1-Carb­oxy­methyl-3-octylimidazolium bromide

Nassir N Al-Mohammed; Yatimah Alias; Zanariah Abdullah; Hamid Khaledi

doi:10.1107/S1600536811022094

. 2011 Jun 18;67(Pt 7):o1701. doi: 10.1107/S1600536811022094

1-Carboxymethyl-3-octylimidazolium bromide

Nassir N Al-Mohammed ^a, Yatimah Alias ^a, Zanariah Abdullah ^a, Hamid Khaledi ^a,^*

PMCID: PMC3152140 PMID: 21837097

Abstract

In the title compound, C₁₃H₂₃N₂O₂ ⁺·Br⁻, the octyl chain has an all-trans conformation. In the crystal, the cations are linked by C—H⋯O bonds into a zigzag chain along the b axis. The bromide anions further link the chains via C—H⋯Br interactions into a two-dimensional array parallel to the ab plane. An O—H⋯Br interaction is also observed.

Related literature

For related structures, see: Wei et al. (2009 ▶); Chen et al. (2009 ▶).

Experimental

Crystal data

C₁₃H₂₃N₂O²⁺·Br⁻
M _r = 319.24
Monoclinic,
a = 7.6745 (2) Å
b = 4.6176 (1) Å
c = 41.8663 (9) Å
β = 92.167 (1)°
V = 1482.59 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.77 mm⁻¹
T = 100 K
0.21 × 0.19 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.594, T _max = 0.851
10905 measured reflections
2761 independent reflections
2678 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.095
S = 1.43
2761 reflections
167 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.25 e Å⁻³
Δρ_min = −2.19 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536811022094/is2721sup1.cif

e-67-o1701-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022094/is2721Isup2.hkl

e-67-o1701-Isup2.hkl^{(135.6KB, 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
C6—H6B⋯Br1ⁱ	0.99	2.89	3.772 (4)	148
C5—H5⋯Br1ⁱⁱ	0.95	2.91	3.681 (4)	139
C4—H4⋯O2ⁱⁱⁱ	0.95	2.25	3.151 (5)	158
C3—H3⋯Br1ⁱ	0.95	2.82	3.593 (4)	139
C2—H2B⋯Br1^iv	0.99	2.90	3.676 (4)	136
C2—H2A⋯O2^v	0.99	2.44	3.328 (5)	150
O1—H1⋯Br1	0.84 (2)	2.33 (2)	3.153 (3)	168 (4)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

The authors thank the University of Malaya for funding this study (FRGS grant No. FP001/2010 A).

supplementary crystallographic information

Comment

The imidazolium ring is N-bound to a long alkyl chain, namely an octyl chain, and a carboxymethyl group. The alkyl chain adopts an all-trans conformation, as observed in similar structures (Wei et al., 2009; Chen et al., 2009). The carboxy group and the imidazolium ring subtend an N1—C2—C1 angle of 110.7 (3)°. In the crystal, the cationic moieties are bonded via C—H···O interactions (Table 1) into infinite chains along the b axis. The bromide anions link the cationic chains through C—H···Br interactions into layers parallel to the ab plane (Fig. 2).

Experimental

A solution of bromoacetic acid (1 g, 7.2 mmol) and octylimidazole (1.29 g, 7.2 mmol) in dry 1,4-dioxane (10 ml) was stirred under nitrogen atmosphere at 70 °C for 7 hr. The solution was then poured into dichloromethane (25 ml) and extracted with distilled water (50 ml). The aqueous solution was evaporated under vacuum to give a viscous oil which crystallized from THF to yield the colorless crystals of the title compound.