Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020483/ww6273sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020483/ww6273Isup2.hkl |
CCDC reference: 251744
Key indicators
- Single-crystal X-ray study
- T = 102 K
- Mean (C-C) = 0.004 Å
- R factor = 0.039
- wR factor = 0.112
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
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 (Farrugia, 1999).
C22H24P+·Br− | F(000) = 824 |
Mr = 399.29 | Dx = 1.406 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 19309 reflections |
a = 11.3309 (3) Å | θ = 4.1–70.1° |
b = 9.8033 (2) Å | µ = 3.75 mm−1 |
c = 17.7075 (3) Å | T = 102 K |
β = 106.487 (1)° | Prism, colorless |
V = 1886.08 (7) Å3 | 0.3 × 0.2 × 0.1 mm |
Z = 4 |
Bruker AXS diffractometer | 3555 independent reflections |
Radiation source: rotating anode | 2997 reflections with I > 2σ(I) |
Göbel focusing mirrors monochromator | Rint = 0.089 |
Detector resolution: 17 pixels mm-1 | θmax = 70.3°, θmin = 4.1° |
ω scans | h = −13→11 |
Absorption correction: multi-scan (Blessing, 1995) | k = −11→11 |
Tmin = 0.37, Tmax = 0.685 | l = −21→21 |
18578 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0659P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.112 | (Δ/σ)max = 0.035 |
S = 1.13 | Δρmax = 0.67 e Å−3 |
3555 reflections | Δρmin = −0.68 e Å−3 |
217 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 | 0.3226 (2) | 0.0231 (3) | 0.50574 (14) | 0.0244 (6) | |
H11A | 0.3367 | −0.0274 | 0.4607 | 0.029* | |
H11B | 0.4038 | 0.0545 | 0.5389 | 0.029* | |
C12 | 0.2696 (2) | −0.0774 (3) | 0.55456 (15) | 0.0268 (6) | |
H12 | 0.1796 | −0.0587 | 0.5442 | 0.032* | |
C13 | 0.3319 (3) | −0.0594 (3) | 0.64243 (15) | 0.0311 (6) | |
H13A | 0.3212 | 0.0348 | 0.6577 | 0.047* | |
H13B | 0.4199 | −0.0797 | 0.6537 | 0.047* | |
H13C | 0.2946 | −0.1219 | 0.6723 | 0.047* | |
C14 | 0.2857 (3) | −0.2251 (3) | 0.52971 (17) | 0.0329 (7) | |
H14A | 0.245 | −0.2359 | 0.4733 | 0.049* | |
H14B | 0.2488 | −0.288 | 0.5596 | 0.049* | |
H14C | 0.3736 | −0.2456 | 0.5404 | 0.049* | |
C21 | 0.3164 (2) | 0.2860 (3) | 0.42381 (14) | 0.0230 (6) | |
C22 | 0.3618 (2) | 0.2355 (3) | 0.36369 (15) | 0.0280 (6) | |
H22 | 0.352 | 0.1419 | 0.3494 | 0.034* | |
C23 | 0.4215 (3) | 0.3235 (3) | 0.32487 (16) | 0.0300 (6) | |
H23 | 0.4537 | 0.2898 | 0.2844 | 0.036* | |
C24 | 0.4340 (2) | 0.4604 (3) | 0.34519 (15) | 0.0298 (6) | |
H24 | 0.4731 | 0.5205 | 0.3177 | 0.036* | |
C25 | 0.3903 (2) | 0.5103 (3) | 0.40515 (15) | 0.0314 (7) | |
H25 | 0.4011 | 0.6038 | 0.4196 | 0.038* | |
C26 | 0.3306 (2) | 0.4241 (3) | 0.44414 (15) | 0.0270 (6) | |
H26 | 0.2993 | 0.4586 | 0.4847 | 0.032* | |
C31 | 0.0959 (2) | 0.1255 (3) | 0.39074 (15) | 0.0219 (6) | |
C32 | 0.0611 (2) | −0.0097 (3) | 0.37388 (15) | 0.0280 (6) | |
H32 | 0.1082 | −0.0812 | 0.4042 | 0.034* | |
C33 | −0.0431 (2) | −0.0396 (3) | 0.31233 (16) | 0.0321 (7) | |
H33 | −0.0679 | −0.1317 | 0.301 | 0.038* | |
C34 | −0.1102 (2) | 0.0642 (3) | 0.26789 (15) | 0.0324 (7) | |
H34 | −0.1809 | 0.0431 | 0.2257 | 0.039* | |
C35 | −0.0758 (2) | 0.1995 (3) | 0.28406 (17) | 0.0330 (7) | |
H35 | −0.1228 | 0.2707 | 0.2533 | 0.04* | |
C36 | 0.0270 (2) | 0.2294 (3) | 0.34516 (16) | 0.0298 (6) | |
H36 | 0.0512 | 0.3217 | 0.3563 | 0.036* | |
C41 | 0.1883 (2) | 0.2622 (3) | 0.54405 (14) | 0.0223 (5) | |
C42 | 0.2834 (2) | 0.3073 (3) | 0.60889 (15) | 0.0265 (6) | |
H42 | 0.3664 | 0.2824 | 0.6141 | 0.032* | |
C43 | 0.2545 (3) | 0.3886 (3) | 0.66515 (16) | 0.0297 (6) | |
H43 | 0.3186 | 0.4216 | 0.7084 | 0.036* | |
C44 | 0.1341 (3) | 0.4222 (3) | 0.65936 (16) | 0.0313 (7) | |
H44 | 0.1157 | 0.4778 | 0.6984 | 0.038* | |
C45 | 0.0401 (3) | 0.3747 (3) | 0.59645 (18) | 0.0335 (7) | |
H45 | −0.043 | 0.3962 | 0.593 | 0.04* | |
C46 | 0.0673 (2) | 0.2954 (3) | 0.53823 (16) | 0.0275 (6) | |
H46 | 0.0029 | 0.2642 | 0.4946 | 0.033* | |
Br | 0.62321 (2) | 0.14750 (3) | 0.671491 (15) | 0.02752 (14) | |
P | 0.23154 (6) | 0.17055 (7) | 0.46802 (4) | 0.02026 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0264 (13) | 0.0216 (14) | 0.0251 (12) | 0.0022 (11) | 0.0071 (11) | 0.0004 (11) |
C12 | 0.0266 (13) | 0.0211 (15) | 0.0330 (14) | 0.0001 (11) | 0.0090 (11) | 0.0023 (12) |
C13 | 0.0362 (14) | 0.0265 (16) | 0.0313 (14) | −0.0022 (12) | 0.0109 (12) | 0.0012 (12) |
C14 | 0.0415 (16) | 0.0200 (16) | 0.0350 (15) | −0.0023 (12) | 0.0074 (13) | 0.0029 (12) |
C21 | 0.0236 (12) | 0.0202 (14) | 0.0242 (12) | −0.0016 (10) | 0.0049 (10) | 0.0001 (11) |
C22 | 0.0334 (14) | 0.0188 (14) | 0.0325 (14) | −0.0006 (11) | 0.0104 (12) | 0.0019 (12) |
C23 | 0.0328 (14) | 0.0302 (17) | 0.0295 (14) | 0.0020 (12) | 0.0129 (12) | 0.0043 (12) |
C24 | 0.0286 (14) | 0.0307 (17) | 0.0273 (13) | −0.0047 (12) | 0.0030 (11) | 0.0076 (13) |
C25 | 0.0347 (15) | 0.0225 (15) | 0.0321 (14) | −0.0028 (12) | 0.0017 (12) | 0.0028 (12) |
C26 | 0.0307 (14) | 0.0211 (15) | 0.0283 (13) | −0.0015 (11) | 0.0069 (11) | −0.0018 (12) |
C31 | 0.0204 (12) | 0.0223 (14) | 0.0224 (12) | −0.0034 (10) | 0.0051 (10) | −0.0029 (11) |
C32 | 0.0316 (14) | 0.0245 (16) | 0.0267 (13) | 0.0012 (11) | 0.0065 (11) | 0.0005 (12) |
C33 | 0.0328 (14) | 0.0291 (17) | 0.0334 (15) | −0.0060 (12) | 0.0079 (12) | −0.0061 (13) |
C34 | 0.0236 (13) | 0.045 (2) | 0.0266 (13) | −0.0057 (12) | 0.0036 (11) | −0.0030 (13) |
C35 | 0.0297 (14) | 0.0337 (18) | 0.0318 (15) | 0.0009 (13) | 0.0027 (12) | 0.0068 (13) |
C36 | 0.0311 (14) | 0.0226 (16) | 0.0338 (14) | 0.0009 (11) | 0.0063 (12) | 0.0046 (13) |
C41 | 0.0296 (13) | 0.0135 (13) | 0.0251 (12) | 0.0009 (10) | 0.0101 (11) | −0.0012 (11) |
C42 | 0.0298 (13) | 0.0221 (15) | 0.0276 (13) | −0.0013 (11) | 0.0079 (11) | −0.0017 (12) |
C43 | 0.0381 (15) | 0.0249 (15) | 0.0254 (13) | −0.0028 (12) | 0.0081 (12) | −0.0057 (12) |
C44 | 0.0474 (17) | 0.0202 (16) | 0.0307 (14) | 0.0018 (12) | 0.0182 (13) | −0.0028 (12) |
C45 | 0.0332 (15) | 0.0304 (16) | 0.0409 (16) | 0.0040 (12) | 0.0167 (13) | −0.0020 (14) |
C46 | 0.0294 (13) | 0.0237 (15) | 0.0296 (14) | −0.0021 (11) | 0.0086 (11) | −0.0001 (12) |
Br | 0.0328 (2) | 0.0190 (2) | 0.0298 (2) | −0.00069 (10) | 0.00723 (14) | 0.00004 (11) |
P | 0.0224 (3) | 0.0154 (4) | 0.0223 (3) | −0.0005 (2) | 0.0052 (3) | −0.0010 (3) |
C11—C12 | 1.541 (4) | C31—C32 | 1.391 (4) |
C11—P | 1.791 (3) | C31—C36 | 1.393 (4) |
C11—H11A | 0.99 | C31—P | 1.799 (2) |
C11—H11B | 0.99 | C32—C33 | 1.392 (4) |
C12—C13 | 1.526 (3) | C32—H32 | 0.95 |
C12—C14 | 1.539 (4) | C33—C34 | 1.376 (4) |
C12—H12 | 1 | C33—H33 | 0.95 |
C13—H13A | 0.98 | C34—C35 | 1.389 (4) |
C13—H13B | 0.98 | C34—H34 | 0.95 |
C13—H13C | 0.98 | C35—C36 | 1.378 (4) |
C14—H14A | 0.98 | C35—H35 | 0.95 |
C14—H14B | 0.98 | C36—H36 | 0.95 |
C14—H14C | 0.98 | C41—C46 | 1.384 (4) |
C21—C22 | 1.398 (4) | C41—C42 | 1.404 (4) |
C21—C26 | 1.398 (4) | C41—P | 1.798 (3) |
C21—P | 1.801 (3) | C42—C43 | 1.385 (4) |
C22—C23 | 1.392 (4) | C42—H42 | 0.95 |
C22—H22 | 0.95 | C43—C44 | 1.379 (4) |
C23—C24 | 1.386 (4) | C43—H43 | 0.95 |
C23—H23 | 0.95 | C44—C45 | 1.385 (4) |
C24—C25 | 1.382 (4) | C44—H44 | 0.95 |
C24—H24 | 0.95 | C45—C46 | 1.394 (4) |
C25—C26 | 1.383 (4) | C45—H45 | 0.95 |
C25—H25 | 0.95 | C46—H46 | 0.95 |
C26—H26 | 0.95 | ||
C12—C11—P | 116.77 (18) | C32—C31—C36 | 119.6 (2) |
C12—C11—H11A | 108.1 | C32—C31—P | 121.77 (19) |
P—C11—H11A | 108.1 | C36—C31—P | 118.6 (2) |
C12—C11—H11B | 108.1 | C31—C32—C33 | 119.7 (3) |
P—C11—H11B | 108.1 | C31—C32—H32 | 120.2 |
H11A—C11—H11B | 107.3 | C33—C32—H32 | 120.2 |
C13—C12—C14 | 110.0 (2) | C34—C33—C32 | 120.0 (3) |
C13—C12—C11 | 110.9 (2) | C34—C33—H33 | 120 |
C14—C12—C11 | 110.2 (2) | C32—C33—H33 | 120 |
C13—C12—H12 | 108.6 | C33—C34—C35 | 120.7 (2) |
C14—C12—H12 | 108.6 | C33—C34—H34 | 119.6 |
C11—C12—H12 | 108.6 | C35—C34—H34 | 119.6 |
C12—C13—H13A | 109.5 | C36—C35—C34 | 119.4 (3) |
C12—C13—H13B | 109.5 | C36—C35—H35 | 120.3 |
H13A—C13—H13B | 109.5 | C34—C35—H35 | 120.3 |
C12—C13—H13C | 109.5 | C35—C36—C31 | 120.6 (3) |
H13A—C13—H13C | 109.5 | C35—C36—H36 | 119.7 |
H13B—C13—H13C | 109.5 | C31—C36—H36 | 119.7 |
C12—C14—H14A | 109.5 | C46—C41—C42 | 120.1 (2) |
C12—C14—H14B | 109.5 | C46—C41—P | 122.40 (19) |
H14A—C14—H14B | 109.5 | C42—C41—P | 117.4 (2) |
C12—C14—H14C | 109.5 | C43—C42—C41 | 119.1 (3) |
H14A—C14—H14C | 109.5 | C43—C42—H42 | 120.5 |
H14B—C14—H14C | 109.5 | C41—C42—H42 | 120.5 |
C22—C21—C26 | 119.9 (2) | C44—C43—C42 | 121.0 (2) |
C22—C21—P | 117.8 (2) | C44—C43—H43 | 119.5 |
C26—C21—P | 122.20 (19) | C42—C43—H43 | 119.5 |
C23—C22—C21 | 119.5 (3) | C43—C44—C45 | 119.9 (3) |
C23—C22—H22 | 120.3 | C43—C44—H44 | 120.1 |
C21—C22—H22 | 120.3 | C45—C44—H44 | 120.1 |
C24—C23—C22 | 120.0 (3) | C44—C45—C46 | 120.1 (3) |
C24—C23—H23 | 120 | C44—C45—H45 | 120 |
C22—C23—H23 | 120 | C46—C45—H45 | 120 |
C25—C24—C23 | 120.6 (3) | C41—C46—C45 | 119.9 (2) |
C25—C24—H24 | 119.7 | C41—C46—H46 | 120.1 |
C23—C24—H24 | 119.7 | C45—C46—H46 | 120.1 |
C24—C25—C26 | 120.0 (3) | C11—P—C41 | 112.00 (12) |
C24—C25—H25 | 120 | C11—P—C31 | 111.26 (12) |
C26—C25—H25 | 120 | C41—P—C31 | 109.71 (12) |
C25—C26—C21 | 120.0 (3) | C11—P—C21 | 110.30 (12) |
C25—C26—H26 | 120 | C41—P—C21 | 107.68 (12) |
C21—C26—H26 | 120 | C31—P—C21 | 105.65 (12) |
P—C11—C12—C13 | −102.2 (2) | P—C41—C46—C45 | −175.6 (2) |
P—C11—C12—C14 | 135.71 (19) | C44—C45—C46—C41 | 1.1 (4) |
C26—C21—C22—C23 | 0.4 (4) | C12—C11—P—C41 | 52.7 (2) |
P—C21—C22—C23 | 176.2 (2) | C12—C11—P—C31 | −70.5 (2) |
C21—C22—C23—C24 | −0.9 (4) | C12—C11—P—C21 | 172.64 (18) |
C22—C23—C24—C25 | 1.5 (4) | C46—C41—P—C11 | −126.9 (2) |
C23—C24—C25—C26 | −1.6 (4) | C42—C41—P—C11 | 56.8 (2) |
C24—C25—C26—C21 | 1.1 (4) | C46—C41—P—C31 | −2.8 (3) |
C22—C21—C26—C25 | −0.5 (4) | C42—C41—P—C31 | −179.1 (2) |
P—C21—C26—C25 | −176.11 (19) | C46—C41—P—C21 | 111.7 (2) |
C36—C31—C32—C33 | −0.8 (4) | C42—C41—P—C21 | −64.6 (2) |
P—C31—C32—C33 | −178.6 (2) | C32—C31—P—C11 | 9.5 (3) |
C31—C32—C33—C34 | 0.8 (4) | C36—C31—P—C11 | −168.3 (2) |
C32—C33—C34—C35 | −0.5 (4) | C32—C31—P—C41 | −115.0 (2) |
C33—C34—C35—C36 | 0.3 (4) | C36—C31—P—C41 | 67.2 (2) |
C34—C35—C36—C31 | −0.3 (4) | C32—C31—P—C21 | 129.2 (2) |
C32—C31—C36—C35 | 0.6 (4) | C36—C31—P—C21 | −48.6 (3) |
P—C31—C36—C35 | 178.4 (2) | C22—C21—P—C11 | 56.3 (2) |
C46—C41—C42—C43 | −2.0 (4) | C26—C21—P—C11 | −128.0 (2) |
P—C41—C42—C43 | 174.3 (2) | C22—C21—P—C41 | 178.76 (19) |
C41—C42—C43—C44 | 1.8 (4) | C26—C21—P—C41 | −5.5 (2) |
C42—C43—C44—C45 | −0.1 (4) | C22—C21—P—C31 | −64.1 (2) |
C43—C44—C45—C46 | −1.3 (4) | C26—C21—P—C31 | 111.7 (2) |
C42—C41—C46—C45 | 0.6 (4) |
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