7-p-Tolyl-10,11-dihydro-benzo[h]furo[3,4-b]quinolin-8(7H)-one.

In the title compound, C(22)H(17)NO(2), the fused ring system is essentially planar (r.m.s. deviation = 0.021 Å) and the dihedral angle between the dihydro-pyridine and tolyl rings is 80.98 (11)°. In the crystal, the mol-ecules are linked into chains along the b axis by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds. Adjacent chains are linked by π-π inter-actions [centroid-centroid separation = 3.5748 (15) Å].

Related literature

For the biological activity 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 ▶). For a related structure, see: Shi & Ji (2009 ▶).

Experimental

Crystal data

C22H17NO2

M = 327.37

Monoclinic,

a = 10.6954 (16) Å

b = 13.0566 (18) Å

c = 12.183 (2) Å

β = 107.322 (3)°

V = 1624.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 223 K

0.60 × 0.34 × 0.30 mm

Data collection

Rigaku Mercury diffractometer

Absorption correction: multi-scan (Jacobson, 1998 ▶) T min = 0.770, T max = 0.975

15611 measured reflections

2978 independent reflections

2476 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.138

S = 1.18

2978 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.18 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/S160053681000591X/ci5030sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000591X/ci5030Isup2.hkl

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

C22H17NO2	F(000) = 688
Mr = 327.37	Dx = 1.339 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 5302 reflections
a = 10.6954 (16) Å	θ = 3.0–25.3°
b = 13.0566 (18) Å	µ = 0.09 mm−1
c = 12.183 (2) Å	T = 223 K
β = 107.322 (3)°	Block, colourless
V = 1624.1 (4) Å3	0.60 × 0.34 × 0.30 mm
Z = 4

Rigaku Mercury diffractometer	2978 independent reflections
Radiation source: fine-focus sealed tube	2476 reflections with I > 2σ(I)
graphite	Rint = 0.043
Detector resolution: 7.31 pixels mm-1	θmax = 25.4°, θmin = 3.1°
ω scans	h = −12→11
Absorption correction: multi-scan (Jacobson, 1998)	k = −15→12
Tmin = 0.770, Tmax = 0.975	l = −14→14
15611 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.0503P)2 + 0.6601P] where P = (Fo2 + 2Fc2)/3
2978 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	1.04628 (16)	0.87892 (12)	0.19046 (14)	0.0446 (4)
O2	1.02197 (17)	0.72658 (13)	0.26734 (16)	0.0520 (5)
N1	0.88595 (17)	1.05854 (13)	0.32900 (16)	0.0357 (5)
H1	0.8921	1.1200	0.3035	0.043*
C1	0.8218 (2)	1.04144 (15)	0.41266 (18)	0.0303 (5)
C2	0.8127 (2)	0.94420 (16)	0.45353 (18)	0.0321 (5)
C3	0.8734 (2)	0.84879 (15)	0.41573 (19)	0.0323 (5)
H3	0.9455	0.8252	0.4827	0.039*
C4	0.9332 (2)	0.88088 (16)	0.32405 (18)	0.0327 (5)
C5	0.9376 (2)	0.97791 (16)	0.28925 (19)	0.0330 (5)
C6	0.7450 (2)	0.93198 (18)	0.5358 (2)	0.0442 (6)
H6	0.7384	0.8661	0.5648	0.053*
C7	0.6888 (3)	1.01196 (18)	0.5748 (2)	0.0481 (7)
H7	0.6436	1.0004	0.6291	0.058*
C8	0.6977 (2)	1.11247 (17)	0.5345 (2)	0.0398 (6)
C9	0.6407 (3)	1.19767 (19)	0.5729 (2)	0.0518 (7)
H9	0.5941	1.1878	0.6264	0.062*
C10	0.6521 (3)	1.2934 (2)	0.5338 (3)	0.0570 (7)
H10	0.6140	1.3493	0.5605	0.068*
C11	0.7207 (3)	1.30888 (18)	0.4538 (2)	0.0515 (7)
H11	0.7296	1.3755	0.4279	0.062*
C12	0.7747 (2)	1.22844 (16)	0.4130 (2)	0.0413 (6)
H12	0.8189	1.2400	0.3580	0.050*
C13	0.7652 (2)	1.12779 (16)	0.45230 (19)	0.0330 (5)
C14	1.0009 (2)	0.81812 (18)	0.2636 (2)	0.0392 (6)
C15	1.0079 (2)	0.98353 (17)	0.2007 (2)	0.0410 (6)
H15A	0.9500	1.0088	0.1274	0.049*
H15B	1.0846	1.0284	0.2258	0.049*
C16	0.7751 (2)	0.76137 (15)	0.38090 (19)	0.0332 (5)
C17	0.7769 (2)	0.68286 (17)	0.4572 (2)	0.0436 (6)
H17	0.8420	0.6822	0.5288	0.052*
C18	0.6844 (3)	0.60477 (17)	0.4302 (2)	0.0463 (6)
H18	0.6875	0.5527	0.4842	0.056*
C19	0.5881 (2)	0.60229 (17)	0.3254 (2)	0.0395 (6)
C20	0.5876 (2)	0.68095 (17)	0.2488 (2)	0.0407 (6)
H20	0.5239	0.6809	0.1765	0.049*
C21	0.6785 (2)	0.75938 (17)	0.2760 (2)	0.0376 (5)
H21	0.6747	0.8121	0.2225	0.045*
C22	0.4884 (3)	0.51737 (19)	0.2961 (3)	0.0541 (7)
H22A	0.5015	0.4722	0.3618	0.081*
H22B	0.4985	0.4788	0.2312	0.081*
H22C	0.4010	0.5464	0.2763	0.081*

	U11	U22	U33	U12	U13	U23
O1	0.0519 (10)	0.0402 (9)	0.0490 (10)	0.0012 (7)	0.0264 (9)	−0.0075 (8)
O2	0.0626 (12)	0.0345 (10)	0.0664 (12)	0.0061 (8)	0.0305 (10)	−0.0097 (8)
N1	0.0415 (11)	0.0252 (9)	0.0463 (12)	0.0009 (8)	0.0222 (9)	0.0003 (8)
C1	0.0299 (11)	0.0312 (12)	0.0313 (12)	−0.0018 (9)	0.0113 (9)	−0.0033 (9)
C2	0.0358 (12)	0.0297 (12)	0.0310 (12)	−0.0014 (9)	0.0101 (10)	−0.0026 (9)
C3	0.0336 (12)	0.0266 (11)	0.0348 (12)	0.0022 (8)	0.0076 (10)	0.0009 (9)
C4	0.0306 (12)	0.0307 (12)	0.0357 (13)	−0.0018 (9)	0.0084 (10)	−0.0052 (9)
C5	0.0316 (12)	0.0320 (12)	0.0367 (13)	−0.0003 (9)	0.0119 (10)	−0.0032 (9)
C6	0.0605 (16)	0.0341 (13)	0.0444 (15)	−0.0012 (11)	0.0254 (12)	0.0034 (11)
C7	0.0632 (17)	0.0431 (14)	0.0503 (16)	0.0005 (12)	0.0355 (14)	−0.0009 (11)
C8	0.0432 (14)	0.0387 (13)	0.0404 (13)	0.0012 (10)	0.0171 (11)	−0.0048 (10)
C9	0.0601 (17)	0.0476 (16)	0.0573 (17)	0.0051 (12)	0.0321 (14)	−0.0091 (12)
C10	0.0614 (18)	0.0427 (16)	0.075 (2)	0.0090 (12)	0.0321 (16)	−0.0141 (13)
C11	0.0565 (16)	0.0305 (13)	0.0739 (19)	0.0039 (11)	0.0291 (14)	−0.0036 (12)
C12	0.0426 (13)	0.0309 (12)	0.0540 (16)	0.0001 (10)	0.0198 (12)	−0.0020 (11)
C13	0.0313 (12)	0.0312 (12)	0.0368 (13)	−0.0018 (9)	0.0108 (10)	−0.0039 (9)
C14	0.0393 (13)	0.0370 (14)	0.0409 (14)	−0.0001 (10)	0.0114 (11)	−0.0074 (10)
C15	0.0456 (14)	0.0368 (13)	0.0450 (15)	−0.0006 (10)	0.0201 (11)	−0.0048 (10)
C16	0.0366 (12)	0.0256 (11)	0.0379 (13)	0.0019 (9)	0.0118 (10)	−0.0013 (9)
C17	0.0518 (15)	0.0333 (13)	0.0394 (14)	−0.0025 (11)	0.0038 (11)	0.0035 (10)
C18	0.0605 (16)	0.0293 (12)	0.0495 (16)	−0.0050 (11)	0.0168 (13)	0.0046 (10)
C19	0.0372 (13)	0.0318 (12)	0.0523 (15)	−0.0022 (9)	0.0178 (11)	−0.0070 (10)
C20	0.0358 (13)	0.0414 (13)	0.0410 (14)	−0.0001 (10)	0.0056 (10)	−0.0050 (11)
C21	0.0418 (13)	0.0320 (12)	0.0383 (14)	0.0018 (10)	0.0109 (11)	0.0027 (10)
C22	0.0510 (15)	0.0437 (15)	0.071 (2)	−0.0125 (12)	0.0231 (14)	−0.0085 (13)

O1—C14	1.385 (3)	C9—H9	0.94
O1—C15	1.442 (3)	C10—C11	1.398 (4)
O2—C14	1.215 (3)	C10—H10	0.94
N1—C5	1.344 (3)	C11—C12	1.362 (3)
N1—C1	1.406 (3)	C11—H11	0.94
N1—H1	0.87	C12—C13	1.413 (3)
C1—C2	1.378 (3)	C12—H12	0.94
C1—C13	1.430 (3)	C15—H15A	0.98
C2—C6	1.409 (3)	C15—H15B	0.98
C2—C3	1.538 (3)	C16—C17	1.380 (3)
C3—C4	1.503 (3)	C16—C21	1.384 (3)
C3—C16	1.524 (3)	C17—C18	1.390 (3)
C3—H3	0.99	C17—H17	0.94
C4—C5	1.341 (3)	C18—C19	1.382 (3)
C4—C14	1.433 (3)	C18—H18	0.94
C5—C15	1.489 (3)	C19—C20	1.387 (3)
C6—C7	1.359 (3)	C19—C22	1.506 (3)
C6—H6	0.94	C20—C21	1.383 (3)
C7—C8	1.414 (3)	C20—H20	0.94
C7—H7	0.94	C21—H21	0.94
C8—C13	1.413 (3)	C22—H22A	0.97
C8—C9	1.413 (3)	C22—H22B	0.97
C9—C10	1.356 (4)	C22—H22C	0.97
C14—O1—C15	108.88 (16)	C11—C12—C13	120.8 (2)
C5—N1—C1	118.59 (18)	C11—C12—H12	119.6
C5—N1—H1	120.7	C13—C12—H12	119.6
C1—N1—H1	120.7	C8—C13—C12	118.4 (2)
C2—C1—N1	120.70 (18)	C8—C13—C1	119.01 (19)
C2—C1—C13	121.46 (19)	C12—C13—C1	122.6 (2)
N1—C1—C13	117.83 (18)	O2—C14—O1	119.4 (2)
C1—C2—C6	117.90 (19)	O2—C14—C4	131.3 (2)
C1—C2—C3	123.82 (18)	O1—C14—C4	109.28 (19)
C6—C2—C3	118.28 (19)	O1—C15—C5	103.55 (18)
C4—C3—C16	114.39 (18)	O1—C15—H15A	111.1
C4—C3—C2	107.95 (17)	C5—C15—H15A	111.1
C16—C3—C2	111.84 (17)	O1—C15—H15B	111.1
C4—C3—H3	107.5	C5—C15—H15B	111.1
C16—C3—H3	107.5	H15A—C15—H15B	109.0
C2—C3—H3	107.5	C17—C16—C21	117.7 (2)
C5—C4—C14	107.9 (2)	C17—C16—C3	119.9 (2)
C5—C4—C3	124.11 (19)	C21—C16—C3	122.32 (19)
C14—C4—C3	127.9 (2)	C16—C17—C18	121.3 (2)
C4—C5—N1	124.7 (2)	C16—C17—H17	119.4
C4—C5—C15	110.36 (19)	C18—C17—H17	119.4
N1—C5—C15	124.93 (19)	C19—C18—C17	121.2 (2)
C7—C6—C2	122.4 (2)	C19—C18—H18	119.4
C7—C6—H6	118.8	C17—C18—H18	119.4
C2—C6—H6	118.8	C18—C19—C20	117.2 (2)
C6—C7—C8	120.6 (2)	C18—C19—C22	121.2 (2)
C6—C7—H7	119.7	C20—C19—C22	121.7 (2)
C8—C7—H7	119.7	C21—C20—C19	121.7 (2)
C13—C8—C9	119.0 (2)	C21—C20—H20	119.1
C13—C8—C7	118.6 (2)	C19—C20—H20	119.1
C9—C8—C7	122.4 (2)	C20—C21—C16	120.9 (2)
C10—C9—C8	121.1 (2)	C20—C21—H21	119.6
C10—C9—H9	119.4	C16—C21—H21	119.6
C8—C9—H9	119.4	C19—C22—H22A	109.5
C9—C10—C11	119.9 (2)	C19—C22—H22B	109.5
C9—C10—H10	120.0	H22A—C22—H22B	109.5
C11—C10—H10	120.0	C19—C22—H22C	109.5
C12—C11—C10	120.7 (2)	H22A—C22—H22C	109.5
C12—C11—H11	119.6	H22B—C22—H22C	109.5
C10—C11—H11	119.6
C5—N1—C1—C2	0.4 (3)	C9—C8—C13—C1	−179.4 (2)
C5—N1—C1—C13	−178.79 (19)	C7—C8—C13—C1	0.1 (3)
N1—C1—C2—C6	−178.9 (2)	C11—C12—C13—C8	0.3 (4)
C13—C1—C2—C6	0.3 (3)	C11—C12—C13—C1	−179.3 (2)
N1—C1—C2—C3	1.9 (3)	C2—C1—C13—C8	−0.5 (3)
C13—C1—C2—C3	−178.92 (19)	N1—C1—C13—C8	178.7 (2)
C1—C2—C3—C4	−3.7 (3)	C2—C1—C13—C12	179.1 (2)
C6—C2—C3—C4	177.1 (2)	N1—C1—C13—C12	−1.7 (3)
C1—C2—C3—C16	−130.4 (2)	C15—O1—C14—O2	179.3 (2)
C6—C2—C3—C16	50.4 (3)	C15—O1—C14—C4	−0.6 (2)
C16—C3—C4—C5	128.9 (2)	C5—C4—C14—O2	179.8 (3)
C2—C3—C4—C5	3.7 (3)	C3—C4—C14—O2	3.2 (4)
C16—C3—C4—C14	−54.9 (3)	C5—C4—C14—O1	−0.3 (3)
C2—C3—C4—C14	179.9 (2)	C3—C4—C14—O1	−176.95 (19)
C14—C4—C5—N1	−178.8 (2)	C14—O1—C15—C5	1.1 (2)
C3—C4—C5—N1	−2.0 (4)	C4—C5—C15—O1	−1.3 (3)
C14—C4—C5—C15	1.0 (3)	N1—C5—C15—O1	178.54 (19)
C3—C4—C5—C15	177.8 (2)	C4—C3—C16—C17	137.1 (2)
C1—N1—C5—C4	−0.4 (3)	C2—C3—C16—C17	−99.8 (2)
C1—N1—C5—C15	179.8 (2)	C4—C3—C16—C21	−45.9 (3)
C1—C2—C6—C7	0.4 (4)	C2—C3—C16—C21	77.3 (3)
C3—C2—C6—C7	179.6 (2)	C21—C16—C17—C18	−0.5 (3)
C2—C6—C7—C8	−0.8 (4)	C3—C16—C17—C18	176.7 (2)
C6—C7—C8—C13	0.5 (4)	C16—C17—C18—C19	0.7 (4)
C6—C7—C8—C9	−180.0 (2)	C17—C18—C19—C20	−0.1 (4)
C13—C8—C9—C10	−1.3 (4)	C17—C18—C19—C22	179.7 (2)
C7—C8—C9—C10	179.2 (3)	C18—C19—C20—C21	−0.7 (3)
C8—C9—C10—C11	0.3 (4)	C22—C19—C20—C21	179.5 (2)
C9—C10—C11—C12	1.0 (4)	C19—C20—C21—C16	0.9 (3)
C10—C11—C12—C13	−1.3 (4)	C17—C16—C21—C20	−0.3 (3)
C9—C8—C13—C12	1.0 (3)	C3—C16—C21—C20	−177.4 (2)
C7—C8—C13—C12	−179.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.87	2.00	2.802 (2)	153
C12—H12···O1i	0.94	2.49	3.248 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.87	2.00	2.802 (2)	153
C12—H12⋯O1i	0.94	2.49	3.248 (3)	137

Symmetry code: (i) .