4,4′-Dimethyl-2,2′-[(3-aza­pentane-1,5-di­yl)bis­(nitrilo­methyl­idyne)]diphenol

Dang, F.-F.; Wang, X.-W.; Yang, Q.-C.; Han, G.-P.

doi:10.1107/S1600536808018837

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1352

doi:10.1107/S1600536808018837

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4,4′-Dimethyl-2,2′-[(3-azapentane-1,5-diyl)bis(nitrilomethylidyne)]diphenol

Fang-Fang Dang,^a ^* Xin-Wei Wang,^b Qing-Cui Yang ^a and Guo-Ping Han ^a

^aSchool of Science, Xi'an University of Architecture and Technology, Xi'an 710055, People's Republic of China, and ^bXi'an LiBang Pharmaceutical Co. Ltd, Xi'an 710086, People's Republic of China
^*Correspondence e-mail: fangfangdang@yahoo.com.cn

(Received 14 June 2008; accepted 22 June 2008; online 28 June 2008)

In the crystal structure of the title Schiff base, C₂₀H₂₅N₃O₂, the salicylaldimine groups at each end of the molecule are essentially planar and make a dihedral angle of 84.94 (3)° with each other. There are strong intramolecular O—H⋯N hydrogen bonds and a weak intermolecular N—H⋯O hydrogen bond.

Related literature

For related literature, see: Rodriguez de Barbarin et al. (1994 ).

Experimental

Crystal data

C₂₀H₂₅N₃O₂
M_r = 339.43
Orthorhombic, P c a 2₁
a = 9.132 (4) Å
b = 5.834 (3) Å
c = 34.365 (16) Å
V = 1830.8 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 (2) K
0.34 × 0.32 × 0.28 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.970, T_max = 0.981
14593 measured reflections
2125 independent reflections
1867 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.108
S = 1.07
2125 reflections
228 parameters
1 restraint
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
O1—H1A⋯N1	0.82	1.89	2.614 (4)	146
O2—H2A⋯N2	0.82	1.88	2.602 (3)	146
N3—H3A⋯O1ⁱ	0.86	2.54	3.140 (3)	128
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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/S1600536808018837/is2306sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018837/is2306Isup2.hkl

checkCIF report

Comment top

It was reported that zinc coordinated by phenolate groups in a Schiff-base ligand can act as a nucleophile to catalyze ester hydrolysis (Rodriguez de Barbarin et al., 1994). These results promoted us to investigate linear amine-phenol ligands obtained by reducing Schiff bases, which have greater flexibility, better water solubility and more inertness to hydrolytic decomposition than corresponding Schiff bases. While a number of their complexes with transition metals and main group metals have been reported, the crystal structures of these Schiff-base ligands remain relatively unexplored. So we present here the crystal structure of the title compound, N,N'-bis(5-methylsalicylidene)-1,5-diamino-3-azapentane, (I).

The molecular structure of (I) is illustrated in Fig. 1. Compound (I) is a typical salicylaldehyde schiff derivative with normal geometric parameters. The two pendant moieties attached to the ends of the C—C—N—C—C backbone adopt a cis conformation. The N3 atom exhibits tetrahedral sp³ hybridization, whereas the two amide N atoms display planar sp² hybridization. The C8—N1 and C13—N2 bonds show the expected double-bond character. In our case, the salicylaldimine moiety is nearly planar. The dihedral angle between the salicylaldimine groups is 84.94 (3)°. The crystal structure of (I) is stabilized by intramolecular O—H···N hydrogen bonds and an intermolecular N—H···O hydrogen bond (Table 1).

Related literature top

For related literature, see: Rodriguez de Barbarin et al. (1994).

Experimental top

N-(2-aminoethyl)ethane-1,2-diamine (0.01 mol, 1.03 g) and 2-hydroxy-5-methylbenzaldehyde (0.02 mol, 2.72 g) were dissolved in ethanol and the solution was refluxed for 1 h. After evaporation, a crude product was recrystallized twice from ethanol to give a pure yellow product. Yield: 80.5%. Calcd. for C₂₀H₂₅N₃O₂: C 70.77, H 7.42, N 12.38; Found: C 71.02, H 7.47, N 12.27%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.

4,4'-Dimethyl-2,2'-[(3-azapentane-1,5-diyl)bis(nitrilomethylidyne)]diphenol top

Crystal data top

C₂₀H₂₅N₃O₂	F(000) = 728
M_r = 339.43	D_x = 1.231 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2105 reflections
a = 9.132 (4) Å	θ = 1.0–27.5°
b = 5.834 (3) Å	µ = 0.08 mm⁻¹
c = 34.365 (16) Å	T = 296 K
V = 1830.8 (15) Å³	Block, yellow
Z = 4	0.34 × 0.32 × 0.28 mm

Data collection top

Bruker APEXII area-detector diffractometer	2125 independent reflections
Radiation source: fine-focus sealed tube	1867 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.970, T_max = 0.981	k = −7→7
14593 measured reflections	l = −44→44

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0588P)² + 0.2052P] where P = (F_o² + 2F_c²)/3
2125 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₀H₂₅N₃O₂	V = 1830.8 (15) Å³
M_r = 339.43	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 9.132 (4) Å	µ = 0.08 mm⁻¹
b = 5.834 (3) Å	T = 296 K
c = 34.365 (16) Å	0.34 × 0.32 × 0.28 mm

Data collection top

Bruker APEXII area-detector diffractometer	2125 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1867 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.981	R_int = 0.031
14593 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.108	H-atom parameters constrained
S = 1.07	Δρ_max = 0.15 e Å⁻³
2125 reflections	Δρ_min = −0.18 e Å⁻³
228 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
O1	0.8321 (3)	1.4932 (4)	0.36346 (6)	0.0766 (7)
H1A	0.8862	1.4181	0.3493	0.115*
O2	0.7661 (2)	0.0213 (3)	0.18913 (5)	0.0594 (5)
H2A	0.8305	0.0960	0.1999	0.089*
N1	1.0105 (2)	1.1600 (4)	0.34511 (6)	0.0506 (5)
N2	0.9202 (2)	0.3855 (3)	0.20445 (5)	0.0479 (4)
N3	1.0062 (2)	0.7202 (3)	0.29474 (6)	0.0520 (5)
H3A	1.0210	0.6583	0.3171	0.062*
C1	0.8251 (3)	1.0370 (4)	0.43648 (7)	0.0455 (5)
H1C	0.8686	0.8960	0.4416	0.055*
C2	0.6782 (4)	0.9888 (6)	0.49830 (9)	0.0762 (9)
H2B	0.7544	0.8830	0.5051	0.114*
H2C	0.5895	0.9059	0.4931	0.114*
H2D	0.6622	1.0933	0.5195	0.114*
C3	0.7226 (3)	1.1209 (4)	0.46259 (7)	0.0495 (6)
C4	0.6605 (3)	1.3338 (5)	0.45429 (7)	0.0545 (6)
H4A	0.5923	1.3947	0.4715	0.065*
C5	0.6967 (3)	1.4566 (4)	0.42153 (8)	0.0563 (6)
H5A	0.6526	1.5977	0.4170	0.068*
C6	0.7992 (3)	1.3710 (4)	0.39506 (7)	0.0487 (5)
C7	0.8657 (2)	1.1551 (4)	0.40291 (6)	0.0399 (5)
C8	0.9752 (2)	1.0605 (4)	0.37676 (7)	0.0437 (5)
H8A	1.0208	0.9233	0.3833	0.052*
C9	1.1263 (3)	1.0645 (5)	0.32037 (7)	0.0584 (7)
H9A	1.1836	0.9560	0.3354	0.070*
H9B	1.1911	1.1871	0.3122	0.070*
C10	1.0648 (3)	0.9444 (4)	0.28455 (7)	0.0532 (6)
H10A	0.9879	1.0376	0.2732	0.064*
H10B	1.1416	0.9266	0.2653	0.064*
C11	0.9210 (3)	0.6085 (4)	0.26450 (6)	0.0472 (5)
H11A	0.8477	0.7152	0.2550	0.057*
H11B	0.8698	0.4788	0.2758	0.057*
C12	1.0123 (3)	0.5243 (5)	0.23003 (7)	0.0521 (6)
H12A	1.0510	0.6543	0.2158	0.063*
H12B	1.0940	0.4335	0.2394	0.063*
C13	0.8784 (3)	0.4705 (4)	0.17204 (7)	0.0441 (5)
H13A	0.9125	0.6143	0.1647	0.053*
C14	0.7784 (2)	0.3473 (3)	0.14626 (6)	0.0412 (5)
C15	0.7306 (3)	0.4500 (4)	0.11167 (7)	0.0466 (5)
H15A	0.7683	0.5925	0.1048	0.056*
C16	0.5766 (4)	0.4651 (6)	0.05050 (9)	0.0746 (8)
H16A	0.4734	0.4399	0.0474	0.112*
H16B	0.6279	0.4036	0.0285	0.112*
H16C	0.5955	0.6266	0.0524	0.112*
C17	0.6291 (3)	0.3464 (4)	0.08737 (7)	0.0519 (6)
C18	0.5756 (3)	0.1310 (4)	0.09836 (8)	0.0562 (6)
H18A	0.5074	0.0582	0.0825	0.067*
C19	0.6215 (3)	0.0237 (4)	0.13212 (8)	0.0534 (6)
H19A	0.5838	−0.1193	0.1387	0.064*
C20	0.7242 (3)	0.1288 (4)	0.15635 (7)	0.0448 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0892 (16)	0.0680 (11)	0.0725 (13)	0.0077 (11)	0.0161 (12)	0.0338 (10)
O2	0.0733 (12)	0.0477 (9)	0.0574 (10)	0.0009 (8)	0.0025 (9)	0.0103 (8)
N1	0.0448 (10)	0.0629 (12)	0.0440 (10)	−0.0085 (9)	0.0049 (8)	−0.0061 (9)
N2	0.0467 (10)	0.0535 (11)	0.0434 (10)	0.0017 (9)	0.0034 (9)	−0.0054 (9)
N3	0.0551 (11)	0.0628 (12)	0.0381 (9)	−0.0069 (10)	−0.0017 (9)	0.0057 (9)
C1	0.0484 (13)	0.0446 (11)	0.0435 (12)	0.0005 (9)	−0.0054 (10)	0.0057 (9)
C2	0.091 (2)	0.085 (2)	0.0526 (15)	−0.0057 (18)	0.0175 (17)	0.0134 (15)
C3	0.0516 (14)	0.0570 (13)	0.0400 (12)	−0.0081 (11)	0.0041 (10)	0.0013 (10)
C4	0.0518 (14)	0.0562 (14)	0.0554 (14)	−0.0016 (11)	0.0111 (11)	−0.0116 (11)
C5	0.0554 (15)	0.0471 (12)	0.0664 (16)	0.0058 (11)	0.0051 (13)	0.0010 (11)
C6	0.0491 (13)	0.0460 (12)	0.0511 (12)	−0.0032 (10)	−0.0004 (10)	0.0066 (10)
C7	0.0378 (11)	0.0429 (10)	0.0391 (11)	−0.0038 (8)	−0.0007 (9)	−0.0001 (8)
C8	0.0377 (11)	0.0502 (12)	0.0432 (11)	−0.0037 (9)	−0.0034 (9)	−0.0039 (9)
C9	0.0437 (13)	0.0815 (17)	0.0501 (13)	−0.0115 (13)	0.0066 (11)	−0.0145 (13)
C10	0.0551 (14)	0.0640 (14)	0.0405 (12)	−0.0100 (11)	0.0078 (11)	−0.0025 (11)
C11	0.0450 (12)	0.0540 (12)	0.0427 (12)	−0.0070 (10)	0.0053 (10)	−0.0001 (10)
C12	0.0410 (11)	0.0667 (14)	0.0487 (13)	0.0014 (11)	0.0006 (10)	−0.0066 (11)
C13	0.0424 (11)	0.0437 (11)	0.0463 (12)	−0.0010 (9)	0.0062 (9)	−0.0030 (9)
C14	0.0428 (11)	0.0384 (10)	0.0422 (11)	0.0013 (9)	0.0085 (9)	−0.0041 (9)
C15	0.0522 (13)	0.0417 (11)	0.0460 (12)	−0.0025 (10)	0.0059 (10)	−0.0008 (9)
C16	0.089 (2)	0.083 (2)	0.0516 (15)	−0.0001 (18)	−0.0152 (15)	0.0008 (14)
C17	0.0567 (15)	0.0551 (13)	0.0438 (12)	0.0038 (11)	0.0019 (11)	−0.0057 (10)
C18	0.0580 (15)	0.0545 (14)	0.0559 (15)	−0.0049 (11)	0.0013 (12)	−0.0167 (12)
C19	0.0575 (15)	0.0396 (11)	0.0632 (15)	−0.0071 (10)	0.0107 (12)	−0.0086 (11)
C20	0.0494 (12)	0.0386 (11)	0.0463 (12)	0.0021 (9)	0.0108 (10)	−0.0029 (9)

Geometric parameters (Å, º) top

O1—C6	1.333 (3)	C9—H9A	0.9700
O1—H1A	0.8200	C9—H9B	0.9700
O2—C20	1.345 (3)	C10—H10A	0.9700
O2—H2A	0.8200	C10—H10B	0.9700
N1—C8	1.274 (3)	C11—C12	1.530 (3)
N1—C9	1.467 (3)	C11—H11A	0.9700
N2—C13	1.277 (3)	C11—H11B	0.9700
N2—C12	1.461 (3)	C12—H12A	0.9700
N3—C11	1.453 (3)	C12—H12B	0.9700
N3—C10	1.456 (3)	C13—C14	1.461 (3)
N3—H3A	0.8600	C13—H13A	0.9300
C1—C3	1.386 (3)	C8—H8A	0.9300
C1—C7	1.394 (3)	C14—C15	1.401 (3)
C1—H1C	0.9300	C14—C20	1.411 (3)
C2—C3	1.505 (4)	C15—C17	1.386 (3)
C2—H2B	0.9600	C15—H15A	0.9300
C2—H2C	0.9600	C16—C17	1.521 (4)
C2—H2D	0.9600	C16—H16A	0.9600
C3—C4	1.395 (4)	C16—H16B	0.9600
C4—C5	1.375 (4)	C16—H16C	0.9600
C4—H4A	0.9300	C17—C18	1.400 (4)
C5—C6	1.397 (3)	C18—C19	1.383 (4)
C5—H5A	0.9300	C18—H18A	0.9300
C6—C7	1.424 (3)	C19—C20	1.396 (3)
C7—C8	1.453 (3)	C19—H19A	0.9300
C9—C10	1.524 (3)

C6—O1—H1A	109.5	N3—C11—C12	113.95 (19)
C20—O2—H2A	109.5	N3—C11—H11A	108.8
C8—N1—C9	120.3 (2)	C12—C11—H11A	108.8
C13—N2—C12	118.8 (2)	N3—C11—H11B	108.8
C11—N3—C10	115.3 (2)	C12—C11—H11B	108.8
C11—N3—H3A	122.3	H11A—C11—H11B	107.7
C10—N3—H3A	122.3	N2—C12—C11	109.28 (19)
C3—C1—C7	122.7 (2)	N2—C12—H12A	109.8
C3—C1—H1C	118.6	C11—C12—H12A	109.8
C7—C1—H1C	118.6	N2—C12—H12B	109.8
C3—C2—H2B	109.5	C11—C12—H12B	109.8
C3—C2—H2C	109.5	H12A—C12—H12B	108.3
H2B—C2—H2C	109.5	N2—C13—C14	121.6 (2)
C3—C2—H2D	109.5	N2—C13—H13A	119.2
H2B—C2—H2D	109.5	C14—C13—H13A	119.2
H2C—C2—H2D	109.5	N1—C8—C7	121.9 (2)
C1—C3—C4	117.2 (2)	N1—C8—H8A	119.0
C1—C3—C2	122.0 (2)	C7—C8—H8A	119.0
C4—C3—C2	120.9 (2)	C15—C14—C20	119.0 (2)
C5—C4—C3	122.3 (2)	C15—C14—C13	119.9 (2)
C5—C4—H4A	118.9	C20—C14—C13	121.0 (2)
C3—C4—H4A	118.9	C17—C15—C14	122.2 (2)
C4—C5—C6	120.5 (2)	C17—C15—H15A	118.9
C4—C5—H5A	119.7	C14—C15—H15A	118.9
C6—C5—H5A	119.7	C17—C16—H16A	109.5
O1—C6—C5	119.4 (2)	C17—C16—H16B	109.5
O1—C6—C7	122.0 (2)	H16A—C16—H16B	109.5
C5—C6—C7	118.6 (2)	C17—C16—H16C	109.5
C1—C7—C6	118.7 (2)	H16A—C16—H16C	109.5
C1—C7—C8	120.4 (2)	H16B—C16—H16C	109.5
C6—C7—C8	120.8 (2)	C15—C17—C18	117.5 (2)
N1—C9—C10	112.2 (2)	C15—C17—C16	120.9 (2)
N1—C9—H9A	109.2	C18—C17—C16	121.5 (3)
C10—C9—H9A	109.2	C19—C18—C17	121.8 (2)
N1—C9—H9B	109.2	C19—C18—H18A	119.1
C10—C9—H9B	109.2	C17—C18—H18A	119.1
H9A—C9—H9B	107.9	C18—C19—C20	120.3 (2)
N3—C10—C9	110.8 (2)	C18—C19—H19A	119.8
N3—C10—H10A	109.5	C20—C19—H19A	119.8
C9—C10—H10A	109.5	O2—C20—C19	119.1 (2)
N3—C10—H10B	109.5	O2—C20—C14	121.8 (2)
C9—C10—H10B	109.5	C19—C20—C14	119.1 (2)
H10A—C10—H10B	108.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.89	2.614 (4)	146
O2—H2A···N2	0.82	1.88	2.602 (3)	146
N3—H3A···O1ⁱ	0.86	2.54	3.140 (3)	128

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₅N₃O₂
M_r	339.43
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	296
a, b, c (Å)	9.132 (4), 5.834 (3), 34.365 (16)
V (Å³)	1830.8 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.34 × 0.32 × 0.28

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.970, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	14593, 2125, 1867
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.108, 1.07
No. of reflections	2125
No. of parameters	228
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.18

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), 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
O1—H1A···N1	0.82	1.89	2.614 (4)	146
O2—H2A···N2	0.82	1.88	2.602 (3)	146
N3—H3A···O1ⁱ	0.86	2.54	3.140 (3)	128

Symmetry code: (i) x, y−1, z.

Acknowledgements

We are grateful to the Starting Fund for the Doctoral Program of Xi'an University of Architecture & Technology (DB12051) for financial support.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Rodriguez de Barbarin, C. O., Bailey, N. A., Fenton, D. E. & He, Q. (1994). Inorg. Chim. Acta, 219, 205–207. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 7| July 2008| Page o1352

doi:10.1107/S1600536808018837

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

4,4′-Di­methyl-2,2′-[(3-aza­pentane-1,5-di­yl)bis­­(nitrilo­methyl­­idyne)]diphenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4,4′-Dimethyl-2,2′-[(3-azapentane-1,5-diyl)bis(nitrilomethylidyne)]diphenol