organic compounds
Anilinium-3-carboxylate 3-carboxyanilinium nitrate
aDepartment of Chemistry, University of Engineering and Technology, Lahore 54890, Pakistan, bDepartment of Chemistry, Government College University, Lahore, Pakistan, and cDepartment of Physics, University of Sargodha, Sagrodha, Pakistan
*Correspondence e-mail: saeed_a786@hotmail.com
The title compound, C7H8NO2+·NO3−·C7H7NO2, exists in the form of a protonated dimer of two anilinium-3-carboxylate molecules related by an inversion center, and a nitrate anion located on a twofold rotation axis. The bridging H atom occupies, with equal probability, the two sites associated with the carboxyl atoms. In addition to the strong O—H⋯O hydrogen bond, in the crystal, the various units are linked via N—H⋯O and C—H⋯O hydrogen bonds forming a three-dimensional structure.
Related literature
For applications of aminobenzoic acids, see: Congiu et al. (2005); Swislocka et al. (2005). For related structures and details of their hydrogen-bonding motifs, see: Arora et al. (1973); Bahadur et al. (2007); Hansen et al. (2007); Lai & Marsh (1967); Lu et al. (2001); Smith et al. (1995); Zaidi et al. (2008).
Experimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S1600536812049392/kj2215sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049392/kj2215Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812049392/kj2215Isup3.cml
The title compound was prepared by adding one equivalent of 3-aminobenzoic acid (0.07 g) in 15 ml methanol to a solution of cerium nitrate (0.22 g, 0.5 mmol) in 15 ml me thanol. The brown solution was stirred for one hour, after which it was filtered and the filtrate was kept for crystallization at room temperature. The solution was covered with aluminium foil. After 3 days large orange-brown crystals were obtained (M.p. = 492 (1) K). A plate-shaped fragment cut from a large crystal was used for data collection.
The OH H atom was located in a difference Fourier map and refined freely with a fixed occupancy of 0.5. The NH3 atoms were located from a difference Fourier map and refined freely. The C—H atoms were placed in calculated positions and treated as riding atoms: C—H = 0.93 Å with Uiso(H) = 1.2Ueq(C).
Amino derivatives of benzoic acid are of considerable importance because of their use as anti-inflammatory and anticancer agents (Congiu et al., 2005). Benzoic acid, its derivatives and their complexes are also used as food preservatives and as antiseptic agents applied in various industrial branches: pharmaceutics, textile and cosmetics (Swislocka et al., 2005). In view of this interest, the crystal structures of various amino derivatives of benzoic acid (Hansen et al., 2007; Lai et al., 1967; Lu et al., 2001; Smith et al., 1995), and their ammonium salts (Arora et al., 1973; Bahadur et al., 2007; Zaidi et al., 2008), have been reported in the literature. The crystal structures of these compounds are characterized by strong hydrogen bonding.
The ammonium salts of 2-aminobenzoic acid are monomers (Bahadur et al., 2007; Zaidi et al., 2008), whereas the chloride salt of the anilinium-3-carboxylate ion (Arora et al., 1973) exists in the form of hydrogen-bonded dimers formed through the carboxylic acid groups of inversion related molecules. In the present study, we attempted to prepare a cerium(III) complex of 3-aminobenzoic acid but the resulting product was a simple nitrate salt of the acid. Herein, we present the
of this salt.In the title compound two anilinium-3-carboxylate molecules related by an inversion center are bound to a proton to form a protonated dimer through strong O—H···O hydrogen bonds (Fig. 1 and Table 1). A nitrate anion located on a 2-fold rotation axis is present as counter ion. The bridging H atom (H1O) occupies, with equal probability, the two sites associated with the carboxyl atoms, O1 and O1a [symmetry code: (a) = -x, -y + 2, -z]. The ammonium groups are involved in strong hydrogen bonds to the carbonyl as well as to the nitrate O atoms (Table 1).
In the crystal, (Fig. 2 and Table 1) molecules are linked via N—H..O and C—H..O hydrogen bonds forming a three-dimensional structure.
For applications of aminobenzoic acids, see: Congiu et al. (2005); Swislocka et al. (2005). For related structures and details of their hydrogen-bonding motifs, see: Arora et al. (1973); Bahadur et al. (2007); Hansen et al. (2007); Lai & Marsh (1967); Lu et al. (2001); Smith et al. (1995); Zaidi et al. (2008).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).Fig. 1. A view of the molecular structure of the title compound, with the atom numbering. Displacement ellipsoids are drawn at the 50% probability level. Atom H1O has an occupancy of 0.5 [symmetry codes: (a) = -x, -y + 2, -z; (b) -x + 1, y, -z + 1/2]. | |
Fig. 2. A view along the b axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines - see Table 1 for details [C-bound H atoms have been omitted for clarity]. |
C7H8NO2+·NO3−·C7H7NO2 | F(000) = 704 |
Mr = 337.29 | Dx = 1.562 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1777 reflections |
a = 16.0451 (3) Å | θ = 2.9–28.3° |
b = 4.7575 (1) Å | µ = 0.13 mm−1 |
c = 19.7143 (4) Å | T = 296 K |
β = 107.660 (1)° | Plate, pale orange |
V = 1433.96 (5) Å3 | 0.23 × 0.16 × 0.07 mm |
Z = 4 |
Bruker Kappa APEXII CCD area-detector diffractometer | 1777 independent reflections |
Radiation source: fine-focus sealed tube | 1604 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 28.3°, θmin = 3.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −20→21 |
Tmin = 0.525, Tmax = 0.806 | k = −6→6 |
6955 measured reflections | l = −26→24 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0497P)2 + 1.028P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
1777 reflections | Δρmax = 0.29 e Å−3 |
127 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0050 (11) |
C7H8NO2+·NO3−·C7H7NO2 | V = 1433.96 (5) Å3 |
Mr = 337.29 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 16.0451 (3) Å | µ = 0.13 mm−1 |
b = 4.7575 (1) Å | T = 296 K |
c = 19.7143 (4) Å | 0.23 × 0.16 × 0.07 mm |
β = 107.660 (1)° |
Bruker Kappa APEXII CCD area-detector diffractometer | 1777 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1604 reflections with I > 2σ(I) |
Tmin = 0.525, Tmax = 0.806 | Rint = 0.017 |
6955 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.29 e Å−3 |
1777 reflections | Δρmin = −0.20 e Å−3 |
127 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.03166 (6) | 0.8054 (2) | 0.04202 (5) | 0.0316 (3) | |
O2 | 0.11051 (6) | 0.75160 (18) | −0.03226 (4) | 0.0292 (3) | |
N1 | 0.38230 (6) | 0.2414 (2) | 0.11339 (6) | 0.0256 (3) | |
C1 | 0.09454 (7) | 0.6963 (2) | 0.02418 (6) | 0.0232 (3) | |
C2 | 0.15270 (7) | 0.4950 (2) | 0.07568 (6) | 0.0234 (3) | |
C3 | 0.23625 (7) | 0.4507 (2) | 0.07021 (6) | 0.0241 (3) | |
C4 | 0.29346 (7) | 0.2769 (2) | 0.11825 (6) | 0.0232 (3) | |
C5 | 0.26851 (8) | 0.1375 (3) | 0.17048 (6) | 0.0316 (3) | |
