Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052932/hb2582sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052932/hb2582Isup2.hkl |
CCDC reference: 672803
Key indicators
- Single-crystal X-ray study
- T = 133 K
- Mean (C-C) = 0.003 Å Some non-H atoms missing
- R factor = 0.032
- wR factor = 0.083
- Data-to-parameter ratio = 26.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.90 PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A .. CL3 .. 2.93 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H14 .. CL1 .. 2.87 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H13 .. BR1 .. 2.99 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C H Cl3
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C34 H36 Br2 Cl6 D2 P2 Atom count from the _atom_site data: C34 H38 Br2 Cl6 P2 ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.897 Tmax scaled 0.450 Tmin scaled 0.323 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: Large difference may be due to a symmetry error - see SYMMG tests From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C34 H36 Br2 Cl6 D2 P2 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 136.00 136.00 0.00 H 144.00 152.00 -8.00 Br 8.00 8.00 0.00 Cl 24.00 24.00 0.00 D 8.00 0.00 8.00 P 8.00 8.00 0.00
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Brown & Trefonas (1972); Duraczynska & Nelson (2005); Hinton & Mann (1959); Matt et al. (1996).
The title compound was been prepared from the corresponding diphosphine, (PhCH2)2PCH2CH2P(CH2Ph)2, and 1,2-dibromoethane according to the procedure given by Hinton & Mann (1959). Colourless blocks of (I) were obtained from deuterated chloroform by slow evaporation at room temperature.
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C32H36P22+·2Br−·2CDCl3 | F(000) = 1776 |
Mr = 883.08 | Dx = 1.595 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 8675 reflections |
a = 16.2692 (10) Å | θ = 2.3–30.4° |
b = 17.5649 (10) Å | µ = 2.75 mm−1 |
c = 13.9110 (8) Å | T = 133 K |
β = 112.350 (3)° | Block, colourless |
V = 3676.7 (4) Å3 | 0.38 × 0.30 × 0.29 mm |
Z = 4 |
Bruker SMART1000 CCD diffractometer | 5373 independent reflections |
Radiation source: fine-focus sealed tube | 4684 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 8.192 pixels mm-1 | θmax = 30.0°, θmin = 1.8° |
ω scans | h = −22→22 |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | k = −24→24 |
Tmin = 0.360, Tmax = 0.502 | l = −19→19 |
37985 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0419P)2 + 6.1465P] where P = (Fo2 + 2Fc2)/3 |
5373 reflections | (Δ/σ)max < 0.001 |
200 parameters | Δρmax = 1.52 e Å−3 |
0 restraints | Δρmin = −1.05 e Å−3 |
C32H36P22+·2Br−·2CDCl3 | V = 3676.7 (4) Å3 |
Mr = 883.08 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 16.2692 (10) Å | µ = 2.75 mm−1 |
b = 17.5649 (10) Å | T = 133 K |
c = 13.9110 (8) Å | 0.38 × 0.30 × 0.29 mm |
β = 112.350 (3)° |
Bruker SMART1000 CCD diffractometer | 5373 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 4684 reflections with I > 2σ(I) |
Tmin = 0.360, Tmax = 0.502 | Rint = 0.025 |
37985 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.05 | Δρmax = 1.52 e Å−3 |
5373 reflections | Δρmin = −1.05 e Å−3 |
200 parameters |
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 > σ(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 | ||
Br1 | 0.0000 | 0.121056 (14) | 0.7500 | 0.02374 (7) | |
Br2 | 0.0000 | 0.209800 (15) | 0.2500 | 0.03136 (8) | |
P1 | 0.08262 (3) | 0.06365 (2) | 0.06148 (3) | 0.01914 (9) | |
C1 | 0.12293 (12) | 0.15385 (10) | 0.03500 (15) | 0.0246 (3) | |
H1A | 0.0881 | 0.1678 | −0.0382 | 0.030* | |
H1B | 0.1117 | 0.1932 | 0.0795 | 0.030* | |
C11 | 0.22023 (12) | 0.15556 (10) | 0.05260 (14) | 0.0238 (3) | |
C12 | 0.27929 (14) | 0.19798 (11) | 0.13390 (16) | 0.0291 (4) | |
H12 | 0.2580 | 0.2269 | 0.1773 | 0.035* | |
C13 | 0.36960 (15) | 0.19821 (13) | 0.15203 (19) | 0.0380 (5) | |
H13 | 0.4098 | 0.2274 | 0.2076 | 0.046* | |
C14 | 0.40056 (16) | 0.15622 (14) | 0.0894 (2) | 0.0421 (5) | |
H14 | 0.4624 | 0.1551 | 0.1032 | 0.050* | |
C15 | 0.34194 (17) | 0.11551 (13) | 0.0062 (2) | 0.0401 (5) | |
H15 | 0.3633 | 0.0875 | −0.0379 | 0.048* | |
C16 | 0.25188 (15) | 0.11585 (12) | −0.01245 (17) | 0.0316 (4) | |
H16 | 0.2116 | 0.0887 | −0.0702 | 0.038* | |
C2 | 0.13706 (12) | 0.03240 (10) | 0.19539 (14) | 0.0223 (3) | |
H2A | 0.1500 | 0.0777 | 0.2411 | 0.027* | |
H2B | 0.0952 | −0.0001 | 0.2132 | 0.027* | |
C21 | 0.22303 (11) | −0.01158 (10) | 0.21883 (13) | 0.0217 (3) | |
C22 | 0.30491 (13) | 0.02553 (12) | 0.25009 (15) | 0.0279 (4) | |
H22 | 0.3076 | 0.0793 | 0.2580 | 0.033* | |
C23 | 0.38249 (13) | −0.01563 (13) | 0.26965 (17) | 0.0331 (4) | |
H23 | 0.4379 | 0.0101 | 0.2912 | 0.040* | |
C24 | 0.37956 (13) | −0.09415 (13) | 0.25799 (16) | 0.0323 (4) | |
H24 | 0.4327 | −0.1220 | 0.2704 | 0.039* | |
C25 | 0.29897 (14) | −0.13164 (12) | 0.22824 (16) | 0.0293 (4) | |
H25 | 0.2968 | −0.1854 | 0.2204 | 0.035* | |
C26 | 0.22100 (12) | −0.09085 (11) | 0.20968 (14) | 0.0247 (3) | |
H26 | 0.1660 | −0.1171 | 0.1907 | 0.030* | |
C3 | −0.03415 (11) | 0.07968 (10) | 0.03025 (14) | 0.0222 (3) | |
H3A | −0.0403 | 0.1155 | 0.0821 | 0.027* | |
H3B | −0.0593 | 0.1050 | −0.0384 | 0.027* | |
C4 | −0.09037 (11) | 0.00863 (10) | 0.02692 (14) | 0.0214 (3) | |
H4A | −0.1533 | 0.0240 | 0.0059 | 0.026* | |
H4B | −0.0708 | −0.0133 | 0.0977 | 0.026* | |
Cl1 | −0.10604 (4) | 0.26705 (3) | −0.07399 (5) | 0.03723 (12) | |
Cl2 | −0.09062 (6) | 0.41535 (4) | 0.01860 (5) | 0.05499 (18) | |
Cl3 | −0.26168 (4) | 0.33812 (4) | −0.06513 (5) | 0.04406 (15) | |
C99 | −0.14538 (14) | 0.32753 (12) | 0.00011 (16) | 0.0311 (4) | |
