4-(1-Ethyl-1H-1,3-benzimidazol-2-yl)-N,N-diphenyl­aniline monohydrate

Tao Wu; Kai Wang; Peng Jiang; Hong-Jun Zhu

doi:10.1107/S160053681100119X

. 2011 Jan 15;67(Pt 2):o417. doi: 10.1107/S160053681100119X

4-(1-Ethyl-1H-1,3-benzimidazol-2-yl)-N,N-diphenylaniline monohydrate

Tao Wu ^a, Kai Wang ^a, Peng Jiang ^a, Hong-Jun Zhu ^a,^*

PMCID: PMC3051646 PMID: 21523087

Abstract

In the title compound, C₂₇H₂₃N₃O·H₂O, the benzimidazole ring system has an r.m.s. deviation of 0.0071 Å and makes dihedral angles of 34.51 (2), 55.22 (3) and 41.05 (5)° with the central and N-bonded phenyl rings, respectively. In the crystal, the water molecular is connected to the organic molecule by intermolecular O—H⋯N hydrogen bonds. Weak intermolecular C—H⋯O hydrogen bonds also occur.

Related literature

For the synthetic procedure, see: Vinodkumar et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For background to the use of the title compound as an intermediate in the preparation of OLED materials, see: Kakimoto et al. (2008 ▶).

Experimental

Crystal data

C₂₇H₂₃N₃·H₂O
M _r = 407.50
Monoclinic,
a = 12.278 (3) Å
b = 9.2690 (19) Å
c = 19.468 (4) Å
β = 97.81 (3)°
V = 2195.0 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.978, T _max = 0.992
4223 measured reflections
4024 independent reflections
2487 reflections with I > 2σ(I)
R _int = 0.025
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.169
S = 1.01
4024 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100119X/bq2268sup1.cif

e-67-0o417-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100119X/bq2268Isup2.hkl

e-67-0o417-Isup2.hkl^{(197.2KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW—HWB⋯N2	0.85	2.50	2.903 (3)	110
OW—HWA⋯N2	0.85	2.49	2.903 (3)	111
C24—H24A⋯OWⁱ	0.93	2.43	3.352 (4)	173

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

The title compound, (I), is a kind of important organic intermediate which can be used for many fields such as OLED materials. (Kakimoto et al., 2008). We herein report its crystal structure.

In the molecule of (I), (Fig.1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The benzimidazole ring (A) is obviously almost coplanar with an r.m.s. deviation of 0.0071 °. The dihedral angles between A and the rest three phenyl rings B (C13-C18), C (C7-C12) and D (C1-C6) are 34.51 (2) ° 55.22 (3) ° and 41.05 (5) °, respectively. The H₂O molecule stems from the solvent ethanol, and the water molecular is connected with the target molecular by intermolecular C—H···O and O—H···N hydrogen bonds (Table 1), which seems to be very effective in the stabilization of the crystal structure.

Experimental

The title compound, (I) was synthesized according to the literature (Vinodkumar et al., 2008) The crystals were obtained by dissolving (I) (0.52 g, 1.28 mmol) in 25 ml ethanol and evaporating the solvent slowly at room temperature for about 7 d.