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organic compounds
1,3-Diallyl-2-methylbenzimidazolium bromide dihydrate
aInstitute of Nanomaterials and Nanotechnology, Avenue de l'Armée Royale, Madinat El Irfane, 10100 Rabat, Morocco, bCNRST Division of UATRS Angle Allal Fassi/FAR, BP 8027, Hay Riad, 10000 Rabat, Morocco, cLaboratoire de Chimie Organique Hétérocyclique, Pôle de compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
The bonds in the five-membered ring of the title hydrated salt, C14H17N2+·Br−·2H2O, are delocalized. The cation lies on a special position of m such that the mirror plane passes through the imidazolyl–methyl bond and is perpendicular to the plane of the cation. The anion lies on another special position of 2 The anion and uncoordinated water molecule are linked into a chain by O—H⋯O hydrogen bonds. One of the water O atoms is disordered over two sites of equal occupancy.
Related literature
For the et al. (2009). For those of the 1-allyl-3-(cyanobenzyl)benzimidazolium bromide and its hydrate, see: Xu et al. (2008
); Xu & Ye (2008
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2005); cell 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, 2009
).
Supporting information
10.1107/S1600536809034175/sj2636sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809034175/sj2636Isup2.hkl
2-Methylbenzimidazole (1 g, 7.5 mmol), potassium carbonate (1.55 g, 11.25 mmol) and tetra-n-butylammonium bromide (0.18 g, 0.75 mmol) were stirred in N,N-dimethylformamide (50 ml) for an hour. To this suspension was added ally bromide (1.96 ml, 22.5 mmol); the mixture was stirred for two days. The mixture was filtered and the solvent removed under vacuum. The residue was crystallized from ethanol to give yellow crystals in 60% yield; m.p. 516–518 K. The formulation was established by 1H– and 13C-NMR spectroscopic analysis.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.97 Å) and were included in the
in the riding model approximation, with U(H) set to 1.2U(C). The methyl H-atoms lie on general positions,and are disordered; their occupancies are all 0.5.The water H-atoms were located in a difference Fourier map and were refined with distance restraints (O–H 0.85±0.01 Å; H···H 1.39±0.01 Å). That hydrogen-bonded to Br1 is ordered whereas the other is disordered over two positions of 0.5 site occupancy. The isotropic temperature factors of the three H-atoms were refined.
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2009).C14H17N2+·Br−·2H2O | F(000) = 680 |
Mr = 329.24 | Dx = 1.402 Mg m−3 |
Monoclinic, C2/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2y | Cell parameters from 7035 reflections |
a = 13.2888 (2) Å | θ = 3.6–24.3° |
b = 16.8763 (2) Å | µ = 2.64 mm−1 |
c = 7.3897 (1) Å | T = 295 K |
β = 109.773 (1)° | Prism, yellow |
V = 1559.54 (4) Å3 | 0.4 × 0.3 × 0.2 mm |
Z = 4 |
Bruker APEXII diffractometer | 1851 independent reflections |
Radiation source: fine-focus sealed tube | 1497 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ϕ and ω scans | θmax = 27.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→17 |
Tmin = 0.403, Tmax = 0.590 | k = −21→19 |
11870 measured reflections | l = −8→9 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | w = 1/[σ2(Fo2) + (0.06P)2 + 0.349P] where P = (Fo2 + 2Fc2)/3 |
1851 reflections | (Δ/σ)max = 0.001 |
103 parameters | Δρmax = 0.31 e Å−3 |
6 restraints | Δρmin = −0.18 e Å−3 |
C14H17N2+·Br−·2H2O | V = 1559.54 (4) Å3 |
Mr = 329.24 | Z = 4 |
Monoclinic, C2/m | Mo Kα radiation |
a = 13.2888 (2) Å | µ = 2.64 mm−1 |
b = 16.8763 (2) Å | T = 295 K |
c = 7.3897 (1) Å | 0.4 × 0.3 × 0.2 mm |
β = 109.773 (1)° |
Bruker APEXII diffractometer | 1851 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1497 reflections with I > 2σ(I) |
Tmin = 0.403, Tmax = 0.590 | Rint = 0.024 |
11870 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 6 restraints |
wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Δρmax = 0.31 e Å−3 |
1851 reflections | Δρmin = −0.18 e Å−3 |
103 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br1 | 0.0000 | 0.691870 (15) | 0.5000 | 0.05502 (14) | |
O1 | 0.07379 (17) | 0.58143 (11) | 0.9005 (3) | 0.0787 (5) | |
H11 | 0.055 (2) | 0.6089 (13) | 0.796 (2) | 0.084 (9)* | |
H12 | 0.086 (3) | 0.5342 (9) | 0.874 (5) | 0.075 (18)* | 0.50 |
H13 | 0.021 (2) | 0.582 (2) | 0.942 (5) | 0.10 (2)* | 0.50 |
N1 | 0.34476 (11) | 0.56471 (8) | 0.6215 (2) | 0.0381 (3) | |
C1 | 0.1655 (2) | 0.5000 | 0.4821 (5) | 0.0557 (7) | |
H1A | 0.1386 | 0.4473 | 0.4841 | 0.083* | 0.50 |
H1B | 0.1472 | 0.5176 | 0.3514 | 0.083* | 0.50 |
H1C | 0.1343 | 0.5351 | 0.5507 | 0.083* | 0.50 |
C2 | 0.2831 (2) | 0.5000 | 0.5747 (4) | 0.0393 (5) | |
C3 | 0.45113 (13) | 0.54109 (10) | 0.7010 (2) | 0.0375 (4) | |
C4 | 0.54525 (15) | 0.58475 (12) | 0.7654 (3) | 0.0487 (5) | |
H4 | 0.5454 | 0.6399 | 0.7646 | 0.058* | |
C5 | 0.63843 (16) | 0.54125 (14) | 0.8307 (3) | 0.0562 (5) | |
H5 | 0.7034 | 0.5679 | 0.8762 | 0.067* | |
C6 | 0.30794 (16) | 0.64801 (10) | 0.5930 (3) | 0.0457 (4) | |
H6A | 0.2385 | 0.6504 | 0.4925 | 0.055* | |
H6B | 0.3576 | 0.6791 | 0.5517 | 0.055* | |
C7 | 0.30000 (19) | 0.68243 (11) | 0.7729 (3) | 0.0509 (5) | |
H7 | 0.2527 | 0.6592 | 0.8254 | 0.061* | |
C8 | 0.3551 (2) | 0.74283 (14) | 0.8607 (3) | 0.0640 (6) | |
H8A | 0.4031 | 0.7673 | 0.8115 | 0.077* | |
H8B | 0.3468 | 0.7618 | 0.9729 | 0.077* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0512 (2) | 0.04358 (19) | 0.0763 (2) | 0.000 | 0.02951 (16) | 0.000 |
O1 | 0.0922 (14) | 0.0556 (11) | 0.0888 (13) | −0.0055 (9) | 0.0312 (12) | 0.0044 (9) |
N1 | 0.0389 (8) | 0.0313 (7) | 0.0430 (8) | 0.0003 (6) | 0.0122 (6) | 0.0006 (6) |
C1 | 0.0375 (14) | 0.0427 (15) | 0.082 (2) | 0.000 | 0.0133 (14) | 0.000 |
C2 | 0.0392 (13) | 0.0351 (13) | 0.0433 (13) | 0.000 | 0.0135 (11) | 0.000 |
C3 | 0.0385 (9) | 0.0402 (9) | 0.0329 (8) | −0.0015 (7) | 0.0109 (7) | −0.0002 (7) |
C4 | 0.0459 (10) | 0.0509 (11) | 0.0466 (10) | −0.0100 (8) | 0.0124 (8) | −0.0048 (8) |
C5 | 0.0398 (10) | 0.0764 (13) | 0.0470 (10) | −0.0110 (10) | 0.0076 (8) | −0.0070 (9) |
C6 | 0.0497 (10) | 0.0306 (9) | 0.0526 (10) | 0.0022 (8) | 0.0120 (8) | 0.0076 (7) |
C7 | 0.0527 (12) | 0.0383 (10) | 0.0654 (13) | 0.0045 (8) | 0.0248 (10) | 0.0033 (8) |
C8 | 0.0748 (15) | 0.0484 (12) | 0.0691 (14) | −0.0005 (11) | 0.0248 (12) | −0.0055 (10) |
O1—H11 | 0.86 (1) | C3—C4 | 1.390 (3) |
O1—H12 | 0.85 (1) | C4—C5 | 1.379 (3) |
O1—H13 | 0.86 (1) | C4—H4 | 0.9300 |
N1—C2 | 1.339 (2) | C5—C5i | 1.392 (5) |
N1—C3 | 1.393 (2) | C5—H5 | 0.9300 |
N1—C6 | 1.480 (2) | C6—C7 | 1.487 (3) |
C1—C2 | 1.479 (4) | C6—H6A | 0.9700 |
C1—H1A | 0.9600 | C6—H6B | 0.9700 |
C1—H1B | 0.9600 | C7—C8 | 1.294 (3) |
C1—H1C | 0.9600 | C7—H7 | 0.9300 |
C2—N1i | 1.339 (2) | C8—H8A | 0.9300 |
C3—C3i | 1.387 (4) | C8—H8B | 0.9300 |
H11—O1—H12 | 108.7 (16) | C5—C4—C3 | 115.81 (19) |
H11—O1—H13 | 106.6 (16) | C5—C4—H4 | 122.1 |
H12—O1—H13 | 109.4 (17) | C3—C4—H4 | 122.1 |
C2—N1—C3 | 108.70 (15) | C4—C5—C5i | 122.17 (12) |
C2—N1—C6 | 126.45 (16) | C4—C5—H5 | 118.9 |
C3—N1—C6 | 124.84 (15) | C5i—C5—H5 | 118.9 |
C2—C1—H1A | 109.5 | N1—C6—C7 | 111.34 (15) |
C2—C1—H1B | 109.5 | N1—C6—H6A | 109.4 |
H1A—C1—H1B | 109.5 | C7—C6—H6A | 109.4 |
C2—C1—H1C | 109.5 | N1—C6—H6B | 109.4 |
H1A—C1—H1C | 109.5 | C7—C6—H6B | 109.4 |
H1B—C1—H1C | 109.5 | H6A—C6—H6B | 108.0 |
N1—C2—N1i | 109.3 (2) | C8—C7—C6 | 123.8 (2) |
N1—C2—C1 | 125.33 (11) | C8—C7—H7 | 118.1 |
N1i—C2—C1 | 125.33 (11) | C6—C7—H7 | 118.1 |
C3i—C3—C4 | 122.02 (12) | C7—C8—H8A | 120.0 |
C3i—C3—N1 | 106.63 (9) | C7—C8—H8B | 120.0 |
C4—C3—N1 | 131.31 (17) | H8A—C8—H8B | 120.0 |
C3—N1—C2—N1i | 0.3 (2) | C6—N1—C3—C4 | −2.1 (3) |
C6—N1—C2—N1i | 179.79 (12) | C3i—C3—C4—C5 | −0.5 (2) |
C3—N1—C2—C1 | −178.4 (2) | N1—C3—C4—C5 | −177.78 (17) |
C6—N1—C2—C1 | 1.0 (4) | C3—C4—C5—C5i | 0.5 (2) |
C2—N1—C3—C3i | −0.20 (15) | C2—N1—C6—C7 | 98.5 (2) |
C6—N1—C3—C3i | −179.67 (13) | C3—N1—C6—C7 | −82.1 (2) |
C2—N1—C3—C4 | 177.40 (19) | N1—C6—C7—C8 | 118.6 (2) |
Symmetry code: (i) x, −y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H11···Br1 | 0.86 (1) | 2.49 (1) | 3.351 (2) | 178 (2) |
O1—H13···O1ii | 0.86 (1) | 1.98 (1) | 2.822 (5) | 166 (4) |
O1—H12···O1i | 0.85 (1) | 1.97 (2) | 2.748 (4) | 152 (3) |
Symmetry codes: (i) x, −y+1, z; (ii) −x, y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C14H17N2+·Br−·2H2O |
Mr | 329.24 |
Crystal system, space group | Monoclinic, C2/m |
Temperature (K) | 295 |
a, b, c (Å) | 13.2888 (2), 16.8763 (2), 7.3897 (1) |
β (°) | 109.773 (1) |
V (Å3) | 1559.54 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.64 |
Crystal size (mm) | 0.4 × 0.3 × 0.2 |
Data collection | |
Diffractometer | Bruker APEXII diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.403, 0.590 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11870, 1851, 1497 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.085, 0.95 |
No. of reflections | 1851 |
No. of parameters | 103 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.31, −0.18 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H11···Br1 | 0.86 (1) | 2.49 (1) | 3.351 (2) | 178 (2) |
O1—H13···O1i | 0.86 (1) | 1.98 (1) | 2.822 (5) | 166 (4) |
O1—H12···O1ii | 0.85 (1) | 1.97 (2) | 2.748 (4) | 152 (3) |
Symmetry codes: (i) −x, y, −z+2; (ii) x, −y+1, z. |
Acknowledgements
We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.
References
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