Methyl 4-phenyl-1,2,3,3a,4,4a,5,12c-octa-hydronaphtho[1',2':3,2]furo[5,4-b]pyrrolizine-4a-carboxyl-ate.

In the title compound, C(26)H(25)NO(3), both pyrrolidine rings adopt envelope conformations, whereas the dihydro-pyran ring adopts a half-chair conformation. The phenyl ring is oriented at an angle of 27.9 (1)° with respect to the naphthalene ring system. An intra-molecular C-H⋯O hydrogen bond is observed. The crystal packing is stabilized by weak inter-molecular C-H⋯π inter-actions.

Related literature

For general background to pyrrolizine derivatives, see: Barsoum & Nawar (2003 ▶); Abbas et al. (2010 ▶); Anderson & Corey (1977 ▶); Makoni & Sugden (1980 ▶); Laufer et al. (1997 ▶). For a related structure, see: Nirmala et al. (2009 ▶). For ring-puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C26H25NO3

M = 399.47

Orthorhombic,

a = 15.0117 (12) Å

b = 13.3421 (11) Å

c = 20.0242 (16) Å

V = 4010.6 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 292 K

0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

43738 measured reflections

4779 independent reflections

3892 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.134

S = 1.04

4779 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.14 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: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017307/ci5092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017307/ci5092Isup2.hkl

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

C26H25NO3	F(000) = 1696
Mr = 399.47	Dx = 1.323 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 31182 reflections
a = 15.0117 (12) Å	θ = 2.1–27.3°
b = 13.3421 (11) Å	µ = 0.09 mm−1
c = 20.0242 (16) Å	T = 292 K
V = 4010.6 (6) Å3	Block, colourless
Z = 8	0.24 × 0.22 × 0.20 mm

Bruker SMART APEX CCD area-detector diffractometer	3892 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 28.0°, θmin = 2.0°
ω scans	h = −19→19
43738 measured reflections	k = −17→17
4779 independent reflections	l = −26→26

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) = 0.134	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0727P)2 + 0.9686P] where P = (Fo2 + 2Fc2)/3
4779 reflections	(Δ/σ)max = 0.001
272 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.14 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	0.10550 (8)	−0.01484 (8)	0.07769 (6)	0.0520 (3)
O2	0.00482 (7)	0.17668 (10)	0.09040 (6)	0.0580 (3)
O3	0.10217 (7)	0.27234 (10)	0.14444 (6)	0.0557 (3)
C1	0.23953 (8)	0.13141 (9)	0.11484 (6)	0.0320 (3)
H1	0.2427	0.1849	0.1483	0.038*
C11	0.15871 (10)	−0.02986 (10)	0.13242 (7)	0.0416 (3)
C10	0.13883 (12)	−0.11691 (11)	0.17021 (9)	0.0519 (4)
H10	0.0920	−0.1583	0.1574	0.062*
C9	0.18806 (12)	−0.13999 (11)	0.22501 (8)	0.0498 (4)
H9	0.1741	−0.1971	0.2495	0.060*
C8	0.26021 (10)	−0.07888 (10)	0.24562 (7)	0.0403 (3)
C7	0.31301 (12)	−0.10157 (12)	0.30224 (7)	0.0488 (4)
H7	0.3009	−0.1592	0.3267	0.059*
C6	0.38112 (12)	−0.04072 (13)	0.32157 (8)	0.0524 (4)
H6	0.4144	−0.0562	0.3594	0.063*
C5	0.40078 (11)	0.04538 (12)	0.28425 (8)	0.0477 (4)
H5	0.4479	0.0864	0.2971	0.057*
C4	0.35132 (10)	0.06990 (10)	0.22891 (7)	0.0400 (3)
H4	0.3655	0.1272	0.2047	0.048*
C3	0.27917 (9)	0.00946 (9)	0.20814 (6)	0.0346 (3)
C2	0.22530 (9)	0.03416 (9)	0.15139 (6)	0.0348 (3)
C13	0.16187 (8)	0.15725 (9)	0.06619 (6)	0.0330 (3)
C12	0.13359 (10)	0.06083 (11)	0.03088 (7)	0.0415 (3)
H12A	0.0850	0.0755	0.0004	0.050*
H12B	0.1831	0.0354	0.0048	0.050*
N1	0.32208 (7)	0.13550 (8)	0.07478 (5)	0.0347 (3)
C18	0.36312 (10)	0.04152 (11)	0.05115 (8)	0.0438 (3)
H18A	0.3189	−0.0111	0.0471	0.053*
H18B	0.4095	0.0195	0.0815	0.053*
C17	0.40179 (10)	0.06837 (12)	−0.01673 (8)	0.0450 (3)
H17A	0.4072	0.0095	−0.0449	0.054*
H17B	0.4598	0.0996	−0.0122	0.054*
C16	0.33354 (10)	0.14184 (12)	−0.04488 (7)	0.0431 (3)
H16A	0.2827	0.1069	−0.0637	0.052*
H16B	0.3598	0.1844	−0.0789	0.052*
C15	0.30691 (9)	0.20250 (10)	0.01671 (6)	0.0349 (3)
H15	0.3468	0.2604	0.0205	0.042*
C14	0.20917 (8)	0.23942 (10)	0.02349 (6)	0.0327 (3)
H14	0.2124	0.2983	0.0527	0.039*
C25	0.08026 (9)	0.20086 (10)	0.10127 (6)	0.0362 (3)
C26	0.02975 (12)	0.32140 (15)	0.17845 (10)	0.0615 (5)
H26A	−0.0140	0.3423	0.1464	0.092*
H26B	0.0519	0.3789	0.2020	0.092*
H26C	0.0031	0.2757	0.2096	0.092*
C19	0.16797 (9)	0.27750 (9)	−0.04106 (6)	0.0336 (3)
C24	0.07883 (9)	0.26452 (10)	−0.05833 (7)	0.0398 (3)
H24	0.0424	0.2252	−0.0314	0.048*
C23	0.04346 (11)	0.30931 (11)	−0.11511 (8)	0.0469 (4)
H23	−0.0165	0.3008	−0.1253	0.056*
C22	0.09672 (12)	0.36633 (12)	−0.15645 (8)	0.0505 (4)
H22	0.0733	0.3952	−0.1949	0.061*
C21	0.18522 (11)	0.38012 (12)	−0.14008 (8)	0.0493 (4)
H21	0.2215	0.4187	−0.1676	0.059*
C20	0.22020 (10)	0.33690 (11)	−0.08297 (7)	0.0415 (3)
H20	0.2797	0.3477	−0.0723	0.050*

	U11	U22	U33	U12	U13	U23
O1	0.0578 (7)	0.0420 (5)	0.0561 (6)	−0.0168 (5)	−0.0144 (5)	0.0024 (5)
O2	0.0359 (6)	0.0730 (8)	0.0650 (7)	−0.0104 (5)	0.0103 (5)	−0.0186 (6)
O3	0.0384 (5)	0.0666 (7)	0.0622 (7)	0.0043 (5)	0.0008 (5)	−0.0281 (6)
C1	0.0346 (6)	0.0304 (6)	0.0311 (6)	−0.0025 (5)	−0.0002 (5)	0.0001 (5)
C11	0.0473 (8)	0.0343 (7)	0.0432 (8)	−0.0044 (6)	−0.0007 (6)	−0.0009 (6)
C10	0.0575 (9)	0.0356 (7)	0.0628 (10)	−0.0137 (7)	0.0014 (8)	0.0002 (7)
C9	0.0633 (10)	0.0324 (7)	0.0539 (9)	−0.0039 (6)	0.0109 (8)	0.0079 (6)
C8	0.0518 (8)	0.0320 (6)	0.0369 (7)	0.0056 (6)	0.0111 (6)	0.0022 (5)
C7	0.0648 (10)	0.0430 (8)	0.0387 (7)	0.0134 (7)	0.0112 (7)	0.0103 (6)
C6	0.0618 (10)	0.0594 (10)	0.0359 (7)	0.0139 (8)	−0.0014 (7)	0.0064 (7)
C5	0.0513 (9)	0.0525 (8)	0.0394 (7)	0.0014 (7)	−0.0040 (6)	−0.0010 (6)
C4	0.0466 (7)	0.0383 (7)	0.0351 (7)	−0.0005 (6)	0.0011 (6)	0.0016 (5)
C3	0.0422 (7)	0.0312 (6)	0.0304 (6)	0.0028 (5)	0.0058 (5)	0.0002 (5)
C2	0.0402 (7)	0.0302 (6)	0.0339 (6)	−0.0019 (5)	0.0032 (5)	−0.0004 (5)
C13	0.0328 (6)	0.0348 (6)	0.0315 (6)	−0.0014 (5)	0.0021 (5)	0.0005 (5)
C12	0.0456 (8)	0.0404 (7)	0.0386 (7)	−0.0044 (6)	−0.0037 (6)	−0.0041 (6)
N1	0.0342 (6)	0.0349 (5)	0.0349 (6)	0.0015 (4)	0.0014 (4)	0.0029 (4)
C18	0.0453 (8)	0.0398 (7)	0.0463 (8)	0.0088 (6)	0.0031 (6)	0.0005 (6)
C17	0.0402 (7)	0.0503 (8)	0.0444 (8)	0.0085 (6)	0.0025 (6)	−0.0061 (6)
C16	0.0393 (7)	0.0547 (8)	0.0352 (7)	0.0064 (6)	0.0037 (6)	−0.0012 (6)
C15	0.0321 (6)	0.0379 (7)	0.0347 (6)	−0.0006 (5)	0.0012 (5)	0.0031 (5)
C14	0.0322 (6)	0.0326 (6)	0.0334 (6)	−0.0015 (5)	0.0018 (5)	0.0005 (5)
C25	0.0346 (7)	0.0416 (7)	0.0322 (6)	−0.0029 (5)	0.0038 (5)	0.0030 (5)
C26	0.0476 (9)	0.0748 (12)	0.0619 (10)	0.0107 (8)	0.0039 (8)	−0.0265 (9)
C19	0.0362 (7)	0.0320 (6)	0.0326 (6)	0.0033 (5)	0.0018 (5)	−0.0001 (5)
C24	0.0375 (7)	0.0402 (7)	0.0418 (7)	−0.0004 (5)	0.0008 (6)	0.0021 (6)
C23	0.0458 (8)	0.0465 (8)	0.0483 (8)	0.0014 (6)	−0.0112 (6)	−0.0031 (6)
C22	0.0647 (10)	0.0488 (8)	0.0379 (7)	0.0054 (7)	−0.0101 (7)	0.0055 (6)
C21	0.0567 (9)	0.0477 (8)	0.0436 (8)	0.0007 (7)	0.0060 (7)	0.0121 (6)
C20	0.0390 (7)	0.0426 (7)	0.0429 (7)	−0.0002 (6)	0.0021 (6)	0.0055 (6)

O1—C11	1.3708 (18)	C12—H12B	0.97
O1—C12	1.4408 (18)	N1—C18	1.4751 (18)
O2—C25	1.1974 (17)	N1—C15	1.4842 (16)
O3—C25	1.3285 (17)	C18—C17	1.521 (2)
O3—C26	1.4402 (18)	C18—H18A	0.97
C1—N1	1.4771 (16)	C18—H18B	0.97
C1—C2	1.5049 (17)	C17—C16	1.526 (2)
C1—C13	1.5578 (18)	C17—H17A	0.97
C1—H1	0.98	C17—H17B	0.97
C11—C2	1.3686 (19)	C16—C15	1.5283 (19)
C11—C10	1.418 (2)	C16—H16A	0.97
C10—C9	1.358 (2)	C16—H16B	0.97
C10—H10	0.93	C15—C14	1.5538 (18)
C9—C8	1.417 (2)	C15—H15	0.98
C9—H9	0.93	C14—C19	1.5202 (17)
C8—C7	1.416 (2)	C14—H14	0.98
C8—C3	1.4261 (18)	C26—H26A	0.96
C7—C6	1.362 (3)	C26—H26B	0.96
C7—H7	0.93	C26—H26C	0.96
C6—C5	1.402 (2)	C19—C24	1.3931 (19)
C6—H6	0.93	C19—C20	1.3953 (19)
C5—C4	1.373 (2)	C24—C23	1.390 (2)
C5—H5	0.93	C24—H24	0.93
C4—C3	1.413 (2)	C23—C22	1.380 (2)
C4—H4	0.93	C23—H23	0.93
C3—C2	1.4331 (19)	C22—C21	1.381 (2)
C13—C25	1.5274 (18)	C22—H22	0.93
C13—C12	1.5281 (18)	C21—C20	1.384 (2)
C13—C14	1.5612 (17)	C21—H21	0.93
C12—H12A	0.97	C20—H20	0.93
C11—O1—C12	116.86 (11)	C17—C18—H18A	110.9
C25—O3—C26	116.55 (12)	N1—C18—H18B	110.9
N1—C1—C2	114.52 (10)	C17—C18—H18B	110.9
N1—C1—C13	106.26 (10)	H18A—C18—H18B	108.9
C2—C1—C13	112.87 (10)	C18—C17—C16	103.01 (11)
N1—C1—H1	107.6	C18—C17—H17A	111.2
C2—C1—H1	107.6	C16—C17—H17A	111.2
C13—C1—H1	107.6	C18—C17—H17B	111.2
C2—C11—O1	123.80 (13)	C16—C17—H17B	111.2
C2—C11—C10	121.12 (14)	H17A—C17—H17B	109.1
O1—C11—C10	115.07 (13)	C17—C16—C15	102.57 (11)
C9—C10—C11	120.15 (15)	C17—C16—H16A	111.3
C9—C10—H10	119.9	C15—C16—H16A	111.3
C11—C10—H10	119.9	C17—C16—H16B	111.3
C10—C9—C8	121.38 (13)	C15—C16—H16B	111.3
C10—C9—H9	119.3	H16A—C16—H16B	109.2
C8—C9—H9	119.3	N1—C15—C16	105.85 (11)
C7—C8—C9	122.55 (13)	N1—C15—C14	105.50 (10)
C7—C8—C3	119.10 (14)	C16—C15—C14	119.04 (11)
C9—C8—C3	118.34 (13)	N1—C15—H15	108.7
C6—C7—C8	121.36 (14)	C16—C15—H15	108.7
C6—C7—H7	119.3	C14—C15—H15	108.7
C8—C7—H7	119.3	C19—C14—C15	114.57 (10)
C7—C6—C5	119.67 (15)	C19—C14—C13	121.02 (10)
C7—C6—H6	120.2	C15—C14—C13	104.76 (10)
C5—C6—H6	120.2	C19—C14—H14	105.0
