bonds, forming a centrosymmetric eight-membered {⋯HNCN}₂ synthon. In EFASUB (space group C2/c), molecules associate via N—H⋯N and N—H⋯O hydrogen bonds, forming extended hydrogen-bonded sheets that lie parallel to the bc plane. The N—H⋯N hydrogen bonds propagate along the b-axis direction, while the N—H⋯O hydrogen bonds propagate along the c-axis direction. The crystal structure of OCABUR (space group P2₁/c) features C—H⋯O hydrogen bonds. In the crystal structure of AYUPUG (space group P2₁/c), weak C—H⋯O interactions connect the molecules in a zigzag manner along the a-axis direction. In the crystal of PONZIC (space group P $[\overline{1}]$ ), molecules are linked into chains parallel to the a axis by intermolecular C—H⋯O hydrogen bonds and π–π stacking interactions. In ROGJON (space group Pbca), the crystal structure features weak intermolecular N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds and π–π interactions.

5. Synthesis and crystallization

p-Cyanobenzenesulphonyl chloride (2.33 g, 0.0115 mol) was added gradually to a solution of 2-(5-methyl-2-furyl)aniline (1.00 g, 0.00577 mol) in pyridine (7 mL) under stirring and cooling in an ice–water bath. The mixture was stirred for 7 h at r.t. and after completion of the reaction [thin-layer chromatography (TLC) monitoring; sorbfil, hexane/ethyl acetate 4:1], the mixture was poured into hydrochloric acid (6 M, 90 mL). The separated oil was washed with water until its crystallization. The obtained crystals were filtered off, dried, and recrystallized from an ethanol/dimethylformamide (DMF) mixture to give the target disulfonamide as a colourless solid. Single crystals were obtained by slow crystallization from an EtOH/DMF mixture (yield 64%, 1.86 g; m.p. 507–508 K). IR (KBr), ν (cm⁻¹): 1156 (ν_s SO₂), 1329 (ν_as SO₂), 2237 (CN). ¹H NMR (600.2 MHz, DMSO-d₆) (J, Hz): δ 8.08 (d, J = 8.6 Hz, 4H), 7.90 (d, J = 8.6 Hz, 4H), 7.72 (dd, J = 8.1, 1.5 Hz, 1H), 7.56 (dt, J = 8.6, 1.5 Hz, 1H), 7.36 (dt, J = 8.1, 1.5 Hz, 1H), 7.04 (dd, J = 8.1, 1.5 Hz, 1H), 6.61 (d, J = 3.5 Hz, 1H), 5.93 (br.d, J = 3.5 Hz, 1H), 1.96 (s, 3H); ¹³C{¹H} NMR (150.9 MHz, DMSO-d₆): δ 153.2, 147.9 (2C), 142.9, 134.0 (4C), 133.7, 132.2, 132.0, 129.6 (4C), 128.8, 128.7, 128.6, 117.9 (2C), 117.4 (2C), 112.0, 108.6, 13.4; MS (ESI) m/z: [M + H]⁺ 504. Elemental analysis calculated (%) for C₂₅H₁₇N₃O₅S₂ %: C 59.63, H 3.40, N 8.34, S 12.74; found: C 60.00, H 3.27, N 8.56, S 13.03.

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 0.98 Å) and included as riding contributions with isotropic displacement parameters fixed at 1.2U_eq(C) (1.5 for methyl groups). The hydrogen atoms of the methyl group containing the C11 atom were disordered over two positions with equal occupancies.

Table 3
Experimental details

Crystal data
Chemical formula	C₂₅H₁₇N₃O₅S₂
M_r	503.53
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	7.4542 (1), 9.5111 (2), 16.4378 (3)
α, β, γ (°)	88.838 (4), 81.644 (1), 81.414 (1)
V (Å³)	1140.11 (4)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	2.50
Crystal size (mm)	0.29 × 0.22 × 0.15

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.481, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	29936, 4841, 4675
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.095, 1.08
No. of reflections	4841
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.60
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: 2282070

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989023006254/tx2071sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023006254/tx2071Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989023006254/tx2071Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO 1.171.41.117a (Rigaku OD, 2021); cell refinement: CrysAlis PRO 1.171.41.117a (Rigaku OD, 2021); data reduction: CrysAlis PRO 1.171.41.117a (Rigaku OD, 2021); program(s) used to solve structure: SHELXL2016/6 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

4-Cyano-N-[(4-cyanophenyl)sulfonyl]-N-[2-(5-methylfuran-2-yl)phenyl]benzenesulfonamide top

Crystal data top

C₂₅H₁₇N₃O₅S₂	Z = 2
M_r = 503.53	F(000) = 520
Triclinic, P1	D_x = 1.467 Mg m⁻³
a = 7.4542 (1) Å	Cu Kα radiation, λ = 1.54184 Å
b = 9.5111 (2) Å	Cell parameters from 21520 reflections
c = 16.4378 (3) Å	θ = 2.7–77.6°
α = 88.838 (4)°	µ = 2.50 mm⁻¹
β = 81.644 (1)°	T = 100 K
γ = 81.414 (1)°	Prism, colourless
V = 1140.11 (4) Å³	0.29 × 0.22 × 0.15 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	4841 independent reflections
Radiation source: micro-focus sealed X-ray tube	4675 reflections with I > 2σ(I)
Detector resolution: 0 pixels mm^-1	R_int = 0.051
φ and ω scans	θ_max = 77.9°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2021)	h = −8→9
T_min = 0.481, T_max = 1.000	k = −12→12
29936 measured reflections	l = −20→20

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0547P)² + 0.4479P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
4841 reflections	Δρ_max = 0.76 e Å⁻³
316 parameters	Δρ_min = −0.60 e Å⁻³

