research communications
(E,E)-3-Methyl-2,5-bis(4-methylbenzylidene)cyclopentanone: synthesis, characterization, Hirshfeld surface analysis and antibacterial activity
aLaboratoire des Sciences Analytiques, Matériaux et Environnement (LSAME), Université Larbi Ben M'hidi, Oum El Bouaghi, 04000, Algeria, bDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Larbi Ben M'hidi, Oum El Bouaghi, 04000, Algeria, and cUniversité de Rennes 1, Institut des Sciences Chimiques de Rennes, CNRS UMR, 6226, Avenue du Général Leclerc, 35042 Rennes Cedex, France
*Correspondence e-mail: wbouchene@yahoo.fr
The title compound, (E,E)-3-methyl-2,5-bis(4-methylbenzylidene)cyclopentanone (MBMCP), C22H22O, was obtained by Claisen–Schmidt condensation of 4-methylbenzaldehyde with 3-methylcyclopentanone in good yield. The structure of MBMCP was studied using UV, FT–IR and Raman spectroscopy, single-crystal X-ray diffraction (XRD) measurements, and 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. The molecular structure of MBMCP is fully extended in the E,E configuration. C—H⋯π stacking interactions play a significant role in the stabilization of the molecular packing. Hirshfeld surface analysis was used to quantify the non-covalent interactions in the Microbiological studies were performed to investigate the antimicrobial activity of this new product.
Keywords: Claisen–Schmidt reaction; crossed-aldol condensation; crystal structure; spectroscopic studies.
CCDC reference: 1515960
1. Chemical context
The Claisen–Schmidt reaction has great importance in the synthesis of organic compounds (Rajput & Kaur, 2012), in particular in the synthesis of bis(substituted-benzylidene)cycloalkanones. This reaction is catalysed using strong acids (Dhar & Barton, 1981; Gall et al., 1999) and base with or without solvents (Geissman & Clinton, 1946; Shan et al., 2010). Recently, animal bone meal was used as a catalyst for crossed-aldol condensation (Riadi et al., 2010). The preparation of β-chloro, β-bromo and α,β-unsaturated from β-diketones has been carried out using Vilsmeier reagents (Mewshaw et al., 1989). Numerous α,α′-bis(substituted-benzylidene)cycloalkanones exhibit biological activities (Robinson et al., 2005; Piantadosi et al., 1973). Furthermore, they are used as precursors for the preparation of biologically active such as pyrimidines (Deli et al., 1984; Guilford et al., 1999) and pyrazolines (Ziani et al., 2013). These compounds have received a lot of attention because of their uses as perfume intermediates, pharmaceutical, agrochemical and units (Artico et al., 1998; Amoozadeh et al., 2010). α,α′-Bis(substituted-benzylidene)cycloalkanones are also essential pharmacophores of various natural products (Shetty et al., 2015). An example of permitted therapeutic agents including this molecular framework is coumarin-chalcone (anticancer agents).
In the present work, we have synthesized, in one-step, (E,E)-3-methyl-2,5-bis(4-methylbenzylidene)cyclopentanone (MBMCP) by NaOH-catalysed Claisen–Schmidt condensation of 4-methyl benzaldehyde with 3-methyl cyclopentanone (see scheme). The structure of MBMCP was investigated by UV, FT–IR and Raman spectroscopy, single crystal X-ray diffraction (XRD) measurements and 1H and 13C nuclear magnetic resonance (NMR) spectroscopy.
Several studies on the biological activity of unsaturated et al. (2018). The antibacterial activities of these against drug-sensitive bacteria, including Staphylococcus aureus, Enterococcus faecalis, Escherichia coli and Salmonella enterica indicate that these compounds have potential therapeutic effects against bacterial infections. The phenyl group and the fluoride atom in these compounds were found to play an important role in their antibacterial and hemolytic activities. The above findings prompted us to evaluate the antibacterial activity of MBMCP in vitro against four bacterial strains.
have been carried out. As an example, a series of chalcone derivatives that mimic the essential properties of cationic antimicrobial were designed and synthesized by Chu2. Structural commentary
The structure of MBMCP was confirmed using single X-ray diffraction. The with the atom-numbering scheme. The cyclopentanone ring adopts a half-chair form, with deviations of −0.146 (2) and 0.160 (2) Å from the mean plane of the ring for C13 and C14, respectively. The torsion angles within the five-membered ring are 4.7 (2) (C9—C10—C12—C13), −19.5 (2)° (C10—C12—C13—C14) and 26.3 (2)° (C12—C13—C14—C9), confirming the non-planarity of the central ring. The C15 methyl group in MBMCP lies practically perpendicular to the plane of its attached cyclopentanone ring, with torsion angle C12—C13—C14—C15 of −91.4 (2)°. The mean planes of the phenyl rings at either end of the molecule are twisted with respect to one another by 41.3 (1)°.
comprised a single molecule, illustrated in Fig. 1The C8=C9 and C12=C16 bond lengths are 1.344 (3) and 1.335 (3) Å, respectively, and those for C8—C5 and C16—C17 are 1.464 (3) and 1.462 (3) Å, respectively. These values are in between the normal values for single and double bonds (1.54 and 1.33 Å, respectively), which is consistent with a delocalized π-bonding system.
The molecular structure of MBMCP is fully extended in the E,E configuration stabilized by two short intramolecular contacts, H8⋯O11 and H16⋯O11 (2.55 and 2.53 Å, respectively).
3. Spectroscopic results
The FT–IR spectrum of MBMCP shows the strong band of a conjugated carbonyl group at 1670 cm−1 and two bands at 1616 and at 1596 cm−1 for the two non-equivalent exo-cyclic C=C bonds. The Raman spectrum shows two characteristic bands in the 1720–1670 and 1620–1590 cm−1 regions, which indicate the presence of carbonyl groups conjugated with the double bonds.
The above result is also confirmed using the chemical shifts in the 13C NMR spectrum for the carbonyl groups (196.46 ppm) and of the C=C group at (139.7 and 139.8 ppm). The dienone of cyclic ketone derivatives occur in E,E, Z,Z, or Z,E configurations (Vatsadze et al., 2006) and we have obtained the E,E isomer. The 1H NMR spectrum shows the signals of CH protons at a greater field than 7.2 ppm (δ = 7.51–7.53 ppm), which is in agreement with the E isomers, whereas the signals for the Z isomers are identified using the chemical shifts at δ ∼6.8 ppm (George & Roth, 1971).
The UV spectrum of the designated compound in ethanol reveals four absorption bands at 208 nm (∊ = 3.215 L mol−1cm−1), 237 nm (∊ = 1.984 L mol−1cm−1), 364 nm (∊ = 3.215 L mol−1cm−1) and 376 nm (∊ = 2.436 L mol−1cm−1) assigned to n–π, π–π* transitions.
4. Supramolecular features
Molecules of MBMCP pack with no classical hydrogen bonds. However, C18—H18⋯O11(1 − x, −y,1 − z) and C23—H23B⋯O11( + x, − y, + z) short contacts occur, where the oxygen atom of the carbonyl group works as an acceptor with O11⋯H distances of 2.61 and 2.66 Å, respectively. These interactions are neglected as the H⋯O van der Waals distance is 2.60 Å and C—H⋯O contacts frequently have H⋯O separations shorter than 2.4 Å (Taylor & Kennard, 1982). On the other hand, even though the carbonyl group is a strong acceptor, the O atom acts as a multiple acceptor. This condition corresponds to an important argument for the structural importance of the C—H⋯O hydrogen bond (Steiner, 1996).
Molecular chains of MBMCP propagate along the [101] direction through a C—H⋯π interaction (Table 1) involving the C4–H4 group of the C2–C7 phenyl ring pointing towards the π cloud on an adjacent C17–C22 ring, as shown in Fig. 2. The contact distances are consistent with those of the C—H⋯π edge-to-face interactions observed in the of benzene (Bacon et al., 1964).
The molecules of MBMCP stack in waves along the a-axis direction, as shown in Fig. 3. The methyl carbon (C1) makes an important contribution to the stability of this stacking arrangement via the establishment of a C—H⋯π interaction with the centroid of a neighboring aryl ring.
5. Hirshfeld surface analysis
The intermolecular interactions were quantified using Hirshfeld surface analysis (Fig. 4). The Hirshfeld surfaces of MBMCP, their associated two-dimensional fingerprint plots and relative contributions to the Hirshfeld surface area from the various close intermolecular contacts were calculated using CrystalExplorer software (Wolff et al., 2007). The analysis of intermolecular interactions through the mapping of dnorm compares the contact distances di and de from the Hirshfeld surface to the nearest atom inside and outside, respectively, with their respective van der Waals radii. The red regions represent contacts shorter than the sum of van der Waals radii, white regions represent intermolecular distances equal to van der Waals contacts and blue regions represent contacts longer than van der Waals radii.
As expected in organic compounds, the shortest and most abundant contacts for MBMCP are the H⋯H intermolecular interactions with a contribution to the Hirshfeld surface of 58%. The C⋯H contacts, which refer to the C—H⋯π interactions described previously, contribute 32.2% of the Hirshfeld surfaces. On the shape-index surface, the C—H⋯π interactions are clearly observed as red regions over the aromatic rings. The shape-index is in agreement with the 2D fingerprint plot, in which these interactions appear as two broad spikes both having de + di ∼2.7 Å (Fig. 5). The large flat region, delineated by a blue outline on the curvedness of MBMCP reveals that π–π stacking interactions are absent.
6. Antibacterial activity
The antibacterial activity of MBMCP was assayed in vitro against Escherchia coli, Staphyococcus aureus, Salmonella typhi and Bacillus subtilis via an agar cup-plate diffusion method (Barry, 1976; Ponce et al., 2003). The bacteria tests were sub-cultured in Mueller–Hinton broth, from which 1 mL of cell suspension was taken and the was adjusted to 0.5. The suspension was then spread as a thin film over the Mueller–Hinton agar plates. The synthetic compound was loaded onto discs with concentrations of 0.2, 0.3, 0.4 and 0.5 µg mL−1 and air-dried. The dry discs were placed on the inoculated Mueller–Hinton agar plates and incubated at 310 K for 48 h. A penicillin disc (10 µg per disc) was used as the standard. A disc of 150 µl of DMSO served as the control. After incubation, the zone of inhibition (in mm) was measured and compared with that of penicillin for each concentration.
The antibacterial screening results are collected in Table 2. They reveal that the produced compound shows an antibacterial activity at MIC = 0.5 µg mL−1 towards all the bacterial strains, but differs from one strain to another when comparing the zones of inhibition (mm). It exhibits moderate and promising activities against Staphylococcus aureus (27 mm) and Bacillus subtilis (14 mm). However, it shows low activities against Escherchia coli (7 mm) and Salmonella typhi (12 mm), which probably demonstrate that the produced compound exhibits a specific effect on those microorganisms.
7. Database survey
A search of the Cambridge Structural Database, CSD (Version 5.38; ConQuest 1.19; Groom et al., 2016) revealed 20 derivatives of bis(benzylidene)cyclopentanone. The variety of compounds reported in the literature (Kawamata et al., 1998; Nakhaei et al., 2017) is due to substitution on the phenyl rings and/or on the cyclopentanone by different functional groups, such as hydroxy, methoxy, chlorine, fluorine etc., and also by radicals. Cyclic conjugated bis(benzylidene)ketones have been reported to exhibit potent anti-inflammatory, antibacterial and antioxidant activity (Shetty et al., 2015). E,E-2,5-dibenzylidene-3-methylcyclopentanone (DBMCP) is the nearest analogue to MBMCP. This molecule, like that of the title compound, exhibits a twisted five-membered ring, conveying modest non-planarity to the overall molecular shape with a maximum deviation from the mean plane of 0.44 Å (Theocharis et al., 1984). The basic skeleton of this compound family, E,E-2,5-dibenzylidenecyclopentanone (DBCP), has been isolated in two polymorphic forms, exhibiting two different but nearly superimposable conformations (Arshad et al., 2014). The previously reported polymorph I crystallizes in the orthorhombic C2221 (Theocharis et al., 1984), while the second form crystallizes in the monoclinic P21 Both forms pack as supramolecular chains mainly stabilized by C—H⋯O, π–π and C—H⋯π interactions and forming sheet-like multilayered structures.
8. Synthesis and crystallization
A mixture of 4-methylbenzaldehyde (20 mmol, 2 eq.) and 3-methylcyclopentanone (10 mmol, 1 eq.) were dissolved in ethanol (15 mL) into a flask (simple necked, round bottomed), and the solution was stirred for a few minutes at 273 K (ice bath). A solution of NaOH (10 mL, 40%) was added dropwise over several minutes into this mixture. The resulting mixture was stirred for 4 h approximately at room temperature. The obtained yellow precipitate was then filtered, washed with HCl (0.1 N) and cold water and then dried. The pure product was crystallized from ethanol solution at room temperature in 75% yield. Single crystals for X-ray diffraction were grown by slow solvent evaporation from a solution in ethanol.
The FT–IR spectrum of the compound was measured by the KBr pellet technique in the range of 4000–400 cm−1, with a Nexus Nicolet FT–IR spectrometer at a resolution of 2 cm−1. A Bruker Optik GmbH system was utilized to measure the Raman spectrum of the powder compound. A class 4 laser Raman spectrometer of 532 nm excitation from a (3B) was used with 2 cm−1 resolution within the spectroscopic range 3500–0 cm−1. 1H and 13C NMR spectra were quantified with CDCl3 using a (400.13 MHz in 1H) Avance 400 Bruker spectrometer with TMS as internal standard.
1H NMR (400 MHz, CDCl3) δ (ppm): 1.23 (d, 1H, CH3), 1.54 (s, 2H, H2O), 2.39 (s, 6H, 2CH3), 2.76 (dd, 1Hcycle), 3.18 (ddd, 1Hcycle), 3.66 (m, 1Hcycle), 7.22 (d, 2Haryl), 7.25 (d, 2Haryl), 7.47 (d, 3Haryl), 7.51 (s, 1Hethylenic), 7.53 (s, 1Hethylenic), and 7.66 (t, 1Haryl).
13C NMR (75.46 MHz, CDCl3) δ (ppm): 21.03 (CH3), 23.47 (CH3), 23.49 (CH3), 32.01 (CHcycle), 35.98 (CH2cycle), 129.51 (2C—Ar), 129.62 (2C—Ar), 130.71 (2C—Ar), 130.79 (2C—Ar), 133.37 (2C—Ar), 134.38 (2C—Ar), 135.57 (CH=Ccycle), 139.72 (Ccycle=CH), 139.76 (Ccycle=CH), 142.51 (CH=Ccycle), and 196.46 (C=O).
Fourier–transform infrared (FT–IR) spectroscopy (KBr, cm−1): 3056–3022 (CH aromatic), 2863 (CH alyphatic), 1670 (C=O), 1616 and 1596 (C=C), and 1590.90, 1545.45 (C=C of aromatic rings).
Raman spectroscopy with 1000–1670 Hz frequency range for the C—C, C=C and C=O bonds. In addition, 2800–3156 Hz frequency domain for C—H bonds. Ultraviolet (UV) spectroscopy [EtOH, λ (nm)]: 208, 237 assignable to π–π, and 364, 376 assignable to π–π* transitions.
9. Refinement
Crystal data, data collection and structure . H atoms were included in their calculated positions and refined using the riding-atom approximation: C—H = 0.96 Å (methyl CH3) and 0.93 Å (aryl), with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for all other H atoms.
