1,1′-[(Hexane-1,6-diyldi­oxy)bis­(nitrilo­methyl­idyne)]dinaphthalene

Dong, W.-K.; He, X.-N.; Li, L.; Lv, Z.-W.; Tong, J.-F.

doi:10.1107/S160053680801920X

organic compounds

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Volume 64| Part 8| August 2008| Page o1405

doi:10.1107/S160053680801920X

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1,1′-[(Hexane-1,6-diyldioxy)bis(nitrilomethylidyne)]dinaphthalene

Wen-Kui Dong,^a ^* Xue-Ni He,^a Li Li,^a Zhong-Wu Lv ^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 16 June 2008; accepted 24 June 2008; online 5 July 2008)

The title compound, C₂₈H₂₈N₂O₂, was synthesized by condensation of 1-naphthaldehyde with 1,6-bis(aminooxy)hexane in ethanol. The molecule is disposed about a crystallographic centre of symmetry. In the crystal structure, molecules are linked through strong intermolecular π–π stacking interactions [interplana distance = 2.986 (2) Å], forming a three-dimensional network.

Related literature

For related literature, see: Akine et al. (2006 ); Dong et al. (2007 ); Herzfeld & Nagy (1999 ); Shi et al. (2007 ); You et al. (2004 ).

Experimental

Crystal data

C₂₈H₂₈N₂O₂
M_r = 424.52
Monoclinic, P 2₁ /c
a = 9.2925 (16) Å
b = 6.3938 (12) Å
c = 19.723 (2) Å
β = 96.489 (2)°
V = 1164.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.47 × 0.42 × 0.23 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.965, T_max = 0.983
5470 measured reflections
2050 independent reflections
1047 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.154
S = 1.07
2050 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.12 e Å⁻³

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/S160053680801920X/hg2416sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801920X/hg2416Isup2.hkl

checkCIF report

Comment top

Schiff-base compounds containing imine groups have been used as modulators of structural and electronic properties of transition matal centres in modern coordination chemistry (You, et al., 2004). The diversity in the coordination environment and structures of transition metal complexes mainly depend on the type of Schiff-base ligands (Herzfeld, et al., 1999). In this research, we report on the synthesis and crystal structure of (I) with the aim of confirming its structural properties, and gaining further insight into its coordinating abilities toward various transition metal ions.

The crystal structure of (I) consists of discrete molecules disposed about a crystallographic centre of symmetry. The six carbon atoms in the (—CH=N—O—(CH₂)₆—O—N=CH—) bridge deviate slightly from the mean plane, with C1, C2 and C3 above by 0.04, 0.04 and 0.08 Å, and C1A, C2A and C3A below by 0.04, 0.04 and 0.08 Å (symmetry code A: -x + 1, -y, -z), respectively. The planes of the two naphthane rings in (I) are parallel with a separation distance of 2.163 (2) Å. In the crystal structure, molecules are linked through strong intermolecular π–π stacking interactions (Inter-molecular plane-to-plane distance, 2.986 (2) Å) to form a three-dimensional network.

Related literature top

For related literature, see: Akine et al. (2006); Dong et al. (2007); Herzfeld & Nagy (1999); Shi et al. (2007); You et al. (2004).

Experimental top

1,1'-[Hexane-1,6-diyldioxybis(nitrilomethylidyne)]dinaphthalene was synthesized according to an analogous method reported earlier (Shi, et al., 2007; Akine, et al., 2006; Dong, et al., 2007). To an ethanol solution (5 ml) of 1-naphthaldehyde (644.1 mg, 4.00 mmol) was added an ethanol solution (5 ml) of 1, 6-bis(aminooxy)hexane (296.5 mg, 2.00 mmol). The mixed solution was stirred at 328 K for 5 h. When cooled to room temperature, the precipitate was filtered, and washed successively with ethanol and hexane, respectively. The product was dried under vacuum and purified with recrystallization from ethanol to yield 637.4 mg of (I). Yield, 75.1%. mp. 348–349 K. Anal. Calc. for C₂₈H₂₈N₂O₂: C, 79.22; H, 6.65; N, 6.60. Found: C, 79.35; H, 6.75; N, 6.53.

Colorless block-shaped single crystals suitable for X-ray diffraction studies were obtained after several weeks by slow evaporation from an methanol solution of (I).

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 molecule structure of (I) with atom numbering (symmetry code A: -x + 1, -y, -z). Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
	Fig. 2. Crystal structure of (I) showing the formation of π–π interactions (Inter-molecular plane-to-plane distance, 2.986 (2) Å).

1,1'-[(Hexane-1,6-diyldioxy)bis(nitrilomethylidyne)]dinaphthalene top

Crystal data top

C₂₈H₂₈N₂O₂	F(000) = 452
M_r = 424.52	D_x = 1.211 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1078 reflections
a = 9.2925 (16) Å	θ = 2.2–22.9°
b = 6.3938 (12) Å	µ = 0.08 mm⁻¹
c = 19.723 (2) Å	T = 298 K
β = 96.489 (2)°	Block-shaped, colorless
V = 1164.3 (3) Å³	0.47 × 0.42 × 0.23 mm
Z = 2

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2050 independent reflections
Radiation source: fine-focus sealed tube	1047 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.965, T_max = 0.983	k = −7→3
5470 measured reflections	l = −22→23

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + 0.4185P] where P = (F_o² + 2F_c²)/3
2050 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₂₈H₂₈N₂O₂	V = 1164.3 (3) Å³
M_r = 424.52	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.2925 (16) Å	µ = 0.08 mm⁻¹
b = 6.3938 (12) Å	T = 298 K
c = 19.723 (2) Å	0.47 × 0.42 × 0.23 mm
β = 96.489 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2050 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1047 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.983	R_int = 0.040
5470 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.08	Δρ_max = 0.18 e Å⁻³
2050 reflections	Δρ_min = −0.12 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	0.2373 (3)	0.6843 (4)	0.09525 (11)	0.0619 (7)
O1	0.2359 (2)	0.5082 (3)	0.05242 (10)	0.0696 (6)
C1	0.3666 (3)	0.3957 (4)	0.06716 (14)	0.0599 (8)
H1A	0.3749	0.3439	0.1137	0.072*
H1B	0.4486	0.4861	0.0624	0.072*
C2	0.3651 (3)	0.2176 (5)	0.01842 (14)	0.0608 (8)
H2A	0.3492	0.2722	−0.0277	0.073*
H2B	0.2840	0.1272	0.0250	0.073*
C3	0.5006 (3)	0.0891 (4)	0.02526 (13)	0.0633 (9)
H3A	0.5156	0.0321	0.0711	0.076*
H3B	0.5820	0.1798	0.0195	0.076*
C4	0.1146 (4)	0.7770 (5)	0.08649 (13)	0.0580 (8)
H4	0.0423	0.7156	0.0565	0.070*
C5	0.0789 (3)	0.9699 (5)	0.11943 (13)	0.0526 (7)
C6	−0.0446 (3)	1.0682 (5)	0.09222 (15)	0.0658 (9)
H6	−0.1010	1.0040	0.0562	0.079*
C7	−0.0904 (4)	1.2583 (6)	0.11549 (17)	0.0755 (10)
H7	−0.1745	1.3205	0.0947	0.091*
C8	−0.0126 (4)	1.3520 (5)	0.16820 (17)	0.0721 (10)
H8	−0.0436	1.4792	0.1842	0.086*
C9	0.1160 (3)	1.2596 (5)	0.19969 (14)	0.0562 (8)
C10	0.1637 (3)	1.0647 (5)	0.17612 (13)	0.0498 (7)
C11	0.2900 (3)	0.9759 (5)	0.21026 (14)	0.0661 (9)
H11	0.3231	0.8479	0.1959	0.079*
C12	0.3639 (4)	1.0755 (7)	0.26392 (17)	0.0859 (11)
H12	0.4470	1.0142	0.2861	0.103*
C13	0.3182 (5)	1.2668 (7)	0.28634 (18)	0.0911 (12)
H13	0.3713	1.3338	0.3228	0.109*
C14	0.1975 (4)	1.3554 (6)	0.25544 (18)	0.0798 (11)
H14	0.1672	1.4832	0.2713	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0736 (19)	0.0517 (16)	0.0629 (16)	−0.0071 (14)	0.0189 (13)	−0.0125 (13)
O1	0.0779 (15)	0.0602 (14)	0.0711 (13)	0.0002 (12)	0.0109 (11)	−0.0154 (12)
C1	0.067 (2)	0.0532 (19)	0.0614 (18)	−0.0088 (17)	0.0143 (15)	−0.0052 (16)
C2	0.071 (2)	0.0524 (18)	0.0598 (18)	−0.0114 (17)	0.0115 (15)	−0.0068 (16)
C3	0.073 (2)	0.056 (2)	0.0618 (18)	−0.0078 (18)	0.0109 (16)	−0.0047 (15)
C4	0.065 (2)	0.057 (2)	0.0525 (17)	−0.0090 (18)	0.0092 (15)	−0.0024 (16)
C5	0.0578 (18)	0.0535 (19)	0.0489 (15)	−0.0051 (16)	0.0166 (14)	0.0034 (15)
C6	0.062 (2)	0.074 (2)	0.0617 (19)	−0.0002 (19)	0.0080 (16)	0.0071 (18)
C7	0.067 (2)	0.080 (3)	0.080 (2)	0.011 (2)	0.0131 (19)	0.010 (2)
C8	0.079 (2)	0.061 (2)	0.083 (2)	0.007 (2)	0.039 (2)	0.007 (2)
C9	0.062 (2)	0.059 (2)	0.0526 (17)	−0.0102 (18)	0.0249 (15)	−0.0031 (16)
C10	0.0535 (18)	0.0528 (19)	0.0455 (15)	−0.0091 (16)	0.0160 (13)	−0.0003 (14)
C11	0.068 (2)	0.069 (2)	0.0614 (18)	0.0025 (18)	0.0087 (16)	−0.0055 (18)
C12	0.071 (2)	0.116 (3)	0.068 (2)	0.001 (2)	−0.0050 (18)	−0.016 (2)
C13	0.087 (3)	0.118 (4)	0.069 (2)	−0.025 (3)	0.010 (2)	−0.037 (2)
C14	0.086 (3)	0.079 (3)	0.080 (2)	−0.014 (2)	0.034 (2)	−0.020 (2)

