6,6'-Dimeth-oxy-2,2'-[(hexane-1,6-diyldi-oxy)bis-(nitrilo-methyl-idyne)]diphenol.

In the title compound, C(22)H(28)N(2)O(6), strong intra-molecular O-H⋯N hydrogen bonds and weak inter-molecular C-H⋯O hydrogen bonds stabilize the three-dimensional supra-molecular structure.

Related literature

For related literature, see: Akine et al. (2005 ▶); Costes et al. (2000 ▶); Dong et al. (2006 ▶, 2007 ▶); Duan et al. (2007 ▶); Hoshino (1998 ▶); Jacobsen et al. (1991 ▶); Katsuki (1995 ▶); Lacroix (2001 ▶); Srinivasan et al. (1986 ▶); Zhang et al. (1990 ▶).

Experimental

Crystal data

C22H28N2O6

M = 416.46

Monoclinic,

a = 6.2913 (9) Å

b = 29.063 (3) Å

c = 12.0481 (15) Å

β = 100.063 (2)°

V = 2169.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.43 × 0.23 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.961, T max = 0.984

10858 measured reflections

3836 independent reflections

2138 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.130

S = 1.08

3836 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.14 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/S1600536808017789/hg2411sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017789/hg2411Isup2.hkl

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

C22H28N2O6	F000 = 888
Mr = 416.46	Dx = 1.275 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2277 reflections
a = 6.2913 (9) Å	θ = 2.2–22.7º
b = 29.063 (3) Å	µ = 0.09 mm−1
c = 12.0481 (15) Å	T = 298 (2) K
β = 100.063 (2)º	Prismatic, colorless
V = 2169.0 (5) Å3	0.43 × 0.23 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3836 independent reflections
Radiation source: fine-focus sealed tube	2138 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.042
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.961, Tmax = 0.984	k = −34→34
10858 measured reflections	l = −10→14

