Tetra­aqua­(ethane-1,2-di­amine-κ2N,N′)nickel(II) naphthalene-1,5-di­sulfonate dihydrate

Suyunov, J.R.; Turaev, K.K.; Alimnazarov, B.K.; Ibragimov, A.B.; Mengnorov, I.J.; Rasulov, A.A.; Ashurov, J.M.

doi:10.1107/S2414314623010325

metal-organic compounds

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ISSN: 2414-3146

Volume 8| Part 12| December 2023| x231032

https://doi.org/10.1107/S2414314623010325

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Tetraaqua(ethane-1,2-diamine-κ²N,N′)nickel(II) naphthalene-1,5-disulfonate dihydrate

Jabbor R. Suyunov,^a Khayit Kh. Turaev,^a Bekmurod Kh. Alimnazarov,^a Aziz B. Ibragimov,^b Islombek J. Mengnorov,^b Abdusamat A. Rasulov ^c and Jamshid M. Ashurov ^c ^*

^aTermez State University, Barkamol Avlod Street 43, Termez City, Uzbekistan, ^bInstitute of General and Inorganic Chemistry of Uzbekistan Academy of Sciences, 100170, Mirzo Ulug'bek Str. 77a, Tashkent, Uzbekistan, and ^cInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, 100125, M. Ulugbek Str. 83, Tashkent, Uzbekistan
^*Correspondence e-mail: ashurovjamshid1@gmail.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 7 November 2023; accepted 30 November 2023; online 14 December 2023)

The reaction of ethane-1,2-diamine (en, C₂H₈N₂), the sodium salt of naphthalene-1,5-disulfonic acid (H₂NDS, C₁₀H₈O₆S₂), and nickel sulfate in an aqueous solution resulted in the formation of the title salt, [Ni(C₂H₈N₂)(H₂O)₄](C₁₀H₆O₆S₂)·2H₂O or [Ni(en)(H₂O)₄](NDS)·2H₂O. In the asymmetric unit, one half of an [Ni(en)(H₂O)₄]²⁺ cation and one half of an NDS²⁻ anion, and one water molecule of crystallization are present. The Ni²⁺ cation in the complex is positioned on a twofold rotation axis and exhibits a slight tetragonal distortion of the cis-NiO₄N₂ octahedron, with an Ni—N bond length of 2.0782 (16) Å, and Ni—O bond lengths of 2.1170 (13) Å and 2.0648 (14) Å. The anion is completed by inversion symmetry. In the extended structure, the cations, anions, and non-coordinating water molecules are connected by intermolecular N—H⋯O and O—H⋯O hydrogen bonding, as well as C—H⋯π interactions, forming a three-dimensional network.

Keywords: ethane-1,2-diamine; naphthalene-1,5-disulfonate; crystal structure; hydrogen bonding; C—H⋯π interaction.

CCDC reference: 2311309

Structure description

As known for decades, ethane-1,2-diamine (en) exhibits excellent coordination and chelating abilities, forming five-membered rings with the central metals. Generally, these metallacycles adopt a twist conformation. En ligands can coordinate with metal ions in a monodentate fashion (Xue et al., 2016 ; Mitzinger et al., 2016 ) and in some complexes, they can act as bridging ligands (Binnemans et al., 2013 ; Bratsos et al., 2011 ; Doring & Jones, 2013 ). In most cases, en demonstrates chelating properties (Ashurov et al., 2018 ; Qadir et al., 2020 ). There are also metal complexes where non-coordinating en molecules are present (Sun et al., 2017 ; Tian et al., 2017 ; Mirzaei et al., 2014 ).

Complexes derived from naphthalene-1,5-disulfonic acid (H₂NDS) are of great interest in supramolecular chemistry due to their ability to form hydrogen bonds (Shi et al., 2014 ; Xu et al., 2019 ; Chen et al., 2020 ; Suyunov et al., 2023 ), because the sulfonate group can accept up to six hydrogen bonds with its lone pairs (Oh et al., 2020 ; Chen et al., 2022 ). As a ligand, NDS²⁻ sometimes binds in a bridging mode (Lian & Qu, 2013 ; Das et al., 2015 ; Tai et al., 2015 ). As part of our work in this area, we now describe the synthesis and structure of the hydrated title salt [Ni(en)(H₂O)₄]⁺·NDS²⁻·2H₂O.

The asymmetric unit consists of one-half of the [Ni(en)(H₂O)₄]²⁺ complex cation, one half of the NDS²⁻ organic dianion, and a water molecule of crystallization. The Ni²⁺ cation in the complex is positioned on a twofold rotation axis and exhibits a slightly tetragonal distortion of the cis-NiO₄N₂ octahedron. The Ni—N bond length is 2.0782 (16) Å, and the Ni—O bond lengths are 2.1170 (13) Å and 2.0648 (14) Å, similar to those reported for other [Ni(en)(H₂O)₄]²⁺ complexes (Healy et al., 1984 ). The en ligand conformation conforms to the crystallographic twofold axis that passes through it. The NDS²⁻ dianion exhibits inversion symmetry, with the inversion center located at the middle point of the C5—C5( $[{3\over 2}]$ − x, $[{3\over 2}]$ − y, $[{3\over 2}]$ − z) bond. The structures of the molecular entities are shown in Fig. 1. Neighboring anions have two distinct orientations relative to the complex cation, with the angle between their planes being 55.06 (7)°. The naphthalene ring system exhibits typical bond lengths and angles, with C—C bond lengths ranging from 1.368 (2) to 1.429 (2) Å, and C—C—C angles within the range 117.98 (18) to 123.08 (15)°.

Figure 1
The structures of the molecular entities in the title salt, showing the atom-labeling scheme and displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius and hydrogen bonds are shown as dashed lines. [Symmetry codes: (i) $[{3\over 2}]$ − x, $[{3\over 2}]$ − y, $[{3\over 2}]$ − z; (ii) $[{3\over 2}]$ − x, y, 1 − z.]

In the crystal, the [Ni(en)(H₂O)₄]²⁺ cation, the NDS²⁻ anion, and the water molecules are associated via classical O—H⋯O and N—H⋯O hydrogen bonds (Table 1). Each [Ni(en)(H₂O)₄]²⁺ cation forms four N—H⋯O and eight O—H⋯O hydrogen bonds with six neighboring organic anions and two water molecules of crystallization. The four aqua and the en ligands in the cation participate exclusively as hydrogen-bonding donor groups (Fig. 2). All six acceptor O atoms of the SO₃⁻ groups of the NDS²⁻ anions participate as double acceptor atoms. It should be noted that the water molecule of crystallization (O3W) is involved in three hydrogen-bonding interactions: two as a donor group with two sulfonate O atoms from two different NDS²⁻ anions as acceptor atoms, and one as an acceptor group for a hydrogen bond with an aqua ligand. Next to Coulombic interactions, these intermolecular interactions connect the molecular building units into the three-dimensional supramolecular structure, as depicted in Fig. 2. As a result of the steric hindrance caused by the sulfonate group, the nearest centroid distance between the naphthalene rings is 6.773 (2) Å. There are four notable C—H⋯π interactions between the methylene groups of the en ligands and the naphthalene rings of the NDS²⁻ anions (Table 1, Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C5/C5′ and C1′–C5′/C5 rings, respectively, where primed atoms are related by the symmetry operation $[{3\over 2}]$ − x, $[{3\over 2}]$ − y, $[{3\over 2}]$ − z.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O1ⁱ	0.85 (1)	1.99 (1)	2.8329 (19)	171 (3)
O1W—H1WB⋯O3W	0.85 (1)	1.85 (1)	2.692 (2)	176 (3)
O2W—H2WA⋯O3ⁱ	0.84 (1)	2.06 (1)	2.8670 (19)	160 (3)
O2W—H2WB⋯O2ⁱⁱ	0.85 (1)	1.99 (1)	2.830 (2)	168 (3)
N1—H1A⋯O3ⁱⁱⁱ	0.88 (1)	2.44 (1)	3.274 (2)	159 (2)
N1—H1B⋯O2^iv	0.89 (1)	2.36 (2)	3.079 (2)	139 (2)
O3W—H3WA⋯O3	0.85 (1)	1.97 (1)	2.794 (2)	164 (3)
O3W—H3WB⋯O1^v	0.84 (1)	2.11 (1)	2.950 (2)	175 (3)
C6—H6A⋯Cg1ⁱⁱⁱ	0.97	2.93	3.755 (2)	143
C6—H6A⋯Cg2^vi	0.97	2.93	3.755 (2)	143
C6—H6B⋯Cg1^vii	0.97	2.88	3.781 (2)	155
C6—H6B⋯Cg2	0.97	2.88	3.781 (2)	155
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) ; (iii) $[-x+{\script{3\over 2}}, y, -z+1]$ ; (iv) $[x+{\script{1\over 2}}, -y+1, z]$ ; (v) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (vii) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
The crystal packing of the title salt in a view along [100]. O—H⋯O and N—H⋯O hydrogen bonds are shown as dashed blue lines, and C—H⋯π interactions as dashed green lines. The coordination polyhedron around Ni^II is given in the polyhedral representation.

Synthesis and crystallization

The commercially available starting materials were used without further purification. Ethane-1,2-diamine (0.06 g, 1.00 mmol) was added slowly to an aqueous solution of NiSO₄·7H₂O (0.28 g, 1.00 mmol), and disodium naphthalene-1,5-disulfonate (0.33 g, 1.00 mmol) was added to the resulting clear deep-blue solution. The resulting solution was set out in an open beaker at room temperature. After 7 d, block-like green crystals were obtained in 60% yield (based on Ni). Elemental analysis calculated (%) for C₁₂H₂₆N₂NiO₁₂S₂: C, 28.09; H, 5.11; N, 5.46; S, 12.50, found: C, 28.01; H, 5.06; N, 5.37; S, 12.43.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Hydrogen atoms attached to nitrogen and those of the water molecules were located in a difference-Fourier map and refined with bond-length restraints of 0.89 (1) and 0.85 (1) Å, respectively.

Table 2
Experimental details

Crystal data
Chemical formula	[Ni(C₂H₈N₂)(H₂O)₄](C₁₀H₆O₆S₂)·2H₂O
M_r	513.18
Crystal system, space group	Monoclinic, I2/a
Temperature (K)	291
a, b, c (Å)	15.4103 (3), 10.1338 (2), 13.4284 (2)
β (°)	108.692 (2)
V (Å³)	1986.44 (7)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	3.99
Crystal size (mm)	0.28 × 0.24 × 0.2

Data collection
Diffractometer	XtaLAB Synergy, Single source at home/near, HyPix3000
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]$ )
T_min, T_max	0.419, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10963, 1926, 1881
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.085, 1.05
No. of reflections	1926
No. of parameters	165
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.33
Computer programs: CrysAlis PRO (Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ), andpubCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2311309

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314623010325/wm4202sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314623010325/wm4202Isup2.hkl

checkCIF report

Computing details top

Tetraaqua(ethane-1,2-diamine-κ²N,N')nickel(II) naphthalene-1,5-disulfonate dihydrate top

Crystal data top

[Ni(C₂H₈N₂)(H₂O)₄](C₁₀H₆O₆S₂)·2H₂O	F(000) = 1072
M_r = 513.18	D_x = 1.716 Mg m⁻³
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54184 Å
a = 15.4103 (3) Å	Cell parameters from 8478 reflections
b = 10.1338 (2) Å	θ = 3.8–71.3°
c = 13.4284 (2) Å	µ = 3.99 mm⁻¹
β = 108.692 (2)°	T = 291 K
V = 1986.44 (7) Å³	Block, light green
Z = 4	0.28 × 0.24 × 0.2 mm

Data collection top

XtaLAB Synergy, Single source at home/near, HyPix3000 diffractometer	1926 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	1881 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.037
Detector resolution: 10.0000 pixels mm^-1	θ_max = 71.5°, θ_min = 3.8°
ω scans	h = −18→18
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	k = −11→12
T_min = 0.419, T_max = 1.000	l = −15→16
10963 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.030	w = 1/[σ²(F_o²) + (0.0539P)² + 1.9301P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.085	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.40 e Å⁻³
1926 reflections	Δρ_min = −0.33 e Å⁻³
165 parameters	Extinction correction: SHELXL (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
8 restraints	Extinction coefficient: 0.00087 (12)

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
Ni1	0.750000	0.31595 (4)	0.500000	0.02364 (16)
O1W	0.66391 (10)	0.16745 (13)	0.51659 (11)	0.0345 (3)
H1WA	0.6474 (19)	0.106 (2)	0.4714 (17)	0.055 (8)*
H1WB	0.6172 (15)	0.191 (3)	0.532 (3)	0.069 (10)*
O2W	0.69189 (10)	0.31220 (13)	0.33422 (11)	0.0341 (3)
H2WA	0.6830 (19)	0.2367 (15)	0.306 (2)	0.051 (7)*
H2WB	0.6401 (11)	0.350 (3)	0.312 (2)	0.059 (8)*
N1	0.83603 (11)	0.46867 (16)	0.48778 (13)	0.0301 (3)
H1A	0.8373 (19)	0.473 (3)	0.4228 (11)	0.048 (7)*
H1B	0.8942 (9)	0.459 (2)	0.5276 (18)	0.050 (7)*
C6	0.80179 (13)	0.59247 (19)	0.52035 (16)	0.0363 (4)
H6A	0.825144	0.667734	0.492234	0.044*
H6B	0.822909	0.599187	0.596421	0.044*
S1	0.57628 (3)	0.54449 (4)	0.76422 (3)	0.02430 (16)
O1	0.59637 (9)	0.54691 (13)	0.87797 (10)	0.0337 (3)
O2	0.47965 (9)	0.56091 (14)	0.70702 (11)	0.0369 (3)
O3	0.61490 (9)	0.42790 (12)	0.73007 (11)	0.0343 (3)
C1	0.63244 (11)	0.68365 (16)	0.73175 (13)	0.0231 (3)
C2	0.57843 (12)	0.78162 (18)	0.67353 (14)	0.0281 (4)
H2	0.514988	0.774290	0.653357	0.034*
C3	0.61849 (12)	0.89311 (18)	0.64417 (14)	0.0301 (4)
H3	0.581294	0.959325	0.604714	0.036*
C4	0.71119 (12)	0.90538 (17)	0.67283 (14)	0.0274 (4)
H4	0.736531	0.979213	0.651599	0.033*
C5	0.76989 (12)	0.80698 (15)	0.73475 (13)	0.0224 (3)
O3W	0.52056 (11)	0.25077 (18)	0.57325 (13)	0.0495 (4)
H3WA	0.540 (2)	0.304 (2)	0.6243 (16)	0.062 (9)*
H3WB	0.485 (2)	0.196 (3)	0.588 (3)	0.076 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0186 (2)	0.0240 (2)	0.0265 (2)	0.000	0.00471 (17)	0.000
O1W	0.0315 (7)	0.0306 (7)	0.0426 (8)	−0.0085 (5)	0.0135 (6)	−0.0048 (6)
O2W	0.0309 (7)	0.0348 (7)	0.0307 (7)	0.0010 (6)	0.0017 (6)	−0.0023 (5)
N1	0.0231 (7)	0.0330 (8)	0.0338 (8)	−0.0030 (6)	0.0086 (6)	0.0004 (6)
C6	0.0348 (11)	0.0275 (9)	0.0436 (10)	−0.0046 (8)	0.0085 (8)	−0.0027 (8)
S1	0.0179 (2)	0.0253 (2)	0.0283 (2)	−0.00158 (14)	0.00546 (17)	0.00269 (14)
O1	0.0335 (7)	0.0381 (7)	0.0309 (7)	0.0009 (5)	0.0123 (6)	0.0064 (5)
O2	0.0184 (7)	0.0412 (7)	0.0459 (8)	−0.0040 (5)	0.0030 (6)	0.0088 (6)
O3	0.0322 (7)	0.0258 (6)	0.0431 (7)	−0.0022 (5)	0.0097 (6)	−0.0036 (5)
C1	0.0185 (8)	0.0247 (8)	0.0249 (8)	−0.0009 (6)	0.0053 (6)	0.0003 (6)
C2	0.0181 (8)	0.0308 (9)	0.0324 (9)	0.0023 (7)	0.0039 (7)	0.0040 (7)
C3	0.0220 (8)	0.0281 (9)	0.0360 (9)	0.0067 (7)	0.0034 (7)	0.0099 (7)
C4	0.0235 (8)	0.0243 (8)	0.0325 (8)	0.0008 (6)	0.0064 (7)	0.0060 (7)
C5	0.0197 (8)	0.0232 (8)	0.0230 (8)	0.0004 (6)	0.0049 (6)	−0.0002 (6)
O3W	0.0438 (9)	0.0612 (10)	0.0485 (9)	−0.0163 (8)	0.0219 (7)	−0.0165 (8)

