Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053548/hk2349sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053548/hk2349Isup2.hkl |
CCDC reference: 672808
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.013 Å
- R factor = 0.084
- wR factor = 0.196
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C46 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.36 Ang. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 13 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C23 H24 O2 P PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C23 H24 O2 P
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 121
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Mashraqui et al. (2004); Ishikawa & Manabe (2006). For bond-length data, see: Allen et al. (1987).
For the preparation of the title copound, (I), a mixture of 5-bromovaleric acid (2.4613 g, 9 mmol) and triphenylphosphine (3.6076 g, 9 mmol) was heated under reflux in acetonitrile (100 ml) for 24 h. The resulting salt was recrystallized from acetonitrile, washed with ether, and dried in vacuum to give the title compound (yield; 2.5994 g). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.
H atoms were positioned geometrically, with O—H = 0.82 Å (for OH) and C—H = 0.93 and 0.97 Å for aromatic and methylene H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.5 for OH H, and x = 1.2 for all other H atoms.
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: X-CAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).
C23H24O2P+·Br− | Z = 4 |
Mr = 443.29 | F(000) = 912 |
Triclinic, P1 | Dx = 1.379 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2690 (19) Å | Cell parameters from 25 reflections |
b = 13.674 (3) Å | θ = 9–13° |
c = 17.075 (3) Å | µ = 2.02 mm−1 |
α = 88.91 (3)° | T = 294 K |
β = 87.15 (3)° | Block, colourless |
γ = 81.07 (3)° | 0.30 × 0.20 × 0.10 mm |
V = 2135.1 (8) Å3 |
Enraf–Nonius CAD-4 diffractometer | 3700 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.055 |
Graphite monochromator | θmax = 26.0°, θmin = 1.2° |
ω/2θ scans | h = −11→11 |
Absorption correction: ψ scan (North et al., 1968) | k = −16→16 |
Tmin = 0.583, Tmax = 0.824 | l = 0→21 |
8913 measured reflections | 3 standard reflections every 120 min |
8367 independent reflections | intensity decay: none |
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)] = 0.084 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.196 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.05P)2 + 8P] where P = (Fo2 + 2Fc2)/3 |
8367 reflections | (Δ/σ)max < 0.001 |
475 parameters | Δρmax = 0.72 e Å−3 |
121 restraints | Δρmin = −0.60 e Å−3 |
C23H24O2P+·Br− | γ = 81.07 (3)° |
Mr = 443.29 | V = 2135.1 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.2690 (19) Å | Mo Kα radiation |
b = 13.674 (3) Å | µ = 2.02 mm−1 |
c = 17.075 (3) Å | T = 294 K |
α = 88.91 (3)° | 0.30 × 0.20 × 0.10 mm |
β = 87.15 (3)° |
Enraf–Nonius CAD-4 diffractometer | 3700 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.055 |
Tmin = 0.583, Tmax = 0.824 | 3 standard reflections every 120 min |
8913 measured reflections | intensity decay: none |
8367 independent reflections |
R[F2 > 2σ(F2)] = 0.084 | 121 restraints |
wR(F2) = 0.196 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.72 e Å−3 |
8367 reflections | Δρmin = −0.60 e Å−3 |
475 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 | 0.75038 (14) | 0.91104 (8) | 0.16509 (6) | 0.0872 (4) | |
P1 | 1.2962 (2) | 1.04654 (14) | 0.31701 (12) | 0.0425 (5) | |
O1 | 1.0624 (8) | 1.0797 (4) | 0.6324 (4) | 0.080 (2) | |
O2 | 1.1257 (8) | 1.2101 (4) | 0.6878 (4) | 0.086 (2) | |
H2B | 1.1520 | 1.1693 | 0.7221 | 0.129* | |
C1 | 1.3356 (12) | 1.0358 (8) | 0.0821 (6) | 0.091 (3) | |
H1A | 1.4095 | 1.0416 | 0.0442 | 0.110* | |
C2 | 1.3601 (11) | 1.0448 (7) | 0.1601 (6) | 0.077 (3) | |
H2A | 1.4507 | 1.0583 | 0.1740 | 0.093* | |
C3 | 1.2581 (9) | 1.0349 (6) | 0.2169 (5) | 0.048 (2) | |
C4 | 1.1218 (9) | 1.0171 (6) | 0.1935 (5) | 0.055 (2) | |
H4A | 1.0466 | 1.0127 | 0.2309 | 0.066* | |
C5 | 1.0996 (11) | 1.0062 (7) | 0.1173 (6) | 0.077 (3) | |
H5A | 1.0105 | 0.9899 | 0.1036 | 0.092* | |
C6 | 1.2000 (12) | 1.0179 (7) | 0.0602 (6) | 0.080 (3) | |
H6A | 1.1795 | 1.0142 | 0.0076 | 0.096* | |
C7 | 1.3757 (12) | 0.7501 (7) | 0.3593 (6) | 0.084 (3) | |
H7A | 1.3615 | 0.6925 | 0.3346 | 0.101* | |
C8 | 1.3386 (10) | 0.8424 (7) | 0.3196 (6) | 0.071 | |
H8A | 1.3086 | 0.8453 | 0.2683 | 0.085* | |
C9 | 1.3489 (8) | 0.9279 (5) | 0.3602 (5) | 0.0442 (19) | |
C10 | 1.4013 (10) | 0.9180 (6) | 0.4333 (5) | 0.063 (2) | |
H10A | 1.4105 | 0.9749 | 0.4605 | 0.075* | |
C11 | 1.4414 (10) | 0.8272 (7) | 0.4686 (5) | 0.067 (2) | |
H11A | 1.4764 | 0.8237 | 0.5189 | 0.080* | |
C12 | 1.4300 (10) | 0.7428 (7) | 0.4303 (6) | 0.069 (3) | |
H12A | 1.4595 | 0.6812 | 0.4532 | 0.083* | |
C13 | 1.6691 (9) | 1.2263 (6) | 0.3333 (5) | 0.053 (2) | |
H13A | 1.7452 | 1.2627 | 0.3374 | 0.063* | |
C14 | 1.6956 (9) | 1.1236 (6) | 0.3317 (5) | 0.055 (2) | |
H14A | 1.7912 | 1.0909 | 0.3332 | 0.066* | |
C15 | 1.5840 (9) | 1.0697 (6) | 0.3279 (5) | 0.048 (2) | |
H15A | 1.6044 | 1.0009 | 0.3277 | 0.057* | |
C16 | 1.4439 (8) | 1.1154 (5) | 0.3244 (4) | 0.0404 (19) | |
C17 | 1.4149 (8) | 1.2191 (5) | 0.3242 (5) | 0.048 (2) | |
H17A | 1.3194 | 1.2515 | 0.3209 | 0.058* | |
C18 | 1.5273 (9) | 1.2726 (6) | 0.3287 (5) | 0.052 (2) | |
H18A | 1.5072 | 1.3414 | 0.3287 | 0.062* | |
C19 | 1.1305 (8) | 1.1083 (5) | 0.3668 (5) | 0.046 (2) | |
H19A | 1.0938 | 1.1670 | 0.3367 | 0.055* | |
H19B | 1.0574 | 1.0646 | 0.3672 | 0.055* | |
C20 | 1.1476 (8) | 1.1391 (6) | 0.4518 (5) | 0.053 (2) | |
H20A | 1.1855 | 1.0813 | 0.4826 | 0.064* | |
H20B | 1.2169 | 1.1854 | 0.4522 | 0.064* | |
C21 | 1.0021 (9) | 1.1868 (6) | 0.4880 (5) | 0.061 (2) | |
H21A | 0.9393 | 1.1367 | 0.4969 | 0.073* | |
H21B | 0.9553 | 1.2358 | 0.4518 | 0.073* | |
C22 | 1.0196 (10) | 1.2365 (6) | 0.5659 (5) | 0.061 (2) | |
H22A | 1.0889 | 1.2825 | 0.5573 | 0.073* | |
H22B | 0.9263 | 1.2746 | 0.5826 | 0.073* | |
C23 | 1.0709 (9) | 1.1661 (6) | 0.6308 (5) | 0.052 (2) | |
Br2 | 0.05878 (11) | 0.37271 (7) | 0.29062 (6) | 0.0675 (3) | |
P2 | −0.3584 (2) | 0.53719 (15) | 0.15327 (12) | 0.0433 (5) | |
O3 | −0.3181 (9) | 0.4922 (6) | 0.5941 (4) | 0.106 (3) | |
