research communications
Synthesis, E)-(2-phenylhydrazinylidene)methyl]quinoline
and Hirshfeld surface analysis of 2-chloro-3-[(aLaboratory of Organic and Analytical Chemistry, University Sultan Moulay Slimane, Faculty of Science and Technology, PO Box 523, Beni-Mellal, Morocco, and bLaboratoire de Chimie Appliquée des Matériaux, Centre Sciences des Matériaux, Faculty of Sciences, Mohammed V University in Rabat, Avenue Ibn Batouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: s.akhramez@gmail.com
A new quinoline-based hydrazone, C16H12ClN3, was synthesized by a condensation reaction of 2-chloro-3-formylquinoline with phenylhydrazine. The quinoline ring system is essentially planar (r.m.s. deviation = 0.012 Å), and forms a dihedral angle of 8.46 (10)° with the phenyl ring. The molecule adopts an E configuration with respect to the central C=N bond. In the crystal, molecules are linked by a C—H⋯π-phenyl interaction, forming zigzag chains propagating along the [10] direction. The N—H hydrogen atom does not participate in hydrogen bonding but is directed towards the phenyl ring of an adjacent molecule, so linking the chains via weak N—H⋯π interactions to form of a three-dimensional structure. The Hirshfeld surface analysis of the indicates that the most important contributions to the crystal packing are from H⋯H (35.5%), C⋯H/H⋯C (33.7%), Cl⋯H/H⋯Cl (12.3%), N⋯H/H⋯N (9.5%) contacts.
Keywords: crystal structure; quinoline hydrazine; phenyl hydrazine; C—H⋯π interaction; weak N—H⋯π interaction; Hirshfeld surface analysis.
CCDC reference: 1918954
1. Chemical context
Quinoline et al., 2018; Mandewale et al., 2017). Hydrazono-quinoline derivatives have been incorporated in many synthetic in order to enhance the cytotoxic activity (Bingul et al., 2016). Some of these derivatives may have anti-tuberculosis activity in vitro against various strains of Mycobacterium (Eswaran et al., 2010a,b, 2009). Others have been studied as antibacterial agents (Desai et al., 2014; Vlahov et al., 1990) and antimalarials (Vandekerckhove & D'hooghe, 2015; Lyon et al., 1999; Nayak et al., 2016; Hamama et al., 2018; Chavan et al., 2016).
are important classes of organic compounds that have long attracted attention because of their potential biological and pharmacological properties. They were conventionally prepared by a condensation reaction of the with A number of compounds incorporating the quinolinic heterocycle and a hydrazone have been synthesized and tested for their potential as antitumor agents (ErgucIn an attempt to find novel bioactive cytotoxic molecules, we have synthesized a series of quinoline-3-carbonitrile and 2-chloroquinoline derivatives by the . A similar synthesis has been reported in the literature (Korcz et al., 2018).
illustrated in Fig. 1The structure of the title compound 5, has been elucidated using 1H and 13C NMR spectroscopy and X-ray diffraction analysis.
2. Structural commentary
Compound 5 was prepared by a condensation reaction of 2-chloro-3-formylquinoline with phenylhydrazine. It crystallizes in the monoclinic Cc. It is composed of a phenyl ring and a quinoline ring system linked by a –CH=N—NH– spacer (Fig. 2), and adopts an E configuration relative to the hydrazonic N2=C10 bond [1.277 (3) Å].
The quinoline moiety is very slightly twisted, as indicated by the dihedral angle of 0.99 (10)° between the C1–C6 and N1/C1–C4/C9 rings. The phenyl ring (C11–C16) makes a dihedral angle of 8.49 (9)° with the mean plane of the quinoline ring system. The C1—Cl1 bond length of 1.750 (2) Å is in good agreement with the value of 1.756 (2) Å reported for a related structure, viz. (E)-1-[(2-chloroquinolin-3-yl)methylene]-2-(4-methylphenyl)hydrazine, also known as 2-chloro-3-{[(4-methylphenyl)hydrazono]methyl)quinoline} (Kumara et al., 2016).
