Methyl 5-phenyl-1,2,3,4,4a,5,5a,13c-octahydro-6H-benzo[f]chromeno[3,4-b]indolizine-5a-carboxyl-ate.

In the title compound, C(27)H(27)NO(3), the pyrrolidine ring exhibits a twist conformation and the piperidine ring exhibits a chair conformation. The pyrrolidine ring makes dihedral angles of 54.47 (5), 51.50 (5) and 73.37 (6)° with the napthalene ring system and the tetra-hydro-pyran and phenyl rings, respectively. The structure is stabilized by intra-molecular C-H⋯O and C-H⋯N inter-actions.

Related literature

For general background to the applications and biological activity of indolizine derivatives, see: Gubin et al. (1992 ▶); Gupta et al. (2003 ▶); Poty et al. (1994 ▶); Hema et al. (2003 ▶); Malonne et al. (1998 ▶); Medda et al. (2003 ▶). For puckering parameters, see: Cremer and Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶).

Experimental

Crystal data

C27H27NO3

M = 413.50

Triclinic,

a = 9.4201 (3) Å

b = 10.6752 (3) Å

c = 11.0761 (3) Å

α = 78.262 (2)°

β = 77.911 (2)°

γ = 87.346 (2)°

V = 1066.34 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.975, T max = 0.988

22685 measured reflections

4641 independent reflections

3461 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.122

S = 1.00

4641 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: APEX2 and 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 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809026774/bt2988sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026774/bt2988Isup2.hkl

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

C27H27NO3	Z = 2
Mr = 413.50	F(000) = 440
Triclinic, P1	Dx = 1.288 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4201 (3) Å	Cell parameters from 22685 reflections
b = 10.6752 (3) Å	θ = 2.0–27.0°
c = 11.0761 (3) Å	µ = 0.08 mm−1
α = 78.262 (2)°	T = 293 K
β = 77.911 (2)°	Needle, colourless
γ = 87.346 (2)°	0.30 × 0.20 × 0.15 mm
V = 1066.34 (5) Å3

Bruker Kappa APEXII diffractometer	4641 independent reflections
Radiation source: fine-focus sealed tube	3461 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω and φ scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
Tmin = 0.975, Tmax = 0.988	k = −13→13
22685 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0534P)2 + 0.3168P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4641 reflections	Δρmax = 0.34 e Å−3
281 parameters	Δρmin = −0.23 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (2)

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
C1	0.54853 (15)	0.76212 (14)	0.13837 (13)	0.0396 (3)
H1A	0.4898	0.7171	0.2165	0.047*
H1B	0.5454	0.8527	0.1403	0.047*
C2	0.70388 (16)	0.71426 (15)	0.12642 (15)	0.0453 (4)
H2A	0.7052	0.6221	0.1343	0.054*
H2B	0.7439	0.7339	0.1943	0.054*
C3	0.79742 (17)	0.77508 (18)	0.00095 (16)	0.0540 (4)
H3A	0.8930	0.7357	−0.0077	0.065*
H3B	0.8089	0.8655	−0.0016	0.065*
C4	0.72958 (17)	0.75893 (18)	−0.10770 (16)	0.0504 (4)
H4A	0.7854	0.8056	−0.1864	0.060*
H4B	0.7295	0.6692	−0.1125	0.060*
C5	0.57534 (15)	0.80960 (13)	−0.08654 (13)	0.0366 (3)
H5	0.5812	0.8987	−0.0780	0.044*
C6	0.47933 (16)	0.80945 (13)	−0.18463 (13)	0.0378 (3)
H6	0.4643	0.8996	−0.2206	0.045*
C7	0.32917 (15)	0.76056 (13)	−0.10062 (13)	0.0365 (3)
C8	0.33931 (14)	0.78431 (12)	0.02922 (13)	0.0340 (3)
H8	0.3313	0.8762	0.0288	0.041*
C9	0.22386 (15)	0.71384 (13)	0.13304 (13)	0.0376 (3)
C10	0.17673 (15)	0.75355 (14)	0.25133 (14)	0.0412 (3)
C11	0.23444 (18)	0.86035 (16)	0.28129 (15)	0.0476 (4)
H11	0.3068	0.9082	0.2220	0.057*
C12	0.1870 (2)	0.8954 (2)	0.39497 (17)	0.0612 (5)
H12	0.2275	0.9661	0.4118	0.073*
C13	0.0784 (2)	0.8262 (2)	0.48593 (17)	0.0714 (6)
H13	0.0478	0.8495	0.5638	0.086*
C14	0.0178 (2)	0.7247 (2)	0.46007 (17)	0.0658 (5)
H14	−0.0558	0.6797	0.5205	0.079*
C15	0.06357 (17)	0.68546 (16)	0.34362 (15)	0.0501 (4)
C16	−0.00152 (18)	0.58123 (17)	0.31539 (17)	0.0572 (5)
H16	−0.0748	0.5357	0.3758	0.069*
C17	0.04018 (17)	0.54627 (16)	0.20290 (18)	0.0540 (4)
H17	−0.0050	0.4782	0.1857	0.065*
C18	0.15284 (16)	0.61359 (14)	0.11133 (15)	0.0431 (4)
C19	0.30894 (17)	0.61779 (14)	−0.08800 (15)	0.0441 (4)
H19A	0.3044	0.6000	−0.1696	0.053*
H19B	0.3921	0.5724	−0.0612	0.053*
C20	0.53277 (16)	0.74536 (14)	−0.29578 (14)	0.0413 (3)
C21	0.59051 (17)	0.62247 (15)	−0.28796 (15)	0.0478 (4)
H21	0.6021	0.5754	−0.2102	0.057*
C22	0.63086 (19)	0.56903 (18)	−0.39354 (18)	0.0571 (4)
H22	0.6691	0.4866	−0.3863	0.069*
C23	0.6149 (2)	0.6367 (2)	−0.50911 (18)	0.0688 (5)
H23	0.6415	0.6004	−0.5801	0.083*
C24	0.5594 (2)	0.7582 (2)	−0.51919 (17)	0.0750 (6)
H24	0.5486	0.8048	−0.5974	0.090*
C25	0.5192 (2)	0.81199 (18)	−0.41372 (15)	0.0589 (5)
H25	0.4823	0.8949	−0.4222	0.071*
C26	0.20768 (16)	0.83093 (14)	−0.15768 (14)	0.0420 (4)
C27	0.0803 (2)	1.02515 (18)	−0.1933 (2)	0.0728 (6)
H27A	0.0737	1.1075	−0.1703	0.109*
H27B	−0.0126	0.9839	−0.1656	0.109*
H27C	0.1093	1.0355	−0.2832	0.109*
N1	0.49017 (12)	0.74134 (10)	0.03267 (10)	0.0349 (3)
