2,2'-[1,1'-(Octane-1,8-diyldioxy-dinitrilo)diethyl-idyne]diphenol.

The title compound, C(24)H(32)N(2)O(4), has a crystallographic inversion centre at the mid-point of the central C-C bond. At each end of the mol-ecule, intra-molecular O-H⋯N hydrogen bonds generate six-membered S(6) ring motifs. The crystal structure is stabilized by pairs of weak inter-molecular C-H⋯O hydrogen bonds that link neighbouring mol-ecules into R(2) (2)(40) ring motifs, which in turn form infinite one-dimensional supra-molecular ribbon structures.

Related literature

For background to oxime-based salen-type tetra­dentate ligands, see: Akine et al. (2005 ▶); Dong, He et al. (2009 ▶); Dong, Sun et al. (2009 ▶). For the synthesis, see: Dong et al. (2008 ▶). For related structures, see: Dong, Zhao et al. (2009 ▶); Etemadi et al. (2009 ▶). For information relating to C—H⋯O hydrogen bonds, see: Desiraju (1996 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C24H32N2O4

M = 412.52

Monoclinic,

a = 12.9524 (12) Å

b = 4.6667 (6) Å

c = 37.722 (3) Å

β = 99.379 (2)°

V = 2249.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.50 × 0.48 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.960, T max = 0.984

5371 measured reflections

1979 independent reflections

1172 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.173

S = 1.11

1979 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 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 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033959/pk2184sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033959/pk2184Isup2.hkl

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

C24H32N2O4	F(000) = 888
Mr = 412.52	Dx = 1.218 Mg m−3
Monoclinic, C2/c	Melting point = 345–347 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 12.9524 (12) Å	Cell parameters from 1491 reflections
b = 4.6667 (6) Å	θ = 2.2–27.2°
c = 37.722 (3) Å	µ = 0.08 mm−1
β = 99.379 (2)°	T = 298 K
V = 2249.6 (4) Å3	Block-like, colorless
Z = 4	0.50 × 0.48 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	1979 independent reflections
Radiation source: fine-focus sealed tube	1172 reflections with I > 2σ(I)
graphite	Rint = 0.069
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→15
Tmin = 0.960, Tmax = 0.984	k = −5→5
5371 measured reflections	l = −37→44

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.074	H-atom parameters constrained
wR(F2) = 0.173	w = 1/[σ2(Fo2) + (0.0225P)2 + 4.9486P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
1979 reflections	Δρmax = 0.20 e Å−3
137 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0080 (9)

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
N1	0.3869 (2)	0.5102 (7)	0.38238 (7)	0.0490 (8)
O1	0.35769 (17)	0.6700 (6)	0.41082 (6)	0.0617 (8)
O2	0.51778 (18)	0.3352 (7)	0.34323 (7)	0.0746 (9)
H2	0.4980	0.4288	0.3593	0.112*
C1	0.4459 (3)	0.8346 (9)	0.42728 (9)	0.0570 (10)
H1A	0.4224	0.9786	0.4427	0.068*
H1B	0.4757	0.9335	0.4087	0.068*
C2	0.5297 (2)	0.6538 (9)	0.44922 (9)	0.0513 (9)
H2A	0.5594	0.5254	0.4333	0.062*
H2B	0.4983	0.5377	0.4659	0.062*
C3	0.6162 (2)	0.8345 (9)	0.46995 (9)	0.0518 (9)
H3A	0.5870	0.9513	0.4872	0.062*
H3B	0.6430	0.9627	0.4534	0.062*
C4	0.7063 (2)	0.6595 (9)	0.48983 (9)	0.0540 (10)
H4A	0.6796	0.5333	0.5067	0.065*
H4B	0.7347	0.5406	0.4727	0.065*
C5	0.3132 (2)	0.3491 (8)	0.36639 (8)	0.0440 (9)
C6	0.2085 (3)	0.3295 (12)	0.37779 (11)	0.0786 (14)
H6A	0.1970	0.1371	0.3852	0.118*
H6B	0.1552	0.3805	0.3580	0.118*
H6C	0.2059	0.4585	0.3975	0.118*
C7	0.3382 (2)	0.1742 (8)	0.33664 (8)	0.0447 (9)
C8	0.4372 (3)	0.1723 (9)	0.32643 (10)	0.0547 (10)
C9	0.4582 (3)	0.0008 (10)	0.29864 (11)	0.0699 (12)
H9	0.5247	0.0013	0.2924	0.084*
C10	0.3815 (4)	−0.1708 (10)	0.28013 (10)	0.0714 (12)
H10	0.3961	−0.2862	0.2615	0.086*
C11	0.2835 (4)	−0.1710 (10)	0.28930 (10)	0.0699 (12)
H11	0.2313	−0.2859	0.2767	0.084*
C12	0.2619 (3)	−0.0026 (9)	0.31692 (9)	0.0587 (11)
H12	0.1948	−0.0054	0.3228	0.070*

	U11	U22	U33	U12	U13	U23
N1	0.0372 (16)	0.058 (2)	0.0459 (16)	0.0005 (15)	−0.0117 (12)	−0.0031 (17)
O1	0.0381 (14)	0.081 (2)	0.0591 (15)	0.0022 (14)	−0.0132 (11)	−0.0207 (16)
O2	0.0399 (14)	0.092 (2)	0.0886 (19)	−0.0111 (16)	0.0020 (13)	−0.0267 (19)
C1	0.044 (2)	0.061 (2)	0.057 (2)	0.001 (2)	−0.0190 (16)	−0.017 (2)
C2	0.0416 (19)	0.060 (2)	0.0460 (19)	−0.0056 (19)	−0.0126 (15)	−0.001 (2)
C3	0.0413 (19)	0.060 (2)	0.0483 (19)	−0.002 (2)	−0.0097 (15)	−0.012 (2)
C4	0.0395 (19)	0.061 (2)	0.056 (2)	−0.004 (2)	−0.0099 (15)	−0.009 (2)
C5	0.0320 (18)	0.050 (2)	0.0437 (18)	−0.0007 (17)	−0.0128 (14)	0.0062 (19)
C6	0.045 (2)	0.108 (4)	0.080 (3)	−0.017 (3)	0.0029 (19)	−0.024 (3)
C7	0.0380 (19)	0.046 (2)	0.0433 (18)	−0.0042 (17)	−0.0124 (14)	0.0072 (18)
C8	0.050 (2)	0.054 (2)	0.055 (2)	−0.001 (2)	−0.0078 (17)	−0.003 (2)
C9	0.061 (3)	0.080 (3)	0.067 (3)	0.002 (3)	0.005 (2)	−0.003 (3)
C10	0.092 (3)	0.068 (3)	0.051 (2)	0.005 (3)	0.001 (2)	−0.002 (2)
C11	0.083 (3)	0.066 (3)	0.051 (2)	−0.019 (3)	−0.016 (2)	0.003 (2)
C12	0.055 (2)	0.064 (3)	0.051 (2)	−0.012 (2)	−0.0112 (17)	0.009 (2)

N1—C5	1.285 (4)	C4—H4B	0.9700
N1—O1	1.408 (3)	C5—C7	1.466 (5)
O1—C1	1.432 (4)	C5—C6	1.491 (5)
O2—C8	1.361 (4)	C6—H6A	0.9600
O2—H2	0.8200	C6—H6B	0.9600
C1—C2	1.511 (5)	C6—H6C	0.9600
C1—H1A	0.9700	C7—C8	1.398 (5)
C1—H1B	0.9700	C7—C12	1.404 (5)
C2—C3	1.514 (5)	C8—C9	1.380 (5)
C2—H2A	0.9700	C9—C10	1.375 (6)
C2—H2B	0.9700	C9—H9	0.9300
C3—C4	1.518 (5)	C10—C11	1.369 (5)
C3—H3A	0.9700	C10—H10	0.9300
C3—H3B	0.9700	C11—C12	1.370 (5)
C4—C4i	1.517 (6)	C11—H11	0.9300
C4—H4A	0.9700	C12—H12	0.9300
C5—N1—O1	113.3 (3)	N1—C5—C7	116.5 (3)
N1—O1—C1	108.7 (3)	N1—C5—C6	122.8 (3)
C8—O2—H2	109.5	C7—C5—C6	120.7 (3)
O1—C1—C2	112.9 (3)	C5—C6—H6A	109.5
O1—C1—H1A	109.0	C5—C6—H6B	109.5
C2—C1—H1A	109.0	H6A—C6—H6B	109.5
O1—C1—H1B	109.0	C5—C6—H6C	109.5
C2—C1—H1B	109.0	H6A—C6—H6C	109.5
H1A—C1—H1B	107.8	H6B—C6—H6C	109.5
C1—C2—C3	112.1 (3)	C8—C7—C12	116.7 (3)
C1—C2—H2A	109.2	C8—C7—C5	122.7 (3)
C3—C2—H2A	109.2	C12—C7—C5	120.6 (3)
C1—C2—H2B	109.2	O2—C8—C9	116.5 (4)
C3—C2—H2B	109.2	O2—C8—C7	122.4 (3)
H2A—C2—H2B	107.9	C9—C8—C7	121.0 (4)
C2—C3—C4	113.6 (3)	C10—C9—C8	120.5 (4)
C2—C3—H3A	108.8	C10—C9—H9	119.7
C4—C3—H3A	108.8	C8—C9—H9	119.7
C2—C3—H3B	108.8	C11—C10—C9	119.7 (4)
C4—C3—H3B	108.8	C11—C10—H10	120.2
H3A—C3—H3B	107.7	C9—C10—H10	120.2
C4i—C4—C3	113.6 (4)	C10—C11—C12	120.3 (4)
C4i—C4—H4A	108.8	C10—C11—H11	119.9
C3—C4—H4A	108.8	C12—C11—H11	119.9
C4i—C4—H4B	108.8	C11—C12—C7	121.8 (4)
C3—C4—H4B	108.8	C11—C12—H12	119.1
H4A—C4—H4B	107.7	C7—C12—H12	119.1
C5—N1—O1—C1	178.4 (3)	C12—C7—C8—O2	179.6 (3)
N1—O1—C1—C2	−72.6 (4)	C5—C7—C8—O2	−0.6 (6)
O1—C1—C2—C3	−173.2 (3)	C12—C7—C8—C9	−1.0 (5)
C1—C2—C3—C4	−175.1 (3)	C5—C7—C8—C9	178.8 (3)
C2—C3—C4—C4i	179.2 (4)	O2—C8—C9—C10	−180.0 (4)
O1—N1—C5—C7	−179.5 (3)	C7—C8—C9—C10	0.6 (6)
O1—N1—C5—C6	−1.6 (5)	C8—C9—C10—C11	0.1 (6)
N1—C5—C7—C8	2.0 (5)	C9—C10—C11—C12	−0.4 (6)
C6—C5—C7—C8	−176.0 (4)	C10—C11—C12—C7	0.0 (6)
N1—C5—C7—C12	−178.2 (3)	C8—C7—C12—C11	0.7 (5)
C6—C5—C7—C12	3.8 (5)	C5—C7—C12—C11	−179.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.84	2.558 (4)	145
C12—H12···O2ii	0.93	2.64	3.544 (5)	164

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	2.558 (4)	145
C12—H12⋯O2i	0.93	2.64	3.544 (5)	164

Symmetry code: (i) .