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4-(Imidazol-1-yl)benzoic acid

aDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, and Key Laboratory of Functional Inorganic Materials Chemistry, Hefei 230039, People's Republic of China
*Correspondence e-mail: zhpzhp@263.net

(Received 30 December 2010; accepted 25 January 2011; online 29 January 2011)

In the title mol­ecule, C10H8N2O2, the imidazole and benzene rings form a dihedral angle of 14.5 (1)°. In the crystal, inter­molecular O—H⋯N hydrogen bonds link the mol­ecules into chains extending in [[\overline{1}]01], which are further linked into sheets parallel to (102) through weak C—H⋯O inter­actions.

Related literature

The crystal structures of the Cd and Co complexes with the title mol­ecule were described by Gao et al. (2009[Gao, J., Wei, K. J., Ni, J. & Zhang, J. Z. (2009). J. Coord. Chem. 62, 257-265.]) and Zhang et al. (2007[Zhang, J. Z., Cao, W. R., Pan, J. X. & Chen, Q. W. (2007). Inorg. Chem. Commun. 10, 1360-1364.]), respectively.

[Scheme 1]

Experimental

Crystal data
  • C10H8N2O2

  • Mr = 188.18

  • Monoclinic, P c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.969, Tmax = 0.979

  • 2483 measured reflections

  • 782 independent reflections

  • 626 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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) [x-1, -y, z+{\script{1\over 2}}]; (ii) [x+1, -y+1, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The molecules of the title compound, (I), are often used as coordinating ligands in the metal complexes (Gao et al., 2009; Zhang et al., 2007). Herewith we presenet the crystal structure of (I).

In (I) (Fig.1), the imidazole ring is twisted out of the plane of benzene ring at 14.5 (1)°. In the crystal structure, intermolecular O—H···N hydrogen bonds (Table 1) link the molecules into chains extended in direction [-101]. These chains are further linked into sheets parallel to the plane (102) through the weak C—H···O interactions (Table 1).

Related literature top

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 top

A 150 ml round-bottom flask was charged with a magnetic stirrer and a reflux condenser, iminazole (44 mmol), K2CO3 (6.00 g, 43 mmol), 30 ml DMSO and a little Aliquat 336 were added. 4-fluorobenzaldehyde (4.5 ml, 42 mmol) was added dropwise to the mixture at 363 K and stirred for 15 min. Then the reaction mixture was refluxed for 24 h at 353 K, cooled to room temperature, poured into 150 ml ice-water and filtered. The primrose yellow crude product was obtained, washed with distilled water, and dried in vacuo at room temperature, then purified by recrystallization with ethyl acetate to give the desired analytical pure intermediate products. Intermediate product (12.5 mmol) and 15 ml 20% (wt) NaOH (aq) were added to a round-bottom flask equipped with a magnetic stirrer and a reflux condenser at 333 K for 30 min. Then AgNO3 (4.00 g, 24 mmol) was added to the mixture group by group. The reaction mixture was refluxed for 24 h at 333 K, cooled to room temperature and filtered. Excessive HCl (1 M) was added to the filtrate and adjust pH to 2, a great deal of sediments were obtained and then filtered. The crude product was recrystallized with ethanol. 4-imidazolylbenzoic acid: Yellow crystals. Weight: 1.44 g, Yield: 64%.

Refinement top

All hydrogen atoms were placed in geometrically idealized positions (O—H = 0.82 Å, C—H = 0.93 Å) and constrained to ride on their parent atoms, with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(O). Due to the absence of any significant anomalous scatterers in the molecule, the 408 Friedel pairs were merged before the final refinement.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids.
4-(Imidazol-1-yl)benzoic acid top
Crystal data top
C10H8N2O2F(000) = 196
Mr = 188.18Dx = 1.470 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
a = 4.1443 (11) ÅCell parameters from 553 reflections
b = 6.6561 (19) Åθ = 2.6–21.0°
c = 15.706 (4) ŵ = 0.11 mm1
β = 101.023 (7)°T = 296 K
V = 425.3 (2) Å3Prism, yellow
Z = 20.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART CCD
diffractometer
782 independent reflections
Radiation source: fine-focus sealed tube626 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ϕ and ω scansθmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 34
Tmin = 0.969, Tmax = 0.979k = 78
2483 measured reflectionsl = 1819
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-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 parametersΔρmax = 0.14 e Å3
2 restraintsΔρmin = 0.17 e Å3
Crystal data top
C10H8N2O2V = 425.3 (2) Å3
Mr = 188.18Z = 2
Monoclinic, PcMo Kα radiation
a = 4.1443 (11) ŵ = 0.11 mm1
b = 6.6561 (19) ÅT = 296 K
c = 15.706 (4) Å0.30 × 0.20 × 0.20 mm
β = 101.023 (7)°
Data collection top
Bruker SMART CCD
diffractometer
782 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
626 reflections with I > 2σ(I)
Tmin = 0.969, Tmax = 0.979Rint = 0.032
2483 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0402 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 0.71Δρmax = 0.14 e Å3
782 reflectionsΔρmin = 0.17 e Å3
128 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
xyzUiso*/Ueq
O10.4877 (9)0.2462 (5)0.4370 (2)0.0588 (9)
H10.42730.29690.47890.088*
O20.5637 (9)0.0207 (5)0.52362 (19)0.0599 (10)
N11.0752 (8)0.3543 (5)0.1902 (2)0.0415 (9)
C91.2725 (12)0.5824 (7)0.1140 (3)0.0569 (13)
H91.34080.70490.09520.068*
C20.7016 (11)0.0470 (6)0.3847 (3)0.0413 (10)
C40.8260 (11)0.0591 (6)0.2410 (3)0.0444 (11)
H40.82670.00250.18780.053*
C70.8116 (11)0.2437 (7)0.3973 (3)0.0499 (11)
H70.80120.30790.44930.060*
C30.7080 (10)0.0435 (7)0.3054 (3)0.0462 (11)
H30.63220.17450.29540.055*
N21.2859 (9)0.4028 (6)0.0725 (2)0.0518 (10)
C60.9360 (11)0.3462 (7)0.3342 (3)0.0491 (12)
H61.01470.47660.34430.059*
C10.5766 (11)0.0580 (6)0.4551 (3)0.0465 (11)
C50.9428 (9)0.2532 (6)0.2556 (3)0.0399 (10)
C81.1662 (11)0.2706 (7)0.1202 (2)0.0466 (11)
H81.14630.13430.10710.056*
C101.1460 (13)0.5559 (7)0.1859 (3)0.0548 (12)
H101.11280.65470.22520.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.088 (3)0.047 (2)0.0476 (17)0.0050 (18)0.0288 (17)0.0015 (14)
O20.094 (3)0.049 (2)0.0417 (17)0.0028 (19)0.0252 (18)0.0047 (16)
N10.050 (2)0.0351 (18)0.041 (2)0.0025 (17)0.0151 (16)0.0019 (17)
C90.074 (4)0.043 (3)0.059 (3)0.003 (2)0.025 (2)0.006 (2)
C20.045 (2)0.042 (3)0.037 (2)0.006 (2)0.0100 (17)0.0013 (19)
C40.055 (3)0.045 (3)0.036 (2)0.001 (2)0.0162 (19)0.0062 (19)
C70.068 (3)0.041 (3)0.042 (2)0.004 (2)0.014 (2)0.008 (2)
C30.056 (3)0.040 (2)0.045 (2)0.003 (2)0.014 (2)0.0038 (19)
N20.063 (3)0.048 (2)0.047 (2)0.0019 (19)0.0190 (17)0.0003 (18)
C60.065 (3)0.038 (2)0.045 (3)0.001 (2)0.013 (2)0.006 (2)
C10.059 (3)0.039 (3)0.042 (2)0.006 (2)0.010 (2)0.003 (2)
C50.042 (2)0.040 (2)0.038 (2)0.0084 (18)0.0089 (18)0.0003 (19)
C80.059 (3)0.041 (2)0.042 (3)0.002 (2)0.015 (2)0.0038 (18)
C100.072 (3)0.036 (2)0.064 (3)0.000 (2)0.030 (3)0.003 (2)
Geometric parameters (Å, º) top
O1—C11.321 (6)C4—C31.385 (5)
O1—H10.8200C4—C51.384 (5)
O2—C11.207 (5)C4—H40.9300
N1—C81.350 (5)C7—C61.382 (6)
N1—C101.378 (5)C7—H70.9300
N1—C51.423 (5)C3—H30.9300
C9—C101.345 (6)N2—C81.313 (5)
C9—N21.368 (6)C6—C51.385 (5)
C9—H90.9300C6—H60.9300
C2—C71.388 (6)C8—H80.9300
C2—C31.388 (6)C10—H100.9300
C2—C11.483 (6)
C1—O1—H1109.5C2—C3—H3119.6
C8—N1—C10105.5 (4)C8—N2—C9105.1 (4)
C8—N1—C5126.9 (3)C7—C6—C5119.5 (4)
C10—N1—C5127.7 (3)C7—C6—H6120.3
C10—C9—N2110.1 (4)C5—C6—H6120.3
C10—C9—H9124.9O2—C1—O1123.1 (4)
N2—C9—H9124.9O2—C1—C2122.8 (4)
C7—C2—C3118.4 (4)O1—C1—C2114.1 (4)
C7—C2—C1119.3 (4)C4—C5—C6120.0 (4)
C3—C2—C1122.3 (4)C4—C5—N1119.5 (4)
C3—C4—C5120.0 (4)C6—C5—N1120.5 (4)
C3—C4—H4120.0N2—C8—N1112.5 (4)
C5—C4—H4120.0N2—C8—H8123.7
C6—C7—C2121.3 (4)N1—C8—H8123.7
C6—C7—H7119.3C9—C10—N1106.8 (4)
C2—C7—H7119.3C9—C10—H10126.6
C4—C3—C2120.8 (4)N1—C10—H10126.6
C4—C3—H3119.6
C3—C2—C7—C62.3 (7)C7—C6—C5—C40.1 (6)
C1—C2—C7—C6178.7 (4)C7—C6—C5—N1178.8 (4)
C5—C4—C3—C20.7 (6)C8—N1—C5—C414.9 (6)
C7—C2—C3—C41.0 (7)C10—N1—C5—C4167.0 (4)
C1—C2—C3—C4179.9 (4)C8—N1—C5—C6163.9 (4)
C10—C9—N2—C80.1 (5)C10—N1—C5—C614.3 (7)
C2—C7—C6—C51.9 (7)C9—N2—C8—N10.1 (5)
C7—C2—C1—O20.5 (7)C10—N1—C8—N20.3 (5)
C3—C2—C1—O2178.4 (5)C5—N1—C8—N2178.7 (4)
C7—C2—C1—O1178.1 (5)N2—C9—C10—N10.3 (6)
C3—C2—C1—O13.0 (6)C8—N1—C10—C90.4 (5)
C3—C4—C5—C61.2 (6)C5—N1—C10—C9178.8 (4)
C3—C4—C5—N1177.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N2i0.821.832.645 (5)178
C9—H9···O2ii0.932.423.332 (6)168
Symmetry codes: (i) x1, y, z+1/2; (ii) x+1, y+1, z1/2.

Experimental details

Crystal data
Chemical formulaC10H8N2O2
Mr188.18
Crystal system, space groupMonoclinic, Pc
Temperature (K)296
a, b, c (Å)4.1443 (11), 6.6561 (19), 15.706 (4)
β (°) 101.023 (7)
V3)425.3 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.969, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
2483, 782, 626
Rint0.032
(sin θ/λ)max1)0.605
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.104, 0.71
No. of reflections782
No. of parameters128
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.17

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N2i0.821.832.645 (5)178
C9—H9···O2ii0.932.423.332 (6)168
Symmetry codes: (i) x1, y, z+1/2; (ii) x+1, y+1, z1/2.
 

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 21071001), the Education Committee of Anhui Province (KJ2009A52, KJ2010A30), the Team for Scientific Innovation Foundation of Anhui Province (2006 K J007TD), the Ministry of Education and Person with Ability Foundation of Anhui University, the Science and Technological Fund of Anhui Province for Outstanding Youth (10040606Y22) and the 211 Project of Anhui University.

References

First citationBruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGao, J., Wei, K. J., Ni, J. & Zhang, J. Z. (2009). J. Coord. Chem. 62, 257–265.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhang, J. Z., Cao, W. R., Pan, J. X. & Chen, Q. W. (2007). Inorg. Chem. Commun. 10, 1360–1364.  Web of Science CSD CrossRef CAS Google Scholar

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