organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
crystallizes in a monoclinic space group, P21, with unit-cell
dimensions very different from those of the orthorhombic
polymorph of (III), nonetheless forms a supramolecular
structure very similar to that of orthorhombic (III).
ISSN 0108-2701
In compound (II), the CÐO bond distances (Table 1) within
the carboxyl group are consistent with the location of the
carboxyl H atom as deduced from a difference map. The
torsion angles (Table 1 and Fig. 1) indicate that the molecules
of (II) have no internal symmetry and hence they are chiral.
Thus, in the absence of any inversion twinning, each crystal
will contain just a single enantiomorph of (II). However, this
chirality in the solid state has no chemical signi®cance.
The molecules of (II) (Fig. 1) are linked into sheets by a
combination of one NÐHÁ Á ÁO hydrogen bond and one OÐ
HÁ Á ÁO hydrogen bond, and the formation of the sheet is most
readily analysed in terms of the one-dimensional substructures
generated by the two individual hydrogen bonds.
2-(3-Nitrophenylaminocarbonyl)-
benzoic acid: hydrogen-bonded sheets
of R44(22) rings
Christopher Glidewell,a* John N. Low,b Janet M. S.
Skakleb and James L. Wardellc
aSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland,
bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen
c
Â
Â
AB24 3UE, Scotland, and Instituto de Quõmica, Departamento de Quõmica
Ã
Inorganica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ,
Amino atom N1 in the molecule at (x, y, z) acts as
hydrogen-bond donor to carboxyl atom O22 in the molecule at
( 1 + x, y, z), so generating by translation a C(7) (Bernstein et
al., 1995) chain running parallel to the [100] direction (Fig. 2).
Brazil
Correspondence e-mail: cg@st-andrews.ac.uk
Received 14 October 2005
Accepted 18 October 2005
Online 10 December 2005
In the title compound, C14H10N2O5, the molecules are linked
by a combination of one NÐHÁ Á ÁO and one OÐHÁ Á ÁO
hydrogen bond into sheets containing a single type of R44(22)
ring.
Comment
We recently reported the molecular and supramolecular
structures of 2-(2-nitrophenylaminocarbonyl)benzoic acid, (I),
and two polymorphs, one orthorhombic with space group
P212121 and the other monoclinic with space group P21/n, of
2-(4-nitrophenylaminocarbonyl)benzoic acid, (III) (Glidewell
et al., 2004). In the 2-nitro isomer, compound (I), the mol-
ecules form R22(8) carboxylic acid dimers, which are linked into
sheets by ꢀ±ꢀ stacking interactions, but intermolecular NÐ
HÁ Á ÁO hydrogen bonds are absent. In the orthorhombic
polymorph of the 4-nitro isomer, (III), the molecules are
linked into sheets of R44(22) rings built from a combination of
two C(7) chains, formed by NÐHÁ Á ÁO and OÐHÁ Á ÁO
hydrogen bonds, respectively. In the monoclinic polymorph of
(III), where Z0 = 2, the molecules are linked into a continuous
Figure 1
The molecule of compound (II), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 30% probability level.
Figure 2
three-dimensional framework by a combination of OÐHÁ Á ÁO,
NÐHÁ Á ÁO and CÐHÁ Á ÁO hydrogen bonds. We report here
the structure of the 3-nitro isomer, (II), which, although it
Part of the crystal structure of (II), showing the formation of a C(7) chain
along [100]. Atoms marked with an asterisk (*) or a hash (#) are at the
symmetry positions ( 1 + x, y, z) and (1 + x, y, z), respectively.
Acta Cryst. (2006). C62, o5±o7
DOI: 10.1107/S0108270105033512
# 2006 International Union of Crystallography o5
Glidewell, Christopher
