2,2′-[1,1′-(Decane-1,10-diyldioxy­dinitrilo)diethyl­idyne]diphenol

Wang, X.-Q.; Tong, J.-F.; Dong, W.-K.; Gong, S.-S.; Wu, J.-C.

doi:10.1107/S1600536809029341

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o2013

doi:10.1107/S1600536809029341

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2,2′-[1,1′-(Decane-1,10-diyldioxydinitrilo)diethylidyne]diphenol

Xiao-Qiang Wang,^a Jun-Feng Tong,^a Wen-Kui Dong,^a ^* Shang-Sheng Gong ^a and Jian-Chao Wu ^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 8 July 2009; accepted 23 July 2009; online 29 July 2009)

The salen-type bis-oxime title compound, C₂₆H₃₆N₂O₄, lies about a crystallographic inversion centre. Classical intramolecular O—H⋯N hydrogen bonds generate two S(6) ring motifs. In the crystal structure, pairs of weak intermolecular C—H⋯O hydrogen bonds link adjacent molecules into an infinite one-dimensional supramolecular structure.

Related literature

For the strong coordination capability and diverse biological activity of Schiff bases, see: Boskovic et al. (2003 ); Koizumi et al. (2005 ); Oshiob et al. (2005 ). For the use of Schiff base derivatives to develop protein and enzyme mimics, see: Santos et al. (2001 ). For our studies of synthesis and structure of salen-type bisoxime compounds obtained by Schiff base reactions, see: Dong et al. (2008a ,b , 2009 ). For hydrogen bonds, see: Desiraju (1996 ).

Experimental

Crystal data

C₂₆H₃₆N₂O₄
M_r = 440.57
Monoclinic, C 2/c
a = 13.0031 (16) Å
b = 4.6922 (6) Å
c = 40.654 (3) Å
β = 93.109 (2)°
V = 2476.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.50 × 0.48 × 0.23 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.962, T_max = 0.982
5830 measured reflections
2124 independent reflections
1209 reflections with I > 2σ(I)
R_int = 0.076

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.260
S = 1.03
2124 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.23 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	1.85	2.568 (5)	146
C13—H13⋯O2ⁱ	0.93	2.66	3.565 (6)	163
Symmetry code: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

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/S1600536809029341/ds2001sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029341/ds2001Isup2.hkl

checkCIF report

Comment top

Schiff bases are one of most prevalent mixed-donor ligands in the field of coordination chemistry and have been intensively studied due to their strong coordination capability as well as their diverse biological activities, such as antibacterial, antitumor, etc. (Koizumi et al., 2005; Boskovic et al., 2003; Oshiob et al., 2005). In addition, many Schiff base derivatives have been synthesized and employed to develop protein and enzyme mimics (Santos et al., 2001). Our group is interested in the synthesis and structure of salen-type bisoxime compounds by Schiff base reaction (Dong et al., 2008a; Dong et al., 2008b). Here, we report, for the first time, the synthesis and crystal structure of a salen-type bisoxime compound containing ten-methene bridge, 2,2'-[1,1'-(decane-1,10-diyldioxydinitrilo)diethylidyne]diphenol.

Perspective view of the title molecule, showing the atomic numbering scheme, is given in Fig. 1. Each molecule exists in a trans configuration with respect to the methylidene unit. The two phenyl rings in each molecule are parallel to each other, with C1—O1—N1—C7 torsion angles of 178.7 (3)° and a perpendicular interplanar spacing of ca 6.695 (2) Å. In each title compound, there exist two classical intramolecular O—H···N hydrogen bonds (Fig. 1) which generate two six-membered rings, producing two S(6) ring motifs. In the crystal structure, pairs of weak intermolecular C—H···O hydrogen bonds (Table 1, Fig. 2)(Desiraju, 1996) link the adjacent molecules into an infinite one-dimensional supramolecular structure (Fig. 2).

Related literature top

For the strong coordination capability and diverse biological activities of Schiff bases, see: Boskovic et al. (2003); Koizumi et al. (2005); Oshiob et al. (2005). For the use of Schiff base derivatives to develop protein and enzyme mimics, see: Santos et al. (2001). For our studies of synthesis and structure of salen-type bisoxime compounds obtained by Schiff base reaction, see: Dong et al. (2008a,b, 2009). For hydrogen bonds, see: Desiraju (1996).

