(4R,6S,7S,8S,8aS)-6-Ethyl-7,8-dihy-droxy-4-methyl-1,2,3,5,6,7,8,8a-octa-hydro-indolizin-4-ium iodide.

The title compound, C(11)H(22)NO(2) (+)·I(-), is a chiral mol-ecule with five stereogenic centres. The absolute configuration was assigned from the synthesis and confirmed by the structure determination. The central six-membered ring of the indolizine system adopts a chair conformation, with two atoms displaced by -0.690 (2) and 0.550 (2) Å from the plane of the other four atoms. The conformation of the pyrrolidine ring is close to that of an envelope, with the flap atom displaced by 0.563 (2) Å from the plane of the remaining four atoms. In the crystal, there are two O-H⋯I hydrogen bonds.

Related literature

For the biological activity of indolizine derivatives, see: Gubin et al. (1992 ▶); Gupta et al. (2003 ▶); Malonne et al. (1998 ▶); Medda et al. (2003 ▶); Nardelli (1983 ▶); Pearson & Guo (2001 ▶); Ruprecht et al. (1989 ▶). For puckering analysis, see: Cremer & Pople (1975 ▶). For the preparation, see: Šafář et al. (2010 ▶). For related structures, see: Clark & Reid (1995 ▶); Pedersen (1967 ▶).

Experimental

Crystal data

C11H22NO2 +·I−

M = 327.20

Monoclinic,

a = 8.18603 (14) Å

b = 10.82977 (14) Å

c = 8.19874 (13) Å

β = 110.3688 (19)°

V = 681.39 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.34 mm−1

T = 298 K

0.30 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.520, T max = 0.638

18648 measured reflections

3330 independent reflections

3176 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.049

S = 0.91

3330 reflections

141 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.69 e Å−3

Absolute structure: Flack (1983 ▶), 1359 Friedel pairs

Flack parameter: −0.026 (17)

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811051099/bq2323sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051099/bq2323Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051099/bq2323Isup3.cml

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

C11H22NO2+·I−	F(000) = 328
Mr = 327.20	Dx = 1.595 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3330 reflections
a = 8.18603 (14) Å	θ = 3.6–29.4°
b = 10.82977 (14) Å	µ = 2.34 mm−1
c = 8.19874 (13) Å	T = 298 K
β = 110.3688 (19)°	Prism, colourless
V = 681.39 (2) Å3	0.30 × 0.25 × 0.20 mm
Z = 2

Oxford Diffraction Gemini R CCD diffractometer	3330 independent reflections
Radiation source: fine-focus sealed tube	3176 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 10.434 pixels mm-1	θmax = 29.4°, θmin = 3.6°
ω and φ scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −14→14
Tmin = 0.520, Tmax = 0.638	l = −11→10
18648 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.019	w = 1/[σ2(Fo2) + (0.0335P)2 + 0.2787P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.049	(Δ/σ)max < 0.001
S = 0.91	Δρmax = 0.64 e Å−3
3330 reflections	Δρmin = −0.69 e Å−3
141 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.044 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1359 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.026 (17)

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	0.5506 (4)	0.1519 (3)	0.1098 (4)	0.0581 (7)
H2A	0.4507	0.2056	0.0599	0.070*
H2B	0.6055	0.1385	0.0237	0.070*
C3	0.4953 (5)	0.0317 (3)	0.1635 (5)	0.0735 (9)
H3A	0.5487	−0.0365	0.1238	0.088*
H3B	0.3697	0.0229	0.1134	0.088*
C4	0.5545 (4)	0.0321 (3)	0.3627 (4)	0.0538 (6)
H4A	0.4590	0.0099	0.4012	0.065*
H4B	0.6495	−0.0256	0.4122	0.065*
C5	0.6143 (3)	0.1645 (2)	0.4157 (3)	0.0376 (4)
H5	0.5115	0.2133	0.4092	0.045*
C6	0.7478 (3)	0.1787 (2)	0.5989 (3)	0.0358 (4)
H6	0.7088	0.1294	0.6787	0.043*
C7	0.9331 (3)	0.13766 (19)	0.6181 (3)	0.0336 (4)
H7	1.0133	0.1641	0.7321	0.040*
C8	0.9902 (3)	0.19544 (19)	0.4777 (3)	0.0340 (4)
H8	0.9914	0.2854	0.4913	0.041*
C9	0.8601 (3)	0.1627 (2)	0.2992 (3)	0.0395 (5)
H9A	0.8994	0.1978	0.2103	0.047*
H9B	0.8562	0.0737	0.2853	0.047*
C10	0.6736 (4)	0.3470 (2)	0.2554 (4)	0.0565 (7)
H10A	0.7083	0.3703	0.1592	0.085*
H10B	0.7517	0.3834	0.3603	0.085*
H10C	0.5572	0.3757	0.2352	0.085*
C11	1.1720 (3)	0.1536 (3)	0.4865 (3)	0.0477 (6)
H11A	1.1688	0.0662	0.4598	0.057*
H11B	1.2044	0.1977	0.3994	0.057*
C12	1.3095 (3)	0.1765 (3)	0.6658 (4)	0.0586 (7)
H12A	1.4233	0.1615	0.6611	0.088*
H12B	1.2894	0.1220	0.7492	0.088*
H12C	1.3020	0.2606	0.6998	0.088*
N1	0.6791 (2)	0.20968 (18)	0.2730 (2)	0.0373 (4)
O1	0.7466 (2)	0.30534 (17)	0.6448 (3)	0.0537 (5)
H1	0.8265	0.3185	0.7367	0.080*
O2	0.9442 (2)	0.00727 (14)	0.6053 (2)	0.0444 (4)
H2	0.9405	−0.0249	0.6945	0.067*
I1	0.11548 (2)	0.38255 (2)	0.028309 (17)	0.05615 (7)

	U11	U22	U33	U12	U13	U23
C2	0.0441 (13)	0.079 (2)	0.0373 (12)	−0.0013 (13)	−0.0032 (10)	−0.0131 (12)
C3	0.0651 (18)	0.070 (2)	0.072 (2)	−0.0226 (16)	0.0065 (16)	−0.0302 (17)
C4	0.0494 (13)	0.0441 (13)	0.0663 (17)	−0.0150 (11)	0.0180 (12)	−0.0109 (12)
C5	0.0291 (9)	0.0385 (10)	0.0444 (12)	−0.0017 (8)	0.0118 (8)	−0.0050 (9)
C6	0.0329 (9)	0.0395 (11)	0.0371 (10)	0.0043 (8)	0.0150 (8)	−0.0039 (9)
C7	0.0351 (10)	0.0352 (10)	0.0304 (10)	0.0048 (8)	0.0112 (8)	0.0018 (8)
C8	0.0288 (9)	0.0361 (10)	0.0351 (10)	0.0007 (8)	0.0088 (8)	0.0050 (8)
C9	0.0354 (10)	0.0501 (12)	0.0321 (10)	0.0021 (9)	0.0107 (8)	0.0033 (9)
C10	0.0488 (13)	0.0441 (14)	0.0606 (15)	0.0033 (9)	−0.0011 (11)	0.0162 (10)
C11	0.0309 (10)	0.0685 (17)	0.0435 (13)	0.0013 (10)	0.0127 (10)	0.0097 (11)
C12	0.0313 (11)	0.082 (2)	0.0570 (16)	−0.0028 (12)	0.0086 (11)	0.0059 (15)
N1	0.0317 (8)	0.0411 (9)	0.0318 (9)	−0.0007 (7)	0.0017 (7)	0.0010 (7)
O1	0.0487 (10)	0.0491 (10)	0.0534 (10)	0.0136 (8)	0.0054 (8)	−0.0195 (8)
O2	0.0575 (10)	0.0344 (8)	0.0492 (10)	0.0114 (7)	0.0286 (8)	0.0114 (7)
I1	0.06754 (11)	0.06164 (10)	0.04070 (9)	−0.00802 (11)	0.02063 (6)	−0.01043 (10)

