4-(1H-Tetra-zol-5-yl)benzoic acid monohydrate.

The asymmetric unit of the title compound, C(8)H(6)N(4)O(2)·H(2)O, consists of one 4-(1H-tetra-zol-5-yl)benzoic acid mol-ecule and one water mol-ecule. Hydrogen-bonding and π-π stacking (centroid-centroid distance between tetra-zole and benzene rings = 3.78 Å) inter-actions link the mol-ecules into a three-dimensional network.

Related literature

For general background, see: James et al. (2003 ▶); Kitagawa & Matsuda (2007 ▶); Maspoch et al. (2007 ▶); Pan et al. (2006 ▶); Li et al. (2007 ▶). For related tetra­zole ligands, see: Demko et al. (2001 ▶).

Experimental

Crystal data

C8H6N4O2·H2O

M = 208.18

Monoclinic,

a = 4.914 (2) Å

b = 5.219 (2) Å

c = 34.720 (13) Å

β = 91.00 (3)°

V = 890.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 (2) K

0.20 × 0.10 × 0.10 mm

Data collection

Rigaku AFC-7R diffractometer

Absorption correction: ψ scan (Psi in ; Rigaku 2002 ▶) T min = 0.927, T max = 1.000 (expected range = 0.917–0.988)

3386 measured reflections

1576 independent reflections

1270 reflections with I > 2σ(I)

R int = 0.028

3 standard reflections every 200 reflections intensity decay: 0.3%

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.095

S = 1.01

1576 reflections

148 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.29 e Å−3

Data collection: WinAFC Diffractometer Control Software (Rigaku, 2002 ▶); cell refinement: WinAFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019053/sj2513sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019053/sj2513Isup2.hkl

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

C8H6N4O2·H2O	F000 = 432
Mr = 208.18	Dx = 1.553 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 20 reflections
a = 4.914 (2) Å	θ = 12–30º
b = 5.219 (2) Å	µ = 0.12 mm−1
c = 34.720 (13) Å	T = 293 (2) K
β = 91.00 (3)º	Block, colorless
V = 890.4 (6) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Rigaku AFC-7R diffractometer	Rint = 0.028
Radiation source: rotating-anode generator	θmax = 25.0º
Monochromator: graphite	θmin = 3.5º
T = 293(2) K	h = −1→5
ω–2θ scans	k = −6→6
Absorption correction: ψ scan(Psi in WinAFC Diffractometer Control Software; Rigaku 2002)	l = −41→41
Tmin = 0.928, Tmax = 1.000	3 standard reflections
3386 measured reflections	every 200 reflections
1576 independent reflections	intensity decay: 0.3%
1270 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0403P)2 + 0.366P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1576 reflections	Δρmax = 0.17 e Å−3
148 parameters	Δρmin = −0.29 e Å−3
4 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
O1W	1.3075 (3)	1.2115 (3)	0.22404 (4)	0.0510 (4)
H1WA	1.400 (4)	1.292 (4)	0.2414 (5)	0.061*
H1WB	1.175 (3)	1.304 (4)	0.2153 (6)	0.061*
O1	0.6331 (3)	1.1354 (3)	0.04240 (4)	0.0456 (4)
H1	0.509 (4)	1.157 (6)	0.0242 (6)	0.100*
O2	0.7482 (3)	0.7840 (3)	0.00986 (3)	0.0453 (4)
N1	1.6033 (3)	0.8366 (3)	0.18939 (4)	0.0363 (4)
H2	1.514 (4)	0.965 (3)	0.1990 (6)	0.068*
N2	1.8032 (3)	0.7255 (3)	0.21010 (4)	0.0429 (4)
N3	1.8788 (3)	0.5272 (3)	0.19041 (4)	0.0439 (4)
N4	1.7318 (3)	0.5062 (3)	0.15713 (4)	0.0396 (4)
C1	0.9801 (3)	0.8752 (3)	0.06869 (4)	0.0301 (4)
C2	1.1494 (4)	0.6629 (3)	0.06537 (5)	0.0345 (4)
H2A	1.1350	0.5576	0.0438	0.041*
C3	1.3393 (4)	0.6083 (3)	0.09416 (5)	0.0338 (4)
H3A	1.4531	0.4669	0.0918	0.041*
C4	1.3602 (3)	0.7647 (3)	0.12651 (4)	0.0289 (4)
C5	1.1923 (4)	0.9778 (3)	0.12961 (5)	0.0340 (4)
H5A	1.2076	1.0839	0.1511	0.041*
C6	1.0034 (3)	1.0320 (3)	0.10098 (5)	0.0332 (4)
H6A	0.8908	1.1742	0.1033	0.040*
C7	0.7755 (3)	0.9317 (3)	0.03801 (5)	0.0319 (4)
C8	1.5608 (3)	0.7022 (3)	0.15704 (4)	0.0297 (4)

	U11	U22	U33	U12	U13	U23
O1W	0.0586 (9)	0.0478 (9)	0.0459 (8)	0.0216 (7)	−0.0217 (6)	−0.0168 (6)
O1	0.0509 (8)	0.0439 (8)	0.0414 (7)	0.0187 (7)	−0.0173 (6)	−0.0079 (6)
O2	0.0510 (8)	0.0496 (8)	0.0348 (7)	0.0147 (7)	−0.0156 (6)	−0.0130 (6)
N1	0.0399 (9)	0.0372 (9)	0.0313 (8)	0.0110 (7)	−0.0114 (6)	−0.0040 (6)
N2	0.0458 (9)	0.0444 (9)	0.0380 (8)	0.0125 (8)	−0.0152 (7)	−0.0023 (7)
N3	0.0463 (9)	0.0443 (9)	0.0407 (8)	0.0143 (8)	−0.0138 (7)	−0.0013 (7)
N4	0.0430 (9)	0.0381 (9)	0.0374 (8)	0.0117 (7)	−0.0102 (7)	−0.0024 (7)
C1	0.0313 (9)	0.0303 (9)	0.0286 (8)	0.0010 (7)	−0.0027 (7)	−0.0002 (7)
C2	0.0396 (10)	0.0334 (10)	0.0302 (9)	0.0043 (8)	−0.0055 (7)	−0.0071 (7)
C3	0.0350 (9)	0.0318 (9)	0.0346 (9)	0.0077 (8)	−0.0052 (7)	−0.0029 (7)
C4	0.0289 (8)	0.0300 (9)	0.0277 (8)	0.0008 (7)	−0.0035 (7)	0.0016 (7)
C5	0.0399 (10)	0.0323 (9)	0.0294 (9)	0.0050 (8)	−0.0070 (7)	−0.0064 (7)
C6	0.0360 (9)	0.0297 (9)	0.0337 (9)	0.0080 (8)	−0.0052 (7)	−0.0027 (7)
C7	0.0333 (9)	0.0326 (9)	0.0296 (9)	0.0035 (8)	−0.0031 (7)	−0.0011 (7)
C8	0.0322 (9)	0.0285 (9)	0.0284 (8)	0.0020 (8)	−0.0029 (7)	0.0010 (7)

O1W—H1WA	0.858 (10)	C1—C2	1.392 (2)
O1W—H1WB	0.859 (10)	C1—C7	1.482 (2)
O1—C7	1.283 (2)	C2—C3	1.385 (2)
O1—H1	0.877 (10)	C2—H2A	0.9300
O2—C7	1.250 (2)	C3—C4	1.391 (2)
N1—C8	1.337 (2)	C3—H3A	0.9300
N1—N2	1.339 (2)	C4—C5	1.390 (2)
N1—H2	0.872 (10)	C4—C8	1.471 (2)
N2—N3	1.298 (2)	C5—C6	1.378 (2)
N3—N4	1.356 (2)	C5—H5A	0.9300
N4—C8	1.324 (2)	C6—H6A	0.9300
C1—C6	1.391 (2)
H1WA—O1W—H1WB	111 (2)	C4—C3—H3A	120.0
C7—O1—H1	113 (2)	C5—C4—C3	119.78 (15)
C8—N1—N2	109.02 (14)	C5—C4—C8	120.84 (15)
C8—N1—H2	130.9 (16)	C3—C4—C8	119.38 (15)
N2—N1—H2	119.7 (15)	C6—C5—C4	120.14 (15)
N3—N2—N1	106.08 (14)	C6—C5—H5A	119.9
N2—N3—N4	111.08 (14)	C4—C5—H5A	119.9
C8—N4—N3	105.55 (14)	C5—C6—C1	120.35 (16)
C6—C1—C2	119.63 (15)	C5—C6—H6A	119.8
C6—C1—C7	120.49 (15)	C1—C6—H6A	119.8
C2—C1—C7	119.88 (15)	O2—C7—O1	123.55 (15)
C3—C2—C1	120.02 (16)	O2—C7—C1	120.08 (15)
C3—C2—H2A	120.0	O1—C7—C1	116.37 (14)
C1—C2—H2A	120.0	N4—C8—N1	108.27 (14)
C2—C3—C4	120.08 (16)	N4—C8—C4	126.17 (15)
C2—C3—H3A	120.0	N1—C8—C4	125.55 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.877 (10)	1.744 (10)	2.620 (2)	176 (3)
O1W—H1WA···N2ii	0.858 (10)	2.234 (16)	2.957 (2)	142 (2)
O1W—H1WB···N3iii	0.859 (10)	2.046 (10)	2.903 (2)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.877 (10)	1.744 (10)	2.620 (2)	176 (3)
O1W—H1WA⋯N2ii	0.858 (10)	2.234 (16)	2.957 (2)	142 (2)
O1W—H1WB⋯N3iii	0.859 (10)	2.046 (10)	2.903 (2)	175 (2)

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