Experimental top

2,2'-[1,1'-(Decane-1,10-diyldioxydinitrilo)diethylidyne]diphenol was synthesized according to the literature (Dong, et al., 2009). To an absolute ethanol solution (4 ml) of 2'-hydroxyacetophenone (375.8 mg, 2.76 mmol) was added an absolute ethanol solution (4 ml) of 1, 10-bis(aminooxy)decane (180.9 mg, 1.38 mmol). The mixture solution was stirred at 328–333 K for 48 h. When cool to room temperature (298 K), white precipitate was formed which was filtered and washed successively with absolute ethanol (2 ml) and n-hexane (8 ml), respectively. The product was dried under vacuum and purified by recrystallization from ethanol to yield 331.9 mg of the title compound. Yield, 52.75%. m. p. 343–344 K. Anal. Calcd. for C₂₆H₃₆N₂O₄: C, 70.88; H, 8.24; N, 6.36. Found: C, 70.59; H, 8.23; N, 6.57.

Colorless block-like single crystals suitable for X-ray diffraction studies were obtained after several days by slow evaporation from a diethyl ether solution of the title compound.

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

2,2'-[1,1'-(Decane-1,10-diyldioxydinitrilo)diethylidyne]diphenol top

Crystal data top

C₂₆H₃₆N₂O₄	F(000) = 952
M_r = 440.57	D_x = 1.181 Mg m⁻³
Monoclinic, C2/c	Melting point = 343–344 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 13.0031 (16) Å	Cell parameters from 1361 reflections
b = 4.6922 (6) Å	θ = 2.5–26.9°
c = 40.654 (3) Å	µ = 0.08 mm⁻¹
β = 93.109 (2)°	T = 298 K
V = 2476.8 (5) Å³	Block-like, colorless
Z = 4	0.50 × 0.48 × 0.23 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2124 independent reflections
Radiation source: fine-focus sealed tube	1209 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.076
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.962, T_max = 0.982	k = −5→5
5830 measured reflections	l = −44→48

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.260	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.1008P)² + 5.3906P] where P = (F_o² + 2F_c²)/3
2124 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₆H₃₆N₂O₄	V = 2476.8 (5) Å³
M_r = 440.57	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 13.0031 (16) Å	µ = 0.08 mm⁻¹
b = 4.6922 (6) Å	T = 298 K
c = 40.654 (3) Å	0.50 × 0.48 × 0.23 mm
β = 93.109 (2)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2124 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1209 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.982	R_int = 0.076
5830 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.260	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
2124 reflections	Δρ_min = −0.23 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
O1	0.6948 (2)	0.6651 (8)	0.60162 (7)	0.0693 (9)
O2	0.5126 (2)	0.3324 (9)	0.66379 (8)	0.0803 (11)
H2	0.5375	0.4228	0.6489	0.120*
N1	0.6559 (2)	0.5081 (8)	0.62776 (8)	0.0544 (9)
C1	0.6125 (3)	0.8304 (11)	0.58630 (10)	0.0620 (12)
H1A	0.6413	0.9723	0.5721	0.074*
H1B	0.5769	0.9302	0.6032	0.074*
C2	0.5353 (3)	0.6509 (11)	0.56611 (10)	0.0573 (11)
H2A	0.5718	0.5358	0.5507	0.069*
H2B	0.5010	0.5226	0.5807	0.069*
C3	0.4551 (3)	0.8281 (11)	0.54718 (10)	0.0584 (11)
H3A	0.4895	0.9470	0.5316	0.070*
H3B	0.4227	0.9536	0.5625	0.070*
C4	0.3718 (3)	0.6584 (11)	0.52849 (10)	0.0596 (11)
H4A	0.3377	0.5384	0.5440	0.071*
H4B	0.4040	0.5342	0.5130	0.071*
C5	0.2911 (3)	0.8377 (11)	0.50978 (10)	0.0639 (12)
H5A	0.3253	0.9613	0.4947	0.077*
H5B	0.2574	0.9581	0.5253	0.077*
C6	0.8336 (3)	0.3275 (14)	0.63241 (13)	0.0859 (17)
H6A	0.8384	0.1795	0.6163	0.129*
H6B	0.8786	0.2842	0.6513	0.129*
H6C	0.8535	0.5060	0.6231	0.129*
C7	0.7246 (3)	0.3474 (10)	0.64272 (9)	0.0508 (10)
C8	0.6903 (3)	0.1753 (10)	0.67002 (9)	0.0510 (10)
C9	0.5870 (3)	0.1717 (11)	0.67948 (11)	0.0626 (12)
C10	0.5576 (4)	0.0034 (13)	0.70503 (12)	0.0759 (14)
H10	0.4895	0.0057	0.7109	0.091*
C11	0.6286 (4)	−0.1700 (13)	0.72215 (12)	0.0785 (15)
H11	0.6078	−0.2850	0.7392	0.094*
C12	0.7295 (4)	−0.1711 (12)	0.71384 (12)	0.0778 (15)
H12	0.7773	−0.2859	0.7254	0.093*
C13	0.7603 (3)	−0.0015 (11)	0.68828 (10)	0.0639 (12)
H13	0.8290	−0.0041	0.6830	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0520 (16)	0.081 (2)	0.0734 (19)	−0.0094 (18)	−0.0129 (14)	0.0220 (19)
O2	0.0520 (17)	0.085 (2)	0.104 (2)	0.0082 (19)	0.0014 (16)	0.027 (2)
N1	0.0458 (17)	0.058 (2)	0.0580 (19)	−0.0004 (19)	−0.0087 (15)	0.0059 (19)
C1	0.057 (2)	0.064 (3)	0.064 (2)	−0.010 (3)	−0.016 (2)	0.019 (2)
C2	0.051 (2)	0.061 (3)	0.058 (2)	0.004 (2)	−0.0098 (18)	0.009 (2)
C3	0.055 (2)	0.060 (3)	0.060 (2)	−0.003 (2)	−0.0069 (19)	0.017 (2)
C4	0.053 (2)	0.062 (3)	0.063 (2)	−0.001 (3)	−0.0090 (19)	0.012 (2)
C5	0.054 (2)	0.071 (3)	0.066 (3)	0.003 (3)	−0.011 (2)	0.016 (3)
C6	0.056 (3)	0.100 (4)	0.102 (4)	0.008 (3)	0.001 (3)	0.029 (4)
C7	0.045 (2)	0.050 (2)	0.056 (2)	0.002 (2)	−0.0076 (18)	−0.007 (2)
C8	0.051 (2)	0.046 (2)	0.055 (2)	0.012 (2)	−0.0067 (18)	−0.007 (2)
C9	0.062 (3)	0.056 (3)	0.069 (3)	0.005 (3)	0.000 (2)	−0.002 (3)
C10	0.074 (3)	0.075 (3)	0.079 (3)	0.003 (3)	0.010 (3)	0.003 (3)
C11	0.102 (4)	0.066 (3)	0.067 (3)	−0.003 (4)	0.008 (3)	0.006 (3)
C12	0.101 (4)	0.065 (3)	0.066 (3)	0.024 (3)	−0.010 (3)	−0.002 (3)
C13	0.066 (3)	0.062 (3)	0.062 (3)	0.013 (3)	−0.007 (2)	−0.005 (3)

Geometric parameters (Å, º) top

O1—N1	1.409 (4)	C5—H5A	0.9700
O1—C1	1.436 (5)	C5—H5B	0.9700
O2—C9	1.359 (5)	C6—C7	1.502 (6)
O2—H2	0.8200	C6—H6A	0.9600
N1—C7	1.296 (5)	C6—H6B	0.9600
C1—C2	1.517 (6)	C6—H6C	0.9600
C1—H1A	0.9700	C7—C8	1.462 (6)
C1—H1B	0.9700	C8—C13	1.413 (5)
C2—C3	1.511 (5)	C8—C9	1.417 (6)
C2—H2A	0.9700	C9—C10	1.376 (7)
C2—H2B	0.9700	C10—C11	1.389 (7)
C3—C4	1.515 (6)	C10—H10	0.9300
C3—H3A	0.9700	C11—C12	1.373 (7)
C3—H3B	0.9700	C11—H11	0.9300
C4—C5	1.516 (5)	C12—C13	1.385 (7)
C4—H4A	0.9700	C12—H12	0.9300
C4—H4B	0.9700	C13—H13	0.9300
C5—C5ⁱ	1.537 (8)

N1—O1—C1	108.7 (3)	C4—C5—H5B	108.8
C9—O2—H2	109.5	C5ⁱ—C5—H5B	108.8
C7—N1—O1	113.1 (3)	H5A—C5—H5B	107.7
O1—C1—C2	113.0 (4)	C7—C6—H6A	109.5
O1—C1—H1A	109.0	C7—C6—H6B	109.5
C2—C1—H1A	109.0	H6A—C6—H6B	109.5
O1—C1—H1B	109.0	C7—C6—H6C	109.5
C2—C1—H1B	109.0	H6A—C6—H6C	109.5
H1A—C1—H1B	107.8	H6B—C6—H6C	109.5
C3—C2—C1	112.8 (4)	N1—C7—C8	116.5 (3)
C3—C2—H2A	109.0	N1—C7—C6	122.8 (4)
C1—C2—H2A	109.0	C8—C7—C6	120.6 (4)
C3—C2—H2B	109.0	C13—C8—C9	116.4 (4)
C1—C2—H2B	109.0	C13—C8—C7	120.6 (4)
H2A—C2—H2B	107.8	C9—C8—C7	123.1 (4)
C2—C3—C4	114.9 (4)	O2—C9—C10	116.9 (4)
C2—C3—H3A	108.5	O2—C9—C8	121.9 (4)
C4—C3—H3A	108.5	C10—C9—C8	121.2 (4)
C2—C3—H3B	108.5	C9—C10—C11	120.7 (5)
C4—C3—H3B	108.5	C9—C10—H10	119.7
H3A—C3—H3B	107.5	C11—C10—H10	119.7
C3—C4—C5	114.6 (4)	C12—C11—C10	119.8 (5)
C3—C4—H4A	108.6	C12—C11—H11	120.1
C5—C4—H4A	108.6	C10—C11—H11	120.1
C3—C4—H4B	108.6	C11—C12—C13	120.1 (5)
C5—C4—H4B	108.6	C11—C12—H12	119.9
H4A—C4—H4B	107.6	C13—C12—H12	119.9
C4—C5—C5ⁱ	113.9 (5)	C12—C13—C8	121.8 (4)
C4—C5—H5A	108.8	C12—C13—H13	119.1
C5ⁱ—C5—H5A	108.8	C8—C13—H13	119.1

C1—O1—N1—C7	178.7 (3)	C13—C8—C9—O2	−180.0 (4)
N1—O1—C1—C2	−72.6 (4)	C7—C8—C9—O2	−0.7 (7)
O1—C1—C2—C3	−174.0 (4)	C13—C8—C9—C10	−0.2 (7)
C1—C2—C3—C4	−175.9 (4)	C7—C8—C9—C10	179.0 (4)
C2—C3—C4—C5	179.5 (4)	O2—C9—C10—C11	179.3 (5)
C3—C4—C5—C5ⁱ	178.5 (5)	C8—C9—C10—C11	−0.5 (8)
O1—N1—C7—C8	−179.5 (3)	C9—C10—C11—C12	0.9 (8)
O1—N1—C7—C6	−1.4 (6)	C10—C11—C12—C13	−0.5 (8)
N1—C7—C8—C13	−178.6 (4)	C11—C12—C13—C8	−0.2 (8)
C6—C7—C8—C13	3.3 (6)	C9—C8—C13—C12	0.6 (6)
N1—C7—C8—C9	2.2 (6)	C7—C8—C13—C12	−178.7 (4)
C6—C7—C8—C9	−175.9 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.85	2.568 (5)	146
C13—H13···O2ⁱⁱ	0.93	2.66	3.565 (6)	163

Symmetry code: (ii) x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₃₆N₂O₄
M_r	440.57
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	13.0031 (16), 4.6922 (6), 40.654 (3)
β (°)	93.109 (2)
V (Å³)	2476.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.48 × 0.23

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.962, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	5830, 2124, 1209
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.260, 1.03
No. of reflections	2124
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.23

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	1.85	2.568 (5)	145.9
C13—H13···O2ⁱ	0.93	2.66	3.565 (6)	163.4

Symmetry code: (i) x+1/2, y−1/2, z.

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (No. 0904-11) and the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University, which are gratefully acknowledged.

References

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