1,3-Bis(3-phenyl­prop­yl)-1H-1,3-benzimidazole-2(3H)-selone

Mehmet Akkurt; Ülkü Yılmaz; Hasan Küçükbay; Orhan Büyükgüngör

doi:10.1107/S1600536811013985

. 2011 Apr 22;67(Pt 5):o1179. doi: 10.1107/S1600536811013985

1,3-Bis(3-phenylpropyl)-1H-1,3-benzimidazole-2(3H)-selone

Mehmet Akkurt ^a,^*, Ülkü Yılmaz ^b, Hasan Küçükbay ^b, Orhan Büyükgüngör ^c

PMCID: PMC3089112 PMID: 21754482

Abstract

The title molecule, C₂₅H₂₆N₂Se, has mirror symmetry, with the mirror plane passing through the atoms of the C=Se bond and the mid-points of the two C—C bonds of the benzene ring of the benzimidazole group. The dihedral angle between the benzimidazole ring system and the phenyl ring is 71.62 (14)°.

Related literature

For general background to benzimidazole derivatives, see: Aydın et al. (1998 ▶); Böhm & Herrmann (2000 ▶); Küçükbay et al. (1996 ▶, 1997 ▶); Lappert et al. (2009 ▶); Wanzlick & Schikora (1960 ▶); Yıldırım et al. (2006 ▶); Yılmaz & Küçükbay (2009 ▶); Çetinkaya et al. (1994 ▶, 1998 ▶). For related structures, see: Akkurt et al. (2004 ▶); Aydın et al. (1999 ▶); Yalçın et al. (2008 ▶).

Experimental

Crystal data

C₂₅H₂₆N₂Se
M _r = 433.44
Tetragonal,
a = 10.5150 (3) Å
c = 19.8142 (8) Å
V = 2190.76 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.73 mm⁻¹
T = 296 K
0.68 × 0.58 × 0.52 mm

Data collection

Stowe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.322, T _max = 0.408
16780 measured reflections
2531 independent reflections
2225 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.066
S = 1.07
2531 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ▶), 1003 Freidel pairs
Flack parameter: 0.004 (12)

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013985/qm2004sup1.cif

e-67-o1179-sup1.cif^{(23.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013985/qm2004Isup2.hkl

e-67-o1179-Isup2.hkl^{(124.4KB, hkl)}

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

supplementary crystallographic information

Comment

Electron-rich olefins (EROs) have been attracted considerable attention in both organic and inorganic preparative literature due to their unique properties as reagent and reaction intermediates since their first report by Wanzlick in 1960 (Wanzlick & Schikora, 1960; Böhm & Herrmann, 2000).

Benzimidazolium salts are convenient precursors for EROs through reacting with a strong base such as NaH comparing with other methods such as reacting a secondary amine (N,N'-disubstituted-1,2-diaminobenzene) with an acetal, chloral or triethyl orthoformate. We have synthesized and isolated first time the ERO, bis(1,3-dimethybenzimidazolidine-2-ylidene) (Çetinkaya et al., 1994). We have also synthesized a number of EROs using different synthesis methods and used them to synthesize many organic or organometallic compounds (Küçükbay et al., 1996, Küçükbay et al., 1997, Çetinkaya et al., 1998; Aydın et al., 1998 Yıldırım et al., 2006; Yılmaz & Küçükbay, 2009). Their electron-richness confers on them a very high reactivity as strong nucleophiles, which assist in the preparation of numerous products by reaction, amongst others, with group 16 elements, transition metals, and many protic compounds (Lappert et al., 2009). It is known that the ultimate oxidation product of EROs with air is urea; sulfur, selenium and tellurium react similarly to give the corresponding analogues. The objective of the present study was to elucidate the crystal structure of the title compound which is new ERO derivative.

In the title molecule (I), Fig. 1, the Se═C bond length is 1.828 (2) Å, and this value is similar to those [1.829 (3) Å] found in 1-ethyl-3-(2-phenylethyl)benzimidazole-2-selone (Akkurt et al., 2004) and [1.825 (7) Å] found in 1,3-dimethylbenzimidazole-2-selone (Aydın et al., 1999), and is shorter than that [2.058 (4) Å] found for the Te═ C bond length in 1,3-bis(3-phenylpropyl)1H-benzimidazole- 2(3H)-tellurone (Yalçın et al., 2008).

The molecular structure is stabilized by a weak C—H···Se interaction (Table 1). The benzimidazole ring system (N1/C10/C11/C12/C13/N1a/C11a/C12a/C13a) of (I) is planar (r.m.s deviation of fitted atoms is 0.09 (3) Å). The dihedral angle between the phenyl ring (C1–C6) and the benzimidazole ring is 71.62 (14)°. The molecular packing in (I) is shown in Fig. 2.

Experimental

A mixture of bis(1,3-di(3-phenylpropyl)benzimidazolidine-2-ylidene) (0.68 g, 0.96 mmol) and selenium (0.15 g, 1.90 mmol) in dry toluene (10 ml) was heated under reflux for 2 h. Then the mixture was filtered to remove unreacted selenium and all volatiles were removed in vacuo (0.02 m mH g). The crude product was crystallized from alcohol upon cooling to 243 K. Yield: 0.63 g, 76%; m.p.: 439–441 K; v_(CSe)= 1480 cm^-1. Anal. found: C 69.58, H 5.98, N 6.38%. Calculated for C₂₅H₂₆N₂Se: C 69.27, H 6.05, N 6.46%. ¹H-NMR (δ, CDCl₃): 7.26–7.06 (m, 14H, Ar—H), 4.47 (t, 4H, NCH₂CH₂CH₂C₆H₅, J = 7.8 Hz), 2.81 (t, 4H, NCH₂CH₂CH₂C₆H₅, J = 7.8 Hz), 2.23 (quint, 4H, NCH₂CH₂CH₂C₆H₅, J = 7.8 Hz). ¹³C-NMR (δ, CDCl₃): 165.7 (C=Se), 140.8, 132.9, 128.5, 128.4, 126.2, 123.2 and 109.5 (Ar-C), 46.1 (NCH₂CH₂CH₂C₆H₅), 33.0 (NCH₂CH₂CH₂C₆H₅), 29.3 (NCH₂CH₂CH₂C₆H₅).