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organic compounds
4-(2-Hydroxyethyl)anilinium 3,5-dinitrobenzoate
aSchool of Physical and Chemical Sciences, Queensland University of Technology, GPO Box 2434, Brisbane, Qld 4001, Australia
*Correspondence e-mail: g.smith@qut.edu.au
In the title compound, C8H12NO+·C7H3N2O6−, the anilinium and hydroxyl protons of the cation result in N—H⋯O, N—H⋯(O,O) and O—H⋯O hydrogen-bonding interactions with carboxylate O-atom acceptors, forming a two-dimensional network structure. An intermolecular C—H⋯O interaction is also present.
Related literature
For related structures, see: Etter & Frankenbach (1989); Lynch et al. (1991a
,b
, 1992
, 1993
); Ranganathan & Pedireddi (1998
); Aakeröy et al. (2003
); Hosomi et al. (2000
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: CrysAlis Pro (Oxford Diffraction, 2009); cell CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SIR92 (Altomare et al., 1994
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: PLATON (Spek, 2009
); software used to prepare material for publication: PLATON.
Supporting information
10.1107/S1600536809030426/bt5012sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809030426/bt5012Isup2.hkl
The title compound was synthesized by heating together 1 mmol quantities of 2-(4-aminophenyl)ethanol with 3,5-dinitrobenzoic acid in 50 ml of 50% ethanol–water under reflux for 10 minutes. After concentration to ca 30 ml, partial room temperature evaporation of the hot-filtered solution gave light brown coloured flat prisms (m.p. 389 K).
Hydrogen atoms involved in hydrogen-bonding interactions were located by difference methods and their positional and isotropic displacement parameters were refined. The H-atoms bonded to C were included in the
in calculated positions [C–H(aliphatic) = 0.97 Å and C–H(aromatic) = 0.93 Å) using a riding model approximation, with Uiso(H) = 1.2Ueq(C).Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell
CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).C8H12NO+·C7H3N2O6− | F(000) = 728 |
Mr = 349.30 | Dx = 1.480 Mg m−3 |
Monoclinic, P21/n | Melting point: 389 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 15.9566 (19) Å | Cell parameters from 3103 reflections |
b = 5.7844 (5) Å | θ = 3.0–28.9° |
c = 17.4118 (14) Å | µ = 0.12 mm−1 |
β = 102.811 (10)° | T = 297 K |
V = 1567.1 (3) Å3 | Cut block, pale brown |
Z = 4 | 0.30 × 0.30 × 0.25 mm |
Oxford Diffraction Gemini-S CCD-detector diffractometer | 3061 independent reflections |
Radiation source: Enhance (Mo) X-ray source | 2203 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 26.0°, θmin = 3.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→19 |
Tmin = 0.950, Tmax = 0.980 | k = −4→7 |
5928 measured reflections | l = −21→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0603P)2] where P = (Fo2 + 2Fc2)/3 |
3061 reflections | (Δ/σ)max < 0.001 |
242 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C8H12NO+·C7H3N2O6− | V = 1567.1 (3) Å3 |
Mr = 349.30 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.9566 (19) Å | µ = 0.12 mm−1 |
b = 5.7844 (5) Å | T = 297 K |
c = 17.4118 (14) Å | 0.30 × 0.30 × 0.25 mm |
β = 102.811 (10)° |
Oxford Diffraction Gemini-S CCD-detector diffractometer | 3061 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2203 reflections with I > 2σ(I) |
Tmin = 0.950, Tmax = 0.980 | Rint = 0.017 |
5928 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | Δρmax = 0.21 e Å−3 |
3061 reflections | Δρmin = −0.17 e Å−3 |
242 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 | ||
O11A | 0.46281 (7) | 0.8636 (2) | 0.32392 (7) | 0.0479 (4) | |
N4A | 0.09143 (8) | 0.6731 (3) | 0.07459 (9) | 0.0423 (4) | |
C1A | 0.33713 (9) | 0.9649 (3) | 0.17095 (8) | 0.0376 (5) | |
C2A | 0.32916 (10) | 0.7560 (3) | 0.13049 (10) | 0.0468 (5) | |
C3A | 0.24921 (10) | 0.6600 (3) | 0.09931 (10) | 0.0458 (5) | |
C4A | 0.17646 (9) | 0.7749 (2) | 0.10760 (8) | 0.0343 (4) | |
C5A | 0.18206 (9) | 0.9815 (3) | 0.14700 (9) | 0.0423 (5) | |
C6A | 0.26212 (10) | 1.0747 (3) | 0.17881 (10) | 0.0435 (5) | |
C21A | 0.49028 (10) | 0.9216 (3) | 0.25331 (10) | 0.0541 (6) | |
C31A | 0.42384 (9) | 1.0756 (3) | 0.20306 (10) | 0.0493 (5) | |
O11 | 0.04161 (6) | −0.00501 (19) | −0.08313 (7) | 0.0524 (4) | |
O12 | 0.10800 (7) | 0.31952 (19) | −0.03468 (7) | 0.0518 (4) | |
O31 | 0.42127 (8) | 0.3454 (2) | 0.01994 (9) | 0.0690 (5) | |
O32 | 0.48427 (7) | 0.1694 (2) | −0.06214 (8) | 0.0596 (4) | |
O51 | 0.34790 (7) | −0.5258 (2) | −0.18874 (7) | 0.0600 (4) | |
O52 | 0.21061 (8) | −0.5622 (2) | −0.20625 (7) | 0.0544 (4) | |
N3 | 0.42210 (8) | 0.2056 (2) | −0.03294 (8) | 0.0456 (5) | |
N5 | 0.27785 (8) | −0.4606 (2) | −0.17929 (7) | 0.0410 (4) | |
C1 | 0.19176 (8) | 0.0264 (2) | −0.07694 (8) | 0.0335 (4) | |
C2 | 0.26684 (9) | 0.1488 (2) | −0.04825 (8) | 0.0359 (5) | |
C3 | 0.34373 (9) | 0.0683 (3) | −0.06244 (9) | 0.0356 (4) | |
C4 | 0.34961 (9) | −0.1305 (2) | −0.10445 (9) | 0.0369 (4) | |
C5 | 0.27433 (9) | −0.2501 (2) | −0.13187 (8) | 0.0344 (4) | |
C6 | 0.19600 (9) | −0.1775 (2) | −0.11857 (8) | 0.0349 (4) | |
C11 | 0.10697 (9) | 0.1224 (3) | −0.06366 (9) | 0.0376 (5) | |
H2A | 0.37840 | 0.67910 | 0.12420 | 0.0560* | |
H3A | 0.24490 | 0.51900 | 0.07300 | 0.0550* | |
H5A | 0.13250 | 1.05830 | 0.15230 | 0.0510* | |
H6A | 0.26570 | 1.21390 | 0.20610 | 0.0520* | |
H11A | 0.4946 (13) | 0.751 (4) | 0.3511 (12) | 0.077 (7)* | |
H21A | 0.49730 | 0.78200 | 0.22460 | 0.0650* | |
H22A | 0.54520 | 1.00100 | 0.26650 | 0.0650* | |
H31A | 0.44640 | 1.13040 | 0.15900 | 0.0590* | |
H32A | 0.41540 | 1.20950 | 0.23400 | 0.0590* | |
H41A | 0.0919 (12) | 0.580 (3) | 0.0292 (12) | 0.069 (6)* | |
H42A | 0.0494 (13) | 0.788 (3) | 0.0611 (12) | 0.069 (6)* | |
H43A | 0.0745 (12) | 0.566 (3) | 0.1140 (12) | 0.074 (6)* | |
H2 | 0.26560 | 0.28400 | −0.01970 | 0.0430* | |
H4 | 0.40170 | −0.18130 | −0.11380 | 0.0440* | |
H6 | 0.14660 | −0.26430 | −0.13730 | 0.0420* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O11A | 0.0444 (6) | 0.0510 (7) | 0.0489 (7) | 0.0053 (5) | 0.0116 (5) | 0.0101 (6) |
N4A | 0.0347 (7) | 0.0486 (8) | 0.0425 (8) | −0.0028 (6) | 0.0065 (6) | −0.0058 (7) |
C1A | 0.0356 (8) | 0.0449 (9) | 0.0319 (8) | −0.0004 (7) | 0.0067 (6) | 0.0067 (7) |
C2A | 0.0335 (8) | 0.0548 (10) | 0.0541 (10) | 0.0072 (7) | 0.0141 (7) | −0.0055 (8) |
C3A | 0.0456 (9) | 0.0435 (9) | 0.0501 (10) | 0.0029 (7) | 0.0146 (8) | −0.0114 (8) |
C4A | 0.0328 (7) | 0.0388 (8) | 0.0308 (7) | −0.0001 (6) | 0.0063 (6) | 0.0004 (7) |
C5A | 0.0322 (8) | 0.0431 (9) | 0.0501 (10) | 0.0093 (7) | 0.0058 (7) | −0.0048 (8) |
C6A | 0.0443 (9) | 0.0371 (8) | 0.0469 (9) | 0.0024 (7) | 0.0057 (7) | −0.0059 (7) |
C21A | 0.0331 (8) | 0.0813 (12) | 0.0484 (10) | −0.0022 (8) | 0.0100 (7) | 0.0085 (9) |
C31A | 0.0380 (8) | 0.0643 (11) | 0.0455 (9) | −0.0075 (8) | 0.0092 (7) | 0.0108 (8) |
O11 | 0.0340 (6) | 0.0542 (7) | 0.0722 (8) | −0.0052 (5) | 0.0186 (6) | −0.0177 (6) |
O12 | 0.0423 (6) | 0.0502 (7) | 0.0635 (8) | 0.0051 (5) | 0.0130 (5) | −0.0216 (6) |
O31 | 0.0583 (8) | 0.0695 (9) | 0.0818 (10) | −0.0207 (6) | 0.0211 (7) | −0.0324 (8) |
O32 | 0.0366 (6) | 0.0669 (8) | 0.0808 (9) | −0.0044 (5) | 0.0251 (6) | −0.0015 (7) |
O51 | 0.0541 (7) | 0.0592 (8) | 0.0694 (8) | 0.0179 (6) | 0.0193 (6) | −0.0151 (6) |
O52 | 0.0585 (7) | 0.0490 (7) | 0.0551 (8) | −0.0050 (6) | 0.0111 (6) | −0.0155 (6) |
N3 | 0.0385 (7) | 0.0448 (8) | 0.0540 (9) | −0.0055 (6) | 0.0113 (6) | −0.0019 (7) |
N5 | 0.0487 (8) | 0.0381 (7) | 0.0366 (7) | 0.0082 (6) | 0.0102 (6) | −0.0009 (6) |
C1 | 0.0334 (7) | 0.0366 (8) | 0.0320 (7) | 0.0018 (6) | 0.0105 (6) | 0.0014 (6) |
C2 | 0.0399 (8) | 0.0343 (8) | 0.0353 (8) | 0.0011 (6) | 0.0124 (6) | −0.0031 (6) |
C3 | 0.0325 (7) | 0.0389 (8) | 0.0361 (8) | −0.0015 (6) | 0.0093 (6) | 0.0010 (7) |
C4 | 0.0341 (7) | 0.0410 (8) | 0.0381 (8) | 0.0058 (6) | 0.0136 (6) | 0.0029 (7) |
C5 | 0.0413 (8) | 0.0335 (7) | 0.0294 (7) | 0.0056 (6) | 0.0098 (6) | 0.0004 (6) |
C6 | 0.0338 (7) | 0.0362 (8) | 0.0343 (8) | −0.0013 (6) | 0.0069 (6) | −0.0019 (7) |
C11 | 0.0349 (8) | 0.0430 (9) | 0.0356 (8) | 0.0020 (7) | 0.0096 (6) | −0.0029 (7) |
O11A—C21A | 1.434 (2) | C5A—C6A | 1.384 (2) |
O11A—H11A | 0.89 (2) | C21A—C31A | 1.507 (2) |
O11—C11 | 1.2606 (19) | C2A—H2A | 0.9300 |
O12—C11 | 1.246 (2) | C3A—H3A | 0.9300 |
O31—N3 | 1.2277 (19) | C5A—H5A | 0.9300 |
O32—N3 | 1.2289 (18) | C6A—H6A | 0.9300 |
O51—N5 | 1.2249 (17) | C21A—H21A | 0.9700 |
O52—N5 | 1.2221 (18) | C21A—H22A | 0.9700 |
N4A—C4A | 1.474 (2) | C31A—H31A | 0.9700 |
N4A—H43A | 1.005 (19) | C31A—H32A | 0.9700 |
N4A—H41A | 0.958 (19) | C1—C2 | 1.3859 (19) |
N4A—H42A | 0.936 (19) | C1—C6 | 1.3939 (17) |
N3—C3 | 1.474 (2) | C1—C11 | 1.527 (2) |
N5—C5 | 1.4792 (17) | C2—C3 | 1.385 (2) |
C1A—C6A | 1.388 (2) | C3—C4 | 1.377 (2) |
C1A—C2A | 1.390 (2) | C4—C5 | 1.377 (2) |
C1A—C31A | 1.515 (2) | C5—C6 | 1.386 (2) |
C2A—C3A | 1.387 (2) | C2—H2 | 0.9300 |
C3A—C4A | 1.373 (2) | C4—H4 | 0.9300 |
C4A—C5A | 1.371 (2) | C6—H6 | 0.9300 |
C21A—O11A—H11A | 112.3 (13) | C1A—C6A—H6A | 119.00 |
C4A—N4A—H43A | 110.1 (11) | C31A—C21A—H21A | 110.00 |
H41A—N4A—H42A | 109.2 (17) | O11A—C21A—H22A | 110.00 |
H42A—N4A—H43A | 108.8 (17) | O11A—C21A—H21A | 110.00 |
C4A—N4A—H42A | 111.1 (12) | C31A—C21A—H22A | 110.00 |
H41A—N4A—H43A | 105.6 (15) | H21A—C21A—H22A | 108.00 |
C4A—N4A—H41A | 111.8 (12) | H31A—C31A—H32A | 107.00 |
O31—N3—O32 | 124.50 (14) | C1A—C31A—H31A | 108.00 |
O32—N3—C3 | 117.66 (13) | C1A—C31A—H32A | 108.00 |
O31—N3—C3 | 117.82 (13) | C21A—C31A—H31A | 108.00 |
O51—N5—O52 | 123.36 (13) | C21A—C31A—H32A | 108.00 |
O52—N5—C5 | 118.13 (12) | C2—C1—C6 | 118.82 (12) |
O51—N5—C5 | 118.50 (12) | C2—C1—C11 | 118.94 (12) |
C2A—C1A—C6A | 117.62 (14) | C6—C1—C11 | 122.23 (12) |
C6A—C1A—C31A | 120.48 (15) | C1—C2—C3 | 119.55 (12) |
C2A—C1A—C31A | 121.87 (14) | N3—C3—C2 | 118.25 (14) |
C1A—C2A—C3A | 121.28 (15) | N3—C3—C4 | 118.85 (13) |
C2A—C3A—C4A | 119.40 (15) | C2—C3—C4 | 122.88 (14) |
N4A—C4A—C3A | 119.50 (13) | C3—C4—C5 | 116.54 (13) |
N4A—C4A—C5A | 119.71 (13) | N5—C5—C4 | 117.97 (12) |
C3A—C4A—C5A | 120.79 (14) | N5—C5—C6 | 119.34 (12) |
C4A—C5A—C6A | 119.46 (15) | C4—C5—C6 | 122.66 (12) |
C1A—C6A—C5A | 121.45 (16) | C1—C6—C5 | 119.53 (12) |
O11A—C21A—C31A | 109.07 (13) | O11—C11—O12 | 125.45 (14) |
C1A—C31A—C21A | 115.58 (14) | O11—C11—C1 | 117.05 (14) |
C3A—C2A—H2A | 119.00 | O12—C11—C1 | 117.50 (13) |
C1A—C2A—H2A | 119.00 | C1—C2—H2 | 120.00 |
C2A—C3A—H3A | 120.00 | C3—C2—H2 | 120.00 |
C4A—C3A—H3A | 120.00 | C3—C4—H4 | 122.00 |
C4A—C5A—H5A | 120.00 | C5—C4—H4 | 122.00 |
C6A—C5A—H5A | 120.00 | C1—C6—H6 | 120.00 |
C5A—C6A—H6A | 119.00 | C5—C6—H6 | 120.00 |
O32—N3—C3—C2 | −161.49 (14) | C4A—C5A—C6A—C1A | 0.8 (2) |
O32—N3—C3—C4 | 16.9 (2) | O11A—C21A—C31A—C1A | −65.65 (18) |
O31—N3—C3—C2 | 19.7 (2) | C6—C1—C2—C3 | 0.9 (2) |
O31—N3—C3—C4 | −161.93 (14) | C11—C1—C2—C3 | −177.57 (13) |
O51—N5—C5—C4 | 3.63 (19) | C2—C1—C6—C5 | −1.49 (19) |
O52—N5—C5—C6 | 1.02 (18) | C11—C1—C6—C5 | 176.97 (13) |
O51—N5—C5—C6 | −178.10 (12) | C2—C1—C11—O11 | −172.71 (13) |
O52—N5—C5—C4 | −177.25 (13) | C2—C1—C11—O12 | 7.4 (2) |
C6A—C1A—C2A—C3A | −0.2 (2) | C6—C1—C11—O11 | 8.8 (2) |
C31A—C1A—C2A—C3A | −178.02 (15) | C6—C1—C11—O12 | −171.08 (13) |
C2A—C1A—C6A—C5A | −0.6 (2) | C1—C2—C3—N3 | 178.42 (13) |
C31A—C1A—C6A—C5A | 177.21 (15) | C1—C2—C3—C4 | 0.1 (2) |
C2A—C1A—C31A—C21A | −51.8 (2) | N3—C3—C4—C5 | −178.87 (13) |
C6A—C1A—C31A—C21A | 130.51 (16) | C2—C3—C4—C5 | −0.6 (2) |
C1A—C2A—C3A—C4A | 0.9 (3) | C3—C4—C5—N5 | 178.18 (13) |
C2A—C3A—C4A—C5A | −0.7 (2) | C3—C4—C5—C6 | 0.0 (2) |
C2A—C3A—C4A—N4A | −179.93 (16) | N5—C5—C6—C1 | −177.13 (12) |
N4A—C4A—C5A—C6A | 179.12 (14) | C4—C5—C6—C1 | 1.1 (2) |
C3A—C4A—C5A—C6A | −0.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O11A—H11A···O11i | 0.89 (2) | 1.88 (2) | 2.7569 (16) | 168 (2) |
N4A—H41A···O12 | 0.958 (19) | 1.924 (19) | 2.845 (2) | 160.8 (17) |
N4A—H42A···O11ii | 0.936 (19) | 2.02 (2) | 2.8905 (19) | 154.0 (18) |
N4A—H42A···O12ii | 0.936 (19) | 2.53 (2) | 3.1033 (18) | 119.9 (14) |
N4A—H43A···O11Aiii | 1.005 (19) | 1.783 (19) | 2.785 (2) | 174.4 (19) |
C5A—H5A···O11Aiv | 0.93 | 2.43 | 3.317 (2) | 161 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x, −y+1, −z; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C8H12NO+·C7H3N2O6− |
Mr | 349.30 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 297 |
a, b, c (Å) | 15.9566 (19), 5.7844 (5), 17.4118 (14) |
β (°) | 102.811 (10) |
V (Å3) | 1567.1 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.30 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini-S CCD-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.950, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5928, 3061, 2203 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.099, 0.98 |
No. of reflections | 3061 |
No. of parameters | 242 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.17 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O11A—H11A···O11i | 0.89 (2) | 1.88 (2) | 2.7569 (16) | 168 (2) |
N4A—H41A···O12 | 0.958 (19) | 1.924 (19) | 2.845 (2) | 160.8 (17) |
N4A—H42A···O11ii | 0.936 (19) | 2.02 (2) | 2.8905 (19) | 154.0 (18) |
N4A—H42A···O12ii | 0.936 (19) | 2.53 (2) | 3.1033 (18) | 119.9 (14) |
N4A—H43A···O11Aiii | 1.005 (19) | 1.783 (19) | 2.785 (2) | 174.4 (19) |
