(3aR,8aS,9S,9aR)-9-Hydroxy-perhydro-furo[3,2-f]indolizin-6-one.

In the title compound, C(10)H(15)NO(3), the central six-membered ring of the indolizine system adopts a chair conformation, while the oxopyrrolidine and hydro-furan rings attached to the indolizine ring system have envelope conformations. In the crystal, the mol-ecules form chains parallel to the b axis via inter-molecular O-H⋯O hydrogen bonds. The absolute configuration was assigned from the synthesis.

Related literature

For general properties of indolizines see: Gundersen et al. (2007 ▶); Sundaram et al. (2007 ▶); Mikael (1999 ▶); Pyne (2005 ▶); Karanjule et al. (2006 ▶); Chaudhari et al. (2006 ▶); Martin et al. (2005 ▶). For the synthesis of the title compound see: Šafář et al. (2008 ▶). For related structures, see: Vrábel et al. (2004 ▶); Švorc et al. (2009 ▶). Camus et al. (2003 ▶) For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C10H15NO3

M = 197.23

Monoclinic,

a = 6.2856 (1) Å

b = 6.4521 (1) Å

c = 11.7698 (2) Å

β = 98.631 (2)°

V = 471.92 (1) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.45 × 0.29 × 0.04 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical (Clark & Reid, 1995 ▶) T min = 0.962, T max = 0.996

12197 measured reflections

1359 independent reflections

1151 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.088

S = 1.09

1359 reflections

131 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 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/S1600536809024283/bg2263sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024283/bg2263Isup2.hkl

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

C10H15NO3	F(000) = 212
Mr = 197.23	Dx = 1.388 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7268 reflections
a = 6.2856 (1) Å	θ = 3.2–29.4°
b = 6.4521 (1) Å	µ = 0.10 mm−1
c = 11.7698 (2) Å	T = 298 K
β = 98.631 (2)°	Block, white
V = 471.92 (1) Å3	0.45 × 0.29 × 0.04 mm
Z = 2

Oxford Diffraction Gemini R CCD diffractometer	1359 independent reflections
Radiation source: fine-focus sealed tube	1151 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 10.4340 pixels mm-1	θmax = 29.5°, θmin = 3.5°
Rotation method data acquisition using ω and φ scans	h = −8→8
Absorption correction: analytical (Clark & Reid, 1995)	k = −8→8
Tmin = 0.962, Tmax = 0.996	l = −16→16
12197 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0589P)2 + 0.002P] where P = (Fo2 + 2Fc2)/3
1359 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.12 e Å−3

Experimental. (face-indexed; 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	0.4873 (3)	0.2817 (3)	0.72325 (14)	0.0411 (4)
C3	0.4877 (3)	0.1873 (3)	0.84157 (15)	0.0459 (4)
H3B	0.3467	0.1332	0.8494	0.055*
H3A	0.5921	0.0759	0.8550	0.055*
C4	0.5484 (3)	0.3645 (3)	0.92481 (13)	0.0387 (4)
H4B	0.6470	0.3177	0.9912	0.046*
H4A	0.4216	0.4225	0.9506	0.046*
C5	0.6564 (2)	0.5248 (3)	0.85636 (11)	0.0332 (3)
H5A	0.6105	0.6647	0.8742	0.040*
C6	0.9007 (2)	0.5135 (3)	0.87248 (12)	0.0344 (3)
H6A	0.9426	0.3684	0.8650	0.041*
C7	0.9925 (2)	0.6393 (3)	0.78316 (14)	0.0380 (4)
H7A	1.1473	0.6117	0.7900	0.046*
C8	0.9599 (3)	0.9602 (3)	0.69052 (17)	0.0550 (5)
H8B	1.0849	1.0494	0.6934	0.066*
H8A	0.8315	1.0444	0.6723	0.066*
C9	0.9646 (3)	0.7923 (4)	0.60051 (16)	0.0532 (5)
H9B	1.1088	0.7732	0.5823	0.064*
H9A	0.8680	0.8251	0.5306	0.064*
C10	0.8887 (3)	0.5997 (3)	0.65890 (13)	0.0431 (4)
H10A	0.9444	0.4726	0.6286	0.052*
C11	0.6434 (3)	0.5962 (3)	0.64646 (13)	0.0468 (4)
H11B	0.5898	0.7367	0.6500	0.056*
H11A	0.5847	0.5383	0.5723	0.056*
N1	0.5732 (2)	0.4730 (2)	0.73730 (11)	0.0396 (3)
O1	0.4241 (2)	0.1993 (3)	0.63124 (11)	0.0624 (4)
O2	0.9924 (2)	0.5850 (2)	0.98351 (11)	0.0487 (3)
H2A	0.993 (4)	0.493 (5)	1.031 (2)	0.060 (7)*
O3	0.9608 (2)	0.85665 (19)	0.79966 (10)	0.0471 (3)

	U11	U22	U33	U12	U13	U23
C2	0.0366 (7)	0.0539 (10)	0.0319 (7)	−0.0097 (7)	0.0025 (6)	0.0024 (7)
C3	0.0520 (9)	0.0514 (10)	0.0339 (8)	−0.0129 (8)	0.0044 (7)	0.0047 (7)
C4	0.0391 (7)	0.0485 (10)	0.0291 (7)	−0.0010 (7)	0.0071 (6)	0.0031 (7)
C5	0.0373 (7)	0.0380 (8)	0.0242 (6)	0.0012 (6)	0.0045 (5)	−0.0003 (6)
C6	0.0375 (7)	0.0378 (8)	0.0263 (7)	0.0009 (6)	−0.0004 (5)	−0.0011 (7)
C7	0.0325 (7)	0.0471 (10)	0.0345 (8)	0.0000 (7)	0.0057 (6)	0.0001 (7)
C8	0.0631 (11)	0.0518 (11)	0.0482 (10)	−0.0164 (9)	0.0025 (8)	0.0130 (9)
C9	0.0532 (9)	0.0700 (13)	0.0378 (9)	−0.0141 (10)	0.0116 (7)	0.0122 (9)
C10	0.0545 (9)	0.0477 (10)	0.0290 (7)	−0.0050 (8)	0.0129 (6)	−0.0009 (7)
C11	0.0544 (9)	0.0563 (10)	0.0271 (7)	−0.0143 (9)	−0.0026 (6)	0.0087 (8)
N1	0.0407 (7)	0.0506 (8)	0.0255 (6)	−0.0095 (6)	−0.0019 (5)	0.0053 (6)
O1	0.0721 (8)	0.0765 (10)	0.0357 (6)	−0.0308 (8)	−0.0011 (6)	−0.0067 (7)
O2	0.0583 (7)	0.0559 (8)	0.0275 (6)	−0.0166 (6)	−0.0082 (5)	0.0040 (6)
O3	0.0619 (7)	0.0427 (7)	0.0362 (6)	−0.0111 (6)	0.0053 (5)	0.0005 (6)

C2—O1	1.218 (2)	C7—C10	1.531 (2)
C2—N1	1.347 (2)	C7—H7A	0.9800
C2—C3	1.520 (2)	C8—O3	1.447 (2)
C3—C4	1.517 (3)	C8—C9	1.519 (3)
C3—H3B	0.9700	C8—H8B	0.9700
C3—H3A	0.9700	C8—H8A	0.9700
C4—C5	1.530 (2)	C9—C10	1.531 (3)
C4—H4B	0.9700	C9—H9B	0.9700
C4—H4A	0.9700	C9—H9A	0.9700
C5—N1	1.4591 (18)	C10—C11	1.527 (2)
C5—C6	1.5204 (19)	C10—H10A	0.9800
C5—H5A	0.9800	C11—N1	1.453 (2)
C6—O2	1.4238 (17)	C11—H11B	0.9700
C6—C7	1.510 (2)	C11—H11A	0.9700
C6—H6A	0.9800	O2—H2A	0.82 (3)
C7—O3	1.433 (2)
O1—C2—N1	125.45 (17)	C6—C7—H7A	108.9
O1—C2—C3	126.54 (18)	C10—C7—H7A	108.9
N1—C2—C3	108.00 (15)	O3—C8—C9	106.96 (17)
C4—C3—C2	104.81 (15)	O3—C8—H8B	110.3
C4—C3—H3B	110.8	C9—C8—H8B	110.3
C2—C3—H3B	110.8	O3—C8—H8A	110.3
C4—C3—H3A	110.8	C9—C8—H8A	110.3
C2—C3—H3A	110.8	H8B—C8—H8A	108.6
H3B—C3—H3A	108.9	C8—C9—C10	103.06 (14)
C3—C4—C5	104.93 (12)	C8—C9—H9B	111.2
C3—C4—H4B	110.8	C10—C9—H9B	111.2
C5—C4—H4B	110.8	C8—C9—H9A	111.2
C3—C4—H4A	110.8	C10—C9—H9A	111.2
C5—C4—H4A	110.8	H9B—C9—H9A	109.1
H4B—C4—H4A	108.8	C11—C10—C9	110.32 (16)
N1—C5—C6	108.57 (12)	C11—C10—C7	111.95 (13)
N1—C5—C4	103.15 (13)	C9—C10—C7	100.16 (14)
C6—C5—C4	114.91 (13)	C11—C10—H10A	111.3
N1—C5—H5A	110.0	C9—C10—H10A	111.3
C6—C5—H5A	110.0	C7—C10—H10A	111.3
C4—C5—H5A	110.0	N1—C11—C10	110.56 (13)
O2—C6—C7	108.67 (13)	N1—C11—H11B	109.5
O2—C6—C5	111.18 (13)	C10—C11—H11B	109.5
C7—C6—C5	111.84 (12)	N1—C11—H11A	109.5
O2—C6—H6A	108.4	C10—C11—H11A	109.5
C7—C6—H6A	108.4	H11B—C11—H11A	108.1
C5—C6—H6A	108.4	C2—N1—C11	124.84 (15)
O3—C7—C6	110.87 (13)	C2—N1—C5	114.01 (14)
O3—C7—C10	104.17 (14)	C11—N1—C5	118.47 (13)
C6—C7—C10	114.99 (13)	C6—O2—H2A	110.8 (18)
O3—C7—H7A	108.9	C7—O3—C8	108.27 (13)
O1—C2—C3—C4	−171.33 (18)	O3—C7—C10—C9	41.27 (16)
N1—C2—C3—C4	9.79 (19)	C6—C7—C10—C9	162.80 (14)
C2—C3—C4—C5	−19.80 (18)	C9—C10—C11—N1	−156.02 (15)
C3—C4—C5—N1	22.25 (17)	C7—C10—C11—N1	−45.4 (2)
C3—C4—C5—C6	−95.73 (16)	O1—C2—N1—C11	−12.7 (3)
N1—C5—C6—O2	173.44 (14)	C3—C2—N1—C11	166.20 (16)
C4—C5—C6—O2	−71.68 (18)	O1—C2—N1—C5	−173.78 (17)
N1—C5—C6—C7	51.76 (17)	C3—C2—N1—C5	5.11 (19)
C4—C5—C6—C7	166.64 (13)	C10—C11—N1—C2	−105.48 (18)
O2—C6—C7—O3	−54.82 (17)	C10—C11—N1—C5	54.8 (2)
C5—C6—C7—O3	68.30 (16)	C6—C5—N1—C2	104.77 (16)
O2—C6—C7—C10	−172.63 (14)	C4—C5—N1—C2	−17.57 (17)
C5—C6—C7—C10	−49.52 (19)	C6—C5—N1—C11	−57.6 (2)
O3—C8—C9—C10	19.3 (2)	C4—C5—N1—C11	−179.96 (15)
C8—C9—C10—C11	82.07 (18)	C6—C7—O3—C8	−154.92 (13)
C8—C9—C10—C7	−36.05 (18)	C10—C7—O3—C8	−30.69 (17)
O3—C7—C10—C11	−75.64 (18)	C9—C8—O3—C7	7.04 (19)
C6—C7—C10—C11	45.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3i	0.82 (3)	2.15 (3)	2.9233 (19)	157 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3i	0.82 (3)	2.15 (3)	2.9233 (19)	157 (2)

Symmetry code: (i) .