2,2'-[1,1'-(Decane-1,10-diyldioxy-dinitrilo)diethyl-idyne]diphenol.

The salen-type bis-oxime title compound, C(26)H(36)N(2)O(4), lies about a crystallographic inversion centre. Classical intra-molecular O-H⋯N hydrogen bonds generate two S(6) ring motifs. In the crystal structure, pairs of weak inter-molecular C-H⋯O hydrogen bonds link adjacent mol-ecules into an infinite one-dimensional supra-molecular 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 = 440.57

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.260

S = 1.03

2124 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.23 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029341/ds2001sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H36N2O4	F(000) = 952
Mr = 440.57	Dx = 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

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

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(Fo2) + (0.1008P)2 + 5.3906P] where P = (Fo2 + 2Fc2)/3
2124 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .