Imidazolium 3-nitro-benzoate.

In the title compound, C(3)H(5)N(2) (+)·C(7)H(4)NO(4) (-), the benzene ring forms a dihedral angle of 40.60 (5)° with the imidizolium ring. The nitro-benzoate anion is approximately planar: the benzene ring makes dihedral angles of 3.8 (3) and 3.2 (1)° with the nitro and carboxyl-ate groups, respectively. In the crystal structure, the cations and anions are linked by inter-molecular N-H⋯O hydrogen bonds, forming a zigzag chain along the b axis.

Related literature

For general background to the physical and biological properties of imidazoles, see: Bunnage & Owen (2008 ▶); Ganellin & Fkyerat (1996 ▶); Weinreb (2007 ▶). For related structures of salts of imidazole with carboxylic acid derivatives, see: Mcdonald & Dorrestein (2001 ▶).

Experimental

Crystal data

C3H5N2 +·C7H4NO4 −

M = 235.20

Monoclinic,

a = 12.209 (2) Å

b = 12.081 (2) Å

c = 7.3216 (15) Å

β = 106.38 (3)°

V = 1036.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 298 K

0.38 × 0.21 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer

Absorption correction: multi-scan (; Higashi, 1995 ▶) T min = 0.956, T max = 0.984

10057 measured reflections

2369 independent reflections

1571 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.108

S = 1.02

2369 reflections

163 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013142/is2403sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013142/is2403Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C3H5N2+·C7H4NO4−	F(000) = 488
Mr = 235.20	Dx = 1.508 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6213 reflections
a = 12.209 (2) Å	θ = 3.4–27.5°
b = 12.081 (2) Å	µ = 0.12 mm−1
c = 7.3216 (15) Å	T = 298 K
β = 106.38 (3)°	Block, colourless
V = 1036.1 (3) Å3	0.38 × 0.21 × 0.13 mm
Z = 4

Rigaku R-AXIS RAPID IP area-detector diffractometer	2369 independent reflections
Radiation source: rotating anode	1571 reflections with I > 2σ(I)
graphite	Rint = 0.051
ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −15→14
Tmin = 0.956, Tmax = 0.984	k = −15→15
10057 measured reflections	l = −9→9

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0443P)2 + 0.1735P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2369 reflections	Δρmax = 0.20 e Å−3
163 parameters	Δρmin = −0.17 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: 0.019 (3)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
C1	0.25763 (13)	0.52628 (15)	0.1825 (3)	0.0382 (4)
C2	0.35926 (13)	0.45955 (14)	0.1673 (2)	0.0337 (4)
C3	0.34637 (15)	0.36098 (15)	0.0674 (3)	0.0409 (4)
H3A	0.2733	0.3348	0.0082	0.049*
C4	0.44008 (17)	0.30055 (16)	0.0538 (3)	0.0470 (5)
H4A	0.4294	0.2345	−0.0142	0.056*
C5	0.54890 (16)	0.33750 (16)	0.1401 (3)	0.0463 (5)
H5A	0.6125	0.2971	0.1332	0.056*
C6	0.56048 (14)	0.43670 (15)	0.2374 (2)	0.0373 (4)
C7	0.46907 (13)	0.49843 (14)	0.2524 (2)	0.0352 (4)
H7A	0.4804	0.5652	0.3183	0.042*
C8	0.05956 (14)	0.80035 (16)	0.3479 (3)	0.0417 (4)
H8	0.1048	0.8624	0.3490	0.050*
C9	0.00096 (16)	0.63117 (17)	0.3339 (3)	0.0509 (5)
H9	−0.0009	0.5545	0.3227	0.061*
C10	−0.08242 (16)	0.69552 (17)	0.3607 (3)	0.0485 (5)
H10	−0.1528	0.6721	0.3719	0.058*
N1	0.67578 (12)	0.48134 (15)	0.3229 (2)	0.0460 (4)
H1	0.160 (2)	0.670 (2)	0.304 (3)	0.084 (8)*
H2	−0.0847 (18)	0.865 (2)	0.384 (3)	0.066 (6)*
N2	−0.04454 (13)	0.80152 (14)	0.3686 (2)	0.0432 (4)
N3	0.08885 (12)	0.69827 (13)	0.3259 (2)	0.0423 (4)
O1	0.16009 (9)	0.48714 (11)	0.1101 (2)	0.0507 (4)
O2	0.27753 (10)	0.61707 (11)	0.2665 (2)	0.0510 (4)
O3	0.68555 (10)	0.56865 (13)	0.4101 (2)	0.0574 (4)
O4	0.75732 (11)	0.42975 (14)	0.3012 (2)	0.0721 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0339 (8)	0.0330 (10)	0.0495 (11)	−0.0009 (7)	0.0148 (8)	0.0051 (8)
C2	0.0350 (8)	0.0296 (9)	0.0380 (9)	0.0006 (7)	0.0129 (7)	0.0043 (7)
C3	0.0442 (9)	0.0352 (10)	0.0444 (10)	−0.0038 (8)	0.0143 (8)	0.0009 (8)
C4	0.0624 (12)	0.0311 (10)	0.0527 (11)	0.0026 (8)	0.0246 (10)	−0.0023 (9)
C5	0.0506 (11)	0.0402 (11)	0.0548 (12)	0.0155 (8)	0.0256 (9)	0.0076 (9)
C6	0.0340 (8)	0.0392 (10)	0.0406 (10)	0.0064 (7)	0.0139 (7)	0.0082 (8)
C7	0.0363 (8)	0.0310 (9)	0.0411 (9)	0.0023 (7)	0.0157 (8)	0.0010 (7)
N1	0.0340 (8)	0.0561 (11)	0.0499 (10)	0.0087 (7)	0.0152 (7)	0.0108 (8)
O1	0.0309 (6)	0.0412 (8)	0.0769 (10)	−0.0044 (5)	0.0100 (6)	−0.0008 (7)
O2	0.0354 (6)	0.0370 (8)	0.0836 (10)	−0.0003 (5)	0.0215 (7)	−0.0128 (7)
O3	0.0398 (7)	0.0578 (10)	0.0742 (10)	−0.0063 (6)	0.0154 (7)	−0.0032 (8)
O4	0.0378 (7)	0.0952 (14)	0.0870 (12)	0.0218 (8)	0.0234 (8)	−0.0012 (10)
C8	0.0346 (9)	0.0400 (11)	0.0514 (11)	−0.0031 (7)	0.0137 (8)	−0.0015 (9)
C9	0.0518 (11)	0.0373 (11)	0.0667 (13)	−0.0075 (9)	0.0221 (10)	−0.0067 (10)
C10	0.0375 (9)	0.0534 (13)	0.0583 (12)	−0.0082 (8)	0.0194 (9)	−0.0060 (10)
N2	0.0373 (8)	0.0435 (10)	0.0500 (9)	0.0054 (7)	0.0144 (7)	−0.0031 (7)
N3	0.0352 (8)	0.0413 (9)	0.0523 (9)	0.0039 (7)	0.0153 (7)	−0.0048 (7)