O4 | −0.1554 (8) | 0.5727 (5) | 0.5404 (4) | 0.090 (2) | |
H4B | −0.1504 | 0.5891 | 0.5860 | 0.135* | |
C24 | −0.8304 (12) | 0.6946 (9) | 0.1678 (7) | 0.083 (3) | |
H24A | −0.9253 | 0.7288 | 0.1720 | 0.100* | |
C25 | −0.7298 (13) | 0.7270 (8) | 0.1165 (6) | 0.087 (3) | |
H25A | −0.7584 | 0.7824 | 0.0852 | 0.105* | |
C26 | −0.5902 (11) | 0.6808 (7) | 0.1098 (5) | 0.070 (3) | |
H26A | −0.5242 | 0.7037 | 0.0737 | 0.083* | |
C27 | −0.5446 (9) | 0.5969 (6) | 0.1581 (5) | 0.046 (2) | |
C28 | −0.6490 (10) | 0.5632 (6) | 0.2094 (5) | 0.057 (2) | |
H28A | −0.6225 | 0.5078 | 0.2410 | 0.068* | |
C29 | −0.7921 (11) | 0.6120 (8) | 0.2133 (6) | 0.070 (3) | |
H29A | −0.8617 | 0.5887 | 0.2467 | 0.084* | |
C30 | −0.4604 (11) | 0.2666 (7) | 0.1041 (6) | 0.076 (3) | |
H30A | −0.5396 | 0.2407 | 0.0862 | 0.091* | |
C31 | −0.4702 (10) | 0.3675 (6) | 0.1175 (5) | 0.062 (2) | |
H31A | −0.5568 | 0.4095 | 0.1081 | 0.074* | |
C32 | −0.3532 (8) | 0.4058 (5) | 0.1444 (4) | 0.0377 (18) | |
C33 | −0.2246 (9) | 0.3432 (6) | 0.1582 (5) | 0.051 (2) | |
H33A | −0.1451 | 0.3684 | 0.1765 | 0.061* | |
C34 | −0.2146 (10) | 0.2429 (6) | 0.1447 (6) | 0.065 (3) | |
H34A | −0.1283 | 0.2007 | 0.1540 | 0.078* | |
C35 | −0.3312 (11) | 0.2059 (6) | 0.1178 (5) | 0.065 (3) | |
H35A | −0.3231 | 0.1384 | 0.1086 | 0.078* | |
C36 | −0.1545 (11) | 0.7136 (7) | 0.0082 (6) | 0.073 (3) | |
H36A | −0.1283 | 0.7764 | 0.0099 | 0.088* | |
C37 | −0.2211 (10) | 0.6756 (6) | 0.0734 (5) | 0.061 (2) | |
H37A | −0.2398 | 0.7129 | 0.1188 | 0.074* | |
C38 | −0.2603 (8) | 0.5817 (5) | 0.0716 (4) | 0.044 (2) | |
C39 | −0.2274 (8) | 0.5262 (6) | 0.0050 (5) | 0.052 (2) | |
H39A | −0.2516 | 0.4628 | 0.0032 | 0.062* | |
C40 | −0.1573 (9) | 0.5654 (7) | −0.0604 (5) | 0.061 (2) | |
H40A | −0.1317 | 0.5271 | −0.1048 | 0.074* | |
C41 | −0.1266 (10) | 0.6601 (8) | −0.0586 (6) | 0.070 (3) | |
H41A | −0.0865 | 0.6879 | −0.1031 | 0.084* | |
C42 | −0.2689 (9) | 0.5638 (6) | 0.2411 (4) | 0.047 (2) | |
H42A | −0.1644 | 0.5434 | 0.2323 | 0.056* | |
H42B | −0.2855 | 0.6349 | 0.2485 | 0.056* | |
C43 | −0.3169 (8) | 0.5153 (5) | 0.3154 (4) | 0.038 | |
H43A | −0.2911 | 0.4441 | 0.3106 | 0.045* | |
H43B | −0.4224 | 0.5304 | 0.3222 | 0.045* | |
C44 | −0.2487 (9) | 0.5481 (5) | 0.3879 (4) | 0.046 (2) | |
H44A | −0.1439 | 0.5438 | 0.3783 | 0.055* | |
H44B | −0.2887 | 0.6165 | 0.3992 | 0.055* | |
C45 | −0.2796 (10) | 0.4834 (6) | 0.4574 (4) | 0.054 (2) | |
H45A | −0.3809 | 0.4736 | 0.4563 | 0.065* | |
H45B | −0.2199 | 0.4192 | 0.4498 | 0.065* | |
C46 | −0.2555 (11) | 0.5170 (7) | 0.5363 (5) | 0.062 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.1248 (10) | 0.0621 (7) | 0.0723 (7) | −0.0051 (6) | −0.0086 (7) | −0.0098 (5) |
P1 | 0.0439 (13) | 0.0341 (11) | 0.0534 (13) | −0.0164 (9) | −0.0077 (10) | −0.0008 (10) |
O1 | 0.118 (6) | 0.041 (4) | 0.091 (5) | −0.040 (4) | −0.014 (4) | 0.011 (3) |
O2 | 0.144 (7) | 0.047 (4) | 0.072 (5) | −0.026 (4) | −0.016 (4) | −0.005 (3) |
C1 | 0.105 (6) | 0.107 (7) | 0.066 (5) | −0.033 (6) | 0.006 (5) | 0.000 (5) |
C2 | 0.073 (5) | 0.096 (6) | 0.069 (5) | −0.032 (5) | 0.000 (4) | −0.017 (5) |
C3 | 0.051 (4) | 0.047 (4) | 0.051 (4) | −0.022 (4) | −0.002 (3) | 0.000 (4) |
