2,2′-[1,1′-(Ethyl­enedioxy­dinitrilo)diethyl­idyne]di-1-naphthol

Dong, W.-K.; Wu, J.; Yao, J.; Li, L.; Gong, S.

doi:10.1107/S1600536809022508

organic compounds

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Volume 65| Part 7| July 2009| Page o1598

doi:10.1107/S1600536809022508

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2,2′-[1,1′-(Ethylenedioxydinitrilo)diethylidyne]di-1-naphthol

Wen-Kui Dong,^a ^* Jian-chao Wu,^a Jian Yao,^a Li Li ^a and Shang-sheng Gong ^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 11 June 2009; accepted 12 June 2009; online 17 June 2009)

The complete molecule of the title compound, C₂₆H₂₄N₂O₄, is generated by a crystallographic centre of inversion. There are two intramolecular O—H⋯N hydrogen bonds. In the crystal structure, intermolecular C—H⋯O hydrogen bonds result in zigzag chains.

Related literature

For the applications of Shiff base ligands, see: Calligaris & Randaccio (1987 ) For the applications bisoxime derivatives of salen-type compounds, see: Sun et al. (2004 ); Wang et al. (2007 ). For related structures, see: Dong et al. (2008a ,b ,c );

Experimental

Crystal data

C₂₆H₂₄N₂O₄
M_r = 428.47
Monoclinic, C 2/c
a = 12.6682 (18) Å
b = 9.3728 (15) Å
c = 18.335 (2) Å
β = 97.478 (2)°
V = 2158.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.39 × 0.37 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.966, T_max = 0.989
5220 measured reflections
1894 independent reflections
1027 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.122
S = 1.06
1894 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 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	1.84	2.562 (3)	146
C10—H10⋯O2ⁱ	0.93	2.63	3.446 (3)	146
Symmetry code: (i) $[-x+{\script{3\over 2}}, -y-{\script{1\over 2}}, -z+1]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022508/hg2524sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022508/hg2524Isup2.hkl

checkCIF report

Comment top

There has been considerable interest in Schiff base ligand containing oxygen and imine nitrogen atoms due to their variety of applications, especially for catalysis and enzymatic reactions, magnetism, and supramolecular architectures (Calligaris & Randaccio, 1987). salen-type compounds and its bisoxime derivatives are a new class of multidentate ligand, which can be used as elemental building blocks for construction of supramolecular structures via intermolecular hydrogen bonding or short contact interaction (Sun et al., 2004; Wang et al., 2007). As an extension of our work (Dong et al., 2008a; Dong et al., 2008b) on the structural characterization of salen-type bisoxime compounds, here report the synthesis and structure of the title compound (Fig. 1).

The single-crystal structure of the title compound is built up by discrete C₂₆H₂₄N₂O₄ molecules, in which all bond lengths are in normal ranges. The molecule has a crystallographic twofold rotation axis (symmetry code: -x, y, 1/2 - z) and screw axis (symmetry code: 1/2 - x, 1/2 + y, 1/2 - z), and adopts a distorted E-configuration. This structure is similar to what was observed in our previously reported E-configuration compounds of 2,2'-[1,1'-Ethylenedioxybis(nitriloethylidyne)]diphenol (Wang et al., 2007). The dihedral angle formed by the two naphthalene rings in each molecule of the title compound is about 43.20 °. There are two intramolecular hydrogen bonds, O2—H2···N1 (d(O2—H2) = 0.82 Å, d(H2···N1) = 1.84 Å, d(O2···N1) = 2.562 (3) Å, <O2—H2···N1 = 146°). Besides in the crystal structure, four intermolecular hydrogen bonds, C10—H10···O2 (d(C10—H10) = 0.93 Å, d(H10···O2) = 2.63 Å, d(C10···O2) = 3.446 (3) Å, <C10—H10···O2 = 146°), link two other molecules into infinite zigzag supramolecular structure (Fig. 2).

Related literature top

For the applications of Shiff base ligands, see: Calligaris & Randaccio (1987) For the applications bisoxime derivatives of salen-type compounds, see: Sun et al. (2004); Wang et al. (2007). For related structures, see: Dong et al. (2008a,b,c);

Experimental top

2,2'-[1,1'-Ethylenedioxybis(nitriloethylidyne)]dinaphthol was synthesized according to an analogous method reported earlier (Dong et al., 2008c). To an ethanol solution (5 ml) of 2-acetyl-1-naphthol (392.1 mg, 2.10 mmol) was added dropwise an ethanol solution (3 ml) of 1,2-bis(aminooxy)ethane (96.2 mg, 1.04 mmol). The mixture solution was stirred at 328–433 K for 72 h. After cooling to room temperature, the precipitate was filtered off, and washed successively three times with ethanol. The product was dried in vacuo and purified by recrystallization from ethanol to yield 313.7 mg (Yield, 70.1%) of powder; m.p. 471–472 K. Colorless block-like single crystals suitable for X-ray diffraction studies were obtained by slow evaporation from a solution of dichloromethane of 2,2'-[1,1'-ethylenedioxybis(nitriloethylidyne)]dinaphthol at room temperature for about three weeks. Anal. Calc. for C₂₆H₂₄N₂O₄: C, 73.28; H, 5.92; N, 6.33; Found: C, 73.25; H, 5.97; N, 6.29.

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+2, y, -z + 3/2]. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
	Fig. 2. Part of the supramolecular structure of the title compound. Intra- and intermolecular hydrogen bonds are shown as dashed lines.

2,2'-[1,1'-(Ethylenedioxydinitrilo)diethylidyne]di-1-naphthol top

Crystal data top

C₂₆H₂₄N₂O₄	F(000) = 904
M_r = 428.47	D_x = 1.318 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1610 reflections
a = 12.6682 (18) Å	θ = 2.2–26.7°
b = 9.3728 (15) Å	µ = 0.09 mm⁻¹
c = 18.335 (2) Å	T = 298 K
β = 97.478 (2)°	Block-shaped, colorless
V = 2158.6 (5) Å³	0.39 × 0.37 × 0.13 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1894 independent reflections
Radiation source: fine-focus sealed tube	1027 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→14
T_min = 0.966, T_max = 0.989	k = −11→9
5220 measured reflections	l = −18→21

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.037P)² + 1.5505P] where P = (F_o² + 2F_c²)/3
1894 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₆H₂₄N₂O₄	V = 2158.6 (5) Å³
M_r = 428.47	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 12.6682 (18) Å	µ = 0.09 mm⁻¹
b = 9.3728 (15) Å	T = 298 K
c = 18.335 (2) Å	0.39 × 0.37 × 0.13 mm
β = 97.478 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1894 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1027 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.989	R_int = 0.035
5220 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.06	Δρ_max = 0.14 e Å⁻³
1894 reflections	Δρ_min = −0.15 e Å⁻³
145 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
N1	0.97510 (17)	0.0879 (2)	0.61829 (11)	0.0528 (6)
O1	1.04967 (14)	0.11327 (19)	0.68140 (9)	0.0610 (5)
O2	0.84279 (14)	−0.06506 (17)	0.53429 (9)	0.0620 (6)
H2	0.8831	−0.0456	0.5717	0.093*
C1	1.0479 (2)	−0.0049 (3)	0.73030 (14)	0.0567 (7)
H1A	1.1113	−0.0024	0.7661	0.068*
H1B	1.0493	−0.0929	0.7025	0.068*
C2	0.9707 (2)	0.1902 (3)	0.57048 (14)	0.0500 (7)
C3	1.0376 (2)	0.3226 (3)	0.58230 (16)	0.0714 (9)
H3A	1.0938	0.3072	0.6220	0.107*
H3B	0.9941	0.4009	0.5942	0.107*
H3C	1.0678	0.3444	0.5382	0.107*
C4	0.83740 (19)	0.0469 (3)	0.48738 (13)	0.0464 (6)
C5	0.89572 (19)	0.1710 (2)	0.50274 (12)	0.0469 (6)
C6	0.8818 (2)	0.2819 (3)	0.44918 (15)	0.0610 (8)
H6	0.9202	0.3660	0.4582	0.073*
C7	0.8146 (2)	0.2692 (3)	0.38547 (16)	0.0676 (8)
H7	0.8065	0.3454	0.3527	0.081*
C8	0.7568 (2)	0.1424 (3)	0.36816 (14)	0.0552 (7)
C9	0.7676 (2)	0.0289 (3)	0.42035 (13)	0.0490 (7)
C10	0.7106 (2)	−0.0991 (3)	0.40331 (15)	0.0632 (8)
H10	0.7163	−0.1737	0.4370	0.076*
C11	0.6470 (2)	−0.1137 (4)	0.33734 (18)	0.0774 (9)
H11	0.6097	−0.1982	0.3266	0.093*
C12	0.6378 (2)	−0.0025 (4)	0.28598 (17)	0.0794 (10)
H12	0.5957	−0.0146	0.2409	0.095*
C13	0.6896 (2)	0.1227 (4)	0.30122 (15)	0.0707 (9)
H13	0.6807	0.1966	0.2671	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0581 (14)	0.0524 (13)	0.0491 (13)	−0.0069 (11)	0.0112 (11)	−0.0060 (11)
O1	0.0618 (12)	0.0706 (13)	0.0511 (11)	−0.0170 (10)	0.0085 (9)	−0.0068 (9)
O2	0.0768 (13)	0.0463 (10)	0.0591 (12)	−0.0120 (9)	−0.0055 (10)	0.0078 (9)
C1	0.0569 (18)	0.0582 (17)	0.0548 (17)	0.0022 (13)	0.0063 (13)	−0.0011 (14)
C2	0.0553 (16)	0.0410 (14)	0.0572 (17)	−0.0059 (13)	0.0205 (13)	−0.0099 (13)
C3	0.085 (2)	0.0560 (18)	0.076 (2)	−0.0235 (16)	0.0195 (17)	−0.0080 (15)
C4	0.0559 (17)	0.0381 (14)	0.0474 (15)	0.0028 (12)	0.0152 (13)	0.0019 (12)
C5	0.0582 (16)	0.0398 (14)	0.0458 (15)	−0.0022 (13)	0.0176 (13)	−0.0033 (12)
C6	0.080 (2)	0.0431 (15)	0.0637 (19)	−0.0059 (15)	0.0249 (16)	0.0047 (14)
C7	0.086 (2)	0.0622 (19)	0.0587 (19)	0.0079 (17)	0.0262 (17)	0.0161 (15)
C8	0.0593 (18)	0.0602 (18)	0.0491 (16)	0.0143 (15)	0.0180 (14)	0.0030 (14)
C9	0.0485 (16)	0.0489 (16)	0.0509 (16)	0.0069 (13)	0.0117 (13)	−0.0021 (13)
C10	0.0617 (18)	0.0606 (18)	0.0659 (19)	−0.0008 (15)	0.0034 (16)	−0.0052 (15)
C11	0.064 (2)	0.087 (2)	0.079 (2)	−0.0027 (18)	−0.0008 (18)	−0.0190 (19)
C12	0.061 (2)	0.116 (3)	0.059 (2)	0.016 (2)	0.0015 (16)	−0.012 (2)
C13	0.065 (2)	0.094 (2)	0.0537 (19)	0.0235 (19)	0.0121 (16)	0.0088 (17)

Geometric parameters (Å, º) top

N1—C2	1.295 (3)	C5—C6	1.425 (3)
N1—O1	1.415 (2)	C6—C7	1.358 (3)
O1—C1	1.427 (3)	C6—H6	0.9300
O2—C4	1.353 (3)	C7—C8	1.410 (4)
O2—H2	0.8200	C7—H7	0.9300
C1—C1ⁱ	1.490 (5)	C8—C13	1.412 (4)
C1—H1A	0.9700	C8—C9	1.426 (3)
C1—H1B	0.9700	C9—C10	1.413 (3)
C2—C5	1.473 (3)	C10—C11	1.370 (3)
C2—C3	1.504 (3)	C10—H10	0.9300
C3—H3A	0.9600	C11—C12	1.400 (4)
C3—H3B	0.9600	C11—H11	0.9300
C3—H3C	0.9600	C12—C13	1.355 (4)
C4—C5	1.387 (3)	C12—H12	0.9300
C4—C9	1.428 (3)	C13—H13	0.9300

C2—N1—O1	113.2 (2)	C7—C6—C5	122.5 (3)
N1—O1—C1	108.64 (18)	C7—C6—H6	118.8
C4—O2—H2	109.5	C5—C6—H6	118.8
O1—C1—C1ⁱ	112.64 (18)	C6—C7—C8	121.1 (3)
O1—C1—H1A	109.1	C6—C7—H7	119.5
C1ⁱ—C1—H1A	109.1	C8—C7—H7	119.5
O1—C1—H1B	109.1	C7—C8—C13	122.9 (3)
C1ⁱ—C1—H1B	109.1	C7—C8—C9	118.4 (2)
H1A—C1—H1B	107.8	C13—C8—C9	118.7 (3)
N1—C2—C5	116.6 (2)	C10—C9—C8	118.9 (2)
N1—C2—C3	122.7 (2)	C10—C9—C4	122.1 (2)
C5—C2—C3	120.8 (2)	C8—C9—C4	118.9 (2)
C2—C3—H3A	109.5	C11—C10—C9	120.3 (3)
C2—C3—H3B	109.5	C11—C10—H10	119.8
H3A—C3—H3B	109.5	C9—C10—H10	119.8
C2—C3—H3C	109.5	C10—C11—C12	120.5 (3)
H3A—C3—H3C	109.5	C10—C11—H11	119.8
H3B—C3—H3C	109.5	C12—C11—H11	119.8
O2—C4—C5	122.7 (2)	C13—C12—C11	120.7 (3)
O2—C4—C9	115.4 (2)	C13—C12—H12	119.7
C5—C4—C9	121.9 (2)	C11—C12—H12	119.7
C4—C5—C6	117.2 (2)	C12—C13—C8	120.9 (3)
C4—C5—C2	122.8 (2)	C12—C13—H13	119.6
C6—C5—C2	120.1 (2)	C8—C13—H13	119.6

C2—N1—O1—C1	179.8 (2)	C6—C7—C8—C9	2.2 (4)
N1—O1—C1—C1ⁱ	−75.0 (3)	C7—C8—C9—C10	−179.5 (2)
O1—N1—C2—C5	179.31 (19)	C13—C8—C9—C10	−0.1 (4)
O1—N1—C2—C3	−0.8 (3)	C7—C8—C9—C4	−0.9 (3)
O2—C4—C5—C6	−179.2 (2)	C13—C8—C9—C4	178.5 (2)
C9—C4—C5—C6	1.1 (3)	O2—C4—C9—C10	−1.9 (3)
O2—C4—C5—C2	1.7 (4)	C5—C4—C9—C10	177.9 (2)
C9—C4—C5—C2	−178.1 (2)	O2—C4—C9—C8	179.6 (2)
N1—C2—C5—C4	−4.3 (3)	C5—C4—C9—C8	−0.7 (3)
C3—C2—C5—C4	175.8 (2)	C8—C9—C10—C11	0.6 (4)
N1—C2—C5—C6	176.6 (2)	C4—C9—C10—C11	−177.9 (2)
C3—C2—C5—C6	−3.3 (4)	C9—C10—C11—C12	0.1 (4)
C4—C5—C6—C7	0.2 (4)	C10—C11—C12—C13	−1.5 (5)
C2—C5—C6—C7	179.3 (2)	C11—C12—C13—C8	2.1 (5)
C5—C6—C7—C8	−1.8 (4)	C7—C8—C13—C12	178.1 (3)
C6—C7—C8—C13	−177.2 (3)	C9—C8—C13—C12	−1.3 (4)

Symmetry code: (i) −x+2, 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	1.84	2.562 (3)	146
C10—H10···O2ⁱⁱ	0.93	2.63	3.446 (3)	146

Symmetry code: (ii) −x+3/2, −y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₄N₂O₄
M_r	428.47
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	12.6682 (18), 9.3728 (15), 18.335 (2)
β (°)	97.478 (2)
V (Å³)	2158.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.39 × 0.37 × 0.13

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.966, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	5220, 1894, 1027
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.122, 1.06
No. of reflections	1894
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.15

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	1.84	2.562 (3)	145.7
C10—H10···O2ⁱ	0.93	2.63	3.446 (3)	146.3

Symmetry code: (i) −x+3/2, −y−1/2, −z+1.

Acknowledgements

The authors acknowledge finanical support from the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University.

References

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