In the crystal structure of the title compound, C
26H
20Cl
2OP
+·Cl
−, there are intermolecular C—H
O hydrogen bonds, and both intramolecular and intermolecular C—H
Cl hydrogen bonds.
Supporting information
CCDC reference: 245301
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.097
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.
Crystal data top
C26H20Cl2OP+·Cl− | F(000) = 1000 |
Mr = 485.74 | Dx = 1.403 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4946 reflections |
a = 12.5615 (4) Å | θ = 2.5–25.2° |
b = 10.9659 (4) Å | µ = 0.49 mm−1 |
c = 17.2638 (5) Å | T = 298 K |
β = 104.805 (1)° | Block, colorless |
V = 2299.11 (13) Å3 | 0.26 × 0.21 × 0.19 mm |
Z = 4 | |
Data collection top
Bruker APEX area-detector diffractometer | 4131 independent reflections |
Radiation source: fine-focus sealed tube | 3694 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 25.2°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −15→13 |
Tmin = 0.884, Tmax = 0.914 | k = −13→13 |
11818 measured reflections | l = −20→19 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0488P)2 + 0.8375P] where P = (Fo2 + 2Fc2)/3 |
4131 reflections | (Δ/σ)max = 0.001 |
280 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.27 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 | |
Cl1 | 0.24361 (5) | 0.02437 (6) | 0.46942 (3) | 0.05385 (17) | |
Cl2 | 0.61549 (6) | 0.25228 (6) | 0.60973 (3) | 0.0655 (2) | |
Cl3 | 0.41717 (5) | 0.40538 (5) | 0.23792 (3) | 0.04786 (16) | |
P1 | 0.22962 (4) | 0.05283 (4) | 0.14703 (3) | 0.02852 (13) | |
O1 | 0.22501 (12) | 0.01602 (15) | 0.30247 (9) | 0.0481 (4) | |
C1 | 0.34476 (19) | 0.0414 (2) | 0.03147 (14) | 0.0477 (5) | |
H1 | 0.3975 | −0.0016 | 0.0692 | 0.057* | |
C2 | 0.3552 (2) | 0.0554 (2) | −0.04595 (17) | 0.0589 (7) | |
H2 | 0.4158 | 0.0222 | −0.0600 | 0.071* | |
C3 | 0.2771 (2) | 0.1178 (2) | −0.10228 (14) | 0.0561 (7) | |
H3 | 0.2841 | 0.1249 | −0.1544 | 0.067* | |
C4 | 0.1891 (2) | 0.1693 (2) | −0.08173 (13) | 0.0530 (6) | |
H4 | 0.1370 | 0.2126 | −0.1197 | 0.064* | |
C5 | 0.17726 (18) | 0.1571 (2) | −0.00459 (12) | 0.0419 (5) | |
H5 | 0.1173 | 0.1924 | 0.0092 | 0.050* | |
C6 | 0.25464 (16) | 0.09251 (17) | 0.05215 (11) | 0.0327 (4) | |
C7 | 0.12457 (19) | 0.26426 (19) | 0.16885 (14) | 0.0452 (5) | |
H7 | 0.1916 | 0.3016 | 0.1704 | 0.054* | |
C8 | 0.0359 (2) | 0.3323 (2) | 0.17779 (16) | 0.0581 (6) | |
H8 | 0.0437 | 0.4160 | 0.1860 | 0.070* | |
C9 | −0.0634 (2) | 0.2784 (2) | 0.17482 (18) | 0.0636 (7) | |
H9 | −0.1227 | 0.3256 | 0.1802 | 0.076* | |
C10 | −0.0754 (2) | 0.1548 (2) | 0.16394 (19) | 0.0647 (7) | |
H10 | −0.1428 | 0.1182 | 0.1621 | 0.078* | |
C11 | 0.01225 (18) | 0.0843 (2) | 0.15565 (15) | 0.0479 (5) | |
H11 | 0.0041 | 0.0003 | 0.1489 | 0.058* | |
C12 | 0.11185 (15) | 0.13869 (17) | 0.15738 (11) | 0.0322 (4) | |
C13 | 0.12664 (19) | −0.1564 (2) | 0.07666 (15) | 0.0497 (6) | |
H13 | 0.0826 | −0.1040 | 0.0396 | 0.060* | |
C14 | 0.1120 (2) | −0.2811 (2) | 0.06840 (17) | 0.0612 (7) | |
H14 | 0.0573 | −0.3126 | 0.0263 | 0.073* | |
C15 | 0.1787 (2) | −0.3588 (2) | 0.12276 (16) | 0.0547 (6) | |
H15 | 0.1682 | −0.4427 | 0.1176 | 0.066* | |
C16 | 0.2606 (2) | −0.3126 (2) | 0.18443 (14) | 0.0484 (6) | |
H16 | 0.3061 | −0.3654 | 0.2203 | 0.058* | |
C17 | 0.27572 (18) | −0.18827 (19) | 0.19343 (12) | 0.0410 (5) | |
H17 | 0.3317 | −0.1574 | 0.2349 | 0.049* | |
C18 | 0.20702 (15) | −0.10935 (16) | 0.14031 (11) | 0.0316 (4) | |
C19 | 0.34558 (15) | 0.09112 (17) | 0.22925 (11) | 0.0317 (4) | |
H19A | 0.4089 | 0.0418 | 0.2271 | 0.038* | |
H19B | 0.3649 | 0.1763 | 0.2262 | 0.038* | |
C20 | 0.31270 (16) | 0.06657 (17) | 0.30704 (11) | 0.0331 (4) | |
C21 | 0.38759 (16) | 0.10597 (16) | 0.38370 (11) | 0.0312 (4) | |
C22 | 0.36295 (17) | 0.09391 (17) | 0.45809 (12) | 0.0353 (4) | |
C23 | 0.43275 (18) | 0.13783 (18) | 0.52769 (12) | 0.0397 (5) | |
H23 | 0.4153 | 0.1296 | 0.5766 | 0.048* | |
C24 | 0.52900 (18) | 0.19413 (18) | 0.52286 (12) | 0.0403 (5) | |
C25 | 0.55827 (17) | 0.20601 (19) | 0.45163 (12) | 0.0409 (5) | |
H25 | 0.6243 | 0.2430 | 0.4500 | 0.049* | |
C26 | 0.48749 (16) | 0.16186 (18) | 0.38302 (12) | 0.0366 (4) | |
H26 | 0.5066 | 0.1694 | 0.3346 | 0.044* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0564 (4) | 0.0627 (4) | 0.0486 (3) | −0.0152 (3) | 0.0248 (3) | 0.0026 (3) |
Cl2 | 0.0780 (5) | 0.0699 (4) | 0.0363 (3) | −0.0185 (3) | −0.0080 (3) | 0.0006 (3) |
Cl3 | 0.0527 (3) | 0.0405 (3) | 0.0540 (3) | −0.0029 (2) | 0.0203 (3) | 0.0055 (2) |
P1 | 0.0272 (3) | 0.0283 (2) | 0.0303 (3) | 0.00074 (19) | 0.0076 (2) | 0.00056 (19) |
O1 | 0.0445 (9) | 0.0586 (10) | 0.0410 (9) | −0.0183 (8) | 0.0104 (7) | 0.0010 (7) |
C1 | 0.0475 (13) | 0.0468 (12) | 0.0552 (14) | 0.0060 (11) | 0.0246 (11) | 0.0041 (11) |
C2 | 0.0664 (16) | 0.0559 (14) | 0.0701 (17) | −0.0088 (13) | 0.0460 (15) | −0.0116 (13) |
C3 | 0.0777 (18) | 0.0571 (14) | 0.0398 (13) | −0.0274 (14) | 0.0268 (13) | −0.0083 (11) |
C4 | 0.0603 (15) | 0.0608 (15) | 0.0343 (12) | −0.0147 (12) | 0.0052 (11) | 0.0063 (11) |
C5 | 0.0398 (12) | 0.0482 (12) | 0.0378 (11) | −0.0018 (10) | 0.0101 (9) | 0.0032 (9) |
C6 | 0.0340 (10) | 0.0311 (9) | 0.0342 (10) | −0.0038 (8) | 0.0110 (8) | −0.0021 (8) |
C7 | 0.0446 (12) | 0.0368 (11) | 0.0577 (14) | −0.0003 (10) | 0.0195 (11) | −0.0046 (10) |
C8 | 0.0660 (16) | 0.0380 (12) | 0.0762 (17) | 0.0104 (12) | 0.0292 (14) | −0.0054 (12) |
C9 | 0.0492 (15) | 0.0614 (16) | 0.087 (2) | 0.0197 (13) | 0.0298 (14) | −0.0030 (14) |
C10 | 0.0382 (13) | 0.0620 (16) | 0.101 (2) | 0.0024 (12) | 0.0301 (14) | −0.0066 (15) |
C11 | 0.0381 (12) | 0.0423 (12) | 0.0666 (15) | 0.0004 (10) | 0.0192 (11) | −0.0030 (11) |
C12 | 0.0305 (10) | 0.0342 (10) | 0.0329 (10) | 0.0046 (8) | 0.0097 (8) | 0.0011 (8) |
C13 | 0.0448 (13) | 0.0386 (12) | 0.0573 (14) | 0.0041 (10) | −0.0025 (11) | −0.0049 (10) |
C14 | 0.0546 (15) | 0.0456 (13) | 0.0761 (18) | −0.0077 (12) | 0.0035 (13) | −0.0196 (13) |
C15 | 0.0711 (17) | 0.0301 (11) | 0.0712 (17) | −0.0032 (11) | 0.0337 (14) | −0.0061 (11) |
C16 | 0.0670 (15) | 0.0363 (11) | 0.0471 (13) | 0.0116 (11) | 0.0243 (12) | 0.0082 (10) |
C17 | 0.0485 (12) | 0.0384 (11) | 0.0365 (11) | 0.0058 (10) | 0.0115 (10) | 0.0022 (9) |
C18 | 0.0317 (10) | 0.0289 (9) | 0.0358 (10) | 0.0013 (8) | 0.0113 (8) | 0.0002 (8) |
C19 | 0.0295 (10) | 0.0327 (10) | 0.0317 (10) | −0.0011 (8) | 0.0056 (8) | −0.0012 (8) |
C20 | 0.0361 (11) | 0.0280 (9) | 0.0352 (10) | 0.0009 (8) | 0.0091 (8) | 0.0029 (8) |
C21 | 0.0347 (10) | 0.0275 (9) | 0.0315 (10) | 0.0031 (8) | 0.0085 (8) | 0.0030 (8) |
C22 | 0.0405 (11) | 0.0294 (9) | 0.0376 (11) | 0.0022 (8) | 0.0129 (9) | 0.0046 (8) |
C23 | 0.0545 (13) | 0.0356 (10) | 0.0293 (10) | 0.0042 (10) | 0.0111 (9) | 0.0042 (8) |
C24 | 0.0494 (13) | 0.0346 (10) | 0.0313 (11) | 0.0007 (10) | 0.0000 (9) | 0.0017 (8) |
C25 | 0.0367 (11) | 0.0424 (11) | 0.0402 (12) | −0.0042 (9) | 0.0038 (9) | 0.0042 (9) |
C26 | 0.0374 (11) | 0.0409 (11) | 0.0317 (10) | 0.0006 (9) | 0.0090 (9) | 0.0024 (9) |
Geometric parameters (Å, º) top
Cl1—C22 | 1.737 (2) | C11—C12 | 1.380 (3) |
Cl2—C24 | 1.733 (2) | C11—H11 | 0.930 |
P1—C6 | 1.7984 (19) | C13—C14 | 1.382 (3) |
P1—C18 | 1.8000 (19) | C13—C18 | 1.388 (3) |
P1—C12 | 1.8006 (18) | C13—H13 | 0.930 |
P1—C19 | 1.8044 (19) | C14—C15 | 1.381 (4) |
O1—C20 | 1.218 (2) | C14—H14 | 0.930 |
C1—C2 | 1.384 (3) | C15—C16 | 1.374 (3) |
C1—C6 | 1.389 (3) | C15—H15 | 0.930 |
C1—H1 | 0.930 | C16—C17 | 1.380 (3) |
C2—C3 | 1.374 (4) | C16—H16 | 0.930 |
C2—H2 | 0.930 | C17—C18 | 1.389 (3) |
C3—C4 | 1.366 (4) | C17—H17 | 0.930 |
C3—H3 | 0.930 | C19—C20 | 1.526 (3) |
C4—C5 | 1.384 (3) | C19—H19A | 0.970 |
C4—H4 | 0.930 | C19—H19B | 0.970 |
C5—C6 | 1.385 (3) | C20—C21 | 1.479 (3) |
C5—H5 | 0.930 | C21—C26 | 1.399 (3) |
C7—C8 | 1.382 (3) | C21—C22 | 1.402 (3) |
C7—C12 | 1.395 (3) | C22—C23 | 1.381 (3) |
C7—H7 | 0.930 | C23—C24 | 1.379 (3) |
C8—C9 | 1.369 (4) | C23—H23 | 0.930 |
C8—H8 | 0.930 | C24—C25 | 1.377 (3) |
C9—C10 | 1.372 (4) | C25—C26 | 1.375 (3) |
C9—H9 | 0.930 | C25—H25 | 0.930 |
C10—C11 | 1.382 (3) | C26—H26 | 0.930 |
C10—H10 | 0.930 | | |
| | | |
C6—P1—C18 | 103.99 (9) | C18—C13—H13 | 120.0 |
C6—P1—C12 | 107.65 (9) | C15—C14—C13 | 119.9 (2) |
C18—P1—C12 | 113.76 (9) | C15—C14—H14 | 120.0 |
C6—P1—C19 | 111.49 (9) | C13—C14—H14 | 120.0 |
C18—P1—C19 | 111.28 (9) | C16—C15—C14 | 120.2 (2) |
C12—P1—C19 | 108.59 (9) | C16—C15—H15 | 119.9 |
C2—C1—C6 | 119.2 (2) | C14—C15—H15 | 119.9 |
C2—C1—H1 | 120.4 | C15—C16—C17 | 120.4 (2) |
C6—C1—H1 | 120.4 | C15—C16—H16 | 119.8 |
C3—C2—C1 | 120.8 (2) | C17—C16—H16 | 119.8 |
C3—C2—H2 | 119.6 | C16—C17—C18 | 119.8 (2) |
C1—C2—H2 | 119.6 | C16—C17—H17 | 120.1 |
C4—C3—C2 | 120.0 (2) | C18—C17—H17 | 120.1 |
C4—C3—H3 | 120.0 | C13—C18—C17 | 119.65 (18) |
C2—C3—H3 | 120.0 | C13—C18—P1 | 119.27 (15) |
C3—C4—C5 | 120.2 (2) | C17—C18—P1 | 120.78 (15) |
C3—C4—H4 | 119.9 | C20—C19—P1 | 107.79 (13) |
C5—C4—H4 | 119.9 | C20—C19—H19A | 110.1 |
C4—C5—C6 | 120.1 (2) | P1—C19—H19A | 110.1 |
C4—C5—H5 | 120.0 | C20—C19—H19B | 110.1 |
C6—C5—H5 | 120.0 | P1—C19—H19B | 110.1 |
C5—C6—C1 | 119.67 (19) | H19A—C19—H19B | 108.5 |
C5—C6—P1 | 120.89 (15) | O1—C20—C21 | 123.30 (17) |
C1—C6—P1 | 118.70 (16) | O1—C20—C19 | 117.84 (17) |
C8—C7—C12 | 118.8 (2) | C21—C20—C19 | 118.85 (16) |
C8—C7—H7 | 120.6 | C26—C21—C22 | 117.21 (18) |
C12—C7—H7 | 120.6 | C26—C21—C20 | 119.16 (17) |
C9—C8—C7 | 121.1 (2) | C22—C21—C20 | 123.60 (17) |
C9—C8—H8 | 119.5 | C23—C22—C21 | 121.64 (19) |
C7—C8—H8 | 119.5 | C23—C22—Cl1 | 115.44 (15) |
C8—C9—C10 | 119.9 (2) | C21—C22—Cl1 | 122.91 (16) |
C8—C9—H9 | 120.1 | C24—C23—C22 | 118.37 (18) |
C10—C9—H9 | 120.1 | C24—C23—H23 | 120.8 |
C9—C10—C11 | 120.3 (2) | C22—C23—H23 | 120.8 |
C9—C10—H10 | 119.8 | C25—C24—C23 | 122.33 (19) |
C11—C10—H10 | 119.8 | C25—C24—Cl2 | 119.12 (17) |
C12—C11—C10 | 119.9 (2) | C23—C24—Cl2 | 118.55 (16) |
C12—C11—H11 | 120.1 | C26—C25—C24 | 118.34 (19) |
C10—C11—H11 | 120.1 | C26—C25—H25 | 120.8 |
C11—C12—C7 | 120.04 (18) | C24—C25—H25 | 120.8 |
C11—C12—P1 | 122.36 (15) | C25—C26—C21 | 122.08 (18) |
C7—C12—P1 | 117.59 (15) | C25—C26—H26 | 119.0 |
C14—C13—C18 | 120.0 (2) | C21—C26—H26 | 119.0 |
C14—C13—H13 | 120.0 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···Cl3i | 0.93 | 2.82 | 3.640 (2) | 148 |
C9—H9···O1ii | 0.93 | 2.51 | 3.386 (3) | 157 |
C17—H17···Cl2iii | 0.93 | 2.79 | 3.396 (2) | 123 |
C19—H19A···Cl3iv | 0.97 | 2.59 | 3.534 (2) | 165 |
C19—H19B···Cl3 | 0.97 | 2.59 | 3.555 (2) | 173 |
C23—H23···Cl3v | 0.93 | 2.80 | 3.715 (2) | 166 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, −y, −z+1; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |