organic compounds
2-p-Tolyl-2,3-dihydroquinolin-4(1H)-one
aLaboratoire des Produits Naturels d'Origine Végétale, et de Synthèse Organique, PHYSYNOR Université Constantine 1, 25000 Constantine, Algeria, bUnité de Recherche de Cimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, 25000 , Algeria, and cDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi, 04000 Oum El Bouaghi, Algeria
*Correspondence e-mail: bouacida_sofiane@yahoo.fr
In the title molecule, C16H15NO, the tetrahydropyridine ring is in a sofa conformation with the methine C atom forming the flap. The dihedral angle between the benzene rings is 80.85 (8)°. In the crystal, molecules are arranged in alternating double layers parallel to (100) and are connected along [001] by N—H⋯O hydrogen bonds. In addition, weak C—H⋯π interactions are observed.
CCDC reference: 982977
Related literature
For applications of quinolines, see: Hepworth (1984). For the synthesis and applications of similar compounds see: Donnelly & Farrell (1990a,b); Chandrasekhar et al. (2007); Kumar et al. (2004); Gordon (2001); Olivier-Bourbigou & Magna (2002); Tokes & Szilagyi (1987); Tokes & Litkei (1993); Benzerka et al. (2012, 2013); Hayour et al. (2011) Chelghoum et al. (2012). For related structures, see: Tokes et al. (1992); Benzerka et al. (2011); Bouraiou et al. (2011).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2006); cell SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program).
Supporting information
CCDC reference: 982977
10.1107/S1600536814001676/lh5684sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001676/lh5684Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001676/lh5684Isup3.cml
The substituted 2'-aminochalcone (0.5 mmol) and [bmim]BF4 (1 g) were heated at 423K for 2.5 h. Under these conditions, the title compound was successfully synthesized in good yield (92%). Single crystals suitable for the X-ray
were obtained by dissolving the pure compound in an Et2O/CHCl3 mixture and allowing the solution to slowly evaporate at room temperature.All non-H atoms were refined with anisotropic atomic displacement parameters. Approximate positions for all the H atoms were first obtained from the difference
However, the H atoms were situated in idealized positions and the H-atoms were refined in a riding-motion approximation. The applied constraints were as follow: Caryl—Haryl = 0.95 Å; Cmethylene—Hmethylene = 0.99 Å; Cmethyl—Hmethyl = 0.98 Å; and Cmethine—Hmethine = 1.0 Å; The idealized methyl group was allowed to rotate about the C—C bond during the by application of the command AFIX 137 in SHELXL97 (Sheldrick, 2008). Uiso(Hmethyl) = 1.5Ueq(Cmethyl) or Uiso(Haryl, methylene, methine) = 1.2 Ueq(Caryl, methylene and methine). Atom H1N was found in a difference and refined isotropically with Uiso(H) = 1.2Ueq(N)The role of π interactions are observed.
