The molecule of the title salt, C
26H
22OP
+.C
4H
3O
4−, consists of a benzoylmethyltriphenylphosphonium cation (HBPPY) and a hydrogen maleate anion. Owing to a strong O—H
O intraionic hydrogen bond, each hydrogen maleate ion forms a ring, described by the graph-set notation
S11(7). Several C—H
O interactions are present between the cations and anions and contribute to the stabilization of the crystal structure.
Supporting information
CCDC reference: 234845
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.106
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.820 0.975
Tmin' and Tmax expected: 0.949 0.975
RR' = 0.864
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Benzoylmethyltriphenylphosphonium hydrogenmaleate
top
Crystal data top
C26H22OP+·C4H3O4− | Dx = 1.328 Mg m−3 |
Mr = 496.47 | Melting point: 413 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 973 reflections |
a = 10.5582 (5) Å | θ = 2.3–27.0° |
b = 19.5961 (8) Å | µ = 0.15 mm−1 |
c = 24.0030 (11) Å | T = 120 K |
V = 4966.2 (4) Å3 | Block, colourless |
Z = 8 | 0.34 × 0.29 × 0.17 mm |
F(000) = 2080 | |
Data collection top
Bruker SMART CCD 6K area-detector diffractometer | 5704 independent reflections |
Radiation source: fine-focus sealed tube | 4255 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
Detector resolution: 8 pixels mm-1 | θmax = 27.5°, θmin = 1.7° |
ω scans | h = −13→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | k = −25→23 |
Tmin = 0.820, Tmax = 0.975 | l = −31→30 |
36772 measured reflections | |
Refinement top
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)] = 0.041 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.106 | All H-atom parameters refined |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0326P)2 + 2.7423P] where P = (Fo2 + 2Fc2)/3 |
5704 reflections | (Δ/σ)max < 0.001 |
425 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.07926 (4) | 0.08182 (2) | 0.668013 (17) | 0.02209 (11) | |
C1 | 0.12537 (15) | −0.05703 (8) | 0.79639 (7) | 0.0244 (3) | |
C2 | 0.20776 (17) | −0.05985 (10) | 0.84150 (8) | 0.0346 (4) | |
H2 | 0.277 (2) | −0.0297 (11) | 0.8435 (9) | 0.051 (6)* | |
C3 | 0.18939 (18) | −0.10682 (11) | 0.88364 (8) | 0.0387 (4) | |
H3 | 0.246 (2) | −0.1095 (10) | 0.9141 (9) | 0.041 (6)* | |
C4 | 0.08858 (19) | −0.15212 (9) | 0.88077 (8) | 0.0367 (4) | |
H4 | 0.0750 (18) | −0.1864 (9) | 0.9096 (8) | 0.034 (5)* | |
C5 | 0.0062 (2) | −0.14953 (10) | 0.83594 (8) | 0.0382 (4) | |
H5 | −0.067 (2) | −0.1793 (11) | 0.8332 (10) | 0.052 (6)* | |
C6 | 0.02354 (17) | −0.10196 (9) | 0.79383 (8) | 0.0316 (4) | |
H6 | −0.0353 (18) | −0.1012 (9) | 0.7623 (8) | 0.032 (5)* | |
C7 | 0.14983 (14) | −0.00508 (8) | 0.75298 (7) | 0.0233 (3) | |
C8 | 0.05025 (15) | 0.00587 (8) | 0.70838 (7) | 0.0225 (3) | |
H8A | −0.0353 (18) | 0.0105 (9) | 0.7243 (8) | 0.030 (5)* | |
H8B | 0.047 (2) | −0.0345 (11) | 0.6831 (9) | 0.046 (6)* | |
C9 | −0.05591 (15) | 0.09462 (8) | 0.62374 (7) | 0.0272 (4) | |
C10 | −0.0781 (2) | 0.04718 (10) | 0.58145 (8) | 0.0390 (4) | |
H10 | −0.023 (2) | 0.0102 (11) | 0.5773 (9) | 0.043 (6)* | |
C11 | −0.1790 (2) | 0.05661 (12) | 0.54539 (10) | 0.0482 (5) | |
H11 | −0.192 (2) | 0.0248 (12) | 0.5178 (10) | 0.053 (7)* | |
C12 | −0.25651 (19) | 0.11300 (12) | 0.55126 (9) | 0.0484 (6) | |
H12 | −0.325 (2) | 0.1194 (11) | 0.5241 (10) | 0.050 (6)* | |
C13 | −0.2350 (2) | 0.15959 (13) | 0.59294 (10) | 0.0508 (6) | |
H13 | −0.290 (2) | 0.1981 (12) | 0.5972 (11) | 0.065 (7)* | |
C14 | −0.13463 (18) | 0.15106 (11) | 0.62964 (8) | 0.0386 (4) | |
H14 | −0.119 (2) | 0.1856 (12) | 0.6584 (10) | 0.055 (7)* | |
C15 | 0.09654 (15) | 0.15199 (8) | 0.71576 (7) | 0.0259 (3) | |
C16 | 0.01554 (18) | 0.15627 (10) | 0.76133 (9) | 0.0378 (4) | |
H16 | −0.051 (2) | 0.1243 (10) | 0.7644 (9) | 0.044 (6)* | |
C17 | 0.03165 (19) | 0.20852 (11) | 0.79980 (10) | 0.0444 (5) | |
H17 | −0.023 (2) | 0.2102 (12) | 0.8326 (11) | 0.061 (7)* | |
C18 | 0.12595 (19) | 0.25625 (10) | 0.79270 (9) | 0.0388 (4) | |
H18 | 0.1354 (19) | 0.2917 (10) | 0.8194 (9) | 0.041 (6)* | |
C19 | 0.20586 (19) | 0.25250 (9) | 0.74757 (9) | 0.0376 (4) | |
H19 | 0.269 (2) | 0.2850 (11) | 0.7412 (10) | 0.056 (7)* | |
C20 | 0.19149 (17) | 0.20035 (9) | 0.70861 (8) | 0.0311 (4) | |
H20 | 0.249 (2) | 0.1979 (10) | 0.6772 (9) | 0.036 (5)* | |
C21 | 0.21235 (14) | 0.07272 (8) | 0.62209 (7) | 0.0249 (3) | |
C22 | 0.22264 (18) | 0.11835 (9) | 0.57764 (7) | 0.0314 (4) | |
