π-Stacked hydrogen-bonded dimers in 2-(2-nitrophenylaminocarbonyl)-benzoic acid, and hydrogen-bonded sheets in orthorhombic and monoclinic polymorphs of 2-(4-nitrophenylaminocarbonyl)benzoic acid

Article abstract of DOI:10.1107/S0108270103027914

Molecules of 2-(2-nitrophenylaminocarbonyl)benzoic acid, C ₁₄H₁₀N₂O₅, are linked into centrosymmetric R₂²(8) dimers by a single O-H...O hydrogen bond [H...O = 1.78 A, O...O = 2.623 (2) A and O-H...O = 178°] and these dimers are linked into sheets by a single aromatic π-π stacking interaction. The isomeric compound 2-(4-nitrophenylamino-carbonyl)benzoic acid crystallizes in two polymorphic forms. In the orthorhombic form (space group P2₁2₁2 ₁ with Z′ = 1, crystallized from ethanol), the molecules are linked into sheets of R₄⁴(22) rings by a combination of one N-H...O hydrogen bond [H...O = 1.96 A, N...O = 2.833 (3) A and N-H...O = 171°] and one O-H...O hydrogen bond [H...O = 1.78 A, O...O = 2.614 (3) A and O-H...O = 173°]. In the monoclinic form (space group P2₁/n with Z′ = 2, crystallized from acetone), the molecules are linked by a combination of two N-H...O hydrogen bonds [H...O = 2.09 and 2.16 A, N...O = 2.873 (4) and 2.902 (3) A, and N-H...O = 147 and 141°] and two O-H...O hydrogen bonds [H...O = 1.84 and 1.83 A, O...O = 2.664 (3) and 2.666 (3) A, and O-H...O = 166 and 174°] into sheets of some complexity. These sheets are linked into a three-dimensional framework by a single C-H...O hydrogen bond [H...O = 2.45 A, C...O = 3.355 (4) A and C-H...O = 160°].

Full text of DOI:10.1107/S0108270103027914

organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
ammonium hydrogenphthalates, (C). We have recently
reported the supramolecular structure of a type (C) salt,
4-iodoanilinium 3-nitrophthalate(1� ) (Glidewell et al., 2003),
and we report here the molecular and supramolecular struc-
ISSN 0108-2701
tures of two examples of the type (A) intermediate, namely
2-(2-nitrophenylaminocarbonyl)benzoic acid, (I) (Fig. 1), and
two polymorphs of 2-(4-nitrophenylaminocarbonyl)benzoic
acid, viz. orthorhombic, (II) (Fig. 2), and monoclinic, (III)
(Fig. 3).
p-Stacked hydrogen-bonded dimers
in 2-(2-nitrophenylaminocarbonyl)-
benzoic acid, and hydrogen-bonded
sheets in orthorhombic and mono-
clinic polymorphs of 2-(4-nitro-
phenylaminocarbonyl)benzoic acid
a
b
Christopher Glidewell, * John N. Low, Janet M. S.
b
c
Skakle and James L. Wardell
a
School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland,
b
Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen
c
AB24 3UE, Scotland, and Departamento de Qu Âõ mica Inorg aà nica, Instituto de
Qu Âõ mica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ,
Brazil
Correspondence e-mail: cg@st-andrews.ac.uk
Received 25 November 2003
Accepted 3 December 2003
Online 10 January 2004
Molecules of 2-(2-nitrophenylaminocarbonyl)benzoic acid,
2
C H N O , are linked into centrosymmetric R (8) dimers
1
4
10
2
5
2
Ê
by a single OÐHÁ Á ÁO hydrogen bond [HÁ Á ÁO = 1.78 A,
Ê
ꢀ
OÁ Á ÁO = 2.623 (2) A and OÐHÁ Á ÁO = 178 ] and these dimers
are linked into sheets by a single aromatic ꢀ±ꢀ stacking
interaction. The isomeric compound 2-(4-nitrophenylamino-
carbonyl)benzoic acid crystallizes in two polymorphic forms.
