3-Nitro-5-(4-pyridinio)benzoate.

The title compound, C(12)H(8)N(2)O(4), crystallizes as a zwitterion in which the pyridyl N atom is protonated. The dihedral angle between the benzene and pyridinium rings is 27.9 (2)°. In the crystal, N-H⋯O hydrogen bonds link adjacent zwitterions into a three-dimensional structure.

Related literature

The title compound was reacted with MgCl2 under hydrothermal conditions in an attempt to obtain a new coordination polymer as part of our investigation of pyridine caboxylate coordination polymers. For the advantages of hydro­thermal synthesis, see: Feng et al. (2001 ▶); Tao et al. (2001 ▶). For the crystal structures of coord­in­ation polymers involving 4-pyridine­carboxyl­ate ligands, see: Lu et al. (2003 ▶).

Experimental

Crystal data

C12H8N2O4

M = 244.20

Orthorhombic,

a = 16.1215 (14) Å

b = 37.126 (3) Å

c = 7.1317 (8) Å

V = 4268.5 (7) Å3

Z = 16

Mo Kα radiation

μ = 0.12 mm−1

T = 298 K

0.46 × 0.17 × 0.09 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.948, T max = 0.990

4377 measured reflections

1023 independent reflections

621 reflections with I > 2σ(I)

R int = 0.110

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.118

S = 1.02

1023 reflections

163 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 I, global. DOI: 10.1107/S160053681002800X/wn2400sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002800X/wn2400Isup2.hkl

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

C12H8N2O4	F(000) = 2016
Mr = 244.20	Dx = 1.520 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 638 reflections
a = 16.1215 (14) Å	θ = 2.8–26.3°
b = 37.126 (3) Å	µ = 0.12 mm−1
c = 7.1317 (8) Å	T = 298 K
V = 4268.5 (7) Å3	Needle, colourless
Z = 16	0.46 × 0.17 × 0.09 mm

Bruker SMART 1000 CCD area-detector diffractometer	1023 independent reflections
Radiation source: fine-focus sealed tube	621 reflections with I > 2σ(I)
graphite	Rint = 0.110
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −19→11
Tmin = 0.948, Tmax = 0.990	k = −43→43
4377 measured reflections	l = −8→8

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0406P)2 + 0.170P] where P = (Fo2 + 2Fc2)/3
1023 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.22 e Å−3

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.

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 > 2sigma(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
N1	−0.0034 (3)	0.07102 (12)	0.9143 (9)	0.0630 (15)
N2	0.3542 (3)	−0.05673 (10)	0.8083 (7)	0.0543 (14)
H2	0.3836	−0.0760	0.8109	0.065*
O1	0.3097 (2)	0.13480 (9)	0.5977 (7)	0.0701 (13)
O2	0.2043 (2)	0.16759 (9)	0.7037 (7)	0.0731 (14)
O3	−0.0420 (2)	0.09929 (10)	0.9147 (9)	0.0919 (17)
O4	−0.0331 (2)	0.04219 (10)	0.9681 (8)	0.0856 (17)
C1	0.2386 (4)	0.13874 (13)	0.6766 (9)	0.0526 (15)
C2	0.2001 (3)	0.10398 (12)	0.7393 (8)	0.0435 (14)
C3	0.1187 (3)	0.10352 (12)	0.7997 (8)	0.0486 (15)
H3	0.0881	0.1247	0.8046	0.058*
C4	0.0835 (3)	0.07138 (12)	0.8524 (9)	0.0474 (15)
C5	0.1277 (3)	0.03937 (12)	0.8486 (8)	0.0451 (14)
H5	0.1020	0.0179	0.8822	0.054*
C6	0.2104 (3)	0.03957 (11)	0.7944 (7)	0.0403 (12)
C7	0.2461 (3)	0.07216 (11)	0.7400 (8)	0.0428 (14)
H7	0.3015	0.0727	0.7035	0.051*
C8	0.2731 (3)	−0.05830 (13)	0.7825 (8)	0.0508 (15)
H8	0.2480	−0.0807	0.7685	0.061*
C9	0.2244 (3)	−0.02788 (12)	0.7757 (8)	0.0475 (14)
H9	0.1675	−0.0300	0.7580	0.057*
C10	0.2600 (3)	0.00589 (12)	0.7950 (8)	0.0420 (13)
C11	0.3461 (3)	0.00687 (12)	0.8235 (9)	0.0522 (15)
H11	0.3734	0.0288	0.8378	0.063*
C12	0.3890 (3)	−0.02476 (13)	0.8300 (9)	0.0575 (17)
H12	0.4459	−0.0238	0.8507	0.069*

	U11	U22	U33	U12	U13	U23
N1	0.044 (3)	0.056 (3)	0.089 (4)	0.001 (2)	0.002 (3)	−0.004 (3)
N2	0.055 (3)	0.036 (2)	0.072 (4)	0.014 (2)	0.003 (3)	0.005 (3)
O1	0.063 (3)	0.041 (2)	0.106 (4)	−0.0047 (18)	0.024 (3)	0.005 (2)
O2	0.066 (3)	0.0369 (19)	0.116 (4)	0.0041 (18)	0.007 (3)	0.011 (3)
O3	0.063 (2)	0.065 (3)	0.149 (5)	0.020 (2)	0.030 (3)	0.006 (3)
O4	0.056 (2)	0.058 (2)	0.143 (5)	−0.009 (2)	0.019 (3)	0.012 (3)
C1	0.057 (4)	0.035 (3)	0.066 (4)	−0.003 (3)	0.001 (3)	0.011 (3)
C2	0.042 (3)	0.032 (2)	0.057 (4)	−0.001 (2)	−0.001 (3)	0.000 (2)
C3	0.046 (3)	0.030 (3)	0.070 (4)	0.003 (2)	−0.001 (3)	−0.002 (3)
C4	0.041 (3)	0.034 (3)	0.067 (4)	−0.001 (2)	0.000 (3)	0.000 (3)
C5	0.046 (3)	0.031 (3)	0.058 (4)	0.001 (2)	0.001 (3)	0.003 (3)
C6	0.040 (3)	0.031 (3)	0.049 (3)	−0.002 (2)	−0.001 (3)	0.000 (3)
C7	0.035 (3)	0.031 (2)	0.061 (4)	0.001 (2)	0.000 (3)	−0.001 (3)
C8	0.057 (4)	0.032 (3)	0.063 (4)	0.001 (2)	−0.003 (3)	0.008 (3)
C9	0.044 (3)	0.038 (3)	0.060 (4)	−0.004 (2)	0.001 (3)	0.001 (3)
C10	0.045 (3)	0.031 (3)	0.051 (4)	0.002 (2)	0.003 (3)	0.003 (2)
C11	0.051 (3)	0.035 (3)	0.070 (4)	−0.001 (2)	0.004 (3)	0.004 (3)
C12	0.049 (3)	0.042 (3)	0.082 (5)	0.005 (3)	0.005 (3)	0.008 (3)

N1—O3	1.220 (5)	C5—C6	1.388 (6)
N1—O4	1.233 (5)	C5—H5	0.9300
N1—C4	1.469 (7)	C6—C7	1.395 (6)
N2—C12	1.322 (6)	C6—C10	1.485 (6)
N2—C8	1.323 (6)	C7—H7	0.9300
N2—H2	0.8600	C8—C9	1.376 (6)
O1—C1	1.284 (6)	C8—H8	0.9300
O2—C1	1.221 (6)	C9—C10	1.386 (6)
C1—C2	1.500 (6)	C9—H9	0.9300
C2—C3	1.381 (7)	C10—C11	1.403 (6)
C2—C7	1.394 (6)	C11—C12	1.364 (6)
C3—C4	1.374 (6)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.386 (6)
O3—N1—O4	123.2 (5)	C5—C6—C7	118.6 (4)
O3—N1—C4	118.6 (5)	C5—C6—C10	120.8 (4)
O4—N1—C4	118.1 (4)	C7—C6—C10	120.6 (4)
C12—N2—C8	118.4 (4)	C2—C7—C6	121.1 (4)
C12—N2—H2	120.8	C2—C7—H7	119.4
C8—N2—H2	120.8	C6—C7—H7	119.4
O2—C1—O1	125.0 (5)	N2—C8—C9	122.2 (5)
O2—C1—C2	121.3 (5)	N2—C8—H8	118.9
O1—C1—C2	113.7 (4)	C9—C8—H8	118.9
C3—C2—C7	119.6 (4)	C8—C9—C10	120.2 (4)
C3—C2—C1	119.8 (4)	C8—C9—H9	119.9
C7—C2—C1	120.7 (4)	C10—C9—H9	119.9
C4—C3—C2	119.3 (4)	C9—C10—C11	116.6 (4)
C4—C3—H3	120.4	C9—C10—C6	122.6 (4)
C2—C3—H3	120.4	C11—C10—C6	120.8 (4)
C3—C4—C5	121.8 (4)	C12—C11—C10	119.0 (5)
C3—C4—N1	119.0 (4)	C12—C11—H11	120.5
C5—C4—N1	119.2 (5)	C10—C11—H11	120.5
C4—C5—C6	119.6 (4)	N2—C12—C11	123.6 (5)
C4—C5—H5	120.2	N2—C12—H12	118.2
C6—C5—H5	120.2	C11—C12—H12	118.2
O2—C1—C2—C3	11.2 (9)	C3—C2—C7—C6	2.3 (9)
O1—C1—C2—C3	−170.0 (5)	C1—C2—C7—C6	−178.7 (5)
O2—C1—C2—C7	−167.8 (6)	C5—C6—C7—C2	−0.1 (8)
O1—C1—C2—C7	10.9 (8)	C10—C6—C7—C2	−179.8 (5)
C7—C2—C3—C4	−2.6 (8)	C12—N2—C8—C9	0.7 (9)
C1—C2—C3—C4	178.4 (5)	N2—C8—C9—C10	0.4 (9)
C2—C3—C4—C5	0.7 (8)	C8—C9—C10—C11	−0.8 (8)
C2—C3—C4—N1	−179.3 (6)	C8—C9—C10—C6	−178.2 (5)
O3—N1—C4—C3	0.9 (8)	C5—C6—C10—C9	25.9 (8)
O4—N1—C4—C3	−177.2 (6)	C7—C6—C10—C9	−154.3 (5)
O3—N1—C4—C5	−179.0 (6)	C5—C6—C10—C11	−151.4 (6)
O4—N1—C4—C5	2.8 (8)	C7—C6—C10—C11	28.4 (8)
C3—C4—C5—C6	1.5 (9)	C9—C10—C11—C12	0.2 (9)
N1—C4—C5—C6	−178.5 (5)	C6—C10—C11—C12	177.6 (5)
C4—C5—C6—C7	−1.8 (8)	C8—N2—C12—C11	−1.3 (10)
C4—C5—C6—C10	178.0 (5)	C10—C11—C12—N2	0.9 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86	1.74	2.592 (5)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	1.74	2.592 (5)	172

Symmetry code: (i) .