details are summarized in Table 3
|
Supporting information
CCDC reference: 1515960
https://doi.org/10.1107/S2056989019003827/fy2134sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019003827/fy2134Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989019003827/fy2134Isup3.cml
Data collection: SAINT (Bruker, 2014); cell
APEX3 (Bruker, 2015) and SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: CRYSCALc (T. Roisnel, local program, version of 2015).C22H22O | F(000) = 648 |
Mr = 302.39 | Dx = 1.207 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8037 (9) Å | Cell parameters from 2848 reflections |
b = 8.9815 (9) Å | θ = 2.4–27.4° |
c = 18.8946 (17) Å | µ = 0.07 mm−1 |
β = 90.985 (4)° | T = 150 K |
V = 1663.5 (3) Å3 | Thick plate, colourless |
Z = 4 | 0.52 × 0.28 × 0.06 mm |
Bruker D8 VENTURE diffractometer | 3808 independent reflections |
Radiation source: Incoatec microfocus sealed tube | 2471 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.115 |
rotation images scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −12→12 |
Tmin = 0.735, Tmax = 0.996 | k = −11→10 |
15325 measured reflections | l = −24→24 |
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)] = 0.070 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.171 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0652P)2 + 0.431P] where P = (Fo2 + 2Fc2)/3 |
3808 reflections | (Δ/σ)max = 0.005 |
211 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.26 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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6385 (3) | 0.4045 (3) | −0.09361 (12) | 0.0385 (6) | |
H1A | 0.6054 | 0.3291 | −0.1273 | 0.058* | |
H1B | 0.7347 | 0.4259 | −0.1025 | 0.058* | |
H1C | 0.5848 | 0.4958 | −0.0994 | 0.058* | |
C2 | 0.6242 (2) | 0.3472 (3) | −0.01957 (12) | 0.0274 (5) | |
C3 | 0.5158 (2) | 0.2568 (3) | −0.00074 (13) | 0.0357 (6) | |
H3 | 0.4503 | 0.2287 | −0.0359 | 0.043* | |
C4 | 0.5009 (2) | 0.2070 (3) | 0.06766 (12) | 0.0316 (6) | |
H4 | 0.4260 | 0.1443 | 0.0785 | 0.038* | |
C5 | 0.5940 (2) | 0.2468 (2) | 0.12164 (11) | 0.0227 (5) | |
C6 | 0.7056 (2) | 0.3345 (3) | 0.10266 (12) | 0.0286 (5) | |
H6 | 0.7722 | 0.3611 | 0.1375 | 0.034* | |
C7 | 0.7195 (2) | 0.3824 (3) | 0.03386 (12) | 0.0308 (6) | |
H7 | 0.7964 | 0.4414 | 0.0223 | 0.037* | |
C8 | 0.5659 (2) | 0.1961 (3) | 0.19360 (12) | 0.0242 (5) | |
H8 | 0.4994 | 0.1195 | 0.1962 | 0.029* | |
C9 | 0.6180 (2) | 0.2391 (2) | 0.25660 (12) | 0.0226 (5) | |
C10 | 0.5636 (2) | 0.1772 (2) | 0.32316 (12) | 0.0232 (5) | |
O11 | 0.49025 (16) | 0.06702 (19) | 0.32852 (8) | 0.0328 (4) | |
C12 | 0.6133 (2) | 0.2716 (2) | 0.38293 (12) | 0.0228 (5) | |
C13 | 0.6898 (2) | 0.4010 (2) | 0.35203 (11) | 0.0244 (5) | |
H13A | 0.7731 | 0.4227 | 0.3805 | 0.029* | |
H13B | 0.6318 | 0.4913 | 0.3506 | 0.029* | |
C14 | 0.7269 (2) | 0.3520 (2) | 0.27653 (12) | 0.0235 (5) | |
H14 | 0.7247 | 0.4386 | 0.2433 | 0.028* | |
C15 | 0.8679 (2) | 0.2773 (3) | 0.27741 (13) | 0.0315 (6) | |
H15A | 0.8700 | 0.1980 | 0.3130 | 0.047* | |
H15B | 0.9381 | 0.3515 | 0.2891 | 0.047* | |
H15C | 0.8856 | 0.2349 | 0.2307 | 0.047* | |
C16 | 0.5869 (2) | 0.2357 (2) | 0.44987 (11) | 0.0236 (5) | |
H16 | 0.5378 | 0.1453 | 0.4553 | 0.028* | |
C17 | 0.6207 (2) | 0.3119 (2) | 0.51624 (11) | 0.0230 (5) | |
C18 | 0.6069 (2) | 0.2345 (3) | 0.57982 (12) | 0.0262 (5) | |
H18 | 0.5783 | 0.1335 | 0.5787 | 0.031* | |
C19 | 0.6338 (2) | 0.3014 (3) | 0.64411 (12) | 0.0288 (6) | |
H19 | 0.6255 | 0.2451 | 0.6864 | 0.035* | |
C20 | 0.6730 (2) | 0.4508 (3) | 0.64823 (12) | 0.0269 (5) | |
C21 | 0.6866 (2) | 0.5284 (3) | 0.58517 (12) | 0.0274 (5) | |
H21 | 0.7138 | 0.6299 | 0.5866 | 0.033* | |
C22 | 0.6614 (2) | 0.4612 (3) | 0.52014 (12) | 0.0247 (5) | |
H22 | 0.6718 | 0.5170 | 0.4779 | 0.030* | |
C23 | 0.6981 (3) | 0.5255 (3) | 0.71853 (13) | 0.0394 (7) | |
H23A | 0.7168 | 0.6314 | 0.7110 | 0.059* | |
H23B | 0.7766 | 0.4790 | 0.7425 | 0.059* | |
H23C | 0.6172 | 0.5147 | 0.7478 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0416 (15) | 0.0411 (16) | 0.0330 (14) | −0.0006 (12) | 0.0010 (11) | 0.0032 (12) |
C2 | 0.0267 (12) | 0.0281 (13) | 0.0273 (12) | 0.0035 (10) | 0.0014 (10) | −0.0004 (10) |
C3 | 0.0260 (12) | 0.0494 (17) | 0.0314 (14) | −0.0082 (11) | −0.0056 (10) | −0.0007 (12) |
C4 | 0.0218 (12) | 0.0392 (15) | 0.0338 (14) | −0.0112 (10) | 0.0002 (10) | −0.0009 (11) |
C5 | 0.0189 (10) | 0.0199 (11) | 0.0293 (12) | 0.0013 (9) | 0.0013 (9) | 0.0003 (9) |
C6 | 0.0218 (11) | 0.0329 (14) | 0.0309 (13) | −0.0075 (10) | −0.0032 (9) | −0.0017 (11) |
C7 | 0.0279 (12) | 0.0310 (14) | 0.0337 (13) | −0.0112 (10) | 0.0049 (10) | 0.0000 (11) |
C8 | 0.0168 (10) | 0.0214 (12) | 0.0346 (13) | 0.0001 (9) | 0.0000 (9) | 0.0012 (10) |
C9 | 0.0180 (10) | 0.0180 (11) | 0.0318 (12) | 0.0041 (8) | 0.0001 (9) | 0.0022 (10) |
C10 | 0.0198 (11) | 0.0198 (11) | 0.0299 (12) | 0.0018 (9) | −0.0011 (9) | 0.0049 (10) |
O11 | 0.0343 (9) | 0.0284 (9) | 0.0357 (10) | −0.0127 (8) | −0.0001 (7) | 0.0056 (8) |
C12 | 0.0191 (10) | 0.0178 (11) | 0.0314 (12) | 0.0040 (8) | −0.0008 (9) | 0.0037 (10) |
C13 | 0.0240 (11) | 0.0192 (12) | 0.0298 (12) | −0.0016 (9) | −0.0013 (9) | 0.0019 (10) |
C14 | 0.0202 (11) | 0.0203 (12) | 0.0299 (12) | −0.0027 (9) | 0.0016 (9) | 0.0031 (10) |
C15 | 0.0212 (11) | 0.0354 (15) | 0.0380 (14) | −0.0036 (10) | −0.0009 (10) | −0.0031 (11) |
C16 | 0.0205 (11) | 0.0180 (11) | 0.0323 (13) | 0.0033 (9) | 0.0017 (9) | 0.0041 (10) |
C17 | 0.0168 (10) | 0.0234 (12) | 0.0289 (12) | 0.0040 (9) | 0.0029 (9) | 0.0053 (10) |
C18 | 0.0208 (11) | 0.0248 (13) | 0.0331 (13) | 0.0035 (9) | 0.0032 (9) | 0.0065 (10) |
C19 | 0.0222 (11) | 0.0374 (14) | 0.0271 (13) | 0.0108 (10) | 0.0050 (9) | 0.0104 (11) |
C20 | 0.0164 (10) | 0.0387 (14) | 0.0258 (12) | 0.0111 (10) | 0.0011 (9) | −0.0002 (11) |
C21 | 0.0223 (11) | 0.0247 (13) | 0.0352 (14) | 0.0049 (9) | 0.0017 (10) | 0.0018 (10) |
C22 | 0.0227 (11) | 0.0263 (13) | 0.0252 (12) | 0.0043 (9) | 0.0005 (9) | 0.0061 (10) |
C23 | 0.0380 (14) | 0.0501 (17) | 0.0302 (14) | 0.0100 (12) | 0.0005 (11) | −0.0021 (12) |
C1—C2 | 1.499 (3) | C13—H13A | 0.9900 |
C1—H1A | 0.9800 | C13—H13B | 0.9900 |
C1—H1B | 0.9800 | C14—C15 | 1.536 (3) |
C1—H1C | 0.9800 | C14—H14 | 1.0000 |
C2—C3 | 1.388 (3) | C15—H15A | 0.9800 |
C2—C7 | 1.400 (3) | C15—H15B | 0.9800 |
C3—C4 | 1.378 (3) | C15—H15C | 0.9800 |
C3—H3 | 0.9500 | C16—C17 | 1.462 (3) |
C4—C5 | 1.404 (3) | C16—H16 | 0.9500 |
C4—H4 | 0.9500 | C17—C18 | 1.396 (3) |
C5—C6 | 1.399 (3) | C17—C22 | 1.401 (3) |
C5—C8 | 1.464 (3) | C18—C19 | 1.377 (3) |
C6—C7 | 1.379 (3) | C18—H18 | 0.9500 |
C6—H6 | 0.9500 | C19—C20 | 1.398 (4) |
C7—H7 | 0.9500 | C19—H19 | 0.9500 |
C8—C9 | 1.344 (3) | C20—C21 | 1.389 (3) |
C8—H8 | 0.9500 | C20—C23 | 1.504 (3) |
C9—C10 | 1.483 (3) | C21—C22 | 1.387 (3) |
C9—C14 | 1.515 (3) | C21—H21 | 0.9500 |
C10—O11 | 1.228 (3) | C22—H22 | 0.9500 |
C10—C12 | 1.488 (3) | C23—H23A | 0.9800 |
C12—C16 | 1.335 (3) | C23—H23B | 0.9800 |
C12—C13 | 1.506 (3) | C23—H23C | 0.9800 |
C13—C14 | 1.543 (3) | ||
C2—C1—H1A | 109.5 | H13A—C13—H13B | 108.8 |
C2—C1—H1B | 109.5 | C9—C14—C15 | 109.94 (18) |
H1A—C1—H1B | 109.5 | C9—C14—C13 | 104.13 (17) |
C2—C1—H1C | 109.5 | C15—C14—C13 | 109.97 (18) |
H1A—C1—H1C | 109.5 | C9—C14—H14 | 110.9 |
H1B—C1—H1C | 109.5 | C15—C14—H14 | 110.9 |
C3—C2—C7 | 116.8 (2) | C13—C14—H14 | 110.9 |
C3—C2—C1 | 121.6 (2) | C14—C15—H15A | 109.5 |
C7—C2—C1 | 121.6 (2) | C14—C15—H15B | 109.5 |
C4—C3—C2 | 121.6 (2) | H15A—C15—H15B | 109.5 |
C4—C3—H3 | 119.2 | C14—C15—H15C | 109.5 |
C2—C3—H3 | 119.2 | H15A—C15—H15C | 109.5 |
C3—C4—C5 | 121.4 (2) | H15B—C15—H15C | 109.5 |
C3—C4—H4 | 119.3 | C12—C16—C17 | 130.9 (2) |
C5—C4—H4 | 119.3 | C12—C16—H16 | 114.6 |
C6—C5—C4 | 117.3 (2) | C17—C16—H16 | 114.6 |
C6—C5—C8 | 125.0 (2) | C18—C17—C22 | 117.6 (2) |
C4—C5—C8 | 117.7 (2) | C18—C17—C16 | 118.7 (2) |
C7—C6—C5 | 120.5 (2) | C22—C17—C16 | 123.6 (2) |
C7—C6—H6 | 119.7 | C19—C18—C17 | 121.5 (2) |
C5—C6—H6 | 119.7 | C19—C18—H18 | 119.3 |
C6—C7—C2 | 122.3 (2) | C17—C18—H18 | 119.3 |
C6—C7—H7 | 118.9 | C18—C19—C20 | 121.1 (2) |
C2—C7—H7 | 118.9 | C18—C19—H19 | 119.5 |
