Crystal Structure of an Anthraquinone Dye, C.I. Disperse Violet 27

Abstract

The title compound, 1-anilino-4-hydroxyanthraquinone (Fig. 1), has been developed and used as an anthraquinone dyestuff called C.I. (Color Index) Disperse Violet 27 (C.I. 60724). 1,2 Despite the commercial significance of this dye class, a search of the literature suggested that the crystal structures of the anthraquinone dyes had not been published. With these points in mind, this paper presents the results of an X-ray analysis of the title compound during the course of our investigation concerning the structures and properties of disperse dyes. The disperse dye used was purchased from Clariant Co. Single crystals suitable for X-ray crystallography were prepared by recrystallization from toluene. The crystal and experimental data are given in Table 1. The structure was solved by direct methods and refined with anisotropic temperature factors for non-hydrogen atoms. All hydrogen atoms were located from difference Fourier maps and were not refined. The atomic coordinates for non-hydrogen atoms are listed in Table 2. The selected bond lengths and bond 1355

X-ray crystal structure of C.I. Disperse Brown 1

“…Accordingly, the technical performance and functionality of the disperse dyes have strong relationship with their particle size, morphology as well as crystal structure arrangement [15]. As part of longterm program for the investigation of structure/function relationships for the dye molecules, our group has reported the crystal structures of some disperse dyes such as monoazo [11], methine [12] and anthraquinone [13] dyes. Recently we were successful to prepare the single crystals of C.I.…”

Single crystal X-ray structure of C.I. Disperse Yellow 3

“…860 (4) 7683 (2) 1039 (2) 22(1) C(4) À121(4) 8571 (3) 1279 (2) 27(1) C (5) 108 (4) 9262 (3) 2169 (2) 26(1) C (6) 1355 (4) 9076 (2) 2849 (2) 23(1) C (7) 2335 (4) 8209 (3) 2617 (2) 24(1) C (8) 2097 (4) 7494 (3) 1719 (2) 25(1) C (9) 1047 (4) 11228 (3) 4878 (2) 24(1) C(10) 5(4) 12091 (3) 5061 (2) 26(1) C (11) 185 (4) 12863 (3) 5925 (2) 26(1) C (12) 1439 (4) 12738 (3) 6630 (2) 29(1) C (13) 2492 (4) 11898 (3) 6470 (2) 31(1) C (14) 2327 (4) the acetonitrile solution of the purified dye after two weeks of storage in a refrigerator. The crystal used exists in the triclinic space group P-1.…”

“…As part of a research study concerning the structure/function relationships of dye molecules, we have reported the crystal structures of several types of disperse dyes such as monoazo [12,13], methine [14] and anthraquinone [15] classes. As a continuation of this research, we describe herein the crystal structure of C.I.…”

Crystal structures of C.I. Disperse Red 65 and C.I. Disperse Red 73

“…Furthermore, the demand for the development of new functional dyes also requires additional information including the structural conformations of already existing dyestuff in molecular level. As a part of research program for the structure/function relationships of the dye molecules, we have reported the crystal structures of several types of disperse dyes such as monoazo [12][13][14], methine [15] and anthraquinone [16] dyes. In particular, disperse azo dyes have been continuously used in the paper, foodstuffs and leather as well as textile industry [1].…”