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

Zhang, J.-H.; Dong, W.-L.; Ge, Y.-Q.; Zhao, B.-X.

doi:10.1107/S1600536807064409

organic compounds

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

Jin-Hua Zhang,^a Wen-Liang Dong,^b Yan-Qing Ge ^a and Bao-Xiang Zhao ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China, and ^bShandong University of Traditional Chinese Medicine, Jinan 250355, People's Republic of China
^*Correspondence e-mail: sduzhao@hotmail.com

(Received 20 November 2007; accepted 29 November 2007; online 6 December 2007)

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 ); Sreerama et al. (2007 ); Sreerama & Pal (2005 ); Tian et al. (2007 ).

Experimental

Crystal data

C₁₈H₂₀N₂O₄
M_r = 328.36
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.178
S = 1.05
1837 reflections
112 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.83	2.5523 (18)	146

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

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064409/gg2057Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

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

Figures top

	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.

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

Crystal data top

C₁₈H₂₀N₂O₄	F(000) = 348
M_r = 328.36	D_x = 1.375 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1667 reflections
a = 8.5545 (7) Å	θ = 2.4–27.6°
b = 6.4614 (4) Å	µ = 0.10 mm⁻¹
c = 14.3548 (10) Å	T = 296 K
β = 91.243 (5)°	Plate, orange-yellow
V = 793.26 (10) Å³	0.39 × 0.23 × 0.06 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	1837 independent reflections
Radiation source: fine-focus sealed tube	1306 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
φ and ω scans	θ_max = 27.6°, θ_min = 2.4°
Absorption correction: multi-scan (APEX2; Bruker, 2005)	h = −11→9
T_min = 0.963, T_max = 0.995	k = −8→8
7584 measured reflections	l = −18→18

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.178	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1017P)² + 0.1301P] where P = (F_o² + 2F_c²)/3
1837 reflections	(Δ/σ)_max = 0.001
112 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₈H₂₀N₂O₄	V = 793.26 (10) Å³
M_r = 328.36	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.5545 (7) Å	µ = 0.10 mm⁻¹
b = 6.4614 (4) Å	T = 296 K
c = 14.3548 (10) Å	0.39 × 0.23 × 0.06 mm
β = 91.243 (5)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1837 independent reflections
Absorption correction: multi-scan (APEX2; Bruker, 2005)	1306 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.995	R_int = 0.023
7584 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 1.05	Δρ_max = 0.31 e Å⁻³
1837 reflections	Δρ_min = −0.25 e Å⁻³
112 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
C1	0.0145 (3)	0.1588 (3)	0.15985 (12)	0.0546 (5)
H1A	−0.0618	0.0500	0.1561	0.082*
H1B	−0.0328	0.2815	0.1842	0.082*
H1C	0.0996	0.1168	0.2003	0.082*
C2	0.0749 (2)	0.2025 (2)	0.06448 (11)	0.0371 (4)
C3	0.17276 (19)	0.3862 (2)	0.04965 (11)	0.0356 (4)
C4	0.2295 (2)	0.4376 (3)	−0.03962 (11)	0.0413 (4)
C5	0.3199 (2)	0.6135 (3)	−0.05005 (13)	0.0528 (5)
H5	0.3562	0.6473	−0.1087	0.063*
C6	0.3574 (2)	0.7398 (3)	0.02449 (13)	0.0500 (5)
H6	0.4185	0.8570	0.0159	0.060*
C7	0.3037 (2)	0.6916 (3)	0.11227 (12)	0.0417 (4)
C8	0.2134 (2)	0.5179 (3)	0.12370 (11)	0.0398 (4)
H8	0.1779	0.4868	0.1829	0.048*
C9	0.4389 (3)	0.9765 (3)	0.18430 (16)	0.0620 (6)
H9A	0.5389	0.9266	0.1650	0.093*
H9B	0.4503	1.0430	0.2439	0.093*
H9C	0.3989	1.0740	0.1393	0.093*
N1	0.04606 (16)	0.0865 (2)	−0.00768 (9)	0.0394 (4)
O1	0.19804 (19)	0.3216 (2)	−0.11624 (9)	0.0595 (5)
H1	0.1487	0.2184	−0.1014	0.089*
O2	0.33331 (18)	0.8075 (2)	0.19129 (9)	0.0572 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0789 (14)	0.0512 (10)	0.0339 (9)	−0.0200 (9)	0.0095 (9)	0.0003 (8)
C2	0.0445 (10)	0.0346 (8)	0.0322 (8)	−0.0006 (6)	0.0023 (7)	0.0020 (6)
C3	0.0387 (9)	0.0346 (8)	0.0334 (8)	0.0006 (6)	0.0017 (6)	0.0019 (6)
C4	0.0461 (10)	0.0440 (9)	0.0340 (9)	−0.0039 (7)	0.0047 (7)	−0.0005 (7)
C5	0.0597 (12)	0.0576 (12)	0.0415 (10)	−0.0159 (9)	0.0113 (8)	0.0027 (8)
C6	0.0524 (12)	0.0466 (10)	0.0514 (11)	−0.0145 (8)	0.0065 (9)	0.0038 (8)
C7	0.0463 (10)	0.0363 (8)	0.0423 (9)	−0.0012 (7)	−0.0017 (7)	−0.0014 (7)
C8	0.0487 (10)	0.0379 (8)	0.0330 (8)	−0.0020 (7)	0.0031 (7)	0.0005 (7)
C9	0.0744 (14)	0.0471 (11)	0.0641 (13)	−0.0195 (10)	−0.0072 (11)	−0.0069 (9)
N1	0.0482 (9)	0.0351 (7)	0.0351 (7)	−0.0052 (6)	0.0049 (6)	−0.0007 (6)
O1	0.0799 (11)	0.0644 (9)	0.0348 (7)	−0.0262 (7)	0.0129 (6)	−0.0073 (6)
O2	0.0758 (10)	0.0464 (7)	0.0494 (8)	−0.0202 (6)	0.0028 (7)	−0.0088 (6)

Geometric parameters (Å, º) top

C1—C2	1.501 (2)	C6—C7	1.386 (3)
C1—H1A	0.9600	C6—H6	0.9300
C1—H1B	0.9600	C7—C8	1.374 (2)
C1—H1C	0.9600	C7—O2	1.378 (2)
C2—N1	1.298 (2)	C8—H8	0.9300
C2—C3	1.471 (2)	C9—O2	1.422 (2)
C3—C8	1.400 (2)	C9—H9A	0.9600
C3—C4	1.420 (2)	C9—H9B	0.9600
C4—O1	1.353 (2)	C9—H9C	0.9600
C4—C5	1.385 (2)	N1—N1ⁱ	1.388 (3)
C5—C6	1.378 (3)	O1—H1	0.8200
C5—H5	0.9300

C2—C1—H1A	109.5	C5—C6—C7	119.81 (16)
C2—C1—H1B	109.5	C5—C6—H6	120.1
H1A—C1—H1B	109.5	C7—C6—H6	120.1
C2—C1—H1C	109.5	C8—C7—O2	116.04 (15)
H1A—C1—H1C	109.5	C8—C7—C6	119.35 (16)
H1B—C1—H1C	109.5	O2—C7—C6	124.61 (16)
N1—C2—C3	116.73 (14)	C7—C8—C3	122.47 (16)
N1—C2—C1	123.78 (15)	C7—C8—H8	118.8
C3—C2—C1	119.50 (15)	C3—C8—H8	118.8
C8—C3—C4	117.32 (15)	O2—C9—H9A	109.5
C8—C3—C2	120.91 (15)	O2—C9—H9B	109.5
C4—C3—C2	121.77 (15)	H9A—C9—H9B	109.5
O1—C4—C5	117.95 (15)	O2—C9—H9C	109.5
O1—C4—C3	122.54 (15)	H9A—C9—H9C	109.5
C5—C4—C3	119.51 (16)	H9B—C9—H9C	109.5
C6—C5—C4	121.54 (17)	C2—N1—N1ⁱ	115.92 (16)
C6—C5—H5	119.2	C4—O1—H1	109.5
C4—C5—H5	119.2	C7—O2—C9	117.68 (16)

N1—C2—C3—C8	−178.44 (15)	C5—C6—C7—C8	0.0 (3)
C1—C2—C3—C8	1.5 (3)	C5—C6—C7—O2	−179.58 (17)
N1—C2—C3—C4	1.7 (2)	O2—C7—C8—C3	179.54 (15)
C1—C2—C3—C4	−178.35 (17)	C6—C7—C8—C3	0.0 (3)
C8—C3—C4—O1	179.88 (15)	C4—C3—C8—C7	0.3 (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—N1ⁱ	179.83 (16)
C2—C3—C4—C5	179.33 (16)	C1—C2—N1—N1ⁱ	−0.2 (3)
O1—C4—C5—C6	−179.92 (18)	C8—C7—O2—C9	173.87 (16)
C3—C4—C5—C6	0.5 (3)	C6—C7—O2—C9	−6.6 (3)
C4—C5—C6—C7	−0.2 (3)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.83	2.5523 (18)	146

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O₄
M_r	328.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.5545 (7), 6.4614 (4), 14.3548 (10)
β (°)	91.243 (5)
V (Å³)	793.26 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.39 × 0.23 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (APEX2; Bruker, 2005)
T_min, T_max	0.963, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	7584, 1837, 1306
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.178, 1.05
No. of reflections	1837
No. of parameters	112
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.25

Computer programs: APEX2 (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.83	2.5523 (18)	146

Acknowledgements

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

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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (1997). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Version 2.0-2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Saroja, J., Manivannan, V., Chakraborty, P. & Pal, S. (1995). Inorg. Chem. 34, 3099–3101. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany. Google Scholar
Sreerama, S. G., Mukhopadhyay, A. & Pal, S. (2007). Polyhedron, 26, 4101–4106. Web of Science CSD CrossRef CAS Google Scholar
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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

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https://doi.org/10.1107/S1600536807064409

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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