Synthesis and crystal structure of catena-poly[[[aqua­{2-[(E)-(1-cyano-2-imino-2-meth­oxy­ethyl­idene)hydrazin­yl]benzene­sulfonato}­sodium]-di-μ-aqua] dihydrate]

Aliyeva, V.A.; Aliyeva, F.S.; Akkurt, M.; Yıldırım, S. Ö.; Bhattarai, A.

doi:10.1107/S2056989023003602

research communications

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ISSN: 2056-9890

Volume 79| Part 5| May 2023| Pages 508-511

https://doi.org/10.1107/S2056989023003602

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Synthesis and crystal structure of catena-poly[[[aqua{2-[(E)-(1-cyano-2-imino-2-methoxyethylidene)hydrazinyl]benzenesulfonato}sodium]-di-μ-aqua] dihydrate]

Vusala A. Aliyeva,^a Fargana S. Aliyeva,^b Mehmet Akkurt,^c Sema Öztürk Yıldırım ^d,^c and Ajaya Bhattarai ^e ^*

^aCentro de Química Estrutural, Institute of Molecular Sciences, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal, ^bExcellence Center, Baku State University, Z. Xalilov Str. 23, Az 1148 Baku, Azerbaijan, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, ^dDepartment of Physics, Faculty of Science, Eskisehir Technical University, Yunus Emre Campus, 26470 Eskisehir, Türkiye, and ^eDepartment of Chemistry, M.M.A.M.C. (Tribhuvan University), Biratnagar, Nepal
^*Correspondence e-mail: bkajaya@yahoo.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 3 April 2023; accepted 20 April 2023; online 28 April 2023)

In the polymeric title compound, {[Na(C₁₀H₉N₄O₄S)(H₂O)₃]·2H₂O}_n, sixfold coordinated Na⁺ cations are linked into a chain parallel to [010] by sharing common water molecules. Next to the four bridging water molecules, each Na⁺ cation of the chain is bonded to the O atom of a terminal water molecule and an O atom of the SO₃⁻ group of the sulfonate anion. Classical O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds and additional π–π interactions connect these chains into a three-dimensional network.

Keywords: crystal structure; hydrogen bonds; π–π stacking interaction; chain structure; hydrazone.

CCDC reference: 2257827

1. Chemical context

Hydrazones are interesting compounds in the fields of coordination chemistry, crystal engineering, catalysis, molecular recoginition and synthetic organic chemistry (Ma et al., 2021 ; Mahmoudi et al., 2017a ,b , 2019 ). Depending on the attached functional groups of the hydrazone ligands, the solubility and catalytic activities of their corresponding metal complexes can be improved (Gurbanov et al., 2022 ). Hydrazones have been applied as analytical reagents (Mahmudov et al., 2010 ), as well as building blocks in the construction of supramolecular networks, owing to their capabilities as donor and acceptor groups in hydrogen bonding (Maharramov et al., 2010 ; Mahmudov et al., 2011 , 2012 , 2013 ). Both resonance-assisted hydrogen or chalcogen bonds also play a crucial role in the synthesis and structural chemistry of hydrazone ligands (Gurbanov et al., 2020a ,b ; Mahmudov et al., 2022 ). Similar to other classes of N-containing ligands, hydrazones also participate in various types of intermolecular interactions (Polyanskii et al., 2019 ; Zubkov et al., 2018 ).

Herein, we report the structural features of the hydrazone derivative poly[[di-μ-aqua-{2-[(E)-(1-cyano-2-imino-2-methoxyethylidene)hydrazinyl]benzenesulfonato}sodium] dihydrate].

2. Structural commentary

The Na⁺ cation exhibits a six-coordination by O atoms in the form of a distorted octahedron. Four water molecules (O7, O9 and their symmetry-related counterparts) bridge adjacent cations into a chain extending parallel to [010] (Fig. 1). The coordination sphere is completed by the O atoms of another water molecule (O8), now bonded terminally, and an O atom from the SO₃⁻ group (O2). The sulfonate anion shows no atypical features.

Figure 1
The coordination environment of the Na⁺ cations in the title compound, leading to the formation of a chain extending parallel to [010]. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (a) −x, −y, −z + 1; (b) −x, −y + 1, −z + 1.]

3. Supramolecular features

Classical O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds of medium strength (Table 1) form a three-dimensional network (Figs. 2 and 3). Furthermore, the molecules are linked by π–π stacking interactions between the benzene rings [Cg1⋯Cg1(−x + 1, −y + 1, −z + 1) = 3.7588 (8) Å and slippage = 1.684 Å, where Cg1 is the centroid of the C1–C6 ring] parallel to [010] (Fig. 4).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O4ⁱ	0.85	1.98	2.8243 (13)	173
O5—H5B⋯O6ⁱⁱ	0.85	1.92	2.7660 (13)	176
O6—H6A⋯O5	0.85	1.88	2.7295 (15)	174
O6—H6B⋯O3	0.85	1.98	2.8169 (13)	168
O7—H7A⋯O5ⁱⁱⁱ	0.85	2.06	2.8978 (13)	171
O7—H7B⋯N4^iv	0.85	1.98	2.8141 (14)	167
O8—H8A⋯O3^v	0.85	2.05	2.8874 (14)	168
O8—H8B⋯O2^vi	0.85	2.18	2.9689 (15)	153
O9—H9A⋯O6	0.85	1.97	2.8241 (14)	178
N4—H4N⋯O8^vii	0.93	2.38	3.0905 (16)	133
Symmetry codes: (i) x, y+1, z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) ; (iv) ; (v) ; (vi) ; (vii) x+1, y, z.

Figure 2
View of the crystal structure along [010], with O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds shown as dashed lines.

Figure 3
View of the crystal structure along [001]; the hydrogen bonds are as in Fig. 2

Figure 4
The π–π stacking interactions in the title compound shown with dashed lines.

4. Database survey

A search in the Cambridge Structural Database (CSD, Version 5.42, September 2021 update; Groom et al., 2016 ) for related benzenesulfonates with a monovalent cation gave two matches. In catena-[bis(μ₄-3-carboxy-4-hydroxybenzenesulfonato)triaquadisilver(I) monohydrate] (CSD refcode FETHES; Gao et al., 2005 ), both substituted benzenesulfonate anions use two of their sulfonyl O atoms to link to three Ag⁺ cations and their carbonyl O atom to another Ag⁺ cation in a μ₄-binding mode. The two symmetry-independent Ag⁺ cations are additionally coordinated by water molecules, one by one water molecule and the other by two water molecules, so that one Ag⁺ cation is five- and the other six-coordinate. In catena-[μ₅-(3-carboxy-4-hydroxybenzenesulfonate)(μ₂-aqua)rubidium] (FAXGAN; Hu et al., 2005 ), the 3-carboxy-4-hydroxybenzenesulfonate anion retains the usual intermolecular hydrogen bond between the phenol and carboxyl O atoms. The Rb⁺ cation is surrounded by eight O atoms, and the crystal packing is stabilized by intermolecular O—H⋯O hydrogen bonds.

5. Synthesis and crystallization

344 mg (1 mmol) of sodium 2-[2-(dicyanomethylene)hydrazinyl]benzenesulfonate tetrahydrate (Kopylovich et al., 2013 ) were dissolved in 60 ml of methanol and refluxed for 6 h. The reaction mixture was kept in air at room temperature for slow evaporation. After ca 2–3 d, yellow crystals of the title compound, suitable for X-ray analysis, had formed (yield 84%). The crystals were soluble in DMSO, ethanol and dimethylformamide and insoluble in nonpolar solvents. Elemental analysis (%) for C₁₀H₁₉N₄NaO₉S: C 30.41 (calc. 30.46), H 4.83 (4.86), N 14.16 (14.21); IR (KBr): 3390 ν(OH), 2995 and 2867 ν(NH), 1653 ν(C=N) cm⁻¹. ¹H NMR in DMSO, internal TMS: δ (ppm) 3.44 (3H, OCH₃), 7.16–8.11 (4H, Ar—H), 10.19 (1H, NH), 14.11 (s, 1H, N—H). ¹³C NMR in DMSO, internal TMS: δ (ppm) 58.2 (OCH₃), 111.5 (C=N), 112.3 (C≡N), 123.6 (ArC—H), 121.7 (ArC—SO₃Na), 122.2 (ArC—H), 126.8 (ArC—H), 129.1 (ArC—H), 142.5 (ArC—NH) and 160.0 (C=NH).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. C-bound H atoms were positioned geometrically (C—H = 0.95 and 0.98 Å) and refined using a riding model, with U_iso(H) = 1.2 or 1.5U_eq(C). O- and N-bound H atoms were located from difference Fourier maps and refined with U_iso(H) = 1.2U_eq(N) and 1.5U_eq(O), with their positions fixed at distances of N—H = 0.93 Å and O—H = 0.85 Å.

Table 2
Experimental details

Crystal data
Chemical formula	[Na(C₁₀H₉N₄O₄S)(H₂O)₃]·2H₂O
M_r	394.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	13.3305 (5), 6.8212 (3), 20.9547 (8)
β (°)	106.681 (1)
V (Å³)	1825.23 (13)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.25
Crystal size (mm)	0.27 × 0.21 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.926, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	27710, 3748, 3389
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.081, 1.07
No. of reflections	3748
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.36
Computer programs: APEX2 and SAINT (Bruker, 2007 ), SHELXS (Sheldrick, 2008 ), SHELXL2019 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2257827

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989023003602/wm5680sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023003602/wm5680Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2019 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

catena-Poly[[[aqua{2-[(E)-(1-cyano-2-imino-2-methoxyethylidene)hydrazinyl]benzenesulfonato}sodium]-di-µ-aqua] dihydrate] top

Crystal data top

[Na(C₁₀H₉N₄O₄S)(H₂O)₃]·2H₂O	F(000) = 824
M_r = 394.34	D_x = 1.435 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.3305 (5) Å	Cell parameters from 9914 reflections
b = 6.8212 (3) Å	θ = 3.2–26.5°
c = 20.9547 (8) Å	µ = 0.25 mm⁻¹
β = 106.681 (1)°	T = 150 K
V = 1825.23 (13) Å³	Needle, yellow
Z = 4	0.27 × 0.21 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	3389 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.021
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 26.5°, θ_min = 2.2°
T_min = 0.926, T_max = 0.967	h = −16→16
27710 measured reflections	k = −8→7
3748 independent reflections	l = −26→26

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.028	Hydrogen site location: mixed
wR(F²) = 0.081	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0397P)² + 0.8377P] where P = (F_o² + 2F_c²)/3
3748 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.36 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
Na1	0.01633 (4)	0.24885 (7)	0.50226 (3)	0.02094 (13)
S1	0.24044 (2)	0.24765 (4)	0.43523 (2)	0.01763 (9)
O1	0.64543 (8)	0.03548 (17)	0.26660 (5)	0.0316 (2)
O2	0.16843 (7)	0.18478 (17)	0.47128 (5)	0.0312 (2)
O3	0.21772 (7)	0.44290 (14)	0.40648 (5)	0.0250 (2)
O4	0.24943 (7)	0.10353 (15)	0.38547 (5)	0.0292 (2)
O5	0.05048 (7)	0.95638 (15)	0.31489 (4)	0.0259 (2)
H5A	0.111073	1.003570	0.332701	0.039*
H5B	0.026423	0.994300	0.274741	0.039*
O6	0.02512 (8)	0.55977 (15)	0.31795 (5)	0.0278 (2)
H6A	0.036537	0.682516	0.319429	0.042*
H6B	0.083707	0.512606	0.340269	0.042*
O7	−0.05415 (7)	0.00275 (14)	0.41756 (4)	0.0214 (2)
H7A	−0.029422	−0.003553	0.384492	0.032*
H7B	−0.116822	0.035287	0.397482	0.032*
O8	−0.15677 (8)	0.24814 (14)	0.51810 (5)	0.0267 (2)
H8A	−0.183026	0.329914	0.539397	0.040*
H8B	−0.170926	0.135404	0.530527	0.040*
O9	−0.07335 (8)	0.48983 (15)	0.41848 (5)	0.0292 (2)
H9A	−0.044937	0.508569	0.387489	0.044*
H9B	−0.120247	0.402548	0.405278	0.044*
N1	0.45695 (8)	0.19223 (16)	0.41179 (5)	0.0173 (2)
H1N	0.394133	0.153936	0.384683	0.021*
N2	0.54648 (8)	0.17969 (16)	0.39713 (5)	0.0184 (2)
N3	0.37653 (11)	0.0270 (2)	0.24994 (7)	0.0407 (3)
N4	0.73936 (9)	0.1439 (2)	0.37031 (6)	0.0331 (3)
H4N	0.728594	0.183478	0.410070	0.040*
C1	0.45890 (9)	0.23787 (17)	0.47751 (6)	0.0160 (2)
C2	0.55436 (10)	0.25797 (18)	0.52682 (7)	0.0203 (3)
H2	0.618229	0.240330	0.515954	0.024*
C3	0.55603 (11)	0.3035 (2)	0.59141 (6)	0.0243 (3)
H3	0.621321	0.316534	0.624649	0.029*
C4	0.46382 (11)	0.3304 (2)	0.60838 (6)	0.0254 (3)
H4	0.465840	0.363154	0.652795	0.030*
C5	0.36862 (10)	0.30915 (19)	0.55994 (6)	0.0220 (3)
H5	0.305188	0.326402	0.571371	0.026*
C6	0.36531 (9)	0.26271 (17)	0.49470 (6)	0.0167 (2)
C7	0.54846 (10)	0.12221 (19)	0.33855 (6)	0.0206 (3)
C8	0.65335 (10)	0.1044 (2)	0.32786 (6)	0.0254 (3)
C9	0.45515 (11)	0.0676 (2)	0.28728 (6)	0.0253 (3)
C10	0.74403 (13)	0.0023 (3)	0.25222 (8)	0.0457 (5)
H10C	0.730573	−0.048535	0.206797	0.069*
H10D	0.785594	−0.093168	0.283906	0.069*
H10E	0.782662	0.126071	0.256239	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0226 (3)	0.0185 (3)	0.0246 (3)	0.00087 (19)	0.0112 (2)	0.00084 (19)
S1	0.01257 (15)	0.01943 (17)	0.02187 (16)	−0.00042 (10)	0.00653 (12)	0.00011 (11)
O1	0.0268 (5)	0.0499 (7)	0.0209 (5)	0.0097 (5)	0.0111 (4)	−0.0017 (4)
O2	0.0193 (5)	0.0428 (6)	0.0354 (5)	−0.0046 (4)	0.0140 (4)	0.0061 (5)
O3	0.0219 (4)	0.0237 (5)	0.0267 (5)	0.0024 (4)	0.0027 (4)	0.0043 (4)
O4	0.0163 (4)	0.0326 (5)	0.0361 (5)	−0.0006 (4)	0.0034 (4)	−0.0151 (4)
O5	0.0229 (4)	0.0335 (5)	0.0192 (4)	−0.0052 (4)	0.0025 (4)	0.0012 (4)
O6	0.0286 (5)	0.0276 (5)	0.0229 (5)	0.0014 (4)	0.0007 (4)	0.0009 (4)
O7	0.0172 (4)	0.0256 (5)	0.0218 (4)	0.0030 (3)	0.0063 (3)	0.0015 (4)
O8	0.0287 (5)	0.0237 (5)	0.0316 (5)	0.0012 (4)	0.0147 (4)	−0.0001 (4)
O9	0.0352 (5)	0.0240 (5)	0.0305 (5)	−0.0043 (4)	0.0126 (4)	0.0006 (4)
N1	0.0139 (5)	0.0202 (5)	0.0183 (5)	−0.0010 (4)	0.0052 (4)	−0.0009 (4)
N2	0.0170 (5)	0.0173 (5)	0.0226 (5)	0.0020 (4)	0.0085 (4)	0.0034 (4)
N3	0.0338 (7)	0.0553 (9)	0.0308 (7)	−0.0053 (6)	0.0059 (6)	−0.0077 (6)
N4	0.0215 (6)	0.0581 (9)	0.0214 (5)	0.0079 (6)	0.0088 (5)	0.0006 (6)
C1	0.0175 (6)	0.0125 (5)	0.0180 (6)	−0.0012 (4)	0.0053 (5)	0.0013 (4)
C2	0.0172 (6)	0.0191 (6)	0.0233 (6)	−0.0015 (4)	0.0038 (5)	0.0011 (5)
C3	0.0259 (6)	0.0215 (6)	0.0211 (6)	−0.0039 (5)	−0.0005 (5)	0.0009 (5)
C4	0.0372 (7)	0.0224 (7)	0.0165 (6)	−0.0018 (6)	0.0076 (5)	−0.0009 (5)
C5	0.0270 (6)	0.0195 (6)	0.0230 (6)	0.0003 (5)	0.0125 (5)	0.0008 (5)
C6	0.0169 (6)	0.0141 (6)	0.0194 (6)	−0.0003 (4)	0.0059 (5)	0.0014 (4)
C7	0.0208 (6)	0.0220 (6)	0.0202 (6)	0.0030 (5)	0.0079 (5)	0.0028 (5)
C8	0.0237 (6)	0.0334 (7)	0.0220 (6)	0.0083 (5)	0.0111 (5)	0.0053 (5)
C9	0.0275 (7)	0.0299 (7)	0.0214 (6)	0.0019 (6)	0.0118 (5)	−0.0008 (5)
C10	0.0317 (8)	0.0826 (14)	0.0273 (7)	0.0189 (8)	0.0155 (6)	−0.0014 (8)

Geometric parameters (Å, º) top

Na1—O2	2.3407 (11)	O9—H9B	0.8500
Na1—O7ⁱ	2.3530 (10)	N1—N2	1.3178 (14)
Na1—O9ⁱⁱ	2.4061 (11)	N1—C1	1.4049 (15)
Na1—O8	2.4237 (11)	N1—H1N	0.9050
Na1—O7	2.4276 (10)	N2—C7	1.2961 (16)
Na1—O9	2.4511 (11)	N3—C9	1.1474 (19)
Na1—Na1ⁱ	3.4206 (10)	N4—C8	1.2621 (18)
Na1—Na1ⁱⁱ	3.4517 (10)	N4—H4N	0.9254
Na1—H9B	2.5336	C1—C2	1.3967 (17)
S1—O2	1.4466 (9)	C1—C6	1.4045 (17)
S1—O3	1.4572 (10)	C2—C3	1.3826 (19)
S1—O4	1.4627 (10)	C2—H2	0.9500
S1—C6	1.7730 (13)	C3—C4	1.386 (2)
O1—C8	1.3424 (16)	C3—H3	0.9500
O1—C10	1.4482 (17)	C4—C5	1.3864 (19)
O5—H5A	0.8498	C4—H4	0.9500
O5—H5B	0.8501	C5—C6	1.3916 (18)
O6—H6A	0.8500	C5—H5	0.9500
O6—H6B	0.8500	C7—C9	1.4398 (18)
O7—H7A	0.8496	C7—C8	1.4832 (17)
O7—H7B	0.8500	C10—H10C	0.9800
O8—H8A	0.8500	C10—H10D	0.9800
O8—H8B	0.8503	C10—H10E	0.9800
O9—H9A	0.8501

O2—Na1—O7ⁱ	92.10 (4)	Na1ⁱ—O7—H7B	121.5
O2—Na1—O9ⁱⁱ	101.69 (4)	Na1—O7—H7B	107.5
O7ⁱ—Na1—O9ⁱⁱ	94.98 (4)	H7A—O7—H7B	99.5
O2—Na1—O8	166.44 (4)	Na1—O8—H8A	128.5
O7ⁱ—Na1—O8	85.30 (3)	Na1—O8—H8B	110.3
O9ⁱⁱ—Na1—O8	91.80 (4)	H8A—O8—H8B	105.8
O2—Na1—O7	81.51 (4)	Na1ⁱⁱ—O9—Na1	90.57 (4)
O7ⁱ—Na1—O7	88.64 (3)	Na1ⁱⁱ—O9—H9A	107.1
O9ⁱⁱ—Na1—O7	175.04 (4)	Na1—O9—H9A	114.5
O8—Na1—O7	85.12 (3)	Na1ⁱⁱ—O9—H9B	143.2
O2—Na1—O9	102.11 (4)	Na1—O9—H9B	85.7
O7ⁱ—Na1—O9	163.96 (4)	H9A—O9—H9B	107.7
O9ⁱⁱ—Na1—O9	89.43 (4)	N2—N1—C1	118.67 (10)
O8—Na1—O9	79.14 (4)	N2—N1—H1N	124.9
O7—Na1—O9	86.18 (4)	C1—N1—H1N	115.6
O2—Na1—Na1ⁱ	85.44 (3)	C7—N2—N1	120.42 (11)
O7ⁱ—Na1—Na1ⁱ	45.20 (3)	C8—N4—H4N	110.6
O9ⁱⁱ—Na1—Na1ⁱ	140.07 (4)	C2—C1—C6	119.09 (11)
O8—Na1—Na1ⁱ	83.29 (3)	C2—C1—N1	120.22 (11)
O7—Na1—Na1ⁱ	43.45 (2)	C6—C1—N1	120.68 (11)
O9—Na1—Na1ⁱ	127.86 (4)	C3—C2—C1	120.10 (12)
O2—Na1—Na1ⁱⁱ	106.87 (4)	C3—C2—H2	120.0
O7ⁱ—Na1—Na1ⁱⁱ	137.99 (4)	C1—C2—H2	120.0
O9ⁱⁱ—Na1—Na1ⁱⁱ	45.24 (3)	C2—C3—C4	120.96 (12)
O8—Na1—Na1ⁱⁱ	83.58 (3)	C2—C3—H3	119.5
O7—Na1—Na1ⁱⁱ	130.32 (3)	C4—C3—H3	119.5
O9—Na1—Na1ⁱⁱ	44.19 (3)	C3—C4—C5	119.41 (12)
Na1ⁱ—Na1—Na1ⁱⁱ	166.02 (3)	C3—C4—H4	120.3
O2—Na1—H9B	109.6	C5—C4—H4	120.3
O7ⁱ—Na1—H9B	146.3	C4—C5—C6	120.48 (12)
O9ⁱⁱ—Na1—H9B	105.0	C4—C5—H5	119.8
O8—Na1—H9B	67.5	C6—C5—H5	119.8
O7—Na1—H9B	70.2	C5—C6—C1	119.95 (11)
O9—Na1—H9B	19.5	C5—C6—S1	117.54 (10)
Na1ⁱ—Na1—H9B	109.4	C1—C6—S1	122.45 (9)
Na1ⁱⁱ—Na1—H9B	60.7	N2—C7—C9	122.47 (11)
O2—S1—O3	113.36 (6)	N2—C7—C8	116.37 (11)
O2—S1—O4	112.05 (6)	C9—C7—C8	121.07 (11)
O3—S1—O4	111.68 (6)	N4—C8—O1	123.70 (12)
O2—S1—C6	106.26 (6)	N4—C8—C7	125.53 (12)
O3—S1—C6	106.22 (5)	O1—C8—C7	110.75 (11)
O4—S1—C6	106.71 (5)	N3—C9—C7	174.65 (14)
C8—O1—C10	115.26 (11)	O1—C10—H10C	109.5
S1—O2—Na1	147.89 (7)	O1—C10—H10D	109.5
H5A—O5—H5B	111.1	H10C—C10—H10D	109.5
H6A—O6—H6B	103.1	O1—C10—H10E	109.5
Na1ⁱ—O7—Na1	91.36 (3)	H10C—C10—H10E	109.5
Na1ⁱ—O7—H7A	119.5	H10D—C10—H10E	109.5
Na1—O7—H7A	118.2

O3—S1—O2—Na1	5.69 (15)	N1—C1—C6—S1	−2.39 (16)
O4—S1—O2—Na1	−121.84 (12)	O2—S1—C6—C5	−30.12 (12)
C6—S1—O2—Na1	121.98 (12)	O3—S1—C6—C5	90.88 (10)
C1—N1—N2—C7	174.30 (11)	O4—S1—C6—C5	−149.84 (10)
N2—N1—C1—C2	−3.68 (17)	O2—S1—C6—C1	152.62 (10)
N2—N1—C1—C6	176.71 (11)	O3—S1—C6—C1	−86.38 (11)
C6—C1—C2—C3	−0.59 (18)	O4—S1—C6—C1	32.90 (12)
N1—C1—C2—C3	179.80 (11)	N1—N2—C7—C9	−0.71 (19)
C1—C2—C3—C4	−0.2 (2)	N1—N2—C7—C8	−177.34 (11)
C2—C3—C4—C5	0.7 (2)	C10—O1—C8—N4	1.9 (2)
C3—C4—C5—C6	−0.5 (2)	C10—O1—C8—C7	−176.78 (13)
C4—C5—C6—C1	−0.26 (19)	N2—C7—C8—N4	−1.5 (2)
C4—C5—C6—S1	−177.60 (10)	C9—C7—C8—N4	−178.15 (15)
C2—C1—C6—C5	0.81 (17)	N2—C7—C8—O1	177.19 (12)
N1—C1—C6—C5	−179.58 (11)	C9—C7—C8—O1	0.51 (18)
C2—C1—C6—S1	178.00 (9)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4ⁱⁱⁱ	0.85	1.98	2.8243 (13)	173
O5—H5B···O6^iv	0.85	1.92	2.7660 (13)	176
O6—H6A···O5	0.85	1.88	2.7295 (15)	174
O6—H6B···O3	0.85	1.98	2.8169 (13)	168
O7—H7A···O5^v	0.85	2.06	2.8978 (13)	171
O7—H7B···N4^vi	0.85	1.98	2.8141 (14)	167
O8—H8A···O3ⁱⁱ	0.85	2.05	2.8874 (14)	168
O8—H8B···O2ⁱ	0.85	2.18	2.9689 (15)	153
O9—H9A···O6	0.85	1.97	2.8241 (14)	178
N4—H4N···O8^vii	0.93	2.38	3.0905 (16)	133

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

Acknowledgements

VA thanks the Fundação para a Ciência e a Tecnologia (FCT) (Portugal), Associação do Instituto Superior Técnico para Investigação e Desenvolvimento for her research fellowship through grant No. BL110/2022-IST-ID and Baku State University. The contributions of the authors are as follows. Conceptualization, MA and AB; synthesis, VAA and FSA; X-ray analysis, VAA, SÖY and MA; writing (review and editing of the manuscript), MA and AB; funding acquisition, VAA and FSA; supervision, MA and AB.

Funding information

Funding for this research was provided by: Fundação para a Ciência e a Tecnologia (grant No. BL110/2022-IST-ID).

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