(7R,8S,8aS)-8-Hydr-oxy-7-phenyl-perhydro-indolizin-3-one.

In the title compound, C(14)H(17)NO(2), the six-membered ring of the indolizine system adopts a chair conformation. In the crystal, mol-ecules form chains parallel to the b axis via inter-molecular O-H⋯O hydrogen bonds. The absolute mol-ecular configuration was assigned from the synthesis.

Related literature

For industrial uses of indolizines, see: Jaung & Jung (2003 ▶); Rotaru et al. (2005 ▶); Delattre et al. (2005 ▶); Kelin et al. (2001 ▶). For biological uses, see: Nash et al. (1988 ▶); Molyneux & James (1982 ▶); Harrell (1970 ▶); Ruprecht et al. (1989 ▶); Liu et al. (2007 ▶); Smith et al. (2007 ▶); Gupta et al. (2003 ▶); Rosseels et al. (1982 ▶); Oslund et al. (2008 ▶); Ostby et al. (2000 ▶). For synthesis of indolizines, see: Chuprakov & Gevorgyan (2007 ▶); Yan & Liu (2007 ▶). For the synthesis methods used, see: Šafář et al. (2009 ▶). For structures related to the title compound, see: Švorc et al. (2009 ▶). For comparison of mol­ecular parameters, see: Camus et al. (2003 ▶); Lokaj et al. (1999 ▶); Brown & Corbridge (1954 ▶); Pedersen (1967 ▶). For a general analysis of puckering, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C14H17NO2

M = 231.29

Orthorhombic,

a = 11.4164 (3) Å

b = 6.6372 (2) Å

c = 15.5118 (4) Å

V = 1175.38 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.60 × 0.56 × 0.13 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical (Clark & Reid, 1995 ▶) T min = 0.901, T max = 0.989

26298 measured reflections

1632 independent reflections

1128 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.101

S = 1.03

1632 reflections

157 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.12 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2001 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018455/bg2260sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018455/bg2260Isup2.hkl

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

C14H17NO2	F(000) = 496
Mr = 231.29	Dx = 1.307 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 13180 reflections
a = 11.4164 (3) Å	θ = 3.3–29.4°
b = 6.6372 (2) Å	µ = 0.09 mm−1
c = 15.5118 (4) Å	T = 298 K
V = 1175.38 (6) Å3	Block, white
Z = 4	0.60 × 0.56 × 0.13 mm

Oxford Diffraction Gemini R CCD diffractometer	1632 independent reflections
Radiation source: fine-focus sealed tube	1128 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 10.4340 pixels mm-1	θmax = 29.4°, θmin = 3.6°
Rotation method data acquisition using ω and φ scans	h = −15→15
Absorption correction: analytical (Clark & Reid, 1995)	k = −9→9
Tmin = 0.901, Tmax = 0.989	l = −20→21
26298 measured reflections

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0644P)2 + 0.0334P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1632 reflections	Δρmax = 0.17 e Å−3
157 parameters	Δρmin = −0.12 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (4)

Experimental. face-indexed (CrysAlis RED; Oxford Diffraction, 2006)

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	0.2640 (2)	−0.3204 (3)	0.32882 (13)	0.0425 (5)
C3	0.21718 (19)	−0.1773 (3)	0.26133 (17)	0.0490 (5)
H3A	0.1398	−0.1296	0.2773	0.059*
H3B	0.2121	−0.2438	0.2058	0.059*
C4	0.3027 (2)	−0.0043 (4)	0.25750 (16)	0.0590 (6)
H4A	0.2626	0.1227	0.2670	0.071*
H4B	0.3409	0.0003	0.2017	0.071*
C5	0.3932 (2)	−0.0428 (3)	0.32948 (15)	0.0466 (5)
H5	0.4708	−0.0578	0.3033	0.056*
C6	0.40010 (17)	0.1156 (3)	0.40092 (13)	0.0400 (4)
H6	0.4340	0.2393	0.3771	0.048*
C7	0.47970 (18)	0.0382 (3)	0.47386 (13)	0.0421 (5)
H7	0.5558	0.0075	0.4478	0.051*
C8	0.4309 (2)	−0.1608 (3)	0.50890 (16)	0.0514 (6)
H8A	0.4814	−0.2100	0.5545	0.062*
H8B	0.3537	−0.1378	0.5332	0.062*
C9	0.4226 (2)	−0.3184 (3)	0.43821 (15)	0.0557 (6)
H9A	0.5006	−0.3569	0.4197	0.067*
H9B	0.3832	−0.4375	0.4600	0.067*
C10	0.50152 (16)	0.1935 (3)	0.54318 (14)	0.0407 (5)
C11	0.42606 (19)	0.2235 (4)	0.61193 (16)	0.0507 (5)
H11	0.3582	0.1464	0.6159	0.061*
C12	0.4494 (2)	0.3654 (4)	0.67466 (16)	0.0580 (6)
H12	0.3976	0.3833	0.7203	0.070*
C13	0.5498 (2)	0.4808 (4)	0.66972 (17)	0.0599 (7)
H13	0.5662	0.5754	0.7122	0.072*
C14	0.6248 (2)	0.4553 (4)	0.60216 (17)	0.0623 (7)
H14	0.6919	0.5343	0.5982	0.075*
C15	0.60156 (19)	0.3120 (4)	0.53928 (16)	0.0501 (5)
H15	0.6538	0.2951	0.4938	0.060*
N1	0.35736 (17)	−0.2359 (3)	0.36550 (12)	0.0473 (4)
O1	0.22237 (14)	−0.4869 (2)	0.34724 (11)	0.0545 (5)
O2	0.28771 (12)	0.1598 (2)	0.43433 (11)	0.0496 (4)
H2	0.2647	0.2673	0.4146	0.074*

