1,3-Diallyl-2-methyl-benzimidazolium bromide dihydrate.

The bonds in the five-membered ring of the title hydrated salt, C(14)H(17)N(2) (+)·Br(-)·2H(2)O, are delocalized. The cation lies on a special position of m site symmetry such that the mirror plane passes through the imidazol-yl-methyl bond and is perpendicular to the plane of the cation. The anion lies on another special position of 2 site symmetry. The anion and uncoordinated water mol-ecule 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 crystal structure of 1,3-diallyl­benzimidazolium bromide, see: Holtgrewe 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

C14H17N2 +·Br−·2H2O

M = 329.24

Monoclinic,

a = 13.2888 (2) Å

b = 16.8763 (2) Å

c = 7.3897 (1) Å

β = 109.773 (1)°

V = 1559.54 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.64 mm−1

T = 295 K

0.4 × 0.3 × 0.2 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.403, T max = 0.590

11870 measured reflections

1851 independent reflections

1497 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.085

S = 0.95

1851 reflections

103 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.18 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034175/sj2636sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034175/sj2636Isup2.hkl

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

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	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

	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)

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)

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) .