Imidazolium 4-amino-benzoate.

In the title salt, C(3)H(5)N(2) (+)·C(7)H(6)NO(2) (-), the carboxyl-ate group of the 4-amino-benzoate anion forms a dihedral angle of 13.23 (17)° with respect to the benzene ring. There are N-H⋯O hydrogen-bonding inter-actions between the anion and cation, and weak inter-molecular C-H⋯O contacts with carboxyl-ate O-atom acceptors of the 4-amino-benzoate anion result in extended three-dimensional R(4) (4)(22) and R(5) (6)(30) edge-fused rings along the [100], [010] and [001] directions.

Related literature

For the anti­microbial and anti­protozoal biological activity of imidazole, see: Kopanska et al. (2004 ▶); Sondhi et al. (2002 ▶). For the biological activity of 4-amino­benzoic acid, see: Lai & Marsh (1967 ▶); Robinson (1966 ▶). For related structures, see: Moreno-Fuquen et al. (1996 ▶, 2009 ▶); McMullan et al. (1979 ▶). For hydrogen-bond motifs, see: Etter (1990 ▶). For hydrogen bonds, see: Nardelli (1995 ▶).

Experimental

Crystal data

C3H5N2 +·C7H6NO2 −

M = 205.22

Monoclinic,

a = 7.2038 (5) Å

b = 11.6812 (6) Å

c = 12.0152 (6) Å

β = 105.223 (6)°

V = 975.59 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 123 K

0.20 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction Gemini S diffractometer

Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2009 ▶) T min = 0.945, T max = 1.000

8533 measured reflections

2360 independent reflections

1700 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.115

S = 1.02

2360 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680904625X/fj2253sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904625X/fj2253Isup2.hkl

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

C3H5N2+·C7H6NO2−	F(000) = 432
Mr = 205.22	Dx = 1.397 Mg m−3
Monoclinic, P21/n	Melting point: 443.0(10) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.2038 (5) Å	Cell parameters from 3056 reflections
b = 11.6812 (6) Å	θ = 2.5–30.9°
c = 12.0152 (6) Å	µ = 0.10 mm−1
β = 105.223 (6)°	T = 123 K
V = 975.59 (10) Å3	Fragment, colourless
Z = 4	0.20 × 0.15 × 0.12 mm

Oxford Diffraction Gemini S diffractometer	2360 independent reflections
Radiation source: fine-focus sealed tube	1700 reflections with I > 2σ(I)
graphite	Rint = 0.049
ω scans	θmax = 28.0°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2009)	h = −9→9
Tmin = 0.945, Tmax = 1.000	k = −13→15
8533 measured reflections	l = −15→15

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.067P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2360 reflections	Δρmax = 0.28 e Å−3
153 parameters	Δρmin = −0.36 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: 0.213 (14)

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
O1	0.13700 (14)	0.80374 (8)	0.58020 (7)	0.0227 (3)
O2	0.27846 (15)	0.96304 (8)	0.54056 (8)	0.0243 (3)
N1	0.2159 (2)	0.68622 (11)	0.07332 (10)	0.0247 (3)
N2	0.77001 (18)	0.91059 (11)	0.13156 (10)	0.0246 (3)
N3	0.84977 (17)	1.06234 (10)	0.23605 (10)	0.0231 (3)
C1	0.2104 (2)	0.86668 (12)	0.51343 (11)	0.0201 (3)
C2	0.21134 (19)	0.81695 (11)	0.39852 (10)	0.0187 (3)
C3	0.3206 (2)	0.86798 (12)	0.33249 (11)	0.0218 (3)
H3	0.3954	0.9338	0.3613	0.026*
C4	0.3225 (2)	0.82474 (12)	0.22568 (11)	0.0222 (3)
H4	0.3975	0.8615	0.1819	0.027*
C5	0.2148 (2)	0.72728 (12)	0.18135 (11)	0.0206 (3)
C6	0.1034 (2)	0.67656 (11)	0.24708 (11)	0.0212 (3)
H6	0.0274	0.6112	0.2181	0.025*
C7	0.10240 (19)	0.72053 (11)	0.35398 (11)	0.0204 (3)
H7	0.0265	0.6845	0.3977	0.025*
C8	0.7922 (2)	0.95506 (12)	0.23596 (12)	0.0238 (3)
H8	0.7701	0.9158	0.3005	0.029*
C9	0.8142 (2)	0.99372 (12)	0.06171 (12)	0.0268 (4)
H9	0.8099	0.9859	−0.0176	0.032*
C10	0.8650 (2)	1.08847 (13)	0.12684 (12)	0.0266 (4)
H10	0.9039	1.1597	0.1021	0.032*
H1N	0.175 (3)	0.6098 (17)	0.0598 (16)	0.048 (5)*
H2N	0.323 (3)	0.7036 (15)	0.0534 (16)	0.044 (5)*
H3N	0.729 (3)	0.8341 (16)	0.1097 (16)	0.045 (5)*
H4N	0.860 (3)	1.1143 (18)	0.2961 (19)	0.060 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0297 (6)	0.0203 (5)	0.0205 (5)	−0.0014 (4)	0.0109 (4)	0.0007 (4)
O2	0.0344 (6)	0.0186 (5)	0.0202 (5)	−0.0044 (4)	0.0076 (4)	−0.0017 (4)
N1	0.0300 (8)	0.0252 (7)	0.0200 (6)	−0.0044 (6)	0.0085 (5)	−0.0036 (5)
N2	0.0290 (7)	0.0209 (6)	0.0257 (6)	−0.0012 (5)	0.0103 (5)	−0.0042 (5)
N3	0.0257 (7)	0.0216 (6)	0.0233 (6)	−0.0008 (5)	0.0083 (5)	−0.0044 (5)
C1	0.0210 (7)	0.0198 (7)	0.0188 (6)	0.0031 (6)	0.0041 (5)	0.0016 (5)
C2	0.0213 (7)	0.0176 (7)	0.0167 (6)	0.0013 (5)	0.0042 (5)	0.0011 (5)
C3	0.0252 (8)	0.0194 (7)	0.0209 (6)	−0.0029 (6)	0.0063 (6)	−0.0002 (5)
C4	0.0260 (8)	0.0225 (7)	0.0199 (6)	−0.0033 (6)	0.0095 (5)	0.0018 (5)
C5	0.0215 (7)	0.0214 (7)	0.0178 (6)	0.0029 (6)	0.0033 (5)	0.0004 (5)
C6	0.0216 (7)	0.0186 (7)	0.0222 (6)	−0.0026 (6)	0.0038 (5)	−0.0010 (5)
C7	0.0208 (7)	0.0197 (7)	0.0215 (7)	−0.0009 (6)	0.0066 (5)	0.0021 (5)
C8	0.0272 (8)	0.0217 (7)	0.0231 (7)	0.0020 (6)	0.0076 (6)	−0.0020 (5)
C9	0.0305 (8)	0.0281 (8)	0.0247 (7)	−0.0031 (6)	0.0122 (6)	−0.0021 (6)
C10	0.0308 (8)	0.0244 (8)	0.0269 (7)	−0.0005 (6)	0.0118 (6)	0.0021 (6)

O1—C1	1.2987 (16)	C2—C7	1.3964 (18)
O2—C1	1.2368 (16)	C3—C4	1.3825 (18)
N1—C5	1.3858 (17)	C3—H3	0.9500
N1—H1N	0.94 (2)	C4—C5	1.4016 (19)
N1—H2N	0.89 (2)	C4—H4	0.9500
N2—C8	1.3281 (17)	C5—C6	1.397 (2)
N2—C9	1.3745 (19)	C6—C7	1.3850 (18)
N2—H3N	0.956 (19)	C6—H6	0.9500
N3—C8	1.3200 (19)	C7—H7	0.9500
N3—C10	1.3794 (18)	C8—H8	0.9500
N3—H4N	0.93 (2)	C9—C10	1.349 (2)
C1—C2	1.4996 (18)	C9—H9	0.9500
C2—C3	1.3900 (19)	C10—H10	0.9500
C5—N1—H1N	114.3 (12)	C5—C4—H4	119.7
C5—N1—H2N	113.1 (12)	N1—C5—C6	121.89 (13)
H1N—N1—H2N	115.1 (18)	N1—C5—C4	119.88 (13)
C8—N2—C9	108.10 (12)	C6—C5—C4	118.19 (12)
C8—N2—H3N	125.2 (12)	C7—C6—C5	120.69 (12)
C9—N2—H3N	126.6 (12)	C7—C6—H6	119.7
C8—N3—C10	108.23 (12)	C5—C6—H6	119.7
C8—N3—H4N	125.5 (13)	C6—C7—C2	121.02 (13)
C10—N3—H4N	125.7 (13)	C6—C7—H7	119.5
O2—C1—O1	123.37 (12)	C2—C7—H7	119.5
O2—C1—C2	119.86 (12)	N3—C8—N2	109.39 (13)
O1—C1—C2	116.77 (12)	N3—C8—H8	125.3
C3—C2—C7	118.20 (12)	N2—C8—H8	125.3
C3—C2—C1	119.96 (12)	C10—C9—N2	107.24 (13)
C7—C2—C1	121.83 (12)	C10—C9—H9	126.4
C4—C3—C2	121.20 (13)	N2—C9—H9	126.4
C4—C3—H3	119.4	C9—C10—N3	107.04 (13)
C2—C3—H3	119.4	C9—C10—H10	126.5
C3—C4—C5	120.68 (13)	N3—C10—H10	126.5
C3—C4—H4	119.7
O2—C1—C2—C3	12.6 (2)	C4—C5—C6—C7	−1.1 (2)
O1—C1—C2—C3	−167.05 (12)	C5—C6—C7—C2	0.5 (2)
O2—C1—C2—C7	−166.47 (12)	C3—C2—C7—C6	0.2 (2)
O1—C1—C2—C7	13.89 (18)	C1—C2—C7—C6	179.26 (12)
C7—C2—C3—C4	−0.2 (2)	C10—N3—C8—N2	0.15 (16)
C1—C2—C3—C4	−179.26 (12)	C9—N2—C8—N3	−0.43 (16)
C2—C3—C4—C5	−0.5 (2)	C8—N2—C9—C10	0.55 (17)
C3—C4—C5—N1	178.96 (13)	N2—C9—C10—N3	−0.45 (17)
C3—C4—C5—C6	1.1 (2)	C8—N3—C10—C9	0.19 (16)
N1—C5—C6—C7	−178.90 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H4N···O1i	0.93 (2)	1.76 (2)	2.6869 (15)	171 (2)
N2—H3N···O1ii	0.956 (19)	1.742 (19)	2.6938 (15)	173.5 (19)
N1—H1N···O2iii	0.94 (2)	2.17 (2)	2.9495 (16)	139.3 (17)
N1—H2N···O1ii	0.89 (2)	2.20 (2)	3.0149 (17)	152.0 (16)
C6—H6···O2iv	0.95	2.55	3.3533 (16)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H4N⋯O1i	0.93 (2)	1.76 (2)	2.6869 (15)	171 (2)
N2—H3N⋯O1ii	0.956 (19)	1.742 (19)	2.6938 (15)	173.5 (19)
N1—H1N⋯O2iii	0.94 (2)	2.17 (2)	2.9495 (16)	139.3 (17)
N1—H2N⋯O1ii	0.89 (2)	2.20 (2)	3.0149 (17)	152.0 (16)
C6—H6⋯O2iv	0.95	2.55	3.3533 (16)	142

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