organic compounds
3-(1H-Imidazol-1-yl)propanaminium 2-carboxy-4,6-dinitrophenolate
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
*Correspondence e-mail: jjasinski@keene.edu
In the title salt, C6H12N3+·C7H3N2O7−, the imidazole ring is planar, with a maximum deviation of 0.0013 (14) Å for the N attached to the propanaminium group. In the anion, a single intramolecular O—H⋯O hydrogen bond is observed. The mean planes of the nitro groups in the anion are twisted from the benzene ring mean plane making dihedral angles of 24.7 (9) and 3.9 (6)°. In the crystal, the ammonium H atoms form N—H⋯N and N—H⋯O hydrogen bonds, resulting in an infinite chain along [111]. In addition to the classical hydrogen bonds, weak C—H⋯O and π–π [centroid–centroid distance = 3.7124 (9) Å] interactions are also observed, which lead to the formation a three-dimensional supramolecular structure that links the chains into layers along the bc plane.
CCDC reference: 986378
Related literature
For general background and the pharmacological properties of imidazole compounds, see: ten Have et al. (1997); Lombardino & Wiseman (1974); Jackson et al. (2000); Krezel (1998); Maier et al. (1989). For the related structures of substituted imidazoles, see: Dayananda et al. (2012); Hemamalini & Fun (2010); Jasinski et al. (2011); Wei et al. (2012); Yamuna et al. (2013).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supporting information
CCDC reference: 986378
10.1107/S1600536814003146/fj2659sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814003146/fj2659Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814003146/fj2659Isup3.cml
Commercially available 1-(3-aminopropyl)imidazole (0.5 g, 3.99 mmol) and 3,5 dinitrosalicylic acid (0.909 g, 3.99 mmol) were dissolved in 10 ml of methanol and stirred for 15 minutes at 308 K. X-ray quality crystals were formed on slow evaporation of methanol. (m.p.: 468- 475K).
All of the H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.95Å (CH); 0.99Å (CH2); 0.84Å (OH) or 0.91Å (NH3) . Isotropic displacement parameters for these atoms were set to 1.2 (CH, CH2, NH3) or 1.5 (OH) times Ueq of the parent atom. Idealised ammonium and tetrahedral OH were refined as rotating groups.
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).Fig. 1. ORTEP drawing of (I) ( C6H12N3+.C7H3N2O7-) showing the labeling scheme with 30% probability displacement ellipsoids. Dashed lines indicate a O2B—H2B···O1B intramolecular hydrogen bond in the anion within the asymmetric unit. | |
Fig. 2. Molecular packing for (I) viewed along the a axis. Dashed lines indicate N—H···O, N—H···N intermolecular hydrogen bonds and weak C—H···O intermolecular interactions. H atoms not involved in hydrogen bonding have been removed for clarity. |
C6H12N3+·C7H3N2O7− | Z = 2 |
Mr = 353.30 | F(000) = 368 |
Triclinic, P1 | Dx = 1.525 Mg m−3 |
a = 7.0109 (4) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 10.6617 (8) Å | Cell parameters from 2218 reflections |
c = 10.7454 (7) Å | θ = 4.2–72.3° |
α = 93.075 (6)° | µ = 1.09 mm−1 |
β = 95.863 (5)° | T = 173 K |
γ = 104.944 (6)° | Irregular, yellow |
V = 769.30 (9) Å3 | 0.22 × 0.14 × 0.12 mm |
Agilent Xcalibur (Eos, Gemini) diffractometer | 2953 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 2582 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 72.5°, θmin = 4.2° |
ω scans | h = −8→5 |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | k = −12→13 |
Tmin = 0.925, Tmax = 1.000 | l = −13→13 |
4664 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0682P)2 + 0.1101P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.122 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.25 e Å−3 |
2953 reflections | Δρmin = −0.25 e Å−3 |
229 parameters | Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0087 (12) |
Primary atom site location: structure-invariant direct methods |
C6H12N3+·C7H3N2O7− | γ = 104.944 (6)° |
Mr = 353.30 | V = 769.30 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.0109 (4) Å | Cu Kα radiation |
b = 10.6617 (8) Å | µ = 1.09 mm−1 |
c = 10.7454 (7) Å | T = 173 K |
α = 93.075 (6)° | 0.22 × 0.14 × 0.12 mm |
β = 95.863 (5)° |
Agilent Xcalibur (Eos, Gemini) diffractometer | 2953 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | 2582 reflections with I > 2σ(I) |
Tmin = 0.925, Tmax = 1.000 | Rint = 0.026 |
4664 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.25 e Å−3 |
2953 reflections | Δρmin = −0.25 e Å−3 |
229 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1B | −0.19166 (16) | 0.67530 (11) | 0.52669 (10) | 0.0288 (3) | |
O2B | −0.38294 (16) | 0.47146 (11) | 0.40815 (11) | 0.0309 (3) | |
H2B | −0.3493 | 0.5402 | 0.4563 | 0.046* | |
O3B | −0.25490 (16) | 0.37708 (11) | 0.26154 (11) | 0.0308 (3) | |
O4B | 0.41267 (18) | 0.58644 (12) | 0.16868 (12) | 0.0360 (3) | |
O5B | 0.59770 (17) | 0.75622 (12) | 0.28233 (13) | 0.0378 (3) | |
O6B | 0.34447 (19) | 0.93705 (13) | 0.62652 (14) | 0.0466 (4) | |
O7B | 0.02866 (19) | 0.91669 (12) | 0.61489 (13) | 0.0407 (3) | |
N1B | 0.1720 (2) | 0.88464 (13) | 0.58134 (13) | 0.0293 (3) | |
N2B | 0.43937 (19) | 0.67328 (13) | 0.25380 (13) | 0.0277 (3) | |
C1B | −0.0459 (2) | 0.68012 (14) | 0.46271 (13) | 0.0220 (3) | |
C2B | −0.0571 (2) | 0.57869 (14) | 0.36592 (13) | 0.0216 (3) | |
C3B | 0.0986 (2) | 0.57928 (14) | 0.29803 (13) | 0.0224 (3) | |
