(3aS,9bR)-Methyl 1-methyl-3-phenyl-1,2,3,3a,4,9b-hexa-hydro-chromeno[4,3-b]pyrrole-3a-carboxyl-ate.

In the title compound, C(20)H(21)NO(3), the heterocyclic six-membered ring adopts a half-chair conformation and the pyrrolidine ring adopts an envelope conformation. The mol-ecular conformation is stabilized by C-H⋯O and C-H⋯N inter-actions.

Related literature

For related literature, see: Brockmann & Tour (1995 ▶); Caine (1993 ▶); Carlson (1993 ▶); Cremer & Pople (1975 ▶); Di Natale et al. (1998 ▶); Nirmala et al. (2008 ▶); Sobral & Rocha Gonsalves (2001a ▶,b ▶); Sokoloff et al. (1990 ▶); Suslick et al. (1992 ▶); Tidey (1992 ▶); Wilner (1985 ▶).

Experimental

Crystal data

C20H21NO3

M = 323.38

Triclinic,

a = 7.9557 (4) Å

b = 10.2575 (7) Å

c = 10.2993 (8) Å

α = 79.626 (5)°

β = 87.361 (5)°

γ = 88.744 (4)°

V = 825.79 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.20 × 0.20 × 0.12 mm

Data collection

Bruker Kappa APEX2 diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.983, T max = 0.990

18704 measured reflections

4126 independent reflections

3051 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.143

S = 1.03

4126 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2/SAINT (Bruker, 2004 ▶); data reduction: SAINT/XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808005199/bt2680sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005199/bt2680Isup2.hkl

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

C20H21NO3	Z = 2
Mr = 323.38	F000 = 344
Triclinic, P1	Dx = 1.301 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.9557 (4) Å	Cell parameters from 5117 reflections
b = 10.2575 (7) Å	θ = 2.6–28.1º
c = 10.2993 (8) Å	µ = 0.09 mm−1
α = 79.626 (5)º	T = 293 (2) K
β = 87.361 (5)º	Prism, colourless
γ = 88.744 (4)º	0.20 × 0.20 × 0.12 mm
V = 825.79 (9) Å3

Bruker KappaAPEX2 diffractometer	4126 independent reflections
Radiation source: fine-focus sealed tube	3051 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 293(2) K	θmax = 28.4º
ω and φ scans	θmin = 2.6º
Absorption correction: multi-scan(Blessing, 1995)	h = −10→10
Tmin = 0.983, Tmax = 0.990	k = −13→13
18704 measured reflections	l = −13→13

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.046	w = 1/[σ2(Fo2) + (0.0739P)2 + 0.1492P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.143	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.23 e Å−3
4126 reflections	Δρmin = −0.21 e Å−3
218 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (5)
Secondary atom site location: difference Fourier map

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
C2	0.58609 (18)	0.33276 (15)	0.84198 (19)	0.0553 (4)
H2A	0.6321	0.3161	0.9291	0.066*
H2B	0.6651	0.2989	0.7811	0.066*
C3	0.41543 (16)	0.26557 (14)	0.84521 (15)	0.0396 (3)
H3	0.4205	0.2149	0.7730	0.047*
C4	0.29028 (15)	0.38426 (13)	0.80439 (13)	0.0347 (3)
C5	0.22346 (17)	0.44251 (15)	0.92274 (14)	0.0416 (3)
H5A	0.1512	0.3786	0.9785	0.050*
H5B	0.3170	0.4595	0.9742	0.050*
C6	0.19789 (18)	0.65300 (15)	0.78280 (15)	0.0437 (3)
C7	0.1233 (2)	0.77835 (17)	0.7635 (2)	0.0589 (5)
H7	0.0357	0.7975	0.8203	0.071*
C8	0.1789 (3)	0.87321 (18)	0.6611 (2)	0.0681 (5)
H8	0.1299	0.9574	0.6494	0.082*
C9	0.3069 (3)	0.84568 (17)	0.5748 (2)	0.0649 (5)
H9	0.3438	0.9106	0.5049	0.078*
C10	0.3803 (2)	0.72004 (15)	0.59337 (16)	0.0496 (4)
H10	0.4655	0.7010	0.5345	0.060*
C11	0.32870 (17)	0.62246 (13)	0.69811 (14)	0.0378 (3)
C12	0.40618 (15)	0.48584 (13)	0.71947 (13)	0.0342 (3)
H12	0.4335	0.4590	0.6342	0.041*
C13	0.36182 (15)	0.17036 (13)	0.96874 (14)	0.0366 (3)
C14	0.4024 (2)	0.18592 (16)	1.09382 (16)	0.0493 (4)
H14	0.4679	0.2571	1.1041	0.059*
C15	0.3472 (2)	0.09747 (18)	1.20362 (17)	0.0581 (4)
H15	0.3762	0.1092	1.2872	0.070*
C16	0.2497 (2)	−0.00770 (16)	1.19071 (18)	0.0549 (4)
H16	0.2121	−0.0669	1.2652	0.066*
C17	0.2083 (2)	−0.02486 (16)	1.06844 (19)	0.0545 (4)
H17	0.1417	−0.0957	1.0590	0.065*
C18	0.26509 (19)	0.06275 (14)	0.95821 (16)	0.0457 (4)
H18	0.2376	0.0491	0.8749	0.055*
C19	0.70301 (18)	0.53858 (16)	0.72905 (17)	0.0475 (4)
H19A	0.6792	0.6314	0.7017	0.071*
H19B	0.7314	0.4995	0.6528	0.071*
H19C	0.7958	0.5274	0.7866	0.071*
C20	0.14592 (16)	0.33900 (14)	0.73480 (15)	0.0402 (3)
C21	0.0540 (3)	0.2860 (3)	0.5379 (2)	0.0892 (8)
H21A	0.0932	0.2878	0.4480	0.134*
H21B	−0.0460	0.3399	0.5394	0.134*
H21C	0.0293	0.1965	0.5790	0.134*
N1	0.55638 (13)	0.47446 (11)	0.79846 (12)	0.0380 (3)
O1	0.13061 (13)	0.56333 (11)	0.88343 (11)	0.0525 (3)
O2	0.18247 (17)	0.33696 (15)	0.60870 (12)	0.0735 (4)
O3	0.01458 (14)	0.30253 (14)	0.78731 (13)	0.0663 (4)

	U11	U22	U33	U12	U13	U23
C2	0.0314 (7)	0.0475 (9)	0.0774 (12)	0.0001 (6)	0.0029 (7)	0.0128 (8)
C3	0.0345 (6)	0.0368 (7)	0.0449 (8)	0.0008 (5)	0.0034 (5)	−0.0021 (6)
C4	0.0303 (6)	0.0362 (7)	0.0352 (7)	−0.0009 (5)	0.0013 (5)	−0.0008 (5)
C5	0.0375 (7)	0.0475 (8)	0.0367 (7)	0.0044 (6)	0.0044 (5)	−0.0014 (6)
C6	0.0445 (7)	0.0421 (8)	0.0459 (8)	0.0049 (6)	−0.0105 (6)	−0.0102 (6)
C7	0.0607 (10)	0.0490 (9)	0.0705 (12)	0.0145 (8)	−0.0175 (8)	−0.0182 (8)
C8	0.0816 (13)	0.0407 (9)	0.0842 (14)	0.0108 (8)	−0.0357 (11)	−0.0102 (9)
C9	0.0842 (13)	0.0419 (9)	0.0646 (11)	−0.0123 (8)	−0.0285 (10)	0.0087 (8)
C10	0.0588 (9)	0.0441 (8)	0.0440 (8)	−0.0119 (7)	−0.0114 (7)	0.0008 (6)
C11	0.0410 (7)	0.0357 (7)	0.0369 (7)	−0.0036 (5)	−0.0096 (5)	−0.0045 (5)
C12	0.0335 (6)	0.0364 (7)	0.0319 (7)	−0.0044 (5)	0.0026 (5)	−0.0044 (5)
C13	0.0317 (6)	0.0327 (6)	0.0436 (8)	0.0012 (5)	−0.0033 (5)	−0.0023 (5)
C14	0.0550 (9)	0.0426 (8)	0.0505 (9)	−0.0078 (6)	−0.0114 (7)	−0.0055 (7)
C15	0.0734 (11)	0.0560 (10)	0.0427 (9)	0.0043 (8)	−0.0094 (8)	−0.0016 (7)
C16	0.0571 (9)	0.0445 (9)	0.0544 (10)	0.0041 (7)	0.0048 (7)	0.0118 (7)
C17	0.0491 (8)	0.0374 (8)	0.0730 (12)	−0.0097 (6)	−0.0068 (8)	0.0034 (7)
C18	0.0488 (8)	0.0376 (7)	0.0502 (9)	−0.0050 (6)	−0.0110 (6)	−0.0039 (6)
C19	0.0357 (7)	0.0492 (8)	0.0560 (9)	−0.0088 (6)	0.0068 (6)	−0.0059 (7)
C20	0.0356 (6)	0.0371 (7)	0.0452 (8)	−0.0037 (5)	−0.0020 (6)	0.0007 (6)
C21	0.0921 (15)	0.122 (2)	0.0567 (12)	−0.0647 (15)	−0.0106 (11)	−0.0160 (12)
N1	0.0288 (5)	0.0415 (6)	0.0416 (6)	−0.0025 (4)	0.0015 (4)	−0.0022 (5)
O1	0.0496 (6)	0.0525 (6)	0.0521 (7)	0.0144 (5)	0.0101 (5)	−0.0058 (5)
O2	0.0680 (8)	0.1103 (11)	0.0448 (7)	−0.0518 (8)	0.0016 (6)	−0.0162 (7)
O3	0.0368 (6)	0.0932 (10)	0.0680 (8)	−0.0181 (6)	0.0043 (5)	−0.0116 (7)

C2—N1	1.4593 (19)	C11—C12	1.5020 (18)
C2—C3	1.532 (2)	C12—N1	1.4672 (17)
C2—H2A	0.9700	C12—H12	0.9800
C2—H2B	0.9700	C13—C14	1.380 (2)
C3—C13	1.5083 (19)	C13—C18	1.382 (2)
C3—C4	1.5657 (17)	C14—C15	1.377 (2)
C3—H3	0.9800	C14—H14	0.9300
C4—C20	1.5058 (19)	C15—C16	1.371 (3)
C4—C5	1.5211 (19)	C15—H15	0.9300
C4—C12	1.5298 (17)	C16—C17	1.358 (3)
C5—O1	1.4326 (16)	C16—H16	0.9300
C5—H5A	0.9700	C17—C18	1.380 (2)
C5—H5B	0.9700	C17—H17	0.9300
C6—O1	1.3542 (19)	C18—H18	0.9300
C6—C7	1.389 (2)	C19—N1	1.4464 (17)
C6—C11	1.394 (2)	C19—H19A	0.9600
C7—C8	1.364 (3)	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600
C8—C9	1.379 (3)	C20—O3	1.1901 (17)
C8—H8	0.9300	C20—O2	1.3215 (19)
C9—C10	1.388 (2)	C21—O2	1.442 (2)
C9—H9	0.9300	C21—H21A	0.9600
C10—C11	1.386 (2)	C21—H21B	0.9600
C10—H10	0.9300	C21—H21C	0.9600
N1—C2—C3	106.72 (11)	N1—C12—C4	101.59 (10)
N1—C2—H2A	110.4	C11—C12—C4	111.76 (10)
C3—C2—H2A	110.4	N1—C12—H12	110.0
N1—C2—H2B	110.4	C11—C12—H12	110.0
C3—C2—H2B	110.4	C4—C12—H12	110.0
H2A—C2—H2B	108.6	C14—C13—C18	117.52 (13)
C13—C3—C2	118.02 (13)	C14—C13—C3	123.24 (13)
C13—C3—C4	114.69 (10)	C18—C13—C3	119.23 (13)
C2—C3—C4	103.54 (11)	C15—C14—C13	120.87 (15)
C13—C3—H3	106.6	C15—C14—H14	119.6
C2—C3—H3	106.6	C13—C14—H14	119.6
C4—C3—H3	106.6	C16—C15—C14	120.52 (16)
C20—C4—C5	109.80 (11)	C16—C15—H15	119.7
C20—C4—C12	115.64 (11)	C14—C15—H15	119.7
C5—C4—C12	108.18 (11)	C17—C16—C15	119.55 (15)
C20—C4—C3	109.63 (11)	C17—C16—H16	120.2
C5—C4—C3	112.03 (11)	C15—C16—H16	120.2
C12—C4—C3	101.36 (10)	C16—C17—C18	120.03 (15)
O1—C5—C4	111.89 (11)	C16—C17—H17	120.0
O1—C5—H5A	109.2	C18—C17—H17	120.0
C4—C5—H5A	109.2	C17—C18—C13	121.50 (15)
O1—C5—H5B	109.2	C17—C18—H18	119.3
C4—C5—H5B	109.2	C13—C18—H18	119.3
H5A—C5—H5B	107.9	N1—C19—H19A	109.5
O1—C6—C7	115.99 (14)	N1—C19—H19B	109.5
O1—C6—C11	123.19 (12)	H19A—C19—H19B	109.5
C7—C6—C11	120.76 (15)	N1—C19—H19C	109.5
C8—C7—C6	119.85 (17)	H19A—C19—H19C	109.5
C8—C7—H7	120.1	H19B—C19—H19C	109.5
C6—C7—H7	120.1	O3—C20—O2	122.50 (14)
C7—C8—C9	120.78 (16)	O3—C20—C4	124.50 (14)
C7—C8—H8	119.6	O2—C20—C4	112.91 (11)
C9—C8—H8	119.6	O2—C21—H21A	109.5
C8—C9—C10	119.33 (17)	O2—C21—H21B	109.5
C8—C9—H9	120.3	H21A—C21—H21B	109.5
C10—C9—H9	120.3	O2—C21—H21C	109.5
C11—C10—C9	121.17 (17)	H21A—C21—H21C	109.5
C11—C10—H10	119.4	H21B—C21—H21C	109.5
C9—C10—H10	119.4	C19—N1—C2	111.63 (11)
C10—C11—C6	118.09 (14)	C19—N1—C12	114.08 (11)
C10—C11—C12	121.91 (13)	C2—N1—C12	105.98 (11)
C6—C11—C12	119.97 (12)	C6—O1—C5	117.33 (11)
N1—C12—C11	113.14 (11)	C20—O2—C21	115.98 (14)
N1—C2—C3—C13	−129.88 (13)	C3—C4—C12—C11	−164.30 (11)
N1—C2—C3—C4	−1.93 (17)	C2—C3—C13—C14	33.72 (19)
C13—C3—C4—C20	−79.76 (15)	C4—C3—C13—C14	−88.74 (16)
C2—C3—C4—C20	150.25 (13)	C2—C3—C13—C18	−147.30 (14)
C13—C3—C4—C5	42.41 (16)	C4—C3—C13—C18	90.25 (16)
C2—C3—C4—C5	−87.58 (14)	C18—C13—C14—C15	−0.4 (2)
C13—C3—C4—C12	157.53 (12)	C3—C13—C14—C15	178.62 (14)
C2—C3—C4—C12	27.54 (14)	C13—C14—C15—C16	−0.4 (3)
C20—C4—C5—O1	−67.14 (15)	C14—C15—C16—C17	0.4 (3)
C12—C4—C5—O1	59.90 (14)	C15—C16—C17—C18	0.4 (3)
C3—C4—C5—O1	170.79 (11)	C16—C17—C18—C13	−1.1 (2)
O1—C6—C7—C8	−177.44 (15)	C14—C13—C18—C17	1.1 (2)
C11—C6—C7—C8	−0.4 (2)	C3—C13—C18—C17	−177.91 (13)
C6—C7—C8—C9	1.0 (3)	C5—C4—C20—O3	−28.52 (19)
C7—C8—C9—C10	−0.4 (3)	C12—C4—C20—O3	−151.25 (15)
C8—C9—C10—C11	−0.9 (3)	C3—C4—C20—O3	94.97 (17)
C9—C10—C11—C6	1.6 (2)	C5—C4—C20—O2	154.86 (13)
C9—C10—C11—C12	179.79 (14)	C12—C4—C20—O2	32.13 (17)
O1—C6—C11—C10	175.95 (13)	C3—C4—C20—O2	−81.65 (15)
C7—C6—C11—C10	−0.9 (2)	C3—C2—N1—C19	−150.89 (14)
O1—C6—C11—C12	−2.3 (2)	C3—C2—N1—C12	−26.14 (16)
C7—C6—C11—C12	−179.18 (13)	C11—C12—N1—C19	−72.87 (15)
C10—C11—C12—N1	87.51 (16)	C4—C12—N1—C19	167.17 (11)
C6—C11—C12—N1	−94.28 (15)	C11—C12—N1—C2	163.91 (12)
C10—C11—C12—C4	−158.54 (13)	C4—C12—N1—C2	43.96 (13)
C6—C11—C12—C4	19.67 (18)	C7—C6—O1—C5	−168.00 (14)
C20—C4—C12—N1	−161.84 (11)	C11—C6—O1—C5	15.0 (2)
C5—C4—C12—N1	74.57 (12)	C4—C5—O1—C6	−44.61 (17)
C3—C4—C12—N1	−43.38 (12)	O3—C20—O2—C21	−0.8 (3)
C20—C4—C12—C11	77.23 (14)	C4—C20—O2—C21	175.94 (17)
C5—C4—C12—C11	−46.35 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···N1	0.97	2.55	2.887 (2)	100
C12—H12···O2	0.98	2.43	2.781 (2)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯N1	0.97	2.55	2.887 (2)	100
C12—H12⋯O2	0.98	2.43	2.781 (2)	101