C9—C8—C5 | 131.2 (2) | C20—C19—H19 | 119.5 |
C9—C8—H8 | 114.4 | C21—C20—C19 | 117.7 (2) |
C5—C8—H8 | 114.4 | C21—C20—C23 | 121.1 (2) |
C8—C9—C10 | 120.4 (2) | C19—C20—C23 | 121.2 (2) |
C8—C9—C14 | 131.9 (2) | C22—C21—C20 | 121.6 (2) |
C10—C9—C14 | 107.62 (18) | C22—C21—H21 | 119.2 |
O11—C10—C9 | 126.3 (2) | C20—C21—H21 | 119.2 |
O11—C10—C12 | 125.5 (2) | C21—C22—C17 | 120.6 (2) |
C9—C10—C12 | 108.17 (19) | C21—C22—H22 | 119.7 |
C16—C12—C10 | 121.0 (2) | C17—C22—H22 | 119.7 |
C16—C12—C13 | 131.3 (2) | C20—C23—H23A | 109.5 |
C10—C12—C13 | 107.73 (18) | C20—C23—H23B | 109.5 |
C12—C13—C14 | 105.37 (18) | H23A—C23—H23B | 109.5 |
C12—C13—H13A | 110.7 | C20—C23—H23C | 109.5 |
C14—C13—H13A | 110.7 | H23A—C23—H23C | 109.5 |
C12—C13—H13B | 110.7 | H23B—C23—H23C | 109.5 |
C14—C13—H13B | 110.7 | ||
C7—C2—C3—C4 | 1.4 (4) | C16—C12—C13—C14 | 160.9 (2) |
C1—C2—C3—C4 | −178.5 (2) | C10—C12—C13—C14 | −19.5 (2) |
C2—C3—C4—C5 | 0.8 (4) | C8—C9—C14—C15 | −88.7 (3) |
C3—C4—C5—C6 | −2.4 (4) | C10—C9—C14—C15 | 93.9 (2) |
C3—C4—C5—C8 | 176.5 (2) | C8—C9—C14—C13 | 153.5 (2) |
C4—C5—C6—C7 | 1.9 (3) | C10—C9—C14—C13 | −23.9 (2) |
C8—C5—C6—C7 | −176.9 (2) | C12—C13—C14—C9 | 26.3 (2) |
C5—C6—C7—C2 | 0.3 (4) | C12—C13—C14—C15 | −91.4 (2) |
C3—C2—C7—C6 | −2.0 (4) | C10—C12—C16—C17 | −178.0 (2) |
C1—C2—C7—C6 | 178.0 (2) | C13—C12—C16—C17 | 1.6 (4) |
C6—C5—C8—C9 | 13.9 (4) | C12—C16—C17—C18 | −166.3 (2) |
C4—C5—C8—C9 | −164.9 (2) | C12—C16—C17—C22 | 16.4 (4) |
C5—C8—C9—C10 | 175.1 (2) | C22—C17—C18—C19 | −0.8 (3) |
C5—C8—C9—C14 | −2.0 (4) | C16—C17—C18—C19 | −178.30 (19) |
C8—C9—C10—O11 | 14.6 (3) | C17—C18—C19—C20 | 1.5 (3) |
C14—C9—C10—O11 | −167.6 (2) | C18—C19—C20—C21 | −1.3 (3) |
C8—C9—C10—C12 | −165.43 (19) | C18—C19—C20—C23 | 178.0 (2) |
C14—C9—C10—C12 | 12.3 (2) | C19—C20—C21—C22 | 0.4 (3) |
O11—C10—C12—C16 | 4.3 (3) | C23—C20—C21—C22 | −178.8 (2) |
C9—C10—C12—C16 | −175.62 (19) | C20—C21—C22—C17 | 0.2 (3) |
O11—C10—C12—C13 | −175.4 (2) | C18—C17—C22—C21 | 0.0 (3) |
C9—C10—C12—C13 | 4.7 (2) | C16—C17—C22—C21 | 177.3 (2) |
Cg1 and Cg2 are the centroids of the C2–C7 and C17–C22 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1C···Cg1i | 0.98 | 2.84 | 3.728 (3) | 152 |
C4—H4···Cg2ii | 0.95 | 2.75 | 3.574 (2) | 146 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1/2, −y+1/2, z−1/2. |
Compound | Escherchia coli | Salmonella typhi | Staphylococcus aureus | Bacillus subtilis |
MBMCP | 07 | 12 | 27 | 14 |
Penecillin | 18 | 25 | 40 | 17 |
DMSO | – | – | – | – |
(-) No antibacterial activity |
Funding information
The authors acknowledge the Ministère de l'Enseignement Supérieur et de la Recherche Scientifique of Algeria for financial support.
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