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 ANALYTICAL SCIENCES NOVEMBER 2001, VOL. 17
2001 The Japan Society for Analytical Chemistry
Instrumental Achievements
Crystal Structure of an Anthraquinone Dye, C.I. Disperse Violet 27
Il YOON,* Ki-Min PARK,* Shim Sung LEE,*

Green CHOI,** and Jeong Sook LEE**

*Department of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University,
Chinju 660-701, S. Korea
**Department of Clothing and Textiles, Gyeongsang National University, Chinju 660-701, S. Korea
(Received May 1, 2001; Accepted August 22, 2001)

To whom correspondence should be addressed.

E-mail: sslee@nongae.gsnu.ac.kr
Formula: C20H13NO3
Formula weight = 315.31
Temperature: 298 K
Crystal size: 0.40 0.16 0.08 mm
Crystal color: violet
Crystal description: plate
Crystal system: monoclinic
Space group: P21/c Z = 4
a = 12.4069(15)
b = 16.345(2)
c = 7.3352(9)
V = 1487.1(3)
3
DX = 1.408 g/cm
3
Radiation: 0.71073 (Mo K )
2 max = 56.62
Rint = 0.0399
R = 0.0571
wR = 0.1234
Goodness-of-fit = 1.027
( / )max < 0.0005
( )max = 0.338 e
3
( )min = 0.330 e
3
No. of reflections used = 3633[>2 (I)]
No. of parameters = 218
Diffractometer: Bruker SMART CCD system
Monochromator: graphite
Structure determination: SHELXTL
Refinement: full-matrix
Table 1 Crystal and experimental data

x z y Ueq
Table 2 Atomic coordinates ( 10
4
) and equivalent isotropic
displacement parameters (
2
10
3
)
Ueq = (1/3) ijUijai*aj*(aiaj).
Fig. 1 Chemical structure.
angles are summarized in Table 3. The molecular structure and
the atomic numbering are given in Fig. 2.
Both the anthraquinone and the phenyl rings are planar with
average deviations of 0.051 and 0.004 , respectively, from the
least-squares planes defined by all non-hydrogen atoms. The
dihedral angle between the two ring systems is 44.94(5). The
molecules are stacked by - interaction and the resulting
packing structure is a column of molecules. The intermolecular
O(2)HC(9)
i
(i: x + 1, y + 1/2 1, z + 1/2) [3.244(2)]
hydrogen bonds between the column structures formed also
stabilized the molecular packing.
Acknowledgements
The support of the Korea Research Foundation (Project No. 99-
005-D00004) is gratefully acknowledged.
References
1. K. Venkataraman, The Analytical Chemistry of Synthetic
Dyes, 1977, Wiley, New York, 372.
2. J. F. Dawson, J. S. D. C., 1983, 99, 183.
1356 ANALYTICAL SCIENCES NOVEMBER 2001, VOL. 17
Table 3 Selected bond lengths () and angles ()
Fig. 2 An ORTEP drawing of the title compound, representing
heavy atoms as 50% probability ellipsoids and H atoms as spheres of
arbitrary radius.