C6 | 0.18493 (9) | 0.1785 (3) | 0.17490 (7) | 0.0355 (4) | |
C7 | 0.12742 (8) | 0.3602 (3) | 0.12863 (7) | 0.0308 (3) | |
O3 | 0.44638 (8) | 0.7461 (2) | 0.20141 (6) | 0.0512 (4) | |
O4 | 0.50000 | 0.3567 (3) | 0.25000 | 0.0540 (5) | |
N2 | 0.50000 | 0.6216 (3) | 0.25000 | 0.0283 (4) | |
H1N | 0.3935 (11) | 0.384 (4) | 0.0864 (9) | 0.045 (4)* | |
H1O | 0.014 (2) | 0.953 (8) | 0.0144 (17) | 0.032 (8)* | 0.500 |
H2N | 0.3850 (11) | 0.075 (4) | 0.0881 (9) | 0.044 (4)* | |
H3 | 0.25330 | 0.53810 | 0.03430 | 0.0290* | |
H3N | 0.4235 (12) | 0.243 (3) | 0.1589 (10) | 0.043 (4)* | |
H5 | 0.30730 | 0.01800 | 0.20220 | 0.0380* | |
H6 | 0.16720 | 0.08300 | 0.20930 | 0.0430* | |
H7 | 0.07210 | 0.39160 | 0.13310 | 0.0370* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0287 (4) | 0.0321 (5) | 0.0368 (5) | 0.0116 (4) | 0.0142 (4) | 0.0065 (4) |
O2 | 0.0284 (4) | 0.0300 (5) | 0.0308 (4) | 0.0075 (3) | 0.0113 (3) | 0.0065 (3) |
N1 | 0.0214 (5) | 0.0265 (5) | 0.0268 (5) | 0.0049 (4) | 0.0040 (4) | 0.0010 (4) |
C1 | 0.0201 (5) | 0.0209 (5) | 0.0281 (5) | 0.0006 (4) | 0.0064 (4) | −0.0005 (4) |
C2 | 0.0222 (5) | 0.0215 (5) | 0.0257 (5) | 0.0022 (4) | 0.0059 (4) | −0.0005 (4) |
C3 | 0.0232 (5) | 0.0232 (5) | 0.0254 (5) | 0.0021 (4) | 0.0068 (4) | 0.0023 (4) |
C4 | 0.0214 (5) | 0.0223 (5) | 0.0247 (5) | 0.0023 (4) | 0.0050 (4) | −0.0022 (4) |
C5 | 0.0334 (6) | 0.0322 (6) | 0.0281 (6) | 0.0089 (5) | 0.0078 (5) | 0.0077 (5) |
C6 | 0.0390 (7) | 0.0392 (7) | 0.0321 (6) | 0.0062 (6) | 0.0164 (5) | 0.0117 (5) |
C7 | 0.0275 (6) | 0.0335 (6) | 0.0340 (6) | 0.0044 (5) | 0.0132 (5) | 0.0038 (5) |
O3 | 0.0579 (7) | 0.0333 (6) | 0.0462 (6) | 0.0102 (5) | −0.0086 (5) | 0.0069 (5) |
O4 | 0.0663 (10) | 0.0240 (7) | 0.0470 (9) | 0.0000 | −0.0196 (7) | 0.0000 |
N2 | 0.0291 (7) | 0.0251 (7) | 0.0286 (7) | 0.0000 | 0.0056 (6) | 0.0000 |
O1—C1 | 1.2753 (15) | C2—C3 | 1.3932 (17) |
O2—C1 | 1.2434 (14) | C2—C7 | 1.3865 (17) |
O1—H1O | 0.88 (4) | C3—C4 | 1.3769 (15) |
O3—N2 | 1.2283 (13) | C4—C5 | 1.3822 (17) |
O4—N2 | 1.260 (2) | C5—C6 | 1.384 (2) |
N1—C4 | 1.4671 (16) | C6—C7 | 1.386 (2) |
N1—H2N | 0.944 (18) | C3—H3 | 0.9300 |
N1—H3N | 0.939 (19) | C5—H5 | 0.9300 |
N1—H1N | 0.913 (18) | C6—H6 | 0.9300 |
C1—C2 | 1.4980 (15) | C7—H7 | 0.9300 |
C1—O1—H1O | 107 (2) | C2—C3—C4 | 119.60 (10) |
C4—N1—H3N | 110.7 (12) | C3—C4—C5 | 121.15 (11) |
H1N—N1—H2N | 105.5 (16) | N1—C4—C3 | 118.84 (10) |
C4—N1—H2N | 109.4 (11) | N1—C4—C5 | 120.01 (10) |
H2N—N1—H3N | 112.3 (14) | C4—C5—C6 | 118.98 (12) |
H1N—N1—H3N | 110.2 (15) | C5—C6—C7 | 120.73 (13) |
C4—N1—H1N | 108.6 (12) | C2—C7—C6 | 119.71 (12) |
O3i—N2—O4 | 118.83 (8) | C2—C3—H3 | 120.00 |
O3—N2—O4 | 118.83 (8) | C4—C3—H3 | 120.00 |
O3—N2—O3i | 122.34 (13) | C6—C5—H5 | 120.00 |
O2—C1—C2 | 119.12 (10) | C4—C5—H5 | 121.00 |
O1—C1—C2 | 117.10 (10) | C5—C6—H6 | 120.00 |
O1—C1—O2 | 123.76 (10) | C7—C6—H6 | 120.00 |
C3—C2—C7 | 119.77 (10) | C2—C7—H7 | 120.00 |
C1—C2—C3 | 117.42 (10) | C6—C7—H7 | 120.00 |
C1—C2—C7 | 122.79 (11) | ||
O1—C1—C2—C3 | −158.16 (10) | C3—C2—C7—C6 | −1.16 (18) |
O1—C1—C2—C7 | 20.10 (16) | C2—C3—C4—N1 | −177.64 (9) |
O2—C1—C2—C3 | 20.63 (15) | C2—C3—C4—C5 | 2.25 (16) |
O2—C1—C2—C7 | −161.12 (11) | N1—C4—C5—C6 | 178.75 (11) |
C1—C2—C3—C4 | 177.24 (9) | C3—C4—C5—C6 | −1.13 (18) |
C7—C2—C3—C4 | −1.08 (16) | C4—C5—C6—C7 | −1.2 (2) |
C1—C2—C7—C6 | −179.38 (11) | C5—C6—C7—C2 | 2.3 (2) |
Symmetry code: (i) −x+1, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O1ii | 0.88 (4) | 1.61 (4) | 2.4868 (13) | 171 (4) |
O1—H1O···O2ii | 0.88 (4) | 2.55 (3) | 3.0686 (14) | 118 (3) |
N1—H1N···O2iii | 0.913 (18) | 2.027 (19) | 2.9157 (13) | 164.2 (17) |
N1—H2N···O2iv | 0.944 (18) | 1.918 (18) | 2.8609 (13) | 177.0 (16) |
N1—H3N···O3v | 0.939 (19) | 2.498 (15) | 2.9220 (14) | 107.6 (11) |
N1—H3N···O3 | 0.939 (19) | 2.526 (15) | 2.9582 (14) | 108.3 (11) |
N1—H3N···O4 | 0.939 (19) | 1.920 (19) | 2.8345 (11) | 163.9 (13) |
C3—H3···O2iii | 0.93 | 2.41 | 3.1189 (15) | 132 |
C5—H5···O3v | 0.93 | 2.58 | 3.3058 (18) | 135 |
Symmetry codes: (ii) −x, −y+2, −z; (iii) −x+1/2, −y+3/2, −z; (iv) −x+1/2, −y+1/2, −z; (v) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C7H8NO2+·NO3−·C7H7NO2 |
Mr | 337.29 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 296 |
a, b, c (Å) | 16.0451 (3), 4.7575 (1), 19.7143 (4) |
β (°) | 107.660 (1) |
V (Å3) | 1433.96 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.23 × 0.16 × 0.07 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.525, 0.806 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6955, 1777, 1604 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.101, 1.07 |
No. of reflections | 1777 |
No. of parameters | 127 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.20 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O1i | 0.88 (4) | 1.61 (4) | 2.4868 (13) | 171 (4) |
O1—H1O···O2i | 0.88 (4) | 2.55 (3) | 3.0686 (14) | 118 (3) |
N1—H1N···O2ii | 0.913 (18) | 2.027 (19) | 2.9157 (13) | 164.2 (17) |
N1—H2N···O2iii | 0.944 (18) | 1.918 (18) | 2.8609 (13) | 177.0 (16) |
N1—H3N···O3iv | 0.939 (19) | 2.498 (15) | 2.9220 (14) | 107.6 (11) |
N1—H3N···O3 | 0.939 (19) | 2.526 (15) | 2.9582 (14) | 108.3 (11) |
N1—H3N···O4 | 0.939 (19) | 1.920 (19) | 2.8345 (11) | 163.9 (13) |
C3—H3···O2ii | 0.93 | 2.41 | 3.1189 (15) | 132 |
C5—H5···O3iv | 0.93 | 2.58 | 3.3058 (18) | 135 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1/2, −y+3/2, −z; (iii) −x+1/2, −y+1/2, −z; (iv) x, y−1, z. |
Acknowledgements
The authors are grateful to Government College University Lahore for providing the X-ray diffraction facility, and to Professor Helen Stoeckli-Evans for valuable discussions.
References
Arora, S. K., Sundaralingam, M., Dancz, J. S., Stanford, R. H. & Marsh, R. E. (1973). Acta Cryst. B29, 1849–1855. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Bahadur, S. A., Kannan, R. S. & Sridhar, B. (2007). Acta Cryst. E63, o2722–o2723. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Congiu, C., Cocco, M. T., Lilliu, V. & Onnis, V. (2005). J. Med. Chem. 48, 8245–8252. Web of Science CrossRef PubMed CAS Google Scholar
Hansen, L. K., Perlovich, G. L. & Bauer-Brandl, A. (2007). Acta Cryst. E63, o2361. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lai, T. F. & Marsh, R. E. (1967). Acta Cryst. 22, 885–893. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Lu, T. H., Chattopadhyay, P., Liao, F. L. & Lo, J.-M. (2001). Anal. Sci. 17, 905–906. CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Smith, G., Lynch, D. E., Byriel, K. A. & Kennard, C. H. L. (1995). Aust. J. Chem. 48, 1133–1149. CSD CrossRef CAS Web of Science Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Swislocka, R., Regulska, E., Samsonowicz, M., Hrynaszkiewicz, T. & Lewandowski, W. (2005). Spectrochim. Acta Part A, 61, 2966–2973. CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zaidi, S. A. R. A., Tahir, M. N., Iqbal, J. & Chaudhary, M. A. (2008). Acta Cryst. E64, o1957. Web of Science CSD CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Amino derivatives of benzoic acid are of considerable importance because of their use as anti-inflammatory and anticancer agents (Congiu et al., 2005). Benzoic acid, its derivatives and their complexes are also used as food preservatives and as antiseptic agents applied in various industrial branches: pharmaceutics, textile and cosmetics (Swislocka et al., 2005). In view of this interest, the crystal structures of various amino derivatives of benzoic acid (Hansen et al., 2007; Lai et al., 1967; Lu et al., 2001; Smith et al., 1995), and their ammonium salts (Arora et al., 1973; Bahadur et al., 2007; Zaidi et al., 2008), have been reported in the literature. The crystal structures of these compounds are characterized by strong hydrogen bonding.
The ammonium salts of 2-aminobenzoic acid are monomers (Bahadur et al., 2007; Zaidi et al., 2008), whereas the chloride salt of the anilinium-3-carboxylate ion (Arora et al., 1973) exists in the form of hydrogen-bonded dimers formed through the carboxylic acid groups of inversion related molecules. In the present study, we attempted to prepare a cerium(III) complex of 3-aminobenzoic acid but the resulting product was a simple nitrate salt of the acid. Herein, we present the crystal structure of this salt.
In the title compound two anilinium-3-carboxylate molecules related by an inversion center are bound to a proton to form a protonated dimer through strong O—H···O hydrogen bonds (Fig. 1 and Table 1). A nitrate anion located on a 2-fold rotation axis is present as counter ion. The bridging H atom (H1O) occupies, with equal probability, the two sites associated with the carboxyl atoms, O1 and O1a [symmetry code: (a) = -x, -y + 2, -z]. The ammonium groups are involved in strong hydrogen bonds to the carbonyl as well as to the nitrate O atoms (Table 1).
In the crystal, (Fig. 2 and Table 1) molecules are linked via N—H..O and C—H..O hydrogen bonds forming a three-dimensional structure.