Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022197/cf2033sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022197/cf2033Isup2.hkl |
CCDC reference: 613628
Key indicators
- Single-crystal X-ray study
- T = 102 K
- Mean (C-C) = 0.004 Å
- R factor = 0.038
- wR factor = 0.105
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
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−·CH4O | F(000) = 928 |
Mr = 445.36 | Dx = 1.326 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 22024 reflections |
a = 8.7797 (1) Å | θ = 3.2–68.1° |
b = 18.3601 (5) Å | µ = 3.26 mm−1 |
c = 14.6181 (3) Å | T = 102 K |
β = 108.775 (1)° | Prism, colorless |
V = 2231.00 (8) Å3 | 0.4 × 0.35 × 0.35 mm |
Z = 4 |
Bruker SMART diffractometer | 3546 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.068 |
Göbel focusing mirrors monochromator | θmax = 68.3°, θmin = 4° |
Detector resolution: 17 pixels mm-1 | h = −10→10 |
ω scans | k = −15→22 |
22024 measured reflections | l = −14→17 |
4074 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.058P)2 + 2.401P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.105 | (Δ/σ)max = 0.026 |
S = 1.04 | Δρmax = 0.9 e Å−3 |
4074 reflections | Δρmin = −0.77 e Å−3 |
248 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 | ||
O1 | 0.8120 (3) | 0.91542 (16) | 0.0846 (2) | 0.0555 (7) | |
H1 | 0.8593 | 0.8804 | 0.116 | 0.083* | |
C1 | 0.6687 (4) | 0.9249 (2) | 0.1007 (3) | 0.0510 (9) | |
H1A | 0.6872 | 0.9465 | 0.1631 | 0.076* | |
H1B | 0.6169 | 0.8786 | 0.0984 | 0.076* | |
H1C | 0.601 | 0.9563 | 0.0519 | 0.076* | |
Br | 0.97485 (4) | 0.764078 (16) | 0.20073 (2) | 0.02757 (12) | |
C11 | 0.1718 (3) | 0.72606 (14) | −0.0122 (2) | 0.0217 (6) | |
H11A | 0.1184 | 0.7328 | −0.0809 | 0.026* | |
H11B | 0.0902 | 0.7136 | 0.0167 | 0.026* | |
C12 | 0.2509 (3) | 0.79852 (15) | 0.03144 (19) | 0.0220 (6) | |
H12A | 0.3014 | 0.7924 | 0.1005 | 0.026* | |
H12B | 0.3345 | 0.8106 | 0.0039 | 0.026* | |
C13 | 0.1310 (3) | 0.86148 (15) | 0.01334 (19) | 0.0232 (6) | |
H13 | 0.0368 | 0.8446 | 0.0294 | 0.028* | |
C14 | 0.2039 (4) | 0.92514 (16) | 0.0792 (2) | 0.0339 (7) | |
H14A | 0.2324 | 0.9098 | 0.1454 | 0.051* | |
H14B | 0.1269 | 0.964 | 0.0678 | 0.051* | |
H14C | 0.2983 | 0.9418 | 0.0661 | 0.051* | |
C15 | 0.0741 (5) | 0.88602 (19) | −0.0916 (2) | 0.0441 (9) | |
H15A | −0.0073 | 0.9227 | −0.1005 | 0.066* | |
H15B | 0.0304 | 0.8451 | −0.1326 | 0.066* | |
H15C | 0.1633 | 0.9057 | −0.1079 | 0.066* | |
C21 | 0.2009 (3) | 0.57030 (15) | −0.0472 (2) | 0.0227 (6) | |
C22 | 0.0935 (3) | 0.57210 (16) | −0.1419 (2) | 0.0279 (6) | |
H22 | 0.0737 | 0.6156 | −0.1763 | 0.034* | |
C23 | 0.0172 (4) | 0.50870 (18) | −0.1840 (2) | 0.0353 (7) | |
H23 | −0.053 | 0.5097 | −0.2471 | 0.042* | |
C24 | 0.0445 (4) | 0.44406 (17) | −0.1331 (3) | 0.0355 (7) | |
H24 | −0.005 | 0.4014 | −0.1624 | 0.043* | |
C25 | 0.1449 (4) | 0.44271 (16) | −0.0391 (2) | 0.0334 (7) | |
H25 | 0.1595 | 0.3994 | −0.0044 | 0.04* | |
C26 | 0.2250 (3) | 0.50502 (15) | 0.0049 (2) | 0.0252 (6) | |
H26 | 0.2939 | 0.5034 | 0.0683 | 0.03* | |
C31 | 0.4597 (3) | 0.67121 (15) | −0.05273 (19) | 0.0221 (6) | |
C32 | 0.5879 (3) | 0.71712 (15) | −0.0068 (2) | 0.0231 (6) | |
H32 | 0.6004 | 0.7345 | 0.055 | 0.028* | |
C33 | 0.6971 (3) | 0.73694 (16) | −0.0532 (2) | 0.0278 (6) | |
H33 | 0.7818 | 0.7681 | −0.0227 | 0.033* | |
C34 | 0.6808 (4) | 0.71064 (19) | −0.1445 (2) | 0.0333 (7) | |
H34 | 0.754 | 0.7241 | −0.1754 | 0.04* | |
C35 | 0.5551 (4) | 0.6643 (2) | −0.1894 (2) | 0.0372 (8) | |
H35 | 0.5449 | 0.6461 | −0.2504 | 0.045* | |
C36 | 0.4440 (4) | 0.64462 (17) | −0.1448 (2) | 0.0305 (7) | |
H36 | 0.3591 | 0.6138 | −0.176 | 0.037* | |
C41 | 0.4133 (3) | 0.63492 (15) | 0.13058 (19) | 0.0215 (6) | |
C42 | 0.3462 (3) | 0.65663 (15) | 0.2009 (2) | 0.0238 (6) | |
H42 | 0.2496 | 0.6822 | 0.1835 | 0.029* | |
C43 | 0.4248 (4) | 0.63976 (17) | 0.2965 (2) | 0.0310 (7) | |
H43 | 0.3816 | 0.655 | 0.3436 | 0.037* | |
C44 | 0.5673 (4) | 0.60037 (17) | 0.3234 (2) | 0.0328 (7) | |
H44 | 0.6183 | 0.5889 | 0.388 | 0.039* | |
C45 | 0.6333 (4) | 0.57827 (18) | 0.2538 (2) | 0.0340 (7) | |
H45 | 0.7288 | 0.5519 | 0.2716 | 0.041* | |
C46 | 0.5567 (3) | 0.59554 (16) | 0.1570 (2) | 0.0279 (6) | |
H46 | 0.6012 | 0.5808 | 0.1102 | 0.033* | |
P | 0.31084 (8) | 0.65095 (4) | 0.00482 (5) | 0.01877 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0577 (16) | 0.0567 (17) | 0.0608 (17) | 0.0130 (13) | 0.0310 (14) | 0.0135 (13) |
C1 | 0.043 (2) | 0.064 (3) | 0.050 (2) | 0.0034 (18) | 0.0210 (17) | 0.0095 (18) |
Br | 0.03312 (19) | 0.02729 (19) | 0.02462 (18) | 0.00421 (12) | 0.01253 (13) | 0.00066 (11) |
