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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o166.
Published online 2007 December 6. doi:  10.1107/S1600536807064409
PMCID: PMC2915233

1-(2-Hydr­oxy-5-methoxy­phen­yl)ethan-1-one N-[(E)-1-(2-hydr­oxy-5-methoxy­phen­yl)ethyl­idene]hydrazone

Abstract

In the title mol­ecule, C18H20N2O4, which resides on a crystallographic centre of inversion (at the centre of the N—N bond), all non-H atoms apart from the meth­oxy substituent are approximately coplanar. The structure displays intra­molecular O—H(...)N hydrogen bonding.

Related literature

For related literature, see: Saroja et al. (1995 [triangle]); Sreerama et al. (2007 [triangle]); Sreerama & Pal (2005 [triangle]); Tian et al. (2007 [triangle]).

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Object name is e-64-0o166-scheme1.jpg

Experimental

Crystal data

  • C18H20N2O4
  • M r = 328.36
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o166-efi1.jpg
  • a = 8.5545 (7) Å
  • b = 6.4614 (4) Å
  • c = 14.3548 (10) Å
  • β = 91.243 (5)°
  • V = 793.26 (10) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 296 (2) K
  • 0.39 × 0.23 × 0.06 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (APEX2; Bruker, 2005 [triangle]) T min = 0.963, T max = 0.995
  • 7584 measured reflections
  • 1837 independent reflections
  • 1306 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.178
  • S = 1.05
  • 1837 reflections
  • 112 parameters
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807064409/gg2057sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064409/gg2057Isup2.hkl

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

Acknowledgments

This study was supported by the Natural Science Foundation of Shandong Province (grant No. Y2005B12).

supplementary crystallographic information

Comment

In bis Schiff base systems derived from hydrazine, the two chelating sites are connected directly by a single bond, (Saroja et al. 1995, Sreerama et al. 2005, 2007, Tian et al. 2007). However, To date, there has been no crystal structure report of the compound 2,2'-(1E,1'E)-1,1'-(hydrazine-1,2-diylidene)bis(ethan-1-yl-1-ylidene)bis(4-methoxyphenol). We report here the crystal structure of the title compound (Fig. 1).

In the title compound (Fig. 1), all bond lengths and angles are normal. Apart from the methoxy substituent, all non-H atoms of the molecule are coplanar to within 0.029 Å. In the crystal structure, intramolecular O—H···N hydrogen bonds are observed.

Experimental

A mixture of 1-(2-hydroxy-5-methoxyphenyl)ethanone (166 mg, 1 mmol), hydrazine sulfate (67 mg, 0.5 mmol) and triethylamine (153 mg, 1.5 mmol) in alcohol (10 ml) was heated to reflux for 32 h. After cooling, the precipitate was filtrated and washed with water to afford the product in 60% yield. Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid in ethyl acetate at room temperature for 10 d.

Refinement

All H atoms were placed in geometrically calculated positions and refined using a riding model with C—H = 0.97 Å (for CH2 groups) and 0.96 Å (for CH3 groups), their isotropic displacement parameters were set to 1.2 times (1.5 times for CH3 groups) the equivalent displacement parameter of their parent atoms.

Figures

Fig. 1.
The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
Fig. 2.
Packing view of (I), shown along the b axis direction.

Crystal data

C18H20N2O4F000 = 348
Mr = 328.36Dx = 1.375 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1667 reflections
a = 8.5545 (7) Åθ = 2.4–27.6º
b = 6.4614 (4) ŵ = 0.10 mm1
c = 14.3548 (10) ÅT = 296 (2) K
β = 91.243 (5)ºPlate, orange-yellow
V = 793.26 (10) Å30.39 × 0.23 × 0.06 mm
Z = 2

Data collection

Bruker APEXII CCD area-detector diffractometer1837 independent reflections
Radiation source: fine-focus sealed tube1306 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.023
T = 296(2) Kθmax = 27.6º
[var phi] and ω scansθmin = 2.4º
Absorption correction: multi-scan(APEX2; Bruker, 2005)h = −11→9
Tmin = 0.963, Tmax = 0.995k = −8→8
7584 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.178  w = 1/[σ2(Fo2) + (0.1017P)2 + 0.1301P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
1837 reflectionsΔρmax = 0.31 e Å3
112 parametersΔρmin = −0.25 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
C10.0145 (3)0.1588 (3)0.15985 (12)0.0546 (5)
H1A−0.06180.05000.15610.082*
H1B−0.03280.28150.18420.082*
H1C0.09960.11680.20030.082*
C20.0749 (2)0.2025 (2)0.06448 (11)0.0371 (4)
C30.17276 (19)0.3862 (2)0.04965 (11)0.0356 (4)
C40.2295 (2)0.4376 (3)−0.03962 (11)0.0413 (4)
C50.3199 (2)0.6135 (3)−0.05005 (13)0.0528 (5)
H50.35620.6473−0.10870.063*
C60.3574 (2)0.7398 (3)0.02449 (13)0.0500 (5)
H60.41850.85700.01590.060*
C70.3037 (2)0.6916 (3)0.11227 (12)0.0417 (4)
C80.2134 (2)0.5179 (3)0.12370 (11)0.0398 (4)
H80.17790.48680.18290.048*
C90.4389 (3)0.9765 (3)0.18430 (16)0.0620 (6)
H9A0.53890.92660.16500.093*
H9B0.45031.04300.24390.093*
H9C0.39891.07400.13930.093*
N10.04606 (16)0.0865 (2)−0.00768 (9)0.0394 (4)
O10.19804 (19)0.3216 (2)−0.11624 (9)0.0595 (5)
H10.14870.2184−0.10140.089*
O20.33331 (18)0.8075 (2)0.19129 (9)0.0572 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0789 (14)0.0512 (10)0.0339 (9)−0.0200 (9)0.0095 (9)0.0003 (8)
C20.0445 (10)0.0346 (8)0.0322 (8)−0.0006 (6)0.0023 (7)0.0020 (6)
C30.0387 (9)0.0346 (8)0.0334 (8)0.0006 (6)0.0017 (6)0.0019 (6)
C40.0461 (10)0.0440 (9)0.0340 (9)−0.0039 (7)0.0047 (7)−0.0005 (7)
C50.0597 (12)0.0576 (12)0.0415 (10)−0.0159 (9)0.0113 (8)0.0027 (8)
C60.0524 (12)0.0466 (10)0.0514 (11)−0.0145 (8)0.0065 (9)0.0038 (8)
C70.0463 (10)0.0363 (8)0.0423 (9)−0.0012 (7)−0.0017 (7)−0.0014 (7)
C80.0487 (10)0.0379 (8)0.0330 (8)−0.0020 (7)0.0031 (7)0.0005 (7)
C90.0744 (14)0.0471 (11)0.0641 (13)−0.0195 (10)−0.0072 (11)−0.0069 (9)
N10.0482 (9)0.0351 (7)0.0351 (7)−0.0052 (6)0.0049 (6)−0.0007 (6)
O10.0799 (11)0.0644 (9)0.0348 (7)−0.0262 (7)0.0129 (6)−0.0073 (6)
O20.0758 (10)0.0464 (7)0.0494 (8)−0.0202 (6)0.0028 (7)−0.0088 (6)

Geometric parameters (Å, °)

C1—C21.501 (2)C6—C71.386 (3)
C1—H1A0.9600C6—H60.9300
C1—H1B0.9600C7—C81.374 (2)
C1—H1C0.9600C7—O21.378 (2)
C2—N11.298 (2)C8—H80.9300
C2—C31.471 (2)C9—O21.422 (2)
C3—C81.400 (2)C9—H9A0.9600
C3—C41.420 (2)C9—H9B0.9600
C4—O11.353 (2)C9—H9C0.9600
C4—C51.385 (2)N1—N1i1.388 (3)
C5—C61.378 (3)O1—H10.8200
C5—H50.9300
C2—C1—H1A109.5C5—C6—C7119.81 (16)
C2—C1—H1B109.5C5—C6—H6120.1
H1A—C1—H1B109.5C7—C6—H6120.1
C2—C1—H1C109.5C8—C7—O2116.04 (15)
H1A—C1—H1C109.5C8—C7—C6119.35 (16)
H1B—C1—H1C109.5O2—C7—C6124.61 (16)
N1—C2—C3116.73 (14)C7—C8—C3122.47 (16)
N1—C2—C1123.78 (15)C7—C8—H8118.8
C3—C2—C1119.50 (15)C3—C8—H8118.8
C8—C3—C4117.32 (15)O2—C9—H9A109.5
C8—C3—C2120.91 (15)O2—C9—H9B109.5
C4—C3—C2121.77 (15)H9A—C9—H9B109.5
O1—C4—C5117.95 (15)O2—C9—H9C109.5
O1—C4—C3122.54 (15)H9A—C9—H9C109.5
C5—C4—C3119.51 (16)H9B—C9—H9C109.5
C6—C5—C4121.54 (17)C2—N1—N1i115.92 (16)
C6—C5—H5119.2C4—O1—H1109.5
C4—C5—H5119.2C7—O2—C9117.68 (16)
N1—C2—C3—C8−178.44 (15)C5—C6—C7—C80.0 (3)
C1—C2—C3—C81.5 (3)C5—C6—C7—O2−179.58 (17)
N1—C2—C3—C41.7 (2)O2—C7—C8—C3179.54 (15)
C1—C2—C3—C4−178.35 (17)C6—C7—C8—C30.0 (3)
C8—C3—C4—O1179.88 (15)C4—C3—C8—C70.3 (3)
C2—C3—C4—O1−0.2 (3)C2—C3—C8—C7−179.56 (15)
C8—C3—C4—C5−0.6 (3)C3—C2—N1—N1i179.83 (16)
C2—C3—C4—C5179.33 (16)C1—C2—N1—N1i−0.2 (3)
O1—C4—C5—C6−179.92 (18)C8—C7—O2—C9173.87 (16)
C3—C4—C5—C60.5 (3)C6—C7—O2—C9−6.6 (3)
C4—C5—C6—C7−0.2 (3)

Symmetry codes: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.832.5523 (18)146

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2057).

References

  • Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst.32, 115–119.
  • Bruker (1997). SHELXTL Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2005). APEX2 Version 2.0-2. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Saroja, J., Manivannan, V., Chakraborty, P. & Pal, S. (1995). Inorg. Chem.34, 3099–3101.
  • Sheldrick, G. M. (1997). SHELXL97 University of Göttingen, Germany. [PubMed]
  • Sreerama, S. G., Mukhopadhyay, A. & Pal, S. (2007). Polyhedron, 26, 4101–4106.
  • Sreerama, S. G. & Pal, S. (2005). Inorg. Chem.44, 6299–6307. [PubMed]
  • Tian, L., Hu, Z., Shi, P., Zhou, H., Wu, J., Tian, Y., Zhou, Y., Tao, X. & Jiang, M. (2007). J. Lumin.127, 423–430.

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