C8—N3	1.307 (2)	C2—C3	1.383 (2)
C8—N2	1.322 (2)	C2—C7	1.391 (2)
C8—H8	0.9300	C3—C4	1.384 (3)
C9—C10	1.339 (3)	C3—H3A	0.9300
C9—N3	1.359 (2)	C4—C5	1.375 (3)
C9—H9	0.9300	C4—H4A	0.9300
C10—N2	1.357 (2)	C5—C6	1.381 (2)
C10—H10	0.9300	C5—H5A	0.9300
N2—H2	0.94 (2)	C6—C7	1.372 (2)
N3—H1	0.99 (2)	C6—N1	1.472 (2)
C1—O2	1.247 (2)	C7—H7A	0.9300
C1—O1	1.252 (2)	N1—O3	1.221 (2)
C1—C2	1.510 (2)	N1—O4	1.2223 (19)
N3—C8—N2	109.25 (16)	C7—C2—C1	119.68 (15)
N3—C8—H8	125.4	C2—C3—C4	121.27 (17)
N2—C8—H8	125.4	C2—C3—H3A	119.4
C10—C9—N3	107.59 (17)	C4—C3—H3A	119.4
C10—C9—H9	126.2	C5—C4—C3	120.45 (18)
N3—C9—H9	126.2	C5—C4—H4A	119.8
C9—C10—N2	106.85 (16)	C3—C4—H4A	119.8
C9—C10—H10	126.6	C4—C5—C6	117.64 (16)
N2—C10—H10	126.6	C4—C5—H5A	121.2
C8—N2—C10	108.20 (16)	C6—C5—H5A	121.2
C8—N2—H2	125.1 (14)	C7—C6—C5	123.07 (17)
C10—N2—H2	126.7 (14)	C7—C6—N1	117.95 (16)
C8—N3—C9	108.11 (15)	C5—C6—N1	118.93 (15)
C8—N3—H1	128.8 (14)	C6—C7—C2	118.93 (16)
C9—N3—H1	123.1 (14)	C6—C7—H7A	120.5
O2—C1—O1	124.82 (16)	C2—C7—H7A	120.5
O2—C1—C2	117.12 (14)	O3—N1—O4	123.05 (17)
O1—C1—C2	118.06 (16)	O3—N1—C6	118.65 (14)
C3—C2—C7	118.62 (15)	O4—N1—C6	118.29 (17)
C3—C2—C1	121.69 (15)
N3—C9—C10—N2	0.1 (2)	C3—C4—C5—C6	−0.8 (3)
N3—C8—N2—C10	0.5 (2)	C4—C5—C6—C7	0.5 (3)
C9—C10—N2—C8	−0.4 (2)	C4—C5—C6—N1	−176.88 (16)
N2—C8—N3—C9	−0.4 (2)	C5—C6—C7—C2	0.5 (3)
C10—C9—N3—C8	0.2 (2)	N1—C6—C7—C2	177.96 (14)
O2—C1—C2—C3	−176.11 (16)	C3—C2—C7—C6	−1.3 (2)
O1—C1—C2—C3	3.7 (3)	C1—C2—C7—C6	179.92 (15)
O2—C1—C2—C7	2.6 (2)	C7—C6—N1—O3	3.0 (2)
O1—C1—C2—C7	−177.59 (16)	C5—C6—N1—O3	−179.45 (16)
C7—C2—C3—C4	1.0 (3)	C7—C6—N1—O4	−176.07 (16)
C1—C2—C3—C4	179.79 (16)	C5—C6—N1—O4	1.5 (2)
C2—C3—C4—C5	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O2	0.99 (2)	1.66 (2)	2.6502 (18)	177 (2)
N2—H2···O1i	0.94 (2)	1.74 (2)	2.677 (2)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O2	0.99 (2)	1.66 (2)	2.6502 (18)	177 (2)
N2—H2⋯O1i	0.94 (2)	1.74 (2)	2.677 (2)	175 (2)

Symmetry code: (i) .