(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

Kedjadja, A.; Merdes, R.; Bouacida, S.; Roisnel, T.; Belfaitah, A.

doi:10.1107/S1600536812049422

organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Pages o37-o38

https://doi.org/10.1107/S1600536812049422

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(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

Allaoua Kedjadja,^a Rachid Merdes,^a Sofiane Bouacida,^b ^*‡ Thierry Roisnel ^c and Ali Belfaitah ^d

^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

(Received 28 November 2012; accepted 2 December 2012; online 8 December 2012)

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

C₄₄H₃₀Cl₂N₂O₂·2C₄H₈O₂
M_r = 865.81
Triclinic, $[P \overline 1]$
a = 9.9851 (3) Å
b = 10.0086 (2) Å
c = 11.3676 (3) Å
α = 102.350 (1)°
β = 97.108 (1)°
γ = 95.290 (2)°
V = 1092.94 (5) Å³
Z = 1
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 150 K
0.25 × 0.15 × 0.1 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ) T_min = 0.884, T_max = 0.980
18119 measured reflections
4866 independent reflections
4035 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.140
S = 1.04
4866 reflections
283 parameters
H-atom parameters constrained
Δρ_max = 1.02 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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.

Data collection: APEX2 (Bruker, 2001 ); cell refinement: 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

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812049422/hb7004sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049422/hb7004Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: 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).

Figures top

	Fig. 1. The molecular geometry of (I) with displacement ellipsoids drawn at the 50% probability level. Only the contents of the asymmetric unit are numbered. The two ethyl acetate co-crystalized molecules were omitted for clarity.
	Fig. 2. A diagram of the layered crystal packing of (I) viewed down the c axis.

(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 top

Crystal data top

C₄₄H₃₀Cl₂N₂O₂·2C₄H₈O₂	Z = 1
M_r = 865.81	F(000) = 454
Triclinic, P1	D_x = 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

Data collection top

Bruker APEXII diffractometer	4035 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
CCD rotation images, thin slices scans	θ_max = 27.5°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −12→12
T_min = 0.884, T_max = 0.980	k = −12→12
18119 measured reflections	l = −14→14
4866 independent reflections

Refinement top

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(F_o²) + (0.0694P)² + 0.8188P] where P = (F_o² + 2F_c²)/3
4866 reflections	(Δ/σ)_max = 0.011
283 parameters	Δρ_max = 1.02 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₄₄H₃₀Cl₂N₂O₂·2C₄H₈O₂	γ = 95.290 (2)°
M_r = 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)°

Data collection top

Bruker APEXII diffractometer	4866 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	4035 reflections with I > 2σ(I)
T_min = 0.884, T_max = 0.980	R_int = 0.026
18119 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.04	Δρ_max = 1.02 e Å⁻³
4866 reflections	Δρ_min = −0.42 e Å⁻³
283 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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···Cg1^iv	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
M_r	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)
T_min, T_max	0.884, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	18119, 4866, 4035
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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

Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany. Google Scholar
Bruker (2001). APEX2, SAINT and SADABS. 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
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kedjadja, A., Moussaoui, F., Debache, A., Rhouati, S. & Belfaitah, A. (2004). J. Soc. Alger. Chim. 14, 225–233. CAS Google Scholar
Menasra, H., Kedjadja, A., Debache, A., Rhouati, S., Carboni, B. & Belfaitah, A. (2005). Synth. Commun. 35, 2779–2788. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, G.-W., Jia, C.-C. & Dong, Y.-W. (2006). Tetrahedron Lett. 47, 1059–1063. Web of Science CrossRef CAS Google Scholar

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Volume 69| Part 1| January 2013| Pages o37-o38

https://doi.org/10.1107/S1600536812049422

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

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