O1	0.17989 (12)	0.57199 (10)	0.00045 (11)	0.0524 (3)
O2	0.13962 (15)	0.78741 (13)	−0.21840 (14)	0.0738 (4)
O3	0.18643 (13)	0.94760 (11)	−0.13447 (13)	0.0610 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0406 (8)	0.0426 (8)	0.0360 (8)	0.0003 (6)	−0.0123 (6)	−0.0045 (6)
C2	0.0417 (8)	0.0485 (8)	0.0495 (9)	0.0022 (7)	−0.0186 (7)	−0.0092 (7)
C3	0.0359 (8)	0.0718 (11)	0.0571 (11)	−0.0019 (8)	−0.0116 (7)	−0.0172 (9)
C4	0.0384 (8)	0.0672 (10)	0.0466 (9)	−0.0003 (7)	−0.0068 (7)	−0.0153 (8)
C5	0.0401 (8)	0.0355 (7)	0.0331 (7)	−0.0035 (6)	−0.0068 (6)	−0.0042 (6)
C6	0.0427 (8)	0.0346 (7)	0.0344 (8)	0.0016 (6)	−0.0092 (6)	−0.0020 (6)
C7	0.0380 (7)	0.0355 (7)	0.0368 (8)	0.0032 (6)	−0.0112 (6)	−0.0062 (6)
C8	0.0354 (7)	0.0320 (6)	0.0348 (7)	0.0028 (5)	−0.0116 (6)	−0.0035 (5)
C9	0.0332 (7)	0.0377 (7)	0.0384 (8)	0.0052 (6)	−0.0093 (6)	0.0010 (6)
C10	0.0353 (7)	0.0467 (8)	0.0377 (8)	0.0105 (6)	−0.0105 (6)	0.0016 (6)
C11	0.0452 (9)	0.0583 (9)	0.0393 (8)	0.0089 (7)	−0.0116 (7)	−0.0083 (7)
C12	0.0594 (11)	0.0808 (13)	0.0485 (10)	0.0128 (9)	−0.0170 (9)	−0.0209 (9)
C13	0.0698 (13)	0.1044 (17)	0.0372 (10)	0.0179 (12)	−0.0085 (9)	−0.0145 (10)
C14	0.0548 (11)	0.0877 (14)	0.0406 (10)	0.0156 (10)	0.0001 (8)	0.0062 (9)
C15	0.0393 (8)	0.0583 (10)	0.0431 (9)	0.0113 (7)	−0.0065 (7)	0.0075 (7)
C16	0.0392 (9)	0.0582 (10)	0.0591 (11)	0.0025 (8)	0.0005 (8)	0.0119 (8)
C17	0.0380 (8)	0.0464 (9)	0.0707 (12)	−0.0031 (7)	−0.0078 (8)	0.0018 (8)
C18	0.0356 (7)	0.0408 (8)	0.0492 (9)	0.0031 (6)	−0.0088 (7)	−0.0013 (7)
C19	0.0437 (8)	0.0409 (8)	0.0480 (9)	−0.0014 (6)	−0.0076 (7)	−0.0113 (7)
C20	0.0406 (8)	0.0486 (8)	0.0342 (8)	−0.0004 (6)	−0.0088 (6)	−0.0058 (6)
C21	0.0476 (9)	0.0520 (9)	0.0443 (9)	0.0055 (7)	−0.0102 (7)	−0.0111 (7)
C22	0.0482 (9)	0.0654 (11)	0.0605 (11)	0.0050 (8)	−0.0059 (8)	−0.0255 (9)
C23	0.0632 (12)	0.0998 (16)	0.0486 (11)	0.0020 (11)	−0.0046 (9)	−0.0338 (11)
C24	0.0890 (15)	0.1004 (16)	0.0344 (10)	0.0088 (13)	−0.0153 (10)	−0.0098 (10)
C25	0.0689 (12)	0.0660 (11)	0.0385 (9)	0.0091 (9)	−0.0128 (8)	−0.0031 (8)
C26	0.0432 (8)	0.0482 (8)	0.0380 (8)	0.0029 (7)	−0.0154 (7)	−0.0098 (6)
C27	0.0742 (13)	0.0566 (11)	0.0990 (16)	0.0198 (9)	−0.0548 (12)	−0.0080 (10)
N1	0.0328 (6)	0.0373 (6)	0.0334 (6)	0.0007 (5)	−0.0090 (5)	−0.0022 (5)
O1	0.0482 (6)	0.0477 (6)	0.0609 (7)	−0.0112 (5)	−0.0050 (5)	−0.0140 (5)
O2	0.0823 (10)	0.0762 (9)	0.0850 (10)	0.0176 (7)	−0.0542 (8)	−0.0328 (8)
O3	0.0680 (8)	0.0456 (6)	0.0851 (9)	0.0183 (5)	−0.0509 (7)	−0.0167 (6)

C1—N1	1.4521 (18)	C12—H12	0.9300
C1—C2	1.5157 (19)	C13—C14	1.355 (3)
C1—H1A	0.9700	C13—H13	0.9300
C1—H1B	0.9700	C14—C15	1.412 (3)
C2—C3	1.517 (2)	C14—H14	0.9300
C2—H2A	0.9700	C15—C16	1.413 (3)
C2—H2B	0.9700	C16—C17	1.348 (3)
C3—C4	1.518 (2)	C16—H16	0.9300
C3—H3A	0.9700	C17—C18	1.412 (2)
C3—H3B	0.9700	C17—H17	0.9300
C4—C5	1.515 (2)	C18—O1	1.3604 (19)
C4—H4A	0.9700	C19—O1	1.4276 (18)
C4—H4B	0.9700	C19—H19A	0.9700
C5—N1	1.4618 (17)	C19—H19B	0.9700
C5—C6	1.553 (2)	C20—C25	1.383 (2)
C5—H5	0.9800	C20—C21	1.390 (2)
C6—C20	1.5128 (19)	C21—C22	1.379 (2)
C6—C7	1.568 (2)	C21—H21	0.9300
C6—H6	0.9800	C22—C23	1.370 (3)
C7—C26	1.5178 (19)	C22—H22	0.9300
C7—C19	1.5191 (19)	C23—C24	1.368 (3)
C7—C8	1.5328 (19)	C23—H23	0.9300
C8—N1	1.4788 (16)	C24—C25	1.380 (3)
C8—C9	1.5070 (19)	C24—H24	0.9300
C8—H8	0.9800	C25—H25	0.9300
C9—C18	1.375 (2)	C26—O2	1.1892 (18)
C9—C10	1.435 (2)	C26—O3	1.3203 (18)
C10—C11	1.412 (2)	C27—O3	1.4445 (18)
C10—C15	1.422 (2)	C27—H27A	0.9600
C11—C12	1.366 (2)	C27—H27B	0.9600
C11—H11	0.9300	C27—H27C	0.9600
C12—C13	1.393 (3)
N1—C1—C2	110.04 (12)	C11—C12—H12	119.7
N1—C1—H1A	109.7	C13—C12—H12	119.7
C2—C1—H1A	109.7	C14—C13—C12	119.46 (18)
N1—C1—H1B	109.7	C14—C13—H13	120.3
C2—C1—H1B	109.7	C12—C13—H13	120.3
H1A—C1—H1B	108.2	C13—C14—C15	121.63 (18)
C1—C2—C3	111.46 (13)	C13—C14—H14	119.2
C1—C2—H2A	109.3	C15—C14—H14	119.2
C3—C2—H2A	109.3	C14—C15—C16	121.75 (17)
C1—C2—H2B	109.3	C14—C15—C10	119.33 (18)
C3—C2—H2B	109.3	C16—C15—C10	118.91 (15)
H2A—C2—H2B	108.0	C17—C16—C15	121.48 (16)
C2—C3—C4	110.99 (14)	C17—C16—H16	119.3
C2—C3—H3A	109.4	C15—C16—H16	119.3
C4—C3—H3A	109.4	C16—C17—C18	119.65 (17)
C2—C3—H3B	109.4	C16—C17—H17	120.2
C4—C3—H3B	109.4	C18—C17—H17	120.2
H3A—C3—H3B	108.0	O1—C18—C9	124.15 (14)
C5—C4—C3	108.85 (13)	O1—C18—C17	113.58 (14)
C5—C4—H4A	109.9	C9—C18—C17	122.24 (15)
C3—C4—H4A	109.9	O1—C19—C7	111.98 (12)
C5—C4—H4B	109.9	O1—C19—H19A	109.2
C3—C4—H4B	109.9	C7—C19—H19A	109.2
H4A—C4—H4B	108.3	O1—C19—H19B	109.2
N1—C5—C4	110.61 (12)	C7—C19—H19B	109.2
N1—C5—C6	104.91 (11)	H19A—C19—H19B	107.9
C4—C5—C6	120.75 (12)	C25—C20—C21	117.25 (15)
N1—C5—H5	106.6	C25—C20—C6	117.84 (14)
C4—C5—H5	106.6	C21—C20—C6	124.88 (13)
C6—C5—H5	106.6	C22—C21—C20	121.16 (16)
C20—C6—C5	120.22 (12)	C22—C21—H21	119.4
C20—C6—C7	115.04 (12)	C20—C21—H21	119.4
C5—C6—C7	103.10 (11)	C23—C22—C21	120.37 (17)
C20—C6—H6	105.8	C23—C22—H22	119.8
C5—C6—H6	105.8	C21—C22—H22	119.8
C7—C6—H6	105.8	C24—C23—C22	119.46 (17)
C26—C7—C19	108.51 (12)	C24—C23—H23	120.3
C26—C7—C8	115.68 (11)	C22—C23—H23	120.3
C19—C7—C8	107.65 (11)	C23—C24—C25	120.25 (18)
C26—C7—C6	109.40 (11)	C23—C24—H24	119.9
C19—C7—C6	112.66 (11)	C25—C24—H24	119.9
C8—C7—C6	102.97 (11)	C24—C25—C20	121.49 (18)
N1—C8—C9	115.59 (10)	C24—C25—H25	119.3
N1—C8—C7	99.80 (10)	C20—C25—H25	119.3
C9—C8—C7	112.33 (12)	O2—C26—O3	123.07 (14)
N1—C8—H8	109.6	O2—C26—C7	124.22 (14)
C9—C8—H8	109.6	O3—C26—C7	112.70 (12)
C7—C8—H8	109.6	O3—C27—H27A	109.5
C18—C9—C10	118.14 (13)	O3—C27—H27B	109.5
C18—C9—C8	119.29 (13)	H27A—C27—H27B	109.5
C10—C9—C8	122.39 (13)	O3—C27—H27C	109.5
C11—C10—C15	117.06 (15)	H27A—C27—H27C	109.5
C11—C10—C9	123.40 (14)	H27B—C27—H27C	109.5
C15—C10—C9	119.52 (15)	C1—N1—C5	110.91 (11)
C12—C11—C10	121.81 (17)	C1—N1—C8	116.93 (11)
C12—C11—H11	119.1	C5—N1—C8	104.15 (10)
C10—C11—H11	119.1	C18—O1—C19	116.88 (12)
C11—C12—C13	120.7 (2)	C26—O3—C27	116.46 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3	0.98	2.47	2.8240 (19)	101
C19—H19B···N1	0.97	2.55	2.885 (2)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O3	0.98	2.47	2.8240 (19)	101
C19—H19B⋯N1	0.97	2.55	2.885 (2)	100