Ethyl 4-(2-chloro­quinolin-3-yl)-1-phenyl-1H-pyrrole-3-carboxyl­ate

Benzerka, S.; Bouraiou, A.; Bouacida, S.; Debache, A.; Belfaitah, A.

doi:10.1107/S1600536808032546

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Pages o2115-o2116

doi:10.1107/S1600536808032546

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Ethyl 4-(2-chloroquinolin-3-yl)-1-phenyl-1H-pyrrole-3-carboxylate

Saida Benzerka,^a Abdelmalek Bouraiou,^a Sofiane Bouacida,^b,^c ^* Abdelmadjid Debache ^a and Ali Belfaitah ^a

^aLaboratoire des Produits Naturels d'Origine Végétale et de Synthèse Organique, PHYSYNOR, Université Mentouri-Constantine, 25000 Constantine, Algeria, ^bLaboratoire de Chimie Moléculaire, du Contrôle de l'Environnement et de Mesures Physico-Chimiques, Faculté des Sciences, Département de Chimie, Université Mentouri, 25000 Constantine, Algeria, and ^cDépartement de Chimie, Faculté des Sciences et Sciences de l'Ingénieur, Université A.Mira de Béjaia, Route Targua Ouzmour 06000 Béjaia, Algeria
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 27 September 2008; accepted 8 October 2008; online 15 October 2008)

In the molecule of the title compound, C₂₂H₁₇ClN₂O₂, the dihedral angles formed by the pyrrole ring with the quinoline and phenyl rings are 67.93 (8) and 28.40 (11)°, respectively. In the crystal structure, molecules are linked into dimers by intermolecular C—H⋯O hydrogen bonds.

Related literature

For general background, see: Corvo & Pereira (2002 ); Harrison et al. (2006 ); Wright et al. (2001 ); Sahu et al. (2002 ); Michael (1997 ); Rezig et al. (2000 ); Raj Amal et al. (2003 ); Witherup et al. (1995 ); Moussaoui et al. (2002 ). For related structures, see: Belfaitah et al. (2006 ); Bouraiou et al. (2008 );. For details of the synthesis, see: Menasra et al. (2005 ); Benzerka et al. (2008 ). For pyrroles as building blocks in naturally occurring and biologically active compounds such as heme, chlorophyll and vitamin B12, see: Bigg & Bonnaud (1994 ); Demir et al. (2005 ); Tsukamoto et al. (2001 );

Experimental

Crystal data

C₂₂H₁₇ClN₂O₂
M_r = 376.83
Monoclinic, I 2/a
a = 20.2021 (6) Å
b = 8.0500 (1) Å
c = 24.0238 (7) Å
β = 105.29 (2)°
V = 3768.6 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 (2) K
0.15 × 0.06 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
9812 measured reflections
3315 independent reflections
2343 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.142
S = 1.02
3315 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.29 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
C12—H12⋯O1ⁱ	0.93	2.50	3.383 (3)	159
C15—H15⋯O1ⁱ	0.93	2.45	3.275 (4)	148
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO/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/S1600536808032546/rz2251sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808032546/rz2251Isup2.hkl

checkCIF report

Comment top

Heterocyclic compounds and particularly five and six membered ring compounds occupy a prominent place among various classes of organic compounds for their diverse biological activities. Among a wide variety of heterocycles that have been explored for developing pharmaceutically important molecules (Raj Amal et al., 2003), quinolines have played an important role in medicine chemistry (Wright et al., 2001; Sahu et al., 2002). Some of them have received considerable attention due to their presence in numerous natural products along with their wide ranging application as drugs, pharmaceutical and agrochemicals (Michael, 1997). Pyrroles are an important class of heterocyclic compounds and are widely used in synthetic organic chemistry and material science (Corvo & Pereira, 2002; Harrison et al., 2006). Pyrroles are often seen as building blocks in naturally occurring and biologically active compounds such as heme, chlorophyll and vitamin B12 (Demir et al., 2005; Bigg & Bonnaud, 1994; Tsukamoto et al., 2001). Syntheses of pyrroloquinolines derivatives were not particularly numerous in the literature before the initial report of the unique alkaloids (Witherup et al., 1995). In a continuation of our program on the synthesis and biological evaluation of quinolines derivatives (Belfaitah et al., 2006; Bouraiou et al., 2008; Rezig et al., 2000; Moussaoui et al., 2002), we have elaborated an efficient route for the synthesis of 3-pyrrolylquinolines by dehydrogenation of 3-pyrrolidinyl quinolines using activated manganese dioxide in refluxing THF during 5 h (Menasra et al., 2005; Benzerka et al. 2008). We report here the crystal structure of a new N-phenylpyrrole derivative bearing a quinoline ring at C-3 and an ester group at C-4.