C4 | 0.047 (4) | 0.061 (5) | 0.057 (4) | −0.007 (4) | −0.003 (4) | −0.011 (4) |
C5 | 0.078 (6) | 0.081 (6) | 0.073 (5) | −0.010 (5) | −0.021 (4) | −0.017 (5) |
C6 | 0.108 (6) | 0.076 (6) | 0.058 (5) | −0.017 (5) | −0.014 (4) | −0.005 (5) |
C7 | 0.116 (7) | 0.050 (4) | 0.089 (6) | −0.013 (5) | −0.019 (5) | −0.013 (4) |
C8 | 0.071 | 0.071 | 0.071 | −0.011 | −0.003 | −0.001 |
C9 | 0.045 (4) | 0.038 (4) | 0.052 (4) | −0.009 (3) | −0.009 (4) | −0.003 (3) |
C10 | 0.083 (6) | 0.049 (4) | 0.058 (5) | −0.010 (4) | −0.018 (4) | −0.001 (4) |
C11 | 0.084 (6) | 0.063 (5) | 0.052 (5) | −0.008 (5) | −0.005 (4) | 0.006 (4) |
C12 | 0.080 (6) | 0.050 (4) | 0.079 (5) | −0.013 (4) | −0.004 (5) | 0.010 (4) |
C13 | 0.042 (5) | 0.058 (6) | 0.064 (6) | −0.024 (4) | −0.012 (4) | 0.010 (4) |
C14 | 0.040 (5) | 0.047 (5) | 0.080 (6) | −0.010 (4) | −0.011 (4) | −0.005 (5) |
C15 | 0.047 (5) | 0.032 (4) | 0.068 (6) | −0.014 (4) | −0.003 (4) | −0.004 (4) |
C16 | 0.043 (5) | 0.035 (4) | 0.050 (5) | −0.024 (4) | −0.007 (4) | −0.001 (4) |
C17 | 0.033 (5) | 0.037 (5) | 0.077 (6) | −0.014 (4) | −0.003 (4) | 0.000 (4) |
C18 | 0.059 (6) | 0.044 (5) | 0.060 (6) | −0.031 (4) | −0.010 (4) | 0.005 (4) |
C19 | 0.049 (5) | 0.026 (4) | 0.068 (6) | −0.017 (4) | −0.014 (4) | 0.000 (4) |
C20 | 0.042 (5) | 0.054 (5) | 0.066 (6) | −0.018 (4) | 0.010 (4) | −0.003 (4) |
C21 | 0.057 (6) | 0.059 (6) | 0.064 (6) | −0.004 (5) | 0.002 (5) | 0.000 (5) |
C22 | 0.073 (7) | 0.051 (6) | 0.060 (6) | −0.010 (5) | −0.004 (5) | 0.005 (5) |
C23 | 0.063 (6) | 0.045 (5) | 0.048 (5) | −0.009 (4) | 0.002 (4) | −0.007 (4) |
Br2 | 0.0661 (7) | 0.0614 (6) | 0.0733 (7) | 0.0044 (5) | −0.0272 (5) | −0.0093 (5) |
P2 | 0.0507 (14) | 0.0355 (12) | 0.0465 (13) | −0.0130 (10) | −0.0120 (10) | 0.0004 (9) |
O3 | 0.145 (6) | 0.117 (6) | 0.068 (4) | −0.063 (5) | 0.000 (4) | −0.001 (4) |
O4 | 0.109 (5) | 0.115 (5) | 0.059 (4) | −0.059 (4) | −0.008 (4) | −0.004 (4) |
C24 | 0.074 (8) | 0.087 (9) | 0.087 (8) | −0.001 (7) | −0.018 (7) | −0.025 (7) |
C25 | 0.083 (9) | 0.075 (8) | 0.098 (9) | 0.003 (7) | 0.000 (7) | 0.010 (7) |
C26 | 0.071 (7) | 0.064 (6) | 0.069 (7) | −0.003 (5) | 0.009 (5) | 0.018 (5) |
C27 | 0.058 (5) | 0.040 (5) | 0.045 (5) | −0.019 (4) | −0.011 (4) | −0.001 (4) |
C28 | 0.059 (6) | 0.055 (6) | 0.061 (6) | −0.017 (5) | −0.021 (5) | 0.000 (5) |
C29 | 0.055 (7) | 0.074 (7) | 0.085 (8) | −0.023 (5) | 0.006 (5) | −0.019 (6) |
C30 | 0.063 (7) | 0.057 (6) | 0.114 (9) | −0.024 (5) | −0.019 (6) | −0.013 (6) |
C31 | 0.058 (6) | 0.045 (5) | 0.084 (7) | −0.007 (4) | −0.022 (5) | −0.002 (5) |
C32 | 0.043 (5) | 0.028 (4) | 0.042 (4) | −0.008 (3) | −0.007 (4) | 0.004 (3) |
C33 | 0.041 (5) | 0.041 (5) | 0.073 (6) | −0.013 (4) | −0.008 (4) | −0.005 (4) |
C34 | 0.057 (6) | 0.041 (5) | 0.097 (8) | −0.005 (4) | −0.003 (5) | −0.002 (5) |
C35 | 0.084 (7) | 0.038 (5) | 0.076 (7) | −0.017 (5) | −0.001 (6) | 0.002 (5) |
C36 | 0.089 (8) | 0.049 (6) | 0.083 (8) | −0.022 (5) | 0.005 (6) | 0.009 (6) |
C37 | 0.093 (7) | 0.045 (5) | 0.049 (5) | −0.018 (5) | −0.011 (5) | −0.001 (4) |
C38 | 0.057 (5) | 0.033 (4) | 0.043 (5) | −0.006 (4) | −0.012 (4) | 0.002 (4) |
C39 | 0.045 (5) | 0.056 (6) | 0.056 (6) | −0.014 (4) | −0.004 (4) | 0.004 (5) |
C40 | 0.054 (6) | 0.080 (7) | 0.048 (5) | −0.007 (5) | 0.004 (4) | −0.014 (5) |
C41 | 0.067 (7) | 0.072 (7) | 0.076 (7) | −0.031 (6) | −0.002 (5) | 0.019 (6) |
C42 | 0.052 (5) | 0.039 (5) | 0.052 (5) | −0.011 (4) | −0.007 (4) | 0.001 (4) |
C43 | 0.038 | 0.038 | 0.038 | −0.006 | −0.002 | 0.000 |
C44 | 0.052 (5) | 0.033 (4) | 0.053 (5) | −0.005 (4) | −0.010 (4) | −0.011 (4) |
C45 | 0.070 (6) | 0.047 (5) | 0.046 (5) | −0.011 (4) | −0.007 (4) | −0.005 (4) |
C46 | 0.076 (6) | 0.066 (5) | 0.048 (5) | −0.022 (4) | −0.001 (4) | 0.002 (4) |
P1—C9 | 1.777 (8) | P2—C38 | 1.776 (8) |
P1—C3 | 1.778 (8) | P2—C27 | 1.789 (8) |
P1—C16 | 1.788 (7) | P2—C32 | 1.798 (7) |
P1—C19 | 1.814 (8) | P2—C42 | 1.818 (7) |
O1—C23 | 1.196 (9) | O3—C46 | 1.191 (10) |
O2—C23 | 1.317 (9) | O4—C46 | 1.294 (10) |
O2—H2B | 0.8200 | O4—H4B | 0.8200 |
C1—C2 | 1.373 (13) | C24—C25 | 1.366 (14) |
C1—C6 | 1.388 (11) | C24—C29 | 1.368 (13) |
C1—H1A | 0.9300 | C24—H24A | 0.9300 |
C2—C3 | 1.340 (11) | C25—C26 | 1.349 (13) |
C2—H2A | 0.9300 | C25—H25A | 0.9300 |
C3—C4 | 1.401 (10) | C26—C27 | 1.423 (11) |
C4—C5 | 1.342 (11) | C26—H26A | 0.9300 |
C4—H4A | 0.9300 | C27—C28 | 1.398 (11) |
C5—C6 | 1.340 (13) | C28—C29 | 1.388 (12) |
C5—H5A | 0.9300 | C28—H28A | 0.9300 |
C6—H6A | 0.9300 | C29—H29A | 0.9300 |
C7—C12 | 1.333 (12) | C30—C35 | 1.374 (12) |
C7—C8 | 1.423 (12) | C30—C31 | 1.391 (11) |
C7—H7A | 0.9300 | C30—H30A | 0.9300 |
C8—C9 | 1.390 (11) | C31—C32 | 1.378 (10) |
C8—H8A | 0.9300 | C31—H31A | 0.9300 |
C9—C10 | 1.358 (10) | C32—C33 | 1.384 (10) |
C10—C11 | 1.376 (11) | C33—C34 | 1.382 (10) |
C10—H10A | 0.9300 | C33—H33A | 0.9300 |
C11—C12 | 1.358 (12) | C34—C35 | 1.366 (12) |
C11—H11A | 0.9300 | C34—H34A | 0.9300 |
C12—H12A | 0.9300 | C35—H35A | 0.9300 |
C13—C18 | 1.373 (10) | C36—C41 | 1.358 (13) |
C13—C14 | 1.388 (10) | C36—C37 | 1.378 (12) |
C13—H13A | 0.9300 | C36—H36A | 0.9300 |
C14—C15 | 1.365 (10) | C37—C38 | 1.389 (10) |
C14—H14A | 0.9300 | C37—H37A | 0.9300 |
C15—C16 | 1.355 (10) | C38—C39 | 1.375 (10) |
C15—H15A | 0.9300 | C39—C40 | 1.403 (11) |
C16—C17 | 1.402 (10) | C39—H39A | 0.9300 |
C17—C18 | 1.369 (10) | C40—C41 | 1.370 (12) |
C17—H17A | 0.9300 | C40—H40A | 0.9300 |
C18—H18A | 0.9300 | C41—H41A | 0.9300 |
C19—C20 | 1.542 (10) | C42—C43 | 1.501 (10) |
C19—H19A | 0.9700 | C42—H42A | 0.9700 |
C19—H19B | 0.9700 | C42—H42B | 0.9700 |
C20—C21 | 1.512 (10) | C43—C44 | 1.524 (9) |
C20—H20A | 0.9700 | C43—H43A | 0.9700 |
C20—H20B | 0.9700 | C43—H43B | 0.9700 |
C21—C22 | 1.533 (11) | C44—C45 | 1.508 (10) |
C21—H21A | 0.9700 | C44—H44A | 0.9700 |
C21—H21B | 0.9700 | C44—H44B | 0.9700 |
C22—C23 | 1.499 (11) | C45—C46 | 1.470 (11) |
C22—H22A | 0.9700 | C45—H45A | 0.9700 |
C22—H22B | 0.9700 | C45—H45B | 0.9700 |
C9—P1—C3 | 110.4 (4) | C38—P2—C27 | 110.9 (4) |
C9—P1—C16 | 107.9 (4) | C38—P2—C32 | 109.2 (4) |
C3—P1—C16 | 110.0 (4) | C27—P2—C32 | 109.4 (3) |
C9—P1—C19 | 109.8 (4) | C38—P2—C42 | 107.4 (4) |
C3—P1—C19 | 107.5 (4) | C27—P2—C42 | 109.9 (4) |
C16—P1—C19 | 111.3 (3) | C32—P2—C42 | 110.1 (3) |
C23—O2—H2B | 109.5 | C46—O4—H4B | 109.5 |
C2—C1—C6 | 119.6 (10) | C25—C24—C29 | 120.3 (10) |
C2—C1—H1A | 120.2 | C25—C24—H24A | 119.9 |
C6—C1—H1A | 120.2 | C29—C24—H24A | 119.9 |
C3—C2—C1 | 122.3 (10) | C26—C25—C24 | 121.8 (11) |
C3—C2—H2A | 118.8 | C26—C25—H25A | 119.1 |
C1—C2—H2A | 118.8 | C24—C25—H25A | 119.1 |
C2—C3—C4 | 117.2 (8) | C25—C26—C27 | 119.6 (9) |
C2—C3—P1 | 120.4 (7) | C25—C26—H26A | 120.2 |
C4—C3—P1 | 122.4 (6) | C27—C26—H26A | 120.2 |
C5—C4—C3 | 120.1 (9) | C28—C27—C26 | 118.1 (8) |
C5—C4—H4A | 119.9 | C28—C27—P2 | 121.3 (6) |
C3—C4—H4A | 119.9 | C26—C27—P2 | 120.6 (7) |
C6—C5—C4 | 122.9 (10) | C29—C28—C27 | 120.3 (9) |
C6—C5—H5A | 118.5 | C29—C28—H28A | 119.9 |
C4—C5—H5A | 118.5 | C27—C28—H28A | 119.9 |
C5—C6—C1 | 117.7 (10) | C24—C29—C28 | 119.9 (10) |
C5—C6—H6A | 121.2 | C24—C29—H29A | 120.1 |
C1—C6—H6A | 121.2 | C28—C29—H29A | 120.1 |
C12—C7—C8 | 122.6 (9) | C35—C30—C31 | 118.7 (8) |
C12—C7—H7A | 118.7 | C35—C30—H30A | 120.7 |
C8—C7—H7A | 118.7 | C31—C30—H30A | 120.7 |
C9—C8—C7 | 117.6 (9) | C32—C31—C30 | 120.7 (8) |
C9—C8—H8A | 121.2 | C32—C31—H31A | 119.6 |
C7—C8—H8A | 121.2 | C30—C31—H31A | 119.6 |
C10—C9—C8 | 118.1 (8) | C31—C32—C33 | 119.5 (7) |
C10—C9—P1 | 121.3 (6) | C31—C32—P2 | 121.2 (6) |
C8—C9—P1 | 120.6 (6) | C33—C32—P2 | 119.1 (6) |
C9—C10—C11 | 122.6 (8) | C34—C33—C32 | 119.8 (7) |
C9—C10—H10A | 118.7 | C34—C33—H33A | 120.1 |
C11—C10—H10A | 118.7 | C32—C33—H33A | 120.1 |
C12—C11—C10 | 120.2 (9) | C35—C34—C33 | 120.1 (8) |
C12—C11—H11A | 119.9 | C35—C34—H34A | 119.9 |
C10—C11—H11A | 119.9 | C33—C34—H34A | 119.9 |
C7—C12—C11 | 118.7 (9) | C34—C35—C30 | 121.1 (8) |
C7—C12—H12A | 120.7 | C34—C35—H35A | 119.4 |
C11—C12—H12A | 120.7 | C30—C35—H35A | 119.4 |
C18—C13—C14 | 118.1 (7) | C41—C36—C37 | 120.7 (9) |
C18—C13—H13A | 121.0 | C41—C36—H36A | 119.7 |
C14—C13—H13A | 121.0 | C37—C36—H36A | 119.7 |
C15—C14—C13 | 121.2 (8) | C36—C37—C38 | 120.2 (8) |
C15—C14—H14A | 119.4 | C36—C37—H37A | 119.9 |
C13—C14—H14A | 119.4 | C38—C37—H37A | 119.9 |
C16—C15—C14 | 120.6 (7) | C39—C38—C37 | 119.1 (8) |
C16—C15—H15A | 119.7 | C39—C38—P2 | 121.0 (6) |
C14—C15—H15A | 119.7 | C37—C38—P2 | 119.8 (6) |
C15—C16—C17 | 119.1 (7) | C38—C39—C40 | 119.9 (8) |
C15—C16—P1 | 121.5 (6) | C38—C39—H39A | 120.1 |
C17—C16—P1 | 119.4 (6) | C40—C39—H39A | 120.1 |
C18—C17—C16 | 119.9 (7) | C41—C40—C39 | 119.9 (8) |
C18—C17—H17A | 120.0 | C41—C40—H40A | 120.1 |
C16—C17—H17A | 120.0 | C39—C40—H40A | 120.1 |
C17—C18—C13 | 121.0 (8) | C36—C41—C40 | 120.1 (9) |
C17—C18—H18A | 119.5 | C36—C41—H41A | 120.0 |
C13—C18—H18A | 119.5 | C40—C41—H41A | 120.0 |
C20—C19—P1 | 115.2 (5) | C43—C42—P2 | 115.9 (5) |
C20—C19—H19A | 108.5 | C43—C42—H42A | 108.3 |
P1—C19—H19A | 108.5 | P2—C42—H42A | 108.3 |
C20—C19—H19B | 108.5 | C43—C42—H42B | 108.3 |
P1—C19—H19B | 108.5 | P2—C42—H42B | 108.3 |
H19A—C19—H19B | 107.5 | H42A—C42—H42B | 107.4 |
C21—C20—C19 | 110.5 (7) | C42—C43—C44 | 113.3 (6) |
C21—C20—H20A | 109.5 | C42—C43—H43A | 108.9 |
C19—C20—H20A | 109.5 | C44—C43—H43A | 108.9 |
C21—C20—H20B | 109.5 | C42—C43—H43B | 108.9 |
C19—C20—H20B | 109.5 | C44—C43—H43B | 108.9 |
H20A—C20—H20B | 108.1 | H43A—C43—H43B | 107.7 |
C20—C21—C22 | 111.8 (7) | C45—C44—C43 | 110.2 (6) |
C20—C21—H21A | 109.3 | C45—C44—H44A | 109.6 |
C22—C21—H21A | 109.3 | C43—C44—H44A | 109.6 |
C20—C21—H21B | 109.3 | C45—C44—H44B | 109.6 |
C22—C21—H21B | 109.3 | C43—C44—H44B | 109.6 |
H21A—C21—H21B | 107.9 | H44A—C44—H44B | 108.1 |
C23—C22—C21 | 114.4 (7) | C46—C45—C44 | 118.5 (7) |
C23—C22—H22A | 108.7 | C46—C45—H45A | 107.7 |
C21—C22—H22A | 108.7 | C44—C45—H45A | 107.7 |
C23—C22—H22B | 108.7 | C46—C45—H45B | 107.7 |
C21—C22—H22B | 108.7 | C44—C45—H45B | 107.7 |
H22A—C22—H22B | 107.6 | H45A—C45—H45B | 107.1 |
O1—C23—O2 | 122.6 (8) | O3—C46—O4 | 120.7 (9) |
O1—C23—C22 | 124.9 (8) | O3—C46—C45 | 123.4 (9) |
O2—C23—C22 | 112.5 (8) | O4—C46—C45 | 115.8 (8) |
C6—C1—C2—C3 | 1.5 (17) | C29—C24—C25—C26 | −1.4 (12) |
C1—C2—C3—C4 | −1.6 (15) | C24—C25—C26—C27 | −1.0 (12) |
C1—C2—C3—P1 | 179.6 (8) | C25—C26—C27—C28 | 2.2 (12) |
C9—P1—C3—C2 | −97.1 (8) | C25—C26—C27—P2 | −177.5 (6) |
C16—P1—C3—C2 | 21.8 (9) | C38—P2—C27—C28 | 169.5 (6) |
C19—P1—C3—C2 | 143.2 (7) | C32—P2—C27—C28 | 49.0 (7) |
C9—P1—C3—C4 | 84.1 (8) | C42—P2—C27—C28 | −72.0 (7) |
C16—P1—C3—C4 | −156.9 (7) | C38—P2—C27—C26 | −10.8 (8) |
C19—P1—C3—C4 | −35.6 (8) | C32—P2—C27—C26 | −131.3 (6) |
C2—C3—C4—C5 | 2.9 (13) | C42—P2—C27—C26 | 107.8 (7) |
P1—C3—C4—C5 | −178.3 (7) | C26—C27—C28—C29 | −1.1 (12) |
C3—C4—C5—C6 | −4.4 (15) | P2—C27—C28—C29 | 178.6 (6) |
C4—C5—C6—C1 | 4.2 (16) | C25—C24—C29—C28 | 2.5 (13) |
C2—C1—C6—C5 | −2.6 (16) | C27—C28—C29—C24 | −1.2 (13) |
C12—C7—C8—C9 | −5.4 (16) | C35—C30—C31—C32 | −0.4 (15) |
C7—C8—C9—C10 | 3.7 (13) | C30—C31—C32—C33 | 0.0 (13) |
C7—C8—C9—P1 | −176.9 (7) | C30—C31—C32—P2 | 174.1 (7) |
C3—P1—C9—C10 | 171.5 (7) | C38—P2—C32—C31 | −100.5 (7) |
C16—P1—C9—C10 | 51.3 (8) | C27—P2—C32—C31 | 21.0 (8) |
C19—P1—C9—C10 | −70.2 (8) | C42—P2—C32—C31 | 141.8 (7) |
C3—P1—C9—C8 | −7.9 (8) | C38—P2—C32—C33 | 73.6 (7) |
C16—P1—C9—C8 | −128.1 (7) | C27—P2—C32—C33 | −164.9 (6) |
C19—P1—C9—C8 | 110.4 (7) | C42—P2—C32—C33 | −44.1 (7) |
C8—C9—C10—C11 | −1.3 (14) | C31—C32—C33—C34 | 0.2 (13) |
P1—C9—C10—C11 | 179.2 (7) | P2—C32—C33—C34 | −174.1 (7) |
C9—C10—C11—C12 | 0.3 (15) | C32—C33—C34—C35 | 0.0 (14) |
C8—C7—C12—C11 | 4.5 (16) | C33—C34—C35—C30 | −0.4 (15) |
C10—C11—C12—C7 | −1.9 (15) | C31—C30—C35—C34 | 0.6 (15) |
C18—C13—C14—C15 | −1.8 (13) | C41—C36—C37—C38 | 0.1 (15) |
C13—C14—C15—C16 | 1.0 (13) | C36—C37—C38—C39 | 2.1 (13) |
C14—C15—C16—C17 | 0.5 (12) | C36—C37—C38—P2 | −175.2 (7) |
C14—C15—C16—P1 | 178.4 (6) | C27—P2—C38—C39 | −103.7 (7) |
C9—P1—C16—C15 | 26.9 (8) | C32—P2—C38—C39 | 16.9 (7) |
C3—P1—C16—C15 | −93.5 (7) | C42—P2—C38—C39 | 136.3 (6) |
C19—P1—C16—C15 | 147.4 (7) | C27—P2—C38—C37 | 73.6 (7) |
C9—P1—C16—C17 | −155.1 (6) | C32—P2—C38—C37 | −165.8 (6) |
C3—P1—C16—C17 | 84.4 (7) | C42—P2—C38—C37 | −46.4 (7) |
C19—P1—C16—C17 | −34.6 (7) | C37—C38—C39—C40 | −1.0 (12) |
C15—C16—C17—C18 | −1.1 (12) | P2—C38—C39—C40 | 176.3 (6) |
P1—C16—C17—C18 | −179.1 (6) | C38—C39—C40—C41 | −2.4 (12) |
C16—C17—C18—C13 | 0.2 (13) | C37—C36—C41—C40 | −3.6 (15) |
C14—C13—C18—C17 | 1.2 (13) | C39—C40—C41—C36 | 4.7 (14) |
C9—P1—C19—C20 | 68.5 (6) | C38—P2—C42—C43 | −168.8 (5) |
C3—P1—C19—C20 | −171.4 (5) | C27—P2—C42—C43 | 70.5 (7) |
C16—P1—C19—C20 | −50.9 (7) | C32—P2—C42—C43 | −50.0 (7) |
P1—C19—C20—C21 | −178.2 (6) | P2—C42—C43—C44 | −174.5 (5) |
C19—C20—C21—C22 | −168.7 (7) | C42—C43—C44—C45 | −169.7 (6) |
C20—C21—C22—C23 | −67.3 (10) | C43—C44—C45—C46 | −165.2 (7) |
C21—C22—C23—O1 | −19.9 (13) | C44—C45—C46—O3 | 154.3 (10) |
C21—C22—C23—O2 | 161.1 (8) | C44—C45—C46—O4 | −28.9 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2B···Br1i | 0.82 | 2.35 | 3.148 (7) | 165 |
O4—H4B···Br2ii | 0.82 | 2.41 | 3.199 (7) | 163 |
C14—H14A···O1iii | 0.93 | 2.58 | 3.357 (10) | 141 |
C17—H17A···Br2iv | 0.93 | 2.77 | 3.691 (7) | 169 |
C19—H19A···Br2iv | 0.97 | 2.88 | 3.790 (7) | 157 |
C19—H19B···O1i | 0.97 | 2.41 | 3.351 (10) | 163 |
C33—H33A···Br2 | 0.93 | 2.79 | 3.623 (9) | 150 |
C37—H37A···Br1v | 0.93 | 2.82 | 3.574 (8) | 139 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+3, −y+2, −z+1; (iv) x+1, y+1, z; (v) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C23H24O2P+·Br− |
Mr | 443.29 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 9.2690 (19), 13.674 (3), 17.075 (3) |
α, β, γ (°) | 88.91 (3), 87.15 (3), 81.07 (3) |
V (Å3) | 2135.1 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.02 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.583, 0.824 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8913, 8367, 3700 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.084, 0.196, 0.99 |
No. of reflections | 8367 |
No. of parameters | 475 |
No. of restraints | 121 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.72, −0.60 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), X-CAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2B···Br1i | 0.82 | 2.35 | 3.148 (7) | 165.0 |
O4—H4B···Br2ii | 0.82 | 2.41 | 3.199 (7) | 163.0 |
C14—H14A···O1iii | 0.93 | 2.58 | 3.357 (10) | 141.0 |
C17—H17A···Br2iv | 0.93 | 2.77 | 3.691 (7) | 169.0 |
C19—H19A···Br2iv | 0.97 | 2.88 | 3.790 (7) | 157.0 |
C19—H19B···O1i | 0.97 | 2.41 | 3.351 (10) | 163.0 |
C33—H33A···Br2 | 0.93 | 2.79 | 3.623 (9) | 150.0 |
C37—H37A···Br1v | 0.93 | 2.82 | 3.574 (8) | 139.0 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+3, −y+2, −z+1; (iv) x+1, y+1, z; (v) x−1, y, z. |
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Triphenylphosphoniums are an important class of isoaromatic compounds and have widespread applications in pharmaceuticals (Mashraqui et al., 2004; Ishikawa & Manabe, 2006). As part of our ongoing studies in this area, we report herein the synthesis and crystal structure of the title compound, (I).
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The asymmetric unit contains two independent molecules. Rings A (C1–C6), B (C7–C12), C (C13–C18), D (C24–C29), E (C30–C35) and F (C36–C41) are, of course, planar and the dihedral angles between them are A/B = 79.30 (3)°, A/C = 87.03 (3)°, B/C = 63.74 (2)°, D/E = 61.30 (2)°, D/F = 70.17 (3)° and E/F = 84.32 (3)°.
In the crystal structure, O—H···Br, C—H···O and C—H···Br hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they seem to be effective in the stabilization of the structure.