5-Phenyl-3,4,4a,5,6,12c-hexa-hydro-2H-benzo[f]pyrano[3,2-c]quinoline.

In the title compound, C(22)H(21)N, the pyridine ring adopts a distorted boat conformation, while the adjacent pyran ring adopts a chair conformation; the heterocyclic rings make a dihedral angle of 40.1 (2)° with each other.

Related literature

For the biological properties of pyran­oquinoline derivatives, see: Faber et al. (1984 ▶); Johnson et al. (1989 ▶); Schiemann et al. (2007 ▶); Yamada et al. (1992 ▶). Zhao & Teng (2008 ▶). For related structures, see: Ramesh et al. (2008 ▶); Zhao & Teng (2008 ▶); Bai et al. (2009 ▶).

Experimental

Crystal data

C22H21NO

M = 315.40

Monoclinic,

a = 8.1106 (2) Å

b = 10.9560 (2) Å

c = 18.5020 (3) Å

β = 93.552 (1)°

V = 1640.92 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.50 × 0.33 × 0.10 mm

Data collection

Bruker APEXII area-detector diffractometer

11135 measured reflections

2956 independent reflections

2303 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.140

S = 1.03

2956 reflections

221 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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/S1600536810020787/pv2287sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020787/pv2287Isup2.hkl

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

C22H21NO	F(000) = 672
Mr = 315.40	Dx = 1.277 Mg m−3
Monoclinic, P21/c	Melting point = 477–478 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.1106 (2) Å	Cell parameters from 3365 reflections
b = 10.9560 (2) Å	θ = 2.5–26.4°
c = 18.5020 (3) Å	µ = 0.08 mm−1
β = 93.552 (1)°	T = 296 K
V = 1640.92 (6) Å3	Block, colourless
Z = 4	0.50 × 0.33 × 0.10 mm

Bruker APEXII area-detector diffractometer	2303 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
graphite	θmax = 25.2°, θmin = 2.2°
φ & ω scans	h = −9→9
11135 measured reflections	k = −13→12
2956 independent reflections	l = −22→22

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0712P)2 + 0.4581P] where P = (Fo2 + 2Fc2)/3
2956 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.30 e Å−3
1 restraint	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
C4	0.3714 (2)	1.07478 (15)	0.36093 (9)	0.0408 (4)
N1	0.61481 (19)	0.95714 (14)	0.39789 (10)	0.0537 (4)
O1	0.18206 (15)	0.97459 (12)	0.43549 (7)	0.0562 (4)
C13	0.3017 (2)	1.18875 (15)	0.33707 (9)	0.0414 (4)
C5	0.5404 (2)	1.06466 (16)	0.37471 (10)	0.0439 (4)
C3	0.2648 (2)	0.96399 (16)	0.36947 (10)	0.0442 (4)
H3A	0.1808	0.9625	0.3291	0.053*
C8	0.4069 (2)	1.29013 (16)	0.32593 (9)	0.0452 (4)
C6	0.6433 (2)	1.16641 (18)	0.36261 (11)	0.0544 (5)
H6A	0.7571	1.1589	0.3711	0.065*
C1	0.5156 (2)	0.85413 (16)	0.42038 (10)	0.0470 (4)
H1A	0.4798	0.8705	0.4691	0.056*
C2	0.3629 (2)	0.84524 (16)	0.36796 (10)	0.0467 (4)
H2A	0.4012	0.8359	0.3191	0.056*
C7	0.5791 (2)	1.27409 (18)	0.33898 (11)	0.0529 (5)
H7A	0.6497	1.3390	0.3311	0.064*
C17	0.6191 (2)	0.73967 (16)	0.42288 (9)	0.0439 (4)
C10	0.1721 (3)	1.41656 (19)	0.29126 (12)	0.0623 (6)
H10A	0.1281	1.4914	0.2761	0.075*
C22	0.6980 (2)	0.69912 (17)	0.36296 (10)	0.0522 (5)
H22A	0.6887	0.7443	0.3203	0.063*
C9	0.3376 (3)	1.40304 (17)	0.30283 (10)	0.0552 (5)
H9A	0.4068	1.4690	0.2955	0.066*
C11	0.0673 (3)	1.31761 (19)	0.30220 (12)	0.0614 (5)
H11A	−0.0462	1.3270	0.2940	0.074*
C12	0.1299 (2)	1.20753 (17)	0.32474 (10)	0.0515 (5)
H12A	0.0579	1.1433	0.3322	0.062*
C16	0.2505 (3)	0.73714 (18)	0.38181 (12)	0.0603 (5)
H16A	0.1730	0.7260	0.3403	0.072*
H16B	0.3168	0.6637	0.3874	0.072*
C18	0.6379 (3)	0.6707 (2)	0.48508 (11)	0.0630 (6)
H18A	0.5869	0.6954	0.5263	0.076*
C21	0.7894 (3)	0.59365 (18)	0.36538 (11)	0.0581 (5)
H21A	0.8399	0.5676	0.3243	0.070*
C20	0.8067 (3)	0.52664 (18)	0.42770 (12)	0.0604 (5)
H20A	0.8693	0.4555	0.4293	0.073*
C15	0.1569 (3)	0.7550 (2)	0.44793 (14)	0.0697 (6)
H15A	0.2325	0.7529	0.4907	0.084*
H15B	0.0773	0.6896	0.4517	0.084*
C14	0.0693 (3)	0.8750 (2)	0.44381 (14)	0.0692 (6)
H14A	−0.0120	0.8742	0.4031	0.083*
H14B	0.0115	0.8871	0.4876	0.083*
C19	0.7316 (3)	0.5649 (2)	0.48709 (12)	0.0710 (6)
H19A	0.7431	0.5197	0.5296	0.085*
H1	0.7087	0.965	0.4204	0.087*

	U11	U22	U33	U12	U13	U23
C4	0.0409 (9)	0.0403 (9)	0.0416 (9)	−0.0009 (7)	0.0053 (7)	−0.0061 (7)
N1	0.0389 (8)	0.0454 (9)	0.0761 (11)	0.0008 (7)	−0.0021 (8)	−0.0027 (8)
O1	0.0504 (7)	0.0515 (8)	0.0685 (9)	−0.0046 (6)	0.0189 (6)	−0.0062 (6)
C13	0.0459 (9)	0.0410 (9)	0.0376 (9)	0.0006 (7)	0.0059 (7)	−0.0056 (7)
C5	0.0405 (9)	0.0423 (9)	0.0492 (10)	0.0001 (7)	0.0049 (7)	−0.0071 (8)
C3	0.0398 (9)	0.0440 (10)	0.0488 (10)	−0.0012 (7)	0.0026 (7)	−0.0022 (8)
C8	0.0532 (10)	0.0440 (10)	0.0390 (9)	−0.0010 (8)	0.0074 (8)	−0.0064 (7)
C6	0.0398 (9)	0.0557 (12)	0.0678 (13)	−0.0048 (9)	0.0050 (9)	−0.0073 (9)
C1	0.0455 (9)	0.0462 (10)	0.0496 (10)	0.0020 (8)	0.0038 (8)	−0.0062 (8)
C2	0.0476 (10)	0.0435 (10)	0.0489 (10)	0.0003 (8)	0.0019 (8)	−0.0057 (8)
C7	0.0537 (11)	0.0472 (11)	0.0589 (12)	−0.0109 (9)	0.0112 (9)	−0.0048 (9)
C17	0.0430 (9)	0.0433 (10)	0.0454 (10)	0.0001 (7)	0.0020 (7)	−0.0028 (8)
C10	0.0745 (14)	0.0462 (11)	0.0665 (13)	0.0146 (10)	0.0071 (11)	0.0003 (9)
C22	0.0618 (11)	0.0503 (11)	0.0454 (11)	0.0115 (9)	0.0096 (9)	0.0059 (8)
C9	0.0721 (13)	0.0404 (10)	0.0540 (11)	−0.0021 (9)	0.0107 (10)	−0.0030 (8)
C11	0.0552 (11)	0.0587 (13)	0.0703 (14)	0.0132 (10)	0.0037 (10)	−0.0008 (10)
C12	0.0486 (10)	0.0484 (11)	0.0578 (12)	0.0031 (8)	0.0059 (8)	−0.0018 (9)
C16	0.0605 (12)	0.0451 (11)	0.0738 (14)	−0.0038 (9)	−0.0096 (10)	0.0002 (10)
C18	0.0726 (13)	0.0731 (14)	0.0438 (11)	0.0105 (11)	0.0073 (9)	0.0028 (10)
C21	0.0641 (12)	0.0514 (11)	0.0597 (12)	0.0096 (10)	0.0108 (10)	−0.0051 (9)
C20	0.0629 (12)	0.0432 (11)	0.0742 (14)	0.0053 (9)	−0.0028 (10)	0.0043 (10)
C15	0.0634 (13)	0.0569 (13)	0.0885 (17)	−0.0110 (10)	0.0021 (12)	0.0077 (12)
C14	0.0556 (12)	0.0630 (13)	0.0909 (17)	−0.0118 (10)	0.0195 (11)	0.0038 (12)
C19	0.0862 (16)	0.0659 (14)	0.0603 (14)	0.0146 (12)	−0.0002 (12)	0.0210 (11)

C4—C5	1.383 (2)	C10—C9	1.355 (3)
C4—C13	1.429 (2)	C10—C11	1.400 (3)
C4—C3	1.504 (2)	C10—H10A	0.9300
N1—C5	1.380 (2)	C22—C21	1.372 (3)
N1—C1	1.461 (2)	C22—H22A	0.9300
N1—H1	0.850	C9—H9A	0.9300
O1—C3	1.434 (2)	C11—C12	1.364 (3)
O1—C14	1.438 (2)	C11—H11A	0.9300
C13—C12	1.413 (2)	C12—H12A	0.9300
C13—C8	1.423 (2)	C16—C15	1.492 (3)
C5—C6	1.418 (3)	C16—H16A	0.9700
C3—C2	1.526 (2)	C16—H16B	0.9700
C3—H3A	0.9800	C18—C19	1.385 (3)
C8—C9	1.414 (3)	C18—H18A	0.9300
C8—C7	1.414 (3)	C21—C20	1.367 (3)
C6—C7	1.351 (3)	C21—H21A	0.9300
C6—H6A	0.9300	C20—C19	1.355 (3)
C1—C17	1.508 (2)	C20—H20A	0.9300
C1—C2	1.529 (3)	C15—C14	1.494 (3)
C1—H1A	0.9800	C15—H15A	0.9700
C2—C16	1.526 (3)	C15—H15B	0.9700
C2—H2A	0.9800	C14—H14A	0.9700
C7—H7A	0.9300	C14—H14B	0.9700
C17—C18	1.378 (3)	C19—H19A	0.9300
C17—C22	1.387 (2)
C5—C4—C13	119.71 (15)	C9—C10—H10A	120.1
C5—C4—C3	119.05 (15)	C11—C10—H10A	120.1
C13—C4—C3	121.22 (15)	C21—C22—C17	121.24 (18)
C5—N1—C1	120.68 (14)	C21—C22—H22A	119.4
C5—N1—H1	115.1	C17—C22—H22A	119.4
C1—N1—H1	115.7	C10—C9—C8	120.97 (19)
C3—O1—C14	111.34 (15)	C10—C9—H9A	119.5
C12—C13—C8	117.18 (16)	C8—C9—H9A	119.5
C12—C13—C4	122.99 (16)	C12—C11—C10	120.76 (19)
C8—C13—C4	119.82 (15)	C12—C11—H11A	119.6
N1—C5—C4	122.34 (16)	C10—C11—H11A	119.6
N1—C5—C6	118.03 (15)	C11—C12—C13	121.52 (19)
C4—C5—C6	119.60 (16)	C11—C12—H12A	119.2
O1—C3—C4	109.05 (13)	C13—C12—H12A	119.2
O1—C3—C2	110.88 (14)	C15—C16—C2	112.03 (17)
C4—C3—C2	112.49 (14)	C15—C16—H16A	109.2
O1—C3—H3A	108.1	C2—C16—H16A	109.2
C4—C3—H3A	108.1	C15—C16—H16B	109.2
C2—C3—H3A	108.1	C2—C16—H16B	109.2
C9—C8—C7	122.01 (17)	H16A—C16—H16B	107.9
C9—C8—C13	119.76 (17)	C17—C18—C19	120.90 (19)
C7—C8—C13	118.23 (16)	C17—C18—H18A	119.6
C7—C6—C5	121.22 (17)	C19—C18—H18A	119.6
C7—C6—H6A	119.4	C20—C21—C22	120.45 (19)
C5—C6—H6A	119.4	C20—C21—H21A	119.8
N1—C1—C17	109.61 (14)	C22—C21—H21A	119.8
N1—C1—C2	107.90 (15)	C19—C20—C21	119.34 (19)
C17—C1—C2	113.22 (14)	C19—C20—H20A	120.3
N1—C1—H1A	108.7	C21—C20—H20A	120.3
C17—C1—H1A	108.7	C16—C15—C14	109.77 (19)
C2—C1—H1A	108.7	C16—C15—H15A	109.7
C16—C2—C3	109.97 (15)	C14—C15—H15A	109.7
C16—C2—C1	114.33 (16)	C16—C15—H15B	109.7
C3—C2—C1	109.69 (14)	C14—C15—H15B	109.7
C16—C2—H2A	107.5	H15A—C15—H15B	108.2
C3—C2—H2A	107.5	O1—C14—C15	111.70 (17)
C1—C2—H2A	107.5	O1—C14—H14A	109.3
C6—C7—C8	121.39 (17)	C15—C14—H14A	109.3
C6—C7—H7A	119.3	O1—C14—H14B	109.3
C8—C7—H7A	119.3	C15—C14—H14B	109.3
C18—C17—C22	117.36 (17)	H14A—C14—H14B	107.9
C18—C17—C1	120.95 (17)	C20—C19—C18	120.71 (19)
C22—C17—C1	121.68 (16)	C20—C19—H19A	119.6
C9—C10—C11	119.80 (19)	C18—C19—H19A	119.6
C5—C4—C13—C12	−177.36 (16)	N1—C1—C2—C3	−59.10 (19)
C3—C4—C13—C12	4.4 (3)	C17—C1—C2—C3	179.41 (14)
C5—C4—C13—C8	1.5 (2)	C5—C6—C7—C8	0.5 (3)
C3—C4—C13—C8	−176.73 (15)	C9—C8—C7—C6	178.50 (18)
C1—N1—C5—C4	−10.1 (3)	C13—C8—C7—C6	−1.1 (3)
C1—N1—C5—C6	171.94 (17)	N1—C1—C17—C18	124.28 (19)
C13—C4—C5—N1	179.96 (16)	C2—C1—C17—C18	−115.2 (2)
C3—C4—C5—N1	−1.7 (3)	N1—C1—C17—C22	−56.2 (2)
C13—C4—C5—C6	−2.2 (3)	C2—C1—C17—C22	64.3 (2)
C3—C4—C5—C6	176.16 (16)	C18—C17—C22—C21	0.8 (3)
C14—O1—C3—C4	175.92 (15)	C1—C17—C22—C21	−178.78 (17)
C14—O1—C3—C2	−59.69 (19)	C11—C10—C9—C8	0.0 (3)
C5—C4—C3—O1	104.13 (17)	C7—C8—C9—C10	−179.42 (18)
C13—C4—C3—O1	−77.58 (19)	C13—C8—C9—C10	0.2 (3)
C5—C4—C3—C2	−19.3 (2)	C9—C10—C11—C12	0.3 (3)
C13—C4—C3—C2	158.98 (15)	C10—C11—C12—C13	−0.7 (3)
C12—C13—C8—C9	−0.6 (2)	C8—C13—C12—C11	0.8 (3)
C4—C13—C8—C9	−179.55 (15)	C4—C13—C12—C11	179.77 (17)
C12—C13—C8—C7	179.06 (16)	C3—C2—C16—C15	−51.1 (2)
C4—C13—C8—C7	0.1 (2)	C1—C2—C16—C15	72.8 (2)
N1—C5—C6—C7	179.13 (18)	C22—C17—C18—C19	−0.2 (3)
C4—C5—C6—C7	1.2 (3)	C1—C17—C18—C19	179.35 (19)
C5—N1—C1—C17	164.33 (16)	C17—C22—C21—C20	−0.9 (3)
C5—N1—C1—C2	40.6 (2)	C22—C21—C20—C19	0.5 (3)
O1—C3—C2—C16	53.87 (19)	C2—C16—C15—C14	52.5 (2)
C4—C3—C2—C16	176.28 (15)	C3—O1—C14—C15	61.8 (2)
O1—C3—C2—C1	−72.68 (18)	C16—C15—C14—O1	−57.3 (3)
C4—C3—C2—C1	49.7 (2)	C21—C20—C19—C18	0.1 (3)
N1—C1—C2—C16	176.86 (15)	C17—C18—C19—C20	−0.2 (4)
C17—C1—C2—C16	55.4 (2)