rac-2-(2-Chloro-6-methyl­quinolin-3-yl)-2,3-dihydro­quinolin-4(1H)-one

Bouraiou, A.; Bouacida, S.; Bertrand, C.; Roisnel, T.; Belfaitah, A.

doi:10.1107/S1600536812020831

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1701-o1702

doi:10.1107/S1600536812020831

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access

rac-2-(2-Chloro-6-methylquinolin-3-yl)-2,3-dihydroquinolin-4(1H)-one

Abdelmalek Bouraiou,^a Sofiane Bouacida,^b ^* Carboni Bertrand,^c Thierry Roisnel ^d and Ali Belfaitah ^a

^aLaboratoire des Produits Naturels d'Origine Végétale et de Synthèse Organique (PHYSYNOR), Université Mentouri-Constantine, 25000 Constantine, Algeria, ^bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Université Mentouri-Constantine, 25000 Algeria, ^cUMR 6226 CNRS Sciences Chimiques de Rennes, Université de Rennes I, France, and ^dCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 18 April 2012; accepted 8 May 2012; online 12 May 2012)

In the title compound, C₁₉H₁₅ClN₂O, the quinoline ring forms a dihedral angle of 43.24 (1)° with the benzene ring of the dihydroquinolinyl system. In the crystal, molecules are linked through a single weak C—H⋯O hydrogen bond, forming ribbons which extend along (100), giving alternating zigzag molecular layers which stack down the b-axis direction.

Related literature

For applications of similar structures see: Chandrasekhar et al. (2007 ); Varma & Saini (1997 ); Donnelly & Farrell (1990 ); Hemanth Kumar et al. (2004 ). For the synthesis of the 2-aminochalcone, see: Gao et al. (1996 ). For related structures, see: Bouraiou et al. (2008 , 2011 ); Belfaitah et al. (2006 ); Benzerka et al. (2011 ).

Experimental

Crystal data

C₁₉H₁₅ClN₂O
M_r = 322.78
Orthorhombic, P b c a
a = 13.8912 (8) Å
b = 12.4572 (4) Å
c = 17.8617 (11) Å
V = 3090.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 295 K
0.15 × 0.06 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer
6664 measured reflections
3537 independent reflections
1696 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.169
S = 1.00
3537 reflections
212 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O1ⁱ	0.93	2.49	3.243 (5)	138
Symmetry code: (i) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia,1997 ) and DIAMOND (Brandenburg & Berndt, 2001 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812020831/zs2200sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020831/zs2200Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812020831/zs2200Isup3.cml

checkCIF report

Comment top

2-Substituted dihydroquinolinones have important medicinal properties as new chemical entities and also serve as building blocks for creating further diversity in SAR studies in various therapeutic areas (Chandrasekhar et al., 2007). Convenient synthesis of 2-aminochalcone and its amide derivatives and the ready cyclization of these compounds to 2-aryl-2,3-dihydroquinolin-4(1H)-ones have been widely explored (Varma & Saini, 1997; Donnelly & Farrell, 1990). Silica gel supported InCl₃ (20 mol %) is a new solid-support catalyst that can be used under solvent-free conditions for the facile and efficient isomerization of 2-aminochalcones to the corresponding 2-aryl-2,3-dihydroquinolin-4(1H)-ones (Hemanth Kumar et al., 2004). As a part of a program directed toward the synthesis of new suitably functionalized heterocyclic compounds of potential biological activity (Bouraiou et al., 2008, 2011; Benzerka et al., 2011), we report herein the synthesis and structure determination of the title compound, C₁₉H₁₅ClN₂ O.

In the title compound (Fig. 1), the quinoline ring forms a dihedral angle of 43.24 (1)° with the phenyl ring of the 2,3-dihydroquinolin-4(1H)-one moiety. The geometric parameters are in agreement with those of other structures possessing a quinolyl substituent, previously reported in the literature (Belfaitah et al., 2006; Benzerka et al., 2011). The crystal structure can be described as alterning zigzag ribbons which stack down the b axis of the unit cell (Fig. 2), these ribbons comprising molecules linked through a single weak intermolecular C17—H···O1 hydrogen bond (Table 1), and extending down a (Fig. 3). The hetero N2—H2 group has no acceptor in the crystal structure.

Related literature top

For applications of similar structures see: Chandrasekhar et al. (2007); Varma & Saini (1997); Donnelly & Farrell (1990); Hemanth Kumar et al. (2004). For the synthesis of the 2-aminochalcone, see: Gao et al. (1996). For related structures, see: Bouraiou et al. (2008, 2011); Belfaitah et al. (2006); Benzerka et al. (2011).

Experimental top

2-Aminoacetophenone (1mmol) was first condensed with 2-chloro-3-formyl-6-methylquinoline (2 mmol) to give the corresponding 2-aminochalcone in 74% yield, according to the procedure described by Gao et al. (1996). In the next step, a mixture of 2-aminochalcone (100 mg) and 1 g of silica gel impregnated with indium(III) chloride (20 mol%, 13.6 mg) was irradiated in a domestic microwave oven at 360 W for 5 minutes. Under these conditions, the title compound was successfully synthesized in good yield (69%). Single crystals suitable for the X-ray diffraction analysis were obtained by dissolving the compound in a diisopropyl ether/CHCl₃ solvent mixture and allowing the solution to slowly evaporate at room temperature.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia,1997) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A diagram of the layered zigzag packing in the crystal viewed down the a axis.
	Fig. 3. A part of crystal packing viewed down the b axis showing hydrogen-bond interactions as dashed lines.

rac-2-(2-Chloro-6-methylquinolin-3-yl)-2,3- dihydroquinolin-4(1H)-one top

Crystal data top

C₁₉H₁₅ClN₂O	F(000) = 1344
M_r = 322.78	D_x = 1.387 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3949 reflections
a = 13.8912 (8) Å	θ = 2.9–27.5°
b = 12.4572 (4) Å	µ = 0.25 mm⁻¹
c = 17.8617 (11) Å	T = 295 K
V = 3090.9 (3) Å³	Needle, colourless
Z = 8	0.15 × 0.06 × 0.05 mm

Data collection top

Nonius KappaCCD diffractometer	1696 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590 diffractometer	R_int = 0.072
Graphite monochromator	θ_max = 27.5°, θ_min = 2.9°
Detector resolution: 9 pixels mm^-1	h = −18→17
CCD rotation images, thick slices scans	k = −16→16
6664 measured reflections	l = −23→23
3537 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0676P)² + 0.5198P] where P = (F_o² + 2F_c²)/3
3537 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₉H₁₅ClN₂O	V = 3090.9 (3) Å³
M_r = 322.78	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.8912 (8) Å	µ = 0.25 mm⁻¹
b = 12.4572 (4) Å	T = 295 K
c = 17.8617 (11) Å	0.15 × 0.06 × 0.05 mm

Data collection top

Nonius KappaCCD diffractometer	1696 reflections with I > 2σ(I)
6664 measured reflections	R_int = 0.072
3537 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.21 e Å⁻³
3537 reflections	Δρ_min = −0.27 e Å⁻³
212 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
Cl1	1.00123 (7)	0.53833 (7)	0.38618 (6)	0.0598 (3)
O1	1.00620 (19)	0.1322 (2)	0.36882 (17)	0.0724 (9)
N1	0.8795 (2)	0.6237 (2)	0.47797 (17)	0.0467 (7)
N2	0.7597 (2)	0.3073 (2)	0.34987 (16)	0.0461 (7)
C1	0.8911 (2)	0.5416 (2)	0.43385 (19)	0.0430 (8)
C2	0.8250 (2)	0.4560 (2)	0.42234 (18)	0.0408 (7)
C3	0.7405 (2)	0.4630 (2)	0.46099 (18)	0.0430 (8)
H3	0.6944	0.4096	0.4554	0.052*
C4	0.7221 (2)	0.5504 (2)	0.50953 (18)	0.0411 (8)
C5	0.6356 (2)	0.5626 (2)	0.54971 (19)	0.0453 (8)
H5	0.5879	0.5108	0.5447	0.054*
C6	0.6196 (3)	0.6486 (2)	0.59604 (19)	0.0474 (9)
C7	0.6938 (3)	0.7251 (3)	0.60359 (19)	0.0515 (9)
H7	0.6842	0.7834	0.6353	0.062*
C8	0.7791 (3)	0.7169 (2)	0.56608 (19)	0.0508 (9)
H8	0.8269	0.7682	0.5728	0.061*
C9	0.7940 (2)	0.6298 (2)	0.51708 (19)	0.0424 (8)
C10	0.5261 (3)	0.6631 (3)	0.6368 (2)	0.0687 (12)
H10A	0.4871	0.7146	0.6107	0.103*
H10B	0.5385	0.6883	0.6867	0.103*
H10C	0.4927	0.5957	0.6391	0.103*
C11	0.8477 (2)	0.3617 (2)	0.37226 (19)	0.0442 (8)
H11	0.8803	0.3883	0.3273	0.053*
C12	0.9131 (3)	0.2810 (2)	0.41094 (19)	0.0479 (9)
H12A	0.9741	0.3151	0.4226	0.058*
H12B	0.8838	0.2588	0.4577	0.058*
C13	0.9313 (3)	0.1834 (3)	0.3631 (2)	0.0475 (8)
C14	0.8524 (2)	0.1510 (2)	0.31357 (18)	0.0420 (8)
C15	0.7678 (2)	0.2110 (2)	0.31041 (18)	0.0412 (8)
C16	0.6899 (3)	0.1735 (3)	0.2677 (2)	0.0523 (9)
H16	0.633	0.2127	0.266	0.063*
C17	0.6976 (3)	0.0793 (3)	0.2284 (2)	0.0534 (9)
H17	0.6453	0.0546	0.2008	0.064*
C18	0.7825 (3)	0.0204 (3)	0.2292 (2)	0.0559 (9)
H18	0.7878	−0.0423	0.2012	0.067*
C19	0.8584 (3)	0.0556 (2)	0.2717 (2)	0.0505 (9)
H19	0.915	0.0157	0.2728	0.061*
H2	0.717 (3)	0.348 (2)	0.3321 (19)	0.05*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0485 (5)	0.0545 (5)	0.0763 (7)	−0.0051 (4)	0.0144 (5)	0.0027 (5)
O1	0.0539 (18)	0.0643 (16)	0.099 (2)	0.0201 (13)	−0.0134 (16)	−0.0173 (15)
N1	0.0479 (18)	0.0388 (14)	0.0534 (17)	−0.0029 (13)	−0.0024 (14)	−0.0010 (13)
N2	0.0408 (17)	0.0419 (15)	0.0554 (18)	0.0075 (12)	−0.0080 (14)	−0.0077 (13)
C1	0.0382 (19)	0.0412 (17)	0.050 (2)	0.0007 (14)	0.0014 (15)	0.0067 (15)
C2	0.0450 (19)	0.0353 (16)	0.0421 (18)	0.0008 (14)	−0.0046 (16)	0.0041 (14)
C3	0.045 (2)	0.0360 (16)	0.0482 (19)	−0.0027 (14)	−0.0011 (16)	−0.0015 (15)
C4	0.047 (2)	0.0352 (15)	0.0412 (18)	0.0007 (15)	0.0025 (15)	0.0043 (14)
C5	0.047 (2)	0.0378 (16)	0.051 (2)	−0.0021 (14)	−0.0016 (17)	0.0033 (15)
C6	0.057 (2)	0.0407 (17)	0.045 (2)	0.0054 (16)	0.0057 (17)	0.0048 (15)
C7	0.062 (2)	0.0438 (18)	0.049 (2)	0.0108 (17)	−0.0084 (19)	−0.0058 (16)
C8	0.059 (2)	0.0394 (17)	0.053 (2)	−0.0029 (16)	−0.0091 (19)	−0.0063 (16)
C9	0.043 (2)	0.0382 (16)	0.0454 (19)	−0.0004 (14)	−0.0040 (16)	0.0028 (14)
C10	0.075 (3)	0.054 (2)	0.078 (3)	0.007 (2)	0.022 (2)	−0.004 (2)
C11	0.042 (2)	0.0401 (17)	0.050 (2)	0.0005 (14)	−0.0020 (16)	−0.0038 (15)
C12	0.047 (2)	0.0439 (18)	0.053 (2)	0.0052 (15)	−0.0083 (17)	−0.0013 (15)
C13	0.042 (2)	0.0461 (18)	0.054 (2)	0.0036 (16)	0.0013 (17)	0.0044 (16)
C14	0.044 (2)	0.0397 (16)	0.0423 (19)	−0.0002 (14)	0.0043 (15)	0.0014 (14)
C15	0.042 (2)	0.0396 (16)	0.0419 (18)	0.0000 (14)	0.0038 (15)	0.0004 (14)
C16	0.047 (2)	0.055 (2)	0.055 (2)	−0.0028 (16)	−0.0017 (17)	−0.0058 (17)
C17	0.060 (3)	0.053 (2)	0.047 (2)	−0.0127 (17)	−0.0048 (19)	−0.0062 (16)
C18	0.071 (3)	0.0454 (18)	0.051 (2)	−0.0023 (18)	0.005 (2)	−0.0066 (16)
C19	0.061 (2)	0.0423 (17)	0.048 (2)	0.0054 (16)	0.0067 (19)	0.0001 (16)

Geometric parameters (Å, º) top

Cl1—C1	1.751 (3)	C8—H8	0.93
O1—C13	1.224 (4)	C10—H10A	0.96
N1—C1	1.301 (4)	C10—H10B	0.96
N1—C9	1.380 (4)	C10—H10C	0.96
N2—C15	1.395 (4)	C11—C12	1.522 (4)
N2—C11	1.454 (4)	C11—H11	0.98
N2—H2	0.85 (3)	C12—C13	1.507 (4)
C1—C2	1.423 (4)	C12—H12A	0.97
C2—C3	1.364 (5)	C12—H12B	0.97
C2—C11	1.509 (4)	C13—C14	1.466 (5)
C3—C4	1.415 (4)	C14—C15	1.395 (4)
C3—H3	0.93	C14—C19	1.406 (4)
C4—C5	1.407 (5)	C15—C16	1.404 (4)
C4—C9	1.412 (4)	C16—C17	1.372 (4)
C5—C6	1.372 (4)	C16—H16	0.93
C5—H5	0.93	C17—C18	1.389 (5)
C6—C7	1.410 (5)	C17—H17	0.93
C6—C10	1.500 (5)	C18—C19	1.372 (5)
C7—C8	1.365 (5)	C18—H18	0.93
C7—H7	0.93	C19—H19	0.93
C8—C9	1.409 (4)

C1—N1—C9	117.2 (3)	H10A—C10—H10C	109.5
C15—N2—C11	118.2 (3)	H10B—C10—H10C	109.5
C15—N2—H2	112 (2)	N2—C11—C2	110.5 (3)
C11—N2—H2	115 (2)	N2—C11—C12	108.6 (3)
N1—C1—C2	126.6 (3)	C2—C11—C12	111.7 (3)
N1—C1—Cl1	114.9 (2)	N2—C11—H11	108.7
C2—C1—Cl1	118.4 (2)	C2—C11—H11	108.7
C3—C2—C1	115.7 (3)	C12—C11—H11	108.7
C3—C2—C11	122.0 (3)	C13—C12—C11	112.1 (3)
C1—C2—C11	122.3 (3)	C13—C12—H12A	109.2
C2—C3—C4	121.1 (3)	C11—C12—H12A	109.2
C2—C3—H3	119.5	C13—C12—H12B	109.2
C4—C3—H3	119.5	C11—C12—H12B	109.2
C5—C4—C9	118.7 (3)	H12A—C12—H12B	107.9
C5—C4—C3	123.4 (3)	O1—C13—C14	122.8 (3)
C9—C4—C3	118.0 (3)	O1—C13—C12	121.0 (3)
C6—C5—C4	122.0 (3)	C14—C13—C12	116.1 (3)
C6—C5—H5	119	C15—C14—C19	118.8 (3)
C4—C5—H5	119	C15—C14—C13	120.5 (3)
C5—C6—C7	117.9 (3)	C19—C14—C13	120.6 (3)
C5—C6—C10	121.8 (3)	C14—C15—N2	120.5 (3)
C7—C6—C10	120.3 (3)	C14—C15—C16	119.5 (3)
C8—C7—C6	122.4 (3)	N2—C15—C16	119.9 (3)
C8—C7—H7	118.8	C17—C16—C15	120.2 (3)
C6—C7—H7	118.8	C17—C16—H16	119.9
C7—C8—C9	119.4 (3)	C15—C16—H16	119.9
C7—C8—H8	120.3	C16—C17—C18	120.9 (3)
C9—C8—H8	120.3	C16—C17—H17	119.6
N1—C9—C8	118.9 (3)	C18—C17—H17	119.6
N1—C9—C4	121.5 (3)	C19—C18—C17	119.3 (3)
C8—C9—C4	119.6 (3)	C19—C18—H18	120.4
C6—C10—H10A	109.5	C17—C18—H18	120.4
C6—C10—H10B	109.5	C18—C19—C14	121.3 (3)
H10A—C10—H10B	109.5	C18—C19—H19	119.4
C6—C10—H10C	109.5	C14—C19—H19	119.4

C9—N1—C1—C2	−1.0 (5)	C15—N2—C11—C12	−50.0 (4)
C9—N1—C1—Cl1	−179.8 (2)	C3—C2—C11—N2	21.5 (4)
N1—C1—C2—C3	1.2 (5)	C1—C2—C11—N2	−160.2 (3)
Cl1—C1—C2—C3	180.0 (2)	C3—C2—C11—C12	−99.5 (4)
N1—C1—C2—C11	−177.2 (3)	C1—C2—C11—C12	78.8 (4)
Cl1—C1—C2—C11	1.6 (4)	N2—C11—C12—C13	54.4 (4)
C1—C2—C3—C4	−0.5 (5)	C2—C11—C12—C13	176.5 (3)
C11—C2—C3—C4	177.9 (3)	C11—C12—C13—O1	151.2 (3)
C2—C3—C4—C5	178.9 (3)	C11—C12—C13—C14	−32.2 (4)
C2—C3—C4—C9	−0.4 (5)	O1—C13—C14—C15	178.7 (3)
C9—C4—C5—C6	−0.4 (5)	C12—C13—C14—C15	2.1 (5)
C3—C4—C5—C6	−179.6 (3)	O1—C13—C14—C19	2.3 (5)
C4—C5—C6—C7	−1.0 (5)	C12—C13—C14—C19	−174.2 (3)
C4—C5—C6—C10	177.9 (3)	C19—C14—C15—N2	−178.6 (3)
C5—C6—C7—C8	0.8 (5)	C13—C14—C15—N2	5.0 (5)
C10—C6—C7—C8	−178.2 (3)	C19—C14—C15—C16	2.0 (5)
C6—C7—C8—C9	0.9 (5)	C13—C14—C15—C16	−174.4 (3)
C1—N1—C9—C8	179.3 (3)	C11—N2—C15—C14	20.8 (4)
C1—N1—C9—C4	0.0 (5)	C11—N2—C15—C16	−159.8 (3)
C7—C8—C9—N1	178.4 (3)	C14—C15—C16—C17	−1.0 (5)
C7—C8—C9—C4	−2.3 (5)	N2—C15—C16—C17	179.6 (3)
C5—C4—C9—N1	−178.6 (3)	C15—C16—C17—C18	−1.0 (5)
C3—C4—C9—N1	0.7 (5)	C16—C17—C18—C19	1.9 (6)
C5—C4—C9—C8	2.0 (5)	C17—C18—C19—C14	−0.9 (5)
C3—C4—C9—C8	−178.7 (3)	C15—C14—C19—C18	−1.0 (5)
C15—N2—C11—C2	−172.8 (3)	C13—C14—C19—C18	175.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N2	0.93	2.45	2.788 (4)	102
C11—H11···Cl1	0.98	2.72	3.074 (3)	102
C17—H17···O1ⁱ	0.93	2.49	3.243 (5)	138

Symmetry code: (i) x−1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅ClN₂O
M_r	322.78
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	13.8912 (8), 12.4572 (4), 17.8617 (11)
V (Å³)	3090.9 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.15 × 0.06 × 0.05

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6664, 3537, 1696
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.169, 1.00
No. of reflections	3537
No. of parameters	212
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.27

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia,1997) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O1ⁱ	0.93	2.49	3.243 (5)	138

Symmetry code: (i) x−1/2, y, −z+1/2.

Acknowledgements

We are grateful to all personal of PHYSYNOR laboratory, Université Mentouri-Constantine, Algeria, for their assistance. Thanks are due to MESRS and ANDRU (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique et l'Agence Nationale pour le Développement de la Recherche Universitaire) (Algeria) via the PNR programm for financial support.

References

Belfaitah, A., Ladraa, S., Bouraiou, A., Benali-Cherif, N., Debache, A. & Rhouati, S. (2006). Acta Cryst. E62, o1355–o1357. Web of Science CSD CrossRef IUCr Journals Google Scholar
Benzerka, S., Bouraiou, A., Bouacida, S., Roisnel, T. & Belfaitah, A. (2011). Acta Cryst. E67, o2084–o2085. Web of Science 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 GbR, Bonn, Germany. Google Scholar
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103. CrossRef IUCr Journals Google Scholar
Chandrasekhar, S., Vijeender, K. & Sridhar, C. (2007). Tetrahedron Lett. 48, 4935–4937. Web of Science CrossRef CAS Google Scholar
Donnelly, J. A. & Farrell, D. F. (1990). J. Org. Chem. 55, 1757–1761. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gao, F., Johnson, K. F. & Schlenoff, J. B. (1996). J. Chem. Soc. Perkin Trans. 2, pp. 269–273. CrossRef Google Scholar
Hemanth Kumar, K., Muralidharan, D. & Perumal, P. T. (2004). Synthesis, 1, 63–69. Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Varma, R. S. & Saini, R. K. (1997). Synlett, pp. 857–858. CrossRef Google Scholar