2-[({2-[(2-Hy­droxy-5-meth­oxy­benzyl­idene)amino]­eth­yl}imino)­meth­yl]-4-meth­oxy­phenol

Ourari, A.; Baameur, L.; Bouacida, S.; Ouari, K.

doi:10.1107/S1600536812018405

organic compounds

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Volume 68| Part 6| June 2012| Page o1760

doi:10.1107/S1600536812018405

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2-[({2-[(2-Hydroxy-5-methoxybenzylidene)amino]ethyl}imino)methyl]-4-methoxyphenol

Ali Ourari,^a Lotfi Baameur,^a Sofiane Bouacida ^b ^* and Kamel Ouari ^a

^aLaboratoire d'Electrochimie, d'Ingénierie Moléculaire et de Catalyse Redox (LEIMCR), Faculté des Sciences de l'Ingénieur, Université Farhat Abbas, Sétif 19000, Algeria, and ^bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Université Mentouri-Constantine, 25000 Algeria
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 23 April 2012; accepted 24 April 2012; online 16 May 2012)

The asymmetric unit of the title compound, C₁₈H₂₀N₂O₄, contains one-half molecule with an inversion center located at the centroid of the molecule. In the crystal, molecules are linked by C—H⋯π interactions, forming layers parallel to (101). An intramolecular O—H⋯N hydrogen bond also occurs.

Related literature

For the synthesis of similar compounds see: Srinivasan et al. (1986 ); Moutet & Ourari (1997 ); Ourari et al. (2008 ).

Experimental

Crystal data

C₁₈H₂₀N₂O₄
M_r = 328.36
Monoclinic, P 2₁ /c
a = 15.0040 (12) Å
b = 5.9722 (3) Å
c = 9.3128 (8) Å
β = 92.001 (3)°
V = 833.98 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.50 × 0.23 × 0.19 mm

Data collection

Nonius KappaCCD diffractometer
3001 measured reflections
1664 independent reflections
1097 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.167
S = 1.05
1664 reflections
111 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯N2	0.82	1.85	2.5844 (18)	148
C10—H10C⋯Cgⁱ	0.96	2.64	3.521 (2)	152
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and DIAMOND (Brandenburg & Berndt, 2001 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812018405/bq2353sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018405/bq2353Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812018405/bq2353Isup3.cml

checkCIF report

Comment top

The tetradentate Schiff base ligands derived from salicylaldehyde derivatives and diamino compounds have been found to be excellent chelating agents for most applications in coordination chemistry such as in catalysis (Srinivasan et al., 1986) and electrocatalysis (Moutet & Ourari, 1997; Ourari et al., 2008). Here, we report the synthesis of the title compound and its crystal structure.

The molecular structure of (I), and the atomic numbering used, is illustrated in Fig. 1. The asymmetric unit of the title compound, consists of one-half of the molecule, with the other half generated by a crystallographic inversion center. The crystal packing in the title structure can be described by a zigzag layers parallel to (101) plane (Fig. 2). There is one intramolecular O—H···N hydrogen bonding in this packing (Table 1, Fig. 2), which it is stabilized C—H···π and Van der Walls interactions (table 1) All these interactions link the molecules within the layers and also link the layers together and reinforcing the cohesion of the structure.

Related literature top

For the synthesis of similar compounds see: Srinivasan et al. (1986); Moutet & Ourari (1997); Ourari et al. (2008).

Experimental top

60 mg of 1,2-diaminoethane (1 mmol) were dissolved in 10 ml of absolute ethanol. This solution was drop wise added, under stirring, to an ethanolic solution (10 ml) containing 304 mg of 5-methoxysalicylaldehyde (2 mmol). This mixture was refluxed for 1 h after which a yellow precipitate is formed, recovered by filtration, washed several times with diethyl oxide and dried to yield 282 mg (86%) of the title compound. The suitable crystals for X-ray analysis were obtained by slow evaporation from a mixture of solvents ethanol/dichloromethane (8/2, v/v).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular geometry of (I) with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. Only the contents of the asymmetric unit are numbered.
	Fig. 2. Diagram of layered packing parallel to (101) plane and showing O—H···N and C—H···π interactions.

2-[({2-[(2-Hydroxy-5-methoxybenzylidene)amino]ethyl}imino)methyl]- 4-methoxyphenol top

Crystal data top

C₁₈H₂₀N₂O₄	F(000) = 348
M_r = 328.36	D_x = 1.308 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1761 reflections
a = 15.0040 (12) Å	θ = 1.0–26.4°
b = 5.9722 (3) Å	µ = 0.09 mm⁻¹
c = 9.3128 (8) Å	T = 295 K
β = 92.001 (3)°	Prism, colorless
V = 833.98 (11) Å³	0.50 × 0.23 × 0.19 mm
Z = 2

Data collection top

Nonius KappaCCD diffractometer	1097 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	R_int = 0.021
Graphite monochromator	θ_max = 26.4°, θ_min = 2.7°
Detector resolution: 9 pixels mm^-1	h = −18→18
CCD rotation images, thick slices scans	k = −6→7
3001 measured reflections	l = −11→11
1664 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.167	w = 1/[σ²(F_o²) + (0.101P)² + 0.0006P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
1664 reflections	Δρ_max = 0.23 e Å⁻³
111 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.08 (2)

Crystal data top

C₁₈H₂₀N₂O₄	V = 833.98 (11) Å³
M_r = 328.36	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.0040 (12) Å	µ = 0.09 mm⁻¹
b = 5.9722 (3) Å	T = 295 K
c = 9.3128 (8) Å	0.50 × 0.23 × 0.19 mm
β = 92.001 (3)°

Data collection top

Nonius KappaCCD diffractometer	1097 reflections with I > 2σ(I)
3001 measured reflections	R_int = 0.021
1664 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.05	Δρ_max = 0.23 e Å⁻³
1664 reflections	Δρ_min = −0.16 e Å⁻³
111 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	0.00544 (12)	0.5332 (3)	0.42227 (18)	0.0554 (5)
H1A	0.0237	0.404	0.3674	0.066*
H1B	−0.0511	0.586	0.3816	0.066*
C3	0.13689 (11)	0.6835 (3)	0.32973 (18)	0.0500 (5)
H3	0.1399	0.5537	0.2749	0.06*
C4	0.20642 (11)	0.8520 (3)	0.31789 (17)	0.0488 (5)
C5	0.20521 (13)	1.0483 (3)	0.40154 (19)	0.0545 (5)
C6	0.27360 (14)	1.2037 (3)	0.3894 (2)	0.0620 (5)
H6	0.2731	1.3341	0.4439	0.074*
C7	0.34154 (14)	1.1672 (3)	0.2983 (2)	0.0623 (5)
H7	0.3863	1.2739	0.2909	0.075*
C8	0.34469 (12)	0.9719 (3)	0.21605 (18)	0.0542 (5)
C9	0.27715 (11)	0.8166 (3)	0.22553 (18)	0.0515 (5)
H9	0.2784	0.687	0.1702	0.062*
C10	0.42592 (14)	0.7497 (3)	0.0532 (3)	0.0764 (7)
H10A	0.4313	0.6263	0.119	0.115*
H10B	0.4781	0.7572	−0.0033	0.115*
H10C	0.3742	0.7287	−0.0089	0.115*
N2	0.07208 (9)	0.7091 (2)	0.41315 (16)	0.0544 (5)
O5	0.13958 (10)	1.0889 (2)	0.49361 (15)	0.0712 (5)
H5	0.1037	0.9853	0.4903	0.107*
O8	0.41724 (10)	0.9514 (2)	0.13122 (15)	0.0727 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0480 (10)	0.0591 (10)	0.0594 (11)	−0.0045 (7)	0.0065 (8)	−0.0027 (8)
C3	0.0467 (10)	0.0539 (9)	0.0494 (10)	0.0010 (7)	0.0029 (8)	−0.0004 (7)
C4	0.0494 (10)	0.0483 (9)	0.0486 (10)	0.0007 (7)	0.0001 (8)	0.0034 (6)
C5	0.0598 (12)	0.0495 (10)	0.0541 (10)	0.0057 (8)	0.0025 (9)	0.0020 (7)
C6	0.0718 (13)	0.0466 (9)	0.0672 (12)	−0.0003 (8)	−0.0038 (10)	−0.0033 (8)
C7	0.0652 (12)	0.0518 (10)	0.0696 (12)	−0.0104 (8)	−0.0025 (10)	0.0063 (9)
C8	0.0517 (11)	0.0589 (10)	0.0521 (10)	−0.0062 (7)	0.0040 (8)	0.0086 (7)
C9	0.0546 (11)	0.0514 (9)	0.0488 (10)	−0.0030 (7)	0.0044 (9)	−0.0013 (7)
C10	0.0628 (13)	0.0883 (14)	0.0793 (15)	−0.0105 (10)	0.0209 (11)	−0.0118 (11)
N2	0.0486 (9)	0.0571 (9)	0.0578 (9)	−0.0012 (6)	0.0068 (7)	−0.0004 (6)
O5	0.0726 (10)	0.0631 (8)	0.0789 (10)	0.0062 (6)	0.0182 (8)	−0.0140 (6)
O8	0.0643 (9)	0.0764 (9)	0.0786 (10)	−0.0194 (7)	0.0215 (7)	−0.0033 (7)

Geometric parameters (Å, º) top

C1—N2	1.455 (2)	C6—H6	0.93
C1—C1ⁱ	1.515 (3)	C7—C8	1.397 (2)
C1—H1A	0.97	C7—H7	0.93
C1—H1B	0.97	C8—O8	1.373 (2)
C3—N2	1.275 (2)	C8—C9	1.379 (2)
C3—C4	1.456 (2)	C9—H9	0.93
C3—H3	0.93	C10—O8	1.415 (2)
C4—C9	1.405 (2)	C10—H10A	0.96
C4—C5	1.408 (2)	C10—H10B	0.96
C5—O5	1.350 (2)	C10—H10C	0.96
C5—C6	1.391 (3)	O5—H5	0.82
C6—C7	1.366 (3)

N2—C1—C1ⁱ	109.99 (18)	C6—C7—C8	120.91 (16)
N2—C1—H1A	109.7	C6—C7—H7	119.5
C1ⁱ—C1—H1A	109.7	C8—C7—H7	119.5
N2—C1—H1B	109.7	O8—C8—C9	125.19 (16)
C1ⁱ—C1—H1B	109.7	O8—C8—C7	115.64 (15)
H1A—C1—H1B	108.2	C9—C8—C7	119.18 (17)
N2—C3—C4	121.80 (15)	C8—C9—C4	120.69 (16)
N2—C3—H3	119.1	C8—C9—H9	119.7
C4—C3—H3	119.1	C4—C9—H9	119.7
C9—C4—C5	119.26 (16)	O8—C10—H10A	109.5
C9—C4—C3	120.03 (15)	O8—C10—H10B	109.5
C5—C4—C3	120.68 (16)	H10A—C10—H10B	109.5
O5—C5—C6	119.26 (16)	O8—C10—H10C	109.5
O5—C5—C4	121.64 (16)	H10A—C10—H10C	109.5
C6—C5—C4	119.10 (17)	H10B—C10—H10C	109.5
C7—C6—C5	120.86 (16)	C3—N2—C1	119.31 (15)
C7—C6—H6	119.6	C5—O5—H5	109.5
C5—C6—H6	119.6	C8—O8—C10	117.41 (14)

N2—C3—C4—C9	179.47 (16)	C6—C7—C8—C9	1.2 (3)
N2—C3—C4—C5	1.4 (3)	O8—C8—C9—C4	178.87 (17)
C9—C4—C5—O5	−178.94 (15)	C7—C8—C9—C4	−0.8 (3)
C3—C4—C5—O5	−0.9 (3)	C5—C4—C9—C8	−0.2 (2)
C9—C4—C5—C6	0.8 (2)	C3—C4—C9—C8	−178.27 (15)
C3—C4—C5—C6	178.82 (15)	C4—C3—N2—C1	−178.95 (15)
O5—C5—C6—C7	179.38 (17)	C1ⁱ—C1—N2—C3	127.0 (2)
C4—C5—C6—C7	−0.3 (3)	C9—C8—O8—C10	−3.6 (3)
C5—C6—C7—C8	−0.7 (3)	C7—C8—O8—C10	176.06 (17)
C6—C7—C8—O8	−178.45 (17)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2	0.82	1.85	2.5844 (18)	148
C10—H10C···Cgⁱⁱ	0.96	2.64	3.521 (2)	152

Symmetry code: (ii) x, −y+1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O₄
M_r	328.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	15.0040 (12), 5.9722 (3), 9.3128 (8)
β (°)	92.001 (3)
V (Å³)	833.98 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.23 × 0.19

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3001, 1664, 1097
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.167, 1.05
No. of reflections	1664
No. of parameters	111
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.16

Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK (Otwinowski & Minor 1997), SIR2002 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2	0.8200	1.8500	2.5844 (18)	148
C10—H10C···Cgⁱ	0.96	2.64	3.521 (2)	152

Symmetry code: (i) x, −y+1/2, z−3/2.

Acknowledgements

The authors thank the Algerian Ministère de l'Enseignement Supérieur et de la Recherche Scientifique for financial support and Professor L. Ouahab (Laboratoire des Sciences Chimiques, Rennes1, France) for his valuable contribution and insightful discussions.

References

Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1760

doi:10.1107/S1600536812018405

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

2-[({2-[(2-Hy­dr­oxy-5-meth­­oxy­benzyl­­idene)amino]­eth­yl}imino)­meth­yl]-4-meth­­oxy­phenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[({2-[(2-Hydroxy-5-methoxybenzylidene)amino]ethyl}imino)methyl]-4-methoxyphenol