The crystal structure of methyl orange monohydrate monoethanolate

Hanson, A. W.

doi:10.1107/s0567740873002748

Cited by 29 publications

(14 citation statements)

References 4 publications

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“…The N(1)--N(2), C(4)--N(1) and N(2)--C(9) bond lengths indicate that the compound exists as the azo tautomer. The S--O distances are almost equal and have values similar to those found for methylorange (Hanson, 1973). The dihedral angles between the phenyl rings are 11.2 (1) for (I) and 8.…”

supporting

confidence: 57%

4-(4-Hydroxy-3,5-dimethylphenylazo)benzenesulfonic Acid

Ehlinger¹,

Perrin²

1995

Acta Crystallogr C

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O(1)----C(7) 1.218 (8) C(1)---C(2) 1.516 (9) O(2)----C(8)1.231 (8)Intensities were corrected for Lorentz and polarization effects. The structure was solved by direct methods using MITHRIL (Gilmore, 1984 NOELLE EHLINGER AND MONIQUE PERRIN 1847 1993). The properties of these azocalixarenes are often compared with those of their non-cyclic analogues (Shinkai et al., 1989;Nomura, Taniguchi & Tamura, 1989;Nomura, Taniguchi & Otsuji, 1993). It is for this purpose that we describe here the crystal structure of 4-(3,5-dimethyl-4-hydroxyphenylazo)benzenesulfonic acid. The crystallization of this product gives two kinds of crystals of the monohydrate: cubes (I) and needles (II). In (I), intermolecular hydrogen bonds have been found between the water molecule and 0(2) and 0(4) of two sulfonic groups, and O(1) of the hydroxy group. There is also a bifurcated hydrogen bond between N(2) and two O atoms [0(2) and 0(4)] of two sulfonic groups, an H atom being located at 0.959/~ from N(2). This interaction corresponds to a charge-transfer interaction because a proton was transferred from the sulfonic group to N(2) of the azo group. MeIn (II), intermolecular hydrogen bonds have been found between the water molecule and 0(3) and 0(4) of two sulfonic groups, and O(1) of the hydroxyl group. We also find a fourth interaction between N(2) and 0(2) which corresponds to a charge-transfer interaction, the H atom being located at 0.945/~, from N(2).A-5-Z. ExperimentalThe title compound was prepared by a diazo coupling reaction of 2,6-dimethylphenol and diazoted sodium sulfanilate in water at ca 275 K. At the end of the reaction, the red solution was treated with hydrochloric acid and p-(4-hydroxy-3,5-dimethylphenylazo)benzenesulfonic acid was isolated by filtration and recrystallized from water (63% yield). IH NMR (D20): 6 2.18 (6H, s, CH3), 7.43 (2H, s, ArH in the phenol moiety), 7.70 and 7.87 p.p.m. (both 2H, d, ArH in the 4-sulfonic phenyl moiety). Elemental analysis: calculated for Cn4HI4N204S.H20, C 51.84, H 4.97, N 8.64, S 9.88%; found, C 51.70, H 4.91, N 8.66, S 9.89%. Form (I) Crystal dataCI4Hi4N204S.H20 NOELLE EHLINGER AND MONIQUE PERRIN 18492.541 (4) 151 ( -177.9 In both structures, H atoms bonded to C atoms were placed in calculated positions. H atoms bonded to N atoms and O atoms were located in difference maps. ©1995 International Union of CrystallographyPrinted in Great Britain -all rights reserved AbstractIn the molecule of the title compound, C15H1502P, the C==C--~ fragment has an S-cis conformation. The methoxyphenyl ring assumes an almost coplanar arrangement with the ~ bond and is almost perpendicular to the phenyl ring.

