5-[1-(Carb-oxy-meth-yl)pyridinium-4-yl]-1,2,3,4-tetra-zol-1-ide.

In the title compound, C(8)H(7)N(5)O(2), the tetra-zole and pyridine rings are twisted from each other by a dihedral angle of 17.97 (1)°. The zwitterionic mol-ecules are connected by O-H⋯N hydrogen bonds into a chain parallel to [20]. Further C-H⋯O and C-H⋯N hydrogen bonds link the chains, building up a three-dimensional network.

Related literature

For the chemisty of tetra­zoles and for related structures, see: Fu et al. (2009 ▶); Wen (2008 ▶); Dai & Fu (2008 ▶).

Experimental

Crystal data

C8H7N5O2

M = 205.19

Monoclinic,

a = 8.8094 (18) Å

b = 9.3732 (19) Å

c = 11.189 (2) Å

β = 101.80 (3)°

V = 904.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 298 K

0.10 × 0.03 × 0.03 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.910, T max = 1.000

4629 measured reflections

1043 independent reflections

971 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.082

S = 1.07

1043 reflections

137 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.20 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: XP in SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048403/dn2625sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048403/dn2625Isup2.hkl

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

C8H7N5O2	F(000) = 424
Mr = 205.19	Dx = 1.507 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2059 reflections
a = 8.8094 (18) Å	θ = 3.2–27.5°
b = 9.3732 (19) Å	µ = 0.12 mm−1
c = 11.189 (2) Å	T = 298 K
β = 101.80 (3)°	Block, colourless
V = 904.4 (3) Å3	0.10 × 0.03 × 0.03 mm
Z = 4

Rigaku Mercury2 diffractometer	1043 independent reflections
Radiation source: fine-focus sealed tube	971 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
CCD profile fitting scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
Tmin = 0.910, Tmax = 1.000	l = −14→14
4629 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0478P)2 + 0.1896P] where P = (Fo2 + 2Fc2)/3
1043 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.14 e Å−3
2 restraints	Δρmin = −0.20 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	1.1510 (2)	0.22028 (18)	0.28067 (17)	0.0424 (4)
H1A	1.1988	0.1581	0.2523	0.064*
O2	0.9872 (2)	0.04264 (18)	0.30239 (18)	0.0473 (4)
N1	0.83175 (19)	0.21616 (19)	0.43834 (16)	0.0302 (4)
N2	0.3137 (2)	0.1524 (3)	0.5601 (2)	0.0498 (6)
N3	0.2244 (2)	0.0761 (3)	0.6185 (2)	0.0488 (6)
N4	0.2990 (2)	−0.0370 (2)	0.66513 (19)	0.0411 (5)
N5	0.4411 (2)	−0.0394 (2)	0.6403 (2)	0.0414 (5)
C1	0.6906 (3)	0.2695 (3)	0.3907 (2)	0.0374 (5)
H1	0.6795	0.3366	0.3283	0.045*
C2	0.5627 (3)	0.2256 (3)	0.4332 (2)	0.0383 (5)
H2	0.4658	0.2645	0.4011	0.046*
C3	0.5786 (2)	0.1231 (2)	0.5242 (2)	0.0306 (4)
C4	0.7249 (3)	0.0675 (2)	0.5702 (2)	0.0371 (5)
H4	0.7380	−0.0023	0.6304	0.045*
C5	0.8499 (3)	0.1156 (2)	0.5265 (2)	0.0375 (5)
H5	0.9480	0.0788	0.5578	0.045*
C6	0.4446 (2)	0.0779 (2)	0.57437 (19)	0.0320 (5)
C7	0.9702 (2)	0.2699 (2)	0.3979 (2)	0.0339 (5)
H7A	1.0494	0.2934	0.4690	0.041*
H7B	0.9435	0.3567	0.3511	0.041*
C8	1.0352 (2)	0.1622 (2)	0.32033 (19)	0.0308 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0384 (8)	0.0479 (9)	0.0486 (9)	0.0017 (7)	0.0268 (8)	0.0014 (8)
O2	0.0452 (10)	0.0420 (9)	0.0610 (11)	−0.0036 (8)	0.0258 (9)	−0.0095 (8)
N1	0.0251 (9)	0.0346 (9)	0.0351 (9)	0.0004 (7)	0.0156 (7)	0.0006 (7)
N2	0.0292 (9)	0.0692 (14)	0.0553 (13)	0.0078 (10)	0.0184 (9)	0.0190 (11)
N3	0.0272 (9)	0.0736 (16)	0.0495 (11)	−0.0015 (10)	0.0168 (8)	0.0095 (11)
N4	0.0321 (9)	0.0537 (12)	0.0429 (10)	−0.0090 (9)	0.0202 (8)	−0.0053 (9)
N5	0.0333 (10)	0.0468 (11)	0.0504 (11)	−0.0008 (8)	0.0232 (9)	0.0039 (9)
C1	0.0328 (11)	0.0421 (12)	0.0406 (11)	0.0048 (9)	0.0152 (9)	0.0104 (10)
C2	0.0256 (10)	0.0484 (13)	0.0431 (13)	0.0047 (9)	0.0121 (9)	0.0081 (10)
C3	0.0247 (9)	0.0385 (11)	0.0312 (10)	−0.0004 (8)	0.0116 (8)	−0.0031 (8)
C4	0.0295 (10)	0.0417 (11)	0.0434 (12)	0.0028 (9)	0.0150 (9)	0.0125 (11)
C5	0.0246 (9)	0.0462 (12)	0.0438 (12)	0.0072 (9)	0.0119 (9)	0.0103 (10)
C6	0.0276 (10)	0.0389 (11)	0.0320 (10)	−0.0029 (8)	0.0117 (9)	−0.0016 (8)
C7	0.0296 (11)	0.0359 (11)	0.0419 (12)	−0.0011 (8)	0.0205 (9)	0.0005 (9)
C8	0.0284 (9)	0.0334 (10)	0.0331 (10)	0.0035 (8)	0.0120 (8)	0.0014 (9)

O1—C8	1.311 (3)	C1—H1	0.9300
O1—H1A	0.8200	C2—C3	1.386 (3)
O2—C8	1.200 (3)	C2—H2	0.9300
N1—C1	1.345 (3)	C3—C4	1.388 (3)
N1—C5	1.350 (3)	C3—C6	1.469 (3)
N1—C7	1.474 (3)	C4—C5	1.370 (3)
N2—N3	1.329 (3)	C4—H4	0.9300
N2—C6	1.330 (3)	C5—H5	0.9300
N3—N4	1.299 (3)	C7—C8	1.517 (3)
N4—N5	1.337 (3)	C7—H7A	0.9700
N5—C6	1.328 (3)	C7—H7B	0.9700
C1—C2	1.373 (3)
C8—O1—H1A	109.5	C5—C4—H4	120.1
C1—N1—C5	120.71 (18)	C3—C4—H4	120.1
C1—N1—C7	120.49 (18)	N1—C5—C4	120.5 (2)
C5—N1—C7	118.77 (18)	N1—C5—H5	119.8
N3—N2—C6	104.1 (2)	C4—C5—H5	119.8
N4—N3—N2	109.6 (2)	N5—C6—N2	112.5 (2)
N3—N4—N5	110.4 (2)	N5—C6—C3	124.28 (19)
C6—N5—N4	103.3 (2)	N2—C6—C3	123.2 (2)
N1—C1—C2	120.6 (2)	N1—C7—C8	112.40 (17)
N1—C1—H1	119.7	N1—C7—H7A	109.1
C2—C1—H1	119.7	C8—C7—H7A	109.1
C1—C2—C3	119.7 (2)	N1—C7—H7B	109.1
C1—C2—H2	120.2	C8—C7—H7B	109.1
C3—C2—H2	120.2	H7A—C7—H7B	107.9
C2—C3—C4	118.6 (2)	O2—C8—O1	127.1 (2)
C2—C3—C6	120.81 (19)	O2—C8—C7	123.7 (2)
C4—C3—C6	120.52 (19)	O1—C8—C7	109.16 (17)
C5—C4—C3	119.8 (2)
C6—N2—N3—N4	0.3 (3)	N4—N5—C6—N2	1.3 (3)
N2—N3—N4—N5	0.5 (3)	N4—N5—C6—C3	−179.9 (2)
N3—N4—N5—C6	−1.0 (3)	N3—N2—C6—N5	−1.0 (3)
C5—N1—C1—C2	1.9 (4)	N3—N2—C6—C3	−179.9 (2)
C7—N1—C1—C2	−176.2 (2)	C2—C3—C6—N5	164.3 (2)
N1—C1—C2—C3	−1.5 (4)	C4—C3—C6—N5	−17.9 (3)
C1—C2—C3—C4	0.1 (3)	C2—C3—C6—N2	−17.0 (3)
C1—C2—C3—C6	177.9 (2)	C4—C3—C6—N2	160.8 (2)
C2—C3—C4—C5	0.9 (4)	C1—N1—C7—C8	−108.5 (2)
C6—C3—C4—C5	−176.9 (2)	C5—N1—C7—C8	73.4 (3)
C1—N1—C5—C4	−0.9 (4)	N1—C7—C8—O2	−5.8 (3)
C7—N1—C5—C4	177.2 (2)	N1—C7—C8—O1	175.68 (18)
C3—C4—C5—N1	−0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N4i	0.82	1.84	2.648 (3)	170
C1—H1···O2ii	0.93	2.55	3.165 (3)	124
C1—H1···N3iii	0.93	2.59	3.440 (3)	152
C5—H5···N3iv	0.93	2.39	3.270 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N4i	0.82	1.84	2.648 (3)	170
C1—H1⋯O2ii	0.93	2.55	3.165 (3)	124
C1—H1⋯N3iii	0.93	2.59	3.440 (3)	152
C5—H5⋯N3iv	0.93	2.39	3.270 (3)	158

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