5-[1-(Carb­oxy­meth­yl)pyridinium-4-yl]-1,2,3,4-tetra­zol-1-ide

Feng, L.; Zhao, L.

doi:10.1107/S1600536810048403

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3310

https://doi.org/10.1107/S1600536810048403

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5-[1-(Carboxymethyl)pyridinium-4-yl]-1,2,3,4-tetrazol-1-ide

Li-ping Feng ^a ^* and Liang Zhao ^a

^aDepartment of Chemical & Environmental Engineering, Anyang Institute of Technology, Anyang 455000, People's Republic of China
^*Correspondence e-mail: ayitzhao@yahoo.com.cn

(Received 16 November 2010; accepted 20 November 2010; online 27 November 2010)

In the title compound, C₈H₇N₅O₂, the tetrazole and pyridine rings are twisted from each other by a dihedral angle of 17.97 (1)°. The zwitterionic molecules are connected by O—H⋯N hydrogen bonds into a chain parallel to [20 $[\overline{1}]$ ]. 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_r = 205.19
Monoclinic, C c
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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.082
S = 1.07
1043 reflections
137 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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⋯N3^iv	0.93	2.39	3.270 (3)	158
Symmetry codes: (i) $[x+1, -y, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) x+1, y, z.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048403/dn2625Isup2.hkl

checkCIF report

Comment top

In the past few years, there was increasing interest in the chemistry of tetrazole derivatives owing their multiple coordination modes as ligands to metal ions and for the construction of novel metal-organic frameworks (Dai & Fu 2008; Fu et al., 2009; Wen, 2008). We report here the crystal structure of the title compound, 5-(1-(carboxymethyl)pyridinium-4-yl)tetrazol-1-ide.

In the title compound (Fig.1), a carboxymethanide group was connected to the pyridine N atom, thus indicating a positive charge in the pyridine N atom. And the tetrazole ring was showing a negative charge to make the charge balance. The tetrazole and pyridine rings are twisted from each other by a dihedral angle of 17.97 (1)°. The geometric parameters of the tetrazole rings are comparable to those in related molecules (Fu et al., 2009).

In the crystal structure, the zwitterionic molecules are connected by the O—H···N hydrogen bonds, with the O···N distance of 2.646 (2)Å. This H-bonds link the zwitterionic units into a one-dimentional chain parallel to the [2 0 -1] direction (Table 1 and Fig.2). Futhermore, C-H···O and C-H···N link the chain building up a three dimensionnal network (Table 1, Fig. 2).

Related literature top

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

Experimental top

5-(1-(carboxymethyl)pyridinium-4-yl)tetrazol-1-ide (4 mmol) was dissolved in ethanol (20 ml). The solution was allowed to evaporate to obtain colourless block-shaped crystals of the title compound.

Structure description top

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

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view of the title compound showing the hydrogen bond pattern. H bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) x+1, -y, z-1/2; (ii) x-1/2, y+1/2, z; (iii) x+1/2, -y+1/2, z-1/2; (iv) x+1, y, z.]

5-[1-(Carboxymethyl)pyridinium-4-yl]-1,2,3,4-tetrazol-1-ide top

Crystal data top

C₈H₇N₅O₂	F(000) = 424
M_r = 205.19	D_x = 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

Data collection top

Rigaku Mercury2 diffractometer	1043 independent reflections
Radiation source: fine-focus sealed tube	971 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
CCD profile fitting scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
T_min = 0.910, T_max = 1.000	l = −14→14
4629 measured reflections

Refinement top

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(F_o²) + (0.0478P)² + 0.1896P] where P = (F_o² + 2F_c²)/3
1043 reflections	(Δ/σ)_max < 0.001
137 parameters	Δρ_max = 0.14 e Å⁻³
2 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₈H₇N₅O₂	V = 904.4 (3) Å³
M_r = 205.19	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 8.8094 (18) Å	µ = 0.12 mm⁻¹
b = 9.3732 (19) Å	T = 298 K
c = 11.189 (2) Å	0.10 × 0.03 × 0.03 mm
β = 101.80 (3)°

Data collection top

Rigaku Mercury2 diffractometer	1043 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	971 reflections with I > 2σ(I)
T_min = 0.910, T_max = 1.000	R_int = 0.021
4629 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	2 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.07	Δρ_max = 0.14 e Å⁻³
1043 reflections	Δρ_min = −0.20 e Å⁻³
137 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···N3^iv	0.93	2.39	3.270 (3)	158

Symmetry codes: (i) x+1, −y, z−1/2; (ii) x−1/2, y+1/2, z; (iii) x+1/2, −y+1/2, z−1/2; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₈H₇N₅O₂
M_r	205.19
Crystal system, space group	Monoclinic, Cc
Temperature (K)	298
a, b, c (Å)	8.8094 (18), 9.3732 (19), 11.189 (2)
β (°)	101.80 (3)
V (Å³)	904.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.10 × 0.03 × 0.03

Data collection
Diffractometer	Rigaku Mercury2
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.910, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4629, 1043, 971
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.082, 1.07
No. of reflections	1043
No. of parameters	137
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.20

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N4ⁱ	0.82	1.84	2.648 (3)	170.4
C1—H1···O2ⁱⁱ	0.93	2.55	3.165 (3)	124.3
C1—H1···N3ⁱⁱⁱ	0.93	2.59	3.440 (3)	151.8
C5—H5···N3^iv	0.93	2.39	3.270 (3)	157.7

Symmetry codes: (i) x+1, −y, z−1/2; (ii) x−1/2, y+1/2, z; (iii) x+1/2, −y+1/2, z−1/2; (iv) x+1, y, z.

Acknowledgements

This work was supported by a start-up grant from Henan province.

References

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