5,5′-Dimeth­oxy-2,2′-[(pentane-1,5-diyl­dioxy)bis­(nitrilo­methyl­idyne)]diphenol

Sun, Y.-X.; Li, L.; Dong, W.-K.; Wu, J.-C.; Tong, J.-F.

doi:10.1107/S1600536809014986

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1160

doi:10.1107/S1600536809014986

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5,5′-Dimethoxy-2,2′-[(pentane-1,5-diyldioxy)bis(nitrilomethylidyne)]diphenol

Yin-Xia Sun,^a Li Li,^a Wen-Kui Dong,^a ^* Jian-Chao Wu ^a and Jun-Feng Tong ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: dongwk@mail.lzjtu.cn

(Received 17 April 2009; accepted 22 April 2009; online 30 April 2009)

The molecule of the title compound, C₂₁H₂₆N₂O₆, which lies across a crystallographic inversion centre, crystallizes with two unique half-molecules in the symmetric unit and adopts a linear configuration and the imino group is coplanar with the aromatic ring, making a dihedral angle of 3.26 (3)°. Strong intramolecular O—H⋯N and weak intermolecular O—H⋯O and C—H⋯O hydrogen bonds and weak intermolecular π–π stacking interactions [centroid–centroid distance = 4.419 (2) Å]establish an infinite three-dimensional supramolecular structure.

Related literature

For the properties and uses of salen-type compounds, see: Lacroix (2001 ); Nishijo et al. (2006 ); Onda et al. (2007 ); Sun et al. (2004 ). For the structures of free salen-type compounds, see: Akine et al. (2005 ). For related structures, see: Dong et al. (2008a ,b , 2009 ).

Experimental

Crystal data

C₂₁H₂₆N₂O₆
M_r = 402.44
Triclinic, $[P \overline 1]$
a = 7.3324 (15) Å
b = 7.6214 (17) Å
c = 20.372 (3) Å
α = 81.525 (1)°
β = 89.928 (2)°
γ = 67.870 (1)°
V = 1041.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.43 × 0.28 × 0.14 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.961, T_max = 0.987
5481 measured reflections
3618 independent reflections
1641 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.124
S = 1.01
3618 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1	0.82	1.90	2.610 (3)	144
O5—H5⋯N2	0.82	1.90	2.628 (3)	147
O3—H3⋯O3ⁱ	0.82	2.68	3.045 (3)	109
C2—H2A⋯O3ⁱⁱ	0.97	2.58	3.533 (4)	168
C19—H19⋯O5ⁱⁱ	0.93	2.44	3.300 (4)	154
Symmetry codes: (i) -x-1, -y+2, -z; (ii) x+1, y, z.

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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014986/hg2502sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014986/hg2502Isup2.hkl

checkCIF report

Comment top

Salen-type compound and its derivatives are among the most prevalent mixed-donor ligands in the field of modern coordination chemistry in which there has been growing interest, mainly because of their interesting and important properties, including optical features (Lacroix, 2001), catalytic activity in hydration of acrylonitrile (Onda et al., 2007) and magnetic properties (Nishijo et al., 2006). They can also be used as elemental building blocks for construction of supramolecular structures via intermolecular hydrogen bonding or short contact interaction (Sun et al., 2004). Many salen-type complexes have been structurally characterized, but only a relatively small number of free salen-type compounds have had their X-ray structures reported (Akine et al., 2005). In order to extent our work (Dong et al., 2008a) on structural characterization of salen-type bisoxime compounds, we reported the synthesis and structure of the title compound in this paper in Fig. 1.

The molecule of the title salen-type bisoxime compound lies across a crystallographic inversion centre and adopts a linear configuration with respect to the azomethine C=N bonds. The dihedral angle formed by the two benzene rings is 23.4 (2) °, and the imino group is coplanar with the aromatic ring. This structure is different from our previous work reported in which the molecules assume W-shaped configuration (Dong et al., 2008a) or E configuration (Dong et al., 2008b).

There are two strong intramolecular O—H···N hydrogen bonds involving the hydroxy group and oxime N atoms in each molecule. In the crystal structure, intermolecular C—H···O and O—H···O hydrogen bonds link the each molecule to three others, and weak intermolecular π-π stacking interaction between the neighbouring benzene rings (the inter-molecular plane-to-plane dihedral angle along b axis is 0.48 (4) °). Thus, an infinite three-dimensional supramolecular structure is established (Fig. 2).

