2-Ethyl-6-(2-pyrid-yl)-5,6,6a,11b-tetra-hydro-7H-indeno[2,1-c]quinoline.

The title compound, C(23)H(22)N(2), was obtained using the three-component imino Diels-Alder reaction via a one-pot condensation between anilines, α-pyridine-carboxy-aldehyde and indene using BF(3)·OEt(2) as the catalyst. The mol-ecular structure reveals the cis-form as the unique diastereoisomer. The crystal structure comprises one-dimensional zigzag ribbons connected via N-H⋯N hydrogen bonds. C-H⋯π inter-actions also occur.

Related literature

For background to polycyclic quinoline derivatives, see: Denny & Baguley (2003 ▶); Gelderblom & Sparreboom (2006 ▶). For the biological activity of quinolines, see: Ewesuedo et al. (2001 ▶); Ishida & Asao (2002 ▶); Kouznetsov et al. (2006 ▶); Li et al. (2006 ▶); Ohyama et al. (1999 ▶); Priel et al. (1991 ▶); Twelves et al. (1999 ▶); Martínez & Chacón-García (2005 ▶); Pommier (2006 ▶).

Experimental

Crystal data

C23H22N2

M = 326.43

Monoclinic,

a = 13.241 (4) Å

b = 15.801 (4) Å

c = 8.789 (2) Å

β = 101.168 (6)°

V = 1804.0 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.30 × 0.28 × 0.26 mm

Data collection

Rigaku AFC7S Mercury diffractometer

Absorption correction: multi-scan (Jacobson, 1998 ▶) T min = 0.971, T max = 0.981

20284 measured reflections

3688 independent reflections

2420 reflections with I > 2σ(I)

R int = 0.044

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.157

S = 1.07

3688 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL-NT and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536810005805/tk2615sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005805/tk2615Isup2.hkl

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

C23H22N2	F(000) = 696
Mr = 326.43	Dx = 1.202 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11041 reflections
a = 13.241 (4) Å	θ = 1.6–27.7°
b = 15.801 (4) Å	µ = 0.07 mm−1
c = 8.789 (2) Å	T = 293 K
β = 101.168 (6)°	Block, yellow
V = 1804.0 (8) Å3	0.30 × 0.28 × 0.26 mm
Z = 4

Rigaku AFC7S Mercury diffractometer	3688 independent reflections
Radiation source: Normal-focus sealed tube	2420 reflections with I > 2σ(I)
graphite	Rint = 0.044
ω scans	θmax = 28.0°, θmin = 2.0°
Absorption correction: multi-scan (Jacobson, 1998)	h = −15→15
Tmin = 0.971, Tmax = 0.981	k = −18→20
20284 measured reflections	l = −11→11

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0698P)2 + 0.2578P] where P = (Fo2 + 2Fc2)/3
3688 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.20 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
N1	0.02307 (11)	0.64024 (9)	0.43799 (17)	0.0490 (4)
H1N	−0.0192	0.6589	0.3565	0.059*
N2	−0.13358 (12)	0.73555 (10)	0.68890 (19)	0.0562 (4)
C1	0.00785 (13)	0.68474 (11)	0.5771 (2)	0.0460 (4)
H1	0.0242	0.7447	0.5668	0.055*
C2	0.07995 (13)	0.64878 (11)	0.7193 (2)	0.0458 (4)
H2	0.0741	0.6845	0.8084	0.055*
C3	0.05427 (14)	0.55713 (11)	0.7591 (2)	0.0528 (5)
H3A	0.0073	0.5563	0.8311	0.063*
H3B	0.0237	0.5261	0.6663	0.063*
C4	0.15662 (15)	0.52035 (11)	0.8317 (2)	0.0499 (5)
C5	0.17744 (17)	0.44613 (13)	0.9155 (2)	0.0636 (6)
H5	0.1240	0.4127	0.9366	0.076*
C6	0.2788 (2)	0.42241 (15)	0.9675 (3)	0.0744 (7)
H6	0.2934	0.3721	1.0223	0.089*
C7	0.35794 (19)	0.47219 (16)	0.9391 (3)	0.0766 (7)
H7	0.4257	0.4555	0.9753	0.092*
C8	0.33764 (16)	0.54720 (14)	0.8568 (2)	0.0653 (6)
H8	0.3915	0.5811	0.8387	0.078*
C9	0.23611 (14)	0.57118 (11)	0.8019 (2)	0.0485 (5)
C10	0.19475 (13)	0.64765 (11)	0.7040 (2)	0.0456 (4)
H10	0.2292	0.6992	0.7495	0.055*
C11	0.20897 (13)	0.63816 (10)	0.5372 (2)	0.0434 (4)
C12	0.30732 (15)	0.63126 (11)	0.5033 (2)	0.0523 (5)
H12	0.3636	0.6365	0.5845	0.063*
C13	0.32582 (15)	0.61707 (12)	0.3557 (2)	0.0540 (5)
C14	0.24015 (16)	0.60999 (12)	0.2362 (2)	0.0545 (5)
H14	0.2494	0.5997	0.1356	0.065*
C15	0.14227 (14)	0.61795 (11)	0.2647 (2)	0.0485 (5)
H15	0.0864	0.6128	0.1828	0.058*
C16	0.12446 (13)	0.63354 (10)	0.4138 (2)	0.0427 (4)
C17	0.43476 (17)	0.60998 (15)	0.3268 (3)	0.0731 (7)
H17A	0.4802	0.5943	0.4230	0.088*
H17B	0.4371	0.5649	0.2526	0.088*
C18	0.4737 (2)	0.6887 (2)	0.2677 (5)	0.1291 (13)
H18A	0.5427	0.6798	0.2520	0.194*
H18B	0.4734	0.7334	0.3416	0.194*
H18C	0.4303	0.7040	0.1710	0.194*
C19	−0.10323 (13)	0.67742 (11)	0.5962 (2)	0.0459 (4)
C20	−0.16803 (15)	0.61310 (12)	0.5276 (2)	0.0562 (5)
H20	−0.1446	0.5731	0.4650	0.067*
C21	−0.26739 (16)	0.60932 (13)	0.5534 (3)	0.0620 (6)
H21	−0.3120	0.5669	0.5082	0.074*
C22	−0.29921 (16)	0.66882 (15)	0.6463 (3)	0.0667 (6)
H22	−0.3660	0.6680	0.6650	0.080*
C23	−0.23034 (16)	0.73019 (14)	0.7117 (3)	0.0667 (6)
H23	−0.2525	0.7703	0.7755	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0429 (9)	0.0609 (9)	0.0431 (9)	0.0008 (7)	0.0077 (7)	−0.0047 (7)
N2	0.0480 (10)	0.0581 (10)	0.0636 (11)	0.0033 (7)	0.0136 (8)	−0.0097 (8)
C1	0.0445 (11)	0.0427 (9)	0.0513 (11)	−0.0007 (7)	0.0103 (8)	−0.0045 (8)
C2	0.0460 (11)	0.0466 (10)	0.0451 (10)	−0.0006 (7)	0.0091 (8)	−0.0094 (8)
C3	0.0511 (12)	0.0547 (11)	0.0533 (11)	−0.0027 (8)	0.0122 (9)	0.0011 (9)
C4	0.0565 (12)	0.0515 (11)	0.0408 (10)	0.0000 (8)	0.0067 (8)	−0.0038 (8)
C5	0.0707 (15)	0.0608 (13)	0.0563 (12)	−0.0049 (10)	0.0051 (11)	0.0056 (10)
C6	0.0868 (18)	0.0677 (14)	0.0625 (14)	0.0120 (13)	−0.0013 (13)	0.0099 (11)
C7	0.0646 (16)	0.0928 (17)	0.0676 (15)	0.0176 (13)	0.0005 (12)	0.0117 (13)
C8	0.0509 (13)	0.0838 (15)	0.0593 (13)	0.0032 (10)	0.0056 (10)	0.0078 (11)
C9	0.0475 (12)	0.0563 (11)	0.0402 (10)	0.0008 (8)	0.0050 (8)	−0.0065 (8)
C10	0.0439 (11)	0.0461 (10)	0.0461 (10)	−0.0033 (7)	0.0066 (8)	−0.0066 (8)
C11	0.0439 (11)	0.0418 (9)	0.0445 (10)	−0.0030 (7)	0.0086 (8)	−0.0019 (7)
C12	0.0436 (12)	0.0595 (12)	0.0526 (12)	−0.0034 (8)	0.0065 (9)	−0.0006 (9)
C13	0.0498 (12)	0.0606 (12)	0.0540 (12)	0.0000 (8)	0.0164 (10)	0.0008 (9)
C14	0.0591 (13)	0.0595 (12)	0.0478 (11)	−0.0007 (9)	0.0178 (10)	−0.0022 (9)
C15	0.0489 (12)	0.0524 (11)	0.0430 (10)	−0.0017 (8)	0.0060 (9)	−0.0009 (8)
C16	0.0423 (11)	0.0394 (9)	0.0471 (10)	−0.0024 (7)	0.0107 (8)	−0.0004 (7)
C17	0.0557 (14)	0.0962 (17)	0.0727 (15)	0.0020 (11)	0.0255 (12)	−0.0024 (13)
C18	0.085 (2)	0.129 (3)	0.188 (4)	−0.0048 (18)	0.064 (2)	0.038 (3)
C19	0.0462 (11)	0.0439 (10)	0.0474 (10)	0.0035 (8)	0.0083 (8)	−0.0001 (8)
C20	0.0514 (12)	0.0529 (11)	0.0651 (13)	−0.0019 (8)	0.0134 (10)	−0.0089 (9)
C21	0.0496 (13)	0.0631 (13)	0.0738 (15)	−0.0089 (9)	0.0129 (11)	−0.0028 (11)
C22	0.0467 (12)	0.0813 (15)	0.0751 (15)	−0.0015 (11)	0.0192 (11)	−0.0010 (12)
C23	0.0532 (14)	0.0742 (14)	0.0765 (15)	0.0050 (10)	0.0218 (11)	−0.0149 (11)

N1—C16	1.403 (2)	C10—H10	0.9800
N1—C1	1.458 (2)	C11—C12	1.395 (3)
N1—H1N	0.8700	C11—C16	1.401 (2)
N2—C23	1.337 (2)	C12—C13	1.384 (3)
N2—C19	1.340 (2)	C12—H12	0.9300
C1—C19	1.517 (2)	C13—C14	1.393 (3)
C1—C2	1.528 (2)	C13—C17	1.516 (3)
C1—H1	0.9800	C14—C15	1.373 (3)
C2—C3	1.543 (2)	C14—H14	0.9300
C2—C10	1.552 (2)	C15—C16	1.397 (2)
C2—H2	0.9800	C15—H15	0.9300
C3—C4	1.499 (3)	C17—C18	1.479 (3)
C3—H3A	0.9700	C17—H17A	0.9700
C3—H3B	0.9700	C17—H17B	0.9700
C4—C5	1.384 (3)	C18—H18A	0.9600
C4—C9	1.389 (3)	C18—H18B	0.9600
C5—C6	1.383 (3)	C18—H18C	0.9600
C5—H5	0.9300	C19—C20	1.390 (3)
C6—C7	1.371 (3)	C20—C21	1.379 (3)
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.387 (3)	C21—C22	1.364 (3)
C7—H7	0.9300	C21—H21	0.9300
C8—C9	1.390 (3)	C22—C23	1.378 (3)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.522 (2)	C23—H23	0.9300
C10—C11	1.521 (2)
C16—N1—C1	117.08 (14)	C12—C11—C16	118.00 (17)
C16—N1—H1N	112.5	C12—C11—C10	120.53 (16)
C1—N1—H1N	110.8	C16—C11—C10	121.44 (16)
C23—N2—C19	117.16 (17)	C13—C12—C11	123.67 (18)
N1—C1—C19	110.52 (14)	C13—C12—H12	118.2
N1—C1—C2	109.93 (14)	C11—C12—H12	118.2
C19—C1—C2	110.28 (14)	C12—C13—C14	116.96 (18)
N1—C1—H1	108.7	C12—C13—C17	121.04 (18)
C19—C1—H1	108.7	C14—C13—C17	122.00 (18)
C2—C1—H1	108.7	C15—C14—C13	120.98 (18)
C1—C2—C3	113.82 (14)	C15—C14—H14	119.5
C1—C2—C10	113.60 (14)	C13—C14—H14	119.5
C3—C2—C10	105.75 (14)	C14—C15—C16	121.60 (17)
C1—C2—H2	107.8	C14—C15—H15	119.2
C3—C2—H2	107.8	C16—C15—H15	119.2
C10—C2—H2	107.8	C15—C16—C11	118.71 (17)
C4—C3—C2	103.86 (15)	C15—C16—N1	119.70 (16)
C4—C3—H3A	111.0	C11—C16—N1	121.53 (16)
C2—C3—H3A	111.0	C18—C17—C13	113.9 (2)
C4—C3—H3B	111.0	C18—C17—H17A	108.8
C2—C3—H3B	111.0	C13—C17—H17A	108.8
H3A—C3—H3B	109.0	C18—C17—H17B	108.8
C5—C4—C9	120.69 (18)	C13—C17—H17B	108.8
C5—C4—C3	128.74 (18)	H17A—C17—H17B	107.7
C9—C4—C3	110.56 (16)	C17—C18—H18A	109.5
C6—C5—C4	119.1 (2)	C17—C18—H18B	109.5
C6—C5—H5	120.5	H18A—C18—H18B	109.5
C4—C5—H5	120.5	C17—C18—H18C	109.5
C7—C6—C5	120.8 (2)	H18A—C18—H18C	109.5
C7—C6—H6	119.6	H18B—C18—H18C	109.5
C5—C6—H6	119.6	N2—C19—C20	122.16 (17)
C6—C7—C8	120.5 (2)	N2—C19—C1	115.24 (15)
C6—C7—H7	119.8	C20—C19—C1	122.56 (16)
C8—C7—H7	119.8	C21—C20—C19	119.26 (18)
C7—C8—C9	119.4 (2)	C21—C20—H20	120.4
C7—C8—H8	120.3	C19—C20—H20	120.4
C9—C8—H8	120.3	C22—C21—C20	118.92 (19)
C4—C9—C8	119.61 (19)	C22—C21—H21	120.5
C4—C9—C10	111.27 (16)	C20—C21—H21	120.5
C8—C9—C10	129.09 (18)	C21—C22—C23	118.6 (2)
C11—C10—C9	111.60 (14)	C21—C22—H22	120.7
C11—C10—C2	113.02 (14)	C23—C22—H22	120.7
C9—C10—C2	102.20 (14)	N2—C23—C22	123.90 (19)
C11—C10—H10	109.9	N2—C23—H23	118.1
C9—C10—H10	109.9	C22—C23—H23	118.1
C2—C10—H10	109.9

Cg4 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2i	0.87	2.53	3.345 (2)	157
C20—H20···N1	0.93	2.51	2.825 (3)	100
C14—H14···Cg4ii	0.93	2.74	3.611 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2i	0.87	2.53	3.345 (2)	157
C20—H20⋯N1	0.93	2.51	2.825 (3)	100
C14—H14⋯Cg4ii	0.93	2.74	3.611 (2)	153

Symmetry codes: (i) ; (ii) .