In each of compounds (I)±(III), the central C11Ð
C17(O17)ÐN1ÐC21 fragment of the molecule is essentially
planar, with a trans amide conformation. The C11±C16 and
C21±C26 rings are considerably rotated away from this plane,
as indicated by the key torsion angles (Tables 1, 3 and 5). In
(I), the carboxyl and nitro groups make dihedral angles of
0
In the orthorhombic form (space group P2 2 2 with Z = 1,
1
1 1
crystallized from ethanol), the molecules are linked into sheets
4
of R (22) rings by a combination of one NÐHÁ Á ÁO hydrogen
4
Ê
Ê
bond [HÁ Á ÁO = 1.96 A, NÁ Á ÁO = 2.833 (3) A and NÐHÁ Á ÁO =
ꢀ
ꢀ
Ê
29.9 (2) and 36.5 (2) , respectively, with the adjacent aryl rings,
ꢀ
1
71 ] and one OÐHÁ Á ÁO hydrogen bond [HÁ Á ÁO = 1.78 A,
Ê
ꢀ
and in (II), the corresponding angles are 12.2 (2) and 11.1 (2) ,
respectively. In (III), these dihedral angles are 7.7 (2) and
OÁ Á ÁO = 2.614 (3) A and OÐHÁ Á ÁO = 173 ]. In the monoclinic
0
form (space group P2 /n with Z = 2, crystallized from
1
ꢀ
ꢀ
1
3.0 (2) , respectively, in molecule A, and 10.1 (2) and 6.5 (1)
acetone), the molecules are linked by a combination of two
Ê
in molecule B. The CÐO distances in the carboxyl groups are
consistent with the location of the fully ordered carboxyl H
atoms, as identi®ed from difference maps. The other bond
distances and angles show no exceptional features.
NÐHÁ Á ÁO hydrogen bonds [HÁ Á ÁO = 2.09 and 2.16 A, NÁ Á ÁO
Ê
ꢀ
=
2.873 (4) and 2.902 (3) A, and NÐHÁ Á ÁO = 147 and 141 ]
Ê
and two OÐHÁ Á ÁO hydrogen bonds [HÁ Á ÁO = 1.84 and 1.83 A,
Ê
OÁ Á ÁO = 2.664 (3) and 2.666 (3) A, and OÐHÁ Á ÁO = 166 and
ꢀ
In compound (I) (Fig. 1), there is an intramolecular NÐ
HÁ Á ÁO hydrogen bond forming an S(6) motif (Bernstein et al.,
1995). The supramolecular aggregation is dominated by a
single OÐHÁ Á ÁO hydrogen bond, propagated by aromatic ꢀ±
1
74 ] into sheets of some complexity. These sheets are linked
into a three-dimensional framework by a single CÐHÁ Á ÁO
Ê
Ê
hydrogen bond [HÁ Á ÁO = 2.45 A, CÁ Á ÁO = 3.355 (4) A and
ꢀ
CÐHÁ Á ÁO = 160 ].
ꢀ
stacking interactions. Carboxyl atom O11 in the molecule at
(
x, y, z) acts as hydrogen-bond donor to carboxyl atom O12 in
Comment
the molecule at (1 � x, 1 � y, 1 � z), so generating a centro-
2
The reaction of C-substituted anilines with phthalic anhydride
initially yields N-arylaminocarbonylbenzoic acids, (A) (see
scheme). Dehydration of this type of intermediate yields
N-arylphthalimides, (B), while hydrolysis yields aryl-
symmetric dimer characterized by the usual R (8) motif and
1
2
1 1
2 2
centred at ( , , ) (Fig. 4).
2
The ꢀ±ꢀ stacking interaction involves the nitro-substituted
ring of the molecule at (x, y, z), which is part of the dimer
o120 # 2004 International Union of Crystallography
DOI: 10.1107/S0108270103027914
Acta Cryst. (2004). C60, o120±o124

organic compounds
1
2
1 1
2 2
centred at ( , , ), and the corresponding rings of the mol-
3
motifs so characteristic of simple carboxylic acids, namely the
2
1
3
1
ecules at ( + x, y, � z) and (x � , y, � z), which them-
R (8) dimer [cf. compound (I)] and the C(4) chain. Likewise,
2
2
2
2
2
1
selves are components of the dimers centred at (1, , 1) and
1
the amide group in (II) does not form the C(4) chain often
found in simple carboxylic amides, but instead each of the two
hydrogen bonds in (II) utilizes a donor and an acceptor from
2
(
rings of this type is ca 9.5 , with a centroid separation of
0, , 1), respectively. The interplanar angle between adjacent
ꢀ
Ê Ê
2
3
gation by inversion of this interaction also links the ( , , )
.793 (2) A and an interplanar spacing of ca 3.42 A. Propa-
1
1 1
2 2
2
1
1
dimer to those centred at (0, , 0) and (1, , 0), and hence the
2
2
2
R (8) dimers are linked into an (010) sheet (Fig. 5).
2
Whereas the supramolecular structure of (I) is controlled by
a combination of OÐHÁ Á ÁO hydrogen bonds and aromatic ꢀ±
ꢀ
stacking interactions, with the NÐH bond participating only
in an intramolecular hydrogen bond, the supramolecular
aggregation in polymorphic compounds (II) and (III) is
controlled by a combination of NÐHÁ Á ÁO and OÐHÁ Á ÁO
hydrogen bonds. While ꢀ±ꢀ stacking interactions and XÐ
HÁ Á Áꢀ(arene) hydrogen bonds (X is C, N or O) are all absent
from the structures of (II) and (III), there are two CÐHÁ Á ÁO
hydrogen bonds present in (III).
In compound (II), the amidic atom N1 in the molecule at (x,
y, z) acts as hydrogen-bond donor to carboxyl atom O12 in the
molecule at (x � 1, y, z), so generating by translation a C(7)
chain running parallel to the [100] direction. At the same time,
carboxyl atom O11 at (x, y, z) acts as hydrogen-bond donor to
Figure 3
The two independent molecules in compound (III), showing the atom-
labelling scheme. Displacement ellipsoids are drawn at the 30%
probability level.
1
1
amidic atom O17 in the molecule at (1 � x, + y, 2 � z), so
2
producing a spiral C(7) chain running parallel to the [010]
1
1
direction and generated by the 2 screw axis along ( , y, ). It is
1
2
4
noteworthy that the carboxyl group in (II) forms neither of the
Figure 1
The molecule of compound (I), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 30% probability level.
Figure 4
Part of the crystal structure of (I), showing the formation of a
Figure 2
The molecule of compound (II), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 30% probability level.
2
centrosymmetric R (8) dimer. Atoms marked with an asterisk (*) are
at the symmetry position (1 � x, 1 � y, 1 � z).
2
ꢁ
Acta Cryst. (2004). C60, o120±o124
Christopher Glidewell et al.
Isomers and polymorphs of C14
H
10
N O
2 5
o121

organic compounds
asymmetric unit (Fig. 3) and, in a similar fashion, carboxyl
atom O11B in the type B molecule at (x, y, z) acts as
hydrogen-bond donor to amidic atom O17A in the type A
molecule at (x, 1 + y, z). These two hydrogen bonds thus
2
generate by translation a C (14) chain running parallel to the
2
[
010] direction (Fig. 7). These translational chains are then
bl i on nk de ds . into (001) sheets by the two NÐHÁ Á ÁO hydrogen
Amino atom N1A in the type A molecule at (x, y, z) acts as
hydrogen-bond donor to carboxyl atom O12B in the type B
1
2
1
2
1
2
2
2
molecule at ( � x, y � , � z), so producing a second C (14)
Figure 5
Stereoview of part of the crystal structure of (I), showing the linking of
the hydrogen-bonded dimers into an (010) sheet by means of aromatic
ꢀ±ꢀ stacking interactions. For the sake of clarity, H atoms bonded to C or
N atoms have been omitted.