H22 | 0.1616 (19) | 0.1536 (10) | 0.5732 (8) | 0.038 (5)* | |
C23 | 0.3218 (2) | 0.11160 (9) | 0.53999 (8) | 0.0376 (4) | |
H23 | 0.326 (2) | 0.1429 (11) | 0.5081 (9) | 0.048 (6)* | |
C24 | 0.40862 (18) | 0.05970 (10) | 0.54626 (8) | 0.0379 (4) | |
H24 | 0.477 (2) | 0.0556 (11) | 0.5197 (10) | 0.048 (6)* | |
C25 | 0.39807 (18) | 0.01380 (11) | 0.58970 (8) | 0.0390 (4) | |
H25 | 0.458 (2) | −0.0218 (11) | 0.5930 (9) | 0.046 (6)* | |
C26 | 0.29967 (16) | 0.01984 (9) | 0.62795 (8) | 0.0328 (4) | |
H26 | 0.2923 (18) | −0.0142 (10) | 0.6578 (8) | 0.034 (5)* | |
C27 | 1.00604 (18) | 0.21784 (9) | 0.48101 (8) | 0.0376 (4) | |
C28 | 0.87176 (18) | 0.21626 (9) | 0.46199 (8) | 0.0326 (4) | |
H28 | 0.8221 (18) | 0.2422 (10) | 0.4850 (9) | 0.038 (5)* | |
C29 | 0.81817 (18) | 0.18673 (9) | 0.41798 (8) | 0.0325 (4) | |
H29 | 0.729 (2) | 0.1930 (10) | 0.4135 (9) | 0.042 (6)* | |
C30 | 0.87435 (17) | 0.14243 (9) | 0.37351 (8) | 0.0314 (4) | |
O1 | 0.24667 (11) | 0.02886 (6) | 0.75232 (5) | 0.0298 (3) | |
O2 | 1.08911 (13) | 0.18012 (8) | 0.45561 (7) | 0.0507 (4) | |
H1 | 1.043 (3) | 0.1521 (16) | 0.4232 (14) | 0.097 (10)* | |
O3 | 1.03557 (14) | 0.25455 (8) | 0.51998 (7) | 0.0559 (4) | |
O4 | 0.80859 (13) | 0.12865 (7) | 0.33260 (6) | 0.0406 (3) | |
O5 | 0.98781 (12) | 0.11955 (7) | 0.37990 (6) | 0.0417 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.01906 (19) | 0.0239 (2) | 0.0233 (2) | 0.00029 (15) | −0.00039 (15) | 0.00196 (16) |
C1 | 0.0225 (8) | 0.0283 (8) | 0.0222 (8) | 0.0032 (6) | 0.0021 (6) | 0.0011 (6) |
C2 | 0.0220 (8) | 0.0507 (11) | 0.0312 (10) | −0.0017 (8) | −0.0007 (7) | 0.0101 (8) |
C3 | 0.0275 (9) | 0.0593 (12) | 0.0293 (10) | 0.0064 (8) | −0.0013 (8) | 0.0140 (9) |
C4 | 0.0443 (11) | 0.0348 (9) | 0.0308 (10) | 0.0081 (8) | 0.0082 (8) | 0.0100 (8) |
C5 | 0.0470 (11) | 0.0340 (9) | 0.0336 (10) | −0.0104 (8) | 0.0032 (9) | 0.0030 (8) |
C6 | 0.0349 (10) | 0.0330 (9) | 0.0268 (9) | −0.0054 (7) | −0.0026 (7) | 0.0011 (7) |
C7 | 0.0210 (8) | 0.0266 (8) | 0.0225 (8) | 0.0026 (6) | 0.0010 (6) | −0.0001 (6) |
C8 | 0.0214 (8) | 0.0247 (8) | 0.0215 (8) | −0.0005 (6) | −0.0003 (6) | 0.0026 (6) |
C9 | 0.0217 (8) | 0.0327 (8) | 0.0271 (9) | −0.0035 (6) | −0.0025 (6) | 0.0081 (7) |