C4—C5—C6	120.76 (15)	C15—C14—H14	105.0
C4—C5—H5	119.6	C13—C14—H14	105.0
C6—C5—H5	119.6	O2—C25—O3	123.08 (13)
C5—C4—C3	121.07 (13)	O2—C25—C13	124.91 (13)
C5—C4—H4	119.5	O3—C25—C13	111.97 (11)
C3—C4—H4	119.5	O3—C26—H26A	109.5
C4—C3—C8	118.02 (12)	O3—C26—H26B	109.5
C4—C3—C2	122.33 (12)	H26A—C26—H26B	109.5
C8—C3—C2	119.66 (13)	O3—C26—H26C	109.5
C11—C2—C3	119.25 (12)	H26A—C26—H26C	109.5
C11—C2—C1	120.45 (12)	H26B—C26—H26C	109.5
C3—C2—C1	120.25 (12)	C24—C19—C20	117.45 (12)
C25—C13—C12	108.10 (11)	C24—C19—C14	124.08 (12)
C25—C13—C1	113.39 (10)	C20—C19—C14	118.20 (12)
C12—C13—C1	108.12 (10)	C23—C24—C19	121.11 (13)
C25—C13—C14	110.43 (10)	C23—C24—H24	119.4
C12—C13—C14	117.65 (11)	C19—C24—H24	119.4
C1—C13—C14	99.06 (9)	C22—C23—C24	120.44 (14)
O1—C12—C13	111.73 (11)	C22—C23—H23	119.8
O1—C12—H12A	109.3	C24—C23—H23	119.8
C13—C12—H12A	109.3	C23—C22—C21	119.25 (14)
O1—C12—H12B	109.3	C23—C22—H22	120.4
C13—C12—H12B	109.3	C21—C22—H22	120.4
H12A—C12—H12B	107.9	C22—C21—C20	120.38 (14)
C18—N1—C1	119.55 (11)	C22—C21—H21	119.8
C18—N1—C15	108.94 (10)	C20—C21—H21	119.8
C1—N1—C15	108.61 (10)	C21—C20—C19	121.36 (14)
N1—C18—C17	104.24 (11)	C21—C20—H20	119.3
N1—C18—H18A	110.9	C19—C20—H20	119.3
C12—O1—C11—C2	13.1 (2)	C2—C1—N1—C15	149.91 (11)
C12—O1—C11—C10	−168.32 (13)	C13—C1—N1—C15	24.60 (13)
C2—C11—C10—C9	−2.3 (3)	C1—N1—C18—C17	145.27 (12)
O1—C11—C10—C9	179.13 (15)	C15—N1—C18—C17	19.65 (15)
C11—C10—C9—C8	−0.4 (3)	N1—C18—C17—C16	−36.07 (15)
C10—C9—C8—C7	−179.52 (15)	C18—C17—C16—C15	38.40 (15)
C10—C9—C8—C3	1.3 (2)	C18—N1—C15—C16	4.57 (14)
C9—C8—C7—C6	−178.96 (15)	C1—N1—C15—C16	−127.17 (11)
C3—C8—C7—C6	0.2 (2)	C18—N1—C15—C14	131.61 (11)
C8—C7—C6—C5	−1.1 (2)	C1—N1—C15—C14	−0.13 (13)
C7—C6—C5—C4	0.9 (2)	C17—C16—C15—N1	−26.71 (14)
C6—C5—C4—C3	0.2 (2)	C17—C16—C15—C14	−145.10 (12)
C5—C4—C3—C8	−1.2 (2)	N1—C15—C14—C19	−159.08 (10)
C5—C4—C3—C2	178.77 (14)	C16—C15—C14—C19	−40.51 (16)
C7—C8—C3—C4	0.96 (19)	N1—C15—C14—C13	−24.14 (13)
C9—C8—C3—C4	−179.87 (13)	C16—C15—C14—C13	94.43 (13)
C7—C8—C3—C2	−178.97 (12)	C25—C13—C14—C19	−72.42 (14)
C9—C8—C3—C2	0.20 (19)	C12—C13—C14—C19	52.29 (16)
O1—C11—C2—C3	−177.76 (13)	C1—C13—C14—C19	168.34 (11)
C10—C11—C2—C3	3.8 (2)	C25—C13—C14—C15	156.27 (11)
O1—C11—C2—C1	4.7 (2)	C12—C13—C14—C15	−79.02 (14)
C10—C11—C2—C1	−173.79 (13)	C1—C13—C14—C15	37.03 (12)
C4—C3—C2—C11	177.36 (13)	C26—O3—C25—O2	−0.3 (2)
C8—C3—C2—C11	−2.7 (2)	C26—O3—C25—C13	177.64 (14)
C4—C3—C2—C1	−5.09 (19)	C12—C13—C25—O2	−15.40 (19)
C8—C3—C2—C1	174.83 (11)	C1—C13—C25—O2	−135.26 (15)
N1—C1—C2—C11	−110.51 (14)	C14—C13—C25—O2	114.60 (16)
C13—C1—C2—C11	11.26 (18)	C12—C13—C25—O3	166.74 (12)
N1—C1—C2—C3	71.97 (15)	C1—C13—C25—O3	46.88 (15)
C13—C1—C2—C3	−166.26 (11)	C14—C13—C25—O3	−63.26 (14)
N1—C1—C13—C25	−154.82 (10)	C15—C14—C19—C24	144.48 (13)
C2—C1—C13—C25	78.87 (13)	C13—C14—C19—C24	17.48 (19)
N1—C1—C13—C12	85.34 (12)	C15—C14—C19—C20	−41.57 (16)
C2—C1—C13—C12	−40.98 (14)	C13—C14—C19—C20	−168.57 (12)
N1—C1—C13—C14	−37.80 (12)	C20—C19—C24—C23	−0.1 (2)
C2—C1—C13—C14	−164.12 (10)	C14—C19—C24—C23	173.86 (13)
C11—O1—C12—C13	−45.96 (17)	C19—C24—C23—C22	1.2 (2)
C25—C13—C12—O1	−64.37 (14)	C24—C23—C22—C21	−1.3 (2)
C1—C13—C12—O1	58.76 (15)	C23—C22—C21—C20	0.2 (2)
C14—C13—C12—O1	169.77 (11)	C22—C21—C20—C19	0.9 (2)
C2—C1—N1—C18	24.13 (16)	C24—C19—C20—C21	−0.9 (2)
C13—C1—N1—C18	−101.18 (13)	C14—C19—C20—C21	−175.28 (13)

Cg1 and Cg2 are the centroids of the C3–C8 and C19–C24 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···O2	0.93	2.59	3.388 (2)	145
C7—H7···Cg2i	0.93	2.82	3.6435 (17)	148
C17—H17A···Cg2ii	0.97	2.78	3.7065 (17)	159
C21—H21···Cg1iii	0.93	2.49	3.4174 (18)	175
C26—H26B···Cg1iv	0.96	2.58	3.477 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C3–C8 and C19–C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24⋯O2	0.93	2.59	3.388 (2)	145
C7—H7⋯Cg2i	0.93	2.82	3.6435 (17)	148
C17—H17A⋯Cg2ii	0.97	2.78	3.7065 (17)	159
C21—H21⋯Cg1iii	0.93	2.49	3.4174 (18)	175
C26—H26B⋯Cg1iv	0.96	2.58	3.477 (2)	156

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .