5,5′-Dimeth­oxy-2,2′-[(nonane-1,9-diyldi­oxy)bis­(nitrilo­methyl­idyne)]diphenol

Li, L.; Ma, H.-Z.; Gao, S.-X.; Dong, W.-K.; Wu, J.-C.

doi:10.1107/S1600536809041038

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2771

https://doi.org/10.1107/S1600536809041038

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5,5′-Dimethoxy-2,2′-[(nonane-1,9-diyldioxy)bis(nitrilomethylidyne)]diphenol

Li Li,^a Hong-Zheng Ma,^b Su-Xia Gao,^c Wen-Kui Dong ^a ^* and Jian-Chao Wu ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China, ^bThe Five TBM, China Railway Tunnel Co. Ltd, Xinxiang 453000, People's Republic of China, and ^cSchool of Environmental Science and Municipal Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: dongwk@126.com

(Received 5 October 2009; accepted 8 October 2009; online 17 October 2009)

The molecule of the title compound, C₂₅H₃₄N₂O₆, adopts a fully extended configuration. The oxime (—CH=N—O—) group is coplanar with the aromatic ring and the two benzene rings are almost parallel, making a dihedral angle of 0.16 (3)°. In the crystal structure, strong intramolecular O—H⋯N hydrogen bonds generate six-membered S(6) ring motifs. Intermolecular C—H⋯O hydrogen bonds link each molecule to five others, forming an infinite three-dimensional supramolecular structure. The crystal is further stabilized by π–π stacking interactions between neighbouring benzene rings [centroid–centroid distance = 3.744 (2) Å].

Related literature

For related literature, see: Bernstein et al. (1995 ); Campbell et al. (2001 ); Desiraju (1996 ); Dong, He, Guan et al. (2008 ); Dong, He, Li et al. (2008 ); Dong, Li et al. (2008 ); Dong et al. (2009 ); Mohand et al. (1995 ); Sun et al. (2009 ).

Experimental

Crystal data

C₂₅H₃₄N₂O₆
M_r = 458.54
Triclinic, $[P \overline 1]$
a = 10.4701 (10) Å
b = 11.1249 (12) Å
c = 12.7602 (14) Å
α = 65.544 (1)°
β = 86.664 (2)°
γ = 67.085 (1)°
V = 1236.7 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.48 × 0.46 × 0.21 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.959, T_max = 0.982
6463 measured reflections
4303 independent reflections
2050 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.125
S = 1.05
4303 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.16 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
C17—H17B⋯O4ⁱ	0.96	2.68	3.369 (3)	129
C18—H18⋯O3ⁱⁱ	0.93	2.40	3.295 (3)	160
C25—H25C⋯O3ⁱⁱⁱ	0.96	2.59	3.541 (4)	170
C25—H25B⋯O6^iv	0.96	2.61	3.469 (4)	150
O3—H3⋯N1	0.82	1.86	2.583 (4)	147
O5—H5⋯N2	0.82	1.94	2.663 (4)	147
Symmetry codes: (i) -x, -y-2, -z+1; (ii) x+1, y+1, z; (iii) -x+1, -y, -z+2; (iv) -x+2, -y+2, -z+2.

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: https://doi.org/10.1107/S1600536809041038/hg2576sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041038/hg2576Isup2.hkl

checkCIF report

Comment top

Schiff bases are one of most important mixed-donor ligands in the field of modern coordination chemistry. They play an important role in the development of coordination chemistry related to biochemistry, synthesis and catalysis (Mohand et al., 1995; Campbell et al., 2001), enzymatic reactions, magnetism, and supramolecular architectures. Our group are interested in the synthesis and structure of salen-type bisoxime compounds formed by Schiff base reactions (Dong et al., 2008a; Dong et al., 2008b). Herein, we report, the synthesis and crystal structure of a salen-type bisoxime compound containing nine-methene bridge, 5,5'-dimethoxy-2,2'-[(nonane-1,9-diyldioxy)bis(nitrilomethylidyne)]diphenol.

The molecular structure of the title compound, C₂₅H₃₄N₂O₆, as shown in Fig. 1, adopts a linear configuration, which is similar to our previously reported compound (Sun et al., 2009). In the crystal unit, the oxime (–CH=N—O–) group is coplanar with the aromatic ring and the two benzene rings are approximately parallel, making a dihedral angle of 0.16 (3)°. The bond lengths and angles in the molecule are within normal ranges.

