4-(4-Nitro-benz-yl)pyridinium 5-nitro-salicylate.

In the title salt, C(12)H(11)N(2)O(2) (+)·C(7)H(4)NO(5) (-), the cations and anions inter-act through asymmetric cyclic pyridinium-carboxyl-ate N-H⋯O,O' hydrogen-bonding associations [graph set R(1) (2)(4)], giving discrete heterodimers having weak cation-anion π-π aromatic ring inter-actions [minimum ring centroid separation = 3.7116 (9) Å].

Related literature

For structural data on nitro-substituted 4-benzyl­pyridines and related compounds, see Seff & Trueblood (1968 ▶); Ottersen & Seff (1974 ▶); Scherl et al. (1996 ▶); Smith et al. (1997 ▶); Naumov et al. (2002 ▶). For structures of Lewis base salts of 5-nitro­salicylic acid, see: Smith et al. (1996 ▶, 2005 ▶, 2006 ▶). For graph-set motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C12H11N2O2 +·C7H4NO5 −

M = 397.34

Triclinic,

a = 8.3287 (5) Å

b = 10.8219 (7) Å

c = 11.3896 (8) Å

α = 65.160 (6)°

β = 88.286 (5)°

γ = 70.553 (6)°

V = 871.17 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 200 K

0.25 × 0.25 × 0.20 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.795, T max = 0.900

10797 measured reflections

3419 independent reflections

2615 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.091

S = 1.03

3419 reflections

270 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within WinGX (Farrugia, 1999 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014698/pv2273sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014698/pv2273Isup2.hkl

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

C12H11N2O2+·C7H4NO5−	Z = 2
Mr = 397.34	F(000) = 412
Triclinic, P1	Dx = 1.515 Mg m−3
Hall symbol: -P 1	Melting point = 416–417 K
a = 8.3287 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8219 (7) Å	Cell parameters from 5316 reflections
c = 11.3896 (8) Å	θ = 3.5–27.3°
α = 65.160 (6)°	µ = 0.12 mm−1
β = 88.286 (5)°	T = 200 K
γ = 70.553 (6)°	Block, yellow
V = 871.17 (12) Å3	0.25 × 0.25 × 0.20 mm

Oxford Diffraction Gemini-S CCD-detector diffractometer	3419 independent reflections
Radiation source: Enhance (Mo) X-ray source	2615 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 26.0°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.795, Tmax = 0.900	k = −13→13
10797 measured reflections	l = −14→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0545P)2] where P = (Fo2 + 2Fc2)/3
3419 reflections	(Δ/σ)max = 0.001
270 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
O41	0.59084 (14)	0.14581 (11)	0.23776 (10)	0.0489 (4)
O42	0.42667 (14)	0.05808 (12)	0.17918 (10)	0.0510 (4)
N1	0.16696 (14)	0.34798 (12)	0.86559 (10)	0.0324 (4)
N41	0.46108 (16)	0.11510 (12)	0.24364 (11)	0.0383 (4)
C2	0.23613 (17)	0.20902 (15)	0.88611 (13)	0.0337 (4)
C3	0.18362 (17)	0.16091 (14)	0.80647 (12)	0.0320 (4)
C4	0.05789 (16)	0.25761 (14)	0.70081 (12)	0.0289 (4)
C5	−0.01214 (17)	0.40136 (14)	0.68153 (13)	0.0316 (4)
C6	0.04413 (18)	0.44346 (15)	0.76571 (13)	0.0346 (4)
C11	0.12505 (16)	0.18753 (13)	0.51267 (12)	0.0283 (4)
C21	0.28151 (17)	0.20737 (14)	0.51098 (12)	0.0308 (4)
C31	0.39116 (17)	0.18636 (14)	0.42196 (12)	0.0319 (4)
C41	0.34282 (17)	0.14340 (13)	0.33503 (12)	0.0308 (4)
C42	0.00262 (17)	0.20617 (16)	0.61020 (13)	0.0363 (5)
C51	0.18791 (18)	0.12374 (14)	0.33259 (13)	0.0360 (4)
C61	0.07906 (17)	0.14782 (14)	0.42063 (13)	0.0342 (4)
O2A	0.08063 (12)	0.85096 (11)	0.92983 (10)	0.0424 (3)
O11A	0.28861 (12)	0.41609 (10)	1.02623 (9)	0.0375 (3)
O12A	0.11745 (14)	0.63753 (11)	0.88914 (10)	0.0477 (4)
O51A	0.63063 (13)	0.55882 (12)	1.41523 (10)	0.0484 (4)
O52A	0.65275 (13)	0.37091 (12)	1.38388 (11)	0.0512 (4)
N5A	0.58706 (15)	0.50136 (14)	1.35463 (11)	0.0362 (4)
C1A	0.28307 (16)	0.61579 (14)	1.06572 (12)	0.0282 (4)
C2A	0.20276 (17)	0.76553 (14)	1.03229 (13)	0.0318 (4)
C3A	0.24883 (18)	0.82552 (15)	1.10787 (13)	0.0363 (4)
C4A	0.37383 (17)	0.73914 (15)	1.21296 (13)	0.0346 (5)
C5A	0.45327 (16)	0.59222 (14)	1.24384 (12)	0.0303 (4)
C6A	0.40963 (16)	0.53007 (14)	1.17166 (12)	0.0279 (4)
C11A	0.22703 (17)	0.55144 (15)	0.98847 (13)	0.0316 (4)
H1	0.213 (2)	0.3733 (19)	0.9259 (18)	0.074 (6)*
H2	0.32160	0.14400	0.95590	0.0400*
H3	0.23190	0.06350	0.82290	0.0380*
H5	−0.09690	0.46890	0.61180	0.0380*
H6	−0.00380	0.53970	0.75310	0.0420*
H21	0.31330	0.23530	0.57090	0.0370*
H31	0.49520	0.20090	0.42090	0.0380*
H51	0.15750	0.09490	0.27290	0.0430*
H61	−0.02710	0.13740	0.41850	0.0410*
H421	−0.10870	0.27540	0.56260	0.0440*
H422	−0.01130	0.11370	0.66220	0.0440*
H2A	0.078 (3)	0.773 (2)	0.9050 (19)	0.091 (7)*
H3A	0.19460	0.92380	1.08670	0.0440*
H4A	0.40530	0.77840	1.26320	0.0420*
H6A	0.46480	0.43160	1.19400	0.0340*

	U11	U22	U33	U12	U13	U23
O41	0.0475 (7)	0.0522 (7)	0.0479 (7)	−0.0139 (5)	0.0127 (5)	−0.0259 (5)
O42	0.0613 (7)	0.0543 (7)	0.0382 (6)	−0.0051 (5)	−0.0024 (5)	−0.0320 (5)
N1	0.0377 (6)	0.0375 (7)	0.0289 (6)	−0.0167 (5)	0.0056 (5)	−0.0181 (5)
N41	0.0443 (7)	0.0313 (6)	0.0287 (6)	−0.0011 (6)	−0.0020 (5)	−0.0124 (5)
C2	0.0347 (7)	0.0353 (8)	0.0267 (7)	−0.0090 (6)	−0.0010 (6)	−0.0118 (6)
C3	0.0368 (8)	0.0297 (7)	0.0299 (7)	−0.0101 (6)	0.0025 (6)	−0.0145 (6)
C4	0.0295 (7)	0.0364 (7)	0.0256 (7)	−0.0153 (6)	0.0062 (5)	−0.0153 (6)
C5	0.0303 (7)	0.0326 (7)	0.0279 (7)	−0.0082 (6)	0.0009 (5)	−0.0115 (6)
C6	0.0394 (8)	0.0304 (7)	0.0346 (8)	−0.0123 (6)	0.0076 (6)	−0.0149 (6)
C11	0.0344 (7)	0.0232 (7)	0.0253 (7)	−0.0088 (6)	−0.0029 (5)	−0.0093 (5)
C21	0.0395 (8)	0.0313 (7)	0.0274 (7)	−0.0154 (6)	0.0006 (6)	−0.0155 (6)
C31	0.0362 (7)	0.0320 (7)	0.0292 (7)	−0.0137 (6)	0.0011 (6)	−0.0134 (6)
C41	0.0375 (7)	0.0241 (7)	0.0245 (7)	−0.0033 (6)	−0.0016 (6)	−0.0103 (5)
C42	0.0364 (8)	0.0465 (9)	0.0350 (8)	−0.0190 (7)	0.0028 (6)	−0.0226 (7)
C51	0.0428 (8)	0.0354 (8)	0.0318 (7)	−0.0081 (6)	−0.0080 (6)	−0.0199 (6)
C61	0.0343 (8)	0.0350 (7)	0.0352 (7)	−0.0115 (6)	−0.0047 (6)	−0.0171 (6)
O2A	0.0421 (6)	0.0345 (6)	0.0410 (6)	−0.0050 (5)	−0.0063 (5)	−0.0134 (5)
O11A	0.0435 (6)	0.0341 (6)	0.0381 (6)	−0.0102 (4)	−0.0051 (4)	−0.0205 (5)
O12A	0.0556 (7)	0.0421 (6)	0.0397 (6)	−0.0083 (5)	−0.0168 (5)	−0.0181 (5)
O51A	0.0545 (7)	0.0607 (7)	0.0454 (6)	−0.0312 (6)	−0.0048 (5)	−0.0280 (5)
O52A	0.0475 (6)	0.0438 (6)	0.0574 (7)	−0.0075 (5)	−0.0177 (5)	−0.0226 (6)
N5A	0.0347 (6)	0.0464 (8)	0.0363 (7)	−0.0208 (6)	0.0015 (5)	−0.0210 (6)
C1A	0.0273 (7)	0.0331 (7)	0.0287 (7)	−0.0131 (6)	0.0066 (5)	−0.0160 (6)
C2A	0.0299 (7)	0.0330 (7)	0.0321 (7)	−0.0115 (6)	0.0056 (6)	−0.0136 (6)
C3A	0.0403 (8)	0.0310 (7)	0.0426 (8)	−0.0146 (6)	0.0090 (6)	−0.0193 (7)
C4A	0.0385 (8)	0.0409 (8)	0.0385 (8)	−0.0217 (7)	0.0100 (6)	−0.0245 (7)
C5A	0.0272 (7)	0.0379 (8)	0.0314 (7)	−0.0153 (6)	0.0041 (5)	−0.0174 (6)
C6A	0.0271 (7)	0.0307 (7)	0.0296 (7)	−0.0122 (6)	0.0042 (5)	−0.0149 (6)
C11A	0.0317 (7)	0.0382 (8)	0.0286 (7)	−0.0131 (6)	0.0040 (6)	−0.0173 (6)

O41—N41	1.2244 (19)	C41—C51	1.379 (2)
O42—N41	1.2300 (18)	C51—C61	1.380 (2)
O2A—C2A	1.3378 (18)	C2—H2	0.9300
O11A—C11A	1.256 (2)	C3—H3	0.9300
O12A—C11A	1.2613 (18)	C5—H5	0.9300
O51A—N5A	1.2331 (19)	C6—H6	0.9300
O52A—N5A	1.227 (2)	C21—H21	0.9300
O2A—H2A	1.00 (2)	C31—H31	0.9300
N1—C6	1.3366 (18)	C42—H421	0.9700
N1—C2	1.336 (2)	C42—H422	0.9700
N41—C41	1.4673 (19)	C51—H51	0.9300
N1—H1	0.97 (2)	C61—H61	0.9300
N5A—C5A	1.4536 (18)	C1A—C6A	1.3828 (19)
C2—C3	1.363 (2)	C1A—C11A	1.494 (2)
C3—C4	1.3884 (19)	C1A—C2A	1.412 (2)
C4—C42	1.506 (2)	C2A—C3A	1.402 (2)
C4—C5	1.387 (2)	C3A—C4A	1.370 (2)
C5—C6	1.372 (2)	C4A—C5A	1.390 (2)
C11—C61	1.394 (2)	C5A—C6A	1.380 (2)
C11—C21	1.388 (2)	C3A—H3A	0.9300
C11—C42	1.516 (2)	C4A—H4A	0.9300
C21—C31	1.383 (2)	C6A—H6A	0.9300
C31—C41	1.376 (2)
C2A—O2A—H2A	97.0 (12)	C5—C6—H6	120.00
C2—N1—C6	120.47 (13)	C11—C21—H21	119.00
O41—N41—C41	118.56 (12)	C31—C21—H21	119.00
O42—N41—C41	118.07 (13)	C41—C31—H31	121.00
O41—N41—O42	123.34 (13)	C21—C31—H31	121.00
C6—N1—H1	123.7 (12)	C4—C42—H421	109.00
C2—N1—H1	115.8 (12)	C4—C42—H422	109.00
O52A—N5A—C5A	118.88 (13)	C11—C42—H421	109.00
O51A—N5A—O52A	122.56 (13)	C11—C42—H422	109.00
O51A—N5A—C5A	118.56 (14)	H421—C42—H422	108.00
N1—C2—C3	121.14 (13)	C61—C51—H51	121.00
C2—C3—C4	119.88 (14)	C41—C51—H51	121.00
C3—C4—C5	117.93 (13)	C11—C61—H61	119.00
C5—C4—C42	121.87 (12)	C51—C61—H61	119.00
C3—C4—C42	120.20 (14)	C2A—C1A—C11A	119.62 (12)
C4—C5—C6	119.72 (13)	C6A—C1A—C11A	120.95 (14)
N1—C6—C5	120.84 (15)	C2A—C1A—C6A	119.41 (13)
C21—C11—C61	118.29 (13)	O2A—C2A—C1A	120.58 (13)
C42—C11—C61	118.58 (13)	O2A—C2A—C3A	119.38 (14)
C21—C11—C42	123.13 (12)	C1A—C2A—C3A	120.04 (13)
C11—C21—C31	121.31 (13)	C2A—C3A—C4A	119.91 (15)
C21—C31—C41	118.51 (14)	C3A—C4A—C5A	119.44 (14)
N41—C41—C31	119.00 (13)	N5A—C5A—C6A	118.90 (14)
C31—C41—C51	122.04 (13)	C4A—C5A—C6A	121.88 (13)
N41—C41—C51	118.94 (12)	N5A—C5A—C4A	119.22 (13)
C4—C42—C11	114.93 (12)	C1A—C6A—C5A	119.31 (14)
C41—C51—C61	118.52 (13)	O11A—C11A—C1A	118.90 (12)
C11—C61—C51	121.28 (14)	O12A—C11A—C1A	117.35 (14)
N1—C2—H2	119.00	O11A—C11A—O12A	123.74 (14)
C3—C2—H2	119.00	C2A—C3A—H3A	120.00
C4—C3—H3	120.00	C4A—C3A—H3A	120.00
C2—C3—H3	120.00	C3A—C4A—H4A	120.00
C4—C5—H5	120.00	C5A—C4A—H4A	120.00
C6—C5—H5	120.00	C1A—C6A—H6A	120.00
N1—C6—H6	120.00	C5A—C6A—H6A	120.00
C6—N1—C2—C3	−0.1 (2)	C11—C21—C31—C41	−0.7 (2)
C2—N1—C6—C5	−0.7 (2)	C21—C31—C41—N41	−177.57 (13)
O41—N41—C41—C31	−7.89 (19)	C21—C31—C41—C51	1.3 (2)
O41—N41—C41—C51	173.20 (13)	C31—C41—C51—C61	−0.2 (2)
O42—N41—C41—C31	170.27 (13)	N41—C41—C51—C61	178.73 (13)
O42—N41—C41—C51	−8.65 (19)	C41—C51—C61—C11	−1.6 (2)
O52A—N5A—C5A—C4A	177.68 (13)	C6A—C1A—C2A—O2A	179.64 (13)
O52A—N5A—C5A—C6A	−2.8 (2)	C6A—C1A—C2A—C3A	−1.4 (2)
O51A—N5A—C5A—C4A	−2.7 (2)	C11A—C1A—C2A—O2A	−2.0 (2)
O51A—N5A—C5A—C6A	176.89 (13)	C11A—C1A—C2A—C3A	177.02 (13)
N1—C2—C3—C4	1.0 (2)	C2A—C1A—C6A—C5A	0.9 (2)
C2—C3—C4—C42	178.32 (13)	C11A—C1A—C6A—C5A	−177.44 (13)
C2—C3—C4—C5	−1.0 (2)	C2A—C1A—C11A—O11A	−173.72 (13)
C3—C4—C5—C6	0.2 (2)	C2A—C1A—C11A—O12A	5.3 (2)
C42—C4—C5—C6	−179.08 (13)	C6A—C1A—C11A—O11A	4.6 (2)
C3—C4—C42—C11	−77.72 (17)	C6A—C1A—C11A—O12A	−176.38 (13)
C5—C4—C42—C11	101.54 (17)	O2A—C2A—C3A—C4A	−179.94 (14)
C4—C5—C6—N1	0.6 (2)	C1A—C2A—C3A—C4A	1.1 (2)
C61—C11—C21—C31	−1.0 (2)	C2A—C3A—C4A—C5A	−0.3 (2)
C21—C11—C42—C4	3.8 (2)	C3A—C4A—C5A—N5A	179.37 (13)
C61—C11—C42—C4	−176.59 (13)	C3A—C4A—C5A—C6A	−0.2 (2)
C21—C11—C61—C51	2.2 (2)	N5A—C5A—C6A—C1A	−179.70 (12)
C42—C11—C21—C31	178.66 (14)	C4A—C5A—C6A—C1A	−0.2 (2)
C42—C11—C61—C51	−177.47 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O11A	0.97 (2)	1.612 (19)	2.5804 (16)	180 (2)
N1—H1···O12A	0.97 (2)	2.55 (2)	3.1464 (18)	120.2 (14)
O2A—H2A···O12A	1.00 (2)	1.48 (2)	2.4623 (17)	165 (2)
C2—H2···O42i	0.93	2.39	3.2153 (17)	148
C6—H6···O12A	0.93	2.59	3.185 (2)	122
C21—H21···O51Aii	0.93	2.49	3.271 (2)	142
C31—H31···O52Aiii	0.93	2.49	3.322 (2)	149
C42—H421···O52Aiv	0.97	2.50	3.3828 (19)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O11A	0.97 (2)	1.612 (19)	2.5804 (16)	180 (2)
N1—H1⋯O12A	0.97 (2)	2.55 (2)	3.1464 (18)	120.2 (14)
O2A—H2A⋯O12A	1.00 (2)	1.48 (2)	2.4623 (17)	165 (2)