2,2'-[(2S*,6R*)-Piperidine-2,6-di-yl]-di-pro-pan-2-ol.

In the title compound, C(11)H(23)NO(2), the piperidine ring has a chair conformation. The two hy-droxy H atoms are disordered over two positions with fixed occupancy ratios of 0.57:0.43 and 0.63:0.37. In the mol-ecule, there are two short N-H⋯O inter-actions. In the crystal, four symmetry-related mol-ecules are linked by O-H⋯O hydrogen bonds to form a cage-like arrangement, centered about the point of inter-section of three twofold axes. These cages stack along the [100] direction.

Related literature

For literature on ligands of the pincer-type family, see: van Koten (1989 ▶); Albrecht & van Koten (2001 ▶). For metal complexes of such pincer ligands, see: Hofmeier & Schubert (2004 ▶); Li et al. (2007 ▶). For the synthesis of the starting material 2,2′-(pyridine-2,6-di­yl)dipropan-2-ol, see: Klein et al. (2009 ▶). For an example of the transformation of bis-benzylic alcohols of 2,6-disubstituted pyridines, see: Klein et al. (2009 ▶). For the crystal structure of cis-(piperidine-2,6-di­yl)di­me­than­ol, see: Hartung et al. (2007 ▶).

Experimental

Crystal data

C11H23NO2

M = 201.30

Orthorhombic,

a = 12.0713 (9) Å

b = 23.4762 (10) Å

c = 34.496 (2) Å

V = 9775.8 (10) Å3

Z = 32

Mo Kα radiation

μ = 0.07 mm−1

T = 173 K

0.45 × 0.45 × 0.40 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009 ▶) T min = 0.911, T max = 1.000

32226 measured reflections

2319 independent reflections

1499 reflections with I > 2σ(I)

R int = 0.135

Refinement

R[F 2 > 2σ(F 2)] = 0.086

wR(F 2) = 0.146

S = 1.16

2319 reflections

135 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: X-AREA (Stoe & Cie, 2009 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005879/pk2389sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005879/pk2389Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005879/pk2389Isup3.cml

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

C11H23NO2	Dx = 1.094 Mg m−3
Mr = 201.30	Melting point: 345.3 K
Orthorhombic, Fddd	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -F 2uv 2vw	Cell parameters from 13139 reflections
a = 12.0713 (9) Å	θ = 2.0–24.3°
b = 23.4762 (10) Å	µ = 0.07 mm−1
c = 34.496 (2) Å	T = 173 K
V = 9775.8 (10) Å3	Rod, colourless
Z = 32	0.45 × 0.45 × 0.40 mm
F(000) = 3584

Stoe IPDS 2 diffractometer	2319 independent reflections
Radiation source: fine-focus sealed tube	1499 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.135
φ & ω scans	θmax = 25.7°, θmin = 2.0°
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009)	h = −14→14
Tmin = 0.911, Tmax = 1.000	k = −28→28
32226 measured reflections	l = −42→41

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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0468P)2 + 7.437P] where P = (Fo2 + 2Fc2)/3
2319 reflections	(Δ/σ)max < 0.001
135 parameters	Δρmax = 0.16 e Å−3
4 restraints	Δρmin = −0.15 e Å−3

Experimental. Spectroscopic data for 2,2'-((2S*,6R*)-piperidine-2,6-diyl)dipropan-2-ol (2):1H NMR (CDCl3, 298 K, p.p.m.) δ 2.88 (bs, 2 H, OH), 2.47 (d, 3J(2, 3 b) and 3J(6, 5 b) = 11.4 Hz, 2 H, C—H(2, 6)), 1.97 (dquint, 3J(4 b, 4a) = 13.3 Hz, 3J(4 b, 3 b) = 3 J(4 b, 5 b) = 3.3 Hz, 3J(4 b, 3a) = 3J(4 b, 5a) = 3.3 Hz, 1 H, C—H(4 b)), 1.74 (dd, 3J(3a, 3 b) = 12.8 Hz and 3J(5a, 5 b) = 12.8 Hz, 3J(3a, 4 b) = 3.0 Hz and 3J(5a, 4 b) = 3.0 Hz, 2 H, C—H(3a, 5a)), 1.45 (qt, 3J(4a, 4 b) = 13.0 Hz, 3J(4a, 3 b) = 13.0 Hz and 3J(4a, 5 b) = 13.0 Hz, 3 J(4a, 3a) = 3.7 Hz and 3J(4a, 5a) = 3.7 Hz, 1 H, C—H(4a)), 1.25 (s, 6 H, CH3), 1.16 (s, 6 H, CH3), 1.06 (qd, 3J(3 b, 2) = 12.3 Hz and 3J(5 b, 6) = 12.3 Hz, 3J(3 b, 3a) = 12.3 Hz and 3J(5 b, 5a) = 12.3 Hz, 3J(3 b, 4a) = 12.3 Hz and 3J(5 b, 4a) = 12.3 Hz, 3J(3 b, 4 b) = 3.3 Hz and 3J(5 b, 4 b) = 3.3 Hz, 2 H, CH2(3 b, 5 b));13C NMR (CDCl3, 298 K, p.p.m.) δ 71.67 (C(2, 2')), 65.45 (C(2, 6)), 27.45 (CH3), 26.91 (C(3, 5)), 24.69 (C(4)), 24.36 (CH3).IR (KBr, cm-1): 3377 b s, 2982 s, 2944 s, 2855m, 2782m, 2694w, 2586w, 1456m, 1442m, 1380 s, 1130 s, 931 s, 822 s, 537w.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. The NH H-atom was located in a difference Fourier map and was freely refined. The OH H atoms are disordered over two positions with fixed occupancies of 0.57/0.43 and 0.63/0.37. They were located in a difference Fourier map and were initially freely refined, including their occupancies, before being refined with distance restraints of 0.84 (2) Å. In the final cycles of refinement they were refined with fixed occupancies of 0.57/0.43 and 0.63/0.37, and allowed to ride on the parent O atom with Uiso(H) = 1.5Ueq(O). The C-bound H-atoms were included in calculated positions and treated as riding atoms: C—H = 0.98, 0.99 and 1.00 Å for CH3, CH2 and CH H-atoms, respectively, with Uiso(H) = k × Ueq(parent C-atom), where k = 1.5 for CH3 H-atoms and k = 1.2 for all other H-atoms.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1'	0.52422 (16)	0.09518 (8)	0.04534 (5)	0.0474 (7)
O1''	0.51927 (19)	0.22777 (8)	0.14029 (6)	0.0602 (8)
N1	0.41660 (19)	0.19356 (10)	0.07083 (6)	0.0344 (7)
C1'	0.4778 (3)	0.15489 (12)	−0.00855 (8)	0.0490 (10)
C1''	0.4860 (3)	0.30648 (12)	0.09761 (9)	0.0551 (11)
C2	0.3546 (2)	0.22205 (11)	0.10141 (8)	0.0426 (10)
C2'	0.4316 (2)	0.11656 (11)	0.02325 (8)	0.0410 (10)
C2''	0.4314 (3)	0.26220 (11)	0.12374 (8)	0.0496 (10)
C3	0.2533 (3)	0.25074 (14)	0.08304 (10)	0.0602 (13)
C3'	0.3740 (3)	0.06505 (14)	0.00542 (10)	0.0730 (14)
C3''	0.3697 (4)	0.29130 (15)	0.15692 (10)	0.0900 (16)
C4	0.1844 (2)	0.20695 (15)	0.06117 (11)	0.0712 (13)
C5	0.2544 (2)	0.17559 (14)	0.03176 (10)	0.0554 (11)
C6	0.3549 (2)	0.14843 (11)	0.05111 (8)	0.0391 (9)
H1	0.472 (2)	0.1777 (11)	0.0809 (7)	0.035 (8)*
H1A	0.51390	0.07430	0.06420	0.0710*	0.570
H1C	0.51740	0.20950	0.16040	0.0900*	0.630
H1L	0.51510	0.18770	0.00320	0.0740*
H1M	0.41710	0.16820	−0.02510	0.0740*
H1N	0.53100	0.13340	−0.02420	0.0740*
H1O	0.53320	0.28730	0.07860	0.0830*
H1P	0.53110	0.33230	0.11340	0.0830*
H1Q	0.42860	0.32830	0.08410	0.0830*
H2	0.32750	0.19230	0.11990	0.0510*
H3A	0.20760	0.26860	0.10350	0.0720*
H3B	0.27790	0.28100	0.06500	0.0720*
H3C	0.42710	0.04350	−0.01030	0.1090*
H3D	0.31270	0.07790	−0.01100	0.1090*
H3E	0.34510	0.04060	0.02610	0.1090*
H3F	0.32950	0.26260	0.17200	0.1350*
H3G	0.31710	0.31900	0.14630	0.1350*
H3H	0.42300	0.31090	0.17370	0.1350*
H4A	0.15250	0.17930	0.07980	0.0850*
H4B	0.12240	0.22640	0.04780	0.0850*
H5A	0.20940	0.14570	0.01910	0.0670*
H5B	0.27950	0.20250	0.01150	0.0670*
H6	0.32790	0.12090	0.07110	0.0470*
H1B	0.57870	0.11630	0.04260	0.0710*	0.430
H1D	0.57710	0.24160	0.13160	0.0900*	0.370

	U11	U22	U33	U12	U13	U23
O1'	0.0614 (13)	0.0440 (11)	0.0367 (12)	0.0143 (10)	−0.0002 (10)	0.0061 (9)
O1''	0.0968 (18)	0.0448 (12)	0.0391 (12)	0.0016 (12)	−0.0205 (12)	0.0086 (10)
N1	0.0292 (12)	0.0401 (13)	0.0340 (13)	0.0063 (11)	−0.0009 (11)	0.0029 (11)
C1'	0.0569 (19)	0.0521 (18)	0.0381 (17)	0.0011 (15)	0.0021 (15)	0.0106 (14)
C1''	0.073 (2)	0.0422 (17)	0.050 (2)	−0.0020 (16)	−0.0034 (17)	0.0073 (15)
C2	0.0459 (17)	0.0385 (15)	0.0435 (18)	0.0099 (14)	0.0160 (14)	0.0092 (14)
C2'	0.0513 (18)	0.0373 (16)	0.0345 (16)	−0.0044 (14)	−0.0085 (14)	0.0051 (13)
C2''	0.076 (2)	0.0388 (15)	0.0340 (17)	0.0091 (16)	0.0109 (16)	0.0048 (14)
C3	0.0441 (18)	0.0564 (19)	0.080 (3)	0.0191 (15)	0.0206 (17)	0.0162 (19)
C3'	0.112 (3)	0.057 (2)	0.050 (2)	−0.026 (2)	−0.014 (2)	−0.0008 (17)
C3''	0.158 (4)	0.061 (2)	0.051 (2)	0.023 (2)	0.038 (3)	−0.0051 (19)
C4	0.0315 (17)	0.075 (2)	0.107 (3)	0.0104 (17)	−0.0006 (19)	0.037 (2)
C5	0.0342 (17)	0.066 (2)	0.066 (2)	−0.0054 (15)	−0.0126 (16)	0.0203 (18)
C6	0.0359 (15)	0.0429 (16)	0.0384 (17)	−0.0065 (13)	−0.0060 (13)	0.0128 (13)

O1'—C2'	1.443 (3)	C1'—H1M	0.9800
O1''—C2''	1.451 (4)	C1'—H1N	0.9800
O1'—H1B	0.8300	C1''—H1O	0.9800
O1'—H1A	0.8200	C1''—H1P	0.9800
O1''—H1C	0.8200	C1''—H1Q	0.9800
O1''—H1D	0.8300	C2—H2	1.0000
N1—C6	1.463 (3)	C3—H3A	0.9900
N1—C2	1.456 (3)	C3—H3B	0.9900
N1—H1	0.84 (2)	C3'—H3C	0.9800
C1'—C2'	1.525 (4)	C3'—H3D	0.9800
C1''—C2''	1.526 (4)	C3'—H3E	0.9800
C2—C2''	1.530 (4)	C3''—H3F	0.9800
C2—C3	1.533 (4)	C3''—H3G	0.9800
C2'—C3'	1.525 (4)	C3''—H3H	0.9800
C2'—C6	1.530 (4)	C4—H4A	0.9900
C2''—C3''	1.527 (5)	C4—H4B	0.9900
C3—C4	1.522 (5)	C5—H5A	0.9900
C4—C5	1.512 (5)	C5—H5B	0.9900
C5—C6	1.524 (4)	C6—H6	1.0000
C1'—H1L	0.9800
C2'—O1'—H1A	120.00	H1O—C1''—H1P	109.00
C2'—O1'—H1B	110.00	H1O—C1''—H1Q	109.00
C2''—O1''—H1C	127.00	H1P—C1''—H1Q	110.00
C2''—O1''—H1D	105.00	N1—C2—H2	108.00
C2—N1—C6	114.1 (2)	C2''—C2—H2	108.00
C6—N1—H1	106.1 (18)	C3—C2—H2	108.00
C2—N1—H1	108.2 (17)	C2—C3—H3A	110.00
N1—C2—C3	108.2 (2)	C2—C3—H3B	110.00
N1—C2—C2''	109.7 (2)	C4—C3—H3A	110.00
C2''—C2—C3	114.9 (2)	C4—C3—H3B	110.00
O1'—C2'—C6	107.9 (2)	H3A—C3—H3B	108.00
O1'—C2'—C1'	107.6 (2)	C2'—C3'—H3C	110.00
O1'—C2'—C3'	106.9 (2)	C2'—C3'—H3D	109.00
C1'—C2'—C6	112.6 (2)	C2'—C3'—H3E	109.00
C3'—C2'—C6	111.4 (2)	H3C—C3'—H3D	109.00
C1'—C2'—C3'	110.2 (2)	H3C—C3'—H3E	109.00
C1''—C2''—C2	112.6 (2)	H3D—C3'—H3E	109.00
C1''—C2''—C3''	110.4 (2)	C2''—C3''—H3F	109.00
O1''—C2''—C1''	107.2 (3)	C2''—C3''—H3G	109.00
O1''—C2''—C2	107.3 (2)	C2''—C3''—H3H	109.00
O1''—C2''—C3''	108.1 (2)	H3F—C3''—H3G	110.00
C2—C2''—C3''	110.9 (3)	H3F—C3''—H3H	110.00
C2—C3—C4	110.1 (3)	H3G—C3''—H3H	110.00
C3—C4—C5	110.9 (2)	C3—C4—H4A	109.00
C4—C5—C6	110.8 (3)	C3—C4—H4B	109.00
C2'—C6—C5	114.3 (2)	C5—C4—H4A	109.00
N1—C6—C2'	109.8 (2)	C5—C4—H4B	110.00
N1—C6—C5	107.8 (2)	H4A—C4—H4B	108.00
C2'—C1'—H1L	110.00	C4—C5—H5A	110.00
C2'—C1'—H1M	110.00	C4—C5—H5B	110.00
C2'—C1'—H1N	109.00	C6—C5—H5A	109.00
H1L—C1'—H1M	110.00	C6—C5—H5B	109.00
H1L—C1'—H1N	109.00	H5A—C5—H5B	108.00
H1M—C1'—H1N	109.00	N1—C6—H6	108.00
C2''—C1''—H1O	110.00	C2'—C6—H6	108.00
C2''—C1''—H1P	109.00	C5—C6—H6	108.00
C2''—C1''—H1Q	109.00
C6—N1—C2—C2''	172.0 (2)	C2''—C2—C3—C4	179.1 (3)
C6—N1—C2—C3	−62.0 (3)	O1'—C2'—C6—N1	56.7 (3)
C2—N1—C6—C2'	−173.0 (2)	O1'—C2'—C6—C5	177.9 (2)
C2—N1—C6—C5	62.0 (3)	C1'—C2'—C6—N1	−61.9 (3)
N1—C2—C2''—O1''	−60.2 (3)	C1'—C2'—C6—C5	59.4 (3)
N1—C2—C2''—C1''	57.6 (3)	C3'—C2'—C6—N1	173.7 (2)
N1—C2—C2''—C3''	−178.1 (2)	C3'—C2'—C6—C5	−65.0 (3)
C3—C2—C2''—O1''	177.7 (2)	C2—C3—C4—C5	−54.9 (4)
C3—C2—C2''—C1''	−64.5 (3)	C3—C4—C5—C6	55.4 (4)
C3—C2—C2''—C3''	59.8 (3)	C4—C5—C6—N1	−56.7 (3)
N1—C2—C3—C4	56.2 (3)	C4—C5—C6—C2'	−179.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1′	0.84 (3)	2.38 (3)	2.792 (3)	111 (2)
N1—H1···O1′′	0.84 (3)	2.43 (3)	2.814 (3)	109 (2)
O1′—H1A···O1′′i	0.82	1.99	2.805 (3)	169
O1′—H1B···O1′ii	0.83	1.99	2.807 (4)	167
O1′′—H1C···O1′i	0.82	2.00	2.805 (3)	171
O1′′—H1D···O1′′iii	0.83	2.03	2.762 (5)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1′	0.84 (3)	2.38 (3)	2.792 (3)	111 (2)
N1—H1⋯O1′′	0.84 (3)	2.43 (3)	2.814 (3)	109 (2)
O1′—H1A⋯O1′′i	0.82	1.99	2.805 (3)	169
O1′—H1B⋯O1′ii	0.83	1.99	2.807 (4)	167
O1′′—H1C⋯O1′i	0.82	2.00	2.805 (3)	171
O1′′—H1D⋯O1′′iii	0.83	2.03	2.762 (5)	148

Symmetry codes: (i) ; (ii) ; (iii) .