The molecular structure and the atom-numbering scheme of the title compound are shown in Fig. 1. The quinoline ring system is essentially planar, the dihedral angle formed by the six-membered rings being only 0.64 (8)°. The dihedral angles between the pyrrole ring and the quinoline and phenyl rings are 67.93 (8) and 28.40 (11)°, respectively. The geometric parameters 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). In the crystal structure (Fig. 2), molecules are linked into dimers by intermolecular C—H···O hydrogen bonds (Table 1).

Related literature top

For general background, see: Corvo & Pereira (2002); Harrison et al. (2006); Wright et al. (2001); Sahu et al. (2002); Michael (1997); Rezig et al. (2000); Raj Amal et al. (2003); Witherup et al. (1995); Moussaoui et al., 2002). For related structures, see: Belfaitah et al. (2006); Bouraiou et al. (2008);. For details of the synthesis, see: Menasra et al. (2005); Benzerka et al. (2008). For pyrroles as building blocks in naturally occurring and biologically active compounds such as heme, chlorophyll and vitamin B12, see: Bigg & Bonnaud (1994); Demir et al. (2005); Tsukamoto et al. (2001);

Experimental top

To a 0.1 M solution of ethyl 4-(2-chloroquinolin-3-yl)-1-phenylpyrrole -3-carboxylate (1.5 mmol) in dry THF (15 ml) 2.5 equivalents of activated MnO₂ were added. The mixture was refluxed for 2.5 h. The same amount of activated MnO₂ was then added, and the reflux was continued for an additional 2.5 h. After cooling, the mixture was diluted with THF, filtered through Celite and washed with THF (5x5 ml). The filtrate was concentrated under reduced pressure, diluted with CH₂Cl₂ and washed with water (2x5 ml). The organic layers were separated and dried over anhydrous MgSO₄. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel using AcOEt/pentane (2:1 v/v) as eluent to afford the corresponding pure pyrrole derivative. Crystals suitable for X-ray analysis were obtained by slow evaporation of the solvent.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/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 molecular structure of the title compound with the atomic labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram of the title compound viewed along the b axis.

Ethyl 4-(2-chloroquinolin-3-yl)-1-phenyl-1H-pyrrole-3-carboxylate top

Crystal data top

C₂₂H₁₇ClN₂O₂	F(000) = 1568
M_r = 376.83	D_x = 1.328 Mg m⁻³
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2ya	Cell parameters from 9812 reflections
a = 20.2021 (6) Å	θ = 5.1–25.1°
b = 8.0500 (1) Å	µ = 0.22 mm⁻¹
c = 24.0238 (7) Å	T = 296 K
β = 105.29 (2)°	Needle, white
V = 3768.6 (4) Å³	0.15 × 0.06 × 0.05 mm
Z = 8

Data collection top

Nonius KappaCCD diffractometer	2343 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.043
Graphite monochromator	θ_max = 25.1°, θ_min = 5.1°
ϕ scans, and ω scans with κ offsets	h = −23→24
9812 measured reflections	k = −9→9
3315 independent reflections	l = −28→28

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.103P)² + 0.3358P] where P = (F_o² + 2F_c²)/3
3315 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₂H₁₇ClN₂O₂	V = 3768.6 (4) Å³
M_r = 376.83	Z = 8
Monoclinic, I2/a	Mo Kα radiation
a = 20.2021 (6) Å	µ = 0.22 mm⁻¹
b = 8.0500 (1) Å	T = 296 K
c = 24.0238 (7) Å	0.15 × 0.06 × 0.05 mm
β = 105.29 (2)°

Data collection top

Nonius KappaCCD diffractometer	2343 reflections with I > 2σ(I)
9812 measured reflections	R_int = 0.043
3315 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 1.02	Δρ_max = 0.29 e Å⁻³
3315 reflections	Δρ_min = −0.27 e Å⁻³
244 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	0.12476 (3)	0.20796 (10)	0.35827 (3)	0.0669 (3)
O1	0.19940 (10)	−0.3023 (3)	0.31308 (8)	0.0722 (6)
C13	0.12321 (12)	−0.1022 (3)	0.25970 (10)	0.0454 (6)
N2	0.10945 (10)	0.0124 (3)	0.17336 (8)	0.0480 (5)
N1	0.00661 (12)	0.1516 (3)	0.37746 (9)	0.0607 (6)
C3	−0.04742 (13)	−0.0147 (3)	0.27328 (11)	0.0515 (6)
H3	−0.0658	−0.0671	0.2381	0.062*
O2	0.11506 (10)	−0.2065 (3)	0.34790 (8)	0.0696 (6)
C20	0.15071 (12)	−0.2127 (3)	0.30819 (10)	0.0489 (6)
C12	0.14907 (12)	−0.0931 (3)	0.21243 (10)	0.0483 (6)
H12	0.1874	−0.1498	0.2079	0.058*
C1	0.04143 (13)	0.1247 (3)	0.34028 (10)	0.0509 (6)
C14	0.12066 (13)	0.0599 (3)	0.11921 (10)	0.0507 (6)
C10	0.06434 (12)	0.0057 (3)	0.24895 (10)	0.0445 (5)
C11	0.05718 (12)	0.0714 (3)	0.19565 (10)	0.0490 (6)
H11	0.0227	0.1444	0.1770	0.059*
C2	0.01905 (12)	0.0392 (3)	0.28691 (10)	0.0455 (6)
C4	−0.08852 (13)	0.0083 (3)	0.31192 (12)	0.0555 (7)
C9	−0.05921 (14)	0.0900 (4)	0.36430 (12)	0.0601 (7)
C5	−0.15703 (14)	−0.0503 (4)	0.30059 (15)	0.0705 (8)
H5	−0.1772	−0.1042	0.2660	0.085*
C16	0.19620 (18)	0.1089 (5)	0.05969 (13)	0.0772 (9)
H16	0.2402	0.1075	0.0546	0.093*
C15	0.18577 (15)	0.0595 (4)	0.11161 (12)	0.0635 (7)
H15	0.2228	0.0258	0.1415	0.076*
C7	−0.1635 (2)	0.0529 (5)	0.39232 (18)	0.0898 (11)
H7	−0.1889	0.0675	0.4190	0.108*
C6	−0.19327 (17)	−0.0274 (4)	0.34045 (18)	0.0827 (10)
H6	−0.2382	−0.0658	0.3330	0.099*
C8	−0.09838 (17)	0.1100 (5)	0.40466 (15)	0.0802 (10)
H8	−0.0793	0.1626	0.4397	0.096*
C19	0.06632 (17)	0.1077 (5)	0.07449 (12)	0.0823 (10)
H19	0.0219	0.1053	0.0788	0.099*
C17	0.14196 (19)	0.1601 (5)	0.01550 (13)	0.0817 (10)
H17	0.1492	0.1950	−0.0193	0.098*
C21	0.1396 (2)	−0.3041 (5)	0.39981 (13)	0.0838 (10)
H21A	0.1874	−0.3336	0.4046	0.101*
H21B	0.1132	−0.4057	0.3970	0.101*
C18	0.07782 (19)	0.1593 (6)	0.02294 (13)	0.0936 (12)
H18	0.0410	0.1940	−0.0070	0.112*
C22	0.1328 (3)	−0.2075 (6)	0.44902 (17)	0.141 (2)
H22A	0.1489	−0.2719	0.4836	0.211*
H22B	0.0855	−0.1791	0.4441	0.211*
H22C	0.1596	−0.1078	0.4519	0.211*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0655 (4)	0.0788 (5)	0.0550 (4)	−0.0096 (4)	0.0136 (3)	−0.0156 (3)
O1	0.0693 (12)	0.0869 (15)	0.0660 (12)	0.0322 (12)	0.0276 (10)	0.0229 (11)
C13	0.0496 (12)	0.0459 (14)	0.0408 (12)	0.0020 (11)	0.0120 (10)	−0.0005 (10)
N2	0.0535 (11)	0.0519 (12)	0.0399 (10)	0.0034 (10)	0.0144 (9)	0.0006 (9)
N1	0.0674 (14)	0.0676 (15)	0.0516 (12)	0.0092 (12)	0.0239 (11)	−0.0019 (11)
C3	0.0547 (14)	0.0473 (15)	0.0517 (14)	0.0051 (11)	0.0127 (11)	0.0025 (11)
O2	0.0821 (13)	0.0810 (14)	0.0542 (11)	0.0318 (11)	0.0330 (10)	0.0230 (10)
C20	0.0540 (14)	0.0486 (14)	0.0461 (13)	0.0043 (12)	0.0170 (11)	0.0016 (11)
C12	0.0521 (13)	0.0487 (15)	0.0456 (13)	0.0050 (11)	0.0154 (11)	0.0002 (11)
C1	0.0578 (14)	0.0514 (15)	0.0443 (13)	0.0036 (12)	0.0153 (11)	−0.0017 (11)
C14	0.0635 (15)	0.0514 (15)	0.0379 (12)	0.0035 (12)	0.0143 (11)	0.0013 (11)
C10	0.0483 (12)	0.0434 (13)	0.0413 (12)	0.0015 (11)	0.0112 (10)	−0.0039 (10)
C11	0.0502 (13)	0.0497 (14)	0.0466 (13)	0.0060 (11)	0.0116 (10)	−0.0004 (11)
C2	0.0512 (13)	0.0424 (14)	0.0428 (13)	0.0056 (10)	0.0124 (10)	0.0010 (10)
C4	0.0578 (15)	0.0498 (15)	0.0622 (16)	0.0104 (12)	0.0219 (12)	0.0127 (13)
C9	0.0659 (16)	0.0611 (18)	0.0589 (16)	0.0149 (14)	0.0262 (13)	0.0082 (13)
C5	0.0592 (16)	0.0652 (19)	0.091 (2)	0.0067 (14)	0.0263 (16)	0.0113 (16)
C16	0.088 (2)	0.093 (2)	0.0613 (18)	0.0162 (19)	0.0381 (16)	0.0154 (17)
C15	0.0694 (17)	0.0738 (19)	0.0515 (15)	0.0134 (15)	0.0235 (13)	0.0112 (14)
C7	0.089 (2)	0.103 (3)	0.095 (3)	0.020 (2)	0.054 (2)	0.016 (2)
C6	0.0617 (17)	0.078 (2)	0.117 (3)	0.0093 (17)	0.0390 (19)	0.025 (2)
C8	0.083 (2)	0.094 (3)	0.078 (2)	0.0131 (19)	0.0467 (18)	0.0042 (18)
C19	0.0695 (18)	0.125 (3)	0.0500 (16)	0.014 (2)	0.0121 (14)	0.0124 (18)
C17	0.110 (3)	0.094 (3)	0.0478 (16)	0.016 (2)	0.0330 (17)	0.0147 (16)
C21	0.113 (3)	0.089 (2)	0.0569 (18)	0.034 (2)	0.0361 (17)	0.0305 (17)
C18	0.092 (2)	0.138 (4)	0.0473 (17)	0.025 (2)	0.0121 (16)	0.0218 (19)
C22	0.245 (6)	0.113 (4)	0.061 (2)	0.023 (4)	0.035 (3)	0.017 (2)

Geometric parameters (Å, º) top

Cl1—C1	1.757 (3)	C9—C8	1.413 (4)
O1—C20	1.200 (3)	C5—C6	1.362 (4)
C13—C12	1.371 (3)	C5—H5	0.9300
C13—C10	1.440 (3)	C16—C17	1.373 (5)
C13—C20	1.454 (3)	C16—C15	1.377 (4)
N2—C12	1.359 (3)	C16—H16	0.9300
N2—C11	1.388 (3)	C15—H15	0.9300
N2—C14	1.430 (3)	C7—C8	1.350 (5)
N1—C1	1.293 (3)	C7—C6	1.392 (5)
N1—C9	1.376 (4)	C7—H7	0.9300
C3—C2	1.366 (3)	C6—H6	0.9300
C3—C4	1.411 (3)	C8—H8	0.9300
C3—H3	0.9300	C19—C18	1.383 (4)
O2—C20	1.339 (3)	C19—H19	0.9300
O2—C21	1.446 (3)	C17—C18	1.354 (5)
C12—H12	0.9300	C17—H17	0.9300
C1—C2	1.420 (3)	C21—C22	1.451 (5)
C14—C19	1.373 (4)	C21—H21A	0.9700
C14—C15	1.375 (4)	C21—H21B	0.9700
C10—C11	1.357 (3)	C18—H18	0.9300
C10—C2	1.477 (3)	C22—H22A	0.9600
C11—H11	0.9300	C22—H22B	0.9600
C4—C9	1.405 (4)	C22—H22C	0.9600
C4—C5	1.419 (4)

C12—C13—C10	107.2 (2)	C6—C5—H5	120.1
C12—C13—C20	123.2 (2)	C4—C5—H5	120.1
C10—C13—C20	129.5 (2)	C17—C16—C15	120.4 (3)
C12—N2—C11	108.49 (19)	C17—C16—H16	119.8
C12—N2—C14	126.1 (2)	C15—C16—H16	119.8
C11—N2—C14	125.3 (2)	C14—C15—C16	120.0 (3)
C1—N1—C9	116.8 (2)	C14—C15—H15	120.0
C2—C3—C4	120.8 (2)	C16—C15—H15	120.0
C2—C3—H3	119.6	C8—C7—C6	121.4 (3)
C4—C3—H3	119.6	C8—C7—H7	119.3
C20—O2—C21	117.9 (2)	C6—C7—H7	119.3
O1—C20—O2	122.2 (2)	C5—C6—C7	120.4 (3)
O1—C20—C13	125.2 (2)	C5—C6—H6	119.8
O2—C20—C13	112.6 (2)	C7—C6—H6	119.8
N2—C12—C13	108.8 (2)	C7—C8—C9	120.0 (4)
N2—C12—H12	125.6	C7—C8—H8	120.0
C13—C12—H12	125.6	C9—C8—H8	120.0
N1—C1—C2	127.1 (2)	C14—C19—C18	119.8 (3)
N1—C1—Cl1	115.3 (2)	C14—C19—H19	120.1
C2—C1—Cl1	117.60 (18)	C18—C19—H19	120.1
C19—C14—C15	119.5 (2)	C18—C17—C16	119.5 (3)
C19—C14—N2	120.1 (2)	C18—C17—H17	120.2
C15—C14—N2	120.4 (2)	C16—C17—H17	120.2
C11—C10—C13	106.4 (2)	O2—C21—C22	109.1 (3)
C11—C10—C2	125.6 (2)	O2—C21—H21A	109.9
C13—C10—C2	128.0 (2)	C22—C21—H21A	109.9
C10—C11—N2	109.1 (2)	O2—C21—H21B	109.9
C10—C11—H11	125.4	C22—C21—H21B	109.9
N2—C11—H11	125.4	H21A—C21—H21B	108.3
C3—C2—C1	115.4 (2)	C17—C18—C19	120.8 (3)
C3—C2—C10	121.6 (2)	C17—C18—H18	119.6
C1—C2—C10	123.0 (2)	C19—C18—H18	119.6
C9—C4—C3	117.9 (2)	C21—C22—H22A	109.5
C9—C4—C5	119.1 (3)	C21—C22—H22B	109.5
C3—C4—C5	122.9 (3)	H22A—C22—H22B	109.5
N1—C9—C4	121.9 (2)	C21—C22—H22C	109.5
N1—C9—C8	118.9 (3)	H22A—C22—H22C	109.5
C4—C9—C8	119.2 (3)	H22B—C22—H22C	109.5
C6—C5—C4	119.9 (3)

C21—O2—C20—O1	4.1 (4)	Cl1—C1—C2—C10	5.3 (3)
C21—O2—C20—C13	−176.6 (3)	C11—C10—C2—C3	67.9 (4)
C12—C13—C20—O1	2.5 (4)	C13—C10—C2—C3	−111.1 (3)
C10—C13—C20—O1	178.0 (3)	C11—C10—C2—C1	−113.8 (3)
C12—C13—C20—O2	−176.7 (2)	C13—C10—C2—C1	67.2 (4)
C10—C13—C20—O2	−1.3 (4)	C2—C3—C4—C9	0.8 (4)
C11—N2—C12—C13	−0.3 (3)	C2—C3—C4—C5	−177.9 (3)
C14—N2—C12—C13	177.7 (2)	C1—N1—C9—C4	−2.8 (4)
C10—C13—C12—N2	−0.5 (3)	C1—N1—C9—C8	177.4 (3)
C20—C13—C12—N2	175.8 (2)	C3—C4—C9—N1	2.2 (4)
C9—N1—C1—C2	0.4 (4)	C5—C4—C9—N1	−179.1 (3)
C9—N1—C1—Cl1	179.1 (2)	C3—C4—C9—C8	−178.0 (3)
C12—N2—C14—C19	153.2 (3)	C5—C4—C9—C8	0.7 (4)
C11—N2—C14—C19	−29.2 (4)	C9—C4—C5—C6	−0.3 (4)
C12—N2—C14—C15	−27.3 (4)	C3—C4—C5—C6	178.4 (3)
C11—N2—C14—C15	150.3 (3)	C19—C14—C15—C16	0.9 (5)
C12—C13—C10—C11	1.1 (3)	N2—C14—C15—C16	−178.6 (3)
C20—C13—C10—C11	−174.9 (2)	C17—C16—C15—C14	0.5 (5)
C12—C13—C10—C2	−179.8 (2)	C4—C5—C6—C7	−0.1 (5)
C20—C13—C10—C2	4.2 (4)	C8—C7—C6—C5	0.0 (6)
C13—C10—C11—N2	−1.2 (3)	C6—C7—C8—C9	0.5 (6)
C2—C10—C11—N2	179.6 (2)	N1—C9—C8—C7	179.0 (3)
C12—N2—C11—C10	1.0 (3)	C4—C9—C8—C7	−0.9 (5)
C14—N2—C11—C10	−177.0 (2)	C15—C14—C19—C18	−1.9 (5)
C4—C3—C2—C1	−2.9 (4)	N2—C14—C19—C18	177.6 (3)
C4—C3—C2—C10	175.5 (2)	C15—C16—C17—C18	−1.0 (6)
N1—C1—C2—C3	2.4 (4)	C20—O2—C21—C22	139.1 (4)
Cl1—C1—C2—C3	−176.30 (19)	C16—C17—C18—C19	0.0 (6)
N1—C1—C2—C10	−176.0 (3)	C14—C19—C18—C17	1.5 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.93	2.50	3.383 (3)	159
C15—H15···O1ⁱ	0.93	2.45	3.275 (4)	148

Symmetry code: (i) −x+1/2, −y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇ClN₂O₂
M_r	376.83
Crystal system, space group	Monoclinic, I2/a
Temperature (K)	296
a, b, c (Å)	20.2021 (6), 8.0500 (1), 24.0238 (7)
β (°)	105.29 (2)
V (Å³)	3768.6 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
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	9812, 3315, 2343
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.142, 1.02
No. of reflections	3315
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.27

Computer programs: COLLECT (Nonius, 1998), DENZO/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
C12—H12···O1ⁱ	0.9300	2.5000	3.383 (3)	159.00
C15—H15···O1ⁱ	0.9300	2.4500	3.275 (4)	148.00

Symmetry code: (i) −x+1/2, −y−1/2, −z+1/2.

Acknowledgements

We are grateful to Professor Lahcéne Ouahab (Organométalliques et materiaux moléculaire, Université de Rennes I, France) for data-collection facilities and to Professor Salah Rhouati (PHYSYNOR, Université Mentouri Constantine, Algérie) for his assistance. Thanks are due to MESRS (Ministére de l'enseignement supérieur et de la recherche scientifique) for financial support.

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