(6S,7S,8R,8aS)-6-Ethyl-perhydro-indolizine-7,8-diol.

In the title compound, C(10)H(19)NO(2), the piperidine and pyrrolidine rings of the perhydro-indolizine ring system adopt chair and envelope conformations, respectively. In the crystal structure, inter-molecular O-H⋯N and O-H⋯O hydrogen bonds link the mol-ecules into a chain running along the a axis.

Related literature

For indolizine derivatives, see: Bermudez et al. (1990 ▶); Bonneau et al. (2003 ▶); Chai et al. (2003 ▶); Delattre et al. (2005 ▶); Gundersen et al. (2007 ▶); Liu et al. (2007 ▶); Teklu et al. (2005 ▶); Weide et al. (2006 ▶). For ring conformations, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶). For the synthesis, see: Šafař et al. (2010 ▶).

Experimental

Crystal data

C10H19NO2

M = 185.26

Orthorhombic,

a = 7.20849 (17) Å

b = 8.83039 (19) Å

c = 15.6656 (4) Å

V = 997.18 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.51 × 0.29 × 0.09 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical (Clark & Reid, 1995 ▶) T min = 0.950, T max = 0.992

26407 measured reflections

1554 independent reflections

1371 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.099

S = 1.07

1554 reflections

124 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.18 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 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021240/is2552sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021240/is2552Isup2.hkl

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

C10H19NO2	F(000) = 408
Mr = 185.26	Dx = 1.234 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 17389 reflections
a = 7.20849 (17) Å	θ = 3.5–29.5°
b = 8.83039 (19) Å	µ = 0.09 mm−1
c = 15.6656 (4) Å	T = 298 K
V = 997.18 (4) Å3	Prism, white
Z = 4	0.51 × 0.29 × 0.09 mm

Oxford Diffraction Gemini R CCD diffractometer	1554 independent reflections
Radiation source: fine-focus sealed tube	1371 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 10.4340 pixels mm-1	θmax = 29.5°, θmin = 3.5°
Rotation method data acquisition using ω and φ scans	h = −9→9
Absorption correction: analytical (Clark & Reid, 1995)	k = −11→12
Tmin = 0.950, Tmax = 0.992	l = −21→20
26407 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0669P)2 + 0.0442P] where P = (Fo2 + 2Fc2)/3
1554 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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

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
C2	0.3886 (2)	0.5154 (2)	0.85244 (11)	0.0478 (4)
H2B	0.2624	0.5248	0.8732	0.057*
H2A	0.4043	0.4161	0.8270	0.057*
C3	0.4326 (2)	0.6396 (3)	0.78828 (12)	0.0544 (5)
H3B	0.3442	0.7220	0.7931	0.065*
H3A	0.4284	0.6003	0.7305	0.065*
C4	0.6291 (2)	0.6945 (2)	0.81031 (10)	0.0424 (4)
H4B	0.7087	0.6928	0.7604	0.051*
H4A	0.6266	0.7964	0.8334	0.051*
C5	0.69456 (19)	0.58078 (16)	0.87717 (9)	0.0311 (3)
H5A	0.7393	0.4907	0.8470	0.037*
C6	0.84249 (18)	0.62711 (14)	0.94069 (9)	0.0277 (3)
H6A	0.9566	0.6503	0.9093	0.033*
C7	0.8790 (2)	0.49092 (15)	0.99892 (9)	0.0314 (3)
H7A	0.9272	0.4098	0.9624	0.038*
C8	0.7028 (2)	0.42864 (16)	1.04186 (10)	0.0346 (3)
H8A	0.7353	0.3283	1.0640	0.042*
C9	0.5529 (2)	0.40321 (17)	0.97423 (11)	0.0393 (4)
H9B	0.5893	0.3199	0.9375	0.047*
H9A	0.4376	0.3756	1.0021	0.047*
C10	0.6369 (2)	0.52143 (19)	1.11850 (10)	0.0401 (4)
H10B	0.7403	0.5354	1.1573	0.048*
H10A	0.5987	0.6207	1.0987	0.048*
C11	0.4772 (3)	0.4499 (3)	1.16706 (12)	0.0624 (6)
H11C	0.4429	0.5140	1.2140	0.075*
H11B	0.5147	0.3527	1.1884	0.075*
H11A	0.3730	0.4377	1.1295	0.075*
N1	0.52295 (16)	0.53891 (14)	0.92216 (8)	0.0319 (3)
O1	0.78542 (14)	0.75959 (11)	0.98549 (6)	0.0301 (2)
H1A	0.869 (3)	0.7981 (19)	1.0102 (12)	0.036*
O12	1.01533 (16)	0.51868 (14)	1.06187 (8)	0.0450 (3)
H12A	1.085 (3)	0.582 (2)	1.0417 (14)	0.054*

	U11	U22	U33	U12	U13	U23
C2	0.0338 (7)	0.0584 (10)	0.0512 (9)	−0.0026 (8)	−0.0100 (7)	−0.0214 (8)
C3	0.0466 (9)	0.0696 (12)	0.0471 (9)	0.0076 (9)	−0.0156 (8)	−0.0088 (9)
C4	0.0475 (9)	0.0487 (8)	0.0310 (7)	0.0031 (8)	−0.0053 (7)	−0.0016 (6)
C5	0.0280 (6)	0.0318 (6)	0.0334 (6)	0.0016 (6)	0.0015 (5)	−0.0074 (5)
C6	0.0237 (6)	0.0254 (6)	0.0341 (6)	−0.0005 (5)	0.0016 (5)	−0.0009 (5)
C7	0.0242 (6)	0.0264 (6)	0.0437 (8)	0.0013 (5)	0.0007 (5)	0.0006 (5)
C8	0.0282 (7)	0.0241 (6)	0.0515 (8)	0.0003 (6)	0.0022 (6)	0.0072 (6)
C9	0.0323 (7)	0.0281 (7)	0.0575 (9)	−0.0072 (6)	0.0030 (7)	−0.0038 (6)
C10	0.0360 (7)	0.0458 (8)	0.0385 (7)	0.0043 (7)	0.0019 (6)	0.0102 (6)
C11	0.0378 (8)	0.0995 (16)	0.0500 (9)	0.0001 (10)	0.0066 (8)	0.0219 (11)
N1	0.0242 (5)	0.0326 (6)	0.0387 (6)	−0.0031 (5)	−0.0028 (5)	−0.0084 (5)
O1	0.0274 (5)	0.0244 (4)	0.0385 (5)	−0.0001 (4)	−0.0056 (4)	−0.0038 (4)
O12	0.0305 (6)	0.0498 (7)	0.0548 (7)	−0.0060 (5)	−0.0097 (5)	0.0156 (6)

C2—N1	1.4742 (18)	C7—C8	1.5386 (19)
C2—C3	1.521 (3)	C7—H7A	0.9800
C2—H2B	0.9700	C8—C10	1.529 (2)
C2—H2A	0.9700	C8—C9	1.530 (2)
C3—C4	1.536 (2)	C8—H8A	0.9800
C3—H3B	0.9700	C9—N1	1.465 (2)
C3—H3A	0.9700	C9—H9B	0.9700
C4—C5	1.526 (2)	C9—H9A	0.9700
C4—H4B	0.9700	C10—C11	1.518 (2)
C4—H4A	0.9700	C10—H10B	0.9700
C5—N1	1.4710 (17)	C10—H10A	0.9700
C5—C6	1.5148 (18)	C11—H11C	0.9600
C5—H5A	0.9800	C11—H11B	0.9600
C6—O1	1.4250 (16)	C11—H11A	0.9600
C6—C7	1.5322 (18)	O1—H1A	0.79 (2)
C6—H6A	0.9800	O12—H12A	0.82 (2)
C7—O12	1.4137 (18)
N1—C2—C3	104.54 (13)	O12—C7—H7A	106.7
N1—C2—H2B	110.8	C6—C7—H7A	106.7
C3—C2—H2B	110.8	C8—C7—H7A	106.7
N1—C2—H2A	110.8	C10—C8—C9	113.74 (12)
C3—C2—H2A	110.8	C10—C8—C7	114.10 (12)
H2B—C2—H2A	108.9	C9—C8—C7	109.43 (12)
C2—C3—C4	105.74 (14)	C10—C8—H8A	106.3
C2—C3—H3B	110.6	C9—C8—H8A	106.3
C4—C3—H3B	110.6	C7—C8—H8A	106.3
C2—C3—H3A	110.6	N1—C9—C8	111.68 (11)
C4—C3—H3A	110.6	N1—C9—H9B	109.3
H3B—C3—H3A	108.7	C8—C9—H9B	109.3
C5—C4—C3	103.41 (15)	N1—C9—H9A	109.3
C5—C4—H4B	111.1	C8—C9—H9A	109.3
C3—C4—H4B	111.1	H9B—C9—H9A	107.9
C5—C4—H4A	111.1	C11—C10—C8	113.97 (15)
C3—C4—H4A	111.1	C11—C10—H10B	108.8
H4B—C4—H4A	109.0	C8—C10—H10B	108.8
N1—C5—C6	110.19 (11)	C11—C10—H10A	108.8
N1—C5—C4	103.54 (12)	C8—C10—H10A	108.8
C6—C5—C4	119.40 (13)	H10B—C10—H10A	107.7
N1—C5—H5A	107.7	C10—C11—H11C	109.5
C6—C5—H5A	107.7	C10—C11—H11B	109.5
C4—C5—H5A	107.7	H11C—C11—H11B	109.5
O1—C6—C5	110.00 (11)	C10—C11—H11A	109.5
O1—C6—C7	113.62 (11)	H11C—C11—H11A	109.5
C5—C6—C7	107.46 (11)	H11B—C11—H11A	109.5
O1—C6—H6A	108.5	C9—N1—C5	110.39 (11)
C5—C6—H6A	108.5	C9—N1—C2	113.21 (12)
C7—C6—H6A	108.5	C5—N1—C2	103.45 (11)
O12—C7—C6	113.49 (11)	C6—O1—H1A	112.0 (13)
O12—C7—C8	109.31 (11)	C7—O12—H12A	106.1 (15)
C6—C7—C8	113.52 (12)
N1—C2—C3—C4	18.32 (17)	O12—C7—C8—C9	178.22 (11)
C2—C3—C4—C5	8.30 (17)	C6—C7—C8—C9	50.40 (15)
C3—C4—C5—N1	−32.09 (15)	C10—C8—C9—N1	76.70 (16)
C3—C4—C5—C6	−154.99 (13)	C7—C8—C9—N1	−52.21 (16)
N1—C5—C6—O1	−63.72 (14)	C9—C8—C10—C11	60.38 (17)
C4—C5—C6—O1	55.85 (16)	C7—C8—C10—C11	−173.12 (12)
N1—C5—C6—C7	60.44 (14)	C8—C9—N1—C5	60.58 (15)
C4—C5—C6—C7	−179.99 (12)	C8—C9—N1—C2	176.00 (12)
O1—C6—C7—O12	−58.02 (16)	C6—C5—N1—C9	−65.22 (14)
C5—C6—C7—O12	−179.95 (11)	C4—C5—N1—C9	165.98 (11)
O1—C6—C7—C8	67.60 (15)	C6—C5—N1—C2	173.37 (12)
C5—C6—C7—C8	−54.33 (14)	C4—C5—N1—C2	44.57 (14)
O12—C7—C8—C10	49.50 (16)	C3—C2—N1—C9	−158.49 (13)
C6—C7—C8—C10	−78.32 (15)	C3—C2—N1—C5	−39.00 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1i	0.79 (2)	2.104 (19)	2.8619 (16)	160.2 (18)
O12—H12A···O1i	0.82 (2)	2.05 (2)	2.8591 (15)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1i	0.79 (2)	2.104 (19)	2.8619 (16)	160.2 (18)
O12—H12A⋯O1i	0.82 (2)	2.05 (2)	2.8591 (15)	169 (2)

Symmetry code: (i) .