C5A—H5A···O11Aiv | 0.9300 | 2.4300 | 3.317 (2) | 161.00 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x, −y+1, −z; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x+1/2, y+1/2, −z+1/2. |
Acknowledgements
The authors acknowledge financial support from the Australian Research Council and the School of Physical and Chemical Sciences, Queensland University of Technology.
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The nitro-substituted aromatic acid, 3,5-dinitrobenzoic acid (3,5-DNBA) has been used to synthesize chiral crystalline adduct materials with physical properties potentially useful in applications such as nonlinear optics, giving e.g. the compound 3,5-DNBA–4-aminobenzoic acid (1/1) (Etter & Frankenbach, 1989). Since that time there have been a large number of 3,5-DNBA adduct structures reported, e.g. with indole-3-acetic acid (1:1) (Lynch et al., 1991a), phenoxyacetic acid (a 2:1 monohydrate) (Lynch et al., 1991b), 1,4-diiodobenzene (2:1) (Ranganathan & Pedireddi (1998)], a series of alkyl-substituted carbazoles (all 1:1) (Hosomi et al., 2000) and benzamide (1:1)] (Aakeröy et al., 2003); Proton-transfer compounds and proton-transfer-3,5-DNBA adduct compounds are also very common, e.g. with the herbicides amitrole (3-amino-1,2,4-triazole) and prometryn (N,N'-bis(1-methylethyl)-6- methylthio-1,2,4-triazine-2,4-diamide) (Lynch et al., 1993) (all 1:1)
In the light of this background we looked at 3,5-DNBA as a possible means of obtaining a crystalline compound from the non-crystalline aromatic Lewis base 2-(4-aminophenyl)ethanol. The 1:1 stoichiometric reaction of 3,5-DNBA with this reagent in 50% ethanol–water was expected to give either an anilinium salt or an adduct salt and the result was a 1:1 salt 4-(2-hydroxyethyl)anilinium 3,5-dinitrobenzoate C8H12NO+. C7H3N2O6- (I), the structure of which is reported here.
With (I) (Fig. 1), proton transfer occurs and the resulting anilinium group is subsequently involved in four hydrogen-bonding interactions with only carboxylate-O acceptors (Table 1). One of these associations is asymmetric cyclic [N–H···O,O', graph set R21(4)]. These interactions, together with an hydroxyl O–H···Ocarboxyl hydrogen bond give a two-dimensional network structure which lies in the (a0c) plane and extends down the b cell direction (Fig. 2). Also present in the structure are short inversion-related intermolecular nitro O···O nonbonding interactions [O32···O32iv, 2.8799 (18) Å; symmetry code: (iv) -x + 1, -y, -z]. The 3,5-DNBA anion is essentially planar [C2–C1–C11–O11A, -172.71 (13)° (carboxyl); C2–C3–N3–O32, -161.49 (14)° and C4–C5–N5–O52, -177.25 (13)° (nitro)].