organic compounds
(4-Aminosulfonylphenyl)[(2-oxidonaphthalen-1-yl)imino]azanium
aUnité de Recherche de Chimie de l'Environnement, et Moléculaire Structurale, Faculté du sciences exactes, Université des Fréres Mentouri 1, 25000 Constantine, Algeria
*Correspondence e-mail: king.ali@hotmail.fr
The 16H13N3O3S, shows that the two independent in the are approximately planar. Intramolecular N—H⋯O hydrogen bonds occur and the aromatic rings have a trans configuration with respect to the azo double bond. In the crystal, the molecules are linked via N—H⋯O hydrogen bonds and π–π stacking, forming a three-dimensional supramolecular network, the π–π stacking interactions between adjacent benzene and naphthalene rings having centroid-to-centroid distances of 3.764 (3) and 3.775 (3) Å.
of the title compound, CKeywords: crystal structure; β-naphthol; hydrogen bonding; π–π stacking.
CCDC reference: 1474796
Structure description
Dyes are natural or synthetic coloured chemical compounds. Usually organic in nature, they have the ability to permanently stain the material to which they are applied. Azo pigments are widely used for the colouration of coatings, plastics and printing inks, with an annual sales volume of more than one billion Euros (Biswas & Umapathy, 2000). In the literature, most azo pigments are drawn with an N=N double bond (Olivieri et al., 1989). However, all commercial pigments based on β-naphthol adopt the hydrazone tautomeric form in the solid state, as proven by many X-ray structure determinations of β-naphthol pigments.
There are two independent molecules (A and B) in the of the title compound (Fig. 1), each consisting of a benzene ring linked to the first nitrogen atom of the N=N chromophore and two aromatic rings of the core β-naphthol. The aromatic rings are in a trans configuration with respect to the azo double bond. The N1—C1 (molecule A) and N4—C17 (molecule B) bond lengths of 1.398 (3) and 1.393 (3) Å, respectively, indicate single-bond character. The N2—C7 (molecule A) and N5—C23 (molecule B) bond lengths of 1.332 (3) and 1.331 (3) Å, and the N=N bond lengths of 1.313 (3) and 1.315 (3) Å in molecules A and B, respectively, are indicative of significant double-bond character.
In the crystal, the A and B molecules are linked via N—H⋯O hydrogen bonds, forming zigzag –A–B–A–B– chains propagating along the b axis (see Table 1 and Fig. 2). The chains are reinforced by π–π interactions, forming a three-dimensional network; see Fig. 3 [Cg1⋯Cg6i = 3.775 (3) Å, where Cg1 and Cg6 are the centroids of rings C1–C6 and C23–C28, respectively; symmetry code: (i) x, − y, − + z].
Synthesis and crystallization
For synthesis details, see: Jin et al. (2008); Lee et al. (2004). A mixture of 4-aminobenzenesulonamide (0.02 mol), water (40 ml) and concentrated hydrochloric acid (0.06 mol) was stirred. This solution was cooled to 273–278 K and a solution of sodium nitrite (0.02 mol) in water (10 ml) was added dropwise, while maintaining the temperature below 278 K. The resulting mixture was stirred for an additional 30 min in an ice bath and then buffered with solid sodium acetate. β-Naphthol (0.02 mol), dissolved with sodium hydroxide (0.02 mol) in water (10 ml), was cooled to 273–278 K in an ice bath and then gradually added to the above solution of 4-sulfamoylbenzenediazonium. The resulting mixture was stirred for 60 min. The crude precipitate was filtered off, washed several times with water and recrystallized from methanol. The compound was recrystallized from methanol to produce crystals of suitable quality for X-ray diffraction analysis.
IR spectroscopic data (ν, cm−1): 3433.1 (O—H), 1616 (C=O), 3745 (O_H) and 1496 (Ar). UV–Vis measurements [λ (nm), log ∊ (l/mol cm), CH2Cl2]: 308.8 (0.093), 477.86 (0.203). 1H NMR [500 MHz, DMSO-10 (1D 1H), σ]: 16 (s, 1H, NH), 740–7.85 (m, 10H, Ar), 2.29 (s, 3H, CH 3). 13C NMR [500 MHz, DMSO-11(1D 13 C), σ]: 177(C=O), 115(C=N), 144(C—N), 125(C aromatic).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 1474796
10.1107/S2414314616006581/xu4006sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616006581/xu4006Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616006581/xu4006Isup3.cml
For synthesis details, see: Jin et al. (2008); Lee et al. (2004). A mixture of 4-aminobenzenesulonamide (0.02 mol), water (40 ml) and concentrated hydrochloric acid (0.06 mol) was stirred. This solution was cooled to 273–278 K and a solution of sodium nitrite (0.02 mol) in water (10 ml) was added dropwise, while maintaining the temperature below 278 K. The resulting mixture was stirred for an additional 30 min in an ice bath and then buffered with solid sodium acetate. β-Naphthol (0.02 mol), dissolved with sodium hydroxide (0.02 mol) in water (10 ml), was cooled to 273–278 K in an ice bath and then gradually added to the above solution of 4-sulfamoylbenzenediazonium. The resulting mixture was stirred for 60 min. The crude precipitate was filtered off, washed several times with water and recrystallized from methanol. The compound was recrystallized from methanol to produce crystals of suitable quality for X-ray diffraction analysis.
The IR spectrum was recorded using an Shimatzu FTIR 8000 spectrophotometer. IR spectroscopic data (ν, cm-1): 3433.1 (O—H), 1616 (C═O), 3745 (O_H) and 1496 (Ar). UV–Vis measurements [λ (nm), log ε (l/mol cm), CH2Cl2]: 308.8 (0.093), 477.86 (0.203). 1H NMR [500 MHz, DMSO-10 (1D 1H), σ]: 16 (s, 1H, NH), 740–7.85 (m, 10H, Ar), 2.29 (s, 3H, CH 3). 13C NMR [500 MHz, DMSO-11(1D 13 C), σ]: 177(C═O), 115(C═N), 144(C—N), 125(C aromatic).
Dyes are natural or synthetic coloured chemical compounds. Usually organic in nature, they have the ability to permanently stain the material to which they are applied. Azo pigments are widely used for the colouration of coatings, plastics and printing inks, with an annual sales volume of more than one billion Euros (Biswas & Umapathy, 2000). In the literature, most azo pigments are drawn with an N═N double bond (Olivieri et al., 1989). However, all commercial pigments based on β-naphthol adopt the hydrazone tautomeric form in the solid state, as proven by many X-ray structure determinations of β-naphthol pigments.
There are two independent molecules (A and B) in the ═N chromophore and two aromatic rings of the core β-naphthol. The aromatic rings are in a trans configuration with respect to the azo double bond. The N1—C1 (molecule A) and N4—C17 (molecule B) bond lengths of 1.398 (3) and 1.393 (3) Å, respectively, indicate single-bond character. The N2—C7 (molecule A) and N5—C23 (molecule B) bond lengths of 1.332 (3) and 1.331 (3) Å, and the N═N bond lengths of 1.313 (3) and 1.315 (3) Å in molecules A and B, respectively, are indicative of significant double-bond character.
of the title compound (Fig. 1), each consisting of a benzene ring linked to the first nitrogen atom of the NIn the crystal, the A and B molecules are linked via N—H···O hydrogen bonds, forming zigzag –A–B–A–B– chains propagating along the b axis (see Table 1 and Fig. 2). The chains are reinforced by π–π interactions, forming a three-dimensional network; see Fig. 3 [Cg1···Cg6i = 3.775 (3) Å, where Cg1 and Cg6 are the centroids of rings C1–C6 and C23–C28, respectively; symmetry code: (i) x, 1/2 - y, -1/2 + z].
Data collection: APEX2 (Bruker, 2006); cell
APEX2 (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).Fig. 1. The asymmetric unit of the two independent molecules with 50% probability displacement ellipsoids and H atoms are drawn as small spheres of arbitrary radii. Atom labels should not overlap atoms or bonds | |
Fig. 2. A view along the b axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines and C-bound H atoms not involved in hydrogen bonding have been omitted for clarity. | |
Fig. 3. The packing of viewed along [010]. π–π interactions are shown as dashed lines, and C-bound H atoms not involved in hydrogen bonding have been omitted for clarity. |
C16H13N3O3S | F(000) = 1360 |
Mr = 327.35 | Dx = 1.483 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5463 reflections |
a = 26.289 (5) Å | θ = 2.9–25.4° |
b = 15.132 (5) Å | µ = 0.24 mm−1 |
c = 7.403 (5) Å | T = 293 K |
β = 95.179 (5)° | Needle, colourless |
V = 2933 (2) Å3 | 0.09 × 0.04 × 0.02 mm |
Z = 8 |
Enraf–Nonius FR590 CCD diffractometer | 3577 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Horizonally mounted graphite crystal monochromator | θmax = 25.4°, θmin = 3.1° |
Detector resolution: 9 pixels mm-1 | h = −31→31 |
CCD rotation images, thick slices scans | k = −18→15 |
8680 measured reflections | l = −8→8 |
5356 independent reflections |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0514P)2 + 0.988P] where P = (Fo2 + 2Fc2)/3 |
5356 reflections | (Δ/σ)max = 0.001 |
415 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C16H13N3O3S | V = 2933 (2) Å3 |
Mr = 327.35 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 26.289 (5) Å | µ = 0.24 mm−1 |
b = 15.132 (5) Å | T = 293 K |
c = 7.403 (5) Å | 0.09 × 0.04 × 0.02 mm |
β = 95.179 (5)° |
Enraf–Nonius FR590 CCD diffractometer | 3577 reflections with I > 2σ(I) |
8680 measured reflections | Rint = 0.031 |
5356 independent reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.23 e Å−3 |
5356 reflections | Δρmin = −0.34 e Å−3 |
