research communications
Synthesis and catena-poly[[[aqua{2-[(E)-(1-cyano-2-imino-2-methoxyethylidene)hydrazinyl]benzenesulfonato}sodium]-di-μ-aqua] dihydrate]
ofaCentro 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
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.
CCDC reference: 2257827
1. Chemical context
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). 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, also participate in various types of intermolecular interactions (Polyanskii et al., 2019; Zubkov et al., 2018).
are interesting compounds in the fields of coordination chemistry, crystal engineering, catalysis, molecular recoginition and synthetic organic chemistry (MaHerein, 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.
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).
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 . C-bound H atoms were positioned geometrically (C—H = 0.95 and 0.98 Å) and refined using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(C). O- and N-bound H atoms were located from difference Fourier maps and refined with Uiso(H) = 1.2Ueq(N) and 1.5Ueq(O), with their positions fixed at distances of N—H = 0.93 Å and O—H = 0.85 Å.
details are summarized in Table 2
|
Supporting information
CCDC reference: 2257827
https://doi.org/10.1107/S2056989023003602/wm5680sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023003602/wm5680Isup2.hkl
Data collection: APEX2 (Bruker, 2007); cell
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).[Na(C10H9N4O4S)(H2O)3]·2H2O | F(000) = 824 |
Mr = 394.34 | Dx = 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 |
Bruker APEXII CCD diffractometer | 3389 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.021 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | θmax = 26.5°, θmin = 2.2° |
Tmin = 0.926, Tmax = 0.967 | h = −16→16 |
27710 measured reflections | k = −8→7 |
3748 independent reflections | l = −26→26 |
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(Fo2) + (0.0397P)2 + 0.8377P] where P = (Fo2 + 2Fc2)/3 |
3748 reflections | (Δ/σ)max = 0.001 |
227 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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. |
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···O6iv | 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···O5v | 0.85 | 2.06 | 2.8978 (13) | 171 |
O7—H7B···N4vi | 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···O8vii | 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).
References
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gao, S., Zhu, Z.-B., Huo, L.-H. & Ng, S. W. (2005). Acta Cryst. E61, m279–m281. Web of Science CSD CrossRef IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Gurbanov, A. V., Kuznetsov, M. L., Demukhamedova, S. D., Alieva, I. N., Godjaev, N. M., Zubkov, F. I., Mahmudov, K. T. & Pombeiro, A. J. L. (2020a). CrystEngComm, 22, 628–633. Web of Science CSD CrossRef CAS Google Scholar
Gurbanov, A. V., Kuznetsov, M. L., Karmakar, A., Aliyeva, V. A., Mahmudov, K. T. & Pombeiro, A. J. L. (2022). Dalton Trans. 51, 1019–1031. CSD CrossRef CAS PubMed Google Scholar
Gurbanov, A. V., Kuznetsov, M. L., Mahmudov, K. T., Pombeiro, A. J. L. & Resnati, G. (2020b). Chem. Eur. J. 26, 14833–14837. Web of Science CSD CrossRef CAS PubMed Google Scholar
Hu, M., Du, Y., Li, S., Jiang, Y., Liu, Z. & Geng, C. (2005). Acta Cryst. E61, m15–m17. CrossRef IUCr Journals Google Scholar
Kopylovich, M. N., Mizar, A., Guedes da Silva, M. F. C., Mac Leod, T. C. O., Mahmudov, K. T. & Pombeiro, A. J. L. (2013). Chem. Eur. J. 19, 588–600. CrossRef CAS PubMed Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Ma, Z., Mahmudov, K. T., Aliyeva, V. A., Gurbanov, A. V., Guedes da Silva, M. F. C. & Pombeiro, A. J. L. (2021). Coord. Chem. Rev. 437, 213859. Web of Science CrossRef Google Scholar
Maharramov, A. M., Aliyeva, R. A., Aliyev, I. A., Pashaev, F. G., Gasanov, A. G., Azimova, S. I., Askerov, R. K., Kurbanov, A. V. & Mahmudov, K. T. (2010). Dyes Pigments, 85, 1–6. Web of Science CSD CrossRef CAS Google Scholar
Mahmoudi, G., Dey, L., Chowdhury, H., Bauzá, A., Ghosh, B. K., Kirillov, A. M., Seth, S. K., Gurbanov, A. V. & Frontera, A. (2017a). Inorg. Chim. Acta, 461, 192–205. Web of Science CSD CrossRef CAS Google Scholar
Mahmoudi, G., Khandar, A. A., Afkhami, F. A., Miroslaw, B., Gurbanov, A. V., Zubkov, F. I., Kennedy, A., Franconetti, A. & Frontera, A. (2019). CrystEngComm, 21, 108–117. Web of Science CSD CrossRef CAS Google Scholar
Mahmoudi, G., Zaręba, J. K., Gurbanov, A. V., Bauzá, A., Zubkov, F. I., Kubicki, M., Stilinović, V., Kinzhybalo, V. & Frontera, A. (2017b). Eur. J. Inorg. Chem. 2017, 4763–4772. CSD CrossRef CAS Google Scholar
Mahmudov, K. T., Guedes da Silva, M. F. C., Glucini, M., Renzi, M., Gabriel, K. C. P., Kopylovich, M. N., Sutradhar, M., Marchetti, F., Pettinari, C., Zamponi, S. & Pombeiro, A. J. L. (2012). Inorg. Chem. Commun. 22, 187–189. Web of Science CSD CrossRef CAS Google Scholar
Mahmudov, K. T., Gurbanov, A. V., Aliyeva, V. A., Guedes da Silva, M. F. C., Resnati, G. & Pombeiro, A. J. L. (2022). Coord. Chem. Rev. 464, 214556. Web of Science CrossRef Google Scholar
Mahmudov, K. T., Kopylovich, M. N. & Pombeiro, A. J. L. (2013). Coord. Chem. Rev. 257, 1244–1281. Web of Science CrossRef CAS Google Scholar
Mahmudov, K. T., Maharramov, A. M., Aliyeva, R. A., Aliyev, I. A., Askerov, R. K., Batmaz, R., Kopylovich, M. N. & Pombeiro, A. J. L. (2011). J. Photochem. Photobiol. Chem. 219, 159–165. Web of Science CSD CrossRef CAS Google Scholar
Mahmudov, K. T., Maharramov, A. M., Aliyeva, R. A., Aliyev, I. A., Kopylovich, M. N. & Pombeiro, A. J. L. (2010). Anal. Lett. 43, 2923–2938. Web of Science CrossRef CAS Google Scholar
Polyanskii, K. B., Alekseeva, K. A., Raspertov, P. V., Kumandin, P. A., Nikitina, E. V., Gurbanov, A. V. & Zubkov, F. I. (2019). Beilstein J. Org. Chem. 15, 769–779. CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Zubkov, F. I., Mertsalov, D. F., Zaytsev, V. P., Varlamov, A. V., Gurbanov, A. V., Dorovatovskii, P. V., Timofeeva, T. V., Khrustalev, V. N. & Mahmudov, K. T. (2018). J. Mol. Liq. 249, 949–952. Web of Science CSD CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.