2-(5-Amino-2H-tetra­zol-2-yl)acetic acid

Zhang, G.-C.; Qiao, C.-F.; Zhou, C.-S.; Xia, Z.-Q.

doi:10.1107/S1600536812014389

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1330

doi:10.1107/S1600536812014389

Open

access

2-(5-Amino-2H-tetrazol-2-yl)acetic acid

Guo-Chun Zhang,^a Cheng-Fang Qiao,^a Chun-Sheng Zhou ^a and Zheng-Qiang Xia ^b ^*

^aDepartment of Chemistry and Chemical Engineering, Shaanxi Key Laboratory of Comprehensive Utilization of Tailing Resources, Shangluo University, Shangluo 726000, Shaanxi, People's Republic of China, and ^bCollege of Chemistry and Materials Science, Northwest University, Xi'an 710069, Shaanxi, People's Republic of China
^*Correspondence e-mail: northwindy@126.com

(Received 30 March 2012; accepted 3 April 2012; online 6 April 2012)

In the title molecule, C₃H₅N₅O₂, the tetrazole ring and carboxyl group form a dihedral angle of 82.25 (14)°. In the crystal, adjacent molecules are linked through O—H⋯N, N—H⋯O and N—H⋯N hydrogen bonds into layers parallel to the bc plane.

Related literature

For background to tetrazole compounds, see: Zhao et al. (2008 ). For the use of 5-aminotetrazole-1-acetic acid in coordination chemistry, see: Li et al. (2010 ); Shen et al. (2011 ); Yang et al. (2008 ). For the crystal structures of similar compounds, see: Bryden (1956 ); Klapötke et al. (2009 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₃H₅N₅O₂
M_r = 143.12
Monoclinic, C 2/c
a = 18.381 (4) Å
b = 4.4429 (9) Å
c = 14.846 (3) Å
β = 90.850 (3)°
V = 1212.2 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 296 K
0.28 × 0.19 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.970, T_max = 0.980
3040 measured reflections
1193 independent reflections
890 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.124
S = 1.03
1193 reflections
92 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5B⋯O1ⁱ	0.86	2.36	3.080 (3)	141
N5—H5A⋯N4ⁱⁱ	0.86	2.23	3.064 (3)	163
O2—H2⋯N1ⁱⁱⁱ	0.82	1.85	2.665 (2)	172
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) -x, -y, -z; (iii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812014389/cv5277sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014389/cv5277Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812014389/cv5277Isup3.cml

checkCIF report

Comment top

In recent years, numerous tetrazole ligands were used to construct coordination compounds, which have been the subject of an intense research effort owing to their unique structures and potential applications in advanced materials (Zhao et al., 2008). However, the study of coordination compounds with disubstituted tetrazole ligands is comparatively scarce. Recently, Li et al. (2010) reported a series of lanthanide-based compounds with 5-aminotetrazole-1-acetic acid, which possesses intriguing topological structures and predominant optics performance. Inspired by this interesting work, we report here the crystal structure of a 2,5-disubstituted tetrazole compound, (5-Amino-2H-tetrazole-2-yl)acetic acid, (I).

As shown in Fig. 1, the tetrazole ring (C1/N1—N4) is essentially planar with an r.m.s. deviation of 0.008 °. The carboxyl group (O1/C3/O2) and tetrazole ring are inclined at a dihedral angle of 82.25 (14) °. All bond lengths and angles are in the normal ranges (Allen et al., 1987). The torsion angles N4–N3–C2–C3 = -80.6 (2) °, N2–N3–C2–C3 = 101.8 (2) °, O1–C3–C2–N3 = -3.6 (3) °, O2–C3–C2–N3 = 178.80 (17) °. In the crystal structure, intermolecular O—H···N, N—H···O and N—H···N hydrogen bonds (Table 1) link the molecules into a two-dimensional framework parallel to the bc plane.

Related literature top

For background to tetrazole compounds, see: Zhao et al. (2008). For the use of 5-aminotetrazole-1-acetic acid in coordination chemistry, see: Li et al. (2010); Shen et al. (2011); Yang et al. (2008). For the crystal structures of similar compounds, see: Bryden (1956); Klapötke et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

The compound was obtained commercially (Aldrich). Colourless crystals suitable for the X-ray diffraction study were obtained by slow evaporation of an ethanol/water (2:1 v/v) solution of the compound (I) at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing the atom numbering scheme and 30% probability displacement ellipsoids.

2-(5-Amino-2H-tetrazol-2-yl)acetic acid top

Crystal data top

C₃H₅N₅O₂	F(000) = 592
M_r = 143.12	D_x = 1.568 Mg m⁻³ D_m = 1.568 Mg m⁻³ D_m measured by not measured
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 734 reflections
a = 18.381 (4) Å	θ = 3.5–22.2°
b = 4.4429 (9) Å	µ = 0.13 mm⁻¹
c = 14.846 (3) Å	T = 296 K
β = 90.850 (3)°	Block, colourless
V = 1212.2 (4) Å³	0.28 × 0.19 × 0.15 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	1193 independent reflections
Radiation source: fine-focus sealed tube	890 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −22→22
T_min = 0.970, T_max = 0.980	k = −5→4
3040 measured reflections	l = −13→18

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0657P)² + 0.3572P] where P = (F_o² + 2F_c²)/3
1193 reflections	(Δ/σ)_max = 0.002
92 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₃H₅N₅O₂	V = 1212.2 (4) Å³
M_r = 143.12	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 18.381 (4) Å	µ = 0.13 mm⁻¹
b = 4.4429 (9) Å	T = 296 K
c = 14.846 (3) Å	0.28 × 0.19 × 0.15 mm
β = 90.850 (3)°

Data collection top

Bruker APEXII CCD diffractometer	1193 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	890 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.980	R_int = 0.024
3040 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
1193 reflections	Δρ_min = −0.19 e Å⁻³
92 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O2	0.17856 (8)	0.1746 (3)	0.30324 (8)	0.0527 (4)
H2	0.1626	0.2644	0.3470	0.079*
N2	0.18104 (10)	0.4658 (4)	0.01590 (11)	0.0493 (5)
N3	0.15090 (8)	0.2586 (4)	0.06465 (10)	0.0414 (4)
C3	0.14844 (11)	0.2824 (5)	0.22938 (12)	0.0426 (5)
N4	0.08911 (9)	0.1468 (4)	0.03036 (11)	0.0485 (5)
N1	0.13778 (10)	0.4994 (4)	−0.05556 (11)	0.0500 (5)
C2	0.18346 (11)	0.1507 (5)	0.14771 (12)	0.0449 (5)
H2A	0.2348	0.2010	0.1487	0.054*
H2B	0.1793	−0.0668	0.1499	0.054*
O1	0.10122 (10)	0.4680 (4)	0.22631 (10)	0.0752 (6)
C1	0.08229 (11)	0.3035 (5)	−0.04569 (13)	0.0479 (5)
N5	0.02757 (11)	0.2722 (6)	−0.10567 (13)	0.0787 (8)
H5A	−0.0064	0.1434	−0.0962	0.094*
H5B	0.0264	0.3809	−0.1536	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0661 (10)	0.0609 (10)	0.0308 (8)	0.0097 (8)	−0.0064 (6)	−0.0009 (6)
N2	0.0611 (10)	0.0547 (11)	0.0320 (9)	−0.0062 (9)	−0.0015 (7)	0.0015 (7)
N3	0.0464 (9)	0.0479 (10)	0.0300 (8)	0.0011 (7)	0.0009 (7)	−0.0019 (7)
C3	0.0479 (11)	0.0467 (12)	0.0329 (10)	0.0005 (10)	−0.0036 (8)	−0.0002 (8)
N4	0.0490 (9)	0.0622 (11)	0.0341 (9)	−0.0039 (8)	−0.0029 (7)	0.0042 (8)
N1	0.0604 (11)	0.0588 (12)	0.0309 (9)	−0.0029 (9)	−0.0027 (7)	0.0027 (7)
C2	0.0506 (11)	0.0502 (12)	0.0337 (10)	0.0068 (10)	−0.0047 (8)	0.0013 (8)
O1	0.0878 (12)	0.0979 (14)	0.0398 (9)	0.0459 (11)	−0.0038 (8)	−0.0048 (8)
C1	0.0483 (11)	0.0651 (14)	0.0303 (10)	0.0030 (10)	0.0015 (8)	0.0015 (9)
N5	0.0607 (12)	0.125 (2)	0.0503 (12)	−0.0216 (12)	−0.0165 (9)	0.0320 (12)

Geometric parameters (Å, º) top

O2—C3	1.312 (2)	N4—C1	1.331 (3)
O2—H2	0.8200	N1—C1	1.351 (3)
N2—N3	1.300 (2)	C2—H2A	0.9700
N2—N1	1.325 (2)	C2—H2B	0.9700
N3—N4	1.334 (2)	C1—N5	1.341 (2)
N3—C2	1.444 (2)	N5—H5A	0.8600
C3—O1	1.198 (2)	N5—H5B	0.8600
C3—C2	1.500 (3)

C3—O2—H2	109.5	N3—C2—H2A	109.1
N3—N2—N1	105.66 (16)	C3—C2—H2A	109.1
N2—N3—N4	114.75 (16)	N3—C2—H2B	109.1
N2—N3—C2	122.39 (16)	C3—C2—H2B	109.1
N4—N3—C2	122.81 (17)	H2A—C2—H2B	107.8
O1—C3—O2	125.45 (18)	N4—C1—N5	124.7 (2)
O1—C3—C2	123.87 (18)	N4—C1—N1	111.56 (17)
O2—C3—C2	110.64 (17)	N5—C1—N1	123.72 (19)
C1—N4—N3	101.42 (17)	C1—N5—H5A	120.0
N2—N1—C1	106.60 (16)	C1—N5—H5B	120.0
N3—C2—C3	112.53 (16)	H5A—N5—H5B	120.0

N1—N2—N3—N4	0.2 (2)	O1—C3—C2—N3	−3.6 (3)
N1—N2—N3—C2	177.93 (17)	O2—C3—C2—N3	178.80 (17)
N2—N3—N4—C1	−0.1 (2)	N3—N4—C1—N5	179.7 (2)
C2—N3—N4—C1	−177.82 (17)	N3—N4—C1—N1	0.0 (2)
N3—N2—N1—C1	−0.2 (2)	N2—N1—C1—N4	0.2 (2)
N2—N3—C2—C3	101.8 (2)	N2—N1—C1—N5	−179.6 (2)
N4—N3—C2—C3	−80.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5B···O1ⁱ	0.86	2.36	3.080 (3)	141
N5—H5A···N4ⁱⁱ	0.86	2.23	3.064 (3)	163
O2—H2···N1ⁱⁱⁱ	0.82	1.85	2.665 (2)	172

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

Experimental details

Crystal data
Chemical formula	C₃H₅N₅O₂
M_r	143.12
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	18.381 (4), 4.4429 (9), 14.846 (3)
β (°)	90.850 (3)
V (Å³)	1212.2 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.28 × 0.19 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.970, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	3040, 1193, 890
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.124, 1.03
No. of reflections	1193
No. of parameters	92
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5B···O1ⁱ	0.86	2.36	3.080 (3)	140.9
N5—H5A···N4ⁱⁱ	0.86	2.23	3.064 (3)	163.2
O2—H2···N1ⁱⁱⁱ	0.82	1.85	2.665 (2)	172.2

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

Acknowledgements

The authors gratefully acknowledge financial support from the National Science Foundation of China (grant No. 21173168) and the Science Research Plan Projects of Shaanxi Provincial Educational Department (grant No. 11 J K0578).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bryden, J. H. (1956). Acta Cryst. 9, 874–878. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Klapötke, T. M., Sabaté, C. M., Penger, A., Rusan, M. & Welch, J. M. (2009). Eur. J. Inorg. Chem. pp. 880–896. Google Scholar
Li, Q. Y., Yang, G. W., Tang, X. Y., Ma, Y. S., Yao, W., Zhou, F., Chen, J. & Zhou, H. (2010). Cryst. Growth Des. 10, 165–170. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, L., Yang, J., Ma, Y. S., Tang, X. Y., Yang, G. W., Li, Q. Y., Zhou, F., Miao, Z. F., Fei, X. W. & Huang, J. W. (2011). J. Coord. Chem. 64, 431–439. Web of Science CSD CrossRef CAS Google Scholar
Yang, G. W., Li, Q. Y., Zhou, Y., Gu, G. Q., Ma, Y. S. & Yuan, R. X. (2008). Inorg. Chem. Commun. 11, 1239–1242. Web of Science CSD CrossRef CAS Google Scholar
Zhao, H., Qu, Z. R., Ye, H. Y. & Xiong, R. G. (2008). Chem. Soc. Rev. 37, 84–100. Web of Science CrossRef PubMed Google Scholar