3. Supramolecular features
In the crystal of compound 5, molecules are linked by a C—H⋯π-phenyl interaction (Table 1), with an H⋯centroid distance of 2.97 Å, forming zigzag chains propagating along the [10] direction, as shown in Fig. 3. The NH group of the hydrazone moiety does not form a hydrogen bond, but is directed towards the phenyl ring of an adjacent molecule, so linking the chains via a weak N—H⋯π interaction (Table 1), to form of a supramolecular three-dimensional structure (Fig. 4). There are no other significant intermolecular contacts shorter than those of the sum of the van der Waals radii of the individual atoms (PLATON; Spek, 2009).
4. Hirshfeld surface analysis and two-dimensional fingerprint plots
In order to visualize the role of weak intermolecular contacts in the crystal of compound 5, a Hirshfeld surface (HS) analysis (Spackman & Jayatilaka, 2009) was carried out and the associated two-dimensional fingerprint plots (McKinnon et al., 2007) generated using CrystalExplorer17.5 (Turner et al., 2017). The three-dimensional dnorm surface of 5 is shown in Fig. 5 with a standard surface resolution and a fixed colour scale of −0.1805 to 1.0413 a.u. The darkest red spots on the Hirshfeld surface indicate contact points with atoms participating in intermolecular C—H⋯π and N—H⋯π interactions that involve C7—H7 and N3—H3N and the phenyl substituent (Table 1).
As illustrated in Fig. 6, the corresponding fingerprint plots for compound 5 have characteristic pseudo-symmetric wings along the de and di diagonal axes. The presence of C—H⋯π and N—H⋯π interactions in the crystal are indicated by the pair of characteristic wings in the fingerprint plot delineated into C⋯H/H⋯C (Fig. 6c) and N⋯H/H⋯N (Fig. 6e) contacts (33.7 and 9.5% contributions, respectively, to the Hirshfeld surface). As shown in Fig. 6b, the most widely scattered points in the fingerprint plot are related to H⋯H contacts, which make a contribution of 35.5% to the Hirshfeld surface. There are also Cl⋯H/H⋯Cl (12.3%; Fig. 6d) and N⋯H/H⋯N (9.5%; Fig. 6e) contacts, with smaller contributions from C⋯C (3.5%), Cl⋯N (2.3%), C⋯N (2.2%) and C⋯Cl (1.1%) contacts.
5. Database survey
A search of the Cambridge Structural Database (CSD, version 5.40, update February 2019; Groom et al., 2016) using the hydrazinylidenemethyl quinoline system (Fig. 7) as the main skeleton revealed the presence of three similar structures to the title compound. One compound, (E)-2-chloro-3-{[2-(p-tolyl)hydrazineylidene]methyl}quinoline (5a) (CSD refcode ATIBOW; Kumara et al., 2016) has the C=N—N linkage with quinoline at position-3, as in the title compound 5. Two compounds have the C=N—N linkage with quinoline at position-2, viz. (E)-2-[(2-phenylhydrazineylidene)methyl]quinoline (5b) (WASJOS; Mukherjee et al., 2014) and (E)-2-{[2-(4-chlorophenyl)hydrazineylidene]methyl}quinoline (5c) (Chaur Valencia et al., 2018), as shown in Fig. 7. Table 2 presents a comparison between the principal bond lengths and angles of compound 5 and the related structures. The bond lengths in the hydrazonic linkage –C=N—N– remain almost unaltered in all four compounds, as do the C—C=N—N torsion angles.
6. Synthesis and crystallization
The multi-step reactions leading to the synthesis of the title compound 5 are illustrated in Fig. 1. Details of the syntheses of compounds 2, 3 and 5 are given below.
2-Chloroquinoline-3-carbaldehyde (3) was synthesized from acetylated aniline (2), according to a Vilsmeier–Haack reaction, either by conventional methods (Ramesh et al., 2008; Rajakumar & Raja, 2010), using microwaves (Mogilaiah et al., 2002) or ultrasonic irradiation (Ali et al., 2002).
In a first step, we tried a simple reaction of 2-chloroquinoline-3-carbaldehyde (3) and phenyl hydrazine in ethanol at room temperature or with heating to synthesize a new pyrazolo-quinoline derivative, 1-phenyl-1H-pyrazolo[3,4-b]quinoline (4). This was by a simple and different method from that described in the literature (Hamama et al., 2018). Unfortunately, the reaction did not take the desired route and led to the formation of the title compound 5, 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline, resulting from the attack of the nitrogen of hydrazine on the aldehyde at position 3 of quinoline.
The reaction conditions for the synthesis of compound 5 were optimized by changing the solvent, the catalyst and the temperature. The best yield of 92% was obtained by the conventional method, viz. refluxing in ethanol for 10 min and without a catalyst. In the 1H NMR spectra of this hydrazone quinoline, the single resonance for the proton of the –N(H)N=group is observed at δ = 12.01 ppm, whereas the corresponding amide N=CH proton appears as a broad singlet at 8.45 ppm. The spectra show that the chemical shifts of the protons on the aryl group have been assigned correctly. The structure of this hydrazono-quinoline, 5, was confirmed by the single-crystal X-ray diffraction study.
Synthesis of N-phenylacetamide (2):
To a 500 ml flask containing 250 ml of water and 25% hydrochloric acid (15 ml, 0.108 mol), aniline (9.75 ml, 0.108 mol) was added. The reaction mixture was heated at 323 K for 10 min. Then, and at room temperature, acetic anhydride (10.3 ml, 0.108 mol) and sodium acetate (16.4 g, 0.2 mol) were added. The mixture was stirred for 20 min. The product obtained was filtered off and then dried, giving a white solid (yield 86%, m.p. 384–386 K).
1H NMR (300 Hz, CDCl3): δ (ppm) 7.42 (1H, s, NH), 7.77–7.22 (5H, m, HAr), 2,21 (3H, s, CH3); 13C NMR (75 Hz, CDCl3): δ (ppm) 169.9 (CO), 140.0 (C), 129.6 (2C), 128.7 (C), 122.3 (2CH), 20.9 (CH3).
Synthesis of 2-chloroquinoline-3-carbaldehyde (3):
Phosphorus oxychloride (POCl3) (35 ml, 374 mmol) was added dropwise with magnetic stirring at 273 K, to anhydrous N,N-dimethylformamide (DMF) (10 ml, 135 mmol) in a double-necked flask. Once the addition was complete, the temperature was allowed to rise and the reaction mixture was left stirring for 30 min. Acetanilide 2 (7.29 g, 54 mmol) was then added and the reaction mixture was heated at 348 K for 4 h. Subsequently and at room temperature, the reaction mixture was poured in small portions into an Erlenmeyer flask containing a mixture of ice/water (200 ml) maintained with magnetic stirring. The precipitate formed was filtered and then washed with water (100 ml). Compound 3 was obtained as a yellow solid (yield 68%, m.p. 418–420 K).
1HNMR (300 Hz, CDCl3): δ (ppm) 10.59 (1H, s, CHO), 8.80 (1H, s), 8.07–7.66 (4H, m, HAr); 13CNMR (75 Hz, CDCl3): δ (ppm) 189.2 (CHO), 150.1 (C), 149.5 (C), 140.2 (CH), 133.6 (CH), 129.7 (C), 128.5 (CH), 128.1 (CH), 126.4 (CH), 126.3 (C).
Synthesis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline (5):
To a solution of 2-chloroquinoline-3-carbaldehyde (3) (191.0 mg, 1 mmol) in ethanol was added phenylhydrazine (0.99 ml, 1 mmol). The mixture was stirred and refluxed for 10 min. The precipitate that formed was filtered, then washed repeatedly with diethyl ether. Subsequently, the precipitate was dissolved in pure ethanol. Pale-brown block-like crystals were obtained by slow evaporation of this ethanolic solution at room temperature. The crystals were then dried under vacuum (yield 92%, m.p. 429–429 K).
1HNMR (300 Hz, CDCl3): 12.01 (s, 1H, NH), 8.97 (s, 1H, Hquinoline), 8.45 (s, 1H, N=CH), 7.90–8.00 (m, 4H, Ar-H), 7.62 (d, J = 8.3 Hz, 2H, Ar-H), 7.33 (d, J = 7.9 Hz, 2H, Ar-H), 7.06 (t, J = 7.9 Hz, 1H, Ar-H); 13CNMR (75 Hz, CDCl3): 121.8, 127.8 (three overlapping signals), 154.1 (CCl), 147.4 (C), 146.3 (C), 135.8 (CN), 133.4 (C), 131.8 (C), 129.9 (2C), 129.5(C), 128.8 (C), 128.0 (C), 127.7 (C), 126.6 (C), 124.1 (C), 122.7 (C), 116.6 (2C).
7. Refinement
Crystal data, data collection and structure . All H atoms could be located in a difference-Fourier map. During they were placed in calculated positions and treated as riding: N—H = 0.86 Å, C—H = 0.93 Å with Uiso(H) = 1.2Ueq(N,C).
details are summarized in Table 3
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Supporting information
CCDC reference: 1918954
https://doi.org/10.1107/S2056989019007692/su5497sup1.cif
contains datablocks I, Gobal. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019007692/su5497Isup2.hkl
Data collection: APEX3 (Bruker, 2016); cell
SAINT-Plus (Bruker, 2016); data reduction: SAINT-Plus (Bruker, 2016); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).C16H12ClN3 | F(000) = 584 |
Mr = 281.74 | Dx = 1.377 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2114 (4) Å | Cell parameters from 2981 reflections |
b = 19.4553 (11) Å | θ = 2.8–27.1° |
c = 11.2520 (7) Å | µ = 0.27 mm−1 |
β = 91.883 (2)° | T = 296 K |
V = 1359.01 (14) Å3 | Block, brown |
Z = 4 | 0.35 × 0.26 × 0.20 mm |
Bruker D8 VENTURE Super DUO diffractometer | 2981 independent reflections |
Radiation source: INCOATEC IµS micro-focus source | 2712 reflections with I > 2σ(I) |
HELIOS mirror optics monochromator | Rint = 0.029 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 27.1°, θmin = 2.8° |
φ and ω scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −24→24 |
Tmin = 0.678, Tmax = 0.746 | l = −14→14 |
21613 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.029 | w = 1/[σ2(Fo2) + (0.0402P)2 + 0.2303P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.072 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.15 e Å−3 |
2981 reflections | Δρmin = −0.14 e Å−3 |
182 parameters | Extinction correction: (SHELXL2014; Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0046 (13) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack x determined using 1200 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.023 (15) |
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 | ||
Cl1 | 0.50087 (11) | 0.42496 (3) | 0.50091 (7) | 0.0554 (2) | |
N1 | 0.1727 (3) | 0.34866 (11) | 0.44617 (16) | 0.0421 (4) | |
N2 | 0.6213 (3) | 0.40817 (9) | 0.12487 (17) | 0.0419 (4) | |
N3 | 0.8016 (3) | 0.43842 (10) | 0.08642 (18) | 0.0463 (5) | |
H3N | 0.8814 | 0.4624 | 0.1345 | 0.056* | |
C1 | 0.3350 (3) | 0.37935 (11) | 0.39999 (19) | 0.0393 (5) | |
C2 | 0.3882 (3) | 0.37981 (11) | 0.27845 (18) | 0.0371 (5) | |
C3 | 0.2499 (4) | 0.34346 (12) | 0.20400 (18) | 0.0395 (5) | |
H3 | 0.2744 | 0.3424 | 0.1229 | 0.047* | |
C4 | 0.0728 (4) | 0.30794 (11) | 0.24785 (18) | 0.0379 (5) | |
C5 | −0.0709 (4) | 0.26905 (12) | 0.1754 (2) | 0.0470 (5) | |
H5 | −0.0510 | 0.2665 | 0.0940 | 0.056* | |
C6 | −0.2389 (4) | 0.23516 (13) | 0.2241 (2) | 0.0511 (6) | |
H6 | −0.3328 | 0.2096 | 0.1756 | 0.061* | |
C7 | −0.2712 (5) | 0.23870 (13) | 0.3473 (3) | 0.0544 (6) | |
H7 | −0.3850 | 0.2149 | 0.3798 | 0.065* | |
C8 | −0.1374 (4) | 0.27659 (13) | 0.4190 (2) | 0.0498 (6) | |
H8 | −0.1619 | 0.2794 | 0.4999 | 0.060* | |
C9 | 0.0384 (4) | 0.31169 (11) | 0.37146 (19) | 0.0394 (5) | |
C10 | 0.5788 (4) | 0.41442 (11) | 0.2346 (2) | 0.0421 (5) | |
H10 | 0.6671 | 0.4404 | 0.2855 | 0.051* | |
C11 | 0.8577 (4) | 0.43052 (11) | −0.0315 (2) | 0.0405 (5) | |
C12 | 0.7277 (4) | 0.39628 (13) | −0.1134 (2) | 0.0487 (5) | |
H12 | 0.5980 | 0.3773 | −0.0905 | 0.058* | |
C13 | 0.7903 (5) | 0.39014 (15) | −0.2298 (2) | 0.0574 (7) | |
H13 | 0.7017 | 0.3670 | −0.2847 | 0.069* | |
C14 | 0.9814 (5) | 0.41769 (13) | −0.2655 (2) | 0.0582 (7) | |
H14 | 1.0218 | 0.4137 | −0.3441 | 0.070* | |
C15 | 1.1114 (5) | 0.45108 (15) | −0.1835 (3) | 0.0620 (7) | |
H15 | 1.2414 | 0.4697 | −0.2067 | 0.074* | |
C16 | 1.0518 (5) | 0.45757 (15) | −0.0663 (2) | 0.0563 (7) | |
H16 | 1.1420 | 0.4800 | −0.0113 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0558 (3) | 0.0700 (4) | 0.0398 (3) | −0.0078 (3) | −0.0075 (2) | −0.0099 (3) |
N1 | 0.0487 (10) | 0.0489 (10) | 0.0288 (8) | −0.0018 (8) | 0.0014 (8) | −0.0004 (7) |
N2 | 0.0435 (11) | 0.0417 (10) | 0.0407 (10) | −0.0026 (8) | 0.0042 (8) | 0.0034 (8) |
N3 | 0.0471 (11) | 0.0510 (11) | 0.0411 (10) | −0.0138 (9) | 0.0049 (8) | −0.0024 (8) |
C1 | 0.0438 (12) | 0.0401 (11) | 0.0336 (10) | 0.0036 (9) | −0.0052 (9) | −0.0029 (9) |
C2 | 0.0416 (12) | 0.0352 (11) | 0.0345 (11) | 0.0044 (9) | 0.0015 (9) | 0.0009 (8) |
C3 | 0.0474 (12) | 0.0425 (12) | 0.0290 (10) | 0.0001 (9) | 0.0052 (9) | −0.0021 (8) |
C4 | 0.0453 (12) | 0.0349 (10) | 0.0335 (10) | 0.0029 (9) | 0.0025 (9) | 0.0002 (8) |
C5 | 0.0574 (14) | 0.0469 (12) | 0.0368 (12) | −0.0040 (11) | 0.0024 (10) | −0.0047 (10) |
C6 | 0.0566 (14) | 0.0465 (14) | 0.0499 (15) | −0.0112 (11) | −0.0021 (12) | −0.0065 (10) |
C7 | 0.0541 (15) | 0.0536 (14) | 0.0561 (15) | −0.0123 (12) | 0.0110 (12) | 0.0013 (12) |
C8 | 0.0575 (15) | 0.0561 (15) | 0.0361 (12) | −0.0054 (12) | 0.0092 (10) | 0.0025 (11) |
C9 | 0.0459 (12) | 0.0379 (11) | 0.0343 (10) | 0.0020 (9) | 0.0016 (9) | 0.0016 (8) |
C10 | 0.0452 (12) | 0.0426 (11) | 0.0385 (11) | −0.0024 (10) | 0.0011 (9) | −0.0009 (9) |
C11 | 0.0454 (12) | 0.0364 (12) | 0.0401 (12) | −0.0003 (9) | 0.0050 (9) | 0.0038 (8) |
C12 | 0.0464 (13) | 0.0539 (13) | 0.0457 (13) | −0.0040 (11) | −0.0004 (10) | 0.0031 (10) |
C13 | 0.0755 (19) | 0.0575 (16) | 0.0388 (13) | 0.0056 (14) | −0.0042 (12) | 0.0008 (11) |
C14 | 0.084 (2) | 0.0474 (14) | 0.0441 (13) | 0.0173 (14) | 0.0182 (13) | 0.0101 (11) |
C15 | 0.0650 (18) | 0.0549 (15) | 0.0677 (18) | −0.0024 (13) | 0.0277 (15) | 0.0071 (13) |
C16 | 0.0563 (15) | 0.0560 (15) | 0.0572 (16) | −0.0156 (12) | 0.0113 (12) | −0.0022 (12) |
Cl1—C1 | 1.750 (2) | C6—H6 | 0.9300 |
N1—C1 | 1.295 (3) | C7—C8 | 1.356 (4) |
N1—C9 | 1.369 (3) | C7—H7 | 0.9300 |
N2—C10 | 1.277 (3) | C8—C9 | 1.408 (3) |
N2—N3 | 1.349 (3) | C8—H8 | 0.9300 |
N3—C11 | 1.391 (3) | C10—H10 | 0.9300 |
N3—H3N | 0.8600 | C11—C12 | 1.377 (3) |
C1—C2 | 1.417 (3) | C11—C16 | 1.384 (3) |
C2—C3 | 1.376 (3) | C12—C13 | 1.384 (3) |
C2—C10 | 1.461 (3) | C12—H12 | 0.9300 |
C3—C4 | 1.402 (3) | C13—C14 | 1.374 (4) |
C3—H3 | 0.9300 | C13—H13 | 0.9300 |
C4—C5 | 1.409 (3) | C14—C15 | 1.370 (5) |
C4—C9 | 1.416 (3) | C14—H14 | 0.9300 |
C5—C6 | 1.365 (4) | C15—C16 | 1.387 (4) |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
C6—C7 | 1.409 (4) | C16—H16 | 0.9300 |
C1—N1—C9 | 117.55 (18) | C7—C8—H8 | 119.8 |
C10—N2—N3 | 117.97 (19) | C9—C8—H8 | 119.8 |
N2—N3—C11 | 119.62 (19) | N1—C9—C8 | 119.1 (2) |
N2—N3—H3N | 120.2 | N1—C9—C4 | 121.43 (19) |
C11—N3—H3N | 120.2 | C8—C9—C4 | 119.5 (2) |
N1—C1—C2 | 126.8 (2) | N2—C10—C2 | 118.6 (2) |
N1—C1—Cl1 | 115.01 (16) | N2—C10—H10 | 120.7 |
C2—C1—Cl1 | 118.15 (17) | C2—C10—H10 | 120.7 |
C3—C2—C1 | 115.04 (19) | C12—C11—C16 | 119.4 (2) |
C3—C2—C10 | 121.86 (19) | C12—C11—N3 | 122.1 (2) |
C1—C2—C10 | 123.08 (19) | C16—C11—N3 | 118.4 (2) |
C2—C3—C4 | 121.36 (19) | C11—C12—C13 | 119.9 (2) |
C2—C3—H3 | 119.3 | C11—C12—H12 | 120.0 |
C4—C3—H3 | 119.3 | C13—C12—H12 | 120.0 |
C3—C4—C5 | 123.4 (2) | C14—C13—C12 | 121.0 (3) |
C3—C4—C9 | 117.76 (19) | C14—C13—H13 | 119.5 |
C5—C4—C9 | 118.9 (2) | C12—C13—H13 | 119.5 |
C6—C5—C4 | 120.4 (2) | C15—C14—C13 | 118.9 (2) |
C6—C5—H5 | 119.8 | C15—C14—H14 | 120.5 |
C4—C5—H5 | 119.8 | C13—C14—H14 | 120.5 |
C5—C6—C7 | 120.4 (2) | C14—C15—C16 | 120.9 (3) |
C5—C6—H6 | 119.8 | C14—C15—H15 | 119.5 |
C7—C6—H6 | 119.8 | C16—C15—H15 | 119.5 |
C8—C7—C6 | 120.5 (2) | C11—C16—C15 | 119.8 (3) |
C8—C7—H7 | 119.8 | C11—C16—H16 | 120.1 |
C6—C7—H7 | 119.8 | C15—C16—H16 | 120.1 |
C7—C8—C9 | 120.4 (2) |
Cg is the centroid of the C11–C16 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···Cgi | 0.93 | 2.97 | 3.700 (3) | 136 |
N3—H3N···Cgii | 0.86 | 3.30 | 4.060 | 149 |
Symmetry codes: (i) x−3/2, −y+1/2, z+1/2; (ii) x, −y+1, z+1/2. |
Compound | C2—C10 | C10═N2 | N2—N3 | N3—C11 | C—C═N—N |
5 | 1.461 (3) | 1.277 (3) | 1.349 (3) | 1.391 (3) | -177.79 (19) |
5a | 1.468 | 1.282 | 1.354 | 1.400 | -178.40 |
5b | 1.452 | 1.289 | 1.350 | 1.393 | -179.10 |
5c | 1.456 | 1.279 | 1.348 | 1.389 | 179.10 |
Notes: 5 this study; 5a Kumara et al. (2016); 5b Mukherjee et al. (2014); 5c Chaur Valencia et al. (2018). |
Acknowledgements
The authors thank Faculty of Science, Mohammed V University in Rabat, Morocco, for the X-ray measurements.
References
Ali, M. M., Sana, S., Tasneem, R. K. C., Rajanna, K. C. & Saiprakash, P. K. (2002). Synth. Commun. 32, 1351–1356. Web of Science CrossRef CAS Google Scholar
Bingul, M., Tan, O., Gardner, C. R., Sutton, S. K., Arndt, G. M., Marshall, G. M., Cheung, B. B., Kumar, N. & Black, D. St C. (2016). Molecules, 21, 916–934. Web of Science CSD CrossRef Google Scholar
Bruker (2016). APEX3, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chaur Valencia, M. N., Romero, E. L., Gutiérrez, G., Soto Monsalve, M., D'Vries, R. & Zuluaga, H. F. (2018). Rev. Colomb. Quim. 47(2), 63–72. Web of Science CrossRef Google Scholar
Chavan, H. V., Sirsat, D. M. & Mule, Y. B. (2016). Iran. Chem. Commun, 4, 373–388. Google Scholar
Desai, N. C., Kotadiya, G. M. & Trivedi, A. R. (2014). Bioorg. Med. Chem. Lett. 24, 3126–3130. Web of Science CrossRef CAS PubMed Google Scholar
Erguc, A., Altinop, M. D., Atli, O., Sever, B., Iscan, G., Gormus, G. & Ozdemir, A. (2018). Lett. Drug. Des. Discov. 15, 193–202. CAS Google Scholar
Eswaran, S., Adhikari, A. V., Chowdhury, I. H., Pal, N. K. & Thomas, K. D. (2010a). Eur. J. Med. Chem. 45, 3374–3383. Web of Science CrossRef CAS PubMed Google Scholar
Eswaran, S., Adhikari, A. V., Pal, N. K. & Chowdhury, I. H. (2010b). Bioorg. Med. Chem. Lett. 20, 1040–1044. Web of Science CrossRef CAS PubMed Google Scholar
Eswaran, S., Adhikari, A. V. & Shetty, N. S. (2009). Eur. J. Med. Chem. 44, 4637–4647. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS 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
Hamama, W. S., Ibrahim, M. E., Gooda, A. A. & Zoorob, H. H. (2018). RSC Adv. 8, 8484–8515. Web of Science CrossRef CAS Google Scholar
Korcz, M., Sączewski, F., Bednarski, P. J. & Kornicka, A. (2018). Molecules, 23, 1497–1518. Web of Science CrossRef Google Scholar
Kumara, T. H. S., Nagendrappa, G., Chandrika, N., Sowmya, H. B. V., Kaur, M., Jasinski, J. P. & Glidewell, C. (2016). Acta Cryst. C72, 670–678. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lyon, M. A., Lawrence, S., Williams, D. J. & Jackson, Y. A. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 437–442. Web of Science CSD CrossRef Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mandewale, M. C., Patil, U. C., Shedge, S. V. & Dappadwad, U. R. (2017). J. Basic Appl. Sci, 6, 354–361. Google Scholar
McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. Web of Science CrossRef Google Scholar
Mogilaiah, K., Reddy, N. V. & Rao, R. B. (2002). Indian J. Heterocycl. Chem. 11, 253–261. CAS Google Scholar
Mukherjee, S., Paul, A. K., Krishna Rajak, K. & Stoeckli-Evans, H. (2014). Sens. Actuators B Chem. 203, 150–156. Web of Science CSD CrossRef CAS Google Scholar
Nayak, G., Shrivastava, B. & Singhai, A. K. (2016). Int. J. Curr. Pharm. Res, 8, 64–67. CAS Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Rajakumar, P. & Raja, R. (2010). Tetrahedron Lett. 51, 4365–4370. Web of Science CrossRef CAS Google Scholar
Ramesh, E., Sree Vidhya, T. K. & Raghunathan, R. (2008). Tetrahedron Lett. 49, 2810–2814. Web of Science CrossRef CAS 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
Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19–32. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17.5. The University of Western Australia. Google Scholar
Vandekerckhove, S. & D'hooghe, M. (2015). Bioorg. Med. Chem. 23, 5098–5119. Web of Science CrossRef CAS PubMed Google Scholar
Vlahov, R., Parushev, S., Vlahov, J., Nickel, P. & Snatzke, G. (1990). Pure Appl. Chem. 62, 1303–1306. CrossRef Web of Science Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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