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In the crystal structure of the title compound, C18H17Br2N2+·PF6, four F atoms of the hexa­fluoro­phosphate anion are disordered. The hexa­fluoro­phosphate ions are linked to 1-benzyl-3-[4-(dibromo­meth­yl)benz­yl]imidazolium cations by C—H...F hydrogen bonds, which may be effective in the stabilization of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038852/hk2132sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038852/hk2132Isup2.hkl
Contains datablock I

CCDC reference: 624731

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.036
  • wR factor = 0.099
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 36.00 Perc. PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. F1' .. 3.02 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br2 .. F3' .. 3.21 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br2 .. F2 .. 3.32 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

1-Benzyl-3-[4-(dibromomethyl)benzyl]imidazolium hexafluorophosphate top
Crystal data top
C18H17Br2N2+·PF6F(000) = 1112
Mr = 566.13Dx = 1.865 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 15567 reflections
a = 9.9544 (2) Åθ = 3.2–27.5°
b = 14.2182 (3) ŵ = 4.16 mm1
c = 14.2552 (3) ÅT = 153 K
β = 91.963 (1)°Block, white
V = 2016.41 (7) Å30.51 × 0.47 × 0.44 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4610 independent reflections
Radiation source: Rotating Anode4042 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(Blessing, 1995)
h = 1212
Tmin = 0.138, Tmax = 0.160k = 1718
19223 measured reflectionsl = 1818
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0546P)2 + 1.96P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
4610 reflectionsΔρmax = 0.84 e Å3
282 parametersΔρmin = 0.74 e Å3
10 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0095 (7)
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*/UeqOcc. (<1)
P0.17264 (7)0.48423 (5)0.86395 (5)0.02206 (16)
Br10.29721 (3)0.33642 (2)0.59898 (2)0.03139 (12)
Br20.54390 (3)0.21306 (2)0.53314 (2)0.03532 (12)
F10.1285 (4)0.4117 (2)0.7843 (3)0.0857 (13)0.851 (4)
F20.2150 (4)0.5529 (3)0.9454 (2)0.0839 (12)0.851 (4)
F30.2401 (4)0.5502 (3)0.7909 (3)0.0763 (12)0.851 (4)
F40.1066 (3)0.4123 (3)0.9334 (3)0.0811 (12)0.851 (4)
F1'0.199 (2)0.4534 (16)0.7598 (6)0.0857 (13)0.149 (4)
F2'0.136 (2)0.5243 (17)0.9632 (8)0.0839 (12)0.149 (4)
F3'0.2501 (14)0.5801 (7)0.8503 (15)0.049 (4)0.149 (4)
F4'0.0899 (19)0.3900 (9)0.8686 (18)0.0811 (12)0.149 (4)
F50.0349 (2)0.53684 (17)0.8453 (2)0.0722 (8)
F60.30983 (18)0.42964 (17)0.8802 (2)0.0715 (8)
N10.2095 (2)0.71473 (16)0.17151 (15)0.0223 (5)
N20.3376 (2)0.59222 (15)0.17244 (15)0.0217 (4)
C10.0616 (3)0.7751 (2)0.0251 (2)0.0305 (6)
H10.02890.71260.02020.037*
C20.0672 (3)0.8178 (3)0.1120 (2)0.0383 (7)
H20.03760.78440.16660.046*
C30.1153 (3)0.9081 (2)0.1203 (2)0.0356 (7)
H30.11810.93690.18030.043*
C40.1593 (3)0.9567 (2)0.0413 (2)0.0367 (7)
H40.19391.01860.04680.044*
C50.1526 (3)0.9141 (2)0.0470 (2)0.0301 (6)
H50.18190.94760.10160.036*
C60.1037 (3)0.82372 (19)0.05510 (19)0.0233 (5)
C70.0948 (3)0.7779 (2)0.1502 (2)0.0270 (6)
H7A0.09200.82740.19890.032*
H7B0.01020.74150.15220.032*
C80.2181 (3)0.62548 (19)0.14427 (18)0.0227 (5)
H80.15030.59130.11040.027*
C90.3279 (3)0.7393 (2)0.2178 (2)0.0289 (6)
H90.34960.79900.24420.035*
C100.4068 (3)0.6627 (2)0.2183 (2)0.0288 (6)
H100.49500.65820.24560.035*
C110.3846 (3)0.49480 (19)0.15784 (19)0.0266 (6)
H11A0.47790.49620.13590.032*
H11B0.32730.46450.10840.032*
C120.3805 (3)0.43704 (18)0.24708 (18)0.0213 (5)
C130.4738 (3)0.45216 (19)0.3206 (2)0.0263 (6)
H130.53980.49990.31510.032*
C140.4717 (3)0.39860 (19)0.4016 (2)0.0260 (6)
H140.53450.41070.45180.031*
C150.3775 (3)0.32713 (18)0.40936 (18)0.0212 (5)
C160.2849 (3)0.3114 (2)0.3358 (2)0.0256 (5)
H160.22070.26230.34030.031*
C170.2858 (3)0.3671 (2)0.25587 (19)0.0262 (6)
H170.22050.35690.20670.031*
C180.3711 (3)0.2663 (2)0.49434 (19)0.0263 (5)
H180.30860.21300.47900.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P0.0238 (3)0.0224 (3)0.0200 (3)0.0029 (2)0.0014 (3)0.0005 (2)
Br10.03370 (18)0.03511 (19)0.02565 (17)0.00148 (11)0.00530 (12)0.00204 (11)
Br20.03993 (19)0.0397 (2)0.02621 (17)0.01365 (12)0.00067 (13)0.00680 (12)
F10.109 (3)0.066 (2)0.080 (2)0.001 (2)0.031 (2)0.044 (2)
F20.100 (3)0.088 (3)0.062 (2)0.008 (2)0.027 (2)0.0462 (19)
F30.081 (2)0.076 (3)0.075 (2)0.0101 (19)0.034 (2)0.053 (2)
F40.0675 (18)0.080 (2)0.098 (3)0.0100 (16)0.035 (2)0.052 (2)
F1'0.109 (3)0.066 (2)0.080 (2)0.001 (2)0.031 (2)0.044 (2)
F2'0.100 (3)0.088 (3)0.062 (2)0.008 (2)0.027 (2)0.0462 (19)
F3'0.037 (7)0.031 (7)0.079 (13)0.019 (6)0.001 (8)0.009 (8)
F4'0.0675 (18)0.080 (2)0.098 (3)0.0100 (16)0.035 (2)0.052 (2)
F50.0361 (11)0.0507 (14)0.129 (3)0.0122 (10)0.0060 (13)0.0073 (15)
F60.0292 (10)0.0512 (14)0.134 (3)0.0070 (9)0.0012 (13)0.0344 (15)
N10.0262 (11)0.0218 (11)0.0191 (10)0.0017 (8)0.0022 (9)0.0024 (8)
N20.0269 (11)0.0191 (11)0.0191 (10)0.0014 (8)0.0029 (9)0.0038 (8)
C10.0338 (15)0.0298 (15)0.0280 (14)0.0048 (11)0.0054 (12)0.0027 (11)
C20.0428 (17)0.050 (2)0.0220 (14)0.0049 (14)0.0042 (13)0.0046 (13)
C30.0334 (15)0.0480 (19)0.0257 (14)0.0007 (13)0.0063 (12)0.0107 (13)
C40.0422 (17)0.0313 (16)0.0364 (17)0.0062 (13)0.0001 (13)0.0085 (13)
C50.0343 (15)0.0272 (15)0.0284 (14)0.0002 (11)0.0035 (12)0.0003 (11)
C60.0208 (12)0.0257 (13)0.0235 (13)0.0053 (10)0.0033 (10)0.0036 (10)
C70.0300 (14)0.0266 (14)0.0249 (13)0.0072 (11)0.0079 (11)0.0026 (10)
C80.0243 (12)0.0243 (13)0.0197 (12)0.0012 (10)0.0028 (10)0.0008 (10)
C90.0396 (15)0.0223 (14)0.0243 (13)0.0043 (11)0.0070 (12)0.0009 (10)
C100.0300 (14)0.0268 (14)0.0290 (14)0.0039 (10)0.0074 (12)0.0056 (11)
C110.0337 (14)0.0233 (14)0.0230 (13)0.0060 (10)0.0046 (11)0.0011 (10)
C120.0242 (12)0.0196 (12)0.0203 (12)0.0054 (9)0.0037 (10)0.0003 (9)
C130.0253 (13)0.0233 (14)0.0303 (14)0.0028 (10)0.0003 (11)0.0032 (11)
C140.0238 (13)0.0247 (14)0.0290 (14)0.0027 (10)0.0063 (11)0.0020 (11)
C150.0231 (12)0.0184 (12)0.0220 (12)0.0022 (9)0.0006 (10)0.0007 (9)
C160.0255 (13)0.0225 (13)0.0284 (14)0.0054 (10)0.0041 (11)0.0011 (11)
C170.0282 (13)0.0260 (14)0.0241 (13)0.0007 (10)0.0047 (11)0.0015 (11)
C180.0310 (14)0.0247 (14)0.0231 (13)0.0013 (11)0.0002 (11)0.0013 (10)
Geometric parameters (Å, º) top
P—F21.564 (2)C4—H40.9500
P—F31.569 (2)C5—C61.381 (4)
P—F4'1.575 (3)C5—H50.9500
P—F51.5766 (18)C6—C71.508 (4)
P—F1'1.578 (3)C7—H7A0.9900
P—F2'1.579 (3)C7—H7B0.9900
P—F61.5809 (17)C8—H80.9500
P—F3'1.581 (3)C9—C101.343 (4)
P—F41.582 (2)C9—H90.9500
P—F11.585 (2)C10—H100.9500
Br1—C181.959 (3)C11—C121.516 (4)
Br2—C181.942 (3)C11—H11A0.9900
N1—C81.331 (4)C11—H11B0.9900
N1—C91.376 (4)C12—C171.379 (4)
N1—C71.476 (3)C12—C131.393 (4)
N2—C81.330 (3)C13—C141.383 (4)
N2—C101.369 (3)C13—H130.9500
N2—C111.479 (3)C14—C151.389 (4)
C1—C21.382 (4)C14—H140.9500
C1—C61.388 (4)C15—C161.390 (4)
C1—H10.9500C15—C181.492 (4)
C2—C31.377 (5)C16—C171.388 (4)
C2—H20.9500C16—H160.9500
C3—C41.379 (5)C17—H170.9500
C3—H30.9500C18—H181.0000
C4—C51.400 (4)
F2—P—F390.5 (2)C4—C3—H3120.1
F2—P—F4'128.9 (9)C3—C4—C5119.6 (3)
F3—P—F4'140.6 (9)C3—C4—H4120.2
F2—P—F592.28 (18)C5—C4—H4120.2
F3—P—F589.66 (17)C6—C5—C4120.3 (3)
F4'—P—F587.6 (8)C6—C5—H5119.8
F2—P—F1'145.4 (9)C4—C5—H5119.8
F3—P—F1'56.9 (8)C5—C6—C1119.5 (3)
F4'—P—F1'84.6 (12)C5—C6—C7120.6 (3)
F5—P—F1'98.2 (9)C1—C6—C7120.0 (3)
F3—P—F2'119.7 (9)N1—C7—C6112.3 (2)
F4'—P—F2'97.6 (12)N1—C7—H7A109.1
F5—P—F2'75.8 (9)C6—C7—H7A109.1
F1'—P—F2'173.4 (13)N1—C7—H7B109.1
F2—P—F689.3 (2)C6—C7—H7B109.1
F3—P—F690.21 (16)H7A—C7—H7B107.9
F4'—P—F691.5 (8)N2—C8—N1108.5 (2)
F5—P—F6178.40 (17)N2—C8—H8125.8
F1'—P—F680.4 (9)N1—C8—H8125.8
F2'—P—F6105.7 (9)C10—C9—N1106.7 (2)
F2—P—F3'55.4 (8)C10—C9—H9126.6
F4'—P—F3'174.9 (11)N1—C9—H9126.6
F5—P—F3'89.7 (6)C9—C10—N2107.9 (2)
F1'—P—F3'91.6 (11)C9—C10—H10126.1
F2'—P—F3'85.8 (11)N2—C10—H10126.1
F6—P—F3'91.1 (6)N2—C11—C12111.8 (2)
F2—P—F492.7 (2)N2—C11—H11A109.3
F3—P—F4176.4 (2)C12—C11—H11A109.3
F5—P—F491.96 (17)N2—C11—H11B109.3
F1'—P—F4119.6 (9)C12—C11—H11B109.3
F2'—P—F463.9 (9)H11A—C11—H11B107.9
F6—P—F488.08 (16)C17—C12—C13118.9 (2)
F3'—P—F4148.1 (8)C17—C12—C11120.4 (2)
F2—P—F1177.8 (2)C13—C12—C11120.7 (2)
F3—P—F191.6 (3)C14—C13—C12120.9 (2)
F4'—P—F149.0 (9)C14—C13—H13119.5
F5—P—F188.25 (18)C12—C13—H13119.5
F2'—P—F1144.1 (9)C13—C14—C15119.9 (2)
F6—P—F190.15 (18)C13—C14—H14120.0
F3'—P—F1126.7 (8)C15—C14—H14120.0
F4—P—F185.2 (2)C14—C15—C16119.3 (2)
C8—N1—C9108.7 (2)C14—C15—C18122.5 (2)
C8—N1—C7125.3 (2)C16—C15—C18118.2 (2)
C9—N1—C7126.0 (2)C17—C16—C15120.3 (2)
C8—N2—C10108.3 (2)C17—C16—H16119.8
C8—N2—C11125.1 (2)C15—C16—H16119.8
C10—N2—C11126.6 (2)C12—C17—C16120.6 (2)
C2—C1—C6119.9 (3)C12—C17—H17119.7
C2—C1—H1120.0C16—C17—H17119.7
C6—C1—H1120.0C15—C18—Br2113.26 (19)
C3—C2—C1120.7 (3)C15—C18—Br1110.52 (19)
C3—C2—H2119.6Br2—C18—Br1109.48 (13)
C1—C2—H2119.6C15—C18—H18107.8
C2—C3—C4119.9 (3)Br2—C18—H18107.8
C2—C3—H3120.1Br1—C18—H18107.8
C6—C1—C2—C30.5 (5)C11—N2—C10—C9178.7 (3)
C1—C2—C3—C40.4 (5)C8—N2—C11—C12103.9 (3)
C2—C3—C4—C51.0 (5)C10—N2—C11—C1274.6 (3)
C3—C4—C5—C60.7 (5)N2—C11—C12—C17108.5 (3)
C4—C5—C6—C10.2 (4)N2—C11—C12—C1372.9 (3)
C4—C5—C6—C7179.3 (3)C17—C12—C13—C140.4 (4)
C2—C1—C6—C50.8 (4)C11—C12—C13—C14179.0 (3)
C2—C1—C6—C7178.7 (3)C12—C13—C14—C151.5 (4)
C8—N1—C7—C684.2 (3)C13—C14—C15—C161.0 (4)
C9—N1—C7—C691.7 (3)C13—C14—C15—C18179.3 (3)
C5—C6—C7—N198.6 (3)C14—C15—C16—C170.6 (4)
C1—C6—C7—N181.9 (3)C18—C15—C16—C17179.1 (3)
C10—N2—C8—N10.4 (3)C13—C12—C17—C161.2 (4)
C11—N2—C8—N1178.4 (2)C11—C12—C17—C16177.3 (3)
C9—N1—C8—N20.6 (3)C15—C16—C17—C121.7 (4)
C7—N1—C8—N2177.1 (2)C14—C15—C18—Br250.0 (3)
C8—N1—C9—C100.5 (3)C16—C15—C18—Br2130.3 (2)
C7—N1—C9—C10177.0 (3)C14—C15—C18—Br173.2 (3)
N1—C9—C10—N20.3 (3)C16—C15—C18—Br1106.5 (2)
C8—N2—C10—C90.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···F2i0.952.523.016 (4)113
C9—H9···F3ii0.952.513.297 (5)141
C11—H11A···F6iii0.992.383.288 (4)152
C18—H18···F6iv1.002.473.273 (4)137
Symmetry codes: (i) x, y, z1; (ii) x, y+3/2, z1/2; (iii) x+1, y+1, z+1; (iv) x, y+1/2, z1/2.
 

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