2-(2,4-Dinitro-benz-yl)pyridinium 2-hy-droxy-3,5-dinitro-benzoate.

In the structure of the title salt, C(12)H(10)N(3)O(4) (+)·C(7)H(3)N(2)O(7) (-), the cations and the anions are linked by a single N(+)-H⋯O(carbox-yl) hydrogen bond, the discrete cation-anion unit having no inter-molecular associations other than weak cation-anion aromatic ring π-π inter-actions [ring centroid separation = 3.7320 (14) Å] and a number of weak inter-unit aromatic C-H⋯O contacts. An intramolecular C-H⋯O hydrox-yl-carboxyl hydrogen bond occurs in the anion.

Related literature

For structural data on 2-(2,4-dinitro­benz­yl)pyridine and related compounds, see: Seff & Trueblood (1968 ▶); Scherl et al. (1996 ▶); Naumov et al. (2002 ▶, 2005 ▶); Smith, Wermuth & Young (2010 ▶). For some structures of 3,5-dinitro­salicylic acid salts of Lewis bases, see: Smith et al. (2002 ▶, 2003 ▶, 2007 ▶); Smith, Cotton et al. (2010 ▶).

Experimental

Crystal data

C12H10N3O4 +·C7H3N2O7 −

M = 487.34

Monoclinic,

a = 7.1550 (2) Å

b = 21.7356 (5) Å

c = 13.2080 (4) Å

β = 104.424 (3)°

V = 1989.34 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 200 K

0.40 × 0.35 × 0.18 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.960, T max = 0.982

13759 measured reflections

3910 independent reflections

2865 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.153

S = 1.08

3910 reflections

320 parameters

H-atom parameters constrained

Δρmax = 0.75 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024888/ez2219sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024888/ez2219Isup2.hkl

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

C12H10N3O4+·C7H3N2O7−	F(000) = 1000
Mr = 487.34	Dx = 1.627 Mg m−3
Monoclinic, P21/c	Melting point: 383 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.1550 (2) Å	Cell parameters from 6248 reflections
b = 21.7356 (5) Å	θ = 3.1–28.7°
c = 13.2080 (4) Å	µ = 0.14 mm−1
β = 104.424 (3)°	T = 200 K
V = 1989.34 (10) Å3	Plate, yellow
Z = 4	0.40 × 0.35 × 0.18 mm

Oxford Diffraction Gemini-S CCD-detector diffractometer	3910 independent reflections
Radiation source: Enhance (Mo) X-ray source	2865 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 26.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→5
Tmin = 0.960, Tmax = 0.982	k = −26→26
13759 measured reflections	l = −16→16

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0819P)2 + 0.673P] where P = (Fo2 + 2Fc2)/3
3910 reflections	(Δ/σ)max < 0.001
320 parameters	Δρmax = 0.75 e Å−3
0 restraints	Δρmin = −0.32 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 e.s.d.'s 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
O21	1.2566 (3)	0.22969 (10)	0.63986 (18)	0.0562 (8)
O22	1.1932 (4)	0.18930 (12)	0.48691 (19)	0.0733 (10)
O41	0.7828 (4)	0.00564 (10)	0.43481 (18)	0.0635 (9)
O42	0.6790 (3)	−0.02169 (9)	0.56819 (19)	0.0577 (8)
N1	0.6649 (3)	0.32238 (8)	0.69232 (15)	0.0274 (6)
N21	1.1587 (3)	0.19783 (10)	0.57118 (18)	0.0365 (7)
N41	0.7462 (3)	0.01652 (11)	0.5177 (2)	0.0458 (8)
C2	0.7755 (3)	0.28074 (10)	0.75516 (18)	0.0267 (7)
C3	0.7361 (4)	0.26743 (11)	0.84941 (19)	0.0316 (7)
C4	0.5867 (4)	0.29735 (12)	0.87819 (19)	0.0345 (8)
C5	0.4801 (4)	0.34101 (12)	0.8133 (2)	0.0376 (8)
C6	0.5212 (4)	0.35297 (12)	0.7190 (2)	0.0359 (8)
C11	0.8856 (3)	0.19180 (10)	0.65949 (17)	0.0250 (7)
C21	0.9877 (3)	0.16655 (10)	0.59134 (18)	0.0268 (7)
C31	0.9395 (3)	0.11127 (11)	0.5400 (2)	0.0322 (8)
C41	0.7909 (4)	0.07812 (11)	0.5632 (2)	0.0353 (8)
C51	0.6845 (4)	0.10000 (12)	0.6292 (2)	0.0359 (8)
C61	0.7296 (3)	0.15746 (11)	0.67349 (19)	0.0307 (7)
C71	0.9381 (3)	0.25231 (10)	0.7169 (2)	0.0308 (7)
O2A	0.7053 (3)	0.51546 (8)	0.39374 (15)	0.0389 (6)
O11A	0.7728 (2)	0.34274 (8)	0.51916 (13)	0.0363 (6)
O12A	0.6246 (3)	0.43376 (8)	0.50643 (15)	0.0404 (6)
O31A	0.8926 (3)	0.60447 (8)	0.32114 (17)	0.0482 (7)
O32A	1.0404 (4)	0.57457 (11)	0.20856 (19)	0.0703 (10)
O51A	1.4121 (3)	0.38998 (10)	0.28140 (17)	0.0514 (7)
O52A	1.3387 (3)	0.32069 (9)	0.38239 (19)	0.0536 (7)
N31A	0.9667 (3)	0.56457 (10)	0.28107 (17)	0.0388 (7)
N51A	1.3139 (3)	0.37048 (10)	0.33857 (18)	0.0375 (7)
C1A	0.8825 (3)	0.42179 (10)	0.42470 (17)	0.0254 (6)
C2A	0.8508 (3)	0.48139 (11)	0.38128 (18)	0.0276 (7)
C3A	0.9808 (4)	0.50221 (10)	0.32341 (18)	0.0293 (7)
C4A	1.1287 (3)	0.46614 (11)	0.30776 (18)	0.0296 (7)
C5A	1.1555 (3)	0.40898 (11)	0.35306 (18)	0.0278 (7)
C6A	1.0358 (3)	0.38671 (10)	0.41266 (18)	0.0268 (7)
C11A	0.7494 (3)	0.39730 (11)	0.48798 (18)	0.0294 (7)
H1	0.69100	0.32880	0.62900	0.0330*
H3	0.80970	0.23840	0.89370	0.0380*
H4	0.55830	0.28790	0.94140	0.0410*
H5	0.38170	0.36210	0.83300	0.0450*
H6	0.44980	0.38210	0.67380	0.0430*
H31	1.00440	0.09700	0.49180	0.0390*
H51	0.58490	0.07680	0.64350	0.0430*
H61	0.65290	0.17380	0.71420	0.0370*
H71	1.04700	0.24550	0.77630	0.0370*
H72	0.97850	0.28120	0.67050	0.0370*
H2A	0.64800	0.49380	0.43920	0.0470*
H4A	1.20920	0.48020	0.26720	0.0350*
H6A	1.05890	0.34830	0.44430	0.0320*

	U11	U22	U33	U12	U13	U23
O21	0.0376 (11)	0.0622 (13)	0.0758 (15)	−0.0202 (10)	0.0272 (11)	−0.0216 (12)
O22	0.0767 (17)	0.0939 (18)	0.0687 (15)	−0.0332 (14)	0.0546 (14)	−0.0196 (14)
O41	0.0775 (17)	0.0640 (14)	0.0585 (14)	−0.0200 (12)	0.0349 (13)	−0.0309 (12)
O42	0.0637 (14)	0.0356 (11)	0.0721 (15)	−0.0054 (10)	0.0135 (12)	0.0012 (11)
N1	0.0292 (10)	0.0257 (9)	0.0297 (10)	−0.0008 (8)	0.0120 (9)	0.0026 (8)
N21	0.0322 (12)	0.0356 (11)	0.0477 (13)	−0.0004 (10)	0.0212 (11)	0.0017 (11)
N41	0.0363 (13)	0.0420 (13)	0.0597 (16)	−0.0027 (10)	0.0132 (12)	−0.0135 (12)
C2	0.0264 (12)	0.0207 (10)	0.0338 (13)	−0.0042 (9)	0.0093 (10)	−0.0031 (10)
C3	0.0344 (13)	0.0284 (12)	0.0306 (13)	−0.0009 (10)	0.0057 (11)	0.0015 (10)
C4	0.0373 (14)	0.0405 (14)	0.0283 (13)	−0.0064 (11)	0.0133 (11)	−0.0037 (11)
C5	0.0367 (14)	0.0408 (14)	0.0391 (14)	0.0066 (12)	0.0164 (12)	−0.0033 (12)
C6	0.0341 (13)	0.0337 (13)	0.0412 (14)	0.0074 (11)	0.0121 (12)	0.0054 (11)
C11	0.0219 (11)	0.0259 (11)	0.0270 (12)	0.0036 (9)	0.0055 (9)	0.0055 (9)
C21	0.0223 (11)	0.0304 (12)	0.0289 (12)	0.0020 (9)	0.0087 (9)	0.0049 (10)
C31	0.0296 (13)	0.0357 (13)	0.0335 (13)	0.0058 (10)	0.0121 (11)	−0.0016 (11)
C41	0.0301 (13)	0.0322 (13)	0.0440 (15)	0.0014 (10)	0.0098 (11)	−0.0072 (12)
C51	0.0292 (13)	0.0363 (13)	0.0455 (15)	−0.0065 (11)	0.0153 (12)	−0.0050 (12)
C61	0.0277 (12)	0.0289 (12)	0.0393 (13)	0.0007 (10)	0.0158 (11)	−0.0019 (11)
C71	0.0284 (12)	0.0265 (12)	0.0396 (14)	−0.0002 (10)	0.0123 (11)	0.0002 (11)
O2A	0.0345 (10)	0.0364 (10)	0.0512 (11)	0.0054 (8)	0.0209 (9)	0.0012 (8)
O11A	0.0406 (10)	0.0372 (10)	0.0350 (9)	−0.0063 (8)	0.0169 (8)	0.0018 (8)
O12A	0.0391 (10)	0.0429 (10)	0.0475 (11)	−0.0027 (8)	0.0266 (9)	−0.0072 (9)
O31A	0.0479 (12)	0.0313 (10)	0.0636 (13)	0.0026 (9)	0.0108 (11)	0.0013 (9)
O32A	0.101 (2)	0.0591 (14)	0.0630 (15)	−0.0014 (13)	0.0434 (15)	0.0203 (12)
O51A	0.0386 (11)	0.0653 (13)	0.0604 (13)	0.0026 (9)	0.0311 (10)	−0.0076 (11)
O52A	0.0403 (11)	0.0374 (11)	0.0861 (16)	0.0093 (9)	0.0215 (11)	0.0020 (11)
N31A	0.0385 (12)	0.0389 (12)	0.0385 (12)	−0.0018 (10)	0.0087 (10)	0.0062 (10)
N51A	0.0249 (11)	0.0425 (13)	0.0475 (13)	0.0001 (9)	0.0133 (10)	−0.0094 (11)
C1A	0.0254 (11)	0.0286 (11)	0.0228 (11)	−0.0030 (9)	0.0073 (9)	−0.0043 (10)
C2A	0.0258 (12)	0.0325 (12)	0.0255 (12)	−0.0010 (10)	0.0082 (10)	−0.0051 (10)
C3A	0.0316 (13)	0.0290 (12)	0.0274 (12)	−0.0018 (10)	0.0074 (10)	0.0015 (10)
C4A	0.0262 (12)	0.0385 (13)	0.0265 (12)	−0.0069 (10)	0.0113 (10)	−0.0032 (11)
C5A	0.0226 (11)	0.0327 (12)	0.0288 (12)	−0.0007 (10)	0.0076 (10)	−0.0091 (10)
C6A	0.0265 (12)	0.0273 (12)	0.0266 (11)	−0.0024 (9)	0.0065 (10)	−0.0019 (10)
C11A	0.0285 (12)	0.0352 (13)	0.0264 (12)	−0.0073 (10)	0.0104 (10)	−0.0061 (10)