C2—C3	1.494 (5)	C8—C9	1.522 (3)
C2—N1	1.520 (3)	C8—C11	1.533 (3)
C2—H2A	0.9700	C8—H8	0.9800
C2—H2B	0.9700	C9—N1	1.510 (3)
C3—C4	1.533 (5)	C9—H9A	0.9700
C3—H3A	0.9700	C9—H9B	0.9700
C3—H3B	0.9700	C10—N1	1.493 (3)
C4—C5	1.528 (3)	C10—H10A	0.9600
C4—H4A	0.9700	C10—H10B	0.9600
C4—H4B	0.9700	C10—H10C	0.9600
C5—N1	1.523 (3)	C11—C12	1.529 (4)
C5—C6	1.527 (3)	C11—H11A	0.9700
C5—H5	0.9800	C11—H11B	0.9700
C6—O1	1.423 (3)	C12—H12A	0.9600
C6—C7	1.535 (3)	C12—H12B	0.9600
C6—H6	0.9800	C12—H12C	0.9600
C7—O2	1.421 (3)	O1—H1	0.8200
C7—C8	1.519 (3)	O2—H2	0.8200
C7—H7	0.9800
C3—C2—N1	106.7 (2)	C7—C8—C11	113.04 (18)
C3—C2—H2A	110.4	C9—C8—C11	108.61 (19)
N1—C2—H2A	110.4	C7—C8—H8	108.5
C3—C2—H2B	110.4	C9—C8—H8	108.5
N1—C2—H2B	110.4	C11—C8—H8	108.5
H2A—C2—H2B	108.6	N1—C9—C8	112.42 (18)
C2—C3—C4	107.2 (2)	N1—C9—H9A	109.1
C2—C3—H3A	110.3	C8—C9—H9A	109.1
C4—C3—H3A	110.3	N1—C9—H9B	109.1
C2—C3—H3B	110.3	C8—C9—H9B	109.1
C4—C3—H3B	110.3	H9A—C9—H9B	107.9
H3A—C3—H3B	108.5	N1—C10—H10A	109.5
C5—C4—C3	104.9 (2)	N1—C10—H10B	109.5
C5—C4—H4A	110.8	H10A—C10—H10B	109.5
C3—C4—H4A	110.8	N1—C10—H10C	109.5
C5—C4—H4B	110.8	H10A—C10—H10C	109.5
C3—C4—H4B	110.8	H10B—C10—H10C	109.5
H4A—C4—H4B	108.8	C12—C11—C8	112.0 (2)
N1—C5—C6	113.69 (17)	C12—C11—H11A	109.2
N1—C5—C4	104.21 (19)	C8—C11—H11A	109.2
C6—C5—C4	115.0 (2)	C12—C11—H11B	109.2
N1—C5—H5	107.9	C8—C11—H11B	109.2
C6—C5—H5	107.9	H11A—C11—H11B	107.9
C4—C5—H5	107.9	C11—C12—H12A	109.5
O1—C6—C5	106.78 (18)	C11—C12—H12B	109.5
O1—C6—C7	110.46 (18)	H12A—C12—H12B	109.5
C5—C6—C7	114.51 (17)	C11—C12—H12C	109.5
O1—C6—H6	108.3	H12A—C12—H12C	109.5
C5—C6—H6	108.3	H12B—C12—H12C	109.5
C7—C6—H6	108.3	C10—N1—C9	110.1 (2)
O2—C7—C8	108.01 (17)	C10—N1—C2	109.6 (2)
O2—C7—C6	111.47 (18)	C9—N1—C2	109.31 (19)
C8—C7—C6	110.88 (17)	C10—N1—C5	112.8 (2)
O2—C7—H7	108.8	C9—N1—C5	111.69 (16)
C8—C7—H7	108.8	C2—N1—C5	103.01 (19)
C6—C7—H7	108.8	C6—O1—H1	109.5
C7—C8—C9	109.65 (17)	C7—O2—H2	109.5
N1—C2—C3—C4	13.6 (3)	C7—C8—C9—N1	60.6 (2)
C2—C3—C4—C5	10.0 (3)	C11—C8—C9—N1	−175.43 (19)
C3—C4—C5—N1	−29.6 (3)	C7—C8—C11—C12	−54.9 (3)
C3—C4—C5—C6	−154.8 (2)	C9—C8—C11—C12	−176.8 (2)
N1—C5—C6—O1	77.7 (2)	C8—C9—N1—C10	71.0 (2)
C4—C5—C6—O1	−162.2 (2)	C8—C9—N1—C2	−168.5 (2)
N1—C5—C6—C7	−44.9 (3)	C8—C9—N1—C5	−55.1 (2)
C4—C5—C6—C7	75.2 (3)	C3—C2—N1—C10	−152.2 (3)
O1—C6—C7—O2	168.90 (18)	C3—C2—N1—C9	87.0 (3)
C5—C6—C7—O2	−70.5 (2)	C3—C2—N1—C5	−31.8 (3)
O1—C6—C7—C8	−70.7 (2)	C6—C5—N1—C10	−78.1 (2)
C5—C6—C7—C8	49.9 (2)	C4—C5—N1—C10	155.86 (19)
O2—C7—C8—C9	66.0 (2)	C6—C5—N1—C9	46.5 (2)
C6—C7—C8—C9	−56.5 (2)	C4—C5—N1—C9	−79.5 (2)
O2—C7—C8—C11	−55.4 (2)	C6—C5—N1—C2	163.7 (2)
C6—C7—C8—C11	−177.79 (19)	C4—C5—N1—C2	37.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···I1i	0.82	2.80	3.6187 (18)	173.
O2—H2···I1ii	0.82	2.67	3.4798 (16)	172.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯I1i	0.82	2.80	3.6187 (18)	173
O2—H2⋯I1ii	0.82	2.67	3.4798 (16)	172

Symmetry codes: (i) ; (ii) .