Geometric parameters (Å, º) top

N1—C4	1.279 (3)	C6—C7	1.383 (4)
N1—O1	1.407 (3)	C6—H6	0.9300
O1—C1	1.413 (3)	C7—C8	1.339 (4)
C1—C2	1.490 (4)	C7—H7	0.9300
C1—H1A	0.9700	C8—C9	1.412 (4)
C1—H1B	0.9700	C8—H8	0.9300
C2—C3	1.497 (4)	C9—C14	1.404 (4)
C2—H2A	0.9700	C9—C10	1.419 (4)
C2—H2B	0.9700	C10—C11	1.406 (4)
C3—C3ⁱ	1.513 (5)	C11—C12	1.354 (4)
C3—H3A	0.9700	C11—H11	0.9300
C3—H3B	0.9700	C12—C13	1.383 (5)
C4—C5	1.450 (4)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.340 (5)
C5—C6	1.364 (4)	C13—H13	0.9300
C5—C10	1.428 (4)	C14—H14	0.9300

C4—N1—O1	110.0 (2)	C5—C6—H6	118.3
N1—O1—C1	109.6 (2)	C7—C6—H6	118.3
O1—C1—C2	108.2 (2)	C8—C7—C6	119.4 (3)
O1—C1—H1A	110.1	C8—C7—H7	120.3
C2—C1—H1A	110.1	C6—C7—H7	120.3
O1—C1—H1B	110.1	C7—C8—C9	120.7 (3)
C2—C1—H1B	110.1	C7—C8—H8	119.7
H1A—C1—H1B	108.4	C9—C8—H8	119.7
C1—C2—C3	114.5 (2)	C14—C9—C8	121.1 (3)
C1—C2—H2A	108.6	C14—C9—C10	118.6 (3)
C3—C2—H2A	108.6	C8—C9—C10	120.2 (3)
C1—C2—H2B	108.6	C11—C10—C9	118.2 (3)
C3—C2—H2B	108.6	C11—C10—C5	124.1 (3)
H2A—C2—H2B	107.6	C9—C10—C5	117.7 (3)
C2—C3—C3ⁱ	114.2 (3)	C12—C11—C10	120.5 (3)
C2—C3—H3A	108.7	C12—C11—H11	119.8
C3ⁱ—C3—H3A	108.7	C10—C11—H11	119.8
C2—C3—H3B	108.7	C11—C12—C13	121.2 (3)
C3ⁱ—C3—H3B	108.7	C11—C12—H12	119.4
H3A—C3—H3B	107.6	C13—C12—H12	119.4
N1—C4—C5	125.4 (3)	C14—C13—C12	120.0 (3)
N1—C4—H4	117.3	C14—C13—H13	120.0
C5—C4—H4	117.3	C12—C13—H13	120.0
C6—C5—C10	118.5 (3)	C13—C14—C9	121.4 (3)
C6—C5—C4	116.1 (3)	C13—C14—H14	119.3
C10—C5—C4	125.3 (3)	C9—C14—H14	119.3
C5—C6—C7	123.4 (3)

C4—N1—O1—C1	−174.4 (2)	C8—C9—C10—C11	−178.2 (3)
N1—O1—C1—C2	−176.9 (2)	C14—C9—C10—C5	179.9 (2)
O1—C1—C2—C3	177.0 (2)	C8—C9—C10—C5	1.1 (4)
C1—C2—C3—C3ⁱ	−178.9 (3)	C6—C5—C10—C11	177.6 (3)
O1—N1—C4—C5	−176.7 (2)	C4—C5—C10—C11	−3.9 (4)
N1—C4—C5—C6	165.6 (3)	C6—C5—C10—C9	−1.7 (4)
N1—C4—C5—C10	−13.0 (4)	C4—C5—C10—C9	176.8 (2)
C10—C5—C6—C7	1.8 (4)	C9—C10—C11—C12	−0.3 (4)
C4—C5—C6—C7	−176.8 (3)	C5—C10—C11—C12	−179.6 (3)
C5—C6—C7—C8	−1.3 (5)	C10—C11—C12—C13	−0.4 (5)
C6—C7—C8—C9	0.6 (5)	C11—C12—C13—C14	1.0 (5)
C7—C8—C9—C14	−179.3 (3)	C12—C13—C14—C9	−0.8 (5)
C7—C8—C9—C10	−0.6 (4)	C8—C9—C14—C13	178.8 (3)
C14—C9—C10—C11	0.5 (4)	C10—C9—C14—C13	0.0 (5)

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₈N₂O₂
M_r	424.52
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.2925 (16), 6.3938 (12), 19.723 (2)
β (°)	96.489 (2)
V (Å³)	1164.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.47 × 0.42 × 0.23

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.965, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	5470, 2050, 1047
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.155, 1.08
No. of reflections	2050
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.12

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

Acknowledgements

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

References

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