2-(2-Chloro-6,7-dimethyl­quinolin-3-yl)-2,3-dihydro­quinolin-4(1H)-one

Benzerka, S.; Bouraiou, A.; Bouacida, S.; Roisnel, T.; Belfaitah, A.

doi:10.1107/S1600536811028170

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages o2084-o2085

doi:10.1107/S1600536811028170

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2-(2-Chloro-6,7-dimethylquinolin-3-yl)-2,3-dihydroquinolin-4(1H)-one

Saida Benzerka,^a Abdelmalek Bouraiou,^b Sofiane Bouacida,^b ^* Thierry Roisnel ^c 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, and ^cCentre 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 9 July 2011; accepted 13 July 2011; online 23 July 2011)

In the title molecule, C₂₀H₁₇ClN₂O, the dihedral angle between the mean plane of the quinoline ring system and the benzene ring of the dihydroquinolinone moiety is 57.84 (8)°. In the crystal, molecules are linked into centrosymmetric dimers via pairs of intermolecular N—H⋯N hydrogen bonds. These dimers are further stabilized by weak π–π stacking interactions between pyridine rings with a centroid–centroid distance of 3.9414 (12) Å.

Related literature

For quinoline compounds and their applications, see: Prakash et al. (1994 ); Singh & Kapil (1993 ); Kalinin et al. (1992 ); Xia et al. (1992 ); Donnelly & Farrell (1990a ,b ); Kumar et al. (2004 ); Varma & Saini (1997 ); Tokes & Litkei (1993 ); Tokes & Szilagyi (1987 ); Tokes et al. (1992 ). For our previous work on quinoline derivatives, see: Belfaitah et al. (2006 ); Bouraiou et al. (2008 , 2010 , 2011 ); Benzerka et al. (2010 ); Ladraa et al. (2010 ).

Experimental

Crystal data

C₂₀H₁₇ClN₂O
M_r = 336.81
Triclinic, $[P \overline 1]$
a = 7.7345 (4) Å
b = 10.6196 (6) Å
c = 11.3463 (4) Å
α = 96.425 (2)°
β = 100.068 (3)°
γ = 109.576 (1)°
V = 849.84 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 295 K
0.15 × 0.06 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer
7058 measured reflections
3863 independent reflections
2507 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.133
S = 1.00
3863 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯N1ⁱ	0.86 (2)	2.53 (2)	3.297 (2)	148.6 (18)
Symmetry code: (i) -x, -y, -z+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., 2005 ); 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 datablock global. DOI: 10.1107/S1600536811028170/lh5284sup1.cif

Supporting information file. DOI: 10.1107/S1600536811028170/lh5284globalsup2.cml

checkCIF report

Comment top

2-Phenyl-2,3-dihydroquinolin-4(1H)-one compound substituted on the aromatic rings are valuable precursors (Prakash et al., 1994; Singh & Kapil, 1993) for the synthesis of medicinally important compounds, which are often not readily accessible by other means (Kalinin et al., 1992; Xia et al., 1992). 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 the procedures involve the use of corrosive reagents such as orthophosphoric acid, acetic acid or strong alkali. Many attempts have been made to explore efficient catalysts to accelerate this kind of reaction. Some of them are of limited synthetic scope due to low yields, long reaction times and the need for large amount of catalyst, specialized solvents or microwave activation (Tokes & Szilagyi, 1987; Tokes et al., 1992; Kumar et al. 2004; Varma & Saini, 1997). In continuation of our studies on quinoline derivatives and their biological activities (Bouraiou et al., 2010; Benzerka et al., 2010; Ladraa et al., 2010) we report herein the synthesis and structure determination of 2-(2-chloro-6,7-dimethylquinolin-3-yl)-2,3-dihydroquinolin-4(1H)-one I (Bouraiou et al., 2011). Characterization of the compound I was made from its spectral data (¹H-NMR, ¹³C-NMR), and was unequivocally established from an X-ray crystallographic determination (I).

The molecular structure of (I) is shown in Fig. 1. The two rings of quinolyl moiety are fused in an axial fashion and form a dihedral angle of 0.28 (7)° and this quasi plane system forms dihedral angles of 57.84 (8)° with the benzene ring (C15-C20). The geometric parameters of (I) are in agreement with those of other structures possessing a quinolyl substituent previously reported in the literature (Belfaitah et al., 2006; Bouraiou et al., 2008; Bouraiou et al., 2011). In the crystal, molecules are linked into centrosymmetric dimers via pairs of intermolecular N–H···N hydrogen bonds (Fig. 2). These dimers are further stabilized by π–π stacking interactions between pyridine rings with a centroid to centroid distance of 3.9414 (12)Å.

