organic compounds
1-[4-({4-[(E)-(2-Hydroxynaphthalen-1-yl)methylideneamino]phenyl}sulfanyl)phenyl]ethanone
aDépartement de Chimie, Faculté des Sciences Exactes, Université Mentouri Constantine, Route de Ain El Bey, Constantine, Algeria, and bDépartement de Chimie Industrielle, Faculté des Sciences de l'Ingénieur, Université Mentouri Constantine, Campus Chaab Erssas, Constantine, Algeria
*Correspondence e-mail: abmousser@yahoo.fr
The title Schiff base compound, C25H19NO2S, crystallizes in a statistically disordered structure comprising keto and enol tautomeric forms. In the enol form, the benzenoid arrangment is promoted by a strong intramolecular O—H⋯N hydrogen bond and adopts an E conformation about the imine bond. In the keto form there is an intramolecular N—H⋯O hydrogen bond. In the crystal, an extended network of C—H⋯O hydrogen bonds stabilizes columns parallel to the c axis, forming large voids (there are four cavities of 108 Å3 per unit cell) with highly disordered residual electron density. The SQUEEZE procedure in PLATON [Spek (2009). Acta Cryst. D65, 148–155] was used to eliminate the contribution of this electron density from the intensity data, and the solvent-free model was employed for the final The contribution of this undetermined solvent was ignored in the calculation of the unit-cell characteristics.
Related literature
For related structures, see: Blagus & Kaitner (2011); Farag et al. (2010); Venkatachalam et al. (2011). For background to and their applications, see: Li et al. (2003); Villar et al. (2004); Kagkelari et al. (2009); Ourari et al. (2008); Zidane et al. (2011).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2006); cell SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
https://doi.org/10.1107/S1600536812049835/tk5178sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049835/tk5178Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812049835/tk5178Isup3.cml
The title Schiff base was prepared by the condensation of 4-amino-4-acetyl diphenylsulfide and 2-hydroxy naphthaldehyde in a 1:1 molar ratio in ethanol solution. The mixture was stirred under reflux three hours. The crystals of title compound crystallized from a mixture of chloroforme/hexane (1/1). The orange needles were collected by filtration and dried in air. Yield: 61%. Melting Point: 451 K.
H atoms were positioned geometrically, using a riding model with C—H = 0.98 Å [Uiso(H) = 1.5 × Ueq(methyl-C)] and with C—H = 0.95 Å [Uiso(H) =1.2 × Ueq(aromatic-C)]. The model included
about the C—C(methyl) bondSince one hydrogen is not very well localized between N13 and O1, the structure is described as the presence of two tautomers. Hydrogen is bonded to O1 in the first one (part A) and to N13 in the second (part B). This disorder was modeled by refining part A (except H on N13), with O—H = 0.84 Å (Uiso(H) = 1.5), and part B (except H on O1) with equivalence of N13 and central phenyl ring (C14 to C19) atoms, with N—H = 0.88 Å (Uiso(H) = 1.5).
Large voids in the structure contains residual electrons density with hight disorder and or thermal motions. The SQUEEZE procedure of PLATON was used to eliminate the contribution of this residual electron density from the intensity data, and the solvent-free model was employed for the final refinement.
Schiff bases are important compounds owing to their wide range of biological activities and industrial applications (Li et al., 2003; Villar et al., 2004). They have also been used as ligands in coordination chemistry (Kagkelari et al., 2009; Ourari et al. 2008; Zidane et al., 2011).
are generally synthesized by nucleophilic condensation of an aromatic amine and a carbonyl compound, followed by the dehydration of the hemiaminal intermediate to generate the imine (Blagus et al., 2011).In the present paper, we describe the synthesis and structural study of E-2-{[4-(4-acetylphenylsulfanyl)phenyl-amino]methyl} 2-oxo-naphthalene. The titled compound (Fig. 1) crystallizes in a disordered keto–amino tautomer [Csp2—O 1.277 (4) Å]. The C12—N13A bond length [1.334 (4) Å] is longer than C═N but in the same range of those observed in the literature for related compounds (Blagus et al., 2011; Farag et al., 2010; Venkatachalam et al., 2011) in accordance with the observed keto–amino tautomer form. The benzenoid arrangement is promoted by a strong intramolecular hydrogen bond O—H···N [N···O 2.558 (4) Å].
The Schiff base adopts a E conformation about the C12═N13 bond with a C11—C12—N13A—C14A torsion angle = -178.5 (3) Å. The central part of the molecule is planar with a dihedral angle between the benzene and naphthalene rings being less than 1 °. The molecule is twisted around the sulfide atom, so the average dihedral angle between the acetyl phenyl ring and the oxo naphthalen ring system is about 71°. The electron delocalisation between the two sulfur-bound lone pairs and π electrons of the adjacent phenyl rings leads to a slightly tighter Ssp3 angle (C17A—S1—C20 = 104.88 (15)°). The two similar sulfide carbone single bonds [C17A—S1 1.780 (3) Å and C20—S1 1.764 (3) Å] are as expected. The short bond C3—C4 distance [1.354 (5) Å] adjacent to the O1 oxygen atom of the naphthalen core indicates the presence of quinoid effect.
In the crystal, molecules are aligned head to foot along b axis, in columns parallel to [0 0 1] axis and the structure is stabilized by four kinds of C—H···O interactions (Fig. 2, Table 1). This arrangement separates the equivalent groups in columns by 4.444 (1) Å.
The large void channels in the structure (Fig. 3) contains residual electrons density with high disorder. The residual electron density were difficult to model and therefore, the SQUEEZE function of PLATON (Spek, 2009) was used to eliminate the contribution of the electron density in the solvent region from the intensity data, and the solvent-free model was employed for the final
There are four cavities of 108 Å3 per PLATON estimated that each cavity contains 12 electrons which may correspond to a solvent molecule.For related structures, see: Blagus et al. (2011); Farag et al. (2010); Venkatachalam et al. (2011). For background to
and their applications, see: Li et al. (2003); Villar et al. (2004); Kagkelari et al. (2009); Ourari et al. (2008); Zidane et al. (2011).Data collection: APEX2 (Bruker, 2006); cell
SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).C25H19NO2S | F(000) = 832 |
Mr = 397.47 | Dx = 1.265 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 1817 reflections |
a = 10.695 (3) Å | θ = 2.4–26.0° |
b = 44.458 (14) Å | µ = 0.18 mm−1 |
c = 4.4437 (11) Å | T = 150 K |
β = 99.004 (9)° | Stick, orange |
V = 2086.8 (10) Å3 | 0.58 × 0.17 × 0.06 mm |
Z = 4 |
Bruker APEXII diffractometer | 2952 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
CCD rotation images, thin slices scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS, Sheldrick, 2002) | h = −12→13 |
Tmin = 0.898, Tmax = 0.990 | k = −57→57 |
8026 measured reflections | l = −4→5 |
3680 independent reflections |
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)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0718P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.005 |
3680 reflections | Δρmax = 0.24 e Å−3 |
263 parameters | Δρmin = −0.22 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1291 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.06 (10) |
C25H19NO2S | V = 2086.8 (10) Å3 |
Mr = 397.47 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 10.695 (3) Å | µ = 0.18 mm−1 |
b = 44.458 (14) Å | T = 150 K |
c = 4.4437 (11) Å | 0.58 × 0.17 × 0.06 mm |
β = 99.004 (9)° |
Bruker APEXII diffractometer | 3680 independent reflections |
Absorption correction: multi-scan (SADABS, Sheldrick, 2002) | 2952 reflections with I > 2σ(I) |
Tmin = 0.898, Tmax = 0.990 | Rint = 0.036 |
8026 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.125 | Δρmax = 0.24 e Å−3 |
S = 0.98 | Δρmin = −0.22 e Å−3 |
3680 reflections | Absolute structure: Flack (1983), 1291 Friedel pairs |
263 parameters | Absolute structure parameter: −0.06 (10) |
2 restraints |
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. Since hydrogen is not very well localized between N13 and O1, the structure is described as the presence of two tautomers. Hydrogen is bonded to O1 in the first one (part A) and to N13 in the second (part B). This disorder was modeled by refining part A (except H on N13) and part B (except H on O1) with equivalence of N13 and central phenyl ring (C14 to C19) atoms. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1A | 0.9261 (2) | 0.89274 (5) | 0.2227 (5) | 0.0432 (6) | 0.5 |
H1A | 0.8804 | 0.8781 | 0.2548 | 0.065* | 0.5 |
O1B | 0.9261 (2) | 0.89274 (5) | 0.2227 (5) | 0.0432 (6) | 0.5 |
C2 | 0.8665 (3) | 0.90927 (7) | 0.0128 (7) | 0.0343 (7) | |
C3 | 0.9267 (3) | 0.93567 (7) | −0.0798 (8) | 0.0404 (8) | |
H3 | 1.0096 | 0.9405 | 0.0187 | 0.048* | |
C4 | 0.8695 (3) | 0.95396 (7) | −0.3033 (8) | 0.0404 (8) | |
H4 | 0.9135 | 0.9711 | −0.3594 | 0.048* | |
C5 | 0.7436 (3) | 0.94802 (7) | −0.4576 (7) | 0.0339 (7) | |
C6 | 0.6843 (4) | 0.96779 (7) | −0.6875 (8) | 0.0402 (8) | |
H6 | 0.7291 | 0.9849 | −0.7408 | 0.048* | |
C7 | 0.5643 (3) | 0.96264 (7) | −0.8334 (7) | 0.0423 (9) | |
H7 | 0.5253 | 0.9761 | −0.9862 | 0.051* | |
C8 | 0.4992 (4) | 0.93702 (8) | −0.7531 (7) | 0.0408 (8) | |
H8 | 0.4155 | 0.9332 | −0.853 | 0.049* | |
C9 | 0.5551 (3) | 0.91739 (7) | −0.5316 (8) | 0.0357 (7) | |
H9 | 0.5092 | 0.9003 | −0.4825 | 0.043* | |
C10 | 0.6785 (3) | 0.92219 (6) | −0.3773 (7) | 0.0317 (7) | |
C11 | 0.7411 (3) | 0.90245 (6) | −0.1401 (7) | 0.0306 (7) | |
C12 | 0.6792 (3) | 0.87685 (7) | −0.0513 (7) | 0.0321 (7) | |
H12 | 0.5963 | 0.8725 | −0.153 | 0.039* | |
N13A | 0.7319 (3) | 0.85845 (5) | 0.1698 (6) | 0.0320 (6) | 0.5 |
C14A | 0.6753 (3) | 0.83248 (6) | 0.2696 (7) | 0.0285 (6) | 0.5 |
C15A | 0.7471 (3) | 0.81538 (7) | 0.4960 (7) | 0.0325 (7) | 0.5 |
H15A | 0.8306 | 0.8216 | 0.5776 | 0.039* | 0.5 |
C16A | 0.6980 (3) | 0.78934 (7) | 0.6035 (7) | 0.0343 (7) | 0.5 |
H16A | 0.7467 | 0.7782 | 0.7626 | 0.041* | 0.5 |
C17A | 0.5781 (3) | 0.77958 (6) | 0.4798 (7) | 0.0296 (7) | 0.5 |
C18A | 0.5070 (3) | 0.79663 (7) | 0.2544 (7) | 0.0324 (7) | 0.5 |
