3-(1H-Imidazol-1-yl)propanaminium 2-carb-oxy-4,6-di-nitro-phenolate.

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 intra-molecular 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] inter-actions are also observed, which lead to the formation a three-dimensional supramolecular structure that links the chains into layers along the bc plane.

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

C6H12N3 +·C7H3N2O7 −

M = 353.30

Triclinic,

a = 7.0109 (4) Å

b = 10.6617 (8) Å

c = 10.7454 (7) Å

α = 93.075 (6)°

β = 95.863 (5)°

γ = 104.944 (6)°

V = 769.30 (9) Å3

Z = 2

Cu Kα radiation

μ = 1.09 mm−1

T = 173 K

0.22 × 0.14 × 0.12 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.925, T max = 1.000

4664 measured reflections

2953 independent reflections

2582 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.122

S = 1.04

2953 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: 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.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814003146/fj2659sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003146/fj2659Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003146/fj2659Isup3.cml

CCDC reference: 986378

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

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

Table 1

Hydrogen-bond geometry (Å, °)

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⋯N1A i	0.91	1.92	2.7987 (19)	162
N3A—H3AB⋯O1B ii	0.91	2.03	2.8153 (17)	144
N3A—H3AC⋯O3B iii	0.91	2.07	2.9546 (17)	165
C4A—H4AB⋯O4B iv	0.99	2.53	3.3572 (19)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .