2-[1-(3-Oxo-1,3-dihydro-2-benzofuran-1-yl)-1H-benzimidazol-2-yl]benzoic acid methanol solvate

Shi, G.; Ma, L.; Deng, H.

doi:10.1107/S1600536810026851

Volume 66
Part 8
Page o2034
August 2010

Received 20 June 2010
Accepted 7 July 2010
Online 17 July 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.058
wR = 0.179
Data-to-parameter ratio = 13.3
Details

2-[1-(3-Oxo-1,3-dihydro-2-benzofuran-1-yl)-1H-benzimidazol-2-yl]benzoic acid methanol solvate

Guang Shi,^a Li Ma ^a and Hong Deng ^a ^*

^aSchool of Chemistry and Environment, South China Nomal University, Guangzhou 510006, People's Republic of China
Correspondence e-mail: dh@scnu.edu.cn

The condensation of 2-carboxybenzaldehyde with 1,2-phenylenediamine unexpectedly yielded the title compound, C₂₂H₁₄N₂O₄·CH₄O. The benzimidazole ring system is almost perpendicular to the phthalazine ring system, making a dihedral angle of 88.4 (5)°. Intermolecular O-HN and O-HO hydrogen-bonding interactions stabilize the crystal structure.

Related literature

For hydrogen bonding, see: Scheiner (1997). For the role of hydrogen bonding between solvent molecules and heterocyclic compounds in the formation of supramolecules, see: Amaya & Rebek (2004); Roesky & Andruh (2003). Nelson et al. (1982) have reported that reaction of 2,6-diacetylpyridine and 1,2-phenylenediamine can form benzimidazole groups via oxidative dehydrogenation and Li et al. (2002) have isolated a benzimidazole derivate by the reaction of 5-bromo-2-hydroxybenzaldehyde and 1,2-phenylenediamine in the presence of anhydrous ethanol solution. For a related structure, see: Zhang et al. (2009).

Experimental

Crystal data

C₂₂H₁₄N₂O₄·CH₄O
M_r = 402.39
Monoclinic, P 2₁ /c
a = 13.7946 (8) Å
b = 9.7815 (7) Å
c = 15.3083 (9) Å
= 103.985 (4)°
V = 2004.4 (2) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.972, T_max = 0.981
16115 measured reflections
3618 independent reflections
2220 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.179
S = 1.07
3618 reflections
273 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O5	0.82	1.83	2.632 (4)	167
O5-H5AN1ⁱ	0.82	1.92	2.733 (3)	173
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2172 ).

Acknowledgements

The authors acknowledge South China Normal University for supporting this work.

References

Amaya, T. & Rebek, J. (2004). J. Am. Chem. Soc. 126, 14149-14156.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Li, J., Zhang, F. X. & Shi, Q. Z. (2002). Chin. J. Inorg. Chem. 6, 643-645.
Nelson, S. M., Esho, F. S. & Drew, M. G. B. (1982). J. Chem. Soc. Dalton Trans. pp. 407-415.
Roesky, H. W. & Andruh, M. (2003). Coord. Chem. Rev. 236, 91-119.
Scheiner (1997). Please give full reference.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhang, Y.-L., Wu, Y.-J., Peng, G. & Deng, H. (2009). Acta Cryst. E65, o974.

organic compounds

2-[1-(3-Oxo-1,3-dihydro-2-benzofuran-1-yl)-1H-benzimidazol-2-yl]benzoic acid methanol solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References