Crystal structure and Hirshfeld surface analysis of N-[2-(5-methyl­furan-2-yl)phen­yl]-3-nitro-N-[(3-nitro­phen­yl)sulfon­yl]benzene­sulfonamide

Mammadova, G.Z.; Annadurdyyeva, S.; Burkin, G.M.; Khrustalev, V.N.; Akkurt, M.; Yıldırım, S. Ö.; Bhattarai, A.

doi:10.1107/S2056989023003523

research communications

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 79| Part 5| May 2023| Pages 499-503

https://doi.org/10.1107/S2056989023003523

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Crystal structure and Hirshfeld surface analysis of N-[2-(5-methylfuran-2-yl)phenyl]-3-nitro-N-[(3-nitrophenyl)sulfonyl]benzenesulfonamide

Gunay Z. Mammadova,^a Selbi Annadurdyyeva,^b Gleb M. Burkin,^b Victor N. Khrustalev,^b,^c Mehmet Akkurt,^d Sema Öztürk Yıldırım ^e,^d and Ajaya Bhattarai ^f ^*

^aExcellence Center, 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, ^eDepartment of Physics, Faculty of Science, Eskisehir Technical University, Yunus Emre Campus, 26470 Eskisehir, Türkiye, and ^fDepartment of Chemistry, M.M.A.M.C. (Tribhuvan University), Biratnagar, Nepal
^*Correspondence e-mail: ajaya.bhattarai@mmamc.tu.edu.np

Edited by B. Therrien, University of Neuchâtel, Switzerland (Received 13 April 2023; accepted 18 April 2023; online 25 April 2023)

In the title compound, C₂₃H₁₇N₃O₉S₂, C—H⋯O hydrogen bonds link adjacent molecules in a three-dimensional network, while π–π stacking interactions, with centroid–centroid distances of 3.8745 (9) Å, between the furan and an arene ring of one of the two (3-nitrophenyl)sulfonyl groups, result in chains parallel to the a axis. The Hirshfeld surface analysis indicates that O⋯H/H⋯O (40.1%), H⋯H (27.5%) and C⋯H/H⋯C (12.4%) interactions are the most significant contributors to the crystal packing.

Keywords: crystal structure; sulfonamides; hydrogen bonds; π–π stacking interactions; Hirshfeld surface analysis.

CCDC reference: 2257159

1. Chemical context

The synthesis of sulfonamides has been given considerable attention in the literature. A large number of reports are based on various chemical and physical properties, methods of synthesis and application of sulfonamides (Safavora et al., 2019 ). The electronic and structural properties of the sulfonamide moiety make it a bioisostere of such compounds as urea, thiourea, carbamates and sulfamides (Reitz et al., 2009 ; Abdelhamid et al., 2011 ; Khalilov et al., 2021 ). Linear and cyclic compounds containing sulfonamide fragments have a wide range of biological activity – they possess antibacterial properties (Yun et al., 2012 ; Nadirova et al., 2021 ), show diuretic activity (Logemann et al., 1959 ; DeStevens et al., 1959 ), are active against seizures (Thiry et al., 2008 ) and inhibit various enzymes like human leukocyte elastase and cathepsin G, a HIV-1 protease (Supuran et al., 2003 ). Sulfonamides are also used as fungicidal (Chohan et al., 2006 , 2010 ) and insecticidal mixtures. The most widely used furan-substituted sulfonylamide is Furosemide, a loop diuretic medication used to treat fluid build-up due to heart failure, kidney disease or liver scarring. Typically, furan-substituted monosulfamides are obtained by treatment of the amines with the corresponding sulfonyl chlorides (Pilipenko et al., 2012 ; Butin et al., 2006 ; Naghiyev et al., 2020 ). It turned out unexpectedly that the interaction of 2-(α-furyl)aniline with sulfochloride containing the electron-withdrawing 3-nitrophenyl group under the same conditions gives a double sulfarylation product (Fig. 1), which is possible only with the use of strong bases (Bartsch et al., 1977 ; Li et al., 2022 ). The obtained product can serve as a compound for studying furan fragment-opening (Pilipenko et al., 2012; Butin et al., 2006) or the Diels–Alder reactions of furans (Borisova et al., 2018a ,b ; Krishna et al., 2022 ; Zubkov et al., 2007 ) and for studying biological activity. On the other hand, intermolecular noncovalent interactions organize the molecular aggregates, catalytic intermediates, etc., which play a critical role in the functional properties of heterocyclic compounds (Gurbanov et al., 2020a ,b , 2022 ; Ma et al., 2021 ; Mahmoudi, et al., 2017a ,b ; Mahmudov et al., 2011 , 2022 ).

Figure 1
One-pot synthesis of N-[2-(5-methylfuran-2-yl)phenyl]-3-nitro-N-[(3-nitrophenyl)sulfonyl]benzenesulfonamide.

2. Structural commentary

In the title compound (Fig. 2), the angle between the planes of the arene rings (C12–C17 and C18–C23) of the (3-nitrophenyl)sulfonyl groups are 40.87 (7)°. The furan ring (O1/C7–C10) is inclined at angles of 51.04 (8) and 12.78 (8)° with respect to the arene rings (C12–C17 and C18–C23) of the (3-nitrophenyl)sulfonyl groups, while it makes a dihedral angle of 20.77 (8)° with the plane of the arene ring (C1–C6) attached to the furan ring. The arene ring attached to the furan ring makes dihedral angles of 33.19 (7) and 17.84 (7)°, respectively, with the arene rings of the 3-nitrophenyl)sulfonyl groups. The geometric properties of the title compound are normal and consistent with those of related compounds listed in the Database survey (Section 4).

Figure 2
The molecular structure of the title compound, showing the atom labelling and with displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal of the title compound, molecules are linked by intermolecular C—H⋯O hydrogen bonds forming the three-dimensional network (Tables 1 and 2), while π–π stacking interactions {Cg1⋯Cg4^iv = 3.8745 (9) Å [symmetry code: (iv) x + 1, y, z], where Cg1 and Cg4 are the centroids of the furan ring (atoms O1/C7–C10) and the arene ring (atoms C18–C23) of one of the two (3-nitrophenyl)sulfonyl groups; slippage = 1.389 Å} form chains along the a axis (Figs. 3 and 4).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O4ⁱ	0.95	2.31	3.226 (2)	161
C16—H16⋯O2ⁱⁱ	0.95	2.53	3.0874 (18)	118
C19—H19⋯O4ⁱⁱⁱ	0.95	2.58	2.981 (2)	106
Symmetry codes: (i) $[-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) ; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Table 2
Summary of short interatomic contacts (Å).

Contact	Distance	Symmetry operation
N2⋯O3	3.03	−x + 2, −y + 1, −z + 1
H19⋯H15	2.58	−x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{3\over 2}]$
H16⋯O2	2.53	−x + 1, −y + 1, −z + 1
O5⋯H17	2.62	x + 1, y, z
O4⋯H3	2.31	−x + $[{5\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{3\over 2}]$
H4⋯H8	2.46	x + $[{1\over 2}]$ , −y + $[{3\over 2}]$ , z + $[{1\over 2}]$
H9⋯O8	2.67	−x + 1, −y + 2, −z + 1

Figure 3
The crystal packing along the a axis, showing the C—H⋯O hydrogen-bond network and the π–π stacking interactions.

Figure 4
The crystal packing diagram along the b axis, showing the intermolecular C—H⋯O hydrogen bonds.

Hirshfeld surfaces were generated for the title molecule using CrystalExplorer17 (Spackman et al., 2021 ). The d_norm mappings was performed in the range from −0.3170 to +1.1777 a.u. The C—H⋯O interactions are indicated by red areas on the Hirshfeld surfaces [Figs. 5(a) and 5(b)]. Fingerprint plots (Fig. 6) reveal that, while O⋯H/H⋯O interactions (40.1%) make the largest contributions to the surface contacts (Tables 1 and 2), H⋯H (27.5%) and C⋯H/H⋯C (12.4%) contacts are also important. Other less notable linkages are O⋯C/C⋯O (6.0%), O⋯O (5.7%), C⋯C (4.9%), O⋯N/N⋯O (2.0%), N⋯H/H⋯N (1.2%), S⋯C/C⋯S (0.1%) and S⋯O/O⋯S (0.1%).

Figure 5
(a) Front and (b) back views of the three-dimensional Hirshfeld surface, with some intermolecular C—H⋯O interactions shown.

