2,2'-[1,1'-(Hexane-1,6-diyldioxy-dinitrilo)diethyl-idyne]diphenol.

The molecule of the title compound, C(22)H(28)N(2)O(2), lies across an inversion centre with one half-mol-ecule in the asymmetric unit. The mol-ecule adopts an E configuration with respect to the azomethine C=N bond and the imino group is coplanar with the aromatic ring. Within the mol-ecule, the planar units are parallel, but extend in opposite directions from the hexa-methyl-ene bridge. There are intra-molecular O-H⋯N hydrogen bonds between the hydroxyl groups and the oxime N atoms. There are also weak inter-molecular C-H⋯O bonds that link each mol-ecule to two others, forming chains along the a axis.

Related literature

For related literature, see: Atwood (1997 ▶); Canali & Sherrington (1999 ▶); Dong et al. (2007 ▶, 2008a ▶,b ▶,c ▶); Jarrahpour et al. (2004 ▶); Sun et al. (2004 ▶); Venkataramanan et al. (2005 ▶); Wang et al. (2007 ▶); Yu et al. (2008 ▶).

Experimental

Crystal data

C22H28N2O4

M = 384.46

Monoclinic,

a = 13.0052 (19) Å

b = 4.6441 (6) Å

c = 34.221 (3) Å

β = 95.000 (2)°

V = 2059.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.50 × 0.43 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.959, T max = 0.982

4854 measured reflections

1816 independent reflections

1025 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.185

S = 1.06

1816 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SMART; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024902/fl2214sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024902/fl2214Isup2.hkl

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

C22H28N2O4	F000 = 824
Mr = 384.46	Dx = 1.240 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C -2yc	Cell parameters from 1018 reflections
a = 13.0052 (19) Å	θ = 2.4–23.2º
b = 4.6441 (6) Å	µ = 0.09 mm−1
c = 34.221 (3) Å	T = 298 (2) K
β = 95.000 (2)º	Block-shaped, colorless
V = 2059.0 (4) Å3	0.50 × 0.43 × 0.22 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1816 independent reflections
Radiation source: fine-focus sealed tube	1025 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.081
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −12→15
Tmin = 0.959, Tmax = 0.982	k = −5→5
4854 measured reflections	l = −36→40

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)] = 0.066	H-atom parameters constrained
wR(F2) = 0.185	w = 1/[σ2(Fo2) + (0.0707P)2 + 0.7764P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1816 reflections	Δρmax = 0.16 e Å−3
127 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.20750 (18)	0.7620 (6)	0.39536 (6)	0.0558 (7)
O1	0.25649 (15)	0.9218 (5)	0.42661 (6)	0.0689 (7)
O2	0.04940 (15)	0.5889 (6)	0.35249 (6)	0.0814 (8)
H2	0.0805	0.6818	0.3702	0.122*
C1	0.1805 (2)	1.0874 (8)	0.44434 (8)	0.0634 (9)
H1A	0.1380	1.1879	0.4240	0.076*
H1B	0.2149	1.2310	0.4614	0.076*
C2	0.1115 (2)	0.9044 (7)	0.46802 (8)	0.0568 (8)
H2A	0.0712	0.7748	0.4505	0.068*
H2B	0.1541	0.7885	0.4866	0.068*
C3	0.0392 (2)	1.0874 (7)	0.49000 (7)	0.0545 (8)
H3A	0.0796	1.2005	0.5096	0.065*
H3B	0.0030	1.2202	0.4717	0.065*
C4	0.3827 (2)	0.5826 (10)	0.38989 (9)	0.0837 (12)
H4A	0.4084	0.7690	0.3980	0.126*
H4B	0.4184	0.5160	0.3682	0.126*
H4C	0.3938	0.4498	0.4113	0.126*
C5	0.2690 (2)	0.6031 (7)	0.37758 (8)	0.0501 (7)
C6	0.2230 (2)	0.4313 (7)	0.34493 (7)	0.0496 (7)
C7	0.1174 (2)	0.4300 (8)	0.33391 (8)	0.0606 (8)
C8	0.0770 (3)	0.2574 (9)	0.30335 (9)	0.0776 (10)
H8	0.0062	0.2574	0.2965	0.093*
C9	0.1397 (3)	0.0870 (9)	0.28307 (9)	0.0786 (11)
H9	0.1116	−0.0283	0.2626	0.094*
C10	0.2445 (3)	0.0870 (8)	0.29310 (9)	0.0751 (10)
H10	0.2876	−0.0278	0.2794	0.090*
C11	0.2846 (2)	0.2562 (8)	0.32321 (8)	0.0626 (9)
H11	0.3556	0.2553	0.3296	0.075*

	U11	U22	U33	U12	U13	U23
N1	0.0568 (14)	0.0595 (17)	0.0530 (13)	−0.0017 (15)	0.0155 (11)	−0.0068 (13)
O1	0.0583 (12)	0.0827 (17)	0.0685 (12)	−0.0034 (13)	0.0215 (10)	−0.0199 (12)
O2	0.0554 (13)	0.093 (2)	0.0976 (16)	0.0061 (14)	0.0143 (12)	−0.0252 (15)
C1	0.0693 (19)	0.059 (2)	0.0651 (17)	−0.0062 (18)	0.0267 (15)	−0.0163 (16)
C2	0.0571 (17)	0.056 (2)	0.0589 (16)	0.0034 (17)	0.0163 (13)	−0.0037 (16)
C3	0.0593 (17)	0.0524 (19)	0.0535 (16)	0.0009 (16)	0.0144 (13)	−0.0038 (15)
C4	0.0543 (19)	0.108 (3)	0.089 (2)	0.011 (2)	0.0101 (16)	−0.027 (2)
C5	0.0506 (16)	0.0483 (18)	0.0542 (15)	0.0036 (15)	0.0202 (13)	0.0017 (15)
C6	0.0562 (17)	0.0486 (18)	0.0464 (14)	0.0036 (16)	0.0172 (12)	0.0078 (14)
C7	0.0634 (19)	0.059 (2)	0.0610 (18)	0.0055 (18)	0.0157 (15)	0.0015 (17)
C8	0.077 (2)	0.079 (3)	0.077 (2)	−0.004 (2)	0.0061 (18)	−0.007 (2)
C9	0.108 (3)	0.070 (3)	0.0583 (19)	−0.003 (2)	0.008 (2)	−0.0042 (18)
C10	0.107 (3)	0.064 (2)	0.0571 (19)	0.019 (2)	0.0239 (18)	−0.0010 (18)
C11	0.074 (2)	0.061 (2)	0.0547 (17)	0.012 (2)	0.0190 (15)	0.0036 (17)

N1—C5	1.281 (3)	C4—H4A	0.9600
N1—O1	1.408 (3)	C4—H4B	0.9600
O1—C1	1.429 (3)	C4—H4C	0.9600
O2—C7	1.352 (4)	C5—C6	1.458 (4)
O2—H2	0.8200	C6—C7	1.393 (4)
C1—C2	1.520 (4)	C6—C11	1.399 (4)
C1—H1A	0.9700	C7—C8	1.384 (5)
C1—H1B	0.9700	C8—C9	1.368 (5)
C2—C3	1.515 (4)	C8—H8	0.9300
C2—H2A	0.9700	C9—C10	1.376 (5)
C2—H2B	0.9700	C9—H9	0.9300
C3—C3i	1.512 (5)	C10—C11	1.363 (5)
C3—H3A	0.9700	C10—H10	0.9300
C3—H3B	0.9700	C11—H11	0.9300
C4—C5	1.504 (4)
C5—N1—O1	113.9 (2)	C5—C4—H4C	109.5
N1—O1—C1	108.8 (2)	H4A—C4—H4C	109.5
C7—O2—H2	109.5	H4B—C4—H4C	109.5
O1—C1—C2	112.8 (3)	N1—C5—C6	116.6 (2)
O1—C1—H1A	109.0	N1—C5—C4	122.9 (3)
C2—C1—H1A	109.0	C6—C5—C4	120.5 (3)
O1—C1—H1B	109.0	C7—C6—C11	116.8 (3)
C2—C1—H1B	109.0	C7—C6—C5	122.6 (3)
H1A—C1—H1B	107.8	C11—C6—C5	120.6 (3)
C3—C2—C1	111.8 (2)	O2—C7—C8	116.8 (3)
C3—C2—H2A	109.3	O2—C7—C6	122.7 (3)
C1—C2—H2A	109.3	C8—C7—C6	120.5 (3)
C3—C2—H2B	109.3	C9—C8—C7	120.9 (3)
C1—C2—H2B	109.3	C9—C8—H8	119.5
H2A—C2—H2B	107.9	C7—C8—H8	119.5
C3i—C3—C2	113.3 (3)	C8—C9—C10	119.6 (3)
C3i—C3—H3A	108.9	C8—C9—H9	120.2
C2—C3—H3A	108.9	C10—C9—H9	120.2
C3i—C3—H3B	108.9	C11—C10—C9	119.6 (3)
C2—C3—H3B	108.9	C11—C10—H10	120.2
H3A—C3—H3B	107.7	C9—C10—H10	120.2
C5—C4—H4A	109.5	C10—C11—C6	122.5 (3)
C5—C4—H4B	109.5	C10—C11—H11	118.8
H4A—C4—H4B	109.5	C6—C11—H11	118.8
C5—N1—O1—C1	−179.4 (2)	C5—C6—C7—O2	0.3 (5)
N1—O1—C1—C2	72.4 (3)	C11—C6—C7—C8	1.3 (5)
O1—C1—C2—C3	173.9 (2)	C5—C6—C7—C8	−178.3 (3)
C1—C2—C3—C3i	173.2 (3)	O2—C7—C8—C9	−179.4 (3)
O1—N1—C5—C6	179.9 (2)	C6—C7—C8—C9	−0.7 (5)
O1—N1—C5—C4	1.9 (4)	C7—C8—C9—C10	−0.1 (5)
N1—C5—C6—C7	−1.9 (4)	C8—C9—C10—C11	0.2 (5)
C4—C5—C6—C7	176.1 (3)	C9—C10—C11—C6	0.5 (5)
N1—C5—C6—C11	178.5 (3)	C7—C6—C11—C10	−1.2 (4)
C4—C5—C6—C11	−3.4 (4)	C5—C6—C11—C10	178.4 (3)
C11—C6—C7—O2	179.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.83	2.549 (3)	145
C4—H4B···O2ii	0.96	2.70	3.476 (4)	138
C11—H11···O2ii	0.93	2.69	3.587 (4)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.83	2.549 (3)	145
C4—H4B⋯O2i	0.96	2.70	3.476 (4)	138
C11—H11⋯O2i	0.93	2.69	3.587 (4)	163

Symmetry code: (i) .