has become increasingly important in designing new classes of structural entities of medicinal importance. Quinolines are interesting synthetic targets because they act as building blocks for a large number of natural products (Hepworth, 1984). The formation of 2,3-dihydroquinolin-4(1H)-ones is generally accomplished by acid- or base-catalyzed isomerization of substituted 2'-aminochalcones (Donnelly & Farrell, 1990a,b; Tokes & Litkei, 1993). Most of these procedures involve the use of corrosive reagents such as orthophosphoric acid, acetic acid, or strong alkali. Many attempts have therefore been made to explore efficient catalysts to accelerate this reaction. Some of them are of limited synthetic scope due to low yields, long reaction times, and the need for a large amount of catalyst, specialized solvents (Tokes & Szilagyi, 1987; Tokes et al., 1992), or microwave activation (Kumar et al., 2004; Gordon, 2001; Olivier-Bourbigou & Magna, 2002). As part of our continuingeffort toward the development of new methods for the synthesis of biologically relevant (Benzerka et al., 2012, 2013; Hayour et al., 2011), we have, recently, developed a procedure using butylmethylimidazolium(bmim).BF4 as a green solvent to provide an efficient and convenient protocol for the synthesis of 2,3-dihydroquinolin-4(1H)-ones from 2'-aminochalcones without the requirement for an additional catalyst (Chelghoum et al., 2012). We wish to describe herein the synthesis and single-crystal X-ray structure of 2-p-tolyl-2,3-dihydroquinolin-4(1H)-one (I). The molecular structure and the atom-numbering scheme of (I) are shown in Fig. 1. The molecule of consists of a dihydroquinolin-4(1H)-one moiety attached to tolyl group. The (1H)-dihydropyridine ring (C2/C10/C11/C13/C18/N1) is in a sofa conformation with atom C2 forming the flap. The dihedral angle between the two benzene rings (C3-C9/C13-C18) is 80.85 (8)°. The crystal packing can be described as alternating double layers parallel to (100) (Fig. 2). Intermolecular N—H···O hydrogen bonds (Fig.3; Table. 1) link the molecules along [100]. In addition, weak C—H···For applications of quinolines, see: Hepworth (1984). For the synthesis and applications of similar compounds see: Donnelly & Farrell (1990a,b); Chandrasekhar et al. (2007); Kumar et al. (2004); Gordon (2001); Olivier-Bourbigou & Magna (2002); Tokes & Szilagyi (1987); Tokes & Litkei (1993); Benzerka et al. (2012, 2013); Hayour et al. (2011) Chelghoum et al. (2012). For related structures, see: Tokes et al. (1992); Benzerka et al. (2011); Bouraiou et al. (2011).
Data collection: APEX2 (Bruker, 2006); cell
SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program).Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radius. | |
Fig. 2. The crystal packing showing alternating double layers parallel to (100) viewed along the c axis. | |
Fig. 3. Part of the crystal structure viewed along the b axis showing hydrogen bond as dashed lines. |
C16H15NO | F(000) = 1008 |
Mr = 237.29 | Dx = 1.248 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2437 reflections |
a = 17.6363 (14) Å | θ = 2.4–27.5° |
b = 10.7968 (9) Å | µ = 0.08 mm−1 |
c = 13.6308 (9) Å | T = 150 K |
β = 103.260 (3)° | Prism, colourless |
V = 2526.3 (3) Å3 | 0.52 × 0.33 × 0.27 mm |
Z = 8 |
Bruker APEXII diffractometer | 2279 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
CCD rotation images, thin slices scans | θmax = 27.5°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −22→22 |
Tmin = 0.873, Tmax = 0.979 | k = −14→10 |
6746 measured reflections | l = −17→10 |
2875 independent reflections |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.153 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0758P)2 + 2.2919P] where P = (Fo2 + 2Fc2)/3 |
2875 reflections | (Δ/σ)max = 0.001 |
167 parameters | Δρmax = 0.69 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C16H15NO | V = 2526.3 (3) Å3 |
Mr = 237.29 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 17.6363 (14) Å | µ = 0.08 mm−1 |
b = 10.7968 (9) Å | T = 150 K |
c = 13.6308 (9) Å | 0.52 × 0.33 × 0.27 mm |
β = 103.260 (3)° |
Bruker APEXII diffractometer | 2875 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 2279 reflections with I > 2σ(I) |
Tmin = 0.873, Tmax = 0.979 | Rint = 0.026 |
6746 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.153 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.69 e Å−3 |
2875 reflections | Δρmin = −0.28 e Å−3 |
167 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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 | ||
C2 | 0.58114 (9) | 0.12806 (16) | 0.08077 (12) | 0.0263 (4) | |
H2 | 0.5264 | 0.0972 | 0.0596 | 0.032* | |
C3 | 0.58821 (10) | 0.24612 (15) | 0.02362 (12) | 0.0260 (4) | |
C4 | 0.52341 (10) | 0.29679 (18) | −0.03934 (14) | 0.0346 (4) | |
H4 | 0.4744 | 0.2568 | −0.0469 | 0.042* | |
C5 | 0.52839 (11) | 0.40454 (19) | −0.09163 (15) | 0.0378 (4) | |
H5 | 0.4824 | 0.438 | −0.1337 | 0.045* | |
C6 | 0.59864 (10) | 0.46561 (16) | −0.08463 (12) | 0.0273 (4) | |
C7 | 0.60403 (12) | 0.58261 (18) | −0.14265 (15) | 0.0402 (5) | |
H7A | 0.6587 | 0.608 | −0.1317 | 0.06* | |
H7B | 0.574 | 0.6483 | −0.1194 | 0.06* | |
H7C | 0.5829 | 0.5677 | −0.2147 | 0.06* | |
C8 | 0.66448 (9) | 0.41410 (17) | −0.02209 (12) | 0.0281 (4) | |
H8 | 0.7136 | 0.4532 | −0.0161 | 0.034* | |
C9 | 0.65959 (10) | 0.30599 (17) | 0.03197 (12) | 0.0295 (4) | |
H9 | 0.7052 | 0.2727 | 0.0749 | 0.035* | |
C10 | 0.60048 (10) | 0.14901 (16) | 0.19407 (11) | 0.0284 (4) | |
H10A | 0.6503 | 0.1948 | 0.2132 | 0.034* | |
H10B | 0.5595 | 0.2018 | 0.2113 | 0.034* | |
C11 | 0.60719 (10) | 0.03170 (16) | 0.25526 (12) | 0.0269 (4) | |
C13 | 0.63292 (9) | −0.07957 (16) | 0.21014 (11) | 0.0233 (3) | |
C14 | 0.64681 (10) | −0.19096 (17) | 0.26412 (12) | 0.0296 (4) | |
H14 | 0.6365 | −0.1956 | 0.3294 | 0.035* | |
C15 | 0.67503 (10) | −0.29353 (17) | 0.22452 (13) | 0.0312 (4) | |
H15 | 0.6843 | −0.3684 | 0.262 | 0.037* | |
C16 | 0.68997 (9) | −0.28610 (16) | 0.12829 (13) | 0.0287 (4) | |
H16 | 0.7099 | −0.3564 | 0.1007 | 0.034* | |
C17 | 0.67624 (9) | −0.17860 (16) | 0.07284 (12) | 0.0253 (4) | |
H17 | 0.6868 | −0.1755 | 0.0076 | 0.03* | |
C18 | 0.64660 (8) | −0.07303 (15) | 0.11196 (11) | 0.0206 (3) | |
N1 | 0.63337 (8) | 0.03393 (13) | 0.05626 (10) | 0.0229 (3) | |
H1N | 0.6284 (11) | 0.0219 (18) | −0.0085 (16) | 0.028* | |
O12 | 0.59607 (9) | 0.03372 (13) | 0.34096 (9) | 0.0416 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.0283 (8) | 0.0280 (9) | 0.0236 (8) | −0.0016 (7) | 0.0076 (6) | −0.0007 (6) |
C3 | 0.0363 (9) | 0.0234 (8) | 0.0213 (7) | 0.0002 (7) | 0.0130 (6) | −0.0022 (6) |
C4 | 0.0292 (8) | 0.0348 (10) | 0.0393 (10) | −0.0087 (7) | 0.0068 (7) | 0.0020 (8) |
C5 | 0.0291 (9) | 0.0382 (11) | 0.0413 (10) | −0.0014 (8) | −0.0018 (7) | 0.0088 (8) |
C6 | 0.0341 (9) | 0.0227 (8) | 0.0257 (8) | −0.0020 (7) | 0.0080 (6) | −0.0003 (6) |
C7 | 0.0520 (11) | 0.0280 (10) | 0.0395 (10) | −0.0034 (8) | 0.0084 (8) | 0.0063 (8) |
C8 | 0.0237 (7) | 0.0313 (9) | 0.0301 (8) | −0.0046 (7) | 0.0075 (6) | −0.0040 (7) |
C9 | 0.0291 (8) | 0.0331 (10) | 0.0252 (8) | 0.0069 (7) | 0.0042 (6) | 0.0009 (7) |
C10 | 0.0406 (9) | 0.0267 (9) | 0.0198 (7) | 0.0029 (7) | 0.0110 (7) | −0.0022 (6) |
C11 | 0.0333 (8) | 0.0314 (9) | 0.0166 (7) | 0.0006 (7) | 0.0072 (6) | −0.0006 (6) |
C13 | 0.0255 (7) | 0.0265 (8) | 0.0179 (7) | −0.0004 (6) | 0.0054 (6) | −0.0005 (6) |
C14 | 0.0353 (9) | 0.0329 (10) | 0.0210 (7) | 0.0009 (7) | 0.0074 (6) | 0.0050 (7) |
C15 | 0.0338 (9) | 0.0278 (9) | 0.0315 (9) | 0.0023 (7) | 0.0063 (7) | 0.0063 (7) |
C16 | 0.0277 (8) | 0.0260 (9) | 0.0339 (9) | 0.0014 (7) | 0.0098 (7) | −0.0027 (7) |
C17 | 0.0265 (8) | 0.0277 (9) | 0.0238 (7) | −0.0021 (6) | 0.0100 (6) | −0.0035 (6) |
C18 | 0.0197 (7) | 0.0236 (8) | 0.0187 (7) | −0.0041 (6) | 0.0047 (5) | −0.0022 (6) |
N1 | 0.0313 (7) | 0.0236 (7) | 0.0159 (6) | −0.0003 (5) | 0.0097 (5) | −0.0013 (5) |
O12 | 0.0695 (10) | 0.0406 (8) | 0.0189 (6) | 0.0102 (7) | 0.0186 (6) | 0.0020 (5) |
C2—N1 | 1.461 (2) | C10—C11 | 1.506 (2) |
C2—C3 | 1.514 (2) | C10—H10A | 0.99 |
C2—C10 | 1.520 (2) | C10—H10B | 0.99 |
C2—H2 | 1 | C11—O12 | 1.228 (2) |
C3—C4 | 1.376 (2) | C11—C13 | 1.468 (2) |
C3—C9 | 1.396 (2) | C13—C14 | 1.402 (2) |
C4—C5 | 1.378 (3) | C13—C18 | 1.415 (2) |
C4—H4 | 0.95 | C14—C15 | 1.374 (3) |
C5—C6 | 1.387 (2) | C14—H14 | 0.95 |
C5—H5 | 0.95 | C15—C16 | 1.398 (2) |
C6—C8 | 1.389 (2) | C15—H15 | 0.95 |
C6—C7 | 1.505 (2) | C16—C17 | 1.376 (2) |
C7—H7A | 0.98 | C16—H16 | 0.95 |
C7—H7B | 0.98 | C17—C18 | 1.409 (2) |
C7—H7C | 0.98 | C17—H17 | 0.95 |
C8—C9 | 1.394 (2) | C18—N1 | 1.372 (2) |
C8—H8 | 0.95 | N1—H1N | 0.88 (2) |
C9—H9 | 0.95 | ||
N1—C2—C3 | 109.72 (13) | C11—C10—C2 | 114.09 (14) |
N1—C2—C10 | 109.24 (13) | C11—C10—H10A | 108.7 |
C3—C2—C10 | 111.82 (14) | C2—C10—H10A | 108.7 |
N1—C2—H2 | 108.7 | C11—C10—H10B | 108.7 |
C3—C2—H2 | 108.7 | C2—C10—H10B | 108.7 |
C10—C2—H2 | 108.7 | H10A—C10—H10B | 107.6 |
C4—C3—C9 | 118.11 (15) | O12—C11—C13 | 123.04 (15) |
C4—C3—C2 | 120.08 (15) | O12—C11—C10 | 120.15 (15) |
C9—C3—C2 | 121.81 (15) | C13—C11—C10 | 116.66 (13) |
C3—C4—C5 | 121.08 (16) | C14—C13—C18 | 119.47 (15) |
C3—C4—H4 | 119.5 | C14—C13—C11 | 121.05 (14) |
C5—C4—H4 | 119.5 | C18—C13—C11 | 119.45 (14) |
C4—C5—C6 | 121.84 (16) | C15—C14—C13 | 121.38 (15) |
C4—C5—H5 | 119.1 | C15—C14—H14 | 119.3 |
C6—C5—H5 | 119.1 | C13—C14—H14 | 119.3 |
C5—C6—C8 | 117.36 (16) | C14—C15—C16 | 119.03 (16) |
C5—C6—C7 | 121.72 (16) | C14—C15—H15 | 120.5 |
C8—C6—C7 | 120.92 (16) | C16—C15—H15 | 120.5 |
C6—C7—H7A | 109.5 | C17—C16—C15 | 121.09 (16) |
C6—C7—H7B | 109.5 | C17—C16—H16 | 119.5 |
H7A—C7—H7B | 109.5 | C15—C16—H16 | 119.5 |
C6—C7—H7C | 109.5 | C16—C17—C18 | 120.56 (14) |
H7A—C7—H7C | 109.5 | C16—C17—H17 | 119.7 |
H7B—C7—H7C | 109.5 | C18—C17—H17 | 119.7 |
C6—C8—C9 | 121.02 (15) | N1—C18—C17 | 120.15 (13) |
C6—C8—H8 | 119.5 | N1—C18—C13 | 121.39 (14) |
C9—C8—H8 | 119.5 | C17—C18—C13 | 118.44 (14) |
C8—C9—C3 | 120.57 (15) | C18—N1—C2 | 119.67 (12) |
C8—C9—H9 | 119.7 | C18—N1—H1N | 113.4 (13) |
C3—C9—H9 | 119.7 | C2—N1—H1N | 114.2 (13) |
N1—C2—C3—C4 | 122.88 (17) | C10—C11—C13—C14 | 175.01 (15) |
C10—C2—C3—C4 | −115.76 (17) | O12—C11—C13—C18 | −178.14 (16) |
N1—C2—C3—C9 | −56.54 (19) | C10—C11—C13—C18 | −2.7 (2) |
C10—C2—C3—C9 | 64.8 (2) | C18—C13—C14—C15 | 1.4 (2) |
C9—C3—C4—C5 | −0.9 (3) | C11—C13—C14—C15 | −176.33 (15) |
C2—C3—C4—C5 | 179.62 (17) | C13—C14—C15—C16 | −0.1 (3) |
C3—C4—C5—C6 | 1.0 (3) | C14—C15—C16—C17 | −0.6 (3) |
C4—C5—C6—C8 | −0.3 (3) | C15—C16—C17—C18 | 0.0 (2) |
C4—C5—C6—C7 | 179.37 (18) | C16—C17—C18—N1 | 179.75 (14) |
C5—C6—C8—C9 | −0.6 (3) | C16—C17—C18—C13 | 1.3 (2) |
C7—C6—C8—C9 | 179.79 (16) | C14—C13—C18—N1 | 179.63 (14) |
C6—C8—C9—C3 | 0.7 (3) | C11—C13—C18—N1 | −2.6 (2) |
C4—C3—C9—C8 | 0.1 (2) | C14—C13—C18—C17 | −1.9 (2) |
C2—C3—C9—C8 | 179.54 (15) | C11—C13—C18—C17 | 175.80 (14) |
N1—C2—C10—C11 | −48.91 (19) | C17—C18—N1—C2 | 160.66 (14) |
C3—C2—C10—C11 | −170.55 (14) | C13—C18—N1—C2 | −20.9 (2) |
C2—C10—C11—O12 | −155.13 (16) | C3—C2—N1—C18 | 168.89 (13) |
C2—C10—C11—C13 | 29.3 (2) | C10—C2—N1—C18 | 45.99 (19) |
O12—C11—C13—C14 | −0.4 (3) |
Cg1 and Cg2 are the centroids of the C13–C18 and C3–C9 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O12i | 0.88 (2) | 2.09 (2) | 2.9484 (17) | 166.9 (18) |
C4—H4···Cg1ii | 0.95 | 2.70 | 3.546 (2) | 149 |
C14—H14···Cg2iii | 0.95 | 2.80 | 3.617 (2) | 144 |
Symmetry codes: (i) x, −y, z−1/2; (ii) −x+1, −y, −z; (iii) x, −y, z+1/2. |
Cg1 and Cg2 are the centroids of the C13–C18 and C3–C9 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O12i | 0.88 (2) | 2.09 (2) | 2.9484 (17) | 166.9 (18) |
C4—H4···Cg1ii | 0.95 | 2.70 | 3.546 (2) | 149 |
C14—H14···Cg2iii | 0.95 | 2.80 | 3.617 (2) | 144 |
Symmetry codes: (i) x, −y, z−1/2; (ii) −x+1, −y, −z; (iii) x, −y, z+1/2. |
Acknowledgements
Thanks are due to MESRS (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique - Algeria) for financial support. We are grateful to Dr Thierry Roisnel of the Centre de difractométrie de Rennes, Université de Rennes 1, France, for technical assistance with the data collection.
References
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The role of heterocyclic compounds has become increasingly important in designing new classes of structural entities of medicinal importance. Quinolines are interesting synthetic targets because they act as building blocks for a large number of natural products (Hepworth, 1984). The formation of 2,3-dihydroquinolin-4(1H)-ones is generally accomplished by acid- or base-catalyzed isomerization of substituted 2'-aminochalcones (Donnelly & Farrell, 1990a,b; Tokes & Litkei, 1993). Most of these procedures involve the use of corrosive reagents such as orthophosphoric acid, acetic acid, or strong alkali. Many attempts have therefore been made to explore efficient catalysts to accelerate this reaction. Some of them are of limited synthetic scope due to low yields, long reaction times, and the need for a large amount of catalyst, specialized solvents (Tokes & Szilagyi, 1987; Tokes et al., 1992), or microwave activation (Kumar et al., 2004; Gordon, 2001; Olivier-Bourbigou & Magna, 2002). As part of our continuingeffort toward the development of new methods for the synthesis of biologically relevant heterocyclic compounds (Benzerka et al., 2012, 2013; Hayour et al., 2011), we have, recently, developed a procedure using butylmethylimidazolium(bmim).BF4 as a green solvent to provide an efficient and convenient protocol for the synthesis of 2,3-dihydroquinolin-4(1H)-ones from 2'-aminochalcones without the requirement for an additional catalyst (Chelghoum et al., 2012). We wish to describe herein the synthesis and single-crystal X-ray structure of 2-p-tolyl-2,3-dihydroquinolin-4(1H)-one (I). The molecular structure and the atom-numbering scheme of (I) are shown in Fig. 1. The molecule of consists of a dihydroquinolin-4(1H)-one moiety attached to tolyl group. The (1H)-dihydropyridine ring (C2/C10/C11/C13/C18/N1) is in a sofa conformation with atom C2 forming the flap. The dihedral angle between the two benzene rings (C3-C9/C13-C18) is 80.85 (8)°. The crystal packing can be described as alternating double layers parallel to (100) (Fig. 2). Intermolecular N—H···O hydrogen bonds (Fig.3; Table. 1) link the molecules along [100]. In addition, weak C—H···π interactions are observed.