6,6′-Dimeth­oxy-2,2′-[(hexane-1,6-diyldi­oxy)bis­(nitrilo­methyl­idyne)]diphenol

Dong, W.-K.; Zhao, C.-Y.; Zhong, J.-K.; Tang, X.-L.; Yu, T.-Z.

doi:10.1107/S1600536808017789

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1323

doi:10.1107/S1600536808017789

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6,6′-Dimethoxy-2,2′-[(hexane-1,6-diyldioxy)bis(nitrilomethylidyne)]diphenol

Wen-Kui Dong,^a ^* Chun-Yu Zhao,^a Jin-Kui Zhong,^a Xiao-Lu Tang ^a and Tian-Zhi Yu ^b

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China, and ^bKey Laboratory of Opto-Electronic Technology and Intelligent Control, Lanzhou Jiaotong University, Ministry of Education, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: dongwk@mail.lzjtu.cn

(Received 2 June 2008; accepted 12 June 2008; online 21 June 2008)

In the title compound, C₂₂H₂₈N₂O₆, strong intramolecular O—H⋯N hydrogen bonds and weak intermolecular C—H⋯O hydrogen bonds stabilize the three-dimensional supramolecular 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_r = 416.46
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.130
S = 1.08
3836 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.14 e Å⁻³

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

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017789/hg2411sup1.cif

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

checkCIF report

Comment top

Salen-type compound and its derivatives have attracted much attention to many organic as well as inorganic chemists, because these compounds can easily form complexes with various transition metal ions (Jacobsen et al.;1991, Katsuki et al.,1995). Some of them or their metal complexes are used as a catalyst in various organic reactions (Srinivasan et al., 1986; Zhang et al., 1990), nonlinear optical materials (Lacroix et al., 2001), and metallomesogens (Hoshino et al.,1998) or exhibit interesting magnetic properties (Costes et al., 2000) and so forth. To develop stable analogues of salen-type ligands, we synthesized a new class of salen-type bisoxime compounds on the basis of O-alkyl oxime moiety (–CH=N—O-(CH₂)_n-O—N=CH–) instead of the imine moiety (Dong et al., 2006; Duan et al., 2007). The larger electronegativity of oxygen atoms is expected to affect strongly the electronic properties of N₂O₂ coordination sphere, which can lead to different and novel properties and structures of the resulted complexes (Akine et al.,2005). Thus modification of a basic salen skeleton is very interesting and important. In this paper, a novel bisoxime ligand, 6,6'-dimethoxy-2,2'-[(hexane-1,6-diyldioxy)bis(nitrilomethylidyne)]diphenol (I) has been synthesized by 2 equiv. of 3-methoxysalicylidene and 1 equiv. of 1,6-bis(aminooxy)hexane, and shown in Fig. 1.

X-ray crystallographic analysis reveals the crystal structure of the bisoxime ligand (I), Which consists of discrete C₂₂H₂₈N₂O₆ molecules in which all bond lengths are in normal ranges. The dihedral angle of the two benzene rings is 20.9 (2)°. The oxime groups have anti-conformation, and there are strong O3—H3···N1 and O5—H5···N2 intramolecular hydrogen bonds and weak C7—H7···O3 and C22—H22A···C10 intermolecular hydrogen bonds, stabilize the three-dimensional supramolecuar structure of (I).

Related literature top

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 top

The title compound (I) was synthesized according to an analogous method reported earlier (Dong et al., 2007). To an ethanol solution (5 ml) of 3-methoxysalicylidene (265.6 mg, 1.75 mmol) was added an ethanol (3 ml) solution of 1,6-bis(aminooxy)hexane (129.4 mg, 0.87 mmol). After the solution had been stirred at 328 K for 4 h, the mixture was filtered. The residue was washed successively with ethanol and ethanol/hexane (1:4), respectively. The product was dried under vacuum to yield 60.62 mg of (I). Yield, 16.7%. mp. 382–384 K. Anal. Calc. for C₂₂H₂₈N₂O₆: C, 63.45; H, 6.78; N, 6.73. Found: C, 63.47; H, 6.79; N, 6.61%.

Colorless prismatic single crystals suitable for X-ray diffraction studies were obtained after several weeks by slow evaporation from a mixture of ethanol/acetone (1:3) of (I) at room temperture.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecule structure of (I) with atom numbering. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.

6,6'-Dimethoxy-2,2'-[(hexane-1,6-diyldioxy)bis(nitrilomethylidyne)]diphenol top

Crystal data top

C₂₂H₂₈N₂O₆	F(000) = 888
M_r = 416.46	D_x = 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 = 2.2–22.7°
b = 29.063 (3) Å	µ = 0.09 mm⁻¹
c = 12.0481 (15) Å	T = 298 K
β = 100.063 (2)°	Prismatic, colorless
V = 2169.0 (5) Å³	0.43 × 0.23 × 0.17 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3836 independent reflections
Radiation source: fine-focus sealed tube	2138 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.961, T_max = 0.984	k = −34→34
10858 measured reflections	l = −10→14

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.054P)²] where P = (F_o² + 2F_c²)/3
3836 reflections	(Δ/σ)_max < 0.001
273 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₂H₂₈N₂O₆	V = 2169.0 (5) Å³
M_r = 416.46	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.2913 (9) Å	µ = 0.09 mm⁻¹
b = 29.063 (3) Å	T = 298 K
c = 12.0481 (15) Å	0.43 × 0.23 × 0.17 mm
β = 100.063 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3836 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2138 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.984	R_int = 0.042
10858 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.08	Δρ_max = 0.17 e Å⁻³
3836 reflections	Δρ_min = −0.14 e Å⁻³
273 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₈N₂O₆
M_r	416.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	6.2913 (9), 29.063 (3), 12.0481 (15)
β (°)	100.063 (2)
V (Å³)	2169.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.43 × 0.23 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.961, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	10858, 3836, 2138
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.130, 1.08
No. of reflections	3836
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.14

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2	0.82	1.95	2.662 (3)	145.4
O3—H3···N1	0.82	1.90	2.615 (3)	145.0

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (No. 0604-01) and the `Qing Lan' Talent Engineering Funds of Lanzhou Jiaotong University (No. QL-03-01 A), which are gratefully acknowledged.

References

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Volume 64| Part 7| July 2008| Page o1323

doi:10.1107/S1600536808017789

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

6,6′-Dimeth­­oxy-2,2′-[(hexane-1,6-diyldi­­oxy)bis­­(nitrilo­methyl­­idyne)]diphenol

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6,6′-Dimethoxy-2,2′-[(hexane-1,6-diyldioxy)bis(nitrilomethylidyne)]diphenol