(R)-(-)-3-Hydroxy-quinuclidinium chloride.

The quinuclidinium cation of the title compound, C(7)H(14)NO(+)·Cl(-), shows a twist along the C-N pseudo-threefold axis, with N-C-C-C torsion angles of -16.0 (1), -16.9 (1) and -15.6 (1)°. The crystal structure is stabilized by N-H⋯Cl and O-H⋯Cl hydrogen bonds, forming infinite chains along the a and b axes.

Related literature

For related literature see: Carroll et al. (1991 ▶); Erman et al. (1994 ▶); Frackenpohl & Hoffmann (2000 ▶); Bosak et al. (2005 ▶); Lis & Jeżowska-Trzebiatowska (1976 ▶); Lis et al. (1975 ▶); Morrow (1962 ▶); Noddack & Noddack (1933 ▶); Sterling et al. (1988 ▶).

Experimental

Crystal data

C7H14NO+·Cl−

M = 163.64

Tetragonal,

a = 6.655 (3) Å

c = 18.145 (9) Å

V = 803.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 100 (2) K

0.50 × 0.34 × 0.08 mm

Data collection

Kuma KM-4 CCD κ-geometry diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.86, T max = 0.97

11241 measured reflections

3310 independent reflections

3128 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.063

S = 1.00

3310 reflections

92 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1361 Friedel pairs

Flack parameter: −0.01 (3)

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data n class="Disease">reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009185/pk2091sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009185/pk2091Isup2.hkl

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

C7H14NO+·Cl–	Z = 4
Mr = 163.64	F000 = 352
Tetragonal, P41	Dx = 1.353 Mg m−3
Hall symbol: P 4w	Mo Kα radiation λ = 0.71073 Å
a = 6.655 (3) Å	Cell parameters from 11099 reflections
b = 6.655 (3) Å	θ = 3.3–36.6º
c = 18.145 (9) Å	µ = 0.41 mm−1
α = 90º	T = 100 (2) K
β = 90º	Plate, colorless
γ = 90º	0.50 × 0.34 × 0.08 mm
V = 803.6 (6) Å3

Kuma KM-4-CCD κ-geometry diffractometer	3310 independent reflections
Radiation source: medium-focus sealed tube	3128 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
T = 100(2) K	θmax = 36.7º
ω scans	θmin = 3.3º
Absorption correction: analytical(CrysAlis RED; Oxford Diffraction, 2007)	h = −11→8
Tmin = 0.86, Tmax = 0.97	k = −8→11
11241 measured reflections	l = −23→30

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.026	w = 1/[σ2(Fo2) + (0.0453P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.063	(Δ/σ)max = 0.001
S = 1.00	Δρmax = 0.36 e Å−3
3310 reflections	Δρmin = −0.20 e Å−3
92 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 1261 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (3)
Secondary atom site location: difference Fourier map

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
Cl	0.85575 (3)	0.53610 (3)	0.500252 (12)	0.01541 (5)
O1	0.08282 (10)	0.92929 (11)	0.46762 (4)	0.01799 (13)
H11	0.0253	0.8180	0.4732	0.027*
N1	0.56591 (11)	0.89016 (11)	0.51704 (4)	0.01256 (13)
H1	0.6593	0.7862	0.5167	0.015*
C2	0.36697 (13)	0.80978 (13)	0.54256 (5)	0.01451 (15)
H21	0.3745	0.7744	0.5955	0.017*
H22	0.3327	0.6869	0.5145	0.017*
C3	0.20359 (12)	0.97096 (13)	0.53048 (5)	0.01341 (14)
H3	0.1163	0.9797	0.5752	0.016*
C4	0.30861 (12)	1.17237 (13)	0.51807 (5)	0.01337 (14)
H4	0.2084	1.2843	0.5185	0.016*
C5	0.46336 (13)	1.20182 (13)	0.57991 (5)	0.01436 (15)
H52	0.3990	1.1795	0.6284	0.017*
H51	0.5161	1.3409	0.5787	0.017*
C6	0.63647 (13)	1.05125 (14)	0.56902 (5)	0.01397 (15)
H61	0.7553	1.1206	0.5483	0.017*
H62	0.6748	0.9912	0.6169	0.017*
C7	0.54836 (14)	0.97482 (14)	0.44064 (5)	0.01571 (16)
H71	0.4843	0.8753	0.4076	0.019*
H72	0.6835	1.0064	0.4210	0.019*
C8	0.42035 (14)	1.16677 (14)	0.44410 (5)	0.01546 (15)
H82	0.5077	1.2865	0.4394	0.019*
H81	0.3226	1.1680	0.4030	0.019*

	U11	U22	U33	U12	U13	U23
Cl	0.01498 (9)	0.01326 (9)	0.01800 (9)	0.00201 (7)	0.00182 (7)	0.00096 (7)
O1	0.0151 (3)	0.0194 (3)	0.0195 (3)	−0.0034 (2)	−0.0051 (2)	−0.0014 (2)
N1	0.0121 (3)	0.0123 (3)	0.0133 (3)	0.0018 (2)	0.0001 (2)	0.0000 (2)
C2	0.0139 (3)	0.0126 (3)	0.0171 (4)	−0.0022 (3)	−0.0003 (3)	0.0018 (3)
C3	0.0103 (3)	0.0151 (3)	0.0149 (3)	−0.0010 (3)	−0.0001 (3)	−0.0015 (3)
C4	0.0122 (3)	0.0112 (3)	0.0167 (4)	0.0016 (2)	−0.0018 (3)	−0.0008 (3)
C5	0.0136 (3)	0.0137 (3)	0.0157 (4)	0.0002 (3)	−0.0010 (3)	−0.0024 (3)
C6	0.0125 (3)	0.0148 (3)	0.0146 (4)	−0.0001 (3)	−0.0027 (3)	−0.0011 (3)
C7	0.0165 (4)	0.0195 (4)	0.0111 (3)	0.0023 (3)	0.0017 (3)	0.0007 (3)
C8	0.0158 (4)	0.0163 (4)	0.0143 (4)	0.0005 (3)	−0.0013 (3)	0.0034 (3)

O1—C3	1.4227 (11)	C4—C5	1.5355 (13)
O1—H11	0.8400	C4—H4	1.0000
N1—C7	1.5009 (13)	C5—C6	1.5396 (13)
N1—C2	1.5011 (12)	C5—H52	0.9900
N1—C6	1.5031 (12)	C5—H51	0.9900
N1—H1	0.9300	C6—H61	0.9900
C2—C3	1.5430 (13)	C6—H62	0.9900
C2—H21	0.9900	C7—C8	1.5367 (14)
C2—H22	0.9900	C7—H71	0.9900
C3—C4	1.5284 (13)	C7—H72	0.9900
C3—H3	1.0000	C8—H82	0.9900
C4—C8	1.5349 (14)	C8—H81	0.9900
C3—O1—H11	109.5	C4—C5—C6	108.97 (7)
C7—N1—C2	110.49 (7)	C4—C5—H52	109.9
C7—N1—C6	109.64 (7)	C6—C5—H52	109.9
C2—N1—C6	109.64 (7)	C4—C5—H51	109.9
C7—N1—H1	109.0	C6—C5—H51	109.9
C2—N1—H1	109.0	H52—C5—H51	108.3
C6—N1—H1	109.0	N1—C6—C5	108.12 (6)
N1—C2—C3	109.27 (7)	N1—C6—H61	110.1
N1—C2—H21	109.8	C5—C6—H61	110.1
C3—C2—H21	109.8	N1—C6—H62	110.1
N1—C2—H22	109.8	C5—C6—H62	110.1
C3—C2—H22	109.8	H61—C6—H62	108.4
H21—C2—H22	108.3	N1—C7—C8	108.51 (7)
O1—C3—C4	108.13 (7)	N1—C7—H71	110.0
O1—C3—C2	112.11 (7)	C8—C7—H71	110.0
C4—C3—C2	107.96 (7)	N1—C7—H72	110.0
O1—C3—H3	109.5	C8—C7—H72	110.0
C4—C3—H3	109.5	H71—C7—H72	108.4
C2—C3—H3	109.5	C4—C8—C7	108.93 (7)
C3—C4—C8	109.21 (7)	C4—C8—H82	109.9
C3—C4—C5	108.12 (7)	C7—C8—H82	109.9
C8—C4—C5	108.49 (8)	C4—C8—H81	109.9
C3—C4—H4	110.3	C7—C8—H81	109.9
C8—C4—H4	110.3	H82—C8—H81	108.3
C5—C4—H4	110.3
C7—N1—C2—C3	−50.50 (9)	C8—C4—C5—C6	−48.56 (9)
C6—N1—C2—C3	70.45 (9)	C7—N1—C6—C5	71.20 (8)
N1—C2—C3—O1	102.96 (9)	C2—N1—C6—C5	−50.27 (9)
N1—C2—C3—C4	−16.03 (9)	C4—C5—C6—N1	−16.88 (9)
O1—C3—C4—C8	−53.44 (9)	C2—N1—C7—C8	69.13 (9)
C2—C3—C4—C8	68.06 (9)	C6—N1—C7—C8	−51.82 (9)
O1—C3—C4—C5	−171.30 (7)	C3—C4—C8—C7	−49.82 (9)
C2—C3—C4—C5	−49.80 (9)	C5—C4—C8—C7	67.81 (9)
C3—C4—C5—C6	69.77 (9)	N1—C7—C8—C4	−15.62 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl	0.93	2.14	3.060 (2)	171
O1—H11···Cli	0.84	2.24	3.079 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl	0.93	2.14	3.060 (2)	171
O1—H11⋯Cli	0.84	2.24	3.079 (2)	173

Symmetry code: (i) .