H3B | 0.0860 | 0.5126 | 0.2331 | 0.027* | |
C4B | 0.2742 (2) | 0.67709 (15) | 0.32417 (14) | 0.0235 (3) | |
C5B | 0.2969 (2) | 0.77675 (14) | 0.41652 (14) | 0.0242 (3) | |
H5B | 0.4187 | 0.8428 | 0.4339 | 0.029* | |
C6B | 0.1396 (2) | 0.77858 (15) | 0.48287 (14) | 0.0240 (3) | |
C7B | −0.2410 (2) | 0.46764 (15) | 0.34003 (14) | 0.0240 (3) | |
N1A | −0.2236 (2) | 0.05132 (13) | −0.17302 (13) | 0.0301 (3) | |
N2A | −0.01482 (18) | 0.22563 (12) | −0.06974 (12) | 0.0236 (3) | |
N3A | 0.34673 (18) | 0.20535 (12) | 0.28180 (12) | 0.0247 (3) | |
H3AA | 0.3273 | 0.1193 | 0.2584 | 0.030* | |
H3AB | 0.3097 | 0.2146 | 0.3598 | 0.030* | |
H3AC | 0.4776 | 0.2474 | 0.2829 | 0.030* | |
C1A | −0.0393 (2) | 0.12597 (15) | −0.15759 (15) | 0.0267 (3) | |
H1A | 0.0635 | 0.1112 | −0.2029 | 0.032* | |
C2A | −0.3211 (2) | 0.10673 (16) | −0.08994 (16) | 0.0311 (4) | |
H2A | −0.4575 | 0.0745 | −0.0793 | 0.037* | |
C3A | −0.1954 (2) | 0.21366 (16) | −0.02562 (15) | 0.0290 (4) | |
H3A | −0.2257 | 0.2692 | 0.0372 | 0.035* | |
C4A | 0.1721 (2) | 0.32486 (15) | −0.02842 (14) | 0.0265 (3) | |
H4AA | 0.1419 | 0.4032 | 0.0094 | 0.032* | |
H4AB | 0.2423 | 0.3502 | −0.1023 | 0.032* | |
C5A | 0.3076 (2) | 0.27761 (16) | 0.06655 (14) | 0.0270 (3) | |
H5AA | 0.3236 | 0.1929 | 0.0335 | 0.032* | |
H5AB | 0.4405 | 0.3407 | 0.0792 | 0.032* | |
C6A | 0.2253 (2) | 0.26209 (16) | 0.19094 (14) | 0.0276 (3) | |
H6AA | 0.2200 | 0.3483 | 0.2271 | 0.033* | |
H6AB | 0.0877 | 0.2051 | 0.1769 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1B | 0.0263 (6) | 0.0300 (6) | 0.0273 (6) | 0.0012 (5) | 0.0097 (4) | −0.0047 (4) |
O2B | 0.0247 (6) | 0.0304 (6) | 0.0321 (6) | −0.0027 (4) | 0.0082 (5) | −0.0070 (5) |
O3B | 0.0276 (6) | 0.0282 (6) | 0.0318 (6) | 0.0003 (5) | 0.0045 (5) | −0.0081 (5) |
O4B | 0.0360 (6) | 0.0319 (6) | 0.0414 (7) | 0.0081 (5) | 0.0168 (5) | −0.0040 (5) |
O5B | 0.0229 (6) | 0.0376 (7) | 0.0501 (8) | 0.0011 (5) | 0.0111 (5) | 0.0012 (6) |
O6B | 0.0351 (7) | 0.0402 (8) | 0.0540 (8) | −0.0004 (6) | −0.0049 (6) | −0.0192 (6) |
O7B | 0.0393 (7) | 0.0324 (7) | 0.0472 (8) | 0.0026 (5) | 0.0160 (6) | −0.0121 (6) |
N1B | 0.0319 (7) | 0.0233 (7) | 0.0293 (7) | 0.0012 (5) | 0.0057 (6) | −0.0025 (5) |
N2B | 0.0253 (7) | 0.0258 (7) | 0.0339 (7) | 0.0072 (5) | 0.0088 (5) | 0.0060 (5) |
C1B | 0.0230 (7) | 0.0232 (7) | 0.0194 (7) | 0.0049 (6) | 0.0033 (5) | 0.0023 (6) |
C2B | 0.0215 (7) | 0.0215 (7) | 0.0207 (7) | 0.0035 (6) | 0.0021 (5) | 0.0028 (6) |
C3B | 0.0255 (7) | 0.0216 (7) | 0.0210 (7) | 0.0072 (6) | 0.0043 (6) | 0.0016 (5) |
C4B | 0.0220 (7) | 0.0248 (7) | 0.0258 (7) | 0.0076 (6) | 0.0066 (6) | 0.0059 (6) |
C5B | 0.0215 (7) | 0.0221 (7) | 0.0268 (7) | 0.0017 (6) | 0.0023 (6) | 0.0051 (6) |
C6B | 0.0270 (8) | 0.0208 (7) | 0.0226 (7) | 0.0041 (6) | 0.0017 (6) | 0.0002 (6) |
C7B | 0.0240 (7) | 0.0253 (7) | 0.0213 (7) | 0.0047 (6) | 0.0016 (5) | 0.0001 (6) |
N1A | 0.0291 (7) | 0.0246 (7) | 0.0347 (7) | 0.0050 (5) | 0.0016 (6) | −0.0005 (6) |
N2A | 0.0241 (6) | 0.0230 (6) | 0.0229 (6) | 0.0049 (5) | 0.0032 (5) | 0.0002 (5) |
N3A | 0.0258 (6) | 0.0224 (6) | 0.0241 (6) | 0.0041 (5) | 0.0025 (5) | −0.0028 (5) |
C1A | 0.0273 (8) | 0.0256 (8) | 0.0277 (8) | 0.0078 (6) | 0.0050 (6) | −0.0019 (6) |
C2A | 0.0262 (8) | 0.0311 (8) | 0.0354 (9) | 0.0045 (6) | 0.0070 (6) | 0.0059 (7) |
C3A | 0.0293 (8) | 0.0308 (8) | 0.0286 (8) | 0.0093 (6) | 0.0093 (6) | 0.0013 (6) |
C4A | 0.0268 (8) | 0.0245 (7) | 0.0248 (7) | 0.0007 (6) | 0.0048 (6) | −0.0001 (6) |
C5A | 0.0237 (7) | 0.0293 (8) | 0.0258 (8) | 0.0029 (6) | 0.0054 (6) | −0.0020 (6) |
C6A | 0.0301 (8) | 0.0301 (8) | 0.0256 (8) | 0.0124 (6) | 0.0060 (6) | 0.0017 (6) |
O1B—C1B | 1.2803 (18) | N1A—C2A | 1.375 (2) |
O2B—H2B | 0.8400 | N2A—C1A | 1.3472 (19) |
O2B—C7B | 1.3019 (18) | N2A—C3A | 1.3748 (19) |
O3B—C7B | 1.2249 (18) | N2A—C4A | 1.4660 (19) |
O4B—N2B | 1.2303 (18) | N3A—H3AA | 0.9100 |
O5B—N2B | 1.2261 (18) | N3A—H3AB | 0.9100 |
O6B—N1B | 1.2300 (18) | N3A—H3AC | 0.9100 |
O7B—N1B | 1.2224 (18) | N3A—C6A | 1.4844 (19) |
N1B—C6B | 1.4629 (19) | C1A—H1A | 0.9500 |
N2B—C4B | 1.4540 (18) | C2A—H2A | 0.9500 |
C1B—C2B | 1.441 (2) | C2A—C3A | 1.352 (2) |
C1B—C6B | 1.433 (2) | C3A—H3A | 0.9500 |
C2B—C3B | 1.373 (2) | C4A—H4AA | 0.9900 |
C2B—C7B | 1.498 (2) | C4A—H4AB | 0.9900 |
C3B—H3B | 0.9500 | C4A—C5A | 1.517 (2) |
C3B—C4B | 1.385 (2) | C5A—H5AA | 0.9900 |
C4B—C5B | 1.381 (2) | C5A—H5AB | 0.9900 |
C5B—H5B | 0.9500 | C5A—C6A | 1.510 (2) |
C5B—C6B | 1.377 (2) | C6A—H6AA | 0.9900 |
N1A—C1A | 1.320 (2) | C6A—H6AB | 0.9900 |
C7B—O2B—H2B | 109.5 | H3AA—N3A—H3AC | 109.5 |
O6B—N1B—C6B | 117.54 (13) | H3AB—N3A—H3AC | 109.5 |
O7B—N1B—O6B | 123.30 (14) | C6A—N3A—H3AA | 109.5 |
O7B—N1B—C6B | 119.17 (13) | C6A—N3A—H3AB | 109.5 |
O4B—N2B—C4B | 118.05 (13) | C6A—N3A—H3AC | 109.5 |
O5B—N2B—O4B | 123.43 (13) | N1A—C1A—N2A | 111.69 (13) |
O5B—N2B—C4B | 118.52 (13) | N1A—C1A—H1A | 124.2 |
O1B—C1B—C2B | 120.31 (13) | N2A—C1A—H1A | 124.2 |
O1B—C1B—C6B | 124.78 (14) | N1A—C2A—H2A | 124.8 |
C6B—C1B—C2B | 114.84 (13) | C3A—C2A—N1A | 110.33 (14) |
C1B—C2B—C7B | 119.59 (13) | C3A—C2A—H2A | 124.8 |
C3B—C2B—C1B | 121.69 (14) | N2A—C3A—H3A | 127.0 |
C3B—C2B—C7B | 118.70 (13) | C2A—C3A—N2A | 105.94 (14) |
C2B—C3B—H3B | 120.0 | C2A—C3A—H3A | 127.0 |
C2B—C3B—C4B | 120.03 (14) | N2A—C4A—H4AA | 109.1 |
