2-[3-(1H-Benzimidazol-2-yl)prop­yl]-1-decyl-1H-benzimidazole

Hamid Ennajih; Rachid Bouhfid; El Mokhtar Essassi; Seik Weng Ng

doi:10.1107/S160053681103501X

. 2011 Aug 31;67(Pt 9):o2544. doi: 10.1107/S160053681103501X

2-[3-(1H-Benzimidazol-2-yl)propyl]-1-decyl-1H-benzimidazole

Hamid Ennajih ^a, Rachid Bouhfid ^a, El Mokhtar Essassi ^b, Seik Weng Ng ^c,^d,^*

PMCID: PMC3200644 PMID: 22064906

Abstract

The asymmetric unit of the title compound, C₂₇H₃₆N₄, contains two independent molecules. Except for the atoms of the decyl chain, the non-H atoms of each molecule are approximately coplanar (r.m.s. deviations = 0.075 and 0.164 Å) and the –CH₂CH₂CH₂– link connecting the two benzimidazolyl fused-ring systems is slightly opened up at the middle C atom. The decyl substituent adopts an extended zigzag conformation in both molecules. In the crystal, adjacent molecules interact by N—H⋯N hydrogen bonds, generating a chain parallel to the c axis.

Related literature

For 2,2′-(propane-1,3-diyl)bis(benzimidazolium) dichloride and hydrogen perchlorate, see: Hu et al. (2006 ▶); Sun et al. (2004 ▶).

Experimental

Crystal data

C₂₇H₃₆N₄
M _r = 416.60
Monoclinic,
a = 38.5580 (6) Å
b = 13.2052 (2) Å
c = 9.9623 (2) Å
β = 95.339 (1)°
V = 5050.46 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker APEXII diffractometer
38663 measured reflections
9083 independent reflections
5547 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.165
S = 1.02
9083 reflections
567 parameters
36 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103501X/xu5311sup1.cif

e-67-o2544-sup1.cif^{(36.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103501X/xu5311Isup2.hkl

e-67-o2544-Isup2.hkl^{(444.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681103501X/xu5311Isup3.cml

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
N1—H1⋯N2ⁱ	0.88 (1)	1.96 (1)	2.813 (2)	162 (2)
N5—H5⋯N6ⁱⁱ	0.88 (1)	2.01 (1)	2.860 (2)	162 (2)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

We thank MAScIR, Université Mohammed V-Agdal and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Bis(2-benzimidazolyl)alkanes exhibit anti-viral activity; they are also N-heterocyclic compounds that form complexes with a range of metal salts. The crystal structure of the n-propane derivative is known as its chloride and hydrogen perchlorate salts (Hu et al., 2006; Sun et al., 2004). The nitrogen-bound hydrogen can be removed and the resulting anion used as a nucleophile in reacting with haloalkanes. In this study, the alkane is a ten-carbon chain; however, only one of the two H atoms can be removed. Except for the atoms of the decyl chain, the non-hydrogen atoms of the molecule of C₂₇H₂₆N₄ (Scheme I) lie on an approximate plane and the –CH₂CH₂CH₂– link connecting the two benzimidazolyl fused-ring systems is slightly opened up at the middle carbon (Fig. 1). The decyl substitutent adopts an extended zigzag conformation. Adjacent molecules interact by N–H···N hydrogen bonds to generate a chain parallel to the c-axis of the monoclinic unit cell (Table 1).

Experimental

To 1,3-bis(1H-benzmidazol-2-yl)propane (0.50 g, 1.8 mmol), potassium carbonate (0.82 g, 6 mmol), and tetra-n-butylammonium bromide (0.01 g, 0.03 mmol) in DMF (30 ml) was added 1-bromodecane (0.75 ml, 3.6 mmol). The mixturewas stirred for 48 h. After the completion of the reaction (as monitored byTLC), the inorganic salts were filtered and the solvent was removed under reduced pressure. The residue was purified by crystallization from ethanol. Colorless crystals were isolated.