In the crystal structure, strong intramolecular O—H···N hydrogen bonds generate two six-membered rings, producing S(6) ring motifs (Fig. 1) (Bernstein et al., 1995). Intermolecular C—H···O hydrogen bonds (Fig. 2) link the each molecule to five others, foming an infinite three-dimensional supramolecular structure (Desiraju, 1996) (Fig. 3). The crystal is further stabilized by π-π stacking interactions between the neighbouring benzene rings (centroid-centroid distances = 3.744 (2) Å) (Fig. 4).

Related literature top

For related literature, see: Bernstein et al. (1995); Campbell et al. (2001); Desiraju (1996); Dong, He, Guan et al. (2008); Dong, He, Li et al. (2008); Dong, Li et al. (2008); Dong et al. (2009); Mohand et al. (1995); Sun et al. (2009).

Experimental top

5,5'-Dimethoxy-2,2'-[(nonane-1,9-diyldioxy)bis(nitrilomethylidyne)]diphenol was synthesized according to an analogous method reported earlier (Dong et al., 2008c; Dong et al., 2009). To an ethanol solution (5 ml) of 4-methoxy-2-hydroxybenzaldehyde (159.5 mg, 1.05 mmol) was added an ethanol solution (5 ml) of 1,9-bis(aminooxy)nonane (99.0 mg, 0.52 mmol). The reaction mixture was stirred at 328 K for 8 h. The formed precipitate was separated by filtration under reduced pressure, and washed successively with ethanol and ethanol-hexane (1:4), respectively. The product was dried under vacuum to yield 155.4 mg of the title compound. Yield, 32.3%. m. p. 465–467 K. Anal. Calcd. for C₂₅H₃₄N₂O₆: C, 62.67; H, 6.51; N, 9.96. Found: C, 62.79; H, 6.68; N, 9.83.

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

Structure description top

For related literature, see: Bernstein et al. (1995); Campbell et al. (2001); Desiraju (1996); Dong, He, Guan et al. (2008); Dong, He, Li et al. (2008); Dong, Li et al. (2008); Dong et al. (2009); Mohand et al. (1995); Sun et al. (2009).

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 molecular structure of the title compound with atom numbering scheme. 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.
	Fig. 3. Three-dimensional packing diagram of the title compound, showing the layer configuration along b axis.
	Fig. 4. Part π···π stacking interactions in the title compound (as shown as dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