C10 | 0.0409 (11) | 0.0348 (10) | 0.0413 (11) | −0.0043 (8) | −0.0135 (9) | 0.0052 (8) |
C11 | 0.0517 (13) | 0.0474 (12) | 0.0453 (13) | −0.0188 (10) | −0.0207 (10) | 0.0093 (10) |
C12 | 0.0281 (10) | 0.0718 (15) | 0.0453 (13) | −0.0107 (10) | −0.0102 (9) | 0.0245 (11) |
C13 | 0.0311 (11) | 0.0746 (15) | 0.0465 (13) | 0.0174 (11) | −0.0031 (9) | 0.0132 (11) |
C14 | 0.0308 (10) | 0.0502 (11) | 0.0347 (10) | 0.0111 (8) | −0.0017 (8) | 0.0032 (9) |
C15 | 0.0234 (8) | 0.0247 (8) | 0.0298 (9) | 0.0038 (6) | −0.0023 (6) | −0.0001 (6) |
C16 | 0.0277 (9) | 0.0428 (10) | 0.0430 (11) | −0.0047 (8) | 0.0067 (8) | −0.0121 (9) |
C17 | 0.0342 (10) | 0.0521 (12) | 0.0470 (13) | 0.0008 (9) | 0.0056 (9) | −0.0179 (10) |
C18 | 0.0402 (11) | 0.0329 (9) | 0.0432 (11) | 0.0053 (8) | −0.0106 (9) | −0.0099 (9) |
C19 | 0.0431 (11) | 0.0286 (9) | 0.0411 (11) | −0.0060 (8) | −0.0111 (9) | 0.0033 (8) |
C20 | 0.0304 (9) | 0.0316 (9) | 0.0313 (10) | −0.0016 (7) | −0.0034 (7) | 0.0043 (7) |
C21 | 0.0228 (8) | 0.0290 (8) | 0.0229 (8) | −0.0032 (6) | 0.0015 (6) | −0.0007 (6) |
C22 | 0.0396 (10) | 0.0276 (8) | 0.0270 (9) | −0.0007 (7) | 0.0025 (7) | 0.0010 (7) |
C23 | 0.0525 (12) | 0.0304 (9) | 0.0298 (10) | −0.0083 (8) | 0.0121 (8) | −0.0004 (8) |
C24 | 0.0358 (10) | 0.0434 (10) | 0.0344 (10) | −0.0098 (8) | 0.0135 (8) | −0.0096 (8) |
C25 | 0.0288 (10) | 0.0477 (11) | 0.0405 (11) | 0.0071 (8) | 0.0049 (8) | −0.0027 (9) |
C26 | 0.0275 (9) | 0.0381 (10) | 0.0328 (10) | 0.0054 (7) | 0.0034 (7) | 0.0046 (8) |
C27 | 0.0376 (10) | 0.0373 (10) | 0.0378 (10) | 0.0019 (8) | 0.0044 (8) | −0.0075 (8) |
C28 | 0.0341 (9) | 0.0279 (9) | 0.0358 (10) | 0.0047 (7) | 0.0089 (8) | −0.0015 (7) |
C29 | 0.0293 (9) | 0.0313 (9) | 0.0369 (10) | 0.0054 (7) | 0.0071 (7) | 0.0024 (7) |
C30 | 0.0352 (9) | 0.0275 (8) | 0.0316 (10) | 0.0017 (7) | 0.0051 (8) | 0.0033 (7) |
O1 | 0.0219 (6) | 0.0354 (6) | 0.0320 (6) | −0.0043 (5) | −0.0018 (5) | 0.0051 (5) |
O2 | 0.0348 (8) | 0.0650 (10) | 0.0525 (9) | 0.0128 (7) | −0.0034 (6) | −0.0270 (8) |
O3 | 0.0452 (9) | 0.0655 (10) | 0.0571 (10) | 0.0014 (7) | 0.0001 (7) | −0.0298 (8) |
O4 | 0.0445 (8) | 0.0421 (7) | 0.0353 (8) | 0.0059 (6) | −0.0030 (6) | −0.0025 (6) |
O5 | 0.0350 (7) | 0.0455 (8) | 0.0446 (8) | 0.0121 (6) | −0.0007 (6) | −0.0152 (6) |
Geometric parameters (Å, º) top
P1—C21 | 1.7949 (16) | C15—C16 | 1.391 (3) |
P1—C9 | 1.7970 (16) | C16—C17 | 1.389 (3) |
P1—C15 | 1.7993 (17) | C16—H16 | 0.95 (2) |
P1—C8 | 1.8020 (16) | C17—C18 | 1.377 (3) |
C1—C2 | 1.390 (2) | C17—H17 | 0.98 (3) |
C1—C6 | 1.391 (2) | C18—C19 | 1.375 (3) |
C1—C7 | 1.480 (2) | C18—H18 | 0.95 (2) |
C2—C3 | 1.381 (3) | C19—C20 | 1.394 (3) |
C2—H2 | 0.94 (2) | C19—H19 | 0.93 (2) |
C3—C4 | 1.388 (3) | C20—H20 | 0.97 (2) |
C3—H3 | 0.94 (2) | C21—C26 | 1.394 (2) |
C4—C5 | 1.385 (3) | C21—C22 | 1.396 (2) |
C4—H4 | 0.98 (2) | C22—C23 | 1.389 (3) |
C5—C6 | 1.387 (3) | C22—H22 | 0.95 (2) |
C5—H5 | 0.97 (2) | C23—C24 | 1.378 (3) |
C6—H6 | 0.98 (2) | C23—H23 | 0.98 (2) |
C7—O1 | 1.2198 (19) | C24—C25 | 1.382 (3) |
C7—C8 | 1.516 (2) | C24—H24 | 0.96 (2) |
C8—H8A | 0.984 (19) | C25—C26 | 1.391 (3) |
C8—H8B | 1.00 (2) | C25—H25 | 0.95 (2) |
C9—C14 | 1.391 (3) | C26—H26 | 0.98 (2) |
C9—C10 | 1.396 (3) | C27—O3 | 1.221 (2) |
C10—C11 | 1.385 (3) | C27—O2 | 1.299 (2) |
C10—H10 | 0.93 (2) | C27—C28 | 1.490 (3) |
C11—C12 | 1.382 (3) | C28—C29 | 1.331 (3) |
C11—H11 | 0.92 (2) | C28—H28 | 0.92 (2) |
C12—C13 | 1.373 (3) | C29—C30 | 1.498 (2) |
C12—H12 | 0.98 (2) | C29—H29 | 0.96 (2) |
C13—C14 | 1.388 (3) | C30—O4 | 1.233 (2) |
C13—H13 | 0.96 (2) | C30—O5 | 1.288 (2) |
C14—H14 | 0.98 (2) | O2—H1 | 1.07 (3) |
C15—C20 | 1.390 (2) | | |
| | | |
C21—P1—C9 | 105.81 (8) | C9—C14—H14 | 121.4 (14) |
C21—P1—C15 | 112.81 (8) | C20—C15—C16 | 119.96 (16) |
C9—P1—C15 | 110.52 (8) | C20—C15—P1 | 121.03 (13) |
C21—P1—C8 | 112.41 (8) | C16—C15—P1 | 118.98 (13) |
C9—P1—C8 | 107.36 (7) | C17—C16—C15 | 119.46 (18) |
C15—P1—C8 | 107.81 (8) | C17—C16—H16 | 121.8 (13) |
C2—C1—C6 | 119.54 (16) | C15—C16—H16 | 118.7 (13) |
C2—C1—C7 | 117.82 (15) | C18—C17—C16 | 120.46 (19) |
C6—C1—C7 | 122.64 (15) | C18—C17—H17 | 120.3 (14) |
C3—C2—C1 | 120.60 (18) | C16—C17—H17 | 119.2 (14) |
C3—C2—H2 | 119.4 (14) | C19—C18—C17 | 120.33 (18) |
C1—C2—H2 | 120.0 (14) | C19—C18—H18 | 120.4 (13) |
C2—C3—C4 | 119.84 (18) | C17—C18—H18 | 119.3 (13) |
C2—C3—H3 | 121.1 (13) | C18—C19—C20 | 120.07 (18) |
C4—C3—H3 | 119.1 (13) | C18—C19—H19 | 122.0 (14) |
C5—C4—C3 | 119.81 (17) | C20—C19—H19 | 117.9 (15) |
C5—C4—H4 | 119.0 (12) | C15—C20—C19 | 119.71 (18) |
C3—C4—H4 | 121.2 (12) | C15—C20—H20 | 120.8 (12) |
C4—C5—C6 | 120.52 (18) | C19—C20—H20 | 119.5 (12) |
C4—C5—H5 | 122.0 (14) | C26—C21—C22 | 120.11 (16) |
C6—C5—H5 | 117.4 (14) | C26—C21—P1 | 121.98 (13) |
C5—C6—C1 | 119.69 (17) | C22—C21—P1 | 117.81 (13) |
C5—C6—H6 | 119.3 (11) | C23—C22—C21 | 119.65 (17) |
C1—C6—H6 | 121.0 (11) | C23—C22—H22 | 120.4 (12) |
O1—C7—C1 | 122.05 (14) | C21—C22—H22 | 119.9 (12) |
O1—C7—C8 | 119.67 (14) | C24—C23—C22 | 120.05 (18) |
C1—C7—C8 | 118.28 (13) | C24—C23—H23 | 121.0 (13) |
C7—C8—P1 | 112.26 (11) | C22—C23—H23 | 118.9 (13) |
C7—C8—H8A | 112.1 (11) | C23—C24—C25 | 120.63 (17) |
P1—C8—H8A | 106.7 (10) | C23—C24—H24 | 119.1 (13) |
C7—C8—H8B | 109.8 (12) | C25—C24—H24 | 120.3 (13) |
P1—C8—H8B | 109.4 (12) | C24—C25—C26 | 120.18 (18) |
H8A—C8—H8B | 106.4 (16) | C24—C25—H25 | 119.3 (13) |
C14—C9—C10 | 120.22 (17) | C26—C25—H25 | 120.5 (13) |
C14—C9—P1 | 121.70 (14) | C25—C26—C21 | 119.37 (17) |
C10—C9—P1 | 118.05 (13) | C25—C26—H26 | 118.9 (11) |
C11—C10—C9 | 119.6 (2) | C21—C26—H26 | 121.7 (11) |
C11—C10—H10 | 120.9 (13) | O3—C27—O2 | 121.51 (19) |
C9—C10—H10 | 119.5 (13) | O3—C27—C28 | 119.36 (17) |
C12—C11—C10 | 119.9 (2) | O2—C27—C28 | 119.13 (17) |
C12—C11—H11 | 122.0 (14) | C29—C28—C27 | 131.07 (17) |
C10—C11—H11 | 118.2 (14) | C29—C28—H28 | 118.5 (13) |
C13—C12—C11 | 120.54 (19) | C27—C28—H28 | 110.4 (12) |
C13—C12—H12 | 121.4 (13) | C28—C29—C30 | 130.47 (18) |
C11—C12—H12 | 118.0 (13) | C28—C29—H29 | 116.8 (12) |
C12—C13—C14 | 120.5 (2) | C30—C29—H29 | 112.7 (12) |
C12—C13—H13 | 120.1 (15) | O4—C30—O5 | 122.85 (17) |
C14—C13—H13 | 119.3 (16) | O4—C30—C29 | 118.13 (17) |
C13—C14—C9 | 119.2 (2) | O5—C30—C29 | 119.02 (16) |
C13—C14—H14 | 119.4 (14) | C27—O2—H1 | 109.1 (17) |
| | | |
C6—C1—C2—C3 | 0.1 (3) | C9—P1—C15—C20 | −106.19 (14) |
C7—C1—C2—C3 | 179.44 (17) | C8—P1—C15—C20 | 136.75 (14) |
C1—C2—C3—C4 | 0.6 (3) | C21—P1—C15—C16 | −166.01 (14) |
C2—C3—C4—C5 | −0.6 (3) | C9—P1—C15—C16 | 75.76 (16) |
C3—C4—C5—C6 | 0.0 (3) | C8—P1—C15—C16 | −41.29 (16) |
C4—C5—C6—C1 | 0.7 (3) | C20—C15—C16—C17 | −0.9 (3) |
C2—C1—C6—C5 | −0.7 (3) | P1—C15—C16—C17 | 177.15 (16) |
C7—C1—C6—C5 | 179.92 (16) | C15—C16—C17—C18 | 0.8 (3) |
C2—C1—C7—O1 | 9.0 (2) | C16—C17—C18—C19 | −0.4 (3) |
C6—C1—C7—O1 | −171.66 (16) | C17—C18—C19—C20 | 0.2 (3) |
C2—C1—C7—C8 | −170.76 (15) | C16—C15—C20—C19 | 0.7 (3) |
C6—C1—C7—C8 | 8.6 (2) | P1—C15—C20—C19 | −177.30 (14) |
O1—C7—C8—P1 | −11.78 (19) | C18—C19—C20—C15 | −0.4 (3) |
C1—C7—C8—P1 | 167.98 (11) | C9—P1—C21—C26 | −131.84 (15) |
C21—P1—C8—C7 | 71.77 (13) | C15—P1—C21—C26 | 107.21 (15) |
C9—P1—C8—C7 | −172.28 (11) | C8—P1—C21—C26 | −14.96 (17) |
C15—P1—C8—C7 | −53.19 (13) | C9—P1—C21—C22 | 44.54 (15) |
C21—P1—C9—C14 | −124.73 (15) | C15—P1—C21—C22 | −76.41 (15) |
C15—P1—C9—C14 | −2.30 (17) | C8—P1—C21—C22 | 161.42 (13) |
C8—P1—C9—C14 | 115.04 (15) | C26—C21—C22—C23 | −1.3 (3) |
C21—P1—C9—C10 | 53.15 (16) | P1—C21—C22—C23 | −177.76 (14) |
C15—P1—C9—C10 | 175.57 (14) | C21—C22—C23—C24 | 0.6 (3) |
C8—P1—C9—C10 | −67.09 (16) | C22—C23—C24—C25 | 0.2 (3) |
C14—C9—C10—C11 | 0.0 (3) | C23—C24—C25—C26 | −0.4 (3) |
P1—C9—C10—C11 | −177.92 (16) | C24—C25—C26—C21 | −0.2 (3) |
C9—C10—C11—C12 | 0.4 (3) | C22—C21—C26—C25 | 1.1 (3) |
C10—C11—C12—C13 | −0.6 (3) | P1—C21—C26—C25 | 177.40 (14) |
C11—C12—C13—C14 | 0.4 (3) | O3—C27—C28—C29 | 172.3 (2) |
C12—C13—C14—C9 | −0.1 (3) | O2—C27—C28—C29 | −7.6 (3) |
C10—C9—C14—C13 | −0.1 (3) | C27—C28—C29—C30 | 2.7 (3) |
P1—C9—C14—C13 | 177.68 (16) | C28—C29—C30—O4 | −170.25 (19) |
C21—P1—C15—C20 | 12.04 (16) | C28—C29—C30—O5 | 10.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2i | 0.94 (2) | 2.44 (2) | 3.243 (2) | 143.0 (16) |
C4—H4···O3ii | 0.98 (2) | 2.36 (2) | 3.277 (2) | 156.8 (16) |
C8—H8A···O1iii | 0.984 (19) | 2.397 (19) | 3.371 (2) | 170.3 (15) |
C8—H8B···O4iv | 1.00 (2) | 2.42 (2) | 3.184 (2) | 132.9 (16) |
C8—H8B···O5iv | 1.00 (2) | 2.28 (2) | 3.270 (2) | 171.0 (17) |
C26—H26···O4iv | 0.98 (2) | 2.494 (19) | 3.267 (2) | 135.4 (15) |
C19—H19···O4v | 0.93 (2) | 2.49 (2) | 3.210 (2) | 134.8 (19) |
C26—H26···O1 | 0.98 (2) | 2.47 (2) | 3.042 (2) | 117.1 (14) |
O2—H1···O5 | 1.07 (3) | 1.35 (3) | 2.4197 (19) | 176 (3) |
Symmetry codes: (i) −x+3/2, −y, z+1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) x−1/2, y, −z+3/2; (iv) −x+1, −y, −z+1; (v) x−1/2, −y+1/2, −z+1. |