3-Allyl-1-(2-cyano-benz-yl)-2-methyl-benzimidazol-3-ium bromide.

In the title compound, C(19)H(18)N(3) (+)·Br(-), both the allyl and cyano-phenyl groups are approximately perpendicular to the central benzimidazole unit, making dihedral angles of 89.7 (2) and 85.09 (13)°, respectively. The crystal packing is dominated by C-H⋯Br inter-actions, with each anion inter-acting with five neighboring cations.

Related literature

For olefin–copper coordination compounds, see: Ye et al. (2005 ▶). For the synthesis, see: Aakeroy et al. (2005 ▶). For a similar structure, see: Herrmann et al. (1997 ▶).

Experimental

Crystal data

C19H18N3 +·Br−

M = 368.27

Triclinic,

a = 9.123 (5) Å

b = 10.100 (4) Å

c = 10.520 (4) Å

α = 98.924 (2)°

β = 108.490 (18)°

γ = 102.851 (11)°

V = 869.2 (7) Å3

Z = 2

Mo Kα radiation

μ = 2.37 mm−1

T = 293 (2) K

0.15 × 0.10 × 0.07 mm

Data collection

Rigaku Mercury2 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.872, T max = 1.000 (expected range = 0.739–0.847)

9212 measured reflections

4233 independent reflections

3434 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.143

S = 0.92

4233 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.40 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807060874/fl2171sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807060874/fl2171Isup2.hkl

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

C19H18N3+·Br–	Z = 2
Mr = 368.27	F000 = 376
Triclinic, P1	Dx = 1.407 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.123 (5) Å	Cell parameters from 2405 reflections
b = 10.100 (4) Å	θ = 3.2–28.2º
c = 10.520 (4) Å	µ = 2.37 mm−1
α = 98.924 (2)º	T = 293 (2) K
β = 108.490 (18)º	Prism, colorless
γ = 102.851 (11)º	0.15 × 0.10 × 0.07 mm
V = 869.2 (7) Å3

Rigaku Mercury2 CCD diffractometer	4233 independent reflections
Radiation source: fine-focus sealed tube	3434 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
Detector resolution: 13.6612 pixels mm-1	θmax = 28.3º
T = 293(2) K	θmin = 2.6º
CCD_Profile_fitting scans	h = −12→12
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −13→13
Tmin = 0.872, Tmax = 1.000	l = −13→13
9212 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.143	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max = 0.001
4233 reflections	Δρmax = 0.38 e Å−3
209 parameters	Δρmin = −0.40 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
Br1	0.28828 (4)	0.88178 (3)	0.19130 (3)	0.04548 (14)
N1	−0.1709 (5)	0.4159 (4)	0.1763 (4)	0.0776 (11)
N4	−0.1796 (3)	0.1568 (3)	0.4110 (3)	0.0405 (6)
N6	−0.0363 (3)	0.1395 (3)	0.2796 (2)	0.0363 (5)
C2	−0.3282 (6)	0.3088 (6)	0.4888 (5)	0.0740 (12)
H2A	−0.4050	0.3187	0.5274	0.089*
C3	0.3772 (5)	0.3551 (5)	0.1240 (5)	0.0682 (11)
H3A	0.4730	0.3470	0.1146	0.082*
C4	0.3403 (5)	0.4803 (5)	0.1239 (5)	0.0705 (12)
H4A	0.4108	0.5561	0.1133	0.085*
C6	−0.2509 (8)	0.4191 (6)	0.4705 (6)	0.0950 (17)
H6A	−0.1700	0.4139	0.4312	0.114*
H6B	−0.2708	0.5071	0.4951	0.114*
C8	−0.3359 (4)	0.0951 (5)	0.1562 (4)	0.0572 (9)
H8A	−0.4256	0.0966	0.1849	0.086*
H8B	−0.3539	0.0031	0.1023	0.086*
H8C	−0.3255	0.1618	0.1015	0.086*
C11	−0.0554 (5)	0.3978 (4)	0.1660 (4)	0.0568 (9)
C13	0.1989 (6)	0.4936 (4)	0.1394 (4)	0.0619 (10)
H13A	0.1752	0.5787	0.1416	0.074*
C14	−0.3138 (4)	0.1649 (4)	0.4574 (4)	0.0530 (9)
H14A	−0.2991	0.1291	0.5396	0.064*
H14B	−0.4139	0.1050	0.3861	0.064*
C17	0.2104 (5)	0.2193 (4)	0.6974 (4)	0.0584 (9)
H17A	0.2618	0.2399	0.7929	0.070*
C18	0.3013 (4)	0.2017 (4)	0.6138 (4)	0.0562 (9)
H18A	0.4098	0.2076	0.6551	0.067*
C20	0.2714 (4)	0.2415 (4)	0.1381 (4)	0.0525 (8)
H20A	0.2975	0.1576	0.1383	0.063*
C22	0.0487 (4)	0.2073 (4)	0.6436 (3)	0.0499 (8)
H22A	−0.0116	0.2162	0.6993	0.060*
C26	0.2329 (4)	0.1757 (4)	0.4708 (3)	0.0471 (7)
H26A	0.2925	0.1642	0.4149	0.056*
C29	0.0100 (4)	0.1207 (3)	0.1566 (3)	0.0395 (6)
H29A	−0.0867	0.0945	0.0741	0.047*
H29B	0.0584	0.0444	0.1556	0.047*
C30	0.0921 (4)	0.3786 (4)	0.1518 (3)	0.0470 (7)
C32	−0.1857 (4)	0.1316 (3)	0.2799 (3)	0.0398 (6)
C34	−0.0194 (4)	0.1809 (3)	0.5002 (3)	0.0390 (6)
C36	0.0703 (3)	0.1677 (3)	0.4164 (3)	0.0375 (6)
C38	0.1274 (4)	0.2503 (3)	0.1520 (3)	0.0391 (6)

	U11	U22	U33	U12	U13	U23
Br1	0.0481 (2)	0.0486 (2)	0.0420 (2)	0.01498 (14)	0.01626 (15)	0.01637 (14)
N1	0.092 (3)	0.078 (2)	0.094 (3)	0.050 (2)	0.051 (2)	0.034 (2)
N4	0.0351 (13)	0.0511 (15)	0.0358 (13)	0.0106 (11)	0.0139 (10)	0.0129 (11)
N6	0.0338 (12)	0.0422 (13)	0.0345 (12)	0.0112 (10)	0.0135 (10)	0.0118 (10)
C2	0.062 (3)	0.086 (3)	0.079 (3)	0.025 (2)	0.034 (2)	0.011 (2)
C3	0.054 (2)	0.082 (3)	0.076 (3)	0.011 (2)	0.032 (2)	0.032 (2)
C4	0.068 (3)	0.063 (3)	0.069 (3)	−0.008 (2)	0.022 (2)	0.028 (2)
C6	0.117 (5)	0.085 (4)	0.096 (4)	0.044 (3)	0.050 (4)	0.015 (3)
C8	0.0373 (17)	0.084 (3)	0.0443 (19)	0.0105 (17)	0.0088 (14)	0.0216 (18)
C11	0.071 (2)	0.055 (2)	0.061 (2)	0.0308 (18)	0.0323 (19)	0.0238 (17)
C13	0.079 (3)	0.0445 (19)	0.062 (2)	0.0124 (18)	0.026 (2)	0.0195 (17)
C14	0.0428 (18)	0.076 (2)	0.0447 (19)	0.0134 (16)	0.0240 (15)	0.0161 (17)
C17	0.055 (2)	0.071 (2)	0.0361 (18)	0.0108 (17)	0.0047 (15)	0.0113 (16)
C18	0.0442 (19)	0.066 (2)	0.050 (2)	0.0148 (16)	0.0039 (15)	0.0172 (17)
C20	0.0500 (19)	0.059 (2)	0.057 (2)	0.0203 (16)	0.0238 (16)	0.0241 (17)
C22	0.055 (2)	0.0531 (19)	0.0370 (16)	0.0115 (15)	0.0142 (14)	0.0107 (14)
C26	0.0394 (16)	0.0554 (19)	0.0463 (18)	0.0166 (14)	0.0118 (14)	0.0158 (15)
C29	0.0415 (15)	0.0431 (16)	0.0354 (15)	0.0120 (12)	0.0161 (12)	0.0100 (12)
C30	0.0554 (19)	0.0478 (18)	0.0404 (17)	0.0164 (14)	0.0184 (15)	0.0143 (14)
C32	0.0357 (14)	0.0451 (16)	0.0380 (15)	0.0087 (12)	0.0117 (12)	0.0164 (12)
C34	0.0389 (15)	0.0416 (15)	0.0342 (15)	0.0108 (12)	0.0106 (12)	0.0102 (12)
C36	0.0364 (14)	0.0368 (14)	0.0375 (15)	0.0103 (11)	0.0089 (12)	0.0143 (12)
C38	0.0415 (15)	0.0428 (16)	0.0332 (14)	0.0121 (12)	0.0123 (12)	0.0130 (12)

N1—C11	1.144 (5)	C11—C30	1.451 (5)
N4—C32	1.344 (4)	C13—C30	1.393 (5)
N4—C34	1.406 (4)	C13—H13A	0.9300
N4—C14	1.468 (4)	C14—H14A	0.9700
N6—C32	1.348 (4)	C14—H14B	0.9700
N6—C36	1.400 (4)	C17—C22	1.371 (5)
N6—C29	1.482 (4)	C17—C18	1.405 (6)
C2—C6	1.256 (7)	C17—H17A	0.9300
C2—C14	1.484 (7)	C18—C26	1.389 (5)
C2—H2A	0.9300	C18—H18A	0.9300
C3—C4	1.379 (7)	C20—C38	1.388 (5)
C3—C20	1.387 (5)	C20—H20A	0.9300
C3—H3A	0.9300	C22—C34	1.392 (4)
C4—C13	1.383 (6)	C22—H22A	0.9300
C4—H4A	0.9300	C26—C36	1.389 (4)
C6—H6A	0.9600	C26—H26A	0.9300
C6—H6B	0.9600	C29—C38	1.514 (4)
C8—C32	1.484 (4)	C29—H29A	0.9700
C8—H8A	0.9600	C29—H29B	0.9700
C8—H8B	0.9600	C30—C38	1.403 (5)
C8—H8C	0.9600	C34—C36	1.391 (4)
C32—N4—C34	108.8 (3)	C22—C17—H17A	118.8
C32—N4—C14	126.9 (3)	C18—C17—H17A	118.8
C34—N4—C14	124.3 (3)	C26—C18—C17	121.6 (3)
C32—N6—C36	108.6 (2)	C26—C18—H18A	119.2
C32—N6—C29	126.6 (2)	C17—C18—H18A	119.2
C36—N6—C29	124.8 (2)	C3—C20—C38	121.4 (4)
C6—C2—C14	128.9 (5)	C3—C20—H20A	119.3
C6—C2—H2A	115.5	C38—C20—H20A	119.3
C14—C2—H2A	115.5	C17—C22—C34	115.8 (3)
C4—C3—C20	120.0 (4)	C17—C22—H22A	122.1
C4—C3—H3A	120.0	C34—C22—H22A	122.1
C20—C3—H3A	120.0	C36—C26—C18	116.0 (3)
C3—C4—C13	120.3 (3)	C36—C26—H26A	122.0
C3—C4—H4A	119.9	C18—C26—H26A	122.0
C13—C4—H4A	119.9	N6—C29—C38	113.6 (2)
C2—C6—H6A	118.5	N6—C29—H29A	108.9
C2—C6—H6B	121.6	C38—C29—H29A	108.9
H6A—C6—H6B	120.0	N6—C29—H29B	108.9
C32—C8—H8A	109.5	C38—C29—H29B	108.9
C32—C8—H8B	109.5	H29A—C29—H29B	107.7
H8A—C8—H8B	109.5	C13—C30—C38	121.1 (3)
C32—C8—H8C	109.5	C13—C30—C11	117.2 (3)
H8A—C8—H8C	109.5	C38—C30—C11	121.7 (3)
H8B—C8—H8C	109.5	N4—C32—N6	109.3 (3)
N1—C11—C30	178.4 (4)	N4—C32—C8	124.5 (3)
C4—C13—C30	119.5 (4)	N6—C32—C8	126.2 (3)
C4—C13—H13A	120.3	C36—C34—C22	122.4 (3)
C30—C13—H13A	120.3	C36—C34—N4	106.4 (3)
N4—C14—C2	113.6 (3)	C22—C34—N4	131.2 (3)
N4—C14—H14A	108.8	C26—C36—C34	121.7 (3)
C2—C14—H14A	108.8	C26—C36—N6	131.3 (3)
N4—C14—H14B	108.8	C34—C36—N6	106.9 (2)
C2—C14—H14B	108.8	C20—C38—C30	117.8 (3)
H14A—C14—H14B	107.7	C20—C38—C29	119.5 (3)
C22—C17—C18	122.4 (3)	C30—C38—C29	122.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Br1	0.93	2.91	3.738 (4)	149
C14—H14A···Br1i	0.97	2.82	3.740 (3)	158
C20—H20A···Br1ii	0.93	2.91	3.787 (4)	158
C29—H29A···Br1iii	0.97	2.90	3.798 (3)	155
C29—H29B···Br1ii	0.97	2.91	3.848 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Br1	0.93	2.91	3.738 (4)	149
C14—H14A⋯Br1i	0.97	2.82	3.740 (3)	158
C20—H20A⋯Br1ii	0.93	2.91	3.787 (4)	158
C29—H29A⋯Br1iii	0.97	2.90	3.798 (3)	155
C29—H29B⋯Br1ii	0.97	2.91	3.848 (3)	164

Symmetry codes: (i) ; (ii) ; (iii) .