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confidence: 57%

4-(4-Hydroxy-3,5-dimethylphenylazo)benzenesulfonic Acid

Ehlinger¹,

Perrin²

1995

Acta Crystallogr C

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“…1 showing a view of the molecules with the numbering of the atoms was drawn by PLUTO78 (Motherwell & Clegg, 1978). (4) 6845 (3) 11820 (5) 332 (5) 0.07 1180 (3) 8599 (6) 7116 (5) C (5) 6314 (3) 11366 (5) 1009 (5) 0.06 972 (3) 8104 (5) 5642 (4) C (6) 6341 (2) 9924 (4) 660 (4) 0.05 89 (3) 8310 (4) 5042 (4) N (7) 5792 (2) 9386 (4) 1268 (4) (17) 6424 (1) 6005 (1) 460 (1) 0.06 8114 (1) 5902 (1) 4869 (1) O (1) 7894 (2) 7787 (3) 2958 (3) 0.06 5500 (2) 15687 (3) 7267 (4) 0(2) 3822 (2) 14744 (4) The N(7)--N(8) bond distance (1.313 A) in the two molecules is longer than in other azobenzene structures (average value 1.23 A) (Brown, 1966a,b;Kakati & Chaudhuri, 1968;Hope & Victor, 1969;Gilardi & Karle, 1972;Hanson, 1973;Graeber & Morosin, 1974;Kuvosaki, Kashino & Haisa, 1976;Vani & Vijayan, 1977;Moreiras, Solans, Solans, Miravitlles, Germain & Declercq, 1980), while it is shorter than the N-N single-bond distance (1.44 A) (International Tables for X- All these bond-length variations are consistent with an electronic resonance for the protonated 2,4-diaminoazobenzene cation with the canonical forms shown in Fig. 3.…”

Section: Germainmentioning

confidence: 99%

2,4-Diaminoazobenzene hydrochloride dihydrate (chrysoidine S.L.)

Moreiras¹,

Solans²,

Soláns³

et al. 1981

Acta Crystallogr Sect B

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“…The title compound shows a layered structure in which Mn(H 2 O) 6 inorganic layers are located between the organic (anion of "methyl orange") bilayers. Many crystal structures related with methyl orange are reported so far [5][6][7][8]. The hydrogen bonds which connect the Mn(H 2 O) 6 with the organic anion result in a layer in the ab plane.…”

Section: Discussionmentioning

confidence: 99%

“…In this structure, the C-N bond lengths are shorter than the sum of the single-bond covalent radii, 1.47 Å (N1-C4 = 1.424 Å, N2-C7 = 1.423 Å, N3-C10 = 1.368 Å). This is explained by a 'sacri cial' structure [5,10,11].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of hexaaquamanganese(II) bis((E)-4-((4-(dimethylamino)phenyl)diazenyl)benzenesulfonate), C₂₈H₄₀MnN₆O₁₂S₂

Park

2016

Zeitschrift Für Kristallographie - New Crystal Structures

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C 28 H 40 MnN 6 O 12 S 2 , monoclinic, P21/c (no. 14), a = 6.211(5) Å, CCDC no.: 1446507The crystal structure is shown in the gure. Tables 1-3 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters. Source of materialMnCl 2 . 4H 2 O (0.2976 g) was added to a solution of C14H14N 3 NaO 3 S (0.491 g) in methanol (200 mL) and the mixture was slowly evaporated. Small red-brown crystals were obtained approximately after a week. Experimental detailsAll H atoms were located in a di erence Fourier map. Carbon-bound hydrogen atoms are riding on the parent atom, whereas the oxygen-bound hydrogen atom positions are re ned. H atoms at methyl group were re ned with U iso (H) = 1.5Ueq(C).

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The crystal structure of methyl orange monohydrate monoethanolate

Cited by 29 publications

References 4 publications

4-(4-Hydroxy-3,5-dimethylphenylazo)benzenesulfonic Acid

4-(4-Hydroxy-3,5-dimethylphenylazo)benzenesulfonic Acid

2,4-Diaminoazobenzene hydrochloride dihydrate (chrysoidine S.L.)

Crystal structure of hexaaquamanganese(II) bis((E)-4-((4-(dimethylamino)phenyl)diazenyl)benzenesulfonate), C₂₈H₄₀MnN₆O₁₂S₂

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The crystal structure of methyl orange monohydrate monoethanolate

Cited by 29 publications

References 4 publications

4-(4-Hydroxy-3,5-dimethylphenylazo)benzenesulfonic Acid

4-(4-Hydroxy-3,5-dimethylphenylazo)benzenesulfonic Acid

2,4-Diaminoazobenzene hydrochloride dihydrate (chrysoidine S.L.)

Crystal structure of hexaaquamanganese(II) bis((E)-4-((4-(dimethylamino)phenyl)diazenyl)benzenesulfonate), C28H40MnN6O12S2

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Crystal structure of hexaaquamanganese(II) bis((E)-4-((4-(dimethylamino)phenyl)diazenyl)benzenesulfonate), C₂₈H₄₀MnN₆O₁₂S₂