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The title compound, C22H20N2+·Br·H2O, was synthesized from 1-benzyl­benzimidazole and 2-bromo­ethyl­benzene in dimethyl­formamide. The dihedral angle between the two phen­yl rings is 70.6 (1)°. These phen­yl rings make dihedral angles of 52.99 (9) and 83.03 (8)° with the benzimidazole ring system. The crystal structure is stabilized by inter­molecular C—H...Br and O—H...Br hydrogen-bond inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805021653/cv6545sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805021653/cv6545Isup2.hkl
Contains datablock I

CCDC reference: 282308

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.100
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.66 mm PLAT320_ALERT_2_C Check Hybridisation of C7 in Main Residue . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-Benzyl-3-(2-phenethyl)benzimidazolium bromide monohydrate top
Crystal data top
C22H20N2+·Br·H2OZ = 2
Mr = 410.32F(000) = 422
Triclinic, P1Dx = 1.422 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2334 (9) ÅCell parameters from 10373 reflections
b = 9.3684 (10) Åθ = 2.2–26.8°
c = 11.3028 (12) ŵ = 2.16 mm1
α = 99.895 (8)°T = 100 K
β = 90.607 (8)°Prism, colourless
γ = 95.637 (8)°0.66 × 0.47 × 0.26 mm
V = 958.14 (17) Å3
Data collection top
Stoe IPDS-II
diffractometer
4023 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus3811 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.053
Detector resolution: 6.67 pixels mm-1θmax = 26.7°, θmin = 2.2°
ω scansh = 1111
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1111
Tmin = 0.330, Tmax = 0.604l = 1314
10373 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0662P)2 + 0.4181P]
where P = (Fo2 + 2Fc2)/3
4023 reflections(Δ/σ)max = 0.001
244 parametersΔρmax = 1.45 e Å3
0 restraintsΔρmin = 1.06 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
N10.32580 (19)0.5492 (2)0.84749 (15)0.0169 (5)
N20.49570 (19)0.73024 (19)0.85838 (15)0.0162 (5)
C10.4580 (2)0.4893 (2)0.84798 (17)0.0167 (5)
C20.4898 (2)0.3469 (2)0.84448 (18)0.0197 (6)
C30.6362 (3)0.3269 (2)0.85125 (19)0.0218 (6)
C40.7453 (2)0.4444 (3)0.86176 (19)0.0214 (6)
C50.7138 (2)0.5856 (3)0.86393 (18)0.0189 (6)
C60.5664 (2)0.6057 (2)0.85612 (17)0.0161 (5)
C70.3524 (2)0.6923 (2)0.85220 (17)0.0173 (5)
C80.5652 (2)0.8795 (2)0.86259 (19)0.0186 (6)
C90.6364 (2)0.8973 (2)0.74607 (19)0.0168 (5)
C100.7840 (2)0.9455 (2)0.7454 (2)0.0220 (6)
C110.8481 (3)0.9662 (3)0.6382 (2)0.0283 (7)
C120.7675 (3)0.9368 (2)0.5321 (2)0.0271 (7)
C130.6196 (3)0.8881 (2)0.5320 (2)0.0235 (6)
C140.5544 (2)0.8696 (2)0.6392 (2)0.0200 (6)
C150.1798 (2)0.4689 (2)0.83453 (19)0.0198 (6)
C160.1471 (2)0.3936 (2)0.70472 (19)0.0212 (6)
C170.1739 (2)0.4971 (2)0.61673 (19)0.0184 (5)
C180.2836 (2)0.4774 (2)0.5335 (2)0.0213 (6)
C190.3105 (2)0.5724 (3)0.4531 (2)0.0227 (6)
C200.2297 (3)0.6889 (2)0.45547 (19)0.0218 (6)
C210.1212 (3)0.7106 (2)0.5389 (2)0.0234 (6)
C220.0927 (2)0.6148 (2)0.6185 (2)0.0215 (6)
O10.0329 (2)0.2233 (2)1.0233 (2)0.0351 (6)
Br10.19898 (2)0.03845 (2)0.84225 (2)0.0221 (1)
H20.417200.269600.838000.0240*
H30.662900.233300.848800.0260*
H40.842100.426200.867500.0260*
H50.786400.662900.870200.0230*
H8A0.637900.902000.927500.0220*
H8B0.492500.947700.879100.0220*
H100.839400.963900.816600.0260*
H110.946201.000100.638000.0340*
H120.811600.949400.460500.0330*
H130.565000.868100.460400.0280*
H140.455600.838600.639500.0240*
H15A0.107600.535800.859000.0240*
H15B0.173500.396600.886700.0240*
H16A0.207800.314400.685300.0260*
H16B0.046200.352100.696800.0260*
H180.339400.399700.532000.0260*
H190.383200.557500.397400.0270*
H200.247800.752700.401500.0260*
H210.067300.789800.541300.0280*
H220.018900.629400.673300.0260*
H1W0.019 (4)0.180 (4)0.971 (4)0.043 (10)*
H2W0.059 (5)0.164 (5)1.059 (4)0.053 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0128 (8)0.0241 (9)0.0134 (8)0.0001 (7)0.0007 (6)0.0032 (6)
N20.0142 (8)0.0206 (9)0.0135 (7)0.0005 (6)0.0009 (6)0.0027 (6)
C10.0150 (9)0.0244 (10)0.0108 (8)0.0016 (8)0.0012 (7)0.0038 (7)
C20.0220 (10)0.0220 (10)0.0149 (9)0.0010 (8)0.0025 (8)0.0035 (8)
C30.0248 (11)0.0240 (10)0.0178 (10)0.0071 (9)0.0036 (8)0.0043 (8)
C40.0164 (10)0.0321 (12)0.0170 (9)0.0067 (8)0.0031 (8)0.0051 (8)
C50.0154 (10)0.0271 (11)0.0136 (9)0.0009 (8)0.0011 (7)0.0029 (8)
C60.0158 (9)0.0219 (10)0.0105 (8)0.0021 (8)0.0020 (7)0.0023 (7)
C70.0162 (9)0.0234 (10)0.0125 (9)0.0020 (8)0.0006 (7)0.0033 (8)
C80.0174 (10)0.0185 (10)0.0188 (10)0.0007 (8)0.0006 (8)0.0016 (8)
C90.0154 (9)0.0153 (9)0.0202 (10)0.0021 (7)0.0027 (7)0.0038 (7)
C100.0152 (10)0.0200 (10)0.0301 (11)0.0014 (8)0.0002 (8)0.0026 (9)
C110.0178 (11)0.0236 (11)0.0423 (14)0.0005 (8)0.0121 (10)0.0029 (10)
C120.0330 (13)0.0203 (10)0.0294 (12)0.0050 (9)0.0167 (10)0.0057 (9)
C130.0297 (12)0.0237 (10)0.0190 (10)0.0084 (9)0.0044 (9)0.0060 (8)
C140.0152 (9)0.0243 (10)0.0207 (10)0.0029 (8)0.0015 (8)0.0043 (8)
C150.0131 (9)0.0264 (11)0.0188 (10)0.0040 (8)0.0004 (7)0.0044 (8)
C160.0185 (10)0.0241 (10)0.0200 (10)0.0012 (8)0.0030 (8)0.0028 (8)
C170.0157 (9)0.0219 (10)0.0160 (9)0.0007 (8)0.0043 (7)0.0000 (8)
C180.0205 (10)0.0234 (10)0.0195 (10)0.0059 (8)0.0012 (8)0.0006 (8)
C190.0208 (10)0.0281 (11)0.0183 (10)0.0039 (9)0.0022 (8)0.0004 (8)
C200.0242 (11)0.0236 (10)0.0171 (9)0.0013 (8)0.0026 (8)0.0034 (8)
C210.0216 (11)0.0235 (10)0.0254 (11)0.0079 (8)0.0018 (8)0.0018 (9)
C220.0172 (10)0.0266 (11)0.0200 (10)0.0055 (8)0.0014 (8)0.0003 (8)
O10.0303 (10)0.0256 (9)0.0496 (12)0.0036 (8)0.0149 (9)0.0057 (9)
Br10.0159 (1)0.0250 (1)0.0253 (1)0.0011 (1)0.0010 (1)0.0048 (1)
Geometric parameters (Å, º) top
O1—H1W0.84 (4)C18—C191.385 (3)
O1—H2W0.76 (5)C19—C201.378 (3)
N1—C11.393 (3)C20—C211.389 (4)
N1—C151.471 (3)C21—C221.386 (3)
N1—C71.331 (3)C2—H20.9300
N2—C71.334 (3)C3—H30.9300
N2—C81.473 (3)C4—H40.9300