H99 | −0.1329 | 0.3035 | 0.0694 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.02504 (12) | 0.02263 (12) | 0.02072 (12) | 0.000 | 0.00553 (9) | 0.000 |
Br2 | 0.04348 (16) | 0.02395 (13) | 0.02526 (14) | 0.000 | 0.01151 (11) | 0.000 |
P1 | 0.01808 (19) | 0.01810 (19) | 0.0191 (2) | −0.00022 (15) | 0.00459 (15) | −0.00208 (14) |
C1 | 0.0265 (8) | 0.0204 (8) | 0.0244 (9) | −0.0010 (6) | 0.0069 (7) | 0.0010 (6) |
C11 | 0.0285 (8) | 0.0206 (8) | 0.0227 (8) | −0.0028 (6) | 0.0101 (7) | 0.0015 (6) |
C12 | 0.0354 (10) | 0.0241 (8) | 0.0280 (10) | −0.0065 (7) | 0.0121 (8) | −0.0021 (7) |
C13 | 0.0337 (10) | 0.0371 (11) | 0.0396 (12) | −0.0147 (9) | 0.0099 (9) | 0.0022 (9) |
C14 | 0.0327 (11) | 0.0446 (13) | 0.0539 (15) | −0.0049 (9) | 0.0220 (10) | 0.0125 (11) |
C15 | 0.0479 (13) | 0.0375 (11) | 0.0479 (14) | −0.0006 (10) | 0.0329 (11) | 0.0038 (10) |
C16 | 0.0393 (11) | 0.0315 (10) | 0.0281 (10) | −0.0047 (8) | 0.0174 (8) | −0.0017 (7) |
C2 | 0.0225 (8) | 0.0241 (8) | 0.0193 (8) | 0.0018 (6) | 0.0069 (6) | −0.0002 (6) |
C21 | 0.0218 (8) | 0.0252 (8) | 0.0176 (8) | 0.0008 (6) | 0.0067 (6) | 0.0024 (6) |
C22 | 0.0262 (9) | 0.0288 (9) | 0.0260 (9) | −0.0028 (7) | 0.0069 (7) | 0.0036 (7) |
C23 | 0.0228 (9) | 0.0431 (11) | 0.0335 (11) | −0.0030 (8) | 0.0107 (8) | 0.0043 (9) |
C24 | 0.0273 (9) | 0.0427 (11) | 0.0294 (10) | 0.0093 (8) | 0.0138 (8) | 0.0051 (8) |
C25 | 0.0331 (10) | 0.0286 (9) | 0.0261 (9) | 0.0054 (8) | 0.0113 (7) | 0.0024 (7) |
C26 | 0.0238 (8) | 0.0261 (8) | 0.0225 (8) | −0.0006 (7) | 0.0067 (6) | 0.0009 (6) |
C3 | 0.0202 (7) | 0.0193 (8) | 0.0243 (8) | 0.0026 (6) | 0.0053 (6) | −0.0025 (6) |
C4 | 0.0213 (8) | 0.0214 (8) | 0.0208 (8) | 0.0012 (6) | 0.0070 (6) | −0.0020 (6) |
Cl1 | 0.0334 (2) | 0.0369 (3) | 0.0452 (3) | 0.0021 (2) | 0.0192 (2) | 0.0015 (2) |
Cl2 | 0.0842 (5) | 0.0376 (3) | 0.0367 (3) | −0.0212 (3) | 0.0157 (3) | −0.0044 (2) |
Cl3 | 0.0367 (3) | 0.0499 (3) | 0.0516 (3) | 0.0161 (2) | 0.0235 (2) | 0.0209 (3) |
C99 | 0.0363 (10) | 0.0303 (10) | 0.0264 (10) | −0.0011 (8) | 0.0115 (8) | 0.0040 (7) |
P1—C3 | 1.8027 (18) | Cl2—C99 | 1.751 (2) |
P1—C4i | 1.8050 (18) | Cl3—C99 | 1.770 (2) |
P1—C1 | 1.8053 (18) | C1—H1A | 0.9900 |
P1—C2 | 1.8170 (18) | C1—H1B | 0.9900 |
C1—C11 | 1.507 (3) | C12—H12 | 0.9500 |
C11—C16 | 1.387 (3) | C13—H13 | 0.9500 |
C11—C12 | 1.389 (3) | C14—H14 | 0.9500 |
C12—C13 | 1.393 (3) | C15—H15 | 0.9500 |
C13—C14 | 1.375 (4) | C16—H16 | 0.9500 |
C14—C15 | 1.386 (4) | C2—H2A | 0.9900 |
C15—C16 | 1.387 (3) | C2—H2B | 0.9900 |
C2—C21 | 1.521 (2) | C22—H22 | 0.9500 |
C21—C22 | 1.396 (3) | C23—H23 | 0.9500 |
C21—C26 | 1.397 (3) | C24—H24 | 0.9500 |
C22—C23 | 1.389 (3) | C25—H25 | 0.9500 |
C23—C24 | 1.387 (3) | C26—H26 | 0.9500 |
C24—C25 | 1.383 (3) | C3—H3A | 0.9900 |
C25—C26 | 1.393 (3) | C3—H3B | 0.9900 |
C3—C4 | 1.538 (2) | C4—H4A | 0.9900 |
C4—P1i | 1.8049 (18) | C4—H4B | 0.9900 |