	U11	U22	U33	U12	U13	U23
C2	0.0503 (12)	0.0381 (10)	0.0391 (11)	0.0064 (9)	0.0004 (9)	−0.0066 (9)
C3	0.0507 (13)	0.0483 (11)	0.0480 (12)	0.0040 (9)	−0.0032 (10)	0.0014 (10)
C4	0.0858 (18)	0.0477 (12)	0.0436 (12)	−0.0088 (11)	−0.0148 (13)	0.0042 (10)
C5	0.0585 (13)	0.0404 (10)	0.0408 (10)	−0.0013 (9)	−0.0015 (10)	0.0023 (9)
C6	0.0488 (11)	0.0331 (10)	0.0382 (10)	−0.0015 (8)	0.0012 (9)	0.0038 (8)
C7	0.0395 (10)	0.0449 (12)	0.0419 (11)	0.0035 (8)	−0.0023 (9)	−0.0003 (9)
C8	0.0681 (15)	0.0384 (11)	0.0478 (11)	0.0032 (10)	−0.0163 (11)	0.0054 (9)
C9	0.0736 (15)	0.0366 (11)	0.0570 (14)	0.0078 (9)	−0.0211 (12)	0.0039 (10)
C10	0.0405 (10)	0.0417 (11)	0.0397 (10)	0.0017 (8)	−0.0059 (9)	0.0024 (8)
C11	0.0523 (11)	0.0496 (12)	0.0501 (12)	0.0022 (9)	0.0080 (11)	−0.0004 (10)
C12	0.0783 (16)	0.0509 (12)	0.0447 (12)	0.0132 (12)	0.0045 (12)	−0.0045 (11)
C13	0.0818 (17)	0.0480 (12)	0.0500 (13)	0.0058 (11)	−0.0209 (13)	−0.0055 (11)
C14	0.0621 (14)	0.0556 (14)	0.0693 (16)	−0.0098 (11)	−0.0195 (14)	0.0004 (12)
C15	0.0453 (11)	0.0587 (13)	0.0464 (12)	−0.0024 (10)	−0.0031 (10)	0.0035 (10)
N1	0.0593 (11)	0.0359 (9)	0.0465 (9)	0.0005 (8)	−0.0100 (8)	0.0014 (8)
O1	0.0640 (11)	0.0413 (8)	0.0582 (11)	−0.0047 (6)	−0.0065 (8)	0.0027 (7)
O2	0.0456 (8)	0.0486 (8)	0.0546 (9)	0.0083 (6)	0.0023 (7)	0.0085 (7)

C2—O1	1.237 (2)	C8—C9	1.518 (3)
C2—N1	1.332 (3)	C8—H8A	0.9700
C2—C3	1.511 (3)	C8—H8B	0.9700
C3—C4	1.508 (3)	C9—N1	1.458 (3)
C3—H3A	0.9700	C9—H9A	0.9700
C3—H3B	0.9700	C9—H9B	0.9700
C4—C5	1.542 (3)	C10—C11	1.385 (3)
C4—H4A	0.9700	C10—C15	1.388 (3)
C4—H4B	0.9700	C11—C12	1.380 (3)
C5—N1	1.457 (3)	C11—H11	0.9300
C5—C6	1.530 (3)	C12—C13	1.380 (4)
C5—H5	0.9800	C12—H12	0.9300
C6—O2	1.414 (2)	C13—C14	1.364 (4)
C6—C7	1.540 (3)	C13—H13	0.9300
C6—H6	0.9800	C14—C15	1.388 (3)
C7—C10	1.510 (3)	C14—H14	0.9300
C7—C8	1.533 (3)	C15—H15	0.9300
C7—H7	0.9800	O2—H2	0.8200
O1—C2—N1	125.78 (19)	C9—C8—H8A	109.4
O1—C2—C3	125.9 (2)	C7—C8—H8A	109.4
N1—C2—C3	108.33 (17)	C9—C8—H8B	109.4
C2—C3—C4	106.09 (18)	C7—C8—H8B	109.4
C2—C3—H3A	110.5	H8A—C8—H8B	108.0
C4—C3—H3A	110.5	N1—C9—C8	109.40 (16)
C2—C3—H3B	110.5	N1—C9—H9A	109.8
C4—C3—H3B	110.5	C8—C9—H9A	109.8
H3A—C3—H3B	108.7	N1—C9—H9B	109.8
C3—C4—C5	106.18 (18)	C8—C9—H9B	109.8
C3—C4—H4A	110.5	H9A—C9—H9B	108.2
C5—C4—H4A	110.5	C11—C10—C15	117.7 (2)
C3—C4—H4B	110.5	C11—C10—C7	122.92 (19)
C5—C4—H4B	110.5	C15—C10—C7	119.4 (2)
H4A—C4—H4B	108.7	C10—C11—C12	121.4 (2)
N1—C5—C6	109.98 (17)	C10—C11—H11	119.3
N1—C5—C4	103.63 (18)	C12—C11—H11	119.3
C6—C5—C4	116.45 (19)	C13—C12—C11	120.0 (2)
N1—C5—H5	108.8	C13—C12—H12	120.0
C6—C5—H5	108.8	C11—C12—H12	120.0
C4—C5—H5	108.8	C14—C13—C12	119.7 (2)
O2—C6—C5	111.15 (17)	C14—C13—H13	120.2
O2—C6—C7	109.59 (16)	C12—C13—H13	120.2
C5—C6—C7	109.49 (16)	C13—C14—C15	120.3 (2)
O2—C6—H6	108.9	C13—C14—H14	119.9
C5—C6—H6	108.9	C15—C14—H14	119.9
C7—C6—H6	108.9	C10—C15—C14	121.0 (2)
C10—C7—C6	113.12 (15)	C10—C15—H15	119.5
C10—C7—C8	113.31 (18)	C14—C15—H15	119.5
C6—C7—C8	109.48 (17)	C2—N1—C5	115.52 (17)
C10—C7—H7	106.8	C2—N1—C9	125.54 (18)
C6—C7—H7	106.8	C5—N1—C9	118.92 (18)
C8—C7—H7	106.8	C6—O2—H2	109.5
C9—C8—C7	111.1 (2)
O1—C2—C3—C4	−175.3 (2)	C8—C7—C10—C15	139.5 (2)
N1—C2—C3—C4	5.1 (2)	C15—C10—C11—C12	−0.3 (3)
C2—C3—C4—C5	−4.7 (2)	C7—C10—C11—C12	179.3 (2)
C3—C4—C5—N1	2.8 (2)	C10—C11—C12—C13	−0.1 (4)
C3—C4—C5—C6	−118.0 (2)	C11—C12—C13—C14	0.7 (4)
N1—C5—C6—O2	−67.5 (2)	C12—C13—C14—C15	−1.0 (4)
C4—C5—C6—O2	50.0 (2)	C11—C10—C15—C14	0.0 (3)
N1—C5—C6—C7	53.7 (2)	C7—C10—C15—C14	−179.6 (2)
C4—C5—C6—C7	171.18 (18)	C13—C14—C15—C10	0.6 (3)
O2—C6—C7—C10	−63.7 (2)	O1—C2—N1—C5	176.9 (2)
C5—C6—C7—C10	174.18 (17)	C3—C2—N1—C5	−3.5 (2)
O2—C6—C7—C8	63.7 (2)	O1—C2—N1—C9	−4.6 (3)
C5—C6—C7—C8	−58.4 (2)	C3—C2—N1—C9	175.0 (2)
C10—C7—C8—C9	−174.06 (18)	C6—C5—N1—C2	125.53 (19)
C6—C7—C8—C9	58.6 (2)	C4—C5—N1—C2	0.4 (2)
C7—C8—C9—N1	−52.9 (3)	C6—C5—N1—C9	−53.1 (3)
C6—C7—C10—C11	85.3 (2)	C4—C5—N1—C9	−178.2 (2)
C8—C7—C10—C11	−40.0 (3)	C8—C9—N1—C2	−126.4 (2)
C6—C7—C10—C15	−95.1 (2)	C8—C9—N1—C5	52.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	2.00	2.807 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	2.00	2.807 (2)	170

Symmetry code: (i) .