6,6′-Dihydr­oxy-2,2′-[(pentane-1,5-diyl­dioxy)bis­(nitrilo­methyl­idyne)]diphenol

Dong, W.-K.; He, X.-N.; Guan, Y.-H.; Xu, L.; Ren, Z.-L.

doi:10.1107/S1600536808023064

organic compounds

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Volume 64| Part 8| August 2008| Pages o1600-o1601

doi:10.1107/S1600536808023064

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6,6′-Dihydroxy-2,2′-[(pentane-1,5-diyldioxy)bis(nitrilomethylidyne)]diphenol

Wen-Kui Dong,^a ^* Xue-Ni He,^a Yong-Hong Guan,^a Li Xu ^a and Zong-Li Ren ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: dongwk@mail.lzjtu.cn

(Received 18 July 2008; accepted 22 July 2008; online 26 July 2008)

The molecule of the title compound, C₁₉H₂₂N₂O₆, assumes a W-shaped configuration with the dihedral angle between the two halves of the molecule being 82.48 (5)°. There is one half-molecule 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—(CH₂)₅—O—N=CH—] bridge. The dihedral angle formed by the two benzene rings in each molecule of the title compound is 84.18 (4)°. There are strong intramolecular O—H⋯N and O—H⋯O hydrogen bonds and weak intermolecular π–π stacking interactions between neighbouring benzene rings, and the intermolecular plane-to-plane distances are 3.488 (2) and 3.841 (3) Å along the b and c axes, respectively. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link each molecule to two others, forming an infinite three-dimensional supramolecular 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_r = 374.39
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.135
S = 1.00
1621 reflections
123 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) $[x, -y, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023064/hg2427sup1.cif

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

checkCIF report

Comment top

Salen-type compounds are one of most versatile mixed-donor ligands in the field of coordination chemistry. There has been growing interest in salen-type ligands, mainly because of their wide application in the field of synthesis, biochemistry, photochemistry and catalysis (Akine et al., 2006; Atwood, 1997; Yu et al., 2008; Venkataramanan et al., 2005). Many salen-type complexes have been structurally characterized (Akine et al., 2006; Yu et al., 2008), but only a relatively small number of free salen-type compounds have been characterized (Akine et al., 2001). As an extension of our work (Dong & Feng, 2006; Duan et al., 2007; Dong, Zhao et al., 2008; Akine et al., 2005) on the structural characterization of salen-type bisoxime compounds, the title compound, (Fig. 1), is reported here.

The molecule assumes a W shape with the dihedral angle between the two halves of the molecule 82.48 (5)°. There is 1/2 molecule per asymmetric unit with a crystallographic twofold rotation axis passing through the central carbon (symmetry code: -x, y, 1/2 - z) of the five carbon atoms in the (—CH=N—O—(CH₂)₅—O—N═CH—) bridge. This structure is similar to what was observed in our previously reported salen-type bisoxime compound (Duan et al., 2007). The dihedral angle formed by the two benzene rings in each molecule of the title compound is 84.18 (4)°. There are strong intramolecular O—H···N and O—H···O hydrogen bonds and weak intermolecular π–π stacking interactions between the neighbouring benzene rings, and the inter-molecular plane-to-plane distances are 3.488 (2) and 3.841 (3) Å along b and c axis, respectively. In the crystal structure, intermolecular O—H···O hydrogen bonds link each molecule to 2 others into infinite three-dimensional supramolecular structure, which is the crystal structure firstly reported of salen-type bisoxime compounds containing pentamethene bridge.

Related literature top

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 top

6,6'-Dihydroxy-2,2'-[(pentane-1,5-diyldioxy)bis(nitrilomethylidyne)]diphenol was synthesized according to an analogous method reported earlier (Dong & Feng, 2006; Dong, He et al., 2008). To an ethanol solution (3 ml) of 2,3-dihydroxybenzaldehyde (138.4 mg, 1.0 mmol) was added an ethanol solution (2 ml) of 1,5-bis(aminooxy)pentane (67.4 mg, 0.5 mmol). The reaction mixture was stirred at 328 K for 8 h. After cooling to room temperature, the formed precipitate was separated by filtration, and washed successively with ethanol and ethanol–hexane (1:4), respectively. The product was dried under vacuum to yield 109.3 mg of the title compound. Yield, 58.4%. mp. 408.5–409.5 K. Anal. Calc. for C₁₉H₂₂N₂O₆: C, 60.95; H, 5.92; N, 7.48. Found: C, 60.75; H, 5.99; N, 7.42.

Pale-brown needle-like single crystals suitable for X-ray diffraction studies were obtained after two weeks by slow evaporation from a ethanol–chloroform mixed solution of the title compound.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with atom numbering scheme [Symmetry codes: -x + 1, y, -z + 3/2]. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
	Fig. 2. The W shape configuration of the title compound.
	Fig. 3. Part of the supramolecular structure of the title compound along b axis. Intra- and intermolecular hydrogen bonds are shown as dashed lines.

6,6'-Dihydroxy-2,2'-[(pentane-1,5-diyldioxy)bis(nitrilomethylidyne)]diphenol top

Crystal data top

C₁₉H₂₂N₂O₆	F(000) = 792
M_r = 374.39	D_x = 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 = 2.9–22.4°
b = 4.6997 (6) Å	µ = 0.10 mm⁻¹
c = 14.0843 (17) Å	T = 298 K
β = 100.354 (2)°	Needle-like, pale-brown
V = 1851.8 (4) Å³	0.46 × 0.27 × 0.25 mm
Z = 4

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	1621 independent reflections
Radiation source: fine-focus sealed tube	837 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −33→30
T_min = 0.955, T_max = 0.975	k = −5→5
4246 measured reflections	l = −16→16

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0407P)² + 1.5785P] where P = (F_o² + 2F_c²)/3
1621 reflections	(Δ/σ)_max < 0.001
123 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₉H₂₂N₂O₆	V = 1851.8 (4) Å³
M_r = 374.39	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 28.439 (3) Å	µ = 0.10 mm⁻¹
b = 4.6997 (6) Å	T = 298 K
c = 14.0843 (17) Å	0.46 × 0.27 × 0.25 mm
β = 100.354 (2)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	1621 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	837 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.975	R_int = 0.062
4246 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.00	Δρ_max = 0.24 e Å⁻³
1621 reflections	Δρ_min = −0.24 e Å⁻³
123 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) x, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₂N₂O₆
M_r	374.39
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	28.439 (3), 4.6997 (6), 14.0843 (17)
β (°)	100.354 (2)
V (Å³)	1851.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.46 × 0.27 × 0.25

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.955, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	4246, 1621, 837
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.135, 1.00
No. of reflections	1621
No. of parameters	123
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.24

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.92	2.630 (3)	144.4
O3—H3···O2	0.82	2.24	2.689 (3)	114.7
O3—H3···O1ⁱ	0.82	2.29	2.958 (3)	138.5

Symmetry code: (i) x, −y, z−1/2.

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (grant No. 0604-01) and the `Qing Lan' Talent Engineering Funds of Lanzhou Jiaotong University (grant No. QL-03-01A), which are gratefully acknowledged.

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

6,6′-Dihydr­­oxy-2,2′-[(pentane-1,5-diyl­di­oxy)bis­­(nitrilo­methyl­­idyne)]diphenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6,6′-Dihydroxy-2,2′-[(pentane-1,5-diyldioxy)bis(nitrilomethylidyne)]diphenol