6,6'-Dieth-oxy-2,2'-[hexane-1,6-diylbis(nitrilo-methanylyl-idene)]diphenol.

The title compound, C(24)H(32)N(2)O(4), is a polydentate Schiff base and reveals strong intra-molecular O-H⋯N hydrogen bonding between the hy-droxy O atom and the imino N atom, with an O⋯N distance of 2.570 (3) Å. In the crystal, a centre of inversion is located at the mid-point of the compound. The diimino-hexyl-ene chain is almost ideally in the anti conformation, with an average dihedral angle of 179.0°.

Related literature

For related structures, see: Bermejo et al. (2007 ▶); Fun et al. (2009 ▶); Ha (2010 ▶).

Experimental

Crystal data

C24H32N2O4

M = 412.52

Triclinic,

a = 6.9094 (13) Å

b = 6.9184 (13) Å

c = 11.936 (2) Å

α = 91.271 (5)°

β = 99.677 (4)°

γ = 102.550 (4)°

V = 547.97 (18) Å3

Z = 1

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.26 × 0.23 × 0.23 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.862, T max = 1.000

3505 measured reflections

2140 independent reflections

1258 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.168

S = 1.02

2140 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009445/ds2098sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009445/ds2098Isup2.hkl

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

C24H32N2O4	Z = 1
Mr = 412.52	F(000) = 222
Triclinic, P1	Dx = 1.250 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9094 (13) Å	Cell parameters from 873 reflections
b = 6.9184 (13) Å	θ = 3.1–25.7°
c = 11.936 (2) Å	µ = 0.09 mm−1
α = 91.271 (5)°	T = 200 K
β = 99.677 (4)°	Stick, yellow
γ = 102.550 (4)°	0.26 × 0.23 × 0.23 mm
V = 547.97 (18) Å3

Bruker SMART 1000 CCD diffractometer	2140 independent reflections
Radiation source: fine-focus sealed tube	1258 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 26.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.862, Tmax = 1.000	k = −8→8
3505 measured reflections	l = −14→11

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0725P)2 + 0.0011P] where P = (Fo2 + 2Fc2)/3
2140 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.21 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	0.5421 (2)	0.2477 (3)	0.24546 (17)	0.0424 (5)
H1	0.5714	0.3570	0.2834	0.064*
O2	0.5003 (2)	−0.0878 (2)	0.13057 (16)	0.0405 (5)
N1	0.7714 (3)	0.5589 (3)	0.35709 (19)	0.0383 (6)
C1	0.9039 (3)	0.3153 (3)	0.2687 (2)	0.0312 (6)
C2	0.7131 (3)	0.1965 (3)	0.2277 (2)	0.0318 (6)
C3	0.6946 (4)	0.0168 (4)	0.1652 (2)	0.0327 (6)
C4	0.8654 (4)	−0.0394 (4)	0.1439 (2)	0.0367 (7)
H4	0.8526	−0.1599	0.1007	0.044*
C5	1.0562 (4)	0.0782 (4)	0.1849 (2)	0.0399 (7)
H5	1.1729	0.0374	0.1705	0.048*
C6	1.0750 (4)	0.2543 (4)	0.2467 (2)	0.0357 (7)
H6	1.2051	0.3348	0.2745	0.043*
C7	0.4707 (4)	−0.2781 (3)	0.0726 (2)	0.0400 (7)
H7A	0.5449	−0.3639	0.1196	0.048*
H7B	0.5193	−0.2641	−0.0009	0.048*
C8	0.2475 (4)	−0.3664 (4)	0.0530 (3)	0.0492 (8)
H8A	0.2003	−0.3725	0.1261	0.074*
H8B	0.2202	−0.5005	0.0170	0.074*
H8C	0.1767	−0.2835	0.0032	0.074*
C9	0.9234 (4)	0.5017 (4)	0.3333 (2)	0.0351 (6)
H9	1.0540	0.5831	0.3585	0.042*
C10	0.7949 (4)	0.7477 (4)	0.4222 (2)	0.0394 (7)
H10A	0.8727	0.8568	0.3846	0.047*
H10B	0.8707	0.7421	0.4998	0.047*
C11	0.5920 (4)	0.7884 (3)	0.4300 (2)	0.0384 (7)
H11A	0.5143	0.6766	0.4657	0.046*
H11B	0.5179	0.7939	0.3520	0.046*
C12	0.6021 (3)	0.9794 (4)	0.4974 (2)	0.0366 (7)
H12A	0.6735	0.9729	0.5760	0.044*
H12B	0.6819	1.0911	0.4626	0.044*

	U11	U22	U33	U12	U13	U23
O1	0.0309 (10)	0.0439 (11)	0.0537 (13)	0.0112 (8)	0.0094 (9)	−0.0110 (9)
O2	0.0304 (10)	0.0369 (10)	0.0523 (13)	0.0049 (7)	0.0070 (9)	−0.0091 (9)
N1	0.0373 (12)	0.0389 (13)	0.0416 (14)	0.0150 (10)	0.0080 (11)	−0.0040 (11)
C1	0.0289 (13)	0.0342 (14)	0.0323 (15)	0.0099 (10)	0.0068 (12)	0.0001 (12)
C2	0.0278 (13)	0.0360 (14)	0.0356 (16)	0.0128 (11)	0.0096 (12)	0.0012 (12)
C3	0.0330 (14)	0.0323 (14)	0.0331 (15)	0.0076 (11)	0.0061 (12)	0.0017 (12)
C4	0.0387 (14)	0.0367 (14)	0.0372 (16)	0.0129 (11)	0.0087 (13)	−0.0053 (12)
C5	0.0318 (14)	0.0461 (16)	0.0465 (18)	0.0148 (12)	0.0127 (13)	−0.0029 (14)
C6	0.0282 (13)	0.0389 (15)	0.0401 (16)	0.0075 (11)	0.0066 (12)	−0.0007 (12)
C7	0.0397 (15)	0.0322 (15)	0.0469 (18)	0.0078 (11)	0.0052 (13)	−0.0025 (13)
C8	0.0450 (16)	0.0375 (16)	0.060 (2)	−0.0003 (12)	0.0075 (15)	−0.0070 (14)
C9	0.0305 (13)	0.0347 (14)	0.0387 (16)	0.0049 (11)	0.0056 (12)	−0.0011 (12)
C10	0.0410 (15)	0.0387 (15)	0.0385 (17)	0.0123 (12)	0.0037 (13)	−0.0083 (13)
C11	0.0401 (15)	0.0351 (15)	0.0429 (17)	0.0121 (11)	0.0112 (13)	−0.0035 (13)
C12	0.0381 (15)	0.0336 (15)	0.0387 (16)	0.0107 (11)	0.0056 (13)	−0.0032 (12)

O1—C2	1.353 (3)	C7—C8	1.506 (4)
O1—H1	0.8400	C7—H7A	0.9900
O2—C3	1.369 (3)	C7—H7B	0.9900
O2—C7	1.431 (3)	C8—H8A	0.9800
N1—C9	1.271 (3)	C8—H8B	0.9800
N1—C10	1.469 (3)	C8—H8C	0.9800
C1—C2	1.396 (3)	C9—H9	0.9500
C1—C6	1.401 (3)	C10—C11	1.506 (3)
C1—C9	1.456 (3)	C10—H10A	0.9900
C2—C3	1.406 (3)	C10—H10B	0.9900
C3—C4	1.379 (3)	C11—C12	1.514 (3)
C4—C5	1.393 (3)	C11—H11A	0.9900
C4—H4	0.9500	C11—H11B	0.9900
C5—C6	1.380 (3)	C12—C12i	1.510 (4)
C5—H5	0.9500	C12—H12A	0.9900
C6—H6	0.9500	C12—H12B	0.9900
C2—O1—H1	109.5	C7—C8—H8A	109.5
C3—O2—C7	117.46 (18)	C7—C8—H8B	109.5
C9—N1—C10	121.2 (2)	H8A—C8—H8B	109.5
C2—C1—C6	119.5 (2)	C7—C8—H8C	109.5
C2—C1—C9	119.9 (2)	H8A—C8—H8C	109.5
C6—C1—C9	120.6 (2)	H8B—C8—H8C	109.5
O1—C2—C1	122.4 (2)	N1—C9—C1	122.2 (2)
O1—C2—C3	117.9 (2)	N1—C9—H9	118.9
C1—C2—C3	119.8 (2)	C1—C9—H9	118.9
O2—C3—C4	126.0 (2)	N1—C10—C11	110.5 (2)
O2—C3—C2	114.4 (2)	N1—C10—H10A	109.6
C4—C3—C2	119.6 (2)	C11—C10—H10A	109.6
C3—C4—C5	120.9 (2)	N1—C10—H10B	109.6
C3—C4—H4	119.6	C11—C10—H10B	109.6
C5—C4—H4	119.6	H10A—C10—H10B	108.1
C6—C5—C4	119.7 (2)	C10—C11—C12	114.0 (2)
C6—C5—H5	120.2	C10—C11—H11A	108.7
C4—C5—H5	120.2	C12—C11—H11A	108.7
C5—C6—C1	120.6 (2)	C10—C11—H11B	108.7
C5—C6—H6	119.7	C12—C11—H11B	108.7
C1—C6—H6	119.7	H11A—C11—H11B	107.6
O2—C7—C8	106.4 (2)	C12i—C12—C11	113.5 (3)
O2—C7—H7A	110.4	C12i—C12—H12A	108.9
C8—C7—H7A	110.4	C11—C12—H12A	108.9
O2—C7—H7B	110.4	C12i—C12—H12B	108.9
C8—C7—H7B	110.4	C11—C12—H12B	108.9
H7A—C7—H7B	108.6	H12A—C12—H12B	107.7
C6—C1—C2—O1	−179.6 (2)	C3—C4—C5—C6	−0.7 (4)
C9—C1—C2—O1	0.1 (4)	C4—C5—C6—C1	0.2 (4)
C6—C1—C2—C3	0.2 (4)	C2—C1—C6—C5	0.0 (4)
C9—C1—C2—C3	179.9 (2)	C9—C1—C6—C5	−179.6 (3)
C7—O2—C3—C4	3.8 (4)	C3—O2—C7—C8	175.5 (2)
C7—O2—C3—C2	−176.2 (2)	C10—N1—C9—C1	−179.9 (3)
O1—C2—C3—O2	−0.9 (4)	C2—C1—C9—N1	2.1 (4)
C1—C2—C3—O2	179.3 (2)	C6—C1—C9—N1	−178.3 (3)
O1—C2—C3—C4	179.1 (2)	C9—N1—C10—C11	175.2 (3)
C1—C2—C3—C4	−0.7 (4)	N1—C10—C11—C12	179.1 (2)
O2—C3—C4—C5	−179.1 (2)	C10—C11—C12—C12i	178.8 (3)
C2—C3—C4—C5	0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.83	2.570 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84	1.83	2.570 (3)	147