organic compounds
(2E,2′E)-1,1′-Bis(6-chloro-2-methyl-4-phenylquinolin-3-yl)-3,3′-(1,4-phenylene)diprop-2-en-1-one ethyl acetate disolvate
aLaboratoire de Chimie Appliquée, Faculté des Sciences, Université de Guelma 24000, Algeria, bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, 25000 Algeria, cCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France, and dLaboratoire des Produits Naturels, d'Origine Végétale et de Synthèse Organique, PHYSYNOR, Université Mentouri-Constantine, 25000 Constantine, Algeria
*Correspondence e-mail: bouacida_sofiane@yahoo.fr
In the title solvate, C44H30Cl2N2O2·2C4H8O2, the complete polycyclic molecule is generated by inversion symmetry. The dihedral angle between the quinolyl ring system (Q; r.m.s. deviation = 0.020 Å) and the pendant phenyl ring is 78.80 (6)°; the dihedral angle between Q and the central benzene ring is 85.92 (7)°. In the crystal, the components are linked by C—H⋯O and C—H⋯π interactions, generating (110) layers. Weak aromatic π–π stacking [centroid–centroid distances = 3.7025 (11) and 3.8124 (10) Å] is also observed.
Related literature
For our previous studies in the area of potentially bioactive molecules, see: Menasra et al. (2005); Kedjadja et al. (2004). For further synthetic details, see: Wang et al. (2006).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (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 (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
https://doi.org/10.1107/S1600536812049422/hb7004sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049422/hb7004Isup2.hkl
A mixture of 2-aminobenzophénone (1.0 mmol), acetylacetone (1.2 mmol), water (1 ml) and 1.0 eq. of 1 N HCl, gave the corresponding 1-(2-methyl-4-phenylquinolin-3-yl) ethanone as a white solid in 86% yield, according to the procedure reported by Wang et al. (2006). Next, the title compound was prepared in 75% of yield, by an aldol condensation reaction of the Friedländer product with 0.5 eq. of terephthalaldehyde in an ethanolic solution of NaOH at room temperature. Colourless prisms of (I) were obtained by crystallization from ethyl acetate/petroleum ether (1/1) solution.
Approximate positions for all the H atoms were first obtained from the difference
However, the H atoms were situated into idealized positions and the H-atoms have been refined within the riding atom approximation. The applied constraints were as follow: Caryl—Haryl = 0.95 Å; Cmethylene—Hmethylene = 0.99 Å and Cmethyl—Hmethyl = 0.98 Å and; 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 or Hmethylene) = 1.2 Ueq(Caryl or Cmethylene).In continuation of our interest related to the synthesis and structures of potentially bioactive products (Kedjadja et al. 2004; Menasra et al. 2005), we report herein the synthesis and the
of the title compound, (I). The reactivity of this compound and its analogues toward nucleophiles is under investigation.The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. The π interactions (Table. 1) and strong π-π stacking interactions between quinolyl rings with a centroid-centroid distance of 3.7025 (11) and 3.8124 (10)å. These interactions link the molecules within the layers and also link the layers together, reinforcing the cohesion of the structure.
of (I)consists of one-half of the molecule, with the other half generated by a crystallographic inversion centre. In the title molecule the centrosymmetric phenyl ring is attached to two prop-2-en-1-one linked to two 6-chloro-2-methyl-4-phenylquinolin-3-yl and two molecules of ethyl acetate are co-crystalized with it. The two rings of quinolyl group are fused in axial fashion and form adihedral angle of 1.72 (5)° and this quasi plane system forms a dihedral angle of 78.80 (6)° with the phenyl ring (C12—C17) attached to quinolyl moiety. The crystal packing can be described as layers in zigzag parallel to the (110) plane. (Fig. 2). It features C—H···O and C—H···For our previous studies in the area of potentially bioactive molecules, see: Menasra et al. (2005); Kedjadja et al. (2004). For further synthetic details, see: Wang et al. (2006).