Related literature top

For quinoline compounds and their applications, see: Prakash et al. (1994); Singh & Kapil (1993); Kalinin et al. (1992); Xia et al. (1992); Donnelly & Farrell (1990a,b); Kumar et al. (2004); Varma & Saini (1997); Tokes & Litkei (1993); Tokes & Szilagyi (1987); Tokes et al. (1992). For our previous work on quinoline derivatives, see: Belfaitah et al. (2006); Bouraiou et al. (2008, 2010, 2011); Benzerka et al. (2010); Ladraa et al. (2010).

Experimental top

A mixture of (E)-1-(2-aminophenyl)-3-(2-chloro-6,7-dimethylquinolin-3-yl)prop-2-en-1-one and silica gel (1 g) impregnated with indium (III) chloride (20 mol%) was irradiated in domestic microwave oven at 360 W for 5 minutes (Bouraiou et al., 2011). Under these conditions, compound (I) was successfully synthesized in good yield (63%). A suitable crystal of title compound were obtained by crystallization from a CH₂Cl₂/di-isopropylether solution.

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., 2005); 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 molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Part of the crytal structure viewed along the b axis showing hydrogen bonds as dashed lines.

2-(2-Chloro-6,7-dimethylquinolin-3-yl)-2,3-dihydroquinolin-4(1H)-one top

Crystal data top

C₂₀H₁₇ClN₂O	Z = 2
M_r = 336.81	F(000) = 352
Triclinic, P1	D_x = 1.316 Mg m⁻³
a = 7.7345 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6196 (6) Å	Cell parameters from 3734 reflections
c = 11.3463 (4) Å	θ = 2.9–27.5°
α = 96.425 (2)°	µ = 0.23 mm⁻¹
β = 100.068 (3)°	T = 295 K
γ = 109.576 (1)°	Needle, white
V = 849.84 (7) Å³	0.15 × 0.06 × 0.05 mm

Data collection top

Nonius KappaCCD diffractometer	2507 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	R_int = 0.029
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
Detector resolution: 9 pixels mm^-1	h = −10→10
CCD rotation images, thick slices scans	k = −13→13
7058 measured reflections	l = −14→14
3863 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) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0621P)² + 0.0886P] where P = (F_o² + 2F_c²)/3
3863 reflections	(Δ/σ)_max < 0.001
222 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₀H₁₇ClN₂O	γ = 109.576 (1)°
M_r = 336.81	V = 849.84 (7) Å³
Triclinic, P1	Z = 2
a = 7.7345 (4) Å	Mo Kα radiation
b = 10.6196 (6) Å	µ = 0.23 mm⁻¹
c = 11.3463 (4) Å	T = 295 K
α = 96.425 (2)°	0.15 × 0.06 × 0.05 mm
β = 100.068 (3)°

Data collection top

Nonius KappaCCD diffractometer	2507 reflections with I > 2σ(I)
7058 measured reflections	R_int = 0.029
3863 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.17 e Å⁻³
3863 reflections	Δρ_min = −0.20 e Å⁻³
222 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
C1	0.2476 (3)	−0.00341 (19)	0.99805 (16)	0.0463 (4)
C2	0.2561 (2)	0.13287 (18)	1.01932 (15)	0.0442 (4)
C3	0.2601 (3)	0.18540 (19)	1.13579 (16)	0.0474 (4)
H3	0.2659	0.2744	1.1546	0.057*
C4	0.2556 (3)	0.10607 (19)	1.22794 (16)	0.0475 (4)
C5	0.2595 (3)	0.1535 (2)	1.35012 (17)	0.0549 (5)
H5	0.2666	0.2423	1.3728	0.066*
C6	0.2531 (3)	0.0720 (2)	1.43636 (17)	0.0578 (5)
C7	0.2407 (3)	−0.0639 (2)	1.40197 (18)	0.0579 (5)
C8	0.2379 (3)	−0.1118 (2)	1.28402 (18)	0.0558 (5)
H8	0.2314	−0.2007	1.2624	0.067*
C9	0.2446 (2)	−0.02881 (19)	1.19481 (16)	0.0476 (4)
C10	0.2307 (4)	−0.1569 (3)	1.4943 (2)	0.0806 (7)
H10A	0.2206	−0.2449	1.4553	0.121*
H10B	0.1225	−0.1653	1.5278	0.121*
H10C	0.3427	−0.1194	1.5584	0.121*
C11	0.2620 (4)	0.1278 (3)	1.56687 (18)	0.0767 (7)
H11A	0.3749	0.1284	1.6184	0.115*
H11B	0.1542	0.0716	1.5921	0.115*
H11C	0.2625	0.2188	1.5729	0.115*
C12	0.2648 (2)	0.21733 (18)	0.91943 (16)	0.0448 (4)
H12	0.1964	0.1569	0.8412	0.054*
C13	0.4673 (3)	0.2922 (2)	0.91241 (18)	0.0535 (5)
H13A	0.5382	0.3471	0.9914	0.064*
H13B	0.5245	0.2265	0.8924	0.064*
C14	0.4785 (3)	0.3822 (2)	0.81848 (18)	0.0566 (5)
C15	0.3261 (3)	0.43479 (19)	0.79376 (17)	0.0524 (5)
C16	0.3250 (4)	0.5217 (2)	0.7094 (2)	0.0738 (7)
H16	0.4184	0.5419	0.6653	0.089*
C17	0.1893 (4)	0.5769 (3)	0.6911 (3)	0.0911 (9)
H17	0.1905	0.6342	0.6348	0.109*
C18	0.0495 (4)	0.5478 (3)	0.7563 (3)	0.0833 (8)
H18	−0.0425	0.5862	0.7438	0.1*
C19	0.0459 (3)	0.4632 (2)	0.8389 (2)	0.0609 (5)
H19	−0.0483	0.4446	0.8824	0.073*
C20	0.1829 (3)	0.40416 (18)	0.85847 (16)	0.0480 (4)
N1	0.2392 (2)	−0.08277 (15)	1.07803 (14)	0.0498 (4)
N2	0.1772 (2)	0.31720 (17)	0.94168 (14)	0.0488 (4)
H2N	0.066 (3)	0.284 (2)	0.9549 (18)	0.059*
O1	0.6107 (2)	0.4116 (2)	0.76829 (17)	0.0858 (5)
Cl1	0.24838 (8)	−0.07686 (5)	0.85241 (5)	0.06466 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0434 (10)	0.0469 (10)	0.0467 (9)	0.0148 (8)	0.0099 (7)	0.0071 (7)
C2	0.0408 (9)	0.0471 (10)	0.0440 (9)	0.0149 (8)	0.0086 (7)	0.0108 (7)
C3	0.0513 (11)	0.0436 (10)	0.0484 (9)	0.0177 (8)	0.0121 (8)	0.0101 (8)
C4	0.0465 (10)	0.0507 (11)	0.0448 (9)	0.0160 (8)	0.0106 (8)	0.0115 (8)
C5	0.0545 (12)	0.0603 (12)	0.0492 (10)	0.0194 (10)	0.0121 (9)	0.0114 (9)
C6	0.0499 (11)	0.0743 (14)	0.0460 (10)	0.0165 (10)	0.0108 (8)	0.0172 (9)
C7	0.0469 (11)	0.0706 (14)	0.0560 (11)	0.0163 (10)	0.0106 (9)	0.0281 (10)
C8	0.0523 (11)	0.0522 (12)	0.0602 (12)	0.0141 (9)	0.0088 (9)	0.0210 (9)
C9	0.0416 (10)	0.0491 (11)	0.0497 (10)	0.0124 (8)	0.0087 (8)	0.0150 (8)
C10	0.0827 (17)	0.0918 (19)	0.0721 (14)	0.0277 (14)	0.0192 (12)	0.0446 (13)
C11	0.0823 (17)	0.0991 (19)	0.0475 (11)	0.0304 (15)	0.0157 (11)	0.0156 (12)
C12	0.0453 (10)	0.0455 (10)	0.0436 (9)	0.0153 (8)	0.0107 (7)	0.0113 (7)
C13	0.0458 (10)	0.0588 (12)	0.0592 (11)	0.0198 (9)	0.0144 (9)	0.0170 (9)
C14	0.0492 (11)	0.0569 (12)	0.0599 (11)	0.0110 (9)	0.0169 (9)	0.0144 (9)
C15	0.0515 (11)	0.0424 (10)	0.0562 (11)	0.0070 (9)	0.0107 (9)	0.0144 (8)
C16	0.0760 (16)	0.0627 (14)	0.0876 (16)	0.0178 (12)	0.0308 (13)	0.0370 (12)
C17	0.102 (2)	0.0756 (18)	0.114 (2)	0.0372 (16)	0.0319 (17)	0.0595 (16)
C18	0.0805 (17)	0.0698 (16)	0.115 (2)	0.0385 (14)	0.0229 (15)	0.0436 (15)
C19	0.0586 (12)	0.0517 (12)	0.0761 (13)	0.0229 (10)	0.0156 (10)	0.0171 (10)
C20	0.0470 (10)	0.0381 (9)	0.0519 (10)	0.0095 (8)	0.0060 (8)	0.0073 (8)
N1	0.0514 (9)	0.0441 (9)	0.0530 (8)	0.0159 (7)	0.0107 (7)	0.0121 (7)
N2	0.0466 (9)	0.0510 (9)	0.0541 (9)	0.0193 (7)	0.0164 (7)	0.0177 (7)
O1	0.0641 (10)	0.1091 (14)	0.0992 (12)	0.0288 (10)	0.0431 (9)	0.0487 (11)
Cl1	0.0817 (4)	0.0589 (3)	0.0535 (3)	0.0264 (3)	0.0186 (2)	0.0028 (2)

Geometric parameters (Å, º) top

C1—N1	1.301 (2)	C11—H11B	0.96
C1—C2	1.418 (3)	C11—H11C	0.96
C1—Cl1	1.7485 (19)	C12—N2	1.459 (2)
C2—C3	1.367 (2)	C12—C13	1.521 (3)
C2—C12	1.519 (2)	C12—H12	0.98
C3—C4	1.412 (2)	C13—C14	1.504 (3)
C3—H3	0.93	C13—H13A	0.97
C4—C9	1.410 (3)	C13—H13B	0.97
C4—C5	1.413 (3)	C14—O1	1.223 (2)
C5—C6	1.373 (3)	C14—C15	1.463 (3)
C5—H5	0.93	C15—C20	1.403 (3)
C6—C7	1.420 (3)	C15—C16	1.403 (3)
C6—C11	1.513 (3)	C16—C17	1.360 (4)
C7—C8	1.371 (3)	C16—H16	0.93
C7—C10	1.512 (3)	C17—C18	1.385 (4)
C8—C9	1.411 (2)	C17—H17	0.93
C8—H8	0.93	C18—C19	1.367 (3)
C9—N1	1.371 (2)	C18—H18	0.93
C10—H10A	0.96	C19—C20	1.400 (3)
C10—H10B	0.96	C19—H19	0.93
C10—H10C	0.96	C20—N2	1.389 (2)
C11—H11A	0.96	N2—H2N	0.86 (2)

N1—C1—C2	126.09 (17)	H11B—C11—H11C	109.5
N1—C1—Cl1	114.81 (14)	N2—C12—C2	110.34 (14)
C2—C1—Cl1	119.11 (13)	N2—C12—C13	108.54 (15)
C3—C2—C1	116.21 (16)	C2—C12—C13	111.35 (15)
C3—C2—C12	121.63 (17)	N2—C12—H12	108.9
C1—C2—C12	122.15 (16)	C2—C12—H12	108.9
C2—C3—C4	120.78 (17)	C13—C12—H12	108.9
C2—C3—H3	119.6	C14—C13—C12	111.87 (16)
C4—C3—H3	119.6	C14—C13—H13A	109.2
C9—C4—C3	117.57 (16)	C12—C13—H13A	109.2
C9—C4—C5	118.52 (16)	C14—C13—H13B	109.2
C3—C4—C5	123.91 (18)	C12—C13—H13B	109.2
C6—C5—C4	121.8 (2)	H13A—C13—H13B	107.9
C6—C5—H5	119.1	O1—C14—C15	122.46 (19)
C4—C5—H5	119.1	O1—C14—C13	121.3 (2)
C5—C6—C7	119.29 (18)	C15—C14—C13	116.24 (17)
C5—C6—C11	120.1 (2)	C20—C15—C16	118.8 (2)
C7—C6—C11	120.59 (19)	C20—C15—C14	120.37 (17)
C8—C7—C6	119.87 (17)	C16—C15—C14	120.79 (19)
C8—C7—C10	119.5 (2)	C17—C16—C15	121.0 (2)
C6—C7—C10	120.6 (2)	C17—C16—H16	119.5
C7—C8—C9	121.2 (2)	C15—C16—H16	119.5
C7—C8—H8	119.4	C16—C17—C18	120.1 (2)
C9—C8—H8	119.4	C16—C17—H17	119.9
N1—C9—C4	122.10 (15)	C18—C17—H17	119.9
N1—C9—C8	118.61 (18)	C19—C18—C17	120.4 (2)
C4—C9—C8	119.29 (17)	C19—C18—H18	119.8
C7—C10—H10A	109.5	C17—C18—H18	119.8
C7—C10—H10B	109.5	C18—C19—C20	120.5 (2)
H10A—C10—H10B	109.5	C18—C19—H19	119.7
C7—C10—H10C	109.5	C20—C19—H19	119.7
H10A—C10—H10C	109.5	N2—C20—C19	120.17 (18)
H10B—C10—H10C	109.5	N2—C20—C15	120.66 (18)
C6—C11—H11A	109.5	C19—C20—C15	119.16 (18)
C6—C11—H11B	109.5	C1—N1—C9	117.23 (16)
H11A—C11—H11B	109.5	C20—N2—C12	115.66 (15)
C6—C11—H11C	109.5	C20—N2—H2N	111.0 (14)
H11A—C11—H11C	109.5	C12—N2—H2N	114.5 (15)

N1—C1—C2—C3	1.6 (3)	N2—C12—C13—C14	−55.2 (2)
Cl1—C1—C2—C3	−178.31 (14)	C2—C12—C13—C14	−176.88 (16)
N1—C1—C2—C12	−179.75 (18)	C12—C13—C14—O1	−153.6 (2)
Cl1—C1—C2—C12	0.3 (2)	C12—C13—C14—C15	28.1 (2)
C1—C2—C3—C4	−0.1 (3)	O1—C14—C15—C20	−176.5 (2)
C12—C2—C3—C4	−178.73 (16)	C13—C14—C15—C20	1.8 (3)
C2—C3—C4—C9	−0.7 (3)	O1—C14—C15—C16	0.5 (3)
C2—C3—C4—C5	179.93 (18)	C13—C14—C15—C16	178.8 (2)
C9—C4—C5—C6	0.1 (3)	C20—C15—C16—C17	0.7 (4)
C3—C4—C5—C6	179.40 (19)	C14—C15—C16—C17	−176.3 (2)
C4—C5—C6—C7	−0.5 (3)	C15—C16—C17—C18	0.1 (4)
C4—C5—C6—C11	178.64 (19)	C16—C17—C18—C19	−0.3 (5)
C5—C6—C7—C8	0.9 (3)	C17—C18—C19—C20	−0.3 (4)
C11—C6—C7—C8	−178.26 (19)	C18—C19—C20—N2	−179.4 (2)
C5—C6—C7—C10	−179.1 (2)	C18—C19—C20—C15	1.1 (3)
C11—C6—C7—C10	1.7 (3)	C16—C15—C20—N2	179.17 (19)
C6—C7—C8—C9	−0.8 (3)	C14—C15—C20—N2	−3.8 (3)
C10—C7—C8—C9	179.2 (2)	C16—C15—C20—C19	−1.3 (3)
C3—C4—C9—N1	0.3 (3)	C14—C15—C20—C19	175.74 (18)
C5—C4—C9—N1	179.64 (17)	C2—C1—N1—C9	−2.1 (3)
C3—C4—C9—C8	−179.37 (17)	Cl1—C1—N1—C9	177.84 (13)
C5—C4—C9—C8	0.0 (3)	C4—C9—N1—C1	1.1 (3)
C7—C8—C9—N1	−179.27 (18)	C8—C9—N1—C1	−179.28 (17)
C7—C8—C9—C4	0.4 (3)	C19—C20—N2—C12	153.97 (18)
C3—C2—C12—N2	−30.9 (2)	C15—C20—N2—C12	−26.5 (2)
C1—C2—C12—N2	150.56 (17)	C2—C12—N2—C20	177.70 (15)
C3—C2—C12—C13	89.7 (2)	C13—C12—N2—C20	55.4 (2)
C1—C2—C12—C13	−88.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N1ⁱ	0.86 (2)	2.53 (2)	3.297 (2)	148.6 (18)

Symmetry code: (i) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇ClN₂O
M_r	336.81
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.7345 (4), 10.6196 (6), 11.3463 (4)
α, β, γ (°)	96.425 (2), 100.068 (3), 109.576 (1)
V (Å³)	849.84 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
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	7058, 3863, 2507
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.133, 1.00
No. of reflections	3863
No. of parameters	222
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR2002 (Burla et al., 2005), 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
N2—H2N···N1ⁱ	0.86 (2)	2.53 (2)	3.297 (2)	148.6 (18)

Symmetry code: (i) −x, −y, −z+2.

Acknowledgements

We are grateful to all personnel of the PHYSYNOR laboratory, Université Mentouri-Constantine, Algeria, for their assistance. Thanks are due to the MESRS (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique - Algeria) for financial support.

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