H18A | 0.4242 | 0.7901 | 0.1706 | 0.039* | 0.5 |
C19A | 0.5541 (3) | 0.82303 (7) | 0.1483 (7) | 0.0345 (7) | 0.5 |
H19A | 0.504 | 0.8345 | −0.0058 | 0.041* | 0.5 |
N13B | 0.7319 (3) | 0.85845 (5) | 0.1698 (6) | 0.0320 (6) | 0.5 |
H13B | 0.8087 | 0.8629 | 0.2611 | 0.038* | 0.5 |
C14B | 0.6753 (3) | 0.83248 (6) | 0.2696 (7) | 0.0285 (6) | 0.5 |
C15B | 0.7471 (3) | 0.81538 (7) | 0.4960 (7) | 0.0325 (7) | 0.5 |
H15B | 0.8306 | 0.8216 | 0.5776 | 0.039* | 0.5 |
C16B | 0.6980 (3) | 0.78934 (7) | 0.6035 (7) | 0.0343 (7) | 0.5 |
H16B | 0.7467 | 0.7782 | 0.7626 | 0.041* | 0.5 |
C17B | 0.5781 (3) | 0.77958 (6) | 0.4798 (7) | 0.0296 (7) | 0.5 |
C18B | 0.5070 (3) | 0.79663 (7) | 0.2544 (7) | 0.0324 (7) | 0.5 |
H18B | 0.4242 | 0.7901 | 0.1706 | 0.039* | 0.5 |
C19B | 0.5541 (3) | 0.82303 (7) | 0.1483 (7) | 0.0345 (7) | 0.5 |
H19B | 0.504 | 0.8345 | −0.0058 | 0.041* | 0.5 |
S1 | 0.50675 (10) | 0.747532 (16) | 0.62296 (19) | 0.0362 (2) | |
C20 | 0.5814 (3) | 0.71639 (6) | 0.4809 (7) | 0.0288 (7) | |
C21 | 0.5376 (3) | 0.68797 (7) | 0.5525 (7) | 0.0342 (7) | |
H21 | 0.47 | 0.6864 | 0.6674 | 0.041* | |
C22 | 0.5921 (3) | 0.66202 (7) | 0.4567 (7) | 0.0344 (7) | |
H22 | 0.5608 | 0.6429 | 0.5051 | 0.041* | |
C23 | 0.6915 (3) | 0.66362 (7) | 0.2916 (7) | 0.0309 (7) | |
C24 | 0.7347 (3) | 0.69227 (7) | 0.2182 (7) | 0.0317 (7) | |
H24 | 0.8024 | 0.6938 | 0.1038 | 0.038* | |
C25 | 0.6800 (3) | 0.71807 (7) | 0.3103 (7) | 0.0305 (7) | |
H25 | 0.7098 | 0.7372 | 0.257 | 0.037* | |
C26 | 0.7554 (3) | 0.63638 (7) | 0.1932 (8) | 0.0367 (8) | |
C27 | 0.7015 (4) | 0.60589 (7) | 0.2401 (9) | 0.0474 (9) | |
H27A | 0.7546 | 0.5904 | 0.1671 | 0.071* | |
H27B | 0.6154 | 0.6046 | 0.1264 | 0.071* | |
H27C | 0.6992 | 0.6028 | 0.4576 | 0.071* | |
O28 | 0.8519 (3) | 0.63891 (6) | 0.0759 (6) | 0.0530 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0444 (14) | 0.0349 (12) | 0.0494 (16) | 0.0022 (10) | 0.0045 (11) | −0.0044 (10) |
O1B | 0.0444 (14) | 0.0349 (12) | 0.0494 (16) | 0.0022 (10) | 0.0045 (11) | −0.0044 (10) |
C2 | 0.044 (2) | 0.0286 (16) | 0.032 (2) | 0.0051 (14) | 0.0121 (14) | −0.0093 (13) |
C3 | 0.0406 (19) | 0.0355 (17) | 0.047 (2) | −0.0029 (15) | 0.0120 (16) | −0.0151 (15) |
C4 | 0.048 (2) | 0.0319 (16) | 0.046 (2) | −0.0078 (15) | 0.0241 (17) | −0.0102 (15) |
C5 | 0.048 (2) | 0.0278 (15) | 0.0299 (19) | −0.0021 (14) | 0.0177 (14) | −0.0072 (12) |
C6 | 0.064 (2) | 0.0293 (16) | 0.0320 (19) | −0.0051 (15) | 0.0218 (16) | −0.0041 (13) |
C7 | 0.061 (2) | 0.0339 (17) | 0.033 (2) | −0.0001 (16) | 0.0109 (17) | 0.0036 (14) |
C8 | 0.049 (2) | 0.0396 (18) | 0.034 (2) | 0.0013 (15) | 0.0062 (16) | −0.0023 (14) |
C9 | 0.048 (2) | 0.0294 (15) | 0.0310 (18) | −0.0037 (14) | 0.0092 (14) | −0.0008 (13) |
C10 | 0.0457 (19) | 0.0240 (13) | 0.0287 (18) | −0.0010 (13) | 0.0159 (14) | −0.0066 (12) |
C11 | 0.0410 (18) | 0.0249 (14) | 0.0279 (17) | −0.0011 (13) | 0.0112 (13) | −0.0068 (12) |