C4B—C3B—H3B | 120.0 | N2A—C4A—H4AB | 109.1 |
C3B—C4B—N2B | 119.02 (13) | N2A—C4A—C5A | 112.48 (12) |
C5B—C4B—N2B | 119.37 (13) | H4AA—C4A—H4AB | 107.8 |
C5B—C4B—C3B | 121.60 (13) | C5A—C4A—H4AA | 109.1 |
C4B—C5B—H5B | 120.7 | C5A—C4A—H4AB | 109.1 |
C6B—C5B—C4B | 118.69 (14) | C4A—C5A—H5AA | 109.3 |
C6B—C5B—H5B | 120.7 | C4A—C5A—H5AB | 109.3 |
C1B—C6B—N1B | 120.14 (13) | H5AA—C5A—H5AB | 108.0 |
C5B—C6B—N1B | 116.69 (13) | C6A—C5A—C4A | 111.50 (12) |
C5B—C6B—C1B | 123.12 (14) | C6A—C5A—H5AA | 109.3 |
O2B—C7B—C2B | 116.03 (13) | C6A—C5A—H5AB | 109.3 |
O3B—C7B—O2B | 121.99 (14) | N3A—C6A—C5A | 112.37 (12) |
O3B—C7B—C2B | 121.96 (13) | N3A—C6A—H6AA | 109.1 |
C1A—N1A—C2A | 105.07 (13) | N3A—C6A—H6AB | 109.1 |
C1A—N2A—C3A | 106.97 (13) | C5A—C6A—H6AA | 109.1 |
C1A—N2A—C4A | 125.58 (13) | C5A—C6A—H6AB | 109.1 |
C3A—N2A—C4A | 127.43 (13) | H6AA—C6A—H6AB | 107.9 |
H3AA—N3A—H3AB | 109.5 | ||
O1B—C1B—C2B—C3B | −178.23 (13) | C3B—C2B—C7B—O2B | 179.26 (13) |
O1B—C1B—C2B—C7B | 0.3 (2) | C3B—C2B—C7B—O3B | 1.0 (2) |
O1B—C1B—C6B—N1B | −0.9 (2) | C3B—C4B—C5B—C6B | −0.6 (2) |
O1B—C1B—C6B—C5B | 176.43 (14) | C4B—C5B—C6B—N1B | 178.87 (13) |
O4B—N2B—C4B—C3B | 3.8 (2) | C4B—C5B—C6B—C1B | 1.5 (2) |
O4B—N2B—C4B—C5B | −177.14 (13) | C6B—C1B—C2B—C3B | −0.9 (2) |
O5B—N2B—C4B—C3B | −176.02 (14) | C6B—C1B—C2B—C7B | 177.58 (12) |
O5B—N2B—C4B—C5B | 3.0 (2) | C7B—C2B—C3B—C4B | −176.73 (13) |
O6B—N1B—C6B—C1B | 154.04 (15) | N1A—C2A—C3A—N2A | 0.13 (18) |
O6B—N1B—C6B—C5B | −23.4 (2) | N2A—C4A—C5A—C6A | −69.71 (16) |
O7B—N1B—C6B—C1B | −25.8 (2) | C1A—N1A—C2A—C3A | 0.02 (18) |
O7B—N1B—C6B—C5B | 156.73 (14) | C1A—N2A—C3A—C2A | −0.23 (17) |
N2B—C4B—C5B—C6B | −179.60 (13) | C1A—N2A—C4A—C5A | −80.85 (18) |
C1B—C2B—C3B—C4B | 1.8 (2) | C2A—N1A—C1A—N2A | −0.17 (18) |
C1B—C2B—C7B—O2B | 0.7 (2) | C3A—N2A—C1A—N1A | 0.26 (18) |
C1B—C2B—C7B—O3B | −177.60 (13) | C3A—N2A—C4A—C5A | 97.42 (17) |
C2B—C1B—C6B—N1B | −178.03 (12) | C4A—N2A—C1A—N1A | 178.83 (13) |
C2B—C1B—C6B—C5B | −0.7 (2) | C4A—N2A—C3A—C2A | −178.77 (14) |
C2B—C3B—C4B—N2B | 177.99 (13) | C4A—C5A—C6A—N3A | 175.16 (12) |
C2B—C3B—C4B—C5B | −1.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2B—H2B···O1B | 0.84 | 1.66 | 2.4484 (15) | 155 |
N3A—H3AA···N1Ai | 0.91 | 1.92 | 2.7987 (19) | 162 |
N3A—H3AB···O1Bii | 0.91 | 2.03 | 2.8153 (17) | 144 |
N3A—H3AC···O3Biii | 0.91 | 2.07 | 2.9546 (17) | 165 |
C4A—H4AB···O4Biv | 0.99 | 2.53 | 3.3572 (19) | 142 |
Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2B—H2B···O1B | 0.84 | 1.66 | 2.4484 (15) | 155.0 |
N3A—H3AA···N1Ai | 0.91 | 1.92 | 2.7987 (19) | 162 |
N3A—H3AB···O1Bii | 0.91 | 2.03 | 2.8153 (17) | 144 |
N3A—H3AC···O3Biii | 0.91 | 2.07 | 2.9546 (17) | 165 |
C4A—H4AB···O4Biv | 0.99 | 2.53 | 3.3572 (19) | 142 |
Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+1, −y+1, −z. |
Acknowledgements
TSY thanks the University of Mysore for research facilities and is also grateful to the Principal, Maharani's Science College for Women, Mysore, for giving permission to undertake research. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.
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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.
Imidazole rings appear frequently in biologically active compounds, both natural and man-made (ten Have et al., 1997). Compounds with an imidazole ring system have many pharmacological properties and play important roles in biochemical processes (Lombardino & Wiseman, 1974). Most of the imidazole compounds are known as inhibitors of fungicides and herbicides, plant growth regulators and therapeutic agents (Maier et al., 1989), anticancer agents (Krezel, 1998) and bactericidal effects (Jackson et al., 2000). The crystal structures of some related compounds, viz ; 2-amino-5-methylpyridinium 2-hydroxy-3,5-dinitrobenzoate (Hemamalini et al., 2010); Cinnarizinium 3,5-dinitrosalicylate (Dayananda et al., 2012); Enrofloxacinium picrate (Jasinski et al., 2011); 3-(1H-imidazol-1-yl)propanaminium picrate (Yamuna et al., 2013); 3,5-dimethylpyrazolium 3,5-dinitrosalicylate (Wei et al., 2012), have been reported. In view of the importance of substituted imidazoles and organic acid–base adducts based on hydrogen bonding and receiving great attention in recent years, this paper reports the crystal structure of the title salt, (I), C6H12N3+.C7H3N2O7-.
The title salt, (I), C6H12N3+.C7H3N2O7-, crystallizes with one independent monocation (A) and monoanion (B) in the asymmetric unit (Fig. 1). In the cation the protonated imidazol-1-ium ring is planar (maximum deviation = 0.0013 (14)Å for N2A). In the anion, a single O—H···O intramolecular hydrogen bond is observed. Bond lengths are in normal ranges. The mean planes of the nitro groups in the anion are twisted from the phenyl ring mean plane with maximun angles of 24.7 (9)° and 3.9 (6)°, respectively. The hydrogen atoms on the terminal N atom of the cation form N—H···N and N—H···O intermolecular hydrogen bonds resulting in an infinite 1D chain along [1 1 1]. In the crystal, in addition to the classical hydrogen bonds, weak C—H···O (Table 1) and Cg1—Cg2 π—π intermolecular interactions are observed with an intercentroid distance of 3.7125 (9)Å (symmetry operation -x,1-y,-z; Cg1 and Cg2 are the centroids of the C1B–C6B and N1A/C1A/N2A/C3A/C2A rings) which contribute to crystal packing stability (Fig. 2).