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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3151.
Published online 2009 November 21. doi:  10.1107/S1600536809048831
PMCID: PMC2971760

2,2′-[Ethyl­enebis(azanediyl­methyl­ene)]diphenol

Abstract

In the title compound, C16H20N2O4, the mol­ecule features a zigzag –CH2–NH–CH2–CH2–NH–CH2– chain whose ends are connected to the hydroxy­phenyl rings. The mol­ecules lies about a center of inversion. The imino group is a hydrogen-bond donor for the hydr­oxy group, which is a hydrogen-bond donor for the imino group of an adjacent mol­ecule. This latter inter­molecular hydrogen bonding leads to a layer structure.

Related literature

The title compound was doubly-deprotonated, forming several tetra­dentate chelated metal complexes. For their crystal structures, see: Atwood et al. (1995 [triangle], 1996 [triangle]); Borer et al. (1983 [triangle]); Bottcher et al. (1994 [triangle]); García-Zarracino et al. (2002 [triangle]); Henrick et al. (1984 [triangle]); Viswanathan et al. (1998 [triangle]); Xie et al. (2006 [triangle]); Yang et al. (2007 [triangle]).

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Object name is e-65-o3151-scheme1.jpg

Experimental

Crystal data

  • C16H20N2O2
  • M r = 272.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3151-efi1.jpg
  • a = 15.263 (2) Å
  • b = 4.860 (1) Å
  • c = 9.770 (1) Å
  • β = 96.318 (3)°
  • V = 720.3 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.31 × 0.27 × 0.25 mm

Data collection

  • Rigaku R-AXIS RAPID IP diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.975, T max = 0.979
  • 6726 measured reflections
  • 1635 independent reflections
  • 912 reflections with I > 2σ(I)
  • R int = 0.055

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.176
  • S = 1.09
  • 1635 reflections
  • 99 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048831/xu2679sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048831/xu2679Isup2.hkl

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

Acknowledgments

We thank the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Scientific Fund of Remarkable Teachers of Heilongjiang Province (No. 1054 G036), Heilongjiang University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

To a solution of salicylaldehyde (2.44 g, 20 mmol) in methanol was added a solution of ethylenediamine (0.6 ml, 10 mmol) in methanol. The solution was heated for two hours. The yellow Schiff base that was isolated upon evaporation of the solvent was reduced in absolute methanol by sodium borohydride. Colorless prismatic crystals were grown from a solution of the diamine in methanol.

Refinement

Carbon-bound H-atoms generated geometrically (0.93–0.97 Å, Uiso(H) = 1.2Ueq(C)). The nitrogen- and oxygen-bound H-atoms were refined with a distance restraint of N–H = O–H = 0.85±0.01 Å; their temperature factors were refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the molecule of C16H20N2O2 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C16H20N2O2F(000) = 292
Mr = 272.34Dx = 1.256 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3415 reflections
a = 15.263 (2) Åθ = 4.0–27.4°
b = 4.860 (1) ŵ = 0.08 mm1
c = 9.770 (1) ÅT = 293 K
β = 96.318 (3)°Prism, colorless
V = 720.3 (2) Å30.31 × 0.27 × 0.25 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID IP diffractometer1635 independent reflections
Radiation source: fine-focus sealed tube912 reflections with I > 2σ(I)
graphiteRint = 0.055
ω scanθmax = 27.4°, θmin = 4.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −19→19
Tmin = 0.975, Tmax = 0.979k = −6→6
6726 measured reflectionsl = −12→11

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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176H atoms treated by a mixture of independent and constrained refinement
S = 1.09w = 1/[σ2(Fo2) + (0.0749P)2 + 0.1302P] where P = (Fo2 + 2Fc2)/3
1635 reflections(Δ/σ)max = 0.001
99 parametersΔρmax = 0.21 e Å3
2 restraintsΔρmin = −0.19 e Å3

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

xyzUiso*/Ueq
O10.34270 (10)0.3118 (4)0.13029 (16)0.0555 (5)
N10.38397 (11)0.4899 (4)0.41165 (18)0.0451 (5)
C10.25836 (14)0.3821 (5)0.1507 (2)0.0439 (6)
C20.18572 (15)0.2708 (5)0.0744 (2)0.0552 (6)
H2A0.19320.14040.00700.066*
C30.10190 (15)0.3510 (6)0.0972 (3)0.0622 (7)
H30.05320.27320.04600.075*
C40.09036 (16)0.5466 (6)0.1958 (3)0.0624 (7)
H40.03400.60400.21030.075*
C50.16325 (16)0.6564 (5)0.2727 (2)0.0564 (7)
H50.15520.78710.33970.068*
C60.24808 (13)0.5773 (5)0.2530 (2)0.0443 (6)
C70.32748 (15)0.6983 (5)0.3364 (2)0.0524 (6)
H7A0.36210.79870.27540.063*
H7B0.30790.82850.40190.063*
C80.46843 (13)0.6100 (5)0.4701 (2)0.0497 (6)
H8A0.45790.74030.54180.060*
H8B0.49470.70910.39880.060*
H1O0.3458 (18)0.209 (5)0.0600 (19)0.081 (10)*
H1N0.3943 (15)0.370 (4)0.3504 (19)0.060 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0458 (10)0.0730 (13)0.0477 (10)0.0062 (8)0.0060 (7)−0.0106 (8)
N10.0441 (10)0.0469 (12)0.0432 (10)−0.0043 (8)0.0005 (8)−0.0013 (9)
C10.0434 (12)0.0475 (13)0.0409 (11)0.0033 (10)0.0055 (9)0.0053 (10)
C20.0546 (14)0.0616 (16)0.0482 (13)−0.0008 (11)−0.0005 (11)−0.0064 (12)
C30.0457 (14)0.0746 (19)0.0642 (16)−0.0037 (12)−0.0036 (12)0.0023 (14)
C40.0465 (13)0.0746 (19)0.0660 (16)0.0126 (13)0.0065 (12)0.0082 (14)
C50.0565 (14)0.0592 (16)0.0536 (14)0.0127 (12)0.0074 (11)0.0000 (11)
C60.0489 (13)0.0424 (13)0.0418 (11)0.0012 (9)0.0050 (10)0.0039 (9)
C70.0570 (14)0.0458 (14)0.0532 (13)0.0055 (11)0.0014 (11)0.0000 (11)
C80.0480 (13)0.0493 (15)0.0510 (13)−0.0079 (10)0.0009 (10)−0.0009 (11)

Geometric parameters (Å, °)

O1—C11.367 (2)C4—C51.380 (4)
O1—H1O0.86 (1)C4—H40.9300
N1—C81.472 (3)C5—C61.384 (3)
N1—C71.473 (3)C5—H50.9300
N1—H1N0.86 (1)C6—C71.504 (3)
C1—C21.377 (3)C7—H7A0.9700
C1—C61.399 (3)C7—H7B0.9700
C2—C31.379 (3)C8—C8i1.513 (4)
C2—H2A0.9300C8—H8A0.9700
C3—C41.379 (4)C8—H8B0.9700
C3—H30.9300
C1—O1—H1O113.5 (19)C4—C5—H5119.1
C8—N1—C7111.12 (17)C6—C5—H5119.1
C8—N1—H1N108.6 (16)C5—C6—C1117.9 (2)
C7—N1—H1N105.1 (16)C5—C6—C7121.7 (2)
O1—C1—C2122.6 (2)C1—C6—C7120.34 (19)
O1—C1—C6117.04 (19)N1—C7—C6113.21 (18)
C2—C1—C6120.4 (2)N1—C7—H7A108.9
C1—C2—C3120.5 (2)C6—C7—H7A108.9
C1—C2—H2A119.7N1—C7—H7B108.9
C3—C2—H2A119.7C6—C7—H7B108.9
C2—C3—C4120.0 (2)H7A—C7—H7B107.8
C2—C3—H3120.0N1—C8—C8i111.3 (2)
C4—C3—H3120.0N1—C8—H8A109.4
C3—C4—C5119.4 (2)C8i—C8—H8A109.4
C3—C4—H4120.3N1—C8—H8B109.4
C5—C4—H4120.3C8i—C8—H8B109.4
C4—C5—C6121.8 (2)H8A—C8—H8B108.0
O1—C1—C2—C3−179.0 (2)C2—C1—C6—C5−1.0 (3)
C6—C1—C2—C30.4 (4)O1—C1—C6—C7−0.7 (3)
C1—C2—C3—C40.8 (4)C2—C1—C6—C7179.9 (2)
C2—C3—C4—C5−1.2 (4)C8—N1—C7—C6169.35 (18)
C3—C4—C5—C60.6 (4)C5—C6—C7—N1122.4 (2)
C4—C5—C6—C10.6 (4)C1—C6—C7—N1−58.5 (3)
C4—C5—C6—C7179.7 (2)C7—N1—C8—C8i−171.9 (2)
O1—C1—C6—C5178.39 (19)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1o···N1ii0.86 (1)1.89 (1)2.721 (2)165 (3)
N1—H1n···O10.86 (1)2.23 (2)2.884 (2)133 (2)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2679).

References

  • Atwood, D. A., Jegier, J. A., Lindholm, N. F., Martin, K. J. & Rutherford, D. R. (1996). J. Coord. Chem. 38, 305–318.
  • Atwood, D. A., Jegier, J. A., Martin, K. J. & Rutherford, D. (1995). J. Organomet. Chem. 503, C4–C7.
  • Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
  • Borer, L., Thalken, L., Ceccarelli, C., Glick, M., Zhang, J. H. & Reiff, W. M. (1983). Inorg. Chem. 22, 1719–1724.
  • Bottcher, A., Elias, H., Glerup, J., Neuburger, M., Olsen, C. E., Paulus, H., Sprinbborg, J. & Zehinder, M. (1994). Acta Chem. Scand. 48, 967–980.
  • García-Zarracino, R., Ramos-Quiñones, J. & Höpfl, H. (2002). J. Organomet. Chem. 664, 188–200.
  • Henrick, K., Lindoy, L. F., McPartlin, M., Tasker, P. A. & Wood, M. P. (1984). J. Am. Chem. Soc. 106, 1641–1645.
  • Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
  • Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Viswanathan, R., Palaniandavar, M., Prabakaran, P. & Muthiah, P. T. (1998). Inorg. Chem. 37, 3881–3884. [PubMed]
  • Westrip, S. P. (2009). publCIF. In preparation.
  • Xie, Y.-S., Liu, Q.-L., Jiang, H., Ni, J., Hui, J. & Jia, N. (2006). Eur. J. Inorg. Chem. pp. 4010–4016.
  • Yang, S.-P., Han, L.-J., Wang, D.-Q. & Wang, B. (2007). Acta Cryst. E63, m2777–m2778.

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