2,2'-[Ethyl-enebis(azanediyl-methyl-ene)]diphenol.

In the title compound, C(16)H(20)N(2)O(4), the mol-ecule features a zigzag -CH(2)-NH-CH(2)-CH(2)-NH-CH(2)- chain whose ends are connected to the hydroxy-phenyl rings. The mol-ecules lies about a center of inversion. The imino group is a hydrogen-bond donor for the hydr-oxy group, which is a hydrogen-bond donor for the imino group of an adjacent mol-ecule. This latter inter-molecular hydrogen bonding leads to a layer structure.

Related literature

The title compound was doubly-deprotonated, forming several tetra­dentate chelated metal complexes. For their crystal structures, see: Atwood et al. (1995 ▶, 1996 ▶); Borer et al. (1983 ▶); Bottcher et al. (1994 ▶); García-Zarracino et al. (2002 ▶); Henrick et al. (1984 ▶); Viswanathan et al. (1998 ▶); Xie et al. (2006 ▶); Yang et al. (2007 ▶).

Experimental

Crystal data

C16H20N2O2

M = 272.34

Monoclinic,

a = 15.263 (2) Å

b = 4.860 (1) Å

c = 9.770 (1) Å

β = 96.318 (3)°

V = 720.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.31 × 0.27 × 0.25 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.975, T max = 0.979

6726 measured reflections

1635 independent reflections

912 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.176

S = 1.09

1635 reflections

99 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.19 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048831/xu2679sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048831/xu2679Isup2.hkl

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

C16H20N2O2	F(000) = 292
Mr = 272.34	Dx = 1.256 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3415 reflections
a = 15.263 (2) Å	θ = 4.0–27.4°
b = 4.860 (1) Å	µ = 0.08 mm−1
c = 9.770 (1) Å	T = 293 K
β = 96.318 (3)°	Prism, colorless
V = 720.3 (2) Å3	0.31 × 0.27 × 0.25 mm
Z = 2

Rigaku R-AXIS RAPID IP diffractometer	1635 independent reflections
Radiation source: fine-focus sealed tube	912 reflections with I > 2σ(I)
graphite	Rint = 0.055
ω scan	θmax = 27.4°, θmin = 4.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −19→19
Tmin = 0.975, Tmax = 0.979	k = −6→6
6726 measured reflections	l = −12→11

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0749P)2 + 0.1302P] where P = (Fo2 + 2Fc2)/3
1635 reflections	(Δ/σ)max = 0.001
99 parameters	Δρmax = 0.21 e Å−3
2 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.34270 (10)	0.3118 (4)	0.13029 (16)	0.0555 (5)
N1	0.38397 (11)	0.4899 (4)	0.41165 (18)	0.0451 (5)
C1	0.25836 (14)	0.3821 (5)	0.1507 (2)	0.0439 (6)
C2	0.18572 (15)	0.2708 (5)	0.0744 (2)	0.0552 (6)
H2A	0.1932	0.1404	0.0070	0.066*
C3	0.10190 (15)	0.3510 (6)	0.0972 (3)	0.0622 (7)
H3	0.0532	0.2732	0.0460	0.075*
C4	0.09036 (16)	0.5466 (6)	0.1958 (3)	0.0624 (7)
H4	0.0340	0.6040	0.2103	0.075*
C5	0.16325 (16)	0.6564 (5)	0.2727 (2)	0.0564 (7)
H5	0.1552	0.7871	0.3397	0.068*
C6	0.24808 (13)	0.5773 (5)	0.2530 (2)	0.0443 (6)
C7	0.32748 (15)	0.6983 (5)	0.3364 (2)	0.0524 (6)
H7A	0.3621	0.7987	0.2754	0.063*
H7B	0.3079	0.8285	0.4019	0.063*
C8	0.46843 (13)	0.6100 (5)	0.4701 (2)	0.0497 (6)
H8A	0.4579	0.7403	0.5418	0.060*
H8B	0.4947	0.7091	0.3988	0.060*
H1O	0.3458 (18)	0.209 (5)	0.0600 (19)	0.081 (10)*
H1N	0.3943 (15)	0.370 (4)	0.3504 (19)	0.060 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0458 (10)	0.0730 (13)	0.0477 (10)	0.0062 (8)	0.0060 (7)	−0.0106 (8)
N1	0.0441 (10)	0.0469 (12)	0.0432 (10)	−0.0043 (8)	0.0005 (8)	−0.0013 (9)
C1	0.0434 (12)	0.0475 (13)	0.0409 (11)	0.0033 (10)	0.0055 (9)	0.0053 (10)
C2	0.0546 (14)	0.0616 (16)	0.0482 (13)	−0.0008 (11)	−0.0005 (11)	−0.0064 (12)
C3	0.0457 (14)	0.0746 (19)	0.0642 (16)	−0.0037 (12)	−0.0036 (12)	0.0023 (14)
C4	0.0465 (13)	0.0746 (19)	0.0660 (16)	0.0126 (13)	0.0065 (12)	0.0082 (14)
C5	0.0565 (14)	0.0592 (16)	0.0536 (14)	0.0127 (12)	0.0074 (11)	0.0000 (11)
C6	0.0489 (13)	0.0424 (13)	0.0418 (11)	0.0012 (9)	0.0050 (10)	0.0039 (9)
C7	0.0570 (14)	0.0458 (14)	0.0532 (13)	0.0055 (11)	0.0014 (11)	0.0000 (11)
C8	0.0480 (13)	0.0493 (15)	0.0510 (13)	−0.0079 (10)	0.0009 (10)	−0.0009 (11)

O1—C1	1.367 (2)	C4—C5	1.380 (4)
O1—H1O	0.86 (1)	C4—H4	0.9300
N1—C8	1.472 (3)	C5—C6	1.384 (3)
N1—C7	1.473 (3)	C5—H5	0.9300
N1—H1N	0.86 (1)	C6—C7	1.504 (3)
C1—C2	1.377 (3)	C7—H7A	0.9700
C1—C6	1.399 (3)	C7—H7B	0.9700
C2—C3	1.379 (3)	C8—C8i	1.513 (4)
C2—H2A	0.9300	C8—H8A	0.9700
C3—C4	1.379 (4)	C8—H8B	0.9700
C3—H3	0.9300
C1—O1—H1O	113.5 (19)	C4—C5—H5	119.1
C8—N1—C7	111.12 (17)	C6—C5—H5	119.1
C8—N1—H1N	108.6 (16)	C5—C6—C1	117.9 (2)
C7—N1—H1N	105.1 (16)	C5—C6—C7	121.7 (2)
O1—C1—C2	122.6 (2)	C1—C6—C7	120.34 (19)
O1—C1—C6	117.04 (19)	N1—C7—C6	113.21 (18)
C2—C1—C6	120.4 (2)	N1—C7—H7A	108.9
C1—C2—C3	120.5 (2)	C6—C7—H7A	108.9
C1—C2—H2A	119.7	N1—C7—H7B	108.9
C3—C2—H2A	119.7	C6—C7—H7B	108.9
C2—C3—C4	120.0 (2)	H7A—C7—H7B	107.8
C2—C3—H3	120.0	N1—C8—C8i	111.3 (2)
C4—C3—H3	120.0	N1—C8—H8A	109.4
C3—C4—C5	119.4 (2)	C8i—C8—H8A	109.4
C3—C4—H4	120.3	N1—C8—H8B	109.4
C5—C4—H4	120.3	C8i—C8—H8B	109.4
C4—C5—C6	121.8 (2)	H8A—C8—H8B	108.0
O1—C1—C2—C3	−179.0 (2)	C2—C1—C6—C5	−1.0 (3)
C6—C1—C2—C3	0.4 (4)	O1—C1—C6—C7	−0.7 (3)
C1—C2—C3—C4	0.8 (4)	C2—C1—C6—C7	179.9 (2)
C2—C3—C4—C5	−1.2 (4)	C8—N1—C7—C6	169.35 (18)
C3—C4—C5—C6	0.6 (4)	C5—C6—C7—N1	122.4 (2)
C4—C5—C6—C1	0.6 (4)	C1—C6—C7—N1	−58.5 (3)
C4—C5—C6—C7	179.7 (2)	C7—N1—C8—C8i	−171.9 (2)
O1—C1—C6—C5	178.39 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1ii	0.86 (1)	1.89 (1)	2.721 (2)	165 (3)
N1—H1n···O1	0.86 (1)	2.23 (2)	2.884 (2)	133 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1i	0.86 (1)	1.89 (1)	2.721 (2)	165 (3)
N1—H1n⋯O1	0.86 (1)	2.23 (2)	2.884 (2)	133 (2)

Symmetry code: (i) .