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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o23
https://doi.org/10.1107/S1600536807060874

3-Allyl-1-(2-cyano­benz­yl)-2-methyl­benzimidazol-3-ium bromide

Xiong-Bin Xua and Qiong Yea*

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

(Received 13 October 2007; accepted 19 November 2007; online 6 December 2007)

In the title compound, C19H18N3+·Br−, both the allyl and cyano­phenyl 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 inter­actions, with each anion inter­acting with five neighboring cations.

Related literature

For olefin–copper coordination compounds, see: Ye et al. (2005[Ye, Q., Wang, X.-S., Zhao, H. & Xiong, R.-G. (2005). Chem. Soc. Rev. 34, 208-225.]). For the synthesis, see: Aakeroy et al. (2005[Aakeroy, C. B., Desper, J. & &Urbina, J. F. (2005). Cryst. Growth Des. 5, 1283-1293.]). For a similar structure, see: Herrmann et al. (1997[Herrmann, W. A., Goossen, L. J., Artus, G. R. J. & Kocher, C. (1997). Organometallics, 16, 2472-2474.]).

[Scheme 1]

Experimental

Crystal data

  • C19H18N3+·Br−

  • Mr = 368.27

  • Triclinic, [P \overline 1]

  • 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[Rigaku (2005). CrystalClear. Version 1.4.0. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.872, Tmax = 1.000 (expected range = 0.739–0.847)

  • 9212 measured reflections

  • 4233 independent reflections

  • 3434 reflections with I > 2σ(I)

  • Rint = 0.035
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 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

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) -x, -y+1, -z+1; (ii) x, y-1, z; (iii) -x, -y+1, -z.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Version 1.4.0. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Sheldrick, 1999[Sheldrick, G. M. (1999). SHELXTL/PC. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807060874/fl2171Isup2.hkl

checkCIF report


Comment top

It has been almost a century since the discovery of olefin- copper coordination compounds. We are interested in obtaining stable olefin- copper(I) coordination compounds under solvothermal conditions since these compounds display novel cluster structures and interesting physical properties such as fluorescence, SHG and ferroelectric(Ye et al. (2005)). The title compound (Fig 1) was synthesized as part of this project. No unexpected bond distances and angles were found in (I). Both the allyl and cyano-phenyl groups are approximately perpendicular to the central benzimidazole moiety with dihedral angles of 89.72 (23)° and 85.09 (13)° respectively such that the phenyl ring and the olefin moeity are almost parallel to one another in a conformation similar to that found by Herrmann et al. (1997). Thus, the molecule could adopt an end-to-head or parallel packing mode to form tight stacking. However, no π-π interactions are found. Crystal packing is dominated by C—H···Br interactions with each anion cation interacting with five neighboring cations.

Related literature top

For lefin–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 top

2-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl) benzonitrile (2.48 g) synthesized according to the procedure reported by (Aakeroy, et al.(2005) was dissolved in THF (30 ml) and allyl bromide;3- bromopropene (3.7 g) was added.The solution was stirred at 50° C for two days. The resulting white solid resultant was filterered out and washed twice with acetone to get 1.94 g of (I), (yield 66.7%). Colorless crystals suitable for X-ray diffraction were obtained by evaporation from methanol/water.

Refinement top

Positional parameters of all the H atoms were calculated geometrically and were allowed to ride on the C atoms to which they are bonded, with Uiso(H) = 1.2Ueq.

Structure description top

It has been almost a century since the discovery of olefin- copper coordination compounds. We are interested in obtaining stable olefin- copper(I) coordination compounds under solvothermal conditions since these compounds display novel cluster structures and interesting physical properties such as fluorescence, SHG and ferroelectric(Ye et al. (2005)). The title compound (Fig 1) was synthesized as part of this project. No unexpected bond distances and angles were found in (I). Both the allyl and cyano-phenyl groups are approximately perpendicular to the central benzimidazole moiety with dihedral angles of 89.72 (23)° and 85.09 (13)° respectively such that the phenyl ring and the olefin moeity are almost parallel to one another in a conformation similar to that found by Herrmann et al. (1997). Thus, the molecule could adopt an end-to-head or parallel packing mode to form tight stacking. However, no π-π interactions are found. Crystal packing is dominated by C—H···Br interactions with each anion cation interacting with five neighboring cations.

For lefin–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).

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
[Figure 1] Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level
[Figure 2] Fig. 2. Packing and cell box view of the title compound.
3-Allyl-1-(2-cyanobenzyl)-2-methylbenzimidazol-3-ium bromide top
Crystal data top
C19H18N3+·Br−Z = 2
Mr = 368.27F(000) = 376
Triclinic, P1Dx = 1.407 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.123 (5) ÅCell parameters from 2405 reflections
b = 10.100 (4) Åθ = 3.2–28.2°
c = 10.520 (4) ŵ = 2.37 mm−1
α = 98.924 (2)°T = 293 K
β = 108.490 (18)°Prism, colorless
γ = 102.851 (11)°0.15 × 0.10 × 0.07 mm
V = 869.2 (7) Å3
Data collection top
Rigaku Mercury2 CCD
diffractometer		4233 independent reflections
Radiation source: fine-focus sealed tube3434 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 13.6612 pixels mm-1θmax = 28.3°, θmin = 2.6°
CCD_Profile_fitting scansh = −12→12
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −13→13
Tmin = 0.872, Tmax = 1.000l = −13→13
9212 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
4233 reflections(Δ/σ)max = 0.001
209 parametersΔρmax = 0.38 e Å−3
0 restraintsΔρmin = −0.40 e Å−3
Crystal data top
C19H18N3+·Br−γ = 102.851 (11)°
Mr = 368.27V = 869.2 (7) Å3
Triclinic, P1Z = 2
a = 9.123 (5) ÅMo Kα radiation
b = 10.100 (4) ŵ = 2.37 mm−1
c = 10.520 (4) ÅT = 293 K
α = 98.924 (2)°0.15 × 0.10 × 0.07 mm
β = 108.490 (18)°
Data collection top
Rigaku Mercury2 CCD
diffractometer		4233 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		3434 reflections with I > 2σ(I)
Tmin = 0.872, Tmax = 1.000Rint = 0.035
9212 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 0.92Δρmax = 0.38 e Å−3
4233 reflectionsΔρmin = −0.40 e Å−3
209 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
xyzUiso*/Ueq
Br10.28828 (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−0.40500.31870.52740.089*
C30.3772 (5)0.3551 (5)0.1240 (5)0.0682 (11)
H3A0.47300.34700.11460.082*
C40.3403 (5)0.4803 (5)0.1239 (5)0.0705 (12)
H4A0.41080.55610.11330.085*
C6−0.2509 (8)0.4191 (6)0.4705 (6)0.0950 (17)
H6A−0.17000.41390.43120.114*
H6B−0.27080.50710.49510.114*
C8−0.3359 (4)0.0951 (5)0.1562 (4)0.0572 (9)
H8A−0.42560.09660.18490.086*
H8B−0.35390.00310.10230.086*
H8C−0.32550.16180.10150.086*
C11−0.0554 (5)0.3978 (4)0.1660 (4)0.0568 (9)
C130.1989 (6)0.4936 (4)0.1394 (4)0.0619 (10)
H13A0.17520.57870.14160.074*
C14−0.3138 (4)0.1649 (4)0.4574 (4)0.0530 (9)
H14A−0.29910.12910.53960.064*
H14B−0.41390.10500.38610.064*
C170.2104 (5)0.2193 (4)0.6974 (4)0.0584 (9)
H17A0.26180.23990.79290.070*
C180.3013 (4)0.2017 (4)0.6138 (4)0.0562 (9)
H18A0.40980.20760.65510.067*
C200.2714 (4)0.2415 (4)0.1381 (4)0.0525 (8)
H20A0.29750.15760.13830.063*
C220.0487 (4)0.2073 (4)0.6436 (3)0.0499 (8)
H22A−0.01160.21620.69930.060*
C260.2329 (4)0.1757 (4)0.4708 (3)0.0471 (7)
H26A0.29250.16420.41490.056*
C290.0100 (4)0.1207 (3)0.1566 (3)0.0395 (6)
H29A−0.08670.09450.07410.047*
H29B0.05840.04440.15560.047*
C300.0921 (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)
C360.0703 (3)0.1677 (3)0.4164 (3)0.0375 (6)
C380.1274 (4)0.2503 (3)0.1520 (3)0.0391 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0481 (2)0.0486 (2)0.0420 (2)0.01498 (14)0.01626 (15)0.01637 (14)
N10.092 (3)0.078 (2)0.094 (3)0.050 (2)0.051 (2)0.034 (2)
N40.0351 (13)0.0511 (15)0.0358 (13)0.0106 (11)0.0139 (10)0.0129 (11)
N60.0338 (12)0.0422 (13)0.0345 (12)0.0112 (10)0.0135 (10)0.0118 (10)
C20.062 (3)0.086 (3)0.079 (3)0.025 (2)0.034 (2)0.011 (2)
C30.054 (2)0.082 (3)0.076 (3)0.011 (2)0.032 (2)0.032 (2)
C40.068 (3)0.063 (3)0.069 (3)−0.008 (2)0.022 (2)0.028 (2)
C60.117 (5)0.085 (4)0.096 (4)0.044 (3)0.050 (4)0.015 (3)
C80.0373 (17)0.084 (3)0.0443 (19)0.0105 (17)0.0088 (14)0.0216 (18)
C110.071 (2)0.055 (2)0.061 (2)0.0308 (18)0.0323 (19)0.0238 (17)
C130.079 (3)0.0445 (19)0.062 (2)0.0124 (18)0.026 (2)0.0195 (17)
C140.0428 (18)0.076 (2)0.0447 (19)0.0134 (16)0.0240 (15)0.0161 (17)
C170.055 (2)0.071 (2)0.0361 (18)0.0108 (17)0.0047 (15)0.0113 (16)
C180.0442 (19)0.066 (2)0.050 (2)0.0148 (16)0.0039 (15)0.0172 (17)
C200.0500 (19)0.059 (2)0.057 (2)0.0203 (16)0.0238 (16)0.0241 (17)
C220.055 (2)0.0531 (19)0.0370 (16)0.0115 (15)0.0142 (14)0.0107 (14)
C260.0394 (16)0.0554 (19)0.0463 (18)0.0166 (14)0.0118 (14)0.0158 (15)
C290.0415 (15)0.0431 (16)0.0354 (15)0.0120 (12)0.0161 (12)0.0100 (12)
C300.0554 (19)0.0478 (18)0.0404 (17)0.0164 (14)0.0184 (15)0.0143 (14)
C320.0357 (14)0.0451 (16)0.0380 (15)0.0087 (12)0.0117 (12)0.0164 (12)
C340.0389 (15)0.0416 (15)0.0342 (15)0.0108 (12)0.0106 (12)0.0102 (12)
C360.0364 (14)0.0368 (14)0.0375 (15)0.0103 (11)0.0089 (12)0.0143 (12)
C380.0415 (15)0.0428 (16)0.0332 (14)0.0121 (12)0.0123 (12)0.0130 (12)
Geometric parameters (Å, º) top
N1—C111.144 (5)C11—C301.451 (5)
N4—C321.344 (4)C13—C301.393 (5)
N4—C341.406 (4)C13—H13A0.9300
N4—C141.468 (4)C14—H14A0.9700
N6—C321.348 (4)C14—H14B0.9700
N6—C361.400 (4)C17—C221.371 (5)
N6—C291.482 (4)C17—C181.405 (6)
C2—C61.256 (7)C17—H17A0.9300
C2—C141.484 (7)C18—C261.389 (5)
C2—H2A0.9300C18—H18A0.9300
C3—C41.379 (7)C20—C381.388 (5)
C3—C201.387 (5)C20—H20A0.9300
C3—H3A0.9300C22—C341.392 (4)
C4—C131.383 (6)C22—H22A0.9300
C4—H4A0.9300C26—C361.389 (4)
C6—H6A0.9600C26—H26A0.9300
C6—H6B0.9600C29—C381.514 (4)
C8—C321.484 (4)C29—H29A0.9700
C8—H8A0.9600C29—H29B0.9700
C8—H8B0.9600C30—C381.403 (5)
C8—H8C0.9600C34—C361.391 (4)
C32—N4—C34108.8 (3)C22—C17—H17A118.8
C32—N4—C14126.9 (3)C18—C17—H17A118.8
C34—N4—C14124.3 (3)C26—C18—C17121.6 (3)
C32—N6—C36108.6 (2)C26—C18—H18A119.2
C32—N6—C29126.6 (2)C17—C18—H18A119.2
C36—N6—C29124.8 (2)C3—C20—C38121.4 (4)
C6—C2—C14128.9 (5)C3—C20—H20A119.3
C6—C2—H2A115.5C38—C20—H20A119.3
C14—C2—H2A115.5C17—C22—C34115.8 (3)
C4—C3—C20120.0 (4)C17—C22—H22A122.1
C4—C3—H3A120.0C34—C22—H22A122.1
C20—C3—H3A120.0C36—C26—C18116.0 (3)
C3—C4—C13120.3 (3)C36—C26—H26A122.0
C3—C4—H4A119.9C18—C26—H26A122.0
C13—C4—H4A119.9N6—C29—C38113.6 (2)
C2—C6—H6A118.5N6—C29—H29A108.9
C2—C6—H6B121.6C38—C29—H29A108.9
H6A—C6—H6B120.0N6—C29—H29B108.9
C32—C8—H8A109.5C38—C29—H29B108.9
C32—C8—H8B109.5H29A—C29—H29B107.7
H8A—C8—H8B109.5C13—C30—C38121.1 (3)
C32—C8—H8C109.5C13—C30—C11117.2 (3)
H8A—C8—H8C109.5C38—C30—C11121.7 (3)
H8B—C8—H8C109.5N4—C32—N6109.3 (3)
N1—C11—C30178.4 (4)N4—C32—C8124.5 (3)
C4—C13—C30119.5 (4)N6—C32—C8126.2 (3)
C4—C13—H13A120.3C36—C34—C22122.4 (3)
C30—C13—H13A120.3C36—C34—N4106.4 (3)
N4—C14—C2113.6 (3)C22—C34—N4131.2 (3)
N4—C14—H14A108.8C26—C36—C34121.7 (3)
C2—C14—H14A108.8C26—C36—N6131.3 (3)
N4—C14—H14B108.8C34—C36—N6106.9 (2)
C2—C14—H14B108.8C20—C38—C30117.8 (3)
H14A—C14—H14B107.7C20—C38—C29119.5 (3)
C22—C17—C18122.4 (3)C30—C38—C29122.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···Br10.932.913.738 (4)149
C14—H14A···Br1i0.972.823.740 (3)158
C20—H20A···Br1ii0.932.913.787 (4)158
C29—H29A···Br1iii0.972.903.798 (3)155
C29—H29B···Br1ii0.972.913.848 (3)164
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y−1, z; (iii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formulaC19H18N3+·Br−
Mr368.27
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.123 (5), 10.100 (4), 10.520 (4)
α, β, γ (°)98.924 (2), 108.490 (18), 102.851 (11)
V (Å3)869.2 (7)
Z2
Radiation typeMo Kα
µ (mm−1)2.37
Crystal size (mm)0.15 × 0.10 × 0.07
Data collection
DiffractometerRigaku Mercury2 CCD
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.872, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		9212, 4233, 3434
Rint0.035
(sin θ/λ)max (Å−1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.143, 0.92
No. of reflections4233
No. of parameters209
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.38, −0.40

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···Br10.932.913.738 (4)148.9
C14—H14A···Br1i0.972.823.740 (3)158.1
C20—H20A···Br1ii0.932.913.787 (4)157.7
C29—H29A···Br1iii0.972.903.798 (3)155.3
C29—H29B···Br1ii0.972.913.848 (3)163.5
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y−1, z; (iii) −x, −y+1, −z.
 

Acknowledgements

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

References

First citationAakeroy, C. B., Desper, J. & &Urbina, J. F. (2005). Cryst. Growth Des. 5, 1283–1293.  Google Scholar
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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o23
https://doi.org/10.1107/S1600536807060874
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