2-[(Pyridin-2-yl)amino]-pyridinium 2,4,6-tri-nitro-phenolate.

In the cation of the title salt, C10H10N3 (+)·C6H2N3O7 (-), the pyridine and pyridinium rings are linked by an intra-molecular N-H⋯N hydrogen bond and are approximately coplanar, with a dihedral angle between their planes of 4.24 (6)°. In the crystal, the cations and anions are linked through N-H⋯O hydrogen bonds, forming supra-molecular chains propagating along the c-axis direction. π-π stacking is observed between neighbouring chains, the centroid-centroid distances being 3.7638 (11) (between pyridinium rings) and 3.5331 (11) Å (between benzene rings).

Related literature

For uses of picric acid and picrates, see: Shriner et al. (1980 ▶); In et al. (1997 ▶); Zaderenko et al. (1997 ▶). For related structures, see: Fritsky et al. (2006 ▶); Moroz et al. (2012 ▶); Penkova et al. (2009 ▶); Golenya et al. (2012 ▶).

Experimental

Crystal data

C10H10N3 +·C6H2N3O7 −

M = 400.32

Monoclinic,

a = 9.1807 (8) Å

b = 14.5892 (12) Å

c = 13.1649 (10) Å

β = 108.925 (2)°

V = 1668.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 100 K

0.25 × 0.21 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.974, T max = 0.983

10460 measured reflections

3253 independent reflections

2674 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.102

S = 1.03

3253 reflections

270 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814012835/xu5794sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012835/xu5794Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814012835/xu5794Isup3.cml

CCDC reference: 1006378

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H10N3+·C6H2N3O7−	F(000) = 824
Mr = 400.32	Dx = 1.594 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3858 reflections
a = 9.1807 (8) Å	θ = 2.4–29.9°
b = 14.5892 (12) Å	µ = 0.13 mm−1
c = 13.1649 (10) Å	T = 100 K
β = 108.925 (2)°	Block, yellow
V = 1668.0 (2) Å3	0.25 × 0.21 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3253 independent reflections
Radiation source: fine-focus sealed tube	2674 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.029
Detector resolution: 16 pixels mm-1	θmax = 26.0°, θmin = 2.2°
φ scans and ω scans with κ offset	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −17→16
Tmin = 0.974, Tmax = 0.983	l = −16→16
10460 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0416P)2 + 1.2391P] where P = (Fo2 + 2Fc2)/3
3253 reflections	(Δ/σ)max < 0.001
270 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.55 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
O1	0.10222 (15)	0.54091 (9)	−0.17771 (10)	0.0236 (3)
O2	−0.06688 (18)	0.69273 (10)	−0.18938 (11)	0.0323 (4)
O3	−0.16715 (15)	0.69936 (9)	−0.06137 (11)	0.0259 (3)
O4	0.15975 (16)	0.63990 (10)	0.29479 (10)	0.0279 (3)
O5	0.35245 (15)	0.54601 (10)	0.32327 (10)	0.0282 (3)
O6	0.46259 (16)	0.40445 (10)	0.03187 (11)	0.0289 (3)
O7	0.2807 (2)	0.39426 (15)	−0.11952 (13)	0.0702 (7)
N1	−0.01574 (18)	0.88497 (10)	−0.04563 (12)	0.0176 (3)
H1N	0.079 (3)	0.8656 (16)	−0.0451 (18)	0.036 (6)*
N2	0.08719 (18)	0.86091 (11)	0.14029 (12)	0.0199 (3)
H2N	0.075 (2)	0.8730 (15)	0.2019 (18)	0.027 (6)*
N3	0.26368 (18)	0.82539 (11)	0.05248 (12)	0.0213 (4)
N4	−0.06696 (18)	0.67256 (11)	−0.09846 (12)	0.0212 (3)
N5	0.24186 (18)	0.58829 (11)	0.26247 (12)	0.0210 (4)
N6	0.3395 (2)	0.42975 (12)	−0.03160 (13)	0.0288 (4)
C1	−0.1325 (2)	0.90766 (13)	−0.13575 (14)	0.0206 (4)
H1	−0.1166	0.9064	−0.2035	0.025*
C2	−0.2720 (2)	0.93213 (13)	−0.12947 (15)	0.0232 (4)
H2	−0.3541	0.9481	−0.1923	0.028*
C3	−0.2925 (2)	0.93344 (13)	−0.02863 (15)	0.0238 (4)
H3	−0.3894	0.9507	−0.0230	0.029*
C4	−0.1746 (2)	0.91021 (13)	0.06177 (15)	0.0216 (4)
H4	−0.1889	0.9113	0.1300	0.026*
C5	−0.0325 (2)	0.88481 (12)	0.05260 (14)	0.0173 (4)
C6	0.2352 (2)	0.83475 (12)	0.14498 (15)	0.0192 (4)
C7	0.3446 (2)	0.81826 (13)	0.24528 (15)	0.0242 (4)
H7	0.3202	0.8258	0.3096	0.029*
C8	0.4886 (2)	0.79074 (14)	0.24768 (17)	0.0292 (5)
H8	0.5662	0.7791	0.3144	0.035*
C9	0.5205 (2)	0.77997 (14)	0.15200 (18)	0.0304 (5)
H9	0.6193	0.7604	0.1522	0.036*
C10	0.4057 (2)	0.79824 (14)	0.05736 (17)	0.0278 (5)
H10	0.4277	0.7914	−0.0079	0.033*
C11	0.1351 (2)	0.55224 (12)	−0.07926 (14)	0.0170 (4)
C12	0.0569 (2)	0.61648 (12)	−0.02980 (14)	0.0171 (4)
C13	0.0877 (2)	0.62673 (12)	0.07851 (14)	0.0176 (4)
H13	0.0282	0.6674	0.1055	0.021*
C14	0.2068 (2)	0.57704 (12)	0.14803 (14)	0.0180 (4)
C15	0.2908 (2)	0.51464 (13)	0.10980 (14)	0.0188 (4)
H15	0.3731	0.4814	0.1584	0.023*
C16	0.2538 (2)	0.50156 (12)	0.00165 (14)	0.0190 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0346 (8)	0.0227 (7)	0.0129 (6)	0.0057 (6)	0.0068 (6)	0.0021 (6)
O2	0.0471 (9)	0.0303 (8)	0.0171 (7)	0.0138 (7)	0.0070 (6)	0.0061 (6)
O3	0.0236 (7)	0.0218 (7)	0.0316 (8)	0.0031 (6)	0.0082 (6)	−0.0005 (6)
O4	0.0306 (8)	0.0354 (8)	0.0201 (7)	−0.0002 (6)	0.0116 (6)	−0.0062 (6)
O5	0.0250 (7)	0.0407 (9)	0.0158 (7)	0.0015 (6)	0.0021 (6)	0.0036 (6)
O6	0.0269 (8)	0.0336 (8)	0.0272 (7)	0.0120 (6)	0.0102 (6)	0.0095 (6)
O7	0.0931 (15)	0.0786 (14)	0.0221 (9)	0.0595 (12)	−0.0045 (9)	−0.0153 (9)
N1	0.0190 (8)	0.0170 (8)	0.0162 (8)	−0.0009 (6)	0.0052 (6)	−0.0003 (6)
N2	0.0224 (8)	0.0240 (8)	0.0132 (8)	0.0013 (7)	0.0056 (6)	−0.0013 (7)
N3	0.0222 (8)	0.0207 (8)	0.0215 (8)	−0.0001 (7)	0.0076 (7)	−0.0024 (7)
N4	0.0242 (8)	0.0166 (8)	0.0195 (8)	−0.0003 (7)	0.0026 (7)	−0.0029 (7)
N5	0.0212 (8)	0.0256 (8)	0.0161 (8)	−0.0062 (7)	0.0060 (7)	−0.0018 (7)
N6	0.0354 (10)	0.0328 (10)	0.0180 (8)	0.0142 (8)	0.0084 (7)	0.0023 (8)
C1	0.0252 (10)	0.0201 (9)	0.0147 (9)	−0.0021 (8)	0.0041 (7)	0.0006 (8)
C2	0.0225 (10)	0.0226 (10)	0.0213 (10)	0.0005 (8)	0.0025 (8)	0.0025 (8)
C3	0.0215 (10)	0.0228 (10)	0.0271 (10)	0.0009 (8)	0.0079 (8)	−0.0010 (8)
C4	0.0255 (10)	0.0215 (10)	0.0191 (9)	−0.0008 (8)	0.0092 (8)	−0.0023 (8)
C5	0.0228 (10)	0.0128 (8)	0.0155 (9)	−0.0028 (7)	0.0051 (7)	−0.0021 (7)
C6	0.0207 (9)	0.0141 (9)	0.0203 (9)	−0.0014 (7)	0.0034 (7)	−0.0025 (7)
C7	0.0271 (10)	0.0220 (10)	0.0197 (9)	−0.0001 (8)	0.0023 (8)	−0.0029 (8)
C8	0.0252 (11)	0.0229 (10)	0.0302 (11)	0.0018 (8)	−0.0036 (8)	−0.0031 (9)
C9	0.0208 (10)	0.0276 (11)	0.0399 (12)	0.0017 (8)	0.0059 (9)	−0.0076 (10)
C10	0.0273 (11)	0.0266 (11)	0.0316 (11)	0.0019 (9)	0.0124 (9)	−0.0043 (9)
C11	0.0199 (9)	0.0150 (9)	0.0154 (9)	−0.0033 (7)	0.0049 (7)	0.0012 (7)
C12	0.0171 (9)	0.0147 (9)	0.0178 (9)	−0.0023 (7)	0.0032 (7)	0.0002 (7)
C13	0.0182 (9)	0.0160 (9)	0.0196 (9)	−0.0043 (7)	0.0074 (7)	−0.0022 (7)
C14	0.0192 (9)	0.0209 (9)	0.0140 (9)	−0.0046 (7)	0.0057 (7)	−0.0019 (7)
C15	0.0156 (9)	0.0222 (9)	0.0172 (9)	−0.0014 (7)	0.0034 (7)	0.0022 (8)
C16	0.0200 (9)	0.0208 (9)	0.0173 (9)	0.0001 (8)	0.0074 (8)	0.0001 (8)

O1—C11	1.243 (2)	C2—H2	0.9500
O2—N4	1.233 (2)	C3—C4	1.367 (3)
O3—N4	1.237 (2)	C3—H3	0.9500
O4—N5	1.235 (2)	C4—C5	1.398 (3)
O5—N5	1.235 (2)	C4—H4	0.9500
O6—N6	1.224 (2)	C6—C7	1.396 (3)
O7—N6	1.222 (2)	C7—C8	1.371 (3)
N1—C5	1.351 (2)	C7—H7	0.9500
N1—C1	1.357 (2)	C8—C9	1.392 (3)
N1—H1N	0.92 (2)	C8—H8	0.9500
N2—C5	1.356 (2)	C9—C10	1.372 (3)
N2—C6	1.394 (2)	C9—H9	0.9500
N2—H2N	0.87 (2)	C10—H10	0.9500
N3—C6	1.333 (2)	C11—C16	1.455 (3)
N3—C10	1.345 (2)	C11—C12	1.456 (2)
N4—C12	1.454 (2)	C12—C13	1.369 (2)
N5—C14	1.444 (2)	C13—C14	1.382 (3)
N6—C16	1.460 (2)	C13—H13	0.9500
C1—C2	1.358 (3)	C14—C15	1.388 (3)
C1—H1	0.9500	C15—C16	1.366 (2)
C2—C3	1.400 (3)	C15—H15	0.9500
C5—N1—C1	122.30 (16)	N3—C6—C7	123.52 (17)
C5—N1—H1N	113.4 (14)	N2—C6—C7	118.76 (17)
C1—N1—H1N	124.3 (14)	C8—C7—C6	117.67 (18)
C5—N2—C6	128.13 (16)	C8—C7—H7	121.2
C5—N2—H2N	115.1 (14)	C6—C7—H7	121.2
C6—N2—H2N	115.7 (14)	C7—C8—C9	119.76 (19)
C6—N3—C10	117.47 (16)	C7—C8—H8	120.1
O2—N4—O3	122.87 (16)	C9—C8—H8	120.1
O2—N4—C12	119.43 (15)	C10—C9—C8	118.38 (19)
O3—N4—C12	117.69 (15)	C10—C9—H9	120.8
O4—N5—O5	123.15 (15)	C8—C9—H9	120.8
O4—N5—C14	118.32 (15)	N3—C10—C9	123.21 (19)
O5—N5—C14	118.53 (15)	N3—C10—H10	118.4
O7—N6—O6	123.04 (17)	C9—C10—H10	118.4
O7—N6—C16	118.18 (16)	O1—C11—C16	124.53 (16)
O6—N6—C16	118.66 (16)	O1—C11—C12	124.32 (16)
N1—C1—C2	120.28 (17)	C16—C11—C12	111.13 (15)
N1—C1—H1	119.9	C13—C12—N4	116.22 (16)
C2—C1—H1	119.9	C13—C12—C11	124.81 (16)
C1—C2—C3	118.75 (17)	N4—C12—C11	118.93 (15)
C1—C2—H2	120.6	C12—C13—C14	118.97 (17)
C3—C2—H2	120.6	C12—C13—H13	120.5
C4—C3—C2	120.68 (18)	C14—C13—H13	120.5
C4—C3—H3	119.7	C13—C14—C15	121.12 (16)
C2—C3—H3	119.7	C13—C14—N5	119.48 (16)
C3—C4—C5	119.23 (17)	C15—C14—N5	119.38 (16)
C3—C4—H4	120.4	C16—C15—C14	119.34 (17)
C5—C4—H4	120.4	C16—C15—H15	120.3
N1—C5—N2	120.20 (16)	C14—C15—H15	120.3
N1—C5—C4	118.76 (16)	C15—C16—C11	124.48 (16)
N2—C5—C4	121.04 (16)	C15—C16—N6	115.91 (16)
N3—C6—N2	117.71 (16)	C11—C16—N6	119.59 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N3	0.92 (2)	1.86 (2)	2.618 (2)	139 (2)
N1—H1N···O4i	0.92 (2)	2.45 (2)	3.056 (2)	123.8 (17)
N2—H2N···O1ii	0.87 (2)	1.97 (2)	2.756 (2)	149 (2)
N2—H2N···O2ii	0.87 (2)	2.42 (2)	3.114 (2)	136.6 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N3	0.92 (2)	1.86 (2)	2.618 (2)	139 (2)
N1—H1N⋯O4i	0.92 (2)	2.45 (2)	3.056 (2)	123.8 (17)
N2—H2N⋯O1ii	0.87 (2)	1.97 (2)	2.756 (2)	149 (2)
N2—H2N⋯O2ii	0.87 (2)	2.42 (2)	3.114 (2)	136.6 (18)

Symmetry codes: (i) ; (ii) .