1
68
Eagle, Kavallieratos, and Bryan
t-butyl group is disordered and is modeled over
two sites (52:48 for C18–C20). No restraints
were applied to the refinement of the disordered
atoms. The highest peak in the final difference
�
3
˚
map measured 0.54 e � A .
0
N,N -Bis(4-t-butylphenyl)-1,3-benzenedisul-
fonamide � 1,2-dichloroethane, (2 � ClCH CH
2
2
Cl). Suitable crystals were obtained from 1,2-
dichloroethane. Cell constants and an orientation
matrix were obtained from a crystal measuring
3
0
.44 � 0.24 � 0.11 mm , by least squares refine-
ment, using the setting angles of 25 reflections in
0
Fig. 1. Molecular structure of N,N -diphenyl-1,3-benzene-
�
the range 10 < � < 19 . Both t-butyl groups are
disulfonamide, (1), showing 50% probability displacement
ellipsoids. Most H atoms are omitted for clarity.
disordered, and are modeled as a twofold disorder
(68:32 for C17–C20 and 60:40 for C27–C30).
All chemically equivalent bond distances and
angles between and within the two disordered
groups are restrained to be roughly equal. Within
each disordered group, the Ui j components
benzenedisulfonamide structures (2 � CF CH OH
3
2
and 2 � ClCH CH Cl) adopt the same overall con-
2
2
formation, while 1 adopts a different conforma-
tion. The primary difference is in the C C S N
(rotation about the C S bond) torsion angles,
of bonded atoms or disordered atoms within
˚
�
0
.7 A of each other are restrained to be similar.
which are 124.0(1) and 127.8(1) in 1, and range
�
Despite these restraints the thermal ellipsoids
of some disordered atoms exhibit unusual elon-
gation, suggesting further, unresolved disorder.
The positional parameters for amide H atoms
were allowed to refine, although the two N H
distances were restrained to be approximately
equal. The highest peak in the final difference
from 40.4(5) to 54.8(5) in the structures of 2. Ba-
sically this places the central arene group between
the N H groups in 1, while these groups appear
to have mostly empty space between them in 2.
These relative orientations of the N H groups
have been termed “anti–anti” and “syn–syn,”
respectively.4 The syn–syn conformation, as
�
3
˚
map measured 0.90 e � A , and the lowest
�
3
˚
valley � 0.70 e � A .
Results and Discussion
The structures of 1, 2 � CF CH OH and
3
2
2
� ClCH CH Cl are illustrated in Figs. 1–3, re-
2
2
spectively. The configuration of each disulfon-
amide molecule can be expressed in terms of the
six torsion angles for the six single bonds that lie
between the three arene rings (Table 2). In terms
of orienting the N H groups for anion binding,
only rotation about the C S and S N bonds are
important, as rotation about the N C bonds only
determines the relative position of the outer arene
rings (C11–C16 and C21–C26). As can be seen in
0
Fig. 2. Molecular structure of N,N -bis(4-t-butylphenyl)-
1
,3-benzenedisulfonamide � 1,1,1-trifluoroethanol, (2 � CF
3
CH OH), showing 50% probability displacement ellipsoids.
2
Minor disorder components and most H atoms are omitted
for clarity.
0
Table 2, the two N,N -bis(4-t-butylphenyl)-1,3-
Eagle, Cassandra T.
