Ζ. Kristallogr. N C S 2 1 6 (2001) 2 9 9 - 3 0 0 2 9 9
© by Oldenbourg Wissenschaftsverlag, München
Crystal structure of l,4-bis(ethylamino)anthracene-9,10-dione,
C I
8H
1 8N
20
2G . M . S c h n e i d e r *1, D . T u m a1, M . W i n t e r " a n d B . W a g n e r1"
' Ruhr-Universität Bochum, Fakultät für Chemie, Physikalische Chemie, D^t4780 Bochum, Germany
" Ruhr-Universität Bochum, Fakultät für Chemie, Lehrstuhl für Anorganische Chemie II, D-44780 Bochum, Germany
111 Accumulatorenwerke Hoppecke Carl Zoellner & Sohn GmbH & Co KG, Abteilung GTB, Bontkirchener Straße 2, D-59929 Brilon, Germany Received December 5, 2000, CCDC-No. 1267/575
Table 1. Data collection and handling.
Abstract
C |8Hi8N20 2 , m o n o c l i n i c , C 1 2 / c l ( N o . 15), A = 1 4 . 1 6 1 ( 2 ) Ä , b= 1 5 . 5 6 7 ( 1 ) Ä , c = 6 . 9 8 8 3 ( 8 ) Ä , ß = 106.50(1)°, V= 1477.2 Ä3, Ζ = 4, Rgl(F) = 0 . 0 3 8 , wRretfF2) = 0 . 0 9 2 , T= 2 9 3 K .
Crystal: dark blue needle.
size 0.46 χ 0.48 χ 0.58 mm
Wavelength: Mo Ka radiation (0.71073 A)
μ: 0.87 cm"1
Diffractometer, scan mode: Siemens P4, ω
2 θ max • 50°
WAWJmeasunxl, N(hkliumquc'· 1347, 1295 Criterion for /obs, N(hkl)g. / o b s > 2 o ( W , 8 9 5 N(param)refined: 107
Program: SHELXL-97 [5]
Table 2. Atomic coordinates and displacement parameters (in A2).
Atom Site X y ζ t/iso
H(l) 8/ -0.2274 0.5022 0.0051 0.069
H(2) 8 / -0.0813 0.6761 0.1685 0.066
H(7) 8 / -0.0817 0.1006 0.1607 0.083
H(8) 8 / -0.1646 0.2276 0.0723 0.066
H(15A) 8 / -0.2258 0.6650 -0.0860 0.075
H(15B) 8 / -0.2562 0.6578 0.1127 0.075
H(16A) 8 / -0.3975 0.6580 -0.1632 0.126
H(16B) 8 / -0.3902 0.5704 -0.0491 0.126
H(16C) 8 / -0.3593 0.5757 -0.2471 0.126
Source of material
l , 4 - B i s ( e t h y l a m i n o ) a n t h r a c e n e - 9 , 1 0 - d i o n e ( C . I. S o l v e n t B l u e 5 9 ) w a s p u r c h a s e d f r o m A l d r i c h . S i n g l e c r y s t a l s w e r e o b t a i n e d f r o m a filtered m e t h a n o l i c s o l u t i o n b y s l o w l o w e r i n g o f t h e t e m - p e r a t u r e f r o m 3 3 0 Κ t o r o o m t e m p e r a t u r e in a w a t e r b a t h [1],
Discussion
l , 4 - B i s ( e t h y l a m i n o ) a n t h r a c e n e - 9 , 1 0 - d i o n e w a s p a r t of c o m p r e - h e n s i v e s t u d i e s o n the solubility o f a n t h r a q u i n o n e d i s p e r s e d y e s in near- a n d supercritical f l u i d s [2], It e x h i b i t s i n t r a m o l e c u l a r Ν1 — Η 1 - 0 1 h y d r o g e n b o n d s [ 2 . 5 8 6 ( 3 ) Ä ] s i m i l a r t o t h o s e in t h e isopropyl [3] a n d p h e n y l [4] d e r i v a t i v e s .
* Correspondence author
(e-mail: gerhard.schneider@nihr-uni-bochum.de)
300
1,4-Bis(ethylamino)anthracene-9,10-dioneTable 3. Atomic coordinates and displacement parameters (in A2).
A t o m S i t e X ζ l / i i Un 1/33 Un Un t / 2 3
0(1) 8 / -0.1930(1) 0.3841(1) 0.0422(3) 0.041(1) 0.056(1) 0.073(2) 0.003(1) -0.001(1) 0.001(1) N(l) 8 / -0.1977(2) 0.5501(1) 0.0429(4) 0.056(2) 0.047(2) 0.064(2) 0.009(2) 0.007(2) -0.005(1) C(l) 8 / -0.1014(2) 0.5461(2) 0.1446(4) 0.051(2) 0.046(2) 0.046(2) -0.002(2) 0.015(2) -0.002(2) C(2) 8 / -0.0484(2) 0.6240(2) 0.2006(4) 0.064(2) 0.042(2) 0.063(3) 0.003(2) 0.023(2) 0.006(2) C(7) 8 / -0.0488(2) 0.1524(2) 0.1968(4) 0.077(3) 0.045(2) 0.077(3) -0.004(2) 0.009(2) 0.002(2) C(8) 8 / -0.0982(2) 0.2282(2) 0.1436(4) 0.052(2) 0.045(2) 0.062(2) -0.004(2) 0.005(2) -0.001(2) C(9) 8 / -0.1031(2) 0.3875(2) 0.1382(4) 0.045(2) 0.043(2) 0.044(2) 0.003(2) 0.010(2) 0.001(2) C ( l l ) 8 / -0.0511(2) 0.4675(2) 0.1960(4) 0.045(2) 0.040(2) 0.041(2) 0.001(2) 0.009(2) -0.000(2) C(14) 8 / -0.0496(2) 0.3065(2) 0.1960(4) 0.040(2) 0.042(2) 0.044(2) -0.000(2) 0.010(2) 0.003(2) C(15) 8 / -0.2554(2) 0.6276(2) -0.0082(5) 0.061(2) 0.054(2) 0.072(2) 0.024(2) 0.017(2) 0.011(2) C(16) 8 / -0.3603(2) 0.6059(2) -0.1280(4) 0.064(2) 0.080(2) 0.093(3) 0.028(2) -0.001(2) 0.007(2)
Acknowledgments. We thank the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie for generous financial support.
References
1. Wagner, B.: Untersuchungen zur Löslichkeit von Anthrachinonfarb- stoffen in nah- und überkritischem Kohlendioxid mit einer Strömungs- methode bis 20 MPa. Dissertation, Ruhr-Universität Bochum 1998.
2. Tuma, D.; Wagner, B.; Schneider, G. M.: Comparative Solubility Investi- gations of Anthraquinone Disperse Dyes in Near- and Supercritical Fluids, Fluid Phase Equilibria, in press.
3. Brown, C. J.; Mitchell, G. R.: 1,4-Bis(isopropylamino)anthraquinone, ActaCrystallogr. B38(1982) 3149-3151.
4. Yatsenko, Α. V.; Tafeenko, V. Α.; Zhukov, S. G.; Medvedev, S. V.;
Popov, S. I.: Crystal structure of l,4-bis-(phenylamino)-anthracene- 9,10-dione, Z. Kristallogr. NCS 210 (1995) 969-970.
5. Sheldrick, G. M.: SHELXL-97, Program for the Refinement of Crystal Structures. University of Göttingen, Germany 1997.
