6,6'-Dihydr-oxy-2,2'-[(pentane-1,5-diyl-dioxy)bis-(nitrilo-methyl-idyne)]diphenol.

The mol-ecule of the title compound, C(19)H(22)N(2)O(6), assumes a W-shaped configuration with the dihedral angle between the two halves of the mol-ecule being 82.48 (5)°. There is one half-mol-ecule in the asymmetric unit with a crystallographic twofold rotation axis passing through the central C atom of the five methylene groups in the [-CH=N-O-(CH(2))(5)-O-N=CH-] bridge. The dihedral angle formed by the two benzene rings in each mol-ecule of the title compound is 84.18 (4)°. There are strong intra-molecular O-H⋯N and O-H⋯O hydrogen bonds and weak inter-molecular π-π stacking inter-actions between neighbouring benzene rings, and the inter-molecular plane-to-plane distances are 3.488 (2) and 3.841 (3) Å along the b and c axes, respectively. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link each mol-ecule to two others, forming an infinite three-dimensional supra-molecular structure.

Related literature

For related literature, see: Akine et al. (2001 ▶, 2005 ▶, 2006 ▶); Atwood (1997 ▶); Dong & Feng (2006 ▶); Dong, Zhao et al. (2008 ▶); Dong, He et al. (2008 ▶); Duan et al. (2007 ▶); Venkataramanan et al. (2005 ▶); Yu et al. (2008 ▶).

Experimental

Crystal data

C19H22N2O6

M = 374.39

Monoclinic,

a = 28.439 (3) Å

b = 4.6997 (6) Å

c = 14.0843 (17) Å

β = 100.354 (2)°

V = 1851.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.46 × 0.27 × 0.25 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.955, T max = 0.975

4246 measured reflections

1621 independent reflections

837 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.135

S = 1.00

1621 reflections

123 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SMART; data reduction: SAINT (Siemens, 1996 ▶); 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 global, I. DOI: 10.1107/S1600536808023064/hg2427sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023064/hg2427Isup2.hkl

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

C19H22N2O6	F000 = 792
Mr = 374.39	Dx = 1.343 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 875 reflections
a = 28.439 (3) Å	θ = 2.9–22.4º
b = 4.6997 (6) Å	µ = 0.10 mm−1
c = 14.0843 (17) Å	T = 298 (2) K
β = 100.354 (2)º	Needle-like, pale-brown
V = 1851.8 (4) Å3	0.46 × 0.27 × 0.25 mm
Z = 4

Siemens SMART 1000 CCD area-detector diffractometer	1621 independent reflections
Radiation source: fine-focus sealed tube	837 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.062
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −33→30
Tmin = 0.955, Tmax = 0.975	k = −5→5
4246 measured reflections	l = −16→16

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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0407P)2 + 1.5785P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1621 reflections	Δρmax = 0.24 e Å−3
123 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	Occ. (<1)
N1	0.40208 (8)	−0.0702 (5)	0.51037 (15)	0.0479 (7)
O1	0.41975 (7)	−0.2344 (4)	0.59236 (12)	0.0542 (6)
O2	0.39611 (7)	0.1384 (5)	0.33535 (13)	0.0637 (7)
H2	0.4076	0.0385	0.3815	0.095*
O3	0.34987 (8)	0.4908 (5)	0.19941 (14)	0.0782 (8)
H3	0.3730	0.3870	0.1991	0.117*
C1	0.46067 (10)	−0.3889 (7)	0.57460 (19)	0.0535 (9)
H1A	0.4849	−0.2576	0.5610	0.064*
H1B	0.4518	−0.5126	0.5192	0.064*
C2	0.47987 (11)	−0.5624 (7)	0.66243 (18)	0.0543 (9)
H2A	0.5048	−0.6868	0.6478	0.065*
H2B	0.4544	−0.6814	0.6780	0.065*
C3	0.5000	−0.3833 (9)	0.7500	0.0500 (11)
H3A	0.4749	−0.2617	0.7657	0.060*	0.50
H3B	0.5251	−0.2617	0.7343	0.060*	0.50
C4	0.36573 (10)	0.0763 (7)	0.52087 (19)	0.0470 (8)
H4	0.3540	0.0644	0.5783	0.056*
C5	0.34239 (9)	0.2611 (6)	0.44479 (18)	0.0418 (7)
C6	0.35833 (10)	0.2865 (6)	0.35701 (19)	0.0439 (7)
C7	0.33496 (11)	0.4666 (7)	0.28589 (19)	0.0509 (8)
C8	0.29684 (11)	0.6252 (7)	0.3023 (2)	0.0573 (9)
H8	0.2819	0.7498	0.2550	0.069*
C9	0.28046 (11)	0.6018 (7)	0.3883 (2)	0.0590 (9)
H9	0.2542	0.7075	0.3985	0.071*
C10	0.30300 (10)	0.4222 (7)	0.4586 (2)	0.0538 (9)
H10	0.2918	0.4075	0.5165	0.065*

	U11	U22	U33	U12	U13	U23
N1	0.0471 (15)	0.0517 (18)	0.0431 (13)	0.0017 (13)	0.0029 (11)	0.0029 (12)
O1	0.0510 (13)	0.0670 (16)	0.0443 (11)	0.0114 (12)	0.0076 (9)	0.0072 (10)
O2	0.0557 (14)	0.0800 (17)	0.0593 (13)	0.0191 (13)	0.0211 (10)	0.0113 (11)
O3	0.0804 (16)	0.099 (2)	0.0575 (13)	0.0188 (15)	0.0195 (12)	0.0206 (13)
C1	0.0520 (19)	0.056 (2)	0.0516 (17)	0.0052 (17)	0.0074 (15)	−0.0072 (15)
C2	0.058 (2)	0.049 (2)	0.0529 (17)	0.0074 (17)	0.0018 (15)	−0.0022 (15)
C3	0.044 (2)	0.049 (3)	0.055 (2)	0.000	0.0043 (19)	0.000
C4	0.0450 (18)	0.056 (2)	0.0408 (15)	−0.0017 (16)	0.0093 (13)	−0.0038 (15)
C5	0.0342 (16)	0.045 (2)	0.0447 (15)	−0.0038 (15)	0.0033 (13)	−0.0061 (13)
C6	0.0365 (16)	0.046 (2)	0.0498 (16)	−0.0021 (15)	0.0093 (13)	−0.0063 (14)
C7	0.053 (2)	0.055 (2)	0.0440 (16)	−0.0018 (17)	0.0059 (14)	0.0002 (15)
C8	0.054 (2)	0.055 (2)	0.0579 (19)	0.0044 (18)	−0.0037 (16)	0.0007 (16)
C9	0.0465 (19)	0.063 (2)	0.066 (2)	0.0112 (17)	0.0040 (16)	−0.0084 (18)
C10	0.0471 (19)	0.062 (2)	0.0521 (17)	0.0012 (17)	0.0099 (14)	−0.0109 (16)

N1—C4	1.273 (3)	C3—H3A	0.9700
N1—O1	1.405 (3)	C3—H3B	0.9700
O1—C1	1.431 (3)	C4—C5	1.444 (4)
O2—C6	1.360 (3)	C4—H4	0.9300
O2—H2	0.8200	C5—C10	1.394 (4)
O3—C7	1.364 (3)	C5—C6	1.396 (3)
O3—H3	0.8200	C6—C7	1.386 (4)
C1—C2	1.500 (4)	C7—C8	1.369 (4)
C1—H1A	0.9700	C8—C9	1.378 (4)
C1—H1B	0.9700	C8—H8	0.9300
C2—C3	1.518 (4)	C9—C10	1.370 (4)
C2—H2A	0.9700	C9—H9	0.9300
C2—H2B	0.9700	C10—H10	0.9300
C3—C2i	1.518 (4)
C4—N1—O1	112.3 (2)	N1—C4—C5	120.9 (3)
N1—O1—C1	108.47 (19)	N1—C4—H4	119.5
C6—O2—H2	109.5	C5—C4—H4	119.5
C7—O3—H3	109.5	C10—C5—C6	118.3 (3)
O1—C1—C2	108.6 (2)	C10—C5—C4	119.8 (3)
O1—C1—H1A	110.0	C6—C5—C4	122.0 (3)
C2—C1—H1A	110.0	O2—C6—C7	116.5 (3)
O1—C1—H1B	110.0	O2—C6—C5	123.4 (3)
C2—C1—H1B	110.0	C7—C6—C5	120.2 (3)
H1A—C1—H1B	108.4	O3—C7—C8	119.2 (3)
C1—C2—C3	113.4 (3)	O3—C7—C6	120.7 (3)
C1—C2—H2A	108.9	C8—C7—C6	120.1 (3)
C3—C2—H2A	108.9	C7—C8—C9	120.5 (3)
C1—C2—H2B	108.9	C7—C8—H8	119.8
C3—C2—H2B	108.9	C9—C8—H8	119.8
H2A—C2—H2B	107.7	C10—C9—C8	119.8 (3)
C2—C3—C2i	112.6 (4)	C10—C9—H9	120.1
C2—C3—H3A	109.1	C8—C9—H9	120.1
C2i—C3—H3A	109.1	C9—C10—C5	121.2 (3)
C2—C3—H3B	109.1	C9—C10—H10	119.4
C2i—C3—H3B	109.1	C5—C10—H10	119.4
H3A—C3—H3B	107.8
C4—N1—O1—C1	−179.4 (2)	O2—C6—C7—O3	−0.2 (4)
N1—O1—C1—C2	179.5 (2)	C5—C6—C7—O3	−179.2 (3)
O1—C1—C2—C3	−66.3 (3)	O2—C6—C7—C8	−179.4 (3)
C1—C2—C3—C2i	−178.9 (3)	C5—C6—C7—C8	1.5 (4)
O1—N1—C4—C5	179.6 (2)	O3—C7—C8—C9	178.9 (3)
N1—C4—C5—C10	−179.2 (3)	C6—C7—C8—C9	−1.9 (5)
N1—C4—C5—C6	0.2 (4)	C7—C8—C9—C10	1.2 (5)
C10—C5—C6—O2	−179.5 (2)	C8—C9—C10—C5	−0.1 (5)
C4—C5—C6—O2	1.1 (4)	C6—C5—C10—C9	−0.2 (4)
C10—C5—C6—C7	−0.5 (4)	C4—C5—C10—C9	179.2 (3)
C4—C5—C6—C7	−179.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.92	2.630 (3)	144
O3—H3···O2	0.82	2.24	2.689 (3)	115
O3—H3···O1ii	0.82	2.29	2.958 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.92	2.630 (3)	144
O3—H3⋯O2	0.82	2.24	2.689 (3)	115
O3—H3⋯O1i	0.82	2.29	2.958 (3)	139

Symmetry code: (i) .