3-(1H-Tetra-zol-5-yl)pyridinium 3-(2H-tetra-zol-5-yl)pyridinium dinitrate.

In the title compound, C(6)H(6)N(5) (+)·NO(3) (-), there are two different isomers of the cation within the asymmetric unit. The dihedral angles between the the pyridinium and tetra-zole rings are 2.54 (15) and 13.36 (18)° in the two cations. In the crystal, the packing of ions is stabilized by N-H⋯O and N-H⋯(O,O) hydrogen bonds, forming clusters composed of four ion pairs.

Related literature

For background to tetra­zole derivatives, see: Dai & Fu (2008 ▶); Wang et al. (2005 ▶); Wen (2008 ▶); Xiong et al. (2002 ▶).

Experimental

Crystal data

C6H6N5 +·NO3 −

M = 210.17

Triclinic,

a = 6.9157 (14) Å

b = 10.575 (2) Å

c = 13.346 (3) Å

α = 110.10 (3)°

β = 100.65 (3)°

γ = 95.87 (3)°

V = 886.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 298 K

0.35 × 0.30 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.956, T max = 0.981

9175 measured reflections

4035 independent reflections

2272 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.150

S = 1.03

4035 reflections

279 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901839X/hb2945sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901839X/hb2945Isup2.hkl

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

C6H6N5+·NO3−	Z = 4
Mr = 210.17	F(000) = 432
Triclinic, P1	Dx = 1.575 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9157 (14) Å	Cell parameters from 4035 reflections
b = 10.575 (2) Å	θ = 3.1–27.5°
c = 13.346 (3) Å	µ = 0.13 mm−1
α = 110.10 (3)°	T = 298 K
β = 100.65 (3)°	Block, colourless
γ = 95.87 (3)°	0.35 × 0.30 × 0.15 mm
V = 886.2 (3) Å3

Rigaku Mercury2 diffractometer	4035 independent reflections
Radiation source: fine-focus sealed tube	2272 reflections with I > 2σ(I)
graphite	Rint = 0.045
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD profile fitting scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
Tmin = 0.956, Tmax = 0.981	l = −17→17
9175 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0621P)2 + 0.11P] where P = (Fo2 + 2Fc2)/3
4035 reflections	(Δ/σ)max < 0.001
279 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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
O4	0.6923 (3)	0.42367 (18)	0.16340 (15)	0.0676 (5)
N12	0.7836 (3)	0.3552 (2)	0.09506 (16)	0.0538 (5)
O5	0.8211 (3)	0.24401 (18)	0.09476 (15)	0.0736 (5)
N5	0.6669 (3)	0.30395 (19)	0.31822 (16)	0.0562 (5)
H5A	0.6691	0.3510	0.2770	0.067*
O6	0.8282 (3)	0.40305 (19)	0.02794 (15)	0.0719 (5)
N6	0.3306 (3)	1.0327 (2)	0.16715 (18)	0.0631 (6)
C3	0.6604 (3)	0.1553 (2)	0.44515 (18)	0.0521 (6)
H3	0.6577	0.1028	0.4885	0.063*
N1	0.2697 (3)	0.3533 (2)	0.53331 (16)	0.0581 (5)
C5	0.5298 (3)	0.3174 (2)	0.37811 (18)	0.0499 (6)
H5	0.4387	0.3755	0.3745	0.060*
C12	0.3716 (3)	0.9175 (2)	0.17583 (18)	0.0478 (5)
C6	0.3778 (3)	0.2557 (2)	0.51234 (17)	0.0466 (5)
N9	0.2512 (3)	0.8800 (2)	0.23196 (17)	0.0578 (5)
C4	0.5260 (3)	0.2439 (2)	0.44512 (17)	0.0446 (5)
C10	0.5230 (3)	0.8456 (2)	0.13170 (17)	0.0438 (5)
N2	0.1669 (3)	0.3194 (3)	0.59678 (17)	0.0641 (6)
N4	0.3414 (3)	0.1670 (2)	0.56134 (18)	0.0687 (6)
N7	0.1816 (3)	1.0644 (2)	0.2193 (2)	0.0723 (6)
C11	0.5523 (3)	0.7245 (2)	0.14313 (19)	0.0524 (6)
H11	0.4782	0.6892	0.1821	0.063*
C1	0.8009 (4)	0.2213 (3)	0.3189 (2)	0.0607 (7)
H1	0.8951	0.2166	0.2768	0.073*
N3	0.2040 (4)	0.2098 (3)	0.61492 (19)	0.0750 (7)
C2	0.7973 (4)	0.1445 (2)	0.3817 (2)	0.0577 (6)
H2	0.8872	0.0849	0.3818	0.069*
C9	0.6383 (4)	0.8947 (3)	0.0739 (2)	0.0609 (7)
H9	0.6247	0.9778	0.0664	0.073*
N10	0.6860 (3)	0.6578 (2)	0.09869 (18)	0.0673 (6)
H10A	0.7034	0.5828	0.1079	0.081*
N8	0.1327 (3)	0.9736 (2)	0.25866 (19)	0.0722 (6)
C7	0.7937 (4)	0.7011 (3)	0.0409 (2)	0.0765 (8)
H7	0.8835	0.6496	0.0096	0.092*
C8	0.7731 (4)	0.8206 (3)	0.0275 (2)	0.0752 (8)
H8	0.8490	0.8522	−0.0126	0.090*
N11	0.7936 (3)	0.4430 (2)	0.71227 (17)	0.0552 (5)
O3	0.6532 (3)	0.4772 (2)	0.75145 (17)	0.0817 (6)
O2	0.8610 (3)	0.3403 (2)	0.71981 (19)	0.0878 (6)
O1	0.8712 (3)	0.5025 (2)	0.66120 (17)	0.0809 (6)
H9A	0.236 (4)	0.802 (3)	0.248 (2)	0.069 (8)*
H2A	0.075 (4)	0.361 (3)	0.625 (2)	0.073 (9)*

	U11	U22	U33	U12	U13	U23
O4	0.0790 (12)	0.0713 (11)	0.0790 (12)	0.0375 (10)	0.0464 (10)	0.0393 (10)
N12	0.0476 (11)	0.0620 (13)	0.0548 (12)	0.0134 (10)	0.0152 (10)	0.0229 (11)
O5	0.0974 (14)	0.0641 (12)	0.0720 (12)	0.0379 (11)	0.0306 (11)	0.0287 (10)
N5	0.0711 (14)	0.0495 (11)	0.0544 (12)	0.0048 (10)	0.0232 (11)	0.0245 (10)
O6	0.0786 (13)	0.0856 (13)	0.0746 (12)	0.0245 (10)	0.0400 (11)	0.0441 (11)
N6	0.0656 (14)	0.0485 (12)	0.0753 (15)	0.0186 (10)	0.0165 (12)	0.0207 (11)
C3	0.0610 (15)	0.0476 (13)	0.0510 (14)	0.0125 (11)	0.0136 (12)	0.0212 (11)
N1	0.0603 (13)	0.0582 (12)	0.0607 (13)	0.0165 (10)	0.0265 (11)	0.0201 (10)
C5	0.0607 (15)	0.0390 (12)	0.0513 (13)	0.0091 (10)	0.0178 (12)	0.0158 (10)
C12	0.0515 (14)	0.0453 (13)	0.0438 (12)	0.0070 (10)	0.0082 (11)	0.0150 (10)
C6	0.0520 (14)	0.0427 (12)	0.0435 (12)	0.0067 (10)	0.0136 (11)	0.0134 (10)
N9	0.0576 (13)	0.0595 (13)	0.0640 (13)	0.0192 (11)	0.0237 (11)	0.0252 (11)
C4	0.0514 (13)	0.0368 (11)	0.0438 (12)	0.0064 (10)	0.0124 (11)	0.0126 (10)
C10	0.0459 (12)	0.0440 (12)	0.0420 (12)	0.0096 (10)	0.0087 (10)	0.0168 (10)
N2	0.0613 (14)	0.0750 (16)	0.0570 (13)	0.0155 (12)	0.0265 (12)	0.0182 (12)
N4	0.0868 (16)	0.0672 (14)	0.0757 (15)	0.0224 (12)	0.0410 (13)	0.0417 (12)
N7	0.0666 (15)	0.0580 (14)	0.0874 (17)	0.0235 (11)	0.0184 (13)	0.0173 (13)
C11	0.0530 (14)	0.0531 (14)	0.0543 (14)	0.0168 (11)	0.0129 (12)	0.0217 (11)
C1	0.0588 (16)	0.0592 (15)	0.0626 (16)	0.0078 (12)	0.0244 (13)	0.0165 (13)
N3	0.0845 (17)	0.0857 (17)	0.0724 (15)	0.0164 (13)	0.0395 (14)	0.0397 (13)
C2	0.0575 (15)	0.0568 (14)	0.0624 (15)	0.0190 (12)	0.0210 (13)	0.0206 (13)
C9	0.0582 (15)	0.0695 (16)	0.0628 (16)	0.0135 (13)	0.0128 (13)	0.0342 (14)
N10	0.0663 (14)	0.0599 (13)	0.0762 (15)	0.0272 (11)	0.0133 (13)	0.0234 (12)
N8	0.0632 (14)	0.0714 (15)	0.0802 (16)	0.0264 (12)	0.0262 (12)	0.0170 (13)
C7	0.0626 (18)	0.092 (2)	0.0760 (19)	0.0310 (16)	0.0234 (16)	0.0235 (17)
C8	0.0604 (17)	0.111 (2)	0.0685 (18)	0.0207 (16)	0.0271 (15)	0.0427 (18)
N11	0.0512 (12)	0.0589 (13)	0.0604 (13)	0.0121 (10)	0.0160 (11)	0.0260 (11)
O3	0.0753 (13)	0.0926 (14)	0.1060 (15)	0.0389 (11)	0.0537 (12)	0.0489 (12)
O2	0.0878 (14)	0.0793 (13)	0.1334 (18)	0.0386 (11)	0.0536 (13)	0.0643 (13)
O1	0.0872 (14)	0.0878 (13)	0.0980 (15)	0.0216 (11)	0.0476 (12)	0.0565 (12)

O4—N12	1.268 (2)	C10—C11	1.372 (3)
N12—O5	1.229 (2)	C10—C9	1.385 (3)
N12—O6	1.239 (2)	N2—N3	1.304 (3)
N5—C5	1.337 (3)	N2—H2A	0.88 (3)
N5—C1	1.338 (3)	N4—N3	1.318 (3)
N5—H5A	0.8600	N7—N8	1.288 (3)
N6—C12	1.317 (3)	C11—N10	1.324 (3)
N6—N7	1.354 (3)	C11—H11	0.9300
C3—C2	1.370 (3)	C1—C2	1.354 (3)
C3—C4	1.386 (3)	C1—H1	0.9300
C3—H3	0.9300	C2—H2	0.9300
N1—N2	1.315 (3)	C9—C8	1.377 (4)
N1—C6	1.319 (3)	C9—H9	0.9300
C5—C4	1.374 (3)	N10—C7	1.321 (3)
C5—H5	0.9300	N10—H10A	0.8600
C12—N9	1.334 (3)	C7—C8	1.354 (4)
C12—C10	1.450 (3)	C7—H7	0.9300
C6—N4	1.343 (3)	C8—H8	0.9300
C6—C4	1.469 (3)	N11—O3	1.215 (2)
N9—N8	1.345 (3)	N11—O1	1.228 (2)
N9—H9A	0.93 (2)	N11—O2	1.253 (2)
O5—N12—O6	122.0 (2)	N3—N2—H2A	118.7 (17)
O5—N12—O4	120.4 (2)	N1—N2—H2A	126.4 (17)
O6—N12—O4	117.6 (2)	N3—N4—C6	105.8 (2)
C5—N5—C1	123.6 (2)	N8—N7—N6	110.6 (2)
C5—N5—H5A	118.2	N10—C11—C10	120.0 (2)
C1—N5—H5A	118.2	N10—C11—H11	120.0
C12—N6—N7	106.2 (2)	C10—C11—H11	120.0
C2—C3—C4	120.4 (2)	N5—C1—C2	119.0 (2)
C2—C3—H3	119.8	N5—C1—H1	120.5
C4—C3—H3	119.8	C2—C1—H1	120.5
N2—N1—C6	101.2 (2)	N2—N3—N4	105.6 (2)
N5—C5—C4	118.8 (2)	C1—C2—C3	119.6 (2)
N5—C5—H5	120.6	C1—C2—H2	120.2
C4—C5—H5	120.6	C3—C2—H2	120.2
N6—C12—N9	108.2 (2)	C8—C9—C10	120.1 (2)
N6—C12—C10	125.2 (2)	C8—C9—H9	120.0
N9—C12—C10	126.7 (2)	C10—C9—H9	120.0
N1—C6—N4	112.5 (2)	C7—N10—C11	123.0 (2)
N1—C6—C4	125.0 (2)	C7—N10—H10A	118.5
N4—C6—C4	122.4 (2)	C11—N10—H10A	118.5
C12—N9—N8	108.6 (2)	N7—N8—N9	106.5 (2)
C12—N9—H9A	129.7 (16)	N10—C7—C8	119.8 (3)
N8—N9—H9A	121.5 (16)	N10—C7—H7	120.1
C5—C4—C3	118.6 (2)	C8—C7—H7	120.1
C5—C4—C6	120.5 (2)	C7—C8—C9	119.2 (3)
C3—C4—C6	120.9 (2)	C7—C8—H8	120.4
C11—C10—C9	117.9 (2)	C9—C8—H8	120.4
C11—C10—C12	120.9 (2)	O3—N11—O1	122.8 (2)
C9—C10—C12	121.2 (2)	O3—N11—O2	120.1 (2)
N3—N2—N1	114.9 (2)	O1—N11—O2	117.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9A···O2i	0.93 (2)	1.80 (3)	2.700 (3)	164 (2)
N2—H2A···O1ii	0.88 (3)	2.16 (3)	2.998 (3)	161 (2)
N2—H2A···O2ii	0.88 (3)	2.16 (3)	2.890 (3)	140 (2)
N5—H5A···O4	0.86	1.94	2.791 (3)	168
N10—H10A···O4	0.86	2.06	2.891 (3)	163
N10—H10A···O6	0.86	2.19	2.873 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9A⋯O2i	0.93 (2)	1.80 (3)	2.700 (3)	164 (2)
N2—H2A⋯O1ii	0.88 (3)	2.16 (3)	2.998 (3)	161 (2)
N2—H2A⋯O2ii	0.88 (3)	2.16 (3)	2.890 (3)	140 (2)
N5—H5A⋯O4	0.86	1.94	2.791 (3)	168
N10—H10A⋯O4	0.86	2.06	2.891 (3)	163
N10—H10A⋯O6	0.86	2.19	2.873 (3)	137

Symmetry codes: (i) ; (ii) .