organic compounds
1-[(E)-2-(5-tert-Butyl-2-hydroxyphenyl)diazen-1-yl]naphthalen-2-ol
aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Département de Chimie, Université Mentouri de Constantine 1, 25000 Constantine, Algeria
*Correspondence e-mail: bougueriahassiba@gmail.com
The non-H atoms of the title compound, C20H20N2O2, is located on a mirror plane except two methyl groups of the tert-butyl group. Intramolecular N—H⋯O hydrogen bonds exist between the hydroxy and diazenyl groups. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds into supramolecular chains running along the a-axis direction.
CCDC reference: 983246
Related literature
For general background to et al. (2004). For related see: Yazıcı et al. (2010); Karadayı et al. (2006); Oakes (2002); Olivieri et al. (1989). For the synthesis, see: Wang et al. (2003).
and their use in dyes, pigments and advanced materials, see: LeeExperimental
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
CCDC reference: 983246
10.1107/S1600536814001731/xu5764sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001731/xu5764Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001731/xu5764Isup3.cml
The title compound was obtained through the diazotization of 4-tert-butyl-2-hydroxyaniline followed by a coupling reaction with 2-naphthol, according to the literature procedure used to synthesize other aromatic azo-compounds (Wang et al., 2003). Single crystals of the title compound were obtained by slow evaporation at room temperature of a solution in DMSO.
H atoms, attached to carbon atoms have been placed in geometrically idealized positions and refined as riding, with C—H = 0.93 (aromatic) and 0.96 Å (methyl), and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). hydroxy H atoms were introduced in calculated positions and treated as riding on their parent atoms with O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O).
Azo compounds are very important in the fields of dyes, pigments and advanced materials (Lee et al., 2004). Azo dyes are synthetic colours that contain an azo group, as part of the structure. We are involved in the color generation mechanism of azo pigments typically characterized by the chromophore of the azo group (–N=N–). However, some types of azo pigments are also known to possess the hydrazone structure (=N–NH–), often leading to the formation of intramolecular hydrogen bonds. The azo– hydrazone
in azo dyes has been known for more than a hundred years and is directly connected with the presence of at least one protic donor group in conjugation to the azo bridge (i.e. 2-naphthol) (Olivieri et al.., 1989). In particular, azo dyes that contain a naphtholic hydroxy group conjugated with the azo linkage exist in aqueous solution as an equilibrium mixture of two chemically distinct tautomers, the azo or hydrazone forms (Oakes, 2002). It is suggested that in a real azo compound the N=N double bond should have a length of 1.20–1.28 Å and the bond length of N–N single bonds, as in hydrazone tautomers, should be more than 1.4 Å. In the title compound, N–N bond lengths are 1.287 Å for N1–N2 , between the suggested N=N double bond and N–N single bond lengths. In the molecule, all bond lengths are in good agreement with those reported for other (Yazıcı et al., 2010; Karadayı et al., 2006). We report here in the of the title compound, obtained through the diazotization of 4-tert-butyl-2-hydroxy aniline followed by a coupling reaction with 2-naphthol.The molecule of the title compound, with the atom numbering scheme, is shown in Fig. 1, crystallizes in the monoclinic
P21/m. The molecular structure C20H20N2O2 is shown in Figure 1 The molecule adopts an anti–configuration with the two reside on the opposite side of azo–group. The intramolecular N—H···O hydrogen bond is found (Table 1). In the crystal molecules are linked by the weak C—H···O interactions into chains.For general background to
and their use in dyes, pigments and advanced materials, see: Lee et al. (2004). For related see: Yazıcı et al. (2010); Karadayı et al. (2006); Oakes (2002); Olivieri et al. (1989). For the synthesis, see: Wang et al. (2003).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).Fig. 1. The molecular structure of the title compound, displacement ellipsoids are drawn at 50% probability level. |
C20H20N2O2 | F(000) = 340 |
Mr = 320.38 | Dx = 1.323 Mg m−3 |
Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yb | Cell parameters from 2015 reflections |
a = 9.696 (5) Å | θ = 3.2–30.4° |
b = 6.606 (5) Å | µ = 0.09 mm−1 |
c = 13.385 (5) Å | T = 293 K |
β = 110.249 (5)° | Prism, red |
V = 804.3 (8) Å3 | 0.55 × 0.22 × 0.11 mm |
Z = 2 |
Bruker APEXII diffractometer | 2642 independent reflections |
Radiation source: fine-focus sealed tube | 1767 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
CCD rotation images, thin slices scans | θmax = 30.5°, θmin = 3.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −13→13 |
Tmin = 0.978, Tmax = 0.991 | k = −7→9 |
8889 measured reflections | l = −18→19 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 0.89 | w = 1/[σ2(Fo2) + (0.0766P)2 + 0.359P] where P = (Fo2 + 2Fc2)/3 |
2642 reflections | (Δ/σ)max < 0.001 |
142 parameters | Δρmax = 0.43 e Å−3 |
12 restraints | Δρmin = −0.23 e Å−3 |
C20H20N2O2 | V = 804.3 (8) Å3 |
Mr = 320.38 | Z = 2 |
Monoclinic, P21/m | Mo Kα radiation |
a = 9.696 (5) Å | µ = 0.09 mm−1 |
b = 6.606 (5) Å | T = 293 K |
c = 13.385 (5) Å | 0.55 × 0.22 × 0.11 mm |
β = 110.249 (5)° |
Bruker APEXII diffractometer | 2642 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 1767 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.991 | Rint = 0.025 |
8889 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 12 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 0.89 | Δρmax = 0.43 e Å−3 |
2642 reflections | Δρmin = −0.23 e Å−3 |
142 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.77215 (13) | 0.75000 | 0.56321 (10) | 0.0270 (4) | |
O2 | 0.31274 (13) | 0.75000 | 0.19510 (10) | 0.0277 (4) | |
N1 | 0.48377 (15) | 0.75000 | 0.39638 (11) | 0.0180 (4) | |
N2 | 0.60014 (15) | 0.75000 | 0.37081 (11) | 0.0194 (4) | |
C1 | 0.50711 (18) | 0.75000 | 0.50553 (13) | 0.0164 (4) | |
C2 | 0.64717 (17) | 0.75000 | 0.58490 (14) | 0.0195 (4) | |
C3 | 0.66094 (19) | 0.75000 | 0.69373 (14) | 0.0242 (5) | |
C4 | 0.53890 (19) | 0.75000 | 0.72205 (14) | 0.0240 (5) | |
C5 | 0.39521 (18) | 0.75000 | 0.64529 (14) | 0.0191 (5) | |
C6 | 0.37768 (17) | 0.75000 | 0.53520 (13) | 0.0172 (4) | |
C7 | 0.23305 (19) | 0.75000 | 0.46054 (15) | 0.0258 (5) | |
C8 | 0.1138 (2) | 0.75000 | 0.49354 (16) | 0.0326 (6) | |
C9 | 0.1312 (2) | 0.75000 | 0.60179 (16) | 0.0300 (6) | |
C10 | 0.2695 (2) | 0.75000 | 0.67614 (15) | 0.0246 (5) | |
C11 | 0.57989 (18) | 0.75000 | 0.26191 (13) | 0.0190 (4) | |
C12 | 0.44281 (18) | 0.75000 | 0.17815 (14) | 0.0209 (5) | |
C13 | 0.44203 (19) | 0.75000 | 0.07401 (14) | 0.0259 (5) | |
C14 | 0.5727 (2) | 0.75000 | 0.05311 (14) | 0.0254 (5) | |
C15 | 0.71035 (18) | 0.75000 | 0.13444 (13) | 0.0195 (5) | |
C16 | 0.70929 (18) | 0.75000 | 0.23809 (14) | 0.0203 (5) | |
C17 | 0.85759 (19) | 0.75000 | 0.11508 (14) | 0.0220 (5) | |
C18 | 0.94634 (15) | 0.5609 (2) | 0.16604 (12) | 0.0300 (4) | |
C19 | 0.8368 (2) | 0.75000 | −0.00394 (16) | 0.0327 (6) | |
H1 | 0.75270 | 0.75000 | 0.49850 | 0.0410* | |
H2 | 0.32790 | 0.75000 | 0.25930 | 0.0420* | |
H3 | 0.75380 | 0.75000 | 0.74610 | 0.0290* | |
H4 | 0.55030 | 0.75000 | 0.79390 | 0.0290* | |
H7 | 0.21840 | 0.75000 | 0.38810 | 0.0310* | |
H8 | 0.01970 | 0.75000 | 0.44290 | 0.0390* | |
H9 | 0.04930 | 0.75000 | 0.62290 | 0.0360* | |
H10 | 0.28130 | 0.75000 | 0.74810 | 0.0300* | |
H13 | 0.35290 | 0.75000 | 0.01770 | 0.0310* | |
H14 | 0.56850 | 0.75000 | −0.01730 | 0.0310* | |
H16 | 0.79880 | 0.75000 | 0.29410 | 0.0240* | |
H18A | 0.89250 | 0.44160 | 0.13420 | 0.0360* | |
H18B | 0.96370 | 0.56020 | 0.24120 | 0.0360* | |
H18C | 1.03870 | 0.56280 | 0.15450 | 0.0360* | |
H19A | 0.78450 | 0.63120 | −0.03610 | 0.0390* | |
H19B | 0.93110 | 0.75000 | −0.01250 | 0.0390* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0180 (6) | 0.0410 (8) | 0.0236 (6) | 0.0000 | 0.0091 (5) | 0.0000 |
O2 | 0.0191 (6) | 0.0418 (8) | 0.0233 (6) | 0.0000 | 0.0088 (5) | 0.0000 |
N1 | 0.0201 (6) | 0.0172 (7) | 0.0188 (7) | 0.0000 | 0.0096 (5) | 0.0000 |
N2 | 0.0208 (6) | 0.0220 (7) | 0.0178 (7) | 0.0000 | 0.0096 (5) | 0.0000 |
C1 | 0.0192 (7) | 0.0150 (7) | 0.0162 (7) | 0.0000 | 0.0078 (6) | 0.0000 |
C2 | 0.0174 (7) | 0.0202 (8) | 0.0219 (8) | 0.0000 | 0.0082 (6) | 0.0000 |
C3 | 0.0207 (8) | 0.0303 (10) | 0.0193 (8) | 0.0000 | 0.0040 (6) | 0.0000 |
C4 | 0.0272 (8) | 0.0282 (10) | 0.0169 (8) | 0.0000 | 0.0080 (7) | 0.0000 |
C5 | 0.0224 (8) | 0.0173 (8) | 0.0198 (8) | 0.0000 | 0.0100 (6) | 0.0000 |
C6 | 0.0201 (7) | 0.0146 (8) | 0.0185 (8) | 0.0000 | 0.0086 (6) | 0.0000 |
C7 | 0.0208 (8) | 0.0371 (11) | 0.0194 (8) | 0.0000 | 0.0070 (7) | 0.0000 |
C8 | 0.0188 (8) | 0.0494 (13) | 0.0298 (10) | 0.0000 | 0.0085 (7) | 0.0000 |
C9 | 0.0238 (8) | 0.0384 (11) | 0.0331 (10) | 0.0000 | 0.0165 (8) | 0.0000 |
C10 | 0.0298 (9) | 0.0260 (9) | 0.0232 (9) | 0.0000 | 0.0159 (7) | 0.0000 |
C11 | 0.0212 (7) | 0.0197 (8) | 0.0177 (8) | 0.0000 | 0.0087 (6) | 0.0000 |
C12 | 0.0191 (7) | 0.0217 (9) | 0.0233 (8) | 0.0000 | 0.0093 (6) | 0.0000 |
C13 | 0.0213 (8) | 0.0357 (11) | 0.0187 (8) | 0.0000 | 0.0044 (6) | 0.0000 |
C14 | 0.0296 (9) | 0.0324 (10) | 0.0160 (8) | 0.0000 | 0.0102 (7) | 0.0000 |
C15 | 0.0232 (8) | 0.0183 (8) | 0.0204 (8) | 0.0000 | 0.0117 (7) | 0.0000 |
C16 | 0.0196 (7) | 0.0238 (9) | 0.0193 (8) | 0.0000 | 0.0089 (6) | 0.0000 |
C17 | 0.0248 (8) | 0.0242 (9) | 0.0218 (8) | 0.0000 | 0.0142 (7) | 0.0000 |
C18 | 0.0306 (6) | 0.0293 (7) | 0.0356 (7) | 0.0053 (6) | 0.0185 (5) | 0.0029 (6) |
C19 | 0.0347 (10) | 0.0448 (13) | 0.0256 (9) | 0.0000 | 0.0194 (8) | 0.0000 |
O1—C2 | 1.340 (2) | C14—C15 | 1.400 (3) |
O2—C12 | 1.357 (3) | C15—C17 | 1.537 (3) |
O1—H1 | 0.8200 | C15—C16 | 1.391 (3) |
O2—H2 | 0.8200 | C17—C18i | 1.536 (2) |
N1—C1 | 1.399 (2) | C17—C18 | 1.536 (2) |
N1—N2 | 1.288 (2) | C17—C19 | 1.535 (3) |
N2—C11 | 1.402 (2) | C3—H3 | 0.9300 |
C1—C6 | 1.441 (3) | C4—H4 | 0.9300 |
C1—C2 | 1.405 (3) | C7—H7 | 0.9300 |
C2—C3 | 1.416 (3) | C8—H8 | 0.9300 |
C3—C4 | 1.362 (3) | C9—H9 | 0.9300 |
C4—C5 | 1.416 (3) | C10—H10 | 0.9300 |
C5—C6 | 1.424 (3) | C13—H13 | 0.9300 |
C5—C10 | 1.416 (3) | C14—H14 | 0.9300 |
C6—C7 | 1.413 (3) | C16—H16 | 0.9300 |
C7—C8 | 1.373 (3) | C18—H18A | 0.9600 |
C8—C9 | 1.400 (3) | C18—H18B | 0.9600 |
C9—C10 | 1.366 (3) | C18—H18C | 0.9600 |
C11—C12 | 1.411 (3) | C19—H19A | 0.9500 |
C11—C16 | 1.397 (3) | C19—H19B | 0.9600 |
C12—C13 | 1.391 (3) | C19—H19Ai | 0.9500 |
C13—C14 | 1.389 (3) | ||
O1···N1 | 2.913 (3) | C11···C4iii | 3.529 (3) |
O1···N2 | 2.538 (3) | C11···C4iv | 3.529 (3) |
O1···C9ii | 3.338 (4) | C11···C4v | 3.529 (3) |
O1···C7iii | 3.317 (3) | C11···C5iv | 3.508 (3) |
O1···C7iv | 3.317 (3) | C11···C5v | 3.508 (3) |
O1···C7v | 3.317 (3) | C11···C10iv | 3.591 (3) |
O1···C7vi | 3.317 (3) | C11···C10v | 3.591 (3) |
O1···C9vii | 3.338 (4) | C11···C5vi | 3.508 (3) |
O2···N1 | 2.630 (3) | C11···C4vi | 3.529 (3) |
O2···N2 | 2.960 (3) | C11···C5iii | 3.508 (3) |
O1···H9vii | 2.5200 | C11···C10iii | 3.591 (3) |
O1···H9ii | 2.5200 | C11···C10vi | 3.591 (3) |
O2···H18Cviii | 2.8100 | C12···C4iii | 3.544 (3) |
O2···H18Cix | 2.8100 | C12···C4iv | 3.544 (3) |
N1···O1 | 2.913 (3) | C12···C4v | 3.544 (3) |
N1···O2 | 2.630 (3) | C12···C4vi | 3.544 (3) |
N2···C5iv | 3.311 (3) | C16···C10iii | 3.480 (3) |
N2···C5v | 3.311 (3) | C16···C10iv | 3.480 (3) |
N2···C5iii | 3.311 (3) | C16···C10v | 3.480 (3) |
N2···O1 | 2.538 (3) | C16···C10vi | 3.480 (3) |
N2···O2 | 2.960 (3) | C11···H1 | 3.0300 |
N2···C5vi | 3.311 (3) | C14···H19Ai | 2.8200 |
N1···H2 | 1.9300 | C14···H19A | 2.8200 |
N1···H7 | 2.5400 | C16···H18B | 2.7500 |
N1···H1 | 2.4900 | C16···H18Bi | 2.7500 |
N2···H1 | 1.8300 | C18···H16 | 2.8700 |
N2···H2 | 2.5400 | C19···H14 | 2.5500 |
C1···C1iv | 3.307 (3) | H1···N1 | 2.4900 |
C1···C1v | 3.307 (3) | H1···N2 | 1.8300 |
C1···C6iv | 3.588 (3) | H1···C11 | 3.0300 |
C1···C6v | 3.588 (3) | H2···N1 | 1.9300 |
C1···C1iii | 3.307 (3) | H2···N2 | 2.5400 |
C1···C1vi | 3.307 (3) | H2···H7 | 2.3200 |
C1···C6iii | 3.588 (3) | H4···H10 | 2.4600 |
C1···C6vi | 3.588 (3) | H4···H14x | 2.4700 |
C4···C11iv | 3.529 (3) | H4···H14xi | 2.4700 |
C4···C11v | 3.529 (3) | H7···N1 | 2.5400 |
C4···C12iv | 3.544 (3) | H7···H2 | 2.3200 |
C4···C12v | 3.544 (3) | H8···H16viii | 2.3700 |
C4···C11iii | 3.529 (3) | H8···H16ix | 2.3700 |
C4···C11vi | 3.529 (3) | H9···O1viii | 2.5200 |
C4···C12iii | 3.544 (3) | H9···O1ix | 2.5200 |
C4···C12vi | 3.544 (3) | H10···H4 | 2.4600 |
C5···N2iv | 3.311 (3) | H14···C19 | 2.5500 |
C5···N2v | 3.311 (3) | H14···H4xii | 2.4700 |
C5···C11iv | 3.508 (3) | H14···H19A | 2.3300 |
C5···C11v | 3.508 (3) | H14···H4xiii | 2.4700 |
C5···N2iii | 3.311 (3) | H14···H19Ai | 2.3300 |
C5···N2vi | 3.311 (3) | H16···C18 | 2.8700 |
C5···C11iii | 3.508 (3) | H16···H8ii | 2.3700 |
C5···C11vi | 3.508 (3) | H16···H18B | 2.3300 |
C6···C1iv | 3.588 (3) | H16···C18i | 2.8700 |
C6···C1v | 3.588 (3) | H16···H8vii | 2.3700 |
C6···C1iii | 3.588 (3) | H16···H18Bi | 2.3300 |
C6···C1vi | 3.588 (3) | H18A···H19A | 2.4900 |
C7···O1iv | 3.317 (3) | H18A···H18Axiv | 2.5300 |
C7···O1v | 3.317 (3) | H18B···C16 | 2.7500 |
C7···O1iii | 3.317 (3) | H18B···H16 | 2.3300 |
C7···O1vi | 3.317 (3) | H18B···H18Bi | 2.5100 |
C9···O1viii | 3.338 (4) | H18C···O2ii | 2.8100 |
C9···O1ix | 3.338 (4) | H18C···H19B | 2.4500 |
C10···C11iv | 3.591 (3) | H18C···O2vii | 2.8100 |
C10···C11v | 3.591 (3) | H18C···H18Ci | 2.4700 |
C10···C16iv | 3.480 (3) | H19A···C14 | 2.8200 |
C10···C16v | 3.480 (3) | H19A···H14 | 2.3300 |
C10···C11iii | 3.591 (3) | H19A···H18A | 2.4900 |
C10···C11vi | 3.591 (3) | H19B···H18C | 2.4500 |
C10···C16iii | 3.480 (3) | H19B···H18Ci | 2.4500 |
C10···C16vi | 3.480 (3) | ||
C2—O1—H1 | 110.00 | C15—C17—C18i | 109.60 (10) |
C12—O2—H2 | 110.00 | C18—C17—C18i | 108.81 (14) |
N2—N1—C1 | 115.96 (14) | C18i—C17—C19 | 108.24 (11) |
N1—N2—C11 | 117.14 (14) | C18—C17—C19 | 108.24 (11) |
N1—C1—C6 | 116.50 (15) | C15—C17—C18 | 109.60 (10) |
N1—C1—C2 | 123.67 (16) | C2—C3—H3 | 120.00 |
C2—C1—C6 | 119.84 (15) | C4—C3—H3 | 120.00 |
O1—C2—C3 | 116.90 (16) | C3—C4—H4 | 119.00 |
O1—C2—C1 | 123.09 (16) | C5—C4—H4 | 119.00 |
C1—C2—C3 | 120.01 (16) | C6—C7—H7 | 120.00 |
C2—C3—C4 | 120.31 (17) | C8—C7—H7 | 120.00 |
C3—C4—C5 | 121.97 (16) | C7—C8—H8 | 119.00 |
C4—C5—C10 | 121.23 (16) | C9—C8—H8 | 119.00 |
C6—C5—C10 | 119.70 (16) | C8—C9—H9 | 120.00 |
C4—C5—C6 | 119.07 (16) | C10—C9—H9 | 120.00 |
C5—C6—C7 | 117.77 (16) | C5—C10—H10 | 119.00 |
C1—C6—C5 | 118.80 (15) | C9—C10—H10 | 120.00 |
C1—C6—C7 | 123.43 (15) | C12—C13—H13 | 120.00 |
C6—C7—C8 | 120.85 (17) | C14—C13—H13 | 120.00 |
C7—C8—C9 | 121.32 (19) | C13—C14—H14 | 119.00 |
C8—C9—C10 | 119.38 (19) | C15—C14—H14 | 119.00 |
C5—C10—C9 | 120.99 (18) | C11—C16—H16 | 119.00 |
C12—C11—C16 | 119.46 (16) | C15—C16—H16 | 118.00 |
N2—C11—C12 | 125.48 (16) | C17—C18—H18A | 110.00 |
N2—C11—C16 | 115.06 (15) | C17—C18—H18B | 110.00 |
C11—C12—C13 | 118.22 (17) | C17—C18—H18C | 109.00 |
O2—C12—C13 | 118.99 (16) | H18A—C18—H18B | 109.00 |
O2—C12—C11 | 122.79 (16) | H18A—C18—H18C | 109.00 |
C12—C13—C14 | 120.85 (17) | H18B—C18—H18C | 109.00 |
C13—C14—C15 | 122.27 (16) | C17—C19—H19A | 109.00 |
C16—C15—C17 | 119.75 (15) | C17—C19—H19B | 110.00 |
C14—C15—C16 | 116.19 (17) | C17—C19—H19Ai | 109.00 |
C14—C15—C17 | 124.06 (15) | H19A—C19—H19B | 109.00 |
C11—C16—C15 | 123.01 (16) | H19A—C19—H19Ai | 111.00 |
C15—C17—C19 | 112.28 (15) | H19Ai—C19—H19B | 109.00 |
C1—N1—N2—C11 | 180.00 (1) | C6—C5—C10—C9 | 0.00 (1) |
N2—N1—C1—C2 | 0.00 (1) | C1—C6—C7—C8 | 180.00 (1) |
N2—N1—C1—C6 | 180.00 (1) | C5—C6—C7—C8 | 0.00 (1) |
N1—N2—C11—C12 | 0.00 (1) | C6—C7—C8—C9 | 0.00 (1) |
N1—N2—C11—C16 | 180.00 (1) | C7—C8—C9—C10 | 0.00 (1) |
N1—C1—C2—O1 | 0.00 (1) | C8—C9—C10—C5 | 0.00 (1) |
N1—C1—C2—C3 | 180.00 (1) | N2—C11—C12—O2 | 0.00 (1) |
C6—C1—C2—O1 | 180.00 (1) | N2—C11—C12—C13 | 180.00 (1) |
C6—C1—C2—C3 | 0.00 (1) | C16—C11—C12—O2 | 180.00 (1) |
N1—C1—C6—C5 | 180.00 (1) | C16—C11—C12—C13 | 0.00 (1) |
N1—C1—C6—C7 | 0.00 (1) | N2—C11—C16—C15 | 180.00 (1) |
C2—C1—C6—C5 | 0.00 (1) | C12—C11—C16—C15 | 0.00 (1) |
C2—C1—C6—C7 | 180.00 (1) | O2—C12—C13—C14 | 180.00 (1) |
O1—C2—C3—C4 | 180.00 (1) | C11—C12—C13—C14 | 0.00 (1) |
C1—C2—C3—C4 | 0.00 (1) | C12—C13—C14—C15 | 0.00 (1) |
C2—C3—C4—C5 | 0.00 (1) | C13—C14—C15—C16 | 0.00 (1) |
C3—C4—C5—C6 | 0.00 (1) | C13—C14—C15—C17 | 180.00 (1) |
C3—C4—C5—C10 | 180.00 (1) | C14—C15—C16—C11 | 0.00 (1) |
C4—C5—C6—C1 | 0.00 (1) | C17—C15—C16—C11 | 180.00 (1) |
C4—C5—C6—C7 | 180.00 (1) | C14—C15—C17—C18 | −120.32 (10) |
C10—C5—C6—C1 | 180.00 (1) | C14—C15—C17—C19 | 0.00 (1) |
C10—C5—C6—C7 | 0.00 (1) | C16—C15—C17—C18 | 59.68 (10) |
C4—C5—C10—C9 | 180.00 (1) | C16—C15—C17—C19 | 180.00 (1) |
Symmetry codes: (i) x, −y+3/2, z; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, y−1/2, −z+1; (v) −x+1, y+1/2, −z+1; (vi) −x+1, −y+2, −z+1; (vii) x+1, −y+3/2, z; (viii) x−1, y, z; (ix) x−1, −y+3/2, z; (x) x, y, z+1; (xi) x, −y+3/2, z+1; (xii) x, y, z−1; (xiii) x, −y+3/2, z−1; (xiv) x, −y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.82 | 1.83 | 2.538 (3) | 143 |
O2—H2···N1 | 0.82 | 1.93 | 2.630 (3) | 142 |
C9—H9···O1viii | 0.93 | 2.52 | 3.338 (4) | 146 |
Symmetry code: (viii) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.82 | 1.83 | 2.538 (3) | 143 |
O2—H2···N1 | 0.82 | 1.93 | 2.630 (3) | 142 |
C9—H9···O1i | 0.93 | 2.52 | 3.338 (4) | 146 |
Symmetry code: (i) x−1, y, z. |
Acknowledgements
We thank all researchers of the CHEMS Research Unit of the University of Constantine, Algeria, for the valuable assistance they have provided us throughout the realisation of this work. We also express our gratitude and thank Mr L. Ouahab, Director of Research at the laboratory UMR LCSIM 6511, CNRS, Rennes I (France), for his valuable collaboration in the recording and interpretation of the XRD data.
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Azo compounds are very important in the fields of dyes, pigments and advanced materials (Lee et al., 2004). Azo dyes are synthetic colours that contain an azo group, as part of the structure. We are involved in the color generation mechanism of azo pigments typically characterized by the chromophore of the azo group (–N=N–). However, some types of azo pigments are also known to possess the hydrazone structure (=N–NH–), often leading to the formation of intramolecular hydrogen bonds. The azo– hydrazone tautomerism in azo dyes has been known for more than a hundred years and is directly connected with the presence of at least one protic donor group in conjugation to the azo bridge (i.e. 2-naphthol) (Olivieri et al.., 1989). In particular, azo dyes that contain a naphtholic hydroxy group conjugated with the azo linkage exist in aqueous solution as an equilibrium mixture of two chemically distinct tautomers, the azo or hydrazone forms (Oakes, 2002). It is suggested that in a real azo compound the N=N double bond should have a length of 1.20–1.28 Å and the bond length of N–N single bonds, as in hydrazone tautomers, should be more than 1.4 Å. In the title compound, N–N bond lengths are 1.287 Å for N1–N2 , between the suggested N=N double bond and N–N single bond lengths. In the molecule, all bond lengths are in good agreement with those reported for other azo compounds (Yazıcı et al., 2010; Karadayı et al., 2006). We report here in the crystal structure of the title compound, obtained through the diazotization of 4-tert-butyl-2-hydroxy aniline followed by a coupling reaction with 2-naphthol.
The molecule of the title compound, with the atom numbering scheme, is shown in Fig. 1, crystallizes in the monoclinic space group P21/m. The molecular structure C20H20N2O2 is shown in Figure 1 The molecule adopts an anti–configuration with the two aryl groups reside on the opposite side of azo–group. The intramolecular N—H···O hydrogen bond is found (Table 1). In the crystal molecules are linked by the weak C—H···O interactions into chains.