research communications
N-[2-(5-methylfuran-2-yl)phenyl]-3-nitro-N-[(3-nitrophenyl)sulfonyl]benzenesulfonamide
and Hirshfeld surface analysis ofaExcellence 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
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 et al., 2019). The electronic and structural properties of the sulfonamide moiety make it a bioisostere of such compounds as urea, thiourea, 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). 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 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).
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 (Safavora2. 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).
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⋯Cg4iv = 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).
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Hirshfeld surfaces were generated for the title molecule using CrystalExplorer17 (Spackman et al., 2021). The dnorm 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%).
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), molecules associate via pairs of N—H⋯N hydrogen bonds, forming a centrosymmetric eight-membered {⋯HNCN}2 synthon. The of OCABUR (space group P21/c) is stabilized by intermolecular C—H⋯O hydrogen bonds. In the crystal of CEGSUE (space group P), 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), molecules are linked into chains parallel to the a axis by intermolecular C—H⋯O hydrogen bonds and π–π stacking interactions. In the 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 (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 (νs SO2), 1352 (br, νas SO2, νs NO2), 1530 (νas 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 . 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 1.2Ueq(C) (1.5 for the methyl groups).
details are summarized in Table 3Supporting information
CCDC reference: 2257159
https://doi.org/10.1107/S2056989023003523/tx2067sup1.cif
contains datablocks I, global. DOI: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
Data collection: CrysAlis PRO (Rigaku OD, 2021); cell
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).C23H17N3O9S2 | F(000) = 1120 |
Mr = 543.52 | Dx = 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 |
Rigaku XtaLAB Synergy Dualflex HyPix diffractometer | 4547 reflections with I > 2σ(I) |
Radiation source: micro-focus sealed X-ray tube | Rint = 0.055 |
φ and ω scans | θmax = 77.8°, θmin = 3.8° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2021) | h = −8→10 |
Tmin = 0.411, Tmax = 0.725 | k = −24→24 |
30531 measured reflections | l = −18→18 |
4812 independent reflections |
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(Fo2) + (0.0588P)2 + 0.9267P] where P = (Fo2 + 2Fc2)/3 |
4812 reflections | (Δ/σ)max = 0.001 |
335 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.50 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 | ||
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* |
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) |
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) |
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. |
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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