Figure 7
Part of the crystal structure of (III), showing the C (14) chain generated
2
2
by translation. For the sake of clarity, H atoms bonded to C atoms have
been omitted. Atoms marked with an asterisk (*) or hash (#) are at the
symmetry positions (x, 1 + y, z) and (x, y � 1, z), respectively.
Figure 6
Stereoview of part of the crystal structure of (II), showing the formation
4
4
of an (001) sheet of R (22) rings. For the sake of clarity, H atoms bonded
to C atoms have been omitted.
the different functional groups (acid and amide) within the
molecule.
The combination of the two C(7) chains in (II) generates an
(
(
001) sheet in the form of a hydrogen-bonded (4,4)-net
4
Batten & Robson, 1998) built from a single type of R (22)
4
ring (Fig. 6). This sheet lies in the domain � 0.03 < z < 0.53 and
a second such sheet lies in the domain 0.47 < z < 1.03, but there
are no direction-speci®c interactions between adjacent sheets.
The supramolecular structure of the monoclinic form, (III),
consists of sheets generated by a combination of OÐHÁ Á ÁO
and NÐHÁ Á ÁO hydrogen bonds, linked into a three-dimen-
sional framework by a single rather strong CÐHÁ Á ÁO
hydrogen bond (Table 6). Carboxyl atom O11A acts as
hydrogen-bond donor to amidic atom O17B within the
Figure 8
Stereoview of part of the crystal structure of (III), showing the C (14)
2
2
1
1
1
4 4
chains generated by translation and by the 2 screw axis along ( , y, ). For
the sake of clarity, H atoms bonded to C atoms have been omitted.
ꢁ
o122 Christopher Glidewell et al.
10 2
Isomers and polymorphs of C14H N O
5
Acta Cryst. (2004). C60, o120±o124

organic compounds
chain parallel to [010], this time generated by the 2 screw axis
1
Table 1
Selected geometric parameters (A, ) for (I).
Ê
ꢀ
1
1
along ( , y, ) (Fig. 8). Similarly, amino atom N1B at (x, y, z)
3
4
4
acts as hydrogen-bond donor to carboxyl atom O12A at ( � x,
2
C18ÐO11
1.312 (2)
C18ÐO12
1.227 (2)
1
2
1
2
2
+
y, � z), so producing a third C (14) chain, this time
3 1
1
2
generated by the 2 screw axis along ( , y, ).
4
4
C12ÐC11ÐC17ÐN1
C11ÐC17ÐN1ÐC21
C17ÐN1ÐC21ÐC22
127.5 (2)
177.8 (2)
� 139.1 (2)
C11ÐC12ÐC18ÐO11
C21ÐC22ÐN22ÐO21
153.6 (2)
143.3 (2)
2
2
The combination of these three C (14) chains generates an
(001) sheet lying in the domain � 0.02 < z < 0.52, and a second
such sheet, related to the ®rst by inversion, lies in the domain
0
.48 < z < 1.02. The sheet is reinforced by a CÐHÁ Á ÁO
Table 2
Hydrogen-bonding geometry (A, ) for (I).
hydrogen bond (Table 6) and adjacent sheets are linked by a
second CÐHÁ Á ÁO hydrogen bond. Atom C23B in the type B
molecule at (x, y, z), which lies in the � 0.02 < z < 0.52 sheet,
acts as hydrogen-bond donor to nitro atom O41A in the type
ꢀ
Ê
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
N1ÐH1Á Á ÁO22
0.88
0.84
2.14
1.78
2.719 (2)
2.623 (2)
123
178
1
1
1
i
A molecule at ( + x, � y, + z), which forms part of the
O11ÐH11Á Á ÁO12
2
2
2
sheet in the domain 0.48 < z < 1.02. Propagation of this
interaction by the space group then generates a single three-
dimensional framework.
Symmetry code: (i) 1 � x; 1 � y; 1 � z.
Compound (II)
Crystal data
Experimental
C
14
10
H N
O
2 5
Mo Kꢁ radiation
Samples of both acids were prepared by heating under re¯ux
chloroform solutions containing equimolar mixtures of phthalic
anhydride and the appropriate nitroaniline. The reactions were
monitored by thin-layer chromatography and, when complete, the
mixtures were cooled and the solvent was removed. Crystals suitable
for single-crystal X-ray diffraction were grown by slow evaporation of
solutions in ethanol for (I) and (II), and in acetone for (III). Melting
points: for (I), 426±428 K; for (II), 475±477 K, with liberation of
water, followed rapidly by re-solidi®cation on formation of N-(4-
nitrophenyl)phthalimide and subsequent re-melting at 528±531 K; for
M
r
= 286.24
Orthorhombic, P2 2 2
1 1
Cell parameters from 1820
re¯ections
1
Ê
ꢀ
a = 3.9188 (2) A
b = 12.6896 (6) A
c = 27.7029 (16) A
Ê
V = 1377.61 (12) A
ꢂ = 3.2±27.5
Ê
� 1
ꢃ = 0.11 mm
T = 120 (2) K
Ê
3
Needle, colourless
0.25 Â 0.08 Â 0.04 mm
Z = 4
D = 1.380 Mg m
�
3
x
Data collection
Nonius KappaCCD area-detector
diffractometer
1820 independent re¯ections
1237 re¯ections with I > 2ꢅ(I)
(III), 471±473 K, with liberation of water, followed rapidly by re-
solidi®cation as for (II).
'
scans, and ! scans with ꢄ offsets
Absorption correction: multi-scan
SORTAV; Blessing, 1995, 1997)
min = 0.969, Tmax = 0.996
Rint = 0.052
ꢀ
ꢂ
max = 27.5
(
T
h = � 5 ! 5
k = � 16 ! 16
l = � 35 ! 35
Compound (I)
4875 measured re¯ections
Re®nement
Crystal data
2
Re®nement on F
2
H-atom parameters constrained
C
14
H
10
N
2
O
5
Mo Kꢁ radiation
Cell parameters from 2848
re¯ections
2
2
2
2
R[F > 2ꢅ(F )] = 0.055
wR(F ) = 0.123
w = 1/[ꢅ (F
where P = (F
(Á/ꢅ)max < 0.001
Áꢆmax = 0.21 e A
Áꢆmin = � 0.21 e AÊ
o
) + (0.0583P) ]
+ 2F )/3
o c
r
M = 286.24
Orthorhombic, Pbca
Ê
a = 7.2761 (2) A
2
2 2
ꢀ
S = 1.09
1820 re¯ections
191 parameters
ꢂ = 3.2±27.5
ꢃ = 0.12 mm
T = 120 (2) K
Ê
� 3
Ê
� 1
b = 14.8881 (5) A
� 3
Ê
c = 23.0407 (6) A
Ê
V = 2495.94 (13) A
3
Block, colourless
0.36 Â 0.36 Â 0.22 mm
Z = 8
�
x
D = 1.523 Mg m
3
Table 3
Selected geometric parameters (A, ) for (II).
Ê
ꢀ
Data collection
C18ÐO11
1.324 (3)
C18ÐO12
1.219 (3)
Nonius KappaCCD area-detector
diffractometer
2848 independent re¯ections
1876 re¯ections with I > 2ꢅ(I)
C12ÐC11ÐC17ÐN1
C11ÐC17ÐN1ÐC21
C17ÐN1ÐC21ÐC22
� 64.8 (5)
179.1 (3)
17.7 (6)
C11ÐC12ÐC18ÐO11
C23ÐC24ÐN24ÐO41
171.2 (3)
168.8 (4)
'
scans, and ! scans with ꢄ offsets
Absorption correction: multi-scan
SORTAV; Blessing, 1995, 1997)
min = 0.955, Tmax = 0.975
5 224 measured re¯ections
Rint = 0.072
ꢀ
ꢂ
max = 27.5
(
T
h = � 7 ! 9
k = � 19 ! 19
l = � 27 ! 29
1
Table 4
Hydrogen-bonding geometry ( AÊ , ) for (II).
ꢀ
Re®nement
2
Re®nement on F
2
H-atom parameters constrained
2
2
2
2
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
R[F > 2ꢅ(F )] = 0.049
wR(F ) = 0.115
S = 0.98
w = 1/[ꢅ (F
where P = (F
(Á/ꢅ)max = 0.001
Áꢆmax = 0.24 e A
Áꢆmin = � 0.29 e AÊ
o
) + (0.0595P) ]
+ 2F )/3
o c
2
2 2
i
N1ÐH1Á Á ÁO12
0.88
0.84
1.96
1.78
2.833 (3)
2.614 (3)
171
173
ii
� 3
O11ÐH11Á Á ÁO17
Symmetry codes: (i) x � 1; y; z; (ii) 2 � x; ‡ y; � z.
Ê
2
1
848 re¯ections
91 parameters
� 3
1
2
3
2
ꢁ
Acta Cryst. (2004). C60, o120±o124
Christopher Glidewell et al.
Isomers and polymorphs of C14
H
10
N O
2 5
o123

organic compounds
lents were merged. Conventional re®nement of (II) led to R = 0.095
� 3
Compound (III)
Ê
with a maximum residual density of 1.63 e A , and examination of
the re®ned structure of (II) using PLATON (Spek, 2003) revealed
Crystal data
�
3
Ê
two voids, each of volume ca 89 A , centred at approximately (0, , )
4 2
3
1 1
C
H
14 10
N O
2 5
D
x
= 1.474 Mg m
M
r
= 286.24
Mo Kꢁ radiation
Cell parameters from 5503
re¯ections
3
and (0, , 0). The electron density within these voids could not be
4
Monoclinic, P2 =n
1
interpreted in terms of any sensible model of solvent molecules, and
accordingly the re¯ection data were subjected to the SQUEEZE
option in PLATON before the ®nal re®nement. This procedure
suggested the presence of only 6±7 electrons per unit cell within the
voids. Examination of the re®ned structure of (III) using PLATON
also revealed two symmetry-related void spaces per unit cell, each of
Ê
a = 10.2098 (10) A
Ê
ꢀ
b = 9.3749 (8) A
ꢂ = 3.0±27.4
ꢃ = 0.11 mm
T = 120 (2) K
Ê
� 1
c = 27.409 (2) A
ꢀ
Ê
ꢇ = 100.578 (4)
V = 2578.9 (4) A
Z = 8
3
Plate, colourless
0.22 Â 0.18 Â 0.10 mm
Ê
approximate volume 63 A , centred at (0, , 0) and ( , 0, ), although
2 2 2
3
1
1
1
Data collection
the residual densities from the re®nement were very low. Accord-
ingly, a supernumerary O atom was placed near the centre of the void
and its site-occupancy factor was re®ned, giving a value of 0.045 (6),
indicative of negligible electron density within the void.
Nonius KappaCCD area-detector
diffractometer
5503 independent re¯ections
2662 re¯ections with I > 2ꢅ(I)
'
scans, and ! scans with ꢄ offsets
Absorption correction: multi-scan
SORTAV; Blessing, 1995, 1997)
min = 0.965, Tmax = 0.989
9 240 measured re¯ections
Rint = 0.095
ꢀ
ꢂ
max = 27.4
(
T
h = � 11 ! 12
k = � 12 ! 11
l = � 35 ! 35
For all three compounds, data collection: KappaCCD Server
Software (Nonius, 1997); cell re®nement: DENZO±SMN (Otwin-
1
owski
& Minor, 1997); data reduction: DENZO±SMN. For
Re®nement
compounds (I) and (II), program(s) used to solve structure:
SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure:
SHELXL97 (Sheldrick, 1997). For compound (III), program(s) used
to solve structure: OSCAIL (McArdle, 2003) and SHELXS97;
program(s) used to re®ne structure: OSCAIL and SHELXL97. For
all three compounds, molecular graphics: PLATON (Spek, 2003);
software used to prepare material for publication: SHELXL97 and
PRPKAPPA (Ferguson, 1999).
2
Re®nement on F
2
H-atom parameters constrained
2
2
2
2
R[F > 2ꢅ(F )] = 0.069
wR(F ) = 0.166
S = 0.99
w = 1/[ꢅ (F
where P = (F
(Á/ꢅ)max < 0.001
Áꢆmax = 0.30 e A
Áꢆmin = � 0.26 e AÊ
o
) + (0.0716P) ]
+ 2F )/3
o c
2
2 2
Ê
� 3
5
3
503 re¯ections
81 parameters
� 3
Table 5
Selected geometric parameters (A, ) for (III).
Ê
ꢀ
X-ray data were collected at the EPSRC X-ray Crystal-
lographic Service, University of Southampton, England; the
authors thank the staff for all their help and advice. JNL
thanks NCR Self-Service, Dundee, for grants which have
provided computing facilities for this work. JLW thanks CNPq
and FAPERJ for ®nancial support.
C18AÐO11A
C18AÐO12A
1.321 (3)
1.219 (3)
C18BÐO11B
C18BÐO12B
1.324 (3)
1.213 (3)
C12AÐC11AÐC17AÐN1A� 85.3 (4)
C11AÐC17AÐN1AÐC21A 172.5 (3)
C17AÐN1AÐC21AÐC22A� 26.3 (4)
C12BÐC11BÐC17BÐN1B � 88.7 (4)
C11BÐC17BÐN1BÐC21B 176.7 (3)
C17BÐN1BÐC21BÐC22B 10.8 (5)
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: GG1204). Services for accessing these data are
described at the back of the journal.
Table 6
Hydrogen-bonding geometry (A, ) for (III).
Ê
ꢀ
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
References
i
N1AÐH1AÁ Á ÁO12B
0.88
0.88
0.84
0.84
0.95
2.09
2.16
1.84
1.83
2.45
2.873 (4)
2.902 (3)
2.664 (3)
2.666 (3)
3.355 (4)
147
141
166
174
160
Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed. 37, 1460±1494.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.
Int. Ed. Engl. 34, 1555±1573.
Blessing, R. H. (1995). Acta Cryst. A51, 33±38.
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421±426.
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.
Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst.
C59, o509±o511.
ii
N1BÐH1BÁ Á ÁO12A
O11AÐH11AÁ Á ÁO17B
iii
O11BÐH11BÁ Á ÁO17A
iv
C23BÐH23BÁ Á ÁO41A
1
2
1
2
1
2
3
2
1
2
1
2
Symmetry codes: (i) � x; y �
;
� z; (ii) � x; ‡ y; � z; (iii) x; 1 ‡ y; z; (iv)
1
2
1
2
1
2
‡
x; � y; ‡ z.
McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography
Centre, Chemistry Department, NUI Galway, Ireland.
Nonius (1997). KappaCCD Server Software. Windows 3.11 Version. Nonius
BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M.
Sweet, pp. 307±326. New York: Academic Press.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
G oÈ ttingen, Germany.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7±13.
For compounds (I), (II) and (III), the space groups Pbca, P2
and P2 /n, respectively, were uniquely assigned from the systematic
absences. All H atoms were located from difference maps and then
1 1 1
2 2
1
Ê
treated as riding atoms, with distances CÐH = 0.95 A, NÐH = 0.88 A
Ê
Ê
and OÐH = 0.84 A. In the absence of signi®cant anomalous scat-
tering, the absolute con®guration of (II) could not be established.
However, this has no chemical signi®cance and the Friedel equiva-
ꢁ
o124 Christopher Glidewell et al.
10 2
Isomers and polymorphs of C14H N O
5
Acta Cryst. (2004). C60, o120±o124