3-Allyl-1-(3-cyano­phenyl­methyl­ene)-2-methyl-1H-benzoimidazol-3-ium bromide monohydrate

Xu, X.-B.; Fu, R.; Ye, Q.

doi:10.1107/S1600536807061867

organic compounds

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Volume 64| Part 1| January 2008| Page o109

https://doi.org/10.1107/S1600536807061867

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3-Allyl-1-(3-cyanophenylmethylene)-2-methyl-1H-benzoimidazol-3-ium bromide monohydrate

Xiong-Bin Xu,^a Rong Fu ^a and Qiong Ye ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: yeqiong@seu.edu.cn

(Received 9 October 2007; accepted 21 November 2007; online 6 December 2007)

In the title compound, C₁₉H₁₈N₃⁺·Br⁻·H₂O, the dihedral angle between the allyl group and the imidazole ring is 89.59 (14)°, while the dihedral angle between the cyanophenyl ring and the imidazole ring is 78.72 (7)°. O—H⋯Br hydrogen bonds form an infinite chain in the c-axis direction and C—H⋯Br and C—H⋯O interactions expand this chain into an infinite three-dimensional network.

Related literature

For related literature, see Aakeröy et al. (2005 ).

Experimental

Crystal data

C₁₉H₁₈N₃⁺·Br⁻·H₂O
M_r = 386.29
Monoclinic, P 2₁ /c
a = 13.4291 (18) Å
b = 15.6490 (17) Å
c = 9.0335 (14) Å
β = 104.048 (8)°
V = 1841.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.24 mm⁻¹
T = 293 (2) K
0.22 × 0.15 × 0.08 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.840, T_max = 1.000 (expected range = 0.702–0.836)
14149 measured reflections
4366 independent reflections
3365 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.111
S = 1.08
4366 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1⋯Br1	0.85	2.59	3.375 (2)	155
O1W—H2⋯Br1ⁱ	0.85	2.78	3.422 (3)	134
C6—H6A⋯Br1ⁱⁱ	0.93	3.21	3.939 (3)	137
C8—H8A⋯Br1ⁱⁱⁱ	0.96	2.94	3.767 (3)	145
C8—H8C⋯N3^iv	0.96	2.64	3.463 (4)	143
C13—H13A⋯O1W^v	0.93	2.50	3.359 (4)	154
C17—H17A⋯Br1^vi	0.97	2.89	3.843 (3)	168
C17—H17B⋯Br1ⁱⁱⁱ	0.97	2.91	3.862 (3)	167
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+1; (iii) -x+1, -y, -z; (iv) x, y, z-1; (v) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (vi) x-1, y, z-1.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1999 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807061867/kj2074sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807061867/kj2074Isup2.hkl

checkCIF report

Comment top

The title compound (Figure 1) was obtained by refluxing 3-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)benzonitrile and allyl bromide in THF. The X-ray diffraction experiment certified the successful synthesis of the title compound. The dihedral angle between the allyl groups and the imidazole ring is 89.59 (14)°, while the dihedral angle between the cyanobenzene ring and the imidazole ring is 78.72 (7)°. The twist of the allyl group (torsion N3—C17—C18=C19) is 5.1 (5)°. The O—H···Br H-bonds form an infinite chain in the c-direction and the C—H···Br and C—H···O interactions expand this chain into an infinite three-dimensional network (Figure 2). The interaction distances and angles are shown in Table.

Related literature top

For related literature, see Aakeröy et al. (2005).

Experimental top

The synthesis of 3-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl) benzonitrile has been reported by Aakeröy, et al. (2005). 2.48 g of this compound was dissolved in 30 ml THF and 3.7 g of allyl bromide (3-bromopropene) was added. The solution was stirred at 323 K for two days, after which a white solid appeared. This solid was filtered off and washed twice by acetone to get 1.90 g product (yield 64.7%). Colorless crystals of the title compound, suitable for X-ray diffraction, were obtained by evaporation of a solution in methanol and water.

Structure description top

For related literature, see Aakeröy et al. (2005).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 1999).

Figures top

	Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level
	Fig. 2. View of the crystal packing of the title compound down the a axis.

3-Allyl-1-(3-cyanophenylmethylene)-2-methyl-1H-benzoimidazol-3-ium bromide monohydrate top

Crystal data top

C₁₉H₁₈N₃⁺·Br⁻·H₂O	F(000) = 792
M_r = 386.29	D_x = 1.393 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4089 reflections
a = 13.4291 (18) Å	θ = 3.0–28.3°
b = 15.6490 (17) Å	µ = 2.24 mm⁻¹
c = 9.0335 (14) Å	T = 293 K
β = 104.048 (8)°	Prism, colorless
V = 1841.6 (4) Å³	0.22 × 0.15 × 0.08 mm
Z = 4

Data collection top

Rigaku Mercury2 diffractometer	4366 independent reflections
Radiation source: fine-focus sealed tube	3365 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.9°, θ_min = 2.7°
ω scan	h = −17→17
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −20→20
T_min = 0.840, T_max = 1.000	l = −8→11
14149 measured reflections

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0552P)² + 0.1803P] where P = (F_o² + 2F_c²)/3
4366 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₉H₁₈N₃⁺·Br⁻·H₂O	V = 1841.6 (4) Å³
M_r = 386.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.4291 (18) Å	µ = 2.24 mm⁻¹
b = 15.6490 (17) Å	T = 293 K
c = 9.0335 (14) Å	0.22 × 0.15 × 0.08 mm
β = 104.048 (8)°

Data collection top

Rigaku Mercury2 diffractometer	4366 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3365 reflections with I > 2σ(I)
T_min = 0.840, T_max = 1.000	R_int = 0.036
14149 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.08	Δρ_max = 0.32 e Å⁻³
4366 reflections	Δρ_min = −0.33 e Å⁻³
218 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.21740 (14)	0.01484 (13)	0.0889 (2)	0.0399 (4)
N2	0.13955 (16)	0.06050 (14)	−0.1380 (2)	0.0467 (5)
N3	0.4739 (2)	0.12165 (17)	0.8335 (3)	0.0710 (8)
C13	0.5074 (2)	0.1603 (2)	0.4691 (3)	0.0578 (7)
H13A	0.5544	0.1990	0.5246	0.069*
C16	0.4615 (2)	0.11908 (17)	0.7045 (4)	0.0553 (7)
C2	0.08324 (19)	0.09107 (16)	−0.0375 (3)	0.0441 (6)
C11	0.37725 (18)	0.05370 (16)	0.4585 (3)	0.0452 (6)
H11A	0.3372	0.0213	0.5081	0.054*
C7	0.13222 (18)	0.06166 (15)	0.1066 (3)	0.0419 (5)
C9	0.29401 (19)	−0.02289 (16)	0.2168 (3)	0.0441 (6)
H9A	0.3330	−0.0660	0.1779	0.053*
H9B	0.2591	−0.0507	0.2858	0.053*
C10	0.36673 (18)	0.04385 (15)	0.3033 (3)	0.0411 (5)
C6	0.0942 (2)	0.07708 (18)	0.2331 (3)	0.0513 (6)
H6A	0.1267	0.0566	0.3293	0.062*
C1	0.21926 (18)	0.01478 (16)	−0.0588 (3)	0.0432 (6)
C12	0.4477 (2)	0.11203 (16)	0.5407 (3)	0.0478 (6)
C3	−0.0059 (2)	0.13911 (17)	−0.0624 (4)	0.0560 (7)
H3A	−0.0386	0.1593	−0.1588	0.067*
C5	0.0052 (2)	0.12465 (17)	0.2082 (4)	0.0612 (8)
H5A	−0.0233	0.1367	0.2900	0.073*
C15	0.4277 (2)	0.09288 (18)	0.2320 (3)	0.0508 (6)
H15A	0.4216	0.0866	0.1279	0.061*
C8	0.2952 (2)	−0.0302 (2)	−0.1243 (3)	0.0585 (7)
H8A	0.2728	−0.0296	−0.2336	0.088*
H8B	0.3017	−0.0882	−0.0888	0.088*
H8C	0.3604	−0.0020	−0.0931	0.088*
C14	0.4973 (2)	0.1509 (2)	0.3143 (4)	0.0612 (8)
H14A	0.5374	0.1836	0.2652	0.073*
C4	−0.0434 (2)	0.15524 (19)	0.0631 (4)	0.0624 (8)
H4A	−0.1029	0.1875	0.0515	0.075*
C17	0.1160 (2)	0.0806 (2)	−0.3020 (3)	0.0597 (8)
H17A	0.0422	0.0852	−0.3401	0.072*
H17B	0.1394	0.0339	−0.3555	0.072*
C18	0.1641 (3)	0.1606 (3)	−0.3359 (4)	0.0743 (9)
H18A	0.1468	0.1784	−0.4372	0.089*
C19	0.2281 (3)	0.2095 (3)	−0.2405 (5)	0.0915 (12)
H19A	0.2481	0.1949	−0.1377	0.110*
H19B	0.2536	0.2588	−0.2753	0.110*
O1W	0.7083 (2)	0.25974 (19)	0.2290 (4)	0.1174 (12)
H1	0.7192	0.2206	0.2963	0.176*
H2	0.7528	0.2564	0.1764	0.176*
Br1	0.83295 (2)	0.126019 (17)	0.50549 (3)	0.04996 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0344 (10)	0.0447 (11)	0.0394 (12)	−0.0014 (8)	0.0065 (8)	−0.0018 (8)
N2	0.0428 (11)	0.0545 (13)	0.0395 (12)	0.0006 (10)	0.0034 (9)	−0.0039 (9)
N3	0.0726 (19)	0.085 (2)	0.0525 (17)	0.0022 (14)	0.0088 (14)	−0.0114 (13)
C13	0.0448 (14)	0.0614 (17)	0.0614 (19)	−0.0065 (14)	0.0014 (12)	−0.0066 (14)
C16	0.0478 (15)	0.0593 (17)	0.0553 (19)	0.0010 (13)	0.0058 (13)	−0.0084 (13)
C2	0.0380 (13)	0.0477 (14)	0.0454 (15)	−0.0015 (11)	0.0079 (10)	−0.0042 (11)
C11	0.0377 (12)	0.0482 (14)	0.0495 (15)	0.0033 (11)	0.0103 (11)	0.0050 (11)
C7	0.0376 (12)	0.0418 (13)	0.0463 (15)	−0.0028 (10)	0.0103 (10)	−0.0024 (10)
C9	0.0400 (12)	0.0416 (13)	0.0485 (15)	0.0012 (10)	0.0067 (11)	0.0047 (10)
C10	0.0365 (12)	0.0416 (13)	0.0434 (14)	0.0025 (10)	0.0062 (10)	0.0033 (10)
C6	0.0524 (15)	0.0555 (16)	0.0497 (16)	0.0002 (13)	0.0194 (12)	0.0003 (12)
C1	0.0359 (12)	0.0470 (14)	0.0446 (15)	−0.0051 (11)	0.0055 (10)	−0.0075 (11)
C12	0.0395 (13)	0.0525 (15)	0.0476 (16)	0.0054 (11)	0.0031 (11)	−0.0011 (11)
C3	0.0459 (15)	0.0548 (17)	0.0629 (19)	0.0037 (12)	0.0045 (13)	0.0010 (13)
C5	0.0600 (18)	0.0604 (18)	0.072 (2)	0.0020 (15)	0.0332 (16)	−0.0074 (14)
C15	0.0515 (15)	0.0549 (15)	0.0460 (16)	−0.0034 (13)	0.0116 (12)	0.0048 (12)
C8	0.0503 (15)	0.075 (2)	0.0502 (17)	0.0063 (14)	0.0124 (13)	−0.0138 (14)
C14	0.0550 (17)	0.0614 (17)	0.068 (2)	−0.0157 (15)	0.0154 (14)	0.0063 (15)
C4	0.0504 (16)	0.0529 (16)	0.086 (2)	0.0124 (14)	0.0196 (15)	−0.0016 (16)
C17	0.0580 (17)	0.077 (2)	0.0386 (16)	0.0116 (16)	0.0006 (12)	−0.0045 (13)
C18	0.084 (2)	0.080 (2)	0.062 (2)	0.016 (2)	0.0218 (18)	0.0164 (18)
C19	0.094 (3)	0.071 (2)	0.118 (3)	0.006 (2)	0.042 (3)	0.021 (2)
O1W	0.0692 (16)	0.126 (2)	0.153 (3)	0.0065 (16)	0.0181 (17)	0.084 (2)
Br1	0.05534 (19)	0.05266 (18)	0.04170 (18)	−0.00159 (12)	0.01142 (12)	0.00224 (11)

Geometric parameters (Å, º) top

N1—C1	1.340 (3)	C6—H6A	0.9300
N1—C7	1.400 (3)	C1—C8	1.476 (4)
N1—C9	1.472 (3)	C3—C4	1.371 (4)
N2—C1	1.341 (3)	C3—H3A	0.9300
N2—C2	1.400 (3)	C5—C4	1.399 (5)
N2—C17	1.471 (3)	C5—H5A	0.9300
N3—C16	1.137 (4)	C15—C14	1.383 (4)
C13—C12	1.372 (4)	C15—H15A	0.9300
C13—C14	1.379 (4)	C8—H8A	0.9600
C13—H13A	0.9300	C8—H8B	0.9600
C16—C12	1.450 (4)	C8—H8C	0.9600
C2—C7	1.387 (4)	C14—H14A	0.9300
C2—C3	1.385 (4)	C4—H4A	0.9300
C11—C10	1.383 (3)	C17—C18	1.475 (5)
C11—C12	1.392 (4)	C17—H17A	0.9700
C11—H11A	0.9300	C17—H17B	0.9700
C7—C6	1.381 (3)	C18—C19	1.306 (5)
C9—C10	1.512 (3)	C18—H18A	0.9300
C9—H9A	0.9700	C19—H19A	0.9300
C9—H9B	0.9700	C19—H19B	0.9300
C10—C15	1.389 (4)	O1W—H1	0.8499
C6—C5	1.380 (4)	O1W—H2	0.8502

C1—N1—C7	109.1 (2)	C11—C12—C16	119.8 (3)
C1—N1—C9	127.1 (2)	C4—C3—C2	116.2 (3)
C7—N1—C9	123.7 (2)	C4—C3—H3A	121.9
C1—N2—C2	108.8 (2)	C2—C3—H3A	121.9
C1—N2—C17	126.9 (2)	C6—C5—C4	121.7 (3)
C2—N2—C17	124.2 (2)	C6—C5—H5A	119.1
C12—C13—C14	119.6 (3)	C4—C5—H5A	119.1
C12—C13—H13A	120.2	C14—C15—C10	120.7 (3)
C14—C13—H13A	120.2	C14—C15—H15A	119.6
N3—C16—C12	177.5 (3)	C10—C15—H15A	119.6
C7—C2—C3	121.8 (2)	C1—C8—H8A	109.5
C7—C2—N2	106.7 (2)	C1—C8—H8B	109.5
C3—C2—N2	131.5 (2)	H8A—C8—H8B	109.5
C10—C11—C12	120.2 (2)	C1—C8—H8C	109.5
C10—C11—H11A	119.9	H8A—C8—H8C	109.5
C12—C11—H11A	119.9	H8B—C8—H8C	109.5
C2—C7—C6	122.2 (2)	C15—C14—C13	120.1 (3)
C2—C7—N1	106.3 (2)	C15—C14—H14A	119.9
C6—C7—N1	131.5 (2)	C13—C14—H14A	119.9
N1—C9—C10	111.70 (19)	C3—C4—C5	122.1 (3)
N1—C9—H9A	109.3	C3—C4—H4A	119.0
C10—C9—H9A	109.3	C5—C4—H4A	119.0
N1—C9—H9B	109.3	N2—C17—C18	113.1 (3)
C10—C9—H9B	109.3	N2—C17—H17A	109.0
H9A—C9—H9B	107.9	C18—C17—H17A	109.0
C11—C10—C15	118.8 (2)	N2—C17—H17B	109.0
C11—C10—C9	119.7 (2)	C18—C17—H17B	109.0
C15—C10—C9	121.4 (2)	H17A—C17—H17B	107.8
C7—C6—C5	116.0 (3)	C19—C18—C17	127.6 (3)
C7—C6—H6A	122.0	C19—C18—H18A	116.2
C5—C6—H6A	122.0	C17—C18—H18A	116.2
N2—C1—N1	109.0 (2)	C18—C19—H19A	120.0
N2—C1—C8	125.4 (2)	C18—C19—H19B	120.0
N1—C1—C8	125.5 (2)	H19A—C19—H19B	120.0
C13—C12—C11	120.5 (3)	H1—O1W—H2	109.5
C13—C12—C16	119.6 (3)

C1—N2—C2—C7	−0.1 (3)	C2—N2—C1—C8	178.2 (3)
C17—N2—C2—C7	−177.1 (2)	C17—N2—C1—C8	−5.0 (4)
C1—N2—C2—C3	−178.3 (3)	C7—N1—C1—N2	0.8 (3)
C17—N2—C2—C3	4.8 (4)	C9—N1—C1—N2	−175.9 (2)
C3—C2—C7—C6	1.2 (4)	C7—N1—C1—C8	−177.8 (2)
N2—C2—C7—C6	−177.2 (2)	C9—N1—C1—C8	5.6 (4)
C3—C2—C7—N1	178.9 (2)	C14—C13—C12—C11	0.1 (4)
N2—C2—C7—N1	0.6 (3)	C14—C13—C12—C16	177.2 (3)
C1—N1—C7—C2	−0.8 (3)	C10—C11—C12—C13	0.0 (4)
C9—N1—C7—C2	175.9 (2)	C10—C11—C12—C16	−177.2 (2)
C1—N1—C7—C6	176.6 (3)	C7—C2—C3—C4	−0.5 (4)
C9—N1—C7—C6	−6.6 (4)	N2—C2—C3—C4	177.4 (3)
C1—N1—C9—C10	99.8 (3)	C7—C6—C5—C4	0.0 (4)
C7—N1—C9—C10	−76.3 (3)	C11—C10—C15—C14	−0.3 (4)
C12—C11—C10—C15	0.2 (4)	C9—C10—C15—C14	−177.0 (3)
C12—C11—C10—C9	176.8 (2)	C10—C15—C14—C13	0.4 (5)
N1—C9—C10—C11	123.7 (2)	C12—C13—C14—C15	−0.3 (5)
N1—C9—C10—C15	−59.7 (3)	C2—C3—C4—C5	−0.4 (4)
C2—C7—C6—C5	−0.9 (4)	C6—C5—C4—C3	0.6 (5)
N1—C7—C6—C5	−178.0 (3)	C1—N2—C17—C18	−89.6 (3)
C2—N2—C1—N1	−0.4 (3)	C2—N2—C17—C18	86.7 (3)
C17—N2—C1—N1	176.5 (2)	N2—C17—C18—C19	5.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···Br1	0.85	2.59	3.375 (2)	155
O1W—H2···Br1ⁱ	0.85	2.78	3.422 (3)	134
C6—H6A···Br1ⁱⁱ	0.93	3.21	3.939 (3)	137
C8—H8A···Br1ⁱⁱⁱ	0.96	2.94	3.767 (3)	145
C8—H8C···N3^iv	0.96	2.64	3.463 (4)	143
C13—H13A···O1W^v	0.93	2.50	3.359 (4)	154
C17—H17A···Br1^vi	0.97	2.89	3.843 (3)	168
C17—H17B···Br1ⁱⁱⁱ	0.97	2.91	3.862 (3)	167

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y, −z+1; (iii) −x+1, −y, −z; (iv) x, y, z−1; (v) x, −y+1/2, z+1/2; (vi) x−1, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈N₃⁺·Br⁻·H₂O
M_r	386.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.4291 (18), 15.6490 (17), 9.0335 (14)
β (°)	104.048 (8)
V (Å³)	1841.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.24
Crystal size (mm)	0.22 × 0.15 × 0.08

Data collection
Diffractometer	Rigaku Mercury2
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.840, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14149, 4366, 3365
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.111, 1.08
No. of reflections	4366
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.33

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···Br1	0.85	2.59	3.375 (2)	154.5
O1W—H2···Br1ⁱ	0.85	2.78	3.422 (3)	133.5
C6—H6A···Br1ⁱⁱ	0.93	3.21	3.939 (3)	136.8
C8—H8A···Br1ⁱⁱⁱ	0.96	2.94	3.767 (3)	145.3
C8—H8C···N3^iv	0.96	2.64	3.463 (4)	143.4
C13—H13A···O1W^v	0.93	2.50	3.359 (4)	153.9
C17—H17A···Br1^vi	0.97	2.89	3.843 (3)	168.0
C17—H17B···Br1ⁱⁱⁱ	0.97	2.91	3.862 (3)	166.6

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y, −z+1; (iii) −x+1, −y, −z; (iv) x, y, z−1; (v) x, −y+1/2, z+1/2; (vi) x−1, y, z−1.

Acknowledgements

This work was supported by a Start-up Grant from SEU to YQ.

References

Aakeröy, C. B., Desper, J. & Urbina, J. F. (2005). Cryst. Growth Des. 5, 1283–1293. Google Scholar
Rigaku (2005). CrystalClear. Version 1.4.0. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1999). SHELXTL/PC. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-Allyl-1-(3-cyano­phenyl­methyl­ene)-2-methyl-1H-benzoimidazol-3-ium bromide monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Allyl-1-(3-cyanophenylmethylene)-2-methyl-1H-benzoimidazol-3-ium bromide monohydrate