415 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 | ||
S1 | 0.52672 (2) | 0.13841 (4) | 0.47978 (9) | 0.0426 (2) | |
O1 | 0.81398 (8) | 0.14154 (13) | 0.9633 (3) | 0.0613 (8) | |
O2 | 0.52403 (7) | 0.22982 (12) | 0.4290 (3) | 0.0576 (7) | |
O3 | 0.50989 (7) | 0.07261 (12) | 0.3487 (2) | 0.0521 (7) | |
N1 | 0.73795 (8) | 0.06996 (14) | 0.7901 (3) | 0.0455 (8) | |
N2 | 0.76294 (8) | −0.00485 (14) | 0.7818 (3) | 0.0409 (7) | |
N3 | 0.49191 (8) | 0.12714 (14) | 0.6468 (3) | 0.0459 (8) | |
C1 | 0.68829 (10) | 0.08099 (17) | 0.7085 (3) | 0.0411 (9) | |
C2 | 0.65908 (9) | 0.01275 (17) | 0.6299 (3) | 0.0416 (9) | |
C3 | 0.60995 (10) | 0.03003 (17) | 0.5570 (3) | 0.0421 (9) | |
C4 | 0.59032 (9) | 0.11517 (16) | 0.5609 (3) | 0.0393 (8) | |
C5 | 0.61962 (11) | 0.18314 (18) | 0.6383 (4) | 0.0539 (10) | |
C6 | 0.66842 (11) | 0.16604 (18) | 0.7132 (4) | 0.0550 (10) | |
C7 | 0.81068 (10) | −0.00709 (17) | 0.8590 (3) | 0.0401 (9) | |
C8 | 0.83656 (10) | 0.06915 (19) | 0.9463 (4) | 0.0467 (10) | |
C9 | 0.88915 (11) | 0.0587 (2) | 1.0144 (4) | 0.0538 (11) | |
C10 | 0.91382 (11) | −0.0178 (2) | 0.9982 (4) | 0.0540 (10) | |
C11 | 0.89000 (10) | −0.0945 (2) | 0.9151 (3) | 0.0464 (9) | |
C12 | 0.83819 (10) | −0.09042 (18) | 0.8461 (3) | 0.0430 (9) | |
C13 | 0.81554 (11) | −0.16598 (19) | 0.7642 (4) | 0.0504 (10) | |
C14 | 0.84370 (12) | −0.2420 (2) | 0.7496 (4) | 0.0591 (11) | |
C15 | 0.89420 (13) | −0.2463 (2) | 0.8171 (4) | 0.0640 (11) | |
C16 | 0.91724 (11) | −0.1738 (2) | 0.8993 (4) | 0.0573 (10) | |
S2 | 0.96326 (3) | 0.11985 (4) | 0.61220 (9) | 0.0431 (2) | |
O4 | 0.66722 (8) | 0.12662 (13) | 0.2014 (3) | 0.0610 (8) | |
O5 | 0.98563 (7) | 0.04127 (12) | 0.6943 (2) | 0.0502 (7) | |
O6 | 0.96294 (8) | 0.19919 (13) | 0.7176 (3) | 0.0618 (8) | |
N4 | 0.75208 (8) | 0.05467 (15) | 0.2964 (3) | 0.0473 (8) | |
N5 | 0.73576 (8) | −0.02057 (14) | 0.2236 (3) | 0.0428 (8) | |
N6 | 0.99497 (8) | 0.14091 (15) | 0.4412 (3) | 0.0488 (8) | |
C17 | 0.80156 (9) | 0.06436 (17) | 0.3787 (3) | 0.0406 (9) | |
C18 | 0.83630 (10) | −0.00473 (17) | 0.4023 (3) | 0.0430 (9) | |
C19 | 0.88533 (10) | 0.01125 (17) | 0.4784 (3) | 0.0417 (9) | |
C20 | 0.89966 (9) | 0.09626 (17) | 0.5320 (3) | 0.0394 (8) | |
C21 | 0.86483 (11) | 0.16454 (18) | 0.5132 (4) | 0.0546 (10) | |
C22 | 0.81611 (11) | 0.14848 (18) | 0.4370 (4) | 0.0557 (10) | |
C23 | 0.68820 (10) | −0.02283 (17) | 0.1450 (3) | 0.0392 (8) | |
C24 | 0.65301 (10) | 0.05225 (19) | 0.1399 (4) | 0.0462 (10) | |
C25 | 0.60133 (10) | 0.0383 (2) | 0.0648 (4) | 0.0523 (10) | |
C26 | 0.58605 (11) | −0.0409 (2) | −0.0009 (4) | 0.0523 (10) | |
C27 | 0.61932 (10) | −0.11560 (19) | −0.0043 (3) | 0.0449 (9) | |
C28 | 0.67105 (10) | −0.10720 (18) | 0.0631 (3) | 0.0415 (9) | |
C29 | 0.70359 (11) | −0.17918 (19) | 0.0507 (4) | 0.0499 (10) | |
C30 | 0.68508 (12) | −0.2588 (2) | −0.0189 (4) | 0.0579 (11) | |
C31 | 0.63398 (13) | −0.2678 (2) | −0.0781 (4) | 0.0630 (11) | |
C32 | 0.60165 (12) | −0.1976 (2) | −0.0732 (4) | 0.0567 (11) | |
H1 | 0.75520 | 0.11260 | 0.84890 | 0.0550* | |
H2 | 0.67240 | −0.04410 | 0.62630 | 0.0500* | |
H3 | 0.58990 | −0.01550 | 0.50510 | 0.0500* | |
H5 | 0.60650 | 0.24020 | 0.63980 | 0.0650* | |
H6 | 0.68820 | 0.21150 | 0.76720 | 0.0660* | |
H9 | 0.90640 | 0.10620 | 1.07100 | 0.0640* | |
H10 | 0.94800 | −0.02130 | 1.04290 | 0.0650* | |
H13 | 0.78130 | −0.16480 | 0.71940 | 0.0600* | |
H14 | 0.82830 | −0.29140 | 0.69310 | 0.0710* | |
H15 | 0.91260 | −0.29830 | 0.80680 | 0.0770* | |
H16 | 0.95130 | −0.17690 | 0.94520 | 0.0690* | |
H33 | 0.49940 | 0.16570 | 0.73690 | 0.0550* | |
H34 | 0.48950 | 0.07340 | 0.69490 | 0.0550* | |
H4 | 0.72860 | 0.09980 | 0.29010 | 0.0570* | |
H18 | 0.82650 | −0.06170 | 0.36690 | 0.0520* | |
H19 | 0.90870 | −0.03490 | 0.49380 | 0.0500* | |
H21 | 0.87430 | 0.22120 | 0.55190 | 0.0660* | |
H22 | 0.79260 | 0.19450 | 0.42430 | 0.0670* | |
H25 | 0.57810 | 0.08480 | 0.06170 | 0.0630* | |
H26 | 0.55210 | −0.04770 | −0.04650 | 0.0630* | |
H29 | 0.73810 | −0.17360 | 0.08950 | 0.0600* | |
H30 | 0.70710 | −0.30650 | −0.02590 | 0.0690* | |
H31 | 0.62160 | −0.32210 | −0.12160 | 0.0760* | |
H32 | 0.56750 | −0.20410 | −0.11590 | 0.0680* | |
H35 | 1.00100 | 0.09020 | 0.37420 | 0.0590* | |
H36 | 0.98490 | 0.18830 | 0.37420 | 0.0590* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0367 (4) | 0.0394 (4) | 0.0501 (4) | 0.0035 (3) | −0.0045 (3) | 0.0035 (3) |
O1 | 0.0557 (13) | 0.0468 (12) | 0.0784 (15) | −0.0017 (10) | −0.0108 (11) | −0.0044 (10) |
O2 | 0.0520 (12) | 0.0417 (11) | 0.0769 (14) | 0.0070 (9) | −0.0055 (10) | 0.0181 (10) |
O3 | 0.0499 (12) | 0.0551 (12) | 0.0490 (11) | 0.0023 (9) | −0.0086 (9) | −0.0075 (9) |
N1 | 0.0361 (13) | 0.0427 (13) | 0.0561 (14) | 0.0028 (10) | −0.0040 (10) | −0.0006 (11) |
N2 | 0.0352 (13) | 0.0427 (13) | 0.0448 (12) | 0.0041 (10) | 0.0032 (9) | 0.0063 (10) |
N3 | 0.0413 (13) | 0.0438 (13) | 0.0524 (14) | 0.0010 (10) | 0.0031 (10) | −0.0055 (11) |
C1 | 0.0334 (15) | 0.0434 (16) | 0.0458 (15) | 0.0005 (12) | −0.0002 (11) | 0.0017 (12) |
C2 | 0.0369 (15) | 0.0359 (14) | 0.0515 (16) | 0.0069 (12) | 0.0014 (12) | −0.0011 (12) |
C3 | 0.0383 (16) | 0.0369 (15) | 0.0502 (16) | −0.0013 (12) | −0.0003 (12) | −0.0023 (12) |
C4 | 0.0344 (14) | 0.0372 (15) | 0.0456 (15) | 0.0009 (12) | −0.0008 (11) | 0.0017 (12) |
C5 | 0.0443 (17) | 0.0354 (15) | 0.080 (2) | 0.0062 (13) | −0.0057 (15) | −0.0015 (14) |
C6 | 0.0429 (17) | 0.0374 (16) | 0.082 (2) | −0.0003 (13) | −0.0086 (15) | −0.0065 (15) |
C7 | 0.0341 (15) | 0.0482 (16) | 0.0376 (14) | 0.0003 (12) | 0.0007 (11) | 0.0055 (12) |
C8 | 0.0443 (17) | 0.0497 (18) | 0.0454 (16) | −0.0022 (14) | −0.0002 (12) | 0.0077 (13) |
C9 | 0.0454 (18) | 0.061 (2) | 0.0531 (17) | −0.0085 (15) | −0.0057 (13) | 0.0048 (15) |
C10 | 0.0346 (16) | 0.080 (2) | 0.0454 (16) | −0.0032 (16) | −0.0069 (12) | 0.0128 (16) |
C11 | 0.0357 (15) | 0.0646 (19) | 0.0390 (15) | 0.0061 (14) | 0.0032 (11) | 0.0128 (14) |
C12 | 0.0384 (15) | 0.0528 (17) | 0.0379 (14) | 0.0066 (13) | 0.0047 (11) | 0.0086 (13) |
C13 | 0.0420 (17) | 0.0536 (18) | 0.0543 (17) | 0.0081 (14) | −0.0028 (13) | 0.0010 (14) |
C14 | 0.063 (2) | 0.0536 (19) | 0.0597 (19) | 0.0130 (16) | 0.0002 (15) | −0.0014 (15) |
C15 | 0.066 (2) | 0.069 (2) | 0.0569 (19) | 0.0298 (18) | 0.0046 (16) | 0.0023 (17) |
C16 | 0.0418 (17) | 0.082 (2) | 0.0480 (17) | 0.0185 (17) | 0.0034 (13) | 0.0111 (17) |
S2 | 0.0389 (4) | 0.0396 (4) | 0.0488 (4) | −0.0031 (3) | −0.0072 (3) | −0.0020 (3) |
O4 | 0.0544 (13) | 0.0439 (12) | 0.0825 (15) | 0.0029 (10) | −0.0064 (11) | −0.0047 (11) |
O5 | 0.0459 (11) | 0.0499 (12) | 0.0525 (11) | 0.0026 (9) | −0.0089 (9) | 0.0091 (9) |
O6 | 0.0572 (13) | 0.0518 (12) | 0.0737 (14) | −0.0058 (10) | −0.0087 (10) | −0.0245 (11) |
N4 | 0.0364 (13) | 0.0413 (13) | 0.0623 (15) | −0.0011 (10) | −0.0054 (10) | −0.0037 (11) |
N5 | 0.0391 (13) | 0.0434 (13) | 0.0450 (13) | −0.0053 (10) | −0.0004 (10) | 0.0010 (10) |
N6 | 0.0440 (14) | 0.0416 (13) | 0.0604 (15) | −0.0025 (10) | 0.0028 (11) | 0.0127 (11) |
C17 | 0.0339 (15) | 0.0414 (16) | 0.0456 (15) | −0.0019 (12) | −0.0016 (11) | 0.0015 (12) |
C18 | 0.0440 (16) | 0.0358 (15) | 0.0483 (15) | −0.0073 (13) | −0.0015 (12) | −0.0035 (12) |
C19 | 0.0405 (16) | 0.0357 (14) | 0.0479 (15) | 0.0036 (12) | −0.0007 (12) | 0.0001 (12) |
C20 | 0.0389 (15) | 0.0352 (14) | 0.0427 (15) | −0.0004 (12) | −0.0044 (11) | −0.0019 (12) |
C21 | 0.0476 (18) | 0.0339 (15) | 0.079 (2) | 0.0006 (13) | −0.0131 (15) | −0.0085 (14) |
C22 | 0.0426 (18) | 0.0374 (16) | 0.084 (2) | 0.0048 (13) | −0.0113 (15) | −0.0054 (15) |
C23 | 0.0330 (15) | 0.0441 (15) | 0.0400 (14) | −0.0062 (12) | 0.0001 (11) | 0.0021 (12) |
C24 | 0.0422 (17) | 0.0487 (17) | 0.0471 (16) | 0.0011 (13) | 0.0012 (12) | 0.0039 (14) |
C25 | 0.0389 (17) | 0.062 (2) | 0.0550 (17) | 0.0062 (14) | −0.0017 (13) | 0.0024 (15) |
C26 | 0.0350 (16) | 0.072 (2) | 0.0484 (17) | −0.0020 (15) | −0.0041 (12) | 0.0029 (15) |
C27 | 0.0399 (16) | 0.0564 (17) | 0.0376 (15) | −0.0071 (14) | −0.0008 (11) | 0.0018 (13) |
C28 | 0.0391 (15) | 0.0493 (16) | 0.0362 (14) | −0.0052 (13) | 0.0045 (11) | 0.0017 (12) |
C29 | 0.0446 (17) | 0.0550 (18) | 0.0496 (17) | −0.0027 (14) | 0.0009 (13) | −0.0024 (14) |
C30 | 0.063 (2) | 0.0517 (18) | 0.0585 (19) | −0.0013 (16) | 0.0029 (15) | −0.0093 (15) |
C31 | 0.072 (2) | 0.060 (2) | 0.0562 (19) | −0.0182 (18) | 0.0014 (16) | −0.0147 (16) |
C32 | 0.0490 (18) | 0.069 (2) | 0.0502 (17) | −0.0163 (16) | −0.0067 (14) | −0.0080 (15) |
S1—O2 | 1.434 (2) | C15—C16 | 1.369 (4) |
S1—O3 | 1.432 (2) | C2—H2 | 0.9300 |
S1—N3 | 1.612 (3) | C3—H3 | 0.9300 |
S1—C4 | 1.760 (3) | C5—H5 | 0.9300 |
S2—O5 | 1.437 (2) | C6—H6 | 0.9300 |
S2—O6 | 1.432 (2) | C9—H9 | 0.9300 |
S2—N6 | 1.609 (3) | C10—H10 | 0.9300 |
S2—C20 | 1.760 (3) | C13—H13 | 0.9300 |
O1—C8 | 1.258 (4) | C14—H14 | 0.9300 |
O4—C24 | 1.258 (4) | C15—H15 | 0.9300 |
N1—C1 | 1.398 (3) | C16—H16 | 0.9300 |
N1—N2 | 1.313 (3) | C17—C18 | 1.389 (4) |
N2—C7 | 1.332 (3) | C17—C22 | 1.387 (4) |
N1—H1 | 0.8800 | C18—C19 | 1.381 (4) |
N3—H34 | 0.8900 | C19—C20 | 1.388 (4) |
N3—H33 | 0.8900 | C20—C21 | 1.379 (4) |
N4—N5 | 1.315 (3) | C21—C22 | 1.374 (4) |
N4—C17 | 1.393 (3) | C23—C24 | 1.464 (4) |
N5—C23 | 1.331 (3) | C23—C28 | 1.467 (4) |
N4—H4 | 0.9200 | C24—C25 | 1.436 (4) |
N6—H35 | 0.9300 | C25—C26 | 1.341 (4) |
N6—H36 | 0.9000 | C26—C27 | 1.431 (4) |
C1—C2 | 1.383 (4) | C27—C32 | 1.405 (4) |
C1—C6 | 1.391 (4) | C27—C28 | 1.411 (4) |
C2—C3 | 1.379 (4) | C28—C29 | 1.393 (4) |
C3—C4 | 1.389 (4) | C29—C30 | 1.382 (4) |
C4—C5 | 1.378 (4) | C30—C31 | 1.382 (5) |
C5—C6 | 1.375 (4) | C31—C32 | 1.363 (5) |
C7—C8 | 1.460 (4) | C18—H18 | 0.9300 |
C7—C12 | 1.461 (4) | C19—H19 | 0.9300 |
C8—C9 | 1.437 (4) | C21—H21 | 0.9300 |
C9—C10 | 1.338 (4) | C22—H22 | 0.9300 |
C10—C11 | 1.431 (4) | C25—H25 | 0.9300 |
C11—C12 | 1.412 (4) | C26—H26 | 0.9300 |
C11—C16 | 1.408 (4) | C29—H29 | 0.9300 |
C12—C13 | 1.402 (4) | C30—H30 | 0.9300 |
C13—C14 | 1.378 (4) | C31—H31 | 0.9300 |
C14—C15 | 1.377 (5) | C32—H32 | 0.9300 |
O1···N1 | 2.520 (3) | C17···N2 | 3.403 (4) |
O1···N2 | 2.861 (4) | C18···C12 | 3.528 (4) |
O1···C17i | 3.333 (4) | C18···C8x | 3.557 (4) |
O1···C21ii | 3.232 (4) | C18···C9x | 3.438 (4) |
O1···C22ii | 3.184 (4) | C18···C7 | 3.507 (4) |
O2···N3iii | 3.073 (4) | C19···C7 | 3.587 (4) |
O3···O3iv | 3.214 (3) | C19···C9x | 3.520 (4) |
O3···N3iv | 3.023 (3) | C19···C12 | 3.453 (4) |
O3···C25 | 3.373 (4) | C19···C11 | 3.599 (4) |
O4···C5iii | 3.157 (4) | C21···O1iii | 3.232 (4) |
O4···N4 | 2.525 (3) | C22···O1iii | 3.184 (4) |
O4···C6iii | 3.139 (4) | C23···C1x | 3.593 (4) |
O4···N5 | 2.860 (4) | C23···N1x | 3.347 (4) |
O5···C10 | 3.192 (4) | C24···C3 | 3.400 (4) |
O5···N6v | 2.993 (4) | C24···C1x | 3.433 (4) |
O5···C10vi | 3.348 (4) | C25···O3 | 3.373 (4) |
O6···N6ii | 3.009 (4) | C26···C3x | 3.554 (4) |
O1···H1 | 1.7500 | C26···C2x | 3.573 (4) |
O1···H21ii | 2.6600 | C27···C2x | 3.565 (4) |
O1···H22ii | 2.5500 | C28···C31ix | 3.471 (5) |
O2···H33iii | 2.1900 | C29···C31ix | 3.529 (5) |
O2···H5 | 2.5600 | C29···C30ix | 3.399 (5) |
O3···H3 | 2.6700 | C30···C29viii | 3.399 (5) |
O3···H26vii | 2.6700 | C31···C28viii | 3.471 (5) |
O3···H34iv | 2.2300 | C31···C29viii | 3.529 (5) |
O3···H25 | 2.9100 | C8···H1 | 2.2900 |
O4···H4 | 1.7300 | C16···H15ix | 3.0600 |
O4···H6iii | 2.5500 | C24···H4 | 2.3000 |
O4···H5iii | 2.5900 | C27···H31ix | 2.9800 |
O5···H19 | 2.6600 | C28···H31ix | 2.9700 |
O5···H35v | 2.0900 | H1···O1 | 1.7500 |
O5···H10vi | 2.5100 | H1···H6 | 2.3500 |
O6···H21 | 2.5600 | H1···C8 | 2.2900 |
O6···H36ii | 2.1100 | H2···N2 | 2.6200 |
N1···O1 | 2.520 (3) | H3···O3 | 2.6700 |
N1···C23i | 3.347 (4) | H3···N3iv | 2.8800 |
N2···O1 | 2.861 (4) | H3···H34iv | 2.6000 |
N2···C17 | 3.403 (4) | H4···O4 | 1.7300 |
N3···O2ii | 3.073 (4) | H4···C24 | 2.3000 |
N3···O3iv | 3.023 (3) | H4···H22 | 2.3600 |
N4···O4 | 2.525 (3) | H5···O2 | 2.5600 |
N5···O4 | 2.860 (4) | H5···O4ii | 2.5900 |
N6···O5v | 2.993 (4) | H6···O4ii | 2.5500 |
N6···O6iii | 3.009 (4) | H6···H1 | 2.3500 |
N2···H2 | 2.6200 | H10···O5vi | 2.5100 |
N2···H13 | 2.5200 | H10···H16 | 2.4700 |
N3···H3iv | 2.8800 | H13···N2 | 2.5200 |
N5···H29 | 2.5200 | H13···H30ix | 2.5800 |
N5···H18 | 2.6000 | H14···H18ix | 2.5700 |
C1···C23i | 3.593 (4) | H14···H29ix | 2.4800 |
C1···C24i | 3.433 (4) | H15···C16viii | 3.0600 |
C2···C27i | 3.565 (4) | H16···H10 | 2.4700 |
C2···C26i | 3.573 (4) | H18···N5 | 2.6000 |
C3···C24 | 3.400 (4) | H18···H14viii | 2.5700 |
C3···C26i | 3.554 (4) | H19···O5 | 2.6600 |
C5···O4ii | 3.157 (4) | H21···O6 | 2.5600 |
C6···O4ii | 3.139 (4) | H21···O1iii | 2.6600 |
C7···C18 | 3.507 (4) | H22···H4 | 2.3600 |
C7···C19 | 3.587 (4) | H22···O1iii | 2.5500 |
C8···C17i | 3.410 (4) | H25···O3 | 2.9100 |
C8···C18i | 3.557 (4) | H26···H32 | 2.4600 |
C9···C18i | 3.438 (4) | H26···O3vii | 2.6700 |
C9···C19i | 3.520 (4) | H29···N5 | 2.5200 |
C10···O5 | 3.192 (4) | H29···H14viii | 2.4800 |
C10···O5vi | 3.348 (4) | H30···H13viii | 2.5800 |
C11···C19 | 3.599 (4) | H31···C27viii | 2.9800 |
C12···C18 | 3.528 (4) | H31···C28viii | 2.9700 |
C12···C19 | 3.453 (4) | H32···H26 | 2.4600 |
C14···C15viii | 3.580 (5) | H33···O2ii | 2.1900 |
C15···C16viii | 3.425 (5) | H34···O3iv | 2.2300 |
C15···C14ix | 3.580 (5) | H34···H3iv | 2.6000 |
C16···C15ix | 3.425 (5) | H35···O5v | 2.0900 |
C17···C8x | 3.410 (4) | H36···O6iii | 2.1100 |
C17···O1x | 3.333 (4) | ||
O2—S1—O3 | 119.23 (12) | C5—C6—H6 | 120.00 |
O2—S1—N3 | 106.57 (12) | C10—C9—H9 | 119.00 |
O2—S1—C4 | 107.76 (11) | C8—C9—H9 | 119.00 |
O3—S1—N3 | 106.50 (11) | C9—C10—H10 | 119.00 |
O3—S1—C4 | 108.55 (11) | C11—C10—H10 | 119.00 |
N3—S1—C4 | 107.74 (11) | C12—C13—H13 | 120.00 |
N6—S2—C20 | 108.58 (11) | C14—C13—H13 | 120.00 |
O5—S2—C20 | 108.36 (12) | C15—C14—H14 | 119.00 |
O5—S2—O6 | 119.05 (12) | C13—C14—H14 | 119.00 |
O5—S2—N6 | 105.98 (11) | C14—C15—H15 | 120.00 |
O6—S2—N6 | 106.95 (12) | C16—C15—H15 | 120.00 |
O6—S2—C20 | 107.56 (13) | C11—C16—H16 | 120.00 |
N2—N1—C1 | 122.3 (2) | C15—C16—H16 | 120.00 |
N1—N2—C7 | 117.3 (2) | C18—C17—C22 | 119.5 (2) |
N2—N1—H1 | 115.00 | N4—C17—C22 | 116.9 (2) |
C1—N1—H1 | 123.00 | N4—C17—C18 | 123.6 (2) |
H33—N3—H34 | 108.00 | C17—C18—C19 | 119.9 (2) |
S1—N3—H33 | 114.00 | C18—C19—C20 | 119.9 (2) |
S1—N3—H34 | 118.00 | S2—C20—C19 | 120.63 (19) |
N5—N4—C17 | 121.8 (2) | C19—C20—C21 | 120.3 (2) |
N4—N5—C23 | 117.4 (2) | S2—C20—C21 | 119.0 (2) |
N5—N4—H4 | 115.00 | C20—C21—C22 | 119.7 (3) |
C17—N4—H4 | 123.00 | C17—C22—C21 | 120.7 (3) |
S2—N6—H35 | 112.00 | N5—C23—C28 | 116.4 (2) |
S2—N6—H36 | 116.00 | C24—C23—C28 | 119.7 (2) |
H35—N6—H36 | 115.00 | N5—C23—C24 | 123.9 (2) |
N1—C1—C6 | 116.0 (2) | O4—C24—C23 | 121.3 (2) |
N1—C1—C2 | 123.6 (2) | O4—C24—C25 | 120.7 (3) |
C2—C1—C6 | 120.4 (2) | C23—C24—C25 | 118.0 (2) |
C1—C2—C3 | 119.2 (2) | C24—C25—C26 | 120.9 (3) |
C2—C3—C4 | 120.3 (2) | C25—C26—C27 | 123.3 (3) |
S1—C4—C5 | 118.08 (19) | C26—C27—C32 | 121.4 (3) |
S1—C4—C3 | 121.43 (19) | C28—C27—C32 | 119.0 (3) |
C3—C4—C5 | 120.4 (2) | C26—C27—C28 | 119.6 (3) |
C4—C5—C6 | 119.6 (2) | C23—C28—C29 | 122.7 (2) |
C1—C6—C5 | 120.2 (3) | C27—C28—C29 | 119.0 (2) |
N2—C7—C12 | 116.5 (2) | C23—C28—C27 | 118.4 (2) |
N2—C7—C8 | 123.6 (2) | C28—C29—C30 | 120.6 (3) |
C8—C7—C12 | 119.8 (2) | C29—C30—C31 | 120.3 (3) |
O1—C8—C7 | 121.8 (2) | C30—C31—C32 | 120.4 (3) |
C7—C8—C9 | 117.6 (2) | C27—C32—C31 | 120.8 (3) |
O1—C8—C9 | 120.6 (3) | C17—C18—H18 | 120.00 |
C8—C9—C10 | 121.5 (3) | C19—C18—H18 | 120.00 |
C9—C10—C11 | 122.9 (3) | C18—C19—H19 | 120.00 |
C12—C11—C16 | 119.2 (3) | C20—C19—H19 | 120.00 |
C10—C11—C16 | 121.4 (2) | C20—C21—H21 | 120.00 |
C10—C11—C12 | 119.4 (3) | C22—C21—H21 | 120.00 |
C7—C12—C11 | 118.8 (2) | C17—C22—H22 | 120.00 |
C11—C12—C13 | 118.6 (3) | C21—C22—H22 | 120.00 |
C7—C12—C13 | 122.6 (2) | C24—C25—H25 | 120.00 |
C12—C13—C14 | 120.3 (3) | C26—C25—H25 | 119.00 |
C13—C14—C15 | 121.2 (3) | C25—C26—H26 | 118.00 |
C14—C15—C16 | 119.8 (3) | C27—C26—H26 | 118.00 |
C11—C16—C15 | 120.8 (3) | C28—C29—H29 | 120.00 |
C1—C2—H2 | 120.00 | C30—C29—H29 | 120.00 |
C3—C2—H2 | 120.00 | C29—C30—H30 | 120.00 |
C2—C3—H3 | 120.00 | C31—C30—H30 | 120.00 |
C4—C3—H3 | 120.00 | C30—C31—H31 | 120.00 |
C4—C5—H5 | 120.00 | C32—C31—H31 | 120.00 |
C6—C5—H5 | 120.00 | C27—C32—H32 | 120.00 |
C1—C6—H6 | 120.00 | C31—C32—H32 | 120.00 |
O2—S1—C4—C3 | −155.6 (2) | C10—C11—C12—C7 | 1.1 (3) |
O2—S1—C4—C5 | 28.0 (2) | C10—C11—C12—C13 | 179.6 (2) |
O3—S1—C4—C3 | −25.2 (2) | C16—C11—C12—C7 | −178.4 (2) |
O3—S1—C4—C5 | 158.4 (2) | C12—C11—C16—C15 | 0.5 (4) |
N3—S1—C4—C3 | 89.8 (2) | C16—C11—C12—C13 | 0.2 (4) |
N3—S1—C4—C5 | −86.7 (2) | C10—C11—C16—C15 | −179.0 (3) |
O6—S2—C20—C19 | −158.62 (19) | C11—C12—C13—C14 | −0.9 (4) |
O5—S2—C20—C19 | −28.7 (2) | C7—C12—C13—C14 | 177.6 (3) |
O5—S2—C20—C21 | 155.0 (2) | C12—C13—C14—C15 | 1.1 (4) |
N6—S2—C20—C21 | −90.3 (2) | C13—C14—C15—C16 | −0.5 (5) |
O6—S2—C20—C21 | 25.1 (2) | C14—C15—C16—C11 | −0.3 (5) |
N6—S2—C20—C19 | 86.0 (2) | N4—C17—C18—C19 | 177.3 (2) |
C1—N1—N2—C7 | 177.7 (2) | C22—C17—C18—C19 | −1.9 (4) |
N2—N1—C1—C2 | 7.4 (4) | N4—C17—C22—C21 | −177.5 (3) |
N2—N1—C1—C6 | −174.0 (2) | C18—C17—C22—C21 | 1.8 (4) |
N1—N2—C7—C8 | −1.8 (4) | C17—C18—C19—C20 | 0.4 (3) |
N1—N2—C7—C12 | −179.1 (2) | C18—C19—C20—S2 | −174.83 (18) |
C17—N4—N5—C23 | −178.7 (2) | C18—C19—C20—C21 | 1.4 (4) |
N5—N4—C17—C18 | −4.6 (4) | S2—C20—C21—C22 | 174.7 (2) |
N5—N4—C17—C22 | 174.6 (2) | C19—C20—C21—C22 | −1.6 (4) |
N4—N5—C23—C24 | −1.8 (4) | C20—C21—C22—C17 | 0.0 (4) |
N4—N5—C23—C28 | 179.4 (2) | N5—C23—C24—O4 | 4.6 (4) |
C6—C1—C2—C3 | −0.3 (4) | N5—C23—C24—C25 | −174.5 (2) |
N1—C1—C6—C5 | −179.2 (3) | C28—C23—C24—O4 | −176.7 (2) |
N1—C1—C2—C3 | 178.3 (2) | C28—C23—C24—C25 | 4.2 (4) |
C2—C1—C6—C5 | −0.5 (4) | N5—C23—C28—C27 | 173.3 (2) |
C1—C2—C3—C4 | 0.7 (3) | N5—C23—C28—C29 | −6.2 (4) |
C2—C3—C4—C5 | −0.3 (4) | C24—C23—C28—C27 | −5.6 (3) |
C2—C3—C4—S1 | −176.65 (18) | C24—C23—C28—C29 | 174.9 (2) |
S1—C4—C5—C6 | 176.0 (2) | O4—C24—C25—C26 | 180.0 (3) |
C3—C4—C5—C6 | −0.5 (4) | C23—C24—C25—C26 | −0.9 (4) |
C4—C5—C6—C1 | 0.9 (4) | C24—C25—C26—C27 | −1.1 (5) |
N2—C7—C12—C11 | 175.8 (2) | C25—C26—C27—C28 | −0.4 (4) |
N2—C7—C12—C13 | −2.7 (4) | C25—C26—C27—C32 | 179.5 (3) |
C8—C7—C12—C11 | −1.6 (3) | C26—C27—C28—C23 | 3.7 (3) |
C8—C7—C12—C13 | 179.9 (3) | C26—C27—C28—C29 | −176.8 (2) |
C12—C7—C8—O1 | −178.6 (2) | C32—C27—C28—C23 | −176.2 (2) |
N2—C7—C8—O1 | 4.2 (4) | C32—C27—C28—C29 | 3.3 (4) |
N2—C7—C8—C9 | −176.3 (2) | C26—C27—C32—C31 | 179.0 (3) |
C12—C7—C8—C9 | 0.9 (4) | C28—C27—C32—C31 | −1.1 (4) |
O1—C8—C9—C10 | 179.8 (3) | C23—C28—C29—C30 | 176.6 (3) |
C7—C8—C9—C10 | 0.3 (4) | C27—C28—C29—C30 | −2.9 (4) |
C8—C9—C10—C11 | −0.8 (5) | C28—C29—C30—C31 | 0.4 (4) |
C9—C10—C11—C16 | 179.6 (3) | C29—C30—C31—C32 | 1.9 (5) |
C9—C10—C11—C12 | 0.1 (4) | C30—C31—C32—C27 | −1.5 (4) |
Symmetry codes: (i) x, y, z+1; (ii) x, −y+1/2, z+1/2; (iii) x, −y+1/2, z−1/2; (iv) −x+1, −y, −z+1; (v) −x+2, −y, −z+1; (vi) −x+2, −y, −z+2; (vii) −x+1, −y, −z; (viii) x, −y−1/2, z−1/2; (ix) x, −y−1/2, z+1/2; (x) x, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.88 | 1.75 | 2.520 (3) | 145 |
N3—H33···O2ii | 0.89 | 2.19 | 3.073 (4) | 172 |
N3—H34···O3iv | 0.89 | 2.23 | 3.023 (3) | 147 |
N4—H4···O4 | 0.92 | 1.73 | 2.525 (3) | 142 |
N6—H35···O5v | 0.93 | 2.09 | 2.993 (4) | 162 |
N6—H36···O6iii | 0.90 | 2.11 | 3.009 (4) | 179 |
Symmetry codes: (ii) x, −y+1/2, z+1/2; (iii) x, −y+1/2, z−1/2; (iv) −x+1, −y, −z+1; (v) −x+2, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.88 | 1.75 | 2.520 (3) | 145 |
N3—H33···O2i | 0.89 | 2.19 | 3.073 (4) | 172 |
N3—H34···O3ii | 0.89 | 2.23 | 3.023 (3) | 147 |
N4—H4···O4 | 0.92 | 1.73 | 2.525 (3) | 142 |
N6—H35···O5iii | 0.93 | 2.09 | 2.993 (4) | 162 |
N6—H36···O6iv | 0.90 | 2.11 | 3.009 (4) | 179 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z+1; (iii) −x+2, −y, −z+1; (iv) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H13N3O3S |
Mr | 327.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 26.289 (5), 15.132 (5), 7.403 (5) |
β (°) | 95.179 (5) |
V (Å3) | 2933 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.09 × 0.04 × 0.02 |
Data collection | |
Diffractometer | Enraf–Nonius FR590 CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8680, 5356, 3577 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.603 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.124, 1.06 |
No. of reflections | 5356 |
No. of parameters | 415 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.34 |
Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL2015 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), PLATON (Spek, 2009).
Acknowledgements
We gratefully acknowledge all researchers of the CHEMS Research Unit of the University Freres Mentouri of Constantine 1, Algeria, for the valuable assistance they have provided us throughout the realisation of this work.
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The dyes are chemical compounds colored natural or synthetic. Usually organic in nature, they have the ability to permanently stain the material in which they are applied. Azo pigments are widely used for the colouration of coatings, plastics and printing inks, with an annual sales volume of more than one billion Euros (Biswas & Umapathy, 2000). In the literature, most azo pigments are drawn with an N=N double bond (see scheme) (Olivieri et al., 1989). However, all commercial pigments based on β-naphthol adopt the hydrazone tautomeric form in the solid state, as proven by many X-ray structure determinations of β-naphthol pigments. This molecule consists of a benzene ring linked to the first nitrogen atom of the N=N chromophore and two aromatic rings of the core β-naphthol. The aromatic rings are in a trans configuration with respect to the azo double bond. The N1—C1 (molecule A) and N4—C17 (molecule B) bond lengths of 1.398 and 1.393 Å , respectively, indicate single-bond character. The N2—C7 (molecule A) and N5—C23 (molecule B) bond lengths of 1.332 and 1.331 Å, and the N=N bond length of 1.313 Å in the both molecules are indicative of significant double-bond character. The A and B molecules are linked via N—H···O hydrogen bonds, forming zigzag –A–B–A–B– chains propagating along b-axis (see Table 2 and Fig. 2). The chains are reinforced by π-π interactions, forming a three-dimensional network; see Fig. 3 [Cg1···Cg6i = 3.775 (3) Å , where Cg1 and Cg6 are the centroids of rings C1–C6 and C23–C28, respectively; symmetry code: (i) x,1/2-y,-1/2+z].