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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2668.
Published online 2010 September 30. doi:  10.1107/S1600536810038006
PMCID: PMC2983333

1,1′,2,2′-Tetra­methyl-3,3′-(p-phenyl­ene­dimethyl­ene)diimidazol-1-ium bis­[bis­(trifluoro­methyl­sulfon­yl)imide]

Abstract

The cation of the imidazolium-based ionic-liquid title salt, C16H24N4 2+·2C2F6NO4S2 , lies on a center of inversion; in the cation, the five-membered imidazolium ring is aligned at 84.4 (1)° with respect to the phenyl­ene ring; the angle at the methyl­ene C atom is 113.0 (2)°. In the anion, the negative charge formally resides on the two-coordinate N atom; the S—N—S angle at this atom is 125.2 (1)°.

Related literature

For the tetra­fluoro­borate and hexa­fluoro­phosphate salts, see: Puvaneswary et al. (2009a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2668-scheme1.jpg

Experimental

Crystal data

  • C16H24N4 2+·2C2F6NO4S2
  • M r = 856.71
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2668-efi1.jpg
  • a = 8.7195 (7) Å
  • b = 13.710 (1) Å
  • c = 13.8351 (11) Å
  • β = 92.290 (1)°
  • V = 1652.6 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.41 mm−1
  • T = 100 K
  • 0.40 × 0.30 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.853, T max = 0.922
  • 10192 measured reflections
  • 3744 independent reflections
  • 3191 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.092
  • S = 1.02
  • 3744 reflections
  • 237 parameters
  • H-atom parameters constrained
  • Δρmax = 0.48 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038006/jh2208sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038006/jh2208Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (grant No. TA010/2010 A) for supporting this study.

supplementary crystallographic information

Comment

We have previously reported 1,1',2,2'-tetramethyl-3,3'-(p-phenylenedimethylene)-bis(imidazol-1-ium) salts (Puvaneswary et al., 2009a, 2009b). Such compounds are ionic-liquid salts based on an imidazolium entity. The principal feauture of these salts is the non-nucleophilic nature of the counterion. The present bis(trifluoromethanesulfonyl)imide salt (Scheme I, Fig. 1) represents another example of such an anion. The cation lies on a center-of-inversion. The five-membered limidazolyl ring is aligned at with respect to the phenylene ring 84.4 (1) °; the angle at the methylene carbon is 113.0 (2) °. In the anion, the negative charge formally resides on the two-coordinate nitrogen; the angle at this atom is 125.2 (1) °.

Experimental

1,1',2,2'-Tetramethyl-3,3'-(p-phenylenedimethylene)-bis(imidazol-1-ium) bromide (1 mmol) and lithium bis(trifluoromethanesulfonyl)imide (2 mmol) were mixed in water for 2 h to give a solid material. This was collected and recrystallized from ethyl acetate

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C16H24N42+ 2C2F6NO4S2- at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry-related atoms are not labeled.

Crystal data

C16H24N42+·2C2F6NO4S2F(000) = 868
Mr = 856.71Dx = 1.722 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4645 reflections
a = 8.7195 (7) Åθ = 2.7–28.4°
b = 13.710 (1) ŵ = 0.41 mm1
c = 13.8351 (11) ÅT = 100 K
β = 92.290 (1)°Block, colorless
V = 1652.6 (2) Å30.40 × 0.30 × 0.20 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer3744 independent reflections
Radiation source: fine-focus sealed tube3191 reflections with I > 2σ(I)
graphiteRint = 0.023
ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.853, Tmax = 0.922k = −14→17
10192 measured reflectionsl = −15→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.042P)2 + 1.3932P] where P = (Fo2 + 2Fc2)/3
3744 reflections(Δ/σ)max = 0.001
237 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = −0.40 e Å3

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

xyzUiso*/Ueq
S10.67739 (5)0.67845 (3)0.91285 (3)0.01904 (12)
S20.38200 (5)0.75917 (3)0.90601 (3)0.01821 (12)
F10.71875 (14)0.85090 (8)0.83605 (9)0.0308 (3)
F20.76447 (14)0.73079 (9)0.74157 (8)0.0300 (3)
F30.92506 (13)0.76619 (10)0.85879 (10)0.0390 (3)
F40.21558 (15)0.60557 (10)0.94569 (9)0.0361 (3)
F50.15962 (13)0.73471 (9)1.02456 (9)0.0308 (3)
F60.36490 (15)0.65461 (10)1.06344 (8)0.0347 (3)
O10.73759 (16)0.58470 (11)0.89041 (11)0.0289 (3)
O20.70581 (15)0.71643 (11)1.00822 (10)0.0272 (3)
O30.27597 (15)0.77674 (11)0.82658 (10)0.0277 (3)
O40.43736 (15)0.83923 (10)0.96315 (10)0.0267 (3)
N10.09231 (18)0.48286 (12)0.77903 (11)0.0211 (3)
N20.23507 (18)0.57396 (12)0.69354 (11)0.0208 (3)
N30.50715 (17)0.68460 (12)0.87134 (11)0.0196 (3)
C10.4064 (2)0.45239 (15)0.43276 (13)0.0215 (4)
H10.34170.41970.38630.026*
C20.3415 (2)0.50636 (15)0.50513 (13)0.0219 (4)
H20.23310.51030.50840.026*
C30.4355 (2)0.55475 (13)0.57304 (12)0.0170 (4)
C40.3691 (2)0.61775 (14)0.65040 (13)0.0210 (4)
H4A0.44900.62970.70190.025*
H4B0.33940.68160.62190.025*
C50.0846 (2)0.60245 (16)0.67350 (14)0.0261 (4)
H50.05100.65270.63040.031*
C6−0.0041 (2)0.54552 (15)0.72652 (14)0.0254 (4)
H6−0.11280.54760.72790.030*
C70.0391 (2)0.41044 (15)0.84840 (14)0.0242 (4)
H7A0.10060.41570.90900.036*
H7B0.05030.34480.82150.036*
H7C−0.06900.42250.86100.036*
C80.2373 (2)0.50107 (14)0.75707 (12)0.0189 (4)
C90.3763 (2)0.45077 (15)0.79565 (14)0.0239 (4)
H9A0.45120.49920.81980.036*
H9B0.42100.41230.74410.036*
H9C0.34910.40750.84870.036*
C100.7775 (2)0.76175 (15)0.83281 (14)0.0234 (4)
C110.2749 (2)0.68402 (15)0.98983 (13)0.0221 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0194 (2)0.0187 (2)0.0188 (2)0.00166 (17)−0.00064 (16)0.00181 (17)
S20.0183 (2)0.0185 (2)0.0177 (2)0.00097 (16)−0.00023 (16)0.00068 (17)
F10.0373 (7)0.0179 (6)0.0371 (7)−0.0019 (5)0.0017 (5)0.0018 (5)
F20.0377 (6)0.0311 (7)0.0217 (6)0.0021 (5)0.0066 (5)0.0019 (5)
F30.0198 (6)0.0477 (9)0.0490 (8)−0.0072 (5)−0.0028 (5)0.0098 (7)
F40.0461 (7)0.0298 (7)0.0333 (7)−0.0163 (6)0.0131 (6)−0.0077 (5)
F50.0296 (6)0.0330 (7)0.0306 (6)0.0035 (5)0.0110 (5)−0.0009 (5)
F60.0389 (7)0.0432 (8)0.0219 (6)0.0053 (6)0.0003 (5)0.0123 (5)
O10.0295 (7)0.0210 (8)0.0368 (8)0.0062 (6)0.0062 (6)0.0035 (6)
O20.0270 (7)0.0349 (9)0.0192 (7)0.0015 (6)−0.0063 (5)0.0005 (6)
O30.0225 (7)0.0388 (9)0.0217 (7)0.0031 (6)−0.0024 (5)0.0091 (6)
O40.0260 (7)0.0191 (7)0.0349 (8)−0.0001 (5)0.0008 (6)−0.0069 (6)
N10.0235 (7)0.0208 (9)0.0191 (7)0.0020 (6)0.0017 (6)−0.0006 (6)
N20.0248 (8)0.0203 (9)0.0173 (7)0.0009 (6)0.0026 (6)0.0001 (6)
N30.0191 (7)0.0207 (9)0.0189 (7)−0.0003 (6)−0.0011 (6)−0.0047 (6)
C10.0241 (9)0.0226 (10)0.0177 (8)−0.0064 (7)−0.0024 (7)−0.0027 (7)
C20.0194 (8)0.0249 (10)0.0214 (9)−0.0030 (7)0.0007 (7)−0.0015 (8)
C30.0232 (8)0.0146 (9)0.0133 (8)−0.0031 (7)0.0015 (6)0.0026 (6)
C40.0275 (9)0.0180 (10)0.0177 (8)−0.0016 (7)0.0038 (7)0.0004 (7)
C50.0282 (10)0.0263 (11)0.0237 (9)0.0080 (8)−0.0012 (8)0.0038 (8)
C60.0219 (9)0.0259 (11)0.0281 (10)0.0074 (8)−0.0027 (7)−0.0009 (8)
C70.0272 (9)0.0231 (11)0.0225 (9)−0.0008 (8)0.0046 (7)0.0051 (8)
C80.0258 (9)0.0172 (9)0.0138 (8)0.0013 (7)0.0009 (6)−0.0014 (7)
C90.0218 (9)0.0235 (10)0.0260 (10)0.0039 (7)−0.0035 (7)−0.0013 (8)
C100.0210 (9)0.0241 (11)0.0251 (9)−0.0002 (7)0.0001 (7)0.0030 (8)
C110.0249 (9)0.0234 (10)0.0182 (9)−0.0004 (7)0.0020 (7)−0.0006 (7)

Geometric parameters (Å, °)

S1—O11.4273 (15)C1—C21.384 (3)
S1—O21.4308 (14)C1—C3i1.387 (2)
S1—N31.5724 (15)C1—H10.9500
S1—C101.836 (2)C2—C31.390 (3)
S2—O41.4255 (14)C2—H20.9500
S2—O31.4280 (14)C3—C1i1.387 (2)
S2—N31.5837 (16)C3—C41.509 (2)
S2—C111.835 (2)C4—H4A0.9900
F1—C101.327 (2)C4—H4B0.9900
F2—C101.332 (2)C5—C61.338 (3)
F3—C101.323 (2)C5—H50.9500
F4—C111.331 (2)C6—H60.9500
F5—C111.327 (2)C7—H7A0.9800
F6—C111.324 (2)C7—H7B0.9800
N1—C81.335 (2)C7—H7C0.9800
N1—C61.387 (2)C8—C91.476 (3)
N1—C71.469 (2)C9—H9A0.9800
N2—C81.330 (2)C9—H9B0.9800
N2—C51.386 (2)C9—H9C0.9800
N2—C41.462 (2)
O1—S1—O2118.48 (9)C6—C5—N2106.80 (17)
O1—S1—N3108.59 (9)C6—C5—H5126.6
O2—S1—N3116.33 (8)N2—C5—H5126.6
O1—S1—C10103.95 (9)C5—C6—N1107.28 (17)
O2—S1—C10105.12 (9)C5—C6—H6126.4
N3—S1—C10102.19 (9)N1—C6—H6126.4
O4—S2—O3119.43 (9)N1—C7—H7A109.5
O4—S2—N3116.29 (8)N1—C7—H7B109.5
O3—S2—N3107.98 (8)H7A—C7—H7B109.5
O4—S2—C11104.56 (9)N1—C7—H7C109.5
O3—S2—C11104.53 (9)H7A—C7—H7C109.5
N3—S2—C11101.73 (9)H7B—C7—H7C109.5
C8—N1—C6108.92 (16)N2—C8—N1107.58 (16)
C8—N1—C7126.98 (16)N2—C8—C9125.43 (17)
C6—N1—C7124.10 (16)N1—C8—C9126.99 (17)
C8—N2—C5109.41 (16)C8—C9—H9A109.5
C8—N2—C4125.98 (16)C8—C9—H9B109.5
C5—N2—C4124.60 (16)H9A—C9—H9B109.5
S1—N3—S2125.16 (10)C8—C9—H9C109.5
C2—C1—C3i121.01 (17)H9A—C9—H9C109.5
C2—C1—H1119.5H9B—C9—H9C109.5
C3i—C1—H1119.5F3—C10—F1108.73 (17)
C1—C2—C3119.81 (17)F3—C10—F2108.50 (16)
C1—C2—H2120.1F1—C10—F2107.88 (16)
C3—C2—H2120.1F3—C10—S1110.21 (13)
C1i—C3—C2119.18 (17)F1—C10—S1111.04 (13)
C1i—C3—C4119.47 (16)F2—C10—S1110.41 (14)
C2—C3—C4121.31 (16)F6—C11—F5108.38 (15)
N2—C4—C3112.97 (15)F6—C11—F4108.32 (17)
N2—C4—H4A109.0F5—C11—F4107.65 (15)
C3—C4—H4A109.0F6—C11—S2110.87 (13)
N2—C4—H4B109.0F5—C11—S2110.29 (13)
C3—C4—H4B109.0F4—C11—S2111.22 (12)
H4A—C4—H4B107.8
O1—S1—N3—S2159.88 (11)C6—N1—C8—N20.8 (2)
O2—S1—N3—S223.18 (16)C7—N1—C8—N2−178.01 (17)
C10—S1—N3—S2−90.68 (13)C6—N1—C8—C9−179.42 (18)
O4—S2—N3—S114.34 (16)C7—N1—C8—C91.7 (3)
O3—S2—N3—S1151.77 (12)O1—S1—C10—F3−67.76 (16)
C11—S2—N3—S1−98.55 (13)O2—S1—C10—F357.41 (16)
C3i—C1—C2—C30.3 (3)N3—S1—C10—F3179.31 (14)
C1—C2—C3—C1i−0.3 (3)O1—S1—C10—F1171.70 (13)
C1—C2—C3—C4177.36 (17)O2—S1—C10—F1−63.13 (15)
C8—N2—C4—C375.5 (2)N3—S1—C10—F158.76 (15)
C5—N2—C4—C3−104.1 (2)O1—S1—C10—F252.09 (15)
C1i—C3—C4—N2−140.06 (17)O2—S1—C10—F2177.26 (13)
C2—C3—C4—N242.3 (2)N3—S1—C10—F2−60.84 (15)
C8—N2—C5—C60.2 (2)O4—S2—C11—F6−59.50 (15)
C4—N2—C5—C6179.92 (17)O3—S2—C11—F6174.21 (13)
N2—C5—C6—N10.3 (2)N3—S2—C11—F661.92 (15)
C8—N1—C6—C5−0.7 (2)O4—S2—C11—F560.54 (15)
C7—N1—C6—C5178.19 (18)O3—S2—C11—F5−65.75 (15)
C5—N2—C8—N1−0.7 (2)N3—S2—C11—F5−178.04 (13)
C4—N2—C8—N1179.66 (16)O4—S2—C11—F4179.90 (13)
C5—N2—C8—C9179.58 (18)O3—S2—C11—F453.62 (16)
C4—N2—C8—C9−0.1 (3)N3—S2—C11—F4−58.68 (15)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2208).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Puvaneswary, S., Alias, Y. & Ng, S. W. (2009a). Acta Cryst. E65, o1829. [PMC free article] [PubMed]
  • Puvaneswary, S., Alias, Y. & Ng, S. W. (2009b). Acta Cryst. E65, o1830. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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