Figure 6
The 2D fingerprint plots for the title molecule, showing (a) all interactions, and delineated into (b) O⋯H/H⋯O, (c) H⋯H and (d) C⋯H/H⋯C 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

The nine related compounds found as a result of the search for `N-(methanesulfonyl)-N-methyl methanesulfonamide' in the Cambridge Structural Database (CSD, Version 5.42, update of September 2021; Groom et al., 2016 ) are for N-(2-formylphenyl)-4-methyl-N-[(4-methylphenyl)sulfonyl]benzenesulfonamide, i.e. CSD refcodes JOBTIF (Kim, 2014 ), CEGMIM (Mughal et al., 2012a ), YAXKAL (Taher & Smith, 2012a ), OCABUR (Abbassi et al., 2011 ), CEGSUE (Mughal et al., 2012b ), EFASUB (Taher & Smith, 2012b ), PONZIC (Rizzoli et al., 2009 ), AYUPUG (Arshad et al., 2011 ) and ROGJON (Li & Song, 2008 ).

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 YAXKAL (space group P $[\overline{1}]$ ), molecules associate via pairs of N—H⋯N hydrogen bonds, forming a centrosymmetric eight-membered {⋯HNCN}₂ synthon. The crystal structure of OCABUR (space group P2₁/c) is stabilized by intermolecular C—H⋯O hydrogen bonds. In the crystal of CEGSUE (space group P $[\overline{1}]$ ), the only possible directional interactions are very weak C—H⋯π interactions and very weak π–π stacking between parallel methylphenyl rings. 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. In the crystal packing 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 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. In ROGJON (space group Pbca), the crystal sructure exhibits weak intermolecular N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds and π–π interactions.

5. Synthesis and crystallization

To a solution of 2-(5-methylfuran-2-yl)aniline (1.09 g, 0.0058 mol) in 7 ml of pyridine under stirring and cooling in an ice-water bath, m-nitrobenzenesulfonyl chloride (2.59 g, 0.0117 mol) was added gradually. The mixture was stirred for 7 h and after completion of the reaction [thin-layer chromatography (TLC) monitoring], the mixture was poured into 90 ml of 6 M hydrochloric acid. The oil which separated was washed with water until it crystallized. The crystals were filtered off, dried and crystallized from an ethanol/dimethylformamide (DMF) mixture to give the target disulfonamide as a yellow solid. A single crystal of N-[2-(5-methylfuran-2-yl)phenyl]-3-nitro-N-[(3-nitrophenyl)sulfonyl]benzenesulfonamide was obtained by slow crystallization from an ethanol/DMF mixture (yield 62%, 1.94 g; m.p. 467–469 K). IR (KBr), ν (cm⁻¹): 1176 (ν_s SO₂), 1352 (br, ν_as SO₂, ν_s NO₂), 1530 (ν_as NO₂). ¹H NMR (600.2 MHz, DMSO-d₆) (J, Hz): δ 8.60 (dd, J = 8.1, 1.5 Hz, 2H), 8.36 (t, J = 1.5 Hz, 2H), 8.25 (d, J = 8.1 Hz, 2H), 7.94 (t, J = 8.1 Hz, 2H), 7.75 (dd, J = 8.1, 1.5 Hz, 1H), 7.59 (dt, J = 8.1, 1.0 Hz, 1H), 7.38 (dt, J = 8.1, 1.0 Hz, 1H), 7.12 (d, J = 8.1 Hz, 1H), 6.60 (d, J = 3.5 Hz, 1H), 5.81 (d, J = 3.5 Hz, 1H), 1.86 (s, 3H). ¹³C{¹H} NMR (150.9 MHz, DMSO-d₆): δ 153.2 (2C), 148.2, 147.9, 140.4, 134.9, 133.8, 132.2, 132.1, 132.0, 129.7, 129.0, 128.8, 123.4, 112.0, 108.5, 13.3; MS (ESI) m/z: [M + H]⁺ 544.37. Analysis calculated (%) for C₂₃H₁₇N₃O₉S₂: C 50.82, H 3.15, N 7.73, S 11.80; found: C 51.07, H 3.17, N 7.56, S 12.03.

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 = 0.95–0.98 Å) and included as riding contributions with isotropic displacement parameters fixed at 1.2U_eq(C) (1.5 for the methyl groups).

Table 3
Experimental details

Crystal data
Chemical formula	C₂₃H₁₇N₃O₉S₂
M_r	543.52
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	8.10683 (6), 19.20010 (15), 14.49754 (10)
β (°)	90.8104 (7)
V (Å³)	2256.35 (3)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	2.71
Crystal size (mm)	0.33 × 0.12 × 0.11

Data collection
Diffractometer	Rigaku XtaLAB Synergy Dualflex HyPix
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ )
T_min, T_max	0.411, 0.725
No. of measured, independent and observed [I > 2σ(I)] reflections	30531, 4812, 4547
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.100, 1.07
No. of reflections	4812
No. of parameters	335
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.50
Computer programs: CrysAlis PRO (Rigaku OD, 2021 $[Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ), SHELXL2016 (Sheldrick, 2015a ), SHELXL2016 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2257159

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989023003523/tx2067sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023003523/tx2067Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989023003523/tx2067Isup3.cml

checkCIF report

Computing details top

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

N-[2-(5-Methylfuran-2-yl)phenyl]-3-nitro-N-[(3-nitrophenyl)sulfonyl]benzenesulfonamide top

Crystal data top

C₂₃H₁₇N₃O₉S₂	F(000) = 1120
M_r = 543.52	D_x = 1.600 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 8.10683 (6) Å	Cell parameters from 20996 reflections
b = 19.20010 (15) Å	θ = 3.8–77.7°
c = 14.49754 (10) Å	µ = 2.71 mm⁻¹
β = 90.8104 (7)°	T = 100 K
V = 2256.35 (3) Å³	Prismatic needle, yellow
Z = 4	0.33 × 0.12 × 0.11 mm

Data collection top

Rigaku XtaLAB Synergy Dualflex HyPix diffractometer	4547 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube	R_int = 0.055
φ and ω scans	θ_max = 77.8°, θ_min = 3.8°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021)	h = −8→10
T_min = 0.411, T_max = 0.725	k = −24→24
30531 measured reflections	l = −18→18
4812 independent reflections

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0588P)² + 0.9267P] where P = (F_o² + 2F_c²)/3
4812 reflections	(Δ/σ)_max = 0.001
335 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.74119 (4)	0.62643 (2)	0.56167 (2)	0.01729 (11)
S2	0.51739 (4)	0.68042 (2)	0.70267 (2)	0.01806 (11)
O1	0.97431 (14)	0.86445 (5)	0.68665 (7)	0.0223 (2)
O2	0.59124 (13)	0.63170 (6)	0.50939 (7)	0.0225 (2)
O3	0.89353 (13)	0.65098 (5)	0.52573 (7)	0.0220 (2)
O4	1.14629 (16)	0.36623 (7)	0.68499 (9)	0.0341 (3)
O5	1.23988 (15)	0.46683 (7)	0.64260 (9)	0.0340 (3)
O6	0.43825 (13)	0.61417 (6)	0.70008 (8)	0.0241 (2)
O7	0.54611 (13)	0.71571 (6)	0.78814 (7)	0.0239 (2)
O8	0.32788 (17)	0.96375 (7)	0.51794 (10)	0.0377 (3)
O9	0.47463 (18)	0.94819 (6)	0.64251 (9)	0.0357 (3)
N1	0.71051 (15)	0.67238 (6)	0.65814 (8)	0.0179 (2)
N2	1.12743 (17)	0.42581 (7)	0.65689 (9)	0.0247 (3)
N3	0.38951 (18)	0.92648 (7)	0.57790 (10)	0.0278 (3)
C1	0.85072 (17)	0.68131 (7)	0.72031 (10)	0.0175 (3)
C2	0.94303 (17)	0.74318 (7)	0.71871 (10)	0.0186 (3)
C3	1.07789 (18)	0.74767 (8)	0.78022 (10)	0.0220 (3)
H3	1.1415	0.7892	0.7821	0.026*
C4	1.12052 (19)	0.69311 (9)	0.83828 (11)	0.0239 (3)
H4	1.2142	0.6972	0.8780	0.029*
C5	1.02746 (19)	0.63238 (8)	0.83891 (10)	0.0224 (3)
H5	1.0569	0.5949	0.8787	0.027*
C6	0.89046 (18)	0.62723 (7)	0.78039 (10)	0.0200 (3)
H6	0.8238	0.5866	0.7815	0.024*
C7	0.90565 (18)	0.80227 (8)	0.65835 (10)	0.0199 (3)
C8	0.82198 (19)	0.81274 (8)	0.57740 (11)	0.0224 (3)
H8	0.7638	0.7786	0.5424	0.027*
C9	0.8383 (2)	0.88476 (8)	0.55513 (11)	0.0242 (3)
H9	0.7929	0.9077	0.5025	0.029*
C10	0.9303 (2)	0.91413 (8)	0.62300 (11)	0.0238 (3)
C11	0.9849 (2)	0.98641 (8)	0.64350 (12)	0.0303 (4)
H11A	0.9245	1.0043	0.6966	0.045*
H11B	0.9628	1.0161	0.5897	0.045*
H11C	1.1034	0.9866	0.6577	0.045*
C12	0.77285 (17)	0.53925 (7)	0.59476 (10)	0.0183 (3)
C13	0.93448 (18)	0.51767 (8)	0.61163 (10)	0.0193 (3)
H13	1.0250	0.5487	0.6053	0.023*
C14	0.95731 (18)	0.44913 (8)	0.63798 (10)	0.0201 (3)
C15	0.8286 (2)	0.40242 (8)	0.64729 (10)	0.0227 (3)
H15	0.8491	0.3557	0.6658	0.027*
C16	0.66862 (19)	0.42513 (8)	0.62896 (10)	0.0228 (3)
H16	0.5788	0.3937	0.6342	0.027*
C17	0.63988 (18)	0.49387 (8)	0.60302 (10)	0.0203 (3)
H17	0.5306	0.5097	0.5911	0.024*
C18	0.41201 (17)	0.73702 (7)	0.62594 (10)	0.0190 (3)
C19	0.44463 (18)	0.80786 (8)	0.63208 (10)	0.0203 (3)
H19	0.5225	0.8258	0.6755	0.024*
C20	0.35845 (18)	0.85112 (8)	0.57207 (11)	0.0219 (3)
C21	0.24370 (19)	0.82640 (9)	0.50838 (11)	0.0248 (3)
H21	0.1887	0.8575	0.4672	0.030*
C22	0.21043 (19)	0.75567 (9)	0.50568 (11)	0.0254 (3)
H22	0.1298	0.7381	0.4635	0.030*
C23	0.29462 (18)	0.71020 (8)	0.56445 (11)	0.0221 (3)
H23	0.2724	0.6616	0.5627	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01830 (18)	0.01684 (18)	0.01676 (18)	0.00090 (11)	0.00114 (13)	−0.00100 (11)
S2	0.01788 (18)	0.01795 (18)	0.01841 (18)	0.00142 (12)	0.00264 (12)	0.00124 (12)
O1	0.0280 (5)	0.0168 (5)	0.0222 (5)	−0.0019 (4)	0.0030 (4)	0.0000 (4)
O2	0.0224 (5)	0.0235 (5)	0.0213 (5)	0.0036 (4)	−0.0038 (4)	−0.0022 (4)
O3	0.0243 (5)	0.0196 (5)	0.0222 (5)	−0.0006 (4)	0.0055 (4)	0.0000 (4)
O4	0.0361 (7)	0.0335 (6)	0.0329 (6)	0.0170 (5)	0.0079 (5)	0.0117 (5)
O5	0.0209 (6)	0.0362 (7)	0.0449 (7)	0.0040 (5)	0.0013 (5)	0.0015 (5)
O6	0.0231 (5)	0.0197 (5)	0.0296 (6)	−0.0012 (4)	0.0038 (4)	0.0043 (4)
O7	0.0242 (5)	0.0280 (6)	0.0195 (5)	0.0049 (4)	0.0022 (4)	−0.0011 (4)
O8	0.0431 (7)	0.0264 (6)	0.0436 (7)	0.0081 (5)	0.0027 (6)	0.0128 (5)
O9	0.0519 (8)	0.0216 (6)	0.0337 (7)	−0.0010 (5)	0.0018 (6)	−0.0020 (5)
N1	0.0170 (6)	0.0182 (6)	0.0184 (6)	0.0010 (4)	0.0010 (4)	−0.0020 (4)
N2	0.0251 (7)	0.0284 (7)	0.0207 (6)	0.0082 (5)	0.0039 (5)	−0.0002 (5)
N3	0.0324 (7)	0.0216 (7)	0.0297 (7)	0.0050 (5)	0.0085 (6)	0.0032 (5)
C1	0.0161 (6)	0.0195 (7)	0.0169 (6)	0.0005 (5)	0.0016 (5)	−0.0019 (5)
C2	0.0188 (6)	0.0190 (7)	0.0181 (6)	0.0002 (5)	0.0042 (5)	−0.0008 (5)
C3	0.0206 (7)	0.0234 (7)	0.0220 (7)	−0.0033 (6)	0.0016 (5)	−0.0023 (6)
C4	0.0205 (7)	0.0304 (8)	0.0207 (7)	−0.0003 (6)	−0.0009 (5)	−0.0005 (6)
C5	0.0243 (7)	0.0245 (7)	0.0184 (7)	0.0035 (6)	−0.0002 (6)	0.0022 (5)
C6	0.0217 (7)	0.0189 (7)	0.0194 (7)	−0.0006 (5)	0.0036 (5)	−0.0003 (5)
C7	0.0205 (7)	0.0172 (6)	0.0221 (7)	−0.0010 (5)	0.0049 (5)	−0.0022 (5)
C8	0.0243 (7)	0.0195 (7)	0.0235 (7)	−0.0012 (5)	0.0011 (6)	0.0016 (5)
C9	0.0265 (7)	0.0206 (7)	0.0257 (8)	0.0007 (6)	0.0033 (6)	0.0041 (6)
C10	0.0276 (7)	0.0185 (7)	0.0257 (7)	0.0014 (6)	0.0083 (6)	0.0022 (6)
C11	0.0398 (9)	0.0199 (7)	0.0315 (8)	−0.0020 (6)	0.0061 (7)	−0.0004 (6)
C12	0.0197 (7)	0.0173 (6)	0.0179 (6)	0.0013 (5)	0.0017 (5)	−0.0019 (5)
C13	0.0186 (7)	0.0210 (7)	0.0182 (6)	−0.0007 (5)	0.0023 (5)	−0.0019 (5)
C14	0.0209 (7)	0.0221 (7)	0.0172 (6)	0.0044 (5)	0.0014 (5)	−0.0021 (5)
C15	0.0312 (8)	0.0187 (7)	0.0181 (7)	0.0004 (6)	0.0009 (6)	−0.0011 (5)
C16	0.0266 (7)	0.0218 (7)	0.0199 (7)	−0.0060 (6)	0.0001 (6)	−0.0011 (5)
C17	0.0193 (7)	0.0225 (7)	0.0190 (7)	−0.0018 (5)	0.0001 (5)	−0.0020 (5)
C18	0.0167 (6)	0.0197 (7)	0.0207 (7)	0.0030 (5)	0.0040 (5)	0.0005 (5)
C19	0.0205 (7)	0.0202 (7)	0.0202 (7)	0.0021 (5)	0.0042 (5)	−0.0009 (5)
C20	0.0229 (7)	0.0187 (7)	0.0243 (7)	0.0039 (5)	0.0072 (6)	0.0019 (6)
C21	0.0217 (7)	0.0293 (8)	0.0235 (7)	0.0071 (6)	0.0040 (6)	0.0048 (6)
C22	0.0199 (7)	0.0312 (8)	0.0250 (7)	0.0024 (6)	−0.0006 (6)	−0.0011 (6)
C23	0.0182 (7)	0.0237 (7)	0.0245 (7)	0.0005 (5)	0.0021 (5)	−0.0014 (6)

Geometric parameters (Å, º) top

S1—O2	1.4269 (11)	C8—C9	1.427 (2)
S1—O3	1.4274 (11)	C8—H8	0.9500
S1—N1	1.6752 (12)	C9—C10	1.350 (2)
S1—C12	1.7591 (15)	C9—H9	0.9500
S2—O6	1.4249 (11)	C10—C11	1.485 (2)
S2—O7	1.4283 (11)	C11—H11A	0.9800
S2—N1	1.7089 (12)	C11—H11B	0.9800
S2—C18	1.7667 (15)	C11—H11C	0.9800
O1—C10	1.3709 (19)	C12—C17	1.393 (2)
O1—C7	1.3773 (18)	C12—C13	1.393 (2)
O4—N2	1.2231 (18)	C13—C14	1.382 (2)
O5—N2	1.2247 (19)	C13—H13	0.9500
O8—N3	1.227 (2)	C14—C15	1.384 (2)
O9—N3	1.228 (2)	C15—C16	1.390 (2)
N1—C1	1.4507 (18)	C15—H15	0.9500
N2—C14	1.4720 (19)	C16—C17	1.391 (2)
N3—C20	1.471 (2)	C16—H16	0.9500
C1—C6	1.390 (2)	C17—H17	0.9500
C1—C2	1.404 (2)	C18—C19	1.388 (2)
C2—C3	1.404 (2)	C18—C23	1.393 (2)
C2—C7	1.462 (2)	C19—C20	1.385 (2)
C3—C4	1.385 (2)	C19—H19	0.9500
C3—H3	0.9500	C20—C21	1.385 (2)
C4—C5	1.389 (2)	C21—C22	1.385 (2)
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.392 (2)	C22—C23	1.392 (2)
C5—H5	0.9500	C22—H22	0.9500
C6—H6	0.9500	C23—H23	0.9500
C7—C8	1.362 (2)

O2—S1—O3	121.18 (7)	C10—C9—H9	126.5
O2—S1—N1	105.71 (6)	C8—C9—H9	126.5
O3—S1—N1	105.68 (6)	C9—C10—O1	109.63 (13)
O2—S1—C12	109.40 (7)	C9—C10—C11	134.12 (15)
O3—S1—C12	106.87 (6)	O1—C10—C11	116.20 (14)
N1—S1—C12	107.24 (6)	C10—C11—H11A	109.5
O6—S2—O7	120.94 (7)	C10—C11—H11B	109.5
O6—S2—N1	108.91 (6)	H11A—C11—H11B	109.5
O7—S2—N1	103.39 (6)	C10—C11—H11C	109.5
O6—S2—C18	108.60 (7)	H11A—C11—H11C	109.5
O7—S2—C18	109.02 (7)	H11B—C11—H11C	109.5
N1—S2—C18	104.78 (6)	C17—C12—C13	121.75 (13)
C10—O1—C7	107.60 (12)	C17—C12—S1	120.58 (11)
C1—N1—S1	117.17 (9)	C13—C12—S1	117.67 (11)
C1—N1—S2	117.94 (9)	C14—C13—C12	116.99 (13)
S1—N1—S2	120.70 (7)	C14—C13—H13	121.5
O4—N2—O5	124.61 (14)	C12—C13—H13	121.5
O4—N2—C14	117.32 (13)	C13—C14—C15	123.07 (14)
O5—N2—C14	118.07 (13)	C13—C14—N2	117.55 (13)
O8—N3—O9	124.14 (15)	C15—C14—N2	119.37 (13)
O8—N3—C20	117.73 (15)	C14—C15—C16	118.73 (14)
O9—N3—C20	118.13 (13)	C14—C15—H15	120.6
C6—C1—C2	121.55 (13)	C16—C15—H15	120.6
C6—C1—N1	118.27 (12)	C15—C16—C17	120.10 (14)
C2—C1—N1	120.18 (12)	C15—C16—H16	119.9
C3—C2—C1	116.87 (13)	C17—C16—H16	119.9
C3—C2—C7	119.05 (13)	C16—C17—C12	119.34 (14)
C1—C2—C7	124.08 (13)	C16—C17—H17	120.3
C4—C3—C2	121.68 (14)	C12—C17—H17	120.3
C4—C3—H3	119.2	C19—C18—C23	122.06 (14)
C2—C3—H3	119.2	C19—C18—S2	118.18 (12)
C3—C4—C5	120.55 (14)	C23—C18—S2	119.69 (11)
C3—C4—H4	119.7	C20—C19—C18	116.97 (14)
C5—C4—H4	119.7	C20—C19—H19	121.5
C4—C5—C6	118.98 (14)	C18—C19—H19	121.5
C4—C5—H5	120.5	C19—C20—C21	122.77 (14)
C6—C5—H5	120.5	C19—C20—N3	118.00 (14)
C1—C6—C5	120.32 (13)	C21—C20—N3	119.22 (14)
C1—C6—H6	119.8	C20—C21—C22	118.91 (15)
C5—C6—H6	119.8	C20—C21—H21	120.5
C8—C7—O1	108.84 (13)	C22—C21—H21	120.5
C8—C7—C2	136.62 (14)	C21—C22—C23	120.27 (15)
O1—C7—C2	114.51 (13)	C21—C22—H22	119.9
C7—C8—C9	106.95 (14)	C23—C22—H22	119.9
C7—C8—H8	126.5	C22—C23—C18	118.97 (14)
C9—C8—H8	126.5	C22—C23—H23	120.5
C10—C9—C8	106.96 (14)	C18—C23—H23	120.5

O2—S1—N1—C1	−174.19 (10)	O2—S1—C12—C17	−25.39 (14)
O3—S1—N1—C1	−44.58 (11)	O3—S1—C12—C17	−158.26 (11)
C12—S1—N1—C1	69.16 (11)	N1—S1—C12—C17	88.80 (13)
O2—S1—N1—S2	29.26 (10)	O2—S1—C12—C13	154.26 (11)
O3—S1—N1—S2	158.87 (8)	O3—S1—C12—C13	21.39 (13)
C12—S1—N1—S2	−87.39 (9)	N1—S1—C12—C13	−91.55 (12)
O6—S2—N1—C1	−112.41 (11)	C17—C12—C13—C14	−0.6 (2)
O7—S2—N1—C1	17.40 (12)	S1—C12—C13—C14	179.70 (10)
C18—S2—N1—C1	131.55 (11)	C12—C13—C14—C15	0.4 (2)
O6—S2—N1—S1	43.96 (10)	C12—C13—C14—N2	−179.44 (12)
O7—S2—N1—S1	173.77 (8)	O4—N2—C14—C13	176.14 (13)
C18—S2—N1—S1	−72.08 (9)	O5—N2—C14—C13	−4.6 (2)
S1—N1—C1—C6	−81.02 (15)	O4—N2—C14—C15	−3.7 (2)
S2—N1—C1—C6	76.19 (15)	O5—N2—C14—C15	175.51 (14)
S1—N1—C1—C2	98.73 (14)	C13—C14—C15—C16	0.3 (2)
S2—N1—C1—C2	−104.06 (13)	N2—C14—C15—C16	−179.83 (13)
C6—C1—C2—C3	0.4 (2)	C14—C15—C16—C17	−0.9 (2)
N1—C1—C2—C3	−179.36 (12)	C15—C16—C17—C12	0.7 (2)
C6—C1—C2—C7	−178.88 (13)	C13—C12—C17—C16	0.1 (2)
N1—C1—C2—C7	1.4 (2)	S1—C12—C17—C16	179.75 (11)
C1—C2—C3—C4	1.5 (2)	O6—S2—C18—C19	166.10 (11)
C7—C2—C3—C4	−179.21 (14)	O7—S2—C18—C19	32.49 (13)
C2—C3—C4—C5	−1.6 (2)	N1—S2—C18—C19	−77.64 (12)
C3—C4—C5—C6	−0.1 (2)	O6—S2—C18—C23	−11.09 (14)
C2—C1—C6—C5	−2.1 (2)	O7—S2—C18—C23	−144.70 (12)
N1—C1—C6—C5	177.64 (13)	N1—S2—C18—C23	105.16 (12)
C4—C5—C6—C1	1.9 (2)	C23—C18—C19—C20	−1.9 (2)
C10—O1—C7—C8	0.89 (16)	S2—C18—C19—C20	−179.03 (10)
C10—O1—C7—C2	179.24 (12)	C18—C19—C20—C21	0.3 (2)
C3—C2—C7—C8	158.66 (17)	C18—C19—C20—N3	179.36 (12)
C1—C2—C7—C8	−22.1 (3)	O8—N3—C20—C19	171.70 (14)
C3—C2—C7—O1	−19.06 (19)	O9—N3—C20—C19	−8.6 (2)
C1—C2—C7—O1	160.19 (13)	O8—N3—C20—C21	−9.2 (2)
O1—C7—C8—C9	−0.59 (17)	O9—N3—C20—C21	170.48 (14)
C2—C7—C8—C9	−178.40 (16)	C19—C20—C21—C22	1.5 (2)
C7—C8—C9—C10	0.06 (18)	N3—C20—C21—C22	−177.54 (13)
C8—C9—C10—O1	0.49 (17)	C20—C21—C22—C23	−1.8 (2)
C8—C9—C10—C11	−176.60 (17)	C21—C22—C23—C18	0.2 (2)
C7—O1—C10—C9	−0.86 (16)	C19—C18—C23—C22	1.7 (2)
C7—O1—C10—C11	176.82 (13)	S2—C18—C23—C22	178.77 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.95	2.41	2.7460 (18)	101
C3—H3···O4ⁱ	0.95	2.31	3.226 (2)	161
C13—H13···O3	0.95	2.51	2.8637 (18)	102
C16—H16···O2ⁱⁱ	0.95	2.53	3.0874 (18)	118
C19—H19···O4ⁱⁱⁱ	0.95	2.58	2.981 (2)	106
C23—H23···O6	0.95	2.56	2.9252 (19)	103

Symmetry codes: (i) −x+5/2, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, y+1/2, −z+3/2.

Summary of short interatomic contacts (Å). top

Contact	Distance	Symmetry operation
N2···O3	3.03	-x+2, -y+1, -z+1
H19···H15	2.58	-x+3/2, y+1/2, -z+3/2
H16···O2	2.53	-x+1, -y+1, -z+1
O5···H17	2.62	x+1, y, z
O4···H3	2.31	-x+5/2, y-1/2, -z+3/2
H4···H8	2.46	x+1/2, -y+3/2, z+1/2
H9···O8	2.67	-x+1, -y+2, -z+1

Acknowledgements

GMZ thanks to Baku State University for financial support. The contributions of the authors are as follows: conceptualization, MA and AB; synthesis, SA and GMB; X-ray analysis, GZM, VNK, MA and SÖY; writing (review and editing of the manuscript), MA and AB; funding acquisition, GZM; supervision, MA and AB.

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