Related literature top

For the properties and uses of salen-type compounds, see: Lacroix (2001); Nishijo et al. (2006); Onda et al. (2007); Sun et al. (2004). For the structures of free salen-type compounds, see: Akine et al. (2005). For related sturctures, see: Dong et al. (2008a,b, 2009).

Experimental top

5,5'-Dimethoxy-2,2'-[(pentane-1,5-diyldioxy)bis(nitrilomethylidyne)]diphenol was synthesized according to an analogous method reported earlier (Dong et al., 2009). To an ethanol solution (10 ml) of 4-methoxy-2-hydroxybenzaldehyde (304.3 mg, 2.00 mmol) was added an ethanol solution (6 ml) of 1,5-bis(aminooxy)pentane (134.2 mg, 1.00 mmol). The reaction mixture was stirred at 328 K for 5 h. The formed precipitate was separated by filtration, and washed successively with ethanol and ethanol-hexane (1:4), respectively. The product was dried under vacuum to yield 204.2 mg of the title compound. Yield, 51.8%. mp. 349–350 K. Anal. Calc. for C₂₁H₂₆N₂O₆: C, 62.67; H, 6.51; N, 9.96. Found: C, 62.79; H, 6.68; N, 6.83.

Colorless block-like single crystals suitable for X-ray diffraction studies were obtained after about two months by slow evaporation from an ethanol solution of the title compound.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (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 molecular structure of the title compound with atom numbering scheme [Symmetry codes: #1 - x + 1,-y + 1,-z + 1]. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
	Fig. 2. Part of the supramolecular structure of the title compound. Intra- and intermolecular hydrogen bonds are shown as dashed lines.

5,5'-Dimethoxy-2,2'-[(pentane-1,5-diyldioxy)bis(nitrilomethylidyne)]diphenol top

Crystal data top

C₂₁H₂₆N₂O₆	Z = 2
M_r = 402.44	F(000) = 428
Triclinic, P1	D_x = 1.284 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3324 (15) Å	Cell parameters from 974 reflections
b = 7.6214 (17) Å	θ = 2.9–23.1°
c = 20.372 (3) Å	µ = 0.09 mm⁻¹
α = 81.525 (1)°	T = 298 K
β = 89.928 (2)°	Block-like, colorless
γ = 67.870 (1)°	0.43 × 0.28 × 0.14 mm
V = 1041.2 (3) Å³

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3618 independent reflections
Radiation source: fine-focus sealed tube	1641 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.961, T_max = 0.987	k = −9→8
5481 measured reflections	l = −24→15

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0371P)²] where P = (F_o² + 2F_c²)/3
3618 reflections	(Δ/σ)_max < 0.001
264 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₁H₂₆N₂O₆	γ = 67.870 (1)°
M_r = 402.44	V = 1041.2 (3) Å³
Triclinic, P1	Z = 2
a = 7.3324 (15) Å	Mo Kα radiation
b = 7.6214 (17) Å	µ = 0.09 mm⁻¹
c = 20.372 (3) Å	T = 298 K
α = 81.525 (1)°	0.43 × 0.28 × 0.14 mm
β = 89.928 (2)°

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	3618 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1641 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.987	R_int = 0.028
5481 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.01	Δρ_max = 0.15 e Å⁻³
3618 reflections	Δρ_min = −0.18 e Å⁻³
264 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	−0.1725 (3)	0.8216 (3)	−0.07342 (10)	0.0615 (6)
N2	0.8214 (3)	0.4398 (3)	0.28534 (10)	0.0657 (6)
O1	0.0265 (3)	0.7497 (3)	−0.05195 (8)	0.0749 (6)
O2	0.7701 (3)	0.4917 (3)	0.21730 (8)	0.0800 (6)
O3	−0.5543 (2)	0.9488 (3)	−0.06470 (8)	0.0882 (7)
H3	−0.4405	0.9249	−0.0516	0.132*
O4	−0.9588 (3)	1.0916 (3)	−0.25645 (9)	0.0917 (7)
O5	0.8015 (2)	0.3232 (3)	0.41215 (8)	0.0891 (7)
H5	0.7610	0.3633	0.3732	0.134*
O6	1.3399 (3)	0.2041 (3)	0.55807 (9)	0.0906 (7)
C1	0.0438 (4)	0.7272 (4)	0.01908 (12)	0.0678 (8)
H1A	−0.0151	0.6387	0.0387	0.081*
H1B	−0.0235	0.8497	0.0339	0.081*
C2	0.2584 (4)	0.6508 (4)	0.03966 (11)	0.0699 (8)
H2A	0.3156	0.7376	0.0173	0.084*
H2B	0.3220	0.5279	0.0248	0.084*
C3	0.3029 (4)	0.6250 (4)	0.11341 (11)	0.0651 (8)
H3A	0.2570	0.5291	0.1357	0.078*
H3B	0.2305	0.7449	0.1292	0.078*
C4	0.5200 (4)	0.5643 (4)	0.13208 (12)	0.0662 (8)
H4A	0.5930	0.4465	0.1151	0.079*
H4B	0.5651	0.6621	0.1109	0.079*
C5	0.5645 (4)	0.5332 (4)	0.20517 (12)	0.0692 (8)
H5A	0.4861	0.6473	0.2233	0.083*
H5B	0.5322	0.4272	0.2266	0.083*
C6	−0.1984 (4)	0.8436 (4)	−0.13669 (12)	0.0607 (7)
H6	−0.0899	0.8147	−0.1628	0.073*
C7	−0.3954 (4)	0.9133 (4)	−0.16794 (12)	0.0528 (7)
C8	−0.5646 (4)	0.9604 (4)	−0.13165 (12)	0.0599 (8)
C9	−0.7468 (4)	1.0168 (4)	−0.16277 (13)	0.0729 (9)
H9	−0.8574	1.0445	−0.1377	0.087*
C10	−0.7693 (4)	1.0334 (4)	−0.23081 (14)	0.0633 (8)
C11	−0.6068 (4)	0.9916 (4)	−0.26870 (13)	0.0691 (8)
H11	−0.6201	1.0020	−0.3147	0.083*
C12	−0.4233 (4)	0.9337 (4)	−0.23622 (12)	0.0661 (8)
H12	−0.3132	0.9071	−0.2615	0.079*
C13	−0.9911 (4)	1.1077 (4)	−0.32617 (14)	0.0919 (11)
H13A	−0.9339	1.1923	−0.3489	0.138*
H13B	−1.1303	1.1582	−0.3376	0.138*
H13C	−0.9310	0.9834	−0.3392	0.138*
C14	0.9944 (4)	0.4320 (4)	0.29886 (13)	0.0642 (8)
H14	1.0649	0.4660	0.2647	0.077*
C15	1.0837 (4)	0.3722 (4)	0.36552 (12)	0.0534 (7)
C16	0.9873 (4)	0.3203 (4)	0.42012 (13)	0.0611 (8)
C17	1.0779 (4)	0.2636 (4)	0.48276 (13)	0.0727 (9)
H17	1.0124	0.2280	0.5182	0.087*
C18	1.2649 (4)	0.2590 (4)	0.49373 (13)	0.0627 (8)
C19	1.3648 (4)	0.3074 (4)	0.44140 (13)	0.0669 (8)
H19	1.4922	0.3023	0.4483	0.080*
C20	1.2727 (4)	0.3637 (4)	0.37860 (13)	0.0670 (8)
H20	1.3402	0.3975	0.3434	0.080*
C21	1.5276 (4)	0.2114 (4)	0.57277 (13)	0.0959 (11)
H21A	1.6282	0.1171	0.5524	0.144*
H21B	1.5552	0.1853	0.6200	0.144*
H21C	1.5251	0.3366	0.5558	0.144*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0551 (15)	0.0683 (17)	0.0543 (15)	−0.0171 (13)	−0.0062 (11)	−0.0058 (12)
N2	0.0634 (16)	0.0769 (18)	0.0557 (15)	−0.0256 (14)	−0.0110 (12)	−0.0096 (12)
O1	0.0562 (12)	0.1062 (17)	0.0539 (12)	−0.0218 (11)	−0.0072 (9)	−0.0116 (10)
O2	0.0725 (14)	0.1078 (18)	0.0599 (12)	−0.0379 (12)	−0.0111 (10)	−0.0041 (11)
O3	0.0699 (13)	0.140 (2)	0.0495 (12)	−0.0358 (13)	0.0041 (10)	−0.0105 (11)
O4	0.0660 (14)	0.128 (2)	0.0742 (14)	−0.0307 (13)	−0.0134 (11)	−0.0099 (12)
O5	0.0537 (12)	0.150 (2)	0.0738 (13)	−0.0519 (13)	0.0011 (9)	−0.0124 (12)
O6	0.0790 (15)	0.132 (2)	0.0708 (14)	−0.0603 (14)	−0.0180 (11)	0.0084 (12)
C1	0.0641 (19)	0.078 (2)	0.0539 (18)	−0.0198 (17)	−0.0075 (14)	−0.0074 (15)
C2	0.0615 (19)	0.083 (2)	0.0596 (18)	−0.0226 (17)	−0.0068 (14)	−0.0071 (15)
C3	0.0636 (19)	0.066 (2)	0.0589 (18)	−0.0185 (16)	−0.0073 (14)	−0.0055 (14)
C4	0.068 (2)	0.065 (2)	0.0620 (18)	−0.0220 (16)	−0.0093 (14)	−0.0086 (14)
C5	0.064 (2)	0.072 (2)	0.0655 (19)	−0.0217 (17)	−0.0124 (15)	−0.0053 (15)
C6	0.0586 (18)	0.069 (2)	0.0511 (17)	−0.0209 (16)	0.0053 (14)	−0.0088 (14)
C7	0.0553 (18)	0.0558 (19)	0.0467 (16)	−0.0212 (15)	−0.0018 (14)	−0.0061 (13)
C8	0.0620 (19)	0.072 (2)	0.0433 (17)	−0.0251 (16)	0.0005 (14)	−0.0045 (14)
C9	0.0581 (19)	0.104 (3)	0.0542 (19)	−0.0273 (18)	0.0038 (14)	−0.0135 (16)
C10	0.0546 (19)	0.068 (2)	0.063 (2)	−0.0212 (16)	−0.0073 (16)	−0.0059 (15)
C11	0.073 (2)	0.082 (2)	0.0518 (18)	−0.0293 (18)	−0.0038 (16)	−0.0088 (15)
C12	0.0633 (19)	0.083 (2)	0.0512 (18)	−0.0259 (17)	0.0038 (14)	−0.0120 (15)
C13	0.089 (2)	0.100 (3)	0.080 (2)	−0.029 (2)	−0.0296 (18)	−0.0106 (19)
C14	0.0625 (19)	0.070 (2)	0.0630 (19)	−0.0279 (17)	0.0019 (15)	−0.0109 (15)
C15	0.0495 (17)	0.0574 (19)	0.0555 (17)	−0.0213 (14)	0.0037 (13)	−0.0139 (13)
C16	0.0417 (16)	0.079 (2)	0.0681 (19)	−0.0269 (15)	0.0022 (14)	−0.0186 (15)
C17	0.0602 (19)	0.108 (3)	0.0597 (19)	−0.0455 (18)	0.0014 (15)	−0.0068 (17)
C18	0.0563 (18)	0.073 (2)	0.0621 (19)	−0.0302 (16)	−0.0057 (15)	−0.0061 (15)
C19	0.0470 (17)	0.083 (2)	0.076 (2)	−0.0294 (16)	0.0010 (15)	−0.0134 (16)
C20	0.0539 (18)	0.085 (2)	0.069 (2)	−0.0357 (17)	0.0067 (14)	−0.0086 (16)
C21	0.075 (2)	0.123 (3)	0.097 (2)	−0.054 (2)	−0.0304 (18)	0.003 (2)

Geometric parameters (Å, º) top

N1—C6	1.280 (2)	C6—C7	1.449 (3)
N1—O1	1.396 (2)	C6—H6	0.9300
N2—C14	1.276 (3)	C7—C12	1.383 (3)
N2—O2	1.395 (2)	C7—C8	1.398 (3)
O1—C1	1.432 (2)	C8—C9	1.364 (3)
O2—C5	1.432 (3)	C9—C10	1.378 (3)
O3—C8	1.354 (2)	C9—H9	0.9300
O3—H3	0.8200	C10—C11	1.379 (3)
O4—C10	1.367 (3)	C11—C12	1.382 (3)
O4—C13	1.420 (3)	C11—H11	0.9300
O5—C16	1.363 (2)	C12—H12	0.9300
O5—H5	0.8200	C13—H13A	0.9600
O6—C18	1.365 (3)	C13—H13B	0.9600
O6—C21	1.431 (3)	C13—H13C	0.9600
C1—C2	1.493 (3)	C14—C15	1.441 (3)
C1—H1A	0.9700	C14—H14	0.9300
C1—H1B	0.9700	C15—C20	1.387 (3)
C2—C3	1.506 (3)	C15—C16	1.405 (3)
C2—H2A	0.9700	C16—C17	1.371 (3)
C2—H2B	0.9700	C17—C18	1.376 (3)
C3—C4	1.513 (3)	C17—H17	0.9300
C3—H3A	0.9700	C18—C19	1.377 (3)
C3—H3B	0.9700	C19—C20	1.378 (3)
C4—C5	1.490 (3)	C19—H19	0.9300
C4—H4A	0.9700	C20—H20	0.9300
C4—H4B	0.9700	C21—H21A	0.9600
C5—H5A	0.9700	C21—H21B	0.9600
C5—H5B	0.9700	C21—H21C	0.9600

C6—N1—O1	112.7 (2)	C9—C8—C7	120.7 (2)
C14—N2—O2	111.7 (2)	C8—C9—C10	120.9 (3)
N1—O1—C1	109.48 (18)	C8—C9—H9	119.5
N2—O2—C5	110.15 (19)	C10—C9—H9	119.5
C8—O3—H3	109.5	O4—C10—C9	115.7 (3)
C10—O4—C13	118.4 (2)	O4—C10—C11	124.0 (3)
C16—O5—H5	109.5	C9—C10—C11	120.3 (2)
C18—O6—C21	117.9 (2)	C10—C11—C12	117.9 (2)
O1—C1—C2	107.6 (2)	C10—C11—H11	121.1
O1—C1—H1A	110.2	C12—C11—H11	121.1
C2—C1—H1A	110.2	C11—C12—C7	123.3 (3)
O1—C1—H1B	110.2	C11—C12—H12	118.4
C2—C1—H1B	110.2	C7—C12—H12	118.4
H1A—C1—H1B	108.5	O4—C13—H13A	109.5
C1—C2—C3	114.5 (2)	O4—C13—H13B	109.5
C1—C2—H2A	108.6	H13A—C13—H13B	109.5
C3—C2—H2A	108.6	O4—C13—H13C	109.5
C1—C2—H2B	108.6	H13A—C13—H13C	109.5
C3—C2—H2B	108.6	H13B—C13—H13C	109.5
H2A—C2—H2B	107.6	N2—C14—C15	121.9 (2)
C2—C3—C4	113.2 (2)	N2—C14—H14	119.1
C2—C3—H3A	108.9	C15—C14—H14	119.1
C4—C3—H3A	108.9	C20—C15—C16	116.6 (2)
C2—C3—H3B	108.9	C20—C15—C14	120.6 (2)
C4—C3—H3B	108.9	C16—C15—C14	122.8 (2)
H3A—C3—H3B	107.8	O5—C16—C17	118.2 (2)
C5—C4—C3	113.1 (2)	O5—C16—C15	120.9 (2)
C5—C4—H4A	109.0	C17—C16—C15	121.0 (2)
C3—C4—H4A	109.0	C16—C17—C18	120.6 (2)
C5—C4—H4B	109.0	C16—C17—H17	119.7
C3—C4—H4B	109.0	C18—C17—H17	119.7
H4A—C4—H4B	107.8	O6—C18—C17	115.9 (2)
O2—C5—C4	108.8 (2)	O6—C18—C19	124.0 (2)
O2—C5—H5A	109.9	C17—C18—C19	120.1 (2)
C4—C5—H5A	109.9	C18—C19—C20	118.8 (2)
O2—C5—H5B	109.9	C18—C19—H19	120.6
C4—C5—H5B	109.9	C20—C19—H19	120.6
H5A—C5—H5B	108.3	C19—C20—C15	122.9 (2)
N1—C6—C7	120.5 (2)	C19—C20—H20	118.6
N1—C6—H6	119.8	C15—C20—H20	118.6
C7—C6—H6	119.8	O6—C21—H21A	109.5
C12—C7—C8	116.8 (2)	O6—C21—H21B	109.5
C12—C7—C6	120.5 (2)	H21A—C21—H21B	109.5
C8—C7—C6	122.6 (2)	O6—C21—H21C	109.5
O3—C8—C9	117.5 (2)	H21A—C21—H21C	109.5
O3—C8—C7	121.7 (2)	H21B—C21—H21C	109.5

C6—N1—O1—C1	−179.4 (2)	C9—C10—C11—C12	−0.1 (4)
C14—N2—O2—C5	−169.4 (2)	C10—C11—C12—C7	1.0 (4)
N1—O1—C1—C2	−179.9 (2)	C8—C7—C12—C11	−2.0 (4)
O1—C1—C2—C3	177.9 (2)	C6—C7—C12—C11	177.2 (3)
C1—C2—C3—C4	−174.9 (2)	O2—N2—C14—C15	−176.9 (2)
C2—C3—C4—C5	−178.3 (2)	N2—C14—C15—C20	179.5 (3)
N2—O2—C5—C4	−173.06 (19)	N2—C14—C15—C16	−0.6 (4)
C3—C4—C5—O2	−175.4 (2)	C20—C15—C16—O5	−179.7 (2)
O1—N1—C6—C7	178.8 (2)	C14—C15—C16—O5	0.4 (4)
N1—C6—C7—C12	−178.8 (2)	C20—C15—C16—C17	−0.3 (4)
N1—C6—C7—C8	0.4 (4)	C14—C15—C16—C17	179.8 (2)
C12—C7—C8—O3	−178.9 (2)	O5—C16—C17—C18	−179.6 (3)
C6—C7—C8—O3	1.9 (4)	C15—C16—C17—C18	0.9 (4)
C12—C7—C8—C9	2.3 (4)	C21—O6—C18—C17	−175.2 (3)
C6—C7—C8—C9	−176.9 (2)	C21—O6—C18—C19	5.0 (4)
O3—C8—C9—C10	179.5 (2)	C16—C17—C18—O6	178.8 (2)
C7—C8—C9—C10	−1.6 (4)	C16—C17—C18—C19	−1.4 (4)
C13—O4—C10—C9	−178.8 (2)	O6—C18—C19—C20	−179.0 (2)
C13—O4—C10—C11	0.9 (4)	C17—C18—C19—C20	1.2 (4)
C8—C9—C10—O4	−179.8 (3)	C18—C19—C20—C15	−0.6 (4)
C8—C9—C10—C11	0.5 (4)	C16—C15—C20—C19	0.1 (4)
O4—C10—C11—C12	−179.8 (2)	C14—C15—C20—C19	−180.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1	0.82	1.90	2.610 (3)	144
O5—H5···N2	0.82	1.90	2.628 (3)	147
O3—H3···O3ⁱ	0.82	2.68	3.045 (3)	109
C2—H2A···O3ⁱⁱ	0.97	2.58	3.533 (4)	168
C19—H19···O5ⁱⁱ	0.93	2.44	3.300 (4)	154

Symmetry codes: (i) −x−1, −y+2, −z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₆N₂O₆
M_r	402.44
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.3324 (15), 7.6214 (17), 20.372 (3)
α, β, γ (°)	81.525 (1), 89.928 (2), 67.870 (1)
V (Å³)	1041.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.43 × 0.28 × 0.14

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.961, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	5481, 3618, 1641
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.124, 1.01
No. of reflections	3618
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.18

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
O3—H3···N1	0.820	1.900	2.610 (3)	144.22
O5—H5···N2	0.820	1.904	2.628 (3)	146.67
O3—H3···O3ⁱ	0.820	2.681	3.045 (3)	108.76
C2—H2A···O3ⁱⁱ	0.970	2.579	3.533 (4)	167.85
C19—H19···O5ⁱⁱ	0.930	2.438	3.300 (4)	154.02

Symmetry codes: (i) −x−1, −y+2, −z; (ii) x+1, y, z.

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

Akine, S., Taniguchi, T., Dong, W. K., Masubuchi, S. & Nabeshima, T. (2005). J. Org. Chem. 70, 1704–1711. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Volume 65| Part 5| May 2009| Page o1160

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

5,5′-Dimeth­­oxy-2,2′-[(pentane-1,5-diyl­di­oxy)bis­­(nitrilo­methyl­­idyne)]diphenol

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5,5′-Dimethoxy-2,2′-[(pentane-1,5-diyldioxy)bis(nitrilomethylidyne)]diphenol