2-(1H-Tetra-zol-1-yl)acetic acid monohydrate.

The crystal structure of the title compound, C(3)H(4)N(4)O(2)·H(2)O, exhibits O-H⋯O and O-H⋯N hydrogen bonds, which lead to the formation of a two-dimensional network parallel to the bc plane. The dihedral angle between the ring and the carboxylic acid group is 84.6 (14)°.

Related literature

For the use of 2-(1H-tetra­zol-1-yl) acetic acid as a pharmaceutical inter­mediate, see: Gunnlaugsson & Stomeo (2007 ▶). For its coordination properties, see: Ghosh & Bharadwaj (2004 ▶). For the synthesis, see: Jústiz et al. (1997 ▶).

Experimental

Crystal data

C3H4N4O2·H2O

M = 146.12

Orthorhombic,

a = 12.618 (3) Å

b = 5.1871 (10) Å

c = 9.874 (2) Å

V = 646.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.26 × 0.23 × 0.19 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.965, T max = 0.983

6216 measured reflections

786 independent reflections

715 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.069

S = 1.17

786 reflections

103 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.11 e Å−3

Δρmin = −0.12 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: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033090/fy2060sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033090/fy2060Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033090/fy2060Isup3.cml

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

C3H4N4O2·H2O	F(000) = 304
Mr = 146.12	Dx = 1.502 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6216 reflections
a = 12.618 (3) Å	θ = 3.2–27.5°
b = 5.1871 (10) Å	µ = 0.13 mm−1
c = 9.874 (2) Å	T = 293 K
V = 646.2 (2) Å3	Needle, pale yellow
Z = 4	0.26 × 0.23 × 0.19 mm

Rigaku SCXmini diffractometer	786 independent reflections
Radiation source: fine-focus sealed tube	715 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −16→16
Tmin = 0.965, Tmax = 0.983	k = −6→6
6216 measured reflections	l = −12→12

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.029P)2 + 0.0792P] where P = (Fo2 + 2Fc2)/3
786 reflections	(Δ/σ)max < 0.001
103 parameters	Δρmax = 0.11 e Å−3
1 restraint	Δρmin = −0.12 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
O1	0.38513 (14)	0.5364 (3)	1.01953 (17)	0.0450 (4)
O2	0.30421 (14)	0.8326 (3)	0.89450 (17)	0.0525 (5)
N2	0.37640 (16)	0.8301 (4)	0.4743 (2)	0.0436 (5)
C5	0.36860 (19)	0.6540 (4)	0.5678 (2)	0.0381 (5)
H5A	0.3281	0.5047	0.5614	0.046*
N4	0.47431 (18)	0.9471 (4)	0.6448 (2)	0.0497 (5)
C7	0.37025 (18)	0.6679 (4)	0.9087 (2)	0.0358 (5)
N1	0.44272 (18)	1.0105 (4)	0.5252 (2)	0.0527 (6)
N3	0.42748 (14)	0.7205 (3)	0.67377 (18)	0.0334 (4)
C6	0.44751 (19)	0.5888 (4)	0.8003 (2)	0.0379 (5)
H6A	0.5190	0.6270	0.8302	0.046*
H6B	0.4424	0.4042	0.7860	0.046*
O3	0.27445 (17)	0.7053 (4)	0.22354 (17)	0.0509 (5)
H1A	0.344 (3)	0.595 (6)	1.086 (4)	0.079 (11)*
H3A	0.246 (2)	0.600 (6)	0.263 (4)	0.062 (10)*
H3B	0.310 (3)	0.789 (6)	0.279 (4)	0.062 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0495 (9)	0.0525 (10)	0.0330 (9)	0.0046 (8)	−0.0002 (8)	0.0146 (8)
O2	0.0605 (10)	0.0645 (11)	0.0327 (9)	0.0259 (9)	0.0079 (8)	0.0131 (9)
N2	0.0554 (12)	0.0453 (11)	0.0303 (9)	−0.0005 (9)	0.0026 (9)	0.0036 (9)
C5	0.0438 (14)	0.0403 (12)	0.0303 (11)	−0.0033 (9)	0.0011 (9)	−0.0052 (9)
N4	0.0678 (14)	0.0421 (11)	0.0393 (11)	−0.0149 (10)	0.0003 (11)	−0.0023 (9)
C7	0.0409 (12)	0.0368 (11)	0.0298 (11)	−0.0010 (10)	−0.0039 (9)	0.0036 (10)
N1	0.0729 (14)	0.0454 (11)	0.0396 (12)	−0.0118 (10)	0.0050 (12)	0.0042 (10)
N3	0.0402 (9)	0.0325 (9)	0.0276 (8)	0.0000 (8)	0.0031 (8)	−0.0036 (7)
C6	0.0446 (12)	0.0366 (11)	0.0326 (11)	0.0070 (11)	−0.0046 (10)	−0.0011 (9)
O3	0.0612 (11)	0.0625 (12)	0.0289 (9)	−0.0116 (10)	−0.0018 (8)	0.0107 (9)

O1—C7	1.303 (3)	N4—N3	1.346 (3)
O1—H1A	0.89 (4)	C7—C6	1.505 (3)
O2—C7	1.202 (3)	N3—C6	1.446 (3)
N2—C5	1.303 (3)	C6—H6A	0.9700
N2—N1	1.352 (3)	C6—H6B	0.9700
C5—N3	1.329 (3)	O3—H3A	0.76 (3)
C5—H5A	0.9300	O3—H3B	0.83 (4)
N4—N1	1.289 (3)
C7—O1—H1A	111 (2)	C5—N3—N4	107.74 (19)
C5—N2—N1	105.6 (2)	C5—N3—C6	130.92 (19)
N2—C5—N3	109.49 (19)	N4—N3—C6	121.31 (19)
N2—C5—H5A	125.3	N3—C6—C7	111.87 (17)
N3—C5—H5A	125.3	N3—C6—H6A	109.2
N1—N4—N3	106.37 (19)	C7—C6—H6A	109.2
O2—C7—O1	124.8 (2)	N3—C6—H6B	109.2
O2—C7—C6	124.0 (2)	C7—C6—H6B	109.2
O1—C7—C6	111.19 (19)	H6A—C6—H6B	107.9
N4—N1—N2	110.82 (19)	H3A—O3—H3B	107 (3)
N1—N2—C5—N3	0.1 (3)	N1—N4—N3—C6	178.50 (19)
N3—N4—N1—N2	−0.3 (3)	C5—N3—C6—C7	−92.1 (3)
C5—N2—N1—N4	0.1 (3)	N4—N3—C6—C7	90.3 (3)
N2—C5—N3—N4	−0.3 (3)	O2—C7—C6—N3	−4.4 (3)
N2—C5—N3—C6	−178.2 (2)	O1—C7—C6—N3	176.12 (18)
N1—N4—N3—C5	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···N2	0.83 (4)	2.11 (4)	2.864 (3)	150 (3)
O1—H1A···O3i	0.89 (4)	1.72 (4)	2.603 (3)	175 (4)
O3—H3A···O2ii	0.76 (3)	2.00 (3)	2.752 (3)	168 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯N2	0.83 (4)	2.11 (4)	2.864 (3)	150 (3)
O1—H1A⋯O3i	0.89 (4)	1.72 (4)	2.603 (3)	175 (4)
O3—H3A⋯O2ii	0.76 (3)	2.00 (3)	2.752 (3)	168 (3)

Symmetry codes: (i) ; (ii) .