Acta Cryst. (2007). E63, o3951 [ doi:10.1107/S160053680704192X ]
The title compound, C19H18P+·Br-·0.5CHCl3, was obtained by recrystallization from wet chloroform/diethyl ether and was found to crystallize as the chloroform hemisolvate. There are two independent cations and anions in the asymmetric unit along with one chloroform solvent molecule. The phenyl rings adopt a propellor conformation in both independent cations, but with opposite directions of rotation.
Crystals of the title compound were obtained by recrystallization of a commercial sample from wet chloroform/diethylether at −35 °C.
All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C) for aromatic 0.98 Å, Uiso = 1.2Ueq (C) for CH and 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms.
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).
![[Figure 1]](./sj2343fig1thm.gif)
| Fig. 1. The molecular structure of (I) showing both of the independent cations and anions with 50% probability ellipsoids. For clarity, all H atoms, other than the chloroform proton, have been omitted. |
![[Figure 2]](./sj2343fig2thm.gif)
| Fig. 2. The unit cell of (I) viewed down the a axis. For clarity, all H atoms, other than the chloroform proton, have been omitted. |
| C19H18P+·Br–·0.5CHCl3 | Z = 4 |
| Mr = 416.90 | F000 = 844 |
| Triclinic, P1 | Dx = 1.488 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 11.7690 (4) Å | Cell parameters from 8506 reflections |
| b = 11.9057 (4) Å | θ = 2.6–31.6º |
| c = 15.0898 (7) Å | µ = 2.51 mm−1 |
| α = 66.769 (1)º | T = 96 K |
| β = 73.304 (2)º | Plate, colourless |
| γ = 82.380 (1)º | 0.65 × 0.37 × 0.13 mm |
| V = 1860.57 (12) Å3 |
| Bruker APEXII CCD area-detector diffractometer | 10610 independent reflections |
| Radiation source: fine-focus sealed tube | 8893 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.019 |
| T = 96 K | θmax = 31.8º |
| φ and ω scans | θmin = 1.5º |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −17→16 |
| Tmin = 0.35, Tmax = 0.722 | k = −17→17 |
| 16377 measured reflections | l = −19→20 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
| wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 0.80 | (Δ/σ)max = 0.002 |
| 10610 reflections | Δρmax = 0.56 e Å−3 |
| 417 parameters | Δρmin = −0.50 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C19H18P+·Br–·0.5CHCl3 | γ = 82.380 (1)º |