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.054P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
3836 reflections	Δρmax = 0.17 e Å−3
273 parameters	Δρmin = −0.14 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	1.1005 (3)	0.21438 (7)	0.56103 (16)	0.0423 (5)
N2	−0.1743 (4)	−0.00593 (7)	0.76432 (19)	0.0534 (6)
O1	0.9073 (3)	0.19166 (6)	0.52040 (13)	0.0500 (5)
O2	0.0109 (3)	0.02112 (6)	0.78379 (15)	0.0651 (6)
O3	1.4536 (3)	0.23525 (5)	0.70115 (13)	0.0471 (5)
H3	1.3377	0.2222	0.6810	0.071*
O4	1.8128 (3)	0.27994 (6)	0.74024 (14)	0.0536 (5)
O5	−0.5254 (3)	−0.04977 (6)	0.66091 (13)	0.0560 (5)
H5	−0.4150	−0.0344	0.6644	0.084*
O6	−0.8662 (3)	−0.09771 (6)	0.67802 (14)	0.0583 (5)
C1	0.8437 (4)	0.16557 (8)	0.6096 (2)	0.0460 (7)
H1A	0.8146	0.1861	0.6686	0.055*
H1B	0.9593	0.1449	0.6416	0.055*
C2	0.6460 (4)	0.13858 (9)	0.5642 (2)	0.0498 (7)
H2A	0.6793	0.1166	0.5092	0.060*
H2B	0.5355	0.1592	0.5263	0.060*
C3	0.5602 (4)	0.11318 (9)	0.6573 (2)	0.0500 (7)
H3A	0.6754	0.0944	0.6983	0.060*
H3B	0.5203	0.1356	0.7096	0.060*
C4	0.3675 (4)	0.08263 (9)	0.6171 (2)	0.0563 (7)
H4A	0.2565	0.1004	0.5698	0.068*
H4B	0.4104	0.0578	0.5718	0.068*
C5	0.2762 (4)	0.06249 (9)	0.7145 (2)	0.0511 (7)
H5A	0.3877	0.0444	0.7606	0.061*
H5B	0.2386	0.0875	0.7607	0.061*
C6	0.0802 (4)	0.03258 (9)	0.6804 (2)	0.0535 (7)
H6A	−0.0319	0.0491	0.6306	0.064*
H6B	0.1168	0.0051	0.6423	0.064*
C7	1.1556 (4)	0.24225 (8)	0.4897 (2)	0.0425 (6)
H7	1.0669	0.2460	0.4199	0.051*
C8	1.3543 (4)	0.26824 (7)	0.51555 (19)	0.0375 (6)
C9	1.4944 (4)	0.26352 (7)	0.61737 (19)	0.0364 (6)
C10	1.6878 (4)	0.28817 (8)	0.6385 (2)	0.0399 (6)
C11	1.7384 (4)	0.31800 (8)	0.5586 (2)	0.0508 (7)
H11	1.8668	0.3346	0.5722	0.061*
C12	1.5961 (5)	0.32325 (9)	0.4574 (2)	0.0577 (8)
H12	1.6297	0.3437	0.4036	0.069*
C13	1.4083 (5)	0.29895 (9)	0.4357 (2)	0.0520 (7)
H13	1.3153	0.3028	0.3674	0.062*
C14	2.0134 (4)	0.30314 (9)	0.7683 (2)	0.0622 (8)
H14A	2.0954	0.2989	0.7090	0.093*
H14B	2.0923	0.2908	0.8374	0.093*
H14C	1.9881	0.3354	0.7777	0.093*
C15	−0.2267 (4)	−0.01909 (8)	0.8565 (2)	0.0526 (7)
H15	−0.1392	−0.0103	0.9235	0.063*
C16	−0.4139 (4)	−0.04678 (8)	0.8628 (2)	0.0457 (7)
C17	−0.5556 (4)	−0.06051 (8)	0.7667 (2)	0.0410 (6)
C18	−0.7374 (4)	−0.08642 (8)	0.7769 (2)	0.0434 (6)
C19	−0.7739 (4)	−0.09855 (9)	0.8825 (2)	0.0518 (7)
H19	−0.8947	−0.1160	0.8894	0.062*
C20	−0.6334 (5)	−0.08513 (9)	0.9779 (2)	0.0602 (8)
H20	−0.6594	−0.0936	1.0488	0.072*
C21	−0.4562 (5)	−0.05942 (9)	0.9683 (2)	0.0570 (8)
H21	−0.3625	−0.0502	1.0329	0.068*
C22	−1.0452 (4)	−0.12698 (9)	0.6835 (2)	0.0630 (8)
H22A	−0.9947	−0.1555	0.7185	0.094*
H22B	−1.1217	−0.1328	0.6086	0.094*
H22C	−1.1402	−0.1123	0.7269	0.094*

	U11	U22	U33	U12	U13	U23
N1	0.0391 (13)	0.0454 (12)	0.0418 (12)	−0.0095 (10)	0.0050 (10)	−0.0060 (10)
N2	0.0475 (15)	0.0481 (13)	0.0663 (16)	−0.0098 (11)	0.0147 (12)	0.0014 (12)
O1	0.0465 (12)	0.0622 (11)	0.0398 (10)	−0.0191 (9)	0.0033 (8)	0.0022 (8)
O2	0.0556 (13)	0.0741 (13)	0.0667 (13)	−0.0256 (11)	0.0141 (10)	0.0043 (10)
O3	0.0448 (11)	0.0539 (10)	0.0411 (10)	−0.0083 (8)	0.0035 (8)	0.0085 (8)
O4	0.0394 (11)	0.0614 (11)	0.0544 (12)	−0.0089 (9)	−0.0073 (9)	0.0026 (9)
O5	0.0593 (13)	0.0662 (12)	0.0453 (11)	−0.0128 (10)	0.0167 (9)	0.0018 (9)
O6	0.0565 (13)	0.0676 (12)	0.0500 (12)	−0.0168 (10)	0.0070 (10)	0.0007 (9)
C1	0.0467 (17)	0.0468 (15)	0.0452 (16)	−0.0046 (13)	0.0100 (13)	0.0060 (13)
C2	0.0493 (17)	0.0531 (16)	0.0477 (16)	−0.0098 (14)	0.0100 (13)	0.0033 (13)
C3	0.0519 (18)	0.0507 (16)	0.0486 (16)	−0.0027 (14)	0.0124 (14)	0.0034 (13)
C4	0.0592 (19)	0.0590 (17)	0.0524 (17)	−0.0115 (15)	0.0144 (15)	0.0052 (14)
C5	0.0487 (18)	0.0516 (16)	0.0542 (17)	−0.0047 (14)	0.0122 (14)	0.0043 (13)
C6	0.0513 (18)	0.0515 (16)	0.0592 (18)	−0.0044 (14)	0.0136 (14)	0.0080 (14)
C7	0.0453 (17)	0.0452 (15)	0.0354 (14)	−0.0035 (13)	0.0023 (12)	−0.0006 (12)
C8	0.0431 (16)	0.0349 (13)	0.0346 (14)	−0.0037 (12)	0.0073 (12)	−0.0024 (11)
C9	0.0390 (16)	0.0345 (13)	0.0360 (14)	0.0005 (12)	0.0074 (12)	−0.0011 (11)
C10	0.0390 (16)	0.0387 (14)	0.0420 (15)	−0.0009 (12)	0.0067 (13)	−0.0046 (12)
C11	0.0482 (18)	0.0486 (16)	0.0565 (18)	−0.0137 (14)	0.0115 (15)	−0.0038 (14)
C12	0.071 (2)	0.0547 (17)	0.0498 (18)	−0.0166 (16)	0.0174 (16)	0.0079 (14)
C13	0.063 (2)	0.0549 (16)	0.0367 (15)	−0.0101 (15)	0.0058 (14)	0.0053 (13)
C14	0.0425 (18)	0.0679 (19)	0.072 (2)	−0.0089 (15)	−0.0016 (15)	−0.0131 (15)
C15	0.0488 (18)	0.0548 (17)	0.0531 (18)	−0.0098 (14)	0.0054 (14)	0.0035 (14)
C16	0.0481 (18)	0.0412 (15)	0.0489 (17)	−0.0027 (13)	0.0119 (14)	0.0012 (13)
C17	0.0466 (17)	0.0378 (14)	0.0417 (16)	0.0034 (13)	0.0164 (13)	0.0030 (12)
C18	0.0436 (17)	0.0427 (15)	0.0438 (16)	−0.0018 (13)	0.0073 (13)	−0.0020 (12)
C19	0.0516 (18)	0.0535 (16)	0.0526 (18)	−0.0097 (14)	0.0151 (15)	0.0024 (14)
C20	0.070 (2)	0.0666 (19)	0.0471 (18)	−0.0112 (17)	0.0197 (16)	0.0049 (15)
C21	0.064 (2)	0.0618 (18)	0.0434 (17)	−0.0077 (16)	0.0058 (15)	0.0012 (14)
C22	0.0527 (19)	0.0665 (18)	0.069 (2)	−0.0166 (16)	0.0082 (15)	−0.0045 (15)

N1—C7	1.273 (3)	C6—H6B	0.9700
N1—O1	1.395 (2)	C7—C8	1.447 (3)
N2—C15	1.271 (3)	C7—H7	0.9300
N2—O2	1.391 (3)	C8—C9	1.387 (3)
O1—C1	1.428 (3)	C8—C13	1.397 (3)
O2—C6	1.429 (3)	C9—C10	1.397 (3)
O3—C9	1.360 (3)	C10—C11	1.373 (3)
O3—H3	0.8200	C11—C12	1.390 (3)
O4—C10	1.357 (3)	C11—H11	0.9300
O4—C14	1.418 (3)	C12—C13	1.362 (3)
O5—C17	1.357 (3)	C12—H12	0.9300
O5—H5	0.8200	C13—H13	0.9300
O6—C18	1.359 (3)	C14—H14A	0.9600
O6—C22	1.422 (3)	C14—H14B	0.9600
C1—C2	1.491 (3)	C14—H14C	0.9600
C1—H1A	0.9700	C15—C16	1.439 (3)
C1—H1B	0.9700	C15—H15	0.9300
C2—C3	1.518 (3)	C16—C17	1.391 (3)
C2—H2A	0.9700	C16—C21	1.392 (3)
C2—H2B	0.9700	C17—C18	1.393 (3)
C3—C4	1.512 (3)	C18—C19	1.377 (3)
C3—H3A	0.9700	C19—C20	1.379 (4)
C3—H3B	0.9700	C19—H19	0.9300
C4—C5	1.511 (3)	C20—C21	1.364 (3)
C4—H4A	0.9700	C20—H20	0.9300
C4—H4B	0.9700	C21—H21	0.9300
C5—C6	1.506 (3)	C22—H22A	0.9600
C5—H5A	0.9700	C22—H22B	0.9600
C5—H5B	0.9700	C22—H22C	0.9600
C6—H6A	0.9700
C7—N1—O1	112.83 (19)	C13—C8—C7	119.3 (2)
C15—N2—O2	111.1 (2)	O3—C9—C8	122.9 (2)
N1—O1—C1	109.19 (17)	O3—C9—C10	116.5 (2)
N2—O2—C6	111.04 (19)	C8—C9—C10	120.6 (2)
C9—O3—H3	109.5	O4—C10—C11	125.1 (2)
C10—O4—C14	118.9 (2)	O4—C10—C9	115.0 (2)
C17—O5—H5	109.5	C11—C10—C9	119.8 (2)
C18—O6—C22	117.4 (2)	C10—C11—C12	119.5 (2)
O1—C1—C2	109.2 (2)	C10—C11—H11	120.3
O1—C1—H1A	109.8	C12—C11—H11	120.3
C2—C1—H1A	109.8	C13—C12—C11	121.0 (2)
O1—C1—H1B	109.8	C13—C12—H12	119.5
C2—C1—H1B	109.8	C11—C12—H12	119.5
H1A—C1—H1B	108.3	C12—C13—C8	120.4 (2)
C1—C2—C3	111.5 (2)	C12—C13—H13	119.8
C1—C2—H2A	109.3	C8—C13—H13	119.8
C3—C2—H2A	109.3	O4—C14—H14A	109.5
C1—C2—H2B	109.3	O4—C14—H14B	109.5
C3—C2—H2B	109.3	H14A—C14—H14B	109.5
H2A—C2—H2B	108.0	O4—C14—H14C	109.5
C4—C3—C2	114.7 (2)	H14A—C14—H14C	109.5
C4—C3—H3A	108.6	H14B—C14—H14C	109.5
C2—C3—H3A	108.6	N2—C15—C16	123.7 (3)
C4—C3—H3B	108.6	N2—C15—H15	118.2
C2—C3—H3B	108.6	C16—C15—H15	118.2
H3A—C3—H3B	107.6	C17—C16—C21	119.2 (2)
C5—C4—C3	111.8 (2)	C17—C16—C15	121.8 (2)
C5—C4—H4A	109.3	C21—C16—C15	119.0 (2)
C3—C4—H4A	109.3	O5—C17—C16	122.8 (2)
C5—C4—H4B	109.3	O5—C17—C18	117.4 (2)
C3—C4—H4B	109.3	C16—C17—C18	119.9 (2)
H4A—C4—H4B	107.9	O6—C18—C19	125.3 (2)
C6—C5—C4	114.6 (2)	O6—C18—C17	115.2 (2)
C6—C5—H5A	108.6	C19—C18—C17	119.5 (2)
C4—C5—H5A	108.6	C18—C19—C20	120.8 (3)
C6—C5—H5B	108.6	C18—C19—H19	119.6
C4—C5—H5B	108.6	C20—C19—H19	119.6
H5A—C5—H5B	107.6	C21—C20—C19	119.9 (3)
O2—C6—C5	104.9 (2)	C21—C20—H20	120.1
O2—C6—H6A	110.8	C19—C20—H20	120.1
C5—C6—H6A	110.8	C20—C21—C16	120.8 (3)
O2—C6—H6B	110.8	C20—C21—H21	119.6
C5—C6—H6B	110.8	C16—C21—H21	119.6
H6A—C6—H6B	108.8	O6—C22—H22A	109.5
N1—C7—C8	120.9 (2)	O6—C22—H22B	109.5
N1—C7—H7	119.5	H22A—C22—H22B	109.5
C8—C7—H7	119.5	O6—C22—H22C	109.5
C9—C8—C13	118.6 (2)	H22A—C22—H22C	109.5
C9—C8—C7	122.0 (2)	H22B—C22—H22C	109.5
C7—N1—O1—C1	−172.91 (19)	C10—C11—C12—C13	−0.6 (4)
C15—N2—O2—C6	175.0 (2)	C11—C12—C13—C8	0.3 (4)
N1—O1—C1—C2	−175.89 (18)	C9—C8—C13—C12	0.8 (4)
O1—C1—C2—C3	−175.30 (19)	C7—C8—C13—C12	−178.9 (2)
C1—C2—C3—C4	−176.4 (2)	O2—N2—C15—C16	178.7 (2)
C2—C3—C4—C5	−173.9 (2)	N2—C15—C16—C17	−1.4 (4)
C3—C4—C5—C6	178.6 (2)	N2—C15—C16—C21	179.8 (3)
N2—O2—C6—C5	178.64 (19)	C21—C16—C17—O5	−179.7 (2)
C4—C5—C6—O2	−174.7 (2)	C15—C16—C17—O5	1.5 (4)
O1—N1—C7—C8	−178.54 (19)	C21—C16—C17—C18	0.3 (4)
N1—C7—C8—C9	1.1 (4)	C15—C16—C17—C18	−178.5 (2)
N1—C7—C8—C13	−179.2 (2)	C22—O6—C18—C19	−4.5 (4)
C13—C8—C9—O3	178.6 (2)	C22—O6—C18—C17	175.5 (2)
C7—C8—C9—O3	−1.7 (4)	O5—C17—C18—O6	−0.6 (3)
C13—C8—C9—C10	−1.5 (3)	C16—C17—C18—O6	179.5 (2)
C7—C8—C9—C10	178.2 (2)	O5—C17—C18—C19	179.4 (2)
C14—O4—C10—C11	−0.6 (3)	C16—C17—C18—C19	−0.6 (4)
C14—O4—C10—C9	179.4 (2)	O6—C18—C19—C20	−179.7 (2)
O3—C9—C10—O4	1.1 (3)	C17—C18—C19—C20	0.4 (4)
C8—C9—C10—O4	−178.8 (2)	C18—C19—C20—C21	0.2 (4)
O3—C9—C10—C11	−178.9 (2)	C19—C20—C21—C16	−0.5 (4)
C8—C9—C10—C11	1.2 (3)	C17—C16—C21—C20	0.3 (4)
O4—C10—C11—C12	179.9 (2)	C15—C16—C21—C20	179.1 (2)
C9—C10—C11—C12	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2	0.82	1.95	2.662 (3)	145
O3—H3···N1	0.82	1.90	2.615 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯N2	0.82	1.95	2.662 (3)	145
O3—H3⋯N1	0.82	1.90	2.615 (3)	145