Geometric parameters (Å, º) top

Ni1—O1Wⁱ	2.0648 (14)	S1—O1	1.4583 (14)
Ni1—O1W	2.0648 (14)	S1—O2	1.4498 (13)
Ni1—O2W	2.1170 (13)	S1—O3	1.4612 (14)
Ni1—O2Wⁱ	2.1170 (13)	S1—C1	1.7803 (17)
Ni1—N1	2.0782 (16)	C1—C2	1.368 (2)
Ni1—N1ⁱ	2.0783 (15)	C1—C5ⁱⁱ	1.429 (2)
O1W—H1WA	0.847 (10)	C2—H2	0.9300
O1W—H1WB	0.846 (10)	C2—C3	1.403 (3)
O2W—H2WA	0.844 (10)	C3—H3	0.9300
O2W—H2WB	0.849 (10)	C3—C4	1.361 (2)
N1—H1A	0.880 (10)	C4—H4	0.9300
N1—H1B	0.889 (10)	C4—C5	1.422 (2)
N1—C6	1.480 (2)	C5—C5ⁱⁱ	1.428 (3)
C6—C6ⁱ	1.512 (4)	O3W—H3WA	0.846 (10)
C6—H6A	0.9700	O3W—H3WB	0.844 (10)
C6—H6B	0.9700

O1Wⁱ—Ni1—O1W	86.43 (8)	N1—C6—H6A	109.9
O1Wⁱ—Ni1—O2W	86.76 (6)	N1—C6—H6B	109.9
O1W—Ni1—O2W	91.75 (6)	C6ⁱ—C6—H6A	109.9
O1Wⁱ—Ni1—O2Wⁱ	91.74 (6)	C6ⁱ—C6—H6B	109.9
O1W—Ni1—O2Wⁱ	86.76 (6)	H6A—C6—H6B	108.3
O1Wⁱ—Ni1—N1	94.94 (6)	O1—S1—O3	111.79 (8)
O1Wⁱ—Ni1—N1ⁱ	178.02 (6)	O1—S1—C1	106.65 (8)
O1W—Ni1—N1	178.02 (6)	O2—S1—O1	112.96 (8)
O1W—Ni1—N1ⁱ	94.94 (6)	O2—S1—O3	112.27 (8)
O2Wⁱ—Ni1—O2W	177.95 (8)	O2—S1—C1	106.06 (8)
N1—Ni1—O2W	89.77 (6)	O3—S1—C1	106.55 (8)
N1—Ni1—O2Wⁱ	91.76 (6)	C2—C1—S1	117.40 (13)
N1ⁱ—Ni1—O2Wⁱ	89.77 (6)	C2—C1—C5ⁱⁱ	121.20 (15)
N1ⁱ—Ni1—O2W	91.77 (6)	C5ⁱⁱ—C1—S1	121.41 (12)
N1—Ni1—N1ⁱ	83.73 (9)	C1—C2—H2	119.9
Ni1—O1W—H1WA	120.8 (19)	C1—C2—C3	120.19 (16)
Ni1—O1W—H1WB	117 (2)	C3—C2—H2	119.9
H1WA—O1W—H1WB	107 (3)	C2—C3—H3	119.6
Ni1—O2W—H2WA	116.0 (19)	C4—C3—C2	120.71 (16)
Ni1—O2W—H2WB	113 (2)	C4—C3—H3	119.6
H2WA—O2W—H2WB	105 (3)	C3—C4—H4	119.5
Ni1—N1—H1A	109.5 (17)	C3—C4—C5	120.97 (16)
Ni1—N1—H1B	114.7 (17)	C5—C4—H4	119.5
H1A—N1—H1B	105 (2)	C4—C5—C1ⁱⁱ	123.08 (15)
C6—N1—Ni1	108.12 (12)	C4—C5—C5ⁱⁱ	118.94 (19)
C6—N1—H1A	112.0 (17)	C5ⁱⁱ—C5—C1ⁱⁱ	117.98 (18)
C6—N1—H1B	107.4 (17)	H3WA—O3W—H3WB	108 (3)
N1—C6—C6ⁱ	109.15 (12)

Ni1—N1—C6—C6ⁱ	−38.8 (2)	O3—S1—C1—C5ⁱⁱ	−53.25 (16)
S1—C1—C2—C3	−179.17 (14)	C1—C2—C3—C4	0.1 (3)
O1—S1—C1—C2	−113.59 (15)	C2—C3—C4—C5	−1.1 (3)
O1—S1—C1—C5ⁱⁱ	66.29 (15)	C3—C4—C5—C1ⁱⁱ	−178.96 (17)
O2—S1—C1—C2	7.07 (16)	C3—C4—C5—C5ⁱⁱ	1.1 (3)
O2—S1—C1—C5ⁱⁱ	−173.05 (14)	C5ⁱⁱ—C1—C2—C3	1.0 (3)
O3—S1—C1—C2	126.87 (14)

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C5/C5' and C1'–C5'/C5 rings, respectively, where primed atoms are related by the symmetry operation 3/2 - x, 3/2 - y, 3/2 - z.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1ⁱⁱⁱ	0.85 (1)	1.99 (1)	2.8329 (19)	171 (3)
O1W—H1WB···O3W	0.85 (1)	1.85 (1)	2.692 (2)	176 (3)
O2W—H2WA···O3ⁱⁱⁱ	0.84 (1)	2.06 (1)	2.8670 (19)	160 (3)
O2W—H2WB···O2^iv	0.85 (1)	1.99 (1)	2.830 (2)	168 (3)
N1—H1A···O3ⁱ	0.88 (1)	2.44 (1)	3.274 (2)	159 (2)
N1—H1B···O2^v	0.89 (1)	2.36 (2)	3.079 (2)	139 (2)
O3W—H3WA···O3	0.85 (1)	1.97 (1)	2.794 (2)	164 (3)
O3W—H3WB···O1^vi	0.84 (1)	2.11 (1)	2.950 (2)	175 (3)
C6—H6A···Cg1ⁱ	0.97	2.93	3.755 (2)	143
C6—H6A···Cg2^vii	0.97	2.93	3.755 (2)	143
C6—H6B···Cg1ⁱⁱ	0.97	2.88	3.781 (2)	155
C6—H6B···Cg2	0.97	2.88	3.781 (2)	155

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

Acknowledgements

The authors thank the Uzbekistan government for direct financial support of this research. A Grant for Fundamental Research from the Center of Science and Technology of Uzbekistan is gratefully acknowledged.

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