Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o1076
doi:10.1107/S1600536812010847

2-Tri­fluoro­methyl-1H-benzimidazol-3-ium tetra­fluoro­borate–2-tri­fluoro­methyl-1H-benzimidazole–water (1/1/1)

Ming-Liang Liua*

aOrdered Matter Science Research Center, Southeast University, Nanjing 211189, People's Republic of China
*Correspondence e-mail: jgsdxlml@163.com

(Received 9 March 2012; accepted 12 March 2012; online 17 March 2012)

The asymmetric unit of the title compound, C8H6F3N2+·BF4−·C8H5F3N2·H2O, consists of two 2-trifluoro­methyl­benzimidazole mol­ecules, each of which is protonated on a 50% basis, one tetra­fluoro­borate anion and a water mol­ecule. The two 2-trifluoromethylbenzimidazole mol­ecules thus exist as half-neutral half-cation entities. They are linked by N—H⋯N hydrogen bonds involving the half-occupancy hydrogens in each mol­ecule. The F atoms of one of the trifluoro­methyl groups are disordered over two sets of sites [in a 0.518 (14):0.482 (14) ratio], as are the F atoms of the tetra­fluoroborate anion [0.507 (14):0.493 (14) ratio]. The water mol­ecule is linked to one of the 2-trifluoro­methyl­benzimidazole mol­ecules via an N—H⋯O hydrogen bond.

Related literature

The title compound was synthesized as part of our search for ferroelectric complexes. For background to ferroelectric complexes, see: Fu et al. (2011[Fu, D. W., Zhang, W., Cai, H. L., Zhang, Y., Ge, J. Z., Xiong, R. G. & Huang, S. P. (2011). J. Am. Chem. Soc. 133, 12780-12786.]); Zhang et al. (2010[Zhang, W., Chen, L. Z., Gou, M., Li, Y. H., Fu, D. W. & Xiong, R. G. (2010). Cryst. Growth Des. 10, 1025-1027.]). For related structures, see: Liu (2011a[Liu, M.-L. (2011a). Acta Cryst. E67, o2821.],b[Liu, M.-L. (2011b). Acta Cryst. E67, o3473.], 2012[Liu, M.-L. (2012). Acta Cryst. E68, o342.]).

[Scheme 1]

Experimental

Crystal data

  • C8H6F3N2+·BF4−·C8H5F3N2·H2O

  • Mr = 478.11

  • Triclinic, [P \overline 1]

  • a = 8.7897 (18) Å

  • b = 10.947 (2) Å

  • c = 11.458 (2) Å

  • α = 92.48 (3)°

  • β = 96.59 (3)°

  • γ = 113.34 (3)°

  • V = 1000.8 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.17 mm−1

  • T = 293 K

  • 0.36 × 0.32 × 0.28 mm
Data collection

  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.566, Tmax = 0.640

  • 10445 measured reflections

  • 4581 independent reflections

  • 2280 reflections with I > 2σ(I)

  • Rint = 0.039
Refinement

  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 0.195

  • S = 1.03

  • 4581 reflections

  • 355 parameters

  • 65 restraints

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N4—H4A⋯O1W 0.86 1.84 2.698 (3) 177
N1—H1⋯N3 0.86 1.86 2.718 (3) 175
N3—H3⋯N1 0.86 1.86 2.718 (3) 175

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812010847/go2047sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010847/go2047Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812010847/go2047Isup3.cml

checkCIF report


Comment top

Recently much attention has been devoted to crystals containing organic ions and inorganic ions due to the possibility of tuning their special structural features and their potential ferroelectrics properties (Fu et al., 2011; Zhang et al., 2010.). In our laboratory, the title compound has been synthesized to investigate to its potentialferroelectric properties. However, it was found that the dielectric constant of the compound as a function of temperature indicates that the permittivity is basically temperature-independent (ε = C/(T–T0)), suggesting that this compound is not ferroelectric or there may be no distinct phase transition occurring within the measured temperature (below the melting point).

The title compound, Figure 1, has an asymmetric unit which consists of two 2-trifluoromethylbenzimidazole molecules each of which is protonated on a 50% basis, one tetrafluoroborate anion,and a water molecule. The two trifluoromethylbenzimidazole moieties thus exist as a half neutral half cation entities. The two 2-trifluoromethylbenzimidazole molecules are hydrogen bonded together, on a 50/50 basis, by either the N1–H1···N3 or N3—H3···N1 hydrogen bonds, Table 1. One of the trifluoromethyl groups is disordered as is the tetraflouroborate anion. The water molecule is hydrogen bonded to one of the 2-trifluoromethylbenzimidazole molecules via the N4–H4A···O1W hydrogen bond Table 1. There are short N—H and O—H contacts to the F atoms of the anion but no analysis is made here because of the disorder in the anion.

Related literature top

The title compound was synthesized as part of our search for ferroelectric complexes. For background to ferroelectric complexes, see: Fu et al. (2011); Zhang et al. (2010). For related structures, see: Liu (2011a,b, 2012).

Experimental top

0.144 g (1 mmol) of 2-trifluoromethyl-1H-benzimidazol was firstly dissolved in 30 ml of ethanol, to which 0.088 g (1 mmol) of fluoroboric acid was added to give a solution at the ambient temperature. Single crystals suitable for X-ray structure analysis were obtained after six days by the slow evaporation of the above solution in air.

Refinement top

H atoms were treated as riding atoms with N—H, 0.86Å, C—H(aromatic), 0.95 Å, with Uiso = 1.2Ueq(C) allowed to ride. The H atoms attached to the water molecule were refined as riding atoms at positions deteremined from a difference Fourier with Uiso = 1.5Ueq(O). An examination of a difference Fourier along the line of the N1 to N3 vector showed an elongated density peak. This was found to be best modelled as two half-hydrogen atoms attached to N1 and N3. All H atom positions were checked on a final difference Fourier.

The disordered trifluoromethyl group was modelled over two sites with restrained bonds and angles based on the average values found for the non-disordered trifluoromethyl group in the other molecule. The site occupancies were refined and restraints were applied to the thermal parameters. The terafluoroborate anion is also modelled as being disordered over two sites. The site occupancies were refined and restraints were applied to the bonds, angles and the thermal parameters.

Structure description top

Recently much attention has been devoted to crystals containing organic ions and inorganic ions due to the possibility of tuning their special structural features and their potential ferroelectrics properties (Fu et al., 2011; Zhang et al., 2010.). In our laboratory, the title compound has been synthesized to investigate to its potentialferroelectric properties. However, it was found that the dielectric constant of the compound as a function of temperature indicates that the permittivity is basically temperature-independent (ε = C/(T–T0)), suggesting that this compound is not ferroelectric or there may be no distinct phase transition occurring within the measured temperature (below the melting point).

The title compound, Figure 1, has an asymmetric unit which consists of two 2-trifluoromethylbenzimidazole molecules each of which is protonated on a 50% basis, one tetrafluoroborate anion,and a water molecule. The two trifluoromethylbenzimidazole moieties thus exist as a half neutral half cation entities. The two 2-trifluoromethylbenzimidazole molecules are hydrogen bonded together, on a 50/50 basis, by either the N1–H1···N3 or N3—H3···N1 hydrogen bonds, Table 1. One of the trifluoromethyl groups is disordered as is the tetraflouroborate anion. The water molecule is hydrogen bonded to one of the 2-trifluoromethylbenzimidazole molecules via the N4–H4A···O1W hydrogen bond Table 1. There are short N—H and O—H contacts to the F atoms of the anion but no analysis is made here because of the disorder in the anion.

The title compound was synthesized as part of our search for ferroelectric complexes. For background to ferroelectric complexes, see: Fu et al. (2011); Zhang et al. (2010). For related structures, see: Liu (2011a,b, 2012).

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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme with 30% probability displacement ellipsoids. Both half hydrogens attached to N1 and N3 are included.
2-Trifluoromethyl-1H-benzimidazol-3-ium tetrafluoroborate– 2-trifluoromethyl-1H-benzimidazole–water (1/1/1) top
Crystal data top
C8H6F3N2+·BF4−·C8H5F3N2·H2OV = 1000.8 (3) Å3
Mr = 478.11Z = 2
Triclinic, P1F(000) = 480
Hall symbol: -P 1Dx = 1.587 Mg m−3
a = 8.7897 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.947 (2) Åθ = 0–25°
c = 11.458 (2) ŵ = 0.17 mm−1
α = 92.48 (3)°T = 293 K
β = 96.59 (3)°Block, colourless
γ = 113.34 (3)°0.36 × 0.32 × 0.28 mm
Data collection top
Rigaku SCXmini
diffractometer		4581 independent reflections
Radiation source: fine-focus sealed tube2280 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
CCD_Profile_fitting scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		h = −11→11
Tmin = 0.566, Tmax = 0.640k = −14→14
10445 measured reflectionsl = −14→14
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)] = 0.066H-atom parameters constrained
wR(F2) = 0.195 w = 1/[σ2(Fo2) + (0.073P)2 + 0.2894P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4581 reflectionsΔρmax = 0.30 e Å−3
355 parametersΔρmin = −0.21 e Å−3
65 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.020 (4)
Crystal data top
C8H6F3N2+·BF4−·C8H5F3N2·H2Oγ = 113.34 (3)°
Mr = 478.11V = 1000.8 (3) Å3
Triclinic, P1Z = 2
a = 8.7897 (18) ÅMo Kα radiation
b = 10.947 (2) ŵ = 0.17 mm−1
c = 11.458 (2) ÅT = 293 K
α = 92.48 (3)°0.36 × 0.32 × 0.28 mm
β = 96.59 (3)°
Data collection top
Rigaku SCXmini
diffractometer		4581 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		2280 reflections with I > 2σ(I)
Tmin = 0.566, Tmax = 0.640Rint = 0.039
10445 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06665 restraints
wR(F2) = 0.195H-atom parameters constrained
S = 1.03Δρmax = 0.30 e Å−3
4581 reflectionsΔρmin = −0.21 e Å−3
355 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
F5−0.1135 (3)0.6112 (3)0.9237 (2)0.1358 (10)
F60.0425 (3)0.6539 (3)1.0868 (3)0.1405 (11)
F7−0.1136 (3)0.7537 (3)1.0522 (3)0.1382 (10)
N10.1904 (3)0.7918 (2)0.8667 (2)0.0594 (6)
H10.16760.71650.82740.071*0.50
N20.1829 (3)0.9413 (3)0.9962 (2)0.0671 (7)
H2A0.15310.97531.05390.081*
C1−0.0170 (5)0.7072 (4)1.0035 (3)0.0815 (10)
C20.1171 (4)0.8130 (3)0.9543 (2)0.0593 (7)
C30.3121 (3)0.9151 (3)0.8501 (2)0.0562 (7)
C40.4274 (4)0.9514 (3)0.7713 (3)0.0740 (9)
H40.43380.88850.71710.089*
C50.5317 (5)1.0842 (4)0.7770 (3)0.0882 (11)
H50.61021.11190.72510.106*
C60.5231 (5)1.1781 (4)0.8579 (4)0.0926 (12)
H60.59511.26740.85800.111*
C70.4121 (4)1.1439 (3)0.9378 (4)0.0810 (10)
H70.40781.20680.99310.097*
C80.3070 (4)1.0102 (3)0.9311 (2)0.0587 (7)
N30.1071 (3)0.5575 (2)0.7327 (2)0.0622 (6)
H30.13640.63410.77170.075*0.50
N40.1163 (3)0.3728 (2)0.6582 (2)0.0627 (6)
H4A0.15440.31350.64290.075*
C90.3685 (3)0.5281 (2)0.7895 (2)0.0757 (9)
C100.1977 (3)0.4870 (3)0.7266 (2)0.0569 (7)
F80.3784 (12)0.5766 (11)0.8977 (4)0.130 (4)0.518 (14)
F90.4883 (7)0.6155 (10)0.7417 (9)0.163 (5)0.518 (14)
F100.4064 (9)0.4244 (5)0.8009 (8)0.105 (3)0.518 (14)
F8A0.4595 (8)0.4758 (11)0.7415 (10)0.161 (5)0.482 (14)
F9A0.4470 (9)0.6579 (3)0.7890 (10)0.117 (3)0.482 (14)
F10A0.3750 (11)0.5061 (12)0.9007 (4)0.135 (4)0.482 (14)
C11−0.0450 (4)0.4836 (3)0.6635 (2)0.0593 (7)
C12−0.0405 (4)0.3665 (3)0.6161 (2)0.0602 (7)
C13−0.1752 (4)0.2705 (3)0.5431 (3)0.0771 (9)
H13−0.17050.19300.51060.093*
C14−0.3154 (5)0.2961 (4)0.5213 (3)0.0897 (11)
H14−0.40980.23320.47430.108*
C15−0.3204 (5)0.4133 (5)0.5675 (3)0.0921 (11)
H15−0.41800.42700.54920.110*
C16−0.1879 (5)0.5100 (4)0.6388 (3)0.0786 (9)
H16−0.19260.58840.66900.094*
F10.8155 (16)0.8437 (14)0.8026 (9)0.191 (5)0.507 (14)
F20.9801 (12)0.8884 (13)0.6676 (9)0.164 (5)0.507 (14)
F30.7345 (11)0.8971 (12)0.6305 (8)0.131 (3)0.507 (14)
F40.9301 (13)1.0476 (8)0.7603 (10)0.175 (4)0.507 (14)
F1A0.8505 (12)0.8938 (8)0.8232 (5)0.105 (3)0.493 (14)
F2A1.0041 (11)0.9229 (11)0.6739 (11)0.123 (3)0.493 (14)
F3A0.7326 (12)0.8392 (17)0.6363 (9)0.208 (6)0.493 (14)
F4A0.875 (2)1.0469 (10)0.7068 (16)0.233 (6)0.493 (14)
B10.8652 (5)0.9202 (4)0.7116 (3)0.0835 (11)
O1W0.2248 (3)0.1817 (2)0.6036 (2)0.0972 (8)
H1A0.21320.17810.52990.146*
H1B0.15720.11310.62790.146*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F50.121 (2)0.1109 (18)0.1217 (19)−0.0148 (15)0.0434 (16)0.0023 (15)
F60.122 (2)0.165 (2)0.150 (2)0.0578 (18)0.0486 (17)0.103 (2)
F70.125 (2)0.139 (2)0.180 (3)0.0620 (17)0.098 (2)0.0385 (19)
N10.0647 (15)0.0599 (15)0.0577 (14)0.0281 (12)0.0147 (11)0.0044 (11)
N20.0804 (17)0.0739 (17)0.0576 (14)0.0435 (15)0.0091 (13)−0.0042 (13)
C10.081 (2)0.090 (3)0.085 (2)0.039 (2)0.032 (2)0.021 (2)
C20.0667 (18)0.0633 (19)0.0581 (17)0.0347 (15)0.0152 (14)0.0105 (14)
C30.0581 (17)0.0588 (17)0.0529 (16)0.0254 (14)0.0055 (13)0.0079 (13)
C40.074 (2)0.083 (2)0.0670 (19)0.0312 (19)0.0200 (16)0.0147 (17)
C50.076 (2)0.093 (3)0.093 (3)0.026 (2)0.0198 (19)0.035 (2)
C60.077 (2)0.067 (2)0.126 (3)0.0241 (19)−0.003 (2)0.028 (2)
C70.078 (2)0.059 (2)0.103 (3)0.0329 (18)−0.015 (2)−0.0030 (18)
C80.0611 (17)0.0600 (18)0.0571 (16)0.0299 (15)−0.0016 (14)0.0015 (14)
N30.0662 (15)0.0575 (14)0.0627 (14)0.0228 (13)0.0174 (12)0.0043 (11)
N40.0675 (16)0.0614 (15)0.0619 (14)0.0271 (12)0.0180 (12)0.0018 (12)
C90.066 (2)0.071 (2)0.084 (2)0.0213 (18)0.0118 (18)−0.0024 (19)
C100.0589 (17)0.0561 (17)0.0551 (16)0.0210 (14)0.0150 (13)0.0039 (13)
F80.117 (5)0.162 (7)0.106 (5)0.075 (6)−0.042 (4)−0.067 (4)
F90.061 (3)0.191 (8)0.237 (10)0.033 (5)0.047 (5)0.130 (8)
F100.078 (4)0.092 (3)0.151 (6)0.050 (3)−0.013 (3)−0.003 (3)
F8A0.065 (4)0.194 (10)0.207 (10)0.049 (6)0.009 (5)−0.090 (8)
F9A0.053 (4)0.098 (4)0.168 (7)0.000 (3)0.001 (3)0.018 (4)
F10A0.088 (4)0.198 (9)0.100 (5)0.033 (6)0.008 (4)0.068 (5)
C110.0651 (18)0.0645 (18)0.0503 (15)0.0260 (15)0.0143 (14)0.0116 (13)
C120.0653 (19)0.0672 (19)0.0472 (15)0.0237 (15)0.0153 (14)0.0080 (13)
C130.080 (2)0.082 (2)0.0578 (18)0.0223 (18)0.0085 (16)−0.0049 (16)
C140.078 (2)0.114 (3)0.062 (2)0.025 (2)0.0044 (17)0.002 (2)
C150.081 (3)0.135 (4)0.070 (2)0.054 (3)0.0062 (19)0.017 (2)
C160.085 (2)0.091 (2)0.072 (2)0.048 (2)0.0146 (19)0.0147 (18)
F10.141 (6)0.243 (10)0.136 (7)0.019 (8)0.012 (5)0.086 (8)
F20.181 (8)0.289 (13)0.104 (6)0.188 (10)0.009 (5)−0.012 (6)
F30.102 (5)0.214 (8)0.092 (4)0.093 (5)−0.016 (4)−0.020 (4)
F40.173 (7)0.131 (6)0.174 (8)0.018 (5)0.037 (6)−0.071 (5)
F1A0.134 (6)0.129 (5)0.060 (3)0.063 (5)0.018 (3)−0.015 (3)
F2A0.091 (4)0.140 (6)0.143 (8)0.039 (4)0.053 (5)0.031 (5)
F3A0.106 (5)0.339 (14)0.083 (4)−0.008 (7)0.013 (4)−0.018 (7)
F4A0.264 (14)0.170 (7)0.361 (18)0.151 (8)0.140 (12)0.133 (9)
B10.087 (3)0.095 (3)0.076 (3)0.043 (3)0.015 (2)0.010 (2)
O1W0.117 (2)0.0938 (18)0.0889 (17)0.0516 (15)0.0183 (15)−0.0090 (13)
Geometric parameters (Å, º) top
F5—C11.301 (4)C9—F8A1.306 (2)
F6—C11.305 (4)C9—F10A1.306 (2)
F7—C11.311 (4)C9—F81.307 (2)
N1—C21.312 (3)C9—F101.311 (2)
N1—C31.388 (4)C9—F9A1.312 (2)
N1—H10.8600C9—C101.471 (3)
N2—C21.331 (3)C11—C121.388 (4)
N2—C81.378 (4)C11—C161.398 (4)
N2—H2A0.8600C12—C131.384 (4)
C1—C21.475 (5)C13—C141.367 (5)
C3—C81.382 (4)C13—H130.9300
C3—C41.387 (4)C14—C151.386 (5)
C4—C51.371 (5)C14—H140.9300
C4—H40.9300C15—C161.369 (5)
C5—C61.385 (5)C15—H150.9300
C5—H50.9300C16—H160.9300
C6—C71.370 (5)F1—B11.368 (7)
C6—H60.9300F2—B11.332 (6)
C7—C81.379 (4)F3—B11.324 (7)
C7—H70.9300F4—B11.346 (7)
N3—C101.316 (3)F1A—B11.332 (7)
N3—C111.383 (4)F2A—B11.332 (7)
N3—H30.8600F3A—B11.332 (7)
N4—C101.329 (3)F4A—B11.361 (7)
N4—C121.380 (4)O1W—H1A0.8362
N4—H4A0.8600O1W—H1B0.8349
C9—F91.305 (2)
C2—N1—C3106.4 (2)F8A—C9—F9A106.1 (3)
C2—N1—H1126.8F10A—C9—F9A105.4 (3)
C3—N1—H1126.8F9—C9—C10116.2 (4)
C2—N2—C8108.2 (2)F8A—C9—C10114.7 (4)
C2—N2—H2A125.9F10A—C9—C10114.2 (5)
C8—N2—H2A125.9F8—C9—C10110.4 (4)
F5—C1—F6107.6 (3)F10—C9—C10110.7 (3)
F5—C1—F7106.9 (3)F9A—C9—C10108.2 (4)
F6—C1—F7105.5 (3)N3—C10—N4112.2 (2)
F5—C1—C2112.5 (3)N3—C10—C9124.2 (2)
F6—C1—C2112.1 (3)N4—C10—C9123.6 (2)
F7—C1—C2111.8 (3)N3—C11—C12108.4 (3)
N1—C2—N2111.6 (3)N3—C11—C16130.7 (3)
N1—C2—C1124.3 (3)C12—C11—C16120.9 (3)
N2—C2—C1124.0 (3)N4—C12—C13132.0 (3)
C8—C3—C4120.4 (3)N4—C12—C11105.6 (2)
C8—C3—N1108.3 (2)C13—C12—C11122.3 (3)
C4—C3—N1131.3 (3)C14—C13—C12116.3 (3)
C5—C4—C3117.0 (3)C14—C13—H13121.8
C5—C4—H4121.5C12—C13—H13121.8
C3—C4—H4121.5C13—C14—C15121.6 (3)
C4—C5—C6121.7 (3)C13—C14—H14119.2
C4—C5—H5119.2C15—C14—H14119.2
C6—C5—H5119.2C16—C15—C14122.9 (4)
C7—C6—C5122.2 (3)C16—C15—H15118.6
C7—C6—H6118.9C14—C15—H15118.6
C5—C6—H6118.9C15—C16—C11115.9 (3)
C6—C7—C8115.8 (3)C15—C16—H16122.0
C6—C7—H7122.1C11—C16—H16122.0
C8—C7—H7122.1F3—B1—F2111.2 (6)
N2—C8—C7131.5 (3)F2A—B1—F3A109.3 (8)
N2—C8—C3105.5 (2)F2A—B1—F1A115.8 (7)
C7—C8—C3123.0 (3)F3A—B1—F1A112.5 (7)
C10—N3—C11106.1 (2)F3—B1—F4110.9 (6)
C10—N3—H3126.9F2—B1—F4111.7 (7)
C11—N3—H3126.9F1A—B1—F482.7 (7)
C10—N4—C12107.6 (2)F2A—B1—F4A105.0 (7)
C10—N4—H4A126.2F3A—B1—F4A107.9 (8)
C12—N4—H4A126.2F1A—B1—F4A105.7 (7)
F8A—C9—F10A107.6 (4)F3—B1—F1109.8 (7)
F9—C9—F8107.6 (4)F2—B1—F1107.6 (7)
F9—C9—F10106.5 (3)F4—B1—F1105.4 (6)
F8—C9—F10104.6 (3)H1A—O1W—H1B112.4
C3—N1—C2—N2−0.3 (3)C12—N4—C10—C9178.8 (2)
C3—N1—C2—C1−178.0 (3)F9—C9—C10—N3−79.8 (7)
C8—N2—C2—N10.8 (3)F8A—C9—C10—N3−155.5 (8)
C8—N2—C2—C1178.5 (3)F10A—C9—C10—N379.6 (7)
F5—C1—C2—N1−33.5 (5)F8—C9—C10—N343.1 (6)
F6—C1—C2—N187.9 (4)F10—C9—C10—N3158.5 (5)
F7—C1—C2—N1−153.8 (3)F9A—C9—C10—N3−37.4 (6)
F5—C1—C2—N2149.1 (3)F9—C9—C10—N4101.1 (7)
F6—C1—C2—N2−89.5 (4)F8A—C9—C10—N425.4 (8)
F7—C1—C2—N228.8 (5)F10A—C9—C10—N4−99.4 (7)
C2—N1—C3—C8−0.3 (3)F8—C9—C10—N4−135.9 (6)
C2—N1—C3—C4179.1 (3)F10—C9—C10—N4−20.6 (6)
C8—C3—C4—C5−1.1 (4)F9A—C9—C10—N4143.6 (6)
N1—C3—C4—C5179.6 (3)C10—N3—C11—C12−0.1 (3)
C3—C4—C5—C60.3 (5)C10—N3—C11—C16179.6 (3)
C4—C5—C6—C70.9 (6)C10—N4—C12—C13−179.4 (3)
C5—C6—C7—C8−1.2 (5)C10—N4—C12—C110.3 (3)
C2—N2—C8—C7179.7 (3)N3—C11—C12—N4−0.1 (3)
C2—N2—C8—C3−0.9 (3)C16—C11—C12—N4−179.8 (3)
C6—C7—C8—N2179.8 (3)N3—C11—C12—C13179.6 (3)
C6—C7—C8—C30.4 (4)C16—C11—C12—C13−0.2 (4)
C4—C3—C8—N2−178.8 (3)N4—C12—C13—C14178.5 (3)
N1—C3—C8—N20.7 (3)C11—C12—C13—C14−1.1 (4)
C4—C3—C8—C70.7 (4)C12—C13—C14—C151.6 (5)
N1—C3—C8—C7−179.8 (3)C13—C14—C15—C16−1.0 (6)
C11—N3—C10—N40.3 (3)C14—C15—C16—C11−0.3 (5)
C11—N3—C10—C9−178.8 (2)N3—C11—C16—C15−178.9 (3)
C12—N4—C10—N3−0.4 (3)C12—C11—C16—C150.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O1W0.861.842.698 (3)177
N1—H1···N30.861.862.718 (3)175
N3—H3···N10.861.862.718 (3)175

Experimental details

Crystal data
Chemical formulaC8H6F3N2+·BF4−·C8H5F3N2·H2O
Mr478.11
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.7897 (18), 10.947 (2), 11.458 (2)
α, β, γ (°)92.48 (3), 96.59 (3), 113.34 (3)
V (Å3)1000.8 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.17
Crystal size (mm)0.36 × 0.32 × 0.28
Data collection
DiffractometerRigaku SCXmini
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.566, 0.640
No. of measured, independent and
observed [I > 2σ(I)] reflections		10445, 4581, 2280
Rint0.039
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.195, 1.03
No. of reflections4581
No. of parameters355
No. of restraints65
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.30, −0.21

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4A···O1W0.861.842.698 (3)177
N1—H1···N30.861.862.718 (3)175
N3—H3···N10.861.862.718 (3)175
 

Acknowledgements

The author thanks an anonymous advisor from the Ordered Matter Science Research Centre, Southeast University, for great help with the revision of this paper.

References

First citationFu, D. W., Zhang, W., Cai, H. L., Zhang, Y., Ge, J. Z., Xiong, R. G. & Huang, S. P. (2011). J. Am. Chem. Soc. 133, 12780–12786.  Web of Science CSD CrossRef CAS PubMed Google Scholar
 First citationLiu, M.-L. (2011a). Acta Cryst. E67, o2821.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationLiu, M.-L. (2011b). Acta Cryst. E67, o3473.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationLiu, M.-L. (2012). Acta Cryst. E68, o342.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationZhang, W., Chen, L. Z., Gou, M., Li, Y. H., Fu, D. W. & Xiong, R. G. (2010). Cryst. Growth Des. 10, 1025–1027.  Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Page o1076
doi:10.1107/S1600536812010847
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS