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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o646.
Published online 2009 February 28. doi:  10.1107/S1600536809003328
PMCID: PMC2968515

6,6′-Dieth­oxy-2,2′-[propane-1,2-diyl­bis(nitrilo­methyl­idyne)]diphenol

Abstract

In the title mol­ecule, C21H26N2O4, the dihedral angle between the two benzene rings is 88.4 (3)°. Two fairly strong intra­molecular O—H(...)N hydrogen bonds may, in part, influence the mol­ecular conformation.

Related literature

For background information on the coordination ability of tetradentate Schiff-base ligands, see: Bermejo et al. (2007 [triangle]); Ni et al. (2005 [triangle]); Nayak et al., 2006 [triangle]; Mohanta et al., 2002 [triangle]; Saha et al. (2007 [triangle]); Wang et al. (2008 [triangle]); Yu et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o646-scheme1.jpg

Experimental

Crystal data

  • C21H26N2O4
  • M r = 370.44
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o646-efi1.jpg
  • a = 9.140 (3) Å
  • b = 11.451 (4) Å
  • c = 13.013 (5) Å
  • α = 113.845 (5)°
  • β = 109.628 (6)°
  • γ = 108.812 (5)°
  • V = 993.5 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 273 (2) K
  • 0.12 × 0.11 × 0.09 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.990, T max = 0.992
  • 4894 measured reflections
  • 3451 independent reflections
  • 2325 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.193
  • S = 1.00
  • 3451 reflections
  • 249 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003328/lh2762sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003328/lh2762Isup2.hkl

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

supplementary crystallographic information

Comment

Among the tetradentate schiff-base ligands studied intensely during the past several decades, the planar, salen types and their complexes (with interesting magnetic properties) have been given much attention due to their excellent coordination ability, utilizing two N atoms and two O atoms (Ni et al., 2005; Wang et al., 2008; Yu et al., 2007; Nayak et al., 2006; Mohanta et al., 2002; Saha et al., 2007).

Herein, we report the synthesis and crystal structure of a new tetradentate Schiff base ligand, N,N'-bis(2-hydroxy-3-ethoxybenzylidene)- 1,2-diaminopropane. The molecular structure of the title compound is shown in Fig. 1. The molecule possesses an O2N2 donor set affording a potentially tetradentate ligand. The imide bond lengths 1.262 (3) for N1—C7 and 1.263 (3) Å for N2—C16 are slightly shorter than that of N,N'-bis(2-hydroxy-3-methoxybenzylidene)ethylenediamine (1.272 Å) (Bermejo, et al., 2007). The C—N bond distance of 1.461 (3) Å is in agreement well with that found in the same compound. Two fairly strong intramolecular O···H—N hydrogen bonds may in part influence the molecular conformation.

Experimental

The Schiff base ligand was synthesized by condensation 1,2-diaminopropane and 2-hydroxy-3-ethoxybenzaldehyde with molar ratio 1:2 in ethanol. The mixture formed was allowed to partially evaporate in air for sevral days to produce crystals suitable for X-ray diffraction with a yield about 65%.

Refinement

H atoms were placed in calculated positions with C—H distances of 0.93, 0.96, 0.97 Å and O—H 0.82 Å, and were allowed for as riding atoms with Uiso(H) = 1.5Ueq(C) for methyl H atoms, Uiso(H) = 1.2Ueq(C) for all other C bound H atoms and Uiso(H) = 1.2Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C21H26N2O4Z = 2
Mr = 370.44F(000) = 396
Triclinic, P1Dx = 1.238 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.140 (3) ÅCell parameters from 1361 reflections
b = 11.451 (4) Åθ = 2.4–23.9°
c = 13.013 (5) ŵ = 0.09 mm1
α = 113.845 (5)°T = 273 K
β = 109.628 (6)°Block, yellow
γ = 108.812 (5)°0.12 × 0.11 × 0.09 mm
V = 993.5 (6) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer3451 independent reflections
Radiation source: fine-focus sealed tube2325 reflections with I > 2σ(I)
graphiteRint = 0.030
[var phi] and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.990, Tmax = 0.992k = −13→11
4894 measured reflectionsl = −15→13

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.1202P)2] where P = (Fo2 + 2Fc2)/3
3451 reflections(Δ/σ)max < 0.001
249 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = −0.26 e Å3

Special details

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)

xyzUiso*/Ueq
O10.2732 (2)0.85334 (19)0.31097 (15)0.0615 (5)
H10.28810.88510.38480.092*
O20.1699 (2)0.75251 (19)0.06238 (15)0.0625 (5)
O30.1229 (2)0.44342 (19)0.38472 (16)0.0658 (5)
H30.16140.53360.43070.099*
O40.0549 (2)0.16836 (19)0.25933 (17)0.0666 (5)
N10.1898 (3)0.8527 (2)0.4813 (2)0.0553 (5)
N20.3270 (3)0.7183 (2)0.60118 (19)0.0571 (5)
C1−0.0337 (3)0.6987 (3)0.2479 (2)0.0521 (6)
C20.0950 (3)0.7499 (2)0.2166 (2)0.0477 (6)
C30.0365 (3)0.6931 (3)0.0830 (2)0.0514 (6)
C4−0.1454 (3)0.5848 (3)−0.0147 (3)0.0621 (7)
H4−0.18420.5446−0.10360.075*
C5−0.2713 (4)0.5348 (3)0.0171 (3)0.0717 (8)
H5−0.39370.4618−0.05040.086*
C6−0.2174 (3)0.5916 (3)0.1466 (3)0.0673 (7)
H6−0.30330.55880.16740.081*
C70.0251 (4)0.7553 (3)0.3859 (3)0.0554 (6)
H7−0.06190.71820.40450.067*
C80.1151 (4)0.6978 (3)−0.0732 (2)0.0642 (7)
H8A0.02690.7214−0.11030.077*
H8B0.05830.5892−0.12700.077*
C90.2824 (4)0.7724 (3)−0.0729 (3)0.0811 (9)
H9A0.33760.8797−0.01920.122*
H9B0.24920.7382−0.16260.122*
H9C0.36810.7475−0.03690.122*
C100.3713 (3)0.5196 (3)0.5889 (2)0.0523 (6)
C110.2296 (3)0.4113 (3)0.4549 (2)0.0509 (6)
C120.1958 (3)0.2656 (3)0.3898 (2)0.0543 (6)
C130.3036 (4)0.2294 (3)0.4590 (3)0.0641 (7)
H130.28160.13240.41610.077*
C140.4442 (4)0.3374 (3)0.5920 (3)0.0722 (8)
H140.51580.31240.63790.087*
C150.4778 (4)0.4803 (3)0.6557 (3)0.0687 (7)
H150.57280.55200.74460.082*
C160.4133 (3)0.6729 (3)0.6564 (2)0.0563 (6)
H160.50920.74180.74540.068*
C170.0096 (4)0.0166 (3)0.1890 (3)0.0718 (8)
H17A−0.0139−0.02730.23600.086*
H17B0.11000.01280.18100.086*
C18−0.1577 (5)−0.0678 (3)0.0545 (3)0.0911 (10)
H18A−0.2550−0.06080.06370.137*
H18B−0.1943−0.17170.00500.137*
H18C−0.1316−0.02530.00790.137*
C190.3894 (4)0.8780 (3)0.6768 (2)0.0609 (7)
H19A0.49580.93450.67790.073*
H19B0.42620.91450.76810.073*
C200.2425 (4)0.9054 (3)0.6181 (2)0.0606 (7)
H200.13540.84980.61810.073*
C210.3133 (5)1.0728 (3)0.6992 (3)0.0823 (9)
H21A0.41901.12740.70010.123*
H21B0.34641.10760.78890.123*
H21C0.21921.08910.65990.123*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0559 (10)0.0630 (11)0.0471 (9)0.0206 (9)0.0246 (9)0.0290 (9)
O20.0652 (11)0.0655 (11)0.0460 (9)0.0286 (9)0.0262 (8)0.0316 (9)
O30.0776 (12)0.0552 (11)0.0516 (10)0.0405 (10)0.0184 (9)0.0305 (9)
O40.0835 (12)0.0521 (10)0.0561 (11)0.0391 (10)0.0296 (10)0.0292 (9)
N10.0655 (13)0.0568 (12)0.0575 (12)0.0359 (11)0.0376 (11)0.0371 (11)
N20.0645 (12)0.0497 (12)0.0481 (12)0.0273 (10)0.0254 (10)0.0279 (10)
C10.0525 (13)0.0543 (14)0.0617 (15)0.0350 (12)0.0305 (12)0.0374 (13)
C20.0481 (13)0.0457 (13)0.0480 (13)0.0267 (11)0.0205 (11)0.0290 (11)
C30.0581 (14)0.0496 (14)0.0507 (14)0.0336 (12)0.0263 (12)0.0305 (12)
C40.0612 (16)0.0656 (17)0.0531 (15)0.0383 (14)0.0199 (13)0.0346 (13)
C50.0499 (15)0.0744 (19)0.0703 (19)0.0333 (14)0.0175 (14)0.0382 (16)
C60.0514 (15)0.0750 (18)0.0800 (19)0.0363 (14)0.0324 (15)0.0483 (16)
C70.0610 (15)0.0584 (15)0.0669 (16)0.0367 (13)0.0408 (14)0.0419 (14)
C80.0781 (17)0.0652 (16)0.0425 (13)0.0379 (14)0.0274 (13)0.0302 (13)
C90.095 (2)0.085 (2)0.0584 (17)0.0396 (18)0.0421 (16)0.0423 (16)
C100.0522 (13)0.0598 (15)0.0498 (13)0.0284 (12)0.0264 (12)0.0370 (12)
C110.0558 (13)0.0574 (15)0.0537 (14)0.0337 (12)0.0300 (12)0.0394 (12)
C120.0609 (15)0.0575 (15)0.0559 (15)0.0335 (13)0.0342 (13)0.0372 (13)
C130.0728 (17)0.0681 (17)0.0798 (19)0.0450 (15)0.0460 (16)0.0538 (16)
C140.0699 (17)0.083 (2)0.083 (2)0.0471 (16)0.0342 (16)0.0630 (18)
C150.0634 (16)0.0759 (19)0.0646 (16)0.0350 (15)0.0245 (14)0.0484 (15)
C160.0538 (14)0.0562 (15)0.0439 (13)0.0209 (12)0.0201 (12)0.0291 (12)
C170.0860 (19)0.0567 (17)0.079 (2)0.0429 (16)0.0472 (17)0.0374 (15)
C180.106 (2)0.0601 (18)0.080 (2)0.0436 (18)0.041 (2)0.0271 (17)
C190.0686 (15)0.0513 (15)0.0475 (14)0.0251 (13)0.0255 (12)0.0271 (12)
C200.0739 (17)0.0623 (16)0.0578 (15)0.0367 (14)0.0445 (14)0.0359 (13)
C210.114 (2)0.0701 (19)0.081 (2)0.0571 (19)0.063 (2)0.0424 (17)

Geometric parameters (Å, °)

O1—C21.341 (3)C9—H9B0.9600
O1—H10.8200C9—H9C0.9600
O2—C31.361 (3)C10—C151.391 (3)
O2—C81.437 (3)C10—C111.397 (3)
O3—C111.351 (3)C10—C161.447 (3)
O3—H30.8200C11—C121.394 (3)
O4—C121.364 (3)C12—C131.387 (4)
O4—C171.423 (3)C13—C141.388 (4)
N1—C71.262 (3)C13—H130.9300
N1—C201.461 (3)C14—C151.366 (4)
N2—C161.263 (3)C14—H140.9300
N2—C191.461 (3)C15—H150.9300
C1—C61.393 (3)C16—H160.9300
C1—C21.401 (3)C17—C181.489 (4)
C1—C71.456 (4)C17—H17A0.9700
C2—C31.404 (3)C17—H17B0.9700
C3—C41.376 (3)C18—H18A0.9600
C4—C51.382 (4)C18—H18B0.9600
C4—H40.9300C18—H18C0.9600
C5—C61.362 (4)C19—C201.503 (4)
C5—H50.9300C19—H19A0.9700
C6—H60.9300C19—H19B0.9700
C7—H70.9300C20—C211.521 (4)
C8—C91.490 (4)C20—H200.9800
C8—H8A0.9700C21—H21A0.9600
C8—H8B0.9700C21—H21B0.9600
C9—H9A0.9600C21—H21C0.9600
C2—O1—H1109.5O4—C12—C13124.9 (2)
C3—O2—C8116.92 (19)O4—C12—C11115.6 (2)
C11—O3—H3109.5C13—C12—C11119.5 (2)
C12—O4—C17118.2 (2)C12—C13—C14120.2 (3)
C7—N1—C20120.5 (2)C12—C13—H13119.9
C16—N2—C19118.7 (2)C14—C13—H13119.9
C6—C1—C2119.9 (2)C15—C14—C13120.3 (2)
C6—C1—C7120.0 (2)C15—C14—H14119.9
C2—C1—C7120.1 (2)C13—C14—H14119.9
O1—C2—C1122.0 (2)C14—C15—C10120.7 (3)
O1—C2—C3118.7 (2)C14—C15—H15119.6
C1—C2—C3119.4 (2)C10—C15—H15119.6
O2—C3—C4125.7 (2)N2—C16—C10123.6 (2)
O2—C3—C2115.3 (2)N2—C16—H16118.2
C4—C3—C2119.1 (2)C10—C16—H16118.2
C3—C4—C5121.1 (2)O4—C17—C18107.3 (2)
C3—C4—H4119.4O4—C17—H17A110.3
C5—C4—H4119.4C18—C17—H17A110.3
C6—C5—C4120.5 (2)O4—C17—H17B110.3
C6—C5—H5119.8C18—C17—H17B110.3
C4—C5—H5119.8H17A—C17—H17B108.5
C5—C6—C1120.0 (3)C17—C18—H18A109.5
C5—C6—H6120.0C17—C18—H18B109.5
C1—C6—H6120.0H18A—C18—H18B109.5
N1—C7—C1122.4 (2)C17—C18—H18C109.5
N1—C7—H7118.8H18A—C18—H18C109.5
C1—C7—H7118.8H18B—C18—H18C109.5
O2—C8—C9107.9 (2)N2—C19—C20112.0 (2)
O2—C8—H8A110.1N2—C19—H19A109.2
C9—C8—H8A110.1C20—C19—H19A109.2
O2—C8—H8B110.1N2—C19—H19B109.2
C9—C8—H8B110.1C20—C19—H19B109.2
H8A—C8—H8B108.4H19A—C19—H19B107.9
C8—C9—H9A109.5N1—C20—C19109.1 (2)
C8—C9—H9B109.5N1—C20—C21109.2 (2)
H9A—C9—H9B109.5C19—C20—C21110.2 (2)
C8—C9—H9C109.5N1—C20—H20109.5
H9A—C9—H9C109.5C19—C20—H20109.5
H9B—C9—H9C109.5C21—C20—H20109.5
C15—C10—C11119.3 (2)C20—C21—H21A109.5
C15—C10—C16119.9 (2)C20—C21—H21B109.5
C11—C10—C16120.8 (2)H21A—C21—H21B109.5
O3—C11—C12118.1 (2)C20—C21—H21C109.5
O3—C11—C10121.8 (2)H21A—C21—H21C109.5
C12—C11—C10120.0 (2)H21B—C21—H21C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···N20.821.892.614 (3)147
O1—H1···N10.821.852.576 (2)146

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2762).

References

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Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography