3-(1H-Tetra-zol-5-yl)benzoic acid.

The title compound, C(8)H(6)N(4)O(2), is a difunctional compound with a carboxyl-ate and a tetra-zole residue. In the crystal structure, mol-ecules are linked into two-dimensional sheets by inter-molecular N-H⋯O and O-H⋯N hydrogen bonds.

Related literature

For the applications of tetra­zoles, see: Chen & Tong (2007 ▶); Demko & Sharpless (2001 ▶). For related structures, see: Rizk et al. (2005 ▶).

Experimental

Crystal data

C8H6N4O2

M = 190.17

Monoclinic,

a = 5.2501 (10) Å

b = 16.805 (3) Å

c = 9.3290 (18) Å

β = 99.188 (3)°

V = 812.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 (2) K

0.45 × 0.14 × 0.13 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan SADABS (Sheldrick, 2000 ▶) T min = 0.949, T max = 0.985

5991 measured reflections

1583 independent reflections

1425 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.106

S = 1.07

1583 reflections

136 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808041482/bt2829sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041482/bt2829Isup2.hkl

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

C8H6N4O2	F(000) = 392
Mr = 190.17	Dx = 1.555 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 785 reflections
a = 5.2501 (10) Å	θ = 2.4–28.0°
b = 16.805 (3) Å	µ = 0.12 mm−1
c = 9.3290 (18) Å	T = 293 K
β = 99.188 (3)°	Block, colorless
V = 812.5 (3) Å3	0.45 × 0.14 × 0.13 mm
Z = 4

Bruker APX CCD diffractometer	1583 independent reflections
Radiation source: fine-focus sealed tube	1425 reflections with I > 2σ(I)
graphite	Rint = 0.018
phi and ω scan	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan SADABS (Sheldrick, 2000)	h = −6→6
Tmin = 0.949, Tmax = 0.985	k = −20→20
5991 measured reflections	l = −11→11

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0592P)2 + 0.1634P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1583 reflections	Δρmax = 0.19 e Å−3
136 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (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	0.0644 (2)	0.36005 (6)	0.68049 (12)	0.0471 (3)
O2	0.3759 (2)	0.42002 (6)	0.58687 (13)	0.0496 (3)
H2B	0.410 (4)	0.3707 (14)	0.550 (2)	0.082 (7)*
C1	0.1794 (3)	0.42040 (8)	0.65768 (15)	0.0358 (3)
C2	0.1127 (3)	0.50146 (7)	0.70380 (15)	0.0349 (3)
C3	−0.0705 (3)	0.51184 (8)	0.79498 (16)	0.0403 (4)
H3A	−0.1499	0.4680	0.8296	0.048*
C4	−0.1332 (3)	0.58797 (9)	0.83368 (16)	0.0439 (4)
H4A	−0.2539	0.5950	0.8955	0.053*
C5	−0.0189 (3)	0.65372 (8)	0.78180 (16)	0.0392 (3)
H5A	−0.0640	0.7046	0.8081	0.047*
C6	0.1642 (3)	0.64386 (7)	0.68994 (14)	0.0338 (3)
C7	0.2301 (2)	0.56732 (8)	0.65297 (14)	0.0356 (3)
H7A	0.3544	0.5602	0.5934	0.043*
C8	0.2910 (3)	0.71171 (7)	0.63149 (14)	0.0338 (3)
N1	0.2597 (2)	0.78846 (7)	0.66034 (13)	0.0402 (3)
N2	0.4101 (3)	0.83282 (7)	0.58804 (14)	0.0453 (3)
N3	0.5310 (3)	0.78398 (7)	0.51637 (14)	0.0445 (3)
N4	0.4608 (2)	0.70804 (7)	0.54077 (13)	0.0394 (3)
H1A	0.147 (4)	0.8129 (12)	0.716 (2)	0.067 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0573 (7)	0.0296 (5)	0.0618 (7)	−0.0056 (4)	0.0317 (5)	0.0017 (4)
O2	0.0616 (7)	0.0266 (5)	0.0718 (7)	−0.0021 (4)	0.0446 (6)	−0.0037 (5)
C1	0.0416 (7)	0.0290 (7)	0.0408 (7)	−0.0007 (5)	0.0188 (6)	0.0037 (5)
C2	0.0379 (7)	0.0299 (7)	0.0400 (7)	0.0007 (5)	0.0158 (6)	0.0010 (5)
C3	0.0448 (8)	0.0328 (7)	0.0485 (8)	−0.0023 (6)	0.0231 (6)	0.0013 (6)
C4	0.0468 (8)	0.0408 (8)	0.0510 (8)	0.0015 (6)	0.0285 (7)	−0.0021 (6)
C5	0.0434 (8)	0.0305 (7)	0.0474 (8)	0.0036 (5)	0.0188 (6)	−0.0048 (6)
C6	0.0374 (7)	0.0285 (7)	0.0380 (7)	−0.0004 (5)	0.0133 (5)	−0.0002 (5)
C7	0.0394 (7)	0.0311 (7)	0.0406 (7)	0.0002 (5)	0.0195 (6)	0.0003 (5)
C8	0.0383 (7)	0.0266 (6)	0.0388 (7)	0.0026 (5)	0.0131 (5)	−0.0021 (5)
N1	0.0498 (7)	0.0263 (6)	0.0496 (7)	0.0012 (5)	0.0238 (6)	−0.0017 (5)
N2	0.0564 (8)	0.0290 (6)	0.0559 (8)	−0.0022 (5)	0.0257 (6)	0.0001 (5)
N3	0.0537 (7)	0.0293 (6)	0.0562 (8)	−0.0026 (5)	0.0260 (6)	0.0005 (5)
N4	0.0470 (7)	0.0263 (6)	0.0504 (7)	−0.0010 (5)	0.0247 (5)	−0.0010 (5)

O1—C1	1.2163 (16)	C5—H5A	0.9300
O2—C1	1.3112 (16)	C6—C7	1.3898 (18)
O2—H2B	0.93 (2)	C6—C8	1.4684 (18)
C1—C2	1.4871 (18)	C7—H7A	0.9300
C2—C7	1.3868 (18)	C8—N4	1.3254 (17)
C2—C3	1.3927 (19)	C8—N1	1.3331 (17)
C3—C4	1.3833 (19)	N1—N2	1.3430 (16)
C3—H3A	0.9300	N1—H1A	0.94 (2)
C4—C5	1.381 (2)	N2—N3	1.2882 (17)
C4—H4A	0.9300	N3—N4	1.3576 (16)
C5—C6	1.3961 (18)
C1—O2—H2B	114.1 (14)	C7—C6—C5	119.03 (12)
O1—C1—O2	122.47 (12)	C7—C6—C8	118.74 (11)
O1—C1—C2	124.52 (12)	C5—C6—C8	122.22 (12)
O2—C1—C2	113.01 (11)	C2—C7—C6	120.79 (12)
C7—C2—C3	119.79 (12)	C2—C7—H7A	119.6
C7—C2—C1	119.61 (11)	C6—C7—H7A	119.6
C3—C2—C1	120.59 (11)	N4—C8—N1	106.91 (11)
C4—C3—C2	119.44 (12)	N4—C8—C6	126.31 (11)
C4—C3—H3A	120.3	N1—C8—C6	126.77 (12)
C2—C3—H3A	120.3	C8—N1—N2	109.54 (11)
C5—C4—C3	120.91 (12)	C8—N1—H1A	129.9 (12)
C5—C4—H4A	119.5	N2—N1—H1A	120.5 (12)
C3—C4—H4A	119.5	N3—N2—N1	106.56 (11)
C4—C5—C6	120.02 (12)	N2—N3—N4	110.02 (11)
C4—C5—H5A	120.0	C8—N4—N3	106.96 (10)
C6—C5—H5A	120.0

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···N4i	0.93 (2)	1.76 (2)	2.6664 (15)	164 (2)
N1—H1A···O1ii	0.94 (2)	1.77 (2)	2.7118 (16)	179.1 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯N4i	0.93 (2)	1.76 (2)	2.6664 (15)	164 (2)
N1—H1A⋯O1ii	0.94 (2)	1.77 (2)	2.7118 (16)	179.1 (19)

Symmetry codes: (i) ; (ii) .