Cl1—C99 | 1.761 (2) | C99—H99 | 1.0000 |
C3—P1—C4i | 106.61 (8) | C14—C13—H13 | 120.0 |
C3—P1—C1 | 104.19 (8) | C12—C13—H13 | 120.0 |
C4i—P1—C1 | 110.70 (9) | C13—C14—H14 | 119.9 |
C3—P1—C2 | 110.63 (9) | C15—C14—H14 | 119.9 |
C4i—P1—C2 | 110.66 (8) | C14—C15—H15 | 120.1 |
C1—P1—C2 | 113.65 (8) | C16—C15—H15 | 120.1 |
C11—C1—P1 | 115.15 (13) | C11—C16—H16 | 119.7 |
C16—C11—C12 | 119.16 (19) | C15—C16—H16 | 119.7 |
C16—C11—C1 | 120.75 (17) | C21—C2—H2A | 108.5 |
C12—C11—C1 | 120.09 (17) | P1—C2—H2A | 108.5 |
C11—C12—C13 | 120.3 (2) | C21—C2—H2B | 108.5 |
C14—C13—C12 | 119.9 (2) | P1—C2—H2B | 108.5 |
C13—C14—C15 | 120.3 (2) | H2A—C2—H2B | 107.5 |
C14—C15—C16 | 119.8 (2) | C23—C22—H22 | 119.8 |
C11—C16—C15 | 120.5 (2) | C21—C22—H22 | 119.8 |
C21—C2—P1 | 115.04 (12) | C24—C23—H23 | 119.8 |
C22—C21—C26 | 118.72 (17) | C22—C23—H23 | 119.8 |
C22—C21—C2 | 121.37 (17) | C25—C24—H24 | 120.2 |
C26—C21—C2 | 119.91 (16) | C23—C24—H24 | 120.2 |
C23—C22—C21 | 120.44 (19) | C24—C25—H25 | 119.9 |
C24—C23—C22 | 120.42 (19) | C26—C25—H25 | 119.9 |
C25—C24—C23 | 119.67 (18) | C25—C26—H26 | 119.8 |
C24—C25—C26 | 120.25 (19) | C21—C26—H26 | 119.8 |
C25—C26—C21 | 120.48 (17) | C4—C3—H3A | 108.2 |
C4—C3—P1 | 116.16 (12) | P1—C3—H3A | 108.2 |
C3—C4—P1i | 113.36 (12) | C4—C3—H3B | 108.2 |
Cl2—C99—Cl1 | 109.85 (12) | P1—C3—H3B | 108.2 |
Cl2—C99—Cl3 | 111.58 (12) | H3A—C3—H3B | 107.4 |
Cl1—C99—Cl3 | 108.59 (12) | C3—C4—H4A | 108.9 |
C11—C1—H1A | 108.5 | P1i—C4—H4A | 108.9 |
P1—C1—H1A | 108.5 | C3—C4—H4B | 108.9 |
C11—C1—H1B | 108.5 | P1i—C4—H4B | 108.9 |
P1—C1—H1B | 108.5 | H4A—C4—H4B | 107.7 |
H1A—C1—H1B | 107.5 | Cl2—C99—H99 | 108.9 |
C11—C12—H12 | 119.9 | Cl1—C99—H99 | 108.9 |
C13—C12—H12 | 119.9 | Cl3—C99—H99 | 108.9 |
C3—P1—C1—C11 | −178.60 (14) | C1—P1—C2—C21 | −86.12 (15) |
C4i—P1—C1—C11 | −64.34 (16) | P1—C2—C21—C22 | 89.50 (19) |
C2—P1—C1—C11 | 60.91 (16) | P1—C2—C21—C26 | −90.81 (18) |
P1—C1—C11—C16 | 69.5 (2) | C26—C21—C22—C23 | 1.2 (3) |
P1—C1—C11—C12 | −111.24 (18) | C2—C21—C22—C23 | −179.06 (18) |
C16—C11—C12—C13 | −2.4 (3) | C21—C22—C23—C24 | 0.3 (3) |
C1—C11—C12—C13 | 178.39 (18) | C22—C23—C24—C25 | −1.0 (3) |
C11—C12—C13—C14 | −0.1 (3) | C23—C24—C25—C26 | 0.2 (3) |
C12—C13—C14—C15 | 2.1 (3) | C24—C25—C26—C21 | 1.3 (3) |
C13—C14—C15—C16 | −1.5 (4) | C22—C21—C26—C25 | −2.0 (3) |
C12—C11—C16—C15 | 3.0 (3) | C2—C21—C26—C25 | 178.29 (17) |
C1—C11—C16—C15 | −177.79 (19) | C4i—P1—C3—C4 | 52.58 (17) |
C14—C15—C16—C11 | −1.1 (3) | C1—P1—C3—C4 | 169.70 (13) |
C3—P1—C2—C21 | 157.08 (13) | C2—P1—C3—C4 | −67.81 (15) |
C4i—P1—C2—C21 | 39.15 (16) | P1—C3—C4—P1i | −56.00 (16) |
Symmetry code: (i) −x, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···Cl3ii | 0.99 | 2.93 | 3.8486 (19) | 155 |
C14—H14···Cl1iii | 0.95 | 2.87 | 3.686 (2) | 145 |
C13—H13···Br1iv | 0.95 | 2.99 | 3.773 (2) | 141 |
C2—H2B···Br1v | 0.99 | 2.79 | 3.7553 (18) | 166 |
C4—H4B···Br1v | 0.99 | 2.75 | 3.6757 (18) | 157 |
C1—H1A···Br1vi | 0.99 | 2.86 | 3.7443 (19) | 149 |
Symmetry codes: (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1/2, −y+1/2, −z; (iv) −x+1/2, −y+1/2, −z+1; (v) −x, −y, −z+1; (vi) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C32H36P22+·2Br−·2CDCl3 |
Mr | 883.08 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 133 |
a, b, c (Å) | 16.2692 (10), 17.5649 (10), 13.9110 (8) |
β (°) | 112.350 (3) |
V (Å3) | 3676.7 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.75 |
Crystal size (mm) | 0.38 × 0.30 × 0.29 |
Data collection | |
Diffractometer | Bruker SMART1000 CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.360, 0.502 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 37985, 5373, 4684 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.704 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.083, 1.05 |
No. of reflections | 5373 |
No. of parameters | 200 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.52, −1.05 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Siemens, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···Cl3ii | 0.99 | 2.93 | 3.8486 (19) | 155 |
C14—H14···Cl1iii | 0.95 | 2.87 | 3.686 (2) | 145 |
C13—H13···Br1iv | 0.95 | 2.99 | 3.773 (2) | 141 |
C2—H2B···Br1v | 0.99 | 2.79 | 3.7553 (18) | 166 |
C4—H4B···Br1v | 0.99 | 2.75 | 3.6757 (18) | 157 |
C1—H1A···Br1vi | 0.99 | 2.86 | 3.7443 (19) | 149 |
Symmetry codes: (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1/2, −y+1/2, −z; (iv) −x+1/2, −y+1/2, −z+1; (v) −x, −y, −z+1; (vi) x, y, z−1. |
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Similar to the homologue structures known in the literature (Brown & Trefonas, 1972; Matt et al., 1996; Duraczynska & Nelson, 2005) the diphosphonium ring, in the title compound, (I), which sits on a crystallographic center of symmetry, is in a chair conformation with the torsion angles of 52.58 (17)° (C4i—P—C3—C4) and -56.00 (16)° (P—C3—C4—Pi) (i: -x,-y,-z). Each phosphorus atom has two benzyl groups attached, one of which is equatorial and the other axial. The mean P—C bond distance in (I) of 1.80 (18) Å is in accordance with the reported data for other cyclic diphosphonium salts. The P atom in (I) displays a slightly distorted tetrahedral geometry with C—P—C angles ranging from 106.61 (8)° to 113.65 (8)°. The C2—P1—C1 angle is intermediate between that of phenyl (Brown & Trefonas, 1972; Matt et al., 1996) and cyclohexyl substituted derivatives (Duraczynska & Nelson, 2005). The phenyl rings are tilted to each other with an angle of 47.42 (10)°.
Unlike the phenyl analog (Matt et al., 1996), the packing for (I) is consolidated by weak C—H···Cl and C—H···Br interactions (Table 1), linking the dication, the anions, and the deuterated solvent molecule.