C12 | 0.0397 (18) | 0.0296 (15) | 0.0279 (18) | 0.0039 (13) | 0.0082 (13) | −0.0055 (12) |
N13A | 0.0375 (14) | 0.0286 (13) | 0.0308 (15) | 0.0022 (11) | 0.0082 (11) | −0.0019 (11) |
C14A | 0.0362 (17) | 0.0263 (14) | 0.0248 (17) | 0.0041 (12) | 0.0101 (12) | −0.0052 (12) |
C15A | 0.0359 (18) | 0.0332 (16) | 0.0278 (19) | 0.0001 (13) | 0.0034 (13) | −0.0021 (12) |
C16A | 0.0368 (18) | 0.0370 (17) | 0.0284 (19) | 0.0042 (14) | 0.0029 (14) | 0.0051 (13) |
C17A | 0.0358 (18) | 0.0267 (14) | 0.0270 (18) | 0.0034 (12) | 0.0069 (13) | 0.0017 (12) |
C18A | 0.0342 (17) | 0.0327 (16) | 0.0312 (19) | 0.0045 (13) | 0.0078 (13) | −0.0033 (12) |
C19A | 0.0403 (18) | 0.0311 (16) | 0.0311 (19) | 0.0048 (13) | 0.0030 (14) | 0.0036 (13) |
N13B | 0.0375 (14) | 0.0286 (13) | 0.0308 (15) | 0.0022 (11) | 0.0082 (11) | −0.0019 (11) |
C14B | 0.0362 (17) | 0.0263 (14) | 0.0248 (17) | 0.0041 (12) | 0.0101 (12) | −0.0052 (12) |
C15B | 0.0359 (18) | 0.0332 (16) | 0.0278 (19) | 0.0001 (13) | 0.0034 (13) | −0.0021 (12) |
C16B | 0.0368 (18) | 0.0370 (17) | 0.0284 (19) | 0.0042 (14) | 0.0029 (14) | 0.0051 (13) |
C17B | 0.0358 (18) | 0.0267 (14) | 0.0270 (18) | 0.0034 (12) | 0.0069 (13) | 0.0017 (12) |
C18B | 0.0342 (17) | 0.0327 (16) | 0.0312 (19) | 0.0045 (13) | 0.0078 (13) | −0.0033 (12) |
C19B | 0.0403 (18) | 0.0311 (16) | 0.0311 (19) | 0.0048 (13) | 0.0030 (14) | 0.0036 (13) |
S1 | 0.0411 (4) | 0.0342 (4) | 0.0357 (5) | 0.0028 (4) | 0.0138 (3) | 0.0048 (4) |
C20 | 0.0311 (16) | 0.0305 (15) | 0.0233 (18) | 0.0001 (12) | −0.0005 (12) | 0.0028 (12) |
C21 | 0.0350 (18) | 0.0354 (17) | 0.033 (2) | −0.0023 (13) | 0.0092 (13) | 0.0063 (13) |
C22 | 0.0394 (18) | 0.0310 (16) | 0.0326 (19) | −0.0070 (13) | 0.0047 (14) | 0.0037 (13) |
C23 | 0.0325 (17) | 0.0294 (15) | 0.0297 (18) | −0.0039 (12) | 0.0018 (13) | 0.0025 (12) |
C24 | 0.0325 (17) | 0.0331 (16) | 0.0296 (19) | −0.0035 (13) | 0.0049 (13) | 0.0028 (13) |
C25 | 0.0337 (17) | 0.0284 (15) | 0.0297 (18) | −0.0010 (12) | 0.0062 (13) | 0.0047 (12) |
C26 | 0.0362 (19) | 0.0362 (17) | 0.035 (2) | 0.0004 (14) | −0.0013 (14) | 0.0015 (14) |
C27 | 0.052 (2) | 0.0334 (17) | 0.057 (3) | 0.0055 (16) | 0.0088 (17) | 0.0002 (16) |
O28 | 0.0506 (16) | 0.0421 (14) | 0.0705 (18) | 0.0027 (12) | 0.0222 (13) | −0.0073 (13) |
O1A—C2 | 1.277 (4) | C15A—H15A | 0.95 |
O1A—H1A | 0.84 | C16A—C17A | 1.383 (5) |
C2—C3 | 1.429 (4) | C16A—H16A | 0.95 |
C2—C11 | 1.438 (5) | C17A—C18A | 1.385 (4) |
C3—C4 | 1.354 (5) | C17A—S1 | 1.780 (3) |
C3—H3 | 0.95 | C18A—C19A | 1.389 (4) |
C4—C5 | 1.437 (5) | C18A—H18A | 0.95 |
C4—H4 | 0.95 | C19A—H19A | 0.95 |
C5—C10 | 1.417 (4) | S1—C20 | 1.764 (3) |
C5—C6 | 1.420 (5) | C20—C25 | 1.394 (4) |
C6—C7 | 1.363 (5) | C20—C21 | 1.401 (4) |
C6—H6 | 0.95 | C21—C22 | 1.389 (4) |
C7—C8 | 1.410 (5) | C21—H21 | 0.95 |
C7—H7 | 0.95 | C22—C23 | 1.385 (5) |
C8—C9 | 1.380 (5) | C22—H22 | 0.95 |
C8—H8 | 0.95 | C23—C24 | 1.410 (4) |
C9—C10 | 1.404 (5) | C23—C26 | 1.489 (4) |
C9—H9 | 0.95 | C24—C25 | 1.378 (4) |
C10—C11 | 1.453 (4) | C24—H24 | 0.95 |
C11—C12 | 1.404 (4) | C25—H25 | 0.95 |
C12—N13A | 1.334 (4) | C26—O28 | 1.232 (4) |
C12—H12 | 0.95 | C26—C27 | 1.500 (4) |
N13A—C14A | 1.407 (4) | C27—H27A | 0.98 |
C14A—C19A | 1.388 (4) | C27—H27B | 0.98 |
C14A—C15A | 1.393 (5) | C27—H27C | 0.98 |
C15A—C16A | 1.387 (4) | ||
C2—O1A—H1A | 109.5 | C17A—C16A—C15A | 120.2 (3) |
O1A—C2—C3 | 119.1 (3) | C17A—C16A—H16A | 119.9 |
O1A—C2—C11 | 123.1 (3) | C15A—C16A—H16A | 119.9 |
C3—C2—C11 | 117.8 (3) | C16A—C17A—C18A | 119.1 (3) |
C4—C3—C2 | 122.1 (3) | C16A—C17A—S1 | 122.1 (2) |
C4—C3—H3 | 118.9 | C18A—C17A—S1 | 118.6 (2) |
C2—C3—H3 | 118.9 | C17A—C18A—C19A | 121.3 (3) |
C3—C4—C5 | 121.5 (3) | C17A—C18A—H18A | 119.3 |
C3—C4—H4 | 119.3 | C19A—C18A—H18A | 119.3 |
C5—C4—H4 | 119.3 | C18A—C19A—C14A | 119.4 (3) |
C10—C5—C6 | 120.1 (3) | C18A—C19A—H19A | 120.3 |
C10—C5—C4 | 119.3 (3) | C14A—C19A—H19A | 120.3 |
C6—C5—C4 | 120.6 (3) | C20—S1—C17A | 104.88 (15) |
C7—C6—C5 | 121.3 (3) | C25—C20—C21 | 118.7 (3) |
C7—C6—H6 | 119.4 | C25—C20—S1 | 125.2 (2) |
C5—C6—H6 | 119.4 | C21—C20—S1 | 116.1 (2) |
C6—C7—C8 | 118.7 (3) | C22—C21—C20 | 120.5 (3) |
C6—C7—H7 | 120.6 | C22—C21—H21 | 119.8 |
C8—C7—H7 | 120.6 | C20—C21—H21 | 119.8 |
C9—C8—C7 | 121.0 (3) | C23—C22—C21 | 120.9 (3) |
C9—C8—H8 | 119.5 | C23—C22—H22 | 119.5 |
C7—C8—H8 | 119.5 | C21—C22—H22 | 119.5 |
C8—C9—C10 | 121.4 (3) | C22—C23—C24 | 118.3 (3) |
C8—C9—H9 | 119.3 | C22—C23—C26 | 122.6 (3) |
C10—C9—H9 | 119.3 | C24—C23—C26 | 119.0 (3) |
C9—C10—C5 | 117.5 (3) | C25—C24—C23 | 120.9 (3) |
C9—C10—C11 | 123.6 (3) | C25—C24—H24 | 119.5 |
C5—C10—C11 | 118.9 (3) | C23—C24—H24 | 119.5 |
C12—C11—C2 | 119.0 (3) | C24—C25—C20 | 120.6 (3) |
C12—C11—C10 | 120.6 (3) | C24—C25—H25 | 119.7 |
C2—C11—C10 | 120.4 (3) | C20—C25—H25 | 119.7 |
N13A—C12—C11 | 122.7 (3) | O28—C26—C23 | 120.2 (3) |
N13A—C12—H12 | 118.7 | O28—C26—C27 | 120.4 (3) |
C11—C12—H12 | 118.7 | C23—C26—C27 | 119.3 (3) |
C12—N13A—C14A | 125.6 (3) | C26—C27—H27A | 109.5 |
C19A—C14A—C15A | 119.4 (3) | C26—C27—H27B | 109.5 |
C19A—C14A—N13A | 123.2 (3) | H27A—C27—H27B | 109.5 |
C15A—C14A—N13A | 117.4 (3) | C26—C27—H27C | 109.5 |
C16A—C15A—C14A | 120.6 (3) | H27A—C27—H27C | 109.5 |
C16A—C15A—H15A | 119.7 | H27B—C27—H27C | 109.5 |
C14A—C15A—H15A | 119.7 | ||
O1A—C2—C3—C4 | 179.2 (3) | C19A—C14A—C15A—C16A | −0.9 (5) |
C11—C2—C3—C4 | 0.0 (4) | N13A—C14A—C15A—C16A | −179.4 (3) |
C2—C3—C4—C5 | 0.9 (5) | C14A—C15A—C16A—C17A | 2.0 (5) |
C3—C4—C5—C10 | −0.9 (5) | C15A—C16A—C17A—C18A | −1.9 (5) |
C3—C4—C5—C6 | 178.8 (3) | C15A—C16A—C17A—S1 | −176.4 (2) |
C10—C5—C6—C7 | 0.6 (5) | C16A—C17A—C18A—C19A | 0.8 (5) |
C4—C5—C6—C7 | −179.2 (3) | S1—C17A—C18A—C19A | 175.5 (2) |
C5—C6—C7—C8 | −0.3 (5) | C17A—C18A—C19A—C14A | 0.3 (5) |
C6—C7—C8—C9 | −0.1 (5) | C15A—C14A—C19A—C18A | −0.2 (5) |
C7—C8—C9—C10 | 0.2 (5) | N13A—C14A—C19A—C18A | 178.1 (3) |
C8—C9—C10—C5 | 0.0 (5) | C16A—C17A—S1—C20 | −76.5 (3) |
C8—C9—C10—C11 | 179.2 (3) | C18A—C17A—S1—C20 | 109.0 (3) |
C6—C5—C10—C9 | −0.4 (4) | C17A—S1—C20—C25 | 3.5 (3) |
C4—C5—C10—C9 | 179.4 (3) | C17A—S1—C20—C21 | −177.5 (2) |
C6—C5—C10—C11 | −179.7 (3) | C25—C20—C21—C22 | 0.4 (4) |
C4—C5—C10—C11 | 0.1 (4) | S1—C20—C21—C22 | −178.6 (3) |
O1A—C2—C11—C12 | 1.6 (4) | C20—C21—C22—C23 | 0.7 (5) |
C3—C2—C11—C12 | −179.3 (3) | C21—C22—C23—C24 | −1.1 (4) |
O1A—C2—C11—C10 | −180.0 (3) | C21—C22—C23—C26 | 178.0 (3) |
C3—C2—C11—C10 | −0.8 (4) | C22—C23—C24—C25 | 0.5 (4) |
C9—C10—C11—C12 | 0.0 (5) | C26—C23—C24—C25 | −178.7 (3) |
C5—C10—C11—C12 | 179.2 (3) | C23—C24—C25—C20 | 0.6 (4) |
C9—C10—C11—C2 | −178.5 (3) | C21—C20—C25—C24 | −1.1 (4) |
C5—C10—C11—C2 | 0.8 (4) | S1—C20—C25—C24 | 177.9 (2) |
C2—C11—C12—N13A | −0.1 (4) | C22—C23—C26—O28 | −172.1 (3) |
C10—C11—C12—N13A | −178.5 (3) | C24—C23—C26—O28 | 7.0 (4) |
C11—C12—N13A—C14A | −180.0 (3) | C22—C23—C26—C27 | 7.5 (5) |
C12—N13A—C14A—C19A | −0.8 (5) | C24—C23—C26—C27 | −173.4 (3) |
C12—N13A—C14A—C15A | 177.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···N13A | 0.84 | 1.80 | 2.558 (4) | 149 |
N13B—H13B···O1B | 0.88 | 1.85 | 2.558 (4) | 136 |
C9—H9···O28i | 0.95 | 2.46 (1) | 3.398 (4) | 168 |
C19A—H19A···O28i | 0.95 | 2.56 (1) | 3.506 (4) | 174 |
C22—H22···O1Aii | 0.95 | 2.44 (1) | 3.337 (4) | 157 |
C27—H27B···O1Ai | 0.98 | 2.49 (1) | 3.442 (4) | 164 |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C25H19NO2S |
Mr | 397.47 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 150 |
a, b, c (Å) | 10.695 (3), 44.458 (14), 4.4437 (11) |
β (°) | 99.004 (9) |
V (Å3) | 2086.8 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.58 × 0.17 × 0.06 |
Data collection | |
Diffractometer | Bruker APEXII |
Absorption correction | Multi-scan (SADABS, Sheldrick, 2002) |
Tmin, Tmax | 0.898, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8026, 3680, 2952 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.125, 0.98 |
No. of reflections | 3680 |
No. of parameters | 263 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.22 |
Absolute structure | Flack (1983), 1291 Friedel pairs |
Absolute structure parameter | −0.06 (10) |
Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···N13A | 0.84 | 1.80 | 2.558 (4) | 149 |
N13B—H13B···O1B | 0.88 | 1.85 | 2.558 (4) | 136 |
C9—H9···O28i | 0.95 | 2.460 (0) | 3.398 (4) | 168 |
C19A—H19A···O28i | 0.95 | 2.559 (0) | 3.506 (4) | 174 |
C22—H22···O1Aii | 0.95 | 2.441 (0) | 3.337 (4) | 157 |
C27—H27B···O1Ai | 0.98 | 2.490 (1) | 3.442 (4) | 164 |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+3/2, z+1/2. |
Acknowledgements
The authors thank Dr Lahcène Ouahab and Thierry Roisnel from the Institut des Sciences Chimiques de Rennes UMR CNRS 6226 for the data collection and helpful discussions, and the Algerian Ministère de l'Enseignement Supérieur et de la Recherche Scientifique for financial support.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Schiff bases are important compounds owing to their wide range of biological activities and industrial applications (Li et al., 2003; Villar et al., 2004). They have also been used as ligands in coordination chemistry (Kagkelari et al., 2009; Ourari et al. 2008; Zidane et al., 2011). Schiff bases are generally synthesized by nucleophilic condensation of an aromatic amine and a carbonyl compound, followed by the dehydration of the hemiaminal intermediate to generate the imine (Blagus et al., 2011).
In the present paper, we describe the synthesis and structural study of E-2-{[4-(4-acetylphenylsulfanyl)phenyl-amino]methyl} 2-oxo-naphthalene. The titled compound (Fig. 1) crystallizes in a disordered keto–amino tautomer [Csp2—O 1.277 (4) Å]. The C12—N13A bond length [1.334 (4) Å] is longer than C═N but in the same range of those observed in the literature for related compounds (Blagus et al., 2011; Farag et al., 2010; Venkatachalam et al., 2011) in accordance with the observed keto–amino tautomer form. The benzenoid arrangement is promoted by a strong intramolecular hydrogen bond O—H···N [N···O 2.558 (4) Å].
The Schiff base adopts a E conformation about the C12═N13 bond with a C11—C12—N13A—C14A torsion angle = -178.5 (3) Å. The central part of the molecule is planar with a dihedral angle between the benzene and naphthalene rings being less than 1 °. The molecule is twisted around the sulfide atom, so the average dihedral angle between the acetyl phenyl ring and the oxo naphthalen ring system is about 71°. The electron delocalisation between the two sulfur-bound lone pairs and π electrons of the adjacent phenyl rings leads to a slightly tighter Ssp3 angle (C17A—S1—C20 = 104.88 (15)°). The two similar sulfide carbone single bonds [C17A—S1 1.780 (3) Å and C20—S1 1.764 (3) Å] are as expected. The short bond C3—C4 distance [1.354 (5) Å] adjacent to the O1 oxygen atom of the naphthalen core indicates the presence of quinoid effect.
In the crystal, molecules are aligned head to foot along b axis, in columns parallel to [0 0 1] axis and the structure is stabilized by four kinds of C—H···O interactions (Fig. 2, Table 1). This arrangement separates the equivalent groups in columns by 4.444 (1) Å.
The large void channels in the structure (Fig. 3) contains residual electrons density with high disorder. The residual electron density were difficult to model and therefore, the SQUEEZE function of PLATON (Spek, 2009) was used to eliminate the contribution of the electron density in the solvent region from the intensity data, and the solvent-free model was employed for the final refinement. There are four cavities of 108 Å3 per unit cell. PLATON estimated that each cavity contains 12 electrons which may correspond to a solvent molecule.