(3RS,4SR)-Methyl 4-(2-chloro-5,8-di-methoxy-quinolin-3-yl)-1-phenyl-pyrrolidine-3-carboxyl-ate.

The mol-ecule of the title compound, C(23)H(23)ClN(2)O(4), contains a quinolyl unit linked to a functionalized pyrrolidine system with a 3,4-trans arrangement of the substituents. The unit cell contains two stereoisomers that have the absolute stereochemistry 3S,4R and 3R,4S. The pyrrolidine ring adopts a twist conformation with pseudo-rotation parameters P = 258.2 (3)° and τ(M) = 35.3 (1)°. The packing is stabilized by C-H⋯π inter-actions and offset π-π stacking (centroid-to-centroid distance = 3.849 Å, inter-planar distance = 3.293 Å and slippage = 1.994 Å) between phenyl rings, leading to a two-dimensional network.

Related literature

For general background, see: Padwa et al. (1999 ▶); Sahu et al. (2002 ▶); Robert & Meunier (1998 ▶); Dow et al. (2006 ▶); Witherup et al. (1995 ▶); Kravchenko et al. (2005 ▶); Bouraiou et al. (2008 ▶); Rezig et al. (2000 ▶); Moussaoui et al. (2002 ▶); Menasra et al. (2005 ▶); Rao et al. (1981 ▶). For related structures, see: Belfaitah et al. (2006 ▶); Bouraiou et al. (2007a ▶,b ▶).

Experimental

Crystal data

C23H23ClN2O4

M = 426.88

Monoclinic,

a = 9.579 (1) Å

b = 17.518 (1) Å

c = 12.944 (2) Å

β = 109.01 (2)°

V = 2053.6 (5) Å3

Z = 4

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

9271 measured reflections

4717 independent reflections

3062 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.178

S = 1.03

4717 reflections

274 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.33 e Å−3

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: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and CAMERON (Pearce et al., 2000 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031838/dn2384sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031838/dn2384Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H23ClN2O4	F(000) = 896
Mr = 426.88	Dx = 1.381 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4717 reflections
a = 9.579 (1) Å	θ = 2.0–27.5°
b = 17.518 (1) Å	µ = 0.22 mm−1
c = 12.944 (2) Å	T = 296 K
β = 109.01 (2)°	Needle, white
V = 2053.6 (5) Å3	0.15 × 0.06 × 0.05 mm
Z = 4

Nonius KappaCCD diffractometer	3062 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 27.5°, θmin = 2.0°
φ scans, and ω scans with κ offsets	h = −12→12
9271 measured reflections	k = −22→22
4717 independent reflections	l = −16→16

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.102P)2 + 0.336P] where P = (Fo2 + 2Fc2)/3
4717 reflections	(Δ/σ)max < 0.001
274 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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
C2	0.4396 (2)	0.31838 (12)	−0.07671 (19)	0.0457 (5)
C3	0.3691 (3)	0.26052 (12)	−0.03567 (19)	0.0482 (5)
C4	0.3895 (3)	0.18796 (12)	−0.0673 (2)	0.0494 (5)
H4	0.3446	0.1473	−0.0443	0.059*
C5	0.4777 (2)	0.17338 (11)	−0.13446 (18)	0.0417 (5)
C6	0.5028 (3)	0.09863 (12)	−0.16864 (19)	0.0463 (5)
C7	0.5869 (3)	0.08969 (13)	−0.2347 (2)	0.0514 (5)
H7	0.6021	0.0411	−0.2580	0.062*
C8	0.6515 (3)	0.15355 (14)	−0.2683 (2)	0.0526 (6)
H8	0.7089	0.1461	−0.3131	0.063*
C9	0.6317 (2)	0.22567 (13)	−0.23653 (18)	0.0465 (5)
C10	0.5433 (2)	0.23684 (12)	−0.16778 (17)	0.0417 (5)
C11	0.4590 (4)	−0.03500 (14)	−0.1605 (3)	0.0733 (8)
H11A	0.4239	−0.0394	−0.2387	0.110*
H11B	0.4054	−0.0697	−0.1300	0.110*
H11C	0.5623	−0.0473	−0.1334	0.110*
C12	0.7822 (3)	0.28219 (17)	−0.3307 (3)	0.0708 (8)
H12A	0.8597	0.2464	−0.2973	0.106*
H12B	0.8247	0.3308	−0.3377	0.106*
H12C	0.7244	0.2640	−0.4017	0.106*
C13	0.2718 (3)	0.27974 (13)	0.0337 (2)	0.0520 (6)
H13	0.3102	0.3251	0.0781	0.062*
C14	0.1144 (3)	0.29516 (14)	−0.0433 (2)	0.0559 (6)
H14	0.1170	0.3162	−0.1129	0.067*
C15	0.0444 (3)	0.21579 (13)	−0.0605 (2)	0.0548 (6)
H15A	−0.0596	0.2188	−0.0682	0.066*
H15B	0.0544	0.1921	−0.1255	0.066*
C16	0.2513 (3)	0.21506 (13)	0.10654 (19)	0.0487 (5)
H16A	0.3385	0.1830	0.1305	0.058*
H16B	0.2314	0.2351	0.1702	0.058*
C17	0.0583 (2)	0.11625 (12)	0.08000 (18)	0.0441 (5)
C18	−0.0791 (3)	0.08503 (13)	0.0195 (2)	0.0500 (5)
H18	−0.1277	0.1023	−0.0511	0.060*
C19	−0.1420 (3)	0.02882 (15)	0.0646 (2)	0.0619 (7)
H19	−0.2333	0.0089	0.0237	0.074*
C20	−0.0738 (3)	0.00156 (15)	0.1677 (3)	0.0694 (8)
H20	−0.1182	−0.0361	0.1971	0.083*
C21	0.0624 (3)	0.03104 (15)	0.2276 (2)	0.0651 (7)
H21	0.1104	0.0127	0.2976	0.078*
C22	0.1281 (3)	0.08755 (13)	0.1845 (2)	0.0519 (6)
H22	0.2199	0.1066	0.2259	0.062*
C23	0.0291 (3)	0.34891 (17)	0.0089 (3)	0.0662 (7)
C24	−0.1671 (4)	0.4343 (2)	−0.0293 (4)	0.1079 (13)
H24A	−0.2517	0.4048	−0.0297	0.162*
H24B	−0.1985	0.4769	−0.0781	0.162*
H24C	−0.1176	0.4527	0.0433	0.162*
Cl1	0.41733 (7)	0.41375 (3)	−0.04310 (5)	0.0582 (2)
N1	0.5228 (2)	0.30920 (10)	−0.13716 (15)	0.0447 (4)
N2	0.1249 (2)	0.17236 (11)	0.03698 (15)	0.0487 (5)
O1	0.4375 (2)	0.04110 (9)	−0.13011 (16)	0.0635 (5)
O2	0.6896 (2)	0.29035 (10)	−0.26382 (16)	0.0650 (5)
O3	0.0479 (4)	0.3523 (2)	0.1042 (3)	0.1496 (14)
O4	−0.0678 (3)	0.38737 (15)	−0.0644 (2)	0.0947 (8)

	U11	U22	U33	U12	U13	U23
C2	0.0513 (12)	0.0368 (10)	0.0521 (12)	−0.0025 (9)	0.0211 (10)	0.0011 (9)
C3	0.0518 (13)	0.0418 (11)	0.0572 (14)	−0.0015 (9)	0.0262 (11)	−0.0001 (9)
C4	0.0542 (13)	0.0390 (10)	0.0623 (14)	−0.0046 (9)	0.0292 (11)	0.0025 (10)
C5	0.0422 (11)	0.0385 (10)	0.0478 (12)	−0.0029 (8)	0.0192 (9)	0.0003 (8)
C6	0.0469 (12)	0.0387 (11)	0.0562 (13)	−0.0012 (9)	0.0210 (10)	−0.0010 (9)
C7	0.0578 (14)	0.0439 (11)	0.0571 (14)	0.0027 (10)	0.0249 (11)	−0.0048 (10)
C8	0.0566 (14)	0.0570 (13)	0.0535 (13)	0.0023 (11)	0.0306 (11)	0.0002 (10)
C9	0.0472 (12)	0.0485 (12)	0.0480 (12)	−0.0020 (9)	0.0215 (10)	0.0055 (9)
C10	0.0404 (11)	0.0412 (11)	0.0447 (12)	−0.0007 (8)	0.0155 (9)	0.0037 (8)
C11	0.088 (2)	0.0378 (12)	0.106 (2)	−0.0050 (13)	0.0492 (18)	−0.0099 (13)
C12	0.0718 (18)	0.0793 (18)	0.0783 (19)	0.0021 (14)	0.0476 (16)	0.0170 (15)
C13	0.0581 (14)	0.0469 (12)	0.0550 (14)	−0.0054 (10)	0.0239 (11)	−0.0039 (10)
C14	0.0670 (15)	0.0525 (13)	0.0547 (14)	0.0026 (11)	0.0288 (12)	0.0043 (11)
C15	0.0602 (14)	0.0527 (13)	0.0488 (13)	−0.0032 (11)	0.0142 (11)	0.0016 (10)
C16	0.0485 (12)	0.0512 (12)	0.0483 (12)	−0.0079 (10)	0.0183 (10)	−0.0035 (9)
C17	0.0476 (12)	0.0414 (10)	0.0514 (12)	−0.0012 (9)	0.0270 (10)	−0.0052 (9)
C18	0.0488 (13)	0.0509 (12)	0.0552 (13)	−0.0036 (10)	0.0238 (11)	−0.0106 (10)
C19	0.0585 (15)	0.0552 (13)	0.0839 (19)	−0.0132 (12)	0.0394 (14)	−0.0167 (13)
C20	0.081 (2)	0.0564 (15)	0.089 (2)	−0.0128 (14)	0.0530 (18)	0.0000 (14)
C21	0.0787 (18)	0.0627 (15)	0.0649 (16)	0.0021 (14)	0.0386 (14)	0.0115 (12)
C22	0.0537 (13)	0.0528 (13)	0.0548 (14)	−0.0039 (10)	0.0252 (11)	0.0017 (10)
C23	0.0716 (17)	0.0722 (17)	0.0677 (18)	0.0082 (14)	0.0403 (15)	0.0035 (14)
C24	0.075 (2)	0.119 (3)	0.134 (3)	0.026 (2)	0.040 (2)	−0.042 (3)
Cl1	0.0772 (4)	0.0366 (3)	0.0688 (4)	−0.0023 (3)	0.0349 (3)	−0.0035 (2)
N1	0.0473 (10)	0.0404 (9)	0.0491 (10)	−0.0048 (8)	0.0194 (8)	0.0008 (7)
N2	0.0488 (10)	0.0526 (11)	0.0449 (10)	−0.0100 (8)	0.0153 (8)	0.0012 (8)
O1	0.0766 (12)	0.0357 (8)	0.0950 (14)	−0.0065 (8)	0.0510 (11)	−0.0048 (8)
O2	0.0799 (12)	0.0537 (10)	0.0820 (13)	−0.0051 (9)	0.0546 (11)	0.0084 (8)
O3	0.196 (3)	0.168 (3)	0.098 (2)	0.098 (3)	0.065 (2)	0.008 (2)
O4	0.0841 (15)	0.1037 (17)	0.0949 (17)	0.0388 (13)	0.0272 (13)	−0.0179 (13)

C2—N1	1.296 (3)	C13—H13	0.9800
C2—C3	1.414 (3)	C14—C15	1.528 (3)
C2—Cl1	1.757 (2)	C14—C23	1.540 (4)
C3—C4	1.369 (3)	C14—H14	0.9800
C3—C13	1.528 (3)	C15—N2	1.460 (3)
C4—C5	1.419 (3)	C15—H15A	0.9700
C4—H4	0.9300	C15—H15B	0.9700
C5—C10	1.412 (3)	C16—N2	1.458 (3)
C5—C6	1.427 (3)	C16—H16A	0.9700
C6—C7	1.362 (3)	C16—H16B	0.9700
C6—O1	1.363 (3)	C17—N2	1.384 (3)
C7—C8	1.413 (3)	C17—C22	1.393 (3)
C7—H7	0.9300	C17—C18	1.405 (3)
C8—C9	1.361 (3)	C18—C19	1.379 (3)
C8—H8	0.9300	C18—H18	0.9300
C9—O2	1.358 (3)	C19—C20	1.368 (4)
C9—C10	1.427 (3)	C19—H19	0.9300
C10—N1	1.361 (3)	C20—C21	1.382 (4)
C11—O1	1.424 (3)	C20—H20	0.9300
C11—H11A	0.9600	C21—C22	1.384 (3)
C11—H11B	0.9600	C21—H21	0.9300
C11—H11C	0.9600	C22—H22	0.9300
C12—O2	1.434 (3)	C23—O3	1.190 (4)
C12—H12A	0.9600	C23—O4	1.281 (4)
C12—H12B	0.9600	C24—O4	1.439 (3)
C12—H12C	0.9600	C24—H24A	0.9600
C13—C16	1.527 (3)	C24—H24B	0.9600
C13—C14	1.536 (4)	C24—H24C	0.9600
N1—C2—C3	126.9 (2)	C13—C14—H14	110.4
N1—C2—Cl1	114.55 (15)	C23—C14—H14	110.4
C3—C2—Cl1	118.52 (17)	N2—C15—C14	105.40 (19)
C4—C3—C2	114.9 (2)	N2—C15—H15A	110.7
C4—C3—C13	123.70 (19)	C14—C15—H15A	110.7
C2—C3—C13	121.36 (19)	N2—C15—H15B	110.7
C3—C4—C5	121.5 (2)	C14—C15—H15B	110.7
C3—C4—H4	119.3	H15A—C15—H15B	108.8
C5—C4—H4	119.3	N2—C16—C13	104.32 (19)
C10—C5—C4	117.30 (19)	N2—C16—H16A	110.9
C10—C5—C6	119.41 (18)	C13—C16—H16A	110.9
C4—C5—C6	123.29 (18)	N2—C16—H16B	110.9
C7—C6—O1	125.5 (2)	C13—C16—H16B	110.9
C7—C6—C5	119.60 (19)	H16A—C16—H16B	108.9
O1—C6—C5	114.91 (18)	N2—C17—C22	120.6 (2)
C6—C7—C8	120.6 (2)	N2—C17—C18	121.5 (2)
C6—C7—H7	119.7	C22—C17—C18	117.8 (2)
C8—C7—H7	119.7	C19—C18—C17	120.1 (2)
C9—C8—C7	121.6 (2)	C19—C18—H18	120.0
C9—C8—H8	119.2	C17—C18—H18	120.0
C7—C8—H8	119.2	C20—C19—C18	121.8 (3)
O2—C9—C8	126.0 (2)	C20—C19—H19	119.1
O2—C9—C10	115.04 (19)	C18—C19—H19	119.1
C8—C9—C10	118.99 (19)	C19—C20—C21	118.7 (2)
N1—C10—C5	121.56 (18)	C19—C20—H20	120.6
N1—C10—C9	118.70 (18)	C21—C20—H20	120.6
C5—C10—C9	119.73 (19)	C20—C21—C22	120.8 (3)
O1—C11—H11A	109.5	C20—C21—H21	119.6
O1—C11—H11B	109.5	C22—C21—H21	119.6
H11A—C11—H11B	109.5	C21—C22—C17	120.8 (2)
O1—C11—H11C	109.5	C21—C22—H22	119.6
H11A—C11—H11C	109.5	C17—C22—H22	119.6
H11B—C11—H11C	109.5	O3—C23—O4	124.8 (3)
O2—C12—H12A	109.5	O3—C23—C14	124.3 (3)
O2—C12—H12B	109.5	O4—C23—C14	110.9 (2)
H12A—C12—H12B	109.5	O4—C24—H24A	109.5
O2—C12—H12C	109.5	O4—C24—H24B	109.5
H12A—C12—H12C	109.5	H24A—C24—H24B	109.5
H12B—C12—H12C	109.5	O4—C24—H24C	109.5
C16—C13—C3	115.15 (19)	H24A—C24—H24C	109.5
C16—C13—C14	103.61 (19)	H24B—C24—H24C	109.5
C3—C13—C14	108.3 (2)	C2—N1—C10	117.82 (18)
C16—C13—H13	109.8	C17—N2—C16	120.98 (18)
C3—C13—H13	109.8	C17—N2—C15	122.38 (19)
C14—C13—H13	109.8	C16—N2—C15	111.38 (18)
C15—C14—C13	103.03 (19)	C6—O1—C11	117.75 (19)
C15—C14—C23	110.5 (2)	C9—O2—C12	117.3 (2)
C13—C14—C23	111.8 (2)	C23—O4—C24	117.5 (3)
C15—C14—H14	110.4

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···Cg1i	0.96	2.67	3.601 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C17–C22 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12B⋯Cg1i	0.96	2.67	3.601 (3)	164

Symmetry code: (i) .