2,2′-{1,1′-[Butane-1,4-diyl­bis(oxy­nitrilo)]di­ethylidyne}di-1-naphthol

Dong, W.-K.; Wu, J.-C.; Sun, Y.-X.; Yao, J.; Tong, J.-F.

doi:10.1107/S160053680901647X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1248

doi:10.1107/S160053680901647X

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2,2′-{1,1′-[Butane-1,4-diylbis(oxynitrilo)]diethylidyne}di-1-naphthol

Wen-Kui Dong,^a ^* Jian-Chao Wu,^a Yin-Xia Sun,^a Jian Yao ^a and Jun-Feng Tong ^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 28 April 2009; accepted 2 May 2009; online 14 May 2009)

The title compound, C₂₈H₂₈N₂O₄, was synthesized by the reaction of 2-acetyl-1-naphthol with 1,4-bis(aminooxy)butane in ethanol. The molecule, which lies about an inversion centre, adopts a linear structure, in which the oxime groups and naphthalene ring systems assume an anti conformation. The intramolecular interplanar distance between parallel naphthalene rings is 1.054 (3) Å. Intramolecular O—H⋯N hydrogen bonds are formed between the oxime nitrogen and hydroxy groups.

Related literature

For salen-type compounds, see: Atwood & Harvey (2001 ); Okabe & Oya (2000 ). For related structures, see: Dong et al. (2007 , 2008 ).

Experimental

Crystal data

C₂₈H₂₈N₂O₄
M_r = 456.52
Triclinic, $[P \overline 1]$
a = 6.9590 (15) Å
b = 8.6598 (18) Å
c = 10.596 (2) Å
α = 105.841 (2)°
β = 105.940 (2)°
γ = 91.689 (1)°
V = 586.9 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.50 × 0.43 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.958, T_max = 0.983
3020 measured reflections
2026 independent reflections
1350 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.173
S = 1.02
2026 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 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	2.557 (2)	145

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/S160053680901647X/hg2505sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901647X/hg2505Isup2.hkl

checkCIF report

Comment top

Salen-type compounds and their analogues are one of the most prevalent multidentate ligands in the field of modern coordination chemistry (Atwood & Harvey, 2001), which can coordinate to transition or rare earth ions yielding complexes with interesting properties that are useful in materials science and in biological systems (Okabe & Oya, 2000).

Herein, we report on the crystal structure of 2,2'-[(butane-1,4-diyldioxy)bis(nitriloethylidyne)]dinaphthol, shown in Fig. 1. The structure of the title compound consists of discrete C₂₈H₂₈N₂O₄ molecule, in which all bond lengths and angles are in normal ranges. The molecule is disposed about a crystallographic centre of symmetry with the (–CH═N—O-(CH)₄—O—N═CH–) bridge adopting a linear-shaped structure. The oxime groups and naphthalene rings assume an anti conformation. This structure is not similar to what was observed in our previously reported series salen-type compounds containing four-methene bridge, which often adopt an E configuration (Dong et al., 2007, 2008).

The two naphthalene rings in each molecule of the title compound are parallel and the distance between them is 1.054 (3) Å. Two intramolecular O—H···N hydrogen bonds are formed between the oxime nitrogen and hydroxy groups.

Related literature top

For salen-type compounds, see: Atwood & Harvey (2001); Okabe & Oya (2000). For related structures, see: Dong et al. (2007, 2008).

Experimental top

2,2'-[(Butane-1,4-diyldioxy)bis(nitriloethylidyne)]dinaphthol was synthesized according to our previous work (Dong et al., 2007). To an ethanol solution (5 ml) of 2-acetyl-1-naphthol (760.0 mg, 2.02 mmol) was added dropwise an ethanol solution (3 ml) of 1,4-bis(aminooxy)butane (243.0 mg, 1.01 mmol). The mixture solution was stirred at 328–333 K for 75 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 618.6 mg (yield 67.0%) of powder. Single crystals were obtained by slow evaporation from a solution of ethanol/dichloromethane (1:2) of 2,2'-[(butane-1,4-diyldioxy)bis(nitriloethylidyne)]dinaphthol at room temperature for several weeks. Anal. Calcd. for C₂₈H₂₈N₂O₄: C, 73.66; H, 6.18; N, 6.14; Found: C, 73.61; H, 6.23; N, 6.09%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (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 molecule structure of the title compound with atom numbering [Symmetry codes: -x + 1, -y + 1, -z]. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.

2,2'-{1,1'-[Butane-1,4-diylbis(oxynitrilo)]diethylidyne}di-1-naphthol top

Crystal data top

C₂₈H₂₈N₂O₄	Z = 1
M_r = 456.52	F(000) = 242
Triclinic, P1	D_x = 1.292 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9590 (15) Å	Cell parameters from 1246 reflections
b = 8.6598 (18) Å	θ = 2.5–27.6°
c = 10.596 (2) Å	µ = 0.09 mm⁻¹
α = 105.841 (2)°	T = 298 K
β = 105.940 (2)°	Block, pale-yellow
γ = 91.689 (1)°	0.50 × 0.43 × 0.20 mm
V = 586.9 (2) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2026 independent reflections
Radiation source: fine-focus sealed tube	1350 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.958, T_max = 0.983	k = −9→10
3020 measured reflections	l = −12→6

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.096P)² + 0.0813P] where P = (F_o² + 2F_c²)/3
2026 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₈H₂₈N₂O₄	γ = 91.689 (1)°
M_r = 456.52	V = 586.9 (2) Å³
Triclinic, P1	Z = 1
a = 6.9590 (15) Å	Mo Kα radiation
b = 8.6598 (18) Å	µ = 0.09 mm⁻¹
c = 10.596 (2) Å	T = 298 K
α = 105.841 (2)°	0.50 × 0.43 × 0.20 mm
β = 105.940 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2026 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1350 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.983	R_int = 0.025
3020 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.02	Δρ_max = 0.23 e Å⁻³
2026 reflections	Δρ_min = −0.25 e Å⁻³
154 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	0.4299 (3)	0.3289 (2)	0.31934 (16)	0.0435 (5)
O1	0.3505 (2)	0.37340 (18)	0.19981 (14)	0.0515 (5)
O2	0.7182 (2)	0.30688 (18)	0.52155 (15)	0.0505 (5)
H2	0.6665	0.3326	0.4519	0.076*
C1	0.5112 (3)	0.4251 (3)	0.1562 (2)	0.0455 (6)
H1A	0.5966	0.3396	0.1410	0.055*
H1B	0.5923	0.5189	0.2259	0.055*
C2	0.4211 (3)	0.4667 (3)	0.0252 (2)	0.0449 (6)
H2A	0.3277	0.5459	0.0400	0.054*
H2B	0.3460	0.3705	−0.0449	0.054*
C3	0.2958 (3)	0.2877 (2)	0.3702 (2)	0.0402 (5)
C4	0.0759 (3)	0.2939 (3)	0.3091 (2)	0.0627 (7)
H4A	0.0578	0.3501	0.2408	0.094*
H4B	0.0198	0.3496	0.3798	0.094*
