3-(3-Nitrophenylaminocarbonyl)propionic acid: Hydrogen-bonded sheets of alternating R22(8) and R66(36) rings

Article abstract of DOI:10.1107/S0108270105040229

Molecules of the title compound, C₁₀H₁₀N ₂O₅, are linked by a combination of O - H...O and N - H...O hydrogen bonds into (100) sheets containing alternating R ₂²(8) and R₆^6<

Full text of DOI:10.1107/S0108270105040229

organic compounds
parts of the R22(8) dimers centred at (21, 0, 0) and (12, 1, 1),
respectively. Similarly, atoms O1 at (x, y, z) and (1 x, 1 y,
Acta Crystallographica Section C
Crystal Structure
Communications
1
z) accept hydrogen bonds from atoms N1 at (x, 12 y, 21 + z)
ISSN 0108-2701
and (1 x, 12 + y, 12 z), which are pairs of the dimers centred,
respectively, at (12, 0, 1) and (12, 1, 0). In this manner, each dimer
3-(3-Nitrophenylaminocarbonyl)-
propionic acid: hydrogen-bonded
sheets of alternating R22(8) and R66(36)
rings
James L. Wardell,a Janet M. S. Skakle,b John N. Lowb and
Christopher Glidewellc*
a
Â
Â
Ã
Instituto de Quõmica, Departamento de Quõmica Inorganica, Universidade Federal
do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil, bDepartment of Chemistry,
University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and
cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
Correspondence e-mail: cg@st-andrews.ac.uk
Received 1 December 2005
Accepted 2 December 2005
Online 24 December 2005
Molecules of the title compound, C10H10N2O5, are linked by
a combination of OÐHÁ Á ÁO and NÐHÁ Á ÁO hydrogen
bonds into (100) sheets containing alternating R22(8) and
R66(36) rings.
is directly linked to four other dimers via the amidic C(4)
chains along [001], so forming a (100) sheet in which centro-
symmetric R22(8) and R66(36) rings alternate in a chessboard
fashion (Fig. 3).
Comment
The reaction of C-substituted anilines, such as nitroanilines,
with succinic anhydride yields initially 3-(arylaminocarbon-
yl)propionic acids, (A) (see scheme), dehydration of which
yields the corresponding N-arylsuccinimides, (B). We have
recently reported the molecular and supramolecular struc-
tures of the three isomeric N-(nitrophenyl)succinimides (B),
where R = NO2 (Glidewell et al., 2005). We have now prepared
all three isomeric 3-(nitrophenylaminocarbonyl)propionic
acids (A), where R = NO2, but unfortunately only the 3-nitro
isomer has provided crystals suitable for single-crystal struc-
ture determination. We report here the molecular and
supramolecular structures of 3-(3-nitrophenylaminocarbon-
yl)propionic acid, (I).
The molecules of (I) (Fig. 1) are linked into sheets by a
combination of an NÐHÁ Á ÁO C hydrogen bond, forming the
usual amidic C(4) chain, and an OÐHÁ Á ÁO hydrogen bond,
forming the usual centrosymmetric R22(8) (Bernstein et al.,
1995) motif characteristic of simple carboxylic acids (Table 1).
Carboxyl atom O43 in the molecule at (x, y, z) acts as a
hydrogen-bond donor to atom O44 in the molecule at (1 x,
1
y, 1 z), so that the reference R22(8) dimer is centred at
(12, 12, 12 ) (Fig. 2). Amide atoms N1 at (x, y, z) and (1 x, 1 y,
z), which form part of the dimer centred at (12, 21, 21 ), act as
1
Figure 1
The molecule of (I), showing the atom-labelling scheme. Displacement
ellipsoids are drawn at the 30% probability level.
hydrogen-bond donors to amide atoms O1 at (x, 12 y, 21 + z)
and (1 x, 12 + y, 32 z), respectively, which themselves form
Acta Cryst. (2006). C62, o45±o46
DOI: 10.1107/S0108270105040229
# 2006 International Union of Crystallography o45

organic compounds
Crystal data
3
C10H10N2O5
Mr = 238.20
Dx = 1.441 Mg m
Mo Kꢁ radiation
Monoclinic, P21=c
Cell parameters from 2525
re¯ections
Ê
a = 6.6765 (4) A
ꢂ = 2.1±27.6ꢀ
Ê
b = 19.7961 (13) A
1
Ê
c = 9.0675 (5) A
ꢃ = 0.12 mm
T = 293 (2) K
ꢀ = 113.595 (4)ꢀ
V = 1098.25 (11) A
Z = 4
3
Ê
Plate, colourless
0.38 Â 0.17 Â 0.04 mm
Data collection
Bruker SMART 1000 CCD area-
detector diffractometer
! scans
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
Tmin = 0.967, Tmax = 0.995
9375 measured re¯ections
2525 independent re¯ections
1537 re¯ections with I > 2ꢄ(I)
Rint = 0.038
ꢂmax = 27.6ꢀ
h = 8 ! 8
k = 25 ! 25
l = 11 ! 9
Re®nement
Re®nement on F2
R[F2 > 2ꢄ(F2)] = 0.044
wR(F2) = 0.115
S = 0.91
2525 re¯ections
162 parameters
H-atom parameters constrained
w = 1/[ꢄ2(Fo2) + (0.0652P)2]
2
where P = (Fo + 2Fc2)/3
(Á/ꢄ)max < 0.001
3
Ê
Áꢅmax = 0.15 e A
3
Ê
0.22 e A
Áꢅmin
=
Table 1
Hydrogen-bond geometry (A, ).
ꢀ
Ê
Figure 2
DÐHÁ Á ÁA
DÐH
HÁ Á ÁA
DÁ Á ÁA
DÐHÁ Á ÁA
Part of the crystal structure of (I), showing the formation of an R22(8)
dimer centred at (12, , 21 ). Atoms marked with an asterisk (*) are at the
1
N1ÐH1Á Á ÁO1i
0.89
0.82
1.96
1.84
2.850 (2)
2.654 (2)
173
175
2
symmetry position (1 x, 1 y, 1 z).
O43ÐH43Á Á ÁO44ii
Symmetry codes: (i) x; y ‡ 12; z 21; (ii) x ‡ 1; y ‡ 1; z ‡ 1.
The space group P21/c was uniquely assigned from the systematic
absences. All H atoms were located from difference maps and then
treated as riding atoms, with CÐH distances of 0.93 (aromatic) or
Ê
Ê
0.97 A (CH2), an NÐH distance of 0.89 A, and an OÐH distance of
Ê
0.82 A, and with Uiso(H) = 1.2Ueq(C,N,O).
Data collection: SMART (Bruker, 2000); cell re®nement: SAINT-
Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to
solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to
re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
PLATON (Spek, 2003); software used to prepare material for
publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).
The authors thank the University of Aberdeen for funding
the purchase of the diffractometer. JLW thanks CNPq and
FAPERJ for ®nancial support.
Figure 3
A stereoview of part of the crystal structure of (I), showing the formation
of a (100) sheet built from R22(8) and R66(36) rings.
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: SK1893). Services for accessing these data are
described at the back of the journal.
References
Experimental
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.
Int. Ed. Engl. 34, 1555±1573.
A solution containing equimolar quantities of succinic anhydride and
3-nitroaniline (2 mmol of each) in 1,2-dichloroethane (20 ml) was
heated under re¯ux for 1 h and then left overnight at room
temperature. The solvent was removed under reduced pressure and
the resulting solid product was recrystallized from ethanol (m.p. 455±
457 K). IR (KBr): 3400±2000 (br), 1706, 1673, 1524, 1556, 1524, 1481,
Bruker (2000). SMART (Version 5.624), SAINT-Plus (Version 6.02A) and
SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA.
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.
Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst.
C61, o216±o220.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
GoÈttingen, Germany.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7±13.
1434, 1403, 1351, 1257, 1237, 1179, 1089, 1064, 993, 952, 891, 868,847,
1
819, 806, 737, 684, 670, 606, 540, 421, 498 cm
.
ꢁ
o46 Wardell et al.
C10H10N2O5
Acta Cryst. (2006). C62, o45±o46