(R)-(-)-Quinuclidin-3-ol.

The structure of the title compound [alternatively called (R)-(-)-1-aza-bicyclo-[2.2.2]octan-3-ol], C7H13NO, at 100 K has hexa-gonal (P61) symmetry. The structure shows a twist along the C-N pseudo-threefold axis. In the crystal, mol-ecules are linked via O-H⋯N hydrogen bonds, forming infinite chains along the c-axis direction. The crystal studied was twinned by merohedry (twin law: 010, 100, 00-1; population: 0.925:0.075).

Related literature

The title compound is a key building block for the syntheses of muscarinic receptor ligands, including solifenacin (Naito et al., 2005 ▶), revatropate (Alabaster, 1997 ▶) and talsaclidine (Leusch et al., 2000 ▶). For properties of the title compound, see: Bosak et al. (2005 ▶); Carroll et al. (1991 ▶); Frackenpohl & Hoffmann (2000 ▶); Day & Motherwell (2006 ▶); Malone & Armstrong (2006 ▶); Siczek & Lis (2008 ▶); Sterling et al. (1988 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶); For absolute configuration, see: Flack (1983 ▶); The twin law was determined using TwinRotMat implemented in PLATON (Spek, 2009 ▶).

Experimental

Crystal data

C7H13NO

M = 127.18

Hexagonal,

a = 6.2076 (3) Å

c = 29.8731 (13) Å

V = 996.91 (11) Å3

Z = 6

Cu Kα1 radiation

μ = 0.67 mm−1

T = 100 K

0.58 × 0.44 × 0.32 mm

Data collection

Bruker D8 VENTURE diffractometer

Absorption correction: numerical (SADABS; Bruker, 2012 ▶) T min = 0.58, T max = 0.74

15447 measured reflections

1240 independent reflections

1240 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.064

S = 1.15

1240 reflections

85 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.12 e Å−3

Absolute structure: Parsons & Flack (2004 ▶).

Absolute structure parameter: 0.01 (4)

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813026998/bg2517sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026998/bg2517Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813026998/bg2517Isup3.cml

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

C7H13NO	Dx = 1.271 Mg m−3
Mr = 127.18	Melting point: 492(2) K
Hexagonal, P61	Cu Kα1 radiation, λ = 1.54178 Å
a = 6.2076 (3) Å	µ = 0.67 mm−1
c = 29.8731 (13) Å	T = 100 K
V = 996.91 (11) Å3	Prism, clear light colourless
Z = 6	0.58 × 0.44 × 0.32 mm
F(000) = 420

Bruker D8 VENTURE diffractometer	1240 independent reflections
Radiation source: sealed X-ray tube, high brilliance microfocus sealed tube, Cu	1240 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 1024 x 1024 pixels mm-1	θmax = 69.2°, θmin = 4.4°
φ and ω scans	h = −7→7
Absorption correction: numerical (SADABS; Bruker, 2012)	k = −7→7
Tmin = 0.58, Tmax = 0.74	l = −34→35
15447 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.023	w = 1/[σ2(Fo2) + (0.0394P)2 + 0.1183P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.064	(Δ/σ)max < 0.001
S = 1.15	Δρmax = 0.23 e Å−3
1240 reflections	Δρmin = −0.12 e Å−3
85 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0156 (15)
0 constraints	Absolute structure: Parsons & Flack (2004).
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (4)

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. Refined as a 2-component twin.

	x	y	z	Uiso*/Ueq
O1	−0.1928 (2)	0.4528 (2)	0.48963 (4)	0.0175 (3)
H1	−0.2253	0.4264	0.4622	0.026*
N1	0.3057 (3)	0.6832 (3)	0.56404 (5)	0.0157 (4)
C2	0.5095 (3)	0.8018 (3)	0.48879 (6)	0.0166 (4)
H2A	0.5325	0.9500	0.4722	0.020*
H2B	0.6378	0.7625	0.4786	0.020*
C4	0.0565 (3)	0.6495 (3)	0.49520 (5)	0.0149 (4)
H4	0.0812	0.7999	0.4785	0.018*
C1	0.5354 (4)	0.8550 (4)	0.53973 (6)	0.0208 (4)
H1A	0.6752	0.8380	0.5515	0.025*
H1B	0.5744	1.0283	0.5450	0.025*
C7	0.2139 (3)	0.3542 (3)	0.50634 (5)	0.0159 (4)
H7A	0.3369	0.3067	0.4966	0.019*
H7B	0.0450	0.2111	0.5013	0.019*
C5	0.0986 (4)	0.7091 (4)	0.54597 (5)	0.0188 (4)
H5A	0.1340	0.8814	0.5510	0.023*
H5B	−0.0557	0.5956	0.5624	0.023*
C3	0.2487 (3)	0.5801 (3)	0.47977 (6)	0.0141 (4)
H3	0.2279	0.5406	0.4471	0.017*
C6	0.2509 (4)	0.4253 (4)	0.55649 (6)	0.0204 (4)
H6A	0.0984	0.3095	0.5732	0.024*
H6B	0.3897	0.4068	0.5684	0.024*

	U11	U22	U33	U12	U13	U23
O1	0.0134 (6)	0.0222 (6)	0.0150 (6)	0.0076 (5)	−0.0012 (4)	−0.0004 (5)
N1	0.0176 (7)	0.0155 (8)	0.0128 (7)	0.0074 (6)	−0.0005 (6)	−0.0014 (5)
C2	0.0149 (8)	0.0186 (9)	0.0145 (8)	0.0069 (7)	0.0009 (7)	0.0010 (6)
C4	0.0150 (8)	0.0161 (8)	0.0138 (8)	0.0079 (7)	−0.0002 (6)	0.0006 (7)
C1	0.0176 (9)	0.0215 (9)	0.0164 (9)	0.0045 (8)	−0.0020 (6)	−0.0034 (7)
C7	0.0150 (8)	0.0151 (8)	0.0177 (8)	0.0077 (7)	−0.0012 (6)	−0.0028 (7)
C5	0.0207 (9)	0.0237 (9)	0.0153 (8)	0.0135 (8)	−0.0006 (7)	−0.0042 (7)
C3	0.0135 (8)	0.0158 (8)	0.0124 (8)	0.0068 (7)	−0.0011 (6)	−0.0024 (7)
C6	0.0292 (9)	0.0186 (9)	0.0159 (9)	0.0139 (8)	−0.0003 (8)	0.0013 (7)

O1—H1	0.8400	C1—H1A	0.9900
O1—C4	1.423 (2)	C1—H1B	0.9900
N1—C1	1.475 (2)	C7—H7A	0.9900
N1—C5	1.475 (2)	C7—H7B	0.9900
N1—C6	1.479 (2)	C7—C3	1.530 (2)
C2—H2A	0.9900	C7—C6	1.546 (2)
C2—H2B	0.9900	C5—H5A	0.9900
C2—C1	1.548 (2)	C5—H5B	0.9900
C2—C3	1.536 (2)	C3—H3	1.0000
C4—H4	1.0000	C6—H6A	0.9900
C4—C5	1.552 (2)	C6—H6B	0.9900
C4—C3	1.528 (2)
C4—O1—H1	109.5	C3—C7—H7A	110.1
C1—N1—C6	108.86 (15)	C3—C7—H7B	110.1
C5—N1—C1	108.73 (14)	C3—C7—C6	107.96 (13)
C5—N1—C6	108.72 (14)	C6—C7—H7A	110.1
H2A—C2—H2B	108.4	C6—C7—H7B	110.1
C1—C2—H2A	110.0	N1—C5—C4	112.56 (14)
C1—C2—H2B	110.0	N1—C5—H5A	109.1
C3—C2—H2A	110.0	N1—C5—H5B	109.1
C3—C2—H2B	110.0	C4—C5—H5A	109.1
C3—C2—C1	108.29 (15)	C4—C5—H5B	109.1
O1—C4—H4	109.6	H5A—C5—H5B	107.8
O1—C4—C5	107.46 (13)	C2—C3—H3	109.9
O1—C4—C3	112.96 (14)	C4—C3—C2	108.41 (14)
C5—C4—H4	109.6	C4—C3—C7	109.25 (14)
C3—C4—H4	109.6	C4—C3—H3	109.9
C3—C4—C5	107.45 (13)	C7—C3—C2	109.45 (14)
N1—C1—C2	111.72 (14)	C7—C3—H3	109.9
N1—C1—H1A	109.3	N1—C6—C7	112.19 (14)
N1—C1—H1B	109.3	N1—C6—H6A	109.2
C2—C1—H1A	109.3	N1—C6—H6B	109.2
C2—C1—H1B	109.3	C7—C6—H6A	109.2
H1A—C1—H1B	107.9	C7—C6—H6B	109.2
H7A—C7—H7B	108.4	H6A—C6—H6B	107.9
O1—C4—C5—N1	122.04 (17)	C5—C4—C3—C2	−59.75 (17)
O1—C4—C3—C2	−178.09 (13)	C5—C4—C3—C7	59.46 (17)
O1—C4—C3—C7	−58.88 (17)	C3—C2—C1—N1	−0.9 (2)
C1—N1—C5—C4	59.38 (18)	C3—C4—C5—N1	0.20 (19)
C1—N1—C6—C7	−59.78 (19)	C3—C7—C6—N1	0.4 (2)
C1—C2—C3—C4	60.54 (19)	C6—N1—C1—C2	59.72 (19)
C1—C2—C3—C7	−58.55 (18)	C6—N1—C5—C4	−59.01 (19)
C5—N1—C1—C2	−58.6 (2)	C6—C7—C3—C2	58.56 (18)
C5—N1—C6—C7	58.53 (19)	C6—C7—C3—C4	−60.01 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.84	2.00	2.8366 (19)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.84	2.00	2.8366 (19)	176

Symmetry code: (i) .