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organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
quantum yields of light emission and stability (Adamczyk et
al., 1999; Dodeigne et al., 2000; Razawi & McCapra, 2000;
Renotte et al., 2000; Smith et al., 2000; Zomer & Jacquemijns,
2001). Continuing the search for new analytically interesting
acridine-based chemiluminogens, we synthesized phenyl acri-
dine-9-carboxylate substituted with two Cl atoms, (II), and its
tri¯uoromethanesulfonate salt, (I), methylated at the endo-
cyclic N atom, in order to determine how the presence of
heavy Cl atoms in the phenyl fragment affects the stability
and chemiluminogenic ability of this group of compounds.
Presenting as it does the crystal structure of chemiluminogen
(I) and its precursor (II), this paper extends, together with our
earlier publications on the crystallography of phenyl acridine-
9-carboxylates (Meszko et al., 2002; Sikorski et al., 2005), the
range of chemiluminogens with potentially interesting appli-
cations.
ISSN 0108-2701
9-(2,6-Dichlorophenoxycarbonyl)-
10-methylacridinium trifluoro-
methanesulfonate and its precursor
2,6-dichlorophenyl acridine-
9-carboxylate
a
a
b,a
Â
Artur Sikorski, Karol Krzyminski, Antoni Konitz and
.
Jerzy Bøazejowskia*
a
Â
Â
University of Gdansk, Faculty of Chemistry, J. Sobieskiego 18, 80-952 Gdansk,
Poland, and bGdansk University of Technology, Department of Inorganic Chemistry,
Â
Â
G. Narutowicza 11/12, 80-952 Gdansk, Poland
Correspondence e-mail: bla@chem.univ.gda.pl
Received 22 December 2004
Accepted 8 February 2005
Online 11 March 2005
+
The title compounds, C21H14Cl2NO2 ÁCF3O3S , (I), and
C20H11Cl2NO2, (II), form triclinic crystals. Adjacent cations
of (I) are oriented either parallel or antiparallel; in the latter
case, they are related by a centre of symmetry. Together with
the CF3SO3 anions, the antiparallel-oriented cations of (I)
form layers in which the molecules are linked via a network of
CÐHÁ Á ÁO and ꢀ±ꢀ interactions (between the benzene rings).
These layers, in turn, are linked via a network of multi-
directional ꢀ±ꢀ interactions between the acridine rings, and
the whole lattice is stabilized by electrostatic interactions
between ions. Adjacent molecules of (II) are oriented either
parallel or antiparallel; in the latter case, they are related by a
centre of symmetry. Parallel-oriented molecules are arranged
in chains stabilized via CÐHÁ Á ÁCl interactions. These chains
are oriented either parallel or antiparallel and are stabilized,
in the latter case, via multidirectional ꢀ±ꢀ interactions and
more generally via dispersive interactions. Acridine and
independent benzene moieties lie parallel in the lattices of
(I) and (II), and are mutually oriented at an angle of 33.4 (2)ꢀ
in (I) and 9.3 (2)ꢀ in (II).
With respective average deviations from planarity of 0.0077
Ê
and 0.0094 A, the acridine and benzene moieties in (I) are
oriented at an angle of 33.4 (2)ꢀ (de®ned as ꢁ, the angle
between the mean planes delineated by all the non-H atoms of
the acridine and benzene moieties; Fig. 1 and Table 1). The
carboxyl group is twisted at an angle of 62.0 (2)ꢀ relative to the
acridine skeleton (de®ned as ", the angle between the mean
Comment
Numerous acridine-based derivatives are important owing to
their chemiluminogenic ability and their utility as chemilu-
minescent indicators or fragments of chemiluminescent labels,
with applications in immunoassays, nucleic acid diagnostics
and quantitative assays of biomolecules, such as antigens,
antibodies, hormones and enzymes, as well as DNA±RNA
structural analyses (Becker et al., 1999; Dodeigne et al., 2000;
Zomer & Jacquemijns, 2001). Among acridine-based chemi-
luminogens, phenyl acridine-9-carboxylates are the most
promising analytical agents, since they exhibit relatively high
Figure 1
The molecular structure of (I), showing the atom-labelling scheme and
25% probability displacement ellipsoids. H atoms are shown as small
spheres of arbitrary radii.
Acta Cryst. (2005). C61, o227±o230
DOI: 10.1107/S0108270105004506
# 2005 International Union of Crystallography o227
Sikorski, Artur