| Mr = 416.90 | V = 1860.57 (12) Å3 |
| Triclinic, P1 | Z = 4 |
| a = 11.7690 (4) Å | Mo Kα |
| b = 11.9057 (4) Å | µ = 2.51 mm−1 |
| c = 15.0898 (7) Å | T = 96 K |
| α = 66.769 (1)º | 0.65 × 0.37 × 0.13 mm |
| β = 73.304 (2)º |
| Bruker APEXII CCD area-detector diffractometer | 10610 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | 8893 reflections with I > 2σ(I) |
| Tmin = 0.35, Tmax = 0.722 | Rint = 0.019 |
| 16377 measured reflections |
| R[F2 > 2σ(F2)] = 0.028 | 417 parameters |
| wR(F2) = 0.105 | H-atom parameters constrained |
| S = 0.80 | Δρmax = 0.56 e Å−3 |
| 10610 reflections | Δρmin = −0.50 e Å−3 |
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 > 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. |
| x | y | z | Uiso*/Ueq | ||
| C2 | 0.93549 (17) | 0.95322 (18) | 0.30581 (15) | 0.0201 (4) | |
| H2 | 0.8835 | 0.8844 | 0.3504 | 0.024* | |
| Cl1 | 1.02829 (5) | 0.91593 (6) | 0.20549 (5) | 0.03299 (13) | |
| Cl2 | 1.02403 (4) | 0.97762 (5) | 0.37316 (4) | 0.02613 (11) | |
| Cl3 | 0.84695 (4) | 1.08401 (5) | 0.26217 (4) | 0.02483 (10) | |
| Br1 | 0.264156 (16) | 0.300222 (17) | 0.597334 (13) | 0.01906 (6) | |
| Br2 | 0.639404 (16) | 0.339708 (15) | 0.215697 (13) | 0.01670 (6) | |
| P1 | 0.25469 (4) | 0.25808 (4) | 0.91409 (3) | 0.01210 (9) | |
| P2 | 0.69318 (4) | 0.28499 (4) | 0.52675 (3) | 0.01364 (9) | |
| C10 | 0.34736 (16) | 0.34979 (16) | 0.79770 (13) | 0.0163 (3) | |
| H10A | 0.3415 | 0.4333 | 0.7925 | 0.024* | |
| H10B | 0.3225 | 0.3446 | 0.7442 | 0.024* | |
| H10C | 0.4281 | 0.3210 | 0.7937 | 0.024* | |
| C11 | 0.26895 (16) | 0.10230 (16) | 0.92330 (13) | 0.0150 (3) | |
| C12 | 0.38227 (19) | 0.0536 (2) | 0.8979 (2) | 0.0384 (6) | |
| H12 | 0.4484 | 0.1009 | 0.8787 | 0.046* | |
| C13 | 0.3966 (2) | −0.0660 (2) | 0.9013 (2) | 0.0377 (6) | |
| H13 | 0.4723 | −0.0985 | 0.8840 | 0.045* | |
| C14 | 0.2983 (2) | −0.13634 (17) | 0.93043 (14) | 0.0223 (4) | |
| H14 | 0.3075 | −0.2154 | 0.9310 | 0.027* | |
| C15 | 0.18653 (19) | −0.08909 (18) | 0.95866 (17) | 0.0253 (4) | |
| H15 | 0.1207 | −0.1378 | 0.9810 | 0.030* | |
| C16 | 0.17138 (17) | 0.03087 (16) | 0.95403 (15) | 0.0199 (4) | |
| H16 | 0.0955 | 0.0628 | 0.9716 | 0.024* | |
| C21 | 0.10393 (15) | 0.31162 (15) | 0.92090 (13) | 0.0150 (3) | |
| C22 | 0.05877 (17) | 0.33463 (17) | 0.83930 (15) | 0.0198 (4) | |
| H22 | 0.1056 | 0.3201 | 0.7835 | 0.024* | |
| C23 | −0.05653 (18) | 0.37937 (19) | 0.84201 (17) | 0.0259 (4) | |
| H23 | −0.0878 | 0.3937 | 0.7884 | 0.031* | |
| C24 | −0.12584 (18) | 0.40291 (18) | 0.92529 (18) | 0.0276 (5) | |
| H24 | −0.2025 | 0.4348 | 0.9261 | 0.033* | |
| C25 | −0.08197 (18) | 0.37942 (18) | 1.00572 (17) | 0.0257 (4) | |
| H25 | −0.1292 | 0.3941 | 1.0613 | 0.031* | |
| C26 | 0.03339 (17) | 0.33354 (17) | 1.00444 (15) | 0.0205 (4) | |
| H26 | 0.0633 | 0.3176 | 1.0591 | 0.025* | |
| C31 | 0.29869 (15) | 0.26401 (15) | 1.01631 (12) | 0.0132 (3) | |
| C32 | 0.26180 (17) | 0.17271 (17) | 1.11113 (14) | 0.0179 (3) | |
| H32 | 0.2158 | 0.1093 | 1.1204 | 0.022* | |
| C33 | 0.29380 (17) | 0.17690 (17) | 1.19120 (13) | 0.0190 (4) | |
| H33 | 0.2677 | 0.1175 | 1.2546 | 0.023* | |
| C34 | 0.36508 (16) | 0.27013 (17) | 1.17661 (13) | 0.0176 (3) | |
| H34 | 0.3884 | 0.2717 | 1.2300 | 0.021* | |
| C35 | 0.40145 (17) | 0.36068 (17) | 1.08285 (14) | 0.0196 (4) | |
| H35 | 0.4493 | 0.4226 | 1.0737 | 0.023* | |
| C36 | 0.36723 (16) | 0.36007 (16) | 1.00226 (13) | 0.0166 (3) | |
| H36 | 0.3895 | 0.4225 | 0.9399 | 0.020* | |
| C40 | 0.59777 (16) | 0.38815 (17) | 0.45664 (14) | 0.0176 (3) | |
| H40A | 0.6074 | 0.3748 | 0.3961 | 0.026* | |
| H40B | 0.6177 | 0.4707 | 0.4406 | 0.026* | |
| H40C | 0.5169 | 0.3744 | 0.4954 | 0.026* | |
| C41 | 0.65468 (16) | 0.13170 (16) | 0.55482 (13) | 0.0149 (3) | |
| C42 | 0.53788 (17) | 0.09560 (19) | 0.60718 (15) | 0.0215 (4) | |
| H42 | 0.4833 | 0.1491 | 0.6293 | 0.026* | |
| C43 | 0.50442 (19) | −0.02113 (19) | 0.62582 (15) | 0.0260 (4) | |
| H43 | 0.4274 | −0.0462 | 0.6615 | 0.031* | |
| C44 | 0.5846 (2) | −0.09958 (18) | 0.59181 (15) | 0.0253 (4) | |
| H44 | 0.5608 | −0.1765 | 0.6029 | 0.030* | |
| C45 | 0.7000 (2) | −0.06500 (18) | 0.54136 (14) | 0.0235 (4) | |
| H45 | 0.7540 | −0.1192 | 0.5197 | 0.028* | |
| C46 | 0.73617 (17) | 0.05074 (17) | 0.52268 (14) | 0.0184 (3) | |
| H46 | 0.8141 | 0.0738 | 0.4890 | 0.022* | |
| C51 | 0.84459 (15) | 0.31220 (16) | 0.45611 (13) | 0.0150 (3) | |
| C52 | 0.87672 (17) | 0.31023 (18) | 0.36024 (14) | 0.0193 (4) | |
| H52 | 0.8198 | 0.2997 | 0.3325 | 0.023* | |
| C53 | 0.99547 (19) | 0.3242 (2) | 0.30674 (16) | 0.0261 (4) | |
| H53 | 1.0183 | 0.3214 | 0.2433 | 0.031* | |
| C54 | 1.07978 (18) | 0.34229 (19) | 0.34737 (16) | 0.0268 (4) | |
| H54 | 1.1590 | 0.3505 | 0.3113 | 0.032* | |
| C55 | 1.04735 (18) | 0.3482 (2) | 0.44120 (17) | 0.0256 (4) | |
| H55 | 1.1041 | 0.3626 | 0.4673 | 0.031* | |
| C56 | 0.92945 (17) | 0.33249 (18) | 0.49621 (15) | 0.0209 (4) | |
| H56 | 0.9072 | 0.3355 | 0.5596 | 0.025* | |
| C61 | 0.67462 (15) | 0.30612 (17) | 0.64188 (13) | 0.0161 (3) | |
| C62 | 0.68264 (17) | 0.20571 (19) | 0.72775 (14) | 0.0208 (4) | |
| H62 | 0.6945 | 0.1276 | 0.7262 | 0.025* | |
| C63 | 0.67281 (18) | 0.2224 (2) | 0.81604 (15) | 0.0249 (4) | |
| H63 | 0.6791 | 0.1557 | 0.8734 | 0.030* | |
| C64 | 0.65364 (18) | 0.3391 (2) | 0.81809 (16) | 0.0260 (4) | |
| H64 | 0.6458 | 0.3499 | 0.8774 | 0.031* | |
| C65 | 0.64605 (18) | 0.4400 (2) | 0.73253 (16) | 0.0251 (4) | |
| H65 | 0.6335 | 0.5179 | 0.7345 | 0.030* | |
| C66 | 0.65737 (17) | 0.42387 (18) | 0.64352 (15) | 0.0205 (4) | |
| H66 | 0.6534 | 0.4910 | 0.5857 | 0.025* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C2 | 0.0161 (8) | 0.0215 (9) | 0.0230 (9) | −0.0017 (7) | −0.0031 (7) | −0.0096 (7) |
| Cl1 | 0.0220 (2) | 0.0450 (3) | 0.0414 (3) | 0.0012 (2) | −0.0020 (2) | −0.0309 (3) |
| Cl2 | 0.0238 (2) | 0.0294 (2) | 0.0297 (3) | 0.00343 (19) | −0.0133 (2) | −0.0125 (2) |
| Cl3 | 0.0243 (2) | 0.0284 (2) | 0.0240 (2) | 0.00488 (19) | −0.01051 (19) | −0.01082 (19) |
| Br1 | 0.01849 (10) | 0.02193 (10) | 0.01833 (10) | −0.00370 (7) | −0.00503 (7) | −0.00796 (7) |
| Br2 | 0.01863 (10) | 0.01593 (9) | 0.01646 (9) | −0.00120 (6) | −0.00405 (7) | −0.00711 (7) |
| P1 | 0.0116 (2) | 0.01229 (19) | 0.0129 (2) | −0.00235 (15) | −0.00212 (16) | −0.00527 (16) |
| P2 | 0.0129 (2) | 0.0168 (2) | 0.0111 (2) | 0.00001 (16) | −0.00274 (16) | −0.00542 (16) |
| C10 | 0.0173 (8) | 0.0184 (8) | 0.0130 (8) | −0.0062 (6) | −0.0015 (6) | −0.0055 (6) |
| C11 | 0.0148 (8) | 0.0149 (7) | 0.0156 (8) | −0.0013 (6) | −0.0020 (6) | −0.0073 (6) |
| C12 | 0.0162 (10) | 0.0212 (10) | 0.0640 (17) | −0.0031 (8) | 0.0115 (10) | −0.0163 (11) |
| C13 | 0.0269 (11) | 0.0217 (10) | 0.0492 (15) | 0.0034 (9) | 0.0144 (10) | −0.0158 (10) |
| C14 | 0.0362 (11) | 0.0164 (8) | 0.0169 (9) | 0.0033 (8) | −0.0081 (8) | −0.0093 (7) |
| C15 | 0.0247 (10) | 0.0163 (8) | 0.0394 (12) | −0.0022 (7) | −0.0160 (9) | −0.0091 (8) |
| C16 | 0.0155 (8) | 0.0156 (8) | 0.0305 (10) | 0.0006 (6) | −0.0074 (7) | −0.0099 (7) |
| C21 | 0.0136 (8) | 0.0122 (7) | 0.0198 (8) | −0.0014 (6) | −0.0034 (6) | −0.0069 (6) |
| C22 | 0.0181 (9) | 0.0200 (8) | 0.0216 (9) | −0.0008 (7) | −0.0061 (7) | −0.0074 (7) |
| C23 | 0.0227 (10) | 0.0221 (9) | 0.0327 (11) | 0.0010 (8) | −0.0142 (8) | −0.0056 (8) |
| C24 | 0.0146 (9) | 0.0169 (8) | 0.0520 (14) | 0.0021 (7) | −0.0094 (9) | −0.0137 (9) |
| C25 | 0.0172 (9) | 0.0214 (9) | 0.0394 (12) | −0.0030 (7) | 0.0016 (8) | −0.0177 (9) |
| C26 | 0.0172 (9) | 0.0205 (8) | 0.0259 (10) | −0.0029 (7) | −0.0017 (7) | −0.0128 (7) |
| C31 | 0.0123 (7) | 0.0149 (7) | 0.0127 (8) | −0.0014 (6) | −0.0025 (6) | −0.0056 (6) |
| C32 | 0.0189 (8) | 0.0169 (8) | 0.0160 (8) | −0.0061 (7) | −0.0019 (7) | −0.0042 (7) |
| C33 | 0.0222 (9) | 0.0200 (8) | 0.0115 (8) | −0.0027 (7) | −0.0027 (7) | −0.0028 (7) |
| C34 | 0.0198 (9) | 0.0205 (8) | 0.0144 (8) | 0.0013 (7) | −0.0058 (7) | −0.0079 (7) |
| C35 | 0.0233 (9) | 0.0192 (8) | 0.0184 (9) | −0.0063 (7) | −0.0065 (7) | −0.0066 (7) |
| C36 | 0.0201 (9) | 0.0158 (8) | 0.0129 (8) | −0.0050 (7) | −0.0030 (7) | −0.0037 (6) |
| C40 | 0.0166 (8) | 0.0207 (8) | 0.0167 (8) | 0.0036 (7) | −0.0063 (7) | −0.0082 (7) |
| C41 | 0.0149 (8) | 0.0163 (8) | 0.0139 (8) | −0.0015 (6) | −0.0056 (6) | −0.0045 (6) |
| C42 | 0.0151 (8) | 0.0249 (9) | 0.0208 (9) | −0.0030 (7) | −0.0034 (7) | −0.0049 (7) |
| C43 | 0.0250 (10) | 0.0259 (10) | 0.0221 (10) | −0.0106 (8) | −0.0094 (8) | 0.0015 (8) |
| C44 | 0.0397 (12) | 0.0203 (9) | 0.0178 (9) | −0.0097 (8) | −0.0141 (8) | −0.0016 (7) |
| C45 | 0.0370 (11) | 0.0178 (9) | 0.0150 (8) | −0.0028 (8) | −0.0064 (8) | −0.0049 (7) |
| C46 | 0.0205 (9) | 0.0182 (8) | 0.0151 (8) | −0.0016 (7) | −0.0033 (7) | −0.0053 (7) |
| C51 | 0.0133 (8) | 0.0149 (7) | 0.0153 (8) | −0.0012 (6) | −0.0030 (6) | −0.0042 (6) |
| C52 | 0.0193 (9) | 0.0212 (8) | 0.0182 (9) | −0.0032 (7) | −0.0017 (7) | −0.0095 (7) |
| C53 | 0.0224 (10) | 0.0300 (10) | 0.0225 (10) | −0.0054 (8) | 0.0048 (8) | −0.0123 (8) |
| C54 | 0.0163 (9) | 0.0265 (10) | 0.0303 (11) | −0.0037 (8) | 0.0034 (8) | −0.0086 (8) |
| C55 | 0.0173 (9) | 0.0277 (10) | 0.0309 (11) | −0.0015 (8) | −0.0096 (8) | −0.0074 (8) |
| C56 | 0.0172 (9) | 0.0254 (9) | 0.0187 (9) | −0.0007 (7) | −0.0055 (7) | −0.0062 (7) |
| C61 | 0.0120 (8) | 0.0237 (9) | 0.0138 (8) | −0.0011 (6) | −0.0026 (6) | −0.0085 (7) |
| C62 | 0.0205 (9) | 0.0260 (9) | 0.0156 (8) | 0.0034 (7) | −0.0052 (7) | −0.0084 (7) |
| C63 | 0.0214 (10) | 0.0378 (11) | 0.0159 (9) | 0.0010 (8) | −0.0063 (7) | −0.0099 (8) |
| C64 | 0.0173 (9) | 0.0457 (12) | 0.0230 (10) | −0.0022 (8) | −0.0045 (8) | −0.0212 (9) |
| C65 | 0.0204 (9) | 0.0331 (11) | 0.0290 (11) | −0.0042 (8) | −0.0032 (8) | −0.0201 (9) |
| C66 | 0.0177 (9) | 0.0236 (9) | 0.0218 (9) | −0.0033 (7) | −0.0032 (7) | −0.0104 (7) |
| C2—Cl3 | 1.761 (2) | C33—H33 | 0.9300 |
| C2—Cl2 | 1.768 (2) | C34—C35 | 1.385 (3) |
| C2—Cl1 | 1.770 (2) | C34—H34 | 0.9300 |
| C2—H2 | 0.9800 | C35—C36 | 1.389 (3) |
| P1—C10 | 1.7801 (17) | C35—H35 | 0.9300 |
| P1—C31 | 1.7908 (17) | C36—H36 | 0.9300 |
| P1—C21 | 1.7922 (18) | C40—H40A | 0.9600 |
| P1—C11 | 1.7930 (18) | C40—H40B | 0.9600 |
| P2—C40 | 1.7834 (18) | C40—H40C | 0.9600 |
| P2—C41 | 1.7930 (18) | C41—C46 | 1.393 (3) |
| P2—C51 | 1.7905 (18) | C41—C42 | 1.401 (2) |
| P2—C61 | 1.8003 (18) | C42—C43 | 1.392 (3) |
| C10—H10A | 0.9600 | C42—H42 | 0.9300 |
| C10—H10B | 0.9600 | C43—C44 | 1.376 (3) |
| C10—H10C | 0.9600 | C43—H43 | 0.9300 |
| C11—C16 | 1.378 (2) | C44—C45 | 1.379 (3) |
| C11—C12 | 1.392 (3) | C44—H44 | 0.9300 |
| C12—C13 | 1.394 (3) | C45—C46 | 1.393 (3) |
| C12—H12 | 0.9300 | C45—H45 | 0.9300 |
| C13—C14 | 1.380 (3) | C46—H46 | 0.9300 |
| C13—H13 | 0.9300 | C51—C56 | 1.396 (3) |
| C14—C15 | 1.378 (3) | C51—C52 | 1.395 (3) |
| C14—H14 | 0.9300 | C52—C53 | 1.393 (3) |
| C15—C16 | 1.392 (3) | C52—H52 | 0.9300 |
| C15—H15 | 0.9300 | C53—C54 | 1.384 (3) |
| C16—H16 | 0.9300 | C53—H53 | 0.9300 |
| C21—C26 | 1.395 (3) | C54—C55 | 1.384 (3) |
| C21—C22 | 1.395 (3) | C54—H54 | 0.9300 |
| C22—C23 | 1.386 (3) | C55—C56 | 1.391 (3) |
| C22—H22 | 0.9300 | C55—H55 | 0.9300 |
| C23—C24 | 1.397 (3) | C56—H56 | 0.9300 |
| C23—H23 | 0.9300 | C61—C62 | 1.391 (3) |
| C24—C25 | 1.368 (3) | C61—C66 | 1.399 (3) |
| C24—H24 | 0.9300 | C62—C63 | 1.394 (3) |
| C25—C26 | 1.392 (3) | C62—H62 | 0.9300 |
| C25—H25 | 0.9300 | C63—C64 | 1.389 (3) |
| C26—H26 | 0.9300 | C63—H63 | 0.9300 |
| C31—C36 | 1.400 (2) | C64—C65 | 1.390 (3) |
| C31—C32 | 1.399 (2) | C64—H64 | 0.9300 |
| C32—C33 | 1.385 (3) | C65—C66 | 1.398 (3) |
| C32—H32 | 0.9300 | C65—H65 | 0.9300 |
| C33—C34 | 1.390 (3) | C66—H66 | 0.9300 |
| Cl3—C2—Cl2 | 110.31 (11) | C35—C34—C33 | 120.22 (17) |
| Cl3—C2—Cl1 | 110.94 (11) | C35—C34—H34 | 119.9 |
| Cl2—C2—Cl1 | 109.30 (10) | C33—C34—H34 | 119.9 |
| Cl3—C2—H2 | 108.7 | C34—C35—C36 | 120.74 (17) |
| Cl2—C2—H2 | 108.7 | C34—C35—H35 | 119.6 |
| Cl1—C2—H2 | 108.7 | C36—C35—H35 | 119.6 |
| C10—P1—C31 | 111.05 (8) | C31—C36—C35 | 118.99 (16) |
| C10—P1—C21 | 109.29 (9) | C31—C36—H36 | 120.5 |
| C31—P1—C21 | 109.44 (8) | C35—C36—H36 | 120.5 |
| C10—P1—C11 | 108.76 (8) | P2—C40—H40A | 109.5 |
| C31—P1—C11 | 107.86 (8) | P2—C40—H40B | 109.5 |
| C21—P1—C11 | 110.42 (8) | H40A—C40—H40B | 109.5 |
| C40—P2—C41 | 108.51 (9) | P2—C40—H40C | 109.5 |
| C40—P2—C51 | 109.82 (8) | H40A—C40—H40C | 109.5 |
| C41—P2—C51 | 110.49 (8) | H40B—C40—H40C | 109.5 |
| C40—P2—C61 | 110.31 (9) | C46—C41—C42 | 119.97 (17) |
| C41—P2—C61 | 108.94 (8) | C46—C41—P2 | 121.72 (14) |
| C51—P2—C61 | 108.77 (8) | C42—C41—P2 | 118.26 (14) |
| P1—C10—H10A | 109.5 | C43—C42—C41 | 119.32 (19) |
| P1—C10—H10B | 109.5 | C43—C42—H42 | 120.3 |
| H10A—C10—H10B | 109.5 | C41—C42—H42 | 120.3 |
| P1—C10—H10C | 109.5 | C44—C43—C42 | 120.37 (19) |
| H10A—C10—H10C | 109.5 | C44—C43—H43 | 119.8 |
| H10B—C10—H10C | 109.5 | C42—C43—H43 | 119.8 |
| C16—C11—C12 | 119.74 (17) | C45—C44—C43 | 120.48 (19) |
| C16—C11—P1 | 121.83 (14) | C45—C44—H44 | 119.8 |
| C12—C11—P1 | 118.43 (14) | C43—C44—H44 | 119.8 |
| C13—C12—C11 | 120.0 (2) | C44—C45—C46 | 120.3 (2) |
| C13—C12—H12 | 120.0 | C44—C45—H45 | 119.9 |
| C11—C12—H12 | 120.0 | C46—C45—H45 | 119.9 |
| C14—C13—C12 | 119.9 (2) | C45—C46—C41 | 119.53 (18) |
| C14—C13—H13 | 120.0 | C45—C46—H46 | 120.2 |
| C12—C13—H13 | 120.0 | C41—C46—H46 | 120.2 |
| C15—C14—C13 | 119.85 (18) | C56—C51—C52 | 120.46 (17) |
| C15—C14—H14 | 120.1 | C56—C51—P2 | 121.14 (14) |
| C13—C14—H14 | 120.1 | C52—C51—P2 | 118.38 (14) |
| C14—C15—C16 | 120.54 (18) | C53—C52—C51 | 118.93 (18) |
| C14—C15—H15 | 119.7 | C53—C52—H52 | 120.5 |
| C16—C15—H15 | 119.7 | C51—C52—H52 | 120.5 |
| C11—C16—C15 | 119.89 (18) | C52—C53—C54 | 120.46 (19) |
| C11—C16—H16 | 120.1 | C52—C53—H53 | 119.8 |
| C15—C16—H16 | 120.1 | C54—C53—H53 | 119.8 |
| C26—C21—C22 | 120.15 (17) | C55—C54—C53 | 120.62 (19) |
| C26—C21—P1 | 121.26 (14) | C55—C54—H54 | 119.7 |
| C22—C21—P1 | 118.57 (14) | C53—C54—H54 | 119.7 |
| C23—C22—C21 | 119.42 (19) | C54—C55—C56 | 119.62 (19) |
| C23—C22—H22 | 120.3 | C54—C55—H55 | 120.2 |
| C21—C22—H22 | 120.3 | C56—C55—H55 | 120.2 |
| C24—C23—C22 | 120.0 (2) | C55—C56—C51 | 119.86 (19) |
| C24—C23—H23 | 120.0 | C55—C56—H56 | 120.1 |
| C22—C23—H23 | 120.0 | C51—C56—H56 | 120.1 |
| C25—C24—C23 | 120.59 (19) | C62—C61—C66 | 120.36 (18) |
| C25—C24—H24 | 119.7 | C62—C61—P2 | 119.75 (15) |
| C23—C24—H24 | 119.7 | C66—C61—P2 | 119.83 (14) |
| C24—C25—C26 | 120.0 (2) | C61—C62—C63 | 119.84 (19) |
| C24—C25—H25 | 120.0 | C61—C62—H62 | 120.1 |
| C26—C25—H25 | 120.0 | C63—C62—H62 | 120.1 |
| C21—C26—C25 | 119.75 (19) | C64—C63—C62 | 119.8 (2) |
| C21—C26—H26 | 120.1 | C64—C63—H63 | 120.1 |
| C25—C26—H26 | 120.1 | C62—C63—H63 | 120.1 |
| C36—C31—C32 | 120.17 (16) | C63—C64—C65 | 120.75 (19) |
| C36—C31—P1 | 120.53 (13) | C63—C64—H64 | 119.6 |
| C32—C31—P1 | 119.28 (13) | C65—C64—H64 | 119.6 |
| C33—C32—C31 | 119.97 (17) | C64—C65—C66 | 119.6 (2) |
| C33—C32—H32 | 120.0 | C64—C65—H65 | 120.2 |
| C31—C32—H32 | 120.0 | C66—C65—H65 | 120.2 |
| C34—C33—C32 | 119.85 (17) | C61—C66—C65 | 119.60 (19) |
| C34—C33—H33 | 120.1 | C61—C66—H66 | 120.2 |
| C32—C33—H33 | 120.1 | C65—C66—H66 | 120.2 |
Bowmaker, G. A., Camus, A., Skelton, B. W. & White, A. H. (1990). J. Chem. Soc. Dalton Trans. pp. 727–731.
Bruker (2005). APEX2 (Version 2.02), SAINT (Version 7.23A) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.
Butchard, J. R., Curnow, O. J., Garrett, D. J. & Maclagan, R. G. A. R. (2006). Angew. Chem. Int. Ed. 45, 7550–7553.
El Essawi, M., Wartchow, R. & Berthold, H. J. (1996). Z. Kristallogr. 211, 265–266.
Sheldrick, G. M. (2001). SHELXTL. Version 6.12. Bruker AXS Inc., Madison, Wisconsin, USA.
Wermer, J. R., Hollander, O., Huffman, J. C., Krause Bauer, J. A., Dou, D., Hsu, L.-Y., Leussing, D. L. & Shore, S. G. (1995). Inorg. Chem. 34, 3065–3071.
Crystals of the title compound (I) were grown as part of an ongoing project on halide hydrates (Butchard et al. 2006). In this case, the compound crystallized from wet chloroform/diethylether with only chloroform solvate. The stucture of (I) is shown below (Fig. 1). The asymmetric unit consists of two phosphonium cations, two bromide anions, and one chloroform solvate molecule. The unit cell is shown in Fig. 2.