7-Methyl-9-p-tolyl-4,9-dihydro-furo[3,4-b]quinolin-1(3H)-one.

In the title compound, C(19)H(17)NO(2), the dihydro-pyridine ring adopts a flattened boat conformation while the furan-one ring is almost planar (r.m.s. deviation 0.018 Å). The mol-ecules are linked into chains along the b axis by N-H⋯O inter-molecular hydrogen bonds. In addition, C-H⋯π inter-actions involving the phenyl ring of the tolyl group as π acceptor are observed.

Related literature

For the biological activities of podophyllotoxin and its derivatives, see: Bosmans et al. (1989 ▶); Eycken et al. (1989 ▶); Hitosuyanagi et al. (1997 ▶, 1999 ▶); Lienard et al. (1991 ▶); Magedov et al. (2007 ▶); Poli & Giambastiani (2002 ▶); Tomioka et al. (1989 ▶, 1993 ▶); Tratrat et al. (2002 ▶).

Experimental

Crystal data

C19H17NO2

M = 291.34

Monoclinic,

a = 9.178 (2) Å

b = 11.457 (2) Å

c = 14.350 (4) Å

β = 103.124 (5)°

V = 1469.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 223 (2) K

0.60 × 0.48 × 0.45 mm

Data collection

Rigaku Mercury diffractometer

Absorption correction: multi-scan (Jacobson, 1998 ▶) T min = 0.756, T max = 0.962

13947 measured reflections

2675 independent reflections

2364 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.135

S = 1.16

2675 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku, 2000 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041457/ci2738sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041457/ci2738Isup2.hkl

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

C19H17NO2	F(000) = 616
Mr = 291.34	Dx = 1.317 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 4940 reflections
a = 9.178 (2) Å	θ = 3.3–25.3°
b = 11.457 (2) Å	µ = 0.09 mm−1
c = 14.350 (4) Å	T = 223 K
β = 103.124 (5)°	Block, colourless
V = 1469.5 (6) Å3	0.60 × 0.48 × 0.45 mm
Z = 4

Rigaku Mercury diffractometer	2675 independent reflections
Radiation source: fine-focus sealed tube	2364 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 7.31 pixels mm-1	θmax = 25.3°, θmin = 3.3°
ω scans	h = −11→11
Absorption correction: multi-scan (Jacobson, 1998)	k = −13→12
Tmin = 0.756, Tmax = 0.962	l = −17→17
13947 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.0497P)2 + 0.6176P] where P = (Fo2 + 2Fc2)/3
2675 reflections	(Δ/σ)max = 0.001
202 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.21 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
O1	−0.06775 (18)	0.28146 (14)	0.77022 (11)	0.0528 (4)
O2	−0.09551 (18)	0.13853 (14)	0.66103 (12)	0.0549 (5)
N1	0.14394 (19)	0.50270 (15)	0.68136 (12)	0.0396 (4)
H1	0.1588	0.5617	0.7205	0.048*
C1	0.1948 (2)	0.50585 (16)	0.59568 (14)	0.0343 (5)
C2	0.1821 (2)	0.40751 (17)	0.53741 (13)	0.0329 (5)
C3	0.1160 (2)	0.29193 (17)	0.56127 (14)	0.0342 (5)
H3	0.0327	0.2709	0.5069	0.041*
C4	0.0523 (2)	0.31008 (18)	0.64815 (14)	0.0366 (5)
C5	0.0727 (2)	0.40748 (18)	0.70132 (14)	0.0374 (5)
C6	0.2347 (2)	0.41594 (18)	0.45381 (14)	0.0382 (5)
H6	0.2259	0.3505	0.4134	0.046*
C7	0.2994 (2)	0.51643 (18)	0.42757 (15)	0.0400 (5)
C8	0.3088 (2)	0.61316 (18)	0.48745 (16)	0.0424 (5)
H8	0.3511	0.6827	0.4710	0.051*
C9	0.2572 (2)	0.60876 (18)	0.57031 (16)	0.0401 (5)
H9	0.2641	0.6750	0.6097	0.048*
C10	0.3607 (3)	0.5198 (2)	0.33889 (16)	0.0513 (6)
H10A	0.4686	0.5113	0.3565	0.077*
H10B	0.3352	0.5938	0.3064	0.077*
H10C	0.3178	0.4565	0.2966	0.077*
C11	−0.0401 (2)	0.2330 (2)	0.68790 (16)	0.0440 (5)
C12	0.0028 (3)	0.3941 (2)	0.78519 (16)	0.0479 (6)
H12A	0.0788	0.3961	0.8455	0.058*
H12B	−0.0709	0.4557	0.7860	0.058*
C13	0.2291 (2)	0.19179 (16)	0.57700 (13)	0.0319 (4)
C14	0.3781 (2)	0.20786 (18)	0.62247 (15)	0.0409 (5)
H14	0.4124	0.2829	0.6429	0.049*
C15	0.4770 (2)	0.11455 (19)	0.63815 (16)	0.0437 (5)
H15	0.5776	0.1279	0.6687	0.052*
C16	0.4311 (2)	0.00218 (17)	0.60993 (14)	0.0383 (5)
C17	0.2828 (2)	−0.01293 (18)	0.56396 (15)	0.0425 (5)
H17	0.2484	−0.0879	0.5433	0.051*
C18	0.1838 (2)	0.07991 (17)	0.54770 (15)	0.0394 (5)
H18	0.0837	0.0667	0.5161	0.047*
C19	0.5382 (3)	−0.0990 (2)	0.62813 (17)	0.0511 (6)
H19A	0.5792	−0.1118	0.5723	0.077*
H19B	0.4856	−0.1686	0.6408	0.077*
H19C	0.6187	−0.0820	0.6830	0.077*

	U11	U22	U33	U12	U13	U23
O1	0.0578 (10)	0.0565 (10)	0.0538 (10)	−0.0026 (8)	0.0326 (8)	0.0054 (8)
O2	0.0594 (10)	0.0468 (10)	0.0643 (11)	−0.0111 (8)	0.0259 (9)	0.0068 (8)
N1	0.0428 (10)	0.0394 (10)	0.0397 (10)	−0.0028 (8)	0.0160 (8)	−0.0071 (8)
C1	0.0297 (10)	0.0376 (11)	0.0370 (11)	0.0023 (8)	0.0104 (9)	0.0015 (9)
C2	0.0303 (10)	0.0354 (11)	0.0337 (10)	0.0012 (8)	0.0085 (8)	0.0035 (8)
C3	0.0328 (10)	0.0368 (11)	0.0343 (10)	−0.0020 (8)	0.0104 (8)	−0.0007 (8)
C4	0.0340 (10)	0.0408 (11)	0.0366 (11)	0.0017 (9)	0.0116 (9)	0.0047 (9)
C5	0.0313 (10)	0.0456 (12)	0.0370 (11)	0.0033 (9)	0.0111 (9)	0.0021 (9)
C6	0.0396 (11)	0.0398 (11)	0.0369 (11)	0.0026 (9)	0.0123 (9)	0.0015 (9)
C7	0.0359 (11)	0.0454 (12)	0.0400 (11)	0.0018 (9)	0.0114 (9)	0.0112 (9)
C8	0.0407 (12)	0.0365 (11)	0.0512 (13)	−0.0021 (9)	0.0129 (10)	0.0089 (10)
C9	0.0385 (11)	0.0340 (11)	0.0481 (12)	0.0002 (8)	0.0103 (10)	−0.0023 (9)
C10	0.0523 (14)	0.0589 (15)	0.0469 (13)	0.0007 (11)	0.0198 (11)	0.0130 (11)
C11	0.0407 (12)	0.0475 (13)	0.0478 (13)	0.0029 (10)	0.0184 (10)	0.0087 (10)
C12	0.0490 (13)	0.0545 (14)	0.0462 (13)	−0.0018 (10)	0.0232 (11)	−0.0011 (11)
C13	0.0363 (10)	0.0334 (10)	0.0283 (9)	−0.0030 (8)	0.0122 (8)	0.0000 (8)
C14	0.0415 (12)	0.0364 (11)	0.0433 (12)	−0.0054 (9)	0.0067 (9)	−0.0045 (9)
C15	0.0369 (11)	0.0479 (13)	0.0449 (12)	−0.0005 (9)	0.0065 (10)	−0.0002 (10)
C16	0.0470 (12)	0.0396 (12)	0.0316 (10)	0.0030 (9)	0.0158 (9)	0.0032 (8)
C17	0.0502 (13)	0.0344 (11)	0.0438 (12)	−0.0068 (9)	0.0123 (10)	−0.0035 (9)
C18	0.0368 (11)	0.0394 (11)	0.0416 (11)	−0.0067 (9)	0.0082 (9)	−0.0005 (9)
C19	0.0589 (14)	0.0472 (13)	0.0496 (13)	0.0105 (11)	0.0172 (11)	0.0042 (11)

O1—C11	1.380 (3)	C8—H8	0.94
O1—C12	1.438 (3)	C9—H9	0.94
O2—C11	1.220 (3)	C10—H10A	0.97
N1—C5	1.336 (3)	C10—H10B	0.97
N1—C1	1.411 (3)	C10—H10C	0.97
N1—H1	0.87	C12—H12A	0.98
C1—C2	1.392 (3)	C12—H12B	0.98
C1—C9	1.395 (3)	C13—C18	1.383 (3)
C2—C6	1.395 (3)	C13—C14	1.387 (3)
C2—C3	1.528 (3)	C14—C15	1.387 (3)
C3—C4	1.506 (3)	C14—H14	0.94
C3—C13	1.529 (3)	C15—C16	1.386 (3)
C3—H3	0.99	C15—H15	0.94
C4—C5	1.341 (3)	C16—C17	1.382 (3)
C4—C11	1.430 (3)	C16—C19	1.504 (3)
C5—C12	1.494 (3)	C17—C18	1.384 (3)
C6—C7	1.386 (3)	C17—H17	0.94
C6—H6	0.94	C18—H18	0.94
C7—C8	1.393 (3)	C19—H19A	0.97
C7—C10	1.504 (3)	C19—H19B	0.97
C8—C9	1.377 (3)	C19—H19C	0.97
C11—O1—C12	108.95 (16)	C7—C10—H10C	109.5
C5—N1—C1	118.85 (17)	H10A—C10—H10C	109.5
C5—N1—H1	120.6	H10B—C10—H10C	109.5
C1—N1—H1	120.6	O2—C11—O1	118.87 (19)
C2—C1—C9	120.68 (18)	O2—C11—C4	131.6 (2)
C2—C1—N1	120.25 (17)	O1—C11—C4	109.52 (19)
C9—C1—N1	119.06 (18)	O1—C12—C5	103.48 (17)
C1—C2—C6	117.57 (18)	O1—C12—H12A	111.1
C1—C2—C3	123.37 (17)	C5—C12—H12A	111.1
C6—C2—C3	119.06 (17)	O1—C12—H12B	111.1
C4—C3—C2	108.32 (16)	C5—C12—H12B	111.1
C4—C3—C13	111.04 (16)	H12A—C12—H12B	109.0
C2—C3—C13	113.10 (15)	C18—C13—C14	117.52 (18)
C4—C3—H3	108.1	C18—C13—C3	120.23 (17)
C2—C3—H3	108.1	C14—C13—C3	122.24 (17)
C13—C3—H3	108.1	C13—C14—C15	120.86 (19)
C5—C4—C11	107.79 (19)	C13—C14—H14	119.6
C5—C4—C3	123.77 (18)	C15—C14—H14	119.6
C11—C4—C3	128.43 (19)	C16—C15—C14	121.6 (2)
N1—C5—C4	124.70 (19)	C16—C15—H15	119.2
N1—C5—C12	125.25 (19)	C14—C15—H15	119.2
C4—C5—C12	110.05 (19)	C17—C16—C15	117.18 (19)
C7—C6—C2	122.99 (19)	C17—C16—C19	121.35 (19)
C7—C6—H6	118.5	C15—C16—C19	121.5 (2)
C2—C6—H6	118.5	C16—C17—C18	121.46 (19)
C6—C7—C8	117.62 (19)	C16—C17—H17	119.3
C6—C7—C10	121.1 (2)	C18—C17—H17	119.3
C8—C7—C10	121.2 (2)	C13—C18—C17	121.37 (19)
C9—C8—C7	121.21 (19)	C13—C18—H18	119.3
C9—C8—H8	119.4	C17—C18—H18	119.3
C7—C8—H8	119.4	C16—C19—H19A	109.5
C8—C9—C1	119.9 (2)	C16—C19—H19B	109.5
C8—C9—H9	120.0	H19A—C19—H19B	109.5
C1—C9—H9	120.0	C16—C19—H19C	109.5
C7—C10—H10A	109.5	H19A—C19—H19C	109.5
C7—C10—H10B	109.5	H19B—C19—H19C	109.5
H10A—C10—H10B	109.5
C5—N1—C1—C2	−5.5 (3)	C7—C8—C9—C1	0.3 (3)
C5—N1—C1—C9	174.32 (18)	C2—C1—C9—C8	−0.8 (3)
C9—C1—C2—C6	0.3 (3)	N1—C1—C9—C8	179.35 (18)
N1—C1—C2—C6	−179.82 (17)	C12—O1—C11—O2	−177.5 (2)
C9—C1—C2—C3	179.55 (17)	C12—O1—C11—C4	1.7 (2)
N1—C1—C2—C3	−0.6 (3)	C5—C4—C11—O2	174.9 (2)
C1—C2—C3—C4	7.1 (2)	C3—C4—C11—O2	−3.7 (4)
C6—C2—C3—C4	−173.67 (17)	C5—C4—C11—O1	−4.1 (2)
C1—C2—C3—C13	−116.4 (2)	C3—C4—C11—O1	177.31 (18)
C6—C2—C3—C13	62.8 (2)	C11—O1—C12—C5	1.1 (2)
C2—C3—C4—C5	−8.9 (3)	N1—C5—C12—O1	175.80 (19)
C13—C3—C4—C5	115.9 (2)	C4—C5—C12—O1	−3.7 (2)
C2—C3—C4—C11	169.54 (19)	C4—C3—C13—C18	93.7 (2)
C13—C3—C4—C11	−65.7 (3)	C2—C3—C13—C18	−144.25 (18)
C1—N1—C5—C4	4.0 (3)	C4—C3—C13—C14	−84.7 (2)
C1—N1—C5—C12	−175.41 (19)	C2—C3—C13—C14	37.3 (2)
C11—C4—C5—N1	−174.73 (19)	C18—C13—C14—C15	−0.4 (3)
C3—C4—C5—N1	4.0 (3)	C3—C13—C14—C15	178.10 (19)
C11—C4—C5—C12	4.8 (2)	C13—C14—C15—C16	−0.5 (3)
C3—C4—C5—C12	−176.55 (18)	C14—C15—C16—C17	1.0 (3)
C1—C2—C6—C7	0.7 (3)	C14—C15—C16—C19	−179.2 (2)
C3—C2—C6—C7	−178.55 (18)	C15—C16—C17—C18	−0.7 (3)
C2—C6—C7—C8	−1.2 (3)	C19—C16—C17—C18	179.6 (2)
C2—C6—C7—C10	177.29 (19)	C14—C13—C18—C17	0.7 (3)
C6—C7—C8—C9	0.7 (3)	C3—C13—C18—C17	−177.80 (18)
C10—C7—C8—C9	−177.79 (19)	C16—C17—C18—C13	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.87	2.11	2.862 (2)	144
C19—H19A···Cg1ii	0.97	2.69	3.645 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.87	2.11	2.862 (2)	144
C19—H19A⋯Cg1ii	0.97	2.69	3.645 (3)	167

Symmetry codes: (i) ; (ii) . Cg1 is centroid of the C13–C18 ring.