Data collection: APEX2 (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 (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012).C44H30Cl2N2O2·2C4H8O2 | Z = 1 |
Mr = 865.81 | F(000) = 454 |
Triclinic, P1 | Dx = 1.315 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.9851 (3) Å | Cell parameters from 8289 reflections |
b = 10.0086 (2) Å | θ = 2.5–27.5° |
c = 11.3676 (3) Å | µ = 0.20 mm−1 |
α = 102.350 (1)° | T = 150 K |
β = 97.108 (1)° | Prism, colourless |
γ = 95.290 (2)° | 0.25 × 0.15 × 0.1 mm |
V = 1092.94 (5) Å3 |
Bruker APEXII diffractometer | 4035 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
CCD rotation images, thin slices scans | θmax = 27.5°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −12→12 |
Tmin = 0.884, Tmax = 0.980 | k = −12→12 |
18119 measured reflections | l = −14→14 |
4866 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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0694P)2 + 0.8188P] where P = (Fo2 + 2Fc2)/3 |
4866 reflections | (Δ/σ)max = 0.011 |
283 parameters | Δρmax = 1.02 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
C44H30Cl2N2O2·2C4H8O2 | γ = 95.290 (2)° |
Mr = 865.81 | V = 1092.94 (5) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.9851 (3) Å | Mo Kα radiation |
b = 10.0086 (2) Å | µ = 0.20 mm−1 |
c = 11.3676 (3) Å | T = 150 K |
α = 102.350 (1)° | 0.25 × 0.15 × 0.1 mm |
β = 97.108 (1)° |
Bruker APEXII diffractometer | 4866 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 4035 reflections with I > 2σ(I) |
Tmin = 0.884, Tmax = 0.980 | Rint = 0.026 |
18119 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.04 | Δρmax = 1.02 e Å−3 |
4866 reflections | Δρmin = −0.42 e Å−3 |
283 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 | ||
O53 | 0.31158 (16) | 0.42524 (16) | 0.11802 (16) | 0.0417 (4) | |
Cl1 | 0.31876 (5) | 0.75570 (5) | 0.69990 (4) | 0.02960 (15) | |
C1 | 0.23208 (18) | 0.65060 (19) | 0.56441 (16) | 0.0234 (4) | |
C2 | 0.15254 (19) | 0.70928 (19) | 0.48229 (18) | 0.0265 (4) | |
H2 | 0.1473 | 0.8057 | 0.4995 | 0.032* | |
C3 | 0.08296 (19) | 0.6252 (2) | 0.37739 (18) | 0.0265 (4) | |
H3 | 0.0294 | 0.6642 | 0.3215 | 0.032* | |
C4 | 0.08921 (18) | 0.48125 (18) | 0.35046 (16) | 0.0220 (4) | |
C5 | 0.17208 (17) | 0.42485 (18) | 0.43299 (16) | 0.0209 (4) | |
C6 | 0.24378 (18) | 0.51286 (18) | 0.54149 (16) | 0.0226 (4) | |
H6 | 0.2995 | 0.4763 | 0.5978 | 0.027* | |
N7 | 0.01376 (16) | 0.40156 (16) | 0.24584 (14) | 0.0248 (3) | |
C8 | 0.01928 (18) | 0.26750 (19) | 0.22137 (16) | 0.0232 (4) | |
C9 | −0.0649 (2) | 0.1817 (2) | 0.10685 (18) | 0.0309 (4) | |
H9A | −0.1169 | 0.2411 | 0.0654 | 0.046* | |
H9B | −0.1277 | 0.112 | 0.1274 | 0.046* | |
H9C | −0.0051 | 0.1361 | 0.0531 | 0.046* | |
C10 | 0.10213 (17) | 0.20250 (18) | 0.29886 (16) | 0.0210 (4) | |
C11 | 0.17907 (17) | 0.28022 (18) | 0.40423 (16) | 0.0206 (4) | |
C12 | 0.26671 (18) | 0.21649 (18) | 0.48762 (16) | 0.0214 (4) | |
C13 | 0.20937 (19) | 0.14663 (19) | 0.56647 (18) | 0.0262 (4) | |
H13 | 0.1138 | 0.1385 | 0.5664 | 0.031* | |
C14 | 0.2911 (2) | 0.0889 (2) | 0.64504 (18) | 0.0300 (4) | |
H14 | 0.2515 | 0.0424 | 0.6993 | 0.036* | |
C15 | 0.4301 (2) | 0.0989 (2) | 0.64447 (18) | 0.0305 (4) | |
H15 | 0.4858 | 0.0584 | 0.6976 | 0.037* | |
C16 | 0.4880 (2) | 0.1681 (2) | 0.56644 (19) | 0.0303 (4) | |
H16 | 0.5834 | 0.1745 | 0.5658 | 0.036* | |
C17 | 0.40700 (19) | 0.2279 (2) | 0.48915 (17) | 0.0265 (4) | |
H17 | 0.4474 | 0.2769 | 0.437 | 0.032* | |
C18 | 0.10551 (18) | 0.04827 (18) | 0.26507 (16) | 0.0228 (4) | |
O19 | 0.02241 (15) | −0.02933 (15) | 0.29611 (15) | 0.0380 (4) | |
C20 | 0.21001 (18) | −0.00520 (18) | 0.19329 (16) | 0.0218 (4) | |
H20 | 0.2189 | −0.1008 | 0.1793 | 0.026* | |
C21 | 0.29293 (17) | 0.07597 (18) | 0.14703 (15) | 0.0202 (3) | |
H21 | 0.2831 | 0.1714 | 0.1651 | 0.024* | |
C22 | 0.39718 (17) | 0.03406 (17) | 0.07162 (15) | 0.0191 (3) | |
C23 | 0.47009 (18) | 0.13423 (18) | 0.02708 (16) | 0.0216 (4) | |
H23 | 0.4496 | 0.2266 | 0.0455 | 0.026* | |
C24 | 0.57142 (18) | 0.10142 (18) | −0.04320 (16) | 0.0218 (4) | |
H24 | 0.6197 | 0.1711 | −0.0722 | 0.026* | |
C51 | 0.5390 (2) | 0.5546 (3) | 0.1748 (2) | 0.0432 (5) | |
H51A | 0.5797 | 0.4728 | 0.139 | 0.065* | |
H51B | 0.6037 | 0.6128 | 0.2421 | 0.065* | |
H51C | 0.5165 | 0.6066 | 0.1127 | 0.065* | |
C52 | 0.4113 (2) | 0.5106 (2) | 0.2220 (2) | 0.0398 (5) | |
H52A | 0.4331 | 0.4563 | 0.2836 | 0.048* | |
H52B | 0.3716 | 0.5928 | 0.2611 | 0.048* | |
C54 | 0.2331 (2) | 0.4949 (3) | 0.0581 (2) | 0.0412 (5) | |
C55 | 0.1442 (3) | 0.3999 (3) | −0.0465 (2) | 0.0465 (6) | |
H55A | 0.0557 | 0.376 | −0.0225 | 0.07* | |
H55B | 0.1867 | 0.3159 | −0.0712 | 0.07* | |
H55C | 0.1314 | 0.4451 | −0.1148 | 0.07* | |
O56 | 0.23575 (18) | 0.61974 (16) | 0.08844 (18) | 0.0503 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O53 | 0.0426 (9) | 0.0300 (8) | 0.0574 (10) | 0.0100 (7) | 0.0142 (8) | 0.0142 (7) |
Cl1 | 0.0318 (3) | 0.0239 (2) | 0.0291 (2) | 0.00118 (18) | 0.00172 (18) | −0.00038 (18) |
C1 | 0.0207 (9) | 0.0231 (9) | 0.0252 (9) | 0.0010 (7) | 0.0050 (7) | 0.0024 (7) |
C2 | 0.0250 (9) | 0.0198 (8) | 0.0357 (10) | 0.0050 (7) | 0.0068 (8) | 0.0062 (8) |
C3 | 0.0255 (9) | 0.0245 (9) | 0.0312 (10) | 0.0074 (7) | 0.0035 (7) | 0.0087 (8) |
C4 | 0.0207 (9) | 0.0222 (9) | 0.0243 (9) | 0.0045 (7) | 0.0069 (7) | 0.0054 (7) |
C5 | 0.0192 (8) | 0.0214 (8) | 0.0233 (8) | 0.0034 (7) | 0.0068 (6) | 0.0055 (7) |
C6 | 0.0227 (9) | 0.0218 (9) | 0.0243 (9) | 0.0035 (7) | 0.0045 (7) | 0.0061 (7) |
N7 | 0.0240 (8) | 0.0257 (8) | 0.0248 (8) | 0.0056 (6) | 0.0037 (6) | 0.0052 (6) |
C8 | 0.0208 (9) | 0.0266 (9) | 0.0229 (9) | 0.0030 (7) | 0.0069 (7) | 0.0048 (7) |
C9 | 0.0328 (10) | 0.0299 (10) | 0.0268 (10) | 0.0058 (8) | −0.0002 (8) | 0.0012 (8) |
C10 | 0.0190 (8) | 0.0221 (8) | 0.0240 (8) | 0.0030 (7) | 0.0103 (7) | 0.0056 (7) |
C11 | 0.0197 (8) | 0.0214 (8) | 0.0229 (8) | 0.0038 (7) | 0.0089 (6) | 0.0064 (7) |
C12 | 0.0234 (9) | 0.0180 (8) | 0.0228 (8) | 0.0045 (7) | 0.0051 (7) | 0.0031 (7) |
C13 | 0.0248 (9) | 0.0239 (9) | 0.0328 (10) | 0.0042 (7) | 0.0091 (7) | 0.0095 (8) |
C14 | 0.0374 (11) | 0.0252 (9) | 0.0314 (10) | 0.0062 (8) | 0.0088 (8) | 0.0121 (8) |
C15 | 0.0362 (11) | 0.0261 (9) | 0.0293 (10) | 0.0108 (8) | 0.0001 (8) | 0.0063 (8) |
C16 | 0.0225 (9) | 0.0315 (10) | 0.0362 (11) | 0.0067 (8) | 0.0039 (8) | 0.0053 (8) |
C17 | 0.0247 (9) | 0.0285 (10) | 0.0291 (9) | 0.0051 (7) | 0.0088 (7) | 0.0092 (8) |
C18 | 0.0231 (9) | 0.0224 (9) | 0.0229 (8) | 0.0018 (7) | 0.0065 (7) | 0.0036 (7) |
O19 | 0.0385 (8) | 0.0268 (7) | 0.0525 (9) | −0.0009 (6) | 0.0267 (7) | 0.0083 (7) |
C20 | 0.0237 (9) | 0.0189 (8) | 0.0227 (8) | 0.0041 (7) | 0.0053 (7) | 0.0029 (7) |
C21 | 0.0211 (8) | 0.0188 (8) | 0.0200 (8) | 0.0041 (6) | 0.0040 (6) | 0.0019 (6) |
C22 | 0.0189 (8) | 0.0198 (8) | 0.0184 (8) | 0.0036 (6) | 0.0027 (6) | 0.0032 (6) |
C23 | 0.0237 (9) | 0.0167 (8) | 0.0252 (9) | 0.0050 (7) | 0.0061 (7) | 0.0041 (7) |
C24 | 0.0235 (9) | 0.0183 (8) | 0.0249 (9) | 0.0025 (7) | 0.0076 (7) | 0.0058 (7) |
C51 | 0.0440 (13) | 0.0422 (13) | 0.0419 (13) | 0.0048 (10) | 0.0016 (10) | 0.0096 (10) |
C52 | 0.0454 (13) | 0.0374 (12) | 0.0354 (11) | 0.0053 (10) | −0.0002 (9) | 0.0090 (9) |
C54 | 0.0376 (12) | 0.0418 (13) | 0.0482 (13) | 0.0055 (10) | 0.0113 (10) | 0.0158 (11) |
C55 | 0.0407 (13) | 0.0438 (13) | 0.0527 (14) | −0.0015 (10) | −0.0001 (11) | 0.0131 (11) |
O56 | 0.0483 (10) | 0.0284 (8) | 0.0802 (13) | 0.0103 (7) | 0.0120 (9) | 0.0216 (8) |
O53—C54 | 1.318 (3) | C15—C16 | 1.384 (3) |
O53—C52 | 1.496 (3) | C15—H15 | 0.95 |
Cl1—C1 | 1.7427 (18) | C16—C17 | 1.387 (3) |
C1—C6 | 1.366 (3) | C16—H16 | 0.95 |
C1—C2 | 1.409 (3) | C17—H17 | 0.95 |
C2—C3 | 1.368 (3) | C18—O19 | 1.219 (2) |
C2—H2 | 0.95 | C18—C20 | 1.472 (2) |
C3—C4 | 1.417 (3) | C20—C21 | 1.337 (2) |
C3—H3 | 0.95 | C20—H20 | 0.95 |
C4—N7 | 1.371 (2) | C21—C22 | 1.464 (2) |
C4—C5 | 1.416 (3) | C21—H21 | 0.95 |
C5—C6 | 1.418 (2) | C22—C24i | 1.399 (2) |
C5—C11 | 1.424 (2) | C22—C23 | 1.402 (2) |
C6—H6 | 0.95 | C23—C24 | 1.385 (2) |
N7—C8 | 1.319 (2) | C23—H23 | 0.95 |
C8—C10 | 1.431 (3) | C24—C22i | 1.399 (2) |
C8—C9 | 1.502 (3) | C24—H24 | 0.95 |
C9—H9A | 0.98 | C51—C52 | 1.507 (3) |
C9—H9B | 0.98 | C51—H51A | 0.98 |
C9—H9C | 0.98 | C51—H51B | 0.98 |
C10—C11 | 1.376 (2) | C51—H51C | 0.98 |
C10—C18 | 1.513 (2) | C52—H52A | 0.99 |
C11—C12 | 1.493 (2) | C52—H52B | 0.99 |
C12—C17 | 1.393 (3) | C54—O56 | 1.219 (3) |
C12—C13 | 1.393 (3) | C54—C55 | 1.485 (3) |
C13—C14 | 1.388 (3) | C55—H55A | 0.98 |
C13—H13 | 0.95 | C55—H55B | 0.98 |
C14—C15 | 1.383 (3) | C55—H55C | 0.98 |
C14—H14 | 0.95 | ||
C54—O53—C52 | 115.38 (17) | C16—C15—H15 | 120 |
C6—C1—C2 | 122.05 (17) | C15—C16—C17 | 120.13 (18) |
C6—C1—Cl1 | 118.43 (14) | C15—C16—H16 | 119.9 |
C2—C1—Cl1 | 119.52 (14) | C17—C16—H16 | 119.9 |
C3—C2—C1 | 118.92 (17) | C16—C17—C12 | 120.35 (17) |
C3—C2—H2 | 120.5 | C16—C17—H17 | 119.8 |
C1—C2—H2 | 120.5 | C12—C17—H17 | 119.8 |
C2—C3—C4 | 121.30 (17) | O19—C18—C20 | 121.15 (16) |
C2—C3—H3 | 119.4 | O19—C18—C10 | 120.30 (15) |
C4—C3—H3 | 119.4 | C20—C18—C10 | 118.54 (15) |
N7—C4—C5 | 122.46 (16) | C21—C20—C18 | 122.36 (16) |
N7—C4—C3 | 118.70 (16) | C21—C20—H20 | 118.8 |
C5—C4—C3 | 118.84 (16) | C18—C20—H20 | 118.8 |
C4—C5—C6 | 119.40 (16) | C20—C21—C22 | 127.20 (16) |
C4—C5—C11 | 118.38 (16) | C20—C21—H21 | 116.4 |
C6—C5—C11 | 122.22 (16) | C22—C21—H21 | 116.4 |
C1—C6—C5 | 119.46 (17) | C24i—C22—C23 | 118.45 (15) |
C1—C6—H6 | 120.3 | C24i—C22—C21 | 122.88 (16) |
C5—C6—H6 | 120.3 | C23—C22—C21 | 118.67 (15) |
C8—N7—C4 | 118.54 (16) | C24—C23—C22 | 121.39 (16) |
N7—C8—C10 | 122.57 (16) | C24—C23—H23 | 119.3 |
N7—C8—C9 | 117.80 (16) | C22—C23—H23 | 119.3 |
C10—C8—C9 | 119.64 (16) | C23—C24—C22i | 120.16 (16) |
C8—C9—H9A | 109.5 | C23—C24—H24 | 119.9 |
C8—C9—H9B | 109.5 | C22i—C24—H24 | 119.9 |
H9A—C9—H9B | 109.5 | C52—C51—H51A | 109.5 |
C8—C9—H9C | 109.5 | C52—C51—H51B | 109.5 |
H9A—C9—H9C | 109.5 | H51A—C51—H51B | 109.5 |
H9B—C9—H9C | 109.5 | C52—C51—H51C | 109.5 |
C11—C10—C8 | 120.02 (16) | H51A—C51—H51C | 109.5 |
C11—C10—C18 | 119.87 (16) | H51B—C51—H51C | 109.5 |
C8—C10—C18 | 120.11 (16) | O53—C52—C51 | 109.09 (18) |
C10—C11—C5 | 118.01 (16) | O53—C52—H52A | 109.9 |
C10—C11—C12 | 121.72 (16) | C51—C52—H52A | 109.9 |
C5—C11—C12 | 120.27 (16) | O53—C52—H52B | 109.9 |
C17—C12—C13 | 119.09 (17) | C51—C52—H52B | 109.9 |
C17—C12—C11 | 120.53 (16) | H52A—C52—H52B | 108.3 |
C13—C12—C11 | 120.37 (16) | O56—C54—O53 | 122.8 (2) |
C14—C13—C12 | 120.34 (17) | O56—C54—C55 | 126.9 (2) |
C14—C13—H13 | 119.8 | O53—C54—C55 | 110.3 (2) |
C12—C13—H13 | 119.8 | C54—C55—H55A | 109.5 |
C15—C14—C13 | 120.11 (18) | C54—C55—H55B | 109.5 |
C15—C14—H14 | 119.9 | H55A—C55—H55B | 109.5 |
C13—C14—H14 | 119.9 | C54—C55—H55C | 109.5 |
C14—C15—C16 | 119.97 (18) | H55A—C55—H55C | 109.5 |
C14—C15—H15 | 120 | H55B—C55—H55C | 109.5 |
C6—C1—C2—C3 | 1.2 (3) | C6—C5—C11—C12 | −1.6 (2) |
Cl1—C1—C2—C3 | −178.76 (14) | C10—C11—C12—C17 | 103.4 (2) |
C1—C2—C3—C4 | 0.2 (3) | C5—C11—C12—C17 | −77.3 (2) |
C2—C3—C4—N7 | 177.88 (17) | C10—C11—C12—C13 | −77.7 (2) |
C2—C3—C4—C5 | −1.6 (3) | C5—C11—C12—C13 | 101.7 (2) |
N7—C4—C5—C6 | −177.88 (16) | C17—C12—C13—C14 | −0.2 (3) |
C3—C4—C5—C6 | 1.5 (2) | C11—C12—C13—C14 | −179.20 (17) |
N7—C4—C5—C11 | 1.4 (3) | C12—C13—C14—C15 | −0.8 (3) |
C3—C4—C5—C11 | −179.16 (16) | C13—C14—C15—C16 | 0.8 (3) |
C2—C1—C6—C5 | −1.2 (3) | C14—C15—C16—C17 | 0.3 (3) |
Cl1—C1—C6—C5 | 178.76 (13) | C15—C16—C17—C12 | −1.3 (3) |
C4—C5—C6—C1 | −0.2 (3) | C13—C12—C17—C16 | 1.3 (3) |
C11—C5—C6—C1 | −179.47 (16) | C11—C12—C17—C16 | −179.74 (17) |
C5—C4—N7—C8 | −0.2 (3) | C11—C10—C18—O19 | 92.4 (2) |
C3—C4—N7—C8 | −179.66 (16) | C8—C10—C18—O19 | −87.7 (2) |
C4—N7—C8—C10 | −0.8 (3) | C11—C10—C18—C20 | −88.2 (2) |
C4—N7—C8—C9 | 179.53 (16) | C8—C10—C18—C20 | 91.7 (2) |
N7—C8—C10—C11 | 0.7 (3) | O19—C18—C20—C21 | 172.69 (18) |
C9—C8—C10—C11 | −179.70 (16) | C10—C18—C20—C21 | −6.7 (3) |
N7—C8—C10—C18 | −179.25 (16) | C18—C20—C21—C22 | −178.00 (16) |
C9—C8—C10—C18 | 0.4 (2) | C20—C21—C22—C24i | −3.7 (3) |
C8—C10—C11—C5 | 0.6 (2) | C20—C21—C22—C23 | 177.15 (17) |
C18—C10—C11—C5 | −179.55 (14) | C24i—C22—C23—C24 | −0.2 (3) |
C8—C10—C11—C12 | 179.94 (15) | C21—C22—C23—C24 | 179.00 (16) |
C18—C10—C11—C12 | −0.2 (2) | C22—C23—C24—C22i | 0.2 (3) |
C4—C5—C11—C10 | −1.5 (2) | C54—O53—C52—C51 | −86.6 (2) |
C6—C5—C11—C10 | 177.76 (15) | C52—O53—C54—O56 | −3.7 (3) |
C4—C5—C11—C12 | 179.09 (15) | C52—O53—C54—C55 | 176.92 (18) |
Symmetry code: (i) −x+1, −y, −z. |
Cg1 is the centroid of the C12–C17 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O19ii | 0.95 | 2.54 | 3.218 (2) | 128 |
C23—H23···O53 | 0.95 | 2.57 | 3.468 (2) | 157 |
C24—H24···O56iii | 0.95 | 2.48 | 3.410 (3) | 165 |
C51—H51B···Cg1iv | 0.98 | 2.76 | 3.627 (3) | 147 |
Symmetry codes: (ii) −x, −y, −z+1; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C44H30Cl2N2O2·2C4H8O2 |
Mr | 865.81 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 9.9851 (3), 10.0086 (2), 11.3676 (3) |
α, β, γ (°) | 102.350 (1), 97.108 (1), 95.290 (2) |
V (Å3) | 1092.94 (5) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.25 × 0.15 × 0.1 |
Data collection | |
Diffractometer | Bruker APEXII |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2002) |
Tmin, Tmax | 0.884, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18119, 4866, 4035 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.140, 1.04 |
No. of reflections | 4866 |
No. of parameters | 283 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.02, −0.42 |
Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2001), SIR2002 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 2012).
Cg1 is the centroid of the C12–C17 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O19i | 0.95 | 2.54 | 3.218 (2) | 128 |
C23—H23···O53 | 0.95 | 2.57 | 3.468 (2) | 157 |
C24—H24···O56ii | 0.95 | 2.48 | 3.410 (3) | 165 |
C51—H51B···Cg1iii | 0.98 | 2.76 | 3.627 (3) | 147 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) −x+1, −y+1, −z+1. |
Footnotes
‡Département Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Larbi Ben M'hidi, 04000 Oum El Bouaghi, Algeria.
Acknowledgements
We are grateful to all personnel of the research squad "Synthèse de molécules à objectif thérapeutique" of the PHYSYNOR Laboratory, Université Mentouri-Constantine, Algeria, for their assistance. Thanks are also due to the MESRS (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique - Algérie) for financial support.
References
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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.
In continuation of our interest related to the synthesis and structures of potentially bioactive products (Kedjadja et al. 2004; Menasra et al. 2005), we report herein the synthesis and the structure determination of the title compound, (I). The reactivity of this compound and its analogues toward nucleophiles is under investigation.
The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. The asymmetric unit of (I)consists of one-half of the molecule, with the other half generated by a crystallographic inversion centre. In the title molecule the centrosymmetric phenyl ring is attached to two prop-2-en-1-one linked to two 6-chloro-2-methyl-4-phenylquinolin-3-yl and two molecules of ethyl acetate are co-crystalized with it. The two rings of quinolyl group are fused in axial fashion and form adihedral angle of 1.72 (5)° and this quasi plane system forms a dihedral angle of 78.80 (6)° with the phenyl ring (C12—C17) attached to quinolyl moiety. The crystal packing can be described as layers in zigzag parallel to the (110) plane. (Fig. 2). It features C—H···O and C—H···π interactions (Table. 1) and strong π-π stacking interactions between quinolyl rings with a centroid-centroid distance of 3.7025 (11) and 3.8124 (10)å. These interactions link the molecules within the layers and also link the layers together, reinforcing the cohesion of the structure.