9-(2,6-Difluorophenoxycarbonyl)-10-methylacridinium trifluoromethane- sulfonate and its precursor 2,6-difluorophenyl acridine-9-carboxylate: C-H...O, C-F...π, S-O...π and π-π stacking interactions

Article abstract of DOI:10.1107/S0108270105033779

The title compounds, C₂₁H₁₄F₂NO ₂⁺·CF₃SO₃^-, (I), and C₂₀H₁₁F₂NO₂, (II), form monoclinic and triclinic crystals, respectivel

Full text of DOI:10.1107/S0108270105033779

organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
produce molecules of electronically excited 10-methyl-9-
acridinone (Rak et al., 1999), which emits light. The intensity
of the light is related directly to the concentration of the entity
assayed and this is the foundation for the analytical applica-
tion of chemiluminescence. Nevertheless, the use of acridin-
ium esters for labelling biomolecules entails certain
disadvantages. Although their chemiluminescence ef®ciency
in aqueous solutions is relatively high (up to 10%), they are
not very stable (Rak et al., 1999; Razawi & McCapra, 2000a,b);
they can react relatively fast with OH , which attacks the C
atom in position 9. Many attempts have been made to enhance
their resistance to hydrolysis, since this reaction competes with
the chemiluminescence pathway in alkaline media, yielding a
non-luminescent product, namely the non-excited 10-methyl-
9-acridinone (Hammond et al., 1991). Since the phenyl frag-
ment is removed during oxidation of phenyl 10-methyl-
acridinium-9-carboxylates, it is thought that the phenyl ring
substituents exert the greatest in¯uence on the ability to
chemiluminesce and on the properties of this group of
compounds (Sato, 1996; Rak et al., 1999). Wilson et al. (2001)
noted that reduction of 9-(2,6-di¯uorophenoxycarbonyl)-10-
methylacridinium (the title cation) yielded the corresponding
ester of acridan, which is not susceptible to nucleophilic
substitution (and thus hydrolysis). In this case, chemilumi-
nescence was triggered by the cathodic oxidation of the
acridan, which regenerates to the original acridinium salt
and decomposes to the electronically excited 10-methyl-9-
acridinone (a light emitter). It can thus be expected that
the presence of F atoms in the phenyl ring will improve the
resistance of such compounds to alkaline hydrolysis and
enhance their susceptibility to oxidation and their chemi-
luminescence ability. These were the premises for under-
taking investigations on the title chemiluminogens, namely
9-(2,6-di¯uorophenoxycarbonyl)-10-methylacridinium tri¯u-
oromethanesulfonate, (I), and 2,6-di¯uorophenyl acridine-9-
carboxylate, (II).
ISSN 0108-2701
9-(2,6-Difluorophenoxycarbonyl)-10-
methylacridinium trifluoromethane-
sulfonate and its precursor
2,6-difluorophenyl acridine-
9-carboxylate: CÐHÁ Á ÁO, CÐFÁ Á Áp,
SÐOÁ Á Áp and p±p stacking
interactions
Â
Artur Sikorski, Karol Krzyminski, Agnieszka Nizioøek and
.
Jerzy Bøazejowski*
Â
Â
University of Gdansk, Faculty of Chemistry, J. Sobieskiego 18, 80-952 Gdansk,
Poland
Correspondence e-mail: bla@chem.univ.gda.pl
Received 7 September 2005
Accepted 19 October 2005
Online 11 November 2005
+
The title compounds, C21H14F2NO2 ÁCF3SO3 , (I), and
C20H11F2NO2, (II), form monoclinic and triclinic crystals,
respectively. Adjacent cations of (I) are oriented in a `head-to-
tail' manner and are linked to one another via networks of CÐ
HÁ Á ÁO, CÐFÁ Á Áꢀ, SÐOÁ Á Áꢀ and multidirectional ꢀ±ꢀ inter-
actions. Adjacent molecules of (II) are also arranged in a
`head-to-tail' manner and are linked via networks of CÐ
HÁ Á ÁO and multidirectional ꢀ±ꢀ interactions. The mean planes
of the acridine moieties lie parallel in the lattices of both
compounds. The benzene rings are also parallel. However, the
acridine and di¯uorophenyl rings are mutually oriented at an
angle of 17.3 (2)ꢀ in (I) and 5.8 (2)ꢀ in (II). This mutual
orientation in various phenyl acridine-9-carboxylates and
related compounds is strongly in¯uenced by the nature of the
substituents on the phenyl fragment.
Comment
Most commercially available immunoassay tests utilizing
chemiluminescence employ derivatives of acridine-9-
carboxylic acid (Weeks et al., 1986; Rongen et al., 1994; Razawi
& McCapra, 2000a,b; Smith et al., 2000). Sensitivities at the
attomole level are available with this method, which makes
acridine-based labels more pro®table than standard radio-
In this paper, we present the results of our crystal structure
investigations, which were paralleled by laboratory studies on
the relationship between the structural and chemiluminogenic
properties of this group of compounds.
Parameters characterizing the geometry of the central ring
of the acridine moiety and the carboxyl fragment in (I) are
given in Table 1. The acridine moiety, with an average devia-
3
isotopic techniques (e.g. 125I or H) (Zomer & Jacquemijns,
2001). Among the most frequently used of these derivatives
are the phenyl esters of the 10-methylacridinium-9-carboxylic
acid cation (Dodeigne et al., 2000), although other compounds,
like hydroxamic or sulfohydroxamic esters, have been tested
in order to develop new assay options (Renotte et al., 2000).
These compounds react with H2O2 in alkaline media to
Ê
tion from planarity for its constituent atoms of 0.015 A, and
o690 # 2005 International Union of Crystallography
DOI: 10.1107/S0108270105033779
Acta Cryst. (2005). C61, o690±o694

organic compounds
the phenyl ring in (I) are mutually oriented at an angle of
17.3 (2)ꢀ (denoted by ꢁ, this is the angle between the mean
planes delineated by all the non-H atoms of the acridine and
phenyl moieties) (Fig. 1). The carboxyl group is twisted at an
angle of 67.6 (2)ꢀ relative to the acridine skeleton (denoted by
", this is the angle between the mean planes delineated by all
the non-H atoms of the acridine moiety and atoms C15, O16
and O17). The H atoms of the methyl group are disordered
over two orientations, twisted through 60ꢀ with respect to one
another, each with an occupancy of 0.5.
Arranged in a `head-to-tail' manner and related by a centre
of symmetry, two adjacent molecules of (II) are linked via two
CÐHÁ Á ÁO interactions [as in (I)] to produce dimers (Fig. 4
and Table 6). These are further linked by a network of
multidirectional ꢀ±ꢀ interactions involving the central acri-
dine ring, one of the lateral acridine rings and the phenyl ring
(Fig. 4 and Table 7), all of which makes for a stable molecular
crystal lattice.
In the crystalline phase, two adjacent cations of (I),
arranged in a `head-to-tail' manner and related by a centre of
symmetry, are linked via two CÐHÁ Á ÁO interactions to yield
dimers, which are, in turn, linked to anions via CÐHÁ Á ÁO
interactions to form strips (Fig. 2 and Table 2). These strips are
linked by networks of two types of CÐHÁ Á ÁO, CÐFÁ Á Áꢀ, SÐ
OÁ Á Áꢀ and ꢀ±ꢀ transverse interactions involving F atoms, O
atoms from the anion, and the acridine or phenyl rings (Fig. 2,
and Tables 3 and 4). This variety of interactions, rare in other
acridine derivatives, accounts for the stability of the crystalline
phase of (I).
Parameters characterizing the geometry of the central ring
of the acridine moiety and the carboxyl fragment in (II) are
given in Table 5. Angle ꢁ between the acridine (average
Ê
deviation from planarity for its constituent atoms = 0.003 A)
and phenyl moieties in (II) is 5.8 (2)ꢀ (Fig. 3). The carboxyl
group in (II) is twisted at an angle " = 78.8 (2)ꢀ relative to the
acridine skeleton. Comparison of the ꢁ and " angles for (I) and
(II) yields an inverse relationship.
Figure 2
The arrangement of the ions of (I) in the unit cell. The CÐHÁ Á ÁO
interactions are represented by dashed lines, and the YÐXÁ Á Áꢀ and ꢀ±ꢀ
interactions by dotted lines. H atoms not involved in CÐHÁ Á ÁO
interactions have been omitted. [Symmetry codes: (i) x 1, y, 1 + z;
(ii) 1 x, 1 y, 1 z; (iii) 1 x, y, 1 z; (iv) x, 12 y, z 21; (v) 1 + x,
1
2
1
2
y, z 12; (vi) x,
y, z 12.]
Figure 1
Figure 3
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.
The molecular structure of (II), showing the atom-labelling scheme and
25% probability displacement ellipsoids. H atoms are shown as small
spheres of arbitrary radii.
+
ꢁ
Acta Cryst. (2005). C61, o690±o694
Sikorski et al.
C21H14F2NO2 ÁCF3O3S and C20H11F2NO2 o691

organic compounds
Experimental
Compound (II) was prepared by heating anhydrous acridine-9-
carboxylic acid with a tenfold molar excess of thionyl chloride,
followed by esteri®cation of the resulting acid chloride with an
equimolar quantity of 2,6-di¯uorophenol (Sato, 1996). The reaction
was carried out in anhydrous dichloromethane in the presence of
triethylamine (1.5 molar excess) and a catalytic quantity of 4-(di-
methylamino)pyridine. The crude product was subsequently washed
with dilute HCl, NaHCO3 and saturated saline, and then puri®ed
chromatographically with silica gel as the stationary phase and
cyclohexane±ethyl acetate (1:1 v/v) as the mobile phase (yield 79%).
Analysis calculated for C22H14F5NO5S: C 71.6, H 3.3, N 4.2%; found:
C 71.5, H 3.3, N 25.1%. Yellow crystals of (II) suitable for X-ray
analysis were grown from cyclohexane (m.p. 454±455 K). Compound
(I) was synthesized by treating compound (II) dissolved in anhydrous
dichloromethane with a ®vefold molar excess of methyl tri¯uoro-
methanesulfonate dissolved in the same solvent (under an Ar
atmosphere at room temperature for 4 h). The crude salt was puri®ed
by repeated precipitation from an ethanol±diethyl ether (1:20 v/v)
solution (yield 86%). Pale-yellow crystals of (I) suitable for X-ray
investigations were grown from absolute ethanol (m.p. 504±506 K).
Figure 4
The arrangement of the molecules of (II) in the unit cell. The CÐHÁ Á ÁO
interactions are represented by dashed lines and the ꢀ±ꢀ interactions by
dotted lines. H atoms not involved in CÐHÁ Á ÁO interactions have been
x, 1 y,1 z; (ii) x, 1 y, z; (iii)
Compound (I)
Crystal data
omitted. [Symmetry codes: (i)
1
+
3
x, 1 y, 1 z.]
C21H14F2NO2 ÁCF3O3S
Dx = 1.576 Mg m
Mo Kꢃ radiation
Mr = 499.40
Monoclinic, P21=c
The geometry of the molecules in the crystalline phase is the
product of intramolecular forces and intermolecular inter-
actions. If some fragments are rigid, as with the acridine,
phenyl and carboxyl (O CÐOÐ) moieties in compounds (I)
and (II), the molecules can exist in a variety of structures as a
result of rotation around the single bonds, in the present case
C9ÐC15 and O16ÐC18. This provides the opportunity to
investigate the in¯uence of the structure of the molecular
fragments on their mutual arrangement and on the structure
of the whole molecules. Table 8 lists the angles ꢁ, re¯ecting the
mutual arrangement of the acridine and phenyl rings, and the
angles ", representing the relative arrangement of the acridine
ring and the carboxyl (or vinyl) group, for a series of phenyl
acridine-9-carboxylates, their relevant 10-methylacridinium
cations and related compounds. The angles ꢁ are the largest in
two known structures of styrylacridines. They are quite large if
bulky groups (Et) or atoms (Br, I) are ortho-substituted in the
phenyl ring of phenyl acridine-9-carboxylates. As far as the
halogen-disubstituted compounds are concerned, the angle ꢁ
in the ¯uoro derivatives of phenyl acridine-9-carboxylates and
their 10-methylacridinium cations is relatively small and
increases with the size of the halogen atom. All of the angles "
listed in Table 8 are larger than 50ꢀ and are not correlated with
either the angles ꢁ or the size and number of the substituents
in the phenyl fragment. The angles " are most probably the
outcome of the most ef®cient crystal packing. A property
which does not arise directly from the ꢁ values listed in Table
8, but which emerges from a meticulous analysis of crystal
phase structures, is that there is a relatively large number and
variety of intermolecular interactions in the di¯uoro deriva-
tives, which may be a consequence of the nearly parallel
mutual orientation of the acridine and phenyl rings.
Cell parameters from 50
re¯ections
Ê
Ê
a = 11.382 (2) A
b = 14.048 (3) A
ꢄ = 2.1±25.0ꢀ
ꢅ = 0.23 mm
T = 290 (2) K
1
Ê
c = 13.162 (3) A
ꢂ = 91.16 (3)ꢀ
V = 2104.1 (8) A
Z = 4
3
Ê
Prism, yellow
0.5 Â 0.3 Â 0.2 mm
Data collection
Kuma KM-4 diffractometer
ꢄ/2ꢄ scans
3874 measured re¯ections
3700 independent re¯ections
1760 re¯ections with I > 2ꢆ(I)
Rint = 0.029
h = 13 ! 13
k = 0 ! 16
l = 0 ! 15
3 standard re¯ections
every 200 re¯ections
intensity decay: 4.5%
ꢄ
max = 25.0ꢀ
Re®nement
Re®nement on F2
R[F2 > 2ꢆ(F2)] = 0.048
wR(F2) = 0.144
S = 0.97
3700 re¯ections
w = 1/[ꢆ2(Fo2) + (0.0693P)2
+ 0.9523P]
where P = (Fo + 2Fc2)/3
2
(Á/ꢆ)max < 0.001
3
Ê
Áꢇmax = 0.27 e A
3
Ê
0.32 e A
309 parameters
H-atom parameters constrained
Áꢇmin
=
Extinction correction: SHELXL97
(Sheldrick, 1997)
Extinction coef®cient: 0.0096 (9)
Table 1
Selected geometric parameters (A, ) for (I).
ꢀ
Ê
N10ÐC12
N10ÐC14
C15ÐO16
C15ÐO17
1.367 (5)
1.363 (5)
1.355 (4)
1.179 (4)
O16ÐC18
C19ÐF24
C23ÐF25
1.401 (4)
1.336 (5)
1.352 (4)
C9ÐC15ÐO16
111.9 (3)
64.2 (5)
C9ÐC15ÐO17
124.6 (3)
96.3 (4)
C11ÐC9ÐC15ÐO17
C15ÐO16ÐC18ÐC19
+
ꢁ
o692 Sikorski et al. C21H14F2NO2 ÁCF3O3S and C20H11F2NO2
Acta Cryst. (2005). C61, o690±o694

organic compounds
Table 2
Hydrogen-bond geometry (A, ) for (I).
Table 5
Selected geometric parameters (A, ) for (II).
ꢀ
ꢀ
Ê
Ê
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
N10ÐC12
N10ÐC14
C15ÐO16
C15ÐO17
1.339 (3)
1.337 (3)
1.352 (3)
1.180 (3)
O16ÐC18
C19ÐF24
C23ÐF25
1.395 (2)
1.342 (3)
1.347 (3)
C4ÐH4Á Á ÁO29i
C5ÐH5Á Á ÁO28ii
C22ÐH22Á Á ÁO17iii
0.93
0.93
0.93
2.54
2.59
2.52
3.225 (5)
3.417 (5)
3.316 (5)
131
148
144
Symmetry codes: (i) x 1; y; z ‡ 1; (ii) 1 x; 1 y; 1 z; (iii) 1 x; y; 1 z.
C9ÐC15ÐO16
110.6 (2)
78.1 (3)
C9ÐC15ÐO17
125.9 (2)
104.9 (3)
C11ÐC9ÐC15ÐO17
C15ÐO16ÐC18ÐC19
Table 3
ꢀ
Ê
YÐXÁ Á Áꢀ interactions in (I) (A, ).
Cg1 is the centroid of ring C9/C11/C12/N10/C14/C13, Cg2 of ring C1±C4/C12/
C11, Cg3 of ring C5±C8/C13/C14 and Cg4 of ring C18±C23.
Table 6
Hydrogen-bond geometry (A, ) for (II).
ꢀ
Ê
YÐX
Cg
XÁ Á ÁCg
YÁ Á ÁCg
YÐXÁ Á ÁCg
DÐHÁ Á ÁA
C22ÐH22Á Á ÁO17i
Symmetry codes: (i)
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
C19ÐF24
C23ÐF25
S27ÐO28
S27ÐO28
S27ÐO29
S27ÐO29
2iv
4iii
1v
2v
1v
3v
3.874 (3)
3.977 (3)
3.511 (3)
3.374 (3)
3.569 (4)
3.835 (4)
4.109 (4)
4.383 (4)
3.708 (2)
4.080 (2)
3.708 (2)
4.740 (2)
90.5 (2)
98.4 (2)
86.74 (13)
110.17 (14)
84.22 (14)
121.64 (16)
0.93
2.55
3.395 (4)
151
x
1; 1 y; 1 z.
1
.
Symmetry codes: (iii) 1 x; y; 1 z; (iv) x; 12 y; z 21; (v) 1 ‡ x; 21 y; z
Table 7
ꢀ±ꢀ interactions in (II) (A, ).
2
ꢀ
Ê
Table 4
ꢀ±ꢀ interactions in (I) (A, ).
The centroids are as in Table 3. The dihedral angle is between the CgI and CgJ
planes and the interplanar distance is the perpendicular distance of CgI from
ring J and the offset is the perpendicular distance of ring I from ring J.
ꢀ
Ê
The centroids are as in Table 3. The dihedral angle is between the CgI and CgJ
planes and the interplanar distance is the perpendicular distance of CgI from
ring J and the offset is the perpendicular distance of ring I from ring J.
CgI
CgJ
CgÁ Á ÁCg
Dihedral angle
Interplanar distance
Offset
1
1
2
2
2
4
4
2ii
3.912 (2)
3.735 (2)
3.912 (2)
3.514 (2)
3.787 (2)
3.735 (2)
3.787 (2)
1.1
6.3
1.1
0.0
6.3
6.3
6.3
3.459 (3)
3.469 (3)
3.427 (3)
3.444 (3)
3.406 (3)
3.535 (3)
3.527 (3)
1.472 (2)
1.413 (2)
1.740 (2)
1.634 (2)
1.472 (2)
1.413 (2)
1.740 (2)
4iii
1ii
CgI
CgJ
CgÁ Á ÁCg
Dihedral angle
Interplanar distance
Offset
1
3
4
4
4vi
4vi
1iv
3iv
3.620 (2)
3.940 (3)
3.620 (2)
3.940 (3)
7.8
6.4
7.8
6.4
3.424 (2)
3.482 (3)
3.530 (2)
3.527 (3)
1.841 (2)
1.003 (3)
1.037 (2)
1.570 (3)
2ii
4iii
1iii
2iii
Symmetry codes: (iv) x; 12 y; z 21; (vi) x; 21 y; 12 ‡ z.
Symmetry codes: (ii) x; 1 y; z; (iii) x; 1 y; 1 z.
Compound (II)
Table 8
The angles between the acridine and phenyl rings (ꢁ, ꢀ), and between the
acridine ring and the carboxyl or vinyl fragment (", ꢀ), in substituted
phenyl acridine-9-carboxylates, their relevant 10-methylacridinium
cations and related compounds.
Crystal data
C20H11F2NO2
Mr = 335.30
Triclinic, P1
a = 8.306 (2) A
Ê
b = 9.057 (2) A
c = 11.423 (2) A
ꢃ = 69.94 (3)ꢀ
ꢂ = 77.80 (3)ꢀ
ꢈ = 72.16 (3)ꢀ
Z = 2
Dx = 1.460 Mg m
Mo Kꢃ radiation
3
Ê
Cell parameters from 50
re¯ections
Compound
ꢁ
"
Reference
ꢄ = 2.5±25.0ꢀ
ꢅ = 0.11 mm
T = 290 (2) K
Ê
1
(I)
(II)
(III)
(IV)
(V)
(VI)
(VII)
(VIII)
(IX)
(X)
(XI)
(XII)
(XIII)
(XIV)
17.3 (2)
5.8 (2)
67.6 (2)
78.8 (2)
56.5 (2)
57.9 (2)
67.3 (2)
68.1 (2)
77.2 (2)
51.0 (2)
54.3 (2)
89.0 (2)
62.0 (2)
60.6 (3)
55.5 (2)
69.9 (3)
This work
This work
Meszko et al. (2002)
To be published
Sikorski et al. (2005a)
Sikorski et al. (2005a)
Sikorski et al. (2005b)
Sikorski et al. (2005d)
To be published
35.9 (2)
30.2 (2)
62.1 (2)
35.7 (2)
9.3 (2)
41.2 (2)
45.5 (2)
27.2 (2)
33.4 (2)
35.9 (3)
67.1 (2)
73.7 (3)
Prism, yellow
0.4 Â 0.3 Â 0.2 mm
3
Ê
V = 762.9 (3) A
Data collection
Kuma KM-4 diffractometer
ꢄ/2ꢄ scans
2875 measured re¯ections
2681 independent re¯ections
1314 re¯ections with I > 2ꢆ(I)
Rint = 0.023; ꢄmax = 25.0ꢀ
h = 9 ! 9
k = 10 ! 10
To be published
l = 0 ! 13
Sikorski et al. (2005b)
Sikorski et al. (2005c)
Sgarabotto et al. (1989)
Sgarabotto et al. (1989)
3 standard re¯ections
every 200 re¯ections
intensity decay: 1.0%
Re®nement
Compounds: (I) 9-(2,6-di¯uorophenoxycarbonyl)-10-methylacridinium tri¯uoro-
methanesulfonate; (II) 2,5-di¯uorophenyl acridine-9-carboxylate; (III) 2-methylphenyl
2-methoxyacridine-9-carboxylate; (IV) 2-methylphenyl acridine-9-carboxylate; (V)
2-ethylphenylacridine-9-carboxylate; (VI) 2,5-dimethylphenyl acridine-9-carboxylate;
(VII) 2,5-dichlorophenyl acridine-9-carboxylate; (VIII) 2,5-dibromophenyl acridine-9-
carboxylate; (IX) 2,5-diiodophenyl acridine-9-carboxylate; (X) 9-(2-methylphenoxy-
carbonyl)-10-methylacridinium tri¯uoromethanesulfonate; (XI) 9-(2,6-dichlorophenoxy-
carbonyl)-10-methylacridinium tri¯uoromethanesulfonate; (XII) 9-(2,6-dibromo-
phenoxycarbonyl)-10-methylacridinium tri¯uoromethanesulfonate; (XIII) (E)-9-styryl-
acridine; (XIV) (Z)-9-(2,5-dimethylstyryl)acridine.
Re®nement on F2
R[F2 > 2ꢆ(F2)] = 0.042
wR(F2) = 0.129
S = 1.01
2681 re¯ections
w = 1/[ꢆ2(Fo2) + (0.0607P)2
+ 0.1152P]
where P = (Fo2 + 2Fc2)/3
(Á/ꢆ)max < 0.001
3
Ê
Áꢇmax = 0.18 e A
Áꢇmin
3
Ê
0.16 e A
227 parameters
H-atom parameters constrained
=
Extinction correction: SHELXL97
Extinction coef®cient: 0.0025 (4)
+
ꢁ
Acta Cryst. (2005). C61, o690±o694
Sikorski et al.
C21H14F2NO2 ÁCF3O3S and C20H11F2NO2 o693

organic compounds
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National
Laboratory, Tennessee, USA.
Kuma (1989). KM-4 Software User's Guide. Version 3.1. Kuma Diffraction,
Wrocøaw, Poland.
Â
Ç
Meszko, J., Krzyminski, K., Konitz, A. & Bøazejowski, J. (2002). Acta Cryst.
The methyl H atoms in (I) were located in difference Fourier
Ê
syntheses and re®ned as a rigid rotating group, with CÐH = 0.96 A
and Uiso(H) = 1.5Ueq(C). These H atoms were assumed to have two
unique disordered orientations with an occupancy factor of 0.5. All
other H atoms in (I) and (II) were placed geometrically and re®ned
Ê
using a riding model, with CÐH distances of 0.93 A and with
Uiso(H) = 1.2Ueq(C).
C58, o157±o158.
Rak, J., Skurski, P. & Bøazejowski, J. (1999). J. Org. Chem. 64, 3002±3008.
Ç
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