It is possible that fluorous compounds could be utilized as directing forces in crystal engineering for applications in materials chemistry or catalysis. Although numerous fluorous compounds have been used for various applications, their structures in the solid state remains a lively matter for debate. The reaction of 4-[(2,2,2-trifluoroethoxy)methyl]pyridine with H
X (
X = I or Cl) yielded new fluorous ponytailed pyridinium halide salts, namely 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium iodide, C
8H
9F
3NO
+·I
−, (1), and 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium chloride, C
8H
9F
3NO
+·Cl
−, (2), which were characterized by IR spectroscopy, multinuclei (
1H,
13C and
19F) NMR spectroscopy and single-crystal X-ray diffraction. Structure analysis showed that there are two types of hydrogen bonds, namely N—H
X and C—H
X. The iodide anion in salt (1) is hydrogen bonded to three 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium cations in the crystal packing, while the chloride ion in salt (2) is involved in six hydrogen bonds to five 4-[(2,2,2-trifluoroethoxy)methyl]pyridinium cations, which is attributed to the smaller size and reduced polarizability of the chloride ion compared to the iodide ion. In the IR spectra, the pyridinium N—H stretching band for salt (1) exhibited a blue shift compared with that of salt (2).
Supporting information
CCDC references: 1517711; 1517710
For both compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: shelXle (Hübschle et al., 2011) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015b) and WinGX (Farrugia, 2012).
(i16196) 4-[(2,2,2-Trifluoroethoxy)methyl]pyridinium iodide
top
Crystal data top
C8H9F3NO+·I− | F(000) = 608 |
Mr = 319.06 | Dx = 2.005 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8651 (3) Å | Cell parameters from 9913 reflections |
b = 9.2595 (3) Å | θ = 2.6–27.3° |
c = 14.7958 (5) Å | µ = 3.04 mm−1 |
β = 101.151 (1)° | T = 100 K |
V = 1057.19 (6) Å3 | Prism, colourless |
Z = 4 | 0.44 × 0.3 × 0.22 mm |
Data collection top
Bruker APEXII CCD diffractometer | 2325 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.026 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 27.1°, θmin = 2.6° |
Tmin = 0.673, Tmax = 0.971 | h = −10→10 |
41459 measured reflections | k = −11→11 |
2334 independent reflections | l = −18→18 |
Refinement top
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.012 | w = 1/[σ2(Fo2) + (0.005P)2 + 0.8874P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.028 | (Δ/σ)max = 0.002 |
S = 1.21 | Δρmax = 0.37 e Å−3 |
2334 reflections | Δρmin = −0.26 e Å−3 |
164 parameters | Extinction correction: SHELXL2013 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0084 (3) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
I1 | 0.55550 (2) | 0.18787 (2) | 0.60106 (2) | 0.01697 (5) | |
F1 | 0.53198 (12) | 0.89861 (11) | 0.14989 (7) | 0.0263 (2) | |
F2 | 0.25938 (12) | 0.90209 (10) | 0.09319 (8) | 0.0277 (2) | |
F3 | 0.44127 (15) | 0.84459 (11) | 0.00801 (7) | 0.0299 (2) | |
O1 | 0.55327 (13) | 0.61073 (11) | 0.11764 (7) | 0.0164 (2) | |
N1 | 0.57467 (18) | 0.25969 (17) | 0.37582 (10) | 0.0235 (3) | |
C1 | 0.5954 (2) | 0.4026 (2) | 0.37325 (11) | 0.0222 (3) | |
C2 | 0.58878 (19) | 0.47115 (18) | 0.29023 (10) | 0.0171 (3) | |
C3 | 0.55746 (18) | 0.39042 (16) | 0.20962 (10) | 0.0143 (3) | |
C4 | 0.5348 (2) | 0.24154 (17) | 0.21537 (11) | 0.0202 (3) | |
C5 | 0.5452 (2) | 0.17803 (19) | 0.29976 (12) | 0.0241 (3) | |
C6 | 0.5508 (2) | 0.45735 (16) | 0.11656 (10) | 0.0167 (3) | |
C7 | 0.3901 (2) | 0.67462 (16) | 0.11850 (11) | 0.0166 (3) | |
C8 | 0.4061 (2) | 0.83010 (16) | 0.09243 (11) | 0.0175 (3) | |
H1A | 0.578 (3) | 0.221 (3) | 0.4284 (17) | 0.041 (6)* | |
H1 | 0.614 (2) | 0.453 (2) | 0.4302 (14) | 0.024 (5)* | |
H2 | 0.602 (2) | 0.569 (2) | 0.2885 (12) | 0.017 (4)* | |
H4 | 0.515 (3) | 0.183 (2) | 0.1622 (15) | 0.029 (5)* | |
H5 | 0.531 (3) | 0.078 (2) | 0.3074 (14) | 0.028 (5)* | |
H6A | 0.655 (2) | 0.425 (2) | 0.0941 (12) | 0.017 (4)* | |
H6B | 0.449 (2) | 0.423 (2) | 0.0749 (13) | 0.019 (5)* | |
H7A | 0.359 (2) | 0.673 (2) | 0.1800 (14) | 0.022 (5)* | |
H7B | 0.295 (3) | 0.630 (2) | 0.0728 (13) | 0.023 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.02272 (7) | 0.01525 (6) | 0.01325 (6) | −0.00010 (4) | 0.00425 (4) | 0.00119 (3) |
F1 | 0.0203 (5) | 0.0203 (5) | 0.0367 (6) | −0.0055 (4) | 0.0016 (4) | −0.0077 (4) |
F2 | 0.0193 (5) | 0.0188 (5) | 0.0444 (6) | 0.0059 (4) | 0.0050 (4) | 0.0007 (4) |
F3 | 0.0487 (7) | 0.0203 (5) | 0.0239 (5) | 0.0018 (5) | 0.0150 (5) | 0.0079 (4) |
O1 | 0.0152 (5) | 0.0132 (5) | 0.0218 (5) | 0.0014 (4) | 0.0059 (4) | 0.0046 (4) |
N1 | 0.0192 (7) | 0.0352 (8) | 0.0176 (7) | 0.0087 (6) | 0.0076 (5) | 0.0127 (6) |
C1 | 0.0159 (7) | 0.0349 (9) | 0.0159 (7) | 0.0039 (7) | 0.0037 (6) | −0.0003 (7) |
C2 | 0.0154 (7) | 0.0196 (8) | 0.0165 (7) | 0.0020 (6) | 0.0037 (6) | −0.0011 (6) |
C3 | 0.0110 (6) | 0.0169 (7) | 0.0153 (7) | 0.0026 (5) | 0.0034 (5) | 0.0019 (5) |
C4 | 0.0239 (8) | 0.0166 (7) | 0.0203 (8) | 0.0022 (6) | 0.0047 (6) | 0.0020 (6) |
C5 | 0.0238 (8) | 0.0213 (8) | 0.0288 (9) | 0.0042 (7) | 0.0085 (7) | 0.0094 (7) |
C6 | 0.0230 (8) | 0.0132 (7) | 0.0146 (7) | 0.0021 (6) | 0.0051 (6) | 0.0009 (5) |
C7 | 0.0144 (7) | 0.0160 (7) | 0.0198 (7) | 0.0002 (6) | 0.0044 (6) | 0.0022 (6) |
C8 | 0.0165 (7) | 0.0166 (7) | 0.0194 (7) | −0.0001 (6) | 0.0034 (6) | −0.0010 (6) |
Geometric parameters (Å, º) top
F1—C8 | 1.3341 (18) | C2—H2 | 0.91 (2) |
F2—C8 | 1.3346 (18) | C3—C4 | 1.395 (2) |
F3—C8 | 1.3373 (18) | C3—C6 | 1.502 (2) |
O1—C7 | 1.4154 (18) | C4—C5 | 1.368 (2) |
O1—C6 | 1.4204 (18) | C4—H4 | 0.94 (2) |
N1—C1 | 1.335 (2) | C5—H5 | 0.95 (2) |
N1—C5 | 1.338 (2) | C6—H6A | 0.985 (18) |
N1—H1A | 0.85 (2) | C6—H6B | 0.964 (19) |
C1—C2 | 1.374 (2) | C7—C8 | 1.502 (2) |
C1—H1 | 0.95 (2) | C7—H7A | 0.99 (2) |
C2—C3 | 1.389 (2) | C7—H7B | 1.00 (2) |
| | | |
C7—O1—C6 | 114.06 (12) | O1—C6—C3 | 113.85 (12) |
C1—N1—C5 | 122.58 (15) | O1—C6—H6A | 107.3 (11) |
C1—N1—H1A | 117.5 (16) | C3—C6—H6A | 107.5 (11) |
C5—N1—H1A | 119.9 (16) | O1—C6—H6B | 110.1 (11) |
N1—C1—C2 | 119.96 (15) | C3—C6—H6B | 109.1 (11) |
N1—C1—H1 | 117.2 (12) | H6A—C6—H6B | 108.8 (15) |
C2—C1—H1 | 122.9 (12) | O1—C7—C8 | 106.09 (12) |
C1—C2—C3 | 119.27 (15) | O1—C7—H7A | 113.0 (11) |
C1—C2—H2 | 119.9 (12) | C8—C7—H7A | 107.3 (11) |
C3—C2—H2 | 120.8 (12) | O1—C7—H7B | 112.7 (11) |
C2—C3—C4 | 118.89 (14) | C8—C7—H7B | 108.2 (11) |
C2—C3—C6 | 122.30 (14) | H7A—C7—H7B | 109.3 (16) |
C4—C3—C6 | 118.79 (14) | F1—C8—F2 | 107.07 (12) |
C5—C4—C3 | 119.65 (16) | F1—C8—F3 | 106.59 (13) |
C5—C4—H4 | 119.1 (13) | F2—C8—F3 | 107.05 (13) |
C3—C4—H4 | 121.2 (13) | F1—C8—C7 | 112.38 (13) |
N1—C5—C4 | 119.64 (16) | F2—C8—C7 | 111.16 (13) |
N1—C5—H5 | 117.4 (12) | F3—C8—C7 | 112.26 (13) |
C4—C5—H5 | 122.9 (12) | | |
Hydrogen-bond geometry (Å, º) top(a) a synthon hydrogen bond and (b) a bifurcated hydrogen bond. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···I1 | 0.85 (3) | 2.61 (2) | 3.430 (1) | 161 (2) |
C2—H2···I1i | 0.91 (2) | 3.17 (2) | 3.814 (2) | 129 (1) |
C5—H5···I1ii | 0.94 (2) | 2.95 (2) | 3.835 (2) | 157 (2) |
C4—H4···F1iii | 0.94 (2) | 2.65 (2) | 3.319 (2) | 129 (2) |
C4—H4···F3iv | 0.94 (2) | 2.62 (2) | 3.440 (2) | 146 (2) |
C8—F1···C1v | 1.33 (1) | 3.02 (1) | | 124 (1) |
C8—F1···C2v | 1.33 (1) | 3.02 (1) | | 150 (1) |
C8—F2···C1vi | 1.34 (1) | 2.93 (1) | | 149 (1) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x, y−1, z; (iv) −x+1, −y+1, −z; (v) −x+3/2, y+1/2, −z+1/2; (vi) −x+1/2, y+1/2, −z+1/2. |
(i16195) 4-[(2,2,2-Trifluoroethoxy)methyl]pyridinium chloride
top
Crystal data top
C8H9F3NO+·Cl− | Dx = 1.523 Mg m−3 |
Mr = 227.61 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 9946 reflections |
a = 9.2236 (3) Å | θ = 2.6–26.1° |
b = 13.5704 (5) Å | µ = 0.40 mm−1 |
c = 15.8600 (5) Å | T = 100 K |
V = 1985.16 (12) Å3 | Prism, colourless |
Z = 8 | 0.22 × 0.18 × 0.12 mm |
F(000) = 928 | |
Data collection top
Bruker APEXII CCD diffractometer | 1927 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.050 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 27.1°, θmin = 2.6° |
Tmin = 0.922, Tmax = 0.971 | h = −11→11 |
63957 measured reflections | k = −17→17 |
2189 independent reflections | l = −20→20 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.025 | All H-atom parameters refined |
wR(F2) = 0.064 | w = 1/[σ2(Fo2) + (0.0255P)2 + 1.0937P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2189 reflections | Δρmax = 0.28 e Å−3 |
163 parameters | Δρmin = −0.23 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.05957 (3) | −0.15913 (2) | −0.10192 (2) | 0.01914 (9) | |
F1 | 0.62467 (11) | 0.35557 (6) | 0.09652 (5) | 0.0328 (2) | |
F2 | 0.68077 (8) | 0.40956 (6) | 0.21971 (5) | 0.02548 (19) | |
F3 | 0.45867 (9) | 0.37504 (6) | 0.19017 (6) | 0.0309 (2) | |
O1 | 0.53248 (10) | 0.18040 (7) | 0.16109 (6) | 0.0213 (2) | |
N1 | 0.26627 (12) | −0.08440 (8) | 0.02742 (7) | 0.0177 (2) | |
C1 | 0.39350 (14) | −0.12504 (10) | 0.04880 (8) | 0.0185 (3) | |
C2 | 0.48867 (14) | −0.07384 (9) | 0.09915 (8) | 0.0173 (3) | |
C3 | 0.45331 (13) | 0.02072 (9) | 0.12647 (7) | 0.0159 (2) | |
C4 | 0.31866 (14) | 0.05944 (9) | 0.10412 (8) | 0.0180 (3) | |
C5 | 0.22692 (14) | 0.00532 (10) | 0.05434 (8) | 0.0193 (3) | |
C6 | 0.55635 (14) | 0.07928 (9) | 0.17978 (8) | 0.0183 (3) | |
C7 | 0.62181 (14) | 0.24287 (9) | 0.20975 (8) | 0.0171 (3) | |
C8 | 0.59554 (14) | 0.34516 (9) | 0.17858 (8) | 0.0194 (3) | |
H1A | 0.2052 (19) | −0.1167 (13) | −0.0078 (11) | 0.037 (5)* | |
H1 | 0.4144 (16) | −0.1877 (11) | 0.0281 (9) | 0.019 (4)* | |
H2 | 0.5773 (16) | −0.1027 (11) | 0.1124 (9) | 0.020 (4)* | |
H4 | 0.2881 (16) | 0.1212 (12) | 0.1221 (9) | 0.022 (4)* | |
H5 | 0.1349 (17) | 0.0282 (11) | 0.0377 (9) | 0.021 (4)* | |
H6A | 0.5379 (15) | 0.0666 (11) | 0.2397 (10) | 0.020 (4)* | |
H6B | 0.6549 (18) | 0.0616 (11) | 0.1670 (9) | 0.023 (4)* | |
H7A | 0.7214 (16) | 0.2299 (10) | 0.2016 (8) | 0.017 (4)* | |
H7B | 0.5952 (15) | 0.2414 (11) | 0.2692 (9) | 0.017 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.01730 (16) | 0.01961 (16) | 0.02051 (16) | −0.00136 (11) | −0.00131 (11) | −0.00397 (11) |
F1 | 0.0531 (6) | 0.0259 (5) | 0.0194 (4) | −0.0062 (4) | 0.0023 (4) | 0.0056 (3) |
F2 | 0.0275 (4) | 0.0185 (4) | 0.0304 (4) | −0.0073 (3) | 0.0003 (3) | −0.0042 (3) |
F3 | 0.0222 (4) | 0.0228 (4) | 0.0477 (5) | 0.0047 (3) | −0.0028 (4) | −0.0005 (4) |
O1 | 0.0270 (5) | 0.0121 (4) | 0.0247 (5) | −0.0027 (4) | −0.0091 (4) | 0.0009 (4) |
N1 | 0.0181 (5) | 0.0170 (5) | 0.0180 (5) | −0.0030 (4) | −0.0020 (4) | 0.0003 (4) |
C1 | 0.0230 (6) | 0.0148 (6) | 0.0178 (6) | 0.0017 (5) | 0.0007 (5) | 0.0003 (5) |
C2 | 0.0176 (6) | 0.0165 (6) | 0.0179 (6) | 0.0029 (5) | −0.0008 (5) | 0.0022 (5) |
C3 | 0.0190 (6) | 0.0156 (6) | 0.0129 (5) | −0.0014 (5) | 0.0015 (5) | 0.0025 (5) |
C4 | 0.0189 (6) | 0.0143 (6) | 0.0207 (6) | 0.0019 (5) | 0.0016 (5) | 0.0001 (5) |
C5 | 0.0158 (6) | 0.0198 (6) | 0.0223 (6) | 0.0013 (5) | 0.0006 (5) | 0.0033 (5) |
C6 | 0.0218 (6) | 0.0139 (6) | 0.0193 (6) | 0.0004 (5) | −0.0032 (5) | 0.0014 (5) |
C7 | 0.0169 (6) | 0.0175 (6) | 0.0170 (6) | −0.0023 (5) | −0.0007 (5) | −0.0011 (5) |
C8 | 0.0206 (6) | 0.0185 (6) | 0.0192 (6) | −0.0024 (5) | 0.0018 (5) | −0.0018 (5) |
Geometric parameters (Å, º) top
F1—C8 | 1.3365 (15) | C2—H2 | 0.931 (15) |
F2—C8 | 1.3444 (14) | C3—C4 | 1.3943 (17) |
F3—C8 | 1.3387 (15) | C3—C6 | 1.4999 (17) |
O1—C7 | 1.4118 (15) | C4—C5 | 1.3706 (18) |
O1—C6 | 1.4210 (15) | C4—H4 | 0.929 (16) |
N1—C5 | 1.3403 (17) | C5—H5 | 0.942 (16) |
N1—C1 | 1.3403 (17) | C6—H6A | 0.980 (15) |
N1—H1A | 0.906 (18) | C6—H6B | 0.961 (16) |
C1—C2 | 1.3752 (18) | C7—C8 | 1.4933 (18) |
C1—H1 | 0.931 (15) | C7—H7A | 0.944 (15) |
C2—C3 | 1.3932 (17) | C7—H7B | 0.975 (15) |
| | | |
C7—O1—C6 | 112.05 (9) | O1—C6—C3 | 107.21 (10) |
C5—N1—C1 | 122.03 (11) | O1—C6—H6A | 110.2 (9) |
C5—N1—H1A | 117.9 (11) | C3—C6—H6A | 110.1 (9) |
C1—N1—H1A | 120.1 (11) | O1—C6—H6B | 110.1 (9) |
N1—C1—C2 | 119.86 (12) | C3—C6—H6B | 110.4 (9) |
N1—C1—H1 | 117.9 (9) | H6A—C6—H6B | 108.9 (12) |
C2—C1—H1 | 122.3 (9) | O1—C7—C8 | 106.41 (10) |
C1—C2—C3 | 119.77 (12) | O1—C7—H7A | 112.4 (9) |
C1—C2—H2 | 118.7 (9) | C8—C7—H7A | 106.6 (9) |
C3—C2—H2 | 121.5 (9) | O1—C7—H7B | 111.7 (8) |
C2—C3—C4 | 118.46 (12) | C8—C7—H7B | 107.4 (9) |
C2—C3—C6 | 120.99 (11) | H7A—C7—H7B | 111.9 (12) |
C4—C3—C6 | 120.54 (11) | F1—C8—F3 | 106.94 (11) |
C5—C4—C3 | 119.63 (12) | F1—C8—F2 | 106.63 (10) |
C5—C4—H4 | 118.2 (9) | F3—C8—F2 | 106.73 (10) |
C3—C4—H4 | 122.1 (9) | F1—C8—C7 | 112.83 (11) |
N1—C5—C4 | 120.20 (12) | F3—C8—C7 | 112.90 (11) |
N1—C5—H5 | 117.0 (9) | F2—C8—C7 | 110.42 (10) |
C4—C5—H5 | 122.8 (9) | | |
| | | |
C5—N1—C1—C2 | −0.68 (18) | C7—O1—C6—C3 | 178.44 (10) |
N1—C1—C2—C3 | −1.10 (19) | C2—C3—C6—O1 | 149.91 (11) |
C1—C2—C3—C4 | 2.32 (18) | C4—C3—C6—O1 | −31.00 (16) |
C1—C2—C3—C6 | −178.58 (12) | C6—O1—C7—C8 | 175.04 (10) |
C2—C3—C4—C5 | −1.84 (18) | O1—C7—C8—F1 | −58.56 (14) |
C6—C3—C4—C5 | 179.06 (11) | O1—C7—C8—F3 | 62.84 (13) |
C1—N1—C5—C4 | 1.17 (19) | O1—C7—C8—F2 | −177.77 (10) |
C3—C4—C5—N1 | 0.13 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl1 | 0.91 (2) | 2.09 (2) | 2.979 (1) | 167 (2) |
C1—H1···Cl1i | 0.93 (2) | 2.74 (2) | 3.411 (1) | 130 (1) |
C5—H5···Cl1ii | 0.94 (2) | 2.72 (2) | 3.451 (1) | 135 (1) |
C6—H6A···Cl1iii | 0.98 (2) | 2.95 (2) | 3.782 (1) | 144 (1) |
C7—H7A···Cl1iv | 0.94 (2) | 2.74 (1) | 3.585 (1) | 150 (1) |
C7—H7B···Cl1iii | 0.98 (1) | 2.73 (1) | 3.585 (1) | 150 (1) |
C5—H5···F1v | 0.94 (2) | 2.65 (2) | 3.190 (2) | 117 (1) |
C8—F2···C3vi | 1.34 (1) | 3.12 (1) | | 118 (1) |
Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) −x, −y, −z; (iii) −x+1/2, −y, z+1/2; (iv) −x+1, −y, −z; (v) x−1/2, −y+1/2, −z; (vi) −x+1, y+1/2, −z+1/2. |