O21—N21	1.215 (3)	C11—C61	1.393 (3)
O22—N21	1.213 (3)	C11—C71	1.518 (3)
O41—N41	1.211 (3)	C21—C31	1.381 (3)
O42—N41	1.235 (3)	C31—C41	1.381 (4)
O2A—C2A	1.321 (3)	C41—C51	1.377 (4)
O11A—C11A	1.253 (3)	C51—C61	1.383 (4)
O12A—C11A	1.262 (3)	C3—H3	0.9300
O31A—N31A	1.206 (3)	C4—H4	0.9300
O32A—N31A	1.222 (3)	C5—H5	0.9300
O51A—N51A	1.228 (3)	C6—H6	0.9300
O52A—N51A	1.219 (3)	C31—H31	0.9300
O2A—H2A	0.9300	C51—H51	0.9300
N1—C6	1.343 (4)	C61—H61	0.9300
N1—C2	1.344 (3)	C71—H71	0.9700
N21—C21	1.481 (3)	C71—H72	0.9700
N41—C41	1.470 (3)	C1A—C6A	1.377 (3)
N1—H1	0.9100	C1A—C11A	1.512 (3)
N31A—C3A	1.460 (3)	C1A—C2A	1.412 (3)
N51A—C5A	1.459 (3)	C2A—C3A	1.417 (4)
C2—C71	1.511 (3)	C3A—C4A	1.373 (4)
C2—C3	1.374 (3)	C4A—C5A	1.372 (3)
C3—C4	1.383 (4)	C5A—C6A	1.387 (3)
C4—C5	1.375 (4)	C4A—H4A	0.9300
C5—C6	1.374 (4)	C6A—H6A	0.9300
C11—C21	1.405 (3)
C2A—O2A—H2A	106.00	C5—C4—H4	120.00
C2—N1—C6	122.9 (2)	C3—C4—H4	120.00
O21—N21—C21	118.4 (2)	C6—C5—H5	121.00
O22—N21—C21	117.5 (2)	C4—C5—H5	120.00
O21—N21—O22	124.1 (3)	N1—C6—H6	120.00
O41—N41—O42	123.9 (2)	C5—C6—H6	120.00
O42—N41—C41	117.8 (2)	C41—C31—H31	121.00
O41—N41—C41	118.3 (2)	C21—C31—H31	121.00
C6—N1—H1	121.00	C41—C51—H51	121.00
C2—N1—H1	116.00	C61—C51—H51	121.00
O31A—N31A—O32A	122.6 (2)	C11—C61—H61	119.00
O31A—N31A—C3A	119.7 (2)	C51—C61—H61	119.00
O32A—N31A—C3A	117.6 (2)	H71—C71—H72	108.00
O51A—N51A—C5A	117.7 (2)	C2—C71—H72	109.00
O52A—N51A—C5A	118.2 (2)	C11—C71—H71	109.00
O51A—N51A—O52A	124.1 (2)	C2—C71—H71	109.00
C3—C2—C71	124.5 (2)	C11—C71—H72	109.00
N1—C2—C3	118.6 (2)	C2A—C1A—C6A	120.9 (2)
N1—C2—C71	116.9 (2)	C2A—C1A—C11A	119.2 (2)
C2—C3—C4	119.8 (2)	C6A—C1A—C11A	119.9 (2)
C3—C4—C5	120.0 (2)	O2A—C2A—C3A	122.1 (2)
C4—C5—C6	119.0 (3)	C1A—C2A—C3A	116.8 (2)
N1—C6—C5	119.7 (2)	O2A—C2A—C1A	121.0 (2)
C61—C11—C71	120.3 (2)	N31A—C3A—C2A	120.7 (2)
C21—C11—C71	123.7 (2)	C2A—C3A—C4A	122.2 (2)
C21—C11—C61	116.0 (2)	N31A—C3A—C4A	117.0 (2)
N21—C21—C11	121.4 (2)	C3A—C4A—C5A	118.7 (2)
C11—C21—C31	123.3 (2)	N51A—C5A—C6A	118.9 (2)
N21—C21—C31	115.3 (2)	C4A—C5A—C6A	121.7 (2)
C21—C31—C41	117.2 (2)	N51A—C5A—C4A	119.4 (2)
N41—C41—C51	118.4 (2)	C1A—C6A—C5A	119.6 (2)
N41—C41—C31	119.1 (2)	O11A—C11A—C1A	117.7 (2)
C31—C41—C51	122.6 (2)	O12A—C11A—C1A	117.3 (2)
C41—C51—C61	118.2 (2)	O11A—C11A—O12A	125.0 (2)
C11—C61—C51	122.6 (2)	C3A—C4A—H4A	121.00
C2—C71—C11	113.96 (18)	C5A—C4A—H4A	121.00
C2—C3—H3	120.00	C1A—C6A—H6A	120.00
C4—C3—H3	120.00	C5A—C6A—H6A	120.00
C6—N1—C2—C3	2.1 (3)	C71—C11—C61—C51	−175.1 (2)
C6—N1—C2—C71	−177.0 (2)	C21—C11—C71—C2	160.2 (2)
C2—N1—C6—C5	−1.4 (4)	C61—C11—C71—C2	−20.4 (3)
O21—N21—C21—C11	29.4 (3)	C11—C21—C31—C41	−4.3 (4)
O21—N21—C21—C31	−149.7 (2)	N21—C21—C31—C41	174.8 (2)
O22—N21—C21—C11	−151.4 (2)	C21—C31—C41—N41	−174.5 (2)
O22—N21—C21—C31	29.5 (3)	C21—C31—C41—C51	4.2 (4)
O41—N41—C41—C31	−27.8 (4)	C31—C41—C51—C61	0.0 (4)
O41—N41—C41—C51	153.4 (3)	N41—C41—C51—C61	178.7 (2)
O42—N41—C41—C31	149.9 (2)	C41—C51—C61—C11	−4.5 (4)
O42—N41—C41—C51	−28.8 (4)	C6A—C1A—C2A—O2A	−179.2 (2)
O31A—N31A—C3A—C2A	24.4 (4)	C6A—C1A—C2A—C3A	1.4 (3)
O31A—N31A—C3A—C4A	−153.3 (2)	C11A—C1A—C2A—O2A	−1.1 (3)
O32A—N31A—C3A—C2A	−159.1 (2)	C11A—C1A—C2A—C3A	179.5 (2)
O32A—N31A—C3A—C4A	23.2 (3)	C2A—C1A—C6A—C5A	−3.0 (3)
O51A—N51A—C5A—C4A	−3.5 (3)	C11A—C1A—C6A—C5A	178.9 (2)
O51A—N51A—C5A—C6A	176.6 (2)	C2A—C1A—C11A—O11A	175.0 (2)
O52A—N51A—C5A—C4A	177.6 (2)	C2A—C1A—C11A—O12A	−5.8 (3)
O52A—N51A—C5A—C6A	−2.3 (3)	C6A—C1A—C11A—O11A	−6.9 (3)
C71—C2—C3—C4	178.3 (2)	C6A—C1A—C11A—O12A	172.3 (2)
N1—C2—C71—C11	−94.0 (2)	O2A—C2A—C3A—N31A	4.4 (4)
C3—C2—C71—C11	86.9 (3)	O2A—C2A—C3A—C4A	−178.0 (2)
N1—C2—C3—C4	−0.8 (4)	C1A—C2A—C3A—N31A	−176.2 (2)
C2—C3—C4—C5	−1.1 (4)	C1A—C2A—C3A—C4A	1.4 (3)
C3—C4—C5—C6	1.7 (4)	N31A—C3A—C4A—C5A	175.2 (2)
C4—C5—C6—N1	−0.5 (4)	C2A—C3A—C4A—C5A	−2.5 (4)
C61—C11—C21—N21	−178.8 (2)	C3A—C4A—C5A—N51A	−179.0 (2)
C61—C11—C21—C31	0.2 (3)	C3A—C4A—C5A—C6A	0.9 (4)
C71—C11—C21—N21	0.6 (3)	N51A—C5A—C6A—C1A	−178.2 (2)
C71—C11—C21—C31	179.6 (2)	C4A—C5A—C6A—C1A	1.9 (4)
C21—C11—C61—C51	4.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O11A	0.91	1.72	2.627 (3)	172
O2A—H2A···O12A	0.93	1.61	2.476 (3)	152
C3—H3···O11Ai	0.93	2.48	3.246 (3)	140
C5—H5···O31Aii	0.93	2.56	3.051 (4)	114
C6—H6···O31Aii	0.93	2.48	3.020 (4)	117
C51—H51···O51Aiii	0.93	2.55	3.137 (4)	122
C61—H61···O51Aiii	0.93	2.54	3.141 (3)	123
C71—H72···O11A	0.97	2.55	3.247 (3)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O11A	0.91	1.72	2.627 (3)	172
O2A—H2A⋯O12A	0.93	1.61	2.476 (3)	152
C3—H3⋯O11Ai	0.93	2.48	3.246 (3)	140
C5—H5⋯O31Aii	0.93	2.56	3.051 (4)	114
C6—H6⋯O31Aii	0.93	2.48	3.020 (4)	117
C51—H51⋯O51Aiii	0.93	2.55	3.137 (4)	122
C61—H61⋯O51Aiii	0.93	2.54	3.141 (3)	123
C71—H72⋯O11A	0.97	2.55	3.247 (3)	129

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