5,5'-Dimethoxy-2,2'-[(nonane-1,9-diyldioxy)bis(nitrilomethylidyne)]diphenol top

Crystal data top

C₂₅H₃₄N₂O₆	Z = 2
M_r = 458.54	F(000) = 492
Triclinic, P1	D_x = 1.231 Mg m⁻³
Hall symbol: -P 1	Melting point = 465–467 K
a = 10.4701 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1249 (12) Å	Cell parameters from 1465 reflections
c = 12.7602 (14) Å	θ = 2.2–22.6°
α = 65.544 (1)°	µ = 0.09 mm⁻¹
β = 86.664 (2)°	T = 298 K
γ = 67.085 (1)°	Block-like, colorless
V = 1236.7 (2) Å³	0.48 × 0.46 × 0.21 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4303 independent reflections
Radiation source: fine-focus sealed tube	2050 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.959, T_max = 0.982	k = −13→13
6463 measured reflections	l = −9→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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0355P)²] where P = (F_o² + 2F_c²)/3
4303 reflections	(Δ/σ)_max < 0.001
300 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₅H₃₄N₂O₆	γ = 67.085 (1)°
M_r = 458.54	V = 1236.7 (2) Å³
Triclinic, P1	Z = 2
a = 10.4701 (10) Å	Mo Kα radiation
b = 11.1249 (12) Å	µ = 0.09 mm⁻¹
c = 12.7602 (14) Å	T = 298 K
α = 65.544 (1)°	0.48 × 0.46 × 0.21 mm
β = 86.664 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4303 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2050 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.982	R_int = 0.036
6463 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.05	Δρ_max = 0.16 e Å⁻³
4303 reflections	Δρ_min = −0.18 e Å⁻³
300 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	0.2659 (2)	−0.4795 (2)	0.60645 (19)	0.0660 (6)
N2	0.7314 (2)	0.4634 (2)	0.87062 (18)	0.0634 (6)
O1	0.34859 (18)	−0.40335 (19)	0.59502 (16)	0.0766 (6)
O2	0.72925 (18)	0.37983 (19)	0.81319 (15)	0.0766 (6)
O3	0.07937 (17)	−0.58178 (17)	0.68503 (15)	0.0769 (6)
H3	0.1269	−0.5362	0.6794	0.115*
O4	0.02223 (19)	−0.88667 (18)	0.53611 (16)	0.0767 (6)
O5	0.67807 (19)	0.59846 (18)	1.00861 (15)	0.0830 (6)
H5	0.6699	0.5472	0.9805	0.124*
O6	0.9436 (2)	0.87142 (19)	0.98147 (17)	0.0857 (6)
C1	0.3053 (3)	−0.3278 (3)	0.6680 (2)	0.0719 (8)
H1A	0.3108	−0.3948	0.7478	0.086*
H1B	0.2098	−0.2567	0.6422	0.086*
C2	0.4015 (3)	−0.2568 (3)	0.6585 (2)	0.0746 (8)
H2A	0.3948	−0.1920	0.5777	0.089*
H2B	0.4963	−0.3301	0.6813	0.089*
C3	0.3762 (3)	−0.1723 (3)	0.7304 (2)	0.0681 (8)
H3A	0.2810	−0.0999	0.7097	0.082*
H3B	0.3871	−0.2369	0.8119	0.082*
C4	0.4758 (2)	−0.0993 (3)	0.7122 (2)	0.0659 (7)
H4A	0.5705	−0.1727	0.7337	0.079*
H4B	0.4661	−0.0374	0.6302	0.079*
C5	0.4563 (2)	−0.0103 (2)	0.7788 (2)	0.0656 (7)
H5A	0.4717	−0.0727	0.8612	0.079*
H5B	0.3605	0.0606	0.7605	0.079*
C6	0.5536 (3)	0.0667 (2)	0.7526 (2)	0.0660 (7)
H6A	0.6491	−0.0045	0.7689	0.079*
H6B	0.5367	0.1300	0.6703	0.079*
C7	0.5397 (3)	0.1549 (3)	0.8196 (2)	0.0695 (8)
H7A	0.5573	0.0922	0.9019	0.083*
H7B	0.4446	0.2269	0.8032	0.083*
C8	0.6393 (3)	0.2293 (3)	0.7898 (2)	0.0715 (8)
H8A	0.7337	0.1568	0.8035	0.086*
H8B	0.6196	0.2932	0.7076	0.086*
C9	0.6336 (3)	0.3152 (3)	0.8561 (2)	0.0728 (8)
H9A	0.5401	0.3885	0.8445	0.087*
H9B	0.6594	0.2528	0.9384	0.087*
C10	0.2957 (2)	−0.5469 (3)	0.5419 (2)	0.0622 (7)
H10	0.3658	−0.5407	0.4943	0.075*
C11	0.2216 (2)	−0.6325 (2)	0.5424 (2)	0.0525 (6)
C12	0.1170 (2)	−0.6471 (2)	0.6125 (2)	0.0510 (6)
C13	0.0470 (2)	−0.7291 (2)	0.6116 (2)	0.0565 (7)
H13	−0.0242	−0.7359	0.6578	0.068*
C14	0.0836 (3)	−0.8008 (2)	0.5414 (2)	0.0566 (7)
C15	0.1875 (3)	−0.7888 (3)	0.4717 (2)	0.0669 (8)
H15	0.2120	−0.8371	0.4243	0.080*
C16	0.2542 (3)	−0.7060 (3)	0.4726 (2)	0.0656 (7)
H16	0.3239	−0.6983	0.4248	0.079*
C17	−0.0791 (3)	−0.9095 (3)	0.6107 (2)	0.0883 (9)
H17A	−0.0392	−0.9493	0.6897	0.132*
H17B	−0.1096	−0.9755	0.6006	0.132*
H17C	−0.1575	−0.8194	0.5927	0.132*
C18	0.8248 (3)	0.5120 (2)	0.8369 (2)	0.0580 (7)
H18	0.8792	0.4871	0.7829	0.070*
C19	0.8512 (2)	0.6043 (2)	0.8781 (2)	0.0511 (6)
C20	0.7786 (2)	0.6443 (3)	0.9615 (2)	0.0573 (7)
C21	0.8074 (3)	0.7331 (3)	0.9981 (2)	0.0632 (7)
H21	0.7582	0.7594	1.0537	0.076*
C22	0.9084 (3)	0.7820 (3)	0.9523 (2)	0.0606 (7)
C23	0.9834 (3)	0.7427 (3)	0.8705 (2)	0.0670 (8)
H23	1.0532	0.7748	0.8405	0.080*
C24	0.9532 (3)	0.6557 (2)	0.8348 (2)	0.0617 (7)
H24	1.0030	0.6301	0.7792	0.074*
C25	0.8799 (3)	0.9062 (3)	1.0714 (3)	0.1070 (12)
H25A	0.7806	0.9555	1.0499	0.161*
H25B	0.9151	0.9673	1.0842	0.161*
H25C	0.9005	0.8193	1.1412	0.161*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0605 (15)	0.0674 (15)	0.0816 (16)	−0.0295 (13)	0.0040 (13)	−0.0379 (14)
N2	0.0647 (15)	0.0654 (14)	0.0738 (15)	−0.0312 (13)	0.0088 (13)	−0.0376 (13)
O1	0.0729 (13)	0.0867 (13)	0.0998 (14)	−0.0434 (11)	0.0196 (11)	−0.0570 (12)
O2	0.0791 (13)	0.0933 (14)	0.0953 (14)	−0.0536 (12)	0.0278 (12)	−0.0592 (12)
O3	0.0862 (13)	0.0910 (13)	0.0914 (13)	−0.0466 (11)	0.0382 (12)	−0.0665 (12)
O4	0.0870 (14)	0.0836 (14)	0.0873 (14)	−0.0448 (12)	0.0190 (12)	−0.0527 (12)
O5	0.0860 (14)	0.1028 (15)	0.0933 (14)	−0.0538 (12)	0.0403 (12)	−0.0610 (12)
O6	0.1094 (16)	0.0787 (13)	0.0937 (15)	−0.0487 (13)	0.0137 (13)	−0.0494 (12)
C1	0.0660 (19)	0.0783 (19)	0.088 (2)	−0.0345 (16)	0.0122 (17)	−0.0460 (18)
C2	0.0654 (19)	0.0794 (19)	0.093 (2)	−0.0348 (17)	0.0070 (17)	−0.0434 (18)
C3	0.0597 (18)	0.0706 (18)	0.084 (2)	−0.0268 (16)	0.0026 (16)	−0.0405 (17)
C4	0.0593 (18)	0.0659 (18)	0.0772 (19)	−0.0237 (15)	−0.0022 (16)	−0.0347 (16)
C5	0.0592 (17)	0.0637 (17)	0.0777 (19)	−0.0250 (15)	0.0034 (15)	−0.0327 (16)
C6	0.0649 (19)	0.0628 (17)	0.0726 (19)	−0.0252 (15)	0.0001 (16)	−0.0303 (16)
C7	0.0700 (19)	0.0682 (18)	0.0774 (19)	−0.0329 (16)	0.0062 (17)	−0.0322 (16)
C8	0.0739 (19)	0.0740 (18)	0.0771 (19)	−0.0367 (17)	0.0091 (16)	−0.0352 (16)
C9	0.075 (2)	0.0714 (19)	0.089 (2)	−0.0382 (17)	0.0162 (18)	−0.0419 (18)
C10	0.0551 (17)	0.0641 (18)	0.0634 (18)	−0.0177 (15)	0.0060 (15)	−0.0289 (16)
C11	0.0466 (16)	0.0540 (16)	0.0557 (17)	−0.0151 (14)	0.0017 (14)	−0.0264 (14)
C12	0.0492 (16)	0.0474 (15)	0.0514 (16)	−0.0089 (13)	0.0013 (14)	−0.0256 (14)
C13	0.0568 (17)	0.0577 (16)	0.0588 (17)	−0.0221 (14)	0.0082 (14)	−0.0292 (15)
C14	0.0582 (17)	0.0511 (16)	0.0594 (18)	−0.0185 (14)	0.0016 (15)	−0.0251 (15)
C15	0.0669 (19)	0.080 (2)	0.0701 (19)	−0.0280 (16)	0.0146 (17)	−0.0486 (17)
C16	0.0576 (18)	0.0809 (19)	0.0643 (18)	−0.0245 (16)	0.0168 (15)	−0.0407 (17)
C17	0.103 (2)	0.091 (2)	0.095 (2)	−0.059 (2)	0.025 (2)	−0.0444 (19)
C18	0.0515 (17)	0.0588 (17)	0.0602 (17)	−0.0166 (14)	0.0030 (15)	−0.0268 (14)
C19	0.0462 (15)	0.0476 (15)	0.0546 (16)	−0.0142 (13)	0.0002 (14)	−0.0208 (14)
C20	0.0490 (16)	0.0572 (16)	0.0580 (17)	−0.0191 (14)	0.0094 (15)	−0.0201 (15)
C21	0.074 (2)	0.0568 (17)	0.0601 (17)	−0.0202 (16)	0.0069 (16)	−0.0315 (15)
C22	0.0676 (19)	0.0467 (16)	0.0613 (18)	−0.0192 (15)	−0.0061 (16)	−0.0192 (15)
C23	0.0651 (18)	0.0658 (18)	0.077 (2)	−0.0300 (16)	0.0125 (17)	−0.0332 (17)
C24	0.0611 (18)	0.0617 (17)	0.0643 (17)	−0.0230 (15)	0.0104 (15)	−0.0307 (15)
C25	0.161 (3)	0.102 (2)	0.091 (2)	−0.063 (2)	0.028 (2)	−0.064 (2)

