4-(Imidazol-1-yl)benzoic acid.

In the title mol-ecule, C(10)H(8)N(2)O(2), the imidazole and benzene rings form a dihedral angle of 14.5 (1)°. In the crystal, inter-molecular O-H⋯N hydrogen bonds link the mol-ecules into chains extending in [01], which are further linked into sheets parallel to (102) through weak C-H⋯O inter-actions.

Related literature

The crystal structures of the Cd and Co complexes with the title mol­ecule were described by Gao et al. (2009 ▶) and Zhang et al. (2007 ▶), respectively.

Experimental

Crystal data

C10H8N2O2

M = 188.18

Monoclinic,

a = 4.1443 (11) Å

b = 6.6561 (19) Å

c = 15.706 (4) Å

β = 101.023 (7)°

V = 425.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.969, T max = 0.979

2483 measured reflections

782 independent reflections

626 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.104

S = 0.71

782 reflections

128 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536811003345/cv5031sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003345/cv5031Isup2.hkl

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

C10H8N2O2	F(000) = 196
Mr = 188.18	Dx = 1.470 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
a = 4.1443 (11) Å	Cell parameters from 553 reflections
b = 6.6561 (19) Å	θ = 2.6–21.0°
c = 15.706 (4) Å	µ = 0.11 mm−1
β = 101.023 (7)°	T = 296 K
V = 425.3 (2) Å3	Prism, yellow
Z = 2	0.30 × 0.20 × 0.20 mm

Bruker SMART CCD diffractometer	782 independent reflections
Radiation source: fine-focus sealed tube	626 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −3→4
Tmin = 0.969, Tmax = 0.979	k = −7→8
2483 measured reflections	l = −18→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 0.71	w = 1/[σ2(Fo2) + (0.0601P)2 + 0.4878P] where P = (Fo2 + 2Fc2)/3
782 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.14 e Å−3
2 restraints	Δρmin = −0.17 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	0.4877 (9)	−0.2462 (5)	0.4370 (2)	0.0588 (9)
H1	0.4273	−0.2969	0.4789	0.088*
O2	0.5637 (9)	0.0207 (5)	0.52362 (19)	0.0599 (10)
N1	1.0752 (8)	0.3543 (5)	0.1902 (2)	0.0415 (9)
C9	1.2725 (12)	0.5824 (7)	0.1140 (3)	0.0569 (13)
H9	1.3408	0.7049	0.0952	0.068*
C2	0.7016 (11)	0.0470 (6)	0.3847 (3)	0.0413 (10)
C4	0.8260 (11)	0.0591 (6)	0.2410 (3)	0.0444 (11)
H4	0.8267	−0.0025	0.1878	0.053*
C7	0.8116 (11)	0.2437 (7)	0.3973 (3)	0.0499 (11)
H7	0.8012	0.3079	0.4493	0.060*
C3	0.7080 (10)	−0.0435 (7)	0.3054 (3)	0.0462 (11)
H3	0.6322	−0.1745	0.2954	0.055*
N2	1.2859 (9)	0.4028 (6)	0.0725 (2)	0.0518 (10)
C6	0.9360 (11)	0.3462 (7)	0.3342 (3)	0.0491 (12)
H6	1.0147	0.4766	0.3443	0.059*
C1	0.5766 (11)	−0.0580 (6)	0.4551 (3)	0.0465 (11)
C5	0.9428 (9)	0.2532 (6)	0.2556 (3)	0.0399 (10)
C8	1.1662 (11)	0.2706 (7)	0.1202 (2)	0.0466 (11)
H8	1.1463	0.1343	0.1071	0.056*
C10	1.1460 (13)	0.5559 (7)	0.1859 (3)	0.0548 (12)
H10	1.1128	0.6547	0.2252	0.066*

	U11	U22	U33	U12	U13	U23
O1	0.088 (3)	0.047 (2)	0.0476 (17)	−0.0050 (18)	0.0288 (17)	−0.0015 (14)
O2	0.094 (3)	0.049 (2)	0.0417 (17)	0.0028 (19)	0.0252 (18)	−0.0047 (16)
N1	0.050 (2)	0.0351 (18)	0.041 (2)	0.0025 (17)	0.0151 (16)	−0.0019 (17)
C9	0.074 (4)	0.043 (3)	0.059 (3)	−0.003 (2)	0.025 (2)	0.006 (2)
C2	0.045 (2)	0.042 (3)	0.037 (2)	0.006 (2)	0.0100 (17)	−0.0013 (19)
C4	0.055 (3)	0.045 (3)	0.036 (2)	−0.001 (2)	0.0162 (19)	−0.0062 (19)
C7	0.068 (3)	0.041 (3)	0.042 (2)	0.004 (2)	0.014 (2)	−0.008 (2)
C3	0.056 (3)	0.040 (2)	0.045 (2)	−0.003 (2)	0.014 (2)	−0.0038 (19)
N2	0.063 (3)	0.048 (2)	0.047 (2)	−0.0019 (19)	0.0190 (17)	0.0003 (18)
C6	0.065 (3)	0.038 (2)	0.045 (3)	0.001 (2)	0.013 (2)	−0.006 (2)
C1	0.059 (3)	0.039 (3)	0.042 (2)	0.006 (2)	0.010 (2)	0.003 (2)
C5	0.042 (2)	0.040 (2)	0.038 (2)	0.0084 (18)	0.0089 (18)	0.0003 (19)
C8	0.059 (3)	0.041 (2)	0.042 (3)	0.002 (2)	0.015 (2)	−0.0038 (18)
C10	0.072 (3)	0.036 (2)	0.064 (3)	0.000 (2)	0.030 (3)	−0.003 (2)

O1—C1	1.321 (6)	C4—C3	1.385 (5)
O1—H1	0.8200	C4—C5	1.384 (5)
O2—C1	1.207 (5)	C4—H4	0.9300
N1—C8	1.350 (5)	C7—C6	1.382 (6)
N1—C10	1.378 (5)	C7—H7	0.9300
N1—C5	1.423 (5)	C3—H3	0.9300
C9—C10	1.345 (6)	N2—C8	1.313 (5)
C9—N2	1.368 (6)	C6—C5	1.385 (5)
C9—H9	0.9300	C6—H6	0.9300
C2—C7	1.388 (6)	C8—H8	0.9300
C2—C3	1.388 (6)	C10—H10	0.9300
C2—C1	1.483 (6)
C1—O1—H1	109.5	C2—C3—H3	119.6
C8—N1—C10	105.5 (4)	C8—N2—C9	105.1 (4)
C8—N1—C5	126.9 (3)	C7—C6—C5	119.5 (4)
C10—N1—C5	127.7 (3)	C7—C6—H6	120.3
C10—C9—N2	110.1 (4)	C5—C6—H6	120.3
C10—C9—H9	124.9	O2—C1—O1	123.1 (4)
N2—C9—H9	124.9	O2—C1—C2	122.8 (4)
C7—C2—C3	118.4 (4)	O1—C1—C2	114.1 (4)
C7—C2—C1	119.3 (4)	C4—C5—C6	120.0 (4)
C3—C2—C1	122.3 (4)	C4—C5—N1	119.5 (4)
C3—C4—C5	120.0 (4)	C6—C5—N1	120.5 (4)
C3—C4—H4	120.0	N2—C8—N1	112.5 (4)
C5—C4—H4	120.0	N2—C8—H8	123.7
C6—C7—C2	121.3 (4)	N1—C8—H8	123.7
C6—C7—H7	119.3	C9—C10—N1	106.8 (4)
C2—C7—H7	119.3	C9—C10—H10	126.6
C4—C3—C2	120.8 (4)	N1—C10—H10	126.6
C4—C3—H3	119.6
C3—C2—C7—C6	−2.3 (7)	C7—C6—C5—C4	−0.1 (6)
C1—C2—C7—C6	178.7 (4)	C7—C6—C5—N1	−178.8 (4)
C5—C4—C3—C2	0.7 (6)	C8—N1—C5—C4	−14.9 (6)
C7—C2—C3—C4	1.0 (7)	C10—N1—C5—C4	167.0 (4)
C1—C2—C3—C4	179.9 (4)	C8—N1—C5—C6	163.9 (4)
C10—C9—N2—C8	0.1 (5)	C10—N1—C5—C6	−14.3 (7)
C2—C7—C6—C5	1.9 (7)	C9—N2—C8—N1	0.1 (5)
C7—C2—C1—O2	0.5 (7)	C10—N1—C8—N2	−0.3 (5)
C3—C2—C1—O2	−178.4 (5)	C5—N1—C8—N2	−178.7 (4)
C7—C2—C1—O1	−178.1 (5)	N2—C9—C10—N1	−0.3 (6)
C3—C2—C1—O1	3.0 (6)	C8—N1—C10—C9	0.4 (5)
C3—C4—C5—C6	−1.2 (6)	C5—N1—C10—C9	178.8 (4)
C3—C4—C5—N1	177.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2i	0.82	1.83	2.645 (5)	178
C9—H9···O2ii	0.93	2.42	3.332 (6)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2i	0.82	1.83	2.645 (5)	178
C9—H9⋯O2ii	0.93	2.42	3.332 (6)	168

Symmetry codes: (i) ; (ii) .