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Crystal structure of tetra­ethyl­ammonium chloride 3,4,5,6-tetra­fluoro-1,2-di­iodo­benzene

aDepartment of Chemistry, University of Ottawa, D'Iorio Hall, 10 Marie Curie Private, Ottawa, Ontario, K1N 6N5, Canada
*Correspondence e-mail: dbryce@uottawa.ca

Edited by T. N. Guru Row, Indian Institute of Science, India (Received 12 March 2015; accepted 13 April 2015; online 18 April 2015)

Equimolar qu­anti­ties of tetra­ethyl­ammonium chloride (Et4NCl) and 3,4,5,6-tetra­fluoro-1,2-di­iodo­benzene (o-DITFB or o-C6F4I2) have been co-crystallized in a solution of di­chloro­methane yielding a pure halogen-bonded compound, 3,4,5,6-tetra­fluoro-1,2-di­iodo­benzene–tetra­ethyl ammonium chloride (2/1), Et4N+·Cl·2C6F4I2, in the form of translucent needles. [(Et4NCl)(o-C6F4I2)2] packs in the C2/c space group. The asymmetric unit includes one mol­ecule of DITFB, one Et4N+ cation located on a twofold rotation axis, and one chloride anion also located on a twofold rotation symmetry axis. This compound has an inter­esting halogen-bonding environment surrounding the halide. Here, the chloride anion acts as a tetra­dentate halogen bond acceptor and forms a distorted square-pyramidal geometry, with I⋯Cl⋯I angles of 80.891 (6) and 78.811 (11)°, where two crystallographically distinct iodine atoms form halogen bonds with the chloride anion. Resulting from that square-pyramidal geometry are short contacts between some of the adjacent F atoms. Along the b axis, the halogen-bonding inter­action results in a polymeric network, producing a sheet in which the two closest chloride ions are 7.8931 (6) Å apart. The Et4N+ cation alternates in columns with the halide ion. The expected short contacts (shorter than the sum of their van der Waals radii) are observed for the halogen bonds [3.2191 (2) and 3.2968 (2) Å], as well as almost linear angles [170.953 (6) and 173.529 (6)°].

1. Related literature

The crystal structure of 3,4,5,6-tetra­fluoro-1,2-di­iodo­benzene has been recently published by our group (Viger-Gravel, Leclerc et al., 2014[Viger-Gravel, J., Leclerc, S., Korobkov, I. & Bryce, D. L. (2014). J. Am. Chem. Soc. 136, 6929-6942.]) and the crystal structure of Et4NCl was reported by Staples (1999[Staples, R. J. (1999). Z. Kristallogr. New Cryst. Struct. 214, 231-232.]). Reports by Abate et al. (2009[Abate, A., Biella, S., Cavallo, G., Meyer, F., Neukirch, H., Metrangolo, P., Pilati, T., Resnati, G. & Terraneo, G. (2009). J. Fluor. Chem. 130, 1171-1177.]), and our previous work (Viger-Gravel, Leclerc et al., 2014[Viger-Gravel, J., Leclerc, S., Korobkov, I. & Bryce, D. L. (2014). J. Am. Chem. Soc. 136, 6929-6942.]; Viger-Gravel, Meyer et al., 2014[Viger-Gravel, J., Meyer, J. E., Korobkov, I. & Bryce, D. L. (2014). CrystEngComm, 16, 7285-7297.]; Viger-Gravel et al., 2015[Viger-Gravel, J., Korobkov, I. & Bryce, D. L. (2015). Acta Cryst. E71, o286-o287.]) may be consulted for other similar halogen-bonded compounds containing o- or p-DITFB and ammonium halide salts. In these reports, halogen-bonding inter­actions are observed. Abate et al. discuss applications in crystal engineering. The latter reports describe the usefulness of solid-state nuclear magnetic resonance to characterize these types of halogen-bonding environments (Viger-Gravel, Leclerc et al., 2014[Viger-Gravel, J., Leclerc, S., Korobkov, I. & Bryce, D. L. (2014). J. Am. Chem. Soc. 136, 6929-6942.]; Viger-Gravel, Meyer et al., 2014[Viger-Gravel, J., Meyer, J. E., Korobkov, I. & Bryce, D. L. (2014). CrystEngComm, 16, 7285-7297.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C8H20N+·Cl·2C6F4I2

  • Mr = 969.42

  • Monoclinic, C 2/c

  • a = 7.8930 (6) Å

  • b = 16.8088 (13) Å

  • c = 20.9962 (16) Å

  • β = 97.803 (3)°

  • V = 2759.8 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 4.68 mm−1

  • T = 200 K

  • 0.23 × 0.18 × 0.08 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.555, Tmax = 0.746

  • 19329 measured reflections

  • 3445 independent reflections

  • 3260 reflections with I > 2σ(I)

  • Rint = 0.019

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.023

  • wR(F2) = 0.070

  • S = 1.02

  • 3445 reflections

  • 155 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −1.75 e Å−3

Table 1
Halogen-bonded geometry (Å, °)

C—XY XY C—XY YXY YXY
C1—I1⋯Cl3i 3.2968 (2) 173.529 (6) I1ii⋯Cl3⋯I2 80.891 (6)
C2—I2⋯Cl3 3.2191 (2) 170.953 (6) I2⋯Cl3⋯I1iii 78.811 (11)
Symmetry codes: (i) x + 1, y, z; (ii) 2 − x, y, [{3\over 2}] − z; (iii) −1 + x, y, z.

Table 2
Short contacts between hydrogen, DITFB or chloride (Å, °)

C—XZ F⋯Z C—F⋯Z
C3—F1⋯F4 2.532 (2) 166.944 (15)
C3—F1⋯F2 2.663 (3) 62.0647 (13)
C4—F2⋯F3 2.713 (2) 59.936 (12)
C5—F3⋯F4 2.671 (2) 60.201 (13)
C3—F1⋯C2 2.364 (3) 30.165 (12)
C3—F1⋯H8Bi 2.614 (2) 100.233 (14)
C4—F2⋯H10Bii 2.570 (2) 165.27 (2)
C10—H10C⋯Cl3iii 2.936 (2) 148.5 (2)
Symmetry codes: (i) x − [{1\over 2}], y − [{1\over 2}], z; (ii) −x + [{3\over 2}], −y + [{3\over 2}], −z + 1; (iii) −x + 1, y − 1, −z + [{3\over 2}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2009[Bruker (2009). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Experimental top

Data collection results for [(Et4NCl)(o-C6F4I2)] represent the best data set obtained in several trials. The crystal was mounted on a thin glass fiber using paraffin oil. Prior to data collection, crystals were cooled to 200.15 °K. Data were collected on a Bruker AXS SMART single crystal diffractometer equipped with a sealed Mo tube source (wavelength 0.71073 Å) APEX II CCD detector. Raw data collection and processing were performed with the APEX II software package (Bruker, 2009). Diffraction data were collected with a sequence of 0.3° ω scans at 0, 120, and 240° in φ. Due to lower symmetry in order to ensure adequate data completeness and redundancy the initial unit cell parameters were determined from 60 data frames with 0.3° ω scan each collected at the different sections of the Ewald sphere. Semi-empirical absorption corrections based on equivalent reflections were applied.

Refinement details top

Systematic absences in the diffraction data set and unit cell parameters were consistent with the monoclinic C2/c (No.15) space group for [(Et4NCl)(o-C6F4I2)]. The solution in the centrosymmetric space group yielded chemically reasonable and computationally stable results of refinement. The structure was solved by direct methods, completed with difference Fourier synthesis, and refined with full-matrix least-squares procedures based on F2.

The structural model for [(Et4NCl)(o-C6F4I2)] contains one ammonium cation and one chlorine atom located on two different two-fold axis symmetry elements of the space group while aromatic molecules are located in general positions.

In this structural model, the hydrogen atom positions were located from the differences in Fourier maps. However, after initial positioning, all hydrogen atomic positions were constrained to suitable geometries and subsequently treated as idealized contributions. All scattering factors are contained in several versions of the SHELXTL program library, with the latest version used being v.6.12 (Sheldrick, 2008).

Related literature top

The crystal structure of 3,4,5,6-tetrafluoro-1,2-diiodobenzene has been recently published by our group (Viger-Gravel et al., 2015) and the crystal structure of Et4NCl was reported by Staples (1999). Reports by Abate et al. (2009), and our previous work (Viger-Gravel, Leclerc et al., 2014; Viger-Gravel, Meyer et al., 2014) may be consulted for other similar halogen-bonded compounds containing o- or p-DITFB and ammonium halide salts. In both reports, halogen-bonding interactions are observed. Abate et al. discuss applications in crystal engineering. The latter reports describe the usefulness of solid-state nuclear magnetic resonance to characterize these types of halogen-bonding environments (Viger-Gravel, Leclerc et al., 2014; Viger-Gravel, Meyer et al., 2014).

Structure description top

Data collection results for [(Et4NCl)(o-C6F4I2)] represent the best data set obtained in several trials. The crystal was mounted on a thin glass fiber using paraffin oil. Prior to data collection, crystals were cooled to 200.15 °K. Data were collected on a Bruker AXS SMART single crystal diffractometer equipped with a sealed Mo tube source (wavelength 0.71073 Å) APEX II CCD detector. Raw data collection and processing were performed with the APEX II software package (Bruker, 2009). Diffraction data were collected with a sequence of 0.3° ω scans at 0, 120, and 240° in φ. Due to lower symmetry in order to ensure adequate data completeness and redundancy the initial unit cell parameters were determined from 60 data frames with 0.3° ω scan each collected at the different sections of the Ewald sphere. Semi-empirical absorption corrections based on equivalent reflections were applied.

The crystal structure of 3,4,5,6-tetrafluoro-1,2-diiodobenzene has been recently published by our group (Viger-Gravel et al., 2015) and the crystal structure of Et4NCl was reported by Staples (1999). Reports by Abate et al. (2009), and our previous work (Viger-Gravel, Leclerc et al., 2014; Viger-Gravel, Meyer et al., 2014) may be consulted for other similar halogen-bonded compounds containing o- or p-DITFB and ammonium halide salts. In both reports, halogen-bonding interactions are observed. Abate et al. discuss applications in crystal engineering. The latter reports describe the usefulness of solid-state nuclear magnetic resonance to characterize these types of halogen-bonding environments (Viger-Gravel, Leclerc et al., 2014; Viger-Gravel, Meyer et al., 2014).

Refinement details top

Systematic absences in the diffraction data set and unit cell parameters were consistent with the monoclinic C2/c (No.15) space group for [(Et4NCl)(o-C6F4I2)]. The solution in the centrosymmetric space group yielded chemically reasonable and computationally stable results of refinement. The structure was solved by direct methods, completed with difference Fourier synthesis, and refined with full-matrix least-squares procedures based on F2.

The structural model for [(Et4NCl)(o-C6F4I2)] contains one ammonium cation and one chlorine atom located on two different two-fold axis symmetry elements of the space group while aromatic molecules are located in general positions.

In this structural model, the hydrogen atom positions were located from the differences in Fourier maps. However, after initial positioning, all hydrogen atomic positions were constrained to suitable geometries and subsequently treated as idealized contributions. All scattering factors are contained in several versions of the SHELXTL program library, with the latest version used being v.6.12 (Sheldrick, 2008).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT (Bruker, 2009); data reduction: SAINT and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Halogen-bonding interactions in [(Et4NCl)(o-C6F4I2)], where iodine is in purple, carbon in black, fluorine in green, and chloride in blue. Short type I fluorine–fluorine contacts are also shown.
[Figure 2] Fig. 2. 2 x 2 x 2 supercell of [(Et4NCl)(o-DITFB)] along the a axis in (a). Along the a axis, rows of alternating halogen-bonded complexes and cations are easily observed. In (b) is presented the network formed in the ac plane where the closest anions are 7.8931 Å apart. The color legend used is: iodine in purple, carbon in black, fluorine in green, and chloride in blue.
3,4,5,6-Tetrafluoro-1,2-diiodobenzene–tetraethyl ammonium chloride (2/1) top
Crystal data top
C8H20N+·Cl·2C6F4I2F(000) = 1792
Mr = 969.42Dx = 2.333 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 7.8930 (6) ÅCell parameters from 9886 reflections
b = 16.8088 (13) Åθ = 2.4–28.3°
c = 20.9962 (16) ŵ = 4.68 mm1
β = 97.803 (3)°T = 200 K
V = 2759.8 (4) Å3Plate, colourless
Z = 40.23 × 0.18 × 0.08 mm
Data collection top
Bruker APEXII CCD
diffractometer
3260 reflections with I > 2σ(I)
φ and ω scansRint = 0.019
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
θmax = 28.3°, θmin = 2.4°
Tmin = 0.555, Tmax = 0.746h = 1010
19329 measured reflectionsk = 2122
3445 independent reflectionsl = 2727
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.023H-atom parameters constrained
wR(F2) = 0.070 w = 1/[σ2(Fo2) + (0.0482P)2 + 4.146P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.004
3445 reflectionsΔρmax = 0.31 e Å3
155 parametersΔρmin = 1.75 e Å3
Crystal data top
C8H20N+·Cl·2C6F4I2V = 2759.8 (4) Å3
Mr = 969.42Z = 4
Monoclinic, C2/cMo Kα radiation
a = 7.8930 (6) ŵ = 4.68 mm1
b = 16.8088 (13) ÅT = 200 K
c = 20.9962 (16) Å0.23 × 0.18 × 0.08 mm
β = 97.803 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
3445 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3260 reflections with I > 2σ(I)
Tmin = 0.555, Tmax = 0.746Rint = 0.019
19329 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0230 restraints
wR(F2) = 0.070H-atom parameters constrained
S = 1.02Δρmax = 0.31 e Å3
3445 reflectionsΔρmin = 1.75 e Å3
155 parameters
Special details top

Experimental. Data collection is performed with three batch runs at phi = 0.00 ° (650 frames), at phi = 120.00 ° (650 frames), and at phi = 240.00 ° (650 frames). Frame width = 0.30 ° in omega. Data is merged, corrected for decay (if any), and treated with multi-scan absorption corrections (if required). All symmetry-equivalent reflections are merged for centrosymmetric data. Friedel pairs are not merged for noncentrosymmetric data.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I11.20603 (2)0.23394 (2)0.64245 (2)0.03195 (7)
I20.73344 (2)0.23667 (2)0.65441 (2)0.03262 (7)
Cl30.50000.15395 (5)0.75000.03270 (17)
F10.57429 (19)0.34488 (13)0.54284 (9)0.0488 (4)
F20.6984 (2)0.43431 (12)0.45505 (9)0.0548 (5)
F31.0382 (2)0.43372 (12)0.44632 (9)0.0552 (5)
F41.2508 (2)0.34428 (14)0.52645 (10)0.0551 (5)
N11.00000.98253 (15)0.75000.0303 (6)
C11.0245 (3)0.29692 (14)0.57959 (11)0.0285 (4)
C20.8494 (3)0.29779 (14)0.58425 (11)0.0281 (4)
C30.7436 (3)0.34314 (17)0.54106 (12)0.0325 (5)
C40.8050 (3)0.38943 (16)0.49509 (12)0.0363 (5)
C50.9761 (3)0.38863 (16)0.49051 (13)0.0372 (5)
C61.0838 (3)0.34232 (17)0.53238 (13)0.0347 (5)
C71.0674 (4)1.03725 (15)0.70149 (13)0.0378 (5)
H7A0.97251.07150.68180.045*
H7B1.15581.07230.72470.045*
C81.1435 (5)0.9949 (2)0.64821 (18)0.0577 (9)
H8A1.18311.03430.61920.087*
H8B1.05640.96090.62410.087*
H8C1.24030.96210.66690.087*
C90.8599 (4)0.92855 (16)0.71801 (15)0.0401 (6)
H9A0.90770.89540.68580.048*
H9B0.82460.89220.75100.048*
C100.7022 (4)0.9708 (2)0.68505 (18)0.0525 (8)
H10A0.61910.93130.66580.079*
H10B0.73441.00580.65140.079*
H10C0.65111.00250.71670.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02594 (10)0.03161 (11)0.03700 (11)0.00044 (5)0.00040 (7)0.00317 (6)
I20.02988 (10)0.03613 (12)0.03308 (11)0.00047 (6)0.00879 (7)0.00037 (6)
Cl30.0309 (4)0.0339 (4)0.0335 (4)0.0000.0050 (3)0.000
F10.0244 (7)0.0691 (12)0.0524 (10)0.0085 (7)0.0034 (7)0.0081 (9)
F20.0482 (10)0.0664 (12)0.0472 (10)0.0187 (9)0.0025 (8)0.0198 (9)
F30.0542 (11)0.0637 (11)0.0490 (10)0.0016 (9)0.0122 (8)0.0254 (9)
F40.0261 (8)0.0771 (13)0.0631 (12)0.0022 (8)0.0100 (7)0.0259 (10)
N10.0397 (15)0.0185 (12)0.0328 (15)0.0000.0047 (12)0.000
C10.0250 (10)0.0298 (11)0.0297 (11)0.0006 (8)0.0001 (8)0.0006 (9)
C20.0260 (10)0.0312 (11)0.0270 (11)0.0016 (9)0.0033 (8)0.0041 (9)
C30.0246 (10)0.0398 (13)0.0325 (12)0.0029 (9)0.0014 (9)0.0021 (10)
C40.0347 (12)0.0411 (13)0.0309 (12)0.0066 (10)0.0030 (9)0.0037 (11)
C50.0383 (13)0.0404 (13)0.0330 (13)0.0019 (11)0.0053 (10)0.0081 (11)
C60.0257 (11)0.0416 (14)0.0370 (13)0.0016 (10)0.0047 (9)0.0038 (11)
C70.0503 (15)0.0278 (11)0.0364 (13)0.0003 (11)0.0104 (11)0.0044 (10)
C80.077 (2)0.0514 (18)0.0494 (19)0.0087 (17)0.0271 (17)0.0018 (15)
C90.0433 (14)0.0279 (12)0.0472 (15)0.0045 (10)0.0004 (11)0.0066 (11)
C100.0464 (16)0.0472 (16)0.060 (2)0.0030 (14)0.0062 (14)0.0076 (15)
Geometric parameters (Å, º) top
I1—C12.098 (2)N1—C7i1.521 (3)
I2—C22.105 (2)C1—C61.382 (3)
F1—C31.342 (3)C1—C21.398 (3)
F2—C41.339 (3)C2—C31.377 (3)
F3—C51.341 (3)C3—C41.378 (4)
F4—C61.341 (3)C4—C51.367 (4)
N1—C9i1.515 (3)C5—C61.378 (4)
N1—C91.515 (3)C7—C81.517 (4)
N1—C71.521 (3)C9—C101.516 (4)
C9i—N1—C9106.4 (3)F1—C3—C4117.0 (2)
C9i—N1—C7111.01 (16)C2—C3—C4122.3 (2)
C9—N1—C7111.46 (16)F2—C4—C5120.3 (2)
C9i—N1—C7i111.45 (16)F2—C4—C3120.5 (2)
C9—N1—C7i111.01 (16)C5—C4—C3119.2 (2)
C7—N1—C7i105.6 (3)F3—C5—C4120.0 (2)
C6—C1—C2118.6 (2)F3—C5—C6120.6 (2)
C6—C1—I1117.43 (17)C4—C5—C6119.4 (2)
C2—C1—I1123.94 (18)F4—C6—C5117.1 (2)
C3—C2—C1118.5 (2)F4—C6—C1120.9 (2)
C3—C2—I2116.65 (17)C5—C6—C1122.0 (2)
C1—C2—I2124.86 (18)C8—C7—N1114.8 (2)
F1—C3—C2120.7 (2)C10—C9—N1115.3 (2)
C6—C1—C2—C30.8 (4)C3—C4—C5—C60.7 (4)
I1—C1—C2—C3178.32 (18)F3—C5—C6—F40.4 (4)
C6—C1—C2—I2177.65 (19)C4—C5—C6—F4179.2 (3)
I1—C1—C2—I20.1 (3)F3—C5—C6—C1178.2 (3)
C1—C2—C3—F1178.8 (2)C4—C5—C6—C10.7 (4)
I2—C2—C3—F12.6 (3)C2—C1—C6—F4179.2 (2)
C1—C2—C3—C42.2 (4)I1—C1—C6—F41.4 (4)
I2—C2—C3—C4176.4 (2)C2—C1—C6—C50.6 (4)
F1—C3—C4—F20.8 (4)I1—C1—C6—C5177.1 (2)
C2—C3—C4—F2178.2 (2)C9i—N1—C7—C858.5 (3)
F1—C3—C4—C5178.8 (3)C9—N1—C7—C860.0 (3)
C2—C3—C4—C52.2 (4)C7i—N1—C7—C8179.4 (3)
F2—C4—C5—F30.9 (4)C9i—N1—C9—C10177.6 (3)
C3—C4—C5—F3179.6 (3)C7—N1—C9—C1061.2 (3)
F2—C4—C5—C6179.7 (3)C7i—N1—C9—C1056.2 (3)
Symmetry code: (i) x+2, y, z+3/2.
Halogen-bonded geometry (Å, °) top
C—X···YX···YC—X···YY···X···YY···X···Y
C1—I1···Cl3i3.2968 (2)173.529 (6)I1ii···Cl3···I280.891 (6)
C2—I2···Cl33.2191 (2)170.953 (6)I2···Cl3···I1iii78.811 (11)
Symmetry codes: (i) x + 1, y, z; (ii) 2 - x, y, 3/2 - z; (iii) -1 + x, y, z.
Short contacts between hydrogen, DITFB or chloride (Å, °) top
C—X···ZF···ZC—F···Z
C3—F1···F42.5321 (22)166.944 (15)
C3—F1···F22.6625 (28)62.0647 (13)
C4—F2···F32.7129 (23)59.936 (12)
C5—F3···F42.6709 (24)60.201 (13)
C3—F1···C22.3637 (27)30.165 (12)
C3—F1···H8Bi2.6137 (19)100.233 (14)
C4—F2···H10Bii2.5702 (21)165.268 (23)
C10—H10C···Cl3iii2.9363 (2)148.447 (201)
Symmetry codes: (i) x - 1/2, y - 1/2, z; (ii) -x + 3/2, -y + 3/2, -z + 1; (iii) -x + 1, y - 1, -z + 3/2.
 

Acknowledgements

DLB thanks the Natural Sciences and Engineering Research Council (NSERC) of Canada for funding and JVG thanks the Fonds de Recherche du Québec – Nature et Technologies (FRQNT) for a scholarship.

References

First citationAbate, A., Biella, S., Cavallo, G., Meyer, F., Neukirch, H., Metrangolo, P., Pilati, T., Resnati, G. & Terraneo, G. (2009). J. Fluor. Chem. 130, 1171–1177.  Web of Science CSD CrossRef CAS Google Scholar
First citationBruker (2009). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationStaples, R. J. (1999). Z. Kristallogr. New Cryst. Struct. 214, 231–232.  CAS Google Scholar
First citationViger-Gravel, J., Korobkov, I. & Bryce, D. L. (2015). Acta Cryst. E71, o286–o287.  CSD CrossRef IUCr Journals Google Scholar
First citationViger-Gravel, J., Leclerc, S., Korobkov, I. & Bryce, D. L. (2014). J. Am. Chem. Soc. 136, 6929–6942.  Web of Science CAS PubMed Google Scholar
First citationViger-Gravel, J., Meyer, J. E., Korobkov, I. & Bryce, D. L. (2014). CrystEngComm, 16, 7285–7297.  CAS Google Scholar

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