Geometric parameters (Å, º) top

N1—C10	1.280 (3)	C7—H7B	0.9700
N1—O1	1.394 (2)	C8—C9	1.501 (3)
N2—C18	1.266 (3)	C8—H8A	0.9700
N2—O2	1.409 (2)	C8—H8B	0.9700
O1—C1	1.443 (3)	C9—H9A	0.9700
O2—C9	1.410 (3)	C9—H9B	0.9700
O3—C12	1.353 (2)	C10—C11	1.441 (3)
O3—H3	0.8200	C10—H10	0.9300
O4—C14	1.366 (3)	C11—C16	1.390 (3)
O4—C17	1.410 (3)	C11—C12	1.390 (3)
O5—C20	1.349 (3)	C12—C13	1.379 (3)
O5—H5	0.8200	C13—C14	1.377 (3)
O6—C22	1.369 (3)	C13—H13	0.9300
O6—C25	1.410 (3)	C14—C15	1.377 (3)
C1—C2	1.476 (3)	C15—C16	1.358 (3)
C1—H1A	0.9700	C15—H15	0.9300
C1—H1B	0.9700	C16—H16	0.9300
C2—C3	1.513 (3)	C17—H17A	0.9600
C2—H2A	0.9700	C17—H17B	0.9600
C2—H2B	0.9700	C17—H17C	0.9600
C3—C4	1.509 (3)	C18—C19	1.446 (3)
C3—H3A	0.9700	C18—H18	0.9300
C3—H3B	0.9700	C19—C24	1.385 (3)
C4—C5	1.504 (3)	C19—C20	1.394 (3)
C4—H4A	0.9700	C20—C21	1.384 (3)
C4—H4B	0.9700	C21—C22	1.367 (3)
C5—C6	1.512 (3)	C21—H21	0.9300
C5—H5A	0.9700	C22—C23	1.383 (3)
C5—H5B	0.9700	C23—C24	1.366 (3)
C6—C7	1.511 (3)	C23—H23	0.9300
C6—H6A	0.9700	C24—H24	0.9300
C6—H6B	0.9700	C25—H25A	0.9600
C7—C8	1.512 (3)	C25—H25B	0.9600
C7—H7A	0.9700	C25—H25C	0.9600

C10—N1—O1	112.5 (2)	C8—C9—H9A	110.4
C18—N2—O2	109.9 (2)	O2—C9—H9B	110.4
N1—O1—C1	108.68 (18)	C8—C9—H9B	110.4
N2—O2—C9	110.86 (18)	H9A—C9—H9B	108.6
C12—O3—H3	109.5	N1—C10—C11	120.6 (2)
C14—O4—C17	118.41 (19)	N1—C10—H10	119.7
C20—O5—H5	109.5	C11—C10—H10	119.7
C22—O6—C25	117.9 (2)	C16—C11—C12	117.1 (2)
O1—C1—C2	106.5 (2)	C16—C11—C10	120.6 (2)
O1—C1—H1A	110.4	C12—C11—C10	122.3 (2)
C2—C1—H1A	110.4	O3—C12—C13	116.9 (2)
O1—C1—H1B	110.4	O3—C12—C11	121.6 (2)
C2—C1—H1B	110.4	C13—C12—C11	121.5 (2)
H1A—C1—H1B	108.6	C14—C13—C12	119.3 (2)
C1—C2—C3	115.4 (2)	C14—C13—H13	120.4
C1—C2—H2A	108.4	C12—C13—H13	120.4
C3—C2—H2A	108.4	O4—C14—C15	116.1 (2)
C1—C2—H2B	108.4	O4—C14—C13	123.6 (2)
C3—C2—H2B	108.4	C15—C14—C13	120.3 (2)
H2A—C2—H2B	107.5	C16—C15—C14	119.7 (2)
C4—C3—C2	111.8 (2)	C16—C15—H15	120.2
C4—C3—H3A	109.3	C14—C15—H15	120.2
C2—C3—H3A	109.3	C15—C16—C11	122.2 (2)
C4—C3—H3B	109.3	C15—C16—H16	118.9
C2—C3—H3B	109.3	C11—C16—H16	118.9
H3A—C3—H3B	107.9	O4—C17—H17A	109.5
C5—C4—C3	115.4 (2)	O4—C17—H17B	109.5
C5—C4—H4A	108.4	H17A—C17—H17B	109.5
C3—C4—H4A	108.4	O4—C17—H17C	109.5
C5—C4—H4B	108.4	H17A—C17—H17C	109.5
C3—C4—H4B	108.4	H17B—C17—H17C	109.5
H4A—C4—H4B	107.5	N2—C18—C19	123.3 (2)
C4—C5—C6	113.3 (2)	N2—C18—H18	118.3
C4—C5—H5A	108.9	C19—C18—H18	118.3
C6—C5—H5A	108.9	C24—C19—C20	117.4 (2)
C4—C5—H5B	108.9	C24—C19—C18	119.8 (2)
C6—C5—H5B	108.9	C20—C19—C18	122.8 (2)
H5A—C5—H5B	107.7	O5—C20—C21	118.0 (2)
C7—C6—C5	115.0 (2)	O5—C20—C19	121.3 (2)
C7—C6—H6A	108.5	C21—C20—C19	120.8 (2)
C5—C6—H6A	108.5	C22—C21—C20	119.7 (2)
C7—C6—H6B	108.5	C22—C21—H21	120.1
C5—C6—H6B	108.5	C20—C21—H21	120.1
H6A—C6—H6B	107.5	C21—C22—O6	124.4 (3)
C6—C7—C8	112.7 (2)	C21—C22—C23	120.8 (2)
C6—C7—H7A	109.1	O6—C22—C23	114.8 (3)
C8—C7—H7A	109.1	C24—C23—C22	118.7 (3)
C6—C7—H7B	109.1	C24—C23—H23	120.7
C8—C7—H7B	109.1	C22—C23—H23	120.7
H7A—C7—H7B	107.8	C23—C24—C19	122.5 (2)
C9—C8—C7	115.3 (2)	C23—C24—H24	118.7
C9—C8—H8A	108.4	C19—C24—H24	118.7
C7—C8—H8A	108.4	O6—C25—H25A	109.5
C9—C8—H8B	108.4	O6—C25—H25B	109.5
C7—C8—H8B	108.4	H25A—C25—H25B	109.5
H8A—C8—H8B	107.5	O6—C25—H25C	109.5
O2—C9—C8	106.6 (2)	H25A—C25—H25C	109.5
O2—C9—H9A	110.4	H25B—C25—H25C	109.5

C10—N1—O1—C1	178.4 (2)	C12—C13—C14—C15	−1.0 (4)
C18—N2—O2—C9	175.3 (2)	O4—C14—C15—C16	−179.6 (2)
N1—O1—C1—C2	176.5 (2)	C13—C14—C15—C16	0.1 (4)
O1—C1—C2—C3	−179.1 (2)	C14—C15—C16—C11	0.3 (4)
C1—C2—C3—C4	−178.0 (2)	C12—C11—C16—C15	0.1 (4)
C2—C3—C4—C5	178.9 (2)	C10—C11—C16—C15	179.3 (2)
C3—C4—C5—C6	−176.9 (2)	O2—N2—C18—C19	178.71 (19)
C4—C5—C6—C7	−178.7 (2)	N2—C18—C19—C24	−178.5 (2)
C5—C6—C7—C8	−180.0 (2)	N2—C18—C19—C20	2.1 (4)
C6—C7—C8—C9	−178.3 (2)	C24—C19—C20—O5	−179.7 (2)
N2—O2—C9—C8	−179.98 (18)	C18—C19—C20—O5	−0.2 (3)
C7—C8—C9—O2	−177.8 (2)	C24—C19—C20—C21	0.6 (3)
O1—N1—C10—C11	179.65 (19)	C18—C19—C20—C21	−179.9 (2)
N1—C10—C11—C16	−179.8 (2)	O5—C20—C21—C22	−179.9 (2)
N1—C10—C11—C12	−0.7 (4)	C19—C20—C21—C22	−0.2 (4)
C16—C11—C12—O3	178.9 (2)	C20—C21—C22—O6	179.2 (2)
C10—C11—C12—O3	−0.3 (3)	C20—C21—C22—C23	−0.7 (4)
C16—C11—C12—C13	−1.0 (3)	C25—O6—C22—C21	5.4 (4)
C10—C11—C12—C13	179.8 (2)	C25—O6—C22—C23	−174.7 (2)
O3—C12—C13—C14	−178.4 (2)	C21—C22—C23—C24	1.1 (4)
C11—C12—C13—C14	1.5 (3)	O6—C22—C23—C24	−178.8 (2)
C17—O4—C14—C15	176.3 (2)	C22—C23—C24—C19	−0.6 (4)
C17—O4—C14—C13	−3.4 (3)	C20—C19—C24—C23	−0.2 (3)
C12—C13—C14—O4	178.7 (2)	C18—C19—C24—C23	−179.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···O4ⁱ	0.96	2.68	3.369 (3)	129
C18—H18···O3ⁱⁱ	0.93	2.40	3.295 (3)	160
C25—H25C···O3ⁱⁱⁱ	0.96	2.59	3.541 (4)	170
C25—H25B···O6^iv	0.96	2.61	3.469 (4)	150
O3—H3···N1	0.82	1.86	2.583 (4)	147
O5—H5···N2	0.82	1.94	2.663 (4)	147

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

Experimental details

Crystal data
Chemical formula	C₂₅H₃₄N₂O₆
M_r	458.54
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.4701 (10), 11.1249 (12), 12.7602 (14)
α, β, γ (°)	65.544 (1), 86.664 (2), 67.085 (1)
V (Å³)	1236.7 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.48 × 0.46 × 0.21

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.959, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	6463, 4303, 2050
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.125, 1.05
No. of reflections	4303
No. of parameters	300
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −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
C17—H17B···O4ⁱ	0.96	2.68	3.369 (3)	129.1
C18—H18···O3ⁱⁱ	0.93	2.40	3.295 (3)	160.4
C25—H25C···O3ⁱⁱⁱ	0.96	2.59	3.541 (4)	170.1
C25—H25B···O6^iv	0.96	2.61	3.469 (4)	149.8
O3—H3···N1	0.820	1.858	2.583 (4)	146.69
O5—H5···N2	0.820	1.939	2.663 (4)	146.83

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

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (grant No. 0904-11) and the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University, which are gratefully acknowledged.

References

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

5,5′-Dimeth­­oxy-2,2′-[(nonane-1,9-diyldi­­oxy)bis­­(nitrilo­methyl­­idyne)]diphenol

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Experimental

Crystal data

Data collection

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organic compounds

5,5′-Dimethoxy-2,2′-[(nonane-1,9-diyldioxy)bis(nitrilomethylidyne)]diphenol