Special details top

Experimental. CrysAlisPro 1.171.41.117a (Rigaku OD, 2021) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.87131 (4)	0.20718 (3)	0.37143 (2)	0.01631 (10)
S2	0.47488 (4)	0.28580 (3)	0.36436 (2)	0.01531 (10)
O1	0.86050 (14)	0.27336 (10)	0.19206 (6)	0.0209 (2)
O2	0.85236 (14)	0.07100 (10)	0.34200 (6)	0.0224 (2)
O3	1.02688 (13)	0.27486 (11)	0.34195 (6)	0.0214 (2)
O4	0.47897 (13)	0.15314 (11)	0.40679 (6)	0.0207 (2)
O5	0.35697 (13)	0.40880 (11)	0.39862 (6)	0.0208 (2)
N1	0.68945 (15)	0.32549 (12)	0.35205 (7)	0.0154 (2)
N2	0.7640 (2)	0.22944 (17)	0.80753 (9)	0.0376 (3)
N3	0.3238 (2)	0.18901 (15)	−0.04558 (8)	0.0301 (3)
C1	0.71285 (17)	0.47104 (14)	0.33138 (8)	0.0166 (3)
C2	0.76977 (18)	0.51151 (15)	0.25007 (9)	0.0190 (3)
C3	0.7802 (2)	0.65682 (16)	0.23618 (10)	0.0244 (3)
H3	0.819030	0.687961	0.182071	0.029*
C4	0.7355 (2)	0.75524 (15)	0.29928 (10)	0.0261 (3)
H4	0.742788	0.852707	0.287872	0.031*
C5	0.67996 (19)	0.71301 (16)	0.37940 (10)	0.0238 (3)
H5	0.649904	0.780898	0.422687	0.029*
C6	0.66904 (18)	0.57071 (15)	0.39520 (9)	0.0196 (3)
H6	0.631585	0.540682	0.449686	0.024*
C7	0.81504 (19)	0.41619 (15)	0.17921 (9)	0.0201 (3)
C8	0.8215 (2)	0.44092 (18)	0.09722 (10)	0.0294 (3)
H8	0.796625	0.530602	0.071431	0.035*
C9	0.8728 (2)	0.30600 (19)	0.05734 (9)	0.0308 (3)
H9	0.888002	0.288669	−0.000144	0.037*
C10	0.8957 (2)	0.20782 (17)	0.11670 (9)	0.0242 (3)
C11	0.9513 (2)	0.05141 (18)	0.11806 (10)	0.0320 (4)
H11A	0.951112	0.019245	0.175088	0.048*	0.5
H11B	0.864718	0.004742	0.092582	0.048*	0.5
H11C	1.074697	0.026944	0.087412	0.048*	0.5
H11D	0.975906	0.014709	0.061633	0.048*	0.5
H11E	1.062300	0.029212	0.144140	0.048*	0.5
H11F	0.852321	0.007010	0.149309	0.048*	0.5
C12	0.85015 (18)	0.20354 (14)	0.47982 (8)	0.0176 (3)
C13	0.91148 (19)	0.31300 (14)	0.51825 (9)	0.0197 (3)
H13	0.967389	0.383552	0.486494	0.024*
C14	0.88981 (19)	0.31752 (15)	0.60333 (9)	0.0208 (3)
H14	0.928202	0.392513	0.630580	0.025*
C15	0.81124 (19)	0.21113 (15)	0.64858 (9)	0.0206 (3)
C16	0.75614 (19)	0.09909 (15)	0.60938 (9)	0.0225 (3)
H16	0.706667	0.025466	0.640954	0.027*
C17	0.77392 (19)	0.09578 (15)	0.52430 (9)	0.0204 (3)
H17	0.734758	0.021287	0.496928	0.025*
C18	0.7855 (2)	0.21874 (17)	0.73718 (10)	0.0265 (3)
C19	0.43219 (17)	0.26331 (14)	0.26310 (8)	0.0161 (3)
C20	0.47823 (19)	0.12911 (15)	0.22776 (9)	0.0201 (3)
H20	0.531585	0.051367	0.257755	0.024*
C21	0.4455 (2)	0.10992 (15)	0.14829 (9)	0.0223 (3)
H21	0.473180	0.018398	0.123514	0.027*
C22	0.37117 (19)	0.22685 (16)	0.10504 (8)	0.0203 (3)
C23	0.3246 (2)	0.36132 (16)	0.14114 (9)	0.0234 (3)
H23	0.272363	0.439559	0.111171	0.028*
C24	0.3553 (2)	0.37968 (15)	0.22120 (9)	0.0212 (3)
H24	0.324252	0.470377	0.246872	0.025*
C25	0.3437 (2)	0.20666 (16)	0.02113 (9)	0.0242 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01287 (16)	0.01633 (16)	0.01966 (17)	−0.00131 (11)	−0.00276 (12)	−0.00148 (12)
S2	0.01201 (16)	0.01925 (17)	0.01516 (16)	−0.00367 (11)	−0.00191 (11)	−0.00204 (12)
O1	0.0234 (5)	0.0214 (5)	0.0178 (5)	−0.0057 (4)	0.0000 (4)	−0.0028 (4)
O2	0.0235 (5)	0.0175 (5)	0.0260 (5)	−0.0012 (4)	−0.0044 (4)	−0.0049 (4)
O3	0.0134 (5)	0.0265 (5)	0.0241 (5)	−0.0030 (4)	−0.0020 (4)	0.0003 (4)
O4	0.0192 (5)	0.0256 (5)	0.0193 (5)	−0.0086 (4)	−0.0045 (4)	0.0028 (4)
O5	0.0143 (4)	0.0260 (5)	0.0215 (5)	−0.0012 (4)	−0.0015 (4)	−0.0081 (4)
N1	0.0119 (5)	0.0163 (5)	0.0184 (5)	−0.0034 (4)	−0.0024 (4)	−0.0002 (4)
N2	0.0433 (9)	0.0437 (8)	0.0247 (7)	−0.0043 (7)	−0.0037 (6)	0.0032 (6)
N3	0.0361 (7)	0.0327 (7)	0.0207 (6)	0.0003 (6)	−0.0065 (5)	−0.0033 (5)
C1	0.0133 (6)	0.0157 (6)	0.0214 (6)	−0.0023 (4)	−0.0044 (5)	−0.0007 (5)
C2	0.0155 (6)	0.0206 (6)	0.0220 (7)	−0.0040 (5)	−0.0055 (5)	0.0013 (5)
C3	0.0247 (7)	0.0229 (7)	0.0279 (7)	−0.0066 (5)	−0.0095 (6)	0.0056 (6)
C4	0.0239 (7)	0.0174 (6)	0.0393 (9)	−0.0028 (5)	−0.0129 (6)	0.0026 (6)
C5	0.0187 (7)	0.0204 (7)	0.0333 (8)	−0.0010 (5)	−0.0080 (6)	−0.0072 (6)
C6	0.0148 (6)	0.0214 (7)	0.0231 (7)	−0.0017 (5)	−0.0049 (5)	−0.0037 (5)
C7	0.0170 (6)	0.0225 (7)	0.0211 (7)	−0.0046 (5)	−0.0021 (5)	0.0018 (5)
C8	0.0334 (8)	0.0322 (8)	0.0208 (7)	−0.0011 (6)	−0.0024 (6)	0.0030 (6)
C9	0.0332 (8)	0.0394 (9)	0.0178 (7)	−0.0019 (7)	−0.0002 (6)	−0.0035 (6)
C10	0.0222 (7)	0.0302 (8)	0.0195 (7)	−0.0065 (6)	0.0029 (5)	−0.0076 (6)
C11	0.0368 (9)	0.0291 (8)	0.0276 (8)	−0.0056 (6)	0.0054 (7)	−0.0087 (6)
C12	0.0139 (6)	0.0173 (6)	0.0218 (6)	−0.0001 (5)	−0.0056 (5)	0.0002 (5)
C13	0.0186 (6)	0.0180 (6)	0.0236 (7)	−0.0041 (5)	−0.0055 (5)	0.0016 (5)
C14	0.0190 (7)	0.0196 (6)	0.0244 (7)	−0.0010 (5)	−0.0071 (5)	−0.0005 (5)
C15	0.0159 (6)	0.0225 (7)	0.0227 (7)	0.0009 (5)	−0.0047 (5)	0.0025 (5)
C16	0.0184 (7)	0.0223 (7)	0.0276 (7)	−0.0042 (5)	−0.0055 (5)	0.0056 (5)
C17	0.0177 (6)	0.0180 (6)	0.0269 (7)	−0.0034 (5)	−0.0072 (5)	0.0012 (5)
C18	0.0242 (7)	0.0271 (7)	0.0279 (8)	−0.0023 (6)	−0.0050 (6)	0.0039 (6)
C19	0.0116 (6)	0.0210 (6)	0.0164 (6)	−0.0038 (5)	−0.0022 (5)	−0.0020 (5)
C20	0.0202 (7)	0.0196 (6)	0.0195 (6)	0.0001 (5)	−0.0027 (5)	−0.0007 (5)
C21	0.0243 (7)	0.0214 (7)	0.0205 (7)	−0.0006 (5)	−0.0028 (5)	−0.0055 (5)
C22	0.0167 (6)	0.0277 (7)	0.0169 (6)	−0.0042 (5)	−0.0026 (5)	−0.0022 (5)
C23	0.0257 (7)	0.0223 (7)	0.0224 (7)	−0.0004 (5)	−0.0078 (5)	0.0012 (5)
C24	0.0224 (7)	0.0197 (6)	0.0217 (7)	−0.0014 (5)	−0.0058 (5)	−0.0029 (5)
C25	0.0239 (7)	0.0272 (7)	0.0206 (7)	−0.0008 (6)	−0.0027 (5)	−0.0022 (6)

Geometric parameters (Å, º) top

S1—O2	1.4253 (10)	C10—C11	1.484 (2)
S1—O3	1.4287 (10)	C11—H11A	0.9800
S1—N1	1.6914 (11)	C11—H11B	0.9800
S1—C12	1.7657 (14)	C11—H11C	0.9800
S2—O5	1.4262 (10)	C11—H11D	0.9800
S2—O4	1.4277 (10)	C11—H11E	0.9800
S2—N1	1.6807 (11)	C11—H11F	0.9800
S2—C19	1.7625 (13)	C12—C17	1.3895 (19)
O1—C7	1.3699 (17)	C12—C13	1.3946 (19)
O1—C10	1.3711 (17)	C13—C14	1.385 (2)
N1—C1	1.4484 (16)	C13—H13	0.9500
N2—C18	1.148 (2)	C14—C15	1.393 (2)
N3—C25	1.147 (2)	C14—H14	0.9500
C1—C6	1.3979 (19)	C15—C16	1.398 (2)
C1—C2	1.4062 (19)	C15—C18	1.443 (2)
C2—C3	1.408 (2)	C16—C17	1.386 (2)
C2—C7	1.459 (2)	C16—H16	0.9500
C3—C4	1.382 (2)	C17—H17	0.9500
C3—H3	0.9500	C19—C24	1.3863 (19)
C4—C5	1.392 (2)	C19—C20	1.3877 (19)
C4—H4	0.9500	C20—C21	1.384 (2)
C5—C6	1.385 (2)	C20—H20	0.9500
C5—H5	0.9500	C21—C22	1.396 (2)
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.359 (2)	C22—C23	1.395 (2)
C8—C9	1.427 (2)	C22—C25	1.4442 (19)
C8—H8	0.9500	C23—C24	1.387 (2)
C9—C10	1.348 (2)	C23—H23	0.9500
C9—H9	0.9500	C24—H24	0.9500

O2—S1—O3	121.57 (6)	C10—C11—H11B	109.5
O2—S1—N1	108.74 (6)	H11A—C11—H11B	109.5
O3—S1—N1	104.43 (6)	C10—C11—H11C	109.5
O2—S1—C12	109.39 (6)	H11A—C11—H11C	109.5
O3—S1—C12	107.41 (6)	H11B—C11—H11C	109.5
N1—S1—C12	103.85 (6)	H11D—C11—H11E	109.5
O5—S2—O4	120.18 (6)	H11D—C11—H11F	109.5
O5—S2—N1	106.78 (6)	H11E—C11—H11F	109.5
O4—S2—N1	106.87 (6)	C17—C12—C13	121.92 (13)
O5—S2—C19	108.34 (6)	C17—C12—S1	120.72 (11)
O4—S2—C19	109.55 (6)	C13—C12—S1	117.36 (11)
N1—S2—C19	103.90 (6)	C14—C13—C12	119.13 (13)
C7—O1—C10	107.60 (11)	C14—C13—H13	120.4
C1—N1—S2	117.35 (9)	C12—C13—H13	120.4
C1—N1—S1	119.89 (9)	C13—C14—C15	119.42 (13)
S2—N1—S1	122.51 (7)	C13—C14—H14	120.3
C6—C1—C2	121.38 (13)	C15—C14—H14	120.3
C6—C1—N1	117.08 (12)	C14—C15—C16	120.97 (14)
C2—C1—N1	121.49 (12)	C14—C15—C18	118.91 (14)
C1—C2—C3	116.84 (13)	C16—C15—C18	120.11 (13)
C1—C2—C7	125.48 (12)	C17—C16—C15	119.79 (13)
C3—C2—C7	117.67 (13)	C17—C16—H16	120.1
C4—C3—C2	121.64 (14)	C15—C16—H16	120.1
C4—C3—H3	119.2	C16—C17—C12	118.71 (13)
C2—C3—H3	119.2	C16—C17—H17	120.6
C3—C4—C5	120.66 (14)	C12—C17—H17	120.6
C3—C4—H4	119.7	N2—C18—C15	177.81 (17)
C5—C4—H4	119.7	C24—C19—C20	122.18 (13)
C6—C5—C4	119.13 (14)	C24—C19—S2	119.24 (10)
C6—C5—H5	120.4	C20—C19—S2	118.57 (10)
C4—C5—H5	120.4	C21—C20—C19	119.19 (13)
C5—C6—C1	120.35 (14)	C21—C20—H20	120.4
C5—C6—H6	119.8	C19—C20—H20	120.4
C1—C6—H6	119.8	C20—C21—C22	119.10 (13)
C8—C7—O1	109.22 (13)	C20—C21—H21	120.5
C8—C7—C2	131.86 (14)	C22—C21—H21	120.5
O1—C7—C2	118.92 (12)	C23—C22—C21	121.32 (13)
C7—C8—C9	106.68 (14)	C23—C22—C25	120.03 (13)
C7—C8—H8	126.7	C21—C22—C25	118.65 (13)
C9—C8—H8	126.7	C24—C23—C22	119.37 (13)
C10—C9—C8	107.01 (13)	C24—C23—H23	120.3
C10—C9—H9	126.5	C22—C23—H23	120.3
C8—C9—H9	126.5	C19—C24—C23	118.81 (13)
C9—C10—O1	109.49 (13)	C19—C24—H24	120.6
C9—C10—C11	135.03 (14)	C23—C24—H24	120.6
O1—C10—C11	115.47 (13)	N3—C25—C22	179.03 (16)
C10—C11—H11A	109.5

O5—S2—N1—C1	−33.62 (11)	C8—C9—C10—O1	0.37 (18)
O4—S2—N1—C1	−163.42 (10)	C8—C9—C10—C11	−178.47 (17)
C19—S2—N1—C1	80.78 (11)	C7—O1—C10—C9	−0.20 (16)
O5—S2—N1—S1	140.59 (8)	C7—O1—C10—C11	178.89 (13)
O4—S2—N1—S1	10.79 (9)	O2—S1—C12—C17	−16.82 (13)
C19—S2—N1—S1	−105.01 (8)	O3—S1—C12—C17	−150.62 (11)
O2—S1—N1—C1	−145.42 (10)	N1—S1—C12—C17	99.12 (12)
O3—S1—N1—C1	−14.26 (11)	O2—S1—C12—C13	163.63 (10)
C12—S1—N1—C1	98.17 (11)	O3—S1—C12—C13	29.83 (12)
O2—S1—N1—S2	40.51 (9)	N1—S1—C12—C13	−80.43 (11)
O3—S1—N1—S2	171.67 (7)	C17—C12—C13—C14	−2.4 (2)
C12—S1—N1—S2	−75.89 (9)	S1—C12—C13—C14	177.14 (10)
S2—N1—C1—C6	77.49 (14)	C12—C13—C14—C15	1.5 (2)
S1—N1—C1—C6	−96.87 (13)	C13—C14—C15—C16	0.8 (2)
S2—N1—C1—C2	−99.91 (13)	C13—C14—C15—C18	−178.59 (13)
S1—N1—C1—C2	85.72 (14)	C14—C15—C16—C17	−2.2 (2)
C6—C1—C2—C3	−0.1 (2)	C18—C15—C16—C17	177.20 (13)
N1—C1—C2—C3	177.24 (12)	C15—C16—C17—C12	1.3 (2)
C6—C1—C2—C7	−178.78 (13)	C13—C12—C17—C16	1.0 (2)
N1—C1—C2—C7	−1.5 (2)	S1—C12—C17—C16	−178.51 (10)
C1—C2—C3—C4	−0.4 (2)	O5—S2—C19—C24	23.09 (13)
C7—C2—C3—C4	178.39 (13)	O4—S2—C19—C24	155.90 (11)
C2—C3—C4—C5	0.6 (2)	N1—S2—C19—C24	−90.20 (12)
C3—C4—C5—C6	−0.3 (2)	O5—S2—C19—C20	−157.37 (11)
C4—C5—C6—C1	−0.2 (2)	O4—S2—C19—C20	−24.55 (13)
C2—C1—C6—C5	0.4 (2)	N1—S2—C19—C20	89.35 (11)
N1—C1—C6—C5	−177.05 (12)	C24—C19—C20—C21	−0.5 (2)
C10—O1—C7—C8	−0.07 (16)	S2—C19—C20—C21	180.00 (11)
C10—O1—C7—C2	179.71 (12)	C19—C20—C21—C22	1.6 (2)
C1—C2—C7—C8	158.84 (16)	C20—C21—C22—C23	−1.9 (2)
C3—C2—C7—C8	−19.9 (2)	C20—C21—C22—C25	177.80 (13)
C1—C2—C7—O1	−20.9 (2)	C21—C22—C23—C24	1.0 (2)
C3—C2—C7—O1	160.40 (12)	C25—C22—C23—C24	−178.67 (13)
O1—C7—C8—C9	0.29 (17)	C20—C19—C24—C23	−0.4 (2)
C2—C7—C8—C9	−179.45 (15)	S2—C19—C24—C23	179.11 (11)
C7—C8—C9—C10	−0.40 (19)	C22—C23—C24—C19	0.2 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.95	2.56	3.3639 (17)	142
C6—H6···O5ⁱⁱ	0.95	2.56	3.3744 (17)	143
C11—H11B···N3ⁱⁱⁱ	0.98	2.67	3.616 (2)	163
C13—H13···O3	0.95	2.56	2.9146 (18)	102
C16—H16···O4^iv	0.95	2.55	3.2115 (18)	127
C21—H21···N3ⁱⁱⁱ	0.95	2.54	3.433 (2)	156
C24—H24···O5	0.95	2.59	2.9371 (18)	102
C14—H14···Cg2^v	0.95	2.85	3.4945 (16)	126

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

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

Contact	Distance	Symmetry operation
C25···H11C	2.91	-1 + x, y, z
H20···H4	2.37	x, -1 + y, z
H11E···N2	2.76	2 - x, -y, 1 - z
H20···H16	2.44	1 - x, -y, 1 - z
H6···O5	2.56	1 - x, 1 - y, 1 - z
H21···N3	2.54	1 - x, -y, -z
H8···N3	2.73	1 - x, 1 - y, -z
H13···H13	2.40	2 - x, 1 - y, 1 - z
H11D···H11D	2.02	2 - x, -y, -z

Acknowledgements

The authors' contributions are as follows. Conceptualization, MA and AB; synthesis, EDY and GMB; X-ray analysis, GZM, VNK, MA, and STÇ; writing (review and editing of the manuscript) MA and AB; funding acquisition, GZM; supervision, MA and AB.

Funding information

GMZ thanks Baku State University for financial support.

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