H4C	0.0091	0.1859	0.2673	0.094*
C5	0.5732 (3)	0.2467 (2)	0.5630 (2)	0.0372 (5)
C6	0.3690 (3)	0.2344 (2)	0.49419 (19)	0.0365 (5)
C7	0.2306 (3)	0.1639 (2)	0.5453 (2)	0.0433 (5)
H7	0.0937	0.1554	0.5009	0.052*
C8	0.2912 (3)	0.1088 (2)	0.6565 (2)	0.0438 (6)
H8	0.1961	0.0608	0.6851	0.053*
C9	0.4976 (3)	0.1238 (2)	0.7294 (2)	0.0386 (5)
C10	0.6397 (3)	0.1961 (2)	0.6838 (2)	0.0370 (5)
C11	0.8449 (3)	0.2185 (3)	0.7606 (2)	0.0506 (6)
H11	0.9400	0.2668	0.7321	0.061*
C12	0.9047 (4)	0.1696 (3)	0.8761 (3)	0.0600 (7)
H12	1.0397	0.1872	0.9270	0.072*
C13	0.7640 (4)	0.0933 (3)	0.9182 (2)	0.0564 (7)
H13	0.8068	0.0574	0.9955	0.068*
C14	0.5661 (3)	0.0711 (3)	0.8475 (2)	0.0479 (6)
H14	0.4743	0.0207	0.8770	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0575 (12)	0.0489 (11)	0.0329 (9)	0.0084 (9)	0.0176 (8)	0.0215 (8)
O1	0.0585 (10)	0.0695 (11)	0.0386 (8)	0.0082 (8)	0.0167 (7)	0.0329 (7)
O2	0.0468 (9)	0.0664 (10)	0.0556 (10)	0.0120 (7)	0.0240 (7)	0.0362 (8)
C1	0.0570 (13)	0.0519 (13)	0.0402 (12)	0.0112 (10)	0.0242 (10)	0.0234 (10)
C2	0.0573 (14)	0.0482 (12)	0.0360 (12)	0.0094 (11)	0.0180 (10)	0.0188 (9)
C3	0.0498 (12)	0.0394 (11)	0.0345 (11)	0.0036 (9)	0.0159 (9)	0.0121 (9)
C4	0.0544 (15)	0.0897 (19)	0.0525 (14)	0.0030 (13)	0.0111 (11)	0.0397 (13)
C5	0.0447 (12)	0.0363 (11)	0.0393 (11)	0.0080 (9)	0.0219 (9)	0.0152 (9)
C6	0.0443 (12)	0.0380 (11)	0.0313 (10)	0.0048 (9)	0.0155 (9)	0.0124 (8)
C7	0.0434 (12)	0.0523 (13)	0.0374 (11)	0.0003 (10)	0.0131 (9)	0.0178 (10)
C8	0.0487 (13)	0.0495 (13)	0.0404 (12)	−0.0015 (10)	0.0203 (10)	0.0182 (10)
C9	0.0505 (13)	0.0354 (11)	0.0375 (11)	0.0105 (9)	0.0202 (9)	0.0149 (9)
C10	0.0438 (12)	0.0367 (11)	0.0379 (11)	0.0138 (9)	0.0177 (9)	0.0157 (9)
C11	0.0466 (13)	0.0589 (14)	0.0597 (14)	0.0164 (11)	0.0218 (11)	0.0315 (11)
C12	0.0498 (14)	0.0742 (17)	0.0654 (16)	0.0220 (12)	0.0132 (12)	0.0376 (13)
C13	0.0643 (16)	0.0638 (15)	0.0534 (14)	0.0232 (12)	0.0170 (12)	0.0356 (12)
C14	0.0621 (15)	0.0493 (13)	0.0455 (13)	0.0138 (11)	0.0239 (11)	0.0262 (10)

Geometric parameters (Å, º) top

N1—C3	1.285 (3)	C5—C10	1.427 (3)
N1—O1	1.398 (2)	C6—C7	1.423 (3)
O1—C1	1.425 (2)	C7—C8	1.357 (3)
O2—C5	1.350 (2)	C7—H7	0.9300
O2—H2	0.8200	C8—C9	1.415 (3)
C1—C2	1.503 (3)	C8—H8	0.9300
C1—H1A	0.9700	C9—C10	1.413 (3)
C1—H1B	0.9700	C9—C14	1.414 (3)
C2—C2ⁱ	1.509 (4)	C10—C11	1.414 (3)
C2—H2A	0.9700	C11—C12	1.365 (3)
C2—H2B	0.9700	C11—H11	0.9300
C3—C6	1.475 (3)	C12—C13	1.400 (3)
C3—C4	1.498 (3)	C12—H12	0.9300
C4—H4A	0.9600	C13—C14	1.354 (3)
C4—H4B	0.9600	C13—H13	0.9300
C4—H4C	0.9600	C14—H14	0.9300
C5—C6	1.394 (3)

C3—N1—O1	113.72 (17)	C5—C6—C7	117.71 (18)
N1—O1—C1	109.26 (15)	C5—C6—C3	122.01 (18)
C5—O2—H2	109.5	C7—C6—C3	120.26 (18)
O1—C1—C2	107.96 (18)	C8—C7—C6	122.4 (2)
O1—C1—H1A	110.1	C8—C7—H7	118.8
C2—C1—H1A	110.1	C6—C7—H7	118.8
O1—C1—H1B	110.1	C7—C8—C9	120.59 (19)
C2—C1—H1B	110.1	C7—C8—H8	119.7
H1A—C1—H1B	108.4	C9—C8—H8	119.7
C1—C2—C2ⁱ	112.2 (2)	C10—C9—C14	118.88 (19)
C1—C2—H2A	109.2	C10—C9—C8	118.87 (17)
C2ⁱ—C2—H2A	109.2	C14—C9—C8	122.24 (19)
C1—C2—H2B	109.2	C9—C10—C11	118.88 (18)
C2ⁱ—C2—H2B	109.2	C9—C10—C5	119.50 (18)
H2A—C2—H2B	107.9	C11—C10—C5	121.61 (19)
N1—C3—C6	116.56 (18)	C12—C11—C10	120.5 (2)
N1—C3—C4	122.53 (18)	C12—C11—H11	119.8
C6—C3—C4	120.91 (18)	C10—C11—H11	119.8
C3—C4—H4A	109.5	C11—C12—C13	120.4 (2)
C3—C4—H4B	109.5	C11—C12—H12	119.8
H4A—C4—H4B	109.5	C13—C12—H12	119.8
C3—C4—H4C	109.5	C14—C13—C12	120.6 (2)
H4A—C4—H4C	109.5	C14—C13—H13	119.7
H4B—C4—H4C	109.5	C12—C13—H13	119.7
O2—C5—C6	122.92 (17)	C13—C14—C9	120.8 (2)
O2—C5—C10	116.22 (18)	C13—C14—H14	119.6
C6—C5—C10	120.86 (18)	C9—C14—H14	119.6

C3—N1—O1—C1	176.83 (17)	C7—C8—C9—C14	178.56 (19)
N1—O1—C1—C2	178.10 (15)	C14—C9—C10—C11	−2.1 (3)
O1—C1—C2—C2ⁱ	176.3 (2)	C8—C9—C10—C11	176.85 (18)
O1—N1—C3—C6	178.15 (15)	C14—C9—C10—C5	178.64 (16)
O1—N1—C3—C4	−2.3 (3)	C8—C9—C10—C5	−2.4 (3)
O2—C5—C6—C7	177.98 (17)	O2—C5—C10—C9	−176.58 (16)
C10—C5—C6—C7	−2.5 (3)	C6—C5—C10—C9	3.8 (3)
O2—C5—C6—C3	−0.4 (3)	O2—C5—C10—C11	4.2 (3)
C10—C5—C6—C3	179.16 (17)	C6—C5—C10—C11	−175.34 (18)
N1—C3—C6—C5	7.8 (3)	C9—C10—C11—C12	0.5 (3)
C4—C3—C6—C5	−171.77 (19)	C5—C10—C11—C12	179.74 (19)
N1—C3—C6—C7	−170.53 (17)	C10—C11—C12—C13	1.5 (4)
C4—C3—C6—C7	9.9 (3)	C11—C12—C13—C14	−2.0 (4)
C5—C6—C7—C8	−0.4 (3)	C12—C13—C14—C9	0.3 (3)
C3—C6—C7—C8	178.04 (18)	C10—C9—C14—C13	1.7 (3)
C6—C7—C8—C9	1.8 (3)	C8—C9—C14—C13	−177.2 (2)
C7—C8—C9—C10	−0.4 (3)

Symmetry code: (i) −x+1, −y+1, −z.

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	2.557 (2)	145

Experimental details

Crystal data
Chemical formula	C₂₈H₂₈N₂O₄
M_r	456.52
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.9590 (15), 8.6598 (18), 10.596 (2)
α, β, γ (°)	105.841 (2), 105.940 (2), 91.689 (1)
V (Å³)	586.9 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.43 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.958, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	3020, 2026, 1350
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.173, 1.02
No. of reflections	2026
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.25

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	2.557 (2)	145.0

Acknowledgements

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

References

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