2,2',2'',2'''-[Pyridine-2,6-diylbis(methyl-ene-nitrilo)]tetra-ethanol.

In the crystal structure of the title compound C(15)H(27)N(3)O(4), the mol-ecule is located on a twofold axis and the asymmetric unit contains one half-mol-ecule, with one N and one C atom lying on the rotation axis. The pyridine ring is the hydrogen-bond acceptor, while two hydroxyl O atoms act as hydrogen-bond donors in intra-molecular O-H⋯N and intermolecular O-H⋯N and O-H⋯O hydrogen bonds, thereby forming a closed hydrogen-bonded cage.

Related literature

For general background to pyridine, see: Klimesova et al. (1990 ▶); Rabasseda et al. (1999 ▶) . For the synthesis, see: Fang et al. (2010 ▶).

Experimental

Crystal data

C15H27N3O4

M = 313.40

Orthorhombic,

a = 9.145 (6) Å

b = 10.716 (7) Å

c = 8.292 (5) Å

V = 812.6 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.45 × 0.45 × 0.45 mm

Data collection

Bruker SMART APEX diffractometer

4239 measured reflections

1511 independent reflections

1441 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.08

1511 reflections

104 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010919/rk2270sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010919/rk2270Isup2.hkl

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

C15H27N3O4	F(000) = 340
Mr = 313.40	Dx = 1.281 Mg m−3
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 2637 reflections
a = 9.145 (6) Å	θ = 2.5–27.1°
b = 10.716 (7) Å	µ = 0.09 mm−1
c = 8.292 (5) Å	T = 298 K
V = 812.6 (9) Å3	Block, colourless
Z = 2	0.45 × 0.45 × 0.45 mm

Bruker SMART APEX diffractometer	1441 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
graphite	θmax = 25.5°, θmin = 2.5°
φ– and ω–scans	h = −11→8
4239 measured reflections	k = −9→12
1511 independent reflections	l = −10→8

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0466P)2 + 0.1402P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1511 reflections	Δρmax = 0.14 e Å−3
104 parameters	Δρmin = −0.16 e Å−3
1 restraint	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.105 (9)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.0000	1.0000	0.8502 (3)	0.0603 (7)
H1	0.0000	1.0000	0.9624	0.072*
C2	0.0769 (2)	0.91187 (18)	0.7667 (2)	0.0537 (5)
H2	0.1312	0.8520	0.8215	0.064*
C3	0.07333 (19)	0.91260 (16)	0.6004 (2)	0.0453 (4)
C4	0.1444 (2)	0.81022 (17)	0.5072 (2)	0.0564 (5)
H4A	0.2346	0.7873	0.5610	0.068*
H4B	0.0806	0.7379	0.5090	0.068*
C5	0.29756 (19)	0.93047 (18)	0.3315 (3)	0.0590 (5)
H5A	0.3889	0.8861	0.3158	0.071*
H5B	0.3040	0.9755	0.4328	0.071*
C6	0.2762 (2)	1.02106 (18)	0.1970 (2)	0.0567 (5)
H6A	0.3634	1.0719	0.1855	0.068*
H6B	0.2618	0.9757	0.0970	0.068*
C7	0.2098 (2)	0.72780 (17)	0.2461 (3)	0.0617 (5)
H7A	0.2738	0.6747	0.3093	0.074*
H7B	0.2628	0.7520	0.1497	0.074*
C8	0.0801 (3)	0.65392 (18)	0.1972 (3)	0.0671 (5)
H8A	0.1129	0.5729	0.1595	0.081*
H8B	0.0193	0.6403	0.2914	0.081*
N1	0.0000	1.0000	0.5180 (2)	0.0460 (5)
N2	0.17740 (14)	0.84064 (12)	0.34005 (17)	0.0443 (4)
O1	0.15472 (15)	1.09903 (12)	0.22517 (18)	0.0608 (4)
H1A	0.0944	1.0617	0.2802	0.091*
O2	−0.0051 (2)	0.70862 (16)	0.0769 (2)	0.0867 (5)
H2A	−0.0531	0.7659	0.1157	0.130*

	U11	U22	U33	U12	U13	U23
C1	0.0685 (17)	0.0814 (19)	0.0309 (11)	−0.0226 (16)	0.000	0.000
C2	0.0567 (10)	0.0636 (11)	0.0408 (9)	−0.0147 (9)	−0.0090 (8)	0.0123 (8)
C3	0.0449 (9)	0.0501 (9)	0.0410 (8)	−0.0046 (8)	−0.0020 (7)	0.0090 (7)
C4	0.0620 (11)	0.0540 (10)	0.0533 (11)	0.0119 (9)	−0.0016 (9)	0.0147 (8)
C5	0.0383 (9)	0.0654 (11)	0.0734 (12)	0.0017 (8)	−0.0028 (9)	0.0111 (10)
C6	0.0450 (9)	0.0621 (11)	0.0631 (11)	−0.0064 (8)	0.0069 (9)	0.0084 (10)
C7	0.0612 (11)	0.0542 (10)	0.0696 (12)	0.0205 (10)	0.0148 (10)	0.0044 (9)
C8	0.0867 (14)	0.0460 (10)	0.0687 (12)	0.0053 (10)	0.0155 (10)	−0.0064 (9)
N1	0.0536 (11)	0.0513 (11)	0.0333 (9)	0.0073 (10)	0.000	0.000
N2	0.0406 (7)	0.0433 (7)	0.0491 (8)	0.0064 (6)	0.0038 (6)	0.0053 (6)
O1	0.0550 (8)	0.0577 (7)	0.0697 (9)	0.0026 (6)	0.0056 (6)	0.0142 (7)
O2	0.0996 (12)	0.0797 (11)	0.0807 (10)	0.0185 (9)	−0.0140 (10)	−0.0251 (8)

C1—C2i	1.366 (2)	C6—O1	1.410 (2)
C1—C2	1.366 (2)	C6—H6A	0.9700
C1—H1	0.9300	C6—H6B	0.9700
C2—C3	1.380 (3)	C7—N2	1.469 (2)
C2—H2	0.9300	C7—C8	1.482 (3)
C3—N1	1.339 (2)	C7—H7A	0.9700
C3—C4	1.491 (3)	C7—H7B	0.9700
C4—N2	1.455 (2)	C8—O2	1.395 (3)
C4—H4A	0.9700	C8—H8A	0.9700
C4—H4B	0.9700	C8—H8B	0.9700
C5—N2	1.463 (2)	N1—C3i	1.339 (2)
C5—C6	1.491 (3)	O1—H1A	0.8200
C5—H5A	0.9700	O2—H2A	0.8200
C5—H5B	0.9700
C2i—C1—C2	119.1 (2)	C5—C6—H6A	109.3
C2i—C1—H1	120.5	O1—C6—H6B	109.3
C2—C1—H1	120.5	C5—C6—H6B	109.3
C1—C2—C3	119.4 (2)	H6A—C6—H6B	108.0
C1—C2—H2	120.3	N2—C7—C8	115.04 (16)
C3—C2—H2	120.3	N2—C7—H7A	108.5
N1—C3—C2	121.73 (18)	C8—C7—H7A	108.5
N1—C3—C4	117.91 (15)	N2—C7—H7B	108.5
C2—C3—C4	120.25 (18)	C8—C7—H7B	108.5
N2—C4—C3	114.79 (14)	H7A—C7—H7B	107.5
N2—C4—H4A	108.6	O2—C8—C7	114.72 (18)
C3—C4—H4A	108.6	O2—C8—H8A	108.6
N2—C4—H4B	108.6	C7—C8—H8A	108.6
C3—C4—H4B	108.6	O2—C8—H8B	108.6
H4A—C4—H4B	107.5	C7—C8—H8B	108.6
N2—C5—C6	111.48 (16)	H8A—C8—H8B	107.6
N2—C5—H5A	109.3	C3i—N1—C3	118.6 (2)
C6—C5—H5A	109.3	C4—N2—C5	110.45 (16)
N2—C5—H5B	109.3	C4—N2—C7	111.27 (14)
C6—C5—H5B	109.3	C5—N2—C7	111.38 (15)
H5A—C5—H5B	108.0	C6—O1—H1A	109.5
O1—C6—C5	111.42 (17)	C8—O2—H2A	109.5
O1—C6—H6A	109.3
C2i—C1—C2—C3	−1.04 (13)	C4—C3—N1—C3i	175.19 (18)
C1—C2—C3—N1	2.2 (3)	C3—C4—N2—C5	70.9 (2)
C1—C2—C3—C4	−174.02 (14)	C3—C4—N2—C7	−164.87 (16)
N1—C3—C4—N2	23.7 (2)	C6—C5—N2—C4	−143.71 (17)
C2—C3—C4—N2	−160.01 (17)	C6—C5—N2—C7	92.11 (19)
N2—C5—C6—O1	66.6 (2)	C8—C7—N2—C4	77.8 (2)
N2—C7—C8—O2	71.9 (2)	C8—C7—N2—C5	−158.52 (17)
C2—C3—N1—C3i	−1.09 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1i	0.82	1.94	2.762 (2)	175
O1—H1A···N2i	0.82	2.74	3.248 (2)	122
O1—H1A···N2	0.82	2.54	2.935 (2)	111
O1—H1A···N1	0.82	2.25	3.004 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1i	0.82	1.94	2.762 (2)	175
O1—H1A⋯N2i	0.82	2.74	3.248 (2)	122
O1—H1A⋯N2	0.82	2.54	2.935 (2)	111
O1—H1A⋯N1	0.82	2.25	3.004 (2)	153

Symmetry code: (i) .