1,3,5-Tris(N-phenyl­benzimidazol-2-yl)benzene methanol solvate

Song, W.-F.; Wu, Y.; Fan, Y.; Wang, Y.; Liu, Y.

doi:10.1107/S1600536809036046

Volume 65
Part 10
Page o2461
October 2009

Received 9 July 2009
Accepted 7 September 2009
Online 12 September 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.051
wR = 0.142
Data-to-parameter ratio = 17.3
Details

1,3,5-Tris(N-phenylbenzimidazol-2-yl)benzene methanol solvate

Wei-Feng Song,^a Ying Wu,^a Yan Fan,^a Yue Wang ^a and Yu Liu ^a ^*

^aState Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, People's Republic of China
Correspondence e-mail: yuliu@jlu.edu.cn

The main molecule of the title compound, C₄₅H₃₀N₆·CH₃OH, has a non-planar core: the dihedral angles between the benzimidazole rings and the central benzene ring are 20.19 (10), 34.57 (8), and 44.59 (8)°, while the dihedral angles between the peripheral phenyl rings and the attached benzimidazole rings are 84.57 (7), 62.71 (6) and 51.73 (6)°. The tri-substituted benzene molecule is connected to the methanol solvent molecule through an O-HN hydrogen bond, forming a 1:1 solvate. In the crystal structure, no significant [pi] - [pi] interactions are present, and the molecules are associated through weak C-HN and C-HO(methanol) contacts.

Related literature

For OLEDs (organic light emitting diodes), see: Adachi et al. (2001); Gao et al. (1999); Shi et al. (1997); Lo et al. (2002). For the structure of a related solvate, see: Totsatitpaisan et al. (2008).

Experimental

Crystal data

C₄₅H₃₀N₆·CH₄O
M_r = 686.79
Monoclinic, P 2₁ /c
a = 11.253 (2) Å
b = 18.692 (4) Å
c = 17.763 (4) Å
= 101.58 (3)°
V = 3660.1 (13) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.26 × 0.20 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.981, T_max = 0.986
35250 measured reflections
8285 independent reflections
4831 reflections with I > 2(I)
R_int = 0.058

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.142
S = 1.01
8285 reflections
480 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O-H0N1ⁱ	0.82	2.12	2.936 (2)	170
C25-H25N5ⁱⁱ	0.93	2.69	3.603 (3)	169
C37-H37N4ⁱⁱⁱ	0.93	2.43	3.338 (3)	164
C32-H32O^iv	0.93	2.71	3.605 (3)	161
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y+1, -z+1; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2239 ).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 50733002) and the Jilin Provincial Science and Technology Bureau (grant No. 20070107).

References

Adachi, C., Baldo, M. A., Forrest, S. R., Lamansky, S., Thompson, M. E. & Kwong, R. C. (2001). Appl. Phys. Lett. 78, 1622-1624.
Gao, Z., Lee, C. S., Bello, I., Lee, S. T., Chen, R.-M., Luh, T.-Y., Shi, J. & Tang, C. W. (1999). Appl. Phys. Lett. 74, 865-867.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Lo, S.-C., Male, N. A. H., Markham, J. P. J., Magennis, S. W., Burn, P. L., Salata, O. V. & Samuel, I. D. W. (2002). Adv. Mater. 14, 975-979.
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shi, J., Tang, C. W. & Chen, C. H. (1997). US Patent 5645948.
Totsatitpaisan, P., Tashiro, K. & Chirachanchai, S. (2008). J. Phys. Chem. A, 112, 10348-10358.

organic compounds