Crystal structure of (E)-1-[4-({4-[(4-meth­oxy­benzyl­idene)amino]­phen­yl}sulfan­yl)phen­yl]ethan-1-one

Rabihe Hebbachi; Amel Djedouani; Soumia Kadri; Hénia Mousser; Abdelhamid Mousser

doi:10.1107/S205698901500033X

. 2015 Jan 14;71(Pt 2):o109–o110. doi: 10.1107/S205698901500033X

Crystal structure of (E)-1-[4-({4-[(4-methoxybenzylidene)amino]phenyl}sulfanyl)phenyl]ethan-1-one

Rabihe Hebbachi ^a, Amel Djedouani ^b,^c, Soumia Kadri ^a, Hénia Mousser ^b,^c,^*, Abdelhamid Mousser ^a,^c

PMCID: PMC4384611 PMID: 25878856

Abstract

The title Schiff base compound, C₂₂H₁₉NO₂S, crystallized with two independent molecules (A and B) in the asymmetric unit. Both molecules have an E conformation about the C=N bond. The two molecules differ in the orientation of the aromatic rings with respect to each other. The outer 4-methoxybenzene ring is inclined to the central benzene ring and the outer 4-acetylbenzene ring by 1.80 (19) and 63.73 (19)°, respectively, in molecule A, and by 6.72 (18) and 68.53 (19)°, respectively, in molecule B. The two outer benzene rings are inclined to one another by 63.77 (18) and 63.19 (18)° in molecules A and B, respectively. In the crystal, the individual molecules stack in columns along [010], and are linked by a number of C—H⋯π interactions, forming slabs lying parallel to (001).

Keywords: crystal structure, Schiff base, 4-amino-4-acetyldiphenyl sulfide, C—H⋯π interactions

Related literature

For the synthesis and structures of Schiff bases, see, for example: Kahwa et al. (1986 ▸). For their use as protein and enzyme mimics, see: Santos et al. (2001 ▸). For their use as corrosion inhibitors, see: Ahamad et al. (2010 ▸); Negm et al. (2010 ▸). For their coordination properties, see: Özkar et al. (2004 ▸); Hebbachi & Benali-Cherif (2005 ▸). For complexation of Schiff bases with transition metals, see: Izatt et al. (1995 ▸); Kalcher et al. (1995 ▸). For the crystal structure of a very similar Schiff base compound derived from 4-amino-4-acetyldiphenyl sulfide, see: Hebbachi et al. (2013 ▸). graphic file with name e-71-0o109-scheme1.jpg

Experimental

Crystal data

C₂₂H₁₉NO₂S
M _r = 361.44
Triclinic,
a = 5.7708 (2) Å
b = 8.0867 (3) Å
c = 19.6929 (8) Å
α = 81.844 (2)°
β = 86.664 (3)°
γ = 85.662 (3)°
V = 906.05 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 K
0.1 × 0.1 × 0.1 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
19586 measured reflections
6013 independent reflections
4850 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.076
S = 1.03
6013 reflections
473 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack x determined using 1952 quotients [(I ⁺)−(I ⁻)]/[(I ⁺)+(I ⁻)] (Parsons et al., 2013 ▸)
Absolute structure parameter: 0.06 (3)

Data collection: SMART (Bruker, 2006 ▸); cell refinement: SAINT (Bruker, 2006 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and SHELXL2014.

Supplementary Material

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S205698901500033X/su5056sup1.cif

e-71-0o109-sup1.cif^{(596.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901500033X/su5056Isup2.hkl

e-71-0o109-Isup2.hkl^{(329.5KB, hkl)}

Click here for additional data file.^{(6.9KB, cml)}

Supporting information file. DOI: 10.1107/S205698901500033X/su5056Isup3.cml

Click here for additional data file.^{(1.6MB, tif)}

. DOI: 10.1107/S205698901500033X/su5056fig1.tif

The molecular structure of the two independent molecules (A and B) of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.^{(2.4MB, tif)}

b . DOI: 10.1107/S205698901500033X/su5056fig2.tif

A view along the b axis of the crystal packing of the title compound. C-H⋯π interactions are shown as dashed lines (see Table 1 for details; molecule A is red; molecule B is blue; H atoms not involved in these interactions have been omitted for clarity).

CCDC reference: 1042562

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

Cg1, Cg2, Cg3 and Cg6 are the centroids of the C2C7, C9C14, C15C20 and C37C42 rings, respectively.

DHA	DH	HA	D A	DHA
C17H17Cg6ⁱ	0.93	3.00	3.734(4)	137
C26H26Cg1	0.93	2.96	3.763(4)	146
C32H32Cg2	0.93	2.98	3.706(4)	136
C41H41Cg3ⁱⁱ	0.93	2.99	3.670(4)	131

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank the Algerian Ministère de l’Enseignement Supérieur et de la Recherche Scientifique for financial support.

supplementary crystallographic information

S1. Comment

The synthesis and structures of Schiff bases have attracted much attention in biology and chemistry (Kahwa et al., 1986). One of the aims of investigating their structural chemistry is to develop protein and enzyme mimics (Santos et al., 2001). Structural information is useful in investigating the coordination properties of Schiff bases functioning as ligands (Özkar et al., 2004; Hebbachi & Benali-Cherif, 2005). They have a great capacity for complexation of transition metals (Izatt et al., 1995; Kalcher et al., 1995). They are also used as corrosion inhibitors (Ahamad et al., 2010; Negm et al., 2010). There are only a few reported crystal structures of Schiff bases derived from 4-amino-4-acetyldiphenyl sulfide (Hebbachi et al., 2013). As a part of our ongoing research, we have synthesized the title compound and report herein on its crystal structure.

The title compound, Fig. 1, crystallized with two independent molecules (A and B) in the asymmetric unit. Both molecules have an E conformation about the C═N bond, with torsion angles C2—C1═N1—C9 and C24—C23═ N2—C31 being -179.9 (3) and 177.2 (3), respectively.

The two molecules differ in the orientation of the aromatic rings with respect to one another. The outer 4-methoxybenzene ring is inclined to the central benzene ring and the outer 3-acetylbenzene ring by 1.80 (19) and 63.73 (19) °, respectively, in molecule A, and by 6.72 (18) and 68.53 (19) °, respectively in molecule B. The two outer benzene rings are inclined to one another by 63.77 (18) and 63.19 (18) ° in molecules A and B, respectively.

The bond lengths and angles are close to those observed for a very similar structure, viz. (E)-1-(4-((4-(((4-hydroxynaphthalen-1-yl)methylene)amino)phenyl)thio) phenyl)ethan-1-one (Hebbachi et al., 2013). For example, the sulfur atom has sp³ hybridization as indicated by the C—S—C angle of 106.01 (15) and 105.99 (15) ° in molecules A and B, respectively, compared to 104.88 (15) ° observed in the above mentioned compound.

In the crystal, molecules stack along [010] in columns composed of either A or B molecules, and are linked by a number of C-H···π interactions (Table 1 and Fig. 2) forming slabs lying parallel to (001).

S2. Experimental

The title Schiff base was prepared by condensation of 4-amino-4-acetyl diphenylsulfure and anisaldehyde in a 1:1 molar ratio, in an ethanol solution containing a few drops of dry piperidine. The mixture was stirred under reflux for 3 h. The mixture was then concentrated and cooled. Colourless prismatic crystals of title compound were obtained by recrystallization from a mixture of chloroform/hexane (1/1). They were collected by filtration and dried in air (yield: 64%; m.p.: 421 K).