organic compounds
2-(4-Chlorophenyl)-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 Chemie 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
The title molecule, C15H12ClNO, features a dihydroquinolin-4(1H)-one moiety attached to a chlorobenzene ring. The heterocyclic ring has a half-chair conformation with the methine C atom lying 0.574 (3) Å above the plane of the five remaining atoms (r.m.s. deviation = 0.0240 Å). The dihedral angles between the terminal benzene rings is 77.53 (9)°, indicating a significant twist in the molecule. In the crystal, supramolecular zigzag chains along the c-axis direction are sustained by N—H⋯O hydrogen bonds. These are connected into double chains by C—H⋯π interactions.
CCDC reference: 982789
Related literature
For background to and chemical reactivity of quinolone heterocycles, see: Diesbach & Kramer (1945); Prakash et al. (1994); Singh & Kapil (1993); Kalinin et al. (1992); Chauvin & Olivier (1996). For related structures, see: Bouraiou et al. (2008, 2011); Benzerka et al. (2011); Chelghoum et al. (2012).
Experimental
Crystal data
|
Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); 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).
Supporting information
CCDC reference: 982789
10.1107/S1600536814001548/tk5289sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001548/tk5289Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001548/tk5289Isup3.cml
The corresponding 2'-aminochalcone (0.5 mmol) and [bmim]BF4 (1 g) were heating at 150 °C for 2.5 h; bmim is butylmethylimidazolium. The crude product was isolated by repeated extraction with diethyl ether (7×10 ml). Filtration of the residue through a silica plug gave the 2-(4-chlorophenyl)-2,3-dihydroquinolin-4(1H)-one (I). 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.The C-bound H atoms were geometrically placed (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The H1N atom was refined with Uiso(H) = 1.2Ueq(N). Owing to poor agreement, the (1 1 0) reflection was omitted from the final cycles of refinement.
2-Arylquinolo-4-ones are nitrogen-containing analogues flavanones and flavones, and are characterized by a benzo ring fused to six-membered nitrogen containing heterocyclic ring with an aryl substituent at position 2. The quinolone heterocyclic ring has many reactive sites for possible transformation and can also result in different degree of unsaturation (Diesbach & Kramer, 1945; Prakash et al., 1994; Singh & Kapil, 1993; Kalinin et al., 1992). To date, numerous accounts have been reported in the literature for the synthesis of quinolone, due to their frequent occurrence in biologically interesting molecules. RTILs have proven to be viable reaction media for numerous types of reaction, including, for example, Friedel–Crafts alkylations, Diels–Alder, Knoevenagel, 1,3-dipolar cycloadditions, and in three component coupling reactions (Chauvin & Olivier, 1996). As a part of our program directed toward the synthesis of new suitably functionalized π interactions (Fig. 3; Table 1).
of potential biological activity (Bouraiou et al., 2008, 2011; Benzerka et al., 2011) and following our successes in the area of ionic liquid catalyzed 2-aminochalones isomerization into the corresponding 2-phenyl-2,3-dihydroquinolin-4(1H)-one (Chelghoum et al., 2012), we envisioned to get some information on the spatial arrangements of this type of compounds. We report herein the synthesis and single-crystal X-ray structure of 2-(4-chlorophenyl)-2,3-dihydroquinolin-4(1H)-one (I). The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1 and features a dihydroquinolin-4(1H)-one moiety attached to a chlorobenzene group. The crystal packing can be described as alternating double layers parallel to the (100) along the a axis (Fig. 2). It is stabilized by N—H···O hydrogen bonding and C—H···2-Arylquinolo-4-ones are nitrogen-containing analogues flavanones and flavones, and are characterized by a benzo ring fused to six-membered nitrogen containing heterocyclic ring with an aryl substituent at position 2. The quinolone heterocyclic ring has many reactive sites for possible transformation and can also result in different degree of unsaturation (Diesbach & Kramer, 1945; Prakash et al., 1994; Singh & Kapil, 1993; Kalinin et al., 1992). To date, numerous accounts have been reported in the literature for the synthesis of quinolone, due to their frequent occurrence in biologically interesting molecules. RTILs have proven to be viable reaction media for numerous types of reaction, including, for example, Friedel–Crafts alkylations, Diels–Alder, Knoevenagel, 1,3-dipolar cycloadditions, and in three component coupling reactions (Chauvin & Olivier, 1996). As a part of our program directed toward the synthesis of new suitably functionalized π interactions (Fig. 3; Table 1).
of potential biological activity (Bouraiou et al., 2008, 2011; Benzerka et al., 2011) and following our successes in the area of ionic liquid catalyzed 2-aminochalones isomerization into the corresponding 2-phenyl-2,3-dihydroquinolin-4(1H)-one (Chelghoum et al., 2012), we envisioned to get some information on the spatial arrangements of this type of compounds. We report herein the synthesis and single-crystal X-ray structure of 2-(4-chlorophenyl)-2,3-dihydroquinolin-4(1H)-one (I). The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1 and features a dihydroquinolin-4(1H)-one moiety attached to a chlorobenzene group. The crystal packing can be described as alternating double layers parallel to the (100) along the a axis (Fig. 2). It is stabilized by N—H···O hydrogen bonding and C—H···For background to and chemical reactivity of quinolone heterocycles, see: Diesbach & Kramer (1945); Prakash et al. (1994); Singh & Kapil (1993); Kalinin et al. (1992); Chauvin & Olivier (1996). For related structures, see: Bouraiou et al. (2008, 2011); Benzerka et al. (2011).
The corresponding 2'-aminochalcone (0.5 mmol) and [bmim]BF4 (1 g) were heating at 150 °C for 2.5 h; bmim is butylmethylimidazolium. The crude product was isolated by repeated extraction with diethyl ether (7×10 ml). Filtration of the residue through a silica plug gave the 2-(4-chlorophenyl)-2,3-dihydroquinolin-4(1H)-one (I). 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. detailsThe C-bound H atoms were geometrically placed (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C). The H1N atom was refined with Uiso(H) = 1.2Ueq(N). Owing to poor agreement, the (1 1 0) reflection was omitted from the final cycles of refinement.
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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).Fig. 1. The molecular geometry of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radius. | |
Fig. 2. Alternating double layers parallel to (100) in (I), viewed down the c axis. | |
Fig. 3. A diagram of the layered crystal packing of (I), viewed down the b axis showing hydrogen bonds as dashed lines. |
C15H12ClNO | F(000) = 1072 |
Mr = 257.71 | Dx = 1.366 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5286 reflections |
a = 17.703 (2) Å | θ = 2.4–27.2° |
b = 10.7537 (17) Å | µ = 0.29 mm−1 |
c = 13.658 (2) Å | T = 150 K |
β = 105.486 (6)° | Prism, colourless |
V = 2505.8 (6) Å3 | 0.17 × 0.12 × 0.06 mm |
Z = 8 |
Bruker APEXII diffractometer | 2314 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
CCD rotation images, thin slices scans | θmax = 27.5°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −22→21 |
Tmin = 0.932, Tmax = 0.983 | k = −13→13 |
15688 measured reflections | l = −16→17 |
2852 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0328P)2 + 4.0966P] where P = (Fo2 + 2Fc2)/3 |
2852 reflections | (Δ/σ)max = 0.001 |
166 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C15H12ClNO | V = 2505.8 (6) Å3 |
Mr = 257.71 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 17.703 (2) Å | µ = 0.29 mm−1 |
b = 10.7537 (17) Å | T = 150 K |
c = 13.658 (2) Å | 0.17 × 0.12 × 0.06 mm |
β = 105.486 (6)° |
Bruker APEXII diffractometer | 2852 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 2314 reflections with I > 2σ(I) |
Tmin = 0.932, Tmax = 0.983 | Rint = 0.037 |
15688 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.53 e Å−3 |
2852 reflections | Δρmin = −0.39 e Å−3 |
166 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 | ||
C1 | 0.14660 (10) | 1.07351 (16) | 0.61189 (13) | 0.0207 (4) | |
C2 | 0.17699 (11) | 1.17882 (17) | 0.57430 (14) | 0.0245 (4) | |
H2 | 0.1876 | 1.1752 | 0.5112 | 0.029* | |
C3 | 0.19115 (11) | 1.28710 (18) | 0.63005 (15) | 0.0281 (4) | |
H3 | 0.2118 | 1.3555 | 0.6044 | 0.034* | |
C4 | 0.17487 (12) | 1.29588 (18) | 0.72502 (15) | 0.0307 (4) | |
H4 | 0.1839 | 1.3697 | 0.7618 | 0.037* | |
C5 | 0.14538 (11) | 1.19394 (18) | 0.76280 (14) | 0.0283 (4) | |
H5 | 0.1343 | 1.1994 | 0.8255 | 0.034* | |
C6 | 0.13150 (10) | 1.08117 (16) | 0.70848 (13) | 0.0225 (4) | |
C7 | 0.10478 (11) | 0.97037 (18) | 0.75251 (13) | 0.0271 (4) | |
C8 | 0.09756 (12) | 0.85216 (18) | 0.69154 (13) | 0.0282 (4) | |
H8A | 0.0563 | 0.8016 | 0.7056 | 0.034* | |
H8B | 0.1462 | 0.806 | 0.7138 | 0.034* | |
C9 | 0.07953 (11) | 0.87276 (17) | 0.57716 (13) | 0.0256 (4) | |
H9 | 0.0258 | 0.904 | 0.5523 | 0.031* | |
C10 | 0.08698 (11) | 0.75256 (16) | 0.52145 (13) | 0.0241 (4) | |
C11 | 0.02108 (12) | 0.69804 (18) | 0.45834 (15) | 0.0315 (4) | |
H11 | −0.0276 | 0.7351 | 0.4508 | 0.038* | |
C12 | 0.02618 (12) | 0.58890 (19) | 0.40597 (16) | 0.0329 (5) | |
H12 | −0.0186 | 0.5527 | 0.364 | 0.04* | |
C13 | 0.09869 (11) | 0.53526 (16) | 0.41728 (14) | 0.0264 (4) | |
C14 | 0.16620 (11) | 0.58739 (18) | 0.47938 (14) | 0.0277 (4) | |
H14 | 0.2148 | 0.5505 | 0.4858 | 0.033* | |
C15 | 0.15978 (11) | 0.69599 (18) | 0.53192 (14) | 0.0274 (4) | |
H15 | 0.2045 | 0.7314 | 0.5746 | 0.033* | |
N1 | 0.13339 (9) | 0.96526 (14) | 0.55585 (11) | 0.0224 (3) | |
H1N | 0.1307 (12) | 0.9735 (19) | 0.4941 (16) | 0.027* | |
O1 | 0.09352 (10) | 0.96926 (14) | 0.83773 (10) | 0.0422 (4) | |
Cl1 | 0.10656 (4) | 0.39956 (5) | 0.35097 (4) | 0.04532 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0211 (8) | 0.0223 (9) | 0.0191 (8) | 0.0041 (7) | 0.0061 (7) | 0.0013 (7) |
C2 | 0.0264 (9) | 0.0259 (9) | 0.0238 (9) | 0.0020 (7) | 0.0112 (7) | 0.0023 (7) |
C3 | 0.0274 (10) | 0.0244 (9) | 0.0338 (10) | −0.0023 (8) | 0.0103 (8) | 0.0022 (8) |
C4 | 0.0348 (11) | 0.0257 (10) | 0.0300 (10) | −0.0025 (8) | 0.0060 (8) | −0.0080 (8) |
C5 | 0.0340 (11) | 0.0308 (10) | 0.0197 (9) | −0.0009 (8) | 0.0068 (8) | −0.0045 (7) |
C6 | 0.0258 (9) | 0.0243 (9) | 0.0168 (8) | 0.0013 (7) | 0.0048 (7) | −0.0003 (7) |
C7 | 0.0368 (11) | 0.0291 (10) | 0.0161 (8) | −0.0002 (8) | 0.0083 (7) | 0.0010 (7) |
C8 | 0.0415 (11) | 0.0256 (9) | 0.0203 (9) | −0.0012 (8) | 0.0133 (8) | 0.0025 (7) |
C9 | 0.0315 (10) | 0.0250 (9) | 0.0224 (9) | 0.0014 (7) | 0.0106 (7) | 0.0013 (7) |
C10 | 0.0345 (10) | 0.0206 (9) | 0.0210 (8) | 0.0002 (7) | 0.0142 (7) | 0.0013 (7) |
C11 | 0.0282 (10) | 0.0289 (10) | 0.0377 (11) | 0.0059 (8) | 0.0092 (8) | −0.0023 (8) |
C12 | 0.0286 (10) | 0.0291 (10) | 0.0370 (11) | 0.0013 (8) | 0.0017 (8) | −0.0054 (8) |
C13 | 0.0367 (10) | 0.0182 (9) | 0.0253 (9) | 0.0036 (7) | 0.0098 (8) | −0.0026 (7) |
C14 | 0.0260 (9) | 0.0271 (10) | 0.0305 (10) | 0.0054 (8) | 0.0085 (8) | 0.0040 (8) |
C15 | 0.0272 (10) | 0.0296 (10) | 0.0244 (9) | −0.0061 (8) | 0.0049 (7) | −0.0003 (7) |
N1 | 0.0332 (8) | 0.0215 (8) | 0.0154 (7) | 0.0008 (6) | 0.0118 (6) | 0.0012 (6) |
O1 | 0.0737 (11) | 0.0384 (8) | 0.0198 (7) | −0.0086 (8) | 0.0219 (7) | −0.0018 (6) |
Cl1 | 0.0608 (4) | 0.0271 (3) | 0.0468 (3) | 0.0075 (2) | 0.0122 (3) | −0.0135 (2) |
C1—N1 | 1.378 (2) | C8—H8B | 0.97 |
C1—C2 | 1.408 (2) | C9—N1 | 1.460 (2) |
C1—C6 | 1.417 (2) | C9—C10 | 1.523 (2) |
C2—C3 | 1.377 (3) | C9—H9 | 0.98 |
C2—H2 | 0.93 | C10—C11 | 1.382 (3) |
C3—C4 | 1.405 (3) | C10—C15 | 1.398 (3) |
C3—H3 | 0.93 | C11—C12 | 1.390 (3) |
C4—C5 | 1.373 (3) | C11—H11 | 0.93 |
C4—H4 | 0.93 | C12—C13 | 1.378 (3) |
C5—C6 | 1.409 (2) | C12—H12 | 0.93 |
C5—H5 | 0.93 | C13—C14 | 1.386 (3) |
C6—C7 | 1.469 (3) | C13—Cl1 | 1.7425 (18) |
C7—O1 | 1.232 (2) | C14—C15 | 1.391 (3) |
C7—C8 | 1.506 (3) | C14—H14 | 0.93 |
C8—C9 | 1.525 (2) | C15—H15 | 0.93 |
C8—H8A | 0.97 | N1—H1N | 0.84 (2) |
N1—C1—C2 | 120.10 (15) | N1—C9—C10 | 109.29 (14) |
N1—C1—C6 | 121.33 (15) | N1—C9—C8 | 109.52 (15) |
C2—C1—C6 | 118.56 (16) | C10—C9—C8 | 111.48 (15) |
C3—C2—C1 | 120.62 (16) | N1—C9—H9 | 108.8 |
C3—C2—H2 | 119.7 | C10—C9—H9 | 108.8 |
C1—C2—H2 | 119.7 | C8—C9—H9 | 108.8 |
C2—C3—C4 | 121.02 (17) | C11—C10—C15 | 118.75 (17) |
C2—C3—H3 | 119.5 | C11—C10—C9 | 120.02 (17) |
C4—C3—H3 | 119.5 | C15—C10—C9 | 121.23 (17) |
C5—C4—C3 | 119.06 (17) | C10—C11—C12 | 121.28 (18) |
C5—C4—H4 | 120.5 | C10—C11—H11 | 119.4 |
C3—C4—H4 | 120.5 | C12—C11—H11 | 119.4 |
C4—C5—C6 | 121.32 (17) | C13—C12—C11 | 118.85 (18) |
C4—C5—H5 | 119.3 | C13—C12—H12 | 120.6 |
C6—C5—H5 | 119.3 | C11—C12—H12 | 120.6 |
C5—C6—C1 | 119.40 (16) | C12—C13—C14 | 121.64 (17) |
C5—C6—C7 | 120.84 (16) | C12—C13—Cl1 | 119.59 (15) |
C1—C6—C7 | 119.71 (16) | C14—C13—Cl1 | 118.77 (15) |
O1—C7—C6 | 123.07 (17) | C13—C14—C15 | 118.64 (17) |
O1—C7—C8 | 120.19 (17) | C13—C14—H14 | 120.7 |
C6—C7—C8 | 116.57 (15) | C15—C14—H14 | 120.7 |
C7—C8—C9 | 114.05 (15) | C14—C15—C10 | 120.85 (17) |
C7—C8—H8A | 108.7 | C14—C15—H15 | 119.6 |
C9—C8—H8A | 108.7 | C10—C15—H15 | 119.6 |
C7—C8—H8B | 108.7 | C1—N1—C9 | 119.19 (14) |
C9—C8—H8B | 108.7 | C1—N1—H1N | 115.2 (15) |
H8A—C8—H8B | 107.6 | C9—N1—H1N | 114.2 (14) |
N1—C1—C2—C3 | −179.37 (16) | N1—C9—C10—C11 | −126.55 (18) |
C6—C1—C2—C3 | −0.5 (3) | C8—C9—C10—C11 | 112.2 (2) |
C1—C2—C3—C4 | −0.7 (3) | N1—C9—C10—C15 | 52.8 (2) |
C2—C3—C4—C5 | 0.9 (3) | C8—C9—C10—C15 | −68.4 (2) |
C3—C4—C5—C6 | 0.2 (3) | C15—C10—C11—C12 | 0.1 (3) |
C4—C5—C6—C1 | −1.4 (3) | C9—C10—C11—C12 | 179.52 (18) |
C4—C5—C6—C7 | 176.00 (18) | C10—C11—C12—C13 | −0.4 (3) |
N1—C1—C6—C5 | −179.59 (16) | C11—C12—C13—C14 | 0.0 (3) |
C2—C1—C6—C5 | 1.5 (3) | C11—C12—C13—Cl1 | −179.13 (15) |
N1—C1—C6—C7 | 3.0 (3) | C12—C13—C14—C15 | 0.6 (3) |
C2—C1—C6—C7 | −175.94 (16) | Cl1—C13—C14—C15 | 179.75 (14) |
C5—C6—C7—O1 | −0.3 (3) | C13—C14—C15—C10 | −0.8 (3) |
C1—C6—C7—O1 | 177.09 (18) | C11—C10—C15—C14 | 0.5 (3) |
C5—C6—C7—C8 | −175.52 (17) | C9—C10—C15—C14 | −178.88 (16) |
C1—C6—C7—C8 | 1.9 (3) | C2—C1—N1—C9 | −159.94 (16) |
O1—C7—C8—C9 | 156.11 (19) | C6—C1—N1—C9 | 21.2 (2) |
C6—C7—C8—C9 | −28.6 (2) | C10—C9—N1—C1 | −168.81 (15) |
C7—C8—C9—N1 | 49.0 (2) | C8—C9—N1—C1 | −46.4 (2) |
C7—C8—C9—C10 | 170.10 (16) |
Cg2 and Cg3 are the centroids of the C1–C6 and C10–C15 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.84 (2) | 2.15 (2) | 2.957 (2) | 162 (2) |
C5—H5···Cg3ii | 0.93 | 2.83 | 3.641 (2) | 146 |
C11—H11···Cg2iii | 0.93 | 2.63 | 3.465 (2) | 149 |
Symmetry codes: (i) x, −y+2, z−1/2; (ii) −x+1/2, y+5/2, −z+1/2; (iii) x+1/2, y+5/2, z+1. |
Cg2 and Cg3 are the centroids of the C1–C6 and C10–C15 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.84 (2) | 2.15 (2) | 2.957 (2) | 162 (2) |
C5—H5···Cg3ii | 0.93 | 2.83 | 3.641 (2) | 146 |
C11—H11···Cg2iii | 0.93 | 2.63 | 3.465 (2) | 149 |
Symmetry codes: (i) x, −y+2, z−1/2; (ii) −x+1/2, y+5/2, −z+1/2; (iii) x+1/2, y+5/2, z+1. |
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 Roisnel Thierry from the Centre de difractométrie de Rennes, Université de Rennes 1, France, for his technical assistance with the data collection.
References
Benzerka, S., Bouraiou, A., Bouacida, S., Roisnel, T. & Belfaitah, A. (2011). Acta Cryst. E67, o2084–o2085. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bouraiou, A., Berrée, F., Bouacida, S., Carboni, C., Debache, A., Roisnel, T. & Belfaitah, A. (2011). Lett. Org. Chem. 8, 474–477. CSD CrossRef Google Scholar
Bouraiou, A., Debbache, A., Rhouati, S., Carboni, B. & Belfaitah, A. (2008). J. Heterocycl. Chem. 45, 329–333. CrossRef CAS Google Scholar
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany. Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Chauvin, Y. & Olivier, H. (1996). In Applied Homogeneous Catalysis with Organometallic Compounds, edited by B. Cornils & W. A. Herrmann, Vol. 1, p. 245. New York: Wiley-VCH. Google Scholar
Chelghoum, M., Bahnous, M., Bouraiou, A., Bouacida, S. & Belfaitah, A. (2012). Tetrahedron Lett. 53, 4059–4061. Web of Science CSD CrossRef CAS Google Scholar
Diesbach, H. & Kramer, H. (1945). Helv. Chim. Acta, 28, 1399–1405. PubMed Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kalinin, V. N., Shostakovsky, M. V. & Ponomaryov, A. B. (1992). Tetrahedron Lett. 33, 373–376. CrossRef CAS Web of Science Google Scholar
Prakash, O., Kumar, D., Saini, R. K. & Singh, S. P. (1994). Synth. Commun. 24, 2167–2172. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, O. V. & Kapil, R. S. (1993). Synth. Commun. 23, 277–283. CrossRef CAS Web of Science Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.