N2—C61.389 (3)C5—H50.9300
C1—C21.388 (3)C8—H8A0.9700
C1—C61.396 (3)C8—H8B0.9700
C2—C31.386 (3)C10—H100.9300
C3—C41.406 (3)C11—H110.9300
C4—C51.378 (4)C12—H120.9300
C5—C61.396 (3)C13—H130.9300
C8—C91.506 (3)C14—H140.9300
C9—C101.394 (3)C15—H15B0.9700
C9—C141.391 (3)C15—H15A0.9700
C10—C111.389 (3)C16—H16B0.9700
C11—C121.377 (3)C16—H16A0.9700
C12—C131.397 (4)C18—H180.9300
C13—C141.388 (3)C19—H190.9300
C15—C161.528 (3)C20—H200.9300
C16—C171.510 (3)C21—H210.9300
C17—C181.394 (3)C22—H220.9300
C17—C221.391 (3)
Br1···C23.7431 (19)C5···H15Biv2.9700
Br1···C7i3.6824 (19)C6···H19vi3.0700
Br1···O13.373 (2)C7···H143.0800
Br1···O1ii3.356 (2)C8···H53.0300
Br1···H1W2.54 (4)C10···H3vii3.0700
Br1···H11iii3.2200C11···H20viii2.9600
Br1···H22.8200C11···H21x2.8500
Br1···H8Bi2.9700C12···H20viii2.8900
Br1···H2Wii2.61 (5)C12···H21viii3.0900
Br1···H8Aiv2.9300C13···H13viii2.9700
O1···C5iv3.408 (3)C13···H18vi2.7300
O1···C7v3.387 (3)C15···H223.0200
O1···Br13.373 (2)C15···H23.0200
O1···Br1ii3.356 (2)C20···H16Bix3.0100
O1···H5iv2.6100C20···H143.0000
O1···H15Av2.5800C21···H16Bix3.0000
N1···C4iv3.350 (3)C22···H15A2.9400
N1···N22.180 (3)H1W···Br12.54 (4)
N1···C3iv3.406 (3)H2···C153.0200
N2···N12.180 (3)H2···Br12.8200
N2···H142.8600H2W···Br1ii2.61 (5)
C1···C1iv3.483 (3)H3···C10i3.0700
C1···C2iv3.558 (3)H4···H15Ax2.5700
C2···C6iv3.389 (3)H5···C83.0300
C2···Br13.7431 (19)H5···O1iv2.6100
C2···C1iv3.558 (3)H8A···Br1iv2.9300
C3···N1iv3.406 (3)H8A···C53.0800
C3···C7iv3.389 (3)H8A···H102.3400
C4···N1iv3.350 (3)H8B···Br1vii2.9700
C4···C15iv3.436 (3)H10···H8A2.3400
C4···C19vi3.565 (3)H11···Br1xi3.2200
C5···C93.541 (3)H11···H12xii2.5500
C5···O1iv3.408 (3)H11···H21x2.4600
C6···C2iv3.389 (3)H12···H21viii2.5900
C7···Br1vii3.6824 (19)H12···H11xii2.5500
C7···O1v3.387 (3)H13···C13viii2.9700
C7···C173.284 (3)H14···C203.0000
C7···C143.591 (3)H14···N22.8600
C7···C3iv3.389 (3)H14···C73.0800
C7···C223.481 (3)H15A···H222.5700
C9···C53.541 (3)H15A···O1v2.5800
C12···C20viii3.483 (3)H15A···C222.9400
C12···C21viii3.588 (3)H15A···H4xiii2.5700
C13···C18vi3.580 (3)H15B···C5iv2.9700
C13···C13viii3.346 (3)H15B···C23.0300
C14···C73.591 (3)H15B···C4iv3.0200
C15···C4iv3.436 (3)H16A···H182.3300
C17···C22ix3.553 (3)H16A···C13.0900
C17···C21ix3.462 (3)H16B···C20ix3.0100
C17···C73.284 (3)H16B···C21ix3.0000
C18···C13vi3.580 (3)H18···C13vi2.7300
C19···C4vi3.565 (3)H18···H16A2.3300
C20···C12viii3.483 (3)H19···C6vi3.0700
C21···C12viii3.588 (3)H20···C3vi3.0600
C21···C17ix3.462 (3)H20···C11viii2.9600
C22···C17ix3.553 (3)H20···C12viii2.8900
C22···C22ix3.454 (3)H21···C12viii3.0900
C22···C73.481 (3)H21···C11xiii2.8500
C1···H16A3.0900H21···H11xiii2.4600
C2···H15B3.0300H21···H12viii2.5900
C3···H20vi3.0600H22···C153.0200
C4···H15Biv3.0200H22···H15A2.5700
C5···H8A3.0800
H1W—O1—H2W103 (4)C2—C3—H3119.00
C1—N1—C7108.76 (17)C3—C4—H4119.00
C7—N1—C15124.55 (17)C5—C4—H4119.00
C1—N1—C15126.54 (17)C6—C5—H5122.00
C6—N2—C8126.43 (16)C4—C5—H5122.00
C7—N2—C8124.91 (17)N2—C8—H8A109.00
C6—N2—C7108.63 (17)C9—C8—H8A109.00
N1—C1—C6106.16 (17)C9—C8—H8B109.00
C2—C1—C6122.33 (17)N2—C8—H8B109.00
N1—C1—C2131.49 (18)H8A—C8—H8B108.00
C1—C2—C3115.99 (17)C11—C10—H10120.00
C2—C3—C4121.71 (19)C9—C10—H10120.00
C3—C4—C5122.30 (19)C12—C11—H11120.00
C4—C5—C6116.0 (2)C10—C11—H11120.00
N2—C6—C5131.7 (2)C11—C12—H12120.00
C1—C6—C5121.63 (19)C13—C12—H12120.00
N2—C6—C1106.60 (16)C12—C13—H13120.00
N1—C7—N2109.83 (17)C14—C13—H13120.00
N2—C8—C9111.57 (16)C13—C14—H14120.00
C8—C9—C14120.18 (17)C9—C14—H14120.00
C10—C9—C14119.72 (19)N1—C15—H15A109.00
C8—C9—C10120.07 (18)N1—C15—H15B109.00
C9—C10—C11119.8 (2)C16—C15—H15B109.00
C10—C11—C12120.5 (2)H15A—C15—H15B108.00
C11—C12—C13120.0 (2)C16—C15—H15A109.00
C12—C13—C14119.8 (2)C15—C16—H16B109.00
C9—C14—C13120.19 (19)C17—C16—H16A109.00
N1—C15—C16111.07 (16)C17—C16—H16B109.00
C15—C16—C17112.18 (16)H16A—C16—H16B108.00
C16—C17—C18120.05 (17)C15—C16—H16A109.00
C16—C17—C22121.13 (18)C19—C18—H18120.00
C18—C17—C22118.81 (18)C17—C18—H18120.00
C17—C18—C19120.69 (18)C18—C19—H19120.00
C18—C19—C20120.17 (19)C20—C19—H19120.00
C19—C20—C21119.66 (19)C21—C20—H20120.00
C20—C21—C22120.4 (2)C19—C20—H20120.00
C17—C22—C21120.3 (2)C20—C21—H21120.00
C1—C2—H2122.00C22—C21—H21120.00
C3—C2—H2122.00C17—C22—H22120.00
C4—C3—H3119.00C21—C22—H22120.00
C7—N1—C1—C2179.9 (2)C3—C4—C5—C60.6 (3)
C15—N1—C1—C24.5 (3)C4—C5—C6—N2178.3 (2)
C7—N1—C1—C61.4 (2)C4—C5—C6—C10.7 (3)
C15—N1—C1—C6176.97 (18)N2—C8—C9—C10123.40 (19)
C1—N1—C15—C1674.7 (2)N2—C8—C9—C1458.4 (2)
C7—N1—C15—C16100.3 (2)C14—C9—C10—C110.3 (3)
C15—N1—C7—N2177.05 (17)C8—C9—C14—C13179.04 (18)
C1—N1—C7—N21.3 (2)C10—C9—C14—C130.8 (3)
C8—N2—C7—N1178.83 (17)C8—C9—C10—C11177.9 (2)
C6—N2—C8—C970.0 (2)C9—C10—C11—C121.2 (4)
C7—N2—C6—C5177.8 (2)C10—C11—C12—C131.1 (4)
C8—N2—C6—C54.2 (3)C11—C12—C13—C140.0 (3)
C7—N2—C8—C9107.7 (2)C12—C13—C14—C91.0 (3)
C6—N2—C7—N10.8 (2)N1—C15—C16—C1751.7 (2)
C7—N2—C6—C10.1 (2)C15—C16—C17—C18114.9 (2)
C8—N2—C6—C1177.93 (18)C15—C16—C17—C2263.7 (2)
N1—C1—C6—N20.9 (2)C16—C17—C22—C21178.46 (19)
N1—C1—C2—C3177.5 (2)C18—C17—C22—C210.2 (3)
C6—C1—C2—C30.9 (3)C22—C17—C18—C190.6 (3)
C2—C1—C6—N2179.57 (18)C16—C17—C18—C19179.29 (19)
N1—C1—C6—C5177.25 (18)C17—C18—C19—C200.7 (3)
C2—C1—C6—C51.5 (3)C18—C19—C20—C210.0 (3)
C1—C2—C3—C40.4 (3)C19—C20—C21—C220.8 (4)
C2—C3—C4—C51.1 (3)C20—C21—C22—C170.9 (3)
Symmetry codes: (i) x, y1, z; (ii) x, y, z+2; (iii) x1, y1, z; (iv) x+1, y+1, z+2; (v) x, y+1, z+2; (vi) x+1, y+1, z+1; (vii) x, y+1, z; (viii) x+1, y+2, z+1; (ix) x, y+1, z+1; (x) x+1, y, z; (xi) x+1, y+1, z; (xii) x+2, y+2, z+1; (xiii) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1W···Br10.84 (4)2.54 (4)3.373 (2)170 (4)
O1—H2W···Br1ii0.76 (5)2.61 (5)3.356 (2)168 (5)
C2—H2···Br10.932.823.7431 (19)175
C15—H15A···O1v0.972.583.458 (3)151
Symmetry codes: (ii) x, y, z+2; (v) x, y+1, z+2.
 

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