Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029769/ac6135sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029769/ac6135Isup2.hkl |
CCDC reference: 259603
Data collection: PROTEUM (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
C23H26P+·Br− | F(000) = 856 |
Mr = 413.32 | Dx = 1.365 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 20273 reflections |
a = 11.6338 (4) Å | θ = 3.9–68.2° |
b = 10.3522 (3) Å | µ = 3.53 mm−1 |
c = 17.2434 (5) Å | T = 102 K |
β = 104.393 (2)° | Prism, colorless |
V = 2011.54 (11) Å3 | 0.28 × 0.18 × 0.15 mm |
Z = 4 |
Bruker CCD plate diffractometer | 3684 independent reflections |
Radiation source: rotating anode | 2694 reflections with I > 2σ(I) |
Göbel focusing mirrors monochromator | Rint = 0.098 |
Detector resolution: 17 pixels mm-1 | θmax = 68.4°, θmin = 3.9° |
ω scans | h = −14→13 |
Absorption correction: multi-scan (Blessing, 1995) | k = −8→12 |
Tmin = 0.36, Tmax = 0.59 | l = −20→20 |
19502 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.0453P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.089 | (Δ/σ)max = 0.001 |
S = 0.94 | Δρmax = 0.71 e Å−3 |
3684 reflections | Δρmin = −0.43 e Å−3 |
226 parameters |
Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections. |
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 | ||
C11 | 0.3351 (2) | 0.5722 (3) | 0.50799 (16) | 0.0226 (7) | |
H11A | 0.3418 | 0.5083 | 0.4667 | 0.027* | |
H11B | 0.4155 | 0.6065 | 0.532 | 0.027* | |
C12 | 0.2886 (3) | 0.5041 (3) | 0.57335 (16) | 0.0270 (7) | |
H12A | 0.2915 | 0.565 | 0.6181 | 0.032* | |
H12B | 0.2047 | 0.4791 | 0.5511 | 0.032* | |
C13 | 0.3612 (3) | 0.3834 (3) | 0.60545 (16) | 0.0283 (7) | |
H13A | 0.4462 | 0.4075 | 0.6215 | 0.034* | |
H13B | 0.3384 | 0.3538 | 0.6541 | 0.034* | |
C14 | 0.3462 (3) | 0.2705 (3) | 0.54635 (17) | 0.0277 (7) | |
H14A | 0.3676 | 0.2997 | 0.4971 | 0.033* | |
H14B | 0.4015 | 0.2004 | 0.5703 | 0.033* | |
C15 | 0.2213 (3) | 0.2181 (3) | 0.5243 (2) | 0.0429 (9) | |
H15A | 0.2163 | 0.1466 | 0.4864 | 0.064* | |
H15B | 0.1662 | 0.2867 | 0.4997 | 0.064* | |
H15C | 0.2003 | 0.1869 | 0.5727 | 0.064* | |
C21 | 0.3150 (2) | 0.8034 (3) | 0.40273 (16) | 0.0228 (7) | |
C22 | 0.3478 (2) | 0.7465 (3) | 0.33840 (15) | 0.0256 (7) | |
H22 | 0.3338 | 0.6573 | 0.3272 | 0.031* | |
C23 | 0.4012 (3) | 0.8218 (4) | 0.29077 (17) | 0.0324 (8) | |
H23 | 0.4255 | 0.7834 | 0.2474 | 0.039* | |
C24 | 0.4192 (3) | 0.9522 (4) | 0.30585 (18) | 0.0339 (8) | |
H24 | 0.4548 | 1.0031 | 0.2723 | 0.041* | |
C25 | 0.3858 (3) | 1.0093 (3) | 0.36970 (19) | 0.0342 (8) | |
H25 | 0.3982 | 1.099 | 0.3801 | 0.041* | |
C26 | 0.3338 (3) | 0.9335 (3) | 0.41808 (18) | 0.0291 (7) | |
H26 | 0.3111 | 0.9716 | 0.4622 | 0.035* | |
C31 | 0.1081 (2) | 0.6423 (3) | 0.39306 (15) | 0.0227 (7) | |
C32 | 0.0899 (3) | 0.5108 (3) | 0.37978 (16) | 0.0284 (8) | |
H32 | 0.1474 | 0.4506 | 0.4072 | 0.034* | |
C33 | −0.0130 (3) | 0.4673 (3) | 0.32614 (18) | 0.0367 (8) | |
H33 | −0.0261 | 0.3773 | 0.3175 | 0.044* | |
C34 | −0.0960 (3) | 0.5548 (4) | 0.28550 (18) | 0.0391 (9) | |
H34 | −0.1664 | 0.5244 | 0.2495 | 0.047* | |
C35 | −0.0775 (3) | 0.6868 (4) | 0.29674 (18) | 0.0361 (8) | |
H35 | −0.1343 | 0.7467 | 0.2681 | 0.043* | |
C36 | 0.0248 (3) | 0.7302 (3) | 0.35034 (16) | 0.0313 (8) | |
H36 | 0.0384 | 0.8203 | 0.3581 | 0.038* | |
C41 | 0.2044 (3) | 0.7990 (3) | 0.53843 (15) | 0.0225 (7) | |
C42 | 0.2969 (3) | 0.8541 (3) | 0.59673 (17) | 0.0306 (8) | |
H42 | 0.3768 | 0.8415 | 0.5943 | 0.037* | |
C43 | 0.2724 (3) | 0.9264 (3) | 0.65746 (17) | 0.0312 (8) | |
H43 | 0.3355 | 0.9656 | 0.696 | 0.037* | |
C44 | 0.1569 (3) | 0.9427 (3) | 0.66294 (17) | 0.0319 (8) | |
H44 | 0.1407 | 0.9918 | 0.7056 | 0.038* | |
C45 | 0.0652 (3) | 0.8876 (3) | 0.60633 (18) | 0.0353 (8) | |
H45 | −0.0143 | 0.8984 | 0.6102 | 0.042* | |
C46 | 0.0885 (3) | 0.8161 (3) | 0.54344 (17) | 0.0327 (8) | |
H46 | 0.025 | 0.7793 | 0.5041 | 0.039* | |
Br | 0.62952 (3) | 0.63696 (3) | 0.668080 (17) | 0.02736 (12) | |
P | 0.24074 (7) | 0.70306 (8) | 0.46085 (4) | 0.02103 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0186 (16) | 0.0215 (18) | 0.0268 (15) | 0.0039 (14) | 0.0036 (12) | 0.0012 (13) |
C12 | 0.0302 (18) | 0.024 (2) | 0.0268 (15) | 0.0025 (15) | 0.0076 (13) | −0.0001 (13) |
C13 | 0.0314 (18) | 0.025 (2) | 0.0268 (16) | 0.0012 (15) | 0.0044 (13) | 0.0026 (13) |
C14 | 0.0259 (17) | 0.023 (2) | 0.0329 (16) | 0.0044 (15) | 0.0052 (13) | 0.0041 (14) |
C15 | 0.033 (2) | 0.025 (2) | 0.066 (2) | 0.0010 (17) | 0.0035 (17) | 0.0001 (17) |
C21 | 0.0181 (16) | 0.0221 (19) | 0.0263 (15) | −0.0036 (14) | 0.0019 (12) | 0.0029 (13) |
C22 | 0.0222 (17) | 0.0230 (19) | 0.0301 (16) | −0.0017 (14) | 0.0039 (13) | 0.0003 (13) |
C23 | 0.0263 (18) | 0.045 (2) | 0.0267 (16) | −0.0009 (16) | 0.0076 (13) | 0.0059 (15) |
C24 | 0.0212 (17) | 0.042 (2) | 0.0355 (17) | −0.0032 (16) | 0.0010 (14) | 0.0170 (17) |
C25 | 0.032 (2) | 0.018 (2) | 0.0485 (19) | −0.0027 (15) | 0.0028 (15) | 0.0066 (15) |
C26 | 0.0291 (18) | 0.022 (2) | 0.0369 (17) | 0.0004 (15) | 0.0088 (14) | 0.0005 (14) |
C31 | 0.0218 (16) | 0.0258 (19) | 0.0216 (14) | −0.0013 (14) | 0.0078 (12) | −0.0005 (13) |
C32 | 0.0320 (19) | 0.025 (2) | 0.0271 (15) | −0.0035 (15) | 0.0055 (13) | 0.0003 (14) |
C33 | 0.042 (2) | 0.031 (2) | 0.0373 (18) | −0.0183 (18) | 0.0096 (16) | −0.0090 (16) |
C34 | 0.0274 (19) | 0.058 (3) | 0.0311 (17) | −0.0137 (19) | 0.0063 (14) | −0.0080 (17) |
C35 | 0.0212 (18) | 0.049 (3) | 0.0350 (17) | 0.0055 (17) | 0.0015 (14) | 0.0049 (16) |
C36 | 0.0296 (19) | 0.031 (2) | 0.0323 (16) | 0.0013 (16) | 0.0065 (14) | −0.0001 (15) |
C41 | 0.0230 (17) | 0.0199 (18) | 0.0254 (15) | 0.0025 (14) | 0.0073 (12) | −0.0011 (13) |
C42 | 0.0272 (18) | 0.030 (2) | 0.0330 (16) | 0.0017 (16) | 0.0052 (13) | −0.0040 (15) |
C43 | 0.0330 (19) | 0.029 (2) | 0.0286 (16) | −0.0025 (16) | 0.0026 (13) | −0.0073 (14) |
C44 | 0.040 (2) | 0.028 (2) | 0.0291 (16) | 0.0046 (16) | 0.0108 (15) | −0.0031 (14) |
C45 | 0.0286 (19) | 0.040 (2) | 0.0403 (19) | 0.0059 (17) | 0.0135 (15) | −0.0062 (16) |
C46 | 0.0272 (18) | 0.035 (2) | 0.0339 (17) | −0.0036 (16) | 0.0038 (14) | −0.0079 (15) |
Br | 0.0332 (2) | 0.0206 (2) | 0.02844 (18) | 0.00006 (15) | 0.00786 (13) | 0.00176 (13) |
P | 0.0195 (4) | 0.0179 (5) | 0.0252 (4) | 0.0002 (3) | 0.0047 (3) | −0.0010 (3) |
C11—C12 | 1.537 (4) | C25—H25 | 0.95 |
C11—P | 1.804 (3) | C26—H26 | 0.95 |
C11—H11A | 0.99 | C31—C32 | 1.388 (4) |
C11—H11B | 0.99 | C31—C36 | 1.397 (4) |
C12—C13 | 1.533 (4) | C31—P | 1.802 (3) |
C12—H12A | 0.99 | C32—C33 | 1.392 (4) |
C12—H12B | 0.99 | C32—H32 | 0.95 |
C13—C14 | 1.532 (4) | C33—C34 | 1.381 (5) |
C13—H13A | 0.99 | C33—H33 | 0.95 |
C13—H13B | 0.99 | C34—C35 | 1.390 (5) |
C14—C15 | 1.508 (4) | C34—H34 | 0.95 |
C14—H14A | 0.99 | C35—C36 | 1.388 (4) |
C14—H14B | 0.99 | C35—H35 | 0.95 |
C15—H15A | 0.98 | C36—H36 | 0.95 |
C15—H15B | 0.98 | C41—C46 | 1.384 (4) |
C15—H15C | 0.98 | C41—C42 | 1.399 (4) |
C21—C26 | 1.380 (4) | C41—P | 1.799 (3) |
C21—C22 | 1.390 (4) | C42—C43 | 1.374 (4) |
C21—P | 1.805 (3) | C42—H42 | 0.95 |
C22—C23 | 1.386 (4) | C43—C44 | 1.381 (4) |
C22—H22 | 0.95 | C43—H43 | 0.95 |
C23—C24 | 1.381 (5) | C44—C45 | 1.378 (4) |
C23—H23 | 0.95 | C44—H44 | 0.95 |
C24—C25 | 1.388 (5) | C45—C46 | 1.394 (4) |
C24—H24 | 0.95 | C45—H45 | 0.95 |
C25—C26 | 1.388 (4) | C46—H46 | 0.95 |
C12—C11—P | 112.9 (2) | C21—C26—C25 | 120.6 (3) |
C12—C11—H11A | 109 | C21—C26—H26 | 119.7 |
P—C11—H11A | 109 | C25—C26—H26 | 119.7 |
C12—C11—H11B | 109 | C32—C31—C36 | 119.6 (3) |
P—C11—H11B | 109 | C32—C31—P | 121.3 (2) |
H11A—C11—H11B | 107.8 | C36—C31—P | 119.0 (2) |
C13—C12—C11 | 112.1 (2) | C31—C32—C33 | 119.8 (3) |
C13—C12—H12A | 109.2 | C31—C32—H32 | 120.1 |
C11—C12—H12A | 109.2 | C33—C32—H32 | 120.1 |
C13—C12—H12B | 109.2 | C34—C33—C32 | 120.1 (3) |
C11—C12—H12B | 109.2 | C34—C33—H33 | 119.9 |
H12A—C12—H12B | 107.9 | C32—C33—H33 | 119.9 |
C14—C13—C12 | 114.8 (2) | C33—C34—C35 | 120.7 (3) |
C14—C13—H13A | 108.6 | C33—C34—H34 | 119.7 |
C12—C13—H13A | 108.6 | C35—C34—H34 | 119.7 |
C14—C13—H13B | 108.6 | C36—C35—C34 | 119.2 (3) |
C12—C13—H13B | 108.6 | C36—C35—H35 | 120.4 |
H13A—C13—H13B | 107.5 | C34—C35—H35 | 120.4 |
C15—C14—C13 | 112.7 (3) | C35—C36—C31 | 120.5 (3) |
C15—C14—H14A | 109.1 | C35—C36—H36 | 119.7 |
C13—C14—H14A | 109.1 | C31—C36—H36 | 119.7 |
C15—C14—H14B | 109.1 | C46—C41—C42 | 119.4 (3) |
C13—C14—H14B | 109.1 | C46—C41—P | 122.0 (2) |
H14A—C14—H14B | 107.8 | C42—C41—P | 118.6 (2) |
C14—C15—H15A | 109.5 | C43—C42—C41 | 120.1 (3) |
C14—C15—H15B | 109.5 | C43—C42—H42 | 119.9 |
H15A—C15—H15B | 109.5 | C41—C42—H42 | 119.9 |
C14—C15—H15C | 109.5 | C42—C43—C44 | 120.6 (3) |
H15A—C15—H15C | 109.5 | C42—C43—H43 | 119.7 |
H15B—C15—H15C | 109.5 | C44—C43—H43 | 119.7 |
C26—C21—C22 | 120.3 (3) | C45—C44—C43 | 119.8 (3) |
C26—C21—P | 122.0 (2) | C45—C44—H44 | 120.1 |
C22—C21—P | 117.6 (2) | C43—C44—H44 | 120.1 |
C23—C22—C21 | 119.2 (3) | C44—C45—C46 | 120.3 (3) |
C23—C22—H22 | 120.4 | C44—C45—H45 | 119.9 |
C21—C22—H22 | 120.4 | C46—C45—H45 | 119.9 |
C24—C23—C22 | 120.5 (3) | C41—C46—C45 | 119.9 (3) |
C24—C23—H23 | 119.8 | C41—C46—H46 | 120.1 |
C22—C23—H23 | 119.8 | C45—C46—H46 | 120.1 |
C23—C24—C25 | 120.4 (3) | C41—P—C31 | 110.68 (13) |
C23—C24—H24 | 119.8 | C41—P—C11 | 107.97 (13) |
C25—C24—H24 | 119.8 | C31—P—C11 | 110.93 (14) |
C24—C25—C26 | 119.0 (3) | C41—P—C21 | 109.18 (14) |
C24—C25—H25 | 120.5 | C31—P—C21 | 106.95 (13) |
C26—C25—H25 | 120.5 | C11—P—C21 | 111.14 (14) |
P—C11—C12—C13 | 173.0 (2) | C42—C41—C46—C45 | −0.1 (5) |
C11—C12—C13—C14 | −69.6 (3) | P—C41—C46—C45 | 177.7 (3) |
C12—C13—C14—C15 | −63.8 (3) | C44—C45—C46—C41 | 0.9 (5) |
C26—C21—C22—C23 | 1.0 (4) | C46—C41—P—C31 | 2.1 (3) |
P—C21—C22—C23 | 177.7 (2) | C42—C41—P—C31 | 179.9 (2) |
C21—C22—C23—C24 | −1.4 (4) | C46—C41—P—C11 | −119.5 (3) |
C22—C23—C24—C25 | 1.0 (5) | C42—C41—P—C11 | 58.3 (3) |
C23—C24—C25—C26 | 0.0 (5) | C46—C41—P—C21 | 119.5 (3) |
C22—C21—C26—C25 | 0.0 (4) | C42—C41—P—C21 | −62.6 (3) |
P—C21—C26—C25 | −176.7 (2) | C32—C31—P—C41 | −122.2 (2) |
C24—C25—C26—C21 | −0.4 (5) | C36—C31—P—C41 | 60.8 (3) |
C36—C31—C32—C33 | −2.2 (4) | C32—C31—P—C11 | −2.4 (3) |
P—C31—C32—C33 | −179.1 (2) | C36—C31—P—C11 | −179.3 (2) |
C31—C32—C33—C34 | 0.8 (4) | C32—C31—P—C21 | 118.9 (2) |
C32—C33—C34—C35 | 0.8 (5) | C36—C31—P—C21 | −58.0 (3) |
C33—C34—C35—C36 | −0.9 (5) | C12—C11—P—C41 | 46.6 (2) |
C34—C35—C36—C31 | −0.5 (4) | C12—C11—P—C31 | −74.9 (2) |
C32—C31—C36—C35 | 2.1 (4) | C12—C11—P—C21 | 166.3 (2) |
P—C31—C36—C35 | 179.0 (2) | C26—C21—P—C41 | −1.8 (3) |
C46—C41—C42—C43 | −1.2 (5) | C22—C21—P—C41 | −178.6 (2) |
P—C41—C42—C43 | −179.1 (2) | C26—C21—P—C31 | 118.0 (2) |
C41—C42—C43—C44 | 1.7 (5) | C22—C21—P—C31 | −58.8 (3) |
C42—C43—C44—C45 | −1.0 (5) | C26—C21—P—C11 | −120.8 (3) |
C43—C44—C45—C46 | −0.3 (5) | C22—C21—P—C11 | 62.5 (3) |