C11 | 0.0185 (12) | 0.0212 (14) | 0.0252 (14) | 0.0026 (11) | 0.0066 (10) | 0.0003 (11) |
C12 | 0.0230 (13) | 0.0202 (14) | 0.0214 (13) | 0.0009 (11) | 0.0053 (10) | −0.0009 (11) |
C13 | 0.0227 (13) | 0.0224 (14) | 0.0259 (14) | 0.0028 (11) | 0.0096 (11) | −0.0013 (11) |
C14 | 0.0411 (17) | 0.0235 (15) | 0.0323 (16) | 0.0054 (13) | 0.0052 (13) | −0.0061 (12) |
C15 | 0.062 (2) | 0.0311 (17) | 0.0302 (17) | 0.0188 (17) | 0.0015 (15) | −0.0014 (14) |
C21 | 0.0222 (13) | 0.0208 (14) | 0.0282 (14) | 0.0000 (11) | 0.0128 (11) | −0.0029 (11) |
C22 | 0.0300 (15) | 0.0238 (15) | 0.0307 (15) | −0.0012 (12) | 0.0106 (12) | −0.0002 (12) |
C23 | 0.0308 (16) | 0.0382 (18) | 0.0360 (17) | −0.0050 (14) | 0.0094 (13) | −0.0114 (14) |
C24 | 0.0314 (16) | 0.0259 (16) | 0.055 (2) | −0.0078 (13) | 0.0222 (15) | −0.0150 (15) |
C25 | 0.0332 (16) | 0.0202 (15) | 0.056 (2) | 0.0036 (12) | 0.0277 (15) | 0.0045 (14) |
C26 | 0.0245 (13) | 0.0226 (14) | 0.0331 (15) | 0.0037 (11) | 0.0154 (11) | 0.0025 (12) |
C31 | 0.0234 (13) | 0.0231 (14) | 0.0223 (13) | 0.0045 (11) | 0.0106 (11) | 0.0044 (11) |
C32 | 0.0222 (13) | 0.0238 (14) | 0.0232 (14) | 0.0031 (11) | 0.0073 (11) | 0.0003 (11) |
C33 | 0.0210 (14) | 0.0294 (16) | 0.0337 (16) | 0.0004 (12) | 0.0099 (12) | 0.0057 (12) |
C34 | 0.0282 (15) | 0.0428 (18) | 0.0332 (16) | 0.0064 (14) | 0.0161 (12) | 0.0122 (14) |
C35 | 0.0381 (17) | 0.053 (2) | 0.0242 (15) | 0.0022 (15) | 0.0152 (13) | −0.0010 (14) |
C36 | 0.0291 (15) | 0.0395 (18) | 0.0241 (14) | −0.0032 (13) | 0.0100 (12) | −0.0047 (13) |
C41 | 0.0241 (13) | 0.0223 (14) | 0.0190 (12) | −0.0013 (11) | 0.0082 (10) | −0.0002 (10) |
C42 | 0.0241 (13) | 0.0235 (14) | 0.0271 (14) | −0.0011 (11) | 0.0130 (11) | −0.0032 (11) |
C43 | 0.0422 (17) | 0.0334 (17) | 0.0231 (14) | −0.0049 (14) | 0.0184 (13) | −0.0031 (12) |
C44 | 0.0413 (17) | 0.0330 (17) | 0.0215 (14) | −0.0026 (14) | 0.0066 (12) | 0.0041 (12) |
C45 | 0.0299 (15) | 0.0387 (18) | 0.0304 (16) | 0.0063 (14) | 0.0053 (12) | 0.0077 (13) |
C46 | 0.0281 (14) | 0.0322 (16) | 0.0247 (14) | 0.0066 (12) | 0.0106 (11) | 0.0033 (12) |
P | 0.0199 (3) | 0.0185 (3) | 0.0187 (3) | 0.0016 (3) | 0.0071 (3) | 0.0000 (2) |
O1—C1 | 1.364 (4) | C24—H24 | 0.93 |
O1—H1 | 0.82 | C25—C26 | 1.388 (4) |
C1—H1A | 0.96 | C25—H25 | 0.93 |
C1—H1B | 0.96 | C26—H26 | 0.93 |
C1—H1C | 0.96 | C31—C32 | 1.394 (4) |
C11—C12 | 1.541 (4) | C31—C36 | 1.396 (4) |
C11—P | 1.805 (3) | C31—P | 1.806 (3) |
C11—H11A | 0.97 | C32—C33 | 1.390 (4) |
C11—H11B | 0.97 | C32—H32 | 0.93 |
C12—C13 | 1.528 (4) | C33—C34 | 1.382 (5) |
C12—H12A | 0.97 | C33—H33 | 0.93 |
C12—H12B | 0.97 | C34—C35 | 1.381 (5) |
C13—C14 | 1.519 (4) | C34—H34 | 0.93 |
C13—C15 | 1.521 (4) | C35—C36 | 1.385 (4) |
C13—H13 | 0.98 | C35—H35 | 0.93 |
C14—H14A | 0.96 | C36—H36 | 0.93 |
C14—H14B | 0.96 | C41—C46 | 1.395 (4) |
C14—H14C | 0.96 | C41—C42 | 1.398 (4) |
C15—H15A | 0.96 | C41—P | 1.792 (3) |
C15—H15B | 0.96 | C42—C43 | 1.379 (4) |
C15—H15C | 0.96 | C42—H42 | 0.93 |
C21—C26 | 1.399 (4) | C43—C44 | 1.388 (5) |
C21—C22 | 1.403 (4) | C43—H43 | 0.93 |
C21—P | 1.797 (3) | C44—C45 | 1.383 (5) |
C22—C23 | 1.384 (4) | C44—H44 | 0.93 |
C22—H22 | 0.93 | C45—C46 | 1.393 (4) |
C23—C24 | 1.381 (5) | C45—H45 | 0.93 |
C23—H23 | 0.93 | C46—H46 | 0.93 |
C24—C25 | 1.373 (5) | ||
C1—O1—H1 | 109.5 | C24—C25—C26 | 121.0 (3) |
O1—C1—H1A | 109.5 | C24—C25—H25 | 119.5 |
O1—C1—H1B | 109.5 | C26—C25—H25 | 119.5 |
H1A—C1—H1B | 109.5 | C25—C26—C21 | 119.2 (3) |
O1—C1—H1C | 109.5 | C25—C26—H26 | 120.4 |
H1A—C1—H1C | 109.5 | C21—C26—H26 | 120.4 |
H1B—C1—H1C | 109.5 | C32—C31—C36 | 119.3 (3) |
C12—C11—P | 114.08 (18) | C32—C31—P | 119.6 (2) |
C12—C11—H11A | 108.7 | C36—C31—P | 121.0 (2) |
P—C11—H11A | 108.7 | C33—C32—C31 | 120.0 (3) |
C12—C11—H11B | 108.7 | C33—C32—H32 | 120 |
P—C11—H11B | 108.7 | C31—C32—H32 | 120 |
H11A—C11—H11B | 107.6 | C34—C33—C32 | 120.4 (3) |
C13—C12—C11 | 112.8 (2) | C34—C33—H33 | 119.8 |
C13—C12—H12A | 109 | C32—C33—H33 | 119.8 |
C11—C12—H12A | 109 | C35—C34—C33 | 119.6 (3) |
C13—C12—H12B | 109 | C35—C34—H34 | 120.2 |
C11—C12—H12B | 109 | C33—C34—H34 | 120.2 |
H12A—C12—H12B | 107.8 | C34—C35—C36 | 120.9 (3) |
C14—C13—C15 | 110.2 (2) | C34—C35—H35 | 119.6 |
C14—C13—C12 | 110.3 (2) | C36—C35—H35 | 119.6 |
C15—C13—C12 | 112.5 (2) | C35—C36—C31 | 119.8 (3) |
C14—C13—H13 | 107.9 | C35—C36—H36 | 120.1 |
C15—C13—H13 | 107.9 | C31—C36—H36 | 120.1 |
C12—C13—H13 | 107.9 | C46—C41—C42 | 120.1 (2) |
C13—C14—H14A | 109.5 | C46—C41—P | 118.7 (2) |
C13—C14—H14B | 109.5 | C42—C41—P | 121.1 (2) |
H14A—C14—H14B | 109.5 | C43—C42—C41 | 119.3 (3) |
C13—C14—H14C | 109.5 | C43—C42—H42 | 120.4 |
H14A—C14—H14C | 109.5 | C41—C42—H42 | 120.4 |
H14B—C14—H14C | 109.5 | C42—C43—C44 | 121.0 (3) |
C13—C15—H15A | 109.5 | C42—C43—H43 | 119.5 |
C13—C15—H15B | 109.5 | C44—C43—H43 | 119.5 |
H15A—C15—H15B | 109.5 | C45—C44—C43 | 119.8 (3) |
C13—C15—H15C | 109.5 | C45—C44—H44 | 120.1 |
H15A—C15—H15C | 109.5 | C43—C44—H44 | 120.1 |
H15B—C15—H15C | 109.5 | C44—C45—C46 | 120.0 (3) |
C26—C21—C22 | 119.6 (3) | C44—C45—H45 | 120 |
C26—C21—P | 120.6 (2) | C46—C45—H45 | 120 |
C22—C21—P | 119.8 (2) | C45—C46—C41 | 119.8 (3) |
C23—C22—C21 | 119.6 (3) | C45—C46—H46 | 120.1 |
C23—C22—H22 | 120.2 | C41—C46—H46 | 120.1 |
C21—C22—H22 | 120.2 | C41—P—C21 | 108.82 (13) |
C24—C23—C22 | 120.5 (3) | C41—P—C11 | 111.17 (13) |
C24—C23—H23 | 119.7 | C21—P—C11 | 108.89 (12) |
C22—C23—H23 | 119.7 | C41—P—C31 | 108.19 (12) |
C25—C24—C23 | 120.0 (3) | C21—P—C31 | 110.09 (13) |
C25—C24—H24 | 120 | C11—P—C31 | 109.68 (13) |
C23—C24—H24 | 120 | ||
P—C11—C12—C13 | 178.37 (19) | C44—C45—C46—C41 | −0.2 (5) |
C11—C12—C13—C14 | 164.9 (2) | C42—C41—C46—C45 | −0.4 (4) |
C11—C12—C13—C15 | −71.6 (3) | P—C41—C46—C45 | −175.9 (2) |
C26—C21—C22—C23 | −2.4 (4) | C46—C41—P—C21 | 79.6 (2) |
P—C21—C22—C23 | 175.7 (2) | C42—C41—P—C21 | −95.9 (2) |
C21—C22—C23—C24 | 0.8 (5) | C46—C41—P—C11 | −160.5 (2) |
C22—C23—C24—C25 | 1.6 (5) | C42—C41—P—C11 | 24.0 (3) |
C23—C24—C25—C26 | −2.5 (5) | C46—C41—P—C31 | −40.0 (3) |
C24—C25—C26—C21 | 0.9 (4) | C42—C41—P—C31 | 144.5 (2) |
C22—C21—C26—C25 | 1.5 (4) | C26—C21—P—C41 | −10.4 (3) |
P—C21—C26—C25 | −176.5 (2) | C22—C21—P—C41 | 171.6 (2) |
C36—C31—C32—C33 | 1.0 (4) | C26—C21—P—C11 | −131.7 (2) |
P—C31—C32—C33 | −175.7 (2) | C22—C21—P—C11 | 50.3 (3) |
C31—C32—C33—C34 | −0.8 (4) | C26—C21—P—C31 | 108.0 (2) |
C32—C33—C34—C35 | −0.1 (5) | C22—C21—P—C31 | −70.0 (2) |
C33—C34—C35—C36 | 0.9 (5) | C12—C11—P—C41 | 58.8 (2) |
C34—C35—C36—C31 | −0.7 (5) | C12—C11—P—C21 | 178.68 (19) |
C32—C31—C36—C35 | −0.3 (4) | C12—C11—P—C31 | −60.8 (2) |
P—C31—C36—C35 | 176.4 (2) | C32—C31—P—C41 | −42.4 (2) |
C46—C41—C42—C43 | 1.1 (4) | C36—C31—P—C41 | 140.9 (2) |
P—C41—C42—C43 | 176.5 (2) | C32—C31—P—C21 | −161.2 (2) |
C41—C42—C43—C44 | −1.3 (4) | C36—C31—P—C21 | 22.1 (3) |
C42—C43—C44—C45 | 0.8 (5) | C32—C31—P—C11 | 79.0 (2) |
C43—C44—C45—C46 | 0.0 (5) | C36—C31—P—C11 | −97.7 (2) |